#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229248.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_2229248
loop_
_publ_author_name
'Dawe, Louise N.'
'Ahmed, Abeer'
'Daneshtalab, Mohsen'
_publ_section_title
;
 4-Oxo-1,4-dihydrobenzo[h][1,3]thiazeto[3,2-a]quinoline-1,3-dicarboxylic
 acid
;
_journal_coeditor_code           SU2249
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o529
_journal_paper_doi               10.1107/S1600536811003333
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H9 N O5 S'
_chemical_formula_moiety         'C16 H9 N O5 S'
_chemical_formula_sum            'C16 H9 N O5 S'
_chemical_formula_weight         327.31
_chemical_name_systematic
;
4-Oxo-1,4-dihydrobenzo[h][1,3]thiazeto[3,2-a]quinoline-1,3-
dicarboxylic acid
;
_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                 106.081(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.237(2)
_cell_length_b                   16.171(5)
_cell_length_c                   11.929(4)
_cell_measurement_reflns_used    4915
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.5769
_cell_measurement_theta_min      2.1779
_cell_volume                     1341.4(7)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    '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      153(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'graphite - Rigaku SHINE'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17300
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1999)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.295
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0875
_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)+(0.0366P)²+2.1946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                2614
_reflns_number_total             2769
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2249.cif
_cod_data_source_block           I
_cod_original_cell_volume        1341.5(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229248
_cod_database_fobs_code          2229248
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_disorder_assembly
_atom_site_disorder_group
S S1 0.60834(14) 0.26465(6) 0.14885(8) 0.0347(3) Uani d . 1 . .
O O1 0.5029(4) -0.01520(17) 0.3384(2) 0.0387(7) Uani d . 1 . .
O O2 0.2537(4) 0.33079(19) -0.0999(3) 0.0512(8) Uani d . 1 . .
O O3 0.1270(4) 0.25356(17) 0.0178(2) 0.0370(6) Uani d D 1 . .
O O4 0.7870(4) 0.20609(17) 0.3966(2) 0.0379(7) Uani d . 1 . .
O O5 0.7226(4) 0.08587(19) 0.4695(2) 0.0439(7) Uani d D 1 . .
N N1 0.4277(4) 0.14703(17) 0.0711(2) 0.0257(6) Uani d . 1 . .
C C1 0.5397(5) 0.1656(2) 0.1790(3) 0.0274(7) Uani d . 1 . .
C C2 0.5731(5) 0.1139(2) 0.2722(3) 0.0289(8) Uani d . 1 . .
C C3 0.4829(5) 0.0354(2) 0.2544(3) 0.0303(8) Uani d . 1 . .
C C4 0.3696(5) 0.0139(2) 0.1369(3) 0.0277(8) Uani d . 1 . .
C C5 0.2892(5) -0.0668(2) 0.1153(3) 0.0318(8) Uani d . 1 . .
H H5 0.3105 -0.1057 0.1774 0.038 Uiso calc R 1 . .
C C6 0.1828(5) -0.0887(2) 0.0074(3) 0.0317(8) Uani d . 1 . .
H H6 0.1297 -0.1428 -0.0048 0.038 Uiso calc R 1 . .
C C7 0.1484(5) -0.0329(2) -0.0882(3) 0.0281(8) Uani d . 1 . .
C C8 0.0343(5) -0.0566(2) -0.2002(3) 0.0327(8) Uani d . 1 . .
H H8 -0.0180 -0.1108 -0.2118 0.039 Uiso calc R 1 . .
C C9 -0.0019(5) -0.0027(3) -0.2920(3) 0.0364(9) Uani d . 1 . .
H H9 -0.0819 -0.0190 -0.3661 0.044 Uiso calc R 1 . .
C C10 0.0790(6) 0.0762(2) -0.2765(3) 0.0359(9) Uani d . 1 . .
H H10 0.0552 0.1130 -0.3410 0.043 Uiso calc R 1 . .
C C11 0.1927(5) 0.1015(2) -0.1696(3) 0.0324(8) Uani d . 1 . .
H H11 0.2475 0.1553 -0.1611 0.039 Uiso calc R 1 . .
C C12 0.2288(5) 0.0480(2) -0.0719(3) 0.0275(8) Uani d . 1 . .
C C13 0.3401(5) 0.0702(2) 0.0439(3) 0.0254(7) Uani d . 1 . .
C C14 0.4427(5) 0.2249(2) 0.0104(3) 0.0298(8) Uani d . 1 . .
