Photoredox-catalysed chlorination of quinoxalin-2(1H)-ones enabled by using CHCl3 as chlorine source
Yang, Hua; Wu, Mei-Chun; Li, Ming-Zhi; Chen, Jia-Yi; Xiao, Jun-An; Xiang, Haoyue; Chen, Kai; Chemical Communications  (2022) –; doi:10.1039/D2CC04520F

data_7130752
_publ_section_title
;
 Photoredox-catalysed chlorination of quinoxalin-2(1H)-ones enabled by
 using CHCl3 as chlorine source
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04520F
_journal_year                    2022
_chemical_formula_moiety         'C10 H9 Cl N2 O'
_chemical_formula_sum            'C10 H9 Cl N2 O'
_chemical_formula_weight         208.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-28 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.8516(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3980(3)
_cell_length_b                   10.9637(4)
_cell_length_c                   11.9743(4)
_cell_measurement_reflns_used    5246
_cell_measurement_temperature    156(2)
_cell_measurement_theta_max      56.954
_cell_measurement_theta_min      5.646
_cell_volume                     950.53(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      156.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6184
_diffrn_reflns_theta_full        56.99
_diffrn_reflns_theta_max         56.99
_diffrn_reflns_theta_min         5.65
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.139
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1542 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.7499.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BAR
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0575P)^2^+0.3643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1788
_reflns_number_total             1920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc04520f2.cif
_cod_data_source_block           20220627_2_0m
_cod_depositor_comments
;

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C40 H36 Cl4 N8 O4'
_cod_original_formula_weight         834.57
_cod_original_formula_moiety         '4(C10 H9 Cl N2 O)'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        950.52(6)
_cod_database_code               7130752
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'