#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/49/2004946.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2004946 loop_ _publ_author_name 'Protasiewicz, J. D.' _publ_contact_author ; John D. Protasiewicz Department of Chemistry Case Western Reserve University 10900 Euclid Ave Cleveland, OH 44106-7078 ; _publ_section_title ; (Tosyliminoiodo)benzene at 298K ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1570 _journal_page_last 1572 _journal_volume 52 _journal_year 1996 _chemical_formula_sum 'C13 H12 I N O2 S' _chemical_formula_weight 373.20 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 104.520(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.6086(15) _cell_length_b 7.7966(9) _cell_length_c 15.2545(14) _cell_measurement_reflns_used 40 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.2 _cell_measurement_theta_min 9.0 _cell_volume 1336.6(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL-Plus (heldrick, 1994)' _computing_publication_material SHELXTL-Plus _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \q-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3155 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.81 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 2.545 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_type '\y scan (North, Phillips & Matthews, 1968)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.855 _exptl_crystal_density_meas 1.85 _exptl_crystal_density_method floatation _exptl_crystal_description needle _exptl_crystal_F_000 728 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.60 _refine_diff_density_min -0.37 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.11 _refine_ls_goodness_of_fit_obs 1.147 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 2351 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.877 _refine_ls_restrained_S_obs 1.147 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_obs 0.028 _refine_ls_shift/esd_max 0.055 _refine_ls_shift/esd_mean 0.003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0215P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.106 _refine_ls_wR_factor_obs 0.0598 _reflns_number_observed 2043 _reflns_number_total 2352 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file bk1198.cif _[local]_cod_data_source_block phinr2 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2004946 