#------------------------------------------------------------------------------ #$Date: 2020-04-05 14:00:31 +0300 (Sun, 05 Apr 2020) $ #$Revision: 250328 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239974.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_7239974 loop_ _publ_author_name 'Yue, Jing' 'Ma, Xi-Tao' 'Liu, Xiong-Li' 'Wang, Jun-Xin' 'Liu, Xiong-Wei' 'Zhou, Ying' _publ_section_title ; Ammonium hydroxide as the ultimate amino source for the synthesis of N-unprotected 3-tetrasubstituted aminooxindoles via catalyst-free direct amination ; _journal_issue 6 _journal_name_full 'Green Chemistry' _journal_page_first 1837 _journal_paper_doi 10.1039/D0GC00130A _journal_volume 22 _journal_year 2020 _chemical_formula_moiety 'C16 H15 Cl N2 O' _chemical_formula_sum 'C16 H15 Cl N2 O' _chemical_formula_weight 286.75 _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2019-04-29 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-30 deposited with the CCDC. 2020-02-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.906(13) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.8233(13) _cell_length_b 10.2114(7) _cell_length_c 12.0326(13) _cell_measurement_reflns_used 2341 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 28.9310 _cell_measurement_theta_min 2.6890 _cell_volume 1405.0(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 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_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -60.00 37.00 1.00 4.00 -- 11.74 -57.00-150.00 97 2 \w -15.00 77.00 1.00 4.00 -- 11.74 57.00 0.00 92 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0031270000 _diffrn_orient_matrix_UB_12 0.0436623000 _diffrn_orient_matrix_UB_13 0.0441944000 _diffrn_orient_matrix_UB_21 -0.0615055000 _diffrn_orient_matrix_UB_22 -0.0088801000 _diffrn_orient_matrix_UB_23 -0.0271239000 _diffrn_orient_matrix_UB_31 0.0077977000 _diffrn_orient_matrix_UB_32 -0.0533382000 _diffrn_orient_matrix_UB_33 0.0407812000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_unetI/netI 0.0468 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5918 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.996 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 2.674 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.268 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.54222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.272 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 2474 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0437 _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^)+(0.0393P)^2^+0.8848P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.1027 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2021 _reflns_number_total 2474 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL as-11_a.res in P2(1)/c as-11.res created by SHELXL-2018/3 at 11:08:11 on 