#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/68/2016842.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_2016842
loop_
_publ_author_name
'Karczmarzyk, Zbigniew'
_publ_section_title
;Keto--enol tautomerism in crystals of
 3-[hydroxy(phenyl)methyl]-2,5,7-trimethyl-2,3-dihydropyrido[3,2-e][1,2]thiazin-4-one
 1,1-dioxide and
 3-(1-hydroxyethylidene)-2,5,7-trimethyl-2,3-dihydropyrido[3,2-e][1,2]thiazin-4-one
 1,1-dioxide
;
_journal_coeditor_code           SF3092
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o590
_journal_page_last               o594
_journal_paper_doi               10.1107/S010827010803206X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C12 H14 N2 O4 S'
_chemical_formula_moiety         'C12 H14 N2 O4 S'
_chemical_formula_sum            'C12 H14 N2 O4 S'
_chemical_formula_weight         282.31
_chemical_melting_point_gt       430
_chemical_melting_point_lt       431
_chemical_name_systematic
;
3-(1-hydroxyethylidene)-2,5,7-trimethyl-2,3-
dihydropyrido[3,2-e][1,2]thiazin-4-one 1,1-dioxide
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.817(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9023(2)
_cell_length_b                   14.3095(3)
_cell_length_c                   10.6151(2)
_cell_measurement_reflns_used    655
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.03
_cell_measurement_theta_min      2.44
_cell_volume                     1301.03(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD diffractometer'
_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  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18200
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.9353
_exptl_absorpt_correction_T_min  0.8459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0343
_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)+(0.0767P)²+0.3499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2924
_reflns_number_total             3097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sf3092.cif
_cod_data_source_block           II
_cod_database_code               2016842
_cod_database_fobs_code          2016842
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
S S1 0.28260(3) 0.14502(2) 0.18428(3) 0.03286(12) Uani d . 1
O O1 0.17725(12) 0.13514(8) 0.05708(11) 0.0469(3) Uani d . 1
O O2 0.22927(14) 0.12979(8) 0.29738(12) 0.0502(3) Uani d . 1
O O4 0.60624(13) 0.21362(7) -0.02493(10) 0.0442(3) Uani d . 1
O O11 0.47345(16) 0.37005(9) -0.06704(13) 0.0577(3) Uani d . 1
H H11 0.540(3) 0.3110(18) -0.073(2) 0.086 Uiso d . 1
N N2 0.36000(13) 0.24909(8) 0.19434(10) 0.0336(2) Uani d . 1
N N8 0.44934(13) -0.00838(8) 0.25020(11) 0.0370(2) Uani d . 1
C C3 0.43629(15) 0.26669(8) 0.09335(12) 0.0324(3) Uani d . 1
C C4 0.53793(14) 0.19841(8) 0.06382(12) 0.0320(2) Uani d . 1
C C5 0.69129(14) 0.04840(9) 0.14072(13) 0.0358(3) Uani d . 1
C C6 0.69227(16) -0.03689(10) 0.20326(15) 0.0417(3) Uani d . 1
H H61 0.7759 -0.0772 0.2097 0.063 Uiso calc R 1
C C7 0.57315(16) -0.06414(9) 0.25649(14) 0.0398(3) Uani d . 1
C C9 0.44785(13) 0.07307(8) 0.19047(11) 0.0302(2) Uani d . 1
C C10 0.56086(13) 0.10681(8) 0.13238(11) 0.0301(2) Uani d . 1
C C11 0.40557(18) 0.35039(9) 0.02374(15) 0.0420(3) Uani d . 1
C C12 0.2961(2) 0.42230(12) 0.0472(2) 0.0625(5) Uani d . 1
H H121 0.2641 0.4060 0.1237 0.094 Uiso calc R 1
H H122 0.2061 0.4254 -0.0271 0.094 Uiso calc R 1
H H123 0.3473 0.4820 0.0602 0.094 Uiso calc R 1
C C21 0.4427(2) 0.28239(13) 0.32623(16) 0.0569(4) Uani d . 1
H H211 0.3877 0.2623 0.3876 0.085 Uiso calc R 1
H H212 0.4477 0.3494 0.3261 0.085 Uiso calc R 1
H H213 0.5466 0.2572 0.3510 0.085 Uiso calc R 1
C C51 0.82791(18) 0.07409(11) 0.09064(18) 0.0505(4) Uani d . 1
H H511 0.8571 0.1378 0.1134 0.076 Uiso calc R 1
H H512 0.7998 0.0672 -0.0028 0.076 Uiso calc R 1
H H513 0.9143 0.0337 0.1293 0.076 Uiso calc R 1
C C71 0.5784(2) -0.15489(12) 0.3278(2) 0.0588(4) Uani d . 1
H H711 0.6142 -0.1440 0.4204 0.088 Uiso calc R 1
H H712 0.6485 -0.1970 0.3020 0.088 Uiso calc R 1
H H713 0.4757 -0.1818 0.3067 0.088 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'
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
_geom_angle_publ_flag
O2 S1 O1 119.95(7) ?
O2 S1 N2 108.46(6) ?
O1 S1 N2 108.03(6) ?
O2 S1 C9 110.01(6) ?
O1 S1 C9 107.52(6) ?
N2 S1 C9 101.25(5) ?
C11 O11 H11 105.0(13) ?
C3 N2 C21 115.89(11) ?
C3 N2 S1 112.80(8) ?
C21 N2 S1 116.76(10) ?
C9 N8 C7 116.48(11) ?
C11 C3 C4 121.15(11) ?
C11 C3 N2 118.74(11) ?
C4 C3 N2 120.09(10) ?
O4 C4 C3 120.45(11) ?
O4 C4 C10 118.96(11) ?
C3 C4 C10 120.55(10) ?
