Acceleration of the Arbuzov-type reaction via double activation of imine and H-phosphonate
Sidlyaruk, Nikita; Smolobochkin, Andrey; Gazizov, Almir; Rizbayeva, Tanzilya; Gerasimova, Daria; Garifzyanov, Airat; Shirokov, Valeriy; Burilov, Alexander; Pudovik, Michail; New Journal of Chemistry 50 (2026) 3615–3627; doi:10.1039/D5NJ04753F

data_7064233
_publ_section_title
;
 Acceleration of the Arbuzov-type reaction via double activation of imine
 and H-phosphonate
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3615
_journal_page_last               3627
_journal_paper_doi               10.1039/D5NJ04753F
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C17 H18 Br N O2 P, Cl, 0.5(H2 O)'
_chemical_formula_sum            'C17 H19 Br Cl N O2.5 P'
_chemical_formula_weight         423.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-04-02 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                93.138(2)
_cell_angle_beta                 100.567(2)
_cell_angle_gamma                93.351(2)
_cell_formula_units_Z            4
_cell_length_a                   6.6018(4)
_cell_length_b                   16.2369(9)
_cell_length_c                   16.8101(9)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.47
_cell_volume                     1764.40(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            72687
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         2.471
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1417 before and 0.0707 after correction.
The Ratio of minimum to maximum transmission is 0.8508.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       prism
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         7719
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0343
_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^)+(0.0313P)^2^+1.8211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6497
_reflns_number_total             7719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj04753f2.cif
_cod_data_source_block           dp370_0m
_cod_depositor_comments
'Adding full bibliography for 7064233--7064234.cif.'
_cod_original_formula_sum        'C17 H19 Br Cl N O2.50 P'
_cod_database_code               7064233
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.824
_shelx_estimated_absorpt_t_min   0.366
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O2A-H2A = O2B-H2B = O3-H3A = O3-H3B
 0.84 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C5A(H5A), C5B(H5B)
3.b Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C3A(H3AA,H3AB), C2B(H2BA,H2BB), C3B(H3BA,H3BB)
3.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C14A(H14A),
 C15A(H15A), C17A(H17A), C18A(H18A), C7B(H7B), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B), C17B(H17B), C18B(H18B)
;
_shelx_res_checksum              42162
_olex2_submission_special_instructions 'No special instructions were received'