# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Saito, Kazuya' _publ_contact_author_email kazuya@chem.tsukuba.ac.jp _publ_section_title ; Polarization Reversal by Intramolecular Disordering in Organic Ferroelectrics Trichloroacetamide ; loop_ _publ_author_name K.Saito Y.Yamamura N.Kikuchi A.Nakao S.Yasuzuka Yu.Akishige Y.Murakami # Attachment '- HT.CIF' data_HT _database_code_depnum_ccdc_archive 'CCDC 794701' #TrackingRef '- HT.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl3 N O' _chemical_formula_sum 'C2 H2 Cl3 N O' _chemical_formula_weight 162.40 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C 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' _cell_length_a 10.585(11) _cell_length_b 5.881(6) _cell_length_c 10.311(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.90(2) _cell_angle_gamma 90.00 _cell_volume 610.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 370(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.766 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 1.382 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8742 _exptl_absorpt_correction_T_max 0.8742 _exptl_absorpt_process_details 'PROCESS-AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 370(2) _diffrn_radiation_wavelength 0.68890 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator 'Si (111)' _diffrn_measurement_device_type 'IP area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4677 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.68 _diffrn_reflns_theta_max 30.43 _reflns_number_total 1336 _reflns_number_gt 1000 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0898P)^2^+0.0433P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 1.98(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1336 _refine_ls_number_parameters 122 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1575 _refine_ls_wR_factor_gt 0.1475 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.007 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 Cl1 Cl 0.90083(17) 0.2458(3) 0.1640(5) 0.1118(18) Uani 0.518(7) 1 d P . . Cl2 Cl 0.7612(4) -0.1050(6) -0.0119(4) 0.1186(14) Uani 0.518(7) 1 d P . . Cl3 Cl 0.7499(3) -0.0855(5) 0.2567(4) 0.1071(10) Uani 0.518(7) 1 d P . . Cl4 Cl 0.8783(4) 0.1910(15) 0.2782(9) 0.135(4) Uani 0.276(7) 1 d P . . Cl5 Cl 0.8454(9) 0.0449(19) 0.0012(5) 0.158(4) Uani 0.276(7) 1 d P . . Cl6 Cl 0.7134(4) -0.1686(8) 0.1562(12) 0.149(4) Uani 0.276(7) 1 d P . . Cl7 Cl 0.8956(8) 0.210(3) 0.067(2) 0.172(8) Uani 0.206(8) 1 d P . . Cl8 Cl 0.8157(16) 0.032(3) 0.2913(7) 0.157(7) Uani 0.206(8) 1 d P . . Cl9 Cl 0.7351(12) -0.1585(19) 0.031(2) 0.179(10) Uani 0.206(8) 1 d P . . O1 O 0.60498(17) 0.3006(3) -0.0519(2) 0.0952(8) Uani 1 1 d . . . N1 N 0.59291(18) 0.3274(3) 