#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/59/7155911.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_7155911
loop_
_publ_author_name
'Urriolabeitia, Esteban Pablo'
'Ruiz, Sara'
'Carrera, Clara'
'Villuendas, Pedro'
_publ_section_title
;
 Ru-catalysed synthesis of fused heterocycle-pyridinones and -pyrones
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01497J
_journal_year                    2017
_chemical_formula_moiety         'C9 H9 N O S'
_chemical_formula_sum            'C9 H9 N O S'
_chemical_formula_weight         179.23
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_Hall           'I 4bw -2c'
_space_group_name_H-M_alt        'I 41 c d'
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-16 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   14.6413(4)
_cell_length_b                   14.6413(4)
_cell_length_c                   32.7707(19)
_cell_measurement_reflns_used    1791
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.3660
_cell_measurement_theta_min      3.1340
_cell_volume                     7025.0(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            24005
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.982
_diffrn_reflns_theta_max         24.982
_diffrn_reflns_theta_min         3.048
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.316
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             3008
_refine_diff_density_max         1.207
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_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     221
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0767
_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)+(0.1162P)²+0.3651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.2250
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1868
_reflns_number_total             3093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob01497j2.cif
_cod_data_source_block           '__3ab'
_cod_original_cell_volume        7025.0(6)
_cod_database_code               7155911
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.1538(2) 0.8923(2) 0.05259(8) 0.0558(9) Uani 1 1 d . .
C1 C 0.2696(8) 0.8917(8) 0.0487(4) 0.055(3) Uani 1 1 d . .
H1A H 0.3088 0.8957 0.0710 0.066 Uiso 1 1 calc R U
C2 C 0.2982(8) 0.8847(8) 0.0094(4) 0.058(3) Uani 1 1 d . .
H2A H 0.3594 0.8842 0.0018 0.070 Uiso 1 1 calc R U
C3 C 0.2245(7) 0.8783(7) -0.0190(3) 0.042(3) Uani 1 1 d . .
C4 C 0.1434(8) 0.8838(8) 0.0003(3) 0.049(3) Uani 1 1 d . .
C5 C 0.0579(8) 0.8805(8) -0.0201(4) 0.051(3) Uani 1 1 d . .
O1 O -0.0201(6) 0.8813(6) -0.0039(2) 0.066(2) Uani 1 1 d . .
N1 N 0.0673(6) 0.8744(6) -0.0617(3) 0.050(2) Uani 1 1 d . .
H1C H 0.0179 0.8769 -0.0758 0.060 Uiso 1 1 calc R U
C6 C 0.2277(8) 0.8685(8) -0.0628(4) 0.054(3) Uani 1 1 d . .
C7 C 0.1476(8) 0.8648(8) -0.0829(4) 0.050(3) Uani 1 1 d . .
C8 C 0.3191(8) 0.8601(10) -0.0848(4) 0.066(4) Uani 1 1 d . .
H8A H 0.3268 0.9111 -0.1029 0.099 Uiso 1 1 calc R U
H8B H 0.3202 0.8044 -0.1003 0.099 Uiso 1 1 calc R U
H8C H 0.3677 0.8596 -0.0652 0.099 Uiso 1 1 calc R U
C9 C 0.1356(10) 0.8545(10) -0.1283(4) 0.077(4) Uani 1 1 d . .
H9A H 0.1945 0.8500 -0.1411 0.115 Uiso 1 1 calc R U
H9B H 0.1038 0.9067 -0.1389 0.115 Uiso 1 1 calc R U
H9C H 0.1010 0.8003 -0.1339 0.115 Uiso 1 1 calc R U
S11 S -0.0731(2) 0.7720(2) 0.08862(9) 0.0591(9) Uani 1 1 d . .
C11 C -0.0741(8) 0.8893(7) 0.0940(4) 0.056(3) Uani 1 1 d . .
H11A H -0.0633 0.9289 0.0723 0.067 Uiso 1 1 calc R U
C12 C -0.0917(8) 0.9187(8) 0.1321(4) 0.052(3) Uani 1 1 d . .
