Electronic Supplementary Material for CrystEngComm This journal is (c) the Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 #============================================================================ # 1. SUBMISSION DETAILS _publ_contact_author_name 'Ashley Hulme' _publ_contact_author_address ; Christopher Ingold Laboratory Dept. of Chemistry University College London 20 Gordon St. London WC1H 0AJ ; _publ_contact_letter ; ? ; _publ_contact_author_phone ? _publ_contact_author_fax ? _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_author_email A.HULME@UCL.AC.UK _publ_section_title ; Clarification of the Crystalline Forms of Androsterone ; loop_ _publ_author_name _publ_author_address _publ_author_footnote A.T.Hulme ; Christopher Ingold Laboratory Dept. of Chemistry University College London 20 Gordon St. London WC1H 0AJ ; ; ? ; R.W.Lancaster ; Christopher Ingold Laboratory Dept. of Chemistry University College London 20 Gordon St. London WC1H 0AJ ; ; ? ; H.F.Cannon ; ? ; ; ? ; _vrf_DIFF020_str0313 ; PROBLEM: _diffrn_standards_interval_count and RESPONSE: Area detector used ; _vrf_PLAT035_str0313 ; PROBLEM: No _chemical_absolute_configuration info given . RESPONSE: Light atom structure - Flack parameter meaningless, consequently the absolute configuration cannot be deduced. ; # end Validation Reply Form _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 H atoms were located in a difference map and were refined isotropically. ; #========================================================================== data_str0313 _database_code_depnum_ccdc_archive 'CCDC 293344' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19 H30 O2), H2 O' _chemical_formula_sum 'C38 H62 O5' _chemical_formula_weight 598.88 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 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.4288(8) _cell_length_b 10.2892(11) _cell_length_c 22.174(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.553(2) _cell_angle_gamma 90.00 _cell_volume 1680.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2357 _cell_measurement_theta_min 2.7025 _cell_measurement_theta_max 22.3765 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9551 _exptl_absorpt_correction_T_max 0.9907 _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 15001 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4268 _reflns_number_gt 3663 _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^)+(0.0531P)^2^+0.3710P] 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_abs_structure_details #'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack 0.5(14) _refine_ls_number_reflns 4268 _refine_ls_number_parameters 636 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 O90 O 0.2295(4) 0.8584(3) 0.70465(12) 0.0417(6) Uani 1 1 d . . . H90 H 0.323(9) 0.772(7) 0.721(3) 0.13(2) Uiso 1 1 d . . . H91 H 0.327(8) 0.924(7) 0.688(3) 0.11(2) Uiso 1 1 d . . . O52 O 0.5013(4) 1.0329(3) 0.69126(10) 0.0418(6) Uani 1 1 d . . . O51 O 0.5644(3) 1.1336(2) 0.26715(10) 0.0326(5) Uani 1 1 d . . . H51 H 0.456(5) 1.135(4) 0.2544(15) 0.030(9) Uiso 1 1 d . . . C68 C 0.7065(6) 0.8169(3) 0.62106(17) 0.0388(8) Uani 1 1 d . . . H68A H 0.622(5) 0.769(4) 0.6428(18) 0.045(11) Uiso 1 1 d . . . H68B H 0.825(5) 0.825(4) 0.6440(17) 0.042(10) Uiso 1 1 d . . . H68C H 0.723(4) 0.767(4) 0.5846(16) 0.034(9) Uiso 1 1 d . . . C69 C 0.7031(5) 0.7887(3) 0.40372(16) 0.0313(7) Uani 1 1 d . . . H69A H 0.604(6) 0.733(5) 0.4118(19) 0.058(13) Uiso 1 1 d . . . H69B H 0.738(5) 0.764(4) 0.3650(17) 0.037(10) Uiso 1 1 d . . . H69C H 0.800(5) 0.773(4) 0.4355(18) 0.048(11) Uiso 1 1 d . . . C67 C 0.6267(5) 1.0250(3) 0.66159(13) 0.0307(7) Uani 1 1 d . . . C66 C 0.8092(5) 1.0904(4) 0.67709(15) 0.0383(8) Uani 1 1 d . . . H66A H 0.785(5) 1.181(5) 0.6864(18) 0.056(12) Uiso 1 1 d . . . H66B H 0.873(5) 1.056(4) 0.7160(16) 0.045(10) Uiso 1 1 d . . . C65 C 0.9095(5) 1.0711(4) 0.62209(15) 0.0386(8) Uani 1 1 d . . . H65A H 0.971(5) 1.151(4) 0.6134(16) 0.044(10) Uiso 1 1 d . . . H65B H 0.992(4) 1.000(4) 0.6269(14) 0.025(8) Uiso 1 1 d . . . C64 C 0.7549(4) 1.0395(3) 0.57123(13) 0.0264(6) Uani 1 1 d . . . H64A H 0.689(4) 1.122(4) 0.5632(14) 0.026(8) Uiso 1 1 d . . . C63 C 0.6262(4) 0.9512(3) 0.60205(13) 0.0264(6) Uani 1 1 d . . . C62 C 0.4459(4) 0.9381(3) 0.56163(14) 0.0278(7) Uani 1 1 d . . . H62A H 0.384(4) 1.023(4) 0.5584(14) 0.025(8) Uiso 1 1 d . . . H62B H 0.369(4) 0.882(3) 0.5803(14) 0.022(8) Uiso 1 1 d . . . C61 C 0.4755(4) 0.8917(3) 0.49790(14) 0.0261(6) Uani 1 1 d . . . H61A H 0.530(4) 0.801(4) 0.4999(16) 0.030(9) Uiso 1 1 d . . . H61B H 0.362(4) 0.889(4) 0.4718(14) 0.030(9) Uiso 1 1 d . . . C60 C 0.6385(4) 0.9305(3) 0.40281(13) 0.0223(6) Uani 1 1 d . . . C59 C 0.6132(4) 0.9746(3) 0.46808(13) 0.0209(6) Uani 1 1 d . . . H59A H 0.559(4) 1.060(3) 0.4646(13) 0.019(7) Uiso 1 1 d . . . C58 