#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:38:17 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271187 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061021.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_7061021 loop_ _publ_author_name 'Capozzi, Maria Annunziata M.' 'Alvarez-Larena, Angel' 'Piniella Febrer, Joan F.' 'Cardellicchio, Cosimo' _publ_section_title ; A combined structural and computational investigation of aminobenzylnaphthol compounds derived from the Betti reaction using valine methyl ester ; _journal_issue 44 _journal_name_full 'New Journal of Chemistry' _journal_page_first 20735 _journal_page_last 20742 _journal_paper_doi 10.1039/D1NJ03538J _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C23 H24 Cl N O3' _chemical_formula_sum 'C23 H24 Cl N O3' _chemical_formula_weight 397.88 _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 mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2021-03-22 deposited with the CCDC. 2021-10-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.9280(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.0861(7) _cell_length_b 9.8938(5) _cell_length_c 16.1156(8) _cell_measurement_reflns_used 5027 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 49.86 _cell_measurement_theta_min 4.84 _cell_volume 2078.79(18) _computing_cell_refinement 'SAINT 5.0 (Bruker)' _computing_data_collection 'SMART 5.6 (Bruker)' _computing_data_reduction 'SAINT 5.0 (Bruker)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXTL-NT 6.1 (Bruker)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 8.13 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.932 _diffrn_measurement_device_type 'Bruker SMART-APEX diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_unetI/netI 0.0270 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.932 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 16222 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.932 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 28.747 _diffrn_reflns_theta_min 1.926 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.207 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, 2.05' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.660 _exptl_crystal_size_mid 0.440 _exptl_crystal_size_min 0.220 _refine_diff_density_max 0.241 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.034 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 5033 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0491 _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^)+(0.0661P)^2^+0.3706P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1303 _refine_ls_wR_factor_ref 0.1450 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3514 _reflns_number_total 5033 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03538j2.cif _cod_data_source_block cb107 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7061017--7061021.cif. ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7061021 _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_estimated_absorpt_t_min 0.876 _shelx_estimated_absorpt_t_max 0.956 _shelx_res_file ; TITL cb107 in P2(1)/n shelx.res created by SHELXL-2016/6 at 19:27:33 on 02-Mar-2021 CELL 0.71073 13.0861 9.8938 16.1156 90.000 94.928 90.000 ZERR 4.00 0.0007 0.0005 0.0008 0.000 0.001 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O Cl UNIT 92 96 4 12 4 TEMP 23 SIZE 0.66 0.44 0.22 L.S. 10 ACTA 50 BOND FMAP 2 PLAN 3 WGHT 0.066100 0.370600 FVAR 0.46365 MOLE 1 C1 1 0.036498 0.421490 0.729225 11.00000 0.04529 0.04107 = 0.05473 0.00106 -0.00198 0.00219 AFIX 13 H1 2 -0.029547 0.386561 0.705041 11.00000 -1.20000 AFIX 0 C2 1 0.033371 0.574329 0.719640 11.00000 0.05551 0.04051 = 0.04668 0.00126 -0.00093 0.00147 C3 1 0.122787 0.647835 0.721745 11.00000 0.06014 0.04906 = 0.05380 -0.00073 -0.00673 -0.00300 C4 1 0.121567 0.789474 0.715007 11.00000 0.07906 0.05127 = 0.07064 -0.00120 -0.00827 -0.01633 AFIX 43 H4 2 0.183076 0.837039 0.718186 11.00000 -1.20000 AFIX 0 C5 1 0.031702 0.857055 0.703945 11.00000 0.10398 0.03915 = 0.06685 -0.00200 -0.00377 -0.00039 AFIX 43 H5 2 0.032163 0.950823 0.699958 11.00000 -1.20000 AFIX 0 C6 1 -0.062243 0.788067 0.698380 11.00000 0.08171 0.04416 = 0.05065 -0.00042 0.00495 0.01250 C7 1 -0.156971 0.856744 0.683363 11.00000 0.10242 0.05641 = 0.07138 0.00207 0.00892 0.03120 AFIX 43 H7 2 -0.156927 0.950230 0.677348 11.00000 -1.20000 AFIX 0 C8 1 -0.247267 0.790185 0.677551 11.00000 0.07901 0.08877 = 0.08684 0.00562 0.01216 0.04211 AFIX 43 H8 2 -0.308484 0.837362 0.667072 11.00000 -1.20000 AFIX 0 C9 1 -0.248208 0.649935 0.687377 11.00000 0.05815 0.08778 = 0.09246 0.01154 0.01545 0.01636 AFIX 43 H9 2 -0.310495 0.604157 0.684082 11.00000 -1.20000 AFIX 0 C10 1 -0.158879 0.579195 0.701752 11.00000 0.05856 0.05808 = 0.07650 0.01058 0.01373 0.01050 AFIX 43 H10 2 -0.161513 0.485870 0.708124 11.00000 -1.20000 AFIX 0 C11 1 -0.062434 0.644538 0.707178 11.00000 0.06086 0.04665 = 0.04432 0.00280 0.00520 0.00859 C12 1 0.051326 0.370345 0.818581 11.00000 0.04071 0.04613 = 0.05611 0.00505 0.00335 0.00286 C13 1 0.080636 0.451578 0.885621 11.00000 0.06775 0.05172 = 0.05890 0.00430 0.00299 -0.00259 AFIX 43 H13 2 0.094237 0.542536 0.877035 11.00000 -1.20000 AFIX 0 C14 1 0.090232 0.399743 0.966015 11.00000 0.07887 0.06967 = 0.05558 0.00157 0.00327 0.00101 AFIX 43 H14 2 0.110754 0.455334 1.010918 11.00000 -1.20000 AFIX 0 C15 1 0.069207 0.266057 0.978582 11.00000 0.06529 0.07307 = 0.05958 0.01889 0.01022 0.00713 C16 1 0.040714 0.182958 0.913473 11.00000 0.08140 0.05678 = 0.07636 0.01833 0.00936 -0.00215 AFIX 43 H16 2 0.027260 0.092096 0.922538 11.00000 -1.20000 AFIX 0 C17 1 0.032014 0.235136 0.833791 11.00000 0.07165 0.04948 = 0.06510 0.00505 0.00175 -0.00450 AFIX 43 H17 2 0.012742 0.178299 0.789208 11.00000 -1.20000 AFIX 0 C18 1 0.083724 0.358409 0.590540 11.00000 0.06067 0.04095 = 0.05249 0.00240 -0.00314 0.00317 AFIX 13 H18 2 0.062389 0.449588 0.572726 11.00000 -1.20000 AFIX 0 C19 1 0.168272 0.313016 0.536467 11.00000 0.07689 0.08213 = 0.05368 -0.00237 0.00149 0.01796 AFIX 13 H19 2 0.139888 0.318384 0.478275 11.00000 -1.20000 AFIX 0 C20 1 0.259663 0.407209 0.546034 