#------------------------------------------------------------------------------ #$Date: 2020-04-24 01:49:31 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251114 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240383.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_7240383 loop_ _publ_author_name 'Dai, Xia-Lin' 'Wu, Chao' 'Li, Jin-Hui' 'Liu, Lian-Chao' 'He, Xin' 'Lu, Tong-Bu' 'Chen, Jia-Mei' _publ_section_title ; Modulating the solubility and pharmacokinetic property of 5-fluorouracil via cocrystals ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00409J _journal_year 2020 _chemical_formula_moiety 'C4 H3 F N2 O2, C7 H6 O4' _chemical_formula_sum 'C11 H9 F N2 O6' _chemical_formula_weight 284.20 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2019-11-25 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-09 deposited with the CCDC. 2020-04-23 downloaded from the CCDC. ; _cell_angle_alpha 111.550(7) _cell_angle_beta 107.076(7) _cell_angle_gamma 100.662(6) _cell_formula_units_Z 2 _cell_length_a 7.8352(6) _cell_length_b 8.9191(7) _cell_length_c 9.4663(7) _cell_measurement_reflns_used 3598 _cell_measurement_temperature 150.01(10) _cell_measurement_theta_max 78.5570 _cell_measurement_theta_min 5.4680 _cell_volume 555.34(9) _computing_cell_refinement 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.01(10) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.960 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -28.00 68.00 0.50 0.50 -- 0.00 57.00-150.00 192 2 \w -29.00 41.00 0.50 0.50 -- 0.00 37.00 0.00 140 3 \w 51.00 85.00 0.50 0.50 -- 0.00 37.00 0.00 68 4 \w -27.00 10.00 0.50 0.50 -- 0.00 57.00 120.00 74 5 \w 75.00 113.00 0.50 0.50 -- 106.20 -82.00 150.00 76 6 \w 95.00 124.00 0.50 0.50 -- 106.20 61.00-150.00 58 7 \w 96.00 141.00 0.50 0.50 -- 106.20 45.00-180.00 90 8 \w 20.00 68.00 0.50 0.50 -- 106.20 -45.00-120.00 96 9 \w 106.00 132.00 0.50 0.50 -- 106.20 -77.00 -90.00 52 10 \w 33.00 73.00 0.50 0.50 -- 106.20 -82.00 -30.00 80 11 \w 82.00 148.00 0.50 0.50 -- 106.20 45.00-150.00 132 12 \w 80.00 179.00 0.50 0.50 -- 106.20 45.00 150.00 198 13 \w 38.00 137.00 0.50 0.50 -- 106.20 -82.00 60.00 198 14 \w 122.00 196.00 0.50 0.50 -- 106.20 45.00 60.00 148 15 \w 37.00 70.00 0.50 0.50 -- 106.20 -82.00-120.00 66 16 \w 17.00 91.00 0.50 0.50 -- 106.20 -77.00 -90.00 148 17 \w 86.00 162.00 0.50 0.50 -- 106.20 45.00 120.00 152 18 \w 78.00 132.00 0.50 0.50 -- 106.20 -82.00-120.00 108 19 \w 171.00 196.00 0.50 0.50 -- 106.20 61.00-150.00 50 20 \w 78.00 134.00 0.50 0.50 -- 106.20 -45.00-120.00 112 