#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151922.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_7151922
loop_
_publ_author_name
'da Rocha, David R.'
'de Souza, Ana C. G.'
'Resende, Jackson A. L. C.'
'Santos, Wilson C.'
'dos Santos, Evelyne A.'
'Pessoa, Cláudia'
'de Moraes, Manoel O.'
'Costa-Lotufo, Letícia V'
'Montenegro, Raquel C.'
'Ferreira, Vitor F.'
_publ_section_title
;
 Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones
 and cytotoxicity against cancer cell lines.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4315
_journal_page_last               4322
_journal_paper_doi               10.1039/c1ob05209h
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H12 O3 S1'
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33
_chemical_name_systematic
;
8-hydroxy-2-(p-tolylthio)naphthalene-1,4-dione
;
_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_date             2010-12-14T15:55:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.821(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9234(7)
_cell_length_b                   8.6499(7)
_cell_length_c                   17.8425(8)
_cell_measurement_reflns_used    1797
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      62.2802
_cell_measurement_theta_min      2.5469
_cell_volume                     1337.33(17)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.94
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0836618
_diffrn_orient_matrix_UB_12      0.1023278
_diffrn_orient_matrix_UB_13      0.047513
_diffrn_orient_matrix_UB_21      -0.1567217
_diffrn_orient_matrix_UB_22      -0.0499378
_diffrn_orient_matrix_UB_23      -0.0515398
_diffrn_orient_matrix_UB_31      -0.0055426
_diffrn_orient_matrix_UB_32      -0.1361195
_diffrn_orient_matrix_UB_33      0.0545862
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3625
_diffrn_reflns_theta_full        60.26
_diffrn_reflns_theta_max         60.26
_diffrn_reflns_theta_min         5.11
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.90767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0529P)²+0.4095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1518
_reflns_number_total             1872
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05209h.txt
_cod_data_source_block           compound8
_cod_original_cell_volume        1337.33(16)
_cod_original_formula_sum        'C17 H12 O3 S1'
_cod_database_code               7151922
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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51154(6) 0.85539(7) 0.23171(3) 0.0277(2) Uani 1 1 d . . .
C11 C 0.3354(3) 0.8812(2) 0.25993(12) 0.0230(5) Uani 1 1 d . . .
O1 O 0.75213(17) 0.89691(17) 0.16032(9) 0.0301(4) Uani 1 1 d . . .
O4 O 0.28125(18) 1.26513(19) 0.02934(9) 0.0357(4) Uani 1 1 d . . .
C14 C 0.0753(3) 0.8973(3) 0.32087(13) 0.0259(5) Uani 1 1 d . . .
C4 C 0.3924(3) 1.1862(2) 0.06091(13) 0.0251(5) Uani 1 1 d . . .
C8A C 0.6651(2) 1.0991(2) 0.07187(12) 0.0223(5) Uani 1 1 d . . .
O8 O 0.92842(17) 1.02219(19) 0.08022(9) 0.0335(4) Uani 1 1 d . . .
H8 H 0.9057 0.9611 0.1124 0.050 Uiso 1 1 calc R . .
C4A C 0.5422(3) 1.1977(2) 0.03801(12) 0.0230(5) Uani 1 1 d . . .
C1 C 0.6486(2) 0.9888(2) 0.13046(12) 0.0234(5) Uani 1 1 d . . .
C7 C 0.8209(3) 1.2203(3) -0.00579(13) 0.0299(6) Uani 1 1 d . . .
H7 H 0.9150 1.2280 -0.0216 0.036 Uiso 1 1 calc R . .
C8 C 0.8054(3) 1.1111(3) 0.04924(13) 0.0257(5) Uani 1 1 d . . .
C5 C 0.5595(3) 1.3055(2) -0.01582(12) 0.0265(5) Uani 1 1 d . . .
H5 H 0.4763 1.3720 -0.0385 0.032 Uiso 1 1 calc R . .
C12 C 0.3262(3) 0.9920(3) 0.31484(13) 0.0269(5) Uani 1 1 d . . .
H12 H 0.4086 1.0630 0.3319 0.032 Uiso 1 1 calc R . .
C2 C 0.5011(2) 0.9877(2) 0.15627(12) 0.0225(5) Uani 1 1 d . . .
C6 C 0.7004(3) 1.3167(3) -0.03707(13) 0.0291(6) Uani 1 1 d . . .
H6 H 0.7125 1.3924 -0.0738 0.035 Uiso 1 1 calc R . .
C16 C 0.2136(3) 0.7802(3) 0.23511(13) 0.0286(5) Uani 1 1 d . . .
H16 H 0.2187 0.7047 0.1971 0.034 Uiso 1 1 calc R . .
C13 C 0.1969(3) 0.9992(3) 0.34472(13) 0.0270(5) Uani 1 1 d . . .
H13 H 0.1915 1.0754 0.3823 0.032 Uiso 1 1 calc R . .
C3 C 0.3821(3) 1.0782(2) 0.12286(12) 0.0235(5) Uani 1 1 d . . .
H3 H 0.2890 1.0723 0.1397 0.028 Uiso 1 1 calc R . .
C15 C 0.0854(3) 0.7880(3) 0.26479(13) 0.0286(6) Uani 1 1 d . . .
H15 H 0.0025 0.7180 0.2469 0.034 Uiso 1 1 calc R . .
