# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name S.Price _publ_contact_author_address ; Dept of Chemistry University College London 20 Gordon Street LONDON WC1H 0AJ UNITED KINGDOM ; _publ_section_title ; Racemic Progesterone: Predicted in silico and produced in the solid state ; loop_ _publ_author_name _publ_author_address _publ_author_footnote A.T.Hulme ; Christopher Ingold Laboratory Dept. of Chemistry 20 Gordon St. London WC1H 0AJ ; ; ? ; R.W.Lancaster ; Christopher Ingold Laboratory Dept. of Chemistry 20 Gordon St. London WC1H 0AJ ; ; ? ; D.A.Tocher ; Christopher Ingold Laboratory Dept. of Chemistry 20 Gordon St. London WC1H 0AJ ; ; ? ; #============================================================================ # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; The authors acknowledge the Research Councils UK Basic Technology Programme for supporting "Control and Prediction of the Organic Solid State". www.cposs.org.uk ; _publ_section_figure_captions ; ? ; _publ_section_exptl_prep ; Crystals were grown by solvent evaporation from dichloromethane in an NMR tube ; _publ_section_references ; Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Gottingen, Germany. ; _publ_section_exptl_refinement ; All non-hydrogen atoms were refined with an anisotropic model. All H atoms were located in the difference map and were refined isotropically. ; _publ_contact_author_email S.L.PRICE@UCL.AC.UK #========================================================================== data_str0450 _database_code_depnum_ccdc_archive 'CCDC 606954' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'racemic progesterone' _chemical_melting_point '175 degC' _chemical_formula_moiety 'C21 H30 O2' _chemical_formula_sum 'C21 H30 O2' _chemical_formula_weight 314.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9219(17) _cell_length_b 7.4400(12) _cell_length_c 21.034(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.362(3) _cell_angle_gamma 90.00 _cell_volume 1706.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2732 _cell_measurement_theta_min 2.904 _cell_measurement_theta_max 28.259 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.612 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13774 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0825 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3984 _reflns_number_gt 2687 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+1.9254P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3984 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1265 _refine_ls_R_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.1750 _refine_ls_wR_factor_gt 0.1636 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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 O3 O 0.1549(2) 0.4276(3) 0.54819(10) 0.0377(6) Uani 1 1 d . . . O20 O 0.3455(2) 0.4828(3) 0.00122(10) 0.0336(6) Uani 