#------------------------------------------------------------------------------ #$Date: 2021-09-30 03:44:53 +0300 (Thu, 30 Sep 2021) $ #$Revision: 269388 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060977.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_7060977 loop_ _publ_author_name 'Ahmed, Muhammad Naeem' 'Ghias, Mehreen' 'Ali Shah, Syed' 'Shoaib, Mohammad' 'Tahir, Muhammad Nawaz' 'Ashfaq, Muhammad' 'Ibrahim, Mahmoud A. A.' 'Andleeb, Hina' 'Gil, Diego M.' 'Frontera, Antonio' _publ_section_title ; X-Ray characterization, Hirshfeld surface analysis, DFT calculations, in vitro and in silico lipoxygenase inhibition (LOX) studies of dichlorophenyl substituted 3-hydroxy-chromenones ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04340D _journal_year 2021 _chemical_formula_iupac 'C15 H8 Cl2 O3' _chemical_formula_moiety 'C15 H8 Cl2 O3' _chemical_formula_sum 'C15 H8 Cl2 O3' _chemical_formula_weight 307.11 _chemical_name_systematic ; 2-(2,6-Dichlorophenyl)-3-hydroxy-4H-chromen-4-one ; _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 direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-08-10 deposited with the CCDC. 2021-09-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.017(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6464(5) _cell_length_b 11.3272(7) _cell_length_c 15.5325(10) _cell_measurement_reflns_used 2348 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.532 _cell_measurement_theta_min 2.240 _cell_volume 1320.51(15) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)' _computing_publication_material ; WinGX (Farrugia, 1999) and PLATON (Spek, 2009) ; _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 7.6 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0240 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 10910 _diffrn_reflns_theta_full 27.532 _diffrn_reflns_theta_max 27.532 _diffrn_reflns_theta_min 2.240 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.494 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_correction_T_min 0.820 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.545 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.330 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.043 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3023 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0375 _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^)+(0.0473P)^2^+0.4020P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0968 _refine_ls_wR_factor_ref 0.1058 _reflns_number_gt 2348 _reflns_number_total 3023 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d1nj04340d2.cif _cod_data_source_block OF7uom _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7060977 _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. ; _shelx_res_file ; TITL OF7UOM_0m in P2(1)/n COLORLESS PRISM shelx.res created by SHELXL-2018/3 at 08:53:57 on 10-Aug-2021 CELL 0.71073 7.6464 11.3272 15.5325 90.000 101.017 90.000 ZERR 4.00 0.0005 0.0007 0.0010 0.000 0.003 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H O Cl UNIT 60 32 12 8 L.S. 40 ACTA BOND $H HTAB CONF LIST 4 FMAP 2 PLAN 8 SIZE 0.43 0.34 0.30 OMIT 0 0 2 OMIT -1 1 1 TEMP 23.000 HTAB O3 O2 EQIV $1 -x, -y, -z HTAB O3 O2_$1 WGHT 0.047300 0.402000 FVAR 0.16996 CL1 4 0.234032 0.342766 0.245004 11.00000 0.08048 0.05941 = 0.05128 -0.00102 0.01618 