#------------------------------------------------------------------------------ #$Date: 2021-04-27 03:06:30 +0300 (Tue, 27 Apr 2021) $ #$Revision: 264559 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/21/1562114.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_1562114 loop_ _publ_author_name 'Yu, Yue-Ming' 'Niu, Yuan-Yuan' 'Wang, Ling-Yang' 'Li, Yan-Tuan' 'Wu, Zhi-Yong' 'Yan, Cui-Wei' _publ_section_title ; Supramolecular self-assembly and perfected in vitro/vivo property of 5-fluorouracil and ferulic acid on the strength of double optimized strategy: the first 5-fluorouracial-phenolic acid nutraceutical cocrystal with synergistic antitumor efficacy ; _journal_issue 8 _journal_name_full 'The Analyst' _journal_page_first 2506 _journal_page_last 2519 _journal_paper_doi 10.1039/D1AN00171J _journal_volume 146 _journal_year 2021 _chemical_formula_moiety 'C4 H3 F N2 O2, C10 H10 O4, H2 O' _chemical_formula_sum 'C14 H15 F N2 O7' _chemical_formula_weight 342.28 _chemical_melting_point 502.45 _chemical_name_common '5-Fluorouracil Ferulic Acid Hydrate' _chemical_name_systematic '5-Fluoropyrimidine-2,4(1H,3H)-dione 3-(4-Hydroxy-3-methoxyphenyl)acrylic acid Hydrate' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2016/4 _audit_update_record ; 2020-09-25 deposited with the CCDC. 2021-03-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.502(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6479(4) _cell_length_b 6.3464(3) _cell_length_c 30.7977(16) _cell_measurement_reflns_used 7723 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.63 _cell_measurement_theta_min 3.28 _cell_volume 1490.20(13) _computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type bruker _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_unetI/netI 0.0327 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 22470 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 3.204 _exptl_absorpt_coefficient_mu 0.131 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.526 _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Ethanol/water/acetonitrile' _exptl_crystal_size_max 0.425 _exptl_crystal_size_mid 0.176 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.185 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 3411 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0451 _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^)+(0.0532P)^2^+0.3601P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0994 _refine_ls_wR_factor_ref 0.1123 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2360 _reflns_number_total 3411 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1an00171j2.