#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/34/2233426.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_2233426
loop_
_publ_author_name
'Wang, Zhiming'
'Yu, Bin'
'Zhang, Xiuqin'
'Cui, Yuan'
'Sun, Xiaoqiang'
_publ_section_title
;
 3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one
;
_journal_coeditor_code           DS2160
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o390
_journal_paper_doi               10.1107/S1600536811054948
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H7 F N2 O S'
_chemical_formula_moiety         'C14 H7 F N2 O S'
_chemical_formula_sum            'C14 H7 F N2 O S'
_chemical_formula_weight         270.28
_chemical_name_systematic
;
3-Fluoro-12H-benzimidazo[2,1-b][1,3]benzothiazin-12-one
;
_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                 94.375(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5027(12)
_cell_length_b                   7.0759(9)
_cell_length_c                   16.931(2)
_cell_measurement_reflns_used    3848
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.79
_cell_measurement_theta_min      2.41
_cell_volume                     1135.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5987
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.9444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0359
_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)+(0.0611P)²+0.4006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1062
_reflns_number_gt                1772
_reflns_number_total             1989
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ds2160.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233426
_cod_database_fobs_code          2233426
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_symmetry_multiplicity
S S1 -0.14487(5) 0.16939(8) 0.36622(3) 0.0538(2) Uani d . 1 1
F F1 -0.43167(13) 0.1082(2) 0.59933(8) 0.0691(4) Uani d . 1 1
O O1 0.19345(15) 0.3338(2) 0.54945(8) 0.0550(4) Uani d . 1 1
N N1 0.08266(18) 0.2319(2) 0.28889(9) 0.0512(4) Uani d . 1 1
N N2 0.12490(15) 0.2778(2) 0.42060(8) 0.0386(3) Uani d . 1 1
C C1 0.4856(2) 0.4053(3) 0.36667(13) 0.0549(5) Uani d . 1 1
H H1 0.5742 0.4478 0.3860 0.066 Uiso calc R 1 1
C C2 0.3838(2) 0.3749(3) 0.41907(12) 0.0478(4) Uani d . 1 1
H H2 0.4024 0.3929 0.4733 0.057 Uiso calc R 1 1
C C3 0.2520(2) 0.3161(2) 0.38695(11) 0.0409(4) Uani d . 1 1
C C4 0.2239(2) 0.2870(3) 0.30570(11) 0.0458(4) Uani d . 1 1
C C5 0.3284(2) 0.3134(3) 0.25403(12) 0.0570(5) Uani d . 1 1
H H5 0.3112 0.2914 0.2000 0.068 Uiso calc R 1 1
C C6 0.4596(2) 0.3741(3) 0.28586(13) 0.0600(5) Uani d . 1 1
H H6 0.5314 0.3942 0.2525 0.072 Uiso calc R 1 1
C C7 0.0288(2) 0.2291(2) 0.35679(10) 0.0429(4) Uani d . 1 1
C C8 0.0987(2) 0.2875(2) 0.50112(10) 0.0404(4) Uani d . 1 1
C C9 -0.04393(18) 0.2395(2) 0.52280(10) 0.0387(4) Uani d . 1 1
C C10 -0.1557(2) 0.1855(2) 0.46872(11) 0.0420(4) Uani d . 1 1
C C11 -0.2867(2) 0.1387(3) 0.49526(12) 0.0474(5) Uani d . 1 1
H H11 -0.3609 0.0999 0.4599 0.057 Uiso calc R 1 1
C C12 -0.3033(2) 0.1512(3) 0.57463(12) 0.0496(5) Uani d . 1 1
