Iodine-catalysed regioselective thiolation of flavonoids using sulfonyl hydrazides as sulfenylation reagents.
Zhao, Xia; Deng, Zhijie; Wei, Aoqi; Li, Boyang; Lu, Kui; Organic & biomolecular chemistry 14 (2016) 7304–7312; doi:10.1039/c6ob01006g

data_7155205
_publ_section_title
;
 Iodine-catalysed regioselective thiolation of flavonoids using sulfonyl
 hydrazides as sulfenylation reagents.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7304
_journal_page_last               7312
_journal_paper_doi               10.1039/c6ob01006g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C32 H26 O12 S'
_chemical_formula_sum            'C32 H26 O12 S'
_chemical_formula_weight         634.59
_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     direct
_audit_creation_date             2015-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-05-09 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                64.089(3)
_cell_angle_beta                 82.180(2)
_cell_angle_gamma                86.755(2)
_cell_formula_units_Z            2
_cell_length_a                   11.7409(3)
_cell_length_b                   11.8595(3)
_cell_length_c                   11.9319(3)
_cell_measurement_reflns_used    9848
_cell_measurement_temperature    173.00(10)
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_cell_measurement_theta_min      4.1340
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
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_diffrn_measurement_details
;
  1 omega  -50.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4852   38.0000    0.0000 82

  3 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4852   38.0000 -180.0000 83

  4 omega  -44.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4852   38.0000   90.0000 77

  5 omega    6.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852   87.0000  163.9878 28

  6 omega   10.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852   77.0000  -90.0000 84

  7 omega   13.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852   57.0000   30.0000 76

  8 omega    9.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852   77.0000    0.0000 41

  9 omega   46.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852 -125.0000 -180.0000 38

 10 omega   14.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852   57.0000 -150.0000 80

 11 omega   49.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852 -125.0000    0.0000 38

 12 omega    9.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4852   77.0000   90.0000 104

 13 omega   75.00  175.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   77.0000   60.0000 100

 14 omega   80.00  174.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000  150.0000 94

 15 omega  114.00  177.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   77.0000 -180.0000 63

 16 omega   79.00  108.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000   60.0000 29

 17 omega   80.00  106.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000  -30.0000 26

 18 omega   79.00  178.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000 -120.0000 99

 19 omega   55.00  139.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012  -77.0000    0.0000 84

 20 omega  110.00  172.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012  125.0000  -30.0000 62

 21 omega  143.00  173.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   77.0000  -90.0000 30

 22 omega   36.00  103.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012  -94.0000  -90.0000 67

 23 omega   75.00  101.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   77.0000  -90.0000 26

 24 omega   80.00  141.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000    0.0000 61

 25 omega   26.00  106.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012  -94.0000    0.0000 80

 26 omega   76.00  101.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   77.0000 -180.0000 25

 27 omega   79.00  177.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000   30.0000 98

 28 omega   35.00  116.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012 -125.0000 -150.0000 81

 29 omega   80.00  126.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   61.0000 -180.0000 46

 30 omega  118.00  143.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      107.7012   77.0000   90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0191677000
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_diffrn_orient_matrix_UB_21      0.0185411000
_diffrn_orient_matrix_UB_22      0.0354927000
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_diffrn_orient_matrix_UB_33      -0.0061165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15842
_diffrn_reflns_point_group_measured_fraction_full 0.996
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_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.800
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       block
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         5262
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0460
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_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^)+(0.0543P)^2^+0.7508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4707
_reflns_number_total             5262
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01006g2.cif
_cod_data_source_block           a150512c
_cod_depositor_comments          'Adding full bibliography for 7155205.cif.'
_cod_database_code               7155205
_chemical_oxdiff_formula         'C H O N S Zn'
_reflns_odcompleteness_completeness 99.60
_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. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C4(H4), C24(H24), C25(H25), C28(H28), C6(H6), C3(H3), C7(H7)
3.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C22(H22A,H22B,
 H22C), C20(H20A,H20B,H20C), C32(H32A,H32B,H32C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-12
_olex2_submission_special_instructions 'No special instructions were received'