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_type_symbol I 1 .98578(2) .02332(3) .74795(2) .02925(10) Uani d I N 1 .8965(3) -0.1998(4) .7489(2) .0283(7) Uani d N S 1 .75881(9) -0.20367(13) .69143(7) .0299(2) Uani d S O1 1 .7259(3) -.0545(4) .6342(2) .0407(7) Uani d O O2 1 .7390(3) -0.3691(4) .6484(2) .0446(8) Uani d O C1 1 .9262(4) .1480(5) .8514(3) .0326(9) Uani d C C2 1 .8079(4) .1901(6) .8341(3) .0418(11) Uani d C C3 1 .7673(5) .2643(7) .9036(4) .0588(15) Uani d C C4 1 .8438(5) .2962(7) .9863(4) .0557(14) Uani d C C5 1 .9616(6) .2550(7) 1.0007(3) .0554(14) Uani d C C6 1 1.0054(4) .1765(6) .9340(3) .0418(11) Uani d C C7 1 .6725(3) -0.1990(5) .7723(3) .0299(9) Uani d C C8 1 .5673(4) -0.1083(6) .7552(3) .0424(11) Uani d C C9 1 .4979(4) -0.1138(7) .8167(4) .0478(12) Uani d C C10 1 .5317(4) -0.2078(6) .8957(3) .0402(11) Uani d C C11 1 .6377(4) -0.2962(7) .9119(3) .0445(12) Uani d C C12 1 .7081(4) -0.2936(7) .8508(3) .0426(11) Uani d C C13 1 .4556(6) -0.2165(8) .9627(4) .0561(15) Uani d C H2 1 .758(5) .163(7) .774(4) .067 Uiso d H H3 1 .687(5) .288(7) .889(4) .067 Uiso d H H4 1 .816(5) .337(7) 1.028(4) .067 Uiso d H H5 1 1.009(5) .269(7) 1.050(4) .067 Uiso d H H6 1 1.084(5) .154(7) .944(3) .067 Uiso d H H8 1 .551(5) -.051(7) .697(4) .067 Uiso d H H9 1 .425(5) -.066(7) .804(4) .067 Uiso d H H11 1 .665(5) -0.356(7) .966(4) .067 Uiso d H H12 1 .780(5) -0.362(7) .864(3) .067 Uiso d H H13A 1 .494(5) -0.205(7) 1.026(4) .067 Uiso d H H13B 1 .399(5) -0.159(8) .945(4) .067 Uiso d H H13C 1 .426(5) -0.322(7) .957(4) .067 Uiso d H 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 0.03273(15) 0.02744(14) 0.03088(14) -0.00046(11) 0.01412(10) -0.00320(10) N 0.027(2) 0.021(2) 0.038(2) -0.0009(13) 0.0114(15) -0.0003(14) S 0.0291(5) 0.0328(5) 0.0293(5) -0.0014(4) 0.0103(4) -0.0013(4) O1 0.044(2) 0.046(2) 0.0328(15) 0.0034(15) 0.0101(13) 0.0099(14) O2 0.042(2) 0.043(2) 0.051(2) -0.0101(15) 0.0174(15) -0.018(2) C1 0.045(2) 0.028(2) 0.033(2) 0.000(2) 0.024(2) -0.002(2) C2 0.038(3) 0.044(3) 0.046(3) 0.003(2) 0.015(2) -0.011(2) C3 0.045(3) 0.061(4) 0.078(4) 0.002(3) 0.029(3) -0.019(3) C4 0.064(4) 0.062(3) 0.052(3) -0.002(3) 0.037(3) -0.019(3) C5 0.068(4) 0.064(4) 0.037(3) -0.006(3) 0.020(3) -0.012(2) C6 0.048(3) 0.043(3) 0.036(2) -0.002(2) 0.013(2) -0.006(2) C7 0.027(2) 0.035(2) 0.029(2) 0.000(2) 0.009(2) -0.003(2) C8 0.039(3) 0.045(3) 