#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/65/2236586.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_2236586
loop_
_publ_author_name
'Narayanan, Ponmudisettu'
'Karthikeyan, Subramani'
'Srinivasan, Panayancheri Coleppa'
'Sethusankar, Krishnan'
_publ_section_title
;
 7H-[1,2]Benzothiazolo[3,2-b]quinazoline 5,5-dioxide
;
_journal_coeditor_code           RK2382
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3082
_journal_paper_doi               10.1107/S1600536812040871
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H10 N2 O2 S'
_chemical_formula_moiety         'C14 H10 N2 O2 S'
_chemical_formula_sum            'C14 H10 N2 O2 S'
_chemical_formula_weight         270.31
_chemical_name_systematic
;
 7H-[1,2]Benzothiazolo[3,2-b]quinazoline 5,5-dioxide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.9389(2)
_cell_length_b                   13.1460(4)
_cell_length_c                   22.7952(7)
_cell_measurement_reflns_used    2328
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.10
_cell_volume                     2379.02(12)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON  (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω-- & φ--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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            21710
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.331
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0336
_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)+(0.0837P)²+0.4043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                1981
_reflns_number_total             2328
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            rk2382.cif
_cod_data_source_block           I
_cod_database_code               2236586
_cod_database_fobs_code          2236586
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_symmetry_multiplicity
C C1 0.0174(2) 0.49618(13) 0.32511(7) 0.0390(4) Uani d . 1 1
C C2 -0.0613(2) 0.51583(15) 0.27215(8) 0.0506(5) Uani d . 1 1
H H2 -0.0732 0.4655 0.2438 0.061 Uiso calc R 1 1
C C3 -0.1217(3) 0.61328(16) 0.26314(9) 0.0556(5) Uani d . 1 1
H H3 -0.1767 0.6288 0.2283 0.067 Uiso calc R 1 1
C C4 -0.1014(2) 0.68776(16) 0.30527(9) 0.0532(5) Uani d . 1 1
H H4 -0.1421 0.7529 0.2981 0.064 Uiso calc R 1 1
C C5 -0.0215(2) 0.66715(14) 0.35795(8) 0.0447(4) Uani d . 1 1
H H5 -0.0084 0.7177 0.3861 0.054 Uiso calc R 1 1
C C6 0.0382(2) 0.56991(12) 0.36773(7) 0.0354(4) Uani d . 1 1
C C7 0.12413(19) 0.53087(11) 0.42037(7) 0.0335(4) Uani d . 1 1
C C8 0.2162(3) 0.36384(13) 0.46019(8) 0.0457(4) Uani d . 1 1
H H8A 0.3027 0.3170 0.4471 0.055 Uiso calc R 1 1
H H8B 0.1206 0.3244 0.4738 0.055 Uiso calc R 1 1
C C9 0.2830(2) 0.42841(13) 0.50934(7) 0.0365(4) Uani d . 1 1
C C10 0.24723(19) 0.53228(12) 0.51127(6) 0.0342(4) Uani d . 1 1
C C11 0.3012(2) 0.58936(14) 0.55898(7) 0.0433(4) Uani d . 1 1
H H11 0.2774 0.6586 0.5605 0.052 Uiso calc R 1 1
C C12 0.3900(2) 0.54436(16) 0.60411(8) 0.0497(5) Uani d . 1 1
H H12 0.4248 0.5832 0.6360 0.060 Uiso calc R 1 1
C C13 0.4270(2) 0.44222(16) 0.60202(8) 0.0498(5) Uani d . 1 1
H H13 0.4872 0.4119 0.6323 0.060 Uiso calc R 1 1
C C14 0.3743(2) 0.38476(13) 0.55469(8) 0.0449(4) Uani d . 1 1
H H14 0.4004 0.3158 0.5532 0.054 Uiso calc R 1 1
N N1 0.1652(2) 0.42909(10) 0.41195(6) 0.0414(4) Uani d . 1 1
