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_7131598
_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         'C22 H17 I O4 S'
_chemical_formula_sum            'C22 H17 I O4 S'
_chemical_formula_weight         504.31
_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     dual
_audit_creation_date             2022-04-06
_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                82.8810(10)
_cell_angle_beta                 74.5730(10)
_cell_angle_gamma                74.1450(10)
_cell_formula_units_Z            2
_cell_length_a                   7.98190(10)
_cell_length_b                   9.84350(10)
_cell_length_c                   13.6204(2)
_cell_measurement_reflns_used    22061
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.0170
_cell_measurement_theta_min      2.1490
_cell_volume                     990.83(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    'ShelXT (Sheldrick, 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    -16.00  99.00   0.50    2.20    --    9.30  75.00-114.00  230
  2  \w    -34.00  79.00   0.50    2.20    --   -9.50  75.00-114.00  226
  3  \w    -98.00  15.00   0.50    2.20    --   -9.50 -75.00 117.00  226
  4  \w    -80.00  35.00   0.50    2.20    --    9.30 -77.00 150.00  230
  5  \w    -16.00  99.00   0.50    2.20    --    9.30  77.00   0.00  230
  6  \w    -80.00  35.00   0.50    2.20    --    9.30 -75.00 117.00  230
  7  \w    -16.00  99.00   0.50    2.20    --    9.30  77.00  60.00  230
  8  \w    -98.00  17.00   0.50    2.20    --   -9.50 -82.00-180.00  230
  9  \w    -98.00  17.00   0.50    2.20    --   -9.50 -82.00-150.00  230
 10  \w    -34.00  79.00   0.50    2.20    --   -9.50  77.00 -60.00  226
 11  \w    -98.00  19.00   0.50    2.20    --   -9.50 -57.00  30.00  234
 12  \w    -98.00  17.00   0.50    2.20    --   -9.50 -82.00  30.00  230
 13  \w    -98.00  17.00   0.50    2.20    --   -9.50 -82.00  60.00  230
 14  \w    -98.00  17.00   0.50    2.20    --   -9.50 -82.00  90.00  230
 15  \w    -34.00  18.00   0.50    2.20    --   -9.50  77.00  30.00  104
;
_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      -0.0522195000
_diffrn_orient_matrix_UB_12      -0.0277814000
_diffrn_orient_matrix_UB_13      0.0445347000
_diffrn_orient_matrix_UB_21      0.0729539000
_diffrn_orient_matrix_UB_22      -0.0600048000
_diffrn_orient_matrix_UB_23      0.0012522000
_diffrn_orient_matrix_UB_31      0.0319542000
_diffrn_orient_matrix_UB_32      0.0354388000
_diffrn_orient_matrix_UB_33      0.0307003000
_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  0.0439
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28905
_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         2.154
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46761
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3490
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0196
_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^)+(0.0182P)^2^+0.6503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3334
_reflns_number_total             3490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00842h2.cif
_cod_data_source_block           k11104-jjw-a(lj3-7)
_cod_depositor_comments
'Adding full bibliography for 7131597--7131600.cif.'
_cod_database_code               7131598
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H30 I2 O8 S2 '
_diffrn_oxdiff_digest_frames
;
0124df88a6e630b57285b40acd32ae252900025b374
;
_diffrn_oxdiff_digest_hkl
;
019c40eea29767eb9ab03a146e1c34c67d52eb
;
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
O1 \\sim O2 \\sim O3 \\sim O4 \\sim S1 \\sim I1: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 3.8A
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 2.563
_oxdiff_exptl_absorpt_empirical_full_min 0.667