Understanding Ni(II)-Mediated C(sp<sup>3</sup>)-H Activation: Tertiary Ureas as Model Substrates.
Beattie, D. Dawson; Grunwald, Anna C.; Perse, Thibaut; Schafer, Laurel L.; Love, Jennifer A.; Journal of the American Chemical Society 140 (2018) 12602–12610; doi:10.1021/jacs.8b07708

data_4132975
_publ_section_title
;
 Understanding Ni(II)-Mediated C(sp<sup>3</sup>)-H Activation: Tertiary
 Ureas as Model Substrates.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12602
_journal_page_last               12610
_journal_paper_doi               10.1021/jacs.8b07708
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C32 H66 Ni2 O8 P2'
_chemical_formula_sum            'C32 H66 Ni2 O8 P2'
_chemical_formula_weight         758.20
_chemical_name_systematic        '[(PEt3)Ni(mu2-O,O-tBuCOO)2]2'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.0940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9146(6)
_cell_length_b                   17.8444(12)
_cell_length_c                   12.4027(8)
_cell_measurement_reflns_used    398
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.433
_cell_measurement_theta_min      5.139
_cell_volume                     2073.6(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.492
_diffrn_reflns_theta_min         2.079
_exptl_absorpt_coefficient_mu    1.025
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0355 before and 0.0323 after correction. The Ratio of minimum to maximum transmission is 0.9390. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         6312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0330P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5098
_reflns_number_total             6312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07708_si_004.cif
_cod_data_source_block           mo_jl294_01m
_cod_database_code               4132975
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.821
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15B)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
 Sof(C8)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C10)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C11)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(2)
 Sof(C8B)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=Sof(C10B)=Sof(H10A)=Sof(H10B)=
 Sof(H10C)=Sof(C11B)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B)
3.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C9B(H9BA,H9BB,H9BC),
 C10B(H10A,H10B,H10C), C11B(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C9(H9A,H9B,H9C), C10(H10D,H10E,H10F), C11(H11D,
 H11E,H11F), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F), C16B(H16D,H16E,H16F)
;
_shelx_res_checksum              92419
_shelx_hkl_checksum              64257
_olex2_submission_special_instructions 'No special instructions were received'