Diastereoselective construction of complex spiroheterocycles via γ-C(sp3)–H functionalization of 1,1-disubstituted cyclohexanes with diverse bifunctional reagents
Mutra, Mohana Reddy; Chandana, T. L.; Chen, Hsing-Yin; Wang, Yun-Jou; Wang, Jeh-Jeng; Green Chemistry 28 (2026) 5753–5766; doi:10.1039/D5GC06338H

data_7251772
_publ_section_title
;
 Diastereoselective construction of complex spiroheterocycles via
 \g-C(sp3)--H functionalization of 1,1-disubstituted cyclohexanes with
 diverse bifunctional reagents
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              5753
_journal_page_last               5766
_journal_paper_doi               10.1039/D5GC06338H
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C36 H36 Cl N O4 S2 Se'
_chemical_formula_sum            'C36 H36 Cl N O4 S2 Se'
_chemical_formula_weight         725.19
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-01-28
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2026-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.898(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2587(3)
_cell_length_b                   14.3099(3)
_cell_length_c                   22.3142(5)
_cell_measurement_reflns_used    15836
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8910
_cell_measurement_theta_min      2.3290
_cell_volume                     3226.99(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.954
_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    -79.00 100.00   0.50    6.82    --   10.60   0.00 -60.00  358
  2  \w    -20.00 100.00   0.50    6.82    --   10.60  57.00 120.00  240
  3  \w    -79.00  38.00   0.50    6.82    --   10.60 -82.00   0.00  234
  4  \w    -15.00 100.00   0.50    6.82    --   10.60  77.00 120.00  230
  5  \w    -20.00 100.00   0.50    6.82    --   10.60  57.00 -60.00  240
  6  \w      4.00  30.00   0.50    6.82    --   10.60  77.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0106835000
_diffrn_orient_matrix_UB_12      -0.0137351000
_diffrn_orient_matrix_UB_13      -0.0293037000
_diffrn_orient_matrix_UB_21      -0.0321843000
_diffrn_orient_matrix_UB_22      -0.0431254000
_diffrn_orient_matrix_UB_23      0.0032457000
_diffrn_orient_matrix_UB_31      -0.0614831000
_diffrn_orient_matrix_UB_32      0.0201664000
_diffrn_orient_matrix_UB_33      -0.0130981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.021
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0363P)^2^+3.7544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5621
_reflns_number_total             6740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc06338h2.cif
_cod_data_source_block           k11001-jjw-h
_cod_depositor_comments
'Adding full bibliography for 7251770--7251775.cif.'
_cod_database_code               7251772
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.676
_shelx_estimated_absorpt_t_min   0.637
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B), C4(H4A,H4B), C30(H30A,H30B),
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C26(H26), C22(H22), C33(H33), C20(H20), C18(H18), C35(H35),
 C19(H19), C21(H21), C6(H6), C7(H7), C25(H25), C27(H27), C9(H9), C10(H10),
 C32(H32), C36(H36), C28(H28)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              36508
_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 1.389
_oxdiff_exptl_absorpt_empirical_full_min 0.761