# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Fang Li' _publ_contact_author_email duzhiming430@sohu.com loop_ _publ_author_name 'Fang Li' 'Xiaomin Cong' 'Zhiming Du' 'Chunlin He' 'Linshuang Zhao' ; Lingqiao Meng ; data_bo1351 _database_code_depnum_ccdc_archive 'CCDC 868250' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H4 N12' _chemical_formula_weight 196.17 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 6.485(4) _cell_length_b 5.583(3) _cell_length_c 10.854(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.786(8) _cell_angle_gamma 90.00 _cell_volume 393.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1508 _cell_measurement_theta_min 3.638 _cell_measurement_theta_max 30.983 _exptl_crystal_description Block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 200 _exptl_absorpt_coefficient_mu 0.133 _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 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3937 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 31.01 _reflns_number_total 1244 _reflns_number_gt 1079 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0331P)^2^+0.2160P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment X,Y,Z,refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1244 _refine_ls_number_parameters 72 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 N6 N 0.53256(14) 0.04027(17) 0.05069(8) 0.0146(2) Uani 1 1 d . . . N3 N 0.35588(15) 0.54668(18) 0.20534(9) 0.0182(2) Uani 1 1 d . . . N4 N 0.48033(13) 0.35859(16) 0.19093(8) 0.01361(19) Uani 1 1 d . . . N5 N 0.63874(15) 0.29398(19) 0.27229(9) 0.0175(2) Uani 1 1 d . . . N1 N 0.26922(15) 0.35924(18) 0.03395(9) 0.0179(2) Uani 1 1 d . . . C1 C 0.42601(16) 0.24578(19) 0.08647(9) 0.0135(2) Uani 1 1 d . . . N2 N 0.22956(15) 0.54525(19) 0.11008(9) 0.0206(2) Uani 1 1 d . . . H5A H 0.582(3) 0.248(3) 0.3434(16) 0.032(4) Uiso 1 1 d . . . H5B H 0.716(3) 0.424(3) 0.2834(16) 0.040(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 N6 0.0164(4) 0.0148(4) 0.0124(4) -0.0014(3) -0.0022(3) 0.0007(3) N3 0.0188(4) 0.0171(4) 0.0186(4) -0.0028(4) -0.0007(3) 0.0038(3) N4 0.0142(4) 0.0139(4) 0.0127(4) -0.0014(3) -0.0020(3) 0.0002(3) N5 0.0165(4) 0.0207(5) 0.0152(4) -0.0013(4) -0.0068(3) -0.0007(4) N1 0.0185(4) 0.0189(5) 0.0163(4) -0.0013(3) -0.0033(3) 0.0049(4) C1 0.0145(4) 0.0143(5) 0.0116(4) -0.0003(4) -0.0015(3) 0.0001(4) N2 0.0216(5) 0.0204(5) 0.0197(5) -0.0024(4) -0.0034(4) 0.0056(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 N6 N6 1.2564(18) 3_655 ? N6 C1 1.3973(15) . ? N3 N2 1.3104(14) . ? N3 N4 1.3350(14) . ? N4 C1 1.3400(14) . ? N4 N5 1.3930(13) . ? N5 H5A 0.899(18) . ? N5 H5B 0.89(2) . ? N1 C1 1.3207(14) . ? N1 N2 1.3540(14) . ? 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 N6 N6 C1 112.07(11) 3_655 . ? N2 N3 N4 105.98(9) . . ? N3 N4 C1 108.45(9) . . ? N3 N4 N5 124.84(9) . . ? C1 N4 N5 126.71(10) . . ? N4 N5 H5A 108.1(11) . . ? N4 N5 H5B 106.5(12) . . ? H5A N5 H5B 110.9(16) . . ? C1 N1 N2 104.84(9) . . ? N1 C1 N4 109.37(10) . . ? N1 C1 N6 130.90(10) . . ? N4 C1 N6 119.73(9) . . ? N3 N2 N1 111.36(9) . . ? 