#------------------------------------------------------------------------------ #$Date: 2020-04-30 04:29:10 +0300 (Thu, 30 Apr 2020) $ #$Revision: 251301 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240424.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_7240424 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 'C16 H16 O3' _chemical_formula_sum 'C16 H16 O3' _chemical_formula_weight 256.29 _chemical_melting_point 352 _chemical_name_common 2-(benzyloxy)-3-ethoxybenzaldehyde _chemical_name_systematic 3-ethoxy-2-(phenylmethoxy)benzaldehyde _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 _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 99.697(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.3768(15) _cell_length_b 4.5578(5) _cell_length_c 19.4729(19) _cell_measurement_reflns_used 2176 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 22.85 _cell_measurement_theta_min 2.31 _cell_volume 1345.2(2) _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 0.997 _diffrn_measured_fraction_theta_max 0.992 _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 0.0644 _diffrn_reflns_av_unetI/netI 0.0671 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 12325 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.378 _diffrn_reflns_theta_min 2.122 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6753 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rods _exptl_crystal_F_000 544 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane' _exptl_crystal_size_max 0.629 _exptl_crystal_size_mid 0.092 _exptl_crystal_size_min 0.062 _refine_diff_density_max 0.427 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 3329 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.1308 _refine_ls_R_factor_gt 0.0625 _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^)+(0.0764P)^2^+0.2803P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1444 _refine_ls_wR_factor_ref 0.1769 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1762 _reflns_number_total 3329 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10752e2.cif _cod_data_source_block ia358 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240424 _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 0.948 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; TITL ia358_a.res in P2(1)/c ia358.res created by SHELXL-2018/3 at 12:28:55 on 01-Feb-2019 REM Old TITL ia358_s_P21c in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.207, Rweak 0.011, Alpha 0.033 REM 0.280 for 336 systematic absences, Orientation as input REM Formula found by SHELXT: C16 O3 CELL 0.71073 15.3768 4.5578 19.4729 90.000 99.697 90.000 ZERR 4.00 0.0015 0.0005 0.0019 0.000 0.005 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H O UNIT 64 64 12 OMIT 1 0 0 EQIV $1 1-x,-1/2+y,1/2-z HTAB C1 O2 HTAB C2 O3 HTAB C2 