# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 loop_ _publ_author_name _publ_author_address 'Andrzej Katrusiak' ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; 'Jeanne Crassous' ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; 'Roman Gajda' '' _publ_contact_author_name 'Andrzej Katrusiak' _publ_contact_author_email KATRAN@AMU.EDU.PL _publ_section_title ; Pressure-controlled aggregation in carboxylic-acids ; _publ_contact_author_address ; Andrzej Katrusiak Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; _publ_contact_author_fax +48(61)8291505 _publ_contact_author_phone +48(61)8291443 # Attachment 'brclf_acid.cif' data_bromochlorofluorocarboxylic_acid_1 _database_code_depnum_ccdc_archive 'CCDC 723999' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromochlorofluorocarboxylic acid ; _chemical_name_common 'bromochlorofluorocarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C2 H Br Cl F O2' _chemical_formula_sum 'C2 H Br Cl F O2' _chemical_formula_weight 191.39 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 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bcn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.458(5) _cell_length_b 6.0708(4) _cell_length_c 21.0950(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2107.7(6) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3367 _cell_measurement_theta_min 3.58 _cell_measurement_theta_max 25.00 _exptl_crystal_description disc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.085 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 8.212 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.33 _exptl_absorpt_correction_T_max 0.488 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; High-pressure measurement at 0.28 GPa. ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 280000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6686 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 481 _reflns_number_gt 413 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed 2.0' _computing_publication_material 'X-seed 2.0' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0861P)^2^+12.5069P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 481 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1611 _refine_ls_goodness_of_fit_ref 1.204 _refine_ls_restrained_S_all 1.204 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.157(4) -1.039(2) 0.7428(7) 0.034(4) Uiso 1 1 d . . . C2 C 1.093(4) -0.961(3) 0.6850(7) 0.09(6) Uani 1 1 d . . . O1 O 1.214(2) -0.9284(19) 0.7598(5) 0.058(3) Uiso 1 1 d . . . H1 H 1.2372 -0.9903 0.7893 0.086 Uiso 1 1 calc R . . O2 O 1.120(3) -1.1946(19) 0.7712(5) 0.060(4) Uiso 1 1 d . . . Br1 Br 1.1778(8) -1.0102(5) 0.61676(11) 0.094(11) Uani 0.43 1 d P . . Br2 Br 1.0851(6) -0.6657(5) 0.68829(13) 0.083(11) Uani 0.57 1 d P . . Cl1 Cl 1.1778(8) -1.0102(5) 0.61676(11) 0.094(11) Uani 0.57 1 d P . . Cl2 Cl 1.0851(6) -0.6657(5) 0.68829(13) 0.083(11) Uani 0.43 1 d P . . F1 F 1.053(3) -1.084(3) 0.6676(7) 0.107(6) Uiso 1 1 d . . . C3 C 1.330(4) -1.046(3) 0.8938(8) 0.039(6) Uiso 1 1 d . . . C4 C 1.354(4) -1.158(3) 0.9599(8) 0.08(6) Uani 1 1 d . . . O3 O 1.398(3) -0.912(2) 0.8818(6) 0.063(4) Uiso 1 1 d . . . H3 H 1.3908 -0.8437 0.8487 0.094 Uiso 1 1 calc R . . O4 O 1.276(3) -1.0773(18) 0.8651(5) 0.10(4) Uani 1 1 d . . . Br3 Br 1.4207(5) -1.3935(3) 0.94379(11) 0.074(9) Uani 0.66 1 d P . . Br4 Br 1.3895(8) -0.9826(5) 1.02085(12) 0.068(11) Uani 0.34 1 d P . . Cl3 Cl 1.4207(5) -1.3935(3) 0.94379(11) 0.074(9) Uani 0.34 1 d P . . Cl4 Cl 1.3895(8) -0.9826(5) 1.02085(12) 0.068(11) Uani 0.66 1 d P . . F2 F 1.281(3) -1.2446(19) 0.9780(4) 0.063(4) 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 C2 0.2(2) 0.059(11) 0.029(7) -0.004(7) -0.04(2) 0.07(2) Br1 0.15(3) 0.088(2) 0.0430(13) -0.0054(13) 0.009(4) 0.021(5) Br2 0.10(3) 0.0774(19) 0.0677(16) 0.0166(13) 0.004(4) 0.039(4) Cl1 0.15(3) 0.088(2) 0.0430(13) -0.0054(13) 0.009(4) 0.021(5) Cl2 0.10(3) 0.0774(19) 0.0677(16) 0.0166(13) 0.004(4) 0.039(4) C4 0.14(17) 0.029(8) 0.060(10) 0.009(7) -0.01(3) -0.01(2) O4 0.19(12) 0.056(7) 0.041(6) 0.007(5) -0.018(19) 0.001(19) Br3 0.11(3) 0.0445(12) 0.0635(14) 0.0008(9) -0.002(3) 0.015(3) Br4 0.10(3) 0.0613(17) 0.0406(13) -0.0079(12) -0.017(3) -0.008(4) Cl3 0.11(3) 0.0445(12) 0.0635(14) 0.0008(9) -0.002(3) 0.015(3) Cl4 0.10(3) 0.0613(17) 0.0406(13) -0.0079(12) -0.017(3) -0.008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 1.21(5) . ? C1 O2 1.27(4) . ? C1 C2 1.68(6) . ? C2 F1 1.05(5) . ? C2 Cl2 1.800(18) . ? C2 Br2 1.800(18) . ? C2 Br1 2.03(5) . ? C2 Cl1 2.03(5) . ? C3 O4 1.10(7) . ? C3 O3 1.40(6) . ? C3 C4 1.60(3) . ? C4 F2 1.37(7) . ? C4 Cl4 1.77(3) . ? C4 Br4 1.77(3) . ? C4 Br3 1.83(4) . ? C4 Cl3 1.83(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 O2 130(2) . . ? O1 C1 C2 123.2(19) . . ? O2 C1 C2 105(4) . . ? F1 C2 C1 116(2) . . ? F1 C2 Cl2 132(4) . . ? C1 C2 Cl2 107(2) . . ? F1 C2 Br2 132(4) . . ? C1 C2 Br2 107(2) . . ? Cl2 C2 Br2 0.0(7) . . ? F1 C2 Br1 94(2) . . ? C1 C2 Br1 92(3) . . ? Cl2 C2 Br1 102.8(19) . . ? Br2 C2 Br1 102.8(19) . . ? F1 C2 Cl1 94(2) . . ? C1 C2 Cl1 92(3) . . ? Cl2 C2 Cl1 102.8(19) . . ? Br2 C2 Cl1 102.8(19) . . ? Br1 C2 Cl1 0.00(19) . . ? O4 C3 O3 130(2) . . ? O4 C3 C4 127(5) . . ? O3 C3 C4 102(4) . . ? F2 C4 C3 101(5) . . ? F2 C4 Cl4 109(2) . . ? C3 C4 Cl4 117.4(14) . . ? F2 C4 Br4 109(2) . . ? C3 C4 Br4 117.4(14) . . ? Cl4 C4 Br4 0.00(11) . . ? F2 C4 Br3 106.2(14) . . ? C3 C4 Br3 108(2) . . ? Cl4 C4 Br3 114(3) . . ? Br4 C4 Br3 114(3) . . ? F2 C4 Cl3 106.2(14) . . ? C3 C4 Cl3 108(2) . . ? Cl4 C4 Cl3 114(3) . . ? Br4 C4 Cl3 114(3) . . ? Br3 C4 Cl3 0.00(16) . . ? 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 O1 C1 C2 F1 167(4) . . . . ? O2 C1 C2 F1 -28(5) . . . . ? O1 C1 C2 Cl2 -33(5) . . . . ? O2 C1 C2 Cl2 132(2) . . . . ? O1 C1 C2 Br2 -33(5) . . . . ? O2 C1 C2 Br2 132(2) . . . . ? O1 C1 C2 Br1 71(3) . . . . ? O2 C1 C2 Br1 -124(2) . . . . ? O1 C1 C2 Cl1 71(3) . . . . ? O2 C1 C2 Cl1 -124(2) . . . . ? O4 C3 C4 F2 -17(5) . . . . ? O3 C3 C4 F2 166(2) . . . . ? O4 C3 C4 Cl4 -134(4) . . . . ? O3 C3 C4 Cl4 48(5) . . . . ? O4 C3 C4 Br4 -134(4) . . . . ? O3 C3 C4 Br4 48(5) . . . . ? O4 C3 C4 Br3 95(6) . . . . ? O3 C3 C4 Br3 -83(3) . . . . ? O4 C3 C4 Cl3 95(6) . . . . ? O3 C3 C4 Cl3 -83(3) . . . . ? _diffrn_measured_fraction_theta_max 0.259 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.259 _refine_diff_density_max 0.280 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.081 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 3591.53 3619.90 118.77 o 0 2 0 92180.16 86198.31 1498.35 o 2 2 0 5046.62 5145.04 97.87 o 1 3 0 540.67 495.02 19.94 o 3 3 0 3447.36 3432.35 87.57 o 0 4 0 35.25 61.66 27.08 o 2 4 0 9603.61 10294.08 119.24 o 1 5 0 7092.61 7345.19 106.24 o 3 5 0 984.64 1125.78 119.06 o 0 6 0 212.08 454.38 123.98 o 2 6 0 22.35 51.82 63.27 o 1 7 0 202.72 152.90 125.77 o 3 7 0 91.99 185.79 177.38 o 1 1 1 11225.50 12617.00 91.19 o 0 2 1 15323.00 13326.79 168.87 o 1 2 1 8169.02 7559.97 83.31 o 2 2 1 850.89 828.74 26.44 o 1 3 1 347.28 386.33 15.09 o 2 3 1 4290.08 4059.09 49.99 o 3 3 1 1545.61 1668.74 45.60 o 0 4 1 4906.66 4900.69 61.28 o 1 4 1 1371.88 1145.44 29.52 o 2 4 1 1581.25 1520.18 43.47 o 3 4 1 3703.91 3103.62 62.68 o 1 5 1 1238.43 1201.13 45.19 o 2 5 1 128.40 75.69 38.81 o 3 5 1 3.65 76.10 37.88 o 0 6 1 846.23 685.00 87.68 o 1 6 1 58.43 114.98 54.95 o 2 6 1 22.38 112.59 44.33 o 3 6 1 358.68 286.42 78.77 o 1 7 1 0.56 128.27 76.76 o 2 7 1 1016.80 1092.47 117.45 o 3 7 1 34.88 64.60 85.51 o 1 1 2 3376.00 3710.67 57.88 o 0 2 2 11726.55 11725.77 108.89 o 1 2 2 6404.32 6146.52 65.26 o 2 2 2 14547.27 13839.08 143.81 o 1 3 2 23181.27 25124.59 181.39 o 2 3 2 20311.80 20706.81 170.10 o 3 3 2 196.90 118.50 29.89 o 0 4 2 836.59 633.14 32.26 o 1 4 2 5798.84 6542.99 45.91 o 2 4 2 1407.59 1241.35 42.30 o 3 4 2 1632.21 1357.29 54.76 o 1 5 2 4468.10 4500.65 65.59 o 2 5 2 668.66 724.35 58.19 o 3 5 2 530.97 365.18 51.74 o 4 5 2 186.24 365.96 211.87 o 0 6 2 246.57 140.66 53.82 o 1 6 2 2076.21 2490.71 109.63 o 2 6 2 284.70 241.40 67.52 o 3 6 2 969.09 956.98 94.79 o 1 7 2 7.86 157.26 76.05 o 2 7 2 16.17 172.37 69.45 o 3 7 2 3.50 89.48 179.28 o 1 1 3 6096.40 5948.23 52.20 o 2 1 3 41314.38 42849.39 288.92 o 0 2 3 22262.18 22387.89 199.65 o 1 2 3 383.12 328.03 14.09 o 2 2 3 25416.40 26418.00 168.33 o 1 3 3 3957.97 3878.59 33.89 o 2 3 3 36.95 52.78 14.99 o 3 3 3 530.25 576.63 34.06 o 0 4 3 804.36 820.22 40.57 o 1 4 3 3420.46 3740.88 43.05 o 2 4 3 1006.87 1073.39 39.28 o 3 4 3 4533.17 4690.50 83.93 o 1 5 3 6.59 288.79 84.67 o 2 5 3 4182.07 4348.70 88.03 o 3 5 3 134.46 127.09 43.76 o 4 5 3 584.15 578.44 190.03 o 0 6 3 1918.62 2378.84 123.21 o 1 6 3 43.46 113.34 52.23 o 2 6 3 187.39 117.98 46.99 o 3 6 3 3.08 103.75 58.58 o 1 7 3 333.24 238.49 91.08 o 2 7 3 220.26 196.24 82.76 o 3 7 3 188.08 158.37 142.52 o 0 0 4 1994.67 2182.17 22.79 o 1 0 4 31591.76 37227.30 276.66 o 1 1 4 6946.61 6496.97 62.11 o 2 1 4 10804.73 10919.40 143.38 o 0 2 4 9556.34 9479.77 91.45 o 1 2 4 5609.74 5216.24 44.20 o 2 2 4 12834.12 14094.05 162.35 o 3 2 4 17.36 -12.84 102.73 o 1 3 4 8683.32 8145.09 54.29 o 2 3 4 10655.40 11513.68 123.25 o 3 3 4 6027.98 6874.34 92.81 o 0 4 4 148.37 121.14 25.52 o 1 4 4 6155.93 6054.81 49.21 o 2 4 4 375.99 375.35 30.40 o 3 4 4 19617.82 20754.49 301.54 o 4 4 4 345.51 365.96 205.45 o 1 5 4 1737.06 1785.32 54.31 o 2 5 4 3782.35 3325.45 79.96 o 3 5 4 1652.67 1939.28 84.08 o 4 5 4 3459.16 3721.63 245.15 o 0 6 4 56.84 126.60 56.34 o 1 6 4 159.85 168.17 48.49 o 2 6 4 290.70 227.61 56.40 o 3 6 4 187.33 206.28 75.43 o 1 7 4 320.87 2083.18 703.94 o 2 7 4 40.10 116.68 66.76 o 3 7 4 394.82 286.78 211.87 o 1 1 5 6840.81 6008.93 63.77 o 2 1 5 18117.62 19691.41 147.17 o 0 2 5 33884.24 33248.13 211.76 o 1 2 5 2359.08 1873.26 20.52 o 2 2 5 3780.62 3939.88 85.48 o 3 2 5 1669.57 1518.10 115.70 o 1 3 5 18679.14 18028.73 176.78 o 2 3 5 2350.17 2190.26 41.91 o 3 3 5 92.92 87.50 17.83 o 0 4 5 2887.73 2160.94 55.33 o 1 4 5 13.92 75.28 16.69 o 2 4 5 361.93 389.68 31.29 o 3 4 5 2798.51 2456.19 78.49 o 4 4 5 149.23 235.86 124.62 o 1 5 5 1.36 69.82 25.07 o 2 5 5 2.51 68.25 30.92 o 3 5 5 66.92 121.53 45.92 o 4 5 5 744.48 863.45 178.94 o 0 6 5 1730.00 1770.31 102.71 o 1 6 5 83.47 101.01 36.56 o 2 6 5 444.65 456.40 62.23 o 3 6 5 72.61 164.24 72.95 o 1 7 5 839.45 705.58 115.77 o 2 7 5 455.66 431.59 90.39 o 0 0 6 5180.95 5283.02 40.39 