Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Gerardo Burton' _publ_contact_author_address ; Universidad de Buenos Aires Buenos Aires C1428EGA ARGENTINA ; _publ_contact_author_email BURTON@QO.FCEN.UBA.AR _publ_section_title ; Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones ; loop_ _publ_author_name 'Gerardo Burton' 'Ricardo F. Baggio' 'Nora R. Ceballos' 'Pablo H. Di Chenna' 'M Teresa Garland' ; J.M.Sonego ; 'Adriana S. Veleiro' data_ExTwin _database_code_depnum_ccdc_archive 'CCDC 622907' _vrf_PLAT035_ExTwin ; PROBLEM: No _chemical_absolute_configuration info given . ? RESPONSE: This is an organic structure measured with Molybdenum Kalpha radiation,and no meaningful Friedel differences are to be expected. For that reason the data were merged. ; # end Validation Reply Form _audit_update_record ; 2007-05-08 # Formatted by publCIF ; # Recrystallized fron dioxane _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,19-cyclopregn-4-ene-3,20-dione ; _chemical_name_common 6,19-cyclopregn-4-ene-3,20-dione _chemical_melting_point ? _chemical_formula_moiety 'C21 H28 O2' _chemical_formula_sum 'C21 H28 O2' _chemical_formula_weight 312.43 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_Hall ' P 2yb ' _symmetry_space_group_name_H-M ' P 21 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.3312(12) _cell_length_b 11.4371(12) _cell_length_c 14.5628(16) _cell_angle_alpha 90.00 _cell_angle_beta 111.863(2) _cell_angle_gamma 90.00 _cell_volume 1751.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.185 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 298(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 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13024 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0599 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 28.14 _reflns_number_total 4172 _reflns_number_gt 2950 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART-NT (Bruker, 2001)' _computing_cell_refinement 'SAINT-NT (Bruker, 2001 )' _computing_data_reduction 'SAINT-NT (Bruker, 2001 )' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT (Bruker, 2001)' _computing_publication_material 'SHELXTL-NT (Bruker, 2001), PLATON (Spek, 2005)' _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^)+(0.0230P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Friedel pairs merged ' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 4172 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0570 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.007 _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 O1A O 0.2050(3) -0.1337(2) -0.07450(18) 0.0953(9) Uani 1 1 d . . . O2A O 0.0904(4) 0.7431(3) 0.1730(3) 0.1554(15) Uani 1 1 d . . . C1A C 0.4228(3) 0.0763(3) 0.0890(2) 0.0718(11) Uani 1 1 d . . . H1A1 H 0.4471 0.0988 0.1578 0.086 Uiso 1 1 calc R . . H1A2 H 0.4957 0.0400 0.0808 0.086 Uiso 1 1 calc R . . C2A C 0.3126(3) -0.0096(3) 0.0607(2) 0.0719(10) Uani 1 1 d . . . H2A1 H 0.3412 -0.0805 0.0992 0.086 Uiso 1 1 calc R . . H2A2 H 0.2454 0.0239 0.0785 0.086 Uiso 1 1 calc R . . C3A C 0.2584(3) -0.0417(3) -0.0470(3) 0.0640(10) Uani 1 1 d . . . C4A C 0.2708(3) 0.0448(3) -0.1166(2) 0.0651(9) Uani 1 1 d . . . H4A H 0.2435 0.0281 -0.1838 0.078 Uiso 1 1 calc R . . C5A C 0.3215(3) 0.1471(3) -0.0823(2) 0.0554(8) Uani 1 1 d . . . C6A C 0.3658(3) 0.2565(4) -0.1144(3) 0.0709(10) Uani 1 1 d . . . H6A H 0.3895 0.2492 -0.1723 0.085 Uiso 1 1 calc R . . C7A C 0.2735(3) 0.3558(3) -0.1185(2) 0.0633(9) Uani 1 1 d . . . H7A1 H 0.1875 0.3331 -0.1596 0.076 Uiso 1 1 calc R . . H7A2 H 0.2956 0.4250 -0.1471 0.076 Uiso 1 1 calc R . . C8A C 0.2812(3) 0.3826(3) -0.0128(2) 0.0473(7) Uani 1 1 d . . . H8A H 0.3604 0.4261 0.0197 0.057 Uiso 1 1 calc R . . C9A C 0.2931(3) 0.2695(3) 0.0461(2) 0.0468(7) Uani 1 1 d . . . H9A H 0.2086 0.2332 0.0215 0.056 Uiso 1 1 calc R . . C10A C 0.3830(3) 0.1827(3) 0.0240(2) 0.0559(8) Uani 1 1 d . . . C11A C 0.3233(3) 0.2985(3) 0.1550(2) 0.0594(9) Uani 1 1 d . . . H11A H 0.3263 0.2268 0.1914 0.071 Uiso 1 1 calc R . . H11B H 0.4063 0.3353 0.1826 0.071 Uiso 1 1 calc R . . C12A C 0.2235(3) 0.3802(3) 0.1671(2) 0.0563(8) Uani 1 1 d . . . H12A H 0.1433 0.3387 0.1482 0.068 Uiso 1 1 calc R . . H12B H 0.2493 0.4015 0.2362 0.068 Uiso 1 1 calc R . . C13A C 0.2037(2) 0.4910(3) 0.1054(2) 0.0492(8) Uani 1 1 d . . . C14A C 0.1761(3) 0.4554(3) -0.0024(2) 0.0492(8) Uani 1 1 d . . . H14A H 0.1010 0.4047 -0.0219 0.059 Uiso 1 1 calc R . . C15A C 0.1332(3) 0.5678(3) -0.0604(2) 0.0697(10) Uani 1 1 d . . . H15A H 0.0802 0.5517 -0.1288 0.084 Uiso 1 1 calc R . . H15B H 0.2056 0.6144 -0.0587 0.084 Uiso 1 1 calc R . . C16A C 0.0571(3) 0.6305(3) -0.0070(3) 0.0824(11) Uani 1 1 d . . . H16A H 0.0847 0.7111 0.0068 0.099 Uiso 1 1 calc R . . H16B H -0.0330 0.6298 -0.0475 0.099 Uiso 1 1 calc R . . C17A C 0.0823(3) 0.5636(3) 0.0897(3) 0.0634(9) Uani 1 1 d . . . H17A H 0.0121 0.5082 0.0776 0.076 Uiso 1 1 calc R . . C18A C 0.3198(3) 0.5712(3) 0.1481(2) 0.0659(10) Uani 1 1 d . . . H18A H 0.3068 0.6404 0.1082 0.099 Uiso 1 1 calc R . . H18B H 0.3941 0.5309 0.1480 0.099 Uiso 1 1 calc R . . H18C H 0.3313 