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_4026580
_publ_contact_author_address
; 
 Department of Chemistry, 
 Temple Hall 456, 
 Missouri State University, 
 Springfield, MO 65897, USA. 
;
_publ_contact_author_email       NNGerasimchuk@missouristate.edu
_publ_contact_author_fax         '1 417 836 5507'
_publ_contact_author_name        'Prof. Nikolay Gerasimchuk'
_publ_contact_author_phone       '1 417 836 5165'
_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 S
_chemical_formula_moiety         'C49 H48 Cl Cu N2, C4 H10 O'
_chemical_formula_sum            'C53 H58 Cl Cu N2 O'
_chemical_formula_weight         838.00
_chemical_name_systematic
; 
 Chiral Cu(I)-Cl-pyrazolyl-complex 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 115.0970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.7516(11)
_cell_length_b                   11.2673(8)
_cell_length_c                   14.1985(10)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.15
_cell_measurement_theta_min      2.54
_cell_volume                     2282.0(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       'omega and phi 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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22695
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.9428
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5257
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                4388
_reflns_number_total             5257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2012434_si_004.cif
_cod_data_source_block           bg-2_crystal-1
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4026580