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1562114 _shelx_shelxl_version_number 2016/4 _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 0.946 _shelx_estimated_absorpt_t_max 0.990 _shelx_res_file ; TITL SIR2004 run in space group P 21/n shelx.res created by SHELXL-2016/4 at 10:11:50 on 01-Oct-2018 CELL 0.71073 7.6479 6.3464 30.7977 90.000 94.502 90.000 ZERR 4.00 0.0004 0.0003 0.0016 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O F UNIT 56 60 8 28 4 MERG 2 FMAP 2 PLAN 15 SIZE 0.080 0.176 0.425 ACTA BOND $H CONF L.S. 10 TEMP 23.00 WGHT 0.053200 0.360100 FVAR 0.22482 F1 5 0.424351 0.813019 0.141048 11.00000 0.06595 0.04111 = 0.05803 -0.00594 0.01075 0.01578 O1 4 0.706756 0.069165 0.107170 11.00000 0.06919 0.03815 = 0.03453 -0.00031 0.00794 0.01462 O2 4 0.540286 0.542055 0.206232 11.00000 0.05874 0.06020 = 0.02960 -0.00776 0.00929 0.00886 N1 3 0.617450 0.304299 0.156024 11.00000 0.04261 0.03702 = 0.02716 0.00236 0.00459 0.00382 N2 3 0.592950 0.381251 0.082746 11.00000 0.04724 0.03624 = 0.02396 -0.00171 0.00472 0.00258 C1 1 0.642777 0.242253 0.114415 11.00000 0.03657 0.03200 = 0.02959 -0.00084 0.00422 -0.00195 C2 1 0.519198 0.573044 0.090800 11.00000 0.04304 0.03396 = 0.03449 0.00410 0.00180 0.00285 C3 1 0.498420 0.628483 0.131651 11.00000 0.03664 0.03007 = 0.04109 -0.00391 0.00535 0.00339 C4 1 0.551221 0.495647 0.168025 11.00000 0.03261 0.03939 = 0.03242 -0.00437 0.00624 -0.00127 O3 4 0.174160 0.288415 0.500934 11.00000 0.09162 0.04733 = 0.03394 -0.00176 0.00922 -0.02407 O4 4 0.262429 0.590587 0.531781 11.00000 0.08326 0.04525 = 0.02866 -0.00079 0.00605 -0.01691 O5 4 0.405859 0.774782 0.294070 11.00000 0.06435 0.04468 = 0.03089 -0.00650 0.01061 -0.01774 O6 4 0.556244 1.150927 0.304117 11.00000 0.06268 0.04002 = 0.04004 0.00256 0.01349 -0.01227 C5 1 0.232328 0.465799 0.497873 11.00000 0.04457 0.04243 = 0.03058 0.00170 0.00405 -0.00371 C6 1 0.273996 0.557157 0.456402 11.00000 0.05217 0.04215 = 0.03089 -0.00189 0.00495 -0.00481 C7 1 0.338042 0.748007 0.452259 11.00000 0.04268 0.04438 = 0.02844 -0.00178 0.00084 -0.00126 C8 1 0.388292 0.850068 0.412626 11.00000 0.03432 0.03551 = 0.03114 0.00124 0.00149 -0.00053 C9 1 0.365313 0.753464 0.371681 11.00000 0.03796 0.03021 = 0.03331 0.00157 0.00351 -0.00531 C10 1 0.418681 0.852568 0.335415 11.00000 0.03447 0.03321 = 0.03033 -0.00270 0.00217 -0.00022 C11 