#------------------------------------------------------------------------------ #$Date: 2022-08-06 03:26:35 +0300 (Sat, 06 Aug 2022) $ #$Revision: 277086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158810.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_7158810 loop_ _publ_author_name 'Cho, Eun Hee' 'Akhtar, Muhammad Saeed' 'Aslam, Mohammad' 'Thombal, Raju S.' 'Li, Xin' 'Shim, Jae-Jin' 'Lee, Yong Rok' _publ_section_title ; Transition Metal-Catalyzed Regioselective Functionalization of Carbazoles and Indolines with Maleimides ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D2OB01077A _journal_year 2022 _chemical_formula_moiety '2(C27 H16 Cl3 N3 O2), C3 H6 O' _chemical_formula_sum 'C57 H38 Cl6 N6 O5' _chemical_formula_weight 1099.63 _chemical_melting_point 399 _chemical_name_systematic 3-(9-(Pyridin-2-yl)-9H-carbazol-1-yl)-1-(2,4,6-trichlorophenyl)pyrrolidine-2,5-dione _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2022-06-08 deposited with the CCDC. 2022-08-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.043(19) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 31.146(18) _cell_length_b 11.338(7) _cell_length_c 15.115(9) _cell_measurement_reflns_used 8155 _cell_measurement_temperature 223(2) _cell_measurement_theta_max 24.01 _cell_measurement_theta_min 2.37 _cell_volume 5317(6) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 223(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0883 _diffrn_reflns_av_unetI/netI 0.0592 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 48713 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.522 _diffrn_reflns_theta_min 1.912 _exptl_absorpt_coefficient_mu 0.378 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6814 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.374 _exptl_crystal_description BLOCK _exptl_crystal_F_000 2256 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetone/ethylactate' _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.042 _refine_diff_density_max 2.182 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.111 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 335 _refine_ls_number_reflns 6666 _refine_ls_number_restraints 12 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0814 _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^)+(0.1673P)^2^+7.9730P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2405 _refine_ls_wR_factor_ref 0.2937 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3859 _reflns_number_total 6666 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2ob01077a2.cif _cod_data_source_block EH_83_a _cod_original_cell_volume 5317(5) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7158810 _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 0.921 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; TITL