Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1048 _publ_requested_journal 'Green Chemistry' _publ_section_title ; Preparation of Benzimidaoles in High-Temperature Water ; _publ_contact_author_name 'Martyn Poliakoff' _publ_contact_author_email martyn.poliakoff@nottingham.ac.uk _publ_contact_author_address ; School of Chemistry University of Nottingham University Park Nottingham NG7 2RD ; loop_ _publ_author_name 'Lucinda Dudd' 'Eleni Venardou' 'Eduardo Garcia-Verdugo' 'Peter Licence' 'Alexander J. Blake' 'Claire Wilson' 'Martyn Poliakoff' data_imphpr _database_code_CSD 200134 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 N4' _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 8.5187(9) _cell_length_b 9.8623(11) _cell_length_c 14.8684(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1249.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1524 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 28.8 _exptl_crystal_description 'plate cut from large block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.087 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5853 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 28.85 _reflns_number_total 1712 _reflns_number_gt 1012 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2001)' _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^)+(0.0431P)^2^+0.2665P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, NH located deltaF' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1477 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N1 N 0.24009(14) 0.61669(11) 0.06126(8) 0.0198(3) Uani 1 1 d . . . C2 C 0.28298(16) 0.49449(14) 0.03383(10) 0.0186(3) Uani 1 1 d . . . N3 N 0.18177(13) 0.39548(12) 0.05999(8) 0.0190(3) Uani 1 1 d . . . H3 H 0.1897 0.3084 0.0479 0.023 Uiso 1 1 calc R . . C3A C 0.06395(16) 0.45740(14) 0.10915(10) 0.0182(3) Uani 1 1 d . . . C4 C -0.06586(17) 0.40569(16) 0.15456(10) 0.0230(4) Uani 1 1 d . . . H4 H -0.0912 0.3119 0.1528 0.028 Uiso 1 1 calc R . . C5 C -0.15626(17) 0.49749(16) 0.20239(10) 0.0255(4) Uani 1 1 d . . . H5 H -0.2454 0.4662 0.2347 0.031 Uiso 1 1 calc R . . C6 C -0.11835(18) 0.63634(16) 0.20397(10) 0.0255(4) Uani 1 1 d . . . H6 H -0.1822 0.6966 0.2378 0.031 Uiso 1 1 calc R . . C7A C 0.10180(16) 0.59575(14) 0.10962(10) 0.0184(3) Uani 1 1 d . . . C7 C 0.00905(17) 0.68728(15) 0.15767(11) 0.0231(4) Uani 1 1 d . . . H7 H 0.0328 0.7814 0.1585 0.028 Uiso 1 1 calc R . . C8 C 0.42779(16) 0.46338(15) -0.01873(11) 0.0217(4) Uani 1 1 d . . . H8B H 0.4118 0.4907 -0.0821 0.026 Uiso 1 1 calc R . . H8A H 0.4467 0.3643 -0.0176 0.026 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 N1 0.0188(6) 0.0175(6) 0.0230(7) -0.0019(5) 0.0012(5) 0.0007(5) C2 0.0169(7) 0.0184(7) 0.0206(8) -0.0011(6) -0.0037(6) -0.0008(5) N3 0.0174(6) 0.0146(6) 0.0249(7) -0.0022(5) 0.0004(5) 0.0003(4) C3A 0.0171(7) 0.0192(7) 0.0183(8) -0.0007(6) -0.0034(6) 0.0022(6) C4 0.0222(8) 0.0214(7) 0.0253(9) 0.0022(6) -0.0009(7) -0.0017(6) C5 0.0213(8) 0.0318(8) 0.0233(9) 0.0027(7) 0.0034(7) -0.0011(7) C6 0.0236(8) 0.0280(8) 0.0249(9) -0.0029(7) 0.0019(7) 0.0073(7) C7A 0.0172(7) 0.0188(7) 0.0192(8) 0.0004(6) -0.0024(6) 0.0007(6) C7 0.0232(8) 0.0186(7) 0.0275(9) -0.0017(6) -0.0025(7) 0.0028(6) C8 0.0186(7) 0.0209(7) 0.0258(9) -0.0045(6) 0.0016(6) -0.0001(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 N1 C2 1.3238(17) . ? N1 C7A 1.3955(18) . ? C2 N3 1.3594(18) . ? C2 C8 1.492(2) . ? N3 C3A 1.3836(18) . ? C3A C4 1.392(2) . ? C3A C7A 1.402(2) . ? C4 C5 1.385(2) . ? C5 C6 1.407(2) . ? C6 C7 1.380(2) . ? C7A C7 1.396(2) . ? C8 C8 1.532(3) 5_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C7A 104.89(11) . . ? N1 C2 N3 113.00(12) . . ? N1 C2 C8 125.22(13) . . ? N3 C2 C8 121.77(13) . . ? C2 N3 C3A 107.11(12) . . ? N3 C3A C4 132.12(14) . . ? N3 C3A C7A 105.39(12) . . ? C4 C3A C7A 122.45(14) . . ? C5 C4 C3A 116.82(14) . . ? C4 C5 C6 121.14(14) . . ? C7 C6 C5 121.77(14) . . ? N1 C7A C7 130.21(13) . . ? N1 C7A C3A 109.61(12) . . ? C7 C7A C3A 120.11(13) . . ? C6 C7 C7A 117.70(14) . . ? C2 C8 C8 112.12(15) . 