#------------------------------------------------------------------------------ #$Date: 2021-06-05 22:29:16 +0300 (Sat, 05 Jun 2021) $ #$Revision: 266172 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158013.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_7158013 loop_ _publ_author_name 'Jin, Jiang' 'Li, Yinghua' 'Xiang, Shiqun' 'Fan, Weibin' 'Guo, Shiwei' 'Huang, Deguang' _publ_section_title ; Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4076 _journal_page_last 4081 _journal_paper_doi 10.1039/d1ob00120e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C21 H20 Cl2 N2' _chemical_formula_sum 'C21 H20 Cl2 N2' _chemical_formula_weight 371.29 _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 geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-01-15 deposited with the CCDC. 2021-04-06 downloaded from the CCDC. ; _cell_angle_alpha 110.640(5) _cell_angle_beta 90.771(4) _cell_angle_gamma 112.601(5) _cell_formula_units_Z 2 _cell_length_a 8.8647(5) _cell_length_b 10.0294(6) _cell_length_c 11.7597(5) _cell_measurement_reflns_used 2922 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 72.2960 _cell_measurement_theta_min 4.0470 _cell_volume 889.76(10) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10.5594 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6815 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.924 _diffrn_reflns_theta_min 4.078 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 3.310 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75052 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.386 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 388 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.620 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 226 _refine_ls_number_reflns 3346 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0486 _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^)+(0.0859P)^2^+0.7289P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1441 _refine_ls_wR_factor_ref 0.1501 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2884 _reflns_number_total 3346 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00120e2.cif _cod_data_source_block Compound3m _cod_depositor_comments 'Adding full bibliography for 7158011--7158015.cif.' _cod_original_cell_volume 889.76(9) _cod_database_code 7158013 _shelx_shelxl_version_number 2018/3 _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 0.557 _shelx_estimated_absorpt_t_max 0.733 _shelx_res_file ; TITL full.res in P-1 full.res created by SHELXL-2018/3 at 22:29:33 on 18-Nov-2020 CELL 1.54184 8.8647 10.0294 11.7597 110.64 90.771 112.601 ZERR 2 0.0005 0.0006 0.0005 