Readily Accessible Unsymmetrical Unsaturated 2,6-Diisopropylphenyl N-Heterocyclic Carbene Ligands. Applications in Enantioselective Catalysis.
Tarrieu, Robert; Dumas, Adrien; Thongpaen, Jompol; Vives, Thomas; Roisnel, Thierry; Dorcet, Vincent; Crévisy, Christophe; Baslé, Olivier; Mauduit, Marc; The Journal of organic chemistry 82 (2017) 1880–1887; doi:10.1021/acs.joc.6b02888

data_4032169
_publ_section_title
;
 Readily Accessible Unsymmetrical Unsaturated 2,6-Diisopropylphenyl
 N-Heterocyclic Carbene Ligands. Applications in Enantioselective
 Catalysis.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1880
_journal_page_last               1887
_journal_paper_doi               10.1021/acs.joc.6b02888
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H30 Cl Cu N2'
_chemical_formula_sum            'C27 H30 Cl Cu N2'
_chemical_formula_weight         481.52
_chemical_name_systematic
;
 ?
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   15.1197(9)
_cell_length_b                   17.6938(11)
_cell_length_c                   28.1469(17)
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.44
_cell_measurement_theta_min      2.46
_cell_measurement_wavelength     0.71073
_cell_volume                     7530.0(8)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_av_unetI/netI     0.1744
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            40269
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.930
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
Flack x determined using 2584 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     853
_refine_ls_number_reflns         17121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1634
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0258P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                8723
_reflns_number_total             17121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02888_si_001.cif
_cod_data_source_block           RT424
_cod_depositor_comments
'Adding full bibliography for 4032167--4032170.cif.'
_cod_database_code               4032169
_shelx_res_checksum              55399