#------------------------------------------------------------------------------ #$Date: 2024-10-31 03:40:25 +0200 (Thu, 31 Oct 2024) $ #$Revision: 295685 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160194.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_7160194 loop_ _publ_author_name 'Keerthana, Pari' 'Suresh, Sundararajan' 'Nawaz Khan, Fazlur-Rahman' _publ_section_title ; Facile Synthesis of Functionalized Quinolinones in Greener Reaction Medium and Their Photophysical Properties ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01390E _journal_year 2024 _chemical_formula_moiety 'C25 H18 Cl N O3' _chemical_formula_sum 'C25 H18 Cl N O3' _chemical_formula_weight 415.85 _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 2024-08-29 _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _audit_update_record ; 2024-08-29 deposited with the CCDC. 2024-10-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.602(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.624(2) _cell_length_b 5.2910(8) _cell_length_c 23.770(3) _cell_measurement_reflns_used 7401 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 23.35 _cell_measurement_theta_min 2.51 _cell_volume 2040.4(5) _computing_cell_refinement SHELXL _computing_data_collection APEX _computing_data_reduction SAINT _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker D8 Quest' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_unetI/netI 0.0431 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 28713 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.281 _diffrn_reflns_theta_min 1.681 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0880 before and 0.0611 after correction. The Ratio of minimum to maximum transmission is 0.9225. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_description block _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.173 _exptl_crystal_size_mid 0.168 _exptl_crystal_size_min 0.144 _refine_diff_density_max 0.211 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 5037 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.1107 _refine_ls_R_factor_gt 0.0540 _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^)+(0.0700P)^2^+0.7098P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1314 _refine_ls_wR_factor_ref 0.1742 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2796 _reflns_number_total 5037 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01390e2.cif _cod_data_source_block acpb9_070324_0m_a _cod_database_code 7160194 _shelx_shelxl_version_number 2019/3 _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_max 0.970 _shelx_estimated_absorpt_t_min 0.964 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Sof(Cl1B)=1-FVAR(1) Sof(Cl1A)=FVAR(1) 3.