#------------------------------------------------------------------------------ #$Date: 2020-10-06 13:58:27 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257921 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157504.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_7157504 loop_ _publ_author_name 'Hu, Fang-Peng' 'Cui, Xin-Feng' 'Lu, Guo-Qiang' 'Huang, Guo-Sheng' _publ_section_title ; Base-promoted Lewis acid catalyzed synthesis of quinazoline derivatives. ; _journal_issue 23 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4376 _journal_page_last 4380 _journal_paper_doi 10.1039/d0ob00225a _journal_volume 18 _journal_year 2020 _chemical_formula_sum 'C16 H13 Cl N2 O' _chemical_formula_weight 284.73 _space_group_crystal_system orthorhombic _space_group_IT_number 56 _space_group_name_Hall '-P 2ab 2ac' _space_group_name_H-M_alt 'P c c n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/ccdc.csd.cc24045h _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-11-18 deposited with the CCDC. 2020-05-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.9470(18) _cell_length_b 16.934(3) _cell_length_c 18.608(4) _cell_measurement_reflns_used 2962 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 22.71 _cell_measurement_theta_min 2.50 _cell_volume 2819.3(10) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART APEX II' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 'fine-focus sealed tube' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX II area detector' _diffrn_measurement_method '\w scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_unetI/netI 0.0298 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 13695 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.338 _diffrn_reflns_theta_min 2.189 _exptl_absorpt_coefficient_mu 0.267 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.342 _exptl_crystal_description block _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_transmission_factor_max 0.7452 _exptl_transmission_factor_min 0.5613 _refine_diff_density_max 0.558 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2588 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.003 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0614 _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^)+(0.1000P)^2^+1.8525P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1758 _refine_ls_wR_factor_ref 0.2017 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1764 _reflns_number_total 2588 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00225a2.cif _cod_data_source_block 1_a _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7157504.cif. Adding full bibliography for 7157504.cif. ; _cod_original_cell_volume 2819.4(10) _cod_database_code 7157504 _shelx_shelxl_version_number 2014/7 _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 