Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Menahem Kaftory' 'Mark Botoshansky' 'Moshe Kapon' 'Amit Keren' 'Joel S. Miller' 'Yana Sheynin' 'Vitaly Shteiman' 'Boris Tumansky' 'Thomas E. Vos' 'Alexander Zakrassov' _publ_contact_author_name 'Prof Menahem Kaftory' _publ_contact_author_address ; Department of Chemistry Technion -Israel Institute of Technology Haifa 32000 ISRAEL ; _publ_contact_author_email KAFTORY@TX.TECHNION.AC.IL _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Synthesis, Structural, and Magnetic Characterization of Substituted Benzoimidazole-l-yl N,N'-dioxides ; data_dichloro _database_code_depnum_ccdc_archive 'CCDC 228541' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2,6-dichlorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl2 N2 O2' _chemical_formula_sum 'C13 H7 Cl2 N2 O2' _chemical_formula_weight 294.11 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' 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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.580(1) _cell_length_b 8.003(2) _cell_length_c 11.652(2) _cell_angle_alpha 88.60(2) _cell_angle_beta 74.12(2) _cell_angle_gamma 68.84(2) _cell_volume 631.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2871 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 25.32 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.546 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 298 _exptl_absorpt_coefficient_mu 0.511 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9412 _exptl_absorpt_correction_T_max 0.9969 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6069 _diffrn_reflns_av_R_equivalents 0.0885 _diffrn_reflns_av_sigmaI/netI 0.1121 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.32 _reflns_number_total 2218 _reflns_number_gt 1050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0375P)^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_number_reflns 2218 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1348 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _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 Cl1 Cl 0.77104(19) 0.27106(17) 0.23862(11) 0.0763(4) Uani 1 1 d . . . Cl2 Cl 0.02504(19) 0.76065(17) 0.35104(11) 0.0827(5) Uani 1 1 d . . . O1 O 0.3764(5) 0.1617(4) 0.3276(3) 0.0763(10) Uani 1 1 d . . . O2 O 0.2946(4) 0.6208(4) 0.0740(2) 0.0625(8) Uani 1 1 d . . . N1 N 0.3447(5) 0.2526(4) 0.2395(3) 0.0534(9) Uani 1 1 d . . . N2 N 0.3054(5) 0.4720(4) 0.1182(3) 0.0500(9) Uani 1 1 d . . . C1 C 0.3517(6) 0.4199(5) 0.2223(3) 0.0494(10) Uani 1 1 d . . . C2 C 0.2956(6) 0.1947(5) 0.1417(3) 0.0443(10) Uani 1 1 d . . . C3 C 0.2740(6) 0.0370(6) 0.1181(4) 0.0518(11) Uani 1 1 d . . . C4 C 0.2264(7) 0.0237(6) 0.0121(4) 0.0570(12) Uani 1 1 d . . . C5 C 0.2004(7) 0.1617(6) -0.0618(4) 0.0599(12) Uani 1 1 d . . . C6 C 0.2220(7) 0.3191(6) -0.0368(4) 0.0566(12) Uani 1 1 d . . . C7 C 0.2694(6) 0.3318(5) 0.0674(3) 0.0448(10) Uani 1 1 d . . . C8 C 0.4031(7) 0.5253(5) 0.2986(3) 0.0487(10) Uani 1 1 d . . . C9 C 0.2656(7) 0.6895(6) 0.3591(3) 0.0552(11) Uani 1 1 d . . . C10 C 0.3179(9) 0.7968(6) 0.4255(4) 0.0663(14) Uani 1 1 d . . . C11 C 0.5052(9) 0.7377(7) 0.4354(4) 0.0698(15) Uani 1 1 d . . . C12 C 0.6435(9) 0.5760(7) 0.3803(4) 0.0638(13) Uani 1 1 d . . . C13 C 0.5932(7) 0.4707(6) 0.3110(3) 0.0544(11) Uani 1 1 d . . . H3 H 0.309(6) -0.065(5) 0.169(3) 0.063(12) Uiso 1 1 d . . . H4 H 0.206(6) -0.086(5) -0.007(3) 0.067(12) Uiso 1 1 d . . . H5 H 0.166(6) 0.144(5) -0.132(3) 0.059(12) Uiso 1 1 d . . . H6 H 0.200(6) 0.418(5) -0.084(3) 0.063(12) Uiso 1 1 d . . . H10 H 0.203(6) 0.916(5) 0.461(3) 0.065(12) Uiso 1 1 d . . . H11 H 0.547(8) 0.790(7) 0.483(4) 0.12(2) Uiso 1 1 d . . . H12 H 0.785(7) 0.526(5) 0.379(3) 0.072(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0656(9) 0.0749(9) 0.0818(8) -0.0048(6) -0.0223(7) -0.0165(7) Cl2 0.0638(9) 0.0740(9) 0.1008(9) -0.0172(7) -0.0170(7) -0.0177(7) O1 0.126(3) 0.067(2) 0.067(2) 0.0272(17) -0.052(2) -0.055(2) O2 0.080(2) 0.0375(16) 0.0781(19) 0.0125(15) -0.0302(18) -0.0264(16) N1 0.071(3) 0.046(2) 0.055(2) 0.0044(17) -0.0275(19) -0.0276(19) N2 0.054(2) 0.042(2) 0.058(2) 0.0053(17) -0.0188(17) -0.0202(17) C1 0.060(3) 0.043(2) 0.048(2) 0.0021(19) -0.019(2) -0.020(2) C2 0.047(3) 0.037(2) 0.049(2) -0.0011(18) -0.014(2) -0.0160(19) C3 0.050(3) 0.041(2) 0.065(3) 0.003(2) -0.019(2) -0.015(2) C4 0.058(3) 0.051(3) 0.070(3) -0.005(2) -0.024(2) -0.024(2) C5 0.062(3) 0.063(3) 0.061(3) -0.002(2) -0.028(2) -0.022(2) C6 0.062(3) 0.046(3) 0.067(3) 0.007(2) -0.029(2) -0.018(2) C7 0.044(3) 0.036(2) 0.055(2) -0.0015(19) -0.017(2) -0.0118(19) C8 0.064(3) 0.047(2) 0.046(2) 0.0014(19) -0.016(2) -0.032(2) C9 0.067(3) 0.050(3) 0.054(2) -0.001(2) -0.017(2) -0.027(2) C10 0.097(5) 0.045(3) 0.060(3) -0.003(2) -0.020(3) -0.032(3) C11 0.097(5) 0.072(4) 0.067(3) 0.011(3) -0.035(3) -0.053(4) C12 0.073(4) 0.070(4) 0.068(3) 0.016(3) -0.030(3) -0.042(3) C13 0.061(3) 0.060(3) 0.050(2) 0.007(2) -0.013(2) -0.033(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 Cl1 C13 1.723(4) . ? Cl2 C9 1.732(5) . ? O1 N1 1.270(3) . ? O2 N2 1.270(4) . ? N1 C1 1.366(5) . ? N1 C2 1.426(4) . ? N2 C1 1.369(4) . ? N2 C7 1.423(5) . ? C1 C8 1.455(5) . ? C2 C7 1.373(5) . ? C2 C3 1.373(5) . ? C3 C4 1.395(5) . ? C3 H3 1.00(4) . ? C4 C5 1.374(6) . ? C4 H4 0.99(4) . ? C5 C6 1.376(6) . ? C5 H5 0.96(3) . ? C6 C7 1.373(5) . ? C6 H6 0.94(4) . ? C8 C13 1.394(5) . ? C8 C9 1.402(5) . ? C9 C10 1.393(6) . ? C10 C11 1.362(7) . ? C10 H10 1.03(4) . ? C11 C12 1.371(7) . ? C11 H11 0.88(5) . ? C12 C13 1.393(6) . ? C12 H12 0.99(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 N1 C1 126.2(3) . . ? O1 N1 C2 124.8(3) . . ? C1 N1 C2 108.9(3) . . ? O2 N2 C1 126.1(3) . . ? O2 N2 C7 125.3(3) . . ? C1 N2 C7 108.6(3) . . ? N1 C1 N2 108.1(3) . . ? N1 C1 C8 126.9(3) . . ? N2 C1 C8 125.0(4) . . ? C7 C2 C3 122.6(3) . . ? C7 C2 N1 106.9(3) . . ? C3 C2 N1 130.6(3) . . ? C2 C3 C4 115.5(4) . . ? C2 C3 H3 120(2) . . ? C4 C3 H3 123(2) . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4 121(2) . . ? C3 C4 H4 118(2) . . ? C4 C5 C6 122.3(4) . . ? C4 C5 H5 117(2) . . ? C6 C5 H5 121(2) . . ? C7 C6 C5 116.1(4) . . ? C7 C6 H6 120(2) . . ? C5 C6 H6 124(2) . . ? C6 C7 C2 122.0(4) . . ? C6 C7 N2 130.5(4) . . ? C2 C7 N2 107.5(3) . . ? C13 C8 C9 117.2(4) . . ? C13 C8 C1 121.4(4) . . ? C9 C8 C1 121.4(4) . . ? C10 C9 C8 121.6(4) . . ? C10 C9 Cl2 119.2(4) . . ? C8 C9 Cl2 119.2(3) . . ? C11 C10 C9 119.2(5) . . ? C11 C10 H10 128(2) . . ? C9 C10 H10 112(2) . . ? C10 C11 C12 121.3(5) . . ? C10 C11 H11 125(4) . . ? C12 C11 H11 113(4) . . ? C11 C12 C13 119.6(5) . . ? C11 C12 H12 127(2) . . ? C13 C12 H12 114(2) . . ? C12 C13 C8 121.1(4) . . ? C12 C13 Cl1 118.9(4) . . ? C8 C13 Cl1 120.0(3) . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 0.192 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.050 #===END data_difluoro _database_code_depnum_ccdc_archive 'CCDC 228542' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2,6-difluorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 F2 N2 O2' _chemical_formula_sum 'C13 H7 F2 N2 O2' _chemical_formula_weight 261.21 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' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'Pb c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.803(2) _cell_length_b 7.833(1) _cell_length_c 23.664(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2187.8(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2871 _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 25.03 _exptl_crystal_description prism _exptl_crystal_colour blue-green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.586 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.999 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1635 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1813 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1635 _reflns_number_gt 647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0082P)^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_number_reflns 1635 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1986 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0552 _refine_ls_goodness_of_fit_ref 0.819 _refine_ls_restrained_S_all 0.819 _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 F1 F 0.18418(18) 0.2474(2) 0.67899(8) 0.0827(7) Uani 1 1 d . . . F2 F 0.54116(19) -0.0024(3) 0.68611(7) 0.0867(7) Uani 1 1 d . . . O1 O 0.2090(2) -0.0032(3) 0.59065(9) 0.0695(8) Uani 1 1 d . . . O2 O 0.5449(2) 0.2982(3) 0.61197(8) 0.0749(8) Uani 1 1 d . . . N1 N 0.3003(3) 0.0787(4) 0.58048(13) 0.0544(8) Uani 1 1 d . . . N2 N 0.4600(3) 0.2210(4) 0.59034(12) 0.0528(8) Uani 1 1 d . . . C1 C 0.3744(3) 0.1414(4) 0.61909(15) 0.0485(10) Uani 1 1 d . . . C2 C 0.3391(3) 0.1152(4) 0.52523(16) 0.0493(10) Uani 1 1 d . . . C3 C 0.2957(3) 0.0767(4) 0.47360(17) 0.0608(10) Uani 1 1 d . . . H3 H 0.2225 0.0012 0.4692 0.073 Uiso 1 1 d R . . C4 C 0.3562(4) 0.1343(5) 0.42782(15) 0.0708(13) Uani 1 1 d . . . H4 H 0.3273 0.1152 0.3904 0.085 Uiso 1 1 d R . . C5 C 0.4564(4) 0.2235(5) 0.43368(15) 0.0689(12) Uani 1 1 d . . . H5 H 0.4982 0.2609 0.4012 0.083 Uiso 1 1 d R . . C6 C 0.5001(3) 0.2621(4) 0.48591(17) 0.0627(11) Uani 1 1 d . . . H6 H 0.5694 0.3234 0.4922 0.075 Uiso 1 1 d R . . C7 C 0.4389(3) 0.2059(4) 0.53141(15) 0.0500(10) Uani 1 1 d . . . C8 C 0.3646(4) 0.1307(4) 0.67969(15) 0.0512(10) Uani 1 1 d . . . C9 C 0.4487(4) 0.0610(5) 0.71299(19) 0.0619(11) Uani 1 1 d . . . C10 C 0.4433(4) 0.0455(5) 0.77081(17) 0.0782(14) Uani 1 1 d . . . H10 H 0.5057 -0.0007 0.7919 0.094 Uiso 1 1 d R . . C11 C 0.3463(5) 0.1016(6) 0.79675(16) 0.0808(15) Uani 1 1 d . . . H11 H 0.3425 0.0877 0.8370 0.097 Uiso 1 1 d R . . C12 C 0.2593(4) 0.1704(5) 0.7673(2) 0.0757(14) Uani 1 1 d . . . H12 H 0.1909 0.2108 0.7846 0.091 Uiso 1 1 d R . . C13 C 0.2722(4) 0.1801(5) 0.7095(2) 0.0620(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0699(16) 0.0740(18) 0.1043(15) 0.0072(13) 0.0190(13) 0.0121(13) F2 0.0722(17) 0.106(2) 0.0820(13) -0.0104(14) -0.0165(13) 0.0205(14) O1 0.059(2) 0.061(2) 0.0884(17) 0.0090(14) -0.0115(15) -0.0173(16) O2 0.0530(19) 0.086(2) 0.0857(17) -0.0223(15) -0.0072(14) -0.0234(16) N1 0.046(2) 0.044(2) 0.073(2) -0.0002(19) -0.008(2) -0.0016(19) N2 0.042(2) 0.047(2) 0.069(2) -0.0072(18) -0.0044(18) -0.0017(19) C1 0.043(3) 0.044(3) 0.057(3) -0.003(2) -0.006(2) -0.005(2) C2 0.046(3) 0.046(3) 0.055(2) -0.003(2) -0.002(3) 0.006(2) C3 0.053(3) 0.060(3) 0.070(2) -0.010(2) -0.013(2) 0.003(2) C4 0.063(3) 0.087(4) 0.062(3) -0.004(2) -0.008(3) 0.017(3) C5 0.064(3) 0.079(3) 0.063(3) 0.001(2) 0.008(2) 0.014(3) C6 0.051(3) 0.064(3) 0.074(2) -0.009(2) 0.006(3) 0.005(2) C7 0.049(3) 0.048(3) 0.053(3) -0.006(2) -0.005(2) 0.011(2) C8 0.050(3) 0.040(3) 0.064(3) -0.007(2) 0.000(3) 0.003(2) C9 0.055(3) 0.058(3) 0.072(3) -0.016(2) 0.005(3) -0.001(3) C10 0.089(4) 0.077(4) 0.068(3) -0.003(3) -0.019(3) -0.006(3) C11 0.119(5) 0.067(4) 0.057(3) -0.005(2) 0.003(3) -0.032(3) C12 0.096(4) 0.060(4) 0.072(3) -0.003(3) 0.021(3) -0.011(3) C13 0.056(4) 0.046(3) 0.084(3) 0.002(2) -0.006(3) 0.000(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 F1 C13 1.371(4) . ? F2 C9 1.357(4) . ? O1 N1 1.277(3) . ? O2 N2 1.278(3) . ? N1 C1 1.357(4) . ? N1 C2 1.415(4) . ? N2 C1 1.369(4) . ? N2 C7 1.421(4) . ? C1 C8 1.441(4) . ? C2 C3 1.359(4) . ? C2 C7 1.383(4) . ? C3 C4 1.374(4) . ? C3 H3 1.0517 . ? C4 C5 1.380(4) . ? C4 H4 0.9599 . ? C5 C6 1.373(4) . ? C5 H5 0.9601 . ? C6 C7 1.369(4) . ? C6 H6 0.9599 . ? C8 C13 1.356(4) . ? C8 C9 1.380(4) . ? C9 C10 1.375(4) . ? C10 C11 1.372(5) . ? C10 H10 0.9601 . ? C11 C12 1.353(5) . ? C11 H11 0.9600 . ? C12 C13 1.377(4) . ? C12 H12 0.9601 . ? 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 N1 C1 126.8(3) . . ? O1 N1 C2 123.3(3) . . ? C1 N1 C2 109.9(3) . . ? O2 N2 C1 126.6(3) . . ? O2 N2 C7 124.7(3) . . ? C1 N2 C7 108.7(3) . . ? N1 C1 N2 107.8(3) . . ? N1 C1 C8 126.6(4) . . ? N2 C1 C8 125.5(3) . . ? C3 C2 C7 122.0(3) . . ? C3 C2 N1 131.6(4) . . ? C7 C2 N1 106.4(3) . . ? C2 C3 C4 116.1(3) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 122.2 . . ? C3 C4 C5 122.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 118.4 . . ? C6 C5 C4 121.6(3) . . ? C6 C5 H5 117.5 . . ? C4 C5 H5 120.9 . . ? C7 C6 C5 116.0(3) . . ? C7 C6 H6 119.2 . . ? C5 C6 H6 124.8 . . ? C6 C7 C2 122.1(3) . . ? C6 C7 N2 130.7(4) . . ? C2 C7 N2 107.2(3) . . ? C13 C8 C9 113.2(4) . . ? C13 C8 C1 124.5(4) . . ? C9 C8 C1 122.2(4) . . ? F2 C9 C10 118.1(4) . . ? F2 C9 C8 117.1(4) . . ? C10 C9 C8 124.7(4) . . ? C9 C10 C11 117.1(4) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 121.9 . . ? C12 C11 C10 122.0(4) . . ? C12 C11 H11 121.4 . . ? C10 C11 H11 116.6 . . ? C11 C12 C13 116.7(4) . . ? C11 C12 H12 123.3 . . ? C13 C12 H12 119.9 . . ? C8 C13 F1 116.4(4) . . ? C8 C13 C12 126.2(4) . . ? F1 C13 C12 117.5(4) . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.847 _refine_diff_density_max 0.141 _refine_diff_density_min -0.162 _refine_diff_density_rms 0.037 #===END data_difl(b) _database_code_depnum_ccdc_archive 'CCDC 228543' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2,6-difluorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 F2 N2 O2' _chemical_formula_sum 'C13 H7 F2 N2 O2' _chemical_formula_weight 261.21 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' 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' O O 0.0106 0.0060 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.942(1) _cell_length_b 21.265(3) _cell_length_c 8.886(1) _cell_angle_alpha 90.00 _cell_angle_beta 121.30(2) _cell_angle_gamma 90.00 _cell_volume 1120.