#------------------------------------------------------------------------------ #$Date: 2022-02-09 12:31:22 +0200 (Wed, 09 Feb 2022) $ #$Revision: 272879 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104559.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_8104559 loop_ _publ_author_name 'Song, Wenqi' 'Yang, Miaoxiu' 'Qian, Liwei' 'Miao, Zongcheng' _publ_section_title ; The crystal structure of 3,3′-[1,4-phenylenebis(methylene)]bis(1-ethenyl-1H-imidazol-3-ium) dichloride -- dichloromethane -- water (1/1/1), C19H24Cl4N4O1 ; _journal_issue 6 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 1175 _journal_page_last 1177 _journal_paper_doi 10.1515/ncrs-2021-0266 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety '2(Cl), C H2 Cl2, H2 O, 2(C9 H10 N2)' _chemical_formula_sum 'C19 H24 Cl4 N4 O' _chemical_formula_weight 466.22 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _cell_angle_alpha 69.805(2) _cell_angle_beta 75.2820(10) _cell_angle_gamma 86.733(2) _cell_formula_units_Z 2 _cell_length_a 8.5930(4) _cell_length_b 12.0814(5) _cell_length_c 12.2430(5) _cell_measurement_reflns_used 5753 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 28.26 _cell_measurement_theta_min 2.67 _cell_volume 1153.07(9) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_unetI/netI 0.0494 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11517 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.289 _diffrn_reflns_theta_min 2.080 _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.530 _exptl_absorpt_correction_T_max 0.948 _exptl_absorpt_correction_T_min 0.938 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1479 before and 0.0617 after correction. The Ratio of minimum to maximum transmission is 0.8522. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.343 _exptl_crystal_description block _exptl_crystal_F_000 484 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.299 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 291 _refine_ls_number_reflns 5737 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0411 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.4397P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0981 _refine_ls_wR_factor_ref 0.1053 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 4737 _reflns_number_total 5737 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file suppl_j_ncrs-2021-0266_suppl.cif _cod_data_source_block a _cod_database_code 8104559 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.949 _shelx_estimated_absorpt_t_min 0.939 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All O(H,H) groups 2. Others Sof(Cl3A)=Sof(Cl4B)=Sof(H19C)=Sof(H19D)=1-FVAR(1) Sof(Cl3B)=Sof(Cl4A)=Sof(H19A)=Sof(H19B)=FVAR(1) 