#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/26/2222602.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_2222602
loop_
_publ_author_name
'Xie, An-Yun'
'Ye, Jiao'
'Qin, Zhi'
'Hu, Ai-Xi'
_publ_section_title
;
 4-tert-Butyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine
;
_journal_coeditor_code           BT5018
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2057
_journal_paper_doi               10.1107/S1600536809029912
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C9 H13 N5 S'
_chemical_formula_moiety         'C9 H13 N5 S'
_chemical_formula_sum            'C9 H13 N5 S'
_chemical_formula_weight         223.30
_chemical_melting_point          451
_chemical_name_systematic
;
4-tert-Butyl-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7487(4)
_cell_length_b                   14.2240(8)
_cell_length_c                   10.2697(5)
_cell_measurement_reflns_used    4587
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.45
_cell_volume                     1131.54(10)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6167
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.9092
_exptl_absorpt_correction_T_min  0.8867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0309
_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/[σ²(Fo²)+(0.0539P)²+0.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                2187
_reflns_number_total             2463
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5018.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222602
_cod_database_fobs_code          2222602
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'
loop_
_atom_site_type_symbol
_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
S S1 0.10734(4) 0.36412(2) 0.12795(3) 0.02144(11) Uani d . 1 . .
C C1 0.28446(15) 0.42187(8) 0.06301(12) 0.0208(2) Uani d . 1 . .
C C2 0.38251(15) 0.27348(8) 0.06564(11) 0.0194(2) Uani d . 1 . .
C C3 0.22378(16) 0.25969(8) 0.11582(11) 0.0200(2) Uani d . 1 . .
C C4 0.52048(16) 0.19969(9) 0.03942(13) 0.0248(3) Uani d . 1 . .
C C5 0.69774(19) 0.24700(11) 0.0350(2) 0.0490(5) Uani d . 1 . .
H H5A 0.6994 0.2911 -0.0382 0.073 Uiso calc R 1 . .
H H5B 0.7869 0.1990 0.0239 0.073 Uiso calc R 1 . .
H H5C 0.7203 0.2811 0.1166 0.073 Uiso calc R 1 . .
C C6 0.4799(2) 0.15274(11) -0.09224(15) 0.0392(4) Uani d . 1 . .
H H6A 0.4739 0.2008 -0.1606 0.059 Uiso calc R 1 . .
H H6B 0.3689 0.1200 -0.0885 0.059 Uiso calc R 1 . .
H H6C 0.5711 0.1075 -0.1117 0.059 Uiso calc R 1 . .
C C7 0.5268(2) 0.12361(10) 0.14558(16) 0.0368(3) Uani d . 1 . .
H H7A 0.6247 0.0816 0.1312 0.055 Uiso calc R 1 . .
H H7B 0.4193 0.0873 0.1420 0.055 Uiso calc R 1 . .
H H7C 0.5404 0.1534 0.2313 0.055 Uiso calc R 1 . .
C C8 0.01671(17) 0.04703(9) 0.15964(13) 0.0267(3) Uani d . 1 . .
H H8 -0.0313 -0.0113 0.1318 0.032 Uiso calc R 1 . .
C C9 0.09146(17) 0.15830(9) 0.28121(12) 0.0267(3) Uani d . 1 . .
H H9 0.1101 0.1985 0.3541 0.032 Uiso calc R 1 . .
N N1 0.41461(13) 0.36685(7) 0.03390(10) 0.0210(2) Uani d . 1 . .
N N2 0.27815(14) 0.51513(7) 0.04483(12) 0.0285(3) Uani d . 1 . .
H H2A 0.3661 0.5445 0.0108 0.034 Uiso calc R 1 . .
H H2B 0.1860 0.5469 0.0670 0.034 Uiso calc R 1 . .
N N3 0.14376(13) 0.17666(7) 0.16036(10) 0.0206(2) Uani d . 1 . .
N N4 0.09397(14) 0.10478(8) 0.07907(10) 0.0254(2) Uani d . 1 . .
N N5 0.01069(15) 0.07679(8) 0.28504(11) 0.0299(3) Uani d . 1 . .
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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 S1 C1 . . 87.73(6) ?
N1 C1 N2 . . 125.59(11) ?
N1 C1 S1 . . 114.89(9) ?
N2 C1 S1 . . 119.50(9) ?
C3 C2 N1 . . 113.28(10) ?