C C13 -0.1972(2) 0.2037(3) 0.62965(12) 0.0517(5) Uani d . 1 1
H H13 -0.2121 0.2090 0.6833 0.062 Uiso calc R 1 1
C C14 -0.0687(2) 0.2480(3) 0.60323(11) 0.0446(4) Uani d . 1 1
H H14 0.0043 0.2848 0.6397 0.054 Uiso calc R 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'
F F 0.0171 0.0103 '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
C7 S1 C10 101.85(9)
C7 N1 C4 105.11(16)
C3 N2 C7 105.38(14)
C3 N2 C8 127.34(15)
C7 N2 C8 127.28(15)
C2 C1 C6 121.9(2)
C2 C1 H1 119.1
C6 C1 H1 119.1
C1 C2 C3 116.76(19)
C1 C2 H2 121.6
C3 C2 H2 121.6
C2 C3 C4 121.90(18)
C2 C3 N2 132.68(17)
C4 C3 N2 105.41(16)
C5 C4 C3 120.66(19)
C5 C4 N1 128.96(19)
C3 C4 N1 110.38(17)
C4 C5 C6 117.5(2)
C4 C5 H5 121.2
C6 C5 H5 121.2
C5 C6 C1 121.2(2)
C5 C6 H6 119.4
C1 C6 H6 119.4
N1 C7 N2 113.71(17)
N1 C7 S1 122.20(14)
N2 C7 S1 124.09(14)
O1 C8 N2 119.32(17)
O1 C8 C9 122.96(16)
N2 C8 C9 117.72(15)
C10 C9 C14 118.16(17)
C10 C9 C8 124.53(16)
C14 C9 C8 117.31(16)
C11 C10 C9 120.31(17)
C11 C10 S1 115.18(14)
C9 C10 S1 124.51(15)
C12 C11 C10 118.25(18)
C12 C11 H11 120.9
C10 C11 H11 120.9
F1 C12 C13 118.95(18)
F1 C12 C11 117.57(18)
C13 C12 C11 123.47(19)
C12 C13 C14 117.93(19)
C12 C13 H13 121.0
C14 C13 H13 121.0
C13 C14 C9 121.85(18)
C13 C14 H14 119.1
C9 C14 H14 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.723(2)
S1 C10 1.7501(19)
F1 C12 1.354(2)
O1 C8 1.214(2)
N1 C7 1.294(2)
N1 C4 1.406(3)
N2 C3 1.401(2)
N2 C7 1.403(2)
N2 C8 1.406(2)
C1 C2 1.378(3)
C1 C6 1.389(3)
C1 H1 0.9300
C2 C3 1.390(3)
C2 H2 0.9300
C3 C4 1.397(3)
C4 C5 1.385(3)
C5 C6 1.388(3)
C5 H5 0.9300
C6 H6 0.9300
C8 C9 1.471(3)
C9 C10 1.402(2)
C9 C14 1.401(2)
C10 C11 1.395(3)
C11 C12 1.368(3)
C11 H11 0.9300
C12 C13 1.371(3)
C13 C14 1.369(3)
C13 H13 0.9300
C14 H14 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
_geom_hbond_publ_flag
C14 H14 N1 4_566 0.93 2.58 3.359(2) 141 yes
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
C6 C1 C2 C3 -1.7(3)
C1 C2 C3 C4 0.7(3)
C1 C2 C3 N2 -177.85(18)
C7 N2 C3 C2 178.39(19)
C8 N2 C3 C2 -1.1(3)
C7 N2 C3 C4 -0.31(18)
C8 N2 C3 C4 -179.83(15)
C2 C3 C4 C5 1.0(3)
N2 C3 C4 C5 179.83(16)
C2 C3 C4 N1 -178.82(16)
N2 C3 C4 N1 0.06(19)
C7 N1 C4 C5 -179.51(19)
C7 N1 C4 C3 0.2(2)
C3 C4 C5 C6 -1.6(3)
N1 C4 C5 C6 178.15(19)
C4 C5 C6 C1 0.6(3)
C2 C1 C6 C5 1.0(3)
C4 N1 C7 N2 -0.5(2)
C4 N1 C7 S1 179.82(13)
C3 N2 C7 N1 0.5(2)
C8 N2 C7 N1 -179.97(16)
C3 N2 C7 S1 -179.78(13)
C8 N2 C7 S1 -0.3(2)
C10 S1 C7 N1 178.93(15)
C10 S1 C7 N2 -0.75(17)
C3 N2 C8 O1 0.0(3)
C7 N2 C8 O1 -179.37(17)
C3 N2 C8 C9 -179.66(15)
C7 N2 C8 C9 0.9(2)
O1 C8 C9 C10 180.00(17)
N2 C8 C9 C10 -0.3(2)
O1 C8 C9 C14 -0.2(3)
N2 C8 C9 C14 179.46(15)
C14 C9 C10 C11 -1.1(2)
C8 C9 C10 C11 178.63(16)
C14 C9 C10 S1 179.32(13)
C8 C9 C10 S1 -0.9(2)
C7 S1 C10 C11 -178.27(13)
C7 S1 C10 C9 1.29(17)
C9 C10 C11 C12 1.5(3)
S1 C10 C11 C12 -178.94(14)
C10 C11 C12 F1 178.98(16)
C10 C11 C12 C13 -1.4(3)
F1 C12 C13 C14 -179.48(17)
C11 C12 C13 C14 0.9(3)
C12 C13 C14 C9 -0.5(3)
C10 C9 C14 C13 0.6(3)
C8 C9 C14 C13 -179.15(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657397
