#------------------------------------------------------------------------------ #$Date: 2018-07-13 01:00:16 +0300 (Fri, 13 Jul 2018) $ #$Revision: 209004 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/19/7121950.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_7121950 loop_ _publ_author_name 'Thomson, Connor J.' 'Zhang, Qingzhi' 'Al-Maharik, Nawaf' 'B\"uhl, Michael' 'Cordes, David B.' 'Slawin, Alexandra M. Z.' 'O’Hagan, David' _publ_section_title ; Fluorinated cyclopropanes: synthesis and chemistry of the aryl \a,\b,\b-trifluorocyclopropane motif ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C8CC04964E _journal_year 2018 _chemical_formula_moiety 'C4 H3 F3 O2' _chemical_formula_sum 'C4 H3 F3 O2' _chemical_formula_weight 140.06 _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2018-06-25 _audit_creation_method 'by CrystalStructure 4.3' _audit_update_record ; 2018-06-25 deposited with the CCDC. 2018-07-12 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 101.626(12) _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 5.165(2) _cell_length_b 11.201(5) _cell_length_c 8.564(4) _cell_measurement_reflns_used 1520 _cell_measurement_temperature 173 _cell_measurement_theta_max 27.40 _cell_measurement_theta_min 3.00 _cell_volume 485.3(4) _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b45' _computing_data_collection 'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b45' _computing_molecular_graphics 'CrystalStructure 4.3' _computing_publication_material 'CrystalStructure 4.3 (Rigaku, 2018)' _computing_structure_refinement 'SHELXL Version 2018/3 (Sheldrick, 2008)' _computing_structure_solution 'SIR2011 (Burla, et al., 2012)' _diffrn_ambient_temperature 173 _diffrn_detector_area_resol_mean 5.814 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 5412 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.387 _diffrn_reflns_theta_min 3.034 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_correction_T_min 0.797 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.917 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 280.00 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Ethyl acetate' _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.23 _refine_diff_density_min -0.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_hydrogen_treatment mixed _refine_ls_number_parameters 85 _refine_ls_number_reflns 885 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0338 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.4784P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.1022 _reflns_Friedel_coverage 0.000 _reflns_number_gt 775 _reflns_number_total 885 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file