# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Prof Gautam Desiraju'
_publ_contact_author_email       'GAUTAM DESIRAJU@YAHOO.COM'

_publ_section_title              
;
Co-crystal formation and the determination of absolute
configuration
;
_publ_contact_author             
;
Prof. Gautam R. Desiraju
School of Chemistry
Univerisity of Hyderabad
Hyderabad 500 046
India
;
_publ_contact_author_fax         '91 40 23010567'
_publ_contact_author_phone       '91 40 23134828'
loop_
_publ_author_name
'Gautam Desiraju'
'Prashant M Bhatt'

# Attachment 'Desiraju_revised_21june.cif'

data_cc1
_database_code_depnum_ccdc_archive 'CCDC 687157'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3Β-hydroxypregn-5-en-20-one+4iodophenol cocrystal
;
_chemical_name_common            
'3cbeta-hydroxypregn-5-en-20-one+4iodophenol cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '(C21 H32 O2) (C6 H5 I O)'
_chemical_formula_sum            'C27 H37 I O3'
_chemical_formula_weight         536.47

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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'

_cell_length_a                   6.1375(6)
_cell_length_b                   15.5472(15)
_cell_length_c                   25.751(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2457.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5427
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      25.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    1.329
_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      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25526
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         26.02
_reflns_number_total             4847
_reflns_number_gt                4710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0296P)²+0.2305P] where P=(Fo²+2Fc²)/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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(13)
_refine_ls_number_reflns         4847
_refine_ls_number_parameters     311
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0537
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.4251(4) 0.82126(13) 1.20744(7) 0.0253(4) Uani 1 1 d D . .
O2 O 1.0149(4) 1.05337(14) 0.78027(8) 0.0351(5) Uani 1 1 d . . .
O3 O 0.3850(4) 0.29508(14) 0.72477(7) 0.0338(5) Uani 1 1 d D . .
I1 I 0.71815(3) 0.287186(10) 0.953185(6) 0.02407(6) Uani 1 1 d . . .
C1 C 0.4232(4) 0.94843(18) 1.08222(10) 0.0188(6) Uani 1 1 d . . .
H1A H 0.3624 1.0055 1.0732 0.023 Uiso 1 1 calc R . .
H1B H 0.3454 0.9050 1.0611 0.023 Uiso 1 1 calc R . .
C2 C 0.3754(5) 0.93079(16) 1.13945(10) 0.0207(6) Uani 1 1 d . . .
H2A H 0.4359 0.9777 1.1611 0.025 Uiso 1 1 calc R . .
H2B H 0.2160 0.9286 1.1451 0.025 Uiso 1 1 calc R . .
C3 C 0.4772(5) 0.84571(17) 1.15519(10) 0.0196(6) Uani 1 1 d D . .
C4 C 0.7224(5) 0.84939(15) 1.14693(9) 0.0204(5) Uani 1 1 d . . .
H4A H 0.7856 0.8949 1.1692 0.024 Uiso 1 1 calc R . .
H4B H 0.7881 0.7938 1.1572 0.024 Uiso 1 1 calc R . .
C5 C 0.7761(4) 0.86802(15) 1.09067(9) 0.0163(5) Uani 1 1 d . . .
C6 C 0.9115(4) 0.81716(16) 1.06445(10) 0.0180(5) Uani 1 1 d . . .
H6 H 0.9739 0.7701 1.0827 0.022 Uiso 1 1 calc R . .
C7 C 0.9736(4) 0.82765(15) 1.00901(10) 0.0175(5) Uani 1 1 d . . .
H7A H 0.9028 0.7818 0.9883 0.021 Uiso 1 1 calc R . .
H7B H 1.1332 0.8204 1.0057 0.021 Uiso 1 1 calc R . .
C8 C 0.9091(4) 0.91521(16) 0.98665(10) 0.0146(5) Uani 1 1 d . . .
C9 C 0.6837(4) 0.94311(15) 1.00639(9) 0.0146(5) Uani 1 1 d . . .
C10 C 0.6675(4) 0.94714(15) 1.06667(9) 0.0155(5) Uani 1 1 d . . .
C11 C 0.6106(4) 1.02695(16) 0.97912(10) 0.0179(5) Uani 1 1 d . . .
H11A H 0.4594 1.0403 0.9898 0.022 Uiso 1 1 calc R . .
H11B H 0.7048 1.0747 0.9911 0.022 Uiso 1 1 calc R . .
C12 C 0.6198(4) 1.02259(17) 0.91946(10) 0.0176(5) Uani 1 1 d . . .
H12A H 0.5086 0.9814 0.9069 0.021 Uiso 1 1 calc R . .
H12B H 0.5845 1.0799 0.9049 0.021 Uiso 1 1 calc R . .
C13 C 0.8431(4) 0.99468(16) 0.90002(9) 0.0160(5) Uani 1 1 d . . .
C14 C 0.9018(4) 0.90981(16) 0.92775(10) 0.0148(5) Uani 1 1 d . . .
C15 C 1.1012(4) 0.87639(16) 0.89888(10) 0.0185(5) Uani 1 1 d . . .
H15A H 1.1126 0.8131 0.9019 0.022 Uiso 1 1 calc R . .
H15B H 1.2363 0.9028 0.9125 0.022 Uiso 1 1 calc R . .
C16 C 1.0606(5) 0.90353(17) 0.84228(10) 0.0218(6) Uani 1 1 d . . .
H16A H 1.0371 0.8523 0.8201 0.026 Uiso 1 1 calc R . .
H16B H 1.1869 0.9360 0.8286 0.026 Uiso 1 1 calc R . .
C17 C 0.8553(5) 0.96061(17) 0.84288(10) 0.0198(6) Uani 1 1 d . . .
C18 C 1.0128(4) 1.06545(16) 0.90775(10) 0.0195(6) Uani 1 1 d . . .
H18A H 0.9661 1.1176 0.8894 0.029 Uiso 1 1 calc R . .
H18B H 1.1533 1.0463 0.8939 0.029 Uiso 1 1 calc R . .
H18C H 1.0277 1.0779 0.9449 0.029 Uiso 1 1 calc R . .
C19 C 0.7800(5) 1.02846(15) 1.08857(9) 0.0198(5) Uani 1 1 d . . .
H19A H 0.7810 1.0259 1.1266 0.030 Uiso 1 1 calc R . .
H19B H 0.7001 1.0797 1.0773 0.030 Uiso 1 1 calc R . .
H19C H 0.9301 1.0313 1.0757 0.030 Uiso 1 1 calc R . .
C20 C 0.8498(5) 1.02922(18) 0.80143(10) 0.0248(7) Uani 1 1 d . . .
C21 C 0.6319(6) 1.0651(2) 0.78722(13) 0.0440(9) Uani 1 1 d . . .
H21A H 0.6513 1.1196 0.7687 0.066 Uiso 1 1 calc R . .
H21B H 0.5465 1.0749 0.8188 0.066 Uiso 1 1 calc R . .
H21C H 0.5551 1.0242 0.7648 0.066 Uiso 1 1 calc R . .
C22 C 0.4477(5) 0.29441(18) 0.77554(10) 0.0239(6) Uani 1 1 d D . .
C23 C 0.6466(5) 0.33121(19) 0.78807(11) 0.0305(7) Uani 1 1 d . . .
H23 H 0.7317 0.3576 0.7617 0.037 Uiso 1 1 calc R . .
C24 C 0.7223(5) 0.32979(17) 0.83880(10) 0.0246(6) Uani 1 1 d . . .
H24 H 0.8591 0.3548 0.8472 0.030 Uiso 1 1 calc R . .
C25 C 0.5972(4) 0.29165(17) 0.87713(9) 0.0189(5) Uani 1 1 d . . .
C26 C 0.3963(5) 0.25634(17) 0.86525(11) 0.0232(6) Uani 1 1 d . . .
H26 H 0.3098 0.2312 0.8918 0.028 Uiso 1 1 calc R . .
C27 C 0.3214(4) 0.25783(16) 0.81429(10) 0.0219(6) Uani 1 1 d . . .
H27 H 0.1834 0.2337 0.8060 0.026 Uiso 1 1 calc R . .
H1O H 0.455(6) 0.8598(17) 1.2262(9) 0.047(11) Uiso 1 1 d D . .
H3O H 0.289(4) 0.2602(16) 0.7206(10) 0.026(8) Uiso 1 1 d D . .
H3 H 0.407(4) 0.8033(15) 1.1345(9) 0.011(6) Uiso 1 1 d . . .
H8 H 1.013(4) 0.9545(16) 0.9965(9) 0.010(6) Uiso 1 1 d . . .
H9 H 0.588(4) 0.8994(15) 0.9953(9) 0.006(6) Uiso 1 1 d . . .
H14 H 0.781(4) 0.8707(15) 0.9187(9) 0.009(6) Uiso 1 1 d . . .
H17 H 0.737(5) 0.9297(16) 0.8379(10) 0.017(7) Uiso 1 1 d . . .


