#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/05/2010589.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_2010589 loop_ _publ_author_name 'Lyakhov, Alexander S.' 'Ivashkevich, Dmitri O.' 'Gaponik, Pavel N.' 'Grigoriev, Yuri V.' 'Ivashkevich, Ludmila S.' _publ_section_title ; 1-(2,4,6-Trimethylphenyl)-1H-1,2,3,4-tetrazole ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 256 _journal_page_last 257 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C10 H12 N4' _chemical_formula_sum 'C10 H12 N4' _chemical_formula_weight 188.24 _chemical_name_common 1-(2,4,6-trimethylphenyl)tetrazole _chemical_name_systematic ; 1-(2,4,6-trimethylphenyl)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' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 100.97(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.220(2) _cell_length_b 7.2950(10) _cell_length_c 17.470(4) _cell_measurement_reflns_used 22 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.87 _cell_measurement_theta_min 10.14 _cell_volume 1028.4(4) _computing_cell_refinement 'R3m Software' _computing_data_collection 'R3m Software (Nicolet, 19XX)' _computing_data_reduction 'R3m Software' _computing_molecular_graphics 'Ortep-III for Windows (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _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 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 .71069 _diffrn_reflns_av_R_equivalents .0229 _diffrn_reflns_av_sigmaI/netI .0305 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 2642 _diffrn_reflns_theta_full 27.56 _diffrn_reflns_theta_max 27.56 _diffrn_reflns_theta_min 2.37 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .078 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 400 _exptl_crystal_size_max .55 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .35 _refine_diff_density_max .266 _refine_diff_density_min -.206 _refine_ls_extinction_coef .074(9) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 2386 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all .0907 _refine_ls_R_factor_gt .0528 _refine_ls_shift/su_max .004 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.3158P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1901 _reflns_number_gt 1357 _reflns_number_total 2386 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file av1031.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_database_code 2010589 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 .9784(2) .8232(2) .16103(10) .0518(5) Uani d . 1 . . N N2 .9553(3) .6539(3) .12982(13) .0759(6) Uani d . 1 . . N N3 .8467(3) .5751(3) .16355(15) .0852(7) Uani d . 1 . . N N4 .7980(3) .6876(3) .21636(14) .0775(6) Uani d . 1 . . N C5 .8809(3) .8389(3) .21348(15) .0657(6) Uani d . 1 . . C C11 1.0873(2) .9539(3) .13535(11) .0481(5) Uani d . 1 . . C C12 1.0171(2) 1.1062(3) .09339(11) .0496(5) Uani d . 1 . . C C13 1.1251(3) 1.2309(3) .06940(13) .0580(5) Uani d . 1 . . C C14 1.2951(3) 1.2060(3) .08470(13) .0615(6) Uani d . 1 . . C C15 1.3587(3) 1.0532(3) .12724(14) .0611(6) Uani d . 1 . . C C16 1.2581(2) .9250(3) .15358(12) .0543(5) Uani d . 1 . . C C17 .8336(3) 1.1381(4) .07468(16) .0635(6) Uani d . 1 . . C C18 1.4069(4) 1.3416(5) .0555(2) .0887(9) Uani d . 1 . . C C19 1.3321(3) .7641(4) .20228(18) .0766(7) Uani d . 1 . . C H5 .875(3) .950(4) .2439(17) .093(9) Uiso d . 1 . . H H13 1.078(3) 1.334(3) .0417(14) .072(7) Uiso d . 1 . . H H15 1.474(3) 1.034(4) .1388(15) .077(7) Uiso d . 1 . . H H17A .767(4) 1.028(4) .0547(17) .094(9) Uiso d . 1 . . H H17B .809(4) 1.227(4) .0308(17) .090 Uiso d . 1 . . H H17C .790(3) 1.192(4) .1157(17) .090 Uiso d . 1 . . H H18A 1.348(4) 1.444(4) .0329(17) .090 Uiso d . 1 . . H H18B 1.435(3) 1.287(4) .0086(17) .090 Uiso d . 1 . . H H18C 1.502(4) 1.367(4) .0948(17) .090 Uiso d . 