# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Mingwen Zhu' _publ_contact_author_email zhumingwen2001@yahoo.co.jp _publ_author_name 'Ryohei Yamaguchi' #============================================================================== data__shu32 _database_code_depnum_ccdc_archive 'CCDC 842301' #TrackingRef '- shu32.CIF' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H14 N4 ' _chemical_formula_moiety 'C16 H14 N4 ' _chemical_formula_weight 262.31 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 6.3969(14) _cell_length_b 5.7315(11) _cell_length_c 17.007(3) _cell_angle_alpha 90.0000 _cell_angle_beta 94.706(6) _cell_angle_gamma 90.0000 _cell_volume 621.4(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3261 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 173.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour unknown _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276.00 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.441 _exptl_absorpt_correction_T_max 0.978 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 5718 _diffrn_reflns_av_R_equivalents 0.070 _diffrn_reflns_theta_max 27.44 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_ambient_temperature 173.1 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 2.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1414 _reflns_number_gt 685 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.0905 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 691 _refine_ls_number_parameters 98 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0043Fo^2^ + 1.0000\s(Fo^2^)]' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.34 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 N(1) N 0.8004(4) 0.2259(5) 0.98144(17) 0.0396(9) Uani 1.00 1 d . . . N(2) N 1.0946(4) 0.1828(5) 0.91865(17) 0.0384(9) Uani 1.00 1 d . . . C(3) C 0.8082(5) 0.3988(6) 0.9248(2) 0.0372(11) Uani 1.00 1 d . . . C(4) C 0.9908(5) 0.3744(6) 0.8853(2) 0.0368(10) Uani 1.00 1 d . . . C(5) C 0.9715(5) 0.1011(6) 0.9757(2) 0.0350(10) Uani 1.00 1 d . . . C(6) C 1.2945(5) 0.0940(7) 0.8954(2) 0.0442(12) Uani 1.00 1 d . . . C(7) C 0.8994(6) 0.7021(7) 0.8057(2) 0.0434(11) Uani 1.00 1 d . . . C(8) C 0.7166(6) 0.7300(7) 0.8450(2) 0.0458(12) Uani 1.00 1 d . . . C(9) C 1.0405(6) 0.5251(7) 0.8252(2) 0.0422(12) Uani 1.00 1 d . . . C(10) C 0.6688(5) 0.5808(7) 0.9048(2) 0.0419(11) Uani 1.00 1 d . . . H(1) H 0.9266 0.8072 0.7646 0.052 Uiso 1.00 1 c R . . H(2) H 0.6237 0.8546 0.8301 0.055 Uiso 1.00 1 c R . . H(3) H 1.1653 0.5072 0.7992 0.051 Uiso 1.00 1 c R . . H(4) H 0.5450 0.6014 0.9313 0.050 Uiso 1.00 1 c R . . H(5) H 1.2678 -0.0195 0.8551 0.054 Uiso 1.00 1 c R . . H(6) H 1.3706 0.0243 0.9396 0.054 Uiso 1.00 1 c R . . H(7) H 1.3744 0.2181 0.8761 0.054 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N(1) 0.0218(18) 0.047(2) 0.0496(18) -0.0002(17) -0.0003(13) -0.0019(16) N(2) 0.0192(16) 0.048(2) 0.0486(17) -0.0003(15) 0.0029(14) -0.0011(16) C(3) 0.024(2) 0.044(2) 0.043(2) -0.0006(19) 0.0009(16) -0.0008(19) C(4) 0.025(2) 0.041(2) 0.043(2) 0.0009(19) -0.0029(16) -0.0040(18) C(5) 0.017(2) 0.042(2) 0.045(2) -0.0033(19) 0.0003(16) -0.0072(17) C(6) 0.025(2) 0.056(2) 0.053(2) 0.002(2) 0.0085(17) 0.004(2) C(7) 0.037(2) 0.048(2) 0.044(2) -0.001(2) -0.0009(18) 0.0046(19) C(8) 0.033(2) 0.051(2) 0.052(2) 0.009(2) -0.0036(19) -0.000(2) C(9) 0.028(2) 0.052(2) 0.047(2) -0.002(2) 0.0018(17) -0.004(2) C(10) 0.026(2) 0.050(2) 0.050(2) 0.004(2) 0.0004(17) 0.0027(19) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N(1) C(3) 1.385(4) yes . . N(1) C(5) 1.318(4) yes . . N(2) C(4) 1.381(4) yes . . N(2) C(5) 1.381(4) yes . . N(2) C(6) 1.461(4) yes . . C(3) C(4) 1.401(5) yes . . C(3) C(10) 1.396(5) yes . . C(4) C(9) 1.394(5) yes . . C(5) C(5) 1.452(5) yes . 3_757 C(7) C(8) 1.403(5) yes . . C(7) C(9) 1.380(5) yes . . C(8) C(10) 1.382(5) yes . . C(6) H(5) 0.950 no . . C(6) H(6) 0.950 no . . C(6) H(7) 0.950 no . . C(7) H(1) 0.950(5) no . . C(8) H(2) 0.950(5) no . . C(9) H(3) 0.950(5) no . . C(10) H(4) 0.950(5) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(3) N(1) C(5) 105.0(3) yes . . . C(4) N(2) C(5) 106.0(3) yes . . . C(4) N(2) C(6) 124.6(3) yes . . . C(5) N(2) C(6) 129.4(3) yes . . . N(1) C(3) C(4) 109.9(3) yes . . . N(1) C(3) C(10) 130.2(3) yes . . . C(4) C(3) C(10) 119.9(3) yes . . . N(2) C(4) C(3) 105.9(3) yes . . . N(2) C(4) C(9) 131.5(3) yes . . . C(3) C(4) C(9) 122.6(3) yes . . . N(1) C(5) N(2) 113.1(3) yes . . . N(1) C(5) C(5) 124.2(3) yes . . 3_757 N(2) C(5) C(5) 122.7(3) yes . . 3_757 C(8) C(7) C(9) 121.6(3) yes . . . C(7) C(8) C(10) 121.6(3) yes . . . C(4) C(9) C(7) 116.6(3) yes . . . C(3) C(10) C(8) 117.8(3) yes . . . N(2) C(6) H(5) 108.9 no . . . N(2) C(6) H(6) 109.6 no . . . N(2) C(6) H(7) 109.9 no . . . H(5) C(6) H(6) 109.5 no . . . H(5) C(6) H(7) 109.5 no . . . H(6) C(6) H(7) 109.5 no . . . C(8) C(7) H(1) 119.2(4) no . . . C(9) C(7) H(1) 119.2(4) no . . . C(7) C(8) H(2) 119.1(4) no . . . C(10) C(8) H(2) 119.3(4) no . . . C(4) C(9) H(3) 121.7(4) no . . . C(7) C(9) H(3) 121.7(4) no . . . C(3) C(10) H(4) 121.2(4) no . . . C(8) C(10) H(4) 121.0(4) no . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================