#------------------------------------------------------------------------------ #$Date: 2026-06-17 23:23:21 +0100 (Wed, 17 Jun 2026) $ #$Revision: 306586 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577402.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_1577402 loop_ _publ_author_name 'Hogan, David Thomas' 'Krappe, Alexander R.' 'Feyerherm, R.' 'Weber, Manuela' 'Resch-Genger, Ute' 'Eigler, Siegfried' _publ_section_title ; Large Stokes shift fluorophores from meta-substituted zwitterions ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03405E _journal_year 2026 _chemical_absolute_configuration rm _chemical_formula_sum 'C19 H16 Cl2 N4' _chemical_formula_weight 371.26 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-10-08 deposited with the CCDC. 2026-06-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6087(4) _cell_length_b 12.6810(8) _cell_length_c 18.7415(11) _cell_measurement_reflns_used 3337 _cell_measurement_temperature 149(2) _cell_measurement_theta_max 66.50 _cell_measurement_theta_min 4.21 _cell_volume 1808.29(18) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX4' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 149(2) _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_device_type 'Bruker Photon CMOS Detector, D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_unetI/netI 0.0857 _diffrn_reflns_Laue_measured_fraction_full 0.969 _diffrn_reflns_Laue_measured_fraction_max 0.969 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 11063 _diffrn_reflns_point_group_measured_fraction_full 0.951 _diffrn_reflns_point_group_measured_fraction_max 0.951 _diffrn_reflns_theta_full 66.730 _diffrn_reflns_theta_max 66.730 _diffrn_reflns_theta_min 4.209 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 3.294 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description needle _exptl_crystal_F_000 768 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.620 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.030 _exptl_transmission_factor_max 0.5913 _exptl_transmission_factor_min 0.2859 _refine_diff_density_max 0.309 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.070 _refine_ls_abs_structure_details ; Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.078(14) _refine_ls_extinction_coef 0.0028(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3052 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0827 _refine_ls_R_factor_gt 0.0515 _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^)+(0.0552P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1111 _refine_ls_wR_factor_ref 0.1234 _reflns_Friedel_coverage 0.696 _reflns_Friedel_fraction_full 0.927 _reflns_Friedel_fraction_max 0.927 _reflns_number_gt 2177 _reflns_number_total 3052 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03405e2.cif _cod_data_source_block 0751DH _cod_database_code 1577402 _shelx_shelxl_version_number 2019/3 _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_min 0.235 _shelx_estimated_absorpt_t_max 0.908 _shelx_res_file ; TITL fast2_a.res in P2(1)2(1)2(1) 0751DH.res created by SHELXL-2019/3 at 08:35:42 on 18-Jun-2025 REM Old TITL