#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013906.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_2013906 loop_ _publ_author_name 'Lyakhov, Alexander S.' 'Voitekhovich, Sergei V.' 'Gaponik, Pavel N.' 'Ivashkevich, Ludmila S.' _publ_section_title ; 1-Phenyl-5-(piperidinomethyl)-1H-tetrazole ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o293 _journal_page_last o294 _journal_paper_doi 10.1107/S0108270104005554 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C13 H17 N5' _chemical_formula_moiety 'C13 H17 N5' _chemical_formula_sum 'C13 H17 N5' _chemical_formula_weight 243.32 _chemical_name_systematic ; 1-Phenyl-5-(piperidinomethyl)-1H-tetrazole ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 96.142(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.7537(13) _cell_length_b 10.436(3) _cell_length_c 15.937(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.3 _cell_measurement_theta_min 12.4 _cell_volume 1282.2(5) _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) ; _computing_publication_material ; SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003) ; _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al, 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nicolet R3m four-circle diffractometer' _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 0.71073 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 4125 _diffrn_reflns_theta_full 30.07 _diffrn_reflns_theta_max 30.07 _diffrn_reflns_theta_min 2.34 _diffrn_standards_decay_% none _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.46 _refine_diff_density_max 0.168 _refine_diff_density_min -0.251 _refine_ls_extinction_coef 0.480(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 3746 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0421 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0879P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1082 _refine_ls_wR_factor_ref 0.1198 _reflns_number_gt 2759 _reflns_number_total 3746 _reflns_threshold_expression I>2\s(I) _cod_data_source_file av1171.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2013906 _cod_database_fobs_code 2013906 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' 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 0.33395(12) 0.14877(8) 0.53722(5) 0.0455(2) Uani d . 1 . . N N2 0.23195(15) 0.13018(10) 0.46377(6) 0.0598(3) Uani d . 1 . . N N3 0.33297(18) 0.13906(11) 0.40455(6) 0.0697(3) Uani d . 1 . . N N4 0.49897(16) 0.16229(10) 0.43672(6) 0.0632(3) Uani d . 1 . . N C5 0.49825(15) 0.16835(9) 0.51921(7) 0.0482(3) Uani d . 1 . . C C6 0.26254(13) 0.13607(9) 0.61587(6) 0.0433(2) Uani d . 1 . . C C7 0.14675(15) 0.03748(11) 0.62453(8) 0.0513(3) Uani d . 1 . . C H7 0.1197(17) -0.0218(14) 0.5794(8) 0.063(4) Uiso d . 1 . . H C8 0.07734(16) 0.02440(12) 0.70039(8) 0.0589(3) Uani d . 1 . . C H8 -0.006(2) -0.0446(16) 0.7068(9) 0.077(4) Uiso d . 1 . . H C9 0.12399(16) 0.10749(14) 0.76591(8) 0.0610(3) Uani d . 1 . . C H9 0.0770(19) 0.0923(15) 0.8186(9) 0.078(4) Uiso d . 