# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_shelxl _database_code_depnum_ccdc_archive 'CCDC 916246' #TrackingRef '16280_web_deposit_cif_file_0_KeikoORISAKU_1355824641.shelxl121211F.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_sum 'C24 H20 N4' _chemical_formula_moiety 'C24 H20 N4' _chemical_formula_weight 364.45 _chemical_melting_point ? 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 c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_Int_Tables_number 56 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 9.3776(5) _cell_length_b 13.9561(9) _cell_length_c 14.0544(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1839.37(19) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3104 _cell_measurement_theta_min 3.25 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.344 _exptl_crystal_size_mid 0.310 _exptl_crystal_size_min 0.185 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'NUMABS (Rigaku, 1999)' _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9854 _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15212 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2101 _reflns_number_gt 1765 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1281P)^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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2101 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1916 _refine_ls_wR_factor_gt 0.1763 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 0.53415(14) 0.46874(10) 0.35342(10) 0.0286(4) Uani 1 1 d . . . N2 N 0.38608(15) 0.59253(10) -0.05556(9) 0.0273(4) Uani 1 1 d . . . C1 C 0.63331(17) 0.47518(11) 0.28506(12) 0.0272(4) Uani 1 1 d . . . C2 C 0.67842(17) 0.56050(10) 0.24457(11) 0.0259(4) Uani 1 1 d . . . C3 C 0.61919(15) 0.64703(10) 0.27499(10) 0.0214(4) Uani 1 1 d . . . C4 C 0.51384(17) 0.64080(11) 0.34475(12) 0.0258(4) Uani 1 1 d . . . C5 C 0.47594(18) 0.55176(12) 0.38111(13) 0.0303(4) Uani 1 1 d . . . C6 C 0.66702(14) 0.74276(10) 0.23677(11) 0.0216(4) Uani 1 1 d . . . C7 C 0.66830(14) 0.75620(10) 0.12557(10) 0.0207(4) Uani 1 1 d . . . C8 C 0.33969(17) 0.64058(12) 0.02146(12) 0.0288(4) Uani 1 1 d . . . C9 C 0.42830(17) 0.69166(12) 0.08191(12) 0.0273(4) Uani 1 1 d . . . C10 C 0.57403(16) 0.69543(10) 0.06405(10) 0.0210(4) Uani 1 1 d . . . C11 C 0.62386(16) 0.64410(10) -0.01409(11) 0.0237(4) Uani 1 1 d . . . C12 C 0.52692(18) 0.59477(11) -0.07089(11) 0.0254(4) Uani 1 1 d . . . H1 H 0.6120(18) 0.7941(12) 0.2706(11) 0.022(4) Uiso 1 1 d . . . H2 H 0.6448(18) 0.8272(13) 0.1106(11) 0.022(4) Uiso 1 1 d . . . H3 H 0.6772(19) 0.4134(15) 0.2598(12) 0.037(5) Uiso 1 1 d . . . H4 H 0.403(3) 0.5461(15) 0.4362(15) 0.047(6) Uiso 1 1 d . . . H5 H 0.463(2) 0.6998(14) 0.3696(14) 0.034(5) Uiso 1 1 d . . . H6 H 0.720(2) 0.6410(14) -0.0272(13) 0.029(5) Uiso 1 1 d . . . H7 H 0.557(2) 0.5578(13) -0.1229(14) 0.027(5) Uiso 1 1 d . . . H8 H 0.390(2) 0.7252(15) 0.1338(14) 0.034(5) Uiso 1 1 d . . . H9 H 0.233(2) 0.6369(16) 0.0355(15) 0.045(5) Uiso 1 1 d . . . H10 H 0.752(2) 0.5597(13) 0.1944(14) 0.035(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 0.0269(7) 0.0292(7) 0.0296(8) 0.0033(6) -0.0002(5) -0.0056(5) N2 0.0252(7) 0.0283(7) 0.0284(7) -0.0003(5) -0.0015(5) -0.0019(5) C1 0.0256(8) 0.0262(8) 0.0299(9) -0.0007(7) -0.0005(6) -0.0018(6) C2 0.0245(8) 0.0263(8) 0.0269(8) 0.0002(6) 0.0042(6) 0.0004(6) C3 0.0190(7) 0.0245(8) 0.0207(8) -0.0006(5) -0.0019(5) -0.0021(5) C4 0.0220(8) 0.0266(8) 