Construction of Pyrrolo[1,2-a]indoles via Cobalt(III)-Catalyzed Enaminylation of 1-(Pyrimidin-2-yl)-1H-indoles with Ketenimines and Subsequent Base-Promoted Cyclization.
Zhou, Xiaorong; Fan, Zili; Zhang, Zhiyin; Lu, Ping; Wang, Yanguang; Organic letters 18 (2016) 4706–4709; doi:10.1021/acs.orglett.6b02353

data_1544508
_publ_section_title
;
 Construction of Pyrrolo[1,2-a]indoles via Cobalt(III)-Catalyzed
 Enaminylation of 1-(Pyrimidin-2-yl)-1H-indoles with Ketenimines and
 Subsequent Base-Promoted Cyclization.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4706
_journal_page_last               4709
_journal_paper_doi               10.1021/acs.orglett.6b02353
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C29 H23 Cl N4 O2'
_chemical_formula_sum            'C29 H23 Cl N4 O2'
_chemical_formula_weight         494.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                63.655(8)
_cell_angle_beta                 83.383(6)
_cell_angle_gamma                68.088(7)
_cell_formula_units_Z            2
_cell_length_a                   11.0894(7)
_cell_length_b                   11.1837(9)
_cell_length_c                   11.8059(9)
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    171.1
_cell_measurement_theta_max      29.2986
_cell_measurement_theta_min      2.8435
_cell_volume                     1215.08(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      171.1
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0649981000
_diffrn_orient_matrix_UB_12      0.0411689000
_diffrn_orient_matrix_UB_13      0.0053428000
_diffrn_orient_matrix_UB_21      0.0088968000
_diffrn_orient_matrix_UB_22      0.0629746000
_diffrn_orient_matrix_UB_23      -0.0464529000
_diffrn_orient_matrix_UB_31      -0.0216029000
_diffrn_orient_matrix_UB_32      -0.0101208000
_diffrn_orient_matrix_UB_33      -0.0482178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7646
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.85
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.3927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0946
_reflns_number_gt                3484
_reflns_number_total             4437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02353_si_002.cif
_cod_data_source_block           151222_zxr454_054b_1
_cod_original_cell_volume        1215.08(16)
_cod_database_code               1544508
_chemical_oxdiff_formula         'c10 h10 n2 o8 Cl1'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 H4-N4
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4A), C5(H5), C7(H7), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C27(H27), C28(H28),
  C29(H29)
3.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;