0.924 _shelx_estimated_absorpt_t_max 0.948 _shelx_res_file ; 1_a.res created by SHELXL-2014/7 TITL 1_a.res in Pccn CELL 0.71073 8.9470 16.9345 18.6080 90.000 90.000 90.000 ZERR 8.000 0.0018 0.0034 0.0037 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, 1/2-Y, Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, -Y, 1/2-Z SFAC C H N O Cl UNIT 128 104 16 8 8 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.30 0.20 0.20 CONF TEMP 23.000 WGHT 0.100000 1.852520 FVAR 0.42227 C1 1 0.526922 0.351933 0.571766 11.00000 0.10942 0.09688 = 0.09041 -0.01926 0.03706 -0.02974 AFIX 43 H1 2 0.600105 0.331839 0.602185 11.00000 -1.20000 AFIX 0 C2 1 0.485283 0.310807 0.509743 11.00000 0.16248 0.10855 = 0.09847 -0.02723 0.06655 -0.05207 AFIX 43 H2 2 0.529987 0.262748 0.498656 11.00000 -1.20000 AFIX 0 C3 1 0.375064 0.342799 0.464217 11.00000 0.18507 0.14190 = 0.06851 -0.02837 0.03806 -0.09423 AFIX 43 H3 2 0.348714 0.315526 0.422728 11.00000 -1.20000 AFIX 0 C4 1 0.306003 0.412509 0.479216 11.00000 0.15085 0.14022 = 0.05660 -0.00450 0.01281 -0.07890 AFIX 43 H4 2 0.233515 0.432380 0.448295 11.00000 -1.20000 AFIX 0 C5 1 0.344922 0.454146 0.541613 11.00000 0.08954 0.11400 = 0.04922 0.00417 0.00777 -0.05442 C6 1 0.456562 0.424019 0.587412 11.00000 0.07810 0.08816 = 0.06034 -0.00493 0.02168 -0.03200 C7 1 0.269902 0.526540 0.559383 11.00000 0.07715 0.11162 = 0.05493 0.02072 -0.00677 -0.03416 C8 1 0.426950 0.527324 0.666038 11.00000 0.04923 0.06727 = 0.05224 0.01556 -0.00041 -0.01121 C9 1 0.472390 0.568427 0.733144 11.00000 0.04973 0.05422 = 0.05542 0.01168 -0.00581 0.00348 C10 1 0.381452 0.569972 0.793589 11.00000 0.06204 0.07336 = 0.06325 0.01111 0.00225 0.00343 AFIX 43 H10 2 0.285984 0.548341 0.791781 11.00000 -1.20000 AFIX 0 C11 1 0.433343 0.603829 0.856592 11.00000 0.09219 0.08948 = 0.05611 0.00565 0.00165 0.02011 AFIX 43 H11 2 0.373369 0.603893 0.897413 11.00000 -1.20000 AFIX 0 C12 1 0.573999 0.637524 0.858990 11.00000 0.09050 0.07999 = 0.06882 -0.00489 -0.02933 0.02165 AFIX 43 H12 2 0.607443 0.661247 0.901099 11.00000 -1.20000 AFIX 0 C13 1 0.664007 0.636089 0.799717 11.00000 0.06093 0.08091 = 0.08369 0.00260 -0.02402 0.00404 AFIX 43 H13 2 0.758741 0.658599 0.801567 11.00000 -1.20000 AFIX 0 C14 1 0.614544 0.601376 0.737356 11.00000 0.04966 0.07357 = 0.06532 0.00977 -0.00781 0.00058 AFIX 43 H14 2 0.676961 0.599889 0.697414 11.00000 -1.20000 AFIX 0 C15 1 0.237072 0.633608 0.644065 11.00000 0.05915 0.07336 = 0.08121 0.03667 -0.01029 -0.00951 AFIX 23 H15A 2 0.230109 0.667313 0.602050 11.00000 -1.20000 H15B 2 0.294563 0.661322 0.680356 11.00000 -1.20000 AFIX 0 C16 1 0.080825 0.616619 0.672720 11.00000 0.06245 0.07823 = 0.11224 0.04137 -0.00073 -0.00690 AFIX 23 H16A 2 0.087762 0.584972 0.716041 11.00000 -1.20000 H16B 2 0.024524 0.586942 0.637293 11.00000 -1.20000 