Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof P J Steel' _publ_contact_author_address ; Department of Chemistry University of Canterbury Christchurch 1 ; _publ_contact_author_email P.STEEL@CHEM.CANTERBURY.AC.NZ _publ_section_title ; Solid State Conformations of Symmetrical Aromatic Biheterocycles: an X-Ray Crystallographic Investigation ; loop_ _publ_author_name 'P. J. Steel' 'Christopher M. Fitchett' 'Chris Richardson' data_3cfla _database_code_depnum_ccdc_archive 'CCDC 253922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,3'-Biquinoline ; _chemical_name_common 3,3'-Biquinoline _chemical_melting_point ? _chemical_formula_moiety 'C18 H12 N2' _chemical_formula_sum 'C18 H12 N2' _chemical_formula_weight 256.30 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.964(6) _cell_length_b 6.265(4) _cell_length_c 11.241(8) _cell_angle_alpha 90.00 _cell_angle_beta 107.109(18) _cell_angle_gamma 90.00 _cell_volume 603.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7019 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Blessing Acta Cryst. 1995(A51) 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 6814 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1070 _reflns_number_gt 532 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0529P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.043(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1070 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0907 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.843 _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 1.0826(2) 0.3186(3) 0.71406(18) 0.0307(6) Uani 1 1 d . . . C2 C 1.0934(3) 0.1518(4) 0.6477(2) 0.0292(6) Uani 1 1 d . . . H2A H 1.1809 0.0609 0.6792 0.035 Uiso 1 1 calc R . . C3 C 0.9862(3) 0.0957(3) 0.5334(2) 0.0231(6) Uani 1 1 d . . . C4 C 0.8610(3) 0.2247(3) 0.4907(2) 0.0264(6) Uani 1 1 d . . . H4A H 0.7844 0.1923 0.4144 0.032 Uiso 1 1 calc R . . C4A C 0.8439(3) 0.4047(3) 0.5580(2) 0.0244(6) Uani 1 1 d . . . C5 C 0.7164(3) 0.5428(4) 0.5182(2) 0.0324(7) Uani 1 1 d . . . H5A H 0.6367 0.5141 0.4429 0.039 Uiso 1 1 calc R . . C6 C 0.7059(3) 0.7176(4) 0.5864(2) 0.0346(7) Uani 1 1 d . . . H6A H 0.6183 0.8098 0.5593 0.042 Uiso 1 1 calc R . . C7 C 0.8223(3) 0.7624(4) 0.6954(2) 0.0320(7) Uani 1 1 d . . . H7A H 0.8149 0.8868 0.7417 0.038 Uiso 1 1 calc R . . C8 C 0.9459(3) 0.6313(3) 0.7365(2) 0.0313(7) Uani 1 1 d . . . H8A H 1.0249 0.6631 0.8116 0.038 Uiso 1 1 calc R . . C8A C 0.9577(3) 0.4482(3) 0.6685(2) 0.0242(6) 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 N1 0.0306(13) 0.0264(12) 0.0324(14) -0.0043(11) 0.0053(11) 0.0022(10) C2 0.0293(15) 0.0247(14) 0.0306(16) -0.0055(12) 0.0045(12) 0.0026(12) C3 0.0234(13) 0.0199(13) 0.0249(15) 0.0025(10) 0.0056(12) -0.0022(11) C4 0.0309(15) 0.0190(13) 0.0269(15) -0.0019(11) 0.0049(12) -0.0019(12) C4A 0.0289(15) 0.0198(13) 0.0244(15) 0.0039(11) 0.0079(13) 0.0018(11) C5 0.0367(16) 0.0267(15) 0.0314(15) 0.0000(12) 0.0062(13) 0.0037(12) C6 0.0392(18) 0.0249(14) 0.0409(18) 0.0017(13) 0.0136(15) 0.0076(12) C7 0.0418(17) 0.0184(13) 0.0412(18) -0.0020(12) 0.0206(15) 0.0000(12) C8 0.0330(16) 0.0269(14) 0.0349(17) -0.0039(12) 0.0116(13) -0.0052(12) C8A 0.0280(14) 0.0185(13) 0.0275(15) -0.0011(12) 0.0101(12) -0.0023(12) _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 1.304(3) . ? N1 C8A 1.356(3) . ? C2 C3 1.404(3) . ? C2 H2A 0.9500 . ? C3 C4 1.351(3) . ? C3 C3 1.473(4) 3_756 ? C4 C4A 1.391(3) . ? C4 H4A 0.9500 . ? C4A C8A 1.383(3) . ? C4A C5 1.397(3) . ? C5 C6 1.356(3) . ? C5 H5A 0.9500 . ? C6 C7 1.384(3) . ? C6 H6A 0.9500 . ? C7 C8 1.347(3) . ? C7 H7A 0.9500 . ? C8 C8A 1.400(3) . ? C8 H8A 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 C2 N1 C8A 117.1(2) . . ? N1 C2 C3 125.3(2) . . ? N1 C2 H2A 117.3 . . ? C3 C2 H2A 117.3 . . ? C4 C3 C2 116.6(2) . . ? C4 C3 C3 123.5(3) . 3_756 ? C2 C3 C3 119.9(3) . 3_756 ? C3 C4 C4A 120.3(2) . . ? C3 C4 H4A 119.8 . . ? C4A C4 H4A 119.8 . . ? C8A C4A C4 118.5(2) . . ? C8A C4A C5 118.9(2) . . ? C4 C4A C5 122.6(2) . . ? C6 C5 C4A 120.3(2) . . ? C6 C5 H5A 119.8 . . ? C4A C5 H5A 119.8 . . ? C5 C6 C7 120.3(2) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7A 119.7 . . ? C6 C7 H7A 119.7 . . ? C7 C8 C8A 119.9(2) . . ? C7 C8 H8A 120.0 . . ? C8A C8 H8A 120.0 . . ? N1 C8A C4A 122.0(2) . . ? N1 C8A C8 118.1(2) . . ? C4A C8A C8 119.9(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8A N1 C2 C3 -0.2(3) . . . . ? N1 C2 C3 C4 -1.0(3) . . . . ? N1 C2 C3 C3 179.0(3) . . . 