# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2004

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Dr Andrew Whiting'
_publ_contact_author_address     
;
Chemistry
University of Durham
South Road
Durham
DH1 3QZ
UNITED KINGDOM
;

_publ_contact_author_email       ANDY.WHITING@DURHAM.AC.UK

_publ_section_title              
;
Mechanistic Studies on the Aza-Diels-Alder
Reactions of N-Aryl Imines: Evidence for the Non-concertedness under
Lewis-acid Catalysed Conditions.
;
_publ_requested_category         FO
loop_
_publ_author_name
'Andrew Whiting'
'Stephen Hermitage'
'Judith A.K. Howard'
'David Jay'
'Robin Gavin Pritchard'
;
M.R.Probert
;

data_02srv184
_database_code_depnum_ccdc_archive 'CCDC 237030'

_chemical_name_systematic        
;
?
;
_chemical_name_common            
;
Ethyl-5-acetyl-8-methoxy-3a,4,5,9b-tetrahydro-3H-
cyclopenta(c)quinoline -4-carboxylate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.2885(4)
_cell_length_b                   9.7175(4)
_cell_length_c                   10.1841(5)
_cell_angle_alpha                67.610(2)
_cell_angle_beta                 83.860(2)
_cell_angle_gamma                66.887(2)
_cell_volume                     780.73(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2649
_cell_measurement_theta_min      2.367
_cell_measurement_theta_max      29.979

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale orange'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  .
_exptl_absorpt_correction_T_max  .
_exptl_absorpt_process_details   none

_exptl_special_details           
;
The data collection nominally covered full sphere
of reciprocal Space, by a combination of 4 sets of \w scans
each set at different \f and/or 2\q angles and each
scan (10s exposure) covering 0.3\% in \w. Crystal to
detector distance 4.85 cm.
;