1 1 d . . . C1 C 0.1626(3) 0.2780(4) 0.38497(14) 0.0234(6) Uani 1 1 d . . . H1A H 0.250(3) 0.248(4) 0.3911(14) 0.029(8) Uiso 1 1 d . . . H1B H 0.127(3) 0.180(4) 0.3583(14) 0.029(8) Uiso 1 1 d . . . C2 C 0.1037(3) 0.2823(4) 0.44887(15) 0.0285(7) Uani 1 1 d . . . H2A H 0.014(3) 0.304(4) 0.4444(13) 0.025(8) Uiso 1 1 d . . . H2B H 0.119(3) 0.177(4) 0.4700(14) 0.029(9) Uiso 1 1 d . . . C3 C 0.1515(3) 0.4342(4) 0.48994(14) 0.0268(7) Uani 1 1 d . . . C4 C 0.1874(3) 0.5966(4) 0.45653(14) 0.0277(7) Uani 1 1 d . . . H4A H 0.208(3) 0.697(4) 0.4835(15) 0.037(9) Uiso 1 1 d . . . C5 C 0.1832(2) 0.6128(4) 0.39297(14) 0.0223(6) Uani 1 1 d . . . C6 C 0.2059(3) 0.7916(4) 0.36282(15) 0.0302(7) Uani 1 1 d . . . H6A H 0.234(3) 0.875(4) 0.3961(15) 0.032(9) Uiso 1 1 d . . . H6B H 0.125(3) 0.832(4) 0.3459(14) 0.031(9) Uiso 1 1 d . . . C7 C 0.2940(3) 0.7793(4) 0.30983(15) 0.0287(7) Uani 1 1 d . . . H7A H 0.376(3) 0.745(4) 0.3272(13) 0.018(7) Uiso 1 1 d . . . H7B H 0.299(3) 0.891(5) 0.2898(14) 0.032(9) Uiso 1 1 d . . . C8 C 0.2527(3) 0.6396(4) 0.26022(13) 0.0193(6) Uani 1 1 d . . . H8A H 0.170(3) 0.673(4) 0.2421(13) 0.020(7) Uiso 1 1 d . . . C9 C 0.2412(3) 0.4548(4) 0.29340(13) 0.0193(6) Uani 1 1 d . . . H9A H 0.324(3) 0.432(4) 0.3133(13) 0.023(8) Uiso 1 1 d . . . C10 C 0.1508(2) 0.4563(4) 0.34818(13) 0.0198(6) Uani 1 1 d . . . C11 C 0.2124(3) 0.3051(4) 0.24453(14) 0.0249(7) Uani 1 1 d . . . H11A H 0.213(3) 0.190(4) 0.2655(14) 0.026(8) Uiso 1 1 d . . . H11B H 0.128(3) 0.319(4) 0.2262(14) 0.028(8) Uiso 1 1 d . . . C12 C 0.3001(3) 0.2990(4) 0.19058(14) 0.0248(7) Uani 1 1 d . . . H12A H 0.386(3) 0.266(4) 0.2080(14) 0.031(8) Uiso 1 1 d . . . H12B H 0.278(3) 0.204(4) 0.1604(15) 0.034(9) Uiso 1 1 d . . . C13 C 0.3051(3) 0.4805(4) 0.15702(13) 0.0204(6) Uani 1 1 d . . . C14 C 0.3410(3) 0.6245(4) 0.20744(13) 0.0206(6) Uani 1 1 d . . . H14A H 0.419(3) 0.582(4) 0.2278(13) 0.021(7) Uiso 1 1 d . . . C15 C 0.3679(3) 0.7917(4) 0.16804(15) 0.0271(7) Uani 1 1 d . . . H15A H 0.424(3) 0.875(5) 0.1902(15) 0.037(9) Uiso 1 1 d . . . H15B H 0.293(3) 0.857(4) 0.1582(14) 0.029(9) Uiso 1 1 d . . . C16 C 0.4229(3) 0.7143(4) 0.10756(15) 0.0271(7) Uani 1 1 d . . . H16A H 0.509(3) 0.747(4) 0.1052(13) 0.021(8) Uiso 1 1 d . . . H16B H 0.381(3) 0.761(4) 0.0684(15) 0.030(8) Uiso 1 1 d . . . C17 C 0.4107(3) 0.5095(4) 0.11155(13) 0.0220(6) Uani 1 1 d . . . H17A H 0.483(3) 0.460(4) 0.1323(13) 0.018(7) Uiso 1 1 d . . . C18 C 0.1812(3) 0.5213(5) 0.12103(15) 0.0253(7) Uani 1 1 d . . . H18A H 0.157(3) 0.423(4) 0.0911(15) 0.034(9) Uiso 1 1 d . . . H18B H 0.115(3) 0.540(4) 0.1501(14) 0.023(8) Uiso 1 1 d . . . H18C H 0.183(3) 0.639(5) 0.0962(15) 0.038(9) Uiso 1 1 d . . . C19 C 0.0167(3) 0.4820(5) 0.32227(15) 0.0266(7) Uani 1 1 d . . . H19A H -0.036(3) 0.504(4) 0.3571(15) 0.030(9) Uiso 1 1 d . . . H19B H 0.010(3) 0.583(5) 0.2932(15) 0.036(9) Uiso 1 1 d . . . H19C H -0.009(3) 0.379(5) 