3_756 ? C2 C3 C4 C4A 0.9(3) . . . . ? C3 C3 C4 C4A -179.1(2) 3_756 . . . ? C3 C4 C4A C8A 0.3(3) . . . . ? C3 C4 C4A C5 -179.8(2) . . . . ? C8A C4A C5 C6 0.7(3) . . . . ? C4 C4A C5 C6 -179.2(2) . . . . ? C4A C5 C6 C7 0.8(4) . . . . ? C5 C6 C7 C8 -1.3(4) . . . . ? C6 C7 C8 C8A 0.2(3) . . . . ? C2 N1 C8A C4A 1.5(3) . . . . ? C2 N1 C8A C8 -178.3(2) . . . . ? C4 C4A C8A N1 -1.6(3) . . . . ? C5 C4A C8A N1 178.5(2) . . . . ? C4 C4A C8A C8 178.2(2) . . . . ? C5 C4A C8A C8 -1.7(3) . . . . ? C7 C8 C8A N1 -179.0(2) . . . . ? C7 C8 C8A C4A 1.2(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.193 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.053 data_3cfb _database_code_depnum_ccdc_archive 'CCDC 253923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-biquinazoline ; _chemical_name_common 7 _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 N4' _chemical_formula_sum 'C16 H10 N4' _chemical_formula_weight 258.28 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.557(4) _cell_length_b 6.330(3) _cell_length_c 11.841(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.689(6) _cell_angle_gamma 90.00 _cell_volume 614.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8905 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Blessing Acta Cryst. 1995(A51) 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 7439 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 26.46 _reflns_number_total 1253 _reflns_number_gt 891 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0504P)^2^+0.5109P] 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 1253 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1328 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.3653(2) 0.2185(3) 0.49656(14) 0.0267(4) Uani 1 1 d . . . C2 C 0.4923(2) 0.0938(3) 0.53720(17) 0.0250(5) Uani 1 1 d . . . N3 N 0.6148(2) 0.1149(3) 0.64163(15) 0.0290(4) Uani 1 1 d . . . C4 C 0.6046(2) 0.2788(3) 0.70696(18) 0.0289(5) Uani 1 1 d . . . H4 H 0.6866 0.2979 0.7798 0.035 Uiso 1 1 calc R . . C4A C 0.4764(2) 0.4289(3) 0.67351(18) 0.0256(5) Uani 1 1 d . . . C5 C 0.4649(3) 0.6104(3) 0.74050(19) 0.0318(5) Uani 1 1 d . . . H5 H 0.5458 0.6371 0.8130 0.038 Uiso 1 1 calc R . . C6 C 0.3376(3) 0.7472(3) 0.7008(2) 0.0352(6) Uani 1 1 d . . . H6 H 0.3300 0.8693 0.7456 0.042 Uiso 1 1 calc R . . C7 C 0.2163(3) 0.7070(4) 0.5927(2) 0.0358(6) Uani 1 1 d . . . H7 H 0.1278 0.8027 0.5664 0.043 Uiso 1 1 calc R . . C8 C 0.2242(3) 0.5338(3) 0.52586(19) 0.0319(5) Uani 1 1 d . . . H8 H 0.1420 0.5096 0.4538 0.038 Uiso 1 1 calc R . . C8A C 0.3558(2) 0.3905(3) 0.56464(17) 0.0261(5) 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 N1 0.0275(9) 0.0261(9) 0.0260(9) 0.0000(7) 0.0069(7) 0.0009(7) C2 0.0267(10) 0.0211(10) 0.0273(10) 0.0014(8) 0.0080(9) -0.0024(8) N3 0.0279(9) 0.0257(9) 0.0296(9) -0.0036(7) 0.0023(7) -0.0004(7) C4 0.0272(11) 0.0295(12) 0.0266(11) -0.0039(9) 0.0021(8) -0.0041(9) C4A 0.0270(10) 0.0231(10) 0.0291(10) -0.0003(9) 0.0120(8) -0.0041(8) C5 0.0345(11) 0.0292(11) 0.0347(12) -0.0062(9) 0.0148(10) -0.0074(9) C6 0.0423(13) 0.0256(11) 0.0446(14) -0.0069(10) 0.0233(11) -0.0037(10) C7 0.0383(13) 0.0276(11) 0.0449(13) 0.0032(10) 0.0174(11) 0.0084(9) C8 0.0326(11) 0.0312(12) 0.0308(11) 0.0011(10) 0.0071(9) 0.0051(9) C8A 0.0296(11) 0.0231(10) 0.0280(11) 0.0019(9) 0.0120(9) -0.0024(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.318(3) . ? N1 C8A 1.371(3) . ? C2 N3 1.379(2) . ? C2 C2 1.507(4) 3_656 ? N3 C4 1.312(3) . ? C4 C4A 1.419(3) . ? C4A C5 1.416(3) . ? C4A C8A 1.422(3) . ? C5 C6 1.365(3) . ? C6 C7 1.420(3) . ? C7 C8 1.366(3) . ? C8 C8A 1.416(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C8A 116.29(17) . . ? N1 C2 N3 127.17(18) . . ? N1 C2 C2 117.4(2) . 3_656 ? N3 C2 C2 115.4(2) . 3_656 ? C4 N3 C2 116.35(17) . . ? N3 C4 C4A 122.79(18) . . ? C5 C4A C4 124.01(19) . . ? C5 C4A C8A 119.88(19) . . ? C4 C4A C8A 116.10(18) . . ? C6 C5 C4A 119.9(2) . . ? C5 C6 C7 120.1(2) . . ? C8 C7 C6 121.4(2) . . ? C7 C8 C8A 119.6(2) . . ? N1 C8A C8 119.59(18) . . ? N1 C8A C4A 121.29(18) . . ? C8 C8A C4A 119.12(19) . . ? 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 C8A N1 C2 N3 1.4(3) . . . . ? C8A N1 C2 C2 -178.7(2) . . . 