data_1100689 _journal_name_full 'Analytical Sciences' _journal_year 2003 _journal_volume 19 _journal_page_first x79 _journal_page_last x80 _publ_section_title ; Crystal structure and Synthesis of beta-(p-Fluorobenzoyloxy)-4,16-pregnadiene- 6,20-dione ; loop_ _publ_author_name 'Soriano-Garcia, Manuel' 'Valencia, Norma' 'Flores, Eugenio' 'Bratoeff, Eugene' 'Ramirez, Elena' 'Cabeza, Marisa' _chemical_name_systematic ; Crystal structure and Synthesis of beta-(p-Fluorobenzoyloxy)-4,16-pregnadiene- 6,20-dione ; _chemical_name_systematic _chemical_formula_moiety 'C28 H31 F O4' _chemical_formula_sum 'C28 H31 F O4' _chemical_formula_weight 450.53 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.4629(10) _cell_length_b 6.1705(5) _cell_length_c 15.5815(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.243(2) _cell_angle_gamma 90.00 _cell_volume 1171.00(17) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3041 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.91 _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas No _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 291(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 CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% ? _diffrn_reflns_number 9645 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0742 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4105 _reflns_number_gt 2458 _reflns_threshold_expression >2sigma(I) _solved_by 'Simon Hernandez-Ortega _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^)+(0.0255P)^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 mixed _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 0.0(12) _refine_ls_number_reflns 4105 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.911 _refine_ls_shift/su_max 0.002 _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 F1 F 0.89588(16) -0.2856(4) 0.93806(15) 0.1216(9) Uani 1 1 d . . . O1 O 0.47275(15) 0.2761(4) 0.85507(13) 0.0760(7) Uani 1 1 d . . . O2 O 0.11870(16) -0.0393(4) 0.86268(14) 0.0790(7) Uani 1 1 d . . . O3 O 0.55700(17) 0.4447(4) 0.97741(16) 0.0895(8) Uani 1 1 d . . . O4 O -0.35254(19) 0.8746(4) 0.51195(17) 0.0998(9) Uani 1 1 d . . . C1 C 0.2393(2) 0.6067(5) 0.7320(2) 0.0658(10) Uani 1 1 d . .. . H1A H 0.2260 0.7092 0.7758 0.079 Uiso 1 1 calc R . . H1B H 0.2298 0.6829 0.6765 0.079 Uiso 1 1 calc R . . C2 C 0.3579(2) 0.5249(6) 0.7583(2) 0.0707(10) Uani 1 1 d . . . H2A H 0.3726 0.4247 0.7142 0.085 Uiso 1 1 calc R . . H2B H 0.4083 0.6460 0.7617 0.085 Uiso 1 1 calc R . .. C3 C 0.3753(2) 0.4127(6) 0.8462(2) 0.0676(10) Uani 1 1 d . . . H3 H 0.3876 0.5217 