Metal-free site-selective C‒H cyanoalkylation of 8-aminoquinoline and aniline-derived amides with azobisisobutyronitrile
Zhao, Mengfei; Qin, Zengxin; Zhang, Kaixin; Li, Jizhen; RSC Advances 11 (2021) 30719–30724; doi:10.1039/D1RA06013A

data_7243526
_publ_section_title
;
 Metal-free site-selective C--H cyanoalkylation of 8-aminoquinoline and
 aniline-derived amides with azobisisobutyronitrile
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              30719
_journal_page_last               30724
_journal_paper_doi               10.1039/D1RA06013A
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C20 H16 Br N3 O'
_chemical_formula_sum            'C20 H16 Br N3 O'
_chemical_formula_weight         394.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-06-22 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.1980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4703(3)
_cell_length_b                   14.2884(3)
_cell_length_c                   9.0192(2)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    180.0
_cell_measurement_theta_max      25.022
_cell_measurement_theta_min      2.686
_cell_volume                     1722.24(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      180.0
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22961
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.040
_diffrn_reflns_theta_min         2.087
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0443 after correction.
The Ratio of minimum to maximum transmission is 0.8261.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether/ethyl acetate'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0221
_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^)+(0.0262P)^2^+1.1080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2770
_reflns_number_total             3013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06013a2.cif
_cod_data_source_block           1
_cod_database_code               7243526
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.795
_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:
 N3(H3), C8(H8), C10(H10), C14(H14), C3(H3A), C7(H7), C15(H15), C2(H2), C9(H9),
  C19(H19)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              59081
_olex2_submission_special_instructions 'No special instructions were received'