0.1621(2) 0.0844(7) Uani 1 1 d . . . H1 H 0.5279 0.4221 0.1403 0.101 Uiso 1 1 calc R . . H2 H 0.6255 0.2830 0.2452 0.101 Uiso 1 1 calc R . . C4 C 0.76337(17) 0.0868(3) 0.1193(2) 0.0763(7) Uani 1 1 d . . . C5 C 0.64282(19) 0.2500(3) 0.0679(2) 0.0690(7) Uani 1 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 Cl1 0.0687(7) 0.1139(10) 0.136(4) -0.0025(13) 0.0069(11) -0.0179(6) Cl2 0.134(2) 0.100(2) 0.120(2) -0.0246(15) 0.0364(15) 0.0348(19) Cl3 0.1272(16) 0.0963(13) 0.098(2) 0.0322(13) 0.0354(14) 0.0252(11) Cl4 0.0870(18) 0.173(5) 0.109(6) -0.063(5) -0.022(2) 0.026(2) Cl5 0.160(6) 0.209(9) 0.125(4) 0.033(4) 0.074(4) 0.103(7) Cl6 0.170(3) 0.0764(19) 0.187(10) 0.039(3) 0.033(4) -0.0135(18) Cl7 0.089(3) 0.221(10) 0.230(19) 0.103(12) 0.082(6) 0.026(4) Cl8 0.171(11) 0.199(13) 0.088(5) 0.034(6) 0.024(6) 0.112(11) Cl9 0.179(7) 0.081(4) 0.24(2) -0.073(8) 0.017(8) -0.010(4) O1 0.1021(11) 0.1263(12) 0.0557(16) 0.0064(9) 0.0221(8) 0.0388(9) N1 0.0904(10) 0.1026(12) 0.0603(17) 0.0050(9) 0.0234(8) 0.0247(8) C4 0.0790(10) 0.0714(9) 0.0754(18) -0.0001(8) 0.0192(9) 0.0081(7) C5 0.0749(9) 0.0725(9) 0.059(2) -0.0007(8) 0.0189(9) 0.0066(7) _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 Cl1 Cl7 1.01(2) . ? Cl1 Cl4 1.311(11) . ? Cl1 C4 1.671(3) . ? Cl1 Cl5 1.988(9) . ? Cl1 Cl8 2.199(16) . ? Cl2 Cl9 0.67(2) . ? Cl2 Cl5 1.231(13) . ? Cl2 C4 1.756(4) . ? Cl2 Cl6 1.985(11) . ? Cl2 Cl7 2.32(2) . ? Cl3 Cl8 0.97(2) . ? Cl3 Cl6 1.103(11) . ? Cl3 C4 1.783(3) . ? Cl3 Cl4 2.087(10) . ? Cl3 Cl9 2.32(2) . ? Cl4 Cl8 1.18(2) . ? Cl4 C4 1.821(4) . ? Cl4 Cl7 2.25(2) . ? Cl5 Cl7 1.21(2) . ? Cl5 C4 1.716(5) . ? Cl5 Cl9 1.764(17) . ? Cl6 Cl9 1.38(2) . ? Cl6 C4 1.674(4) . ? Cl6 Cl8 1.893(19) . ? Cl7 C4 1.801(6) . ? Cl8 C4 1.718(6) . ? Cl9 C4 1.681(9) . ? O1 C5 1.213(3) . ? N1 C5 1.321(3) . ? C4 C5 1.554(3) . ? N(1) H(1) 0.860 . ? N(1) H(2) 0.860 . ? 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 Cl7 Cl1 Cl4 150.6(9) . . ? Cl7 Cl1 C4 80.3(7) . . ? Cl4 Cl1 C4 74.2(3) . . ? Cl4 Cl1 Cl5 121.6(4) . . ? C4 Cl1 Cl5 55.1(3) . . ? Cl7 Cl1 Cl8 124.5(8) . . ? C4 Cl1 Cl8 50.5(4) . . ? Cl5 Cl1 Cl8 95.5(5) . . ? Cl9 Cl2 Cl5 134.0(14) . . ? Cl9 Cl2 C4 72.5(10) . . ? Cl5 Cl2 C4 67.5(3) . . ? Cl5 Cl2 Cl6 114.2(3) . . ? C4 Cl2 Cl6 52.8(2) . . ? Cl9 Cl2 Cl7 118.4(12) . . ? C4 Cl2 Cl7 50.1(5) . . ? Cl6 Cl2 Cl7 98.0(5) . . ? Cl8 Cl3 Cl6 131.8(6) . . ? Cl8 Cl3 C4 70.2(4) . . ? Cl6 Cl3 C4 66.1(3) . . ? Cl6 Cl3 Cl4 118.2(4) . . ? C4 Cl3 Cl4 55.5(3) . . ? Cl8 Cl3 Cl9 108.6(5) . . ? C4 Cl3 Cl9 46.1(4) . . ? Cl4 Cl3 Cl9 95.2(4) . . ? Cl8 Cl4 Cl1 124.2(5) . . ? Cl8 Cl4 C4 65.9(4) . . ? Cl1 Cl4 C4 62.0(2) . . ? Cl1 Cl4 Cl3 112.8(2) . . ? C4 Cl4 Cl3 53.8(2) . . ? Cl8 Cl4 Cl7 111.6(6) . . ? C4 Cl4 Cl7 51.3(5) . . ? Cl3 Cl4 Cl7 