0.8930 0.081 Uiso 1 1 calc R . . C4 C 0.2824(2) 0.2735(6) 0.85550(19) 0.0665(10) Uani 1 1 d . . . H4 H 0.2941 0.1744 0.9015 0.080 Uiso 1 1 calc R . . C5 C 0.0962(3) 0.1368(5) 0.82529(19) 0.0538(8) Uani 1 1 d . . . C6 C -0.0186(2) 0.2159(5) 0.80490(17) 0.0523(8) Uani 1 1 d . . . H6A H -0.0301 0.3095 0.8522 0.063 Uiso 1 1 calc R . . H6B H -0.0678 0.0930 0.8022 0.063 Uiso 1 1 calc R . . C7 C -0.0479(2) 0.3402(5) 0.71859(17) 0.0438(7) Uani 1 1 d . . . H7 H -0.0486 0.2387 0.6701 0.053 Uiso 1 1 calc R . . C8 C 0.0368(2) 0.5170(5) 0.71485(18) 0.0441(7) Uani 1 1 d . . . H8 H 0.0396 0.6057 0.7674 0.053 Uiso 1 1 calc R . . C9 C 0.1549(2) 0.4247(5) 0.72332(18) 0.0454(7) Uani 1 1 d . . . C10 C 0.1834(2) 0.2785(5) 0.80326(18) 0.0493(8) Uani 1 1 d . . . C11 C 0.0019(2) 0.6724(5) 0.63654(19) 0.0582(9) Uani 1 1 d . . . H11A H 0.0512 0.7960 0.6449 0.070 Uiso 1 1 calc R .. . H11B H 0.0106 0.5986 0.5835 0.070 Uiso 1 1 calc R . . C12 C -0.1164(2) 0.7555(5) 0.62308(19) 0.0585(9) Uani 1 1 d . . . H12A H -0.1225 0.8535 0.6705 0.070 Uiso 1 1 calc R . . H12B H -0.1349 0.8353 0.5683 0.070 Uiso 1 1 calc R . . C13 C -0.1961(2) 0.5684(4) 0.62092(18) 0.0437(7) Uani 1 1 d . . . C14 C -0.1607(2) 0.4427(5) 0.70715(17) 0.0443(7) Uani 1 1 d . . . H14 H -0.1531 0.5527 0.7534 0.053 Uiso 1 1 calc R . . C15 C -0.2640(2) 0.3117(6) 0.71456(19) 0.0609(9) Uani 1 1 d . . . H15A H -0.2693 0.1778 0.6813 0.073 Uiso 1 1 calc R . . H15B H -0.2656 0.2795 0.7752 0.073 Uiso 1 1 calc R . . C16 C -0.3518(2) 0.4684(6) 0.67502(19) 0.0614(9) Uani 1 1 d . .. . H16 H -0.4232 0.4641 0.6840 0.074 Uiso 1 1 calc R . . C17 C -0.3151(2) 0.6164(5) 0.6249(2) 0.0532(8) Uani 1 1 d . . . C18 C -0.1999(2) 0.4263(5) 0.53894(17) 0.0619(9) Uani 1 1 d . . . H18A H -0.1265 0.3863 0.5353 0.074 Uiso 1 1 calc R .. . H18B H -0.2334 0.5062 0.4873 0.074 Uiso 1 1 calc R . . H18C H -0.2420 0.2980 0.5431 0.074 Uiso 1 1 calc R . . C19 C 0.1606(2) 0.2852(5) 0.64282(17) 0.0636(9) Uani 1 1 d . . . H19A H 0.2320 0.2204 0.6505 0.076 Uiso 1 1 calc R .. . H19B H 0.1474 0.3745 0.5912 0.076 Uiso 1 1 calc R . . H19C H 0.1059 0.1735 0.6364 0.076 Uiso 1 1 calc R . . C20 C -0.3827(3) 0.7843(6) 0.5708(2) 0.0640(9) Uani 1 1 d . . . C21 C -0.4921(2) 0.8383(6) 0.5906(2) 0.0954(13) Uani 1 1 d . .. . H21A H -0.4826 0.8788 0.6513 0.114 Uiso 1 1 calc R . . H21B H -0.5393 0.7141 0.5792 0.114 Uiso 1 1 calc R . . H21C H -0.5244 0.9566 0.5541 0.114 Uiso 1 1 calc R . . C22 C 0.5541(2) 0.3037(6) 0.9236(2) 0.0584(9) Uani 1 1 d . .. . C23 C 0.6445(2) 0.1450(6) 0.92648(19) 0.0504(8) Uani 1 1 d . . . C24 C 0.7465(3) 0.1907(6) 0.97516(19) 