_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 C3 1.434(3) . ?
O1 H1O 0.791(18) . ?
O2 C20 1.210(4) . ?
O3 C22 1.363(3) . ?
O3 H3O 0.806(17) . ?
I1 C25 2.096(2) . ?
C1 C2 1.528(3) . ?
C1 C10 1.552(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.518(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.521(4) . ?
C3 H3 0.95(2) . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.331(4) . ?
C5 C10 1.530(3) . ?
C6 C7 1.487(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.520(3) . ?
C8 C9 1.536(4) . ?
C8 H8 0.92(3) . ?
C9 C11 1.547(3) . ?
C9 C10 1.557(3) . ?
C9 H9 0.94(3) . ?
C10 C19 1.547(3) . ?
C11 C12 1.539(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.528(4) . ?
C13 C14 1.543(3) . ?
C13 C17 1.566(3) . ?
C14 C15 1.523(3) . ?
C14 H14 0.99(3) . ?
C15 C16 1.538(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.541(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.509(4) . ?
C17 H17 0.88(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.494(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.386(4) . ?
C22 C23 1.386(4) . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(4) . ?
C26 C27 1.391(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
C3 O1 H1O 109(2) . . ?
C22 O3 H3O 109.2(19) . . ?
C2 C1 C10 115.6(2) . . ?
C2 C1 H1A 108.4 . . ?
C10 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
C10 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C1 109.6(2) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 C2 112.9(2) . . ?
O1 C3 C4 111.2(2) . . ?
C2 C3 C4 109.7(2) . . ?
O1 C3 H3 103.9(15) . . ?
C2 C3 H3 105.7(14) . . ?
C4 C3 H3 113.2(15) . . ?
C5 C4 C3 110.9(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 C10 123.0(2) . . ?
C4 C5 C10 116.5(2) . . ?
C5 C6 C7 125.6(2) . . ?
C5 C6 H6 117.2 . . ?
C7 C6 H6 117.2 . . ?
C6 C7 C8 113.1(2) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C7 109.5(2) . . ?
C14 C8 C9 108.6(2) . . ?
C7 C8 C9 111.1(2) . . ?
C14 C8 H8 109.5(16) . . ?
C7 C8 H8 108.0(16) . . ?
C9 C8 H8 110.2(16) . . ?
C8 C9 C11 110.4(2) . . ?
C8 C9 C10 113.5(2) . . ?
C11 C9 C10 113.6(2) . . ?
C8 C9 H9 104.8(15) . . ?
C11 C9 H9 106.9(15) . . ?
C10 C9 H9 106.9(15) . . ?
C5 C10 C19 108.4(2) . . ?
C5 C10 C1 109.1(2) . . ?
C19 C10 C1 109.1(2) . . ?
C5 C10 C9 110.0(2) . . ?
C19 C10 C9 111.6(2) . . ?
C1 C10 C9 108.6(2) . . ?
C12 C11 C9 113.9(2) . . ?
C12 C11 H11A 108.8 . . ?
C9 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C9 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 112.0(2) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C18 111.4(2) . . ?
C12 C13 C14 107.6(2) . . ?
C18 C13 C14 113.4(2) . . ?
C12 C13 C17 116.7(2) . . ?
C18 C13 C17 109.5(2) . . ?
C14 C13 C17 97.73(19) . . ?
C8 C14 C15 118.8(2) . . ?
C8 C14 C13 114.9(2) . . ?
C15 C14 C13 104.7(2) . . ?
C8 C14 H14 107.0(13) . . ?
C15 C14 H14 106.2(14) . . ?
C13 C14 H14 104.0(14) . . ?
C14 C15 C16 103.8(2) . . ?
C14 C15 H15A 111.0 . . ?
C16 C15 H15A 111.0 . . ?
C14 C15 H15B 111.0 . . ?
C16 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 106.3(2) . . ?
C15 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C20 C17 C16 114.7(2) . . ?
C20 C17 C13 115.1(2) . . ?
C16 C17 C13 104.1(2) . . ?
C20 C17 H17 105.3(17) . . ?
C16 C17 H17 111.0(17) . . ?
C13 C17 H17 106.5(17) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C21 121.5(2) . . ?
O2 C20 C17 121.3(3) . . ?
C21 C20 C17 117.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 C27 122.4(3) . . ?
O3 C22 C23 118.0(3) . . ?
C27 C22 C23 119.6(2) . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 I1 118.98(19) . . ?
C26 C25 I1 120.58(19) . . ?
C25 C26 C27 119.8(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 120.1(3) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.062
#===END
data_ccii
_database_code_depnum_ccdc_archive 'CCDC 687158'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3Β-hydroxypregn-5-en-20-one+2,4,6-trichlrophenol cocrystal
;
_chemical_name_common            
'3cbeta-hydroxypregn-5-en-20-one+2,4,6-trichlrophenol cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         '(C21H32O2) (C6H3Cl3O)'
_chemical_formula_sum            'C27 H35 Cl3 O3'
_chemical_formula_weight         513.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   12.211(5)
_cell_length_b                   6.166(2)
_cell_length_c                   17.398(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.607(7)
_cell_angle_gamma                90.00
_cell_volume                     1278.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1075
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      17.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.385
_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      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13213
_diffrn_reflns_av_R_equivalents  0.1371
_diffrn_reflns_av_sigmaI/netI    0.1865
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         26.04
_reflns_number_total             4964
_reflns_number_gt                2120
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.1147P)²+0.0000P] where P=(Fo²+2Fc²)/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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.29(19)
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2232
_refine_ls_R_factor_gt           0.1066
_refine_ls_wR_factor_ref         0.2848
_refine_ls_wR_factor_gt          0.2241
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.0512(5) 1.3640(10) 0.7761(4) 0.0628(17) Uani 1 1 d . . .
O2 O 1.0141(5) 0.7190(12) 0.8732(4) 0.077(2) Uani 1 1 d . . .
O3 O 0.8947(6) 0.2831(11) 0.6471(4) 0.086(2) Uani 1 1 d . . .
Cl1 Cl 0.6597(3) 0.1833(5) 0.59127(18) 0.1001(11) Uani 1 1 d . . .
Cl2 Cl 0.6540(3) 0.8845(6) 0.41036(19) 0.1187(13) Uani 1 1 d . . .
Cl3 Cl 1.0330(3) 0.6466(6) 0.6069(2) 0.1021(11) Uani 1 1 d . . .
C1 C 0.3625(7) 1.3649(12) 0.8537(6) 0.054(2) Uani 1 1 d . . .
H1A H 0.4077 1.4140 0.9036 0.064 Uiso 1 1 calc R . .
H1B H 0.3836 1.4499 0.8123 0.064 Uiso 1 1 calc R . .
C2 C 0.2415(7) 1.4067(15) 0.8529(6) 0.064(3) Uani 1 1 d . . .
H2A H 0.2305 1.5604 0.8605 0.077 Uiso 1 1 calc R . .
H2B H 0.2206 1.3289 0.8960 0.077 Uiso 1 1 calc R . .
C3 C 0.1674(7) 1.3349(14) 0.7758(6) 0.057(3) Uani 1 1 d . . .
C4 C 0.1852(8) 1.0899(14) 0.7676(6) 0.058(3) Uani 1 1 d . . .
H4A H 0.1597 1.0140 0.8093 0.070 Uiso 1 1 calc R . .
H4B H 0.1405 1.0402 0.7176 0.070 Uiso 1 1 calc R . .
C5 C 0.3049(7) 1.0372(13) 0.7718(5) 0.046(2) Uani 1 1 d . . .
C6 C 0.3339(7) 0.9219(15) 0.7148(5) 0.054(2) Uani 1 1 d . . .
H6 H 0.2766 0.8769 0.6734 0.065 Uiso 1 1 calc R . .
C7 C 0.4507(7) 0.8593(15) 0.7120(5) 0.063(3) Uani 1 1 d . . .
H7A H 0.4747 0.9444 0.6717 0.076 Uiso 1 1 calc R . .
H7B H 0.4516 0.7077 0.6971 0.076 Uiso 1 1 calc R . .
C8 C 0.5328(6) 0.8929(12) 0.7898(4) 0.0384(19) Uani 1 1 d . . .
C9 C 0.5100(6) 1.1113(11) 0.8247(4) 0.0341(18) Uani 1 1 d . . .
C10 C 0.3901(7) 1.1200(11) 0.8417(5) 0.047(2) Uani 1 1 d . . .
C11 C 0.6017(6) 1.1626(15) 0.8966(5) 0.058(2) Uani 1 1 d . . .
H11A H 0.5885 1.3070 0.9148 0.070 Uiso 1 1 calc R . .
H11B H 0.5952 1.0616 0.9382 0.070 Uiso 1 1 calc R . .
C12 C 0.7208(7) 1.1525(13) 0.8843(5) 0.051(2) Uani 1 1 d . . .
H12A H 0.7735 1.1749 0.9342 0.061 Uiso 1 1 calc R . .
H12B H 0.7322 1.2665 0.8484 0.061 Uiso 1 1 calc R . .
C13 C 0.7420(6) 0.9295(11) 0.8501(4) 0.0374(19) Uani 1 1 d . . .
C14 C 0.6508(7) 0.9009(12) 0.7751(5) 0.048(2) Uani 1 1 d . . .
C15 C 0.6918(7) 0.7032(17) 0.7357(5) 0.059(3) Uani 1 1 d . . .
H15A H 0.6612 0.7026 0.6794 0.071 Uiso 1 1 calc R . .
H15B H 0.6717 0.5689 0.7582 0.071 Uiso 1 1 calc R . .
C16 C 0.8196(7) 0.736(2) 0.7544(5) 0.074(3) Uani 1 1 d . . .
H16A H 0.8570 0.6023 0.7741 0.088 Uiso 1 1 calc R . .
H16B H 0.8439 0.7772 0.7069 0.088 Uiso 1 1 calc R . .
C17 C 0.8498(7) 0.9118(14) 0.8153(5) 0.046(2) Uani 1 1 d . . .
C18 C 0.7455(8) 0.7519(13) 0.9124(5) 0.054(2) Uani 1 1 d . . .
H18A H 0.6726 0.7374 0.9242 0.081 Uiso 1 1 calc R . .
H18B H 0.7991 0.7906 0.9594 0.081 Uiso 1 1 calc R . .
H18C H 0.7669 0.6167 0.8926 0.081 Uiso 1 1 calc R . .
C19 C 0.3787(7) 0.9956(15) 0.9146(5) 0.054(2) Uani 1 1 d . . .
H19A H 0.3061 1.0226 0.9254 0.081 Uiso 1 1 calc R . .
H19B H 0.4358 1.0422 0.9586 0.081 Uiso 1 1 calc R . .
H19C H 0.3870 0.8433 0.9060 0.081 Uiso 1 1 calc R . .
C20 C 0.9547(7) 0.8789(16) 0.8737(5) 0.055(2) Uani 1 1 d . . .
C21 C 0.9972(8) 1.0513(17) 0.9317(6) 0.077(3) Uani 1 1 d . . .
H21A H 0.9626 1.0375 0.9760 0.116 Uiso 1 1 calc R . .
H21B H 0.9796 1.1907 0.9076 0.116 Uiso 1 1 calc R . .
H21C H 1.0771 1.0375 0.9492 0.116 Uiso 1 1 calc R . .
C22 C 0.8384(10) 0.4199(17) 0.5919(6) 0.067(3) Uani 1 1 d . . .
C23 C 0.7316(9) 0.3963(16) 0.5593(6) 0.061(2) Uani 1 1 d . . .
C24 C 0.6677(9) 0.535(2) 0.5031(6) 0.075(3) Uani 1 1 d . . .
H24 H 0.5914 0.5131 0.4830 0.090 Uiso 1 1 calc R . .
C25 C 0.7267(11) 0.7071(18) 0.4790(6) 0.073(3) Uani 1 1 d . . .
C26 C 0.8363(11) 0.7388(19) 0.5106(6) 0.083(3) Uani 1 1 d . . .
H26 H 0.8731 0.8554 0.4936 0.100 Uiso 1 1 calc R . .
C27 C 0.8957(9) 0.6008(18) 0.5681(6) 0.070(3) Uani 1 1 d . . .


