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_7246055
_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         'C27 H22 Cl N O2 S Se'
_chemical_formula_sum            'C27 H22 Cl N O2 S Se'
_chemical_formula_weight         538.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-18
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-11 deposited with the CCDC.	2022-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.103(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9543(2)
_cell_length_b                   8.33090(10)
_cell_length_c                   24.4205(4)
_cell_measurement_reflns_used    8198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.4200
_cell_measurement_theta_min      5.5940
_cell_volume                     2377.98(7)
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_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    -89.00 -45.00   0.50    1.11    --    0.00 -57.00 120.00   88
  2  \w    -12.00  20.00   0.50    1.11    --    0.00  37.00-150.00   64
  3  \w     -9.00  16.00   0.50    1.11    --    0.00 -37.00   0.00   50
  4  \w    -31.00  23.00   0.50    1.11    --    0.00 -57.00 120.00  108
  5  \w    -21.00  13.00   0.50    1.11    --    0.00 -37.00-150.00   68
  6  \w    -88.00 -52.00   0.50    1.11    --    0.00 -37.00-150.00   72
  7  \w     36.00 134.00   0.50    4.44    --  107.20 -82.00 120.00  196
  8  \w    155.00 195.00   0.50    4.44    --  107.20  30.00 -90.00   80
  9  \w     23.00 120.00   0.50    4.44    --  107.20 -61.00 120.00  194
 10  \w     88.00 128.00   0.50    4.44    --  107.20  30.00 -90.00   80
 11  \w     98.00 127.00   0.50    4.44    --  107.20 -82.00-180.00   58
 12  \w     33.00  88.00   0.50    4.44    --  107.20 -61.00 -30.00  110
 13  \w    104.00 130.00   0.50    4.44    --  107.20 -61.00 -30.00   52
 14  \w     33.00  59.00   0.50    4.44    --  107.20 -82.00-180.00   52
 15  \w     18.00 126.00   0.50    4.44    --  107.20 -30.00 -60.00  216
 16  \w     48.00  73.00   0.50    4.44    --  107.20 -30.00  90.00   50
 17  \w     86.00 131.00   0.50    4.44    --  107.20 -15.00 -30.00   90
 18  \w     30.00  59.00   0.50    4.44    --  107.20 -15.00 -30.00   58
;
_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      -0.1117573000
_diffrn_orient_matrix_UB_12      -0.0306578000
_diffrn_orient_matrix_UB_13      -0.0432238000
_diffrn_orient_matrix_UB_21      -0.0658135000
_diffrn_orient_matrix_UB_22      -0.0115229000
_diffrn_orient_matrix_UB_23      0.0477314000
_diffrn_orient_matrix_UB_31      -0.0230946000
_diffrn_orient_matrix_UB_32      0.1820700000
_diffrn_orient_matrix_UB_33      -0.0042402000
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.843
_diffrn_reflns_theta_min         4.547
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62820
_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            white
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       needle
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0505P)^2^+1.8284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4568
_reflns_number_total             5039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc04101d2.cif
_cod_data_source_block           exp_1077_satya
_cod_depositor_comments
;
Adding full bibliography for 7246055--7246056.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         215.57
_cod_original_formula_moiety         '0.4(C27 H22 Cl N O2 S Se)'
_cod_original_formula_units_Z            10
_cod_original_cell_volume        2377.98(6)
_cod_original_formula_sum        'C10.80 H8.80 Cl0.40 N0.40 O0.80 S0.40 Se0.40'
_cod_database_code               7246055
_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
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X)
;
_shelx_res_checksum              6276
_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 2.414
_oxdiff_exptl_absorpt_empirical_full_min 0.634