Supplementary Material for Organic & Biomolecular Chemistry
This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_publ_contact_author_name        'Dr.Adam S. Nelson'
_publ_contact_author_address     
;
Department of Chemistry
University of Leeds
Leeds
LS2 9JT
UK
;
_publ_contact_author_email       A.S.Nelson@chemistry.leeds.ac.uk
_publ_contact_author_phone       '+44 (0)113 343 6502'

loop_
_publ_author_name
_publ_author_address
'Adam S. Nelson'
;
Department of Chemistry
University of Leeds
Leeds, LS2 9JT, UK
;
'Alan Berry'
;
School of Biochemistry and Microbiology
University of Leeds
Leeds, LS2 9JT, UK
;
'Gavin J. Williams'
;
School of Biochemistry and Microbiology
University of Leeds
Leeds, LS2 9JT, UK
;
'Thomas Woodhall'
;
Department of Chemistry
University of Leeds
Leeds, LS2 9JT, UK
;

_publ_section_title              
;
Synthesis of screening substrates for the directed
evolution of sialic acid aldolase: Towards tailored enzymes for the
preparation of influenza A sialidase inhibitor analogues
;

data_tw202
_database_code_depnum_ccdc_archive 'CCDC 262317'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H33 N O6'
_chemical_formula_sum            'C19 H33 N O6'
_chemical_formula_weight         371.46
_chemical_absolute_configuration rm

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.73880(10)
_cell_length_b                   9.49090(10)
_cell_length_c                   38.2430(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2082.96(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23058
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
PLEASE NOTE cell_measurement_ fields are
not relevant to area detector data since the
entire data set is used to refine the cell,
which is indexed from all observed
reflections in a 10 degree range.

The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.

;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_probe          x-ray
_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 KappaCCD area-detector diffractometer
;
_diffrn_radiation_detector       'CCD plate'
_diffrn_measurement_method       
;
phi and omega scans to fill the asymmetric unit
;
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16140
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2404
_reflns_number_gt                1800
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_reduction        
;
DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  'local program'

_refine_special_details          
;
The group C7,O7,O8,C9,C10 was disordered over two equally occupied positions.
All H atoms were placed in calculated positions and refined using a riding
model. C-H distances: CH3, 0.98\%A; >CH2, 0.99\%A; =CH2, 0.95\%A;C-H, 1.00\%A.
O-H distance: 0.84\%A. All carbon Uiso(H) values were constrained to be 1.2
times Ueq of the parent atom. The hydoxyl Uiso(H) value was constrained to
be 1.5 times Ueq of the parent atom.
In the absence of significant anomalous scattering effects, the absolute
configuration could not be confirmed from the diffraction data; it was assumed
from the known configuration of the starting material, and Friedel pairs were
merged.