C17 C -0.0633(3) 0.9022(3) 0.35463(15) 0.0352(6) Uani 1 1 d . . .
H17A H -0.1552 0.9271 0.3140 0.053 Uiso 1 1 calc R . .
H17C H -0.0482 0.9815 0.3950 0.053 Uiso 1 1 calc R . .
H17B H -0.0770 0.8013 0.3770 0.053 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C11 104.33(10) . . ?
C16 C11 C12 119.2(2) . . ?
C16 C11 S1 120.77(17) . . ?
C12 C11 S1 119.55(17) . . ?
C13 C14 C15 118.1(2) . . ?
C13 C14 C17 121.3(2) . . ?
C15 C14 C17 120.5(2) . . ?
O4 C4 C3 120.8(2) . . ?
O4 C4 C4A 121.1(2) . . ?
C3 C4 C4A 118.05(19) . . ?
C4A C8A C8 119.2(2) . . ?
C4A C8A C1 120.4(2) . . ?
C8 C8A C1 120.4(2) . . ?
C8 O8 H8 109.5 . . ?
C5 C4A C8A 120.4(2) . . ?
C5 C4A C4 119.6(2) . . ?
C8A C4A C4 119.98(19) . . ?
O1 C1 C8A 122.6(2) . . ?
O1 C1 C2 119.00(19) . . ?
C8A C1 C2 118.37(19) . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
O8 C8 C7 117.9(2) . . ?
O8 C8 C8A 122.3(2) . . ?
C7 C8 C8A 119.8(2) . . ?
C4A C5 C6 119.6(2) . . ?
C4A C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C3 C2 C1 121.47(19) . . ?
C3 C2 S1 127.96(17) . . ?
C1 C2 S1 110.57(15) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C2 C3 C4 121.5(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.752(2) . ?
S1 C11 1.775(2) . ?
C11 C16 1.382(3) . ?
C11 C12 1.388(3) . ?
O1 C1 1.238(2) . ?
O4 C4 1.225(3) . ?
C14 C13 1.384(3) . ?
C14 C15 1.395(3) . ?
C14 C17 1.500(3) . ?
C4 C3 1.466(3) . ?
C4 C4A 1.492(3) . ?
C8A C4A 1.407(3) . ?
C8A C8 1.408(3) . ?
C8A C1 1.449(3) . ?
O8 C8 1.346(3) . ?
O8 H8 0.8400 . ?
C4A C5 1.373(3) . ?
C1 C2 1.495(3) . ?
C7 C6 1.370(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C5 C6 1.401(3) . ?
C5 H5 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C2 C3 1.339(3) . ?
C6 H6 0.9500 . ?
C16 C15 1.372(3) . ?
C16 H16 0.9500 . ?
C13 H13 0.9500 . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17B 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 O1 0.84 1.86 2.601(2) 145.6 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S1 C11 C16 100.13(19) . . . . ?
C2 S1 C11 C12 -87.80(18) . . . . ?
C8 C8A C4A C5 -0.7(3) . . . . ?
C1 C8A C4A C5 178.02(19) . . . . ?
C8 C8A C4A C4 179.66(18) . . . . ?
C1 C8A C4A C4 -1.6(3) . . . . ?
O4 C4 C4A C5 4.2(3) . . . . ?
C3 C4 C4A C5 -175.32(19) . . . . ?
O4 C4 C4A C8A -176.1(2) . . . . ?
C3 C4 C4A C8A 4.3(3) . . . . ?
C4A C8A C1 O1 178.00(19) . . . . ?
C8 C8A C1 O1 -3.3(3) . . . . ?
C4A C8A C1 C2 -2.7(3) . . . . ?
C8 C8A C1 C2 175.98(19) . . . . ?
C6 C7 C8 O8 -177.91(19) . . . . ?
C6 C7 C8 C8A 0.7(3) . . . . ?
C4A C8A C8 O8 178.85(18) . . . . ?
C1 C8A C8 O8 0.1(3) . . . . ?
C4A C8A C8 C7 0.3(3) . . . . ?
C1 C8A C8 C7 -178.41(19) . . . . ?
C8A C4A C5 C6 0.1(3) . . . . ?
C4 C4A C5 C6 179.73(19) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
S1 C11 C12 C13 -171.38(16) . . . . ?
O1 C1 C2 C3 -176.1(2) . . . . ?
C8A C1 C2 C3 4.6(3) . . . . ?
O1 C1 C2 S1 3.4(2) . . . . ?
C8A C1 C2 S1 -175.87(15) . . . . ?
C11 S1 C2 C3 -5.2(2) . . . . ?
C11 S1 C2 C1 175.31(14) . . . . ?
C8 C7 C6 C5 -1.3(3) . . . . ?
C4A C5 C6 C7 0.9(3) . . . . ?
C12 C11 C16 C15 -0.7(3) . . . . ?
S1 C11 C16 C15 171.45(17) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
C17 C14 C13 C12 178.4(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
S1 C2 C3 C4 178.68(16) . . . . ?
O4 C4 C3 C2 177.9(2) . . . . ?
C4A C4 C3 C2 -2.5(3) . . . . ?
C11 C16 C15 C14 -0.3(3) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C17 C14 C15 C16 -178.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4981842
2 PubChem 6481302
