#------------------------------------------------------------------------------ #$Date: 2021-09-30 03:44:53 +0300 (Thu, 30 Sep 2021) $ #$Revision: 269388 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060975.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_7060975 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-(2,4-Dichlorophenyl)-3-hydroxy-4H-chromen-4-one ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 79.643(4) _cell_angle_beta 82.090(4) _cell_angle_gamma 79.560(3) _cell_formula_units_Z 2 _cell_length_a 6.4976(5) _cell_length_b 8.4557(7) _cell_length_c 12.4568(11) _cell_measurement_reflns_used 2486 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.500 _cell_measurement_theta_min 2.481 _cell_volume 658.19(10) _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 7.76 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _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 0.0261 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 10440 _diffrn_reflns_theta_full 27.234 _diffrn_reflns_theta_max 27.234 _diffrn_reflns_theta_min 2.481 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.496 _exptl_absorpt_correction_T_max 0.885 _exptl_absorpt_correction_T_min 0.825 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.207 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.045 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 2915 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0340 _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^)+(0.0465P)^2^+0.1662P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0910 _refine_ls_wR_factor_ref 0.0966 _reflns_number_gt 2486 _reflns_number_total 2915 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d1nj04340d2.cif _cod_data_source_block OF5 _cod_database_code 7060975 _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 OF5UOM_0m in P-1 COLORLESS ROD shelx.res created by SHELXL-2018/3 at 08:53:21 on 10-Aug-2021 CELL 0.71073 6.4976 8.4557 12.4568 79.643 82.090 79.560 ZERR 2.00 0.0005 0.0007 0.0011 0.004 0.004 0.003 LATT 1 SFAC C H O CL UNIT 30 16 6 4 MERG 2 OMIT 0 0 1 OMIT 1 0 1 FMAP 2 PLAN 6 SIZE 0.280 0.300 0.420 ACTA HTAB 2.00000 BOND $H CONF LIST 4 L.S. 40 TEMP 23.00 HTAB O3 O2 EQIV $1 -x+3, -y+1, -z HTAB O3 O2_$1 EQIV $2 -x+3, -y, -z+1 HTAB C12 Cl1_$2 WGHT 0.046500 0.166200 FVAR 0.28228 CL1 4 1.387618 0.243756 0.379547 11.00000 0.05877 0.05148 = 0.07421 0.00297 -0.02477 -0.01570 CL2 4 1.145987 -0.341694 0.453634 11.00000 0.10826 0.03444 = 0.08644 0.00748 0.02250 -0.00958 O1 3 0.846437 0.431561 0.242632 11.00000 0.03371 0.04012 = 0.04502 -0.00064 0.00418 -0.00309 O2 3 1.278826 0.623306 0.010815 11.00000 0.04160 0.04446 = 0.05884 0.00745 0.01135 -0.00475 O3 3 1.378639 0.311489 0.125006 11.00000 0.03838 0.03887 = 0.05967 0.00518 0.01131 0.00316 AFIX 147 H3A 2 1.452967 0.361829 0.077276 11.00000 -1.50000 AFIX 0 C1 1 0.797218 0.585807 0.188442 11.00000 0.03546 0.03781 = 0.03926 -0.00549 -0.00331 -0.00244 C2 1 0.595471 0.668961 0.214935 11.00000 0.03636 0.05649 = 0.05100 -0.00668 0.00250 -0.00042 AFIX 43 H2 2 0.499398 0.618606 0.265970 