#------------------------------------------------------------------------------ #$Date: 2020-04-30 04:29:10 +0300 (Thu, 30 Apr 2020) $ #$Revision: 251301 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240429.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_7240429 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_absolute_configuration unk _chemical_formula_moiety 'C14 H10 Br2 O2' _chemical_formula_sum 'C14 H10 Br2 O2' _chemical_formula_weight 370.04 _chemical_melting_point 340 _chemical_name_common 2-(benzyloxy)-3,5-dibromobenzaldehyde _chemical_name_systematic 3,5-dibromo-2-(phenylmethoxy)benzaldehyde _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.0992(2) _cell_length_b 17.1619(7) _cell_length_c 18.9382(8) _cell_measurement_reflns_used 9926 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 27.12 _cell_measurement_theta_min 2.46 _cell_volume 1332.30(10) _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 1.000 _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 0.0332 _diffrn_reflns_av_unetI/netI 0.0241 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 34685 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.325 _diffrn_reflns_theta_min 1.601 _exptl_absorpt_coefficient_mu 6.074 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7522 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rod _exptl_crystal_F_000 720 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane/water' _exptl_crystal_size_max 0.597 _exptl_crystal_size_mid 0.043 _exptl_crystal_size_min 0.038 _refine_diff_density_max 0.311 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.015(11) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 3341 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0218 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0229P)^2^+0.2003P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0472 _reflns_Friedel_coverage 0.678 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 3010 _reflns_number_total 3341 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10752e2.cif _cod_data_source_block ja027 _cod_database_code 7240429 _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 0.122 _shelx_estimated_absorpt_t_max 0.802 _shelx_res_file ; TITL ja027_a.res in P2(1)2(1)2(1) ja027.res created by SHELXL-2018/3 at 14:10:25 on 10-Feb-2020 REM Old TITL ja027_s_P212121 in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.129, Rweak 0.020, Alpha 0.003 REM 0.820 for 26 systematic absences, Orientation as input REM Flack x = -0.076 ( 0.157 ) from 931 Parsons' quotients REM Formula found by SHELXT: C14 O2 Br2 CELL 0.71073 4.0992 17.1619 18.9382 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0007 0.0008 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H O BR UNIT 56 40 8 8 EQIV $1 -1/2+x,3/2-y,1-z EQIV $2 -1+x,y,z HTAB C1 O2 HTAB C2 O1_$1 HTAB C2 O2_$2 ACTA BOND $H CONF FMAP 2 HTAB L.S. 100 LIST 4 PLAN 20 SIZE 0.038 0.043 0.597 TEMP -73.130 TWIN MPLA C11 > C16 MPLA C21 > C26 REM WGHT 0.022900 0.200000 REM WGHT 0.022900 0.200300 REM WGHT 0.022900 0.200300 WGHT 0.022900 0.200300 BASF 0.01487 FVAR 0.16953 BR1 4 0.216215 0.491833 0.721248 11.00000 0.04667 0.02260 = 0.03675 0.00194 0.00300 -0.00502 BR2 4 0.094188 0.803728 0.808394 11.00000 0.05081 0.03294 = 