3.a Free rotating group: O1(H1A,H1B) 3.b Secondary CH2 refined with riding coordinates: C19(H19A,H19B), C19(H19C,H19D), C4(H4A,H4B), C13(H13A,H13B) 3.c Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17) ; _shelx_res_file ; TITL a_b.res in P-1 a.res created by SHELXL-2018/3 at 13:55:09 on 16-Apr-2021 REM Old TITL A in P-1 REM SHELXT solution in P-1: R1 0.230, Rweak 0.019, Alpha 0.074 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N5 O4 Cl2 CELL 0.71073 8.593 12.0814 12.243 69.805 75.282 86.733 ZERR 2 0.0004 0.0005 0.0005 0.002 0.001 0.002 LATT 1 SFAC C H Cl N O UNIT 38 48 8 8 2 L.S. 20 PLAN 7 SIZE 0.1 0.12 0.1 TEMP 23 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 acta REM REM " REM WGHT 0.035300 0.439700 FVAR 1.32173 0.44827 CL1 3 0.970605 -0.258978 0.127812 11.00000 0.03778 0.03537 = 0.04163 -0.01071 -0.00801 0.00399 CL2 3 0.500579 -0.239011 0.433711 11.00000 0.02943 0.03804 = 0.02899 -0.01397 -0.00911 0.01018 PART 2 CL3A 3 0.369717 0.363226 0.088905 -21.00000 0.12717 0.06246 = 0.11569 -0.01251 -0.07463 -0.01574 PART 1 CL3B 3 0.427214 0.337858 0.057490 21.00000 0.05878 0.08894 = 0.06559 0.00455 -0.02568 -0.01699 CL4A 3 0.133223 0.223363 0.223113 21.00000 0.06008 0.12080 = 0.05834 -0.03214 0.00336 -0.00796 PART 2 CL4B 3 0.147574 0.161933 0.206407 -21.00000 0.06692 0.10740 = 0.05434 0.00991 -0.01390 -0.01668 PART 0 C19 1 0.285458 0.235161 0.084490 11.00000 0.05298 0.06828 = 0.06072 -0.02754 -0.01858 0.00547 PART 1 AFIX 23 H19A 2 0.334704 0.159534 0.091698 21.00000 -1.20000 H19B 2 0.235082 0.256389 0.017862 21.00000 -1.20000 AFIX 23 PART 2 H19C 2 0.237698 0.257800 0.016443 -21.00000 -1.20000 H19D 2 0.371714 0.182430 0.070633 -21.00000 -1.20000 AFIX 6 PART 0 O1 5 0.680484 -0.424788 0.321143 11.00000 0.03470 0.04185 = 0.07753 -0.03016 -0.00576 0.00480 H1A 2 0.619093 -0.382545 0.355709 11.00000 -1.50000 H1B 2 0.745280 -0.375520 0.262148 11.00000 -1.50000 AFIX 0 N1 4 0.703127 0.083158 0.187695 11.00000 0.03124 0.03499 = 0.03052 -0.01672 -0.01443 0.00604 N2 4 0.695782 0.247612 0.219640 11.00000 0.03824 0.04128 = 0.04258 -0.02626 -0.01858 0.00915 C1 1 0.365722 -0.075428 0.055132 11.00000 0.03848 0.03462 = 0.03060 -0.01180 -0.00649 -0.00715 AFIX 43 H1 2 0.275706 -0.126266 0.092243 11.00000 -1.20000 AFIX 0 C2 1 0.483785 -0.080215 0.114908 11.00000 0.04879 0.03065 = 0.02549 -0.00731 -0.01184 -0.00399 AFIX 43 H2 2 0.472536 -0.134124 0.192244 11.00000 -1.20000 AFIX 0 C3 1 0.618880 -0.005249 0.060445 11.00000 0.03610 0.02833 = 0.02975 -0.01538 -0.01190 0.00365 C4 1 0.742930 -0.005313 0.127831 11.00000 0.03949 0.03611 = 0.04346 -0.02342 -0.01986 0.01190 AFIX 23 H4A 2 0.744816 -0.082873 0.187228 11.00000 -1.20000 H4B 2 0.848726 