Selective Access to 3-Cyano-1H-indoles, 9H-Pyrimido[4,5-b]indoles, or 9H-Pyrido[2,3-b]indoles through Copper-Catalyzed One-Pot Multicomponent Cascade Reactions.
Li, Bin; Guo, Shenghai; Zhang, Ju; Zhang, Xinying; Fan, Xuesen; The Journal of organic chemistry 80 (2015) 5444–5456; doi:10.1021/acs.joc.5b00239

data_4031003
_publ_section_title
;
 Selective Access to 3-Cyano-1H-indoles, 9H-Pyrimido[4,5-b]indoles, or
 9H-Pyrido[2,3-b]indoles through Copper-Catalyzed One-Pot Multicomponent
 Cascade Reactions.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5444
_journal_page_last               5456
_journal_paper_doi               10.1021/acs.joc.5b00239
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39
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_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                64.99(3)
_cell_angle_beta                 67.67(3)
_cell_angle_gamma                88.86(3)
_cell_formula_units_Z            2
_cell_length_a                   9.982(2)
_cell_length_b                   10.135(2)
_cell_length_c                   11.350(2)
_cell_measurement_temperature    293(2)
_cell_volume                     948.9(5)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9093
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_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.7886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.4
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_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.235
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3277
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_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1814P)^2^+0.1755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2331
_refine_ls_wR_factor_ref         0.2777
_reflns_number_gt                2701
_reflns_number_total             3277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00239_si_002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031002--4031003.cif.
;
_cod_original_cell_volume        948.9(3)
_cod_original_sg_symbol_Hall     -p1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4031003