11.00000 -1.20000 AFIX 0 C3 1 0.541829 0.826473 0.164149 11.00000 0.04161 0.05817 = 0.05631 -0.01109 -0.00680 0.01202 AFIX 43 H3 2 0.408030 0.883013 0.181280 11.00000 -1.20000 AFIX 0 C4 1 0.684291 0.903168 0.087378 11.00000 0.05187 0.04239 = 0.05278 -0.00488 -0.01517 0.00720 AFIX 43 H4 2 0.646683 1.010798 0.055042 11.00000 -1.20000 AFIX 0 C5 1 0.880071 0.819342 0.059714 11.00000 0.04630 0.03761 = 0.04466 -0.00208 -0.00642 -0.00352 AFIX 43 H5 2 0.973352 0.869411 0.006709 11.00000 -1.20000 AFIX 0 C6 1 0.940959 0.658701 0.110651 11.00000 0.03549 0.03513 = 0.03728 -0.00550 -0.00425 -0.00342 C7 1 1.148535 0.567996 0.082850 11.00000 0.03496 0.03532 = 0.03947 -0.00381 -0.00007 -0.00610 C8 1 1.191063 0.406537 0.145117 11.00000 0.03405 0.03512 = 0.04056 -0.00361 0.00077 -0.00242 C9 1 1.043409 0.345985 0.221214 11.00000 0.03472 0.03481 = 0.03892 -0.00479 -0.00141 -0.00400 C10 1 1.066538 0.179931 0.283743 11.00000 0.04029 0.03405 = 0.03782 -0.00430 0.00378 -0.00628 C11 1 1.222454 0.118810 0.353517 11.00000 0.04322 0.03535 = 0.04296 -0.00244 0.00044 -0.00617 C12 1 1.246970 -0.041147 0.406738 11.00000 0.05555 0.03891 = 0.04562 0.00161 0.00002 -0.00057 AFIX 43 H12 2 1.352954 -0.080918 0.452330 11.00000 -1.20000 AFIX 0 C13 1 1.110588 -0.139874 0.390505 11.00000 0.06783 0.03159 = 0.04699 -0.00243 0.01564 -0.00764 C14 1 0.949920 -0.082548 0.325661 11.00000 0.06671 0.04594 = 0.05453 -0.00948 0.00744 -0.02501 AFIX 43 H14 2 0.856724 -0.149989 0.317537 11.00000 -1.20000 AFIX 0 C15 1 0.928715 0.077286 0.272510 11.00000 0.05110 0.04783 = 0.04894 -0.00698 -0.00180 -0.01546 AFIX 43 H15 2 0.820201 0.116711 0.228459 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM OF5UOM_0m in P-1 COLORLESS ROD REM wR2 = 0.0966, GooF = S = 1.041, Restrained GooF = 1.041 for all data REM R1 = 0.0340 for 2486 Fo > 4sig(Fo) and 0.0401 for all 2915 data REM 182 parameters refined using 0 restraints END WGHT 0.0465 0.1662 REM Instructions for potential hydrogen bonds HTAB O3 O2 HTAB O3 O2_$1 HTAB C12 Cl1_$2 REM Highest difference peak 0.207, deepest hole -0.282, 1-sigma level 0.045 Q1 1 0.8657 0.6221 0.1440 11.00000 0.05 0.21 Q2 1 1.1232 -0.3675 0.3912 11.00000 0.05 0.21 Q3 1 1.1721 0.1468 0.3024 11.00000 0.05 0.18 Q4 1 1.1386 0.3848 0.2021 11.00000 0.05 0.17 Q5 1 1.0343 0.6161 0.0934 11.00000 0.05 0.17 Q6 1 1.2697 0.0293 0.3657 11.00000 0.05 0.17 ; _shelx_res_checksum 43789 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 1.38762(7) 0.24376(5) 0.37955(4) 0.06056(15) Uani 1 1 d . . . . . Cl2 Cl 1.14599(10) -0.34169(5) 0.45363(5) 0.0820(2) Uani 1 1 d . . . . . O1 O 0.84644(15) 0.43156(12) 0.24263(8) 0.0416(2) Uani 1 1 d . . . . . O2 O 1.27883(16) 0.62331(13) 0.01082(9) 0.0522(3) Uani 1 1 d . . . . . O3 O 1.37864(16) 0.31149(13) 0.12501(10) 0.0501(3) Uani 1 1 d . . . . . H3A H 1.452967 0.361829 0.077276 0.075 Uiso 1 1 calc R U . . . C1 C 0.7972(2) 0.58581(17) 0.18844(11) 0.0381(3) Uani 1 1 d . . . . . C2 C 0.5955(2) 0.6690(2) 0.21494(14) 0.0498(4) Uani 1 1 d . . . . . H2 H 0.499398 0.618606 0.265970 0.060 Uiso 1 1 calc R U . . . C3 C 0.5418(3) 0.8265(2) 0.16415(14) 