Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2001 data_ito004d-283k _database_code_CSD 164081 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Harada, Nobuyuki' 'Ito, Shunji' 'Kabuto, Chizuko' 'Morita, Noboru' 'Watanabe, Masataka' 'Yokoyama, Ryuji' _publ_contact_author_name 'Prof Noboru Morita' _publ_contact_author_address ; Prof Noboru Morita Department of Chemistry Graduate School of Science Tohoku University Sendai 980 8578 JAPAN ; _publ_contact_author_email 'MORITA@FUNORG.CHEM.TOHOKU.AC.JP' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C11 H9 Cl3 O2 ' _chemical_formula_moiety '?' _chemical_formula_weight 279.55 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,-z -x,-y,-z 1/2+x,1/2-y,z _cell_length_a 9.751(1) _cell_length_b 18.486(1) _cell_length_c 14.7287(6) _cell_angle_alpha 90 _cell_angle_beta 115.7591(4) _cell_angle_gamma 90 _cell_volume 2391.1(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 5113 _cell_measurement_theta_min ? _cell_measurement_theta_max 27.5 _cell_measurement_temperature 293.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'plate' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.745 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 1.000 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku/MSC CCD' _diffrn_detector_area_resol_mean 7.31 _diffrn_measurement_method \w _diffrn_reflns_number 20686 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9306 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9306 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 2.9 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 3.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5096 _reflns_number_gt 2442 _reflns_threshold_expression F^2^>3.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.0421 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2442 _refine_ls_number_parameters 289 _refine_ls_goodness_of_fit_ref 0.938 _refine_ls_weighting_scheme unit _refine_ls_shift/su_max 0.0002 _refine_diff_density_max 0.21 _refine_diff_density_min -0.22 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'O' 'O' 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'Cl' 'Cl' 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 Cl(1) Cl 0.3385(2) 0.03754(8) 0.6464(1) 0.0686(4) Uani 1.00 d . . . Cl(2) Cl 0.0340(2) 0.06687(8) 0.4308(1) 0.0718(5) Uani 1.00 d . . . Cl(3) Cl 0.2677(2) 0.04789(8) 0.3622(1) 0.0712(5) Uani 1.00 d . . . Cl(4) Cl 0.0459(2) -0.24270(8) 0.1542(1) 0.0850(6) Uani 1.00 d . . . Cl(5) Cl -0.2417(2) -0.20051(7) -0.0512(1) 0.0763(5) Uani 1.00 d . . . Cl(6) Cl -0.4362(1) -0.10894(8) -0.00285(10) 0.0628(4) Uani 1.00 d . . . O(1) O 0.6418(4) 0.1289(2) 0.6574(3) 0.073(1) Uani 1.00 d . . . O(2) O 0.4408(3) 