#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239539.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_2239539
loop_
_publ_author_name
'Sebbar, Nada Kheira'
'Zerzouf, Abdelfettah'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 4-(Prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one
;
_journal_coeditor_code           IM2453
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o641
_journal_paper_doi               10.1107/S160053681400943X
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C11 H9 N O S'
_chemical_formula_moiety         'C11 H9 N O S'
_chemical_formula_sum            'C11 H9 N O S'
_chemical_formula_weight         203.25
_chemical_name_systematic
;
4-(Prop-2-ynyl)-2H-1,4-benzothiazin-3(4H)-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.565(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.005(2)
_cell_length_b                   10.889(3)
_cell_length_c                   10.341(3)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      2.69
_cell_volume                     981.4(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and 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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 APEX'
_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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9586
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0332
_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)+(0.0525P)²+0.1971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0971
_reflns_number_gt                2242
_reflns_number_total             2532
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2453sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        981.3(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2239539
_cod_database_fobs_code          2239539
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
_atom_site_symmetry_multiplicity
C C1 0.72598(13) 0.66267(11) 0.41584(11) 0.0349(2) Uani d . 1 1
C C2 0.57459(15) 0.63028(14) 0.40891(14) 0.0468(3) Uani d . 1 1
H H2 0.5255 0.6635 0.4699 0.056 Uiso calc R 1 1
C C3 0.49680(15) 0.54991(15) 0.31310(16) 0.0545(4) Uani d . 1 1
H H3 0.3950 0.5302 0.3081 0.065 Uiso calc R 1 1
C C4 0.57071(16) 0.49879(14) 0.22443(16) 0.0523(3) Uani d . 1 1
H H4 0.5185 0.4439 0.1599 0.063 Uiso calc R 1 1
C C5 0.72189(15) 0.52826(12) 0.23035(13) 0.0432(3) Uani d . 1 1
H H5 0.7710 0.4922 0.1709 0.052 Uiso calc R 1 1
C C6 0.80051(12) 0.61176(10) 0.32501(11) 0.0321(2) Uani d . 1 1
C C7 1.05883(13) 0.68706(11) 0.43826(12) 0.0365(2) Uani d . 1 1
C C8 1.00619(14) 0.69227(13) 0.56496(12) 0.0400(3) Uani d . 1 1
H H8A 1.0811 0.7365 0.6327 0.048 Uiso calc R 1 1
H H8B 0.9981 0.6096 0.5974 0.048 Uiso calc R 1 1
C C9 1.00187(16) 0.64258(13) 0.20101(12) 0.0430(3) Uani d . 1 1
H H9A 0.9145 0.6591 0.1264 0.052 Uiso calc R 1 1
H H9B 1.0779 0.7059 0.2021 0.052 Uiso calc R 1 1
C C10 1.06719(14) 0.52290(14) 0.18089(12) 0.0430(3) Uani d . 1 1
N N1 0.95243(11) 0.64883(9) 0.32600(9) 0.0343(2) Uani d . 1 1
C C11 1.12110(16) 0.42755(16) 0.16435(14) 0.0528(3) Uani d . 1 1
H H11 1.1637 0.3522 0.1513 0.063 Uiso calc R 1 1
O O1 1.18902(11) 0.71561(11) 0.43539(11) 0.0552(3) Uani d . 1 1
S S1 0.82271(4) 0.76777(3) 0.53643(3) 0.04266(12) Uani d . 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 119.60(12)
C2 C1 S1 120.43(10)
C6 C1 S1 119.97(9)
C3 C2 C1 120.88(13)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 119.52(12)
C2 C3 H3 120.2
C4 C3 H3 120.2
C3 C4 C5 120.71(13)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 120.20(12)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 119.07(11)
C5 C6 N1 120.54(10)
C1 C6 N1 120.34(10)
O1 C7 N1 121.86(11)
O1 C7 C8 121.83(12)
N1 C7 C8 116.32(10)
C7 C8 S1 110.60(9)
C7 C8 H8A 109.5
S1 C8 H8A 109.5
C7 C8 H8B 109.5
S1 C8 H8B 109.5
H8A C8 H8B 108.1
C10 C9 N1 112.76(10)
C10 C9 H9A 109.0
N1 C9 H9A 109.0
C10 C9 H9B 109.0
N1 C9 H9B 109.0
H9A C9 H9B 107.8
C11 C10 C9 179.18(14)
C7 N1 C6 123.91(9)
C7 N1 C9 117.17(10)
C6 N1 C9 118.89(10)
C10 C11 H11 180.0
C1 S1 C8 95.14(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3924(17)
C1 C6 1.3990(16)
C1 S1 1.7542(13)
C2 C3 1.374(2)
C2 H2 0.9300
C3 C4 1.379(2)
C3 H3 0.9300
C4 C5 1.385(2)
C4 H4 0.9300
C5 C6 1.3919(17)
C5 H5 0.9300
C6 N1 1.4239(14)
C7 O1 1.2204(15)
C7 N1 1.3709(16)
C7 C8 1.5023(16)
C8 S1 1.8021(13)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.4660(19)
C9 N1 1.4707(14)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.177(2)
C11 H11 0.9300
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
C11 H11 O1 2_745 0.93 2.32 3.1937(19) 156.9