N N2 0.15773(18) 0.58305(10) 0.46603(6) 0.0371(3) Uani d . 1 1
O O1 0.24864(17) 0.35324(11) 0.31425(6) 0.0575(4) Uani d . 1 1
O O2 -0.01803(19) 0.30315(10) 0.35705(6) 0.0581(4) Uani d . 1 1
S S1 0.10439(6) 0.38070(3) 0.348166(18) 0.04023(19) 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
C6 C1 C2 122.42(17)
C6 C1 S1 110.51(12)
C2 C1 S1 127.06(14)
C3 C2 C1 117.32(18)
C3 C2 H2 121.3
C1 C2 H2 121.3
C2 C3 C4 120.86(18)
C2 C3 H3 119.6
C4 C3 H3 119.6
C3 C4 C5 121.19(18)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 118.57(17)
C6 C5 H5 120.7
C4 C5 H5 120.7
C1 C6 C5 119.62(15)
C1 C6 C7 112.56(14)
C5 C6 C7 127.81(15)
N2 C7 N1 125.55(14)
N2 C7 C6 125.08(14)
N1 C7 C6 109.36(13)
N1 C8 C9 109.23(14)
N1 C8 H8A 109.8
C9 C8 H8A 109.8
N1 C8 H8B 109.8
C9 C8 H8B 109.8
H8A C8 H8B 108.3
C14 C9 C10 119.20(15)
C14 C9 C8 120.43(16)
C10 C9 C8 120.31(14)
C11 C10 C9 119.36(15)
C11 C10 N2 118.00(14)
C9 C10 N2 122.63(14)
C12 C11 C10 120.64(17)
C12 C11 H11 119.7
C10 C11 H11 119.7
C13 C12 C11 120.12(17)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 119.74(16)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C9 120.93(16)
C13 C14 H14 119.5
C9 C14 H14 119.5
C7 N1 C8 121.96(13)
C7 N1 S1 114.95(11)
C8 N1 S1 121.22(11)
C7 N2 C10 116.43(13)
O2 S1 O1 116.34(9)
O2 S1 N1 110.41(8)
O1 S1 N1 109.76(8)
O2 S1 C1 113.27(9)
O1 S1 C1 111.92(8)
N1 S1 C1 92.60(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.382(2)
C1 C2 1.384(2)
C1 S1 1.7485(18)
C2 C3 1.383(3)
C2 H2 0.9300
C3 C4 1.381(3)
C3 H3 0.9300
C4 C5 1.384(2)
C4 H4 0.9300
C5 C6 1.382(2)
C5 H5 0.9300
C6 C7 1.473(2)
C7 N2 1.275(2)
C7 N1 1.390(2)
C8 N1 1.452(2)
C8 C9 1.502(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C14 1.387(2)
C9 C10 1.395(2)
C10 C11 1.389(2)
C10 N2 1.419(2)
C11 C12 1.380(3)
C11 H11 0.9300
C12 C13 1.375(3)
C12 H12 0.9300
C13 C14 1.382(3)
C13 H13 0.9300
C14 H14 0.9300
N1 S1 1.6589(14)
O1 S1 1.4281(13)
O2 S1 1.4230(13)
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
C2 H2 O1 6_556 0.93 2.43 3.275(2) 150.2
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 -0.7(3)
S1 C1 C2 C3 179.80(15)
C1 C2 C3 C4 0.9(3)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 C6 0.1(3)
C2 C1 C6 C5 0.2(3)
S1 C1 C6 C5 179.80(13)
C2 C1 C6 C7 179.50(15)
S1 C1 C6 C7 -0.94(18)
C4 C5 C6 C1 0.1(3)
C4 C5 C6 C7 -179.04(16)
C1 C6 C7 N2 -179.58(16)
C5 C6 C7 N2 -0.4(3)
C1 C6 C7 N1 1.48(19)
C5 C6 C7 N1 -179.33(16)
N1 C8 C9 C14 -165.40(15)
N1 C8 C9 C10 17.6(2)
C14 C9 C10 C11 -1.1(2)
C8 C9 C10 C11 175.98(16)
C14 C9 C10 N2 178.63(15)
C8 C9 C10 N2 -4.3(2)
C9 C10 C11 C12 0.2(3)
N2 C10 C11 C12 -179.50(15)
C10 C11 C12 C13 0.5(3)
C11 C12 C13 C14 -0.3(3)
C12 C13 C14 C9 -0.6(3)
C10 C9 C14 C13 1.3(3)
C8 C9 C14 C13 -175.78(16)
N2 C7 N1 C8 15.1(3)
C6 C7 N1 C8 -165.98(16)
N2 C7 N1 S1 179.66(14)
C6 C7 N1 S1 -1.41(17)
C9 C8 N1 C7 -22.8(2)
C9 C8 N1 S1 173.54(12)
N1 C7 N2 C10 1.1(2)
C6 C7 N2 C10 -177.62(13)
C11 C10 N2 C7 173.48(15)
C9 C10 N2 C7 -6.2(2)
C7 N1 S1 O2 -115.25(13)
C8 N1 S1 O2 49.45(17)
C7 N1 S1 O1 115.20(13)
C8 N1 S1 O1 -80.10(16)
C7 N1 S1 C1 0.78(14)
C8 N1 S1 C1 165.48(15)
C6 C1 S1 O2 113.68(13)
C2 C1 S1 O2 -66.78(18)
C6 C1 S1 O1 -112.40(13)
C2 C1 S1 O1 67.14(18)
C6 C1 S1 N1 0.13(14)
C2 C1 S1 N1 179.66(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658151