1 0.497930 1.052251 0.339248 11.00000 0.03325 0.03358 = 0.03441 0.00387 0.00413 -0.00105 C12 1 0.517471 1.149928 0.379132 11.00000 0.04282 0.02934 = 0.04357 -0.00182 -0.00048 -0.00721 C13 1 0.463106 1.049167 0.415463 11.00000 0.04375 0.03971 = 0.03170 -0.00482 -0.00182 -0.00389 C14 1 0.297933 0.595711 0.285381 11.00000 0.05817 0.04484 = 0.04187 -0.01480 0.01165 -0.01363 O7 4 0.670488 0.992223 0.225308 11.00000 0.07134 0.04728 = 0.04236 -0.00357 -0.00375 0.01159 H1 2 0.648993 0.208905 0.175966 11.00000 0.05609 H2 2 0.481370 0.661510 0.067237 11.00000 0.04536 H2A 2 0.608999 0.348959 0.055835 11.00000 0.05124 H4 2 0.235286 0.527173 0.555892 11.00000 0.07767 H6 2 0.258256 0.462312 0.432515 11.00000 0.05224 H6A 2 0.555850 1.070908 0.284338 11.00000 0.07065 H7 2 0.354084 0.825731 0.477307 11.00000 0.05216 H7A 2 0.641753 0.870355 0.217916 11.00000 0.10149 H7B 2 0.779604 0.997944 0.232123 11.00000 0.10174 H9 2 0.318050 0.615890 0.369465 11.00000 0.03275 H12 2 0.567193 1.280679 0.380352 11.00000 0.03584 H13 2 0.480116 1.112938 0.442509 11.00000 0.03926 H14A 2 0.301612 0.566686 0.254296 11.00000 0.05807 H14B 2 0.351236 0.472549 0.301049 11.00000 0.06682 H14C 2 0.180989 0.621381 0.295251 11.00000 0.06446 HKLF 4 REM SIR2004 run in space group P 21/n REM R1 = 0.0451 for 2360 Fo > 4sig(Fo) and 0.0784 for all 3411 data REM 277 parameters refined using 0 restraints END WGHT 0.0532 0.3599 REM Highest difference peak 0.185, deepest hole -0.287, 1-sigma level 0.051 Q1 1 0.3440 0.8448 0.3494 11.00000 0.05 0.19 Q2 1 0.4180 0.7617 0.3976 11.00000 0.05 0.18 Q3 1 0.5790 0.4344 0.0252 11.00000 0.05 0.18 Q4 1 0.3753 0.7746 0.4295 11.00000 0.05 0.17 Q5 1 0.4270 0.4815 0.3674 11.00000 0.05 0.15 Q6 1 0.4572 0.8142 0.2709 11.00000 0.05 0.14 Q7 1 0.4449 0.5683 0.1096 11.00000 0.05 0.14 Q8 1 0.4459 0.7707 0.3531 11.00000 0.05 0.14 Q9 1 0.9559 1.1622 0.2420 11.00000 0.05 0.14 Q10 1 0.7771 1.0357 0.2101 11.00000 0.05 0.13 Q11 1 0.5979 0.1009 0.0927 11.00000 0.05 0.13 Q12 1 0.7363 1.1491 0.3908 11.00000 0.05 0.13 Q13 1 0.3337 0.8448 0.3977 11.00000 0.05 0.13 Q14 1 0.7010 0.4912 0.0318 11.00000 0.05 0.13 Q15 1 0.5384 -0.0134 0.1202 11.00000 0.05 0.13 ; _shelx_res_checksum 99364 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 F1 F 0.42435(15) 0.81302(17) 0.14105(4) 0.0547(3) Uani 1 1 d . . . . . O1 O 0.70676(18) 0.06917(19) 0.10717(4) 0.0471(3) Uani 1 1 d . . . . . O2 O 0.54029(17) 0.5421(2) 0.20623(4) 0.0492(4) Uani 1 1 d . . . . . N1 N 0.61745(18) 0.3043(2) 0.15602(4) 