0.0289(8) -0.0034(6) 0.0027(6) -0.0011(6) C5 0.0272(9) 0.0341(10) 0.0294(9) -0.0004(6) 0.0060(6) -0.0040(6) C6 0.0189(7) 0.0230(7) 0.0230(8) -0.0017(5) 0.0010(5) 0.0006(5) C7 0.0175(8) 0.0210(7) 0.0235(8) 0.0000(5) 0.0007(5) 0.0005(5) C8 0.0206(8) 0.0341(9) 0.0317(9) -0.0035(6) -0.0009(6) -0.0011(6) C9 0.0204(8) 0.0325(9) 0.0291(8) -0.0042(6) 0.0003(6) 0.0006(6) C10 0.0208(8) 0.0199(7) 0.0222(7) 0.0023(5) -0.0017(5) 0.0001(5) C11 0.0199(8) 0.0257(8) 0.0255(8) 0.0009(6) 0.0015(6) -0.0009(6) C12 0.0281(9) 0.0222(8) 0.0260(8) -0.0019(6) 0.0001(6) -0.0005(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 C5 1.339(2) . ? N1 C1 1.340(2) . ? N2 C12 1.339(2) . ? N2 C8 1.346(2) . ? C1 C2 1.386(2) . ? C1 H3 1.02(2) . ? C2 C3 1.396(2) . ? C2 H10 0.99(2) . ? C3 C4 1.395(2) . ? C3 C6 1.5082(19) . ? C4 C5 1.390(2) . ? C4 H5 1.01(2) . ? C5 H4 1.04(2) . ? C6 C6 1.569(3) 4_665 ? C6 C7 1.574(2) . ? C6 H1 1.003(17) . ? C7 C10 1.499(2) . ? C7 C7 1.542(3) 4_665 ? C7 H2 1.037(18) . ? C8 C9 1.386(2) . ? C8 H9 1.02(2) . ? C9 C10 1.390(2) . ? C9 H8 0.94(2) . ? C10 C11 1.392(2) . ? C11 C12 1.392(2) . ? C11 H6 0.918(19) . ? C12 H7 0.938(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C1 115.68(14) . . ? C12 N2 C8 115.90(13) . . ? N1 C1 C2 124.32(15) . . ? N1 C1 H3 118.3(11) . . ? C2 C1 H3 117.4(11) . . ? C1 C2 C3 119.73(15) . . ? C1 C2 H10 119.8(11) . . ? C3 C2 H10 120.5(11) . . ? C4 C3 C2 116.31(13) . . ? C4 C3 C6 121.08(13) . . ? C2 C3 C6 122.60(13) . . ? C5 C4 C3 119.69(14) . . ? C5 C4 H5 118.7(11) . . ? C3 C4 H5 121.6(11) . . ? N1 C5 C4 124.24(16) . . ? N1 C5 H4 114.9(11) . . ? C4 C5 H4 120.7(11) . . ? C3 C6 C6 114.14(14) . 4_665 ? C3 C6 C7 117.48(12) . . ? C6 C6 C7 88.69(7) 4_665 . ? C3 C6 H1 108.1(9) . . ? C6 C6 H1 114.7(9) 4_665 . ? C7 C6 H1 112.9(9) . . ? C10 C7 C7 121.49(13) . 4_665 ? C10 C7 C6 120.04(12) . . ? C7 C7 C6 89.67(7) 4_665 . ? C10 C7 H2 107.4(9) . . ? C7 C7 H2 108.6(9) 4_665 . ? C6 C7 H2 108.3(9) . . ? N2 C8 C9 123.76(15) . . ? N2 C8 H9 116.6(12) . . ? C9 C8 H9 119.6(12) . . ? C8 C9 C10 119.87(15) . . ? C8 C9 H8 120.4(12) . . ? C10 C9 H8 119.7(12) . . ? C9 C10 C11 116.93(13) . . ? C9 C10 C7 119.79(13) . . ? C11 C10 C7 123.23(13) . . ? C12 C11 C10 119.19(14) . . ? C12 C11 H6 120.1(12) . . ? C10 C11 H6 120.7(12) . . ? N2 C12 C11 124.31(14) . . ? N2 C12 H7 114.2(11) . . ? C11 C12 H7 121.4(12) . . ? 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 C5 N1 C1 C2 1.2(2) . . . . ? N1 C1 C2 C3 -0.0(3) . . . . ? C1 C2 C3 C4 -1.2(2) . . . . ? C1 C2 C3 C6 177.65(13) . . . . ? C2 C3 C4 C5 1.3(2) . . . . ? C6 C3 C4 C5 -177.55(14) . . . . ? C1 N1 C5 C4 -1.1(3) . . . . ? C3 C4 C5 N1 -0.2(3) . . . . ? C4 C3 C6 C6 129.72(13) . . . 4_665 ? C2 C3 C6 C6 -49.09(16) . . . 4_665 ? C4 C3 C6 C7 -128.46(14) . . . . ? C2 C3 C6 C7 52.73(19) . . . . ? C3 C6 C7 C10 23.93(19) . . . . ? C6 C6 C7 C10 140.62(14) 4_665 . . . ? C3 C6 C7 C7 -102.95(14) . . . 4_665 ? C6 C6 C7 C7 13.75(15) 4_665 . . 4_665 ? C12 N2 C8 C9 1.2(2) . . . . ? N2 C8 C9 C10 0.3(3) . . . . ? C8 C9 C10 C11 -1.8(2) . . . . ? C8 C9 C10 C7 175.79(14) . . . . ? C7 C7 C10 C9 164.43(13) 4_665 . . . ? C6 C7 C10 C9 54.16(19) . . . . ? C7 C7 C10 C11 -18.2(2) 4_665 . . . ? C6 C7 C10 C11 -128.44(15) . . . . ? C9 C10 C11 C12 1.8(2) . . . . ? C7 C10 C11 C12 -175.70(14) . . . . ? C8 N2 C12 C11 -1.2(2) . . . . ? C10 C11 C12 N2 -0.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.448 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.063