#------------------------------------------------------------------------------ #$Date: 2017-07-25 07:12:37 +0300 (Tue, 25 Jul 2017) $ #$Revision: 199012 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/87/7228731.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_7228731 loop_ _publ_author_name 'De Rosa, Margherita' 'La Manna, Pellegrino' 'Soriente, Annunziata' 'Gaeta, Carmine' 'Talotta, Carmen' 'Hickey, Neal' 'Geremia, Silvano' 'Neri, Placido' _publ_section_title ; Supramolecular Synthons in the Gamma-Hydroxybutenolides ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE00953D _journal_year 2017 _chemical_absolute_configuration ad _chemical_formula_moiety 'C15 H13 N O5' _chemical_formula_sum 'C15 H13 N O5' _chemical_formula_weight 287.26 _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P -2ac -2n' _symmetry_space_group_name_H-M 'P n 21 a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary direct _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4.3 _audit_creation_date 2016-12-20T14:37:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2017-06-26 deposited with the CCDC. 2017-07-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2780(3) _cell_length_b 10.4130(16) _cell_length_c 12.4050(11) _cell_measurement_reflns_used 2854 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.983 _cell_measurement_theta_min 2.515 _cell_measurement_wavelength 0.7 _cell_volume 1327.6(2) _computing_cell_refinement XDS _computing_data_collection 'ELETTRA XRD1 Data Collectuion SW' _computing_data_reduction 'XDS - CCP4' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)' _computing_publication_material 'WinGX publication routines (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SIR-2014 (Burla et al., 2014)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measurement_device 'Area Detector' _diffrn_measurement_device_type 'Dectris Pilatus 2M' _diffrn_measurement_method 'Rotating crystal' _diffrn_radiation_probe x-ray _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.7 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_unetI/netI 0.0172 _diffrn_reflns_Laue_measured_fraction_full 0.972 _diffrn_reflns_Laue_measured_fraction_max 0.963 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 24594 _diffrn_reflns_point_group_measured_fraction_full 0.975 _diffrn_reflns_point_group_measured_fraction_max 0.966 _diffrn_reflns_theta_full 24.835 _diffrn_reflns_theta_max 29.983 _diffrn_reflns_theta_min 2.515 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.295 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; Flack x determined using 1858 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.03(9) _refine_ls_extinction_coef 0.197(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 193 _refine_ls_number_reflns 3912 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0277 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.2492P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.0764 _reflns_Friedel_coverage 0.911 _reflns_Friedel_fraction_full 0.978 _reflns_Friedel_fraction_max 0.97 _reflns_number_gt 3904 _reflns_number_total 3912 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce00953d2.cif _cod_data_source_block shelx_CCDC1 _cod_original_sg_symbol_H-M Pn21a _cod_database_code 7228731 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR2014 run in space group P n 21 a CELL 0.70000 10.2780 10.4130 12.4050 90.000 90.000 90.000 ZERR 4.00 0.0003 0.0016 0.0011 0.000 0.000 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SYMM 1/2 - X, 1/2 + Y, 1/2 + Z SYMM 1/2 + X, Y, 1/2 - Z SFAC C H N O DISP C 0.00299 0.00157 10.98 DISP H 0.00000 0.00000 0.67 DISP N 0.00588 0.00321 18.71 DISP O 0.01046 0.00590 30.82 UNIT 60 52 4 20 MERG 2 OMIT 1 0 1 OMIT 2 -1 1 OMIT 0 -3 1 OMIT 3 1 1 OMIT 1 2 2 OMIT 2 -1 0 OMIT 0 -1 3 OMIT 0 0 4 OMIT 2 1 1 OMIT 1 -2 2 OMIT 4 2 0 OMIT 2 -2 2 OMIT 6 0 0 OMIT 2 -2 0 OMIT 5 0 1 OMIT 1 1 1 OMIT 0 2 4 OMIT 5 1 1 OMIT 4 0 1 OMIT 0 -4 0 FMAP 2 PLAN 25 ACTA BOND $H CONF L.S. 10 TEMP -173.00 WGHT 0.047200 0.249200 EXTI 0.196627 FVAR 11.58498 C1 1 0.579777 1.026448 0.804122 11.00000 0.02482 0.03214 = 0.02133 0.00091 -0.00491 -0.00371 AFIX 137 H1A 2 0.646662 0.968235 0.776154 11.00000 -1.50000 H1B 2 0.579332 1.022841 0.883064 11.00000 -1.50000 H1C 2 0.598716 1.114354 0.780673 11.00000 -1.50000 AFIX 0 C2 1 0.449094 0.986521 0.761994 11.00000 0.02177 0.03268 = 0.01217 -0.00151 0.00133 -0.00339 AFIX 23 H2A 2 0.422268 0.905073 0.796646 11.00000 -1.20000 H2B 2 0.383700 1.052936 0.780031 11.00000 -1.20000 AFIX 0 C3 1 0.424355 1.070424 0.583226 11.00000 0.00993 0.01829 = 0.01546 -0.00315 0.00228 -0.00243 C4 1 0.447802 1.041252 0.462332 11.00000 0.00845 0.01307 = 0.01368 -0.00084 0.00033 0.00041 C5 1 0.399705 0.904570 0.436571 11.00000 0.00854 0.01438 = 0.01256 -0.00134 0.00041 -0.00128 AFIX 13 H5 2 0.455426 0.839928 0.474289 11.00000 -1.20000 AFIX 0 C6 1 0.393101 0.874303 0.318761 11.00000 0.01614 0.01713 = 0.01306 -0.00300 0.00156 -0.00037 AFIX 43 H6 2 0.464472 0.877203 0.270160 11.00000 -1.20000 AFIX 0 C7 1 0.271352 0.842615 0.292642 11.00000 0.01792 0.01985 = 0.01411 -0.00334 -0.00216 -0.00150 AFIX 43 H7 2 0.242045 0.818329 0.222931 11.00000 -1.20000 AFIX 0 C8 1 0.190081 0.851626 0.390062 11.00000 0.01351 0.01512 = 0.01711 -0.00033 -0.00242 -0.00146 C9 1 0.594098 1.052707 0.441202 11.00000 0.00909 0.01456 = 0.01166 -0.00254 -0.00017 -0.00031 C10 1 0.638752 1.152188 0.375525 11.00000 0.01162 0.01523 = 0.01674 0.00055 0.00042 0.00068 AFIX 43 H10 2 0.578137 1.207135 0.340667 11.00000 -1.20000 AFIX 0 C11 1 0.771030 1.171283 0.360859 11.00000 0.01311 0.01738 = 0.01896 0.00161 0.00238 -0.00022 AFIX 43 H11 2 0.801001 1.239279 0.316245 11.00000 -1.20000 AFIX 0 C12 1 0.859680 1.090684 0.411601 11.00000 0.00965 0.01921 = 0.01551 -0.00216 0.00136 -0.00070 C13 1 0.816531 0.986351 0.473251 