Cobalt-catalyzed conformationally restricted alkylarylation enables divergent access to Csp<sup>3</sup>-rich N-heterocycles.
Chen, Kaixin; Lin, Jie; Jing, Jing; Wang, Junda; Hu, Jiayu; Yi, Hong; Lei, Aiwen; Li, Jie; Chemical science 15 (2024) 16250–16258; doi:10.1039/d4sc04056b

data_1572482
_publ_section_title
;
 Cobalt-catalyzed conformationally restricted alkylarylation enables
 divergent access to Csp<sup>3</sup>-rich N-heterocycles.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              16250
_journal_page_last               16258
_journal_paper_doi               10.1039/d4sc04056b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H22 Cl F3 N2'
_chemical_formula_sum            'C23 H22 Cl F3 N2'
_chemical_formula_weight         418.87
_chemical_name_systematic
1-(4-chlorobenzyl)-3,3-difluoro-3a-(4-fluorobenzyl)octahydro-1H-indole-2-carbonitrile
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-02-02 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.393(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.175(2)
_cell_length_b                   8.8838(10)
_cell_length_c                   16.016(3)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      26.4070
_cell_measurement_theta_min      2.5600
_cell_volume                     2024.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      220(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10642
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0575P)^2^+0.1367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2714
_reflns_number_total             4103
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04056b2.cif
_cod_data_source_block           test1
_cod_depositor_comments
'Adding full bibliography for 1572482--1572485.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572482
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.876
_shelx_estimated_absorpt_t_max   0.935
_shelx_res_checksum              39247
_shelx_hkl_checksum              61284