N-Methyl Transfer Induced Copper-Mediated Oxidative Diamination of Alkynes.
Ho, Hon Eong; Oniwa, Kazuaki; Yamamoto, Yoshinori; Jin, Tienan; Organic letters 18 (2016) 2487–2490; doi:10.1021/acs.orglett.6b01067

data_1543270
_publ_section_title
;
 N-Methyl Transfer Induced Copper-Mediated Oxidative Diamination of
 Alkynes.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2487
_journal_page_last               2490
_journal_paper_doi               10.1021/acs.orglett.6b01067
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_chemical_name_common            5,10-dimethyl-5,10-dihydroindolo[3,2-b]indole
_chemical_name_systematic        ;Indoloindole;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 113.4303(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8715(6)
_cell_length_b                   5.5938(2)
_cell_length_c                   17.2693(10)
_cell_measurement_reflns_used    126
_cell_measurement_temperature    300
_cell_measurement_theta_max      54.91
_cell_measurement_theta_min      8.91
_cell_volume                     1229.51(10)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAPID-S'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11442
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.201
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.030(6)
_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   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0754
_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
'w=1/[\s^2^(Fo^2^)+(0.1039P)^2^+0.2359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1908
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2086
_reflns_number_total             2819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01067_si_002.cif
_cod_data_source_block           Indoloindole
_cod_depositor_comments          'Adding full bibliography for 1543270.cif.'
_cod_database_code               1543270
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2014-3
_shelx_res_checksum              63474
_shelx_hkl_checksum              65069