One-Pot, Single-Step, and Gram-Scale Synthesis of Mononuclear [(η6-arene)Ni(N-heterocyclic carbene)] Complexes: Useful Precursors of the Ni0‒NHC Unit
Hoshimoto, Yoichi; Hayashi, Yukari; Suzuki, Haruka; Ohashi, Masato; Ogoshi, Sensuke; Organometallics 33 (2014) 1276–; doi:10.1021/om500088p

data_4082690
_publ_section_title
;
 One-Pot, Single-Step, and Gram-Scale Synthesis of Mononuclear
 [(\h6-arene)Ni(N-heterocyclic carbene)] Complexes: Useful Precursors of
 the Ni0--NHC Unit
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              1276
_journal_paper_doi               10.1021/om500088p
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C75 H56 N2 Ni, 0.5(C6 H6)'
_chemical_formula_sum            'C78 H59 N2 Ni'
_chemical_formula_weight         1082.98
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0859(15)
_cell_length_b                   24.0588(16)
_cell_length_c                   28.841(2)
_cell_measurement_reflns_used    24376
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.425
_cell_measurement_theta_min      3.00
_cell_volume                     13937.2(17)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013) and modified'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'PATTY (Bueskens, et al., 1994)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.3949
_diffrn_reflns_av_unetI/netI     0.2552
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            87262
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.078
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.032
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4552
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_platon_squeeze_details
;
The unit cell contains sixteen pentane molecules which have been treated
as a diffuse contribution to the overall scattering without specific
atom positions by SQUEEZE/PLATON. 

TITL shelxl    P b c a      R = 0.16
CELL   20.0859   24.0588   28.8410     90.00     90.00     90.00
SPGR Pbca
C101 0.389 0.610 0.608 !       4.52 eA-3
C102 0.775 0.899 0.409 !       4.44 eA-3
C103 0.237 0.460 0.077 !       3.86 eA-3
C104 0.341 0.618 0.581 !       3.63 eA-3
C105 0.059 0.833 0.585 !       3.63 eA-3
C106 0.304 0.017 0.571 !       3.42 eA-3
C107 0.774 0.337 0.891 !       3.22 eA-3
C108 0.548 0.140 0.903 !       3.10 eA-3
C109 0.124 0.858 0.571 !       3.07 eA-3
C110 0.494 0.306 0.523 !       3.05 eA-3
C111 0.549 0.851 0.951 !       2.98 eA-3
C112 0.011 0.313 0.976 !       2.94 eA-3
C113 0.051 0.853 0.529 !       2.88 eA-3
C114 0.068 0.631 0.057 !       2.71 eA-3
C115 0.814 0.162 0.407 !       2.66 eA-3
C116 0.801 0.136 0.407 !       2.64 eA-3
C117 0.841 0.120 0.385 !       2.60 eA-3
C118 0.730 0.829 0.898 !       2.59 eA-3
C119 0.919 0.150 0.414 !       2.54 eA-3
C120 0.807 0.994 0.391 !       2.48 eA-3
C121 0.553 0.830 0.906 !       2.48 eA-3
C122 0.245 0.008 0.570 !       2.46 eA-3
C123 0.181 0.882 0.587 !       2.46 eA-3
C124 0.978 0.163 0.469 !       2.43 eA-3
C125 0.724 0.845 0.898 !       2.38 eA-3
C126 0.086 0.649 0.108 !       2.38 eA-3
C127 0.954 0.639 0.912 !       2.36 eA-3
C128 0.932 0.337 0.970 !       2.36 eA-3
C129 0.137 0.624 0.102 !       2.34 eA-3
C130 0.164 0.423 0.110 !       2.28 eA-3
C131 0.915 0.140 0.469 !       2.26 eA-3
C132 0.829 0.976 0.398 !       2.26 eA-3
C133 0.621 0.424 0.366 !       2.25 eA-3
