#------------------------------------------------------------------------------
#$Date: 2015-06-14 05:27:57 +0300 (Sun, 14 Jun 2015) $
#$Revision: 139208 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240840.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_2240840
loop_
_publ_author_name
'Gomes, Ligia R.'
'Low, John Nicolson'
'Cagide, Fernando'
'Borges, Fernanda'
_publ_section_title
;
 Crystal structures of two
 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              766
_journal_page_last               771
_journal_paper_doi               10.1107/S2056989015011044
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H8 N2 O3 S'
_chemical_formula_moiety         'C13 H8 N2 O3 S'
_chemical_formula_sum            'C13 H8 N2 O3 S'
_chemical_formula_weight         272.27
_chemical_name_systematic
;
6-(2-Hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.49(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5563(5)
_cell_length_b                   15.3187(11)
_cell_length_c                   10.1229(7)
_cell_measurement_reflns_used    7040
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1155.72(15)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2006)
;
_computing_publication_material
;
Oscail (McArdle et al.,  2004) and
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
Oscail (McArdle et al.,  2004),
ShelXle (Hübschle et al.,  2011) and
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7713
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.130
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0485P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                2135
_reflns_number_total             2632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7437sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        1155.70(15)
_cod_database_code               2240840
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_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_occupancy
S S1 0.53044(5) 0.47242(3) 0.82245(4) 0.01896(13) Uani d 1
O O5 0.13953(16) 0.30924(7) 0.48703(11) 0.0220(3) Uani d 1
O O62 -0.16684(15) 0.43565(8) 0.04276(11) 0.0244(3) Uani d 1
H H62A -0.1549 0.4787 0.0949 0.037 Uiso d 1
O O67 -0.03352(15) 0.51893(7) 0.25912(11) 0.0202(3) Uani d 1
N N4 0.32960(17) 0.39593(9) 0.62970(12) 0.0153(3) Uani d 1
N N8 0.35861(18) 0.54953(9) 0.59756(13) 0.0182(3) Uani d 1
C C2 0.4957(2) 0.36098(11) 0.83142(15) 0.0200(3) Uani d 1
H H2 0.5482 0.3254 0.9044 0.024 Uiso calc 1
C C3 0.3863(2) 0.33073(11) 0.72355(15) 0.0184(3) Uani d 1
H H3 0.3510 0.2713 0.7121 0.022 Uiso calc 1
C C5 0.2084(2) 0.38137(11) 0.50752(15) 0.0167(3) Uani d 1
C C6 0.1834(2) 0.45847(10) 0.42710(14) 0.0157(3) Uani d 1
C C7 0.2532(2) 0.53721(11) 0.47770(15) 0.0174(3) Uani d 1
H H7 0.2244 0.5873 0.4232 0.021 Uiso calc 1
C C9 0.3934(2) 0.47688(10) 0.66844(15) 0.0159(3) Uani d 1
C C61 0.1006(2) 0.39010(10) 0.19292(14) 0.0162(3) Uani d 1
C C62 -0.0209(2) 0.38331(11) 0.07150(15) 0.0184(3) Uani d 1
C C63 0.0072(2) 0.32092(11) -0.02354(16) 0.0219(4) Uani d 1
