Organo-selenium mediated regio- and stereoselective iodoselenylation of alkynes in an aqueous medium: simple access to (E)-β-iodoalkenyl selenides.
Zeng, Xianghua; Chen, Lu; Organic & biomolecular chemistry 17 (2019) 3338–3342; doi:10.1039/c9ob00524b

data_7156727
_publ_section_title
;
 Organo-selenium mediated regio- and stereoselective iodoselenylation of
 alkynes in an aqueous medium: simple access to (E)-\b-iodoalkenyl
 selenides.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3338
_journal_page_last               3342
_journal_paper_doi               10.1039/c9ob00524b
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C21 H18 I N O2 S Se'
_chemical_formula_sum            'C21 H18 I N O2 S Se'
_chemical_formula_weight         554.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-29 deposited with the CCDC.    2019-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                95.706(4)
_cell_angle_beta                 92.226(4)
_cell_angle_gamma                91.500(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8813(4)
_cell_length_b                   9.4987(5)
_cell_length_c                   13.5549(7)
_cell_measurement_reflns_used    3821
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1070
_cell_measurement_theta_min      2.5070
_cell_volume                     1008.50(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -40.00  60.00   1.00    1.00    --  -11.43  77.00   0.00  100
  2  \w     -6.00  88.00   1.00    1.00    --   11.74  77.00 120.00   94
  3  \w    -20.00  88.00   1.00    1.00    --   11.74  77.00 -90.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0716649000
_diffrn_orient_matrix_UB_12      0.0080544000
_diffrn_orient_matrix_UB_13      0.0335985000
_diffrn_orient_matrix_UB_21      0.0532239000
_diffrn_orient_matrix_UB_22      0.0100532000
_diffrn_orient_matrix_UB_23      -0.0398822000
_diffrn_orient_matrix_UB_31      -0.0122750000
_diffrn_orient_matrix_UB_32      0.0739661000
_diffrn_orient_matrix_UB_33      0.0071341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_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            7163
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.156
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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    1.825
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0282P)^2^+0.0628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3120
_reflns_number_total             3563
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00524b2.cif
_cod_data_source_block           jm1121
_cod_depositor_comments          'Adding full bibliography for 7156727.cif.'
_cod_database_code               7156727
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.98
_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:
 C7(H7), C11(H11), C10(H10), C2(H2), C6(H6), C13(H13), C14(H14), C19(H19),
 C20(H20), C16(H16), C3(H3), C5(H5), C17(H17), C4(H4)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.168
_oxdiff_exptl_absorpt_empirical_full_min 0.744