Cu(OAc)<sub>2</sub>-Promoted Ortho C(sp<sup>2</sup>)-H Amidation of 8-Aminoquinoline Benzamide with Acyl Azide: Selective Formation of Aroyl or Acetyl Amide Based on Catalyst Loading.
Ghosh, Tubai; Maity, Pintu; Ranu, Brindaban C.; The Journal of organic chemistry 83 (2018) 11758–11767; doi:10.1021/acs.joc.8b01654

data_4035219
_publ_section_title
;
 Cu(OAc)<sub>2</sub>-Promoted Ortho C(sp<sup>2</sup>)-H Amidation of
 8-Aminoquinoline Benzamide with Acyl Azide: Selective Formation of Aroyl
 or Acetyl Amide Based on Catalyst Loading.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11758
_journal_page_last               11767
_journal_paper_doi               10.1021/acs.joc.8b01654
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H13 N3 O2 S'
_chemical_formula_sum            'C16 H13 N3 O2 S'
_chemical_formula_weight         311.35
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                88.210(4)
_cell_angle_beta                 86.511(4)
_cell_angle_gamma                79.953(4)
_cell_formula_units_Z            2
_cell_length_a                   7.2860(8)
_cell_length_b                   8.3926(10)
_cell_length_c                   12.1427(13)
_cell_measurement_reflns_used    3009
_cell_measurement_temperature    132(2)
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.47
_cell_volume                     729.61(14)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      132.55
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0463
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7575
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.015
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_min         2.955
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1242 before and 0.0620 after correction.
The Ratio of minimum to maximum transmission is 0.8168.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             324
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0443P)^2^+0.1916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1994
_reflns_number_total             2538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01654_si_003.cif
_cod_data_source_block           mo_broc250917_0m
_cod_database_code               4035219
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), N005(H005), C00B(H00B), C00C(H00C), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00D,H00F)
;
_shelx_res_checksum              4273
_shelx_hkl_checksum              45297
_olex2_submission_special_instructions 'No special instructions were received'