C 0.7949(4) 0.9873(3) 0.51051(14) 0.0265(6) Uani 1 1 d . . . H58A H 0.849(4) 0.897(4) 0.5160(14) 0.025(8) Uiso 1 1 d . . . C57 C 0.9307(5) 1.0725(4) 0.48247(16) 0.0363(8) Uani 1 1 d . . . H57A H 0.881(5) 1.163(4) 0.4816(16) 0.039(10) Uiso 1 1 d . . . H57B H 1.048(5) 1.071(4) 0.5088(16) 0.036(9) Uiso 1 1 d . . . C56 C 0.9564(4) 1.0290(4) 0.41898(16) 0.0382(8) Uani 1 1 d . . . H56A H 1.036(5) 1.093(4) 0.4018(18) 0.048(11) Uiso 1 1 d . . . H56B H 1.009(6) 0.942(5) 0.420(2) 0.065(14) Uiso 1 1 d . . . C55 C 0.7746(4) 1.0240(3) 0.37778(13) 0.0264(6) Uani 1 1 d . . . H55A H 0.722(4) 1.111(3) 0.3801(13) 0.019(8) Uiso 1 1 d . . . C54 C 0.7990(4) 0.9954(4) 0.31179(14) 0.0309(7) Uani 1 1 d . . . H54A H 0.883(4) 1.060(3) 0.2997(14) 0.025(8) Uiso 1 1 d . . . H54B H 0.859(4) 0.913(4) 0.3072(15) 0.032(9) Uiso 1 1 d . . . C53 C 0.6206(4) 1.0000(3) 0.26995(14) 0.0294(7) Uani 1 1 d . . . H53A H 0.639(4) 0.972(3) 0.2283(14) 0.024(8) Uiso 1 1 d . . . C52 C 0.4786(4) 0.9136(3) 0.29327(14) 0.0273(6) Uani 1 1 d . . . H52A H 0.360(5) 0.929(4) 0.2676(15) 0.033(9) Uiso 1 1 d . . . H52B H 0.515(5) 0.820(4) 0.2894(16) 0.043(10) Uiso 1 1 d . . . C51 C 0.4577(4) 0.9410(3) 0.35995(13) 0.0237(6) Uani 1 1 d . . . H51A H 0.362(4) 0.879(3) 0.3734(12) 0.011(7) Uiso 1 1 d . . . H51B H 0.404(4) 1.024(4) 0.3638(13) 0.023(8) Uiso 1 1 d . . . O2 O 0.1999(3) 0.1363(3) 0.22293(10) 0.0416(6) Uani 1 1 d . . . O1 O 0.1392(3) 0.0269(2) -0.20294(10) 0.0346(5) Uani 1 1 d . . . H1 H 0.182(5) -0.024(4) -0.2300(17) 0.041(11) Uiso 1 1 d . . . C18 C 0.2510(5) 0.3765(3) 0.13950(14) 0.0280(6) Uani 1 1 d . . . H18A H 0.351(5) 0.372(4) 0.1723(16) 0.041(10) Uiso 1 1 d . . . H18B H 0.160(5) 0.423(4) 0.1530(16) 0.036(9) Uiso 1 1 d . . . H18C H 0.282(4) 0.429(3) 0.1030(14) 0.023(8) Uiso 1 1 d . . . C19 C 0.3192(4) 0.3826(3) -0.07584(14) 0.0253(6) Uani 1 1 d . . . H19A H 0.331(4) 0.410(4) -0.1181(15) 0.031(9) Uiso 1 1 d . . . H19B H 0.250(4) 0.448(3) -0.0558(14) 0.024(8) Uiso 1 1 d . . . H19C H 0.438(5) 0.389(4) -0.0531(15) 0.035(9) Uiso 1 1 d . . . C17 C 0.1160(4) 0.1855(3) 0.17832(13) 0.0268(6) Uani 1 1 d . . . C16 C -0.0876(4) 0.2078(4) 0.16975(15) 0.0311(7) Uani 1 1 d . . . H16A H -0.110(5) 0.257(4) 0.2039(16) 0.031(9) Uiso 1 1 d . . . H16B H -0.143(5) 0.121(4) 0.1699(16) 0.037(10) Uiso 1 1 d . . . C15 C -0.1320(4) 0.2725(3) 0.10718(14) 0.0272(6) Uani 1 1 d . . . H15A H -0.253(4) 0.246(3) 0.0869(14) 0.020(8) Uiso 1 1 d . . . H15B H -0.137(4) 0.368(4) 0.1124(14) 0.026(8) Uiso 1 1 d . . . C14 C 0.0250(3) 0.2258(3) 0.07455(13) 0.0207(6) Uani 1 1 d . . . H14A H 0.004(4) 0.135(3) 0.0675(12) 0.015(7) Uiso 1 1 d . . . C13 C 0.1932(4) 0.2354(3) 0.12254(13) 0.0212(6) Uani 1 1 d . . . C12 C 0.3483(4) 0.1589(3) 0.10114(13) 0.0243(6) Uani 1 1 d . . . H12A H 0.321(4) 0.058(4) 0.0989(15) 0.037(10) Uiso 1 1 d . . . H12B H 0.454(4) 0.168(3) 0.1309(14) 0.025(8) Uiso 1 1 d . . . C11 C 0.3818(3) 0.2054(3) 0.03758(12) 0.0225(6) Uani 1 1 d . . . H11A H 0.434(4) 0.292(3) 0.0402(13) 0.023(8) Uiso 1 1 d . . . H11B H 0.475(5) 0.151(4) 0.0233(14) 0.035(9) Uiso 1 1 d . . . C10 C 0.2431(4) 0.2431(3) -0.07509(12) 0.0200(6) Uani 1 1 d . . . C9 C 0.2107(4) 0.2038(3) -0.00992(12) 0.0201(6) Uani 1 1 d . . . H9A H 0.167(4) 0.113(3) -0.0139(13) 0.015(7) Uiso 1 1 d . . . C8 C 0.0535(3) 0.2808(3) 0.01291(12) 0.0199(5) Uani 1 1 d . . . H8A H 0.088(4) 0.374(3) 0.0167(13) 0.019(7) Uiso 1 1 d . . . C7 C -0.1209(4) 0.2735(3) -0.03184(13) 0.0260(6) Uani 1 1 d . . . H7A H -0.166(4) 0.184(4) -0.0321(14) 0.026(8) Uiso 1 1 d . . . H7B H -0.212(4) 0.330(3) -0.0191(12) 0.010(6) Uiso 1 1 d . . . C6 C -0.0897(4) 0.3099(3) -0.09629(13) 0.0256(6) Uani 1 1 d . . . H6A H -0.062(4) 0.408(3) -0.0988(13) 0.019(7) Uiso 1 1 d . . . H6B H -0.200(5) 0.297(4) -0.1226(16) 0.033(9) Uiso 1 1 d . . . C5 C 0.0604(4) 0.2276(3) -0.11704(12) 0.0209(6) Uani 1 1 d . . . H5A H 0.029(4) 0.136(3) -0.1128(12) 0.014(7) Uiso 1 1 d . . . C4 C 0.0781(4) 0.2487(3) -0.18423(13) 0.0262(6) Uani 1 1 d . . . H4A H -0.034(4) 0.233(3) -0.2068(14) 0.022(8) Uiso 1 1 d . . . H4B H 0.115(4) 0.342(3) -0.1885(14) 0.024(8) Uiso 1 1 d . . . C3 C 0.2137(4) 0.1548(3) -0.20617(13) 0.0289(7) Uani 1 1 d . . . H3A H 0.221(4) 0.175(3) -0.2487(13) 0.018(7) Uiso 1 1 d . . . C2 C 0.3963(4) 0.1657(3) -0.16665(14) 0.0293(7) Uani 1 1 d . . . H2A H 0.452(4) 0.249(4) -0.1722(15) 0.029(9) Uiso 1 1 d . . . H2B H 0.478(4) 0.101(3) -0.1801(14) 0.027(8) Uiso 1 1 d . . . C1 C 0.3809(4) 0.1485(3) -0.09890(13) 0.0239(6) Uani 1 1 d . . . H1A H 0.500(4) 0.161(3) -0.0762(12) 0.014(7) Uiso 1 1 d . . . H1B H 0.337(4) 0.056(3) -0.0900(12) 0.016(7) 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 O90 0.0447(14) 0.0379(14) 0.0453(14) 0.0013(11) 0.0160(11) 0.0047(12) O52 0.0548(15) 0.0421(14) 0.0293(11) -0.0060(11) 0.0088(10) -0.0025(12) O51 0.0338(13) 0.0284(11) 0.0342(12) 