#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:10:02 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257956 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240427.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_7240427 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 H12 O2' _chemical_formula_sum 'C14 H12 O2' _chemical_formula_weight 212.24 _chemical_melting_point 373 _chemical_name_common 4-(benzyloxy)benzaldehyde _chemical_name_systematic 4-(phenylmethoxybenzaldehyde _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.5088(5) _cell_length_b 12.9889(6) _cell_length_c 7.2608(4) _cell_measurement_reflns_used 9954 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 28.25 _cell_measurement_theta_min 2.36 _cell_volume 1085.39(9) _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0152 _diffrn_reflns_av_unetI/netI 0.0090 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 19779 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.319 _diffrn_reflns_theta_min 2.364 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_crystal_colour off-white _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 448 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane/water' _exptl_crystal_size_max 0.620 _exptl_crystal_size_mid 0.255 _exptl_crystal_size_min 0.190 _refine_diff_density_max 0.212 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.031 _refine_ls_abs_structure_details ; Flack x determined using 1155 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(15) _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 145 _refine_ls_number_reflns 2698 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0295 _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^)+(0.0474P)^2^+0.1324P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.0822 _reflns_Friedel_coverage 0.853 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 2581 _reflns_number_total 2698 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10752e2.cif _cod_data_source_block ia376 _cod_depositor_comments 'Adding full bibliography for 7240424--7240429.cif.' _cod_database_code 7240427 _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 0.949 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; TITL ia376_a.res in Pna2(1) ia376.res created by SHELXL-2018/3 at 15:43:39 on 18-Feb-2019 REM Old TITL ia376_s_Pna21 in Pna2(1) REM SHELXT solution in Pna2(1): R1 0.101, Rweak 0.007, Alpha 0.001 REM 0.941 for 118 systematic absences, Orientation as input REM Flack x = -9.990 ( 9.990 ) from 955 Parsons' quotients REM Formula found by SHELXT: C14 O2 CELL 0.71073 11.5088 12.9889 7.2608 90.000 90.000 90.000 ZERR 4.000 0.0005 0.0006 0.0004 0.000 0.000 0.000 LATT -1 SYMM -X, -Y, 1/2+Z SYMM 1/2+X, 1/2-Y, Z SYMM 1/2-X, 1/2+Y, 1/2+Z SFAC C H O UNIT 56 48 8 EQIV $1 -1/2+x,3/2-y,z EQIV $2 3/2-x,-1/2+y,1/2+z HTAB C2 O1_$1 HTAB C2 O1_$2 HTAB C22 O2 ACTA BOND $H CONF FMAP 2 HTAB L.S. 100 LIST 4 PLAN -20 SIZE 0.19 0.255 0.62 TEMP -73.130 REM WGHT 0.047300 0.132800 REM WGHT 0.047400 0.132400 REM WGHT 0.047300 0.132800 WGHT 0.047400 0.132400 FVAR 0.30694 O1 3 0.810844 0.921740 0.450832 11.00000 0.04669 0.03486 = 0.06823 