#------------------------------------------------------------------------------ #$Date: 2021-09-30 03:44:53 +0300 (Thu, 30 Sep 2021) $ #$Revision: 269388 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060976.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_7060976 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-(2,3-Dichlorophenyl)-3-hydroxy-4H-chromen-4-one ; _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 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 93.993(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3596(5) _cell_length_b 14.1923(7) _cell_length_c 8.1555(4) _cell_measurement_reflns_used 2389 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.535 _cell_measurement_theta_min 2.300 _cell_volume 1311.63(11) _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 0.993 _diffrn_measured_fraction_theta_max 0.993 _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 0.0214 _diffrn_reflns_av_unetI/netI 0.0208 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 10900 _diffrn_reflns_theta_full 27.535 _diffrn_reflns_theta_max 27.535 _diffrn_reflns_theta_min 2.870 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.497 _exptl_absorpt_correction_T_max 0.870 _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2005)' _exptl_crystal_colour 'light orange' _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.296 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.042 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3012 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0514P)^2^+0.4899P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1026 _refine_ls_wR_factor_ref 0.1107 _reflns_number_gt 2389 _reflns_number_total 3012 _reflns_threshold_expression I>2\s(I) _cod_data_source_file d1nj04340d2.cif _cod_data_source_block OF6 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7060976 _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 OF6 in P2(1)/c LIGHT ORANGE PRISM shelx.res created by SHELXL-2018/3 at 08:55:30 on 10-Aug-2021 CELL 0.71073 11.3596 14.1923 8.1555 90.000 93.993 90.000 ZERR 4.00 0.0005 0.0007 0.0004 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H O Cl UNIT 60 32 12 8 L.S. 40 ACTA BOND $H FMAP 2 PLAN 10 SIZE 0.40 0.32 0.30 CONF HTAB OMIT 1 1 0 TEMP 23.000 EQIV $1 -x, -y+1, -z+1 HTAB O3 O2_$1 EQIV $2 -x+1, -y+1, -z+1 HTAB C13 O3_$2 WGHT 0.048700 0.455300 FVAR 0.23366 CL1 4 0.349932 0.732248 0.435423 11.00000 0.06044 0.06301 = 0.08252 -0.02105 -0.00567 0.00216 CL2 4 0.620053 0.708514 0.517810 11.00000 0.06750 0.12718 = 0.10496 0.01774 -0.03836 -0.03634 O1 3 0.211285 0.606165 0.047976 11.00000 0.03847 0.05439 = 0.03581 0.00562 0.00250 -0.00369 O2 3 -0.055404 0.572582 0.351086 11.00000 0.03531 0.07838 = 0.05501 0.01652 0.00834 0.00269 O3 3 0.175692 0.550106 0.471210 11.00000 0.03607 0.09969 = 0.03976 0.02120 0.00099 -0.00300 AFIX 147 H3A 2 0.121566 0.520290 0.507924 11.00000 -1.50000 AFIX 0 C1 1 0.097276 0.620987 -0.012008 11.00000 0.04329 0.03879 = 0.03922 0.00187 -0.00512 -0.00517 C2 1 0.080814 0.644764 -0.177882 11.00000 0.05988 0.05726 = 0.03896 0.00575 -0.00245 -0.01014 AFIX 43 H2 2 0.144726 0.649685 -0.242703 11.00000 -1.20000 AFIX 0 C3 1 -0.032018 0.660721 -0.243101 11.00000 0.07346 0.05380 = 0.04546 0.00735 -0.01872 -0.00625 AFIX 43 H3 2 -0.044647 0.676353 -0.353668 11.00000 -1.20000 AFIX 0 C4 1 -0.127445 0.653911 -0.146829 11.00000 0.05427 0.05622 = 0.06107 0.00597 -0.02099 -0.00010 AFIX 43 H4 2 -0.203149 0.665802 -0.193036 11.00000 -1.20000 AFIX 0 C5 1 -0.111283 0.629845 0.015639 11.00000 0.04118 0.04953 = 0.05589 0.00165 -0.00798 0.00052 AFIX 43 H5 2 -0.175859 0.625031 0.079248 11.00000 -1.20000 AFIX 0 C6 1 0.003071 0.612405 0.086288 11.00000 0.03878 0.03545 = 0.04160 0.00147 -0.00494 -0.00252 C7 1 0.024148 0.584874 0.257347 11.00000 0.03542 0.04163 = 0.04316 0.00352 0.00102 0.00006 C8 1 0.146896 0.572412 0.312308 11.00000 0.03512 0.05095 = 0.03632 0.00605 0.00008 -0.00036 C9 1 0.233650 0.584353 0.210249 11.00000 0.03593 0.04103 = 0.03628 0.00221 0.00049 -0.00109 C10 1 0.361859 0.573709 0.254710 11.00000 0.03450 0.04737 = 0.03817 0.00932 0.00587 0.00356 C11 1 0.422930 0.638220 0.356610 11.00000 0.03559 0.05493 = 0.04434 0.00875 0.00006 0.00046 C12 1 0.543145 0.627772 0.392930 11.00000 0.03733 0.08000 = 0.05565 0.02254 -0.00612 -0.00518 C13 1 0.602136 0.552483 0.330239 11.00000 0.03575 0.11020 = 0.07759 0.03602 0.00494 0.01748 AFIX 43 H13 2 0.682755 0.545302 0.355355 11.00000 -1.20000 AFIX 0 C14 1 0.542226 0.488457 0.231283 11.00000 0.06234 0.08797 = 0.08060 0.01496 0.02200 0.03606 AFIX 43 H14 2 0.582279 0.437529 0.189872 11.00000 -1.20000 AFIX 0 C15 1 0.422496 0.498666 0.192082 11.00000 0.05626 0.06250 = 0.05707 0.00060 0.01300 0.01243 AFIX 43 H15 2 0.382626 0.455077 0.123558 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM OF6 in P2(1)/c LIGHT ORANGE PRISM REM wR2 = 0.1107, GooF = S = 1.040, Restrained GooF = 1.040 for all data REM R1 = 0.0408 for 2389 Fo > 4sig(Fo) and 0.0533 for all 3012 data REM 182 parameters refined using 0 restraints END WGHT 0.0487 0.4553 REM Instructions for potential hydrogen bonds HTAB O3 O2_$1 HTAB C13 O3_$2 REM Highest difference peak 0.296, deepest hole -0.468, 1-sigma level 0.042 Q1 1 0.6554 0.6735 0.4391 11.00000 0.05 0.30 Q2 1 0.3015 0.5821 0.2397 11.00000 0.05 0.25 Q3 1 0.4000 0.7176 0.3638 11.00000 0.05 0.17 Q4 1 0.0113 0.6005 0.1655 11.00000 0.05 0.17 Q5 1 -0.0486 0.6212 0.0511 11.00000 0.05 0.16 Q6 1 0.0468 0.6363 0.0504 11.00000 0.05 0.16 Q7 1 0.3319 0.7420 0.3169 11.00000 0.05 0.15 Q8 1 0.3792 0.5345 0.2534 11.00000 0.05 0.14 Q9 1 0.1914 0.6035 0.2752 11.00000 0.05 0.14 Q10 1 0.4896 0.6473 0.3578 11.00000 0.05 0.14 ; _shelx_res_checksum 94683 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 0.34993(5) 0.73225(4) 0.43542(8) 0.0692(2) Uani 1 1 d . . . . . Cl2 Cl 0.62005(6) 0.70851(6) 0.51781(10) 0.1020(3) Uani 1 1 d . . . . . O1 O 0.21129(10) 0.60617(9) 0.04798(13) 0.0429(3) Uani 1 1 d . . . . . O2 O -0.05540(10) 0.57258(11) 0.35109(16) 0.0560(4) Uani 1 1 d . . . . . O3 O 0.17569(10) 0.55011(12) 0.47121(15) 0.0586(4) Uani 1 1 d . . . . . H3A H 0.121566 0.520290 0.507924 0.088 Uiso 1 1 calc R U . . . C1 C 0.09728(15) 