5_665 ? 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 N3 H3 N1 0.88 1.99 2.8290(16) 158.2 8_655 _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.230 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.045 ##END======== data_imphbz _database_code_CSD 200135 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H14 N4' _chemical_formula_weight 310.35 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' _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 7.5866(11) _cell_length_b 10.366(2) _cell_length_c 9.7278(15) _cell_angle_alpha 90.00 _cell_angle_beta 107.895(2) _cell_angle_gamma 90.00 _cell_volume 727.97(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1531 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.6 _exptl_crystal_description tablet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.52 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.087 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5627 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.15 _reflns_number_total 1738 _reflns_number_gt 1194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97; PLATON (Spek, 2001)' _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^)+(0.0527P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'CH geometrically placed, NH from delta-F' _refine_ls_hydrogen_treatment 'riding model, NH refined' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1642 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.0977 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 N1 N 0.69928(17) 0.20268(12) 0.21240(13) 0.0216(3) Uani 1 1 d . . . C2 C 0.64856(19) 0.24691(14) 0.07424(15) 0.0200(3) Uani 1 1 d . . . N3 N 0.67698(17) 0.16302(11) -0.01955(13) 0.0225(3) Uani 1 1 d . . . C3A C 0.7505(2) 0.05479(14) 0.06470(15) 0.0218(3) Uani 1 1 d . . . C4 C 0.8065(2) -0.06433(14) 0.02507(17) 0.0256(4) Uani 1 1 d . . . H4A H 0.7967 -0.0827 -0.0727 0.031 Uiso 1 1 calc R . . C5 C 0.8765(2) -0.15444(14) 0.13276(17) 0.0258(4) Uani 1 1 d . . . H5A H 0.9172 -0.2355 0.1084 0.031 Uiso 1 1 calc R . . C6 C 0.8888(2) -0.12933(14) 0.27632(17) 0.0261(4) Uani 1 1 d . . . H6A H 0.9366 -0.1940 0.3471 0.031 Uiso 1 1 calc R . . C7 C 0.8333(2) -0.01285(14) 0.31804(17) 0.0254(4) Uani 1 1 d . . . H7A H 0.8412 0.0043 0.4157 0.031 Uiso 1 1 calc R . . C7A C 0.76510(19) 0.07848(13) 0.20917(16) 0.0210(3) Uani 1 1 d . . . C8 C 0.5712(2) 0.37642(13) 0.03634(15) 0.0203(3) Uani 1 1 d . . . C9 C 0.6279(2) 0.47765(14) 0.13451(16) 0.0222(4) Uani 1 1 d . . . H9A H 0.7155 0.4622 0.2265 0.027 Uiso 1 1 calc R . . C10 C 0.5572(2) 0.60041(14) 0.09842(16) 0.0213(3) Uani 1 1 d . . . H10A H 0.5963 0.6690 0.1657 0.026 Uiso 1 1 calc R . . H1 H 0.690(2) 0.2463(15) 0.2955(18) 0.034(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0263(7) 0.0201(7) 0.0183(7) -0.0001(5) 0.0069(5) 0.0020(5) C2 0.0218(7) 0.0191(8) 0.0198(8) 0.0001(6) 0.0074(6) -0.0027(6) N3 0.0298(7) 0.0174(6) 0.0212(7) 0.0001(5) 0.0090(5) 0.0019(5) C3A 0.0250(8) 0.0181(8) 0.0220(8) 0.0020(6) 0.0070(6) -0.0005(6) C4 