_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 C3 1.432(10) . ?
O2 C20 1.225(11) . ?
O3 C22 1.348(11) . ?
Cl1 C23 1.737(10) . ?
Cl2 C25 1.717(10) . ?
Cl3 C27 1.690(11) . ?
C1 C2 1.497(11) . ?
C1 C10 1.570(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.511(12) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(12) . ?
C4 C5 1.484(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.330(11) . ?
C5 C10 1.507(11) . ?
C6 C7 1.489(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.513(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C14 1.519(11) . ?
C8 C9 1.528(9) . ?
C9 C11 1.519(11) . ?
C9 C10 1.557(11) . ?
C10 C19 1.514(11) . ?
C11 C12 1.517(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.543(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.530(11) . ?
C13 C18 1.536(11) . ?
C13 C17 1.567(10) . ?
C14 C15 1.534(12) . ?
C15 C16 1.537(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.503(13) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C20 1.465(11) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.480(13) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.311(13) . ?
C22 C27 1.425(15) . ?
C23 C24 1.400(14) . ?
C24 C25 1.399(16) . ?
C24 H24 0.9300 . ?
C25 C26 1.345(14) . ?
C26 C27 1.391(14) . ?
C26 H26 0.9300 . ?

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 C1 C10 113.9(7) . . ?
C2 C1 H1A 108.8 . . ?
C10 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
C10 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 110.9(8) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O1 C3 C2 111.3(7) . . ?
O1 C3 C4 106.5(8) . . ?
C2 C3 C4 107.5(8) . . ?
C5 C4 C3 111.6(8) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 120.0(8) . . ?
C6 C5 C10 122.3(8) . . ?
C4 C5 C10 117.7(7) . . ?
C5 C6 C7 125.2(8) . . ?
C5 C6 H6 117.4 . . ?
C7 C6 H6 117.4 . . ?
C6 C7 C8 112.8(7) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C14 108.7(6) . . ?
C7 C8 C9 109.5(6) . . ?
C14 C8 C9 107.5(6) . . ?
C11 C9 C8 110.2(6) . . ?
C11 C9 C10 113.0(6) . . ?
C8 C9 C10 111.5(6) . . ?
C5 C10 C19 109.3(7) . . ?
C5 C10 C9 110.3(6) . . ?
C19 C10 C9 113.8(6) . . ?
C5 C10 C1 107.6(7) . . ?
C19 C10 C1 108.3(7) . . ?
C9 C10 C1 107.2(6) . . ?
C12 C11 C9 115.6(7) . . ?
C12 C11 H11A 108.4 . . ?
C9 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C9 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 109.8(7) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C18 115.0(6) . . ?
C14 C13 C12 106.3(6) . . ?
C18 C13 C12 110.1(6) . . ?
C14 C13 C17 100.3(6) . . ?
C18 C13 C17 109.1(6) . . ?
C12 C13 C17 115.9(6) . . ?
C8 C14 C13 113.7(7) . . ?
C8 C14 C15 117.6(7) . . ?
C13 C14 C15 103.0(6) . . ?
C14 C15 C16 102.4(7) . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C17 C16 C15 109.0(7) . . ?
C17 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C20 C17 C16 115.6(7) . . ?
C20 C17 C13 115.0(7) . . ?
C16 C17 C13 103.0(7) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C17 122.4(8) . . ?
O2 C20 C21 117.6(8) . . ?
C17 C20 C21 119.8(8) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 O3 122.9(11) . . ?
C23 C22 C27 117.8(10) . . ?
O3 C22 C27 119.3(10) . . ?
C22 C23 C24 125.8(10) . . ?
C22 C23 Cl1 118.0(9) . . ?
C24 C23 Cl1 116.1(9) . . ?
C25 C24 C23 115.2(10) . . ?
C25 C24 H24 122.4 . . ?
C23 C24 H24 122.4 . . ?
C26 C25 C24 121.4(10) . . ?
C26 C25 Cl2 120.5(10) . . ?
C24 C25 Cl2 118.1(9) . . ?
C25 C26 C27 121.4(11) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C22 118.4(10) . . ?
C26 C27 Cl3 120.1(10) . . ?
C22 C27 Cl3 121.5(9) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.04
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.096
#===END
data_cciii
_database_code_depnum_ccdc_archive 'CCDC 687159'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Cholesterol-4iodophenol(2:1) cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C27H46O) (C6H5IO)'
_chemical_formula_sum            'C60 H97 I O3'
_chemical_formula_weight         993.28

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3022(4)
_cell_length_b                   10.2952(6)
_cell_length_c                   41.964(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.0320(10)
_cell_angle_gamma                90.00
_cell_volume                     2722.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9534
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    0.630
_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      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28020
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.92
_reflns_number_total             10544
_reflns_number_gt                9819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0541P)²+0.2598P] where P=(Fo²+2Fc²)/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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(13)
_refine_ls_number_reflns         10544
_refine_ls_number_parameters     635
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.264
_refine_ls_shift/su_mean         0.001