0.1631(2) 0.5112(2) 0.0422(8) Uani 1.00 d . . . O(3) O -0.0811(4) -0.2020(2) 0.3276(3) 0.082(1) Uani 1.00 d . . . O(4) O -0.1994(3) -0.1214(2) 0.2001(2) 0.0498(9) Uani 1.00 d . . . C(1) C 0.5096(5) 0.1379(2) 0.6076(4) 0.048(1) Uani 1.00 d . . . C(2) C 0.3623(5) 0.1273(2) 0.6165(3) 0.045(1) Uani 1.00 d . . . C(3) C 0.2873(5) 0.1526(2) 0.5066(3) 0.038(1) Uani 1.00 d . . . C(4) C 0.1846(5) 0.2196(2) 0.4631(3) 0.040(1) Uani 1.00 d . . . C(5) C 0.2549(5) 0.2942(3) 0.4728(3) 0.050(1) Uani 1.00 d . . . C(6) C 0.1526(6) 0.3452(3) 0.3936(4) 0.055(2) Uani 1.00 d . . . C(7) C 0.1212(6) 0.3380(3) 0.2975(4) 0.063(2) Uani 1.00 d . . . C(8) C 0.1741(6) 0.2782(3) 0.2565(4) 0.063(2) Uani 1.00 d . . . C(9) C 0.1850(6) 0.2099(3) 0.2856(4) 0.055(2) Uani 1.00 d . . . C(10) C 0.1211(5) 0.1832(3) 0.3566(3) 0.045(1) Uani 1.00 d . . . C(11) C 0.1824(5) 0.1108(3) 0.4115(3) 0.046(1) Uani 1.00 d . . . C(12) C -0.0886(5) -0.1694(3) 0.2575(4) 0.056(2) Uani 1.00 d . . . C(13) C 0.0006(5) -0.1610(3) 0.1952(4) 0.051(1) Uani 1.00 d . . . C(14) C -0.1345(4) -0.1117(2) 0.1277(3) 0.035(1) Uani 1.00 d . . . C(15) C -0.1027(5) -0.0338(2) 0.1049(3) 0.038(1) Uani 1.00 d . . . C(16) C -0.1818(6) 0.0259(3) 0.1336(4) 0.052(1) Uani 1.00 d . . . C(17) C -0.1567(6) 0.0979(3) 0.0959(5) 0.064(2) Uani 1.00 d . . . C(18) C -0.2009(6) 0.1146(3) 0.0001(5) 0.062(2) Uani 1.00 d . . . C(19) C -0.2818(6) 0.0674(3) -0.0851(4) 0.061(2) Uani 1.00 d . . . C(20) C -0.2767(6) -0.0042(3) -0.0895(3) 0.052(1) Uani 1.00 d . . . C(21) C -0.1750(5) -0.0537(2) -0.0087(3) 0.039(1) Uani 1.00 d . . . C(22) C -0.2449(5) -0.1211(2) 0.0148(3) 0.039(1) Uani 1.00 d . . . H(1) H 0.3354 0.1651 0.6625 0.0848 Uiso 1.00 calc . . . H(2) H 0.0914 0.2201 0.4853 0.0848 Uiso 1.00 calc . . . H(3) H 0.2778 0.3130 0.5367 0.0848 Uiso 1.00 calc . . . H(4) H 0.3640 0.2854 0.4720 0.0848 Uiso 1.00 calc . . . H(5) H 0.1275 0.3929 0.4181 0.0848 Uiso 1.00 calc . . . H(6) H 0.0590 0.3732 0.2459 0.0848 Uiso 1.00 calc . . . H(7) H 0.1691 0.2865 0.1857 0.0848 Uiso 1.00 calc . . . H(8) H 0.2121 0.1618 0.2457 0.0848 Uiso 1.00 calc . . . H(9) H 0.0139 0.1862 0.3280 0.0848 Uiso 1.00 calc . . . H(10) H 0.0935 -0.1212 0.2269 0.0848 Uiso 1.00 calc . . . H(11) H 0.0083 -0.0274 0.1244 0.0848 Uiso 1.00 calc . . . H(12) H -0.2934 0.0157 0.1150 0.0848 Uiso 1.00 calc . . . H(13) H -0.1423 0.0207 0.2101 0.0848 Uiso 1.00 calc . . . H(14) H -0.0922 0.1386 0.1479 0.0848 Uiso 1.00 calc . . . H(15) H -0.1702 0.1693 -0.0180 0.0848 Uiso 1.00 calc . . . H(16) H -0.3571 0.0937 -0.1514 0.0848 Uiso 1.00 calc . . . H(17) H -0.3339 -0.0242 -0.1626 0.0848 Uiso 1.00 calc . . . H(18) H -0.0835 -0.0776 -0.0268 0.0848 Uiso 1.00 calc . . . 