#------------------------------------------------------------------------------ #$Date: 2016-03-20 19:39:35 +0000 (Sun, 20 Mar 2016) $ #$Revision: 178373 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/00/4000030.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_4000030 loop_ _publ_author_name 'Bourgogne, Cyril' 'Fur, Yvette Le' 'Juen, Patrick' 'Masson, Patrick' 'Nicoud, Jean-Fran\,cois' 'Masse, Ren\'e' _publ_section_title ; Tetra(4-methoxyphenyl)phosphonium Iodide: A Twinned Crystal Built Up with Three-Dimensional Octupolar Nonlinear Optical Chromophores ; _journal_coden_ASTM CMATEX _journal_issue 4 _journal_name_full 'Chemistry of Materials' _journal_page_first 1025 _journal_page_last 1033 _journal_paper_doi 10.1021/cm991155c _journal_volume 12 _journal_year 2000 _chemical_formula_moiety '[(C7H7O)4 P1] I1' _chemical_formula_sum 'C28 H28 I O4 P' _chemical_formula_weight 586.41 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21 ' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.131(3) _cell_length_b 10.131(3) _cell_length_c 25.682(6) _cell_measurement_reflns_used 0 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 0.0 _cell_measurement_theta_min 0.0 _cell_volume 2635.9(9) _computing_cell_refinement 'Nonius Kappa CCD' _computing_data_collection 'Nonius Kappa CCD' _computing_data_reduction 'teXsan for Windows (MSC, 1997)' _computing_publication_material 'teXsan for Windows (MSC, 1997)' _computing_structure_refinement 'teXsan for Windows (MSC, 1997)' _computing_structure_solution 'SIR92 (Altomare, et. al. 1993)' _diffrn_ambient_temperature 296.2 _diffrn_measurement_device 'Nonius Kappa-CCD' _diffrn_measurement_method ? _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 _diffrn_radiation_detector 'CCD Camera' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-Ray fine focus' _diffrn_radiation_type 'Ag K\a' _diffrn_radiation_wavelength 0.5608 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.099 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 15346 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 19.26 _diffrn_reflns_theta_min 2.02 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.697 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_meas ? _exptl_crystal_description 'sqarred platelet' _exptl_crystal_F_000 1184.00 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.57 _refine_diff_density_min -0.48 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.163 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 307 _refine_ls_number_reflns 2189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0480 _refine_ls_shift/su_max 0.0000 _refine_ls_shift/su_mean 0.0000 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00002|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all 0.0320 _refine_ls_wR_factor_ref 0.0320 _reflns_number_gt 2189 _reflns_number_total 2550 _reflns_threshold_expression I>1.20\s(I) _cod_data_source_file cm991155c.cif _cod_data_source_block '_Template_texray.inf' _cod_original_formula_sum 'C28 H28 O4 P1 I1 ' _cod_database_code 4000030 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom I 0.68555(5) -0.37392(5) 0.60402(2) 0.0610(1) 1.000 . Uani d ? P 0.2798(1) 0.0582(2) 0.62621(6) 0.0318(4) 1.000 . Uani d ? O1 0.3844(5) 0.4500(4) 0.4607(2) 0.053(2) 1.000 . Uani d ? O2 0.6981(5) -0.0229(4) 0.7849(2) 0.0484(13) 1.000 . Uani d ? O3 0.1360(5) -0.4490(5) 0.5267(2) 0.059(2) 1.000 . Uani d ? O4 -0.1952(5) 0.2632(5) 0.7337(2) 0.053(1) 1.000 . Uani d ? C1 0.3218(6) 0.1655(5) 0.5738(2) 0.031(2) 1.000 . Uani d ? C2 0.4143(6) 0.2677(6) 0.5814(2) 0.038(2) 1.000 . Uani d ? C3 0.4317(6) 0.3619(7) 0.5419(3) 0.040(2) 1.000 . Uani d ? C4 0.3597(5) 0.3530(6) 0.4961(2) 0.034(2) 1.000 . Uani d ? C5 0.2745(6) 0.2508(7) 0.4881(2) 0.037(2) 1.000 . Uani d ? C6 0.2557(6) 0.1585(6) 0.5271(2) 0.038(2) 1.000 . Uani d ? C7 0.2940(8) 0.4696(8) 0.4197(3) 0.059(2) 1.000 . Uani d ? C11 0.4121(6) 0.0405(6) 0.6730(2) 0.034(2) 1.000 . Uani d ? C12 0.5105(6) -0.0534(6) 0.6666(2) 0.039(2) 1.000 . Uani d ? C13 0.6060(6) -0.0690(6) 0.7036(2) 0.037(2) 1.000 . Uani d ? C14 0.6045(7) 0.0056(7) 0.7489(2) 0.036(2) 1.000 . Uani d ? C15 0.5077(7) 0.1026(7) 0.7550(3) 0.039(2) 1.000 . Uani d ? C16 0.4141(6) 0.1191(7) 0.7170(2) 0.039(2) 1.000 . Uani d ? C17 0.6992(8) 0.0531(7) 0.8314(3) 0.057(2) 1.000 . Uani d ? C21 0.2347(5) -0.0981(5) 0.5987(2) 0.033(2) 1.000 . Uani d ? C22 0.3245(7) -0.1664(6) 0.5664(2) 0.043(2) 1.000 . Uani d ? C23 0.2874(6) -0.2823(6) 0.5432(3) 0.042(2) 1.000 . Uani d ? C24 0.1611(7) -0.3331(6) 0.5513(2) 0.037(2) 1.000 . Uani d ? C25 0.0708(7) -0.2676(7) 0.5819(3) 0.046(2) 1.000 . Uani d ? C26 0.1082(6) -0.1488(6) 0.6062(3) 0.043(2) 1.000 . Uani d ? C27 0.0128(8) -0.5107(7) 0.5372(3) 0.052(2) 1.000 . Uani d ? C31 0.1399(5) 0.1281(7) 0.6590(2) 0.034(2) 1.000 . Uani d ? C32 0.0923(7) 0.0694(7) 0.7050(3) 0.053(2) 1.000 . Uani d ? C33 -0.0199(7) 0.1154(9) 0.7287(3) 0.056(2) 1.000 . Uani d ? C34 -0.0869(6) 0.2239(7) 0.7081(2) 0.038(2) 1.000 . Uani d ? C35 -0.0389(7) 0.2825(6) 0.6627(3) 