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2003 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 25.05 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 532 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1972 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0899 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1972 _reflns_number_gt 1005 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0619P)^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 SHELXL _refine_ls_extinction_coef 0.023(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1972 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1253 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1418 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 F1 F 0.9925(3) -0.11035(11) 1.0320(3) 0.0749(7) Uani 1 1 d . . . F2 F 0.2608(4) -0.17119(10) 0.8689(3) 0.0789(8) Uani 1 1 d . . . O1 O 0.7233(4) -0.00190(11) 1.0121(3) 0.0584(7) Uani 1 1 d . . . O2 O 0.2834(4) -0.14121(11) 0.5604(3) 0.0672(8) Uani 1 1 d . . . N1 N 0.5805(4) -0.02435(12) 0.8609(3) 0.0449(7) Uani 1 1 d . . . N2 N 0.3695(4) -0.09039(12) 0.6468(4) 0.0488(8) Uani 1 1 d . . . C1 C 0.5286(5) -0.08652(14) 0.8205(4) 0.0449(8) Uani 1 1 d . . . C2 C 0.4453(6) 0.01176(14) 0.7079(4) 0.0452(8) Uani 1 1 d . . . C3 C 0.4321(6) 0.07613(15) 0.6835(5) 0.0543(10) Uani 1 1 d . . . H3 H 0.5283 0.1034 0.7801 0.065 Uiso 1 1 d R . . C4 C 0.2743(7) 0.09619(18) 0.5149(5) 0.0637(11) Uani 1 1 d . . . H4 H 0.2535 0.1403 0.4883 0.076 Uiso 1 1 d R . . C5 C 0.1410(6) 0.05470(18) 0.3780(5) 0.0582(10) Uani 1 1 d . . . H5 H 0.0365 0.0718 0.2639 0.070 Uiso 1 1 d R . . C6 C 0.1586(6) -0.00968(16) 0.4049(4) 0.0527(9) Uani 1 1 d . . . H6 H 0.0742 -0.0401 0.3140 0.063 Uiso 1 1 d R . . C7 C 0.3134(5) -0.02913(14) 0.5737(4) 0.0448(9) Uani 1 1 d . . . C8 C 0.6216(6) -0.13841(15) 0.9434(4) 0.0469(9) Uani 1 1 d . . . C9 C 0.4869(7) -0.18059(17) 0.9666(5) 0.0603(10) Uani 1 1 d . . . C10 C 0.5678(8) -0.22921(17) 1.0839(6) 0.0743(13) Uani 1 1 d . . . H10 H 0.4669 -0.2580 1.0919 0.089 Uiso 1 1 d R . . C11 C 0.7999(9) -0.23603(19) 1.1885(6) 0.0807(14) Uani 1 1 d . . . H11 H 0.8593 -0.2692 1.2742 0.097 Uiso 1 1 d R . . C12 C 0.9415(7) -0.19631(19) 1.1725(5) 0.0724(13) Uani 1 1 d . . . H12 H 1.1025 -0.2004 1.2429 0.087 Uiso 1 1 d R . . C13 C 0.8511(6) -0.14883(17) 1.0504(5) 0.0563(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0526(13) 0.0912(16) 0.0710(16) 0.0138(12) 0.0252(12) 0.0041(11) F2 0.0603(15) 0.0701(15) 0.0997(18) 0.0037(13) 0.0370(13) -0.0110(11) O1 0.0521(15) 0.0662(16) 0.0421(14) -0.0093(12) 0.0141(12) -0.0099(12) O2 0.0731(18) 0.0500(15) 0.0590(16) -0.0188(12) 0.0205(14) -0.0057(13) N1 0.0430(16) 0.0481(16) 0.0405(16) -0.0012(13) 0.0195(14) -0.0018(13) N2 0.0489(17) 0.0450(16) 0.0444(16) -0.0016(14) 0.0186(14) 0.0036(14) C1 0.0428(19) 0.047(2) 0.0397(19) 0.0026(16) 0.0179(16) 0.0034(16) C2 0.0452(19) 0.049(2) 0.0412(18) 0.0023(16) 0.0225(16) 0.0016(16) C3 0.063(2) 0.049(2) 0.055(2) -0.0009(17) 0.034(2) -0.0011(18) C4 0.076(3) 0.055(2) 0.072(3) 0.017(2) 0.046(2) 0.014(2) C5 0.056(2) 0.072(3) 0.049(2) 0.016(2) 0.0288(19) 0.014(2) C6 0.050(2) 0.064(2) 0.040(2) 0.0004(16) 0.0197(18) 0.0053(17) C7 0.046(2) 0.0485(19) 0.045(2) -0.0034(16) 0.0274(17) 0.0035(16) C8 0.050(2) 0.0454(19) 0.0402(19) 0.0016(15) 0.0195(17) 0.0041(16) C9 0.061(3) 0.053(2) 0.064(3) -0.0011(19) 0.030(2) -0.003(2) C10 0.099(4) 0.049(2) 0.076(3) 0.003(2) 0.046(3) -0.009(2) C11 0.108(4) 0.054(2) 0.060(3) 0.011(2) 0.030(3) 0.008(3) C12 0.075(3) 0.067(3) 0.053(3) 0.004(2) 0.018(2) 0.011(2) C13 0.053(2) 0.057(2) 0.048(2) 0.0052(17) 0.0190(19) 0.0027(19) _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 F1 C13 1.351(4) . ? F2 C9 1.357(4) . ? O1 N1 1.277(3) . ? O2 N2 1.280(3) . ? N1 C1 1.368(4) . ? N1 C2 1.412(4) . ? N2 C1 1.355(4) . ? N2 C7 1.417(4) . ? C1 C8 1.447(4) . ? C2 C7 1.372(4) . ? C2 C3 1.381(4) . ? C3 C4 1.387(5) . ? C3 H3 0.9601 . ? C4 C5 1.394(5) . ? C4 H4 0.9600 . ? C5 C6 1.384(5) . ? C5 H5 0.9600 . ? C6 C7 1.379(4) . ? C6 H6 0.9600 . ? C8 C13 1.385(4) . ? C8 C9 1.387(5) . ? C9 C10 1.365(5) . ? C10 C11 1.388(6) . ? C10 H10 0.9600 . ? C11 C12 1.359(6) . ? C11 H11 0.9601 . ? C12 C13 1.372(5) . ? C12 H12 0.9600 . ? 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 N1 C1 126.3(3) . . ? O1 N1 C2 125.0(3) . . ? C1 N1 C2 108.6(2) . . ? O2 N2 C1 125.8(3) . . ? O2 N2 C7 124.7(3) . . ? C1 N2 C7 109.5(3) . . ? N2 C1 N1 107.8(3) . . ? N2 C1 C8 126.4(3) . . ? N1 C1 C8 125.8(3) . . ? C7 C2 C3 122.1(3) . . ? C7 C2 N1 107.6(3) . . ? C3 C2 N1 130.3(3) . . ? C2 C3 C4 115.1(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 124.9 . . ? C3 C4 C5 122.8(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 117.2 . . ? C6 C5 C4 121.1(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 118.5 . . ? C7 C6 C5 115.7(3) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 124.1 . . ? C2 C7 C6 123.1(3) . . ? C2 C7 N2 106.5(3) . . ? C6 C7 N2 130.4(3) . . ? C13 C8 C9 114.7(3) . . ? C13 C8 C1 122.9(3) . . ? C9 C8 C1 122.3(3) . . ? F2 C9 C10 118.7(4) . . ? F2 C9 C8 117.1(3) . . ? C10 C9 C8 124.2(4) . . ? C9 C10 C11 117.7(4) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 121.4 . . ? C12 C11 C10 121.1(4) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 118.6 . . ? C11 C12 C13 118.8(4) . . ? C11 C12 H12 122.5 . . ? C13 C12 H12 118.7 . . ? F1 C13 C12 118.6(4) . . ? F1 C13 C8 118.0(3) . . ? C12 C13 C8 123.5(4) . . ? 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 N2 C1 N1 178.2(3) . . . . ? C7 N2 C1 N1 -1.2(4) . . . . ? O2 N2 C1 C8 -4.0(6) . . . . ? C7 N2 C1 C8 176.6(3) . . . . ? O1 N1 C1 N2 179.9(3) . . . . ? C2 N1 C1 N2 1.3(4) . . . . ? O1 N1 C1 C8 2.0(6) . . . . ? C2 N1 C1 C8 -176.6(3) . . . . ? O1 N1 C2 C7 -179.5(3) . . . . ? C1 N1 C2 C7 -0.9(4) . . . . ? O1 N1 C2 C3 -0.4(6) . . . . ? C1 N1 C2 C3 178.2(4) . . . . ? C7 C2 C3 C4 0.8(5) . . . . ? N1 C2 C3 C4 -178.1(4) . . . . ? C2 C3 C4 C5 -1.2(6) . . . . ? C3 C4 C5 C6 0.7(6) . . . . ? C4 C5 C6 C7 0.3(5) . . . . ? C3 C2 C7 C6 0.1(5) . . . . ? N1 C2 C7 C6 179.3(3) . . . . ? C3 C2 C7 N2 -179.1(3) . . . . ? N1 C2 C7 N2 0.1(4) . . . . ? C5 C6 C7 C2 -0.7(5) . . . . ? C5 C6 C7 N2 178.2(3) . . . . ? O2 N2 C7 C2 -178.7(3) . . . . ? C1 N2 C7 C2 0.7(4) . . . . ? O2 N2 C7 C6 2.2(6) . . . . ? C1 N2 C7 C6 -178.4(3) . . . . ? N2 C1 C8 C13 128.0(4) . . . . ? N1 C1 C8 C13 -54.5(5) . . . . ? N2 C1 C8 C9 -53.9(5) . . . . ? N1 C1 C8 C9 123.6(4) . . . . ? C13 C8 C9 F2 177.9(3) . . . . ? C1 C8 C9 F2 -0.3(5) . . . . ? C13 C8 C9 C10 -0.2(6) . . . . ? C1 C8 C9 C10 -178.4(4) . . . . ? F2 C9 C10 C11 -176.9(3) . . . . ? C8 C9 C10 C11 1.2(6) . . . . ? C9 C10 C11 C12 -1.1(6) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 F1 -178.5(4) . . . . ? C11 C12 C13 C8 1.0(6) . . . . ? C9 C8 C13 F1 178.5(3) . . . . ? C1 C8 C13 F1 -3.2(5) . . . . ? C9 C8 C13 C12 -1.0(5) . . . . ? C1 C8 C13 C12 177.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.201 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.046 #===END data_clf(a) _database_code_depnum_ccdc_archive 'CCDC 228544' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2-chloro,6-fluorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl F N2 O2' _chemical_formula_sum 'C13 H7 Cl F N2 O2' _chemical_formula_weight 277.66 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' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 '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' F F 0.0171 0.0103 '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 10.370(2) _cell_length_b 15.787(3) _cell_length_c 7.790(1) _cell_angle_alpha 90.00 _cell_angle_beta 109.68(3) _cell_angle_gamma 90.00 _cell_volume 1200.