#------------------------------------------------------------------------------ #$Date: 2020-06-30 04:27:46 +0300 (Tue, 30 Jun 2020) $ #$Revision: 253543 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240794.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_7240794 loop_ _publ_author_name 'Wang, Lin-Lin' 'Wang, Ling-Yang' 'Yu, Yueming' 'Li, Yan-Tuan' 'Wu, Zhi-Yong' 'Yan, Cui-Wei' _publ_section_title ; Cocrystallization of 5-fluorouracil and L-phenylalanine: The first zwitterionic cocrystal of 5-fluorouracil with amino acid exhibiting the perfected in vitro/vivo pharmaceutical properties ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00713G _journal_year 2020 _chemical_absolute_configuration rm _chemical_formula_moiety 'C4 H3 F N2 O2, C9 H11 N O2' _chemical_formula_sum 'C13 H14 F N3 O4' _chemical_formula_weight 295.27 _chemical_name_common '5-fluorouracil L-phenylalanine' _chemical_name_systematic '5-Fluoropyrimidine-2,4(1H,3H)-dione 2-ammonio-3-phenylpropanoate' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2016/4 _audit_update_record ; 2019-12-16 deposited with the CCDC. 2020-06-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.00870(10) _cell_length_b 12.3981(2) _cell_length_c 15.1304(3) _cell_measurement_reflns_used 2972 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 72.9370 _cell_measurement_theta_min 4.5780 _cell_volume 1314.75(4) _computing_structure_refinement 'SHELXL-2016/4 (Sheldrick, 2016)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type Bruker _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_unetI/netI 0.0431 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4565 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.965 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.244 _diffrn_reflns_theta_min 4.611 _exptl_absorpt_coefficient_mu 1.038 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.492 _exptl_crystal_description column _exptl_crystal_F_000 616 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethanol/acetone/water' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.182 _refine_diff_density_min -0.290 _refine_diff_density_rms 0.063 _refine_ls_abs_structure_details ; Flack x determined using 944 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.17(14) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 2555 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0320 _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^)+(0.0365P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.0775 _reflns_Friedel_coverage 0.688 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.944 _reflns_number_gt 2421 _reflns_number_total 2555 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00713g1.cif _cod_data_source_block shelx _cod_database_code 7240794 _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 0.746 _shelx_estimated_absorpt_t_max 0.950 _shelx_res_file ; TITL SIR92 run in space group P 21 21 21 shelx.res created by SHELXL-2016/4 at 10:46:53 on 28-Mar-2018 CELL 1.54184 7.0087 12.3981 15.1304 90.000 90.000 90.000 ZERR 4.00 0.0001 0.0002 0.0003 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, - Z SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O F UNIT 52 56 12 16 4 MERG 2 FMAP 2 PLAN 25 SIZE 0.050 0.050 0.300 ACTA BOND $H CONF L.S. 10 TEMP -173.00 WGHT 0.036500 FVAR 0.50762 F1 5 0.455620 0.854222 0.440882 11.00000 0.03616 0.01571 = 0.01214 -0.00446 0.00000 0.00599 O1 4 0.624327 0.537224 0.213678 11.00000 0.02073 0.01319 = 0.01009 0.00013 0.00422 0.00008 O2 4 0.517886 0.643768 0.497281 11.00000 0.02752 0.01897 = 0.00677 0.00203 -0.00002 0.00227 N1 3 0.561319 0.715328 0.238350 11.00000 0.01661 0.01264 = 0.00855 0.00235 0.00016 0.00017 N2 3 0.570487 0.592970 0.354487 11.00000 0.01573 0.01189 = 0.00809 0.00182 0.00140 0.00139 C1 1 0.587859 0.611636 0.264982 11.00000 0.01167 0.01346 = 0.00863 0.00114 0.00091 -0.00021 C2 1 0.528803 0.668517 0.418300 11.00000 0.01363 0.01597 = 0.01011 -0.00044 -0.00037 -0.00012 C3 1 0.500178 0.775249 0.382658 11.00000 0.01895 0.01239 = 0.01106 -0.00354 -0.00089 0.00119 C4 1 0.514054 0.796123 0.296108 11.00000 0.01478 0.01373 = 0.01165 -0.00006 -0.00145 -0.00068 O3 4 0.585040 0.379772 0.398116 11.00000 0.02482 0.01473 = 0.00787 0.00006 0.00080 -0.00209 O4 4 0.412376 0.240783 0.446458 11.00000 0.01916 0.01884 = 0.01262 -0.00389 0.00028 -0.00687 N3 3 0.686006 0.446330 0.556625 11.00000 0.01260 0.01445 = 0.00731 0.00009 -0.00118 -0.00091 C5 1 0.508220 0.325288 0.458185 11.00000 0.01262 0.01476 = 0.00875 -0.00226 -0.00151 0.00211 C6 1 0.534239 0.361959 0.554141 11.00000 0.01304 0.01216 = 0.00799 0.00074 -0.00065 -0.00058 C7 1 0.350839 0.404045 0.597079 11.00000 0.01224 0.02147 = 0.01074 -0.00113 0.00004 0.00030 C8 1 0.378215 0.427325 0.694333 11.00000 0.00974 0.02034 = 0.00926 -0.00067 0.00095 0.00045 C9 1 0.388288 0.532651 0.726108 11.00000 0.01946 0.01679 = 0.01356 -0.00050 0.00171 0.00147 C10 1 0.412627 0.552945 0.815785 11.00000 0.02460 0.02110 = 0.01633 -0.00479 0.00269 -0.00190 C11 1 0.431922 0.468142 0.875028 11.00000 0.01677 0.03055 = 0.01088 -0.00306 -0.00008 -0.00414 C12 1 0.426520 0.362370 0.844291 11.00000 0.01602 0.02374 = 0.01210 0.00353 0.00167 0.00031 C13 1 0.398713 0.342179 0.754556 11.00000 0.01631 0.01727 = 0.01372 0.00009 0.00156 -0.00033 H1 2 0.565278 0.728369 0.175134 11.00000 0.03561 H2 2 0.581061 0.524392 0.373243 11.00000 0.02984 H3A 2 0.629325 0.513990 0.534214 11.00000 0.04251 H3B 2 0.744631 0.455119 0.613130 11.00000 0.02704 H3C 2 0.785850 0.423160 0.521737 11.00000 0.02261 H4 2 0.490413 0.864176 0.268764 11.00000 0.02921 H6 2 0.587103 0.298041 0.588600 11.00000 0.01637 H7A 2 0.246789 0.348229 0.589526 11.00000 0.01020 H7B 2 0.304210 0.472814 0.562538 11.00000 0.02183 H9 2 0.377860 0.588493 0.682240 11.00000 0.02184 H10 2 0.417179 0.629092 0.838214 11.00000 0.04211 H11 2 0.450910 0.481833 0.938206 11.00000 0.02518 H12 2 0.445537 0.300251 0.885173 11.00000 0.03125 H13 2 0.387037 0.265876 0.731379 11.00000 0.02589 HKLF 4 REM SIR92 run in space group P 21 21 21 REM R1 = 0.0320 for 2421 Fo > 4sig(Fo) and 0.0344 for all 2555 data REM 246 parameters refined using 0 restraints END WGHT 0.0365 0.0000 REM Highest difference peak 0.182, deepest hole -0.290, 1-sigma level 0.063 Q1 1 0.7237 0.6385 0.5168 11.00000 0.05 0.18 Q2 1 0.8204 0.5467 0.2156 11.00000 0.05 0.18 Q3 1 0.2213 0.5453 0.7810 11.00000 0.05 0.18 Q4 1 0.7260 0.8673 0.4796 11.00000 0.05 0.16 Q5 1 0.2927 0.2890 0.9790 11.00000 0.05 0.16 Q6 1 0.7482 0.6527 0.4471 11.00000 0.05 0.16 Q7 1 0.2677 0.5833 0.6358 11.00000 0.05 0.15 Q8 1 0.7439 0.3403 0.3614 11.00000 0.05 0.15 Q9 1 0.2262 0.4816 0.9617 11.00000 0.05 0.14 Q10 1 0.7869 0.3727 0.3991 11.00000 0.05 0.14 Q11 1 0.1781 0.6179 0.8221 11.00000 0.05 0.14 Q12 1 0.2469 0.4278 0.9778 11.00000 0.05 0.14 Q13 1 0.2747 0.2960 0.4597 11.00000 0.05 0.14 Q14 1 0.7886 0.7243 0.1903 11.00000 0.05 0.14 Q15 1 0.8194 0.6168 0.2987 11.00000 0.05 0.14 Q16 1 0.6775 0.3584 0.8735 11.00000 0.05 0.14 Q17 1 0.3303 0.7453 0.3400 11.00000 0.05 0.14 Q18 1 0.7516 0.5637 0.4561 11.00000 0.05 0.14 Q19 1 0.2118 0.3364 0.7530 11.00000 0.05 0.14 Q20 1 0.2926 0.1499 0.8084 11.00000 0.05 0.13 Q21 1 0.2589 0.4092 0.8923 11.00000 