0.045(3) 0.011(2) 0.014(2) 0.012(2) C9 0.039(3) 0.047(3) 0.063(3) 0.010(2) 0.023(2) 0.005(2) C10 0.040(3) 0.042(3) 0.044(3) -0.011(2) 0.022(2) -0.008(2) C11 0.044(3) 0.058(3) 0.033(2) 0.001(2) 0.013(2) 0.009(2) C12 0.032(2) 0.053(3) 0.044(3) 0.005(2) 0.011(2) 0.011(2) C13 0.059(4) 0.063(4) 0.059(3) -0.011(3) 0.038(3) -0.012(3) 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' N N 0.0061 0.0033 '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' S S 0.1246 0.1234 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N I C1 . . 97.22(14) yes N I N . 2_756 178.09(6) yes C1 I N . 2_756 82.57(13) ? N I C2 . . 87.69(13) ? C1 I C2 . . 23.79(15) ? N I C2 2_756 . 92.82(12) ? N I C6 . . 104.45(13) ? C1 I C6 . . 23.35(15) ? N I C6 2_756 . 74.63(12) ? C2 I C6 . . 47.13(14) ? N I S . . 27.72(9) ? C1 I S . . 93.18(12) ? N I S 2_756 . 154.13(7) ? C2 I S . . 74.96(9) ? C6 I S . . 110.04(10) ? S N I . . 116.7(2) yes S N I . 2_746 116.5(2) ? I N I . 2_746 117.03(13) yes O2 S O1 . . 117.2(2) yes O2 S N . . 106.7(2) yes O1 S N . . 112.8(2) yes O2 S C7 . . 106.4(2) yes O1 S C7 . . 107.1(2) yes N S C7 . . 106.0(2) ? O2 S I . . 131.58(13) ? O1 S I . . 77.71(13) ? N S I . . 35.61(11) ? C7 S I . . 112.48(14) ? O2 S I . 2_746 67.20(13) ? O1 S I . 2_746 135.25(13) ? N S I . 2_746 39.60(11) ? C7 S I . 2_746 114.11(14) ? I S I . 2_746 71.18(2) ? S O1 I . . 75.52(12) ? S O1 I . 2_746 32.28(10) ? I O1 I . 2_746 55.43(4) ? S O2 I . 2_746 89.08(13) ? S O2 I . . 33.59(10) ? I O2 I 2_746 . 61.42(5) ? C2 C1 C6 . . 122.9(4) ? C2 C1 I . . 117.8(3) ? C6 C1 I . . 119.2(3) ? C2 C1 I . 2_756 95.8(3) ? C6 C1 I . 2_756 93.4(3) ? I C1 I . 2_756 82.96(11) ? C1 C2 C3 . . 117.9(5) ? C1 C2 I . . 38.4(2) ? C3 C2 I . . 156.2(4) ? C1 C2 I . 2_756 63.9(3) ? C3 C2 I . 2_756 108.5(3) ? I C2 I . 2_756 66.92(9) ? C1 C2 H2 . . 118.(3) ? C3 C2 H2 . . 125.(3) ? I C2 H2 . . 79.(3) ? I C2 H2 2_756 . 97.(3) ? C4 C3 C2 . . 120.8(5) ? C4 C3 I . . 104.5(3) ? C2 C3 I . . 16.3(3) ? C4 C3 I . 2_756 92.4(3) ? C2 C3 I . 2_756 54.8(3) ? I C3 I . 2_756 52.08(6) ? C4 C3 H3 . . 125.(4) ? C2 C3 H3 . . 115.(4) ? I C3 H3 . . 131.(3) ? I C3 H3 2_756 . 121.(4) ? C5 C4 C3 . . 119.7(5) ? C5 C4 I . 4_566 77.6(3) ? C3 C4 I . 4_566 162.3(4) ? C5 C4 I . 3_757 63.5(3) ? C3 C4 I . 3_757 136.5(4) ? I C4 I 4_566 3_757 51.57(7) ? C5 C4 I . 2_756 68.1(3) ? C3 C4 I . 