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_7251716
_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         'C24 H20 O P2 S2'
_chemical_formula_sum            'C24 H20 O P2 S2'
_chemical_formula_weight         450.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-21
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_audit_update_record
;
2025-08-29 deposited with the CCDC.	2026-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.675(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2303(11)
_cell_length_b                   9.0769(5)
_cell_length_c                   17.0558(13)
_cell_measurement_reflns_used    7157
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      30.3900
_cell_measurement_theta_min      2.5970
_cell_volume                     2159.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.101a 64-bit (release 13-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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     -5.00  50.00   0.50    0.50    --   -5.92  55.00 126.00  110
  2  \w    -18.00  26.00   0.50    0.50    --   -5.92 -99.00-150.00   88
  3  \w    -18.00  18.00   0.50    0.50    --   -5.92 -99.00 -90.00   72
  4  \w    -79.00   3.00   0.50    0.50    --   -5.92 -55.00 -16.00  164
  5  \w    -18.00  35.00   0.50    0.50    --    6.23 -99.00 150.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0019538000
_diffrn_orient_matrix_UB_12      0.0304677000
_diffrn_orient_matrix_UB_13      0.0389653000
_diffrn_orient_matrix_UB_21      -0.0417424000
_diffrn_orient_matrix_UB_22      0.0420008000
_diffrn_orient_matrix_UB_23      -0.0229651000
_diffrn_orient_matrix_UB_31      -0.0288776000
_diffrn_orient_matrix_UB_32      -0.0585096000
_diffrn_orient_matrix_UB_33      0.0038725000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8844
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         2.608
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0421P)^2^+1.8302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2001
_reflns_number_total             2193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6gc00879h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7251716--7251717.cif.'
_cod_database_code               7251716
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         chno
_cell_oxdiff_angle_alpha         89.958(3)
_cell_oxdiff_angle_beta          113.595(4)
_cell_oxdiff_angle_gamma         89.962(3)
_cell_oxdiff_length_a            15.2374(7)
_cell_oxdiff_length_b            9.0697(3)
_cell_oxdiff_length_c            17.0508(8)
_cell_oxdiff_measurement_reflns_used 7270
_cell_oxdiff_volume              2159.40(15)
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.938
_diffrn_oxdiff_digest_hkl
;
01dd9696f7d12ac9cd7654c1346dfad70db5ca
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C6(H6), C2(H2), C3(H3), C9(H9), C4(H4), C11(H11), C10(H10),
 C5(H5)
;
_shelx_res_checksum              91564
_shelx_hkl_checksum              32791
_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 1.281
_oxdiff_exptl_absorpt_empirical_full_min 0.781