#------------------------------------------------------------------------------ #$Date: 2020-04-24 01:49:31 +0300 (Fri, 24 Apr 2020) $ #$Revision: 251114 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240384.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_7240384 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, 2(H2 O)' _chemical_formula_sum 'C11 H13 F N2 O8' _chemical_formula_weight 320.23 _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 mixed _atom_sites_solution_primary direct _audit_creation_date 2019-09-03 _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 103.754(5) _cell_angle_beta 102.275(5) _cell_angle_gamma 108.186(5) _cell_formula_units_Z 2 _cell_length_a 7.2314(4) _cell_length_b 9.9761(6) _cell_length_c 10.2732(5) _cell_measurement_reflns_used 4295 _cell_measurement_temperature 150(10) _cell_measurement_theta_max 65.3760 _cell_measurement_theta_min 4.6270 _cell_volume 650.04(7) _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 'XS (Sheldrick, 2008)' _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 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -35.00 67.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.7938 -38.0000 -60.0000 102 #__ type_ start__ end____ width___ exp.time_ 2 omega 14.00 117.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.7938 38.0000 120.0000 103 #__ type_ start__ end____ width___ exp.time_ 3 omega 44.00 124.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.7938 167.0000 -28.0000 80 #__ type_ start__ end____ width___ exp.time_ 4 omega -158.00 -94.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 -126.0000 -180.0000 64 #__ type_ start__ end____ width___ exp.time_ 5 omega -122.00 -19.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 126.0000 -150.0000 103 #__ type_ start__ end____ width___ exp.time_ 6 omega -69.00 -5.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 30.0000 -180.0000 64 #__ type_ start__ end____ width___ exp.time_ 7 omega -122.00 -19.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 126.0000 90.0000 103 #__ type_ start__ end____ width___ exp.time_ 8 omega 63.00 165.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 45.0000 -30.0000 102 #__ type_ start__ end____ width___ exp.time_ 9 omega 60.00 165.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 61.0000 60.0000 105 #__ type_ start__ end____ width___ exp.time_ 10 omega 16.00 121.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 -61.0000 90.0000 105 #__ type_ start__ end____ width___ exp.time_ 11 omega 7.00 84.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 -95.0000 0.0000 77 #__ type_ start__ end____ width___ exp.time_ 12 omega 16.00 97.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 -126.0000 120.0000 81 #__ type_ start__ end____ width___ exp.time_ 13 omega 57.00 169.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 77.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 14 omega 11.00 115.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.7938 57.0000 -120.0000 104 #__ type_ start__ end____ width___ exp.time_ 15 omega 7.00 120.