AFIX 0 CL1 5 -0.012262 0.705950 0.691853 11.00000 0.07615 0.09424 = 0.23644 0.06780 0.03009 0.01705 N1 3 0.313357 0.559967 0.624882 11.00000 0.05748 0.08008 = 0.05324 0.01946 -0.00644 -0.01601 N2 3 0.498207 0.463173 0.649921 11.00000 0.06124 0.07129 = 0.06338 -0.00087 0.00487 -0.00985 O1 4 0.174667 0.558350 0.522298 11.00000 0.10504 0.16779 = 0.07556 0.04035 -0.03774 -0.03346 HKLF 4 REM 1_a.res in Pccn REM R1 = 0.0614 for 1764 Fo > 4sig(Fo) and 0.0881 for all 2588 data REM 181 parameters refined using 0 restraints END WGHT 0.0760 1.8727 REM Highest difference peak 0.558, deepest hole -0.684, 1-sigma level 0.042 Q1 1 -0.0020 0.6824 0.6419 11.00000 0.05 0.56 Q2 1 -0.0305 0.7178 0.7019 11.00000 0.05 0.31 Q3 1 0.0556 0.7146 0.7186 11.00000 0.05 0.26 Q4 1 0.2139 0.5036 0.5014 11.00000 0.05 0.14 Q5 1 0.1326 0.5617 0.5443 11.00000 0.05 0.14 Q6 1 0.3813 0.4222 0.5506 11.00000 0.05 0.13 Q7 1 0.5595 0.2730 0.5362 11.00000 0.05 0.12 Q8 1 0.5017 0.3825 0.5784 11.00000 0.05 0.12 Q9 1 0.4802 0.3352 0.5477 11.00000 0.05 0.12 Q10 1 0.3769 0.4793 0.5496 11.00000 0.05 0.11 Q11 1 0.3426 0.4571 0.5071 11.00000 0.05 0.11 Q12 1 0.4383 0.2840 0.4684 11.00000 0.05 0.10 Q13 1 0.5816 0.4597 0.6720 11.00000 0.05 0.10 Q14 1 0.4136 0.2757 0.4346 11.00000 0.05 0.10 Q15 1 0.0909 0.5809 0.6305 11.00000 0.05 0.09 Q16 1 0.5085 0.5976 0.7302 11.00000 0.05 0.09 Q17 1 0.3392 0.3608 0.4935 11.00000 0.05 0.09 Q18 1 0.5081 0.5680 0.7432 11.00000 0.05 0.09 Q19 1 0.1168 0.7085 0.6682 11.00000 0.05 0.09 Q20 1 0.3570 0.6643 0.8929 11.00000 0.05 0.08 ; _shelx_res_checksum 71505 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, 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 0.5269(5) 0.3519(3) 0.5718(2) 0.0989(13) Uani 1 1 d . . . . . H1 H 0.6001 0.3318 0.6022 0.119 Uiso 1 1 calc R U . . . C2 C 0.4853(7) 0.3108(3) 0.5097(3) 0.123(2) Uani 1 1 d . . . . . H2 H 0.5300 0.2627 0.4987 0.148 Uiso 1 1 calc R U . . . C3 C 0.3751(8) 0.3428(4) 0.4642(3) 0.132(2) Uani 1 1 d . . . . . H3 H 0.3487 0.3155 0.4227 0.158 Uiso 1 1 calc R U . . . C4 C 0.3060(6) 0.4125(4) 0.4792(2) 0.1159(19) Uani 1 1 d . . . . . H4 H 0.2335 0.4324 0.4483 0.139 Uiso 1 1 calc R U . . . C5 C 0.3449(5) 0.4541(3) 0.54161(17) 0.0843(12) Uani 1 1 d . . . . . C6 C 0.4566(4) 0.4240(2) 0.58741(18) 0.0755(10) Uani 1 1 d . . . . . C7 C 0.2699(4) 0.5265(3) 0.55938(18) 0.0812(11) Uani 1 1 d . . . . . C8 C 0.4270(3) 0.52732(19) 0.66604(15) 0.0562(7) Uani 1 1 d . . . . . C9 C 0.4724(3) 0.56843(17) 0.73314(15) 0.0531(7) Uani 1 1 d . . . . . C10 C 0.3815(4) 0.5700(2) 0.79359(16) 0.0662(8) Uani 1 1 d . . . . . H10 H 0.2860 0.5483 0.7918 0.079 Uiso 1 1 calc R U . . . C11 C 0.4333(5) 0.6038(2) 0.85659(18) 0.0793(10) Uani 1 1 d . . . . . H11 H 0.3734 0.6039 0.8974 0.095 Uiso 1 1 calc R U . . . C12 C 0.5740(5) 0.6375(2) 0.8590(2) 0.0798(10) Uani 1 1 