#------------------------------------------------------------------------------ #$Date: 2020-04-24 01:49:31 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251114 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240385.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_7240385 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 'C7 H6 O4, C4 H3 F N2 O2' _chemical_formula_sum 'C11 H9 F N2 O6' _chemical_formula_weight 284.20 _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 geom _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 90 _cell_angle_beta 94.115(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5121(4) _cell_length_b 5.5084(3) _cell_length_c 21.2993(8) _cell_measurement_reflns_used 2350 _cell_measurement_temperature 150(10) _cell_measurement_theta_max 67.0340 _cell_measurement_theta_min 4.1200 _cell_volume 1113.13(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _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 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_environment air _diffrn_ambient_temperature 150(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5058 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -22.00 75.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 38.3352 -99.0000 90.0000 97 #__ type_ start__ end____ width___ exp.time_ 2 omega 37.00 88.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -112.0000 90.0000 51 #__ type_ start__ end____ width___ exp.time_ 3 omega 50.00 75.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -45.0000 120.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega 10.00 82.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -95.0000 0.0000 72 #__ type_ start__ end____ width___ exp.time_ 5 omega 40.00 67.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 38.3352 -99.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega 25.00 75.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -112.0000 -120.0000 50 #__ type_ start__ end____ width___ exp.time_ 7 omega 52.00 78.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -95.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 17.00 50.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -112.0000 -150.0000 33 #__ type_ start__ end____ width___ exp.time_ 9 omega -24.00 37.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 38.3352 -99.0000 -120.0000 61 #__ type_ start__ end____ width___ exp.time_ 10 omega 78.00 104.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 45.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 11 omega 118.00 158.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 45.0000 -180.0000 40 #__ type_ start__ end____ width___ exp.time_ 12 omega 133.00 159.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 61.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 13 omega 79.00 168.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 112.0000 -120.0000 89 #__ type_ start__ end____ width___ exp.time_ 14 omega 79.00 158.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 112.0000 0.0000 79 #__ type_ start__ end____ width___ exp.time_ 15 omega 83.00 114.