EH_83_a.res in C2/c EH_83_a.res created by SHELXL-2018/3 at 09:19:52 on 24-May-2022 REM Old TITL EH_83 in C2/c REM SHELXT solution in C2/c REM R1 0.197, Rweak 0.014, Alpha 0.031, Orientation as input REM Formula found by SHELXT: C57 Cl6 N6 O5 CELL 0.71073 31.1455 11.3381 15.1150 90.000 95.043 90.000 ZERR 4.000 0.0181 0.0070 0.0086 0.000 0.019 0.000 LATT 7 SYMM -X, Y, 1/2-Z SFAC C H CL N O UNIT 228 152 24 24 20 TEMP -50.000 SIZE 0.042 0.11 0.22 L.S. 10 BOND $H LIST 4 FMAP 2 PLAN 20 ACTA ISOR 0.005 O3 C29 C29 omit -4 0 2 omit -1 1 2 WGHT 0.167300 7.973000 FVAR 0.23896 CL1 3 0.224127 0.322792 0.357171 11.00000 0.05602 0.05594 = 0.04798 -0.01238 0.00083 -0.00483 CL2 3 0.263234 0.619120 0.632747 11.00000 0.06109 0.05564 = 0.04845 -0.01305 0.01035 -0.01344 CL3 3 0.146399 0.275980 0.658074 11.00000 0.06250 0.10176 = 0.07348 0.01998 0.01582 -0.03295 O1 5 0.331900 0.453580 0.540083 11.00000 0.04005 0.04956 = 0.06317 0.00614 -0.00851 -0.00336 O2 5 0.227830 0.607814 0.342557 11.00000 0.04023 0.05493 = 0.05025 0.00327 -0.00322 0.00026 O3 5 0.500000 0.081081 0.250000 10.50000 0.18592 0.11654 = 0.25971 0.00000 0.09559 0.00000 N1 4 0.273124 0.520112 0.451809 11.00000 0.02971 0.04315 = 0.03953 -0.00085 0.00303 -0.00398 N2 4 0.442646 0.622376 0.407503 11.00000 0.02856 0.04536 = 0.04788 -0.00630 0.00755 -0.00120 N3 4 0.407180 0.561282 0.273328 11.00000 0.04293 0.06573 = 0.04085 0.00733 0.00323 -0.00465 C1 1 0.241056 0.465007 0.499606 11.00000 0.02834 0.04247 = 0.03930 0.00044 0.00305 -0.00210 C2 1 0.215882 0.372475 0.462872 11.00000 0.03348 0.04454 = 0.04122 -0.00039 -0.00071 -0.00299 C3 1 0.185847 0.316604 0.508635 11.00000 0.04152 0.04942 = 0.05673 0.00349 -0.00078 -0.00920 AFIX 43 H3 2 0.168634 0.255822 0.482269 11.00000 -1.20000 AFIX 0 C4 1 0.181541 0.352427 0.595342 11.00000 0.04062 0.05971 = 0.05209 0.01393 0.00363 -0.00470 C5 1 0.204901 0.444895 0.634678 11.00000 0.03847 0.06556 = 0.04319 0.00092 0.00592 -0.00398 AFIX 43 H5 2 0.201031 0.468799 0.692993 11.00000 -1.20000 AFIX 0 C6 1 0.234270 0.501350 0.585293 11.00000 0.03671 0.04481 = 0.04254 -0.00044 0.00301 -0.00083 C7 1 0.317158 0.509129 0.476205 11.00000 0.03232 0.03910 = 0.04669 -0.00313 0.00299 -0.00123 C8 1 0.341373 0.574173 0.408607 11.00000 0.03169 0.04533 = 0.05167 -0.00170 0.01034 -0.00498 AFIX 13 H8 2 0.361104 0.518477 0.382108 11.00000 -1.20000 AFIX 0 C9 1 0.306107 0.612978 0.336667 11.00000 0.04452 0.07121 = 0.04261 -0.00368 0.00884 -0.01094 AFIX 23 H9A 2 0.308092 0.697834 0.325384 11.00000 -1.20000 H9AB 2 0.309021 0.570520 0.281038 11.00000 -1.20000 AFIX 0 C10 1 0.263851 0.583517 0.372710 11.00000 0.04090 0.04201 = 0.03754 -0.00469 0.00473 -0.00216 C11 1 0.367574 0.675301 0.451872 11.00000 0.03083 0.04132 = 0.04920 0.00122 0.00579 -0.00164 C12 1 0.346606 0.759817 0.499602 11.00000 