fast2 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.122, Rweak 0.026, Alpha 0.005 REM 0.190 for 12 systematic absences, Orientation as input REM Flack x = 0.128 ( 0.034 ) from 287 Parsons' quotients REM Formula found by SHELXT: C19 Cl2 N4 CELL 1.54178 7.6087 12.681 18.7415 90 90 90 ZERR 4 0.0004 0.0008 0.0011 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H Cl N UNIT 76 64 8 16 L.S. 30 PLAN 2 SIZE 0.03 0.05 0.62 TEMP -124.35 CONF BOND $H htab LIST 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.055200 EXTI 0.002751 FVAR 0.52492 CL1 3 0.330163 0.628974 0.433381 11.00000 0.04997 0.05604 = 0.06202 -0.01121 0.00239 -0.00821 CL2 3 0.608547 0.597063 0.537870 11.00000 0.07905 0.06794 = 0.07185 0.00140 -0.01115 0.01957 C19 1 0.454899 0.687399 0.502502 11.00000 0.05475 0.04252 = 0.04147 0.00010 0.00473 0.00569 AFIX 23 H19A 2 0.517763 0.749815 0.483648 11.00000 -1.20000 H19B 2 0.375112 0.711449 0.540925 11.00000 -1.20000 AFIX 0 N1 4 0.276415 0.105848 0.679480 11.00000 0.03009 0.02883 = 0.02557 0.00049 0.00413 0.00544 N2 4 0.403064 0.258583 0.677660 11.00000 0.02514 0.02716 = 0.02730 -0.00061 0.00483 0.00307 N3 4 0.135266 0.520775 0.299217 11.00000 0.04990 0.03911 = 0.03083 0.00736 0.00247 0.00432 N4 4 0.345200 0.318842 0.127797 11.00000 0.06318 0.05269 = 0.03163 0.00247 -0.00046 0.00779 C1 1 0.351708 0.237798 0.511438 11.00000 0.02245 0.02652 = 0.02274 0.00326 0.00044 0.00023 AFIX 43 H1 2 0.299147 0.301839 0.526815 11.00000 -1.20000 AFIX 0 C2 1 0.388251 0.222970 0.437878 11.00000 0.01944 0.02297 = 0.02699 0.00261 0.00100 -0.00084 C3 1 0.462899 0.125132 0.415339 11.00000 0.02113 0.02606 = 0.02895 -0.00036 0.00210 0.00083 C4 1 0.502757 0.048307 0.467023 11.00000 0.02531 0.02815 = 0.02941 0.00064 0.00320 0.00144 AFIX 43 H4 2 0.553754 -0.016623 0.452509 11.00000 -1.20000 AFIX 0 C5 1 0.469335 0.065463 0.537915 11.00000 0.02444 0.03061 = 0.02784 0.00566 0.00100 0.00388 AFIX 43 H5 2 0.498791 0.012922 0.572012 11.00000 -1.20000 AFIX 0 C6 1 0.390817 0.161453 0.560744 11.00000 0.02184 0.02938 = 0.02379 -0.00057 0.00240 0.00095 C7 1 0.354717 0.176486 0.636325 11.00000 0.02432 0.02051 = 0.02084 0.00217 0.00177 0.00003 C8 1 0.280239 0.143520 0.748968 11.00000 0.03121 0.04389 = 0.02161 0.00378 0.00515 0.00479 AFIX 43 H8 2 0.235818 0.108557 0.790011 11.00000 -1.20000 AFIX 0 C9 1 0.358432 0.238685 0.747544 11.00000 0.03272 0.04406 = 0.01911 0.00032 0.00040 0.00755 AFIX 43 H9 2 0.378936 0.283610 0.787245 11.00000 -1.20000 AFIX 0 C10 1 0.344969 0.300614 0.386815 11.00000 0.02609 0.02552 = 0.02640 0.00193 -0.00475 -0.00237 AFIX 43 H10 2 0.298030 0.366196 0.402215 11.00000 -1.20000 AFIX 0 C11 1 0.370040 0.282534 0.314161 11.00000 0.02726 0.02695 = 0.02426 0.00155 -0.00224 0.00119 C12 1 0.450162 0.186204 0.293258 11.00000 0.02825 0.03541 = 0.02678 -0.00087 0.00238 -0.00696 AFIX 43 H12 2 0.473634 0.174043 0.244156 11.00000 -1.20000 AFIX 0 C13 1 0.494175 0.110845 0.341834 11.00000 0.03496 0.03161 = 0.02547 -0.00088 0.00046 -0.00081 AFIX 43 H13 2 0.547118 0.047250 0.325839 11.00000 -1.20000 AFIX 0 C14 1 0.312584 0.357286 0.260682 11.00000 0.03102 0.03189 = 0.02191 0.00155 -0.00039 -0.00041 C15 1 0.214749 0.448079 0.280428 11.00000 0.02696 0.03771 = 0.02488 0.01016 -0.00478 -0.00336 C16 1 0.330054 0.336362 0.187241 11.00000 0.03531 0.03496 = 0.02963 0.00371 -0.00199 -0.00285 C17 1 0.486816 0.357426 0.652562 11.00000 0.03083 0.02885 = 0.03202 -0.00231 0.00350 -0.00524 AFIX 137 H17A 2 0.567098 0.383811 0.689349 11.00000 -1.50000 H17B 2 0.395934 0.410369 0.643091 11.00000 -1.50000 H17C 2 0.552772 0.343429 0.608658 11.00000 -1.50000 AFIX 0 C18 1 0.194298 0.005840 0.657981 11.00000 0.03983 0.02720 = 0.03809 0.00434 0.00585 -0.01178 AFIX 137 H18A 2 0.082684 -0.002958 0.683388 11.00000 -1.50000 H18B 2 0.272971 -0.052815 0.669774 11.00000 -1.50000 H18C 2 0.172497 0.006621 0.606448 11.00000 -1.50000 REM REM 0751DH.hkl REM AFIX 0 HKLF 4 REM fast2_a.res in P2(1)2(1)2(1) REM wR2 = 0.1234, GooF = S = 1.037, Restrained GooF = 1.037 for all data REM R1 = 0.0515 for 2177 Fo > 4sig(Fo) and 0.0827 for all 3052 data REM 229 parameters refined using 0 restraints END WGHT 0.0566 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y+1/2, -z+1/2 HTAB C19 N4_$1 EQIV $2 -x+1/2, -y+1, z+1/2 HTAB C19 N4_$2 HTAB C9 N3_$2 REM Highest difference peak 0.309, deepest hole -0.348, 1-sigma level 0.070 Q1 1 0.6613 0.5942 0.4584 11.00000 0.05 0.31 Q2 1 0.3945 0.3355 0.7794 11.00000 0.05 0.31 ; _shelx_res_checksum 71080 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 0.3302(2) 0.62897(13) 0.43338(9) 0.0560(5) Uani 1 1 d . . . . . Cl2 Cl 0.6085(3) 0.59706(15) 0.53787(10) 0.0729(7) Uani 1 1 d . . . . . C19 C 0.4549(10) 0.6874(5) 0.5025(3) 0.0462(17) Uani 1 1 d . . . . . H19A H 0.517763 0.749815 0.483648 0.055 Uiso 1 1 calc R U . . . H19B H 0.375112 0.711449 0.540925 0.055 Uiso 1 1 calc R U . . . N1 N 0.2764(6) 0.1058(3) 0.6795(2) 0.0282(11) Uani 1 1 d . . . . . N2 N 0.4031(6) 0.2586(3) 0.6777(2) 0.0265(11) Uani 1 1 d . . . . . N3 N 0.1353(7) 0.5208(4) 0.2992(2) 0.0399(13) Uani 1 1 d . . . . . N4 N 0.3452(8) 0.3188(4) 0.1278(3) 0.0492(15) Uani 1 1 d . . . . . C1 C 0.3517(8) 0.2378(4) 0.5114(2) 0.0239(12) Uani 1 1 d . . . . . H1 H 0.299147 0.301839 0.526815 0.029 Uiso 1 1 calc R U . . . C2 C 0.3883(7) 0.2230(3) 0.4379(3) 0.0231(12) Uani 1 1 d . . . . . C3 C 0.4629(7) 0.1251(4) 0.4153(3) 0.0254(12) Uani 1 1 d . . . . . C4 C 0.5028(7) 0.0483(4) 0.4670(3) 0.0276(13) Uani 1 1 d . . . . . H4 H 0.553754 -0.016623 0.452509 0.033 Uiso 1 1 calc R U . . . C5 C 0.4693(7) 0.0655(4) 0.5379(3) 0.0276(13) Uani 1 1 d . . . . . H5 H 0.498791 0.012922 0.572012 0.033 Uiso 1 1 calc R U . . . C6 C 0.3908(7) 0.1615(4) 0.5607(3) 0.0250(12) Uani 1 1 d . . . . . C7 C 0.3547(7) 0.1765(3) 0.6363(2) 0.0219(12) Uani 1 1 d . . . . . C8 C 0.2802(8) 0.1435(4) 0.7490(3) 0.0322(14) Uani 1 1 d . . . . . H8 H 0.235818 0.108557 0.790011 0.039 Uiso 1 1 calc R U . . . C9 C 0.3584(8) 0.2387(4) 0.7475(3) 0.0320(14) Uani 1 1 d . . . . . H9 H 0.378936 0.283610 0.787245 0.038 Uiso 1 1 calc R U . . . C10 C 0.3450(7) 0.3006(4) 0.3868(3) 0.0260(13) Uani 1 1 d . . . . . H10 H 0.298030 0.366196 0.402215 0.031 Uiso 1 1 calc R U . . . C11 C 0.3700(8) 0.2825(4) 0.3142(3) 0.0262(13) Uani 1 1 d . . . . . C12 C 0.4502(8) 0.1862(4) 