c8cc04964e2.cif _cod_data_source_block 18 _cod_database_code 7121950 _shelx_res_file ; TITL QZDH13 shelxl.res created by SHELXL-2018/3 at 11:04:38 on 29-Mar-2018 CELL 0.71075 5.16500 11.20100 8.56400 90.000 101.626 90.000 ZERR 4 0.00200 0.00500 0.00400 0.000 0.012 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H F O UNIT 16 12 12 8 L.S. 5 FMAP 2 PLAN 5 BOND $H CONF LIST 4 TEMP -100.0 ACTA SIZE 0.240 0.110 0.050 DFIX 0.9800 0.0100 O5 H5 HTAB EQIV $1 -x+2, -y, -z+1 HTAB O5 O4_$1 HTAB WGHT 0.034200 0.478400 FVAR 1.65794 F1 3 0.239916 0.012494 0.232769 11.00000 0.02584 0.03060 = 0.04218 -0.00395 0.00372 0.00613 F2 3 0.273521 -0.104544 -0.037313 11.00000 0.04152 0.03869 = 0.03012 0.00049 -0.00513 -0.00123 F3 3 0.674316 -0.168343 0.059360 11.00000 0.03268 0.04037 = 0.03778 -0.00714 0.01427 0.00027 O4 4 0.850323 -0.118726 0.400447 11.00000 0.02453 0.03069 = 0.03220 -0.00120 0.00200 0.00135 O5 4 0.696102 0.068292 0.405923 11.00000 0.02859 0.02801 = 0.03289 -0.00588 0.00317 -0.00287 H5 2 0.867525 0.091390 0.464207 11.00000 -1.50000 C1 1 0.432848 -0.072110 0.244773 11.00000 0.02221 0.02371 = 0.03032 -0.00060 0.00628 0.00195 C2 1 0.440947 -0.139759 0.095895 11.00000 0.02670 0.02902 = 0.02536 -0.00208 0.00212 0.00045 C3 1 0.342305 -0.202401 0.220569 11.00000 0.02404 0.02634 = 0.03545 -0.00101 0.00368 -0.00298 AFIX 23 H3A 2 0.456379 -0.264653 0.281264 11.00000 -1.20000 H3B 2 0.150261 -0.218819 0.202892 11.00000 -1.20000 AFIX 0 C4 1 0.679942 -0.041179 0.359992 11.00000 0.02469 0.02715 = 0.01920 0.00068 0.00764 -0.00160 HKLF 4 REM QZDH13 REM wR2 = 0.1022, GooF = S = 1.206, Restrained GooF = 1.208 for all data REM R1 = 0.0338 for 775 Fo > 4sig(Fo) and 0.0392 for all 885 data REM 85 parameters refined using 1 restraints END WGHT 0.0342 0.4784 REM Instructions for potential hydrogen bonds HTAB O5 O4_$1 EQIV $2 x+1/2, -y-1/2, z+1/2 HTAB C3 F2_$2 EQIV $3 x-1, y, z HTAB C3 F3_$3 REM Highest difference peak 0.231, deepest hole -0.313, 1-sigma level 0.053 Q1 1 0.5547 -0.0567 0.3046 11.00000 0.05 0.23 Q2 1 0.3680 -0.1342 0.2593 11.00000 0.05 0.22 Q3 1 0.4929 -0.0809 0.1555 11.00000 0.05 0.22 Q4 1 0.9426 -0.1021 0.4609 11.00000 0.05 0.19 Q5 1 0.8205 -0.0796 0.3321 11.00000 0.05 0.18 ; _shelx_res_checksum 85666 _shelx_hkl_file ; 0 1 0 0.62 2.47 0 0 -1 0.65 3.45 0 -1 1 14.29 3.11 0 -1 -1 13.14 4.50 0 1 -1 14.60 3.34 0 -1 -1 11.32 4.87 0 1 1 14.55 4.90 0 -1 -1 14.04 3.25 0 -2 0 7565.54 150.29 0 -2 0 7062.32 132.45 0 -2 0 6686.69 132.53 0 -2 0 7063.70 140.08 -1 0 0 -0.07 2.15 1 0 0 -0.17 2.42 -1 0 0 0.98 2.67 -1 0 1 3130.13 64.26 1 0 -1 3152.84 64.85 1 0 -1 3025.06 60.50 -1 0 1 2975.97 59.82 -1 0 1 3631.51 75.38 0 -2 1 6164.21 117.58 0 -2 1 5874.39 113.37 0 -2 