#------------------------------------------------------------------------------ #$Date: 2019-10-15 12:04:36 +0300 (Tue, 15 Oct 2019) $ #$Revision: 219367 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/46/7234646.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_7234646 loop_ _publ_author_name 'Chiara Botta' 'Sara Benedini' 'Lucia Carlucci' 'Alessandra Forni' 'Daniele Marinotto' 'Andrea Nitti' 'Dario Pasini' 'Stefania Righetto' 'Elena Cariati' _publ_section_title ; Polymorphism-dependent aggregation induced emission of a push-pull dye and its multi-stimuli responsive behavior ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 2979 _journal_page_last 2989 _journal_paper_doi 10.1039/C5TC03352G _journal_volume 4 _journal_year 2016 _chemical_formula_moiety 'C20 H20 N4, C H2 Cl2' _chemical_formula_sum 'C21 H22 Cl2 N4' _chemical_formula_weight 401.33 _chemical_name_common 2-(bis(4-dimethylaminophenyl)methylene)malonitrile _chemical_name_systematic '1,1-Dicyano-2,2-bis(4-dimethylaminophenyl)ethylene dichloromethane solvate' _chemical_properties_physical 'The crystals decay in few days owing to co-crystallized solvent loss' _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 105.3500(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.5444(8) _cell_length_b 22.3085(14) _cell_length_c 7.5898(5) _cell_measurement_reflns_used 4027 _cell_measurement_temperature 180(2) _cell_measurement_theta_max 21.834 _cell_measurement_theta_min 2.483 _cell_volume 2048.2(2) _computing_cell_refinement 'SAINT (Bruker, 1997)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP III ( Burnett&Johnson, 1996)' _computing_publication_material 'SHELXL-97,PARST (Nardelli, 1995)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 180(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker Apex II CCD area detector' _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 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 23624 _diffrn_reflns_theta_full 23.41 _diffrn_reflns_theta_max 23.41 _diffrn_reflns_theta_min 1.68 _diffrn_standards_decay_% 0.0 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_correction_T_min 0.593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 840 _exptl_crystal_preparation Luminescent _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane/hexane' _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.487 _refine_diff_density_min -0.747 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 248 _refine_ls_number_reflns 2993 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0541 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+2.7655P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1253 _refine_ls_wR_factor_ref 0.1360 _reflns_number_gt 2360 _reflns_number_total 2993 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL eca10lt in P2(1)/c CELL 0.71073 12.5444 22.3085 7.5898 90.000 105.350 90.000 ZERR 4.00 0.0008 0.0014 0.0005 