0.00458 CL2 4 0.318043 0.397100 -0.089194 11.00000 0.07572 0.07612 = 0.05706 0.00850 0.01801 -0.00487 O1 3 0.517714 0.249325 0.117441 11.00000 0.03216 0.03672 = 0.05545 -0.00167 0.00010 -0.00248 O2 3 0.211657 -0.042764 0.047585 11.00000 0.04275 0.03124 = 0.05970 -0.00026 -0.00069 -0.00279 O3 3 0.063443 0.180699 0.023938 11.00000 0.03314 0.03074 = 0.09001 0.00007 -0.00745 -0.00013 AFIX 147 H3A 2 0.015067 0.117044 0.010127 11.00000 -1.50000 AFIX 0 C1 1 0.593125 0.139579 0.131281 11.00000 0.03415 0.04171 = 0.03832 0.00027 0.00475 0.00328 C2 1 0.773159 0.137269 0.169308 11.00000 0.03754 0.05737 = 0.05637 -0.00219 -0.00017 -0.00021 AFIX 43 H2 2 0.836249 0.206898 0.184029 11.00000 -1.20000 AFIX 0 C3 1 0.855395 0.029296 0.184560 11.00000 0.03705 0.07238 = 0.06160 0.00274 -0.00305 0.01242 AFIX 43 H3 2 0.975975 0.025962 0.209475 11.00000 -1.20000 AFIX 0 C4 1 0.760818 -0.075283 0.163254 11.00000 0.04951 0.05557 = 0.05983 0.00801 0.00611 0.01908 AFIX 43 H4 2 0.818448 -0.147543 0.174389 11.00000 -1.20000 AFIX 0 C5 1 0.583772 -0.072080 0.126072 11.00000 0.04716 0.04162 = 0.04613 0.00351 0.00929 0.00662 AFIX 43 H5 2 0.521526 -0.142136 0.111839 11.00000 -1.20000 AFIX 0 C6 1 0.495469 0.036759 0.109276 11.00000 0.03566 0.03887 = 0.03303 0.00130 0.00720 0.00390 C7 1 0.307450 0.044088 0.069277 11.00000 0.03657 0.03294 = 0.03585 0.00061 0.00771 0.00069 C8 1 0.236949 0.163071 0.057571 11.00000 0.03093 0.03403 = 0.04214 0.00121 0.00328 0.00094 C9 1 0.340979 0.257757 0.081738 11.00000 0.03192 0.03471 = 0.04147 0.00046 0.00444 0.00020 C10 1 0.277455 0.381453 0.079115 11.00000 0.03173 0.03072 = 0.04964 -0.00166 -0.00014 -0.00469 C11 1 0.228264 0.430288 0.152881 11.00000 0.04206 0.03629 = 0.05138 -0.00523 -0.00212 0.00029 C12 1 0.174512 0.546480 0.155672 11.00000 0.05877 0.04462 = 0.06679 -0.01389 -0.00573 0.00995 AFIX 43 H12 2 0.142777 0.577224 0.206046 11.00000 -1.20000 AFIX 0 C13 1 0.168917 0.615367 0.082865 11.00000 0.06456 0.03484 = 0.08530 -0.00788 -0.01863 0.00798 AFIX 43 H13 2 0.134967 0.694062 0.084397 11.00000 -1.20000 AFIX 0 C14 1 0.212223 0.570804 0.007975 11.00000 0.06048 0.04291 = 0.07269 0.01602 -0.01230 -0.00573 AFIX 43 H14 2 0.206049 0.618297 -0.041355 11.00000 -1.20000 AFIX 0 C15 1 0.265723 0.453476 0.006300 11.00000 0.04175 0.04098 = 0.05449 0.00367 -0.00023 -0.00693 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM OF7UOM_0m in P2(1)/n COLORLESS PRISM REM wR2 = 0.1058, GooF = S = 1.048, Restrained GooF = 1.048 for all data REM R1 = 0.0375 for 2348 Fo > 4sig(Fo) and 0.0511 for all 3023 data REM 182 parameters refined using 0 restraints END WGHT 0.0473 0.4019 REM Instructions for potential hydrogen bonds HTAB O3 O2 HTAB O3 O2_$1 REM Highest difference peak 0.330, deepest hole -0.319, 1-sigma level 0.043 Q1 1 0.1976 0.3982 0.2118 11.00000 0.05 0.33 Q2 1 0.2929 0.3199 0.0750 11.00000 0.05 0.18 Q3 1 0.5577 -0.0161 0.1010 11.00000 0.05 0.18 Q4 1 0.3776 0.3576 -0.1137 11.00000 0.05 0.18 Q5 1 0.5184 0.0819 0.1384 11.00000 0.05 0.18 Q6 1 0.1500 0.3005 0.2396 11.00000 0.05 0.18 Q7 1 0.2734 0.1034 0.0606 11.00000 0.05 0.17 Q8 1 0.4191 0.0370 0.0830 11.00000 0.05 0.17 ; _shelx_res_checksum 29942 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 Cl1 Cl 0.23403(8) 0.34277(5) 0.24500(3) 0.06325(18) Uani 1 1 d . . . . . Cl2 Cl 0.31804(8) 0.39710(6) -0.08919(4) 0.06893(19) Uani 