o 1 0 6 5148.32 5534.35 42.77 o 2 0 6 11055.71 10350.60 587.46 o 1 1 6 25134.24 25234.34 168.30 o 2 1 6 138788.05 153028.86 1356.36 o 0 2 6 2456.24 1931.99 37.96 o 1 2 6 170.59 208.35 13.61 o 2 2 6 4817.82 4351.63 150.24 o 3 2 6 902.92 740.83 128.41 o 1 3 6 1254.83 1097.13 25.75 o 2 3 6 406.17 305.94 24.24 o 3 3 6 1858.27 1864.66 47.16 o 0 4 6 1937.71 1583.45 52.00 o 1 4 6 181.10 99.46 20.75 o 2 4 6 690.16 731.89 36.35 o 3 4 6 7435.86 7090.85 264.33 o 4 4 6 112.59 243.97 123.27 o 1 5 6 288.06 255.94 36.41 o 2 5 6 0.08 103.47 36.63 o 3 5 6 265.19 258.23 58.01 o 4 5 6 1905.98 2080.19 308.18 o 0 6 6 1168.64 1246.76 96.94 o 1 6 6 60.24 93.57 38.78 o 2 6 6 413.42 444.53 64.51 o 3 6 6 2039.30 2328.33 137.20 o 1 7 6 64.58 100.51 66.05 o 1 1 7 37188.58 39868.96 330.38 o 2 1 7 37.31 58.64 12.59 o 0 2 7 2853.04 2510.92 31.19 o 1 2 7 4189.52 4042.04 39.00 o 2 2 7 260.93 255.69 20.83 o 3 2 7 3070.91 2691.44 72.48 o 1 3 7 3705.85 3151.95 37.71 o 2 3 7 6305.15 6874.21 74.99 o 3 3 7 369.75 298.97 38.52 o 0 4 7 4284.73 4646.52 70.93 o 1 4 7 178.25 111.70 21.86 o 2 4 7 250.93 201.83 30.16 o 3 4 7 244.79 128.98 35.93 o 4 4 7 1048.37 1191.32 153.56 o 1 5 7 274.95 273.77 38.22 o 2 5 7 255.79 437.73 50.49 o 3 5 7 97.15 116.71 45.55 o 4 5 7 138.21 231.13 147.67 o 0 6 7 69.18 127.42 57.39 o 1 6 7 506.44 446.82 64.21 o 2 6 7 410.37 291.63 65.83 o 3 6 7 1627.42 1727.22 141.13 o 0 0 8 1027.77 1160.76 51.36 o 1 0 8 28.95 33.03 8.44 o 2 0 8 93769.87 110497.60 856.03 o 1 1 8 6076.52 6762.15 45.23 o 2 1 8 18159.21 17652.10 179.73 o 3 1 8 10851.14 10946.69 269.65 o 0 2 8 34337.54 32213.39 271.82 o 1 2 8 2516.79 2418.83 31.67 o 2 2 8 3614.59 3722.48 38.46 o 3 2 8 1176.64 1239.97 89.80 o 1 3 8 2039.25 2468.46 32.75 o 2 3 8 11678.21 11942.39 94.27 o 3 3 8 963.00 836.72 40.31 o 0 4 8 25515.58 27349.52 190.74 o 1 4 8 405.27 300.87 28.08 o 2 4 8 292.83 182.98 31.07 o 3 4 8 5335.27 5363.87 83.24 o 4 4 8 4499.77 4558.45 359.54 o 1 5 8 4834.92 5022.15 84.68 o 2 5 8 451.86 553.86 65.21 o 3 5 8 215.54 280.34 55.61 o 0 6 8 83.43 170.36 66.38 o 1 6 8 83.99 164.21 53.90 o 2 6 8 20.36 139.46 58.99 o 3 6 8 204.49 295.87 79.50 o 1 1 9 6417.32 7752.37 59.44 o 2 1 9 5775.13 6279.51 58.37 o 3 1 9 690.21 675.58 105.94 o 0 2 9 868.29 761.36 43.22 o 1 2 9 2003.66 1591.18 25.51 o 2 2 9 2294.50 1767.98 104.04 o 3 2 9 13852.33 13422.84 226.21 o 1 3 9 21.70 60.27 13.25 o 2 3 9 5739.21 5884.74 62.70 o 3 3 9 84.93 120.11 25.94 o 0 4 9 4114.64 3664.27 73.02 o 1 4 9 275.98 261.32 27.89 o 2 4 9 421.73 370.87 41.20 o 3 4 9 92.54 87.11 39.74 o 4 4 9 989.79 1020.83 186.40 o 1 5 9 588.90 537.05 47.31 o 2 5 9 194.17 187.61 54.56 o 3 5 9 7.86 109.70 50.48 o 0 6 9 556.47 395.60 94.81 o 1 6 9 222.86 224.33 56.44 o 2 6 9 3.78 112.76 51.40 o 3 6 9 793.69 661.24 118.63 o 0 0 10 35.54 57.97 18.63 o 1 0 10 95.27 112.05 17.46 o 2 0 10 211.84 175.10 24.68 o 3 0 10 288.15 430.16 166.93 o 1 1 10 17602.00 17244.45 129.74 o 2 1 10 1361.47 1152.35 28.11 o 3 1 10 106.58 144.52 32.71 o 0 2 10 75.78 81.73 15.66 o 1 2 10 21512.79 21653.30 239.25 o 2 2 10 520.11 475.31 27.20 o 3 2 10 5825.27 4684.98 378.61 o 1 3 10 4630.82 5646.79 56.99 o 2 3 10 3982.39 4077.60 85.37 o 3 3 10 15.23 685.94 308.68 o 0 4 10 5691.17 5408.48 83.26 o 1 4 10 2861.00 3086.10 52.20 o 2 4 10 64.46 85.44 26.86 o 3 4 10 762.95 654.76 61.81 o 4 4 10 50.96 56.53 79.80 o 1 5 10 1383.63 1548.52 60.00 o 2 5 10 604.63 566.42 66.29 o 3 5 10 89.26 125.34 53.21 o 0 6 10 1717.16 2015.41 126.83 o 1 6 10 385.68 240.02 60.79 o 2 6 10 127.12 88.36 51.29 o 3 6 10 236.22 227.23 114.26 o 1 1 11 40.14 86.37 12.66 o 2 1 11 10281.92 11917.98 98.48 o 3 1 11 388.32 312.29 44.90 o 0 2 11 13180.77 12720.61 136.71 o 1 2 11 189.74 106.21 15.74 o 2 2 11 260.30 262.61 25.93 o 3 2 11 11.15 62.33 22.23 o 1 3 11 620.53 741.30 34.59 o 2 3 11 4977.10 4582.50 187.47 o 3 3 11 10.36 28.49 38.75 o 0 4 11 888.46 1027.28 59.31 o 1 4 11 2089.94 1811.23 51.06 o 2 4 11 171.04 155.76 31.22 o 3 4 11 4101.45 5246.69 109.24 o 4 4 11 308.88 237.55 218.29 o 1 5 11 49.47 146.08 37.45 o 2 5 11 182.45 327.15 61.17 o 3 5 11 53.13 133.58 51.68 o 0 6 11 21.85 130.85 72.08 o 1 6 11 12.59 144.02 62.39 o 2 6 11 197.29 189.93 64.98 o 3 6 11 476.71 314.60 126.61 o 0 0 12 18597.30 20187.11 261.09 o 1 0 12 40712.62 40517.49 321.26 o 2 0 12 1669.38 1502.15 39.79 o 3 0 12 64694.48 73833.58 756.52 o 1 1 12 93.55 80.39 13.29 o 2 1 12 139.97 133.02 18.54 o 3 1 12 547.97 665.35 41.87 o 0 2 12 3589.76 3683.41 60.92 o 1 2 12 8605.82 8948.12 64.96 o 2 2 12 1072.58 802.36 38.00 o 3 2 12 20.91 62.75 38.93 o 1 3 12 71.04 74.41 20.45 o 2 3 12 22.76 68.32 23.85 o 3 3 12 1126.79 1061.28 68.02 o 0 4 12 148.83 282.47 49.31 o 1 4 12 10.68 85.58 23.65 o 2 4 12 1121.92 812.75 50.29 o 3 4 12 165.27 143.88 47.93 o 4 4 12 263.11 109.15 205.45 o 1 5 12 1.32 111.24 36.22 o 2 5 12 2563.73 2120.86 91.55 o 3 5 12 190.72 103.58 61.79 o 0 6 12 30.44 98.92 61.59 o 1 6 12 250.52 162.26 73.54 o 2 6 12 78.00 139.63 76.29 o 3 6 12 215.91 225.97 117.55 o 1 1 13 311.04 318.29 20.17 o 2 1 13 870.44 960.65 32.28 o 3 1 13 796.23 617.30 45.66 o 0 2 13 9434.90 9320.29 79.59 o 1 2 13 776.46 681.49 29.19 o 2 2 13 5541.69 5619.83 64.86 o 3 2 13 5519.40 5179.86 143.74 o 1 3 13 2558.01 2443.88 50.40 o 2 3 13 210.05 272.10 34.19 o 3 3 13 289.79 261.50 47.74 o 0 4 13 462.99 479.61 61.19 o 1 4 13 411.14 306.47 39.74 o 2 4 13 390.18 402.55 43.19 o 3 4 13 664.12 468.50 55.22 o 1 5 13 368.19 249.58 46.15 o 2 5 13 178.70 268.37 55.79 o 3 5 13 86.92 198.64 86.37 o 0 6 13 12.35 139.23 72.34 o 1 6 13 35.10 111.87 73.71 o 2 6 13 75.44 149.84 71.61 o 3 6 13 27.79 83.58 124.78 o 0 0 14 27313.82 31698.54 474.21 o 1 0 14 144.21 136.68 26.09 o 2 0 14 478.06 517.84 45.68 o 3 0 14 13417.09 14908.65 173.05 o 1 1 14 129.91 151.79 19.18 o 2 1 14 2597.77 2707.84 50.66 o 3 1 14 1079.87 801.54 49.65 o 0 2 14 3033.61 3096.72 65.92 o 1 2 14 1453.77 1591.88 35.87 o 2 2 14 1150.89 1060.23 42.06 o 3 2 14 7900.77 8552.33 194.61 o 1 3 14 2223.28 2779.40 49.73 o 2 3 14 11667.22 12001.60 125.01 o 3 3 14 784.58 753.21 116.76 o 0 4 14 1815.23 2508.89 86.63 o 1 4 14 378.12 348.74 41.09 o 2 4 14 155.68 215.23 40.52 o 3 4 14 143.53 105.91 56.61 o 1 5 14 12.98 41.59 32.20 o 2 5 14 3228.02 3578.31 120.53 o 3 5 14 17.27 89.88 74.58 o 1 1 15 4521.17 4907.85 74.98 o 2 1 15 6.34 73.57 19.96 o 3 1 15 139.45 184.12 43.67 o 0 2 15 1061.36 1062.05 58.18 o 1 2 15 476.09 291.65 27.81 o 2 2 15 190.78 226.56 33.26 o 3 2 15 4701.56 5069.87 312.73 o 1 3 15 133.94 121.18 24.90 o 2 3 15 5.64 66.53 30.25 o 3 3 15 81.74 116.75 71.59 o 0 4 15 3034.15 3208.22 101.84 o 1 4 15 216.15 100.25 31.02 o 2 4 15 733.60 643.53 69.49 o 3 4 15 10.91 128.12 64.32 o 1 5 15 999.04 1392.99 84.08 o 2 5 15 24.09 121.73 51.98 o 3 5 15 271.17 245.86 138.76 o 0 0 16 19920.79 22003.94 206.40 o 1 0 16 125.86 92.86 27.13 o 2 0 16 516.62 506.67 44.90 o 3 0 16 12666.88 14989.36 228.14 o 1 1 16 3462.19 3455.31 74.74 o 2 1 16 7538.88 7782.53 86.59 o 3 1 16 4029.11 4017.69 107.68 o 0 2 16 970.29 1100.94 58.15 o 1 2 16 7.50 126.85 40.54 o 2 2 16 1966.28 2016.99 56.53 o 3 2 16 1575.32 1182.18 131.05 o 1 3 16 2943.01 3501.54 121.70 o 2 3 16 5349.80 5553.31 91.92 o 3 3 16 1954.82 1976.92 150.95 o 0 4 16 1607.26 1315.86 82.19 o 1 4 16 506.62 567.71 60.43 o 2 4 16 706.08 532.88 77.58 o 3 4 16 2.17 110.32 79.18 o 1 5 16 134.38 163.00 51.17 o 2 5 16 1049.27 989.46 97.31 o 3 5 16 376.60 382.01 195.21 o 1 1 17 1299.76 1278.56 58.40 o 2 1 17 29.30 75.36 29.89 o 3 1 17 31.60 65.39 47.01 o 0 2 17 2683.14 2598.30 79.51 o 1 2 17 1769.12 1834.25 57.30 o 2 2 17 240.79 183.78 34.45 o 3 2 17 2244.39 2911.53 161.96 o 1 3 17 5.52 103.46 30.06 o 2 3 17 2462.96 2744.59 88.78 o 3 3 17 0.58 58.19 59.81 o 0 4 17 14.69 123.21 53.35 o 1 4 17 184.19 219.14 50.34 o 2 4 17 159.25 96.81 62.16 o 3 4 17 17.81 133.50 94.95 o 1 5 17 0.40 117.18 52.21 o 2 5 17 97.69 193.05 82.55 o 3 5 17 0.38 145.38 127.08 o 0 0 18 190.09 185.31 51.14 o 1 0 18 3335.36 3370.14 79.05 o 2 0 18 29.90 102.64 47.46 o 3 0 18 4169.04 4185.31 137.65 o 1 1 18 7835.93 9112.43 100.10 o 2 1 18 254.47 173.14 32.17 o 3 1 18 2241.05 2204.78 93.00 o 0 2 18 452.61 441.13 55.26 o 1 2 18 1853.16 1979.24 60.58 o 2 2 18 249.10 217.75 37.12 o 3 2 18 134.06 132.57 78.79 o 1 3 18 122.41 120.65 34.76 o 2 3 18 444.56 402.61 54.09 o 3 3 18 997.71 1196.05 152.72 o 0 4 18 385.52 348.11 68.34 o 1 4 18 455.96 191.80 55.50 o 2 4 18 631.69 604.96 91.18 o 3 4 18 218.05 125.50 87.45 o 1 5 18 5.53 108.32 64.42 o 1 1 19 121.97 132.51 30.88 o 2 1 19 2325.68 2486.32 78.68 o 3 1 19 69.99 150.51 62.63 o 0 2 19 577.61 514.75 62.88 o 1 2 19 0.16 118.44 29.78 o 2 2 19 155.55 134.46 40.63 o 3 2 19 116.57 121.56 75.11 o 1 3 19 25.11 122.11 42.58 o 2 3 19 732.73 524.22 69.02 o 3 3 19 20.34 128.77 89.41 o 0 4 19 101.77 171.52 86.43 o 1 4 19 9.57 113.73 58.12 o 2 4 19 0.75 103.65 64.82 o 3 4 19 561.03 345.56 148.57 o 0 0 20 1891.27 2138.49 152.25 o 1 0 20 449.33 359.85 48.82 o 2 0 20 650.04 540.61 113.22 o 3 0 20 3325.72 3511.03 229.81 o 1 1 20 1001.00 892.50 51.87 o 2 1 20 6.72 91.45 40.40 o 3 1 20 4.18 89.08 76.38 o 0 2 20 946.28 734.60 70.15 o 1 2 20 1465.40 1511.13 66.30 o 2 2 20 8.61 85.66 42.05 o 3 2 20 9.38 127.78 88.83 o 1 3 20 129.69 178.42 47.63 o 2 3 20 98.16 161.68 85.34 o 3 3 20 28.28 197.38 125.72 o 0 4 20 2516.46 2400.14 157.49 o 1 4 20 492.61 462.15 81.55 o 2 4 20 29.18 159.49 109.41 o 1 1 21 162.49 116.17 39.88 o 2 1 21 90.33 174.69 64.75 o 3 1 21 0.67 122.38 93.57 o 0 2 21 901.33 1017.60 95.10 o 1 2 21 28.61 130.52 36.16 o 2 2 21 92.12 145.16 58.91 o 3 2 21 290.76 118.97 105.71 o 1 3 21 620.62 491.67 68.52 o 2 3 21 239.34 381.85 141.69 o 3 3 21 3.00 143.29 141.66 o 0 0 22 2277.42 2056.61 189.12 o 1 0 22 182.28 190.02 77.85 o 2 0 22 623.26 559.56 147.34 o 1 1 22 172.13 144.53 41.55 o 2 1 22 1694.72 1988.12 129.56 o 3 1 22 170.82 269.65 231.13 o 0 2 22 4190.86 5319.93 164.69 o 1 2 22 154.11 170.88 46.80 o 2 2 22 7.21 149.44 68.72 o 3 2 22 31.47 100.98 127.08 o 1 3 22 334.89 260.14 57.60 o 2 3 22 246.20 128.72 80.13 o 3 3 22 53.49 269.65 263.23 o 1 1 23 888.90 949.22 80.25 o 2 1 23 28.56 169.65 78.84 o 0 2 23 22.88 81.05 65.17 o 1 2 23 335.64 345.37 69.49 o 2 2 23 25.63 134.98 83.43 o 0 0 24 3334.04 2941.31 225.55 o 1 0 24 1223.78 1172.82 171.18 o 2 0 24 599.33 279.32 97.98 o 1 1 24 417.41 546.12 103.68 o 2 1 24 903.65 686.01 127.66 o 0 2 24 126.00 134.12 64.62 o 1 2 24 652.80 609.24 102.10 o # AND data_bromochlorofluorocarboxylic_acid_2 _database_code_depnum_ccdc_archive 'CCDC 724000' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromochlorofluorocarboxylic acid ; _chemical_name_common 'bromochlorofluorocarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C2 H Br Cl F O2' _chemical_formula_sum 'C2 H Br Cl F O2' _chemical_formula_weight 191.39 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 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bcn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.169(4) _cell_length_b 6.0038(16) _cell_length_c 20.971(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2035.7(9) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3964 _cell_measurement_theta_min 3.62 _cell_measurement_theta_max 24.97 _exptl_crystal_description disc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.470 _exptl_crystal_size_mid 0.460 _exptl_crystal_size_min 0.085 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 8.503 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.32 _exptl_absorpt_correction_T_max 0.49 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; High-pressure measurement at 0.59 GPa. ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 590000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7980 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 24.97 _reflns_number_total 706 _reflns_number_gt 628 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed 2.0' _computing_publication_material 'X-seed 2.0' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+20.2760P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 706 _refine_ls_number_parameters 122 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1530 _refine_ls_wR_factor_gt 0.1475 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.1474(12) -1.041(4) 0.7427(6) 0.047(5) Uani 1 1 d . . . C2 C 1.1083(11) -0.963(3) 0.6818(6) 0.048(5) Uani 1 1 d . . . O1 O 1.2118(10) -0.928(3) 0.7591(4) 0.065(5) Uani 1 1 d . . . H1 H 1.2299 -0.9755 0.7929 0.097 Uiso 1 1 calc R . . O2 O 1.1176(8) -1.196(2) 0.7701(4) 0.057(3) Uani 1 1 d . . . Br1 Br 1.1807(2) -1.0096(6) 0.61609(9) 0.0703(10) Uani 0.34 1 d P . . Br2 Br 1.08107(17) -0.6642(5) 0.68700(9) 0.0793(10) Uani 0.66 1 d P . . Cl1 Cl 1.1807(2) -1.0096(6) 0.61609(9) 0.0703(10) Uani 0.66 1 d P . . Cl2 Cl 1.08107(17) -0.6642(5) 0.68700(9) 0.0793(10) Uani 0.34 1 d P . . F1 F 1.0430(9) -1.084(3) 0.6687(5) 0.108(6) Uani 1 1 d . . . C3 C 1.3370(11) -1.037(3) 0.8960(6) 0.038(4) Uiso 1 1 d . . . C4 C 1.3512(9) -1.164(3) 0.9601(5) 0.034(4) Uani 1 1 d . . . O3 O 1.3973(7) -0.909(2) 0.8827(4) 0.054(3) Uani 1 1 d . . . H3 H 1.3875 -0.8420 0.8495 0.082 Uiso 1 1 calc R . . O4 O 1.2749(7) -1.0768(17) 0.8667(3) 0.050(3) Uani 1 1 d . . . Br3 Br 1.42121(15) -1.4000(4) 0.94485(8) 0.0565(8) Uani 0.68 1 d P . . Br4 Br 1.39044(16) -0.9837(5) 1.02307(9) 0.0474(8) Uani 0.32 1 d P . . Cl3 Cl 1.42121(15) -1.4000(4) 0.94485(8) 0.0565(8) Uani 0.32 1 d P . . Cl4 Cl 1.39044(16) -0.9837(5) 1.02307(9) 0.0474(8) Uani 0.68 1 d P . . F2 F 1.2776(5) -1.2437(15) 0.9793(3) 0.049(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 0.07(2) 0.02(3) 0.046(7) 0.007(9) -0.007(9) -0.001(7) C2 0.07(2) 0.03(2) 0.043(6) 0.026(7) -0.014(7) -0.024(7) O1 0.092(19) 0.045(16) 0.058(5) 0.010(6) -0.034(7) -0.018(7) O2 0.053(16) 0.065(18) 0.054(5) 0.031(6) -0.005(5) -0.003(5) Br1 0.101(4) 0.076(4) 0.0336(10) -0.0047(13) 0.0059(13) 0.0137(15) Br2 0.086(3) 0.091(4) 0.0617(12) 0.0154(13) 0.0076(12) 0.0359(13) Cl1 0.101(4) 0.076(4) 0.0336(10) -0.0047(13) 0.0059(13) 0.0137(15) Cl2 0.086(3) 0.091(4) 0.0617(12) 0.0154(13) 0.0076(12) 0.0359(13) F1 0.087(15) 0.129(18) 0.107(7) 0.076(8) -0.055(7) -0.057(8) C4 0.04(2) 0.04(2) 0.024(5) 0.006(6) 0.007(6) -0.002(6) O3 0.052(14) 0.059(15) 0.053(5) 0.024(6) -0.006(5) -0.007(5) O4 0.080(15) 0.033(14) 0.037(4) 0.010(4) -0.021(5) -0.004(4) Br3 0.064(3) 0.048(3) 0.0582(11) 0.0001(10) -0.0026(10) 0.0156(9) Br4 0.050(3) 0.054(3) 0.0375(10) -0.0094(11) -0.0074(10) -0.0032(10) Cl3 0.064(3) 0.048(3) 0.0582(11) 0.0001(10) -0.0026(10) 0.0156(9) Cl4 0.050(3) 0.054(3) 0.0375(10) -0.0094(11) -0.0074(10) -0.0032(10) F2 0.021(11) 0.078(12) 0.049(4) 0.015(4) 0.000(4) -0.013(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O2 1.193(19) . ? C1 O1 1.291(19) . ? C1 C2 1.50(2) . ? C2 F1 1.311(17) . ? C2 Br1 1.829(17) . ? C2 Cl1 1.829(17) . ? C2 Br2 1.85(2) . ? C2 Cl2 1.85(2) . ? C3 O4 1.200(17) . ? C3 O3 1.274(18) . ? C3 C4 1.56(2) . ? C4 F2 1.345(16) . ? C4 Cl4 1.822(15) . ? C4 Br4 1.822(15) . ? C4 Br3 1.841(16) . ? C4 Cl3 1.841(16) . ? 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 O2 C1 O1 127.5(16) . . ? O2 C1 C2 118.9(14) . . ? O1 C1 C2 113.6(15) . . ? F1 C2 C1 110.1(12) . . ? F1 C2 Br1 105.8(13) . . ? C1 C2 Br1 108.9(14) . . ? F1 C2 Cl1 105.8(13) . . ? C1 C2 Cl1 108.9(14) . . ? Br1 C2 Cl1 0.0(2) . . ? F1 C2 Br2 111.1(18) . . ? C1 C2 Br2 110.7(12) . . ? Br1 C2 Br2 110.2(7) . . ? Cl1 C2 Br2 110.2(7) . . ? F1 C2 Cl2 111.1(18) . . ? C1 C2 Cl2 110.7(12) . . ? Br1 C2 Cl2 110.2(7) . . ? Cl1 C2 Cl2 110.2(7) . . ? Br2 C2 Cl2 0.0(2) . . ? O4 C3 O3 130.4(16) . . ? O4 C3 C4 117.9(13) . . ? O3 C3 C4 111.7(15) . . ? F2 C4 C3 107.5(11) . . ? F2 C4 Cl4 107.6(7) . . ? C3 C4 Cl4 112.7(12) . . ? F2 C4 Br4 107.6(7) . . ? C3 C4 Br4 112.7(12) . . ? Cl4 C4 Br4 0.00(8) . . ? F2 C4 Br3 108.8(12) . . ? C3 C4 Br3 108.4(10) . . ? Cl4 C4 Br3 111.7(8) . . ? Br4 C4 Br3 111.7(8) . . ? F2 C4 Cl3 108.8(12) . . ? C3 C4 Cl3 108.4(10) . . ? Cl4 C4 Cl3 111.7(8) . . ? Br4 C4 Cl3 111.7(8) . . ? Br3 C4 Cl3 0.00(15) . . ? 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 O2 C1 C2 F1 1(3) . . . . ? O1 C1 C2 F1 -179(2) . . . . ? O2 C1 C2 Br1 -115(2) . . . . ? O1 C1 C2 Br1 65(2) . . . . ? O2 C1 C2 Cl1 -115(2) . . . . ? O1 C1 C2 Cl1 65(2) . . . . ? O2 C1 C2 Br2 124(2) . . . . ? O1 C1 C2 Br2 -56(2) . . . . ? O2 C1 C2 Cl2 124(2) . . . . ? O1 C1 C2 Cl2 -56(2) . . . . ? O4 C3 C4 F2 -19(2) . . . . ? O3 C3 C4 F2 163.0(16) . . . . ? O4 C3 C4 Cl4 -137.2(14) . . . . ? O3 C3 C4 Cl4 45(2) . . . . ? O4 C3 C4 Br4 -137.2(14) . . . . ? O3 C3 C4 Br4 45(2) . . . . ? O4 C3 C4 Br3 98.6(17) . . . . ? O3 C3 C4 Br3 -79.5(19) . . . . ? O4 C3 C4 Cl3 98.6(17) . . . . ? O3 C3 C4 Cl3 -79.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.396 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.396 _refine_diff_density_max 0.363 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.091 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 2954.45 2366.86 45.57 o 3 1 0 394.54 573.50 13.12 o 5 1 0 35314.90 38507.12 267.29 o 4 2 0 18959.15 18412.50 516.64 o 6 2 0 2133.32 2065.79 37.40 o 8 2 0 132.25 105.27 27.31 o 5 3 0 6718.16 7306.95 100.38 o 7 3 0 1051.49 1020.98 50.19 o 9 3 0 3967.35 3857.43 81.33 o 11 3 0 978.64 1107.68 104.52 o 8 4 0 3146.03 3314.64 167.60 o 10 4 0 203.53 188.38 49.33 o 12 4 0 2497.38 3205.95 99.13 o 14 4 0 2483.92 2543.70 750.86 o 11 5 0 249.27 52.11 111.54 o 13 5 0 1071.30 1386.32 374.79 o 1 1 1 12398.81 10260.58 184.65 o 2 1 1 4738.41 4519.87 35.95 o 3 1 1 67.82 96.57 7.13 o 4 1 1 1237.83 1175.83 13.12 o 5 1 1 2129.39 1702.20 32.91 o 6 1 1 7426.00 7634.12 82.65 o 3 2 1 65301.84 64200.59 265.52 o 4 2 1 1611.46 1338.02 30.69 o 5 2 1 11057.57 10709.46 105.18 o 6 2 1 596.20 500.54 15.29 o 7 2 1 3459.55 3354.88 42.86 o 8 2 1 66.92 80.69 16.96 o 9 2 1 14269.07 14771.89 115.82 o 5 3 1 449.04 402.14 26.02 o 6 3 1 2413.72 2408.78 73.09 o 7 3 1 2257.00 1917.31 32.84 o 8 3 1 17.72 82.27 15.23 o 9 3 1 2399.65 2480.70 41.29 o 10 3 1 7753.72 8694.01 85.77 o 11 3 1 517.18 462.95 55.96 o 12 3 1 949.17 1032.95 64.67 o 7 4 1 1135.70 775.86 107.68 o 8 4 1 491.89 388.28 41.58 o 9 4 1 231.53 309.01 39.31 o 10 4 1 1236.52 1068.51 53.14 o 11 4 1 70.69 105.58 29.72 o 12 4 1 317.19 413.83 73.79 o 13 4 1 306.54 178.14 47.06 o 14 4 1 246.80 322.58 95.60 o 11 5 1 194.34 136.44 64.81 o 12 5 1 8.43 60.85 48.29 o 13 5 1 159.18 132.83 47.61 o 1 1 2 2386.23 3371.49 65.92 o 2 1 2 4819.43 6113.68 60.14 o 3 1 2 19461.84 18171.08 241.48 o 4 1 2 66794.86 68256.52 564.17 o 5 1 2 208.82 62.58 23.59 o 6 1 2 5884.33 6432.81 127.50 o 3 2 2 2435.74 2213.97 63.95 o 4 2 2 31239.75 32788.21 361.52 o 5 2 2 9700.15 9577.93 105.10 o 6 2 2 9614.00 9917.99 136.81 o 7 2 2 3435.04 3674.12 39.88 o 8 2 2 71.15 83.23 18.11 o 9 2 2 331.65 282.38 26.26 o 10 2 2 4190.60 4169.94 233.24 o 5 3 2 14957.42 15625.91 239.21 o 6 3 2 3329.21 3607.36 45.81 o 7 3 2 4518.26 4697.67 68.68 o 8 3 2 220.85 261.40 25.64 o 9 3 2 1080.66 1205.40 33.60 o 10 3 2 6410.25 6750.65 85.18 o 11 3 2 1498.04 1623.13 105.36 o 12 3 2 6.33 89.61 34.27 o 7 4 2 143.31 112.18 33.08 o 8 4 2 1737.72 1800.55 111.37 o 9 4 2 1050.38 1044.86 47.75 o 10 4 2 2335.42 2652.96 66.02 o 11 4 2 2.88 70.98 26.56 o 12 4 2 550.08 547.12 60.86 o 13 4 2 15.77 70.87 41.66 o 14 4 2 1232.51 1462.35 203.85 o 11 5 2 344.52 209.15 61.24 o 12 5 2 20.35 119.97 62.34 o 13 5 2 3.86 117.33 50.00 o 1 1 3 4888.33 5658.63 112.65 o 2 1 3 42690.81 39108.17 201.17 o 3 1 3 1613.76 1582.62 31.48 o 4 1 3 16713.18 15452.23 151.98 o 5 1 3 860.05 908.41 46.11 o 6 1 3 24.65 32.11 12.26 o 3 2 3 4411.99 3858.82 89.98 o 4 2 3 12827.98 11884.48 161.12 o 5 2 3 209.84 168.88 12.56 o 6 2 3 23686.79 24240.46 271.12 o 7 2 3 512.75 535.17 18.44 o 8 2 3 2403.63 2275.55 48.61 o 9 2 3 74.04 74.24 24.71 o 10 2 3 1358.93 1273.50 114.19 o 5 3 3 3516.85 3147.33 107.77 o 6 3 3 3374.72 3273.46 41.10 o 7 3 3 1881.41 1926.90 48.92 o 8 3 3 1023.22 986.78 29.87 o 9 3 3 1827.31 1798.35 38.98 o 10 3 3 3128.57 3420.19 59.44 o 11 3 3 448.16 406.55 42.47 o 12 3 3 595.22 325.09 72.31 o 7 4 3 2703.94 2205.90 266.68 o 8 4 3 43.80 82.52 30.70 o 9 4 3 1815.58 1976.04 54.93 o 10 4 3 3.52 84.22 29.18 o 11 4 3 454.66 449.61 54.99 o 12 4 3 421.23 552.94 62.00 o 13 4 3 32.38 72.45 37.28 o 14 4 3 98.03 129.89 91.61 o 11 5 3 50.08 51.38 44.23 o 12 5 3 5.29 32.64 48.38 o 13 5 3 25.15 127.35 45.88 o 0 0 4 2448.97 1947.65 45.75 o 1 0 4 32786.98 29966.55 227.38 o 2 0 4 3324.43 3343.55 284.97 o 2 1 4 11366.25 11054.94 117.96 o 3 1 4 3848.75 4694.06 39.72 o 4 1 4 24806.65 24602.17 202.72 o 5 1 4 100.05 123.02 15.27 o 6 1 4 270.82 242.39 20.31 o 2 2 4 15417.87 14104.54 1037.54 o 3 2 4 14.19 -9.79 13.96 o 4 2 4 4353.28 4144.13 54.39 o 5 2 4 97.88 89.59 10.11 o 6 2 4 8020.01 8435.88 108.27 o 7 2 4 236.60 251.20 21.39 o 8 2 4 5019.67 5055.61 126.65 o 9 2 4 467.19 445.65 39.14 o 10 2 4 501.14 361.93 72.00 o 4 3 4 6078.13 