Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems.
Al-Huniti, Mohammed H; Sullivan, Zachary B.; Stanley, Jarrod L.; Carson, James A.; Hyatt, I. F. Dempsey; Hairston, A. Christina; Croatt, Mitchell P.; The Journal of organic chemistry 82 (2017) 11772–11780; doi:10.1021/acs.joc.7b01608

data_4032763
_publ_section_title
;
 Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and
 Its Reactivity with Aromatic Systems.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11772
_journal_page_last               11780
_journal_paper_doi               10.1021/acs.joc.7b01608
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C12 H9 N O'
_chemical_formula_weight         183.20
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.8530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4869(6)
_cell_length_b                   5.5397(5)
_cell_length_c                   22.6003(18)
_cell_measurement_reflns_used    7949
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      3.61
_cell_volume                     937.25(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2 v2014.7'
_computing_publication_material  'Bruker APEX2 v2014.7'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17323
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_reduction_process narrow-frame
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.490
_diffrn_reflns_theta_min         3.606
_diffrn_source                   'fine-focus sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for absorption effects using the 
 multi-scan technique (SADABS). The ratio of minimum
 to maximum apparent transmission was 0.941.  The
 calculated minimum and maximum transmission
 coefficients (based on crystal size) are 0.974 and 0.988.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.7019
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0754P)^2^+0.1832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2575
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01608_si_003.cif
_cod_data_source_block           a29w2m_0m
_cod_depositor_comments          'Adding full bibliography for 4032763.cif.'
_cod_database_code               4032763
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.988
_computing_bruker_data_scaling   'SADABS V2014/5 (Bruker AXS)'
_shelx_res_checksum              5801
_shelx_hkl_checksum              5413