0.005 0.004 0.005 LATT 1 SFAC C H Cl N UNIT 42 40 4 4 TEMP -123 SIZE 0.15 0.10 0.20 OMIT 0 140 L.S. 4 PLAN 1 fmap 2 MORE -1 BOND $H ACTA CONF WGHT 0.085900 0.728900 FVAR 0.87264 CL1 3 0.472773 1.030586 0.661478 11.00000 0.03747 0.03014 = 0.02875 0.00368 0.00400 0.01108 CL2 3 0.277133 0.012635 -0.053405 11.00000 0.04582 0.02936 = 0.03285 0.01028 0.00931 0.02069 N1 4 0.266601 0.360296 0.532624 11.00000 0.03208 0.03487 = 0.02943 0.01597 0.01107 0.01720 N2 4 0.205057 0.601828 0.088614 11.00000 0.02855 0.02459 = 0.02738 0.01033 0.00314 0.01014 C1 1 0.144131 0.300919 0.430057 11.00000 0.03000 0.03097 = 0.02731 0.01167 0.01186 0.01362 C2 1 0.135973 0.421920 0.405711 11.00000 0.02494 0.02989 = 0.02227 0.00945 0.01017 0.01183 C3 1 0.255777 0.564036 0.498114 11.00000 0.02322 0.03396 = 0.02035 0.01040 0.00950 0.01414 C4 1 0.298400 0.722535 0.525223 11.00000 0.02234 0.03299 = 0.02225 0.01017 0.00653 0.01163 AFIX 43 H4A 2 0.247421 0.754584 0.474525 11.00000 -1.20000 AFIX 0 C5 1 0.416504 0.831071 0.627605 11.00000 0.02542 0.03138 = 0.02426 0.00731 0.00862 0.01197 C6 1 0.495186 0.788980 0.704721 11.00000 0.02744 0.04250 = 0.02287 0.00772 0.00269 0.01273 AFIX 43 H6A 2 0.575757 0.867808 0.774590 11.00000 -1.20000 AFIX 0 C7 1 0.455478 0.632922 0.679033 11.00000 0.02854 0.04760 = 0.02438 0.01531 0.00541 0.01816 AFIX 43 H7A 2 0.508312 0.602619 0.730078 11.00000 -1.20000 AFIX 0 C8 1 0.335334 0.520644 0.575802 11.00000 0.02691 0.03630 = 0.02539 0.01339 0.01160 0.01674 C9 1 0.317820 0.268615 0.583511 11.00000 0.04063 0.04674 = 0.03852 0.02373 0.01511 0.02714 AFIX 33 H9A 2 0.249740 0.156839 0.536575 11.00000 -1.50000 H9B 2 0.434747 0.291308 0.578232 11.00000 -1.50000 H9C 2 0.303517 0.295861 0.670047 11.00000 -1.50000 AFIX 0 C10 1 0.046037 0.128344 0.365254 11.00000 0.04560 0.03020 = 0.03901 0.01260 0.01141 0.01341 AFIX 33 H10A 2 0.082853 0.073657 0.406305 11.00000 -1.50000 H10B 2 -0.071948 0.102841 0.367657 11.00000 -1.50000 H10C 2 0.062803 0.095231 0.279253 11.00000 -1.50000 AFIX 0 C11 1 0.020697 0.413735 0.305760 11.00000 0.02288 0.02981 = 0.02363 0.00635 0.00453 0.00960 AFIX 23 H11A 2 -0.063228 0.304315 0.264745 11.00000 -1.20000 H11B 2 -0.038640 0.479497 0.344421 11.00000 -1.20000 AFIX 0 C12 1 0.125412 0.598629 0.189139 11.00000 0.02046 0.02661 = 0.02472 0.00492 -0.00067 0.00956 C13 1 0.104505 0.466167 0.209266 11.00000 0.01954 0.02775 = 0.02123 0.00517 0.00076 0.00885 C14 1 0.172726 0.381384 0.115997 11.00000 0.01956 0.02493 = 0.02039 0.00671 0.00055 0.00811 C15 1 0.184927 0.237564 0.086026 11.00000 0.02467 0.02527 = 0.02264 0.00969 0.00322 0.00838 AFIX 43 H15A 2 0.144744 0.175738 0.133490 11.00000 -1.20000 AFIX 0 C16 1 