0.0355(3) Uani 1 1 d . . . . . N2 N 0.59295(19) 0.3813(2) 0.08275(5) 0.0357(3) Uani 1 1 d . . . . . C1 C 0.6428(2) 0.2423(3) 0.11442(5) 0.0326(4) Uani 1 1 d . . . . . C2 C 0.5192(2) 0.5730(3) 0.09080(6) 0.0372(4) Uani 1 1 d . . . . . C3 C 0.4984(2) 0.6285(3) 0.13165(6) 0.0358(4) Uani 1 1 d . . . . . C4 C 0.5512(2) 0.4956(3) 0.16802(5) 0.0346(4) Uani 1 1 d . . . . . O3 O 0.1742(2) 0.2884(2) 0.50093(4) 0.0574(4) Uani 1 1 d . . . . . O4 O 0.2624(2) 0.5906(2) 0.53178(4) 0.0523(4) Uani 1 1 d . . . . . O5 O 0.40586(17) 0.7748(2) 0.29407(4) 0.0463(3) Uani 1 1 d . . . . . O6 O 0.55624(18) 1.1509(2) 0.30412(5) 0.0471(3) Uani 1 1 d . . . . . C5 C 0.2323(2) 0.4658(3) 0.49787(5) 0.0391(4) Uani 1 1 d . . . . . C6 C 0.2740(3) 0.5572(3) 0.45640(6) 0.0416(4) Uani 1 1 d . . . . . C7 C 0.3380(2) 0.7480(3) 0.45226(6) 0.0386(4) Uani 1 1 d . . . . . C8 C 0.3883(2) 0.8501(3) 0.41263(5) 0.0337(4) Uani 1 1 d . . . . . C9 C 0.3653(2) 0.7535(3) 0.37168(5) 0.0338(4) Uani 1 1 d . . . . . C10 C 0.4187(2) 0.8526(3) 0.33542(5) 0.0327(4) Uani 1 1 d . . . . . C11 C 0.4979(2) 1.0523(3) 0.33925(5) 0.0337(4) Uani 1 1 d . . . . . C12 C 0.5175(2) 1.1499(3) 0.37913(6) 0.0388(4) Uani 1 1 d . . . . . C13 C 0.4631(2) 1.0492(3) 0.41546(6) 0.0386(4) Uani 1 1 d . . . . . C14 C 0.2979(3) 0.5957(3) 0.28538(7) 0.0479(5) Uani 1 1 d . . . . . O7 O 0.6705(3) 0.9922(3) 0.22531(5) 0.0541(4) Uani 1 1 d . . . . . H1 H 0.649(3) 0.209(3) 0.1760(7) 0.056(6) Uiso 1 1 d . . . . . H2 H 0.481(2) 0.662(3) 0.0672(6) 0.045(5) Uiso 1 1 d . . . . . H2A H 0.609(2) 0.349(3) 0.0558(7) 0.051(6) Uiso 1 1 d . . . . . H4 H 0.235(3) 0.527(4) 0.5559(9) 0.078(8) Uiso 1 1 d . . . . . H6 H 0.258(2) 0.462(3) 0.4325(7) 0.052(6) Uiso 1 1 d . . . . . H6A H 0.556(3) 1.071(4) 0.2843(8) 0.071(8) Uiso 1 1 d . . . . . H7 H 0.354(2) 0.826(3) 0.4773(7) 0.052(6) Uiso 1 1 d . . . . . H7A H 0.642(4) 0.870(5) 0.2179(10) 0.101(11) Uiso 1 1 d . . . . . H7B H 0.780(4) 0.998(5) 0.2321(10) 0.102(11) Uiso 1 1 d . . . . . H9 H 0.318(2) 0.616(3) 0.3695(5) 0.033(4) Uiso 1 1 d . . . . . H12 H 0.567(2) 1.281(3) 0.3804(6) 0.036(5) Uiso 1 1 d . . . . . H13 H 0.480(2) 1.113(3) 0.4425(6) 0.039(5) Uiso 1 1 d . . . . . H14A H 0.302(3) 0.567(3) 0.2543(7) 0.058(6) Uiso 1 1 d . . . . . H14B H 0.351(3) 0.473(4) 0.3010(7) 0.067(7) Uiso 1 1 d . . . . . H14C H 0.181(3) 0.621(3) 0.2953(7) 0.064(6) Uiso 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 F1 0.0660(7) 0.0411(6) 0.0580(7) -0.0059(5) 0.0107(6) 0.0158(5) O1 0.0692(9) 0.0382(7) 0.0345(7) -0.0003(5) 