3_656 ? N1 C2 N3 C4 -0.9(3) . . . . ? C2 C2 N3 C4 179.1(2) 3_656 . . . ? C2 N3 C4 C4A -0.4(3) . . . . ? N3 C4 C4A C5 -178.1(2) . . . . ? N3 C4 C4A C8A 1.0(3) . . . . ? C4 C4A C5 C6 179.5(2) . . . . ? C8A C4A C5 C6 0.5(3) . . . . ? C4A C5 C6 C7 0.2(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 C8A 0.0(3) . . . . ? C2 N1 C8A C8 178.97(18) . . . . ? C2 N1 C8A C4A -0.7(3) . . . . ? C7 C8 C8A N1 -178.90(19) . . . . ? C7 C8 C8A C4A 0.7(3) . . . . ? C5 C4A C8A N1 178.64(18) . . . . ? C4 C4A C8A N1 -0.4(3) . . . . ? C5 C4A C8A C8 -1.0(3) . . . . ? C4 C4A C8A C8 179.94(19) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.202 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.046 data_3cfh _database_code_depnum_ccdc_archive 'CCDC 253924' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-biquinoxaline ; _chemical_name_common 8 _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 N4' _chemical_formula_sum 'C16 H10 N4' _chemical_formula_weight 258.28 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.779(3) _cell_length_b 5.350(3) _cell_length_c 18.906(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.466(7) _cell_angle_gamma 90.00 _cell_volume 584.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.468 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8245 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Blessing Acta Cryst. 1995(A51) 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 6979 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0113 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1190 _reflns_number_gt 954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0767P)^2^+0.0090P] 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 1190 _refine_ls_number_parameters 91 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.84058(15) 0.25480(15) 0.53601(4) 0.0254(3) Uani 1 1 d . . . C2 C 1.00933(17) 0.09151(18) 0.52921(5) 0.0254(3) Uani 1 1 d . . . C3 C 1.20459(18) 0.0887(2) 0.57644(6) 0.0306(3) Uani 1 1 d . . . H3 H 1.3239 -0.0292 0.5683 0.037 Uiso 1 1 calc R . . N4 N 1.22886(15) 0.24032(16) 0.63070(5) 0.0305(3) Uani 1 1 d . . . C4A C 1.05441(17) 0.40968(18) 0.63930(5) 0.0252(3) Uani 1 1 d . . . C5 C 1.06737(17) 0.57931(19) 0.69635(5) 0.0283(3) Uani 1 1 d . . . H5 H 1.1952 0.5732 0.7289 0.034 Uiso 1 1 calc R . . C6 C 0.89688(19) 0.75202(19) 0.70486(5) 0.0295(3) Uani 1 1 d . . . H6 H 0.9061 0.8651 0.7436 0.035 Uiso 1 1 calc R . . C7 C 0.70691(17) 0.7641(2) 0.65664(6) 0.0296(3) Uani 1 1 d . . . H7 H 0.5903 0.8869 0.6628 0.036 Uiso 1 1 calc R . . C8 C 0.68906(17) 0.60098(19) 0.60122(5) 0.0281(3) Uani 1 1 d . . . H8 H 0.5601 0.6103 0.5692 0.034 Uiso 1 1 calc R . . C8A C 0.86142(17) 0.41882(18) 0.59145(5) 0.0243(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 N1 0.0269(5) 0.0264(5) 0.0230(5) 0.0017(3) -0.0001(4) 0.0015(3) C2 0.0273(5) 0.0264(6) 0.0224(6) 0.0035(4) 0.0016(4) 0.0002(4) C3 0.0308(6) 0.0323(6) 0.0284(6) -0.0025(5) -0.0034(4) 0.0063(4) N4 0.0300(5) 0.0327(5) 0.0286(5) -0.0016(4) -0.0041(4) 0.0040(4) C4A 0.0251(5) 0.0267(6) 0.0237(5) 0.0027(4) 0.0011(4) -0.0010(4) C5 0.0287(6) 0.0318(6) 0.0244(5) 0.0003(4) -0.0026(4) -0.0028(4) C6 0.0328(6) 0.0293(6) 0.0264(6) -0.0040(4) 0.0019(4) -0.0029(4) C7 0.0288(6) 0.0304(6) 0.0298(6) -0.0004(4) 0.0023(4) 0.0029(4) C8 0.0268(5) 0.0311(6) 0.0264(5) 0.0013(4) -0.0014(4) 0.0027(4) C8A 0.0266(5) 0.0248(6) 0.0214(5) 0.0028(4) 0.0011(4) -0.0026(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3179(14) . ? N1 C8A 1.3699(14) . ? C2 C3 1.4211(15) . ? C2 C2 1.478(2) 3_756 ? C3 N4 1.3125(14) . ? N4 C4A 1.3682(14) . ? C4A C5 1.4100(15) . ? C4A C8A 1.4188(15) . ? C5 C6 1.3632(15) . ? C6 C7 1.4105(15) . ? C7 C8 1.3656(15) . ? C8 C8A 1.4090(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C8A 116.64(10) . . ? N1 C2 C3 121.56(10) . . ? N1 C2 C2 118.17(12) . 3_756 ? C3 C2 C2 120.28(11) . 3_756 ? N4 C3 C2 123.49(10) . . ? C3 N4 C4A 115.96(9) . . ? N4 C4A C5 119.49(10) . . ? N4 C4A C8A 121.10(10) . . ? C5 C4A C8A 119.41(9) . . ? C6 C5 C4A 120.14(10) . . ? C5 C6 C7 120.52(10) . . ? C8 C7 C6 120.58(10) . . ? C7 C8 C8A 120.19(10) . . ? N1 C8A C8 119.65(10) . . ? N1 C8A C4A 121.20(9) . . ? C8 C8A C4A 119.15(10) . . ? 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 C8A N1 C2 C3 -0.94(15) . . . . ? C8A N1 C2 C2 178.88(10) . . . 