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 -0.3563(4) 0.9996(3) 0.27075(6) 0.0386(8) Uani 1 1 d . . .
O2 O 0.9364(4) 0.0516(2) 0.22858(5) 0.0181(5) Uani 1 1 d . . .
O3 O 0.2708(4) 0.9157(3) 0.24534(6) 0.0226(6) Uani 1 1 d . . .
I1 I 0.10919(4) 0.32025(3) 0.246103(5) 0.03572(9) Uani 1 1 d . . .
C1 C -0.3464(5) 0.9222(4) 0.35850(8) 0.0225(8) Uani 1 1 d . . .
H1A H -0.4004 0.8465 0.3705 0.027 Uiso 1 1 calc R . .
H1B H -0.4210 1.0003 0.3663 0.027 Uiso 1 1 calc R . .
C2 C -0.4010(6) 0.9037(4) 0.32320(8) 0.0262(9) Uani 1 1 d . . .
H2A H -0.3363 0.8222 0.3155 0.031 Uiso 1 1 calc R . .
H2B H -0.5568 0.8969 0.3202 0.031 Uiso 1 1 calc R . .
C3 C -0.3193(6) 1.0169(4) 0.30430(8) 0.0274(9) Uani 1 1 d . . .
C4 C -0.0819(6) 1.0312(4) 0.30914(9) 0.0275(9) Uani 1 1 d . . .
H4A H -0.0101 0.9552 0.2997 0.033 Uiso 1 1 calc R . .
H4B H -0.0335 1.1098 0.2978 0.033 Uiso 1 1 calc R . .
C5 C -0.0181(5) 1.0419(4) 0.34392(8) 0.0193(7) Uani 1 1 d . . .
C6 C 0.1107(5) 1.1357(3) 0.35382(8) 0.0191(7) Uani 1 1 d . . .
H6 H 0.1566 1.1970 0.3385 0.023 Uiso 1 1 calc R . .
C7 C 0.1897(5) 1.1522(3) 0.38766(8) 0.0196(7) Uani 1 1 d . . .
H7A H 0.1195 1.2286 0.3971 0.024 Uiso 1 1 calc R . .
H7B H 0.3442 1.1694 0.3876 0.024 Uiso 1 1 calc R . .
C8 C 0.1480(5) 1.0336(3) 0.40830(8) 0.0164(7) Uani 1 1 d . . .
C9 C -0.0771(5) 0.9810(3) 0.40122(8) 0.0167(7) Uani 1 1 d . . .
C10 C -0.1056(5) 0.9373(4) 0.36590(8) 0.0187(7) Uani 1 1 d . . .
C11 C -0.1404(5) 0.8756(3) 0.42512(7) 0.0190(7) Uani 1 1 d . . .
H11A H -0.2926 0.8551 0.4217 0.023 Uiso 1 1 calc R . .
H11B H -0.0586 0.7958 0.4206 0.023 Uiso 1 1 calc R . .
C12 C -0.1041(5) 0.9123(3) 0.46020(8) 0.0170(7) Uani 1 1 d . . .
H12A H -0.1364 0.8365 0.4738 0.020 Uiso 1 1 calc R . .
H12B H -0.2021 0.9835 0.4659 0.020 Uiso 1 1 calc R . .
C13 C 0.1262(5) 0.9560(3) 0.46667(8) 0.0165(7) Uani 1 1 d . . .
C14 C 0.1728(6) 1.0664(3) 0.44326(8) 0.0150(7) Uani 1 1 d . . .
C15 C 0.3849(5) 1.1222(3) 0.45519(8) 0.0171(7) Uani 1 1 d . . .
H15A H 0.3941 1.2163 0.4506 0.021 Uiso 1 1 calc R . .
H15B H 0.5054 1.0773 0.4451 0.021 Uiso 1 1 calc R . .
C16 C 0.3852(5) 1.0973(4) 0.49144(8) 0.0197(7) Uani 1 1 d . . .
H16A H 0.5079 1.0427 0.4978 0.024 Uiso 1 1 calc R . .
H16B H 0.3941 1.1805 0.5032 0.024 Uiso 1 1 calc R . .
C17 C 0.1756(5) 1.0272(3) 0.49863(8) 0.0162(7) Uani 1 1 d . . .
C18 C 0.2760(5) 0.8403(3) 0.46255(8) 0.0161(7) Uani 1 1 d . . .
H18A H 0.2276 0.7674 0.4756 0.024 Uiso 1 1 calc R . .
H18B H 0.4200 0.8652 0.4693 0.024 Uiso 1 1 calc R . .
H18C H 0.2764 0.8143 0.4401 0.024 Uiso 1 1 calc R . .
C19 C 0.0091(5) 0.8090(5) 0.35939(7) 0.0249(8) Uani 1 1 d . . .
H19A H 0.0141 0.7942 0.3363 0.037 Uiso 1 1 calc R . .
H19B H -0.0673 0.7375 0.3695 0.037 Uiso 1 1 calc R . .
H19C H 0.1541 0.8133 0.3682 0.037 Uiso 1 1 calc R . .
C20 C 0.1721(6) 0.9487(3) 0.53005(8) 0.0198(7) Uani 1 1 d . . .
C21 C -0.0586(6) 0.9274(4) 0.54031(9) 0.0339(10) Uani 1 1 d . . .
H21A H -0.0599 0.8734 0.5595 0.051 Uiso 1 1 calc R . .
H21B H -0.1382 0.8837 0.5231 0.051 Uiso 1 1 calc R . .
H21C H -0.1245 1.0115 0.5448 0.051 Uiso 1 1 calc R . .
C22 C 0.2968(6) 1.0171(4) 0.55678(8) 0.0243(8) Uani 1 1 d . . .
H22A H 0.4447 1.0294 0.5498 0.029 Uiso 1 1 calc R . .
H22B H 0.2347 1.1044 0.5599 0.029 Uiso 1 1 calc R . .
C23 C 0.3020(7) 0.9469(4) 0.58875(8) 0.0286(9) Uani 1 1 d . . .
H23A H 0.3450 0.8555 0.5853 0.034 Uiso 1 1 calc R . .
H23B H 0.1572 0.9464 0.5975 0.034 Uiso 1 1 calc R . .
C24 C 0.4539(7) 1.0092(5) 0.61300(9) 0.0359(10) Uani 1 1 d . . .
H24A H 0.5956 1.0150 0.6033 0.043 Uiso 1 1 calc R . .
H24B H 0.4051 1.0991 0.6169 0.043 Uiso 1 1 calc R . .
C25 C 0.4796(8) 0.9421(5) 0.64485(9) 0.0412(12) Uani 1 1 d . . .
C26 C 0.2708(9) 0.9434(6) 0.66345(11) 0.0570(14) Uani 1 1 d . . .
H26A H 0.2229 1.0333 0.6661 0.085 Uiso 1 1 calc R . .
H26B H 0.2946 0.9038 0.6844 0.085 Uiso 1 1 calc R . .
H26C H 0.1622 0.8941 0.6516 0.085 Uiso 1 1 calc R . .
C27 C 0.6499(9) 1.0083(7) 0.66558(12) 0.0683(18) Uani 1 1 d . . .
H27A H 0.7810 1.0164 0.6535 0.102 Uiso 1 1 calc R . .
H27B H 0.6772 0.9561 0.6848 0.102 Uiso 1 1 calc R . .
H27C H 0.6007 1.0949 0.6718 0.102 Uiso 1 1 calc R . .
C28 C 0.8741(5) -0.0412(4) 0.14221(8) 0.0186(7) Uani 1 1 d . . .
H28A H 0.9216 -0.1189 0.1304 0.022 Uiso 1 1 calc R . .
H28B H 0.9487 0.0350 0.1334 0.022 Uiso 1 1 calc R . .
C29 C 0.9393(5) -0.0563(4) 0.17714(8) 0.0200(7) Uani 1 1 d . . .
H29A H 0.8738 -0.1356 0.1860 0.024 Uiso 1 1 calc R . .
H29B H 1.0954 -0.0654 0.1790 0.024 Uiso 1 1 calc R . .
C30 C 0.8684(5) 0.0610(3) 0.19579(8) 0.0184(7) Uani 1 1 d . . .
C31 C 0.6268(5) 0.0763(4) 0.19289(8) 0.0184(7) Uani 1 1 d . . .
H31A H 0.5577 0.0019 0.2034 0.022 Uiso 1 1 calc R . .
H31B H 0.5836 0.1566 0.2040 0.022 Uiso 1 1 calc R . .
C32 C 0.5524(5) 0.0830(3) 0.15864(8) 0.0168(7) Uani 1 1 d . . .
C33 C 0.4204(5) 0.1762(3) 0.14873(8) 0.0176(7) Uani 1 1 d . . .
H33 H 0.3782 0.2385 0.1641 0.021 Uiso 1 1 calc R . .
C34 C 0.3333(5) 0.1912(3) 0.11572(8) 0.0181(7) Uani 1 1 d . . .
H34A H 0.4005 0.2674 0.1056 0.022 Uiso 1 1 calc R . .
H34B H 0.1789 0.2082 0.1167 0.022 Uiso 1 1 calc R . .
C35 C 0.3702(5) 0.0712(4) 0.09498(8) 0.0149(7) Uani 1 1 d . . .
C36 C 0.5945(5) 0.0176(3) 0.10127(8) 0.0149(7) Uani 1 1 d . . .
C37 C 0.6309(5) -0.0235(3) 0.13633(7) 0.0142(7) Uani 1 1 d . . .
C38 C 0.6507(5) -0.0891(3) 0.07735(8) 0.0171(7) Uani 1 1 d . . .
H38A H 0.8025 -0.1116 0.0803 0.020 Uiso 1 1 calc R . .
H38B H 0.5666 -0.1677 0.0822 0.020 Uiso 1 1 calc R . .
C39 C 0.6103(5) -0.0518(3) 0.04242(8) 0.0160(7) Uani 1 1 d . . .
H39A H 0.7082 0.0191 0.0365 0.019 Uiso 1 1 calc R . .
H39B H 0.6404 -0.1275 0.0287 0.019 Uiso 1 1 calc R . .
C40 C 0.3819(5) -0.0076(3) 0.03647(7) 0.0138(6) Uani 1 1 d . . .
C41 C 0.3392(5) 0.1033(3) 0.05992(8) 0.0134(6) Uani 1 1 d . . .
C42 C 0.1244(5) 0.1597(3) 0.04876(8) 0.0173(7) Uani 1 1 d . . .
H42A H 0.1152 0.2535 0.0537 0.021 Uiso 1 1 calc R . .
H42B H 0.0053 0.1139 0.0590 0.021 Uiso 1 1 calc R . .
C43 C 0.1216(5) 0.1364(3) 0.01230(8) 0.0182(7) Uani 1 1 d . . .
H43A H -0.0027 0.0831 0.0059 0.022 Uiso 1 1 calc R . .
H43B H 0.1142 0.2201 0.0007 0.022 Uiso 1 1 calc R . .
C44 C 0.3297(5) 0.0644(3) 0.00469(8) 0.0143(7) Uani 1 1 d . . .
C45 C 0.2293(5) -0.1231(3) 0.04061(8) 0.0161(7) Uani 1 1 d . . .
H45A H 0.2703 -0.1940 0.0264 0.024 Uiso 1 1 calc R . .
H45B H 0.0841 -0.0956 0.0353 0.024 Uiso 1 1 calc R . .
H45C H 0.2366 -0.1534 0.0628 0.024 Uiso 1 1 calc R . .
C46 C 0.5154(5) -0.1516(3) 0.14403(8) 0.0200(9) Uani 1 1 d . . .
H46A H 0.5163 -0.1650 0.1672 0.030 Uiso 1 1 calc R . .
H46B H 0.5881 -0.2241 0.1338 0.030 Uiso 1 1 calc R . .
H46C H 0.3685 -0.1469 0.1361 0.030 Uiso 1 1 calc R . .
C47 C 0.3276(5) -0.0128(3) -0.02675(8) 0.0179(7) Uani 1 1 d . . .
C48 C 0.5552(7) -0.0406(4) -0.03739(9) 0.0324(10) Uani 1 1 d . . .
H48A H 0.5508 -0.0899 -0.0574 0.049 Uiso 1 1 calc R . .
H48B H 0.6299 -0.0913 -0.0209 0.049 Uiso 1 1 calc R . .
H48C H 0.6299 0.0416 -0.0407 0.049 Uiso 1 1 calc R . .
C49 C 0.2066(6) 0.0598(4) -0.05329(8) 0.0219(8) Uani 1 1 d . . .
H49A H 0.0599 0.0755 -0.0462 0.026 Uiso 1 1 calc R . .
H49B H 0.2744 0.1457 -0.0562 0.026 Uiso 1 1 calc R . .
C50 C 0.1958(6) -0.0087(4) -0.08554(8) 0.0243(8) Uani 1 1 d . . .
H50A H 0.3385 -0.0079 -0.0950 0.029 Uiso 1 1 calc R . .
H50B H 0.1546 -0.1005 -0.0823 0.029 Uiso 1 1 calc R . .
C51 C 0.0385(6) 0.0544(4) -0.10867(9) 0.0280(9) Uani 1 1 d . . .
H51A H -0.1006 0.0597 -0.0982 0.034 Uiso 1 1 calc R . .
H51B H 0.0862 0.1445 -0.1126 0.034 Uiso 1 1 calc R . .
C52 C 0.0058(6) -0.0118(4) -0.14056(9) 0.0295(9) Uani 1 1 d . . .
C53 C 0.2075(7) -0.0099(5) -0.16083(10) 0.0411(11) Uani 1 1 d . . .
H53A H 0.2371 0.0794 -0.1675 0.062 Uiso 1 1 calc R . .
H53B H 0.1856 -0.0646 -0.1797 0.062 Uiso 1 1 calc R . .
H53C H 0.3278 -0.0432 -0.1482 0.062 Uiso 1 1 calc R . .
C54 C -0.1734(7) 0.0524(6) -0.15948(11) 0.0515(14) Uani 1 1 d . . .
H54A H -0.3003 0.0568 -0.1464 0.077 Uiso 1 1 calc R . .
H54B H -0.2047 0.0013 -0.1787 0.077 Uiso 1 1 calc R . .
H54C H -0.1308 0.1404 -0.1656 0.077 Uiso 1 1 calc R . .
C55 C 0.2322(6) 0.7858(3) 0.24642(8) 0.0193(8) Uani 1 1 d . . .
C56 C 0.0330(6) 0.7363(4) 0.25265(9) 0.0264(8) Uani 1 1 d . . .
H56 H -0.0816 0.7940 0.2564 0.032 Uiso 1 1 calc R . .
C57 C -0.0006(6) 0.6043(4) 0.25351(9) 0.0297(9) Uani 1 1 d . . .
H57 H -0.1378 0.5708 0.2576 0.036 Uiso 1 1 calc R . .
C58 C 0.1696(6) 0.5197(4) 0.24830(8) 0.0254(8) Uani 1 1 d . . .
C59 C 0.3671(6) 0.5698(4) 0.24240(9) 0.0291(9) Uani 1 1 d . . .
H59 H 0.4827 0.5126 0.2389 0.035 Uiso 1 1 calc R . .
C60 C 0.3991(7) 0.7014(4) 0.24155(10) 0.0277(8) Uani 1 1 d . . .
H60 H 0.5367 0.7348 0.2376 0.033 Uiso 1 1 calc R . .
H3 H -0.383(6) 1.099(4) 0.3116(10) 0.024(10) Uiso 1 1 d . . .
H8 H 0.254(6) 0.966(4) 0.4029(8) 0.018(9) Uiso 1 1 d . . .
H9 H -0.173(6) 1.051(4) 0.4030(9) 0.024(10) Uiso 1 1 d . . .
H14 H 0.079(6) 1.111(4) 0.4456(9) 0.014(10) Uiso 1 1 d . . .
H17 H 0.071(4) 1.094(3) 0.5004(7) 0.000(7) Uiso 1 1 d . . .
H20 H 0.233(6) 0.868(4) 0.5260(8) 0.019(10) Uiso 1 1 d . . .
H30 H 0.934(5) 0.140(3) 0.1879(8) 0.006(8) Uiso 1 1 d . . .
H35 H 0.288(6) 0.024(4) 0.0982(8) 0.008(10) Uiso 1 1 d . . .
H36 H 0.682(5) 0.088(3) 0.0975(7) 0.000(7) Uiso 1 1 d . . .
H41 H 0.441(5) 0.174(3) 0.0552(8) 0.003(8) Uiso 1 1 d . . .
H44 H 0.436(5) 0.125(3) 0.0029(7) 0.001(7) Uiso 1 1 d . . .
H47 H 0.260(5) -0.093(4) -0.0230(8) 0.011(8) Uiso 1 1 d . . .


