Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2003

data_global
_publ_contact_author_email       fonari.xray@phys.asm.md
_publ_contact_author_name        'Marina Fonari'
_journal_name_full               Org.Biomol.Chem.
_journal_coden_Cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
Y.A.Simonov
M.S.Fonari
M.J.Zaworotko
H.Abourahma
J.Lipkowski
;
E.V.Ganin
;
A.A.Yavolovskii

data_compound_1
_database_code_CSD               202644

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4,7,10,13-pentaoxacyclopentadecane ethanedithioamide clathrate
;
_chemical_name_common            
;1,4,7,10,13-pentaoxacyclopentadecane ethanedithioamide
clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H20 O5 , C2 H4 N2 S2'
_chemical_formula_sum            'C12 H24 N2 O5 S2'
_chemical_formula_weight         340.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2660(5)
_cell_length_b                   8.6440(6)
_cell_length_c                   12.5320(10)
_cell_angle_alpha                80.053(3)
_cell_angle_beta                 81.737(3)
_cell_angle_gamma                75.392(3)
_cell_volume                     848.73(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3925
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2943
_reflns_number_gt                2471
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0867P)^2^+2.3203P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2943
_refine_ls_number_parameters     245
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0938
_refine_ls_wR_factor_ref         0.2389
_refine_ls_wR_factor_gt          0.2308
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.1650(8) 0.5041(9) 0.7998(8) 0.077(3) Uani 0.592(17) 1 d PD A 1
S2A S 0.3074(8) 0.0365(9) 0.6959(8) 0.081(3) Uani 0.592(17) 1 d PD A 1
N1A N 0.021(2) 0.308(4) 0.7175(18) 0.044(5) Uani 0.592(17) 1 d PDU A 1
H1NA H 0.0305 0.2169 0.6950 0.053 Uiso 0.592(17) 1 calc PR A 1
H1NB H -0.0735 0.3777 0.7180 0.053 Uiso 0.592(17) 1 calc PR A 1
N2A N 0.444(2) 0.233(4) 0.779(3) 0.047(6) Uani 0.592(17) 1 d PDU A 1
H2NA H 0.4358 0.3236 0.8022 0.056 Uiso 0.592(17) 1 calc PR A 1
H2NB H 0.5376 0.1623 0.7785 0.056 Uiso 0.592(17) 1 calc PR A 1
C1A C 0.1551(10) 0.3399(9) 0.7521(6) 0.033(3) Uani 0.592(17) 1 d PD A 1
C2A C 0.3093(10) 0.2035(9) 0.7452(6) 0.035(3) Uani 0.592(17) 1 d PD A 1
S1B S 0.1650(10) 0.5105(6) 0.7965(6) 0.038(3) Uani 0.408(17) 1 d PD A 2
S2B S 0.3031(10) 0.0308(6) 0.7017(7) 0.041(2) Uani 0.408(17) 1 d PD A 2
N1B N 0.434(3) 0.252(6) 0.789(4) 0.060(13) Uani 0.408(17) 1 d PDU A 2
H1NC H 0.4763 0.1555 0.7743 0.072 Uiso 0.408(17) 1 calc PR A 2
H1ND H 0.4943 0.3020 0.8146 0.072 Uiso 0.408(17) 1 calc PR A 2
N2B N 0.033(2) 0.287(6) 0.717(3) 0.060(13) Uani 0.408(17) 1 d PDU A 2
H2NC H -0.0088 0.3814 0.7348 0.072 Uiso 0.408(17) 1 calc PR A 2
H2ND H -0.0298 0.2379 0.6922 0.072 Uiso 0.408(17) 1 calc PR A 2
C1B C 0.2735(15) 0.3246(13) 0.7723(9) 0.037(4) Uani 0.408(17) 1 d PD A 2
C2B C 0.1956(16) 0.2139(12) 0.7279(9) 0.036(4) Uani 0.408(17) 1 d PD A 2
O1 O -0.3115(5) 0.3756(5) 0.5712(3) 0.0615(11) Uani 1 1 d . . .
C2 C -0.2971(8) 0.5373(7) 0.5425(5) 0.0597(15) Uani 1 1 d . . .
H2A H -0.3486 0.5859 0.4761 0.072 Uiso 1 1 calc R . .
H2B H -0.1798 0.5422 0.5310 0.072 Uiso 1 1 calc R . .
C3 C -0.3865(7) 0.6243(7) 0.6360(5) 0.0571(15) Uani 1 1 d . . .
H3A H -0.3958 0.7395 0.6162 0.068 Uiso 1 1 calc R . .
H3B H -0.4989 0.6060 0.6537 0.068 Uiso 1 1 calc R . .
O4 O -0.2942(4) 0.5656(5) 0.7267(3) 0.0561(10) Uani 1 1 d . . .
C5 C -0.3843(7) 0.6039(7) 0.8275(5) 0.0531(14) Uani 1 1 d . . .
H5A H -0.4998 0.5962 0.8297 0.064 Uiso 1 1 calc R . .
H5B H -0.3848 0.7136 0.8357 0.064 Uiso 1 1 calc R . .
C6 C -0.3018(7) 0.4884(7) 0.9174(5) 0.0520(14) Uani 1 1 d . . .
H6A H -0.1813 0.4789 0.9062 0.062 Uiso 1 1 calc R . .
H6B H -0.3441 0.5273 0.9866 0.062 Uiso 1 1 calc R . .
O7 O -0.3368(5) 0.3365(5) 0.9188(3) 0.0543(10) Uani 1 1 d . . .
C8 C -0.2275(7) 0.2078(7) 0.9785(5) 0.0548(14) Uani 1 1 d . . .
H8A H -0.2281 0.2319 1.0513 0.066 Uiso 1 1 calc R . .
H8B H -0.1136 0.1951 0.9429 0.066 Uiso 1 1 calc R . .
C9 C -0.2837(8) 0.0547(8) 0.9849(5) 0.0601(15) Uani 1 1 d . . .
H9A H -0.2094 -0.0318 1.0272 0.072 Uiso 1 1 calc R . .
H9B H -0.3959 0.0675 1.0231 0.072 Uiso 1 1 calc R . .
O10 O -0.2851(5) 0.0096(5) 0.8803(3) 0.0548(10) Uani 1 1 d . . .
C11 C -0.1281(7) -0.0784(6) 0.8360(5) 0.0527(14) Uani 1 1 d . . .
H11A H -0.1015 -0.1871 0.8752 0.063 Uiso 1 1 calc R . .
H11B H -0.0395 -0.0259 0.8416 0.063 Uiso 1 1 calc R . .
C12 C -0.1428(8) -0.0832(7) 0.7179(5) 0.0595(15) Uani 1 1 d . . .
H12A H -0.0466 -0.1594 0.6882 0.071 Uiso 1 1 calc R . .
H12B H -0.2438 -0.1174 0.7118 0.071 Uiso 1 1 calc R . .
O13 O -0.1498(5) 0.0728(5) 0.6598(3) 0.0595(11) Uani 1 1 d . . .
C14 C -0.2147(7) 0.0980(7) 0.5592(4) 0.0533(14) Uani 1 1 d . . .
H14A H -0.3290 0.0840 0.5701 0.064 Uiso 1 1 calc R . .
H14B H -0.1472 0.0206 0.5134 0.064 Uiso 1 1 calc R . .
C15 C -0.2119(8) 0.2661(7) 0.5060(5) 0.0596(15) Uani 1 1 d . . .
H15A H -0.0974 0.2796 0.4953 0.071 Uiso 1 1 calc R . .
H15B H -0.2537 0.2856 0.4352 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1A 0.032(4) 0.099(6) 0.107(6) -0.021(4) -0.016(3) -0.017(3)
S2A 0.038(4) 0.106(6) 0.107(6) -0.023(4) -0.020(3) -0.017(3)
N1A 0.035(10) 0.063(8) 0.039(9) 0.002(6) -0.020(7) -0.016(6)
N2A 0.024(9) 0.055(9) 0.060(9) -0.004(9) -0.008(6) -0.007(6)
C1A 0.033(6) 0.036(5) 0.030(4) -0.001(3) -0.006(3) -0.009(3)
C2A 0.024(5) 0.048(6) 0.029(4) 0.007(4) -0.003(3) -0.009(4)
S1B 0.050(5) 0.015(3) 0.055(4) -0.024(3) -0.012(3) -0.001(2)
S2B 0.052(5) 0.017(3) 0.058(4) -0.030(3) -0.012(3) 0.008(2)
N1B 0.025(15) 0.071(18) 0.09(2) -0.032(13) -0.030(13) -0.001(10)
N2B 0.011(11) 0.09(2) 0.08(2) -0.015(15) -0.006(10) -0.019(10)
C1B 0.036(9) 0.048(8) 0.027(6) 0.005(5) -0.008(5) -0.018(6)
C2B 0.034(9) 0.041(8) 0.033(6) 0.002(5) -0.008(5) -0.010(6)
O1 0.054(2) 0.060(2) 0.063(3) 0.000(2) 0.001(2) -0.0097(19)
C2 0.062(4) 0.062(4) 0.055(3) 0.010(3) -0.017(3) -0.020(3)
C3 0.045(3) 0.057(3) 0.068(4) 0.000(3) -0.020(3) -0.008(3)
O4 0.036(2) 0.075(3) 0.054(2) -0.0046(19) -0.0073(17) -0.0085(17)
C5 0.040(3) 0.052(3) 0.067(4) -0.012(3) 0.005(3) -0.014(2)
C6 0.039(3) 0.072(4) 0.054(3) -0.019(3) -0.002(2) -0.024(3)
O7 0.046(2) 0.060(2) 0.059(2) -0.0034(18) -0.0188(18) -0.0124(17)
C8 0.042(3) 0.076(4) 0.047(3) 0.003(3) -0.016(2) -0.015(3)
C9 0.054(3) 0.077(4) 0.047(3) 0.006(3) -0.012(3) -0.018(3)
O10 0.043(2) 0.064(2) 0.056(2) -0.0060(18) -0.0143(18) -0.0073(17)
C11 0.040(3) 0.046(3) 0.063(4) 0.006(3) -0.007(2) -0.001(2)
C12 0.065(4) 0.043(3) 0.068(4) -0.005(3) -0.010(3) -0.008(3)
O13 0.072(3) 0.057(2) 0.057(2) 0.0020(19) -0.025(2) -0.026(2)
C14 0.043(3) 0.072(4) 0.048(3) -0.016(3) -0.008(2) -0.011(3)
C15 0.059(4) 0.074(4) 0.042(3) -0.006(3) -0.010(3) -0.008(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C1A 1.657(9) . ?
S2A C2A 1.670(9) . ?
N1A C1A 1.352(16) . ?
N1A H1NA 0.8600 . ?
N1A H1NB 0.8600 . ?
N2A C2A 1.343(17) . ?
N2A H2NA 0.8600 . ?
N2A H2NB 0.8600 . ?
C1A C2A 1.506(11) . ?
S1B C1B 1.686(11) . ?
S2B C2B 1.670(10) . ?
N1B C1B 1.347(19) . ?
N1B H1NC 0.8600 . ?
N1B H1ND 0.8600 . ?
N2B C2B 1.351(18) . ?
N2B H2NC 0.8600 . ?
N2B H2ND 0.8600 . ?
C1B C2B 1.496(14) . ?
O1 C15 1.387(7) . ?
O1 C2 1.413(7) . ?
C2 C3 1.503(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.410(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.418(7) . ?
C5 C6 1.491(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.411(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.419(6) . ?
C8 C9 1.495(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.433(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 C11 1.419(6) . ?
C11 C12 1.510(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O13 1.409(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 C14 1.401(6) . ?
C14 C15 1.495(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A H1NA 120.0 . . ?
C1A N1A H1NB 120.0 . . ?
H1NA N1A H1NB 120.0 . . ?
C2A N2A H2NA 120.0 . . ?
C2A N2A H2NB 120.0 . . ?
H2NA N2A H2NB 120.0 . . ?
N1A C1A C2A 112.5(16) . . ?
N1A C1A S1A 128.2(15) . . ?
C2A C1A S1A 119.3(7) . . ?
N2A C2A C1A 113.3(17) . . ?
N2A C2A S2A 125.2(16) . . ?
C1A C2A S2A 121.4(7) . . ?
C1B N1B H1NC 120.0 . . ?
C1B N1B H1ND 120.0 . . ?
H1NC N1B H1ND 120.0 . . ?
C2B N2B H2NC 120.0 . . ?
C2B N2B H2ND 120.0 . . ?
H2NC N2B H2ND 120.0 . . ?
N1B C1B C2B 110(2) . . ?
N1B C1B S1B 128(2) . . ?
C2B C1B S1B 121.9(10) . . ?
N2B C2B C1B 109(2) . . ?
N2B C2B S2B 129(2) . . ?
C1B C2B S2B 122.3(10) . . ?
C15 O1 C2 116.1(5) . . ?
O1 C2 C3 106.3(5) . . ?
O1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
O4 C3 C2 108.7(4) . . ?
O4 C3 H3A 110.0 . . ?
C2 C3 H3A 110.0 . . ?
O4 C3 H3B 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C3 O4 C5 114.5(4) . . ?
O4 C5 C6 108.8(4) . . ?
O4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
O4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
O7 C6 C5 108.8(4) . . ?
O7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C6 O7 C8 113.4(4) . . ?
O7 C8 C9 109.7(4) . . ?
O7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
O7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O10 C9 C8 113.3(5) . . ?
O10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
O10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 O10 C9 114.7(4) . . ?
O10 C11 C12 107.3(4) . . ?
O10 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O10 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
O13 C12 C11 108.5(5) . . ?
O13 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
O13 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C14 O13 C12 114.0(4) . . ?
O13 C14 C15 108.2(4) . . ?
O13 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O13 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O1 C15 C14 109.5(5) . . ?
O1 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
O1 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 68.4(6) . . . . ?
C2 C3 O4 C5 -163.9(5) . . . . ?
C3 O4 C5 C6 158.9(5) . . . . ?
O4 C5 C6 O7 -73.1(5) . . . . ?
C5 C6 O7 C8 162.7(5) . . . . ?
C6 O7 C8 C9 174.5(5) . . . . ?
O7 C8 C9 O10 59.9(7) . . . . ?
C8 C9 O10 C11 84.5(6) . . . . ?
C9 O10 C11 C12 -167.7(5) . . . . ?
O10 C11 C12 O13 70.8(6) . . . . ?
C11 C12 O13 C14 -161.2(5) . . . . ?
C12 O13 C14 C15 -179.0(5) . . . . ?
O13 C14 C15 O1 -60.9(6) . . . . ?
C14 C15 O1 C2 168.5(5) . . . . ?
C15 O1 C2 C3 -168.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1NA O13 0.86 2.30 2.98(3) 136.4 .
N1A H1NB O4 0.86 2.12 2.97(3) 174.0 .
N1A H1NA S2A 0.86 2.42 2.90(3) 115.4 .
N2A H2NA O7 0.86 2.58 3.07(2) 117.3 1_655
N2A H2NB O10 0.86 2.12 2.85(2) 143.0 1_655
N2A H2NA S1A 0.86 2.38 2.86(3) 115.1 .
N1B H1NC O10 0.86 2.48 2.93(3) 112.9 1_655
N1B H1ND O7 0.86 2.15 2.96(4) 157.2 1_655
N2B H2NC S1B 0.86 2.31 2.83(4) 118.9 .
N2B H2NC O4 0.86 2.50 3.14(3) 132.2 .
N2B H2ND O13 0.86 2.05 2.89(4) 165.4 .
N1B H1NC S2B 0.86 2.35 2.85(5) 117.4 .