0.03721 0.04573 = 0.05906 -0.00256 0.01322 -0.00099 AFIX 43 H12 2 0.316702 0.752574 0.502580 11.00000 -1.20000 AFIX 0 C13 1 0.367917 0.854850 0.543265 11.00000 0.04792 0.04668 = 0.05893 -0.00416 0.01396 0.00785 AFIX 43 H13 2 0.352309 0.910189 0.573874 11.00000 -1.20000 AFIX 0 C14 1 0.411913 0.867047 0.541233 11.00000 0.04396 0.03925 = 0.05217 -0.00357 0.00400 -0.00214 AFIX 43 H14 2 0.426638 0.929845 0.571011 11.00000 -1.20000 AFIX 0 C15 1 0.434081 0.784766 0.494337 11.00000 0.03514 0.03896 = 0.04086 0.00132 0.00484 0.00043 C16 1 0.412272 0.691286 0.448597 11.00000 0.03176 0.03863 = 0.04380 0.00413 0.00684 0.00081 C17 1 0.483338 0.672700 0.428225 11.00000 0.02984 0.04976 = 0.04881 0.00006 0.00429 -0.00198 C18 1 0.479634 0.772747 0.482128 11.00000 0.03737 0.04384 = 0.04722 -0.00008 0.00435 -0.00427 C19 1 0.515910 0.839033 0.510020 11.00000 0.04125 0.05369 = 0.05633 0.00001 0.00198 -0.00446 AFIX 43 H19 2 0.513700 0.906037 0.545963 11.00000 -1.20000 AFIX 0 C20 1 0.555036 0.804030 0.483672 11.00000 0.03950 0.06822 = 0.07609 -0.00143 0.00103 -0.01344 AFIX 43 H20 2 0.579824 0.847417 0.502981 11.00000 -1.20000 AFIX 0 C21 1 0.559143 0.706348 0.429285 11.00000 0.03114 0.07274 = 0.08705 -0.01183 0.00871 -0.00446 AFIX 43 H21 2 0.586397 0.685888 0.411802 11.00000 -1.20000 AFIX 0 C22 1 0.523133 0.638250 0.400341 11.00000 0.03418 0.06253 = 0.07126 -0.01213 0.01058 -0.00225 AFIX 43 H22 2 0.525582 0.572069 0.363665 11.00000 -1.20000 AFIX 0 C23 1 0.434983 0.534341 0.341458 11.00000 0.03430 0.04588 = 0.03742 -0.00053 0.00974 -0.00427 C24 1 0.399598 0.477597 0.210522 11.00000 0.06110 0.09401 = 0.03800 -0.00333 0.00463 -0.02831 AFIX 43 H24 2 0.379445 0.493809 0.162054 11.00000 -1.20000 AFIX 0 C25 1 0.419713 0.370495 0.213762 11.00000 0.07223 0.08587 = 0.05523 -0.03181 0.03151 -0.03831 AFIX 43 H25 2 0.413834 0.315196 0.167962 11.00000 -1.20000 AFIX 0 C26 1 0.448539 0.344925 0.284655 11.00000 0.05863 0.05204 = 0.08246 -0.01838 0.03133 -0.00646 AFIX 43 H26 2 0.462949 0.272005 0.288186 11.00000 -1.20000 AFIX 0 C27 1 0.456124 0.427914 0.350906 11.00000 0.03904 0.04847 = 0.05825 -0.00336 0.01164 0.00165 AFIX 43 H27 2 0.475226 0.412190 0.401174 11.00000 -1.20000 AFIX 0 C28 1 0.500000 -0.026235 0.250000 10.50000 0.19276 0.06055 = 0.04857 0.00000 0.02994 0.00000 C29 1 0.463772 -0.083145 0.260398 11.00000 0.12324 0.06438 = 0.10796 0.01133 -0.03660 -0.02546 AFIX 33 H29A 2 0.468941 -0.167457 0.258914 11.00000 -1.50000 H29B 2 0.453564 -0.061880 0.317072 11.00000 -1.50000 H29C 2 0.442210 -0.061880 0.212842 11.00000 -1.50000 AFIX 0 HKLF 4 REM EH_83_a.res in C2/c REM wR2 = 0.293710, GooF = S = 1.04315, Restrained GooF = 1.05874 for all data REM R1 = 0.081420 for 3859 Fo > 4sig(Fo) and 0.137843 for all 6666 data REM 335 parameters refined using 12 restraints END WGHT 0.1673 7.9910 