0.013116 0.072507 11.00000 -1.20000 AFIX 0 C5 1 0.581580 0.070823 0.289924 11.00000 0.04088 0.04642 = 0.02797 -0.01252 -0.00931 0.00369 AFIX 43 H5 2 0.515330 0.004282 0.336127 11.00000 -1.20000 AFIX 0 C6 1 0.577724 0.173616 0.309587 11.00000 0.04510 0.05548 = 0.03210 -0.02404 -0.01150 0.01174 AFIX 43 H6 2 0.508069 0.191633 0.372461 11.00000 -1.20000 AFIX 0 C7 1 0.769506 0.190096 0.146430 11.00000 0.02953 0.03876 = 0.03739 -0.02086 -0.01243 0.00401 AFIX 43 H7 2 0.853296 0.220253 0.078061 11.00000 -1.20000 AFIX 0 C8 1 0.728896 0.366150 0.207655 11.00000 0.05665 0.04548 = 0.07093 -0.03884 -0.02986 0.01121 AFIX 43 H8 2 0.676987 0.393225 0.269655 11.00000 -1.20000 AFIX 0 C9 1 0.825095 0.436225 0.117163 11.00000 0.12097 0.04944 = 0.09369 -0.03859 -0.01728 -0.01079 H9A 2 0.853590 0.510715 0.115071 11.00000 0.10498 H9B 2 0.875158 0.423673 0.040004 11.00000 0.09325 N3 4 0.164490 0.436867 0.394042 11.00000 0.02553 0.02773 = 0.03963 -0.01367 -0.01284 0.00479 N4 4 -0.005473 0.298108 0.517976 11.00000 0.02716 0.02462 = 0.03457 -0.01278 -0.01120 0.00636 C10 1 -0.112557 -0.031799 0.452026 11.00000 0.02812 0.03012 = 0.03906 -0.01193 -0.01392 0.00363 AFIX 43 H10 2 -0.188520 -0.053076 0.419985 11.00000 -1.20000 AFIX 0 C11 1 -0.146639 0.054555 0.504535 11.00000 0.02523 0.02743 = 0.04064 -0.01005 -0.00994 0.00733 AFIX 43 H11 2 -0.245111 0.091061 0.507283 11.00000 -1.20000 AFIX 0 C12 1 -0.034373 0.086880 0.553118 11.00000 0.02855 0.02257 = 0.02946 -0.00599 -0.00683 0.00325 C13 1 -0.070224 0.183268 0.607862 11.00000 0.03504 0.02829 = 0.03257 -0.00995 -0.00722 0.00350 AFIX 23 H13A 2 -0.185692 0.187065 0.637262 11.00000 -1.20000 H13B 2 -0.022283 0.165158 0.675481 11.00000 -1.20000 AFIX 0 C14 1 -0.088276 0.378326 0.444438 11.00000 0.02627 0.03106 = 0.03974 -0.01368 -0.01338 0.00750 AFIX 43 H14 2 -0.197048 0.373253 0.447691 11.00000 -1.20000 AFIX 0 C15 1 0.017407 0.465329 0.367075 11.00000 0.02823 0.02935 = 0.04056 -0.01106 -0.01554 0.00696 AFIX 43 H15 2 -0.004362 0.531778 0.307053 11.00000 -1.20000 AFIX 0 C16 1 0.147189 0.335165 0.485952 11.00000 0.02851 0.02634 = 0.04117 -0.01478 -0.01558 0.00679 AFIX 43 H16 2 0.228148 0.296868 0.521437 11.00000 -1.20000 AFIX 0 C17 1 0.312848 0.503437 0.337109 11.00000 0.02781 0.03550 = 0.05537 -0.01612 -0.01303 0.00136 AFIX 43 H17 2 0.399823 0.479423 0.371019 11.00000 -1.20000 AFIX 0 C18 1 0.332423 0.595652 0.240546 11.00000 0.03996 0.05046 = 0.06495 -0.00620 -0.01369 -0.00754 H18A 2 0.254118 0.621751 0.197775 11.00000 0.06550 H18B 2 0.438102 0.633013 0.207361 11.00000 0.06415 HKLF 4 REM a_b.res in P-1 REM wR2 = 0.1053, GooF = S = 1.028, Restrained GooF = 1.028 for all data REM R1 = 0.0411 for 4737 Fo > 4sig(Fo) and 0.0507 for all 5626 data