0.0040(9) -0.0004(10) -0.0017(10) C68 0.058(2) 0.0242(16) 0.0332(18) 0.0023(14) 0.0032(17) 0.0059(16) C69 0.0407(19) 0.0246(16) 0.0291(17) -0.0001(13) 0.0067(14) 0.0096(14) C67 0.0452(19) 0.0231(14) 0.0227(14) 0.0033(12) 0.0007(13) 0.0023(14) C66 0.049(2) 0.0356(18) 0.0264(16) -0.0009(14) -0.0112(14) -0.0018(16) C65 0.0371(19) 0.043(2) 0.0324(17) 0.0009(15) -0.0080(14) -0.0094(17) C64 0.0272(15) 0.0243(15) 0.0254(14) 0.0019(12) -0.0052(11) -0.0019(13) C63 0.0353(17) 0.0223(14) 0.0210(14) 0.0006(11) 0.0016(12) 0.0008(12) C62 0.0324(17) 0.0249(15) 0.0265(16) -0.0021(12) 0.0050(13) -0.0049(13) C61 0.0276(16) 0.0251(15) 0.0250(14) -0.0045(12) 0.0013(12) -0.0062(13) C60 0.0222(14) 0.0188(13) 0.0259(15) -0.0012(11) 0.0029(11) 0.0023(11) C59 0.0205(14) 0.0162(13) 0.0253(14) 0.0001(11) 0.0000(11) 0.0019(11) C58 0.0243(14) 0.0250(15) 0.0284(15) 0.0008(12) -0.0031(11) 0.0002(12) C57 0.0243(16) 0.048(2) 0.0335(17) 0.0032(15) -0.0059(13) -0.0106(15) C56 0.0222(16) 0.053(2) 0.0395(18) 0.0065(17) 0.0041(13) -0.0053(16) C55 0.0211(15) 0.0270(15) 0.0309(15) 0.0022(13) 0.0021(11) 0.0017(12) C54 0.0285(17) 0.0341(18) 0.0310(16) 0.0029(14) 0.0074(13) 0.0038(14) C53 0.0358(17) 0.0290(16) 0.0245(15) 0.0000(12) 0.0075(12) 0.0025(13) C52 0.0314(16) 0.0259(16) 0.0235(15) -0.0048(12) -0.0004(12) 0.0001(13) C51 0.0217(14) 0.0231(14) 0.0262(15) -0.0025(12) 0.0027(11) -0.0021(12) O2 0.0346(12) 0.0604(16) 0.0294(12) 0.0185(11) 0.0030(9) 0.0041(12) O1 0.0471(14) 0.0289(11) 0.0280(11) -0.0065(10) 0.0053(10) 0.0006(10) C18 0.0299(16) 0.0266(15) 0.0265(16) -0.0011(13) 0.0000(13) -0.0046(13) C19 0.0276(16) 0.0236(14) 0.0242(15) 0.0007(12) 0.0017(12) -0.0048(12) C17 0.0286(15) 0.0269(15) 0.0250(15) 0.0001(12) 0.0042(11) -0.0025(12) C16 0.0282(16) 0.0378(19) 0.0285(16) 0.0005(14) 0.0086(12) -0.0010(14) C15 0.0173(14) 0.0351(17) 0.0291(15) -0.0008(13) 0.0027(11) 0.0012(12) C14 0.0146(13) 0.0214(14) 0.0254(15) -0.0007(11) 0.0003(10) -0.0011(11) C13 0.0171(13) 0.0230(14) 0.0226(14) 0.0014(11) -0.0001(10) -0.0016(11) C12 0.0190(13) 0.0291(16) 0.0235(14) 0.0046(12) -0.0018(11) 0.0016(12) C11 0.0134(13) 0.0306(16) 0.0230(14) 0.0006(12) 0.0007(10) 0.0012(12) C10 0.0165(12) 0.0230(14) 0.0199(13) 0.0004(11) 0.0008(10) 0.0009(11) C9 0.0177(13) 0.0185(14) 0.0237(14) 0.0004(11) 0.0019(10) 0.0015(11) C8 0.0159(13) 0.0208(13) 0.0221(14) -0.0007(11) -0.0013(10) -0.0001(11) C7 0.0177(14) 0.0346(17) 0.0248(15) -0.0046(13) -0.0012(11) 0.0060(13) C6 0.0183(14) 0.0297(16) 0.0269(15) -0.0019(12) -0.0044(11) 0.0040(12) C5 0.0221(14) 0.0190(13) 0.0205(14) -0.0009(11) -0.0011(10) -0.0004(11) C4 0.0294(16) 0.0257(16) 0.0215(14) -0.0010(12) -0.0036(12) 0.0016(13) C3 0.0394(17) 0.0269(16) 0.0208(14) 0.0009(12) 0.0051(12) 0.0040(14) C2 0.0281(15) 0.0338(18) 0.0271(15) 0.0008(13) 0.0082(12) 0.0065(14) C1 0.0230(14) 0.0261(15) 0.0225(14) 0.0014(12) 0.0026(11) 0.0061(12) _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 O90 H90 1.15(7) . ? O90 H91 1.09(7) . ? O52 C67 1.212(4) . ? O51 C53 1.435(4) . ? O51 H51 0.82(4) . ? C68 C63 1.542(4) . ? C68 H68A 0.97(4) . ? C68 H68B 0.96(4) . ? C68 H68C 0.98(4) . ? C69 C60 1.536(4) . ? C69 H69A 0.97(5) . ? C69 H69B 0.97(4) . ? C69 H69C 0.95(4) . ? C67 C66 1.512(5) . ? C67 C63 1.522(4) . ? C66 C65 1.523(5) . ? C66 H66A 0.98(5) . ? C66 H66B 0.99(4) . ? C65 C64 1.535(4) . ? C65 H65A 0.97(4) . ? C65 H65B 0.96(4) . ? C64 C58 1.515(4) . ? C64 C63 1.542(4) . ? C64 H64A 0.98(3) . ? C63 C62 1.516(4) . ? C62 C61 1.535(4) . ? C62 H62A 0.99(4) . ? C62 H62B 0.95(3) . ? C61 C59 1.545(4) . ? C61 H61A 1.01(4) . ? C61 H61B 0.96(3) . ? C60 C51 1.544(4) . ? C60 C55 1.550(4) . ? C60 C59 1.551(4) . ? C59 C58 1.546(4) . ? C59 H59A 0.96(3) . ? C58 C57 1.529(5) . ? C58 H58A 1.02(4) . ? C57 C56 1.513(5) . ? C57 H57A 1.00(4) . ? C57 H57B 0.98(4) . ? C56 C55 1.529(4) . ? C56 H56A 0.99(4) . ? C56 H56B 0.98(5) . ? C55 C54 1.527(4) . ? C55 H55A 0.98(3) . ? C54 C53 1.516(5) . ? C54 H54A 0.97(3) . ? C54 H54B 0.97(4) . ? C53 C52 1.521(4) . ? C53 H53A 0.99(3) . ? C52 C51 1.533(4) . ? C52 H52A 1.00(3) . ? C52 H52B 1.01(4) . ? C51 H51A 1.03(3) . ? C51 H51B 0.95(4) . ? O2 C17 1.209(4) . ? O1 C3 1.433(4) . ? O1 H1 0.89(4) . ? C18 C13 1.546(4) . ? C18 H18A 0.97(4) . ? C18 H18B 0.91(4) . ? C18 H18C 1.02(3) . ? C19 C10 1.543(4) . ? C19 H19A 0.99(3) . ? C19 H19B 0.98(3) . ? C19 H19C 0.96(3) . ? C17 C16 1.517(4) . ? C17 C13 1.520(4) . ? C16 C15 1.535(4) . ? C16 H16A 0.94(4) . ? C16 H16B 0.98(4) . ? C15 C14 1.529(4) . ? C15 H15A 0.99(3) . ? C15 H15B 0.99(4) . ? C14 C8 1.520(4) . ? C14 C13 1.534(4) . ? C14 H14A 0.95(3) . ? C13 C12 1.522(4) . ? C12 C11 1.539(4) . ? C12 H12A 1.05(4) . ? C12 H12B 0.96(3) . ? C11 C9 1.541(4) . ? C11 H11A 0.97(3) . ? C11 H11B 0.98(3) . ? C10 C5 1.549(4) . ? C10 C9 1.550(4) . ? C10 C1 1.554(4) . ? C9 C8 1.550(4) . ? C9 H9A 0.99(3) . ? C8 C7 1.527(4) . ? C8 H8A 0.99(3) . ? C7 C6 1.524(4) . ? C7 H7A 0.98(4) . ? C7 H7B 0.97(3) . ? C6 C5 1.519(4) . ? C6 H6A 1.03(3) . ? C6 H6B 0.95(3) . ? C5 C4 1.528(4) . ? C5 H5A 0.98(3) . ? C4 C3 1.521(4) . ? C4 H4A 0.93(3) . ? C4 H4B 1.01(3) . ? C3 C2 1.519(4) . ? C3 H3A 0.97(3) . ? C2 C1 1.532(4) . ? C2 H2A 0.97(4) . ? C2 H2B 0.97(3) . ? C1 H1A 0.97(3) . ? C1 H1B 1.03(3) . ? 