3_756 ? N1 C2 C3 N4 2.05(17) . . . . ? C2 C2 C3 N4 -177.77(10) 3_756 . . . ? C2 C3 N4 C4A -1.21(16) . . . . ? C3 N4 C4A C5 180.00(9) . . . . ? C3 N4 C4A C8A -0.49(15) . . . . ? N4 C4A C5 C6 178.83(9) . . . . ? C8A C4A C5 C6 -0.69(15) . . . . ? C4A C5 C6 C7 -0.40(15) . . . . ? C5 C6 C7 C8 0.89(15) . . . . ? C6 C7 C8 C8A -0.26(15) . . . . ? C2 N1 C8A C8 179.01(8) . . . . ? C2 N1 C8A C4A -0.72(14) . . . . ? C7 C8 C8A N1 179.44(9) . . . . ? C7 C8 C8A C4A -0.82(15) . . . . ? N4 C4A C8A N1 1.52(15) . . . . ? C5 C4A C8A N1 -178.97(8) . . . . ? N4 C4A C8A C8 -178.22(9) . . . . ? C5 C4A C8A C8 1.29(14) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.174 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.045 data_3pjs2 _database_code_depnum_ccdc_archive 'CCDC 253925' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-Biquinazoline ; _chemical_name_common 4,4'-Biquinazoline _chemical_melting_point ? _chemical_formula_moiety 'C16 H10 N4' _chemical_formula_sum 'C16 H10 N4' _chemical_formula_weight 258.28 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 C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 22.523(17) _cell_length_b 3.912(3) _cell_length_c 6.979(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.140(10) _cell_angle_gamma 90.00 _cell_volume 590.6(7) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.630 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Blessing Acta Cryst. 1995(A51) 33-38' _exptl_special_details ; 4,4'-Biquinazoline ; _diffrn_ambient_temperature 163(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 3477 _diffrn_reflns_av_R_equivalents 0.0819 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.20 _reflns_number_total 619 _reflns_number_gt 466 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0683P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.031(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -2(6) _refine_ls_number_reflns 619 _refine_ls_number_parameters 92 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1045 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.964 _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 0.37021(12) 0.3323(8) 0.6872(4) 0.0297(9) Uani 1 1 d . . . C2 C 0.42687(15) 0.4280(10) 0.7823(5) 0.0298(9) Uani 1 1 d . . . H2 H 0.4325 0.5199 0.9122 0.036 Uiso 1 1 calc R . . N3 N 0.47831(11) 0.4107(7) 0.7165(4) 0.0266(8) Uani 1 1 d . . . C4 C 0.47160(14) 0.2821(8) 0.5366(5) 0.0209(8) Uani 1 1 d . . . C4A C 0.41301(14) 0.1584(8) 0.4165(5) 0.0206(8) Uani 1 1 d . . . C5 C 0.40235(15) 0.0013(8) 0.2265(5) 0.0257(9) Uani 1 1 d . . . H5 H 0.4357 -0.0276 0.1694 0.031 Uiso 1 1 calc R . . C6 C 0.34436(14) -0.1092(9) 0.1245(5) 0.0276(9) Uani 1 1 d . . . H6 H 0.3375 -0.2103 -0.0036 0.033 Uiso 1 1 calc R . . C7 C 0.29450(15) -0.0719(9) 0.2108(5) 0.0297(9) Uani 1 1 d . . . H7 H 0.2545 -0.1508 0.1402 0.036 Uiso 1 1 calc R . . C8 C 0.30331(15) 0.0752(10) 0.3933(5) 0.0289(9) Uani 1 1 d . . . H8 H 0.2694 0.0997 0.4485 0.035 Uiso 1 1 calc R . . C8A C 0.36243(14) 0.1915(9) 0.5011(5) 0.0236(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0360(17) 0.0187(19) 0.0366(18) -0.0004(15) 0.0137(14) 0.0006(15) C2 0.039(2) 0.017(2) 0.035(2) 0.0000(17) 0.0137(16) 0.0024(18) N3 0.0324(16) 0.0165(18) 0.0320(16) -0.0004(15) 0.0106(13) 0.0004(15) C4 0.0277(18) 0.0064(18) 0.0271(19) 0.0036(15) 0.0052(14) 0.0026(16) C4A 0.0253(17) 0.0083(19) 0.0268(18) 0.0041(16) 0.0048(15) 0.0014(15) C5 0.0320(19) 0.013(2) 0.0328(19) 0.0017(16) 0.0109(15) 0.0019(15) C6 0.0310(18) 0.015(2) 0.034(2) 0.0005(17) 0.0030(15) 0.0024(17) C7 0.0304(18) 0.0113(19) 0.044(2) 0.0043(18) 0.0037(16) -0.0006(17) C8 0.033(2) 0.015(2) 0.041(2) 0.0016(17) 0.0136(17) 0.0034(16) C8A 0.0301(19) 0.0112(19) 0.0306(19) 0.0053(17) 0.0101(16) 0.0024(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 N1 C2 1.318(4) . ? N1 C8A 1.377(4) . ? C2 N3 1.362(4) . ? C2 H2 0.9500 . ? N3 C4 1.322(4) . ? C4 C4A 1.436(4) . ? C4 C4 1.503(6) 2_656 ? C4A C5 1.420(4) . ? C4A C8A 1.427(4) . ? C5 C6 1.372(4) . ? C5 H5 0.9500 . ? C6 C7 1.422(4) . ? C6 H6 0.9500 . ? C7 C8 1.361(5) . ? C7 H7 0.9500 . ? C8 C8A 1.410(4) . ? C8 H8 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 C2 N1 C8A 116.1(3) . . ? N1 C2 N3 127.7(3) . . ? N1 C2 H2 116.2 . . ? N3 C2 H2 116.2 . . ? C4 N3 C2 117.2(3) . . ? N3 C4 C4A 121.7(3) . . ? N3 C4 C4 116.1(3) . 2_656 ? C4A C4 C4 122.2(3) . 2_656 ? C5 C4A C8A 118.6(3) . . ? C5 C4A C4 125.4(3) . . ? C8A C4A C4 116.0(3) . . ? C6 C5 C4A 120.7(3) . . ? C6 C5 H5 119.7 . . ? C4A C5 H5 119.7 . . ? C5 C6 C7 119.9(3) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.9(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C8A 120.4(3) . . ? C7 C8 H8 119.8 . . ? C8A C8 H8 119.8 . . ? N1 C8A C8 119.1(3) . . ? N1 C8A C4A 121.3(3) . . ? C8 C8A C4A 119.6(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 C8A N1 C2 N3 1.5(6) . . . . ? N1 C2 N3 C4 -0.3(6) . . . . ? C2 N3 C4 C4A -1.3(5) . . . . ? C2 N3 C4 C4 177.1(2) . . . 