Sequential Michael addition, cross-coupling and [3 + 2] cycloaddition reactions within the coordination sphere of chiral Ni(ii) Schiff base complexes derived from dehydroamino acids: pathways to the asymmetric synthesis of structurally diverse O-substituted serine and threonine analogs
Khachatryan, Emma A.; Sahakyan, Lusine Yu.; Tovmasyan, Anna S.; Melikyan, Gagik S.; Panosyan, Henrik A.; Mkrtchyan, Anna F.; Shibata, Norio; Malkov, Andrei V.; Saghyan, Ashot S.; RSC Advances 15 (2025) 10558–10564; doi:10.1039/D5RA00910C

data_7250228
_publ_section_title
;
 Sequential Michael addition, cross-coupling and [3 + 2] cycloaddition
 reactions within the coordination sphere of chiral Ni(ii) Schiff base
 complexes derived from dehydroamino acids: pathways to the asymmetric
 synthesis of structurally diverse O-substituted serine and threonine
 analogs
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              10558
_journal_page_last               10564
_journal_paper_doi               10.1039/D5RA00910C
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C32 H31 N3 Ni O4, C2 H6 O, H2 O'
_chemical_formula_sum            'C34 H39 N3 Ni O6'
_chemical_formula_weight         644.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.5650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.41050(10)
_cell_length_b                   11.87270(10)
_cell_length_c                   14.0699(2)
_cell_measurement_reflns_used    42074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0690
_cell_measurement_theta_min      2.7240
_cell_volume                     1564.59(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'ORTEP-3 (Ferrugia, 2012)'
_computing_publication_material  'enCIFer version 1.7 (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46938
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.067
_diffrn_reflns_theta_min         2.174
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 3669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         8379
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0226
_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^)+(0.0345P)^2^+0.3559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0581
_refine_ls_wR_factor_ref         0.0583
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                8256
_reflns_number_total             8379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra00910c2.cif
_cod_data_source_block           LYS-026_100k_auto
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7250228
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.766
_shelx_estimated_absorpt_t_max   0.867
_shelx_res_checksum              36819