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_4102485
_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            'C39 H45 N2 P'
_chemical_formula_weight         572.74
_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                 107.355(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.5148(17)
_cell_length_b                   10.5459(12)
_cell_length_c                   20.489(2)
_cell_measurement_reflns_used    1091
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.57
_cell_measurement_theta_min      3.23
_cell_volume                     3406.0(6)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47581
_diffrn_reflns_theta_full        30.17
_diffrn_reflns_theta_max         30.17
_diffrn_reflns_theta_min         1.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9019
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.97
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         10025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0486P)^2^+1.0760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                7398
_reflns_number_total             10025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102639a_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        3405.9(6)
_cod_database_code               4102485