#------------------------------------------------------------------------------ #$Date: 2021-09-24 03:49:22 +0300 (Fri, 24 Sep 2021) $ #$Revision: 269280 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158315.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_7158315 loop_ _publ_author_name 'Tang, Zhicong' 'Hong, Gang' 'Hu, Chen' 'Wang, Qi' 'Zhong, Yi' 'Gong, Yu' 'Yang, Peng' 'Wang, Limin' _publ_section_title ; La(OTf)3 facilitated self-condensation of 2-indolylmethanol: construction of highly substituted indeno[1,2-b]indoles ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01517F _journal_year 2021 _chemical_formula_moiety 'C H2 Cl2, C42 H28 Cl2 N2' _chemical_formula_sum 'C43 H30 Cl4 N2' _chemical_formula_weight 716.49 _chemical_melting_point 452(7) _chemical_name_systematic (S)-6-(2-benzhydryl-5-chloro-1H-indol-3-yl)-2-chloro-6-phenyl-5,6-dihydroindeno[2,1-b]indole _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-03-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-07-10 deposited with the CCDC. 2021-09-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.3160(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.9191(4) _cell_length_b 12.8360(4) _cell_length_c 20.3504(6) _cell_measurement_reflns_used 9930 _cell_measurement_temperature 193(2) _cell_measurement_theta_max 54.98 _cell_measurement_theta_min 4.16 _cell_volume 3489.49(18) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 193 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0572 _diffrn_reflns_av_unetI/netI 0.0431 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 30275 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 54.966 _diffrn_reflns_theta_min 2.996 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.186 _exptl_absorpt_correction_T_max 0.7508 _exptl_absorpt_correction_T_min 0.5394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1327 before and 0.0795 after correction. The Ratio of minimum to maximum transmission is 0.7184. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.364 _exptl_crystal_description block _exptl_crystal_F_000 1480 _exptl_crystal_preparation fluorescence _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM/n-hexane=1:1' _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.722 _refine_diff_density_min -0.726 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 442 _refine_ls_number_reflns 6596 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0497 _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^)+(0.0592P)^2^+2.4121P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1263 _refine_ls_wR_factor_ref 0.1325 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5690 _reflns_number_total 6596 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01517f2.cif _cod_data_source_block mj21120_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '445-458' was changed to '452(7)' -- the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7158315 _shelx_shelxl_version_number 2016/6 _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 0.899 _shelx_estimated_absorpt_t_min 0.862 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Ternary CH refined with riding coordinates: C19(H19) 2.b Secondary CH2 refined with riding coordinates: C1(H1A,H1B) 2.c Aromatic/amide H refined with riding coordinates: N1(H1), N2(H2), C3(H3), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43) ; _shelx_res_file ; TITL mj21120_0m_a.res in P2(1)/n mj21120_0m.res created by SHELXL-2016/6 at 09:35:33 on 11-Mar-2021 REM Old TITL mj21120_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.212, Rweak 0.015, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C43 N2 Cl4 CELL 1.34139 13.9191 12.836 20.3504 90 106.316 90 ZERR 4 0.0004 0.0004 0.0006 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N DISP C 0.0148 0.007 57.7477 DISP Cl 0.3294 0.5404 4086.1782 DISP H -0 0 0.6481 DISP N 0.0253 0.0136 110.5121 UNIT 172 120 16 8 L.S. 4 PLAN 20 SIZE 0.05 0.06 0.07 TEMP -80.15 BOND $H list 4 fmap 2 acta REM REM REM WGHT 0.059200 2.412100 FVAR 0.68160 CL1 3 0.604311 0.516670 0.175317 11.00000 0.05906 0.19836 = 0.04241 0.02076 0.01641 -0.01893 CL2 3 0.404728 0.516061 0.084160 11.00000 0.07780 0.12582 = 0.09150 0.03510 -0.02412 -0.03984 C1 1 0.528800 0.486525 0.095628 11.00000 0.10123 0.08599 = 0.07542 -0.03246 0.02435 -0.03111 AFIX 23 H1A 2 0.534800 0.411082 0.087471 11.00000 -1.20000 H1B 2 0.552846 0.524683 0.061028 11.00000 -1.20000 AFIX 0 CL3 3 0.484399 0.167974 0.767271 11.00000 0.05023 0.06971 = 0.03849 0.01101 0.02477 -0.00096 CL4 3 0.333603 0.072682 0.279570 11.00000 0.04970 0.04626 = 0.08949 0.00442 -0.02455 -0.01415 N1 4 0.660975 0.354328 0.566369 11.00000 0.03590 0.02685 = 0.02598 -0.00054 0.01219 -0.00138 AFIX 43 H1 2 0.678834 0.418012 0.558894 11.00000 -1.20000 AFIX 0 N2 4 0.592279 0.436662 0.329955 11.00000 0.03585 0.03126 = 0.02749 0.00541 0.00572 -0.00016 AFIX 43 H2 2 0.589340 0.497277 0.309279 11.00000 -1.20000 AFIX 0 C2 1 0.537736 0.227246 0.708677 11.00000 0.03079 0.05158 = 0.02700 0.00791 0.01077 0.00221 C3 1 0.557416 0.166387 0.658177 11.00000 0.03298 0.03881 = 0.03234 0.00548 0.01128 0.00036 AFIX 43 H3 2 0.542189 0.094095 0.654906 11.00000 -1.20000 AFIX 0 C4 1 0.600690 0.215097 0.611874 11.00000 0.02817 0.03521 = 0.02536 0.00308 0.00737 0.00152 C5 1 0.619985 0.323678 0.618095 11.00000 0.02614 0.03514 = 0.02340 0.00158 0.00692 0.00085 C6 1 0.668573 0.267611 0.529126 11.00000 0.02868 0.02947 = 0.02385 0.00029 0.00753 0.00083 C7 1 0.633671 0.181627 0.554380 11.00000 0.02907 0.02969 = 0.02653 0.00190 0.00922 0.00030 C8 1 0.647034 0.090863 0.514412 11.00000 0.02804 0.03228 = 0.02826 0.00073 0.00700 0.00083 C9 1 0.687710 0.126950 0.462500 11.00000 0.02468 0.02839 = 0.02526 0.00127 0.00363 0.00013 C10 1 0.707004 0.246156 0.467885 11.00000 0.02755 0.02887 = 0.02168 0.00034 0.00661 -0.00054 C11 1 0.647292 0.307490 0.405086 11.00000 0.02537 0.02987 = 0.02158 -0.00054 0.00828 0.00166 C12 1 0.666929 0.406683 0.386867 11.00000 0.02953 0.03088 = 0.02304 0.00047 0.00781 0.00111 C13 1 0.523250 0.358545 0.310155 11.00000 0.03159 0.03434 = 0.02491 -0.00137 0.00875 0.00158 C14 1 0.554144 0.275256 0.356611 11.00000 0.02718 0.03189 = 0.02250 -0.00208 0.00878 0.00230 C15 1 0.494242 0.185503 0.347066 11.00000 0.03116 0.03179 = 0.03317 -0.00097 0.00545 0.00144 AFIX 43 H15 2 0.511692 0.127917 0.377414 11.00000 -1.20000 AFIX 0 C16 1 0.409105 0.183454 0.292177 11.00000 0.03266 0.03719 = 0.04235 -0.00708 0.00293 -0.00152 C17 1 0.379742 0.266472 0.246249 11.00000 0.03373 0.04755 = 0.02993 -0.00506 -0.00202 0.00366 AFIX 43 H17 2 0.320488 0.261382 0.209250 11.00000 -1.20000 AFIX 0 C18 