# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'Baggio, Ricardo F.' 'Burton, Gerardo' 'Garland, M. Teresa' 'Ghini, Alberto A.' 'Nicoletti, Daniel' _publ_contact_author 'Prof Gerardo Burton' _publ_contact_author_address ; Burton, Gerardo Departamento de Qu\'imica Org\'anica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabell\'on II, 1428 Buenos Aires, Argentina. ; _publ_contact_author_phone 54-11-4576_3385 _publ_contact_author_fax 54-11-4576-3385 _publ_contact_author_email 'burton@qo.fcen.uba.ar' _publ_requested_journal 'J.Chem.Soc., Perkin Trans. 1' _publ_section_title ; Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives ; _publ_section_references ; Allen,F.H. & Kennard,O. (1993). Chemical Dessign Automation News, 8, 131-137. Nardelli,M. (1983). Comp.Chem. 7, 95-98. Sheldrick,G.M.(1994). SHELXTL-PC. version 5.0 Siemens Analytical x-ray Instruments, Inc., Madison, Wisconsin, USA. Sheldrick,G.M.(1997). SHELXL-97. Program for Structure Refinement, Univ. of G\"ottingen, Germany. Sheldrick,G.M.(1997). SHELXS-97. Program for Structure Resolution, Univ. of G\"ottingen, Germany. Siemens P3/P4-PC version v4.27. (1991). Siemens Analytical x-ray Instruments, Inc., Madison, Wisconsin, USA. ; data_betaepoxide _database_code_CSD 161559 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (20R)-13\b,14\b-oxido-20-hydroxy-17(13->18)abeo-4-pregnen-3-one ; _chemical_formula_moiety 'C21 H30 O3' _chemical_formula_sum 'C21 H30 O3' _chemical_formula_weight 330.45 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 7.976(3) _cell_length_b 9.399(4) _cell_length_c 24.084(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1805.5(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 12.5 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(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 'Siemens R3m' _diffrn_measurement_method \w/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_decay_% <2 _diffrn_reflns_number 1975 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_av_sigmaI/netI 0.086 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1851 _reflns_number_gt 1053 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Siemens P3/P4-PC version V4.27 (1991)' _computing_data_reduction 'XDISK in SHELXTL/PC(Sheldrick,1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC(Sheldrick,1994)' _computing_publication_material ; PARST (Nardelli, 1983) and CSD (Allen, Kennard & Taylor, 1983) ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 1851 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1194 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max <0.001 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1811(6) 0.2093(6) 0.3672(2) 0.0445(13) Uani 1 d . . . H1A H 1.2433 0.1299 0.3517 0.041(14) Uiso 1 calc R . . H1B H 1.2004 0.2911 0.3435 0.026(12) Uiso 1 calc R . . C2 C 1.2490(6) 0.2414(6) 0.4247(2) 0.0539(16) Uani 1 d . . . H2C H 1.2426 0.1565 0.4475 0.09(2) Uiso 1 calc R . . H2D H 1.3659 0.2690 0.4219 0.049(15) Uiso 1 calc R . . C3 C 1.1515(7) 0.3586(6) 0.4516(2) 0.0435(14) Uani 1 d . . . C4 C 0.9767(6) 0.3691(6) 0.43737(19) 0.0419(13) Uani 1 d . . . H4B H 0.9131 0.4393 0.4546 0.043(14) Uiso 1 calc R . . C5 C 0.8998(6) 0.2834(6) 0.4006(2) 0.0375(12) Uani 1 d . . . C6 C 0.7135(6) 0.2903(6) 0.39354(18) 0.0432(13) Uani 1 d . . . H6A H 0.6712 0.3733 0.4129 0.045(14) Uiso 1 calc R . . H6B H 0.6635 0.2068 0.4105 0.030(12) Uiso 1 calc R . . C7 C 0.6602(6) 0.2978(5) 0.33288(19) 0.0441(14) Uani 1 d . . . H7C H 0.6972 0.3873 0.3170 0.037(13) Uiso 1 calc R . . H7D H 0.5389 0.2941 0.3305 0.031(12) Uiso 1 calc R . . C8 C 0.7366(5) 0.1729(5) 0.29972(18) 0.0347(12) Uani 1 d . . . H8C H 0.7018 0.0848 0.3182 0.047(14) Uiso 1 calc R . . C9 C 0.9287(5) 0.1824(5) 0.30475(17) 0.0313(11) Uani 1 d . . . H9B H 0.9605 0.2769 0.2911 0.029(11) Uiso 1 calc R . . C10 C 0.9933(6) 0.1730(5) 0.36625(19) 0.0374(12) Uani 1 d . . . C11 C 1.0106(7) 0.0747(5) 0.26582(17) 0.0459(13) Uani 1 d . . . H11C H 1.1305 0.0718 0.2724 0.063(17) Uiso 1 calc R . . H11D H 0.9654 -0.0194 0.2728 0.036(13) Uiso 1 calc R . . C12 C 0.9765(6) 0.1173(5) 0.20579(17) 0.0406(13) Uani 1 d . . . H12C H 1.0359 0.2051 0.1978 0.036(13) Uiso 1 calc R . . H12D H 1.0204 0.0443 0.1813 0.034(12) Uiso 1 calc R . . C13 C 0.7938(6) 0.1381(5) 0.19372(19) 0.0383(12) Uani 1 d . . . C14 C 0.6747(6) 0.1645(5) 0.23952(19) 0.0374(12) Uani 1 d . . . C15 C 0.5088(6) 0.2335(6) 0.22696(19) 0.0479(14) Uani 1 d . . . H15C H 0.5130 0.3321 0.2389 0.078(19) Uiso 1 calc R . . H15D H 0.4222 0.1863 0.2484 0.017(11) Uiso 1 calc R . . C16 C 0.4606(6) 0.2289(6) 0.16548(19) 0.0496(14) Uani 1 d . . . H16C H 0.4345 0.1320 0.1547 0.09(2) Uiso 1 calc R . . H16D H 0.3620 0.2871 0.1591 0.028(12) Uiso 1 calc R . . C17 C 0.6069(6) 0.2848(5) 0.13091(19) 0.0415(12) Uani 1 d . . . H17A H 0.6445 0.3726 0.1489 0.019(11) Uiso 1 calc R . . C18 C 0.7515(6) 0.1806(5) 0.13485(19) 0.0411(13) Uani 1 d . . . H18B H 0.7236 0.0958 0.1138 0.056(15) Uiso 1 calc R . . H18C H 0.8498 0.2231 0.1179 0.049(15) Uiso 1 calc R . . C19 C 0.9605(7) 0.0246(5) 0.3910(2) 0.0547(16) Uani 1 d . . . H19D H 1.0099 0.0189 0.4273 0.062(17) Uiso 1 calc R . . H19E H 1.0093 -0.0465 0.3674 0.048(15) Uiso 1 calc R . . H19F H 0.8418 0.0090 0.3937 0.09(2) Uiso 1 calc R . . C20 C 0.5620(7) 0.3241(6) 0.0715(2) 0.0515(15) Uani 1 d . . . H20B H 0.6656 0.3487 0.0519 0.041(14) Uiso 1 calc R . . C21 C 0.4729(10) 0.2096(7) 0.0388(2) 0.081(2) Uani 1 d . . . H21D H 0.4600 0.2400 0.0010 0.067(16) Uiso 1 calc R . . H21E H 0.3644 0.1925 0.0547 0.13(3) Uiso 1 calc R . . H21F H 0.5376 0.1235 0.0398 0.11(3) Uiso 