100.4(5) . . ? Cl7 Cl5 Cl2 144.7(9) . . ? Cl7 Cl5 C4 73.8(6) . . ? Cl2 Cl5 C4 71.0(4) . . ? Cl7 Cl5 Cl9 130.4(7) . . ? C4 Cl5 Cl9 57.7(5) . . ? Cl2 Cl5 Cl1 122.3(4) . . ? C4 Cl5 Cl1 53.01(19) . . ? Cl9 Cl5 Cl1 107.1(6) . . ? Cl3 Cl6 Cl9 138.5(5) . . ? Cl3 Cl6 C4 76.9(3) . . ? Cl9 Cl6 C4 66.0(4) . . ? Cl9 Cl6 Cl8 116.0(5) . . ? C4 Cl6 Cl8 57.2(4) . . ? Cl3 Cl6 Cl2 128.9(3) . . ? C4 Cl6 Cl2 56.6(3) . . ? Cl8 Cl6 Cl2 106.5(5) . . ? Cl1 Cl7 Cl5 127.1(7) . . ? Cl1 Cl7 C4 66.1(4) . . ? Cl5 Cl7 C4 66.2(4) . . ? Cl5 Cl7 Cl4 110.4(6) . . ? C4 Cl7 Cl4 52.0(5) . . ? Cl1 Cl7 Cl2 110.7(5) . . ? C4 Cl7 Cl2 48.4(4) . . ? Cl4 Cl7 Cl2 94.3(3) . . ? Cl3 Cl8 Cl4 153.1(7) . . ? Cl3 Cl8 C4 77.7(6) . . ? Cl4 Cl8 C4 75.4(6) . . ? Cl4 Cl8 Cl6 128.8(5) . . ? C4 Cl8 Cl6 55.0(4) . . ? Cl3 Cl8 Cl1 124.7(5) . . ? C4 Cl8 Cl1 48.6(4) . . ? Cl6 Cl8 Cl1 99.4(3) . . ? Cl2 Cl9 Cl6 149.7(13) . . ? Cl2 Cl9 C4 85.1(9) . . ? Cl6 Cl9 C4 65.5(6) . . ? Cl6 Cl9 Cl5 120.2(7) . . ? C4 Cl9 Cl5 59.7(4) . . ? Cl2 Cl9 Cl3 131.6(12) . . ? C4 Cl9 Cl3 49.8(6) . . ? Cl5 Cl9 Cl3 101.9(5) . . ? C5 C4 Cl1 107.60(15) . . ? C5 C4 Cl6 110.4(2) . . ? Cl1 C4 Cl6 138.4(2) . . ? C5 C4 Cl9 110.8(4) . . ? Cl1 C4 Cl9 128.7(5) . . ? Cl6 C4 Cl9 48.5(8) . . ? C5 C4 Cl5 112.84(19) . . ? Cl1 C4 Cl5 71.9(4) . . ? Cl6 C4 Cl5 107.2(4) . . ? Cl9 C4 Cl5 62.6(7) . . ? C5 C4 Cl8 115.9(2) . . ? Cl1 C4 Cl8 80.9(7) . . ? Cl6 C4 Cl8 67.8(8) . . ? Cl9 C4 Cl8 110.2(7) . . ? Cl5 C4 Cl8 129.3(3) . . ? C5 C4 Cl2 108.61(18) . . ? Cl1 C4 Cl2 112.1(2) . . ? Cl6 C4 Cl2 70.7(4) . . ? Cl8 C4 Cl2 126.9(5) . . ? C5 C4 Cl3 111.34(16) . . ? Cl1 C4 Cl3 111.99(19) . . ? Cl9 C4 Cl3 84.1(9) . . ? Cl5 C4 Cl3 131.6(3) . . ? Cl2 C4 Cl3 105.2(2) . . ? C5 C4 Cl7 106.4(3) . . ? Cl6 C4 Cl7 139.3(5) . . ? Cl9 C4 Cl7 102.0(7) . . ? Cl8 C4 Cl7 110.6(6) . . ? Cl2 C4 Cl7 81.6(9) . . ? Cl3 C4 Cl7 136.7(4) . . ? C5 C4 Cl4 110.5(2) . . ? Cl6 C4 Cl4 105.5(4) . . ? Cl9 C4 Cl4 137.2(5) . . ? Cl5 C4 Cl4 110.1(4) . . ? Cl2 C4 Cl4 139.16(19) . . ? Cl3 C4 Cl4 70.8(4) . . ? Cl7 C4 Cl4 76.7(9) . . ? O1 C5 N1 125.7(2) . . ? O1 C5 C4 118.57(19) . . ? N1 C5 C4 115.7(2) . . ? C(5) N(1) H(1) 120.0 . . ? C(5) N(1) H(2) 120.0 . . ? H(1) N(1) H(2) 120.0 . . ? _diffrn_measured_fraction_theta_max 0.656 _diffrn_reflns_theta_full 30.43 _diffrn_measured_fraction_theta_full 0.656 _refine_diff_density_max 0.152 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.034 # Attachment '- RT.CIF' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 794702' #TrackingRef '- RT.