#------------------------------------------------------------------------------ #$Date: 2017-02-04 15:44:47 +0200 (Sat, 04 Feb 2017) $ #$Revision: 191570 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/73/7227365.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_7227365 loop_ _publ_author_name 'Sarmah, Kashyap Kumar' 'Boro, Kaveri' 'Arhangelskis, Mihails' 'Thakuria, Ranjit' _publ_section_title ; Crystal structure landscape of ethenzamide: a physicochemical property study ; _journal_issue 5 _journal_name_full CrystEngComm _journal_page_first 826 _journal_paper_doi 10.1039/C6CE02057G _journal_volume 19 _journal_year 2017 _chemical_formula_moiety 'C10 H10 O4, C9 H11 N O2' _chemical_formula_sum 'C19 H21 N O6' _chemical_formula_weight 359.37 _chemical_name_systematic 'Ethenzamide Ferulic acid' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2016-12-18 deposited with the CCDC. 2017-01-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.539(2) _cell_length_b 7.4265(10) _cell_length_c 31.796(4) _cell_measurement_reflns_used 2486 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 20.96 _cell_measurement_theta_min 2.56 _cell_volume 3669.3(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0754 _diffrn_reflns_av_unetI/netI 0.0514 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_number 28799 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.437 _diffrn_reflns_theta_min 1.281 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_correction_T_min 0.9742 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.301 _exptl_crystal_description needle _exptl_crystal_F_000 1520 _exptl_crystal_size_max 0.270 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.177 _refine_diff_density_min -0.211 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 3757 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all 0.1115 _refine_ls_R_factor_gt 0.0511 _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^)+(0.0783P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1342 _refine_ls_wR_factor_ref 0.1617 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2078 _reflns_number_total 3757 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce02057g2.cif _cod_data_source_block Ethenzamide-Ferulicacid _cod_depositor_comments 'Adding full bibliography for 7227362--7227365.cif.' _cod_original_cell_volume 3669.2(8) _cod_database_code 7227365 _shelx_shelxl_version_number 2016/6 _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 0.974 _shelx_estimated_absorpt_t_max 0.992 _exptl_absorpt_special_details 'Sheldrick,G.M.,2015,University of gottingen' _shelx_res_file ; TITL ortho in Pbca RT_ETZ_Ferulicacid.res created by SHELXL-2016/6 at 15:12:02 on 17-Dec-2016 CELL 0.71073 15.5386 7.4265 31.7961 90.000 90.000 90.000 ZERR 8.00 0.0021 0.0010 0.0038 0.000 0.000 0.000 LATT 1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O UNIT 152 168 8 48 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 12 ACTA EQIV $1 