Observation of the solvent enantio-isotope effect in asymmetric ring-opening of cyclic diaryliodoniums with selenocyanate
Li, Yuanyuan; Tao, Chenyu; Duan, Longhui; Gu, Zhenhua; Chemical Science 16 (2025) 6488–6494; doi:10.1039/D5SC00014A

data_1574135
_publ_section_title
;
 Observation of the solvent enantio-isotope effect in asymmetric
 ring-opening of cyclic diaryliodoniums with selenocyanate
;
_journal_issue                   15
_journal_name_full               'Chemical Science'
_journal_page_first              6488
_journal_page_last               6494
_journal_paper_doi               10.1039/D5SC00014A
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C21 H12 I N Se'
_chemical_formula_sum            'C21 H12 I N Se'
_chemical_formula_weight         484.18
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-03-23
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-07-27 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.94350(10)
_cell_length_b                   10.94350(10)
_cell_length_c                   14.74820(10)
_cell_measurement_reflns_used    12145
_cell_measurement_temperature    292.96(13)
_cell_measurement_theta_max      73.3630
_cell_measurement_theta_min      3.0490
_cell_volume                     1766.25(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.96(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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     31.00  71.00   0.50    0.36    --   99.00 -61.00 120.00   80
  2  \w     46.00  72.00   0.50    0.36    --   99.00 -61.00  90.00   52
  3  \w     26.00  66.00   0.50    0.36    --   99.00 -61.00 -30.00   80
  4  \w     27.00  53.00   0.50    0.36    --   99.00 -45.00-180.00   52
  5  \w     27.00  53.00   0.50    0.36    --   99.00 -45.00-120.00   52
  6  \w     27.00  53.00   0.50    0.36    --   99.00 -45.00 -90.00   52
  7  \w     27.00  52.00   0.50    0.36    --   99.00 -45.00 150.00   50
  8  \w     88.00 114.00   0.50    0.36    --   99.00  30.00  90.00   52
  9  \w    129.00 167.00   0.50    0.36    --   99.00  30.00  90.00   76
 10  \w    135.00 167.00   0.50    0.36    --   99.00  61.00  30.00   64
 11  \w     82.00 132.00   0.50    0.36    --   99.00  61.00  30.00  100
 12  \w     75.00 170.00   0.50    0.36    --   99.00 132.00   4.00  190
 13  \w     85.00 172.00   0.50    0.36    --   99.00  90.00 -62.00  174
 14  \w    -29.00  29.00   0.50    0.10    --   45.87 -19.00 -60.00  116
 15  \w    -35.00  30.00   0.50    0.10    --  -45.87  32.00 141.00  130
 16  \w    -25.00  30.00   0.50    0.10    --  -45.87  19.00  90.00  110
 17  \w    -69.00 -26.00   0.50    0.36    --  -99.00  61.00 120.00   86
 18  \w    -25.00  30.00   0.50    0.10    --  -45.87  19.00 -60.00  110
 19  \w   -121.00 -31.00   0.50    0.10    --  -45.87 -32.00 -17.00  180
 20  \w   -116.00 -28.00   0.50    0.36    --  -99.00 132.00   4.00  176
 21  \w   -116.00 -28.00   0.50    0.36    --  -99.00 132.00   4.00  176
 22  \w   -171.00-103.50   0.50    0.36    --  -99.00 -45.00-180.00  135
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0268666000
_diffrn_orient_matrix_UB_12      0.1223540000
_diffrn_orient_matrix_UB_13      0.0477102000
_diffrn_orient_matrix_UB_21      -0.0509934000
_diffrn_orient_matrix_UB_22      -0.0696238000
_diffrn_orient_matrix_UB_23      0.0825174000
_diffrn_orient_matrix_UB_31      0.1284177000
_diffrn_orient_matrix_UB_32      -0.0020511000
_diffrn_orient_matrix_UB_33      0.0427285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13914
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.399
_diffrn_reflns_theta_min         4.040
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    16.593
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.005(6)
_refine_ls_extinction_coef       0.0023(3)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0762P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                3335
_reflns_number_total             3436
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc00014a2.cif
_cod_data_source_block           6-20-2
_cod_depositor_comments
'Adding full bibliography for 1574135--1574136.cif.'
_cod_database_code               1574135
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N I Se S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              53205
_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 1.603
_oxdiff_exptl_absorpt_empirical_full_min 0.700