0.05 0.13 Q22 1 0.7689 0.5745 0.3659 11.00000 0.05 0.13 Q23 1 0.7779 0.6931 0.2592 11.00000 0.05 0.13 Q24 1 0.2158 0.5160 0.6981 11.00000 0.05 0.13 Q25 1 0.2120 0.5555 0.9139 11.00000 0.05 0.13 ; _shelx_res_checksum 98898 _shelx_hkl_file ; 0 0 -2 54.49 1.73 0 0 2 54.38 1.51 0 0 3 -0.04 0.19 0 0 -3 0.38 0.29 0 0 -4 212.48 4.90 0 0 4 209.69 4.32 0 0 5 0.08 0.23 0 0 6 1527.53 14.92 0 0 7 -0.50 0.43 0 0 8 55.28 3.52 0 0 9 0.14 0.24 0 0 10 106.07 5.81 0 0 -11 -2.29 1.28 0 0 11 0.44 0.41 0 0 -12 54.16 6.30 0 0 -13 -1.48 1.24 0 0 -14 16.63 3.73 0 0 -15 -0.09 1.19 0 0 -16 116.67 9.93 0 0 -17 1.01 1.80 0 0 -18 133.90 9.46 0 1 0 0.09 0.07 0 1 -1 3.06 0.37 0 1 -2 21.13 1.18 0 -1 2 19.89 0.96 0 -1 3 251.82 4.11 0 1 -3 262.80 4.93 0 -1 4 170.43 3.90 0 1 -4 175.95 4.68 0 1 -5 57.74 2.98 0 -1 5 54.91 2.54 0 -1 6 2292.93 18.38 0 1 6 2345.63 19.30 0 -1 7 534.72 9.84 0 1 7 529.90 10.20 0 1 -7 543.02 11.01 0 -1 8 351.21 8.68 0 1 8 342.84 8.98 0 1 9 131.50 6.11 0 -1 9 126.91 5.69 0 -1 10 4.45 1.27 0 1 10 2.61 1.00 0 -1 11 18.26 2.55 0 1 11 17.97 2.68 0 1 -11 17.61 3.42 0 1 12 73.12 5.69 0 1 -12 78.70 7.81 0 -1 -12 73.37 7.27 0 -1 -13 197.45 12.33 0 1 -13 212.42 13.53 0 1 -14 126.29 10.76 0 -1 -14 122.54 9.92 0 1 -15 128.04 11.12 0 -1 -15 139.15 10.49 0 1 -16 2.21 2.11 0 -1 -16 -0.06 0.73 0 1 -17 2.89 1.64 0 -1 -17 4.86 1.97 0 -1 -18 14.09 2.90 0 1 -18 11.11 2.64 0 2 0 1.33 0.35 0 2 -1 1667.82 10.77 0 2 -2 573.46 7.01 0 2 -3 89.74 3.09 0 2 -4 129.80 4.20 0 -2 5 18.95 1.52 0 2 -5 17.81 1.72 0 -2 6 190.06 5.29 0 2 -6 197.17 6.39 0 2 -7 100.83 4.96 0 2 7 98.41 4.64 0 -2 7 94.87 4.12 0 -2 8 9.54 1.46 0 2 8 9.32 1.57 0 2 -8 9.50 1.74 0 -2 9 194.05 7.06 0 2 9 189.34 7.62 0 2 10 117.05 6.49 0 2 11 167.01 8.33 0 2 -11 198.32 12.14 0 2 -12 34.82 5.50 0 2 12 37.89 4.23 0 2 -13 0.84 1.07 0 -2 -13 1.66 1.39 0 -2 -14 49.11 6.13 0 2 -14 53.29 7.38 0 -2 -15 57.77 6.59 0 2 -15 61.15 8.07 0 2 -16 24.01 4.87 0 -2 -16 28.39 4.47 0 -2 -17 34.34 4.72 0 2 -17 37.97 5.85 0 2 -18 -2.08 1.33 0 -2 -18 -0.48 0.75 0 3 0 1.12 0.41 0 3 -1 33.59 1.87 0 3 -2 17.28 1.40 0 3 -3 269.83 5.95 0 3 -4 75.75 3.49 0 3 -5 77.76 3.87 0 3 -6 11.17 1.62 0 3 -7 333.54 9.52 0 3 8 40.49 3.45 0 3 -8 40.38 3.57 0 3 9 93.74 5.64 0 3 -9 98.45 5.92 0 3 10 45.15 4.25 0 3 -10 51.35 6.19 0 3 -11 487.03 13.71 0 3 11 467.78 14.50 0 3 12 -0.43 0.74 0 3 -12 0.33 0.50 0 3 -13 448.27 22.29 0 -3 -14 320.19 15.37 0 3 -14 318.54 19.41 0 -3 -15 1.82 1.02 0 3 -15 2.88 2.57 0 -3 -16 0.59 1.00 0 3 -16 2.31 1.45 0 -3 -17 45.56 5.02 0 3 -17 38.10 5.84 0 -3 -18 63.27 5.36 0 3 -18 56.15 5.48 0 4 0 973.15 11.66 0 4 1 195.80 5.36 0 4 -1 197.03 5.21 0 4 -2 595.24 9.34 0 4 -3 547.58 9.50 0 4 -4 45.55 2.89 0 4 -5 9.89 1.46 0 4 -6 3.09 0.97 0 4 -7 189.63 7.55 0 4 -8 16.32 2.37 0 4 9 5.68 1.46 0 4 -9 3.91 1.23 0 4 10 -0.25 0.42 0 4 -10 1.28 0.94 0 4 -10 1.16 0.78 0 4 -10 2.31 1.84 0 4 -11 194.21 14.53 0 4 11 188.86 9.60 0 4 -11 177.26 8.50 0 4 -12 417.00 22.36 0 4 -12 360.84 12.14 0 4 -13 411.05 12.77 0 4 -13 450.59 24.11 0 4 -14 0.69 1.37 0 -4 -15 6.06 2.06 0 4 -15 -0.17 2.14 0 -4 -16 3.09 1.46 0 4 -16 -0.08 1.02 0 4 -17 15.42 3.26 0 -4 -17 16.87 2.93 0 4 -18 0.24 0.55 0 -4 -18 -0.05 0.45 0 5 0 0.12 0.32 0 5 -1 998.89 13.28 0 5 1 961.08 13.53 0 5 -2 183.94 5.84 0 5 -3 49.64 3.18 0 5 -4 522.83 10.84 0 5 -5 799.29 14.47 0 5 -6 1.23 0.67 0 5 -7 486.05 12.88 0 5 -8 65.88 5.06 0 5 -9 171.30 13.63 0 5 9 176.86 8.71 0 5 -9 172.80 8.30 0 5 -9 163.23 8.42 0 5 -10 205.76 9.31 0 5 -10 196.03 9.59 0 5 -10 223.84 16.53 0 5 10 210.59 10.08 0 5 -11 5.85 1.63 0 5 11 6.09 2.01 0 5 -11 5.88 2.46 0 5 -12 64.01 5.27 0 5 -12 62.28 9.31 