0.0632(9) Uani 1 1 d . . . H24 H 0.7585 0.3203 1.0062 0.076 Uiso 1 1 calc R . . C25 C 0.8323(3) 0.0457(8) 0.9787(2) 0.0800(12) Uani 1 1 d . . . H25 H 0.9020 0.0772 1.0114 0.096 Uiso 1 1 calc R . . C26 C 0.8122(3) -0.1426(7) 0.9337(3) 0.0745(11) Uani 1 1 d . . . C27 C 0.7130(3) -0.1965(6) 0.8856(2) 0.0775(10) Uani 1 1 d . .. . H27 H 0.7019 -0.3284 0.8562 0.093 Uiso 1 1 calc R . . C28 C 0.6279(3) -0.0495(7) 0.8811(2) 0.0687(10) Uani 1 1 d . . . H28 H 0.5588 -0.0817 0.8473 0.082 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 F1 0.0798(14) 0.134(2) 0.157(2) 0.0349(18) 0.0392(14) 0.0445(15) O1 0.0461(13) 0.109(2) 0.0678(14) -0.0186(16) 0.0010(11) 0.0104(14) O2 0.0752(16) 0.0749(19) 0.0853(17) 0.0228(16) 0.0131(13) 0.0091(15) O3 0.0664(15) 0.094(2) 0.1009(19) -0.0428(18) 0.0023(13) 0.0030(15) O4 0.0761(18) 0.103(2) 0.115(2) 0.0533(19) 0.0072(15) 0.0122(15) C1 0.051(2) 0.065(2) 0.081(2) 0.001(2) 0.0134(18) -0.0033(19) C2 0.0449(19) 0.080(3) 0.086(3) 0.002(2) 0.0124(18) -0.0040(19) C3 0.0417(19) 0.093(3) 0.068(2) -0.012(2) 0.0111(17) 0.009(2) C4 0.059(2) 0.089(3) 0.0527(19) 0.003(2) 0.0143(17) 0.014(2) C5 0.065(2) 0.052(2) 0.0433(19) 0.0079(17) 0.0086(16) 0.0125(19) C6 0.0519(19) 0.057(2) 0.0513(19) 0.0072(17) 0.0176(15) 0.0043(16) C7 0.0467(17) 0.0461(19) 0.0390(16) 0.0022(14) 0.0101(13) 0.0042(15) C8 0.0419(17) 0.0380(18) 0.0516(19) -0.0026(15) 0.0081(14) -0.0034(15) C9 0.0494(18) 0.0437(18) 0.0454(18) -0.0038(17) 0.0149(14) -0.0029(16) C10 0.0467(18) 0.058(2) 0.0438(18) -0.0010(17) 0.0105(15) 0.0136(18) C11 0.0505(19) 0.050(2) 0.070(2) 0.0157(18) 0.0033(16) -0.0105(16) C12 0.055(2) 0.047(2) 0.068(2) 0.0087(18) -0.0003(16) -0.0049(18) C13 0.0463(18) 0.0371(17) 0.0438(18) 0.0022(15) 0.0011(14) -0.0029(15) C14 0.0467(17) 0.0429(19) 0.0426(17) -0.0007(16) 0.0085(14) -0.0013(16) C15 0.061(2) 0.061(2) 0.062(2) 0.015(2) 0.0172(16) 0.0004(19) C16 0.0388(17) 0.078(3) 0.069(2) 0.019(2) 0.0146(16) 0.0002(19) C17 0.0439(19) 0.052(2) 0.058(2) -0.0025(18) -0.0012(16) 0.0029(17) C18 0.062(2) 0.067(2) 0.0538(19) 0.0060(19) 0.0057(15) -0.0115(19) C19 0.065(2) 0.074(2) 0.0530(18) 0.002(2) 0.0153(15) 0.001(2) C20 0.056(2) 0.056(2) 0.076(2) 0.007(2) 0.0035(19) 0.002(2) C21 0.064(2) 0.089(3) 0.127(3) 0.024(3) 0.006(2) 0.020(2) C22 0.051(2) 0.069(2) 0.056(2) -0.011(2) 0.0124(17) -0.012(2) C23 0.0388(18) 0.059(2) 0.054(2) 0.0023(18) 0.0116(15) -0.0058(17) C24 0.050(2) 0.079(3) 0.059(2) 0.002(2) 0.0089(17) -0.013(2) C25 0.049(2) 0.118(4) 0.071(3) 0.017(3) 0.0058(19) -0.010(3) C26 0.050(2) 0.091(3) 0.088(3) 0.021(3) 0.028(2) 0.015(2) C27 0.069(2) 0.067(3) 