#------------------------------------------------------------------------------ #$Date: 2018-05-16 17:28:01 +0300 (Wed, 16 May 2018) $ #$Revision: 207818 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/62/7156264.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_7156264 loop_ _publ_author_name 'Jia, Feng-Cheng' 'Xu, Cheng' 'Wang, Yu-Wei' 'Chen, Zhi-Peng' 'Chen, Yunfeng' 'Wu, An-Xin' _publ_section_title ; Copper-catalyzed ambient-temperature decarboxylative aunulation of isatins with amidine hydrochlorides: a facile access to 2-(1,3,5-triazin-2-yl)aniline derivatives ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C8OB00904J _journal_year 2018 _chemical_formula_sum 'C15 H15 Cl N4' _chemical_formula_weight 286.76 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-04-02 deposited with the CCDC. 2018-05-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.741(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.585(2) _cell_length_b 8.8309(18) _cell_length_c 15.039(3) _cell_measurement_reflns_used 3495 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 31.34 _cell_measurement_theta_min 2.50 _cell_volume 1396.1(5) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.882 _diffrn_measurement_device_type CCD _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_unetI/netI 0.0335 _diffrn_reflns_Laue_measured_fraction_full 0.975 _diffrn_reflns_Laue_measured_fraction_max 0.882 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 10228 _diffrn_reflns_point_group_measured_fraction_full 0.975 _diffrn_reflns_point_group_measured_fraction_max 0.882 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.150 _diffrn_reflns_theta_min 2.234 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.180 _exptl_transmission_factor_max 0.864 _exptl_transmission_factor_min 0.864 _refine_diff_density_max 1.084 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 4318 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0582 _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^)+(0.1173P)^2^+0.4488P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1829 _refine_ls_wR_factor_ref 0.2028 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3138 _reflns_number_total 4318 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ob00904j2.cif _cod_data_source_block 1_a _cod_database_code 7156264 _shelx_shelxl_version_number 2014/7 _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 0.943 _shelx_estimated_absorpt_t_max 0.953 _shelx_res_file ; 1_a.res created by SHELXL-2014/7 TITL 1_a.res in P2(1)/n CELL 0.71073 10.5855 8.8309 15.0391 90.000 96.741 90.000 ZERR 4.000 0.0022 0.0018 0.0031 0.000 0.003 