C6 C5 C10 116.59(11) ?
C6 C5 C51 119.01(12) ?
C10 C5 C51 124.36(12) ?
C7 C6 C5 122.43(12) ?
C7 C6 H61 118.8 ?
C5 C6 H61 118.8 ?
N8 C7 C6 121.30(12) ?
N8 C7 C71 116.79(13) ?
C6 C7 C71 121.88(13) ?
N8 C9 C10 126.79(11) ?
N8 C9 S1 115.23(9) ?
C10 C9 S1 117.98(9) ?
C9 C10 C5 116.40(11) ?
C9 C10 C4 120.01(10) ?
C5 C10 C4 123.57(11) ?
O11 C11 C3 120.99(13) ?
O11 C11 C12 115.69(13) yes
C3 C11 C12 123.31(13) yes
C11 C12 H121 109.5 ?
C11 C12 H122 109.5 ?
H121 C12 H122 109.5 ?
C11 C12 H123 109.5 ?
H121 C12 H123 109.5 ?
H122 C12 H123 109.5 ?
N2 C21 H211 109.5 ?
N2 C21 H212 109.5 ?
H211 C21 H212 109.5 ?
N2 C21 H213 109.5 ?
H211 C21 H213 109.5 ?
H212 C21 H213 109.5 ?
C5 C51 H511 109.5 ?
C5 C51 H512 109.5 ?
H511 C51 H512 109.5 ?
C5 C51 H513 109.5 ?
H511 C51 H513 109.5 ?
H512 C51 H513 109.5 ?
C7 C71 H711 109.5 ?
C7 C71 H712 109.5 ?
H711 C71 H712 109.5 ?
C7 C71 H713 109.5 ?
H711 C71 H713 109.5 ?
H712 C71 H713 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.4230(10) ?
S1 O1 1.4256(11) ?
S1 N2 1.6320(11) ?
S1 C9 1.7821(12) ?
O4 C4 1.2717(14) yes
O11 C11 1.3001(17) yes
O11 H11 1.05(3) ?
N2 C3 1.4389(15) ?
N2 C21 1.4722(18) ?
N8 C9 1.3251(16) ?
N8 C7 1.3476(17) ?
C3 C11 1.3948(18) yes
C3 C4 1.4234(16) yes
C4 C10 1.4861(16) ?
C5 C6 1.3882(19) ?
C5 C10 1.4138(17) ?
C5 C51 1.4997(18) ?
C6 C7 1.387(2) ?
C6 H61 0.9300 ?
C7 C71 1.4974(19) ?
C9 C10 1.4013(16) ?
C11 C12 1.484(2) ?
C12 H121 0.9600 ?
C12 H122 0.9600 ?
C12 H123 0.9600 ?
C21 H211 0.9600 ?
C21 H212 0.9600 ?
C21 H213 0.9600 ?
C51 H511 0.9600 ?
C51 H512 0.9600 ?
C51 H513 0.9600 ?
C71 H711 0.9600 ?
C71 H712 0.9600 ?
C71 H713 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
_geom_hbond_publ_flag
O11 H11 O4 . 1.04(3) 1.55(3) 2.5139(17) 152(2) y
O11 H11 O2 4_665 1.04(3) 2.59(3) 3.0074(19) 103.3(16) y
C12 H122 CgB 4_454 0.96 2.97 3.820(2) 149 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
_geom_torsion_publ_flag
O2 S1 N2 C3 172.20(9) ?
O1 S1 N2 C3 -56.34(10) ?
C9 S1 N2 C3 56.46(10) ?
O2 S1 N2 C21 34.25(13) ?
O1 S1 N2 C21 165.71(11) ?
C9 S1 N2 C21 -81.49(12) ?
C21 N2 C3 C11 -89.34(17) ?
S1 N2 C3 C11 132.32(12) ?
C21 N2 C3 C4 92.18(16) ?
S1 N2 C3 C4 -46.15(15) ?
C11 C3 C4 O4 1.8(2) ?
N2 C3 C4 O4 -179.72(12) ?
C11 C3 C4 C10 -175.67(12) ?
N2 C3 C4 C10 2.76(18) yes
C10 C5 C6 C7 -0.6(2) ?
C51 C5 C6 C7 177.55(14) ?
C9 N8 C7 C6 0.2(2) ?
C9 N8 C7 C71 177.99(14) ?
C5 C6 C7 N8 -0.1(2) ?
C5 C6 C7 C71 -177.83(15) ?
C7 N8 C9 C10 0.55(19) ?
C7 N8 C9 S1 -179.89(10) ?
O2 S1 C9 N8 31.82(12) ?
O1 S1 C9 N8 -100.41(10) ?
N2 S1 C9 N8 146.41(9) ?
O2 S1 C9 C10 -148.58(10) ?
O1 S1 C9 C10 79.19(11) ?
N2 S1 C9 C10 -34.00(11) ?
N8 C9 C10 C5 -1.27(19) ?
S1 C9 C10 C5 179.18(9) ?
N8 C9 C10 C4 177.25(12) ?
S1 C9 C10 C4 -2.29(15) yes
C6 C5 C10 C9 1.20(18) ?
C51 C5 C10 C9 -176.84(13) ?
C6 C5 C10 C4 -177.27(12) ?
C51 C5 C10 C4 4.7(2) ?
O4 C4 C10 C9 -155.33(12) ?
C3 C4 C10 C9 22.23(17) ?
O4 C4 C10 C5 23.09(18) ?
C3 C4 C10 C5 -159.36(12) ?
C4 C3 C11 O11 -2.6(2) ?
N2 C3 C11 O11 178.97(14) ?
C4 C3 C11 C12 177.65(16) ?
N2 C3 C11 C12 -0.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231291
