DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline <i>N</i>-oxide.
Barik, Dinabandhu; Panigrahi, Pritishree; Manna, Supriya; Chakraborty, Nikita; Phouzder, Anushka; Patel, Bhisma K.; Chemical communications (Cambridge, England) 62 (2026) 3037–3040; doi:10.1039/d5cc06699a

data_7135541
_publ_section_title
;
 DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of
 quinoline <i>N</i>-oxide.
;
_journal_issue                   9
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3037
_journal_page_last               3040
_journal_paper_doi               10.1039/d5cc06699a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C17 H15 N O3 S'
_chemical_formula_sum            'C17 H15 N O3 S'
_chemical_formula_weight         313.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2025-06-18
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-11-19 deposited with the CCDC.	2026-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.765(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.510(10)
_cell_length_b                   8.002(3)
_cell_length_c                   18.352(8)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      3.11
_cell_volume                     3119(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33183
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        24.732
_diffrn_reflns_theta_max         24.732
_diffrn_reflns_theta_min         3.450
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6928
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.9297.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       Block
_exptl_crystal_F_000             1312
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0478P)^2^+1.7423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2301
_reflns_number_total             2584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06699a2.cif
_cod_data_source_block           dbb_p1_me_0ma_a
_cod_database_code               7135541
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16), C2(H2), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              56083
_shelx_hkl_checksum              66562
_shelx_fab_checksum              48733
_olex2_submission_special_instructions 'No special instructions were received'