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N Cl UNIT 84 88 16 8 L.S. 4 ACTA BOND FMAP 2 PLAN 20 TEMP -93.00 WGHT 0.051200 2.761200 WGHT 0.0512 2.7655 FVAR 0.10482 MOLE 1 N1 3 1.022778 0.755366 0.165011 11.00000 0.02847 0.04876 = 0.04945 0.00969 0.01136 -0.00348 N2 3 1.038054 0.471841 0.251169 11.00000 0.03134 0.02388 = 0.03673 0.00012 0.00777 0.00618 N3 3 0.733380 0.837242 0.254420 11.00000 0.03913 0.02501 = 0.04593 -0.00278 0.01319 -0.00170 N4 3 0.318280 0.681748 0.139016 11.00000 0.02353 0.04787 = 0.04533 0.00692 0.01250 -0.00019 C1 1 0.937733 0.746040 0.189776 11.00000 0.02962 0.02591 = 0.03015 0.00187 0.00531 -0.00204 C2 1 0.829188 0.737672 0.212860 11.00000 0.02134 0.02365 = 0.02994 -0.00025 0.00529 -0.00072 C3 1 0.780022 0.682196 0.210970 11.00000 0.02453 0.02500 = 0.02234 -0.00041 0.00433 0.00029 C4 1 0.845001 0.627155 0.230610 11.00000 0.02321 0.02305 = 0.02719 0.00152 0.00719 -0.00039 C5 1 0.954558 0.624458 0.337787 11.00000 0.02544 0.02266 = 0.02791 -0.00034 0.00738 -0.00156 AFIX 43 H5 2 0.986437 0.658912 0.404934 11.00000 -1.20000 AFIX 0 C6 1 1.017284 0.573358 0.348577 11.00000 0.02324 0.02649 = 0.02739 0.00121 0.00598 0.00166 AFIX 43 H6 2 1.090915 0.573117 0.424313 11.00000 -1.20000 AFIX 0 C7 1 0.974483 0.521314 0.249462 11.00000 0.02840 0.02525 = 0.02564 0.00399 0.01053 0.00351 C8 1 0.862617 0.523286 0.147116 11.00000 0.03105 0.02336 = 0.03000 -0.00295 0.00804 -0.00171 AFIX 43 H8 2 0.829621 0.488557 0.082866 11.00000 -1.20000 AFIX 0 C9 1 0.800661 0.574591 0.138867 11.00000 0.02356 0.02806 = 0.02921 0.00040 0.00547 -0.00024 AFIX 43 H9 2 0.725655 0.574387 0.068968 11.00000 -1.20000 AFIX 0 C10 1 1.154578 0.471905 0.349369 11.00000 0.03380 0.03090 = 0.04275 0.00476 0.01105 0.01037 AFIX 137 H10A 2 1.190467 0.507305 0.314342 11.00000 -1.50000 H10B 2 1.189849 0.435587 0.318788 11.00000 -1.50000 H10C 2 1.161933 0.472865 0.481143 11.00000 -1.50000 AFIX 0 C11 1 0.990093 0.416160 0.166964 11.00000 0.04400 0.02500 = 0.04589 -0.00226 0.01205 0.00465 AFIX 137 H11A 2 0.961278 0.422032 0.034920 11.00000 -1.50000 H11B 2 0.929725 0.404026 0.218926 11.00000 -1.50000 H11C 2 1.046918 0.384855 0.190233 11.00000 -1.50000 AFIX 0 C12 1 0.774018 0.792583 0.233717 11.00000 0.02581 0.02538 = 0.02882 0.00003 0.00578 -0.00534 C13 1 0.660136 0.679508 0.187718 11.00000 0.02266 0.02119 = 0.02741 -0.00338 0.00621 -0.00217 C14 1 0.612471 0.639552 0.286440 11.00000 0.02765 0.02217 = 0.02804 0.00025 0.00591 0.00020 AFIX 43 H14 2 0.658263 0.611573 0.366283 11.00000 -1.20000 AFIX 0 C15 1 0.500426 0.639827 0.270550 11.00000 0.02957 0.02772 = 0.03151 0.00241 0.01122 -0.00568 AFIX 43 H15 2 0.470846 0.612509 0.341256 11.00000 -1.20000 AFIX 0 C16 1 0.428921 0.679725 0.151791 11.00000 0.02154 0.03145 = 0.03211 -0.00290 0.00876 -0.00218 C17 1 0.476498 0.718277 0.047374 11.00000 0.02327 0.02784 = 0.03382 0.00397 0.00584 0.00350 AFIX 43 H17 2 0.430498 0.744947 -0.037147 11.00000 -1.20000 AFIX 0 C18 1 0.588653 0.718063 0.065456 