#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/86/2228629.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228629
loop_
_publ_author_name
'al-Rashida, Mariya'
'Nagra, Saeed Ahmad'
'Khan, Islam Ullah'
'Kostakis, George'
'Abbas, Ghulam'
_publ_section_title
;
 3-(6-Bromo-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dione
;
_journal_coeditor_code           ZQ2069
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3081
_journal_page_last               o3082
_journal_paper_doi               10.1107/S1600536810044648
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H11 Br N2 O4 S'
_chemical_formula_moiety         'C16 H11 Br N2 O4 S'
_chemical_formula_sum            'C16 H11 Br N2 O4 S'
_chemical_formula_weight         407.24
_chemical_name_systematic
;
3-(6-Bromo-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-
benzothiadiazine-1,1-dione
;
_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                 94.607(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0778(4)
_cell_length_b                   8.6070(6)
_cell_length_c                   25.6290(16)
_cell_measurement_reflns_used    2932
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.05
_cell_measurement_theta_min      3.06
_cell_volume                     1556.24(17)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et
al., 2006)
;
_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 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            17309
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    2.800
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2007)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.509
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3873
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0423P)²+0.1442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                1969
_reflns_number_total             3873
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zq2069.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228629
_cod_database_fobs_code          2228629
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_disorder_assembly
_atom_site_disorder_group
S S1 1.22103(10) 0.73566(10) 0.31055(3) 0.0337(2) Uani d . 1 . .
O O2 1.2394(3) 0.5717(3) 0.30708(9) 0.0463(6) Uani d . 1 . .
O O3 1.3885(3) 0.8294(3) 0.31425(9) 0.0465(6) Uani d . 1 . .
N N2 1.0884(3) 0.7953(3) 0.25943(10) 0.0287(6) Uani d D 1 . .
H H2A 1.085(4) 0.893(3) 0.2592(12) 0.034 Uiso d D 1 . .
N N4 0.8018(3) 0.7790(4) 0.30189(10) 0.0371(7) Uani d D 1 . .
H H4A 0.690(4) 0.780(4) 0.3005(13) 0.045 Uiso d D 1 . .
Br Br1 -0.00741(5) 0.67254(5) 0.060030(16) 0.06277(19) Uani d . 1 . .
C C5 0.3194(4) 0.7029(4) 0.13029(13) 0.0350(8) Uani d . 1 . .
H H5 0.2622 0.6278 0.1498 0.042 Uiso calc R 1 . .
C C6 0.2305(5) 0.7577(4) 0.08503(13) 0.0403(9) Uani d . 1 . .
C C7 0.3086(5) 0.8725(4) 0.05590(14) 0.0455(9) Uani d . 1 . .
H H7 0.2429 0.9099 0.0256 0.055 Uiso calc R 1 . .
C C8 0.4824(5) 0.9304(4) 0.07182(13) 0.0424(9) Uani d . 1 . .
H H8 0.5374 1.0068 0.0523 0.051 Uiso calc R 1 . .
C C9 0.5766(4) 0.8743(4) 0.11749(12) 0.0324(8) Uani d . 1 . .
O O1 0.7509(3) 0.9378(3) 0.13110(8) 0.0398(6) Uani d . 1 . .
C C10 0.4984(4) 0.7614(4) 0.14695(12) 0.0287(7) Uani d . 1 . .
C C4 0.6000(4) 0.7086(4) 0.19593(12) 0.0286(8) Uani d . 1 . .
O O4 0.5369(3) 0.6116(3) 0.22456(9) 0.0395(6) Uani d . 1 . .
C C3 0.7845(4) 0.7819(4) 0.20758(12) 0.0272(7) Uani d . 1 . .
C C2 0.8469(4) 0.8871(4) 0.17524(12) 0.0347(8) Uani d . 1 . .
H H2 0.9665 0.9291 0.1838 0.042 Uiso calc R 1 . .
C C11 0.8977(4) 0.7310(4) 0.25680(12) 0.0289(7) Uani d . 1 . .
H H11 0.9066 0.6174 0.2568 0.035 Uiso calc R 1 . .
C C12 0.8888(4) 0.7966(4) 0.35104(12) 0.0295(8) Uani d . 1 . .
C C13 0.7836(4) 0.8366(4) 0.39290(13) 0.0372(8) Uani d . 1 . .
H H13 0.6531 0.8494 0.3871 0.045 Uiso calc R 1 . .
C C14 0.8682(5) 0.8573(4) 0.44190(14) 0.0431(9) Uani d . 1 . .
