DMSO/<i>t</i>BuONa/O<sub>2</sub>-mediated efficient syntheses of diverse quinoxalines through α-imino radicals.
Zhang, Chihong; Zhang, Zhen; Wang, Deliang; Wang, Wenkun; Jin, Bo; Wen, Tao; Ye, Lihua; Chen, Zhong-Ning; Cai, Hu; Chemical communications (Cambridge, England) 59 (2023) 5217–5220; doi:10.1039/d3cc00086a

data_7131490
_publ_section_title
;
 DMSO/<i>t</i>BuONa/O<sub>2</sub>-mediated efficient syntheses of diverse
 quinoxalines through &#x3b1;-imino radicals.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5217
_journal_page_last               5220
_journal_paper_doi               10.1039/d3cc00086a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C14 H9 Cl N2'
_chemical_formula_sum            'C14 H9 Cl N2'
_chemical_formula_weight         240.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-04
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-04 deposited with the CCDC.	2023-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.509(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5545(14)
_cell_length_b                   4.7731(7)
_cell_length_c                   12.5151(18)
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      3.05
_cell_volume                     554.96(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_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  0.0170
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3399
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.703
_diffrn_reflns_theta_min         3.054
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9253.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             248
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0448P)^2^+0.0326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.721
_reflns_number_gt                1989
_reflns_number_total             2250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00086a2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7131490.cif.'
_cod_database_code               7131490
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_shelx_res_checksum              98930
_shelx_hkl_checksum              99972
_olex2_submission_special_instructions 'No special instructions were received'