_diffrn_ambient_temperature      120(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  'Bruker SMART CCD 6K area detector'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean 8
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            7014
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.01
_reflns_number_total             4517
_reflns_number_gt                3097
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART-NT V5.0 (Bruker, 1998)'
_computing_cell_refinement       'SMART-NT V5.0 (Bruker, 1998)'
_computing_data_reduction        'SMART-NT V5.0 (Bruker, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0811P)^2^+0.0000P] 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         4517
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1329
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_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 0.49036(12) 0.32942(13) 1.18180(11) 0.0277(2) Uani 1 1 d . . .
O2 O 0.84164(13) 0.25104(12) 0.72193(11) 0.0260(2) Uani 1 1 d . . .
O3 O 0.88362(13) 0.18649(12) 0.52777(11) 0.0267(2) Uani 1 1 d . . .
N1 N 0.83279(14) -0.05876(13) 0.87924(12) 0.0204(3) Uani 1 1 d . . .
O4 O 0.99646(14) -0.29090(12) 0.85594(12) 0.0305(3) Uani 1 1 d . . .
C5 C 0.74131(16) 0.03551(16) 0.96011(14) 0.0191(3) Uani 1 1 d . . .
C7 C 0.50021(16) 0.23851(16) 0.98694(15) 0.0204(3) Uani 1 1 d . . .
H7A H 0.3947 0.3089 0.9562 0.025 Uiso 1 1 calc R . .
C6 C 0.58766(16) 0.13960(16) 0.91270(14) 0.0191(3) Uani 1 1 d . . .
C3 C 0.72074(16) 0.13111(17) 1.15057(15) 0.0217(3) Uani 1 1 d . . .
H3A H 0.7661 0.1274 1.2318 0.026 Uiso 1 1 calc R . .
C4 C 0.80797(16) 0.03386(16) 1.07781(15) 0.0203(3) Uani 1 1 d . . .
H4A H 0.9141 -0.0347 1.1079 0.024 Uiso 1 1 calc R . .
C12 C 0.62530(17) 0.05033(17) 0.69778(15) 0.0223(3) Uani 1 1 d . . .
H12A H 0.6129 -0.0551 0.7294 0.027 Uiso 1 1 calc R . .
C2 C 0.56631(16) 0.23470(16) 1.10518(15) 0.0213(3) Uani 1 1 d . . .
C8 C 0.51458(16) 0.15168(16) 0.78077(15) 0.0213(3) Uani 1 1 d . . .
H8A H 0.4249 0.1158 0.8102 0.026 Uiso 1 1 calc R . .
C14 C 0.84167(16) 0.16581(17) 0.66185(14) 0.0209(3) Uani 1 1 d . . .
C13 C 0.79834(17) 0.01844(16) 0.72490(14) 0.0214(3) Uani 1 1 d . . .
H13A H 0.8652 -0.0610 0.6816 0.026 Uiso 1 1 calc R . .
C17 C 0.92295(16) -0.22098(16) 0.93431(15) 0.0216(3) Uani 1 1 d . . .
C18 C 0.92833(17) -0.31237(17) 1.09219(15) 0.0239(3) Uani 1 1 d . . .
H18A H 0.9971 -0.4257 1.1146 0.036 Uiso 0.50 1 calc PR . .
H18B H 0.8225 -0.3048 1.1220 0.036 Uiso 0.50 1 calc PR . .
H18C H 0.9689 -0.2660 1.1427 0.036 Uiso 0.50 1 calc PR . .
H18D H 0.8619 -0.2386 1.1382 0.036 Uiso 0.50 1 calc PR . .
H18E H 1.0365 -0.3596 1.1309 0.036 Uiso 0.50 1 calc PR . .
