Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors and Metal Carbenoids
Abigail Albright; Daniel Eddings; Regina Black; Christopher J. Welch; Nikolay N. Gerasimchuk; Robert E. Gawley; Journal of Organic Chemistry 76 (2011) 7341–7351; doi:10.1021/jo2012434

data_4026577
_publ_section_title
;
 Design and Synthesis of C2-Symmetric N-Heterocyclic Carbene Precursors
 and Metal Carbenoids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7341
_journal_page_last               7351
_journal_paper_doi               10.1021/jo2012434
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C43 H39 N2, F6 P, C H Cl3'
_chemical_formula_sum            'C44 H40 Cl3 F6 N2 P'
_chemical_formula_weight         848.10
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.5024(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7329(1)
_cell_length_b                   21.7097(3)
_cell_length_c                   9.7718(1)
_cell_measurement_reflns_used    5275
_cell_measurement_temperature    123
_cell_measurement_theta_max      66.4417
_cell_measurement_theta_min      4.0635
_cell_volume                     2058.39(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
;
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.5431
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Oxford Diffraction Gemini Ultra'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8542
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.65
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_min         4.07
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       platelike
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         5267
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0495P)^2^+1.4936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                4741
_reflns_number_total             5267
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo2012434_si_001.cif
_cod_data_source_block           h144
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026577