0.0340(9) 0.0206(8) 0.0233(8) -0.0009(6) 0.0104(7) 0.0013(7) C5 0.0282(8) 0.0193(8) 0.0305(9) 0.0005(6) 0.0100(7) 0.0035(7) C6 0.0271(8) 0.0213(8) 0.0290(9) 0.0080(6) 0.0072(7) 0.0034(6) C7 0.0284(8) 0.0263(9) 0.0212(8) 0.0035(6) 0.0070(6) 0.0015(7) C7A 0.0212(7) 0.0181(8) 0.0236(8) 0.0003(6) 0.0067(6) -0.0006(6) C8 0.0245(7) 0.0177(8) 0.0214(8) 0.0001(6) 0.0112(6) -0.0007(6) C9 0.0243(8) 0.0231(8) 0.0187(8) -0.0002(6) 0.0057(6) -0.0003(6) C10 0.0260(8) 0.0178(7) 0.0211(8) -0.0038(6) 0.0086(6) -0.0013(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 N1 C2 1.3589(18) . ? N1 C7A 1.3847(18) . ? C2 N3 1.3251(18) . ? C2 C8 1.466(2) . ? N3 C3A 1.4002(18) . ? C3A C7A 1.397(2) . ? C3A C4 1.398(2) . ? C4 C5 1.382(2) . ? C5 C6 1.395(2) . ? C6 C7 1.380(2) . ? C7 C7A 1.396(2) . ? C8 C10 1.393(2) 3_665 ? C8 C9 1.3949(19) . ? C9 C10 1.384(2) . ? C10 C8 1.393(2) 3_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C7A 106.60(12) . . ? N3 C2 N1 113.77(13) . . ? N3 C2 C8 124.40(13) . . ? N1 C2 C8 121.83(13) . . ? C2 N3 C3A 104.04(12) . . ? C7A C3A C4 119.72(13) . . ? C7A C3A N3 110.01(13) . . ? C4 C3A N3 130.27(14) . . ? C5 C4 C3A 117.80(14) . . ? C4 C5 C6 121.64(14) . . ? C7 C6 C5 121.66(14) . . ? C6 C7 C7A 116.47(14) . . ? N1 C7A C7 131.72(14) . . ? N1 C7A C3A 105.58(12) . . ? C7 C7A C3A 122.70(14) . . ? C10 C8 C9 119.62(13) 3_665 . ? C10 C8 C2 120.31(13) 3_665 . ? C9 C8 C2 120.06(13) . . ? C10 C9 C8 120.26(13) . . ? C9 C10 C8 120.12(13) . 3_665 ? 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 N1 H1 N3 0.946(17) 2.060(17) 3.0062(18) 178.1(15) 4_566 _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.225 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.041 #END==== data_BZIMPH _database_code_CSD 200136 _refine_special_details ; One H atom is statistically disordered, being bonded to N1 or N3. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 N4' _chemical_formula_sum 'C20 H14 N4' _chemical_formula_weight 310.35 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.712(2) _cell_length_b 8.7976(8) _cell_length_c 9.7375(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1517.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3208 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.7 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.084 _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 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13932 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_reflns_av_sigmaI/netI 0.040 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 28.81 _reflns_number_total 1857 _reflns_number_gt 1305 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2002)' _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^)+(0.048P)^2^+0.095P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1857 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0974 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_restrained_S_all 1.03 _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 N1 N 0.40792(6) 0.08019(11) 0.23037(10) 0.0219(3) Uani 1 1 d . . . H1 H 0.4180 0.0735 0.1421 0.026 Uiso 0.50 1 calc PR . . C2 C 0.42969(7) -0.01615(14) 0.32951(12) 0.0219(3) Uani 1 1 d . . . N3 N 0.40585(6) 0.02509(12) 0.45483(10) 0.0237(3) Uani 1 1 d . . . H3 H 0.4141 -0.0226 0.5328 0.028 Uiso 0.50 1 calc PR . . C3A C 0.36543(7) 0.15842(14) 0.43585(13) 0.0225(3) Uani 1 1 d . . . C4 C 0.32664(7) 0.25038(16) 0.52912(13) 0.0274(3) Uani 1 1 d . . . H4 H 0.3270 0.2294 0.6248 0.033 Uiso 1 1 calc R . . C5 C 0.28772(7) 0.37318(16) 