#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:10:02 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257956 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240426.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_7240426 loop_ _publ_author_name 'Hulushe, Siya T.' 'Manyeruke, Meloddy H.' 'Louzada, Marcel' 'Rigin, Sergei' 'Hosten, Eric C.' 'Watkins, Gareth M.' _publ_section_title ; Exploring intermolecular contacts in multi-substituted benzaldehyde derivatives: X-ray, Hirshfeld surface and lattice energy analyses ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 16861 _journal_page_last 16874 _journal_paper_doi 10.1039/C9RA10752E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C14 H11 Cl O2' _chemical_formula_sum 'C14 H11 Cl O2' _chemical_formula_weight 246.68 _chemical_melting_point 342 _chemical_name_common 2-(benzyloxy)-5-chlorobenzaldehyde _chemical_name_systematic 5-chloro-2-(phenylmethoxy)benzaldehyde _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-02-22 deposited with the CCDC. 2020-04-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.171(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.9219(2) _cell_length_b 16.3089(6) _cell_length_c 14.7245(5) _cell_measurement_reflns_used 9688 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 28.31 _cell_measurement_theta_min 2.50 _cell_volume 1166.84(8) _computing_cell_refinement 'APEX2 v2011.4-1 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service v2011.4.0.0' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 2012)' _computing_publication_material 'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (H\"ubschle, 2011)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 200(2) _diffrn_detector_area_resol_mean 8.3333 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_unetI/netI 0.0183 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 24526 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.341 _diffrn_reflns_theta_min 1.877 _exptl_absorpt_coefficient_mu 0.312 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9274 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_crystal_colour 'pale brown' _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_description blocks _exptl_crystal_F_000 512 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane' _exptl_crystal_size_max 0.495 _exptl_crystal_size_mid 0.133 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.324 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2917 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0398P)^2^+0.3701P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0824 _refine_ls_wR_factor_ref 0.0880 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2378 _reflns_number_total 2917 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10752e2.cif _cod_data_source_block ia354 _cod_depositor_comments 'Adding full bibliography for 7240424--7240429.