Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile.
Wen, Chunxia; Zhong, Ronglin; Qin, Zengxin; Zhao, Mengfei; Li, Jizhen; Chemical communications (Cambridge, England) 56 (2020) 9529–9532; doi:10.1039/d0cc00014k

data_7126852
_publ_section_title
;
 Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of
 8-aminoquinolines with azobisisobutyronitrile.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9529
_journal_page_last               9532
_journal_paper_doi               10.1039/d0cc00014k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C21 H19 N3 O2'
_chemical_formula_weight         345.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-08-13 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4892(11)
_cell_length_b                   7.3635(6)
_cell_length_c                   18.9497(17)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2
_cell_volume                     1742.7(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean graphite
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9497
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         1.631
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1150 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0500P)^2^+0.0648P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2929
_reflns_number_total             3459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00014k2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7126852.cif.'
_cod_database_code               7126852
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              76690