11.00000 0.02659 0.02256 = 0.03202 0.00177 0.01093 -0.00119 AFIX 43 H18 2 0.618358 0.744748 -0.006833 11.00000 -1.20000 AFIX 0 C19 1 0.266687 0.636296 0.224413 11.00000 0.03120 0.06887 = 0.06325 0.00818 0.01850 -0.01291 AFIX 137 H19A 2 0.272218 0.597343 0.167794 11.00000 -1.50000 H19B 2 0.188656 0.646403 0.208224 11.00000 -1.50000 H19C 2 0.304205 0.634326 0.355120 11.00000 -1.50000 AFIX 0 C20 1 0.245579 0.718728 0.000031 11.00000 0.02527 0.08296 = 0.06522 0.02053 0.01361 0.01202 AFIX 137 H20A 2 0.169447 0.714839 0.009355 11.00000 -1.50000 H20B 2 0.249489 0.705541 -0.121266 11.00000 -1.50000 H20C 2 0.268819 0.760719 0.018363 11.00000 -1.50000 AFIX 0 MOLE 2 C21 1 0.491934 0.912751 0.299682 11.00000 0.06437 0.07227 = 0.06637 0.02309 0.01189 0.01329 AFIX 23 H21A 2 0.517643 0.906820 0.433532 11.00000 -1.20000 H21B 2 0.519417 0.878673 0.240555 11.00000 -1.20000 AFIX 0 CL1 4 0.347644 0.912191 0.233899 11.00000 0.06044 0.16602 = 0.08186 0.01366 -0.00201 0.02006 CL2 4 0.547562 0.977576 0.243957 11.00000 0.12111 0.09629 = 0.20732 0.09354 0.01872 -0.00137 HKLF 4 REM eca10lt in P2(1)/c REM R1 = 0.0541 for 2360 Fo > 4sig(Fo) and 0.0704 for all 2993 data REM 248 parameters refined using 0 restraints END WGHT 0.0512 2.7655 REM Highest difference peak 0.487, deepest hole -0.747, 1-sigma level 0.049 Q1 1 0.5574 0.9684 0.2090 11.00000 0.05 0.49 Q2 1 0.4604 0.9779 0.1788 11.00000 0.05 0.42 Q3 1 0.4738 0.9935 0.2867 11.00000 0.05 0.39 Q4 1 0.3942 0.8846 0.1893 11.00000 0.05 0.17 Q5 1 0.3386 0.9437 0.1496 11.00000 0.05 0.16 Q6 1 0.3682 0.9497 0.3119 11.00000 0.05 0.16 Q7 1 0.7220 0.6823 0.1904 11.00000 0.05 0.16 Q8 1 0.2862 0.8956 0.2233 11.00000 0.05 0.15 Q9 1 1.1933 0.4526 0.2283 11.00000 0.05 0.15 Q10 1 0.8141 0.6541 0.1934 11.00000 0.05 0.14 Q11 1 0.6213 0.6828 0.0881 11.00000 0.05 0.14 Q12 1 0.9844 0.3845 0.2599 11.00000 0.05 0.14 Q13 1 0.4413 1.0345 0.2979 11.00000 0.05 0.14 Q14 1 0.4575 0.9864 0.4030 11.00000 0.05 0.14 Q15 1 0.9021 0.4063 0.0782 11.00000 0.05 0.13 Q16 1 0.8152 0.6012 0.2266 11.00000 0.05 0.13 Q17 1 1.0850 0.7609 0.2836 11.00000 0.05 0.13 Q18 1 0.6399 0.6558 0.1973 11.00000 0.05 0.13 Q19 1 0.3802 0.9913 0.1253 11.00000 0.05 0.13 Q20 1 0.8190 0.5380 0.2439 11.00000 0.05 0.13 ; _cod_data_source_file J-Mater-Chem-C-2016-4-2979.cif _cod_data_source_block D _cod_original_sg_symbol_H-M P21/c _cod_database_code 7234646 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_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 N1 N 1.0228(2) 0.75537(12) 0.1650(4) 0.0420(7) Uani 1 1 d . . . N2 N 1.03805(19) 0.47184(10) 0.2512(3) 0.0309(6) Uani 1 1 d . . . N3 N 0.7334(2) 0.83724(11) 0.2544(3) 0.0363(6) Uani 1 1 d . . . N4 N 0.31828(19) 0.68175(12) 0.1390(4) 0.0383(6) Uani 1 1 d . . . C1 C 0.9377(2) 0.74604(12) 0.1898(4) 0.0291(7) Uani 1 1 d . . . C2 C 0.8292(2) 0.73767(12) 0.2129(4) 0.0253(6) Uani 1 1 d . . . C3 C 0.7800(2) 0.68220(12) 0.2110(3) 0.0243(6) Uani 1 1 d . . . C4 C 0.8450(2) 