Copper-catalyzed cascade double C3-indolations of 3-diazoindolin-2-imines with indoles: convenient access to 3,3-diaryl-2-iminoindoles.
Du, Zao; Xing, Yanpeng; Lu, Ping; Wang, Yanguang; Organic letters 17 (2015) 1192–1195; doi:10.1021/acs.orglett.5b00089

data_1554782
_publ_section_title
;
 Copper-catalyzed cascade double C3-indolations of 3-diazoindolin-2-imines
 with indoles: convenient access to 3,3-diaryl-2-iminoindoles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1192
_journal_page_last               1195
_journal_paper_doi               10.1021/acs.orglett.5b00089
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C34 H29 N5 O4 S'
_chemical_formula_sum            'C34 H29 N5 O4 S'
_chemical_formula_weight         603.68
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                72.931(7)
_cell_angle_beta                 74.564(6)
_cell_angle_gamma                84.268(6)
_cell_formula_units_Z            2
_cell_length_a                   9.7972(7)
_cell_length_b                   10.5090(8)
_cell_length_c                   15.4371(11)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      29.5816
_cell_measurement_theta_min      3.2996
_cell_volume                     1464.2(2)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
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      170.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0098591000
_diffrn_orient_matrix_UB_12      -0.0120366000
_diffrn_orient_matrix_UB_13      -0.0441567000
_diffrn_orient_matrix_UB_21      -0.0079019000
_diffrn_orient_matrix_UB_22      -0.0691890000
_diffrn_orient_matrix_UB_23      0.0222435000
_diffrn_orient_matrix_UB_31      -0.0740584000
_diffrn_orient_matrix_UB_32      0.0074713000
_diffrn_orient_matrix_UB_33      0.0042844000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9966
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.31
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92902
_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_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0413P)^2^+0.2849P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                4138
_reflns_number_total             5350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00089_si_002.cif
_cod_data_source_block           140708_duz_503_103
_cod_original_cell_volume        1464.16(18)
_cod_database_code               1554782
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
_reflns_odcompleteness_completeness 99.52
_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), C4(H4), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30), C31(H31), C32(H32),
  C33(H33)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C34(H34A,H34B,H34C)
;