4715.81 1469.72 o 5 3 4 1378.57 1208.53 49.97 o 6 3 4 4932.19 5008.63 77.10 o 7 3 4 107.46 95.68 17.69 o 8 3 4 3743.94 4211.40 59.72 o 9 3 4 1282.28 1234.77 33.19 o 10 3 4 290.26 256.33 29.64 o 11 3 4 2306.93 2428.99 66.46 o 12 3 4 772.22 678.03 82.17 o 7 4 4 2088.16 1947.28 342.59 o 8 4 4 4674.17 5283.89 207.84 o 9 4 4 4529.81 5396.95 149.38 o 10 4 4 328.75 216.05 32.47 o 11 4 4 486.88 527.01 52.44 o 12 4 4 855.69 760.54 64.98 o 13 4 4 399.69 494.50 55.86 o 14 4 4 90.63 62.75 87.88 o 11 5 4 403.99 247.87 60.78 o 12 5 4 1231.40 1253.19 118.27 o 13 5 4 97.62 686.98 188.54 o 1 1 5 5099.01 5953.75 50.25 o 2 1 5 16190.97 15368.37 175.10 o 3 1 5 90.72 119.20 15.18 o 4 1 5 17123.64 16039.03 159.01 o 5 1 5 45.85 42.15 12.74 o 6 1 5 1056.88 915.25 79.94 o 2 2 5 4423.45 4345.33 159.48 o 3 2 5 2004.45 1740.70 57.46 o 4 2 5 1172.23 1218.33 35.34 o 5 2 5 2946.49 2748.29 33.17 o 6 2 5 20379.84 20623.87 176.59 o 7 2 5 63.62 33.69 10.54 o 8 2 5 14384.12 15339.72 207.69 o 9 2 5 1329.18 1359.37 57.17 o 10 2 5 256.34 327.57 86.63 o 4 3 5 456.04 224.05 43.03 o 5 3 5 10046.72 10299.08 256.03 o 6 3 5 130.94 98.13 19.82 o 7 3 5 5298.83 5682.24 90.69 o 8 3 5 1490.06 1569.63 36.39 o 9 3 5 552.03 591.19 31.26 o 10 3 5 12.66 55.61 18.67 o 11 3 5 2072.04 2192.42 65.16 o 12 3 5 11.15 41.40 56.85 o 7 4 5 0.73 30.75 42.78 o 8 4 5 165.74 213.05 44.48 o 9 4 5 2106.49 1997.74 119.09 o 10 4 5 17.83 60.33 23.57 o 11 4 5 851.46 799.68 53.90 o 12 4 5 128.09 195.48 63.26 o 13 4 5 31.20 73.78 38.36 o 14 4 5 80.48 147.50 102.03 o 11 5 5 352.26 331.82 111.71 o 12 5 5 92.81 67.38 40.10 o 13 5 5 68.26 128.00 41.38 o 0 0 6 5973.29 6514.32 100.94 o 1 0 6 4228.61 5189.05 51.98 o 2 0 6 12736.15 12541.13 141.65 o 3 0 6 14253.60 14128.83 156.19 o 1 1 6 23882.77 26175.21 857.87 o 2 1 6 147421.94 146766.50 1247.91 o 3 1 6 14650.65 14912.33 156.13 o 4 1 6 2060.88 1622.10 24.36 o 5 1 6 7836.75 7984.60 88.71 o 6 1 6 4.81 15.29 13.32 o 7 1 6 6583.41 7198.54 270.46 o 2 2 6 4195.80 5313.88 155.70 o 3 2 6 970.39 885.03 25.48 o 4 2 6 2999.43 2890.88 33.67 o 5 2 6 336.57 274.09 17.10 o 6 2 6 195.22 224.54 18.18 o 7 2 6 15160.14 16617.25 173.97 o 8 2 6 8095.64 8320.29 96.77 o 9 2 6 6868.21 6705.15 140.93 o 10 2 6 1207.20 1269.15 102.53 o 4 3 6 19900.98 17965.91 675.88 o 5 3 6 1190.03 1013.18 46.05 o 6 3 6 650.61 640.07 29.46 o 7 3 6 2191.40 2082.64 43.45 o 8 3 6 1330.84 1298.12 37.09 o 9 3 6 605.55 529.23 32.95 o 10 3 6 935.31 1059.45 42.81 o 11 3 6 40.91 93.53 30.23 o 12 3 6 1807.27 1290.26 203.85 o 7 4 6 1549.09 1232.03 173.93 o 8 4 6 146.83 140.09 31.62 o 9 4 6 17.73 74.45 24.66 o 10 4 6 409.49 305.24 50.46 o 11 4 6 125.29 137.16 30.20 o 12 4 6 105.49 135.20 50.73 o 13 4 6 78.73 106.98 42.38 o 14 4 6 1.45 72.31 80.74 o 11 5 6 11.24 8.30 59.77 o 12 5 6 547.26 240.54 59.82 o 1 1 7 43641.14 45257.75 929.73 o 2 1 7 66.27 86.17 18.49 o 3 1 7 2925.43 2970.88 33.34 o 4 1 7 1028.92 947.14 14.05 o 5 1 7 21941.16 21344.71 89.70 o 6 1 7 259.91 336.87 24.02 o 7 1 7 9542.42 7901.08 281.60 o 2 2 7 498.85 554.68 66.23 o 3 2 7 2309.66 2026.57 46.71 o 4 2 7 218.14 145.11 12.42 o 5 2 7 7661.13 7851.62 85.29 o 6 2 7 856.64 687.12 46.76 o 7 2 7 435.53 385.30 23.88 o 8 2 7 115.12 112.70 21.34 o 9 2 7 5404.11 5473.20 151.52 o 10 2 7 437.75 381.47 118.19 o 4 3 7 3565.49 3170.47 131.74 o 5 3 7 14255.24 12667.19 552.74 o 6 3 7 93.99 95.22 25.25 o 7 3 7 11.31 53.89 19.14 o 8 3 7 2365.46 2559.34 50.20 o 9 3 7 49.38 81.58 21.88 o 10 3 7 690.64 740.80 42.14 o 11 3 7 4120.38 4214.71 86.84 o 12 3 7 16.46 31.59 60.35 o 7 4 7 54.67 124.63 83.60 o 8 4 7 1650.95 1615.50 129.38 o 9 4 7 110.98 156.22 36.84 o 10 4 7 274.59 258.69 43.41 o 11 4 7 38.15 84.74 28.69 o 12 4 7 3106.91 3598.21 136.16 o 13 4 7 18.11 122.47 55.67 o 14 4 7 674.80 580.58 242.11 o 11 5 7 8.83 135.92 84.16 o 12 5 7 256.80 196.01 43.15 o 1 0 8 19.07 37.22 6.55 o 2 0 8 103207.93 105328.69 813.29 o 3 0 8 21087.95 19993.14 1304.12 o 4 0 8 3136.20 2672.29 144.02 o 1 1 8 5385.12 5512.91 95.75 o 2 1 8 22844.55 22461.30 318.69 o 3 1 8 9644.81 10196.11 118.09 o 4 1 8 211.91 132.67 20.18 o 5 1 8 22409.78 23430.76 350.71 o 6 1 8 5788.64 5353.17 132.38 o 7 1 8 1601.70 1278.88 100.08 o 2 2 8 4550.48 5012.92 179.76 o 3 2 8 1250.03 1304.90 35.91 o 4 2 8 1453.43 1775.42 29.07 o 5 2 8 4.62 42.48 11.28 o 6 2 8 1207.49 1109.13 26.42 o 7 2 8 5002.92 4919.31 79.56 o 8 2 8 2794.86 2760.41 50.36 o 9 2 8 513.07 409.02 36.36 o 10 2 8 51.19 29.68 47.86 o 4 3 8 612.70 520.08 69.22 o 5 3 8 12682.00 14616.87 321.50 o 6 3 8 2950.02 2991.67 59.35 o 7 3 8 263.09 166.95 26.34 o 8 3 8 22.97 75.93 21.36 o 9 3 8 1994.75 2115.47 52.68 o 10 3 8 334.95 261.01 35.43 o 11 3 8 167.70 186.99 39.10 o 12 3 8 859.41 525.18 172.94 o 7 4 8 2824.06 2859.71 368.67 o 8 4 8 2427.43 2185.06 192.98 o 9 4 8 41.18 82.04 25.71 o 10 4 8 622.37 933.76 63.04 o 11 4 8 88.55 105.73 37.88 o 12 4 8 1617.02 1770.68 75.23 o 13 4 8 107.59 120.14 56.76 o 11 5 8 456.99 438.12 398.65 o 12 5 8 293.55 253.03 85.27 o 1 1 9 7105.75 6991.65 88.76 o 2 1 9 4738.12 4839.56 53.61 o 3 1 9 1195.99 1113.23 17.20 o 4 1 9 5129.62 5627.86 65.45 o 5 1 9 12375.02 11546.60 145.39 o 6 1 9 1061.28 982.63 30.51 o 7 1 9 705.16 568.96 41.97 o 2 2 9 2782.28 2964.90 182.68 o 3 2 9 15785.90 14818.86 179.54 o 4 2 9 208.56 192.14 17.22 o 5 2 9 11657.50 12511.48 133.55 o 6 2 9 3640.10 3791.71 39.47 o 7 2 9 409.43 315.75 22.84 o 8 2 9 1879.70 1889.15 50.37 o 9 2 9 3814.08 3298.01 111.85 o 10 2 9 879.32 848.22 96.04 o 4 3 9 15330.90 17853.79 1756.81 o 5 3 9 75.45 75.43 23.23 o 6 3 9 326.02 349.93 40.20 o 7 3 9 66.20 64.86 20.22 o 8 3 9 3816.97 4325.87 73.56 o 9 3 9 51.34 97.06 24.35 o 10 3 9 1325.26 1572.87 55.75 o 11 3 9 184.52 200.54 39.34 o 12 3 9 65.48 29.14 46.11 o 7 4 9 124.84 67.01 31.79 o 8 4 9 76.69 87.99 30.30 o 9 4 9 10.08 73.22 31.35 o 10 4 9 107.72 139.83 34.97 o 11 4 9 414.20 338.70 49.45 o 12 4 9 85.18 82.17 37.81 o 13 4 9 15.31 149.50 54.81 o 11 5 9 12.50 137.35 102.47 o 0 0 10 130.57 134.33 14.27 o 1 0 10 352.32 213.34 13.69 o 2 0 10 911.95 781.64 21.44 o 3 0 10 12.12 76.44 13.35 o 4 0 10 362.19 358.19 33.89 o 1 1 10 17045.80 17500.38 203.59 o 2 1 10 831.38 867.14 22.18 o 3 1 10 487.57 504.92 15.26 o 4 1 10 5367.65 5738.92 53.55 o 5 1 10 18157.90 17544.20 136.71 o 6 1 10 7802.52 7332.06 122.60 o 7 1 10 7742.48 7713.56 297.91 o 1 2 10 20999.22 19138.55 862.44 o 2 2 10 968.12 1421.75 281.63 o 3 2 10 6250.25 6625.97 116.28 o 4 2 10 519.79 483.60 35.92 o 5 2 10 1280.37 1287.91 31.45 o 6 2 10 5886.31 6656.43 90.74 o 7 2 10 1022.05 1083.90 39.09 o 8 2 10 34.17 60.12 19.67 o 9 2 10 2326.98 1942.61 164.06 o 10 2 10 0.08 47.47 61.84 o 4 3 10 14133.06 14184.74 311.86 o 5 3 10 721.05 647.71 42.17 o 6 3 10 2979.13 2949.29 116.83 o 7 3 10 4556.27 4624.08 70.46 o 8 3 10 4222.50 4657.37 76.21 o 9 3 10 302.00 301.49 34.26 o 10 3 10 228.46 137.29 30.14 o 11 3 10 857.89 919.09 60.99 o 12 3 10 36.42 23.01 46.76 o 7 4 10 297.90 286.10 106.09 o 8 4 10 2185.55 1976.73 150.52 o 9 4 10 315.45 321.02 36.35 o 10 4 10 82.46 138.30 34.77 o 11 4 10 820.31 1021.04 65.27 o 12 4 10 259.03 174.42 37.92 o 13 4 10 707.33 556.50 75.33 o 11 5 10 496.94 457.97 293.94 o 1 1 11 123.31 105.74 12.75 o 2 1 11 13236.43 12426.69 93.25 o 3 1 11 334.21 222.49 12.44 o 4 1 11 7990.86 7554.86 81.61 o 5 1 11 245.70 262.48 37.83 o 6 1 11 989.87 806.72 37.34 o 7 1 11 1.10 44.39 31.06 o 1 2 11 186.56 424.26 55.74 o 2 2 11 98.77 54.61 13.61 o 3 2 11 1.18 34.69 18.19 o 4 2 11 1167.53 1131.59 41.42 o 5 2 11 16.90 44.79 13.67 o 6 2 11 3177.09 3307.88 58.51 o 7 2 11 308.27 304.79 30.38 o 8 2 11 660.60 619.78 50.87 o 9 2 11 538.55 202.13 46.26 o 10 2 11 193.74 212.27 77.95 o 4 3 11 489.88 526.22 48.78 o 5 3 11 1.10 25.93 22.91 o 6 3 11 10.81 60.94 21.20 o 7 3 11 2813.86 3134.96 61.31 o 8 3 11 4209.91 4377.21 81.70 o 9 3 11 34.87 72.38 25.78 o 10 3 11 223.18 215.31 34.03 o 11 3 11 102.66 148.25 43.20 o 12 3 11 21.29 84.07 67.57 o 7 4 11 314.55 230.89 82.15 o 8 4 11 0.38 93.02 32.66 o 9 4 11 1517.59 1579.56 113.53 o 10 4 11 231.60 260.97 40.00 o 11 4 11 499.06 544.88 54.43 o 12 4 11 52.56 100.98 38.49 o 13 4 11 73.44 128.59 55.44 o 0 0 12 20365.90 23036.28 285.47 o 1 0 12 38875.28 41369.20 325.02 o 2 0 12 1504.25 1342.10 31.45 o 3 0 12 68691.59 72285.13 579.72 o 4 0 12 3456.75 3652.09 80.30 o 1 1 12 35.65 56.54 11.63 o 2 1 12 182.39 198.88 19.35 o 3 1 12 432.74 466.29 18.27 o 4 1 12 2856.13 3345.41 36.72 o 5 1 12 743.04 760.98 34.89 o 6 1 12 5297.21 4870.44 82.72 o 7 1 12 934.92 853.79 71.29 o 1 2 12 10114.29 9809.10 432.90 o 2 2 12 644.12 487.93 92.66 o 3 2 12 109.02 95.59 21.84 o 4 2 12 454.07 460.63 26.18 o 5 2 12 246.14 311.82 26.05 o 6 2 12 5.23 61.34 19.82 o 7 2 12 1489.57 1534.08 40.94 o 8 2 12 810.94 674.20 72.97 o 9 2 12 511.53 347.90 58.24 o 10 2 12 905.20 950.00 558.32 o 4 3 12 440.81 370.00 70.68 o 5 3 12 2249.35 2330.52 79.51 o 6 3 12 3606.95 3156.10 170.87 o 7 3 12 100.61 96.04 27.40 o 8 3 12 429.31 374.20 40.00 o 9 3 12 764.97 687.25 50.83 o 10 3 12 3131.55 3409.76 90.94 o 11 3 12 243.91 124.40 42.25 o 12 3 12 156.92 137.66 72.55 o 7 4 12 8.67 128.57 91.17 o 8 4 12 48.27 63.21 41.45 o 9 4 12 750.22 691.34 84.47 o 10 4 12 40.67 64.63 30.12 o 11 4 12 1782.99 2064.56 89.66 o 12 4 12 166.48 216.57 45.46 o 1 1 13 124.47 95.76 12.79 o 2 1 13 949.29 930.22 26.46 o 3 1 13 457.70 560.21 21.84 o 4 1 13 3479.85 3099.57 111.76 o 5 1 13 346.17 439.29 77.10 o 6 1 13 580.68 524.91 57.04 o 7 1 13 4.72 20.61 48.74 o 1 2 13 1022.50 1200.65 97.78 o 2 2 13 7070.54 6766.41 276.02 o 3 2 13 6353.59 6873.83 248.00 o 4 2 13 3400.12 3126.91 125.40 o 5 2 13 756.40 569.38 44.06 o 6 2 13 5119.34 5710.60 85.48 o 7 2 13 1812.65 1867.92 44.91 o 8 2 13 1674.81 1715.65 94.62 o 9 2 13 2339.59 1970.54 258.11 o 4 3 13 8.62 32.75 44.90 o 5 3 13 212.88 166.39 30.26 o 6 3 13 221.58 193.24 33.12 o 7 3 13 4559.11 5341.78 119.05 o 8 3 13 505.15 440.66 36.23 o 9 3 13 288.72 243.17 41.92 o 10 3 13 476.77 374.57 45.21 o 11 3 13 5.53 31.47 35.79 o 12 3 13 188.05 203.49 92.00 o 7 4 13 117.95 126.18 95.91 o 8 4 13 35.53 252.13 123.37 o 9 4 13 150.97 193.98 56.41 o 10 4 13 54.71 116.28 36.19 o 11 4 13 3.68 111.61 38.35 o 12 4 13 49.79 139.39 39.75 o 0 0 14 43709.23 50735.13 539.45 o 1 0 14 83.63 101.68 16.21 o 2 0 14 43.73 47.71 13.05 o 3 0 14 15139.85 15044.43 735.58 o 4 0 14 7895.28 8481.65 106.91 o 1 1 14 590.51 501.37 31.31 o 2 1 14 1359.12 1570.31 36.57 o 3 1 14 821.18 862.47 24.87 o 4 1 14 11571.15 11758.26 99.21 