1 6233.50 114.92 0 -2 -1 6382.16 126.07 0 -2 1 6322.76 117.52 0 2 -1 6229.39 114.59 -1 1 0 4642.46 88.18 -1 -1 0 4620.36 87.41 1 -1 0 4625.60 87.35 1 -1 0 4719.70 89.89 -1 -1 0 4678.48 89.28 1 1 0 4776.89 91.62 -1 1 0 4708.20 92.17 1 -1 0 4691.62 91.94 1 1 0 4616.50 88.03 -1 1 1 2699.49 57.72 1 -1 -1 3301.88 69.53 1 1 -1 2820.82 58.89 -1 -1 1 2825.97 58.55 -1 -1 1 2700.29 56.11 1 -1 -1 2769.39 56.71 -1 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4 -3 5 9.86 5.90 4 -3 5 5.63 5.54 -4 3 -5 7.35 4.87 -3 0 9 15.51 6.05 4 -9 -1 582.58 20.42 4 9 -1 587.93 16.76 -4 -9 1 594.79 17.06 5 0 3 378.93 13.52 5 0 3 427.84 14.76 -5 0 -3 434.29 13.67 3 0 7 240.69 11.38 3 0 7 269.05 12.30 -5 6 3 44.50 6.53 -5 -6 3 44.68 6.44 5 6 -3 46.18 7.00 5 -6 -3 48.73 6.81 2 -2 8 5.08 5.30 2 2 8 7.49 4.77 2 -2 8 5.88 4.67 2 2 8 7.01 5.88 -4 9 2 72.32 7.67 4 -9 -2 74.39 9.06 4 9 -2 65.95 7.49 -4 -9 2 62.15 6.85 2 9 5 24.69 5.73 2 -9 5 22.81 6.28 2 -9 5 20.60 6.04 1 -9 6 132.53 9.65 1 -9 6 167.66 10.41 3 -1 -9 -0.71 6.01 -3 -1 9 5.61 5.64 3 1 -9 4.74 5.80 -3 1 9 3.87 5.63 4 5 -7 -0.21 5.48 -4 -5 7 1.84 4.61 -4 -5 7 2.25 5.18 4 -5 -7 4.34 5.46 -4 5 7 5.80 4.40 -5 1 -3 95.41 8.00 5 -1 3 95.99 8.31 5 1 3 102.23 8.88 5 1 3 86.26 7.71 -5 -1 -3 104.71 7.92 5 -1 3 95.87 8.26 3 1 7 1.73 5.73 3 -1 7 -0.40 4.71 3 1 7 3.39 4.68 3 -1 7 7.49 5.92 5 -4 2 53.62 7.14 5 -4 2 62.70 7.40 -5 -4 -2 55.86 6.55 -5 4 -2 52.75 6.59 2 10 4 325.45 13.44 2 -10 4 324.50 15.32 2 -10 4 313.49 14.36 -4 -7 -3 69.43 6.68 4 7 3 55.10 7.10 4 -7 3 60.10 7.61 -4 7 -3 62.80 6.75 3 10 -4 13.62 4.72 3 -10 -4 12.26 6.23 -3 10 4 10.29 5.04 3 -10 2 80.80 8.27 -3 -10 -2 94.30 7.78 3 10 2 83.76 7.73 -3 10 -2 86.45 7.96 1 -12 2 147.03 9.44 1 -12 2 144.85 10.96 -1 -12 -2 146.89 9.33 -4 -2 8 25.86 6.35 4 2 -8 32.50 6.63 4 -2 -8 34.06 6.71 -4 -2 8 30.44 5.46 -4 2 8 27.02 7.09 -4 2 8 26.09 5.09 1 7 -8 58.87 7.01 1 -7 -8 54.47 7.79 -1 7 8 50.80 6.86 -1 -7 8 60.24 6.40 -1 -7 8 52.70 6.48 -5 6 0 359.86 13.45 5 -6 0 367.90 15.28 -5 -6 0 347.41 12.77 5 6 0 337.22 13.45 -2 -4 9 165.95 10.05 -2 4 9 175.72 11.46 -2 -4 9 142.36 8.51 2 -4 -9 153.47 10.49 2 4 -9 151.21 9.76 4 8 2 52.75 6.66 -4 8 -2 53.80 7.17 -4 -8 -2 56.40 6.52 1 -11 4 19.30 6.51 1 -11 4 15.91 6.33 -4 -9 0 124.50 8.63 4 -9 0 133.66 10.40 -4 9 0 132.31 9.06 4 9 0 123.10 8.73 2 -11 -4 116.48 9.50 2 -11 -4 136.82 9.89 -2 6 -7 116.13 8.72 2 -6 7 103.48 8.31 2 6 7 99.66 8.88 5 -3 -6 3.61 5.35 5 -3 -6 -1.75 6.53 5 3 -6 -0.29 5.20 -5 3 6 -1.15 4.45 -5 -3 6 -0.84 4.83 -5 -3 6 -0.56 5.69 0 -12 3 84.67 7.90 0 -12 -3 89.29 8.24 -1 0 -9 28.86 7.12 1 0 9 23.81 5.86 3 2 -9 1.00 5.37 -3 -2 9 2.15 3.84 3 -2 -9 -0.56 5.82 -3 -2 9 3.09 5.49 0 4 -9 200.86 11.05 0 -4 -9 185.13 