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_4038396
_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         'C31 H26 N3 Ni O P, C2 H6 O'
_chemical_formula_sum            'C33 H32 N3 Ni O2 P'
_chemical_formula_weight         592.29
_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   mixed
_audit_creation_date             2018-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.687(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.6292(11)
_cell_length_b                   12.8456(8)
_cell_length_c                   25.5273(14)
_cell_measurement_reflns_used    5398
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.6520
_cell_measurement_theta_min      3.9770
_cell_volume                     5851.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.851
_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    -79.00 -54.00   1.00  144.98    --    9.75-179.00  60.00   25
  2  \w    -84.00 -18.00   1.00  144.98    --  -11.93 -38.00 -90.00   66
  3  \w    -92.00  19.00   1.00  144.98    --  -11.93 -19.00 -30.00  111
;
_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      0.0057337000
_diffrn_orient_matrix_UB_12      0.0156958000
_diffrn_orient_matrix_UB_13      -0.0251327000
_diffrn_orient_matrix_UB_21      -0.0379777000
_diffrn_orient_matrix_UB_22      0.0158401000
_diffrn_orient_matrix_UB_23      -0.0096327000
_diffrn_orient_matrix_UB_31      0.0101150000
_diffrn_orient_matrix_UB_32      0.0505713000
_diffrn_orient_matrix_UB_33      0.0108097000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15386
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.476
_diffrn_reflns_theta_min         3.457
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       prism
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0623P)^2^+1.9156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5149
_reflns_number_total             6938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00530_si_002.cif
_cod_data_source_block           nipyp1
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4038396
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C31 H28 N3 Ni1 O1 P1'
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, All O(H) groups
2.a Riding coordinates:
 O2(H2A), C32(H32A,H32B,H32C), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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 1.928
_oxdiff_exptl_absorpt_empirical_full_min 0.799