Catalyst-free <i>gem</i>-chlorosulfurization of difluoromethyl-substituted diazo compounds with disulfide and PhICl<sub>2</sub>.
Li, Jiuling; Li, Bin; Chen, Juan; Jia, Xinyu; Wang, Min; Hao, Chengjun; Zheng, Xinhua; Dai, Hongmei; Hu, Wenhao; Organic & biomolecular chemistry 19 (2021) 8030–8034; doi:10.1039/d1ob01422f

data_7158272
_publ_section_title
;
 Catalyst-free <i>gem</i>-chlorosulfurization of
 difluoromethyl-substituted diazo compounds with disulfide and
 PhICl<sub>2</sub>.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8030
_journal_page_last               8034
_journal_paper_doi               10.1039/d1ob01422f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H12 Cl F3 O2 S2'
_chemical_formula_sum            'C15 H12 Cl F3 O2 S2'
_chemical_formula_weight         380.82
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-04-14 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.357(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7553(2)
_cell_length_b                   6.4721(3)
_cell_length_c                   28.2921(10)
_cell_measurement_reflns_used    3020
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4030
_cell_measurement_theta_min      3.1200
_cell_volume                     1589.98(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.942
_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      0.00  57.00   0.50    2.00    --   46.62-106.00 -87.00  114
  2  \w     68.00 107.00   0.50    5.00    --  105.44-106.00 -87.00   78
  3  \w     86.00 112.00   0.50    5.00    --  105.44 -15.00-150.00   52
  4  \w     39.00  65.00   0.50    5.00    --  105.44 -15.00-150.00   52
  5  \w    -15.00  27.00   0.50    2.00    --   46.62 -38.00-180.00   84
  6  \w     85.00 169.00   0.50    5.00    --  105.44 106.00  11.00  168
  7  \w     47.00 112.00   0.50    5.00    --  105.44-125.00 150.00  130
  8  \w    -85.00   1.00   0.50    2.00    --  -46.62 106.00  11.00  172
  9  \w    -84.00 -25.00   0.50    5.00    -- -100.00  30.00  60.00  118
 10  \w   -106.00 -30.00   0.50    5.00    -- -100.00 106.00  11.00  152
 11  \w   -110.00 -28.00   0.50    5.00    -- -100.00 125.00 120.00  164
 12  \w   -169.00 -80.00   0.50    5.00    -- -100.00 -77.00 -60.00  178
 13  \w   -106.00 -71.00   0.50    2.00    --  -46.62-125.00 -30.00   70
 14  \w   -116.00 -72.00   0.50    2.00    --  -46.62-125.00  30.00   88
 15  \w   -111.00 -74.00   0.50    2.00    --  -46.62-125.00  60.00   74
 16  \w   -151.00-126.00   0.50    5.00    -- -100.00-106.00 -87.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0802851000
_diffrn_orient_matrix_UB_12      -0.1808206000
_diffrn_orient_matrix_UB_13      -0.0221921000
_diffrn_orient_matrix_UB_21      0.0368569000
_diffrn_orient_matrix_UB_22      0.1424831000
_diffrn_orient_matrix_UB_23      -0.0407097000
_diffrn_orient_matrix_UB_31      0.1537693000
_diffrn_orient_matrix_UB_32      0.0604133000
_diffrn_orient_matrix_UB_33      0.0294627000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.864
_diffrn_reflns_theta_min         3.150
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0596P)^2^+1.3891P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2406
_reflns_number_total             3122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01422f2.cif
_cod_data_source_block           lijl_200413
_cod_depositor_comments          'Adding full bibliography for 7158272.cif.'
_cod_database_code               7158272
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHSOF
_shelx_estimated_absorpt_t_max   0.790
_shelx_estimated_absorpt_t_min   0.438
_diffrn_oxdiff_digest_frames
;
01c0cb9cc2421239b8b68fb3cbf568736f000288790
;
_diffrn_oxdiff_digest_hkl
;
01277b5a1b491290fb7a133636aa3a11d54468
;
_reflns_odcompleteness_completeness 99.87
_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. Uiso/Uaniso restraints and constraints
Uanis(F16) = Uanis(F16A)
3. Others
 Sof(H6)=Sof(F16A)=1-FVAR(1)
 Sof(F16)=Sof(H2)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C22(H22), C19(H19), C20(H20), C6(H6), C2(H2), C5(H5), C4(H4), C3(H3)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              5287
_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 2.330
_oxdiff_exptl_absorpt_empirical_full_min 0.240