0.257180 0.189543 -0.014553 11.00000 0.02586 0.02505 = 0.02426 0.00568 0.00143 0.01149 C17 1 0.317193 0.276239 -0.087767 11.00000 0.02793 0.03328 = 0.02191 0.00850 0.00580 0.01327 AFIX 43 H17A 2 0.365848 0.237921 -0.156353 11.00000 -1.20000 AFIX 0 C18 1 0.305629 0.417237 -0.060259 11.00000 0.02767 0.03028 = 0.02225 0.01280 0.00460 0.00968 AFIX 43 H18A 2 0.345240 0.477201 -0.109153 11.00000 -1.20000 AFIX 0 C19 1 0.233676 0.468951 0.041967 11.00000 0.02210 0.02594 = 0.02315 0.00940 0.00051 0.00877 C20 1 0.245911 0.720615 0.036209 11.00000 0.03825 0.02936 = 0.03220 0.01410 -0.00226 0.01389 AFIX 33 H20A 2 0.213640 0.803659 0.085738 11.00000 -1.50000 H20B 2 0.365573 0.765352 0.036287 11.00000 -1.50000 H20C 2 0.186003 0.672743 -0.048652 11.00000 -1.50000 AFIX 0 C21 1 0.073401 0.726658 0.257292 11.00000 0.03173 0.02869 = 0.03712 0.00515 -0.00097 0.01645 AFIX 33 H21A 2 0.106449 0.805030 0.220300 11.00000 -1.50000 H21B 2 -0.047330 0.682453 0.252193 11.00000 -1.50000 H21C 2 0.127050 0.776263 0.343977 11.00000 -1.50000 AFIX 0 HKLF 4 REM full.res in P-1 REM wR2 = 0.1501, GooF = S = 1.063, Restrained GooF = 1.063 for all data REM R1 = 0.0486 for 2884 Fo > 4sig(Fo) and 0.0567 for all 3346 data REM 226 parameters refined using 0 restraints END WGHT 0.0859 0.7286 REM Highest difference peak 0.620, deepest hole -0.530, 1-sigma level 0.069 Q1 1 0.0078 0.6957 0.3217 11.00000 0.05 0.62 ; _shelx_res_checksum 11563 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 0.47277(8) 1.03059(8) 0.66148(6) 0.0354(2) Uani 1 1 d . . . . . Cl2 Cl 0.27713(9) 0.01264(8) -0.05341(6) 0.0348(2) Uani 1 1 d . . . . . N1 N 0.2666(3) 0.3603(3) 0.5326(2) 0.0299(5) Uani 1 1 d . . . . . N2 N 0.2051(3) 0.6018(2) 0.0886(2) 0.0271(5) Uani 1 1 d . . . . . C1 C 0.1441(3) 0.3009(3) 0.4301(2) 0.0289(6) Uani 1 1 d . . . . . C2 C 0.1360(3) 0.4219(3) 0.4057(2) 0.0257(5) Uani 1 1 d . . . . . C3 C 0.2558(3) 0.5640(3) 0.4981(2) 0.0251(5) Uani 1 1 d . . . . . C4 C 0.2984(3) 0.7225(3) 0.5252(2) 0.0259(5) Uani 1 1 d . . . . . H4A H 0.247421 0.754584 0.474525 0.031 Uiso 1 1 calc R U . . . C5 C 0.4165(3) 0.8311(3) 0.6276(2) 0.0280(6) Uani 1 1 d . . . . . C6 C 0.4952(3) 0.7890(4) 0.7047(2) 0.0330(6) Uani 1 1 d . . . . . H6A H 0.575757 0.867808 0.774590 0.040 Uiso 1 1 calc R U . . . C7 C 0.4555(3) 0.6329(4) 0.6790(2) 0.0323(6) Uani 1 1 d . . . . . H7A H 0.508312 0.602619 0.730078 0.039 Uiso 1 1 calc R U . . . C8 C 0.3353(3) 0.5206(3) 0.5758(2) 0.0278(5) Uani 1 1 d . . . . . C9 C 0.3178(4) 0.2686(4) 0.5835(3) 0.0367(7) Uani 1 1 d . . . . . H9A H 0.249740 0.156839 0.536575 0.055 Uiso 1 1 calc R U . . . H9B H 0.434747 0.291308 0.578232 0.055 Uiso 1 1 calc R U . . . H9C H 