1 calc R . . O22 O 1.2167(4) 0.4360(4) 0.48622(14) 0.0617(11) Uani 1 d . . . O23 O 0.6908(4) 0.0241(3) 0.21563(13) 0.0482(9) Uani 1 d . . . O24 O 0.4612(6) 0.4493(4) 0.07546(15) 0.0711(13) Uani 1 d . . . H24 H 0.382(8) 0.466(8) 0.042(2) 0.12(3) Uiso 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.038(3) 0.045(3) 0.051(3) 0.000(3) 0.000(3) 0.005(3) C2 0.038(3) 0.069(4) 0.055(3) -0.008(3) -0.003(3) 0.003(3) C3 0.050(4) 0.052(4) 0.028(3) 0.008(3) 0.006(3) -0.001(3) C4 0.046(3) 0.045(3) 0.034(3) -0.008(3) 0.008(3) 0.003(3) C5 0.031(3) 0.045(3) 0.037(3) 0.005(3) 0.006(2) 0.002(3) C6 0.046(3) 0.048(3) 0.036(3) -0.001(3) 0.012(3) 0.008(3) C7 0.028(3) 0.052(4) 0.052(3) 0.001(3) 0.008(2) 0.003(3) C8 0.035(3) 0.028(3) 0.042(3) -0.002(2) 0.007(2) 0.002(2) C9 0.027(3) 0.032(3) 0.035(3) 0.001(2) 0.005(2) 0.001(2) C10 0.039(3) 0.032(3) 0.042(3) -0.001(2) 0.011(3) 0.003(3) C11 0.046(3) 0.040(3) 0.052(3) -0.003(3) -0.004(3) 0.006(3) C12 0.050(3) 0.036(3) 0.035(3) -0.009(2) 0.007(3) 0.010(3) C13 0.040(3) 0.030(3) 0.045(3) -0.002(2) 0.002(3) 0.002(3) C14 0.033(3) 0.033(3) 0.046(3) -0.008(2) 0.007(2) 0.000(3) C15 0.029(3) 0.060(4) 0.055(3) 0.004(3) 0.005(3) 0.002(3) C16 0.038(3) 0.056(4) 0.055(3) 0.005(3) -0.009(3) 0.004(3) C17 0.046(3) 0.037(3) 0.042(3) -0.009(3) -0.003(3) -0.004(3) C18 0.043(3) 0.038(3) 0.042(3) -0.005(3) 0.005(3) 0.001(3) C19 0.059(4) 0.046(3) 0.059(4) 0.009(3) 0.004(3) 0.013(3) C20 0.055(4) 0.050(3) 0.050(3) 0.004(3) 0.000(3) 0.007(3) C21 0.101(6) 0.083(5) 0.058(4) -0.010(4) -0.032(4) 0.006(5) O22 0.061(2) 0.077(3) 0.048(2) -0.016(2) -0.002(2) -0.008(2) O23 0.055(2) 0.0299(18) 0.060(2) -0.0012(17) -0.002(2) -0.0080(19) O24 0.092(3) 0.060(3) 0.061(3) 0.004(2) -0.012(3) 0.030(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.518(6) . ? C1 C10 1.537(6) . ? C2 C3 1.496(7) . ? C3 O22 1.222(6) . ? C3 C4 1.439(7) . ? C4 C5 1.345(6) . ? C5 C6 1.496(6) . ? C5 C10 1.522(6) . ? C6 C7 1.523(6) . ? C7 C8 1.545(6) . ? C8 C14 1.534(6) . ? C8 C9 1.540(6) . ? C9 C11 1.527(6) . ? C9 C10 1.571(6) . ? C10 C19 1.539(7) . ? C11 C12 1.525(6) . ? C12 C13 1.499(6) . ? C13 O23 1.449(5) . ? C13 C14 1.477(6) . ? C13 C18 1.511(6) . ? C14 O23 1.445(5) . ? C14 C15 1.505(6) . ? C15 C16 1.530(6) . ? C16 C17 1.527(6) . ? C17 C18 1.516(6) . ? C17 C20 1.520(6) . ? C20 O24 1.428(6) . ? C20 C21 1.512(7) . ? 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(4) . . ? C3 C2 C1 110.9(5) . . ? O22 C3 C4 122.3(5) . . ? O22 C3 C2 120.8(5) . . ? C4 C3 C2 116.8(5) . . ? C5 C4 C3 123.9(5) . . ? C4 C5 C6 120.1(5) . . ? C4 C5 C10 122.8(5) . . ? C6 C5 C10 117.0(5) . . ? C5 C6 C7 112.8(4) . . ? C6 C7 C8 110.5(4) . . ? C14 C8 C9 113.4(4) . . ? C14 C8 C7 113.6(4) . . ? C9 C8 C7 107.9(4) . . ? C11 C9 C8 109.8(4) . . ? C11 C9 C10 113.7(4) . . ? C8 C9 C10 113.4(4) . . ? C5 C10 C1 108.6(4) . . ? C5 C10 C19 108.9(4) . . ? C1 C10 C19 111.2(4) . . ? C5 C10 C9 108.2(4) . . ? C1 C10 C9 108.7(4) . . ? C19 C10 C9 111.1(4) . . ? C12 C11 C9 109.4(4) . . ? C13 C12 C11 113.0(4) . . ? O23 C13 C14 59.2(3) . . ? O23 C13 C12 112.6(4) . . ? C14 C13 C12 120.2(4) . . ? O23 C13 C18 114.2(4) . . ? C14 C13 C18 120.8(4) . . ? C12 C13 C18 115.7(4) . . ? O23 C14 C13 59.5(3) . . ? O23 C14 C15 113.1(4) . . ? C13 C14 C15 119.2(4) . . ? O23 C14 C8 113.3(4) . . ? C13 C14 C8 120.5(4) . . ? C15 C14 C8 116.8(4) . . ? C14 C15 C16 113.8(4) . . ? C17 C16 C15 109.0(4) . . ? C18 C17 C20 113.3(4) . . ? C18 C17 C16 109.0(4) . . ? C20 C17 C16 114.6(4) . . ? C13 C18 C17 113.5(4) . . ? O24 C20 C21 110.9(5) . . ? O24 C20 C17 105.7(4) . . ? C21 C20 C17 115.4(5) . . ? C14 O23 C13 61.4(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 -55.6(6) . . . . ? C1 C2 C3 O22 -152.2(5) . . . . ? C1 C2 C3 C4 31.6(7) . . . . ? O22 C3 C4 C5 -178.2(5) . . . . ? C2 C3 C4 C5 -2.1(7) . . . . ? C3 C4 C5 C6 172.4(5) . . . . ? C3 C4 C5 C10 -5.2(8) . . . . ? C4 C5 C6 C7 132.3(5) . . . . ? C10 C5 C6 C7 -50.0(6) . . . . ? C5 C6 C7 C8 54.5(6) . . . . ? C6 C7 C8 C14 174.2(4) . . . . ? C6 C7 C8 C9 -59.1(5) . . . . ? C14 C8 C9 C11 -44.9(5) . . . . ? C7 C8 C9 C11 -171.7(4) . . . . ? C14 C8 C9 C10 -173.2(4) . . . . ? C7 C8 C9 C10 60.0(5) . . . . ? C4 C5 C10 C1 -17.4(6) . . . . ? C6 C5 C10 C1 164.9(4) . . . . ? C4 C5 C10 C19 103.7(6) . . . . ? C6 C5 C10 C19 -73.9(6) . . . . ? C4 C5 C10 C9 -135.3(5) . . . . ? C6 C5 C10 C9 47.0(5) . . . . ? C2 C1 C10 C5 47.5(6) . . . . ? C2 C1 C10 C19 -72.3(6) . . . . ? C2 C1 C10 C9 165.0(4) . . . . ? C11 C9 C10 C5 -178.9(4) . . . . ? C8 C9 C10 C5 -52.6(5) . . . . ? C11 C9 C10 C1 63.3(5) . . . . ? C8 C9 C10 C1 -170.4(4) . . . . ? C11 C9 C10 C19 -59.4(5) . . . . ? C8 C9 C10 C19 67.0(5) . . . . ? C8 C9 C11 C12 66.9(5) . . . . ? C10 C9 C11 C12 -164.9(4) . . . . ? C9 C11 C12 C13 -53.8(6) . . . . ? C11 C12 C13 O23 -46.1(5) . . . . ? C11 C12 C13 C14 20.3(6) . . . . ? C11 C12 C13 C18 180.0(4) . . . . ? C12 C13 C14 O23 -99.8(5) . . . . ? C18 C13 C14 O23 101.5(5) . . . . ? O23 C13 C14 C15 -101.1(5) . . . . ? C12 C13 C14 C15 159.1(5) . . . . ? C18 C13 C14 C15 0.5(7) . . . . ? O23 C13 C14 C8 100.7(5) . . . . ? C12 C13 C14 C8 0.8(7) . . . . ? C18 C13 C14 C8 -157.8(4) . . . . ? C9 C8 C14 O23 79.0(5) . . . . ? C7 C8 C14 O23 -157.3(4) . . . . ? C9 C8 C14 C13 11.8(6) . . . . ? C7 C8 C14 C13 135.6(4) . . . . ? C9 C8 C14 C15 -147.0(4) . . . . ? C7 C8 C14 C15 -23.2(6) . . . . ? O23 C14 C15 C16 -49.5(6) . . . . ? C13 C14 C15 C16 17.3(7) . . . . ? C8 C14 C15 C16 176.4(4) . . . . ? C14 C15 C16 C17 -50.9(6) . . . . ? C15 C16 C17 C18 67.7(6) . . . . ? C15 C16 C17 C20 -164.2(4) . . . . ? O23 C13 C18 C17 83.4(5) . . . . ? C14 C13 C18 C17 16.1(6) . . . . ? C12 C13 C18 C17 -143.4(4) . . . . ? C20 C17 C18 C13 -178.5(4) . . . . ? C16 C17 C18 C13 -49.6(5) . . . . ? C18 C17 C20 O24 -163.8(4) . . . . ? C16 C17 C20 O24 70.2(5) . . . . ? C18 C17 C20 C21 73.3(6) . . . . ? C16 C17 C20 C21 -52.7(7) . . . . ? C15 C14 O23 C13 111.4(4) . . . . ? C8 C14 O23 C13 -112.8(4) . . . . ? C12 C13 O23 C14 112.7(4) . . . . ? C18 C13 O23 C14 -112.7(5) . . . . ? 