29-Apr-2019 REM Old TITL AS-11 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.117, Rweak 0.262, Alpha 0.026 REM 0.574 for 172 systematic absences, Orientation as input REM Formula found by SHELXT: C16 N2 O Cl CELL 0.71073 12.8233 10.2114 12.0326 90 116.906 90 ZERR 4 0.0013 0.0007 0.0013 0 0.013 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 64 60 4 8 4 L.S. 20 PLAN 20 BOND $h list 4 fmap 2 53 acta OMIT -3 50 REM REM REM WGHT 0.039300 0.884800 FVAR 0.49035 CL1 3 0.180864 0.211400 0.581978 11.00000 0.02911 0.01564 = 0.02441 0.00035 0.01007 0.00103 O1 5 0.095375 0.925222 0.451858 11.00000 0.02707 0.01868 = 0.01491 0.00432 0.01146 0.00409 N1 4 0.115977 0.701094 0.444562 11.00000 0.02181 0.01876 = 0.00695 -0.00036 0.00744 0.00108 AFIX 43 H1 2 0.102671 0.693381 0.368105 11.00000 -1.20000 AFIX 0 N2 4 0.074259 0.847077 0.684364 11.00000 0.02324 0.01916 = 0.01417 0.00264 0.01070 0.00529 C2 1 0.139608 0.595417 0.527795 11.00000 0.01443 0.01756 = 0.01143 0.00236 0.00646 0.00028 C10 1 0.366255 0.804538 0.674738 11.00000 0.01866 0.02008 = 0.01020 -0.00387 0.00366 -0.00389 C8 1 0.116949 0.817064 0.500937 11.00000 0.01497 0.01944 = 0.01268 0.00088 0.00747 0.00038 C3 1 0.146704 0.464062 0.505469 11.00000 0.01913 0.01948 = 0.01453 -0.00327 0.00916 -0.00165 AFIX 43 H3 2 0.135661 0.433683 0.428039 11.00000 -1.20000 AFIX 0 C1 1 0.156907 0.642450 0.643709 11.00000 0.01456 0.01912 = 0.01247 0.00076 0.00647 0.00181 C6 1 0.179460 0.555435 0.740144 11.00000 0.02242 0.02331 = 0.01031 0.00036 0.00846 0.00125 AFIX 43 H6 2 0.190141 0.585690 0.817487 11.00000 -1.20000 AFIX 0 C7 1 0.153867 0.789972 0.639959 11.00000 0.02020 0.01693 = 0.00910 0.00083 0.00719 0.00200 C15 1 0.391876 0.878895 0.593130 11.00000 0.02610 0.01520 = 0.01827 -0.00192 0.00710 -0.00115 AFIX 43 H15 2 0.356001 0.959849 0.566263 11.00000 -1.20000 AFIX 0 C9 1 0.277017 0.849436 0.716468 11.00000 0.02262 0.01814 = 0.01138 -0.00060 0.00513 0.00014 AFIX 23 H9A 2 0.271067 0.944116 0.710341 11.00000 -1.20000 H9B 2 0.304631 0.826212 0.803416 11.00000 -1.20000 AFIX 0 C5 1 0.185952 0.422344 0.720027 11.00000 0.02292 0.02110 = 0.01539 0.00652 0.00845 0.00315 AFIX 43 H5 2 0.200091 0.362576 0.783594 11.00000 -1.20000 AFIX 0 C4 1 0.171245 0.379346 0.604821 11.00000 0.01651 0.01507 = 0.02285 -0.00014 0.00875 -0.00131 C13 1 0.524815 0.713424 0.587707 11.00000 0.01939 0.02684 = 0.01515 -0.00603 0.00578 -0.00395 C12 1 0.499388 0.639215 0.669216 11.00000 0.01941 0.02309 = 0.01852 0.00162 0.00547 0.00409 AFIX 43 H12 2 0.535008 0.558038 0.695444 11.00000 -1.20000 AFIX 0 C11 1 0.422083 0.683622 0.712234 11.00000 0.02244 0.02567 = 0.01196 0.00373 0.00626 0.00064 AFIX 43 H11 2 0.407139 0.631938 0.767060 11.00000 -1.20000 AFIX 0 C14 1 0.470096 0.834063 0.551293 11.00000 0.02835 0.02362 = 0.01686 -0.00020 0.01149 -0.00496 AFIX 43 H14 2 0.486209 0.886166 0.497548 11.00000 -1.20000 AFIX 0 C16 1 