0 5 -13 137.26 13.96 0 5 -13 145.11 7.69 0 5 -14 58.67 8.89 0 5 -14 50.35 4.24 0 -5 -15 109.82 8.27 0 5 -15 86.65 9.84 0 -5 -16 8.57 2.08 0 5 -16 4.17 1.59 0 -5 -17 38.33 4.03 0 5 -17 33.17 4.19 0 6 0 2.28 0.67 0 6 -1 7.94 1.35 0 6 1 8.25 1.40 0 6 -2 196.30 6.66 0 6 2 190.08 6.89 0 6 -3 274.03 8.22 0 6 -4 269.52 8.50 0 6 -5 228.47 8.25 0 6 -6 17.70 2.44 0 6 -7 51.91 4.44 0 6 -8 1.40 0.83 0 6 -8 2.49 1.18 0 6 -8 1.82 1.18 0 6 -9 41.14 7.10 0 6 9 39.78 4.40 0 6 -9 42.67 4.33 0 6 -9 40.00 4.40 0 6 -10 10.75 2.23 0 6 -10 12.92 2.55 0 6 -10 11.28 3.72 0 6 10 12.16 2.56 0 6 -11 0.17 1.44 0 6 -11 -0.34 0.95 0 6 -12 23.22 5.57 0 6 -12 24.22 3.19 0 6 -13 27.31 6.00 0 6 -13 31.20 3.52 0 6 -14 24.91 5.15 0 -6 -15 15.35 2.99 0 6 -15 10.65 2.98 0 -6 -16 -0.63 0.67 0 6 -16 1.00 0.66 0 6 -17 0.38 0.37 0 -6 -17 0.48 0.68 0 7 0 0.02 0.39 0 7 1 69.68 4.42 0 7 -1 76.24 4.54 0 7 2 227.54 8.17 0 7 -2 243.38 8.22 0 7 3 37.50 3.45 0 7 -3 38.43 3.38 0 7 -4 101.16 5.69 0 7 4 88.65 5.53 0 7 -5 382.13 11.52 0 7 -6 0.82 0.72 0 7 -7 30.47 3.55 0 7 -7 29.67 5.48 0 7 -7 30.32 3.59 0 7 -8 132.72 11.90 0 7 -8 133.33 7.76 0 7 -8 132.71 7.88 0 7 -8 125.81 6.01 0 7 -9 30.68 3.76 0 7 -9 36.49 4.31 0 7 -9 26.25 5.46 0 7 -10 72.46 6.25 0 7 -10 61.54 8.62 0 7 -10 68.40 5.73 0 7 -11 70.65 5.79 0 7 -11 59.84 8.34 0 7 -12 50.43 7.44 0 7 -13 -2.23 2.39 0 7 -14 23.22 4.16 0 7 -15 1.62 1.12 0 -7 -15 1.41 0.90 0 7 -16 3.68 1.29 0 -7 -16 2.44 0.97 0 8 0 87.42 5.29 0 8 1 1.60 0.79 0 8 -1 3.19 1.02 0 8 -2 185.95 7.86 0 8 2 176.96 7.79 0 8 3 6.27 1.54 0 8 -3 6.26 1.54 0 8 -4 20.67 3.53 0 8 4 15.36 2.43 0 8 -4 19.72 2.74 0 8 -5 84.27 7.34 0 8 -5 70.46 5.32 0 8 5 67.23 5.40 0 8 -5 78.73 4.94 0 8 -6 43.55 5.67 0 8 -6 36.37 3.98 0 8 6 28.90 3.59 0 8 -6 37.07 3.43 0 8 -7 28.27 3.61 0 8 -7 23.90 4.49 0 8 -7 30.86 3.16 0 8 -8 100.10 9.24 0 8 -8 97.75 5.60 0 8 -8 102.56 7.22 0 8 -9 25.49 4.84 0 8 -10 34.03 5.73 0 8 -11 99.57 9.32 0 8 -12 34.85 5.31 0 8 -13 3.21 1.66 0 8 -14 -0.26 0.86 0 -8 -15 2.80 1.14 0 8 -15 1.42 0.72 0 8 -16 1.04 0.54 0 9 0 0.08 0.43 0 9 0 -0.48 0.66 0 9 -1 29.51 3.33 0 9 1 30.94 3.36 0 9 -1 28.65 4.13 0 9 1 32.81 4.30 0 9 -1 28.87 3.22 0 9 1 27.66 3.22 0 9 -2 1.36 0.77 0 9 -2 2.36 1.41 0 9 -2 1.09 0.78 0 9 2 0.10 0.36 0 9 2 1.56 0.83 0 9 2 1.65 0.84 0 9 -3 29.76 4.20 0 9 -3 32.11 3.60 0 9 -3 30.74 3.31 0 9 3 31.37 4.25 0 9 3 31.64 3.47 0 9 3 30.73 3.56 0 9 -3 24.17 4.09 0 9 -4 4.51 1.87 0 9 -4 1.80 1.39 0 9 4 0.75 0.56 0 9 -4 1.83 1.03 0 9 -4 1.59 0.91 0 9 4 1.42 0.75 0 9 4 1.19 0.79 0 9 -5 4.07 1.26 0 9 -5 5.57 1.95 0 9 -5 2.55 1.17 0 9 5 3.97 1.57 0 9 -6 0.31 0.55 0 9 -6 0.20 1.35 0 9 -6 0.28 0.67 0 9 6 0.26 0.74 0 9 -7 46.78 4.85 0 9 -7 50.61 6.08 0 9 -7 47.25 4.06 0 9 -8 0.52 0.41 0 9 -8 0.33 0.70 0 9 -9 34.56 3.27 0 9 -9 41.98 5.73 0 9 -10 1.27 1.47 0 9 -11 13.73 3.12 0 9 -12 37.69 4.77 0 9 -13 27.32 3.70 0 9 -14 0.27 0.35 0 -9 -15 4.88 1.11 0 9 -15 5.20 1.41 0 9 -15 6.70 1.35 0 10 0 440.59 13.32 0 10 0 445.10 16.39 0 10 0 413.87 13.13 0 10 -1 1.04 0.59 0 10 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-6 -6 -1 1.81 1.04 6 6 0 39.65 4.64 6 -6 -1 5.79 1.40 6 6 1 0.64 1.19 6 -6 -2 28.23 2.73 6 6 2 19.20 3.21 -6 6 -2 23.69 2.72 6 -6 -3 85.27 4.66 -6 6 -3 83.97 5.25 6 -6 -4 46.11 3.52 6 6 4 34.41 4.09 -6 6 -4 36.32 3.54 -6 6 -5 1.42 0.85 6 6 5 -0.52 1.07 -6 6 -6 13.92 2.12 6 6 6 12.93 2.28 -6 6 -7 35.72 3.32 -6 6 -8 22.96 2.50 -6 6 -9 15.24 1.87 -6 6 -10 12.42 1.52 -6 6 -11 102.56 3.74 -6 -7 -10 12.41 1.68 -6 -7 -9 61.53 4.25 -6 -7 -8 1.84 0.89 6 7 -7 33.54 2.92 -6 -7 -7 35.60 3.76 6 7 -6 8.37 1.85 -6 -7 -6 10.70 2.19 6 7 -5 16.79 2.54 -6 -7 -5 