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9048 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 25.01 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.536 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.329 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8742 _exptl_absorpt_correction_T_max 0.9902 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9048 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2106 _reflns_number_gt 1524 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.1345P)^2^+0.8565P] 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_number_reflns 2106 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1158 _refine_ls_R_factor_gt 0.0898 _refine_ls_wR_factor_ref 0.2320 _refine_ls_wR_factor_gt 0.2183 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 Cl1 Cl 0.19238(16) 0.02777(9) 1.23145(16) 0.0654(5) Uani 1 1 d . . . F1 F 0.2080(3) -0.02310(18) 0.6013(3) 0.0595(8) Uani 1 1 d . . . O1 O 0.1184(3) -0.1721(2) 0.7775(4) 0.0550(9) Uani 1 1 d . . . O2 O 0.4789(4) -0.0223(2) 1.1762(4) 0.0574(9) Uani 1 1 d . . . N1 N 0.2327(3) -0.1536(2) 0.8981(4) 0.0396(8) Uani 1 1 d . . . N2 N 0.4045(4) -0.0823(2) 1.0888(4) 0.0415(9) Uani 1 1 d . . . C1 C 0.2772(4) -0.0748(3) 0.9581(5) 0.0372(9) Uani 1 1 d . . . C2 C 0.3331(4) -0.2134(3) 0.9939(5) 0.0413(10) Uani 1 1 d . . . C3 C 0.3321(5) -0.3009(3) 0.9859(7) 0.0558(12) Uani 1 1 d . . . H3 H 0.2589 -0.3309 0.9068 0.067 Uiso 1 1 calc R . . C4 C 0.4461(6) -0.3408(3) 1.1021(9) 0.0702(16) Uani 1 1 d . . . H4 H 0.4507 -0.3996 1.1014 0.084 Uiso 1 1 calc R . . C5 C 0.5523(6) -0.2962(4) 1.2183(8) 0.0744(17) Uani 1 1 d . . . H5 H 0.6269 -0.3261 1.2944 0.089 Uiso 1 1 calc R . . C6 C 0.5550(5) -0.2085(4) 1.2290(7) 0.0607(13) Uani 1 1 d . . . H6 H 0.6282 -0.1787 1.3084 0.073 Uiso 1 1 calc R . . C7 C 0.4400(4) -0.1691(3) 1.1118(6) 0.0448(10) Uani 1 1 d . . . C8 C 0.2029(4) 0.0033(3) 0.8946(5) 0.0381(9) Uani 1 1 d . . . C9 C 0.1679(5) 0.0274(3) 0.7140(6) 0.0467(11) Uani 1 1 d . . . C10 C 0.0954(5) 0.0986(3) 0.6424(7) 0.0555(13) Uani 1 1 d . . . H10 H 0.0726 0.1116 0.5193 0.067 Uiso 1 1 calc R . . C11 C 0.0575(5) 0.1502(3) 0.7578(8) 0.0634(14) Uani 1 1 d . . . H11 H 0.0101 0.1999 0.7125 0.076 Uiso 1 1 calc R . . C12 C 0.0879(5) 0.1305(3) 0.9409(8) 0.0610(14) Uani 1 1 d . . . H12 H 0.0604 0.1660 1.0174 0.073 Uiso 1 1 calc R . . C13 C 0.1610(5) 0.0557(3) 1.0082(6) 0.0469(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 Cl1 0.0770(10) 0.0703(10) 0.0564(8) -0.0078(6) 0.0322(6) -0.0088(7) F1 0.071(2) 0.065(2) 0.0403(14) -0.0018(12) 0.0164(13) 0.0072(14) O1 0.0397(18) 0.0448(19) 0.0639(19) -0.0035(14) -0.0045(14) -0.0077(14) O2 0.051(2) 0.050(2) 0.0589(19) -0.0095(15) 0.0028(15) -0.0138(16) N1 0.037(2) 0.0288(19) 0.0482(19) 0.0029(14) 0.0079(15) -0.0003(15) N2 0.0355(19) 0.041(2) 0.0421(18) -0.0005(15) 0.0047(14) -0.0036(16) C1 0.036(2) 0.032(2) 0.040(2) 0.0008(16) 0.0080(16) -0.0025(17) C2 0.037(2) 0.033(2) 0.053(2) 0.0099(18) 0.0140(18) 0.0032(18) C3 0.055(3) 0.036(3) 0.076(3) 0.008(2) 0.022(2) 0.006(2) C4 0.072(4) 0.041(3) 0.103(4) 0.025(3) 0.035(3) 0.020(3) C5 0.060(4) 0.073(4) 0.088(4) 0.031(3) 0.021(3) 0.029(3) C6 0.042(3) 0.066(4) 0.066(3) 0.015(2) 0.007(2) 0.011(2) C7 0.040(2) 0.044(3) 0.050(2) 0.0093(19) 0.0140(19) 0.005(2) C8 0.029(2) 0.033(2) 0.048(2) 0.0009(17) 0.0069(17) -0.0046(17) C9 0.042(3) 0.038(3) 0.056(3) 0.0032(19) 0.0107(19) -0.0056(19) C10 0.047(3) 0.046(3) 0.063(3) 0.014(2) 0.004(2) 0.000(2) C11 0.043(3) 0.043(3) 0.096(4) 0.013(3) 0.012(3) 0.006(2) C12 0.051(3) 0.040(3) 0.097(4) -0.014(3) 0.031(3) -0.001(2) C13 0.043(2) 0.038(3) 0.062(3) -0.0061(19) 0.020(2) -0.011(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 Cl1 C13 1.716(5) . ? F1 C9 1.351(5) . ? O1 N1 1.274(4) . ? O2 N2 1.265(4) . ? N1 C1 1.354(5) . ? N1 C2 1.418(5) . ? N2 C1 1.374(5) . ? N2 C7 1.416(6) . ? C1 C8 1.450(6) . ? C2 C7 1.370(6) . ? C2 C3 1.382(7) . ? C3 C4 1.376(8) . ? C3 H3 0.9300 . ? C4 C5 1.362(9) . ? C4 H4 0.9300 . ? C5 C6 1.386(8) . ? C5 H5 0.9300 . ? C6 C7 1.381(6) . ? C6 H6 0.9300 . ? C8 C9 1.382(6) . ? C8 C13 1.385(6) . ? C9 C10 1.364(7) . ? C10 C11 1.364(8) . ? C10 H10 0.9300 . ? C11 C12 1.389(8) . ? C11 H11 0.9300 . ? C12 C13 1.405(7) . ? C12 H12 0.9300 . ? 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 N1 C1 126.1(3) . . ? O1 N1 C2 124.9(3) . . ? C1 N1 C2 109.0(3) . . ? O2 N2 C1 126.5(4) . . ? O2 N2 C7 124.8(4) . . ? C1 N2 C7 108.7(3) . . ? N1 C1 N2 107.9(3) . . ? N1 C1 C8 125.7(3) . . ? N2 C1 C8 126.4(3) . . ? C7 C2 C3 122.2(4) . . ? C7 C2 N1 107.3(4) . . ? C3 C2 N1 130.4(4) . . ? C4 C3 C2 115.8(5) . . ? C4 C3 H3 122.1 . . ? C2 C3 H3 122.1 . . ? C5 C4 C3 121.6(5) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 123.4(5) . . ? C4 C5 H5 118.3 . . ? C6 C5 H5 118.3 . . ? C7 C6 C5 114.5(5) . . ? C7 C6 H6 122.8 . . ? C5 C6 H6 122.8 . . ? C2 C7 C6 122.4(5) . . ? C2 C7 N2 107.0(4) . . ? C6 C7 N2 130.5(4) . . ? C9 C8 C13 117.1(4) . . ? C9 C8 C1 120.6(4) . . ? C13 C8 C1 122.4(4) . . ? F1 C9 C10 118.0(4) . . ? F1 C9 C8 117.8(4) . . ? C10 C9 C8 124.2(4) . . ? C9 C10 C11 117.7(5) . . ? C9 C10 H10 121.2 . . ? C11 C10 H10 121.2 . . ? C10 C11 C12 121.8(5) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C13 118.6(5) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C8 C13 C12 120.6(4) . . ? C8 C13 Cl1 120.1(4) . . ? C12 C13 Cl1 119.2(4) . . ? 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 N1 C1 N2 179.5(4) . . . . ? C2 N1 C1 N2 0.7(4) . . . . ? O1 N1 C1 C8 -0.6(6) . . . . ? C2 N1 C1 C8 -179.5(4) . . . . ? O2 N2 C1 N1 179.8(4) . . . . ? C7 N2 C1 N1 -0.5(4) . . . . ? O2 N2 C1 C8 -0.1(7) . . . . ? C7 N2 C1 C8 179.7(4) . . . . ? O1 N1 C2 C7 -179.5(4) . . . . ? C1 N1 C2 C7 -0.6(4) . . . . ? O1 N1 C2 C3 -1.8(7) . . . . ? C1 N1 C2 C3 177.0(4) . . . . ? C7 C2 C3 C4 -0.9(7) . . . . ? N1 C2 C3 C4 -178.3(5) . . . . ? C2 C3 C4 C5 0.5(8) . . . . ? C3 C4 C5 C6 -0.2(9) . . . . ? C4 C5 C6 C7 0.3(8) . . . . ? C3 C2 C7 C6 1.0(7) . . . . ? N1 C2 C7 C6 178.9(4) . . . . ? C3 C2 C7 N2 -177.6(4) . . . . ? N1 C2 C7 N2 0.3(4) . . . . ? C5 C6 C7 C2 -0.6(7) . . . . ? C5 C6 C7 N2 177.6(4) . . . . ? O2 N2 C7 C2 179.8(4) . . . . ? C1 N2 C7 C2 0.1(5) . . . . ? O2 N2 C7 C6 1.4(7) . . . . ? C1 N2 C7 C6 -178.4(5) . . . . ? N1 C1 C8 C9 -61.1(6) . . . . ? N2 C1 C8 C9 118.8(5) . . . . ? N1 C1 C8 C13 117.2(5) . . . . ? N2 C1 C8 C13 -62.9(6) . . . . ? C13 C8 C9 F1 -180.0(4) . . . . ? C1 C8 C9 F1 -1.6(6) . . . . ? C13 C8 C9 C10 0.0(6) . . . . ? C1 C8 C9 C10 178.3(4) . . . . ? F1 C9 C10 C11 -178.7(4) . . . . ? C8 C9 C10 C11 1.3(7) . . . . ? C9 C10 C11 C12 -1.6(8) . . . . ? C10 C11 C12 C13 0.7(8) . . . . ? C9 C8 C13 C12 -0.9(6) . . . . ? C1 C8 C13 C12 -179.3(4) . . . . ? C9 C8 C13 Cl1 176.6(3) . . . . ? C1 C8 C13 Cl1 -1.8(6) . . . . ? C11 C12 C13 C8 0.6(7) . . . . ? C11 C12 C13 Cl1 -176.