Synthesis of 4- and 4,5-Functionalized Imidazol-2-ylidenes from a Single 4,5-Unsubstituted Imidazol-2-ylidene
Daniel Mendoza-Espinosa; Bruno Donnadieu; Guy Bertrand; Journal of the American Chemical Society 132 (2010) 7264–7265; doi:10.1021/ja102639a

data_4102484
_publ_section_title
;
 Synthesis of 4- and 4,5-Functionalized Imidazol-2-ylidenes from a Single
 4,5-Unsubstituted Imidazol-2-ylidene
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7264
_journal_page_last               7265
_journal_paper_doi               10.1021/ja102639a
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C34 H39 N2 O'
_chemical_formula_weight         491.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.269(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.148(3)
_cell_length_b                   11.807(2)
_cell_length_c                   20.471(3)
_cell_measurement_reflns_used    4660
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.63
_cell_volume                     2936.2(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.669
_diffrn_measured_fraction_theta_max 0.669
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10652
_diffrn_reflns_theta_full        23.34
_diffrn_reflns_theta_max         23.34
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.026(5)
_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   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0763
_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^)+(0.1233P)^2^+5.4783P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2190
_refine_ls_wR_factor_ref         0.2273
_reflns_number_gt                2548
_reflns_number_total             2860
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102639a_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2936.3(10)
_cod_database_code               4102484