0.047(2) 1.000 . Uani d ? C36 0.0744(6) 0.2334(6) 0.6392(3) 0.043(2) 1.000 . Uani d ? C37 -0.2844(7) 0.3490(8) 0.7071(3) 0.059(2) 1.000 . Uani d ? H1 0.4636 0.2740 0.6123 0.076 1.000 . Uiso c ? H2 0.4936 0.4308 0.5467 0.076 1.000 . Uiso c ? H3 0.2275 0.2426 0.4562 0.076 1.000 . Uiso c ? H4 0.1966 0.0871 0.5211 0.076 1.000 . Uiso c ? H5 0.2095 0.4894 0.4336 0.076 1.000 . Uiso c ? H6 0.3230 0.5409 0.3985 0.076 1.000 . Uiso c ? H7 0.2888 0.3916 0.3992 0.076 1.000 . Uiso c ? H8 0.5114 -0.1073 0.6361 0.076 1.000 . Uiso c ? H9 0.6749 -0.1324 0.6985 0.076 1.000 . Uiso c ? H10 0.5077 0.1575 0.7850 0.076 1.000 . Uiso c ? H11 0.3485 0.1845 0.7213 0.076 1.000 . Uiso c ? H12 0.7002 -0.0066 0.8604 0.076 1.000 . Uiso c ? H13 0.7766 0.1055 0.8323 0.076 1.000 . Uiso c ? H14 0.6234 0.1061 0.8329 0.076 1.000 . Uiso c ? H15 0.4113 -0.1316 0.5608 0.076 1.000 . Uiso c ? H16 0.3473 -0.3278 0.5214 0.076 1.000 . Uiso c ? H17 -0.0153 -0.3019 0.5871 0.076 1.000 . Uiso c ? H18 0.0475 -0.1030 0.6275 0.076 1.000 . Uiso c ? H19 -0.0017 -0.5144 0.5737 0.076 1.000 . Uiso c ? H20 -0.0564 -0.4584 0.5218 0.076 1.000 . Uiso c ? H21 0.0107 -0.5960 0.5228 0.076 1.000 . Uiso c ? H22 0.1380 -0.0035 0.7197 0.076 1.000 . Uiso c ? H23 -0.0524 0.0736 0.7591 0.076 1.000 . Uiso c ? H24 -0.0830 0.3564 0.6483 0.076 1.000 . Uiso c ? H25 0.1054 0.2736 0.6079 0.076 1.000 . Uiso c ? H26 -0.3342 0.3981 0.7313 0.076 1.000 . Uiso c ? H27 -0.2360 0.4069 0.6851 0.076 1.000 . Uiso c ? H28 -0.3427 0.2972 0.6861 0.076 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I 0.0530(3) 0.0548(3) 0.0751(3) -0.0049(2) 0.0136(3) -0.0068(3) P 0.0295(9) 0.0280(8) 0.0379(7) 0.0017(6) 0.0000(7) 0.0001(6) O1 0.060(3) 0.045(3) 0.055(3) -0.002(2) 0.007(2) 0.016(2) O2 0.047(3) 0.047(3) 0.051(2) 0.004(2) -0.017(2) -0.000(2) O3 0.057(4) 0.041(3) 0.079(3) -0.014(2) 0.011(3) -0.023(3) O4 0.043(3) 0.059(3) 0.055(3) 0.016(2) 0.012(2) 0.004(2) C1 0.032(3) 0.026(3) 0.035(3) 0.005(2) 0.010(3) -0.003(2) C2 0.033(4) 0.036(4) 0.045(3) -0.005(3) -0.009(3) -0.003(3) C3 0.045(4) 0.026(3) 0.051(3) -0.008(3) 0.006(3) 0.003(3) C4 0.035(4) 0.027(4) 0.039(3) 0.002(2) 0.007(2) 0.001(3) C5 0.038(4) 0.036(4) 0.037(3) 0.002(3) -0.001(3) 0.006(3) C6 0.050(4) 0.026(4) 0.039(3) -0.005(2) 0.007(3) -0.007(3) C7 0.064(5) 0.059(5) 0.053(4) 0.015(4) 0.008(4) 0.019(3) C11 0.034(4) 0.031(4) 0.038(3) 0.006(3) -0.007(3) 0.005(3) C12 0.044(4) 0.035(4) 0.037(3) -0.000(3) 0.006(3) -0.007(3) C13 0.036(4) 0.035(4) 0.040(3) 0.007(3) 0.001(3) -0.006(3) C14 0.032(4) 0.035(4) 