O1_$1 ACTA BOND $H CONF FMAP 2 HTAB L.S. 100 LIST 4 PLAN -20 SIZE 0.062 0.092 0.629 TEMP -73.140 REM WGHT 0.076400 0.280300 REM WGHT 0.076400 0.280300 REM WGHT 0.076400 0.280300 WGHT 0.076400 0.280300 FVAR 0.26068 O1 3 0.470716 0.762160 0.314996 11.00000 0.05376 0.08445 = 0.10292 -0.01543 -0.00242 0.02176 O2 3 0.724097 0.548565 0.316448 11.00000 0.05367 0.03002 = 0.03614 -0.00465 0.00909 -0.00128 O3 3 0.811471 0.152994 0.405074 11.00000 0.04453 0.03862 = 0.04567 0.00800 0.00596 -0.00055 C1 1 0.546819 0.697116 0.316540 11.00000 0.05058 0.05038 = 0.06604 -0.01855 -0.00050 0.00467 AFIX 43 H1 2 0.577619 0.784421 0.283384 11.00000 -1.20000 AFIX 0 C2 1 0.744130 0.364032 0.260515 11.00000 0.07380 0.03610 = 0.04036 -0.00599 0.01393 0.00477 AFIX 23 H2A 2 0.690802 0.256134 0.238458 11.00000 -1.20000 H2B 2 0.790519 0.219886 0.278628 11.00000 -1.20000 AFIX 0 C3 1 0.855146 -0.083603 0.445508 11.00000 0.05264 0.03931 = 0.04630 0.00587 -0.00427 -0.00295 AFIX 23 H3A 2 0.816769 -0.259318 0.441359 11.00000 -1.20000 H3B 2 0.869063 -0.027197 0.495245 11.00000 -1.20000 AFIX 0 C4 1 0.937975 -0.147486 0.417917 11.00000 0.06399 0.06476 = 0.06127 -0.00161 -0.00013 0.01699 AFIX 137 H4A 2 0.923359 -0.202572 0.368675 11.00000 -1.50000 H4B 2 0.969445 -0.309389 0.444390 11.00000 -1.50000 H4C 2 0.975527 0.027542 0.422563 11.00000 -1.50000 AFIX 0 C11 1 0.595064 0.487704 0.367517 11.00000 0.04223 0.04261 = 0.04822 -0.01672 0.00305 -0.00316 C12 1 0.681565 0.412341 0.364008 11.00000 0.04381 0.03017 = 0.03679 -0.00837 0.00606 -0.00698 C13 1 0.726682 0.210940 0.411830 11.00000 0.04128 0.03287 = 0.03878 -0.00618 0.00621 -0.00972 C14 1 0.684605 0.098305 0.463343 11.00000 0.05163 0.04577 = 0.04415 -0.00221 0.00841 -0.01368 AFIX 43 H14 2 0.714949 -0.035652 0.496347 11.00000 -1.20000 AFIX 0 C15 1 0.599446 0.177445 0.467479 11.00000 0.06035 0.06247 = 0.05143 -0.01033 0.01954 -0.02349 AFIX 43 H15 2 0.571580 0.098999 0.503427 11.00000 -1.20000 AFIX 0 C16 1 0.554290 0.369610 0.419875 11.00000 0.04138 0.06464 = 0.06360 -0.02669 0.01677 -0.01161 AFIX 43 H16 2 0.495193 0.421813 0.422730 11.00000 -1.20000 AFIX 0 C21 1 0.775487 0.563629 0.209012 11.00000 0.05169 0.03110 = 0.03592 -0.00910 0.00865 0.00091 C22 1 0.714798 0.701694 0.159760 11.00000 0.06922 0.03930 = 0.04090 -0.00427 0.00585 0.00084 AFIX 43 H22 2 0.653947 0.661079 0.158468 11.00000 -1.20000 AFIX 0 C23 1 0.738309 0.894601 0.112660 11.00000 0.11385 0.04907 = 0.04559 -0.00009 0.01325 0.00027 AFIX 43 H23 2 0.694473 0.987497 0.079570 11.00000 -1.20000 AFIX 0 C24 1 0.823602 0.951524 0.113549 11.00000 0.12717 0.05392 = 0.05526 -0.01396 0.03405 -0.01758 AFIX 43 H24 2 0.839725 1.087104 0.080829 11.00000 -1.20000 AFIX 0 C25 1 0.888400 0.820879 0.160041 11.00000 0.07613 0.07467 = 0.09140 -0.03819 0.04615 -0.03341 AFIX 43 H25 2 0.948821 0.861665 0.159296 11.00000 -1.20000 AFIX 0 C26 1 0.863350 0.621421 0.209854 11.00000 0.05907 0.06904 = 0.06078 -0.02439 0.00875 0.00181 AFIX 43 H26 2 0.907054 0.529601 0.243253 11.00000 -1.20000 AFIX 0 HKLF 4 REM ia358_a.res in P2(1)/c REM wR2 = 0.1769, GooF = S = 1.023, Restrained GooF = 1.023 for all data REM R1 = 0.0625 for 1762 Fo > 4sig(Fo) and 0.1308 for all 3329 data REM 173 parameters refined using 0 restraints END WGHT 0.0764 0.2803 REM Instructions for potential hydrogen bonds HTAB C2 O1_$1 HTAB C2 O3 REM Highest difference peak 0.427, deepest hole -0.219, 1-sigma level 0.050 Q1 1 0.9292 0.6620 0.1955 11.00000 0.05 0.43 Q2 1 0.8736 0.4874 0.2419 11.00000 0.05 0.28 Q3 1 0.4893 0.4358 0.3996 11.00000 0.05 0.20 Q4 1 0.6249 0.4369 0.3559 11.00000 0.05 0.19 Q5 1 0.6990 0.3025 0.3938 11.00000 0.05 0.17 Q6 1 0.7677 0.7318 0.1639 11.00000 0.05 0.16 Q7 1 0.9183 -0.0673 0.4505 11.00000 0.05 0.16 Q8 1 0.8813 0.9177 0.1698 11.00000 0.05 0.16 Q9 1 0.5839 0.4515 0.3910 11.00000 0.05 0.16 Q10 1 0.9065 0.9666 0.1073 11.00000 0.05 0.15 Q11 1 0.8832 0.8297 0.1311 11.00000 0.05 0.15 Q12 1 0.7937 0.8348 0.1311 11.00000 0.05 0.15 Q13 1 0.6479 0.3156 0.2377 11.00000 0.05 0.15 Q14 1 0.5689 0.5308 0.3423 11.00000 0.05 0.15 Q15 1 0.4557 0.5743 0.3603 11.00000 0.05 0.15 Q16 1 0.8037 0.5077 0.3163 11.00000 0.05 0.15 Q17 1 0.7623 0.2216 0.4100 11.00000 0.05 0.14 Q18 1 0.9150 0.8722 0.1468 11.00000 0.05 0.14 Q19 1 0.4142 0.3384 0.3847 11.00000 0.05 0.14 Q20 1 0.6111 0.6796 0.1656 11.00000 0.05 0.14 ; _shelx_res_checksum 85355 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 O1 O 0.47072(13) 0.7622(5) 0.31500(12) 0.0822(7) Uani 1 1 d . . . . . O2 O 0.72410(9) 0.5486(3) 0.31645(7) 0.0398(4) Uani 1 1 d . . . . . O3 O 0.81147(9) 0.1530(3) 0.40507(8) 0.0431(4) Uani 1 1 d . . . . . C1 C 0.54682(16) 0.6971(6) 0.31654(14) 0.0569(7) Uani 1 1 d . . . . . H1 H 0.577619 0.784421 0.283384 0.068 Uiso 1 1 calc R U . . . C2 C 0.74413(17) 0.3640(5) 0.26052(12) 0.0496(6) Uani 1 1 d . . . . . H2A H 0.690802 0.256134 0.238458 0.060 Uiso 1 1 calc R U . . . H2B H 0.790519 0.219886 0.278628 0.060 Uiso 1 1 calc R U . . . C3 C 0.85515(15) -0.0836(5) 0.44551(12) 0.0475(6) Uani 1 1 d . . . . . H3A H 0.816769 -0.259318 0.441359 0.057 Uiso 1 1 calc R U . . . H3B H 0.869063 -0.027197 0.495245 0.057 Uiso 1 1 calc R U . . . C4 C 0.93798(17) -0.1475(7) 0.41792(14) 0.0646(8) Uani 1 1 d . . . . . H4A H 0.923359 -0.202572 0.368675 0.097 Uiso 1 1 calc R U . . . H4B H 0.969445 -0.309389 0.444390 0.097 Uiso 1 1 calc R U . . . H4C H 0.975527 0.027542 0.422563 0.097 Uiso 1 1 calc R U . . . C11 C 0.59506(14) 0.4877(5) 0.36752(12) 0.0449(6) Uani 1 1 d . . . . . C12 C 0.68156(14) 0.4123(5) 0.36401(10) 0.0370(5) Uani 1 1 d . . . . . C13 C 0.72668(14) 0.2109(5) 0.41183(11) 0.0377(5) Uani 1 1 d . . . . . C14 C 0.68461(15) 0.0983(5) 0.46334(12) 0.0471(6) Uani 