C134 0.994 0.322 0.946 !       2.18 eA-3
C135 0.985 0.670 0.040 !       2.18 eA-3
C136 0.734 0.993 0.923 !       2.16 eA-3
C137 0.249 0.916 0.064 !       2.11 eA-3
C138 0.948 0.824 0.461 !       2.09 eA-3
C139 0.633 0.607 0.439 !       2.08 eA-3
C140 0.576 0.179 0.970 !       2.05 eA-3
C141 0.230 0.576 0.570 !       2.04 eA-3
C142 0.583 0.842 0.940 !       2.04 eA-3
C143 0.162 0.892 0.554 !       2.02 eA-3
C144 0.613 0.657 0.437 !       2.00 eA-3
C145 0.326 0.157 0.062 !       1.98 eA-3
C146 0.796 0.196 0.375 !       1.96 eA-3
C147 0.800 0.945 0.399 !       1.92 eA-3
C148 0.188 0.445 0.078 !       1.87 eA-3
C149 0.924 0.320 0.906 !       1.87 eA-3
C150 0.372 0.390 0.586 !       1.86 eA-3
C151 0.108 0.861 0.538 !       1.80 eA-3
Q152 0.386 0.304 0.524 !       1.76 eA-3
C153 0.223 0.101 0.618 !       1.75 eA-3
C154 0.370 0.571 0.600 !       1.74 eA-3
C155 0.703 0.913 0.392 !       1.71 eA-3
Q156 0.534 0.937 0.095 !       1.71 eA-3
C157 0.095 0.901 0.578 !       1.69 eA-3
C158 0.190 0.623 0.109 !       1.69 eA-3
C159 0.839 0.635 0.960 !       1.67 eA-3
C160 0.155 0.321 0.069 !       1.65 eA-3
C161 1.007 0.715 0.025 !       1.65 eA-3
Q162 0.647 0.460 0.930 !       1.64 eA-3
C163 0.552 0.155 0.963 !       1.63 eA-3
C164 0.200 0.022 0.595 !       1.63 eA-3
C165 0.184 0.071 0.600 !       1.63 eA-3
C166 0.744 0.189 0.358 !       1.62 eA-3
C167 0.938 0.365 0.000 !       1.61 eA-3
C168 0.981 0.812 0.502 !       1.61 eA-3
C169 0.942 0.844 0.429 !       1.59 eA-3
Q170 0.776 0.366 0.452 !       1.57 eA-3
C171 0.015 0.298 0.937 !       1.56 eA-3
C172 0.460 0.311 0.562 !       1.56 eA-3
Q173 0.598 0.999 0.844 !       1.56 eA-3
C174 0.233 0.331 0.594 !       1.54 eA-3
C175 0.895 0.631 0.953 !       1.54 eA-3
C176 0.756 0.494 0.914 !       1.53 eA-3
C177 0.934 0.819 0.429 !       1.53 eA-3
C178 0.898 0.110 0.398 !       1.51 eA-3
C179 0.035 0.189 0.515 !       1.50 eA-3
C180 0.192 0.039 0.055 !       1.48 eA-3
C181 0.805 0.157 0.367 !       1.47 eA-3
C182 0.121 0.847 0.523 !       1.47 eA-3
C183 0.341 0.779 0.054 !       1.47 eA-3
Q184 0.238 0.842 0.680 !       1.46 eA-3
C185 0.777 0.470 0.448 !       1.46 eA-3
Q186 0.063 0.594 0.921 !       1.45 eA-3
C187 0.665 0.867 0.961 !       1.45 eA-3
C188 0.993 0.148 0.516 !       1.44 eA-3
C189 0.987 0.287 0.009 !       1.42 eA-3
C190 0.859 0.123 0.463 !       1.42 eA-3
C191 0.569 0.801 0.945 !       1.41 eA-3
C192 0.220 0.807 0.584 !       1.41 eA-3
C193 0.615 0.452 0.392 !       1.41 eA-3
Q194 0.621 0.797 0.946 !       1.41 eA-3
Q195 0.385 0.501 0.570 !       1.40 eA-3
C196 0.737 0.330 0.867 !       1.39 eA-3
Q197 0.587 0.547 0.351 !       1.38 eA-3
C198 0.896 0.829 0.460 !       1.37 eA-3
C199 0.713 0.892 0.461 !       1.37 eA-3
;
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         12139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.2306
_refine_ls_R_factor_gt           0.0967
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1010P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4414
_reflns_number_total             12139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500088p_si_002.cif
_cod_data_source_block           BNI*
_cod_original_cell_volume        13937.1(17)
_cod_database_code               4082690
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2013-4
_shelx_res_checksum              35632
_shelx_fab_checksum              23195