Copper(II)-catalyzed, site-selective C(sp)<sup>2</sup>-H amination using 8-aminoimidazo[1,2-<i>a</i>]pyridine (8-AIP) as a directing group.
Hajra, Arun Kumar; Ghosh, Prasanjit; Roy, Chandrayee; Kundu, Mrinalkanti; Ghosh, Shibaji; Das, Sajal; Organic & biomolecular chemistry 22 (2024) 6617–6630; doi:10.1039/d4ob01008f

data_7160059
_publ_section_title
;
 Copper(II)-catalyzed, site-selective C(sp)<sup>2</sup>-H amination using
 8-aminoimidazo[1,2-<i>a</i>]pyridine (8-AIP) as a directing group.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6617
_journal_page_last               6630
_journal_paper_doi               10.1039/d4ob01008f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H17 Br N4 O2'
_chemical_formula_sum            'C18 H17 Br N4 O2'
_chemical_formula_weight         401.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-24 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2070(7)
_cell_length_b                   12.3855(8)
_cell_length_c                   13.5520(7)
_cell_measurement_reflns_used    9793
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.823
_cell_measurement_theta_min      2.498
_cell_volume                     1713.23(18)
_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      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            145680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.441
_diffrn_reflns_theta_min         2.228
_exptl_absorpt_coefficient_mu    2.419
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0879 before and 0.0765 after correction. The Ratio of minimum to maximum transmission is 0.8417. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 1874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         8854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0497P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5128
_reflns_number_total             8854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01008f2.cif
_cod_data_source_block           16906_83_1_p2_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160059.cif.'
_cod_database_code               7160059
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.531
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              93700
_olex2_submission_special_instructions 'No special instructions were received'