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 3.b Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25) 3.c Idealised Me refined as rotating group: C3(H3A,H3B,H3C) ; _shelx_res_file ; TITL ACPB9_070324_0m_a.res in P2(1)/n acpb9_070324_0m_a.res created by SHELXL-2019/3 at 10:33:30 on 29-Aug-2024 REM Old TITL ACPB9_070324_0m in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.243, Rweak 0.011, Alpha 0.027 REM 0.382 for 472 systematic absences, Orientation as input REM Formula found by SHELXT: C25 Cl N C3 CELL 0.71073 16.6237 5.291 23.7703 90 102.602 90 ZERR 4 0.0023 0.0008 0.0033 0 0.005 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 100 72 4 4 12 L.S. 5 PLAN 5 SIZE 0.144 0.168 0.173 TEMP 24.85 CONF BOND LIST 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.070000 0.709800 FVAR 0.79864 0.48773 PART 1 CL1A 3 0.306644 1.080552 0.867982 21.00000 0.08177 0.10103 = 0.07261 -0.01295 0.01105 0.03303 PART 2 CL1B 3 0.301600 1.025110 0.866358 -21.00000 0.09957 0.13692 = 0.08571 0.03356 0.04800 0.06412 PART 0 O1 5 0.401518 0.330741 0.639046 11.00000 0.10970 0.07009 = 0.04879 0.01659 0.00340 -0.02595 O2 5 0.665921 0.062692 0.822241 11.00000 0.08519 0.06633 = 0.08609 0.02640 0.02935 0.01471 O15 5 0.603809 0.385572 0.693862 11.00000 0.08605 0.10260 = 0.03684 0.00468 0.01865 0.02363 N1 4 0.502330 0.645227 0.709907 11.00000 0.05884 0.05705 = 0.02923 0.00619 0.00271 0.00148 C1 1 0.396373 0.540190 0.551151 11.00000 0.05133 0.05026 = 0.03448 0.00430 0.00297 0.00418 C2 1 0.425685 0.726105 0.520931 11.00000 0.09078 0.07978 = 0.04259 0.01347 -0.00677 -0.02966 AFIX 43 H2 2 0.463198 0.844082 0.540278 11.00000 -1.20000 AFIX 0 C3 1 0.747724 0.412573 0.808805 11.00000 0.06196 0.07346 = 0.06943 0.00379 0.00857 0.00482 AFIX 137 H3A 2 0.792840 0.299680 0.822865 11.00000 -1.50000 H3B 2 0.752370 0.557962 0.833466 11.00000 -1.50000 H3C 2 0.749051 0.465183 0.770366 11.00000 -1.50000 AFIX 0 C4 1 0.399334 0.738623 0.461202 11.00000 0.09605 0.09768 = 0.04393 0.02228 0.00455 -0.02233 AFIX 43 H4 2 0.420185 0.863894 0.440917 11.00000 -1.20000 AFIX 0 C5 1 0.344057 0.571879 0.432355 11.00000 0.06662 0.08153 = 0.03458 -0.00210 0.00296 0.00829 AFIX 43 H5 2 0.327110 0.581101 0.392450 11.00000 -1.20000 AFIX 0 C6 1 0.313336 0.389902 0.462289 11.00000 0.08174 0.08159 = 0.04858 -0.00938 0.00006 -0.01689 AFIX 43 H6 2 0.274224 0.276810 0.442739 11.00000 -1.20000 AFIX 0 C7 1 0.339660 0.371557 0.521376 11.00000 0.07387 0.06750 = 0.04475 0.00154 0.00733 -0.01215 AFIX 43 H7 2 0.318930 0.244351 0.541209 11.00000 -1.20000 AFIX 0 C8 1 0.424129 0.509278 0.614520 11.00000 0.05840 0.05033 = 0.03637 0.00736 0.00600 0.00223 C9 1 0.482767 0.700869 0.648117 11.00000 0.06535 0.05952 = 0.03026 0.00912 0.00335 -0.00135 AFIX 23 H9A 2 0.533271 0.702171 0.633981 11.00000 -1.20000 