x-1/2, -y+3/2, -z+1 HTAB C17 O6_$1 HTAB N1 O2 EQIV $2 x, y+1, z HTAB O3 O1_$2 EQIV $3 x+1/2, -y+3/2, -z+1 HTAB O6 O4_$3 HTAB O6 O5 EQIV $4 x, y-1, z HTAB N1 O4_$4 BOND $H FMAP 2 PLAN 6 SIZE 0.08 0.10 0.27 TEMP 23.000 WGHT 0.078300 FVAR 0.07786 C1 1 0.283176 0.094750 0.264900 11.00000 0.04412 0.03972 = 0.04178 -0.00463 -0.00674 0.00132 C2 1 0.192975 0.092093 0.264403 11.00000 0.04542 0.04074 = 0.05288 -0.00587 -0.00854 -0.00089 C3 1 0.149309 0.147859 0.228738 11.00000 0.05283 0.05109 = 0.06617 -0.00744 -0.02113 0.00619 AFIX 43 H3 2 0.089469 0.146037 0.228342 11.00000 -1.20000 AFIX 0 C4 1 0.193686 0.205727 0.194014 11.00000 0.07876 0.04897 = 0.05603 -0.00101 -0.02292 0.00550 AFIX 43 H4 2 0.163551 0.242329 0.170233 11.00000 -1.20000 AFIX 0 C5 1 0.281759 0.210369 0.193866 11.00000 0.07405 0.05157 = 0.04452 0.00295 -0.00420 0.00018 AFIX 43 H5 2 0.311705 0.250369 0.170328 11.00000 -1.20000 AFIX 0 C6 1 0.324974 0.154589 0.229286 11.00000 0.05425 0.05013 = 0.04785 -0.00041 -0.00475 0.00175 AFIX 43 H6 2 0.384810 0.157331 0.229220 11.00000 -1.20000 AFIX 0 C7 1 0.338348 0.037396 0.300737 11.00000 0.04039 0.05050 = 0.04441 -0.00493 -0.00477 0.00177 C8 1 0.059575 0.035935 0.301680 11.00000 0.03852 0.07422 = 0.09383 -0.00570 -0.00481 -0.00205 AFIX 23 H8A 2 0.035336 -0.042093 0.280274 11.00000 -1.20000 H8B 2 0.038825 0.157430 0.296929 11.00000 -1.20000 AFIX 0 C9 1 0.033709 -0.027476 0.344418 11.00000 0.05383 0.09462 = 0.10441 -0.00394 0.02012 -0.00539 AFIX 137 H9A 2 0.051745 -0.150069 0.348161 11.00000 -1.50000 H9B 2 -0.027706 -0.020038 0.347202 11.00000 -1.50000 H9C 2 0.060461 0.046912 0.365365 11.00000 -1.50000 AFIX 0 C10 1 0.730795 0.899158 0.443330 11.00000 0.04375 0.03810 = 0.04145 0.00279 -0.00425 -0.00049 C11 1 0.714422 0.839271 0.484258 11.00000 0.03789 0.05310 = 0.04312 -0.00150 -0.00317 -0.00113 AFIX 43 H11 2 0.657935 0.823922 0.493236 11.00000 -1.20000 AFIX 0 C12 1 0.780625 0.803243 0.511080 11.00000 0.04905 0.05532 = 0.03862 0.00537 -0.00453 -0.00109 C13 1 0.865526 0.825494 0.498002 11.00000 0.04066 0.06981 = 0.05458 0.01051 -0.00949 0.00110 C14 1 0.882134 0.888492 0.458361 11.00000 0.03731 0.07276 = 0.06572 0.01508 0.00013 -0.00378 AFIX 43 H14 2 0.938639 0.907157 0.449759 11.00000 -1.20000 AFIX 0 C15 1 0.815158 0.924277 0.431187 11.00000 0.04709 0.05554 = 0.04408 0.00950 0.00148 -0.00277 AFIX 43 H15 2 0.827050 0.966031 0.404231 11.00000 -1.20000 AFIX 0 C16 1 0.660879 0.931027 0.413948 11.00000 0.04642 0.04536 = 0.03702 0.00313 -0.00199 -0.00155 AFIX 43 H16 2 0.675517 0.982338 0.388244 11.00000 -1.20000 AFIX 0 C17 1 0.578808 0.894633 0.420004 11.00000 0.04275 0.07263 = 0.04097 0.01570 -0.00261 -0.00107 AFIX 43 H17 2 0.563580 0.845411 0.445848 11.00000 -1.20000 AFIX 0 C18 1 0.510042 0.924619 0.389872 11.00000 0.04023 0.06056 = 0.04285 0.00707 -0.00042 0.00090 C19 1 0.688003 0.727507 0.568425 11.00000 0.06824 0.10457 = 0.04476 0.00956 0.00897 0.00782 AFIX 137 H19A 2 0.659257 0.841740 0.566890 11.00000 -1.50000 H19B 2 0.691101 