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 O24 H24 O22 1.03(.06) 1.817(.063) 2.79(.01) 157.(5.) 2_644 # Symmetry code 2_664: -x+1/2+1,-y+1,+z-1/2 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.151 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.039 #===END data_methoxy _database_code_CSD 161560 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (20R)-13\b-methoxy-14\a-hydroxy-20-acetyloxy-17(13->18)abeo-4-pregnen-3-one ; _chemical_formula_moiety 'C24 H36 O5' _chemical_formula_sum 'C24 H36 O5' _chemical_formula_weight 404.53 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 7.518(2) _cell_length_b 16.476(6) _cell_length_c 17.818(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2207.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 12.5 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 293(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 'Siemens R3m' _diffrn_measurement_method \w/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_decay_% <2 _diffrn_reflns_number 2986 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.160 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2773 _reflns_number_gt 1248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/P4-PC version V4.27 (1991)' _computing_cell_refinement 'Siemens P3/P4-PC version V4.27 (1991)' _computing_data_reduction 'XDISK in SHELXTL/PC(Sheldrick,1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC(Sheldrick,1994)' _computing_publication_material ; PARST (Nardelli, 1983) and CSD (Allen, Kennard & Taylor, 1983) ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0280P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 2773 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1824 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 0.932 _refine_ls_restrained_S_all 0.932 _refine_ls_shift/su_max <0.001 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2301(10) 1.1798(3) 0.5614(3) 0.052(2) Uani 1 d . . . H1A H 0.3469 1.1549 0.5581 0.06(2) Uiso 1 calc R . . H1B H 0.2037 1.2036 0.5128 0.035(17) Uiso 1 calc R . . C2 C 0.2365(10) 1.2467(4) 0.6193(4) 0.058(2) Uani 1 d . . . H2A H 0.2720 1.2243 0.6673 0.034(17) Uiso 1 calc R . . H2B H 0.3244 1.2868 0.6046 0.10(3) Uiso 1 calc R . . C3 C 0.0604(12) 1.2863(3) 0.6269(4) 0.057(2) Uani 1 d . . . C4 C -0.0954(9) 1.2315(3) 0.6222(3) 0.0383(17) Uani 1 d . . . H4A H -0.2074 1.2521 0.6335 0.037(18) Uiso 1 calc R . . C5 C -0.0811(10) 1.1536(3) 0.6024(3) 0.043(2) Uani 1 d . . . C6 C -0.2409(9) 1.0991(3) 0.6062(3) 0.045(2) Uani 1 d . . . H6A H -0.2222 1.0590 0.6452 0.010(12) Uiso 1 calc R . . H6B H -0.3438 1.1313 0.6201 0.023(16) Uiso 1 calc R . . C7 C -0.2795(9) 1.0559(4) 0.5334(3) 0.0416(18) Uani 1 d . . . H7A H -0.3196 1.0950 0.4964 0.08(2) Uiso 1 calc R . . H7B H -0.3745 1.0170 0.5413 0.25(6) Uiso 1 calc R . . C8 C -0.1147(9) 1.0116(3) 0.5035(3) 0.0393(19) Uani 1 d . . . H8A H -0.0899 0.9662 0.5374 0.005(11) Uiso 1 calc R . . C9 C 0.0512(9) 1.0667(3) 0.5026(3) 0.0362(17) Uani 1 d . . . H9A H 0.0267 1.1089 0.4653 0.053(17) Uiso 1 calc R . . C10 C 0.0913(9) 1.1128(4) 0.5780(4) 0.0439(19) Uani 1 d . . . C11 C 0.2129(10) 1.0203(4) 0.4733(3) 0.053(2) Uani 1 d . . . H11A H 0.2432 0.9778 0.5087 0.08(2) Uiso 1 calc R . . H11B H 0.3133 1.0571 0.4701 0.046(19) Uiso 1 calc R . . C12 C 0.1808(10) 0.9822(4) 0.3959(3) 0.0465(19) Uani 1 d . . . H12A H 0.2851 0.9516 0.3809 0.07(2) Uiso 1 calc R . . H12B H 0.1616 1.0248 0.3591 0.06(2) Uiso 1 calc R . . C13 C 0.0172(10) 0.9255(3) 0.3979(3) 0.0332(16) Uani 1 d . . . C14 C -0.1459(9) 0.9759(3) 0.4242(3) 0.0322(17) Uani 1 d . . . C15 C -0.3090(10) 0.9221(4) 0.4205(3) 0.051(2) Uani 1 d . . . H15A H -0.4120 0.9530 0.4366 0.023(15) Uiso 1 calc R . . H15B H -0.2941 0.8771 0.4551 0.07(2) Uiso 1 calc R . . C16 C -0.3429(10) 0.8887(4) 0.3418(3) 0.053(2) Uani 1 d . . . H16A H -0.4494 0.8555 0.3428 0.044(18) Uiso 1 calc R . . H16B H -0.3645 0.9338 0.3079 0.044(18) Uiso 1 calc R . . C17 C -0.1902(9) 0.8386(3) 0.3117(3) 0.0392(18) Uani 1 d . . . H17A H -0.2093 0.8313 0.2577 0.008(11) Uiso 1 calc R . . C18 C -0.0180(9) 0.8891(3) 0.3220(3) 0.0375(16) Uani 1 d . . . H18A H 0.0822 0.8547 0.3093 0.019(15) Uiso 1 calc R . . H18B H -0.0203 0.9330 0.2857 0.049(17) Uiso 1 calc R . . C19 C 0.1519(11) 1.0549(4) 0.6387(3) 0.063(2) Uani 1 d . . . H19A H 0.1660 1.0839 0.6851 0.046(17) Uiso 1 calc R . . H19B H 0.2635 1.0310 0.6246 0.003(13) Uiso 1 calc R . . H19C H 0.0646 1.0129 0.6451 0.22(6) Uiso 1 calc R . . C20 C -0.1782(11) 0.7539(3) 0.3475(4) 0.057(2) Uani 1 d . . . H20A H -0.1543 0.7584 0.4014 0.022(14) Uiso 1 calc R . . C21 C -0.3478(11) 0.7046(4) 0.3340(6) 0.077(3) Uani 1 d . . . H21A H -0.3262 0.6487 0.3458 0.06(2) Uiso 1 calc R . . H21B H -0.3824 0.7093 0.2824 0.19(5) Uiso 1 calc R . . H21C H -0.4414 0.7251 0.3655 0.08(3) Uiso 1 calc R . . C22 C 0.0448(11) 0.6486(3) 0.3443(4) 0.0459(19) Uani 1 d . . . C23 C 0.1945(12) 0.6162(5) 0.3004(5) 0.072(2) Uani 1 d . . . H23A H 0.2261 0.5635 0.3191 0.14(4) Uiso 1 calc R . . H23B H 0.2946 0.6520 0.3047 0.25(7) Uiso 1 calc R . . H23C H 0.1603 0.6119 0.2486 0.20(5) Uiso 1 calc R . . C24 C 0.1948(11) 0.8164(4) 0.4511(4) 0.060(2) Uani 1 d . . . H24A H 0.1806 0.7682 0.4807 0.09(3) Uiso 1 calc R . . H24B H 0.2916 0.8480 0.4707 0.22(6) Uiso 1 calc R . . H24C H 0.2198 0.8018 0.4001 0.035(17) Uiso 1 calc R . . O25 O -0.0103(8) 0.6228(2) 0.4033(2) 0.0688(17) Uani 1 d . . . O26 O -0.0316(7) 0.7128(2) 0.3099(2) 0.0444(12) Uani 1 d . . . O27 O 0.0351(6) 0.8631(2) 0.45394(19) 0.0353(11) Uani 1 d . . . O28 O -0.1575(7) 1.0422(3) 0.3718(3) 0.0460(13) Uani 1 d D . . H28 H -0.264(4) 1.044(3) 0.354(3) 0.05(2) Uiso 1 d D . . O29 O 0.0407(7) 1.3585(2) 0.6377(2) 0.0591(14) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.031(5) 0.057(4) 0.067(5) -0.008(4) 0.007(5) -0.009(5) C2 0.051(6) 0.055(4) 0.068(5) -0.009(4) 0.014(6) -0.025(5) C3 0.067(7) 0.041(4) 0.063(4) -0.003(4) 0.003(6) -0.021(6) C4 0.016(4) 0.047(4) 0.052(4) -0.010(3) 0.011(4) -0.006(4) C5 0.044(6) 0.040(4) 0.044(4) -0.009(3) -0.008(4) -0.011(5) C6 0.038(5) 0.046(4) 0.050(4) -0.006(3) 0.017(5) -0.013(5) C7 0.017(4) 0.058(4) 0.050(4) -0.014(4) 0.014(4) -0.001(5) C8 0.043(5) 0.023(3) 0.053(4) -0.001(3) -0.011(4) -0.008(4) C9 0.016(4) 0.048(4) 0.044(4) -0.005(3) -0.003(4) -0.003(4) C10 0.030(5) 0.037(4) 0.064(5) 0.008(3) -0.006(4) -0.005(4) C11 0.028(6) 0.053(4) 0.078(5) 0.001(4) 0.003(5) -0.010(5) C12 0.035(5) 0.049(4) 0.055(4) -0.005(4) 0.018(5) 0.007(5) C13 0.033(5) 0.038(3) 0.028(3) 0.010(3) -0.004(4) 0.009(4) C14 0.022(4) 0.032(3) 0.043(4) -0.003(3) -0.008(4) 0.000(4) C15 0.031(5) 0.077(5) 0.047(4) -0.031(4) 0.002(5) 0.008(5) C16 0.029(5) 0.069(4) 0.060(5) -0.012(4) 0.007(5) -0.010(5) C17 0.042(5) 0.050(4) 0.026(3) 0.000(3) 0.004(4) 0.002(5) C18 0.022(4) 0.044(3) 0.047(4) 0.007(3) -0.003(4) 0.006(5) C19 0.050(6) 0.070(4) 0.069(5) -0.021(4) -0.027(5) 0.021(6) C20 0.076(7) 0.045(4) 0.051(4) 0.004(3) -0.008(6) -0.015(6) C21 0.046(6) 0.073(6) 0.114(8) -0.003(5) 0.001(7) -0.022(6) C22 0.046(6) 0.029(3) 0.063(4) 0.004(3) -0.008(5) -0.004(5) C23 0.067(7) 0.054(5) 0.095(7) -0.020(4) 0.023(6) 0.026(6) C24 0.050(6) 0.056(4) 0.074(6) 0.007(4) -0.001(6) 0.019(6) O25 0.070(4) 0.063(3) 0.073(3) 0.022(2) 0.008(4) 0.011(4) O26 0.044(3) 0.040(2) 0.049(2) -0.004(2) -0.001(3) 0.004(3) O27 0.018(3) 0.049(2) 0.039(2) 0.0021(19) -0.006(3) 0.000(3) O28 0.025(3) 0.060(3) 0.053(3) 0.021(2) -0.020(3) 0.006(3) O29 0.051(4) 0.040(2) 0.087(3) 0.000(2) -0.004(4) -0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.511(7) . ? C1 C10 1.548(7) . ? C2 C3 1.482(9) . ? C3 O29 1.214(6) . ? C3 C4 1.482(9) . ? C4 C5 1.336(7) . ? C5 C6 1.501(8) . ? C5 C10 1.523(9) . ? C6 C7 1.507(7) . ? C7 C8 1.534(8) . ? C8 C9 1.543(8) . ? C8 C14 1.548(7) . ? C9 C11 1.527(8) . ? C9 C10 1.573(7) . ? C10 C19 1.513(7) . ? C11 C12 1.534(7) . ? C12 C13 1.545(8) . ? C13 O27 1.439(6) . ? C13 C18 1.503(7) . ? C13 C14 1.553(8) . ? C14 O28 1.441(6) . ? C14 C15 1.514(8) . ? C15 C16 1.528(7) . ? C16 C17 1.513(8) . ? C17 C18 1.550(8) . ? C17 C20 1.538(7) . ? C20 O26 1.456(7) . ? C20 C21 1.530(8) . ? C22 O25 1.207(7) . ? C22 O26 1.350(6) . ? C22 C23 1.471(9) . ? C24 O27 1.427(7) . ? 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 114.3(6) . . ? C3 C2 C1 110.8(7) . . ? O29 C3 C4 120.6(8) . . ? O29 C3 C2 123.7(7) . . ? C4 C3 C2 115.7(5) . . ? C5 C4 C3 122.5(7) . . ? C4 C5 C6 119.9(7) . . ? C4 C5 C10 124.6(7) . . ? C6 C5 C10 115.5(5) . . ? C7 C6 C5 113.5(5) . . ? C6 C7 C8 111.6(6) . . ? C7 C8 C9 112.1(5) . . ? C7 C8 C14 112.1(5) . . ? C9 C8 C14 109.7(5) . . ? C11 C9 C8 110.6(5) . . ? C11 C9 C10 112.4(6) . . ? C8 C9 C10 115.5(5) . . ? C19 C10 C5 109.3(6) . . ? C19 C10 C1 112.6(6) . . ? C5 C10 C1 108.3(5) . . ? C19 C10 C9 111.3(5) . . ? C5 C10 C9 107.1(6) . . ? C1 C10 C9 108.0(5) . . ? C9 C11 C12 112.8(6) . . ? C11 C12 C13 110.6(5) . . ? O27 C13 C18 110.9(4) . . ? O27 C13 C14 104.3(5) . . ? C18 C13 C14 110.2(6) . . ? O27 C13 C12 112.0(6) . . ? C18 C13 C12 111.1(5) . . ? C14 C13 C12 108.2(5) . . ? O28 C14 C15 111.5(6) . . ? O28 C14 C13 104.9(5) . . ? C15 C14 C13 108.3(5) . . ? O28 C14 C8 108.2(4) . . ? C15 C14 C8 112.6(5) . . ? C13 C14 C8 111.0(5) . . ? C14 C15 C16 112.7(6) . . ? C17 C16 C15 113.3(6) . . ? C16 C17 C18 107.4(5) . . ? C16 C17 C20 113.2(6) . . ? C18 C17 C20 112.9(6) . . ? C13 C18 C17 117.9(5) . . ? O26 C20 C21 108.2(5) . . ? O26 C20 C17 106.0(5) . . ? C21 C20 C17 111.5(7) . . ? O25 C22 O26 121.6(7) . . ? O25 C22 C23 126.7(7) . . ? O26 C22 C23 111.6(6) . . ? C22 O26 C20 118.5(5) . . ? C24 O27 C13 116.1(5) . . ? 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 -58.0(9) . . . . ? C1 C2 C3 O29 -143.2(6) . . . . ? C1 C2 C3 C4 38.2(9) . . . . ? O29 C3 C4 C5 172.6(5) . . . . ? C2 C3 C4 C5 -8.8(10) . . . . ? C3 C4 C5 C6 173.9(6) . . . . ? C3 C4 C5 C10 -3.7(9) . . . . ? C4 C5 C6 C7 126.0(6) . . . . ? C10 C5 C6 C7 -56.2(8) . . . . ? C5 C6 C7 C8 52.1(8) . . . . ? C6 C7 C8 C9 -49.1(8) . . . . ? C6 C7 C8 C14 -173.0(5) . . . . ? C7 C8 C9 C11 179.4(5) . . . . ? C14 C8 C9 C11 -55.4(7) . . . . ? C7 C8 C9 C10 50.3(7) . . . . ? C14 C8 C9 C10 175.5(5) . . . . ? C4 C5 C10 C19 109.1(7) . . . . ? C6 C5 C10 C19 -68.6(7) . . . . ? C4 C5 C10 C1 -13.9(9) . . . . ? C6 C5 C10 C1 168.4(5) . . . . ? C4 C5 C10 C9 -130.2(6) . . . . ? C6 C5 C10 C9 52.1(7) . . . . ? C2 C1 C10 C19 -76.6(8) . . . . ? C2 C1 C10 C5 44.4(8) . . . . ? C2 C1 C10 C9 160.0(6) . . . . ? C11 C9 C10 C19 -58.6(8) . . . . ? C8 C9 C10 C19 69.7(8) . . . . ? C11 C9 C10 C5 -178.0(5) . . . . ? C8 C9 C10 C5 -49.8(7) . . . . ? C11 C9 C10 C1 65.6(7) . . . . ? C8 C9 C10 C1 -166.2(5) . . . . ? C8 C9 C11 C12 55.0(7) . . . . ? C10 C9 C11 C12 -174.3(5) . . . . ? C9 C11 C12 C13 -56.6(8) . . . . ? C11 C12 C13 O27 -56.7(7) . . . . ? C11 C12 C13 C18 178.8(5) . . . . ? C11 C12 C13 C14 57.7(7) . . . . ? O27 C13 C14 O28 175.8(4) . . . . ? C18 