#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229333.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_2229333
loop_
_publ_author_name
'Barryala, Yamna'
'Massip, Stéphane'
'Lazar, Saïd'
'Essassi, El Mokhtar'
'Zouihri, Hafid'
_publ_section_title
;
 Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetate
;
_journal_coeditor_code           BT5472
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o724
_journal_paper_doi               10.1107/S1600536811006477
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C11 H11 N O3 S'
_chemical_formula_moiety         'C11 H11 N O3 S'
_chemical_formula_sum            'C11 H11 N O3 S'
_chemical_formula_weight         237.27
_chemical_name_systematic
;
Methyl 2-(3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl)acetate
;
_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                 98.71(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.347(5)
_cell_length_b                   8.724(2)
_cell_length_c                   7.2740(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      35.0
_cell_measurement_theta_min      25.0
_cell_volume                     1088.1(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1852
_diffrn_reflns_theta_full        64.92
_diffrn_reflns_theta_max         64.92
_diffrn_reflns_theta_min         2.58
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.592
_exptl_absorpt_correction_T_max  0.6972
_exptl_absorpt_correction_T_min  0.6252
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.275
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0433
_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)+(0.0891P)²+0.2952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                1654
_reflns_number_total             1852
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5472.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229333
_cod_database_fobs_code          2229333
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
C C1 0.06412(11) 1.0010(2) -0.1876(3) 0.0408(5) Uani d . 1 . .
C C12 0.34845(11) 0.9981(2) -0.1202(3) 0.0425(5) Uani d . 1 . .
C C13 0.38184(11) 1.1551(2) -0.0708(3) 0.0385(5) Uani d . 1 . .
C C16 0.48971(13) 1.3152(3) -0.0896(3) 0.0523(6) Uani d . 1 . .
C C2 0.06020(13) 1.0995(2) -0.3366(3) 0.0462(5) Uani d . 1 . .
C C3 0.12837(14) 1.1575(2) -0.3843(3) 0.0477(5) Uani d . 1 . .
C C4 0.19978(12) 1.1181(2) -0.2852(3) 0.0411(5) Uani d . 1 . .
C C5 0.13542(10) 0.9596(2) -0.0860(2) 0.0342(4) Uani d . 1 . .
C C6 0.20474(10) 1.0183(2) -0.1350(2) 0.0325(4) Uani d . 1 . .
C C8 0.29001(11) 0.9244(2) 0.1449(3) 0.0424(5) Uani d . 1 . .
C C9 0.22014(12) 0.9212(3) 0.2432(3) 0.0480(5) Uani d . 1 . .
H H1 0.0183 0.9615 -0.1545 0.049 Uiso calc R 1 . .
H H12A 0.3363 0.9889 -0.2544 0.051 Uiso calc R 1 . .
H H12B 0.3870 0.9207 -0.0761 0.051 Uiso calc R 1 . .
H H16A 0.4570 1.3905 -0.1589 0.078 Uiso calc R 1 . .
H H16B 0.5394 1.3128 -0.1325 0.078 Uiso calc R 1 . .
H H16C 0.4970 1.3413 0.0401 0.078 Uiso calc R 1 . .
H H2 0.0122 1.1265 -0.4041 0.055 Uiso calc R 1 . .
H H3 0.1262 1.2242 -0.4847 0.057 Uiso calc R 1 . .
H H4 0.2451 1.1588 -0.3192 0.049 Uiso calc R 1 . .
H H9A 0.2064 1.0251 0.2730 0.058 Uiso calc R 1 . .
H H9B 0.2327 0.8649 0.3589 0.058 Uiso calc R 1 . .
N N7 0.27801(9) 0.97159(18) -0.0378(2) 0.0371(4) Uani d . 1 . .
O O11 0.35438(9) 0.8896(2) 0.2240(2) 0.0645(5) Uani d . 1 . .
O O14 0.34929(8) 1.25486(18) -0.0003(2) 0.0561(5) Uani d . 1 . .
O O15 0.45320(8) 1.16608(16) -0.1160(2) 0.0454(4) Uani d . 1 . .
S S10 0.13827(3) 0.83215(6) 0.10137(7) 0.0470(3) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C5 S10 C9 . . 95.67(10) ?
C13 O15 C16 . . 115.88(16) ?
C6 N7 C8 . . 124.10(15) ?
C6 N7 C12 . . 119.55(15) ?
C8 N7 C12 . . 115.50(16) ?
C2 C1 C5 . . 121.00(18) ?
C1 C2 C3 . . 119.0(2) ?
C2 C3 C4 . . 120.93(19) ?
C3 C4 C6 . . 120.73(19) ?
S10 C5 C1 . . 119.76(14) ?
S10 C5 C6 . . 120.32(13) ?
C1 C5 C6 . . 119.92(15) ?
N7 C6 C4 . . 121.09(16) ?
N7 C6 C5 . . 120.47(14) ?
C4 C6 C5 . . 118.39(16) ?
O11 C8 N7 . . 121.72(18) ?
O11 C8 C9 . . 121.43(19) ?
N7 C8 C9 . . 116.83(17) ?
S10 C9 C8 . . 111.08(15) ?
N7 C12 C13 . . 111.18(16) ?
O14 C13 O15 . . 124.83(17) ?
O14 C13 C12 . . 125.04(18) ?
O15 C13 C12 . . 110.13(16) ?
C2 C1 H1 . . 119.00 ?
C5 C1 H1 . . 120.00 ?
C1 C2 H2 . . 120.00 ?
C3 C2 H2 . . 121.00 ?
C2 C3 H3 . . 120.00 ?
C4 C3 H3 . . 120.00 ?
C3 C4 H4 . . 120.00 ?
C6 C4 H4 . . 120.00 ?
S10 C9 H9A . . 109.00 ?
S10 C9 H9B . . 109.00 ?
C8 C9 H9A . . 109.00 ?
C8 C9 H9B . . 109.00 ?
H9A C9 H9B . . 108.00 ?
N7 C12 H12A . . 109.00 ?
N7 C12 H12B . . 109.00 ?
C13 C12 H12A . . 109.00 ?
C13 C12 H12B . . 109.00 ?
H12A C12 H12B . . 108.00 ?
O15 C16 H16A . . 109.00 ?
O15 C16 H16B . . 109.00 ?
O15 C16 H16C . . 109.00 ?
H16A C16 H16B . . 109.00 ?
H16A C16 H16C . . 109.00 ?
H16B C16 H16C . . 109.00 ?
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
S10 C5 . 1.7538(17) ?
S10 C9 . 1.800(2) ?
O11 C8 . 1.215(3) ?
O14 C13 . 1.195(2) ?
O15 C13 . 1.332(2) ?
O15 C16 . 1.447(3) ?
N7 C6 . 1.418(2) ?
N7 C8 . 1.377(3) ?
N7 C12 . 1.459(3) ?
C1 C2 . 1.377(3) ?
C1 C5 . 1.389(3) ?
C2 C3 . 1.378(3) ?
C3 C4 . 1.379(3) ?
C4 C6 . 1.390(3) ?
C5 C6 . 1.402(2) ?
C8 C9 . 1.498(3) ?
C12 C13 . 1.509(3) ?
C1 H1 . 0.9300 ?
C2 H2 . 0.9300 ?
C3 H3 . 0.9300 ?
C4 H4 . 0.9300 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 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
C4 H4 O14 5_574 0.93 2.51 3.411(3) 164 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2018387