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C2 H2 Cl3 N O' _chemical_formula_sum 'C2 H2 Cl3 N O' _chemical_formula_weight 162.40 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.4368(8) _cell_length_b 5.8004(4) _cell_length_c 10.1922(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.5610(10) _cell_angle_gamma 90.00 _cell_volume 588.26(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.834 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 1.435 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8698 _exptl_absorpt_correction_T_max 0.8698 _exptl_absorpt_process_details 'PROCESS-AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.68933 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator Si(111) _diffrn_measurement_device_type 'IP area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 10 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4028 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 30.43 _reflns_number_total 2485 _reflns_number_gt 2421 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0975P)^2^+0.0337P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.220(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.36(9) _refine_ls_number_reflns 2485 _refine_ls_number_parameters 156 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.007 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 Cl1 Cl 0.75388(8) -0.11163(19) -0.01235(7) 0.0595(3) Uani 1 1 d . . . Cl2 Cl 0.74603(8) -0.14504(19) 0.26578(7) 0.0609(3) Uani 1 1 d . . . Cl3 Cl 0.59015(6) 0.2044(2) 0.08685(8) 0.0635(3) Uani 1 1 d . . . Cl4 Cl 0.6361(4) 0.3945(10) 0.7450(3) 0.0830(14) Uani 0.620(12) 1 d P . . Cl5 Cl 0.6210(3) 0.2972(9) 0.4667(3) 0.0786(13) Uani 0.620(12) 1 d P . . Cl6 Cl 0.7788(3) 0.6745(8) 0.6034(4) 0.0790(10) Uani 0.620(12) 1 d P . . Cl7 Cl 0.6149(7) 0.318(2) 0.7219(10) 0.115(3) Uani 0.380(12) 1 d P . . Cl8 Cl 0.6392(8) 0.358(2) 0.4546(5) 0.115(3) Uani 0.380(12) 1 d P . . Cl9 Cl 0.7678(6) 0.6802(15) 0.6679(15) 0.112(3) Uani 0.380(12) 1 d P . . O1 O 0.88653(18) 0.2954(5) 0.30239(15) 0.0500(7) Uani 1 1 d . . . O2 O 0.90142(19) 0.2075(6) 0.80302(14) 0.0544(7) Uani 1 1 d . . . N1 N 0.9069(2) 0.3172(5) 0.08803(16) 0.0455(7) Uani 1 1 d . . . H1 H 0.9660 0.4252 0.1097 0.055 Uiso 1 1 calc R . . H2 H 0.8808 0.2646 0.0053 0.055 Uiso 1 1 calc R . . N2 N 0.9069(2) 0.1675(6) 0.58483(16) 0.0484(8) Uani 1 1 d . . . H3 H 0.9795 0.0872 0.6092 0.058 Uiso 1 1 calc R . . H4 H 0.8691 0.1982 0.4993 0.058 Uiso 1 1 calc R . . C1 C 0.85583(18) 0.2317(6) 0.18224(17) 0.0376(7) Uani 1 1 d . . . C2 C 0.74307(19) 0.0478(6) 0.13207(18) 0.0392(7) Uani 1 1 d . . . C3 C 0.85333(18) 0.2441(6) 0.67913(17) 0.0362(7) Uani 1 1 d . . . C4 C 0.7246(2) 0.3921(7) 0.62643(19) 0.0424(8) Uani 1 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 Cl1 0.0743(4) 0.0552(9) 0.0511(3) -0.0172(3) 0.0223(3) -0.0123(4) Cl2 0.0743(4) 0.0544(9) 0.0551(3) 0.0166(4) 0.0208(3) -0.0074(4) Cl3 0.0396(2) 0.0708(8) 0.0728(4) 0.0010(4) 0.0059(2) 0.0093(3) Cl4 