H9B 2 0.458247 0.867709 0.641919 11.00000 -1.20000 AFIX 0 C10 1 0.567024 0.481317 0.728138 11.00000 0.05976 0.06271 = 0.03470 0.00381 0.00815 0.00141 C11 1 0.591063 0.433904 0.790044 11.00000 0.05276 0.04960 = 0.03259 0.00505 0.00644 -0.00043 C12 1 0.548385 0.529471 0.827299 11.00000 0.04817 0.04283 = 0.03029 0.00359 0.00405 -0.00376 C13 1 0.476267 0.681768 0.805801 11.00000 0.04728 0.04564 = 0.03362 0.00336 0.00364 -0.00362 C14 1 0.454165 0.738887 0.746389 11.00000 0.05208 0.04626 = 0.03715 0.00370 0.00191 -0.00270 C16 1 0.577951 0.493840 0.891249 11.00000 0.04698 0.04646 = 0.03066 0.00393 0.00837 0.00300 C17 1 0.550155 0.303083 0.920242 11.00000 0.11291 0.08293 = 0.04557 0.01113 -0.00120 -0.04555 AFIX 43 H17 2 0.511764 0.189011 0.900261 11.00000 -1.20000 AFIX 0 C18 1 0.578425 0.276581 0.979353 11.00000 0.12680 0.09328 = 0.04931 0.02627 0.01251 -0.03787 AFIX 43 H18 2 0.558749 0.144568 0.998418 11.00000 -1.20000 AFIX 0 C19 1 0.633748 0.438506 1.009483 11.00000 0.07069 0.07967 = 0.03112 0.00770 0.00646 0.00468 AFIX 43 H19 2 0.651974 0.420734 1.049147 11.00000 -1.20000 AFIX 0 C20 1 0.662251 0.626731 0.981187 11.00000 0.09658 0.08969 = 0.04013 0.00428 -0.00366 -0.03434 AFIX 43 H20 2 0.700972 0.739161 1.001449 11.00000 -1.20000 AFIX 0 C21 1 0.634571 0.655112 0.922141 11.00000 0.09233 0.07707 = 0.03792 0.01007 0.00191 -0.03470 AFIX 43 H21 2 0.655032 0.786499 0.903345 11.00000 -1.20000 AFIX 0 C22 1 0.428153 0.779256 0.842223 11.00000 0.05257 0.05996 = 0.03911 0.00500 0.00493 0.00151 AFIX 43 H22 2 0.441777 0.741768 0.881378 11.00000 -1.20000 AFIX 0 C23 1 0.361456 0.928715 0.821042 11.00000 0.05367 0.06813 = 0.05481 0.00204 0.01030 0.00843 C24 1 0.339720 0.984739 0.762714 11.00000 0.05777 0.06879 = 0.06282 0.01200 0.00229 0.01458 AFIX 43 H24 2 0.294352 1.087224 0.748610 11.00000 -1.20000 AFIX 0 C25 1 0.384899 0.889516 0.725859 11.00000 0.06348 0.06085 = 0.04408 0.01184 -0.00126 0.00494 AFIX 43 H25 2 0.369337 0.925439 0.686689 11.00000 -1.20000 AFIX 0 C26 1 0.668651 0.280846 0.808367 11.00000 0.06438 0.05736 = 0.03187 0.00623 0.01312 0.00947 HKLF 4 REM ACPB9_070324_0m_a.res in P2(1)/n REM wR2 = 0.1742, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.0540 for 2796 Fo > 4sig(Fo) and 0.1107 for all 5037 data REM 282 parameters refined using 0 restraints END WGHT 0.0700 0.7098 REM Highest difference peak 0.211, deepest hole -0.211, 1-sigma level 0.049 Q1 1 0.5638 0.4984 0.8615 11.00000 0.05 0.21 Q2 1 0.6634 0.8408 1.0060 11.00000 0.05 0.18 Q3 1 0.3209 0.7043 0.5345 11.00000 0.05 0.17 Q4 1 0.2826 0.3370 0.5466 11.00000 0.05 0.17 Q5 1 0.4293 0.8757 0.5393 11.00000 0.05 0.16 ; _shelx_res_checksum 27013 _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 Cl1A Cl 0.3066(5) 1.081(2) 0.8680(3) 0.0860(17) Uani 0.49(5) 