16.60 2.76 6 7 -4 9.23 2.11 -6 -7 -4 7.34 1.90 6 7 -3 61.39 5.41 -6 -7 -3 58.99 5.17 6 7 -2 8.01 2.00 -6 -7 -2 5.67 1.57 6 7 -1 44.12 4.65 -6 -7 -1 31.18 3.69 6 7 0 1.83 1.04 6 7 1 32.39 4.03 6 7 2 7.57 1.92 -6 7 -2 10.34 1.66 6 7 3 53.62 5.09 -6 7 -3 65.67 4.21 -6 7 -4 7.74 1.49 6 7 4 7.26 1.92 6 7 5 20.03 2.92 -6 7 -5 18.84 2.32 -6 7 -6 10.11 1.68 6 7 6 7.59 1.64 -6 7 -7 36.46 2.95 -6 7 -8 1.03 0.57 -6 7 -9 62.60 3.38 -6 7 -10 11.87 1.33 -6 -8 -9 0.06 0.40 -6 -8 -8 10.95 1.76 -6 -8 -7 34.34 3.34 6 8 -6 66.65 4.14 -6 -8 -6 66.17 4.90 6 8 -5 10.24 1.88 -6 -8 -5 9.76 1.97 6 8 -4 14.06 2.33 -6 -8 -4 15.26 2.50 6 8 -3 12.66 2.30 -6 -8 -3 12.41 2.24 6 8 -2 26.04 3.38 -6 -8 -2 20.50 2.94 6 8 -1 34.42 3.90 -6 -8 -1 26.90 3.24 6 8 0 73.13 5.80 6 8 1 38.30 4.21 6 8 2 23.42 3.21 -6 8 -2 25.26 2.34 6 8 3 13.20 2.35 -6 8 -3 12.82 1.68 6 8 4 14.92 2.46 -6 8 -4 18.22 2.07 6 8 5 9.24 1.85 -6 8 -5 9.04 1.41 6 8 6 68.29 4.63 -6 8 -6 68.98 3.81 -6 8 -7 33.09 2.52 -6 8 -8 12.32 1.46 -6 8 -9 0.85 0.44 -6 -9 -8 50.04 3.08 -6 -9 -7 4.19 0.96 -6 -9 -6 37.03 3.30 6 9 -5 7.60 1.34 -6 -9 -5 9.23 1.79 6 9 -4 6.80 1.45 -6 -9 -4 8.35 1.70 6 9 -3 70.54 4.89 -6 -9 -3 65.15 4.75 6 9 -2 38.87 3.78 -6 -9 -2 31.89 3.32 6 9 -1 38.18 3.80 -6 -9 -1 32.62 3.26 6 9 0 13.75 2.33 -6 -9 0 9.59 1.74 6 9 1 35.29 3.76 6 9 2 39.25 3.93 6 9 3 71.39 5.16 -6 9 -3 72.72 3.58 6 9 4 9.04 1.81 -6 9 -4 8.40 1.28 6 9 5 9.72 1.69 -6 9 -5 10.01 1.32 6 9 6 40.89 3.09 -6 9 -6 38.06 2.49 -6 9 -7 4.65 0.85 -6 -10 -5 13.13 1.76 6 10 -4 11.39 1.50 -6 -10 -4 9.68 1.58 6 10 -3 4.47 1.03 -6 -10 -3 3.35 1.01 6 10 -2 13.02 1.90 -6 -10 -2 9.22 1.64 6 10 -1 23.28 2.66 -6 -10 -1 18.05 2.12 6 10 0 2.55 0.98 -6 -10 0 2.49 0.85 6 10 1 20.99 2.59 -6 -10 1 15.07 1.77 6 10 2 12.98 2.04 6 10 3 4.19 1.10 6 10 4 12.01 1.78 6 11 -1 2.88 0.72 6 11 0 44.37 3.04 6 11 1 2.81 0.79 6 11 2 25.18 2.28 7 0 0 0.24 0.65 7 0 -1 -0.21 0.43 7 0 1 -0.24 0.51 7 0 2 4.10 1.22 7 0 -2 4.30 1.20 7 0 -3 -0.22 1.01 7 0 -4 12.35 2.01 7 0 -5 23.33 2.84 7 0 -6 8.81 1.65 7 0 -7 34.79 3.07 7 0 -8 0.09 0.40 -7 0 -8 0.10 0.39 7 0 -9 1.34 0.74 -7 0 -9 0.29 0.32 -7 0 -10 1.73 0.59 -7 -1 -10 23.17 2.09 7 1 -9 7.20 1.09 -7 -1 -9 4.65 1.07 -7 -1 -8 68.14 4.11 7 1 -8 77.52 4.12 7 1 -7 12.88 1.92 -7 -1 -7 8.23 1.53 7 1 -6 7.67 1.58 7 1 -5 -0.07 0.99 7 1 -4 16.43 2.57 7 1 -3 2.16 1.18 7 -1 2 73.19 4.75 7 1 -2 70.47 5.51 7 -1 1 31.69 3.25 7 1 -1 37.05 4.06 7 -1 0 104.04 6.13 7 1 0 103.29 6.65 7 -1 -1 36.08 3.64 7 1 1 36.21 3.89 7 -1 -2 60.53 4.75 7 1 2 63.48 4.93 7 -1 -3 1.12 0.44 7 1 3 3.69 1.25 7 -1 -4 19.93 2.65 7 -1 -5 1.72 0.74 7 -1 -6 7.33 1.43 7 -1 -7 12.90 1.84 7 -1 -8 78.85 4.08 7 -1 -9 10.45 1.39 -7 1 -9 5.84 1.12 -7 1 -10 24.32 1.97 -7 1 -11 23.23 1.94 -7 -2 -10 1.98 0.67 -7 -2 -9 26.41 2.44 7 2 -9 28.14 2.05 7 2 -8 1.88 0.66 -7 -2 -8 1.42 0.75 7 2 -7 2.39 0.73 -7 -2 -7 2.81 0.87 7 2 -6 18.63 2.43 -7 -2 -6 15.73 2.09 7 2 -5 36.70 3.68 7 2 -4 15.25 2.53 7 2 -3 6.57 1.69 7 2 -2 39.06 4.18 7 -2 1 4.93 1.18 7 2 -1 5.37 1.51 7 -2 0 5.90 1.38 7 2 0 11.94 2.46 7 -2 -1 5.70 1.38 7 2 1 3.60 1.32 7 -2 -2 42.50 3.73 7 2 2 38.84 3.97 7 -2 -3 5.82 1.45 7 2 3 7.53 1.74 7 -2 -4 16.13 2.27 7 -2 -5 37.70 3.40 7 -2 -6 20.44 2.34 7 -2 -7 5.65 1.33 7 -2 -8 5.78 1.35 7 -2 -9 38.68 2.45 -7 2 -10 4.51 1.02 -7 -3 -10 24.58 2.06 -7 -3 -9 19.61 2.08 7 3 -9 23.15 1.69 7 3 -8 0.69 0.54 -7 -3 -8 0.15 0.39 -7 -3 -7 23.51 2.54 7 3 -7 26.60 2.64 -7 -3 -6 38.25 3.33 7 3 -6 45.77 3.85 7 3 -5 12.91 2.22 -7 -3 -5 9.97 1.78 7 3 -4 22.33 3.06 7 3 -3 105.75 6.75 7 3 -2 32.21 3.80 7 -3 1 28.96 2.68 7 3 -1 24.21 3.26 7 -3 0 51.84 3.73 7 3 0 50.60 4.74 7 -3 -1 29.25 