C13 C14 O28 -65.1(6) . . . . ? C12 C13 C14 O28 56.5(6) . . . . ? O27 C13 C14 C15 -65.0(6) . . . . ? C18 C13 C14 C15 54.0(6) . . . . ? C12 C13 C14 C15 175.7(5) . . . . ? O27 C13 C14 C8 59.1(6) . . . . ? C18 C13 C14 C8 178.2(5) . . . . ? C12 C13 C14 C8 -60.2(6) . . . . ? C7 C8 C14 O28 70.0(7) . . . . ? C9 C8 C14 O28 -55.3(7) . . . . ? C7 C8 C14 C15 -53.8(7) . . . . ? C9 C8 C14 C15 -179.0(5) . . . . ? C7 C8 C14 C13 -175.4(5) . . . . ? C9 C8 C14 C13 59.4(6) . . . . ? O28 C14 C15 C16 56.5(8) . . . . ? C13 C14 C15 C16 -58.4(7) . . . . ? C8 C14 C15 C16 178.4(5) . . . . ? C14 C15 C16 C17 59.4(8) . . . . ? C15 C16 C17 C18 -50.4(7) . . . . ? C15 C16 C17 C20 74.9(8) . . . . ? O27 C13 C18 C17 61.8(8) . . . . ? C14 C13 C18 C17 -53.1(7) . . . . ? C12 C13 C18 C17 -173.0(5) . . . . ? C16 C17 C18 C13 50.0(7) . . . . ? C20 C17 C18 C13 -75.5(7) . . . . ? C16 C17 C20 O26 177.2(5) . . . . ? C18 C17 C20 O26 -60.5(6) . . . . ? C16 C17 C20 C21 59.7(7) . . . . ? C18 C17 C20 C21 -178.1(6) . . . . ? O25 C22 O26 C20 3.1(9) . . . . ? C23 C22 O26 C20 -177.9(6) . . . . ? C21 C20 O26 C22 -80.4(7) . . . . ? C17 C20 O26 C22 159.8(5) . . . . ? C18 C13 O27 C24 72.3(7) . . . . ? C14 C13 O27 C24 -169.1(5) . . . . ? C12 C13 O27 C24 -52.3(7) . . . . ? 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 O28 H28 O29 0.86(.03) 2.180(.046) 2.80(.01) 129.(3.) 4_476 # Symmetry code: 4_476 x-1/2,-y+1/2+2,-z+1 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.186 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.047 #===END data_20R-iodo _database_code_CSD 161561 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (20R)-20-iodo-4-pregnen-3-one ; _chemical_formula_moiety 'C21 H31 I O' _chemical_formula_sum 'C21 H31 I O' _chemical_formula_weight 426.36 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' 'O' '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 'P 21 21 21' 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 7.887(3) _cell_length_b 12.510(2) _cell_length_c 20.083(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1981.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 12.5 _exptl_crystal_description prisms _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.620 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.69 _exptl_absorpt_correction_T_max 0.76 _diffrn_ambient_temperature 293(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 'Siemens R3m' _diffrn_measurement_method \w/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_decay_% <2 _diffrn_reflns_number 9154 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.48 _reflns_number_total 2681 _reflns_number_gt 2312 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/P4-PC version V4.27 (1991)' _computing_cell_refinement 'Siemens P3/P4-PC version V4.27 (1991)' _computing_data_reduction 'XDISK in SHELXTL/PC(Sheldrick,1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC(Sheldrick,1994)' _computing_publication_material ; PARST (Nardelli, 1983) and CSD (Allen, Kennard & Taylor, 1993) ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+1.2345P] 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 riding _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 2681 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max <0.001 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3873(9) 1.0384(4) 0.1615(4) 0.080(2) Uani 1 d . . . H1A H 0.3805 1.0466 0.1136 0.095 Uiso 1 calc R . . H1B H 0.4958 1.0058 0.1718 0.095 Uiso 1 calc R . . C2 C 0.3800(11) 1.1505(5) 0.1942(4) 0.095(3) Uani 1 d . . . H2A H 0.4033 1.1441 0.2414 0.114 Uiso 1 calc R . . H2B H 0.4666 1.1959 0.1747 0.114 Uiso 1 calc R . . C3 C 0.2101(11) 1.2009(4) 0.1845(3) 0.076(2) Uani 1 d . . . C4 C 0.0679(11) 1.1294(4) 0.1794(2) 0.0664(16) Uani 1 d . . . H4A H -0.0386 1.1601 0.1740 0.080 Uiso 1 calc R . . C5 C 0.0757(10) 1.0219(4) 0.1817(2) 0.0522(13) Uani 1 d . . . C6 C -0.0778(8) 0.9550(4) 0.1841(3) 0.0652(14) Uani 1 d . . . H6A H -0.1757 0.9996 0.1749 0.078 Uiso 1 calc R . . H6B H -0.0906 0.9267 0.2288 0.078 Uiso 1 calc R . . C7 C -0.0760(8) 0.8623(4) 0.1350(3) 0.0592(13) Uani 1 d . . . H7A H -0.0792 0.8897 0.0898 0.071 Uiso 1 calc R . . H7B H -0.1754 0.8180 0.1418 0.071 Uiso 1 calc R . . C8 C 0.0842(7) 0.7952(3) 0.1448(2) 0.0420(11) Uani 1 d . . . H8A H 0.0844 0.7658 0.1900 0.050 Uiso 1 calc R . . C9 C 0.2409(6) 0.8659(3) 0.1357(2) 0.0402(11) Uani 1 d . . . H9A H 0.2323 0.8960 0.0907 0.048 Uiso 1 calc R . . C10 C 0.2456(7) 0.9635(4) 0.1845(3) 0.0485(12) Uani 1 d . . . C11 C 0.4052(7) 0.8004(3) 0.1368(3) 0.0544(13) Uani 1 d . . . H11A H 0.4249 0.7752 0.1818 0.065 Uiso 1 calc R . . H11B H 0.4991 0.8467 0.1248 0.065 Uiso 1 calc R . . C12 C 0.4033(7) 0.7027(3) 0.0889(2) 0.0483(12) Uani 1 d . . . H12A H 0.4017 0.7276 0.0431 0.058 Uiso 1 calc R . . H12B H 0.5056 0.6608 0.0953 0.058 Uiso 1 calc R . . C13 C 0.2486(6) 0.6328(3) 0.1017(2) 0.0374(11) Uani 1 d . . . C14 C 0.0920(6) 0.7038(3) 0.0950(2) 0.0420(11) Uani 1 d . . . H14A H 0.0997 0.7371 0.0510 0.050 Uiso 1 calc R . . C15 C -0.0576(8) 0.6269(4) 0.0916(3) 0.0601(14) Uani 1 d . . . H15A H -0.1519 0.6585 0.0676 0.072 Uiso 1 calc R . . H15B H -0.0953 0.6069 0.1359 0.072 Uiso 1 calc R . . C16 C 0.0138(7) 0.5305(4) 0.0542(3) 0.0648(16) Uani 1 d . . . H16A H -0.0384 0.5249 0.0106 0.078 Uiso 1 calc R . . H16B H -0.0096 0.4654 0.0787 0.078 Uiso 1 calc R . . C17 C 0.2094(6) 0.5468(4) 0.0469(2) 0.0473(11) Uani 1 d . . . H17A H 0.2312 0.5790 0.0033 0.057 Uiso 1 calc R . . C18 C 0.2602(9) 0.5782(4) 0.1692(2) 0.0582(15) Uani 1 d . . . H18A H 0.2547 0.6310 0.2038 0.087 Uiso 1 calc R . . H18B H 0.3655 0.5401 0.1723 