0.5924 0.2146 0.099 Uiso 1 1 calc R . . C19A C 0.4785(3) 0.2501(4) -0.0113(3) 0.0798(11) Uani 1 1 d . . . H19A H 0.5505 0.2040 -0.0110 0.096 Uiso 1 1 calc R . . H19B H 0.5053 0.3253 0.0204 0.096 Uiso 1 1 calc R . . C20A C 0.0874(4) 0.6388(5) 0.1758(3) 0.0919(13) Uani 1 1 d . . . C21A C 0.0893(4) 0.5790(4) 0.2676(3) 0.1116(16) Uani 1 1 d . . . H21A H 0.0427 0.6248 0.2979 0.167 Uiso 1 1 calc R . . H21B H 0.1756 0.5704 0.3130 0.167 Uiso 1 1 calc R . . H21C H 0.0507 0.5032 0.2510 0.167 Uiso 1 1 calc R . . O1B O 1.3780(2) 0.6467(3) 0.68116(16) 0.0907(9) Uani 1 1 d . . . O2B O 0.3722(2) 0.4270(2) 0.5120(2) 0.0869(8) Uani 1 1 d . . . C1B C 1.0985(3) 0.7882(3) 0.6913(2) 0.0618(9) Uani 1 1 d . . . H1B1 H 1.0558 0.7922 0.7379 0.074 Uiso 1 1 calc R . . H1B2 H 1.1353 0.8642 0.6891 0.074 Uiso 1 1 calc R . . C2B C 1.2024(3) 0.6965(3) 0.7247(2) 0.0647(10) Uani 1 1 d . . . H2B1 H 1.2661 0.7207 0.7875 0.078 Uiso 1 1 calc R . . H2B2 H 1.1661 0.6235 0.7356 0.078 Uiso 1 1 calc R . . C3B C 1.2662(3) 0.6758(3) 0.6525(2) 0.0593(9) Uani 1 1 d . . . C4B C 1.1906(3) 0.6909(3) 0.5479(2) 0.0524(8) Uani 1 1 d . . . H4B H 1.2260 0.6791 0.5003 0.063 Uiso 1 1 calc R . . C5B C 1.0703(3) 0.7218(2) 0.5221(2) 0.0432(7) Uani 1 1 d . . . C6B C 0.9599(3) 0.7661(3) 0.4336(2) 0.0493(8) Uani 1 1 d . . . H6B H 0.9810 0.8028 0.3808 0.059 Uiso 1 1 calc R . . C7B C 0.8554(2) 0.6721(3) 0.40165(19) 0.0473(7) Uani 1 1 d . . . H7B1 H 0.7869 0.6970 0.3417 0.057 Uiso 1 1 calc R . . H7B2 H 0.8899 0.5997 0.3876 0.057 Uiso 1 1 calc R . . C8B C 0.8036(2) 0.6516(2) 0.48271(19) 0.0393(7) Uani 1 1 d . . . H8B H 0.7469 0.7174 0.4797 0.047 Uiso 1 1 calc R . . C9B C 0.9102(2) 0.6557(3) 0.58612(18) 0.0401(7) Uani 1 1 d . . . H9B H 0.9582 0.5827 0.5937 0.048 Uiso 1 1 calc R . . C10B C 1.0038(2) 0.7565(3) 0.5896(2) 0.0429(7) Uani 1 1 d . . . C11B C 0.8530(3) 0.6549(3) 0.6654(2) 0.0501(8) Uani 1 1 d . . . H11C H 0.8046 0.7261 0.6607 0.060 Uiso 1 1 calc R . . H11D H 0.9209 0.6532 0.7302 0.060 Uiso 1 1 calc R . . C12B C 0.7659(3) 0.5489(3) 0.6547(2) 0.0546(8) Uani 1 1 d . . . H12C H 0.8167 0.4782 0.6683 0.066 Uiso 1 1 calc R . . H12D H 0.7265 0.5545 0.7034 0.066 Uiso 1 1 calc R . . C13B C 0.6622(2) 0.5400(2) 0.5519(2) 0.0398(7) Uani 1 1 d . . . C14B C 0.7266(2) 0.5421(2) 0.47557(19) 0.0399(7) Uani 1 1 d . . . H14B H 0.7869 0.4767 0.4922 0.048 Uiso 1 1 calc R . . C15B C 0.6199(3) 0.5097(3) 0.3789(2) 0.0580(9) Uani 1 1 d . . . H15C H 0.6535 0.4743 0.3332 0.070 Uiso 1 1 calc R . . H15D H 0.5704 0.5781 0.3479 0.070 Uiso 1 1 calc R . . C16B C 0.5390(3) 0.4223(3) 