21 \w 150.00 192.00 0.50 0.50 -- 106.20 45.00-180.00 84 22 \w 90.00 130.00 0.50 0.50 -- 106.20 -82.00 -30.00 80 23 \w 96.00 141.00 0.50 0.50 -- 106.20 -77.00 30.00 90 24 \w 153.00 191.00 0.50 0.50 -- 106.20 45.00-150.00 76 25 \w 28.00 54.00 0.50 0.50 -- 106.20 -77.00 30.00 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0968933000 _diffrn_orient_matrix_UB_12 0.0298948000 _diffrn_orient_matrix_UB_13 0.1231715000 _diffrn_orient_matrix_UB_21 0.1941652000 _diffrn_orient_matrix_UB_22 0.0696631000 _diffrn_orient_matrix_UB_23 0.1443483000 _diffrn_orient_matrix_UB_31 0.0192005000 _diffrn_orient_matrix_UB_32 0.1814906000 _diffrn_orient_matrix_UB_33 0.0169744000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_unetI/netI 0.0659 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.960 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5446 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.960 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.650 _diffrn_reflns_theta_min 5.471 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.319 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.700 _exptl_crystal_description block _exptl_crystal_F_000 292 _refine_diff_density_max 0.529 _refine_diff_density_min -0.924 _refine_diff_density_rms 0.205 _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 184 _refine_ls_number_reflns 2323 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0900 _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^)+(0.1971P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2227 _refine_ls_wR_factor_ref 0.2295 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2062 _reflns_number_total 2323 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00409j2.cif _cod_data_source_block 5FU-35DHBA _cod_original_cell_volume 555.34(8) _cod_database_code 7240383 _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. ; _reflns_odcompleteness_completeness 99.16 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 74.33 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: N2(H2), N1(H1), C6(H6A), C8(H8), C10(H10), C4(H4A) 2.b Idealised tetrahedral OH refined as rotating group: O3(H3), O4(H4), O6(H6) ; _shelx_res_file ; TITL 5fu-35dhba_a.res in P-1 5fu-35dhba.res created by SHELXL-2016/6 at 10:07:54 on 25-Nov-2019 REM Old TITL 5fu-35dhba_a.res in P-1 REM SHELXT solution in P-1 REM R1 0.171, Rweak 0.003, Alpha 0.048, Orientation as input REM Formula found by SHELXT: C11 F N2 O6 CELL 1.54184 7.8352 8.9191 9.4663 111.55 107.076 100.662 ZERR 2 0.0006 0.0007 0.0007 0.007 0.007 0.006 