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N Cl UNIT 60 60 16 4 L.S. 20 ACTA size 0.22 0.2 0.18 conf BOND $H FMAP 2 omit 2 3 4 omit -4 2 4 omit 1 3 0 PLAN 20 LIST 6 TEMP 0.000 WGHT 0.117300 0.448800 FVAR 0.53308 C1 1 0.177031 0.257062 0.421409 11.00000 0.07413 0.04780 = 0.08136 -0.01026 -0.00905 -0.00815 AFIX 23 H1A 2 0.162392 0.187529 0.371329 11.00000 -1.20000 H1B 2 0.234484 0.219975 0.471686 11.00000 -1.20000 AFIX 0 C2 1 0.070977 0.352775 0.440876 11.00000 0.05137 0.07081 = 0.07506 -0.00360 -0.00377 -0.01656 AFIX 23 H2A 2 0.062946 0.374504 0.503187 11.00000 -1.20000 H2B 2 -0.009122 0.342069 0.402862 11.00000 -1.20000 AFIX 0 C3 1 0.179696 0.423560 0.400903 11.00000 0.06062 0.05109 = 0.04379 -0.00150 -0.00568 -0.01058 AFIX 13 H3 2 0.162499 0.450087 0.337360 11.00000 -1.20000 AFIX 0 C4 1 0.272174 0.520712 0.454125 11.00000 0.04289 0.03980 = 0.03921 -0.00029 0.00079 0.00179 C5 1 0.419871 0.704424 0.459495 11.00000 0.03733 0.03672 = 0.03904 0.00372 0.00601 0.00480 C6 1 0.383593 0.584828 0.587155 11.00000 0.03519 0.03344 = 0.03502 0.00113 0.00434 0.00417 C7 1 0.488497 0.821938 0.415843 11.00000 0.04759 0.04892 = 0.04511 0.01057 0.00320 -0.00499 AFIX 13 H7 2 0.562458 0.865454 0.452294 11.00000 -1.20000 AFIX 0 C8 1 0.496807 0.815694 0.317381 11.00000 0.07194 0.06014 = 0.04913 0.01427 0.01608 -0.00019 AFIX 23 H8A 2 0.574998 0.850329 0.296287 11.00000 -1.20000 H8B 2 0.456080 0.731241 0.284177 11.00000 -1.20000 AFIX 0 C9 1 0.415380 0.928642 0.351514 11.00000 0.06534 0.04720 = 0.07278 0.02309 0.00669 0.00444 AFIX 23 H9A 2 0.324119 0.914249 0.339583 11.00000 -1.20000 H9B 2 0.443061 1.033363 0.351695 11.00000 -1.20000 AFIX 0 C10 1 0.410148 0.575938 0.685563 11.00000 0.03725 0.03272 = 0.03391 0.00136 0.00272 0.00176 C11 1 0.331182 0.496135 0.739940 11.00000 0.03857 0.03335 = 0.04141 0.00002 0.00565 -0.00044 C12 1 0.364156 0.505874 0.833372 11.00000 0.04509 0.03805 = 0.04054 0.00270 0.00644 0.00154 C13 1 0.467002 0.586214 0.871744 11.00000 0.05211 0.04499 = 0.03914 0.00277 -0.00064 0.00232 AFIX 43 H13 2 0.484617 0.590125 0.933756 11.00000 -1.20000 AFIX 0 C14 1 0.544728 0.661500 0.818741 11.00000 0.04503 0.05030 = 0.04679 0.00192 -0.00581 -0.00745 AFIX 43 H14 2 0.614981 0.715499 0.844724 11.00000 -1.20000 AFIX 0 C15 1 0.516955 0.655710 0.726637 11.00000 0.03913 0.03956 = 0.04282 0.00312 -0.00040 -0.00326 AFIX 43 H15 2 0.569831 0.705488 0.690961 11.00000 -1.20000 AFIX 0 CL1 4 0.268724 0.411861 0.901870 11.00000 0.07074 0.06533 = 0.04884 0.00912 0.01874 -0.01128 N1 3 0.329037 0.626164 0.409716 11.00000 0.04719 0.03975 = 0.03677 0.00394 0.00013 0.00075 N2 3 0.452489 0.686575 0.547254 11.00000 0.03807 0.04052 = 0.03668 