Electro-oxidation induced O–S cross-coupling of quinoxalinones with sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines
Shi, Shi-Hui; Wei, Jian; Liang, Chun-Miao; Bai, Huan; Zhu, Hai-Tao; Zhang, Yantu; Fu, Feng; Chemical Communications  (2022) –; doi:10.1039/D2CC04524A

data_7130880
_publ_section_title
;
 Electro-oxidation induced O--S cross-coupling of quinoxalinones with
 sodium sulfinates for synthesizing 2-sulfonyloxylated quinoxalines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04524A
_journal_year                    2022
_chemical_formula_moiety         'C15 H10 Br2 N2 O3 S'
_chemical_formula_sum            'C15 H10 Br2 N2 O3 S'
_chemical_formula_weight         458.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-25 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                88.586(4)
_cell_angle_beta                 79.678(3)
_cell_angle_gamma                84.807(4)
_cell_formula_units_Z            2
_cell_length_a                   6.2412(7)
_cell_length_b                   8.1065(9)
_cell_length_c                   16.0274(18)
_cell_measurement_reflns_used    8951
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.492
_cell_measurement_theta_min      3.331
_cell_volume                     794.47(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16685
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         3.331
_exptl_absorpt_coefficient_mu    5.248
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0883 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.7434.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+0.3873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2989
_reflns_number_total             3649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04524a2.cif
_cod_data_source_block           111
_cod_database_code               7130880
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.405
_shelx_estimated_absorpt_t_min   0.254
_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:
 C3(H3), C6(H6), C4(H4), C15(H15), C9(H9), C12(H12), C7(H7)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              41599
_shelx_hkl_checksum              73444
_olex2_submission_special_instructions 'No special instructions were received'