11.00000 0.07933 0.19479 = 0.10554 -0.03817 0.03100 -0.02534 AFIX 137 H20A 2 0.296064 0.393812 0.599697 11.00000 -1.50000 H20B 2 0.236450 0.499140 0.541175 11.00000 -1.50000 H20C 2 0.304440 0.388418 0.503297 11.00000 -1.50000 AFIX 0 C21 1 0.200294 0.168540 0.552779 11.00000 0.18472 0.12733 = 0.09207 0.00867 0.03007 0.09640 AFIX 137 H21A 2 0.251422 0.143772 0.516266 11.00000 -1.50000 H21B 2 0.141768 0.110426 0.542880 11.00000 -1.50000 H21C 2 0.228100 0.159344 0.609588 11.00000 -1.50000 AFIX 0 C22 1 -0.008509 0.266317 0.575742 11.00000 0.07692 0.04491 = 0.05780 -0.00327 -0.00537 -0.00358 C23 1 -0.160485 0.220748 0.492508 11.00000 0.09379 0.13599 = 0.09408 0.00236 -0.01959 -0.04838 AFIX 137 H23A 2 -0.140861 0.129819 0.480454 11.00000 -1.50000 H23B 2 -0.201499 0.257174 0.445517 11.00000 -1.50000 H23C 2 -0.199453 0.220863 0.540333 11.00000 -1.50000 AFIX 0 CL1 5 0.077489 0.203696 1.080217 11.00000 0.13193 0.10932 = 0.06785 0.03278 0.01388 0.00410 N1 3 0.117348 0.364259 0.679672 11.00000 0.05357 0.04317 = 0.05134 0.00244 -0.00246 0.00765 H1N 2 0.132015 0.284131 0.696843 11.00000 -1.20000 O1 4 0.217207 0.588138 0.730425 11.00000 0.05271 0.06609 = 0.08941 -0.00344 -0.00970 -0.00556 H1O 2 0.202904 0.502674 0.713014 11.00000 -1.50000 O2 4 -0.026126 0.171845 0.618845 11.00000 0.13308 0.05710 = 0.08898 0.01617 -0.02103 -0.03356 O3 4 -0.069206 0.303000 0.509474 11.00000 0.07217 0.08258 = 0.06548 0.00750 -0.01333 -0.01624 HKLF 4 REM cb107 in P2(1)/n REM R1 = 0.0491 for 3514 Fo > 4sig(Fo) and 0.0716 for all 5033 data REM 262 parameters refined using 0 restraints END WGHT 0.0662 0.3708 REM Highest difference peak 0.241, deepest hole -0.247, 1-sigma level 0.034 Q1 1 0.0337 0.4983 0.7240 11.00000 0.05 0.24 Q2 1 0.1216 0.2839 1.0921 11.00000 0.05 0.24 Q3 1 -0.0598 0.7176 0.6943 11.00000 0.05 0.21 ; _shelx_res_checksum 27850 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 C1 C 0.03650(11) 0.42149(14) 0.72922(9) 0.0474(3) Uani 1 1 d . . . . . H1 H -0.029547 0.386561 0.705041 0.057 Uiso 1 1 calc R U . . . C2 C 0.03337(12) 0.57433(14) 0.71964(9) 0.0479(3) Uani 1 1 d . . . . . C3 C 0.12279(13) 0.64784(16) 0.72174(10) 0.0550(4) Uani 1 1 d . . . . . C4 C 0.12157(16) 0.78947(17) 0.71501(12) 0.0678(5) Uani 1 1 d . . . . . H4 H 0.183076 0.837039 0.718186 0.081 Uiso 1 1 calc R U . . . C5 C 0.03170(17) 0.85705(17) 0.70394(12) 0.0706(5) Uani 1 1 d . . . . . H5 H 0.032163 0.950823 0.699958 0.085 Uiso 1 1 calc R U . . . C6 C -0.06224(15) 0.78807(16) 0.69838(10) 0.0589(4) Uani 1 1 d . . . . . C7 C -0.15697(19) 0.8567(2) 0.68336(13) 0.0767(6) Uani 1 1 d . . . . . H7 H -0.156927 0.950230 0.677348 0.092 Uiso 1 1 calc R U . . . C8 C -0.24727(19) 0.7902(2) 0.67755(14) 0.0846(7) Uani 1 1 d . . . . . H8 H -0.308484 0.837362 0.667072 0.101 Uiso 1 1 calc R U . . . C9 C -0.24821(15) 0.6499(2) 0.68738(14) 0.0789(6) Uani 1 1 d . . . . . H9 H -0.310495 0.604157 0.684082 0.095 Uiso 1 1 calc R U . . . C10 C -0.15888(13) 0.57920(19) 0.70175(12) 0.0639(4) Uani 1 1 d . . . . . H10 H -0.161513 0.485870 0.708124 0.077 Uiso 1 1 calc R U . . . C11 C -0.06243(12) 