0.2933(3) 0.0301(14) Uani 1 1 d . . . . . H12 H 0.473634 0.174043 0.244156 0.036 Uiso 1 1 calc R U . . . C13 C 0.4942(8) 0.1108(4) 0.3418(3) 0.0307(14) Uani 1 1 d . . . . . H13 H 0.547118 0.047250 0.325839 0.037 Uiso 1 1 calc R U . . . C14 C 0.3126(8) 0.3573(4) 0.2607(3) 0.0283(13) Uani 1 1 d . . . . . C15 C 0.2147(8) 0.4481(4) 0.2804(3) 0.0298(14) Uani 1 1 d . . . . . C16 C 0.3301(8) 0.3364(4) 0.1872(3) 0.0333(14) Uani 1 1 d . . . . . C17 C 0.4868(8) 0.3574(4) 0.6526(3) 0.0306(14) Uani 1 1 d . . . . . H17A H 0.567098 0.383811 0.689349 0.046 Uiso 1 1 calc R U . . . H17B H 0.395934 0.410369 0.643091 0.046 Uiso 1 1 calc R U . . . H17C H 0.552772 0.343429 0.608658 0.046 Uiso 1 1 calc R U . . . C18 C 0.1943(8) 0.0058(4) 0.6580(3) 0.0350(15) Uani 1 1 d . . . . . H18A H 0.082684 -0.002958 0.683388 0.053 Uiso 1 1 calc R U . . . H18B H 0.272971 -0.052815 0.669774 0.053 Uiso 1 1 calc R U . . . H18C H 0.172497 0.006621 0.606448 0.053 Uiso 1 1 calc R U . . . 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 0.0500(12) 0.0560(9) 0.0620(11) -0.0112(8) 0.0024(9) -0.0082(9) Cl2 0.0790(17) 0.0679(11) 0.0719(13) 0.0014(9) -0.0112(11) 0.0196(11) C19 0.055(5) 0.043(3) 0.041(4) 0.000(3) 0.005(4) 0.006(3) N1 0.030(3) 0.029(2) 0.026(2) 0.0005(19) 0.004(2) 0.005(2) N2 0.025(3) 0.027(2) 0.027(2) -0.0006(19) 0.005(2) 0.003(2) N3 0.050(4) 0.039(3) 0.031(3) 0.007(2) 0.002(3) 0.004(3) N4 0.063(4) 0.053(3) 0.032(3) 0.002(2) 0.000(3) 0.008(3) C1 0.022(3) 0.027(2) 0.023(3) 0.003(2) 0.000(2) 0.000(2) C2 0.019(3) 0.023(2) 0.027(3) 0.003(2) 0.001(3) -0.001(2) C3 0.021(3) 0.026(2) 0.029(3) 0.000(2) 0.002(2) 0.001(2) C4 0.025(4) 0.028(3) 0.029(3) 0.001(2) 0.003(3) 0.001(2) C5 0.024(4) 0.031(3) 0.028(3) 0.006(2) 0.001(3) 0.004(2) C6 0.022(3) 0.029(2) 0.024(3) -0.001(2) 0.002(2) 0.001(2) C7 0.024(3) 0.021(2) 0.021(3) 0.0022(19) 0.002(3) 0.000(2) C8 0.031(4) 0.044(3) 0.022(3) 0.004(2) 0.005(3) 0.005(3) C9 0.033(4) 0.044(3) 0.019(3) 0.000(2) 0.000(3) 0.008(3) C10 0.026(4) 0.026(2) 0.026(3) 0.002(2) -0.005(3) -0.002(3) C11 0.027(4) 0.027(3) 0.024(3) 0.002(2) -0.002(3) 0.001(3) C12 0.028(4) 0.035(3) 0.027(3) -0.001(2) 0.002(3) -0.007(3) C13 0.035(4) 0.032(3) 0.025(3) -0.001(2) 0.000(3) -0.001(3) C14 0.031(4) 0.032(3) 0.022(3) 0.002(2) 0.000(3) 0.000(3) C15 0.027(4) 0.038(3) 0.025(3) 0.010(2) -0.005(3) -0.003(3) C16 0.035(4) 0.035(3) 0.030(3) 0.004(2) -0.002(3) -0.003(3) C17 0.031(4) 0.029(3) 0.032(3) -0.002(2) 0.004(3) -0.005(3) C18 0.040(4) 0.027(3) 0.038(3) 0.004(2) 0.006(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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 '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 _geom_angle_publ_flag Cl2 C19 Cl1 111.0(3) . . ? Cl2 C19 H19A 109.4 . . ? Cl1 C19 H19A 109.4 . . ? Cl2 C19 H19B 109.4 . . ? Cl1 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C7 N1 C8 109.0(4) . . ? C7 N1 C18 126.7(4) . . ? C8 N1 C18 124.3(4) . . ? C7 N2 C9 109.7(4) . . ? C7 N2 C17 126.0(4) . . ? C9 N2 C17 124.3(4) . . ? C6 C1 C2 121.2(5) . . ? C6 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C10 C2 C1 121.4(4) . . ? C10 C2 C3 119.9(4) . . ? C1 C2 C3 