11.87 0 4 9 187.01 10.76 5 -2 3 99.15 8.44 5 -2 3 102.81 8.70 -5 -2 -3 115.73 8.09 5 2 3 109.79 9.05 -5 2 -3 108.62 8.22 3 2 7 1.25 5.73 3 -2 7 1.79 4.54 3 -2 7 1.46 5.58 3 2 7 3.30 4.33 -1 -1 -9 61.50 8.28 1 1 9 47.88 6.57 1 -1 9 51.39 6.69 -1 1 -9 55.78 8.06 4 -9 -3 173.78 11.63 4 9 -3 204.78 10.33 -4 9 3 193.48 10.10 -4 -9 3 200.41 10.34 -1 -12 3 32.96 6.45 1 -12 -3 30.85 6.76 2 -3 8 25.37 5.85 2 3 8 24.48 5.64 2 3 8 25.68 6.73 -1 -10 6 28.85 6.17 -1 -10 6 27.13 5.74 4 -6 4 166.30 10.55 4 6 4 174.99 10.38 -4 6 -4 182.99 10.18 2 -8 6 2.05 5.85 2 -8 6 3.26 5.91 2 8 6 4.50 5.37 5 5 -5 127.20 9.46 -5 5 5 118.02 8.55 -5 -5 5 114.53 8.06 5 -5 -5 117.15 8.68 4 4 5 6.75 5.49 4 -4 5 7.70 5.55 4 -4 5 6.22 6.06 -4 4 -5 10.10 5.30 2 -12 -1 2.96 6.16 2 -12 -1 2.37 5.59 -2 -12 1 0.32 5.08 4 -7 -6 -1.99 4.63 -4 -7 6 -0.31 4.83 4 -7 -6 -3.30 5.96 -4 7 6 2.92 4.97 4 7 -6 -1.04 5.30 0 -7 8 -1.84 4.19 0 7 -8 0.97 5.22 0 7 8 5.12 5.54 0 -7 -8 -0.23 6.56 0 -7 8 -2.80 4.91 -4 -8 5 7.87 5.08 4 -8 -5 7.52 6.04 4 8 -5 8.89 5.31 -4 8 5 8.35 5.29 -5 6 4 25.56 5.77 5 -6 -4 26.33 5.94 5 6 -4 25.75 6.22 -3 11 1 158.09 9.52 3 11 -1 161.00 9.47 -3 -11 1 179.72 9.50 3 -11 -1 174.87 11.08 -4 3 8 2.18 4.21 4 3 -8 -0.02 5.77 -4 -3 8 -6.59 5.02 -4 3 8 -1.28 5.77 4 -3 -8 1.03 5.50 -4 -3 8 -0.58 4.19 1 -5 -9 -1.18 6.65 1 5 -9 1.39 5.91 -1 5 9 -2.88 5.78 -1 -5 9 -0.51 5.15 2 -12 0 -0.29 6.45 2 -12 0 5.16 5.72 -2 -12 0 3.98 4.94 -2 -7 8 4.19 4.52 -2 7 8 0.30 5.53 2 7 -8 -1.92 4.80 -2 -7 8 -0.33 5.12 2 -7 -8 2.70 6.15 2 -11 3 43.72 7.31 2 11 3 41.06 6.31 2 -11 3 39.44 7.56 -2 -11 -3 46.68 6.27 -1 2 -9 0.04 5.84 1 2 9 -2.32 5.16 0 -10 6 3.93 5.62 0 -10 6 5.07 5.13 -1 -11 5 249.07 11.66 -1 -11 5 243.17 11.04 -1 -6 -8 13.05 6.75 1 6 8 11.29 5.05 -1 6 -8 15.05 5.84 1 -6 8 9.71 4.92 1 -8 7 22.60 6.05 1 -8 7 20.35 5.99 -1 -8 -7 22.50 6.68 -1 -9 7 56.04 6.95 -1 -9 7 49.45 6.74 1 -9 -7 47.00 7.60 3 11 -2 28.91 5.44 -3 -11 2 31.74 5.79 -3 11 2 31.47 6.15 3 -11 -2 30.70 7.17 3 11 0 10.09 5.12 3 -11 0 10.61 5.84 -3 -11 0 13.89 5.22 3 -3 -9 -6.02 5.82 3 3 -9 -2.69 5.64 -3 -3 9 2.09 5.62 -3 -3 9 -0.14 3.88 -5 -3 -3 100.02 7.83 5 -3 3 79.08 8.04 -5 3 -3 94.48 7.64 5 3 3 95.78 8.66 5 -3 3 87.13 8.38 3 3 7 6.41 4.51 3 -3 7 8.82 5.61 3 -3 7 10.88 5.52 3 3 7 6.22 5.47 0 -11 5 17.85 6.43 0 -11 5 15.49 5.58 3 -6 -8 140.33 9.96 -3 -6 8 138.86 8.67 -3 -6 8 134.71 9.17 3 6 -8 145.01 9.31 -3 6 8 143.72 10.12 3 6 6 206.56 11.12 3 -6 6 189.32 11.63 2 -12 -2 -0.39 6.15 -2 -12 2 -3.10 5.07 2 -12 -2 -0.37 5.44 -4 -9 -1 0.61 4.74 4 -9 1 0.38 5.89 4 9 1 0.05 5.27 -4 9 -1 -0.82 5.41 5 6 1 90.02 8.29 5 -6 1 79.15 8.74 -5 6 -1 76.93 7.34 -5 -6 -1 80.52 7.37 5 -5 2 7.73 6.04 -5 -5 -2 9.61 5.11 -5 5 -2 11.96 5.48 -5 -7 2 