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.781 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.100 #===END data_clf(b) _database_code_depnum_ccdc_archive 'CCDC 228545' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2-chloro,6-fluorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H7 Cl F N2 O2' _chemical_formula_sum 'C13 H7 Cl F N2 O2' _chemical_formula_weight 277.66 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' O O 0.0106 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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/n' _symmetry_space_group_name_Hall '-P 2ybn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.396(1) _cell_length_b 20.665(3) _cell_length_c 8.180(1) _cell_angle_alpha 90.00 _cell_angle_beta 105.38(2) _cell_angle_gamma 90.00 _cell_volume 1205.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 198 _cell_measurement_theta_min 1.97 _cell_measurement_theta_max 24.34 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.319 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9389 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1310 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1513 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 24.34 _reflns_number_total 1310 _reflns_number_gt 501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0712P)^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_number_reflns 1310 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1885 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_restrained_S_all 0.848 _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 Cl1 Cl 0.5233(4) 0.10493(14) 1.0329(3) 0.1304(12) Uani 1 1 d . . . F1 F 1.1071(7) 0.1705(3) 0.8651(7) 0.113(2) Uani 1 1 d . . . O1 O 0.7795(9) 0.1473(3) 0.5802(8) 0.124(3) Uani 1 1 d . . . O2 O 0.8045(7) -0.0037(3) 1.0046(8) 0.0962(19) Uani 1 1 d . . . N1 N 0.7819(9) 0.0933(4) 0.6535(11) 0.092(2) Uani 1 1 d . . . N2 N 0.7904(9) 0.0222(4) 0.8603(12) 0.085(2) Uani 1 1 d . . . C1 C 0.7990(11) 0.0870(5) 0.8249(14) 0.081(3) Uani 1 1 d . . . C2 C 0.7675(11) 0.0310(5) 0.5832(16) 0.083(3) Uani 1 1 d . . . C3 C 0.7523(12) 0.0146(6) 0.4167(14) 0.103(3) Uani 1 1 d . . . H3 H 0.7452 0.0454 0.3324 0.124 Uiso 1 1 calc R . . C4 C 0.7483(12) -0.0504(7) 0.3848(14) 0.108(3) Uani 1 1 d . . . H4 H 0.7406 -0.0644 0.2751 0.129 Uiso 1 1 calc R . . C5 C 0.7551(13) -0.0954(6) 0.5082(18) 0.115(3) Uani 1 1 d . . . H5 H 0.7524 -0.1391 0.4807 0.138 Uiso 1 1 calc R . . C6 C 0.7659(10) -0.0773(5) 0.6748(14) 0.092(3) Uani 1 1 d . . . H6 H 0.7656 -0.1077 0.7586 0.110 Uiso 1 1 calc R . . C7 C 0.7771(11) -0.0119(5) 0.7078(15) 0.083(3) Uani 1 1 d . . . C8 C 0.8309(16) 0.1390(5) 0.9528(12) 0.090(3) Uani 1 1 d . . . C9 C 0.7152(13) 0.1496(5) 1.0606(14) 0.097(3) Uani 1 1 d . . . C10 C 0.759(2) 0.1987(7) 1.1834(13) 0.131(4) Uani 1 1 d . . . H10 H 0.6864 0.2059 1.2583 0.158 Uiso 1 1 calc R . . C11 C 0.916(3) 0.2357(6) 1.1884(19) 0.158(6) Uani 1 1 d . . . H11 H 0.9483 0.2692 1.2666 0.190 Uiso 1 1 calc R . . C12 C 1.0231(18) 0.2239(7) 1.081(2) 0.144(5) Uani 1 1 d . . . H12 H 1.1277 0.2501 1.0909 0.173 Uiso 1 1 calc R . . C13 C 0.992(2) 0.1771(5) 0.9586(16) 0.125(4) 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 Cl1 0.123(2) 0.150(3) 0.129(2) -0.0018(19) 0.0520(16) -0.001(2) F1 0.110(4) 0.097(4) 0.164(5) 0.010(3) 0.089(4) -0.010(3) O1 0.182(6) 0.087(6) 0.116(5) 0.033(4) 0.062(5) 0.041(5) O2 0.110(4) 0.082(5) 0.101(5) 0.017(4) 0.035(4) -0.012(3) N1 0.116(6) 0.073(7) 0.096(7) 0.017(6) 0.046(5) 0.021(5) N2 0.096(5) 0.070(7) 0.093(6) 0.007(6) 0.034(5) -0.001(4) C1 0.092(6) 0.057(7) 0.096(8) 0.004(7) 0.029(6) 0.001(5) C2 0.091(7) 0.059(7) 0.102(9) 0.000(7) 0.033(6) 0.016(5) C3 0.121(8) 0.102(11) 0.095(9) 0.012(7) 0.042(6) 0.035(7) C4 0.108(7) 0.114(11) 0.098(9) -0.025(8) 0.021(6) 0.021(8) C5 0.122(8) 0.098(10) 0.125(10) -0.030(9) 0.033(8) -0.001(7) C6 0.093(7) 0.068(8) 0.116(9) 0.002(7) 0.032(6) -0.017(6) C7 0.083(6) 0.067(8) 0.104(9) 0.013(8) 0.033(6) -0.005(6) C8 0.115(8) 0.068(7) 0.093(7) 0.007(6) 0.039(7) 0.010(7) C9 0.096(8) 0.082(8) 0.117(8) 0.011(6) 0.035(6) -0.016(6) C10 0.215(14) 0.092(10) 0.092(9) -0.020(8) 0.050(9) 0.028(9) C11 0.226(18) 0.063(9) 0.165(15) -0.003(9) 0.015(12) -0.020(10) C12 0.156(12) 0.097(12) 0.182(15) 0.030(10) 0.052(11) -0.024(9) C13 0.164(13) 0.047(7) 0.142(11) -0.004(8) 0.000(9) -0.026(9) _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 C9 1.658(9) . ? F1 C13 1.296(14) . ? O1 N1 1.265(8) . ? O2 N2 1.274(7) . ? N1 C1 1.380(10) . ? N1 C2 1.403(10) . ? N2 C1 1.376(9) . ? N2 C7 1.413(10) . ? C1 C8 1.474(12) . ? C2 C7 1.338(11) . ? C2 C3 1.379(11) . ? C3 C4 1.367(12) . ? C3 H3 0.9300 . ? C4 C5 1.364(12) . ? C4 H4 0.9300 . ? C5 C6 1.394(11) . ? C5 H5 0.9300 . ? C6 C7 1.377(10) . ? C6 H6 0.9300 . ? C8 C9 1.400(10) . ? C8 C13 1.415(13) . ? C9 C10 1.403(12) . ? C10 C11 1.379(14) . ? C10 H10 0.9300 . ? C11 C12 1.353(14) . ? C11 H11 0.9300 . ? C12 C13 1.367(15) . ? C12 H12 0.9300 . ? 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 N1 C1 123.4(9) . . ? O1 N1 C2 128.7(9) . . ? C1 N1 C2 107.9(8) . . ? O2 N2 C1 127.3(9) . . ? O2 N2 C7 125.3(8) . . ? C1 N2 C7 107.2(8) . . ? N2 C1 N1 107.9(9) . . ? N2 C1 C8 124.6(10) . . ? N1 C1 C8 127.4(9) . . ? C7 C2 C3 124.3(10) . . ? C7 C2 N1 108.2(10) . . ? C3 C2 N1 127.4(11) . . ? C4 C3 C2 115.0(10) . . ? C4 C3 H3 122.5 . . ? C2 C3 H3 122.5 . . ? C5 C4 C3 122.3(10) . . ? C5 C4 H4 118.9 . . ? C3 C4 H4 118.9 . . ? C4 C5 C6 121.5(10) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 116.1(9) . . ? C7 C6 H6 122.0 . . ? C5 C6 H6 122.0 . . ? C2 C7 C6 120.8(10) . . ? C2 C7 N2 108.6(10) . . ? C6 C7 N2 130.5(10) . . ? C9 C8 C13 122.7(11) . . ? C9 C8 C1 123.5(11) . . ? C13 C8 C1 113.8(10) . . ? C8 C9 C10 119.9(10) . . ? C8 C9 Cl1 118.1(11) . . ? C10 C9 Cl1 122.0(12) . . ? C11 C10 C9 117.2(11) . . ? C11 C10 H10 121.4 . . ? C9 C10 H10 121.4 . . ? C12 C11 C10 120.8(15) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 126.0(16) . . ? C11 C12 H12 117.0 . . ? C13 C12 H12 117.0 . . ? F1 C13 C12 119.6(13) . . ? F1 C13 C8 127.0(11) . . ? C12 C13 C8 113.4(14) . . ? 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 N2 C1 N1 178.5(7) . . . . ? C7 N2 C1 N1 2.9(8) . . . . ? O2 N2 C1 C8 1.4(13) . . . . ? C7 N2 C1 C8 -174.2(8) . . . . ? O1 N1 C1 N2 178.1(7) . . . . ? C2 N1 C1 N2 -1.6(8) . . . . ? O1 N1 C1 C8 -4.9(13) . . . . ? C2 N1 C1 C8 175.5(8) . . . . ? O1 N1 C2 C7 179.9(8) . . . . ? C1 N1 C2 C7 -0.5(9) . . . . ? O1 N1 C2 C3 1.9(13) . . . . ? C1 N1 C2 C3 -178.5(8) . . . . ? C7 C2 C3 C4 -0.3(13) . . . . ? N1 C2 C3 C4 177.4(8) . . . . ? C2 C3 C4 C5 1.3(14) . . . . ? C3 C4 C5 C6 0.2(15) . . . . ? C4 C5 C6 C7 -2.6(14) . . . . ? C3 C2 C7 C6 -2.1(13) . . . . ? N1 C2 C7 C6 179.7(7) . . . . ? C3 C2 C7 N2 -179.6(7) . . . . ? N1 C2 C7 N2 2.3(9) . . . . ? C5 C6 C7 C2 3.5(13) . . . . ? C5 C6 C7 N2 -179.7(8) . . . . ? O2 N2 C7 C2 -179.0(7) . . . . ? C1 N2 C7 C2 -3.3(9) . . . . ? O2 N2 C7 C6 3.9(13) . . . . ? C1 N2 C7 C6 179.6(9) . . . . ? N2 C1 C8 C9 -58.0(12) . . . . ? N1 C1 C8 C9 125.4(10) . . . . ? N2 C1 C8 C13 121.2(10) . . . . ? N1 C1 C8 C13 -55.4(12) . . . . ? C13 C8 C9 C10 -1.6(13) . . . . ? C1 C8 C9 C10 177.5(9) . . . . ? C13 C8 C9 Cl1 176.1(8) . . . . ? C1 C8 C9 Cl1 -4.9(12) . . . . ? C8 C9 C10 C11 1.7(14) . . . . ? Cl1 C9 C10 C11 -175.9(9) . . . . ? C9 C10 C11 C12 -1.3(18) . . . . ? C10 C11 C12 C13 1(2) . . . . ? C11 C12 C13 F1 -179.2(12) . . . . ? C11 