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_7156215
_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         'C25 H18 O4 S'
_chemical_formula_sum            'C25 H18 O4 S'
_chemical_formula_weight         414.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2018-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-16 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.37(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2549(16)
_cell_length_b                   20.063(5)
_cell_length_c                   14.429(4)
_cell_measurement_reflns_used    1187
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8160
_cell_measurement_theta_min      2.4860
_cell_volume                     2059.0(9)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   25.00    --   30.00  54.00 240.00  195
  2  \w    -75.00  30.00   1.00   25.00    --   30.00  54.00   0.00  105
;
_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      0.0151079000
_diffrn_orient_matrix_UB_12      -0.0213060000
_diffrn_orient_matrix_UB_13      0.0399475000
_diffrn_orient_matrix_UB_21      0.0120450000
_diffrn_orient_matrix_UB_22      0.0281939000
_diffrn_orient_matrix_UB_23      0.0303670000
_diffrn_orient_matrix_UB_31      -0.0977884000
_diffrn_orient_matrix_UB_32      0.0001018000
_diffrn_orient_matrix_UB_33      -0.0001412000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.761
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01306
_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    1.337
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0850
_refine_ls_shift/su_max          0.000
_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          0.1909
_refine_ls_wR_factor_ref         0.2527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1843
_reflns_number_total             3640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob00402a2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7156214--7156215.cif.'
_cod_database_code               7156215
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 86.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.90
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00O(H00C,H00D,H00E)
;
_shelx_res_checksum              46229
_shelx_hkl_checksum              90020
_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 37.438
_oxdiff_exptl_absorpt_empirical_full_min 0.489