Darzens reaction of thioisatins and sulfonium salts: approach to the synthesis of thiochromenone derivatives with anticancer potency.
Shen, Jinhui; Yang, Yang; Hou, Xiaoli; Zeng, Wenlei; Yu, Aimin; Zhao, Xiaowei; Meng, Xiangtai; Organic & biomolecular chemistry 16 (2018) 3487–3494; doi:10.1039/c8ob00402a

data_7156214
_publ_section_title
;
 Darzens reaction of thioisatins and sulfonium salts: approach to the
 synthesis of thiochromenone derivatives with anticancer potency.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3487
_journal_page_last               3494
_journal_paper_doi               10.1039/c8ob00402a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C17 H12 O3 S'
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-12-12 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                87.057(10)
_cell_angle_beta                 70.068(11)
_cell_angle_gamma                71.080(11)
_cell_formula_units_Z            2
_cell_length_a                   8.2863(10)
_cell_length_b                   8.9590(11)
_cell_length_c                   10.6474(12)
_cell_measurement_reflns_used    1218
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2880
_cell_measurement_theta_min      2.7460
_cell_volume                     701.38(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -75.00 120.00   1.00    8.00    --   30.00  54.00 120.00  195
  2  \w    -75.00  26.00   1.00    8.00    --   30.00  54.00 240.00  101
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0189173000
_diffrn_orient_matrix_UB_12      -0.0576452000
_diffrn_orient_matrix_UB_13      0.0458235000
_diffrn_orient_matrix_UB_21      0.0295186000
_diffrn_orient_matrix_UB_22      0.0506177000
_diffrn_orient_matrix_UB_23      0.0295032000
_diffrn_orient_matrix_UB_31      -0.0897348000
_diffrn_orient_matrix_UB_32      0.0339207000
_diffrn_orient_matrix_UB_33      0.0455357000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3371
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.039
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1570
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1871
_reflns_number_total             2472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00402a2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7156214--7156215.cif.'
_cod_database_code               7156214
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 82.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.94
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C2(H2A), C14(H14), C13(H13), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              14900
_shelx_hkl_checksum              27825
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.829