REM Highest difference peak 2.182, deepest hole -0.620, 1-sigma level 0.111 Q1 1 0.4294 -0.0266 0.2783 11.00000 0.05 2.18 Q2 1 0.3930 -0.1037 0.2439 11.00000 0.05 2.00 Q3 1 0.4888 0.0783 0.2051 11.00000 0.05 0.94 Q4 1 0.4725 -0.0758 0.2332 11.00000 0.05 0.54 Q5 1 0.4712 -0.0763 0.2894 11.00000 0.05 0.41 Q6 1 0.5920 0.8672 0.5167 11.00000 0.05 0.28 Q7 1 0.5962 0.8768 0.4899 11.00000 0.05 0.27 Q8 1 0.1618 0.5429 0.7457 11.00000 0.05 0.26 Q9 1 0.4375 0.6421 0.4296 11.00000 0.05 0.25 Q10 1 0.4067 0.3799 0.1391 11.00000 0.05 0.22 Q11 1 0.2797 0.6011 0.3550 11.00000 0.05 0.21 Q12 1 0.4517 0.3184 0.2919 11.00000 0.05 0.21 Q13 1 0.5487 0.6908 0.4105 11.00000 0.05 0.21 Q14 1 0.2200 0.2631 0.6231 11.00000 0.05 0.20 Q15 1 0.4874 0.3024 0.3239 11.00000 0.05 0.20 Q16 1 0.5498 0.7600 0.4424 11.00000 0.05 0.20 Q17 1 0.2503 0.4765 0.7584 11.00000 0.05 0.20 Q18 1 0.3290 0.5419 0.4412 11.00000 0.05 0.20 Q19 1 0.2174 0.4401 0.6335 11.00000 0.05 0.19 Q20 1 0.2401 0.2941 0.2475 11.00000 0.05 0.19 ; _shelx_res_checksum 70094 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 0.22413(4) 0.32279(10) 0.35717(7) 0.0535(3) Uani 1 1 d . . . . . Cl2 Cl 0.26323(4) 0.61912(10) 0.63275(7) 0.0547(3) Uani 1 1 d . . . . . Cl3 Cl 0.14640(5) 0.27598(15) 0.65807(10) 0.0787(5) Uani 1 1 d . . . . . O1 O 0.33190(9) 0.4536(3) 0.5401(2) 0.0517(8) Uani 1 1 d . . . . . O2 O 0.22783(9) 0.6078(3) 0.3426(2) 0.0489(7) Uani 1 1 d . . . . . O3 O 0.500000 0.0811(9) 0.250000 0.183(4) Uani 1 2 d S TU P . . N1 N 0.27312(10) 0.5201(3) 0.4518(2) 0.0375(7) Uani 1 1 d . . . . . N2 N 0.44265(10) 0.6224(3) 0.4075(2) 0.0404(8) Uani 1 1 d . . . . . N3 N 0.40718(11) 0.5613(4) 0.2733(2) 0.0499(9) Uani 1 1 d . . . . . C1 C 0.24106(11) 0.4650(3) 0.4996(2) 0.0367(8) Uani 1 1 d . . . . . C2 C 0.21588(12) 0.3725(4) 0.4629(3) 0.0400(9) Uani 1 1 d . . . . . C3 C 0.18585(14) 0.3166(4) 0.5086(3) 0.0495(10) Uani 1 1 d . . . . . H3 H 0.168634 0.255822 0.482269 0.059 Uiso 1 1 calc R U . . . C4 C 0.18154(14) 0.3524(4) 0.5953(3) 0.0508(11) Uani 1 1 d . . . . . C5 C 0.20490(13) 0.4449(4) 0.6347(3) 0.0489(10) Uani 1 1 d . . . . . H5 H 0.201031 0.468799 0.692993 0.059 Uiso 1 1 calc R U . . . C6 C 0.23427(13) 0.5014(4) 0.5853(3) 0.0414(9) Uani 1 1 d . . . . . C7 C 0.31716(12) 0.5091(3) 0.4762(3) 0.0394(8) Uani 1 1 d . . . . . C8 C 0.34137(12) 0.5742(4) 0.4086(3) 0.0425(9) Uani 1 1 d . . . . . H8 H 0.361104 0.518477 0.382108 0.051 Uiso 1 1 calc R U . . . C9 C 0.30611(14) 0.6130(4) 0.3367(3) 0.0525(11) Uani 1 1 d . . . . . H9A H 0.308092 0.697834 0.325384 0.063 Uiso 1 1 calc R U . . . H9AB H 0.309021 0.570520 0.281038 0.063 Uiso 1 1 calc R U . . . C10 C 0.26385(13) 0.5835(4) 0.3727(3) 0.0401(9) Uani 1 1 d . . . . . C11 C 0.36757(12) 0.6753(3) 0.4519(3) 0.0403(9) Uani 1 1 d . . . . . C12 C 0.34661(13) 0.7598(4) 0.4996(3) 