0.689257 0.597226 11.00000 -1.50000 H19C 2 0.656530 0.640114 0.552352 11.00000 -1.50000 AFIX 0 H1A 2 0.251221 -0.022356 0.337554 11.00000 0.07989 H3A 2 0.488178 1.005374 0.337188 11.00000 0.10353 H6A 2 0.914504 0.750959 0.547109 11.00000 0.13640 H1B 2 0.337340 -0.047975 0.357901 11.00000 0.07536 N1 3 0.303161 -0.017373 0.336063 11.00000 0.04039 0.11167 = 0.04679 0.01838 -0.00374 -0.00194 O1 4 0.417865 0.041568 0.297027 11.00000 0.04013 0.09694 = 0.05202 0.01321 -0.00488 0.00219 O2 4 0.151979 0.031755 0.299790 11.00000 0.03694 0.07224 = 0.06341 0.00449 -0.00295 -0.00036 O3 4 0.534776 0.986291 0.353083 11.00000 0.03971 0.10325 = 0.04957 0.02578 -0.00507 -0.00619 O4 4 0.434807 0.891451 0.397714 11.00000 0.03759 0.10681 = 0.05182 0.02132 -0.00053 -0.00175 O5 4 0.772330 0.744352 0.551904 11.00000 0.05426 0.09424 = 0.04701 0.01555 -0.00595 0.00215 O6 4 0.932211 0.789418 0.524272 11.00000 0.04451 0.14165 = 0.07623 0.04223 -0.01783 -0.00324 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM ortho in Pbca REM R1 = 0.0511 for 2078 Fo > 4sig(Fo) and 0.1115 for all 3757 data REM 253 parameters refined using 0 restraints END WGHT 0.0783 0.0000 REM Highest difference peak 0.177, deepest hole -0.211, 1-sigma level 0.052 Q1 1 0.9402 1.0230 0.4568 11.00000 0.05 0.18 Q2 1 0.0800 -0.1386 0.3724 11.00000 0.05 0.17 Q3 1 1.0002 0.9446 0.4268 11.00000 0.05 0.17 Q4 1 0.8949 1.0855 0.4010 11.00000 0.05 0.17 Q5 1 0.0297 -0.1264 0.4030 11.00000 0.05 0.17 Q6 1 0.9612 0.9945 0.4034 11.00000 0.05 0.16 ; _shelx_res_checksum 45329 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -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 C1 C 0.28318(14) 0.0948(3) 0.26490(7) 0.0419(5) Uani 1 1 d . . C2 C 0.19297(15) 0.0921(3) 0.26440(8) 0.0463(6) Uani 1 1 d . . C3 C 0.14931(17) 0.1479(3) 0.22874(8) 0.0567(7) Uani 1 1 d . . H3 H 0.089469 0.146037 0.228342 0.068 Uiso 1 1 calc R U C4 C 0.19369(19) 0.2057(3) 0.19401(9) 0.0613(7) Uani 1 1 d . . H4 H 0.163551 0.242329 0.170233 0.074 Uiso 1 1 calc R U C5 C 0.28176(18) 0.2104(3) 0.19387(8) 0.0567(7) Uani 1 1 d . . H5 H 0.311705 0.250369 0.170328 0.068 Uiso 1 1 calc R U C6 C 0.32497(16) 0.1546(3) 0.22929(7) 0.0507(6) Uani 1 1 d . . H6 H 0.384810 0.157331 0.229220 0.061 Uiso 1 1 calc R U C7 C 0.33835(15) 0.0374(3) 0.30074(7) 0.0451(6) Uani 1 1 d . . C8 C 0.05958(16) 0.0359(4) 0.30168(10) 0.0689(8) Uani 1 1 d . . H8A H 0.035336 -0.042093 0.280274 0.083 Uiso 1 1 calc R U H8B H 0.038825 0.157430 0.296929 0.083 Uiso 1 1 calc R U C9 C 0.03371(18) -0.0275(4) 0.34442(11) 0.0843(10) Uani 1 1 d . . H9A H 0.051745 -0.150069 0.348161 0.126 Uiso 1 1 calc R U H9B H -0.027706 -0.020038 0.347202 0.126 Uiso 1 1 calc R U H9C H 0.060461 0.046912 0.365365 0.126 Uiso 1 1 calc R U C10 C 0.73079(14) 0.8992(3) 0.44333(7) 0.0411(6) Uani 1 1 d . . C11 C 0.71442(14) 0.8393(3) 0.48426(7) 0.0447(6) Uani 1 1 d . . H11 H 0.657935 0.823922 0.493236 0.054 Uiso 1 1 calc R U C12 C 0.78062(14) 0.8032(3) 0.51108(7) 0.0477(6) Uani 