1 1 d . . . . . H14 H 0.714949 -0.035652 0.496347 0.057 Uiso 1 1 calc R U . . . C15 C 0.59945(17) 0.1774(6) 0.46748(13) 0.0569(7) Uani 1 1 d . . . . . H15 H 0.571580 0.098999 0.503427 0.068 Uiso 1 1 calc R U . . . C16 C 0.55429(16) 0.3696(6) 0.41987(14) 0.0556(7) Uani 1 1 d . . . . . H16 H 0.495193 0.421813 0.422730 0.067 Uiso 1 1 calc R U . . . C21 C 0.77549(14) 0.5636(5) 0.20901(10) 0.0394(5) Uani 1 1 d . . . . . C22 C 0.71480(17) 0.7017(5) 0.15976(12) 0.0502(6) Uani 1 1 d . . . . . H22 H 0.653947 0.661079 0.158468 0.060 Uiso 1 1 calc R U . . . C23 C 0.7383(3) 0.8946(6) 0.11266(14) 0.0695(8) Uani 1 1 d . . . . . H23 H 0.694473 0.987497 0.079570 0.083 Uiso 1 1 calc R U . . . C24 C 0.8236(3) 0.9515(7) 0.11355(15) 0.0766(9) Uani 1 1 d . . . . . H24 H 0.839725 1.087104 0.080829 0.092 Uiso 1 1 calc R U . . . C25 C 0.8884(2) 0.8209(8) 0.16004(19) 0.0770(10) Uani 1 1 d . . . . . H25 H 0.948821 0.861665 0.159296 0.092 Uiso 1 1 calc R U . . . C26 C 0.86335(18) 0.6214(7) 0.20985(14) 0.0631(8) Uani 1 1 d . . . . . H26 H 0.907054 0.529601 0.243253 0.076 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 0.0538(11) 0.0844(16) 0.1029(16) -0.0154(13) -0.0024(10) 0.0218(11) O2 0.0537(9) 0.0300(8) 0.0361(7) -0.0047(7) 0.0091(6) -0.0013(7) O3 0.0445(9) 0.0386(9) 0.0457(8) 0.0080(7) 0.0060(7) -0.0006(7) C1 0.0506(15) 0.0504(17) 0.0660(16) -0.0185(13) -0.0005(12) 0.0047(13) C2 0.0738(17) 0.0361(13) 0.0404(12) -0.0060(11) 0.0139(11) 0.0048(12) C3 0.0526(14) 0.0393(14) 0.0463(12) 0.0059(11) -0.0043(10) -0.0029(11) C4 0.0640(17) 0.0648(19) 0.0613(16) -0.0016(14) -0.0001(13) 0.0170(14) C11 0.0422(13) 0.0426(14) 0.0482(12) -0.0167(11) 0.0031(10) -0.0032(11) C12 0.0438(12) 0.0302(12) 0.0368(11) -0.0084(9) 0.0061(9) -0.0070(10) C13 0.0413(12) 0.0329(13) 0.0388(11) -0.0062(10) 0.0062(9) -0.0097(10) C14 0.0516(14) 0.0458(16) 0.0441(12) -0.0022(11) 0.0084(10) -0.0137(11) C15 0.0604(16) 0.0625(18) 0.0514(14) -0.0103(13) 0.0195(12) -0.0235(14) C16 0.0414(13) 0.0646(19) 0.0636(16) -0.0267(14) 0.0168(12) -0.0116(12) C21 0.0517(13) 0.0311(12) 0.0359(11) -0.0091(9) 0.0087(9) 0.0009(10) C22 0.0692(16) 0.0393(15) 0.0409(12) -0.0043(11) 0.0059(11) 0.0008(12) C23 0.114(3) 0.0491(19) 0.0456(14) -0.0001(13) 0.0132(15) 0.0003(17) C24 0.127(3) 0.054(2) 0.0553(17) -0.0140(15) 0.0340(19) -0.018(2) C25 0.076(2) 0.075(2) 0.091(2) -0.038(2) 0.0461(18) -0.0334(18) C26 0.0591(16) 0.069(2) 0.0608(16) -0.0244(15) 0.0088(13) 0.0018(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' 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 C12 O2 C2 115.55(16) . . ? C13 O3 C3 117.49(17) . . ? O1 C1 C11 123.4(3) . . ? O1 C1 H1 118.3 . . ? C11 C1 H1 118.3 . . ? O2 C2 C21 106.54(18) . . ? 