# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? #TrackingRef '- revised_cif_3_6_1-H-Tetrazole,1-(Phenylmethyl).cif' _publ_contact_author 'Rex Palmer' _publ_contact_author_email rex.palmer@btinternet.com _publ_requested_category FM loop_ _publ_author_name 'John Spencer' 'Hiren Patel' 'John J. Deadman' 'Rex A. Palmer' 'Louise Male' 'Simon J. Coles' ; O.G.Uzoh ; 'Sarah L. Price' _publ_contact_author_name 'Rex Palmer' data_1-H-Tetrazole,1-(Phenylmethyl)_(2008src0576_CCDC804779) _database_code_depnum_ccdc_archive 'CCDC 804779' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-H-Tetrazole, 1-(Phenylmethyl) ; _chemical_name_common '1-H-Tetrazole, 1-(Phenylmethyl)' _chemical_melting_point 'not measured' _chemical_formula_moiety ; C8 H8 N4 ; _chemical_formula_sum 'C8 H8 N4' _chemical_formula_weight 160.18 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.6843(5) _cell_length_b 5.5794(4) _cell_length_c 9.4459(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.949(4) _cell_angle_gamma 90.00 _cell_volume 397.61(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5624 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 27.45 _exptl_crystal_description Shard _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 168 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9921 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details 'Sheldrick, G. M. SADABS 2007/2' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type BrukerNoniusRoperCCDcameraon\k-goniostat _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _diffrn_reflns_number 5629 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 27.45 _reflns_number_total 977 _reflns_number_gt 822 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELX-S (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'MERCURY (Bruno et al 2002)' _computing_publication_material SHELX97 _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. In the final refinement all symmetry equivalents and Friedel opposites were merged as the anomalous scattering effects were too small to produce meaningful indications of the absolute structure. ; _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^)+(0.0149P)^2^+0.0804P] 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 1718 _refine_ls_number_parameters 113 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0870 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 C7 C 0.3268(2) 0.0713(4) 0.1234(2) 0.0233(4) Uani 1 1 d . . . C8 C 0.3471(3) 0.2524(4) 0.0268(2) 0.0262(4) Uani 1 1 d . . . H8 H 0.4191 0.3873 0.0591 0.031 Uiso 1 1 calc R . . C9 C 0.2632(3) 0.2376(4) -0.1158(2) 0.0295(5) Uani 1 1 d . . . H9 H 0.2779 0.3620 -0.1812 0.035 Uiso 1 1 calc R . . C10 C 0.1576(3) 0.0415(4) -0.1637(2) 0.0314(5) Uani 1 1 d . . . H10 H 0.1001 0.0316 -0.2619 0.038 Uiso 1 1 calc R . . C11 C 0.1357(3) -0.1402(5) -0.0686(2) 0.0312(5) Uani 1 1 d . . . H11 H 0.0633 -0.2747 -0.1012 0.037 Uiso 1 1 calc R . . C12 C 0.2199(2) -0.1242(4) 0.0742(2) 0.0273(4) Uani 1 1 d . . . H12 H 0.2045 -0.2484 0.1395 0.033 Uiso 1 1 calc R . . C6 C 0.4204(3) 0.0846(4) 0.2787(2) 0.0278(5) Uani 1 1 d . . . H6A H 0.4326 -0.0791 0.3198 0.033 Uiso 