0.4096(2) 0.0631(9) Uani 1 1 d . . . H16C H 0.5478 0.3445 0.3863 0.076 Uiso 1 1 calc R . . H16D H 0.4501 0.4444 0.3815 0.076 Uiso 1 1 calc R . . C17B C 0.5870(3) 0.4241(3) 0.5230(2) 0.0480(7) Uani 1 1 d . . . H17B H 0.6468 0.3591 0.5484 0.058 Uiso 1 1 calc R . . C18B C 0.5680(3) 0.6398(3) 0.5376(2) 0.0579(9) Uani 1 1 d . . . H18D H 0.6124 0.7131 0.5486 0.087 Uiso 1 1 calc R . . H18E H 0.5263 0.6316 0.5839 0.087 Uiso 1 1 calc R . . H18F H 0.5057 0.6377 0.4714 0.087 Uiso 1 1 calc R . . C19B C 0.9380(3) 0.8501(3) 0.5099(2) 0.0570(8) Uani 1 1 d . . . H19C H 0.9842 0.9233 0.5191 0.068 Uiso 1 1 calc R . . H19D H 0.8492 0.8631 0.4990 0.068 Uiso 1 1 calc R . . C20B C 0.4821(4) 0.4114(3) 0.5625(3) 0.0623(9) Uani 1 1 d . . . C21B C 0.5195(3) 0.3783(3) 0.6689(3) 0.0923(13) Uani 1 1 d . . . H21D H 0.4462 0.3499 0.6801 0.138 Uiso 1 1 calc R . . H21E H 0.5529 0.4456 0.7097 0.138 Uiso 1 1 calc R . . H21F H 0.5832 0.3183 0.6852 0.138 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1A 0.123(2) 0.0685(18) 0.0813(19) -0.0223(16) 0.0233(16) -0.0216(17) O2A 0.238(4) 0.077(2) 0.184(4) -0.022(3) 0.116(3) 0.022(3) C1A 0.069(2) 0.068(3) 0.058(2) -0.013(2) -0.0006(18) 0.021(2) C2A 0.089(3) 0.060(2) 0.055(2) 0.0003(19) 0.0130(19) 0.015(2) C3A 0.066(2) 0.056(2) 0.063(2) -0.014(2) 0.0166(19) 0.0072(19) C4A 0.074(2) 0.071(3) 0.044(2) -0.014(2) 0.0149(18) 0.000(2) C5A 0.0496(19) 0.067(2) 0.050(2) -0.0133(18) 0.0185(16) 0.0035(18) C6A 0.075(2) 0.089(3) 0.062(2) -0.013(2) 0.042(2) -0.009(2) C7A 0.071(2) 0.073(2) 0.053(2) 0.0024(18) 0.0320(18) -0.0084(19) C8A 0.0434(17) 0.054(2) 0.0444(18) -0.0016(16) 0.0168(14) -0.0087(15) C9A 0.0412(17) 0.0535(19) 0.0401(17) -0.0046(15) 0.0086(14) -0.0023(14) C10A 0.0442(17) 0.062(2) 0.053(2) -0.0105(18) 0.0084(15) 0.0024(17) C11A 0.073(2) 0.055(2) 0.045(2) 0.0016(16) 0.0156(17) 0.0046(17) C12A 0.074(2) 0.051(2) 0.0485(19) -0.0021(17) 0.0286(17) -0.0037(18) C13A 0.0466(18) 0.0490(19) 0.056(2) 0.0026(16) 0.0237(15) 0.0007(15) C14A 0.0427(17) 0.055(2) 0.0494(19) 0.0037(16) 0.0172(15) -0.0059(15) C15A 0.070(2) 0.070(3) 0.069(2) 0.019(2) 0.026(2) 0.0083(19) C16A 0.078(3) 0.071(3) 0.102(3) 0.021(2) 0.038(2) 0.019(2) C17A 0.058(2) 0.058(2) 0.081(3) 0.001(2) 0.0342(18) 0.0005(17) C18A 0.068(2) 0.061(2) 0.072(2) -0.0103(19) 0.0299(18) -0.0082(18) C19A 0.054(2) 0.088(3) 0.103(3) -0.026(2) 0.035(2) -0.002(2) C20A 0.093(3) 0.077(3) 0.127(4) -0.010(3) 0.067(3) 0.013(3) C21A 0.133(4) 0.130(4) 0.100(3) -0.019(3) 0.076(3) 0.007(3) O1B 0.0498(14) 0.143(3) 0.0719(17) 0.0095(16) 0.0136(12) 0.0210(17) O2B 