1 1 d . . . . . O1 O 0.51771(14) 0.24933(10) 0.11744(8) 0.0425(3) Uani 1 1 d . . . . . O2 O 0.21166(16) -0.04276(10) 0.04758(8) 0.0460(3) Uani 1 1 d . . . . . O3 O 0.06344(15) 0.18070(10) 0.02394(10) 0.0538(4) Uani 1 1 d . . . . . H3A H 0.015067 0.117044 0.010127 0.081 Uiso 1 1 calc R U . . . C1 C 0.5931(2) 0.13958(15) 0.13128(10) 0.0383(4) Uani 1 1 d . . . . . C2 C 0.7732(2) 0.13727(18) 0.16931(13) 0.0516(5) Uani 1 1 d . . . . . H2 H 0.836249 0.206898 0.184029 0.062 Uiso 1 1 calc R U . . . C3 C 0.8554(3) 0.0293(2) 0.18456(13) 0.0587(5) Uani 1 1 d . . . . . H3 H 0.975975 0.025962 0.209475 0.070 Uiso 1 1 calc R U . . . C4 C 0.7608(3) -0.07528(19) 0.16325(13) 0.0555(5) Uani 1 1 d . . . . . H4 H 0.818448 -0.147543 0.174389 0.067 Uiso 1 1 calc R U . . . C5 C 0.5838(2) -0.07208(16) 0.12607(11) 0.0449(4) Uani 1 1 d . . . . . H5 H 0.521526 -0.142136 0.111839 0.054 Uiso 1 1 calc R U . . . C6 C 0.4955(2) 0.03676(14) 0.10928(10) 0.0358(3) Uani 1 1 d . . . . . C7 C 0.3075(2) 0.04409(13) 0.06928(10) 0.0350(3) Uani 1 1 d . . . . . C8 C 0.2369(2) 0.16307(14) 0.05757(11) 0.0362(3) Uani 1 1 d . . . . . C9 C 0.3410(2) 0.25776(14) 0.08174(10) 0.0364(3) Uani 1 1 d . . . . . C10 C 0.2775(2) 0.38145(14) 0.07911(11) 0.0384(4) Uani 1 1 d . . . . . C11 C 0.2283(2) 0.43029(15) 0.15288(12) 0.0447(4) Uani 1 1 d . . . . . C12 C 0.1745(3) 0.54648(17) 0.15567(14) 0.0591(5) Uani 1 1 d . . . . . H12 H 0.142777 0.577224 0.206046 0.071 Uiso 1 1 calc R U . . . C13 C 0.1689(3) 0.61537(18) 0.08286(16) 0.0659(6) Uani 1 1 d . . . . . H13 H 0.134967 0.694062 0.084397 0.079 Uiso 1 1 calc R U . . . C14 C 0.2122(3) 0.57080(18) 0.00797(15) 0.0620(6) Uani 1 1 d . . . . . H14 H 0.206049 0.618297 -0.041355 0.074 Uiso 1 1 calc R U . . . C15 C 0.2657(2) 0.45348(16) 0.00630(12) 0.0470(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 Cl1 0.0805(4) 0.0594(3) 0.0513(3) -0.0010(2) 0.0162(2) 0.0046(3) Cl2 0.0757(4) 0.0761(4) 0.0571(3) 0.0085(3) 0.0180(3) -0.0049(3) O1 0.0322(6) 0.0367(6) 0.0555(7) -0.0017(5) 0.0001(5) -0.0025(5) O2 0.0428(7) 0.0312(6) 0.0597(8) -0.0003(5) -0.0007(5) -0.0028(5) O3 0.0331(6) 0.0307(6) 0.0900(10) 0.0001(6) -0.0074(6) -0.0001(5) C1 0.0342(8) 0.0417(9) 0.0383(8) 0.0003(7) 0.0048(6) 0.0033(7) C2 0.0375(9) 0.0574(11) 0.0564(11) -0.0022(9) -0.0002(8) -0.0002(8) C3 0.0370(10) 0.0724(14) 0.0616(12) 0.0027(10) -0.0031(8) 0.0124(9) C4 0.0495(11) 0.0556(12) 0.0598(12) 0.0080(9) 0.0061(9) 0.0191(9) C5 0.0472(10) 0.0416(9) 0.0461(9) 0.0035(7) 0.0093(8) 0.0066(7) C6 0.0357(8) 0.0389(9) 0.0330(7) 0.0013(6) 0.0072(6) 0.0039(6) C7 0.0366(8) 0.0329(8) 0.0359(8) 0.0006(6) 0.0077(6) 0.0007(6) C8 0.0309(8) 0.0340(8) 0.0421(8) 0.0012(7) 0.0033(6) 0.0009(6) C9 0.0319(8) 0.0347(8) 0.0415(8) 0.0005(7) 0.0044(6) 0.0002(6) C10 0.0317(8) 0.0307(8) 0.0496(9) -0.0017(7) -0.0001(7) -0.0047(6) C11 0.0421(9) 0.0363(9) 0.0514(10) -0.0052(7) -0.0021(7) 0.0003(7) C12 0.0588(12) 0.0446(11) 0.0668(13) -0.0139(10) -0.0057(10) 0.0099(9) C13 0.0646(13) 0.0348(10) 0.0853(16) -0.0079(10) -0.0186(11) 0.0080(9) C14 0.0605(13) 0.0429(11) 0.0727(14) 0.0160(10) -0.0123(10) -0.0057(9) C15 0.0417(9) 0.0410(10) 0.0545(10) 0.0037(8) -0.0002(8) -0.0069(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' 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 C9 O1 C1 118.85(12) . . ? C8 O3 H3A 109.5 . . ? O1 C1 C6 122.10(14) . . ? O1 