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 N2 N3 N4 C1 -0.15(12) . . . . ? N2 N3 N4 N5 179.95(10) . . . . ? N2 N1 C1 N4 -0.05(12) . . . . ? N2 N1 C1 N6 179.54(11) . . . . ? N3 N4 C1 N1 0.13(12) . . . . ? N5 N4 C1 N1 -179.98(10) . . . . ? N3 N4 C1 N6 -179.52(9) . . . . ? N5 N4 C1 N6 0.38(16) . . . . ? N6 N6 C1 N1 2.37(19) 3_655 . . . ? N6 N6 C1 N4 -178.07(11) 3_655 . . . ? N4 N3 N2 N1 0.12(13) . . . . ? C1 N1 N2 N3 -0.04(13) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 31.01 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.289 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.068 # Attachment '- 2.cif' data_bo1125 _database_code_depnum_ccdc_archive 'CCDC 868251' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 N12' _chemical_formula_weight 276.30 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)/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 8.661(3) _cell_length_b 8.102(2) _cell_length_c 10.043(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.001(3) _cell_angle_gamma 90.00 _cell_volume 638.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 1953 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 29.12 _exptl_crystal_description Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.105 _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 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5340 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 29.10 _reflns_number_total 1683 _reflns_number_gt 1381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0531P)^2^+0.1630P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1683 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1006 _refine_ls_wR_factor_gt 0.0949 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.70483(12) 0.34639(13) 0.42140(11) 0.0239(2) Uani 1 1 d . . . N2 N 0.72697(13) 0.20750(13) 0.35765(11) 0.0271(2) Uani 1 1 d . . . N3 N 0.59814(12) 0.10506(13) 0.32574(11) 0.0255(2) Uani 1 1 d . . . N4 N 0.48977(11) 0.18051(12) 0.36845(10) 0.0197(2) Uani 1 1 d . . . N5 N 0.34804(12) 0.09634(13) 0.37075(11) 0.0232(2) Uani 1 1 d . . . N6 N 0.46379(11) 0.43112(12) 0.47865(10) 0.0204(2) Uani 1 1 d . . . C1 C 0.55611(13) 0.32765(14) 0.42756(11) 0.0189(2) Uani 1 1 d . . . C2 C 0.20759(14) 0.12428(14) 0.25804(12) 0.0209(2) Uani 1 1 d . . . C3 C 0.05658(16) 0.03561(17) 0.25789(15) 0.0305(3) Uani 1 1 d . . . H3A H 0.0921 -0.0334 0.3460 0.037 Uiso 1 1 calc R . . H3B H 0.0065 -0.0341 0.1702 0.037 Uiso 1 1 calc R . . H3C H -0.0281 0.1161 0.2574 0.037 Uiso 1 1 calc R . . C4 C 0.18457(14) 0.23398(15) 0.13152(13) 0.0263(3) Uani 1 1 d . . . H4A H 0.2216 0.3461 0.1674 0.032 Uiso 1 1 calc R . . H4B H 0.0641 0.2357 0.0620 0.032 Uiso 1 1 calc R . . H4C H 0.2529 0.1922 0.0821 0.032 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 0.0193(5) 0.0276(6) 0.0267(5) -0.0018(4) 0.0115(4) 0.0007(4) N2 0.0237(5) 0.0303(6) 0.0307(5) -0.0033(4) 0.0150(4) 0.0015(4) N3 0.0253(5) 0.0273(6) 0.0269(5) -0.0033(4) 0.0140(4) 0.0022(4) N4 0.0198(5) 0.0214(5) 0.0190(4) -0.0009(3) 0.0091(4) -0.0001(4) N5 0.0232(5) 0.0243(5) 0.0246(5) -0.0012(4) 