2.88 7 3 1 27.04 3.47 7 -3 -2 33.70 3.15 7 3 2 31.38 3.63 7 -3 -3 119.89 5.82 7 3 3 107.46 6.42 7 -3 -4 20.16 2.38 7 3 4 20.44 2.59 7 -3 -5 14.10 2.05 7 -3 -6 55.69 3.64 7 -3 -7 32.63 2.66 7 -3 -8 8.76 1.63 -7 3 -9 26.99 2.49 -7 3 -10 31.03 2.24 -7 -4 -9 32.19 2.49 7 4 -8 1.00 0.47 -7 -4 -8 1.61 0.63 7 4 -7 53.08 3.55 -7 -4 -7 46.97 3.51 7 4 -6 45.14 3.68 -7 -4 -6 39.67 3.33 7 4 -5 17.54 2.50 -7 -4 -5 16.23 2.17 7 4 -4 22.32 2.95 7 4 -3 14.01 2.47 7 4 -2 19.62 3.02 7 4 -1 50.94 4.79 7 -4 0 5.91 1.33 7 4 0 6.25 1.65 7 -4 -1 56.97 3.69 7 4 1 51.95 4.74 7 -4 -2 23.50 2.46 7 4 2 15.46 2.56 7 -4 -3 18.78 2.22 7 4 3 12.53 2.17 -7 4 -3 20.08 2.53 7 -4 -4 31.72 2.87 7 4 4 25.18 2.94 7 -4 -5 21.88 2.37 7 -4 -6 58.92 3.58 -7 4 -6 60.75 4.27 -7 4 -7 66.87 4.23 -7 4 -8 0.50 0.36 -7 4 -9 37.85 2.56 -7 4 -10 4.67 0.79 -7 -5 -8 26.28 2.33 7 5 -7 17.68 1.86 -7 -5 -7 16.80 2.00 7 5 -6 35.05 3.05 -7 -5 -6 31.39 2.83 7 5 -5 6.53 1.48 -7 -5 -5 5.01 1.14 7 5 -4 24.23 2.94 -7 -5 -4 24.74 2.59 7 5 -3 4.04 1.21 7 5 -2 1.19 0.69 7 5 -1 30.46 3.64 7 5 0 1.77 0.61 7 -5 -1 40.32 2.93 7 5 1 31.90 3.62 7 -5 -2 7.09 1.55 7 5 2 1.90 0.83 -7 5 -3 4.35 1.08 7 5 3 3.80 1.13 7 5 4 29.95 3.18 -7 5 -4 30.97 2.71 -7 5 -5 8.80 1.45 -7 5 -6 35.25 2.85 -7 5 -7 17.29 1.86 -7 5 -8 33.25 2.38 -7 5 -9 4.75 0.82 7 6 -7 2.36 0.50 -7 -6 -7 3.14 0.84 7 6 -6 7.38 1.30 -7 -6 -6 5.12 1.03 7 6 -5 3.25 1.00 -7 -6 -5 4.47 1.04 7 6 -4 8.57 1.65 -7 -6 -4 6.56 1.31 7 6 -3 8.67 1.74 7 6 -2 1.09 0.63 7 6 -1 86.04 5.75 7 6 0 33.42 3.58 7 6 1 77.15 5.43 7 6 2 1.86 0.85 7 6 3 7.85 1.63 -7 6 -3 7.59 1.16 -7 6 -4 8.33 1.26 7 6 4 7.05 1.38 -7 6 -5 5.35 1.04 -7 6 -6 5.99 1.06 -7 6 -7 2.60 0.66 -7 6 -8 10.16 1.16 7 7 -6 29.74 2.10 -7 -7 -6 27.01 2.17 7 7 -5 15.71 1.83 -7 -7 -5 11.86 1.46 7 7 -4 40.86 3.22 -7 -7 -4 31.54 2.51 7 7 -3 11.56 1.85 -7 -7 -3 9.80 1.38 7 7 -2 41.20 3.66 7 7 -1 16.24 2.38 7 7 0 19.25 2.56 7 7 1 14.97 2.27 7 7 2 35.91 3.41 7 7 3 12.22 1.94 7 7 4 35.80 3.04 -7 7 -4 38.16 2.27 -7 7 -5 14.74 1.42 -7 7 -6 31.31 1.99 7 8 -4 1.92 0.63 7 8 -3 17.20 1.99 7 8 -2 26.96 2.60 7 8 -1 14.04 1.97 7 8 0 304.67 9.23 7 8 1 13.95 1.98 7 8 2 27.93 2.70 7 8 3 16.59 1.99 7 9 -1 41.24 2.83 7 9 0 137.66 5.25 7 9 1 43.76 2.94 8 0 0 -0.59 0.61 8 0 1 5.34 0.99 8 0 -1 3.55 0.83 8 0 -2 11.73 1.60 8 0 -3 71.06 3.92 8 0 -4 45.41 3.02 8 0 -5 16.54 1.74 8 0 -6 2.98 0.73 8 0 -7 14.27 1.31 8 1 -7 5.59 0.83 8 1 -6 8.62 1.16 8 1 -5 -0.32 0.44 8 1 -4 135.86 5.34 8 1 -3 23.14 2.31 8 1 -2 44.52 3.29 8 -1 1 50.89 2.87 8 1 -1 51.03 3.51 8 -1 0 9.15 1.31 8 1 0 9.14 1.40 8 -1 -1 51.69 3.21 8 1 1 49.02 3.23 8 -1 -2 49.47 3.15 8 -1 -3 25.94 2.29 8 -1 -4 144.08 5.14 8 -1 -5 0.78 0.55 8 -1 -6 10.94 1.31 8 -1 -7 9.08 1.06 8 2 -6 8.36 1.10 8 2 -5 1.24 0.39 8 2 -4 81.24 4.11 8 2 -3 2.80 0.77 8 2 -2 47.30 3.41 8 2 -1 38.87 3.12 8 -2 0 3.27 0.83 8 2 0 1.18 0.35 8 -2 -1 43.94 2.74 8 2 1 39.99 2.98 8 -2 -2 49.92 2.96 8 2 2 48.30 3.08 8 -2 -3 5.88 1.14 8 -2 -4 91.14 3.85 -8 2 -4 76.19 3.28 -8 2 -5 1.43 0.54 8 -2 -5 4.82 1.02 8 -2 -6 13.92 1.46 8 3 -6 29.69 1.94 8 3 -5 2.26 0.53 8 3 -4 6.67 1.15 8 3 -3 96.53 4.65 8 3 -2 19.43 2.17 8 3 -1 12.41 1.72 8 3 0 1.99 0.74 8 -3 -1 16.39 1.56 8 3 1 11.51 1.59 8 -3 -2 24.49 1.94 8 3 2 18.22 1.86 8 -3 -3 107.48 3.95 8 -3 -4 14.03 1.54 8 4 -5 3.46 0.67 8 4 -4 42.88 2.76 8 4 -3 32.22 2.57 8 4 -2 12.24 1.66 8 4 -1 26.80 2.46 8 4 0 6.78 1.25 8 4 1 30.43 2.53 8 4 2 15.77 1.67 8 5 -4 11.74 1.28 8 5 -3 5.73 0.98 8 5 -2 34.46 2.56 8 5 -1 9.48 1.42 8 5 0 6.68 1.18 8 5 1 12.20 1.50 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 88977 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, 