d . . . . . H12 H 0.6074 0.6612 0.9011 0.096 Uiso 1 1 calc R U . . . C13 C 0.6640(4) 0.6361(2) 0.79972(19) 0.0752(10) Uani 1 1 d . . . . . H13 H 0.7587 0.6586 0.8016 0.090 Uiso 1 1 calc R U . . . C14 C 0.6145(3) 0.60138(19) 0.73736(17) 0.0628(8) Uani 1 1 d . . . . . H14 H 0.6770 0.5999 0.6974 0.075 Uiso 1 1 calc R U . . . C15 C 0.2371(4) 0.6336(2) 0.64406(18) 0.0712(9) Uani 1 1 d . . . . . H15A H 0.2301 0.6673 0.6021 0.085 Uiso 1 1 calc R U . . . H15B H 0.2946 0.6613 0.6804 0.085 Uiso 1 1 calc R U . . . C16 C 0.0808(4) 0.6166(2) 0.6727(2) 0.0843(11) Uani 1 1 d . . . . . H16A H 0.0878 0.5850 0.7160 0.101 Uiso 1 1 calc R U . . . H16B H 0.0245 0.5869 0.6373 0.101 Uiso 1 1 calc R U . . . Cl1 Cl -0.01226(12) 0.70595(7) 0.69185(10) 0.1356(7) Uani 1 1 d . . . . . N1 N 0.3134(3) 0.55997(16) 0.62488(13) 0.0636(7) Uani 1 1 d . . . . . N2 N 0.4982(3) 0.46317(17) 0.64992(14) 0.0653(7) Uani 1 1 d . . . . . O1 O 0.1747(3) 0.5584(2) 0.52230(14) 0.1161(11) 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 0.109(3) 0.097(3) 0.090(3) -0.019(2) 0.037(2) -0.030(3) C2 0.162(5) 0.109(4) 0.098(4) -0.027(3) 0.067(4) -0.052(4) C3 0.185(6) 0.142(5) 0.069(3) -0.028(3) 0.038(3) -0.094(5) C4 0.151(4) 0.140(4) 0.057(2) -0.005(3) 0.013(2) -0.079(4) C5 0.090(3) 0.114(3) 0.0492(18) 0.004(2) 0.0078(18) -0.054(2) C6 0.078(2) 0.088(3) 0.060(2) -0.0049(18) 0.0217(17) -0.0320(19) C7 0.077(2) 0.112(3) 0.0549(19) 0.021(2) -0.0068(18) -0.034(2) C8 0.0492(15) 0.0673(19) 0.0522(16) 0.0156(14) -0.0004(13) -0.0112(14) C9 0.0497(15) 0.0542(16) 0.0554(17) 0.0117(13) -0.0058(12) 0.0035(12) C10 0.0620(17) 0.073(2) 0.0632(19) 0.0111(16) 0.0023(15) 0.0034(15) C11 0.092(3) 0.089(2) 0.0561(19) 0.0057(18) 0.0016(18) 0.020(2) C12 0.091(3) 0.080(2) 0.069(2) -0.0049(18) -0.029(2) 0.022(2) C13 0.0609(19) 0.081(2) 0.084(2) 0.0026(19) -0.0240(18) 0.0040(16) C14 0.0497(15) 0.074(2) 0.0653(19) 0.0098(16) -0.0078(14) 0.0006(14) C15 0.0592(17) 0.073(2) 0.081(2) 0.0367(18) -0.0103(16) -0.0095(16) C16 0.062(2) 0.078(2) 0.112(3) 0.041(2) -0.0007(19) -0.0069(17) Cl1 0.0761(7) 0.0942(8) 0.2364(18) 0.0678(9) 0.0301(8) 0.0171(6) N1 0.0575(14) 0.0801(17) 0.0532(14) 0.0195(13) -0.0064(11) -0.0160(13) N2 0.0612(15) 0.0713(17) 0.0634(16) -0.0009(13) 0.0049(12) -0.0098(13) O1 0.105(2) 0.168(3) 0.0756(17) 0.0403(18) -0.0377(16) -0.033(2) 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_ _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 C2 C1 C6 119.0(5) . . ? C2 C1 H1 120.5 . . ? C6 C1 H1 120.5 . . ? C1 C2 C3 119.4(6) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 121.9(5) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 119.5(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 119.7(5) . . ? C4 C5 C7 120.2(5) . . ? C6 C5 C7 120.1(3) . . ? N2 C6 C1 117.9(4) . . ? N2 C6 C5 121.6(4) . . ? C1 C6 C5 120.5(4) . . ? O1 