0.04506 -0.01478 -0.00093 0.01043 O1 3 0.757195 0.795099 0.558164 11.00000 0.06186 0.04054 = 0.04830 0.01339 0.00564 -0.01068 O2 3 0.595172 0.568100 0.598458 11.00000 0.02034 0.03080 = 0.02737 -0.00612 -0.00341 0.00439 C1 1 0.710839 0.728059 0.570467 11.00000 0.02865 0.03316 = 0.02540 0.00763 -0.00456 -0.00221 AFIX 43 H1 2 0.797638 0.690204 0.539057 11.00000 -1.20000 AFIX 0 C2 1 0.365042 0.540989 0.544482 11.00000 0.02544 0.03304 = 0.02864 -0.00400 -0.00737 0.00613 AFIX 23 H2A 2 0.299296 0.584675 0.513451 11.00000 -1.20000 H2B 2 0.167106 0.519083 0.566911 11.00000 -1.20000 AFIX 0 C11 1 0.465303 0.621410 0.644545 11.00000 0.01897 0.02424 = 0.02442 -0.00212 -0.00515 0.00317 C12 1 0.295454 0.598389 0.703960 11.00000 0.02410 0.01958 = 0.02914 -0.00029 -0.00540 0.00070 C13 1 0.181345 0.652164 0.753087 11.00000 0.02663 0.02852 = 0.02509 -0.00134 -0.00047 0.00034 AFIX 43 H13 2 0.064672 0.635802 0.793815 11.00000 -1.20000 AFIX 0 C14 1 0.243621 0.730682 0.740645 11.00000 0.02996 0.02413 = 0.03090 -0.00711 -0.00467 0.00535 C15 1 0.408663 0.755172 0.682297 11.00000 0.03196 0.02069 = 0.03630 0.00204 -0.00812 0.00063 AFIX 43 H15 2 0.446795 0.809171 0.674971 11.00000 -1.20000 AFIX 0 C16 1 0.521445 0.700826 0.633374 11.00000 0.02266 0.02803 = 0.02887 0.00490 -0.00558 -0.00158 C21 1 0.538593 0.479536 0.502670 11.00000 0.02189 0.03035 = 0.02705 -0.00353 -0.00605 0.00051 C22 1 0.662420 0.495183 0.436670 11.00000 0.03770 0.03717 = 0.02902 0.00025 -0.00125 -0.00067 AFIX 43 H22 2 0.637466 0.545784 0.417062 11.00000 -1.20000 AFIX 0 C23 1 0.823416 0.437930 0.398362 11.00000 0.04051 0.06460 = 0.02781 -0.01250 0.00365 -0.00296 AFIX 43 H23 2 0.909534 0.449524 0.352991 11.00000 -1.20000 AFIX 0 C24 1 0.857940 0.364457 0.426211 11.00000 0.03857 0.04710 = 0.04639 -0.02294 0.00037 0.00695 AFIX 43 H24 2 0.965842 0.325004 0.399894 11.00000 -1.20000 AFIX 0 C25 1 0.735811 0.348069 0.492384 11.00000 0.04181 0.02940 = 0.05572 -0.00649 -0.00402 0.00397 AFIX 43 H25 2 0.760047 0.297314 0.511707 11.00000 -1.20000 AFIX 0 C26 1 0.578710 0.405169 0.530521 11.00000 0.03242 0.03394 = 0.03350 0.00140 0.00306 0.00077 AFIX 43 H26 2 0.496973 0.393648 0.576285 11.00000 -1.20000 AFIX 0 HKLF 4 REM ja027_a.res in P2(1)2(1)2(1) REM wR2 = 0.0472, GooF = S = 1.042, Restrained GooF = 1.042 for all data REM R1 = 0.0218 for 3010 Fo > 4sig(Fo) and 0.0276 for all 3341 data REM 164 parameters refined using 0 restraints END WGHT 0.0229 0.2003 REM Instructions for potential hydrogen bonds EQIV $3 x+1/2, -y+3/2, -z+1 HTAB C1 O1_$3 HTAB C2 O1_$1 HTAB C2 Br1 REM Highest difference peak 0.311, deepest hole -0.263, 1-sigma level 0.054 Q1 1 0.3401 0.8014 0.8109 11.00000 0.05 0.31 Q2 1 0.4436 0.4898 0.7249 11.00000 0.05 0.29 Q3 1 0.2181 0.4848 0.7721 11.00000 0.05 0.28 Q4 1 0.0660 0.8226 0.7709 11.00000 0.05 0.28 Q5 1 -0.1632 0.8043 0.8082 11.00000 0.05 0.27 Q6 1 0.6505 0.7008 0.5873 11.00000 0.05 0.27 Q7 1 -0.0623 0.4932 0.7209 11.00000 0.05 0.26 Q8 1 0.4926 0.6643 0.6431 11.00000 0.05 0.23 Q9 1 0.1664 0.6915 0.7382 11.00000 0.05 0.23 Q10 1 0.4977 0.7195 0.6723 11.00000 0.05 0.23 Q11 1 0.0526 0.7664 0.8052 11.00000 0.05 0.23 Q12 1 0.3067 0.6303 0.7279 11.00000 0.05 0.23 Q13 1 0.1981 0.6325 0.7211 11.00000 0.05 0.23 Q14 1 0.7883 0.4606 0.4315 11.00000 0.05 0.22 Q15 1 