2_756 71.2(3) ? I C4 I 4_566 2_756 116.60(12) ? I C4 I 3_757 2_756 131.55(12) ? C5 C4 I . . 60.2(3) ? C3 C4 I . . 59.6(3) ? I C4 I 4_566 . 137.78(14) ? I C4 I 3_757 . 105.25(11) ? I C4 I 2_756 . 47.68(5) ? C5 C4 H4 . . 122.(4) ? C3 C4 H4 . . 119.(4) ? I C4 H4 4_566 . 44.(4) ? I C4 H4 3_757 . 73.(4) ? I C4 H4 2_756 . 136.(4) ? I C4 H4 . . 176.(4) ? C4 C5 C6 . . 121.4(5) ? C4 C5 I . 4_566 83.3(3) ? C6 C5 I . 4_566 155.2(4) ? C4 C5 I . 3_757 100.0(3) ? C6 C5 I . 3_757 115.7(4) ? I C5 I 4_566 3_757 55.37(6) ? C4 C5 I . . 103.9(3) ? C6 C5 I . . 17.5(3) ? I C5 I 4_566 . 172.6(2) ? I C5 I 3_757 . 123.73(14) ? C4 C5 I . 2_756 95.6(3) ? C6 C5 I . 2_756 55.6(3) ? I C5 I 4_566 2_756 125.95(13) ? I C5 I 3_757 2_756 164.4(2) ? I C5 I . 2_756 52.51(6) ? C4 C5 H5 . . 122.(4) ? C6 C5 H5 . . 117.(4) ? I C5 H5 4_566 . 39.(4) ? I C5 H5 3_757 . 49.(4) ? I C5 H5 . . 134.(4) ? I C5 H5 2_756 . 121.(4) ? C1 C6 C5 . . 117.3(5) ? C1 C6 I . . 37.4(2) ? C5 C6 I . . 154.6(4) ? C1 C6 I . 2_756 65.9(2) ? C5 C6 I . 2_756 107.2(3) ? I C6 I . 2_756 67.42(9) ? C1 C6 I . 3_757 132.3(3) ? C5 C6 I . 3_757 50.0(3) ? I C6 I . 3_757 138.80(14) ? I C6 I 2_756 3_757 153.78(12) ? C1 C6 H6 . . 123.(3) ? C5 C6 H6 . . 120.(3) ? I C6 H6 . . 85.(3) ? I C6 H6 2_756 . 93.(3) ? I C6 H6 3_757 . 90.(3) ? C12 C7 C8 . . 119.9(4) ? C12 C7 S . . 119.6(3) ? C8 C7 S . . 120.4(3) ? C12 C7 I . . 102.9(3) ? C8 C7 I . . 121.7(3) ? S C7 I . . 44.12(10) ? C12 C7 I . 2_746 74.4(3) ? C8 C7 I . 2_746 165.3(3) ? S C7 I . 2_746 45.26(10) ? I C7 I . 2_746 52.93(5) ? C7 C8 C9 . . 119.6(4) ? C7 C8 I . . 44.7(2) ? C9 C8 I . . 139.2(3) ? C7 C8 H8 . . 112.(3) ? C9 C8 H8 . . 128.(3) ? I C8 H8 . . 82.(3) ? C10 C9 C8 . . 121.5(4) ? C10 C9 H9 . . 118.(4) ? C8 C9 H9 . . 121.(4) ? C11 C10 C9 . . 117.9(4) ? C11 C10 C13 . . 120.3(5) ? C9 C10 C13 . . 121.8(5) ? C10 C11 C12 . . 121.6(4) ? C10 C11 H11 . . 119.(3) ? C12 C11 H11 . . 119.(3) ? C7 C12 C11 . . 119.5(4) ? C7 C12 I . 2_746 88.2(3) ? C11 C12 I . 2_746 152.0(3) ? C7 C12 I . . 60.2(2) ? C11 C12 I . . 144.4(4) ? I C12 I 2_746 . 51.06(5) ? C7 C12 H12 . . 122.(3) ? C11 C12 H12 . . 119.(3) ? I C12 H12 2_746 . 34.(3) ? I C12 H12 . . 74.(3) ? C10 C13 H13A . . 118.(4) ? C10 C13 H13B . . 108.(5) ? H13A C13 H13B . . 116.(6) ? C10 C13 H13C . . 104.(4) ? H13A C13 H13C . . 105.(5) ? H13B C13 H13C . . 103.(6) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag I N . 2.027(3) yes I C1 . 2.113(4) yes I N 2_756 2.549(3) yes I I 2_746 3.9114(4) yes I C2 . 3.007(4) ? I C6 . 3.034(4) ? I S . 3.1110(11) ? N S . 1.619(3) yes N I 2_746 2.549(3) ? S O2 . 1.439(3) yes S O1 . 1.447(3) yes S C7 . 1.775(4) yes S I 2_746 3.5780(11) ? O1 I 2_746 4.717(3) ? O2 I 2_746 3.299(3) ? C1 C2 . 1.371(6) ? C1 C6 . 1.378(6) ? C1 I 2_756 3.561(4) ? C2 C3 . 1.390(7) ? C2 I 2_756 3.944(5) ? C2 H2 . 0.98(5) ? C3 C4 . 1.371(8) ? C3 I 2_756 4.578(6) ? C3 H3 . 0.92(6) ? C4 C5 . 1.368(8) ? C4 I 4_566 4.163(5) ? C4 I 3_757 4.747(6) ? C4 I 2_756 4.833(5) ? C4 H4 . 0.84(5) ? C5 C6 . 1.389(6) ? C5 I 4_566 4.094(5) ? C5 I 3_757 4.314(5) ? C5 I 2_756 4.505(5) ? C5 H5 . 0.82(6) ? C6 I 2_756 3.894(5) ? C6 I 3_757 5.073(4) ? C6 H6 . 0.91(5) ? C7 C12 . 1.378(6) ? C7 C8 . 1.377(6) ? C7 I 2_746 4.598(4) ? C8 C9 . 1.383(6) ? C8 H8 . 0.97(6) ? C9 C10 . 1.381(7) ? C9 H9 . 0.90(6) ? C10 C11 . 1.377(7) ? C10 C13 . 1.511(6) yes C11 C12 . 1.385(6) ? C11 H11 . 0.93(5) ? C12 I 2_746 4.430(5) ? C12 H12 . 0.97(5) ? C13 H13A . 0.96(6) ? C13 H13B . 0.79(6) ? C13 H13C . 0.88(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 C1 I N S 83.1(2) C6 I N S 105.7(2) S I N S 0.0 I N S O2 140.5(2) I N S O1 10.5(2) I N S C7 -106.4(2) I N S I 0.0 N I S O2 -54.6(3) C1 I S O2 -154.1(2) C2 I S O2 -169.5(2) C6 I S O2 -137.5(2) N I S O1 -170.1(2) C1 I S O1 90.4(2) C2 I S O1 75.0(2) C6 I S O1 107.0(2) N I S N 0.0 C1 I S N -99.5(2) C2 I S N -114.9(2) C6 I S N -82.9(2) N I S C7 86.3(2) C1 I S C7 -13.2(2) C2 I S C7 -28.7(2) C6 I S C7 3.4(2) O2 S O1 I -130.7(2) N S O1 I -6.23(15) C7 S O1 I 110.02(15) I S O1 I 0.0 N I O1 S 5.65(13) C1 I O1 S -91.1(2) C2 I O1 S -96.5(2) C6 I O1 S -84.3(2) S I O1 S 0.0 O1 S O2 I 97.8(2) N S O2 I -29.68(15) C7 S O2 I -142.5(2) I S O2 I 0.0 N I O2 S 95.1(3) C1 I O2 S 27.1(2) C2 I O2 S 10.1(2) C6 I O2 S 47.5(2) S I O2 S 0.0 N I C1 C2 -67.2(4) C2 I C1 C2 0.000(3) C6 I C1 C2 -177.1(6) S I C1 C2 -39.6(3) N I C1 C6 110.0(4) C2 I C1 C6 177.1(6) C6 I C1 C6 0.000(4) S I C1 C6 137.5(3) C6 C1 C2 C3 -0.2(7) I C1 C2 C3 176.8(4) C6 C1 C2 I -177.0(6) I C1 C2 I 0.000(2) N I C2 C1 113.8(4) C1 I C2 C1 0.000(5) C6 I C2 C1 1.6(3) S I C2 C1 138.8(4) N I C2 C3 106.8(9) C1 I C2 C3 -6.9(8) C6 I C2 C3 -5.4(9) S I C2 C3 131.8(10) C1 C2 C3 C4 0.8(8) I C2 C3 C4 5.7(13) C1 C2 C3 I -4.9(6) I C2 C3 I 0.000(4) N I C3 C4 112.1(4) C1 I C3 C4 -4.9(5) C2 I C3 C4 -174.9(12) C6 I C3 C4 -1.1(3) S I C3 C4 138.1(4) N I C3 C2 -73.0(9) C1 I C3 C2 170.0(12) C2 I C3 C2 0.000(13) C6 I C3 C2 173.8(10) S I C3 C2 -47.0(9) C2 C3 C4 C5 0.2(9) I C3 C4 C5 1.8(6) C2 C3 C4 I -1.7(4) I C3 C4 I 0.0000(10) N I C4 C5 113.2(4) C1 I C4 C5 -70.