Copper-Carbene-Triggered Electrophilic Cyclization of o-Hydroxyarylenaminones with 3-Diazoindolin-2-imines: Synthesis of 3-Indolyl-4 H-chromen-4-ones and Pyrido[2,3- b:6,5- b']diindoles.
Qian, Jing; Lin, Zhenwei; Wang, Zaibin; Peng, Zhixing; Wu, Li; Lu, Ping; Wang, Yanguang; The Journal of organic chemistry 84 (2019) 6395–6404; doi:10.1021/acs.joc.9b00755

data_4033589
_publ_section_title
;
 Copper-Carbene-Triggered Electrophilic Cyclization of
 o-Hydroxyarylenaminones with 3-Diazoindolin-2-imines: Synthesis of
 3-Indolyl-4 H-chromen-4-ones and Pyrido[2,3- b:6,5- b']diindoles.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6395
_journal_page_last               6404
_journal_paper_doi               10.1021/acs.joc.9b00755
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H14 N4'
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1669(14)
_cell_length_b                   6.0750(6)
_cell_length_c                   15.6269(17)
_cell_measurement_reflns_used    1044
_cell_measurement_temperature    155.0
_cell_measurement_theta_max      29.2001
_cell_measurement_theta_min      2.6015
_cell_volume                     1344.9(2)
_computing_cell_refinement
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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_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)'
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_diffrn_ambient_temperature      155.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -12.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   93.0000  104.0000 43

  2 omega  -66.00   23.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -77.0000   30.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0307786000
_diffrn_orient_matrix_UB_12      0.0699638000
_diffrn_orient_matrix_UB_13      0.0233059000
_diffrn_orient_matrix_UB_21      -0.0344928000
_diffrn_orient_matrix_UB_22      0.0846586000
_diffrn_orient_matrix_UB_23      -0.0009591000
_diffrn_orient_matrix_UB_31      -0.0192387000
_diffrn_orient_matrix_UB_32      -0.0397772000
_diffrn_orient_matrix_UB_33      0.0389100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
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_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0610P)^2^+0.6238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                965
_reflns_number_total             1239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00755_si_005.cif
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_cod_depositor_comments
'Adding full bibliography for 4033589--4033590.cif.'
_cod_database_code               4033589
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.958
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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), C2(H2), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              23768
_shelx_hkl_checksum              19513
_olex2_submission_special_instructions 'No special instructions were received'