o 5 1 14 10159.36 10181.85 146.62 o 6 1 14 770.48 603.70 64.80 o 7 1 14 10.92 83.14 87.09 o 1 2 14 1911.61 2018.23 209.96 o 2 2 14 1137.74 1121.38 114.60 o 3 2 14 8649.75 9161.65 334.77 o 4 2 14 1622.59 1525.57 159.80 o 5 2 14 1251.28 1194.74 37.69 o 6 2 14 2281.96 2991.09 60.36 o 7 2 14 10877.90 12216.32 139.09 o 8 2 14 151.06 155.41 29.66 o 9 2 14 25.57 61.64 39.96 o 4 3 14 1319.95 1235.38 72.35 o 5 3 14 5.10 58.68 27.20 o 6 3 14 91.41 71.75 26.32 o 7 3 14 528.14 522.20 41.15 o 8 3 14 2406.75 2367.50 85.16 o 9 3 14 761.01 837.59 56.51 o 10 3 14 654.97 713.50 57.59 o 11 3 14 271.60 232.57 96.62 o 8 4 14 7.42 63.56 54.82 o 9 4 14 228.54 130.75 48.27 o 10 4 14 7.91 105.54 36.38 o 11 4 14 901.88 859.28 91.83 o 1 1 15 6079.69 5710.94 179.72 o 2 1 15 1.53 25.23 12.38 o 3 1 15 339.83 367.64 22.79 o 4 1 15 124.16 118.66 25.13 o 5 1 15 4810.50 4906.79 99.18 o 6 1 15 68.66 140.63 39.94 o 7 1 15 2810.62 2396.88 444.57 o 1 2 15 140.93 119.54 38.35 o 2 2 15 197.49 218.66 33.34 o 3 2 15 3703.27 4007.29 60.52 o 4 2 15 155.54 84.50 32.77 o 5 2 15 8.30 46.89 19.71 o 6 2 15 1818.10 1953.32 56.32 o 7 2 15 214.71 156.42 32.76 o 8 2 15 6.04 74.49 29.17 o 9 2 15 668.42 611.38 78.80 o 4 3 15 47.49 68.65 37.47 o 5 3 15 219.41 172.99 41.90 o 6 3 15 151.29 112.91 32.38 o 7 3 15 2203.04 2584.29 97.90 o 8 3 15 453.46 400.70 51.20 o 9 3 15 47.08 112.99 36.70 o 10 3 15 11.25 42.10 33.10 o 11 3 15 79.32 114.46 65.81 o 8 4 15 68.76 77.42 44.73 o 9 4 15 245.31 235.19 60.92 o 10 4 15 818.62 763.80 77.33 o 0 0 16 16873.09 20326.33 255.94 o 1 0 16 9.10 24.53 26.18 o 2 0 16 489.11 521.98 30.30 o 3 0 16 14439.33 13972.28 661.13 o 4 0 16 23.85 12.25 34.03 o 1 1 16 3834.95 4090.11 82.44 o 2 1 16 5674.73 6151.45 143.09 o 3 1 16 4187.89 4794.87 77.03 o 4 1 16 1829.55 1955.07 50.27 o 5 1 16 19.18 80.94 23.13 o 6 1 16 1348.57 1219.59 82.90 o 7 1 16 55.83 77.12 72.85 o 1 2 16 23.66 77.60 51.03 o 2 2 16 2239.89 2037.83 137.49 o 3 2 16 1558.41 1547.74 75.56 o 4 2 16 876.77 803.09 49.22 o 5 2 16 972.61 1168.11 48.86 o 6 2 16 897.50 762.87 47.82 o 7 2 16 3639.54 3508.30 198.86 o 8 2 16 349.07 262.65 39.77 o 9 2 16 170.42 173.38 58.69 o 4 3 16 19.73 79.03 41.31 o 5 3 16 1004.53 1240.54 89.27 o 6 3 16 48.68 66.49 31.22 o 7 3 16 249.51 274.72 44.76 o 8 3 16 238.78 198.00 45.66 o 9 3 16 356.94 443.65 61.01 o 10 3 16 106.37 129.95 37.05 o 11 3 16 574.31 439.76 95.22 o 8 4 16 58.48 68.45 44.11 o 9 4 16 474.36 544.66 88.82 o 10 4 16 403.20 460.62 71.38 o 1 1 17 1308.33 1260.90 33.90 o 2 1 17 25.35 84.34 22.70 o 3 1 17 1.32 65.85 19.87 o 4 1 17 29.23 84.52 24.78 o 5 1 17 383.70 288.91 35.78 o 6 1 17 57.57 72.37 26.84 o 7 1 17 1558.20 793.37 164.37 o 1 2 17 2030.31 2004.50 320.39 o 2 2 17 372.67 415.79 59.85 o 3 2 17 3210.30 2923.34 187.89 o 4 2 17 312.81 314.40 32.89 o 5 2 17 821.34 849.61 44.58 o 6 2 17 3194.65 3370.99 115.27 o 7 2 17 2.16 75.71 27.19 o 8 2 17 186.43 121.52 46.51 o 9 2 17 1490.37 1382.87 248.70 o 4 3 17 591.52 410.77 165.41 o 5 3 17 77.56 88.23 53.88 o 6 3 17 189.09 127.76 32.42 o 7 3 17 8.00 64.07 29.67 o 8 3 17 225.12 225.81 42.20 o 9 3 17 557.24 539.56 60.28 o 10 3 17 321.37 232.22 47.56 o 11 3 17 16.13 85.29 86.38 o 8 4 17 325.79 197.59 69.38 o 9 4 17 99.60 157.87 61.81 o 0 0 18 259.07 346.43 42.79 o 1 0 18 2970.42 3146.52 54.66 o 2 0 18 11.76 25.69 22.14 o 3 0 18 5420.52 5656.35 92.47 o 4 0 18 18.40 63.59 30.24 o 1 1 18 11341.88 12150.75 189.32 o 2 1 18 124.51 167.26 39.96 o 3 1 18 2876.70 2944.95 56.33 o 4 1 18 1268.27 1275.24 51.21 o 5 1 18 2201.02 2513.10 101.53 o 6 1 18 536.40 467.98 88.93 o 7 1 18 1849.56 1020.28 423.49 o 1 2 18 1532.67 1394.23 148.02 o 2 2 18 384.57 412.72 66.55 o 3 2 18 24.30 55.26 31.60 o 4 2 18 432.00 392.39 39.79 o 5 2 18 869.97 819.02 45.64 o 6 2 18 684.01 636.30 40.86 o 7 2 18 4.37 322.68 98.84 o 8 2 18 3423.08 3674.80 373.82 o 5 3 18 194.39 184.25 57.69 o 6 3 18 139.89 147.44 34.22 o 7 3 18 363.03 363.54 62.86 o 8 3 18 28.17 60.26 30.93 o 9 3 18 394.32 367.85 53.81 o 10 3 18 247.00 138.55 54.77 o 1 1 19 170.75 183.23 31.70 o 2 1 19 3036.85 3336.02 68.19 o 3 1 19 133.61 87.50 24.65 o 4 1 19 4143.01 4830.43 96.40 o 5 1 19 55.09 111.81 29.81 o 6 1 19 74.61 111.64 72.66 o 7 1 19 113.70 149.56 119.50 o 1 2 19 2.73 147.84 163.50 o 2 2 19 124.87 131.53 48.44 o 3 2 19 72.08 53.44 29.69 o 4 2 19 180.12 176.35 46.09 o 5 2 19 411.31 441.07 43.24 o 6 2 19 195.61 155.97 33.96 o 7 2 19 40.61 84.36 34.07 o 8 2 19 132.59 98.32 43.18 o 9 2 19 15.76 92.52 97.49 o 5 3 19 228.66 131.10 60.95 o 6 3 19 113.75 133.75 53.17 o 7 3 19 25.38 102.32 34.59 o 8 3 19 396.32 255.59 43.34 o 9 3 19 1.72 73.48 38.60 o 0 0 20 2491.64 2959.99 88.83 o 1 0 20 499.55 377.80 63.66 o 2 0 20 492.32 481.14 52.83 o 3 0 20 4954.86 5431.60 146.94 o 4 0 20 382.18 350.73 83.17 o 1 1 20 1649.35 1780.52 136.04 o 2 1 20 370.59 337.82 40.40 o 3 1 20 6.01 68.92 32.88 o 4 1 20 1667.80 1449.68 81.53 o 5 1 20 4502.98 5273.59 126.21 o 6 1 20 448.74 283.13 71.72 o 2 2 20 2.89 93.61 46.76 o 3 2 20 132.36 109.12 39.22 o 4 2 20 826.99 640.59 80.15 o 5 2 20 31.76 99.70 31.82 o 6 2 20 0.85 92.95 32.53 o 7 2 20 425.45 271.44 47.27 o 8 2 20 253.73 405.86 98.11 o 5 3 20 1004.89 798.34 109.48 o 6 3 20 143.54 91.22 71.96 o 7 3 20 217.27 213.86 42.32 o 8 3 20 878.90 687.34 103.56 o 1 1 21 12.18 42.17 38.38 o 2 1 21 46.44 99.59 32.64 o 3 1 21 1.84 84.03 37.51 o 4 1 21 86.44 112.66 38.38 o 5 1 21 18.99 119.98 42.26 o 6 1 21 56.38 80.47 92.31 o 2 2 21 130.11 100.49 50.72 o 3 2 21 514.68 681.01 93.26 o 4 2 21 52.23 96.63 39.55 o 5 2 21 598.81 520.34 67.20 o 6 2 21 724.55 804.53 54.54 o 7 2 21 88.32 132.27 45.52 o 8 2 21 125.42 163.60 90.84 o 5 3 21 410.61 200.05 64.17 o 6 3 21 0.35 2.76 74.81 o 0 0 22 1783.15 1590.07 163.25 o 1 0 22 414.56 464.65 50.10 o 2 0 22 1137.54 1124.61 158.31 o 3 0 22 7.78 108.01 53.53 o 1 1 22 193.43 122.35 37.62 o 2 1 22 1337.92 1209.58 104.45 o 3 1 22 376.02 212.10 46.90 o 4 1 22 504.00 446.32 62.58 o 5 1 22 4219.33 4380.34 175.71 o 6 1 22 300.02 170.95 100.14 o 2 2 22 16.45 53.21 64.46 o 3 2 22 80.12 111.50 63.22 o 4 2 22 2025.14 2170.46 241.60 o 5 2 22 11.05 78.43 32.80 o 6 2 22 32.02 79.41 31.58 o 7 2 22 108.76 99.61 45.53 o 1 1 23 1144.46 1325.97 87.81 o 2 1 23 111.51 113.78 42.03 o 3 1 23 3.55 84.67 34.79 o 4 1 23 33.73 74.74 38.73 o 5 1 23 421.02 518.07 112.31 o 6 1 23 164.16 78.34 70.24 o 3 2 23 181.67 193.56 76.64 o 4 2 23 5.59 62.64 51.24 o 5 2 23 0.98 82.45 42.30 o 0 0 24 3145.97 2478.03 133.13 o 1 0 24 2100.55 1958.70 294.04 o 2 0 24 669.93 554.92 117.69 o 3 0 24 103.85 241.40 108.04 o 1 1 24 553.54 515.92 73.46 o 2 1 24 748.83 658.34 66.89 o 3 1 24 372.86 287.71 49.42 o 4 1 24 128.60 89.65 71.45 o # AND data_bromochlorofluorocarboxylic_acid_3 _database_code_depnum_ccdc_archive 'CCDC 724001' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromochlorofluorocarboxylic acid ; _chemical_name_common 'bromochlorofluorocarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C2 H Br Cl F O2' _chemical_formula_sum 'C2 H Br Cl F O2' _chemical_formula_weight 191.39 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 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.898(2) _cell_length_b 7.840(3) _cell_length_c 8.043(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.553(14) _cell_angle_gamma 90.00 _cell_volume 495.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1261 _cell_measurement_theta_min 3.64 _cell_measurement_theta_max 25.0 _exptl_crystal_description disc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.470 _exptl_crystal_size_mid 0.460 _exptl_crystal_size_min 0.085 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 8.731 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.33 _exptl_absorpt_correction_T_max 0.488 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; High-pressure measurement at 0.80 GPa. ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 800000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2252 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 320 _reflns_number_gt 308 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed 2.0' _computing_publication_material 'X-seed 2.0' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0959P)^2^+4.4939P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 320 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.4764(4) 0.1409(4) -0.1938(3) 0.0499(13) Uani 0.451(9) 1 d P . . Br2 Br 0.2447(3) -0.0256(3) -0.4786(2) 0.0462(11) Uani 0.549(9) 1 d P . . Cl1 Cl 0.4764(4) 0.1409(4) -0.1938(3) 0.0499(13) Uani 0.549(9) 1 d P . . Cl2 Cl 0.2447(3) -0.0256(3) -0.4786(2) 0.0462(11) Uani 0.451(9) 1 d P . . F1 F 0.2103(14) 0.2788(14) -0.3476(11) 0.058(3) Uani 1 1 d . . . C1 C 0.138(2) 0.057(2) -0.1712(17) 0.031(4) Uiso 1 1 d . . . C2 C 0.2589(19) 0.1204(18) -0.2967(15) 0.027(3) Uiso 1 1 d . . . O1 O 0.1882(15) -0.0742(14) -0.0870(12) 0.039(3) Uani 1 1 d . . . O2 O 0.0064(16) 0.1356(16) -0.1606(12) 0.040(3) Uani 1 1 d . . . H1 H 0.1234 -0.0926 -0.0153 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.026(4) 0.076(4) 0.0472(18) -0.0016(12) -0.002(2) -0.0111(10) Br2 0.048(4) 0.058(3) 0.0324(15) -0.0090(9) 0.0065(19) -0.0008(8) Cl1 0.026(4) 0.076(4) 0.0472(18) -0.0016(12) -0.002(2) -0.0111(10) Cl2 0.048(4) 0.058(3) 0.0324(15) -0.0090(9) 0.0065(19) -0.0008(8) F1 0.098(14) 0.017(12) 0.065(6) 0.022(5) 0.037(8) 0.008(4) O1 0.046(15) 0.030(15) 0.043(6) 0.007(5) 0.018(8) 0.006(4) O2 0.030(16) 0.055(15) 0.033(6) 0.005(5) 0.003(8) 0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br1 C2 1.840(16) . ? Br2 C2 1.853(13) . ? Cl1 C2 1.840(16) . ? Cl2 C2 1.853(13) . ? F1 C2 1.352(17) . ? C1 O2 1.220(18) . ? C1 O1 1.273(17) . ? C1 C2 1.536(19) . ? 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 O2 C1 O1 126.4(12) . . ? O2 C1 C2 118.1(13) . . ? O1 C1 C2 115.5(12) . . ? F1 C2 C1 108.7(10) . . ? F1 C2 Br1 106.3(9) . . ? C1 C2 Br1 110.2(10) . . ? F1 C2 Cl1 106.3(9) . . ? C1 C2 Cl1 110.2(10) . . ? Br1 C2 Cl1 0.0(2) . . ? F1 C2 Br2 109.5(9) . . ? C1 C2 Br2 109.0(10) . . ? Br1 C2 Br2 113.1(7) . . ? Cl1 C2 Br2 113.1(7) . . ? F1 C2 Cl2 109.5(9) . . ? C1 C2 Cl2 109.0(10) . . ? Br1 C2 Cl2 113.1(7) . . ? Cl1 C2 Cl2 113.1(7) . . ? Br2 C2 Cl2 0.00(15) . . ? 