0.087 Uiso 1 calc R . . H18C H 0.1676 0.5290 0.1741 0.087 Uiso 1 calc R . . C19 C 0.2736(9) 0.9277(4) 0.2574(3) 0.078(2) Uani 1 d . . . H19A H 0.2619 0.9881 0.2864 0.117 Uiso 1 calc R . . H19B H 0.3854 0.8981 0.2619 0.117 Uiso 1 calc R . . H19C H 0.1910 0.8745 0.2690 0.117 Uiso 1 calc R . . C20 C 0.2931(8) 0.4379(4) 0.0484(3) 0.0636(15) Uani 1 d . . . H20A H 0.2628 0.4029 0.0903 0.076 Uiso 1 calc R . . C21 C 0.2390(9) 0.3634(5) -0.0100(4) 0.095(2) Uani 1 d . . . H21B H 0.1194 0.3497 -0.0074 0.143 Uiso 1 calc R . . H21C H 0.2997 0.2970 -0.0070 0.143 Uiso 1 calc R . . H21D H 0.2645 0.3974 -0.0517 0.143 Uiso 1 calc R . . O22 O 0.1932(9) 1.2973(3) 0.1852(3) 0.113(2) Uani 1 d . . . I23 I 0.56918(6) 0.44506(3) 0.04187(2) 0.07375(16) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.070(5) 0.048(3) 0.120(5) -0.030(3) 0.001(4) -0.003(3) C2 0.099(6) 0.048(3) 0.139(6) -0.027(3) 0.005(5) -0.019(4) C3 0.114(6) 0.041(3) 0.074(4) -0.004(2) 0.022(4) 0.000(4) C4 0.085(5) 0.055(3) 0.059(3) 0.004(2) 0.009(4) 0.024(4) C5 0.064(4) 0.050(2) 0.042(2) -0.0081(18) 0.001(4) 0.009(3) C6 0.053(3) 0.062(3) 0.081(4) -0.013(3) 0.013(4) 0.019(4) C7 0.037(3) 0.063(3) 0.077(3) -0.018(3) -0.004(4) 0.004(3) C8 0.039(3) 0.043(2) 0.045(2) -0.0022(17) 0.005(3) -0.002(3) C9 0.034(3) 0.037(2) 0.050(3) -0.0040(19) -0.001(3) 0.000(2) C10 0.046(3) 0.040(2) 0.060(3) -0.009(2) -0.007(3) -0.001(3) C11 0.035(3) 0.041(2) 0.087(3) -0.009(2) -0.006(3) -0.004(3) C12 0.038(3) 0.040(2) 0.067(3) -0.008(2) -0.002(3) 0.002(2) C13 0.037(3) 0.035(2) 0.040(2) -0.0049(17) 0.002(2) -0.006(2) C14 0.034(3) 0.050(2) 0.042(2) -0.0044(18) 0.001(2) -0.009(3) C15 0.041(3) 0.064(3) 0.075(3) -0.016(2) 0.008(3) -0.013(3) C16 0.043(3) 0.069(3) 0.082(4) -0.024(3) 0.002(3) -0.020(3) C17 0.046(3) 0.046(2) 0.050(3) -0.008(2) 0.003(3) -0.005(3) C18 0.075(4) 0.050(3) 0.050(3) 0.002(2) -0.002(3) 0.000(3) C19 0.102(5) 0.068(3) 0.065(3) -0.022(3) -0.032(4) 0.020(4) C20 0.064(4) 0.047(2) 0.080(4) -0.027(3) 0.023(4) -0.011(3) C21 0.070(5) 0.085(4) 0.131(6) -0.056(4) -0.002(5) -0.016(4) O22 0.168(6) 0.0415(19) 0.129(4) 0.002(2) 0.042(4) 0.004(3) I23 0.0600(2) 0.05939(19) 0.1019(3) -0.0176(2) 0.0047(3) 0.0094(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C10 1.529(9) . ? C1 C2 1.550(7) . ? C2 C3 1.493(11) . ? C3 O22 1.213(6) . ? C3 C4 1.438(11) . ? C4 C5 1.347(7) . ? C5 C6 1.472(9) . ? C5 C10 1.527(9) . ? C6 C7 1.522(7) . ? C7 C8 1.530(8) . ? C8 C14 1.520(5) . ? C8 C9 1.531(7) . ? C9 C11 1.534(7) . ? C9 C10 1.566(6) . ? C10 C19 1.547(7) . ? C11 C12 1.556(6) . ? C12 C13 1.523(7) . ? C13 C14 1.527(7) . ? C13 C18 1.521(6) . ? C13 C17 1.570(6) . ? C14 C15 1.523(7) . ? C15 C16 1.528(7) . ? C16 C17 1.563(8) . ? C17 C20 1.513(7) . ? C20 C21 1.558(8) . ? C20 I23 2.183(6) . ? 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 C10 C1 C2 113.6(6) . . ? C3 C2 C1 111.1(6) . . ? O22 C3 C4 122.2(8) . . ? O22 C3 C2 121.1(7) . . ? C4 C3 C2 116.6(5) . . ? C5 C4 C3 125.6(8) . . ? C4 C5 C6 122.1(7) . . ? C4 C5 C10 121.2(7) . . ? C6 C5 C10 116.7(4) . . ? C5 C6 C7 113.9(5) . . ? C6 C7 C8 110.0(5) . . ? C14 C8 C9 108.9(4) . . ? C14 C8 C7 111.2(4) . . ? C9 C8 C7 109.5(3) . . ? C8 C9 C11 111.8(3) . . ? C8 C9 C10 113.2(4) . . ? C11 C9 C10 112.8(4) . . ? C5 C10 C1 109.7(4) . . ? C5 C10 C19 107.3(4) . . ? C1 C10 C19 111.0(5) . . ? C5 C10 C9 109.3(4) . . ? C1 C10 C9 107.8(4) . . ? C19 C10 C9 111.7(4) . . ? C9 C11 C12 113.7(4) . . ? C13 C12 C11 110.8(4) . . ? C14 C13 C18 112.8(4) . . ? C14 C13 C12 107.4(3) . . ? C18 C13 C12 111.1(4) . . ? C14 C13 C17 100.2(4) . . ? C18 C13 C17 109.2(4) . . ? C12 C13 C17 115.6(4) . . ? C8 C14 C13 114.3(4) . . ? C8 C14 C15 118.2(4) . . ? C13 C14 C15 105.3(4) . . ? C14 C15 C16 103.6(4) . . ? C15 C16 C17 107.9(4) . . ? C20 C17 C16 108.2(4) . . ? C20 C17 C13 121.2(4) . . ? C16 C17 C13 102.6(4) . . ? C17 C20 C21 113.9(5) . . ? C17 C20 I23 113.4(3) . . ? C21 C20 I23 104.6(4) . . ? 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 -54.1(8) . . . . ? C1 C2 C3 O22 -154.8(6) . . . . ? C1 C2 C3 C4 29.7(8) . . . . ? O22 C3 C4 C5 -176.4(6) . . . . ? C2 C3 C4 C5 -0.9(8) . . . . ? C3 C4 C5 C6 172.6(5) . . . . ? C3 C4 C5 C10 -5.3(8) . . . . ? C4 C5 C6 C7 132.5(5) . . . . ? C10 C5 C6 C7 -49.5(6) . . . . ? C5 C6 C7 C8 54.3(6) . . . . ? C6 C7 C8 C14 -178.3(4) . . . . ? C6 C7 C8 C9 -58.0(5) . . . . ? C14 C8 C9 C11 -51.6(5) . . . . ? C7 C8 C9 C11 -173.3(4) . . . . ? C14 C8 C9 C10 179.7(4) . . . . ? C7 C8 C9 C10 58.0(5) . . . . ? C4 C5 C10 C1 -18.3(6) . . . . ? C6 C5 C10 C1 163.6(5) . . . . ? C4 C5 C10 C19 102.4(6) . . . . ? C6 C5 C10 C19 -75.7(5) . . . . ? C4 C5 C10 C9 -136.4(5) . . . . ? C6 C5 C10 C9 45.6(5) . . . . ? C2 C1 C10 C5 47.3(7) . . . . ? C2 C1 C10 C19 -71.2(7) . . . . ? C2 C1 C10 C9 166.2(6) . . . . ? C8 C9 C10 C5 -50.0(5) . . . . ? C11 C9 C10 C5 -178.2(4) . . . . ? C8 C9 C10 C1 -169.2(4) . . . . ? C11 C9 C10 C1 62.5(5) . . . . ? C8 C9 C10 C19 68.6(6) . . . . ? C11 C9 C10 C19 -59.7(6) . . . . ? C8 C9 C11 C12 50.8(6) . . . . ? C10 C9 C11 C12 179.8(4) . . . . ? C9 C11 C12 C13 -53.4(5) . . . . ? C11 C12 C13 C14 55.9(5) . . . . ? C11 C12 C13 C18 -68.0(5) . . . . ? C11 C12 C13 C17 166.8(4) . . . . ? C9 C8 C14 C13 59.4(5) . . . . ? C7 C8 C14 C13 -179.9(4) . . . . ? C9 C8 C14 C15 -175.8(4) . . . . ? C7 C8 C14 C15 -55.1(6) . . . . ? C18 C13 C14 C8 61.1(5) . . . . ? C12 C13 C14 C8 -61.7(5) . . . . ? C17 C13 C14 C8 177.1(4) . . . . ? C18 C13 C14 C15 -70.3(5) . . . . ? C12 C13 C14 C15 166.9(4) . . . . ? C17 C13 C14 C15 45.7(4) . . . . ? C8 C14 C15 C16 -163.4(4) . . . . ? C13 C14 C15 C16 -34.2(5) . . . . ? C14 C15 C16 C17 8.8(6) . . . . ? C15 C16 C17 C20 147.8(5) . . . . ? C15 C16 C17 C13 18.7(6) . . . . ? C14 C13 C17 C20 -158.9(4) . . . . ? C18 C13 C17 C20 -40.2(6) . . . . ? C12 C13 C17 C20 86.0(6) . . . . ? C14 C13 C17 C16 -38.3(5) . . . . ? C18 C13 C17 C16 80.4(5) . . . . ? C12 C13 C17 C16 -153.4(4) . . . . ? C16 C17 C20 C21 62.3(6) . . . . ? C13 C17 C20 C21 -179.9(5) . . . . ? C16 C17 C20 I23 -178.2(4) . . . . ? C13 C17 C20 I23 -60.