0.00233 0.00389 -0.00090 N3 3 0.293998 0.496608 0.542925 11.00000 0.04304 0.03727 = 0.03669 0.00044 0.00286 -0.00227 N4 3 0.227511 0.418145 0.705508 11.00000 0.05333 0.06644 = 0.04417 0.00008 0.00951 -0.02230 AFIX 93 H4A 2 0.180689 0.373673 0.740588 11.00000 -1.20000 H4B 2 0.208125 0.412810 0.648440 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P2(1)/n REM R1 = 0.0582 for 3138 Fo > 4sig(Fo) and 0.0784 for all 4318 data REM 181 parameters refined using 0 restraints END WGHT 0.1066 0.4574 REM Highest difference peak 1.084, deepest hole -0.329, 1-sigma level 0.059 Q1 1 0.5645 0.6476 0.9115 11.00000 0.05 1.08 Q2 1 0.4555 0.5960 0.7341 11.00000 0.05 0.46 Q3 1 0.3590 0.5254 0.6931 11.00000 0.05 0.41 Q4 1 0.4249 0.5519 0.8379 11.00000 0.05 0.39 Q5 1 0.4084 0.6365 0.5582 11.00000 0.05 0.33 Q6 1 0.2833 0.5173 0.5031 11.00000 0.05 0.31 Q7 1 0.2477 0.4145 0.8043 11.00000 0.05 0.30 Q8 1 0.3247 0.5637 0.5677 11.00000 0.05 0.29 Q9 1 0.3874 0.5807 0.6353 11.00000 0.05 0.28 Q10 1 0.3143 0.5798 0.4280 11.00000 0.05 0.26 Q11 1 0.4422 0.6866 0.5098 11.00000 0.05 0.26 Q12 1 0.2277 0.4801 0.4306 11.00000 0.05 0.25 Q13 1 0.2802 0.4660 0.7150 11.00000 0.05 0.24 Q14 1 0.3439 0.4978 0.7902 11.00000 0.05 0.24 Q15 1 0.5217 0.6550 0.7677 11.00000 0.05 0.24 Q16 1 0.1807 0.4240 0.3746 11.00000 0.05 0.24 Q17 1 0.1173 0.2993 0.4426 11.00000 0.05 0.22 Q18 1 0.3781 0.6459 0.4388 11.00000 0.05 0.21 Q19 1 0.1250 0.4262 0.4258 11.00000 0.05 0.21 Q20 1 0.4159 0.9176 0.3785 11.00000 0.05 0.21 ; _shelx_res_checksum 1183 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C1 C 0.1770(3) 0.2571(3) 0.4214(2) 0.0692(7) Uani 1 1 d . . H1A H 0.1624 0.1875 0.3713 0.083 Uiso 1 1 calc R U H1B H 0.2345 0.2200 0.4717 0.083 Uiso 1 1 calc R U C2 C 0.0710(2) 0.3528(3) 0.44088(19) 0.0666(7) Uani 1 1 d . . H2A H 0.0629 0.3745 0.5032 0.080 Uiso 1 1 calc R U H2B H -0.0091 0.3421 0.4029 0.080 Uiso 1 1 calc R U C3 C 0.1797(2) 0.4236(3) 0.40090(14) 0.0528(5) Uani 1 1 d . . H3 H 0.1625 0.4501 0.3374 0.063 Uiso 1 1 calc R U C4 C 0.27217(18) 0.5207(2) 0.45413(12) 0.0410(4) Uani 1 1 d . . C5 C 0.41987(16) 0.7044(2) 0.45949(11) 0.0376(4) Uani 1 1 d . . C6 C 0.38359(16) 0.58483(19) 0.58715(11) 0.0345(3) Uani 1 1 d . . C7 C 0.4885(2) 0.8219(2) 0.41584(13) 0.0474(4) Uani 1 1 d . . H7 H 0.5625 0.8655 0.4523 0.057 Uiso 1 1 calc R U C8 C 0.4968(3) 0.8157(3) 0.31738(15) 0.0597(6) Uani 1 1 d . . H8A H 0.5750 0.8503 0.2963 0.072 Uiso 1 1 calc R U H8B H 0.4561 0.7312 0.2842 0.072 Uiso 1 1 calc R U C9 C 0.4154(3) 0.9286(3) 0.35151(18) 0.0619(6) Uani 1 1 d . . H9A H 0.3241 0.9142 0.3396 0.074 Uiso 1 1 calc R U H9B H 0.4431 1.0334 0.3517 0.074 Uiso 1 1 calc R U C10 