#------------------------------------------------------------------------------ #$Date: 2020-04-30 04:29:10 +0300 (Thu, 30 Apr 2020) $ #$Revision: 251301 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240425.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_7240425 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_paper_doi 10.1039/C9RA10752E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C14 H11 Br O2' _chemical_formula_sum 'C14 H11 Br O2' _chemical_formula_weight 291.14 _chemical_melting_point 343 _chemical_name_common 2-(benzyloxy)-5-bromobenzaldehyde _chemical_name_systematic 5-bromo-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 _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _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 100.36(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.316(4) _cell_length_b 13.239(10) _cell_length_c 12.300(8) _cell_measurement_reflns_used 8261 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.82 _cell_measurement_theta_min 2.28 _cell_volume 1171.9(13) _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 0.997 _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 0.0268 _diffrn_reflns_av_unetI/netI 0.0213 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2920 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.374 _diffrn_reflns_theta_min 2.280 _exptl_absorpt_coefficient_mu 3.493 _exptl_absorpt_correction_T_max 0.745687 _exptl_absorpt_correction_T_min 0.614846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS V2008/4 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 584 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane/MeOH' _exptl_crystal_size_max 0.307 _exptl_crystal_size_mid 0.208 _exptl_crystal_size_min 0.199 _refine_diff_density_max 0.309 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2920 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0263 _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^)+(0.0285P)^2^+0.2957P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.0618 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2393 _reflns_number_total 2920 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10752e2.cif _cod_data_source_block ja017_tw _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240425 _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 0.414 _shelx_estimated_absorpt_t_max 0.543 _shelx_res_file ; TITL ja017_tw_a.res in P2(1)/n ja017_tw.res created by SHELXL-2018/3 at 13:38:24 on 10-Feb-2020 REM Old TITL ja017_tw in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.171, Rweak 0.012, Alpha 0.041 REM 0.971 for 116 systematic absences, Orientation as input REM Formula found by SHELXT: C14 O2 Br CELL 0.71073 7.3158 13.2390 12.3000 90.000 100.360 90.000 ZERR 4.000 0.0036 0.0102 0.0082 0.000 0.032 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H O BR UNIT 56 44 8 4 EQIV $1 3/2-x,-1/2+y,1/2-z HTAB C1 O2 HTAB C15 O1_$1 HTAB C22 O2 ACTA BOND $H CONF FMAP 2 HTAB L.S. 100 LIST 4 MERG 0 PLAN 20 SIZE 0.199 0.208 0.307 TEMP -73.150 REM WGHT 0.028500 0.295700 REM WGHT 0.028500 0.295700 REM WGHT 0.028500 0.295700 WGHT 0.028500 0.295700 BASF 0.44094 FVAR 0.38383 BR1 4 1.010399 0.475157 0.155935 11.00000 0.03937 