H H62 -0.0774 0.3146 -0.1035 0.026 Uiso calc 1
C C64 0.1571(2) 0.26854(11) -0.00138(16) 0.0217(4) Uani d 1
H H64 0.1752 0.2264 -0.0666 0.026 Uiso calc 1
C C65 0.2832(2) 0.27646(11) 0.11565(16) 0.0201(3) Uani d 1
H H65 0.3881 0.2413 0.1289 0.024 Uiso calc 1
C C66 0.2531(2) 0.33623(10) 0.21201(15) 0.0178(3) Uani d 1
H H66 0.3372 0.3409 0.2926 0.021 Uiso calc 1
C C67 0.0738(2) 0.45816(10) 0.29057(15) 0.0160(3) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 S1 C2 90.74(7)
C62 O62 H62A 109.3
C9 N4 C3 113.61(13)
C9 N4 C5 122.40(13)
C3 N4 C5 123.91(13)
C9 N8 C7 113.80(14)
C3 C2 S1 112.14(12)
C3 C2 H2 123.9
S1 C2 H2 123.9
C2 C3 N4 112.72(15)
C2 C3 H3 123.6
N4 C3 H3 123.6
O5 C5 N4 118.75(14)
O5 C5 C6 129.54(14)
N4 C5 C6 111.69(13)
C7 C6 C5 120.26(14)
C7 C6 C67 117.84(14)
C5 C6 C67 121.81(13)
N8 C7 C6 126.02(15)
N8 C7 H7 117.0
C6 C7 H7 117.0
N8 C9 N4 125.30(14)
N8 C9 S1 123.91(12)
N4 C9 S1 110.78(11)
C66 C61 C62 118.53(14)
C66 C61 C67 121.59(14)
C62 C61 C67 119.65(14)
O62 C62 C63 117.85(14)
O62 C62 C61 122.18(14)
C63 C62 C61 119.97(15)
C64 C63 C62 120.06(15)
C64 C63 H62 120.0
C62 C63 H62 120.0
C63 C64 C65 121.00(15)
C63 C64 H64 119.5
C65 C64 H64 119.5
C66 C65 C64 119.14(15)
C66 C65 H65 120.4
C64 C65 H65 120.4
C65 C66 C61 121.21(15)
C65 C66 H66 119.4
C61 C66 H66 119.4
O67 C67 C61 120.99(14)
O67 C67 C6 118.38(14)
C61 C67 C6 120.53(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.7248(16)
S1 C2 1.7318(17)
O5 C5 1.225(2)
O62 C62 1.3559(19)
O62 H62A 0.8405
O67 C67 1.2413(19)
N4 C9 1.364(2)
N4 C3 1.396(2)
N4 C5 1.4298(19)
N8 C9 1.327(2)
N8 C7 1.3503(19)
C2 C3 1.339(2)
C2 H2 0.9500
C3 H3 0.9500
C5 C6 1.429(2)
C6 C7 1.381(2)
C6 C67 1.489(2)
C7 H7 0.9500
C61 C66 1.404(2)
C61 C62 1.411(2)
C61 C67 1.473(2)
C62 C63 1.397(2)
C63 C64 1.376(2)
C63 H62 0.9500
C64 C65 1.397(2)
C64 H64 0.9500
C65 C66 1.384(2)
C65 H65 0.9500
C66 H66 0.9500
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
O62 H62A O67 . 0.84 1.87 2.5906(16) 144
C2 H2 O5 4_666 0.95 2.29 3.146(2) 150
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
C9 S1 C2 C3 -0.18(13)
S1 C2 C3 N4 0.97(18)
C9 N4 C3 C2 -1.52(19)
C5 N4 C3 C2 -178.23(13)
C9 N4 C5 O5 -171.08(14)
C3 N4 C5 O5 5.4(2)
C9 N4 C5 C6 7.34(19)
C3 N4 C5 C6 -176.23(13)
O5 C5 C6 C7 170.03(16)
N4 C5 C6 C7 -8.2(2)
O5 C5 C6 C67 -6.4(3)
N4 C5 C6 C67 175.39(13)
C9 N8 C7 C6 0.0(2)
C5 C6 C7 N8 5.1(2)
C67 C6 C7 N8 -178.29(14)
C7 N8 C9 N4 -1.1(2)
C7 N8 C9 S1 177.67(11)
C3 N4 C9 N8 -179.75(14)
C5 N4 C9 N8 -3.0(2)
C3 N4 C9 S1 1.35(16)
C5 N4 C9 S1 178.12(10)
C2 S1 C9 N8 -179.59(14)
C2 S1 C9 N4 -0.67(12)
C66 C61 C62 O62 -176.96(15)
C67 C61 C62 O62 -2.4(2)
C66 C61 C62 C63 3.3(2)
C67 C61 C62 C63 177.80(14)
O62 C62 C63 C64 177.45(15)
C61 C62 C63 C64 -2.8(2)
C62 C63 C64 C65 0.1(3)
C63 C64 C65 C66 1.9(2)
C64 C65 C66 C61 -1.4(2)
C62 C61 C66 C65 -1.2(2)
C67 C61 C66 C65 -175.63(14)
C66 C61 C67 O67 161.58(15)
C62 C61 C67 O67 -12.8(2)
C66 C61 C67 C6 -14.7(2)
C62 C61 C67 C6 170.93(14)
C7 C6 C67 O67 -40.9(2)
C5 C6 C67 O67 135.67(15)
C7 C6 C67 C61 135.52(15)
C5 C6 C67 C61 -48.0(2)

_cod_database_fobs_code 2240840