Colin Kilner 14 March 2005

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^)+(0.0612P)^2^+0.1350P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2404
_refine_ls_number_parameters     260
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.2283(5) 0.6648(3) 0.59953(6) 0.0300(6) Uani 1 1 d . . .
C2 C 0.0756(5) 0.7362(3) 0.57193(7) 0.0313(6) Uani 1 1 d . . .
H2 H -0.0186 0.6637 0.5593 0.038 Uiso 1 1 calc R . .
C3 C -0.0853(5) 0.8556(3) 0.58520(7) 0.0290(6) Uani 1 1 d . . .
H3 H -0.2460 0.8394 0.5759 0.035 Uiso 1 1 calc R . .
C4 C -0.1004(5) 0.8809(3) 0.62433(6) 0.0280(6) Uani 1 1 d . . .
H4 H 0.0582 0.9068 0.6330 0.034 Uiso 1 1 calc R . .
C5 C -0.2663(5) 1.0032(3) 0.63219(6) 0.0310(6) Uani 1 1 d . . .
H5A H -0.2016 1.0904 0.6218 0.037 Uiso 1 1 calc R . .
H5B H -0.4178 0.9843 0.6207 0.037 Uiso 1 1 calc R . .
C6 C -0.3074(5) 1.0278(3) 0.67045(6) 0.0312(6) Uani 1 1 d D C .
C7 C -0.1396(7) 1.1207(3) 0.68849(8) 0.0519(9) Uani 1 1 d DU . .
C9A C -0.0880(13) 1.2539(7) 0.74164(18) 0.0440(18) Uani 0.50 1 d PDU A 1
H9A H -0.1905 1.2960 0.7596 0.053 Uiso 0.50 1 calc PR A 1
H9A' H -0.0390 1.3301 0.7256 0.053 Uiso 0.50 1 calc PR A 1
C9B C 0.0539(13) 1.1617(8) 0.7454(2) 0.0511(19) Uani 0.50 1 d PDU B 2
H9B H 0.1034 1.1052 0.7659 0.061 Uiso 0.50 1 calc PR B 2
H9B' H 0.1945 1.1865 0.7318 0.061 Uiso 0.50 1 calc PR B 2
C10A C 0.1221(15) 1.1942(8) 0.7590(2) 0.0527(15) Uani 0.50 1 d PDU A 1
H10A H 0.2061 1.2694 0.7712 0.063 Uiso 0.50 1 calc PR A 1
H10A' H 0.2241 1.1517 0.7414 0.063 Uiso 0.50 1 calc PR A 1
H10A'' H 0.0743 1.1221 0.7759 0.063 Uiso 0.50 1 calc PR A 1
C10B C -0.0612(15) 1.2889(8) 0.7572(2) 0.0527(15) Uani 0.50 1 d PDU B 2
H10B H 0.0463 1.3441 0.7717 0.063 Uiso 0.50 1 calc PR B 2
H10B' H -0.1990 1.2639 0.7710 0.063 Uiso 0.50 1 calc PR B 2
H10B'' H -0.1088 1.3449 0.7369 0.063 Uiso 0.50 1 calc PR B 2
C11 C 0.3217(5) 0.4662(3) 0.63612(6) 0.0322(6) Uani 1 1 d . . .
H11A H 0.4869 0.4875 0.6309 0.039 Uiso 1 1 calc R . .
H11B H 0.3012 0.3628 0.6345 0.039 Uiso 1 1 calc R . .
C12 C 0.2684(5) 0.5125(3) 0.67310(6) 0.0364(7) Uani 1 1 d . . .
H12A H 0.1084 0.4831 0.6794 0.044 Uiso 1 1 calc R . .
H12B H 0.2762 0.6166 0.6746 0.044 Uiso 1 1 calc R . .
C13 C 0.4408(6) 0.4485(4) 0.69871(8) 0.0537(9) Uani 1 1 d . . .
H13A H 0.4034 0.4799 0.7225 0.064 Uiso 1 1 calc R . .
H13B H 0.5990 0.4787 0.6926 0.064 Uiso 1 1 calc R . .
H13C H 0.4312 0.3455 0.6976 0.064 Uiso 1 1 calc R . .
C21 C -0.0451(4) 0.4629(3) 0.60134(6) 0.0301(6) Uani 1 1 d . . .
H21A H -0.1645 0.5349 0.5960 0.036 Uiso 1 1 calc R . .
H21B H -0.0982 0.4100 0.6222 0.036 Uiso 1 1 calc R . .
C22 C -0.0264(5) 0.3616(3) 0.57056(7) 0.0364(7) Uani 1 1 d . . .
H22A H 0.0448 0.4110 0.5504 0.044 Uiso 1 1 calc R . .
H22B H 0.0764 0.2820 0.5770 0.044 Uiso 1 1 calc R . .
C23 C -0.2637(6) 0.3053(3) 0.56008(7) 0.0431(8) Uani 1 1 d . . .
H23A H -0.2461 0.2402 0.5404 0.052 Uiso 1 1 calc R . .
H23B H -0.3645 0.3839 0.5532 0.052 Uiso 1 1 calc R . .
H23C H -0.3337 0.2556 0.5799 0.052 Uiso 1 1 calc R . .
C32 C 0.1318(5) 0.9363(3) 0.53866(6) 0.0309(6) Uani 1 1 d . . .
C33 C -0.0315(6) 0.9197(3) 0.50766(7) 0.0429(8) Uani 1 1 d . . .
H33A H -0.0973 1.0117 0.5015 0.052 Uiso 1 1 calc R . .
H33B H -0.1577 0.8548 0.5138 0.052 Uiso 1 1 calc R . .
H33C H 0.0553 0.8820 0.4877 0.052 Uiso 1 1 calc R . .
C34 C 0.3270(5) 1.0374(3) 0.53204(7) 0.0439(8) Uani 1 1 d . . .
H34A H 0.2629 1.1293 0.5254 0.053 Uiso 1 1 calc R . .
H34B H 0.4255 1.0015 0.5131 0.053 Uiso 1 1 calc R . .
H34C H 0.4205 1.0477 0.5533 0.053 Uiso 1 1 calc R . .
C60 C -0.4843(5) 0.9718(3) 0.68758(7) 0.0386(7) Uani 1 1 d . . .
H60A H -0.5047 0.9912 0.7118 0.046 Uiso 1 1 calc R C .
H60B H -0.5913 0.9122 0.6757 0.046 Uiso 1 1 calc R . .
N1 N 0.1746(4) 0.5338(2) 0.60963(5) 0.0277(5) Uani 1 1 d . . .
O1 O 0.3999(3) 0.7289(2) 0.61073(5) 0.0389(5) Uani 1 1 d . . .
O2 O 0.2307(4) 0.8041(2) 0.54818(5) 0.0407(5) Uani 1 1 d . . .
O3 O 0.0093(3) 0.97961(18) 0.56906(4) 0.0323(5) Uani 1 1 d . . .
O4 O -0.1708(3) 0.75411(19) 0.64121(4) 0.0313(5) Uani 1 1 d . . .
H4' H -0.3048 0.7316 0.6344 0.047 Uiso 1 1 calc R . .
O7A O 0.026(4) 1.178(2) 0.6744(10) 0.042(3) Uani 0.50 1 d PD C 1
O7B O -0.017(4) 1.207(2) 0.6739(10) 0.042(3) Uani 0.50 1 d PD C 2
O8A O -0.2178(8) 1.1509(4) 0.72230(9) 0.0336(10) Uani 0.50 1 d PDU A 1
O8B O -0.1055(9) 1.0788(5) 0.72372(10) 0.0448(11) Uani 0.50 1 d PDU B 2