0.04386 = 0.05790 -0.00238 0.02859 -0.00352 O1 3 0.442378 0.645461 0.325096 11.00000 0.04712 0.02337 = 0.05780 0.00372 0.02260 0.00486 O2 3 0.390233 0.356362 0.391371 11.00000 0.03894 0.02116 = 0.04746 0.00442 0.02347 0.00158 C1 1 0.436560 0.557625 0.349297 11.00000 0.03416 0.02770 = 0.03951 0.00124 0.01475 0.00300 AFIX 43 H1 2 0.346896 0.537339 0.392018 11.00000 -1.20000 AFIX 0 C2 1 0.349614 0.252838 0.408111 11.00000 0.03301 0.02210 = 0.04014 0.00052 0.01255 -0.00060 AFIX 23 H2A 2 0.456160 0.220489 0.456653 11.00000 -1.20000 H2B 2 0.327177 0.216738 0.336457 11.00000 -1.20000 AFIX 0 C11 1 0.535106 0.377790 0.339731 11.00000 0.02920 0.02530 = 0.02443 0.00052 0.00711 0.00102 C12 1 0.559622 0.479674 0.316866 11.00000 0.02921 0.02302 = 0.02637 -0.00056 0.00751 0.00223 C13 1 0.702831 0.508591 0.262400 11.00000 0.03039 0.02246 = 0.03010 0.00013 0.00810 -0.00125 AFIX 43 H13 2 0.719983 0.577700 0.246028 11.00000 -1.20000 AFIX 0 C14 1 0.818660 0.436148 0.232723 11.00000 0.02590 0.03230 = 0.02778 -0.00132 0.00812 -0.00080 C15 1 0.796655 0.334986 0.255800 11.00000 0.02754 0.02837 = 0.03088 -0.00385 0.00703 0.00522 AFIX 43 H15 2 0.878795 0.285940 0.235110 11.00000 -1.20000 AFIX 0 C16 1 0.654754 0.305991 0.308991 11.00000 0.03349 0.02091 = 0.03164 0.00046 0.00598 0.00348 AFIX 43 H16 2 0.638605 0.236645 0.324726 11.00000 -1.20000 AFIX 0 C21 1 0.180083 0.247119 0.460563 11.00000 0.02787 0.02678 = 0.02788 0.00391 0.00502 -0.00006 C22 1 0.116070 0.328425 0.514144 11.00000 0.03112 0.02994 = 0.03495 -0.00313 0.00556 -0.00205 AFIX 43 H22 2 0.176983 0.391923 0.515746 11.00000 -1.20000 AFIX 0 C23 1 -0.036838 0.317131 0.565411 11.00000 0.03427 0.04066 = 0.03633 -0.00504 0.00845 0.00437 AFIX 43 H23 2 -0.080127 0.373247 0.601717 11.00000 -1.20000 AFIX 0 C24 1 -0.126331 0.225967 0.564351 11.00000 0.02756 0.04868 = 0.03571 0.00521 0.00745 -0.00089 AFIX 43 H24 2 -0.229731 0.218714 0.600667 11.00000 -1.20000 AFIX 0 C25 1 -0.065096 0.144854 0.510152 11.00000 0.03592 0.03521 = 0.04124 0.00760 0.00719 -0.00632 AFIX 43 H25 2 -0.127282 0.081723 0.508423 11.00000 -1.20000 AFIX 0 C26 1 0.086953 0.155425 0.458280 11.00000 0.03521 0.02652 = 0.03749 0.00189 0.00893 -0.00089 AFIX 43 H26 2 0.127983 0.099424 0.420764 11.00000 -1.20000 AFIX 0 HKLF 5 REM ja017_tw_a.res in P2(1)/n REM wR2 = 0.0618, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0263 for 2393 Fo > 4sig(Fo) and 0.0387 for all 2920 data REM 155 parameters refined using 0 restraints END WGHT 0.0285 0.2957 REM Instructions for potential hydrogen bonds HTAB C15 O1_$1 REM Highest difference peak 0.309, deepest hole -0.334, 1-sigma level 0.063 Q1 1 0.2710 0.2514 0.4414 11.00000 0.05 0.31 Q2 1 1.0626 0.4237 0.1971 11.00000 0.05 0.27 Q3 1 0.7407 0.4634 0.2583 11.00000 0.05 0.26 Q4 1 0.6932 0.3223 0.2584 11.00000 0.05 0.25 Q5 1 0.8361 0.3998 0.2777 11.00000 0.05 0.24 Q6 1 0.7534 0.3806 0.2082 11.00000 0.05 0.23 Q7 1 0.1561 0.2024 0.4818 11.00000 0.05 0.23 Q8 1 0.2649 0.0764 0.5434 11.00000 0.05 0.22 Q9 1 0.6240 0.3429 0.3350 11.00000 0.05 0.22 Q10 1 0.3777 0.3012 0.4023 11.00000 0.05 0.21 Q11 1 0.3569 0.3109 0.3784 11.00000 0.05 0.21 Q12 1 0.6260 0.4874 0.2815 11.00000 0.05 0.21 Q13 1 0.6907 0.4612 0.0870 11.00000 0.05 0.20 