1 1 calc R . . H6B H 0.5410 0.1503 0.2830 0.033 Uiso 1 1 calc R . . C5 C 0.1996(3) 0.1792(4) 0.4413(2) 0.0305(5) Uani 1 1 d . . . N1 N 0.3248(2) 0.2356(3) 0.36642(17) 0.0245(4) Uani 1 1 d . . . N2 N 0.3505(2) 0.4736(3) 0.3762(2) 0.0300(4) Uani 1 1 d . . . N3 N 0.2432(2) 0.5566(4) 0.45558(18) 0.0303(4) Uani 1 1 d . . . N4 N 0.1461(2) 0.3741(4) 0.49835(18) 0.0315(4) Uani 1 1 d . . . H5 H 0.162(3) 0.029(4) 0.453(2) 0.034(6) 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 C7 0.0224(9) 0.0248(10) 0.0234(10) -0.0002(9) 0.0064(8) 0.0036(9) C8 0.0252(10) 0.0249(10) 0.0297(12) -0.0003(9) 0.0085(9) -0.0008(9) C9 0.0332(11) 0.0283(11) 0.0291(12) 0.0049(9) 0.0115(9) 0.0010(10) C10 0.0298(11) 0.0404(13) 0.0228(11) -0.0017(10) 0.0020(9) 0.0029(10) C11 0.0272(10) 0.0280(10) 0.0368(12) -0.0026(11) 0.0019(9) -0.0011(10) C12 0.0279(10) 0.0237(10) 0.0315(11) 0.0028(11) 0.0090(9) 0.0001(10) C6 0.0276(11) 0.0272(11) 0.0290(12) -0.0005(9) 0.0059(9) 0.0028(9) C5 0.0370(13) 0.0272(12) 0.0293(13) 0.0021(10) 0.0115(10) -0.0027(10) N1 0.0296(9) 0.0239(9) 0.0192(9) -0.0009(8) 0.0025(7) -0.0004(8) N2 0.0331(10) 0.0228(9) 0.0334(11) -0.0012(8) 0.0051(9) -0.0023(7) N3 0.0351(10) 0.0282(9) 0.0261(9) 0.0006(8) 0.0025(8) 0.0032(8) N4 0.0348(9) 0.0297(9) 0.0302(10) -0.0006(9) 0.0068(8) 0.0004(9) _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 C7 C8 1.390(3) . ? C7 C12 1.392(3) . ? C7 C6 1.508(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9500 . ? C9 C10 1.386(3) . ? C9 H9 0.9500 . ? C10 C11 1.386(3) . ? C10 H10 0.9500 . ? C11 C12 1.383(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C6 N1 1.472(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C5 N4 1.314(3) . ? C5 N1 1.336(3) . ? C5 H5 0.90(2) . ? N1 N2 1.343(2) . ? N2 N3 1.301(2) . ? N3 N4 1.368(3) . ? 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 C8 C7 C12 118.89(18) . . ? C8 C7 C6 120.73(18) . . ? C12 C7 C6 120.38(18) . . ? C9 C8 C7 120.48(19) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.12(19) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 120.07(19) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C7 120.9(2) . . ? C11 C12 H12 119.6 . . ? C7 C12 H12 119.6 . . ? N1 C6 C7 112.26(16) . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? N4 C5 N1 109.6(2) . . ? N4 C5 H5 126.0(14) . . ? N1 C5 H5 124.4(14) . . ? C5 N1 N2 107.95(18) . . ? C5 N1 C6 130.53(18) . . ? N2 N1 C6 121.45(17) . . ? N3 N2 N1 106.89(17) . . ? N2 N3 N4 110.24(18) . . ? C5 N4 N3 105.34(15) . . ? 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 C12 C7 C8 C9 -0.4(3) . . . . ? C6 C7 C8 C9 179.02(18) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? C8 C7 C12 C11 0.4(3) . . . . ? C6 C7 C12 C11 -178.95(18) . . . . ? C8 C7 C6 N1 82.1(2) . . . . ? C12 C7 C6 N1 -98.6(2) . . . . ? N4 C5 N1 N2 -0.3(2) . . . . ? N4 C5 N1 C6 -177.20(18) . . . . ? C7 C6 N1 C5 89.9(3) . . . . ? C7 C6 N1 N2 -86.7(2) . . . . ? C5 N1 N2 N3 0.2(2) . . . . ? C6 N1 N2 N3 177.48(16) . . . . ? N1 N2 N3 N4 -0.1(2) . . . . ? N1 C5 N4 N3 0.2(2) . . . . ? N2 N3 N4 C5 -0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.191 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.042