1 1 d . . C13 C 0.86553(14) 0.8255(4) 0.49800(8) 0.0550(7) Uani 1 1 d . . C14 C 0.88213(15) 0.8885(4) 0.45836(8) 0.0586(7) Uani 1 1 d . . H14 H 0.938639 0.907157 0.449759 0.070 Uiso 1 1 calc R U C15 C 0.81516(15) 0.9243(3) 0.43119(7) 0.0489(6) Uani 1 1 d . . H15 H 0.827050 0.966031 0.404231 0.059 Uiso 1 1 calc R U C16 C 0.66088(14) 0.9310(3) 0.41395(7) 0.0429(6) Uani 1 1 d . . H16 H 0.675517 0.982338 0.388244 0.052 Uiso 1 1 calc R U C17 C 0.57881(15) 0.8946(4) 0.42000(7) 0.0521(6) Uani 1 1 d . . H17 H 0.563580 0.845411 0.445848 0.063 Uiso 1 1 calc R U C18 C 0.51004(15) 0.9246(3) 0.38987(7) 0.0479(6) Uani 1 1 d . . C19 C 0.68800(18) 0.7275(5) 0.56843(8) 0.0725(8) Uani 1 1 d . . H19A H 0.659257 0.841740 0.566890 0.109 Uiso 1 1 calc R U H19B H 0.691101 0.689257 0.597226 0.109 Uiso 1 1 calc R U H19C H 0.656530 0.640114 0.552352 0.109 Uiso 1 1 calc R U H1A H 0.251(2) -0.022(4) 0.3376(9) 0.080(10) Uiso 1 1 d . . H3A H 0.488(2) 1.005(4) 0.3372(11) 0.104(11) Uiso 1 1 d . . H6A H 0.915(3) 0.751(6) 0.5471(14) 0.136(17) Uiso 1 1 d . . H1B H 0.3373(19) -0.048(4) 0.3579(9) 0.075(9) Uiso 1 1 d . . N1 N 0.30316(17) -0.0174(4) 0.33606(7) 0.0663(7) Uani 1 1 d . . O1 O 0.41786(10) 0.0416(3) 0.29703(5) 0.0630(5) Uani 1 1 d . . O2 O 0.15198(10) 0.0318(2) 0.29979(5) 0.0575(5) Uani 1 1 d . . O3 O 0.53478(11) 0.9863(3) 0.35308(6) 0.0642(6) Uani 1 1 d . . O4 O 0.43481(10) 0.8915(3) 0.39771(5) 0.0654(6) Uani 1 1 d . . O5 O 0.77233(11) 0.7444(3) 0.55190(5) 0.0652(5) Uani 1 1 d . . O6 O 0.93221(12) 0.7894(3) 0.52427(8) 0.0875(8) Uani 1 1 d . . 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 C1 0.0441(13) 0.0397(12) 0.0418(13) -0.0046(11) -0.0067(10) 0.0013(10) C2 0.0454(14) 0.0407(13) 0.0529(15) -0.0059(12) -0.0085(11) -0.0009(11) C3 0.0528(15) 0.0511(15) 0.0662(18) -0.0074(14) -0.0211(13) 0.0062(12) C4 0.079(2) 0.0490(16) 0.0560(17) -0.0010(13) -0.0229(15) 0.0055(14) C5 0.0741(19) 0.0516(15) 0.0445(15) 0.0030(12) -0.0042(13) 0.0002(13) C6 0.0543(15) 0.0501(14) 0.0479(15) -0.0004(12) -0.0048(12) 0.0018(11) C7 0.0404(14) 0.0505(14) 0.0444(14) -0.0049(12) -0.0048(11) 0.0018(10) C8 0.0385(14) 0.0742(19) 0.094(2) -0.0057(17) -0.0048(14) -0.0020(12) C9 0.0538(18) 0.095(2) 0.104(3) -0.004(2) 0.0201(16) -0.0054(16) C10 0.0438(13) 0.0381(12) 0.0415(14) 0.0028(11) -0.0043(10) -0.0005(10) C11 0.0379(12) 0.0531(14) 0.0431(14) -0.0015(12) -0.0032(10) -0.0011(10) C12 0.0490(14) 0.0553(16) 0.0386(14) 0.0054(12) -0.0045(10) -0.0011(11) C13 0.0407(13) 0.0698(17) 0.0546(16) 0.0105(13) -0.0095(11) 0.0011(12) C14 0.0373(13) 0.0728(18) 0.0657(18) 0.0151(15) 0.0001(12) -0.0038(12) C15 0.0471(14) 0.0555(15) 0.0441(14) 0.0095(12) 0.0015(11) -0.0028(11) C16 0.0464(14) 0.0454(13) 0.0370(13) 0.0031(11) -0.0020(10) -0.0016(10) C17 0.0428(14) 0.0726(17) 0.0410(14) 0.0157(13) -0.0026(10) -0.0011(12) C18 0.0402(14) 0.0606(16) 0.0428(15) 0.0071(12) -0.0004(10) 0.0009(11) C19 0.068(2) 0.105(2) 0.0448(16) 0.0096(16) 0.0090(13) 0.0078(16) N1 0.0404(14) 0.112(2) 