#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226334.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_2226334
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Rosli, Mohd Mustaqim'
'Gowda, Janardhana'
'Khader, A. M. A.'
'Kalluraya, B.'
_publ_section_title
;
 4-(1H-Benzimidazol-2-ylmethyl)-2H-1,4-benzothiazin-3(4H)-one
;
_journal_coeditor_code           WN2387
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1495
_journal_paper_doi               10.1107/S1600536810019367
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H13 N3 O S'
_chemical_formula_moiety         'C16 H13 N3 O S'
_chemical_formula_sum            'C16 H13 N3 O S'
_chemical_formula_weight         295.35
_chemical_name_systematic
4-(1H-Benzimidazol-2-ylmethyl)-2H-1,4-benzothiazin-3(4H)-one
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4498(8)
_cell_length_b                   17.0223(16)
_cell_length_c                   17.4454(16)
_cell_measurement_reflns_used    4703
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      31.59
_cell_measurement_theta_min      2.39
_cell_volume                     2806.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector diffractometer
;
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16727
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.8926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0409
_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)+(0.0605P)²+1.2202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                3185
_reflns_number_total             4075
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2387.cif
_cod_data_source_block           I
_cod_database_code               2226334
_cod_database_fobs_code          2226334
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 0.69098(4) 0.04490(2) 0.49857(2) 0.02567(12) Uani d . 1 . .
O O1 0.90053(12) -0.12536(7) 0.41611(7) 0.0283(2) Uani d . 1 . .
N N1 1.05774(11) -0.12424(7) 0.21967(7) 0.0169(2) Uani d . 1 . .
N N2 0.82471(11) -0.10176(7) 0.21708(7) 0.0166(2) Uani d . 1 . .
N N3 0.84628(12) -0.01064(7) 0.35843(7) 0.0180(2) Uani d . 1 . .
C C1 0.75457(14) 0.05425(8) 0.34596(8) 0.0177(3) Uani d . 1 . .
C C2 0.74342(15) 0.08809(8) 0.27346(8) 0.0210(3) Uani d . 1 . .
H H2A 0.7935 0.0668 0.2325 0.025 Uiso calc R 1 . .
C C3 0.65796(16) 0.15354(9) 0.26189(9) 0.0251(3) Uani d . 1 . .
H H3A 0.6530 0.1764 0.2135 0.030 Uiso calc R 1 . .
C C4 0.58032(16) 0.18488(9) 0.32169(10) 0.0275(3) Uani d . 1 . .
H H4A 0.5232 0.2286 0.3137 0.033 Uiso calc R 1 . .
C C5 0.58816(16) 0.15078(9) 0.39359(10) 0.0256(3) Uani d . 1 . .
H H5A 0.5346 0.1711 0.4337 0.031 Uiso calc R 1 . .
C C6 0.67593(15) 0.08616(8) 0.40635(8) 0.0206(3) Uani d . 1 . .
C C7 0.70051(17) -0.05535(9) 0.46596(9) 0.0261(3) Uani d . 1 . .
H H7A 0.7100 -0.0900 0.5098 0.031 Uiso calc R 1 . .
H H7B 0.6134 -0.0688 0.4396 0.031 Uiso calc R 1 . .
C C8 0.82425(15) -0.06773(8) 0.41241(8) 0.0209(3) Uani d . 1 . .
C C9 0.96991(14) -0.02207(8) 0.30913(8) 0.0191(3) Uani d . 1 . .
H H9A 1.0499 -0.0374 0.3406 0.023 Uiso calc R 1 . .
H H9B 0.9933 0.0274 0.2847 0.023 Uiso calc R 1 . .
C C10 0.94729(13) -0.08304(8) 0.24863(8) 0.0159(2) Uani d . 1 . .
C C11 1.00375(13) -0.17492(8) 0.16502(8) 0.0165(3) Uani d . 1 . .
C C12 1.06703(15) -0.23109(9) 0.11796(8) 0.0213(3) Uani d . 1 . .