0.098(3) -0.011(2) 0.022(2) 0.008(2) C28 0.053(2) 0.087(3) 0.064(2) -0.003(2) 0.0084(17) -0.014(2) _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 F1 C26 1.356(4) . y O1 C22 1.318(3) . y O1 C3 1.460(3) . y O2 C5 1.236(3) . y O3 C22 1.203(3) . y O4 C20 1.199(3) . y C1 C9 1.525(4) . y C1 C2 1.533(3) . y C2 C3 1.509(4) . y C3 C4 1.473(4) . y C4 C10 1.327(3) . y C5 C6 1.482(3) . y C5 C10 1.490(4) . y C6 C7 1.524(3) . y C7 C14 1.516(3) . y C7 C8 1.528(3) . y C8 C11 1.541(4) . y C8 C9 1.558(3) . y C9 C10 1.518(4) . y C9 C19 1.535(4) . y C11 C12 1.532(3) . y C12 C13 1.519(4) . y C13 C17 1.526(4) . y C13 C14 1.533(3) . y C13 C18 1.542(4) . y C14 C15 1.545(4) . y C15 C16 1.492(4) . y C16 C17 1.344(4) . y C17 C20 1.481(4) . y C20 C21 1.497(4) . y C22 C23 1.487(4) . y C23 C24 1.364(4) . y C23 C28 1.386(4) . y C24 C25 1.386(5) . y C25 C26 1.353(5) . y C26 C27 1.345(4) . y C27 C28 1.387(4) . y 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 C22 O1 C3 118.9(3) . . y C9 C1 C2 112.9(2) . . y C3 C2 C1 109.8(2) .. . y O1 C3 C4 108.0(3) . . y O1 C3 C2 107.9(2) . . y C4 C3 C2 113.1(3) . . y C10 C4 C3 125.0(3) . . y O2 C5 C6 120.2(3) .. . y O2 C5 C10 121.4(3) . . y C6 C5 C10 118.4(3) . . y C5 C6 C7 113.3(2) . . y C14 C7 C6 110.9(2) . . y C14 C7 C8 109.2(2) . . y C6 C7 C8 110.8(2) . . y C7 C8 C11 113.2(2) . . y C7 C8 C9 112.6(2) . .. y C11 C8 C9 113.4(2) . . y C10 C9 C1 109.1(2) . . y C10 C9 C19 107.1(2) . . y C1 C9 C19 109.6(2) . . y C10 C9 C8 109.8(2) .. . y C1 C9 C8 111.1(2) . . y C19 C9 C8 110.0(2) . . y C4 C10 C5 118.3(3) . . y C4 C10 C9 122.9(3) . . y C5 C10 C9 118.9(2) . . y C12 C11 C8 114.7(2) . . y C13 C12 C11 110.8(2) . . y C12 C13 C17 119.2(2) . . y C12 C13 C14 107.4(2) . . y C17 C13 C14 99.5(2) . . y C12 C13 C18 110.8(2) . . y C17 C13 C18 106.5(2) . . y C14 C13 C18 113.0(2) . . y C7 C14 C13 113.7(2) . . y C7 C14 C15 122.6(2) . . y C13 C14 C15 103.9(2) . . y C16 C15 C14 100.3(2) . . y C17 C16 C15 111.7(3) . . y C16 C17 C20 125.7(3) . . y C16 C17 C13 110.2(3) . . y C20 C17 C13 123.6(3) . . y O4 C20 C17 121.8(3) . . y O4 C20 C21 120.1(3) . . y C17 C20 C21 118.1(3) . . y O3 C22 O1 124.2(3) . . y O3 C22 C23 123.0(3) . . y O1 C22 C23 112.8(3) . . y C24 C23 C28 119.0(3) . . y C24 C23 C22 119.4(3) . . y C28 C23 C22 121.6(3) . . y C23 C24 C25 120.6(4) . . y C26 C25 C24 118.5(3) . . y C27 C26 C25 123.3(4) . . y C27 C26 F1 118.2(4) . . y C25 C26 F1 118.5(4) . . y C26 C27 C28 118.0(4) . . y C23 C28 C27 120.7(3) . . y _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.328 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.029