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
C1 0.0290(16) 0.0306(14) 0.0303(14) -0.0049(11) 0.0038(12) -0.0042(13)
C2 0.0342(15) 0.0296(14) 0.0300(14) -0.0001(12) 0.0010(12) -0.0060(13)
C3 0.0259(15) 0.0308(14) 0.0303(14) 0.0024(11) -0.0003(12) -0.0061(13)
C4 0.0253(14) 0.0285(14) 0.0303(14) 0.0010(11) -0.0006(12) -0.0041(12)
C5 0.0338(15) 0.0315(14) 0.0279(13) 0.0008(11) -0.0024(12) -0.0008(13)
C6 0.0361(16) 0.0271(14) 0.0306(14) 0.0017(11) -0.0002(12) 0.0012(14)
C7 0.067(2) 0.052(2) 0.0364(17) -0.0019(15) 0.0049(17) -0.030(2)
C9A 0.057(4) 0.033(4) 0.041(4) -0.009(3) -0.018(3) -0.004(4)
C9B 0.045(5) 0.056(5) 0.052(5) -0.012(4) 0.000(3) 0.006(4)
C10A 0.061(4) 0.045(3) 0.052(4) 0.000(3) -0.012(3) -0.009(3)
C10B 0.061(4) 0.045(3) 0.052(4) 0.000(3) -0.012(3) -0.009(3)
C11 0.0230(14) 0.0333(15) 0.0403(15) 0.0015(13) -0.0007(12) 0.0018(13)
C12 0.0338(16) 0.0405(16) 0.0349(15) 0.0009(13) -0.0028(13) -0.0003(15)
C13 0.048(2) 0.072(2) 0.0412(17) 0.0037(16) -0.0101(15) 0.000(2)
C21 0.0252(15) 0.0303(14) 0.0347(14) 0.0000(12) 0.0008(11) -0.0057(13)
C22 0.0404(18) 0.0305(15) 0.0384(16) -0.0018(12) 0.0007(14) -0.0034(14)
C23 0.0505(19) 0.0393(17) 0.0397(16) 0.0002(13) -0.0098(15) -0.0091(16)
C32 0.0339(16) 0.0326(15) 0.0261(14) -0.0046(11) 0.0038(12) -0.0019(13)
C33 0.048(2) 0.0470(18) 0.0336(15) 0.0043(13) -0.0018(14) -0.0140(17)
C34 0.0430(19) 0.0532(19) 0.0354(15) 0.0035(15) 0.0027(14) -0.0147(17)
C60 0.0353(16) 0.0477(17) 0.0330(14) -0.0068(14) -0.0018(13) -0.0033(17)
N1 0.0232(12) 0.0288(12) 0.0311(11) 0.0000(10) 0.0003(9) -0.0019(10)
O1 0.0307(11) 0.0397(11) 0.0463(11) 0.0003(9) -0.0033(9) -0.0107(10)
O2 0.0475(13) 0.0380(11) 0.0365(11) 0.0085(9) 0.0165(9) 0.0091(10)
O3 0.0390(11) 0.0288(10) 0.0292(9) -0.0001(8) 0.0071(8) -0.0041(10)
O4 0.0303(11) 0.0336(10) 0.0300(10) 0.0058(8) -0.0006(8) 0.0001(9)
O7A 0.049(6) 0.031(7) 0.0467(15) -0.003(6) 0.004(6) -0.007(5)
O7B 0.049(6) 0.031(7) 0.0467(15) -0.003(6) 0.004(6) -0.007(5)
O8A 0.043(3) 0.027(2) 0.030(2) -0.0035(17) -0.0079(18) 0.004(2)
O8B 0.053(3) 0.046(3) 0.035(2) -0.006(2) -0.004(2) -0.009(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
C1 O1 1.234(3) . ?
C1 N1 1.339(3) . ?
C1 C2 1.529(4) . ?
C2 O2 1.426(3) . ?
C2 C3 1.548(4) . ?
C2 H2 1.0000 . ?
C3 O3 1.435(3) . ?
C3 C4 1.518(3) . ?
C3 H3 1.0000 . ?
C4 O4 1.424(3) . ?
C4 C5 1.531(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.501(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C60 1.320(4) . ?
C6 C7 1.477(4) . ?
C7 O7B 1.215(11) . ?
C7 O7A 1.219(12) . ?
C7 O8A 1.398(5) . ?
C7 O8B 1.418(5) . ?
C9A O8A 1.434(7) . ?
C9A C10A 1.488(9) . ?
C9A H9A 0.9900 . ?
C9A H9A 0.9900 . ?
C9B C10B 1.448(9) . ?
C9B O8B 1.465(8) . ?
C9B H9B 0.9900 . ?
C9B H9B 0.9900 . ?
C10A H10A 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10A 0.9800 . ?
C10B H10B 0.9800 . ?
C10B H10B 0.9800 . ?
C10B H10B 0.9800 . ?
C11 N1 1.466(3) . ?
C11 C12 1.512(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.519(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 N1 1.464(3) . ?
C21 C22 1.523(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.517(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C32 O3 1.419(3) . ?
C32 O2 1.425(3) . ?
C32 C34 1.497(4) . ?
C32 C33 1.519(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C60 H60A 0.9500 . ?
C60 H60B 0.9500 . ?
O4 H4 0.8400 . ?

