Electrochemical cascade sequences for remote C7–H bond thiocyanation of quinoxalin-2(1H)-ones with ammonium thiocyanate
Maity, Rajib; Bankura, Abhijit; Das, Indrajit; Green Chemistry 25 (2023) 7774–7781; doi:10.1039/D3GC02153J

data_7247248
_publ_section_title
;
 Electrochemical cascade sequences for remote C7--H bond thiocyanation of
 quinoxalin-2(1H)-ones with ammonium thiocyanate
;
_journal_issue                   19
_journal_name_full               'Green Chemistry'
_journal_page_first              7774
_journal_page_last               7781
_journal_paper_doi               10.1039/D3GC02153J
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C10 H9 N3 O S'
_chemical_formula_sum            'C10 H9 N3 O S'
_chemical_formula_weight         219.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-30 deposited with the CCDC.	2023-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.896(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2596(7)
_cell_length_b                   11.1219(9)
_cell_length_c                   11.4922(9)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.36
_cell_measurement_theta_min      5.73
_cell_volume                     986.27(14)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2014/5(Sheldrick 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19902
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.513
_diffrn_reflns_theta_min         3.975
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms Diamond'
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1358 before and 0.0856 after correction.
The Ratio of minimum to maximum transmission is 0.6654.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0596P)^2^+0.3586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.832
_reflns_Friedel_fraction_max     0.818
_reflns_number_gt                3084
_reflns_number_total             3260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc02153j2.cif
_cod_data_source_block           rm_5_147ab_0m_b
_cod_depositor_comments
'Adding full bibliography for 7247248--7247249.cif.'
_cod_database_code               7247248
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.613
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C6(H6), C8(H8), N5(H5A), C14(H14), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              34623
_shelx_hkl_checksum              61570
_olex2_submission_special_instructions 'No special instructions were received'