#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017885.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_2017885
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           2
_space_group_name_Hall           '-P 1'
_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           SHELXL97
_cell_angle_alpha                73.3925(6)
_cell_angle_beta                 84.1579(6)
_cell_angle_gamma                70.8388(6)
_cell_formula_units_Z            2
_cell_length_a                   6.99610(10)
_cell_length_b                   7.94210(10)
_cell_length_c                   13.0864(2)
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.0
_cell_volume                     658.168(16)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5923
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_correction_T_min  0.8807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.277
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0281
_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)+(0.0280P)²+0.3783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                2762
_reflns_number_total             2981
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3203.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2017885
_cod_database_fobs_code          2017885
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 0.33096(5) -0.11563(4) 0.90302(2) 0.01881(9) Uani d . 1 . .
O O4 0.24327(13) 0.72281(12) 0.36708(7) 0.01848(19) Uani d . 1 . .
H H4 0.2369 0.6870 0.3134 0.028 Uiso d R 1 . .
N N2 0.23495(15) 0.17820(14) 0.74414(8) 0.0162(2) Uani d . 1 . .
H H2 0.1171 0.1916 0.7773 0.019 Uiso d R 1 . .
N N3 0.57340(15) 0.01012(14) 0.74502(8) 0.0158(2) Uani d . 1 . .
H H3 0.5868 0.0909 0.6849 0.019 Uiso d R 1 . .
C C2 0.39103(18) 0.03369(16) 0.78804(9) 0.0143(2) Uani d . 1 . .
C C4 0.75611(19) -0.14085(17) 0.78973(10) 0.0198(3) Uani d . 1 . .
H H4A 0.8745 -0.1024 0.7646 0.024 Uiso calc R 1 . .
H H4B 0.7671 -0.2478 0.7651 0.024 Uiso calc R 1 . .
C C5 0.7503(2) -0.1936(2) 0.91032(11) 0.0259(3) Uani d . 1 . .
H H5A 0.7327 -0.0853 0.9351 0.031 Uiso calc R 1 . .
H H5B 0.8779 -0.2849 0.9375 0.031 Uiso calc R 1 . .
C C6 0.5788(2) -0.2721(2) 0.95266(11) 0.0293(3) Uani d . 1 . .
H H6A 0.5769 -0.3014 1.0299 0.035 Uiso calc R 1 . .
H H6B 0.6043 -0.3865 0.9331 0.035 Uiso calc R 1 . .
C C11 0.24705(17) 0.31409(16) 0.64568(9) 0.0139(2) Uani d . 1 . .
C C12 0.24680(17) 0.27297(16) 0.54866(10) 0.0141(2) Uani d . 1 . .
C C13 0.24924(17) 0.40896(16) 0.45421(9) 0.0147(2) Uani d . 1 . .
H H13 0.2524 0.3833 0.3889 0.018 Uiso calc R 1 . .
C C14 0.24696(17) 0.58294(16) 0.45753(9) 0.0148(2) Uani d . 1 . .
C C15 0.24651(17) 0.62147(16) 0.55438(10) 0.0158(2) Uani d . 1 . .
H H15 0.2451 0.7385 0.5553 0.019 Uiso calc R 1 . .
C C16 0.24809(17) 0.48781(16) 0.65008(10) 0.0148(2) Uani d . 1 . .
C C17 0.23777(19) 0.08723(16) 0.54606(10) 0.0176(2) Uani d . 1 . .
H H17A 0.2302 0.0861 0.4734 0.026 Uiso calc R 1 . .
H H17B 0.1203 0.0652 0.5847 0.026 Uiso calc R 1 . .
H H17C 0.3571 -0.0079 0.5783 0.026 Uiso calc R 1 . .
C C18 0.2548(2) 0.52859(18) 0.75508(10) 0.0201(3) Uani d . 1 . .
H H18A 0.3847 0.4595 0.7872 0.030 Uiso calc R 1 . .
H H18B 0.1510 0.4938 0.8017 0.030 Uiso calc R 1 . .
H H18C 0.2331 0.6585 0.7432 0.030 Uiso calc R 1 . .
Cl Cl1 -0.18978(4) 0.32705(4) 0.84515(2) 0.02133(9) 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 . . 102.79(6) ?
C14 O4 H4 . . 109.5 ?
C2 N2 C11 . . 123.96(10) ?
C2 N2 H2 . . 118.0 ?
C11 N2 H2 . . 118.0 ?