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 38.3352 126.0000 90.0000 31 #__ type_ start__ end____ width___ exp.time_ 16 omega 135.00 169.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 77.0000 150.0000 34 #__ type_ start__ end____ width___ exp.time_ 17 omega 63.00 88.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 77.0000 150.0000 25 #__ type_ start__ end____ width___ exp.time_ 18 omega 10.00 39.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 -95.0000 150.0000 29 #__ type_ start__ end____ width___ exp.time_ 19 omega 76.00 126.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - 96.5000 61.0000 -120.0000 50 #__ type_ start__ end____ width___ exp.time_ 20 omega -86.00 -58.00 1.0000 3.5000 omega____ theta____ kappa____ phi______ frames - -90.0000 54.0000 105.0000 28 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0259273000 _diffrn_orient_matrix_UB_12 -0.2338459000 _diffrn_orient_matrix_UB_13 -0.0387858000 _diffrn_orient_matrix_UB_21 0.1457027000 _diffrn_orient_matrix_UB_22 0.0277595000 _diffrn_orient_matrix_UB_23 -0.0264158000 _diffrn_orient_matrix_UB_31 0.0667505000 _diffrn_orient_matrix_UB_32 -0.1509405000 _diffrn_orient_matrix_UB_33 0.0552909000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_unetI/netI 0.0254 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 5282 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.265 _diffrn_reflns_theta_max 67.265 _diffrn_reflns_theta_min 4.162 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.316 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74859 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 584 _refine_diff_density_max 0.216 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 184 _refine_ls_number_reflns 1995 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.131 _refine_ls_R_factor_all 0.0469 _refine_ls_R_factor_gt 0.0393 _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^)+(0.0601P)^2^+0.2862P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1060 _refine_ls_wR_factor_ref 0.1121 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1712 _reflns_number_total 1995 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00409j2.cif _cod_data_source_block 5FU-25DHBA _cod_database_code 7240385 _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 99.55 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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: C4(H4), C5(H5), C7(H7), C9(H9), N1(H1), N2(H2A) 2.b Idealised tetrahedral OH refined as rotating group: O2(H2), O3(H3), O4(H4A) ; _shelx_res_file ; TITL exp_10835 in P2(1)/n exp_10835.res created by SHELXL-2016/6 at 11:52:52 on 25-Nov-2019 CELL 1.54178 9.5121 5.5084 21.2993 90 94.115 90 ZERR 4 0.0004 0.0003 0.0008 0 0.004 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N O UNIT 44 36 4 8 24 EQIV $1 1-X,-Y,-Z EQIV $2 +X,-1+Y,+Z EQIV $3 +X,1+Y,+Z EQIV $4 1+X,-1+Y,+Z L.S. 4 PLAN 5 HTAB N1 O4_$1 HTAB N2 O1_$2 HTAB O2 O5_$3 HTAB O3 O1 HTAB O4 O6_$4 BOND $H CONF fmap 2 acta REM REM REM WGHT 0.060100 0.286200 FVAR 5.09363 C1 1 0.664256 0.589112 0.117242 11.00000 0.02025 0.02258 = 0.02026 0.00137 -0.00237 -0.00020 C2 1 0.775562 0.404568 0.128113 11.00000 0.01873 0.01969 = 0.02130 0.00262 -0.00155 0.00114 C3 1 0.864875 0.414233 0.183802 11.00000 0.02182 0.02118 = 0.02017 0.00086 -0.00104 -0.00091 C4 1 0.969754 0.238930 0.193076 11.00000 0.02155 0.02760 = 0.02061 0.00423 -0.00536 0.00074 AFIX 43 H4 2 1.030742 0.244786 0.229179 11.00000 -1.20000 AFIX 0 C5 1 0.984749 0.056924 0.149690 11.00000 0.02037 0.02279 = 0.02698 0.00681 -0.00264 0.00328 AFIX 43 H5 2 1.054664 -0.059820 0.156935 11.00000 -1.20000 AFIX 0 C6 1 0.895182 0.047436 0.094874 11.00000 0.02152 0.02077 = 0.02391 0.00001 -0.00094 0.00225 C7 1 0.792457 0.221814 0.083989 11.00000 0.02113 0.02327 = 0.02136 0.00140 -0.00421 0.00155 AFIX 43 H7 2 0.734129 0.217592 0.047045 11.00000 -1.20000 AFIX 0 C8 1 0.366988 0.073618 0.082413 11.00000 0.02089 0.02424 = 0.02397 0.00095 -0.00251 0.00357 C9 1 0.398178 0.303059 0.178073 11.00000 0.02242 0.02628 = 0.02333 -0.00187 -0.00521 0.00084 AFIX 43 H9 2 0.444906 0.322943 0.217607 11.00000 -1.20000 AFIX 0 C10 1 0.296343 0.457535 0.158311 11.00000 0.02399 0.02270 = 0.02706 -0.00594 -0.00191 0.00200 C11 1 0.220169 0.433457 0.097192 11.00000 0.01947 0.02214 = 0.02606 0.00162 -0.00131 0.00271 F1 3 0.258724 0.643482 0.194481 11.00000 0.03741 0.03434 = 0.03893 -0.01705 -0.01078 0.01301 N1 4 0.262307 0.235140 0.064072 11.00000 0.02313 0.02716 = 0.01992 -0.00163 -0.00607 0.00680 AFIX 43 H1 2 0.218261 0.209739 0.027987 11.00000 -1.20000 AFIX 0 N2 4 0.433943 0.115338 0.140213 11.00000 0.02189 0.02335 = 0.02360 0.00117 -0.00556 0.00651 AFIX 43 H2A 2 0.501292 0.019925 0.153390 11.00000 -1.20000 AFIX 0 O1 5 0.639951 0.743330 0.156840 11.00000 0.02714 0.02554 = 0.02453 -0.00422 -0.00484 0.00714 O2 5 0.591145 0.573055 0.062418 11.00000 0.02780 0.03033 = 0.02388 -0.00464 -0.00925 0.01392 AFIX 147 H2 2 0.533602 0.683978 0.059073 11.00000 -1.50000 AFIX 0 O3 5 0.854672 0.586693 0.228944 11.00000 0.02842 0.02856 = 0.02315 -0.00457 -0.00772 0.00652 AFIX 147 H3 2 0.786019 0.673049 0.219802 11.00000 -1.50000 AFIX 0 O4 5 0.902993 -0.133672 0.051020 11.00000 0.02864 0.02777 = 0.03131 -0.00671 -0.00902 0.01227 AFIX 147 H4A 2 0.973753 -0.215657 0.059544 11.00000 -1.50000 AFIX 0 O5 5 0.396392 -0.096759 0.048618 11.00000 0.03161 0.03308 = 0.02867 -0.00827 -0.00840 0.01470 O6 5 0.127236 0.570212 0.076112 11.00000 0.02836 0.03113 = 0.03477 0.00096 -0.00561 0.01240 HKLF 4 REM exp_10835 in P2(1)/n REM R1 = 0.0393 for 1712 Fo > 4sig(Fo) and 0.0469 for all 1995 data REM 184 parameters refined using 0 restraints END WGHT 0.0601 0.2862 REM Highest difference peak 0.216, deepest hole -0.346, 1-sigma level 0.079 Q1 1 0.9204 -0.0755 -0.0103 11.00000 0.05 0.22 Q2 1 0.2262 0.4498 -0.0112 11.00000 0.05 0.20 Q3 1 0.9342 0.0777 0.2548 11.00000 0.05 0.20 Q4 1 1.1473 0.4252 0.2593 11.00000 0.05 0.19 Q5 1 0.8872 0.0330 0.2514 11.00000 0.05 0.19 ; _shelx_res_checksum 53595 _olex2_submission_special_instructions 'No special instructions were received' 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 C1 C 0.66426(17) 0.5891(3) 0.11724(8) 0.0212(4) Uani 1 1 d . . . . . C2 