0.00269 0.00402 -0.00805 O2 3 0.636646 0.455454 0.461879 11.00000 0.03686 0.02724 = 0.04109 -0.00431 0.01274 -0.00321 C1 1 0.733849 0.876092 0.528327 11.00000 0.03684 0.03056 = 0.04238 -0.00389 -0.00465 0.00021 AFIX 43 H1 2 0.683842 0.915339 0.605181 11.00000 -1.20000 AFIX 0 C2 1 0.539816 0.411177 0.556365 11.00000 0.02995 0.02939 = 0.03277 -0.00203 0.00450 -0.00097 AFIX 23 H2A 2 0.466725 0.442683 0.511732 11.00000 -1.20000 H2B 2 0.546465 0.424734 0.690125 11.00000 -1.20000 AFIX 0 C11 1 0.655855 0.557852 0.486051 11.00000 0.03066 0.02667 = 0.02789 -0.00132 0.00141 -0.00003 C12 1 0.581648 0.623228 0.582077 11.00000 0.02771 0.03257 = 0.03244 -0.00356 0.00502 -0.00157 AFIX 43 H12 2 0.512705 0.597536 0.637437 11.00000 -1.20000 AFIX 0 C13 1 0.610405 0.726678 0.595309 11.00000 0.03228 0.03202 = 0.03119 -0.00592 0.00292 0.00301 AFIX 43 H13 2 0.560573 0.771972 0.660995 11.00000 -1.20000 AFIX 0 C14 1 0.710484 0.765204 0.514490 11.00000 0.03033 0.02717 = 0.02784 -0.00067 -0.00372 0.00035 C15 1 0.784707 0.698660 0.419771 11.00000 0.02750 0.03337 = 0.03179 0.00239 0.00298 -0.00048 AFIX 43 H15 2 0.853959 0.724351 0.365386 11.00000 -1.20000 AFIX 0 C16 1 0.757510 0.596098 0.405325 11.00000 0.03089 0.03048 = 0.03346 -0.00129 0.00613 0.00406 AFIX 43 H16 2 0.807838 0.550923 0.340330 11.00000 -1.20000 AFIX 0 C21 1 0.537597 0.297064 0.522116 11.00000 0.02658 0.02826 = 0.02573 0.00096 -0.00227 0.00089 C22 1 0.628286 0.244264 0.438238 11.00000 0.02732 0.03204 = 0.03363 0.00154 0.00194 0.00086 AFIX 43 H22 2 0.695453 0.280671 0.398962 11.00000 -1.20000 AFIX 0 C23 1 0.621312 0.138647 0.411504 11.00000 0.03449 0.03396 = 0.04426 -0.00155 0.00095 0.00836 AFIX 43 H23 2 0.683447 0.103097 0.353410 11.00000 -1.20000 AFIX 0 C24 1 0.523724 0.084854 0.469486 11.00000 0.04496 0.02652 = 0.04927 0.00262 -0.00462 0.00059 AFIX 43 H24 2 0.518799 0.012617 0.450541 11.00000 -1.20000 AFIX 0 C25 1 0.433792 0.136678 0.554818 11.00000 0.03664 0.03617 = 0.04724 0.00535 0.00188 -0.00714 AFIX 43 H25 2 0.367306 0.099935 0.595960 11.00000 -1.20000 AFIX 0 C26 1 0.440506 0.242253 0.580444 11.00000 0.02959 0.03668 = 0.03682 0.00030 0.00553 -0.00107 AFIX 43 H26 2 0.378151 0.277546 0.638446 11.00000 -1.20000 AFIX 0 HKLF 4 REM ia376_a.res in Pna2(1) REM wR2 = 0.0822, GooF = S = 1.047, Restrained GooF = 1.047 for all data REM R1 = 0.0295 for 2581 Fo > 4sig(Fo) and 0.0315 for all 2698 data REM 145 parameters refined using 1 restraints END WGHT 0.0473 0.1328 REM Instructions for potential hydrogen bonds HTAB C2 O1_$1 HTAB C2 O1_$2 REM Highest difference peak 0.212, deepest hole -0.159, 1-sigma level 0.031 Q1 1 0.5428 0.3534 0.5299 11.00000 0.05 0.21 Q2 1 0.7200 0.8149 0.5131 11.00000 0.05 0.21 Q3 1 0.6260 0.1897 0.4352 11.00000 0.05 0.19 Q4 1 0.5972 0.6775 0.5718 11.00000 0.05 0.18 Q5 1 0.4413 0.1862 0.5671 11.00000 0.05 0.17 Q6 1 0.7721 0.6452 0.4440 11.00000 0.05 0.16 Q7 1 0.6330 0.5903 0.5664 11.00000 0.05 0.14 Q8 1 0.5949 0.2695 0.5183 11.00000 0.05 0.14 Q9 1 0.5764 0.2683 0.4681 11.00000 0.05 0.14 Q10 1 0.6960 0.5808 0.4260 11.00000 0.05 0.14 Q11 1 0.4864 0.1165 0.5228 11.00000 0.05 0.14 Q12 1 0.7163 0.5757 0.4741 11.00000 0.05 0.13 Q13 1 0.7395 