Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _audit_creation_method 'SHELXL-97 plus manual editing' _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Bond, Andrew D.' 'Griffiths, Joanna' 'Hulliger, Jurg' 'Rawson, J.' _publ_contact_author_name 'Dr J Rawson' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UK ; _publ_contact_author_email adb29@cam.ac.uk _publ_contact_author_fax '(01223) 336362' _publ_contact_author_phone '(01223) 336352' _publ_section_title ; Inducing structural polarity in fluorinated organics: X-ray crystal structures of p-XC6F4CN(X=Ci,Br,I) ; data_jr0040a _database_code_CSD 170503 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-iodo-2,3,5,6-fluoro-benzonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 F4 I N' _chemical_formula_sum 'C7 F4 I N' _chemical_formula_weight 300.98 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.252(2) _cell_length_b 8.5160(6) _cell_length_c 6.1817(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 802.92(15) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 12567 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 4.003 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.793 _exptl_absorpt_correction_T_max 0.932 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4924 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 27.46 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 1699 _reflns_number_gt 1298 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0583P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(5) _refine_ls_number_reflns 1699 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.316 _refine_diff_density_min -0.959 _refine_diff_density_rms 0.178 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 I1 I 0.10822(3) 1.59856(5) 0.3993(2) 0.03445(19) Uani 1 1 d . . . F3 F 0.2053(3) 1.2850(5) 1.1119(7) 0.0401(12) Uani 1 1 d . . . F4 F 0.1926(3) 1.5423(5) 0.8619(9) 0.0375(14) Uani 1 1 d . . . F6 F 0.0414(4) 1.2451(6) 0.3353(7) 0.0429(15) Uani 1 1 d . . . F7 F 0.0586(4) 0.9892(5) 0.5833(8) 0.0438(13) Uani 1 1 d . . . N1 N 0.1420(7) 0.8863(8) 1.0990(16) 0.050(2) Uani 1 1 d . . . C1 C 0.1378(6) 0.9947(11) 0.9880(15) 0.036(2) Uani 1 1 d . . . C2 C 0.1312(6) 1.1332(10) 0.8532(13) 0.031(2) Uani 1 1 d . . . C3 C 0.1645(6) 1.2766(9) 0.925(2) 0.032(2) Uani 1 1 d . . . C4 C 0.1569(6) 1.4058(8) 0.7922(14) 0.0292(19) Uani 1 1 d . . . C5 C 0.1157(6) 1.3999(9) 0.5966(16) 0.031(2) Uani 1 1 d . . . C6 C 0.0827(7) 1.2597(10) 0.5272(15) 0.033(2) Uani 1 1 d . . . C7 C 0.0898(6) 1.1258(10) 0.6513(17) 0.036(2) 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 I1 0.0475(3) 0.0257(3) 0.0301(3) 0.0074(3) -0.0005(6) 0.00112(18) F3 0.056(3) 0.036(3) 0.028(3) 0.003(2) -0.006(2) -0.001(2) F4 0.066(3) 0.0260(19) 0.020(4) 0.000(2) -0.005(3) -0.0100(19) F6 0.064(4) 0.036(3) 0.029(4) 0.0065(19) -0.014(2) -0.011(2) F7 