H H12A 1.1636 -0.2415 0.1201 0.026 Uiso calc R 1 . .
C C13 0.97847(17) -0.27045(9) 0.06787(9) 0.0245(3) Uani d . 1 . .
H H13A 1.0162 -0.3086 0.0356 0.029 Uiso calc R 1 . .
C C14 0.83220(16) -0.25414(9) 0.06449(9) 0.0234(3) Uani d . 1 . .
H H14A 0.7765 -0.2809 0.0291 0.028 Uiso calc R 1 . .
C C15 0.76917(15) -0.19954(8) 0.11228(8) 0.0198(3) Uani d . 1 . .
H H15A 0.6724 -0.1898 0.1105 0.024 Uiso calc R 1 . .
C C16 0.85770(13) -0.15965(8) 0.16350(8) 0.0158(2) Uani d . 1 . .
H H1N1 1.143(2) -0.1173(12) 0.2353(12) 0.033(5) Uiso 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'
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
C6 S1 C7 . . 95.35(7) ?
C10 N1 C11 . . 107.20(11) ?
C10 N1 H1N1 . . 122.3(14) ?
C11 N1 H1N1 . . 130.5(14) ?
C10 N2 C16 . . 104.70(11) ?
C8 N3 C1 . . 124.36(12) ?
C8 N3 C9 . . 115.55(12) ?
C1 N3 C9 . . 120.02(11) ?
C2 C1 C6 . . 118.86(13) ?
C2 C1 N3 . . 120.42(12) ?
C6 C1 N3 . . 120.71(13) ?
C3 C2 C1 . . 120.45(14) ?
C3 C2 H2A . . 119.8 ?
C1 C2 H2A . . 119.8 ?
C4 C3 C2 . . 120.52(15) ?
C4 C3 H3A . . 119.7 ?
C2 C3 H3A . . 119.7 ?
C3 C4 C5 . . 119.58(14) ?
C3 C4 H4A . . 120.2 ?
C5 C4 H4A . . 120.2 ?
C4 C5 C6 . . 120.46(14) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
C5 C6 C1 . . 120.11(14) ?
C5 C6 S1 . . 120.53(11) ?
C1 C6 S1 . . 119.35(11) ?
C8 C7 S1 . . 111.46(10) ?
C8 C7 H7A . . 109.3 ?
S1 C7 H7A . . 109.3 ?
C8 C7 H7B . . 109.3 ?
S1 C7 H7B . . 109.3 ?
H7A C7 H7B . . 108.0 ?
O1 C8 N3 . . 121.18(13) ?
O1 C8 C7 . . 122.47(14) ?
N3 C8 C7 . . 116.35(12) ?
N3 C9 C10 . . 113.14(11) ?
N3 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
N3 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
N2 C10 N1 . . 113.27(12) ?
N2 C10 C9 . . 125.91(12) ?
N1 C10 C9 . . 120.81(11) ?
N1 C11 C12 . . 132.45(12) ?
N1 C11 C16 . . 105.08(11) ?
C12 C11 C16 . . 122.47(13) ?
C13 C12 C11 . . 116.39(13) ?
C13 C12 H12A . . 121.8 ?
C11 C12 H12A . . 121.8 ?
C12 C13 C14 . . 121.59(13) ?
C12 C13 H13A . . 119.2 ?
C14 C13 H13A . . 119.2 ?
C15 C14 C13 . . 121.92(14) ?
C15 C14 H14A . . 119.0 ?
C13 C14 H14A . . 119.0 ?
C14 C15 C16 . . 116.96(13) ?
C14 C15 H15A . . 121.5 ?
C16 C15 H15A . . 121.5 ?
N2 C16 C15 . . 129.61(12) ?
N2 C16 C11 . . 109.75(11) ?
C15 C16 C11 . . 120.64(13) ?
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 C6 . 1.7611(16) ?
S1 C7 . 1.8011(16) ?
O1 C8 . 1.2191(18) ?
N1 C10 . 1.3552(16) ?