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.411 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.060 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 C6 H6B O22 0.97(.01) 2.503(.005) 3.41(.01) 155.(0.) 3_545 C20 H20A O22 0.98(.01) 2.382(.005) 3.36(.01) 173.(0.) 1_545 # 3_545: -x,+y-1/2,-z+1/2 # 1_545: x,+y-1,+z #===END data_20S-iodo _database_code_CSD 161562 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (20S)-20-iodo-4-pregnen-3-one ; _chemical_formula_moiety 'C21 H31 I O' _chemical_formula_sum 'C21 H31 I O' _chemical_formula_weight 426.36 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 'P 21 21 21' 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 6.6963(19) _cell_length_b 11.819(3) _cell_length_c 24.686(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1953.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 12.5 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.643 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_T_max 0.82 _diffrn_ambient_temperature 293(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 'Siemens R3m' _diffrn_measurement_method \w/2\q _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_decay_% <2 _diffrn_reflns_number 2191 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2071 _reflns_number_gt 1198 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3/P4-PC version V4.27 (1991)' _computing_cell_refinement 'Siemens P3/P4-PC version V4.27 (1991)' _computing_data_reduction 'XDISK in SHELXTL/PC(Sheldrick,1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP in SHELXTL/PC(Sheldrick,1994)' _computing_publication_material ; PARST (Nardelli, 1983) and CSD (Allen, Kennard & Taylor, 1993) ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0922P)^2^+0.0000P] 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 riding _refine_ls_extinction_method none _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(8) _refine_ls_number_reflns 2071 _refine_ls_number_parameters 212 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.163 _refine_ls_shift/su_mean 0.030 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.4517(18) 0.4673(17) 0.5849(4) 0.092(5) Uani 1 d . . . H1D H 1.5313 0.5331 0.5941 0.110 Uiso 1 calc R . . H1E H 1.5358 0.4011 0.5892 0.110 Uiso 1 calc R . . C2 C 1.388(2) 0.4765(14) 0.5245(4) 0.096(5) Uani 1 d . . . H2B H 1.3202 0.5479 0.5186 0.115 Uiso 1 calc R . . H2C H 1.5060 0.4750 0.5016 0.115 Uiso 1 calc R . . C3 C 1.252(2) 0.3807(11) 0.5092(4) 0.082(5) Uani 1 d . . . C4 C 1.130(2) 0.3358(11) 0.5520(4) 0.079(4) Uani 1 d . . . H4C H 1.0402 0.2787 0.5430 0.095 Uiso 1 calc R . . C5 C 1.134(2) 0.3697(8) 0.6037(4) 0.059(3) Uani 1 d . . . C6 C 0.984(2) 0.3259(12) 0.6426(4) 0.080(4) Uani 1 d . . . H6B H 0.8846 0.3840 0.6487 0.095 Uiso 1 calc R . . H6C H 0.9175 0.2614 0.6265 0.095 Uiso 1 calc R . . C7 C 1.070(2) 0.2904(10) 0.6968(4) 0.069(4) Uani 1 d . . . H7B H 1.1524 0.2237 0.6920 0.083 Uiso 1 calc R . . H7C H 0.9617 0.2710 0.7212 0.083 Uiso 1 calc R . . C8 C 1.1947(15) 0.3850(8) 0.7216(4) 0.047(3) Uani 1 d . . . H8C H 1.1066 0.4497 0.7283 0.057 Uiso 1 calc R . . C9 C 1.3571(16) 0.4223(8) 0.6818(4) 0.051(3) Uani 1 d . . . H9C H 1.4402 0.3554 0.6754 0.061 Uiso 1 calc R . . C10 C 1.2770(15) 0.4588(8) 0.6249(4) 0.049(3) Uani 1 d . . . C11 C 1.4962(19) 0.5114(10) 0.7068(4) 0.066(4) Uani 1 d . . . H11B H 1.6065 0.5250 0.6821 0.079 Uiso 1 calc R . . H11C H 1.4233 0.5818 0.7108 0.079 Uiso 1 calc R . . C12 C 1.5808(16) 0.4762(12) 0.7625(4) 0.064(4) Uani 1 d . . . H12A H 1.6586 0.5381 0.7774 0.077 Uiso 1 calc R . . H12B H 1.6689 0.4118 0.7580 0.077 Uiso 1 calc R . . C13 C 1.4135(14) 0.4454(8) 0.8020(4) 0.050(3) Uani 1 d . . . C14 C 1.2905(16) 0.3518(9) 0.7746(4) 0.054(3) Uani 1 d . . . H14C H 1.3851 0.2912 0.7660 0.065 Uiso 1 calc R . . C15 C 1.157(2) 0.3057(12) 0.8193(4) 0.079(4) Uani 1 d . . . H15A H 1.0353 0.3497 0.8223 0.095 Uiso 1 calc R . . H15B H 1.1227 0.2273 0.8126 0.095 Uiso 1 calc R . . C16 C 1.2836(18) 0.3168(12) 0.8705(5) 0.072(4) Uani 1 d . . . H16B H 1.3187 0.2425 0.8842 0.087 Uiso 1 calc R . . H16C H 1.2096 0.3567 0.8983 0.087 Uiso 1 calc R . . C17 C 1.4761(17) 0.3841(8) 0.8552(4) 0.050(3) Uani 1 d . . . H17C H 1.5807 0.3293 0.8462 0.060 Uiso 1 calc R . . C18 C 1.289(2) 0.5498(10) 0.8161(5) 0.077(4) Uani 1 d . . . H18C H 1.3735 0.6056 0.8329 0.115 Uiso 1 calc R . . H18D H 1.1846 0.5289 0.8407 0.115 Uiso 1 calc R . . H18E H 1.2322 0.5807 0.7837 0.115 Uiso 1 calc R . . C19 C 1.161(2) 0.5717(9) 0.6283(5) 0.077(5) Uani 1 d . . . H19A H 1.0487 0.5630 0.6520 0.116 Uiso 1 calc R . . H19B H 1.1159 0.5927 0.5928 0.116 Uiso 1 calc R . . H19C H 1.2479 0.6296 0.6422 0.116 Uiso 1 calc R . . C20 C 1.5505(17) 0.4559(9) 0.9015(3) 0.063(4) Uani 1 d . . . H20D H 1.4393 0.5040 0.9133 0.075 Uiso 1 calc R . . C21 C 1.7294(18) 0.5337(11) 0.8905(5) 0.060(4) Uani 1 d . . . H21D H 1.6912 0.5914 0.8651 0.090 Uiso 1 calc R . . H21E H 1.8372 0.4901 0.8756 0.090 Uiso 1 calc R . . H21F H 1.7717 0.5683 0.9237 0.090 Uiso 1 calc R . . O22 O 1.2361(19) 0.3517(10) 0.4622(3) 0.110(4) Uani 1 d . . . I23 I 1.6281(2) 0.34502(9) 0.96964(4) 0.0998(5) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.082(12) 0.136(14) 