11.00000 0.01098 0.02068 = 0.01545 0.00090 -0.00027 0.00130 AFIX 43 H13 2 0.877414 0.928693 0.504518 11.00000 -1.20000 AFIX 0 C14 1 0.683806 0.967945 0.488264 11.00000 0.01110 0.01773 = 0.01521 0.00125 0.00002 0.00030 AFIX 43 H14 2 0.653752 0.897839 0.530472 11.00000 -1.20000 AFIX 0 C15 1 0.996664 1.119139 0.403061 11.00000 0.01302 0.02166 = 0.01878 0.00015 0.00094 0.00051 N1 3 1.104545 1.146091 0.397882 11.00000 0.01318 0.02764 = 0.02775 0.00337 0.00206 0.00029 O1 4 0.454420 0.969239 0.645133 11.00000 0.02225 0.02204 = 0.01180 -0.00168 0.00011 0.00096 O2 4 0.386738 1.172159 0.615737 11.00000 0.02624 0.02079 = 0.02448 -0.00584 0.00709 0.00227 O3 4 0.384043 1.133508 0.399070 11.00000 0.00841 0.01664 = 0.02215 0.00385 -0.00036 0.00110 AFIX 147 H1O3 2 0.303563 1.129610 0.410394 11.00000 -1.50000 AFIX 0 O4 4 0.266683 0.893539 0.473208 11.00000 0.00890 0.01798 = 0.01341 -0.00077 0.00102 -0.00233 O5 4 0.076396 0.828086 0.403392 11.00000 0.01217 0.02444 = 0.02797 -0.00048 -0.00192 -0.00429 HKLF 4 REM SIR2014 run in space group P n 21 a REM R1 = 0.0277 for 3904 Fo > 4sig(Fo) and 0.0278 for all 3912 data REM 193 parameters refined using 1 restraints END WGHT 0.0474 0.2471 REM Highest difference peak 0.295, deepest hole -0.191, 1-sigma level 0.044 Q1 1 0.4255 0.9738 0.4498 11.00000 0.05 0.30 Q2 1 0.8145 1.1300 0.3874 11.00000 0.05 0.29 Q3 1 0.5244 1.0465 0.4509 11.00000 0.05 0.28 Q4 1 0.7047 1.1629 0.3688 11.00000 0.05 0.28 Q5 1 0.4780 1.0302 0.6320 11.00000 0.05 0.26 Q6 1 0.4588 1.0618 0.7605 11.00000 0.05 0.25 Q7 1 0.8398 1.0458 0.4428 11.00000 0.05 0.24 Q8 1 0.2297 0.8477 0.3398 11.00000 0.05 0.23 Q9 1 0.3267 0.8875 0.3011 11.00000 0.05 0.23 Q10 1 0.4339 1.0553 0.5217 11.00000 0.05 0.23 Q11 1 0.9222 1.1049 0.4016 11.00000 0.05 0.22 Q12 1 0.3990 0.8967 0.3752 11.00000 0.05 0.21 Q13 1 0.7442 0.9746 0.4731 11.00000 0.05 0.21 Q14 1 0.6381 1.0167 0.4673 11.00000 0.05 0.20 Q15 1 0.3403 1.1986 0.5767 11.00000 0.05 0.20 Q16 1 0.6174 1.1160 0.4172 11.00000 0.05 0.20 Q17 1 0.5194 1.0013 0.7851 11.00000 0.05 0.19 Q18 1 1.0231 1.1561 0.3810 11.00000 0.05 0.17 Q19 1 0.5338 0.9727 0.7934 11.00000 0.05 0.17 Q20 1 0.3257 0.9131 0.4547 11.00000 0.05 0.16 Q21 1 0.4363 0.8792 0.7693 11.00000 0.05 0.14 Q22 1 0.4160 1.0809 0.4223 11.00000 0.05 0.13 Q23 1 0.2252 0.8834 0.4348 11.00000 0.05 0.13 Q24 1 0.4427 0.9828 0.7009 11.00000 0.05 0.13 Q25 1 0.2796 0.9811 0.6203 11.00000 0.05 0.12 ; _shelx_res_checksum 96483 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x+1/2, 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 0.57978(16) 1.02645(17) 0.80412(13) 0.0261(3) Uani 1 1 d . . H1A H 0.6467 0.9682 0.7762 0.039 Uiso 1 1 calc R U H1B H 0.5793 1.0228 0.8831 0.039 Uiso 1 1 calc R U H1C H 0.5987 1.1144 0.7807 0.039 Uiso 1 1 calc R U C2 C 0.44909(15) 0.98652(16) 0.76199(11) 0.0222(3) Uani 1 1 d . . H2A H 0.4223 0.9051 0.7966 0.027 Uiso 1 1 calc R U H2B H 0.3837 1.0529 0.78 0.027 Uiso 1 1 