LATT 1 SFAC C H F N O UNIT 22 18 2 4 12 EQIV $1 1-X,-Y,1-Z EQIV $2 -2+X,-1+Y,-1+Z EQIV $3 2-X,2-Y,2-Z L.S. 4 0 0 PLAN 20 HTAB O3 O5_$1 HTAB O4 O2_$2 HTAB O6 O1 HTAB N2 O5 HTAB N1 O1_$3 BOND $H conf list 4 fmap 2 53 acta REM REM REM WGHT 0.197100 FVAR 0.69428 F1 3 1.529192 0.682570 1.054935 11.00000 0.01155 0.02247 = 0.04647 0.01095 0.00518 0.01240 O1 5 0.861316 0.783821 0.891784 11.00000 0.00958 0.01236 = 0.03190 0.00724 0.00598 0.00738 O5 5 0.652900 0.358908 0.673333 11.00000 0.01010 0.01231 = 0.03485 0.00782 0.00498 0.00796 O3 5 0.093921 -0.190784 0.280272 11.00000 0.01462 0.00676 = 0.03371 0.00611 0.00576 0.00773 AFIX 147 H3 2 0.187445 -0.210041 0.326680 11.00000 -1.50000 AFIX 0 O4 5 -0.167174 0.260888 0.376661 11.00000 0.00866 0.01235 = 0.04151 0.00638 0.00395 0.00824 AFIX 147 H4 2 -0.265024 0.179950 0.315038 11.00000 -1.50000 AFIX 0 O6 5 0.516146 0.559573 0.690947 11.00000 0.01170 0.00848 = 0.03582 0.00420 0.00454 0.00625 AFIX 147 H6 2 0.621661 0.621563 0.761935 11.00000 -1.50000 AFIX 0 O2 5 1.499718 1.005092 1.165995 11.00000 0.01219 0.01626 = 0.03865 0.00345 0.00339 0.00275 N2 4 1.029637 0.600224 0.869797 11.00000 0.01147 0.00717 = 0.03021 0.00564 0.00610 0.00612 AFIX 43 H2 2 0.927903 0.513883 0.807327 11.00000 -1.20000 AFIX 0 N1 4 1.182217 0.891460 1.016906 11.00000 0.01048 0.00906 = 0.02826 0.00664 0.00626 0.00697 AFIX 43 H1 2 1.175854 0.992817 1.043789 11.00000 -1.20000 AFIX 0 C9 1 -0.018013 0.202967 0.398885 11.00000 0.00947 0.01441 = 0.02472 0.00850 0.00685 0.00931 C1 1 1.015157 0.758547 0.923866 11.00000 0.01259 0.00928 = 0.02400 0.00701 0.00702 0.00724 C6 1 0.299938 0.100310 0.454386 11.00000 0.01017 0.01119 = 0.02778 0.00836 0.00591 0.00896 AFIX 43 H6A 2 0.406215 0.066035 0.472238 11.00000 -1.20000 AFIX 0 C8 1 -0.038573 0.030795 0.324892 11.00000 0.01021 0.00989 = 0.02418 0.00679 0.00585 0.00445 AFIX 43 H8 2 -0.157624 -0.050308 0.256128 11.00000 -1.20000 AFIX 0 C5 1 0.318283 0.273521 0.527798 11.00000 0.01152 0.00797 = 0.02323 0.00634 0.00656 0.00705 C7 1 0.121941 -0.018900 0.355142 11.00000 0.01514 0.00783 = 0.02391 0.00723 0.00810 0.00850 C11 1 0.510579 0.399107 0.635747 11.00000 0.01135 0.01088 = 0.02327 0.00739 0.00599 0.00827 C10 1 0.160990 0.326547 0.500555 11.00000 0.01214 0.00997 = 0.02482 0.00641 0.00614 0.00790 AFIX 43 H10 2 0.174159 0.441850 0.548843 11.00000 -1.20000 AFIX 0 C2 1 1.360460 0.877760 1.071711 11.00000 0.01013 0.01609 = 0.02774 0.00937 0.00755 0.00778 C3 1 1.360251 0.705180 1.008665 11.00000 0.01019 0.01673 = 0.03112 0.01019 0.00613 0.01087 C4 1 1.199759 0.571257 