Iron-Catalyzed Intramolecular C(sp(2))-N Cyclization of 1-(N-Arylpyrrol-2-yl)ethanone O-Acetyl Oximes toward Pyrrolo[1,2-a]quinoxaline Derivatives.
Zhang, Zhiguo; Li, Junlong; Zhang, Guisheng; Ma, Nana; Liu, Qingfeng; Liu, Tongxin; The Journal of organic chemistry 80 (2015) 6875–6884; doi:10.1021/acs.joc.5b00915

data_4031135
_publ_section_title
;
 Iron-Catalyzed Intramolecular C(sp(2))-N Cyclization of
 1-(N-Arylpyrrol-2-yl)ethanone O-Acetyl Oximes toward
 Pyrrolo[1,2-a]quinoxaline Derivatives.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6875
_journal_page_last               6884
_journal_paper_doi               10.1021/acs.joc.5b00915
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C12 H9 Cl N2'
_chemical_formula_sum            'C12 H9 Cl N2'
_chemical_formula_weight         216.66
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.167(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.0706(4)
_cell_length_b                   18.1822(13)
_cell_length_c                   13.7386(8)
_cell_measurement_reflns_used    849
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      68.6990
_cell_measurement_theta_min      4.0430
_cell_volume                     1014.14(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -18.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 35

  2 omega   15.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -150.0000 46

  3 omega   38.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -30.0000 36

  4 omega   34.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   37.0000  -60.0000 91

  5 omega   -8.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000  120.0000 90

  6 omega   52.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000   30.0000 25

  7 omega   75.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -30.0000 31

  8 omega   39.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 45

  9 omega   40.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 49

 10 omega   82.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 27

 11 omega   55.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 34

 12 omega   40.00   85.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 45

 13 omega  111.00  177.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 66

 14 omega   54.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 42

 15 omega   39.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  150.0000 36

 16 omega   41.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 41

 17 omega   41.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 48

 18 omega  -44.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000   30.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0162881000
_diffrn_orient_matrix_UB_12      0.0599864000
_diffrn_orient_matrix_UB_13      0.0793241000
_diffrn_orient_matrix_UB_21      -0.0717880000
_diffrn_orient_matrix_UB_22      0.0590655000
_diffrn_orient_matrix_UB_23      -0.0789875000
_diffrn_orient_matrix_UB_31      -0.3725423000
_diffrn_orient_matrix_UB_32      -0.0089642000
_diffrn_orient_matrix_UB_33      0.0104632000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3461
_diffrn_reflns_theta_full        67.02
_diffrn_reflns_theta_max         67.02
_diffrn_reflns_theta_min         4.04
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0861P)^2^+0.1228P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1641
_reflns_number_gt                1360
_reflns_number_total             1812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00915_si_002.cif
_cod_data_source_block           20150106
_cod_depositor_comments          'Adding full bibliography for 4031135.cif.'
_cod_original_cell_volume        1014.14(13)
_cod_database_code               4031135
_chemical_oxdiff_formula         C20H20N4O4Cl2
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_olex2_submission_special_instructions 'No special instructions were received'