C12 C13 C8 -0.5(19) . . . . ? C9 C8 C13 F1 179.5(9) . . . . ? C1 C8 C13 F1 0.3(14) . . . . ? C9 C8 C13 C12 1.0(14) . . . . ? C1 C8 C13 C12 -178.2(9) . . . . ? _diffrn_measured_fraction_theta_max 0.662 _diffrn_reflns_theta_full 24.34 _diffrn_measured_fraction_theta_full 0.662 _refine_diff_density_max 0.167 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.045 #===END data_tricl _database_code_depnum_ccdc_archive 'CCDC 228546' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2,3,6-trichlorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H6 Cl3 N2 O2' _chemical_formula_sum 'C13 H6 Cl3 N2 O2' _chemical_formula_weight 328.55 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' 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' O O 0.0106 0.0060 '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' _symmetry_space_group_name_Hall '-P 2ybc' 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 8.470(1) _cell_length_b 12.701(2) _cell_length_c 12.440(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.79(2) _cell_angle_gamma 90.00 _cell_volume 1335.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2492 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.35 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.634 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.686 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9222 _exptl_absorpt_correction_T_max 0.9600 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4437 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0942 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2433 _reflns_number_gt 1156 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0484P)^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_number_reflns 2433 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.825 _refine_ls_restrained_S_all 0.825 _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 Cl1 Cl 0.10964(12) 0.13058(7) 0.24834(7) 0.0837(3) Uani 1 1 d . . . Cl2 Cl 0.39968(13) 0.15156(8) -0.12213(7) 0.0887(4) Uani 1 1 d . . . Cl3 Cl 0.05520(13) -0.11299(8) 0.20979(9) 0.1012(4) Uani 1 1 d . . . O1 O 0.0379(3) 0.31255(19) 0.0320(2) 0.0954(8) Uani 1 1 d . . . O2 O 0.5559(3) 0.23024(18) 0.1353(2) 0.0880(8) Uani 1 1 d . . . N1 N 0.1833(4) 0.3212(2) 0.0630(2) 0.0661(7) Uani 1 1 d . . . N2 N 0.4287(3) 0.2815(2) 0.1113(2) 0.0602(7) Uani 1 1 d . . . C1 C 0.2856(4) 0.2405(2) 0.0792(2) 0.0563(8) Uani 1 1 d . . . C2 C 0.2625(4) 0.4175(2) 0.0880(2) 0.0583(8) Uani 1 1 d . . . C3 C 0.2079(5) 0.5205(3) 0.0874(3) 0.0820(11) Uani 1 1 d . . . H3 H 0.0985 0.5336 0.0665 0.098 Uiso 1 1 d R . . C4 C 0.3193(5) 0.5953(3) 0.1178(3) 0.0867(12) Uani 1 1 d . . . H4 H 0.2778 0.6656 0.1176 0.104 Uiso 1 1 d R . . C5 C 0.4751(5) 0.5697(3) 0.1463(3) 0.0800(11) Uani 1 1 d . . . H5 H 0.5499 0.6234 0.1688 0.096 Uiso 1 1 d R . . C6 C 0.5288(4) 0.4671(3) 0.1467(2) 0.0695(10) Uani 1 1 d . . . H6 H 0.6382 0.4480 0.1589 0.083 Uiso 1 1 d R . . C7 C 0.4163(4) 0.3930(2) 0.1163(2) 0.0571(8) Uani 1 1 d . . . C8 C 0.2527(4) 0.1288(2) 0.0609(2) 0.0569(8) Uani 1 1 d . . . C9 C 0.3013(4) 0.0791(3) -0.0301(3) 0.0646(9) Uani 1 1 d . . . C10 C 0.2715(4) -0.0263(3) -0.0496(3) 0.0770(11) Uani 1 1 d . . . H10 H 0.3068 -0.0571 -0.1143 0.092 Uiso 1 1 d R . . C11 C 0.1931(4) -0.0834(3) 0.0239(3) 0.0782(11) Uani 1 1 d . . . H11 H 0.1666 -0.1563 0.0133 0.094 Uiso 1 1 d R . . C12 C 0.1451(4) -0.0375(3) 0.1159(3) 0.0678(10) Uani 1 1 d . . . C13 C 0.1737(4) 0.0700(3) 0.1348(3) 0.0624(9) 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 Cl1 0.0943(8) 0.0668(6) 0.0930(6) -0.0008(5) 0.0283(5) -0.0014(5) Cl2 0.1126(9) 0.0798(7) 0.0754(6) -0.0017(5) 0.0182(6) 0.0019(6) Cl3 0.1018(9) 0.0656(7) 0.1363(9) 0.0245(6) 0.0090(6) -0.0176(6) O1 0.0644(17) 0.0575(16) 0.161(2) -0.0046(15) -0.0150(17) 0.0047(13) O2 0.0742(18) 0.0587(16) 0.128(2) 0.0032(14) -0.0193(15) 0.0086(14) N1 0.063(2) 0.0464(17) 0.089(2) -0.0014(14) 0.0031(16) 0.0067(16) N2 0.0632(19) 0.0456(16) 0.0710(17) 0.0020(13) -0.0006(14) 0.0058(15) C1 0.065(2) 0.040(2) 0.063(2) 0.0001(14) 0.0039(17) 0.0016(17) C2 0.064(2) 0.0390(19) 0.072(2) -0.0018(15) 0.0071(17) -0.0039(17) C3 0.081(3) 0.050(2) 0.115(3) -0.001(2) 0.003(2) 0.006(2) C4 0.106(4) 0.040(2) 0.115(3) -0.004(2) 0.008(3) -0.002(2) C5 0.105(3) 0.050(2) 0.085(2) -0.0028(19) 0.000(2) -0.021(2) C6 0.082(3) 0.052(2) 0.074(2) 0.0025(17) 0.0010(19) -0.013(2) C7 0.073(2) 0.042(2) 0.0569(18) 0.0017(14) 0.0064(16) -0.0001(18) C8 0.059(2) 0.0370(18) 0.074(2) -0.0011(16) -0.0012(16) 0.0049(16) C9 0.073(2) 0.048(2) 0.071(2) -0.0026(17) -0.0001(18) 0.0054(17) C10 0.089(3) 0.058(2) 0.083(2) -0.013(2) -0.004(2) 0.010(2) C11 0.083(3) 0.044(2) 0.105(3) -0.006(2) -0.014(2) 0.007(2) C12 0.062(2) 0.045(2) 0.095(3) 0.0125(18) -0.008(2) -0.0027(17) C13 0.061(2) 0.047(2) 0.078(2) -0.0019(17) -0.0005(17) 0.0012(17) _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 C13 1.727(3) . ? Cl2 C9 1.726(3) . ? Cl3 C12 1.727(3) . ? O1 N1 1.271(3) . ? O2 N2 1.277(3) . ? N1 C1 1.348(4) . ? N1 C2 1.419(4) . ? N2 C1 1.355(4) . ? N2 C7 1.422(4) . ? C1 C8 1.460(4) . ? C2 C7 1.362(4) . ? C2 C3 1.388(4) . ? C3 C4 1.374(5) . ? C3 H3 0.9599 . ? C4 C5 1.382(5) . ? C4 H4 0.9602 . ? C5 C6 1.381(5) . ? C5 H5 0.9599 . ? C6 C7 1.374(4) . ? C6 H6 0.9600 . ? C8 C9 1.383(4) . ? C8 C13 1.390(4) . ? C9 C10 1.380(5) . ? C10 C11 1.372(5) . ? C10 H10 0.9602 . ? C11 C12 1.370(5) . ? C11 H11 0.9599 . ? C12 C13 1.404(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 N1 C1 125.4(3) . . ? O1 N1 C2 125.1(3) . . ? C1 N1 C2 109.4(3) . . ? O2 N2 C1 126.7(3) . . ? O2 N2 C7 124.2(3) . . ? C1 N2 C7 109.2(3) . . ? N1 C1 N2 107.8(3) . . ? N1 C1 C8 126.9(3) . . ? N2 C1 C8 125.2(3) . . ? C7 C2 C3 121.9(3) . . ? C7 C2 N1 106.9(3) . . ? C3 C2 N1 131.2(3) . . ? C4 C3 C2 115.3(4) . . ? C4 C3 H3 126.0 . . ? C2 C3 H3 118.7 . . ? C3 C4 C5 122.3(4) . . ? C3 C4 H4 113.4 . . ? C5 C4 H4 124.2 . . ? C6 C5 C4 122.1(3) . . ? C6 C5 H5 117.3 . . ? C4 C5 H5 120.6 . . ? C7 C6 C5 115.0(3) . . ? C7 C6 H6 121.0 . . ? C5 C6 H6 123.6 . . ? C2 C7 C6 123.3(3) . . ? C2 C7 N2 106.7(3) . . ? C6 C7 N2 129.9(3) . . ? C9 C8 C13 118.6(3) . . ? C9 C8 C1 120.5(3) . . ? C13 C8 C1 120.9(3) . . ? C8 C9 C10 121.7(3) . . ? C8 C9 Cl2 118.8(3) . . ? C10 C9 Cl2 119.4(3) . . ? C11 C10 C9 119.1(3) . . ? C11 C10 H10 122.3 . . ? C9 C10 H10 118.6 . . ? C12 C11 C10 121.0(3) . . ? C12 C11 H11 116.4 . . ? C10 C11 H11 122.6 . . ? C11 C12 C13 119.8(3) . . ? C11 C12 Cl3 119.8(3) . . ? C13 C12 Cl3 120.4(3) . . ? C8 C13 C12 119.8(3) . . ? C8 C13 Cl1 119.5(2) . . ? C12 C13 Cl1 120.7(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 N1 C1 N2 179.8(3) . . . . ? C2 N1 C1 N2 -1.4(3) . . . . ? O1 N1 C1 C8 2.5(5) . . . . ? C2 N1 C1 C8 -178.7(3) . . . . ? O2 N2 C1 N1 179.4(3) . . . . ? C7 N2 C1 N1 0.3(3) . . . . ? O2 N2 C1 C8 -3.2(5) . . . . ? C7 N2 C1 C8 177.7(3) . . . . ? O1 N1 C2 C7 -179.2(3) . . . . ? C1 N1 C2 C7 1.9(3) . . . . ? O1 N1 C2 C3 1.1(6) . . . . ? C1 N1 C2 C3 -177.8(3) . . . . ? C7 C2 C3 C4 -0.3(5) . . . . ? N1 C2 C3 C4 179.3(3) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C4 C5 C6 C7 0.3(5) . . . . ? C3 C2 C7 C6 0.2(5) . . . . ? N1 C2 C7 C6 -179.5(3) . . . . ? C3 C2 C7 N2 178.1(3) . . . . ? N1 C2 C7 N2 -1.6(3) . . . . ? C5 C6 C7 C2 -0.2(5) . . . . ? C5 C6 C7 N2 -177.5(3) . . . . ? O2 N2 C7 C2 -178.3(3) . . . . ? C1 N2 C7 C2 0.8(3) . . . . ? O2 N2 C7 C6 -0.6(5) . . . . ? C1 N2 C7 C6 178.5(3) . . . . ? N1 C1 C8 C9 102.0(4) . . . . ? N2 C1 C8 C9 -74.8(4) . . . . ? N1 C1 C8 C13 -78.7(4) . . . . ? N2 C1 C8 C13 104.5(4) . . . . ? C13 C8 C9 C10 0.8(5) . . . . ? C1 C8 C9 C10 -179.8(3) . . . . ? C13 C8 C9 Cl2 -180.0(2) . . . . ? C1 C8 C9 Cl2 -0.6(4) . . . . ? C8 C9 C10 C11 -0.7(5) . . . . ? Cl2 C9 C10 C11 -179.9(3) . . . . ? C9 C10 C11 C12 -0.3(5) . . . . ? C10 C11 C12 C13 1.2(5) . . . . ? C10 C11 C12 Cl3 -176.9(3) . . . . ? C9 C8 C13 C12 0.0(5) . . . . ? C1 C8 C13 C12 -179.3(3) . . . . ? C9 C8 C13 Cl1 -179.2(2) . . . . ? C1 C8 C13 Cl1 1.4(4) . . . . ? C11 C12 C13 C8 -1.0(5) . . . . ? Cl3 C12 C13 C8 177.0(3) . . . . ? C11 C12 C13 Cl1 178.2(3) . . . . ? Cl3 C12 C13 Cl1 -3.