KHMDS mediated ring-opening/reconstruction of anthranils with arylacetonitriles: synthesis of multisubstituted 2-aminoquinoline N-oxides
Jat, Ram Singh; Singh, Gautami; Bhanuchandra, M.; New Journal of Chemistry 48 (2024) 8574–8577; doi:10.1039/D4NJ00311J

data_7063182
_publ_section_title
;
 KHMDS mediated ring-opening/reconstruction of anthranils with
 arylacetonitriles: synthesis of multisubstituted 2-aminoquinoline
 N-oxides
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8574
_journal_page_last               8577
_journal_paper_doi               10.1039/D4NJ00311J
_journal_volume                  48
_journal_year                    2024
_chemical_formula_sum            'C21 H15 Cl N2 O'
_chemical_formula_weight         346.80
_chemical_name_systematic        3ia
_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_method           SHELXL-2019/3
_audit_update_record
;
2024-03-01 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2658(2)
_cell_length_b                   7.9217(2)
_cell_length_c                   29.7691(10)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.89
_cell_volume                     1713.43(9)
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            52147
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.112
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0373P)^2^+0.4997P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3707
_reflns_number_total             3787
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj00311j2.cif
_cod_data_source_block           compound3ia
_cod_depositor_comments
'Adding full bibliography for 7063181--7063182.cif.'
_cod_database_code               7063182
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              98625
_shelx_hkl_checksum              85947