0.7299 0.4664 11.00000 0.05 0.13 Q14 1 0.6557 0.5040 0.4974 11.00000 0.05 0.12 Q15 1 0.5665 0.1193 0.4347 11.00000 0.05 0.12 Q16 1 0.4938 0.2672 0.5449 11.00000 0.05 0.12 Q17 1 0.6566 0.7484 0.5494 11.00000 0.05 0.11 Q18 1 0.3474 0.1010 0.4960 11.00000 0.05 0.09 Q19 1 0.8017 0.8735 0.5140 11.00000 0.05 0.08 Q20 1 0.8678 0.8823 0.4264 11.00000 0.05 0.08 ; _shelx_res_checksum 4530 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, 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 O1 O 0.81084(10) 0.92174(9) 0.4508(2) 0.0499(3) Uani 1 1 d . . . . . O2 O 0.63665(9) 0.45545(8) 0.46188(17) 0.0351(3) Uani 1 1 d . . . . . C1 C 0.73385(14) 0.87609(12) 0.5283(2) 0.0366(3) Uani 1 1 d . . . . . H1 H 0.683842 0.915339 0.605181 0.044 Uiso 1 1 calc R U . . . C2 C 0.53982(12) 0.41118(11) 0.5564(2) 0.0307(3) Uani 1 1 d . . . . . H2A H 0.466725 0.442683 0.511732 0.037 Uiso 1 1 calc R U . . . H2B H 0.546465 0.424734 0.690125 0.037 Uiso 1 1 calc R U . . . C11 C 0.65585(12) 0.55785(10) 0.4861(2) 0.0284(3) Uani 1 1 d . . . . . C12 C 0.58165(12) 0.62323(11) 0.5821(2) 0.0309(3) Uani 1 1 d . . . . . H12 H 0.512705 0.597536 0.637437 0.037 Uiso 1 1 calc R U . . . C13 C 0.61041(13) 0.72668(12) 0.5953(2) 0.0318(3) Uani 1 1 d . . . . . H13 H 0.560573 0.771972 0.660995 0.038 Uiso 1 1 calc R U . . . C14 C 0.71048(12) 0.76520(10) 0.5145(2) 0.0284(3) Uani 1 1 d . . . . . C15 C 0.78471(12) 0.69866(11) 0.4198(2) 0.0309(3) Uani 1 1 d . . . . . H15 H 0.853959 0.724351 0.365386 0.037 Uiso 1 1 calc R U . . . C16 C 0.75751(13) 0.59610(11) 0.4053(2) 0.0316(3) Uani 1 1 d . . . . . H16 H 0.807838 0.550923 0.340330 0.038 Uiso 1 1 calc R U . . . C21 C 0.53760(12) 0.29706(10) 0.52212(19) 0.0269(3) Uani 1 1 d . . . . . C22 C 0.62829(12) 0.24426(11) 0.4382(2) 0.0310(3) Uani 1 1 d . . . . . H22 H 0.695453 0.280671 0.398962 0.037 Uiso 1 1 calc R U . . . C23 C 0.62131(14) 0.13865(12) 0.4115(2) 0.0376(4) Uani 1 1 d . . . . . H23 H 0.683447 0.103097 0.353410 0.045 Uiso 1 1 calc R U . . . C24 C 0.52372(15) 0.08485(12) 0.4695(3) 0.0402(4) Uani 1 1 d . . . . . H24 H 0.518799 0.012617 0.450541 0.048 Uiso 1 1 calc R U . . . C25 C 0.43379(15) 0.13668(12) 0.5548(3) 0.0400(4) Uani 1 1 d . . . . . H25 H 0.367306 0.099935 0.595960 0.048 Uiso 1 1 calc R U . . . C26 C 0.44051(13) 0.24225(12) 0.5804(2) 0.0344(3) Uani 1 1 d . . . . . H26 H 0.378151 0.277546 0.638446 0.041 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 O1 0.0467(7) 0.0349(6) 0.0682(9) 0.0027(6) 0.0040(7) -0.0081(5) O2 0.0369(5) 0.0272(5) 0.0411(6) -0.0043(5) 0.0127(5) -0.0032(4) C1 0.0368(8) 0.0306(7) 0.0424(9) -0.0039(7) -0.0046(7) 0.0002(6) C2 0.0300(7) 0.0294(7) 0.0328(8) -0.0020(6) 0.0045(6) -0.0010(5) C11 0.0307(6) 0.0267(6) 0.0279(7) -0.0013(5) 0.0014(5) 0.0000(5) C12 0.0277(6) 0.0326(7) 0.0324(7) -0.0036(6) 0.0050(6) -0.0016(5) C13 0.0323(7) 0.0320(7) 0.0312(7) -0.0059(6) 0.0029(6) 0.0030(6) C14 0.0303(7) 0.0272(6) 0.0278(6) -0.0007(6) -0.0037(5) 0.0004(5) C15 0.0275(6) 0.0334(7) 0.0318(7) 0.0024(6) 0.0030(6) -0.0005(5) C16 0.0309(7) 0.0305(7) 0.0335(7) -0.0013(6) 0.0061(6) 0.0041(5) C21 0.0266(6) 0.0283(6) 0.0257(7) 0.0010(5) -0.0023(5) 0.0009(5) C22 0.0273(6) 0.0320(7) 