2_656 ? N3 C4 C4A C5 -176.7(3) . . . . ? C4 C4 C4A C5 5.0(4) 2_656 . . . ? N3 C4 C4A C8A 1.6(4) . . . . ? C4 C4 C4A C8A -176.68(19) 2_656 . . . ? C8A C4A C5 C6 1.5(5) . . . . ? C4 C4A C5 C6 179.7(3) . . . . ? C4A C5 C6 C7 -1.1(5) . . . . ? C5 C6 C7 C8 0.6(5) . . . . ? C6 C7 C8 C8A -0.5(5) . . . . ? C2 N1 C8A C8 178.3(3) . . . . ? C2 N1 C8A C4A -1.1(4) . . . . ? C7 C8 C8A N1 -178.6(3) . . . . ? C7 C8 C8A C4A 0.9(5) . . . . ? C5 C4A C8A N1 178.1(4) . . . . ? C4 C4A C8A N1 -0.3(4) . . . . ? C5 C4A C8A C8 -1.3(4) . . . . ? C4 C4A C8A C8 -179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.232 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.064 data_3cr4 _database_code_depnum_ccdc_archive 'CCDC 253926' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-Bibenzoxazole ; _chemical_name_common 2,2'-Bibenzoxazole _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 N2 O2' _chemical_formula_sum 'C14 H8 N2 O2' _chemical_formula_weight 236.22 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.6270(10) _cell_length_b 16.480(2) _cell_length_c 7.0040(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.340(10) _cell_angle_gamma 90.00 _cell_volume 532.54(15) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 5 _cell_measurement_theta_max 13 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.473 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details xscans _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(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 'Seimens P4s"' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 1733 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1044 _reflns_number_gt 741 _reflns_threshold_expression >2sigma(I) _computing_data_collection xscans _computing_cell_refinement xscans _computing_data_reduction xscans _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _computing_publication_material xcif _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^)+(0.0672P)^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 1044 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1126 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0973(3) 0.97964(8) 0.7604(2) 0.0307(4) Uani 1 1 d . . . C2 C 0.0980(4) 0.97369(11) 0.9530(3) 0.0286(5) Uani 1 1 d . . . N3 N 0.2740(3) 0.92070(9) 1.0361(3) 0.0283(4) Uani 1 1 d . . . C3A C 0.4071(4) 0.88640(11) 0.8830(3) 0.0266(5) Uani 1 1 d . . . C4 C 0.6177(4) 0.82559(12) 0.8804(3) 0.0324(5) Uani 1 1 d . . . H4 H 0.6958 0.8000 0.9944 0.039 Uiso 1 1 calc R . . C5 C 0.7055(4) 0.80495(12) 0.7032(3) 0.0348(6) Uani 1 1 d . . . H5 H 0.8462 0.7634 0.6951 0.042 Uiso 1 1 calc R . . C6 C 0.5956(4) 0.84276(12) 0.5356(3) 0.0343(5) Uani 1 1 d . . . H6 H 0.6662 0.8270 0.4172 0.041 Uiso 1 1 calc R . . C7A C 0.3004(4) 0.92227(11) 0.7144(3) 0.0270(5) Uani 1 1 d . . . C7 C 0.3854(4) 0.90304(12) 0.5363(3) 0.0309(5) Uani 1 1 d . . . H7 H 0.3070 0.9289 0.4227 0.037 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 O1 0.0251(7) 0.0268(7) 0.0403(10) 0.0003(6) 0.0032(6) 0.0053(6) C2 0.0224(9) 0.0245(9) 0.0393(13) -0.0008(9) 0.0059(8) -0.0019(8) N3 0.0225(8) 0.0257(8) 0.0370(11) 0.0013(7) 0.0028(7) 0.0013(7) C3A 0.0215(9) 0.0218(9) 0.0371(13) 0.0003(8) 0.0062(9) -0.0024(8) C4 0.0279(10) 0.0257(10) 0.0439(14) 0.0053(9) 0.0035(10) 0.0027(9) C5 0.0266(11) 0.0269(10) 0.0518(15) -0.0024(10) 0.0081(10) 0.0022(9) C6 0.0321(11) 0.0305(10) 0.0414(14) -0.0074(9) 0.0102(10) -0.0041(9) C7A 0.0193(9) 0.0216(9) 0.0404(13) -0.0007(9) 0.0033(8) -0.0005(8) C7 0.0286(10) 0.0305(10) 0.0337(13) -0.0014(9) 0.0023(9) -0.0021(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.352(3) . ? O1 C7A 1.388(2) . ? C2 N3 1.301(2) . ? C2 C2 1.449(4) 3_577 ? N3 C3A 1.396(3) . ? C3A C7A 1.378(3) . ? C3A C4 1.399(3) . ? C4 C5 1.378(3) . ? C5 C6 1.391(3) . ? C6 C7 1.391(3) . ? C7A C7 1.373(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C7A 103.40(15) . . ? N3 C2 O1 116.70(18) . . ? N3 C2 C2 126.2(3) . 3_577 ? O1 C2 C2 117.1(2) . 3_577 ? C2 N3 C3A 103.03(18) . . ? C7A C3A N3 109.54(16) . . ? C7A C3A C4 120.06(18) . . ? N3 C3A C4 130.41(19) . . ? C5 C4 C3A 116.2(2) . . ? C4 C5 C6 122.43(19) . . ? C7 C6 C5 121.9(2) . . ? C7 C7A C3A 124.80(18) . . ? C7 C7A O1 127.87(19) . . ? C3A C7A O1 107.33(17) . . ? C7A C7 C6 114.