_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 C3 1.434(4) . ?
O2 C30 1.437(4) . ?
O3 C55 1.361(5) . ?
I1 C58 2.091(4) . ?
C1 C2 1.527(5) . ?
C1 C10 1.552(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.506(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(5) . ?
C3 H3 0.98(4) . ?
C4 C5 1.511(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.324(5) . ?
C5 C10 1.527(5) . ?
C6 C7 1.506(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.522(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.511(5) . ?
C8 C9 1.542(5) . ?
C8 H8 1.00(4) . ?
C9 C11 1.535(5) . ?
C9 C10 1.556(5) . ?
C9 H9 0.94(4) . ?
C10 C19 1.533(6) . ?
C11 C12 1.533(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.539(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.532(4) . ?
C13 C14 1.534(5) . ?
C13 C17 1.555(5) . ?
C14 C15 1.531(5) . ?
C14 H14 0.76(4) . ?
C15 C16 1.542(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.540(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.547(5) . ?
C17 H17 0.96(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.530(5) . ?
C20 C21 1.539(5) . ?
C20 H20 0.93(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.524(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.526(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.511(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C27 1.530(7) . ?
C25 C26 1.542(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.523(5) . ?
C28 C37 1.559(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.511(5) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.533(5) . ?
C30 H30 0.97(3) . ?
C31 C32 1.505(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.332(5) . ?
C32 C37 1.530(4) . ?
C33 C34 1.489(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.532(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C41 1.517(4) . ?
C35 C36 1.535(5) . ?
C35 H35 0.72(4) . ?
C36 C38 1.534(4) . ?
C36 C37 1.544(4) . ?
C36 H36 0.92(3) . ?
C37 C46 1.543(5) . ?
C38 C39 1.532(4) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.525(4) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.535(4) . ?
C40 C45 1.541(4) . ?
C40 C44 1.556(4) . ?
C41 C42 1.538(4) . ?
C41 H41 0.99(3) . ?
C42 C43 1.548(5) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.545(5) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C47 1.540(5) . ?
C44 H44 0.92(3) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 C49 1.533(5) . ?
C47 C48 1.537(5) . ?
C47 H47 0.94(4) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 C50 1.527(5) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.521(5) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.513(5) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C54 1.520(6) . ?
C52 C53 1.542(6) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 C60 1.382(5) . ?
C55 C56 1.384(6) . ?
C56 C57 1.376(6) . ?
C56 H56 0.9500 . ?
C57 C58 1.402(6) . ?
C57 H57 0.9500 . ?
C58 C59 1.374(6) . ?
C59 C60 1.370(6) . ?
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?