C 0.41015(16) 0.57594(19) 0.68556(11) 0.0347(3) Uani 1 1 d . . C11 C 0.33118(17) 0.4961(2) 0.73994(12) 0.0377(4) Uani 1 1 d . . C12 C 0.36416(18) 0.5059(2) 0.83337(12) 0.0411(4) Uani 1 1 d . . C13 C 0.4670(2) 0.5862(2) 0.87174(13) 0.0459(4) Uani 1 1 d . . H13 H 0.4846 0.5901 0.9338 0.055 Uiso 1 1 calc R U C14 C 0.5447(2) 0.6615(3) 0.81874(13) 0.0483(5) Uani 1 1 d . . H14 H 0.6150 0.7155 0.8447 0.058 Uiso 1 1 calc R U C15 C 0.51695(17) 0.6557(2) 0.72664(12) 0.0409(4) Uani 1 1 d . . H15 H 0.5698 0.7055 0.6910 0.049 Uiso 1 1 calc R U Cl1 Cl 0.26872(6) 0.41186(7) 0.90187(4) 0.0607(2) Uani 1 1 d . . N1 N 0.32904(16) 0.62616(19) 0.40972(10) 0.0416(3) Uani 1 1 d . . N2 N 0.45249(14) 0.68658(18) 0.54725(9) 0.0385(3) Uani 1 1 d . . N3 N 0.29400(15) 0.49661(18) 0.54292(10) 0.0391(3) Uani 1 1 d . . N4 N 0.22751(18) 0.4181(2) 0.70551(12) 0.0543(5) Uani 1 1 d . . H4A H 0.1807 0.3737 0.7406 0.065 Uiso 1 1 calc R U H4B H 0.2081 0.4128 0.6484 0.065 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 C1 0.0741(16) 0.0478(14) 0.0814(16) -0.0103(12) -0.0091(13) -0.0081(12) C2 0.0514(12) 0.0708(17) 0.0751(15) -0.0036(13) -0.0038(11) -0.0166(12) C3 0.0606(12) 0.0511(13) 0.0438(10) -0.0015(8) -0.0057(9) -0.0106(9) C4 0.0429(9) 0.0398(10) 0.0392(8) -0.0003(7) 0.0008(6) 0.0018(7) C5 0.0373(8) 0.0367(9) 0.0390(8) 0.0037(6) 0.0060(6) 0.0048(6) C6 0.0352(8) 0.0334(9) 0.0350(7) 0.0011(6) 0.0043(6) 0.0042(6) C7 0.0476(10) 0.0489(12) 0.0451(9) 0.0106(8) 0.0032(7) -0.0050(8) C8 0.0719(15) 0.0601(14) 0.0491(11) 0.0143(10) 0.0161(10) -0.0002(11) C9 0.0653(14) 0.0472(13) 0.0728(15) 0.0231(11) 0.0067(11) 0.0044(10) C10 0.0372(8) 0.0327(9) 0.0339(7) 0.0014(6) 0.0027(6) 0.0018(6) C11 0.0386(8) 0.0334(9) 0.0414(8) 0.0000(6) 0.0057(6) -0.0004(6) C12 0.0451(9) 0.0380(10) 0.0405(8) 0.0027(7) 0.0064(7) 0.0015(7) C13 0.0521(11) 0.0450(11) 0.0391(8) 0.0028(7) -0.0006(7) 0.0023(8) C14 0.0450(10) 0.0503(12) 0.0468(9) 0.0019(8) -0.0058(7) -0.0074(8) C15 0.0391(8) 0.0396(10) 0.0428(8) 0.0031(7) -0.0004(7) -0.0033(7) Cl1 0.0707(4) 0.0653(4) 0.0488(3) 0.0091(2) 0.0187(2) -0.0113(3) N1 0.0472(8) 0.0397(9) 0.0368(7) 0.0039(6) 0.0001(6) 0.0008(6) N2 0.0381(7) 0.0405(9) 0.0367(7) 0.0023(6) 0.0039(5) -0.0009(6) N3 0.0430(8) 0.0373(9) 0.0367(7) 0.0004(6) 0.0029(6) -0.0023(6) N4 0.0533(10) 0.0664(12) 0.0442(8) 0.0001(8) 0.0095(7) -0.0223(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 C2 C1 C3 60.59(18) C2 C1 H1A 117.7 C3 C1 H1A 117.7 C2 C1 H1B 117.7 C3 C1 H1B 117.7 H1A C1 H1B 114.8 C1 C2 C3 61.07(18) C1 C2 H2A 117.7 C3 C2 H2A 117.7 C1 C2 H2B 117.7 C3 C2 H2B 117.7 H2A C2 H2B 114.8 C4 C3 C2 121.4(2) C4 C3 C1 119.2(2) C2 C3 C1 58.34(18) C4 C3 H3 115.3 