0.040(3) -0.012(3) -0.002(3) 0.008(3) C15 0.040(4) 0.030(5) 0.048(4) -0.001(3) -0.011(3) -0.012(3) C16 0.043(4) 0.028(4) 0.046(3) 0.005(3) 0.002(3) -0.007(3) C17 0.053(5) 0.068(5) 0.049(3) -0.006(4) -0.011(4) -0.007(3) C21 0.035(3) 0.031(4) 0.033(3) -0.002(2) -0.004(3) -0.004(3) C22 0.042(4) 0.045(4) 0.040(3) -0.005(3) 0.003(3) -0.004(3) C23 0.043(4) 0.037(4) 0.046(3) -0.001(3) 0.009(3) -0.013(3) C24 0.042(4) 0.030(4) 0.039(3) 0.002(3) 0.000(3) -0.002(3) C25 0.039(4) 0.037(4) 0.061(4) -0.002(3) -0.003(3) -0.001(3) C26 0.036(3) 0.039(4) 0.055(3) 0.001(3) -0.005(3) -0.007(4) C27 0.059(5) 0.038(4) 0.059(4) -0.010(3) -0.008(4) -0.004(3) C31 0.026(3) 0.037(4) 0.038(3) 0.003(3) -0.001(2) -0.001(3) C32 0.042(4) 0.060(5) 0.056(4) 0.020(3) 0.007(3) 0.013(3) C33 0.050(5) 0.068(5) 0.051(4) 0.012(4) 0.013(3) 0.009(4) C34 0.037(4) 0.046(4) 0.032(3) 0.000(3) 0.000(3) -0.003(3) C35 0.051(4) 0.030(4) 0.061(4) 0.020(3) 0.000(4) 0.010(3) C36 0.046(4) 0.038(4) 0.045(4) 0.008(3) 0.005(3) 0.004(3) C37 0.047(5) 0.059(5) 0.071(4) 0.014(4) 0.009(4) -0.015(4) loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 112 0.000 0.000 'International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2)' H 0 112 0.000 0.000 'International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2)' O 0 16 0.000 0.000 'International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2)' P 0 4 0.000 0.000 'International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2)' I 0 4 0.000 0.000 'International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P C11 112.6(3) . . . ? C1 P C21 107.6(3) . . . ? C1 P C31 107.6(3) . . . ? C11 P C21 111.3(3) . . . ? C11 P C31 108.2(3) . . . ? C21 P C31 109.4(3) . . . ? C4 O1 C7 118.7(5) . . . ? C4 O1 H5 102.7 . . . no C4 O1 H6 146.2 . . . no C4 O1 H7 103.4 . . . no C7 O1 H5 27.4 . . . no C7 O1 H6 27.5 . . . no C7 O1 H7 27.5 . . . no H5 O1 H6 47.0 . . . no H5 O1 H7 47.0 . . . no H6 O1 H7 47.0 . . . no C14 O2 C17 117.6(6) . . . ? C14 O2 H12 132.0 . . . no C14 O2 H13 124.7 . . . no C14 O2 H14 91.0 . . . no C17 O2 H12 27.9 . . . no C17 O2 H13 27.2 . . . no C17 O2 H14 26.9 . . . no H12 O2 H13 46.9 . . . no H12 O2 H14 46.9 . . . no H13 O2 H14 46.9 . . . no C24 O3 C27 117.2(6) . . . ? C24 O3 H19 98.0 . . . no C24 O3 H20 105.0 . . . no C24 O3 H21 143.4 . . . no C27 O3 H19 27.1 . . . no C27 O3 H20 27.8 . . . no C27 O3 H21 26.7 . . . no H19 O3 H20 46.7 . . . no H19 O3 H21 46.6 . . . no H20 O3 H21 46.7 . . . no C34 O4 C37 117.8(5) . . . ? C34 O4 H26 141.3 . . . no