H12A H -0.0960 0.9799 0.1395 0.062 Uiso 1 1 calc R U
C13 C -0.1031(7) 0.8440(8) 0.1596(3) 0.046(3) Uani 1 1 d . .
C14 C -0.0958(7) 0.7609(8) 0.1394(3) 0.046(3) Uani 1 1 d . .
C15 C -0.1069(8) 0.6738(8) 0.1603(3) 0.051(3) Uani 1 1 d . .
O11 O -0.1040(6) 0.5985(5) 0.1430(3) 0.065(3) Uani 1 1 d . .
N11 N -0.1191(6) 0.6831(7) 0.2010(3) 0.050(2) Uani 1 1 d . .
H11C H -0.1239 0.6335 0.2149 0.060 Uiso 1 1 calc R U
C16 C -0.1187(7) 0.8473(7) 0.2025(3) 0.046(3) Uani 1 1 d . .
C17 C -0.1245(8) 0.7641(8) 0.2224(4) 0.051(3) Uani 1 1 d . .
C18 C -0.1289(9) 0.9374(8) 0.2240(4) 0.070(4) Uani 1 1 d . .
H18A H -0.1145 0.9300 0.2524 0.105 Uiso 1 1 calc R U
H18B H -0.1906 0.9585 0.2213 0.105 Uiso 1 1 calc R U
H18C H -0.0880 0.9811 0.2121 0.105 Uiso 1 1 calc R U
C19 C -0.1378(9) 0.7553(8) 0.2673(3) 0.058(3) Uani 1 1 d . .
H19A H -0.1895 0.7168 0.2726 0.087 Uiso 1 1 calc R U
H19B H -0.1482 0.8146 0.2789 0.087 Uiso 1 1 calc R U
H19C H -0.0841 0.7288 0.2793 0.087 Uiso 1 1 calc R U
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
C1 S1 C4 90.8(6)
C2 C1 S1 112.3(9)
C1 C2 C3 113.0(11)
C4 C3 C2 110.8(10)
C4 C3 C6 120.1(10)
C2 C3 C6 129.1(11)
C3 C4 C5 123.7(11)
C3 C4 S1 113.1(9)
C5 C4 S1 123.2(9)
O1 C5 N1 120.6(11)
O1 C5 C4 127.0(11)
N1 C5 C4 112.4(10)
C5 N1 C7 126.5(10)
C7 C6 C3 117.5(11)
C7 C6 C8 122.0(11)
C3 C6 C8 120.5(11)
C6 C7 N1 119.6(11)
C6 C7 C9 126.1(11)
N1 C7 C9 114.3(11)
C14 S11 C11 89.6(6)
C12 C11 S11 114.5(9)
C11 C12 C13 111.4(11)
C14 C13 C16 120.9(10)
C14 C13 C12 111.0(11)
C16 C13 C12 128.1(11)
C13 C14 C15 122.2(10)
C13 C14 S11 113.5(9)
C15 C14 S11 124.3(9)
O11 C15 N11 123.0(10)
O11 C15 C14 124.0(11)
N11 C15 C14 113.0(11)
C15 N11 C17 126.5(10)
C17 C16 C13 116.3(10)
C17 C16 C18 123.1(10)
C13 C16 C18 120.5(10)
N11 C17 C16 121.0(10)
N11 C17 C19 115.8(10)
C16 C17 C19 123.3(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.699(12)
S1 C4 1.727(11)
C1 C2 1.359(16)
C2 C3 1.430(15)
C3 C4 1.348(14)
C3 C6 1.443(15)
C4 C5 1.418(16)
C5 O1 1.259(13)
C5 N1 1.372(14)
N1 C7 1.374(15)
C6 C7 1.347(16)
C6 C8 1.524(16)
C7 C9 1.505(16)
S11 C14 1.703(11)
S11 C11 1.727(12)
C11 C12 1.345(15)
C12 C13 1.429(15)
C13 C14 1.391(15)
C13 C16 1.425(15)
C14 C15 1.457(16)
C15 O11 1.241(14)
C15 N11 1.353(13)
N11 C17 1.381(15)
C16 C17 1.383(15)
C16 C18 1.502(15)
C17 C19 1.490(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193235