C 0.77556(17) 0.4046(3) 0.12811(8) 0.0201(4) Uani 1 1 d . . . . . C3 C 0.86487(18) 0.4142(3) 0.18380(8) 0.0212(4) Uani 1 1 d . . . . . C4 C 0.96975(18) 0.2389(3) 0.19308(8) 0.0236(4) Uani 1 1 d . . . . . H4 H 1.030742 0.244786 0.229179 0.028 Uiso 1 1 calc R . . . . C5 C 0.98475(18) 0.0569(3) 0.14969(8) 0.0236(4) Uani 1 1 d . . . . . H5 H 1.054664 -0.059820 0.156935 0.028 Uiso 1 1 calc R . . . . C6 C 0.89518(18) 0.0474(3) 0.09487(8) 0.0222(4) Uani 1 1 d . . . . . C7 C 0.79246(17) 0.2218(3) 0.08399(8) 0.0222(4) Uani 1 1 d . . . . . H7 H 0.734129 0.217592 0.047045 0.027 Uiso 1 1 calc R . . . . C8 C 0.36699(18) 0.0736(3) 0.08241(8) 0.0232(4) Uani 1 1 d . . . . . C9 C 0.39818(18) 0.3031(3) 0.17807(8) 0.0243(4) Uani 1 1 d . . . . . H9 H 0.444906 0.322943 0.217607 0.029 Uiso 1 1 calc R . . . . C10 C 0.29634(18) 0.4575(3) 0.15831(8) 0.0248(4) Uani 1 1 d . . . . . C11 C 0.22017(17) 0.4335(3) 0.09719(8) 0.0227(4) Uani 1 1 d . . . . . F1 F 0.25872(12) 0.6435(2) 0.19448(5) 0.0375(3) Uani 1 1 d . . . . . N1 N 0.26231(15) 0.2351(3) 0.06407(7) 0.0238(3) Uani 1 1 d . . . . . H1 H 0.218261 0.209739 0.027987 0.029 Uiso 1 1 calc R . . . . N2 N 0.43394(15) 0.1153(3) 0.14021(7) 0.0233(3) Uani 1 1 d . . . . . H2A H 0.501292 0.019925 0.153390 0.028 Uiso 1 1 calc R . . . . O1 O 0.63995(13) 0.7433(2) 0.15684(6) 0.0261(3) Uani 1 1 d . . . . . O2 O 0.59114(13) 0.5731(2) 0.06242(6) 0.0279(3) Uani 1 1 d . . . . . H2 H 0.533602 0.683978 0.059073 0.042 Uiso 1 1 calc GR . . . . O3 O 0.85467(14) 0.5867(2) 0.22894(6) 0.0272(3) Uani 1 1 d . . . . . H3 H 0.786019 0.673049 0.219802 0.041 Uiso 1 1 calc GR . . . . O4 O 0.90299(14) -0.1337(2) 0.05102(6) 0.0298(3) Uani 1 1 d . . . . . H4A H 0.973753 -0.215657 0.059544 0.045 Uiso 1 1 calc GR . . . . O5 O 0.39639(14) -0.0968(3) 0.04862(6) 0.0316(3) Uani 1 1 d . . . . . O6 O 0.12724(14) 0.5702(3) 0.07611(6) 0.0318(3) 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 0.0202(8) 0.0226(9) 0.0203(8) 0.0014(7) -0.0024(6) -0.0002(7) C2 0.0187(8) 0.0197(8) 0.0213(8) 0.0026(7) -0.0016(6) 0.0011(7) C3 0.0218(8) 0.0212(9) 0.0202(8) 0.0009(7) -0.0010(6) -0.0009(7) C4 0.0215(8) 0.0276(9) 0.0206(8) 0.0042(7) -0.0054(6) 0.0007(7) C5 0.0204(8) 0.0228(9) 0.0270(9) 0.0068(7) -0.0026(7) 0.0033(7) C6 0.0215(8) 0.0208(9) 0.0239(8) 0.0000(7) -0.0009(6) 0.0022(7) C7 0.0211(8) 0.0233(9) 0.0214(8) 0.0014(7) -0.0042(6) 0.0015(7) C8 0.0209(8) 0.0242(9) 0.0240(8) 0.0009(8) -0.0025(6) 0.0036(7) C9 0.0224(8) 0.0263(9) 0.0233(8) -0.0019(7) -0.0052(7) 0.0008(7) C10 0.0240(8) 0.0227(9) 0.0271(9) -0.0059(7) -0.0019(7) 0.0020(7) C11 0.0195(8) 0.0221(9) 0.0261(8) 0.0016(7) -0.0013(7) 0.0027(7) F1 0.0374(6) 0.0343(7) 0.0389(6) -0.0170(5) -0.0108(5) 0.0130(5) N1 0.0231(7) 0.0272(8) 0.0199(7) -0.0016(6) -0.0061(5) 0.0068(6) N2 0.0219(7) 0.0234(8) 0.0236(7) 0.0012(6) -0.0056(6) 0.0065(6) O1 0.0271(6) 0.0255(7) 0.0245(6) -0.0042(5) -0.0048(5) 0.0071(5) O2 0.0278(7) 0.0303(7) 0.0239(6) -0.0046(5) -0.0093(5) 0.0139(5) O3 0.0284(7) 0.0286(7) 0.0232(6) -0.0046(6) -0.0077(5) 0.0065(5) O4 0.0286(7) 0.0278(7) 0.0313(7) -0.0067(6) -0.0090(5) 0.0123(6) O5 0.0316(7) 0.0331(7) 