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.7938 77.0000 -30.0000 113 #__ type_ start__ end____ width___ exp.time_ 16 omega 11.00 115.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 40.7938 57.0000 150.0000 104 #__ type_ start__ end____ width___ exp.time_ 17 omega -162.00 -49.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 90.0000 113 #__ type_ start__ end____ width___ exp.time_ 18 omega -162.00 -49.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 -30.0000 113 #__ type_ start__ end____ width___ exp.time_ 19 omega -162.00 -49.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 -90.0000 113 #__ type_ start__ end____ width___ exp.time_ 20 omega -162.00 -49.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 150.0000 113 #__ type_ start__ end____ width___ exp.time_ 21 omega -162.00 -49.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - -83.0000 -77.0000 -150.0000 113 #__ type_ start__ end____ width___ exp.time_ 22 omega 16.00 73.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 -45.0000 -30.0000 57 #__ type_ start__ end____ width___ exp.time_ 23 omega 60.00 165.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 61.0000 120.0000 105 #__ type_ start__ end____ width___ exp.time_ 24 omega 60.00 165.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 61.0000 -120.0000 105 #__ type_ start__ end____ width___ exp.time_ 25 omega 63.00 165.00 1.0000 2.0850 omega____ theta____ kappa____ phi______ frames - 90.6218 45.0000 -180.0000 102 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0840556000 _diffrn_orient_matrix_UB_12 -0.1465082000 _diffrn_orient_matrix_UB_13 -0.1248510000 _diffrn_orient_matrix_UB_21 -0.0386455000 _diffrn_orient_matrix_UB_22 -0.0901679000 _diffrn_orient_matrix_UB_23 0.1009729000 _diffrn_orient_matrix_UB_31 -0.2170255000 _diffrn_orient_matrix_UB_32 0.0013433000 _diffrn_orient_matrix_UB_33 -0.0245044000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10247 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 63.677 _diffrn_reflns_theta_max 63.677 _diffrn_reflns_theta_min 4.662 _diffrn_source 'sealed X-ray tube' _diffrn_source_type 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.315 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.57840 _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 1.636 _exptl_crystal_description block _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _refine_diff_density_max 0.311 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.174 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 212 _refine_ls_number_reflns 2111 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.097 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0404 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.1328P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0988 _refine_ls_wR_factor_ref 0.1075 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1783 _reflns_number_total 2111 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00409j2.cif _cod_data_source_block 5FU-34DHBA-2H2O _cod_original_cell_volume 