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
O1 C1 N1 122.7(3) . . ?
O1 C1 C2 118.6(2) . . ?
N1 C1 C2 118.6(2) . . ?
O2 C2 C1 106.4(2) . . ?
O2 C2 C3 104.5(2) . . ?
C1 C2 C3 116.1(2) . . ?
O2 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
O3 C3 C4 108.4(2) . . ?
O3 C3 C2 103.5(2) . . ?
C4 C3 C2 118.2(2) . . ?
O3 C3 H3 108.8 . . ?
C4 C3 H3 108.8 . . ?
C2 C3 H3 108.8 . . ?
O4 C4 C3 109.2(2) . . ?
O4 C4 C5 112.1(2) . . ?
C3 C4 C5 110.4(2) . . ?
O4 C4 H4 108.3 . . ?
C3 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
C6 C5 C4 114.0(2) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.6 . . ?
C60 C6 C7 120.7(3) . . ?
C60 C6 C5 122.8(3) . . ?
C7 C6 C5 116.5(2) . . ?
O7B C7 O7A 17.7(18) . . ?
O7B C7 O8A 118.2(18) . . ?
O7A C7 O8A 124.6(19) . . ?
O7B C7 O8B 123(2) . . ?
O7A C7 O8B 115.9(19) . . ?
O8A C7 O8B 39.1(2) . . ?
O7B C7 C6 124(2) . . ?
O7A C7 C6 125(2) . . ?
O8A C7 C6 110.2(3) . . ?
O8B C7 C6 111.5(3) . . ?
O8A C9A C10A 113.0(6) . . ?
O8A C9A H9A 109.0 . . ?
C10A C9A H9A 109.0 . . ?
O8A C9A H9A 109.0 . . ?
C10A C9A H9A 109.0 . . ?
H9A C9A H9A 107.8 . . ?
C10B C9B O8B 109.8(6) . . ?
C10B C9B H9B 109.7 . . ?
O8B C9B H9B 109.7 . . ?
C10B C9B H9B 109.7 . . ?
O8B C9B H9B 109.7 . . ?
H9B C9B H9B 108.2 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10A 109.5 . . ?
H10A C10A H10A 109.5 . . ?
C9A C10A H10A 109.5 . . ?
H10A C10A H10A 109.5 . . ?
H10A C10A H10A 109.5 . . ?
C9B C10B H10B 109.5 . . ?
C9B C10B H10B 109.5 . . ?
H10B C10B H10B 109.5 . . ?
C9B C10B H10B 109.5 . . ?
H10B C10B H10B 109.5 . . ?
H10B C10B H10B 109.5 . . ?
N1 C11 C12 113.7(2) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 110.8(2) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
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 . . ?
N1 C21 C22 113.4(2) . . ?
N1 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N1 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 111.3(2) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C32 O2 104.07(19) . . ?
O3 C32 C34 108.9(2) . . ?
O2 C32 C34 108.0(2) . . ?
O3 C32 C33 111.3(2) . . ?
O2 C32 C33 110.7(2) . . ?
C34 C32 C33 113.3(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C6 C60 H60A 120.0 . . ?
C6 C60 H60B 120.0 . . ?
H60A C60 H60B 120.0 . . ?
C1 N1 C21 124.2(2) . . ?
C1 N1 C11 118.3(2) . . ?
C21 N1 C11 116.4(2) . . ?
C32 O2 C2 108.2(2) . . ?
C32 O3 C3 107.59(18) . . ?
C4 O4 H4 109.5 . . ?
C7 O8A C9A 116.7(5) . . ?
C7 O8B C9B 118.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.065