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 0.4556(2) 0.85422(10) 0.44088(9) 0.0213(3) Uani 1 1 d . . . . . O1 O 0.6243(2) 0.53722(13) 0.21368(10) 0.0147(4) Uani 1 1 d . . . . . O2 O 0.5179(3) 0.64377(13) 0.49728(10) 0.0178(4) Uani 1 1 d . . . . . N1 N 0.5613(3) 0.71533(15) 0.23835(13) 0.0126(4) Uani 1 1 d . . . . . N2 N 0.5705(3) 0.59297(15) 0.35449(13) 0.0119(4) Uani 1 1 d . . . . . C1 C 0.5879(3) 0.61164(17) 0.26498(15) 0.0113(4) Uani 1 1 d . . . . . C2 C 0.5288(3) 0.66852(18) 0.41830(15) 0.0132(5) Uani 1 1 d . . . . . C3 C 0.5002(3) 0.77525(17) 0.38266(15) 0.0141(5) Uani 1 1 d . . . . . C4 C 0.5141(3) 0.79612(18) 0.29611(15) 0.0134(5) Uani 1 1 d . . . . . O3 O 0.5850(3) 0.37977(12) 0.39812(11) 0.0158(4) Uani 1 1 d . . . . . O4 O 0.4124(2) 0.24078(13) 0.44646(11) 0.0169(4) Uani 1 1 d . . . . . N3 N 0.6860(3) 0.44633(15) 0.55662(13) 0.0115(4) Uani 1 1 d . . . . . C5 C 0.5082(3) 0.32529(17) 0.45818(15) 0.0120(4) Uani 1 1 d . . . . . C6 C 0.5342(3) 0.36196(17) 0.55414(15) 0.0111(4) Uani 1 1 d . . . . . C7 C 0.3508(3) 0.4040(2) 0.59708(16) 0.0148(5) Uani 1 1 d . . . . . C8 C 0.3782(3) 0.42732(18) 0.69433(15) 0.0131(5) Uani 1 1 d . . . . . C9 C 0.3883(4) 0.5327(2) 0.72611(16) 0.0166(5) Uani 1 1 d . . . . . C10 C 0.4126(4) 0.5529(2) 0.81579(17) 0.0207(5) Uani 1 1 d . . . . . C11 C 0.4319(3) 0.4681(2) 0.87503(17) 0.0194(5) Uani 1 1 d . . . . . C12 C 0.4265(3) 0.3624(2) 0.84429(16) 0.0173(5) Uani 1 1 d . . . . . C13 C 0.3987(3) 0.34218(18) 0.75456(16) 0.0158(5) Uani 1 1 d . . . . . H1 H 0.565(5) 0.728(2) 0.175(2) 0.036(9) Uiso 1 1 d . . . . . H2 H 0.581(5) 0.524(3) 0.373(2) 0.030(9) Uiso 1 1 d . . . . . H3A H 0.629(5) 0.514(3) 0.534(2) 0.043(10) Uiso 1 1 d . . . . . H3B H 0.745(5) 0.455(2) 0.613(2) 0.027(8) Uiso 1 1 d . . . . . H3C H 0.786(4) 0.423(2) 0.5217(19) 0.023(8) Uiso 1 1 d . . . . . H4 H 0.490(5) 0.864(3) 0.269(2) 0.029(8) Uiso 1 1 d . . . . . H6 H 0.587(4) 0.298(2) 0.5886(18) 0.016(7) Uiso 1 1 d . . . . . H7A H 0.247(4) 0.348(2) 0.5895(17) 0.010(6) Uiso 1 1 d . . . . . H7B H 0.304(4) 0.473(2) 0.5625(19) 0.022(8) Uiso 1 1 d . . . . . H9 H 0.378(4) 0.588(2) 0.6822(19) 0.022(7) Uiso 1 1 d . . . . . H10 H 0.417(5) 0.629(3) 0.838(2) 0.042(10) Uiso 1 1 d . . . . . H11 H 0.451(4) 0.482(2) 0.938(2) 0.025(8) Uiso 1 1 d . . . . . H12 H 0.446(5) 0.300(2) 0.885(2) 0.031(9) Uiso 1 1 d . . . . . H13 H 0.387(4) 0.266(2) 0.7314(19) 0.026(8) 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 0.0362(8) 0.0157(6) 0.0121(7) -0.0045(6) 0.0000(6) 0.0060(6) O1 0.0207(8) 0.0132(7) 0.0101(8) 0.0001(6) 0.0042(6) 0.0001(7) O2 0.0275(9) 0.0190(7) 0.0068(8) 0.0020(7) 0.0000(7) 0.0023(7) N1 0.0166(9) 0.0126(8) 0.0085(9) 0.0023(7) 0.0002(7) 0.0002(7) N2 0.0157(9) 0.0119(9) 0.0081(9) 0.0018(7) 0.0014(7) 0.0014(8) C1 0.0117(10) 0.0135(10) 0.0086(10) 0.0011(8) 0.0009(8) -0.0002(8) C2 0.0136(10) 0.0160(10) 0.0101(11) -0.0004(8) -0.0004(8) -0.0001(9) C3 0.0190(12) 0.0124(10) 0.0111(11) -0.0035(8) -0.0009(9) 0.0012(9) C4 0.0148(11) 0.0137(10) 0.0116(11) -0.0001(9) -0.0014(9) -0.0007(9) O3 0.0248(9) 0.0147(7) 0.0079(8) 0.0001(6) 0.0008(7) -0.0021(7) O4 0.0192(8) 0.0188(8) 0.0126(8) -0.0039(7) 0.0003(7) -0.0069(7) N3 0.0126(8) 0.0145(9) 0.0073(9) 0.0001(8) -0.0012(8) -0.0009(8) C5 0.0126(10) 0.0148(10) 0.0087(10) -0.0023(8) -0.0015(8) 0.0021(9) C6 0.0130(10) 0.0122(9) 0.0080(10) 0.0007(9) -0.0007(9) -0.0006(9) C7 0.0122(11) 0.0215(11) 0.0107(11) -0.0011(10) 0.0000(9) 0.0003(10) C8 0.0097(10) 0.0203(11) 0.0093(11) -0.0007(9) 0.0010(9) 0.0004(8) C9 0.0195(11) 0.0168(11) 0.0136(12) -0.0005(9) 0.0017(10) 0.0015(10) C10 0.0246(12) 0.0211(12) 