REM 291 parameters refined using 0 restraints END WGHT 0.0353 0.4397 REM Highest difference peak 0.299, deepest hole -0.389, 1-sigma level 0.045 Q1 1 0.5759 -0.1951 0.4293 11.00000 0.05 0.30 Q2 1 0.1368 0.3000 0.1820 11.00000 0.05 0.26 Q3 1 -0.0735 0.0787 0.5102 11.00000 0.05 0.25 Q4 1 0.6424 0.0243 0.0030 11.00000 0.05 0.24 Q5 1 0.5751 -0.0585 0.0677 11.00000 0.05 0.23 Q6 1 0.6592 -0.0035 0.0941 11.00000 0.05 0.23 Q7 1 0.4097 0.2646 0.0647 11.00000 0.05 0.23 ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.97060(5) -0.25898(4) 0.12781(4) 0.03941(12) Uani 1 1 d . . . . . Cl2 Cl 0.50058(4) -0.23901(3) 0.43371(3) 0.03151(10) Uani 1 1 d . . . . . Cl3A Cl 0.3697(8) 0.3632(2) 0.0889(5) 0.0973(13) Uani 0.552(9) 1 d . . P A 2 Cl3B Cl 0.4272(4) 0.3379(5) 0.0575(3) 0.0767(10) Uani 0.448(9) 1 d . . P A 1 Cl4A Cl 0.1332(3) 0.2234(6) 0.22311(19) 0.0824(10) Uani 0.448(9) 1 d . . P A 1 Cl4B Cl 0.1476(3) 0.1619(5) 0.2064(3) 0.0858(13) Uani 0.552(9) 1 d . . P A 2 C19 C 0.2855(3) 0.2352(2) 0.0845(2) 0.0585(5) Uani 1 1 d . . . . . H19A H 0.334704 0.159534 0.091698 0.070 Uiso 0.448(9) 1 calc R U P A 1 H19B H 0.235082 0.256389 0.017862 0.070 Uiso 0.448(9) 1 calc R U P A 1 H19C H 0.237698 0.257800 0.016443 0.070 Uiso 0.552(9) 1 calc R U P A 2 H19D H 0.371714 0.182430 0.070633 0.070 Uiso 0.552(9) 1 calc R U P A 2 O1 O 0.68048(16) -0.42479(12) 0.32114(15) 0.0505(4) Uani 1 1 d G . . . . H1A H 0.619093 -0.382545 0.355709 0.076 Uiso 1 1 d G U . . . H1B H 0.745280 -0.375520 0.262148 0.076 Uiso 1 1 d G U . . . N1 N 0.70313(16) 0.08316(12) 0.18770(11) 0.0297(3) Uani 1 1 d . . . . . N2 N 0.69578(18) 0.24761(13) 0.21964(13) 0.0362(3) Uani 1 1 d . . . . . C1 C 0.3657(2) -0.07543(15) 0.05513(14) 0.0345(4) Uani 1 1 d . . . . . H1 H 0.275706 -0.126266 0.092243 0.041 Uiso 1 1 calc R U . . . C2 C 0.4838(2) -0.08022(14) 0.11491(14) 0.0349(4) Uani 1 1 d . . . . . H2 H 0.472536 -0.134124 0.192244 0.042 Uiso 1 1 calc R U . . . C3 C 0.6189(2) -0.00525(13) 0.06044(13) 0.0293(3) Uani 1 1 d . . . . . C4 C 0.7429(2) -0.00531(15) 0.12783(16) 0.0357(4) Uani 1 1 d . . . . . H4A H 0.744816 -0.082873 0.187228 0.043 Uiso 1 1 calc R U . . . H4B H 0.848726 0.013116 0.072507 0.043 Uiso 1 1 calc R U . . . C5 C 0.5816(2) 0.07082(17) 0.28992(14) 0.0384(4) Uani 1 1 d . . . . . H5 H 0.515330 0.004282 0.336127 0.046 Uiso 1 1 calc R U . . . C6 C 0.5777(2) 0.17362(17) 0.30959(15) 0.0419(4) Uani 1 1 d . . . . . H6 H 0.508069 0.191633 0.372461 0.050 Uiso 1 1 calc R U . . . C7 C 0.76951(19) 0.19010(15) 0.14643(15) 0.0324(3) Uani 1 1 d . . . . . H7 H 0.853296 0.220253 0.078061 0.039 Uiso 1 1 calc R U . . . C8 C 0.7289(3) 0.36615(18) 0.2077(2) 0.0503(5) Uani 1 1 d . . . . . H8 H 0.676987 0.393225 0.269655 0.060 