#------------------------------------------------------------------------------ #$Date: 2024-07-05 20:58:23 +0300 (Fri, 05 Jul 2024) $ #$Revision: 293263 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159911.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_7159911 loop_ _publ_author_name 'Siddique, Sidra' 'Hussain, Khalid' 'Shehzadi, Naureen' 'Arshad, Muhammad' 'Arshad, Muhammad Nadeem' 'Iftikhar, Sadaf' 'Saghir, Farhat' 'Shaukat, Ayisha' 'Sarfraz, Muhammad' 'Ahmed, Nisar' _publ_section_title ; Design, synthesis, biological evaluation and molecular docking studies of quinoline-anthranilic acid hybrids as potent anti-inflammatory drugs. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3708 _journal_page_last 3724 _journal_paper_doi 10.1039/d4ob00040d _journal_volume 22 _journal_year 2024 _chemical_formula_moiety 'C18 H15 Cl N2 O2' _chemical_formula_sum 'C18 H15 Cl N2 O2' _chemical_formula_weight 326.77 _chemical_name_common ; 2-Amino-benzoic acid 2-chloro-6-methyl-quinolin-3-ylmethyl ester ; _chemical_name_systematic ; 2-Amino-benzoic acid 2-chloro-6-methyl-quinolin-3-ylmethyl ester ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc2fgxwq _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2024-04-17 deposited with the CCDC. 2024-04-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.077(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5600(8) _cell_length_b 17.5287(18) _cell_length_c 9.6337(10) _cell_measurement_reflns_used 948 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.9 _cell_measurement_theta_min 3.1 _cell_volume 1589.5(3) _computing_cell_refinement 'Bruker APEX3 (Bruker, 2014)' _computing_data_collection 'Bruker APEX3 (Bruker, 2014)' _computing_data_reduction 'Bruker Apex3 SAINT (Bruker, 2014)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 VENTURE dual wavelength Mo/Cu' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0926 _diffrn_reflns_av_unetI/netI 0.0534 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 23986 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 26.388 _diffrn_reflns_theta_min 2.164 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.7056 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 680 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.190 _refine_diff_density_max 0.295 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.071 _refine_ls_extinction_coef 0.013(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 3243 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.1448 _refine_ls_R_factor_gt 0.0727 _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^)+(0.0641P)^2^+3.2851P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1909 _refine_ls_wR_factor_ref 0.2350 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1739 _reflns_number_total 3243 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob00040d2.cif _cod_data_source_block nadeem_ma_sid_ccdc_DRARSHAD _cod_depositor_comments 'Adding full bibliography for 7159911.