0.0623(16) 0.0846(18) 0.127(2) -0.0261(17) 0.0502(16) -0.0231(15) C1B 0.0497(19) 0.076(2) 0.064(2) -0.0251(19) 0.0254(17) -0.0184(18) C2B 0.0484(18) 0.096(3) 0.0450(19) -0.0081(19) 0.0119(15) -0.008(2) C3B 0.0419(18) 0.073(2) 0.060(2) 0.0028(18) 0.0144(16) 0.0025(17) C4B 0.0427(18) 0.072(2) 0.0479(19) 0.0001(17) 0.0236(15) 0.0003(16) C5B 0.0409(17) 0.0421(17) 0.0477(18) 0.0000(14) 0.0178(15) -0.0084(13) C6B 0.0466(18) 0.0535(19) 0.0494(19) 0.0093(17) 0.0196(15) -0.0048(16) C7B 0.0440(16) 0.0554(19) 0.0387(17) 0.0050(15) 0.0110(13) 0.0022(15) C8B 0.0348(15) 0.0425(18) 0.0414(16) -0.0007(14) 0.0152(13) 0.0036(13) C9B 0.0365(14) 0.0427(17) 0.0421(16) -0.0053(14) 0.0160(13) 0.0012(13) C10B 0.0379(16) 0.0459(18) 0.0463(18) -0.0101(15) 0.0172(14) -0.0048(14) C11B 0.0471(17) 0.062(2) 0.0407(17) -0.0076(15) 0.0161(14) -0.0080(16) C12B 0.0597(19) 0.059(2) 0.051(2) -0.0028(17) 0.0280(16) -0.0047(17) C13B 0.0373(15) 0.0389(17) 0.0460(17) -0.0065(14) 0.0188(14) -0.0017(13) C14B 0.0384(15) 0.0370(16) 0.0447(17) -0.0052(14) 0.0159(14) 0.0027(13) C15B 0.0490(18) 0.071(2) 0.053(2) -0.0091(17) 0.0175(16) -0.0117(17) C16B 0.056(2) 0.067(2) 0.069(2) -0.0181(19) 0.0268(18) -0.0231(18) C17B 0.0494(17) 0.0398(17) 0.060(2) -0.0047(15) 0.0261(16) -0.0031(14) C18B 0.0536(19) 0.0452(19) 0.084(2) -0.0043(18) 0.0358(17) 0.0003(16) C19B 0.0488(18) 0.0421(18) 0.082(2) 0.0033(18) 0.0259(17) -0.0059(15) C20B 0.069(2) 0.0439(19) 0.088(3) -0.020(2) 0.046(2) -0.0220(18) C21B 0.121(3) 0.091(3) 0.091(3) -0.008(3) 0.070(3) -0.034(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C3A 1.205(4) . ? O2A C20A 1.194(5) . ? C1A C10A 1.504(4) . ? C1A C2A 1.521(5) . ? C1A H1A1 0.9700 . ? C1A H1A2 0.9700 . ? C2A C3A 1.501(4) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.461(5) . ? C4A C5A 1.317(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.487(5) . ? C5A C10A 1.497(4) . ? C6A C7A 1.530(5) . ? C6A C19A 1.569(5) . ? C6A H6A 0.9800 . ? C7A C8A 1.539(4) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A C14A 1.507(4) . ? C8A C9A 1.530(4) . ? C8A H8A 0.9800 . ? C9A C11A 1.529(4) . ? C9A C10A 1.540(4) . ? C9A H9A 0.9800 . ? C10A C19A 1.564(5) . ? C11A C12A 1.526(4) . ? C11A H11A 0.9700 . ? C11A H11B 0.9700 . ? C12A C13A 1.520(4) . ? C12A H12A 0.9700 . ? C12A H12B 0.9700 . ? C13A C18A 1.533(4) . ? C13A C14A 1.538(4) . ? C13A C17A 1.550(4) . ? C14A C15A 1.515(4) . ? C14A H14A 0.9800 . ? C15A C16A 1.538(4) . ? C15A H15A 0.9700 . ? C15A H15B 0.9700 . ? C16A C17A 1.533(4) . ? C16A H16A 0.9700 . ? C16A H16B 0.9700 . ? C17A C20A 1.503(5) . ? C17A H17A 0.9800 . