Nickel(II) Benzimidazolin-2-ylidene Complexes with Thioether-Functionalized Side Chains as Catalysts for Suzuki‒Miyaura Cross-Coupling
Bernhammer, Jan C.; Huynh, Han Vinh; Organometallics 33 (2014) 5845–; doi:10.1021/om500484q

data_4084037
_publ_section_title
;
 Nickel(II) Benzimidazolin-2-ylidene Complexes with
 Thioether-Functionalized Side Chains as Catalysts for Suzuki--Miyaura
 Cross-Coupling
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5845
_journal_paper_doi               10.1021/om500484q
_journal_volume                  33
_journal_year                    2014
_chemical_formula_sum            'C38 H44 Br2 N4 Ni S2'
_chemical_formula_weight         839.42
_chemical_name_systematic
; 
 ? 
;
_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                 91.825(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.682(3)
_cell_length_b                   18.283(5)
_cell_length_c                   9.480(3)
_cell_measurement_reflns_used    866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.21
_cell_volume                     1850.5(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12661
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_correction_T_min  0.4232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.863
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0724
_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^)+(0.1474P)^2^+0.7715P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2390
_reflns_number_gt                2848
_reflns_number_total             4243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500484q_si_002.cif
_cod_data_source_block           d294a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1850.6(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4084037