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 C1 C10 114.1(3) . . ?
C2 C1 H1A 108.7 . . ?
C10 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C10 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 110.0(3) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O1 C3 C2 111.7(3) . . ?
O1 C3 C4 106.7(3) . . ?
C2 C3 C4 110.6(3) . . ?
O1 C3 H3 111(2) . . ?
C2 C3 H3 111(2) . . ?
C4 C3 H3 106(2) . . ?
C5 C4 C3 112.5(3) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 C10 123.5(3) . . ?
C4 C5 C10 116.1(3) . . ?
C5 C6 C7 124.6(3) . . ?
C5 C6 H6 117.7 . . ?
C7 C6 H6 117.7 . . ?
C6 C7 C8 112.9(3) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C14 C8 C7 111.0(3) . . ?
C14 C8 C9 110.1(3) . . ?
C7 C8 C9 109.9(3) . . ?
C14 C8 H8 109(2) . . ?
C7 C8 H8 108(2) . . ?
C9 C8 H8 109(2) . . ?
C11 C9 C8 111.8(3) . . ?
C11 C9 C10 113.0(3) . . ?
C8 C9 C10 112.0(3) . . ?
C11 C9 H9 108(2) . . ?
C8 C9 H9 108(2) . . ?
C10 C9 H9 104(2) . . ?
C5 C10 C19 108.9(3) . . ?
C5 C10 C1 108.2(3) . . ?
C19 C10 C1 109.9(3) . . ?
C5 C10 C9 109.5(3) . . ?
C19 C10 C9 111.8(3) . . ?
C1 C10 C9 108.4(3) . . ?
C12 C11 C9 114.7(3) . . ?
C12 C11 H11A 108.6 . . ?
C9 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C9 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 111.4(3) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C18 C13 C14 112.2(3) . . ?
C18 C13 C12 109.5(3) . . ?
C14 C13 C12 107.1(3) . . ?
C18 C13 C17 110.5(3) . . ?
C14 C13 C17 99.5(3) . . ?
C12 C13 C17 117.6(3) . . ?
C8 C14 C15 118.4(3) . . ?
C8 C14 C13 116.1(3) . . ?
C15 C14 C13 104.2(3) . . ?
C8 C14 H14 101(3) . . ?
C15 C14 H14 114(3) . . ?
C13 C14 H14 102(3) . . ?
C14 C15 C16 104.2(3) . . ?
C14 C15 H15A 110.9 . . ?
C16 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C16 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 C15 106.6(3) . . ?
C17 C16 H16A 110.4 . . ?
C15 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 C20 115.9(3) . . ?
C16 C17 C13 102.2(3) . . ?
C20 C17 C13 118.9(3) . . ?
C16 C17 H17 105.9(17) . . ?
C20 C17 H17 106.7(18) . . ?
C13 C17 H17 106.2(18) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C21 109.6(3) . . ?
C22 C20 C17 111.7(3) . . ?
C21 C20 C17 109.9(3) . . ?
C22 C20 H20 110(2) . . ?
C21 C20 H20 109(2) . . ?
C17 C20 H20 107(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C20 115.4(3) . . ?
C23 C22 H22A 108.4 . . ?
C20 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C20 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
C22 C23 C24 113.0(4) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 117.0(4) . . ?
C25 C24 H24A 108.1 . . ?
C23 C24 H24A 108.1 . . ?
C25 C24 H24B 108.1 . . ?
C23 C24 H24B 108.1 . . ?
H24A C24 H24B 107.3 . . ?
C24 C25 C27 111.2(4) . . ?
C24 C25 C26 111.4(4) . . ?
C27 C25 C26 107.7(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C37 114.3(3) . . ?
C29 C28 H28A 108.7 . . ?
C37 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C37 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C30 C29 C28 109.9(3) . . ?
C30 C29 H29A 109.7 . . ?
C28 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
C28 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
O2 C30 C29 110.9(3) . . ?
O2 C30 C31 111.2(3) . . ?
C29 C30 C31 110.1(3) . . ?
O2 C30 H30 105(2) . . ?
C29 C30 H30 111.3(19) . . ?
C31 C30 H30 108.2(19) . . ?
C32 C31 C30 111.9(3) . . ?
C32 C31 H31A 109.2 . . ?
C30 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C30 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C33 C32 C31 120.9(3) . . ?
C33 C32 C37 122.2(3) . . ?
C31 C32 C37 116.9(3) . . ?
C32 C33 C34 125.7(3) . . ?
C32 C33 H33 117.2 . . ?
C34 C33 H33 117.2 . . ?
C33 C34 C35 112.8(3) . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34B 109.0 . . ?
C35 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C41 C35 C34 110.9(3) . . ?
C41 C35 C36 110.3(3) . . ?
C34 C35 C36 109.9(3) . . ?
C41 C35 H35 104(3) . . ?
C34 C35 H35 108(3) . . ?
C36 C35 H35 113(3) . . ?
C38 C36 C35 111.5(3) . . ?
C38 C36 C37 113.3(3) . . ?
C35 C36 C37 112.5(3) . . ?
C38 C36 H36 107.7(19) . . ?
C35 C36 H36 103.8(19) . . ?
C37 C36 H36 107.4(19) . . ?
C32 C37 C46 109.0(3) . . ?
C32 C37 C36 110.0(3) . . ?
C46 C37 C36 111.8(3) . . ?
C32 C37 C28 108.3(3) . . ?
C46 C37 C28 109.5(3) . . ?
C36 C37 C28 108.2(3) . . ?
C39 C38 C36 114.2(3) . . ?
C39 C38 H38A 108.7 . . ?
C36 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C36 C38 H38B 108.7 . . ?
H38A C38 H38B 107.6 . . ?
C40 C39 C38 111.8(3) . . ?
C40 C39 H39A 109.3 . . ?
C38 C39 H39A 109.3 . . ?
C40 C39 H39B 109.3 . . ?
C38 C39 H39B 109.3 . . ?
H39A C39 H39B 107.9 . . ?
C39 C40 C41 107.0(3) . . ?
C39 C40 C45 109.9(3) . . ?
C41 C40 C45 112.6(3) . . ?
C39 C40 C44 117.8(3) . . ?
C41 C40 C44 99.1(3) . . ?
C45 C40 C44 110.0(3) . . ?
C35 C41 C40 116.0(3) . . ?
C35 C41 C42 118.3(3) . . ?
C40 C41 C42 104.4(3) . . ?
C35 C41 H41 106.3(19) . . ?
C40 C41 H41 107.2(18) . . ?
C42 C41 H41 103.4(18) . . ?
C41 C42 C43 103.7(3) . . ?
C41 C42 H42A 111.0 . . ?
C43 C42 H42A 111.0 . . ?
C41 C42 H42B 111.0 . . ?
C43 C42 H42B 111.0 . . ?
H42A C42 H42B 109.0 . . ?
C44 C43 C42 106.5(3) . . ?
C44 C43 H43A 110.4 . . ?
C42 C43 H43A 110.4 . . ?
C44 C43 H43B 110.4 . . ?
C42 C43 H43B 110.4 . . ?
H43A C43 H43B 108.6 . . ?
C47 C44 C43 115.5(3) . . ?
C47 C44 C40 119.1(3) . . ?
C43 C44 C40 102.6(3) . . ?
C47 C44 H44 106.1(19) . . ?
C43 C44 H44 108.2(18) . . ?
C40 C44 H44 104.5(19) . . ?
C40 C45 H45A 109.5 . . ?
C40 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C40 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C37 C46 H46A 109.5 . . ?
C37 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C37 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C49 C47 C48 109.5(3) . . ?
C49 C47 C44 111.5(3) . . ?
C48 C47 C44 110.6(3) . . ?
C49 C47 H47 109(2) . . ?
C48 C47 H47 108(2) . . ?
C44 C47 H47 108(2) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 C47 115.6(3) . . ?
C50 C49 H49A 108.4 . . ?
C47 C49 H49A 108.4 . . ?
C50 C49 H49B 108.4 . . ?
C47 C49 H49B 108.4 . . ?
H49A C49 H49B 107.4 . . ?
C51 C50 C49 112.7(3) . . ?
C51 C50 H50A 109.0 . . ?
C49 C50 H50A 109.0 . . ?
C51 C50 H50B 109.0 . . ?
C49 C50 H50B 109.0 . . ?
H50A C50 H50B 107.8 . . ?
C52 C51 C50 116.7(3) . . ?
C52 C51 H51A 108.1 . . ?
C50 C51 H51A 108.1 . . ?
C52 C51 H51B 108.1 . . ?
C50 C51 H51B 108.1 . . ?
H51A C51 H51B 107.3 . . ?
C51 C52 C54 110.7(4) . . ?
C51 C52 C53 112.4(3) . . ?
C54 C52 C53 108.6(3) . . ?
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 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O3 C55 C60 118.4(3) . . ?
O3 C55 C56 122.1(3) . . ?
C60 C55 C56 119.5(3) . . ?
C57 C56 C55 120.6(4) . . ?
C57 C56 H56 119.7 . . ?
C55 C56 H56 119.7 . . ?
C56 C57 C58 119.4(4) . . ?
C56 C57 H57 120.3 . . ?
C58 C57 H57 120.3 . . ?
C59 C58 C57 119.6(4) . . ?
C59 C58 I1 121.7(3) . . ?
C57 C58 I1 118.5(3) . . ?
C60 C59 C58 120.6(4) . . ?
C60 C59 H59 119.7 . . ?
C58 C59 H59 119.7 . . ?
C59 C60 C55 120.3(4) . . ?
C59 C60 H60 119.8 . . ?
C55 C60 H60 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.92
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.088
_chemical_name_common            'Cholesterol-4iodophenol(2:1) cocrystal'