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.083

data_compound_2
_database_code_CSD               202645

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
cis-syn-cis (A) isomer (2,3,11,12-dicyclohexano-1,4,7,10,13,16-
hexaoxacyclooctadecane bis(ethanedithioamide) clathrate
;
_chemical_name_common            
;
cis-syn-cis (A) isomer (2,3,11,12-dicyclohexano-
1,4,7,10,13,16-hexaoxacyclooctadecane bis(ethanedithioamide) clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H36 O6 , 2(C2 H4 N2 S2)'
_chemical_formula_sum            'C24 H44 N4 O6 S4'
_chemical_formula_weight         612.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.72000(10)
_cell_length_b                   7.6550(2)
_cell_length_c                   18.3640(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.9810(6)
_cell_angle_gamma                90.0000
_cell_volume                     3189.09(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3649
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3649
_reflns_number_gt                3033
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+1.8229P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3649
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.41988(5) 0.13095(15) -0.15713(6) 0.0463(3) Uani 1 1 d . . .
C2 C 0.44538(8) 0.2626(3) -0.10327(11) 0.0572(5) Uani 1 1 d . . .
H2A H 0.4257 0.2664 -0.0639 0.069 Uiso 1 1 calc R . .
H2B H 0.4410 0.3757 -0.1281 0.069 Uiso 1 1 calc R . .
C3 C 0.50913(8) 0.2221(3) -0.06896(9) 0.0543(5) Uani 1 1 d . . .
H3A H 0.5265 0.3064 -0.0293 0.065 Uiso 1 1 calc R . .
H3B H 0.5133 0.1069 -0.0460 0.065 Uiso 1 1 calc R . .
O4 O 0.53914(5) 0.22753(14) -0.12577(5) 0.0399(3) Uani 1 1 d . . .
C5 C 0.60147(7) 0.2307(2) -0.09241(9) 0.0487(4) Uani 1 1 d . . .
H5A H 0.6136 0.1301 -0.0595 0.058 Uiso 1 1 calc R . .
H5B H 0.6126 0.3352 -0.0617 0.058 Uiso 1 1 calc R . .
C6 C 0.63187(8) 0.2283(2) -0.15329(10) 0.0492(4) Uani 1 1 d . . .
H6A H 0.6142 0.3142 -0.1921 0.059 Uiso 1 1 calc R . .
H6B H 0.6732 0.2572 -0.1317 0.059 Uiso 1 1 calc R . .
O7 O 0.62617(5) 0.05872(15) -0.18600(6) 0.0418(3) Uani 1 1 d . . .
C8 C 0.65893(7) 0.0292(2) -0.23935(9) 0.0468(4) Uani 1 1 d . . .
H8A H 0.7008 0.0472 -0.2128 0.056 Uiso 1 1 calc R . .
C9 C 0.64196(7) 0.1507(3) -0.30802(9) 0.0512(4) Uani 1 1 d . . .
H9A H 0.6506 0.2717 -0.2911 0.061 Uiso 1 1 calc R . .
C10 C 0.67771(9) 0.1018(4) -0.36250(12) 0.0725(7) Uani 1 1 d . . .
H10A H 0.6658 0.1759 -0.4072 0.087 Uiso 1 1 calc R . .
H10B H 0.7192 0.1229 -0.3376 0.087 Uiso 1 1 calc R . .
C11 C 0.66926(10) -0.0871(4) -0.38688(12) 0.0776(7) Uani 1 1 d . . .
H11A H 0.6937 -0.1138 -0.4196 0.093 Uiso 1 1 calc R . .
H11B H 0.6284 -0.1065 -0.4158 0.093 Uiso 1 1 calc R . .
C12 C 0.68559(11) -0.2072(4) -0.31799(13) 0.0775(7) Uani 1 1 d . . .
H12A H 0.7274 -0.1968 -0.2920 0.093 Uiso 1 1 calc R . .
H12B H 0.6776 -0.3274 -0.3345 0.093 Uiso 1 1 calc R . .
C13 C 0.65029(9) -0.1602(3) -0.26319(10) 0.0561(5) Uani 1 1 d . . .
H13A H 0.6088 -0.1819 -0.2877 0.067 Uiso 1 1 calc R . .
H13B H 0.6627 -0.2341 -0.2184 0.067 Uiso 1 1 calc R . .
S1G S 0.77332(2) 0.00340(7) -0.03319(3) 0.06652(18) Uani 1 1 d . . .
C1G C 0.73590(8) -0.1753(2) -0.02647(9) 0.0458(4) Uani 1 1 d . . .
N1G N 0.68022(7) -0.2031(3) -0.06457(9) 0.0523(4) Uani 1 1 d . . .
H1NA H 0.6632(10) -0.301(3) -0.0550(13) 0.074(7) Uiso 1 1 d . . .
H1NB H 0.6607(10) -0.124(3) -0.0967(13) 0.069(6) Uiso 1 1 d . . .
S2G S 0.53055(2) -0.28934(6) -0.12649(2) 0.05210(14) Uani 1 1 d . . .
C3G C 0.50763(13) -0.3539(4) -0.21748(16) 0.0362(6) Uani 0.50 1 d P . .
C2G C 0.49188(12) -0.2211(4) -0.28185(16) 0.0347(6) Uani 0.50 1 d P . .
N3G N 0.5000 -0.5178(3) -0.2500 0.0596(6) Uani 1 2 d S . .
H3N H 0.5075(12) -0.579(3) -0.2108(14) 0.096(9) Uiso 1 1 d . . .
N2G N 0.5000 -0.0594(3) -0.2500 0.0535(6) Uani 1 2 d S . .
H2N H 0.5087(13) -0.007(3) -0.2118(14) 0.093(9) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0414(6) 0.0569(7) 0.0394(6) -0.0126(5) 0.0098(5) -0.0015(5)
C2 0.0588(11) 0.0676(12) 0.0511(10) -0.0244(9) 0.0254(9) -0.0106(9)
C3 0.0598(11) 0.0727(12) 0.0314(8) -0.0125(8) 0.0149(7) -0.0169(9)
O4 0.0440(6) 0.0449(6) 0.0290(5) -0.0039(4) 0.0077(4) -0.0050(5)
C5 0.0458(9) 0.0568(10) 0.0369(8) -0.0101(7) 0.0017(7) -0.0028(8)
C6 0.0437(9) 0.0520(10) 0.0493(9) -0.0028(8) 0.0097(7) -0.0070(7)
O7 0.0425(6) 0.0510(6) 0.0321(5) 0.0004(5) 0.0112(4) -0.0034(5)
C8 0.0342(8) 0.0725(12) 0.0333(8) 0.0043(8) 0.0095(6) 0.0002(7)
C9 0.0442(9) 0.0701(12) 0.0396(9) 0.0054(8) 0.0127(7) -0.0106(8)
C10 0.0476(11) 0.128(2) 0.0464(11) 0.0178(12) 0.0207(9) -0.0025(12)
C11 0.0660(13) 0.127(2) 0.0455(11) -0.0055(12) 0.0259(10) 0.0175(13)
C12 0.0744(14) 0.1054(18) 0.0564(12) -0.0044(12) 0.0248(11) 0.0308(13)
C13 0.0579(11) 0.0669(12) 0.0444(10) 0.0037(8) 0.0163(8) 0.0165(9)
S1G 0.0623(3) 0.0547(3) 0.0705(3) 0.0153(2) 0.0004(2) -0.0149(2)
C1G 0.0505(9) 0.0521(10) 0.0337(8) -0.0032(7) 0.0107(7) -0.0007(7)
N1G 0.0439(8) 0.0628(10) 0.0421(8) 0.0078(7) 0.0000(6) -0.0027(8)
S2G 0.0706(3) 0.0466(2) 0.0319(2) -0.00015(17) 0.00368(19) -0.0043(2)
C3G 0.0334(15) 0.0375(18) 0.0358(13) 0.0019(12) 0.0072(12) 0.0002(12)
C2G 0.0301(14) 0.0359(17) 0.0366(13) 0.0035(12) 0.0073(12) 0.0017(12)
N3G 0.0696(16) 0.0310(11) 0.0747(18) 0.000 0.0154(13) 0.000
N2G 0.0505(13) 0.0327(11) 0.0749(18) 0.000 0.0148(12) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.418(2) . ?
O1 C9 1.427(2) 2_654 ?
C2 C3 1.491(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.4248(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.4257(19) . ?
C5 C6 1.497(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.420(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.4352(19) . ?
C8 C13 1.512(3) . ?
C8 C9 1.523(2) . ?
C8 H8A 0.9800 . ?
C9 O1 1.427(2) 2_654 ?
C9 C10 1.535(3) . ?
C9 H9A 0.9800 . ?
C10 C11 1.509(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.528(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
S1G C1G 1.6551(18) . ?
C1G N1G 1.319(2) . ?
C1G C1G 1.523(3) 7_645 ?
N1G H1NA 0.89(2) . ?
N1G H1NB 0.88(2) . ?
S2G C3G 1.674(3) . ?
S2G C2G 1.693(3) 2_654 ?
C3G C2G 1.017(4) 2_654 ?
C3G C3G 1.142(6) 2_654 ?
C3G N3G 1.379(4) 2_654 ?
C3G N3G 1.379(4) . ?
C3G C2G 1.521(4) . ?
C2G C3G 1.017(4) 2_654 ?
C2G C2G 1.120(6) 2_654 ?
C2G N2G 1.359(4) . ?
C2G N2G 1.359(4) 2_654 ?
C2G S2G 1.693(3) 2_654 ?
N3G N3G 0.0000 2_654 ?
N3G C3G 1.379(4) 2_654 ?
N3G H3N 0.83(2) . ?
N2G N2G 0.0000 2_654 ?
N2G C2G 1.359(4) 2_654 ?
N2G H2N 0.78(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C9 114.27(13) . 2_654 ?
O1 C2 C3 108.68(15) . . ?
O1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
O1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.3 . . ?
O4 C3 C2 110.26(14) . . ?
O4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
O4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C3 O4 C5 111.29(12) . . ?
O4 C5 C6 110.14(13) . . ?
O4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
O4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O7 C6 C5 108.66(14) . . ?
O7 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O7 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
C6 O7 C8 115.39(13) . . ?
O7 C8 C13 107.09(13) . . ?
O7 C8 C9 113.85(14) . . ?
C13 C8 C9 111.42(14) . . ?
O7 C8 H8A 108.1 . . ?
C13 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
O1 C9 C8 107.18(13) 2_654 . ?
O1 C9 C10 111.90(15) 2_654 . ?
C8 C9 C10 109.14(17) . . ?
O1 C9 H9A 109.5 2_654 . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C11 C10 C9 112.11(17) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 110.69(18) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 110.48(17) . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C8 C13 C12 111.26(18) . . ?
C8 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C8 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
N1G C1G C1G 113.77(19) . 7_645 ?
N1G C1G S1G 124.70(14) . . ?
C1G C1G S1G 121.52(17) 7_645 . ?
C1G N1G H1NA 118.1(14) . . ?
C1G N1G H1NB 119.7(14) . . ?
H1NA N1G H1NB 122(2) . . ?
C3G S2G C2G 35.15(13) . 2_654 ?
C2G C3G C3G 89.4(2) 2_654 2_654 ?
C2G C3G N3G 154.9(3) 2_654 2_654 ?
C3G C3G N3G 65.52(13) 2_654 2_654 ?
C2G C3G N3G 154.9(3) 2_654 . ?
C3G C3G N3G 65.52(13) 2_654 . ?
N3G C3G N3G 0.00(8) 2_654 . ?
C2G C3G C2G 47.4(3) 2_654 . ?
C3G C3G C2G 41.96(15) 2_654 . ?
N3G C3G C2G 107.5(2) 2_654 . ?
N3G C3G C2G 107.5(2) . . ?
C2G C3G S2G 73.5(2) 2_654 . ?
C3G C3G S2G 162.78(11) 2_654 . ?
N3G C3G S2G 131.6(2) 2_654 . ?
N3G C3G S2G 131.6(2) . . ?
C2G C3G S2G 120.9(2) . . ?
C3G C2G C2G 90.6(2) 2_654 2_654 ?
C3G C2G N2G 156.3(3) 2_654 . ?
C2G C2G N2G 65.67(13) 2_654 . ?
C3G C2G N2G 156.3(3) 2_654 2_654 ?
C2G C2G N2G 65.67(13) 2_654 2_654 ?
N2G C2G N2G 0.00(8) . 2_654 ?
C3G C2G C3G 48.7(3) 2_654 . ?
C2G C2G C3G 41.96(15) 2_654 . ?
N2G C2G C3G 107.6(2) . . ?
N2G C2G C3G 107.6(2) 2_654 . ?
C3G C2G S2G 71.4(2) 2_654 2_654 ?
C2G C2G S2G 162.01(11) 2_654 2_654 ?
N2G C2G S2G 132.3(2) . 2_654 ?
N2G C2G S2G 132.3(2) 2_654 2_654 ?
C3G C2G S2G 120.1(2) . 2_654 ?
N3G N3G C3G 0(10) 2_654 2_654 ?
N3G N3G C3G 0(10) 2_654 . ?
C3G N3G C3G 49.0(3) 2_654 . ?
N3G N3G H3N 0(10) 2_654 . ?
C3G N3G H3N 148.7(19) 2_654 . ?
C3G N3G H3N 99.9(18) . . ?
N2G N2G C2G 0(10) 2_654 . ?
N2G N2G C2G 0(10) 2_654 2_654 ?
C2G N2G C2G 48.7(3) . 2_654 ?
N2G N2G H2N 0(10) 2_654 . ?
C2G N2G H2N 145(2) . . ?
C2G N2G H2N 96.4(19) 2_654 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 63.4(2) . . . . ?
C2 C3 O4 C5 166.14(15) . . . . ?
C3 O4 C5 C6 177.46(15) . . . . ?
O4 C5 C6 O7 -72.59(17) . . . . ?
C5 C6 O7 C8 -173.03(13) . . . . ?
C6 O7 C8 C9 -60.11(18) . . . . ?
O7 C8 C9 O1 -56.11(19) . . . 2_654 ?
C8 C9 O1 C2 166.18(15) . . 2_654 2_654 ?
C9 O1 C2 C3 177.52(14) . 2_654 2_654 2_654 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1G H1NB O7 0.88(2) 2.13(2) 2.994(2) 168.7(19) .
N1G H1NA S1G 0.89(2) 2.42(2) 2.9271(19) 116.2(17) 7_645
N2G H2N O4 0.78(2) 2.36(2) 3.1069(18) 160(3) .
N2G H2N S2G 0.78(2) 2.63(3) 2.7945(15) 94(2) .
N3G H3N O4 0.83(2) 2.12(3) 2.9377(18) 166(3) 1_545

