#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013102.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2013102 loop_ _publ_author_name 'Lyakhov, Alexander S.' 'Voitekhovich, Sergei V.' 'Gaponik, Pavel N.' 'Ivashkevich, Ludmila S.' _publ_section_title ; Zwitterionic 5-(1-piperidiniomethyl)-1H-tetrazolide ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o22 _journal_page_last o23 _journal_paper_doi 10.1107/S0108270102020905 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C7 H13 N5' _chemical_formula_sum 'C7 H13 N5' _chemical_formula_weight 167.22 _chemical_name_systematic ; 1-(1-piperidiniomethyl)-1H-tetrazolide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.062(17) _cell_angle_beta 110.351(15) _cell_angle_gamma 93.176(16) _cell_formula_units_Z 2 _cell_length_a 6.1664(10) _cell_length_b 8.3913(18) _cell_length_c 8.6842(17) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.28 _cell_measurement_theta_min 20.40 _cell_volume 420.56(15) _computing_cell_refinement 'R3m Software' _computing_data_collection 'R3m Software (Nicolet, 1980)' _computing_data_reduction 'R3m Software' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Nicolet R3m four-circle' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_av_sigmaI/netI 0.017 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2761 _diffrn_reflns_theta_full 30.04 _diffrn_reflns_theta_max 30.04 _diffrn_reflns_theta_min 2.43 _diffrn_standards_decay_% 1.66 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 180 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.17 _refine_diff_density_min -0.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 161 _refine_ls_number_reflns 2467 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.045 _refine_ls_R_factor_gt 0.040 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.0378P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.112 _refine_ls_wR_factor_ref 0.118 _reflns_number_gt 2118 _reflns_number_total 2467 _reflns_threshold_expression I>2\s(I) _cod_data_source_file av1125.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 420.56(14) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2013102 _cod_database_fobs_code 2013102 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 -0.23825(15) 0.61929(11) 0.80123(10) 0.0448(2) Uani d . 1 . . N N2 -0.41908(15) 0.68757(11) 0.69104(11) 0.0479(2) Uani d . 1 . . N N3 -0.38644(14) 0.69921(10) 0.55060(10) 0.0438(2) Uani d . 1 . . N N4 -0.18145(13) 0.63976(9) 0.56555(9) 0.03756(19) Uani d . 1 . . N C5 -0.09640(14) 0.59166(10) 0.71974(9) 0.03267(18) Uani d . 1 . . C C6 0.12905(14) 0.51840(11) 0.79597(10) 0.03540(19) Uani d . 1 . . C H6A 0.252(2) 0.5757(14) 0.7671(15) 0.045(3) Uiso d . 1 . . H H6B 0.172(2) 0.5195(14) 0.9139(15) 0.039(3) Uiso d . 1 . . H N7 0.12534(11) 0.34779(9) 0.74078(8) 0.03126(17) Uani d . 1 . . N H7 0.120(2) 0.3488(16) 0.6309(17) 0.050(3) Uiso d . 1 . . H C8 0.35021(15) 0.27820(12) 0.83978(11) 0.0392(2) Uani d . 1 . . C H8A 0.363(2) 0.2864(14) 0.9580(15) 0.045(3) Uiso d . 1 . . H H8B 0.474(2) 0.3495(16) 0.8234(16) 0.051(3) Uiso d . 1 . . H C9 0.35742(17) 0.10701(13) 0.78682(13) 0.0464(2) Uani d . 1 . . C H9A 0.507(2) 0.0668(18) 0.8596(18) 0.062(4) Uiso d . 1 . . H H9B 0.363(2) 0.1039(15) 0.6761(16) 0.050(3) Uiso d . 1 . . H C10 0.1508(2) 0.00404(14) 0.79440(17) 0.0559(3) Uani d . 1 . . C H10A 0.162(3) -0.0057(19) 0.914(2) 0.068(4) Uiso d . 1 . . H H10B 0.150(3) -0.106(2) 0.758(2) 0.075(5) Uiso d . 1 . . H C11 -0.07294(18) 0.07791(13) 0.69544(15) 0.0495(2) Uani d . 1 . . C H11A -0.094(2) 0.0780(17) 0.5764(19) 0.058(4) Uiso d . 1 . . H H11B -0.208(3) 0.0136(19) 0.7034(19) 0.067(4) Uiso d . 