calc R U C3 C 0.42436(12) 1.07042(13) 0.58323(10) 0.0146(2) Uani 1 1 d . . C4 C 0.44780(11) 1.04125(12) 0.46233(10) 0.0117(2) Uani 1 1 d . . C5 C 0.39970(12) 0.90457(12) 0.43657(10) 0.0118(2) Uani 1 1 d . . H5 H 0.4554 0.8399 0.4743 0.014 Uiso 1 1 calc R U C6 C 0.39310(13) 0.87430(13) 0.31876(11) 0.0154(2) Uani 1 1 d . . H6 H 0.4645 0.8772 0.2702 0.019 Uiso 1 1 calc R U C7 C 0.27135(14) 0.84261(14) 0.29264(10) 0.0173(2) Uani 1 1 d . . H7 H 0.242 0.8183 0.2229 0.021 Uiso 1 1 calc R U C8 C 0.19008(13) 0.85163(12) 0.39006(10) 0.0152(2) Uani 1 1 d . . C9 C 0.59410(12) 1.05271(12) 0.44120(9) 0.0118(2) Uani 1 1 d . . C10 C 0.63875(13) 1.15219(13) 0.37552(10) 0.0145(2) Uani 1 1 d . . H10 H 0.5781 1.2071 0.3407 0.017 Uiso 1 1 calc R U C11 C 0.77103(13) 1.17128(13) 0.36086(11) 0.0165(2) Uani 1 1 d . . H11 H 0.801 1.2393 0.3162 0.02 Uiso 1 1 calc R U C12 C 0.85968(13) 1.09068(12) 0.41160(10) 0.0148(2) Uani 1 1 d . . C13 C 0.81653(13) 0.98635(13) 0.47325(10) 0.0157(2) Uani 1 1 d . . H13 H 0.8774 0.9287 0.5045 0.019 Uiso 1 1 calc R U C14 C 0.68381(13) 0.96795(13) 0.48826(10) 0.0147(2) Uani 1 1 d . . H14 H 0.6538 0.8978 0.5305 0.018 Uiso 1 1 calc R U C15 C 0.99666(14) 1.11914(15) 0.40306(11) 0.0178(3) Uani 1 1 d . . N1 N 1.10454(13) 1.14609(14) 0.39788(11) 0.0229(3) Uani 1 1 d . . O1 O 0.45442(11) 0.96924(11) 0.64513(8) 0.0187(2) Uani 1 1 d . . O2 O 0.38674(12) 1.17216(11) 0.61574(9) 0.0238(2) Uani 1 1 d . . O3 O 0.38404(9) 1.13351(10) 0.39907(8) 0.0157(2) Uani 1 1 d . . H1O3 H 0.3036 1.1296 0.4104 0.024 Uiso 1 1 calc R U O4 O 0.26668(9) 0.89354(9) 0.47321(8) 0.01343(19) Uani 1 1 d . . O5 O 0.07640(11) 0.82809(11) 0.40339(9) 0.0215(2) 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 0.0248(7) 0.0321(8) 0.0213(6) 0.0009(5) -0.0049(5) -0.0037(6) C2 0.0218(7) 0.0327(7) 0.0122(5) -0.0015(5) 0.0013(4) -0.0034(5) C3 0.0099(5) 0.0183(6) 0.0155(5) -0.0032(4) 0.0023(4) -0.0024(4) C4 0.0084(5) 0.0131(5) 0.0137(5) -0.0008(4) 0.0003(4) 0.0004(4) C5 0.0085(5) 0.0144(5) 0.0126(5) -0.0013(4) 0.0004(4) -0.0013(4) C6 0.0161(6) 0.0171(5) 0.0131(5) -0.0030(4) 0.0016(4) -0.0004(4) C7 0.0179(6) 0.0198(6) 0.0141(5) -0.0033(4) -0.0022(4) -0.0015(5) C8 0.0135(6) 0.0151(5) 0.0171(5) -0.0003(4) -0.0024(4) -0.0015(4) C9 0.0091(5) 0.0146(5) 0.0117(5) -0.0025(4) -0.0002(4) -0.0003(4) C10 0.0116(6) 0.0152(5) 0.0167(5) 0.0005(4) 0.0004(4) 0.0007(4) C11 0.0131(6) 0.0174(5) 0.0190(5) 0.0016(4) 0.0024(4) -0.0002(4) C12 0.0096(6) 0.0192(6) 0.0155(5) -0.0022(4) 0.0014(4) -0.0007(4) C13 0.0110(6) 0.0207(6) 0.0154(5) 0.0009(4) -0.0003(4) 0.0013(4) C14 0.0111(6) 0.0177(5) 0.0152(5) 0.0013(4) 0.0000(4) 0.0003(4) C15 0.0130(6) 0.0217(6) 0.0188(6) 0.0001(4) 0.0009(4) 0.0005(5) N1 0.0132(6) 0.0276(6) 0.0278(6) 0.0034(5) 0.0021(4) 0.0003(4) O1 0.0222(5) 0.0220(4) 0.0118(4) -0.0017(3) 0.0001(3) 0.0010(4) O2 0.0262(6) 0.0208(5) 0.0245(5) -0.0058(4) 0.0071(4) 0.0023(4) O3 0.0084(4) 0.0166(4) 0.0221(4) 0.0038(3) -0.0004(3) 