59.97 6.82 5 7 -2 55.53 7.05 -5 7 2 62.12 7.16 5 -4 -6 10.44 5.97 -5 -4 6 17.13 6.61 -5 -4 6 13.48 5.23 -5 4 6 14.75 5.46 5 4 -6 18.04 6.66 5 7 -1 69.00 7.59 -5 -7 1 71.21 7.11 5 -7 -1 67.88 8.68 -2 5 9 161.55 11.88 2 -5 -9 124.13 10.08 2 5 -9 106.35 8.27 -2 -5 9 123.23 8.89 -2 -5 9 117.94 7.83 2 -12 1 2.36 5.88 2 -12 1 4.37 5.23 -2 -12 -1 3.98 5.19 3 9 -6 61.28 6.81 3 -9 -6 50.15 8.05 -3 -9 6 61.04 6.84 -3 9 6 56.36 6.63 3 -9 4 15.08 6.22 3 9 4 12.62 5.96 -3 9 -4 10.87 5.98 -5 0 7 139.63 9.74 5 0 -7 142.33 9.65 -5 0 7 148.63 8.99 0 -9 7 11.09 5.46 0 -9 7 7.39 5.25 0 -9 -7 10.25 6.13 -4 6 7 -0.41 4.53 -4 -6 7 -1.74 5.05 4 -6 -7 -0.80 6.56 4 -6 -7 1.49 5.63 4 6 -7 1.10 5.78 1 -12 3 0.69 5.75 -1 -12 -3 0.93 4.83 -2 4 -8 57.58 7.81 2 4 8 44.75 7.50 2 -4 8 49.33 6.71 2 4 8 56.64 6.80 -4 9 4 53.15 7.05 4 -9 -4 57.13 7.94 4 9 -4 60.42 6.74 0 -13 0 -1.83 5.79 1 -3 9 187.70 10.61 -1 -3 -9 208.54 12.39 -1 3 -9 220.42 11.67 1 3 9 191.99 10.82 -5 1 7 9.70 5.20 5 -1 -7 8.71 6.50 -5 -1 7 9.34 4.86 -5 1 7 7.26 6.23 -5 -1 7 8.48 6.28 -6 0 2 -2.20 5.15 6 0 -2 -0.67 5.29 6 0 -2 6.65 5.36 0 5 9 198.54 11.08 0 5 -9 206.99 11.08 0 -5 -9 174.35 11.56 0 -5 9 191.01 11.12 -2 -10 6 1.18 4.95 2 -10 -6 1.65 6.06 -2 -10 6 4.85 4.70 5 7 -3 92.15 8.14 -5 7 3 79.84 7.64 -5 -7 3 84.13 7.57 6 -1 -2 4.41 5.68 6 1 -2 5.77 5.98 6 1 -2 3.47 5.49 6 -1 -2 6.82 6.02 -6 -1 2 7.11 5.13 -6 1 2 4.01 5.20 -4 4 8 8.58 4.81 -4 -4 8 10.17 4.95 -4 4 8 4.06 6.11 -4 -4 8 9.10 5.23 4 -4 -8 4.11 6.05 4 4 -8 3.42 5.97 -3 11 3 32.72 6.43 -3 -11 3 40.12 6.21 3 -11 -3 39.46 7.36 -3 8 7 313.17 11.98 3 -8 -7 340.09 13.04 3 8 -7 342.69 13.14 3 -8 -7 320.97 14.46 -3 -8 7 331.81 12.37 -3 -8 7 329.02 12.55 -3 -11 -1 -0.59 4.92 3 11 1 -0.20 4.89 -3 11 -1 4.71 5.82 3 -11 1 1.15 6.07 3 8 5 33.34 6.93 -3 8 -5 28.15 6.50 0 -13 1 8.25 5.78 0 -13 -1 10.94 5.97 -3 -10 5 20.84 5.86 3 -10 -5 15.16 6.38 -3 10 5 13.18 5.37 3 10 3 69.96 7.76 3 -10 3 72.79 8.28 -3 10 -3 74.68 8.04 6 0 -3 4.28 6.35 6 0 -3 2.79 6.20 6 0 -1 -0.52 5.52 -6 0 1 -0.40 5.33 4 0 6 118.72 8.21 4 0 6 138.57 9.68 1 0 -10 -5.03 6.73 -1 0 10 3.63 5.76 2 -9 -7 12.64 6.77 2 -9 -7 6.24 6.37 -2 -9 7 13.88 5.15 -2 -9 7 12.71 4.93 -5 -7 0 61.54 6.72 -5 7 0 55.30 6.95 5 7 0 69.90 7.66 5 -7 0 66.86 8.55 -4 5 -5 24.06 6.05 4 -5 5 20.41 6.94 6 1 -3 260.72 12.49 6 -1 -3 270.55 12.20 6 1 -3 267.57 12.36 6 -1 -3 265.23 13.02 6 -1 -1 16.00 6.14 -6 -1 1 16.26 5.68 6 1 -1 20.39 6.64 6 -1 -1 19.77 5.97 6 1 -1 20.83 6.00 -6 1 1 19.68 5.97 -5 -2 7 164.44 9.08 -5 -2 7 162.94 10.15 -5 2 7 168.79 10.42 5 -2 -7 168.02 10.41 -5 2 7 173.75 9.50 4 1 6 90.03 8.77 4 1 6 75.25 6.80 4 -1 6 84.12 7.77 4 -1 6 89.64 8.90 -1 -1 10 91.43 8.83 1 1 -10 81.87 8.81 -1 1 10 90.28 8.44 3 4 -9 -2.65 4.88 3 -4 -9 -0.12 5.99 -3 -4 9 -0.42 4.39 -3 4 9 -0.98 6.24 -3 -4 9 -0.37 5.69 -5 4 -3 245.42 10.97 -5 -4 -3 263.92 11.11 5 4 3 230.57 11.54 5 -4 3 237.78 11.44 5 -4 3 221.87 11.30 2 -12 -3 27.63 6.64 2 -12 -3 30.06 6.59 -2 -12 3 33.61 6.31 3 -4 7 5.77 5.54 3 -4 7 6.94 5.83 3 4 7 3.04 6.00 0 -12 4 150.38 9.69 0 -12 4 164.56 10.46 2 -7 7 4.41 5.48 2 7 7 -2.85 5.53 1 -12 -4 -0.84 5.15 -1 -12 4 -2.10 5.32 4 8 3 7.44 5.92 -4 8 -3 9.44 5.63 2 -11 -5 92.43 8.73 -2 -11 5 106.14 8.42 -6 2 2 23.93 5.83 -6 -2 2 21.33 5.86 6 2 -2 17.66 6.02 6 -2 -2 21.17 6.22 6 -2 -2 21.35 6.93 6 2 -2 19.93 5.96 -5 6 5 194.03 10.05 5 6 -5 183.31 10.39 5 -6 -5 176.09 9.91 -5 -6 5 192.79 9.76 1 8 -8 -0.42 4.72 -1 -8 8 -0.97 4.98 -1 8 8 -1.64 4.85 1 -8 -8 -0.05 6.59 -1 -8 8 1.92 4.64 1 -13 0 51.82 8.01 -1 -13 0 54.18 7.14 2 0 -10 3.41 6.68 -1 -13 1 33.68 6.26 1 -13 -1 39.20 7.65 1 6 -9 5.92 5.69 1 -6 -9 9.24 6.93 -1 -6 9 5.17 5.54 -1 6 9 8.94 6.95 5 0 4 5.81 6.57 5 0 4 4.26 5.42 -5 0 -4 -1.57 5.11 4 -7 4 93.15 9.19 -4 7 -4 99.05 8.41 4 7 4 88.20 9.01 6 -2 -3 56.46 8.29 6 2 -3 53.00 7.31 6 2 -3 61.91 8.00 6 -2 -3 61.57 7.61 -2 1 10 180.67 10.79 2 1 -10 179.39 10.75 6 -2 -1 115.43 9.56 -6 -2 1 107.02 8.04 6 2 -1 113.11 9.16 6 -2 -1 103.58 9.08 -6 2 1 111.23 8.41 4 -2 6 5.64 5.61 4 2 6 3.88 6.32 4 -2 6 3.91 6.16 1 2 -10 0.12 6.30 -1 2 10 1.48 5.55 4 -10 -1 210.62 12.65 4 10 -1 239.03 11.02 -4 -10 1 228.22 11.10 2 -12 2 49.94 7.20 -2 -12 -2 50.69 6.63 -5 1 -4 213.04 10.23 5 -1 4 203.82 10.71 5 -1 4 207.04 11.06 5 1 4 209.96 11.70 -5 -5 6 3.36 5.36 -5 5 6 6.33 5.00 5 -5 -6 8.98 5.54 5 5 -6 5.32 5.90 -4 10 2 7.83 5.83 4 10 -2 2.34 5.10 -4 -10 2 0.35 5.28 4 -10 -2 4.82 6.60 -1 -4 -9 -2.43 7.27 1 4 9 2.61 5.27 -1 4 -9 1.25 6.08 -4 9 -2 -0.88 5.13 4 -9 2 0.88 6.35 -4 -9 -2 1.96 4.95 4 9 2 -1.52 5.42 2 10 5 64.35 7.32 2 -10 5 54.01 7.45 2 -10 5 60.33 8.18 0 -13 -2 41.17 7.20 0 -13 2 43.30 7.54 1 -10 6 133.28 9.59 -1 -10 -6 133.91 9.93 1 -10 6 137.19 9.55 5 -7 -4 36.78 7.84 -5 7 4 44.07 6.97 5 7 -4 43.80 7.14 -6 0 4 396.79 13.40 6 0 -4 366.79 14.53 6 0 -4 366.46 14.58 1 -11 5 6.93 6.01 1 -11 5 7.01 5.83 6 0 0 47.42 7.62 -6 0 0 40.53 6.55 6 0 0 45.31 6.90 1 -13 1 11.68 6.91 1 -13 1 10.23 5.50 -1 -13 -1 13.51 5.84 -5 -3 7 -2.54 4.60 -5 3 7 -0.14 4.90 5 -3 -7 -5.06 6.65 -5 -3 7 -3.46 6.80 5 -3 -7 -2.18 6.01 5 3 -7 -2.23 6.20 -6 1 4 4.51 5.64 6 -1 -4 10.08 6.52 6 -1 -4 3.18 6.50 -6 -1 4 9.81 6.08 6 1 -4 8.13 6.92 6 1 -4 6.83 6.60 6 -1 0 1.98 5.99 -6 1 0 4.65 5.73 -6 -1 0 4.88 5.34 1 -7 8 31.24 6.02 1 -7 8 32.47 6.21 -1 -7 -8 37.27 7.47 -5 -6 -2 1.87 5.02 -5 6 -2 6.03 5.51 5 6 2 2.25 5.81 5 -6 2 5.30 6.17 -2 5 -8 170.66 10.48 2 -5 8 162.16 10.16 4 -8 -6 12.48 6.95 -4 8 6 17.49 5.68 -4 -8 6 17.73 5.67 4 8 -6 18.17 5.83 2 -2 -10 12.79 7.44 -2 2 10 16.30 6.52 2 2 -10 8.84 7.10 -2 -2 10 10.23 6.58 0 8 8 2.12 4.81 0 -8 8 -0.40 4.61 0 -8 -8 2.16 6.31 0 -8 8 2.87 5.28 0 0 10 39.78 7.24 0 0 -10 35.60 7.84 6 -3 -2 32.39 7.04 6 -3 -2 35.09 6.57 -6 -3 2 25.54 5.56 -6 3 2 33.20 6.35 -4 10 0 10.77 6.20 -4 -10 0 13.22 5.61 4 10 0 11.37 5.24 4 -10 0 9.80 6.80 2 6 -9 8.27 5.48 2 -6 -9 4.86 6.37 -2 -6 9 4.29 5.42 -2 -6 9 6.48 4.53 -2 6 9 8.96 6.33 3 -7 -8 62.04 8.07 3 7 -8 69.27 7.70 -3 -7 8 64.60 7.63 -3 -7 8 64.76 7.08 -1 -13 2 17.15 6.20 1 -13 -2 9.03 6.24 2 8 -8 198.72 10.28 -2 -8 8 204.92 10.63 -2 -8 8 179.07 9.42 2 -8 -8 199.82 11.58 2 -11 4 55.12 8.15 2 11 4 52.32 6.83 2 -11 4 51.95 7.84 3 7 6 375.61 14.86 3 -7 6 374.40 16.08 5 -2 4 86.66 8.48 -5 2 -4 83.42 7.51 5 -2 4 85.33 8.27 5 2 4 89.22 8.82 2 -9 6 13.55 6.43 2 -9 6 12.86 6.32 2 9 6 11.06 5.96 -5 7 -1 44.79 7.06 5 7 1 41.71 7.19 5 -7 1 44.25 7.52 -5 -7 -1 46.16 6.51 0 1 10 18.97 6.07 0 -1 -10 17.64 7.32 0 -1 10 19.20 6.18 0 1 -10 23.58 7.46 3 -11 -4 7.34 6.02 -3 11 4 1.05 4.79 -3 11 -2 88.15 8.25 3 11 2 85.93 7.88 -3 -11 -2 92.53 7.67 3 -11 2 84.89 8.79 -4 -5 8 359.63 12.67 4 5 -8 345.28 13.51 4 -5 -8 357.38 13.31 -4 -5 8 327.35 12.74 -4 0 9 0.36 7.04 6 -3 -3 8.77 6.79 6 -3 -3 10.89 5.93 -6 -3 3 13.11 5.84 -6 3 3 10.18 5.70 -6 3 1 1.10 5.37 6 3 -1 1.32 5.49 6 -3 -1 -4.41 5.96 -6 -3 1 2.90 5.10 6 -3 -1 -3.58 5.47 -4 -9 5 -0.24 4.84 -4 9 5 0.21 5.23 4 9 -5 -0.27 5.01 4 -9 -5 -3.60 6.15 4 10 -3 3.24 5.21 -4 -10 3 5.80 5.39 4 -10 -3 3.37 6.36 -4 10 3 6.15 5.77 4 -3 6 88.20 8.29 4 -3 6 78.81 8.14 4 3 6 85.36 8.63 1 3 -10 15.66 6.86 1 -3 -10 18.61 7.39 -1 3 10 14.74 6.40 -6 2 4 356.44 12.90 -6 -2 4 335.23 12.86 6 2 -4 364.40 14.55 6 -2 -4 361.28 13.87 6 2 -4 349.66 14.54 6 -2 -4 347.06 14.77 0 6 9 447.44 18.01 0 6 -9 379.00 13.99 0 -6 -9 376.72 15.16 0 -6 9 368.37 14.35 -6 2 0 126.79 8.60 -6 -2 0 127.76 8.42 6 -2 0 133.32 9.43 6 -2 0 111.84 8.67 6 2 0 129.48 9.61 -4 -1 9 2.73 5.51 -4 1 9 7.72 9.38 4 -1 -9 5.68 6.08 3 -5 -9 11.61 6.58 -3 -5 9 6.58 5.49 -3 5 9 4.67 6.22 -3 -5 9 10.60 5.23 3 5 -9 8.97 5.53 4 7 -7 182.89 10.37 4 -7 -7 193.34 10.36 4 -7 -7 180.06 12.09 -4 7 7 196.33 9.85 -4 -7 7 180.95 9.48 -5 -5 -3 5.97 5.35 -5 5 -3 10.02 5.80 5 -5 3 10.15 6.48 3 -5 7 43.88 7.19 1 -9 7 23.30 5.94 1 -9 7 25.04 6.67 -1 -9 -7 28.27 7.35 -5 -8 2 -1.14 5.18 5 8 -2 1.64 5.17 -5 8 2 -0.80 5.62 1 -12 4 86.56 8.18 1 -12 4 82.93 8.84 0 2 -10 37.51 7.49 0 -2 10 44.27 7.41 0 2 10 49.55 7.63 -5 -8 1 13.91 5.58 5 8 -1 11.08 6.11 2 -12 -4 15.34 6.02 2 -12 -4 18.12 5.97 ; _shelx_hkl_checksum 33557 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 -1/2+X,-1/2-Y,-1/2+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 