0.060(4) 0.026(2) 0.045(3) 0.003(2) -0.001(3) -0.009(2) N1 0.065(6) 0.037(5) 0.048(6) 0.007(4) -0.002(5) 0.005(4) C1 0.043(5) 0.032(4) 0.033(5) 0.011(4) 0.001(4) -0.001(4) C2 0.042(5) 0.031(4) 0.019(7) 0.004(3) 0.005(3) 0.002(3) C3 0.037(4) 0.037(4) 0.023(7) 0.004(5) -0.004(5) 0.001(3) C4 0.042(5) 0.026(4) 0.019(4) -0.002(3) 0.006(4) 0.007(4) C5 0.038(5) 0.031(5) 0.023(5) 0.009(3) 0.006(4) 0.001(3) C6 0.050(7) 0.024(4) 0.025(5) -0.004(4) 0.000(4) -0.001(4) C7 0.045(6) 0.028(4) 0.034(6) -0.002(4) 0.007(4) 0.001(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 I1 C5 2.088(8) . ? F3 C3 1.316(14) . ? F4 C4 1.354(9) . ? F6 C6 1.349(10) . ? F7 C7 1.326(10) . ? N1 C1 1.152(11) . ? C1 C2 1.448(12) . ? C2 C3 1.394(12) . ? C2 C7 1.400(14) . ? C3 C4 1.376(13) . ? C4 C5 1.363(13) . ? C5 C6 1.366(13) . ? C6 C7 1.378(13) . ? 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 N1 C1 C2 178.4(11) . . ? C3 C2 C7 119.1(8) . . ? C3 C2 C1 120.4(9) . . ? C7 C2 C1 120.5(8) . . ? F3 C3 C4 121.3(7) . . ? F3 C3 C2 119.8(9) . . ? C4 C3 C2 118.8(11) . . ? F4 C4 C5 119.9(7) . . ? F4 C4 C3 117.6(9) . . ? C5 C4 C3 122.5(8) . . ? C4 C5 C6 118.7(8) . . ? C4 C5 I1 120.9(6) . . ? C6 C5 I1 120.3(7) . . ? F6 C6 C5 121.9(8) . . ? F6 C6 C7 116.8(8) . . ? C5 C6 C7 121.3(9) . . ? F7 C7 C6 121.4(9) . . ? F7 C7 C2 119.0(8) . . ? C6 C7 C2 119.6(8) . . ? 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 N1 C1 C2 C3 58(40) . . . . ? N1 C1 C2 C7 -120(40) . . . . ? C7 C2 C3 F3 -178.6(9) . . . . ? C1 C2 C3 F3 2.7(14) . . . . ? C7 C2 C3 C4 -1.2(13) . . . . ? C1 C2 C3 C4 -179.9(9) . . . . ? F3 C3 C4 F4 -0.3(14) . . . . ? C2 C3 C4 F4 -177.6(8) . . . . ? F3 C3 C4 C5 179.4(9) . . . . ? C2 C3 C4 C5 2.0(14) . . . . ? F4 C4 C5 C6 178.0(8) . . . . ? C3 C4 C5 C6 -1.7(15) . . . . ? F4 C4 C5 I1 0.9(12) . . . . ? C3 C4 C5 I1 -178.8(7) . . . . ? C4 C5 C6 F6 -179.8(9) . . . . ? I1 C5 C6 F6 -2.7(13) . . . . ? C4 C5 C6 C7 0.4(15) . . . . ? I1 C5 C6 C7 177.6(8) . . . . ? F6 C6 C7 F7 1.0(14) . . . . ? C5 C6 C7 F7 -179.3(9) . . . . ? F6 C6 C7 C2 -179.4(8) . . . . ? C5 C6 C7 C2 0.3(15) . . . . ? C3 C2 C7 F7 179.7(8) . . . . ? C1 C2 C7 F7 -1.7(13) . . . . ? C3 C2 C7 C6 0.1(14) . . . . ? C1 C2 C7 C6 178.7(9) . . . . ? data_jr0041a _database_code_CSD 170504 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromo-2,3,5,6-fluorobenzonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 Br F4 N' _chemical_formula_sum 'C7 Br F4 N' _chemical_formula_weight 253.99 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 '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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 14.6736(12) _cell_length_b 8.2804(5) _cell_length_c 6.1368(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 745.64(10) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3220 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 