Catalyst-free synthesis of phosphinochalcogenoic anhydrides via the oxygen–chalcogen exchange with elemental sulfur or selenium
Zhu, Longzhi; Xie, Shuangjiao; Yang, Hongbo; Hong, Yingle; Chen, Lin; Luo, Weiwei; Jin, Sha; Liu, Lixin; Xiong, Biquan; Green Chemistry 28 (2026) 5848–5856; doi:10.1039/D6GC00879H

data_7251717
_publ_section_title
;
 Catalyst-free synthesis of phosphinochalcogenoic anhydrides via the
 oxygen--chalcogen exchange with elemental sulfur or selenium
;
_journal_issue                   13
_journal_name_full               'Green Chemistry'
_journal_page_first              5848
_journal_page_last               5856
_journal_paper_doi               10.1039/D6GC00879H
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C28 H21 O2 P Se'
_chemical_formula_sum            'C28 H21 O2 P Se'
_chemical_formula_weight         499.38
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2025-10-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-10-22 deposited with the CCDC.	2026-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5224(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.20299(15)
_cell_length_b                   13.2426(2)
_cell_length_c                   16.7176(3)
_cell_measurement_reflns_used    7207
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      72.2910
_cell_measurement_theta_min      4.2350
_cell_volume                     2257.99(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.962
_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     56.00  88.00   0.50    0.19    --   62.22  15.00 120.00   64
  2  \w     65.00 101.00   0.50    0.19    --   62.22  15.00  60.00   72
  3  \w     59.00 101.00   0.50    0.19    --   62.22  15.00 -90.00   84
  4  \w     74.00 109.00   0.50    0.19    --   71.24  15.00-120.00   70
  5  \w     69.00  95.00   0.50    0.19    --   62.22  15.00-180.00   52
  6  \w     74.00 100.00   0.50    0.19    --   74.35  15.00-150.00   52
  7  \w     59.00  91.00   0.50    0.19    --   62.22  15.00-120.00   64
  8  \w     67.00 106.00   0.50    0.19    --   74.35  15.00-180.00   78
  9  \w     56.00  99.00   0.50    0.19    --   62.22  15.00 -30.00   86
 10  \w     71.00  97.00   0.50    0.19    --   74.35  15.00 -60.00   52
 11  \w     86.00 112.00   0.50    0.19    --   74.35  15.00 -30.00   52
 12  \w     67.00 115.00   0.50    0.19    --   74.35  15.00  60.00   96
 13  \w     71.00 112.00   0.50    0.19    --   74.35  15.00 120.00   82
 14  \w     38.00  64.00   0.50    0.19    --   74.35-125.00   0.00   52
 15  \w     42.00  69.00   0.50    0.19    --   62.22-125.00 -30.00   54
 16  \w     32.00  75.00   0.50    0.19    --   62.22-125.00 -90.00   86
 17  \w     45.00  76.00   0.50    0.19    --   62.22-125.00-120.00   62
 18  \w     49.00  75.00   0.50    0.19    --   62.22-125.00-180.00   52
 19  \w     44.00  87.00   0.50    0.19    --   71.24-125.00-120.00   86
 20  \w     51.00  89.00   0.50    0.19    --   74.35-125.00 -90.00   76
 21  \w     54.00  79.00   0.50    0.19    --   74.35-125.00 -60.00   50
 22  \w     64.00  89.00   0.50    0.19    --   74.35-125.00-120.00   50
 23  \w     38.00  89.00   0.50    0.19    --   74.35-125.00-180.00  102
 24  \w     38.00  90.00   0.50    0.19    --   74.35-125.00-150.00  104
 25  \w     25.00  73.00   0.50    0.19    --   62.22-125.00  90.00   96
 26  \w     25.00  70.00   0.50    0.19    --   62.22-125.00 150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0172487000
_diffrn_orient_matrix_UB_12      -0.1083070000
_diffrn_orient_matrix_UB_13      0.0316996000
_diffrn_orient_matrix_UB_21      -0.1152283000
_diffrn_orient_matrix_UB_22      -0.0165454000
_diffrn_orient_matrix_UB_23      -0.0599983000
_diffrn_orient_matrix_UB_31      0.0962617000
_diffrn_orient_matrix_UB_32      -0.0388585000
_diffrn_orient_matrix_UB_33      -0.0624107000
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17321
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.941
_diffrn_reflns_theta_min         4.260
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0311P)^2^+1.6914P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3723
_reflns_number_total             4341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6gc00879h2.cif
_cod_data_source_block           44166_se
_cod_depositor_comments
'Adding full bibliography for 7251716--7251717.cif.'
_cod_original_cell_volume        2258.00(6)
_cod_database_code               7251717
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Se P'
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
  C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.811