0.5305 0.5896 0.6234 11.00000 0.05 0.21 Q16 1 0.5600 0.4412 0.5128 11.00000 0.05 0.21 Q17 1 0.2955 0.4932 0.6737 11.00000 0.05 0.21 Q18 1 -0.0024 0.8077 0.8405 11.00000 0.05 0.21 Q19 1 0.1599 0.7556 0.8495 11.00000 0.05 0.21 Q20 1 0.2729 0.5414 0.7598 11.00000 0.05 0.20 ; _shelx_res_checksum 59208 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 Br1 Br 0.21621(8) 0.49183(2) 0.72125(2) 0.03534(9) Uani 1 1 d . . . . . Br2 Br 0.09419(9) 0.80373(2) 0.80839(2) 0.04293(10) Uani 1 1 d . . . . . O1 O 0.7572(7) 0.79510(13) 0.55816(13) 0.0502(6) Uani 1 1 d . . . . . O2 O 0.5952(5) 0.56810(11) 0.59846(10) 0.0262(4) Uani 1 1 d . . . . . C1 C 0.7108(8) 0.72806(17) 0.57047(15) 0.0291(6) Uani 1 1 d . . . . . H1 H 0.797638 0.690204 0.539057 0.035 Uiso 1 1 calc R U . . . C2 C 0.3650(8) 0.54099(17) 0.54448(16) 0.0290(7) Uani 1 1 d . . . . . H2A H 0.299296 0.584675 0.513451 0.035 Uiso 1 1 calc R U . . . H2B H 0.167106 0.519083 0.566911 0.035 Uiso 1 1 calc R U . . . C11 C 0.4653(6) 0.62141(16) 0.64455(15) 0.0225(6) Uani 1 1 d . . . . . C12 C 0.2955(7) 0.59839(14) 0.70396(14) 0.0243(6) Uani 1 1 d . . . . . C13 C 0.1813(7) 0.65216(15) 0.75309(15) 0.0267(6) Uani 1 1 d . . . . . H13 H 0.064672 0.635802 0.793815 0.032 Uiso 1 1 calc R U . . . C14 C 0.2436(8) 0.73068(15) 0.74064(15) 0.0283(6) Uani 1 1 d . . . . . C15 C 0.4087(8) 0.75517(16) 0.68230(16) 0.0297(6) Uani 1 1 d . . . . . H15 H 0.446795 0.809171 0.674971 0.036 Uiso 1 1 calc R U . . . C16 C 0.5214(7) 0.70083(17) 0.63337(16) 0.0265(6) Uani 1 1 d . . . . . C21 C 0.5386(7) 0.47954(17) 0.50267(15) 0.0264(6) Uani 1 1 d . . . . . C22 C 0.6624(7) 0.49518(19) 0.43667(16) 0.0346(7) Uani 1 1 d . . . . . H22 H 0.637466 0.545784 0.417062 0.042 Uiso 1 1 calc R U . . . C23 C 0.8234(9) 0.4379(2) 0.39836(18) 0.0443(9) Uani 1 1 d . . . . . H23 H 0.909534 0.449524 0.352991 0.053 Uiso 1 1 calc R U . . . C24 C 0.8579(9) 0.3645(2) 0.42621(19) 0.0440(9) Uani 1 1 d . . . . . H24 H 0.965842 0.325004 0.399894 0.053 Uiso 1 1 calc R U . . . C25 C 0.7358(9) 0.34807(18) 0.49238(19) 0.0423(8) Uani 1 1 d . . . . . H25 H 0.760047 0.297314 0.511707 0.051 Uiso 1 1 calc R U . . . C26 C 0.5787(8) 0.40517(17) 0.53052(17) 0.0333(7) Uani 1 1 d . . . . . H26 H 0.496973 0.393648 0.576285 0.040 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 0.04667(18) 0.02260(13) 0.03675(16) 0.00194(12) 0.00300(15) -0.00502(13) Br2 0.0508(2) 0.03294(16) 0.04506(19) -0.01478(15) -0.00093(17) 0.01043(15) O1 0.0619(17) 0.0405(13) 0.0483(14) 0.0134(11) 0.0056(14) -0.0107(14) O2 0.0203(9) 0.0308(10) 0.0274(10) -0.0061(8) -0.0034(9) 0.0044(9) C1 0.0287(15) 0.0332(15) 0.0254(14) 0.0076(11) -0.0046(13) -0.0022(13) C2 0.0254(16) 0.0330(15) 0.0286(15) -0.0040(12) -0.0074(13) 0.0061(12) C11 0.0190(13) 0.0242(13) 0.0244(14) -0.0021(11) -0.0052(11) 0.0032(10) C12 0.0241(13) 0.0196(12) 0.0291(15) -0.0003(10) -0.0054(11) 0.0007(11) C13 0.0266(15) 0.0285(13) 0.0251(13) -0.0013(12) -0.0005(12) 0.0003(12) C14 0.0300(15) 0.0241(12) 0.0309(15) -0.0071(11) -0.0047(13) 0.0053(12) C15 0.0320(15) 0.0207(13) 0.0363(17) 0.0020(12) -0.0081(15) 0.0006(12) C16 0.0227(14) 0.0280(14) 0.0289(15) 0.0049(12) -0.0056(11) -0.0016(12) C21 0.0219(14) 0.0304(15) 0.0270(15) -0.0035(12) -0.0060(12) 0.0005(12) C22 0.0377(17) 0.0372(16) 0.0290(16) 