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_4026578
_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_formula_moiety         'C25 H37 N2 Si2, Cl'
_chemical_formula_sum            'C25 H37 Cl N2 Si2'
_chemical_formula_weight         457.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.1-2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4419(5)
_cell_length_b                   13.7473(8)
_cell_length_c                   24.4406(14)
_cell_measurement_reflns_used    110
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      18.8177
_cell_measurement_theta_min      3.0712
_cell_volume                     2836.4(3)
_computing_cell_refinement       'APEX2 v2010.1-2 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27620
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G.M. (2008) SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.'
_exptl_crystal_density_diffrn    1.071
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.413
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0354
_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^)+(0.0656P)^2^+0.2573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                4576
_reflns_number_total             5005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2012434_si_002.cif
_cod_data_source_block           I
_cod_database_code               4026578