C34 O4 H27 94.7 . . . no C34 O4 H28 111.8 . . . no C37 O4 H26 26.8 . . . no C37 O4 H27 27.2 . . . no C37 O4 H28 27.5 . . . no H26 O4 H27 46.6 . . . no H26 O4 H28 46.6 . . . no H27 O4 H28 46.6 . . . no P C1 C2 120.2(5) . . . ? P C1 C6 120.7(5) . . . ? C2 C1 C6 118.8(6) . . . ? C1 C2 C3 118.9(6) . . . ? C1 C2 H1 121.3 . . . no C3 C2 H1 119.7 . . . no C2 C3 C4 120.2(6) . . . ? C2 C3 H2 119.5 . . . no C4 C3 H2 120.4 . . . no O1 C4 C3 115.1(5) . . . ? O1 C4 C5 124.3(6) . . . ? C3 C4 C5 120.6(6) . . . ? C4 C5 C6 119.4(6) . . . ? C4 C5 H3 120.9 . . . no C6 C5 H3 119.7 . . . no C1 C6 C5 122.0(6) . . . ? C1 C6 H4 119.1 . . . no C5 C6 H4 119.0 . . . no O1 C7 H5 109.6 . . . no O1 C7 H6 109.5 . . . no O1 C7 H7 109.4 . . . no H5 C7 H6 109.5 . . . no H5 C7 H7 109.6 . . . no H6 C7 H7 109.3 . . . no P C11 C12 121.4(5) . . . ? P C11 C16 119.8(4) . . . ? C12 C11 C16 118.8(6) . . . ? C11 C12 C13 120.3(6) . . . ? C11 C12 H8 119.8 . . . no C13 C12 H8 119.9 . . . no C12 C13 C14 120.9(6) . . . ? C12 C13 H9 119.9 . . . no C14 C13 H9 119.2 . . . no O2 C14 C13 116.6(6) . . . ? O2 C14 C15 124.3(6) . . . ? C13 C14 C15 119.1(6) . . . ? C14 C15 C16 119.4(7) . . . ? C14 C15 H10 120.2 . . . no C16 C15 H10 120.4 . . . no C11 C16 C15 121.4(6) . . . ? C11 C16 H11 119.3 . . . no C15 C16 H11 119.3 . . . no O2 C17 H12 108.1 . . . no O2 C17 H13 109.4 . . . no O2 C17 H14 109.8 . . . no H12 C17 H13 108.9 . . . no H12 C17 H14 109.7 . . . no H13 C17 H14 110.9 . . . no P C21 C22 120.0(4) . . . ? P C21 C26 120.3(5) . . . ? C22 C21 C26 119.5(6) . . . ? C21 C22 C23 120.0(6) . . . ? C21 C22 H15 119.9 . . . no C23 C22 H15 120.1 . . . no C22 C23 C24 120.2(6) . . . ? C22 C23 H16 120.0 . . . no C24 C23 H16 119.9 . . . no O3 C24 C23 114.9(6) . . . ? O3 C24 C25 123.9(6) . . . ? C23 C24 C25 121.2(6) . . . ? C24 C25 C26 119.1(6) . . . ? C24 C25 H17 121.1 . . . no C26 C25 H17 119.8 . . . no C21 C26 C25 120.0(6) . . . ? C21 C26 H18 119.8 . . . no C25 C26 H18 120.1 . . . no O3 C27 H19 109.9 . . . no O3 C27 H20 108.6 . . . no O3 C27 H21 110.5 . . . no H19 C27 H20 108.3 . . . no H19 C27 H21 110.4 . . . no H20 C27 H21 109.1 . . . no P C31 C32 119.9(5) . . . ? P C31 C36 121.5(5) . . . ? C32 C31 C36 118.6(5) . . . ? C31 C32 C33 120.9(7) . . . ? C31 C32 H22 119.6 . . . no C33 C32 H22 119.5 . . . no C32 C33 C34 120.2(7) . . . ? C32 C33 H23 120.2 . . . no C34 C33 H23 119.6 . . . no O4 C34 C33 116.6(6) . . . ? O4 C34 C35 124.6(6) . . . ? C33 C34 C35 118.8(6) . . . ? C34 C35 C36 119.9(6) . . . ? C34 C35 H24 119.9 . . . no C36 