Site-selective C(sp<sup>3</sup>)-H amination of (het)aryl acetic acid derivatives under copper(II) catalysis.
Hajra, Arun Kumar; Ghosh, Prasanjit; Roy, Chandreyee; Kundu, Mrinalkanti; Das, Sajal; Organic & biomolecular chemistry 23 (2025) 7345–7355; doi:10.1039/d5ob00787a

data_7160644
_publ_section_title
;
 Site-selective C(sp<sup>3</sup>)-H amination of (het)aryl acetic acid
 derivatives under copper(II) catalysis.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7345
_journal_page_last               7355
_journal_paper_doi               10.1039/d5ob00787a
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C20 H22 N4 O'
_chemical_formula_sum            'C20 H22 N4 O'
_chemical_formula_weight         334.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-02-19 deposited with the CCDC.	2025-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.287(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6746(6)
_cell_length_b                   11.1003(6)
_cell_length_c                   13.6168(7)
_cell_measurement_reflns_used    9574
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      28.596
_cell_measurement_theta_min      2.380
_cell_volume                     1741.49(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      278
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            126285
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_min         2.135
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0967 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.9248. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0790P)^2^+0.3072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4196
_reflns_number_total             5334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00787a2.cif
_cod_data_source_block           20076_73_1_p_0ma_a
_cod_depositor_comments          'Adding full bibliography for 7160644.cif.'
_cod_database_code               7160644
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              62900
_olex2_submission_special_instructions 'No special instructions were received'