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 H90 O90 H91 100(4) . . ? C53 O51 H51 108(3) . . ? C63 C68 H68A 110(2) . . ? C63 C68 H68B 111(2) . . ? H68A C68 H68B 113(3) . . ? C63 C68 H68C 109(2) . . ? H68A C68 H68C 108(3) . . ? H68B C68 H68C 106(3) . . ? C60 C69 H69A 109(3) . . ? C60 C69 H69B 111(2) . . ? H69A C69 H69B 108(3) . . ? C60 C69 H69C 112(3) . . ? H69A C69 H69C 106(3) . . ? H69B C69 H69C 110(3) . . ? O52 C67 C66 125.3(3) . . ? O52 C67 C63 126.1(3) . . ? C66 C67 C63 108.6(3) . . ? C67 C66 C65 106.2(3) . . ? C67 C66 H66A 107(2) . . ? C65 C66 H66A 115(2) . . ? C67 C66 H66B 111(2) . . ? C65 C66 H66B 115(2) . . ? H66A C66 H66B 103(3) . . ? C66 C65 C64 102.6(3) . . ? C66 C65 H65A 110(2) . . ? C64 C65 H65A 111(2) . . ? C66 C65 H65B 113(2) . . ? C64 C65 H65B 109(2) . . ? H65A C65 H65B 111(3) . . ? C58 C64 C65 120.9(3) . . ? C58 C64 C63 113.0(3) . . ? C65 C64 C63 104.3(2) . . ? C58 C64 H64A 107.2(18) . . ? C65 C64 H64A 104.7(18) . . ? C63 C64 H64A 105.5(19) . . ? C62 C63 C67 117.3(3) . . ? C62 C63 C68 111.2(3) . . ? C67 C63 C68 104.7(3) . . ? C62 C63 C64 110.0(2) . . ? C67 C63 C64 99.2(2) . . ? C68 C63 C64 114.1(3) . . ? C63 C62 C61 110.5(3) . . ? C63 C62 H62A 109.3(19) . . ? C61 C62 H62A 109.3(18) . . ? C63 C62 H62B 109.5(18) . . ? C61 C62 H62B 112(2) . . ? H62A C62 H62B 106(3) . . ? C62 C61 C59 113.9(2) . . ? C62 C61 H61A 111(2) . . ? C59 C61 H61A 104.0(19) . . ? C62 C61 H61B 110.2(19) . . ? C59 C61 H61B 110(2) . . ? H61A C61 H61B 108(3) . . ? C69 C60 C51 108.6(2) . . ? C69 C60 C55 112.1(2) . . ? C51 C60 C55 107.0(2) . . ? C69 C60 C59 109.9(2) . . ? C51 C60 C59 110.6(2) . . ? C55 C60 C59 108.5(2) . . ? C61 C59 C58 111.1(2) . . ? C61 C59 C60 114.0(2) . . ? C58 C59 C60 112.9(2) . . ? C61 C59 H59A 104.0(18) . . ? C58 C59 H59A 107.2(18) . . ? C60 C59 H59A 106.9(18) . . ? C64 C58 C57 112.1(3) . . ? C64 C58 C59 108.3(2) . . ? C57 C58 C59 111.8(3) . . ? C64 C58 H58A 109.9(17) . . ? C57 C58 H58A 107.6(17) . . ? C59 C58 H58A 107.1(17) . . ? C56 C57 C58 112.3(3) . . ? C56 C57 H57A 110(2) . . ? C58 C57 H57A 106(2) . . ? C56 C57 H57B 110(2) . . ? C58 C57 H57B 109(2) . . ? H57A C57 H57B 109(3) . . ? C57 C56 C55 110.9(3) . . ? C57 C56 H56A 108(2) . . ? C55 C56 H56A 108(2) . . ? C57 C56 H56B 110(3) . . ? C55 C56 H56B 108(3) . . ? H56A C56 H56B 111(3) . . ? C54 C55 C56 111.9(2) . . ? C54 C55 C60 112.9(3) . . ? C56 C55 C60 111.9(2) . . ? C54 C55 H55A 108.9(17) . . ? C56 C55 H55A 105.4(17) . . ? C60 C55 H55A 105.3(17) . . ? C53 C54 C55 112.1(2) . . ? C53 C54 H54A 110.5(19) . . ? C55 C54 H54A 107.0(19) . . ? C53 C54 H54B 110(2) . . ? C55 C54 H54B 113(2) . . ? H54A C54 H54B 104(3) . . ? O51 C53 C54 106.4(3) . . ? O51 C53 C52 111.3(3) . . ? C54 C53 C52 111.3(3) . . ? O51 C53 H53A 108.2(19) . . ? C54 C53 H53A 110.3(18) . . ? C52 C53 H53A 109.3(18) . . ? C53 C52 C51 112.5(2) . . ? C53 C52 H52A 108(2) . . ? C51 C52 H52A 109.0(19) . . ? C53 C52 H52B 109(2) . . ? C51 C52 H52B 109(2) . . ? H52A C52 H52B 109(3) . . ? C52 C51 C60 113.0(2) . . ? C52 C51 H51A 109.2(15) . . ? C60 C51 H51A 110.8(15) . . ? C52 C51 H51B 110.3(18) . . ? C60 C51 H51B 110.3(19) . . ? H51A C51 H51B 103(2) . . ? C3 O1 H1 110(3) . . ? C13 C18 H18A 107(2) . . ? C13 C18 H18B 112(2) . . ? H18A C18 H18B 108(3) . . ? C13 C18 H18C 112.8(18) . . ? H18A C18 H18C 113(3) . . ? H18B C18 H18C 104(3) . . ? C10 C19 H19A 111(2) . . ? C10 C19 H19B 114.6(19) . . ? H19A C19 H19B 110(3) . . ? C10 C19 H19C 112(2) . . ? H19A C19 H19C 107(3) . . ? H19B C19 H19C 103(3) . . ? O2 C17 C16 124.3(3) . . ? O2 C17 C13 126.8(3) . . ? C16 C17 C13 108.9(2) . . ? C17 C16 C15 105.7(2) . . ? C17 C16 H16A 105(2) . . ? C15 C16 H16A 117(2) . . ? C17 C16 H16B 106(2) . . ? C15 C16 H16B 111(2) . . ? H16A C16 H16B 112(3) . . ? C14 C15 C16 101.8(2) . . ? C14 C15 H15A 113.7(17) . . ? C16 C15 H15A 111.5(18) . . ? C14 C15 H15B 114.1(18) . . ? C16 C15 H15B 109.3(19) . . ? H15A C15 H15B 106(3) . . ? C8 C14 C15 120.9(2) . . ? C8 C14 C13 113.7(2) . . ? C15 C14 C13 104.7(2) . . ? C8 C14 H14A 104.8(17) . . ? C15 C14 H14A 105.4(17) . . ? C13 C14 H14A 106.1(17) . . ? C17 C13 C12 117.4(2) . . ? C17 C13 C14 100.5(2) . . ? C12 C13 C14 109.3(2) . . ? C17 C13 C18 104.0(2) . . ? C12 C13 C18 111.3(2) . . ? C14 C13 C18 113.8(2) . . ? C13 C12 C11 110.2(2) . . ? C13 C12 H12A 111.9(19) . . ? C11 C12 H12A 108.4(19) . . ? C13 C12 H12B 108.5(19) . . ? C11 C12 H12B 112.6(18) . . ? H12A C12 H12B 105(3) . . ? C12 C11 C9 113.8(2) . . ? C12 C11 H11A 110.0(18) . . ? C9 C11 H11A 