0.910291 11.00000 0.01437 0.01161 = 0.03254 0.00816 0.00792 0.00979 AFIX 43 H4A 2 1.203974 0.460505 0.870234 11.00000 -1.20000 AFIX 0 HKLF 4 REM 5fu-35dhba_a.res in P-1 REM R1 = 0.0900 for 2062 Fo > 4sig(Fo) and 0.0930 for all 2323 data REM 184 parameters refined using 0 restraints END WGHT 0.1971 0.0000 REM Highest difference peak 0.529, deepest hole -0.924, 1-sigma level 0.205 Q1 1 -0.0473 0.1821 0.5477 11.00000 0.05 0.53 Q2 1 0.6967 0.7424 0.9410 11.00000 0.05 0.52 Q3 1 1.0759 0.9694 1.1289 11.00000 0.05 0.50 Q4 1 0.2458 -0.2767 0.4375 11.00000 0.05 0.49 Q5 1 0.4407 0.1961 0.4442 11.00000 0.05 0.47 Q6 1 0.5791 0.4039 0.8080 11.00000 0.05 0.47 Q7 1 1.6176 0.9022 1.1017 11.00000 0.05 0.45 Q8 1 0.2050 -0.2597 0.1744 11.00000 0.05 0.44 Q9 1 1.6844 0.6506 0.9672 11.00000 0.05 0.44 Q10 1 1.4325 0.6017 0.8809 11.00000 0.05 0.44 Q11 1 0.1880 -0.1125 0.2139 11.00000 0.05 0.43 Q12 1 0.7699 0.8271 1.0163 11.00000 0.05 0.43 Q13 1 0.1588 -0.0631 0.2032 11.00000 0.05 0.42 Q14 1 0.1112 -0.0184 0.5267 11.00000 0.05 0.42 Q15 1 0.6011 0.4212 0.5420 11.00000 0.05 0.41 Q16 1 1.4969 0.6752 1.2067 11.00000 0.05 0.41 Q17 1 0.3999 0.6799 0.7148 11.00000 0.05 0.41 Q18 1 1.4687 0.5560 1.1325 11.00000 0.05 0.40 Q19 1 1.2052 0.7627 1.1045 11.00000 0.05 0.40 Q20 1 -0.2390 0.3975 0.5170 11.00000 0.05 0.40 ; _shelx_res_checksum 67071 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.602 _oxdiff_exptl_absorpt_empirical_full_min 0.485 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 1.52919(16) 0.68257(15) 1.05494(16) 0.0288(4) Uani 1 1 d . . . . . O1 O 0.86132(19) 0.78382(16) 0.89178(17) 0.0188(4) Uani 1 1 d . . . . . O5 O 0.65290(18) 0.35891(16) 0.67333(18) 0.0203(4) Uani 1 1 d . . . . . O3 O 0.09392(17) -0.19078(15) 0.28027(17) 0.0196(4) Uani 1 1 d . . . . . H3 H 0.187445 -0.210041 0.326680 0.029 Uiso 1 1 calc GR . . . . O4 O -0.16717(19) 0.26089(16) 0.37666(19) 0.0235(4) Uani 1 1 d . . . . . H4 H -0.265024 0.179950 0.315038 0.035 Uiso 1 1 calc GR . . . . O6 O 0.51615(18) 0.55957(16) 0.69095(17) 0.0213(4) Uani 1 1 d . . . . . H6 H 0.621661 0.621563 0.761935 0.032 Uiso 1 1 calc GR . . . . O2 O 1.49972(19) 1.00509(17) 1.16599(18) 0.0273(4) Uani 1 1 d . . . . . N2 N 1.0296(2) 0.60022(19) 0.8698(2) 0.0172(4) Uani 1 1 d . . . . . H2 H 0.927903 0.513883 0.807327 0.021 Uiso 1 1 calc R . . . . N1 N 1.1822(2) 0.89146(18) 1.01691(19) 0.0163(4) Uani 1 1 d . . . . . H1 H 1.175854 0.992817 1.043789 0.020 Uiso 1 1 calc R . . . . C9 C -0.0180(2) 0.2030(2) 0.3989(2) 0.0154(4) Uani 1 1 d . . . . . C1 C 1.0152(3) 0.7585(2) 0.9239(2) 0.0149(4) Uani 