data_tw175
_database_code_depnum_ccdc_archive 'CCDC 262318'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H31 N O7'
_chemical_formula_sum            'C17 H31 N O7'
_chemical_formula_weight         361.43
_chemical_absolute_configuration rm

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.7774(4)
_cell_length_b                   8.3066(4)
_cell_length_c                   13.4961(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2110(17)
_cell_angle_gamma                90.00
_cell_volume                     978.23(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17742
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.49

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_special_details           
;
PLEASE NOTE cell_measurement_ fields are
not relevant to area detector data since the
entire data set is used to refine the cell,
which is indexed from all observed
reflections in a 10 degree range.

The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.

;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_probe          x-ray
_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 KappaCCD area-detector diffractometer
;
_diffrn_radiation_detector       'CCD plate'
_diffrn_measurement_method       
;
phi and omega scans to fill the asymmetric unit
;
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10309
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2039
_reflns_number_gt                1860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_reduction        
'DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)'
_computing_structure_solution    
'SIR92 (Altomare, Cascarano, Giacovazzo G., Burla M.C. & Camalli, 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1999)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'local program'

_refine_special_details          
;
All H atoms were placed in calculated positions and refined using a riding
model. C-H distances: CH3, 0.98\%A; >CH2, 0.99\%A; C-H, 1.00\%A.
All carbon Uiso(H) values were constrained to be 1.2
times Ueq of the parent atom.
In the absence of significant anomalous scattering effects, the absolute
configuration could not be confirmed from the diffraction data; it was assumed
from the known configuration of the starting material, and Friedel pairs were
merged.