1 d . . P A 1 Cl1B Cl 0.3016(7) 1.025(5) 0.8664(4) 0.103(2) Uani 0.51(5) 1 d . . P A 2 O1 O 0.40152(12) 0.3307(3) 0.63905(7) 0.0783(6) Uani 1 1 d . . . . . O2 O 0.66592(12) 0.0627(4) 0.82224(8) 0.0776(6) Uani 1 1 d . . . . . O15 O 0.60381(11) 0.3856(4) 0.69386(6) 0.0744(5) Uani 1 1 d . . . . . N1 N 0.50233(11) 0.6452(3) 0.70991(7) 0.0494(5) Uani 1 1 d . . . . . C1 C 0.39637(13) 0.5402(4) 0.55115(8) 0.0463(5) Uani 1 1 d . . . . . C2 C 0.42568(18) 0.7261(5) 0.52093(10) 0.0743(8) Uani 1 1 d . . . . . H2 H 0.463198 0.844082 0.540278 0.089 Uiso 1 1 calc R U . . . C3 C 0.74772(16) 0.4126(5) 0.80880(12) 0.0692(7) Uani 1 1 d . . . . . H3A H 0.792840 0.299680 0.822865 0.104 Uiso 1 1 calc R U . . . H3B H 0.752370 0.557962 0.833466 0.104 Uiso 1 1 calc R U . . . H3C H 0.749051 0.465183 0.770366 0.104 Uiso 1 1 calc R U . . . C4 C 0.39933(19) 0.7386(6) 0.46120(11) 0.0809(9) Uani 1 1 d . . . . . H4 H 0.420185 0.863894 0.440917 0.097 Uiso 1 1 calc R U . . . C5 C 0.34406(15) 0.5719(5) 0.43235(9) 0.0621(7) Uani 1 1 d . . . . . H5 H 0.327110 0.581101 0.392450 0.075 Uiso 1 1 calc R U . . . C6 C 0.31334(17) 0.3899(6) 0.46229(10) 0.0728(8) Uani 1 1 d . . . . . H6 H 0.274224 0.276810 0.442739 0.087 Uiso 1 1 calc R U . . . C7 C 0.33966(16) 0.3716(5) 0.52138(10) 0.0629(6) Uani 1 1 d . . . . . H7 H 0.318930 0.244351 0.541209 0.075 Uiso 1 1 calc R U . . . C8 C 0.42413(14) 0.5093(4) 0.61452(8) 0.0490(5) Uani 1 1 d . . . . . C9 C 0.48277(15) 0.7009(4) 0.64812(8) 0.0528(6) Uani 1 1 d . . . . . H9A H 0.533271 0.702171 0.633981 0.063 Uiso 1 1 calc R U . . . H9B H 0.458247 0.867709 0.641919 0.063 Uiso 1 1 calc R U . . . C10 C 0.56702(14) 0.4813(5) 0.72814(9) 0.0527(6) Uani 1 1 d . . . . . C11 C 0.59106(13) 0.4339(4) 0.79004(8) 0.0454(5) Uani 1 1 d . . . . . C12 C 0.54838(12) 0.5295(4) 0.82730(8) 0.0411(5) Uani 1 1 d . . . . . C13 C 0.47627(12) 0.6818(4) 0.80580(8) 0.0430(5) Uani 1 1 d . . . . . C14 C 0.45416(13) 0.7389(4) 0.74639(8) 0.0464(5) Uani 1 1 d . . . . . C16 C 0.57795(12) 0.4938(4) 0.89125(8) 0.0414(5) Uani 1 1 d . . . . . C17 C 0.55016(19) 0.3031(6) 0.92024(10) 0.0833(9) Uani 1 1 d . . . . . H17 H 0.511764 0.189011 0.900261 0.100 Uiso 1 1 calc R U . . . C18 C 0.5784(2) 0.2766(6) 0.97935(11) 0.0908(10) Uani 1 1 d . . . . . H18 H 0.558749 0.144568 0.998418 0.109 Uiso 1 1 calc R U . . . C19 C 0.63375(15) 0.4385(5) 1.00948(9) 0.0612(7) Uani 1 1 d . . . . . H19 H 0.651974 0.420734 1.049147 0.073 Uiso 1 1 calc R U . . . C20 C 0.66225(19) 0.6267(6) 0.98119(10) 0.0783(8) Uani 1 1 d . . . . . H20 H 0.700972 0.739161 1.001449 0.094 Uiso 1 1 calc R U . . . C21 C 0.63457(17) 0.6551(5) 0.92214(9) 0.0710(8) Uani 1 1 d . . . . . H21 H 0.655032 0.786499 0.903345 0.085 Uiso 1 1 calc R U . . . C22 C 0.42815(13) 0.7793(4) 0.84222(9) 0.0513(5) Uani 