0.0542(4) Uani 1 1 d . . . . . H3 H 0.408030 0.883013 0.181280 0.065 Uiso 1 1 calc R U . . . C4 C 0.6843(3) 0.9032(2) 0.08738(14) 0.0503(4) Uani 1 1 d . . . . . H4 H 0.646683 1.010798 0.055042 0.060 Uiso 1 1 calc R U . . . C5 C 0.8801(2) 0.81934(18) 0.05971(13) 0.0437(3) Uani 1 1 d . . . . . H5 H 0.973352 0.869411 0.006709 0.052 Uiso 1 1 calc R U . . . C6 C 0.9410(2) 0.65870(17) 0.11065(11) 0.0363(3) Uani 1 1 d . . . . . C7 C 1.1485(2) 0.56800(17) 0.08285(11) 0.0372(3) Uani 1 1 d . . . . . C8 C 1.1911(2) 0.40654(17) 0.14512(11) 0.0377(3) Uani 1 1 d . . . . . C9 C 1.0434(2) 0.34598(17) 0.22121(11) 0.0367(3) Uani 1 1 d . . . . . C10 C 1.0665(2) 0.17993(17) 0.28374(11) 0.0383(3) Uani 1 1 d . . . . . C11 C 1.2225(2) 0.11881(18) 0.35352(12) 0.0415(3) Uani 1 1 d . . . . . C12 C 1.2470(3) -0.04115(19) 0.40674(13) 0.0492(4) Uani 1 1 d . . . . . H12 H 1.352954 -0.080918 0.452330 0.059 Uiso 1 1 calc R U . . . C13 C 1.1106(3) -0.13987(18) 0.39050(13) 0.0514(4) Uani 1 1 d . . . . . C14 C 0.9499(3) -0.0825(2) 0.32566(14) 0.0549(4) Uani 1 1 d . . . . . H14 H 0.856724 -0.149989 0.317537 0.066 Uiso 1 1 calc R U . . . C15 C 0.9287(3) 0.0773(2) 0.27251(13) 0.0488(4) Uani 1 1 d . . . . . H15 H 0.820201 0.116711 0.228459 0.059 Uiso 1 1 calc R U . . . 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 0.0588(3) 0.0515(3) 0.0742(3) 0.0030(2) -0.0248(2) -0.01570(19) Cl2 0.1083(4) 0.0344(2) 0.0864(4) 0.0075(2) 0.0225(3) -0.0096(2) O1 0.0337(5) 0.0401(5) 0.0450(5) -0.0006(4) 0.0042(4) -0.0031(4) O2 0.0416(6) 0.0445(6) 0.0588(7) 0.0075(5) 0.0113(5) -0.0048(5) O3 0.0384(5) 0.0389(6) 0.0597(7) 0.0052(5) 0.0113(5) 0.0032(4) C1 0.0355(7) 0.0378(7) 0.0393(7) -0.0055(6) -0.0033(5) -0.0024(5) C2 0.0364(7) 0.0565(10) 0.0510(9) -0.0067(7) 0.0025(6) -0.0004(7) C3 0.0416(8) 0.0582(10) 0.0563(9) -0.0111(8) -0.0068(7) 0.0120(7) C4 0.0519(9) 0.0424(8) 0.0528(9) -0.0049(7) -0.0152(7) 0.0072(7) C5 0.0463(8) 0.0376(8) 0.0447(8) -0.0021(6) -0.0064(6) -0.0035(6) C6 0.0355(7) 0.0351(7) 0.0373(7) -0.0055(5) -0.0042(5) -0.0034(5) C7 0.0350(7) 0.0353(7) 0.0395(7) -0.0038(6) -0.0001(5) -0.0061(5) C8 0.0340(7) 0.0351(7) 0.0406(7) -0.0036(6) 0.0008(5) -0.0024(5) C9 0.0347(7) 0.0348(7) 0.0389(7) -0.0048(5) -0.0014(5) -0.0040(5) C10 0.0403(7) 0.0341(7) 0.0378(7) -0.0043(5) 0.0038(5) -0.0063(5) C11 0.0432(7) 0.0354(7) 0.0430(7) -0.0024(6) 0.0004(6) -0.0062(6) C12 0.0556(9) 0.0389(8) 0.0456(8) 0.0016(6) 0.0000(7) -0.0006(7) C13 0.0678(10) 0.0316(7) 0.0470(8) -0.0024(6) 0.0156(7) -0.0076(7) C14 0.0667(10) 0.0459(9) 0.0545(9) -0.0095(7) 0.0074(8) -0.0250(8) C15 0.0511(9) 0.0478(9) 0.0489(8) -0.0070(7) -0.0018(7) -0.0155(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 C1 O1 C9 119.28(11) . . ? C8 O3 H3A 109.5 . . ? O1 C1 C6 121.83(12) . . ? O1 C1 C2 116.98(13) . . ? C6 C1 C2 121.19(14) . . ? C3 C2 C1 118.70(15) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 121.19(14) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.75(15) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.60(14) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 118.53(13) . . ? C1 C6 C7 