# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_z _database_code_depnum_ccdc_archive 'CCDC 899934' #TrackingRef 'web_deposit_cif_file_0_NingJiao_1346742824.3aa.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 N2' _chemical_formula_weight 158.20 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 Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.5482(10) _cell_length_b 10.7471(12) _cell_length_c 9.6662(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 888.02(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9800 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9475 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_sigmaI/netI 0.0462 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1532 _reflns_number_gt 1335 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0690P)^2^+0.0945P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4(4) _refine_ls_number_reflns 1532 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.2226(2) 0.26385(17) 0.2921(2) 0.0447(5) Uani 1 1 d . . . H1A H 0.2712 0.2746 0.2151 0.054 Uiso 1 1 calc R . . N2 N 0.1662(2) 0.27952(19) 0.51547(19) 0.0505(5) Uani 1 1 d . . . C1 C 0.0538(3) 0.2042(2) 0.4508(2) 0.0441(6) Uani 1 1 d . . . C2 C -0.0767(3) 0.1443(3) 0.5062(3) 0.0612(7) Uani 1 1 d . . . H2A H -0.1030 0.1514 0.5992 0.073 Uiso 1 1 calc R . . C3 C -0.1648(3) 0.0738(2) 0.4153(3) 0.0661(8) Uani 1 1 d . . . H3A H -0.2516 0.0312 0.4489 0.079 Uiso 1 1 calc R . . C4 C -0.1287(3) 0.0643(2) 0.2779(3) 0.0604(7) Uani 1 1 d . . . H4A H -0.1922 0.0161 0.2210 0.072 Uiso 1 1 calc R . . C5 C -0.0016(3) 0.1239(2) 0.2212(3) 0.0534(6) Uani 1 1 d . . . H5A H 0.0230 0.1172 0.1278 0.064 Uiso 1 1 calc R . . C6 C 0.0886(2) 0.19502(18) 0.3123(2) 0.0400(5) Uani 1 1 d . . . C7 C 0.2630(3) 0.3112(2) 0.4164(2) 0.0471(5) Uani 1 1 d . . . C8 C 0.3998(3) 0.3920(3) 0.4367(3) 0.0669(8) Uani 1 1 d . . . H8A H 0.4047 0.4331 0.5272 0.080 Uiso 1 1 calc R . . C9 C 0.5524(4) 0.3607(5) 0.3767(6) 0.1227(18) Uani 1 1 d . . . H9A H 0.6450 0.3786 0.4312 0.147 Uiso 1 1 calc R . . H9B H 0.5592 0.2861 0.3204 0.147 Uiso 1 1 calc R . . C10 C 0.4658(5) 0.4644(4) 0.3221(5) 0.1109(15) Uani 1 1 d . . . H10A H 0.4183 0.4550 0.2316 0.133 Uiso 1 1 calc R . . H10B H 0.5041 0.5474 0.3424 0.133 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 0.0507(10) 0.0489(10) 0.0345(10) 0.0001(9) 0.0025(9) -0.0009(8) N2 0.0611(12) 0.0544(12) 0.0360(11) -0.0020(9) -0.0047(9) -0.0022(10) C1 0.0481(13) 0.0430(13) 0.0413(12) 0.0023(9) -0.0036(10) -0.0006(10) C2 0.0683(16) 0.0677(17) 0.0477(14) 0.0070(13) 0.0040(12) -0.0067(13) C3 0.0643(16) 0.0655(16) 0.0686(19) 0.0128(15) -0.0018(14) -0.0188(14) C4 0.0657(15) 0.0507(14) 0.0648(17) 0.0003(13) -0.0157(13) -0.0131(11) C5 0.0623(15) 0.0541(14) 0.0437(13) -0.0026(11) -0.0075(11) -0.0003(12) C6 0.0432(11) 