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240426 _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_estimated_absorpt_t_min 0.861 _shelx_estimated_absorpt_t_max 0.969 _shelx_res_file ; TITL ia354_a.res in P2(1)/n ia354.res created by SHELXL-2018/3 at 15:13:56 on 18-Feb-2019 REM Old TITL ia354_p_P21n in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.149, Rweak 0.006, Alpha 0.017 REM 0.281 for 99 systematic absences, Orientation as input REM Formula found by SHELXT: C14 O2 Cl CELL 0.71073 4.9219 16.3089 14.7245 90.000 99.171 90.000 ZERR 4.000 0.0002 0.0006 0.0005 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H O Cl UNIT 56 44 8 4 HTAB C1 O2 HTAB C22 O2 ACTA BOND $H CONF FMAP 2 HTAB L.S. 100 LIST 4 PLAN -20 SIZE 0.10 0.133 0.495 TEMP -73.160 REM WGHT 0.039800 0.370100 REM WGHT 0.039800 0.370100 REM WGHT 0.039800 0.370100 WGHT 0.039800 0.370100 FVAR 0.16556 CL1 4 -0.286961 0.075552 0.503252 11.00000 0.04216 0.03467 = 0.04519 -0.00334 0.00595 -0.01471 O1 3 0.415666 0.251232 0.343284 11.00000 0.05695 0.05553 = 0.02892 -0.01038 0.01806 -0.01297 O2 3 0.463278 0.353699 0.590460 11.00000 0.03758 0.03516 = 0.02338 -0.00640 0.00718 -0.01300 C1 1 0.428107 0.281077 0.418742 11.00000 0.03666 0.03804 = 0.03071 -0.00489 0.01219 -0.00740 AFIX 43 H1 2 0.552992 0.325073 0.434861 11.00000 -1.20000 AFIX 0 C2 1 0.515501 0.386634 0.681622 11.00000 0.03086 0.03312 = 0.02208 -0.00414 0.00425 -0.00469 AFIX 23 H2A 2 0.582997 0.342818 0.726073 11.00000 -1.20000 H2B 2 0.343461 0.409226 0.698365 11.00000 -1.20000 AFIX 0 C11 1 0.284339 0.289962 0.574577 11.00000 0.02418 0.02539 = 0.02501 -0.00031 0.00272 -0.00040 C12 1 0.260445 0.253207 0.487582 11.00000 0.02683 0.02755 = 0.02423 -0.00137 0.00566 -0.00108 C13 1 0.081484 0.187638 0.466195 11.00000 0.03016 0.02943 = 0.02548 -0.00405 0.00382 0.00004 AFIX 43 H13 2 0.064100 0.162560 0.407319 11.00000 -1.20000 AFIX 0 C14 1 -0.070342 0.159058 0.530160 11.00000 0.02482 0.02466 = 0.03229 0.00091 0.00170 -0.00235 C15 1 -0.049614 0.195294 0.616088 11.00000 0.02757 0.03127 = 0.02800 0.00358 0.00733 -0.00058 AFIX 43 H15 2 -0.156785 0.175297 0.659586 11.00000 -1.20000 AFIX 0 C16 1 0.127456 0.260635 0.638372 11.00000 0.02991 0.03168 = 0.02194 -0.00117 0.00543 -0.00055 AFIX 43 H16 2 0.142093 0.285547 0.697272 11.00000 -1.20000 AFIX 0 C21 1 0.727928 0.453218 0.685142 11.00000 0.02655 0.02770 = 0.02556 -0.00329 0.00391 0.00018 C22 1 0.788345 0.491518 0.607001 11.00000 0.03609 0.03560 = 0.02389 0.00021 0.00017 -0.00325 AFIX 43 H22 2 0.698484 0.474416 0.548135 11.00000 -1.20000 AFIX 0 C23 1 0.979078 0.554698 0.613874 11.00000 0.04430 0.03532 = 0.03284 0.00583 0.00771 -0.00539 AFIX 43 H23 2 1.018768 0.580552 0.559676 11.00000 -1.20000 AFIX 0 C24 1 1.111497 0.580282 0.698675 11.00000 0.04063 0.03317 = 0.03988 -0.00653 0.00971 -0.01047 AFIX 43 H24 2 1.242228 0.623541 0.703233 11.00000 -1.20000 AFIX 0 C25 1 1.052115 0.542441 0.776603 11.00000 0.04986 0.05258 = 0.02901 -0.01224 0.00599 -0.02116 AFIX 43 H25 2 1.141575 0.559899 0.835381 11.00000 -1.20000 AFIX 0 C26 1 0.862559 0.478970 0.770010 11.00000 0.04666 0.04923 = 0.02429 -0.00412 0.00712 -0.01804 AFIX 43 H26 2 0.824769 0.452907 0.824332 11.00000 -1.20000 AFIX 0 HKLF 4 REM ia354_a.res in P2(1)/n REM wR2 = 0.0880, GooF = S = 1.046, Restrained GooF = 1.046 for all data REM R1 = 0.0337 for 2378 Fo > 4sig(Fo) and 0.0457 for all 2917 data REM 154 parameters refined using 0 restraints END WGHT 0.0398 0.3701 REM Instructions for potential hydrogen bonds EQIV $1 x-1/2, -y+1/2, z+1/2 HTAB C16 O1_$1 REM Highest difference peak 0.324, deepest hole -0.186, 1-sigma level 0.040 Q1 1 0.3605 0.2606 0.4597 11.00000 0.05 0.32 Q2 1 0.1804 0.2826 0.6010 11.00000 0.05 0.28 Q3 1 0.6443 0.4220 0.6816 11.00000 0.05 0.26 Q4 1 0.2333 0.2779 0.5257 11.00000 0.05 0.25 Q5 1 0.7249 0.4828 0.6509 11.00000 0.05 0.25 Q6 1 -0.0352 0.1839 