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_4033309
_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            'C14 H11 N'
_chemical_formula_weight         193.24
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1837(14)
_cell_length_b                   7.2636(8)
_cell_length_c                   10.4068(11)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      3.66
_cell_volume                     996.57(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2'
_computing_publication_material  'Bruker APEX2'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       '\f and \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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13888
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9785
_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 0.951.  The
 calculated minimum and maximum transmission
 coefficients (based on crystal size) are 0.979 and 0.995. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.006(3)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0687P)^2^+0.2534P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                1383
_reflns_number_total             1563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01608_si_002.cif
_cod_data_source_block           a88t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/current/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4033309
_computing.bruker_data_scaling   'SADABS V2008/1 (Sheldrick)'