C1 C2 115.88(15) . . ? C6 C1 C2 122.02(16) . . ? C3 C2 C1 118.23(18) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 121.03(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.30(18) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.22(18) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 118.20(15) . . ? C1 C6 C7 119.83(14) . . ? C5 C6 C7 121.97(15) . . ? O2 C7 C8 121.30(14) . . ? O2 C7 C6 123.87(14) . . ? C8 C7 C6 114.82(14) . . ? O3 C8 C9 118.48(14) . . ? O3 C8 C7 120.15(14) . . ? C9 C8 C7 121.34(14) . . ? C8 C9 O1 123.04(14) . . ? C8 C9 C10 124.98(14) . . ? O1 C9 C10 111.84(13) . . ? C15 C10 C11 117.04(16) . . ? C15 C10 C9 123.37(16) . . ? C11 C10 C9 119.59(15) . . ? C12 C11 C10 122.33(18) . . ? C12 C11 Cl1 118.64(16) . . ? C10 C11 Cl1 119.03(13) . . ? C13 C12 C11 118.7(2) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C14 C13 C12 121.27(19) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.3(2) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C10 C15 C14 121.40(19) . . ? C10 C15 Cl2 119.58(14) . . ? C14 C15 Cl2 119.02(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 Cl1 C11 1.7344(19) . ? Cl2 C15 1.731(2) . ? O1 C9 1.3625(19) . ? O1 C1 1.370(2) . ? O2 C7 1.2343(19) . ? O3 C8 1.3446(19) . ? O3 H3A 0.8200 . ? C1 C6 1.390(2) . ? C1 C2 1.391(2) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.394(3) . ? C3 H3 0.9300 . ? C4 C5 1.367(3) . ? C4 H4 0.9300 . ? C5 C6 1.406(2) . ? C5 H5 0.9300 . ? C6 C7 1.455(2) . ? C7 C8 1.450(2) . ? C8 C9 1.345(2) . ? C9 C10 1.481(2) . ? C10 C15 1.383(2) . ? C10 C11 1.387(2) . ? C11 C12 1.382(3) . ? C12 C13 1.368(3) . ? C12 H12 0.9300 . ? C13 C14 1.366(3) . ? C13 H13 0.9300 . ? C14 C15 1.392(3) . ? C14 H14 0.9300 . ? 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 _geom_hbond_publ_flag O3 H3A O2 0.82 2.35 2.7690(17) 112.1 . yes O3 H3A O2 0.82 1.98 2.6846(16) 143.5 3 yes 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 C9 O1 C1 C6 0.6(2) . . . . ? C9 O1 C1 C2 -178.91(15) . . . . ? O1 C1 C2 C3 -179.95(17) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? O1 C1 C6 C5 -179.82(15) . . . . ? C2 C1 C6 C5 -0.3(2) . . . . ? O1 C1 C6 C7 0.7(2) . . . . ? C2 C1 C6 C7 -179.76(15) . . . . ? C4 C5 C6 C1 0.1(2) . . . . ? C4 C5 C6 C7 179.60(16) . . . . ? C1 C6 C7 O2 179.77(15) . . . . ? C5 C6 C7 O2 0.3(2) . . . . ? C1 C6 C7 C8 -1.3(2) . . . . ? C5 C6 C7 C8 179.28(15) . . . . ? O2 C7 C8 O3 1.2(2) . . . . ? C6 C7 C8 O3 -177.79(14) . . . . ? O2 C7 C8 C9 179.55(16) . . . . ? C6 C7 C8 C9 0.6(2) . . . . ? O3 C8 C9 O1 179.18(14) . . . . ? C7 C8 C9 O1 0.8(3) . . . . ? O3 C8 C9 C10 3.8(3) . . . . ? C7 C8 C9 C10 -174.64(15) . . . . ? C1 O1 C9 C8 -1.4(2) . . . . ? C1 O1 C9 C10 174.54(14) . . . . ? C8 C9 C10 C15 -88.7(2) . . . . ? O1 C9 C10 C15 95.46(18) . . . . ? C8 C9 C10 C11 92.1(2) . . . . ? O1 C9 C10 C11 -83.77(18) . . . . ? C15 C10 C11 C12 -1.8(3) . . . . ? C9 C10 C11 C12 177.45(16) . . . . ? C15 C10 C11 Cl1 178.12(12) . . . . ? C9 C10 C11 Cl1 -2.6(2) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? Cl1 C11 C12 C13 -179.62(15) . . . . ? C11 C12 C13 C14 1.1(3) . . . . ? C12 C13 C14 C15 -1.0(3) . . . . ? C11 C10 C15 C14 1.9(2) . . . . ? C9 C10 C15 C14 -177.30(17) . . . . ? C11 C10 C15 Cl2 -177.93(13) . . . . ? C9 C10 C15 Cl2 2.8(2) . . . . ? C13 C14 C15 C10 -0.6(3) . . . . ? C13 C14 C15 Cl2 179.29(16) . . . . ?