Green Synthesis of α-Aminophosphonates: From Hydrogen-Bonded Janus Dimers to Pharmaceutical Potential
Kholany, Rawda; Mardini, Alaa A.; Shakirova, Ksenia; Islamov, Daut; Gerasimov, Alexander; Klimovitskii, Alexander; Vavilova, Alena A.; Mostovaya, Olga; Gazizova, Asiya; Stoikov, Ivan; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01712B

data_7160905
_publ_section_title
;
 Green Synthesis of \a-Aminophosphonates: From Hydrogen-Bonded Janus
 Dimers to Pharmaceutical Potential
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01712B
_journal_year                    2025
_chemical_formula_moiety         'C13 H21 N2 O4 P'
_chemical_formula_sum            'C13 H21 N2 O4 P'
_chemical_formula_weight         300.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2025-10-20 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.24880(10)
_cell_length_b                   14.78870(10)
_cell_length_c                   11.20740(10)
_cell_measurement_reflns_used    13461
_cell_measurement_temperature    304.06(10)
_cell_measurement_theta_max      75.6210
_cell_measurement_theta_min      2.9290
_cell_volume                     1524.84(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.80a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      304.06(10)
_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 0.986
_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     25.00 107.00   0.50    0.05    --   46.31  77.00 -60.00  164
  2  \w     92.00 162.00   0.50    0.16    --  103.80  77.00 -60.00  140
  3  \w    142.00 167.00   0.50    0.16    --  103.80  45.00 -30.00   50
  4  \w    141.00 178.00   0.50    0.16    --  103.80  15.00-120.00   74
  5  \w     90.00 122.00   0.50    0.16    --  103.80  15.00-120.00   64
  6  \w     92.00 118.00   0.50    0.16    --  103.80  45.00 -30.00   52
  7  \w     -2.00  23.00   0.50    0.05    --   46.31 -19.00 120.00   50
  8  \w     31.00  75.00   0.50    0.16    --  103.80 -77.00 120.00   88
  9  \w     34.00 100.00   0.50    0.16    --  103.80-125.00  60.00  132
 10  \w     70.00  95.00   0.50    0.16    --  103.80-120.00 147.00   50
 11  \w     11.00  61.00   0.50    0.05    --   46.31-120.00 147.00  100
 12  \w     32.00 130.00   0.50    0.16    --  103.80-154.00 -10.00  196
 13  \w     83.00 111.00   0.50    0.05    --   46.31-154.00 -10.00   56
 14  \w     32.00  71.00   0.50    0.16    --  103.80 -61.00 -60.00   78
 15  \w     60.00 116.00   0.50    0.05    --   46.31 154.00  29.00  112
 16  \w     74.00  99.00   0.50    0.05    --   46.31 125.00 -30.00   50
 17  \w    100.00 133.00   0.50    0.16    --  103.80 120.00-128.00   66
 18  \w     90.00 117.00   0.50    0.05    --   46.31 125.00   0.00   54
 19  \w     74.00 119.00   0.50    0.05    --   46.31 125.00 120.00   90
 20  \w    -94.00 -69.00   0.50    0.05    --  -47.56 154.00  29.00   50
 21  \w   -131.00 -81.00   0.50    0.16    -- -105.05 154.00  29.00  100
 22  \w    -75.00 -36.00   0.50    0.16    -- -105.05 154.00  29.00   78
 23  \w   -102.00 -34.00   0.50    0.16    -- -105.05 125.00 -60.00  136
 24  \w   -127.00-102.00   0.50    0.16    -- -105.05 146.00 -68.18   50
 25  \w    -96.00 -71.00   0.50    0.16    -- -105.05 125.00-180.00   50
 26  \w   -112.00 -34.00   0.50    0.16    -- -105.05 125.00-150.00  156
 27  \w    -67.00 -37.00   0.50    0.16    -- -105.05 125.00-180.00   60
 28  \w    -88.00 -35.00   0.50    0.05    --  -47.56 120.00-128.00  106
 29  \w    -95.00 -70.00   0.50    0.16    -- -105.05 120.00-128.00   50
 30  \w    -86.00 -61.00   0.50    0.16    -- -105.05 146.00 -68.18   50
 31  \w   -112.00 -36.00   0.50    0.16    -- -105.05 125.00   0.00  152
 32  \w   -112.00 -84.00   0.50    0.16    -- -105.05 125.00 150.00   56
 33  \w    -82.00 -40.00   0.50    0.16    -- -105.05  77.00  90.00   84
 34  \w    -26.00  28.00   0.50    0.05    --  -47.56  19.00  60.00  108
 35  \w    -11.00  24.00   0.50    0.05    --  -47.56  19.00-180.00   70
 36  \w    -71.00 -33.00   0.50    0.16    -- -105.05  61.00-180.00   76
 37  \w    -67.00 -33.00   0.50    0.16    -- -105.05  61.00-150.00   68
 38  \w    -71.00 -32.00   0.50    0.16    -- -105.05  61.00-120.00   78
 39  \w   -177.00 -91.00   0.50    0.16    -- -105.05 -61.00-180.00  172
 40  \w   -177.00-101.00   0.50    0.16    -- -105.05 -45.00  60.00  152
 41  \w   -124.00 -98.00   0.50    0.16    -- -105.05 -45.00 150.00   52
 42  \w   -177.00-134.00   0.50    0.16    -- -105.05 -45.00 150.00   86
 43  \w   -151.00-126.00   0.50    0.16    -- -105.05-120.00 147.00   50
 44  \w   -118.00 -90.00   0.50    0.05    --  -47.56-154.00 -10.00   56
 45  \w    -87.00 -54.00   0.50    0.05    --  -47.56-154.00 -10.00   66
 46  \w   -132.00-107.00   0.50    0.16    -- -105.05-154.00 -10.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0340832000
_diffrn_orient_matrix_UB_12      -0.1019655000
_diffrn_orient_matrix_UB_13      -0.0008230000
_diffrn_orient_matrix_UB_21      -0.1218962000
_diffrn_orient_matrix_UB_22      -0.0176634000
_diffrn_orient_matrix_UB_23      0.0810172000
_diffrn_orient_matrix_UB_31      -0.1096376000
_diffrn_orient_matrix_UB_32      -0.0120554000
_diffrn_orient_matrix_UB_33      -0.1119176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20745
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.036
_diffrn_reflns_theta_min         4.968
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.308
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0662P)^2^+0.4254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2919
_reflns_number_total             3142
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01712b2.cif
_cod_data_source_block           stoi869_corr
_cod_database_code               7160905
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C13H21N2O4P
_shelx_estimated_absorpt_t_max   0.712
_shelx_estimated_absorpt_t_min   0.558
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C10(H10), C13(H13)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C5(H5A,H5B,H5C), C11(H11A,H11B,H11C),
 C3(H3A,H3B,H3C)
;
_shelx_res_checksum              78386
_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 1.610
_oxdiff_exptl_absorpt_empirical_full_min 0.652