#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/89/2228911.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_2228911
loop_
_publ_author_name
'Zhao, Hua-Rong'
'Meng, Xiang-Wu'
_publ_section_title
;
 (Z)-2-[(2,4-Dimethylphenyl)imino]-1,3-thiazinan-4-one
;
_journal_coeditor_code           XU5100
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o110
_journal_paper_doi               10.1107/S1600536810051147
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H14 N2 O S'
_chemical_formula_moiety         'C12 H14 N2 O S'
_chemical_formula_sum            'C12 H14 N2 O S'
_chemical_formula_weight         234.31
_chemical_name_systematic
;
(Z)-2-[(2,4-Dimethylphenyl)imino]-1,3-thiazinan-4-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.184(7)
_cell_angle_beta                 94.647(5)
_cell_angle_gamma                97.910(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2325(4)
_cell_length_b                   9.2000(7)
_cell_length_c                   10.0513(7)
_cell_measurement_reflns_used    1436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      2.8
_cell_volume                     597.27(8)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur Atlas Gemini ultra'
_diffrn_measurement_method       'ω scans'
_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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4061
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0477
_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)+(0.0414P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                1569
_reflns_number_total             2188
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5100.cif
_cod_data_source_block           I
_cod_original_cell_volume        597.27(7)
_cod_database_code               2228911
_cod_database_fobs_code          2228911
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.55185(9) 0.52363(7) 0.33010(8) 0.0523(3) Uani d . 1 . .
O O1 0.8076(2) 1.03840(19) 0.5892(2) 0.0549(5) Uani d . 1 . .
N N1 0.9131(3) 0.5481(2) 0.2917(2) 0.0440(5) Uani d . 1 . .
N N2 0.8280(3) 0.7918(2) 0.4195(2) 0.0421(5) Uani d . 1 . .
H H2 0.9236 0.8376 0.3961 0.051 Uiso calc R 1 . .
C C1 0.7441(4) -0.1475(3) 0.0075(4) 0.0823(11) Uani d . 1 . .
H H1A 0.6145 -0.1836 -0.0386 0.123 Uiso calc R 1 . .
H H1B 0.7650 -0.1892 0.0797 0.123 Uiso calc R 1 . .
H H1C 0.8247 -0.1863 -0.0658 0.123 Uiso calc R 1 . .
C C2 0.7884(3) 0.0354(3) 0.0820(3) 0.0518(7) Uani d . 1 . .
C C3 0.8622(4) 0.1187(3) 0.2294(3) 0.0580(8) Uani d . 1 . .
H H3 0.8850 0.0615 0.2848 0.070 Uiso calc R 1 . .
C C4 0.9027(4) 0.2862(3) 0.2960(3) 0.0501(7) Uani d . 1 . .
H H4 0.9552 0.3403 0.3952 0.060 Uiso calc R 1 . .
C C5 0.8663(3) 0.3743(3) 0.2171(3) 0.0399(6) Uani d . 1 . .
C C6 0.7938(3) 0.2946(3) 0.0679(3) 0.0445(6) Uani d . 1 . .
C C7 0.7569(3) 0.1258(3) 0.0048(3) 0.0540(8) Uani d . 1 . .
H H7 0.7082 0.0710 -0.0951 0.065 Uiso calc R 1 . .
C C8 0.7535(4) 0.3858(4) -0.0223(3) 0.0680(9) Uani d . 1 . .
H H8B 0.7962 0.3363 -0.1158 0.102 Uiso calc R 1 . .
H H8C 0.8184 0.4964 0.0293 0.102 Uiso calc R 1 . .
H H8A 0.6201 0.3829 -0.0379 0.102 Uiso calc R 1 . .
C C9 0.7833(3) 0.6224(3) 0.3455(3) 0.0360(6) Uani d . 1 . .
C C10 0.4370(3) 0.6924(3) 0.4178(3) 0.0544(7) Uani d . 1 . .
H H10B 0.4074 0.7384 0.3491 0.065 Uiso calc R 1 . .
H H10A 0.3191 0.6545 0.4433 0.065 Uiso calc R 1 . .
C C11 0.5592(3) 0.8223(3) 0.5554(3) 0.0477(7) Uani d . 1 . .
H H11B 0.4893 0.9078 0.6024 0.057 Uiso calc R 1 . .
H H11A 0.5883 0.7760 0.6239 0.057 Uiso calc R 1 . .
C C12 0.7393(3) 0.8938(3) 0.5241(3) 0.0399(6) 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'
O O 0.0106 0.0060 '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
C9 S1 C10 . . 101.58(11) ?
C9 N1 C5 . . 117.4(2) ?
