#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/20/2232086.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_2232086
loop_
_publ_author_name
'Braim, Rostam R.'
'Aziz Ketuly, Kamal'
'A. Hadi, A. Hamid'
'Khaledi, Hamid'
_publ_section_title
;
 2-(4-Chlorophenyl)-3,5-dimethyl-1λ⁶,2-thiazine-1,1-dione
;
_journal_coeditor_code           VM2124
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2775
_journal_paper_doi               10.1107/S1600536811038852
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H12 Cl N O2 S'
_chemical_formula_moiety         'C12 H12 Cl N O2 S'
_chemical_formula_sum            'C12 H12 Cl N O2 S'
_chemical_formula_weight         269.74
_chemical_name_systematic
;
2-(4-Chlorophenyl)-3,5-dimethyl-1λ⁶,2-thiazine-1,1-dione
;
_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                 108.4503(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.22370(10)
_cell_length_b                   15.1606(2)
_cell_length_c                   7.87520(10)
_cell_measurement_reflns_used    4756
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.69
_cell_volume                     1271.15(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97  (Sheldrick, 2008) and 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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11365
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.9188
_exptl_absorpt_correction_T_min  0.8836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0375P)²+0.7004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                2447
_reflns_number_total             2768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            vm2124.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232086
_cod_database_fobs_code          2232086
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_symmetry_multiplicity
Cl Cl1 1.15452(4) 0.78261(3) 0.78766(6) 0.03679(13) Uani d . 1 1
S S1 0.67185(3) 0.54702(2) 0.90462(5) 0.01583(10) Uani d . 1 1
O O1 0.57169(10) 0.60996(7) 0.84129(15) 0.0224(2) Uani d . 1 1
O O2 0.76889(10) 0.56910(7) 1.06785(14) 0.0236(2) Uani d . 1 1
N N1 0.73994(11) 0.53279(8) 0.74623(16) 0.0169(3) Uani d . 1 1
C C1 0.72390(16) 0.49244(12) 0.4367(2) 0.0266(4) Uani d . 1 1
H H1A 0.6744 0.4541 0.3397 0.040 Uiso calc R 1 1
H H1B 0.8133 0.4784 0.4645 0.040 Uiso calc R 1 1
H H1C 0.7095 0.5542 0.3992 0.040 Uiso calc R 1 1
C C2 0.68489(13) 0.47796(10) 0.59948(19) 0.0180(3) Uani d . 1 1
C C3 0.60397(14) 0.41358(10) 0.6087(2) 0.0195(3) Uani d . 1 1
H H3 0.5626 0.3814 0.5029 0.023 Uiso calc R 1 1
C C4 0.57720(13) 0.39124(9) 0.7697(2) 0.0181(3) Uani d . 1 1
C C5 0.51384(16) 0.30477(10) 0.7770(2) 0.0264(3) Uani d . 1 1
H H5A 0.4946 0.3006 0.8898 0.040 Uiso calc R 1 1
H H5B 0.5697 0.2563 0.7697 0.040 Uiso calc R 1 1
H H5C 0.4358 0.3010 0.6763 0.040 Uiso calc R 1 1
C C6 0.61295(13) 0.44386(9) 0.9154(2) 0.0171(3) Uani d . 1 1
H H6 0.6053 0.4233 1.0254 0.021 Uiso calc R 1 1
C C7 0.84013(13) 0.59335(10) 0.75099(19) 0.0173(3) Uani d . 1 1
C C8 0.81380(15) 0.68225(10) 0.7151(2) 0.0233(3) Uani d . 1 1
H H8 0.7297 0.7028 0.6841 0.028 Uiso calc R 1 1
C C9 0.91055(15) 0.74081(11) 0.7247(2) 0.0270(4) Uani d . 1 1
H H9 0.8936 0.8017 0.7006 0.032 Uiso calc R 1 1
C C10 1.03192(15) 0.70909(11) 0.7698(2) 0.0243(3) Uani d . 1 1
C C11 1.05906(14) 0.62056(11) 0.8042(2) 0.0237(3) Uani d . 1 1
H H11 1.1431 0.6000 0.8337 0.028 Uiso calc R 1 1
C C12 0.96219(14) 0.56223(10) 0.7952(2) 0.0202(3) Uani d . 1 1
H H12 0.9794 0.5013 0.8191 0.024 Uiso calc R 1 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'
Cl Cl 0.1484 0.1585 '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
O2 S1 O1 116.33(7)
O2 S1 N1 107.56(6)
O1 S1 N1 108.60(6)
O2 S1 C6 111.35(7)
O1 S1 C6 110.61(7)
N1 S1 C6 101.21(7)
C2 N1 C7 122.44(12)
C2 N1 S1 120.46(10)
C7 N1 S1 115.81(10)
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
C3 C2 N1 120.91(13)
C3 C2 C1 122.43(14)
N1 C2 C1 116.63(13)
C2 C3 C4 123.45(14)
C2 C3 H3 118.3
C4 C3 H3 118.3
C6 C4 C3 121.54(13)
C6 C4 C5 120.04(14)
C3 C4 C5 118.34(13)
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 S1 120.91(12)
C4 C6 H6 119.5
S1 C6 H6 119.5
C12 C7 C8 120.75(14)
C12 C7 N1 119.36(13)
C8 C7 N1 119.87(13)
C9 C8 C7 119.85(14)
C9 C8 H8 120.1
C7 C8 H8 120.1
C10 C9 C8 118.88(15)
C10 C9 H9 120.6
C8 C9 H9 120.6
C9 C10 C11 121.75(15)
C9 C10 Cl1 119.19(13)
C11 C10 Cl1 119.05(12)
C10 C11 C12 119.23(14)
C10 C11 H11 120.4
C12 C11 H11 120.4
C7 C12 C11 119.54(14)
C7 C12 H12 120.2
C11 C12 H12 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C10 1.7416(16)
S1 O2 1.4369(11)
S1 O1 1.4382(11)
S1 N1 1.6703(12)
S1 C6 1.7104(14)
N1 C2 1.3987(19)
N1 C7 1.4430(18)
C1 C2 1.496(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.351(2)
C3 C4 1.433(2)
C3 H3 0.9500
C4 C6 1.350(2)
C4 C5 1.501(2)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 H6 0.9500
C7 C12 1.385(2)
C7 C8 1.390(2)
C8 C9 1.386(2)
C8 H8 0.9500
C9 C10 1.381(2)
C9 H9 0.9500
C10 C11 1.384(2)
C11 C12 1.386(2)
C11 H11 0.9500
C12 H12 0.9500
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
C6 H6 O1 3_667 0.95 2.57 3.3384(18) 137.8
C9 H9 O2 4_575 0.95 2.44 3.3339(19) 156.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9229884