650.05(7) _cod_database_code 7240384 _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_max 0.962 _shelx_estimated_absorpt_t_min 0.880 _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 61.08 _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, All O(H,H) groups 2.a Free rotating group: O8(H8A,H8B), O7(H7A) 2.b Aromatic/amide H refined with riding coordinates: N2(H2B), N1(H1), C9(H9), C6(H6), C5(H5), C2(H2A) 2.c Idealised tetrahedral OH refined as rotating group: O4(H4), O3(H3), O2(H2) ; _shelx_res_file ; TITL exp_10257 in P-1 #2 exp_10257.res created by SHELXL-2016/6 at 18:28:34 on 03-Sep-2019 REM reset to P-1 #2 CELL 1.54184 7.231448 9.976129 10.273217 103.7543 102.2754 108.1856 ZERR 2 0.000425 0.000556 0.000527 0.0046 0.0047 0.0051 LATT 1 SFAC C H F N O UNIT 22 26 2 4 16 EQIV $1 2-X,4-Y,2-Z EQIV $2 1+X,1+Y,1+Z EQIV $3 -X,2-Y,1-Z EQIV $4 -X,1-Y,1-Z EQIV $5 +X,-1+Y,+Z L.S. 4 0 0 PLAN 20 SIZE 0.1 0.05 0.03 HTAB O4 O1_$1 HTAB O3 O8_$2 HTAB N2 O6_$3 HTAB O8 O6_$4 HTAB O7 O5_$5 HTAB N1 O4 HTAB N1 O3 HTAB O8 O7 BOND $H CONF fmap 2 53 acta SHEL 99 0.86 REM REM REM WGHT 0.063700 0.132800 FVAR 7.07444 F1 3 0.296018 0.942763 0.884078 11.00000 0.03102 0.02333 = 0.02637 0.01493 0.00062 0.00521 O4 5 0.773281 1.618092 0.939460 11.00000 0.02376 0.01733 = 0.01729 0.00610 -0.00322 0.00187 AFIX 147 H4 2 0.756838 1.672162 0.892902 11.00000 -1.50000 AFIX 0 O3 5 0.853108 1.477478 1.117197 11.00000 0.02583 0.01490 = 0.02079 0.00680 0.00019 0.00371 AFIX 147 H3 2 0.899795 1.441098 1.173407 11.00000 -1.50000 AFIX 0 N2 4 0.242916 1.144173 0.643607 11.00000 0.01934 0.01940 = 0.01565 0.00704 0.00163 0.00635 AFIX 43 H2B 2 0.169120 1.130369 0.560333 11.00000 -1.20000 AFIX 0 O5 5 0.425329 1.383162 0.661840 11.00000 0.03321 0.01963 = 0.03037 0.01231 0.00533 0.00594 O2 5 1.451882 2.153942 1.385628 11.00000 0.03068 0.01668 = 0.02412 0.00723 -0.00692 -0.00222 AFIX 147 H2 2 1.510911 2.243219 1.399451 11.00000 -1.50000 AFIX 0 N1 4 0.503283 1.303567 0.847880 11.00000 0.01794 0.01488 = 0.02067 0.00298 0.00249 0.00251 AFIX 43 H1 2 0.595150 1.390388 0.897894 11.00000 -1.20000 AFIX 0 O1 5 1.279989 2.161774 1.181516 11.00000 0.03155 0.02050 = 0.02491 0.01079 -0.00350 0.00383 C3 1 0.927014 1.701393 1.063538 11.00000 0.01479 0.01736 = 0.01431 0.00283 0.00204 0.00464 C9 1 0.474639 1.191308 0.905674 11.00000 0.01779 0.02351 = 0.01773 0.00697 0.00321 0.00755 AFIX 43 H9 2 0.555276 1.208957 0.996297 11.00000 -1.20000 AFIX 0 C6 1 1.230623 1.856602 1.323385 11.00000 0.01712 0.01999 = 0.01608 0.00476 0.00141 0.00567 AFIX 43 H6 2 1.330824 1.908495 1.410588 11.00000 -1.20000 AFIX 0 C10 1 0.330391 1.056476 0.831229 11.00000 0.01964 0.01948 = 0.02017 0.01044 0.00579 0.00826 C5 1 1.117808 1.705396 1.288015 11.00000 0.02076 0.01852 = 0.01929 0.00910 0.00426 0.00781 AFIX 43 H5 2 1.143261 1.656302 1.352076 11.00000 -1.20000 AFIX 0 C7 1 1.310147 2.092264 1.260813 11.00000 0.01696 0.02043 = 0.01676 0.00565 0.00206 0.00654 C1 1 1.193194 1.930675 1.227545 11.00000 0.01612 0.01760 = 0.01788 0.00565 0.00456 0.00669 C11 1 0.198965 1.024576 0.691718 11.00000 