0.608542 0.663548 0.540930 11.00000 0.02984 0.03298 = 0.03003 -0.00373 0.01713 -0.00167 AFIX 137 H16A 2 0.685715 0.657884 0.609184 11.00000 -1.50000 H16B 2 0.609188 0.722640 0.479192 11.00000 -1.50000 H16C 2 0.584002 0.578382 0.504647 11.00000 -1.50000 AFIX 0 H2A 2 0.066439 0.929097 0.665700 11.00000 0.02387 H2B 2 0.002653 0.811173 0.643511 11.00000 0.03834 HKLF 4 REM as-11_a.res in P2(1)/c REM wR2 = 0.1027, GooF = S = 1.022, Restrained GooF = 1.022 for all data REM R1 = 0.0437 for 2021 Fo > 4sig(Fo) and 0.0562 for all 2474 data REM 190 parameters refined using 0 restraints END WGHT 0.0393 0.8817 REM Highest difference peak 0.272, deepest hole -0.322, 1-sigma level 0.057 Q1 1 0.0919 0.2041 0.5433 11.00000 0.05 0.27 Q2 1 0.1631 0.7188 0.6523 11.00000 0.05 0.27 Q3 1 0.2174 0.8171 0.6831 11.00000 0.05 0.27 Q4 1 0.2809 0.2102 0.6342 11.00000 0.05 0.25 Q5 1 0.6757 0.7265 0.5417 11.00000 0.05 0.24 Q6 1 0.3584 0.8214 0.6151 11.00000 0.05 0.23 Q7 1 0.3268 0.8248 0.6948 11.00000 0.05 0.21 Q8 1 0.3795 0.7410 0.6731 11.00000 0.05 0.21 Q9 1 0.4089 0.7782 0.7108 11.00000 0.05 0.20 Q10 1 0.5170 0.7871 0.6034 11.00000 0.05 0.20 Q11 1 0.6489 0.5756 0.5752 11.00000 0.05 0.20 Q12 1 0.2245 0.6059 0.6970 11.00000 0.05 0.20 Q13 1 0.1387 0.8079 0.5804 11.00000 0.05 0.19 Q14 1 0.4007 0.8450 0.5366 11.00000 0.05 0.18 Q15 1 -0.0206 0.8645 0.4642 11.00000 0.05 0.18 Q16 1 0.1833 0.3193 0.5946 11.00000 0.05 0.17 Q17 1 0.1655 0.4057 0.4115 11.00000 0.05 0.17 Q18 1 0.1274 0.9236 0.3840 11.00000 0.05 0.17 Q19 1 0.0664 0.7996 0.7334 11.00000 0.05 0.17 Q20 1 0.1672 0.6125 0.5933 11.00000 0.05 0.17 REM The information below was added by Olex2. REM REM R1 = 0.0437 for 2021 Fo > 4sig(Fo) and 0.0562 for all 7272 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.27, deepest hole -0.32 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0562 REM R1_gt = 0.0437 REM wR_ref = 0.1027 REM GOOF = 1.022 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 7272 REM Reflections_gt = 2021 REM Parameters = n/a REM Hole = -0.32 REM Peak = 0.27 REM Flack = n/a ; _cod_data_source_file d0gc00130a2.cif _cod_data_source_block as-11 _cod_depositor_comments 'Adding full bibliography for 7239973--7239974.cif.' _cod_database_code 7239974 _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. ; _reflns_odcompleteness_completeness 99.90 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: N1(H1), C3(H3), C6(H6), C15(H15), C5(H5), C12(H12), C11(H11), C14(H14) 2.