0.0011(3) O4 0.0089(4) 0.0180(4) 0.0134(4) -0.0008(3) 0.0010(3) -0.0023(3) O5 0.0122(5) 0.0244(5) 0.0280(5) -0.0005(4) -0.0019(4) -0.0043(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0105 0.0059 '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 C2 C1 H1A 109.5 C2 C1 H1B 109.5 H1A C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 O1 C2 C1 110.25(12) O1 C2 H2A 109.6 C1 C2 H2A 109.6 O1 C2 H2B 109.6 C1 C2 H2B 109.6 H2A C2 H2B 108.1 O2 C3 O1 125.24(13) O2 C3 C4 123.35(13) O1 C3 C4 111.40(11) O3 C4 C9 108.04(10) O3 C4 C5 111.52(10) C9 C4 C5 110.59(10) O3 C4 C3 109.55(10) C9 C4 C3 107.65(9) C5 C4 C3 109.40(10) O4 C5 C6 104.33(10) O4 C5 C4 108.17(10) C6 C5 C4 114.32(10) O4 C5 H5 109.9 C6 C5 H5 109.9 C4 C5 H5 109.9 C7 C6 C5 109.38(11) C7 C6 H6 125.3 C5 C6 H6 125.3 C6 C7 C8 108.49(11) C6 C7 H7 125.8 C8 C7 H7 125.8 O5 C8 O4 121.27(12) O5 C8 C7 130.52(12) O4 C8 C7 108.21(11) C10 C9 C14 119.58(12) C10 C9 C4 118.74(11) C14 C9 C4 121.67(11) C11 C10 C9 120.38(12) C11 C10 H10 119.8 C9 C10 H10 119.8 C10 C11 C12 119.81(12) C10 C11 H11 120.1 C12 C11 H11 120.1 C11 C12 C13 120.55(12) C11 C12 C15 118.86(12) C13 C12 C15 120.56(12) C14 C13 C12 119.39(12) C14 C13 H13 120.3 C12 C13 H13 120.3 C13 C14 C9 120.15(11) C13 C14 H14 119.9 C9 C14 H14 119.9 N1 C15 C12 177.48(16) C3 O1 C2 117.58(11) C4 O3 H1O3 109.5 C8 O4 C5 109.42(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.500(2) C1 H1A 0.98 C1 H1B 0.98 C1 H1C 0.98 C2 O1 1.4618(15) C2 H2A 0.99 C2 H2B 0.99 C3 O2 1.1977(17) C3 O1 1.3399(17) C3 C4 1.5490(17) C4 O3 1.4029(15) C4 C9 1.5310(16) C4 C5 1.5402(17) C5 O4 1.4453(15) C5 C6 1.4966(17) C5 H5 1 C6 C7 1.3340(19) C6 H6 0.95 C7 C8 1.4721(18) C7 H7 0.95 C8 O5 1.2053(18) C8 O4 1.3690(15) C9 C10 1.3955(17) C9 C14 1.4036(17) C10 C11 1.3860(18) C10 H10 0.95 C11 C12 1.3895(18) C11 H11 0.95 C12 C13 1.4007(18) C12 C15 1.4427(18) C13 C14 1.3901(18) C13 H13 0.95 C14 H14 0.95 C15 N1 1.146(2) O3 H1O3 0.84 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 O2 C3 C4 O3 -17.18(18) O1 C3 C4 O3 164.31(11) O2 C3 C4 C9 100.06(15) O1 C3 C4 C9 -78.44(13) O2 C3 C4 C5 -139.71(13) O1 C3 C4 C5 41.78(14) O3 C4 C5 O4 -68.36(12) C9 C4 C5 O4 171.39(9) C3 C4 C5 O4 52.98(12) O3 C4 C5 C6 47.36(14) C9 C4 C5 C6 -72.88(13) C3 C4 C5 C6 168.71(10) O4 C5 C6 C7 -3.11(15) C4 C5 C6 C7 -121.05(13) C5 C6 C7 C8 0.82(16) C6 C7 C8 O5 -177.60(15) C6 C7 C8 O4 1.96(16) O3 C4 C9 C10 5.33(15) C5 C4 C9 C10 127.64(12) C3 C4 C9 C10 -112.89(12) O3 C4 C9 C14 -176.28(11) C5 C4 C9 C14 -53.97(14) C3 C4 C9 C14 65.49(15) C14 C9 C10 C11 -3.11(19) C4 C9 C10 C11 175.31(11) C9 C10 C11 C12 0.2(2) C10 C11 C12 C13 3.2(2) C10 C11 C12 C15 -174.53(12) C11 C12 C13 C14 -3.50(19) C15 C12 C13 C14 174.14(12) C12 C13 C14 C9 0.53(19) C10 C9 C14 C13 2.74(18) C4 C9 C14 C13 -175.63(11) O2 C3 O1 C2 -4.2(2) C4 C3 O1 C2 174.28(11) C1 C2 O1 C3 -91.93(16) O5 C8 O4 C5 175.62(12) C7 C8 O4 C5 -3.98(14) C6 C5 O4 C8 4.33(13) C4 C5 O4 C8 126.41(10)