0.62099(12) -0.0120(2) 0.0408(4) Uani 1 1 d . . . . . C2 C 0.08081(18) 0.64476(14) -0.1779(2) 0.0523(5) Uani 1 1 d . . . . . H2 H 0.144726 0.649685 -0.242703 0.063 Uiso 1 1 calc R U . . . C3 C -0.03202(19) 0.66072(14) -0.2431(2) 0.0586(5) Uani 1 1 d . . . . . H3 H -0.044647 0.676353 -0.353668 0.070 Uiso 1 1 calc R U . . . C4 C -0.12744(18) 0.65391(15) -0.1468(3) 0.0584(5) Uani 1 1 d . . . . . H4 H -0.203149 0.665802 -0.193036 0.070 Uiso 1 1 calc R U . . . C5 C -0.11128(16) 0.62985(13) 0.0156(2) 0.0494(4) Uani 1 1 d . . . . . H5 H -0.175859 0.625031 0.079248 0.059 Uiso 1 1 calc R U . . . C6 C 0.00307(14) 0.61241(12) 0.0863(2) 0.0390(4) Uani 1 1 d . . . . . C7 C 0.02415(14) 0.58487(12) 0.2573(2) 0.0401(4) Uani 1 1 d . . . . . C8 C 0.14690(14) 0.57241(13) 0.31231(19) 0.0409(4) Uani 1 1 d . . . . . C9 C 0.23365(14) 0.58435(12) 0.21025(19) 0.0378(4) Uani 1 1 d . . . . . C10 C 0.36186(14) 0.57371(12) 0.2547(2) 0.0399(4) Uani 1 1 d . . . . . C11 C 0.42293(15) 0.63822(13) 0.3566(2) 0.0451(4) Uani 1 1 d . . . . . C12 C 0.54315(16) 0.62777(17) 0.3929(2) 0.0581(5) Uani 1 1 d . . . . . C13 C 0.60214(18) 0.5525(2) 0.3302(3) 0.0745(7) Uani 1 1 d . . . . . H13 H 0.682755 0.545302 0.355355 0.089 Uiso 1 1 calc R U . . . C14 C 0.5422(2) 0.4885(2) 0.2313(3) 0.0762(7) Uani 1 1 d . . . . . H14 H 0.582279 0.437529 0.189872 0.091 Uiso 1 1 calc R U . . . C15 C 0.42250(19) 0.49867(15) 0.1921(3) 0.0582(5) Uani 1 1 d . . . . . H15 H 0.382626 0.455077 0.123558 0.070 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 0.0604(3) 0.0630(3) 0.0825(4) -0.0211(3) -0.0057(3) 0.0022(2) Cl2 0.0675(4) 0.1272(6) 0.1050(5) 0.0177(4) -0.0384(4) -0.0363(4) O1 0.0385(6) 0.0544(7) 0.0358(6) 0.0056(5) 0.0025(5) -0.0037(5) O2 0.0353(6) 0.0784(10) 0.0550(7) 0.0165(7) 0.0083(6) 0.0027(6) O3 0.0361(6) 0.0997(12) 0.0398(6) 0.0212(7) 0.0010(5) -0.0030(7) C1 0.0433(9) 0.0388(9) 0.0392(8) 0.0019(7) -0.0051(7) -0.0052(7) C2 0.0599(11) 0.0573(11) 0.0390(9) 0.0057(8) -0.0025(8) -0.0101(9) C3 0.0735(13) 0.0538(11) 0.0455(10) 0.0074(9) -0.0187(9) -0.0062(10) C4 0.0543(11) 0.0562(12) 0.0611(12) 0.0060(10) -0.0210(9) -0.0001(9) C5 0.0412(9) 0.0495(10) 0.0559(10) 0.0016(8) -0.0080(8) 0.0005(8) C6 0.0388(8) 0.0354(8) 0.0416(8) 0.0015(7) -0.0049(7) -0.0025(7) C7 0.0354(8) 0.0416(9) 0.0432(9) 0.0035(7) 0.0010(7) 0.0001(7) C8 0.0351(8) 0.0510(10) 0.0363(8) 0.0060(7) 0.0001(6) -0.0004(7) C9 0.0359(8) 0.0410(9) 0.0363(8) 0.0022(6) 0.0005(6) -0.0011(7) C10 0.0345(8) 0.0474(9) 0.0382(8) 0.0093(7) 0.0059(6) 0.0036(7) C11 0.0356(8) 0.0549(11) 0.0443(9) 0.0087(8) 0.0001(7) 0.0005(8) C12 0.0373(9) 0.0800(15) 0.0556(11) 0.0225(10) -0.0061(8) -0.0052(9) C13 0.0358(10) 0.110(2) 0.0776(15) 0.0360(15) 0.0049(10) 0.0175(12) C14 0.0623(14) 0.0880(18) 0.0806(16) 0.0150(14) 0.0220(12) 0.0361(13) C15 0.0563(12) 0.0625(13) 0.0571(11) 0.0006(9) 0.0130(9) 0.0124(10) 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 119.26(12) . . ? C8 O3 H3A 109.5 . . ? O1 C1 C6 121.95(14) . . ? O1 C1 C2 116.34(15) . . ? C6 C1 C2 121.71(16) . . ? C3 C2 C1 118.34(18) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 