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 . . ? O3 C3 C4 107.4(2) . . ? O3 C3 H3A 110.2 . . ? C4 C3 H3A 110.2 . . ? O3 C3 H3B 110.2 . . ? C4 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C12 C11 C16 119.6(2) . . ? C12 C11 C1 120.2(2) . . ? C16 C11 C1 120.2(2) . . ? O2 C12 C11 119.5(2) . . ? O2 C12 C13 120.39(19) . . ? C11 C12 C13 120.0(2) . . ? O3 C13 C14 125.0(2) . . ? O3 C13 C12 115.96(18) . . ? C14 C13 C12 119.0(2) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.1(2) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C22 C21 C26 118.2(2) . . ? C22 C21 C2 119.3(2) . . ? C26 C21 C2 122.5(2) . . ? C23 C22 C21 122.7(3) . . ? C23 C22 H22 118.7 . . ? C21 C22 H22 118.7 . . ? C24 C23 C22 119.2(3) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C25 122.0(3) . . ? C23 C24 H24 119.0 . . ? C25 C24 H24 119.0 . . ? C24 C25 C26 118.5(3) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C21 C26 C25 119.4(3) . . ? C21 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? 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 1.203(3) . ? O2 C12 1.369(2) . ? O2 C2 1.450(3) . ? O3 C13 1.358(2) . ? O3 C3 1.434(3) . ? C1 C11 1.483(4) . ? C1 H1 0.9500 . ? C2 C21 1.493(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.492(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C11 C12 1.387(3) . ? C11 C16 1.392(3) . ? C12 C13 1.405(3) . ? C13 C14 1.381(3) . ? C14 C15 1.374(3) . ? C14 H14 0.9500 . ? C15 C16 1.375(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.373(3) . ? C21 C26 1.374(3) . ? C22 C23 1.363(4) . ? C22 H22 0.9500 . ? C23 C24 1.334(4) . ? C23 H23 0.9500 . ? C24 C25 1.365(5) . ? C24 H24 0.9500 . ? C25 C26 1.429(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 2.48 2.809(3) 100 . yes C2 H2B O3 0.99 2.45 2.990(3) 114 . yes C2 H2A O1 0.99 2.53 3.414(3) 149 2_645 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 C12 O2 C2 C21 170.47(17) . . . . ? C13 O3 C3 C4 167.52(19) . . . . ? O1 C1 C11 C12 176.9(2) . . . . ? O1 C1 C11 C16 -4.3(4) . . . . ? C2 O2 C12 C11 -112.1(2) . . . . ? C2 O2 C12 C13 71.8(2) . . . . ? C16 C11 C12 O2 -174.17(19) . . . . ? C1 C11 C12 O2 4.7(3) . . . . ? C16 C11 C12 C13 1.9(3) . . . . ? C1 C11 C12 C13 -179.17(19) . . . . ? C3 O3 C13 C14 12.6(3) . . . . ? C3 O3 C13 C12 -170.55(17) . . . . ? O2 C12 C13 O3 -3.1(3) . . . . ? C11 C12 C13 O3 -179.18(18) . . . . ? O2 C12 C13 C14 173.91(18) . . . . ? C11 C12 C13 C14 -2.2(3) . . . . ? O3 C13 C14 C15 177.7(2) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? C14 C15 C16 C11 -0.7(4) . . . . ? C12 C11 C16 C15 -0.5(3) . . . . ? C1 C11 C16 C15 -179.4(2) . . . . ? O2 C2 C21 C22 -84.1(2) . . . . ? O2 C2 C21 C26 94.2(3) . . . . ? C26 C21 C22 C23 -0.8(3) . . . . ? C2 C21 C22 C23 177.6(2) . . . . ? C21 C22 C23 C24 0.6(4) . . . . ? C22 C23 C24 C25 0.4(4) . . . . ? C23 C24 C25 C26 -1.1(4) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? C2 C21 C26 C25 -178.4(2) . . . . ? C24 C25 C26 C21 0.9(4) . . . . ?