0.0124(4) -0.0057(4) N6 0.0202(5) 0.0218(5) 0.0207(5) -0.0012(3) 0.0101(4) -0.0006(4) C1 0.0188(5) 0.0204(6) 0.0180(5) 0.0006(4) 0.0082(4) -0.0003(4) C2 0.0233(5) 0.0177(6) 0.0254(5) -0.0044(4) 0.0137(5) -0.0009(4) C3 0.0259(6) 0.0311(7) 0.0371(7) -0.0024(5) 0.0158(5) -0.0068(5) C4 0.0212(5) 0.0275(6) 0.0294(6) 0.0052(5) 0.0100(5) 0.0029(5) _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 C1 1.3241(15) . ? N1 N2 1.3479(14) . ? N2 N3 1.3169(14) . ? N3 N4 1.3337(13) . ? N4 C1 1.3474(15) . ? N4 N5 1.4129(13) . ? N5 C2 1.2839(15) . ? N6 N6 1.2631(19) 3_666 ? N6 C1 1.3971(14) . ? C2 C3 1.4916(16) . ? C2 C4 1.4933(16) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 105.25(9) . . ? N3 N2 N1 111.45(9) . . ? N2 N3 N4 105.78(10) . . ? N3 N4 C1 108.68(9) . . ? N3 N4 N5 121.23(10) . . ? C1 N4 N5 129.16(9) . . ? C2 N5 N4 113.98(9) . . ? N6 N6 C1 112.07(11) 3_666 . ? N1 C1 N4 108.84(10) . . ? N1 C1 N6 131.86(10) . . ? N4 C1 N6 119.27(9) . . ? N5 C2 C3 114.81(11) . . ? N5 C2 C4 126.24(10) . . ? C3 C2 C4 118.95(10) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 -0.36(12) . . . . ? N1 N2 N3 N4 0.68(13) . . . . ? N2 N3 N4 C1 -0.73(12) . . . . ? N2 N3 N4 N5 -170.58(9) . . . . ? N3 N4 N5 C2 -98.83(12) . . . . ? C1 N4 N5 C2 93.60(13) . . . . ? N2 N1 C1 N4 -0.11(12) . . . . ? N2 N1 C1 N6 -178.37(11) . . . . ? N3 N4 C1 N1 0.53(12) . . . . ? N5 N4 C1 N1 169.33(10) . . . . ? N3 N4 C1 N6 179.04(9) . . . . ? N5 N4 C1 N6 -12.16(16) . . . . ? N6 N6 C1 N1 2.76(19) 3_666 . . . ? N6 N6 C1 N4 -175.35(11) 3_666 . . . ? N4 N5 C2 C3 179.60(9) . . . . ? N4 N5 C2 C4 -0.15(16) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 29.10 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.249 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.044 # Attachment '- 3.cif.txt' data_bo1171 _database_code_depnum_ccdc_archive 'CCDC 876073' #TrackingRef '- 3.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H8 N6' _chemical_formula_weight 140.16 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 7.533(3) _cell_length_b 7.408(2) _cell_length_c 12.029(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.629(4) _cell_angle_gamma 90.00 _cell_volume 666.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2060 _cell_measurement_theta_min 2.722 _cell_measurement_theta_max 29.101 _exptl_crystal_description Chip _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.101 _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 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC10/Saturn724+ _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5681 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 29.13 _reflns_number_total 1768 _reflns_number_gt 1363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _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^)+(0.0251P)^2^+0.3060P] 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 1768 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0878 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.09268(15) 0.80172(15) 0.55523(9) 0.0223(3) Uani 1 1 d . . . N2 N 0.15237(16) 0.65284(16) 0.61546(9) 