C2 N3 C4 . . 124.96(10) ?
C2 N3 H3 . . 117.5 ?
C4 N3 H3 . . 117.5 ?
N3 C2 N2 . . 121.02(11) ?
N3 C2 S1 . . 124.62(9) ?
N2 C2 S1 . . 114.37(9) ?
N3 C4 C5 . . 111.27(10) ?
N3 C4 H4A . . 109.4 ?
C5 C4 H4A . . 109.4 ?
N3 C4 H4B . . 109.4 ?
C5 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C4 C5 C6 . . 110.83(12) ?
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 . . 113.60(9) ?
C5 C6 H6A . . 108.8 ?
S1 C6 H6A . . 108.8 ?
C5 C6 H6B . . 108.8 ?
S1 C6 H6B . . 108.8 ?
H6A C6 H6B . . 107.7 ?
C12 C11 C16 . . 121.82(11) ?
C12 C11 N2 . . 119.48(10) ?
C16 C11 N2 . . 118.61(10) ?
C13 C12 C11 . . 118.70(11) ?
C13 C12 C17 . . 120.48(11) ?
C11 C12 C17 . . 120.80(10) ?
C14 C13 C12 . . 120.01(11) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
O4 C14 C15 . . 117.25(10) ?
O4 C14 C13 . . 122.26(11) ?
C15 C14 C13 . . 120.49(11) ?
C14 C15 C16 . . 120.96(11) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C15 C16 C11 . . 117.99(11) ?
C15 C16 C18 . . 120.68(11) ?
C11 C16 C18 . . 121.32(11) ?
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 . 1.7394(12) ?
S1 C6 . 1.8237(15) ?
O4 C14 . 1.3680(14) ?
O4 H4 . 0.8395 ?
N2 C2 . 1.3296(16) ?
N2 C11 . 1.4405(14) ?
N2 H2 . 0.8803 ?
N3 C2 . 1.3180(16) ?
N3 C4 . 1.4693(15) ?
N3 H3 . 0.8802 ?
C4 C5 . 1.5125(18) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.515(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C11 C12 . 1.3988(17) ?
C11 C16 . 1.3997(16) ?
C12 C13 . 1.3925(16) ?
C12 C17 . 1.5071(16) ?
C13 C14 . 1.3897(16) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.3857(17) ?
C15 C16 . 1.3895(17) ?
C15 H15 . 0.9300 ?
C16 C18 . 1.5076(17) ?
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 . 0.88 2.28 3.1244(11) 161
N3 H3 O4 2_666 0.88 2.12 2.8143(13) 136
O4 H4 Cl1 2_566 0.84 2.17 2.9913(10) 165
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 . . . . 177.58(11) ?
C4 N3 C2 S1 . . . . -2.90(17) ?
C11 N2 C2 N3 . . . . 3.03(18) ?
C11 N2 C2 S1 . . . . -176.54(9) ?
C6 S1 C2 N3 . . . . 9.14(12) ?
C6 S1 C2 N2 . . . . -171.30(10) ?
C2 N3 C4 C5 . . . . -34.24(17) ?
N3 C4 C5 C6 . . . . 64.57(14) ?
C4 C5 C6 S1 . . . . -57.07(14) ?
C2 S1 C6 C5 . . . . 20.83(12) ?
C2 N2 C11 C12 . . . . 78.84(15) ?
C2 N2 C11 C16 . . . . -104.46(13) ?
C16 C11 C12 C13 . . . . 0.50(17) ?
N2 C11 C12 C13 . . . . 177.10(10) ?
C16 C11 C12 C17 . . . . -177.69(11) ?
N2 C11 C12 C17 . . . . -1.09(16) ?
C11 C12 C13 C14 . . . . -1.54(17) ?
C17 C12 C13 C14 . . . . 176.66(11) ?
C12 C13 C14 O4 . . . . -178.06(10) ?
C12 C13 C14 C15 . . . . 1.35(17) ?
O4 C14 C15 C16 . . . . 179.37(10) ?
C13 C14 C15 C16 . . . . -0.07(18) ?
C14 C15 C16 C11 . . . . -0.95(17) ?
C14 C15 C16 C18 . . . . 177.89(11) ?
C12 C11 C16 C15 . . . . 0.74(17) ?
N2 C11 C16 C15 . . . . -175.89(10) ?
C12 C11 C16 C18 . . . . -178.09(11) ?
N2 C11 C16 C18 . . . . 5.28(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654270