#===END
data_cciv
_database_code_depnum_ccdc_archive 'CCDC 687160'
_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
'Lamivudine + Zidovudine hydrate'
;
_chemical_name_common            "'Lamivudine + Zidovudine hydrate'"
_chemical_melting_point          100
_chemical_formula_moiety         'C10 H13 N5 O4, C8 H11 N3 O3 S, H2 O'
_chemical_formula_sum            'C18 H26 N8 O8 S'
_chemical_formula_weight         514.53

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   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.6899(10)
_cell_length_b                   7.2501(9)
_cell_length_c                   18.504(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.506(2)
_cell_angle_gamma                90.00
_cell_volume                     1164.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4965
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.201
_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      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11952
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.10
_diffrn_reflns_theta_max         26.06
_reflns_number_total             4557
_reflns_number_gt                4206
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0649P)²+0.0862P] where P=(Fo²+2Fc²)/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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_number_reflns         4557
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.034
_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
S1 S 0.70005(6) 0.59785(9) 0.45289(3) 0.04971(16) Uani 1 1 d . . .
N4 N 0.97612(19) 1.0053(3) 0.09772(8) 0.0407(4) Uani 1 1 d . . .
O1 O 0.92366(16) 1.0969(2) 0.21593(7) 0.0408(3) Uani 1 1 d . . .
N5 N 1.0365(2) 0.9829(3) -0.02242(9) 0.0465(5) Uani 1 1 d . . .
O4 O 1.2790(2) 0.9610(4) -0.05779(9) 0.0664(6) Uani 1 1 d . . .
O7 O 0.25525(17) 0.3468(3) 0.34142(9) 0.0622(5) Uani 1 1 d . . .
C16 C 0.3605(2) 0.3707(3) 0.29945(11) 0.0411(5) Uani 1 1 d . . .
N7 N 0.33507(19) 0.4040(3) 0.22815(10) 0.0483(5) Uani 1 1 d . . .
O5 O 0.68386(16) 0.2481(2) 0.41854(7) 0.0397(3) Uani 1 1 d . . .
O3 O 0.78702(18) 0.9924(4) 0.00890(8) 0.0625(5) Uani 1 1 d . . .
C2 C 0.8580(2) 1.0110(3) 0.15288(10) 0.0385(4) Uani 1 1 d . . .
O6 O 0.96311(18) 0.4337(3) 0.36954(9) 0.0510(4) Uani 1 1 d . . .
N6 N 0.51126(18) 0.3583(2) 0.32744(8) 0.0330(3) Uani 1 1 d . . .
C12 C 0.5345(2) 0.3185(3) 0.40588(10) 0.0362(4) Uani 1 1 d . . .
C19 C 0.6319(2) 0.3815(3) 0.28356(10) 0.0329(4) Uani 1 1 d . . .
H19 H 0.7322 0.3736 0.3030 0.040 Uiso 1 1 calc R . .
C17 C 0.4534(2) 0.4264(3) 0.18542(11) 0.0392(5) Uani 1 1 d . . .
N1 N 0.6135(2) 0.9335(4) 0.25719(12) 0.0610(6) Uani 1 1 d . . .
N8 N 0.4252(3) 0.4592(4) 0.11591(11) 0.0563(6) Uani 1 1 d . . .
O2 O 1.0205(3) 0.8258(3) 0.37830(10) 0.0654(5) Uani 1 1 d . . .
N2 N 0.5350(2) 0.8894(3) 0.30447(13) 0.0583(6) Uani 1 1 d . . .
C8 C 1.1923(3) 0.9736(4) -0.00801(11) 0.0445(5) Uani 1 1 d . . .
C10 C 1.1306(2) 0.9961(4) 0.11594(11) 0.0465(5) Uani 1 1 d . . .
H10 H 1.1606 1.0004 0.1648 0.056 Uiso 1 1 calc R . .
C18 C 0.6079(2) 0.4154(3) 0.21351(11) 0.0359(4) Uani 1 1 d . . .
H18 H 0.6901 0.4314 0.1836 0.043 Uiso 1 1 calc R . .
C7 C 0.9229(3) 0.9945(4) 0.02674(11) 0.0436(5) Uani 1 1 d . . .
C13 C 0.5135(2) 0.4887(4) 0.45148(12) 0.0454(5) Uani 1 1 d . . .
H13A H 0.4851 0.4560 0.5000 0.054 Uiso 1 1 calc R . .
H13B H 0.4350 0.5689 0.4298 0.054 Uiso 1 1 calc R . .
C9 C 1.2412(2) 0.9813(4) 0.06787(11) 0.0459(5) Uani 1 1 d . . .
C3 C 0.8051(3) 0.8217(3) 0.17587(11) 0.0447(5) Uani 1 1 d . . .
H3A H 0.8854 0.7304 0.1707 0.054 Uiso 1 1 calc R . .
H3B H 0.7136 0.7834 0.1479 0.054 Uiso 1 1 calc R . .
C4 C 0.7710(2) 0.8506(3) 0.25465(11) 0.0415(5) Uani 1 1 d . . .
C11 C 1.4099(3) 0.9715(6) 0.08698(14) 0.0686(8) Uani 1 1 d . . .
H11A H 1.4260 0.9735 0.1386 0.103 Uiso 1 1 calc R . .
H11B H 1.4608 1.0752 0.0664 0.103 Uiso 1 1 calc R . .
H11C H 1.4513 0.8594 0.0682 0.103 Uiso 1 1 calc R . .
C15 C 0.9469(3) 0.3554(4) 0.43921(12) 0.0491(5) Uani 1 1 d . . .
H15A H 1.0141 0.4194 0.4741 0.059 Uiso 1 1 calc R . .
H15B H 0.9778 0.2269 0.4385 0.059 Uiso 1 1 calc R . .
C14 C 0.7833(2) 0.3689(4) 0.46181(11) 0.0435(5) Uani 1 1 d . . .
C6 C 1.0409(3) 0.9004(4) 0.30910(12) 0.0489(6) Uani 1 1 d . . .
H6A H 1.0717 0.8034 0.2766 0.059 Uiso 1 1 calc R . .
H6B H 1.1222 0.9921 0.3120 0.059 Uiso 1 1 calc R . .
C5 C 0.8935(3) 0.9884(3) 0.27955(10) 0.0398(5) Uani 1 1 d . . .
N3 N 0.4524(4) 0.8672(6) 0.3490(2) 0.1189(14) Uani 1 1 d . . .
O8 O 0.0384(2) 0.4534(3) 0.17309(9) 0.0480(4) Uani 1 1 d . . .
H2 H 0.776(2) 1.088(3) 0.1302(11) 0.036(5) Uiso 1 1 d . . .
H4 H 0.777(2) 0.746(4) 0.2814(12) 0.035(5) Uiso 1 1 d . . .
H5 H 0.860(2) 1.067(3) 0.3121(11) 0.031(5) Uiso 1 1 d . . .
H12 H 0.461(2) 0.224(3) 0.4180(11) 0.026(5) Uiso 1 1 d . . .
H14 H 0.781(3) 0.319(3) 0.5141(13) 0.043(6) Uiso 1 1 d . . .
H5N H 1.006(3) 0.980(4) -0.0675(14) 0.047(7) Uiso 1 1 d . . .
H8NA H 0.502(4) 0.473(4) 0.0905(14) 0.058(8) Uiso 1 1 d . . .
H8NB H 0.335(4) 0.474(4) 0.1006(15) 0.057(8) Uiso 1 1 d . . .
H2O H 0.984(6) 0.711(9) 0.380(3) 0.15(2) Uiso 1 1 d . . .
H6O H 1.049(4) 0.405(5) 0.3591(17) 0.074(10) Uiso 1 1 d . . .
H8OA H 0.124(4) 0.432(4) 0.1914(14) 0.051(7) Uiso 1 1 d . . .
H8OB H 0.005(4) 0.389(5) 0.1986(18) 0.066(10) Uiso 1 1 d . . .


