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_7251774
_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         'C37 H38 I N O4 S2'
_chemical_formula_sum            'C37 H38 I N O4 S2'
_chemical_formula_weight         751.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-19
_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                 98.8730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.56250(10)
_cell_length_b                   20.6098(2)
_cell_length_c                   19.3435(2)
_cell_measurement_reflns_used    33044
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9990
_cell_measurement_theta_min      2.2400
_cell_volume                     3372.72(6)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_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    -17.00 100.00   0.50   25.42    --   10.60  82.00-180.00  234
  2  \w    -79.00  48.00   0.50   25.42    --   10.60 -38.00-150.00  254
  3  \w    -15.00 100.00   0.50   25.42    --   10.60  77.00  30.00  230
  4  \w    -17.00 100.00   0.50   25.42    --   10.60  82.00 120.00  234
  5  \w   -100.00  17.00   0.50   25.42    --  -10.90 -82.00 -90.00  234
  6  \w   -100.00  15.00   0.50   25.42    --  -10.90 -77.00 -30.00  230
  7  \w    -41.00  79.00   0.50   25.42    --  -10.90  57.00 120.00  240
  8  \w    -79.00  38.00   0.50   25.42    --   10.60 -82.00-180.00  234
  9  \w    -79.00  41.00   0.50   25.42    --   10.60 -57.00 -30.00  240
;
_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      0.0247774000
_diffrn_orient_matrix_UB_12      -0.0105606000
_diffrn_orient_matrix_UB_13      -0.0314860000
_diffrn_orient_matrix_UB_21      -0.0119274000
_diffrn_orient_matrix_UB_22      -0.0326941000
_diffrn_orient_matrix_UB_23      0.0093207000
_diffrn_orient_matrix_UB_31      -0.0792962000
_diffrn_orient_matrix_UB_32      0.0016127000
_diffrn_orient_matrix_UB_33      -0.0172429000
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            62070
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.054
_diffrn_reflns_theta_min         1.976
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62505
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.262
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+8.4380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6158
_reflns_number_total             7155
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5gc06338h2.cif
_cod_data_source_block           k11001-jjw-b
_cod_depositor_comments
'Adding full bibliography for 7251770--7251775.cif.'
_cod_database_code               7251774
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.808
_shelx_estimated_absorpt_t_min   0.768
_reflns_odcompleteness_completeness 99.77
_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 Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C16(H16A,H16B), C30(H30A,
 H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19),
 C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32),
  C33(H33), C35(H35), C36(H36)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              11020
_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 1.187
_oxdiff_exptl_absorpt_empirical_full_min 0.692