5.529 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.505 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4047 _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 27.45 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 1647 _reflns_number_gt 1267 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0420P)^2^+0.0744P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.05(2) _refine_ls_number_reflns 1647 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.695 _refine_diff_density_min -0.705 _refine_diff_density_rms 0.121 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 0.10505(3) 0.60254(6) 1.16783(17) 0.03311(19) Uani 1 1 d . . . F3 F 0.0608(2) -0.0055(4) 1.0020(6) 0.0378(9) Uani 1 1 d . . . F4 F 0.0383(2) 0.2583(4) 1.2505(5) 0.0365(9) Uani 1 1 d . . . F6 F 0.1884(2) 0.5711(3) 0.7166(5) 0.0351(10) Uani 1 1 d . . . F7 F 0.2082(2) 0.3088(4) 0.4671(5) 0.0334(8) Uani 1 1 d . . . N1 N 0.1477(4) -0.1043(5) 0.4800(10) 0.0396(13) Uani 1 1 d . . . C1 C 0.1422(4) 0.0056(7) 0.5911(10) 0.0294(14) Uani 1 1 d . . . C2 C 0.1334(4) 0.1452(7) 0.7275(10) 0.0270(14) Uani 1 1 d . . . C3 C 0.0912(4) 0.1378(7) 0.9313(10) 0.0274(14) Uani 1 1 d . . . C4 C 0.0790(4) 0.2720(8) 1.0563(10) 0.0276(14) Uani 1 1 d . . . C5 C 0.1136(3) 0.4206(7) 0.9867(11) 0.0274(13) Uani 1 1 d . . . C6 C 0.1548(4) 0.4306(6) 0.7867(10) 0.0267(14) Uani 1 1 d . . . C7 C 0.1652(3) 0.2962(6) 0.6576(15) 0.0274(11) 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 Br1 0.0416(3) 0.0266(3) 0.0312(3) -0.0087(3) 0.0007(4) 0.0018(2) F3 0.049(2) 0.0239(17) 0.041(2) 0.0030(17) 0.0011(17) -0.0113(16) F4 0.049(2) 0.0345(18) 0.026(2) -0.0040(15) 0.0098(16) -0.0094(17) F6 0.055(2) 0.0224(14) 0.028(3) -0.0019(13) 0.0036(16) -0.0075(15) F7 0.043(2) 0.0345(17) 0.023(2) -0.0036(14) 0.0071(15) -0.0017(17) N1 0.050(3) 0.028(3) 0.040(4) -0.007(2) 0.002(3) 0.003(2) C1 0.033(3) 0.023(3) 0.032(4) 0.001(2) 0.002(3) 0.001(3) C2 0.024(3) 0.023(2) 0.034(4) -0.004(2) -0.003(2) 0.002(2) C3 0.030(3) 0.022(3) 0.031(4) 0.001(2) -0.003(3) -0.005(2) C4 0.028(3) 0.035(3) 0.020(3) 0.003(3) -0.001(3) -0.007(3) C5 0.026(3) 0.024(3) 0.032(4) -0.007(2) -0.007(2) 0.002(3) C6 0.032(3) 0.020(3) 0.028(3) 0.004(2) -0.001(3) -0.007(3) C7 0.026(3) 0.032(2) 0.023(3) -0.003(3) -0.006(4) 0.002(2) _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 C5 1.877(6) . ? F3 C3 1.340(6) . ? F4 C4 1.338(6) . ? F6 C6 1.335(6) . ? F7 C7 1.332(9) . ? N1 C1 1.140(7) . ? C1 C2 1.433(8) . ? C2 C3 1.397(9) . ? C2 C7 1.401(8) . ? C3 C4 1.362(9) . ? C4 C5 1.397(8) . ? C5 C6 1.371(9) . ? C6 C7 1.375(8) . ? 