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 O2 C1 C2 F1 13(2) . . . . ? O1 C1 C2 F1 -166.1(14) . . . . ? O2 C1 C2 Br1 129.6(16) . . . . ? O1 C1 C2 Br1 -50.0(17) . . . . ? O2 C1 C2 Cl1 129.6(16) . . . . ? O1 C1 C2 Cl1 -50.0(17) . . . . ? O2 C1 C2 Br2 -105.8(17) . . . . ? O1 C1 C2 Br2 74.6(16) . . . . ? O2 C1 C2 Cl2 -105.8(17) . . . . ? O1 C1 C2 Cl2 74.6(16) . . . . ? _diffrn_measured_fraction_theta_max 0.366 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.366 _refine_diff_density_max 0.564 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.125 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 1132.67 1099.01 12.58 o 2 1 0 104.60 104.29 1.73 o 1 2 0 480.82 491.97 7.06 o 2 2 0 6094.58 5849.88 84.40 o 3 2 0 12.46 8.02 1.25 o 2 3 0 439.57 447.92 10.23 o 3 3 0 1961.29 1888.14 24.58 o 4 3 0 161.98 141.72 5.86 o 5 3 0 28.40 20.07 4.08 o 2 4 0 8049.89 5908.32 351.86 o 3 4 0 191.34 175.42 3.60 o 4 4 0 92.25 85.88 3.56 o 5 4 0 560.51 609.84 7.90 o 3 5 0 240.17 213.28 13.84 o 4 5 0 228.20 246.22 6.96 o 5 5 0 1551.40 1761.39 28.93 o 6 5 0 90.38 87.43 4.04 o 4 6 0 501.08 345.28 24.82 o 5 6 0 47.75 35.52 4.82 o 6 6 0 52.92 46.58 3.84 o 7 6 0 3.18 3.20 2.93 o 6 7 0 18.05 9.16 3.73 o -3 1 1 622.57 582.46 22.20 o -2 1 1 7344.37 7662.19 63.87 o -1 1 1 2408.66 2466.38 11.91 o 0 1 1 1074.58 1208.54 14.29 o 1 1 1 3113.75 3210.87 42.50 o -4 2 1 1967.02 1974.18 18.88 o -3 2 1 1040.41 1004.98 10.65 o -2 2 1 4827.04 4806.24 46.32 o 1 2 1 4250.72 3990.45 42.13 o 2 2 1 7613.80 7853.17 81.97 o 3 2 1 639.44 604.91 5.12 o -5 3 1 464.70 408.41 6.89 o -4 3 1 4661.04 5050.84 32.81 o -3 3 1 1322.21 1252.24 17.80 o -2 3 1 56.68 51.20 2.52 o 1 3 1 230.65 174.43 14.20 o 2 3 1 2772.85 2891.96 29.09 o 3 3 1 164.74 186.34 2.65 o 4 3 1 1656.93 1644.09 20.66 o -6 4 1 13.19 13.11 2.58 o -5 4 1 212.76 235.58 4.56 o -4 4 1 25.57 27.94 2.12 o -3 4 1 230.56 206.29 3.72 o 2 4 1 211.86 217.69 4.92 o 3 4 1 639.86 661.81 6.94 o 4 4 1 568.35 601.34 6.02 o 5 4 1 92.94 60.68 7.70 o -6 5 1 39.06 47.60 4.95 o -5 5 1 0.18 3.39 1.53 o -4 5 1 749.49 869.39 23.18 o 3 5 1 191.85 195.19 5.23 o 4 5 1 173.65 206.99 4.87 o 5 5 1 25.10 13.72 2.50 o 6 5 1 46.44 30.66 4.78 o -7 6 1 39.87 30.89 4.36 o -6 6 1 1.22 3.23 2.32 o -5 6 1 260.02 232.55 40.01 o 4 6 1 796.42 878.88 21.65 o 5 6 1 57.56 59.11 6.04 o 6 6 1 73.69 75.06 10.73 o -6 7 1 124.65 80.85 32.22 o 5 7 1 51.49 27.04 5.48 o 6 7 1 0.95 3.95 2.65 o -2 0 2 16646.69 16312.18 283.03 o -1 0 2 4866.41 4955.90 42.34 o 0 0 2 56.84 80.16 2.32 o -3 1 2 21.82 37.66 2.20 o -2 1 2 5905.58 5911.46 61.92 o -1 1 2 5606.60 5686.55 48.62 o 0 1 2 532.25 552.54 6.27 o 1 1 2 274.29 261.35 18.44 o -4 2 2 4649.61 4849.33 47.77 o -3 2 2 206.56 238.48 3.21 o -2 2 2 7755.21 7812.29 69.99 o 0 2 2 8039.61 8664.18 42.08 o 1 2 2 101.38 94.30 1.21 o 2 2 2 1152.03 1142.67 10.25 o -5 3 2 721.13 662.16 11.03 o -4 3 2 947.74 929.97 11.81 o -3 3 2 61.40 47.79 2.57 o -2 3 2 49.84 38.44 6.95 o 1 3 2 1467.15 1569.72 12.34 o 2 3 2 374.23 380.63 3.60 o 3 3 2 833.46 918.00 14.04 o 4 3 2 62.83 40.80 8.07 o -6 4 2 145.11 147.33 4.81 o -5 4 2 12.83 10.01 2.29 o -4 4 2 1294.31 1408.97 17.10 o -3 4 2 401.22 364.41 20.31 o 1 4 2 2215.95 1775.41 58.08 o 2 4 2 89.21 92.45 2.36 o 3 4 2 327.42 326.38 5.11 o 4 4 2 4836.13 5333.90 67.58 o -7 5 2 624.47 601.04 66.41 o -6 5 2 905.75 1125.98 11.42 o -5 5 2 4.93 5.31 2.19 o -4 5 2 330.45 250.66 24.43 o 2 5 2 104.73 91.03 6.15 o 3 5 2 216.83 231.77 3.96 o 4 5 2 117.15 117.46 3.27 o 5 5 2 5.83 4.44 2.01 o -7 6 2 18.84 13.46 4.01 o -6 6 2 55.40 46.18 6.17 o -5 6 2 23.14 291.46 12.21 o 3 6 2 127.12 95.08 4.81 o 4 6 2 11.38 8.33 3.67 o 5 6 2 112.22 117.67 6.04 o 6 6 2 222.43 217.01 17.24 o 5 7 2 119.44 118.97 12.33 o -4 1 3 3605.47 3631.61 52.78 o -3 1 3 4073.76 4105.00 57.65 o -2 1 3 4.45 9.73 0.63 o -1 1 3 566.20 715.99 39.32 o 0 1 3 15754.85 15782.23 412.24 o 1 1 3 2044.69 1904.73 105.53 o -5 2 3 5.11 5.44 1.54 o -4 2 3 24.43 21.84 1.58 o -3 2 3 44.41 48.91 1.60 o -2 2 3 27.86 28.89 4.17 o -1 2 3 859.43 964.79 8.84 o 0 2 3 3464.93 3903.19 25.29 o 1 2 3 253.68 306.72 4.42 o 2 2 3 12.16 11.83 1.45 o -6 3 3 2158.82 2036.89 120.36 o -5 3 3 1084.15 1138.20 20.00 o -4 3 3 160.49 176.69 3.80 o -3 3 3 24.39 19.67 1.55 o 0 3 3 6.10 6.74 1.60 o 1 3 3 1.40 6.93 0.82 o 2 3 3 5806.12 5541.98 162.57 o 3 3 3 704.48 726.28 20.60 o -6 4 3 36.22 27.23 2.61 o -5 4 3 412.79 475.01 5.51 o -4 4 3 340.84 231.29 17.66 o 1 4 3 1844.60 1925.60 24.66 o 2 4 3 913.71 1029.65 8.21 o 3 4 3 459.65 490.13 5.85 o 4 4 3 29.57 24.43 3.13 o -7 5 3 51.45 41.92 4.42 o -6 5 3 617.43 689.86 8.94 o -5 5 3 331.20 276.10 19.37 o 2 5 3 1286.19 1341.99 90.38 o 3 5 3 46.39 51.26 3.02 o 4 5 3 95.21 101.10 3.93 o 5 5 3 0.22 3.19 2.16 o -6 6 3 6.37 5.05 2.84 o 3 6 3 4.42 5.76 2.33 o 4 6 3 15.10 13.08 4.03 o 5 6 3 595.46 720.44 20.61 o 4 7 3 98.11 113.18 8.92 o 5 7 3 2.28 3.61 2.58 o -3 0 4 195.05 189.00 4.19 o -2 0 4 3071.55 3184.80 40.78 o -1 0 4 116.06 120.43 3.04 o 0 0 4 1080.18 669.62 7.31 o -4 1 4 203.87 205.24 3.07 o -3 1 4 1330.86 1272.47 47.46 o -2 1 4 4761.62 5033.39 31.84 o -1 1 4 185.70 163.70 11.93 o 0 1 4 1268.71 1334.25 14.98 o 1 1 4 1702.30 1124.17 31.42 o -5 2 4 352.94 422.66 6.93 o -4 2 4 1671.03 1862.43 19.98 o -3 2 4 988.20 1027.34 18.48 o -2 2 4 1671.83 1458.84 83.45 o -1 2 4 1272.08 1362.26 12.50 o 0 2 4 2632.10 2433.68 152.26 o 1 2 4 593.21 565.84 5.93 o 2 2 4 2861.87 2234.31 72.85 o -6 3 4 477.02 437.81 7.60 o -5 3 4 39.75 32.63 2.78 o -4 3 4 89.96 82.85 4.87 o -3 3 4 957.17 830.25 54.41 o -1 3 4 3.76 4.04 1.67 o 0 3 4 674.14 798.72 7.64 o 1 3 4 74.01 237.20 61.21 o 2 3 4 947.85 987.95 17.42 o 3 3 4 273.15 227.08 14.24 o -7 4 4 383.39 374.79 49.13 o -6 4 4 0.95 4.90 1.82 o -5 4 4 20.78 15.98 2.45 o -4 4 4 896.50 813.85 64.23 o 0 4 4 439.17 398.46 11.18 o 1 4 4 29.73 27.85 2.42 o 2 4 4 716.40 869.12 6.27 o 3 4 4 998.14 1030.77 12.48 o -7 5 4 0.46 6.34 2.95 o -6 5 4 9.79 11.63 2.92 o -5 5 4 456.01 224.84 111.31 o 1 5 4 6.81 4.28 2.10 o 2 5 4 352.43 379.03 25.71 o 3 5 4 645.85 777.77 8.30 o 4 5 4 553.21 563.57 25.84 o 3 6 4 51.50 44.82 5.15 o 4 6 4 292.94 360.65 10.69 o 5 6 4 66.69 33.07 8.40 o 4 7 4 61.95 56.82 7.27 o -5 1 5 1748.96 1740.07 46.25 o -4 1 5 192.15 202.08 3.73 o -3 1 5 554.42 607.01 5.47 o -2 1 5 5313.08 5881.34 55.51 o -1 1 5 3299.56 3637.40 36.03 o 0 1 5 399.82 380.68 4.97 o -6 2 5 257.77 239.84 12.91 o -5 2 5 194.12 236.85 4.73 o -4 2 5 1677.63 1747.74 17.61 o -3 2 5 92.26 74.65 7.41 o -2 2 5 42.35 51.46 2.71 o -1 2 5 188.39 187.86 2.82 o 0 2 5 945.66 925.62 7.81 o 1 2 5 523.63 507.80 21.78 o -6 3 5 6.67 5.68 2.87 o -5 3 5 136.17 112.52 5.34 o -4 3 5 1677.19 1814.53 9.87 o -1 3 5 57.26 61.18 3.13 o 0 3 5 3363.06 3853.71 58.44 o 1 3 5 1697.19 1880.38 8.64 o 2 3 5 30.81 25.31 2.72 o -7 4 5 47.90 53.13 8.67 o -6 4 5 244.59 251.73 10.97 o -5 4 5 46.12 10.49 3.90 o 0 4 5 613.42 708.54 13.46 o 1 4 5 466.83 519.53 5.11 o 2 4 5 136.81 128.89 7.71 o 3 4 5 550.57 525.03 32.98 o -6 5 5 1.82 2.05 2.46 o 1 5 5 333.27 334.60 18.14 o 2 5 5 16.01 24.71 2.89 o 3 5 5 25.47 23.78 2.97 o 4 5 5 239.19 224.35 58.28 o 2 6 5 79.37 51.72 9.67 o 3 6 5 371.53 347.86 14.90 o 4 6 5 16.15 7.69 3.28 o -4 0 6 3014.27 3379.81 58.62 o -3 0 6 2853.30 3250.24 30.11 o -2 0 6 0.89 3.32 1.30 o -1 0 6 594.81 459.06 21.41 o -5 1 6 8.71 9.63 2.56 o -4 1 6 9.82 15.97 2.26 o -3 1 6 410.96 391.37 16.08 o -2 1 6 255.11 252.51 13.24 o -1 1 6 100.74 110.87 3.78 o 0 1 6 733.99 576.63 14.51 o -6 2 6 198.27 207.73 13.13 o -5 2 6 322.51 361.84 5.45 o -4 2 6 15.16 21.74 2.90 o -3 2 6 442.14 413.19 12.50 o -2 2 6 393.54 417.75 9.01 o -1 2 6 1156.48 1271.52 8.36 o 0 2 6 287.12 350.08 4.46 o 1 2 6 708.73 513.43 21.02 o -6 3 6 23.67 2.62 6.31 o -5 3 6 217.00 234.70 9.48 o -4 3 6 70.48 41.48 7.58 o -1 3 6 176.97 207.05 5.41 o 0 3 6 301.58 315.11 7.24 o 1 3 6 54.79 52.88 3.05 o 2 3 6 3.92 1.42 3.39 o -6 4 6 513.15 521.29 68.43 o 0 4 6 51.06 59.43 4.50 o 1 4 6 2.94 4.90 1.70 o 2 4 6 722.22 883.81 8.92 o 1 5 6 378.02 471.89 11.27 o 2 5 6 1213.54 1401.32 19.89 o 3 5 6 25.68 22.06 4.33 o 2 6 6 85.48 61.40 9.04 o 3 6 6 20.28 25.09 5.96 o -5 1 7 536.21 573.35 15.74 o -4 1 7 198.06 206.52 7.12 o -3 1 7 1078.24 1164.39 21.44 o -2 1 7 177.84 165.24 4.26 o -1 1 7 368.96 398.21 13.82 o -6 2 7 615.62 676.06 17.04 o -5 2 7 82.59 92.05 4.43 o -4 2 7 80.95 73.20 8.60 o -3 2 7 749.85 743.12 32.22 o -2 2 7 1165.98 1412.72 17.43 o -1 2 7 1.91 3.87 1.47 o 0 2 7 332.30 281.86 22.68 o -6 3 7 17.32 19.60 5.57 o -5 3 7 253.70 169.62 11.05 o -2 3 7 393.76 437.78 15.30 o -1 3 7 1178.54 1489.89 17.84 o 0 3 7 162.41 159.74 5.21 o 1 3 7 10.45 9.47 2.83 o -1 4 7 267.38 227.00 12.16 o 0 4 7 116.35 106.31 6.64 o 1 4 7 3.56 6.42 2.15 o 2 4 7 11.76 4.08 4.28 o 0 5 7 65.37 67.28 11.52 o 1 5 7 23.57 36.91 5.26 o 2 5 7 118.20 124.04 7.11 o -5 0 8 954.95 867.23 22.51 o -4 0 8 222.04 226.25 7.06 o -3 0 8 94.67 105.19 10.68 o -2 0 8 649.55 389.49 22.48 o -5 1 8 26.85 25.14 4.47 o -4 1 8 60.61 37.30 3.36 o -3 1 8 8.19 9.65 2.64 o -2 1 8 1.69 99.92 25.42 o -1 1 8 15.30 7.53 3.20 o -5 2 8 189.02 163.55 16.98 o -3 2 8 396.16 465.15 14.32 o -2 2 8 55.72 66.13 4.13 o -1 2 8 198.87 210.47 5.87 o -2 3 8 327.41 269.09 20.23 o -1 3 8 0.27 4.49 2.44 o 0 3 8 415.84 361.57 22.00 o -1 4 8 43.43 26.99 5.31 o 0 4 8 567.76 696.92 8.56 o 1 4 8 576.61 594.12 16.38 o 0 5 8 164.99 120.85 13.12 o -3 1 9 388.99 431.34 48.05 o -2 1 9 31.63 14.91 3.15 o -3 2 9 98.86 156.83 15.49 o -2 2 9 21.64 37.25 4.30 o -1 2 9 87.91 28.77 6.76 o -1 3 9 266.71 312.02 13.47 o # AND data_bromochlorofluorocarboxylic_acid_4 _database_code_depnum_ccdc_archive 'CCDC 724002' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromochlorofluorocarboxylic acid ; _chemical_name_common 'bromochlorofluorocarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C2 H Br Cl F O2' _chemical_formula_sum 'C2 H Br Cl F O2' _chemical_formula_weight 191.39 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 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.730(3) _cell_length_b 7.685(3) _cell_length_c 7.997(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.74(2) _cell_angle_gamma 90.00 _cell_volume 472.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1979 _cell_measurement_theta_min 3.69 _cell_measurement_theta_max 24.98 _exptl_crystal_description disc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.460 _exptl_crystal_size_mid 0.450 _exptl_crystal_size_min 0.085 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.689 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 9.154 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.333 _exptl_absorpt_correction_T_max 0.486 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; High-pressure measurement at 1.37 GPa. ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 1370000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1961 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 24.98 _reflns_number_total 277 _reflns_number_gt 259 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed 2.0' _computing_publication_material 'X-seed 2.0' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+3.4947P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 277 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1173 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.4833(3) 0.1425(3) -0.1935(2) 0.0363(9) Uani 0.458(8) 1 d P . . Br2 Br 0.2454(2) -0.0206(2) -0.4835(2) 0.0363(8) Uani 0.542(8) 1 d P . . Cl1 Cl 0.4833(3) 0.1425(3) -0.1935(2) 0.0363(9) Uani 0.542(8) 1 d P . . Cl2 Cl 0.2454(2) -0.0206(2) -0.4835(2) 0.0363(8) Uani 0.458(8) 1 d P . . F1 F 0.2084(10) 0.2856(11) -0.3491(8) 0.038(2) Uani 1 1 d . . . C1 C 0.1358(17) 0.0576(17) -0.1724(15) 0.021(3) Uiso 1 1 d . . . C2 C 0.2597(16) 0.1220(17) -0.2957(14) 0.027(3) Uiso 1 1 d . . . O1 O 0.1906(12) -0.0754(13) -0.0893(10) 0.034(3) Uani 1 1 d . . . O2 O 0.0002(12) 0.1393(12) -0.1635(10) 0.034(2) Uani 1 1 d . . . H1 H 0.1263 -0.0957 -0.0161 0.050 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.029(3) 0.047(3) 0.0322(18) -0.0024(8) 0.002(2) -0.0057(7) Br2 0.040(3) 0.046(3) 0.0234(16) -0.0049(7) 0.0046(19) -0.0009(7) Cl1 0.029(3) 0.047(3) 0.0322(18) -0.0024(8) 0.002(2) -0.0057(7) Cl2 0.040(3) 0.046(3) 0.0234(16) -0.0049(7) 0.0046(19) -0.0009(7) F1 0.052(11) 0.033(11) 0.030(6) 0.003(3) 0.010(7) 0.006(3) O1 0.039(12) 0.039(12) 0.024(6) 0.013(4) 0.013(8) 0.008(4) O2 0.028(12) 0.050(13) 0.025(7) -0.001(4) 0.002(8) 0.003(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br1 C2 1.844(14) . ? Br2 C2 1.854(13) . ? Cl1 C2 1.844(14) . ? Cl2 C2 1.854(13) . ? F1 C2 1.374(14) . ? C1 O2 1.230(14) . ? C1 O1 1.269(14) . ? C1 C2 1.524(15) . ? 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 O2 C1 O1 128.5(9) . . ? O2 C1 C2 117.8(10) . . ? O1 C1 C2 113.7(10) . . ? F1 C2 C1 108.5(9) . . ? F1 C2 Br1 106.8(8) . . ? C1 C2 Br1 111.3(9) . . ? F1 C2 Cl1 106.8(8) . . ? C1 C2 Cl1 111.3(9) . . ? Br1 C2 Cl1 0.00(19) . . ? F1 C2 Br2 107.3(8) . . ? C1 C2 Br2 110.0(10) . . ? Br1 C2 Br2 112.7(6) . . ? Cl1 C2 Br2 112.7(6) . . ? F1 C2 Cl2 107.3(8) . . ? C1 C2 Cl2 110.0(10) . . ? Br1 C2 Cl2 112.7(6) . . ? Cl1 C2 Cl2 112.7(6) . . ? Br2 C2 Cl2 0.00(11) . . ? 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 O2 C1 C2 F1 12.7(18) . . . . ? O1 C1 C2 F1 -166.3(13) . . . . ? O2 C1 C2 Br1 129.8(13) . . . . ? O1 C1 C2 Br1 -49.1(17) . . . . ? O2 C1 C2 Cl1 129.8(13) . . . . ? O1 C1 C2 Cl1 -49.1(17) . . . . ? O2 C1 C2 Br2 -104.5(14) . . . . ? O1 C1 C2 Br2 76.6(15) . . . . ? O2 C1 C2 Cl2 -104.5(14) . . . . ? O1 C1 C2 Cl2 76.6(15) . . . . ? _diffrn_measured_fraction_theta_max 0.335 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.335 _refine_diff_density_max 0.401 _refine_diff_density_min -0.410 _refine_diff_density_rms 0.101 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 1043.83 993.20 18.61 o 2 1 0 23.95 28.40 1.19 o 1 2 0 500.00 488.52 13.18 o 2 2 0 6958.62 6369.83 108.11 o 3 2 0 0.44 5.78 1.48 o 4 2 0 720.02 627.57 22.35 o 2 3 0 322.14 343.35 5.18 o 3 3 0 1492.98 1414.96 28.79 o 4 3 0 203.52 193.49 3.81 o 5 3 0 56.21 47.78 3.82 o 3 4 0 405.75 386.69 14.73 o 4 4 0 93.52 118.21 3.82 o 5 4 0 836.73 902.21 22.10 o 6 4 0 2114.85 2028.68 74.56 o 4 5 0 191.85 171.63 19.57 o 5 5 0 1341.83 1431.28 25.51 o 6 5 0 66.86 74.26 6.18 o 5 6 0 95.12 70.80 16.56 o 6 6 0 33.19 43.09 6.54 o -3 1 1 563.37 535.61 14.15 o -2 1 1 7022.14 6640.69 109.06 o -1 1 1 1887.91 1939.56 42.36 o 0 1 1 1080.81 1098.72 22.53 o 1 1 1 2434.88 2211.21 58.69 o -5 2 1 389.06 391.87 11.36 o -4 2 1 2426.97 2363.87 36.34 o -3 2 1 1246.41 1101.60 23.49 o -2 2 1 5602.56 5389.88 69.05 o 1 2 1 4078.39 3781.93 101.07 o 2 2 1 7847.58 7993.01 200.20 o 3 2 1 671.38 740.24 18.26 o -6 3 1 9.31 -1.30 5.99 o -5 3 1 265.14 284.15 8.25 o -4 3 1 4967.63 4967.05 113.82 o -3 3 1 1149.12 1044.89 29.56 o 1 3 1 330.44 249.08 36.20 o 2 3 1 3037.31 2944.30 52.04 o 3 3 1 11.86 21.49 1.84 o 4 3 1 2784.13 2828.83 37.73 o -6 4 1 130.85 123.60 6.51 o -5 4 1 339.02 356.37 12.53 o -4 4 1 83.91 69.30 3.62 o -3 4 1 70.21 41.26 4.35 o 2 4 1 439.31 378.34 9.11 o 3 4 1 467.83 432.48 31.50 o 4 4 1 919.40 849.34 30.51 o 5 4 1 10.71 5.61 1.81 o -7 5 1 20.47 13.98 4.62 o -6 5 1 166.13 192.91 9.33 o -5 5 1 0.05 2.76 1.68 o 3 5 1 175.57 177.11 10.39 o 4 5 1 291.22 319.40 6.77 o 5 5 1 8.07 8.41 2.54 o 6 5 1 101.60 80.39 9.13 o -6 6 1 22.66 11.81 3.33 o 4 6 1 989.19 872.55 156.57 o 5 6 1 27.26 34.45 5.34 o 6 6 1 149.32 207.27 7.84 o -3 0 2 196.35 206.44 5.17 o -2 0 2 18515.20 18055.39 265.19 o -1 0 2 4502.91 4511.68 105.28 o -4 1 2 1869.41 1835.53 37.82 o -3 1 2 42.12 48.32 1.39 o -2 1 2 6211.37 6385.13 54.03 o -1 1 2 5227.92 5516.44 63.08 o 0 1 2 476.63 566.39 9.89 o 1 1 2 106.35 111.17 8.92 o -5 2 2 527.07 501.35 16.98 o -4 2 2 5849.77 5732.31 102.59 o -3 2 2 204.63 158.57 4.26 o -2 2 2 7764.91 7059.94 452.96 o 0 2 2 9044.95 9568.88 84.95 o 1 2 2 171.27 148.70 2.20 o 2 2 2 1234.51 1142.85 19.71 o -6 3 2 217.15 196.58 14.96 o -5 3 2 629.13 638.41 15.15 o -4 3 2 631.47 729.26 16.19 o -3 3 2 24.32 24.76 1.64 o 1 3 2 1034.64 1049.24 20.65 o 2 3 2 509.85 553.39 10.00 o 3 3 2 840.77 758.25 32.42 o 4 3 2 69.91 47.57 5.36 o -7 4 2 10.30 17.38 5.70 o -6 4 2 125.21 118.53 5.34 o -5 4 2 12.00 12.75 2.12 o -4 4 2 2188.87 1934.77 114.71 o 1 4 2 2247.19 2057.76 69.72 o 2 4 2 135.65 172.47 3.64 o 3 4 2 371.31 385.57 4.37 o 4 4 2 6042.73 6679.58 174.51 o 5 4 2 655.51 471.13 79.60 o -7 5 2 832.31 991.77 32.28 o -6 5 2 1035.38 1096.03 46.67 o -5 5 2 3.63 9.37 3.39 o 2 5 2 260.28 216.63 8.38 o 3 5 2 76.92 70.67 6.43 o 4 5 2 332.96 310.72 5.71 o 5 5 2 11.99 14.00 3.15 o 4 6 2 17.28 26.38 4.36 o 5 6 2 165.69 170.06 8.28 o 6 6 2 524.53 647.73 18.37 o -5 1 3 18.80 24.59 3.84 o -4 1 3 4313.32 4445.69 72.62 o -3 1 3 3792.51 3818.73 57.49 o -2 1 3 24.03 18.52 1.52 o -1 1 3 283.11 346.81 6.37 o 0 1 3 17794.38 18394.50 333.97 o -6 2 3 53.87 37.67 4.06 o -5 2 3 85.15 80.85 3.71 o -4 2 3 71.78 68.34 2.70 o -3 2 3 10.96 15.02 1.77 o -1 2 3 844.98 890.18 19.08 o 0 2 3 3697.16 3938.51 54.15 o 1 2 3 298.69 341.42 6.28 o 2 2 3 10.50 3.32 0.75 o -7 3 3 122.95 88.10 12.90 o -6 3 3 3066.12 3728.14 176.87 o -5 3 3 1231.26 1282.67 12.85 o -4 3 3 197.47 181.27 8.26 o 0 3 3 21.34 23.79 1.85 o 1 3 3 14.52 -6.33 5.43 o 2 3 3 7557.48 7545.84 136.31 o 3 3 3 1187.80 1055.89 32.89 o -7 4 3 5.00 3.78 3.24 o -6 4 3 83.38 72.51 5.44 o -5 4 3 323.64 298.45 17.87 o 1 4 3 1819.93 1824.48 79.16 o 2 4 3 714.03 691.05 19.23 o 3 4 3 426.86 471.00 16.75 o 4 4 3 143.71 101.77 7.69 o -7 5 3 90.75 74.41 10.47 o -6 5 3 822.92 410.64 15.05 o 2 5 3 1704.45 1963.39 82.11 o 3 5 3 38.96 33.37 3.90 o 4 5 3 224.60 234.49 7.00 o 5 5 3 3.17 6.80 5.06 o 3 6 3 3.98 7.78 2.70 o 4 6 3 27.74 33.24 6.41 o 5 6 3 709.75 819.50 20.87 o -4 0 4 1274.69 1278.29 22.69 o -3 0 4 271.38 275.13 4.31 o -2 0 4 3075.85 3089.02 67.19 o -1 0 4 427.98 411.74 9.72 o -5 1 4 383.56 359.71 9.57 o -4 1 4 417.02 422.24 10.76 o -3 1 4 1639.73 1707.97 18.91 o -2 1 4 5225.27 5354.53 131.05 o -1 1 4 284.46 349.53 6.85 o 0 1 4 1775.56 1601.27 64.37 o -6 2 4 599.72 606.82 12.57 o -5 2 4 347.83 366.76 7.41 o -4 2 4 2003.60 2096.73 60.42 o -3 2 4 675.50 612.20 11.08 o -2 2 4 2236.31 2393.29 28.76 o -1 2 4 1111.27 1195.41 15.79 o 0 2 4 3328.59 3463.56 39.77 o 1 2 4 459.35 443.58 8.72 o -7 3 4 322.13 395.08 11.11 o -6 3 4 366.96 390.30 9.26 o -5 3 4 21.98 17.94 2.88 o -4 3 4 206.56 202.08 26.16 o -1 3 4 20.90 24.76 2.10 o 0 3 4 1106.70 1171.95 11.22 o 1 3 4 61.40 55.79 2.31 o 2 3 4 797.64 918.37 10.19 o -7 4 4 336.31 359.69 11.82 o -6 4 4 49.41 37.30 14.89 o 0 4 4 833.61 945.10 7.14 o 1 4 4 22.75 22.89 3.26 o 2 4 4 1098.84 1166.95 21.74 o 3 4 4 812.63 773.31 38.47 o 1 5 4 29.70 20.51 4.22 o 2 5 4 873.64 914.82 25.24 o 3 5 4 944.88 1048.05 21.80 o 4 5 4 889.53 807.01 38.93 o 2 6 4 262.80 201.67 9.62 o 3 6 4 33.70 26.74 3.81 o 4 6 4 506.48 562.98 12.83 o 4 7 4 29.43 34.26 15.51 o -6 1 5 999.35 1083.18 23.23 o -5 1 5 2152.34 2121.57 31.23 o -4 1 5 302.58 324.29 5.65 o -3 1 5 298.15 265.56 6.01 o -2 1 5 7377.19 7655.27 89.86 o -1 1 5 3247.46 3265.55 58.09 o -7 2 5 146.45 100.18 18.89 o -6 2 5 315.13 307.79 7.42 o -5 2 5 220.89 189.19 12.68 o -4 2 5 1392.07 1522.24 34.28 o -3 2 5 49.87 55.86 6.59 o -2 2 5 141.43 145.68 4.12 o -1 2 5 239.06 245.07 3.77 o 0 2 5 700.18 753.73 11.56 o -7 3 5 523.85 579.15 19.28 o -6 3 5 3.07 5.47 3.38 o -5 3 5 9.90 3.69 2.92 o -2 3 5 3.89 6.33 1.99 o -1 3 5 309.07 324.90 4.82 o 0 3 5 4969.24 5385.34 79.92 o 1 3 5 1802.41 1613.12 115.02 o -7 4 5 76.95 54.13 18.88 o -1 4 5 271.63 262.69 17.08 o 0 4 5 486.78 540.03 13.24 o 1 4 5 704.71 713.84 9.49 o 2 4 5 109.35 121.24 5.56 o 1 5 5 499.63 532.67 12.38 o 2 5 5 133.19 128.70 5.32 o 3 5 5 47.04 30.20 4.16 o 2 6 5 61.68 78.16 11.83 o 3 6 5 333.29 327.79 12.58 o 4 6 5 2.41 5.60 7.20 o -5 0 6 15.75 19.56 3.53 o -4 0 6 4220.92 4725.37 63.71 o -3 0 6 2784.19 2921.88 139.15 o -2 0 6 42.15 31.44 7.93 o -6 1 6 130.93 121.73 9.27 o -5 1 6 74.67 69.34 4.87 o -4 1 6 38.56 34.75 2.51 o -3 1 6 754.57 762.68 11.31 o -2 1 6 527.43 541.31 11.77 o -1 1 6 138.14 94.30 12.65 o -7 2 6 12.77 12.03 6.92 o -6 2 6 411.03 392.18 29.27 o -5 2 6 269.84 217.71 26.85 o -3 2 6 349.61 390.11 6.78 o -2 2 6 737.67 872.38 12.01 o -1 2 6 1059.81 1187.76 25.79 o 0 2 6 447.09 408.93 20.34 o -7 3 6 10.23 7.38 6.48 o -6 3 6 5.47 7.89 7.72 o -2 3 6 123.35 135.94 5.24 o -1 3 6 267.21 255.70 5.58 o 0 3 6 272.70 308.84 5.53 o 1 3 6 43.95 23.61 5.12 o -1 4 6 417.99 436.45 9.77 o 0 4 6 109.72 129.95 5.07 o 1 4 6 3.69 8.28 2.87 o 2 4 6 1394.78 1235.07 101.84 o 0 5 6 4.28 5.28 3.62 o 1 5 6 665.16 815.48 16.01 o 2 5 6 1563.21 1657.44 17.04 o 2 6 6 117.31 23.35 9.51 o 3 6 6 22.35 14.20 6.34 o -6 1 7 341.35 399.81 8.99 o -5 1 7 377.39 321.17 15.26 o -4 1 7 634.11 699.72 10.19 o -3 1 7 1112.16 1125.83 34.44 o -2 1 7 379.43 262.84 13.45 o -6 2 7 915.05 725.77 103.34 o -4 2 7 223.75 226.82 9.06 o -3 2 7 1403.85 1379.53 20.61 o -2 2 7 1435.41 1507.54 25.29 o -1 2 7 3.39 2.48 1.67 o -3 3 7 131.43 122.86 13.45 o -2 3 7 1091.76 1215.35 11.55 o -1 3 7 1564.52 1704.57 20.59 o 0 3 7 356.08 320.78 14.20 o -2 4 7 3.19 