0.0336(8) 0.0015(6) 0.0019(5) 0.0009(5) C23 0.0345(7) 0.0340(8) 0.0443(10) -0.0016(7) 0.0010(7) 0.0084(6) C24 0.0450(9) 0.0265(6) 0.0493(10) 0.0026(7) -0.0046(8) 0.0006(6) C25 0.0366(8) 0.0362(8) 0.0472(10) 0.0054(7) 0.0019(7) -0.0071(6) C26 0.0296(6) 0.0367(7) 0.0368(8) 0.0003(7) 0.0055(6) -0.0011(6) 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' 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 117.28(11) . . ? O1 C1 C14 125.80(16) . . ? O1 C1 H1 117.1 . . ? C14 C1 H1 117.1 . . ? O2 C2 C21 109.30(11) . . ? O2 C2 H2A 109.8 . . ? C21 C2 H2A 109.8 . . ? O2 C2 H2B 109.8 . . ? C21 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? O2 C11 C12 124.18(12) . . ? O2 C11 C16 115.41(12) . . ? C12 C11 C16 120.41(13) . . ? C13 C12 C11 118.64(13) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C14 C13 C12 121.24(13) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.56(12) . . ? C13 C14 C1 118.50(13) . . ? C15 C14 C1 121.92(13) . . ? C16 C15 C14 119.93(13) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.21(13) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C22 C21 C26 118.96(13) . . ? C22 C21 C2 123.12(12) . . ? C26 C21 C2 117.90(13) . . ? C23 C22 C21 120.38(13) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 120.13(14) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C25 C24 C23 119.80(14) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 120.04(14) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.68(14) . . ? 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 O1 C1 1.206(2) . ? O2 C11 1.3597(16) . ? O2 C2 1.4294(17) . ? C1 C14 1.4686(19) . ? C1 H1 0.9500 . ? C2 C21 1.5031(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C11 C12 1.3916(19) . ? C11 C16 1.400(2) . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? C14 C15 1.396(2) . ? C15 C16 1.372(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.389(2) . ? C21 C26 1.391(2) . ? C22 C23 1.388(2) . ? C22 H22 0.9500 . ? C23 C24 1.388(2) . ? C23 H23 0.9500 . ? C24 C25 1.381(2) . ? C24 H24 0.9500 . ? C25 C26 1.386(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 C2 H2A O1 0.99 2.55 3.4988(19) 160 3_465 yes C2 H2B O1 0.99 2.51 3.343(2) 142 4_645 yes C22 H22 O2 0.95 2.41 2.7502(17) 101 . 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 -176.45(12) . . . . ? C2 O2 C11 C12 -6.2(2) . . . . ? C2 O2 C11 C16 174.25(14) . . . . ? O2 C11 C12 C13 -179.29(14) . . . . ? C16 C11 C12 C13 0.2(2) . . . . ? C11 C12 C13 C14 0.3(2) . . . . ? C12 C13 C14 C15 -0.8(2) . . . . ? C12 C13 C14 C1 177.97(15) . . . . ? O1 C1 C14 C13 -172.56(17) . . . . ? O1 C1 C14 C15 6.2(3) . . . . ? C13 C14 C15 C16 0.8(2) . . . . ? C1 C14 C15 C16 -177.91(15) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? O2 C11 C16 C15 179.35(15) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? O2 C2 C21 C22 10.15(19) . . . . ? O2 C2 C21 C26 -170.93(14) . . . . ? C26 C21 C22 C23 0.7(2) . . . . ? C2 C21 C22 C23 179.59(14) . . . . ? C21 C22 C23 C24 -0.4(2) . . . . ? C22 C23 C24 C25 -0.4(3) . . . . ? C23 C24 C25 C26 0.8(3) . . . . ? C24 C25 C26 C21 -0.4(3) . . . . ? C22 C21 C26 C25 -0.3(2) . . . . ? C2 C21 C26 C25 -179.25(15) . . . . ?