#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/94/2229413.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_2229413
loop_
_publ_author_name
'Maharramov, Abel M.'
'Khalilov, Ali N.'
'Gurbanov, Atash V.'
'Allahverdiyev, Mirze A.'
'Ng, Seik Weng'
_publ_section_title
;
 4-(2,4,6-Trimethylbenzyl)-1,3-thiazol-2-amine
;
_journal_coeditor_code           IM2269
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o721
_journal_paper_doi               10.1107/S1600536811006386
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H16 N2 S'
_chemical_formula_moiety         'C13 H16 N2 S'
_chemical_formula_sum            'C13 H16 N2 S'
_chemical_formula_weight         232.34
_chemical_name_systematic
;
4-(2,4,6-Trimethylbenzyl)-1,3-thiazol-2-amine
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.0160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5028(5)
_cell_length_b                   30.832(3)
_cell_length_c                   7.8355(7)
_cell_measurement_reflns_used    3598
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      2.6
_cell_volume                     1249.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and 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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7129
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_correction_T_min  0.9331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.6878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1201
_reflns_number_gt                2486
_reflns_number_total             2749
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2269.cif
_cod_data_source_block           I
_cod_original_cell_volume        1249.08(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229413
_cod_database_fobs_code          2229413
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_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 0.65720(8) 0.220399(14) 0.75764(6) 0.02680(15) Uani d . 1 . .
N N1 0.2450(3) 0.26387(5) 0.7802(2) 0.0283(3) Uani d D 1 . .
H H11 0.351(3) 0.2757(6) 0.8795(19) 0.030(5) Uiso d D 1 . .
H H12 0.080(2) 0.2637(8) 0.764(3) 0.038(6) Uiso d D 1 . .
N N2 0.1780(3) 0.20379(5) 0.58369(19) 0.0241(3) Uani d . 1 . .
C C1 0.3278(3) 0.23024(5) 0.7040(2) 0.0215(3) Uani d . 1 . .
C C2 0.5821(3) 0.17807(6) 0.6029(2) 0.0267(4) Uani d . 1 . .
H H2 0.7056 0.1604 0.5759 0.032 Uiso calc R 1 . .
C C3 0.3239(3) 0.17382(5) 0.5263(2) 0.0244(3) Uani d . 1 . .
C C4 0.1797(4) 0.13975(6) 0.3931(3) 0.0338(4) Uani d . 1 . .
H H4A 0.0544 0.1542 0.2862 0.041 Uiso calc R 1 . .
H H4B 0.0800 0.1217 0.4502 0.041 Uiso calc R 1 . .
C C5 0.3520(3) 0.11046(6) 0.3288(2) 0.0282(4) Uani d . 1 . .
C C6 0.3814(4) 0.11748(6) 0.1605(2) 0.0301(4) Uani d . 1 . .
C C7 0.5436(4) 0.09018(7) 0.1069(3) 0.0344(4) Uani d . 1 . .
H H7 0.5633 0.0950 -0.0075 0.041 Uiso calc R 1 . .
C C8 0.6772(4) 0.05629(6) 0.2137(3) 0.0344(4) Uani d . 1 . .
C C9 0.6454(4) 0.04995(6) 0.3799(3) 0.0365(4) Uani d . 1 . .
H H9 0.7352 0.0269 0.4557 0.044 Uiso calc R 1 . .
C C10 0.4858(4) 0.07644(6) 0.4388(3) 0.0336(4) Uani d . 1 . .
C C11 0.2363(5) 0.15279(7) 0.0330(3) 0.0473(6) Uani d . 1 . .
H H11A 0.2694 0.1807 0.0966 0.071 Uiso calc R 1 . .
H H11B 0.0505 0.1465 -0.0085 0.071 Uiso calc R 1 . .
H H11C 0.2946 0.1541 -0.0719 0.071 Uiso calc R 1 . .
C C12 0.8478(4) 0.02682(8) 0.1499(3) 0.0487(6) Uani d . 1 . .
H H12A 0.9348 0.0438 0.0820 0.073 Uiso calc R 1 . .
H H12B 0.7419 0.0042 0.0711 0.073 Uiso calc R 1 . .
H H12C 0.9776 0.0133 0.2552 0.073 Uiso calc R 1 . .
C C13 0.4571(7) 0.06770(8) 0.6208(3) 0.0609(8) Uani d . 1 . .
H H13A 0.5687 0.0434 0.6802 0.091 Uiso calc R 1 . .
H H13B 0.2767 0.0605 0.6029 0.091 Uiso calc R 1 . .
H H13C 0.5074 0.0936 0.6974 0.091 Uiso calc R 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
C2 S1 C1 . . 89.03(8) ?
C1 N1 H11 . . 119.3(14) ?
C1 N1 H12 . . 115.1(16) ?
H11 N1 H12 . . 118(2) ?
C1 N2 C3 . . 110.84(14) ?
N2 C1 N1 . . 125.03(15) ?
N2 C1 S1 . . 114.43(12) ?
N1 C1 S1 . . 120.50(13) ?
C3 C2 S1 . . 110.36(13) ?
C3 C2 H2 . . 124.8 ?
S1 C2 H2 . . 124.8 ?
C2 C3 N2 . . 115.33(15) ?
C2 C3 C4 . . 127.16(16) ?
N2 C3 C4 . . 117.47(15) ?
C3 C4 C5 . . 113.94(15) ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4B . . 108.8 ?
C5 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C10 C5 C6 . . 119.39(17) ?
C10 C5 C4 . . 120.04(17) ?
C6 C5 C4 . . 120.56(17) ?
C5 C6 C7 . . 118.95(17) ?
C5 C6 C11 . . 122.00(18) ?
C7 C6 C11 . . 119.01(18) ?
C8 C7 C6 . . 122.45(18) ?
C8 C7 H7 . . 118.8 ?
C6 C7 H7 . . 118.8 ?
C7 C8 C9 . . 117.63(18) ?
C7 C8 C12 . . 121.1(2) ?
C9 C8 C12 . . 121.3(2) ?
C8 C9 C10 . . 121.79(18) ?
C8 C9 H9 . . 119.1 ?
C10 C9 H9 . . 119.1 ?
C9 C10 C5 . . 119.78(17) ?
C9 C10 C13 . . 119.37(19) ?
C5 C10 C13 . . 120.84(19) ?
C6 C11 H11A . . 109.5 ?
C6 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C6 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C8 C12 H12A . . 109.5 ?
C8 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C8 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
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 C2 . 1.7323(18) ?
S1 C1 . 1.7415(16) ?
N1 C1 . 1.351(2) ?
N1 H11 . 0.880(10) ?
N1 H12 . 0.870(10) ?
N2 C1 . 1.304(2) ?
N2 C3 . 1.396(2) ?
C2 C3 . 1.346(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.502(2) ?
C4 C5 . 1.515(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C10 . 1.397(3) ?
C5 C6 . 1.399(3) ?
C6 C7 . 1.393(3) ?
C6 C11 . 1.508(3) ?
C7 C8 . 1.383(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.386(3) ?
C8 C12 . 1.509(3) ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9500 ?
C10 C13 . 1.512(3) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
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
_geom_hbond_publ_flag
N1 H11 N2 4_666 0.880(10) 2.060(10) 2.907(2) 163(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25808012