C3 C2 C4 . . 127.71(10) ?
N1 C2 C4 . . 118.99(10) ?
C2 C3 N3 . . 130.61(11) ?
C2 C3 S1 . . 112.26(9) ?
N3 C3 S1 . . 117.12(9) ?
C2 C4 C5 . . 109.61(10) ?
C2 C4 C6 . . 109.04(10) ?
C5 C4 C6 . . 109.23(13) ?
C2 C4 C7 . . 111.65(11) ?
C5 C4 C7 . . 108.55(12) ?
C6 C4 C7 . . 108.73(11) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 H6A . . 109.5 ?
C4 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C4 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C4 C7 H7A . . 109.5 ?
C4 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C4 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N4 C8 N5 . . 115.32(11) ?
N4 C8 H8 . . 122.3 ?
N5 C8 H8 . . 122.3 ?
N5 C9 N3 . . 110.70(11) ?
N5 C9 H9 . . 124.6 ?
N3 C9 H9 . . 124.6 ?
C1 N1 C2 . . 111.81(10) ?
C1 N2 H2A . . 120.0 ?
C1 N2 H2B . . 120.0 ?
H2A N2 H2B . . 120.0 ?
C9 N3 N4 . . 109.38(10) ?
C9 N3 C3 . . 127.35(10) ?
N4 N3 C3 . . 123.03(10) ?
C8 N4 N3 . . 101.98(10) ?
C9 N5 C8 . . 102.60(11) ?
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
S1 C3 . 1.7441(12) ?
S1 C1 . 1.7464(12) ?
C1 N1 . 1.3169(16) ?
C1 N2 . 1.3403(16) ?
C2 C3 . 1.3598(17) ?
C2 N1 . 1.3914(14) ?
C2 C4 . 1.5270(16) ?
C3 N3 . 1.4153(15) ?
C4 C5 . 1.5312(19) ?
C4 C6 . 1.533(2) ?
C4 C7 . 1.5360(18) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 N4 . 1.3202(16) ?
C8 N5 . 1.3575(18) ?
C8 H8 . 0.9500 ?
C9 N5 . 1.3187(17) ?
C9 N3 . 1.3410(16) ?
C9 H9 . 0.9500 ?
N2 H2A . 0.8800 ?
N2 H2B . 0.8800 ?
N3 N4 . 1.3692(14) ?
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
N2 H2B N5 2 0.88 2.22 3.0049(16) 148.3
N2 H2A N1 3_665 0.88 2.17 3.0392(14) 167.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 S1 C1 N1 . . . . 1.03(10) ?
C3 S1 C1 N2 . . . . 179.99(11) ?
N1 C2 C3 N3 . . . . -179.45(11) ?
C4 C2 C3 N3 . . . . 1.9(2) ?
N1 C2 C3 S1 . . . . -0.87(13) ?
C4 C2 C3 S1 . . . . -179.52(10) ?
C1 S1 C3 C2 . . . . -0.05(9) ?
C1 S1 C3 N3 . . . . 178.73(10) ?
C3 C2 C4 C5 . . . . -157.79(14) ?
N1 C2 C4 C5 . . . . 23.63(17) ?
C3 C2 C4 C6 . . . . 82.69(16) ?
N1 C2 C4 C6 . . . . -95.90(13) ?
C3 C2 C4 C7 . . . . -37.48(17) ?
N1 C2 C4 C7 . . . . 143.94(12) ?
N2 C1 N1 C2 . . . . 179.41(12) ?
S1 C1 N1 C2 . . . . -1.71(13) ?
C3 C2 N1 C1 . . . . 1.65(15) ?
C4 C2 N1 C1 . . . . -179.57(10) ?
N5 C9 N3 N4 . . . . 0.78(15) ?
N5 C9 N3 C3 . . . . 175.29(12) ?
C2 C3 N3 C9 . . . . 117.79(16) ?
S1 C3 N3 C9 . . . . -60.72(15) ?
C2 C3 N3 N4 . . . . -68.38(18) ?
S1 C3 N3 N4 . . . . 113.10(11) ?
N5 C8 N4 N3 . . . . 1.00(15) ?
C9 N3 N4 C8 . . . . -1.03(14) ?
C3 N3 N4 C8 . . . . -175.83(11) ?
N3 C9 N5 C8 . . . . -0.16(15) ?
N4 C8 N5 C9 . . . . -0.56(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742979
