Multifunctional PNN-NiII pincer catalyst for C–C and C–N bond formation via alkylation, cross-coupling, and hydroamination reactions
Sabharwal, Gazal; Dwivedi, Khilesh C.; Balakrishna, Maravanji S.; Catalysis Science & Technology 15 (2025) 5275–5284; doi:10.1039/D5CY00718F

data_1575235
_publ_section_title
;
 Multifunctional PNN-NiII pincer catalyst for C--C and C--N bond formation
 via alkylation, cross-coupling, and hydroamination reactions
;
_journal_issue                   18
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5275
_journal_page_last               5284
_journal_paper_doi               10.1039/D5CY00718F
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C25 H21 N2 O2 P'
_chemical_formula_sum            'C25 H21 N2 O2 P'
_chemical_formula_weight         412.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-09-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-05-30 deposited with the CCDC.	2025-07-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2533(2)
_cell_length_b                   14.3859(3)
_cell_length_c                   15.5532(4)
_cell_measurement_reflns_used    5747
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      25.5910
_cell_measurement_theta_min      2.5510
_cell_volume                     2070.40(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    187.79 323.79   0.50    4.00  15.81  -9.84 -59.25    --   272
  2  \f     -6.01 129.99   0.50    4.00   6.61  -9.84 -31.50    --   272
  3  \w   -100.81  15.69   0.50    4.00    --   -9.84 -59.25  20.08  233
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33517
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.713
_diffrn_reflns_theta_min         1.928
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2023 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         7056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0332P)^2^+0.4136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                5653
_reflns_number_total             7056
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cy00718f2.cif
_cod_data_source_block           OPN(H)N_6
_cod_depositor_comments
'Adding full bibliography for 1575233--1575235.cif.'
_cod_database_code               1575235
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C12(H12), C21(H21), C25(H25), C4(H4), C19(H19), C11(H11), C24(H24),
 C10(H10), C16(H16), C18(H18), C9(H9), C23(H23), C22(H22), C2(H2), C17(H17),
 C1(H1), C3(H3)
;
_shelx_res_checksum              11439
_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
;