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.161 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.039 #===END data_pentaf _database_code_depnum_ccdc_archive 'CCDC 228547' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(2,3,4,5,6-pentafluorophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H4 F5 N2 O2' _chemical_formula_sum 'C13 H4 F5 N2 O2' _chemical_formula_weight 315.18 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.536(5) _cell_length_b 7.868(2) _cell_length_c 13.760(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.69(2) _cell_angle_gamma 90.00 _cell_volume 2397.5(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3643 _cell_measurement_theta_min 1.51 _cell_measurement_theta_max 27.38 _exptl_crystal_description prism _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.746 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.171 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9747 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4241 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_sigmaI/netI 0.0940 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.38 _reflns_number_total 2373 _reflns_number_gt 1018 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 2001)' _computing_cell_refinement 'DENZO SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'DENZO SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0469P)^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_number_reflns 2373 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1275 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 0.814 _refine_ls_restrained_S_all 0.814 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 F1 F 0.11280(8) 0.5737(2) 0.77856(15) 0.0893(6) Uani 1 1 d . . . F2 F 0.16833(7) 0.3323(2) 0.49655(13) 0.0792(5) Uani 1 1 d . . . F3 F 0.26252(8) 0.5449(2) 0.51510(15) 0.0950(6) Uani 1 1 d . . . F4 F 0.28150(7) 0.7761(2) 0.66231(15) 0.1066(8) Uani 1 1 d . . . F5 F 0.20547(9) 0.7927(2) 0.79367(15) 0.1057(8) Uani 1 1 d . . . O1 O 0.00667(8) 0.5209(2) 0.61288(16) 0.0806(7) Uani 1 1 d . . . O2 O 0.14095(8) 0.0722(2) 0.64617(15) 0.0694(6) Uani 1 1 d . . . N1 N 0.02862(9) 0.3710(2) 0.62030(17) 0.0583(6) Uani 1 1 d . . . N2 N 0.09245(9) 0.1574(2) 0.63488(16) 0.0503(6) Uani 1 1 d . . . C1 C 0.08761(11) 0.3297(3) 0.6302(2) 0.0525(7) Uani 1 1 d . . . C2 C -0.00594(11) 0.2213(3) 0.6185(2) 0.0519(7) Uani 1 1 d . . . C3 C -0.06683(11) 0.1967(3) 0.6071(2) 0.0658(8) Uani 1 1 d . . . H3 H -0.0937 0.2925 0.6006 0.079 Uiso 1 1 d R . . C4 C -0.08636(9) 0.0307(3) 0.60674(15) 0.0680(8) Uani 1 1 d . . . H4 H -0.1291 0.0107 0.5948 0.082 Uiso 1 1 d R . . C5 C -0.04569(9) -0.1042(3) 0.61609(15) 0.0612(8) Uani 1 1 d R . . H5 H -0.0622 -0.2163 0.6186 0.073 Uiso 1 1 d R . . C6 C 0.01574(12) -0.0797(3) 0.62662(19) 0.0551(8) Uani 1 1 d . . . H6 H 0.0488 -0.1843 0.6374 0.066 Uiso 1 1 d R . . C7 C 0.03392(10) 0.0875(3) 0.62721(19) 0.0482(7) Uani 1 1 d . . . C8 C 0.13716(12) 0.4488(3) 0.6367(2) 0.0535(7) Uani 1 1 d . . . C9 C 0.17650(12) 0.4453(3) 0.5713(2) 0.0586(8) Uani 1 1 d . . . C10 C 0.22414(13) 0.5543(4) 0.5798(3) 0.0646(8) Uani 1 1 d . . . C11 C 0.23401(14) 0.6723(4) 0.6534(3) 0.0736(10) Uani 1 1 d . . . C12 C 0.19586(15) 0.6798(3) 0.7200(3) 0.0727(10) Uani 1 1 d . . . C13 C 0.14834(13) 0.5697(3) 0.7102(3) 0.0617(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.1090(15) 0.0740(11) 0.0890(16) -0.0241(10) 0.0288(12) -0.0130(9) F2 0.0795(11) 0.0852(11) 0.0746(13) -0.0127(10) 0.0186(9) -0.0092(9) F3 0.0715(12) 0.1155(14) 0.0988(17) 0.0258(12) 0.0180(11) -0.0098(10) F4 0.0897(12) 0.0922(12) 0.1227(18) 0.0271(12) -0.0196(12) -0.0450(10) F5 0.1292(16) 0.0700(10) 0.1041(16) -0.0248(10) -0.0139(13) -0.0254(10) O1 0.0822(13) 0.0447(10) 0.1133(19) -0.0049(11) 0.0134(12) 0.0119(10) O2 0.0563(11) 0.0560(10) 0.0925(16) 0.0001(10) 0.0054(10) 0.0089(9) N1 0.0658(15) 0.0418(11) 0.0664(18) -0.0036(11) 0.0098(13) 0.0035(11) N2 0.0535(13) 0.0422(12) 0.0550(16) -0.0013(10) 0.0095(11) 0.0058(10) C1 0.0548(16) 0.0433(15) 0.060(2) -0.0038(13) 0.0114(14) -0.0019(12) C2 0.0550(15) 0.0477(14) 0.0540(19) -0.0025(13) 0.0123(13) -0.0027(12) C3 0.0565(17) 0.0671(17) 0.073(2) -0.0025(16) 0.0094(15) 0.0059(13) C4 0.0537(16) 0.083(2) 0.067(2) -0.0073(17) 0.0105(15) -0.0131(15) C5 0.0682(18) 0.0550(16) 0.060(2) -0.0032(14) 0.0111(16) -0.0166(14) C6 0.0651(17) 0.0484(14) 0.049(2) -0.0004(13) 0.0039(15) -0.0049(12) C7 0.0511(15) 0.0457(14) 0.0466(18) -0.0026(12) 0.0055(13) -0.0058(12) C8 0.0573(17) 0.0441(14) 0.058(2) -0.0018(14) 0.0084(15) -0.0042(12) C9 0.0605(18) 0.0485(15) 0.062(2) -0.0017(15) -0.0015(16) -0.0048(14) C10 0.0575(18) 0.0711(19) 0.066(2) 0.0198(18) 0.0136(18) -0.0028(17) C11 0.071(2) 0.0568(18) 0.082(3) 0.0160(19) -0.013(2) -0.0193(16) C12 0.087(2) 0.0466(16) 0.073(3) -0.0043(17) -0.016(2) -0.0130(16) C13 0.0704(19) 0.0540(16) 0.060(2) 0.0008(16) 0.0093(17) -0.0022(15) _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 F1 C13 1.344(3) . ? F2 C9 1.346(3) . ? F3 C10 1.353(3) . ? F4 C11 1.334(3) . ? F5 C12 1.335(3) . ? O1 N1 1.276(2) . ? O2 N2 1.267(2) . ? N1 C1 1.351(3) . ? N1 C2 1.409(3) . ? N2 C1 1.361(3) . ? N2 C7 1.415(3) . ? C1 C8 1.447(3) . ? C2 C3 1.366(3) . ? C2 C7 1.375(3) . ? C3 C4 1.378(3) . ? C3 H3 0.9600 . ? C4 C5 1.3923 . ? C4 H4 0.9598 . ? C5 C6 1.379(3) . ? C5 H5 0.9600 . ? C6 C7 1.378(3) . ? C6 H6 1.1020 . ? C8 C9 1.375(4) . ? C8 C13 1.378(4) . ? C9 C10 1.362(4) . ? C10 C11 1.362(4) . ? C11 C12 1.369(4) . ? C12 C13 1.365(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 N1 C1 126.1(2) . . ? O1 N1 C2 124.5(2) . . ? C1 N1 C2 109.35(19) . . ? O2 N2 C1 126.4(2) . . ? O2 N2 C7 125.09(18) . . ? C1 N2 C7 108.5(2) . . ? N1 C1 N2 108.2(2) . . ? N1 C1 C8 125.8(2) . . ? N2 C1 C8 126.0(2) . . ? C3 C2 C7 121.9(2) . . ? C3 C2 N1 131.3(2) . . ? C7 C2 N1 106.8(2) . . ? C2 C3 C4 116.6(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 123.3 . . ? C3 C4 C5 121.18(14) . . ? C3 C4 H4 117.8 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 122.29(13) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 116.8 . . ? C5 C6 C7 115.2(2) . . ? C5 C6 H6 123.4 . . ? C7 C6 H6 121.3 . . ? C2 C7 C6 122.8(2) . . ? C2 C7 N2 107.11(19) . . ? C6 C7 N2 130.1(2) . . ? C9 C8 C13 116.2(3) . . ? C9 C8 C1 122.0(2) . . ? C13 C8 C1 121.7(3) . . ? F2 C9 C10 118.4(3) . . ? F2 C9 C8 120.0(2) . . ? C10 C9 C8 121.7(3) . . ? F3 C10 C9 120.0(3) . . ? F3 C10 C11 119.4(3) . . ? C9 C10 C11 120.7(3) . . ? F4 C11 C10 120.2(4) . . ? F4 C11 C12 120.3(3) . . ? C10 C11 C12 119.4(3) . . ? F5 C12 C13 120.7(4) . . ? F5 C12 C11 120.2(3) . . ? C13 C12 C11 119.1(3) . . ? F1 C13 C12 118.4(3) . . ? F1 C13 C8 118.6(3) . . ? C12 C13 C8 122.9(3) . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.870 _refine_diff_density_max 0.140 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.038 #===END data_metacn _database_code_depnum_ccdc_archive 'CCDC 228548' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-(3-cyanophenyl)benzimidazolyl-N,N'-dioxide' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 N3 O2' _chemical_formula_sum 'C14 H8 N3 O2' _chemical_formula_weight 250.23 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.722(1) _cell_length_b 7.138(2) _cell_length_c 13.316(1) _cell_angle_alpha 90.00 _cell_angle_beta 118.23(2) _cell_angle_gamma 90.00 _cell_volume 1149.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1811 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.82 _exptl_crystal_description prism _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9420 _exptl_absorpt_correction_T_max 0.9608 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 KappaCCD' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3277 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0893 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.82 _reflns_number_total 1994 _reflns_number_gt 1019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius 2001)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material ? _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^)+(0.0758P)^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_number_reflns 1994 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _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 O1 O -0.07749(15) 0.4921(3) 0.29051(17) 0.0689(7) Uani 1 1 d . . . O2 O 0.02499(15) -0.1212(3) 0.41338(17) 0.0670(6) Uani 1 1 d . . . N1 N -0.07917(17) 0.3147(3) 0.30554(18) 0.0525(6) Uani 1 1 d . . . N2 N -0.03047(18) 0.0253(3) 0.36198(19) 0.0522(6) Uani 1 1 d . . . N3 N 0.4703(3) -0.0483(6) 0.6217(3) 0.1117(13) Uani 1 1 d . . . C1 C 0.0086(2) 0.2050(4) 0.3738(2) 0.0499(7) Uani 1 1 d . . . C2 C -0.1760(2) 0.2044(4) 0.2514(2) 0.0503(7) Uani 1 1 d . . . C3 C -0.2828(2) 0.2555(5) 0.1776(2) 0.0642(9) Uani 1 1 d . . . H3 H -0.3081 0.4041 0.1517 0.077 Uiso 1 1 d R . . C4 C -0.3584(2) 0.1100(5) 0.1394(3) 0.0708(9) Uani 1 1 d . . . H4 H -0.4342 0.1335 0.0848 0.085 Uiso 1 1 d R . . C5 C -0.3287(2) -0.0743(5) 0.1739(2) 0.0686(9) Uani 1 1 d . . . H5 H -0.3861 -0.1673 0.1474 0.082 Uiso 1 1 d R . . C6 C -0.2195(2) -0.1229(4) 0.2483(2) 0.0611(8) Uani 1 1 d . . . H6 H -0.1956 -0.2538 0.2803 0.073 Uiso 1 1 d R . . C7 C -0.1449(2) 0.0228(4) 0.2857(2) 0.0505(7) Uani 1 1 d . . . C8 C 0.1209(2) 0.2661(4) 0.4472(2) 0.0517(7) Uani 1 1 d . . . C9 C 0.2074(2) 0.1365(4) 0.4844(2) 0.0568(8) Uani 1 1 d . . . H9 H 0.1892 -0.0078 0.4602 0.068 Uiso 1 1 d R . . C10 C 0.3145(2) 0.1971(5) 0.5579(2) 0.0630(8) Uani 1 1 d . . . C11 C 0.3361(3) 0.3807(5) 0.5945(3) 0.0717(9) Uani 1 1 d . . . H11 H 0.4112 0.4155 0.6449 0.086 Uiso 1 1 d R . . C12 C 0.2510(3) 0.5074(5) 0.5564(3) 0.0700(9) Uani 1 1 d . . . H12 H 0.2681 0.6342 0.5830 0.084 Uiso 1 1 d R . . C13 C 0.1433(2) 0.4533(4) 0.4829(2) 0.0608(8) Uani 1 1 d . . . H13 H 0.0826 0.5400 0.4548 0.073 Uiso 1 1 d R . . C14 C 0.4028(3) 0.0605(6) 0.5951(3) 0.0772(10) 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 O1 0.0793(14) 0.0430(14) 0.0796(15) 0.0080(10) 0.0337(12) 0.0083(11) O2 0.0676(12) 0.0432(13) 0.0829(14) 0.0118(11) 0.0296(11) 0.0096(10) N1 0.0620(15) 0.0397(15) 0.0575(15) 0.0045(12) 0.0296(12) 0.0072(12) N2 0.0564(15) 0.0422(15) 0.0593(15) 0.0031(12) 0.0284(12) 0.0069(12) N3 0.069(2) 0.138(3) 0.103(3) 0.005(2) 0.0194(18) 0.028(2) C1 0.0586(17) 0.0381(17) 0.0543(17) 0.0007(14) 0.0277(14) 0.0049(15) C2 0.0502(17) 0.0493(19) 0.0521(17) -0.0036(14) 0.0247(14) 0.0010(14) C3 0.0589(19) 0.067(2) 0.0638(19) 0.0050(16) 0.0270(16) 0.0104(17) C4 0.0523(18) 0.087(3) 0.068(2) -0.001(2) 0.0242(15) 0.0053(19) C5 0.0574(19) 0.081(3) 0.068(2) -0.0124(18) 0.0306(16) -0.0119(18) C6 0.067(2) 0.0547(19) 0.0648(19) -0.0022(16) 0.0334(16) -0.0044(16) C7 0.0510(17) 0.0489(19) 0.0524(17) -0.0023(14) 0.0252(14) 0.0028(14) C8 0.0546(17) 0.0505(19) 0.0517(17) 0.0006(14) 0.0265(14) -0.0022(15) C9 0.0530(17) 0.059(2) 0.0543(17) 0.0018(15) 0.0218(14) -0.0008(15) C10 0.0553(19) 0.073(2) 0.0589(19) 0.0022(18) 0.0258(15) -0.0007(17) C11 0.0624(19) 0.090(3) 0.059(2) -0.007(2) 0.0259(16) -0.017(2) C12 0.079(2) 0.063(2) 0.072(2) -0.0141(17) 0.0384(19) -0.018(2) C13 0.068(2) 0.055(2) 0.0636(19) -0.0048(16) 0.0349(16) -0.0055(15) C14 0.058(2) 0.096(3) 0.065(2) 0.001(2) 0.0189(17) 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 O1 N1 1.284(3) . ? O2 N2 1.284(3) . ? N1 C1 1.362(3) . ? N1 C2 1.414(3) . ? N2 C1 1.370(3) . ? N2 C7 1.411(3) . ? N3 C14 1.129(4) . ? C1 C8 1.447(4) . ? C2 C3 1.372(4) . ? C2 C7 1.373(4) . ? C3 C4 1.384(4) . ? C3 H3 1.1186 . ? C4 C5 1.389(4) . ? C4 H4 0.9601 . ? C5 C6 1.394(4) . ? C5 H5 0.9600 . ? C6 C7 1.376(4) . ? C6 H6 1.0154 . ? C8 C9 1.398(4) . ? C8 C13 1.403(4) . ? C9 C10 1.395(4) . ? C9 H9 1.0732 . ? C10 C11 1.380(4) . ? C10 C14 1.448(5) . ? C11 C12 1.371(4) . ? C11 H11 0.9601 . ? C12 C13 1.387(4) . ? C12 H12 0.9600 . ? C13 H13 0.9601 . ? 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 N1 C1 126.6(2) . . ? O1 N1 C2 123.5(2) . . ? C1 N1 C2 109.9(2) . . ? O2 N2 C1 126.9(2) . . ? O2 N2 C7 123.4(2) . . ? C1 N2 C7 109.7(2) . . ? N1 C1 N2 106.7(2) . . ? N1 C1 C8 126.9(3) . . ? N2 C1 C8 126.4(2) . . ? C3 C2 C7 123.2(3) . . ? C3 C2 N1 130.1(3) . . ? C7 C2 N1 106.7(2) . . ? C2 C3 C4 115.2(3) . . ? C2 C3 H3 122.9 . . ? C4 C3 H3 121.9 . . ? C3 C4 C5 122.5(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 117.4 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 118.2 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 115.8(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 123.6 . . ? C2 C7 C6 122.2(3) . . ? C2 C7 N2 107.0(2) . . ? C6 C7 N2 130.9(3) . . ? C9 C8 C13 119.8(2) . . ? C9 C8 C1 119.6(3) . . ? C13 C8 C1 120.5(3) . . ? C10 C9 C8 118.7(3) . . ? C10 C9 H9 121.8 . . ? C8 C9 H9 119.4 . . ? C11 C10 C9 121.4(3) . . ? C11 C10 C14 120.9(3) . . ? C9 C10 C14 117.7(3) . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 122.2 . . ? C10 C11 H11 118.2 . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 118.0 . . ? C13 C12 H12 121.0 . . ? C12 C13 C8 119.6(3) . . ? C12 C13 H13 122.3 . . ? C8 C13 H13 118.1 . . ? N3 C14 C10 178.3(4) . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 25.0 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.247 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.120