1 1 d . . . . . H22 H 0.441777 0.741768 0.881378 0.062 Uiso 1 1 calc R U . . . C23 C 0.36146(14) 0.9287(5) 0.82104(10) 0.0591(6) Uani 1 1 d . . . . . C24 C 0.33972(16) 0.9847(5) 0.76271(11) 0.0648(7) Uani 1 1 d . . . . . H24 H 0.294352 1.087224 0.748610 0.078 Uiso 1 1 calc R U . . . C25 C 0.38490(15) 0.8895(5) 0.72586(10) 0.0581(6) Uani 1 1 d . . . . . H25 H 0.369337 0.925439 0.686689 0.070 Uiso 1 1 calc R U . . . C26 C 0.66865(14) 0.2808(4) 0.80837(8) 0.0508(6) 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 Cl1A 0.082(2) 0.101(3) 0.073(2) -0.013(4) 0.011(3) 0.033(2) Cl1B 0.100(3) 0.137(6) 0.086(3) 0.034(3) 0.048(3) 0.064(3) O1 0.1097(15) 0.0701(12) 0.0488(10) 0.0166(9) 0.0034(9) -0.0259(11) O2 0.0852(13) 0.0663(12) 0.0861(13) 0.0264(10) 0.0293(10) 0.0147(10) O15 0.0861(12) 0.1026(14) 0.0368(8) 0.0047(9) 0.0187(8) 0.0236(11) N1 0.0588(11) 0.0570(11) 0.0292(8) 0.0062(8) 0.0027(8) 0.0015(9) C1 0.0513(13) 0.0503(13) 0.0345(10) 0.0043(9) 0.0030(9) 0.0042(10) C2 0.0908(19) 0.0798(18) 0.0426(12) 0.0135(12) -0.0068(12) -0.0297(15) C3 0.0620(16) 0.0735(18) 0.0694(16) 0.0038(14) 0.0086(12) 0.0048(14) C4 0.096(2) 0.098(2) 0.0439(13) 0.0223(14) 0.0045(13) -0.0223(18) C5 0.0666(16) 0.0815(18) 0.0346(11) -0.0021(12) 0.0030(11) 0.0083(14) C6 0.0817(18) 0.0816(19) 0.0486(14) -0.0094(13) 0.0001(13) -0.0169(15) C7 0.0739(16) 0.0675(16) 0.0448(12) 0.0015(11) 0.0073(11) -0.0121(13) C8 0.0584(13) 0.0503(13) 0.0364(11) 0.0074(10) 0.0060(10) 0.0022(11) C9 0.0653(14) 0.0595(14) 0.0303(10) 0.0091(10) 0.0034(9) -0.0013(11) C10 0.0598(14) 0.0627(14) 0.0347(11) 0.0038(10) 0.0081(10) 0.0014(12) C11 0.0528(12) 0.0496(12) 0.0326(10) 0.0051(9) 0.0064(9) -0.0004(10) C12 0.0482(12) 0.0428(11) 0.0303(9) 0.0036(8) 0.0040(8) -0.0038(9) C13 0.0473(12) 0.0456(12) 0.0336(10) 0.0034(9) 0.0036(9) -0.0036(9) C14 0.0521(13) 0.0463(12) 0.0372(11) 0.0037(9) 0.0019(9) -0.0027(10) C16 0.0470(12) 0.0465(11) 0.0307(9) 0.0039(9) 0.0084(8) 0.0030(9) C17 0.113(2) 0.083(2) 0.0456(14) 0.0111(13) -0.0012(14) -0.0455(18) C18 0.127(3) 0.093(2) 0.0493(14) 0.0263(15) 0.0125(16) -0.038(2) C19 0.0707(16) 0.0797(18) 0.0311(10) 0.0077(11) 0.0065(10) 0.0047(14) C20 0.097(2) 0.090(2) 0.0401(13) 0.0043(13) -0.0037(13) -0.0343(17) C21 0.0923(19) 0.0771(18) 0.0379(12) 0.0101(12) 0.0019(12) -0.0347(15) C22 0.0526(13) 0.0600(14) 0.0391(11) 0.0050(10) 0.0049(10) 0.0015(11) C23 0.0537(14) 0.0681(16) 0.0548(14) 0.0020(12) 0.0103(11) 0.0084(12) C24 0.0578(15) 0.0688(16) 0.0628(15) 0.0120(13) 0.0023(12) 0.0146(13) C25 0.0635(15) 0.0609(15) 0.0441(12) 0.0118(11) -0.0013(11) 0.0049(12) C26 0.0644(15) 0.0574(15) 0.0319(10) 0.0062(10) 0.0131(9) 0.0095(12) 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 C10 N1 C9 115.48(18) . . ? C10 N1 C14 122.95(16) . . ? C14 N1 