H18F H 0.8900 -0.3983 1.1102 0.036 Uiso 0.50 1 calc PR . .
C11 C 0.56537(19) 0.14836(18) 0.54054(16) 0.0268(3) Uani 1 1 d . . .
H11A H 0.6535 0.1423 0.4762 0.032 Uiso 1 1 calc R . .
H11B H 0.4938 0.1096 0.5129 0.032 Uiso 1 1 calc R . .
C9 C 0.45277(18) 0.31933(17) 0.66714(16) 0.0260(3) Uani 1 1 d . . .
H9A H 0.4006 0.4149 0.6866 0.031 Uiso 1 1 calc R . .
C15 C 0.9271(2) 0.32499(19) 0.45252(16) 0.0295(3) Uani 1 1 d . . .
H15A H 0.8579 0.4168 0.4792 0.035 Uiso 1 1 calc R . .
H15B H 0.9114 0.3572 0.3488 0.035 Uiso 1 1 calc R . .
C1 C 0.33243(18) 0.43996(18) 1.13710(18) 0.0287(3) Uani 1 1 d . . .
H1A H 0.2922 0.4999 1.2006 0.043 Uiso 1 1 calc R . .
H1B H 0.2672 0.3803 1.1405 0.043 Uiso 1 1 calc R . .
H1C H 0.3297 0.5155 1.0396 0.043 Uiso 1 1 calc R . .
C10 C 0.47994(19) 0.31707(18) 0.53788(16) 0.0286(3) Uani 1 1 d . . .
H10A H 0.4493 0.4107 0.4533 0.034 Uiso 1 1 calc R . .
C16 C 1.0949(2) 0.2873(2) 0.4870(2) 0.0371(4) Uani 1 1 d . . .
H16A H 1.1201 0.3824 0.4349 0.056 Uiso 1 1 calc R . .
H16B H 1.1637 0.1977 0.4591 0.056 Uiso 1 1 calc R . .
H16C H 1.1102 0.2573 0.5894 0.056 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
O1 0.0249(6) 0.0285(5) 0.0291(6) -0.0175(5) 0.0014(4) -0.0030(4)
O2 0.0331(6) 0.0266(5) 0.0231(5) -0.0118(4) 0.0050(4) -0.0145(4)
O3 0.0375(6) 0.0267(5) 0.0204(5) -0.0110(4) 0.0078(4) -0.0161(5)
N1 0.0219(6) 0.0180(5) 0.0193(6) -0.0077(4) 0.0018(4) -0.0049(4)
O4 0.0372(6) 0.0213(5) 0.0287(6) -0.0116(4) 0.0055(5) -0.0056(4)
C5 0.0200(7) 0.0164(6) 0.0196(6) -0.0063(5) 0.0030(5) -0.0063(5)
C7 0.0179(7) 0.0176(6) 0.0227(7) -0.0056(5) 0.0012(5) -0.0054(5)
C6 0.0204(7) 0.0176(6) 0.0191(6) -0.0055(5) 0.0006(5) -0.0083(5)
C3 0.0230(7) 0.0228(7) 0.0195(6) -0.0081(5) 0.0006(5) -0.0087(5)
C4 0.0187(7) 0.0193(6) 0.0202(6) -0.0056(5) 0.0007(5) -0.0062(5)
C12 0.0278(7) 0.0193(6) 0.0212(7) -0.0072(5) 0.0003(5) -0.0106(6)
C2 0.0227(7) 0.0200(6) 0.0218(7) -0.0090(5) 0.0047(5) -0.0084(5)
C8 0.0210(7) 0.0212(6) 0.0213(7) -0.0060(5) -0.0012(5) -0.0088(5)
C14 0.0204(7) 0.0219(6) 0.0187(6) -0.0079(5) 0.0013(5) -0.0061(5)
C13 0.0261(7) 0.0200(6) 0.0179(6) -0.0075(5) 0.0009(5) -0.0082(5)
C17 0.0206(7) 0.0198(6) 0.0248(7) -0.0085(5) 0.0015(5) -0.0081(5)
C18 0.0247(7) 0.0193(6) 0.0232(7) -0.0057(5) -0.0008(5) -0.0057(5)
C11 0.0329(8) 0.0276(7) 0.0228(7) -0.0093(6) -0.0033(6) -0.0133(6)
C9 0.0278(8) 0.0210(7) 0.0258(7) -0.0067(6) -0.0050(6) -0.0061(6)
C15 0.0417(9) 0.0264(7) 0.0224(7) -0.0078(6) 0.0083(6) -0.0179(7)
C1 0.0235(8) 0.0259(7) 0.0345(8) -0.0148(6) 0.0038(6) -0.0044(6)
C10 0.0343(8) 0.0255(7) 0.0245(7) -0.0045(6) -0.0049(6) -0.0131(6)
C16 0.0395(10) 0.0410(9) 0.0402(10) -0.0207(8) 0.0133(8) -0.0220(8)