Colin Kilner 14 March 2005

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^)+(0.0831P)^2^+0.0510P] 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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.076(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^

_refine_ls_number_reflns         2039
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.8323(3) 0.3092(3) 0.27455(18) 0.0348(5) Uani 1 1 d . . .
C2 C 0.8855(3) 0.3635(3) 0.38330(17) 0.0347(5) Uani 1 1 d . . .
C4 C 0.7256(3) 0.5984(3) 0.35772(17) 0.0335(5) Uani 1 1 d . . .
H4 H 0.7368 0.7182 0.3574 0.040 Uiso 1 1 calc R . .
C5 C 0.6814(3) 0.5474(3) 0.25012(18) 0.0335(5) Uani 1 1 d . . .
H5 H 0.7647 0.5878 0.2116 0.040 Uiso 1 1 calc R . .
C10 C 0.8140(3) 0.1284(3) 0.2637(2) 0.0432(6) Uani 1 1 d . . .
H10A H 0.9122 0.0758 0.2845 0.052 Uiso 1 1 calc R . .
H10B H 0.7812 0.1019 0.1938 0.052 Uiso 1 1 calc R . .
H10C H 0.7367 0.0907 0.3055 0.052 Uiso 1 1 calc R . .
C11 C 0.9214(3) 0.3373(4) 0.11244(19) 0.0478(7) Uani 1 1 d . . .
H11A H 1.0042 0.3860 0.0794 0.057 Uiso 1 1 calc R . .
H11B H 0.8228 0.3811 0.0836 0.057 Uiso 1 1 calc R . .
H11C H 0.9222 0.2203 0.1028 0.057 Uiso 1 1 calc R . .
C20 C 1.0534(3) 0.3274(4) 0.41510(19) 0.0420(6) Uani 1 1 d . . .
H20A H 1.0710 0.2112 0.4111 0.050 Uiso 1 1 calc R . .
H20B H 1.0803 0.3638 0.4838 0.050 Uiso 1 1 calc R . .
H20C H 1.1171 0.3837 0.3709 0.050 Uiso 1 1 calc R . .
C21 C 0.8262(3) 0.2811(4) 0.54687(19) 0.0439(6) Uani 1 1 d . . .
H21A H 0.7478 0.2236 0.5793 0.053 Uiso 1 1 calc R . .
H21B H 0.8356 0.3914 0.5726 0.053 Uiso 1 1 calc R . .
H21C H 0.9248 0.2256 0.5608 0.053 Uiso 1 1 calc R . .
C40 C 0.5999(3) 0.5597(3) 0.42460(18) 0.0357(6) Uani 1 1 d . . .
C41 C 0.5392(4) 0.5656(5) 0.5911(2) 0.0556(8) Uani 1 1 d . . .
H41A H 0.5858 0.5938 0.6581 0.067 Uiso 1 1 calc R . .
H41B H 0.5096 0.4518 0.5896 0.067 Uiso 1 1 calc R . .
H41C H 0.4481 0.6323 0.5738 0.067 Uiso 1 1 calc R . .
C50 C 0.5346(3) 0.6326(3) 0.20678(17) 0.0345(5) Uani 1 1 d . . .
C51 C 0.2831(3) 0.6555(3) 0.11858(17) 0.0347(5) Uani 1 1 d . . .
H51A H 0.2234 0.5955 0.0641 0.042 Uiso 1 1 calc R . .
H51B H 0.3251 0.7531 0.0894 0.042 Uiso 1 1 calc R . .
C52 C 0.1770(3) 0.7057(4) 0.19477(18) 0.0405(6) Uani 1 1 d . . .
H52A H 0.2329 0.7784 0.2442 0.049 Uiso 1 1 calc R . .
H52B H 0.1463 0.6090 0.2306 0.049 Uiso 1 1 calc R . .
C53 C 0.0332(3) 0.7912(4) 0.1468(2) 0.0485(7) Uani 1 1 d . . .
H53A H -0.0317 0.8211 0.1986 0.058 Uiso 1 1 calc R . .
H53B H -0.0236 0.7190 0.0987 0.058 Uiso 1 1 calc R . .
H53C H 0.0629 0.8884 0.1125 0.058 Uiso 1 1 calc R . .
C54 C 0.3771(3) 0.3830(3) 0.16692(18) 0.0348(5) Uani 1 1 d . . .
H54A H 0.2686 0.3691 0.1790 0.042 Uiso 1 1 calc R . .
H54B H 0.4417 0.3357 0.2243 0.042 Uiso 1 1 calc R . .
C55 C 0.4049(3) 0.2918(3) 0.07300(19) 0.0439(6) Uani 1 1 d . . .
H55A H 0.3465 0.3441 0.0149 0.053 Uiso 1 1 calc R . .
