Atroposelective synthesis of isoquinolinone bearing two distinct C−N axes via cobalt-catalyzed enantioselective C−H activation/annulation
Li, Wenkai; Fu, Liling; Xu, Yongqiang; Zhou, Yuhan; Qu, Jingping; Wang, Baomin; Chemical Communications  (2025) –; doi:10.1039/D5CC05883J

data_7135227
_publ_section_title
;
 Atroposelective synthesis of isoquinolinone bearing two distinct
 C&#x2212;N axes via cobalt-catalyzed enantioselective C&#x2212;H
 activation/annulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC05883J
_journal_year                    2025
_chemical_formula_moiety         'C37 H27 N3 O3 S, 2(C H2 Cl2)'
_chemical_formula_sum            'C39 H31 Cl4 N3 O3 S'
_chemical_formula_weight         763.53
_chemical_name_systematic        3aa
_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             2025-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.231(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.1261(17)
_cell_length_b                   9.8525(14)
_cell_length_c                   15.413(2)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    240.00
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.64
_cell_volume                     1840.0(4)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      240.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            60954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.049
_diffrn_reflns_theta_min         2.645
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6698
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1531 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.8983.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.822
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 2039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         8912
_refine_ls_number_restraints     161
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0757
_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^)+(0.1380P)^2^+0.4114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2286
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5696
_reflns_number_total             8912
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05883j2.cif
_cod_data_source_block           2
_cod_original_cell_volume        1840.1(5)
_cod_database_code               7135227
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.850
_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. Restrained distances
 Cl1-C5 \\sim Cl1A-C5A
 with sigma of 0.02
 C5-Cl8 \\sim C5A-Cl8A
 with sigma of 0.02
 Cl1-Cl8 \\sim Cl1A-Cl8A
 with sigma of 0.04
 Cl2-C2 \\sim Cl2A-C2A
 with sigma of 0.02
 Cl3-C2 \\sim Cl3A-C2A
 with sigma of 0.02
 Cl2-Cl3 \\sim Cl2A-Cl3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl8A \\sim C5A \\sim Cl1A \\sim Cl8 \\sim Cl1 \\sim C5: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C2A \\sim Cl2A \\sim Cl3A \\sim C2 \\sim Cl2 \\sim Cl3: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 Cl8, Cl1, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl8A, C5A, Cl1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2A, Cl2A, Cl3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl2, C2, Cl3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(Cl8A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(Cl8)=FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(Cl2A)=Sof(Cl3A)=1-FVAR(2)
 Sof(Cl2)=Sof(Cl3)=Sof(C2)=Sof(H2A)=Sof(H2B)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C5A(H5AA,H5AB), C2A(H2AA,H2AB)
6.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00O(H00O), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C018(H018), C019(H019), C01A(H01A), C01C(H01C)
6.c Idealised Me refined as rotating group:
 C01D(H01B,H01D,H01E)
;
_shelx_res_checksum              34191
_shelx_hkl_checksum              84208
_olex2_submission_special_instructions 'No special instructions were received'