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 N1 C1 C2 178.6(7) . . ? C3 C2 C7 117.4(5) . . ? C3 C2 C1 121.8(5) . . ? C7 C2 C1 120.7(6) . . ? F3 C3 C4 119.8(6) . . ? F3 C3 C2 118.5(5) . . ? C4 C3 C2 121.8(6) . . ? F4 C4 C3 119.4(6) . . ? F4 C4 C5 120.6(6) . . ? C3 C4 C5 119.9(6) . . ? C6 C5 C4 119.2(5) . . ? C6 C5 Br1 120.7(4) . . ? C4 C5 Br1 120.1(5) . . ? F6 C6 C5 120.3(5) . . ? F6 C6 C7 118.6(5) . . ? C5 C6 C7 121.1(6) . . ? F7 C7 C6 119.7(5) . . ? F7 C7 C2 119.8(5) . . ? C6 C7 C2 120.6(7) . . ? 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 N1 C1 C2 C3 102(28) . . . . ? N1 C1 C2 C7 -77(28) . . . . ? C7 C2 C3 F3 -179.6(5) . . . . ? C1 C2 C3 F3 2.0(8) . . . . ? C7 C2 C3 C4 1.6(8) . . . . ? C1 C2 C3 C4 -176.8(5) . . . . ? F3 C3 C4 F4 1.3(8) . . . . ? C2 C3 C4 F4 -179.9(5) . . . . ? F3 C3 C4 C5 177.6(5) . . . . ? C2 C3 C4 C5 -3.6(9) . . . . ? F4 C4 C5 C6 -179.9(5) . . . . ? C3 C4 C5 C6 3.8(9) . . . . ? F4 C4 C5 Br1 1.0(8) . . . . ? C3 C4 C5 Br1 -175.3(4) . . . . ? C4 C5 C6 F6 -180.0(5) . . . . ? Br1 C5 C6 F6 -0.9(8) . . . . ? C4 C5 C6 C7 -2.2(9) . . . . ? Br1 C5 C6 C7 176.9(5) . . . . ? F6 C6 C7 F7 0.0(9) . . . . ? C5 C6 C7 F7 -177.8(5) . . . . ? F6 C6 C7 C2 178.1(5) . . . . ? C5 C6 C7 C2 0.3(9) . . . . ? C3 C2 C7 F7 178.2(5) . . . . ? C1 C2 C7 F7 -3.4(8) . . . . ? C3 C2 C7 C6 0.1(8) . . . . ? C1 C2 C7 C6 178.5(6) . . . . ? data_jr0102 _database_code_CSD 170505 _chemical_name_systematic ? _chemical_name_common '4-chloro-2,3,5,6-fluorobenzonitrile' _chemical_formula_moiety 'C7 Cl F4 N' _chemical_formula_sum 'C7 Cl F4 N' _chemical_formula_weight 209.53 _chemical_melting_point ? 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' '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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.7854(9) _cell_length_b 6.2300(4) _cell_length_c 10.0333(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 736.68(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2615 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method ? _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.534 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_absorpt_correction_T_max 1.128 _exptl_absorpt_correction_T_min 0.959 _exptl_special_details ; Absolute structure determination. ; _diffrn_ambient_temperature 180(2) _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 'Nonius Kappa CCD' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method 'thin-slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 3607 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1464 _reflns_number_observed 1341 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SHELXS-86 (Sheldrick 1986)' _computing_structure_refinement 'SHELXL-93 (Sheldrick 1993)' _computing_publication_material 'SHELXL-93 (Sheldrick 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0604P)^2^+0.0561P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(9) _refine_ls_number_reflns 1462 _refine_ls_number_parameters 118 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_obs 0.0349 _refine_ls_wR_factor_all 0.0980 _refine_ls_wR_factor_obs 0.0936 _refine_ls_goodness_of_fit_all 1.059 _refine_ls_goodness_of_fit_obs 1.066 _refine_ls_restrained_S_all 1.065 _refine_ls_restrained_S_obs 1.066 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.293 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.057 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.21652(6) 0.55105(12) 0.37545(9) 0.0510(2) Uani 1 d . . C1 C 0.4246(2) 0.1435(4) 0.0994(2) 0.0303(5) Uani 1 d . . C2 C 0.3190(2) 0.0763(4) 0.1429(3) 0.0316(5) Uani 1 d . . F2 F 0.27819(14) -0.1147(2) 0.1026(2) 0.0459(4) Uani 1 d . . C3 C 0.2544(2) 0.2009(4) 0.2265(3) 0.0323(5) Uani 1 d . . F3 F 0.15474(13) 0.1273(3) 0.2699(2) 0.0482(4) Uani 1 d . . C4 C 0.2944(2) 0.3982(4) 0.2686(2) 0.0311(5) Uani 1 d . . C5 C 0.3992(2) 0.4690(4) 0.2255(3) 0.0319(5) Uani 1 d . . F5 F 0.43981(13) 0.6569(2) 0.2669(2) 0.0457(4) Uani 1 d . . C6 C 0.4632(2) 0.3441(4) 0.1417(2) 0.0315(5) Uani 1 d . . F6 F 0.56656(13) 0.4166(3) 0.0985(2) 0.0446(4) Uani 1 d . . C7 C 0.4923(3) 0.0093(5) 0.0164(3) 0.0406(6) Uani 1 d . . N1 N 0.5473(3) -0.1008(5) -0.0501(3) 0.0604(8) Uani 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 Cl1 0.0526(4) 0.0550(4) 0.0455(4) -0.0132(4) 0.0078(3) 0.0097(3) C1 0.0346(12) 0.0285(12) 0.0277(11) -0.0001(10) -0.0009(10) 0.0077(9) C2 0.0347(12) 0.0278(12) 0.0322(12) -0.0029(10) -0.0057(10) 0.0007(9) F2 0.0456(9) 0.0313(8) 0.0608(11) -0.0114(7) -0.0042(8) -0.0047(6) C3 0.0254(9) 0.0385(12) 0.0329(11) 0.0003(10) 0.0001(9) 0.0007(10) F3 0.0309(7) 0.0551(10) 0.0586(10) -0.0039(8) 0.0084(8) -0.0072(7) C4 0.0324(12) 0.0328(13) 0.0282(12) -0.0020(10) 0.0004(10) 0.0103(9) C5 0.0358(11) 0.0266(12) 0.0332(11) -0.0025(10) -0.0061(10) -0.0003(9) F5 0.0488(9) 0.0308(8) 0.0574(10) -0.0102(7) -0.0043(8) -0.0059(7) C6 0.0276(11) 0.0352(13) 0.0317(12) 0.0043(10) -0.0009(9) 0.0002(9) F6 0.0295(7) 0.0468(9) 0.0577(10) -0.0023(8) 0.0078(7) -0.0056(6) C7 0.0439(14) 0.0402(14) 0.0377(15) -0.0007(11) 0.0007(12) 0.0091(11) N1 0.069(2) 0.061(2) 0.051(2) -0.0115(14) 0.0157(14) 0.0227(14) _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 Cl1 C4 1.702(2) . ? C1 C2 1.384(4) . ? C1 C6 1.395(4) . ? C1 C7 1.425(4) . ? C2 F2 1.345(3) . ? C2 C3 1.374(4) . ? C3 F3 1.333(3) . ? C3 C4 1.383(4) . ? C4 C5 1.381(4) . ? C5 F5 1.332(3) . ? C5 C6 1.371(4) . ? C6 F6 1.370(3) . ? C7 N1 1.155(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 C2 C1 C6 117.9(2) . . ? C2 C1 C7 120.7(2) . . ? C6 C1 C7 121.4(2) . . ? F2 C2 C3 119.0(2) . . ? F2 C2 C1 119.6(2) . . ? C3 C2 C1 121.3(2) . . ? F3 C3 C2 119.5(2) . . ? F3 C3 C4 120.5(2) . . ? C2 C3 C4 120.0(2) . . ? C5 C4 C3 119.6(2) . . ? C5 C4 Cl1 120.1(2) . . ? C3 C4 Cl1 120.4(2) . . ? F5 C5 C6 119.5(2) . . ? F5 C5 C4 120.3(2) . . ? C6 C5 C4 120.2(2) . . ? F6 C6 C5 119.7(2) . . ? F6 C6 C1 119.2(2) . . ? C5 C6 C1 121.0(2) . . ? N1 C7 C1 179.4(4) . . ?