1 . . H C12 -0.07836(14) 0.24810(11) 0.75148(12) 0.0377(2) Uani d . 1 . . C H12A -0.071(2) 0.2549(15) 0.8652(16) 0.045(3) Uiso d . 1 . . H H12B -0.216(2) 0.2989(14) 0.6819(15) 0.041(3) Uiso d . 1 . . H 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 N1 0.0507(5) 0.0569(5) 0.0382(4) 0.0096(4) 0.0290(4) 0.0065(3) N2 0.0469(4) 0.0559(5) 0.0523(5) 0.0098(4) 0.0306(4) 0.0087(4) N3 0.0402(4) 0.0527(5) 0.0424(4) 0.0060(3) 0.0189(3) 0.0074(3) N4 0.0381(4) 0.0491(4) 0.0300(3) 0.0030(3) 0.0174(3) 0.0039(3) C5 0.0365(4) 0.0378(4) 0.0284(3) -0.0021(3) 0.0180(3) -0.0001(3) C6 0.0340(4) 0.0430(4) 0.0298(4) -0.0030(3) 0.0127(3) -0.0015(3) N7 0.0283(3) 0.0436(4) 0.0241(3) 0.0011(3) 0.0121(2) 0.0016(2) C8 0.0285(4) 0.0571(5) 0.0324(4) 0.0046(3) 0.0107(3) 0.0056(3) C9 0.0413(5) 0.0565(6) 0.0460(5) 0.0150(4) 0.0192(4) 0.0118(4) C10 0.0563(6) 0.0474(6) 0.0697(7) 0.0086(5) 0.0284(6) 0.0137(5) C11 0.0430(5) 0.0452(5) 0.0607(6) -0.0031(4) 0.0196(5) -0.0053(4) C12 0.0299(4) 0.0449(4) 0.0408(4) -0.0020(3) 0.0162(3) -0.0006(3) 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' 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 C5 N1 N2 104.73(7) yes N3 N2 N1 109.69(8) yes N2 N3 N4 108.96(8) yes C5 N4 N3 105.17(7) yes N4 C5 N1 111.45(8) yes N4 C5 C6 125.48(7) yes N1 C5 C6 123.06(7) yes C5 C6 N7 113.13(7) ? C5 C6 H6A 111.2(7) ? N7 C6 H6A 105.7(7) ? C5 C6 H6B 110.0(7) ? N7 C6 H6B 107.5(7) ? H6A C6 H6B 109.1(10) ? C12 N7 C8 111.25(7) yes C12 N7 C6 112.71(7) yes C8 N7 C6 109.07(7) yes C12 N7 H7 109.4(8) yes C8 N7 H7 106.6(8) yes C6 N7 H7 107.6(8) yes N7 C8 C9 111.24(8) ? N7 C8 H8A 106.5(7) ? C9 C8 H8A 111.7(7) ? N7 C8 H8B 105.8(7) ? C9 C8 H8B 112.5(8) ? H8A C8 H8B 108.7(10) ? C8 C9 C10 111.64(9) ? C8 C9 H9A 107.3(9) ? C10 C9 H9A 111.7(9) ? C8 C9 H9B 109.9(8) ? C10 C9 H9B 110.3(8) ? H9A C9 H9B 105.9(11) ? C11 C10 C9 110.14(9) ? C11 C10 H10A 110.1(9) ? C9 C10 H10A 109.1(9) ? C11 C10 H10B 110.6(10) ? C9 C10 H10B 112.8(10) ? H10A C10 H10B 104.1(13) ? C12 C11 C10 111.69(9) ? C12 C11 H11A 108.4(8) ? C10 C11 H11A 110.9(8) ? C12 C11 H11B 109.6(9) ? C10 C11 H11B 110.5(9) ? H11A C11 H11B 105.6(12) ? N7 C12 C11 110.50(8) ? N7 C12 H12A 106.9(7) ? C11 C12 H12A 112.3(7) ? N7 C12 H12B 106.1(7) ? C11 C12 H12B 111.8(7) ? H12A C12 H12B 109.0(10) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 . 1.3313(11) yes N1 N2 . 1.3480(13) yes N2 N3 . 1.3062(12) yes N3 N4 . 1.3489(11) yes N4 C5 . 1.3293(11) yes C5 C6 . 1.4847(12) ? C6 N7 . 1.5058(12) yes C6 H6A . 0.979(13) ? C6 H6B . 0.965(12) ? N7 C12 . 1.5003(11) yes N7 C8 . 1.5048(11) yes N7 H7 . 0.943(14) ? C8 C9 . 1.5156(15) ? C8 H8A . 1.004(13) ? C8 H8B . 0.994(14) ? C9 C10 . 1.5203(16) ? C9 H9A . 0.995(15) ? C9 H9B . 0.975(14) ? C10 C11 . 1.5156(16) ? C10 H10A . 1.018(17) ? C10 H10B . 0.978(17) ? C11 C12 . 1.5141(14) ? C11 H11A . 0.996(15) ? C11 H11B . 0.988(16) ? C12 H12A . 0.974(13) ? C12 H12B . 0.975(12) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N7 H7 N4 2_566 0.943(14) 1.874(14) 2.8007(11) 166.9(11) C9 H9B N3 2_566 0.975(14) 2.608(13) 3.4067(15) 139.3(10) C6 H6A N2 1_655 0.979(13) 2.482(13) 3.4555(13) 172.9(10) C12 H12B N3 2_466 0.975(12) 2.579(12) 3.4801(14) 153.7(9) C8 H8A N1 2_567 1.004(13) 2.602(13) 3.5345(13) 154.5(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 C5 N1 N2 N3 0.27(11) N1 N2 N3 N4 -0.50(11) N2 N3 N4 C5 0.51(10) N3 N4 C5 N1 -0.35(10) N3 N4 C5 C6 -179.44(8) N2 N1 C5 N4 0.06(11) N2 N1 C5 C6 179.18(8) N4 C5 C6 N7 -74.86(10) N1 C5 C6 N7 106.15(9) C5 C6 N7 C12 -48.92(9) C5 C6 N7 C8 -173.00(6) C12 N7 C8 C9 56.12(9) C6 N7 C8 C9 -178.94(7) N7 C8 C9 C10 -55.01(11) C8 C9 C10 C11 54.36(13) C9 C10 C11 C12 -55.55(13) C8 N7 C12 C11 -56.86(10) C6 N7 C12 C11 -179.73(7) C10 C11 C12 N7 57.06(12)