Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and Aromatic Compounds
Matthew R. Smith; Alexander J. Blake; Christopher J. Hayes; Malcolm F. G. Stevens; Christopher J. Moody; Journal of Organic Chemistry 74 (2009) 9372–9380; doi:10.1021/jo902165w

data_4025117
_publ_section_title
;
Carbene Reactivity of 4-Diazo-4H-imidazoles toward Nucleophiles and
Aromatic Compounds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9372
_journal_page_last               9380
_journal_paper_doi               10.1021/jo902165w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C23 H12 F6 N2 O2'
_chemical_formula_sum            'C23 H12 F6 N2 O2'
_chemical_formula_weight         462.35
_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
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                114.378(2)
_cell_angle_beta                 93.584(2)
_cell_angle_gamma                97.782(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4982(7)
_cell_length_b                   10.9169(9)
_cell_length_c                   11.4853(10)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.15
_cell_volume                     953.3(2)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.101
_diffrn_reflns_av_sigmaI/netI    0.084
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8488
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.08
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.046P)^2^+0.135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.117
_refine_ls_wR_factor_ref         0.121
_reflns_number_gt                3782
_reflns_number_total             4290
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo902165w_si_002.cif
_cod_data_source_block           phimac
_cod_database_code               4025117