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_4132976
_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         'C23 H34 N3 Ni O P, 0.5(C7 H8)'
_chemical_formula_sum            'C26.5 H38 N3 Ni O P'
_chemical_formula_weight         504.28
_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                 99.6020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7609(5)
_cell_length_b                   16.9421(7)
_cell_length_c                   28.0175(13)
_cell_measurement_reflns_used    8912
_cell_measurement_temperature    90
_cell_measurement_theta_max      29.067
_cell_measurement_theta_min      2.276
_cell_volume                     5036.4(4)
_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_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            91204
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.214
_diffrn_reflns_theta_min         1.410
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0552 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.9331. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             2152
_exptl_crystal_recrystallization_method 'tol layered with HMDSO'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         13633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0145P)^2^+13.0817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10606
_reflns_number_total             13633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07708_si_003.cif
_cod_data_source_block           mo_jl283_0m
_cod_original_formula_sum        'C26.50 H38 N3 Ni O P'
_cod_database_code               4132976
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C3B(H3B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C18(H18A,H18B), C20(H20A,H20B), C23(H23A,H23B), C1B(H1BA,H1BB), C4B(H4BA,H4BB),
  C5B(H5BA,H5BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB), C18B(H18C,
 H18D), C20B(H20C,H20D), C22B(H22D,H22E)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C10B(H10B),
 C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B), C16B(H16B), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C19B(H19D,H19E,
 H19F), C21B(H21D,H21E,H21F), C23B(H23C,H23D,H23E), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              58198
_shelx_hkl_checksum              16760
_olex2_submission_original_sample_id jl283
_olex2_submission_special_instructions 'No special instructions were received'