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.040

data_compound_3
_database_code_CSD               202646

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
cis-anti-cis (B) isomer (2,3,11,12-dicyclohexano-1,4,7,10,13,16-
hexaoxacyclooctadecane bis(ethanedithioamide) clathrate
;
_chemical_name_common            
;
cis-anti-cis (B) isomer (2,3,11,12-dicyclohexano-
1,4,7,10,13,16-hexaoxacyclooctadecane bis(ethanedithioamide) clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H36 O6 , 2(C2 H4 N2 S2)'
_chemical_formula_sum            'C24 H44 N4 O6 S4'
_chemical_formula_weight         612.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.654(3)
_cell_length_b                   7.5700(15)
_cell_length_c                   17.129(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.14(3)
_cell_angle_gamma                90.00
_cell_volume                     1576.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3592
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3592
_reflns_number_gt                3212
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+0.4780P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3592
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1G S 0.00826(4) 0.25974(6) 0.05297(4) 0.05658(16) Uani 1 1 d . . .
N1G N 0.13293(12) 0.0540(2) -0.00725(10) 0.0472(4) Uani 1 1 d . . .
H1G1 H 0.1413(18) -0.045(3) -0.0292(14) 0.057 Uiso 1 1 d . . .
H2G1 H 0.1816(18) 0.138(3) 0.0016(13) 0.057 Uiso 1 1 d . . .
C1G C 0.03980(12) 0.0778(2) 0.01098(9) 0.0376(3) Uani 1 1 d . . .
N2G N 0.50793(12) 0.23124(18) 0.01093(9) 0.0393(3) Uani 1 1 d . . .
H1G2 H 0.5428(17) 0.313(3) 0.0389(12) 0.047 Uiso 1 1 d . . .
H2G2 H 0.4482(19) 0.254(2) -0.0225(14) 0.047 Uiso 1 1 d . . .
S2G S 0.65622(3) 0.00749(5) 0.09381(3) 0.04542(14) Uani 1 1 d . . .
C2G C 0.53967(11) 0.06823(19) 0.02530(9) 0.0309(3) Uani 1 1 d . . .
O1 O 0.69221(8) 0.66789(15) -0.05982(6) 0.0369(2) Uani 1 1 d . . .
C2 C 0.72716(14) 0.4954(2) -0.03128(11) 0.0440(4) Uani 1 1 d . . .
H2A H 0.7902 0.4609 -0.0495 0.053 Uiso 1 1 calc R . .
H2B H 0.6684 0.4112 -0.0526 0.053 Uiso 1 1 calc R . .
C3 C 0.75742(13) 0.4960(2) 0.05977(11) 0.0437(4) Uani 1 1 d . . .
H3A H 0.7918 0.3845 0.0804 0.052 Uiso 1 1 calc R . .
H3B H 0.8099 0.5898 0.0806 0.052 Uiso 1 1 calc R . .
O4 O 0.66171(8) 0.52186(14) 0.08679(6) 0.0346(2) Uani 1 1 d . . .
C5 C 0.68728(14) 0.5246(3) 0.17295(10) 0.0464(4) Uani 1 1 d . . .
H5A H 0.7416 0.6155 0.1944 0.056 Uiso 1 1 calc R . .
H5B H 0.7182 0.4117 0.1947 0.056 Uiso 1 1 calc R . .
C6 C 0.58569(15) 0.5606(3) 0.19848(11) 0.0494(4) Uani 1 1 d . . .
H6A H 0.6041 0.5720 0.2571 0.059 Uiso 1 1 calc R . .
H6B H 0.5523 0.6704 0.1745 0.059 Uiso 1 1 calc R . .
O7 O 0.51109(9) 0.41906(15) 0.17240(7) 0.0407(3) Uani 1 1 d . . .
C8 C 0.41260(13) 0.4332(3) 0.19748(10) 0.0445(4) Uani 1 1 d . . .
H8 H 0.3843 0.5542 0.1884 0.053 Uiso 1 1 calc R . .
C9 C 0.32832(12) 0.3057(2) 0.14566(9) 0.0408(4) Uani 1 1 d . . .
H9 H 0.2588 0.3220 0.1594 0.049 Uiso 1 1 calc R . .
C10 C 0.36358(16) 0.1155(3) 0.16271(10) 0.0507(4) Uani 1 1 d . . .
H10A H 0.4302 0.0950 0.1466 0.061 Uiso 1 1 calc R . .
H10B H 0.3067 0.0384 0.1305 0.061 Uiso 1 1 calc R . .
C11 C 0.38450(19) 0.0697(4) 0.25278(13) 0.0683(6) Uani 1 1 d . . .
H11A H 0.3162 0.0776 0.2678 0.082 Uiso 1 1 calc R . .
H11B H 0.4115 -0.0505 0.2623 0.082 Uiso 1 1 calc R . .
C12 C 0.46822(18) 0.1958(4) 0.30456(12) 0.0701(7) Uani 1 1 d . . .
H12A H 0.4774 0.1702 0.3616 0.084 Uiso 1 1 calc R . .
H12B H 0.5387 0.1785 0.2936 0.084 Uiso 1 1 calc R . .
C13 C 0.43270(16) 0.3849(4) 0.28743(11) 0.0642(6) Uani 1 1 d . . .
H13A H 0.4890 0.4620 0.3202 0.077 Uiso 1 1 calc R . .
H13B H 0.3656 0.4044 0.3031 0.077 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1G 0.0480(3) 0.0440(3) 0.0784(4) -0.0119(2) 0.0187(2) 0.00067(19)
N1G 0.0317(7) 0.0562(9) 0.0527(9) -0.0068(7) 0.0104(6) -0.0046(6)
C1G 0.0319(7) 0.0428(9) 0.0337(7) 0.0049(6) 0.0018(6) 0.0029(6)
N2G 0.0356(7) 0.0300(7) 0.0456(8) -0.0067(5) 0.0001(6) -0.0010(5)
S2G 0.0346(2) 0.0388(2) 0.0514(3) -0.00611(17) -0.00704(18) 0.00231(15)
C2G 0.0276(6) 0.0320(7) 0.0333(7) -0.0051(6) 0.0089(5) -0.0014(6)
O1 0.0336(5) 0.0446(6) 0.0293(5) -0.0008(4) 0.0038(4) 0.0011(5)
C2 0.0391(8) 0.0453(9) 0.0479(9) 0.0005(7) 0.0125(7) 0.0049(7)
C3 0.0291(7) 0.0518(10) 0.0464(9) 0.0101(7) 0.0043(7) 0.0034(7)
O4 0.0285(5) 0.0357(5) 0.0340(5) 0.0002(4) -0.0001(4) -0.0017(4)
C5 0.0383(8) 0.0583(10) 0.0343(8) -0.0010(7) -0.0038(6) -0.0138(7)
C6 0.0516(10) 0.0552(10) 0.0390(9) -0.0152(8) 0.0086(7) -0.0142(8)
O7 0.0340(5) 0.0489(7) 0.0384(6) -0.0111(5) 0.0087(4) -0.0062(5)
C8 0.0353(8) 0.0616(11) 0.0348(8) -0.0115(7) 0.0068(6) 0.0025(7)
C9 0.0288(7) 0.0632(10) 0.0298(7) -0.0017(7) 0.0070(6) -0.0006(7)
C10 0.0489(10) 0.0617(11) 0.0377(9) 0.0086(8) 0.0057(7) -0.0096(8)
C11 0.0615(12) 0.0948(17) 0.0446(10) 0.0234(11) 0.0081(9) -0.0087(12)
C12 0.0531(11) 0.119(2) 0.0324(9) 0.0137(11) 0.0033(8) -0.0014(12)
C13 0.0445(10) 0.1146(19) 0.0331(9) -0.0171(10) 0.0103(7) -0.0064(11)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1G C1G 1.6532(17) . ?
N1G C1G 1.313(2) . ?
N1G H1G1 0.86(2) . ?
N1G H2G1 0.87(2) . ?
C1G C1G 1.528(3) 3 ?
N2G C2G 1.300(2) . ?
N2G H1G2 0.83(2) . ?
N2G H2G2 0.83(2) . ?
S2G C2G 1.6736(16) . ?
C2G C2G 1.531(3) 3_655 ?
O1 C2 1.421(2) . ?
O1 C9 1.4342(18) 3_665 ?
C2 C3 1.499(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.425(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.420(2) . ?
C5 C6 1.494(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.416(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.431(2) . ?
C8 C9 1.527(2) . ?
C8 C13 1.535(3) . ?
C8 H8 0.9800 . ?
C9 O1 1.4342(18) 3_665 ?
C9 C10 1.512(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.531(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.516(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1G N1G H1G1 117.0(15) . . ?
C1G N1G H2G1 120.0(14) . . ?
H1G1 N1G H2G1 123(2) . . ?
N1G C1G C1G 114.19(18) . 3 ?
N1G C1G S1G 123.99(14) . . ?
C1G C1G S1G 121.81(16) 3 . ?
C2G N2G H1G2 120.8(14) . . ?
C2G N2G H2G2 120.0(13) . . ?
H1G2 N2G H2G2 118.8(19) . . ?
N2G C2G C2G 114.45(16) . 3_655 ?
N2G C2G S2G 124.01(11) . . ?
C2G C2G S2G 121.54(14) 3_655 . ?
C2 O1 C9 115.53(13) . 3_665 ?
O1 C2 C3 108.67(14) . . ?
O1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
O1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.3 . . ?
O4 C3 C2 110.12(13) . . ?
O4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
O4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C5 O4 C3 111.76(12) . . ?
O4 C5 C6 109.93(14) . . ?
O4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
O4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O7 C6 C5 108.78(14) . . ?
O7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C6 O7 C8 114.11(13) . . ?
O7 C8 C9 107.71(12) . . ?
O7 C8 C13 111.63(14) . . ?
C9 C8 C13 109.08(16) . . ?
O7 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C13 C8 H8 109.5 . . ?
O1 C9 C10 106.87(13) 3_665 . ?
O1 C9 C8 113.96(14) 3_665 . ?
C10 C9 C8 111.66(14) . . ?
O1 C9 H9 108.1 3_665 . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C9 C10 C11 111.66(18) . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 110.13(17) . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.27(18) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C8 112.32(17) . . ?
C12 C13 H13A 109.1 . . ?
C8 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C8 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 67.81(17) . . . . ?
C2 C3 O4 C5 -179.54(14) . . . . ?
C3 O4 C5 C6 177.29(14) . . . . ?
O4 C5 C6 O7 64.16(19) . . . . ?
C5 C6 O7 C8 176.54(14) . . . . ?
C6 O7 C8 C9 163.68(15) . . . . ?
O7 C8 C9 O1 -55.25(18) . . . 3_665 ?
C8 C9 O1 C2 -56.44(18) . . 3_665 3_665 ?
C9 O1 C2 C3 -173.47(12) . 3_665 3_665 3_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1G H1G1 S1G 0.86(2) 2.44(2) 2.9444(19) 118.0(18) 3
N1G H2G1 O1 0.87(2) 2.20(2) 3.039(2) 163.8(19) 3_665
N2G H1G2 O4 0.83(2) 2.18(2) 2.9848(18) 163.3(18) .
N2G H1G2 O7 0.83(2) 2.56(2) 3.1002(19) 124.0(16) .
N2G H2G2 O4 0.83(2) 2.28(2) 2.9841(19) 143.5(18) 3_665
N2G H2G2 S2G 0.83(2) 2.50(2) 2.9541(16) 115.6(15) 3_655

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048

data_compound_4
_database_code_CSD               202647

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4,7,10,13,16-hexaoxacyclooctadecane
N,N'-(thiocarbamoyl)hydrazine clathrate
;
_chemical_name_common            
;1,4,7,10,13,16-hexaoxacyclooctadecane N,N'-
(thiocarbamoyl)hydrazine clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6 , C2 H6 N4 S2'
_chemical_formula_sum            'C14 H30 N4 O6 S2'
_chemical_formula_weight         414.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.196(3)
_cell_length_b                   7.187(2)
_cell_length_c                   19.552(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.18(2)
_cell_angle_gamma                90.00
_cell_volume                     1993.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4532
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4532
_reflns_number_gt                3860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.8022P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4532
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.77624(7) 1.02704(13) -0.24061(5) 0.0183(2) Uani 1 1 d . . .
C2 C 0.86221(10) 1.0074(2) -0.27563(7) 0.0210(3) Uani 1 1 d . . .
H2A H 0.8775 1.1234 -0.2981 0.025 Uiso 1 1 calc R . .