C35 H24 120.2 . . . no C31 C36 C35 121.6(6) . . . ? C31 C36 H25 119.4 . . . no C35 C36 H25 119.0 . . . no O4 C37 H26 110.1 . . . no O4 C37 H27 109.4 . . . no O4 C37 H28 109.1 . . . no H26 C37 H27 110.0 . . . no H26 C37 H28 109.4 . . . no H27 C37 H28 108.8 . . . no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag P C1 1.781(6) . . ? P C11 1.809(6) . . ? P C21 1.794(6) . . ? P C31 1.795(6) . . ? O1 C4 1.362(8) . . ? O1 C7 1.408(9) . . ? O1 H5 1.94 . . no O1 H6 1.94 . . no O1 H7 1.94 . . no O2 C14 1.357(8) . . ? O2 C17 1.421(8) . . ? O2 H12 1.95 . . no O2 H13 1.95 . . no O2 H14 1.95 . . no O3 C24 1.357(7) . . ? O3 C27 1.422(9) . . ? O3 H19 1.96 . . no O3 H20 1.96 . . no O3 H21 1.96 . . no O4 C34 1.339(8) . . ? O4 C37 1.427(10) . . ? O4 H26 1.96 . . no O4 H27 1.96 . . no O4 H28 1.96 . . no C1 C2 1.410(9) . . ? C1 C6 1.376(9) . . ? C2 C3 1.404(10) . . ? C2 H1 0.94 . . no C3 C4 1.388(9) . . ? C3 H2 0.95 . . no C4 C5 1.363(9) . . ? C5 C6 1.383(10) . . ? C5 H3 0.95 . . no C6 H4 0.95 . . no C7 H5 0.95 . . no C7 H6 0.95 . . no C7 H7 0.95 . . no C11 C12 1.388(9) . . ? C11 C16 1.382(9) . . ? C12 C13 1.366(9) . . ? C12 H8 0.95 . . no C13 C14 1.386(9) . . ? C13 H9 0.96 . . no C14 C15 1.397(10) . . ? C15 C16 1.370(9) . . ? C15 H10 0.95 . . no C16 H11 0.95 . . no C17 H12 0.96 . . no C17 H13 0.95 . . no C17 H14 0.94 . . no C21 C22 1.412(9) . . ? C21 C26 1.394(8) . . ? C22 C23 1.369(9) . . ? C22 H15 0.96 . . no C23 C24 1.395(10) . . ? C23 H16 0.95 . . no C24 C25 1.376(10) . . ? C25 C26 1.408(10) . . ? C25 H17 0.95 . . no C26 H18 0.94 . . no C27 H19 0.95 . . no C27 H20 0.96 . . no C27 H21 0.94 . . no C31 C32 1.408(10) . . ? C31 C36 1.355(9) . . ? C32 C33 1.370(10) . . ? C32 H22 0.95 . . no C33 C34 1.395(11) . . ? C33 H23 0.95 . . no C34 C35 1.396(10) . . ? C35 C36 1.389(9) . . ? C35 H24 0.95 . . no C36 H25 0.96 . . no C37 H26 0.94 . . no C37 H27 0.95 . . no C37 H28 0.96 . . no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag I H2 3.1402 . 1_545 no I H27 3.1464 . 1_645 no I H17 3.1470 . 1_655 no I C37 3.871(9) . 1_645 no O1 H16 2.7639 . 1_565 no O1 O3 3.202(7) . 1_565 no O1 H18 3.2022 . 3_556 no O1 H4 3.2198 . 3_556 no O1 C26 3.484(8) . 3_556 no O1 C23 3.579(8) . 1_565 no O1 C36 3.706(9) . 3_556 no O1 C25 3.888(8) . 3_556 no O2 H23 2.7892 . 1_655 no O2 H11 3.0052 . 4_646 no O2 O4 3.362(7) . 1_655 no O2 C33 3.495(10) . 1_655 no O2 C16 3.801(8) . 4_646 no O2 C34 3.858(9) . 1_655 no O2 C36 3.900(9) . 4_646 no O3 H5 2.5802 . 1_545 no O3 C4 3.127(9) . 1_545 no O3 C7 3.284(10) . 