109.8(18) . . ? C12 C11 H11B 109(2) . . ? C9 C11 H11B 109.1(19) . . ? H11A C11 H11B 105(3) . . ? C19 C10 C5 112.5(2) . . ? C19 C10 C9 110.8(2) . . ? C5 C10 C9 107.6(2) . . ? C19 C10 C1 108.6(2) . . ? C5 C10 C1 107.2(2) . . ? C9 C10 C1 110.1(2) . . ? C11 C9 C10 114.8(2) . . ? C11 C9 C8 111.1(2) . . ? C10 C9 C8 112.8(2) . . ? C11 C9 H9A 107.7(16) . . ? C10 C9 H9A 104.7(17) . . ? C8 C9 H9A 105.0(16) . . ? C14 C8 C7 111.1(2) . . ? C14 C8 C9 107.6(2) . . ? C7 C8 C9 111.9(2) . . ? C14 C8 H8A 110.4(17) . . ? C7 C8 H8A 107.1(16) . . ? C9 C8 H8A 108.8(17) . . ? C6 C7 C8 112.1(2) . . ? C6 C7 H7A 108.6(18) . . ? C8 C7 H7A 107.9(18) . . ? C6 C7 H7B 109.1(16) . . ? C8 C7 H7B 110.5(16) . . ? H7A C7 H7B 109(2) . . ? C5 C6 C7 110.8(2) . . ? C5 C6 H6A 111.4(16) . . ? C7 C6 H6A 110.4(16) . . ? C5 C6 H6B 110(2) . . ? C7 C6 H6B 108(2) . . ? H6A C6 H6B 105(3) . . ? C6 C5 C4 112.1(2) . . ? C6 C5 C10 112.4(2) . . ? C4 C5 C10 112.9(2) . . ? C6 C5 H5A 108.3(17) . . ? C4 C5 H5A 106.4(16) . . ? C10 C5 H5A 104.0(16) . . ? C3 C4 C5 111.5(2) . . ? C3 C4 H4A 107.8(19) . . ? C5 C4 H4A 108.3(18) . . ? C3 C4 H4B 111.9(19) . . ? C5 C4 H4B 106.7(18) . . ? H4A C4 H4B 110(3) . . ? O1 C3 C2 111.1(3) . . ? O1 C3 C4 106.9(3) . . ? C2 C3 C4 110.3(3) . . ? O1 C3 H3A 108.3(18) . . ? C2 C3 H3A 112.6(16) . . ? C4 C3 H3A 107.3(18) . . ? C3 C2 C1 112.4(2) . . ? C3 C2 H2A 111(2) . . ? C1 C2 H2A 108(2) . . ? C3 C2 H2B 108.5(19) . . ? C1 C2 H2B 110.6(19) . . ? H2A C2 H2B 106(3) . . ? C2 C1 C10 113.5(2) . . ? C2 C1 H1A 108.2(16) . . ? C10 C1 H1A 109.6(17) . . ? C2 C1 H1B 111.1(16) . . ? C10 C1 H1B 105.9(16) . . ? H1A C1 H1B 108(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O52 C67 C66 C65 -170.9(3) . . . . ? C63 C67 C66 C65 7.7(4) . . . . ? C67 C66 C65 C64 19.4(4) . . . . ? C66 C65 C64 C58 -168.0(3) . . . . ? C66 C65 C64 C63 -39.6(3) . . . . ? O52 C67 C63 C62 29.4(5) . . . . ? C66 C67 C63 C62 -149.2(3) . . . . ? O52 C67 C63 C68 -94.4(4) . . . . ? C66 C67 C63 C68 87.0(3) . . . . ? O52 C67 C63 C64 147.6(3) . . . . ? C66 C67 C63 C64 -31.0(3) . . . . ? C58 C64 C63 C62 -60.3(3) . . . . ? C65 C64 C63 C62 166.6(3) . . . . ? C58 C64 C63 C67 176.2(2) . . . . ? C65 C64 C63 C67 43.1(3) . . . . ? C58 C64 C63 C68 65.5(3) . . . . ? C65 C64 C63 C68 -67.6(3) . . . . ? C67 C63 C62 C61 166.3(3) . . . . ? C68 C63 C62 C61 -73.3(3) . . . . ? C64 C63 C62 C61 54.1(3) . . . . ? C63 C62 C61 C59 -52.6(4) . . . . ? C62 C61 C59 C58 53.0(3) . . . . ? C62 C61 C59 C60 -178.1(3) . . . . ? C69 C60 C59 C61 -58.8(3) . . . . ? C51 C60 C59 C61 61.2(3) . . . . ? C55 C60 C59 C61 178.2(2) . . . . ? C69 C60 C59 C58 69.3(3) . . . . ? C51 C60 C59 C58 -170.8(2) . . . . ? C55 C60 C59 C58 -53.7(3) . . . . ? C65 C64 C58 C57 -52.4(4) . . . . ? C63 C64 C58 C57 -176.9(3) . . . . ? C65 C64 C58 C59 -176.2(3) . . . . ? C63 C64 C58 C59 59.4(3) . . . . ? C61 C59 C58 C64 -54.4(3) . . . . ? C60 C59 C58 C64 176.1(2) . . . . ? C61 C59 C58 C57 -178.3(3) . . . . ? C60 C59 C58 C57 52.2(3) . . . . ? C64 C58 C57 C56 -174.0(3) . . . . ? C59 C58 C57 C56 -52.3(4) . . . . ? C58 C57 C56 C55 55.5(4) . . . . ? C57 C56 C55 C54 173.5(3) . . . . ? C57 C56 C55 C60 -58.7(4) . . . . ? C69 C60 C55 C54 62.5(3) . . . . ? C51 C60 C55 C54 -56.5(3) . . . . ? C59 C60 C55 C54 -175.8(2) . . . . ? C69 C60 C55 C56 -64.7(3) . . . . ? C51 C60 C55 C56 176.3(3) . . . . ? C59 C60 C55 C56 56.9(3) . . . . ? C56 C55 C54 C53 -175.8(3) . . . . ? C60 C55 C54 C53 56.9(4) . . . . ? C55 C54 C53 O51 68.9(3) . . . . ? C55 C54 C53 C52 -52.6(4) . . . . ? O51 C53 C52 C51 -66.8(3) . . . . ? C54 C53 C52 C51 51.8(3) . . . . ? C53 C52 C51 C60 -55.2(3) . . . . ? C69 C60 C51 C52 -65.8(3) . . . . ? C55 C60 C51 C52 55.5(3) . . . . ? C59 C60 C51 C52 173.5(2) . . . . ? O2 C17 C16 C15 179.7(3) . . . . ? C13 C17 C16 C15 0.1(3) . . . . ? C17 C16 C15 C14 25.0(3) . . . . ? C16 C15 C14 C8 -171.4(3) . . . . ? C16 C15 C14 C13 -41.5(3) . . . . ? O2 C17 C13 C12 37.1(4) . . . . ? C16 C17 C13 C12 -143.3(3) . . . . ? O2 C17 C13 C14 155.5(3) . . . . ? C16 C17 C13 C14 -24.9(3) . . . . ? O2 C17 C13 C18 -86.5(4) . . . . ? C16 C17 C13 C18 93.1(3) . . . . ? C8 C14 C13 C17 175.0(2) . . . . ? C15 C14 C13 C17 40.9(3) . . . . ? C8 C14 C13 C12 -60.8(3) . . . . ? C15 C14 C13 C12 165.1(2) . . . . ? C8 C14 C13 C18 64.5(3) . . . . ? C15 C14 C13 C18 -69.6(3) . . . . ? C17 C13 C12 C11 168.1(2) . . . . ? C14 C13 C12 C11 54.5(3) . . . . ? C18 C13 C12 C11 -72.2(3) . . . . ? C13 C12 C11 C9 -53.5(3) . . . . ? C12 C11 C9 C10 -176.9(2) . . . . ? C12 C11 C9 C8 53.7(3) . . . . ? C19 C10 C9 C11 -60.1(3) . . . . ? C5 C10 C9 C11 176.5(2) . . . . ? C1 C10 C9 C11 60.1(3) . . . . ? C19 C10 C9 C8 68.4(3) . . . . ? C5 C10 C9 C8 -54.9(3) . . . . ? C1 C10 C9 C8 -171.4(2) . . . . ? C15 C14 C8 C7 -51.7(4) . . . . ? C13 C14 C8 C7 -177.6(2) . . . . ? C15 C14 C8 C9 -174.5(2) . . . . ? C13 C14 C8 C9 59.6(3) . . . . ? C11 C9 C8 