Nickel-catalyzed hydroimination of alkynes.
Manan, Rajith S.; Kilaru, Praveen; Zhao, Pinjing; Journal of the American Chemical Society 137 (2015) 6136–6139; doi:10.1021/jacs.5b02272

data_4123652
_publ_section_title
;
 Nickel-catalyzed hydroimination of alkynes.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6136
_journal_page_last               6139
_journal_paper_doi               10.1021/jacs.5b02272
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C53 H58 N4 Ni'
_chemical_formula_sum            'C53 H58 N4 Ni'
_chemical_formula_weight         809.74
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.174(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.539(3)
_cell_length_b                   18.204(4)
_cell_length_c                   19.354(4)
_cell_measurement_reflns_used    9189
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.616
_cell_measurement_theta_min      2.203
_cell_volume                     4414.6(17)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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  0.0716
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            49184
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.838
_diffrn_reflns_theta_min         1.536
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0855 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8143.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark black'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         8462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0533P)^2^+1.4886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6393
_reflns_number_total             8462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b02272_si_005.cif
_cod_data_source_block           mo_rxm27_0m
_cod_depositor_comments
'Adding full bibliography for 4123566--4123653.cif.'
_cod_original_cell_volume        4414.9(16)
_cod_database_code               4123652
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.901
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22),
 C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39), C40(H40), C41(H41),
  C42(H42), C43(H43), C47(H47), C48(H48), C49(H49), C50(H50), C51(H51),
 C53(H53), C54(H54), C55(H55), C56(H56), C57(H57)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,
 H29B,H29C)
;
_shelx_res_checksum              88311
_shelx_hkl_checksum              18772
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'