H55B H 0.5151 0.2981 0.0637 0.053 Uiso 1 1 calc R . .
C56 C 0.3579(4) 0.1163(4) 0.0764(3) 0.0572(8) Uani 1 1 d . . .
H56A H 0.3773 0.0633 0.0141 0.069 Uiso 1 1 calc R . .
H56B H 0.2486 0.1092 0.0846 0.069 Uiso 1 1 calc R . .
H56C H 0.4176 0.0630 0.1326 0.069 Uiso 1 1 calc R . .
N50 N 0.4105(2) 0.5545(2) 0.16177(15) 0.0337(5) Uani 1 1 d . . .
O3 O 0.87165(17) 0.5342(2) 0.39280(13) 0.0352(4) Uani 1 1 d . . .
O6 O 0.68452(17) 0.3764(2) 0.24269(12) 0.0335(4) Uani 1 1 d . . .
O11 O 0.94358(18) 0.3730(2) 0.21682(12) 0.0387(4) Uani 1 1 d . . .
O21 O 0.78300(18) 0.2852(2) 0.44088(12) 0.0369(4) Uani 1 1 d . . .
O40 O 0.4735(2) 0.5146(3) 0.39514(14) 0.0454(5) Uani 1 1 d . . .
O41 O 0.64885(19) 0.5936(2) 0.51977(13) 0.0431(5) Uani 1 1 d . . .
O50 O 0.5419(2) 0.7799(2) 0.21085(14) 0.0453(5) 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
C1 0.0267(11) 0.0398(14) 0.0381(12) -0.0010(10) 0.0049(9) 0.0014(9)
C2 0.0292(11) 0.0393(14) 0.0358(12) 0.0013(10) 0.0045(9) -0.0007(10)
C4 0.0278(11) 0.0352(12) 0.0367(12) -0.0017(10) -0.0005(9) 0.0003(9)
C5 0.0294(11) 0.0345(12) 0.0360(12) -0.0004(10) 0.0010(9) -0.0027(9)
C10 0.0396(14) 0.0403(15) 0.0499(15) -0.0069(12) 0.0051(11) 0.0057(11)
C11 0.0428(14) 0.0645(18) 0.0367(13) -0.0034(13) 0.0069(10) 0.0002(13)
C20 0.0304(12) 0.0513(15) 0.0436(14) 0.0022(11) 0.0013(9) 0.0036(11)
C21 0.0445(14) 0.0512(15) 0.0363(13) 0.0094(12) 0.0068(10) 0.0035(13)
C40 0.0340(13) 0.0376(13) 0.0353(12) -0.0039(10) 0.0025(9) 0.0051(10)
C41 0.0498(16) 0.080(2) 0.0388(14) -0.0045(14) 0.0129(12) 0.0118(15)
C50 0.0339(12) 0.0350(14) 0.0342(12) 0.0006(10) 0.0013(9) 0.0010(10)
C51 0.0316(11) 0.0386(12) 0.0329(11) 0.0005(10) -0.0015(9) 0.0005(10)
C52 0.0414(13) 0.0431(14) 0.0374(13) -0.0004(12) 0.0063(10) 0.0018(12)
C53 0.0418(14) 0.0468(15) 0.0585(16) 0.0002(14) 0.0134(12) 0.0067(13)
C54 0.0293(11) 0.0360(13) 0.0388(13) 0.0022(10) 0.0022(9) -0.0001(10)
C55 0.0454(14) 0.0421(15) 0.0440(14) -0.0045(12) 0.0034(11) -0.0034(12)
C56 0.0638(19) 0.0401(16) 0.067(2) -0.0118(14) 0.0039(15) -0.0030(14)
N50 0.0315(10) 0.0322(11) 0.0363(10) 0.0021(8) -0.0011(8) 0.0015(8)
O3 0.0281(8) 0.0378(9) 0.0388(9) -0.0019(7) -0.0006(6) 0.0001(7)
O6 0.0267(8) 0.0355(9) 0.0376(9) -0.0026(7) 0.0008(6) 0.0003(7)
O11 0.0299(8) 0.0515(11) 0.0354(9) -0.0024(8) 0.0071(6) -0.0021(8)
O21 0.0320(8) 0.0428(10) 0.0364(8) 0.0046(8) 0.0053(6) -0.0011(7)
O40 0.0303(9) 0.0624(13) 0.0432(10) -0.0054(9) 0.0026(7) -0.0008(9)
O41 0.0389(9) 0.0546(12) 0.0360(9) -0.0086(8) 0.0044(7) 0.0048(8)
O50 0.0463(10) 0.0323(10) 0.0547(11) 0.0024(9) -0.0066(8) -0.0009(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
C1 O11 1.416(3) . ?
C1 O6 1.435(3) . ?
C1 C10 1.515(4) . ?
C1 C2 1.558(3) . ?
C2 O21 1.410(3) . ?
C2 O3 1.430(3) . ?
C2 C20 1.519(3) . ?
C4 O3 1.422(3) . ?
C4 C5 1.522(3) . ?
C4 C40 1.533(3) . ?
C4 H4 1.0000 . ?
C5 O6 1.424(3) . ?
C5 C50 1.530(3) . ?