C14 -54.2(3) . . . . ? C10 C9 C8 C14 175.3(2) . . . . ? C11 C9 C8 C7 -176.5(2) . . . . ? C10 C9 C8 C7 53.0(3) . . . . ? C14 C8 C7 C6 -171.8(3) . . . . ? C9 C8 C7 C6 -51.5(3) . . . . ? C8 C7 C6 C5 54.4(3) . . . . ? C7 C6 C5 C4 172.4(2) . . . . ? C7 C6 C5 C10 -59.1(3) . . . . ? C19 C10 C5 C6 -63.9(3) . . . . ? C9 C10 C5 C6 58.4(3) . . . . ? C1 C10 C5 C6 176.7(2) . . . . ? C19 C10 C5 C4 64.2(3) . . . . ? C9 C10 C5 C4 -173.5(2) . . . . ? C1 C10 C5 C4 -55.2(3) . . . . ? C6 C5 C4 C3 -173.5(3) . . . . ? C10 C5 C4 C3 58.3(3) . . . . ? C5 C4 C3 O1 65.5(3) . . . . ? C5 C4 C3 C2 -55.5(3) . . . . ? O1 C3 C2 C1 -64.5(3) . . . . ? C4 C3 C2 C1 53.9(4) . . . . ? C3 C2 C1 C10 -54.9(4) . . . . ? C19 C10 C1 C2 -68.4(3) . . . . ? C5 C10 C1 C2 53.4(3) . . . . ? C9 C10 C1 C2 170.1(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O51 H51 O2 0.82(4) 1.94(4) 2.756(3) 179(4) 1_565 O1 H1 O90 0.89(4) 1.95(4) 2.831(3) 169(3) 1_544 O90 H91 O52 1.09(7) 1.70(7) 2.747(4) 158(5) . O90 H90 O51 1.15(7) 1.66(7) 2.800(3) 169(5) 2_646 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.334 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.045 # Attachment 'STR0316.CIF' data_str0316 _database_code_depnum_ccdc_archive 'CCDC 293345' _iucr_compatibility_tag ACTA95 _vrf_DIFF020_str0316 ; PROBLEM: _diffrn_standards_interval_count and RESPONSE: Area detector used ; _vrf_PLAT035_str0316 ; PROBLEM: No _chemical_absolute_configuration info given . RESPONSE: Light atom structure - Flack parameter meaningless, consequently the absolute configuration cannot be deduced. ; # end Validation Reply Form #============================================================================ # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_acknowledgements ; ? ; _publ_section_figure_captions ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_references ; Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (1996). SADABS. University of G\"ottingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of G\"ottingen, Germany. ; _publ_section_exptl_refinement ; All H atoms were located in a difference map and were refined isotropically. ; #========================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; Androsterone ; _chemical_name_common Androsterone _chemical_melting_point ? _chemical_formula_moiety 'C19 H30 O2' _chemical_formula_sum 'C19 H30 O2' _chemical_formula_weight 290.43 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 _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.4045(9) _cell_length_b 7.9586(8) _cell_length_c 11.6746(12) _cell_angle_alpha 90.00 _cell_angle_beta 111.274(2) _cell_angle_gamma 90.00 _cell_volume 814.26(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2766 _cell_measurement_theta_min 2.324 _cell_measurement_theta_max 27.770 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9613 _exptl_absorpt_correction_T_max 0.9922 _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 7158 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2069 _reflns_number_gt 1957 _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^)+(0.0658P)^2^+0.1371P] 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_abs_structure_details #'Flack H D (1983), Acta Cryst. A39, 876-881' #_refine_ls_abs_structure_Flack 0.9(16) _refine_ls_number_reflns 2069 _refine_ls_number_parameters 310 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _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 O2 O 0.19431(18) 0.2269(3) 0.04948(14) 0.0372(4) Uani 1 1 d . . . O1 O 0.6506(2) 0.3973(3) 0.89653(16) 0.0406(4) Uani 1 1 d . . . H1 H 0.691(3) 0.491(5) 0.914(3) 0.042(8) Uiso 1 1 d . . . C18 C -0.0356(2) 0.3131(4) 0.1979(2) 0.0348(5) Uani 1 1 d . . . H18C H -0.073(4) 0.207(5) 0.169(3) 0.058(9) Uiso 1 1 d . . . H18B H -0.062(3) 0.340(4) 0.269(3) 0.045(7) Uiso 1 1 d . . . H18A H -0.088(3) 0.386(5) 0.130(3) 0.053(9) Uiso 1 1 d . . . C19 C 0.1300(2) 0.3554(3) 0.6413(2) 0.0304(4) Uani 1 1 d . . . H19C H 0.134(3) 0.378(4) 0.722(3) 0.045(8) Uiso 1 1 d . . . H19B H 0.056(3) 0.439(4) 0.583(3) 0.044(8) Uiso 1 1 d . . . H19A H 0.087(3) 0.251(4) 0.621(3) 0.043(8) Uiso 1 1 d . . . C16 C 0.1473(3) 0.5217(4) 0.0765(2) 0.0361(5) Uani 1 1 d . . . H16B H 0.053(3) 0.536(4) 0.007(3) 0.040(8) Uiso 1 1 d . . . H16A H 0.238(3) 0.546(4) 0.053(3) 0.038(7) Uiso 1 1 d . . . C15 C 0.1497(3) 0.6128(3) 0.1938(2) 0.0343(5) Uani 1 1 d . . . H15B H 0.050(3) 0.647(4) 0.191(2) 0.034(7) Uiso 1 1 d . . . H15A H 0.211(4) 0.712(5) 0.206(3) 0.056(9) Uiso 1 1 d . . . C2 C 0.4249(3) 0.2369(3) 0.8513(2) 0.0356(5) Uani 1 1 d . . . H2B H 0.498(3) 0.148(4) 0.892(2) 0.032(7) Uiso 1 1 d . . . H2A H 0.328(3) 0.224(4) 0.868(3) 0.038(7) Uiso 1 1 d . . . C17 C 0.1627(2) 0.3360(3) 0.10830(18) 0.0281(4) Uani 1 1 d . . . C7 C 0.2870(2) 0.6634(2) 0.4802(2) 0.0260(4) Uani 1 1 d . . . H7B H 0.386(3) 0.661(3) 