0.01610 0.01718 = 0.01925 0.00606 0.00651 0.00716 C2 1 1.041110 1.851447 1.097921 11.00000 0.01883 0.01880 = 0.01653 0.00811 0.00440 0.00826 AFIX 43 H2A 2 1.016236 1.900495 1.033709 11.00000 -1.20000 AFIX 0 C4 1 0.967947 1.626242 1.159004 11.00000 0.01858 0.01514 = 0.02008 0.00458 0.00617 0.00577 C8 1 0.393285 1.284235 0.715095 11.00000 0.01741 0.01740 = 0.02204 0.00563 0.00558 0.00602 AFIX 6 O8 5 -0.004448 0.362803 0.315732 11.00000 0.03693 0.01637 = 0.03076 0.00833 -0.00312 0.00265 H8A 2 0.102026 0.424982 0.382429 11.00000 -1.50000 H8B 2 -0.025725 0.275252 0.319709 11.00000 -1.50000 AFIX 6 O7 5 0.291168 0.572167 0.564260 11.00000 0.02963 0.02356 = 0.03358 0.01391 -0.00097 0.00548 H7A 2 0.338754 0.515647 0.598225 11.00000 -1.50000 AFIX 0 O6 5 0.058129 0.903482 0.620456 11.00000 0.02084 0.01679 = 0.01995 0.00491 0.00120 0.00322 H7B 2 0.196173 0.590328 0.600675 11.00000 0.10715 HKLF 4 REM exp_10257 in P-1 #2 REM R1 = 0.0404 for 1783 Fo > 4sig(Fo) and 0.0484 for all 2111 data REM 212 parameters refined using 0 restraints END WGHT 0.0637 0.1328 REM Highest difference peak 0.311, deepest hole -0.544, 1-sigma level 0.174 Q1 1 0.9622 1.6389 1.3916 11.00000 0.05 0.31 Q2 1 0.8151 1.6551 1.2440 11.00000 0.05 0.31 Q3 1 0.8322 1.6454 1.2697 11.00000 0.05 0.31 Q4 1 0.8213 1.4961 0.8596 11.00000 0.05 0.30 Q5 1 0.3175 0.3825 0.3945 11.00000 0.05 0.30 Q6 1 0.4690 1.5557 0.9119 11.00000 0.05 0.30 Q7 1 0.1821 1.1384 0.8558 11.00000 0.05 0.30 Q8 1 1.1280 1.9592 1.3970 11.00000 0.05 0.30 Q9 1 1.1905 1.7243 1.0459 11.00000 0.05 0.29 Q10 1 0.4797 1.2966 0.5651 11.00000 0.05 0.29 Q11 1 1.3954 1.8987 1.1857 11.00000 0.05 0.29 Q12 1 0.7981 1.3564 0.8687 11.00000 0.05 0.29 Q13 1 0.3567 0.6811 0.7861 11.00000 0.05 0.29 Q14 1 0.7182 1.4610 0.7421 11.00000 0.05 0.29 Q15 1 1.0198 1.4962 1.0559 11.00000 0.05 0.29 Q16 1 0.8594 1.4514 0.9153 11.00000 0.05 0.29 Q17 1 1.2833 1.6960 1.1992 11.00000 0.05 0.29 Q18 1 1.3999 2.3178 1.4792 11.00000 0.05 0.28 Q19 1 0.7408 1.7099 1.1203 11.00000 0.05 0.28 Q20 1 1.6199 2.2187 1.2413 11.00000 0.05 0.28 ; _shelx_res_checksum 62450 _olex2_submission_special_instructions 'No special instructions were received' 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 0.29602(17) 0.94276(11) 0.88408(11) 0.0283(3) Uani 1 1 d . . . . . O4 O 0.77328(19) 1.61809(13) 0.93946(12) 0.0225(3) Uani 1 1 d . . . . . H4 H 0.756838 1.672162 0.892902 0.034 Uiso 1 1 calc GR . . . . O3 O 0.85311(19) 1.47748(12) 1.11720(12) 0.0226(3) Uani 1 1 d . . . . . H3 H 0.899795 1.441098 1.173407 0.034 Uiso 1 1 calc GR . . . . N2 N 0.2429(2) 1.14417(15) 0.64361(14) 0.0188(3) Uani 1 1 d . . . . . H2B H 0.169120 1.130369 0.560333 0.023 Uiso 1 1 calc R . . . . O5 O 0.4253(2) 1.38316(13) 0.66184(13) 0.0288(3) Uani 1 1 d . . . . . O2 O 1.4519(2) 2.15394(14) 1.38563(13) 0.0292(4) Uani 1 1 d . . . . . H2 H 1.510911 2.243219 1.399451 0.044 Uiso 1 1 calc GR . . . . N1 N 0.5033(2) 1.30357(15) 0.84788(15) 0.0199(4) Uani 1 1 d . . . . . H1 H 0.595150 1.390388 0.897894 0.024 Uiso 1 1 calc R . . . . O1 O 1.2800(2) 2.16177(14) 1.18152(13) 