C2 C3 H3 115.3 C1 C3 H3 115.3 N1 C4 N3 125.03(17) N1 C4 C3 116.60(17) N3 C4 C3 118.36(18) N1 C5 N2 125.28(16) N1 C5 C7 118.43(16) N2 C5 C7 116.27(17) N2 C6 N3 123.81(15) N2 C6 C10 115.75(15) N3 C6 C10 120.44(15) C5 C7 C8 120.50(19) C5 C7 C9 119.26(18) C8 C7 C9 57.98(16) C5 C7 H7 115.6 C8 C7 H7 115.6 C9 C7 H7 115.6 C9 C8 C7 61.16(16) C9 C8 H8A 117.7 C7 C8 H8A 117.7 C9 C8 H8B 117.7 C7 C8 H8B 117.7 H8A C8 H8B 114.8 C8 C9 C7 60.86(15) C8 C9 H9A 117.7 C7 C9 H9A 117.7 C8 C9 H9B 117.7 C7 C9 H9B 117.7 H9A C9 H9B 114.8 C15 C10 C11 119.35(15) C15 C10 C6 117.44(15) C11 C10 C6 123.17(16) N4 C11 C12 120.64(17) N4 C11 C10 122.65(16) C12 C11 C10 116.69(16) C13 C12 C11 122.90(17) C13 C12 Cl1 119.14(15) C11 C12 Cl1 117.96(14) C12 C13 C14 120.28(18) C12 C13 H13 119.9 C14 C13 H13 119.9 C13 C14 C15 119.29(18) C13 C14 H14 120.4 C15 C14 H14 120.4 C14 C15 C10 121.47(17) C14 C15 H15 119.3 C10 C15 H15 119.3 C4 N1 C5 114.71(15) C5 N2 C6 115.49(15) C4 N3 C6 115.42(16) C11 N4 H4A 120.0 C11 N4 H4B 120.0 H4A N4 H4B 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.462(4) C1 C3 1.503(4) C1 H1A 0.9700 C1 H1B 0.9700 C2 C3 1.496(3) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.467(3) C3 H3 0.9800 C4 N1 1.330(2) C4 N3 1.345(2) C5 N1 1.339(2) C5 N2 1.334(2) C5 C7 1.465(3) C6 N2 1.342(2) C6 N3 1.342(2) C6 C10 1.476(2) C7 C8 1.495(3) C7 C9 1.499(3) C7 H7 0.9800 C8 C9 1.451(4) C8 H8A 0.9700 C8 H8B 0.9700 C9 H9A 0.9700 C9 H9B 0.9700 C10 C15 1.411(2) C10 C11 1.423(2) C11 N4 1.347(2) C11 C12 1.410(2) C12 C13 1.369(3) C12 Cl1 1.7365(19) C13 C14 1.381(3) C13 H13 0.9300 C14 C15 1.383(3) C14 H14 0.9300 C15 H15 0.9300 N4 H4A 0.8600 N4 H4B 0.8600 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 C1 C2 C3 C4 -107.2(3) C2 C1 C3 C4 110.9(2) C2 C3 C4 N1 -152.3(2) C1 C3 C4 N1 139.1(2) C2 C3 C4 N3 28.3(3) C1 C3 C4 N3 -40.4(3) N1 C5 C7 C8 -23.9(3) N2 C5 C7 C8 157.31(19) N1 C5 C7 C9 44.0(3) N2 C5 C7 C9 -134.7(2) C5 C7 C8 C9 107.5(2) C5 C7 C9 C8 -109.6(2) N2 C6 C10 C15 -9.7(2) N3 C6 C10 C15 171.34(16) N2 C6 C10 C11 167.97(16) N3 C6 C10 C11 -11.0(3) C15 C10 C11 N4 179.72(18) C6 C10 C11 N4 2.1(3) C15 C10 C11 C12 1.6(3) C6 C10 C11 C12 -176.01(16) N4 C11 C12 C13 -178.6(2) C10 C11 C12 C13 -0.5(3) N4 C11 C12 Cl1 1.1(3) C10 C11 C12 Cl1 179.20(13) C11 C12 C13 C14 -0.6(3) Cl1 C12 C13 C14 179.74(16) C12 C13 C14 C15 0.5(3) C13 C14 C15 C10 0.7(3) C11 C10 C15 C14 -1.8(3) C6 C10 C15 C14 176.00(18) N3 C4 N1 C5 4.5(3) C3 C4 N1 C5 -174.98(18) N2 C5 N1 C4 -2.0(3) C7 C5 N1 C4 179.39(17) N1 C5 N2 C6 -2.5(3) C7 C5 N2 C6 176.19(16) N3 C6 N2 C5 5.0(3) C10 C6 N2 C5 -173.88(15) N1 C4 N3 C6 -2.2(3) C3 C4 N3 C6 177.20(17) N2 C6 N3 C4 -2.9(3) C10 C6 N3 C4 176.01(16)