0.4755(19) 0.013(5) Uiso 1 1 d . . . H7A H 0.237(3) 0.764(4) 0.433(2) 0.035(7) Uiso 1 1 d . . . C1 C 0.3883(3) 0.2163(3) 0.71297(18) 0.0265(4) Uani 1 1 d . . . H1B H 0.337(3) 0.115(3) 0.683(2) 0.017(5) Uiso 1 1 d . . . H1A H 0.485(3) 0.214(4) 0.697(2) 0.026(6) Uiso 1 1 d . . . C12 C 0.2161(3) 0.1644(3) 0.30696(19) 0.0310(5) Uani 1 1 d . . . H12B H 0.169(3) 0.062(4) 0.270(3) 0.039(8) Uiso 1 1 d . . . H12A H 0.328(3) 0.160(4) 0.312(2) 0.034(7) Uiso 1 1 d . . . C13 C 0.1391(2) 0.3145(3) 0.22979(18) 0.0241(4) Uani 1 1 d . . . C3 C 0.5006(3) 0.4022(3) 0.90065(19) 0.0345(5) Uani 1 1 d . . . H3A H 0.516(3) 0.417(4) 0.985(3) 0.034(7) Uiso 1 1 d . . . C11 C 0.2121(3) 0.1808(3) 0.43706(19) 0.0285(5) Uani 1 1 d . . . H11B H 0.102(3) 0.174(4) 0.435(2) 0.032(7) Uiso 1 1 d . . . H11A H 0.260(3) 0.089(4) 0.482(3) 0.032(7) Uiso 1 1 d . . . C5 C 0.3762(2) 0.5262(3) 0.68835(18) 0.0219(4) Uani 1 1 d . . . H5A H 0.472(3) 0.518(3) 0.682(2) 0.016(5) Uiso 1 1 d . . . C6 C 0.2990(3) 0.6805(3) 0.6132(2) 0.0274(4) Uani 1 1 d . . . H6B H 0.199(3) 0.695(3) 0.619(2) 0.024(6) Uiso 1 1 d . . . H6A H 0.351(3) 0.782(4) 0.653(2) 0.031(7) Uiso 1 1 d . . . C4 C 0.4083(3) 0.5486(3) 0.8257(2) 0.0294(5) Uani 1 1 d . . . H4B H 0.311(3) 0.558(4) 0.838(2) 0.033(7) Uiso 1 1 d . . . H4A H 0.461(3) 0.653(4) 0.852(3) 0.037(7) Uiso 1 1 d . . . C14 C 0.2146(2) 0.4782(2) 0.29331(18) 0.0226(4) Uani 1 1 d . . . H14A H 0.321(3) 0.469(3) 0.306(2) 0.016(5) Uiso 1 1 d . . . C9 C 0.2835(2) 0.3459(2) 0.50046(17) 0.0188(3) Uani 1 1 d . . . H9A H 0.388(2) 0.345(3) 0.5080(18) 0.016(5) Uiso 1 1 d . . . C10 C 0.2909(2) 0.3611(2) 0.63525(17) 0.0209(4) Uani 1 1 d . . . C8 C 0.2083(2) 0.5006(2) 0.42103(18) 0.0204(4) Uani 1 1 d . . . H8A H 0.104(3) 0.511(3) 0.413(2) 0.021(5) 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 O2 0.0379(8) 0.0489(10) 0.0277(7) -0.0031(7) 0.0155(6) 0.0027(8) O1 0.0383(9) 0.0376(10) 0.0358(9) -0.0056(7) 0.0012(7) 0.0089(8) C18 0.0236(9) 0.0534(15) 0.0280(10) -0.0049(11) 0.0100(8) -0.0098(10) C19 0.0289(10) 0.0320(12) 0.0363(11) -0.0020(9) 0.0190(9) -0.0049(9) C16 0.0379(11) 0.0439(13) 0.0279(11) 0.0101(10) 0.0137(9) 0.0029(10) C15 0.0421(13) 0.0304(12) 0.0307(11) 0.0102(9) 0.0135(10) 0.0041(10) C2 0.0545(14) 0.0304(12) 0.0224(10) 0.0047(9) 0.0146(10) 0.0059(11) C17 0.0201(8) 0.0412(12) 0.0222(9) 0.0014(9) 0.0066(7) -0.0007(8) C7 0.0315(11) 0.0155(9) 0.0301(10) 0.0028(8) 0.0102(8) -0.0008(7) C1 0.0375(11) 0.0187(9) 0.0236(9) 0.0005(8) 0.0113(8) 0.0014(8) C12 0.0462(13) 0.0210(10) 0.0248(10) -0.0033(8) 0.0117(9) 0.0004(9) C13 0.0237(8) 0.0269(11) 0.0227(9) -0.0001(8) 0.0096(7) -0.0029(8) C3 0.0482(13) 0.0337(12) 0.0197(10) -0.0028(9) 0.0101(9) 0.0073(10) C11 0.0424(13) 0.0189(10) 0.0237(10) -0.0002(8) 0.0112(9) -0.0035(8) C5 0.0221(8) 0.0194(9) 0.0245(9) -0.0031(7) 0.0087(7) 0.0018(7) C6 0.0330(11) 0.0165(9) 0.0326(11) -0.0027(8) 0.0117(9) 0.0010(8) C4 0.0350(11) 0.0260(11) 0.0270(10) -0.0055(8) 0.0109(8) 0.0047(9) C14 0.0200(8) 0.0223(10) 0.0262(10) 0.0038(8) 0.0092(7) 0.0000(7) C9 0.0207(8) 0.0149(8) 0.0217(8) 0.0007(7) 0.0087(6) 0.0003(7) C10 0.0232(8) 0.0189(9) 0.0230(8) -0.0003(7) 0.0110(7) 0.0005(7) C8 0.0185(8) 0.0178(9) 0.0254(9) 0.0031(7) 0.0085(7) 0.0003(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O2 C17 1.209(3) . ? O1 C3 1.430(3) . ? O1 H1 0.83(4) . ? C18 C13 1.547(3) . ? C18 H18C 0.93(4) . ? C18 H18B 0.97(3) . ? C18 H18A 0.96(4) . ? C19 C10 1.541(3) . ? C19 H19C 0.94(3) . ? C19 H19B 1.02(3) . ? C19 H19A 0.92(3) . ? C16 C17 1.518(4) . ? C16 C15 1.543(4) . ? C16 H16B 0.97(3) . ? C16 H16A 1.00(3) . ? C15 C14 1.535(3) . ? C15 H15B 0.96(3) . ? C15 H15A 0.96(4) . ? C2 C3 1.507(4) . ? C2 C1 1.533(3) . ? C2 H2B 0.98(3) . ? C2 H2A 1.00(3) . ? C17 C13 1.523(3) . ? C7 C6 1.521(3) . ? C7 C8 1.527(3) . ? C7 H7B 0.95(2) . ? C7 H7A 0.99(3) . ? C1 C10 1.545(3) . ? C1 H1B 0.94(3) . ? C1 H1A 0.99(3) . ? C12 C13 1.514(3) . ? C12 C11 1.539(3) . ? C12 H12B 0.96(3) . ? C12 H12A 1.03(3) . ? C13 C14 1.539(3) . ? C3 C4 1.525(3) . ? C3 H3A 0.95(3) . ? C11 C9 1.538(3) . ? C11 H11B 1.02(3) . ? C11 H11A 0.92(3) . ? C5 C4 1.530(3) . ? C5 C6 1.531(3) . ? C5 C10 1.548(3) . ? C5 H5A 0.94(2) . ? C6 H6B 0.97(2) . ? C6 H6A 0.97(3) . ? C4 H4B 0.99(3) . ? C4 H4A 0.96(3) . ? C14 C8 1.524(3) . ? C14 H14A 0.96(2) . ? C9 C8 1.549(2) . ? C9 C10 1.554(2) . ? C9 H9A 0.95(2) . ? C8 H8A 0.95(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 H1 110(2) . . ? C13 C18 H18C 109(2) . . ? C13 C18 H18B 111.7(17) . . ? H18C C18 H18B 109(3) . . ? C13 C18 H18A 112.4(18) . . ? H18C C18 H18A 104(3) . . ? H18B C18 H18A 111(3) . . ? C10 C19 H19C 110.6(17) . . ? C10 C19 H19B 112.9(16) . . ? H19C C19 H19B 108(3) . . ? C10 C19 H19A 111.0(19) . . ? H19C C19 H19A 107(3) . . ? H19B C19 H19A 107(3) . . ? C17 C16 C15 105.72(18) . . ? C17 C16 H16B 107(2) . . ? C15 C16 H16B 113.9(17) . . ? C17 