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7A O1 C2 N3 0.2(2) . . . . ? C7A O1 C2 C2 -179.3(2) . . . 3_577 ? O1 C2 N3 C3A -0.3(2) . . . . ? C2 C2 N3 C3A 179.2(2) 3_577 . . . ? C2 N3 C3A C7A 0.3(2) . . . . ? C2 N3 C3A C4 -179.93(19) . . . . ? C7A C3A C4 C5 -0.3(3) . . . . ? N3 C3A C4 C5 179.96(19) . . . . ? C3A C4 C5 C6 0.9(3) . . . . ? C4 C5 C6 C7 -1.2(3) . . . . ? N3 C3A C7A C7 179.76(18) . . . . ? C4 C3A C7A C7 0.0(3) . . . . ? N3 C3A C7A O1 -0.2(2) . . . . ? C4 C3A C7A O1 -179.98(16) . . . . ? C2 O1 C7A C7 -179.9(2) . . . . ? C2 O1 C7A C3A 0.00(18) . . . . ? C3A C7A C7 C6 -0.2(3) . . . . ? O1 C7A C7 C6 179.73(17) . . . . ? C5 C6 C7 C7A 0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.199 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.051 data_3cr8 _database_code_depnum_ccdc_archive 'CCDC 253927' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-Bibenzothiazole ; _chemical_name_common 2,2'-Bibenzothiazole _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 N2 S2' _chemical_formula_sum 'C14 H8 N2 S2' _chemical_formula_weight 268.34 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' S S 0.1246 0.1234 '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 8.9930(10) _cell_length_b 5.9880(10) _cell_length_c 11.445(2) _cell_angle_alpha 90.00 _cell_angle_beta 110.870(10) _cell_angle_gamma 90.00 _cell_volume 575.88(15) _cell_formula_units_Z 2 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 5 _cell_measurement_theta_max 12.5 _exptl_crystal_description block _exptl_crystal_colour red-green _exptl_crystal_size_max 0.77 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.441 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_T_max 0.945 _exptl_absorpt_process_details xscans _exptl_special_details ; ? ; _diffrn_ambient_temperature 168(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 'Seimens P4s' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1618 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 26.99 _reflns_number_total 1261 _reflns_number_gt 964 _reflns_threshold_expression >2sigma(I) _computing_data_collection xscans _computing_cell_refinement xscans _computing_data_reduction xscans _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics xp _computing_publication_material xcif _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^)+(0.0563P)^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 1261 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.928 _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 S1 S 0.57384(6) 0.18001(9) 0.17868(4) 0.02260(17) Uani 1 1 d . . . C2 C 0.5506(2) 0.0957(3) 0.02760(18) 0.0202(4) Uani 1 1 d . . . N3 N 0.6262(2) 0.2076(3) -0.03109(15) 0.0221(4) Uani 1 1 d . . . C3A C 0.7109(2) 0.3802(3) 0.04497(18) 0.0212(4) Uani 1 1 d . . . C4 C 0.8038(3) 0.5366(3) 0.0113(2) 0.0270(5) Uani 1 1 d . . . H4 H 0.8129 0.5310 -0.0688 0.032 Uiso 1 1 calc R . . C5 C 0.8816(2) 0.6987(4) 0.0962(2) 0.0289(5) Uani 1 1 d . . . H5 H 0.9453 0.8056 0.0743 0.035 Uiso 1 1 calc R . . C6 C 0.8683(2) 0.7083(3) 0.2144(2) 0.0277(5) Uani 1 1 d . . . H6 H 0.9234 0.8217 0.2714 0.033 Uiso 1 1 calc R . . C7 C 0.7769(2) 0.5565(3) 0.24942(19) 0.0243(4) Uani 1 1 d . . . H7 H 0.7682 0.5640 0.3296 0.029 Uiso 1 1 calc R . . C7A C 0.6972(2) 0.3910(3) 0.16361(18) 0.0204(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0252(3) 0.0236(3) 0.0208(3) -0.0036(2) 0.01036(19) -0.0047(2) C2 0.0217(9) 0.0198(9) 0.0181(9) 0.0000(8) 0.0060(8) 0.0030(8) N3 0.0254(8) 0.0210(8) 0.0193(8) 0.0000(6) 0.0075(7) -0.0008(7) C3A 0.0196(9) 0.0194(10) 0.0224(9) 0.0007(7) 0.0050(8) 0.0014(8) C4 0.0304(11) 0.0271(11) 0.0245(10) 0.0029(8) 0.0110(9) -0.0026(9) C5 0.0270(10) 0.0228(10) 0.0362(12) 0.0025(9) 0.0104(9) -0.0046(9) C6 0.0233(10) 0.0229(11) 0.0347(11) -0.0069(9) 0.0075(9) -0.0023(9) C7 0.0226(10) 0.0263(11) 0.0238(10) -0.0063(8) 0.0080(8) -0.0003(9) C7A 0.0183(9) 0.0183(9) 0.0239(9) 0.0005(8) 0.0069(8) 0.0033(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7A 1.730(2) . ? S1 C2 1.741(2) . ? C2 N3 1.300(3) . ? C2 C2 1.459(4) 3_655 ? N3 C3A 1.390(2) . ? C3A C4 1.397(3) . ? C3A C7A 1.408(3) . ? C4 C5 1.375(3) . ? C5 C6 1.401(3) . ? C6 C7 1.378(3) . ? C7 C7A 1.400(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7A S1 C2 88.12(9) . . ? N3 C2 C2 122.8(2) . 