Multiple Transformations of 2-Alkynyl-1,8-bis(dimethylamino)naphthalenes into Benzo[g]indoles. Pd/Cu-Dependent Switching of the Electrophilic and Nucleophilic Sites in Acetylenic Bond and a Puzzle of Porcelain Catalysis.
Filatova, Ekaterina A.; Pozharskii, Alexander F.; Gulevskaya, Anna V.; Ozeryanskii, Valery A.; The Journal of organic chemistry 80 (2015) 872–881; doi:10.1021/jo502363t

data_4030384
_publ_section_title
;
 Multiple Transformations of 2-Alkynyl-1,8-bis(dimethylamino)naphthalenes
 into Benzo[g]indoles. Pd/Cu-Dependent Switching of the Electrophilic and
 Nucleophilic Sites in Acetylenic Bond and a Puzzle of Porcelain
 Catalysis.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              872
_journal_page_last               881
_journal_paper_doi               10.1021/jo502363t
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C37 H28 N2'
_chemical_formula_sum            'C37 H28 N2'
_chemical_formula_weight         500.61
_space_group_IT_number           2
_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                100.749(2)
_cell_angle_beta                 101.079(2)
_cell_angle_gamma                90.815(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2664(9)
_cell_length_b                   14.6024(14)
_cell_length_c                   20.5848(19)
_cell_measurement_reflns_used    2698
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      2.24
_cell_volume                     2681.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_sigmaI/netI    0.1426
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            33661
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     709
_refine_ls_number_reflns         14264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0437P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                6896
_reflns_number_total             14264
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo502363t_si_003.cif
_cod_data_source_block           s01
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--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 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030382--4030385.cif.
;
_cod_database_code               4030384