Copper-catalyzed oxidative cyclization of 2-(1<i>H</i>-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to pyrrolo[1,2-<i>a</i>]quinoxalines.
An, Zhenyu; Miao, Man; Sun, Fengkai; Lan, Xiao-Bing; Yu, Jian-Qiang; Guo, Xiaoli; Zhang, Jian; Organic & biomolecular chemistry 22 (2024) 2370–2374; doi:10.1039/d3ob01934a

data_7159819
_publ_section_title
;
 Copper-catalyzed oxidative cyclization of
 2-(1<i>H</i>-pyrrol-1-yl)aniline and alkylsilyl peroxides: a route to
 pyrrolo[1,2-<i>a</i>]quinoxalines.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2370
_journal_page_last               2374
_journal_paper_doi               10.1039/d3ob01934a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H19 F N2 O'
_chemical_formula_sum            'C22 H19 F N2 O'
_chemical_formula_weight         346.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-08-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.3714(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.38752(8)
_cell_length_b                   13.87031(12)
_cell_length_c                   16.86229(17)
_cell_measurement_reflns_used    14676
_cell_measurement_temperature    149.98(10)
_cell_measurement_theta_max      76.7000
_cell_measurement_theta_min      3.1820
_cell_volume                     1687.71(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -26.00  30.00   0.50    0.05    --   47.57 -29.00 -65.00  112
  2  \w     -9.00  22.00   0.50    0.05    --   47.57 -19.00-120.00   62
  3  \w    -24.00  18.00   0.50    0.05    --   47.57 -19.00-150.00   84
  4  \w     37.00  62.00   0.50    0.05    --  107.75 -57.00 -60.00   50
  5  \w     35.00  61.00   0.50    0.05    --  107.75 -57.00 -90.00   52
  6  \w     72.00  97.00   0.50    0.05    --  107.75 -77.00-180.00   50
  7  \w     61.00  94.00   0.50    0.05    --  107.75-125.00-124.00   66
  8  \w   -105.00 -29.00   0.50    0.05    -- -100.00 125.00 -46.00  152
  9  \w    -59.00 -32.00   0.50    0.05    -- -100.00  57.00   0.00   54
 10  \w    -69.00 -43.00   0.50    0.05    -- -100.00  57.00 -90.00   52
 11  \w    -62.00 -28.00   0.50    0.05    -- -100.00  57.00-180.00   68
 12  \w   -136.00-105.00   0.50    0.05    -- -100.00 -29.00 -65.00   62
 13  \w   -118.00 -68.00   0.50    0.05    --  -47.57-145.00  68.00  100
 14  \w   -166.00-100.00   0.50    0.05    -- -100.00 -94.00 126.00  132
 15  \w    -13.00  50.00   0.50    0.05    --   47.57 -94.00 126.00  126
 16  \w    -25.00  17.00   0.50    0.05    --   47.57 -37.00   0.00   84
 17  \w    -27.00  -1.00   0.50    0.05    --   47.57 -19.00  30.00   52
 18  \w   -159.00-100.00   0.50    0.05    -- -100.00 -37.00 150.00  118
 19  \w   -105.00 -79.00   0.50    0.05    -- -100.00  77.00  30.00   52
 20  \w    -63.00 -37.00   0.50    0.05    -- -100.00  57.00 -30.00   52
 21  \w    -59.00 -29.00   0.50    0.05    -- -100.00  57.00  90.00   60
 22  \w     37.00  98.00   0.50    0.05    --  107.75 -94.00 126.00  122
 23  \w     77.00 102.00   0.50    0.05    --  107.75 -77.00 -30.00   50
 24  \w     37.00  69.00   0.50    0.05    --  107.75 -99.00  60.00   64
 25  \w     35.00  60.00   0.50    0.05    --  107.75 -57.00-180.00   50
 26  \w     80.00 105.00   0.50    0.05    --  107.75 -99.00  60.00   50
 27  \w     36.00  63.00   0.50    0.05    --  107.75 -57.00  60.00   54
 28  \w    -24.00   1.00   0.50    0.05    --   47.57 -94.00 127.00   50
 29  \w    -90.00 -24.00   0.50    0.05    --  -47.57 125.00 -60.00  132
 30  \w    -23.00  21.00   0.50    0.05    --   47.57 -19.00  90.00   88
 31  \w    -17.00  13.00   0.50    0.05    --   47.57 -19.00 -60.00   60
 32  \w     49.00  75.00   0.50    0.05    --   47.57 -94.00 127.00   52
 33  \w     -4.00  35.00   0.50    0.05    --   47.57 -37.00 150.00   78
 34  \w    -17.00  12.00   0.50    0.05    --   47.57 -19.00  60.00   58
 35  \w   -127.00 -95.00   0.50    0.05    -- -100.00 146.00  50.43   64
 36  \w   -140.00 -87.00   0.50    0.05    -- -100.00 -37.00-180.00  106
 37  \w   -108.00 -71.00   0.50    0.05    -- -100.00 111.00-116.12   74
 38  \w   -107.00 -70.00   0.50    0.05    -- -100.00 125.00  30.00   74
 39  \w    -87.00 -49.00   0.50    0.05    -- -100.00 125.00-120.00   76
 40  \w   -173.00-133.00   0.50    0.05    -- -100.00 -19.00  60.00   80
 41  \w   -169.00 -87.00   0.50    0.05    -- -100.00 -37.00   0.00  164
 42  \w    -68.00 -42.00   0.50    0.05    -- -100.00 111.00-116.12   52
 43  \w   -121.00 -87.00   0.50    0.05    -- -100.00 138.00-106.71   68
 44  \w   -126.00 -87.00   0.50    0.05    -- -100.00 -19.00  60.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0592542000
_diffrn_orient_matrix_UB_12      0.0407399000
_diffrn_orient_matrix_UB_13      -0.0866866000
_diffrn_orient_matrix_UB_21      0.2050675000
_diffrn_orient_matrix_UB_22      0.0107299000
_diffrn_orient_matrix_UB_23      -0.0045582000
_diffrn_orient_matrix_UB_31      -0.0021124000
_diffrn_orient_matrix_UB_32      -0.1027664000
_diffrn_orient_matrix_UB_33      -0.0348578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18850
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.478
_diffrn_reflns_theta_min         4.167
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0500P)^2^+0.4577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3215
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01934a2.cif
_cod_data_source_block           anzhenyu_0607_auto
_cod_depositor_comments          'Adding full bibliography for 7159819.cif.'
_cod_database_code               7159819
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              86293
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.600
_oxdiff_exptl_absorpt_empirical_full_min 0.364