# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'C Aakeroy' _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; Cyanoximes as effective and selective co-crystallizing agents ; loop_ _publ_author_name 'C Aakeroy' 'John Desper' 'Debra J Salmon' 'Michelle M Smith' # Attachment 'xray.cif.cif' data_A1 _database_code_depnum_ccdc_archive 'CCDC 694148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-bromo-PhC(CN)(=NOH)), 3-bromo-5-methoxypyridine ; _chemical_name_common '(4-bromo-PhC(CN)(=NOH)), 3-bromo-5-methoxypyridine' _chemical_melting_point ? _chemical_formula_moiety ; (C8 H5 Br N2 O) (C6 H6 Br N O) ; _chemical_formula_sum 'C14 H11 Br2 N3 O2' _chemical_formula_weight 413.08 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' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9907(6) _cell_length_b 8.0552(7) _cell_length_c 15.3027(13) _cell_angle_alpha 79.305(5) _cell_angle_beta 89.038(5) _cell_angle_gamma 64.660(5) _cell_volume 763.37(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2866 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.85 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 5.316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.225 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5513 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3350 _reflns_number_gt 2663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 3350 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1704 _refine_ls_wR_factor_gt 0.1633 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.05763(9) 0.83758(7) -0.12842(4) 0.0358(2) Uani 1 1 d . . . Br2 Br 0.97220(8) 0.16580(7) 0.65616(4) 0.0388(2) Uani 1 1 d . . . C11 C 0.3337(8) 0.3529(7) 0.1193(3) 0.0268(10) Uani 1 1 d . . . C12 C 0.2131(9) 0.5349(7) 0.1292(4) 0.0344(11) Uani 1 1 d . . . H12 H 0.1874 0.5611 0.1874 0.041 Uiso 1 1 calc R . . C13 C 0.1297(9) 0.6787(7) 0.0567(4) 0.0375(12) Uani 1 1 d . . . H13 H 0.0478 0.8035 0.0647 0.045 Uiso 1 1 calc R . . C14 C 0.1656(8) 0.6407(7) -0.0272(3) 0.0302(10) Uani 1 1 d . . . C15 C 0.2846(8) 0.4590(7) -0.0405(4) 0.0331(11) Uani 1 1 d . . . H15 H 0.3081 0.4340 -0.0990 0.040 Uiso 1 1 calc R . . C16 C 0.3683(8) 0.3150(7) 0.0339(3) 0.0292(10) Uani 1 1 d . . . H16 H 0.4497 0.1900 0.0263 0.035 Uiso 1 1 calc R . . N17 N 0.4219(7) 0.2355(6) 0.2753(3) 0.0299(9) Uani 1 1 d . . . O17 O 0.5096(6) 0.0768(5) 0.3392(3) 0.0323(8) Uani 1 1 d . . . H17 H 0.468(8) 0.150(7) 0.391(4) 0.039 Uiso 1 1 d . . . C17 C 0.4264(7) 0.1979(6) 0.1965(3) 0.0265(10) Uani 1 1 d . . . N18 N 0.5938(10) -0.1440(7) 0.1746(4) 0.0529(14) Uani 1 1 d . . . C18 C 0.5165(9) 0.0079(7) 0.1850(4) 0.0350(12) Uani 1 1 d . . . N21 N 0.5011(7) 0.2106(6) 0.4868(3) 0.0301(9) Uani 1 1 d . . . C22 C 0.6884(8) 0.1593(7) 0.5295(3) 0.0302(10) Uani 1 1 d . . . H22 H 0.8130 0.0680 0.5109 0.036 Uiso 1 1 calc R . . C23 C 0.7028(8) 0.2371(7) 0.6000(3) 0.0273(10) Uani 1 1 d . . . C24 C 0.5236(7) 0.3694(6) 0.6302(3) 0.0254(9) Uani 1 1 d . . . H24 H 0.5331 0.4229 0.6793 0.030 Uiso 1 1 calc R . . O25 O 0.1405(5) 0.5481(5) 0.6032(3) 0.0352(8) Uani 1 1 d . . . C25 C 0.3314(8) 0.4190(7) 0.5852(3) 0.0284(10) Uani 1 1 d . . . C26 C 0.3280(8) 0.3364(7) 0.5137(3) 0.0294(10) Uani 1 1 d . . . H26 H 0.1956 0.3718 0.4827 0.035 Uiso 1 1 calc R . . C27 C 0.1339(8) 0.6196(8) 0.6787(4) 0.0382(12) Uani 1 1 d . . . H27A H -0.0116 0.7102 0.6844 0.057 Uiso 1 1 calc R . . H27B H 0.2280 0.6822 0.6743 0.057 Uiso 1 1 calc R . . H27C H 0.1807 0.5175 0.7311 0.057 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0433(3) 0.0295(3) 0.0325(3) 0.0000(2) -0.0036(2) -0.0160(2) Br2 0.0273(3) 0.0384(3) 0.0448(4) -0.0031(3) -0.0054(2) -0.0103(2) C11 0.030(2) 0.029(2) 0.023(2) -0.006(2) 0.002(2) -0.014(2) C12 0.041(3) 0.034(3) 0.029(3) -0.014(2) 0.006(2) -0.013(2) C13 0.041(3) 0.028(3) 0.043(3) -0.018(2) 0.006(3) -0.009(2) C14 0.038(3) 0.026(2) 0.028(3) 0.000(2) 0.000(2) -0.017(2) C15 0.044(3) 0.034(3) 0.027(3) -0.010(2) 0.004(2) -0.021(2) C16 0.032(3) 0.026(2) 0.029(3) -0.007(2) 0.005(2) -0.011(2) N17 0.032(2) 0.033(2) 0.026(2) -0.0029(18) -0.0005(18) -0.0167(19) O17 0.039(2) 0.0268(18) 0.029(2) -0.0053(15) -0.0018(16) -0.0121(16) C17 0.026(2) 0.025(2) 0.026(3) -0.0031(19) -0.0015(19) -0.0103(19) N18 0.078(4) 0.028(3) 0.042(3) -0.011(2) 0.009(3) -0.011(3) C18 0.046(3) 0.031(3) 0.026(3) -0.006(2) 0.001(2) -0.014(2) N21 0.038(2) 0.027(2) 0.024(2) -0.0022(17) 0.0000(18) -0.0132(18) C22 0.033(3) 0.024(2) 0.028(3) -0.004(2) 0.004(2) -0.007(2) C23 0.027(2) 0.026(2) 0.025(3) 0.0014(19) -0.002(2) -0.010(2) C24 0.028(2) 0.025(2) 0.023(2) -0.0031(19) 0.0013(19) -0.0124(19) O25 0.0245(17) 0.038(2) 0.038(2) -0.0058(17) 0.0005(16) -0.0092(15) C25 0.030(2) 0.030(2) 0.026(3) -0.003(2) 0.004(2) -0.015(2) C26 0.029(2) 0.036(3) 0.026(3) -0.004(2) 0.001(2) -0.017(2) C27 0.028(3) 0.034(3) 0.046(3) -0.007(2) 0.010(2) -0.007(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 C14 1.894(5) . ? Br2 C23 1.887(5) . ? C11 C12 1.380(7) . ? C11 C16 1.391(7) . ? C11 C17 1.470(7) . ? C12 C13 1.370(8) . ? C12 H12 0.9500 . ? C13 C14 1.370(8) . ? C13 H13 0.9500 . ? C14 C15 1.392(7) . ? C15 C16 1.391(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N17 C17 1.293(6) . ? N17 O17 1.361(5) . ? O17 H17 1.03(5) . ? C17 C18 1.429(6) . ? N18 C18 1.148(7) . ? N21 C26 1.322(7) . ? N21 C22 1.333(6) . ? C22 C23 1.368(7) . ? C22 H22 0.9500 . ? C23 C24 1.392(7) . ? C24 C25 1.381(7) . ? C24 H24 0.9500 . ? O25 C25 1.358(6) . ? O25 C27 1.375(7) . ? C25 C26 1.388(7) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? 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 C12 C11 C16 119.0(5) . . ? C12 C11 C17 121.8(5) . . ? C16 C11 C17 119.1(4) . . ? C13 C12 C11 121.4(5) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 119.3(5) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 121.4(5) . . ? C13 C14 Br1 120.2(4) . . ? C15 C14 Br1 118.4(4) . . ? C16 C15 C14 118.4(5) . . ? C16 C15 H15 120.8 . . ? C14 C15 H15 120.8 . . ? C11 C16 C15 120.5(5) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C17 N17 O17 111.7(4) . . ? N17 O17 H17 93(3) . . ? N17 C17 C18 120.3(5) . . ? N17 C17 C11 119.2(4) . . ? C18 C17 C11 120.5(4) . . ? N18 C18 C17 178.0(6) . . ? C26 N21 C22 119.4(4) . . ? N21 C22 C23 120.6(5) . . ? N21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C22 C23 C24 121.5(4) . . ? C22 C23 Br2 119.1(4) . . ? C24 C23 Br2 119.4(4) . . ? C25 C24 C23 116.8(5) . . ? C25 C24 H24 121.6 . . ? C23 C24 H24 121.6 . . ? C25 O25 C27 117.3(4) . . ? O25 C25 C24 125.6(5) . . ? O25 C25 C26 115.6(5) . . ? C24 C25 C26 118.9(5) . . ? N21 C26 C25 122.9(5) . . ? N21 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? O25 C27 H27A 109.5 . . ? O25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? 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 C16 C11 C12 C13 -0.9(7) . . . . ? C17 C11 C12 C13 179.1(4) . . . . ? C11 C12 C13 C14 0.4(8) . . . . ? C12 C13 C14 C15 0.2(7) . . . . ? C12 C13 C14 Br1 -178.6(4) . . . . ? C13 C14 C15 C16 -0.3(7) . . . . ? Br1 C14 C15 C16 178.5(3) . . . . ? C12 C11 C16 C15 0.7(7) . . . . ? C17 C11 C16 C15 -179.3(4) . . . . ? C14 C15 C16 C11 -0.2(7) . . . . ? O17 N17 C17 C18 -0.1(6) . . . . ? O17 N17 C17 C11 178.6(4) . . . . ? C12 C11 C17 N17 -10.3(7) . . . . ? C16 C11 C17 N17 169.7(4) . . . . ? C12 C11 C17 C18 168.4(5) . . . . ? C16 C11 C17 C18 -11.6(7) . . . . ? C26 N21 C22 C23 -0.7(7) . . . . ? N21 C22 C23 C24 0.9(7) . . . . ? N21 C22 C23 Br2 -178.1(3) . . . . ? C22 C23 C24 C25 -0.4(7) . . . . ? Br2 C23 C24 C25 178.6(3) . . . . ? C27 O25 C25 C24 -8.0(7) . . . . ? C27 O25 C25 C26 173.8(4) . . . . ? C23 C24 C25 O25 -178.4(4) . . . . ? C23 C24 C25 C26 -0.3(7) . . . . ? C22 N21 C26 C25 -0.1(7) . . . . ? O25 C25 C26 N21 178.8(4) . . . . ? C24 C25 C26 N21 0.5(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O17 H17 N21 1.03(5) 1.69(5) 2.667(6) 157(5) . _diffrn_measured_fraction_theta_max 0.917 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.735 _refine_diff_density_min -1.056 _refine_diff_density_rms 0.201 #END data_A2 _database_code_depnum_ccdc_archive 'CCDC 694149' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)-2-methylbenzimidazole ; _chemical_name_common ;(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)-2- methylbenzimidazole ; _chemical_melting_point ? _chemical_formula_moiety ; (C8 H5 Br N2 O) (C15 H13 Br N2) ; _chemical_formula_sum 'C23 H18 Br2 N4 O' _chemical_formula_weight 526.23 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 4.9374(6) _cell_length_b 22.597(3) _cell_length_c 19.233(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.869(2) _cell_angle_gamma 90.00 _cell_volume 2130.