Copper-Catalyzed Regio- and Stereoselective Iodocyanation and Dicyanation of Alkynes with Cyanogen Iodide.
Sakata, Naoki; Sasakura, Kohei; Matsushita, Gaku; Okamoto, Kazuhiro; Ohe, Kouichi; Organic letters 19 (2017) 3422–3425; doi:10.1021/acs.orglett.7b01378

data_1547095
_publ_section_title
;
 Copper-Catalyzed Regio- and Stereoselective Iodocyanation and Dicyanation
 of Alkynes with Cyanogen Iodide.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3422
_journal_page_last               3425
_journal_paper_doi               10.1021/acs.orglett.7b01378
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C14 H10 I N'
_chemical_formula_sum            'C14 H10 I N'
_chemical_formula_weight         319.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.343(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.890(3)
_cell_length_b                   12.636(3)
_cell_length_c                   8.646(2)
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    143
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.13
_cell_volume                     1186.3(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9119
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         3.518
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.670
_exptl_absorpt_correction_T_max  0.586
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0586
_reflns_number_gt                2222
_reflns_number_total             2606
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol7b01378_si_004.cif
_cod_data_source_block           sakata007
_cod_database_code               1547095