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 Cl(1) 0.0813(10) 0.0535(8) 0.0704(9) -0.0015(7) 0.0323(8) 0.0141(7) Cl(2) 0.0553(8) 0.0775(10) 0.0786(9) -0.0274(7) 0.0253(7) -0.0010(8) Cl(3) 0.0838(10) 0.0596(8) 0.0720(9) 0.0002(8) 0.0354(8) -0.0232(7) Cl(4) 0.082(1) 0.0661(10) 0.110(1) 0.0395(8) 0.0454(10) 0.0286(9) Cl(5) 0.112(1) 0.0427(7) 0.0668(9) -0.0016(8) 0.0319(9) -0.0129(7) Cl(6) 0.0296(6) 0.0819(9) 0.0655(8) -0.0021(6) 0.0102(5) 0.0154(7) O(1) 0.039(2) 0.084(3) 0.074(3) 0.004(2) 0.004(2) 0.007(2) O(2) 0.032(2) 0.049(2) 0.044(2) 0.002(1) 0.016(1) 0.001(2) O(3) 0.075(3) 0.106(3) 0.055(2) 0.001(2) 0.018(2) 0.040(2) O(4) 0.045(2) 0.065(2) 0.041(2) 0.004(2) 0.021(1) 0.009(2) C(1) 0.048(3) 0.040(3) 0.049(3) 0.002(2) 0.015(2) -0.005(2) C(2) 0.048(3) 0.039(3) 0.047(3) 0.004(2) 0.020(2) 0.004(2) C(3) 0.031(2) 0.044(2) 0.041(2) 0.000(2) 0.019(2) -0.003(2) C(4) 0.033(2) 0.049(3) 0.040(2) 0.002(2) 0.018(2) -0.002(2) C(5) 0.048(3) 0.047(3) 0.052(3) 0.001(2) 0.019(2) 0.003(2) C(6) 0.049(3) 0.050(3) 0.065(3) 0.007(2) 0.024(3) 0.009(3) C(7) 0.053(3) 0.063(4) 0.070(4) 0.008(3) 0.023(3) 0.022(3) C(8) 0.067(4) 0.075(4) 0.044(3) 0.000(3) 0.023(3) 0.011(3) C(9) 0.057(3) 0.065(3) 0.042(3) 0.000(3) 0.021(2) 0.000(3) C(10) 0.031(2) 0.057(3) 0.043(3) 0.000(2) 0.011(2) -0.002(2) C(11) 0.043(3) 0.047(3) 0.053(3) -0.010(2) 0.024(2) -0.013(2) C(12) 0.043(3) 0.069(4) 0.043(3) -0.005(3) 0.006(2) 0.009(3) C(13) 0.038(3) 0.048(3) 0.060(3) 0.008(2) 0.015(2) 0.016(2) C(14) 0.028(2) 0.041(2) 0.036(2) 0.006(2) 0.013(2) 0.007(2) C(15) 0.032(2) 0.036(2) 0.044(2) 0.003(2) 0.013(2) 0.004(2) C(16) 0.060(3) 0.047(3) 0.047(3) 0.007(2) 0.022(2) -0.004(2) C(17) 0.061(3) 0.042(3) 0.088(4) 0.004(3) 0.031(3) -0.015(3) C(18) 0.068(4) 0.036(3) 0.094(4) 0.007(3) 0.046(3) 0.005(3) C(19) 0.065(3) 0.053(3) 0.067(4) 0.016(3) 0.032(3) 0.025(3) C(20) 0.061(3) 0.056(3) 0.042(3) 0.007(3) 0.026(2) 0.011(2) C(21) 0.041(2) 0.033(2) 0.047(3) 0.004(2) 0.023(2) 0.003(2) C(22) 0.034(2) 0.037(2) 0.040(2) 0.001(2) 0.013(2) -0.002(2) #------------------------------------------------------------------------------ _computing_data_collection '.' _computing_cell_refinement '.' _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 Cl(1) C(2) 1.758(4) . . yes Cl(2) C(11) 1.787(4) . . yes Cl(3) C(11) 1.760(5) . . yes Cl(4) C(13) 1.752(5) . . yes Cl(5) C(22) 1.768(4) . . yes Cl(6) C(22) 1.782(4) . . yes O(1) C(1) 1.186(5) . . yes O(2) C(1) 1.361(5) . . yes O(2) C(3) 1.480(5) . . yes O(3) C(12) 1.170(6) . . yes O(4) C(12) 1.368(6) . . yes O(4) C(14) 1.469(5) . . yes C(1) C(2) 1.511(6) . . yes C(2) C(3) 1.531(6) . . yes C(2) H(1) 1.082 . . no C(3) C(4) 1.547(6) . . yes C(3) C(11) 1.536(6) . . yes C(4) C(5) 1.519(6) . . yes C(4) C(10) 1.566(6) . . yes C(4) H(2) 1.091 . . no C(5) C(6) 