0.62716(12) 0.2306(4) 0.0244(6) Uani 1 1 d . . . C5 C 0.9546(2) 0.62446(12) 0.3378(4) 0.0253(6) Uani 1 1 d . . . H5 H 0.9864 0.6589 0.4049 0.030 Uiso 1 1 calc R . . C6 C 1.0173(2) 0.57336(12) 0.3486(4) 0.0258(6) Uani 1 1 d . . . H6 H 1.0909 0.5731 0.4243 0.031 Uiso 1 1 calc R . . C7 C 0.9745(2) 0.52131(12) 0.2495(4) 0.0258(6) Uani 1 1 d . . . C8 C 0.8626(2) 0.52329(12) 0.1471(4) 0.0281(6) Uani 1 1 d . . . H8 H 0.8296 0.4886 0.0829 0.034 Uiso 1 1 calc R . . C9 C 0.8007(2) 0.57459(12) 0.1389(4) 0.0272(6) Uani 1 1 d . . . H9 H 0.7257 0.5744 0.0690 0.033 Uiso 1 1 calc R . . C10 C 1.1546(2) 0.47190(13) 0.3494(4) 0.0356(7) Uani 1 1 d . . . H10A H 1.1905 0.5073 0.3143 0.053 Uiso 1 1 calc R . . H10B H 1.1898 0.4356 0.3188 0.053 Uiso 1 1 calc R . . H10C H 1.1619 0.4729 0.4811 0.053 Uiso 1 1 calc R . . C11 C 0.9901(3) 0.41616(13) 0.1670(4) 0.0383(8) Uani 1 1 d . . . H11A H 0.9613 0.4220 0.0349 0.057 Uiso 1 1 calc R . . H11B H 0.9297 0.4040 0.2189 0.057 Uiso 1 1 calc R . . H11C H 1.0469 0.3849 0.1902 0.057 Uiso 1 1 calc R . . C12 C 0.7740(2) 0.79258(13) 0.2337(4) 0.0269(6) Uani 1 1 d . . . C13 C 0.6601(2) 0.67951(11) 0.1877(4) 0.0238(6) Uani 1 1 d . . . C14 C 0.6125(2) 0.63955(12) 0.2864(4) 0.0262(6) Uani 1 1 d . . . H14 H 0.6583 0.6116 0.3663 0.031 Uiso 1 1 calc R . . C15 C 0.5004(2) 0.63983(12) 0.2706(4) 0.0290(7) Uani 1 1 d . . . H15 H 0.4708 0.6125 0.3413 0.035 Uiso 1 1 calc R . . C16 C 0.4289(2) 0.67972(12) 0.1518(4) 0.0281(6) Uani 1 1 d . . . C17 C 0.4765(2) 0.71828(12) 0.0474(4) 0.0286(6) Uani 1 1 d . . . H17 H 0.4305 0.7449 -0.0371 0.034 Uiso 1 1 calc R . . C18 C 0.5887(2) 0.71806(12) 0.0655(4) 0.0265(6) Uani 1 1 d . . . H18 H 0.6184 0.7447 -0.0068 0.032 Uiso 1 1 calc R . . C19 C 0.2667(3) 0.63630(17) 0.2244(5) 0.0533(10) Uani 1 1 d . . . H19A H 0.2722 0.5973 0.1678 0.080 Uiso 1 1 calc R . . H19B H 0.1887 0.6464 0.2082 0.080 Uiso 1 1 calc R . . H19C H 0.3042 0.6343 0.3551 0.080 Uiso 1 1 calc R . . C20 C 0.2456(3) 0.71873(19) 0.0000(5) 0.0575(10) Uani 1 1 d . . . H20A H 0.1694 0.7148 0.0094 0.086 Uiso 1 1 calc R . . H20B H 0.2495 0.7055 -0.1213 0.086 Uiso 1 1 calc R . . H20C H 0.2688 0.7607 0.0184 0.086 Uiso 1 1 calc R . . C21 C 0.4919(3) 0.9128(2) 0.2997(6) 0.0687(12) Uani 1 1 d . . . H21A H 0.5176 0.9068 0.4335 0.082 Uiso 1 1 calc R . . H21B H 0.5194 0.8787 0.2406 0.082 Uiso 1 1 calc R . . Cl1 Cl 0.34764(10) 0.91219(8) 0.23390(18) 0.1067(5) Uani 1 1 d . . . Cl2 Cl 0.54756(15) 0.97758(7) 0.2440(3) 0.1463(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 N1 0.0285(15) 0.0488(17) 0.0494(17) 0.0097(13) 0.0114(12) -0.0035(12) N2 0.0313(13) 0.0239(13) 0.0367(14) 0.0001(11) 0.0078(11) 0.0062(10) N3 0.0391(15) 0.0250(14) 0.0459(16) -0.0028(11) 0.0132(12) -0.0017(12) N4 0.0235(13) 0.0479(16) 0.0453(16) 0.0069(13) 0.0125(12) -0.0002(11) C1 0.0296(17) 0.0259(15) 0.0302(16) 0.0019(12) 0.0053(13) -0.0020(13) C2 0.0213(14) 0.0236(15) 0.0299(15) -0.0002(11) 0.0053(12) -0.0007(11) C3 0.0245(14) 