H H14 0.7942 0.8825 0.4691 0.052 Uiso calc R 1 . .
C C16 1.1691(5) 0.8056(4) 0.41215(13) 0.0402(9) Uani d . 1 . .
H H16 1.2999 0.7964 0.4183 0.048 Uiso calc R 1 . .
C C15 1.0631(5) 0.8417(4) 0.45229(14) 0.0445(9) Uani d . 1 . .
H H15 1.1196 0.8557 0.4860 0.053 Uiso calc R 1 . .
C C17 1.0843(4) 0.7823(4) 0.36172(12) 0.0291(8) 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 0.0033 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'
Br Br -0.2901 2.4595 '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
O2 S1 O3 . . 119.01(14) ?
O2 S1 N2 . . 108.16(14) ?
O3 S1 N2 . . 107.20(14) ?
O2 S1 C17 . . 109.63(15) ?
O3 S1 C17 . . 109.16(14) ?
N2 S1 C17 . . 102.36(14) ?
C11 N2 S1 . . 112.9(2) ?
C11 N2 H2A . . 111(2) ?
S1 N2 H2A . . 109(2) ?
C12 N4 C11 . . 124.3(2) ?
C12 N4 H4A . . 115(3) ?
C11 N4 H4A . . 120(3) ?
C6 C5 C10 . . 118.8(3) ?
C6 C5 H5 . . 120.6 ?
C10 C5 H5 . . 120.6 ?
C5 C6 C7 . . 122.2(3) ?
C5 C6 Br1 . . 119.4(3) ?
C7 C6 Br1 . . 118.5(2) ?
C8 C7 C6 . . 119.5(3) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C9 . . 119.2(3) ?
C7 C8 H8 . . 120.4 ?
C9 C8 H8 . . 120.4 ?
O1 C9 C10 . . 122.5(3) ?
O1 C9 C8 . . 116.0(3) ?
C10 C9 C8 . . 121.5(3) ?
C2 O1 C9 . . 118.0(2) ?
C9 C10 C5 . . 118.8(3) ?
C9 C10 C4 . . 119.8(3) ?
C5 C10 C4 . . 121.3(3) ?
O4 C4 C3 . . 122.5(3) ?
O4 C4 C10 . . 123.3(3) ?
C3 C4 C10 . . 114.2(3) ?
C2 C3 C4 . . 120.3(3) ?
C2 C3 C11 . . 122.8(3) ?
C4 C3 C11 . . 117.0(3) ?
C3 C2 O1 . . 125.2(3) ?
C3 C2 H2 . . 117.4 ?
O1 C2 H2 . . 117.4 ?
N4 C11 N2 . . 110.3(2) ?
N4 C11 C3 . . 109.6(2) ?
N2 C11 C3 . . 111.0(3) ?
N4 C11 H11 . . 108.6 ?
N2 C11 H11 . . 108.6 ?
C3 C11 H11 . . 108.6 ?
N4 C12 C13 . . 120.5(3) ?
N4 C12 C17 . . 122.6(3) ?
C13 C12 C17 . . 116.9(3) ?
C14 C13 C12 . . 121.3(3) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C13 C14 C15 . . 121.4(3) ?
C13 C14 H14 . . 119.3 ?
C15 C14 H14 . . 119.3 ?
C15 C16 C17 . . 120.8(3) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C16 C15 C14 . . 118.5(3) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C16 C17 C12 . . 121.0(3) ?
C16 C17 S1 . . 120.5(2) ?
C12 C17 S1 . . 118.4(2) ?
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 O2 . 1.421(2) ?
S1 O3 . 1.431(2) ?
S1 N2 . 1.632(3) ?
S1 C17 . 1.738(3) ?
N2 C11 . 1.456(4) ?
N2 H2A . 0.84(2) ?
N4 C12 . 1.365(4) ?
N4 C11 . 1.446(4) ?
N4 H4A . 0.79(3) ?
Br1 C6 . 1.900(3) ?
C5 C6 . 1.359(4) ?
C5 C10 . 1.398(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.380(5) ?
C7 C8 . 1.359(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.387(4) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.368(4) ?
C9 C10 . 1.375(4) ?
O1 C2 . 1.345(4) ?
C10 C4 . 1.468(4) ?
C4 O4 . 1.219(3) ?
C4 C3 . 1.459(4) ?
C3 C2 . 1.327(4) ?
C3 C11 . 1.504(4) ?
C2 H2 . 0.9300 ?
C11 H11 . 0.9800 ?
C12 C13 . 1.398(4) ?