120.05(12) . . ? C5 C6 C7 121.42(13) . . ? O2 C7 C8 122.02(13) . . ? O2 C7 C6 122.98(13) . . ? C8 C7 C6 115.00(12) . . ? O3 C8 C9 119.10(12) . . ? O3 C8 C7 119.74(12) . . ? C9 C8 C7 121.12(12) . . ? C8 C9 O1 122.65(12) . . ? C8 C9 C10 125.23(12) . . ? O1 C9 C10 111.97(11) . . ? C15 C10 C11 117.85(14) . . ? C15 C10 C9 119.08(13) . . ? C11 C10 C9 123.07(13) . . ? C12 C11 C10 121.60(14) . . ? C12 C11 Cl1 117.88(12) . . ? C10 C11 Cl1 120.50(11) . . ? C13 C12 C11 118.47(15) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C14 C13 C12 121.71(15) . . ? C14 C13 Cl2 119.75(14) . . ? C12 C13 Cl2 118.54(14) . . ? C13 C14 C15 119.01(15) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C14 C15 C10 121.29(16) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? 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 Cl1 C11 1.7329(16) . ? Cl2 C13 1.7345(16) . ? O1 C1 1.3604(17) . ? O1 C9 1.3684(16) . ? O2 C7 1.2346(17) . ? O3 C8 1.3519(16) . ? O3 H3A 0.8200 . ? C1 C6 1.3914(19) . ? C1 C2 1.397(2) . ? C2 C3 1.373(2) . ? C2 H2 0.9300 . ? C3 C4 1.394(2) . ? C3 H3 0.9300 . ? C4 C5 1.371(2) . ? C4 H4 0.9300 . ? C5 C6 1.403(2) . ? C5 H5 0.9300 . ? C6 C7 1.4558(19) . ? C7 C8 1.4434(19) . ? C8 C9 1.3544(19) . ? C9 C10 1.4708(19) . ? C10 C15 1.391(2) . ? C10 C11 1.393(2) . ? C11 C12 1.387(2) . ? C12 C13 1.379(2) . ? C12 H12 0.9300 . ? C13 C14 1.373(3) . ? C14 C15 1.386(2) . ? C14 H14 0.9300 . ? C15 H15 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 2.36 2.7715(15) 112.2 . yes O3 H3A O2 0.82 1.94 2.6820(14) 150.2 2_865 yes C12 H12 Cl1 0.93 2.87 3.7796(17) 167.4 2_856 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 0.8(2) . . . . ? C9 O1 C1 C2 -178.76(13) . . . . ? O1 C1 C2 C3 178.26(14) . . . . ? C6 C1 C2 C3 -1.3(2) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 1.6(3) . . . . ? C3 C4 C5 C6 -2.1(2) . . . . ? O1 C1 C6 C5 -178.78(13) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? O1 C1 C6 C7 1.8(2) . . . . ? C2 C1 C6 C7 -178.64(14) . . . . ? C4 C5 C6 C1 1.0(2) . . . . ? C4 C5 C6 C7 -179.65(14) . . . . ? C1 C6 C7 O2 176.39(14) . . . . ? C5 C6 C7 O2 -3.0(2) . . . . ? C1 C6 C7 C8 -2.9(2) . . . . ? C5 C6 C7 C8 177.71(13) . . . . ? O2 C7 C8 O3 0.1(2) . . . . ? C6 C7 C8 O3 179.39(13) . . . . ? O2 C7 C8 C9 -177.72(15) . . . . ? C6 C7 C8 C9 1.6(2) . . . . ? O3 C8 C9 O1 -176.86(13) . . . . ? C7 C8 C9 O1 0.9(2) . . . . ? O3 C8 C9 C10 -1.8(2) . . . . ? C7 C8 C9 C10 175.96(13) . . . . ? C1 O1 C9 C8 -2.2(2) . . . . ? C1 O1 C9 C10 -177.83(12) . . . . ? C8 C9 C10 C15 -118.58(17) . . . . ? O1 C9 C10 C15 56.90(18) . . . . ? C8 C9 C10 C11 60.7(2) . . . . ? O1 C9 C10 C11 -123.82(14) . . . . ? C15 C10 C11 C12 2.8(2) . . . . ? C9 C10 C11 C12 -176.48(13) . . . . ? C15 C10 C11 Cl1 -175.24(11) . . . . ? C9 C10 C11 Cl1 5.5(2) . . . . ? C10 C11 C12 C13 -0.9(2) . . . . ? Cl1 C11 C12 C13 177.20(12) . . . . ? C11 C12 C13 C14 -1.6(2) . . . . ? C11 C12 C13 Cl2 178.05(11) . . . . ? C12 C13 C14 C15 2.1(2) . . . . ? Cl2 C13 C14 C15 -177.58(12) . . . . ? C13 C14 C15 C10 0.0(2) . . . . ? C11 C10 C15 C14 -2.3(2) . . . . ? C9 C10 C15 C14 176.99(14) . . . . ?