1.493(6) . . yes C(5) H(3) 0.935 . . no C(5) H(4) 1.082 . . no C(6) C(7) 1.318(7) . . yes C(6) H(5) 1.022 . . no C(7) C(8) 1.458(8) . . yes C(7) H(6) 0.984 . . no C(8) C(9) 1.323(7) . . yes C(8) H(7) 1.034 . . no C(9) C(10) 1.514(7) . . yes C(9) H(8) 1.159 . . no C(10) C(11) 1.542(6) . . yes C(10) H(9) 0.944 . . no C(12) C(13) 1.523(7) . . yes C(13) C(14) 1.555(6) . . yes C(13) H(10) 1.101 . . no C(14) C(15) 1.541(6) . . yes C(14) C(22) 1.549(5) . . yes C(15) C(16) 1.508(6) . . yes C(15) C(21) 1.552(6) . . yes C(15) H(11) 0.999 . . no C(16) C(17) 1.503(7) . . yes C(16) H(12) 1.018 . . no C(16) H(13) 1.025 . . no C(17) C(18) 1.320(8) . . yes C(17) H(14) 1.062 . . no C(18) C(19) 1.448(8) . . yes C(18) H(15) 1.121 . . no C(19) C(20) 1.327(7) . . yes C(19) H(16) 1.053 . . no C(20) C(21) 1.487(6) . . yes C(20) H(17) 1.042 . . no C(21) C(22) 1.531(6) . . yes C(21) H(18) 1.126 . . no #------------------------------------------------------------------------------ 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 C(1) O(2) C(3) 91.9(3) . 1_555 1_555 yes C(12) O(4) C(14) 93.2(3) . 1_555 1_555 yes O(1) C(1) O(2) 127.1(5) . 1_555 1_555 yes O(1) C(1) C(2) 138.3(5) . 1_555 1_555 yes O(2) C(1) C(2) 94.5(3) . 1_555 1_555 yes Cl(1) C(2) C(1) 112.2(3) . 1_555 1_555 yes Cl(1) C(2) C(3) 119.9(3) . 1_555 1_555 yes Cl(1) C(2) H(1) 111.0 . 1_555 1_555 no C(1) C(2) C(3) 84.5(3) . 1_555 1_555 yes C(1) C(2) H(1) 117.9 . 1_555 1_555 no C(3) C(2) H(1) 109.3 . 1_555 1_555 no O(2) C(3) C(2) 89.0(3) . 1_555 1_555 yes O(2) C(3) C(4) 111.9(3) . 1_555 1_555 yes O(2) C(3) C(11) 111.6(3) . 1_555 1_555 yes C(2) C(3) C(4) 127.4(4) . 1_555 1_555 yes C(2) C(3) C(11) 129.3(4) . 1_555 1_555 yes C(4) C(3) C(11) 88.3(3) . 1_555 1_555 yes C(3) C(4) C(5) 120.3(3) . 1_555 1_555 yes C(3) C(4) C(10) 88.5(3) . 1_555 1_555 yes C(3) C(4) H(2) 110.9 . 1_555 1_555 no C(5) C(4) C(10) 116.8(4) . 1_555 1_555 yes C(5) C(4) H(2) 111.4 . 1_555 1_555 no C(10) C(4) H(2) 106.6 . 1_555 1_555 no C(4) C(5) C(6) 112.2(4) . 1_555 1_555 yes C(4) C(5) H(3) 109.4 . 1_555 1_555 no C(4) C(5) H(4) 105.5 . 1_555 1_555 no C(6) C(5) H(3) 109.7 . 1_555 1_555 no C(6) C(5) H(4) 114.4 . 1_555 1_555 no H(3) C(5) H(4) 105.2 . 1_555 1_555 no C(5) C(6) C(7) 122.7(5) . 1_555 1_555 yes C(5) C(6) H(5) 116.7 . 1_555 1_555 no C(7) C(6) H(5) 119.0 . 1_555 1_555 no C(6) C(7) C(8) 124.2(5) . 1_555 1_555 yes C(6) C(7) H(6) 122.7 . 1_555 1_555 no C(8) C(7) H(6) 113.0 . 1_555 1_555 no C(7) C(8) C(9) 125.6(5) . 1_555 1_555 yes C(7) C(8) H(7) 115.9 . 1_555 1_555 no C(9) C(8) H(7) 115.5 . 1_555 1_555 no C(8) C(9) C(10) 122.5(5) . 1_555 1_555 yes C(8) C(9) H(8) 124.9 . 1_555 1_555 no C(10) C(9) H(8) 110.6 . 1_555 1_555 no C(4) C(10) C(9) 116.7(4) . 