121.03(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.58(18) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.91(18) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 118.42(16) . . ? C1 C6 C7 119.79(14) . . ? C5 C6 C7 121.79(16) . . ? O2 C7 C8 121.46(15) . . ? O2 C7 C6 123.59(15) . . ? C8 C7 C6 114.94(14) . . ? C9 C8 O3 118.96(14) . . ? C9 C8 C7 121.70(15) . . ? O3 C8 C7 119.32(14) . . ? C8 C9 O1 122.26(14) . . ? C8 C9 C10 125.82(14) . . ? O1 C9 C10 111.91(13) . . ? C15 C10 C11 119.14(16) . . ? C15 C10 C9 119.54(17) . . ? C11 C10 C9 121.32(15) . . ? C12 C11 C10 120.08(18) . . ? C12 C11 Cl1 119.81(16) . . ? C10 C11 Cl1 120.10(13) . . ? C13 C12 C11 120.1(2) . . ? C13 C12 Cl2 119.57(16) . . ? C11 C12 Cl2 120.35(18) . . ? C14 C13 C12 120.00(19) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.1(2) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? 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 1.719(2) . ? Cl2 C12 1.729(2) . ? O1 C9 1.3656(19) . ? O1 C1 1.3684(19) . ? O2 C7 1.236(2) . ? O3 C8 1.3519(19) . ? O3 H3A 0.8200 . ? C1 C6 1.386(2) . ? C1 C2 1.394(2) . ? C2 C3 1.372(3) . ? C2 H2 0.9300 . ? C3 C4 1.385(3) . ? C3 H3 0.9300 . ? C4 C5 1.368(3) . ? C4 H4 0.9300 . ? C5 C6 1.406(2) . ? C5 H5 0.9300 . ? C6 C7 1.452(2) . ? C7 C8 1.445(2) . ? C8 C9 1.344(2) . ? C9 C10 1.484(2) . ? C10 C15 1.385(3) . ? C10 C11 1.389(3) . ? C11 C12 1.385(2) . ? C12 C13 1.378(4) . ? C13 C14 1.365(4) . ? C13 H13 0.9300 . ? C14 C15 1.383(3) . ? 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 1.94 2.6973(18) 154.2 3_566 yes C13 H13 O3 0.93 2.47 3.247(2) 141.1 3_666 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 -1.5(2) . . . . ? C9 O1 C1 C2 178.80(15) . . . . ? O1 C1 C2 C3 -179.69(17) . . . . ? C6 C1 C2 C3 0.6(3) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? O1 C1 C6 C5 179.30(16) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? O1 C1 C6 C7 -1.4(2) . . . . ? C2 C1 C6 C7 178.25(17) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C4 C5 C6 C7 -178.77(17) . . . . ? C1 C6 C7 O2 -177.41(17) . . . . ? C5 C6 C7 O2 1.9(3) . . . . ? C1 C6 C7 C8 2.6(2) . . . . ? C5 C6 C7 C8 -178.18(16) . . . . ? O2 C7 C8 C9 179.02(17) . . . . ? C6 C7 C8 C9 -1.0(3) . . . . ? O2 C7 C8 O3 -2.4(3) . . . . ? C6 C7 C8 O3 177.64(16) . . . . ? O3 C8 C9 O1 179.45(16) . . . . ? C7 C8 C9 O1 -2.0(3) . . . . ? O3 C8 C9 C10 1.1(3) . . . . ? C7 C8 C9 C10 179.70(16) . . . . ? C1 O1 C9 C8 3.2(2) . . . . ? C1 O1 C9 C10 -178.20(14) . . . . ? C8 C9 C10 C15 110.6(2) . . . . ? O1 C9 C10 C15 -67.9(2) . . . . ? C8 C9 C10 C11 -70.2(2) . . . . ? O1 C9 C10 C11 111.29(17) . . . . ? C15 C10 C11 C12 0.8(3) . . . . ? C9 C10 C11 C12 -178.47(16) . . . . ? C15 C10 C11 Cl1 179.76(14) . . . . ? C9 C10 C11 Cl1 0.5(2) . . . . ? C10 C11 C12 C13 -1.1(3) . . . . ? Cl1 C11 C12 C13 179.94(16) . . . . ? C10 C11 C12 Cl2 179.28(13) . . . . ? Cl1 C11 C12 Cl2 0.3(2) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? Cl2 C12 C13 C14 -179.88(18) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C10 -0.7(3) . . . . ? C11 C10 C15 C14 0.1(3) . . . . ? C9 C10 C15 C14 179.37(18) . . . . ?