3.74 3.68 o -1 4 7 423.44 419.32 10.54 o 0 4 7 109.89 82.49 4.70 o 1 4 7 0.49 4.91 3.48 o 0 5 7 125.86 151.89 15.41 o 1 5 7 69.12 57.64 8.71 o -5 0 8 1546.05 1569.91 48.92 o -5 1 8 22.62 21.87 5.84 o -4 1 8 29.68 30.68 6.16 o -3 1 8 36.71 16.28 3.31 o -4 2 8 490.71 560.94 15.47 o -3 2 8 449.61 433.52 33.96 o -2 2 8 179.24 143.16 11.71 o -3 3 8 3.14 5.02 4.59 o -2 3 8 378.08 359.79 9.45 o -1 3 8 3.21 2.19 3.68 o -2 4 8 0.84 6.34 5.33 o -1 4 8 8.53 11.47 4.28 o 0 4 8 1192.29 1040.33 38.96 o -3 2 9 200.96 92.62 15.11 o # AND data_bromochlorofluorocarboxylic_acid_5 _database_code_depnum_ccdc_archive 'CCDC 724003' _audit_creation_method SHELXL-97 _chemical_name_systematic ; bromochlorofluorocarboxylic acid ; _chemical_name_common 'bromochlorofluorocarboxylic acid' _chemical_melting_point ? _chemical_formula_moiety 'C2 H Br Cl F O2' _chemical_formula_sum 'C2 H Br Cl F O2' _chemical_formula_weight 191.39 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 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P bcn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.274(4) _cell_length_b 5.8537(3) _cell_length_c 20.7562(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1855.9(5) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5354 _cell_measurement_theta_min 3.73 _cell_measurement_theta_max 24.98 _exptl_crystal_description disc _exptl_crystal_colour colourless _exptl_crystal_size_max 0.430 _exptl_crystal_size_mid 0.430 _exptl_crystal_size_min 0.085 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.740 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 9.327 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.33 _exptl_absorpt_correction_T_max 0.486 _exptl_absorpt_process_details ; Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Pozna\'n. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 ; _exptl_special_details ; High-pressure measurement at 1.93 GPa. ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 1930000 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7353 _diffrn_reflns_av_R_equivalents 0.1088 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 24.98 _reflns_number_total 439 _reflns_number_gt 407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2004)' _computing_cell_refinement 'CrysAlis (Oxford Diffraction, 2004)' _computing_data_reduction 'CrysAlis (Oxford Diffraction, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-seed 2.0' _computing_publication_material 'X-seed 2.0' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1475P)^2^+59.0716P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 439 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1144 _refine_ls_R_factor_gt 0.1076 _refine_ls_wR_factor_ref 0.2815 _refine_ls_wR_factor_gt 0.2752 _refine_ls_goodness_of_fit_ref 1.241 _refine_ls_restrained_S_all 1.241 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.161(8) -1.035(5) 0.7428(14) 0.037(8) Uiso 1 1 d . . . C2 C 1.084(6) -0.975(4) 0.6801(11) 0.026(7) Uiso 1 1 d . . . O1 O 1.208(5) -0.918(4) 0.7599(11) 0.057(7) Uiso 1 1 d . . . H1 H 1.2176 -0.9426 0.7982 0.086 Uiso 1 1 calc R . . O2 O 1.110(5) -1.203(4) 0.7692(9) 0.11(6) Uani 1 1 d . . . Br1 Br 1.1834(13) -1.0140(9) 0.6151(2) 0.058(16) Uani 0.34 1 d P . . Br2 Br 1.0742(12) -0.6677(9) 0.6839(2) 0.070(15) Uani 0.66 1 d P . . Cl1 Cl 1.1834(13) -1.0140(9) 0.6151(2) 0.058(16) Uani 0.66 1 d P . . Cl2 Cl 1.0742(12) -0.6677(9) 0.6839(2) 0.070(15) Uani 0.34 1 d P . . F1 F 1.045(7) -1.103(6) 0.6618(15) 0.125(12) Uiso 1 1 d . . . C3 C 1.327(7) -1.036(4) 0.8992(11) 0.022(6) Uiso 1 1 d . . . C4 C 1.353(7) -1.149(4) 0.9633(12) 0.027(7) Uiso 1 1 d . . . O3 O 1.405(4) -0.900(3) 0.8848(8) 0.034(5) Uiso 1 1 d . . . H3 H 1.3968 -0.8291 0.8513 0.051 Uiso 1 1 calc R . . O4 O 1.271(4) -1.080(3) 0.8668(8) 0.031(5) Uiso 1 1 d . . . Br3 Br 1.4203(9) -1.4099(6) 0.94708(16) 0.0376(14) Uiso 0.68 1 d P . . Br4 Br 1.3926(12) -0.9829(7) 1.0272(2) 0.0323(15) Uiso 0.32 1 d P . . Cl3 Cl 1.4203(9) -1.4099(6) 0.94708(16) 0.0376(14) Uiso 0.32 1 d P . . Cl4 Cl 1.3926(12) -0.9829(7) 1.0272(2) 0.0323(15) Uiso 0.68 1 d P . . F2 F 1.259(5) -1.232(3) 0.9826(8) 0.048(5) 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 O2 0.2(2) 0.063(13) 0.037(11) 0.033(10) -0.03(2) -0.09(3) Br1 0.09(5) 0.053(3) 0.029(2) -0.0024(19) 0.014(6) 0.001(8) Br2 0.08(5) 0.082(3) 0.045(2) 0.011(2) 0.006(6) 0.034(7) Cl1 0.09(5) 0.053(3) 0.029(2) -0.0024(19) 0.014(6) 0.001(8) Cl2 0.08(5) 0.082(3) 0.045(2) 0.011(2) 0.006(6) 0.034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 1.06(10) . ? C1 O2 1.36(8) . ? C1 C2 1.79(11) . ? C2 F1 1.03(8) . ? C2 Cl2 1.81(3) . ? C2 Br2 1.81(3) . ? C2 Cl1 2.04(7) . ? C2 Br1 2.04(7) . ? C3 O4 1.11(9) . ? C3 O3 1.46(10) . ? C3 C4 1.54(5) . ? C4 F2 1.56(12) . ? C4 Cl4 1.75(4) . ? C4 Br4 1.75(4) . ? C4 Br3 1.87(6) . ? C4 Cl3 1.87(6) . ? 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 O2 136(3) . . ? O1 C1 C2 124(3) . . ? O2 C1 C2 94(7) . . ? F1 C2 Cl2 134(8) . . ? F1 C2 Br2 134(8) . . ? Cl2 C2 Br2 0.0(3) . . ? F1 C2 C1 120(4) . . ? Cl2 C2 C1 103(3) . . ? Br2 C2 C1 103(3) . . ? F1 C2 Cl1 96(5) . . ? Cl2 C2 Cl1 102(3) . . ? Br2 C2 Cl1 102(3) . . ? C1 C2 Cl1 88(5) . . ? F1 C2 Br1 96(5) . . ? Cl2 C2 Br1 102(3) . . ? Br2 C2 Br1 102(3) . . ? C1 C2 Br1 88(5) . . ? Cl1 C2 Br1 0.00(17) . . ? O4 C3 O3 128(3) . . ? O4 C3 C4 129(6) . . ? O3 C3 C4 101(7) . . ? F2 C4 C3 97(7) . . ? F2 C4 Cl4 107(3) . . ? C3 C4 Cl4 120(2) . . ? F2 C4 Br4 107(3) . . ? C3 C4 Br4 120(2) . . ? Cl4 C4 Br4 0.00(18) . . ? F2 C4 Br3 107(2) . . ? C3 C4 Br3 110(3) . . ? Cl4 C4 Br3 114(5) . . ? Br4 C4 Br3 114(5) . . ? F2 C4 Cl3 107(2) . . ? C3 C4 Cl3 110(3) . . ? Cl4 C4 Cl3 114(5) . . ? Br4 C4 Cl3 114(5) . . ? Br3 C4 Cl3 0.0(2) . . ? 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 O1 C1 C2 F1 172(10) . . . . ? O2 C1 C2 F1 -31(9) . . . . ? O1 C1 C2 Cl2 -26(10) . . . . ? O2 C1 C2 Cl2 131(4) . . . . ? O1 C1 C2 Br2 -26(10) . . . . ? O2 C1 C2 Br2 131(4) . . . . ? O1 C1 C2 Cl1 76(8) . . . . ? O2 C1 C2 Cl1 -128(3) . . . . ? O1 C1 C2 Br1 76(8) . . . . ? O2 C1 C2 Br1 -128(3) . . . . ? O4 C3 C4 F2 -28(7) . . . . ? O3 C3 C4 F2 166(3) . . . . ? O4 C3 C4 Cl4 -142(6) . . . . ? O3 C3 C4 Cl4 51(8) . . . . ? O4 C3 C4 Br4 -142(6) . . . . ? O3 C3 C4 Br4 51(8) . . . . ? O4 C3 C4 Br3 83(10) . . . . ? O3 C3 C4 Br3 -83(4) . . . . ? O4 C3 C4 Cl3 83(10) . . . . ? O3 C3 C4 Cl3 -83(4) . . . . ? _diffrn_measured_fraction_theta_max 0.269 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.269 _refine_diff_density_max 0.685 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.179 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_calc _refln_F_squared_meas _refln_F_squared_sigma _refln_observed_status 1 1 0 2983.53 2770.83 93.54 o 0 2 0 97362.42 100958.09 1264.41 o 2 2 0 3535.16 3363.19 86.56 o 1 3 0 2818.17 2072.18 152.13 o 3 3 0 2173.18 1989.63 98.89 o 0 4 0 1093.42 1089.42 69.94 o 2 4 0 9098.91 10488.77 197.77 o 1 5 0 7875.98 10758.85 175.40 o 3 5 0 1490.87 1543.85 144.47 o 0 6 0 102.12 348.66 124.61 o 2 6 0 96.60 284.11 164.68 o 1 1 1 9498.25 9354.21 183.31 o 0 2 1 17149.32 13994.04 211.06 o 1 2 1 7278.92 6507.87 79.96 o 2 2 1 1988.76 1790.55 40.91 o 1 3 1 459.21 817.19 55.35 o 2 3 1 8563.00 7441.44 286.88 o 3 3 1 1421.20 1591.60 65.96 o 0 4 1 5510.41 5081.53 73.42 o 1 4 1 4042.92 4041.02 64.31 o 2 4 1 4837.01 3871.26 77.39 o 3 4 1 7142.11 7663.27 219.79 o 1 5 1 322.77 1116.43 182.36 o 2 5 1 325.59 491.33 66.46 o 3 5 1 128.79 147.90 55.10 o 0 6 1 759.90 1095.52 130.89 o 1 6 1 118.75 201.07 53.44 o 2 6 1 49.98 165.99 79.10 o 3 6 1 8.99 215.07 96.39 o 1 1 2 1627.98 1655.47 21.57 o 0 2 2 25575.55 20772.40 273.06 o 1 2 2 5194.48 6001.37 81.73 o 2 2 2 22466.17 21850.30 394.27 o 1 3 2 15804.13 16028.23 199.38 o 2 3 2 12077.70 11993.04 177.36 o 3 3 2 186.01 759.47 74.81 o 0 4 2 2204.24 1978.84 67.04 o 1 4 2 7777.34 8285.74 296.14 o 2 4 2 1063.63 1087.02 65.70 o 3 4 2 1274.68 1345.86 140.92 o 1 5 2 5643.36 5953.09 79.68 o 2 5 2 895.81 681.38 63.42 o 3 5 2 470.64 512.20 74.53 o 0 6 2 622.01 367.17 84.78 o 1 6 2 4102.63 4488.55 122.70 o 2 6 2 827.02 447.43 90.32 o 3 6 2 2397.07 2590.13 235.38 o 1 1 3 3561.44 3461.04 53.21 o 0 2 3 12570.57 12189.89 219.25 o 1 2 3 769.96 554.19 28.28 o 2 2 3 30725.20 24826.44 432.39 o 1 3 3 5054.02 5697.82 197.60 o 2 3 3 335.35 228.67 24.66 o 3 3 3 547.94 625.73 51.02 o 0 4 3 87.55 146.54 28.34 o 1 4 3 4719.64 4839.25 81.47 o 2 4 3 2732.45 2464.36 60.25 o 3 4 3 10295.97 10359.95 416.99 o 1 5 3 813.08 1197.33 66.24 o 2 5 3 2416.45 2333.82 162.64 o 3 5 3 1.17 142.38 53.13 o 0 6 3 1140.10 1699.55 144.68 o 1 6 3 27.03 164.07 58.35 o 2 6 3 5.95 235.63 71.73 o 3 6 3 699.12 317.41 135.53 o 0 0 4 1422.59 2191.85 110.37 o 1 0 4 24512.64 31304.24 412.80 o 1 1 4 2754.63 2933.29 37.85 o 2 1 4 15374.73 14152.76 142.95 o 0 2 4 8288.05 8425.74 157.25 o 1 2 4 4738.74 3134.15 77.84 o 2 2 4 17483.83 20443.03 467.58 o 1 3 4 9479.23 13467.55 768.11 o 2 3 4 19063.81 18395.55 282.93 o 3 3 4 5406.05 6321.92 267.99 o 0 4 4 160.09 181.09 50.79 o 1 4 4 5606.99 6002.32 87.14 o 2 4 4 1042.58 1496.52 56.45 o 3 4 4 18534.68 20176.24 538.93 o 1 5 4 3107.44 3302.93 82.49 o 2 5 4 2410.32 2566.83 94.74 o 3 5 4 2912.03 2957.27 138.91 o 0 6 4 118.94 188.64 70.01 o 1 6 4 822.14 777.07 87.54 o 2 6 4 360.97 243.66 64.55 o 3 6 4 1985.12 2363.10 213.93 o 1 1 5 2767.59 2644.29 68.89 o 2 1 5 13675.61 13046.38 245.29 o 0 2 5 44759.42 35622.39 563.02 o 1 2 5 970.06 693.94 37.18 o 2 2 5 4754.36 4723.56 255.61 o 3 2 5 2400.32 2430.43 144.82 o 1 3 5 25796.75 24977.38 346.76 o 2 3 5 1149.22 974.86 59.83 o 3 3 5 35.83 146.84 28.14 o 0 4 5 6327.91 5205.69 94.27 o 1 4 5 33.22 306.17 37.44 o 2 4 5 183.85 412.57 43.02 o 3 4 5 2344.41 2777.18 146.80 o 1 5 5 1309.87 1222.26 60.61 o 2 5 5 358.63 256.35 49.68 o 3 5 5 24.86 133.21 56.29 o 0 6 5 534.22 500.17 94.34 o 1 6 5 12.42 165.98 51.89 o 2 6 5 223.36 413.02 84.93 o 3 6 5 309.66 507.14 172.08 o 0 0 6 6999.50 7474.52 146.29 o 1 0 6 4962.56 7821.54 163.91 o 2 0 6 18920.18 21660.41 1119.41 o 1 1 6 20227.85 19480.67 359.83 o 2 1 6 155876.52 162792.08 2711.96 o 0 2 6 10113.68 7144.35 154.85 o 1 2 6 31.80 99.89 12.69 o 2 2 6 3569.67 3403.77 146.69 o 3 2 6 530.54 618.81 69.86 o 1 3 6 1496.02 1908.24 116.37 o 2 3 6 4347.93 3930.87 206.18 o 3 3 6 2329.40 2760.89 203.92 o 0 4 6 198.55 459.45 73.25 o 1 4 6 117.66 69.30 27.54 o 2 4 6 208.74 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