0.0163(12) -0.0048(10) 0.0027(10) -0.0019(11) C11 0.0168(12) 0.0305(13) 0.0109(12) -0.0031(10) -0.0001(9) -0.0041(11) C12 0.0160(12) 0.0237(12) 0.0121(11) 0.0035(10) 0.0017(9) 0.0003(10) C13 0.0163(11) 0.0173(11) 0.0137(12) 0.0001(9) 0.0016(9) -0.0003(9) 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' 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' F F 0.0727 0.0534 '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 122.36(19) . . ? C1 N1 H1 116.5(18) . . ? C4 N1 H1 120.9(19) . . ? C2 N2 C1 126.39(19) . . ? C2 N2 H2 116(2) . . ? C1 N2 H2 117(2) . . ? O1 C1 N1 123.3(2) . . ? O1 C1 N2 120.74(19) . . ? N1 C1 N2 115.94(19) . . ? O2 C2 N2 121.5(2) . . ? O2 C2 C3 125.5(2) . . ? N2 C2 C3 113.04(19) . . ? C4 C3 F1 120.9(2) . . ? C4 C3 C2 122.2(2) . . ? F1 C3 C2 116.88(19) . . ? C3 C4 N1 120.0(2) . . ? C3 C4 H4 125.6(19) . . ? N1 C4 H4 114.3(19) . . ? C6 N3 H3A 107(2) . . ? C6 N3 H3B 114.2(19) . . ? H3A N3 H3B 113(3) . . ? C6 N3 H3C 107.9(19) . . ? H3A N3 H3C 112(3) . . ? H3B N3 H3C 103(3) . . ? O3 C5 O4 125.2(2) . . ? O3 C5 C6 118.41(19) . . ? O4 C5 C6 116.4(2) . . ? N3 C6 C7 110.41(18) . . ? N3 C6 C5 108.46(17) . . ? C7 C6 C5 113.77(18) . . ? N3 C6 H6 105.9(16) . . ? C7 C6 H6 110.7(17) . . ? C5 C6 H6 107.3(15) . . ? C8 C7 C6 111.80(19) . . ? C8 C7 H7A 109.4(15) . . ? C6 C7 H7A 108.9(15) . . ? C8 C7 H7B 111.6(15) . . ? C6 C7 H7B 109.0(16) . . ? H7A C7 H7B 106(2) . . ? C9 C8 C13 118.4(2) . . ? C9 C8 C7 121.4(2) . . ? C13 C8 C7 120.1(2) . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 123.5(17) . . ? C8 C9 H9 115.6(17) . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119(2) . . ? C9 C10 H10 120(2) . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11 120.8(17) . . ? C12 C11 H11 119.5(17) . . ? C11 C12 C13 119.9(2) . . ? C11 C12 H12 121.1(18) . . ? C13 C12 H12 119.0(18) . . ? C12 C13 C8 120.8(2) . . ? C12 C13 H13 121.1(17) . . ? C8 C13 H13 118.1(17) . . ? 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 1.354(2) . ? O1 C1 1.232(3) . ? O2 C2 1.236(3) . ? N1 C1 1.360(3) . ? N1 C4 1.370(3) . ? N1 H1 0.97(3) . ? N2 C2 1.377(3) . ? N2 C1 1.379(3) . ? N2 H2 0.90(3) . ? C2 C3 1.443(3) . ? C3 C4 1.338(3) . ? C4 H4 0.95(3) . ? O3 C5 1.254(3) . ? O4 C5 1.257(3) . ? N3 C6 1.492(3) . ? N3 H3A 0.99(3) . ? N3 H3B 0.95(3) . ? N3 H3C 0.92(3) . ? C5 C6 1.532(3) . ? C6 C7 1.532(3) . ? C6 H6 1.02(3) . ? C7 C8 1.512(3) . ? C7 H7A 1.01(3) . ? C7 H7B 1.05(3) . ? C8 C9 1.393(3) . ? C8 C13 1.402(3) . ? C9 C10 1.390(3) . ? C9 H9 0.96(3) . ? C10 C11 1.388(4) . ? C10 H10 1.00(3) . ? C11 C12 1.392(4) . ? C11 H11 0.98(3) . ? C12 C13 1.394(3) . ? C12 H12 1.00(3) . ? C13 H13 1.01(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 C4 N1 C1 O1 177.6(2) . . . . ? C4 N1 C1 N2 -2.1(3) . . . . ? C2 N2 C1 O1 -179.4(2) . . . . ? C2 N2 C1 N1 0.2(3) . . . . ? C1 N2 C2 O2 -179.4(2) . . . . ? C1 N2 C2 C3 0.8(3) . . . . ? O2 C2 C3 C4 -179.9(2) . . . . ? N2 C2 C3 C4 -0.1(3) . . . . ? O2 C2 C3 F1 -0.8(4) . . . . ? N2 C2 C3 F1 179.02(19) . . . . ? F1 C3 C4 N1 179.3(2) . . . . ? C2 C3 C4 N1 -1.6(4) . . . . ? C1 N1 C4 C3 2.8(4) . . . . ? O3 C5 C6 N3 -12.0(3) . . . . ? O4 C5 C6 N3 166.98(18) . . . . ? O3 C5 C6 C7 111.3(2) . . . . ? O4 C5 C6 C7 -69.7(3) . . . . ? N3 C6 C7 C8 -64.2(3) . . . . ? C5 C6 C7 C8 173.56(18) . . . . ? C6 C7 C8 C9 106.8(3) . . . . ? C6 C7 C8 C13 -71.6(3) . . . . ? C13 C8 C9 C10 -1.8(4) . . . . ? C7 C8 C9 C10 179.7(2) . . . . ? C8 C9 C10 C11 1.6(4) . . . . ? C9 C10 C11 C12 -0.1(4) . . . . ? C10 C11 C12 C13 -1.0(4) . . . . ? C11 C12 C13 C8 0.8(4) . . . . ? C9 C8 C13 C12 0.7(3) . . . . ? C7 C8 C13 C12 179.2(2) . . . . ?