Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyran naphthoquinones and cytotoxicity against cancer cell lines.
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.; Organic & biomolecular chemistry 9 (2011) 4315–4322; doi:10.1039/c1ob05209h

data_7151922
_publ_section_title
;
 Synthesis of new 9-hydroxy-\a- and 7-hydroxy-\b-pyran naphthoquinones
 and cytotoxicity against cancer cell lines.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; 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       '\w 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/[\s^2^(Fo^2^)+(0.0529P)^2^+0.4095P] where P=(Fo^2^+2Fc^2^)/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