0.0468(15) 0.0184(13) -0.0037(12) -0.0019(13) O1 0.0401(10) 0.0969(14) 0.0520(11) 0.0132(10) -0.0049(8) 0.0022(9) O2 0.0369(9) 0.0722(12) 0.0634(11) 0.0045(9) -0.0029(8) -0.0004(8) O3 0.0397(10) 0.1033(15) 0.0496(11) 0.0258(10) -0.0051(8) -0.0062(9) O4 0.0376(10) 0.1068(15) 0.0518(11) 0.0213(10) -0.0005(8) -0.0018(9) O5 0.0543(11) 0.0942(14) 0.0470(11) 0.0156(10) -0.0059(8) 0.0021(9) O6 0.0445(11) 0.142(2) 0.0762(16) 0.0422(15) -0.0178(10) -0.0032(11) 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' N N 0.0061 0.0033 '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 C6 C1 C2 117.8(2) C6 C1 C7 116.7(2) C2 C1 C7 125.5(2) O2 C2 C3 122.9(2) O2 C2 C1 117.4(2) C3 C2 C1 119.7(2) C4 C3 C2 120.5(3) C4 C3 H3 119.8 C2 C3 H3 119.8 C5 C4 C3 120.9(2) C5 C4 H4 119.6 C3 C4 H4 119.6 C4 C5 C6 118.5(2) C4 C5 H5 120.7 C6 C5 H5 120.7 C5 C6 C1 122.7(2) C5 C6 H6 118.7 C1 C6 H6 118.7 O1 C7 N1 120.2(2) O1 C7 C1 119.6(2) N1 C7 C1 120.2(2) O2 C8 C9 107.5(2) O2 C8 H8A 110.2 C9 C8 H8A 110.2 O2 C8 H8B 110.2 C9 C8 H8B 110.2 H8A C8 H8B 108.5 C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C15 C10 C11 118.4(2) C15 C10 C16 120.6(2) C11 C10 C16 121.0(2) C12 C11 C10 120.5(2) C12 C11 H11 119.8 C10 C11 H11 119.8 C11 C12 O5 125.6(2) C11 C12 C13 120.3(2) O5 C12 C13 114.1(2) O6 C13 C14 119.3(2) O6 C13 C12 121.0(2) C14 C13 C12 119.6(2) C13 C14 C15 120.0(2) C13 C14 H14 120.0 C15 C14 H14 120.0 C14 C15 C10 121.1(2) C14 C15 H15 119.5 C10 C15 H15 119.5 C17 C16 C10 126.6(2) C17 C16 H16 116.7 C10 C16 H16 116.7 C16 C17 C18 125.7(2) C16 C17 H17 117.1 C18 C17 H17 117.1 O4 C18 O3 122.2(2) O4 C18 C17 122.6(2) O3 C18 C17 115.2(2) O5 C19 H19A 109.5 O5 C19 H19B 109.5 H19A C19 H19B 109.5 O5 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C7 N1 H1A 119(2) C7 N1 H1B 119.4(18) H1A N1 H1B 122(3) C2 O2 C8 119.5(2) C18 O3 H3A 109(2) C12 O5 C19 117.67(19) C13 O6 H6A 111(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C6 1.379(3) C1 C2 1.402(3) C1 C7 1.488(3) C2 O2 1.368(3) C2 C3 1.385(3) C3 C4 1.371(4) C3 H3 0.9300 C4 C5 1.369(4) C4 H4 0.9300 C5 C6 1.375(3) C5 H5 0.9300 C6 H6 0.9300 C7 O1 1.242(3) C7 N1 1.314(3) C8 O2 1.437(3) C8 C9 1.493(4) C8 H8A 0.9700 C8 H8B 0.9700 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C10 C15 1.379(3) C10 C11 1.399(3) C10 C16 1.452(3) C11 C12 1.363(3) C11 H11 0.9300 C12 O5 1.376(3) C12 C13 1.393(3) C13 O6 1.358(3) C13 C14 1.369(3) C14 C15 1.379(3) C14 H14 0.9300 C15 H15 0.9300 C16 C17 1.318(3) C16 H16 0.9300 C17 C18 1.452(3) C17 H17 0.9300 C18 O4 1.220(3) C18 O3 1.314(3) C19 O5 1.417(3) C19 H19A 0.9600 C19 H19B 0.9600 C19 H19C 0.9600 N1 H1A 0.81(3) N1 H1B 0.90(3) O3 H3A 0.89(4) O6 H6A 0.83(4) 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 C17 H17 O6 0.93 2.46 3.193(3) 135.3 2_466 N1 H1A O2 0.81(3) 2.00(3) 2.642(3) 137(3) . O3 H3A O1 0.89(4) 1.70(4) 2.578(2) 166(3) 1_565 O6 H6A O4 0.83(4) 2.07(4) 2.821(3) 150(4) 2_566 O6 H6A O5 0.83(4) 2.21(4) 2.656(3) 114(4) . N1 H1B O4 0.90(3) 2.02(3) 2.913(3) 168(2) 1_545