1 . . H C10 0.23807(16) 0.20551(14) 0.75615(7) 0.0588(3) Uani d . 1 . . C H10 0.267(2) 0.2671(17) 0.8010(10) 0.086(5) Uiso d . 1 . . H C11 0.30840(14) 0.22187(11) 0.68054(7) 0.0502(3) Uani d . 1 . . C H11 0.3870(18) 0.2920(13) 0.6702(8) 0.060(3) Uiso d . 1 . . H C12 0.65236(15) 0.19014(11) 0.58159(7) 0.0508(3) Uani d . 1 . . C H12A 0.6346(16) 0.1446(12) 0.6349(8) 0.053(3) Uiso d . 1 . . H H12B 0.7549(18) 0.1512(13) 0.5579(8) 0.063(4) Uiso d . 1 . . H N13 0.68014(11) 0.32565(8) 0.60180(5) 0.0441(2) Uani d . 1 . . N C14 0.73631(16) 0.39423(11) 0.52936(7) 0.0519(3) Uani d . 1 . . C H14A 0.6458(19) 0.3857(13) 0.4823(8) 0.064(4) Uiso d . 1 . . H H14B 0.849(2) 0.3515(14) 0.5120(9) 0.070(4) Uiso d . 1 . . H C15 0.76814(18) 0.53468(12) 0.54975(9) 0.0615(3) Uani d . 1 . . C H15A 0.8020(19) 0.5799(15) 0.4980(10) 0.076(4) Uiso d . 1 . . H H15B 0.657(2) 0.5723(15) 0.5626(9) 0.071(4) Uiso d . 1 . . H C16 0.90389(17) 0.55095(14) 0.62460(9) 0.0633(3) Uani d . 1 . . C H16A 1.017(2) 0.5169(15) 0.6112(9) 0.075(4) Uiso d . 1 . . H H16B 0.916(2) 0.6458(16) 0.6392(11) 0.087(5) Uiso d . 1 . . H C17 0.85428(18) 0.47332(14) 0.69841(8) 0.0622(3) Uani d . 1 . . C H17A 0.952(2) 0.4698(15) 0.7459(9) 0.076(4) Uiso d . 1 . . H H17B 0.749(2) 0.5138(15) 0.7203(9) 0.074(4) Uiso d . 1 . . H C18 0.81532(16) 0.33599(13) 0.67374(8) 0.0558(3) Uani d . 1 . . C H18A 0.927(2) 0.2922(14) 0.6587(9) 0.073(4) Uiso d . 1 . . H H18B 0.7723(17) 0.2852(14) 0.7186(9) 0.067(4) 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 0.0559(5) 0.0387(4) 0.0416(4) -0.0051(4) 0.0036(4) -0.0012(3) N2 0.0790(7) 0.0532(5) 0.0451(5) -0.0160(5) -0.0034(5) -0.0049(4) N3 0.1051(9) 0.0591(6) 0.0450(5) -0.0183(6) 0.0086(5) -0.0077(4) N4 0.0893(8) 0.0526(6) 0.0506(5) -0.0091(5) 0.0208(5) -0.0066(4) C5 0.0622(6) 0.0353(5) 0.0492(5) -0.0007(4) 0.0150(5) 0.0003(4) C6 0.0446(5) 0.0417(5) 0.0434(5) 0.0028(4) 0.0036(4) 0.0014(4) C7 0.0528(6) 0.0427(5) 0.0589(6) -0.0021(4) 0.0085(5) -0.0009(5) C8 0.0524(6) 0.0566(7) 0.0698(7) 0.0006(5) 0.0163(5) 0.0103(6) C9 0.0528(6) 0.0796(9) 0.0519(6) 0.0087(6) 0.0115(5) 0.0098(6) C10 0.0528(6) 0.0760(8) 0.0468(6) 0.0031(6) 0.0019(5) -0.0080(5) C11 0.0477(5) 0.0533(6) 0.0491(6) -0.0027(5) 0.0023(4) -0.0052(4) C12 0.0505(6) 0.0444(5) 0.0588(6) 0.0049(4) 0.0115(5) 0.0085(5) N13 0.0395(4) 0.0463(5) 0.0469(4) 0.0018(3) 0.0073(3) 0.0066(3) C14 0.0538(6) 0.0542(6) 0.0475(6) -0.0066(5) 0.0043(5) 0.0086(4) C15 0.0617(7) 0.0532(6) 0.0679(7) -0.0081(5) -0.0010(6) 0.0115(6) C16 0.0524(7) 0.0644(8) 0.0723(8) -0.0101(6) 0.0033(6) -0.0018(6) C17 0.0549(7) 0.0765(9) 0.0549(7) -0.0032(6) 0.0045(5) -0.0068(6) C18 0.0522(6) 0.0669(7) 0.0477(6) 0.0028(5) 0.0023(5) 0.0097(5) 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 C5 N1 N2 108.35(9) C5 N1 C6 131.51(9) N2 N1 C6 119.95(9) N3 N2 N1 106.10(10) N2 N3 N4 111.21(9) C5 N4 N3 106.32(10) N4 C5 N1 108.03(11) N4 C5 C12 125.84(11) N1 C5 C12 126.11(10) C7 C6 C11 121.71(11) C7 C6 N1 118.24(10) C11 C6 N1 120.05(9) C8 C7 C6 118.62(11) C8 C7 H7 