0.0079(6) 0.0146(6) O2 0.0587(8) 0.0602(9) 0.0296(6) -0.0078(6) 0.0093(6) 0.0089(7) N1 0.0426(8) 0.0370(8) 0.0272(7) 0.0024(6) 0.0046(6) 0.0038(7) N2 0.0472(8) 0.0362(8) 0.0240(7) -0.0017(6) 0.0047(6) 0.0026(7) C1 0.0366(8) 0.0320(9) 0.0296(8) -0.0008(7) 0.0042(7) -0.0019(7) C2 0.0430(9) 0.0340(9) 0.0345(9) 0.0041(8) 0.0018(7) 0.0028(8) C3 0.0366(9) 0.0301(9) 0.0411(10) -0.0039(7) 0.0053(7) 0.0034(7) C4 0.0326(8) 0.0394(9) 0.0324(9) -0.0044(7) 0.0062(7) -0.0013(8) O3 0.0916(11) 0.0473(8) 0.0339(7) -0.0018(6) 0.0092(7) -0.0241(8) O4 0.0833(10) 0.0452(8) 0.0287(7) -0.0008(6) 0.0060(6) -0.0169(7) O5 0.0644(8) 0.0447(7) 0.0309(6) -0.0065(5) 0.0106(6) -0.0177(6) O6 0.0627(9) 0.0400(8) 0.0400(7) 0.0026(6) 0.0135(6) -0.0123(6) C5 0.0446(10) 0.0424(11) 0.0306(9) 0.0017(8) 0.0041(7) -0.0037(8) C6 0.0522(11) 0.0421(11) 0.0309(9) -0.0019(8) 0.0049(8) -0.0048(9) C7 0.0427(10) 0.0444(11) 0.0284(9) -0.0018(8) 0.0008(7) -0.0013(8) C8 0.0343(8) 0.0355(9) 0.0311(8) 0.0012(7) 0.0015(7) -0.0005(7) C9 0.0380(9) 0.0302(9) 0.0333(9) 0.0016(7) 0.0035(7) -0.0053(8) C10 0.0345(8) 0.0332(9) 0.0303(8) -0.0027(7) 0.0022(7) -0.0002(7) C11 0.0332(9) 0.0336(9) 0.0344(8) 0.0039(7) 0.0041(7) -0.0010(7) C12 0.0428(10) 0.0293(9) 0.0436(10) -0.0018(8) -0.0005(8) -0.0072(8) C13 0.0437(10) 0.0397(10) 0.0317(9) -0.0048(8) -0.0018(7) -0.0039(8) C14 0.0582(13) 0.0448(12) 0.0419(11) -0.0148(9) 0.0116(10) -0.0136(10) O7 0.0713(11) 0.0473(9) 0.0424(8) -0.0036(7) -0.0037(7) 0.0116(8) 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' F F 0.0171 0.0103 '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 C1 N1 C4 125.94(15) . . ? C1 N1 H1 113.8(14) . . ? C4 N1 H1 120.3(14) . . ? C1 N2 C2 123.14(15) . . ? C1 N2 H2A 118.8(13) . . ? C2 N2 H2A 118.1(13) . . ? O1 C1 N2 123.17(15) . . ? O1 C1 N1 120.95(15) . . ? N2 C1 N1 115.88(15) . . ? C3 C2 N2 119.19(16) . . ? C3 C2 H2 121.2(11) . . ? N2 C2 H2 119.6(11) . . ? C2 C3 F1 121.29(16) . . ? C2 C3 C4 122.47(16) . . ? F1 C3 C4 116.24(14) . . ? O2 C4 N1 121.68(16) . . ? O2 C4 C3 125.02(16) . . ? N1 C4 C3 113.30(14) . . ? C5 O4 H4 110.8(16) . . ? C10 O5 C14 117.72(14) . . ? C11 O6 H6A 109.6(18) . . ? O3 C5 O4 122.50(15) . . ? O3 C5 C6 122.77(16) . . ? O4 C5 C6 114.73(16) . . ? C7 C6 C5 123.95(17) . . ? C7 C6 H6 122.2(12) . . ? C5 C6 H6 113.7(12) . . ? C6 C7 C8 127.86(17) . . ? C6 C7 H7 116.1(13) . . ? C8 C7 H7 116.0(13) . . ? C13 C8 C9 118.52(15) . . ? C13 C8 C7 119.08(15) . . ? C9 C8 C7 122.40(16) . . ? C10 C9 C8 120.53(16) . . ? C10 C9 H9 