Silver-free, palladium-catalyzed arylation of pyrrolo[1,2-<i>a</i>]quinoxaline C-H bonds with aryl bromides.
Ong, Khanh Thi Ngoc; Nguyen, Ha Thi Thu; Nguyen, Anh Thai; Luu, Vu Huynh; Tran, Dat Huy; Ca, Thuy Thi; Doan, Tan Le Hoang; Nguyen, Hung Huy; Nguyen, Tung Thanh; Organic & biomolecular chemistry 23 (2025) 3562–3566; doi:10.1039/d5ob00023h

data_7160424
_publ_section_title
;
 Silver-free, palladium-catalyzed arylation of
 pyrrolo[1,2-<i>a</i>]quinoxaline C-H bonds with aryl bromides.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3562
_journal_page_last               3566
_journal_paper_doi               10.1039/d5ob00023h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H15 N3 O2'
_chemical_formula_sum            'C23 H15 N3 O2'
_chemical_formula_weight         365.38
_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     dual
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-05 deposited with the CCDC.	2025-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3695(2)
_cell_length_b                   7.37850(10)
_cell_length_c                   18.8523(4)
_cell_measurement_reflns_used    7990
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      65.034
_cell_measurement_theta_min      4.372
_cell_volume                     1718.71(5)
_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  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22227
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.046
_diffrn_reflns_theta_max         65.046
_diffrn_reflns_theta_min         4.186
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.8921.
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    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0304P)^2^+2.4829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2075
_reflns_number_total             2932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00023h2.cif
_cod_data_source_block           apqt2_0m
_cod_depositor_comments          'Adding full bibliography for 7160424.cif.'
_cod_database_code               7160424
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.896
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
;
_shelx_res_checksum              25397
_olex2_submission_special_instructions 'No special instructions were received'