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.341 _oxdiff_exptl_absorpt_empirical_full_min 0.556 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 Cl1 Cl 0.18086(5) 0.21140(5) 0.58198(5) 0.02383(18) Uani 1 1 d . . . . . O1 O 0.09538(13) 0.92522(14) 0.45186(13) 0.0195(4) Uani 1 1 d . . . . . N1 N 0.11598(15) 0.70109(16) 0.44456(16) 0.0155(4) Uani 1 1 d . . . . . H1 H 0.102671 0.693381 0.368105 0.019 Uiso 1 1 calc R . . . . N2 N 0.07426(18) 0.8471(2) 0.68436(17) 0.0180(4) Uani 1 1 d . . . . . C2 C 0.13961(18) 0.5954(2) 0.52779(19) 0.0142(5) Uani 1 1 d . . . . . C10 C 0.36625(19) 0.8045(2) 0.67474(19) 0.0174(5) Uani 1 1 d . . . . . C8 C 0.11695(18) 0.8171(2) 0.50094(19) 0.0152(5) Uani 1 1 d . . . . . C3 C 0.14670(18) 0.4641(2) 0.5055(2) 0.0171(5) Uani 1 1 d . . . . . H3 H 0.135661 0.433683 0.428039 0.021 Uiso 1 1 calc R . . . . C1 C 0.15691(18) 0.6424(2) 0.64371(19) 0.0152(5) Uani 1 1 d . . . . . C6 C 0.17946(18) 0.5554(2) 0.7401(2) 0.0183(5) Uani 1 1 d . . . . . H6 H 0.190141 0.585690 0.817487 0.022 Uiso 1 1 calc R . . . . C7 C 0.15387(18) 0.7900(2) 0.63996(19) 0.0152(5) Uani 1 1 d . . . . . C15 C 0.39188(19) 0.8789(2) 0.5931(2) 0.0210(5) Uani 1 1 d . . . . . H15 H 0.356001 0.959849 0.566263 0.025 Uiso 1 1 calc R . . . . C9 C 0.27702(19) 0.8494(2) 0.7165(2) 0.0184(5) Uani 1 1 d . . . . . H9A H 0.271067 0.944116 0.710341 0.022 Uiso 1 1 calc R . . . . H9B H 0.304631 0.826212 0.803416 0.022 Uiso 1 1 calc R . . . . C5 C 0.18595(19) 0.4223(2) 0.7200(2) 0.0199(5) Uani 1 1 d . . . . . H5 H 0.200091 0.362576 0.783594 0.024 Uiso 1 1 calc R . . . . C4 C 0.17124(18) 0.3793(2) 0.6048(2) 0.0182(5) Uani 1 1 d . . . . . C13 C 0.52481(19) 0.7134(2) 0.5877(2) 0.0212(5) Uani 1 1 d . . . . . C12 C 0.49939(19) 0.6392(2) 0.6692(2) 0.0215(5) Uani 1 1 d . . . . . H12 H 0.535008 0.558038 0.695444 0.026 Uiso 1 1 calc R . . . . C11 C 0.42208(19) 0.6836(2) 0.7122(2) 0.0206(5) Uani 1 1 d . . . . . H11 H 0.407139 0.631938 0.767060 0.025 Uiso 1 1 calc R . . . . C14 C 0.4701(2) 0.8341(2) 0.5513(2) 0.0225(5) Uani 1 1 d . . . . . H14 H 0.486209 0.886166 0.497548 0.027 Uiso 1 1 calc R . . . . C16 C 0.6085(2) 0.6635(2) 0.5409(2) 0.0296(6) Uani 1 1 d . . . . . H16A H 0.685715 0.657884 0.609184 0.044 Uiso 1 1 calc GR . . . . H16B H 0.609188 0.722640 0.479192 0.044 Uiso 1 1 calc GR . . . . H16C H 0.584002 0.578382 0.504647 0.044 Uiso 1 1 calc GR . . . . H2A H 0.066(2) 0.929(3) 0.666(2) 0.024(7) Uiso 1 1 d . . . . . H2B H 0.003(3) 0.811(3) 0.644(3) 0.038(8) Uiso 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 Cl1 0.0291(3) 0.0156(3) 0.0244(3) 0.0004(2) 0.0101(3) 0.0010(2) O1 0.0271(9) 0.0187(8) 0.0149(8) 0.0043(6) 0.0115(7) 0.0041(7) N1 0.0218(10) 0.0188(10) 0.0069(9) -0.0004(7) 0.0074(8) 0.0011(8) N2 0.0232(11) 0.0192(11) 0.0142(10) 0.0026(8) 0.0107(9) 0.0053(9) C2 0.0144(10) 0.0176(11) 0.0114(11) 0.0024(9) 0.0065(9) 0.0003(9) C10 0.0187(11) 0.0201(12) 0.0102(11) -0.0039(9) 0.0037(9) -0.0039(9) C8 0.0150(11) 0.0194(12) 0.0127(11) 0.0009(9) 0.0075(9) 0.0004(9) C3 0.0191(11) 0.0195(12) 0.0145(12) -0.0033(9) 0.0092(10) -0.0017(10) C1 0.0146(10) 0.0191(11) 0.0125(11) 0.0008(9) 0.0065(9) 0.0018(9) C6 0.0224(12) 0.0233(12) 0.0103(11) 0.0004(9) 0.0085(10) 0.0013(10) C7 0.0202(11) 0.0169(11) 0.0091(11) 0.0008(8) 0.0072(9) 0.0020(9) C15 0.0261(12) 0.0152(11) 