Light-mediated sulfonyl-iodination of ynamides and internal alkynes.
Mutra, Mohana Reddy; Li, Jing; Wang, Jeh-Jeng; Chemical communications (Cambridge, England) 59 (2023) 6584–6587; doi:10.1039/d3cc00842h

data_7131600
_publ_section_title
;
 Light-mediated sulfonyl-iodination of ynamides and internal alkynes.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6584
_journal_page_last               6587
_journal_paper_doi               10.1039/d3cc00842h
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         '2(C25 H26 I N O4 S2)'
_chemical_formula_sum            'C50 H52 I2 N2 O8 S4'
_chemical_formula_weight         1190.97
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-01-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-30 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                93.058(4)
_cell_angle_beta                 96.826(4)
_cell_angle_gamma                104.064(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5557(4)
_cell_length_b                   10.3154(5)
_cell_length_c                   29.9202(16)
_cell_measurement_reflns_used    4938
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      16.3850
_cell_measurement_theta_min      2.0350
_cell_volume                     2534.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_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    -17.00 100.00   0.50    0.50    --   10.60  82.00 150.00  234
  2  \w    -17.00 100.00   0.50    0.50    --   10.60  82.00-120.00  234
  3  \w    -17.00 100.00   0.50    0.50    --   10.60  82.00   0.00  234
  4  \w    -17.00 100.00   0.50    0.50    --   10.60  82.00  90.00  234
  5  \w    -79.00  38.00   0.50    0.50    --   10.60 -82.00-180.00  234
  6  \w    -79.00  36.00   0.50    0.50    --   10.60 -77.00  60.00  230
  7  \w    -20.00 100.00   0.50    0.50    --   10.60  57.00   0.00  240
  8  \w    -79.00 100.00   0.50    0.50    --   10.60  19.00-180.00  358
  9  \w    -17.00 100.00   0.50    0.50    --   10.60  82.00-150.00  234
 10  \w    -17.00 100.00   0.50    0.50    --   10.60  82.00 -60.00  234
 11  \w   -100.00 -22.00   0.50    0.50    --  -10.90 -82.00 -60.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0529030000
_diffrn_orient_matrix_UB_12      0.0421861000
_diffrn_orient_matrix_UB_13      0.0179090000
_diffrn_orient_matrix_UB_21      0.0306252000
_diffrn_orient_matrix_UB_22      0.0458367000
_diffrn_orient_matrix_UB_23      -0.0156199000
_diffrn_orient_matrix_UB_31      -0.0608739000
_diffrn_orient_matrix_UB_32      0.0343660000
_diffrn_orient_matrix_UB_33      0.0030846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1503
_diffrn_reflns_av_unetI/netI     0.1325
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            53142
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.043
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.610
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         8908
_refine_ls_number_restraints     1998
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1546
_refine_ls_R_factor_gt           0.0909
_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^)+(0.1083P)^2^+4.3531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5053
_reflns_number_total             8908
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00842h2.cif
_cod_data_source_block           k11101-jjw-c
_cod_depositor_comments
'Adding full bibliography for 7131597--7131600.cif.'
_cod_database_code               7131600
_shelx_shelxl_version_number     2018/3
_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. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41
\\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48 \\sim C49
\\sim C50 \\sim N1 \\sim N2 \\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim
O6 \\sim O7 \\sim O8 \\sim S1 \\sim S2 \\sim S3 \\sim S4 \\sim I1 \\sim I2
\\sim I3: within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 3.8A
3. Others
 Sof(I3)=1-FVAR(1)
 Sof(I2)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C27(H27A,H27B), C28(H28A,H28B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C30(H30), C31(H31), C33(H33),
  C34(H34), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C45(H45),
 C46(H46), C48(H48), C49(H49)
4.c Idealised Me refined as rotating group:
 C3(H3B,H3A,H3C), C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C35(H35A,H35B,H35C), C50(H50A,H50B,H50C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              66629
_shelx_hkl_checksum              21376
_shelx_fab_checksum              18441
_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 2.450
_oxdiff_exptl_absorpt_empirical_full_min 0.627