_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
S1 C13 1.803(2) . ?
S1 C14 1.815(3) . ?
N4 C10 1.371(3) . ?
N4 C7 1.376(2) . ?
N4 C2 1.479(2) . ?
O1 C2 1.420(2) . ?
O1 C5 1.449(2) . ?
N5 C8 1.370(3) . ?
N5 C7 1.374(3) . ?
N5 H5N 0.86(3) . ?
O4 C8 1.218(3) . ?
O7 C16 1.237(3) . ?
C16 N7 1.350(3) . ?
C16 N6 1.391(3) . ?
N7 C17 1.334(3) . ?
O5 C12 1.405(2) . ?
O5 C14 1.447(3) . ?
O3 C7 1.212(3) . ?
C2 C3 1.514(3) . ?
C2 H2 0.99(2) . ?
O6 C15 1.421(3) . ?
O6 H6O 0.81(3) . ?
N6 C19 1.364(2) . ?
N6 C12 1.485(2) . ?
C12 C13 1.510(3) . ?
C12 H12 0.97(2) . ?
C19 C18 1.327(3) . ?
C19 H19 0.9300 . ?
C17 N8 1.320(3) . ?
C17 C18 1.421(3) . ?
N1 N2 1.177(3) . ?
N1 C4 1.497(3) . ?
N8 H8NA 0.84(3) . ?
N8 H8NB 0.83(3) . ?
O2 C6 1.408(3) . ?
O2 H2O 0.89(6) . ?
N2 N3 1.127(4) . ?
C8 C9 1.450(3) . ?
C10 C9 1.342(3) . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C9 C11 1.495(3) . ?
C3 C4 1.515(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.517(3) . ?
C4 H4 0.91(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 C14 1.503(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 H14 1.03(2) . ?
C6 C5 1.512(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5 0.89(2) . ?
O8 H8OA 0.82(3) . ?
O8 H8OB 0.73(4) . ?

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
C13 S1 C14 87.38(11) . . ?
C10 N4 C7 121.10(17) . . ?
C10 N4 C2 122.20(15) . . ?
C7 N4 C2 116.50(16) . . ?
C2 O1 C5 110.43(16) . . ?
C8 N5 C7 127.36(17) . . ?
C8 N5 H5N 116.3(16) . . ?
C7 N5 H5N 116.4(16) . . ?
O7 C16 N7 123.00(18) . . ?
O7 C16 N6 117.86(18) . . ?
N7 C16 N6 119.13(17) . . ?
C17 N7 C16 120.25(17) . . ?
C12 O5 C14 113.38(16) . . ?
O1 C2 N4 108.27(16) . . ?
O1 C2 C3 106.42(16) . . ?
N4 C2 C3 113.37(18) . . ?
O1 C2 H2 110.9(13) . . ?
N4 C2 H2 103.4(12) . . ?
C3 C2 H2 114.4(13) . . ?
C15 O6 H6O 104(2) . . ?
C19 N6 C16 120.42(16) . . ?
C19 N6 C12 122.05(15) . . ?
C16 N6 C12 117.53(15) . . ?
O5 C12 N6 108.58(15) . . ?
O5 C12 C13 109.71(17) . . ?
N6 C12 C13 111.90(18) . . ?
O5 C12 H12 108.6(12) . . ?
N6 C12 H12 107.4(12) . . ?
C13 C12 H12 110.5(12) . . ?
C18 C19 N6 120.82(17) . . ?
C18 C19 H19 119.6 . . ?
N6 C19 H19 119.6 . . ?
N8 C17 N7 118.98(19) . . ?
N8 C17 C18 119.89(19) . . ?
N7 C17 C18 121.13(18) . . ?
N2 N1 C4 118.3(2) . . ?
C17 N8 H8NA 116.5(18) . . ?
C17 N8 H8NB 119.1(19) . . ?
H8NA N8 H8NB 124(3) . . ?
C6 O2 H2O 117(3) . . ?
N3 N2 N1 171.9(3) . . ?
O4 C8 N5 119.65(19) . . ?
O4 C8 C9 124.8(2) . . ?
N5 C8 C9 115.56(18) . . ?
C9 C10 N4 124.24(18) . . ?
C9 C10 H10 117.9 . . ?
N4 C10 H10 117.9 . . ?
C19 C18 C17 118.26(17) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
O3 C7 N5 122.60(18) . . ?
O3 C7 N4 122.92(19) . . ?
N5 C7 N4 114.48(18) . . ?
C12 C13 S1 103.66(14) . . ?
C12 C13 H13A 111.0 . . ?
S1 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
S1 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
C10 C9 C8 117.19(19) . . ?
C10 C9 C11 124.8(2) . . ?
C8 C9 C11 118.0(2) . . ?
C2 C3 C4 102.68(18) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C3 107.65(19) . . ?
N1 C4 C5 110.9(2) . . ?
C3 C4 C5 102.66(17) . . ?
N1 C4 H4 110.7(14) . . ?
C3 C4 H4 113.5(15) . . ?
C5 C4 H4 111.2(14) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C15 C14 111.04(18) . . ?
O6 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
O6 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O5 C14 C15 110.84(19) . . ?
O5 C14 S1 106.11(14) . . ?
C15 C14 S1 114.36(19) . . ?
O5 C14 H14 105.6(14) . . ?
C15 C14 H14 107.2(13) . . ?
S1 C14 H14 112.4(14) . . ?
O2 C6 C5 110.6(2) . . ?
O2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
O1 C5 C6 110.02(17) . . ?
O1 C5 C4 105.08(16) . . ?
C6 C5 C4 113.9(2) . . ?
O1 C5 H5 106.4(13) . . ?
C6 C5 H5 108.7(13) . . ?
C4 C5 H5 112.5(13) . . ?
H8OA O8 H8OB 89(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.06
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047