1_545 no O3 H15 3.3009 . 3_446 no O3 C5 3.493(9) . 1_545 no O3 C3 3.577(9) . 1_545 no O4 H22 2.7123 . 4_556 no O4 H13 3.0092 . 1_455 no O4 C14 3.329(9) . 1_455 no O4 C17 3.460(9) . 1_455 no O4 C15 3.465(10) . 1_455 no O4 C32 3.632(9) . 4_556 no C1 H21 3.2132 . 3_546 no C1 C27 3.787(9) . 3_546 no C2 H12 2.9678 . 4_656 no C2 C17 3.834(10) . 4_656 no C3 H12 3.1388 . 4_656 no C3 H4 3.1765 . 3_556 no C3 H3 3.1786 . 3_556 no C3 H21 3.2659 . 3_546 no C3 H16 3.3004 . 1_565 no C3 C6 3.736(10) . 3_556 no C3 C5 3.737(9) . 3_556 no C3 C23 3.890(10) . 1_565 no C4 H21 3.0591 . 3_546 no C4 H16 3.3006 . 1_565 no C4 C27 3.895(10) . 3_546 no C5 H21 2.8747 . 3_546 no C5 H21 3.2169 . 1_565 no C5 C27 3.489(10) . 3_546 no C5 C27 3.803(11) . 1_565 no C6 H21 2.9526 . 3_546 no C6 H20 3.0509 . 3_546 no C6 C27 3.428(10) . 3_546 no C7 H18 3.1453 . 3_556 no C7 C26 3.724(11) . 3_556 no C7 C35 3.725(12) . 3_556 no C7 C12 3.726(10) . 3_456 no C7 C36 3.819(11) . 3_556 no C7 C13 3.832(10) . 3_456 no C11 H26 2.9560 . 4_546 no C11 C37 3.862(10) . 4_546 no C12 H10 3.1869 . 4_646 no C12 H26 3.2101 . 4_546 no C13 H10 3.0143 . 4_646 no C13 H11 3.1880 . 4_646 no C13 H26 3.2375 . 4_546 no C13 C15 3.677(10) . 4_646 no C13 C16 3.766(10) . 4_646 no C14 H26 2.9904 . 4_546 no C14 C37 3.783(10) . 4_546 no C14 C37 3.810(11) . 1_655 no C15 H26 2.7397 . 4_546 no C15 H28 3.0521 . 1_655 no C15 C37 3.490(12) . 1_655 no C15 C37 3.559(10) . 4_546 no C16 H26 2.7253 . 4_546 no C16 H28 3.1552 . 1_655 no C16 C37 3.608(10) . 4_546 no C16 C37 3.849(11) . 1_655 no C17 H23 3.1333 . 1_655 no C17 C24 3.524(10) . 4_656 no C17 C23 3.630(10) . 4_656 no C17 C25 3.700(10) . 4_656 no C17 C22 3.876(9) . 4_656 no C22 H20 2.8606 . 3_546 no C22 C27 3.734(10) . 3_546 no C24 H13 3.1185 . 4_646 no C24 H12 3.1949 . 4_646 no C25 H13 2.9836 . 4_646 no C26 H6 3.0910 . 3_456 no C26 H13 3.1715 . 4_646 no C27 H25 2.9912 . 1_545 no C27 H15 3.0768 . 3_446 no C27 H24 3.3014 . 1_545 no C27 C36 3.738(10) . 1_545 no C27 C35 3.880(11) . 1_545 no C32 C37 3.725(10) . 4_546 no C34 H7 3.2493 . 3_456 no C35 H7 2.9486 . 3_456 no C35 H19 3.0990 . 1_565 no C36 H19 3.1548 . 1_565 no C36 H7 3.3088 . 3_456 no C37 H22 2.8237 . 4_556 no H1 H28 2.7377 . 1_655 no H1 H12 2.8620 . 4_656 no H2 H4 2.7006 . 3_556 no H6 H18 2.4521 . 3_556 no H9 H11 2.7810 . 4_646 no H9 H10 2.8513 . 4_646 no H13 H23 2.5766 . 1_655 no H15 H20 2.3310 . 3_546 no H19 H24 2.4627 . 1_545 no H19 H25 2.5611 . 1_545 no H21 H25 2.7265 . 1_545 no H22 H26 2.5551 . 4_546 no H22 H27 2.7909 . 