H2B H 0.8555 0.9111 -0.3102 0.025 Uiso 1 1 calc R . .
C3 C 0.93888(10) 0.95679(19) -0.22449(7) 0.0218(3) Uani 1 1 d . . .
H3A H 0.9248 0.8386 -0.2032 0.026 Uiso 1 1 calc R . .
H3B H 0.9984 0.9453 -0.2469 0.026 Uiso 1 1 calc R . .
O4 O 0.94465(7) 1.10036(13) -0.17416(5) 0.0205(2) Uani 1 1 d . . .
C5 C 1.01158(10) 1.0593(2) -0.12033(7) 0.0228(3) Uani 1 1 d . . .
H5A H 1.0746 1.0571 -0.1378 0.027 Uiso 1 1 calc R . .
H5B H 0.9985 0.9382 -0.1010 0.027 Uiso 1 1 calc R . .
C6 C 1.00481(10) 1.2065(2) -0.06668(8) 0.0237(3) Uani 1 1 d . . .
H6A H 1.0572 1.1955 -0.0336 0.028 Uiso 1 1 calc R . .
H6B H 1.0072 1.3288 -0.0875 0.028 Uiso 1 1 calc R . .
O7 O 0.91779(7) 1.18341(13) -0.03344(5) 0.0203(2) Uani 1 1 d . . .
C8 C 0.89723(10) 1.33613(18) 0.00946(7) 0.0199(3) Uani 1 1 d . . .
H8A H 0.8925 1.4494 -0.0174 0.024 Uiso 1 1 calc R . .
H8B H 0.9474 1.3519 0.0440 0.024 Uiso 1 1 calc R . .
C9 C 0.80596(10) 1.29995(19) 0.04299(7) 0.0200(3) Uani 1 1 d . . .
H9A H 0.8108 1.1876 0.0704 0.024 Uiso 1 1 calc R . .
H9B H 0.7912 1.4029 0.0728 0.024 Uiso 1 1 calc R . .
O10 O 0.73362(7) 1.27935(13) -0.00898(5) 0.0180(2) Uani 1 1 d . . .
C11 C 0.64288(10) 1.26601(19) 0.01956(7) 0.0212(3) Uani 1 1 d . . .
H11A H 0.6216 1.3885 0.0330 0.025 Uiso 1 1 calc R . .
H11B H 0.6463 1.1875 0.0599 0.025 Uiso 1 1 calc R . .
C12 C 0.57498(10) 1.18500(18) -0.03261(7) 0.0211(3) Uani 1 1 d . . .
H12A H 0.5945 1.0600 -0.0443 0.025 Uiso 1 1 calc R . .
H12B H 0.5127 1.1779 -0.0140 0.025 Uiso 1 1 calc R . .
O13 O 0.57206(7) 1.29893(12) -0.09242(5) 0.0199(2) Uani 1 1 d . . .
C14 C 0.49799(10) 1.24699(19) -0.13997(8) 0.0224(3) Uani 1 1 d . . .
H14A H 0.4979 1.3331 -0.1782 0.027 Uiso 1 1 calc R . .
H14B H 0.4384 1.2617 -0.1178 0.027 Uiso 1 1 calc R . .
C15 C 0.50279(10) 1.04979(19) -0.16810(8) 0.0223(3) Uani 1 1 d . . .
H15A H 0.4920 0.9637 -0.1310 0.027 Uiso 1 1 calc R . .
H15B H 0.4516 1.0338 -0.2019 0.027 Uiso 1 1 calc R . .
O16 O 0.58883(7) 0.99911(12) -0.19880(5) 0.0197(2) Uani 1 1 d . . .
C17 C 0.61557(10) 1.12552(18) -0.25063(7) 0.0189(3) Uani 1 1 d . . .
H17A H 0.6325 1.2444 -0.2301 0.023 Uiso 1 1 calc R . .
H17B H 0.5629 1.1454 -0.2828 0.023 Uiso 1 1 calc R . .
C18 C 0.69767(10) 1.04959(19) -0.28759(7) 0.0197(3) Uani 1 1 d . . .
H18A H 0.6810 0.9306 -0.3081 0.024 Uiso 1 1 calc R . .
H18B H 0.7141 1.1342 -0.3239 0.024 Uiso 1 1 calc R . .
S1G S 0.72315(3) 0.77592(5) 0.028017(17) 0.02041(9) Uani 1 1 d . . .
S2G S 0.76431(3) 0.53786(5) -0.278494(17) 0.02138(9) Uani 1 1 d . . .
N1G N 0.78149(9) 0.89905(16) -0.09144(7) 0.0207(3) Uani 1 1 d . . .
H1N1 H 0.8136(13) 0.984(3) -0.0682(9) 0.037(5) Uiso 1 1 d . . .
H2N1 H 0.7755(12) 0.912(2) -0.1345(10) 0.032(5) Uiso 1 1 d . . .
N2G N 0.67356(9) 0.66179(16) -0.09644(6) 0.0179(2) Uani 1 1 d . . .
H1N2 H 0.6449(11) 0.579(2) -0.0790(8) 0.021(4) Uiso 1 1 d . . .
N3G N 0.68304(9) 0.64495(16) -0.16660(6) 0.0180(2) Uani 1 1 d . . .
H1N3 H 0.6619(11) 0.727(2) -0.1891(8) 0.019(4) Uiso 1 1 d . . .
N4G N 0.78820(9) 0.40527(17) -0.15151(7) 0.0215(3) Uani 1 1 d . . .
H1N4 H 0.8224(13) 0.325(2) -0.1677(9) 0.028(5) Uiso 1 1 d . . .
H2N4 H 0.7683(13) 0.389(2) -0.1101(10) 0.034(5) Uiso 1 1 d . . .
C1G C 0.72800(9) 0.78126(17) -0.05800(7) 0.0159(3) Uani 1 1 d . . .
C2G C 0.74635(9) 0.52654(17) -0.19407(7) 0.0162(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0173(5) 0.0220(5) 0.0157(5) 0.0001(4) 0.0023(4) 0.0002(4)
C2 0.0217(8) 0.0230(7) 0.0186(7) -0.0023(5) 0.0059(6) -0.0014(6)
C3 0.0207(7) 0.0210(7) 0.0243(7) -0.0041(5) 0.0057(6) 0.0026(6)
O4 0.0201(5) 0.0205(5) 0.0208(5) -0.0021(4) -0.0010(4) 0.0040(4)
C5 0.0138(7) 0.0289(7) 0.0256(8) 0.0009(6) 0.0005(6) 0.0035(6)
C6 0.0152(7) 0.0301(8) 0.0258(8) -0.0002(6) 0.0013(6) -0.0050(6)
O7 0.0172(5) 0.0205(5) 0.0235(5) -0.0044(4) 0.0033(4) -0.0038(4)
C8 0.0222(7) 0.0172(6) 0.0202(7) -0.0025(5) -0.0025(6) -0.0025(5)
C9 0.0242(8) 0.0203(7) 0.0154(7) -0.0008(5) -0.0007(6) 0.0004(6)
O10 0.0167(5) 0.0227(5) 0.0148(5) 0.0010(4) 0.0018(4) -0.0018(4)
C11 0.0208(7) 0.0216(7) 0.0218(7) 0.0031(5) 0.0082(6) 0.0001(6)
C12 0.0188(7) 0.0176(6) 0.0273(8) 0.0063(5) 0.0048(6) -0.0012(5)
O13 0.0196(5) 0.0167(5) 0.0235(5) 0.0051(4) 0.0010(4) -0.0024(4)
C14 0.0144(7) 0.0249(7) 0.0279(8) 0.0031(6) 0.0001(6) 0.0030(6)
C15 0.0134(7) 0.0247(7) 0.0290(8) 0.0007(6) 0.0012(6) -0.0034(5)
O16 0.0180(5) 0.0171(4) 0.0241(5) 0.0046(4) 0.0029(4) 0.0006(4)
C17 0.0204(7) 0.0154(6) 0.0207(7) 0.0039(5) -0.0025(6) -0.0020(5)
C18 0.0214(7) 0.0207(7) 0.0168(7) 0.0002(5) -0.0024(5) -0.0025(5)
S1G 0.0265(2) 0.01881(17) 0.01617(18) 0.00096(12) 0.00387(14) 0.00028(13)
S2G 0.0278(2) 0.01880(17) 0.01795(18) 0.00037(13) 0.00630(14) -0.00195(14)
N1G 0.0247(7) 0.0205(6) 0.0171(6) -0.0006(5) 0.0034(5) -0.0077(5)
N2G 0.0230(6) 0.0156(5) 0.0155(6) 0.0010(4) 0.0057(5) -0.0052(5)
N3G 0.0239(7) 0.0153(5) 0.0148(6) 0.0018(4) 0.0012(5) 0.0017(5)
N4G 0.0249(7) 0.0194(6) 0.0205(7) 0.0004(5) 0.0034(5) 0.0051(5)
C1G 0.0159(7) 0.0127(6) 0.0194(7) 0.0000(5) 0.0033(5) 0.0033(5)
C2G 0.0159(7) 0.0129(6) 0.0199(7) -0.0010(5) 0.0002(5) -0.0044(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.4270(17) . ?
O1 C2 1.4289(16) . ?
C2 C3 1.495(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.4261(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.4218(17) . ?
C5 C6 1.496(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.4271(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.4185(16) . ?
C8 C9 1.4969(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.4248(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 C11 1.4265(16) . ?
C11 C12 1.495(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O13 1.4268(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 C14 1.4267(17) . ?
C14 C15 1.523(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O16 1.4285(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O16 C17 1.4232(16) . ?
C17 C18 1.4974(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
S1G C1G 1.6863(14) . ?
S2G C2G 1.6817(14) . ?
N1G C1G 1.3260(17) . ?
N1G H1N1 0.876(19) . ?
N1G H2N1 0.847(18) . ?
N2G C1G 1.3620(17) . ?
N2G N3G 1.3888(16) . ?
N2G H1N2 0.802(16) . ?
N3G C2G 1.3628(17) . ?
N3G H1N3 0.790(16) . ?
N4G C2G 1.3295(18) . ?
N4G H1N4 0.824(18) . ?
N4G H2N4 0.876(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C2 111.32(10) . . ?
O1 C2 C3 108.48(11) . . ?
O1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
O1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O4 C3 C2 107.86(11) . . ?
O4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 O4 C3 112.32(10) . . ?
O4 C5 C6 108.26(11) . . ?
O4 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
O4 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
O7 C6 C5 108.48(11) . . ?
O7 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O7 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C8 O7 C6 112.36(10) . . ?
O7 C8 C9 109.00(11) . . ?
O7 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O7 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O10 C9 C8 108.54(11) . . ?
O10 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O10 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C9 O10 C11 111.41(10) . . ?
O10 C11 C12 109.13(11) . . ?
O10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
O13 C12 C11 109.49(11) . . ?
O13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
O13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C14 O13 C12 112.44(10) . . ?
O13 C14 C15 115.90(11) . . ?
O13 C14 H14A 108.3 . . ?
C15 C14 H14A 108.3 . . ?
O13 C14 H14B 108.3 . . ?
C15 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
O16 C15 C14 116.09(11) . . ?
O16 C15 H15A 108.3 . . ?
C14 C15 H15A 108.3 . . ?
O16 C15 H15B 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C17 O16 C15 113.08(10) . . ?
O16 C17 C18 110.16(11) . . ?
O16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
O1 C18 C17 109.53(11) . . ?
O1 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C1G N1G H1N1 118.9(12) . . ?
C1G N1G H2N1 121.6(12) . . ?
H1N1 N1G H2N1 117.8(16) . . ?
C1G N2G N3G 121.71(11) . . ?
C1G N2G H1N2 121.1(11) . . ?
N3G N2G H1N2 115.2(11) . . ?
C2G N3G N2G 122.27(12) . . ?
C2G N3G H1N3 119.4(12) . . ?
N2G N3G H1N3 115.8(11) . . ?
C2G N4G H1N4 118.2(12) . . ?
C2G N4G H2N4 121.1(11) . . ?
H1N4 N4G H2N4 118.3(16) . . ?
N1G C1G N2G 117.00(12) . . ?
N1G C1G S1G 123.52(11) . . ?
N2G C1G S1G 119.48(10) . . ?
N4G C2G N3G 116.63(12) . . ?
N4G C2G S2G 124.43(11) . . ?
N3G C2G S2G 118.92(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 -58.51(14) . . . . ?
C2 C3 O4 C5 176.03(11) . . . . ?
C3 O4 C5 C6 -173.80(11) . . . . ?
O4 C5 C6 O7 70.29(14) . . . . ?
C5 C6 O7 C8 -169.25(11) . . . . ?
C6 O7 C8 C9 -179.21(11) . . . . ?
O7 C8 C9 O10 -60.10(14) . . . . ?
C8 C9 O10 C11 -173.23(10) . . . . ?
C9 O10 C11 C12 -161.96(11) . . . . ?
O10 C11 C12 O13 -58.15(14) . . . . ?
C11 C12 O13 C14 -170.60(11) . . . . ?
C12 O13 C14 C15 -60.83(15) . . . . ?
O13 C14 C15 O16 -54.22(17) . . . . ?
C14 C15 O16 C17 -53.39(16) . . . . ?
C15 O16 C17 C18 -171.54(11) . . . . ?
O16 C17 C18 O1 -61.45(14) . . . . ?
C17 C18 O1 C2 -163.14(10) . . . . ?
C18 O1 C2 C3 -171.81(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1G H2N1 O1 0.847(18) 2.233(19) 3.0563(16) 163.8(16) .
N1G H1N1 O7 0.876(19) 2.15(2) 3.0067(16) 164.6(16) .
N2G H1N2 O13 0.802(16) 2.276(16) 2.9819(16) 147.1(15) 1_545
N3G H1N3 O16 0.790(16) 2.216(17) 2.9326(16) 151.0(15) .
N4G H1N4 O4 0.824(18) 2.378(19) 3.1632(17) 159.5(16) 1_545
N4G H2N4 O10 0.876(18) 2.201(19) 3.0576(16) 166.1(15) 1_545