0.303517 0.295861 0.670047 0.055 Uiso 1 1 calc R U . . . C10 C 0.0460(4) 0.1283(3) 0.3653(3) 0.0392(7) Uani 1 1 d . . . . . H10A H 0.082853 0.073657 0.406305 0.059 Uiso 1 1 calc R U . . . H10B H -0.071948 0.102841 0.367657 0.059 Uiso 1 1 calc R U . . . H10C H 0.062803 0.095231 0.279253 0.059 Uiso 1 1 calc R U . . . C11 C 0.0207(3) 0.4137(3) 0.3058(2) 0.0271(5) Uani 1 1 d . . . . . H11A H -0.063228 0.304315 0.264745 0.032 Uiso 1 1 calc R U . . . H11B H -0.038640 0.479497 0.344421 0.032 Uiso 1 1 calc R U . . . C12 C 0.1254(3) 0.5986(3) 0.1891(2) 0.0256(5) Uani 1 1 d . . . . . C13 C 0.1045(3) 0.4662(3) 0.2093(2) 0.0245(5) Uani 1 1 d . . . . . C14 C 0.1727(3) 0.3814(3) 0.1160(2) 0.0227(5) Uani 1 1 d . . . . . C15 C 0.1849(3) 0.2376(3) 0.0860(2) 0.0247(5) Uani 1 1 d . . . . . H15A H 0.144744 0.175738 0.133490 0.030 Uiso 1 1 calc R U . . . C16 C 0.2572(3) 0.1895(3) -0.0146(2) 0.0260(5) Uani 1 1 d . . . . . C17 C 0.3172(3) 0.2762(3) -0.0878(2) 0.0282(6) Uani 1 1 d . . . . . H17A H 0.365848 0.237921 -0.156353 0.034 Uiso 1 1 calc R U . . . C18 C 0.3056(3) 0.4172(3) -0.0603(2) 0.0267(5) Uani 1 1 d . . . . . H18A H 0.345240 0.477201 -0.109153 0.032 Uiso 1 1 calc R U . . . C19 C 0.2337(3) 0.4690(3) 0.0420(2) 0.0242(5) Uani 1 1 d . . . . . C20 C 0.2459(4) 0.7206(3) 0.0362(3) 0.0328(6) Uani 1 1 d . . . . . H20A H 0.213640 0.803659 0.085738 0.049 Uiso 1 1 calc R U . . . H20B H 0.365573 0.765352 0.036287 0.049 Uiso 1 1 calc R U . . . H20C H 0.186003 0.672743 -0.048652 0.049 Uiso 1 1 calc R U . . . C21 C 0.0734(3) 0.7267(3) 0.2573(3) 0.0336(6) Uani 1 1 d . . . . . H21A H 0.106449 0.805030 0.220300 0.050 Uiso 1 1 calc R U . . . H21B H -0.047330 0.682453 0.252193 0.050 Uiso 1 1 calc R U . . . H21C H 0.127050 0.776263 0.343977 0.050 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 0.0375(4) 0.0301(4) 0.0287(3) 0.0037(3) 0.0040(3) 0.0111(3) Cl2 0.0458(4) 0.0294(3) 0.0328(4) 0.0103(3) 0.0093(3) 0.0207(3) N1 0.0321(12) 0.0349(12) 0.0294(11) 0.0160(10) 0.0111(9) 0.0172(10) N2 0.0286(11) 0.0246(11) 0.0274(11) 0.0103(9) 0.0031(9) 0.0101(9) C1 0.0300(13) 0.0310(14) 0.0273(13) 0.0117(11) 0.0119(10) 0.0136(11) C2 0.0249(12) 0.0299(13) 0.0223(12) 0.0094(10) 0.0102(10) 0.0118(10) C3 0.0232(12) 0.0340(14) 0.0204(12) 0.0104(10) 0.0095(9) 0.0141(11) C4 0.0223(12) 0.0330(13) 0.0222(12) 0.0102(10) 0.0065(9) 0.0116(10) C5 0.0254(12) 0.0314(13) 0.0243(12) 0.0073(10) 0.0086(10) 0.0120(11) C6 0.0274(13) 0.0425(16) 0.0229(13) 0.0077(11) 0.0027(10) 0.0127(12) C7 0.0285(13) 0.0476(16) 0.0244(13) 0.0153(12) 0.0054(10) 0.0182(12) C8 0.0269(12) 0.0363(14) 0.0254(13) 0.0134(11) 0.0116(10) 0.0167(11) C9 0.0406(16) 0.0467(17) 0.0385(16) 0.0237(14) 