0.0835(18) 0.123(4) 0.0572(8) 0.0242(12) 0.0434(9) 0.0507(18) Cl5 0.0418(7) 0.114(3) 0.0642(15) -0.0410(18) -0.0081(6) 0.0096(9) Cl6 0.0843(11) 0.045(2) 0.1008(16) 0.0164(15) 0.0175(10) -0.0052(9) Cl7 0.0587(16) 0.185(9) 0.120(4) 0.075(5) 0.055(2) 0.028(3) Cl8 0.101(4) 0.196(9) 0.0330(11) -0.001(2) -0.0006(16) 0.072(4) Cl9 0.085(2) 0.068(5) 0.166(7) -0.020(5) 0.012(3) 0.001(2) O1 0.0586(8) 0.065(2) 0.0272(5) -0.0049(7) 0.0141(5) -0.0164(9) O2 0.0620(9) 0.074(2) 0.0269(5) 0.0032(7) 0.0128(5) 0.0224(11) N1 0.0571(9) 0.053(2) 0.0287(6) -0.0039(8) 0.0161(6) -0.0170(11) N2 0.0499(8) 0.068(2) 0.0288(6) 0.0039(9) 0.0148(6) 0.0106(10) C1 0.0392(7) 0.045(2) 0.0284(6) 0.0009(8) 0.0104(5) -0.0018(9) C2 0.0390(8) 0.043(3) 0.0345(8) 0.0035(9) 0.0092(6) -0.0002(8) C3 0.0413(8) 0.039(2) 0.0287(7) 0.0024(8) 0.0108(6) 0.0020(8) C4 0.0432(8) 0.050(3) 0.0340(7) 0.0022(9) 0.0121(6) -0.0002(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 Cl1 C2 1.771(3) . ? Cl2 C2 1.756(3) . ? Cl3 C2 1.772(3) . ? Cl4 Cl7 0.521(14) . ? Cl4 C4 1.728(3) . ? Cl4 Cl9 2.429(11) . ? Cl5 C4 1.749(3) . ? Cl6 Cl9 0.702(12) . ? Cl6 C4 1.772(5) . ? Cl7 C4 1.766(6) . ? Cl8 C4 1.721(5) . ? Cl9 C4 1.749(9) . ? O1 C1 1.225(2) . ? O2 C3 1.228(2) . ? N1 C1 1.327(3) . ? N2 C3 1.326(3) . ? C1 C2 1.556(4) . ? C3 C4 1.548(4) . ? N(1) H(1) 0.860 . ? N(1) H(2) 0.860 . ? N(2) H(3) 0.860 . ? N(2) H(4) 0.860 . ? 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 Cl7 Cl4 C4 85.5(9) . . ? Cl7 Cl4 Cl9 130.0(9) . . ? Cl9 Cl6 C4 76.7(9) . . ? Cl4 Cl7 C4 77.3(9) . . ? Cl6 Cl9 C4 80.3(8) . . ? Cl6 Cl9 Cl4 122.6(9) . . ? O1 C1 N1 124.7(3) . . ? O1 C1 C2 118.60(18) . . ? N1 C1 C2 116.57(17) . . ? C1 C2 Cl2 110.31(13) . . ? C1 C2 Cl3 105.5(2) . . ? Cl2 C2 Cl3 109.38(11) . . ? C1 C2 Cl1 113.56(13) . . ? Cl2 C2 Cl1 108.8(2) . . ? Cl3 C2 Cl1 109.25(10) . . ? O2 C3 N2 123.8(2) . . ? O2 C3 C4 119.69(19) . . ? N2 C3 C4 116.50(17) . . ? C3 C4 Cl8 114.7(4) . . ? C3 C4 Cl4 110.7(2) . . ? Cl8 C4 Cl4 119.4(3) . . ? C3 C4 Cl9 108.2(3) . . ? Cl8 C4 Cl9 111.9(5) . . ? Cl4 C4 Cl9 88.6(4) . . ? C3 C4 Cl5 112.1(2) . . ? Cl4 C4 Cl5 110.1(2) . . ? Cl9 C4 Cl5 124.6(4) . . ? C3 C4 Cl7 108.2(3) . . ? Cl8 C4 Cl7 108.1(3) . . ? Cl9 C4 Cl7 105.3(4) . . ? Cl5 C4 Cl7 96.6(4) . . ? C3 C4 Cl6 106.3(2) . . ? Cl8 C4 Cl6 93.5(5) . . ? Cl4 C4 Cl6 110.1(3) . . ? Cl5 C4 Cl6 107.4(2) . . ? Cl7 C4 Cl6 125.8(4) . . ? C(1) N(1) H(1) 120.0 . . ? C(1) N(1) H(2) 120.0 . . ? H(1) N(1) H(2) 120.0 . . ? C(3) N(2) H(3) 120.0 . . ? C(3) N(2) H(4) 120.0 . . ? H(3) N(2) H(4) 120.0 . . ? _diffrn_measured_fraction_theta_max 0.701 _diffrn_reflns_theta_full 30.43 _diffrn_measured_fraction_theta_full 0.701 _refine_diff_density_max 0.409 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.087