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049

data_compound_5
_database_code_CSD               202648

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
cis-anti-cis isomer (B) (2,3,11,12-dicyclohexano-
1,4,7,10,13,16-hexaoxacyclooctadecane
N,N'-(thiocarbamoyl)hydrazine clathrate
;
_chemical_name_common            
;
cis-anti-cis isomer (B) (2,3,11,12-dicyclohexano-
1,4,7,10,13,16-hexaoxacyclooctadecane N,N'-(thiocarbamoyl)hydrazine
clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H36 O6 , C2 H6 N4 S2'
_chemical_formula_sum            'C22 H42 N4 O6 S2'
_chemical_formula_weight         522.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   12.489(2)
_cell_length_b                   7.509(2)
_cell_length_c                   14.639(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.61(3)
_cell_angle_gamma                90.00
_cell_volume                     1370.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3097
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3097
_reflns_number_gt                3019
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3229P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_number_reflns         3097
_refine_ls_number_parameters     331
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2G S 0.85262(4) 0.12468(7) 0.94266(4) 0.03093(15) Uani 1 1 d . . .
S1G S 1.34152(4) 0.38230(7) 1.04010(4) 0.03146(15) Uani 1 1 d . . .
C1G C 1.20744(19) 0.3915(3) 1.01767(16) 0.0226(5) Uani 1 1 d . . .
C2G C 0.98610(19) 0.1179(3) 0.97120(15) 0.0215(4) Uani 1 1 d . . .
N1G N 1.14784(18) 0.5249(3) 1.04569(16) 0.0325(4) Uani 1 1 d . . .
H1N1 H 1.183(3) 0.619(6) 1.074(3) 0.068(12) Uiso 1 1 d . . .
H2N1 H 1.079(3) 0.527(5) 1.031(2) 0.052(10) Uiso 1 1 d . . .
N2G N 1.15789(15) 0.2609(2) 0.96850(14) 0.0248(4) Uani 1 1 d . . .
H1N2 H 1.194(2) 0.186(4) 0.9404(19) 0.026(7) Uiso 1 1 d . . .
N3G N 1.04722(15) 0.2580(3) 0.94868(15) 0.0262(4) Uani 1 1 d . . .
H1N3 H 1.023(3) 0.348(5) 0.922(2) 0.040(8) Uiso 1 1 d . . .
N4G N 1.03452(16) -0.0171(3) 1.01455(14) 0.0271(4) Uani 1 1 d . . .
H1N4 H 0.998(2) -0.111(4) 1.0312(18) 0.022(6) Uiso 1 1 d . . .
H2N4 H 1.106(3) -0.021(4) 1.0191(19) 0.029(7) Uiso 1 1 d . . .
O1 O 1.12381(12) 0.8053(2) 1.20164(10) 0.0239(3) Uani 1 1 d . . .
C2 C 1.18880(18) 0.9596(3) 1.21250(16) 0.0276(5) Uani 1 1 d . . .
H2A H 1.2073 0.9811 1.2769 0.033 Uiso 1 1 calc R . .
H2B H 1.1505 1.0627 1.1875 0.033 Uiso 1 1 calc R . .
C3 C 1.28876(19) 0.9285(3) 1.16245(15) 0.0273(5) Uani 1 1 d . . .
H3A H 1.3343 1.0332 1.1670 0.033 Uiso 1 1 calc R . .
H3B H 1.3286 0.8288 1.1895 0.033 Uiso 1 1 calc R . .
O4 O 1.25857(13) 0.8916(2) 1.06885(11) 0.0237(3) Uani 1 1 d . . .
C5 C 1.34943(19) 0.8812(3) 1.01485(16) 0.0233(5) Uani 1 1 d . . .
H5A H 1.3999 0.7939 1.0408 0.028 Uiso 1 1 calc R . .
H5B H 1.3853 0.9957 1.0143 0.028 Uiso 1 1 calc R . .
C6 C 1.31271(18) 0.8281(3) 0.91850(15) 0.0250(4) Uani 1 1 d . . .
H6A H 1.3745 0.8071 0.8830 0.030 Uiso 1 1 calc R . .
H6B H 1.2715 0.7187 0.9196 0.030 Uiso 1 1 calc R . .
O7 O 1.24823(12) 0.9663(2) 0.87705(10) 0.0232(3) Uani 1 1 d . . .
C8 C 1.23197(17) 0.9501(3) 0.77945(15) 0.0228(4) Uani 1 1 d . . .
H8 H 1.3023 0.9510 0.7534 0.027 Uiso 1 1 calc R . .
C9 C 1.17375(18) 0.7789(3) 0.74880(15) 0.0249(4) Uani 1 1 d . . .
H9 H 1.2160 0.6755 0.7704 0.030 Uiso 1 1 calc R . .
O10 O 1.07358(13) 0.7807(2) 0.79115(11) 0.0269(3) Uani 1 1 d . . .
C11 C 1.0096(2) 0.6277(3) 0.77261(15) 0.0305(5) Uani 1 1 d . . .
H11A H 1.0496 0.5215 0.7912 0.037 Uiso 1 1 calc R . .
H11B H 0.9906 0.6196 0.7075 0.037 Uiso 1 1 calc R . .
C12 C 0.9092(2) 0.6404(4) 0.82461(17) 0.0316(5) Uani 1 1 d . . .
H12A H 0.8802 0.7601 0.8193 0.038 Uiso 1 1 calc R . .
H12B H 0.8556 0.5584 0.7985 0.038 Uiso 1 1 calc R . .
O13 O 0.93293(13) 0.5984(2) 0.91894(11) 0.0235(3) Uani 1 1 d . . .
C14 C 0.83853(19) 0.6127(3) 0.96842(17) 0.0261(5) Uani 1 1 d . . .
H14A H 0.7823 0.5380 0.9402 0.031 Uiso 1 1 calc R . .
H14B H 0.8133 0.7349 0.9672 0.031 Uiso 1 1 calc R . .
C15 C 0.86400(17) 0.5547(3) 1.06607(15) 0.0249(4) Uani 1 1 d . . .
H15A H 0.7994 0.5562 1.0995 0.030 Uiso 1 1 calc R . .
H15B H 0.8923 0.4344 1.0673 0.030 Uiso 1 1 calc R . .
O16 O 0.94144(12) 0.6743(2) 1.10745(10) 0.0247(3) Uani 1 1 d . . .
C17 C 0.95466(17) 0.6628(3) 1.20519(15) 0.0235(4) Uani 1 1 d . . .
H17 H 0.8835 0.6730 1.2294 0.028 Uiso 1 1 calc R . .
C18 C 1.02029(17) 0.8226(3) 1.23842(15) 0.0241(4) Uani 1 1 d . . .
H18 H 0.9856 0.9322 1.2154 0.029 Uiso 1 1 calc R . .
C19 C 1.0288(2) 0.8252(3) 1.34327(15) 0.0300(5) Uani 1 1 d . . .
H19A H 1.0716 0.9264 1.3647 0.036 Uiso 1 1 calc R . .
H19B H 0.9578 0.8375 1.3659 0.036 Uiso 1 1 calc R . .
C20 C 1.0806(2) 0.6531(4) 1.38029(17) 0.0352(5) Uani 1 1 d . . .
H20A H 1.1536 0.6458 1.3616 0.042 Uiso 1 1 calc R . .
H20B H 1.0832 0.6545 1.4466 0.042 Uiso 1 1 calc R . .
C21 C 1.0178(2) 0.4914(3) 1.34496(17) 0.0349(5) Uani 1 1 d . . .
H21A H 0.9476 0.4919 1.3697 0.042 Uiso 1 1 calc R . .
H21B H 1.0548 0.3841 1.3662 0.042 Uiso 1 1 calc R . .
C22 C 1.00449(19) 0.4887(3) 1.24002(16) 0.0282(5) Uani 1 1 d . . .
H22A H 1.0739 0.4725 1.2150 0.034 Uiso 1 1 calc R . .
H22B H 0.9589 0.3897 1.2200 0.034 Uiso 1 1 calc R . .
C23 C 1.17067(19) 1.1138(3) 0.74539(16) 0.0269(4) Uani 1 1 d . . .
H23A H 1.2094 1.2202 0.7655 0.032 Uiso 1 1 calc R . .
H23B H 1.1008 1.1162 0.7709 0.032 Uiso 1 1 calc R . .
C24 C 1.1567(2) 1.1115(3) 0.64085(17) 0.0336(5) Uani 1 1 d . . .
H24A H 1.1142 1.2135 0.6199 0.040 Uiso 1 1 calc R . .
H24B H 1.2264 1.1206 0.6155 0.040 Uiso 1 1 calc R . .
C25 C 1.1015(2) 0.9410(4) 0.60673(16) 0.0320(5) Uani 1 1 d . . .
H25A H 1.0982 0.9386 0.5404 0.038 Uiso 1 1 calc R . .
H25B H 1.0286 0.9386 0.6261 0.038 Uiso 1 1 calc R . .
C26 C 1.16212(19) 0.7780(3) 0.64418(16) 0.0295(5) Uani 1 1 d . . .
H26A H 1.2328 0.7753 0.6203 0.035 Uiso 1 1 calc R . .
H26B H 1.1242 0.6712 0.6235 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2G 0.0217(3) 0.0236(3) 0.0465(4) -0.0017(2) -0.0062(2) -0.0008(2)
S1G 0.0243(3) 0.0249(3) 0.0443(4) 0.0000(2) -0.0047(2) -0.0011(2)
C1G 0.0259(12) 0.0196(10) 0.0227(10) 0.0010(7) 0.0051(9) -0.0022(8)
C2G 0.0237(11) 0.0187(10) 0.0219(10) -0.0026(7) 0.0016(9) 0.0005(7)
N1G 0.0269(10) 0.0262(10) 0.0452(12) -0.0132(9) 0.0078(9) -0.0010(8)
N2G 0.0208(8) 0.0200(8) 0.0342(10) -0.0050(7) 0.0054(7) 0.0005(7)
N3G 0.0209(9) 0.0185(9) 0.0389(10) 0.0039(8) 0.0001(7) 0.0012(7)
N4G 0.0211(9) 0.0241(9) 0.0355(10) 0.0076(8) -0.0031(7) -0.0018(7)
O1 0.0226(7) 0.0227(7) 0.0268(7) -0.0025(6) 0.0047(6) -0.0026(6)
C2 0.0305(11) 0.0260(11) 0.0262(11) -0.0047(9) 0.0021(8) -0.0071(9)
C3 0.0248(11) 0.0342(11) 0.0224(11) -0.0011(9) -0.0022(9) -0.0076(9)
O4 0.0207(8) 0.0280(8) 0.0221(8) -0.0016(6) 0.0005(6) -0.0017(6)
C5 0.0179(10) 0.0229(10) 0.0289(12) -0.0010(8) -0.0012(9) 0.0015(7)
C6 0.0266(10) 0.0209(10) 0.0275(11) -0.0012(8) 0.0021(8) 0.0047(8)
O7 0.0249(7) 0.0227(7) 0.0216(7) -0.0017(6) -0.0007(6) 0.0039(6)
C8 0.0211(9) 0.0261(11) 0.0216(10) -0.0009(8) 0.0039(8) 0.0002(8)
C9 0.0279(10) 0.0248(10) 0.0220(10) -0.0023(8) 0.0018(8) 0.0015(8)
O10 0.0282(8) 0.0255(7) 0.0272(8) -0.0027(6) 0.0046(6) -0.0038(6)
C11 0.0382(13) 0.0308(12) 0.0224(11) -0.0018(8) 0.0010(9) -0.0127(9)
C12 0.0304(12) 0.0382(13) 0.0251(11) 0.0068(9) -0.0064(9) -0.0083(10)
O13 0.0215(8) 0.0251(7) 0.0237(8) 0.0024(6) -0.0001(6) -0.0014(6)
C14 0.0177(11) 0.0270(12) 0.0332(13) -0.0066(8) -0.0008(9) -0.0004(8)
C15 0.0208(10) 0.0236(10) 0.0308(11) -0.0028(8) 0.0045(8) -0.0053(8)
O16 0.0238(7) 0.0261(7) 0.0241(7) 0.0002(6) 0.0017(6) -0.0071(6)
C17 0.0239(10) 0.0259(10) 0.0212(10) -0.0013(8) 0.0047(8) -0.0019(8)
C18 0.0237(10) 0.0232(10) 0.0257(10) -0.0016(8) 0.0048(8) 0.0014(8)
C19 0.0361(12) 0.0313(11) 0.0233(10) -0.0052(9) 0.0063(9) -0.0040(10)
C20 0.0403(14) 0.0381(13) 0.0268(12) 0.0047(10) 0.0002(10) -0.0034(11)
C21 0.0445(14) 0.0314(12) 0.0288(12) 0.0067(10) 0.0035(10) -0.0044(11)
C22 0.0303(11) 0.0238(10) 0.0307(11) 0.0027(9) 0.0033(9) -0.0017(9)
C23 0.0290(11) 0.0256(11) 0.0264(11) 0.0026(8) 0.0028(8) 0.0003(9)
C24 0.0360(13) 0.0372(14) 0.0275(12) 0.0067(10) 0.0029(10) 0.0021(10)
C25 0.0362(12) 0.0394(13) 0.0199(10) 0.0007(9) -0.0014(9) 0.0027(10)
C26 0.0319(11) 0.0316(12) 0.0250(11) -0.0039(9) 0.0027(9) 0.0017(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2G C2G 1.694(2) . ?
S1G C1G 1.687(2) . ?
C1G N1G 1.328(3) . ?
C1G N2G 1.345(3) . ?
C2G N4G 1.322(3) . ?
C2G N3G 1.353(3) . ?
N1G H1N1 0.92(5) . ?
N1G H2N1 0.87(4) . ?
N2G N3G 1.394(3) . ?
N2G H1N2 0.84(3) . ?
N3G H1N3 0.83(4) . ?
N4G H1N4 0.88(3) . ?
N4G H2N4 0.89(3) . ?
O1 C2 1.418(3) . ?
O1 C18 1.437(2) . ?
C2 C3 1.505(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.425(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.425(3) . ?
C5 C6 1.509(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.425(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.436(3) . ?
C8 C23 1.516(3) . ?
C8 C9 1.530(3) . ?
C8 H8 0.9800 . ?
C9 O10 1.431(3) . ?
C9 C26 1.529(3) . ?
C9 H9 0.9800 . ?
O10 C11 1.416(3) . ?
C11 C12 1.510(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O13 1.429(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O13 C14 1.426(3) . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O16 1.427(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O16 C17 1.433(3) . ?
C17 C18 1.516(3) . ?
C17 C22 1.522(3) . ?
C17 H17 0.9800 . ?
C18 C19 1.532(3) . ?
C18 H18 0.9800 . ?
C19 C20 1.529(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.519(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.535(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.529(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.523(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.524(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1G C1G N2G 117.9(2) . . ?
N1G C1G S1G 122.66(18) . . ?
N2G C1G S1G 119.46(17) . . ?
N4G C2G N3G 117.7(2) . . ?
N4G C2G S2G 123.69(17) . . ?
N3G C2G S2G 118.58(17) . . ?
C1G N1G H1N1 117(3) . . ?
C1G N1G H2N1 120(2) . . ?
H1N1 N1G H2N1 122(4) . . ?
C1G N2G N3G 122.64(19) . . ?
C1G N2G H1N2 120.8(19) . . ?
N3G N2G H1N2 115.8(19) . . ?
C2G N3G N2G 121.90(19) . . ?
C2G N3G H1N3 124(2) . . ?
N2G N3G H1N3 114(2) . . ?
C2G N4G H1N4 121.1(18) . . ?
C2G N4G H2N4 119.1(19) . . ?
H1N4 N4G H2N4 119(3) . . ?
C2 O1 C18 113.97(16) . . ?
O1 C2 C3 107.76(18) . . ?
O1 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O4 C3 C2 108.72(19) . . ?
O4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
O4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C3 O4 C5 111.85(18) . . ?
O4 C5 C6 109.10(19) . . ?
O4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
O4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
O7 C6 C5 109.64(17) . . ?
O7 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
O7 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C6 O7 C8 113.75(16) . . ?
O7 C8 C23 107.18(17) . . ?
O7 C8 C9 113.45(17) . . ?
C23 C8 C9 111.34(18) . . ?
O7 C8 H8 108.2 . . ?
C23 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
O10 C9 C26 113.79(18) . . ?
O10 C9 C8 106.11(16) . . ?
C26 C9 C8 108.12(18) . . ?
O10 C9 H9 109.6 . . ?
C26 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
C11 O10 C9 114.04(17) . . ?
O10 C11 C12 109.15(19) . . ?
O10 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
O10 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
O13 C12 C11 110.2(2) . . ?
O13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
O13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 O13 C12 110.27(19) . . ?
O13 C14 C15 109.13(19) . . ?
O13 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
O13 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O16 C15 C14 108.50(17) . . ?
O16 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
O16 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C15 O16 C17 114.74(16) . . ?
O16 C17 C18 107.39(17) . . ?
O16 C17 C22 113.90(18) . . ?
C18 C17 C22 111.78(19) . . ?
O16 C17 H17 107.8 . . ?
C18 C17 H17 107.8 . . ?
C22 C17 H17 107.8 . . ?
O1 C18 C17 106.82(17) . . ?
O1 C18 C19 111.67(19) . . ?
C17 C18 C19 109.48(18) . . ?
O1 C18 H18 109.6 . . ?
C17 C18 H18 109.6 . . ?
C19 C18 H18 109.6 . . ?
C20 C19 C18 110.22(19) . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 110.9(2) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 C22 111.9(2) . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C17 C22 C21 109.88(19) . . ?
C17 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C17 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C8 C23 C24 110.08(18) . . ?
C8 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C8 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.2 . . ?
C25 C24 C23 111.01(19) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 110.6(2) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 C9 111.75(19) . . ?
C25 C26 H26A 109.3 . . ?
C9 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
C9 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 57.9(2) . . . . ?
C2 C3 O4 C5 173.17(18) . . . . ?
C3 O4 C5 C6 175.68(18) . . . . ?
O4 C5 C6 O7 66.0(2) . . . . ?
C5 C6 O7 C8 165.06(17) . . . . ?
C6 O7 C8 C9 61.4(2) . . . . ?
O7 C8 C9 O10 57.8(2) . . . . ?
C8 C9 O10 C11 -178.05(18) . . . . ?
C9 O10 C11 C12 177.11(18) . . . . ?
O10 C11 C12 O13 -77.0(2) . . . . ?
C11 C12 O13 C14 179.22(18) . . . . ?
C12 O13 C14 C15 175.89(18) . . . . ?
O13 C14 C15 O16 63.4(2) . . . . ?
C14 C15 O16 C17 165.79(18) . . . . ?
C15 O16 C17 C18 -168.07(17) . . . . ?
O16 C17 C18 O1 -63.7(2) . . . . ?
C17 C18 O1 C2 169.29(17) . . . . ?
C18 O1 C2 C3 -174.17(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1G H1N1 O4 0.92(5) 2.26(4) 3.091(3) 150(4) .
N1G H2N1 O13 0.87(4) 2.43(4) 3.213(3) 149(3) .
N1G H2N1 O16 0.87(4) 2.38(4) 3.002(3) 128(3) .
N2G H1N2 O7 0.84(3) 2.03(3) 2.855(2) 166(3) 1_545
N3G H1N3 O13 0.83(4) 2.19(4) 2.946(3) 151(3) .
N4G H1N4 O16 0.88(3) 2.11(3) 2.961(3) 163(2) 1_545
N4G H2N4 O4 0.89(3) 2.11(3) 2.941(3) 157(3) 1_545