C12 C17 . 1.394(4) ?
C13 C14 . 1.359(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.391(5) ?
C14 H14 . 0.9300 ?
C16 C15 . 1.357(5) ?
C16 C17 . 1.395(4) ?
C16 H16 . 0.9300 ?
C15 H15 . 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
N4 H4A O4 . 0.79(3) 2.59(3) 2.987(3) 113(3) yes
N4 H4A O3 1_455 0.79(3) 2.23(3) 2.999(3) 164(3) yes
C13 H13 O3 1_455 0.9300 2.542(2) 3.314(4) 140.6(2) yes
N2 H2A O2 . 0.84(2) 2.67(3) 3.222(4) 124(2) yes
C2 H2 O2 . 0.9300 2.412(2) 3.330(4) 169.3(2) yes
N2 H2A O4 . 0.84(2) 2.12(3) 2.903(4) 154(3) 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
O2 S1 N2 C11 . . . . 61.9(2) ?
O3 S1 N2 C11 . . . . -168.6(2) ?
C17 S1 N2 C11 . . . . -53.8(2) ?
C10 C5 C6 C7 . . . . -2.0(5) ?
C10 C5 C6 Br1 . . . . 177.0(2) ?
C5 C6 C7 C8 . . . . 1.9(5) ?
Br1 C6 C7 C8 . . . . -177.2(3) ?
C6 C7 C8 C9 . . . . -0.9(5) ?
C7 C8 C9 O1 . . . . 179.9(3) ?
C7 C8 C9 C10 . . . . 0.1(5) ?
C10 C9 O1 C2 . . . . -0.4(4) ?
C8 C9 O1 C2 . . . . 179.7(3) ?
O1 C9 C10 C5 . . . . 179.9(3) ?
C8 C9 C10 C5 . . . . -0.2(5) ?
O1 C9 C10 C4 . . . . 2.1(5) ?
C8 C9 C10 C4 . . . . -178.0(3) ?
C6 C5 C10 C9 . . . . 1.2(5) ?
C6 C5 C10 C4 . . . . 179.0(3) ?
C9 C10 C4 O4 . . . . 178.2(3) ?
C5 C10 C4 O4 . . . . 0.5(5) ?
C9 C10 C4 C3 . . . . -2.0(4) ?
C5 C10 C4 C3 . . . . -179.7(3) ?
O4 C4 C3 C2 . . . . -179.9(3) ?
C10 C4 C3 C2 . . . . 0.3(4) ?
O4 C4 C3 C11 . . . . 0.8(4) ?
C10 C4 C3 C11 . . . . -179.0(3) ?
C4 C3 C2 O1 . . . . 1.4(5) ?
C11 C3 C2 O1 . . . . -179.3(3) ?
C9 O1 C2 C3 . . . . -1.5(5) ?
C12 N4 C11 N2 . . . . -35.8(4) ?
C12 N4 C11 C3 . . . . -158.3(3) ?
S1 N2 C11 N4 . . . . 61.6(3) ?
S1 N2 C11 C3 . . . . -176.8(2) ?
C2 C3 C11 N4 . . . . 114.2(3) ?
C4 C3 C11 N4 . . . . -66.5(3) ?
C2 C3 C11 N2 . . . . -7.9(4) ?
C4 C3 C11 N2 . . . . 171.4(2) ?
C11 N4 C12 C13 . . . . -177.1(3) ?
C11 N4 C12 C17 . . . . 5.6(5) ?
N4 C12 C13 C14 . . . . -178.8(3) ?
C17 C12 C13 C14 . . . . -1.4(5) ?
C12 C13 C14 C15 . . . . 0.9(5) ?
C17 C16 C15 C14 . . . . -1.0(5) ?
C13 C14 C15 C16 . . . . 0.3(5) ?
C15 C16 C17 C12 . . . . 0.5(5) ?
C15 C16 C17 S1 . . . . -179.9(3) ?
N4 C12 C17 C16 . . . . 178.0(3) ?
C13 C12 C17 C16 . . . . 0.6(5) ?
N4 C12 C17 S1 . . . . -1.6(4) ?
C13 C12 C17 S1 . . . . -179.0(2) ?
O2 S1 C17 C16 . . . . 89.7(3) ?
O3 S1 C17 C16 . . . . -42.3(3) ?
N2 S1 C17 C16 . . . . -155.7(3) ?
O2 S1 C17 C12 . . . . -90.7(3) ?
O3 S1 C17 C12 . . . . 137.3(3) ?
N2 S1 C17 C12 . . . . 24.0(3) ?
