Transition-metal-free sulfonylations of methylthiolated alkynones to synthesize 3-sulfonylated thioflavones
Feng, Zhi-Wen; Li, Jing; Jiang, Yu-Qin; Tian, Yu; Xu, Gui-Qing; Shi, Xin; Ding, Qing-Jie; Li, Wei; Ma, Chun-Hua; Yu, Bing; New Journal of Chemistry 44 (2020) 14786–14790; doi:10.1039/D0NJ03386C

data_7059898
_publ_section_title
;
 Transition-metal-free sulfonylations of methylthiolated alkynones to
 synthesize 3-sulfonylated thioflavones
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14786
_journal_page_last               14790
_journal_paper_doi               10.1039/D0NJ03386C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C22 H16 O3 S2'
_chemical_formula_sum            'C22 H16 O3 S2'
_chemical_formula_weight         392.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5470)
;
_audit_update_record
;
2019-09-14 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                74.461(4)
_cell_angle_beta                 86.616(3)
_cell_angle_gamma                85.790(3)
_cell_formula_units_Z            2
_cell_length_a                   5.3571(2)
_cell_length_b                   12.7753(6)
_cell_length_c                   13.8969(6)
_cell_measurement_reflns_used    4739
_cell_measurement_temperature    295.5(3)
_cell_measurement_theta_max      71.3710
_cell_measurement_theta_min      5.4860
_cell_volume                     913.08(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_environment      air
_diffrn_ambient_temperature      295.5(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.877
_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    -96.00  -9.00   1.00    1.11    --  -35.62 137.00-128.00   87
  2  \w    -94.00  -7.00   1.00    1.11    --  -35.62 133.00  54.00   87
  3  \w     29.00  94.00   1.00    1.11    --   35.62-133.00 -14.00   65
  4  \w     31.00  96.00   1.00    1.11    --   35.62-137.00 168.00   65
  5  \w     39.00 127.00   1.00    4.43    --  107.12-137.00 168.00   88
  6  \w     90.00 176.00   1.00    4.43    --  107.12 133.00  54.00   86
  7  \w     87.00 175.00   1.00    4.43    --  107.12 137.00-128.00   88
  8  \w     39.00 123.00   1.00    4.43    --  107.12-133.00 -14.00   84
  9  \w   -105.00 -17.00   1.00    1.11    --  -35.62 -38.00 -90.00   88
 10  \w   -107.00  -6.00   1.00    1.11    --  -35.62 -19.00 150.00  101
 11  \w   -108.00 -35.00   1.00    1.11    --  -35.62-178.00  30.00   73
 12  \w     19.00 103.00   1.00    1.11    --   35.62  57.00 -90.00   84
 13  \w     57.00 108.00   1.00    1.11    --   35.62 178.00  90.00   51
 14  \w     57.00 108.00   1.00    1.11    --   35.62 178.00 150.00   51
 15  \w     57.00 108.00   1.00    1.11    --   35.62 178.00 -90.00   51
 16  \w    100.00 177.00   1.00    4.43    --  107.12 111.00 150.00   77
 17  \w     36.00 146.00   1.00    4.43    --  107.12 -15.00-180.00  110
 18  \w     80.00 140.00   1.00    4.43    --  107.12  77.00  30.00   60
 19  \w     41.00 134.00   1.00    4.43    --  107.12 -77.00 -60.00   93
 20  \w     49.00 125.00   1.00    4.43    --  107.12 -30.00   0.00   76
 21  \w     41.00 102.00   1.00    4.43    --  107.12 -77.00 120.00   61
 22  \w     75.00 101.00   1.00    4.43    --  107.12 -95.00  60.00   26
 23  \w    106.00 132.00   1.00    4.43    --  107.12 111.00 120.00   26
 24  \w     42.00 118.00   1.00    4.43    --  107.12 -61.00-180.00   76
 25  \w     39.00  65.00   1.00    4.43    --  107.12 -95.00 120.00   26
 26  \w     85.00 110.00   1.00    4.43    --  107.12 -95.00 120.00   25
 27  \w     94.00 132.00   1.00    4.43    --  107.12  61.00 -30.00   38
 28  \w     45.00  71.00   1.00    4.43    --  107.12 -45.00 -60.00   26
 29  \w     39.00 129.00   1.00    4.43    --  107.12 -30.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0115234000
_diffrn_orient_matrix_UB_12      0.0729903000
_diffrn_orient_matrix_UB_13      -0.1079928000
_diffrn_orient_matrix_UB_21      -0.0079795000
_diffrn_orient_matrix_UB_22      -0.1010927000
_diffrn_orient_matrix_UB_23      -0.0399609000
_diffrn_orient_matrix_UB_31      -0.2882523000
_diffrn_orient_matrix_UB_32      0.0132345000
_diffrn_orient_matrix_UB_33      0.0015114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.877
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7397
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.482
_diffrn_reflns_theta_min         3.597
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0374
_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/[\s^2^(Fo^2^)+(0.0579P)^2^+0.2021P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2640
_reflns_number_total             2919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj03386c2.cif
_cod_data_source_block           fzw-20190909
_cod_depositor_comments          'Adding full bibliography for 7059898.cif.'
_cod_database_code               7059898
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 S1'
_shelx_estimated_absorpt_t_max   0.603
_shelx_estimated_absorpt_t_min   0.399
_diffrn_oxdiff_digest_frames
;
016f7b44b857f9037158f882dce09ef3350003348e4
;
_diffrn_oxdiff_digest_hkl
;
010f7daff303c77681589d4aeef2456bdf6421
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C9(H9), C6(H6), C26(H26), C25(H25), C23(H23), C12(H12), C7(H7),
 C14(H14), C8(H8), C16(H16), C15(H15), C13(H13)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              1953
_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 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.509