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039

data_compound_6
_database_code_CSD               202649

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4,7,10,13-pentaoxacyclopentadecane
bis[N,N'-(thiocarbamoyl)hydrazine] clathrate
;
_chemical_name_common            
;
1,4,7,10,13-pentaoxacyclopentadecane bis(N,N'-
(thiocarbamoyl)hydrazine) clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H20 O5 , 2(C2 H6 N4 S2)'
_chemical_formula_sum            'C14 H32 N8 O5 S4'
_chemical_formula_weight         520.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.632(3)
_cell_length_b                   9.475(2)
_cell_length_c                   19.185(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2478.0(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.424
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3579
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         29.91
_reflns_number_total             3579
_reflns_number_gt                3158
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+1.7325P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3579
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1G S 0.13368(3) 0.35717(4) 0.11670(2) 0.02684(10) Uani 1 1 d . . .
S2G S 0.13357(3) -0.25142(4) 0.26918(2) 0.03093(11) Uani 1 1 d . . .
N1G N 0.08359(13) 0.09126(15) 0.09058(8) 0.0377(4) Uani 1 1 d . . .
H1GA H 0.053(2) 0.124(3) 0.0572(15) 0.081(9) Uiso 1 1 d . . .
H1GB H 0.0806(15) 0.003(2) 0.0989(10) 0.040(5) Uiso 1 1 d . . .
N2G N 0.16623(10) 0.13090(12) 0.19220(7) 0.0276(3) Uani 1 1 d . . .
H2GA H 0.2097(15) 0.180(2) 0.2141(10) 0.040(5) Uiso 1 1 d . . .
N3G N 0.17429(9) -0.01414(12) 0.20350(7) 0.0249(2) Uani 1 1 d . . .
H3GA H 0.2249(16) -0.057(2) 0.1847(10) 0.044(6) Uiso 1 1 d . . .
N4G N 0.03687(10) -0.00914(13) 0.27242(7) 0.0276(3) Uani 1 1 d . . .
H4GA H -0.0034(16) -0.052(2) 0.3010(11) 0.044(6) Uiso 1 1 d . . .
H4GB H 0.0224(15) 0.078(2) 0.2581(11) 0.039(5) Uiso 1 1 d . . .
C2G C 0.11261(10) -0.08067(14) 0.24757(7) 0.0219(3) Uani 1 1 d . . .
C1G C 0.12699(9) 0.18043(14) 0.13232(7) 0.0205(3) Uani 1 1 d . . .
O1 O -0.1277(2) -0.1247(3) 0.06671(13) 0.0282(5) Uani 0.50 1 d P . .
C2 C -0.1697(3) -0.0078(5) 0.10107(18) 0.0364(8) Uani 0.50 1 d P . .
H2A H -0.1264 0.0262 0.1368 0.044 Uiso 0.50 1 d PR . .
H2B H -0.2307 -0.0343 0.1224 0.044 Uiso 0.50 1 d PR . .
C3 C -0.1882(7) 0.1103(10) 0.0473(5) 0.0356(16) Uani 0.50 1 d P . .
H3A H -0.2201 0.1893 0.0690 0.043 Uiso 0.50 1 d PR . .
H3B H -0.2307 0.0750 0.0114 0.043 Uiso 0.50 1 d PR . .
O4 O -0.10065(16) 0.1530(2) 0.01696(12) 0.0303(5) Uani 0.50 1 d P . .
C5 C -0.1098(4) 0.2702(5) -0.0277(3) 0.0435(11) Uani 0.50 1 d P . .
H5A H -0.1286 0.3537 -0.0027 0.052 Uiso 0.50 1 d PR . .
H5B H -0.1595 0.2503 -0.0618 0.052 Uiso 0.50 1 d PR . .
C6 C -0.0146(13) 0.2963(13) -0.0629(10) 0.036(3) Uani 0.50 1 d P . .
H6A H 0.0390 0.2961 -0.0305 0.043 Uiso 0.50 1 d PR . .
H6B H -0.0141 0.3826 -0.0892 0.043 Uiso 0.50 1 d PR . .
O7 O -0.00004(17) 0.1822(3) -0.11147(12) 0.0339(5) Uani 0.50 1 d P . .
C8 C 0.0981(3) 0.1665(5) -0.1354(2) 0.0405(10) Uani 0.50 1 d P . .
H8A H 0.1246 0.2590 -0.1430 0.049 Uiso 0.50 1 d PR . .
H8B H 0.0979 0.1177 -0.1792 0.049 Uiso 0.50 1 d PR . .
C9 C 0.1636(3) 0.0858(6) -0.0821(3) 0.0458(11) Uani 0.50 1 d P . .
H9A H 0.1685 0.1379 -0.0393 0.055 Uiso 0.50 1 d PR . .
H9B H 0.2283 0.0758 -0.1012 0.055 Uiso 0.50 1 d PR . .
O10 O 0.1227(2) -0.0439(3) -0.07038(15) 0.0437(6) Uani 0.50 1 d P . .
C11 C 0.1895(9) -0.1259(14) -0.0300(6) 0.059(3) Uani 0.50 1 d P . .
H11A H 0.2134 -0.0717 0.0087 0.071 Uiso 0.50 1 d PR . .
H11B H 0.2441 -0.1574 -0.0575 0.071 Uiso 0.50 1 d PR . .
C12 C 0.1269(4) -0.2543(6) -0.0047(3) 0.0490(13) Uani 0.50 1 d P . .
H12A H 0.1670 -0.3263 0.0160 0.059 Uiso 0.50 1 d PR . .
H12B H 0.0912 -0.2946 -0.0430 0.059 Uiso 0.50 1 d PR . .
O13 O 0.06177(19) -0.1984(3) 0.04588(13) 0.0381(5) Uani 0.50 1 d P . .
C14 C -0.0062(14) -0.2983(16) 0.0710(11) 0.039(3) Uani 0.50 1 d P . .
H14A H 0.0305 -0.3644 0.0985 0.047 Uiso 0.50 1 d PR . .
H14B H -0.0327 -0.3462 0.0311 0.047 Uiso 0.50 1 d PR . .
C15 C -0.0811(3) -0.2202(4) 0.1125(2) 0.0343(8) Uani 0.50 1 d P . .
H15A H -0.1267 -0.2901 0.1287 0.041 Uiso 0.50 1 d PR . .
H15B H -0.0541 -0.1718 0.1520 0.041 Uiso 0.50 1 d PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1G 0.0329(2) 0.01553(16) 0.03209(19) 0.00510(13) -0.00232(14) 0.00256(13)
S2G 0.02526(18) 0.01670(16) 0.0508(2) 0.01212(15) 0.00529(15) 0.00062(13)
N1G 0.0604(10) 0.0201(6) 0.0326(7) 0.0028(5) -0.0174(7) -0.0024(6)
N2G 0.0359(7) 0.0149(5) 0.0322(6) 0.0069(5) -0.0100(5) -0.0073(5)
N3G 0.0248(6) 0.0153(5) 0.0346(6) 0.0078(5) -0.0003(5) -0.0014(4)
N4G 0.0322(7) 0.0177(6) 0.0329(6) 0.0027(5) 0.0031(5) 0.0012(5)
C2G 0.0229(6) 0.0164(5) 0.0264(6) 0.0026(5) -0.0047(5) -0.0030(5)
C1G 0.0192(6) 0.0169(5) 0.0252(6) 0.0017(5) 0.0032(5) 0.0025(5)
O1 0.0356(16) 0.0221(12) 0.0268(11) 0.0017(9) -0.0067(11) -0.0006(10)
C2 0.0372(18) 0.041(2) 0.0311(16) -0.0094(15) 0.0173(14) -0.0138(16)
C3 0.022(2) 0.042(3) 0.043(4) -0.009(3) -0.004(2) 0.008(2)
O4 0.0279(11) 0.0247(11) 0.0382(12) 0.0026(9) -0.0023(9) -0.0008(9)
C5 0.049(3) 0.0261(18) 0.056(3) 0.003(2) -0.006(2) 0.0124(18)
C6 0.052(7) 0.012(2) 0.043(6) 0.003(2) -0.013(4) 0.000(3)
O7 0.0343(12) 0.0312(11) 0.0363(12) 0.0022(10) -0.0098(9) -0.0053(9)
C8 0.042(2) 0.042(2) 0.038(2) 0.0028(17) -0.0035(18) -0.0171(19)
C9 0.029(2) 0.041(3) 0.068(3) -0.005(2) -0.010(2) -0.0040(19)
O10 0.0445(15) 0.0365(13) 0.0500(15) 0.0043(12) -0.0080(12) 0.0027(11)
C11 0.044(3) 0.083(5) 0.051(5) 0.010(3) 0.001(3) 0.039(3)
C12 0.042(2) 0.046(3) 0.059(3) -0.011(3) 0.003(2) 0.023(2)
O13 0.0403(13) 0.0324(12) 0.0414(13) -0.0058(11) 0.0037(11) 0.0022(11)
C14 0.051(7) 0.031(3) 0.035(3) 0.008(2) -0.007(4) 0.000(3)
C15 0.038(2) 0.032(2) 0.033(2) 0.0140(15) -0.0127(16) -0.0118(16)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1G C1G 1.7037(14) . ?
S2G C2G 1.6943(14) . ?
N1G C1G 1.306(2) . ?
N1G H1GA 0.82(3) . ?
N1G H1GB 0.85(2) . ?
N2G C1G 1.3512(18) . ?
N2G N3G 1.3956(16) . ?
N2G H2GA 0.86(2) . ?
N3G C2G 1.3489(18) . ?
N3G H3GA 0.88(2) . ?
N4G C2G 1.3240(19) . ?
N4G H4GA 0.88(2) . ?
N4G H4GB 0.89(2) . ?
O1 C9 0.679(5) 5 ?
O1 C2 1.411(4) . ?
O1 C15 1.413(4) . ?
O1 C8 1.434(5) 5 ?
O1 O10 1.601(4) 5 ?
C2 C9 0.829(6) 5 ?
C2 O10 0.999(4) 5 ?
C2 C3 1.543(11) . ?
C2 C11 1.880(12) 5 ?
C2 C8 1.910(7) 5 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C3 C11 0.36(2) 5 ?
C3 O10 1.180(11) 5 ?
C3 O4 1.388(10) . ?
C3 C12 1.797(11) 5 ?
C3 C9 2.003(11) 5 ?
C3 H3A 0.9601 . ?
C3 H3B 0.9599 . ?
O4 C12 1.051(6) 5 ?
O4 C11 1.263(13) 5 ?
O4 O13 1.386(3) 5 ?
O4 C5 1.409(5) . ?
O4 O10 1.486(3) 5 ?
C5 C12 0.681(6) 5 ?
C5 O13 1.006(5) 5 ?
C5 C6 1.483(18) . ?
C5 C14 1.806(18) 5 ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C6 C14 0.32(3) 5 ?
C6 O13 1.175(15) 5 ?
C6 O7 1.440(16) . ?
C6 C15 1.768(17) 5 ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
O7 C15 1.163(5) 5 ?
O7 C14 1.349(19) 5 ?
O7 C8 1.422(5) . ?
O7 O13 1.521(3) 5 ?
C8 C15 0.711(5) 5 ?
C8 O1 1.434(5) 5 ?
C8 C9 1.558(7) . ?
C8 C2 1.910(7) 5 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9599 . ?
C9 O1 0.679(5) 5 ?
C9 C2 0.829(6) 5 ?
C9 O10 1.369(5) . ?
C9 C15 1.796(6) 5 ?
C9 C3 2.003(11) 5 ?
C9 H9A 0.9599 . ?
C9 H9B 0.9599 . ?
O10 C2 0.999(4) 5 ?
O10 C3 1.180(11) 5 ?
O10 C11 1.426(12) . ?
O10 O4 1.486(3) 5 ?
O10 O1 1.601(4) 5 ?
C11 C3 0.36(2) 5 ?
C11 O4 1.263(13) 5 ?
C11 C12 1.564(14) . ?
C11 C2 1.880(12) 5 ?
C11 H11A 0.9600 . ?
C11 H11B 0.9599 . ?
C12 C5 0.681(6) 5 ?
C12 O4 1.051(6) 5 ?
C12 O13 1.417(5) . ?
C12 C3 1.797(11) 5 ?
C12 H12A 0.9600 . ?
C12 H12B 0.9599 . ?
O13 C5 1.006(5) 5 ?
O13 C6 1.175(15) 5 ?
O13 O4 1.386(3) 5 ?
O13 C14 1.409(17) . ?
O13 O7 1.521(3) 5 ?
C14 C6 0.32(3) 5 ?
C14 O7 1.349(19) 5 ?
C14 C15 1.491(18) . ?
C14 C5 1.806(18) 5 ?
C14 H14A 0.9599 . ?
C14 H14B 0.9600 . ?
C15 C8 0.711(5) 5 ?
C15 O7 1.163(5) 5 ?
C15 C6 1.768(17) 5 ?
C15 C9 1.796(6) 5 ?
C15 H15A 0.9600 . ?
C15 H15B 0.9599 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1G N1G H1GA 117(2) . . ?
C1G N1G H1GB 122.8(14) . . ?
H1GA N1G H1GB 119(2) . . ?
C1G N2G N3G 120.34(12) . . ?
C1G N2G H2GA 119.8(14) . . ?
N3G N2G H2GA 113.8(14) . . ?
C2G N3G N2G 120.57(13) . . ?
C2G N3G H3GA 122.1(14) . . ?
N2G N3G H3GA 116.9(14) . . ?
C2G N4G H4GA 118.5(14) . . ?
C2G N4G H4GB 122.3(14) . . ?
H4GA N4G H4GB 118.9(19) . . ?
N4G C2G N3G 118.20(13) . . ?
N4G C2G S2G 122.16(11) . . ?
N3G C2G S2G 119.64(11) . . ?
N1G C1G N2G 118.43(13) . . ?
N1G C1G S1G 123.53(11) . . ?