Uiso 1 1 calc R U . . . C9 C 0.8251(5) 0.4362(3) 0.1172(3) 0.0855(10) Uani 1 1 d . . . . . H9A H 0.854(4) 0.511(3) 0.115(3) 0.105(11) Uiso 1 1 d . . . . . H9B H 0.875(4) 0.424(3) 0.040(3) 0.093(10) Uiso 1 1 d . . . . . N3 N 0.16449(15) 0.43687(11) 0.39404(12) 0.0296(3) Uani 1 1 d . . . . . N4 N -0.00547(15) 0.29811(11) 0.51798(12) 0.0276(3) Uani 1 1 d . . . . . C10 C -0.11256(19) -0.03180(14) 0.45203(15) 0.0315(3) Uani 1 1 d . . . . . H10 H -0.188520 -0.053076 0.419985 0.038 Uiso 1 1 calc R U . . . C11 C -0.14664(19) 0.05456(13) 0.50454(14) 0.0315(3) Uani 1 1 d . . . . . H11 H -0.245111 0.091061 0.507283 0.038 Uiso 1 1 calc R U . . . C12 C -0.03437(18) 0.08688(13) 0.55312(13) 0.0278(3) Uani 1 1 d . . . . . C13 C -0.0702(2) 0.18327(13) 0.60786(14) 0.0324(3) Uani 1 1 d . . . . . H13A H -0.185692 0.187065 0.637262 0.039 Uiso 1 1 calc R U . . . H13B H -0.022283 0.165158 0.675481 0.039 Uiso 1 1 calc R U . . . C14 C -0.08828(19) 0.37833(14) 0.44444(14) 0.0312(3) Uani 1 1 d . . . . . H14 H -0.197048 0.373253 0.447691 0.037 Uiso 1 1 calc R U . . . C15 C 0.01741(19) 0.46533(14) 0.36707(15) 0.0319(3) Uani 1 1 d . . . . . H15 H -0.004362 0.531778 0.307053 0.038 Uiso 1 1 calc R U . . . C16 C 0.14719(19) 0.33517(13) 0.48595(14) 0.0301(3) Uani 1 1 d . . . . . H16 H 0.228148 0.296868 0.521437 0.036 Uiso 1 1 calc R U . . . C17 C 0.3128(2) 0.50344(15) 0.33711(17) 0.0389(4) Uani 1 1 d . . . . . H17 H 0.399823 0.479423 0.371019 0.047 Uiso 1 1 calc R U . . . C18 C 0.3324(3) 0.5957(2) 0.2405(2) 0.0550(5) Uani 1 1 d . . . . . H18A H 0.254(3) 0.622(2) 0.198(2) 0.066(7) Uiso 1 1 d . . . . . H18B H 0.438(3) 0.633(2) 0.207(2) 0.064(7) Uiso 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 0.0378(2) 0.0354(2) 0.0416(2) -0.01071(17) -0.00801(17) 0.00399(16) Cl2 0.02943(18) 0.0380(2) 0.02899(17) -0.01397(15) -0.00911(14) 0.01018(15) Cl3A 0.127(3) 0.0625(10) 0.116(2) -0.0125(11) -0.075(2) -0.0157(14) Cl3B 0.0588(12) 0.089(2) 0.0656(12) 0.0046(11) -0.0257(9) -0.0170(11) Cl4A 0.0601(9) 0.121(3) 0.0583(9) -0.0321(12) 0.0034(7) -0.0080(12) Cl4B 0.0669(9) 0.107(2) 0.0543(10) 0.0099(11) -0.0139(7) -0.0167(11) C19 0.0530(12) 0.0683(14) 0.0607(13) -0.0275(11) -0.0186(10) 0.0055(11) O1 0.0347(7) 0.0418(7) 0.0775(10) -0.0302(7) -0.0058(6) 0.0048(6) N1 0.0312(7) 0.0350(7) 0.0305(6) -0.0167(6) -0.0144(5) 0.0060(5) N2 0.0382(7) 0.0413(8) 0.0426(7) -0.0263(7) -0.0186(6) 0.0091(6) C1 0.0385(9) 0.0346(8) 0.0306(7) -0.0118(7) -0.0065(7) -0.0072(7) C2 0.0488(10) 0.0306(8) 0.0255(7) -0.0073(6) -0.0118(7) -0.0040(7) C3 0.0361(8) 0.0283(7) 0.0298(7) -0.0154(6) -0.0119(6) 0.0037(6) C4 0.0395(9) 0.0361(8) 0.0435(9) -0.0234(7) -0.0199(7) 0.0119(7) C5 0.0409(9) 0.0464(10) 0.0280(7) -0.0125(7) -0.0093(7) 