Highly enantio-selective synthesis of aza-spirocyclic indanones <i>via</i> rhodium catalysis.
Kou, Cai-Lan; Yang, Long; Sun, Ling-Zhi; Li, Meng; Luo, Xi; Guo, Hong-Bo; Xie, Jian-Bo; Organic & biomolecular chemistry 23 (2025) 3542–3546; doi:10.1039/d5ob00291e

data_7160405
_publ_section_title
;
 Highly enantio-selective synthesis of aza-spirocyclic indanones
 <i>via</i> rhodium catalysis.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3542
_journal_page_last               3546
_journal_paper_doi               10.1039/d5ob00291e
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-20
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2025-01-06 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.368(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3191(6)
_cell_length_b                   11.9918(7)
_cell_length_c                   12.3216(6)
_cell_measurement_reflns_used    8708
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      56.942
_cell_measurement_theta_min      3.120
_cell_volume                     1820.21(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11193
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.953
_diffrn_reflns_theta_min         3.120
_diffrn_source_current           2.86
_diffrn_source_power             0.1997996
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.129
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1448 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.8147.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.096(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5822
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0538P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_full    0.612
_reflns_Friedel_fraction_max     0.568
_reflns_number_gt                5397
_reflns_number_total             5822
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00291e3.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 7160405.cif.'
_cod_database_code               7160405
_shelx_shelxl_version_number     2019/1
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27), C37(H37), C38(H38), C39(H39), C40(H40)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              42213
_olex2_submission_special_instructions 'No special instructions were received'