1 . . H H19A 1.296(3) .765(4) .2523(17) .090 Uiso d . 1 . . H H19B 1.448(4) .762(4) .2032(17) .090 Uiso d . 1 . . H H19C 1.303(4) .660(4) .1765(17) .090 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 .0498(9) .0442(9) .0642(10) -.0009(7) .0178(8) -.0037(7) N2 .0941(15) .0520(11) .0877(14) -.0104(10) .0327(12) -.0140(10) N3 .0925(16) .0601(12) .1078(17) -.0236(11) .0309(14) -.0047(12) N4 .0658(12) .0683(12) .1054(17) -.0109(10) .0344(12) .0040(12) C5 .0595(13) .0574(13) .0883(16) -.0055(10) .0344(12) -.0049(12) C11 .0455(10) .0461(10) .0554(10) .0005(8) .0160(8) -.0015(8) C12 .0451(10) .0487(10) .0560(10) .0045(8) .0121(8) -.0041(8) C13 .0585(12) .0538(12) .0632(12) .0034(10) .0153(10) .0049(10) C14 .0549(12) .0624(13) .0698(13) -.0045(10) .0183(10) .0054(10) C15 .0436(11) .0705(14) .0706(13) .0020(10) .0139(10) .0047(11) C16 .0472(10) .0565(11) .0604(11) .0047(9) .0135(9) .0024(9) C17 .0499(12) .0618(14) .0785(15) .0071(11) .0114(11) -.0030(12) C18 .0717(17) .091(2) .107(2) -.0164(15) .0253(16) .0242(18) C19 .0628(15) .0777(17) .0893(19) .0156(13) .0142(14) .0190(15) 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 . 1.332(3) yes N1 N2 . 1.349(2) yes N1 C11 . 1.437(2) yes N2 N3 . 1.294(3) yes N3 N4 . 1.351(3) yes N4 C5 . 1.303(3) yes C11 C12 . 1.395(3) yes C11 C16 . 1.395(3) yes C12 C13 . 1.390(3) yes C12 C17 . 1.500(3) no C13 C14 . 1.384(3) yes C14 C15 . 1.386(3) yes C14 C18 . 1.504(3) no C15 C16 . 1.384(3) yes C16 C19 . 1.508(3) no C5 H5 . .98(3) no C13 H13 . .94(3) no C15 H15 . .94(3) no C17 H17A . 1.00(3) no C17 H17B . 1.00(3) no C17 H17C . .94(3) no C18 H18A . .93(3) no C18 H18B . .98(3) no C18 H18C . .95(3) no C19 H19A . .97(3) no C19 H19B . .95(3) no C19 H19C . .89(3) no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .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 107.5(2) yes C5 N1 C11 130.6(2) yes N2 N1 C11 121.9(2) yes N3 N2 N1 106.2(2) yes N2 N3 N4 111.1(2) yes C5 N4 N3 105.3(2) yes N4 C5 N1 110.0(2) yes C12 C11 C16 122.54(18) no C12 C11 N1 118.20(16) no C16 C11 N1 119.26(17) no C13 C12 C11 117.14(18) no C13 C12 C17 120.42(19) no C11 C12 C17 122.44(18) no C14 C13 C12 122.3(2) no C13 C14 C15 118.3(2) no C13 C14 C18 120.5(2) no C15 C14 C18 121.2(2) no C16 C15 C14 122.2(2) no C15 C16 C11 117.48(19) no C15 C16 C19 120.7(2) no C11 C16 C19 121.8(2) no N4 C5 H5 127(2) no N1 C5 H5 123(2) no C14 C13 H13 121(2) no C12 C13 H13 117(2) no C16 C15 H15 118(2) no C14 C15 H15 120(2) no C12 C17 H17A 115(2) no C12 C17 H17B 109(2) no H17A C17 H17B 104(2) no C12 C17 H17C 114(2) no H17A C17 H17C 110(2) no H17B C17 H17C 105(2) no C14 C18 H18A 112(2) no C14 C18 H18B 106(2) no H18A C18 H18B 99(2) no C14 C18 H18C 111(2) no H18A C18 H18C 116(3) no H18B C18 H18C 113(2) no C16 C19 H19A 110(2) no C16 C19 H19B 109(2) no H19A C19 H19B 117(2) no C16 C19 H19C 110(2) no H19A C19 H19C 111(3) no H19B C19 H19C 100(3) no 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 C5 H5 N4 2_655 .98(3) 2.43(3) 3.290(3) 147(2) 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_publ_flag C5 N1 N2 N3 .2(3) no C11 N1 N2 N3 -177.7(2) no N1 N2 N3 N4 -.2(3) no N2 N3 N4 C5 .2(3) no N3 N4 C5 N1 .0(3) no N2 N1 C5 N4 -.1(3) no C11 N1 C5 N4 177.6(2) no C5 N1 C11 C12 -67.4(3) no N2 N1 C11 C12 109.9(2) no C5 N1 C11 C16 112.1(3) no N2 N1 C11 C16 -70.6(3) no C16 C11 C12 C13 .3(3) no N1 C11 C12 C13 179.80(17) no C16 C11 C12 C17 -179.26(19) no N1 C11 C12 C17 .2(3) no C11 C12 C13 C14 1.1(3) no C17 C12 C13 C14 -179.3(2) no C12 C13 C14 C15 -1.7(3) no C12 C13 C14 C18 178.2(3) no C13 C14 C15 C16 .9(4) no C18 C14 C15 C16 -178.9(3) no C14 C15 C16 C11 .4(3) no C14 C15 C16 C19 -177.7(2) no C12 C11 C16 C15 -1.0(3) no N1 C11 C16 C15 179.49(18) no C12 C11 C16 C19 177.0(2) no N1 C11 C16 C19 -2.4(3) no _cod_database_fobs_code 2010589