0.2968(16) 0.045(10) Uiso 1 1 d . . . C20 C 0.3939(3) 0.4125(4) 0.04848(14) 0.0253(7) Uani 1 1 d . . . C21 C 0.4411(3) 0.2233(5) 0.04643(17) 0.0313(7) Uani 1 1 d . . . H21A H 0.415(3) 0.155(4) 0.0823(16) 0.035(9) Uiso 1 1 d . . . H21B H 0.531(4) 0.231(5) 0.0510(16) 0.049(10) Uiso 1 1 d . . . H21C H 0.414(3) 0.168(5) 0.0065(18) 0.049(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0381(14) 0.0508(15) 0.0252(12) 0.0026(10) 0.0091(10) 0.0067(11) O20 0.0316(13) 0.0406(14) 0.0284(11) 0.0043(10) 0.0001(9) 0.0010(10) C1 0.0228(16) 0.0192(15) 0.0285(16) 0.0022(12) 0.0036(12) 0.0028(13) C2 0.0264(18) 0.0255(17) 0.0339(17) 0.0075(14) 0.0058(13) 0.0036(14) C3 0.0162(15) 0.0359(18) 0.0291(16) 0.0028(13) 0.0073(12) 0.0118(13) C4 0.0244(17) 0.0310(18) 0.0281(16) -0.0062(13) 0.0029(13) 0.0014(14) C5 0.0137(14) 0.0225(15) 0.0307(15) -0.0038(12) 0.0014(11) 0.0039(11) C6 0.041(2) 0.0195(16) 0.0302(17) -0.0052(13) 0.0014(15) 0.0006(15) C7 0.039(2) 0.0160(16) 0.0308(16) -0.0011(13) -0.0036(14) -0.0050(14) C8 0.0181(15) 0.0148(14) 0.0244(14) 0.0013(11) -0.0036(11) -0.0014(11) C9 0.0165(14) 0.0160(14) 0.0249(14) 0.0002(11) -0.0023(11) 0.0004(11) C10 0.0158(14) 0.0174(14) 0.0261(14) -0.0008(11) 0.0006(11) 0.0006(11) C11 0.0289(17) 0.0161(15) 0.0302(16) -0.0005(12) 0.0062(13) -0.0019(13) C12 0.0298(17) 0.0163(15) 0.0287(16) -0.0024(12) 0.0059(13) 0.0006(13) C13 0.0194(15) 0.0177(14) 0.0239(14) -0.0001(11) 0.0008(11) 0.0011(11) C14 0.0148(14) 0.0177(14) 0.0286(15) 0.0027(12) -0.0039(11) -0.0003(11) C15 0.0271(17) 0.0203(16) 0.0339(17) 0.0032(13) 0.0013(13) -0.0053(14) C16 0.0247(17) 0.0252(16) 0.0316(17) 0.0044(13) 0.0019(13) -0.0049(14) C17 0.0160(15) 0.0243(16) 0.0256(15) 0.0031(12) -0.0002(12) 0.0034(12) C18 0.0170(15) 0.0310(18) 0.0278(16) -0.0023(14) -0.0005(12) 0.0015(13) C19 0.0217(16) 0.0302(18) 0.0277(16) -0.0001(14) 0.0001(13) 0.0016(14) C20 0.0177(15) 0.0313(17) 0.0276(16) 0.0025(13) 0.0063(12) -0.0015(13) C21 0.0309(19) 0.0327(19) 0.0311(18) -0.0008(15) 0.0090(14) 0.0005(15) _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 O3 C3 1.225(3) . ? O20 C20 1.216(3) . ? C1 C2 1.524(4) . ? C1 C10 1.537(4) . ? C1 H1A 0.99(3) . ? C1 H1B 0.99(3) . ? C2 C3 1.498(4) . ? C2 H2A 0.99(3) . ? C2 H2B 0.91(3) . ? C3 C4 1.463(4) . ? C4 C5 1.341(4) . ? C4 H4A 0.96(3) . ? C5 C6 1.500(4) . ? C5 C10 1.526(4) . ? C6 C7 1.518(5) . ? C6 H6A 0.97(3) . ? C6 H6B 0.98(3) . ? C7 C8 1.522(4) . ? C7 H7A 0.98(3) . ? C7 H7B 0.94(3) . ? C8 C14 1.516(4) . ? C8 C9 1.550(4) . ? C8 H8A 1.00(3) . ? C9 C11 1.536(4) . ? C9 C10 1.561(4) . ? C9 H9A 0.99(3) . ? C10 C19 1.544(4) . ? C11 C12 1.529(4) . ? C11 H11A 0.97(3) . ? C11 H11B 0.99(3) . ? C12 C13 1.527(4) . ? C12 H12A 1.01(3) . ? C12 H12B 0.97(3) . ? C13 C18 1.541(4) . ? C13 C14 1.542(4) . ? C13 C17 1.556(4) . ? C14 C15 1.533(4) . ? C14 H14A 0.99(3) . ? C15 C16 1.549(4) . ? C15 H15A 0.97(3) . ? C15 H15B 0.97(3) . ? C16 