# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address 'Changchun Institute of applied Chemistry, Chinese Academy of Science, 5625 Renmin Street, Changchun 130022, China' _publ_contact_author_address 'Changchun Institute of applied Chemistry, Chinese Academy of Science, 5625 Renmin Street, Changchun 130022, China' _publ_contact_author_email fshan@ciac.jl.cn #TrackingRef '7565_web_deposit_cif_file_0_YuLi_1318253218.V231.cif' _publ_contact_author_name 'Han Fushe' loop_ _publ_author_name 'Fushe Han' 'Yu Li' 'Lianxun Gao' data_v231 _database_code_depnum_ccdc_archive 'CCDC 848060' _audit_creation_method SHELXL-97 _chemical_name_systematic 5-Phenyl-2-p-tolyl-2H-tetrazole _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 N4' _chemical_melting_point ? _exptl_crystal_description block _exptl_crystal_colour 'color less' _diffrn_ambient_temperature 293(2) _chemical_formula_weight 236.28 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 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 11.0155(11) _cell_length_b 11.3718(11) _cell_length_c 9.8061(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.6242(18) _cell_angle_gamma 90.00 _cell_volume 1227.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1366 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 21.99 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9778 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD' _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 7119 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2160 _reflns_number_gt 1438 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0724P)^2^+0.0367P] 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 2160 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1191 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.78382(15) 0.15314(14) 0.09270(18) 0.0729(5) Uani 1 1 d . . . N2 N 0.87188(16) 0.12695(14) 0.01053(19) 0.0754(5) Uani 1 1 d . . . N3 N 0.90977(14) 0.22827(12) -0.04034(16) 0.0592(4) Uani 1 1 d . . . N4 N 0.84964(14) 0.32100(13) 0.00502(16) 0.0612(5) Uani 1 1 d . . . C1 C 0.67988(17) 0.33682(17) 0.16204(19) 0.0623(5) Uani 1 1 d . . . C2 C 0.6464(2) 0.4476(2) 0.1219(2) 0.0957(8) Uani 1 1 d . . . H2 H 0.6826 0.4822 0.0473 0.115 Uiso 1 1 calc R . . C3 C 0.5591(2) 0.5084(2) 0.1914(3) 0.1109(9) Uani 1 1 d . . . H3 H 0.5368 0.5836 0.1630 0.133 Uiso 1 1 calc R . . C4 C 0.5052(2) 0.4594(3) 0.3010(3) 0.0948(8) Uani 1 1 d . . . H4 H 0.4462 0.5005 0.3473 0.114 Uiso 1 1 calc R . . C5 C 0.5388(2) 0.3496(3) 0.3419(2) 0.0918(8) Uani 1 1 d . . . H5 H 0.5028 0.3159 0.4172 0.110 Uiso 1 1 calc R . . C6 C 0.62498(19) 0.2880(2) 0.2735(2) 0.0768(6) Uani 1 1 d . . . H6 H 0.6466 0.2127 0.3023 0.092 Uiso 1 1 calc R . . C7 C 0.77169(17) 0.27141(16) 0.08786(19) 0.0586(5) Uani 1 1 d . . . C8 C 1.00615(17) 0.23530(15) -0.13472(19) 0.0578(5) Uani 1 1 d . . . C9 C 1.03996(18) 0.34309(17) -0.1839(2) 0.0731(6) Uani 1 1 d . . . H9 H 1.0011 0.4112 -0.1558 0.088 Uiso 1 1 calc R . . C10 C 1.13271(19) 0.34888(18) -0.2759(2) 0.0776(6) Uani 1 1 d . . . H10 H 1.1561 0.4219 -0.3089 0.093 Uiso 1 1 calc R . . C11 C 1.19160(18) 0.24911(18) -0.3201(2) 0.0680(6) Uani 1 1 d . . . C12 C 1.15545(19) 0.14261(18) -0.2672(2) 0.0750(6) Uani 1 1 d . . . H12 H 1.1944 0.0743 -0.2944 0.090 Uiso 1 1 calc R . . C13 C 1.06388(19) 0.13447(17) -0.1758(2) 0.0706(6) Uani 1 1 d . . . H13 H 1.0410 0.0616 -0.1420 0.085 Uiso 1 1 calc R . . C14 C 1.2918(2) 0.2581(2) -0.4208(2) 0.0870(7) Uani 1 1 d . . . H14A H 1.3097 0.3394 -0.4374 0.130 Uiso 1 1 calc R . . H14B H 1.2665 0.2211 -0.5049 0.130 Uiso 1 1 calc R . . H14C H 1.3632 0.2196 -0.3845 0.130 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 0.0701(11) 0.0669(11) 0.0827(12) 0.0147(9) 0.0178(10) 0.0016(9) N2 0.0729(11) 0.0640(11) 0.0902(13) 0.0156(9) 0.0194(10) 0.0043(9) N3 0.0583(10) 0.0551(9) 0.0645(10) 0.0080(7) 0.0069(8) 0.0021(7) N4 0.0622(10) 0.0578(9) 0.0640(10) 0.0024(7) 0.0095(8) -0.0005(8) C1 0.0586(12) 0.0694(13) 0.0590(12) -0.0044(9) 0.0042(10) -0.0082(10) C2 0.112(2) 0.0760(15) 0.1020(19) 0.0069(13) 0.0462(16) 0.0131(13) C3 0.129(2) 0.0843(16) 0.122(2) -0.0034(15) 0.0484(19) 0.0211(15) C4 0.0818(17) 0.109(2) 0.0943(18) -0.0331(16) 0.0237(14) -0.0028(15) C5 0.0827(17) 0.119(2) 0.0755(16) -0.0051(15) 0.0252(14) -0.0103(15) C6 0.0697(14) 0.0915(16) 0.0700(14) 0.0050(11) 0.0126(12) -0.0060(12) C7 0.0555(11) 0.0643(12) 0.0562(11) 0.0037(9) 0.0035(9) -0.0049(9) C8 0.0543(11) 0.0633(12) 0.0558(11) 0.0051(9) 0.0027(9) 0.0030(9) C9 0.0740(14) 0.0668(13) 0.0795(14) 0.0158(11) 0.0207(12) 0.0128(10) C10 0.0764(14) 0.0758(14) 0.0815(15) 0.0252(12) 0.0180(12) 0.0078(11) C11 0.0599(13) 0.0876(15) 0.0565(12) 0.0020(10) 0.0017(10) 0.0086(11) C12 0.0762(15) 0.0723(13) 0.0773(14) -0.0128(11) 0.0135(12) 0.0034(11) C13 0.0762(14) 0.0598(12) 0.0764(14) -0.0044(10) 0.0134(12) -0.0017(10) C14 0.0724(15) 0.1207(19) 0.0687(15) 0.0034(13) 0.0167(12) 0.0080(13) _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 N2 1.313(2) . ? N1 C7 1.352(2) . ? N2 N3 1.3276(19) . ? N3 N4 1.3286(19) . ? N3 C8 1.430(2) . ? N4 C7 1.325(2) . ? C1 C2 1.368(3) . ? C1 C6 1.380(3) . ? C1 C7 1.465(2) . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.362(3) . ? C3 H3 0.9300 . ? C4 C5 1.360(3) . ? C4 H4 0.9300 . ? C5 C6 1.371(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.372(2) . ? C8 C13 1.377(2) . ? C9 C10 1.384(3) . ? C9 H9 0.9300 . ? C10 C11 1.383(3) . ? C10 H10 0.9300 . ? C11 C12 1.381(3) . ? C11 C14 1.506(3) . ? C12 C13 1.371(3) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? 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 N2 N1 C7 106.15(15) . . ? N1 N2 N3 106.22(15) . . ? N4 N3 N2 113.45(15) . . ? N4 N3 C8 123.95(14) . . ? N2 N3 C8 122.60(15) . . ? C7 N4 N3 101.85(14) . . ? C2 C1 C6 118.55(19) . . ? C2 C1 C7 120.61(17) . . ? C6 C1 C7 120.84(19) . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 119.2(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.7(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 120.5(2) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N4 C7 N1 112.32(16) . . ? N4 C7 C1 123.84(17) . . ? N1 C7 C1 123.81(16) . . ? C9 C8 C13 120.58(19) . . ? C9 C8 N3 119.40(16) . . ? C13 C8 N3 120.01(16) . . ? C8 C9 C10 118.96(18) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 121.80(19) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C12 C11 C10 117.34(19) . . ? C12 C11 C14 122.05(18) . . ? C10 C11 C14 120.60(18) . . ? C13 C12 C11 122.01(19) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C8 119.30(18) . . ? C12 C13 H13 120.4 . . ? C8 C13 H13 120.4 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.115 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.034