_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 1.3687(16) . ?
O1 C1 1.4304(18) . ?
O2 C14 1.2026(17) . ?
O3 C14 1.3398(17) . ?
O3 C15 1.4618(18) . ?
N1 C17 1.3753(17) . ?
N1 C5 1.4330(17) . ?
N1 C13 1.4685(18) . ?
O4 C17 1.2235(17) . ?
C5 C6 1.3911(19) . ?
C5 C4 1.3988(19) . ?
C7 C2 1.391(2) . ?
C7 C6 1.4016(19) . ?
C7 H7A 0.9500 . ?
C6 C8 1.5140(19) . ?
C3 C4 1.3793(18) . ?
C3 C2 1.3922(19) . ?
C3 H3A 0.9500 . ?
C4 H4A 0.9500 . ?
C12 C11 1.547(2) . ?
C12 C13 1.547(2) . ?
C12 C8 1.5475(19) . ?
C12 H12A 1.0000 . ?
C8 C9 1.5147(19) . ?
C8 H8A 1.0000 . ?
C14 C13 1.524(2) . ?
C13 H13A 1.0000 . ?
C17 C18 1.507(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 0.9800 . ?
C11 C10 1.506(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C9 C10 1.320(2) . ?
C9 H9A 0.9500 . ?
C15 C16 1.502(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 H10A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 C1 117.78(11) . . ?
C14 O3 C15 116.12(11) . . ?
C17 N1 C5 125.44(11) . . ?
C17 N1 C13 117.85(11) . . ?
C5 N1 C13 115.30(11) . . ?
C6 C5 C4 120.04(12) . . ?
C6 C5 N1 118.72(12) . . ?
C4 C5 N1 121.03(12) . . ?
C2 C7 C6 120.68(12) . . ?
C2 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C5 C6 C7 119.04(12) . . ?
C5 C6 C8 121.55(12) . . ?
C7 C6 C8 119.39(12) . . ?
C4 C3 C2 120.09(13) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.47(13) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C11 C12 C13 113.79(12) . . ?
C11 C12 C8 104.78(11) . . ?
C13 C12 C8 111.03(11) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C8 C12 H12A 109.0 . . ?
O1 C2 C7 124.42(12) . . ?
O1 C2 C3 115.92(12) . . ?
C7 C2 C3 119.65(13) . . ?
C6 C8 C9 114.64(11) . . ?
C6 C8 C12 115.58(11) . . ?
C9 C8 C12 102.39(11) . . ?
C6 C8 H8A 107.9 . . ?
C9 C8 H8A 107.9 . . ?
C12 C8 H8A 107.9 . . ?
O2 C14 O3 123.99(13) . . ?
O2 C14 C13 126.16(13) . . ?
O3 C14 C13 109.83(11) . . ?
N1 C13 C14 111.14(11) . . ?
N1 C13 C12 107.52(11) . . ?
C14 C13 C12 115.32(11) . . ?
N1 C13 H13A 107.5 . . ?
C14 C13 H13A 107.5 . . ?
C12 C13 H13A 107.5 . . ?
O4 C17 N1 120.46(13) . . ?
O4 C17 C18 120.29(12) . . ?
N1 C17 C18 119.24(12) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C17 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C10 C11 C12 102.88(12) . . ?
C10 C11 H11A 111.2 . . ?
C12 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C12 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
C10 C9 C8 112.06(13) . . ?
C10 C9 H9A 124.0 . . ?
C8 C9 H9A 124.0 . . ?
O3 C15 C16 111.56(13) . . ?
O3 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O3 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 C11 111.92(13) . . ?
C9 C10 H10A 124.0 . . ?
C11 C10 H10A 124.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.056