N1 C11 . 1.3831(17) ?
N1 H1N1 . 0.86(2) ?
N2 C10 . 1.3214(16) ?
N2 C16 . 1.3936(17) ?
N3 C8 . 1.3692(19) ?
N3 C1 . 1.4207(17) ?
N3 C9 . 1.4637(17) ?
C1 C2 . 1.394(2) ?
C1 C6 . 1.3990(19) ?
C2 C3 . 1.391(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.382(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.384(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.396(2) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.511(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 C10 . 1.4955(19) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C11 C12 . 1.3950(19) ?
C11 C16 . 1.4046(18) ?
C12 C13 . 1.383(2) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.411(2) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.383(2) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.3998(19) ?
C15 H15A . 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
N1 H1N1 N2 6_656 0.859(19) 1.926(19) 2.7800(15) 173(2) yes
C12 H12A Cg1 4_745 0.93 2.97 3.6736(16) 134 yes
C3 H3A Cg2 7_655 0.93 2.61 3.4750(17) 155 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 N3 C1 C2 . . . . -150.61(14) ?
C9 N3 C1 C2 . . . . 25.96(19) ?
C8 N3 C1 C6 . . . . 30.5(2) ?
C9 N3 C1 C6 . . . . -152.88(13) ?
C6 C1 C2 C3 . . . . 1.4(2) ?
N3 C1 C2 C3 . . . . -177.44(13) ?
C1 C2 C3 C4 . . . . -1.5(2) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C3 C4 C5 C6 . . . . 1.3(2) ?
C4 C5 C6 C1 . . . . -1.4(2) ?
C4 C5 C6 S1 . . . . 177.68(12) ?
C2 C1 C6 C5 . . . . 0.0(2) ?
N3 C1 C6 C5 . . . . 178.85(13) ?
C2 C1 C6 S1 . . . . -179.06(10) ?
N3 C1 C6 S1 . . . . -0.20(18) ?
C7 S1 C6 C5 . . . . 142.33(13) ?
C7 S1 C6 C1 . . . . -38.62(13) ?
C6 S1 C7 C8 . . . . 58.75(12) ?
C1 N3 C8 O1 . . . . 173.88(13) ?
C9 N3 C8 O1 . . . . -2.8(2) ?
C1 N3 C8 C7 . . . . -5.6(2) ?
C9 N3 C8 C7 . . . . 177.65(12) ?
S1 C7 C8 O1 . . . . 137.50(14) ?
S1 C7 C8 N3 . . . . -42.98(17) ?
C8 N3 C9 C10 . . . . 76.17(15) ?
C1 N3 C9 C10 . . . . -100.69(14) ?
C16 N2 C10 N1 . . . . 0.06(15) ?
C16 N2 C10 C9 . . . . 178.82(13) ?
C11 N1 C10 N2 . . . . -0.62(16) ?
C11 N1 C10 C9 . . . . -179.45(12) ?
N3 C9 C10 N2 . . . . 28.7(2) ?
N3 C9 C10 N1 . . . . -152.62(12) ?
C10 N1 C11 C12 . . . . -179.20(15) ?
C10 N1 C11 C16 . . . . 0.88(14) ?
N1 C11 C12 C13 . . . . -178.56(14) ?
C16 C11 C12 C13 . . . . 1.3(2) ?
C11 C12 C13 C14 . . . . 0.3(2) ?
C12 C13 C14 C15 . . . . -1.7(2) ?
C13 C14 C15 C16 . . . . 1.3(2) ?
C10 N2 C16 C15 . . . . -178.42(14) ?
C10 N2 C16 C11 . . . . 0.52(15) ?
C14 C15 C16 N2 . . . . 179.23(13) ?
C14 C15 C16 C11 . . . . 0.4(2) ?
N1 C11 C16 N2 . . . . -0.88(15) ?
C12 C11 C16 N2 . . . . 179.20(12) ?
N1 C11 C16 C15 . . . . 178.18(12) ?
C12 C11 C16 C15 . . . . -1.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745166