121.4(8) C6 C7 H7 120.0(8) C9 C8 C7 120.43(12) C9 C8 H8 120.4(9) C7 C8 H8 119.1(9) C10 C9 C8 120.28(11) C10 C9 H9 122.0(9) C8 C9 H9 117.6(10) C9 C10 C11 120.60(12) C9 C10 H10 120.9(10) C11 C10 H10 118.5(10) C6 C11 C10 118.35(11) C6 C11 H11 118.4(7) C10 C11 H11 123.3(7) N13 C12 C5 112.59(9) N13 C12 H12A 107.7(7) C5 C12 H12A 108.8(7) N13 C12 H12B 111.8(8) C5 C12 H12B 107.4(8) H12A C12 H12B 108.4(11) C12 N13 C14 110.40(9) C12 N13 C18 108.57(9) C14 N13 C18 109.35(9) N13 C14 C15 111.04(10) N13 C14 H14A 108.2(8) C15 C14 H14A 109.9(8) N13 C14 H14B 109.2(8) C15 C14 H14B 110.3(8) H14A C14 H14B 108.1(11) C16 C15 C14 111.17(11) C16 C15 H15A 111.8(9) C14 C15 H15A 109.1(9) C16 C15 H15B 109.9(9) C14 C15 H15B 107.6(9) H15A C15 H15B 107.0(12) C17 C16 C15 109.86(11) C17 C16 H16A 106.3(9) C15 C16 H16A 110.3(9) C17 C16 H16B 111.6(9) C15 C16 H16B 109.3(10) H16A C16 H16B 109.4(13) C18 C17 C16 111.53(11) C18 C17 H17A 105.9(9) C16 C17 H17A 111.7(8) C18 C17 H17B 109.9(9) C16 C17 H17B 109.1(9) H17A C17 H17B 108.7(11) N13 C18 C17 112.25(10) N13 C18 H18A 109.4(8) C17 C18 H18A 109.4(8) N13 C18 H18B 105.0(8) C17 C18 H18B 113.6(8) H18A C18 H18B 106.9(12) 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 . 1.3510(15) yes N1 N2 . 1.3546(12) yes N1 C6 . 1.4296(13) yes N2 N3 . 1.2928(15) yes N3 N4 . 1.3553(17) yes N4 C5 . 1.3169(14) yes C5 C12 . 1.4878(16) yes C6 C7 . 1.3821(15) ? C6 C11 . 1.3828(15) ? C7 C8 . 1.3816(17) ? C7 H7 . 0.955(14) ? C8 C9 . 1.3757(19) ? C8 H8 . 0.981(16) ? C9 C10 . 1.372(2) ? C9 H9 . 0.963(15) ? C10 C11 . 1.3853(16) ? C10 H10 . 0.970(17) ? C11 H11 . 0.978(14) ? C12 N13 . 1.4613(15) yes C12 H12A . 0.996(13) ? C12 H12B . 1.002(14) ? N13 C14 . 1.4637(13) yes N13 C18 . 1.4724(14) yes C14 C15 . 1.5158(18) yes C14 H14A . 0.975(14) ? C14 H14B . 1.045(15) ? C15 C16 . 1.5136(19) yes C15 H15A . 1.010(15) ? C15 H15B . 0.987(15) ? C16 C17 . 1.5116(19) yes C16 H16A . 0.989(16) ? C16 H16B . 1.019(17) ? C17 C18 . 1.508(2) yes C17 H17A . 1.012(16) ? C17 H17B . 1.013(15) ? C18 H18A . 1.028(16) ? C18 H18B . 0.976(14) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C11 H11 N13 0.978(14) 2.648(13) 3.4395(15) 138.3(10) 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 -0.24(12) C6 N1 N2 N3 -175.69(9) N1 N2 N3 N4 0.33(13) N2 N3 N4 C5 -0.30(13) N3 N4 C5 N1 0.14(12) N3 N4 C5 C12 178.92(10) N2 N1 C5 N4 0.06(11) C6 N1 C5 N4 174.80(10) N2 N1 C5 C12 -178.73(9) C6 N1 C5 C12 -3.99(17) C5 N1 C6 C7 -133.92(11) N2 N1 C6 C7 40.32(13) C5 N1 C6 C11 46.70(15) N2 N1 C6 C11 -139.06(10) C11 C6 C7 C8 -0.73(17) N1 C6 C7 C8 179.90(10) C6 C7 C8 C9 -0.48(18) C7 C8 C9 C10 0.99(19) C8 C9 C10 C11 -0.31(19) C7 C6 C11 C10 1.39(17) N1 C6 C11 C10 -179.25(10) C9 C10 C11 C6 -0.86(18) N4 C5 C12 N13 91.94(13) N1 C5 C12 N13 -89.49(12) C5 C12 N13 C14 -69.67(11) C5 C12 N13 C18 170.48(9) C12 N13 C14 C15 -179.20(9) C18 N13 C14 C15 -59.81(12) N13 C14 C15 C16 58.41(14) C14 C15 C16 C17 -53.38(16) C15 C16 C17 C18 51.90(15) C12 N13 C18 C17 179.29(10) C14 N13 C18 C17 58.77(13) C16 C17 C18 N13 -55.59(14)