(5) C2 I C4 C5 -176.5(6) C6 I C4 C5 0.1(4) S I C4 C5 140.7(4) N I C4 C3 -68.7(4) C1 I C4 C3 108.(5) C2 I C4 C3 1.7(4) C6 I C4 C3 178.2(6) S I C4 C3 -41.1(4) C3 C4 C5 C6 -1.9(9) I C4 C5 C6 -0.1(4) C3 C4 C5 I -1.8(6) I C4 C5 I 0.0000(10) N I C5 C4 -69.1(4) C1 I C5 C4 5.1(5) C2 I C5 C4 2.2(3) C6 I C5 C4 -179.8(11) S I C5 C4 -40.8(4) N I C5 C6 110.6(9) C1 I C5 C6 -175.1(11) C2 I C5 C6 -178.0(9) C6 I C5 C6 0.000(13) S I C5 C6 139.0(9) C2 C1 C6 C5 -1.5(7) I C1 C6 C5 -178.4(4) C2 C1 C6 I 177.0(6) I C1 C6 I 0.000(2) C4 C5 C6 C1 2.5(8) I C5 C6 C1 2.2(5) C4 C5 C6 I 0.3(12) I C5 C6 I 0.000(3) N I C6 C1 -74.4(4) C1 I C6 C1 0.000(5) C2 I C6 C1 -1.6(3) S I C6 C1 -45.9(4) N I C6 C5 -71.1(9) C1 I C6 C5 3.3(8) C2 I C6 C5 1.7(8) S I C6 C5 -42.6(9) O2 S C7 C12 73.0(4) O1 S C7 C12 -161.0(4) N S C7 C12 -40.3(4) I S C7 C12 -77.5(4) O2 S C7 C8 -103.8(4) O1 S C7 C8 22.2(4) N S C7 C8 142.9(4) I S C7 C8 105.7(4) O2 S C7 I 150.5(2) O1 S C7 I -83.5(2) N S C7 I 37.19(12) I S C7 I 0.0 N I C7 C12 64.3(3) C1 I C7 C12 -74.6(3) C2 I C7 C12 -95.0(3) C6 I C7 C12 -57.4(3) S I C7 C12 119.4(4) N I C7 C8 -157.6(4) C1 I C7 C8 63.5(3) C2 I C7 C8 43.0(3) C6 I C7 C8 80.6(3) S I C7 C8 -102.5(4) N I C7 S -55.1(2) C1 I C7 S 166.0(2) C2 I C7 S 145.5(2) C6 I C7 S -176.8(2) S I C7 S 0.0 C12 C7 C8 C9 -0.3(7) S C7 C8 C9 176.4(4) I C7 C8 C9 -131.6(4) C12 C7 C8 I 131.2(5) S C7 C8 I -52.0(2) I C7 C8 I 0.0 N I C8 C7 17.1(3) C1 I C8 C7 -111.4(4) C2 I C8 C7 -128.7(4) C6 I C8 C7 -98.4(3) S I C8 C7 52.3(3) N I C8 C9 101.6(5) C1 I C8 C9 -26.9(5) C2 I C8 C9 -44.2(5) C6 I C8 C9 -13.8(5) S I C8 C9 136.9(5) C7 C8 C9 C10 0.3(8) I C8 C9 C10 -53.4(7) C8 C9 C10 C11 0.3(7) C8 C9 C10 C13 -179.1(5) C9 C10 C11 C12 -0.8(8) C13 C10 C11 C12 178.6(5) C8 C7 C12 C11 -0.2(7) S C7 C12 C11 -177.0(4) I C7 C12 C11 138.8(4) C8 C7 C12 I -139.0(5) S C7 C12 I 44.2(2) I C7 C12 I 0.0 C10 C11 C12 C7 0.8(8) C10 C11 C12 I 79.9(7) N I C12 C7 -89.5(4) C1 I C12 C7 98.9(3) C2 I C12 C7 73.9(3) C6 I C12 C7 120.6(3) S I C12 C7 -37.4(2) N I C12 C11 170.3(6) C1 I C12 C11 -1.3(5) C2 I C12 C11 -26.3(5) C6 I C12 C11 20.4(5) S I C12 C11 -137.6(6) _journal_paper_doi 10.1107/S0108270195016659