0.47619(14) 0.0302(3) Uani 1 1 d . . . H5 H 0.2599 0.4366 0.5368 0.036 Uiso 1 1 calc R . . C6 C 0.28812(7) 0.40664(16) 0.33609(14) 0.0293(3) Uani 1 1 d . . . H6 H 0.2607 0.4922 0.3037 0.035 Uiso 1 1 calc R . . C7 C 0.32756(7) 0.31810(14) 0.24341(14) 0.0260(3) Uani 1 1 d . . . H7 H 0.3283 0.3418 0.1482 0.031 Uiso 1 1 calc R . . C7A C 0.36629(7) 0.19244(14) 0.29539(12) 0.0212(3) Uani 1 1 d . . . C8 C 0.46978(7) -0.15802(14) 0.29693(12) 0.0228(3) Uani 1 1 d . . . C9 C 0.44288(8) -0.29576(15) 0.34758(15) 0.0309(3) Uani 1 1 d . . . H9 H 0.4040 -0.2965 0.4148 0.037 Uiso 1 1 calc R . . C10 C 0.47261(8) -0.43210(15) 0.30031(16) 0.0382(4) Uani 1 1 d . . . H10 H 0.4552 -0.5256 0.3374 0.046 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 N1 0.0235(5) 0.0232(5) 0.0191(5) -0.0004(4) 0.0010(4) 0.0002(4) C2 0.0213(6) 0.0224(6) 0.0220(6) -0.0002(5) 0.0015(5) -0.0045(5) N3 0.0263(6) 0.0253(6) 0.0197(5) 0.0007(4) 0.0011(4) -0.0015(4) C3A 0.0211(6) 0.0236(6) 0.0229(6) -0.0005(5) -0.0017(5) -0.0044(5) C4 0.0265(6) 0.0340(8) 0.0218(6) -0.0033(6) 0.0011(5) -0.0021(6) C5 0.0257(7) 0.0333(8) 0.0316(7) -0.0096(6) 0.0022(6) 0.0035(6) C6 0.0259(7) 0.0281(7) 0.0340(7) -0.0020(6) -0.0032(6) 0.0058(6) C7 0.0263(7) 0.0283(7) 0.0234(6) 0.0016(5) -0.0018(5) 0.0007(5) C7A 0.0194(6) 0.0227(6) 0.0215(6) -0.0024(5) 0.0004(5) -0.0024(5) C8 0.0254(6) 0.0212(6) 0.0217(6) 0.0005(5) -0.0030(5) -0.0011(5) C9 0.0304(7) 0.0275(7) 0.0346(7) 0.0066(6) -0.0024(6) -0.0049(6) C10 0.0368(8) 0.0208(7) 0.0571(10) 0.0064(6) -0.0096(7) -0.0045(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 N1 C2 1.3412(15) . ? N1 C7A 1.3856(15) . ? C2 N3 1.3412(15) . ? C2 C8 1.4707(17) . ? N3 C3A 1.3867(16) . ? C3A C4 1.3969(17) . ? C3A C7A 1.4001(17) . ? C4 C5 1.3814(19) . ? C5 C6 1.3957(19) . ? C6 C7 1.3817(18) . ? C7 C7A 1.3960(18) . ? C8 C9 1.3924(18) . ? C8 C8 1.407(2) 3_655 ? C9 C10 1.389(2) . ? C10 C10 1.379(3) 3_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C7A 105.93(10) . . ? N3 C2 N1 113.17(11) . . ? N3 C2 C8 125.30(11) . . ? N1 C2 C8 121.32(11) . . ? C2 N3 C3A 105.67(10) . . ? N3 C3A C4 131.09(11) . . ? N3 C3A C7A 107.78(11) . . ? C4 C3A C7A 121.11(12) . . ? C5 C4 C3A 117.12(12) . . ? C4 C5 C6 121.81(12) . . ? C7 C6 C5 121.48(13) . . ? C6 C7 C7A 117.26(12) . . ? N1 C7A C7 131.32(11) . . ? N1 C7A C3A 107.44(11) . . ? C7 C7A C3A 121.21(11) . . ? C9 C8 C8 119.36(8) . 3_655 ? C9 C8 C2 119.80(11) . . ? C8 C8 C2 120.48(7) 3_655 . ? C10 C9 C8 120.31(13) . . ? C10 C10 C9 120.16(8) 3_655 . ? 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 C7A N1 C2 N3 -0.41(14) . . . . ? C7A N1 C2 C8 174.56(10) . . . . ? N1 C2 N3 C3A 0.04(14) . . . . ? C8 C2 N3 C3A -174.70(11) . . . . ? C2 N3 C3A C4 178.62(13) . . . . ? C2 N3 C3A C7A 0.34(13) . . . . ? N3 C3A C4 C5 -176.34(12) . . . . ? C7A C3A C4 C5 1.74(19) . . . . ? C3A C4 C5 C6 -1.32(19) . . . . ? C4 C5 C6 C7 0.1(2) . . . . ? C5 C6 C7 C7A 0.79(19) . . . . ? C2 N1 C7A C7 -177.28(13) . . . . ? C2 N1 C7A C3A 0.60(13) . . . . ? C6 C7 C7A N1 177.28(12) . . . . ? C6 C7 C7A C3A -0.36(18) . . . . ? N3 C3A C7A N1 -0.59(13) . . . . ? C4 C3A C7A N1 -179.08(11) . . . . ? N3 C3A C7A C7 177.55(11) . . . . ? C4 C3A C7A C7 -0.94(19) . . . . ? N3 C2 C8 C9 47.14(18) . . . . ? N1 C2 C8 C9 -127.20(13) . . . . ? N3 C2 C8 C8 -139.78(15) . . . 3_655 ? N1 C2 C8 C8 45.9(2) . . . 3_655 ? C8 C8 C9 C10 -3.5(2) 3_655 . . . ? C2 C8 C9 C10 169.67(12) . . . . ? C8 C9 C10 C10 -2.0(3) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.23 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.04