0.0037(8) C6 0.0451(10) 0.0555(11) 0.0321(8) -0.0240(8) -0.0115(7) 0.0117(8) C7 0.0295(7) 0.0388(8) 0.0374(8) -0.0209(7) -0.0124(6) 0.0040(6) C8 0.0567(12) 0.0455(11) 0.0709(13) -0.0388(11) -0.0299(11) 0.0112(9) C9 0.121(3) 0.0494(14) 0.094(2) -0.0386(15) -0.017(2) -0.0108(16) N3 0.0255(6) 0.0277(6) 0.0396(7) -0.0137(6) -0.0128(5) 0.0048(5) N4 0.0272(6) 0.0246(6) 0.0346(6) -0.0128(5) -0.0112(5) 0.0064(5) C10 0.0281(7) 0.0301(7) 0.0391(8) -0.0119(7) -0.0139(6) 0.0036(6) C11 0.0252(7) 0.0274(7) 0.0406(8) -0.0101(6) -0.0099(6) 0.0073(6) C12 0.0285(7) 0.0226(7) 0.0295(7) -0.0060(6) -0.0068(6) 0.0033(6) C13 0.0350(8) 0.0283(7) 0.0326(7) -0.0100(6) -0.0072(6) 0.0035(6) C14 0.0263(7) 0.0311(8) 0.0397(8) -0.0137(7) -0.0134(6) 0.0075(6) C15 0.0282(7) 0.0293(7) 0.0406(8) -0.0111(7) -0.0155(6) 0.0070(6) C16 0.0285(7) 0.0263(7) 0.0412(8) -0.0148(6) -0.0156(6) 0.0068(6) C17 0.0278(8) 0.0355(9) 0.0554(10) -0.0161(8) -0.0130(7) 0.0014(7) C18 0.0400(11) 0.0505(12) 0.0650(13) -0.0062(10) -0.0137(10) -0.0075(9) 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' Cl Cl 0.1484 0.1585 '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' 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 Cl3A C19 H19C 108.4 . . Cl3A C19 H19D 108.4 . . Cl3B C19 Cl4A 110.13(18) . . Cl3B C19 H19A 109.6 . . Cl3B C19 H19B 109.6 . . Cl4A C19 H19A 109.6 . . Cl4A C19 H19B 109.6 . . Cl4B C19 Cl3A 115.32(18) . . Cl4B C19 H19C 108.4 . . Cl4B C19 H19D 108.4 . . H19A C19 H19B 108.1 . . H19C C19 H19D 107.5 . . H1A O1 H1B 104.5 . . C5 N1 C4 125.34(14) . . C7 N1 C4 125.09(14) . . C7 N1 C5 109.36(14) . . C6 N2 C8 124.79(15) . . C7 N2 C6 108.40(14) . . C7 N2 C8 126.80(16) . . C2 C1 H1 119.9 . . C2 C1 C3 120.20(15) . 2_655 C3 C1 H1 119.9 2_655 . C1 C2 H2 119.8 . . C1 C2 C3 120.49(15) . . C3 C2 H2 119.8 . . C1 C3 C4 119.95(15) 2_655 . C2 C3 C1 119.31(15) . 2_655 C2 C3 C4 120.62(15) . . N1 C4 C3 109.38(13) . . N1 C4 H4A 109.8 . . N1 C4 H4B 109.8 . . C3 C4 H4A 109.8 . . C3 C4 H4B 109.8 . . H4A C4 H4B 108.2 . . N1 C5 H5 126.7 . . C6 C5 N1 106.54(16) . . C6 C5 H5 126.7 . . N2 C6 H6 126.3 . . C5 C6 N2 107.49(15) . . C5 C6 H6 126.3 . . N1 C7 N2 108.21(14) . . N1 C7 H7 125.9 . . N2 C7 H7 125.9 . . N2 C8 H8 118.3 . . C9 C8 N2 123.4(2) . . C9 C8 H8 118.3 . . C8 C9 H9A 122(2) . . C8 C9 H9B 126.7(17) . . H9A C9 H9B 112(3) . . C15 N3 C17 127.31(14) . . C16 N3 C15 108.86(13) . . C16 N3 C17 123.82(14) . . C14 N4 C13 125.76(13) . . C16 N4 C13 125.00(13) . . C16 N4 C14 108.88(13) . . C11 C10 H10 119.8 . . C11 C10 C12 120.50(15) . 2_556 C12 C10 H10 119.8 2_556 . C10 C11 H11 119.8 . . C10 C11 C12 120.32(14) . . C12 C11 H11 119.8 . . C10 C12 C13 120.54(14) 2_556 . C11 C12 C10 119.18(14) . 