C7 N1 120.5(4) . . ? O1 C7 C5 124.9(4) . . ? N1 C7 C5 114.6(3) . . ? N2 C8 N1 124.5(3) . . ? N2 C8 C9 116.9(3) . . ? N1 C8 C9 118.5(3) . . ? C10 C9 C14 118.9(3) . . ? C10 C9 C8 121.9(3) . . ? C14 C9 C8 119.0(3) . . ? C11 C10 C9 119.8(3) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.0(3) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 120.9(3) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? N1 C15 C16 110.6(3) . . ? N1 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 Cl1 110.0(2) . . ? C15 C16 H16A 109.7 . . ? Cl1 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? Cl1 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? C8 N1 C7 121.6(3) . . ? C8 N1 C15 123.1(3) . . ? C7 N1 C15 115.3(3) . . ? C8 N2 C6 117.5(3) . . ? 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 C2 1.399(7) . ? C1 C6 1.404(6) . ? C1 H1 0.9300 . ? C2 C3 1.408(8) . ? C2 H2 0.9300 . ? C3 C4 1.361(8) . ? C3 H3 0.9300 . ? C4 C5 1.402(5) . ? C4 H4 0.9300 . ? C5 C6 1.409(6) . ? C5 C7 1.436(6) . ? C6 N2 1.390(4) . ? C7 O1 1.222(4) . ? C7 N1 1.399(4) . ? C8 N2 1.295(4) . ? C8 N1 1.387(4) . ? C8 C9 1.486(4) . ? C9 C10 1.388(4) . ? C9 C14 1.391(4) . ? C10 C11 1.385(5) . ? C10 H10 0.9300 . ? C11 C12 1.382(6) . ? C11 H11 0.9300 . ? C12 C13 1.366(5) . ? C12 H12 0.9300 . ? C13 C14 1.374(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 N1 1.466(4) . ? C15 C16 1.524(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 Cl1 1.763(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 C6 C1 C2 C3 0.5(6) . . . . ? C1 C2 C3 C4 -0.8(7) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C3 C4 C5 C7 -178.1(4) . . . . ? C2 C1 C6 N2 179.0(3) . . . . ? C2 C1 C6 C5 0.5(5) . . . . ? C4 C5 C6 N2 -179.7(3) . . . . ? C7 C5 C6 N2 -0.7(5) . . . . ? C4 C5 C6 C1 -1.3(5) . . . . ? C7 C5 C6 C1 177.8(3) . . . . ? C4 C5 C7 O1 -2.9(5) . . . . ? C6 C5 C7 O1 178.0(3) . . . . ? C4 C5 C7 N1 176.7(3) . . . . ? C6 C5 C7 N1 -2.4(4) . . . . ? N2 C8 C9 C10 -109.5(3) . . . . ? N1 C8 C9 C10 71.0(4) . . . . ? N2 C8 C9 C14 65.7(4) . . . . ? N1 C8 C9 C14 -113.7(3) . . . . ? C14 C9 C10 C11 -0.1(4) . . . . ? C8 C9 C10 C11 175.1(3) . . . . ? C9 C10 C11 C12 1.4(5) . . . . ? C10 C11 C12 C13 -1.5(5) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? C12 C13 C14 C9 1.0(5) . . . . ? C10 C9 C14 C13 -1.0(5) . . . . ? C8 C9 C14 C13 -176.4(3) . . . . ? N1 C15 C16 Cl1 -177.5(2) . . . . ? N2 C8 N1 C7 -2.6(4) . . . . ? C9 C8 N1 C7 176.9(2) . . . . ? N2 C8 N1 C15 -178.7(3) . . . . ? C9 C8 N1 C15 0.7(4) . . . . ? O1 C7 N1 C8 -176.4(3) . . . . ? C5 C7 N1 C8 4.0(4) . . . . ? O1 C7 N1 C15 0.0(4) . . . . ? C5 C7 N1 C15 -179.6(3) . . . . ? C16 C15 N1 C8 -105.7(3) . . . . ? C16 C15 N1 C7 77.9(3) . . . . ? N1 C8 N2 C6 -0.7(4) . . . . ? C9 C8 N2 C6 179.8(2) . . . . ? C1 C6 N2 C8 -176.2(3) . . . . ? C5 C6 N2 C8 2.3(4) . . . . ?