#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017886.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017886
loop_
_publ_author_name
'Gutierrez, Julio'
'Eisenberg, Rodney'
'Herrensmith, Gabrielle'
'Tobin, Thomas'
'Li, Tonglei'
'Long, Sihui'
_publ_section_title
;
 Polymorphism in
 2-(4-hydroxy-2,6-dimethylanilino)-5,6-dihydro-4H-1,3-thiazin-3-ium
 chloride
;
_journal_coeditor_code           FG3203
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o593
_journal_page_last               o595
_journal_paper_doi               10.1107/S0108270110045099
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H17 N2 O S + , Cl -'
_chemical_formula_moiety         'C12 H17 N2 O S +, Cl -'
_chemical_formula_sum            'C12 H17 Cl N2 O S'
_chemical_formula_weight         272.79
_chemical_name_systematic
;
2-(4-hydroxy-2,6-dimethylanilino)-5,6-dihydro-4H-1,3-thiazin-3-ium
chloride
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.0242(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8877(2)
_cell_length_b                   9.2120(2)
_cell_length_c                   12.6673(3)
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     1370.02(5)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and local procedures'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6046
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.9594
_exptl_absorpt_correction_T_min  0.8184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0419
_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)+(0.0534P)²+0.5868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                2389
_reflns_number_total             3141
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3203.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017886
_cod_database_fobs_code          2017886
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 0.26830(4) 0.87420(5) 0.70402(4) 0.01887(15) Uani d . 1 . .
O O4 -0.19758(11) 0.58513(17) 0.64205(11) 0.0213(3) Uani d . 1 . .
H H4 -0.2399 0.6219 0.5919 0.032 Uiso calc R 1 . .
N N2 0.25741(14) 0.63610(17) 0.59182(13) 0.0177(4) Uani d . 1 . .
H H2 0.2845 0.5673 0.5574 0.021 Uiso calc R 1 . .
N N3 0.43335(13) 0.74466(18) 0.61184(13) 0.0166(4) Uani d . 1 . .
H H3 0.4541 0.6768 0.5724 0.020 Uiso calc R 1 . .
C C2 0.32677(17) 0.7434(2) 0.62978(15) 0.0160(4) Uani d . 1 . .
C C4 0.51844(17) 0.8530(2) 0.65420(17) 0.0177(4) Uani d . 1 . .
H H4A 0.5797 0.8531 0.6118 0.021 Uiso calc R 1 . .
H H4B 0.5505 0.8280 0.7271 0.021 Uiso calc R 1 . .
C C5 0.46578(17) 1.0029(2) 0.65208(17) 0.0194(4) Uani d . 1 . .
H H5A 0.4280 1.0246 0.5803 0.023 Uiso calc R 1 . .
H H5B 0.5252 1.0746 0.6717 0.023 Uiso calc R 1 . .
C C6 0.38039(17) 1.0115(2) 0.72899(17) 0.0213(5) Uani d . 1 . .
H H6A 0.3456 1.1070 0.7236 0.026 Uiso calc R 1 . .
H H6B 0.4203 1.0001 0.8014 0.026 Uiso calc R 1 . .
C C11 0.13924(16) 0.6285(2) 0.60511(16) 0.0153(4) Uani d . 1 . .
C C12 0.05724(17) 0.7029(2) 0.53393(15) 0.0170(4) Uani d . 1 . .
C C13 -0.05634(17) 0.6893(2) 0.54664(15) 0.0172(4) Uani d . 1 . .
H H13 -0.1123 0.7388 0.5009 0.021 Uiso calc R 1 . .
C C14 -0.08699(16) 0.6022(2) 0.62725(15) 0.0162(4) Uani d . 1 . .
C C15 -0.00477(17) 0.5284(2) 0.69634(15) 0.0172(4) Uani d . 1 . .
H H15 -0.0263 0.4704 0.7498 0.021 Uiso calc R 1 . .
C C16 0.10955(17) 0.5402(2) 0.68661(15) 0.0164(4) Uani d . 1 . .
C C17 0.09010(19) 0.7947(3) 0.44518(17) 0.0247(5) Uani d . 1 . .
H H17A 0.0230 0.8204 0.3963 0.037 Uiso calc R 1 . .
H H17B 0.1408 0.7408 0.4079 0.037 Uiso calc R 1 . .
H H17C 0.1274 0.8813 0.4747 0.037 Uiso calc R 1 . .
C C18 0.19913(17) 0.4591(2) 0.76046(17) 0.0219(5) Uani d . 1 . .
H H18A 0.1637 0.4040 0.8106 0.033 Uiso calc R 1 . .
H H18B 0.2521 0.5268 0.7984 0.033 Uiso calc R 1 . .
H H18C 0.2389 0.3945 0.7196 0.033 Uiso calc R 1 . .
