Unusual C-2 selectivity of Grignard additions to <i>N</i>-Boc-protected isatin 3-imines.
Plakas, Alexandra Mary; Butsi, Kamogelo Rosinah; Lala, Sahil; van Zyl, Robyn Lynne; Fernandes, Manuel Antonio; Ntsimango, Songeziwe; Bode, Moira Leanne; Rousseau, Amanda Louise; Organic & biomolecular chemistry 24 (2026) 1672–1677; doi:10.1039/d5ob01909e

data_7160941
_publ_section_title
;
 Unusual C-2 selectivity of Grignard additions to <i>N</i>-Boc-protected
 isatin 3-imines.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1672
_journal_page_last               1677
_journal_paper_doi               10.1039/d5ob01909e
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C30 H27 Cl N2 O2'
_chemical_formula_sum            'C30 H27 Cl N2 O2'
_chemical_formula_weight         482.98
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-12-04 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                107.5160(10)
_cell_angle_beta                 95.1060(10)
_cell_angle_gamma                103.4500(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8224(3)
_cell_length_b                   10.4896(3)
_cell_length_c                   12.9397(4)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      2.22
_cell_volume                     1218.22(6)
_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      173.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            45607
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.578
_diffrn_reflns_theta_min         2.116
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.8733.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0393P)^2^+0.4484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5211
_reflns_number_total             6119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01909e2.cif
_cod_data_source_block           Compound_2c_24mb_ar2_alex1_opus
_cod_depositor_comments
'Adding full bibliography for 7160941--7160942.cif.'
_cod_database_code               7160941
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.956
_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:
 C9(H9A,H9B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29),
  C30(H30)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              65185
_shelx_hkl_checksum              97484
_olex2_submission_special_instructions 'No special instructions were received'