#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2004-04-23 at 12:47:50
#  Using CIFtbx version 2.6.2 16 Jun 1998

#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.2
#  Request file    : c:\wingx\files\archive.dat
#  CIF files read  : a dreduc psi_scan struct

data_a
_database_code_depnum_ccdc_archive 'CCDC 237039'

_audit_creation_date             2004-04-23T12:47:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C17 H19 N1 O5'
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   7.959(14)
_cell_length_b                   16.440(14)
_cell_length_c                   12.342(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.010(10)
_cell_angle_gamma                90
_cell_volume                     1615(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      16.3
_cell_measurement_theta_max      53.2
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   3
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_absorpt_correction_T_min  0.8695
_exptl_absorpt_correction_T_max  0.9599

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_measurement_device       'Eulerian-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC6S'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 -1 0
3 -1 -3
-1 1 -5

_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_number            5069
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.48
_diffrn_reflns_theta_max         60.76
_diffrn_reflns_theta_full        60.76
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_reflns_number_total             2397
_reflns_number_gt                1602
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1991)
;
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_reduction        
'teXsan (Molecular Structure Corporation, 1999)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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^)+(0.1019P)^2^+0.0000P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.0373(18)
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1564
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.95267(18) 0.62775(9) 0.53294(15) 0.0893(6) Uani 1 1 d . . .
O2 O 0.75015(15) 0.71542(7) 0.57406(10) 0.0550(4) Uani 1 1 d . . .
O3A O 0.7437(4) 0.21979(16) 0.5541(2) 0.0649(8) Uani 0.5 1 d P A .
O4 O 0.5528(2) 0.17631(10) 0.67435(14) 0.0851(5) Uani 1 1 d . A .
O5 O 0.11818(16) 0.36479(8) 0.79734(12) 0.0645(4) Uani 1 1 d . . .
N1 N 0.55891(18) 0.59644(9) 0.65006(13) 0.0500(4) Uani 1 1 d . . .
C2 C 0.6997(2) 0.57556(11) 0.60325(16) 0.0521(5) Uani 1 1 d . . .
C3A C 0.7645(5) 0.4968(3) 0.6110(4) 0.0534(12) Uani 0.5 1 d P . .
H3A H 0.8759 0.4875 0.5918 0.064 Uiso 0.5 1 calc PR . .
C4A C 0.6696(5) 0.4340(2) 0.6456(3) 0.0489(10) Uani 0.5 1 d P . .
C5 C 0.3804(2) 0.39290(11) 0.70831(17) 0.0591(6) Uani 1 1 d . . .
H5 H 0.405 0.3379 0.7004 0.071 Uiso 1 1 calc R A .
C6 C 0.2355(2) 0.41592(11) 0.75615(16) 0.0515(5) Uani 1 1 d . . .
C7 C 0.1960(3) 0.49825(13) 0.7659(2) 0.0703(6) Uani 1 1 d . . .
H7 H 0.0938 0.5133 0.7964 0.084 Uiso 1 1 calc R A .
C8 C 0.3030(2) 0.55638(12) 0.73194(18) 0.0652(6) Uani 1 1 d . . .
H8 H 0.2753 0.6109 0.741 0.078 Uiso 1 1 calc R . .
C9 C 0.4559(2) 0.53524(11) 0.68304(14) 0.0467(4) Uani 1 1 d . . .
C10 C 0.4945(2) 0.45193(11) 0.67025(17) 0.0566(5) Uani 1 1 d . A .
C11 C 0.8145(2) 0.64122(12) 0.56698(17) 0.0554(5) Uani 1 1 d . . .
C12 C 0.8589(3) 0.78137(12) 0.54304(18) 0.0645(6) Uani 1 1 d . . .
H12A H 0.9068 0.7707 0.4722 0.077 Uiso 1 1 calc R . .
H12B H 0.9502 0.7864 0.5947 0.077 Uiso 1 1 calc R . .
C13 C 0.7607(3) 0.85753(13) 0.5401(2) 0.0792(7) Uani 1 1 d . . .
H13A H 0.8328 0.9018 0.5199 0.119 Uiso 1 1 calc R . .
H13B H 0.7139 0.8678 0.6105 0.119 Uiso 1 1 calc R . .
H13C H 0.6717 0.8525 0.4881 0.119 Uiso 1 1 calc R . .
C15A C 0.7388(5) 0.3457(3) 0.6484(4) 0.0582(11) Uani 0.5 1 d P . .
H15A H 0.8607 0.3462 0.6467 0.07 Uiso 0.5 1 calc PR . .
H15B H 0.7026 0.3183 0.714 0.07 Uiso 0.5 1 calc PR . .
C16A C 0.6725(6) 0.3041(3) 0.5529(4) 0.0680(13) Uani 0.5 1 d P . .
H16A H 0.7059 0.3324 0.4874 0.082 Uiso 0.5 1 calc PR A .
H16B H 0.5507 0.3021 0.5556 0.082 Uiso 0.5 1 calc PR . .
C17 C 0.6755(3) 0.16238(12) 0.62172(19) 0.0653(6) Uani 1 1 d . . .
C18 C 0.7381(3) 0.08150(14) 0.5893(2) 0.0842(8) Uani 1 1 d . A .
H18A H 0.8391 0.0877 0.5476 0.126 Uiso 0.5 1 calc PR . .
H18B H 0.6545 0.0544 0.5465 0.126 Uiso 0.5 1 calc PR . .
H18C H 0.7616 0.0498 0.6529 0.126 Uiso 0.5 1 calc PR . .
H18D H 0.6643 0.0403 0.6171 0.126 Uiso 0.5 1 calc PR . .
H18E H 0.8489 0.0735 0.6182 0.126 Uiso 0.5 1 calc PR . .
H18F H 0.7418 0.0781 0.5117 0.126 Uiso 0.5 1 calc PR . .
C19 C 0.1497(3) 0.27952(12) 0.79038(19) 0.0680(6) Uani 1 1 d . . .
H19A H 0.1672 0.2647 0.716 0.102 Uiso 1 1 calc R . .
H19B H 0.0551 0.2502 0.8186 0.102 Uiso 1 1 calc R . .
H19C H 0.2481 0.2663 0.8318 0.102 Uiso 1 1 calc R . .
O3B O 0.8006(3) 0.21903(15) 0.6156(2) 0.0481(7) Uani 0.5 1 d P A 1
C3B C 0.7300(5) 0.4935(3) 0.5641(3) 0.0420(10) Uani 0.5 1 d P A 1
H3B H 0.8215 0.4831 0.5193 0.05 Uiso 0.5 1 calc PR A 1
C4B C 0.6251(5) 0.4318(2) 0.5926(3) 0.0380(9) Uani 0.5 1 d P A 1
C15B C 0.6644(5) 0.3474(2) 0.5614(3) 0.0405(9) Uani 0.5 1 d P A 1
H15C H 0.7312 0.3483 0.4957 0.049 Uiso 0.5 1 calc PR A 1
H15D H 0.5602 0.3194 0.545 0.049 Uiso 0.5 1 calc PR A 1
C16B C 0.7606(5) 0.2984(2) 0.6489(3) 0.0469(10) Uani 0.5 1 d P A 1
H16C H 0.8636 0.327 0.6669 0.056 Uiso 0.5 1 calc PR A 1
H16D H 0.6925 0.2957 0.714 0.056 Uiso 0.5 1 calc PR A 1