0.0287(3) Uani 1 1 d . . . . . C3 C 0.9270(3) 1.70139(18) 1.06354(16) 0.0167(4) Uani 1 1 d . . . . . C9 C 0.4746(3) 1.1913(2) 0.90567(18) 0.0201(4) Uani 1 1 d . . . . . H9 H 0.555276 1.208957 0.996297 0.024 Uiso 1 1 calc R . . . . C6 C 1.2306(3) 1.85660(19) 1.32339(18) 0.0190(4) Uani 1 1 d . . . . . H6 H 1.330824 1.908495 1.410588 0.023 Uiso 1 1 calc R . . . . C10 C 0.3304(3) 1.05648(19) 0.83123(18) 0.0189(4) Uani 1 1 d . . . . . C5 C 1.1178(3) 1.70540(19) 1.28801(18) 0.0192(4) Uani 1 1 d . . . . . H5 H 1.143261 1.656302 1.352076 0.023 Uiso 1 1 calc R . . . . C7 C 1.3101(3) 2.09226(19) 1.26081(17) 0.0188(4) Uani 1 1 d . . . . . C1 C 1.1932(3) 1.93067(19) 1.22754(17) 0.0173(4) Uani 1 1 d . . . . . C11 C 0.1990(3) 1.02458(18) 0.69172(17) 0.0171(4) Uani 1 1 d . . . . . C2 C 1.0411(3) 1.85145(19) 1.09792(17) 0.0175(4) Uani 1 1 d . . . . . H2A H 1.016236 1.900495 1.033709 0.021 Uiso 1 1 calc R . . . . C4 C 0.9679(3) 1.62624(19) 1.15900(18) 0.0183(4) Uani 1 1 d . . . . . C8 C 0.3933(3) 1.28423(19) 0.71510(18) 0.0194(4) Uani 1 1 d . . . . . O8 O -0.0044(2) 0.36280(15) 0.31573(14) 0.0322(4) Uani 1 1 d . . . . . H8A H 0.102026 0.424982 0.382429 0.048 Uiso 1 1 d G . . . . H8B H -0.025725 0.275252 0.319709 0.048 Uiso 1 1 d G . . . . O7 O 0.2912(2) 0.57217(15) 0.56426(15) 0.0311(4) Uani 1 1 d . . . . . H7A H 0.338754 0.515647 0.598225 0.047 Uiso 1 1 d G . . . . O6 O 0.05813(19) 0.90348(13) 0.62046(12) 0.0213(3) Uani 1 1 d . . . . . H7B H 0.196(6) 0.590(4) 0.601(4) 0.107(14) 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 0.0310(7) 0.0233(6) 0.0264(6) 0.0149(5) 0.0006(5) 0.0052(5) O4 0.0238(7) 0.0173(6) 0.0173(6) 0.0061(5) -0.0032(5) 0.0019(5) O3 0.0258(8) 0.0149(6) 0.0208(6) 0.0068(5) 0.0002(5) 0.0037(5) N2 0.0193(8) 0.0194(7) 0.0157(7) 0.0070(6) 0.0016(6) 0.0064(6) O5 0.0332(8) 0.0196(7) 0.0304(7) 0.0123(6) 0.0053(6) 0.0059(6) O2 0.0307(8) 0.0167(7) 0.0241(7) 0.0072(5) -0.0069(6) -0.0022(6) N1 0.0179(8) 0.0149(7) 0.0207(7) 0.0030(6) 0.0025(6) 0.0025(6) O1 0.0316(8) 0.0205(7) 0.0249(7) 0.0108(5) -0.0035(6) 0.0038(6) C3 0.0148(9) 0.0174(9) 0.0143(8) 0.0028(7) 0.0020(7) 0.0046(7) C9 0.0178(10) 0.0235(9) 0.0177(8) 0.0070(7) 0.0032(7) 0.0075(8) C6 0.0171(10) 0.0200(9) 0.0161(8) 0.0048(7) 0.0014(7) 0.0057(7) C10 0.0196(10) 0.0195(9) 0.0202(9) 0.0104(7) 0.0058(7) 0.0083(8) C5 0.0208(10) 0.0185(9) 0.0193(9) 0.0091(7) 0.0043(7) 0.0078(8) C7 0.0170(10) 0.0204(9) 0.0168(8) 0.0056(7) 0.0021(7) 0.0065(8) C1 0.0161(9) 0.0176(9) 0.0179(8) 0.0056(7) 0.0046(7) 0.0067(7) C11 0.0161(9) 0.0172(9) 0.0192(8) 0.0061(7) 0.0065(7) 0.0072(8) C2 0.0188(10) 0.0188(9) 0.0165(8) 0.0081(7) 0.0044(7) 0.0083(7) C4 0.0186(10) 0.0151(8) 0.0201(8) 0.0046(7) 0.0062(7) 0.0058(7) C8 0.0174(10) 0.0174(9) 0.0220(9) 0.0056(7) 0.0056(7) 0.0060(7) O8 0.0369(9) 0.0164(6) 0.0308(7) 0.0083(6) -0.0031(6) 0.0027(6) O7 0.0296(9) 0.0236(7) 0.0336(8) 0.0139(6) -0.0010(6) 0.0055(6) O6 0.0208(7) 0.0168(6) 0.0200(6) 0.0049(5) 0.0012(5) 0.0032(5) 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 C3 O4 H4 109.5 . . ? C4 O3 H3 109.5 . . ? C11 N2 H2B 116.7 . . ? C11 N2 C8 