C16 H16A 103.6(18) . . ? C15 C16 H16A 114.3(17) . . ? H16B C16 H16A 111(2) . . ? C14 C15 C16 102.57(19) . . ? C14 C15 H15B 110.0(16) . . ? C16 C15 H15B 113.6(16) . . ? C14 C15 H15A 114(2) . . ? C16 C15 H15A 110(2) . . ? H15B C15 H15A 107(3) . . ? C3 C2 C1 112.98(19) . . ? C3 C2 H2B 106.8(17) . . ? C1 C2 H2B 106.6(15) . . ? C3 C2 H2A 110.6(18) . . ? C1 C2 H2A 108.7(16) . . ? H2B C2 H2A 111(2) . . ? O2 C17 C16 125.6(2) . . ? O2 C17 C13 126.7(2) . . ? C16 C17 C13 107.72(18) . . ? C6 C7 C8 112.45(16) . . ? C6 C7 H7B 110.4(12) . . ? C8 C7 H7B 106.4(13) . . ? C6 C7 H7A 110.0(16) . . ? C8 C7 H7A 112.3(16) . . ? H7B C7 H7A 105(2) . . ? C2 C1 C10 113.44(17) . . ? C2 C1 H1B 111.7(14) . . ? C10 C1 H1B 107.8(15) . . ? C2 C1 H1A 109.3(14) . . ? C10 C1 H1A 107.1(15) . . ? H1B C1 H1A 107(2) . . ? C13 C12 C11 110.03(18) . . ? C13 C12 H12B 111.3(18) . . ? C11 C12 H12B 110.3(17) . . ? C13 C12 H12A 108.6(16) . . ? C11 C12 H12A 109.5(15) . . ? H12B C12 H12A 107(2) . . ? C12 C13 C17 116.30(18) . . ? C12 C13 C14 110.12(15) . . ? C17 C13 C14 98.96(16) . . ? C12 C13 C18 112.01(19) . . ? C17 C13 C18 106.11(17) . . ? C14 C13 C18 112.72(17) . . ? O1 C3 C2 107.35(19) . . ? O1 C3 C4 111.4(2) . . ? C2 C3 C4 110.88(19) . . ? O1 C3 H3A 105.0(16) . . ? C2 C3 H3A 112.2(18) . . ? C4 C3 H3A 109.9(17) . . ? C9 C11 C12 112.60(17) . . ? C9 C11 H11B 108.3(16) . . ? C12 C11 H11B 110.9(14) . . ? C9 C11 H11A 111.5(18) . . ? C12 C11 H11A 108.6(17) . . ? H11B C11 H11A 105(2) . . ? C4 C5 C6 112.30(17) . . ? C4 C5 C10 113.27(17) . . ? C6 C5 C10 112.48(15) . . ? C4 C5 H5A 105.5(13) . . ? C6 C5 H5A 106.3(15) . . ? C10 C5 H5A 106.3(15) . . ? C7 C6 C5 110.91(16) . . ? C7 C6 H6B 111.3(14) . . ? C5 C6 H6B 109.0(15) . . ? C7 C6 H6A 113.9(16) . . ? C5 C6 H6A 109.7(16) . . ? H6B C6 H6A 102(2) . . ? C3 C4 C5 111.53(17) . . ? C3 C4 H4B 109.8(17) . . ? C5 C4 H4B 109.0(16) . . ? C3 C4 H4A 111.1(17) . . ? C5 C4 H4A 108.5(16) . . ? H4B C4 H4A 107(2) . . ? C8 C14 C15 120.87(17) . . ? C8 C14 C13 113.28(15) . . ? C15 C14 C13 103.81(17) . . ? C8 C14 H14A 105.6(13) . . ? C15 C14 H14A 106.0(13) . . ? C13 C14 H14A 106.2(14) . . ? C11 C9 C8 111.48(14) . . ? C11 C9 C10 113.88(14) . . ? C8 C9 C10 112.78(14) . . ? C11 C9 H9A 107.1(14) . . ? C8 C9 H9A 106.9(14) . . ? C10 C9 H9A 103.9(12) . . ? C19 C10 C1 109.49(17) . . ? C19 C10 C5 112.44(16) . . ? C1 C10 C5 106.72(15) . . ? C19 C10 C9 111.11(15) . . ? C1 C10 C9 109.63(15) . . ? C5 C10 C9 107.33(15) . . ? C14 C8 C7 110.91(16) . . ? C14 C8 C9 108.75(15) . . ? C7 C8 C9 111.24(15) . . ? C14 C8 H8A 108.6(14) . . ? C7 C8 H8A 106.4(16) . . ? C9 C8 H8A 111.0(16) . . ? 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 C17 C16 C15 C14 16.6(2) . . . . ? C15 C16 C17 O2 -165.1(2) . . . . ? C15 C16 C17 C13 12.1(2) . . . . ? C3 C2 C1 C10 -55.0(3) . . . . ? C11 C12 C13 C17 167.52(18) . . . . ? C11 C12 C13 C14 56.0(2) . . . . ? C11 C12 C13 C18 -70.2(2) . . . . ? O2 C17 C13 C12 24.0(3) . . . . ? C16 C17 C13 C12 -153.19(19) . . . . ? O2 C17 C13 C14 141.8(2) . . . . ? C16 C17 C13 C14 -35.39(19) . . . . ? O2 C17 C13 C18 -101.3(2) . . . . ? C16 C17 C13 C18 81.5(2) . . . . ? C1 C2 C3 O1 -69.5(2) . . . . ? C1 C2 C3 C4 52.3(3) . . . . ? C13 C12 C11 C9 -55.7(2) . . . . ? C8 C7 C6 C5 54.1(2) . . . . ? C4 C5 C6 C7 172.81(17) . . . . ? C10 C5 C6 C7 -58.0(2) . . . . ? O1 C3 C4 C5 66.1(2) . . . . ? C2 C3 C4 C5 -53.3(2) . . . . ? C6 C5 C4 C3 -173.79(19) . . . . ? C10 C5 C4 C3 57.4(2) . . . . ? C16 C15 C14 C8 -167.74(17) . . . . ? C16 C15 C14 C13 -39.3(2) . . . . ? C12 C13 C14 C8 -58.87(19) . . . . ? C17 C13 C14 C8 178.75(15) . . . . ? C18 C13 C14 C8 67.0(2) . . . . ? C12 C13 C14 C15 168.21(18) . . . . ? C17 C13 C14 C15 45.83(18) . . . . ? C18 C13 C14 C15 -65.9(2) . . . . ? C12 C11 C9 C8 54.8(2) . . . . ? C12 C11 C9 C10 -176.17(17) . . . . ? C2 C1 C10 C19 -67.7(2) . . . . ? C2 C1 C10 C5 54.3(2) . . . . ? C2 C1 C10 C9 170.21(18) . . . . ? C4 C5 C10 C19 64.0(2) . . . . ? C6 C5 C10 C19 -64.6(2) . . . . ? C4 C5 C10 C1 -56.03(19) . . . . ? C6 C5 C10 C1 175.30(17) . . . . ? C4 C5 C10 C9 -173.49(15) . . . . ? C6 C5 C10 C9 57.84(19) . . . . ? C11 C9 C10 C19 -61.0(2) . . . . ? C8 C9 C10 C19 67.3(2) . . . . ? C11 C9 C10 C1 60.2(2) . . . . ? C8 C9 C10 C1 -171.50(15) . . . . ? C11 C9 C10 C5 175.72(16) . . . . ? C8 C9 C10 C5 -55.95(18) . . . . ? C15 C14 C8 C7 -56.9(2) . . . . ? C13 C14 C8 C7 179.10(15) . . . . ? C15 C14 C8 C9 -179.49(18) . . . . ? C13 C14 C8 C9 56.46(18) . . . . ? C6 C7 C8 C14 -173.51(16) . . . . ? C6 C7 C8 C9 -52.3(2) . . . . ? C11 C9 C8 C14 -53.60(18) . . . . ? C10 C9 C8 C14 176.83(14) . . . . ? C11 C9 C8 C7 -176.05(17) . . . . ? C10 C9 C8 C7 54.38(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.83(4) 2.13(4) 2.956(3) 175(3) 2_656 _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.349 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.042