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C19A H19A 0.9700 . ? C19A H19B 0.9700 . ? C20A C21A 1.496(6) . ? C21A H21A 0.9600 . ? C21A H21B 0.9600 . ? C21A H21C 0.9600 . ? O1B C3B 1.223(3) . ? O2B C20B 1.201(4) . ? C1B C10B 1.514(4) . ? C1B C2B 1.515(4) . ? C1B H1B1 0.9700 . ? C1B H1B2 0.9700 . ? C2B C3B 1.500(4) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B C4B 1.454(4) . ? C4B C5B 1.320(3) . ? C4B H4B 0.9300 . ? C5B C10B 1.496(4) . ? C5B C6B 1.511(4) . ? C6B C7B 1.538(4) . ? C6B C19B 1.557(4) . ? C6B H6B 0.9800 . ? C7B C8B 1.519(3) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B C14B 1.508(3) . ? C8B C9B 1.541(3) . ? C8B H8B 0.9800 . ? C9B C11B 1.520(3) . ? C9B C10B 1.554(4) . ? C9B H9B 0.9800 . ? C10B C19B 1.550(4) . ? C11B C12B 1.534(4) . ? C11B H11C 0.9700 . ? C11B H11D 0.9700 . ? C12B C13B 1.523(4) . ? C12B H12C 0.9700 . ? C12B H12D 0.9700 . ? C13B C18B 1.524(4) . ? C13B C14B 1.540(3) . ? C13B C17B 1.547(4) . ? C14B C15B 1.520(3) . ? C14B H14B 0.9800 . ? C15B C16B 1.531(4) . ? C15B H15C 0.9700 . ? C15B H15D 0.9700 . ? C16B C17B 1.535(4) . ? C16B H16C 0.9700 . ? C16B H16D 0.9700 . ? C17B C20B 1.508(4) . ? C17B H17B 0.9800 . ? C18B H18D 0.9600 . ? C18B H18E 0.9600 . ? C18B H18F 0.9600 . ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C20B C21B 1.495(4) . ? C21B H21D 0.9600 . ? C21B H21E 0.9600 . ? C21B H21F 0.9600 . ? 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 C10A C1A C2A 109.2(3) . . ? C10A C1A H1A1 109.8 . . ? C2A C1A H1A1 109.8 . . ? C10A C1A H1A2 109.8 . . ? C2A C1A H1A2 109.8 . . ? H1A1 C1A H1A2 108.3 . . ? C3A C2A C1A 114.6(3) . . ? C3A C2A H2A1 108.6 . . ? C1A C2A H2A1 108.6 . . ? C3A C2A H2A2 108.6 . . ? C1A C2A H2A2 108.6 . . ? H2A1 C2A H2A2 107.6 . . ? O1A C3A C4A 121.8(3) . . ? O1A C3A C2A 121.3(4) . . ? C4A C3A C2A 116.9(3) . . ? C5A C4A C3A 118.6(3) . . ? C5A C4A H4A 120.7 . . ? C3A C4A H4A 120.7 . . ? C4A C5A C6A 141.1(3) . . ? C4A C5A C10A 127.1(3) . . ? C6A C5A C10A 90.8(3) . . ? C5A C6A C7A 109.3(2) . . ? C5A C6A C19A 84.9(3) . . ? C7A C6A C19A 111.9(3) . . ? C5A C6A H6A 115.6 . . ? C7A C6A H6A 115.6 . . ? C19A C6A H6A 115.6 . . ? C6A C7A C8A 109.0(3) . . ? C6A C7A H7A1 109.9 . . ? C8A C7A H7A1 109.9 . . ? C6A C7A H7A2 109.9 . . ? C8A C7A H7A2 109.9 . . ? H7A1 C7A H7A2 108.3 . . ? C14A C8A C9A 108.6(2) . . ? C14A C8A C7A 117.2(2) . . ? C9A C8A C7A 110.7(2) . . ? C14A C8A H8A 106.6 . . ? C9A C8A H8A 106.6 . . ? C7A C8A H8A 106.6 . . ? C11A C9A C8A 109.7(2) . . ? C11A C9A C10A 116.6(2) . . ? C8A C9A C10A 