1 1 d . . . . . C6 C 0.2999(2) 0.1003(2) 0.4544(2) 0.0161(4) Uani 1 1 d . . . . . H6A H 0.406215 0.066035 0.472238 0.019 Uiso 1 1 calc R . . . . C8 C -0.0386(2) 0.0308(2) 0.3249(2) 0.0151(4) Uani 1 1 d . . . . . H8 H -0.157624 -0.050308 0.256128 0.018 Uiso 1 1 calc R . . . . C5 C 0.3183(2) 0.27352(19) 0.5278(2) 0.0139(4) Uani 1 1 d . . . . . C7 C 0.1219(2) -0.0189(2) 0.3551(2) 0.0148(4) Uani 1 1 d . . . . . C11 C 0.5106(2) 0.3991(2) 0.6357(2) 0.0148(4) Uani 1 1 d . . . . . C10 C 0.1610(3) 0.3265(2) 0.5006(2) 0.0157(4) Uani 1 1 d . . . . . H10 H 0.174159 0.441850 0.548843 0.019 Uiso 1 1 calc R . . . . C2 C 1.3605(2) 0.8778(2) 1.0717(2) 0.0176(4) Uani 1 1 d . . . . . C3 C 1.3603(3) 0.7052(2) 1.0087(2) 0.0190(4) Uani 1 1 d . . . . . C4 C 1.1998(3) 0.5713(2) 0.9103(2) 0.0196(4) Uani 1 1 d . . . . . H4A H 1.203974 0.460505 0.870234 0.023 Uiso 1 1 calc R . . . . 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 0.0116(6) 0.0225(7) 0.0465(8) 0.0110(6) 0.0052(5) 0.0124(5) O1 0.0096(7) 0.0124(7) 0.0319(7) 0.0072(5) 0.0060(5) 0.0074(5) O5 0.0101(7) 0.0123(7) 0.0349(7) 0.0078(5) 0.0050(5) 0.0080(5) O3 0.0146(7) 0.0068(7) 0.0337(7) 0.0061(5) 0.0058(5) 0.0077(5) O4 0.0087(7) 0.0124(7) 0.0415(8) 0.0064(6) 0.0040(6) 0.0082(5) O6 0.0117(7) 0.0085(7) 0.0358(8) 0.0042(6) 0.0045(6) 0.0063(5) O2 0.0122(7) 0.0163(8) 0.0387(9) 0.0035(6) 0.0034(6) 0.0028(6) N2 0.0115(8) 0.0072(7) 0.0302(8) 0.0056(6) 0.0061(6) 0.0061(6) N1 0.0105(8) 0.0091(8) 0.0283(8) 0.0066(6) 0.0063(6) 0.0070(6) C9 0.0095(8) 0.0144(8) 0.0247(9) 0.0085(7) 0.0069(6) 0.0093(7) C1 0.0126(8) 0.0093(8) 0.0240(8) 0.0070(6) 0.0070(6) 0.0072(6) C6 0.0102(9) 0.0112(9) 0.0278(9) 0.0084(7) 0.0059(7) 0.0090(7) C8 0.0102(9) 0.0099(9) 0.0242(8) 0.0068(7) 0.0058(6) 0.0044(7) C5 0.0115(9) 0.0080(9) 0.0232(9) 0.0063(7) 0.0066(7) 0.0070(6) C7 0.0151(9) 0.0078(8) 0.0239(8) 0.0072(6) 0.0081(7) 0.0085(7) C11 0.0113(8) 0.0109(8) 0.0233(8) 0.0074(6) 0.0060(6) 0.0083(6) C10 0.0121(9) 0.0100(8) 0.0248(9) 0.0064(7) 0.0061(7) 0.0079(7) C2 0.0101(9) 0.0161(9) 0.0277(9) 0.0094(7) 0.0076(7) 0.0078(7) C3 0.0102(9) 0.0167(9) 0.0311(9) 0.0102(7) 0.0061(7) 0.0109(7) C4 0.0144(9) 0.0116(8) 0.0325(10) 0.0082(7) 0.0079(7) 0.0098(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C7 O3 H3 109.5 . . ? C9 O4 H4 109.5 . . ? C11 O6 H6 109.5 . . ? C1 N2 H2 118.5 . . ? C1 N2 C4 122.92(16) . . ? C4 N2 H2 118.5 . . ? C1 N1 H1 117.0 . . ? C1 N1 C2 126.05(15) . . ? C2 N1 H1 117.0 . . ? O4 C9 C8 122.50(16) . . ? O4 C9 C10 116.54(15) . . ? C8 C9 C10 120.96(16) . . ? O1 C1 N2 122.73(16) . . ? O1 