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 0.0617(9) 0.0605(9) 0.1457(15) 0.0026(9) 0.0541(10) 0.0022(7)
O2 0.0464(7) 0.0432(7) 0.0755(8) 0.0037(6) 0.0168(6) -0.0031(6)
O3A 0.0632(17) 0.0435(15) 0.088(2) -0.0063(15) 0.0236(16) 0.0051(13)
O4 0.0683(9) 0.0774(11) 0.1094(12) 0.0022(9) 0.0316(9) -0.0097(8)
O5 0.0493(7) 0.0487(7) 0.0957(10) 0.0060(7) 0.0226(7) -0.0063(6)
N1 0.0457(8) 0.0414(8) 0.0629(9) 0.0013(7) 0.0145(7) 0.0005(7)
C2 0.0459(9) 0.0442(10) 0.0662(12) 0.0016(9) 0.0168(9) 0.0034(8)
C3A 0.043(2) 0.051(2) 0.066(3) -0.003(2) 0.020(2) 0.0062(18)
C4A 0.047(2) 0.0360(19) 0.064(2) 0.0003(18) 0.0144(19) 0.0124(16)
C5 0.0549(11) 0.0389(9) 0.0834(14) 0.0033(9) 0.0212(10) 0.0041(8)
C6 0.0422(9) 0.0452(10) 0.0673(12) 0.0042(9) 0.0095(9) -0.0044(8)
C7 0.0503(10) 0.0530(11) 0.1076(16) 0.0029(11) 0.0331(11) 0.0038(9)
C8 0.0550(11) 0.0396(10) 0.1010(16) -0.0015(10) 0.0321(11) 0.0053(9)
C9 0.0433(9) 0.0412(9) 0.0556(10) 0.0012(8) 0.0111(8) 0.0012(8)
C10 0.0481(10) 0.0388(10) 0.0828(13) 0.0028(9) 0.0240(10) 0.0048(8)
C11 0.0491(10) 0.0478(10) 0.0693(12) 0.0011(9) 0.0192(9) 0.0018(9)
C12 0.0585(11) 0.0526(11) 0.0823(14) 0.0032(10) 0.0217(10) -0.0115(9)
C13 0.0804(15) 0.0519(12) 0.1054(18) 0.0177(12) 0.0190(13) 0.0004(12)
C15A 0.046(2) 0.068(3) 0.061(2) 0.002(2) 0.0116(19) 0.006(2)
C16A 0.065(3) 0.065(3) 0.074(3) 0.003(2) 0.013(2) 0.007(3)
C17 0.0646(13) 0.0472(11) 0.0840(14) 0.0010(11) 0.0133(11) -0.0040(10)
C18 0.0938(17) 0.0509(12) 0.1079(19) 0.0021(13) 0.0070(15) 0.0039(13)
C19 0.0620(13) 0.0490(11) 0.0932(16) 0.0126(11) 0.0088(11) -0.0091(10)
O3B 0.0399(13) 0.0399(13) 0.0644(17) 0.0045(13) 0.0005(12) 0.0069(11)
C3B 0.044(2) 0.045(2) 0.036(2) -0.0038(17) 0.0072(18) 0.0054(17)
C4B 0.0385(19) 0.042(2) 0.0330(19) 0.0008(16) -0.0038(16) 0.0027(16)
C15B 0.0430(19) 0.036(2) 0.043(2) -0.0036(17) 0.0059(16) 0.0046(18)
C16B 0.047(2) 0.0291(19) 0.065(2) -0.0006(18) 0.0022(18) 0.0075(17)