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7159911 _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_res_file ; TITL mo_MA_SID_PTZ_DrArshad_0m in P2(1)/c shelx.res created by SHELXL-2016/6 at 13:59:30 on 14-Mar-2023 CELL 0.71073 9.5600 17.5287 9.6337 90.000 100.077 90.000 ZERR 4.00 0.0008 0.0018 0.0010 0.000 0.002 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O CL UNIT 72 60 8 8 4 MERG 2 OMIT 2 1 1 OMIT -1 5 2 EQIV $1 -x+1, y+1/2, -z+3/2 HTAB N2 N1_$1 HTAB N2 O1 EQIV $2 -x+1, -y+1, -z+2 HTAB N2 O1_$2 MPLA 10 N1 C1 C2 C3 C4 C5 C6 C7 C8 C9 C18 Cl1 MPLA 6 C12 C13 C14 C15 C16 C17 N2 C11 O1 O2 MPLA 4 O1 C11 O2 C10 MPLA 10 N1 C1 C2 C3 C4 C5 C6 C7 C8 C9 C18 Cl1 FMAP 2 PLAN 20 ACTA 50.00 BOND BOND $H CONF L.S. 20 TEMP 0.00 WGHT 0.064100 3.285100 EXTI 0.012999 FVAR 0.14724 MOLE 1 C1 1 0.813311 0.227954 0.755167 11.00000 0.05133 0.07265 = 0.06821 0.00471 0.02132 -0.00053 C2 1 0.867758 0.302600 0.747123 11.00000 0.05074 0.05785 = 0.06023 0.00427 0.00766 0.00364 C3 1 0.985273 0.308875 0.687534 11.00000 0.05193 0.05478 = 0.07006 0.00375 0.01037 -0.00228 AFIX 43 H3 2 1.025341 0.356695 0.679793 11.00000 -1.20000 AFIX 0 C4 1 1.048337 0.243815 0.636716 11.00000 0.04550 0.05332 = 0.06218 0.00568 0.01383 0.00171 C5 1 0.983142 0.173118 0.648149 11.00000 0.04448 0.05398 = 0.05625 0.00593 0.00643 0.00014 C6 1 1.040961 0.107584 0.597337 11.00000 0.06532 0.05431 = 0.06965 0.00597 0.00525 0.00341 AFIX 43 H6 2 0.997901 0.060475 0.604065 11.00000 -1.20000 AFIX 0 C7 1 1.159216 0.112450 0.538469 11.00000 0.07095 0.06521 = 0.07271 -0.00527 0.00794 0.01337 AFIX 43 H7 2 1.195333 0.068388 0.504165 11.00000 -1.20000 AFIX 0 C8 1 1.228923 0.182144 0.527722 11.00000 0.05307 0.07912 = 0.07487 -0.00351 0.01458 0.01171 C9 1 1.172352 0.246610 0.576063 11.00000 0.05851 0.06003 = 0.08276 0.00140 0.02258 -0.00509 AFIX 43 H9 2 1.216659 0.293311 0.568765 11.00000 -1.20000 AFIX 0 C10 1 0.797358 0.370082 0.800957 11.00000 0.05004 0.07640 = 0.06604 -0.00684 0.00130 0.00912 AFIX 23 H10A 2 0.778445 0.359951 0.894919 11.00000 -1.20000 H10B 2 0.858171 0.414614 0.804997 11.00000 -1.20000 AFIX 0 C11 1 0.572400 0.429586 0.752795 11.00000 0.04920 0.04713 = 0.06193 -0.00343 0.01443 0.00138 C12 1 0.442693 0.439642 0.648831 11.00000 0.04955 0.05048 = 0.05161 -0.00197 0.01443 0.00055 C13 1 0.428793 0.405323 0.516332 11.00000 0.05921 0.06011 = 0.05306 -0.00233 0.01627 