Pd-Catalyzed direct C-H arylation of pyrrolo[1,2-<i>a</i>]quinoxalines.
Hao, Di; Yang, Zhen; Liu, Yali; Li, Yang; Li, Chuntian; Gu, Yanlong; Vaccaro, Luigi; Liu, Jichang; Liu, Ping; Organic & biomolecular chemistry 20 (2022) 847–851; doi:10.1039/d1ob02248b

data_7158476
_publ_section_title
;
 Pd-Catalyzed direct C-H arylation of pyrrolo[1,2-<i>a</i>]quinoxalines.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              847
_journal_page_last               851
_journal_paper_doi               10.1039/d1ob02248b
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C25 H20 N2'
_chemical_formula_sum            'C25 H20 N2'
_chemical_formula_weight         348.43
_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             2020-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-24 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8016(2)
_cell_length_b                   10.2699(2)
_cell_length_c                   18.6233(4)
_cell_measurement_reflns_used    7144
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.28
_cell_volume                     1834.49(7)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22818
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.276
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0487P)^2^+0.7952P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3219
_reflns_number_total             3882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02248b2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7158476--7158478.cif.'
_cod_database_code               7158476
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_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), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              16079
_olex2_submission_special_instructions 'No special instructions were received'