C9 121.40(18) . . ? C2 C1 C7 118.6(2) . . ? C2 C1 C8 123.0(2) . . ? C7 C1 C8 118.5(2) . . ? C1 C2 H2 120.0 . . ? C1 C2 C4 120.0(2) . . ? C4 C2 H2 120.0 . . ? H3A C3 H3B 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C26 C3 H3A 109.5 . . ? C26 C3 H3B 109.5 . . ? C26 C3 H3C 109.5 . . ? C2 C4 H4 119.5 . . ? C5 C4 C2 121.0(2) . . ? C5 C4 H4 119.5 . . ? C4 C5 H5 120.4 . . ? C4 C5 C6 119.3(2) . . ? C6 C5 H5 120.4 . . ? C5 C6 H6 119.7 . . ? C5 C6 C7 120.7(2) . . ? C7 C6 H6 119.7 . . ? C1 C7 C6 120.5(2) . . ? C1 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? O1 C8 C1 120.9(2) . . ? O1 C8 C9 120.10(18) . . ? C1 C8 C9 119.00(18) . . ? N1 C9 C8 111.87(18) . . ? N1 C9 H9A 109.2 . . ? N1 C9 H9B 109.2 . . ? C8 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? O15 C10 N1 121.24(19) . . ? O15 C10 C11 122.1(2) . . ? N1 C10 C11 116.68(19) . . ? C10 C11 C26 114.40(18) . . ? C12 C11 C10 122.01(19) . . ? C12 C11 C26 123.54(17) . . ? C11 C12 C13 119.52(17) . . ? C11 C12 C16 120.94(18) . . ? C13 C12 C16 119.42(17) . . ? C14 C13 C12 119.25(19) . . ? C22 C13 C12 122.00(17) . . ? C22 C13 C14 118.74(19) . . ? N1 C14 C13 119.13(18) . . ? N1 C14 C25 121.80(18) . . ? C25 C14 C13 119.1(2) . . ? C17 C16 C12 122.24(19) . . ? C17 C16 C21 117.63(19) . . ? C21 C16 C12 120.13(18) . . ? C16 C17 H17 119.6 . . ? C16 C17 C18 120.7(2) . . ? C18 C17 H17 119.6 . . ? C17 C18 H18 119.5 . . ? C19 C18 C17 121.1(2) . . ? C19 C18 H18 119.5 . . ? C18 C19 H19 120.6 . . ? C18 C19 C20 118.7(2) . . ? C20 C19 H19 120.6 . . ? C19 C20 H20 119.6 . . ? C19 C20 C21 120.7(2) . . ? C21 C20 H20 119.6 . . ? C16 C21 C20 121.1(2) . . ? C16 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C13 C22 H22 119.6 . . ? C23 C22 C13 120.9(2) . . ? C23 C22 H22 119.6 . . ? C22 C23 Cl1A 121.1(3) . . ? C22 C23 Cl1B 118.8(4) . . ? C22 C23 C24 120.4(2) . . ? C24 C23 Cl1A 118.2(4) . . ? C24 C23 Cl1B 120.6(4) . . ? C23 C24 H24 119.9 . . ? C25 C24 C23 120.1(2) . . ? C25 C24 H24 119.9 . . ? C14 C25 H25 119.6 . . ? C24 C25 C14 120.8(2) . . ? C24 C25 H25 119.6 . . ? O2 C26 C3 122.3(2) . . ? O2 C26 C11 120.9(2) . . ? C3 C26 C11 116.8(2) . . ? 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 Cl1A C23 1.779(9) . ? Cl1B C23 1.697(9) . ? O1 C8 1.212(3) . ? O2 C26 1.204(3) . ? O15 C10 1.230(3) . ? N1 C9 1.463(2) . ? N1 C10 1.376(3) . ? N1 C14 1.393(3) . ? C1 C2 1.369(3) . ? C1 C7 1.376(3) . ? C1 C8 1.485(3) . ? C2 H2 0.9300 . ? C2 C4 1.393(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C3 C26 1.486(3) . ? C4 H4 0.9300 . ? C4 C5 1.348(4) . ? C5 H5 0.9300 . ? C5 C6 1.361(4) . ? C6 H6 0.9300 . ? C6 C7 1.380(3) . ? C7 H7 0.9300 . ? C8 C9 1.509(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.460(3) . ? C11 C12 1.348(3) . ? C11 C26 1.505(3) . ? C12 C13 1.442(3) . ? C12 