Regioselective β-organoseleno/α-,N2-tetrazole addition to alkenes
Zhu, Li-Li; Tian, Lifang; Zhang, Zijian; Li, Qinying; Tian, Yingying; Han, Xiaofeng; Li, Jiawei; Liu, Guang-Lu; Zhang, Hui; Wang, Yahui; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01622C

data_7160911
_publ_section_title
;
 Regioselective \b-organoseleno/\a-,N2-tetrazole addition to alkenes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01622C
_journal_year                    2025
_chemical_formula_moiety         'C25 H26 N4 Se'
_chemical_formula_sum            'C25 H26 N4 Se'
_chemical_formula_weight         461.46
_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             2024-11-17
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-06-29 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.8490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.80560(10)
_cell_length_b                   9.21470(10)
_cell_length_c                   23.0221(3)
_cell_measurement_reflns_used    13821
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5190
_cell_measurement_theta_min      4.1350
_cell_volume                     2234.92(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.923
_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    -27.00  -1.00   0.50    0.05    --   46.52 -21.00-143.00   52
  2  \w     33.00 114.00   0.50    0.05    --   46.52  57.00 -90.00  162
  3  \w     92.00 142.00   0.50    0.05    --  104.59  21.00  22.00  100
  4  \w     88.00 173.00   0.50    0.05    --  104.59  15.00 -60.00  170
  5  \w     59.00 122.00   0.50    0.05    --   46.52  21.00  22.00  126
  6  \w     59.00 111.00   0.50    0.05    --  104.59-125.00 120.00  104
  7  \w    -26.00  36.00   0.50    0.05    --   46.52 -38.00  90.00  124
  8  \w    -30.00   0.00   0.50    0.05    --  -46.52  21.00  22.00   60
  9  \w    -77.00 -51.00   0.50    0.05    --  -97.00  77.00 -90.00   52
 10  \w   -108.00 -38.00   0.50    0.05    --  -97.00  77.00 -60.00  140
 11  \w   -105.00 -79.00   0.50    0.05    --  -97.00  77.00 -90.00   52
 12  \w   -108.00 -79.00   0.50    0.05    --  -97.00  77.00-150.00   58
 13  \w    -74.00 -34.00   0.50    0.05    --  -97.00  77.00-150.00   80
 14  \w    -54.00 -28.00   0.50    0.05    --  -97.00  45.00-180.00   52
 15  \w    -74.00 -34.00   0.50    0.05    --  -97.00  61.00-150.00   80
 16  \w    -51.00 -25.00   0.50    0.05    --  -97.00  45.00   0.00   52
 17  \w    -53.00 -26.00   0.50    0.05    --  -97.00  45.00  30.00   54
 18  \w    -53.00 -26.00   0.50    0.05    --  -97.00  45.00  90.00   54
 19  \w    -73.00 -24.00   0.50    0.05    --  -97.00  61.00 150.00   98
 20  \w    -54.00 -25.00   0.50    0.05    --  -97.00  45.00 150.00   58
 21  \w   -167.00-119.00   0.50    0.05    --  -97.00 -95.00   0.00   96
 22  \w   -107.00 -81.00   0.50    0.05    --  -46.52 -21.00-143.00   52
 23  \w    -69.00 -37.00   0.50    0.05    --  -46.52 -21.00-143.00   64
 24  \w   -161.00 -82.00   0.50    0.05    --  -97.00 -21.00-143.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1317669000
_diffrn_orient_matrix_UB_12      -0.0231957000
_diffrn_orient_matrix_UB_13      0.0137424000
_diffrn_orient_matrix_UB_21      0.0543700000
_diffrn_orient_matrix_UB_22      0.0400080000
_diffrn_orient_matrix_UB_23      0.0656665000
_diffrn_orient_matrix_UB_31      -0.0326775000
_diffrn_orient_matrix_UB_32      0.1606920000
_diffrn_orient_matrix_UB_33      -0.0144006000
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14772
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.462
_diffrn_reflns_theta_min         5.019
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
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    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0452P)^2^+1.9492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4236
_reflns_number_total             4278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01622c2.cif
_cod_data_source_block           99a_auto
_cod_database_code               7160911
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.745
_shelx_estimated_absorpt_t_min   0.714
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00B(H00D), C00D(H00F), C00F(H00G), C00G(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00Q(H00Q), C00S(H00T)
2.d Idealised Me refined as rotating group:
 C00R(H00P,H00R,H00S), C00T(H00U,H00V,H00W), C00U(H00X,H00Y,H)
;
_shelx_res_checksum              30943
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.555