0.0287(7) -0.0083(6) -0.0084(5) 0.0147(6) O6 0.0284(7) 0.0311(8) 0.0348(7) 0.0010(6) -0.0056(5) 0.0124(6) 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 O1 C1 C2 122.45(14) . . ? O1 C1 O2 122.70(15) . . ? O2 C1 C2 114.84(15) . . ? C3 C2 C1 119.27(15) . . ? C7 C2 C1 120.55(14) . . ? C7 C2 C3 120.19(15) . . ? C4 C3 C2 118.40(16) . . ? O3 C3 C2 123.50(16) . . ? O3 C3 C4 118.09(14) . . ? C3 C4 H4 119.4 . . ? C5 C4 C3 121.14(15) . . ? C5 C4 H4 119.4 . . ? C4 C5 H5 119.9 . . ? C4 C5 C6 120.12(16) . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 119.83(16) . . ? O4 C6 C5 122.47(16) . . ? O4 C6 C7 117.69(15) . . ? C2 C7 H7 119.9 . . ? C6 C7 C2 120.30(15) . . ? C6 C7 H7 119.9 . . ? N2 C8 N1 115.48(16) . . ? O5 C8 N1 121.37(15) . . ? O5 C8 N2 123.15(16) . . ? C10 C9 H9 120.0 . . ? C10 C9 N2 120.08(15) . . ? N2 C9 H9 120.0 . . ? C9 C10 C11 121.97(17) . . ? C9 C10 F1 121.44(15) . . ? F1 C10 C11 116.58(15) . . ? N1 C11 C10 112.82(15) . . ? O6 C11 C10 125.11(17) . . ? O6 C11 N1 122.06(16) . . ? C8 N1 C11 126.98(14) . . ? C8 N1 H1 116.5 . . ? C11 N1 H1 116.5 . . ? C8 N2 C9 122.62(15) . . ? C8 N2 H2A 118.7 . . ? C9 N2 H2A 118.7 . . ? C1 O2 H2 109.5 . . ? C3 O3 H3 109.5 . . ? C6 O4 H4A 109.5 . . ? 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 C1 C2 1.474(2) . ? C1 O1 1.231(2) . ? C1 O2 1.318(2) . ? C2 C3 1.410(2) . ? C2 C7 1.394(3) . ? C3 C4 1.392(3) . ? C3 O3 1.360(2) . ? C4 H4 0.9300 . ? C4 C5 1.378(3) . ? C5 H5 0.9300 . ? C5 C6 1.396(2) . ? C6 C7 1.378(2) . ? C6 O4 1.372(2) . ? C7 H7 0.9300 . ? C8 N1 1.371(2) . ? C8 N2 1.364(2) . ? C8 O5 1.227(2) . ? C9 H9 0.9300 . ? C9 C10 1.335(3) . ? C9 N2 1.369(2) . ? C10 C11 1.450(2) . ? C10 F1 1.345(2) . ? C11 N1 1.376(2) . ? C11 O6 1.222(2) . ? N1 H1 0.8600 . ? N2 H2A 0.8600 . ? O2 H2 0.8200 . ? O3 H3 0.8200 . ? O4 H4A 0.8200 . ? 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 N1 H1 O4 0.86 2.01 2.8707(18) 173.3 3_655 N2 H2A O1 0.86 2.01 2.8399(19) 160.9 1_545 O2 H2 O5 0.82 1.78 2.5977(18) 174.3 1_565 O3 H3 O1 0.82 1.90 2.6124(16) 144.6 . O4 H4A O6 0.82 1.89 2.7078(17) 174.7 1_645 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 C1 C2 C3 C4 -179.72(16) . . . . ? C1 C2 C3 O3 -0.1(3) . . . . ? C1 C2 C7 C6 -178.93(16) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C3 C2 C7 C6 0.9(3) . . . . ? C3 C4 C5 C6 0.8(3) . . . . ? C4 C5 C6 C7 0.6(3) . . . . ? C4 C5 C6 O4 -178.12(16) . . . . ? C5 C6 C7 C2 -1.4(3) . . . . ? C7 C2 C3 C4 0.4(3) . . . . ? C7 C2 C3 O3 -179.94(16) . . . . ? C9 C10 C11 N1 1.4(3) . . . . ? C9 C10 C11 O6 -179.09(19) . . . . ? C10 C9 N2 C8 -1.6(3) . . . . ? C10 C11 N1 C8 -2.1(3) . . . . ? F1 C10 C11 N1 -178.24(15) . . . . ? F1 C10 C11 O6 1.2(3) . . . . ? N1 C8 N2 C9 1.0(3) . . . . ? N2 C8 N1 C11 1.0(3) . . . . ? N2 C9 C10 C11 0.2(3) . . . . ? N2 C9 C10 F1 179.90(16) . . . . ? O1 C1 C2 C3 -4.8(3) . . . . ? O1 C1 C2 C7 175.05(16) . . . . ? O2 C1 C2 C3 176.48(16) . . . . ? O2 C1 C2 C7 -3.7(2) . . . . ? O3 C3 C4 C5 179.06(16) . . . . ? O4 C6 C7 C2 177.33(16) . . . . ? O5 C8 N1 C11 -179.46(17) . . . . ? O5 C8 N2 C9 -178.57(17) . . . . ? O6 C11 N1 C8 178.41(18) . . . . ?