0.00307 AFIX 43 H13 2 0.502011 0.374516 0.496494 11.00000 -1.20000 AFIX 0 C14 1 0.311114 0.415505 0.414777 11.00000 0.06812 0.07409 = 0.06369 -0.00589 0.00729 -0.00073 AFIX 43 H14 2 0.303825 0.392163 0.327112 11.00000 -1.20000 AFIX 0 C15 1 0.204100 0.461106 0.445789 11.00000 0.06429 0.08141 = 0.07069 0.00920 0.00251 0.00197 AFIX 43 H15 2 0.123162 0.468363 0.377964 11.00000 -1.20000 AFIX 0 C16 1 0.213384 0.496147 0.573811 11.00000 0.05548 0.07246 = 0.08363 0.00347 0.01316 0.01600 AFIX 43 H16 2 0.139150 0.527130 0.590596 11.00000 -1.20000 AFIX 0 C17 1 0.331264 0.486553 0.679588 11.00000 0.05709 0.05561 = 0.05700 0.00133 0.01776 0.00368 C18 1 1.362650 0.185788 0.463925 11.00000 0.07855 0.10413 = 0.13562 -0.01146 0.05527 0.01240 AFIX 33 H18A 2 1.386484 0.135521 0.436084 11.00000 -1.50000 H18B 2 1.347045 0.218596 0.382894 11.00000 -1.50000 H18C 2 1.439233 0.205557 0.532336 11.00000 -1.50000 AFIX 0 N1 3 0.865223 0.165539 0.709545 11.00000 0.05871 0.05737 = 0.07567 0.00931 0.01994 -0.00768 N2 3 0.335351 0.521132 0.805921 11.00000 0.08726 0.09242 = 0.07131 -0.01683 0.01685 0.03136 AFIX 93 H2A 2 0.265217 0.548914 0.820545 11.00000 -1.20000 H2B 2 0.408082 0.515313 0.871534 11.00000 -1.20000 AFIX 0 O1 4 0.598223 0.457755 0.869363 11.00000 0.07291 0.08177 = 0.05685 -0.01926 0.00778 0.00772 O2 4 0.666139 0.383012 0.704479 11.00000 0.05492 0.07665 = 0.05736 -0.00934 0.00630 0.01576 CL1 5 0.665654 0.215908 0.837362 11.00000 0.08667 0.10336 = 0.13375 0.00986 0.06867 -0.00618 HKLF 4 REM mo_MA_SID_PTZ_DrArshad_0m in P2(1)/c REM R1 = 0.0727 for 1739 Fo > 4sig(Fo) and 0.1448 for all 3243 data REM 209 parameters refined using 0 restraints END WGHT 0.0642 3.2823 REM Highest difference peak 0.295, deepest hole -0.285, 1-sigma level 0.071 Q1 1 1.3612 0.2599 0.4448 11.00000 0.05 0.30 Q2 1 1.3909 0.2527 0.4676 11.00000 0.05 0.29 Q3 1 0.6828 0.3107 0.8237 11.00000 0.05 0.26 Q4 1 0.8367 0.3989 0.6695 11.00000 0.05 0.26 Q5 1 0.6451 0.2931 0.8320 11.00000 0.05 0.25 Q6 1 0.5281 0.1659 0.8185 11.00000 0.05 0.24 Q7 1 0.5993 0.2090 0.7558 11.00000 0.05 0.23 Q8 1 0.8434 0.2749 0.7306 11.00000 0.05 0.22 Q9 1 0.5353 0.2721 0.8495 11.00000 0.05 0.21 Q10 1 0.5372 0.3933 0.8956 11.00000 0.05 0.21 Q11 1 1.3537 0.1566 0.3431 11.00000 0.05 0.21 Q12 1 1.1529 0.3120 0.5344 11.00000 0.05 0.21 Q13 1 0.5002 0.4723 0.9278 11.00000 0.05 0.20 Q14 1 0.9065 0.3750 0.6016 11.00000 0.05 0.20 Q15 1 1.0410 0.2644 0.5619 11.00000 0.05 0.20 Q16 1 0.1696 0.5251 0.6957 11.00000 0.05 0.20 Q17 1 0.6876 0.2626 0.7221 11.00000 0.05 0.20 Q18 1 1.4528 0.2236 0.3470 11.00000 0.05 0.19 Q19 1 0.5075 0.4220 0.3349 11.00000 0.05 0.18 Q20 1 0.3241 0.3697 0.5419 11.00000 0.05 0.18 ; _shelx_res_checksum 