C17 1.532(4) . ? C16 H16A 0.97(3) . ? C16 H16B 0.98(3) . ? C17 C20 1.512(4) . ? C17 H17A 0.95(3) . ? C18 H18A 0.99(3) . ? C18 H18B 0.98(3) . ? C18 H18C 1.02(3) . ? C19 H19A 0.98(3) . ? C19 H19B 0.97(3) . ? C19 H19C 0.97(4) . ? C20 C21 1.501(5) . ? C21 H21A 0.97(3) . ? C21 H21B 0.98(4) . ? C21 H21C 0.97(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 C2 C1 C10 113.5(3) . . ? C2 C1 H1A 110.3(17) . . ? C10 C1 H1A 108.2(18) . . ? C2 C1 H1B 110.1(18) . . ? C10 C1 H1B 109.5(17) . . ? H1A C1 H1B 105(2) . . ? C3 C2 C1 111.9(3) . . ? C3 C2 H2A 104.0(17) . . ? C1 C2 H2A 112.7(17) . . ? C3 C2 H2B 108.7(19) . . ? C1 C2 H2B 110(2) . . ? H2A C2 H2B 110(3) . . ? O3 C3 C4 121.4(3) . . ? O3 C3 C2 122.4(3) . . ? C4 C3 C2 116.1(3) . . ? C5 C4 C3 124.0(3) . . ? C5 C4 H4A 121(2) . . ? C3 C4 H4A 115(2) . . ? C4 C5 C6 120.3(3) . . ? C4 C5 C10 122.7(3) . . ? C6 C5 C10 117.0(2) . . ? C5 C6 C7 112.6(3) . . ? C5 C6 H6A 108.2(18) . . ? C7 C6 H6A 112.2(19) . . ? C5 C6 H6B 105.0(19) . . ? C7 C6 H6B 110.4(18) . . ? H6A C6 H6B 108(3) . . ? C6 C7 C8 111.7(3) . . ? C6 C7 H7A 110.3(16) . . ? C8 C7 H7A 107.7(16) . . ? C6 C7 H7B 110(2) . . ? C8 C7 H7B 108.7(19) . . ? H7A C7 H7B 109(3) . . ? C14 C8 C7 112.2(2) . . ? C14 C8 C9 109.6(2) . . ? C7 C8 C9 109.0(2) . . ? C14 C8 H8A 110.0(16) . . ? C7 C8 H8A 108.8(16) . . ? C9 C8 H8A 107.2(16) . . ? C11 C9 C8 111.2(2) . . ? C11 C9 C10 112.7(2) . . ? C8 C9 C10 113.4(2) . . ? C11 C9 H9A 107.8(17) . . ? C8 C9 H9A 104.2(17) . . ? C10 C9 H9A 107.0(16) . . ? C5 C10 C1 109.7(2) . . ? C5 C10 C19 107.7(2) . . ? C1 C10 C19 109.6(2) . . ? C5 C10 C9 109.1(2) . . ? C1 C10 C9 109.1(2) . . ? C19 C10 C9 111.6(2) . . ? C12 C11 C9 113.9(3) . . ? C12 C11 H11A 109.0(18) . . ? C9 C11 H11A 110.1(17) . . ? C12 C11 H11B 109.1(17) . . ? C9 C11 H11B 109.5(17) . . ? H11A C11 H11B 105(2) . . ? C13 C12 C11 110.9(2) . . ? C13 C12 H12A 108.7(18) . . ? C11 C12 H12A 110.1(17) . . ? C13 C12 H12B 110.7(19) . . ? C11 C12 H12B 111.4(19) . . ? H12A C12 H12B 105(2) . . ? C12 C13 C18 110.3(2) . . ? C12 C13 C14 108.1(2) . . ? C18 C13 C14 112.4(2) . . ? C12 C13 C17 117.0(2) . . ? C18 C13 C17 109.4(2) . . ? C14 C13 C17 99.1(2) . . ? C8 C14 C15 119.1(2) . . ? C8 C14 C13 114.1(2) . . ? C15 C14 C13 103.9(2) . . ? C8 C14 H14A 106.1(16) . . ? C15 C14 H14A 107.9(17) . . ? C13 C14 H14A 104.7(16) . . ? C14 C15 C16 103.8(2) . . ? C14 C15 H15A 113.3(19) . . ? C16 C15 H15A 112(2) . . ? C14 C15 H15B 109.5(19) . . ? C16 C15 H15B 112.1(18) . . ? H15A C15 H15B 107(3) . . ? C17 C16 C15 106.6(2) . . ? C17 C16 H16A 109.9(17) . . ? C15 C16 H16A 111.7(17) . . ? C17 C16 H16B 111.2(18) . . ? C15 C16 H16B 111.8(18) . . ? H16A C16 H16B 106(2) . . ? C20 C17 C16 115.7(2) . . ? C20 C17 C13 114.6(2) . . ? C16 C17 C13 104.0(2) . . ? C20 C17 H17A 105.8(16) . . ? C16 C17 H17A 109.6(17) . . ? C13 C17 H17A 106.9(17) . . ? C13 C18 H18A 111.1(18) . . ? C13 C18 H18B 112.1(16) . . ? H18A