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C11 1.198(3) . ?
O2 C11 1.326(2) . ?
O2 C12 1.439(2) . ?
O3A C17 1.372(3) . ?
O3A C16A 1.497(5) . ?
O4 C17 1.195(3) . ?
O5 C6 1.355(2) . ?
O5 C19 1.427(3) . ?
N1 C2 1.307(3) . ?
N1 C9 1.360(2) . ?
C2 C3A 1.397(5) . ?
C2 C3B 1.453(5) . ?
C2 C11 1.484(3) . ?
C3A C4A 1.349(6) . ?
C3A H3A 0.93 . ?
C4A C10 1.457(5) . ?
C4A C15A 1.553(6) . ?
C5 C6 1.350(3) . ?
C5 C10 1.410(3) . ?
C5 H5 0.93 . ?
C6 C7 1.395(3) . ?
C7 C8 1.347(3) . ?
C7 H7 0.93 . ?
C8 C9 1.402(3) . ?
C8 H8 0.93 . ?
C9 C10 1.413(3) . ?
C10 C4B 1.452(4) . ?
C12 C13 1.476(3) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C15A C16A 1.462(7) . ?
C15A H15A 0.97 . ?
C15A H15B 0.97 . ?
C16A H16A 0.97 . ?
C16A H16B 0.97 . ?
C17 O3B 1.365(4) . ?
C17 C18 1.475(3) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C18 H18D 0.96 . ?
C18 H18E 0.96 . ?
C18 H18F 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
O3B C16B 1.405(4) . ?
C3B C4B 1.360(6) . ?
C3B H3B 0.93 . ?
C4B C15B 1.474(5) . ?
C15B C16B 1.550(6) . ?
C15B H15C 0.97 . ?
C15B H15D 0.97 . ?
C16B H16C 0.97 . ?
C16B H16D 0.97 . ?

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
C11 O2 C12 116.30(17) . . ?
C17 O3A C16A 119.5(3) . . ?
C6 O5 C19 117.74(17) . . ?
C2 N1 C9 117.05(17) . . ?
N1 C2 C3A 122.0(2) . . ?
N1 C2 C3B 122.2(2) . . ?
C3A C2 C3B 26.0(2) . . ?
N1 C2 C11 118.07(18) . . ?
C3A C2 C11 117.9(2) . . ?
C3B C2 C11 118.2(2) . . ?
C4A C3A C2 121.6(4) . . ?
C4A C3A H3A 119.2 . . ?
C2 C3A H3A 119.2 . . ?
C3A C4A C10 116.6(3) . . ?
C3A C4A C15A 121.6(4) . . ?
C10 C4A C15A 121.6(3) . . ?
C6 C5 C10 120.21(19) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
C5 C6 O5 125.37(19) . . ?
C5 C6 C7 120.16(18) . . ?
O5 C6 C7 114.47(18) . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.45(19) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N1 C9 C8 117.94(17) . . ?
N1 C9 C10 123.55(18) . . ?
C8 C9 C10 118.50(17) . . ?
C5 C10 C9 119.34(18) . . ?
C5 C10 C4B 121.6(2) . . ?
C9 C10 C4B 116.8(2) . . ?
C5 C10 C4A 123.2(2) . . ?
C9 C10 C4A 115.3(2) . . ?
C4B C10 C4A 29.64(18) . . ?
O1 C11 O2 123.23(18) . . ?
O1 C11 C2 122.47(19) . . ?
O2 C11 C2 114.29(18) . . ?
O2 C12 C13 109.1(2) . . ?
O2 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
O2 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16A C15A C4A 107.0(4) . . ?
C16A C15A H15A 110.3 . . ?
C4A C15A H15A 110.3 . . ?
C16A C15A H15B 110.3 . . ?
C4A C15A H15B 110.3 . . ?
H15A C15A H15B 108.6 . . ?
C15A C16A O3A 106.8(4) . . ?
C15A C16A H16A 110.4 . . ?
O3A C16A H16A 110.4 . . ?
C15A C16A H16B 110.4 . . ?
O3A C16A H16B 110.4 . . ?
H16A C16A H16B 108.6 . . ?
O4 C17 O3B 119.7(2) . . ?
O4 C17 O3A 121.5(2) . . ?
O3B C17 O3A 37.68(16) . . ?
O4 C17 C18 126.6(2) . . ?
O3B C17 C18 110.7(2) . . ?
O3A C17 C18 108.7(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C17 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C17 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 O3B C16B 116.9(3) . . ?
C4B C3B C2 120.3(3) . . ?
C4B C3B H3B 119.9 . . ?
C2 C3B H3B 119.9 . . ?
C3B C4B C10 116.2(3) . . ?
C3B C4B C15B 120.3(3) . . ?
C10 C4B C15B 122.6(3) . . ?
C4B C15B C16B 114.3(3) . . ?
C4B C15B H15C 108.7 . . ?
C16B C15B H15C 108.7 . . ?
C4B C15B H15D 108.7 . . ?
C16B C15B H15D 108.7 . . ?
H15C C15B H15D 107.6 . . ?
O3B C16B C15B 113.0(3) . . ?
O3B C16B H16C 109 . . ?
C15B C16B H16C 109 . . ?
O3B C16B H16D 109 . . ?
C15B C16B H16D 109 . . ?
H16C C16B H16D 107.8 . . ?

