Bimetallic Nickel Complexes for Aniline C–H Alkylations
Ghorai, Debasish; Finger, Lars H.; Zanoni, Giuseppe; Ackermann, Lutz; ACS Catalysis 8 (2018) 11657–; doi:10.1021/acscatal.8b03770

data_4515797
_publ_section_title
;
 Bimetallic Nickel Complexes for Aniline C--H Alkylations
;
_journal_issue                   12
_journal_name_full               'ACS Catalysis'
_journal_page_first              11657
_journal_paper_doi               10.1021/acscatal.8b03770
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C40 H28 F4 N12 Ni2'
_chemical_formula_sum            'C40 H28 F4 N12 Ni2'
_chemical_formula_weight         870.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5253(4)
_cell_length_b                   16.5175(7)
_cell_length_c                   22.4483(10)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    99.97
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.63
_cell_volume                     3531.9(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            50612
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.530
_diffrn_reflns_theta_min         2.630
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  0.2671
_exptl_absorpt_correction_T_min  0.2076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1250 before and 0.0738 after correction. The Ratio of minimum to maximum transmission is 0.7772. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and pentane  by solvent layering'
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.108
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.353
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5891
_refine_ls_number_restraints     141
_refine_ls_restrained_S_all      1.340
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0678
_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^)+18.2712P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5607
_reflns_number_total             5891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03770_si_003.cif
_cod_data_source_block           0411_cg_0m
_cod_database_code               4515797
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.593
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 F1, C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, C5, C7, C11, C12, C13, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3, C20, C19, C24, F4, C23, C22, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F2)=Sof(H7B)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=
 Sof(C14)=1-FVAR(1)
 Sof(F1)=Sof(C6)=Sof(H7A)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=
 FVAR(1)
 Sof(F4)=Sof(H20)=1-FVAR(2)
 Sof(F3)=Sof(H24)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7A), C7(H7B), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24)
;
_shelx_res_checksum              98755
_shelx_hkl_checksum              75815
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'