C18 H18B 109(3) . . ? C13 C18 H18C 112.0(18) . . ? H18A C18 H18C 109(2) . . ? H18B C18 H18C 104(2) . . ? C10 C19 H19A 110.5(18) . . ? C10 C19 H19B 111(2) . . ? H19A C19 H19B 109(3) . . ? C10 C19 H19C 110(2) . . ? H19A C19 H19C 113(3) . . ? H19B C19 H19C 105(3) . . ? O20 C20 C21 120.9(3) . . ? O20 C20 C17 122.4(3) . . ? C21 C20 C17 116.7(3) . . ? C20 C21 H21A 111(2) . . ? C20 C21 H21B 106(2) . . ? H21A C21 H21B 107(3) . . ? C20 C21 H21C 110(2) . . ? H21A C21 H21C 111(3) . . ? H21B C21 H21C 111(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 C1 C2 C3 -54.6(3) . . . . ? C1 C2 C3 O3 -152.0(3) . . . . ? C1 C2 C3 C4 31.5(4) . . . . ? O3 C3 C4 C5 -178.6(3) . . . . ? C2 C3 C4 C5 -2.1(4) . . . . ? C3 C4 C5 C6 171.9(3) . . . . ? C3 C4 C5 C10 -5.6(5) . . . . ? C4 C5 C6 C7 133.3(3) . . . . ? C10 C5 C6 C7 -49.0(4) . . . . ? C5 C6 C7 C8 53.7(4) . . . . ? C6 C7 C8 C14 -179.3(2) . . . . ? C6 C7 C8 C9 -57.7(3) . . . . ? C14 C8 C9 C11 -51.2(3) . . . . ? C7 C8 C9 C11 -174.3(3) . . . . ? C14 C8 C9 C10 -179.3(2) . . . . ? C7 C8 C9 C10 57.5(3) . . . . ? C4 C5 C10 C1 -16.6(4) . . . . ? C6 C5 C10 C1 165.8(3) . . . . ? C4 C5 C10 C19 102.6(3) . . . . ? C6 C5 C10 C19 -74.9(3) . . . . ? C4 C5 C10 C9 -136.1(3) . . . . ? C6 C5 C10 C9 46.4(3) . . . . ? C2 C1 C10 C5 46.0(3) . . . . ? C2 C1 C10 C19 -72.1(3) . . . . ? C2 C1 C10 C9 165.4(2) . . . . ? C11 C9 C10 C5 -178.0(2) . . . . ? C8 C9 C10 C5 -50.6(3) . . . . ? C11 C9 C10 C1 62.2(3) . . . . ? C8 C9 C10 C1 -170.4(2) . . . . ? C11 C9 C10 C19 -59.0(3) . . . . ? C8 C9 C10 C19 68.4(3) . . . . ? C8 C9 C11 C12 52.0(3) . . . . ? C10 C9 C11 C12 -179.4(2) . . . . ? C9 C11 C12 C13 -55.1(3) . . . . ? C11 C12 C13 C18 -67.4(3) . . . . ? C11 C12 C13 C14 55.9(3) . . . . ? C11 C12 C13 C17 166.7(2) . . . . ? C7 C8 C14 C15 -58.3(3) . . . . ? C9 C8 C14 C15 -179.5(2) . . . . ? C7 C8 C14 C13 178.3(2) . . . . ? C9 C8 C14 C13 57.1(3) . . . . ? C12 C13 C14 C8 -59.5(3) . . . . ? C18 C13 C14 C8 62.6(3) . . . . ? C17 C13 C14 C8 178.1(2) . . . . ? C12 C13 C14 C15 169.3(2) . . . . ? C18 C13 C14 C15 -68.7(3) . . . . ? C17 C13 C14 C15 46.8(3) . . . . ? C8 C14 C15 C16 -161.8(2) . . . . ? C13 C14 C15 C16 -33.6(3) . . . . ? C14 C15 C16 C17 6.5(3) . . . . ? C15 C16 C17 C20 149.1(3) . . . . ? C15 C16 C17 C13 22.5(3) . . . . ? C12 C13 C17 C20 74.8(3) . . . . ? C18 C13 C17 C20 -51.6(3) . . . . ? C14 C13 C17 C20 -169.4(2) . . . . ? C12 C13 C17 C16 -157.9(2) . . . . ? C18 C13 C17 C16 75.7(3) . . . . ? C14 C13 C17 C16 -42.1(3) . . . . ? C16 C17 C20 O20 -28.3(4) . . . . ? C13 C17 C20 O20 92.7(3) . . . . ? C16 C17 C20 C21 151.2(3) . . . . ? C13 C17 C20 C21 -87.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.290 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.056 # start Validation Reply Form #_vrf_DIFF020_str0450 #; #PROBLEM: _diffrn_standards_interval_count and #RESPONSE: Area detector used #; # end Validation Reply Form