F1 F 0.2399(3) 0.01249(13) 0.23277(18) 0.0333(4) Uani 1 1 d . . F2 F 0.2735(3) -0.10454(14) -0.03731(17) 0.0385(4) Uani 1 1 d . . F3 F 0.6743(3) -0.16834(14) 0.05936(17) 0.0359(4) Uani 1 1 d . . O4 O 0.8503(3) -0.11873(15) 0.4004(2) 0.0297(4) Uani 1 1 d . . O5 O 0.6961(3) 0.06829(15) 0.4059(2) 0.0303(4) Uani 1 1 d D . H5 H 0.868(3) 0.091(3) 0.464(3) 0.045 Uiso 1 1 d D U C1 C 0.4328(4) -0.0721(2) 0.2448(3) 0.0253(5) Uani 1 1 d . . C2 C 0.4409(4) -0.1398(2) 0.0959(3) 0.0275(5) Uani 1 1 d . . C3 C 0.3423(5) -0.2024(2) 0.2206(3) 0.0289(5) Uani 1 1 d . . H3A H 0.456379 -0.264653 0.281264 0.035 Uiso 1 1 calc R U H3B H 0.150261 -0.218819 0.202892 0.035 Uiso 1 1 calc R U C4 C 0.6799(4) -0.0412(2) 0.3600(3) 0.0232(5) 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 F1 0.0258(7) 0.0306(8) 0.0422(9) -0.0040(6) 0.0037(6) 0.0061(6) F2 0.0415(8) 0.0387(9) 0.0301(8) 0.0005(6) -0.0051(6) -0.0012(7) F3 0.0327(8) 0.0404(9) 0.0378(8) -0.0071(6) 0.0143(6) 0.0003(6) O4 0.0245(8) 0.0307(9) 0.0322(9) -0.0012(7) 0.0020(7) 0.0013(7) O5 0.0286(9) 0.0280(9) 0.0329(9) -0.0059(7) 0.0032(7) -0.0029(7) C1 0.0222(11) 0.0237(12) 0.0303(12) -0.0006(10) 0.0063(9) 0.0020(9) C2 0.0267(11) 0.0290(12) 0.0254(12) -0.0021(10) 0.0021(9) 0.0004(10) C3 0.0240(11) 0.0263(13) 0.0354(13) -0.0010(10) 0.0037(10) -0.0030(10) C4 0.0247(11) 0.0271(12) 0.0192(10) 0.0007(9) 0.0076(9) -0.0016(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (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 C4 O5 H5 114.4(19) F1 C1 C4 113.83(19) F1 C1 C2 115.76(19) C4 C1 C2 121.14(19) F1 C1 C3 116.92(18) C4 C1 C3 120.56(19) C2 C1 C3 57.40(15) F3 C2 F2 109.04(19) F3 C2 C3 121.3(2) F2 C2 C3 120.3(2) F3 C2 C1 120.09(19) F2 C2 C1 116.9(2) C3 C2 C1 62.78(16) C2 C3 C1 59.82(16) C2 C3 H3A 117.8 C1 C3 H3A 117.8 C2 C3 H3B 117.8 C1 C3 H3B 117.8 H3A C3 H3B 114.9 O4 C4 O5 125.9(2) O4 C4 C1 119.3(2) O5 C4 C1 114.78(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C1 1.364(3) F2 C2 1.344(3) F3 C2 1.344(3) O4 C4 1.235(3) O5 C4 1.285(3) O5 H5 0.960(10) C1 C4 1.488(3) C1 C2 1.491(3) C1 C3 1.534(3) C2 C3 1.453(3) C3 H3A 0.9900 C3 H3B 0.9900 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 _geom_hbond_publ_flag O5 H5 O4 0.960(10) 1.697(12) 2.644(2) 168(3) 3_756 yes 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 F1 C1 C2 F3 141.1(2) C4 C1 C2 F3 -3.6(3) C3 C1 C2 F3 -112.2(2) F1 C1 C2 F2 5.3(3) C4 C1 C2 F2 -139.4(2) C3 C1 C2 F2 112.0(2) F1 C1 C2 C3 -106.7(2) C4 C1 C2 C3 108.6(2) F3 C2 C3 C1 110.3(2) F2 C2 C3 C1 -106.8(2) F1 C1 C3 C2 104.7(2) C4 C1 C3 C2 -109.6(2) F1 C1 C4 O4 168.00(19) C2 C1 C4 O4 -46.7(3) C3 C1 C4 O4 21.3(3) F1 C1 C4 O5 -13.4(3) C2 C1 C4 O5 131.9(2) C3 C1 C4 O5 -160.1(2)