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
C9 N1 C2 C3A -16.4(3) . . . . ?
C9 N1 C2 C3B 14.4(3) . . . . ?
C9 N1 C2 C11 -179.74(17) . . . . ?
N1 C2 C3A C4A 15.1(5) . . . . ?
C3B C2 C3A C4A -83.7(7) . . . . ?
C11 C2 C3A C4A 178.5(3) . . . . ?
C2 C3A C4A C10 2.4(6) . . . . ?
C2 C3A C4A C15A 176.7(3) . . . . ?
C10 C5 C6 O5 -178.8(2) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
C19 O5 C6 C5 0.3(3) . . . . ?
C19 O5 C6 C7 179.99(19) . . . . ?
C5 C6 C7 C8 -2.6(4) . . . . ?
O5 C6 C7 C8 177.8(2) . . . . ?
C6 C7 C8 C9 1.7(4) . . . . ?
C2 N1 C9 C8 -179.03(18) . . . . ?
C2 N1 C9 C10 0.7(3) . . . . ?
C7 C8 C9 N1 179.8(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
C6 C5 C10 C4B -162.2(2) . . . . ?
C6 C5 C10 C4A 162.6(3) . . . . ?
N1 C9 C10 C5 179.24(19) . . . . ?
C8 C9 C10 C5 -1.0(3) . . . . ?
N1 C9 C10 C4B -17.5(3) . . . . ?
C8 C9 C10 C4B 162.2(2) . . . . ?
N1 C9 C10 C4A 15.5(3) . . . . ?
C8 C9 C10 C4A -164.8(2) . . . . ?
C3A C4A C10 C5 -179.3(3) . . . . ?
C15A C4A C10 C5 6.4(5) . . . . ?
C3A C4A C10 C9 -16.2(5) . . . . ?
C15A C4A C10 C9 169.4(3) . . . . ?
C3A C4A C10 C4B 84.0(6) . . . . ?
C15A C4A C10 C4B -90.4(6) . . . . ?
C12 O2 C11 O1 -2.9(3) . . . . ?
C12 O2 C11 C2 178.08(17) . . . . ?
N1 C2 C11 O1 172.7(2) . . . . ?
C3A C2 C11 O1 8.6(4) . . . . ?
C3B C2 C11 O1 -20.9(4) . . . . ?
N1 C2 C11 O2 -8.3(3) . . . . ?
C3A C2 C11 O2 -172.3(3) . . . . ?
C3B C2 C11 O2 158.2(2) . . . . ?
C11 O2 C12 C13 171.68(18) . . . . ?
C3A C4A C15A C16A -100.8(5) . . . . ?
C10 C4A C15A C16A 73.2(5) . . . . ?
C4A C15A C16A O3A 178.3(3) . . . . ?
C17 O3A C16A C15A 78.4(4) . . . . ?
C16A O3A C17 O4 5.3(5) . . . . ?
C16A O3A C17 O3B -93.7(4) . . . . ?
C16A O3A C17 C18 166.5(3) . . . . ?
O4 C17 O3B C16B -15.7(4) . . . . ?
O3A C17 O3B C16B 88.6(4) . . . . ?
C18 C17 O3B C16B -177.2(3) . . . . ?
N1 C2 C3B C4B -12.2(5) . . . . ?
C3A C2 C3B C4B 85.6(7) . . . . ?
C11 C2 C3B C4B -178.1(3) . . . . ?
C2 C3B C4B C10 -5.2(5) . . . . ?
C2 C3B C4B C15B -174.3(3) . . . . ?
C5 C10 C4B C3B -178.5(3) . . . . ?
C9 C10 C4B C3B 18.7(4) . . . . ?
C4A C10 C4B C3B -75.9(5) . . . . ?
C5 C10 C4B C15B -9.7(4) . . . . ?
C9 C10 C4B C15B -172.5(3) . . . . ?
C4A C10 C4B C15B 92.9(5) . . . . ?
C3B C4B C15B C16B 94.2(4) . . . . ?
C10 C4B C15B C16B -74.1(4) . . . . ?
C17 O3B C16B C15B -79.9(4) . . . . ?
C4B C15B C16B O3B -178.3(3) . . . . ?