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_7158477
_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         'C29 H22 N2 S'
_chemical_formula_sum            'C29 H22 N2 S'
_chemical_formula_weight         430.54
_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     dual
_audit_creation_date             2021-09-09
_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                86.3840(10)
_cell_angle_beta                 78.9380(10)
_cell_angle_gamma                86.4020(10)
_cell_formula_units_Z            4
_cell_length_a                   7.5089(2)
_cell_length_b                   15.5665(3)
_cell_length_c                   18.8172(4)
_cell_measurement_reflns_used    6197
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      2.40
_cell_volume                     2151.44(8)
_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      173.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24401
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.291
_diffrn_reflns_theta_min         2.396
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.476
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.8843.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         7795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0615P)^2^+0.7132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1508
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5529
_reflns_number_total             7795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02248b2.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7158476--7158478.cif.'
_cod_original_cell_volume        2151.45(8)
_cod_database_code               7158477
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.843
_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:
 C10(H10), C56(H56), C39(H39), C57(H57), C42(H42), C51(H51), C53(H53),
 C33(H33), C28(H28), C35(H35), C24(H24), C9(H9), C38(H38), C22(H22), C45(H45),
 C27(H27), C4(H4), C48(H48), C16(H16), C25(H25), C36(H36), C50(H50), C32(H32),
 C13(H13), C54(H54), C21(H21), C49(H49), C3(H3), C19(H19), C6(H6), C20(H20),
 C7(H7)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C1(H1A,H1B,H1C), C58(H58A,H58B,H58C)
;
_shelx_res_checksum              33091
_olex2_submission_special_instructions 'No special instructions were received'