N2G C1G S1G 118.01(10) . . ?
C9 O1 C2 23.0(5) 5 . ?
C9 O1 C15 113.6(6) 5 . ?
C2 O1 C15 113.3(3) . . ?
C9 O1 C8 87.3(6) 5 5 ?
C2 O1 C8 84.4(3) . 5 ?
C15 O1 C8 28.9(2) . 5 ?
C9 O1 O10 58.1(5) 5 5 ?
C2 O1 O10 38.09(17) . 5 ?
C15 O1 O10 126.3(3) . 5 ?
C8 O1 O10 102.9(3) 5 5 ?
C9 C2 O10 96.6(5) 5 5 ?
C9 C2 O1 18.7(4) 5 . ?
O10 C2 O1 81.3(3) 5 . ?
C9 C2 C3 111.7(6) 5 . ?
O10 C2 C3 49.9(4) 5 . ?
O1 C2 C3 108.9(4) . . ?
C9 C2 C11 107.3(6) 5 5 ?
O10 C2 C11 48.3(5) 5 5 ?
O1 C2 C11 104.4(5) . 5 ?
C3 C2 C11 4.5(7) . 5 ?
C9 C2 C8 52.9(5) 5 5 ?
O10 C2 C8 105.1(3) 5 5 ?
O1 C2 C8 48.3(2) . 5 ?
C3 C2 C8 152.3(5) . 5 ?
C11 C2 C8 148.6(5) 5 5 ?
C9 C2 H2A 123.4 5 . ?
O10 C2 H2A 82.0 5 . ?
O1 C2 H2A 110.3 . . ?
C3 C2 H2A 109.6 . . ?
C11 C2 H2A 112.3 5 . ?
C8 C2 H2A 72.7 5 . ?
C9 C2 H2B 92.4 5 . ?
O10 C2 H2B 159.3 5 . ?
O1 C2 H2B 110.2 . . ?
C3 C2 H2B 109.5 . . ?
C11 C2 H2B 111.2 5 . ?
C8 C2 H2B 95.2 5 . ?
H2A C2 H2B 108.4 . . ?
C11 C3 O10 127(4) 5 5 ?
C11 C3 O4 63(3) 5 . ?
O10 C3 O4 70.2(5) 5 . ?
C11 C3 C2 156(4) 5 . ?
O10 C3 C2 40.4(4) 5 . ?
O4 C3 C2 110.5(7) . . ?
C11 C3 C12 46(3) 5 5 ?
O10 C3 C12 102.9(6) 5 5 ?
O4 C3 C12 35.7(3) . 5 ?
C2 C3 C12 141.1(6) . 5 ?
C11 C3 C9 134(4) 5 5 ?
O10 C3 C9 41.7(4) 5 5 ?
O4 C3 C9 105.4(6) . 5 ?
C2 C3 C9 22.6(2) . 5 ?
C12 C3 C9 141.1(6) 5 5 ?
C11 C3 H3A 93.3 5 . ?
O10 C3 H3A 126.5 5 . ?
O4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.5 . . ?
C12 C3 H3A 79.4 5 . ?
C9 C3 H3A 130.9 5 . ?
C11 C3 H3B 57.2 5 . ?
O10 C3 H3B 122.8 5 . ?
O4 C3 H3B 108.7 . . ?
C2 C3 H3B 109.0 . . ?
C12 C3 H3B 102.7 5 . ?
C9 C3 H3B 91.0 5 . ?
H3A C3 H3B 108.1 . . ?
C12 O4 C11 84.5(7) 5 5 ?
C12 O4 O13 69.6(3) 5 5 ?
C11 O4 O13 127.0(5) 5 5 ?
C12 O4 C3 93.9(5) 5 . ?
C11 O4 C3 14.8(8) 5 . ?
O13 O4 C3 141.6(4) 5 . ?
C12 O4 C5 27.5(3) 5 . ?
C11 O4 C5 101.3(6) 5 . ?
O13 O4 C5 42.2(2) 5 . ?
C3 O4 C5 114.1(5) . . ?
C12 O4 O10 136.2(4) 5 5 ?
C11 O4 O10 61.9(5) 5 5 ?
O13 O4 O10 153.3(2) 5 5 ?
C3 O4 O10 48.3(4) . 5 ?
C5 O4 O10 161.9(3) . 5 ?
C12 C5 O13 112.9(9) 5 5 ?
C12 C5 O4 45.6(6) 5 . ?
O13 C5 O4 67.7(3) 5 . ?
C12 C5 C6 138.7(12) 5 . ?
O13 C5 C6 52.1(6) 5 . ?
O4 C5 C6 109.4(7) . . ?
C12 C5 C14 138.7(12) 5 5 ?
O13 C5 C14 51.0(6) 5 5 ?
O4 C5 C14 108.6(6) . 5 ?
C6 C5 C14 1.1(10) . 5 ?
C12 C5 H5A 68.5 5 . ?
O13 C5 H5A 154.7 5 . ?
O4 C5 H5A 111.7 . . ?
C6 C5 H5A 108.9 . . ?
C14 C5 H5A 110.0 5 . ?
C12 C5 H5B 109.7 5 . ?
O13 C5 H5B 95.2 5 . ?
O4 C5 H5B 108.8 . . ?
C6 C5 H5B 109.9 . . ?
C14 C5 H5B 109.5 5 . ?
H5A C5 H5B 108.2 . . ?
C14 C6 O13 131(5) 5 5 ?
C14 C6 O7 67(6) 5 . ?
O13 C6 O7 70.3(7) 5 . ?
C14 C6 C5 174(6) 5 . ?
O13 C6 C5 42.5(6) 5 . ?
O7 C6 C5 106.8(10) . . ?
C14 C6 C15 28(5) 5 5 ?
O13 C6 C15 103.4(9) 5 5 ?
O7 C6 C15 40.9(5) . 5 ?
C5 C6 C15 145.3(9) . 5 ?
C14 C6 H6A 68.9 5 . ?
O13 C6 H6A 103.6 5 . ?
O7 C6 H6A 108.2 . . ?
C5 C6 H6A 111.8 . . ?
C15 C6 H6A 77.6 5 . ?
C14 C6 H6B 72.2 5 . ?
O13 C6 H6B 145.3 5 . ?
O7 C6 H6B 107.4 . . ?
C5 C6 H6B 112.8 . . ?
C15 C6 H6B 93.4 5 . ?
H6A C6 H6B 109.6 . . ?
C15 O7 C14 72.4(8) 5 5 ?
C15 O7 C8 29.9(2) 5 . ?
C14 O7 C8 102.3(8) 5 . ?
C15 O7 C6 84.8(7) 5 . ?
C14 O7 C6 12.8(14) 5 . ?
C8 O7 C6 114.7(7) . . ?
C15 O7 O13 120.6(3) 5 5 ?
C14 O7 O13 58.4(7) 5 5 ?
C8 O7 O13 142.9(3) . 5 ?
C6 O7 O13 46.6(6) . 5 ?
C15 C8 O7 54.5(5) 5 . ?
C15 C8 O1 73.9(5) 5 5 ?
O7 C8 O1 89.9(3) . 5 ?
C15 C8 C9 97.6(6) 5 . ?
O7 C8 C9 112.3(4) . . ?
O1 C8 C9 25.8(2) 5 . ?
C15 C8 C2 121.2(6) 5 5 ?
O7 C8 C2 116.9(3) . 5 ?
O1 C8 C2 47.3(2) 5 5 ?
C9 C8 C2 25.1(2) . 5 ?
C15 C8 H8A 64.0 5 . ?
O7 C8 H8A 107.9 . . ?
O1 C8 H8A 106.6 5 . ?
C9 C8 H8A 109.4 . . ?
C2 C8 H8A 125.4 5 . ?
C15 C8 H8B 152.3 5 . ?
O7 C8 H8B 109.3 . . ?
O1 C8 H8B 132.3 5 . ?
C9 C8 H8B 109.9 . . ?
C2 C8 H8B 85.7 5 . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C2 138.4(8) 5 5 ?
O1 C9 O10 97.0(6) 5 . ?
C2 C9 O10 46.5(4) 5 . ?
O1 C9 C8 66.9(5) 5 . ?
C2 C9 C8 102.0(6) 5 . ?
O10 C9 C8 108.3(3) . . ?
O1 C9 C15 46.1(5) 5 5 ?
C2 C9 C15 123.6(6) 5 5 ?
O10 C9 C15 115.8(3) . 5 ?
C8 C9 C15 23.11(18) . 5 ?
O1 C9 C3 118.6(7) 5 5 ?
C2 C9 C3 45.7(5) 5 5 ?
O10 C9 C3 34.9(3) . 5 ?
C8 C9 C3 140.4(4) . 5 ?
C15 C9 C3 150.6(4) 5 5 ?
O1 C9 H9A 53.1 5 . ?
C2 C9 H9A 145.8 5 . ?
O10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.4 . . ?
C15 C9 H9A 87.5 5 . ?
C3 C9 H9A 100.4 5 . ?
O1 C9 H9B 151.7 5 . ?
C2 C9 H9B 69.6 5 . ?
O10 C9 H9B 110.4 . . ?
C8 C9 H9B 109.0 . . ?
C15 C9 H9B 121.4 5 . ?
C3 C9 H9B 83.2 5 . ?
H9A C9 H9B 108.2 . . ?
C2 O10 C3 89.8(6) 5 5 ?
C2 O10 C9 37.0(3) 5 . ?
C3 O10 C9 103.4(5) 5 . ?
C2 O10 C11 100.2(6) 5 . ?
C3 O10 C11 11.8(10) 5 . ?
C9 O10 C11 108.5(6) . . ?
C2 O10 O4 151.3(4) 5 5 ?
C3 O10 O4 61.5(5) 5 5 ?
C9 O10 O4 145.1(3) . 5 ?
C11 O10 O4 51.4(5) . 5 ?
C2 O10 O1 60.6(3) 5 5 ?
C3 O10 O1 118.9(4) 5 5 ?
C9 O10 O1 24.9(2) . 5 ?
C11 O10 O1 119.5(5) . 5 ?
O4 O10 O1 132.3(2) 5 5 ?
C3 C11 O4 103(4) 5 5 ?
C3 C11 O10 42(3) 5 . ?
O4 C11 O10 66.8(6) 5 . ?
C3 C11 C12 125(3) 5 . ?
O4 C11 C12 42.0(4) 5 . ?
O10 C11 C12 104.1(8) . . ?
C3 C11 C2 20(3) 5 5 ?
O4 C11 C2 98.2(7) 5 5 ?
O10 C11 C2 31.5(3) . 5 ?
C12 C11 C2 132.1(8) . 5 ?
C3 C11 H11A 120.4 5 . ?
O4 C11 H11A 106.3 5 . ?
O10 C11 H11A 110.2 . . ?
C12 C11 H11A 111.1 . . ?
C2 C11 H11A 104.5 5 . ?
C3 C11 H11B 70.3 5 . ?
O4 C11 H11B 142.1 5 . ?
O10 C11 H11B 111.5 . . ?
C12 C11 H11B 110.6 . . ?
C2 C11 H11B 85.6 5 . ?
H11A C11 H11B 109.2 . . ?
C5 C12 O4 106.9(8) 5 5 ?
C5 C12 O13 40.8(6) 5 . ?
O4 C12 O13 66.4(3) 5 . ?
C5 C12 C11 130.0(10) 5 . ?
O4 C12 C11 53.5(6) 5 . ?
O13 C12 C11 105.3(6) . . ?
C5 C12 C3 137.9(10) 5 5 ?
O4 C12 C3 50.4(4) 5 5 ?
O13 C12 C3 108.6(5) . 5 ?
C11 C12 C3 9.5(6) . 5 ?
C5 C12 H12A 70.2 5 . ?
O4 C12 H12A 159.2 5 . ?
O13 C12 H12A 109.9 . . ?
C11 C12 H12A 111.7 . . ?
C3 C12 H12A 117.5 5 . ?
C5 C12 H12B 116.0 5 . ?
O4 C12 H12B 91.1 5 . ?
O13 C12 H12B 110.8 . . ?
C11 C12 H12B 110.3 . . ?
C3 C12 H12B 100.9 5 . ?
H12A C12 H12B 108.8 . . ?
C5 O13 C6 85.3(8) 5 5 ?
C5 O13 O4 70.1(3) 5 5 ?
C6 O13 O4 134.2(10) 5 5 ?
C5 O13 C14 95.3(8) 5 . ?
C6 O13 C14 10.0(14) 5 . ?
O4 O13 C14 139.2(9) 5 . ?
C5 O13 C12 26.3(3) 5 . ?
C6 O13 C12 103.8(9) 5 . ?
O4 O13 C12 44.0(3) 5 . ?
C14 O13 C12 113.2(8) . . ?
C5 O13 O7 135.6(4) 5 5 ?
C6 O13 O7 63.0(8) 5 5 ?
O4 O13 O7 154.1(2) 5 5 ?
C14 O13 O7 54.7(8) . 5 ?
C12 O13 O7 161.8(3) . 5 ?
C6 C14 O7 100(6) 5 5 ?
C6 C14 O13 39(4) 5 . ?
O7 C14 O13 66.9(8) 5 . ?
C6 C14 C15 146(6) 5 . ?
O7 C14 C15 48.0(6) 5 . ?
O13 C14 C15 107.4(10) . . ?
C6 C14 C5 5(5) 5 5 ?
O7 C14 C5 95.1(10) 5 5 ?
O13 C14 C5 33.7(4) . 5 ?
C15 C14 C5 140.5(11) . 5 ?
C6 C14 H14A 80.9 5 . ?
O7 C14 H14A 100.5 5 . ?
O13 C14 H14A 106.4 . . ?
C15 C14 H14A 112.8 . . ?
C5 C14 H14A 83.8 5 . ?
C6 C14 H14B 88.8 5 . ?
O7 C14 H14B 150.2 5 . ?
O13 C14 H14B 107.0 . . ?
C15 C14 H14B 113.7 . . ?
C5 C14 H14B 91.9 5 . ?
H14A C14 H14B 109.0 . . ?
C8 C15 O7 95.6(6) 5 5 ?
C8 C15 O1 77.2(6) 5 . ?
O7 C15 O1 102.7(3) 5 . ?
C8 C15 C14 155.2(10) 5 . ?
O7 C15 C14 59.6(8) 5 . ?
O1 C15 C14 107.1(8) . . ?
C8 C15 C6 149.8(8) 5 5 ?
O7 C15 C6 54.2(6) 5 5 ?
O1 C15 C6 105.0(7) . 5 ?
C14 C15 C6 5.9(11) . 5 ?
C8 C15 C9 59.3(6) 5 5 ?
O7 C15 C9 111.7(3) 5 5 ?
O1 C15 C9 20.3(2) . 5 ?
C14 C15 C9 127.4(8) . 5 ?
C6 C15 C9 125.2(7) 5 5 ?
C8 C15 H15A 94.8 5 . ?
O7 C15 H15A 146.5 5 . ?
O1 C15 H15A 110.6 . . ?
C14 C15 H15A 105.9 . . ?
C6 C15 H15A 111.8 5 . ?
C9 C15 H15A 100.9 5 . ?
C8 C15 H15B 45.1 5 . ?
O7 C15 H15B 60.1 5 . ?
O1 C15 H15B 111.0 . . ?
C14 C15 H15B 113.4 . . ?
C6 C15 H15B 109.7 5 . ?
C9 C15 H15B 99.1 5 . ?
H15A C15 H15B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 -61.0(6) . . . . ?
C2 C3 O4 C5 -174.0(4) . . . . ?
C3 O4 C5 C6 -173.8(9) . . . . ?
O4 C5 C6 O7 70.2(12) . . . . ?
C5 C6 O7 C8 -162.9(7) . . . . ?
C6 O7 C8 C9 80.7(9) . . . . ?
O7 C8 C9 O10 58.3(6) . . . . ?
C8 C9 O10 C11 171.4(6) . . . . ?
C9 O10 C11 C12 166.7(6) . . . . ?
O10 C11 C12 O13 -71.6(8) . . . . ?
C11 C12 O13 C14 175.5(11) . . . . ?
C12 O13 C14 C15 -169.3(9) . . . . ?
O13 C14 C15 O1 61.6(14) . . . . ?
C14 C15 O1 C2 -155.8(8) . . . . ?
C15 O1 C2 C3 162.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3G H3GA S1G 0.88(2) 2.47(2) 3.3335(15) 169.9(18) 8_655
N2G H2GA S2G 0.86(2) 2.47(2) 3.2974(15) 160.6(18) 8_665
N4G H4GA S1G 0.88(2) 2.53(2) 3.3962(15) 171.7(19) 3_545
N4G H4GB S2G 0.89(2) 2.72(2) 3.4639(14) 141.5(17) 3
N1G H1GA O4 0.82(3) 2.25(3) 2.940(3) 141(3) .
N1G H1GA O1 0.82(3) 2.58(3) 3.093(3) 121(2) 5
N1G H1GB O7 0.85(2) 2.08(2) 2.859(3) 150.7(19) 5
N1G H1GB O13 0.85(2) 2.18(2) 2.891(3) 141.1(18) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.91
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.763
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.052