73904 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 0.8133(5) 0.2280(3) 0.7552(6) 0.0628(14) Uani 1 1 d . . . . . C2 C 0.8678(5) 0.3026(3) 0.7471(5) 0.0565(12) Uani 1 1 d . . . . . C3 C 0.9853(5) 0.3089(3) 0.6875(5) 0.0590(13) Uani 1 1 d . . . . . H3 H 1.025341 0.356695 0.679793 0.071 Uiso 1 1 calc R U . . . C4 C 1.0483(5) 0.2438(3) 0.6367(5) 0.0531(12) Uani 1 1 d . . . . . C5 C 0.9831(5) 0.1731(3) 0.6481(5) 0.0519(11) Uani 1 1 d . . . . . C6 C 1.0410(6) 0.1076(3) 0.5973(6) 0.0639(14) Uani 1 1 d . . . . . H6 H 0.997901 0.060475 0.604065 0.077 Uiso 1 1 calc R U . . . C7 C 1.1592(6) 0.1125(3) 0.5385(6) 0.0702(15) Uani 1 1 d . . . . . H7 H 1.195333 0.068388 0.504165 0.084 Uiso 1 1 calc R U . . . C8 C 1.2289(5) 0.1821(3) 0.5277(6) 0.0686(15) Uani 1 1 d . . . . . C9 C 1.1724(5) 0.2466(3) 0.5761(6) 0.0659(14) Uani 1 1 d . . . . . H9 H 1.216659 0.293311 0.568765 0.079 Uiso 1 1 calc R U . . . C10 C 0.7974(5) 0.3701(3) 0.8010(6) 0.0652(14) Uani 1 1 d . . . . . H10A H 0.778445 0.359951 0.894919 0.078 Uiso 1 1 calc R U . . . H10B H 0.858171 0.414614 0.804997 0.078 Uiso 1 1 calc R U . . . C11 C 0.5724(5) 0.4296(3) 0.7528(5) 0.0522(12) Uani 1 1 d . . . . . C12 C 0.4427(5) 0.4396(3) 0.6488(5) 0.0499(11) Uani 1 1 d . . . . . C13 C 0.4288(5) 0.4053(3) 0.5163(5) 0.0567(12) Uani 1 1 d . . . . . H13 H 0.502011 0.374516 0.496494 0.068 Uiso 1 1 calc R U . . . C14 C 0.3111(6) 0.4155(3) 0.4148(6) 0.0691(15) Uani 1 1 d . . . . . H14 H 0.303825 0.392163 0.327112 0.083 Uiso 1 1 calc R U . . . C15 C 0.2041(6) 0.4611(3) 0.4458(6) 0.0732(16) Uani 1 1 d . . . . . H15 H 0.123162 0.468363 0.377964 0.088 Uiso 1 1 calc R U . . . C16 C 0.2134(6) 0.4961(3) 0.5738(6) 0.0704(15) Uani 1 1 d . . . . . H16 H 0.139150 0.527130 0.590596 0.084 Uiso 1 1 calc R U . . . C17 C 0.3313(5) 0.4866(3) 0.6796(5) 0.0556(12) Uani 1 1 d . . . . . C18 C 1.3626(7) 0.1858(4) 0.4639(8) 0.102(2) Uani 1 1 d . . . . . H18A H 1.386484 0.135521 0.436084 0.153 Uiso 1 1 calc R U . . . H18B H 1.347045 0.218596 0.382894 0.153 Uiso 1 1 calc R U . . . H18C H 1.439233 0.205557 0.532336 0.153 Uiso 1 1 calc R U . . . N1 N 0.8652(4) 0.1655(2) 0.7095(5) 0.0629(11) Uani 1 1 d . . . . . N2 N 0.3354(5) 0.5211(3) 0.8059(5) 0.0833(15) Uani 1 1 d . . . . . H2A H 0.265217 0.548914 0.820545 0.100 Uiso 1 1 calc R U . . . H2B H 0.408082 0.515313 0.871534 0.100 Uiso 1 1 calc R U . . . O1 O 0.5982(4) 0.4578(2) 0.8694(4) 0.0709(11) Uani 1 1 d . . . . . O2 O 0.6661(3) 0.3830(2) 0.7045(4) 0.0634(10) Uani 1 1 d . . . . . Cl1 Cl 0.66565(18) 0.21591(10) 0.8374(2) 0.1020(7) 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 C1 0.051(3) 0.073(4) 0.068(3) 0.005(3) 0.021(3) -0.001(3) C2 0.051(3) 