0.0468(10) Uani 1 1 d . . . . . H12 H 0.316702 0.752574 0.502580 0.056 Uiso 1 1 calc R U . . . C13 C 0.36792(14) 0.8549(4) 0.5433(3) 0.0506(10) Uani 1 1 d . . . . . H13 H 0.352309 0.910189 0.573874 0.061 Uiso 1 1 calc R U . . . C14 C 0.41191(14) 0.8670(4) 0.5412(3) 0.0451(9) Uani 1 1 d . . . . . H14 H 0.426638 0.929845 0.571011 0.054 Uiso 1 1 calc R U . . . C15 C 0.43408(12) 0.7848(3) 0.4943(3) 0.0382(8) Uani 1 1 d . . . . . C16 C 0.41227(12) 0.6913(3) 0.4486(3) 0.0379(8) Uani 1 1 d . . . . . C17 C 0.48334(12) 0.6727(4) 0.4282(3) 0.0428(9) Uani 1 1 d . . . . . C18 C 0.47963(13) 0.7727(4) 0.4821(3) 0.0428(9) Uani 1 1 d . . . . . C19 C 0.51591(14) 0.8390(4) 0.5100(3) 0.0506(10) Uani 1 1 d . . . . . H19 H 0.513700 0.906037 0.545963 0.061 Uiso 1 1 calc R U . . . C20 C 0.55504(15) 0.8040(5) 0.4837(4) 0.0615(13) Uani 1 1 d . . . . . H20 H 0.579824 0.847417 0.502981 0.074 Uiso 1 1 calc R U . . . C21 C 0.55914(15) 0.7063(5) 0.4293(4) 0.0634(13) Uani 1 1 d . . . . . H21 H 0.586397 0.685888 0.411802 0.076 Uiso 1 1 calc R U . . . C22 C 0.52313(13) 0.6382(4) 0.4003(3) 0.0556(12) Uani 1 1 d . . . . . H22 H 0.525582 0.572069 0.363665 0.067 Uiso 1 1 calc R U . . . C23 C 0.43498(12) 0.5343(3) 0.3415(3) 0.0388(8) Uani 1 1 d . . . . . C24 C 0.39960(17) 0.4776(5) 0.2105(3) 0.0644(14) Uani 1 1 d . . . . . H24 H 0.379445 0.493809 0.162054 0.077 Uiso 1 1 calc R U . . . C25 C 0.41971(19) 0.3705(5) 0.2138(4) 0.0696(16) Uani 1 1 d . . . . . H25 H 0.413834 0.315196 0.167962 0.083 Uiso 1 1 calc R U . . . C26 C 0.44854(17) 0.3449(5) 0.2847(4) 0.0629(14) Uani 1 1 d . . . . . H26 H 0.462949 0.272005 0.288186 0.075 Uiso 1 1 calc R U . . . C27 C 0.45612(14) 0.4279(4) 0.3509(3) 0.0481(10) Uani 1 1 d . . . . . H27 H 0.475226 0.412190 0.401174 0.058 Uiso 1 1 calc R U . . . C28 C 0.500000 -0.0262(8) 0.250000 0.099(4) Uani 1 2 d S T P . . C29 C 0.4638(3) -0.0831(6) 0.2604(5) 0.101(2) Uani 1 1 d . U . . . H29A H 0.468941 -0.167457 0.258914 0.152 Uiso 1 1 calc R U . . . H29B H 0.453564 -0.061880 0.317072 0.152 Uiso 1 1 calc R U . . . H29C H 0.442210 -0.061880 0.212842 0.152 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 0.0560(7) 0.0559(7) 0.0480(6) -0.0124(5) 0.0008(5) -0.0048(5) Cl2 0.0611(7) 0.0556(7) 0.0485(6) -0.0131(5) 0.0103(5) -0.0134(5) Cl3 0.0625(8) 0.1018(11) 0.0735(9) 0.0200(8) 0.0158(6) -0.0330(8) O1 0.0400(16) 0.0496(17) 0.0632(19) 0.0061(15) -0.0085(14) -0.0034(13) O2 0.0402(16) 0.0549(18) 0.0502(17) 0.0033(14) -0.0032(13) 0.0003(13) O3 0.186(8) 0.117(6) 0.260(9) 0.000 0.096(7) 0.000 N1 0.0297(16) 0.0432(17) 0.0395(17) -0.0009(14) 0.0030(13) -0.0040(13) N2 0.0286(16) 0.0454(18) 0.0479(19) -0.0063(15) 0.0075(14) -0.0012(13) N3 0.0429(19) 0.066(2) 0.0409(18) 0.0073(17) 0.0032(15) -0.0046(17) C1 0.0283(18) 0.042(2) 0.0393(19) 0.0004(16) 0.0031(15) -0.0021(15) C2 0.0335(19) 