3_655 ? N3 C2 S1 117.63(15) . . ? C2 C2 S1 119.58(19) 3_655 . ? C2 N3 C3A 109.32(17) . . ? N3 C3A C4 124.99(18) . . ? N3 C3A C7A 114.92(17) . . ? C4 C3A C7A 120.09(18) . . ? C5 C4 C3A 118.9(2) . . ? C4 C5 C6 120.9(2) . . ? C7 C6 C5 121.29(19) . . ? C6 C7 C7A 118.18(19) . . ? C7 C7A C3A 120.70(19) . . ? C7 C7A S1 129.29(16) . . ? C3A C7A S1 110.01(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7A S1 C2 N3 0.55(16) . . . . ? C7A S1 C2 C2 -179.8(2) . . . 3_655 ? C2 C2 N3 C3A 179.5(2) 3_655 . . . ? S1 C2 N3 C3A -0.8(2) . . . . ? C2 N3 C3A C4 -178.87(19) . . . . ? C2 N3 C3A C7A 0.8(2) . . . . ? N3 C3A C4 C5 -179.90(19) . . . . ? C7A C3A C4 C5 0.5(3) . . . . ? C3A C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C7A 0.1(3) . . . . ? C6 C7 C7A C3A 0.2(3) . . . . ? C6 C7 C7A S1 -179.52(16) . . . . ? N3 C3A C7A C7 179.85(18) . . . . ? C4 C3A C7A C7 -0.5(3) . . . . ? N3 C3A C7A S1 -0.4(2) . . . . ? C4 C3A C7A S1 179.27(15) . . . . ? C2 S1 C7A C7 179.7(2) . . . . ? C2 S1 C7A C3A -0.07(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.430 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.070 data_3cr38pp _database_code_depnum_ccdc_archive 'CCDC 253928' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,1'-bibenzotriazole ; _chemical_name_common 1,1'-bibenzotriazole _chemical_melting_point 233-234 _chemical_formula_moiety 'C12 H8 N6' _chemical_formula_sum 'C12 H8 N6' _chemical_formula_weight 236.24 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 P2(1)2(1)2(1) 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' _cell_length_a 7.277(3) _cell_length_b 7.639(3) _cell_length_c 19.940(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1108.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; 1,1'-bibenzotriazole ; _diffrn_ambient_temperature 168(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 'SMART CCD (Siemens 1995)' _diffrn_measurement_method 'Exposures over 0.5\% \f or \w rotation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13016 _diffrn_reflns_av_R_equivalents 0.0978 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.05 _reflns_number_total 1170 _reflns_number_gt 929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens 1995)' _computing_cell_refinement 'SAINT (Siemens 1995)' _computing_data_reduction 'SAINT (Siemens 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.5840P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(7) _refine_ls_number_reflns 1170 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1233 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.146 _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 0.1431(5) 0.1162(5) 0.18170(17) 0.0319(10) Uani 1 1 d . . . N2 N -0.0335(5) 0.1078(6) 0.20526(19) 0.0387(11) Uani 1 1 d . . . N3 N -0.0247(5) 0.1252(6) 0.27023(18) 0.0377(11) Uani 1 1 d . . . C3A C 0.1567(6) 0.1458(6) 0.2900(2) 0.0258(10) Uani 1 1 d . . . C4 C 0.2319(6) 0.1711(6) 0.3536(2) 0.0269(10) Uani 1 1 d . . . H4 H 0.1566 0.1753 0.3925 0.032 Uiso 1 1 calc R . . C5 C 0.4177(7) 0.1893(6) 0.3576(2) 0.0322(12) Uani 1 1 d . . . H5 H 0.4736 0.2057 0.4002 0.039 Uiso 1 1 calc R . . C6 C 0.5301(6) 0.1842(6) 0.2990(2) 0.0337(12) Uani 1 1 d . . . H6 H 0.6591 0.1990 0.3036 0.040 Uiso 1 1 calc R . . C7 C 0.4576(6) 0.1585(6) 0.2358(2) 0.0302(11) Uani 1 1 d . . . H7 H 0.5326 0.1534 0.1968 0.036 Uiso 1 1 calc R . . C7A C 0.2678(6) 0.1407(6) 0.2328(2) 0.0261(10) Uani 1 1 d . . . N1' N 0.1774(5) 0.1029(5) 0.11452(16) 0.0274(9) Uani 1 1 d . . . N2' N 0.1855(6) -0.0606(5) 0.08391(17) 0.0339(10) Uani 1 1 d . . . N3' N 0.2027(6) -0.0354(5) 0.02004(18) 0.0307(10) Uani 1 1 d . . . C3A' C 0.2062(6) 0.1448(5) 0.0072(2) 0.0239(10) Uani 1 1 d . . . C4' C 0.2211(6) 0.2359(6) -0.0539(2) 0.0278(11) Uani 1 1 d . . . H4' H 0.2326 0.1767 -0.0956 0.033 Uiso 1 1 calc R . . C5' C 0.2181(6) 0.4158(6) -0.0498(2) 0.0313(11) Uani 1 1 d . . . H5' H 0.2283 0.4819 -0.0899 0.038 Uiso 1 1 calc R . . C6' C 0.2004(6) 0.5067(6) 0.0118(2) 0.0331(12) Uani 1 1 d . . . H6' H 0.1978 0.6310 0.0116 0.040 Uiso 1 1 calc R . . C7' C 0.1868(6) 0.4181(6) 0.0722(2) 0.0301(11) Uani 1 1 d . . . H7' H 0.1776 0.4772 0.1139 0.036 Uiso 1 1 calc R . . C7A' C 0.1876(6) 0.2345(5) 0.0674(2) 0.0218(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 N1 0.022(2) 0.047(3) 0.0269(19) -0.0029(18) 0.0035(16) -0.003(2) N2 0.019(2) 0.057(3) 0.041(2) -0.002(2) 0.0008(18) -0.004(2) N3 0.020(2) 0.061(3) 0.033(2) -0.004(2) 