H H14 0.5090 0.2174 -0.0521 0.036 Uiso calc R 1 . .
C C15 0.2618(5) 0.2759(2) -0.0304(3) 0.0327(8) Uani d . 1 . .
C C16 0.7025(5) 0.1379(2) 0.3852(3) 0.0332(9) Uani d . 1 . .
H H5A 0.649(6) 0.039(2) 0.432(4) 0.052 Uiso d D 1 . .
H H3 0.008(4) 0.277(2) -0.029(3) 0.044 Uiso d 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
C1 S1 C14 . . 73.49(16) ?
C15 O3 H3 . . 107(3) ?
C16 O5 H5A . . 103(3) ?
C1 N1 C13 . . 122.3(3) ?
C1 N1 C14 . . 99.9(3) ?
C13 N1 C14 . . 137.7(3) ?
N1 C1 C2 . . 124.6(3) ?
N1 C1 S1 . . 97.9(2) ?
C2 C1 S1 . . 137.5(3) ?
C1 C2 C3 . . 117.2(3) ?
C1 C2 C16 . . 121.0(3) ?
C3 C2 C16 . . 121.8(3) ?
O1 C3 C2 . . 120.8(3) ?
O1 C3 C4 . . 121.0(3) ?
C2 C3 C4 . . 118.2(3) ?
C13 C4 C5 . . 119.1(3) ?
C13 C4 C3 . . 121.8(3) ?
C5 C4 C3 . . 119.1(3) ?
C6 C5 C4 . . 120.6(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C7 . . 121.7(3) ?
C5 C6 H6 . . 119.2 ?
C7 C6 H6 . . 119.2 ?
C8 C7 C6 . . 120.8(3) ?
C8 C7 C12 . . 119.2(3) ?
C6 C7 C12 . . 120.0(3) ?
C9 C8 C7 . . 121.0(4) ?
C9 C8 H8 . . 119.5 ?
C7 C8 H8 . . 119.5 ?
C8 C9 C10 . . 119.8(3) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C11 C10 C9 . . 121.1(4) ?
C11 C10 H10 . . 119.5 ?
C9 C10 H10 . . 119.5 ?
C10 C11 C12 . . 120.5(3) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C7 . . 118.3(3) ?
C11 C12 C13 . . 124.3(3) ?
C7 C12 C13 . . 117.3(3) ?
N1 C13 C4 . . 115.7(3) ?
N1 C13 C12 . . 123.0(3) ?
C4 C13 C12 . . 121.3(3) ?
N1 C14 C15 . . 116.8(3) ?
N1 C14 S1 . . 88.6(2) ?
C15 C14 S1 . . 112.6(3) ?
N1 C14 H14 . . 112.3 ?
C15 C14 H14 . . 112.3 ?
S1 C14 H14 . . 112.3 ?
O2 C15 O3 . . 127.1(4) ?
O2 C15 C14 . . 119.8(4) ?
O3 C15 C14 . . 113.1(3) ?
O4 C16 O5 . . 123.0(3) ?
O4 C16 C2 . . 120.2(3) ?
O5 C16 C2 . . 116.8(4) ?
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 C1 . 1.744(4) ?
S1 C14 . 1.866(4) ?
O1 C3 . 1.271(4) ?
O2 C15 . 1.205(4) ?
O3 C15 . 1.314(5) ?
O3 H3 . 0.963(19) ?
O4 C16 . 1.250(5) ?
O5 C16 . 1.288(5) ?
O5 H5A . 0.965(19) ?
N1 C1 . 1.350(4) ?
N1 C13 . 1.392(4) ?
N1 C14 . 1.472(4) ?
C1 C2 . 1.358(5) ?
C2 C3 . 1.416(5) ?
C2 C16 . 1.464(5) ?
C3 C4 . 1.456(5) ?
C4 C13 . 1.406(5) ?
C4 C5 . 1.423(5) ?
C5 C6 . 1.351(5) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.421(5) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.416(5) ?
C7 C12 . 1.423(5) ?
C8 C9 . 1.366(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.394(6) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.375(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.416(5) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.438(5) ?
C14 C15 . 1.509(5) ?
C14 H14 . 1.0000 ?
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
O5 H5A O1 . 0.96(4) 1.57(4) 2.504(4) 161(4) y
O3 H3 O4 4_465 0.97(3) 1.62(3) 2.569(4) 166(3) y