120.1(10) . . ? C8 C9 H9 119.3(10) . . ? O5 C10 C9 126.22(15) . . ? O5 C10 C11 113.84(14) . . ? C9 C10 C11 119.93(15) . . ? O6 C11 C12 119.06(15) . . ? O6 C11 C10 121.08(15) . . ? C12 C11 C10 119.86(15) . . ? C11 C12 C13 119.81(16) . . ? C11 C12 H12 117.6(11) . . ? C13 C12 H12 122.6(11) . . ? C12 C13 C8 121.32(16) . . ? C12 C13 H13 119.8(11) . . ? C8 C13 H13 118.9(11) . . ? O5 C14 H14A 106.0(12) . . ? O5 C14 H14B 109.3(13) . . ? H14A C14 H14B 106.6(18) . . ? O5 C14 H14C 109.9(13) . . ? H14A C14 H14C 115.6(17) . . ? H14B C14 H14C 109.3(18) . . ? H7A O7 H7B 110(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 F1 C3 1.3424(19) . ? O1 C1 1.2300(19) . ? O2 C4 1.2222(19) . ? N1 C1 1.369(2) . ? N1 C4 1.377(2) . ? N1 H1 0.88(2) . ? N2 C1 1.348(2) . ? N2 C2 1.372(2) . ? N2 H2A 0.87(2) . ? C2 C3 1.328(2) . ? C2 H2 0.94(2) . ? C3 C4 1.434(2) . ? O3 C5 1.217(2) . ? O4 C5 1.316(2) . ? O4 H4 0.88(3) . ? O5 C10 1.3620(19) . ? O5 C14 1.418(2) . ? O6 C11 1.356(2) . ? O6 H6A 0.79(2) . ? C5 C6 1.460(2) . ? C6 C7 1.316(3) . ? C6 H6 0.95(2) . ? C7 C8 1.460(2) . ? C7 H7 0.92(2) . ? C8 C13 1.387(2) . ? C8 C9 1.401(2) . ? C9 C10 1.372(2) . ? C9 H9 0.945(18) . ? C10 C11 1.406(2) . ? C11 C12 1.374(2) . ? C12 C13 1.381(3) . ? C12 H12 0.912(18) . ? C13 H13 0.926(19) . ? C14 H14A 0.98(2) . ? C14 H14B 0.99(2) . ? C14 H14C 0.98(2) . ? O7 H7A 0.83(3) . ? O7 H7B 0.85(3) . ? 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 C2 N2 C1 O1 179.01(16) . . . . ? C2 N2 C1 N1 -0.7(2) . . . . ? C4 N1 C1 O1 178.30(15) . . . . ? C4 N1 C1 N2 -1.9(2) . . . . ? C1 N2 C2 C3 1.5(3) . . . . ? N2 C2 C3 F1 -178.92(15) . . . . ? N2 C2 C3 C4 0.4(3) . . . . ? C1 N1 C4 O2 -176.61(16) . . . . ? C1 N1 C4 C3 3.5(2) . . . . ? C2 C3 C4 O2 177.48(17) . . . . ? F1 C3 C4 O2 -3.2(3) . . . . ? C2 C3 C4 N1 -2.6(2) . . . . ? F1 C3 C4 N1 176.70(14) . . . . ? O3 C5 C6 C7 -179.55(19) . . . . ? O4 C5 C6 C7 0.5(3) . . . . ? C5 C6 C7 C8 178.05(17) . . . . ? C6 C7 C8 C13 -176.33(19) . . . . ? C6 C7 C8 C9 3.0(3) . . . . ? C13 C8 C9 C10 1.1(3) . . . . ? C7 C8 C9 C10 -178.23(15) . . . . ? C14 O5 C10 C9 13.4(3) . . . . ? C14 O5 C10 C11 -167.78(16) . . . . ? C8 C9 C10 O5 179.11(16) . . . . ? C8 C9 C10 C11 0.3(2) . . . . ? O5 C10 C11 O6 -0.8(2) . . . . ? C9 C10 C11 O6 178.14(15) . . . . ? O5 C10 C11 C12 179.35(15) . . . . ? C9 C10 C11 C12 -1.7(2) . . . . ? O6 C11 C12 C13 -178.25(16) . . . . ? C10 C11 C12 C13 1.6(3) . . . . ? C11 C12 C13 C8 -0.1(3) . . . . ? C9 C8 C13 C12 -1.3(3) . . . . ? C7 C8 C13 C12 178.14(16) . . . . ?