0.058(3) 0.060(3) 0.004(2) 0.008(2) 0.004(2) C3 0.052(3) 0.055(3) 0.070(3) 0.004(3) 0.010(2) -0.002(2) C4 0.046(2) 0.053(3) 0.062(3) 0.006(2) 0.014(2) 0.002(2) C5 0.044(2) 0.054(3) 0.056(3) 0.006(2) 0.006(2) 0.000(2) C6 0.065(3) 0.054(3) 0.070(4) 0.006(3) 0.005(3) 0.003(3) C7 0.071(4) 0.065(4) 0.073(4) -0.005(3) 0.008(3) 0.013(3) C8 0.053(3) 0.079(4) 0.075(4) -0.004(3) 0.015(3) 0.012(3) C9 0.059(3) 0.060(3) 0.083(4) 0.001(3) 0.023(3) -0.005(2) C10 0.050(3) 0.076(4) 0.066(3) -0.007(3) 0.001(2) 0.009(3) C11 0.049(3) 0.047(3) 0.062(3) -0.003(2) 0.014(2) 0.001(2) C12 0.050(3) 0.050(3) 0.052(3) -0.002(2) 0.014(2) 0.001(2) C13 0.059(3) 0.060(3) 0.053(3) -0.002(2) 0.016(2) 0.003(2) C14 0.068(3) 0.074(4) 0.064(3) -0.006(3) 0.007(3) -0.001(3) C15 0.064(3) 0.081(4) 0.071(4) 0.009(3) 0.003(3) 0.002(3) C16 0.055(3) 0.072(4) 0.084(4) 0.003(3) 0.013(3) 0.016(3) C17 0.057(3) 0.056(3) 0.057(3) 0.001(2) 0.018(2) 0.004(2) C18 0.079(4) 0.104(5) 0.136(6) -0.011(5) 0.055(4) 0.012(4) N1 0.059(2) 0.057(3) 0.076(3) 0.009(2) 0.020(2) -0.008(2) N2 0.087(3) 0.092(4) 0.071(3) -0.017(3) 0.017(3) 0.031(3) O1 0.073(2) 0.082(3) 0.057(2) -0.0193(19) 0.0078(18) 0.0077(19) O2 0.055(2) 0.077(2) 0.057(2) -0.0093(17) 0.0063(16) 0.0158(17) Cl1 0.0867(11) 0.1034(13) 0.1337(16) 0.0099(11) 0.0687(11) -0.0062(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _citation_id _citation_doi _citation_year 1 10.1039/D4OB00040D 2024 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 N1 C1 C2 126.1(4) . . ? N1 C1 Cl1 115.8(4) . . ? C2 C1 Cl1 118.1(4) . . ? C3 C2 C1 116.1(5) . . ? C3 C2 C10 122.7(5) . . ? C1 C2 C10 121.3(4) . . ? C2 C3 C4 121.1(5) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C9 118.8(4) . . ? C5 C4 C3 117.6(4) . . ? C9 C4 C3 123.7(5) . . ? N1 C5 C6 118.5(4) . . ? N1 C5 C4 122.1(4) . . ? C6 C5 C4 119.4(4) . . ? C7 C6 C5 120.3(5) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 121.9(5) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C9 C8 C7 118.2(5) . . ? C9 C8 C18 121.0(5) . . ? C7 C8 C18 120.8(5) . . ? C8 C9 C4 121.5(5) . . ? C8 C9 H9 119.2 . . ? C4 C9 H9 119.2 . . ? O2 C10 C2 107.1(4) . . ? O2 C10 H10A 110.3 . . ? C2 C10 H10A 110.3 . . ? O2 C10 H10B 110.3 . . ? C2 C10 H10B 110.3 . . ? H10A C10 H10B 108.6 . . ? O1 C11 O2 121.6(4) . . ? O1 C11 C12 126.6(4) . . ? O2 C11 C12 111.7(4) . . ? C13 C12 C17 119.1(4) . . ? C13 C12 C11 120.5(4) . . ? C17 C12 C11 120.3(4) . . ? C14 C13 C12 122.2(5) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 118.2(5) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C16 C15 C14 121.7(5) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 121.5(5) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? N2 C17 C16 119.8(5) . . ? N2 C17 C12 122.9(5) . . ? C16 C17 C12 117.3(5) . . ? C8 C18 H18A 109.5 . . ? C8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C1 N1 C5 117.0(4) . . ? C17 N2 H2A 120.0 . . ? C17 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C11 O2 C10 115.3(4) . . ? 