100% atom-economical and highly regio- and stereoselective iodosulfenylation of alkynes: a reagentless and sustainable approach to access (E)-β-iodoalkenyl sulfides and (Z)-tamoxifen
Satyanarayana, Appanapalli N. V.; Mukherjee, Nilanjana; Chatterjee, Tanmay; Green Chemistry 25 (2023) 779–788; doi:10.1039/D2GC04101D

data_7246056
_publ_section_title
;
 100% atom-economical and highly regio- and stereoselective
 iodosulfenylation of alkynes: a reagentless and sustainable approach to
 access (E)-\b-iodoalkenyl sulfides and (Z)-tamoxifen
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              779
_journal_page_last               788
_journal_paper_doi               10.1039/D2GC04101D
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C21 H14 I N S2'
_chemical_formula_sum            'C21 H14 I N S2'
_chemical_formula_weight         471.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-06
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.03.08 svn.r54f81f84 for OlexSys, GUI svn.r6487)
;
_audit_update_record
;
2022-12-06 deposited with the CCDC.	2022-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.270(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.9022(3)
_cell_length_b                   6.05370(10)
_cell_length_c                   34.1626(6)
_cell_measurement_reflns_used    8441
_cell_measurement_temperature    220
_cell_measurement_theta_max      79.5250
_cell_measurement_theta_min      5.1930
_cell_volume                     3701.45(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      220
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -18.00  48.00   0.50    0.91    --    0.00  37.00-150.00  132
  2  \w    -63.00  14.00   0.50    0.91    --    0.00 -37.00 -30.00  154
  3  \w    -28.00   5.00   0.50    0.91    --    0.00 -37.00 -90.00   66
  4  \w     51.00  85.00   0.50    0.91    --    0.00  37.00-150.00   68
  5  \w     84.00 110.00   0.50    7.24    --  107.20 -82.00 -60.00   52
  6  \w    172.00 197.00   0.50    7.24    --  107.20  61.00 150.00   50
  7  \w     89.00 168.00   0.50    7.24    --  107.20  61.00 150.00  158
  8  \w    102.00 140.00   0.50    7.24    --  107.20 -82.00  30.00   76
  9  \w     80.00 153.00   0.50    7.24    --  107.20  82.00 120.00  146
 10  \w    132.00 188.00   0.50    7.24    --  107.20  45.00-150.00  112
 11  \w     45.00 136.00   0.50    7.24    --  107.20 -82.00   0.00  182
 12  \w     91.00 196.00   0.50    7.24    --  107.20  30.00-120.00  210
 13  \w     18.00 132.00   0.50    7.24    --  107.20 -61.00   0.00  228
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0008365000
_diffrn_orient_matrix_UB_12      0.0837280000
_diffrn_orient_matrix_UB_13      0.0425755000
_diffrn_orient_matrix_UB_21      -0.0148216000
_diffrn_orient_matrix_UB_22      0.2369068000
_diffrn_orient_matrix_UB_23      -0.0147363000
_diffrn_orient_matrix_UB_31      -0.0847795000
_diffrn_orient_matrix_UB_32      -0.0406606000
_diffrn_orient_matrix_UB_33      0.0020188000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9498
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         4.942
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
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    1.692
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.997
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.000036(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3395
_refine_ls_number_restraints     227
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0449
_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^)+58.3810P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3373
_reflns_number_total             3395
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04101d2.cif
_cod_data_source_block           exp_903_anvsn-84
_cod_depositor_comments
'Adding full bibliography for 7246055--7246056.cif.'
_cod_database_code               7246056
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C1, C2
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C00P, C00O
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
 C00L, I001, C00P, C1, C00M, C00O, C00J, C2, C00D, S003, C00B, C00N, C00A,
 H00D, C00F, H00L, C007, C00H, C00E, C008, H00A, H00F, S002, N004, C00K, H008,
 C005, C006, C009, C00C, C00I, H009, H00C, C00G, H00G
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Others
 Fixed Sof: C00O(0.55) C00P(0.55) C1(0.45) C2(0.45)
4.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L),
 C00N(H00N)
;
_shelx_res_checksum              85425
_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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.693