0.64454(15) 0.70718(9) 0.0506(4) Uani 1 1 d . . . . . C12 C 0.05133(11) 0.37035(15) 0.81858(10) 0.0477(3) Uani 1 1 d . . . . . C13 C 0.08064(13) 0.45158(17) 0.88562(11) 0.0596(4) Uani 1 1 d . . . . . H13 H 0.094237 0.542536 0.877035 0.072 Uiso 1 1 calc R U . . . C14 C 0.09023(15) 0.3997(2) 0.96601(11) 0.0682(5) Uani 1 1 d . . . . . H14 H 0.110754 0.455334 1.010918 0.082 Uiso 1 1 calc R U . . . C15 C 0.06921(14) 0.2661(2) 0.97858(12) 0.0657(5) Uani 1 1 d . . . . . C16 C 0.04071(16) 0.18296(19) 0.91347(13) 0.0714(5) Uani 1 1 d . . . . . H16 H 0.027260 0.092096 0.922538 0.086 Uiso 1 1 calc R U . . . C17 C 0.03201(14) 0.23514(17) 0.83379(12) 0.0623(4) Uani 1 1 d . . . . . H17 H 0.012742 0.178299 0.789208 0.075 Uiso 1 1 calc R U . . . C18 C 0.08372(12) 0.35841(15) 0.59054(10) 0.0518(4) Uani 1 1 d . . . . . H18 H 0.062389 0.449588 0.572726 0.062 Uiso 1 1 calc R U . . . C19 C 0.16827(16) 0.3130(2) 0.53647(12) 0.0711(5) Uani 1 1 d . . . . . H19 H 0.139888 0.318384 0.478275 0.085 Uiso 1 1 calc R U . . . C20 C 0.25966(19) 0.4072(4) 0.54603(17) 0.1252(11) Uani 1 1 d . . . . . H20A H 0.296064 0.393812 0.599697 0.188 Uiso 1 1 calc R U . . . H20B H 0.236450 0.499140 0.541175 0.188 Uiso 1 1 calc R U . . . H20C H 0.304440 0.388418 0.503297 0.188 Uiso 1 1 calc R U . . . C21 C 0.2003(3) 0.1685(3) 0.55278(18) 0.1337(13) Uani 1 1 d . . . . . H21A H 0.251422 0.143772 0.516266 0.200 Uiso 1 1 calc R U . . . H21B H 0.141768 0.110426 0.542880 0.200 Uiso 1 1 calc R U . . . H21C H 0.228100 0.159344 0.609588 0.200 Uiso 1 1 calc R U . . . C22 C -0.00851(15) 0.26632(16) 0.57574(11) 0.0605(4) Uani 1 1 d . . . . . C23 C -0.1605(2) 0.2207(3) 0.49251(17) 0.1095(9) Uani 1 1 d . . . . . H23A H -0.140861 0.129819 0.480454 0.164 Uiso 1 1 calc R U . . . H23B H -0.201499 0.257174 0.445517 0.164 Uiso 1 1 calc R U . . . H23C H -0.199453 0.220863 0.540333 0.164 Uiso 1 1 calc R U . . . Cl1 Cl 0.07749(6) 0.20370(7) 1.08022(4) 0.1027(2) Uani 1 1 d . . . . . N1 N 0.11735(10) 0.36426(13) 0.67967(8) 0.0498(3) Uani 1 1 d . . . . . H1N H 0.1320(14) 0.2841(19) 0.6968(11) 0.060 Uiso 1 1 d . U . . . O1 O 0.21721(9) 0.58814(14) 0.73042(9) 0.0703(4) Uani 1 1 d . . . . . H1O H 0.2029(19) 0.503(3) 0.7130(15) 0.105 Uiso 1 1 d . U . . . O2 O -0.02613(14) 0.17184(14) 0.61885(10) 0.0948(5) Uani 1 1 d . . . . . O3 O -0.06921(10) 0.30300(14) 0.50947(8) 0.0745(4) 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 0.0453(8) 0.0411(7) 0.0547(9) 0.0011(6) -0.0020(6) 0.0022(6) C2 0.0555(9) 0.0405(7) 0.0467(8) 0.0013(6) -0.0009(6) 0.0015(6) C3 0.0601(10) 0.0491(8) 0.0538(9) -0.0007(7) -0.0067(7) -0.0030(7) C4 0.0791(12) 0.0513(10) 0.0706(11) -0.0012(8) -0.0083(9) -0.0163(9) C5 0.1040(15) 0.0391(8) 0.0668(11) -0.0020(8) -0.0038(10) -0.0004(9) C6 0.0817(12) 0.0442(8) 0.0506(9) -0.0004(7) 0.0049(8) 0.0125(8) C7 0.1024(16) 0.0564(10) 0.0714(12) 0.0021(9) 0.0089(11) 0.0312(11) C8 0.0790(15) 0.0888(15) 0.0868(15) 0.0056(11) 0.0122(11) 0.0421(12) C9 0.0582(11) 0.0878(14) 0.0925(15) 0.0115(11) 0.0154(10) 0.0164(10) C10 0.0586(10) 0.0581(10) 0.0765(12) 0.0106(8) 0.0137(8) 