0.0003(13) -0.0013(13) -0.0007(15) C23 0.041(2) 0.065(2) 0.0278(17) -0.0125(16) 0.0036(15) -0.0030(18) C24 0.0386(19) 0.047(2) 0.046(2) -0.0229(16) 0.0004(16) 0.0069(16) C25 0.0418(19) 0.0294(15) 0.056(2) -0.0065(14) -0.0040(18) 0.0040(17) C26 0.0324(17) 0.0339(17) 0.0335(16) 0.0014(13) 0.0031(15) 0.0008(14) 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 113.9(2) . . ? O1 C1 C16 122.7(3) . . ? O1 C1 H1 118.6 . . ? C16 C1 H1 118.6 . . ? O2 C2 C21 106.6(2) . . ? O2 C2 H2A 110.4 . . ? C21 C2 H2A 110.4 . . ? O2 C2 H2B 110.4 . . ? C21 C2 H2B 110.4 . . ? H2A C2 H2B 108.6 . . ? O2 C11 C12 121.5(2) . . ? O2 C11 C16 119.3(3) . . ? C12 C11 C16 119.0(3) . . ? C11 C12 C13 121.6(2) . . ? C11 C12 Br1 120.4(2) . . ? C13 C12 Br1 118.0(2) . . ? C12 C13 C14 117.9(3) . . ? C12 C13 H13 121.1 . . ? C14 C13 H13 121.1 . . ? C15 C14 C13 121.8(3) . . ? C15 C14 Br2 120.4(2) . . ? C13 C14 Br2 117.8(2) . . ? C14 C15 C16 119.8(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C11 119.8(3) . . ? C15 C16 C1 119.5(3) . . ? C11 C16 C1 120.7(3) . . ? C22 C21 C26 118.7(3) . . ? C22 C21 C2 121.2(3) . . ? C26 C21 C2 120.1(3) . . ? C21 C22 C23 120.8(3) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 119.9(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 119.9(3) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C26 C25 C24 120.1(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C21 120.6(3) . . ? 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 C12 1.886(2) . ? Br2 C14 1.896(3) . ? O1 C1 1.189(3) . ? O2 C11 1.372(3) . ? O2 C2 1.467(3) . ? C1 C16 1.497(4) . ? C1 H1 0.9500 . ? C2 C21 1.498(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C11 C12 1.381(4) . ? C11 C16 1.398(4) . ? C12 C13 1.391(4) . ? C13 C14 1.392(4) . ? C13 H13 0.9500 . ? C14 C15 1.362(4) . ? C15 C16 1.394(4) . ? C15 H15 0.9500 . ? C21 C22 1.376(4) . ? C21 C26 1.391(4) . ? C22 C23 1.388(5) . ? C22 H22 0.9500 . ? C23 C24 1.374(5) . ? C23 H23 0.9500 . ? C24 C25 1.378(5) . ? C24 H24 0.9500 . ? C25 C26 1.377(4) . ? 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 2.52 2.836(3) 100 . yes C2 H2A O1 0.99 2.48 3.448(4) 167 4_466 yes C2 H2B O2 0.99 2.56 3.350(4) 137 1_455 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 -176.0(2) . . . . ? C2 O2 C11 C12 85.6(3) . . . . ? C2 O2 C11 C16 -98.0(3) . . . . ? O2 C11 C12 C13 175.9(3) . . . . ? C16 C11 C12 C13 -0.5(4) . . . . ? O2 C11 C12 Br1 -3.3(4) . . . . ? C16 C11 C12 Br1 -179.7(2) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? Br1 C12 C13 C14 179.2(2) . . . . ? C12 C13 C14 C15 0.4(5) . . . . ? C12 C13 C14 Br2 -179.0(2) . . . . ? C13 C14 C15 C16 -0.3(5) . . . . ? Br2 C14 C15 C16 179.1(2) . . . . ? C14 C15 C16 C11 -0.2(4) . . . . ? C14 C15 C16 C1 -178.3(3) . . . . ? O2 C11 C16 C15 -175.9(3) . . . . ? C12 C11 C16 C15 0.6(4) . . . . ? O2 C11 C16 C1 2.2(4) . . . . ? C12 C11 C16 C1 178.6(2) . . . . ? O1 C1 C16 C15 -3.8(5) . . . . ? O1 C1 C16 C11 178.1(3) . . . . ? O2 C2 C21 C22 -103.1(3) . . . . ? O2 C2 C21 C26 76.5(4) . . . . ? C26 C21 C22 C23 0.2(5) . . . . ? C2 C21 C22 C23 179.9(3) . . . . ? C21 C22 C23 C24 0.5(5) . . . . ? C22 C23 C24 C25 -0.7(6) . . . . ? C23 C24 C25 C26 0.1(6) . . . . ? C24 C25 C26 C21 0.6(5) . . . . ? C22 C21 C26 C25 -0.8(5) . . . . ? C2 C21 C26 C25 179.5(3) . . . . ?