0.0250(14) 0.0223(14) -0.0004(11) 0.0043(11) 0.0003(12) C4 0.0232(14) 0.0230(14) 0.0272(15) 0.0015(12) 0.0072(12) -0.0004(11) C5 0.0254(15) 0.0227(14) 0.0279(15) -0.0003(12) 0.0074(12) -0.0016(12) C6 0.0232(14) 0.0265(15) 0.0274(15) 0.0012(12) 0.0060(12) 0.0017(12) C7 0.0284(16) 0.0252(15) 0.0256(14) 0.0040(12) 0.0105(12) 0.0035(12) C8 0.0311(16) 0.0234(15) 0.0300(15) -0.0029(12) 0.0080(13) -0.0017(12) C9 0.0236(14) 0.0281(15) 0.0292(15) 0.0004(12) 0.0055(12) -0.0002(12) C10 0.0338(17) 0.0309(16) 0.0428(18) 0.0048(14) 0.0111(14) 0.0104(13) C11 0.0440(19) 0.0250(16) 0.0459(19) -0.0023(14) 0.0120(15) 0.0046(14) C12 0.0258(15) 0.0254(16) 0.0288(15) 0.0000(12) 0.0058(12) -0.0053(13) C13 0.0227(14) 0.0212(14) 0.0274(14) -0.0034(12) 0.0062(12) -0.0022(11) C14 0.0276(15) 0.0222(14) 0.0280(15) 0.0002(11) 0.0059(12) 0.0002(12) C15 0.0296(16) 0.0277(15) 0.0315(16) 0.0024(12) 0.0112(13) -0.0057(12) C16 0.0215(15) 0.0314(15) 0.0321(16) -0.0029(13) 0.0088(12) -0.0022(12) C17 0.0233(15) 0.0278(15) 0.0338(16) 0.0040(13) 0.0058(12) 0.0035(12) C18 0.0266(15) 0.0226(14) 0.0320(15) 0.0018(12) 0.0109(12) -0.0012(12) C19 0.0312(18) 0.069(2) 0.063(2) 0.0082(19) 0.0185(17) -0.0129(17) C20 0.0253(17) 0.083(3) 0.065(2) 0.021(2) 0.0136(17) 0.0120(18) C21 0.064(3) 0.072(3) 0.066(3) 0.023(2) 0.012(2) 0.013(2) Cl1 0.0604(8) 0.1660(15) 0.0819(9) 0.0137(9) -0.0020(6) 0.0201(8) Cl2 0.1211(13) 0.0963(11) 0.207(2) 0.0935(13) 0.0187(13) -0.0014(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' 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' 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 C7 N2 C11 121.1(2) . . C7 N2 C10 120.8(2) . . C11 N2 C10 118.0(2) . . C16 N4 C19 120.8(3) . . C16 N4 C20 120.0(3) . . C19 N4 C20 117.0(3) . . N1 C1 C2 176.3(3) . . C3 C2 C1 123.5(2) . . C3 C2 C12 122.6(2) . . C1 C2 C12 113.8(2) . . C2 C3 C4 121.1(2) . . C2 C3 C13 118.6(2) . . C4 C3 C13 120.3(2) . . C5 C4 C9 116.9(2) . . C5 C4 C3 122.1(2) . . C9 C4 C3 121.0(2) . . C6 C5 C4 121.9(3) . . C5 C6 C7 121.3(2) . . N2 C7 C6 121.6(2) . . N2 C7 C8 121.7(2) . . C6 C7 C8 116.7(2) . . C9 C8 C7 121.2(3) . . C8 C9 C4 121.9(3) . . N3 C12 C2 177.6(3) . . C14 C13 C18 117.2(2) . . C14 C13 C3 122.1(2) . . C18 C13 C3 120.7(2) . . C15 C14 C13 121.4(3) . . C14 C15 C16 121.4(3) . . N4 C16 C17 121.0(3) . . N4 C16 C15 122.0(3) . . C17 C16 C15 117.0(2) . . C18 C17 C16 121.1(3) . . C17 C18 C13 121.7(3) . . Cl2 C21 Cl1 113.3(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.150(4) . N2 C7 1.360(3) . N2 C11 1.453(4) . N2 C10 1.454(4) . N3 C12 1.149(4) . N4 C16 1.366(4) . N4 C19 1.445(4) . N4 C20 1.455(4) . C1 C2 1.430(4) . C2 C3 1.381(4) . C2 C12 1.436(4) . C3 C4 1.459(4) . C3 C13 1.468(4) . C4 C5 1.401(4) . C4 C9 1.402(4) . C5 C6 1.375(4) . C6 C7 1.410(4) . C7 C8 1.413(4) . C8 C9 1.376(4) . C13 C14 1.397(4) . C13 C18 1.402(4) . C14 C15 1.379(4) . C15 C16 1.408(4) . C16 C17 1.405(4) . C17 C18 1.377(4) . C21 Cl2 1.707(4) . C21 Cl1 1.746(4) .