C12 N2 C9 . . 128.4(2) ?
C12 N2 H2 . . 115.8 ?
C9 N2 H2 . . 115.8 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 C3 . . 117.3(2) ?
C7 C2 C1 . . 121.2(3) ?
C3 C2 C1 . . 121.5(3) ?
C2 C3 C4 . . 120.9(3) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.7(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 N1 . . 118.3(2) ?
C6 C5 N1 . . 121.6(2) ?
C5 C6 C7 . . 117.3(3) ?
C5 C6 C8 . . 121.7(2) ?
C7 C6 C8 . . 120.9(2) ?
C2 C7 C6 . . 123.7(3) ?
C2 C7 H7 . . 118.2 ?
C6 C7 H7 . . 118.2 ?
C6 C8 H8B . . 109.5 ?
C6 C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C6 C8 H8A . . 109.5 ?
H8B C8 H8A . . 109.5 ?
H8C C8 H8A . . 109.5 ?
N1 C9 N2 . . 117.8(2) ?
N1 C9 S1 . . 123.15(18) ?
N2 C9 S1 . . 119.04(17) ?
C11 C10 S1 . . 111.74(18) ?
C11 C10 H10B . . 109.3 ?
S1 C10 H10B . . 109.3 ?
C11 C10 H10A . . 109.3 ?
S1 C10 H10A . . 109.3 ?
H10B C10 H10A . . 107.9 ?
C12 C11 C10 . . 112.6(2) ?
C12 C11 H11B . . 109.1 ?
C10 C11 H11B . . 109.1 ?
C12 C11 H11A . . 109.1 ?
C10 C11 H11A . . 109.1 ?
H11B C11 H11A . . 107.8 ?
O1 C12 N2 . . 120.2(2) ?
O1 C12 C11 . . 122.0(2) ?
N2 C12 C11 . . 117.8(2) ?
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 C9 . 1.754(2) ?
S1 C10 . 1.798(3) ?
O1 C12 . 1.223(3) ?
N1 C9 . 1.264(3) ?
N1 C5 . 1.436(3) ?
N2 C12 . 1.365(3) ?
N2 C9 . 1.400(3) ?
N2 H2 . 0.8600 ?
C1 C2 . 1.509(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.378(4) ?
C2 C3 . 1.378(4) ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(3) ?
C6 C7 . 1.391(3) ?
C6 C8 . 1.503(4) ?
C7 H7 . 0.9300 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C8 H8A . 0.9600 ?
C10 C11 . 1.510(3) ?
C10 H10B . 0.9700 ?
C10 H10A . 0.9700 ?
C11 C12 . 1.492(3) ?
C11 H11B . 0.9700 ?
C11 H11A . 0.9700 ?
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
N2 H2 O1 2_776 0.86 2.075 2.900(3) 161 y
C1 H1C Cg2 2_755 0.96 2.716 3.591(3) 152 y
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
C7 C2 C3 C4 . . . . -0.1(4) ?
C1 C2 C3 C4 . . . . 179.7(3) ?
C2 C3 C4 C5 . . . . 1.4(4) ?
C3 C4 C5 C6 . . . . -2.1(4) ?
C3 C4 C5 N1 . . . . -179.4(2) ?
C9 N1 C5 C4 . . . . -94.8(3) ?
C9 N1 C5 C6 . . . . 87.9(3) ?
C4 C5 C6 C7 . . . . 1.4(4) ?
N1 C5 C6 C7 . . . . 178.6(2) ?
C4 C5 C6 C8 . . . . -179.6(2) ?
N1 C5 C6 C8 . . . . -2.4(4) ?
C3 C2 C7 C6 . . . . -0.6(4) ?
C1 C2 C7 C6 . . . . 179.6(2) ?
C5 C6 C7 C2 . . . . 0.0(4) ?
C8 C6 C7 C2 . . . . -179.1(2) ?
C5 N1 C9 N2 . . . . 179.5(2) ?
C5 N1 C9 S1 . . . . -1.1(3) ?
C12 N2 C9 N1 . . . . -156.8(2) ?
C12 N2 C9 S1 . . . . 23.7(3) ?
C10 S1 C9 N1 . . . . -177.0(2) ?
C10 S1 C9 N2 . . . . 2.4(2) ?
C9 S1 C10 C11 . . . . -41.6(2) ?
S1 C10 C11 C12 . . . . 62.2(3) ?
C9 N2 C12 O1 . . . . 172.6(2) ?
C9 N2 C12 C11 . . . . -7.2(4) ?
C10 C11 C12 O1 . . . . 141.7(2) ?
C10 C11 C12 N2 . . . . -38.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656442