0.0238(3) Uani 1 1 d . . . N3 N 0.21745(16) 0.53219(16) 0.55473(9) 0.0228(3) Uani 1 1 d . . . N4 N 0.20051(14) 0.60339(15) 0.44801(9) 0.0186(2) Uani 1 1 d . . . N5 N 0.25203(15) 0.53503(15) 0.34926(9) 0.0211(2) Uani 1 1 d . . . N6 N 0.08645(19) 0.87443(18) 0.36194(10) 0.0298(3) Uani 1 1 d . . . C1 C 0.12307(17) 0.76765(17) 0.45031(11) 0.0196(3) Uani 1 1 d . . . C2 C 0.33227(17) 0.38261(18) 0.34756(11) 0.0215(3) Uani 1 1 d . . . C3 C 0.3804(2) 0.3288(2) 0.23514(12) 0.0315(4) Uani 1 1 d . . . H3A H 0.3416 0.4229 0.1804 0.038 Uiso 1 1 calc R . . H3B H 0.3211 0.2148 0.2123 0.038 Uiso 1 1 calc R . . H3C H 0.5102 0.3134 0.2390 0.038 Uiso 1 1 calc R . . C4 C 0.3806(2) 0.25415(19) 0.44202(12) 0.0281(3) Uani 1 1 d . . . H4A H 0.4437 0.3193 0.5056 0.034 Uiso 1 1 calc R . . H4B H 0.4582 0.1591 0.4179 0.034 Uiso 1 1 calc R . . H4C H 0.2716 0.1997 0.4645 0.034 Uiso 1 1 calc R . . H6A H 0.029(2) 0.977(2) 0.3731(14) 0.038(5) Uiso 1 1 d . . . H6B H 0.115(2) 0.842(2) 0.2950(15) 0.036(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 0.0281(6) 0.0234(6) 0.0160(5) -0.0018(4) 0.0046(4) 0.0019(5) N2 0.0300(6) 0.0240(6) 0.0179(5) -0.0011(4) 0.0053(5) 0.0010(5) N3 0.0304(6) 0.0241(6) 0.0144(5) 0.0014(4) 0.0053(4) 0.0002(5) N4 0.0230(6) 0.0197(5) 0.0136(5) -0.0012(4) 0.0042(4) 0.0004(4) N5 0.0262(6) 0.0229(6) 0.0151(5) -0.0034(4) 0.0056(4) 0.0010(5) N6 0.0483(8) 0.0264(7) 0.0158(6) 0.0007(5) 0.0083(5) 0.0148(6) C1 0.0218(6) 0.0201(6) 0.0172(6) -0.0034(5) 0.0035(5) -0.0007(5) C2 0.0204(6) 0.0230(7) 0.0215(7) -0.0042(5) 0.0038(5) -0.0019(6) C3 0.0368(8) 0.0335(8) 0.0249(7) -0.0085(6) 0.0069(6) 0.0073(7) C4 0.0330(8) 0.0229(7) 0.0293(8) 0.0000(6) 0.0070(6) 0.0058(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 C1 1.3325(16) . ? N1 N2 1.3668(16) . ? N2 N3 1.2867(16) . ? N3 N4 1.3801(15) . ? N4 C1 1.3511(17) . ? N4 N5 1.3873(14) . ? N5 C2 1.2820(17) . ? N6 C1 1.3283(18) . ? N6 H6A 0.894(18) . ? N6 H6B 0.892(18) . ? C2 C3 1.4942(19) . ? C2 C4 1.495(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 N2 105.50(11) . . ? N3 N2 N1 112.53(11) . . ? N2 N3 N4 105.20(11) . . ? C1 N4 N3 108.60(10) . . ? C1 N4 N5 120.70(11) . . ? N3 N4 N5 130.69(11) . . ? C2 N5 N4 120.94(11) . . ? C1 N6 H6A 116.5(11) . . ? C1 N6 H6B 120.7(11) . . ? H6A N6 H6B 122.7(15) . . ? N6 C1 N1 127.06(13) . . ? N6 C1 N4 124.77(12) . . ? N1 C1 N4 108.17(11) . . ? N5 C2 C3 114.43(12) . . ? N5 C2 C4 128.51(12) . . ? C3 C2 C4 117.06(12) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 N1 N2 N3 0.41(15) . . . . ? N1 N2 N3 N4 -0.08(15) . . . . ? N2 N3 N4 C1 -0.28(14) . . . . ? N2 N3 N4 N5 178.19(12) . . . . ? C1 N4 N5 C2 177.07(12) . . . . ? N3 N4 N5 C2 -1.2(2) . . . . ? N2 N1 C1 N6 179.94(14) . . . . ? N2 N1 C1 N4 -0.57(14) . . . . ? N3 N4 C1 N6 -179.95(13) . . . . ? N5 N4 C1 N6 1.4(2) . . . . ? N3 N4 C1 N1 0.54(14) . . . . ? N5 N4 C1 N1 -178.11(11) . . . . ? N4 N5 C2 C3 -179.42(12) . . . . ? N4 N5 C2 C4 1.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 29.13 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.263 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.043