110.7(2) . . ? C11A C9A H9A 106.4 . . ? C8A C9A H9A 106.4 . . ? C10A C9A H9A 106.4 . . ? C5A C10A C1A 110.3(3) . . ? C5A C10A C9A 107.6(2) . . ? C1A C10A C9A 117.2(3) . . ? C5A C10A C19A 84.7(2) . . ? C1A C10A C19A 121.6(3) . . ? C9A C10A C19A 110.1(3) . . ? C12A C11A C9A 111.3(2) . . ? C12A C11A H11A 109.4 . . ? C9A C11A H11A 109.4 . . ? C12A C11A H11B 109.4 . . ? C9A C11A H11B 109.4 . . ? H11A C11A H11B 108.0 . . ? C13A C12A C11A 113.3(2) . . ? C13A C12A H12A 108.9 . . ? C11A C12A H12A 108.9 . . ? C13A C12A H12B 108.9 . . ? C11A C12A H12B 108.9 . . ? H12A C12A H12B 107.7 . . ? C12A C13A C18A 110.1(2) . . ? C12A C13A C14A 108.2(2) . . ? C18A C13A C14A 112.9(2) . . ? C12A C13A C17A 117.5(2) . . ? C18A C13A C17A 108.7(3) . . ? C14A C13A C17A 99.1(2) . . ? C8A C14A C15A 121.0(2) . . ? C8A C14A C13A 112.4(2) . . ? C15A C14A C13A 104.3(2) . . ? C8A C14A H14A 106.1 . . ? C15A C14A H14A 106.1 . . ? C13A C14A H14A 106.1 . . ? C14A C15A C16A 103.7(3) . . ? C14A C15A H15A 111.0 . . ? C16A C15A H15A 111.0 . . ? C14A C15A H15B 111.0 . . ? C16A C15A H15B 111.0 . . ? H15A C15A H15B 109.0 . . ? C17A C16A C15A 106.5(3) . . ? C17A C16A H16A 110.4 . . ? C15A C16A H16A 110.4 . . ? C17A C16A H16B 110.4 . . ? C15A C16A H16B 110.4 . . ? H16A C16A H16B 108.6 . . ? C20A C17A C16A 114.6(3) . . ? C20A C17A C13A 115.3(3) . . ? C16A C17A C13A 104.8(2) . . ? C20A C17A H17A 107.2 . . ? C16A C17A H17A 107.2 . . ? C13A C17A H17A 107.2 . . ? C13A C18A H18A 109.5 . . ? C13A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C13A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C10A C19A C6A 85.4(2) . . ? C10A C19A H19A 114.4 . . ? C6A C19A H19A 114.4 . . ? C10A C19A H19B 114.4 . . ? C6A C19A H19B 114.4 . . ? H19A C19A H19B 111.5 . . ? O2A C20A C21A 119.7(5) . . ? O2A C20A C17A 122.4(5) . . ? C21A C20A C17A 117.8(4) . . ? C20A C21A H21A 109.5 . . ? C20A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? C20A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? C10B C1B C2B 109.3(3) . . ? C10B C1B H1B1 109.8 . . ? C2B C1B H1B1 109.8 . . ? C10B C1B H1B2 109.8 . . ? C2B C1B H1B2 109.8 . . ? H1B1 C1B H1B2 108.3 . . ? C3B C2B C1B 113.8(3) . . ? C3B C2B H2B1 108.8 . . ? C1B C2B H2B1 108.8 . . ? C3B C2B H2B2 108.8 . . ? C1B C2B H2B2 108.8 . . ? H2B1 C2B H2B2 107.7 . . ? O1B C3B C4B 121.4(3) . . ? O1B C3B C2B 120.8(3) . . ? C4B C3B C2B 117.8(3) . . ? C5B C4B C3B 118.2(3) . . ? C5B C4B H4B 120.9 . . ? C3B C4B H4B 120.9 . . ? C4B C5B C10B 127.1(3) . . ? C4B C5B C6B 140.5(3) . . ? C10B C5B C6B 90.7(2) . . ? C5B C6B C7B 108.9(2) . . ? C5B