C16 1.504(2) . ? C13 C14 1.412(3) . ? C13 C22 1.399(3) . ? C14 C25 1.398(3) . ? C16 C17 1.359(3) . ? C16 C21 1.361(3) . ? C17 H17 0.9300 . ? C17 C18 1.388(3) . ? C18 H18 0.9300 . ? C18 C19 1.344(4) . ? C19 H19 0.9300 . ? C19 C20 1.345(4) . ? C20 H20 0.9300 . ? C20 C21 1.386(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C22 C23 1.365(3) . ? C23 C24 1.386(3) . ? C24 H24 0.9300 . ? C24 C25 1.368(3) . ? C25 H25 0.9300 . ? 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 Cl1A C23 C24 C25 174.3(5) . . . . ? Cl1B C23 C24 C25 -174.9(10) . . . . ? O1 C8 C9 N1 -2.6(3) . . . . ? O15 C10 C11 C12 -176.9(2) . . . . ? O15 C10 C11 C26 5.7(3) . . . . ? N1 C10 C11 C12 5.0(3) . . . . ? N1 C10 C11 C26 -172.5(2) . . . . ? N1 C14 C25 C24 -178.3(2) . . . . ? C1 C2 C4 C5 1.0(5) . . . . ? C1 C8 C9 N1 178.77(19) . . . . ? C2 C1 C7 C6 0.2(4) . . . . ? C2 C1 C8 O1 -174.2(3) . . . . ? C2 C1 C8 C9 4.4(3) . . . . ? C2 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 -1.5(4) . . . . ? C5 C6 C7 C1 1.2(4) . . . . ? C7 C1 C2 C4 -1.3(4) . . . . ? C7 C1 C8 O1 4.6(3) . . . . ? C7 C1 C8 C9 -176.8(2) . . . . ? C8 C1 C2 C4 177.6(3) . . . . ? C8 C1 C7 C6 -178.7(2) . . . . ? C9 N1 C10 O15 -1.6(3) . . . . ? C9 N1 C10 C11 176.51(19) . . . . ? C9 N1 C14 C13 -179.33(19) . . . . ? C9 N1 C14 C25 0.2(3) . . . . ? C10 N1 C9 C8 86.8(2) . . . . ? C10 N1 C14 C13 5.5(3) . . . . ? C10 N1 C14 C25 -175.0(2) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C10 C11 C12 C16 -175.46(19) . . . . ? C10 C11 C26 O2 -105.6(2) . . . . ? C10 C11 C26 C3 74.8(3) . . . . ? C11 C12 C13 C14 -3.3(3) . . . . ? C11 C12 C13 C22 178.0(2) . . . . ? C11 C12 C16 C17 -95.2(3) . . . . ? C11 C12 C16 C21 84.6(3) . . . . ? C12 C11 C26 O2 77.0(3) . . . . ? C12 C11 C26 C3 -102.6(3) . . . . ? C12 C13 C14 N1 0.4(3) . . . . ? C12 C13 C14 C25 -179.1(2) . . . . ? C12 C13 C22 C23 178.2(2) . . . . ? C12 C16 C17 C18 -179.6(3) . . . . ? C12 C16 C21 C20 179.6(3) . . . . ? C13 C12 C16 C17 88.8(3) . . . . ? C13 C12 C16 C21 -91.4(3) . . . . ? C13 C14 C25 C24 1.2(3) . . . . ? C13 C22 C23 Cl1A -173.2(5) . . . . ? C13 C22 C23 Cl1B 175.9(10) . . . . ? C13 C22 C23 C24 0.6(4) . . . . ? C14 N1 C9 C8 -88.7(2) . . . . ? C14 N1 C10 O15 173.8(2) . . . . ? C14 N1 C10 C11 -8.1(3) . . . . ? C14 C13 C22 C23 -0.6(3) . . . . ? C16 C12 C13 C14 172.77(18) . . . . ? C16 C12 C13 C22 -6.0(3) . . . . ? C16 C17 C18 C19 0.1(5) . . . . ? C17 C16 C21 C20 -0.6(4) . . . . ? C17 C18 C19 C20 -0.7(5) . . . . ? C18 C19 C20 C21 0.6(5) . . . . ? C19 C20 C21 C16 0.0(5) . . . . ? C21 C16 C17 C18 0.5(4) . . . . ? C22 C13 C14 N1 179.20(19) . . . . ? C22 C13 C14 C25 -0.3(3) . . . . ? C22 C23 C24 C25 0.3(4) . . . . ? C23 C24 C25 C14 -1.2(4) . . . . ? C26 C11 C12 C13 177.8(2) . . . . ? C26 C11 C12 C16 1.8(3) . . . . ?