Nickel(II) - NɅNɅO Pincer Type Complexes Catalyzed N-alkylation of Amines with Alcohols via Hydrogen Auto Transfer Reaction.
Balamurugan, Gunasekaran; Ramesh, Rengan; Malecki, Jan Grzegorz; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00530

data_4038395
_publ_section_title
;
 Nickel(II) - N&#x0245;N&#x0245;O Pincer Type Complexes Catalyzed
 N-alkylation of Amines with Alcohols via Hydrogen Auto Transfer Reaction.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00530
_journal_year                    2020
_chemical_formula_moiety         'C32 H28 N3 Ni O2 P'
_chemical_formula_sum            'C32 H28 N3 Ni O2 P'
_chemical_formula_weight         576.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2019-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.831(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6894(6)
_cell_length_b                   12.8738(4)
_cell_length_c                   25.5940(8)
_cell_measurement_reflns_used    7544
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.7930
_cell_measurement_theta_min      3.9880
_cell_volume                     5924.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.56a (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -20.00  38.00   1.00   13.72    --   10.22  77.00  90.00   58
  2  \w     19.00  51.00   1.00   13.72    --   10.22 -99.00-150.00   32
  3  \w    -94.00 -14.00   1.00   13.72    --  -11.15   0.00-120.00   80
  4  \w     39.00  65.00   1.00   13.72    --  -11.15   0.00-120.00   26
  5  \w    -39.00 -10.00   1.00   13.72    --  -11.15  57.00 -60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0256147000
_diffrn_orient_matrix_UB_12      -0.0407544000
_diffrn_orient_matrix_UB_13      -0.0100426000
_diffrn_orient_matrix_UB_21      -0.0245672000
_diffrn_orient_matrix_UB_22      0.0359008000
_diffrn_orient_matrix_UB_23      -0.0168887000
_diffrn_orient_matrix_UB_31      0.0172063000
_diffrn_orient_matrix_UB_32      -0.0093833000
_diffrn_orient_matrix_UB_33      -0.0210556000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17293
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.337
_diffrn_reflns_theta_min         3.387
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.56a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       plate
_exptl_crystal_F_000             2400
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         7025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0436P)^2^+4.0968P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5289
_reflns_number_total             7025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00530_si_003.cif
_cod_data_source_block           nipk2
_cod_original_cell_volume        5924.4(4)
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4038395
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H28 N3 O1 P1 Ni1'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.802