1 0.436924 0.355175 0.254927 11.00000 0.03817 0.04100 = 0.02616 0.00348 0.00345 0.00464 AFIX 43 H18 2 0.418409 0.412405 0.224380 11.00000 -1.20000 AFIX 0 C19 1 0.747555 0.484816 0.420013 11.00000 0.03077 0.02809 = 0.02750 0.00176 0.00975 -0.00107 AFIX 13 H19 2 0.809719 0.443827 0.440964 11.00000 -1.20000 AFIX 0 C20 1 0.771388 0.556721 0.366429 11.00000 0.03128 0.03310 = 0.02811 -0.00083 0.00922 -0.00581 C21 1 0.734630 0.656715 0.353674 11.00000 0.03818 0.03730 = 0.03689 0.00432 0.01442 0.00009 AFIX 43 H21 2 0.692225 0.684005 0.378814 11.00000 -1.20000 AFIX 0 C22 1 0.759153 0.718099 0.304215 11.00000 0.04588 0.03709 = 0.03943 0.00900 0.01104 -0.00306 AFIX 43 H22 2 0.733663 0.787001 0.296084 11.00000 -1.20000 AFIX 0 C23 1 0.819996 0.679567 0.267123 11.00000 0.04787 0.05119 = 0.02923 0.00383 0.01231 -0.01408 AFIX 43 H23 2 0.837143 0.721851 0.233795 11.00000 -1.20000 AFIX 0 C24 1 0.855749 0.579697 0.278565 11.00000 0.05374 0.05386 = 0.03973 -0.00268 0.02525 -0.00541 AFIX 43 H24 2 0.896822 0.552224 0.252516 11.00000 -1.20000 AFIX 0 C25 1 0.832101 0.518743 0.328048 11.00000 0.05119 0.03877 = 0.04222 -0.00058 0.02398 0.00127 AFIX 43 H25 2 0.857799 0.449885 0.335868 11.00000 -1.20000 AFIX 0 C26 1 0.722387 0.542826 0.478394 11.00000 0.03491 0.02644 = 0.02913 0.00202 0.01140 -0.00491 C27 1 0.797108 0.560681 0.539021 11.00000 0.03388 0.04719 = 0.03488 -0.00171 0.00934 -0.00778 AFIX 43 H27 2 0.863630 0.538437 0.543113 11.00000 -1.20000 AFIX 0 C28 1 0.775276 0.610803 0.593684 11.00000 0.05210 0.06222 = 0.03374 -0.01228 0.00856 -0.01503 AFIX 43 H28 2 0.826706 0.621985 0.635027 11.00000 -1.20000 AFIX 0 C29 1 0.679082 0.644345 0.588028 11.00000 0.05999 0.05123 = 0.04037 -0.01078 0.02261 -0.00536 AFIX 43 H29 2 0.664421 0.678750 0.625406 11.00000 -1.20000 AFIX 0 C30 1 0.604342 0.627957 0.528217 11.00000 0.04547 0.04402 = 0.04501 -0.00232 0.01860 0.00398 AFIX 43 H30 2 0.538262 0.651605 0.524189 11.00000 -1.20000 AFIX 0 C31 1 0.625599 0.576842 0.473783 11.00000 0.03686 0.03810 = 0.03166 0.00072 0.00889 0.00215 AFIX 43 H31 2 0.573519 0.564913 0.432891 11.00000 -1.20000 AFIX 0 C32 1 0.820699 0.261639 0.483428 11.00000 0.02791 0.02441 = 0.02828 0.00285 0.00608 0.00026 C33 1 0.867010 0.252960 0.431363 11.00000 0.03110 0.03408 = 0.03079 0.00035 0.00802 0.00195 AFIX 43 H33 2 0.827331 0.241541 0.385674 11.00000 -1.20000 AFIX 0 C34 1 0.970039 0.260688 0.445005 11.00000 0.03361 0.04199 = 0.04826 0.00494 0.01693 0.00142 AFIX 43 H34 2 1.000413 0.254413 0.408817 11.00000 -1.20000 AFIX 0 C35 1 1.028637 0.277513 0.511190 11.00000 0.02725 0.05410 = 0.05956 0.00561 0.00741 -0.00602 AFIX 43 H35 2 1.099321 0.282437 0.520679 11.00000 -1.20000 AFIX 0 C36 1 0.984227 0.287068 0.563119 11.00000 0.03406 0.06023 = 0.03907 -0.00073 -0.00380 -0.00780 AFIX 43 H36 2 1.024339 0.299375 0.608585 11.00000 -1.20000 AFIX 0 C37 1 0.880381 0.278826 0.549614 11.00000 0.03427 0.04439 = 0.02935 -0.00042 0.00504 -0.00300 AFIX 43 H37 2 0.850441 0.285039 0.586023 11.00000 -1.20000 AFIX 0 C38 1 0.708814 0.058075 0.416340 11.00000 0.03250 0.03406 = 0.02871 -0.00265 0.00758 0.00004 AFIX 43 H38 2 0.736026 0.082299 0.381236 11.00000 -1.20000 AFIX 0 C39 1 0.689533 -0.047684 0.422076 11.00000 0.04441 0.03322 = 0.04116 -0.00928 0.01073 -0.00062 AFIX 43 H39 2 0.702970 -0.095767 0.390283 11.00000 -1.20000 AFIX 0 C40 1 0.651059 -0.083069 0.473611 11.00000 0.05181 0.02797 = 0.05287 -0.00277 0.01601 -0.00494 AFIX 43 H40 2 0.639336 -0.155461 0.477279 11.00000 -1.20000 AFIX 0 C41 1 0.629278 -0.014290 0.520134 11.00000 0.04321 0.03349 = 0.04215 0.00422 0.01536 -0.00449 AFIX 43 H41 2 0.602590 -0.039098 0.555349 11.00000 -1.20000 AFIX 0 C42 1 0.599709 0.383662 0.669582 11.00000 0.03383 0.03862 = 0.02822 -0.00272 0.00765 0.00149 AFIX 43 H42 2 0.613554 0.456245 0.673067 11.00000 -1.20000 AFIX 0 C43 1 0.558689 0.333652 0.715425 11.00000 0.03477 0.05137 = 0.02675 -0.00251 0.01074 0.00459 AFIX 43 H43 2 0.544698 0.371820 0.751663 11.00000 -1.20000 AFIX 0 HKLF 4 REM mj21120_0m_a.res in P2(1)/n REM R1 = 0.0497 for 5690 Fo > 4sig(Fo) and 0.0574 for all 6596 data REM 442 parameters refined using 0 restraints END WGHT 0.0592 2.4116 REM Highest difference peak 0.722, deepest hole -0.726, 1-sigma level 0.052 Q1 1 0.5670 0.4729 0.1442 11.00000 0.05 0.72 Q2 1 0.3629 0.5678 0.1152 11.00000 0.05 0.51 Q3 1 0.5263 0.4233 0.1222 11.00000 0.05 0.36 Q4 1 0.6026 0.5467 0.1802 11.00000 0.05 0.33 Q5 1 0.4042 0.5136 0.0635 11.00000 0.05 0.26 Q6 1 0.6042 0.2848 0.3816 11.00000 0.05 0.24 Q7 1 0.6761 0.2790 0.4325 11.00000 0.05 0.24 Q8 1 0.6050 0.2676 0.6131 11.00000 0.05 0.22 Q9 1 0.4581 0.1787 0.3129 11.00000 0.05 0.21 Q10 1 0.3555 0.0849 0.2408 11.00000 0.05 0.21 Q11 1 0.6996 0.1822 0.4611 11.00000 0.05 0.21 Q12 1 0.4822 0.3609 0.2888 11.00000 0.05 0.21 Q13 1 0.6445 0.1298 0.5414 11.00000 0.05 0.20 Q14 1 0.6014 0.3541 0.6392 11.00000 0.05 0.20 Q15 1 0.6718 0.3479 0.3846 11.00000 0.05 0.20 Q16 1 0.6398 0.4244 0.3654 11.00000 0.05 0.19 Q17 1 0.7541 0.5251 0.3883 11.00000 0.05 0.19 Q18 1 0.7143 0.4409 0.4086 11.00000 0.05 0.18 Q19 1 0.5464 0.3058 0.3251 11.00000 0.05 0.18 Q20 1 0.5599 0.1253 0.7967 11.00000 0.05 0.18 ; _shelx_res_checksum 92026 _olex2_submission_special_instructions 'No special instructions were received' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.60431(6) 0.51667(11) 0.17532(4) 0.0995(4) Uani 1 1 d . . . . . Cl2 Cl 0.40473(7) 0.51606(9) 0.08416(5) 0.1081(4) Uani 1 1 d . . . . . C1 C 0.5288(3) 0.4865(3) 0.09563(19) 0.0876(11) Uani 1 1 d . . . . . H1A H 0.534800 0.411082 0.087471 0.105 Uiso 1 1 calc R . . . . H1B H 0.552846 0.524683 0.061028 0.105 Uiso 1 1 calc R . . . . Cl3 Cl 0.48440(4) 0.16797(5) 0.76727(3) 0.05031(18) Uani 1 1 d . . . . . Cl4 Cl 0.33360(5) 0.07268(5) 0.27957(4) 0.0708(3) Uani 1 1 d . . . . . N1 N 0.66097(12) 0.35433(13) 0.56637(8) 0.0289(4) Uani 1 1 d . . . . . H1 H 0.678834 0.418012 0.558894 0.035 Uiso 1 1 calc R . . . . N2 N 0.59228(12) 0.43666(14) 0.32995(8) 0.0322(4) Uani 1 1 d . . . . . H2 H 0.589340 0.497277 0.309279 0.039 Uiso 1 1 calc R . . . . C2 C 0.53774(15) 0.22725(19) 0.70868(10) 0.0359(5) Uani 1 1 d . . . . . C3 C 0.55742(15) 0.16639(18) 0.65818(10) 0.0343(5) Uani 1 1 d . . . . . H3 H 0.542189 0.094095 0.654906 0.041 Uiso 1 1 calc R . . . . C4 C 0.60069(14) 0.21510(16) 0.61187(9) 0.0296(4) Uani 1 1 d . . . . . C5 C 0.61999(13) 0.32368(16) 0.61810(9) 0.0282(4) Uani 1 1 d . . . . . C6 C 0.66857(14) 0.26761(15) 0.52913(9) 0.0273(4) Uani 1 1 d . . . . . C7 C 0.63367(14) 0.18163(16) 0.55438(10) 0.0281(4) Uani 1 1 d . . . . . C8 C 0.64703(14) 0.09086(16) 0.51441(10) 0.0297(4) Uani 1 1 d . . . . . C9 C 0.68771(13) 0.12695(15) 0.46250(9) 0.0268(4) Uani 1 1 d . . . . . C10 C 0.70700(13) 0.24616(15) 0.46789(9) 0.0261(4) Uani 1 1 d . . . . . C11 C 0.64729(13) 0.30749(15) 0.40509(9) 0.0253(4) Uani 1 1 d . . . . . C12 C 0.66693(14) 0.40668(16) 0.38687(9) 0.0277(4) Uani 1 1 d . . . . . C13 C 0.52325(14) 0.35855(16) 0.31015(10) 0.0301(4) Uani 1 1 d . . . . . C14 C 0.55414(13) 0.27526(16) 0.35661(9) 0.0268(4) Uani 1 1 d . . . . . C15 C 0.49424(14) 0.18550(17) 0.34707(10) 0.0328(4) Uani 1 1 d . . . . . H15 H 0.511692 0.127917 0.377414 0.039 Uiso 1 1 calc R . . . . C16 C 0.40911(15) 0.18345(18) 0.29218(11) 0.0389(5) Uani 1 1 d . . . . . C17 C 0.37974(16) 0.26647(19) 0.24625(11) 0.0393(5) Uani 1 1 d . . . . . H17 H 0.320488 0.261382 0.209250 0.047 Uiso 1 1 calc R . . . . C18 C 0.43692(15) 0.35517(18) 0.25493(10) 0.0362(5) Uani 1 1 d . . . . . H18 H 0.418409 0.412405 0.224380 0.043 Uiso 1 1 calc R . . . . C19 C 0.74756(14) 0.48482(15) 0.42001(9) 0.0285(4) Uani 1 1 d . . . . . H19 H 0.809719 0.443827 0.440964 0.034 Uiso 1 1 calc R . . . . C20 C 0.77139(14) 0.55672(16) 0.36643(10) 0.0307(4) Uani 1 1 d . . . . . C21 C 0.73463(16) 0.65671(17) 0.35367(11) 0.0367(5) Uani 1 1 d . . . . . H21 H 0.692225 0.684005 0.378814 0.044 Uiso 1 1 calc R . . . . C22 C 0.75915(17) 0.71810(19) 0.30422(11) 0.0410(5) Uani 1 1 d . . . . . H22 H 0.733663 0.787001 0.296084 0.049 Uiso 1 1 calc R . . . . C23 C 0.82000(17) 0.6796(2) 0.26712(11) 0.0425(5) Uani 1 1 d . . . . . H23 H 0.837143 0.721851 0.233795 0.051 Uiso 1 1 calc R . . . . C24 C 0.85575(19) 0.5797(2) 0.27857(12) 0.0466(6) Uani 1 1 d . . . . . H24 H 0.896822 0.552224 0.252516 0.056 Uiso 1 1 calc R . . . . C25 C 0.83210(18) 0.51874(19) 0.32805(12) 0.0419(5) Uani 1 1 d . . . . . H25 H 0.857799 0.449885 0.335868 0.050 Uiso 1 1 calc R . . . . C26 C 0.72239(14) 0.54283(16) 0.47839(10) 0.0297(4) Uani 1 1 d . . . . . C27 C 0.79711(16) 0.56068(18) 0.53902(11) 0.0387(5) Uani 1 1 d . . . . . H27 H 0.863630 0.538437 0.543113 0.046 Uiso 1 1 calc R . . . . C28 C 0.77528(19) 0.6108(2) 0.59368(12) 0.0501(6) Uani 1 1 d . . . . . H28 H 0.826706 0.621985 0.635027 0.060 Uiso 1 1 calc R . . . . C29 C 0.67908(19) 0.6443(2) 0.58803(12) 0.0488(6) Uani 1 1 d . . . . . H29 H 0.664421 0.678750 0.625406 0.059 Uiso 1 1 calc R . . . . C30 C 0.60434(18) 0.62796(19) 0.52822(12) 0.0436(5) Uani 1 1 d . . . . . H30 H 0.538262 0.651605 0.524189 0.052 Uiso 1 1 calc R . . . . C31 C 0.62560(16) 0.57684(17) 0.47378(11) 0.0357(5) Uani 1 1 d . . . . . H31 H 0.573519 0.564913 0.432891 0.043 Uiso 1 1 calc R . . . . C32 C 0.82070(13) 0.26164(15) 0.48343(10) 0.0272(4) Uani 1 1 d . . . . . C33 C 0.86701(14) 0.25296(16) 0.43136(10) 0.0321(4) Uani 1 1 d . . . . . H33 H 0.827331 0.241541 0.385674 0.039 Uiso 1 1 calc R . . . . C34 C 0.97004(16) 0.26069(18) 0.44500(12) 0.0402(5) Uani 1 1 d . . . . . H34 H 1.000413 0.254413 0.408817 0.048 Uiso 1 1 calc R . . . . C35 C 1.02864(16) 0.2775(2) 0.51119(13) 0.0479(6) Uani 1 1 d . . . . . H35 H 1.099321 0.282437 0.520679 0.058 Uiso 1 1 calc R . . . . C36 C 0.98423(16) 0.2871(2) 0.56312(12) 0.0473(6) Uani 1 1 d . . . . . H36 H 1.024339 0.299375 0.608585 0.057 Uiso 1 1 calc R . . . . C37 C 0.88038(15) 0.27883(18) 0.54961(11) 0.0368(5) Uani 1 1 d . . . . . H37 H 0.850441 0.285039 0.586023 0.044 Uiso 1 1 calc R . . . . C38 C 0.70881(14) 0.05807(16) 0.41634(10) 0.0320(4) Uani 1 1 d . . . . . H38 H 0.736026 0.082299 0.381236 0.038 Uiso 1 1 calc R . . . . C39 C 0.68953(17) -0.04768(18) 0.42208(11) 0.0399(5) Uani 1 1 d . . . . . H39 H 0.702970 -0.095767 0.390283 0.048 Uiso 1 1 calc R . . . . C40 C 0.65106(18) -0.08307(18) 0.47361(12) 0.0440(5) Uani 1 1 d . . . . . H40 H 0.639336 -0.155461 0.477279 0.053 Uiso 1 1 calc R . . . . C41 C 0.62928(16) -0.01429(17) 0.52013(12) 0.0389(5) Uani 1 1 d . . . . . H41 H 0.602590 -0.039098 0.555349 0.047 Uiso 1 1 calc R . . . . C42 C 0.59971(15) 0.38366(18) 0.66958(10) 0.0338(4) Uani 1 1 d . . . . . H42 H 0.613554 0.456245 0.673067 0.041 Uiso 1 1 calc R . . . . C43 C 0.55869(15) 0.33365(19) 0.71542(10) 0.0372(5) Uani 1 1 d . . . . . H43 H 0.544698 0.371820 0.751663 0.045 Uiso 1 1 calc R . . . . 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 0.0591(4) 0.1984(12) 0.0424(4) 0.0208(5) 0.0164(3) -0.0189(6) Cl2 0.0778(6) 0.1258(9) 0.0915(7) 0.0351(6) -0.0241(5) -0.0398(6) C1 0.101(3) 0.086(3) 0.075(2) -0.0325(19) 0.024(2) -0.031(2) Cl3 0.0502(3) 0.0697(4) 0.0385(3) 0.0110(3) 0.0248(2) -0.0010(3) Cl4 0.0497(4) 0.0463(4) 0.0895(5) 0.0044(3) -0.0246(3) -0.0141(3) N1 0.0359(8) 0.0269(9) 0.0260(8) -0.0005(7) 0.0122(6) -0.0014(7) N2 0.0358(9) 0.0313(10) 0.0275(8) 0.0054(7) 0.0057(7) -0.0002(7) C2 0.0308(10) 0.0516(14) 0.0270(10) 0.0079(9) 0.0108(8) 0.0022(9) C3 0.0330(10) 0.0388(12) 0.0323(10) 0.0055(9) 0.0113(8) 0.0004(9) C4 0.0282(9) 0.0352(11) 0.0254(9) 0.0031(8) 0.0074(7) 0.0015(8) C5 0.0261(9) 0.0351(11) 0.0234(9) 0.0016(8) 0.0069(7) 0.0008(8) C6 0.0287(9) 0.0295(11) 0.0239(9) 0.0003(8) 0.0075(7) 0.0008(8) C7 0.0291(9) 0.0297(11) 0.0265(9) 0.0019(8) 0.0092(7) 0.0003(8) C8 0.0280(9) 0.0323(11) 0.0283(9) 0.0007(8) 0.0070(7) 0.0008(8) C9 0.0247(8) 0.0284(10) 0.0253(9) 0.0013(7) 0.0036(7) 0.0001(7) C10 0.0276(9) 0.0289(10) 0.0217(9) 0.0003(7) 0.0066(7) -0.0005(7) C11 0.0254(8) 0.0299(10) 0.0216(9) -0.0005(7) 0.0083(7) 0.0017(7) C12 0.0295(9) 0.0309(11) 0.0230(9) 0.0005(8) 0.0078(7) 0.0011(8) C13 0.0316(9) 0.0343(11) 0.0249(9) -0.0014(8) 0.0087(7) 0.0016(8) C14 0.0272(9) 0.0319(11) 0.0225(9) -0.0021(7) 0.0088(7) 0.0023(8) C15 0.0312(10) 0.0318(11) 0.0332(10) -0.0010(8) 0.0055(8) 0.0014(8) C16 0.0327(10) 0.0372(13) 0.0423(12) -0.0071(10) 0.0029(9) -0.0015(9) C17 0.0337(10) 0.0476(14) 0.0299(10) -0.0051(9) -0.0020(8) 0.0037(9) C18 0.0382(11) 0.0410(13) 0.0262(10) 0.0035(9) 0.0035(8) 0.0046(9) C19 0.0308(9) 0.0281(11) 0.0275(9) 0.0018(8) 0.0098(8) -0.0011(8) C20 0.0313(10) 0.0331(12) 0.0281(10) -0.0008(8) 0.0092(8) -0.0058(8) C21 0.0382(11) 0.0373(12) 0.0369(11) 0.0043(9) 0.0144(9) 0.0001(9) C22 0.0459(12) 0.0371(13) 0.0394(12) 0.0090(10) 0.0110(9) -0.0031(10) C23 0.0479(12) 0.0512(15) 0.0292(11) 0.0038(10) 0.0123(9) -0.0141(11) C24 0.0537(13) 0.0539(16) 0.0397(12) -0.0027(11) 0.0253(11) -0.0054(11) C25 0.0512(13) 0.0388(13) 0.0422(12) -0.0006(10) 0.0240(10) 0.0013(10) C26 0.0349(10) 0.0264(10) 0.0291(10) 0.0020(8) 0.0114(8) -0.0049(8) C27 0.0339(10) 0.0472(14) 0.0349(11) -0.0017(9) 0.0093(9) -0.0078(9) C28 0.0521(14) 0.0622(17) 0.0337(12) -0.0123(11) 0.0086(10) -0.0150(12) C29 0.0600(15) 0.0512(15) 0.0404(12) -0.0108(11) 0.0226(11) -0.0054(12) C30 0.0455(12) 0.0440(14) 0.0450(13) -0.0023(10) 0.0186(10) 0.0040(10) C31 0.0369(10) 0.0381(12) 0.0317(10) 0.0007(9) 0.0089(8) 0.0021(9) C32 0.0279(9) 0.0244(10) 0.0283(9) 0.0028(7) 0.0061(7) 0.0003(7) C33 0.0311(10) 0.0341(12) 0.0308(10) 0.0004(8) 0.0080(8) 0.0020(8) C34 0.0336(10) 0.0420(13) 0.0483(13) 0.0049(10) 0.0169(9) 0.0014(9) C35 0.0272(10) 0.0541(16) 0.0596(15) 0.0056(12) 0.0074(10) -0.0060(10) C36 0.0341(11) 0.0602(16) 0.0391(12) -0.0007(11) -0.0038(9) -0.0078(10) C37 0.0343(10) 0.0444(13) 0.0294(10) -0.0004(9) 0.0050(8) -0.0030(9) C38 0.0325(10) 0.0341(12) 0.0287(10) -0.0026(8) 0.0076(8) 0.0000(8) C39 0.0444(12) 0.0332(12) 0.0412(12) -0.0093(9) 0.0107(9) -0.0006(9) C40 0.0518(13) 0.0280(12) 0.0529(14) -0.0028(10) 0.0160(11) -0.0049(10) C41 0.0432(11) 0.0335(12) 0.0421(12) 0.0042(9) 0.0154(9) -0.0045(9) C42 0.0338(10) 0.0386(12) 0.0282(10) -0.0027(8) 0.0077(8) 0.0015(9) C43 0.0348(10) 0.0514(14) 0.0268(10) -0.0025(9) 0.0107(8) 0.0046(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0148 0.0070 '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 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0253 0.0136 '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 Cl1 C1 Cl2 113.9(2) . . ? Cl1 C1 H1A 108.8 . . ? Cl1 C1 H1B 108.8 . . ? Cl2 C1 H1A 108.8 . . ? Cl2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? C5 N1 H1 126.2 . . ? C6 N1 H1 126.2 . . ? C6 N1 C5 107.58(16) . . ? C12 N2 H2 124.9 . . ? C13 N2 H2 124.9 . . ? C13 N2 C12 110.16(16) . . ? C3 C2 Cl3 118.29(18) . . ? C3 C2 C43 123.25(19) . . ? C43 C2 Cl3 118.46(16) . . ? C2 C3 H3 121.2 . . ? C2 C3 C4 117.5(2) . . ? C4 C3 H3 121.2 . . ? C3 C4 C5 119.03(18) . . ? C3 C4 C7 135.3(2) . . ? C5 C4 C7 105.70(17) . . ? N1 C5 C4 108.59(17) . . ? N1 C5 C42 128.89(19) . . ? C42 C5 C4 122.52(18) . . ? N1 C6 C10 134.83(17) . . ? C7 C6 N1 111.03(17) . . ? C7 C6 C10 114.14(17) . . ? C4 C7 C8 144.14(18) . . ? C6 C7 C4 107.10(17) . . ? C6 C7 C8 108.71(17) . . ? C9 C8 C7 107.20(17) . . ? C41 C8 C7 132.61(19) . . ? C41 C8 C9 120.18(19) . . ? C8 C9 C10 111.65(16) . . ? C38 C9 C8 120.44(19) . . ? C38 C9 C10 127.86(17) . . ? C6 C10 C9 98.24(15) . . ? C6 C10 C11 111.04(15) . . ? C6 C10 C32 112.87(15) . . ? C11 C10 C9 113.90(15) . . ? C11 C10 C32 113.02(15) . . ? C32 C10 C9 106.84(15) . . ? C12 C11 C10 126.76(17) . . ? C12 C11 C14 106.74(16) . . ? C14 C11 C10 126.31(17) . . ? N2 C12 C19 118.65(17) . . ? C11 C12 N2 109.01(16) . . ? C11 C12 C19 132.19(17) . . ? N2 C13 C14 107.52(16) . . ? N2 C13 C18 129.33(19) . . ? C18 C13 C14 123.15(19) . . ? C13 C14 C11 106.57(17) . . ? C15 C14 C11 135.29(18) . . ? C15 C14 C13 118.14(17) . . ? C14 C15 H15 121.0 . . ? C16 C15 C14 118.0(2) . . ? C16 C15 H15 121.0 . . ? C15 C16 Cl4 118.62(18) . . ? C15 C16 C17 123.2(2) . . ? C17 C16 Cl4 118.13(16) . . ? C16 C17 H17 120.1 . . ? C18 C17 C16 119.71(19) . . ? C18 C17 H17 120.1 . . ? C13 C18 H18 121.1 . . ? C17 C18 C13 117.8(2) . . ? C17 C18 H18 121.1 . . ? C12 C19 H19 106.6 . . ? C12 C19 C20 111.27(15) . . ? C12 C19 C26 111.52(15) . . ? C20 C19 H19 106.6 . . ? C26 C19 H19 106.6 . . ? C26 C19 C20 113.77(16) . . ? C21 C20 C19 123.42(18) . . ? C21 C20 C25 118.20(19) . . ? C25 C20 C19 118.38(19) . . ? C20 C21 H21 119.7 . . ? C20 C21 C22 120.6(2) . . ? C22 C21 H21 119.7 . . ? C21 C22 H22 119.8 . . ? C23 C22 C21 120.4(2) . . ? C23 C22 H22 119.8 . . ? C22 C23 H23 120.2 . . ? C24 C23 C22 119.5(2) . . ? C24 C23 H23 120.2 . . ? C23 C24 H24 119.9 . . ? C23 C24 C25 120.1(2) . . ? C25 C24 H24 119.9 . . ? C20 C25 H25 119.5 . . ? C24 C25 C20 121.1(2) . . ? C24 C25 H25 119.5 . . ? C27 C26 C19 119.58(18) . . ? C27 C26 C31 118.40(19) . . ? C31 C26 C19 122.01(17) . . ? C26 C27 H27 119.7 . . ? C28 C27 C26 120.6(2) . . ? C28 C27 H27 119.7 . . ? C27 C28 H28 119.9 . . ? C29 C28 C27 120.2(2) . . ? C29 C28 H28 119.9 . . ? C28 C29 H29 120.0 . . ? C30 C29 C28 120.0(2) . . ? C30 C29 H29 120.0 . . ? C29 C30 H30 120.0 . . ? C29 C30 C31 120.0(2) . . ? C31 C30 H30 120.0 . . ? C26 C31 H31 119.6 . . ? C30 C31 C26 120.8(2) . . ? C30 C31 H31 119.6 . . ? C33 C32 C10 120.24(16) . . ? C37 C32 C10 121.43(17) . . ? C37 C32 C33 118.24(18) . . ? C32 C33 H33 119.4 . . ? C34 C33 C32 121.11(19) . . ? C34 C33 H33 119.4 . . ? C33 C34 H34 120.0 . . ? C35 C34 C33 120.1(2) . . ? C35 C34 H34 120.0 . . ? C34 C35 H35 120.2 . . ? C36 C35 C34 119.7(2) . . ? C36 C35 H35 120.2 . . ? C35 C36 H36 119.8 . . ? C35 C36 C37 120.5(2) . . ? C37 C36 H36 119.8 . . ? C32 C37 C36 120.5(2) . . ? C32 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C9 C38 H38 120.5 . . ? C9 C38 C39 118.92(19) . . ? C39 C38 H38 120.5 . . ? C38 C39 H39 119.7 . . ? C40 C39 C38 120.5(2) . . ? C40 C39 H39 119.7 . . ? C39 C40 H40 119.5 . . ? C39 C40 C41 120.9(2) . . ? C41 C40 H40 119.5 . . ? C8 C41 C40 119.0(2) . . ? C8 C41 H41 120.5 . . ? C40 C41 H41 120.5 . . ? C5 C42 H42 121.3 . . ? C43 C42 C5 117.5(2) . . ? C43 C42 H42 121.3 . . ? C2 C43 H43 119.9 . . ? C42 C43 C2 120.2(2) . . ? C42 C43 H43 119.9 . . ? 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 C1 1.711(4) . ? Cl2 C1 1.719(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? Cl3 C2 1.746(2) . ? Cl4 C16 1.744(2) . ? N1 H1 0.8800 . ? N1 C5 1.388(2) . ? N1 C6 1.367(3) . ? N2 H2 0.8800 . ? N2 C12 1.376(2) . ? N2 C13 1.369(3) . ? C2 C3 1.378(3) . ? C2 C43 1.395(3) . ? C3 H3 0.9500 . ? C3 C4 1.400(3) . ? C4 C5 1.418(3) . ? C4 C7 1.437(3) . ? C5 C42 1.392(3) . ? C6 C7 1.363(3) . ? C6 C10 1.513(3) . ? C7 C8 1.462(3) . ? C8 C9 1.410(3) . ? C8 C41 1.383(3) . ? C9 C10 1.552(3) . ? C9 C38 1.380(3) . ? C10 C11 1.532(3) . ? C10 C32 1.537(3) . ? C11 C12 1.375(3) . ? C11 C14 1.451(3) . ? C12 C19 1.515(3) . ? C13 C14 1.412(3) . ? C13 C18 1.396(3) . ? C14 C15 1.403(3) . ? C15 H15 0.9500 . ? C15 C16 1.382(3) . ? C16 C17 1.401(3) . ? C17 H17 0.9500 . ? C17 C18 1.372(3) . ? C18 H18 0.9500 . ? C19 H19 1.0000 . ? C19 C20 1.534(3) . ? C19 C26 1.524(3) . ? C20 C21 1.379(3) . ? C20 C25 1.390(3) . ? C21 H21 0.9500 . ? C21 C22 1.394(3) . ? C22 H22 0.9500 . ? C22 C23 1.375(3) . ? C23 H23 0.9500 . ? C23 C24 1.371(4) . ? C24 H24 0.9500 . ? C24 C25 1.386(3) . ? C25 H25 0.9500 . ? C26 C27 1.391(3) . ? C26 C31 1.394(3) . ? C27 H27 0.9500 . ? C27 C28 1.391(3) . ? C28 H28 0.9500 . ? C28 C29 1.380(4) . ? C29 H29 0.9500 . ? C29 C30 1.377(3) . ? C30 H30 0.9500 . ? C30 C31 1.389(3) . ? C31 H31 0.9500 . ? C32 C33 1.391(3) . ? C32 C37 1.387(3) . ? C33 H33 0.9500 . ? C33 C34 1.386(3) . ? C34 H34 0.9500 . ? C34 C35 1.382(3) . ? C35 H35 0.9500 . ? C35 C36 1.371(3) . ? C36 H36 0.9500 . ? C36 C37 1.397(3) . ? C37 H37 0.9500 . ? C38 H38 0.9500 . ? C38 C39 1.395(3) . ? C39 H39 0.9500 . ? C39 C40 1.382(3) . ? C40 H40 0.9500 . ? C40 C41 1.389(3) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C42 C43 1.381(3) . ? C43 H43 0.9500 . ?