1_555 1_555 yes C(4) C(10) C(11) 87.4(3) . 1_555 1_555 yes C(4) C(10) H(9) 107.5 . 1_555 1_555 no C(9) C(10) C(11) 117.6(4) . 1_555 1_555 yes C(9) C(10) H(9) 112.3 . 1_555 1_555 no C(11) C(10) H(9) 112.8 . 1_555 1_555 no Cl(2) C(11) Cl(3) 109.0(2) . 1_555 1_555 yes Cl(2) C(11) C(3) 110.4(3) . 1_555 1_555 yes Cl(2) C(11) C(10) 108.8(3) . 1_555 1_555 yes Cl(3) C(11) C(3) 117.4(3) . 1_555 1_555 yes Cl(3) C(11) C(10) 120.1(3) . 1_555 1_555 yes C(3) C(11) C(10) 89.7(3) . 1_555 1_555 yes O(3) C(12) O(4) 127.5(5) . 1_555 1_555 yes O(3) C(12) C(13) 138.7(5) . 1_555 1_555 yes O(4) C(12) C(13) 93.8(4) . 1_555 1_555 yes Cl(4) C(13) C(12) 114.6(3) . 1_555 1_555 yes Cl(4) C(13) C(14) 123.8(3) . 1_555 1_555 yes Cl(4) C(13) H(10) 116.0 . 1_555 1_555 no C(12) C(13) C(14) 84.1(3) . 1_555 1_555 yes C(12) C(13) H(10) 113.0 . 1_555 1_555 no C(14) C(13) H(10) 101.0 . 1_555 1_555 no O(4) C(14) C(13) 88.6(3) . 1_555 1_555 yes O(4) C(14) C(15) 117.7(3) . 1_555 1_555 yes O(4) C(14) C(22) 116.6(3) . 1_555 1_555 yes C(13) C(14) C(15) 119.5(3) . 1_555 1_555 yes C(13) C(14) C(22) 128.4(4) . 1_555 1_555 yes C(15) C(14) C(22) 89.1(3) . 1_555 1_555 yes C(14) C(15) C(16) 116.5(4) . 1_555 1_555 yes C(14) C(15) C(21) 88.4(3) . 1_555 1_555 yes C(14) C(15) H(11) 110.1 . 1_555 1_555 no C(16) C(15) C(21) 115.4(3) . 1_555 1_555 yes C(16) C(15) H(11) 117.1 . 1_555 1_555 no C(21) C(15) H(11) 105.4 . 1_555 1_555 no C(15) C(16) C(17) 111.0(4) . 1_555 1_555 yes C(15) C(16) H(12) 114.0 . 1_555 1_555 no C(15) C(16) H(13) 104.3 . 1_555 1_555 no C(17) C(16) H(12) 113.0 . 1_555 1_555 no C(17) C(16) H(13) 116.4 . 1_555 1_555 no H(12) C(16) H(13) 97.3 . 1_555 1_555 no C(16) C(17) C(18) 124.8(5) . 1_555 1_555 yes C(16) C(17) H(14) 120.1 . 1_555 1_555 no C(18) C(17) H(14) 114.9 . 1_555 1_555 no C(17) C(18) C(19) 126.0(5) . 1_555 1_555 yes C(17) C(18) H(15) 118.0 . 1_555 1_555 no C(19) C(18) H(15) 116.0 . 1_555 1_555 no C(18) C(19) C(20) 128.7(5) . 1_555 1_555 yes C(18) C(19) H(16) 115.0 . 1_555 1_555 no C(20) C(19) H(16) 116.3 . 1_555 1_555 no C(19) C(20) C(21) 127.0(5) . 1_555 1_555 yes C(19) C(20) H(17) 112.9 . 1_555 1_555 no C(21) C(20) H(17) 118.7 . 1_555 1_555 no C(15) C(21) C(20) 123.3(4) . 1_555 1_555 yes C(15) C(21) C(22) 89.3(3) . 1_555 1_555 yes C(15) C(21) H(18) 108.2 . 1_555 1_555 no C(20) C(21) C(22) 118.3(4) . 1_555 1_555 yes C(20) C(21) H(18) 112.0 . 1_555 1_555 no C(22) C(21) H(18) 102.2 . 1_555 1_555 no Cl(5) C(22) Cl(6) 107.0(2) . 1_555 1_555 yes Cl(5) C(22) C(14) 120.9(3) . 1_555 1_555 yes Cl(5) C(22) C(21) 115.8(3) . 1_555 1_555 yes Cl(6) C(22) C(14) 109.8(3) . 1_555 1_555 yes Cl(6) C(22) C(21) 113.9(3) . 1_555 1_555 yes C(14) C(22) C(21) 88.9(3) . 1_555 1_555 yes 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