0.058(8) -0.018(10) 0.003(8) -0.019(11) C2 0.097(11) 0.154(14) 0.037(7) 0.007(9) 0.042(9) -0.003(14) C3 0.093(12) 0.074(10) 0.080(11) -0.004(9) -0.020(10) 0.029(10) C4 0.101(11) 0.064(8) 0.072(8) -0.008(7) -0.016(10) 0.004(13) C5 0.069(8) 0.046(7) 0.061(7) -0.010(6) 0.000(8) -0.006(9) C6 0.080(10) 0.081(11) 0.077(9) -0.017(8) -0.013(9) -0.007(10) C7 0.061(10) 0.086(9) 0.061(8) 0.002(7) -0.004(7) -0.012(8) C8 0.046(8) 0.040(6) 0.056(7) -0.003(5) -0.006(6) 0.000(6) C9 0.047(7) 0.042(6) 0.064(7) -0.011(5) -0.012(7) 0.004(7) C10 0.048(7) 0.048(7) 0.052(7) -0.010(6) 0.010(6) 0.004(7) C11 0.054(8) 0.084(10) 0.060(7) 0.000(7) 0.001(7) -0.031(9) C12 0.053(9) 0.086(9) 0.055(7) -0.002(7) 0.016(6) -0.021(8) C13 0.045(8) 0.048(7) 0.056(7) -0.013(6) 0.008(6) -0.001(7) C14 0.059(8) 0.042(6) 0.062(7) -0.014(6) 0.000(6) -0.010(7) C15 0.068(10) 0.087(10) 0.083(9) 0.020(8) 0.004(9) -0.025(9) C16 0.080(11) 0.081(10) 0.055(7) 0.024(7) -0.003(7) -0.007(9) C17 0.063(9) 0.038(6) 0.049(6) -0.002(5) 0.011(6) 0.000(7) C18 0.100(12) 0.067(9) 0.064(8) 0.006(7) -0.014(8) 0.020(9) C19 0.106(13) 0.066(8) 0.060(8) 0.002(6) -0.003(9) 0.028(10) C20 0.074(10) 0.066(8) 0.048(7) 0.007(6) -0.011(7) 0.016(8) C21 0.058(8) 0.081(9) 0.043(6) -0.001(7) -0.002(6) -0.019(9) O22 0.147(10) 0.131(9) 0.052(6) -0.034(6) -0.022(6) 0.059(9) I23 0.1350(10) 0.0899(7) 0.0744(6) 0.0130(6) -0.0193(8) -0.0005(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.555(9) . ? C1 C10 1.535(9) . ? C2 C3 1.502(9) . ? C3 O22 1.215(9) . ? C3 C4 1.438(9) . ? C4 C5 1.339(9) . ? C5 C10 1.515(9) . ? C5 C6 1.483(9) . ? C6 C7 1.514(9) . ? C7 C8 1.524(9) . ? C8 C14 1.510(9) . ? C8 C9 1.531(9) . ? C9 C11 1.535(9) . ? C9 C10 1.563(9) . ? C10 C19 1.545(9) . ? C11 C12 1.545(9) . ? C12 C13 1.530(9) . ? C13 C17 1.556(9) . ? C13 C18 1.528(9) . ? C13 C14 1.536(9) . ? C14 C15 1.520(9) . ? C15 C16 1.525(9) . ? C16 C17 1.561(9) . ? C17 C20 1.509(9) . ? C20 C21 1.534(9) . ? C20 I23 2.195(8) . ? 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 114.4(10) . . ? C3 C2 C1 110.8(11) . . ? O22 C3 C4 123.2(12) . . ? O22 C3 C2 120.4(13) . . ? C4 C3 C2 116.0(10) . . ? C5 C4 C3 125.3(12) . . ? C4 C5 C10 123.5(11) . . ? C4 C5 C6 119.9(11) . . ? C10 C5 C6 116.5(9) . . ? C7 C6 C5 114.4(11) . . ? C6 C7 C8 111.0(10) . . ? C14 C8 C7 113.0(8) . . ? C14 C8 C9 109.2(8) . . ? C7 C8 C9 110.1(8) . . ? C11 C9 C10 112.4(8) . . ? C11 C9 C8 111.8(8) . . ? C10 C9 C8 114.3(8) . . ? C5 C10 C19 107.7(9) . . ? C5 C10 C9 109.6(8) . . ? C19 C10 C9 111.2(8) . . ? C5 C10 C1 107.7(10) . . ? C19 C10 C1 111.1(11) . . ? C9 C10 C1 109.5(8) . . ? C12 C11 C9 113.3(9) . . ? C11 C12 C13 111.3(9) . . ? C17 C13 C12 116.8(8) . . ? C17 C13 C18 109.3(8) . . ? C12 C13 C18 110.5(9) . . ? C17 C13 C14 100.4(7) . . ? C12 C13 C14 106.5(8) . . ? C18 C13 C14 113.0(9) . . ? C8 C14 C15 118.2(9) . . ? C8 C14 C13 115.0(8) . . ? C15 C14 C13 104.7(8) . . ? C16 C15 C14 104.1(9) . . ? C15 C16 C17 107.6(9) . . ? C20 C17 C13 117.8(7) . . ? C20 C17 C16 112.1(9) . . ? C13 C17 C16 102.6(8) . . ? C21 C20 C17 117.4(9) . . ? C21 C20 I23 108.0(7) . . ? C17 C20 I23 108.9(6) . . ? 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 -54.3(19) . . . . ? C1 C2 C3 O22 -156.8(14) . . . . ? C1 C2 C3 C4 29.6(19) . . . . ? O22 C3 C4 C5 -176.1(14) . . . . ? C2 C3 C4 C5 -3(2) . . . . ? C3 C4 C5 C10 -2(2) . . . . ? C3 C4 C5 C6 173.0(13) . . . . ? C4 C5 C6 C7 135.4(13) . . . . ? C10 C5 C6 C7 -49.0(16) . . . . ? C5 C6 C7 C8 52.7(15) . . . . ? C6 C7 C8 C14 -177.6(10) . . . . ? C6 C7 C8 C9 -55.1(13) . . . . ? C14 C8 C9 C11 -51.1(11) . . . . ? C7 C8 C9 C11 -175.7(10) . . . . ? C14 C8 C9 C10 179.9(8) . . . . ? C7 C8 C9 C10 55.2(11) . . . . ? C4 C5 C10 C19 99.5(14) . . . . ? C6 C5 C10 C19 -75.9(13) . . . . ? C4 C5 C10 C9 -139.5(13) . . . . ? C6 C5 C10 C9 45.2(13) . . . . ? C4 C5 C10 C1 -20.4(17) . . . . ? C6 C5 C10 C1 164.2(11) . . . . ? C11 C9 C10 C5 -177.6(10) . . . . ? C8 C9 C10 C5 -48.9(11) . . . . ? C11 C9 C10 C19 -58.7(13) . . . . ? C8 C9 C10 C19 70.0(11) . . . . ? C11 C9 C10 C1 64.4(13) . . . . ? C8 C9 C10 C1 -166.8(11) . . . . ? C2 C1 C10 C5 47.9(17) . . . . ? C2 C1 C10 C19 -69.7(17) . . . . ? C2 C1 C10 C9 167.1(12) . . . . ? C10 C9 C11 C12 -178.9(10) . . . . ? C8 C9 C11 C12 51.1(14) . . . . ? C9 C11 C12 C13 -54.6(15) . . . . ? C11 C12 C13 C17 167.2(9) . . . . ? C11 C12 C13 C18 -67.0(13) . . . . ? C11 C12 C13 C14 56.1(12) . . . . ? C7 C8 C14 C15 -53.9(14) . . . . ? C9 C8 C14 C15 -176.8(10) . . . . ? C7 C8 C14 C13 -178.4(10) . . . . ? C9 C8 C14 C13 58.6(11) . . . . ? C17 C13 C14 C8 177.0(9) . . . . ? C12 C13 C14 C8 -60.8(12) . . . . ? C18 C13 C14 C8 60.7(12) . . . . ? C17 C13 C14 C15 45.5(11) . . . . ? C12 C13 C14 C15 167.7(10) . . . . ? C18 C13 C14 C15 -70.7(12) . . . . ? C8 C14 C15 C16 -162.7(10) . . . . ? C13 C14 C15 C16 -33.1(14) . . . . ? C14 C15 C16 C17 7.5(15) . . . . ? C12 C13 C17 C20 82.5(13) . . . . ? C18 C13 C17 C20 -43.9(14) . . . . ? C14 C13 C17 C20 -162.9(10) . . . . ? C12 C13 C17 C16 -153.9(10) . . . . ? C18 C13 C17 C16 79.7(11) . . . . ? C14 C13 C17 C16 -39.3(10) . . . . ? C15 C16 C17 C20 147.6(11) . . . . ? C15 C16 C17 C13 20.2(13) . . . . ? C13 C17 C20 C21 -56.5(14) . . . . ? C16 C17 C20 C21 -175.3(10) . . . . ? C13 C17 C20 I23 -179.6(7) . . . . ? C16 C17 C20 I23 61.7(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.375 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.139 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 C4 H4C O22 0.93(.01) 2.557(.013) 3.46(.02) 164.(1.) 4_456 C20 H20D O22 0.98(.01) 2.397(.012) 3.33(.02) 159.(1.) 2_765 # 4_456: x-1/2,-y+1/2,-z+1 # 2_765: -x+1/2+2,-y+1,+z+1/2 #===END