Connecting Neutral and Cationic Pathways in Nickel-Catalyzed Insertion of Benzaldehyde into a C‒H Bond of Acetonitrile
Smith, Jacob B.; Miller, Alexander J. M.; Organometallics 34 (2015) 4669–; doi:10.1021/acs.organomet.5b00405

data_4086036
_publ_section_title
;
 Connecting Neutral and Cationic Pathways in Nickel-Catalyzed Insertion of
 Benzaldehyde into a C--H Bond of Acetonitrile
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4669
_journal_paper_doi               10.1021/acs.organomet.5b00405
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C23 H39 Br N Ni O5 P'
_chemical_formula_sum            'C23 H39 Br N Ni O5 P'
_chemical_formula_weight         579.14
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n'
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.9741(3)
_cell_length_b                   24.9741(3)
_cell_length_c                   8.09970(10)
_cell_measurement_reflns_used    3209
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.07
_cell_measurement_theta_min      3.54
_cell_volume                     5051.83(11)
_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, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            30343
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.144
_diffrn_reflns_theta_min         2.502
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.836
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.8284.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       needle
_exptl_crystal_F_000             2416
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.095
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0298P)^2^+2.6312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3834
_reflns_number_total             4785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om5b00405_si_002.cif
_cod_data_source_block           jbs014
_cod_depositor_comments          'Adding full bibliography for 4086036.cif.'
_cod_original_cell_volume        5051.83(14)
_cod_database_code               4086036
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.493
_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:
 C21(H21), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C11(H11A,H11B), C8(H8A,H8B), C16(H16A,H16B),
 C15(H15A,H15B), C17(H17A,H17B), C10(H10A,H10B), C9(H9A,H9B), C12(H12A,H12B),
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C22(H22A,H22B,
 H22C)
;
_shelx_res_checksum              49205
_shelx_hkl_checksum              8610
_olex2_submission_special_instructions 'No special instructions were received'