0.0384(11) 0.0385(11) 0.0028(9) -0.0041(10) 0.0023(8) C7 0.0521(13) 0.0493(12) 0.0399(12) -0.0007(10) -0.0036(10) 0.0020(10) C8 0.0661(16) 0.0759(18) 0.0587(16) -0.0106(14) -0.0044(14) -0.0200(14) C9 0.064(2) 0.111(3) 0.193(5) -0.042(4) 0.014(3) -0.020(2) C10 0.129(3) 0.119(4) 0.085(2) 0.004(2) -0.002(2) -0.076(3) _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 C7 1.349(3) . ? N1 C6 1.378(3) . ? N1 H1A 0.8600 . ? N2 C7 1.310(3) . ? N2 C1 1.403(3) . ? C1 C6 1.375(3) . ? C1 C2 1.394(3) . ? C2 C3 1.383(4) . ? C2 H2A 0.9300 . ? C3 C4 1.367(5) . ? C3 H3A 0.9300 . ? C4 C5 1.375(4) . ? C4 H4A 0.9300 . ? C5 C6 1.398(3) . ? C5 H5A 0.9300 . ? C7 C8 1.470(4) . ? C8 C10 1.467(5) . ? C8 C9 1.467(5) . ? C8 H8A 0.9800 . ? C9 C10 1.439(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? 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 C7 N1 C6 106.8(2) . . ? C7 N1 H1A 126.6 . . ? C6 N1 H1A 126.6 . . ? C7 N2 C1 104.87(19) . . ? C6 C1 C2 120.9(2) . . ? C6 C1 N2 109.1(2) . . ? C2 C1 N2 130.0(2) . . ? C3 C2 C1 116.4(2) . . ? C3 C2 H2A 121.8 . . ? C1 C2 H2A 121.8 . . ? C4 C3 C2 122.3(2) . . ? C4 C3 H3A 118.8 . . ? C2 C3 H3A 118.8 . . ? C3 C4 C5 122.0(2) . . ? C3 C4 H4A 119.0 . . ? C5 C4 H4A 119.0 . . ? C4 C5 C6 116.1(2) . . ? C4 C5 H5A 122.0 . . ? C6 C5 H5A 122.0 . . ? C1 C6 N1 106.19(19) . . ? C1 C6 C5 122.2(2) . . ? N1 C6 C5 131.5(2) . . ? N2 C7 N1 113.0(2) . . ? N2 C7 C8 123.9(2) . . ? N1 C7 C8 123.1(2) . . ? C10 C8 C9 58.7(3) . . ? C10 C8 C7 121.2(3) . . ? C9 C8 C7 121.2(3) . . ? C10 C8 H8A 114.8 . . ? C9 C8 H8A 114.8 . . ? C7 C8 H8A 114.8 . . ? C10 C9 C8 60.6(2) . . ? C10 C9 H9A 117.7 . . ? C8 C9 H9A 117.7 . . ? C10 C9 H9B 117.7 . . ? C8 C9 H9B 117.7 . . ? H9A C9 H9B 114.8 . . ? C9 C10 C8 60.6(3) . . ? C9 C10 H10A 117.7 . . ? C8 C10 H10A 117.7 . . ? C9 C10 H10B 117.7 . . ? C8 C10 H10B 117.7 . . ? H10A C10 H10B 114.8 . . ? 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 C7 N2 C1 C6 -0.6(2) . . . . ? C7 N2 C1 C2 179.8(2) . . . . ? C6 C1 C2 C3 1.6(4) . . . . ? N2 C1 C2 C3 -178.8(2) . . . . ? C1 C2 C3 C4 -1.1(4) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? C2 C1 C6 N1 -179.9(2) . . . . ? N2 C1 C6 N1 0.4(2) . . . . ? C2 C1 C6 C5 -1.5(3) . . . . ? N2 C1 C6 C5 178.85(19) . . . . ? C7 N1 C6 C1 -0.1(2) . . . . ? C7 N1 C6 C5 -178.3(2) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C4 C5 C6 N1 178.7(2) . . . . ? C1 N2 C7 N1 0.5(3) . . . . ? C1 N2 C7 C8 179.3(2) . . . . ? C6 N1 C7 N2 -0.3(3) . . . . ? C6 N1 C7 C8 -179.1(2) . . . . ? N2 C7 C8 C10 -155.1(3) . . . . ? N1 C7 C8 C10 23.6(5) . . . . ? N2 C7 C8 C9 134.9(4) . . . . ? N1 C7 C8 C9 -46.4(5) . . . . ? C7 C8 C9 C10 109.9(3) . . . . ? C7 C8 C10 C9 -110.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.161 _refine_diff_density_min -0.139 _refine_diff_density_rms 0.036