Sono- and mechanochemical dual syntheses of bio-relevant aryldiazenyl-substituted phosphine oxides/phosphonates via P(O)–H functionalisation
Mukherjee, Debojyoti; Karmakar, Indrajit; Brahmachari, Goutam; Green Chemistry 27 (2025) 2565–2577; doi:10.1039/D4GC05501B

data_7249880
_publ_section_title
;
 Sono- and mechanochemical dual syntheses of bio-relevant
 aryldiazenyl-substituted phosphine oxides/phosphonates via P(O)--H
 functionalisation
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              2565
_journal_page_last               2577
_journal_paper_doi               10.1039/D4GC05501B
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C20 H18 Br N2 O P'
_chemical_formula_sum            'C20 H18 Br N2 O P'
_chemical_formula_weight         413.24
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-21
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-10-24 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                86.124(8)
_cell_angle_beta                 89.703(8)
_cell_angle_gamma                73.686(8)
_cell_formula_units_Z            2
_cell_length_a                   6.9964(6)
_cell_length_b                   8.4138(8)
_cell_length_c                   17.0464(18)
_cell_measurement_reflns_used    1813
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.6980
_cell_measurement_theta_min      2.5920
_cell_volume                     960.75(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_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    -62.00 -36.00   1.00    1.00    --  -24.78  57.00-150.00   26
  2  \w    -62.00  16.00   1.00    1.00    --  -24.78  57.00 -30.00   78
  3  \w    -32.00  44.00   1.00    1.00    --  -24.78  57.00-150.00   76
  4  \w    -59.00  40.00   1.00    1.00    --  -24.78  77.00  60.00   99
  5  \w     21.00  51.00   1.00    1.00    --  -24.78  57.00 -30.00   30
  6  \w   -146.00 -55.00   1.00    1.00    --  -69.25 -50.00  60.00   91
  7  \w    -52.00 -26.00   1.00    1.00    --  -69.25 -50.00  60.00   26
  8  \w   -125.00 -39.00   1.00    1.00    --  -69.25 178.00  60.00   86
  9  \w   -138.00 -82.00   1.00    1.00    --  -69.25 -77.00-150.00   56
 10  \w    -81.00  -1.00   1.00    1.00    --  -69.25 111.00 -90.00   80
 11  \w    106.00 131.00   1.00    1.00    --   69.25 111.00 150.00   25
 12  \w     74.00 106.00   1.00    1.00    --   69.25 178.00   0.00   32
 13  \w    106.00 155.00   1.00    1.00    --   69.25  77.00-180.00   49
 14  \w     38.00 148.00   1.00    1.00    --   69.25  50.00 -90.00  110
 15  \w      8.00 104.00   1.00    1.00    --   69.25 -91.00   0.00   96
 16  \w    113.00 140.00   1.00    1.00    --   69.25 178.00   0.00   27
 17  \w    106.00 137.00   1.00    1.00    --   69.25 111.00 -30.00   31
 18  \w    101.00 172.00   1.00    2.40    --  113.72  32.00-150.00   71
 19  \w     44.00  86.00   1.00    2.40    --  113.72  32.00-150.00   42
 20  \w    109.00 178.00   1.00    2.40    --  113.72  77.00 120.00   69
 21  \w     25.00 100.00   1.00    2.40    --  113.72-104.00   0.00   75
 22  \w    104.00 174.00   1.00    2.40    --  113.72 104.00-150.00   70
 23  \w    128.00 176.00   1.00    2.40    --  113.72  77.00-180.00   48
 24  \w     91.00 125.00   1.00    2.40    --  113.72 138.00  60.00   34
 25  \w    115.00 161.00   1.00    2.40    --  113.72  77.00-120.00   46
 26  \w     50.00 107.00   1.00    2.40    --  113.72-104.00  60.00   57
 27  \w     76.00 154.00   1.00    2.40    --  113.72 -77.00 150.00   78
 28  \w    103.00 174.00   1.00    2.40    --  113.72  77.00 150.00   71
 29  \w     36.00  73.00   1.00    2.40    --  113.72 -77.00 150.00   37
 30  \w     38.00 103.00   1.00    2.40    --  113.72 -89.00 120.00   65
 31  \w    104.00 149.00   1.00    2.40    --  113.72  77.00 -90.00   45
 32  \w     50.00 144.00   1.00    2.40    --  113.72 -43.00 120.00   94
 33  \w    129.00 175.00   1.00    2.40    --  113.72 138.00  60.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0670632000
_diffrn_orient_matrix_UB_12      0.1303420000
_diffrn_orient_matrix_UB_13      0.0612429000
_diffrn_orient_matrix_UB_21      0.0424311000
_diffrn_orient_matrix_UB_22      0.1331785000
_diffrn_orient_matrix_UB_23      -0.0585765000
_diffrn_orient_matrix_UB_31      -0.2152931000
_diffrn_orient_matrix_UB_32      0.0429574000
_diffrn_orient_matrix_UB_33      -0.0320136000
_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  0.0683
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4921
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.530
_diffrn_reflns_theta_min         2.598
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.776
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       triclinic
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.268
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.1093
_refine_ls_R_factor_gt           0.0761
_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^)+(0.0570P)^2^+4.7052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2226
_refine_ls_wR_factor_ref         0.2541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2316
_reflns_number_total             3453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc05501b2.cif
_cod_data_source_block           gb_2562_rt_cu
_cod_depositor_comments          'Adding full bibliography for 7249880.cif.'
_cod_database_code               7249880
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C40  H36  Br2  N4  O2  P2'
_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:
 C12(H12), C6(H6), C5(H5), C9(H9), C11(H11), C19(H19), C2(H2), C10(H10),
 C3(H3), C16(H16), C18(H18), C17(H17)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              60469
_olex2_date_sample_data_collection 2023-07-17
_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 2.365
_oxdiff_exptl_absorpt_empirical_full_min 0.742