Q14 1 1.0838 0.4786 0.2335 11.00000 0.05 0.20 Q15 1 0.1702 0.2797 0.5118 11.00000 0.05 0.19 Q16 1 -0.1427 0.1919 0.4893 11.00000 0.05 0.19 Q17 1 0.1110 0.2987 0.4563 11.00000 0.05 0.19 Q18 1 0.3006 0.4646 0.5930 11.00000 0.05 0.19 Q19 1 0.6361 0.2787 0.3036 11.00000 0.05 0.19 Q20 1 0.1876 0.5207 0.2753 11.00000 0.05 0.19 ; _shelx_res_checksum 83406 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 Br1 Br 1.01040(3) 0.47516(2) 0.15594(2) 0.04458(8) Uani 1 1 d . . . . . O1 O 0.4424(2) 0.64546(11) 0.32510(13) 0.0411(4) Uani 1 1 d . . . . . O2 O 0.39023(19) 0.35636(9) 0.39137(13) 0.0339(3) Uani 1 1 d . . . . . C1 C 0.4366(3) 0.55762(15) 0.34930(18) 0.0328(4) Uani 1 1 d . . . . . H1 H 0.346896 0.537339 0.392018 0.039 Uiso 1 1 calc R U . . . C2 C 0.3496(3) 0.25284(15) 0.40811(18) 0.0310(4) Uani 1 1 d . . . . . H2A H 0.456160 0.220489 0.456653 0.037 Uiso 1 1 calc R U . . . H2B H 0.327177 0.216738 0.336457 0.037 Uiso 1 1 calc R U . . . C11 C 0.5351(2) 0.37779(14) 0.33973(16) 0.0260(4) Uani 1 1 d . . . . . C12 C 0.5596(2) 0.47967(14) 0.31687(16) 0.0259(4) Uani 1 1 d . . . . . C13 C 0.7028(3) 0.50859(14) 0.26240(16) 0.0273(4) Uani 1 1 d . . . . . H13 H 0.719983 0.577700 0.246028 0.033 Uiso 1 1 calc R U . . . C14 C 0.8187(2) 0.43615(15) 0.23272(16) 0.0283(4) Uani 1 1 d . . . . . C15 C 0.7967(2) 0.33499(15) 0.25580(17) 0.0287(4) Uani 1 1 d . . . . . H15 H 0.878795 0.285940 0.235110 0.034 Uiso 1 1 calc R U . . . C16 C 0.6548(3) 0.30599(14) 0.30899(17) 0.0287(4) Uani 1 1 d . . . . . H16 H 0.638605 0.236645 0.324726 0.034 Uiso 1 1 calc R U . . . C21 C 0.1801(2) 0.24712(15) 0.46056(15) 0.0275(4) Uani 1 1 d . . . . . C22 C 0.1161(3) 0.32843(15) 0.51414(17) 0.0321(4) Uani 1 1 d . . . . . H22 H 0.176983 0.391923 0.515746 0.038 Uiso 1 1 calc R U . . . C23 C -0.0368(3) 0.31713(17) 0.56541(18) 0.0368(5) Uani 1 1 d . . . . . H23 H -0.080127 0.373247 0.601717 0.044 Uiso 1 1 calc R U . . . C24 C -0.1263(3) 0.22597(17) 0.56435(18) 0.0371(5) Uani 1 1 d . . . . . H24 H -0.229731 0.218714 0.600667 0.045 Uiso 1 1 calc R U . . . C25 C -0.0651(3) 0.14485(16) 0.51015(19) 0.0374(5) Uani 1 1 d . . . . . H25 H -0.127282 0.081723 0.508423 0.045 Uiso 1 1 calc R U . . . C26 C 0.0870(3) 0.15542(15) 0.45828(18) 0.0328(4) Uani 1 1 d . . . . . H26 H 0.127983 0.099424 0.420764 0.039 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 Br1 0.03937(13) 0.04386(13) 0.05790(15) -0.00238(11) 0.02859(10) -0.00352(9) O1 0.0471(8) 0.0234(7) 0.0578(10) 0.0037(7) 0.0226(8) 0.0049(6) O2 0.0389(7) 0.0212(6) 0.0475(9) 0.0044(6) 0.0235(7) 0.0016(5) C1 0.0342(10) 0.0277(10) 0.0395(12) 0.0012(9) 0.0147(9) 0.0030(8) C2 0.0330(9) 0.0221(8) 0.0401(11) 0.0005(9) 0.0126(8) -0.0006(8) C11 0.0292(9) 0.0253(9) 0.0244(9) 0.0005(8) 0.0071(7) 0.0010(7) C12 0.0292(9) 0.0230(9) 0.0264(9) -0.0006(8) 0.0075(7) 0.0022(7) C13 0.0304(9) 0.0225(9) 0.0301(10) 0.0001(8) 0.0081(8) -0.0012(7) C14 0.0259(9) 0.0323(10) 0.0278(10) -0.0013(8) 0.0081(8) -0.0008(7) C15 0.0275(9) 0.0284(9) 0.0309(10) -0.0039(8) 0.0070(8) 0.0052(7) C16 0.0335(10) 0.0209(9) 0.0316(11) 0.0005(8) 0.0060(8) 0.0035(7) C21 0.0279(9) 0.0268(9) 0.0279(10) 0.0039(8) 0.0050(7) -0.0001(8) C22 0.0311(9) 0.0299(10) 0.0350(11) -0.0031(9) 0.0056(8) -0.0021(8) C23 