118.7(4) . . ? C4 C3 C13 123.2(4) . . ? C4 C3 C2 118.9(4) . . ? C13 C3 C2 117.9(4) . . ? C5 C4 C3 121.2(5) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.4(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.5(5) . . ? C1 C6 C7 121.5(4) . . ? C5 C6 C7 119.0(4) . . ? N1 C7 N2 106.8(4) . . ? N1 C7 C6 125.5(4) . . ? N2 C7 C6 127.5(4) . . ? C9 C8 N1 107.4(5) . . ? C9 C8 H8 126.3 . . ? N1 C8 H8 126.3 . . ? C8 C9 N2 107.0(5) . . ? C8 C9 H9 126.5 . . ? N2 C9 H9 126.5 . . ? C11 C10 C2 121.0(4) . . ? C11 C10 H10 119.5 . . ? C2 C10 H10 119.5 . . ? C10 C11 C12 118.0(4) . . ? C10 C11 C14 121.8(4) . . ? C12 C11 C14 120.1(4) . . ? C13 C12 C11 121.7(5) . . ? C13 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? C12 C13 C3 121.4(5) . . ? C12 C13 H13 119.3 . . ? C3 C13 H13 119.3 . . ? C16 C14 C15 117.2(5) . . ? C16 C14 C11 121.7(5) . . ? C15 C14 C11 120.6(4) . . ? N3 C15 C14 177.4(6) . . ? N4 C16 C14 179.5(7) . . ? N2 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C19 1.769(7) . ? Cl2 C19 1.766(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? N1 C7 1.346(6) . ? N1 C8 1.387(6) . ? N1 C18 1.470(6) . ? N2 C7 1.349(6) . ? N2 C9 1.376(6) . ? N2 C17 1.483(6) . ? N3 C15 1.157(7) . ? N4 C16 1.142(7) . ? C1 C6 1.371(6) . ? C1 C2 1.419(7) . ? C1 H1 0.9500 . ? C2 C10 1.412(6) . ? C2 C3 1.428(7) . ? C3 C4 1.407(7) . ? C3 C13 1.410(7) . ? C4 C5 1.370(7) . ? C4 H4 0.9500 . ? C5 C6 1.422(7) . ? C5 H5 0.9500 . ? C6 C7 1.455(7) . ? C8 C9 1.346(8) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.394(7) . ? C10 H10 0.9500 . ? C11 C12 1.420(7) . ? C11 C14 1.447(7) . ? C12 C13 1.362(7) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C16 1.408(7) . ? C14 C15 1.420(8) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 _geom_torsion_publ_flag C6 C1 C2 C10 178.7(5) . . . . ? C6 C1 C2 C3 1.7(8) . . . . ? C10 C2 C3 C4 -179.1(5) . . . . ? C1 C2 C3 C4 -2.0(7) . . . . ? C10 C2 C3 C13 1.3(8) . . . . ? C1 C2 C3 C13 178.4(5) . . . . ? C13 C3 C4 C5 -179.7(6) . . . . ? C2 C3 C4 C5 0.8(8) . . . . ? C3 C4 C5 C6 0.9(9) . . . . ? C2 C1 C6 C5 -0.1(8) . . . . ? C2 C1 C6 C7 179.6(5) . . . . ? C4 C5 C6 C1 -1.2(8) . . . . ? C4 C5 C6 C7 179.1(5) . . . . ? C8 N1 C7 N2 -1.5(6) . . . . ? C18 N1 C7 N2 176.8(5) . . . . ? C8 N1 C7 C6 174.2(5) . . . . ? C18 N1 C7 C6 -7.5(9) . . . . ? C9 N2 C7 N1 1.3(6) . . . . ? C17 N2 C7 N1 -177.0(5) . . . . ? C9 N2 C7 C6 -174.3(5) . . . . ? C17 N2 C7 C6 7.4(9) . . . . ? C1 C6 C7 N1 133.2(6) . . . . ? C5 C6 C7 N1 -47.1(8) . . . . ? C1 C6 C7 N2 -52.0(8) . . . . ? C5 C6 C7 N2 127.7(6) . . . . ? C7 N1 C8 C9 1.2(6) . . . . ? C18 N1 C8 C9 -177.2(5) . . . . ? N1 C8 C9 N2 -0.4(6) . . . . ? C7 N2 C9 C8 -0.6(7) . . . . ? C17 N2 C9 C8 177.8(5) . . . . ? C1 C2 C10 C11 -175.5(5) . . . . ? C3 C2 C10 C11 1.5(8) . . . . ? C2 C10 C11 C12 -3.7(8) . . . . ? C2 C10 C11 C14 174.6(5) . . . . ? C10 C11 C12 C13 3.1(9) . . . . ? C14 C11 C12 C13 -175.2(5) . . . . ? C11 C12 C13 C3 -0.3(9) . . . . ? C4 C3 C13 C12 178.5(5) . . . . ? C2 C3 C13 C12 -1.9(8) . . . . ? C10 C11 C14 C16 -176.7(6) . . . . ? C12 C11 C14 C16 1.5(9) . . . . ? C10 C11 C14 C15 -5.4(8) . . . . ? C12 C11 C14 C15 172.8(5) . . . . ?