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_7131597
_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         'C28 H24 I N O4 S2'
_chemical_formula_sum            'C28 H24 I N O4 S2'
_chemical_formula_weight         629.50
_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_block_doi                 10.5517/ccdc.csd.cc27z1q0
_audit_creation_date             2020-10-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-05-18 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                89.135(2)
_cell_angle_beta                 88.150(2)
_cell_angle_gamma                74.562(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2544(2)
_cell_length_b                   9.7531(2)
_cell_length_c                   30.4790(9)
_cell_measurement_reflns_used    32302
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9960
_cell_measurement_theta_min      2.1670
_cell_volume                     2650.31(11)
_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 (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_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -79.00  41.00   0.50   13.07    --   10.60 -57.00  90.00  240
  2  \w    -79.00  41.00   0.50   13.07    --   10.60 -57.00  60.00  240
  3  \w    -79.00  36.00   0.50   13.07    --   10.60 -77.00   0.00  230
  4  \w    -79.00  41.00   0.50   13.07    --   10.60 -57.00 -30.00  240
  5  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00 150.00  234
  6  \w    -79.00  38.00   0.50   13.07    --   10.60 -82.00  48.35  234
  7  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00-120.00  234
  8  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00 -30.00  234
  9  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00 120.00  234
 10  \w    -20.00 100.00   0.50   13.07    --   10.60  57.00 -90.00  240
 11  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00   0.00  234
 12  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00-180.00  234
 13  \w    -17.00 100.00   0.50   13.07    --   10.60  82.00 -90.00  234
 14  \w   -100.00  17.00   0.50   13.07    --  -10.90 -82.00 -60.00  234
 15  \w   -100.00  17.00   0.50   13.07    --  -10.90 -82.00  90.00  234
 16  \w    -41.00  26.00   0.50   13.07    --  -10.90  57.00-120.00  134
;
_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      0.0536033000
_diffrn_orient_matrix_UB_12      -0.0393088000
_diffrn_orient_matrix_UB_13      -0.0154206000
_diffrn_orient_matrix_UB_21      -0.0425780000
_diffrn_orient_matrix_UB_22      0.0376846000
_diffrn_orient_matrix_UB_23      -0.0174303000
_diffrn_orient_matrix_UB_31      0.0405163000
_diffrn_orient_matrix_UB_32      0.0522235000
_diffrn_orient_matrix_UB_33      0.0007436000
_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  0.0632
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            76298
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.006
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30705
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.872
_refine_diff_density_min         -1.256
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         9290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.274
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+15.0998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8370
_reflns_number_total             9290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00842h2.cif
_cod_data_source_block           k10910-jjw-b(mr-11-c-1)
_cod_depositor_comments
;
Adding full bibliography for 7131597--7131600.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H48 I2 N2 O8 S4'
_cod_original_formula_weight         1259.00
_cod_original_formula_moiety         '2(C28 H24 I N O4 S2)'
_cod_original_formula_units_Z            2
_cod_database_code               7131597
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H24 I N O4 S2'
_diffrn_oxdiff_digest_frames
;
016a88bf19931d206da33dec1c39b0a6d7000256897
;
_diffrn_oxdiff_digest_hkl
;
01a8eccf89a1d952235853c99d96b1e1e77c4a
;
_reflns_odcompleteness_completeness 99.63
_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.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
  C26(H26), C27(H27), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36),
 C38(H38), C39(H39), C41(H41), C42(H42), C45(H45), C46(H46), C47(H47), C48(H48),
  C49(H49), C51(H51), C52(H52), C54(H54), C55(H55)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C), C43(H43A,H43B,H43C), C56(H56A,H56B,
 H56C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              5422
_shelx_hkl_checksum              16075
_shelx_fab_checksum              31300
_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 1.778
_oxdiff_exptl_absorpt_empirical_full_min 0.405