0.4884 11.00000 0.05 0.23 Q7 1 0.7520 0.4787 0.7221 11.00000 0.05 0.23 Q8 1 0.2640 0.2650 0.6135 11.00000 0.05 0.20 Q9 1 0.1777 0.2229 0.4794 11.00000 0.05 0.20 Q10 1 0.9237 0.5210 0.7720 11.00000 0.05 0.20 Q11 1 -0.0092 0.1697 0.5801 11.00000 0.05 0.19 Q12 1 0.9999 0.5760 0.6585 11.00000 0.05 0.19 Q13 1 1.0684 0.5539 0.6587 11.00000 0.05 0.19 Q14 1 0.8362 0.5375 0.6164 11.00000 0.05 0.19 Q15 1 -0.0020 0.2413 0.6157 11.00000 0.05 0.18 Q16 1 0.3548 0.3141 0.5832 11.00000 0.05 0.16 Q17 1 -0.2974 0.0764 0.4425 11.00000 0.05 0.15 Q18 1 0.0829 0.2168 0.6343 11.00000 0.05 0.14 Q19 1 0.0732 0.1753 0.4447 11.00000 0.05 0.13 Q20 1 1.0548 0.5636 0.7326 11.00000 0.05 0.13 ; _shelx_res_checksum 29235 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 -0.28696(8) 0.07555(2) 0.50325(3) 0.04078(12) Uani 1 1 d . . . . . O1 O 0.4157(2) 0.25123(7) 0.34328(7) 0.0459(3) Uani 1 1 d . . . . . O2 O 0.4633(2) 0.35370(6) 0.59046(6) 0.0318(2) Uani 1 1 d . . . . . C1 C 0.4281(3) 0.28108(9) 0.41874(10) 0.0344(3) Uani 1 1 d . . . . . H1 H 0.552992 0.325073 0.434861 0.041 Uiso 1 1 calc R U . . . C2 C 0.5155(3) 0.38663(8) 0.68162(9) 0.0287(3) Uani 1 1 d . . . . . H2A H 0.582997 0.342818 0.726073 0.034 Uiso 1 1 calc R U . . . H2B H 0.343461 0.409226 0.698365 0.034 Uiso 1 1 calc R U . . . C11 C 0.2843(3) 0.28996(7) 0.57458(9) 0.0250(3) Uani 1 1 d . . . . . C12 C 0.2604(3) 0.25321(8) 0.48758(9) 0.0260(3) Uani 1 1 d . . . . . C13 C 0.0815(3) 0.18764(8) 0.46620(9) 0.0284(3) Uani 1 1 d . . . . . H13 H 0.064100 0.162560 0.407319 0.034 Uiso 1 1 calc R U . . . C14 C -0.0703(3) 0.15906(8) 0.53016(9) 0.0276(3) Uani 1 1 d . . . . . C15 C -0.0496(3) 0.19529(8) 0.61609(9) 0.0286(3) Uani 1 1 d . . . . . H15 H -0.156785 0.175297 0.659586 0.034 Uiso 1 1 calc R U . . . C16 C 0.1275(3) 0.26064(8) 0.63837(9) 0.0277(3) Uani 1 1 d . . . . . H16 H 0.142093 0.285547 0.697272 0.033 Uiso 1 1 calc R U . . . C21 C 0.7279(3) 0.45322(8) 0.68514(9) 0.0266(3) Uani 1 1 d . . . . . C22 C 0.7883(3) 0.49152(9) 0.60700(9) 0.0324(3) Uani 1 1 d . . . . . H22 H 0.698484 0.474416 0.548135 0.039 Uiso 1 1 calc R U . . . C23 C 0.9791(3) 0.55470(9) 0.61387(10) 0.0373(3) Uani 1 1 d . . . . . H23 H 1.018768 0.580552 0.559676 0.045 Uiso 1 1 calc R U . . . C24 C 1.1115(3) 0.58028(9) 0.69867(10) 0.0375(3) Uani 1 1 d . . . . . H24 H 1.242228 0.623541 0.703233 0.045 Uiso 1 1 calc R U . . . C25 C 1.0521(3) 0.54244(10) 0.77660(10) 0.0438(4) Uani 1 1 d . . . . . H25 H 1.141575 0.559899 0.835381 0.053 Uiso 1 1 calc R U . . . C26 C 0.8626(3) 0.47897(10) 0.77001(10) 0.0399(4) Uani 1 1 d . . . . . H26 H 0.824769 0.452907 0.824332 0.048 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 0.0422(2) 0.03467(19) 0.0452(2) -0.00334(15) 0.00595(16) -0.01471(15) O1 0.0569(7) 0.0555(7) 0.0289(5) -0.0104(5) 0.0181(5) -0.0130(6) O2 0.0376(5) 0.0352(5) 0.0234(5) -0.0064(4) 0.0072(4) -0.0130(4) C1 0.0367(7) 0.0380(7) 0.0307(7) -0.0049(6) 0.0122(6) -0.0074(6) C2 0.0309(7) 0.0331(7) 0.0221(6) -0.0041(5) 0.0043(5) -0.0047(5) C11 0.0242(6) 0.0254(6) 0.0250(6) -0.0003(5) 0.0027(5) -0.0004(5) C12 0.0268(6) 0.0276(6) 0.0242(6) -0.0014(5) 0.0057(5) -0.0011(5) C13 0.0302(7) 0.0294(6) 0.0255(6) -0.0041(5) 0.0038(5) 0.0000(5) C14 0.0248(6) 0.0247(6) 0.0323(7) 0.0009(5) 0.0017(5) -0.0024(5) C15 0.0276(6) 0.0313(7) 0.0280(6) 0.0036(5) 0.0073(5) -0.0006(5) C16 0.0299(6) 0.0317(7) 0.0219(6) -0.0012(5) 0.0054(5) -0.0005(5) C21 