Cl Cl1 0.38915(4) 0.35624(5) 0.54403(4) 0.01989(15) 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'
Cl Cl 0.1484 0.1585 '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
C2 S1 C6 . . 103.33(10) ?
C14 O4 H4 . . 109.5 ?
C2 N2 C11 . . 123.66(16) ?
C2 N2 H2 . . 118.2 ?
C11 N2 H2 . . 118.2 ?
C2 N3 C4 . . 124.70(16) ?
C2 N3 H3 . . 117.6 ?
C4 N3 H3 . . 117.6 ?
N3 C2 N2 . . 120.09(17) ?
N3 C2 S1 . . 124.21(15) ?
N2 C2 S1 . . 115.69(15) ?
N3 C4 C5 . . 110.84(16) ?
N3 C4 H4A . . 109.5 ?
C5 C4 H4A . . 109.5 ?
N3 C4 H4B . . 109.5 ?
C5 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C4 C5 C6 . . 110.68(17) ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C5 C6 S1 . . 113.33(14) ?
C5 C6 H6A . . 108.9 ?
S1 C6 H6A . . 108.9 ?
C5 C6 H6B . . 108.9 ?
S1 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
C12 C11 C16 . . 121.89(18) ?
C12 C11 N2 . . 119.61(17) ?
C16 C11 N2 . . 118.43(17) ?
C13 C12 C11 . . 118.20(18) ?
C13 C12 C17 . . 120.48(18) ?
C11 C12 C17 . . 121.32(18) ?
C12 C13 C14 . . 120.51(18) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
O4 C14 C15 . . 117.15(17) ?
O4 C14 C13 . . 122.38(18) ?
C15 C14 C13 . . 120.47(18) ?
C14 C15 C16 . . 120.66(18) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 118.26(18) ?
C15 C16 C18 . . 120.96(18) ?
C11 C16 C18 . . 120.77(18) ?
C12 C17 H17A . . 109.5 ?
C12 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C12 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 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 . 1.739(2) ?
S1 C6 . 1.828(2) ?
O4 C14 . 1.366(2) ?
O4 H4 . 0.8200 ?
N2 C2 . 1.328(2) ?
N2 C11 . 1.443(2) ?
N2 H2 . 0.8600 ?
N3 C2 . 1.322(2) ?
N3 C4 . 1.462(2) ?
N3 H3 . 0.8600 ?
C4 C5 . 1.514(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.515(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C11 C12 . 1.399(3) ?
C11 C16 . 1.403(3) ?
C12 C13 . 1.390(3) ?
C12 C17 . 1.506(3) ?
C13 C14 . 1.392(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.384(3) ?
C15 C16 . 1.388(3) ?
C15 H15 . 0.9300 ?
C16 C18 . 1.502(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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 H2 Cl1 . 0.86 2.33 3.1245(17) 154
N3 H3 Cl1 3_666 0.86 2.57 3.2437(17) 136
O4 H4 Cl1 3_566 0.82 2.28 3.0579(14) 159
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
C4 N3 C2 N2 . . . . -176.75(17) ?
C4 N3 C2 S1 . . . . 2.0(3) ?
C11 N2 C2 N3 . . . . -178.18(17) ?
C11 N2 C2 S1 . . . . 3.0(2) ?
C6 S1 C2 N3 . . . . 7.4(2) ?
C6 S1 C2 N2 . . . . -173.80(15) ?
C2 N3 C4 C5 . . . . -39.1(3) ?
N3 C4 C5 C6 . . . . 66.5(2) ?
C4 C5 C6 S1 . . . . -56.1(2) ?
C2 S1 C6 C5 . . . . 19.88(18) ?
C2 N2 C11 C12 . . . . 84.1(2) ?
C2 N2 C11 C16 . . . . -99.1(2) ?
C16 C11 C12 C13 . . . . 1.0(3) ?
N2 C11 C12 C13 . . . . 177.78(17) ?
C16 C11 C12 C17 . . . . -178.56(18) ?
N2 C11 C12 C17 . . . . -1.8(3) ?
C11 C12 C13 C14 . . . . -0.9(3) ?
C17 C12 C13 C14 . . . . 178.68(18) ?
C12 C13 C14 O4 . . . . -179.57(18) ?
C12 C13 C14 C15 . . . . 0.4(3) ?
O4 C14 C15 C16 . . . . -179.95(17) ?
C13 C14 C15 C16 . . . . 0.1(3) ?
C14 C15 C16 C11 . . . . 0.0(3) ?
C14 C15 C16 C18 . . . . -179.26(18) ?
C12 C11 C16 C15 . . . . -0.6(3) ?
N2 C11 C16 C15 . . . . -177.36(16) ?
C12 C11 C16 C18 . . . . 178.68(18) ?
N2 C11 C16 C18 . . . . 1.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654270