0.0151(12) 0.0271(14) C10 0.0456(17) 0.0302(15) 0.0390(16) 0.0126(12) 0.0114(13) 0.0134(13) C11 0.0229(12) 0.0298(13) 0.0236(12) 0.0064(10) 0.0045(10) 0.0096(10) C12 0.0205(11) 0.0266(12) 0.0247(12) 0.0049(10) -0.0007(9) 0.0096(10) C13 0.0195(11) 0.0277(13) 0.0212(12) 0.0052(10) 0.0008(9) 0.0088(10) C14 0.0196(11) 0.0249(12) 0.0204(11) 0.0067(9) 0.0006(9) 0.0081(9) C15 0.0247(12) 0.0253(12) 0.0226(12) 0.0097(10) 0.0032(10) 0.0084(10) C16 0.0259(12) 0.0251(12) 0.0243(12) 0.0057(10) 0.0014(10) 0.0115(10) C17 0.0279(13) 0.0333(14) 0.0219(12) 0.0085(11) 0.0058(10) 0.0133(11) C18 0.0277(13) 0.0303(13) 0.0223(12) 0.0128(10) 0.0046(10) 0.0097(11) C19 0.0221(12) 0.0259(12) 0.0232(12) 0.0094(10) 0.0005(9) 0.0088(10) C20 0.0382(15) 0.0294(14) 0.0322(14) 0.0141(11) -0.0023(11) 0.0139(12) C21 0.0317(14) 0.0287(13) 0.0371(15) 0.0052(11) -0.0010(11) 0.0164(11) 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 C8 N1 C1 108.7(2) . . ? C8 N1 C9 125.1(2) . . ? C1 N1 C9 126.1(2) . . ? C19 N2 C12 108.4(2) . . ? C19 N2 C20 124.8(2) . . ? C12 N2 C20 126.7(2) . . ? C2 C1 N1 109.6(2) . . ? C2 C1 C10 130.1(3) . . ? N1 C1 C10 120.3(2) . . ? C1 C2 C3 106.9(2) . . ? C1 C2 C11 128.2(2) . . ? C3 C2 C11 124.8(2) . . ? C4 C3 C8 119.3(2) . . ? C4 C3 C2 133.6(2) . . ? C8 C3 C2 107.0(2) . . ? C5 C4 C3 118.1(2) . . ? C5 C4 H4A 121.0 . . ? C3 C4 H4A 121.0 . . ? C4 C5 C6 122.9(3) . . ? C4 C5 Cl1 118.4(2) . . ? C6 C5 Cl1 118.7(2) . . ? C7 C6 C5 119.9(2) . . ? C7 C6 H6A 120.0 . . ? C5 C6 H6A 120.0 . . ? C6 C7 C8 118.2(2) . . ? C6 C7 H7A 120.9 . . ? C8 C7 H7A 120.9 . . ? N1 C8 C7 130.6(2) . . ? N1 C8 C3 107.7(2) . . ? C7 C8 C3 121.6(3) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 C2 114.6(2) . . ? C13 C11 H11A 108.6 . . ? C2 C11 H11A 108.6 . . ? C13 C11 H11B 108.6 . . ? C2 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C13 C12 N2 110.0(2) . . ? C13 C12 C21 129.3(2) . . ? N2 C12 C21 120.7(2) . . ? C12 C13 C14 106.5(2) . . ? C12 C13 C11 127.9(2) . . ? C14 C13 C11 125.6(2) . . ? C15 C14 C19 119.1(2) . . ? C15 C14 C13 133.7(2) . . ? C19 C14 C13 107.2(2) . . ? C16 C15 C14 117.7(2) . . ? C16 C15 H15A 121.2 . . ? C14 C15 H15A 121.2 . . ? C15 C16 C17 123.2(2) . . ? C15 C16 Cl2 119.0(2) . . ? C17 C16 Cl2 117.83(19) . . ? C18 C17 C16 120.0(2) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C19 117.8(2) . . ? C17 C18 H18A 121.1 . . ? C19 C18 H18A 121.1 . . ? N2 C19 C18 129.9(2) . . ? N2 C19 C14 107.8(2) . . ? C18 C19 C14 122.2(2) . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C5 1.754(3) . ? Cl2 C16 1.749(3) . ? N1 C8 1.370(4) . ? N1 C1 1.396(4) . ? N1 C9 1.453(3) . ? N2 C19 1.375(3) . ? N2 C12 1.389(3) . ? N2 C20 1.457(3) . ? C1 C2 1.368(4) . ? C1 C10 1.493(4) . ? C2 C3 1.433(4) . ? C2 C11 1.506(4) . ? C3 C4 1.396(4) . ? C3 C8 1.421(4) . ? C4 C5 1.377(4) . ? C4 H4A 0.9500 . ? C5 C6 1.402(4) . ? C6 C7 1.380(4) . ? C6 H6A 0.9500 . ? C7 C8 1.398(4) . ? C7 H7A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C13 1.503(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.374(4) . ? C12 C21 1.498(4) . ? C13 C14 1.431(3) . ? C14 C15 1.407(3) . ? C14 C19 1.417(3) . ? C15 C16 1.377(4) . ? C15 H15A 0.9500 . ? C16 C17 1.402(4) . ? C17 C18 1.380(4) . ? C17 H17A 0.9500 . ? C18 C19 1.399(4) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 C8 N1 C1 C2 1.1(3) . . . . ? C9 N1 C1 C2 -176.9(2) . . . . ? C8 N1 C1 C10 -178.9(2) . . . . ? C9 N1 C1 C10 3.0(4) . . . . ? N1 C1 C2 C3 -1.2(3) . . . . ? C10 C1 C2 C3 178.8(3) . . . . ? N1 C1 C2 C11 -178.8(2) . . . . ? C10 C1 C2 C11 1.3(5) . . . . ? C1 C2 C3 C4 -176.2(3) . . . . ? C11 C2 C3 C4 1.5(4) . . . . ? C1 C2 C3 C8 0.8(3) . . . . ? C11 C2 C3 C8 178.5(2) . . . . ? C8 C3 C4 C5 -0.3(4) . . . . ? C2 C3 C4 C5 176.4(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C3 C4 C5 Cl1 179.25(18) . . . . ? C4 C5 C6 C7 0.2(4) . . . . ? Cl1 C5 C6 C7 -178.9(2) . . . . ? C5 C6 C7 C8 -0.5(4) . . . . ? C1 N1 C8 C7 176.4(3) . . . . ? C9 N1 C8 C7 -5.5(4) . . . . ? C1 N1 C8 C3 -0.6(3) . . . . ? C9 N1 C8 C3 177.5(2) . . . . ? C6 C7 C8 N1 -176.3(3) . . . . ? C6 C7 C8 C3 0.3(4) . . . . ? C4 C3 C8 N1 177.3(2) . . . . ? C2 C3 C8 N1 -0.2(3) . . . . ? C4 C3 C8 C7 0.0(4) . . . . ? C2 C3 C8 C7 -177.5(2) . . . . ? C1 C2 C11 C13 -113.6(3) . . . . ? C3 C2 C11 C13 69.2(3) . . . . ? C19 N2 C12 C13 0.9(3) . . . . ? C20 N2 C12 C13 178.4(2) . . . . ? C19 N2 C12 C21 -178.2(2) . . . . ? C20 N2 C12 C21 -0.8(4) . . . . ? N2 C12 C13 C14 -0.7(3) . . . . ? C21 C12 C13 C14 178.4(2) . . . . ? N2 C12 C13 C11 -178.3(2) . . . . ? C21 C12 C13 C11 0.8(4) . . . . ? C2 C11 C13 C12 -110.6(3) . . . . ? C2 C11 C13 C14 72.3(3) . . . . ? C12 C13 C14 C15 -178.2(3) . . . . ? C11 C13 C14 C15 -0.5(4) . . . . ? C12 C13 C14 C19 0.1(3) . . . . ? C11 C13 C14 C19 177.8(2) . . . . ? C19 C14 C15 C16 0.3(3) . . . . ? C13 C14 C15 C16 178.5(2) . . . . ? C14 C15 C16 C17 -0.4(4) . . . . ? C14 C15 C16 Cl2 179.13(18) . . . . ? C15 C16 C17 C18 0.1(4) . . . . ? Cl2 C16 C17 C18 -179.45(19) . . . . ? C16 C17 C18 C19 0.3(4) . . . . ? C12 N2 C19 C18 178.0(2) . . . . ? C20 N2 C19 C18 0.5(4) . . . . ? C12 N2 C19 C14 -0.8(3) . . . . ? C20 N2 C19 C14 -178.3(2) . . . . ? C17 C18 C19 N2 -179.1(2) . . . . ? C17 C18 C19 C14 -0.4(4) . . . . ? C15 C14 C19 N2 179.0(2) . . . . ? C13 C14 C19 N2 0.4(3) . . . . ? C15 C14 C19 C18 0.1(4) . . . . ? C13 C14 C19 C18 -178.5(2) . . . . ?