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_1544033
_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         'C27 H22 Cl N3 O2'
_chemical_formula_sum            'C27 H22 Cl N3 O2'
_chemical_formula_weight         455.93
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-05
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.449(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.5227(19)
_cell_length_b                   13.0043(8)
_cell_length_c                   16.6637(11)
_cell_measurement_reflns_used    1988
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3969
_cell_measurement_theta_min      3.2152
_cell_volume                     4704.3(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_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)
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_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      293.15
_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      0.0246116000
_diffrn_orient_matrix_UB_12      0.0039220000
_diffrn_orient_matrix_UB_13      -0.0189839000
_diffrn_orient_matrix_UB_21      -0.0208056000
_diffrn_orient_matrix_UB_22      -0.0095107000
_diffrn_orient_matrix_UB_23      -0.0394632000
_diffrn_orient_matrix_UB_31      -0.0054922000
_diffrn_orient_matrix_UB_32      0.0535492000
_diffrn_orient_matrix_UB_33      -0.0056075000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9573
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95153
_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    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0652P)^2^+1.4522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                2798
_reflns_number_total             4309
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02353_si_003.cif
_cod_data_source_block           160705_zxr454_066d
_cod_depositor_comments
'Adding full bibliography for 1544033--1544034.cif.'
_cod_database_code               1544033
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_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,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C27A-C26
 1.53 with sigma of 0.02
 C26-C27
 1.53 with sigma of 0.02
3. Others
 Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=1-FVAR(1)
 Sof(H26B)=Sof(H26A)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C26(H26B,H26A), C26(H26C,H26D)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C1(H1), C2(H2), C3(H3A), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
4.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C27A(H27D,H27E,H27F)
;