Hypervalent iodine-mediated highly mono- and di-selective etherification of 8-aminoquinolines at the C5 and C6 positions.
Qu, Hongen; Liang, Pei; Shi, Qiu; Xiao, Shangqing; Huang, Panpan; Wang, Hengshan; Zhou, Zhonggao; Liu, Liangxian; Organic & biomolecular chemistry 23 (2025) 10656–10661; doi:10.1039/d5ob01378j

data_7160842
_publ_section_title
;
 Hypervalent iodine-mediated highly mono- and di-selective etherification
 of 8-aminoquinolines at the C5 and C6 positions.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10656
_journal_page_last               10661
_journal_paper_doi               10.1039/d5ob01378j
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         '3(C18 N2 O3), C18 N3 O2'
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-03-18 deposited with the CCDC.	2025-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.888(2)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   7.5494(14)
_cell_length_b                   24.117(5)
_cell_length_c                   8.3213(16)
_cell_measurement_reflns_used    3655
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.901
_cell_measurement_theta_min      3.527
_cell_volume                     1511.6(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.910
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8726
_diffrn_reflns_point_group_measured_fraction_full 0.590
_diffrn_reflns_point_group_measured_fraction_max 0.565
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.393
_diffrn_reflns_theta_min         3.527
_exptl_absorpt_coefficient_mu    0.004
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0841 before and 0.0346 after correction.
The Ratio of minimum to maximum transmission is 0.8904.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    0.047
_exptl_crystal_F_000             22
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         7742
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.1040
_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^)+(0.1780P)^2^+1.5570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2913
_refine_ls_wR_factor_ref         0.3084
_reflns_Friedel_coverage         0.241
_reflns_Friedel_fraction_full    0.238
_reflns_Friedel_fraction_max     0.219
_reflns_number_gt                6266
_reflns_number_total             7742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01378j1.cif
_cod_data_source_block           dzf67b_0m
_cod_depositor_comments          'Adding full bibliography for 7160842.cif.'
_cod_database_code               7160842
_olex2_refinement_description
;
;
_shelx_res_checksum              33979
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'