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_7064234
_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         'Cl, C18 H21 N O3 P, H2 O'
_chemical_formula_sum            'C18 H23 Cl N O4 P'
_chemical_formula_weight         383.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-04-04 deposited with the CCDC.	2026-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.174(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.337(4)
_cell_length_b                   16.965(10)
_cell_length_c                   9.393(5)
_cell_measurement_reflns_used    2518
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.40
_cell_volume                     979.1(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0695
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8828
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.989
_diffrn_reflns_theta_min         2.401
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1100 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.7385.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
;
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0889P)^2^+2.2789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2041
_refine_ls_wR_factor_ref         0.2140
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.748
_reflns_number_gt                3009
_reflns_number_total             3706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj04753f2.cif
_cod_data_source_block           dp372_0m
_cod_depositor_comments
'Adding full bibliography for 7064233--7064234.cif.'
_cod_original_cell_volume        979.0(10)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7064234
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.888
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H2-O4
 1.711 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C2) = Uanis(C3)
4.a Free rotating group:
 O4(H4A,H4B)
4.b Ternary CH refined with riding coordinates:
 C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
4.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18)
4.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              68738
_olex2_submission_special_instructions 'No special instructions were received'