data_compound_7
_database_code_CSD               202650

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4,7,10-tetraoxacyclododecane
N,N'-(thiocarbamoyl)hydrazine clathrate
;
_chemical_name_common            
;1,4,7,10-tetraoxacyclododecane N,N'-(thiocarbamoyl)hydrazine
clathrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H16 O4 , C2 H6 N4 S2'
_chemical_formula_sum            'C10 H22 N4 O4 S2'
_chemical_formula_weight         326.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.475(4)
_cell_length_b                   18.445(4)
_cell_length_c                   9.443(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00
_cell_volume                     3217.9(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       phi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18662
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.10
_diffrn_reflns_theta_max         29.99
_reflns_number_total             9354
_reflns_number_gt                8171
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 2001)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III (Farrugia, 1997)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.1156P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9354
_refine_ls_number_parameters     404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S11G S 0.41386(2) 0.69079(2) 0.72929(5) 0.02254(9) Uani 1 1 d . . .
S12G S 0.60086(2) 0.66803(2) 1.31237(4) 0.02019(9) Uani 1 1 d . . .
N11G N 0.40432(8) 0.62495(8) 0.97825(16) 0.0242(3) Uani 1 1 d . . .
H1N H 0.3624(11) 0.6079(11) 0.950(2) 0.041(6) Uiso 1 1 d . . .
H2N H 0.4205(10) 0.6137(10) 1.064(2) 0.031(5) Uiso 1 1 d . . .
C11G C 0.44183(8) 0.66808(8) 0.89441(16) 0.0174(3) Uani 1 1 d . . .
N12G N 0.50646(7) 0.69356(7) 0.94202(14) 0.0181(3) Uani 1 1 d . . .
H3N H 0.5288(9) 0.7297(10) 0.896(2) 0.025(5) Uiso 1 1 d . . .
C12G C 0.58094(8) 0.65864(8) 1.13786(16) 0.0166(3) Uani 1 1 d . . .
N13G N 0.52097(7) 0.69103(7) 1.08718(14) 0.0185(3) Uani 1 1 d . . .
H4N H 0.4946(10) 0.7211(10) 1.136(2) 0.029(5) Uiso 1 1 d . . .
N14G N 0.62151(8) 0.62019(8) 1.04994(15) 0.0243(3) Uani 1 1 d . . .
H5N H 0.6627(10) 0.6018(10) 1.082(2) 0.031(5) Uiso 1 1 d . . .
H6N H 0.6108(11) 0.6132(10) 0.957(2) 0.034(5) Uiso 1 1 d . . .
S1G S -0.07109(2) 0.68238(2) 0.81922(4) 0.02220(9) Uani 1 1 d . . .
S2G S 0.11498(2) 0.67738(2) 0.23102(4) 0.02232(9) Uani 1 1 d . . .
N1G N -0.08823(8) 0.62613(8) 0.56310(15) 0.0246(3) Uani 1 1 d . . .
H7N H -0.1315(11) 0.6101(11) 0.591(2) 0.037(6) Uiso 1 1 d . . .
H8N H -0.0763(10) 0.6215(10) 0.469(2) 0.035(6) Uiso 1 1 d . . .
C1G C -0.04757(8) 0.66516(8) 0.64885(17) 0.0174(3) Uani 1 1 d . . .
N2G N 0.01669(7) 0.69118(7) 0.59919(14) 0.0180(3) Uani 1 1 d . . .
H9N H 0.0408(9) 0.7268(10) 0.647(2) 0.032(5) Uiso 1 1 d . . .
C2G C 0.09134(8) 0.66061(8) 0.40101(16) 0.0165(3) Uani 1 1 d . . .
N3G N 0.03013(7) 0.69092(7) 0.45380(14) 0.0184(3) Uani 1 1 d . . .
H10N H 0.0052(10) 0.7251(11) 0.406(2) 0.038(6) Uiso 1 1 d . . .
N4G N 0.12957(8) 0.61770(8) 0.48478(16) 0.0224(3) Uani 1 1 d . . .
H11N H 0.1182(11) 0.6119(10) 0.567(2) 0.031(5) Uiso 1 1 d . . .
H12N H 0.1661(10) 0.6010(10) 0.454(2) 0.022(5) Uiso 1 1 d . . .
O1A O 0.42177(5) 0.56460(6) 1.25565(12) 0.0213(2) Uani 1 1 d . . .
C2A C 0.47038(8) 0.50577(9) 1.28301(18) 0.0239(3) Uani 1 1 d . . .
H2A1 H 0.5084 0.5223 1.3460 0.029 Uiso 1 1 calc R . .
H2A2 H 0.4928 0.4910 1.1948 0.029 Uiso 1 1 calc R . .
C3A C 0.43323(9) 0.44136(9) 1.34857(18) 0.0251(3) Uani 1 1 d . . .
H3A1 H 0.4681 0.4031 1.3657 0.030 Uiso 1 1 calc R . .
H3A2 H 0.4118 0.4550 1.4385 0.030 Uiso 1 1 calc R . .
O4A O 0.37845(6) 0.41630(6) 1.25474(12) 0.0204(2) Uani 1 1 d . . .
C5A C 0.33400(9) 0.36051(9) 1.3136(2) 0.0263(4) Uani 1 1 d . . .
H5A1 H 0.3324 0.3654 1.4159 0.032 Uiso 1 1 calc R . .
H5A2 H 0.3543 0.3134 1.2911 0.032 Uiso 1 1 calc R . .
C6A C 0.25874(9) 0.36618(9) 1.2541(2) 0.0275(4) Uani 1 1 d . . .
H6A1 H 0.2615 0.3737 1.1526 0.033 Uiso 1 1 calc R . .
H6A2 H 0.2331 0.3211 1.2708 0.033 Uiso 1 1 calc R . .
O7A O 0.21935(6) 0.42464(6) 1.31714(13) 0.0236(2) Uani 1 1 d . . .
C8A C 0.20147(8) 0.48436(9) 1.22612(19) 0.0255(3) Uani 1 1 d . . .
H8A1 H 0.1572 0.5067 1.2598 0.031 Uiso 1 1 calc R . .
H8A2 H 0.1924 0.4660 1.1315 0.031 Uiso 1 1 calc R . .
C9A C 0.25950(8) 0.54087(9) 1.21888(17) 0.0212(3) Uani 1 1 d . . .
H9A1 H 0.3042 0.5193 1.1851 0.025 Uiso 1 1 calc R . .
H9A2 H 0.2454 0.5788 1.1533 0.025 Uiso 1 1 calc R . .
O10A O 0.27033(6) 0.57108(6) 1.35757(12) 0.0213(2) Uani 1 1 d . . .
C11A C 0.32201(9) 0.62910(8) 1.35908(19) 0.0249(3) Uani 1 1 d . . .
H11C H 0.3098 0.6624 1.4350 0.030 Uiso 1 1 calc R . .
H11D H 0.3187 0.6555 1.2705 0.030 Uiso 1 1 calc R . .
C12A C 0.39856(4) 0.60362(4) 1.37896(9) 0.0244(3) Uani 1 1 d . . .
H12C H 0.4300 0.6449 1.3945 0.029 Uiso 1 1 calc R . .
H12D H 0.4014 0.5724 1.4614 0.029 Uiso 1 1 calc R . .
O1 O 0.11546(4) 0.57009(4) 0.78461(9) 0.0208(2) Uani 1 1 d R . .
C2 C 0.15198(4) 0.62316(4) 0.86949(9) 0.0256(4) Uani 1 1 d R . .
H2A H 0.1530 0.6074 0.9674 0.031 Uiso 1 1 calc R . .
H2B H 0.1261 0.6689 0.8650 0.031 Uiso 1 1 calc R . .
C3 C 0.22765(9) 0.63336(8) 0.8169(2) 0.0273(4) Uani 1 1 d . . .
H3A H 0.2270 0.6387 0.7147 0.033 Uiso 1 1 calc R . .
H3B H 0.2476 0.6775 0.8570 0.033 Uiso 1 1 calc R . .
O4 O 0.27289(6) 0.57318(6) 0.85433(13) 0.0242(2) Uani 1 1 d . . .
C5 C 0.29762(8) 0.52839(9) 0.74057(18) 0.0264(4) Uani 1 1 d . . .
H5A H 0.3443 0.5080 0.7658 0.032 Uiso 1 1 calc R . .
H5B H 0.3045 0.5583 0.6572 0.032 Uiso 1 1 calc R . .
C6 C 0.24680(8) 0.46766(9) 0.70463(17) 0.0227(3) Uani 1 1 d . . .
H6A H 0.2003 0.4872 0.6756 0.027 Uiso 1 1 calc R . .
H6B H 0.2663 0.4393 0.6270 0.027 Uiso 1 1 calc R . .
O7 O 0.23783(6) 0.42260(6) 0.82720(13) 0.0250(2) Uani 1 1 d . . .
C8 C 0.19291(10) 0.36084(9) 0.8036(2) 0.0309(4) Uani 1 1 d . . .
H8A H 0.2086 0.3218 0.8653 0.037 Uiso 1 1 calc R . .
H8B H 0.1989 0.3447 0.7066 0.037 Uiso 1 1 calc R . .
C9 C 0.11397(9) 0.37589(9) 0.83018(19) 0.0272(4) Uani 1 1 d . . .
H9A H 0.0870 0.3307 0.8299 0.033 Uiso 1 1 calc R . .
H9B H 0.1080 0.3984 0.9223 0.033 Uiso 1 1 calc R . .
O10 O 0.08656(6) 0.42312(6) 0.72201(12) 0.0236(2) Uani 1 1 d . . .
C11 C 0.03184(8) 0.47235(9) 0.76738(19) 0.0266(3) Uani 1 1 d . . .
H11E H -0.0049 0.4458 0.8191 0.032 Uiso 1 1 calc R . .
H11F H 0.0090 0.4938 0.6848 0.032 Uiso 1 1 calc R . .
C12 C 0.06097(9) 0.53192(9) 0.86022(18) 0.0253(3) Uani 1 1 d . . .
H12E H 0.0222 0.5648 0.8864 0.030 Uiso 1 1 calc R . .
H12F H 0.0812 0.5114 0.9462 0.030 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S11G 0.02275(19) 0.02916(19) 0.01572(18) 0.00542(15) -0.00584(16) -0.00592(15)
S12G 0.02277(19) 0.02462(18) 0.01317(17) -0.00063(14) -0.00382(15) 0.00337(15)
N11G 0.0230(7) 0.0322(7) 0.0175(7) 0.0068(6) -0.0045(6) -0.0085(6)
C11G 0.0197(7) 0.0197(7) 0.0130(7) -0.0009(5) -0.0008(6) 0.0016(6)
N12G 0.0178(6) 0.0240(7) 0.0124(6) 0.0032(5) -0.0036(5) -0.0015(5)
C12G 0.0166(7) 0.0181(6) 0.0150(7) 0.0018(5) -0.0005(6) -0.0033(6)
N13G 0.0188(6) 0.0254(7) 0.0113(6) -0.0024(5) -0.0019(5) 0.0031(5)
N14G 0.0244(7) 0.0338(8) 0.0146(7) -0.0018(6) -0.0026(6) 0.0107(6)
S1G 0.02394(19) 0.0283(2) 0.01439(18) -0.00339(15) 0.00613(16) -0.00607(15)
S2G 0.02485(19) 0.02721(19) 0.01491(18) 0.00399(15) 0.00668(16) 0.00723(16)
N1G 0.0242(7) 0.0334(8) 0.0161(7) -0.0062(6) 0.0055(6) -0.0099(6)
C1G 0.0201(7) 0.0164(7) 0.0156(7) 0.0001(5) 0.0016(6) 0.0016(6)
N2G 0.0177(6) 0.0245(6) 0.0118(6) -0.0014(5) 0.0024(5) -0.0029(5)
C2G 0.0160(7) 0.0187(7) 0.0148(7) -0.0017(5) 0.0027(6) -0.0018(6)
N3G 0.0188(6) 0.0249(7) 0.0115(6) 0.0022(5) 0.0026(5) 0.0022(5)
N4G 0.0196(7) 0.0333(8) 0.0142(7) 0.0033(6) 0.0038(6) 0.0077(6)
O1A 0.0203(5) 0.0266(5) 0.0169(6) 0.0017(4) 0.0022(4) -0.0010(4)
C2A 0.0172(7) 0.0308(8) 0.0236(8) -0.0011(7) -0.0007(6) 0.0021(6)
C3A 0.0256(7) 0.0287(8) 0.0211(8) 0.0012(6) -0.0090(7) 0.0041(7)
O4A 0.0196(5) 0.0254(5) 0.0161(6) -0.0012(4) -0.0006(4) -0.0006(4)
C5A 0.0286(8) 0.0213(8) 0.0289(9) 0.0011(7) 0.0032(7) -0.0006(6)
C6A 0.0270(8) 0.0239(8) 0.0317(10) -0.0074(7) 0.0039(7) -0.0036(6)
O7A 0.0229(5) 0.0239(6) 0.0242(6) -0.0030(5) 0.0067(5) -0.0026(4)
C8A 0.0187(7) 0.0298(8) 0.0278(9) -0.0026(7) -0.0023(7) 0.0008(6)
C9A 0.0196(7) 0.0253(7) 0.0186(7) 0.0011(6) 0.0000(6) 0.0029(6)
O10A 0.0217(5) 0.0234(6) 0.0186(6) -0.0011(4) 0.0017(5) -0.0024(4)
C11A 0.0292(8) 0.0185(7) 0.0269(9) -0.0011(6) 0.0033(7) -0.0026(6)
C12A 0.0237(8) 0.0283(8) 0.0213(8) -0.0037(6) 0.0013(6) -0.0054(7)
O1 0.0221(5) 0.0243(5) 0.0159(6) -0.0003(4) 0.0009(5) -0.0003(4)
C2 0.0309(9) 0.0238(8) 0.0221(9) -0.0052(7) -0.0035(7) 0.0035(7)
C3 0.0306(8) 0.0215(8) 0.0296(9) 0.0010(7) -0.0073(8) -0.0036(7)
O4 0.0240(6) 0.0271(6) 0.0215(6) 0.0005(5) -0.0050(5) -0.0012(5)
C5 0.0189(7) 0.0349(9) 0.0254(9) 0.0011(7) 0.0024(6) 0.0003(7)
C6 0.0217(7) 0.0280(8) 0.0184(8) -0.0023(6) -0.0004(6) 0.0031(6)
O7 0.0259(6) 0.0248(6) 0.0243(6) 0.0008(5) -0.0063(5) 0.0006(5)
C8 0.0397(10) 0.0188(7) 0.0340(11) -0.0021(7) -0.0060(8) 0.0025(7)
C9 0.0347(9) 0.0237(7) 0.0233(8) 0.0023(7) -0.0042(8) -0.0084(7)
O10 0.0254(5) 0.0280(6) 0.0174(6) -0.0030(4) -0.0002(5) -0.0032(5)
C11 0.0181(7) 0.0362(9) 0.0255(9) 0.0009(7) 0.0015(7) -0.0023(7)
C12 0.0252(7) 0.0293(8) 0.0215(8) 0.0006(7) 0.0063(7) 0.0025(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11G C11G 1.6952(16) . ?
S12G C12G 1.6973(16) . ?
N11G C11G 1.319(2) . ?
N11G H1N 0.88(2) . ?
N11G H2N 0.89(2) . ?
C11G N12G 1.360(2) . ?
N12G N13G 1.3975(18) . ?
N12G H3N 0.898(18) . ?
C12G N14G 1.324(2) . ?
C12G N13G 1.3466(19) . ?
N13G H4N 0.871(19) . ?
N14G H5N 0.888(19) . ?
N14G H6N 0.91(2) . ?
S1G C1G 1.6965(16) . ?
S2G C2G 1.6921(16) . ?
N1G C1G 1.318(2) . ?
N1G H7N 0.89(2) . ?
N1G H8N 0.92(2) . ?
C1G N2G 1.3636(19) . ?
N2G N3G 1.3952(18) . ?
N2G H9N 0.915(19) . ?
C2G N4G 1.323(2) . ?
C2G N3G 1.3563(19) . ?
N3G H10N 0.90(2) . ?
N4G H11N 0.82(2) . ?
N4G H12N 0.797(19) . ?
O1A C2A 1.4319(18) . ?
O1A C12A 1.4346(14) . ?
C2A C3A 1.505(2) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A O4A 1.4223(19) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
O4A C5A 1.4292(19) . ?
C5A C6A 1.503(2) . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A O7A 1.4307(19) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
O7A C8A 1.436(2) . ?
C8A C9A 1.497(2) . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A O10A 1.4372(19) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
O10A C11A 1.4343(18) . ?
C11A C12A 1.5022(18) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
O1 C12 1.4209(18) . ?
O1 C2 1.4338 . ?
C2 C3 1.4956(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O4 1.4339(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O4 C5 1.430(2) . ?
C5 C6 1.500(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O7 1.4345(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C8 1.4269(19) . ?
C8 C9 1.506(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O10 1.435(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O10 C11 1.4249(19) . ?
C11 C12 1.505(2) . ?
C11 H11E 0.9700 . ?
C11 H11F 0.9700 . ?
C12 H12E 0.9700 . ?
C12 H12F 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11G N11G H1N 120.0(14) . . ?
C11G N11G H2N 120.7(13) . . ?
H1N N11G H2N 119.3(18) . . ?
N11G C11G N12G 118.12(14) . . ?
N11G C11G S11G 122.75(12) . . ?
N12G C11G S11G 119.11(12) . . ?
C11G N12G N13G 118.77(13) . . ?
C11G N12G H3N 119.9(11) . . ?
N13G N12G H3N 114.5(12) . . ?
N14G C12G N13G 118.71(14) . . ?
N14G C12G S12G 122.71(12) . . ?
N13G C12G S12G 118.57(12) . . ?
C12G N13G N12G 121.42(14) . . ?
C12G N13G H4N 123.7(12) . . ?
N12G N13G H4N 113.0(12) . . ?
C12G N14G H5N 118.3(13) . . ?
C12G N14G H6N 123.9(13) . . ?
H5N N14G H6N 117.8(18) . . ?
C1G N1G H7N 120.7(13) . . ?
C1G N1G H8N 120.5(12) . . ?
H7N N1G H8N 117.9(17) . . ?
N1G C1G N2G 118.49(14) . . ?
N1G C1G S1G 122.59(12) . . ?
N2G C1G S1G 118.89(12) . . ?
C1G N2G N3G 119.48(13) . . ?
C1G N2G H9N 120.3(12) . . ?
N3G N2G H9N 114.0(13) . . ?
N4G C2G N3G 118.15(14) . . ?
N4G C2G S2G 122.59(12) . . ?
N3G C2G S2G 119.25(12) . . ?
C2G N3G N2G 120.76(13) . . ?
C2G N3G H10N 122.0(13) . . ?
N2G N3G H10N 113.5(13) . . ?
C2G N4G H11N 120.8(14) . . ?
C2G N4G H12N 117.8(14) . . ?
H11N N4G H12N 121.0(19) . . ?
C2A O1A C12A 114.91(11) . . ?
O1A C2A C3A 112.73(12) . . ?
O1A C2A H2A1 109.0 . . ?
C3A C2A H2A1 109.0 . . ?
O1A C2A H2A2 109.0 . . ?
C3A C2A H2A2 109.0 . . ?
H2A1 C2A H2A2 107.8 . . ?
O4A C3A C2A 108.95(13) . . ?
O4A C3A H3A1 109.9 . . ?
C2A C3A H3A1 109.9 . . ?
O4A C3A H3A2 109.9 . . ?
C2A C3A H3A2 109.9 . . ?
H3A1 C3A H3A2 108.3 . . ?
C3A O4A C5A 113.61(13) . . ?
O4A C5A C6A 109.63(13) . . ?
O4A C5A H5A1 109.7 . . ?
C6A C5A H5A1 109.7 . . ?
O4A C5A H5A2 109.7 . . ?
C6A C5A H5A2 109.7 . . ?
H5A1 C5A H5A2 108.2 . . ?
O7A C6A C5A 111.55(14) . . ?
O7A C6A H6A1 109.3 . . ?
C5A C6A H6A1 109.3 . . ?
O7A C6A H6A2 109.3 . . ?
C5A C6A H6A2 109.3 . . ?
H6A1 C6A H6A2 108.0 . . ?
C6A O7A C8A 116.51(13) . . ?
O7A C8A C9A 113.38(12) . . ?
O7A C8A H8A1 108.9 . . ?
C9A C8A H8A1 108.9 . . ?
O7A C8A H8A2 108.9 . . ?
C9A C8A H8A2 108.9 . . ?
H8A1 C8A H8A2 107.7 . . ?
O10A C9A C8A 109.15(13) . . ?
O10A C9A H9A1 109.9 . . ?
C8A C9A H9A1 109.9 . . ?
O10A C9A H9A2 109.9 . . ?
C8A C9A H9A2 109.9 . . ?
H9A1 C9A H9A2 108.3 . . ?
C11A O10A C9A 113.01(12) . . ?
O10A C11A C12A 113.23(12) . . ?
O10A C11A H11C 108.9 . . ?
C12A C11A H11C 108.9 . . ?
O10A C11A H11D 108.9 . . ?
C12A C11A H11D 108.9 . . ?
H11C C11A H11D 107.7 . . ?
O1A C12A C11A 109.69(10) . . ?
O1A C12A H12C 109.7 . . ?
C11A C12A H12C 109.7 . . ?
O1A C12A H12D 109.7 . . ?
C11A C12A H12D 109.7 . . ?
H12C C12A H12D 108.2 . . ?
C12 O1 C2 113.00(8) . . ?
O1 C2 C3 109.88(8) . . ?
O1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
O1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O4 C3 C2 111.44(12) . . ?
O4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
O4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 O4 C3 116.62(13) . . ?
O4 C5 C6 113.66(13) . . ?
O4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
O4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O7 C6 C5 108.80(13) . . ?
O7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C8 O7 C6 113.81(13) . . ?
O7 C8 C9 112.97(13) . . ?
O7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
O7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O10 C9 C8 109.58(14) . . ?
O10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
O10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C11 O10 C9 115.05(13) . . ?
O10 C11 C12 112.74(13) . . ?
O10 C11 H11E 109.0 . . ?
C12 C11 H11E 109.0 . . ?
O10 C11 H11F 109.0 . . ?
C12 C11 H11F 109.0 . . ?
H11E C11 H11F 107.8 . . ?
O1 C12 C11 108.81(13) . . ?
O1 C12 H12E 109.9 . . ?
C11 C12 H12E 109.9 . . ?
O1 C12 H12F 109.9 . . ?
C11 C12 H12F 109.9 . . ?
H12E C12 H12F 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O4 -74.04(13) . . . . ?
C2 C3 O4 C5 112.00(15) . . . . ?
C3 O4 C5 C6 -88.43(17) . . . . ?
O4 C5 C6 O7 -59.69(17) . . . . ?
C5 C6 O7 C8 -177.32(12) . . . . ?
C6 O7 C8 C9 -88.77(18) . . . . ?
O7 C8 C9 O10 69.83(18) . . . . ?
C8 C9 O10 C11 -146.65(13) . . . . ?
C9 O10 C11 C12 71.77(17) . . . . ?
O10 C11 C12 O1 58.00(18) . . . . ?
C11 C12 O1 C2 -173.80(9) . . . . ?
C12 O1 C2 C3 151.22(12) . . . . ?
O1A C2A C3A O4A 59.88(17) . . . . ?
C2A C3A O4A C5A -173.04(12) . . . . ?
C3A O4A C5A C6A 148.24(13) . . . . ?
O4A C5A C6A O7A -76.00(17) . . . . ?
C5A C6A O7A C8A 113.06(15) . . . . ?
C6A O7A C8A C9A -87.52(17) . . . . ?
O7A C8A C9A O10A -61.76(17) . . . . ?
C8A C9A O10A C11A -176.32(12) . . . . ?
C9A O10A C11A C12A -87.93(15) . . . . ?
O10A C11A C12A O1A 68.55(15) . . . . ?
C11A C12A O1A C2A -146.02(11) . . . . ?
C12A O1A C2A C3A 73.55(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1G H7N O7A 0.89(2) 1.95(2) 2.8327(19) 170.6(19) 3_567
N1G H8N O10 0.92(2) 1.99(2) 2.8416(19) 152.9(17) 3_566
N2G H9N S2G 0.915(19) 2.372(18) 3.2749(15) 169.0(17) 4_576
N3G H10N S1G 0.90(2) 2.36(2) 3.2517(15) 169.8(18) 4_575
N4G H11N O1 0.82(2) 2.19(2) 2.9758(18) 161.4(18) .
N4G H12N O10A 0.797(19) 2.200(19) 2.991(2) 171.5(18) 1_554
N11G H1N O4 0.88(2) 1.99(2) 2.8597(19) 170(2) .
N11G H2N O1A 0.89(2) 2.02(2) 2.8644(19) 157.5(17) .
N12G H3N S12G 0.898(18) 2.440(18) 3.3255(15) 169.1(16) 4_575
N13G H4N S11G 0.871(19) 2.374(19) 3.2354(15) 169.7(17) 4_576
N14G H5N O7 0.888(19) 2.08(2) 2.9533(19) 169.7(17) 3_667
N14G H6N O4A 0.91(2) 2.08(2) 2.9548(19) 160.7(18) 3_667

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.058