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 C1 N1 1.309(6) . ? C1 C2 1.415(7) . ? C1 Cl1 1.748(5) . ? C2 C3 1.353(7) . ? C2 C10 1.498(7) . ? C3 C4 1.417(7) . ? C3 H3 0.9300 . ? C4 C5 1.400(6) . ? C4 C9 1.411(6) . ? C5 N1 1.368(6) . ? C5 C6 1.400(7) . ? C6 C7 1.353(7) . ? C6 H6 0.9300 . ? C7 C8 1.404(8) . ? C7 H7 0.9300 . ? C8 C9 1.369(7) . ? C8 C18 1.514(7) . ? C9 H9 0.9300 . ? C10 O2 1.443(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.212(5) . ? C11 O2 1.354(5) . ? C11 C12 1.462(6) . ? C12 C13 1.396(6) . ? C12 C17 1.417(6) . ? C13 C14 1.367(7) . ? C13 H13 0.9300 . ? C14 C15 1.372(8) . ? C14 H14 0.9300 . ? C15 C16 1.367(8) . ? C15 H15 0.9300 . ? C16 C17 1.391(7) . ? C16 H16 0.9300 . ? C17 N2 1.354(6) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A N1 0.86 2.39 3.163(6) 150.6 2_656 N2 H2B O1 0.86 2.08 2.718(6) 130.2 . N2 H2B O1 0.86 2.55 3.103(6) 122.9 3_667 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 N1 C1 C2 C3 -0.6(8) . . . . ? Cl1 C1 C2 C3 177.6(4) . . . . ? N1 C1 C2 C10 178.9(5) . . . . ? Cl1 C1 C2 C10 -2.9(7) . . . . ? C1 C2 C3 C4 0.1(7) . . . . ? C10 C2 C3 C4 -179.5(5) . . . . ? C2 C3 C4 C5 1.1(7) . . . . ? C2 C3 C4 C9 -178.8(5) . . . . ? C9 C4 C5 N1 178.0(5) . . . . ? C3 C4 C5 N1 -1.9(7) . . . . ? C9 C4 C5 C6 -1.0(7) . . . . ? C3 C4 C5 C6 179.1(5) . . . . ? N1 C5 C6 C7 -178.7(5) . . . . ? C4 C5 C6 C7 0.4(8) . . . . ? C5 C6 C7 C8 0.9(8) . . . . ? C6 C7 C8 C9 -1.4(8) . . . . ? C6 C7 C8 C18 178.8(6) . . . . ? C7 C8 C9 C4 0.7(8) . . . . ? C18 C8 C9 C4 -179.5(6) . . . . ? C5 C4 C9 C8 0.5(8) . . . . ? C3 C4 C9 C8 -179.6(5) . . . . ? C3 C2 C10 O2 108.0(5) . . . . ? C1 C2 C10 O2 -71.5(6) . . . . ? O1 C11 C12 C13 178.1(5) . . . . ? O2 C11 C12 C13 -2.1(6) . . . . ? O1 C11 C12 C17 0.3(8) . . . . ? O2 C11 C12 C17 -180.0(4) . . . . ? C17 C12 C13 C14 0.1(7) . . . . ? C11 C12 C13 C14 -177.8(5) . . . . ? C12 C13 C14 C15 0.0(8) . . . . ? C13 C14 C15 C16 0.3(9) . . . . ? C14 C15 C16 C17 -0.7(9) . . . . ? C15 C16 C17 N2 -178.8(5) . . . . ? C15 C16 C17 C12 0.8(8) . . . . ? C13 C12 C17 N2 179.1(5) . . . . ? C11 C12 C17 N2 -3.0(7) . . . . ? C13 C12 C17 C16 -0.5(7) . . . . ? C11 C12 C17 C16 177.4(5) . . . . ? C2 C1 N1 C5 -0.1(8) . . . . ? Cl1 C1 N1 C5 -178.3(4) . . . . ? C6 C5 N1 C1 -179.6(5) . . . . ? C4 C5 N1 C1 1.4(7) . . . . ? O1 C11 O2 C10 -0.3(7) . . . . ? C12 C11 O2 C10 180.0(4) . . . . ? C2 C10 O2 C11 164.9(4) . . . . ?