0.0016(18) -0.005(2) C3A 0.019(2) 0.029(2) 0.030(2) 0.002(2) 0.0018(19) -0.001(2) C4 0.020(2) 0.033(3) 0.027(2) -0.004(2) 0.0028(18) 0.001(2) C5 0.037(3) 0.031(3) 0.029(2) 0.000(2) -0.007(2) 0.000(2) C6 0.014(2) 0.039(3) 0.048(3) 0.000(3) -0.003(2) -0.002(2) C7 0.018(2) 0.035(3) 0.038(2) 0.000(3) 0.007(2) 0.000(2) C7A 0.024(2) 0.025(2) 0.028(2) -0.001(2) -0.0001(18) 0.000(2) N1' 0.033(2) 0.029(2) 0.0201(17) -0.0057(16) 0.0032(17) 0.002(2) N2' 0.046(3) 0.030(2) 0.026(2) 0.0012(17) 0.0014(19) 0.001(2) N3' 0.035(3) 0.026(2) 0.031(2) 0.0016(17) -0.0018(19) -0.001(2) C3A' 0.022(2) 0.017(2) 0.032(2) 0.0029(19) -0.0019(19) 0.000(2) C4' 0.027(3) 0.026(2) 0.030(2) -0.004(2) 0.001(2) 0.005(2) C5' 0.030(3) 0.027(3) 0.037(3) 0.008(2) 0.001(2) -0.002(2) C6' 0.027(3) 0.023(2) 0.049(3) 0.002(2) -0.003(2) 0.002(2) C7' 0.024(3) 0.028(2) 0.038(3) -0.015(2) 0.001(2) -0.004(2) C7A' 0.017(2) 0.023(2) 0.026(2) -0.0062(19) -0.002(2) 0.000(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N1' 1.366(5) . ? N1 N2 1.370(5) . ? N1 C7A 1.377(5) . ? N2 N3 1.304(5) . ? N3 C3A 1.386(5) . ? C3A C4 1.396(6) . ? C3A C7A 1.398(6) . ? C4 C5 1.362(7) . ? C4 H4 0.9500 . ? C5 C6 1.427(6) . ? C5 H5 0.9500 . ? C6 C7 1.381(6) . ? C6 H6 0.9500 . ? C7 C7A 1.389(6) . ? C7 H7 0.9500 . ? N1' C7A' 1.379(5) . ? N1' N2' 1.391(5) . ? N2' N3' 1.294(5) . ? N3' C3A' 1.400(5) . ? C3A' C7A' 1.387(6) . ? C3A' C4' 1.408(6) . ? C4' C5' 1.378(6) . ? C4' H4' 0.9500 . ? C5' C6' 1.415(6) . ? C5' H5' 0.9500 . ? C6' C7' 1.386(7) . ? C6' H6' 0.9500 . ? C7' C7A' 1.406(6) . ? C7' H7' 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 N1' N1 N2 120.3(3) . . ? N1' N1 C7A 128.0(4) . . ? N2 N1 C7A 111.7(3) . . ? N3 N2 N1 106.9(3) . . ? N2 N3 C3A 109.9(3) . . ? N3 C3A C4 130.3(4) . . ? N3 C3A C7A 108.4(4) . . ? C4 C3A C7A 121.2(4) . . ? C5 C4 C3A 117.2(4) . . ? C5 C4 H4 121.4 . . ? C3A C4 H4 121.4 . . ? C4 C5 C6 121.3(4) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 122.2(4) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C7A 115.6(4) . . ? C6 C7 H7 122.2 . . ? C7A C7 H7 122.2 . . ? N1 C7A C7 134.4(4) . . ? N1 C7A C3A 103.1(3) . . ? C7 C7A C3A 122.5(4) . . ? N1 N1' C7A' 128.6(4) . . ? N1 N1' N2' 120.3(3) . . ? C7A' N1' N2' 110.7(3) . . ? N3' N2' N1' 107.6(3) . . ? N2' N3' C3A' 109.1(3) . . ? C7A' C3A' N3' 109.0(4) . . ? C7A' C3A' C4' 120.8(4) . . ? N3' C3A' C4' 130.2(4) . . ? C5' C4' C3A' 116.1(4) . . ? C5' C4' H4' 122.0 . . ? C3A' C4' H4' 122.0 . . ? C4' C5' C6' 122.9(5) . . ? C4' C5' H5' 118.5 . . ? C6' C5' H5' 118.5 . . ? C7' C6' C5' 121.4(4) . . ? C7' C6' H6' 119.3 . . ? C5' C6' H6' 119.3 . . ? C6' C7' C7A' 115.3(4) . . ? C6' C7' H7' 122.3 . . ? C7A' C7' H7' 122.3 . . ? N1' C7A' C3A' 103.6(3) . . ? N1' C7A' C7' 132.9(4) . . ? C3A' C7A' C7' 123.5(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1' N1 N2 N3 -179.6(4) . . . . ? C7A N1 N2 N3 -0.4(6) . . . . ? N1 N2 N3 C3A 0.2(6) . . . . ? N2 N3 C3A C4 179.0(5) . . . . ? N2 N3 C3A C7A 0.0(6) . . . . ? N3 C3A C4 C5 -179.3(5) . . . . ? C7A C3A C4 C5 -0.4(7) . . . . ? C3A C4 C5 C6 0.5(8) . . . . ? C4 C5 C6 C7 -0.8(8) . . . . ? C5 C6 C7 C7A 1.0(7) . . . . ? N1' N1 C7A C7 -0.4(9) . . . . ? N2 N1 C7A C7 -179.5(6) . . . . ? N1' N1 C7A C3A 179.5(4) . . . . ? N2 N1 C7A C3A 0.4(5) . . . . ? C6 C7 C7A N1 179.0(5) . . . . ? C6 C7 C7A C3A -0.8(8) . . . . ? N3 C3A C7A N1 -0.2(5) . . . . ? C4 C3A C7A N1 -179.3(4) . . . . ? N3 C3A C7A C7 179.7(5) . . . . ? C4 C3A C7A C7 0.6(7) . . . . ? N2 N1 N1' C7A' 90.3(6) . . . . ? C7A N1 N1' C7A' -88.7(6) . . . . ? N2 N1 N1' N2' -81.8(6) . . . . ? C7A N1 N1' N2' 99.2(6) . . . . ? N1 N1' N2' N3' 174.3(4) . . . . ? C7A' N1' N2' N3' 0.9(5) . . . . ? N1' N2' N3' C3A' -0.1(6) . . . . ? N2' N3' C3A' C7A' -0.7(5) . . . . ? N2' N3' C3A' C4' -179.4(5) . . . . ? C7A' C3A' C4' C5' 0.7(6) . . . . ? N3' C3A' C4' C5' 179.2(5) . . . . ? C3A' C4' C5' C6' -0.2(7) . . . . ? C4' C5' C6' C7' 0.6(8) . . . . ? C5' C6' C7' C7A' -1.4(7) . . . . ? N1 N1' C7A' C3A' -174.0(4) . . . . ? N2' N1' C7A' C3A' -1.3(5) . . . . ? N1 N1' C7A' C7' 7.8(8) . . . . ? N2' N1' C7A' C7' -179.4(5) . . . . ? N3' C3A' C7A' N1' 1.2(5) . . . . ? C4' C3A' C7A' N1' 180.0(4) . . . . ? N3' C3A' C7A' C7' 179.6(5) . . . . ? C4' C3A' C7A' C7' -1.6(7) . . . . ? C6' C7' C7A' N1' 179.8(4) . . . . ? C6' C7' C7A' C3A' 1.9(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.206 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.056