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6131 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 29.25 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 3.828 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.656 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24200 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 30.02 _reflns_number_total 6170 _reflns_number_gt 4792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^2^+0.2000P] 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 6170 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.79725(4) 0.584899(9) 0.108998(11) 0.02328(7) Uani 1 1 d . . . Br2 Br 0.98977(5) 0.082854(10) 0.607905(12) 0.03154(7) Uani 1 1 d . . . N11 N 1.0656(3) 0.33215(7) 0.40216(8) 0.0177(3) Uani 1 1 d . . . C12 C 0.9769(4) 0.38499(8) 0.42489(10) 0.0183(4) Uani 1 1 d . . . N13 N 0.7625(3) 0.40511(7) 0.38408(9) 0.0199(3) Uani 1 1 d . . . C14 C 0.7083(4) 0.36362(9) 0.33081(10) 0.0191(4) Uani 1 1 d . . . C15 C 0.5066(4) 0.36263(9) 0.27378(11) 0.0239(4) Uani 1 1 d . . . H15 H 0.3788 0.3940 0.2656 0.029 Uiso 1 1 calc R . . C16 C 0.4987(4) 0.31447(10) 0.22953(11) 0.0266(5) Uani 1 1 d . . . H16 H 0.3628 0.3128 0.1902 0.032 Uiso 1 1 calc R . . C17 C 0.6869(5) 0.26781(10) 0.24132(11) 0.0259(4) Uani 1 1 d . . . H17 H 0.6761 0.2354 0.2096 0.031 Uiso 1 1 calc R . . C18 C 0.8886(4) 0.26806(9) 0.29829(10) 0.0220(4) Uani 1 1 d . . . H18 H 1.0149 0.2364 0.3069 0.026 Uiso 1 1 calc R . . C19 C 0.8952(4) 0.31692(8) 0.34186(10) 0.0179(4) Uani 1 1 d . . . C20 C 1.1097(4) 0.41633(9) 0.48765(11) 0.0229(4) Uani 1 1 d . . . H20A H 0.9870 0.4471 0.5015 0.034 Uiso 1 1 calc R . . H20B H 1.2797 0.4346 0.4767 0.034 Uiso 1 1 calc R . . H20C H 1.1501 0.3880 0.5261 0.034 Uiso 1 1 calc R . . C21 C 1.0839(4) 0.14893(9) 0.55455(10) 0.0216(4) Uani 1 1 d . . . C22 C 1.2784(4) 0.14221(9) 0.50941(11) 0.0220(4) Uani 1 1 d . . . H22 H 1.3683 0.1054 0.5057 0.026 Uiso 1 1 calc R . . C23 C 1.3403(4) 0.19036(9) 0.46940(10) 0.0200(4) Uani 1 1 d . . . H23 H 1.4719 0.1862 0.4375 0.024 Uiso 1 1 calc R . . C24 C 1.2130(4) 0.24451(8) 0.47521(10) 0.0166(4) Uani 1 1 d . . . C25 C 1.0188(4) 0.25003(9) 0.52163(10) 0.0205(4) Uani 1 1 d . . . H25 H 0.9306 0.2870 0.5260 0.025 Uiso 1 1 calc R . . C26 C 0.9526(4) 0.20231(9) 0.56154(10) 0.0216(4) Uani 1 1 d . . . H26 H 0.8197 0.2062 0.5931 0.026 Uiso 1 1 calc R . . C27 C 1.2963(4) 0.29677(8) 0.43392(10) 0.0184(4) Uani 1 1 d . . . H27A H 1.4190 0.3224 0.4653 0.022 Uiso 1 1 calc R . . H27B H 1.4006 0.2823 0.3965 0.022 Uiso 1 1 calc R . . C31 C -0.0566(4) 0.56230(9) 0.28222(10) 0.0173(4) Uani 1 1 d . . . C32 C -0.1707(4) 0.51289(9) 0.24598(10) 0.0188(4) Uani 1 1 d . . . H32 H -0.0957 0.4747 0.2564 0.023 Uiso 1 1 calc R . . C33 C -0.3923(4) 0.51911(9) 0.19497(10) 0.0200(4) Uani 1 1 d . . . H33 H -0.4700 0.4855 0.1706 0.024 Uiso 1 1 calc R . . C34 C -0.4988(4) 0.57502(9) 0.18006(10) 0.0201(4) Uani 1 1 d . . . C35 C -0.3942(4) 0.62431(9) 0.21586(11) 0.0217(4) Uani 1 1 d . . . H35 H -0.4722 0.6622 0.2056 0.026 Uiso 1 1 calc R . . C36 C -0.1725(4) 0.61785(9) 0.26735(10) 0.0204(4) Uani 1 1 d . . . H36 H -0.0996 0.6516 0.2925 0.025 Uiso 1 1 calc R . . C37 C 0.1841(4) 0.55582(8) 0.33487(10) 0.0171(4) Uani 1 1 d . . . N37 N 0.3056(3) 0.50563(7) 0.34499(9) 0.0200(3) Uani 1 1 d . . . O37 O 0.5254(3) 0.50814(6) 0.39558(7) 0.0222(3) Uani 1 1 d . . . H37 H 0.605(5) 0.4708(11) 0.3903(12) 0.027 Uiso 1 1 d . . . C38 C 0.2888(4) 0.60833(9) 0.37292(10) 0.0202(4) Uani 1 1 d . . . N38 N 0.3689(4) 0.65001(8) 0.40247(10) 0.0276(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 Br1 0.01765(11) 0.02759(12) 0.02355(11) 0.00635(8) -0.00185(7) -0.00213(8) Br2 0.03395(14) 0.02558(13) 0.03329(13) 0.01385(9) -0.00345(10) -0.00552(9) N11 0.0182(8) 0.0145(8) 0.0196(8) 0.0031(6) -0.0010(6) 0.0018(6) C12 0.0207(10) 0.0139(9) 0.0202(9) 0.0020(7) 0.0014(7) -0.0017(7) N13 0.0211(8) 0.0136(8) 0.0240(8) 0.0032(6) -0.0014(7) 0.0003(6) C14 0.0191(9) 0.0168(9) 0.0209(9) 0.0061(7) 0.0002(7) -0.0005(7) C15 0.0224(10) 0.0234(11) 0.0242(10) 0.0078(8) -0.0037(8) -0.0009(8) C16 0.0268(11) 0.0313(12) 0.0197(10) 0.0059(9) -0.0056(8) -0.0080(9) C17 0.0327(12) 0.0228(11) 0.0220(10) -0.0024(8) 0.0022(8) -0.0090(9) C18 0.0252(10) 0.0177(10) 0.0230(10) 0.0014(8) 0.0023(8) -0.0010(8) C19 0.0183(9) 0.0173(9) 0.0178(9) 0.0050(7) 0.0009(7) -0.0009(7) C20 0.0263(11) 0.0182(10) 0.0228(10) 0.0003(8) -0.0028(8) -0.0009(8) C21 0.0234(10) 0.0173(10) 0.0216(10) 0.0049(8) -0.0071(8) -0.0044(8) C22 0.0239(10) 0.0138(9) 0.0265(10) 0.0016(8) -0.0045(8) 0.0031(8) C23 0.0177(9) 0.0196(10) 0.0220(9) -0.0014(8) -0.0008(7) 0.0025(8) C24 0.0151(8) 0.0150(9) 0.0183(9) 0.0010(7) -0.0033(7) 0.0004(7) C25 0.0215(9) 0.0178(10) 0.0222(9) 0.0001(8) 0.0023(8) 0.0031(8) C26 0.0214(10) 0.0228(10) 0.0203(9) 0.0017(8) 0.0013(8) -0.0004(8) C27 0.0149(9) 0.0158(9) 0.0239(9) 0.0042(7) -0.0004(7) 0.0017(7) C31 0.0171(9) 0.0187(9) 0.0164(9) 0.0013(7) 0.0028(7) 0.0021(7) C32 0.0200(9) 0.0153(9) 0.0209(9) 0.0021(7) 0.0020(7) 0.0019(7) C33 0.0207(10) 0.0174(10) 0.0220(10) -0.0001(8) 0.0029(8) -0.0021(7) C34 0.0163(9) 0.0255(11) 0.0184(9) 0.0029(8) 0.0023(7) 0.0002(8) C35 0.0215(10) 0.0203(10) 0.0229(10) 0.0031(8) 0.0014(8) 0.0058(8) C36 0.0240(10) 0.0163(10) 0.0209(9) -0.0005(7) 0.0018(8) 0.0030(8) C37 0.0198(9) 0.0160(9) 0.0157(8) 0.0006(7) 0.0033(7) 0.0016(7) N37 0.0192(8) 0.0211(9) 0.0189(8) 0.0041(6) -0.0003(6) 0.0025(7) O37 0.0249(8) 0.0186(8) 0.0214(7) 0.0005(6) -0.0044(6) 0.0047(6) C38 0.0205(10) 0.0210(10) 0.0186(9) 0.0021(8) 0.0004(7) 0.0058(8) N38 0.0300(10) 0.0229(10) 0.0282(9) -0.0022(8) -0.0034(8) 0.0070(8) _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 C34 1.899(2) . ? Br2 C21 1.901(2) . ? N11 C12 1.362(2) . ? N11 C19 1.392(2) . ? N11 C27 1.464(2) . ? C12 N13 1.321(2) . ? C12 C20 1.483(3) . ? N13 C14 1.391(3) . ? C14 C15 1.391(3) . ? C14 C19 1.401(3) . ? C15 C16 1.379(3) . ? C15 H15 0.9500 . ? C16 C17 1.406(3) . ? C16 H16 0.9500 . ? C17 C18 1.389(3) . ? C17 H17 0.9500 . ? C18 C19 1.384(3) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.378(3) . ? C21 C26 1.384(3) . ? C22 C23 1.388(3) . ? C22 H22 0.9500 . ? C23 C24 1.386(3) . ? C23 H23 0.9500 . ? C24 C25 1.391(3) . ? C24 C27 1.508(3) . ? C25 C26 1.385(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C36 1.395(3) . ? C31 C32 1.399(3) . ? C31 C37 1.474(3) . ? C32 C33 1.387(3) . ? C32 H32 0.9500 . ? C33 C34 1.385(3) . ? C33 H33 0.9500 . ? C34 C35 1.377(3) . ? C35 C36 1.393(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N37 1.287(2) . ? C37 C38 1.456(3) . ? N37 O37 1.369(2) . ? O37 H37 0.94(2) . ? C38 N38 1.146(3) . ? 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 C12 N11 C19 107.37(16) . . ? C12 N11 C27 127.52(17) . . ? C19 N11 C27 125.10(16) . . ? N13 C12 N11 112.14(17) . . ? N13 C12 C20 124.35(18) . . ? N11 C12 C20 123.51(18) . . ? C12 N13 C14 106.01(16) . . ? C15 C14 N13 130.43(19) . . ? C15 C14 C19 120.25(19) . . ? N13 C14 C19 109.31(17) . . ? C16 C15 C14 117.7(2) . . ? C16 C15 H15 121.2 . . ? C14 C15 H15 121.2 . . ? C15 C16 C17 121.52(19) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 121.44(19) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C19 C18 C17 116.33(19) . . ? C19 C18 H18 121.8 . . ? C17 C18 H18 121.8 . . ? C18 C19 N11 132.05(18) . . ? C18 C19 C14 122.79(18) . . ? N11 C19 C14 105.16(17) . . ? C12 C20 H20A 109.5 . . ? C12 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C12 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 121.81(18) . . ? C22 C21 Br2 119.19(15) . . ? C26 C21 Br2 119.00(15) . . ? C21 C22 C23 118.65(18) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C24 C23 C22 121.02(18) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C25 119.00(17) . . ? C23 C24 C27 119.60(17) . . ? C25 C24 C27 121.34(17) . . ? C26 C25 C24 120.79(18) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C21 C26 C25 118.72(18) . . ? C21 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? N11 C27 C24 113.56(15) . . ? N11 C27 H27A 108.9 . . ? C24 C27 H27A 108.9 . . ? N11 C27 H27B 108.9 . . ? C24 C27 H27B 108.9 . . ? H27A C27 H27B 107.7 . . ? C36 C31 C32 119.03(18) . . ? C36 C31 C37 120.51(18) . . ? C32 C31 C37 120.45(17) . . ? C33 C32 C31 120.56(18) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 119.14(19) . . ? C34 C33 H33 120.4 . . ? C32 C33 H33 120.4 . . ? C35 C34 C33 121.58(19) . . ? C35 C34 Br1 118.48(15) . . ? C33 C34 Br1 119.93(15) . . ? C34 C35 C36 119.10(18) . . ? C34 C35 H35 120.5 . . ? C36 C35 H35 120.5 . . ? C35 C36 C31 120.55(19) . . ? C35 C36 H36 119.7 . . ? C31 C36 H36 119.7 . . ? N37 C37 C38 120.75(18) . . ? N37 C37 C31 120.96(17) . . ? C38 C37 C31 118.22(17) . . ? C37 N37 O37 112.73(16) . . ? N37 O37 H37 101.1(14) . . ? N38 C38 C37 179.2(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N11 C12 N13 0.0(2) . . . . ? C27 N11 C12 N13 -179.97(17) . . . . ? C19 N11 C12 C20 -179.11(18) . . . . ? C27 N11 C12 C20 0.9(3) . . . . ? N11 C12 N13 C14 -0.8(2) . . . . ? C20 C12 N13 C14 178.36(18) . . . . ? C12 N13 C14 C15 -179.8(2) . . . . ? C12 N13 C14 C19 1.2(2) . . . . ? N13 C14 C15 C16 -178.7(2) . . . . ? C19 C14 C15 C16 0.2(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C17 C18 C19 N11 -179.54(19) . . . . ? C17 C18 C19 C14 1.0(3) . . . . ? C12 N11 C19 C18 -178.8(2) . . . . ? C27 N11 C19 C18 1.2(3) . . . . ? C12 N11 C19 C14 0.7(2) . . . . ? C27 N11 C19 C14 -179.29(16) . . . . ? C15 C14 C19 C18 -0.7(3) . . . . ? N13 C14 C19 C18 178.38(18) . . . . ? C15 C14 C19 N11 179.72(17) . . . . ? N13 C14 C19 N11 -1.2(2) . . . . ? C26 C21 C22 C23 -0.9(3) . . . . ? Br2 C21 C22 C23 178.35(15) . . . . ? C21 C22 C23 C24 1.0(3) . . . . ? C22 C23 C24 C25 -0.5(3) . . . . ? C22 C23 C24 C27 176.61(18) . . . . ? C23 C24 C25 C26 -0.1(3) . . . . ? C27 C24 C25 C26 -177.14(18) . . . . ? C22 C21 C26 C25 0.3(3) . . . . ? Br2 C21 C26 C25 -178.91(15) . . . . ? C24 C25 C26 C21 0.2(3) . . . . ? C12 N11 C27 C24 102.4(2) . . . . ? C19 N11 C27 C24 -77.6(2) . . . . ? C23 C24 C27 N11 137.61(18) . . . . ? C25 C24 C27 N11 -45.3(3) . . . . ? C36 C31 C32 C33 1.3(3) . . . . ? C37 C31 C32 C33 -178.12(17) . . . . ? C31 C32 C33 C34 0.3(3) . . . . ? C32 C33 C34 C35 -1.6(3) . . . . ? C32 C33 C34 Br1 178.63(14) . . . . ? C33 C34 C35 C36 1.3(3) . . . . ? Br1 C34 C35 C36 -178.97(15) . . . . ? C34 C35 C36 C31 0.4(3) . . . . ? C32 C31 C36 C35 -1.7(3) . . . . ? C37 C31 C36 C35 177.77(18) . . . . ? C36 C31 C37 N37 -174.42(18) . . . . ? C32 C31 C37 N37 5.0(3) . . . . ? C36 C31 C37 C38 2.8(3) . . . . ? C32 C31 C37 C38 -177.78(17) . . . . ? C38 C37 N37 O37 2.6(2) . . . . ? C31 C37 N37 O37 179.70(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O37 H37 N13 0.94(2) 1.69(3) 2.627(2) 177(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.678 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.092 #END data_A3 _database_code_depnum_ccdc_archive 'CCDC 694150' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)benzimidazole ; _chemical_name_common '(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)benzimidazole' _chemical_melting_point ? _chemical_formula_moiety ; (C8 H5 Br N2 O) (C14 H11 Br N2) ; _chemical_formula_sum 'C22 H16 Br2 N4 O' _chemical_formula_weight 512.21 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' 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' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.3033(6) _cell_length_b 13.2294(15) _cell_length_c 15.0601(17) _cell_angle_alpha 102.536(2) _cell_angle_beta 99.505(2) _cell_angle_gamma 94.752(2) _cell_volume 1009.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6500 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.685 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 4.036 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.519 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11582 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 30.05 _reflns_number_total 5763 _reflns_number_gt 4972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0450P)^2^+0.0800P] 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 5763 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0736 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.23446(3) 0.130843(14) -0.100585(11) 0.02864(6) Uani 1 1 d . . . Br2 Br -0.26182(3) 0.594556(12) 0.943098(11) 0.02674(6) Uani 1 1 d . . . N11 N 0.7222(2) 0.20505(10) 0.36245(9) 0.0205(2) Uani 1 1 d . . . C12 C 0.6814(3) 0.15263(13) 0.42790(10) 0.0227(3) Uani 1 1 d . . . H12 H 0.7577 0.0916 0.4349 0.027 Uiso 1 1 calc R . . N13 N 0.5251(3) 0.19506(11) 0.48079(9) 0.0231(3) Uani 1 1 d . . . C14 C 0.4559(3) 0.28111(12) 0.44730(10) 0.0200(3) Uani 1 1 d . . . C15 C 0.2866(3) 0.35243(13) 0.47458(11) 0.0229(3) Uani 1 1 d . . . H15 H 0.1998 0.3481 0.5242 0.028 Uiso 1 1 calc R . . C16 C 0.2509(3) 0.42954(13) 0.42628(11) 0.0247(3) Uani 1 1 d . . . H16 H 0.1358 0.4786 0.4429 0.030 Uiso 1 1 calc R . . C17 C 0.3800(3) 0.43723(13) 0.35342(11) 0.0240(3) Uani 1 1 d . . . H17 H 0.3528 0.4921 0.3228 0.029 Uiso 1 1 calc R . . C18 C 0.5459(3) 0.36667(13) 0.32523(11) 0.0224(3) Uani 1 1 d . . . H18 H 0.6328 0.3714 0.2756 0.027 Uiso 1 1 calc R . . C19 C 0.5790(3) 0.28848(12) 0.37322(10) 0.0193(3) Uani 1 1 d . . . C21 C 0.4374(3) 0.14174(12) 0.01856(10) 0.0212(3) Uani 1 1 d . . . C22 C 0.6791(3) 0.19932(12) 0.04224(11) 0.0224(3) Uani 1 1 d . . . H22 H 0.7472 0.2308 -0.0012 0.027 Uiso 1 1 calc R . . C23 C 0.8194(3) 0.20998(12) 0.13078(11) 0.0210(3) Uani 1 1 d . . . H23 H 0.9853 0.2494 0.1481 0.025 Uiso 1 1 calc R . . C24 C 0.7209(3) 0.16379(12) 0.19472(10) 0.0193(3) Uani 1 1 d . . . C25 C 0.4796(3) 0.10480(12) 0.16856(11) 0.0218(3) Uani 1 1 d . . . H25 H 0.4125 0.0719 0.2113 0.026 Uiso 1 1 calc R . . C26 C 0.3359(3) 0.09369(12) 0.08019(11) 0.0222(3) Uani 1 1 d . . . H26 H 0.1707 0.0538 0.0624 0.027 Uiso 1 1 calc R . . C27 C 0.8775(3) 0.17743(13) 0.29080(11) 0.0230(3) Uani 1 1 d . . . H27A H 0.9492 0.1117 0.2959 0.028 Uiso 1 1 calc R . . H27B H 1.0235 0.2329 0.3010 0.028 Uiso 1 1 calc R . . C31 C -0.0552(3) 0.30103(12) 0.74697(10) 0.0204(3) Uani 1 1 d . . . C32 C 0.0847(3) 0.39889(13) 0.75905(11) 0.0229(3) Uani 1 1 d . . . H32 H 0.2204 0.4060 0.7260 0.027 Uiso 1 1 calc R . . C33 C 0.0273(3) 0.48555(13) 0.81884(11) 0.0232(3) Uani 1 1 d . . . H33 H 0.1239 0.5519 0.8275 0.028 Uiso 1 1 calc R . . C34 C -0.1741(3) 0.47412(12) 0.86604(10) 0.0214(3) Uani 1 1 d . . . C35 C -0.3143(3) 0.37825(13) 0.85578(11) 0.0230(3) Uani 1 1 d . . . H35 H -0.4499 0.3715 0.8890 0.028 Uiso 1 1 calc R . . C36 C -0.2540(3) 0.29203(13) 0.79621(11) 0.0226(3) Uani 1 1 d . . . H36 H -0.3493 0.2257 0.7887 0.027 Uiso 1 1 calc R . . C37 C 0.0083(3) 0.20877(12) 0.68401(10) 0.0209(3) Uani 1 1 d . . . N37 N 0.1827(3) 0.21829(11) 0.63470(9) 0.0234(3) Uani 1 1 d . . . O37 O 0.2217(2) 0.12539(9) 0.58132(8) 0.0265(2) Uani 1 1 d . . . H37 H 0.343(4) 0.1444(17) 0.5500(15) 0.032 Uiso 1 1 d . . . C38 C -0.1244(3) 0.10712(13) 0.67962(11) 0.0244(3) Uani 1 1 d . . . N38 N -0.2271(3) 0.02743(12) 0.67896(11) 0.0321(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03113(9) 0.03444(10) 0.01932(8) 0.00539(7) 0.00148(6) 0.00714(7) Br2 0.03070(9) 0.02431(9) 0.02757(9) 0.00635(7) 0.01164(7) 0.00380(6) N11 0.0184(5) 0.0253(6) 0.0180(6) 0.0057(5) 0.0035(5) 0.0023(5) C12 0.0227(7) 0.0254(8) 0.0192(7) 0.0067(6) 0.0012(5) 0.0007(6) N13 0.0260(6) 0.0247(7) 0.0185(6) 0.0053(5) 0.0043(5) 0.0012(5) C14 0.0192(6) 0.0237(7) 0.0148(6) 0.0028(5) 0.0011(5) -0.0012(5) C15 0.0227(7) 0.0258(8) 0.0190(7) 0.0020(6) 0.0060(6) 0.0001(6) C16 0.0239(7) 0.0265(8) 0.0224(7) 0.0022(6) 0.0041(6) 0.0049(6) C17 0.0248(7) 0.0249(8) 0.0220(7) 0.0069(6) 0.0017(6) 0.0030(6) C18 0.0219(7) 0.0274(8) 0.0184(7) 0.0071(6) 0.0040(6) 0.0014(6) C19 0.0157(6) 0.0233(7) 0.0167(6) 0.0027(5) 0.0010(5) -0.0003(5) C21 0.0244(7) 0.0208(7) 0.0180(7) 0.0024(5) 0.0038(5) 0.0066(6) C22 0.0253(7) 0.0221(7) 0.0220(7) 0.0063(6) 0.0090(6) 0.0038(6) C23 0.0198(6) 0.0198(7) 0.0237(7) 0.0047(6) 0.0065(6) 0.0014(5) C24 0.0198(6) 0.0185(7) 0.0197(7) 0.0026(5) 0.0059(5) 0.0040(5) C25 0.0233(7) 0.0215(7) 0.0219(7) 0.0063(6) 0.0072(6) 0.0008(6) C26 0.0217(7) 0.0201(7) 0.0227(7) 0.0016(6) 0.0038(6) 0.0001(5) C27 0.0189(6) 0.0308(8) 0.0213(7) 0.0074(6) 0.0069(6) 0.0056(6) C31 0.0201(6) 0.0254(7) 0.0180(6) 0.0103(6) 0.0027(5) 0.0039(5) C32 0.0215(7) 0.0267(8) 0.0238(7) 0.0109(6) 0.0069(6) 0.0035(6) C33 0.0216(7) 0.0237(8) 0.0266(8) 0.0106(6) 0.0054(6) 0.0015(6) C34 0.0234(7) 0.0246(7) 0.0186(7) 0.0087(6) 0.0047(5) 0.0054(6) C35 0.0217(7) 0.0275(8) 0.0230(7) 0.0104(6) 0.0074(6) 0.0028(6) C36 0.0209(7) 0.0249(8) 0.0220(7) 0.0077(6) 0.0038(6) -0.0018(6) C37 0.0225(7) 0.0233(7) 0.0187(7) 0.0095(6) 0.0024(5) 0.0034(6) N37 0.0260(6) 0.0257(7) 0.0200(6) 0.0079(5) 0.0050(5) 0.0041(5) O37 0.0314(6) 0.0248(6) 0.0260(6) 0.0066(5) 0.0112(5) 0.0048(5) C38 0.0264(7) 0.0273(8) 0.0213(7) 0.0081(6) 0.0062(6) 0.0040(6) N38 0.0358(8) 0.0286(8) 0.0347(8) 0.0104(6) 0.0115(6) 0.0017(6) _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 C21 1.9035(15) . ? Br2 C34 1.8973(15) . ? N11 C12 1.357(2) . ? N11 C19 1.3867(19) . ? N11 C27 1.4656(18) . ? C12 N13 1.318(2) . ? C12 H12 0.9500 . ? N13 C14 1.394(2) . ? C14 C19 1.399(2) . ? C14 C15 1.400(2) . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 C17 1.403(2) . ? C16 H16 0.9500 . ? C17 C18 1.383(2) . ? C17 H17 0.9500 . ? C18 C19 1.391(2) . ? C18 H18 0.9500 . ? C21 C22 1.386(2) . ? C21 C26 1.386(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.394(2) . ? C23 H23 0.9500 . ? C24 C25 1.392(2) . ? C24 C27 1.510(2) . ? C25 C26 1.391(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C36 1.397(2) . ? C31 C32 1.398(2) . ? C31 C37 1.474(2) . ? C32 C33 1.385(2) . ? C32 H32 0.9500 . ? C33 C34 1.393(2) . ? C33 H33 0.9500 . ? C34 C35 1.381(2) . ? C35 C36 1.385(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N37 1.2923(19) . ? C37 C38 1.448(2) . ? N37 O37 1.3666(18) . ? O37 H37 0.91(2) . ? C38 N38 1.143(2) . ? 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 C12 N11 C19 106.91(12) . . ? C12 N11 C27 127.27(13) . . ? C19 N11 C27 125.76(13) . . ? N13 C12 N11 113.06(14) . . ? N13 C12 H12 123.5 . . ? N11 C12 H12 123.5 . . ? C12 N13 C14 105.17(13) . . ? N13 C14 C19 109.42(13) . . ? N13 C14 C15 130.30(14) . . ? C19 C14 C15 120.25(14) . . ? C16 C15 C14 117.28(14) . . ? C16 C15 H15 121.4 . . ? C14 C15 H15 121.4 . . ? C15 C16 C17 121.80(14) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 121.49(15) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 116.56(14) . . ? C17 C18 H18 121.7 . . ? C19 C18 H18 121.7 . . ? N11 C19 C18 131.95(14) . . ? N11 C19 C14 105.44(13) . . ? C18 C19 C14 122.61(14) . . ? C22 C21 C26 121.78(14) . . ? C22 C21 Br1 119.42(12) . . ? C26 C21 Br1 118.79(12) . . ? C21 C22 C23 118.50(14) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C22 C23 C24 121.04(14) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 119.26(14) . . ? C25 C24 C27 120.93(14) . . ? C23 C24 C27 119.81(14) . . ? C26 C25 C24 120.43(14) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C21 C26 C25 118.97(14) . . ? C21 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? N11 C27 C24 111.82(12) . . ? N11 C27 H27A 109.3 . . ? C24 C27 H27A 109.3 . . ? N11 C27 H27B 109.3 . . ? C24 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C36 C31 C32 118.92(14) . . ? C36 C31 C37 120.68(14) . . ? C32 C31 C37 120.39(13) . . ? C33 C32 C31 120.56(14) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 119.06(15) . . ? C32 C33 H33 120.5 . . ? C34 C33 H33 120.5 . . ? C35 C34 C33 121.53(14) . . ? C35 C34 Br2 119.78(11) . . ? C33 C34 Br2 118.66(12) . . ? C34 C35 C36 118.86(14) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? C35 C36 C31 121.06(15) . . ? C35 C36 H36 119.5 . . ? C31 C36 H36 119.5 . . ? N37 C37 C38 120.57(14) . . ? N37 C37 C31 120.51(14) . . ? C38 C37 C31 118.91(13) . . ? C37 N37 O37 113.26(13) . . ? N37 O37 H37 103.2(14) . . ? N38 C38 C37 177.96(18) . . ? 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 C19 N11 C12 N13 -0.37(18) . . . . ? C27 N11 C12 N13 -177.81(14) . . . . ? N11 C12 N13 C14 0.57(18) . . . . ? C12 N13 C14 C19 -0.55(16) . . . . ? C12 N13 C14 C15 177.26(16) . . . . ? N13 C14 C15 C16 -178.37(15) . . . . ? C19 C14 C15 C16 -0.8(2) . . . . ? C14 C15 C16 C17 -0.6(2) . . . . ? C15 C16 C17 C18 1.2(2) . . . . ? C16 C17 C18 C19 -0.4(2) . . . . ? C12 N11 C19 C18 -179.23(16) . . . . ? C27 N11 C19 C18 -1.7(3) . . . . ? C12 N11 C19 C14 0.00(16) . . . . ? C27 N11 C19 C14 177.49(14) . . . . ? C17 C18 C19 N11 178.16(15) . . . . ? C17 C18 C19 C14 -1.0(2) . . . . ? N13 C14 C19 N11 0.34(16) . . . . ? C15 C14 C19 N11 -177.73(13) . . . . ? N13 C14 C19 C18 179.66(14) . . . . ? C15 C14 C19 C18 1.6(2) . . . . ? C26 C21 C22 C23 -1.1(2) . . . . ? Br1 C21 C22 C23 177.29(11) . . . . ? C21 C22 C23 C24 0.2(2) . . . . ? C22 C23 C24 C25 1.0(2) . . . . ? C22 C23 C24 C27 -179.57(14) . . . . ? C23 C24 C25 C26 -1.3(2) . . . . ? C27 C24 C25 C26 179.31(14) . . . . ? C22 C21 C26 C25 0.8(2) . . . . ? Br1 C21 C26 C25 -177.56(11) . . . . ? C24 C25 C26 C21 0.4(2) . . . . ? C12 N11 C27 C24 122.20(16) . . . . ? C19 N11 C27 C24 -54.8(2) . . . . ? C25 C24 C27 N11 -47.02(19) . . . . ? C23 C24 C27 N11 133.55(14) . . . . ? C36 C31 C32 C33 0.0(2) . . . . ? C37 C31 C32 C33 -179.35(14) . . . . ? C31 C32 C33 C34 -0.7(2) . . . . ? C32 C33 C34 C35 1.2(2) . . . . ? C32 C33 C34 Br2 -176.98(12) . . . . ? C33 C34 C35 C36 -0.8(2) . . . . ? Br2 C34 C35 C36 177.35(12) . . . . ? C34 C35 C36 C31 0.0(2) . . . . ? C32 C31 C36 C35 0.4(2) . . . . ? C37 C31 C36 C35 179.75(14) . . . . ? C36 C31 C37 N37 176.15(14) . . . . ? C32 C31 C37 N37 -4.5(2) . . . . ? C36 C31 C37 C38 -5.0(2) . . . . ? C32 C31 C37 C38 174.35(14) . . . . ? C38 C37 N37 O37 0.1(2) . . . . ? C31 C37 N37 O37 178.92(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O37 H37 N13 0.91(2) 1.73(2) 2.6260(18) 168(2) . _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.776 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.080 #END data_A4 _database_code_depnum_ccdc_archive 'CCDC 694151' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-bromo-PhC(CN)(N=OH), (3-[(5,6-dimethylbenzimidazol-1-yl)methyl]PhCN ; _chemical_name_common ;4-bromo-PhC(CN)(N=OH), (3-((5,6-dimethylbenzimidazol-1- yl)methyl)PhCN ; _chemical_melting_point ? _chemical_formula_moiety ; (C8 H5 N2 O Br) (C17 H15 N3) ; _chemical_formula_sum 'C25 H20 Br N5 O' _chemical_formula_weight 486.37 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' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.039(3) _cell_length_b 13.982(6) _cell_length_c 14.166(6) _cell_angle_alpha 70.067(19) _cell_angle_beta 83.78(3) _cell_angle_gamma 82.22(3) _cell_volume 1111.6(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1383 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 18.50 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.877 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16974 _diffrn_reflns_av_R_equivalents 0.2759 _diffrn_reflns_av_sigmaI/netI 0.3704 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.39 _reflns_number_total 4980 _reflns_number_gt 1475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0700P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.059(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4980 _refine_ls_number_parameters 292 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2524 _refine_ls_R_factor_gt 0.0716 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 0.795 _refine_ls_restrained_S_all 0.795 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.87028(15) -0.02316(7) 0.27426(7) 0.0698(5) Uani 1 1 d . . . N11 N 0.2436(9) 0.5147(4) 0.3121(4) 0.0393(15) Uani 1 1 d . . . C12 C 0.3975(11) 0.4939(6) 0.3819(6) 0.046(2) Uani 1 1 d . . . H12 H 0.3778 0.5204 0.4361 0.055 Uiso 1 1 calc R . . N13 N 0.5742(9) 0.4345(4) 0.3675(4) 0.0394(15) Uani 1 1 d . . . C14 C 0.5398(10) 0.4154(5) 0.2800(5) 0.0313(17) Uani 1 1 d . . . C15 C 0.6713(11) 0.3583(5) 0.2282(5) 0.0367(18) Uani 1 1 d . . . H15 H 0.8156 0.3274 0.2494 0.044 Uiso 1 1 calc R . . C16 C 0.5925(11) 0.3467(5) 0.1464(5) 0.0374(18) Uani 1 1 d . . . C17 C 0.3817(11) 0.3987(5) 0.1116(5) 0.0364(18) Uani 1 1 d . . . C18 C 0.2526(11) 0.4570(5) 0.1621(5) 0.0386(18) Uani 1 1 d . . . H18 H 0.1108 0.4908 0.1399 0.046 Uiso 1 1 calc R . . C19 C 0.3351(10) 0.4651(5) 0.2459(5) 0.0322(17) Uani 1 1 d . . . C20 C 0.7284(12) 0.2818(6) 0.0915(5) 0.049(2) Uani 1 1 d . . . H20A H 0.8762 0.2596 0.1188 0.074 Uiso 1 1 calc R . . H20B H 0.7462 0.3217 0.0197 0.074 Uiso 1 1 calc R . . H20C H 0.6517 0.2217 0.0999 0.074 Uiso 1 1 calc R . . C21 C 0.3023(12) 0.3865(6) 0.0206(5) 0.049(2) Uani 1 1 d . . . H21A H 0.1495 0.4203 0.0098 0.074 Uiso 1 1 calc R . . H21B H 0.3035 0.3136 0.0304 0.074 Uiso 1 1 calc R . . H21C H 0.4016 0.4178 -0.0383 0.074 Uiso 1 1 calc R . . C31 C -0.0516(11) 0.8194(6) 0.0754(6) 0.0377(18) Uani 1 1 d . . . C32 C -0.0838(10) 0.7282(6) 0.1497(5) 0.0344(17) Uani 1 1 d . . . H32 H -0.2107 0.6945 0.1506 0.041 Uiso 1 1 calc R . . C33 C 0.0669(10) 0.6850(5) 0.2236(5) 0.0337(17) Uani 1 1 d . . . C34 C 0.2479(11) 0.7397(6) 0.2223(6) 0.046(2) Uani 1 1 d . . . H34 H 0.3500 0.7130 0.2739 0.055 Uiso 1 1 calc R . . C35 C 0.2785(12) 0.8302(6) 0.1482(6) 0.046(2) Uani 1 1 d . . . H35 H 0.4026 0.8654 0.1480 0.056 Uiso 1 1 calc R . . C36 C 0.1295(12) 0.8713(6) 0.0730(6) 0.046(2) Uani 1 1 d . . . H36 H 0.1514 0.9341 0.0208 0.055 Uiso 1 1 calc R . . C37 C -0.2049(14) 0.8626(6) -0.0011(7) 0.048(2) Uani 1 1 d . . . N37 N -0.3323(12) 0.9012(5) -0.0629(5) 0.059(2) Uani 1 1 d . . . C38 C 0.0379(10) 0.5844(5) 0.3056(5) 0.0370(18) Uani 1 1 d . . . H38A H -0.0006 0.5960 0.3708 0.044 Uiso 1 1 calc R . . H38B H -0.0868 0.5531 0.2914 0.044 Uiso 1 1 calc R . . C41 C 1.3779(11) 0.1796(5) 0.4220(5) 0.0339(17) Uani 1 1 d . . . C42 C 1.3148(12) 0.1538(5) 0.3447(5) 0.0419(19) Uani 1 1 d . . . H42 H 1.1682 0.1769 0.3222 0.050 Uiso 1 1 calc R . . C43 C 1.4590(12) 0.0949(6) 0.2981(5) 0.047(2) Uani 1 1 d . . . H43 H 1.4161 0.0806 0.2421 0.056 Uiso 1 1 calc R . . C44 C 1.6683(12) 0.0572(5) 0.3359(6) 0.0422(19) Uani 1 1 d . . . C45 C 1.7330(12) 0.0804(6) 0.4144(6) 0.048(2) Uani 1 1 d . . . H45 H 1.8766 0.0543 0.4393 0.058 Uiso 1 1 calc R . . C46 C 1.5890(11) 0.1418(6) 0.4576(6) 0.047(2) Uani 1 1 d . . . H46 H 1.6344 0.1583 0.5119 0.056 Uiso 1 1 calc R . . C47 C 1.2305(11) 0.2470(5) 0.4664(5) 0.0347(18) Uani 1 1 d . . . N47 N 1.0380(9) 0.2893(5) 0.4295(4) 0.0423(15) Uani 1 1 d . . . O47 O 0.9228(7) 0.3514(4) 0.4782(3) 0.0457(13) Uani 1 1 d . . . H47 H 0.8012 0.3766 0.4515 0.069 Uiso 1 1 calc R . . C48 C 1.3040(11) 0.2691(6) 0.5517(6) 0.043(2) Uani 1 1 d . . . N48 N 1.3630(9) 0.2891(5) 0.6150(5) 0.059(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 Br1 0.0678(7) 0.0662(8) 0.0744(8) -0.0319(5) 0.0147(5) 0.0039(5) N11 0.035(3) 0.048(4) 0.029(3) -0.008(3) 0.001(3) -0.002(3) C12 0.038(4) 0.060(6) 0.039(5) -0.021(4) -0.003(4) 0.008(4) N13 0.034(3) 0.042(4) 0.040(4) -0.012(3) -0.002(3) 0.000(3) C14 0.021(4) 0.040(5) 0.035(4) -0.017(4) -0.001(3) -0.002(3) C15 0.028(4) 0.041(5) 0.039(5) -0.009(4) -0.002(3) -0.008(3) C16 0.042(4) 0.041(5) 0.031(4) -0.014(4) 0.011(4) -0.011(4) C17 0.041(4) 0.035(5) 0.034(4) -0.010(4) 0.000(4) -0.010(4) C18 0.044(4) 0.040(5) 0.033(5) -0.015(4) 0.005(4) -0.006(4) C19 0.033(4) 0.034(4) 0.035(4) -0.020(4) 0.001(3) -0.003(3) C20 0.049(5) 0.053(5) 0.044(5) -0.018(4) 0.006(4) -0.001(4) C21 0.054(5) 0.057(6) 0.042(5) -0.023(4) -0.003(4) -0.009(4) C31 0.035(4) 0.045(5) 0.041(5) -0.024(4) -0.003(4) -0.005(4) C32 0.028(4) 0.050(5) 0.027(4) -0.016(4) 0.006(3) -0.008(4) C33 0.023(4) 0.043(5) 0.038(5) -0.019(4) 0.000(3) -0.001(4) C34 0.036(4) 0.057(6) 0.050(5) -0.025(5) -0.009(4) 0.003(4) C35 0.037(4) 0.035(5) 0.062(6) -0.010(4) -0.008(4) -0.002(4) C36 0.047(5) 0.042(5) 0.049(5) -0.018(4) 0.004(4) -0.004(4) C37 0.060(6) 0.027(5) 0.055(6) -0.013(4) 0.003(5) -0.010(4) N37 0.068(5) 0.060(5) 0.049(5) -0.015(4) -0.004(4) -0.015(4) C38 0.020(3) 0.056(5) 0.032(4) -0.015(4) -0.001(3) 0.007(4) C41 0.038(4) 0.032(4) 0.029(4) -0.007(4) 0.005(3) -0.006(3) C42 0.040(4) 0.049(5) 0.038(5) -0.018(4) 0.004(4) -0.007(4) C43 0.049(5) 0.055(5) 0.031(5) -0.009(4) 0.005(4) -0.009(4) C44 0.051(5) 0.031(5) 0.040(5) -0.009(4) 0.005(4) -0.004(4) C45 0.039(4) 0.051(5) 0.056(6) -0.021(5) -0.002(4) -0.001(4) C46 0.036(4) 0.056(6) 0.046(5) -0.012(4) -0.001(4) -0.007(4) C47 0.027(4) 0.039(5) 0.039(5) -0.014(4) 0.004(3) -0.007(3) N47 0.036(3) 0.048(4) 0.044(4) -0.018(3) 0.005(3) -0.005(3) O47 0.034(3) 0.062(4) 0.044(3) -0.024(3) -0.007(2) 0.009(3) C48 0.031(4) 0.059(6) 0.042(5) -0.022(4) 0.001(4) -0.003(4) N48 0.038(4) 0.094(6) 0.054(5) -0.038(4) -0.006(3) 0.002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C44 1.892(7) . ? N11 C12 1.362(8) . ? N11 C19 1.376(8) . ? N11 C38 1.462(8) . ? C12 N13 1.303(8) . ? C12 H12 0.9500 . ? N13 C14 1.396(8) . ? C14 C15 1.381(9) . ? C14 C19 1.383(8) . ? C15 C16 1.365(9) . ? C15 H15 0.9500 . ? C16 C17 1.426(9) . ? C16 C20 1.498(9) . ? C17 C18 1.375(9) . ? C17 C21 1.492(9) . ? C18 C19 1.381(9) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C31 C32 1.370(9) . ? C31 C36 1.384(9) . ? C31 C37 1.420(11) . ? C32 C33 1.384(9) . ? C32 H32 0.9500 . ? C33 C34 1.412(9) . ? C33 C38 1.507(9) . ? C34 C35 1.361(10) . ? C34 H34 0.9500 . ? C35 C36 1.387(10) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N37 1.166(9) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C41 C42 1.369(9) . ? C41 C46 1.391(9) . ? C41 C47 1.459(9) . ? C42 C43 1.387(9) . ? C42 H42 0.9500 . ? C43 C44 1.391(9) . ? C43 H43 0.9500 . ? C44 C45 1.368(10) . ? C45 C46 1.381(10) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 N47 1.307(8) . ? C47 C48 1.470(10) . ? N47 O47 1.362(7) . ? O47 H47 0.8400 . ? C48 N48 1.130(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 C12 N11 C19 105.4(6) . . ? C12 N11 C38 125.7(6) . . ? C19 N11 C38 128.6(6) . . ? N13 C12 N11 113.9(6) . . ? N13 C12 H12 123.0 . . ? N11 C12 H12 123.0 . . ? C12 N13 C14 104.9(6) . . ? C15 C14 C19 120.2(6) . . ? C15 C14 N13 131.0(6) . . ? C19 C14 N13 108.8(6) . . ? C16 C15 C14 119.5(6) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 119.8(6) . . ? C15 C16 C20 120.5(7) . . ? C17 C16 C20 119.7(7) . . ? C18 C17 C16 120.6(7) . . ? C18 C17 C21 120.8(7) . . ? C16 C17 C21 118.6(6) . . ? C17 C18 C19 118.1(7) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? N11 C19 C18 131.2(6) . . ? N11 C19 C14 107.0(6) . . ? C18 C19 C14 121.7(6) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C32 C31 C36 121.1(7) . . ? C32 C31 C37 120.3(7) . . ? C36 C31 C37 118.6(7) . . ? C31 C32 C33 120.5(6) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C32 C33 C34 118.0(7) . . ? C32 C33 C38 121.9(6) . . ? C34 C33 C38 120.1(6) . . ? C35 C34 C33 120.9(7) . . ? C35 C34 H34 119.5 . . ? C33 C34 H34 119.5 . . ? C34 C35 C36 120.4(7) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 118.9(7) . . ? C31 C36 H36 120.6 . . ? C35 C36 H36 120.6 . . ? N37 C37 C31 177.5(8) . . ? N11 C38 C33 110.5(5) . . ? N11 C38 H38A 109.5 . . ? C33 C38 H38A 109.5 . . ? N11 C38 H38B 109.5 . . ? C33 C38 H38B 109.5 . . ? H38A C38 H38B 108.1 . . ? C42 C41 C46 118.9(7) . . ? C42 C41 C47 121.5(6) . . ? C46 C41 C47 119.6(7) . . ? C41 C42 C43 121.8(7) . . ? C41 C42 H42 119.1 . . ? C43 C42 H42 119.1 . . ? C42 C43 C44 118.0(7) . . ? C42 C43 H43 121.0 . . ? C44 C43 H43 121.0 . . ? C45 C44 C43 121.0(7) . . ? C45 C44 Br1 119.6(6) . . ? C43 C44 Br1 119.4(6) . . ? C44 C45 C46 119.9(7) . . ? C44 C45 H45 120.1 . . ? C46 C45 H45 120.1 . . ? C45 C46 C41 120.3(7) . . ? C45 C46 H46 119.9 . . ? C41 C46 H46 119.9 . . ? N47 C47 C41 120.7(6) . . ? N47 C47 C48 120.1(6) . . ? C41 C47 C48 119.1(6) . . ? C47 N47 O47 113.4(6) . . ? N47 O47 H47 109.5 . . ? N48 C48 C47 177.6(9) . . ? 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 C19 N11 C12 N13 -1.4(8) . . . . ? C38 N11 C12 N13 -175.5(6) . . . . ? N11 C12 N13 C14 1.4(8) . . . . ? C12 N13 C14 C15 179.4(7) . . . . ? C12 N13 C14 C19 -0.8(8) . . . . ? C19 C14 C15 C16 -3.6(10) . . . . ? N13 C14 C15 C16 176.2(7) . . . . ? C14 C15 C16 C17 3.9(10) . . . . ? C14 C15 C16 C20 -177.6(6) . . . . ? C15 C16 C17 C18 -2.7(10) . . . . ? C20 C16 C17 C18 178.8(6) . . . . ? C15 C16 C17 C21 178.6(6) . . . . ? C20 C16 C17 C21 0.0(10) . . . . ? C16 C17 C18 C19 1.2(10) . . . . ? C21 C17 C18 C19 179.9(6) . . . . ? C12 N11 C19 C18 178.2(7) . . . . ? C38 N11 C19 C18 -7.9(12) . . . . ? C12 N11 C19 C14 0.8(7) . . . . ? C38 N11 C19 C14 174.7(6) . . . . ? C17 C18 C19 N11 -177.9(7) . . . . ? C17 C18 C19 C14 -0.9(10) . . . . ? C15 C14 C19 N11 179.8(6) . . . . ? N13 C14 C19 N11 0.0(7) . . . . ? C15 C14 C19 C18 2.1(10) . . . . ? N13 C14 C19 C18 -177.7(6) . . . . ? C36 C31 C32 C33 -1.1(10) . . . . ? C37 C31 C32 C33 179.0(6) . . . . ? C31 C32 C33 C34 2.7(9) . . . . ? C31 C32 C33 C38 -179.2(6) . . . . ? C32 C33 C34 C35 -2.7(10) . . . . ? C38 C33 C34 C35 179.2(6) . . . . ? C33 C34 C35 C36 1.0(11) . . . . ? C32 C31 C36 C35 -0.6(10) . . . . ? C37 C31 C36 C35 179.2(7) . . . . ? C34 C35 C36 C31 0.7(11) . . . . ? C12 N11 C38 C33 101.6(8) . . . . ? C19 N11 C38 C33 -71.1(8) . . . . ? C32 C33 C38 N11 128.6(6) . . . . ? C34 C33 C38 N11 -53.4(8) . . . . ? C46 C41 C42 C43 -2.9(10) . . . . ? C47 C41 C42 C43 176.1(6) . . . . ? C41 C42 C43 C44 3.5(10) . . . . ? C42 C43 C44 C45 -2.2(11) . . . . ? C42 C43 C44 Br1 -179.8(5) . . . . ? C43 C44 C45 C46 0.2(11) . . . . ? Br1 C44 C45 C46 177.9(5) . . . . ? C44 C45 C46 C41 0.5(11) . . . . ? C42 C41 C46 C45 0.9(10) . . . . ? C47 C41 C46 C45 -178.1(7) . . . . ? C42 C41 C47 N47 -3.9(10) . . . . ? C46 C41 C47 N47 175.1(6) . . . . ? C42 C41 C47 C48 177.8(6) . . . . ? C46 C41 C47 C48 -3.2(10) . . . . ? C41 C47 N47 O47 -178.8(5) . . . . ? C48 C47 N47 O47 -0.5(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O47 H47 N13 0.84 1.83 2.656(7) 167.3 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.789 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.157 #END data_B5 _database_code_depnum_ccdc_archive 'CCDC 694152' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [2-fluoro-PhC(CN)(=NOH)]2, 1,2-di(4-pyridyl)ethene ; _chemical_name_common '(2-fluoro-PhC(CN)(=NOH))2, 1,2-di(4-pyridyl)ethene' _chemical_melting_point ? _chemical_formula_moiety ; (C8 H5 N2 O F)2 (C12 H10 N2) ; _chemical_formula_sum 'C28 H20 F2 N6 O2' _chemical_formula_weight 510.50 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' F F 0.0171 0.0103 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.8189(6) _cell_length_b 11.2941(18) _cell_length_c 14.107(2) _cell_angle_alpha 98.884(10) _cell_angle_beta 93.147(11) _cell_angle_gamma 94.624(10) _cell_volume 597.79(16) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 783 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 26.70 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4295 _diffrn_reflns_av_R_equivalents 0.1106 _diffrn_reflns_av_sigmaI/netI 0.0972 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2606 _reflns_number_gt 1734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1000P)^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 2606 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1754 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 C11 C 0.9413(5) 0.26002(18) 0.58790(14) 0.0299(5) Uani 1 1 d . . . C12A C 1.1167(5) 0.3527(2) 0.55049(16) 0.0365(5) Uani 0.669(2) 1 d P A 1 F12 F 1.2186(6) 0.45468(18) 0.60662(15) 0.0501(5) Uani 0.669(2) 1 d P A 1 C12B C 1.1167(5) 0.3527(2) 0.55049(16) 0.0365(5) Uani 0.331(2) 1 d P A 2 H12 H 1.1889 0.4261 0.5921 0.044 Uiso 0.331(2) 1 calc PR A 2 C13 C 1.1896(6) 0.3426(2) 0.45607(17) 0.0442(6) Uani 1 1 d . . . H13 H 1.3081 0.4083 0.4326 0.053 Uiso 1 1 calc R A 1 C14 C 1.0892(6) 0.2360(3) 0.39513(17) 0.0478(6) Uani 1 1 d . A . H14 H 1.1426 0.2277 0.3296 0.057 Uiso 1 1 calc R . . C15 C 0.9126(6) 0.1416(2) 0.42864(16) 0.0453(6) Uani 1 1 d . . . H15 H 0.8397 0.0687 0.3865 0.054 Uiso 1 1 calc R A 1 C16A C 0.8432(5) 0.1545(2) 0.52396(16) 0.0378(5) Uani 0.669(2) 1 d P A 1 H16 H 0.7236 0.0888 0.5471 0.045 Uiso 0.669(2) 1 calc PR A 1 C16B C 0.8432(5) 0.1545(2) 0.52396(16) 0.0378(5) Uani 0.331(2) 1 d P A 2 F16 F 0.6496(11) 0.0710(4) 0.5501(3) 0.0501(5) Uani 0.331(2) 1 d P A 2 C17 C 0.8569(5) 0.27048(18) 0.68908(14) 0.0315(5) Uani 1 1 d . A . N17 N 0.8017(4) 0.37374(17) 0.73653(12) 0.0365(5) Uani 1 1 d . . . O17 O 0.7233(4) 0.36743(16) 0.82888(11) 0.0442(4) Uani 1 1 d . A . H17 H 0.675(7) 0.455(3) 0.851(2) 0.066(9) Uiso 1 1 d . . . C18 C 0.8337(6) 0.1630(2) 0.73340(16) 0.0428(6) Uani 1 1 d . . . N18 N 0.8214(8) 0.0771(2) 0.76621(17) 0.0707(8) Uani 1 1 d . A . N21 N 0.6016(5) 0.59158(17) 0.88855(13) 0.0390(5) Uani 1 1 d . . . C22 C 0.4607(6) 0.6538(2) 0.82510(16) 0.0424(6) Uani 1 1 d . . . H22 H 0.3870 0.6126 0.7624 0.051 Uiso 1 1 calc R . . C23 C 0.4173(6) 0.7738(2) 0.84592(15) 0.0387(5) Uani 1 1 d . . . H23 H 0.3183 0.8137 0.7977 0.046 Uiso 1 1 calc R . . C24 C 0.5165(5) 0.83774(19) 0.93681(14) 0.0314(5) Uani 1 1 d . . . C25 C 0.6635(5) 0.7723(2) 1.00309(15) 0.0358(5) Uani 1 1 d . . . H25 H 0.7371 0.8109 1.0666 0.043 Uiso 1 1 calc R . . C26 C 0.7011(6) 0.6522(2) 0.97607(15) 0.0363(5) Uani 1 1 d . . . H26 H 0.8036 0.6098 1.0222 0.044 Uiso 1 1 calc R . . C27 C 0.4593(5) 0.96438(19) 0.95824(15) 0.0337(5) Uani 1 1 d . . . H27 H 0.3542 0.9993 0.9079 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0273(9) 0.0332(11) 0.0295(11) 0.0039(8) 0.0016(7) 0.0063(8) C12A 0.0344(11) 0.0390(13) 0.0367(12) 0.0079(9) -0.0001(8) 0.0043(9) F12 0.0647(12) 0.0328(10) 0.0493(11) 0.0049(8) -0.0004(9) -0.0102(8) C12B 0.0344(11) 0.0390(13) 0.0367(12) 0.0079(9) -0.0001(8) 0.0043(9) C13 0.0372(12) 0.0566(16) 0.0421(13) 0.0192(11) 0.0027(9) 0.0028(10) C14 0.0375(12) 0.0795(19) 0.0276(11) 0.0085(12) 0.0015(9) 0.0133(11) C15 0.0431(12) 0.0540(15) 0.0342(12) -0.0087(11) -0.0023(9) 0.0103(11) C16A 0.0353(11) 0.0398(13) 0.0357(12) -0.0001(9) 0.0000(8) 0.0021(9) C16B 0.0353(11) 0.0398(13) 0.0357(12) -0.0001(9) 0.0000(8) 0.0021(9) F16 0.0647(12) 0.0328(10) 0.0493(11) 0.0049(8) -0.0004(9) -0.0102(8) C17 0.0328(10) 0.0310(11) 0.0303(11) 0.0034(8) 0.0003(8) 0.0044(8) N17 0.0411(10) 0.0389(11) 0.0292(10) 0.0011(8) 0.0036(7) 0.0087(8) O17 0.0623(10) 0.0428(10) 0.0282(8) 0.0014(7) 0.0093(7) 0.0123(8) C18 0.0584(14) 0.0396(14) 0.0306(12) 0.0015(10) 0.0100(10) 0.0082(10) N18 0.126(2) 0.0454(15) 0.0464(14) 0.0152(11) 0.0276(14) 0.0151(14) N21 0.0428(10) 0.0374(11) 0.0355(10) -0.0007(8) 0.0080(8) 0.0048(8) C22 0.0500(13) 0.0450(14) 0.0286(12) -0.0037(10) 0.0026(9) 0.0018(10) C23 0.0421(12) 0.0426(13) 0.0304(12) 0.0033(9) -0.0007(8) 0.0041(9) C24 0.0299(10) 0.0364(12) 0.0276(10) 0.0039(8) 0.0066(7) 0.0008(8) C25 0.0380(11) 0.0417(13) 0.0263(11) 0.0009(9) 0.0025(8) 0.0031(9) C26 0.0416(11) 0.0368(12) 0.0309(11) 0.0051(9) 0.0058(8) 0.0035(9) C27 0.0341(10) 0.0386(12) 0.0289(11) 0.0068(8) 0.0025(8) 0.0034(8) _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 C11 C12A 1.385(3) . ? C11 C16A 1.391(3) . ? C11 C17 1.470(3) . ? C12A F12 1.310(3) . ? C12A C13 1.365(3) . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.374(4) . ? C14 H14 0.9500 . ? C15 C16A 1.373(3) . ? C15 H15 0.9500 . ? C16A H16 0.9500 . ? C17 N17 1.291(3) . ? C17 C18 1.447(3) . ? N17 O17 1.364(2) . ? O17 H17 1.03(3) . ? C18 N18 1.136(3) . ? N21 C26 1.335(3) . ? N21 C22 1.337(3) . ? C22 C23 1.367(3) . ? C22 H22 0.9500 . ? C23 C24 1.388(3) . ? C23 H23 0.9500 . ? C24 C25 1.399(3) . ? C24 C27 1.452(3) . ? C25 C26 1.373(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C27 1.326(4) 2_677 ? C27 H27 0.9500 . ? 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 C12A C11 C16A 116.4(2) . . ? C12A C11 C17 122.95(18) . . ? C16A C11 C17 120.66(19) . . ? F12 C12A C13 117.7(2) . . ? F12 C12A C11 119.8(2) . . ? C13 C12A C11 122.5(2) . . ? C12A C13 C14 119.2(2) . . ? C12A C13 H13 120.4 . . ? C14 C13 H13 120.4 . . ? C15 C14 C13 120.5(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16A C15 C14 118.9(2) . . ? C16A C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16A C11 122.5(2) . . ? C15 C16A H16 118.8 . . ? C11 C16A H16 118.8 . . ? N17 C17 C18 121.17(19) . . ? N17 C17 C11 120.14(19) . . ? C18 C17 C11 118.69(18) . . ? C17 N17 O17 112.64(18) . . ? N17 O17 H17 99.6(16) . . ? N18 C18 C17 178.0(3) . . ? C26 N21 C22 116.81(19) . . ? N21 C22 C23 123.3(2) . . ? N21 C22 H22 118.4 . . ? C23 C22 H22 118.4 . . ? C22 C23 C24 120.6(2) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C25 116.0(2) . . ? C23 C24 C27 119.74(19) . . ? C25 C24 C27 124.27(19) . . ? C26 C25 C24 119.76(19) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? N21 C26 C25 123.6(2) . . ? N21 C26 H26 118.2 . . ? C25 C26 H26 118.2 . . ? C27 C27 C24 125.9(3) 2_677 . ? C27 C27 H27 117.1 2_677 . ? C24 C27 H27 117.1 . . ? 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 C16A C11 C12A F12 -179.7(2) . . . . ? C17 C11 C12A F12 0.9(3) . . . . ? C16A C11 C12A C13 0.3(3) . . . . ? C17 C11 C12A C13 -179.09(19) . . . . ? F12 C12A C13 C14 179.3(2) . . . . ? C11 C12A C13 C14 -0.7(3) . . . . ? C12A C13 C14 C15 1.1(3) . . . . ? C13 C14 C15 C16A -1.1(4) . . . . ? C14 C15 C16A C11 0.8(3) . . . . ? C12A C11 C16A C15 -0.4(3) . . . . ? C17 C11 C16A C15 179.1(2) . . . . ? C12A C11 C17 N17 29.8(3) . . . . ? C16A C11 C17 N17 -149.6(2) . . . . ? C12A C11 C17 C18 -150.8(2) . . . . ? C16A C11 C17 C18 29.8(3) . . . . ? C18 C17 N17 O17 0.0(3) . . . . ? C11 C17 N17 O17 179.37(16) . . . . ? C26 N21 C22 C23 0.2(3) . . . . ? N21 C22 C23 C24 -0.8(4) . . . . ? C22 C23 C24 C25 0.7(3) . . . . ? C22 C23 C24 C27 -178.3(2) . . . . ? C23 C24 C25 C26 -0.1(3) . . . . ? C27 C24 C25 C26 178.9(2) . . . . ? C22 N21 C26 C25 0.5(3) . . . . ? C24 C25 C26 N21 -0.5(3) . . . . ? C23 C24 C27 C27 179.8(3) . . . 2_677 ? C25 C24 C27 C27 0.9(4) . . . 2_677 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O17 H17 N21 1.03(3) 1.60(3) 2.628(3) 178(3) . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.295 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.070 #END data_C6 _database_code_depnum_ccdc_archive 'CCDC 694153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 481 1,4-di[(1-benzimidazolyl)methyl]benzene, [3-chloro-PhC(CN)(=NOH)]2 ; _chemical_name_common ;481 1,4-di((1-benzimidazolyl)methyl)benzene, (3-chloro- PhC(CN)(=NOH))2 ; _chemical_melting_point ? _chemical_formula_moiety ; (C22 H18 N4) (C8 H5 N2 O Cl)2 ; _chemical_formula_sum 'C38 H28 Cl2 N8 O2' _chemical_formula_weight 699.58 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 13.6335(10) _cell_length_b 4.4402(3) _cell_length_c 27.297(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.084(3) _cell_angle_gamma 90.00 _cell_volume 1648.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9905 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 30.52 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9297 _exptl_absorpt_correction_T_max 0.9639 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40395 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 30.99 _reflns_number_total 5259 _reflns_number_gt 3883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^2^+0.4000P] 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 5259 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0634 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1118 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Cl1 Cl 0.15560(2) -0.38771(8) 0.668525(14) 0.03458(11) Uani 1 1 d . . . N11 N 0.81489(7) 1.1873(2) 0.58747(4) 0.0182(2) Uani 1 1 d . . . C12 C 0.72093(9) 1.1275(3) 0.57020(5) 0.0214(3) Uani 1 1 d . . . H12 H 0.6906 1.2177 0.5414 0.026 Uiso 1 1 calc R . . N13 N 0.67622(8) 0.9328(2) 0.59718(4) 0.0233(2) Uani 1 1 d . . . C14 C 0.74478(9) 0.8585(3) 0.63534(5) 0.0204(2) Uani 1 1 d . . . C15 C 0.73689(10) 0.6647(3) 0.67527(5) 0.0256(3) Uani 1 1 d . . . H15 H 0.6777 0.5586 0.6798 0.031 Uiso 1 1 calc R . . C16 C 0.81842(11) 0.6334(3) 0.70785(5) 0.0277(3) Uani 1 1 d . . . H16 H 0.8150 0.5043 0.7354 0.033 Uiso 1 1 calc R . . C17 C 0.90642(11) 0.7882(3) 0.70114(5) 0.0270(3) Uani 1 1 d . . . H17 H 0.9612 0.7591 0.7242 0.032 Uiso 1 1 calc R . . C18 C 0.91557(10) 0.9816(3) 0.66199(5) 0.0232(3) Uani 1 1 d . . . H18 H 0.9750 1.0865 0.6576 0.028 Uiso 1 1 calc R . . C19 C 0.83288(9) 1.0142(2) 0.62942(4) 0.0189(2) Uani 1 1 d . . . C21 C 0.94631(9) 1.1832(2) 0.53029(4) 0.0178(2) Uani 1 1 d . . . C22 C 0.90590(9) 1.0914(3) 0.48470(5) 0.0237(3) Uani 1 1 d . . . H22 H 0.8413 1.1537 0.4739 0.028 Uiso 1 1 calc R . . C26 C 1.04110(9) 1.0909(3) 0.54535(5) 0.0241(3) Uani 1 1 d . . . H26 H 1.0699 1.1528 0.5764 0.029 Uiso 1 1 calc R . . C27 C 0.88620(9) 1.3722(2) 0.56318(5) 0.0194(2) Uani 1 1 d . . . H27A H 0.9306 1.4729 0.5884 0.023 Uiso 1 1 calc R . . H27B H 0.8509 1.5303 0.5434 0.023 Uiso 1 1 calc R . . C31 C 0.39381(9) 0.0837(2) 0.63858(5) 0.0192(2) Uani 1 1 d . . . C32 C 0.29964(9) -0.0411(3) 0.63599(5) 0.0213(2) Uani 1 1 d . . . H32 H 0.2532 0.0096 0.6097 0.026 Uiso 1 1 calc R . . C33 C 0.27460(9) -0.2398(3) 0.67222(5) 0.0235(3) Uani 1 1 d . . . C34 C 0.34031(11) -0.3196(3) 0.71095(5) 0.0271(3) Uani 1 1 d . . . H34 H 0.3218 -0.4550 0.7356 0.033 Uiso 1 1 calc R . . C35 C 0.43433(10) -0.1962(3) 0.71281(5) 0.0274(3) Uani 1 1 d . . . H35 H 0.4807 -0.2497 0.7390 0.033 Uiso 1 1 calc R . . C36 C 0.46150(10) 0.0026(3) 0.67731(5) 0.0239(3) Uani 1 1 d . . . H36 H 0.5261 0.0843 0.6792 0.029 Uiso 1 1 calc R . . C37 C 0.42049(9) 0.2999(3) 0.60091(5) 0.0196(2) Uani 1 1 d . . . N37 N 0.50121(8) 0.4531(2) 0.60675(4) 0.0223(2) Uani 1 1 d . . . O37 O 0.51284(7) 0.6451(2) 0.56870(3) 0.0260(2) Uani 1 1 d . . . H37 H 0.5728(12) 0.749(4) 0.5792(5) 0.031 Uiso 1 1 d . . . C38 C 0.35289(9) 0.3460(3) 0.55810(5) 0.0234(3) Uani 1 1 d . . . N38 N 0.29706(9) 0.3799(3) 0.52529(5) 0.0340(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.02735(19) 0.03709(18) 0.0403(2) 0.00639(15) 0.00937(15) -0.00522(14) N11 0.0183(5) 0.0189(4) 0.0177(5) 0.0003(4) 0.0032(4) -0.0001(4) C12 0.0193(6) 0.0229(5) 0.0222(6) 0.0001(5) 0.0023(5) 0.0013(4) N13 0.0195(5) 0.0258(5) 0.0251(6) 0.0012(4) 0.0043(4) -0.0002(4) C14 0.0221(6) 0.0186(5) 0.0211(6) -0.0025(4) 0.0071(5) 0.0012(4) C15 0.0298(7) 0.0216(5) 0.0268(7) 0.0002(5) 0.0116(5) 0.0000(5) C16 0.0404(8) 0.0232(6) 0.0205(7) 0.0030(5) 0.0084(6) 0.0043(5) C17 0.0340(7) 0.0249(6) 0.0217(7) -0.0005(5) -0.0016(5) 0.0046(5) C18 0.0241(6) 0.0219(5) 0.0236(7) -0.0028(5) 0.0015(5) 0.0005(5) C19 0.0222(6) 0.0171(5) 0.0179(6) -0.0023(4) 0.0056(5) 0.0018(4) C21 0.0186(6) 0.0158(5) 0.0194(6) 0.0017(4) 0.0043(4) -0.0032(4) C22 0.0170(6) 0.0316(6) 0.0222(7) -0.0017(5) -0.0005(5) 0.0025(5) C26 0.0217(6) 0.0309(6) 0.0195(6) -0.0054(5) -0.0006(5) 0.0000(5) C27 0.0212(6) 0.0170(5) 0.0202(6) 0.0001(4) 0.0038(5) -0.0020(4) C31 0.0203(6) 0.0180(5) 0.0193(6) -0.0020(4) 0.0017(5) 0.0025(4) C32 0.0209(6) 0.0218(5) 0.0212(6) -0.0010(5) 0.0021(5) 0.0032(4) C33 0.0250(6) 0.0223(5) 0.0240(7) -0.0013(5) 0.0062(5) 0.0010(5) C34 0.0381(8) 0.0238(6) 0.0198(6) 0.0012(5) 0.0047(6) 0.0014(5) C35 0.0362(8) 0.0248(6) 0.0201(7) -0.0004(5) -0.0050(5) 0.0040(5) C36 0.0254(6) 0.0213(5) 0.0241(7) -0.0025(5) -0.0037(5) 0.0015(5) C37 0.0188(6) 0.0202(5) 0.0197(6) -0.0003(4) 0.0002(5) 0.0021(4) N37 0.0209(5) 0.0217(5) 0.0245(6) -0.0010(4) 0.0037(4) 0.0013(4) O37 0.0236(5) 0.0293(4) 0.0252(5) 0.0038(4) 0.0018(4) -0.0053(4) C38 0.0216(6) 0.0243(6) 0.0244(7) 0.0041(5) 0.0025(5) -0.0031(5) N38 0.0307(6) 0.0401(7) 0.0302(7) 0.0102(5) -0.0048(5) -0.0060(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C33 1.7465(13) . ? N11 C12 1.3594(16) . ? N11 C19 1.3863(15) . ? N11 C27 1.4666(15) . ? C12 N13 1.3135(16) . ? C12 H12 0.9500 . ? N13 C14 1.3887(17) . ? C14 C15 1.3990(17) . ? C14 C19 1.4051(17) . ? C15 C16 1.380(2) . ? C15 H15 0.9500 . ? C16 C17 1.406(2) . ? C16 H16 0.9500 . ? C17 C18 1.3836(18) . ? C17 H17 0.9500 . ? C18 C19 1.3926(18) . ? C18 H18 0.9500 . ? C21 C22 1.3857(18) . ? C21 C26 1.3897(17) . ? C21 C27 1.5123(16) . ? C22 C26 1.3911(17) 3_776 ? C22 H22 0.9500 . ? C26 C22 1.3911(17) 3_776 ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C32 1.3954(17) . ? C31 C36 1.4001(17) . ? C31 C37 1.4711(17) . ? C32 C33 1.3859(17) . ? C32 H32 0.9500 . ? C33 C34 1.3823(19) . ? C34 C35 1.392(2) . ? C34 H34 0.9500 . ? C35 C36 1.3806(19) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N37 1.2939(16) . ? C37 C38 1.4504(18) . ? N37 O37 1.3618(14) . ? O37 H37 0.965(16) . ? C38 N38 1.1433(17) . ? 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 C12 N11 C19 106.57(10) . . ? C12 N11 C27 126.24(10) . . ? C19 N11 C27 126.86(10) . . ? N13 C12 N11 113.42(11) . . ? N13 C12 H12 123.3 . . ? N11 C12 H12 123.3 . . ? C12 N13 C14 105.22(10) . . ? N13 C14 C15 130.20(12) . . ? N13 C14 C19 109.40(11) . . ? C15 C14 C19 120.40(12) . . ? C16 C15 C14 117.45(12) . . ? C16 C15 H15 121.3 . . ? C14 C15 H15 121.3 . . ? C15 C16 C17 121.49(12) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 121.93(13) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C17 C18 C19 116.37(12) . . ? C17 C18 H18 121.8 . . ? C19 C18 H18 121.8 . . ? N11 C19 C18 132.25(11) . . ? N11 C19 C14 105.38(10) . . ? C18 C19 C14 122.36(11) . . ? C22 C21 C26 118.74(11) . . ? C22 C21 C27 119.91(11) . . ? C26 C21 C27 121.32(11) . . ? C21 C22 C26 120.71(11) . 3_776 ? C21 C22 H22 119.6 . . ? C26 C22 H22 119.6 3_776 . ? C21 C26 C22 120.55(12) . 3_776 ? C21 C26 H26 119.7 . . ? C22 C26 H26 119.7 3_776 . ? N11 C27 C21 111.25(9) . . ? N11 C27 H27A 109.4 . . ? C21 C27 H27A 109.4 . . ? N11 C27 H27B 109.4 . . ? C21 C27 H27B 109.4 . . ? H27A C27 H27B 108.0 . . ? C32 C31 C36 119.39(11) . . ? C32 C31 C37 119.75(11) . . ? C36 C31 C37 120.87(11) . . ? C33 C32 C31 119.29(12) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C34 C33 C32 121.98(12) . . ? C34 C33 Cl1 119.77(10) . . ? C32 C33 Cl1 118.24(10) . . ? C33 C34 C35 118.17(12) . . ? C33 C34 H34 120.9 . . ? C35 C34 H34 120.9 . . ? C36 C35 C34 121.24(12) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C35 C36 C31 119.93(12) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? N37 C37 C38 120.74(11) . . ? N37 C37 C31 120.49(11) . . ? C38 C37 C31 118.72(10) . . ? C37 N37 O37 112.30(10) . . ? N37 O37 H37 102.4(9) . . ? N38 C38 C37 177.71(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 C19 N11 C12 N13 0.27(14) . . . . ? C27 N11 C12 N13 174.02(10) . . . . ? N11 C12 N13 C14 0.41(14) . . . . ? C12 N13 C14 C15 179.04(12) . . . . ? C12 N13 C14 C19 -0.93(13) . . . . ? N13 C14 C15 C16 179.78(12) . . . . ? C19 C14 C15 C16 -0.26(18) . . . . ? C14 C15 C16 C17 -0.45(19) . . . . ? C15 C16 C17 C18 0.7(2) . . . . ? C16 C17 C18 C19 -0.19(19) . . . . ? C12 N11 C19 C18 179.57(13) . . . . ? C27 N11 C19 C18 5.9(2) . . . . ? C12 N11 C19 C14 -0.82(12) . . . . ? C27 N11 C19 C14 -174.51(10) . . . . ? C17 C18 C19 N11 179.02(12) . . . . ? C17 C18 C19 C14 -0.54(18) . . . . ? N13 C14 C19 N11 1.09(13) . . . . ? C15 C14 C19 N11 -178.88(10) . . . . ? N13 C14 C19 C18 -179.25(11) . . . . ? C15 C14 C19 C18 0.78(18) . . . . ? C26 C21 C22 C26 0.3(2) . . . 3_776 ? C27 C21 C22 C26 -177.82(11) . . . 3_776 ? C22 C21 C26 C22 -0.3(2) . . . 3_776 ? C27 C21 C26 C22 177.79(11) . . . 3_776 ? C12 N11 C27 C21 -90.67(14) . . . . ? C19 N11 C27 C21 81.83(14) . . . . ? C22 C21 C27 N11 77.61(14) . . . . ? C26 C21 C27 N11 -100.49(13) . . . . ? C36 C31 C32 C33 0.87(17) . . . . ? C37 C31 C32 C33 -178.68(11) . . . . ? C31 C32 C33 C34 -0.22(18) . . . . ? C31 C32 C33 Cl1 179.00(9) . . . . ? C32 C33 C34 C35 -0.48(19) . . . . ? Cl1 C33 C34 C35 -179.70(10) . . . . ? C33 C34 C35 C36 0.54(19) . . . . ? C34 C35 C36 C31 0.10(19) . . . . ? C32 C31 C36 C35 -0.81(18) . . . . ? C37 C31 C36 C35 178.73(11) . . . . ? C32 C31 C37 N37 169.05(11) . . . . ? C36 C31 C37 N37 -10.49(17) . . . . ? C32 C31 C37 C38 -8.65(17) . . . . ? C36 C31 C37 C38 171.81(11) . . . . ? C38 C37 N37 O37 -1.28(16) . . . . ? C31 C37 N37 O37 -178.93(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O37 H37 N13 0.965(16) 1.672(16) 2.6365(14) 179.5(17) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.337 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.055 #END data_D7 _database_code_depnum_ccdc_archive 'CCDC 694154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; MS 512 1-(4-pyridylmethyl)-5,6-Me2benzimidazole, 4-F-PhC(CN)(NOH) ; _chemical_name_common ;MS 512 1-(4-pyridylmethyl)-5,6-Me2benzimidazole, 4-F- PhC(CN)(NOH) ; _chemical_melting_point ? _chemical_formula_moiety ; (C15 H15 N3) (C8 H5 N2 O F) ; _chemical_formula_sum 'C23 H20 F N5 O' _chemical_formula_weight 401.44 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' 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 P2(1)/n 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 16.1659(12) _cell_length_b 6.4146(5) _cell_length_c 21.0074(16) _cell_angle_alpha 90.00 _cell_angle_beta 105.945(5) _cell_angle_gamma 90.00 _cell_volume 2094.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2093 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 21.51 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20522 _diffrn_reflns_av_R_equivalents 0.0654 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 30.50 _reflns_number_total 6367 _reflns_number_gt 2616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0500P)^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 6367 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1597 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _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 N11 N 0.37443(5) -0.11599(11) 0.66110(4) 0.0433(2) Uani 1 1 d . . . C12 C 0.33642(6) 0.04439(15) 0.68356(5) 0.0471(3) Uani 1 1 d . . . H12 H 0.3285 0.0481 0.7267 0.056 Uiso 1 1 calc R . . N13 N 0.31126(5) 0.19532(12) 0.64008(4) 0.0473(2) Uani 1 1 d . . . C14 C 0.33472(5) 0.12780(14) 0.58411(4) 0.0415(3) Uani 1 1 d . . . C15 C 0.32266(6) 0.22021(16) 0.52226(5) 0.0514(3) Uani 1 1 d . . . H15 H 0.2968 0.3539 0.5136 0.062 Uiso 1 1 calc R . . C16 C 0.34871(6) 0.11554(17) 0.47375(5) 0.0562(3) Uani 1 1 d . . . C17 C 0.38679(6) -0.08472(17) 0.48665(5) 0.0577(3) Uani 1 1 d . . . C18 C 0.39997(6) -0.17632(16) 0.54824(5) 0.0523(3) Uani 1 1 d . . . H18 H 0.4262 -0.3096 0.5574 0.063 Uiso 1 1 calc R . . C19 C 0.37353(5) -0.06661(14) 0.59649(4) 0.0410(3) Uani 1 1 d . . . C20 C 0.33338(8) 0.2124(2) 0.40594(5) 0.0862(5) Uani 1 1 d . . . H20A H 0.3042 0.3467 0.4050 0.129 Uiso 1 1 calc R . . H20B H 0.2974 0.1193 0.3727 0.129 Uiso 1 1 calc R . . H20C H 0.3886 0.2341 0.3962 0.129 Uiso 1 1 calc R . . C21 C 0.41269(8) -0.2031(2) 0.43241(6) 0.0892(4) Uani 1 1 d . . . H21A H 0.4373 -0.3382 0.4496 0.134 Uiso 1 1 calc R . . H21B H 0.4556 -0.1221 0.4178 0.134 Uiso 1 1 calc R . . H21C H 0.3619 -0.2252 0.3949 0.134 Uiso 1 1 calc R . . N31 N 0.68684(5) -0.32521(13) 0.76207(4) 0.0563(3) Uani 1 1 d . . . C32 C 0.64314(6) -0.15064(16) 0.76540(5) 0.0563(3) Uani 1 1 d . . . H32 H 0.6750 -0.0294 0.7829 0.068 Uiso 1 1 calc R . . C33 C 0.55466(6) -0.13526(15) 0.74501(5) 0.0514(3) Uani 1 1 d . . . H33 H 0.5272 -0.0070 0.7491 0.062 Uiso 1 1 calc R . . C34 C 0.50646(6) -0.30795(14) 0.71862(4) 0.0422(3) Uani 1 1 d . . . C35 C 0.55086(6) -0.48934(15) 0.71461(5) 0.0486(3) Uani 1 1 d . . . H35 H 0.5205 -0.6123 0.6967 0.058 Uiso 1 1 calc R . . C36 C 0.63954(6) -0.49095(16) 0.73674(5) 0.0528(3) Uani 1 1 d . . . H36 H 0.6686 -0.6178 0.7337 0.063 Uiso 1 1 calc R . . C37 C 0.40955(6) -0.30432(15) 0.69737(5) 0.0553(3) Uani 1 1 d . . . H37A H 0.3884 -0.4272 0.6690 0.066 Uiso 1 1 calc R . . H37B H 0.3881 -0.3156 0.7371 0.066 Uiso 1 1 calc R . . C41 C 0.13292(6) 0.91448(15) 0.53062(5) 0.0456(3) Uani 1 1 d . . . C42 C 0.14710(7) 0.84566(17) 0.47162(5) 0.0598(3) Uani 1 1 d . . . H42 H 0.1680 0.7084 0.4689 0.072 Uiso 1 1 calc R . . C43 C 0.13117(8) 0.97458(19) 0.41720(6) 0.0742(4) Uani 1 1 d . . . H43 H 0.1400 0.9269 0.3768 0.089 Uiso 1 1 calc R . . C44 C 0.10243(7) 1.17263(19) 0.42246(6) 0.0715(4) Uani 1 1 d . . . F44 F 0.08974(6) 1.30271(13) 0.36980(4) 0.1130(3) Uani 1 1 d . . . C45 C 0.08562(7) 1.24501(18) 0.47903(6) 0.0676(4) Uani 1 1 d . . . H45 H 0.0638 1.3817 0.4809 0.081 Uiso 1 1 calc R . . C46 C 0.10121(6) 1.11440(15) 0.53333(5) 0.0545(3) Uani 1 1 d . . . H46 H 0.0901 1.1620 0.5730 0.065 Uiso 1 1 calc R . . C47 C 0.15244(6) 0.77931(14) 0.58945(4) 0.0445(3) Uani 1 1 d . . . N47 N 0.19656(5) 0.61060(12) 0.59205(4) 0.0495(2) Uani 1 1 d . . . O47 O 0.20808(4) 0.50451(10) 0.65082(3) 0.0562(2) Uani 1 1 d . . . H47 H 0.2506(6) 0.3834(15) 0.6487(5) 0.067 Uiso 1 1 d . . . C48 C 0.12258(7) 0.83896(16) 0.64544(5) 0.0574(3) Uani 1 1 d . . . N48 N 0.09860(7) 0.88476(17) 0.69001(5) 0.0932(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 N11 0.0405(4) 0.0372(4) 0.0497(4) 0.0044(4) 0.0082(3) 0.0027(3) C12 0.0447(5) 0.0486(5) 0.0457(5) -0.0027(5) 0.0088(4) 0.0014(4) N13 0.0496(4) 0.0418(4) 0.0482(4) -0.0013(4) 0.0093(4) 0.0067(4) C14 0.0382(5) 0.0383(5) 0.0449(5) -0.0020(4) 0.0058(4) -0.0001(4) C15 0.0465(5) 0.0494(6) 0.0532(6) 0.0086(5) 0.0050(5) -0.0041(5) C16 0.0511(5) 0.0686(7) 0.0469(5) -0.0012(5) 0.0103(5) -0.0150(5) C17 0.0495(5) 0.0699(7) 0.0569(6) -0.0180(5) 0.0202(5) -0.0171(5) C18 0.0460(5) 0.0451(5) 0.0672(6) -0.0125(5) 0.0178(5) -0.0023(4) C19 0.0362(4) 0.0392(5) 0.0455(5) -0.0019(4) 0.0079(4) -0.0033(4) C20 0.0894(8) 0.1145(10) 0.0534(6) 0.0116(7) 0.0172(6) -0.0243(8) C21 0.0918(8) 0.1047(9) 0.0829(7) -0.0399(7) 0.0436(6) -0.0257(7) N31 0.0462(4) 0.0614(5) 0.0612(5) 0.0049(4) 0.0146(4) 0.0033(4) C32 0.0483(5) 0.0515(6) 0.0654(6) -0.0029(5) 0.0093(5) -0.0075(5) C33 0.0492(5) 0.0391(5) 0.0645(6) -0.0012(5) 0.0129(5) 0.0016(4) C34 0.0437(5) 0.0365(5) 0.0452(5) 0.0088(4) 0.0105(4) 0.0003(4) C35 0.0521(5) 0.0380(5) 0.0536(6) 0.0039(5) 0.0112(5) -0.0018(4) C36 0.0535(5) 0.0489(6) 0.0576(6) 0.0050(5) 0.0179(5) 0.0100(5) C37 0.0470(5) 0.0427(5) 0.0711(6) 0.0157(5) 0.0080(5) 0.0000(5) C41 0.0399(5) 0.0460(5) 0.0477(5) -0.0056(5) 0.0067(4) -0.0056(4) C42 0.0684(6) 0.0574(6) 0.0543(6) -0.0060(5) 0.0181(5) -0.0062(5) C43 0.0905(8) 0.0764(8) 0.0576(6) -0.0001(6) 0.0237(6) -0.0146(7) C44 0.0702(7) 0.0743(7) 0.0632(7) 0.0212(6) 0.0066(6) -0.0143(6) F44 0.1365(6) 0.1061(5) 0.0901(5) 0.0462(4) 0.0203(5) -0.0134(5) C45 0.0591(6) 0.0544(6) 0.0813(8) 0.0095(6) 0.0059(6) -0.0017(5) C46 0.0479(5) 0.0508(6) 0.0608(6) -0.0030(5) 0.0083(5) -0.0018(5) C47 0.0403(5) 0.0440(5) 0.0466(5) -0.0096(5) 0.0075(4) 0.0026(4) N47 0.0477(4) 0.0487(5) 0.0513(4) -0.0028(4) 0.0126(4) 0.0009(4) O47 0.0600(4) 0.0537(4) 0.0567(4) 0.0013(3) 0.0188(3) 0.0153(3) C48 0.0663(6) 0.0550(6) 0.0471(5) -0.0047(5) 0.0090(5) 0.0196(5) N48 0.1238(8) 0.0988(7) 0.0602(6) -0.0052(6) 0.0305(6) 0.0465(6) _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 N11 C12 1.3481(12) . ? N11 C19 1.3900(12) . ? N11 C37 1.4576(12) . ? C12 N13 1.3165(12) . ? C12 H12 0.9500 . ? N13 C14 1.3996(12) . ? C14 C19 1.3880(12) . ? C14 C15 1.3922(13) . ? C15 C16 1.3792(15) . ? C15 H15 0.9500 . ? C16 C17 1.4181(15) . ? C16 C20 1.5109(15) . ? C17 C18 1.3831(15) . ? C17 C21 1.5207(17) . ? C18 C19 1.3942(14) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N31 C36 1.3321(12) . ? N31 C32 1.3361(13) . ? C32 C33 1.3794(13) . ? C32 H32 0.9500 . ? C33 C34 1.3800(13) . ? C33 H33 0.9500 . ? C34 C35 1.3818(13) . ? C34 C37 1.5066(13) . ? C35 C36 1.3803(13) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C41 C46 1.3880(14) . ? C41 C42 1.3928(15) . ? C41 C47 1.4711(13) . ? C42 C43 1.3768(15) . ? C42 H42 0.9500 . ? C43 C44 1.3675(17) . ? C43 H43 0.9500 . ? C44 F44 1.3555(13) . ? C44 C45 1.3708(17) . ? C45 C46 1.3816(15) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 N47 1.2889(12) . ? C47 C48 1.4406(15) . ? N47 O47 1.3769(10) . ? O47 H47 1.047(10) . ? C48 N48 1.1456(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C19 106.51(7) . . ? C12 N11 C37 126.81(9) . . ? C19 N11 C37 126.68(8) . . ? N13 C12 N11 113.71(9) . . ? N13 C12 H12 123.1 . . ? N11 C12 H12 123.1 . . ? C12 N13 C14 104.59(8) . . ? C19 C14 C15 119.85(9) . . ? C19 C14 N13 109.47(8) . . ? C15 C14 N13 130.65(8) . . ? C16 C15 C14 119.29(9) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C17 120.30(9) . . ? C15 C16 C20 119.48(10) . . ? C17 C16 C20 120.19(10) . . ? C18 C17 C16 120.72(10) . . ? C18 C17 C21 119.04(10) . . ? C16 C17 C21 120.24(10) . . ? C17 C18 C19 117.81(9) . . ? C17 C18 H18 121.1 . . ? C19 C18 H18 121.1 . . ? C14 C19 N11 105.71(8) . . ? C14 C19 C18 122.02(9) . . ? N11 C19 C18 132.22(8) . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C36 N31 C32 115.85(8) . . ? N31 C32 C33 124.18(9) . . ? N31 C32 H32 117.9 . . ? C33 C32 H32 117.9 . . ? C32 C33 C34 119.36(9) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C33 C34 C35 117.06(8) . . ? C33 C34 C37 122.21(9) . . ? C35 C34 C37 120.68(8) . . ? C36 C35 C34 119.65(9) . . ? C36 C35 H35 120.2 . . ? C34 C35 H35 120.2 . . ? N31 C36 C35 123.90(9) . . ? N31 C36 H36 118.1 . . ? C35 C36 H36 118.1 . . ? N11 C37 C34 113.06(8) . . ? N11 C37 H37A 109.0 . . ? C34 C37 H37A 109.0 . . ? N11 C37 H37B 109.0 . . ? C34 C37 H37B 109.0 . . ? H37A C37 H37B 107.8 . . ? C46 C41 C42 118.83(9) . . ? C46 C41 C47 120.44(9) . . ? C42 C41 C47 120.73(9) . . ? C43 C42 C41 120.64(10) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? C44 C43 C42 118.76(12) . . ? C44 C43 H43 120.6 . . ? C42 C43 H43 120.6 . . ? F44 C44 C43 118.98(11) . . ? F44 C44 C45 118.52(11) . . ? C43 C44 C45 122.50(11) . . ? C44 C45 C46 118.41(11) . . ? C44 C45 H45 120.8 . . ? C46 C45 H45 120.8 . . ? C45 C46 C41 120.81(11) . . ? C45 C46 H46 119.6 . . ? C41 C46 H46 119.6 . . ? N47 C47 C48 119.60(9) . . ? N47 C47 C41 121.27(9) . . ? C48 C47 C41 119.12(8) . . ? C47 N47 O47 112.96(8) . . ? N47 O47 H47 104.9(5) . . ? N48 C48 C47 179.44(13) . . ? 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 C19 N11 C12 N13 -0.54(10) . . . . ? C37 N11 C12 N13 179.49(8) . . . . ? N11 C12 N13 C14 0.10(10) . . . . ? C12 N13 C14 C19 0.39(9) . . . . ? C12 N13 C14 C15 178.29(9) . . . . ? C19 C14 C15 C16 0.73(13) . . . . ? N13 C14 C15 C16 -176.99(9) . . . . ? C14 C15 C16 C17 0.46(14) . . . . ? C14 C15 C16 C20 178.21(9) . . . . ? C15 C16 C17 C18 -1.30(15) . . . . ? C20 C16 C17 C18 -179.03(9) . . . . ? C15 C16 C17 C21 177.91(9) . . . . ? C20 C16 C17 C21 0.18(15) . . . . ? C16 C17 C18 C19 0.89(14) . . . . ? C21 C17 C18 C19 -178.33(9) . . . . ? C15 C14 C19 N11 -178.87(8) . . . . ? N13 C14 C19 N11 -0.70(9) . . . . ? C15 C14 C19 C18 -1.16(13) . . . . ? N13 C14 C19 C18 177.01(8) . . . . ? C12 N11 C19 C14 0.74(9) . . . . ? C37 N11 C19 C14 -179.30(8) . . . . ? C12 N11 C19 C18 -176.64(9) . . . . ? C37 N11 C19 C18 3.32(15) . . . . ? C17 C18 C19 C14 0.33(13) . . . . ? C17 C18 C19 N11 177.35(9) . . . . ? C36 N31 C32 C33 0.43(16) . . . . ? N31 C32 C33 C34 -0.70(17) . . . . ? C32 C33 C34 C35 0.39(15) . . . . ? C32 C33 C34 C37 177.99(10) . . . . ? C33 C34 C35 C36 0.13(15) . . . . ? C37 C34 C35 C36 -177.52(9) . . . . ? C32 N31 C36 C35 0.13(15) . . . . ? C34 C35 C36 N31 -0.41(16) . . . . ? C12 N11 C37 C34 -106.58(11) . . . . ? C19 N11 C37 C34 73.46(11) . . . . ? C33 C34 C37 N11 43.11(14) . . . . ? C35 C34 C37 N11 -139.37(9) . . . . ? C46 C41 C42 C43 0.94(15) . . . . ? C47 C41 C42 C43 -178.08(9) . . . . ? C41 C42 C43 C44 1.00(17) . . . . ? C42 C43 C44 F44 177.54(10) . . . . ? C42 C43 C44 C45 -2.65(18) . . . . ? F44 C44 C45 C46 -177.96(9) . . . . ? C43 C44 C45 C46 2.24(17) . . . . ? C44 C45 C46 C41 -0.18(15) . . . . ? C42 C41 C46 C45 -1.36(14) . . . . ? C47 C41 C46 C45 177.66(9) . . . . ? C46 C41 C47 N47 -166.74(9) . . . . ? C42 C41 C47 N47 12.27(14) . . . . ? C46 C41 C47 C48 12.36(13) . . . . ? C42 C41 C47 C48 -168.63(9) . . . . ? C48 C47 N47 O47 1.06(12) . . . . ? C41 C47 N47 O47 -179.84(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O47 H47 N13 1.047(10) 1.596(10) 2.6407(10) 175.9(8) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.136 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 #END