0.0265(6) 0.0277(6) 0.0256(6) -0.0033(5) 0.0039(5) 0.0002(5) C22 0.0361(7) 0.0356(7) 0.0239(6) 0.0002(5) 0.0002(5) -0.0033(6) C23 0.0443(8) 0.0353(7) 0.0328(7) 0.0058(6) 0.0077(6) -0.0054(6) C24 0.0406(8) 0.0332(7) 0.0399(8) -0.0065(6) 0.0097(6) -0.0105(6) C25 0.0499(9) 0.0526(9) 0.0290(7) -0.0122(7) 0.0060(6) -0.0212(8) C26 0.0467(9) 0.0492(9) 0.0243(7) -0.0041(6) 0.0071(6) -0.0180(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 C11 O2 C2 117.61(10) . . ? O1 C1 C12 123.80(13) . . ? O1 C1 H1 118.1 . . ? C12 C1 H1 118.1 . . ? O2 C2 C21 108.89(10) . . ? O2 C2 H2A 109.9 . . ? C21 C2 H2A 109.9 . . ? O2 C2 H2B 109.9 . . ? C21 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O2 C11 C16 124.11(11) . . ? O2 C11 C12 116.24(11) . . ? C16 C11 C12 119.65(11) . . ? C13 C12 C11 119.60(11) . . ? C13 C12 C1 118.99(11) . . ? C11 C12 C1 121.38(12) . . ? C14 C13 C12 120.02(12) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.83(12) . . ? C13 C14 Cl1 119.41(10) . . ? C15 C14 Cl1 119.75(10) . . ? C16 C15 C14 119.83(12) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 120.07(12) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C22 C21 C26 118.62(12) . . ? C22 C21 C2 122.59(11) . . ? C26 C21 C2 118.76(12) . . ? C21 C22 C23 120.52(13) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 120.53(13) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C25 C24 C23 119.19(13) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.46(14) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 120.67(13) . . ? C21 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? 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 C14 1.7360(13) . ? O1 C1 1.2056(17) . ? O2 C11 1.3584(15) . ? O2 C2 1.4305(15) . ? C1 C12 1.4770(18) . ? C1 H1 0.9500 . ? C2 C21 1.5026(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C11 C16 1.3923(17) . ? C11 C12 1.4021(17) . ? C12 C13 1.3893(18) . ? C13 C14 1.3737(18) . ? C13 H13 0.9500 . ? C14 C15 1.3854(19) . ? C15 C16 1.3826(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.3826(18) . ? C21 C26 1.3832(19) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.378(2) . ? C23 H23 0.9500 . ? C24 C25 1.375(2) . ? C24 H24 0.9500 . ? C25 C26 1.387(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C1 H1 O2 0.95 2.45 2.7724(16) 100 . yes C22 H22 O2 0.95 2.42 2.7472(17) 100 . 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 C11 O2 C2 C21 177.23(11) . . . . ? C2 O2 C11 C16 7.15(18) . . . . ? C2 O2 C11 C12 -173.20(11) . . . . ? O2 C11 C12 C13 180.00(11) . . . . ? C16 C11 C12 C13 -0.34(19) . . . . ? O2 C11 C12 C1 1.88(18) . . . . ? C16 C11 C12 C1 -178.46(12) . . . . ? O1 C1 C12 C13 1.6(2) . . . . ? O1 C1 C12 C11 179.70(14) . . . . ? C11 C12 C13 C14 -0.14(19) . . . . ? C1 C12 C13 C14 178.03(12) . . . . ? C12 C13 C14 C15 0.6(2) . . . . ? C12 C13 C14 Cl1 -178.50(10) . . . . ? C13 C14 C15 C16 -0.5(2) . . . . ? Cl1 C14 C15 C16 178.55(10) . . . . ? C14 C15 C16 C11 0.0(2) . . . . ? O2 C11 C16 C15 -179.99(12) . . . . ? C12 C11 C16 C15 0.38(19) . . . . ? O2 C2 C21 C22 18.67(18) . . . . ? O2 C2 C21 C26 -163.33(12) . . . . ? C26 C21 C22 C23 -0.3(2) . . . . ? C2 C21 C22 C23 177.69(13) . . . . ? C21 C22 C23 C24 0.0(2) . . . . ? C22 C23 C24 C25 -0.1(2) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C22 C21 C26 C25 0.6(2) . . . . ? C2 C21 C26 C25 -177.44(15) . . . . ? C24 C25 C26 C21 -0.7(3) . . . . ?