C5 H5 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O11 1.432(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O21 1.440(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C40 O40 1.198(3) . ?
C40 O41 1.339(3) . ?
C41 O41 1.452(3) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C50 O50 1.226(3) . ?
C50 N50 1.354(3) . ?
C51 N50 1.467(3) . ?
C51 C52 1.519(3) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.529(4) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 N50 1.458(3) . ?
C54 C55 1.519(4) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 C56 1.517(4) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 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
O11 C1 O6 110.15(19) . . ?
O11 C1 C10 112.9(2) . . ?
O6 C1 C10 105.9(2) . . ?
O11 C1 C2 104.79(18) . . ?
O6 C1 C2 109.79(18) . . ?
C10 C1 C2 113.4(2) . . ?
O21 C2 O3 110.02(19) . . ?
O21 C2 C20 114.2(2) . . ?
O3 C2 C20 105.1(2) . . ?
O21 C2 C1 103.95(18) . . ?
O3 C2 C1 110.61(19) . . ?
C20 C2 C1 113.04(19) . . ?
O3 C4 C5 109.89(19) . . ?
O3 C4 C40 113.92(19) . . ?
C5 C4 C40 112.23(19) . . ?
O3 C4 H4 106.8 . . ?
C5 C4 H4 106.8 . . ?
C40 C4 H4 106.8 . . ?
O6 C5 C4 109.9(2) . . ?
O6 C5 C50 117.14(19) . . ?
C4 C5 C50 110.64(19) . . ?
O6 C5 H5 106.1 . . ?
C4 C5 H5 106.1 . . ?
C50 C5 H5 106.1 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O11 C11 H11A 109.5 . . ?
O11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O11 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O21 C21 H21A 109.5 . . ?
O21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O21 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O40 C40 O41 125.0(2) . . ?
O40 C40 C4 124.7(2) . . ?
O41 C40 C4 110.1(2) . . ?
O41 C41 H41A 109.5 . . ?
O41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O41 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O50 C50 N50 122.2(2) . . ?
O50 C50 C5 114.0(2) . . ?
N50 C50 C5 123.6(2) . . ?
N50 C51 C52 112.64(19) . . ?
N50 C51 H51A 109.1 . . ?
C52 C51 H51A 109.1 . . ?
N50 C51 H51B 109.1 . . ?
C52 C51 H51B 109.1 . . ?
H51A C51 H51B 107.8 . . ?
C51 C52 C53 112.3(2) . . ?
C51 C52 H52A 109.1 . . ?
C53 C52 H52A 109.1 . . ?
C51 C52 H52B 109.1 . . ?
C53 C52 H52B 109.1 . . ?
H52A C52 H52B 107.9 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
N50 C54 C55 113.3(2) . . ?
N50 C54 H54A 108.9 . . ?
C55 C54 H54A 108.9 . . ?
N50 C54 H54B 108.9 . . ?
C55 C54 H54B 108.9 . . ?
H54A C54 H54B 107.7 . . ?
C56 C55 C54 112.7(2) . . ?
C56 C55 H55A 109.1 . . ?
C54 C55 H55A 109.1 . . ?
C56 C55 H55B 109.1 . . ?
C54 C55 H55B 109.1 . . ?
H55A C55 H55B 107.8 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C50 N50 C54 127.1(2) . . ?
C50 N50 C51 116.5(2) . . ?
C54 N50 C51 115.41(19) . . ?
C4 O3 C2 115.14(18) . . ?
C5 O6 C1 112.97(18) . . ?
C1 O11 C11 115.81(19) . . ?
C2 O21 C21 116.29(19) . . ?
C40 O41 C41 115.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.050