Organocatalytic asymmetric electrophilic tandem selenylation semipinacol rearrangement of 1-(1-arylvinyl)cyclobutanols
Cao, Ren-Fei; Wei, Zheng-Wei; Li, Shu-Kun; Ding, Tong-Mei; Ke, Hua; Chen, Zhi-Min; Chemical Communications 61 (2025) 8532–8535; doi:10.1039/D5CC01919B

data_7134529
_publ_section_title
;
 Organocatalytic asymmetric electrophilic tandem selenylation semipinacol
 rearrangement of 1-(1-arylvinyl)cyclobutanols
;
_journal_issue                   47
_journal_name_full               'Chemical Communications'
_journal_page_first              8532
_journal_page_last               8535
_journal_paper_doi               10.1039/D5CC01919B
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration R
_chemical_formula_moiety         'C19 H19 N O4 Se'
_chemical_formula_sum            'C19 H19 N O4 Se'
_chemical_formula_weight         404.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-20
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-03-12 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.6226(2)
_cell_length_b                   19.4121(2)
_cell_length_c                   7.06020(10)
_cell_measurement_reflns_used    23552
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.4220
_cell_measurement_theta_min      2.8300
_cell_volume                     3511.66(7)
_computing_cell_refinement       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.141a 64-bit (release 04-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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   -112.00 -72.00   0.50    0.05    --  -47.70   0.00   0.00   80
  2  \w    -54.00  21.00   0.50    0.05    --  -47.70  74.00  68.00  150
  3  \w    -13.00  26.00   0.50    0.05    --  -47.70  19.00 120.00   78
  4  \w    -10.00  27.00   0.50    0.05    --  -47.70  19.00  30.00   74
  5  \w   -108.00 -37.00   0.50    0.22    -- -101.00  77.00 -90.00  142
  6  \w   -108.00 -83.00   0.50    0.22    -- -101.00 111.00 -46.13   50
  7  \w    -99.00 -54.00   0.50    0.22    -- -101.00  74.00  68.00   90
  8  \w    -55.00 -30.00   0.50    0.22    -- -101.00 105.00  19.18   50
  9  \w   -107.00 -81.00   0.50    0.22    -- -101.00 105.00  19.18   52
 10  \w    -76.00 -50.00   0.50    0.22    -- -101.00 111.00 -46.13   52
 11  \w    -63.00 -30.00   0.50    0.22    -- -101.00  57.00 -90.00   66
 12  \w   -174.00-130.00   0.50    0.22    -- -101.00 -19.00 -30.00   88
 13  \w   -168.00 -86.00   0.50    0.22    -- -101.00 -57.00  30.00  164
 14  \w   -165.00 -86.00   0.50    0.22    -- -101.00 -57.00   0.00  158
 15  \w    -86.00 -34.00   0.50    0.05    --  -47.70 -74.00 -59.00  104
 16  \w   -171.00 -80.00   0.50    0.22    -- -101.00 -74.00 -59.00  182
 17  \w   -113.00 -88.00   0.50    0.22    -- -101.00 -19.00 -30.00   50
 18  \w   -128.00 -95.00   0.50    0.22    -- -101.00 -37.00  90.00   66
 19  \w   -174.00-138.00   0.50    0.22    -- -101.00 -37.00  90.00   72
 20  \w    -25.00  19.00   0.50    0.05    --   47.70 -19.00 -60.00   88
 21  \w     12.00  61.00   0.50    0.05    --   47.70 -74.00 -59.00   98
 22  \w     71.00  96.00   0.50    0.22    --  107.11 -74.00 -59.00   50
 23  \w     43.00  70.00   0.50    0.22    --  107.11 -57.00-180.00   54
 24  \w     37.00  69.00   0.50    0.22    --  107.11 -57.00  90.00   64
 25  \w     35.00  70.00   0.50    0.22    --  107.11 -57.00 120.00   70
 26  \w     35.00  69.00   0.50    0.22    --  107.11 -57.00 150.00   68
 27  \w    119.00 144.00   0.50    0.22    --  107.11   0.00  30.00   50
 28  \w     87.00 119.00   0.50    0.22    --  107.11  74.00  68.00   64
 29  \w     27.00 118.00   0.50    0.05    --   47.70  74.00  68.00  182
 30  \w    130.00 174.00   0.50    0.22    --  107.11  74.00  68.00   88
 31  \w    112.00 172.00   0.50    0.22    --  107.11   0.00-120.00  120
 32  \w     19.00  93.00   0.50    0.05    --   47.70-125.00 -60.00  148
 33  \w     42.00  68.00   0.50    0.22    --  107.11-125.00   0.00   52
 34  \w     57.00  97.00   0.50    0.22    --  107.11 -99.00 -60.00   80
 35  \w     40.00  73.00   0.50    0.22    --  107.11 -99.00-150.00   66
 36  \w     86.00 111.00   0.50    0.22    --  107.11-125.00   0.00   50
 37  \w     79.00 104.00   0.50    0.22    --  107.11 -99.00   0.00   50
 38  \w     41.00 104.00   0.50    0.22    --  107.11-125.00  90.00  126
 39  \w     81.00 106.00   0.50    0.22    --  107.11 -99.00 120.00   50
 40  \w     61.00  86.00   0.50    0.22    --  107.11 -99.00 150.00   50
 41  \w     39.00  64.00   0.50    0.22    --  107.11-125.00 150.00   50
 42  \w     38.00  66.00   0.50    0.22    --  107.11 -99.00 120.00   56
 43  \w     73.00 106.00   0.50    0.22    --  107.11 -99.00  90.00   66
 44  \w     81.00 106.00   0.50    0.22    --  107.11 -99.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1224773000
_diffrn_orient_matrix_UB_12      0.0492028000
_diffrn_orient_matrix_UB_13      -0.0097216000
_diffrn_orient_matrix_UB_21      0.0323656000
_diffrn_orient_matrix_UB_22      0.0027865000
_diffrn_orient_matrix_UB_23      0.0784032000
_diffrn_orient_matrix_UB_31      0.1776404000
_diffrn_orient_matrix_UB_32      -0.0344503000
_diffrn_orient_matrix_UB_33      -0.0075620000
_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  0.0488
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            45936
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.008
_diffrn_reflns_theta_min         2.856
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 2702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         7259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0685P)^2^+2.9046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1262
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                6699
_reflns_number_total             7259
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01919b2.cif
_cod_data_source_block           crf-10-23a_auto
_cod_depositor_comments
'Adding full bibliography for 7134529--7134530.cif.'
_cod_database_code               7134529
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Se  CHON'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.747
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H6 of C6, H3 of C3, H7 of C7, H36 of C36, H17 of C17,
  H16 of C16, H37 of C37, H38 of C38, H15 of C15, H22 of C22, H35 of C35, H18
  of C18, H25 of C25, H26 of C26, H34 of C34
 At 1.5 times of:
  All C(H,H,H) groups, H19 of C19
2. Uiso/Uaniso restraints and constraints
Uanis(O6) = Uanis(O7)
Uanis(O2) = Uanis(O3)
Uanis(O2) = Uanis(N1)
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C27(H27A,H27B),
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18), C22(H22),
 C25(H25), C26(H26), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              17568
_shelx_hkl_checksum              9842
_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.424