0.0343(11) 0.0407(12) 0.0363(12) -0.0050(10) 0.0084(9) 0.0044(9) C24 0.0276(9) 0.0487(13) 0.0357(12) 0.0052(10) 0.0074(8) -0.0009(8) C25 0.0359(10) 0.0352(11) 0.0412(13) 0.0076(10) 0.0072(9) -0.0063(8) C26 0.0352(10) 0.0265(10) 0.0375(11) 0.0019(9) 0.0089(8) -0.0009(8) 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' Br Br -0.2901 2.4595 '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 117.93(13) . . ? O1 C1 C12 124.09(18) . . ? O1 C1 H1 118.0 . . ? C12 C1 H1 118.0 . . ? O2 C2 C21 108.71(15) . . ? 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 124.49(17) . . ? O2 C11 C12 115.77(15) . . ? C16 C11 C12 119.74(17) . . ? C13 C12 C11 119.79(16) . . ? C13 C12 C1 119.14(17) . . ? C11 C12 C1 121.08(17) . . ? C14 C13 C12 119.28(17) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C15 121.44(17) . . ? C13 C14 Br1 119.29(15) . . ? C15 C14 Br1 119.26(13) . . ? C16 C15 C14 119.49(16) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C11 120.26(18) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C22 C21 C26 118.77(17) . . ? C22 C21 C2 122.78(18) . . ? C26 C21 C2 118.41(18) . . ? C21 C22 C23 120.07(19) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 120.85(19) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.55(18) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.07(19) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.68(19) . . ? C25 C26 H26 119.7 . . ? C21 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 Br1 C14 1.8981(19) . ? O1 C1 1.203(3) . ? O2 C11 1.360(2) . ? O2 C2 1.425(2) . ? C1 C12 1.471(3) . ? C1 H1 0.9500 . ? C2 C21 1.499(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C11 C16 1.390(3) . ? C11 C12 1.396(3) . ? C12 C13 1.395(2) . ? C13 C14 1.372(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C15 C16 1.377(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.387(3) . ? C21 C26 1.390(3) . ? C22 C23 1.387(3) . ? C22 H22 0.9500 . ? C23 C24 1.372(3) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C24 H24 0.9500 . ? C25 C26 1.385(3) . ? 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 2.42 2.747(3) 100 . yes C15 H15 O1 0.95 2.46 3.408(3) 173 2_645 yes C22 H22 O2 0.95 2.42 2.744(3) 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 -177.06(16) . . . . ? C2 O2 C11 C16 -4.8(3) . . . . ? C2 O2 C11 C12 174.77(17) . . . . ? O2 C11 C12 C13 -178.93(18) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? O2 C11 C12 C1 1.1(3) . . . . ? C16 C11 C12 C1 -179.38(19) . . . . ? O1 C1 C12 C13 5.5(3) . . . . ? O1 C1 C12 C11 -174.5(2) . . . . ? C11 C12 C13 C14 -0.5(3) . . . . ? C1 C12 C13 C14 179.55(19) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C12 C13 C14 Br1 178.73(15) . . . . ? C13 C14 C15 C16 0.5(3) . . . . ? Br1 C14 C15 C16 -178.34(15) . . . . ? C14 C15 C16 C11 -0.3(3) . . . . ? O2 C11 C16 C15 179.27(19) . . . . ? C12 C11 C16 C15 -0.2(3) . . . . ? O2 C2 C21 C22 -18.7(3) . . . . ? O2 C2 C21 C26 163.46(18) . . . . ? C26 C21 C22 C23 0.8(3) . . . . ? C2 C21 C22 C23 -177.08(19) . . . . ? C21 C22 C23 C24 0.2(3) . . . . ? C22 C23 C24 C25 -1.0(3) . . . . ? C23 C24 C25 C26 0.7(3) . . . . ? C24 C25 C26 C21 0.4(3) . . . . ? C22 C21 C26 C25 -1.1(3) . . . . ? C2 C21 C26 C25 176.9(2) . . . . ?