4_546 no 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag P C1 C2 C3 . . . . -171.1(5) no P C1 C6 C5 . . . . 171.8(5) no P C11 C12 C13 . . . . -177.0(5) no P C11 C16 C15 . . . . 175.6(6) no P C21 C22 C23 . . . . -176.5(6) no P C21 C26 C25 . . . . 176.2(5) no P C31 C32 C33 . . . . -175.4(7) no P C31 C36 C35 . . . . 175.9(6) no O1 C4 C3 C2 . . . . 179.8(6) no O1 C4 C5 C6 . . . . -179.2(6) no O2 C14 C13 C12 . . . . 175.7(6) no O2 C14 C15 C16 . . . . -177.0(6) no O3 C24 C23 C22 . . . . -179.4(7) no O3 C24 C25 C26 . . . . 179.1(7) no O4 C34 C33 C32 . . . . -179.7(8) no O4 C34 C35 C36 . . . . -179.7(7) no C1 P C11 C12 . . . . -86.9(6) no C1 P C11 C16 . . . . 95.1(6) no C1 P C21 C22 . . . . 57.0(6) no C1 P C21 C26 . . . . -118.8(6) no C1 P C31 C32 . . . . -174.5(6) no C1 P C31 C36 . . . . 8.6(7) no C1 C2 C3 C4 . . . . -0.7(10) no C1 C6 C5 C4 . . . . -0.8(10) no C2 C1 P C11 . . . . -27.8(7) no C2 C1 P C21 . . . . -150.9(6) no C2 C1 P C31 . . . . 91.3(6) no C2 C1 C6 C5 . . . . -2.0(10) no C2 C3 C4 C5 . . . . -2.1(11) no C3 C2 C1 C6 . . . . 2.7(10) no C3 C4 O1 C7 . . . . -163.7(6) no C3 C4 C5 C6 . . . . 2.9(11) no C5 C4 O1 C7 . . . . 18.3(10) no C6 C1 P C11 . . . . 158.5(5) no C6 C1 P C21 . . . . 35.4(6) no C6 C1 P C31 . . . . -82.4(6) no C11 P C21 C22 . . . . -66.8(6) no C11 P C21 C26 . . . . 117.4(6) no C11 P C31 C32 . . . . -52.5(7) no C11 P C31 C36 . . . . 130.5(6) no C11 C12 C13 C14 . . . . 1.8(11) no C11 C16 C15 C14 . . . . 0.9(11) no C12 C11 P C21 . . . . 34.1(7) no C12 C11 P C31 . . . . 154.4(6) no C12 C11 C16 C15 . . . . -2.5(11) no C12 C13 C14 C15 . . . . -3.4(11) no C13 C12 C11 C16 . . . . 1.1(11) no C13 C14 O2 C17 . . . . 179.4(6) no C13 C14 C15 C16 . . . . 2.0(11) no C15 C14 O2 C17 . . . . -1.4(10) no C16 C11 P C21 . . . . -144.0(5) no C16 C11 P C31 . . . . -23.7(7) no C21 P C31 C32 . . . . 68.9(6) no C21 P C31 C36 . . . . -108.0(6) no C21 C22 C23 C24 . . . . 0.1(10) no C21 C26 C25 C24 . . . . 0.7(11) no C22 C21 P C31 . . . . 173.6(5) no C22 C21 C26 C25 . . . . 0.4(10) no C22 C23 C24 C25 . . . . 1.0(11) no C23 C22 C21 C26 . . . . -0.7(10) no C23 C24 O3 C27 . . . . 174.8(7) no C23 C24 C25 C26 . . . . -1.3(11) no C25 C24 O3 C27 . . . . -5.6(10) no C26 C21 P C31 . . . . -2.2(6) no C31 C32 C33 C34 . . . . -1.7(13) no C31 C36 C35 C34 . . . . 0.6(11) no C32 C31 C36 C35 . . . . -1.1(11) no C32 C33 C34 C35 . . . . 1.1(12) no C33 C32 C31 C36 . . . . 1.6(12) no C33 C34 O4 C37 . . . . -163.8(7) no C33 C34 C35 C36 . . . . -0.6(11) no C35 C34 O4 C37 . . . . 15.4(11) no