2_556 C11 C12 C13 120.26(14) . . N4 C13 C12 110.44(12) . . N4 C13 H13A 109.6 . . N4 C13 H13B 109.6 . . C12 C13 H13A 109.6 . . C12 C13 H13B 109.6 . . H13A C13 H13B 108.1 . . N4 C14 H14 126.3 . . C15 C14 N4 107.33(14) . . C15 C14 H14 126.3 . . N3 C15 H15 126.6 . . C14 C15 N3 106.75(14) . . C14 C15 H15 126.6 . . N3 C16 H16 125.9 . . N4 C16 N3 108.18(14) . . N4 C16 H16 125.9 . . N3 C17 H17 118.4 . . C18 C17 N3 123.27(18) . . C18 C17 H17 118.4 . . C17 C18 H18A 123.6(15) . . C17 C18 H18B 117.1(15) . . H18A C18 H18B 119(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl3A C19 1.768(3) . Cl3B C19 1.678(5) . Cl4A C19 1.827(3) . Cl4B C19 1.650(3) . C19 H19A 0.9700 . C19 H19B 0.9700 . C19 H19C 0.9700 . C19 H19D 0.9700 . O1 H1A 0.8502 . O1 H1B 0.8501 . N1 C4 1.4726(19) . N1 C5 1.380(2) . N1 C7 1.318(2) . N2 C6 1.377(2) . N2 C7 1.334(2) . N2 C8 1.426(2) . C1 H1 0.9300 . C1 C2 1.382(2) . C1 C3 1.392(2) 2_655 C2 H2 0.9300 . C2 C3 1.386(2) . C3 C4 1.504(2) . C4 H4A 0.9700 . C4 H4B 0.9700 . C5 H5 0.9300 . C5 C6 1.341(3) . C6 H6 0.9300 . C7 H7 0.9300 . C8 H8 0.9300 . C8 C9 1.263(4) . C9 H9A 0.94(3) . C9 H9B 0.99(3) . N3 C15 1.382(2) . N3 C16 1.334(2) . N3 C17 1.427(2) . N4 C13 1.472(2) . N4 C14 1.379(2) . N4 C16 1.3264(19) . C10 H10 0.9300 . C10 C11 1.386(2) . C10 C12 1.391(2) 2_556 C11 H11 0.9300 . C11 C12 1.390(2) . C12 C13 1.514(2) . C13 H13A 0.9700 . C13 H13B 0.9700 . C14 H14 0.9300 . C14 C15 1.346(2) . C15 H15 0.9300 . C16 H16 0.9300 . C17 H17 0.9300 . C17 C18 1.295(3) . C18 H18A 0.93(3) . C18 H18B 0.96(2) . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C5 C6 N2 0.2(2) . . . . C1 C2 C3 C1 0.3(3) . . . 2_655 C1 C2 C3 C4 176.43(15) . . . . C1 C3 C4 N1 84.51(18) 2_655 . . . C2 C3 C4 N1 -91.64(18) . . . . C3 C1 C2 C3 -0.3(3) 2_655 . . . C4 N1 C5 C6 -175.46(15) . . . . C4 N1 C7 N2 175.61(14) . . . . C5 N1 C4 C3 75.1(2) . . . . C5 N1 C7 N2 0.65(19) . . . . C6 N2 C7 N1 -0.53(19) . . . . C6 N2 C8 C9 -171.7(3) . . . . C7 N1 C4 C3 -99.07(18) . . . . C7 N1 C5 C6 -0.5(2) . . . . C7 N2 C6 C5 0.2(2) . . . . C7 N2 C8 C9 7.0(4) . . . . C8 N2 C6 C5 179.09(17) . . . . C8 N2 C7 N1 -179.38(16) . . . . N4 C14 C15 N3 0.25(17) . . . . C10 C11 C12 C10 0.2(3) . . . 2_556 C10 C11 C12 C13 178.57(14) . . . . C10 C12 C13 N4 84.75(18) 2_556 . . . C11 C12 C13 N4 -93.58(17) . . . . C12 C10 C11 C12 -0.2(3) 2_556 . . . C13 N4 C14 C15 -173.55(14) . . . . C13 N4 C16 N3 173.47(13) . . . . C14 N4 C13 C12 92.37(18) . . . . C14 N4 C16 N3 0.04(17) . . . . C15 N3 C16 N4 0.12(17) . . . . C15 N3 C17 C18 -8.4(3) . . . . C16 N3 C15 C14 -0.24(18) . . . . C16 N3 C17 C18 172.82(19) . . . . C16 N4 C13 C12 -79.96(18) . . . . C16 N4 C14 C15 -0.18(17) . . . . C17 N3 C15 C14 -179.15(15) . . . . C17 N3 C16 N4 179.08(14) . . . .