C1 N1 121.29(16) . . ? N2 C1 N1 115.98(15) . . ? C5 C6 H6A 120.4 . . ? C7 C6 H6A 120.4 . . ? C7 C6 C5 119.10(15) . . ? C9 C8 H8 120.5 . . ? C9 C8 C7 119.07(17) . . ? C7 C8 H8 120.5 . . ? C6 C5 C11 118.17(14) . . ? C10 C5 C6 121.02(16) . . ? C10 C5 C11 120.81(14) . . ? O3 C7 C6 122.06(14) . . ? O3 C7 C8 116.83(16) . . ? C6 C7 C8 121.11(16) . . ? O5 C11 O6 122.31(16) . . ? O5 C11 C5 123.58(14) . . ? O6 C11 C5 114.10(13) . . ? C9 C10 H10 120.6 . . ? C5 C10 C9 118.72(15) . . ? C5 C10 H10 120.6 . . ? O2 C2 N1 120.86(16) . . ? O2 C2 C3 125.80(16) . . ? N1 C2 C3 113.33(16) . . ? F1 C3 C2 116.52(16) . . ? F1 C3 C4 121.23(17) . . ? C4 C3 C2 122.24(16) . . ? N2 C4 H4A 120.4 . . ? C3 C4 N2 119.22(17) . . ? C3 C4 H4A 120.4 . . ? 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 1.345(2) . ? O1 C1 1.238(2) . ? O5 C11 1.228(2) . ? O3 H3 0.8200 . ? O3 C7 1.3735(19) . ? O4 H4 0.8200 . ? O4 C9 1.3549(19) . ? O6 H6 0.8200 . ? O6 C11 1.318(2) . ? O2 C2 1.225(2) . ? N2 H2 0.8600 . ? N2 C1 1.353(2) . ? N2 C4 1.375(2) . ? N1 H1 0.8600 . ? N1 C1 1.370(2) . ? N1 C2 1.385(2) . ? C9 C8 1.388(2) . ? C9 C10 1.401(2) . ? C6 H6A 0.9300 . ? C6 C5 1.400(2) . ? C6 C7 1.381(2) . ? C8 H8 0.9300 . ? C8 C7 1.396(2) . ? C5 C11 1.483(2) . ? C5 C10 1.388(2) . ? C10 H10 0.9300 . ? C2 C3 1.431(3) . ? C3 C4 1.347(3) . ? C4 H4A 0.9300 . ? 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 O3 H3 O5 0.82 1.99 2.7294(18) 150.5 2_656 O4 H4 O2 0.82 1.90 2.7187(19) 175.1 1_344 O6 H6 O1 0.82 1.86 2.6673(19) 167.4 . N2 H2 O5 0.86 2.04 2.879(2) 164.4 . N1 H1 O1 0.86 1.96 2.820(2) 174.4 2_777 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 F1 C3 C4 N2 178.23(15) . . . . ? O4 C9 C8 C7 -179.40(15) . . . . ? O4 C9 C10 C5 179.70(15) . . . . ? O2 C2 C3 F1 -1.6(3) . . . . ? O2 C2 C3 C4 177.4(2) . . . . ? N1 C2 C3 F1 179.03(15) . . . . ? N1 C2 C3 C4 -2.1(3) . . . . ? C9 C8 C7 O3 179.42(14) . . . . ? C9 C8 C7 C6 -1.3(3) . . . . ? C1 N2 C4 C3 0.3(3) . . . . ? C1 N1 C2 O2 -173.84(17) . . . . ? C1 N1 C2 C3 5.6(3) . . . . ? C6 C5 C11 O5 -5.2(3) . . . . ? C6 C5 C11 O6 175.82(15) . . . . ? C6 C5 C10 C9 0.6(3) . . . . ? C8 C9 C10 C5 -0.7(3) . . . . ? C5 C6 C7 O3 -179.60(15) . . . . ? C5 C6 C7 C8 1.1(3) . . . . ? C7 C6 C5 C11 179.18(14) . . . . ? C7 C6 C5 C10 -0.8(3) . . . . ? C11 C5 C10 C9 -179.37(15) . . . . ? C10 C9 C8 C7 1.1(3) . . . . ? C10 C5 C11 O5 174.78(16) . . . . ? C10 C5 C11 O6 -4.2(2) . . . . ? C2 N1 C1 O1 174.19(17) . . . . ? C2 N1 C1 N2 -6.0(3) . . . . ? C2 C3 C4 N2 -0.6(3) . . . . ? C4 N2 C1 O1 -177.47(16) . . . . ? C4 N2 C1 N1 2.8(3) . . . . ?