0.0105(8) C11 0.0609(9) 0.0466(8) 0.0443(8) 0.0028(6) 0.0052(7) 0.0086(7) C12 0.0407(7) 0.0461(8) 0.0561(9) 0.0050(6) 0.0034(6) 0.0029(6) C13 0.0678(10) 0.0517(9) 0.0589(10) 0.0043(7) 0.0030(8) -0.0026(8) C14 0.0789(12) 0.0697(12) 0.0556(10) 0.0016(8) 0.0033(9) 0.0010(9) C15 0.0653(11) 0.0731(12) 0.0596(10) 0.0189(9) 0.0102(8) 0.0071(9) C16 0.0814(13) 0.0568(10) 0.0764(13) 0.0183(9) 0.0094(10) -0.0022(9) C17 0.0717(11) 0.0495(9) 0.0651(11) 0.0050(8) 0.0017(9) -0.0045(8) C18 0.0607(9) 0.0409(7) 0.0525(8) 0.0024(6) -0.0031(7) 0.0032(7) C19 0.0769(13) 0.0821(13) 0.0537(10) -0.0024(9) 0.0015(9) 0.0180(10) C20 0.0793(16) 0.195(3) 0.106(2) -0.038(2) 0.0310(14) -0.0253(18) C21 0.185(3) 0.127(2) 0.0921(18) 0.0087(16) 0.0301(19) 0.096(2) C22 0.0769(11) 0.0449(8) 0.0578(10) -0.0033(7) -0.0054(8) -0.0036(8) C23 0.0938(17) 0.136(2) 0.0941(18) 0.0024(16) -0.0196(14) -0.0484(16) Cl1 0.1319(6) 0.1093(5) 0.0679(3) 0.0328(3) 0.0139(3) 0.0041(4) N1 0.0536(7) 0.0432(6) 0.0513(7) 0.0024(5) -0.0025(5) 0.0076(6) O1 0.0527(7) 0.0661(8) 0.0894(9) -0.0034(7) -0.0097(6) -0.0056(6) O2 0.1331(13) 0.0571(8) 0.0890(10) 0.0162(7) -0.0210(9) -0.0336(8) O3 0.0722(8) 0.0826(9) 0.0655(8) 0.0075(6) -0.0133(6) -0.0162(7) 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 N1 C1 C2 109.72(13) . . ? N1 C1 C12 109.98(11) . . ? C2 C1 C12 115.26(12) . . ? C3 C2 C11 118.65(14) . . ? C3 C2 C1 120.53(14) . . ? C11 C2 C1 120.81(13) . . ? O1 C3 C2 122.28(14) . . ? O1 C3 C4 116.31(15) . . ? C2 C3 C4 121.41(16) . . ? C5 C4 C3 120.50(17) . . ? C4 C5 C6 121.06(16) . . ? C5 C6 C7 121.81(17) . . ? C5 C6 C11 119.14(16) . . ? C7 C6 C11 119.04(18) . . ? C8 C7 C6 121.76(18) . . ? C7 C8 C9 119.56(18) . . ? C10 C9 C8 120.9(2) . . ? C9 C10 C11 121.52(18) . . ? C10 C11 C6 117.25(15) . . ? C10 C11 C2 123.56(14) . . ? C6 C11 C2 119.18(15) . . ? C13 C12 C17 117.89(15) . . ? C13 C12 C1 123.59(14) . . ? C17 C12 C1 118.50(14) . . ? C12 C13 C14 120.93(16) . . ? C15 C14 C13 119.42(17) . . ? C16 C15 C14 121.00(17) . . ? C16 C15 Cl1 120.09(15) . . ? C14 C15 Cl1 118.90(16) . . ? C15 C16 C17 119.16(17) . . ? C16 C17 C12 121.58(17) . . ? N1 C18 C22 110.23(13) . . ? N1 C18 C19 113.44(13) . . ? C22 C18 C19 109.78(14) . . ? C21 C19 C20 111.2(2) . . ? C21 C19 C18 112.47(19) . . ? C20 C19 C18 111.36(17) . . ? O2 C22 O3 123.27(17) . . ? O2 C22 C18 124.62(16) . . ? O3 C22 C18 112.11(14) . . ? C18 N1 C1 111.87(11) . . ? C22 O3 C23 115.13(16) . . ? 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 1.491(2) . ? C1 C2 1.520(2) . ? C1 C12 1.523(2) . ? C2 C3 1.376(2) . ? C2 C11 1.432(2) . ? C3 O1 1.366(2) . ? C3 C4 1.406(2) . ? C4 C5 1.351(3) . ? C5 C6 1.402(3) . ? C6 C7 1.416(3) . ? C6 C11 1.427(2) . ? C7 C8 1.349(3) . ? C8 C9 1.397(3) . ? C9 C10 1.365(3) . ? C10 C11 1.414(2) . ? C12 C13 1.374(2) . ? C12 C17 1.387(2) . ? C13 C14 1.389(2) . ? C14 C15 1.370(3) . ? C15 C16 1.360(3) . ? C15 Cl1 1.7449(18) . ? C16 C17 1.380(3) . ? C18 N1 1.467(2) . ? C18 C22 1.515(2) . ? C18 C19 1.533(2) . ? C19 C21 1.506(3) . ? C19 C20 1.514(3) . ? C22 O2 1.199(2) . ? C22 O3 1.326(2) . ? C23 O3 1.452(2) . ?