0.045(2) 0.041(2) -0.0004(16) -0.0007(16) -0.0030(16) C3 0.042(2) 0.049(2) 0.057(3) 0.003(2) -0.0008(19) -0.0092(19) C4 0.041(2) 0.060(3) 0.052(2) 0.014(2) 0.0036(19) -0.005(2) C5 0.038(2) 0.066(3) 0.043(2) 0.001(2) 0.0059(17) -0.004(2) C6 0.037(2) 0.045(2) 0.043(2) -0.0004(17) 0.0030(16) -0.0008(16) C7 0.0323(19) 0.039(2) 0.047(2) -0.0031(17) 0.0030(16) -0.0012(16) C8 0.0317(19) 0.045(2) 0.052(2) -0.0017(18) 0.0103(17) -0.0050(16) C9 0.045(2) 0.071(3) 0.043(2) -0.004(2) 0.0088(18) -0.011(2) C10 0.041(2) 0.042(2) 0.0375(19) -0.0047(16) 0.0047(16) -0.0022(17) C11 0.0308(19) 0.041(2) 0.049(2) 0.0012(17) 0.0058(16) -0.0016(16) C12 0.037(2) 0.046(2) 0.059(3) -0.0026(19) 0.0132(18) -0.0010(17) C13 0.048(2) 0.047(2) 0.059(3) -0.004(2) 0.014(2) 0.0078(19) C14 0.044(2) 0.039(2) 0.052(2) -0.0036(18) 0.0040(18) -0.0021(17) C15 0.0351(19) 0.0390(19) 0.041(2) 0.0013(16) 0.0048(15) 0.0004(16) C16 0.0318(19) 0.0386(19) 0.044(2) 0.0041(16) 0.0068(15) 0.0008(15) C17 0.0298(19) 0.050(2) 0.049(2) 0.0001(18) 0.0043(16) -0.0020(16) C18 0.037(2) 0.044(2) 0.047(2) -0.0001(18) 0.0044(17) -0.0043(17) C19 0.041(2) 0.054(3) 0.056(3) 0.000(2) 0.0020(19) -0.0045(19) C20 0.040(2) 0.068(3) 0.076(3) -0.001(3) 0.001(2) -0.013(2) C21 0.031(2) 0.073(3) 0.087(4) -0.012(3) 0.009(2) -0.004(2) C22 0.034(2) 0.063(3) 0.071(3) -0.012(2) 0.011(2) -0.002(2) C23 0.0343(19) 0.046(2) 0.0374(19) -0.0005(16) 0.0097(15) -0.0043(16) C24 0.061(3) 0.094(4) 0.038(2) -0.003(2) 0.005(2) -0.028(3) C25 0.072(3) 0.086(4) 0.055(3) -0.032(3) 0.032(3) -0.038(3) C26 0.059(3) 0.052(3) 0.082(4) -0.018(3) 0.031(3) -0.006(2) C27 0.039(2) 0.048(2) 0.058(3) -0.003(2) 0.0116(19) 0.0016(18) C28 0.193(13) 0.061(5) 0.049(4) 0.000 0.030(6) 0.000 C29 0.123(5) 0.064(3) 0.108(5) 0.011(3) -0.037(4) -0.025(4) 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 '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 C7 N1 C10 113.3(3) . . ? C7 N1 C1 122.9(3) . . ? C10 N1 C1 123.7(3) . . ? C17 N2 C16 107.7(3) . . ? C17 N2 C23 122.5(3) . . ? C16 N2 C23 128.4(3) . . ? C23 N3 C24 116.6(4) . . ? C6 C1 C2 117.8(4) . . ? C6 C1 N1 120.8(3) . . ? C2 C1 N1 121.4(3) . . ? C3 C2 C1 122.2(4) . . ? C3 C2 Cl1 118.6(3) . . ? C1 C2 Cl1 119.2(3) . . ? C2 C3 C4 118.0(4) . . ? C2 C3 H3 121.0 . . ? C4 C3 H3 121.0 . . ? C5 C4 C3 122.5(4) . . ? C5 C4 Cl3 118.4(4) . . ? C3 C4 Cl3 119.0(4) . . ? C4 C5 C6 117.8(4) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? C5 C6 C1 121.7(4) . . ? C5 C6 Cl2 118.5(3) . . ? C1 C6 Cl2 119.8(3) . . ? O1 C7 N1 123.6(4) . . ? O1 C7 C8 128.0(4) . . ? N1 C7 C8 108.4(3) . . ? C7 C8 C11 110.9(3) . . ? C7 C8 C9 104.4(3) . . ? C11 C8 C9 114.2(4) . . ? C7 C8 H8 109.0 . . ? C11 C8 H8 109.0 . . ? C9 C8 H8 109.0 . . ? C10 C9 C8 105.8(3) . . ? C10 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? C10 C9 H9AB 110.6 . . ? C8 C9 H9AB 110.6 . . ? H9A C9 H9AB 108.7 . . ? O2 C10 N1 123.7(4) . . ? O2 C10 C9 128.8(4) . . ? N1 C10 C9 107.5(3) . . ? C12 C11 C16 116.0(4) . . ? C12 C11 C8 118.8(3) . . ? C16 C11 C8 125.2(4) . . ? C11 C12 C13 123.2(4) . . ? C11 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? C14 C13 C12 119.8(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 118.8(4) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? C14 C15 C16 121.0(4) . . ? C14 C15 C18 131.4(4) . . ? C16 C15 C18 107.5(3) . . ? C15 C16 C11 121.0(3) . . ? C15 C16 N2 108.6(3) . . ? C11 C16 N2 130.3(4) . . ? C22 C17 N2 128.8(4) . . ? C22 C17 C18 121.3(4) . . ? N2 C17 C18 109.8(3) . . ? C19 C18 C17 120.3(4) . . ? C19 C18 C15 133.4(4) . . ? C17 C18 C15 106.2(3) . . ? C20 C19 C18 118.3(4) . . ? C20 C19 H19 120.9 . . ? C18 C19 H19 120.9 . . ? C19 C20 C21 122.1(4) . . ? C19 C20 H20 119.0 . . ? C21 C20 H20 119.0 . . ? C20 C21 C22 120.7(4) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C17 C22 C21 117.3(4) . . ? C17 C22 H22 121.4 . . ? C21 C22 H22 121.4 . . ? N3 C23 C27 123.9(4) . . ? N3 C23 N2 116.4(4) . . ? C27 C23 N2 119.7(4) . . ? N3 C24 C25 123.3(5) . . ? N3 C24 H24 118.3 . . ? C25 C24 H24 118.3 . . ? C24 C25 C26 119.0(5) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C25 C26 C27 118.9(5) . . ? C25 C26 H26 120.6 . . ? C27 C26 H26 120.6 . . ? C23 C27 C26 118.2(5) . . ? C23 C27 H27 120.9 . . ? C26 C27 H27 120.9 . . ? O3 C28 C29 119.2(5) . . ? O3 C28 C29 119.2(5) . 2_655 ? C29 C28 C29 121.5(10) . 2_655 ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 C2 1.734(4) . ? Cl2 C6 1.731(4) . ? Cl3 C4 1.741(4) . ? O1 C7 1.209(5) . ? O2 C10 1.205(5) . ? O3 C28 1.217(12) . ? N1 C7 1.394(5) . ? N1 C10 1.403(5) . ? N1 C1 1.427(5) . ? N2 C17 1.400(5) . ? N2 C16 1.412(5) . ? N2 C23 1.417(5) . ? N3 C23 1.322(5) . ? N3 C24 1.348(6) . ? C1 C6 1.393(6) . ? C1 C2 1.395(5) . ? C2 C3 1.367(6) . ? C3 C4 1.390(7) . ? C3 H3 0.9400 . ? C4 C5 1.381(6) . ? C5 C6 1.387(6) . ? C5 H5 0.9400 . ? C7 C8 1.514(6) . ? C8 C11 1.521(6) . ? C8 C9 1.540(6) . ? C8 H8 0.9900 . ? C9 C10 1.506(6) . ? C9 H9A 0.9800 . ? C9 H9AB 0.9800 . ? C11 C12 1.396(6) . ? C11 C16 1.409(5) . ? C12 C13 1.400(6) . ? C12 H12 0.9400 . ? C13 C14 1.380(6) . ? C13 H13 0.9400 . ? C14 C15 1.391(6) . ? C14 H14 0.9400 . ? C15 C16 1.407(5) . ? C15 C18 1.453(6) . ? C17 C22 1.399(6) . ? C17 C18 1.407(6) . ? C18 C19 1.391(6) . ? C19 C20 1.373(7) . ? C19 H19 0.9400 . ? C20 C21 1.392(7) . ? C20 H20 0.9400 . ? C21 C22 1.400(6) . ? C21 H21 0.9400 . ? C22 H22 0.9400 . ? C23 C27 1.376(6) . ? C24 C25 1.365(8) . ? C24 H24 0.9400 . ? C25 C26 1.367(8) . ? C25 H25 0.9400 . ? C26 C27 1.379(7) . ? C26 H26 0.9400 . ? C27 H27 0.9400 . ? C28 C29 1.321(8) . ? C28 C29 1.321(8) 2_655 ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C29 H29C 0.9700 . ?