0.0183(13) -0.0019(9) 0.0071(10) -0.0012(10) C9 0.0226(12) 0.0181(11) 0.0114(11) -0.0006(9) 0.0051(10) 0.0001(10) C5 0.0229(12) 0.0211(12) 0.0154(12) 0.0065(9) 0.0084(10) 0.0031(10) C4 0.0165(11) 0.0151(11) 0.0228(13) -0.0001(9) 0.0087(10) -0.0013(9) C13 0.0194(12) 0.0268(13) 0.0152(12) -0.0060(10) 0.0058(10) -0.0040(10) C12 0.0194(12) 0.0231(12) 0.0185(13) 0.0016(10) 0.0055(10) 0.0041(10) C11 0.0224(12) 0.0257(12) 0.0120(12) 0.0037(9) 0.0063(10) 0.0006(10) C14 0.0284(13) 0.0236(12) 0.0169(12) -0.0002(10) 0.0115(11) -0.0050(11) C16 0.0298(14) 0.0330(14) 0.0300(15) -0.0037(11) 0.0171(12) -0.0017(11) 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 C2 N1 H1 124.4 . . ? C8 N1 H1 124.4 . . ? C8 N1 C2 111.19(18) . . ? C7 N2 H2A 108.0(17) . . ? C7 N2 H2B 110.1(17) . . ? H2A N2 H2B 106(2) . . ? C3 C2 N1 128.2(2) . . ? C3 C2 C1 122.35(19) . . ? C1 C2 N1 109.44(18) . . ? C15 C10 C9 121.57(19) . . ? C15 C10 C11 117.4(2) . . ? C11 C10 C9 121.0(2) . . ? O1 C8 N1 126.5(2) . . ? O1 C8 C7 125.19(19) . . ? N1 C8 C7 108.25(17) . . ? C2 C3 H3 121.7 . . ? C2 C3 C4 116.5(2) . . ? C4 C3 H3 121.7 . . ? C2 C1 C7 108.91(17) . . ? C6 C1 C2 119.7(2) . . ? C6 C1 C7 131.26(19) . . ? C1 C6 H6 120.4 . . ? C1 C6 C5 119.2(2) . . ? C5 C6 H6 120.4 . . ? N2 C7 C8 113.57(17) . . ? N2 C7 C1 113.48(18) . . ? N2 C7 C9 108.52(17) . . ? C8 C7 C9 107.72(17) . . ? C1 C7 C8 101.70(16) . . ? C1 C7 C9 111.64(17) . . ? C10 C15 H15 119.5 . . ? C14 C15 C10 121.0(2) . . ? C14 C15 H15 119.5 . . ? C10 C9 C7 113.89(17) . . ? C10 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C7 C9 H9A 108.8 . . ? C7 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C6 C5 H5 120.2 . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5 120.2 . . ? C3 C4 Cl1 118.62(17) . . ? C5 C4 Cl1 118.76(17) . . ? C5 C4 C3 122.6(2) . . ? C12 C13 C16 120.9(2) . . ? C14 C13 C12 117.4(2) . . ? C14 C13 C16 121.7(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 C13 121.4(2) . . ? C11 C12 H12 119.3 . . ? C10 C11 H11 119.4 . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C15 C14 H14 119.2 . . ? C13 C14 C15 121.6(2) . . ? C13 C14 H14 119.2 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C4 1.750(2) . ? O1 C8 1.224(2) . ? N1 H1 0.8600 . ? N1 C2 1.409(3) . ? N1 C8 1.362(3) . ? N2 C7 1.470(3) . ? N2 H2A 0.86(3) . ? N2 H2B 0.90(3) . ? C2 C3 1.379(3) . ? C2 C1 1.395(3) . ? C10 C15 1.393(3) . ? C10 C9 1.514(3) . ? C10 C11 1.396(3) . ? C8 C7 1.543(3) . ? C3 H3 0.9300 . ? C3 C4 1.391(3) . ? C1 C6 1.384(3) . ? C1 C7 1.507(3) . ? C6 H6 0.9300 . ? C6 C5 1.390(3) . ? C7 C9 1.547(3) . ? C15 H15 0.9300 . ? C15 C14 1.388(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C5 H5 0.9300 . ? C5 C4 1.383(3) . ? C13 C12 1.390(3) . ? C13 C14 1.387(3) . ? C13 C16 1.509(3) . ? C12 H12 0.9300 . ? C12 C11 1.386(3) . ? C11 H11 0.9300 . ? C14 H14 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ?