# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Christer Aakeroy' _publ_contact_author_address ;Department of Chemistry Kansas State University Manhattan, KS, 66506, USA ; _publ_contact_author_email aakeroy@ksu.edu _publ_contact_author_phone '1 785 532 6096' _publ_section_title ; Constructing, deconstructing, and reconstructing ternary supermolecules ; loop_ _publ_author_name 'C.B. Aakeroy' 'John Desper' 'Michelle M. Smith' # Attachment 'all.cif' data_15 _database_code_depnum_ccdc_archive 'CCDC 647757' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 621 4-carboxy-PhC(CN)=NOH, 1-[(4-pyridyl)methyl]-5,6-Me2-benzimidazole ; _chemical_name_common ;621 4-carboxy-PhC(CN)=NOH, 1-((4-pyridyl)methyl)-5,6-Me2- benzimidazole ; _chemical_melting_point ? _chemical_formula_moiety ; (C9 H6 N2 O3) (C15 H15 N3) ; _chemical_formula_sum 'C24 H21 N5 O3' _chemical_formula_weight 427.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 11.0553(13) _cell_length_b 7.3121(9) _cell_length_c 13.2662(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.693(7) _cell_angle_gamma 90.00 _cell_volume 1068.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3427 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 28.05 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.091 _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 12367 _diffrn_reflns_av_R_equivalents 0.1420 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.25 _reflns_number_total 2511 _reflns_number_gt 2287 _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 2511 _refine_ls_number_parameters 297 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1298 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.029 _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 N11 N 0.6008(2) 0.7654(3) 0.15322(18) 0.0393(5) Uani 1 1 d . . . C12 C 0.5717(3) 0.7937(4) 0.0533(2) 0.0437(6) Uani 1 1 d . . . H12 H 0.4945 0.8361 0.0265 0.052 Uiso 1 1 calc R . . N13 N 0.6615(2) 0.7562(3) -0.00285(18) 0.0416(5) Uani 1 1 d . . . C14 C 0.7565(2) 0.7014(3) 0.06529(18) 0.0347(5) Uani 1 1 d . . . C15 C 0.8742(2) 0.6511(3) 0.0479(2) 0.0360(5) Uani 1 1 d . . . H15 H 0.8991 0.6484 -0.0189 0.043 Uiso 1 1 calc R . . C16 C 0.9536(2) 0.6054(3) 0.1287(2) 0.0356(5) Uani 1 1 d . . . C17 C 0.9161(2) 0.6094(3) 0.2290(2) 0.0375(5) Uani 1 1 d . . . C18 C 0.7989(2) 0.6587(3) 0.2463(2) 0.0366(5) Uani 1 1 d . . . H18 H 0.7731 0.6608 0.3128 0.044 Uiso 1 1 calc R . . C19 C 0.7201(2) 0.7049(3) 0.16358(19) 0.0331(5) Uani 1 1 d . . . C20 C 1.0813(3) 0.5504(4) 0.1107(2) 0.0431(6) Uani 1 1 d . . . H20A H 1.0936 0.5640 0.0388 0.065 Uiso 1 1 calc R . . H20B H 1.0946 0.4225 0.1309 0.065 Uiso 1 1 calc R . . H20C H 1.1389 0.6287 0.1508 0.065 Uiso 1 1 calc R . . C21 C 1.0055(3) 0.5607(4) 0.3163(2) 0.0490(6) Uani 1 1 d . . . H21A H 0.9683 0.5808 0.3800 0.073 Uiso 1 1 calc R . . H21B H 1.0778 0.6377 0.3147 0.073 Uiso 1 1 calc R . . H21C H 1.0285 0.4318 0.3112 0.073 Uiso 1 1 calc R . . C22 C 0.5211(3) 0.7988(4) 0.2331(2) 0.0433(6) Uani 1 1 d . . . H22A H 0.4606 0.8924 0.2096 0.052 Uiso 1 1 calc R . . H22B H 0.5699 0.8494 0.2926 0.052 Uiso 1 1 calc R . . N31 N 0.3326(2) 0.3266(4) 0.3304(2) 0.0499(6) Uani 1 1 d . . . C32 C 0.3727(3) 0.3321(4) 0.2392(2) 0.0468(6) Uani 1 1 d . . . H32 H 0.3590 0.2293 0.1960 0.056 Uiso 1 1 calc R . . C33 C 0.4338(3) 0.4811(4) 0.2041(2) 0.0424(6) Uani 1 1 d . . . H33 H 0.4609 0.4798 0.1380 0.051 Uiso 1 1 calc R . . C34 C 0.4551(2) 0.6316(4) 0.26560(19) 0.0369(5) Uani 1 1 d . . . C35 C 0.4115(3) 0.6278(5) 0.3610(2) 0.0532(8) Uani 1 1 d . . . H35 H 0.4225 0.7292 0.4056 0.064 Uiso 1 1 calc R . . C36 C 0.3518(3) 0.4723(6) 0.3888(2) 0.0631(10) Uani 1 1 d . . . H36 H 0.3226 0.4696 0.4542 0.076 Uiso 1 1 calc R . . C41 C 0.0987(2) -0.0185(3) 0.54644(18) 0.0313(5) Uani 1 1 d . . . C47 C 0.2074(2) 0.0572(4) 0.5022(2) 0.0374(5) Uani 1 1 d . . . O41 O 0.1898(2) 0.0845(4) 0.40372(15) 0.0521(6) Uani 1 1 d . . . H41 H 0.249(5) 0.149(6) 0.386(3) 0.063 Uiso 1 1 d . . . O42 O 0.29939(19) 0.0935(4) 0.55182(17) 0.0583(6) Uani 1 1 d . . . C42 C 0.0982(2) -0.0298(3) 0.65104(17) 0.0324(5) Uani 1 1 d . . . H42 H 0.1695 0.0007 0.6925 0.039 Uiso 1 1 calc R . . C43 C -0.0046(2) -0.0850(3) 0.69538(16) 0.0311(5) Uani 1 1 d . . . H43 H -0.0039 -0.0933 0.7669 0.037 Uiso 1 1 calc R . . C44 C -0.1094(2) -0.1284(3) 0.63430(18) 0.0300(4) Uani 1 1 d . . . C45 C -0.1077(2) -0.1217(4) 0.52966(17) 0.0360(5) Uani 1 1 d . . . H45 H -0.1779 -0.1556 0.4878 0.043 Uiso 1 1 calc R . . C46 C -0.0047(2) -0.0663(4) 0.48641(17) 0.0366(5) Uani 1 1 d . . . H46 H -0.0046 -0.0610 0.4149 0.044 Uiso 1 1 calc R . . C48 C -0.2219(2) -0.1767(3) 0.67940(18) 0.0334(5) Uani 1 1 d . . . N48 N -0.2283(2) -0.1798(3) 0.77606(16) 0.0366(5) Uani 1 1 d . . . O48 O -0.34153(19) -0.2234(3) 0.80109(16) 0.0470(5) Uani 1 1 d . . . H48 H -0.340(4) -0.240(5) 0.875(3) 0.056 Uiso 1 1 d . . . C49 C -0.3270(3) -0.2153(4) 0.6118(2) 0.0449(6) Uani 1 1 d . . . N49 N -0.4092(3) -0.2418(6) 0.5562(3) 0.0700(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0301(11) 0.0412(11) 0.0492(11) 0.0056(9) 0.0181(9) -0.0006(8) C12 0.0316(13) 0.0467(14) 0.0546(15) 0.0091(12) 0.0151(11) 0.0003(11) N13 0.0308(11) 0.0504(12) 0.0444(11) 0.0068(10) 0.0091(9) -0.0010(9) C14 0.0319(13) 0.0331(12) 0.0405(11) 0.0015(9) 0.0111(9) -0.0043(9) C15 0.0322(12) 0.0343(11) 0.0433(11) 0.0016(9) 0.0144(10) -0.0017(9) C16 0.0295(12) 0.0281(11) 0.0503(13) -0.0030(10) 0.0100(10) -0.0032(9) C17 0.0377(13) 0.0281(11) 0.0468(13) -0.0014(9) 0.0049(10) -0.0011(9) C18 0.0390(14) 0.0320(11) 0.0403(12) -0.0001(9) 0.0113(10) -0.0038(10) C19 0.0287(11) 0.0297(11) 0.0429(12) 0.0013(9) 0.0148(9) -0.0018(9) C20 0.0307(13) 0.0373(12) 0.0626(15) 0.0003(12) 0.0118(11) 0.0027(10) C21 0.0504(16) 0.0454(14) 0.0504(14) 0.0010(12) -0.0002(12) 0.0016(13) C22 0.0358(14) 0.0445(14) 0.0529(14) 0.0001(12) 0.0233(12) 0.0017(11) N31 0.0399(13) 0.0591(15) 0.0518(13) 0.0171(12) 0.0101(10) -0.0090(11) C32 0.0380(14) 0.0465(15) 0.0579(15) 0.0063(12) 0.0162(12) -0.0003(11) C33 0.0397(13) 0.0445(14) 0.0457(13) 0.0061(11) 0.0201(11) 0.0046(11) C34 0.0216(11) 0.0491(14) 0.0414(12) 0.0074(10) 0.0115(9) 0.0033(9) C35 0.0519(18) 0.073(2) 0.0353(12) -0.0020(12) 0.0104(12) -0.0154(15) C36 0.058(2) 0.096(3) 0.0372(13) 0.0105(16) 0.0128(13) -0.0248(19) C41 0.0304(11) 0.0292(10) 0.0354(10) 0.0021(8) 0.0082(8) 0.0002(8) C47 0.0311(12) 0.0394(12) 0.0432(12) 0.0035(10) 0.0113(9) -0.0022(10) O41 0.0460(12) 0.0713(14) 0.0402(9) 0.0121(9) 0.0105(8) -0.0203(10) O42 0.0294(10) 0.0937(18) 0.0521(11) 0.0131(11) 0.0052(9) -0.0095(10) C42 0.0305(11) 0.0340(11) 0.0325(10) 0.0020(9) 0.0018(8) 0.0011(9) C43 0.0320(12) 0.0337(11) 0.0281(9) -0.0002(9) 0.0059(8) 0.0014(9) C44 0.0316(11) 0.0265(10) 0.0331(10) 0.0017(8) 0.0093(8) -0.0003(8) C45 0.0359(13) 0.0400(12) 0.0318(11) 0.0000(9) 0.0017(9) -0.0090(10) C46 0.0419(14) 0.0407(13) 0.0279(9) 0.0019(9) 0.0060(9) -0.0066(10) C48 0.0310(12) 0.0322(11) 0.0378(11) 0.0044(9) 0.0073(9) -0.0018(9) N48 0.0310(11) 0.0391(11) 0.0408(10) 0.0054(8) 0.0093(8) 0.0005(8) O48 0.0314(10) 0.0664(14) 0.0445(10) 0.0109(9) 0.0110(8) -0.0029(9) C49 0.0362(14) 0.0550(16) 0.0440(13) 0.0086(12) 0.0056(11) -0.0115(12) N49 0.0463(16) 0.101(3) 0.0606(16) 0.0244(16) -0.0087(13) -0.0274(16) _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 1.354(4) . ? N11 C19 1.387(3) . ? N11 C22 1.453(3) . ? C12 N13 1.317(4) . ? C12 H12 0.9500 . ? N13 C14 1.388(4) . ? C14 C15 1.389(3) . ? C14 C19 1.396(3) . ? C15 C16 1.370(4) . ? C15 H15 0.9500 . ? C16 C17 1.426(4) . ? C16 C20 1.506(4) . ? C17 C18 1.382(4) . ? C17 C21 1.502(4) . ? C18 C19 1.386(4) . ? 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 . ? C22 C34 1.504(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? N31 C32 1.323(4) . ? N31 C36 1.324(5) . ? C32 C33 1.382(4) . ? C32 H32 0.9500 . ? C33 C34 1.379(4) . ? C33 H33 0.9500 . ? C34 C35 1.391(3) . ? C35 C36 1.381(5) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.383(4) . ? C41 C42 1.390(3) . ? C41 C47 1.487(3) . ? C47 O42 1.195(3) . ? C47 O41 1.320(3) . ? O41 H41 0.86(5) . ? C42 C43 1.382(3) . ? C42 H42 0.9500 . ? C43 C44 1.396(3) . ? C43 H43 0.9500 . ? C44 C45 1.391(3) . ? C44 C48 1.467(3) . ? C45 C46 1.377(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C48 N48 1.290(3) . ? C48 C49 1.436(4) . ? N48 O48 1.359(3) . ? O48 H48 0.98(4) . ? C49 N49 1.139(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C19 107.0(2) . . ? C12 N11 C22 125.4(2) . . ? C19 N11 C22 127.6(2) . . ? N13 C12 N11 113.1(3) . . ? N13 C12 H12 123.4 . . ? N11 C12 H12 123.4 . . ? C12 N13 C14 104.9(2) . . ? N13 C14 C15 129.6(2) . . ? N13 C14 C19 110.1(2) . . ? C15 C14 C19 120.3(2) . . ? C16 C15 C14 119.0(2) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 120.5(2) . . ? C15 C16 C20 119.4(2) . . ? C17 C16 C20 120.1(2) . . ? C18 C17 C16 120.5(2) . . ? C18 C17 C21 120.0(3) . . ? C16 C17 C21 119.5(2) . . ? C17 C18 C19 118.0(2) . . ? C17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? C18 C19 N11 133.4(2) . . ? C18 C19 C14 121.7(2) . . ? N11 C19 C14 104.9(2) . . ? 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 . . ? N11 C22 C34 114.2(2) . . ? N11 C22 H22A 108.7 . . ? C34 C22 H22A 108.7 . . ? N11 C22 H22B 108.7 . . ? C34 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C32 N31 C36 117.4(3) . . ? N31 C32 C33 122.8(3) . . ? N31 C32 H32 118.6 . . ? C33 C32 H32 118.6 . . ? C34 C33 C32 119.6(2) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 117.8(3) . . ? C33 C34 C22 122.9(2) . . ? C35 C34 C22 119.3(3) . . ? C36 C35 C34 118.0(3) . . ? C36 C35 H35 121.0 . . ? C34 C35 H35 121.0 . . ? N31 C36 C35 124.3(3) . . ? N31 C36 H36 117.8 . . ? C35 C36 H36 117.8 . . ? C46 C41 C42 119.3(2) . . ? C46 C41 C47 121.5(2) . . ? C42 C41 C47 119.0(2) . . ? O42 C47 O41 124.2(2) . . ? O42 C47 C41 123.0(2) . . ? O41 C47 C41 112.8(2) . . ? C47 O41 H41 107(3) . . ? C43 C42 C41 120.8(2) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C44 119.5(2) . . ? C42 C43 H43 120.3 . . ? C44 C43 H43 120.3 . . ? C45 C44 C43 119.5(2) . . ? C45 C44 C48 119.8(2) . . ? C43 C44 C48 120.6(2) . . ? C46 C45 C44 120.4(2) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C41 120.5(2) . . ? C45 C46 H46 119.8 . . ? C41 C46 H46 119.8 . . ? N48 C48 C49 120.7(2) . . ? N48 C48 C44 121.8(2) . . ? C49 C48 C44 117.5(2) . . ? C48 N48 O48 111.9(2) . . ? N48 O48 H48 109(3) . . ? N49 C49 C48 177.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C19 N11 C12 N13 0.3(3) . . . . ? C22 N11 C12 N13 178.6(3) . . . . ? N11 C12 N13 C14 -0.7(3) . . . . ? C12 N13 C14 C15 -178.0(3) . . . . ? C12 N13 C14 C19 0.8(3) . . . . ? N13 C14 C15 C16 178.6(3) . . . . ? C19 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C17 0.0(3) . . . . ? C14 C15 C16 C20 179.9(2) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C20 C16 C17 C18 -179.6(2) . . . . ? C15 C16 C17 C21 -179.3(2) . . . . ? C20 C16 C17 C21 0.8(4) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C21 C17 C18 C19 179.1(2) . . . . ? C17 C18 C19 N11 -177.4(3) . . . . ? C17 C18 C19 C14 0.4(3) . . . . ? C12 N11 C19 C18 178.3(3) . . . . ? C22 N11 C19 C18 0.0(4) . . . . ? C12 N11 C19 C14 0.2(3) . . . . ? C22 N11 C19 C14 -178.0(2) . . . . ? N13 C14 C19 C18 -179.0(2) . . . . ? C15 C14 C19 C18 -0.1(4) . . . . ? N13 C14 C19 N11 -0.7(3) . . . . ? C15 C14 C19 N11 178.3(2) . . . . ? C12 N11 C22 C34 96.6(3) . . . . ? C19 N11 C22 C34 -85.4(3) . . . . ? C36 N31 C32 C33 0.7(5) . . . . ? N31 C32 C33 C34 0.2(5) . . . . ? C32 C33 C34 C35 -1.2(4) . . . . ? C32 C33 C34 C22 179.9(3) . . . . ? N11 C22 C34 C33 -23.4(4) . . . . ? N11 C22 C34 C35 157.6(3) . . . . ? C33 C34 C35 C36 1.3(5) . . . . ? C22 C34 C35 C36 -179.7(3) . . . . ? C32 N31 C36 C35 -0.6(6) . . . . ? C34 C35 C36 N31 -0.4(6) . . . . ? C46 C41 C47 O42 -177.2(3) . . . . ? C42 C41 C47 O42 7.1(4) . . . . ? C46 C41 C47 O41 4.7(4) . . . . ? C42 C41 C47 O41 -171.0(2) . . . . ? C46 C41 C42 C43 -1.2(4) . . . . ? C47 C41 C42 C43 174.6(2) . . . . ? C41 C42 C43 C44 -0.5(4) . . . . ? C42 C43 C44 C45 2.2(3) . . . . ? C42 C43 C44 C48 -176.3(2) . . . . ? C43 C44 C45 C46 -2.3(4) . . . . ? C48 C44 C45 C46 176.2(2) . . . . ? C44 C45 C46 C41 0.7(4) . . . . ? C42 C41 C46 C45 1.1(4) . . . . ? C47 C41 C46 C45 -174.6(2) . . . . ? C45 C44 C48 N48 -178.2(2) . . . . ? C43 C44 C48 N48 0.4(3) . . . . ? C45 C44 C48 C49 -0.1(4) . . . . ? C43 C44 C48 C49 178.5(2) . . . . ? C49 C48 N48 O48 0.4(4) . . . . ? C44 C48 N48 O48 178.4(2) . . . . ? 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 O41 H41 N31 0.86(5) 1.79(5) 2.612(3) 161(5) . O48 H48 N13 0.98(4) 1.62(4) 2.603(3) 174(4) 1_446 _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.287 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.064 #END data_478 _database_code_depnum_ccdc_archive 'CCDC 647758' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-[(4-pyridyl)methyl]-2-methylbenzimidazole, PhC(CN)(=NOH) Me5-PhCOOH ; _chemical_name_common ;1-((4-pyridyl)methyl)-2-methylbenzimidazole, PhC(CN)(=NOH) Me5-PhCOOH ; _chemical_melting_point ? _chemical_formula_moiety ; (C14 H13 N3) (C8 H6 N2 O) (C12 H16 O2) ; _chemical_formula_sum 'C34 H35 N5 O3' _chemical_formula_weight 561.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.7988(10) _cell_length_b 31.336(5) _cell_length_c 8.4715(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.377(7) _cell_angle_gamma 90.00 _cell_volume 1476.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9972 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 30.55 _exptl_crystal_description plate _exptl_crystal_colour colourless _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 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9678 _exptl_absorpt_correction_T_max 0.9934 _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 50681 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 30.50 _reflns_number_total 4599 _reflns_number_gt 4208 _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^)+(0.0700P)^2^+0.1500P] 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 4599 _refine_ls_number_parameters 391 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.104 _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 0.0171(2) 0.49869(5) 0.74172(18) 0.0205(3) Uani 1 1 d . . . C12 C 0.2165(3) 0.48690(6) 0.8634(2) 0.0205(3) Uani 1 1 d . . . N13 N 0.3940(2) 0.51461(5) 0.87959(19) 0.0216(3) Uani 1 1 d . . . C14 C 0.3077(3) 0.54607(6) 0.7624(2) 0.0207(3) Uani 1 1 d . . . C15 C 0.4204(3) 0.58230(6) 0.7233(2) 0.0272(4) Uani 1 1 d . . . H15 H 0.5822 0.5889 0.7806 0.033 Uiso 1 1 calc R . . C16 C 0.2888(4) 0.60813(7) 0.5985(3) 0.0318(4) Uani 1 1 d . . . H16 H 0.3621 0.6328 0.5690 0.038 Uiso 1 1 calc R . . C17 C 0.0493(4) 0.59880(7) 0.5142(3) 0.0332(4) Uani 1 1 d . . . H17 H -0.0368 0.6175 0.4299 0.040 Uiso 1 1 calc R . . C18 C -0.0646(3) 0.56288(7) 0.5510(2) 0.0287(4) Uani 1 1 d . . . H18 H -0.2268 0.5564 0.4940 0.034 Uiso 1 1 calc R . . C19 C 0.0700(3) 0.53672(6) 0.6756(2) 0.0207(3) Uani 1 1 d . . . C20 C 0.2305(4) 0.44801(6) 0.9664(2) 0.0281(4) Uani 1 1 d . . . H20A H 0.3914 0.4355 0.9890 0.042 Uiso 1 1 calc R . . H20B H 0.1106 0.4272 0.9077 0.042 Uiso 1 1 calc R . . H20C H 0.1986 0.4557 1.0705 0.042 Uiso 1 1 calc R . . N21 N -0.3217(3) 0.38887(6) 0.2870(2) 0.0312(4) Uani 1 1 d . . . C22 C -0.4312(4) 0.38445(8) 0.4035(3) 0.0380(5) Uani 1 1 d . . . H22 H -0.5391 0.3612 0.3964 0.046 Uiso 1 1 calc R . . C23 C -0.3956(4) 0.41207(7) 0.5348(3) 0.0315(4) Uani 1 1 d . . . H23 H -0.4798 0.4081 0.6150 0.038 Uiso 1 1 calc R . . C24 C -0.2359(3) 0.44569(5) 0.5489(2) 0.0195(3) Uani 1 1 d . . . C25 C -0.1185(4) 0.45035(7) 0.4290(2) 0.0283(4) Uani 1 1 d . . . H25 H -0.0058 0.4727 0.4349 0.034 Uiso 1 1 calc R . . C26 C -0.1700(4) 0.42137(7) 0.2992(3) 0.0324(4) Uani 1 1 d . . . H26 H -0.0929 0.4250 0.2150 0.039 Uiso 1 1 calc R . . C27 C -0.2114(3) 0.47635(6) 0.6902(2) 0.0224(3) Uani 1 1 d . . . H27A H -0.3419 0.4977 0.6580 0.027 Uiso 1 1 calc R . . H27B H -0.2339 0.4603 0.7854 0.027 Uiso 1 1 calc R . . C31 C 1.2290(3) 0.60652(6) 1.0902(2) 0.0235(3) Uani 1 1 d . . . C32 C 1.1044(4) 0.63432(7) 0.9684(3) 0.0332(4) Uani 1 1 d . . . H32 H 0.9446 0.6277 0.9065 0.040 Uiso 1 1 calc R . . C33 C 1.2102(4) 0.67156(7) 0.9363(3) 0.0371(5) Uani 1 1 d . . . H33 H 1.1232 0.6901 0.8517 0.044 Uiso 1 1 calc R . . C34 C 1.4395(5) 0.68205(8) 1.0254(3) 0.0423(5) Uani 1 1 d . . . H34 H 1.5105 0.7081 1.0056 0.051 Uiso 1 1 calc R . . C35 C 1.5644(5) 0.65426(11) 1.1436(4) 0.0634(10) Uani 1 1 d . . . H35 H 1.7247 0.6609 1.2042 0.076 Uiso 1 1 calc R . . C36 C 1.4617(4) 0.61659(9) 1.1764(4) 0.0492(7) Uani 1 1 d . . . H36 H 1.5518 0.5977 1.2585 0.059 Uiso 1 1 calc R . . C37 C 1.1199(3) 0.56618(6) 1.1241(2) 0.0215(3) Uani 1 1 d . . . N37 N 0.9039(3) 0.55619(5) 1.0411(2) 0.0241(3) Uani 1 1 d . . . O37 O 0.8293(2) 0.51782(5) 1.08706(18) 0.0279(3) Uani 1 1 d . . . H37 H 0.677(5) 0.5174(9) 1.011(3) 0.034 Uiso 1 1 d . . . C38 C 1.2570(3) 0.53758(6) 1.2512(2) 0.0246(3) Uani 1 1 d . . . N38 N 1.3632(3) 0.51497(7) 1.3506(2) 0.0346(4) Uani 1 1 d . . . C41 C -0.4326(3) 0.31211(6) -0.2174(2) 0.0235(3) Uani 1 1 d . . . C42 C -0.2665(3) 0.28024(6) -0.2211(2) 0.0241(3) Uani 1 1 d . . . C43 C -0.3167(4) 0.25174(6) -0.3544(2) 0.0264(4) Uani 1 1 d . . . C44 C -0.5302(4) 0.25623(6) -0.4823(2) 0.0288(4) Uani 1 1 d . . . C45 C -0.6968(3) 0.28782(6) -0.4749(2) 0.0250(3) Uani 1 1 d . . . C46 C -0.6495(3) 0.31600(6) -0.3407(2) 0.0229(3) Uani 1 1 d . . . C51 C -0.3730(3) 0.34453(7) -0.0791(2) 0.0277(4) Uani 1 1 d . . . O51 O -0.4284(3) 0.33135(6) 0.05275(19) 0.0381(4) Uani 1 1 d . . . H51 H -0.386(5) 0.3528(11) 0.148(4) 0.046 Uiso 1 1 d . . . O52 O -0.2830(4) 0.37873(6) -0.0891(2) 0.0421(4) Uani 1 1 d . . . C52 C -0.0353(4) 0.27694(8) -0.0845(3) 0.0327(4) Uani 1 1 d . . . H52A H 0.1007 0.2759 -0.1317 0.049 Uiso 1 1 calc R . . H52B H -0.0374 0.2509 -0.0209 0.049 Uiso 1 1 calc R . . H52C H -0.0190 0.3018 -0.0122 0.049 Uiso 1 1 calc R . . C53 C -0.1402(5) 0.21642(8) -0.3557(3) 0.0402(5) Uani 1 1 d . . . H53A H -0.1402 0.2105 -0.4693 0.060 Uiso 1 1 calc R . . H53B H -0.1869 0.1906 -0.3071 0.060 Uiso 1 1 calc R . . H53C H 0.0212 0.2252 -0.2916 0.060 Uiso 1 1 calc R . . C54 C -0.5803(5) 0.22705(10) -0.6310(3) 0.0519(7) Uani 1 1 d . . . H54A H -0.4284 0.2157 -0.6424 0.078 Uiso 1 1 calc R . . H54B H -0.6618 0.2432 -0.7301 0.078 Uiso 1 1 calc R . . H54C H -0.6832 0.2034 -0.6167 0.078 Uiso 1 1 calc R . . C55 C -0.9291(4) 0.29272(8) -0.6107(3) 0.0365(5) Uani 1 1 d . . . H55A H -1.0495 0.3066 -0.5669 0.055 Uiso 1 1 calc R . . H55B H -0.9876 0.2645 -0.6540 0.055 Uiso 1 1 calc R . . H55C H -0.9007 0.3102 -0.6993 0.055 Uiso 1 1 calc R . . C56 C -0.8287(3) 0.35010(7) -0.3305(3) 0.0299(4) Uani 1 1 d . . . H56A H -0.8531 0.3694 -0.4249 0.045 Uiso 1 1 calc R . . H56B H -0.7674 0.3663 -0.2284 0.045 Uiso 1 1 calc R . . H56C H -0.9819 0.3367 -0.3317 0.045 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 N11 0.0177(6) 0.0214(7) 0.0208(7) -0.0043(6) 0.0030(5) -0.0039(5) C12 0.0206(7) 0.0190(7) 0.0214(8) -0.0044(6) 0.0053(6) 0.0004(6) N13 0.0183(6) 0.0209(7) 0.0237(7) -0.0023(6) 0.0027(5) -0.0014(5) C14 0.0185(6) 0.0212(8) 0.0206(8) -0.0027(6) 0.0025(6) -0.0007(6) C15 0.0249(8) 0.0236(9) 0.0292(9) -0.0001(7) 0.0014(7) -0.0067(6) C16 0.0342(9) 0.0229(9) 0.0343(10) 0.0035(8) 0.0033(8) -0.0059(7) C17 0.0343(9) 0.0281(10) 0.0300(10) 0.0060(8) -0.0025(8) 0.0000(8) C18 0.0242(8) 0.0292(9) 0.0270(9) 0.0015(8) -0.0018(6) 0.0006(7) C19 0.0193(7) 0.0212(8) 0.0203(8) -0.0046(6) 0.0030(6) -0.0016(6) C20 0.0331(8) 0.0230(9) 0.0273(9) 0.0009(7) 0.0069(7) -0.0011(7) N21 0.0396(9) 0.0280(8) 0.0218(8) -0.0039(6) 0.0017(6) -0.0022(7) C22 0.0473(12) 0.0344(11) 0.0299(11) -0.0082(9) 0.0073(9) -0.0184(10) C23 0.0369(9) 0.0312(10) 0.0278(9) -0.0050(8) 0.0114(8) -0.0134(8) C24 0.0210(6) 0.0180(7) 0.0166(7) -0.0009(6) 0.0007(5) -0.0012(6) C25 0.0353(9) 0.0253(9) 0.0266(9) -0.0029(7) 0.0125(7) -0.0058(7) C26 0.0433(11) 0.0331(11) 0.0232(9) -0.0019(8) 0.0133(8) -0.0018(8) C27 0.0191(6) 0.0266(9) 0.0214(8) -0.0064(7) 0.0055(6) -0.0063(6) C31 0.0221(7) 0.0249(9) 0.0227(8) -0.0022(7) 0.0052(6) 0.0000(6) C32 0.0349(10) 0.0271(10) 0.0305(10) 0.0022(8) -0.0024(8) -0.0014(8) C33 0.0441(11) 0.0280(10) 0.0342(11) 0.0047(9) 0.0032(9) -0.0010(9) C34 0.0430(12) 0.0353(12) 0.0473(14) 0.0095(10) 0.0105(10) -0.0107(9) C35 0.0369(12) 0.0605(18) 0.076(2) 0.0283(16) -0.0115(12) -0.0248(12) C36 0.0283(10) 0.0481(14) 0.0578(16) 0.0242(12) -0.0099(10) -0.0149(9) C37 0.0196(7) 0.0225(8) 0.0207(8) 0.0000(6) 0.0028(6) 0.0007(6) N37 0.0211(6) 0.0235(8) 0.0256(7) -0.0001(6) 0.0030(5) -0.0004(5) O37 0.0210(5) 0.0265(7) 0.0310(7) 0.0044(6) -0.0013(5) -0.0046(5) C38 0.0192(7) 0.0265(9) 0.0253(9) -0.0005(7) 0.0016(6) -0.0020(6) N38 0.0267(7) 0.0340(9) 0.0369(9) 0.0054(8) -0.0013(7) -0.0009(7) C41 0.0260(7) 0.0238(8) 0.0187(8) -0.0028(6) 0.0029(6) -0.0018(6) C42 0.0267(8) 0.0239(8) 0.0189(8) 0.0017(7) 0.0016(6) 0.0003(6) C43 0.0313(9) 0.0215(9) 0.0244(9) -0.0018(7) 0.0044(7) 0.0031(7) C44 0.0387(10) 0.0220(9) 0.0214(9) -0.0060(7) 0.0015(7) -0.0008(7) C45 0.0283(8) 0.0233(9) 0.0187(8) -0.0012(7) -0.0009(6) -0.0012(6) C46 0.0254(7) 0.0210(8) 0.0202(8) -0.0016(6) 0.0028(6) -0.0012(6) C51 0.0285(8) 0.0302(10) 0.0217(8) -0.0050(7) 0.0025(6) 0.0003(7) O51 0.0547(10) 0.0362(8) 0.0242(7) -0.0084(6) 0.0122(7) -0.0115(7) O52 0.0584(10) 0.0333(8) 0.0344(8) -0.0104(7) 0.0127(7) -0.0162(8) C52 0.0298(8) 0.0363(11) 0.0259(10) 0.0036(8) -0.0020(7) 0.0027(8) C53 0.0443(11) 0.0299(11) 0.0430(13) -0.0038(9) 0.0069(9) 0.0119(9) C54 0.0583(15) 0.0460(15) 0.0400(13) -0.0264(12) -0.0046(11) 0.0111(12) C55 0.0354(10) 0.0374(11) 0.0262(10) -0.0047(9) -0.0084(8) -0.0007(9) C56 0.0273(8) 0.0289(10) 0.0317(10) -0.0026(8) 0.0055(7) 0.0044(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.365(2) . ? N11 C19 1.387(2) . ? N11 C27 1.452(2) . ? C12 N13 1.324(2) . ? C12 C20 1.488(3) . ? N13 C14 1.388(2) . ? C14 C15 1.396(2) . ? C14 C19 1.398(2) . ? C15 C16 1.378(3) . ? C15 H15 0.9500 . ? C16 C17 1.402(3) . ? C16 H16 0.9500 . ? C17 C18 1.384(3) . ? C17 H17 0.9500 . ? C18 C19 1.389(3) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? N21 C22 1.323(3) . ? N21 C26 1.331(3) . ? C22 C23 1.378(3) . ? C22 H22 0.9500 . ? C23 C24 1.386(2) . ? C23 H23 0.9500 . ? C24 C25 1.381(2) . ? C24 C27 1.510(2) . ? C25 C26 1.392(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C36 1.377(3) . ? C31 C32 1.388(3) . ? C31 C37 1.478(3) . ? C32 C33 1.381(3) . ? C32 H32 0.9500 . ? C33 C34 1.371(3) . ? C33 H33 0.9500 . ? C34 C35 1.370(4) . ? C34 H34 0.9500 . ? C35 C36 1.385(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 N37 1.290(2) . ? C37 C38 1.454(3) . ? N37 O37 1.371(2) . ? O37 H37 0.94(3) . ? C38 N38 1.139(3) . ? C41 C42 1.394(3) . ? C41 C46 1.395(2) . ? C41 C51 1.515(3) . ? C42 C43 1.405(3) . ? C42 C52 1.507(3) . ? C43 C44 1.403(3) . ? C43 C53 1.510(3) . ? C44 C45 1.397(3) . ? C44 C54 1.517(3) . ? C45 C46 1.404(3) . ? C45 C55 1.513(3) . ? C46 C56 1.510(3) . ? C51 O52 1.206(3) . ? C51 O51 1.313(3) . ? O51 H51 1.03(3) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 H53A 0.9800 . ? C53 H53B 0.9800 . ? C53 H53C 0.9800 . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 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 N11 C19 107.48(14) . . ? C12 N11 C27 127.10(16) . . ? C19 N11 C27 125.42(15) . . ? N13 C12 N11 111.67(16) . . ? N13 C12 C20 124.34(16) . . ? N11 C12 C20 123.98(16) . . ? C12 N13 C14 106.17(14) . . ? N13 C14 C15 130.48(16) . . ? N13 C14 C19 109.30(15) . . ? C15 C14 C19 120.22(16) . . ? C16 C15 C14 117.72(17) . . ? C16 C15 H15 121.1 . . ? C14 C15 H15 121.1 . . ? C15 C16 C17 121.51(19) . . ? C15 C16 H16 119.2 . . ? C17 C16 H16 119.2 . . ? C18 C17 C16 121.45(18) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 116.70(17) . . ? C17 C18 H18 121.7 . . ? C19 C18 H18 121.7 . . ? N11 C19 C18 132.26(16) . . ? N11 C19 C14 105.37(15) . . ? C18 C19 C14 122.38(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 N21 C26 117.91(18) . . ? N21 C22 C23 122.8(2) . . ? N21 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C24 119.47(18) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C25 C24 C23 118.23(17) . . ? C25 C24 C27 124.07(16) . . ? C23 C24 C27 117.62(15) . . ? C24 C25 C26 118.15(18) . . ? C24 C25 H25 120.9 . . ? C26 C25 H25 120.9 . . ? N21 C26 C25 123.40(18) . . ? N21 C26 H26 118.3 . . ? C25 C26 H26 118.3 . . ? N11 C27 C24 114.77(14) . . ? N11 C27 H27A 108.6 . . ? C24 C27 H27A 108.6 . . ? N11 C27 H27B 108.6 . . ? C24 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? C36 C31 C32 118.53(19) . . ? C36 C31 C37 120.14(18) . . ? C32 C31 C37 121.31(17) . . ? C33 C32 C31 120.64(19) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 120.7(2) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C35 C34 C33 118.7(2) . . ? C35 C34 H34 120.6 . . ? C33 C34 H34 120.6 . . ? C34 C35 C36 121.3(2) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C31 C36 C35 120.1(2) . . ? C31 C36 H36 120.0 . . ? C35 C36 H36 120.0 . . ? N37 C37 C38 119.89(17) . . ? N37 C37 C31 120.33(16) . . ? C38 C37 C31 119.78(15) . . ? C37 N37 O37 113.19(15) . . ? N37 O37 H37 97.5(18) . . ? N38 C38 C37 179.5(2) . . ? C42 C41 C46 121.90(17) . . ? C42 C41 C51 119.31(16) . . ? C46 C41 C51 118.75(16) . . ? C41 C42 C43 119.05(16) . . ? C41 C42 C52 120.18(17) . . ? C43 C42 C52 120.77(18) . . ? C44 C43 C42 119.68(17) . . ? C44 C43 C53 121.32(18) . . ? C42 C43 C53 118.99(18) . . ? C45 C44 C43 120.45(17) . . ? C45 C44 C54 119.43(19) . . ? C43 C44 C54 120.1(2) . . ? C44 C45 C46 120.14(16) . . ? C44 C45 C55 121.10(18) . . ? C46 C45 C55 118.75(18) . . ? C41 C46 C45 118.71(17) . . ? C41 C46 C56 120.59(16) . . ? C45 C46 C56 120.69(16) . . ? O52 C51 O51 123.65(19) . . ? O52 C51 C41 123.41(18) . . ? O51 C51 C41 112.93(18) . . ? C51 O51 H51 113.8(18) . . ? C42 C52 H52A 109.5 . . ? C42 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C42 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C43 C53 H53A 109.5 . . ? C43 C53 H53B 109.5 . . ? H53A C53 H53B 109.5 . . ? C43 C53 H53C 109.5 . . ? H53A C53 H53C 109.5 . . ? H53B C53 H53C 109.5 . . ? C44 C54 H54A 109.5 . . ? C44 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C44 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? C45 C55 H55A 109.5 . . ? C45 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? C45 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C46 C56 H56A 109.5 . . ? C46 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C46 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 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 C19 N11 C12 N13 -0.22(19) . . . . ? C27 N11 C12 N13 -179.53(15) . . . . ? C19 N11 C12 C20 178.91(16) . . . . ? C27 N11 C12 C20 -0.4(3) . . . . ? N11 C12 N13 C14 -0.28(19) . . . . ? C20 C12 N13 C14 -179.42(16) . . . . ? C12 N13 C14 C15 -178.53(19) . . . . ? C12 N13 C14 C19 0.68(19) . . . . ? N13 C14 C15 C16 179.65(19) . . . . ? C19 C14 C15 C16 0.5(3) . . . . ? C14 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C18 -0.9(4) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C12 N11 C19 C18 -179.6(2) . . . . ? C27 N11 C19 C18 -0.2(3) . . . . ? C12 N11 C19 C14 0.62(18) . . . . ? C27 N11 C19 C14 179.95(15) . . . . ? C17 C18 C19 N11 -178.79(19) . . . . ? C17 C18 C19 C14 1.0(3) . . . . ? N13 C14 C19 N11 -0.81(19) . . . . ? C15 C14 C19 N11 178.50(16) . . . . ? N13 C14 C19 C18 179.35(17) . . . . ? C15 C14 C19 C18 -1.3(3) . . . . ? C26 N21 C22 C23 0.4(4) . . . . ? N21 C22 C23 C24 -1.1(4) . . . . ? C22 C23 C24 C25 0.4(3) . . . . ? C22 C23 C24 C27 177.1(2) . . . . ? C23 C24 C25 C26 0.9(3) . . . . ? C27 C24 C25 C26 -175.61(19) . . . . ? C22 N21 C26 C25 1.0(3) . . . . ? C24 C25 C26 N21 -1.7(3) . . . . ? C12 N11 C27 C24 -93.5(2) . . . . ? C19 N11 C27 C24 87.3(2) . . . . ? C25 C24 C27 N11 -28.4(3) . . . . ? C23 C24 C27 N11 154.99(17) . . . . ? C36 C31 C32 C33 -1.0(3) . . . . ? C37 C31 C32 C33 -178.9(2) . . . . ? C31 C32 C33 C34 -0.8(4) . . . . ? C32 C33 C34 C35 1.9(4) . . . . ? C33 C34 C35 C36 -1.4(6) . . . . ? C32 C31 C36 C35 1.5(4) . . . . ? C37 C31 C36 C35 179.5(3) . . . . ? C34 C35 C36 C31 -0.3(6) . . . . ? C36 C31 C37 N37 -178.5(2) . . . . ? C32 C31 C37 N37 -0.6(3) . . . . ? C36 C31 C37 C38 1.4(3) . . . . ? C32 C31 C37 C38 179.23(19) . . . . ? C38 C37 N37 O37 0.0(2) . . . . ? C31 C37 N37 O37 179.87(15) . . . . ? C46 C41 C42 C43 1.3(3) . . . . ? C51 C41 C42 C43 -176.45(18) . . . . ? C46 C41 C42 C52 -179.45(18) . . . . ? C51 C41 C42 C52 2.8(3) . . . . ? C41 C42 C43 C44 1.1(3) . . . . ? C52 C42 C43 C44 -178.2(2) . . . . ? C41 C42 C43 C53 -178.2(2) . . . . ? C52 C42 C43 C53 2.6(3) . . . . ? C42 C43 C44 C45 -2.4(3) . . . . ? C53 C43 C44 C45 176.8(2) . . . . ? C42 C43 C44 C54 176.9(2) . . . . ? C53 C43 C44 C54 -3.9(3) . . . . ? C43 C44 C45 C46 1.4(3) . . . . ? C54 C44 C45 C46 -177.9(2) . . . . ? C43 C44 C45 C55 -179.2(2) . . . . ? C54 C44 C45 C55 1.5(3) . . . . ? C42 C41 C46 C45 -2.2(3) . . . . ? C51 C41 C46 C45 175.47(17) . . . . ? C42 C41 C46 C56 178.25(18) . . . . ? C51 C41 C46 C56 -4.0(3) . . . . ? C44 C45 C46 C41 0.9(3) . . . . ? C55 C45 C46 C41 -178.48(19) . . . . ? C44 C45 C46 C56 -179.59(18) . . . . ? C55 C45 C46 C56 1.0(3) . . . . ? C42 C41 C51 O52 93.9(3) . . . . ? C46 C41 C51 O52 -83.9(3) . . . . ? C42 C41 C51 O51 -85.7(2) . . . . ? C46 C41 C51 O51 96.5(2) . . . . ? 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(3) 1.70(3) 2.6396(19) 177(3) . O51 H51 N21 1.03(3) 1.60(3) 2.622(2) 176(3) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.403 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.044 #END #END data_26 _database_code_depnum_ccdc_archive 'CCDC 652592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-[(4-pyridyl)methyl]-2-phenylimidazole, 4-hydroxybenzoic acid ; _chemical_name_common '1-((4-pyridyl)methyl)-2-phenylimidazole, 4-hydroxybenzoic acid' _chemical_melting_point ? _chemical_formula_moiety ; (C15 H13 N3) (C7 H6 O3) ; _chemical_formula_sum 'C22 H19 N3 O3' _chemical_formula_weight 373.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0137(8) _cell_length_b 9.8024(9) _cell_length_c 12.0784(13) _cell_angle_alpha 82.364(6) _cell_angle_beta 86.045(7) _cell_angle_gamma 75.888(6) _cell_volume 911.35(16) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2490 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 27.35 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.092 _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 6742 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0876 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3987 _reflns_number_gt 2605 _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 SHELXL _refine_ls_extinction_coef 0.051(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3987 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1993 _refine_ls_wR_factor_gt 0.1795 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 N11 N 0.2858(3) 0.4120(2) 0.79592(16) 0.0288(5) Uani 1 1 d . . . C12 C 0.2825(3) 0.4060(2) 0.9096(2) 0.0280(5) Uani 1 1 d . . . N13 N 0.3037(3) 0.2731(2) 0.95539(18) 0.0346(5) Uani 1 1 d . . . C14 C 0.3223(3) 0.1925(3) 0.8693(2) 0.0387(7) Uani 1 1 d . . . H14 H 0.3400 0.0923 0.8777 0.046 Uiso 1 1 calc R . . C15 C 0.3117(3) 0.2762(3) 0.7709(2) 0.0362(6) Uani 1 1 d . . . H15 H 0.3205 0.2467 0.6984 0.043 Uiso 1 1 calc R . . N21 N 0.7011(3) 0.6576(2) 0.55633(18) 0.0347(5) Uani 1 1 d . . . C22 C 0.7072(3) 0.5234(3) 0.5962(2) 0.0368(6) Uani 1 1 d . . . H22 H 0.8126 0.4549 0.5879 0.044 Uiso 1 1 calc R . . C23 C 0.5682(3) 0.4783(3) 0.6490(2) 0.0347(6) Uani 1 1 d . . . H23 H 0.5789 0.3814 0.6770 0.042 Uiso 1 1 calc R . . C24 C 0.4137(3) 0.5760(2) 0.66052(19) 0.0277(5) Uani 1 1 d . . . C25 C 0.4077(3) 0.7153(3) 0.6193(2) 0.0327(6) Uani 1 1 d . . . H25 H 0.3042 0.7860 0.6267 0.039 Uiso 1 1 calc R . . C26 C 0.5515(3) 0.7514(3) 0.5676(2) 0.0350(6) Uani 1 1 d . . . H26 H 0.5440 0.8476 0.5386 0.042 Uiso 1 1 calc R . . C27 C 0.2527(3) 0.5365(3) 0.7130(2) 0.0314(6) Uani 1 1 d . . . H27A H 0.1821 0.6177 0.7489 0.038 Uiso 1 1 calc R . . H27B H 0.1847 0.5190 0.6533 0.038 Uiso 1 1 calc R . . C31 C 0.2562(3) 0.5271(2) 0.9729(2) 0.0271(5) Uani 1 1 d . . . C32 C 0.3238(3) 0.6445(3) 0.9364(2) 0.0300(6) Uani 1 1 d . . . H32 H 0.3912 0.6471 0.8687 0.036 Uiso 1 1 calc R . . C33 C 0.2927(3) 0.7566(3) 0.9986(2) 0.0349(6) Uani 1 1 d . . . H33 H 0.3372 0.8371 0.9727 0.042 Uiso 1 1 calc R . . C34 C 0.1977(3) 0.7536(3) 1.0983(2) 0.0401(7) Uani 1 1 d . . . H34 H 0.1767 0.8313 1.1408 0.048 Uiso 1 1 calc R . . C35 C 0.1334(3) 0.6365(3) 1.1356(2) 0.0394(7) Uani 1 1 d . . . H35 H 0.0683 0.6337 1.2043 0.047 Uiso 1 1 calc R . . C36 C 0.1625(3) 0.5246(3) 1.0747(2) 0.0326(6) Uani 1 1 d . . . H36 H 0.1186 0.4443 1.1019 0.039 Uiso 1 1 calc R . . C41 C 1.0228(3) 0.9591(2) 0.33529(19) 0.0257(5) Uani 1 1 d . . . C47 C 0.8921(3) 0.8918(2) 0.3974(2) 0.0271(5) Uani 1 1 d . . . O41 O 0.9575(2) 0.77211(19) 0.46150(16) 0.0396(5) Uani 1 1 d . . . H41 H 0.871(4) 0.740(3) 0.494(3) 0.048 Uiso 1 1 d . . . O42 O 0.7383(2) 0.94043(17) 0.38934(15) 0.0323(4) Uani 1 1 d . . . C42 C 0.9746(3) 1.0575(2) 0.2439(2) 0.0284(5) Uani 1 1 d . . . H42 H 0.8583 1.0814 0.2224 0.034 Uiso 1 1 calc R . . C43 C 1.0924(3) 1.1222(3) 0.1831(2) 0.0307(6) Uani 1 1 d . . . H43 H 1.0574 1.1895 0.1198 0.037 Uiso 1 1 calc R . . C44 C 1.2637(3) 1.0881(3) 0.2152(2) 0.0300(6) Uani 1 1 d . . . O44 O 1.3852(2) 1.1465(2) 0.15968(17) 0.0397(5) Uani 1 1 d . . . H44 H 1.340(4) 1.190(3) 0.095(3) 0.048 Uiso 1 1 d . . . C45 C 1.3120(3) 0.9896(3) 0.3080(2) 0.0320(6) Uani 1 1 d . . . H45 H 1.4274 0.9669 0.3312 0.038 Uiso 1 1 calc R . . C46 C 1.1927(3) 0.9249(3) 0.3663(2) 0.0296(5) Uani 1 1 d . . . H46 H 1.2273 0.8560 0.4287 0.035 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 N11 0.0311(11) 0.0286(11) 0.0285(11) -0.0040(8) 0.0040(8) -0.0116(9) C12 0.0250(11) 0.0307(13) 0.0292(13) -0.0021(10) 0.0036(9) -0.0106(10) N13 0.0333(11) 0.0286(11) 0.0414(13) 0.0016(10) 0.0027(9) -0.0105(9) C14 0.0387(15) 0.0254(13) 0.0537(17) -0.0083(12) 0.0077(12) -0.0116(11) C15 0.0392(14) 0.0333(14) 0.0412(15) -0.0141(12) 0.0067(11) -0.0152(12) N21 0.0371(12) 0.0331(12) 0.0330(12) 0.0025(9) 0.0037(9) -0.0114(10) C22 0.0326(13) 0.0346(14) 0.0382(15) 0.0009(11) 0.0036(11) -0.0025(11) C23 0.0372(14) 0.0275(13) 0.0374(14) 0.0036(11) -0.0009(11) -0.0079(11) C24 0.0328(13) 0.0297(13) 0.0214(12) -0.0025(10) -0.0015(9) -0.0093(10) C25 0.0349(13) 0.0289(13) 0.0310(13) -0.0049(11) 0.0031(10) -0.0018(10) C26 0.0418(15) 0.0289(13) 0.0340(14) -0.0013(11) 0.0008(11) -0.0095(11) C27 0.0326(13) 0.0340(13) 0.0282(13) -0.0012(10) -0.0019(10) -0.0098(11) C31 0.0248(11) 0.0293(12) 0.0275(12) -0.0029(10) -0.0014(9) -0.0073(9) C32 0.0272(12) 0.0333(13) 0.0308(13) -0.0052(11) 0.0005(10) -0.0095(10) C33 0.0330(13) 0.0339(14) 0.0399(15) -0.0060(11) -0.0023(11) -0.0108(11) C34 0.0370(14) 0.0429(16) 0.0443(16) -0.0190(13) -0.0007(12) -0.0100(12) C35 0.0336(14) 0.0544(17) 0.0328(15) -0.0144(13) 0.0052(11) -0.0125(12) C36 0.0290(12) 0.0408(14) 0.0300(13) -0.0035(11) 0.0027(10) -0.0137(11) C41 0.0281(12) 0.0229(12) 0.0266(12) -0.0077(10) 0.0016(9) -0.0054(9) C47 0.0301(13) 0.0227(12) 0.0286(13) -0.0061(10) 0.0002(10) -0.0056(10) O41 0.0314(10) 0.0353(10) 0.0465(12) 0.0097(9) 0.0067(8) -0.0072(8) O42 0.0272(9) 0.0290(9) 0.0398(10) -0.0015(8) 0.0005(7) -0.0065(7) C42 0.0288(12) 0.0258(12) 0.0303(13) -0.0044(10) -0.0019(10) -0.0047(10) C43 0.0325(13) 0.0274(12) 0.0304(13) 0.0014(10) -0.0012(10) -0.0062(10) C44 0.0307(12) 0.0297(13) 0.0315(13) -0.0071(10) 0.0021(10) -0.0098(10) O44 0.0313(10) 0.0465(12) 0.0411(11) 0.0067(9) 0.0011(8) -0.0157(8) C45 0.0270(12) 0.0325(13) 0.0372(14) -0.0032(11) -0.0039(10) -0.0080(10) C46 0.0337(13) 0.0288(13) 0.0257(13) -0.0025(10) -0.0025(10) -0.0066(10) _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 1.365(3) . ? N11 C15 1.367(3) . ? N11 C27 1.455(3) . ? C12 N13 1.321(3) . ? C12 C31 1.461(3) . ? N13 C14 1.367(3) . ? C14 C15 1.347(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? N21 C22 1.330(3) . ? N21 C26 1.332(3) . ? C22 C23 1.382(3) . ? C22 H22 0.9500 . ? C23 C24 1.379(4) . ? C23 H23 0.9500 . ? C24 C25 1.380(3) . ? C24 C27 1.511(3) . ? C25 C26 1.373(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C31 C32 1.396(3) . ? C31 C36 1.397(3) . ? C32 C33 1.376(3) . ? C32 H32 0.9500 . ? C33 C34 1.380(4) . ? C33 H33 0.9500 . ? C34 C35 1.380(4) . ? C34 H34 0.9500 . ? C35 C36 1.365(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.376(3) . ? C41 C46 1.386(3) . ? C41 C47 1.481(3) . ? C47 O42 1.214(3) . ? C47 O41 1.328(3) . ? O41 H41 0.87(3) . ? C42 C43 1.380(3) . ? C42 H42 0.9500 . ? C43 C44 1.401(3) . ? C43 H43 0.9500 . ? C44 O44 1.344(3) . ? C44 C45 1.388(3) . ? O44 H44 0.89(3) . ? C45 C46 1.377(3) . ? C45 H45 0.9500 . ? C46 H46 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 C12 N11 C15 107.4(2) . . ? C12 N11 C27 128.5(2) . . ? C15 N11 C27 123.9(2) . . ? N13 C12 N11 109.8(2) . . ? N13 C12 C31 124.3(2) . . ? N11 C12 C31 125.9(2) . . ? C12 N13 C14 106.6(2) . . ? C15 C14 N13 109.9(2) . . ? C15 C14 H14 125.0 . . ? N13 C14 H14 125.0 . . ? C14 C15 N11 106.3(2) . . ? C14 C15 H15 126.8 . . ? N11 C15 H15 126.8 . . ? C22 N21 C26 117.3(2) . . ? N21 C22 C23 123.4(3) . . ? N21 C22 H22 118.3 . . ? C23 C22 H22 118.3 . . ? C24 C23 C22 119.1(2) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C23 C24 C25 117.5(2) . . ? C23 C24 C27 123.1(2) . . ? C25 C24 C27 119.4(2) . . ? C26 C25 C24 119.9(2) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? N21 C26 C25 122.9(2) . . ? N21 C26 H26 118.5 . . ? C25 C26 H26 118.5 . . ? N11 C27 C24 114.0(2) . . ? N11 C27 H27A 108.8 . . ? C24 C27 H27A 108.8 . . ? N11 C27 H27B 108.8 . . ? C24 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C32 C31 C36 118.5(2) . . ? C32 C31 C12 122.5(2) . . ? C36 C31 C12 118.9(2) . . ? C33 C32 C31 120.0(2) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.7(2) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C33 C34 C35 119.4(3) . . ? C33 C34 H34 120.3 . . ? C35 C34 H34 120.3 . . ? C36 C35 C34 120.6(2) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 120.7(2) . . ? C35 C36 H36 119.7 . . ? C31 C36 H36 119.7 . . ? C42 C41 C46 119.1(2) . . ? C42 C41 C47 119.1(2) . . ? C46 C41 C47 121.8(2) . . ? O42 C47 O41 122.8(2) . . ? O42 C47 C41 123.0(2) . . ? O41 C47 C41 114.2(2) . . ? C47 O41 H41 107(2) . . ? C41 C42 C43 121.1(2) . . ? C41 C42 H42 119.4 . . ? C43 C42 H42 119.4 . . ? C42 C43 C44 119.6(2) . . ? C42 C43 H43 120.2 . . ? C44 C43 H43 120.2 . . ? O44 C44 C45 117.9(2) . . ? O44 C44 C43 122.8(2) . . ? C45 C44 C43 119.3(2) . . ? C44 O44 H44 105.9(19) . . ? C46 C45 C44 120.0(2) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C41 120.8(2) . . ? C45 C46 H46 119.6 . . ? C41 C46 H46 119.6 . . ? 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 C15 N11 C12 N13 -0.5(3) . . . . ? C27 N11 C12 N13 174.1(2) . . . . ? C15 N11 C12 C31 -179.4(2) . . . . ? C27 N11 C12 C31 -4.8(4) . . . . ? N11 C12 N13 C14 0.4(3) . . . . ? C31 C12 N13 C14 179.4(2) . . . . ? C12 N13 C14 C15 -0.2(3) . . . . ? N13 C14 C15 N11 -0.1(3) . . . . ? C12 N11 C15 C14 0.3(3) . . . . ? C27 N11 C15 C14 -174.6(2) . . . . ? C26 N21 C22 C23 -0.8(4) . . . . ? N21 C22 C23 C24 0.8(4) . . . . ? C22 C23 C24 C25 -0.9(4) . . . . ? C22 C23 C24 C27 177.6(2) . . . . ? C23 C24 C25 C26 1.0(4) . . . . ? C27 C24 C25 C26 -177.5(2) . . . . ? C22 N21 C26 C25 1.0(4) . . . . ? C24 C25 C26 N21 -1.1(4) . . . . ? C12 N11 C27 C24 98.9(3) . . . . ? C15 N11 C27 C24 -87.3(3) . . . . ? C23 C24 C27 N11 28.5(3) . . . . ? C25 C24 C27 N11 -153.0(2) . . . . ? N13 C12 C31 C32 144.0(2) . . . . ? N11 C12 C31 C32 -37.2(4) . . . . ? N13 C12 C31 C36 -34.8(3) . . . . ? N11 C12 C31 C36 144.0(2) . . . . ? C36 C31 C32 C33 -2.2(4) . . . . ? C12 C31 C32 C33 179.0(2) . . . . ? C31 C32 C33 C34 1.2(4) . . . . ? C32 C33 C34 C35 0.0(4) . . . . ? C33 C34 C35 C36 -0.3(4) . . . . ? C34 C35 C36 C31 -0.7(4) . . . . ? C32 C31 C36 C35 1.9(4) . . . . ? C12 C31 C36 C35 -179.2(2) . . . . ? C42 C41 C47 O42 -17.6(4) . . . . ? C46 C41 C47 O42 162.8(2) . . . . ? C42 C41 C47 O41 161.3(2) . . . . ? C46 C41 C47 O41 -18.3(3) . . . . ? C46 C41 C42 C43 0.1(4) . . . . ? C47 C41 C42 C43 -179.6(2) . . . . ? C41 C42 C43 C44 -0.5(4) . . . . ? C42 C43 C44 O44 179.8(2) . . . . ? C42 C43 C44 C45 -0.1(4) . . . . ? O44 C44 C45 C46 -178.8(2) . . . . ? C43 C44 C45 C46 1.1(4) . . . . ? C44 C45 C46 C41 -1.5(4) . . . . ? C42 C41 C46 C45 0.9(4) . . . . ? C47 C41 C46 C45 -179.4(2) . . . . ? 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 O41 H41 N21 0.87(3) 1.82(3) 2.693(2) 174(3) . O44 H44 N13 0.89(3) 1.78(3) 2.659(3) 166(3) 1_664 _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.447 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.099 #END data_39 _database_code_depnum_ccdc_archive 'CCDC 652593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 442 1-[(4-pyridyl)methyl]-5,6-dimethylbenzimidazole, 4-bromoPhC(CN)(=NOH) ; _chemical_name_common ;442 1-((4-pyridyl)methyl)-5,6-dimethylbenzimidazole, 4- bromoPhC(CN)(=NOH) ; _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 Br N5 O' _chemical_formula_sum 'C23 H20 Br N5 O' _chemical_formula_weight 462.35 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 15.9510(15) _cell_length_b 5.9914(6) _cell_length_c 23.071(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.494(4) _cell_angle_gamma 90.00 _cell_volume 2144.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 9865 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 30.82 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5935 _exptl_absorpt_correction_T_max 0.7594 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 81141 _diffrn_reflns_av_R_equivalents 0.0453 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 33.14 _reflns_number_total 8148 _reflns_number_gt 6008 _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^)+(0.0520P)^2^+0.4100P] 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 8148 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1001 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 Br1 Br -0.167241(9) 0.09022(3) 0.629719(8) 0.04513(7) Uani 1 1 d . . . N11 N 0.45081(6) 1.14130(17) 0.65915(4) 0.02060(19) Uani 1 1 d . . . C12 C 0.45731(8) 0.9526(2) 0.69237(5) 0.0232(2) Uani 1 1 d . . . N13 N 0.38422(7) 0.84072(19) 0.68400(4) 0.0245(2) Uani 1 1 d . . . C14 C 0.32566(7) 0.9644(2) 0.64201(5) 0.0212(2) Uani 1 1 d . . . C15 C 0.23899(8) 0.9233(2) 0.61529(5) 0.0243(2) Uani 1 1 d . . . H15 H 0.2106 0.7957 0.6260 0.029 Uiso 1 1 calc R . . C16 C 0.19538(8) 1.0719(2) 0.57296(6) 0.0254(2) Uani 1 1 d . . . C17 C 0.23799(8) 1.2638(2) 0.55716(5) 0.0250(2) Uani 1 1 d . . . C18 C 0.32405(8) 1.3053(2) 0.58363(5) 0.0228(2) Uani 1 1 d . . . H18 H 0.3528 1.4330 0.5733 0.027 Uiso 1 1 calc R . . H12 H 0.5109 0.9017 0.7192 0.027 Uiso 1 1 d R . . C19 C 0.36658(7) 1.1531(2) 0.62576(5) 0.0198(2) Uani 1 1 d . . . C20 C 0.10259(9) 1.0273(3) 0.54278(7) 0.0351(3) Uani 1 1 d . . . H20A H 0.0833 0.8908 0.5591 0.053 Uiso 1 1 calc R . . H20B H 0.0971 1.0088 0.4999 0.053 Uiso 1 1 calc R . . H20C H 0.0669 1.1532 0.5497 0.053 Uiso 1 1 calc R . . C21 C 0.18995(10) 1.4208(2) 0.50992(7) 0.0367(3) Uani 1 1 d . . . H21A H 0.1412 1.4864 0.5230 0.055 Uiso 1 1 calc R . . H21B H 0.1686 1.3384 0.4727 0.055 Uiso 1 1 calc R . . H21C H 0.2288 1.5397 0.5033 0.055 Uiso 1 1 calc R . . N31 N 0.60277(9) 1.3253(2) 0.51238(5) 0.0348(3) Uani 1 1 d . . . C32 C 0.56623(9) 1.3679(2) 0.55764(6) 0.0271(2) Uani 1 1 d . . . H32 H 0.5430 1.5127 0.5600 0.033 Uiso 1 1 calc R . . C33 C 0.55995(7) 1.21543(19) 0.60128(5) 0.0191(2) Uani 1 1 d . . . C34 C 0.59228(9) 1.0031(2) 0.59693(6) 0.0275(2) Uani 1 1 d . . . H34 H 0.5890 0.8924 0.6258 0.033 Uiso 1 1 calc R . . C35 C 0.62942(9) 0.9548(2) 0.54978(7) 0.0297(3) Uani 1 1 d . . . H35 H 0.6515 0.8100 0.5455 0.036 Uiso 1 1 calc R . . C36 C 0.63376(9) 1.1206(2) 0.50924(6) 0.0292(3) Uani 1 1 d . . . H36 H 0.6602 1.0871 0.4774 0.035 Uiso 1 1 calc R . . C37 C 0.52251(7) 1.2844(2) 0.65275(5) 0.0216(2) Uani 1 1 d . . . H37A H 0.5683 1.2788 0.6900 0.026 Uiso 1 1 calc R . . H37B H 0.5020 1.4406 0.6467 0.026 Uiso 1 1 calc R . . C41 C 0.12472(7) 0.2484(2) 0.70414(5) 0.0214(2) Uani 1 1 d . . . C42 C 0.09034(8) 0.0458(2) 0.71731(6) 0.0261(2) Uani 1 1 d . . . H42 H 0.1265 -0.0602 0.7418 0.031 Uiso 1 1 calc R . . C43 C 0.00345(9) -0.0025(2) 0.69495(6) 0.0290(3) Uani 1 1 d . . . H43 H -0.0197 -0.1408 0.7040 0.035 Uiso 1 1 calc R . . C44 C -0.04874(8) 0.1527(2) 0.65951(6) 0.0290(3) Uani 1 1 d . . . C45 C -0.01579(9) 0.3558(2) 0.64577(6) 0.0305(3) Uani 1 1 d . . . H45 H -0.0522 0.4615 0.6214 0.037 Uiso 1 1 calc R . . C46 C 0.07058(8) 0.4019(2) 0.66797(6) 0.0271(2) Uani 1 1 d . . . H46 H 0.0935 0.5399 0.6585 0.033 Uiso 1 1 calc R . . C47 C 0.21663(7) 0.2978(2) 0.72780(5) 0.0215(2) Uani 1 1 d . . . N47 N 0.25152(7) 0.46869(18) 0.70874(5) 0.0236(2) Uani 1 1 d . . . O47 O 0.33737(6) 0.48907(17) 0.73532(4) 0.02741(19) Uani 1 1 d . . . H47 H 0.3521(12) 0.613(3) 0.7174(8) 0.033 Uiso 1 1 d . . . C48 C 0.26670(8) 0.1542(2) 0.77307(6) 0.0280(3) Uani 1 1 d . . . N48 N 0.30584(9) 0.0437(2) 0.80988(7) 0.0448(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 0.02128(8) 0.06025(12) 0.05077(11) -0.00289(7) 0.00212(6) -0.01034(6) N11 0.0164(4) 0.0268(5) 0.0186(4) 0.0001(4) 0.0040(3) -0.0054(4) C12 0.0187(5) 0.0317(6) 0.0186(5) 0.0037(4) 0.0031(4) -0.0048(4) N13 0.0193(5) 0.0324(5) 0.0208(4) 0.0052(4) 0.0027(4) -0.0057(4) C14 0.0171(5) 0.0291(6) 0.0175(5) 0.0000(4) 0.0042(4) -0.0035(4) C15 0.0176(5) 0.0326(6) 0.0230(5) -0.0016(5) 0.0053(4) -0.0063(4) C16 0.0163(5) 0.0354(7) 0.0238(5) -0.0045(5) 0.0029(4) -0.0006(4) C17 0.0221(5) 0.0283(6) 0.0231(5) -0.0022(4) 0.0025(4) 0.0032(5) C18 0.0211(5) 0.0244(5) 0.0228(5) -0.0007(4) 0.0051(4) -0.0007(4) C19 0.0159(5) 0.0257(5) 0.0178(5) -0.0023(4) 0.0042(4) -0.0035(4) C20 0.0190(6) 0.0471(8) 0.0352(7) -0.0036(6) -0.0014(5) -0.0027(5) C21 0.0313(7) 0.0361(7) 0.0376(7) 0.0044(6) -0.0021(6) 0.0065(6) N31 0.0484(8) 0.0324(6) 0.0289(6) 0.0057(5) 0.0196(5) 0.0016(5) C32 0.0351(7) 0.0233(6) 0.0250(5) 0.0017(5) 0.0112(5) 0.0011(5) C33 0.0166(5) 0.0221(5) 0.0182(4) -0.0021(4) 0.0032(4) -0.0059(4) C34 0.0295(6) 0.0239(6) 0.0318(6) 0.0040(5) 0.0126(5) -0.0017(5) C35 0.0302(7) 0.0239(6) 0.0383(7) -0.0034(5) 0.0150(6) -0.0019(5) C36 0.0314(7) 0.0330(7) 0.0266(6) -0.0054(5) 0.0136(5) -0.0050(5) C37 0.0189(5) 0.0257(5) 0.0207(5) -0.0031(4) 0.0058(4) -0.0076(4) C41 0.0174(5) 0.0226(5) 0.0248(5) 0.0010(4) 0.0061(4) -0.0003(4) C42 0.0227(6) 0.0231(6) 0.0336(6) 0.0034(5) 0.0086(5) 0.0003(4) C43 0.0251(6) 0.0266(6) 0.0374(7) -0.0006(5) 0.0112(5) -0.0057(5) C44 0.0199(6) 0.0363(7) 0.0308(6) -0.0037(5) 0.0063(5) -0.0038(5) C45 0.0210(6) 0.0351(7) 0.0331(6) 0.0054(5) 0.0017(5) 0.0010(5) C46 0.0213(5) 0.0256(6) 0.0333(6) 0.0070(5) 0.0040(5) -0.0014(4) C47 0.0180(5) 0.0216(5) 0.0251(5) 0.0020(4) 0.0053(4) 0.0019(4) N47 0.0178(5) 0.0275(5) 0.0244(5) 0.0014(4) 0.0028(4) -0.0018(4) O47 0.0182(4) 0.0323(5) 0.0292(4) 0.0055(4) 0.0004(3) -0.0051(3) C48 0.0201(5) 0.0266(6) 0.0368(7) 0.0049(5) 0.0055(5) 0.0014(5) N48 0.0335(7) 0.0414(7) 0.0554(8) 0.0183(6) 0.0019(6) 0.0078(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 C44 1.8918(13) . ? N11 C12 1.3561(16) . ? N11 C19 1.3859(15) . ? N11 C37 1.4641(15) . ? C12 N13 1.3195(15) . ? C12 H12 0.9803 . ? N13 C14 1.3921(16) . ? C14 C15 1.3979(16) . ? C14 C19 1.3998(17) . ? C15 C16 1.3835(18) . ? C15 H15 0.9500 . ? C16 C17 1.4257(19) . ? C16 C20 1.5054(18) . ? C17 C18 1.3884(17) . ? C17 C21 1.5065(18) . ? C18 C19 1.3885(17) . ? 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 1.3308(19) . ? N31 C32 1.3338(17) . ? C32 C33 1.3801(17) . ? C32 H32 0.9500 . ? C33 C34 1.3852(18) . ? C33 C37 1.5062(16) . ? C34 C35 1.3852(19) . ? C34 H34 0.9500 . ? C35 C36 1.377(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C41 C42 1.3944(17) . ? C41 C46 1.3972(17) . ? C41 C47 1.4701(16) . ? C42 C43 1.3919(18) . ? C42 H42 0.9500 . ? C43 C44 1.381(2) . ? C43 H43 0.9500 . ? C44 C45 1.391(2) . ? C45 C46 1.3809(18) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 N47 1.2907(16) . ? C47 C48 1.4421(17) . ? N47 O47 1.3690(13) . ? O47 H47 0.907(18) . ? C48 N48 1.1407(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C19 107.05(10) . . ? C12 N11 C37 125.92(10) . . ? C19 N11 C37 126.35(10) . . ? N13 C12 N11 113.11(11) . . ? N13 C12 H12 123.0 . . ? N11 C12 H12 123.8 . . ? C12 N13 C14 104.94(10) . . ? N13 C14 C15 130.31(11) . . ? N13 C14 C19 109.71(10) . . ? C15 C14 C19 119.95(11) . . ? C16 C15 C14 118.72(11) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 120.56(11) . . ? C15 C16 C20 119.37(12) . . ? C17 C16 C20 120.07(12) . . ? C18 C17 C16 120.88(11) . . ? C18 C17 C21 119.36(12) . . ? C16 C17 C21 119.73(12) . . ? C17 C18 C19 117.51(11) . . ? C17 C18 H18 121.2 . . ? C19 C18 H18 121.2 . . ? N11 C19 C18 132.42(11) . . ? N11 C19 C14 105.19(10) . . ? C18 C19 C14 122.38(11) . . ? 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 117.03(12) . . ? N31 C32 C33 124.33(12) . . ? N31 C32 H32 117.8 . . ? C33 C32 H32 117.8 . . ? C32 C33 C34 117.59(11) . . ? C32 C33 C37 120.21(11) . . ? C34 C33 C37 122.14(11) . . ? C35 C34 C33 118.92(12) . . ? C35 C34 H34 120.5 . . ? C33 C34 H34 120.5 . . ? C36 C35 C34 118.75(13) . . ? C36 C35 H35 120.6 . . ? C34 C35 H35 120.6 . . ? N31 C36 C35 123.35(12) . . ? N31 C36 H36 118.3 . . ? C35 C36 H36 118.3 . . ? N11 C37 C33 112.42(9) . . ? N11 C37 H37A 109.1 . . ? C33 C37 H37A 109.1 . . ? N11 C37 H37B 109.1 . . ? C33 C37 H37B 109.1 . . ? H37A C37 H37B 107.9 . . ? C42 C41 C46 118.91(11) . . ? C42 C41 C47 120.21(11) . . ? C46 C41 C47 120.87(11) . . ? C43 C42 C41 120.56(12) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? C44 C43 C42 119.34(12) . . ? C44 C43 H43 120.3 . . ? C42 C43 H43 120.3 . . ? C43 C44 C45 121.07(12) . . ? C43 C44 Br1 119.67(10) . . ? C45 C44 Br1 119.26(10) . . ? C46 C45 C44 119.18(12) . . ? C46 C45 H45 120.4 . . ? C44 C45 H45 120.4 . . ? C45 C46 C41 120.94(12) . . ? C45 C46 H46 119.5 . . ? C41 C46 H46 119.5 . . ? N47 C47 C48 120.67(11) . . ? N47 C47 C41 120.35(11) . . ? C48 C47 C41 118.98(11) . . ? C47 N47 O47 112.58(10) . . ? N47 O47 H47 102.0(12) . . ? N48 C48 C47 178.38(17) . . ? 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 -0.58(14) . . . . ? C37 N11 C12 N13 -171.60(11) . . . . ? N11 C12 N13 C14 0.31(15) . . . . ? C12 N13 C14 C15 178.34(13) . . . . ? C12 N13 C14 C19 0.08(14) . . . . ? N13 C14 C15 C16 -178.09(13) . . . . ? C19 C14 C15 C16 0.02(18) . . . . ? C14 C15 C16 C17 -0.30(19) . . . . ? C14 C15 C16 C20 178.64(12) . . . . ? C15 C16 C17 C18 0.26(19) . . . . ? C20 C16 C17 C18 -178.67(12) . . . . ? C15 C16 C17 C21 178.57(13) . . . . ? C20 C16 C17 C21 -0.36(19) . . . . ? C16 C17 C18 C19 0.07(18) . . . . ? C21 C17 C18 C19 -178.25(12) . . . . ? C12 N11 C19 C18 -178.51(13) . . . . ? C37 N11 C19 C18 -7.5(2) . . . . ? C12 N11 C19 C14 0.58(13) . . . . ? C37 N11 C19 C14 171.55(11) . . . . ? C17 C18 C19 N11 178.60(12) . . . . ? C17 C18 C19 C14 -0.37(18) . . . . ? N13 C14 C19 N11 -0.41(13) . . . . ? C15 C14 C19 N11 -178.88(11) . . . . ? N13 C14 C19 C18 178.80(11) . . . . ? C15 C14 C19 C18 0.33(19) . . . . ? C36 N31 C32 C33 1.0(2) . . . . ? N31 C32 C33 C34 -1.4(2) . . . . ? N31 C32 C33 C37 176.08(13) . . . . ? C32 C33 C34 C35 0.40(19) . . . . ? C37 C33 C34 C35 -176.99(12) . . . . ? C33 C34 C35 C36 0.7(2) . . . . ? C32 N31 C36 C35 0.2(2) . . . . ? C34 C35 C36 N31 -1.1(2) . . . . ? C12 N11 C37 C33 90.08(14) . . . . ? C19 N11 C37 C33 -79.24(15) . . . . ? C32 C33 C37 N11 125.19(12) . . . . ? C34 C33 C37 N11 -57.48(15) . . . . ? C46 C41 C42 C43 -0.21(19) . . . . ? C47 C41 C42 C43 -179.83(12) . . . . ? C41 C42 C43 C44 -0.1(2) . . . . ? C42 C43 C44 C45 0.1(2) . . . . ? C42 C43 C44 Br1 -179.21(10) . . . . ? C43 C44 C45 C46 0.1(2) . . . . ? Br1 C44 C45 C46 179.47(11) . . . . ? C44 C45 C46 C41 -0.4(2) . . . . ? C42 C41 C46 C45 0.5(2) . . . . ? C47 C41 C46 C45 -179.92(12) . . . . ? C42 C41 C47 N47 169.57(12) . . . . ? C46 C41 C47 N47 -10.04(18) . . . . ? C42 C41 C47 C48 -11.22(18) . . . . ? C46 C41 C47 C48 169.17(12) . . . . ? C48 C47 N47 O47 1.02(17) . . . . ? C41 C47 N47 O47 -179.78(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 O47 H47 N13 0.907(18) 1.704(18) 2.6100(15) 177.6(17) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.789 _refine_diff_density_min -0.522 _refine_diff_density_rms 0.060