C6B C19B 84.2(2) . . ? C7B C6B C19B 109.7(2) . . ? C5B C6B H6B 116.5 . . ? C7B C6B H6B 116.5 . . ? C19B C6B H6B 116.5 . . ? C8B C7B C6B 110.5(2) . . ? C8B C7B H7B1 109.6 . . ? C6B C7B H7B1 109.6 . . ? C8B C7B H7B2 109.6 . . ? C6B C7B H7B2 109.6 . . ? H7B1 C7B H7B2 108.1 . . ? C14B C8B C7B 117.1(2) . . ? C14B C8B C9B 108.4(2) . . ? C7B C8B C9B 111.5(2) . . ? C14B C8B H8B 106.4 . . ? C7B C8B H8B 106.4 . . ? C9B C8B H8B 106.4 . . ? C11B C9B C8B 110.0(2) . . ? C11B C9B C10B 117.3(2) . . ? C8B C9B C10B 109.3(2) . . ? C11B C9B H9B 106.5 . . ? C8B C9B H9B 106.5 . . ? C10B C9B H9B 106.5 . . ? C5B C10B C1B 111.0(2) . . ? C5B C10B C19B 84.9(2) . . ? C1B C10B C19B 122.3(3) . . ? C5B C10B C9B 106.7(2) . . ? C1B C10B C9B 115.8(2) . . ? C19B C10B C9B 110.8(2) . . ? C9B C11B C12B 111.6(2) . . ? C9B C11B H11C 109.3 . . ? C12B C11B H11C 109.3 . . ? C9B C11B H11D 109.3 . . ? C12B C11B H11D 109.3 . . ? H11C C11B H11D 108.0 . . ? C13B C12B C11B 112.6(2) . . ? C13B C12B H12C 109.1 . . ? C11B C12B H12C 109.1 . . ? C13B C12B H12D 109.1 . . ? C11B C12B H12D 109.1 . . ? H12C C12B H12D 107.8 . . ? C12B C13B C18B 109.2(2) . . ? C12B C13B C14B 108.0(2) . . ? C18B C13B C14B 112.7(2) . . ? C12B C13B C17B 118.0(2) . . ? C18B C13B C17B 108.6(2) . . ? C14B C13B C17B 100.2(2) . . ? C8B C14B C15B 120.4(2) . . ? C8B C14B C13B 112.4(2) . . ? C15B C14B C13B 103.8(2) . . ? C8B C14B H14B 106.5 . . ? C15B C14B H14B 106.5 . . ? C13B C14B H14B 106.5 . . ? C14B C15B C16B 104.1(2) . . ? C14B C15B H15C 110.9 . . ? C16B C15B H15C 110.9 . . ? C14B C15B H15D 110.9 . . ? C16B C15B H15D 110.9 . . ? H15C C15B H15D 108.9 . . ? C15B C16B C17B 107.1(2) . . ? C15B C16B H16C 110.3 . . ? C17B C16B H16C 110.3 . . ? C15B C16B H16D 110.3 . . ? C17B C16B H16D 110.3 . . ? H16C C16B H16D 108.5 . . ? C20B C17B C16B 113.3(3) . . ? C20B C17B C13B 114.3(2) . . ? C16B C17B C13B 104.1(2) . . ? C20B C17B H17B 108.3 . . ? C16B C17B H17B 108.3 . . ? C13B C17B H17B 108.3 . . ? C13B C18B H18D 109.5 . . ? C13B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C13B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C10B C19B C6B 87.0(2) . . ? C10B C19B H19C 114.1 . . ? C6B C19B H19C 114.1 . . ? C10B C19B H19D 114.1 . . ? C6B C19B H19D 114.1 . . ? H19C C19B H19D 111.3 . . ? O2B C20B C21B 120.0(3) . . ? O2B C20B C17B 122.5(3) . . ? C21B C20B C17B 117.5(3) . . ? C20B C21B H21D 109.5 . . ? C20B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? C20B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.128 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.027