126.62(15) . . ? C8 N2 H2B 116.7 . . ? C7 O2 H2 109.5 . . ? C9 N1 H1 118.5 . . ? C8 N1 H1 118.5 . . ? C8 N1 C9 123.07(15) . . ? O4 C3 C2 123.78(15) . . ? O4 C3 C4 116.62(14) . . ? C2 C3 C4 119.60(16) . . ? N1 C9 H9 120.2 . . ? C10 C9 N1 119.59(16) . . ? C10 C9 H9 120.2 . . ? C5 C6 H6 120.2 . . ? C5 C6 C1 119.67(16) . . ? C1 C6 H6 120.2 . . ? F1 C10 C11 116.08(15) . . ? C9 C10 F1 121.66(15) . . ? C9 C10 C11 122.24(16) . . ? C6 C5 H5 119.5 . . ? C4 C5 C6 121.07(16) . . ? C4 C5 H5 119.5 . . ? O2 C7 C1 113.24(15) . . ? O1 C7 O2 123.06(16) . . ? O1 C7 C1 123.70(16) . . ? C6 C1 C7 121.53(16) . . ? C2 C1 C6 119.38(16) . . ? C2 C1 C7 119.08(15) . . ? N2 C11 C10 113.22(15) . . ? O6 C11 N2 121.93(15) . . ? O6 C11 C10 124.85(15) . . ? C3 C2 C1 120.92(16) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? O3 C4 C3 116.65(15) . . ? O3 C4 C5 124.03(15) . . ? C5 C4 C3 119.32(15) . . ? O5 C8 N2 122.01(16) . . ? O5 C8 N1 122.79(16) . . ? N1 C8 N2 115.20(15) . . ? H8A O8 H8B 109.4 . . ? H7A O7 H7B 112.4 . . ? 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 C10 1.348(2) . ? O4 H4 0.8200 . ? O4 C3 1.367(2) . ? O3 H3 0.8200 . ? O3 C4 1.361(2) . ? N2 H2B 0.8600 . ? N2 C11 1.371(2) . ? N2 C8 1.378(2) . ? O5 C8 1.223(2) . ? O2 H2 0.8200 . ? O2 C7 1.321(2) . ? N1 H1 0.8600 . ? N1 C9 1.369(2) . ? N1 C8 1.360(2) . ? O1 C7 1.216(2) . ? C3 C2 1.378(2) . ? C3 C4 1.406(2) . ? C9 H9 0.9300 . ? C9 C10 1.333(3) . ? C6 H6 0.9300 . ? C6 C5 1.385(3) . ? C6 C1 1.395(2) . ? C10 C11 1.440(2) . ? C5 H5 0.9300 . ? C5 C4 1.383(2) . ? C7 C1 1.482(2) . ? C1 C2 1.393(2) . ? C11 O6 1.236(2) . ? C2 H2A 0.9300 . ? O8 H8A 0.8500 . ? O8 H8B 0.8509 . ? O7 H7A 0.8495 . ? O7 H7B 0.89(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 O4 H4 O1 0.82 2.05 2.8527(17) 167.2 2_797 O3 H3 O8 0.82 1.92 2.7352(17) 174.7 1_666 N2 H2B O6 0.86 2.08 2.9247(19) 167.6 2_576 N1 H1 O4 0.86 2.12 2.9213(18) 155.5 . N1 H1 O3 0.86 2.36 3.0110(19) 132.5 . O8 H8A O7 0.85 1.97 2.7942(19) 163.8 . O8 H8B O6 0.85 1.98 2.8160(17) 165.8 2_566 O7 H7A O5 0.85 1.82 2.6699(18) 175.9 1_545 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 C10 C11 N2 -179.43(14) . . . . ? F1 C10 C11 O6 1.3(3) . . . . ? O4 C3 C2 C1 178.71(16) . . . . ? O4 C3 C4 O3 1.2(2) . . . . ? O4 C3 C4 C5 -178.19(15) . . . . ? O2 C7 C1 C6 1.6(2) . . . . ? O2 C7 C1 C2 -178.96(15) . . . . ? N1 C9 C10 F1 -179.67(15) . . . . ? N1 C9 C10 C11 -1.3(3) . . . . ? O1 C7 C1 C6 -178.59(17) . . . . ? O1 C7 C1 C2 0.8(3) . . . . ? C9 N1 C8 N2 2.7(2) . . . . ? C9 N1 C8 O5 -176.83(17) . . . . ? C9 C10 C11 N2 2.1(2) . . . . ? C9 C10 C11 O6 -177.11(17) . . . . ? C6 C5 C4 O3 179.36(16) . . . . ? C6 C5 C4 C3 -1.3(3) . . . . ? C6 C1 C2 C3 0.2(3) . . . . ? C5 C6 C1 C7 -179.97(16) . . . . ? C5 C6 C1 C2 0.6(3) . . . . ? C7 C1 C2 C3 -179.18(15) . . . . ? C1 C6 C5 C4 -0.1(3) . . . . ? C11 N2 C8 O5 177.79(16) . . . . ? C11 N2 C8 N1 -1.8(3) . . . . ? C2 C3 C4 O3 -178.47(15) . . . . ? C2 C3 C4 C5 2.1(3) . . . . ? C4 C3 C2 C1 -1.6(3) . . . . ? C8 N2 C11 C10 -0.5(2) . . . . ? C8 N2 C11 O6 178.74(16) . . . . ? C8 N1 C9 C10 -1.3(3) . . . . ?