Diphosphaenones: beyond the phosphorus analogue of enones.
Lin, Jieli; Liu, Shihua; Zheng, Shunlin; Grützmacher, Hansjörg; Su, Cheng-Yong; Li, Zhongshu; Chemical science 15 (2024) 20030–20038; doi:10.1039/d4sc06462c

data_1573087
_publ_section_title
;
 Diphosphaenones: beyond the phosphorus analogue of enones.
;
_journal_issue                   47
_journal_name_full               'Chemical science'
_journal_page_first              20030
_journal_page_last               20038
_journal_paper_doi               10.1039/d4sc06462c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C F3 O3 S, C57 H81 N4 P2, 2(C6 H5 F), C3 H2 F'
_chemical_formula_sum            'C73 H93 F6 N4 O3 P2 S'
_chemical_formula_weight         1282.51
_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             2024-09-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-22 deposited with the CCDC.	2024-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                79.7010(10)
_cell_angle_beta                 86.7710(10)
_cell_angle_gamma                80.6750(10)
_cell_formula_units_Z            2
_cell_length_a                   13.0834(2)
_cell_length_b                   13.3184(2)
_cell_length_c                   20.9406(3)
_cell_measurement_reflns_used    34115
_cell_measurement_temperature    149.9(6)
_cell_measurement_theta_max      72.6990
_cell_measurement_theta_min      3.3980
_cell_volume                     3541.26(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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    -71.00  31.00   1.00    2.50    --    2.00 -60.00 128.64  102
  2  \w     -4.00  21.00   1.00    2.50    --   34.00  91.00 120.65   25
  3  \w      2.00  27.00   1.00    2.50    --   38.00  87.00  -4.64   25
  4  \w      1.00  27.00   1.00    2.50    --   38.00  89.00-117.99   26
  5  \w    -87.00  -6.00   1.00    2.50    --  -40.70 125.00 150.00   81
  6  \w   -114.00 -15.00   1.00    2.50    --  -40.70 -57.00  60.00   99
  7  \w    -61.00  31.00   1.00    2.50    --  -40.70  38.00 150.00   92
  8  \w    -87.00  -6.00   1.00    2.50    --  -40.70 125.00 -30.00   81
  9  \w     16.00  41.00   1.00    2.50    --   50.00  82.00  81.95   25
 10  \w     16.00  41.00   1.00    2.50    --   50.00  81.00 148.70   25
 11  \w     16.00  41.00   1.00    2.50    --   50.00  82.00  26.82   25
 12  \w     16.00  42.00   1.00    2.50    --   50.00  82.00-101.66   26
 13  \w     16.00  41.00   1.00    2.50    --   50.00  81.00 -38.85   25
 14  \w     16.00  42.00   1.00    2.50    --   50.00  82.00-166.14   26
 15  \w     32.00  58.00   1.00    2.50    --   62.00  69.00 -67.48   26
 16  \w     35.00  61.00   1.00    2.50    --   66.00  71.00 119.16   26
 17  \w     38.00  64.00   1.00    2.50    --   66.00  69.00 -40.64   26
 18  \w     35.00  65.00   1.00    2.50    --   66.00  70.00-121.37   30
 19  \w     39.00  99.00   1.00    2.50    --   70.00  71.00  26.27   60
 20  \w     39.00  65.00   1.00    2.50    --   70.00  70.00  74.70   26
 21  \w    100.00 141.00   1.00    2.50    --   70.00  70.00  74.70   41
 22  \w     39.00  92.00   1.00    2.50    --   70.00  71.00 -12.72   53
 23  \w     45.00  70.00   1.00    5.00    --   74.00  61.00 -89.41   25
 24  \w     43.00  69.00   1.00    5.00    --   74.00  69.00 133.63   26
 25  \w     52.00  78.00   1.00    5.00    --   78.00  59.00  82.94   26
 26  \w     48.00 113.00   1.00    5.00    --   78.00  68.00-170.26   65
 27  \w     47.00  77.00   1.00    5.00    --   78.00  70.00 167.01   30
 28  \w     47.00  73.00   1.00    5.00    --   78.00  71.00 -79.73   26
 29  \w     52.00  78.00   1.00    5.00    --   82.00  64.00 147.55   26
 30  \w     55.00  81.00   1.00    5.00    --   86.00  70.00 -65.13   26
 31  \w    125.00 152.00   1.00    5.00    --   90.00  69.00  82.50   27
 32  \w     59.00  95.00   1.00    5.00    --   90.00  71.00  -0.46   36
 33  \w     59.00  85.00   1.00    5.00    --   90.00  69.00  82.50   26
 34  \w     64.00  90.00   1.00    5.00    --   94.00  66.00 177.15   26
 35  \w    115.00 151.00   1.00    5.00    --   94.00  68.00 -38.42   36
 36  \w     64.00 103.00   1.00    5.00    --   94.00  68.00 -38.42   39
 37  \w     65.00 162.00   1.00    5.00    --   94.00  62.00 117.79   97
 38  \w     65.00 145.00   1.00    5.00    --   94.00  61.00-137.16   80
 39  \w    116.00 162.00   1.00    5.00    --   98.00  68.00-120.10   46
 40  \w     68.00  94.00   1.00    5.00    --   98.00  68.00-120.10   26
 41  \w    127.00 167.00   1.00    5.00    --  102.00  55.00  54.49   40
 42  \w     75.00 111.00   1.00    5.00    --  102.00  55.00  54.49   36
 43  \w     30.00 105.00   1.00    5.00    --  104.23 -94.00-120.00   75
 44  \w     39.00 107.00   1.00    5.00    --  104.23-101.00  46.30   68
 45  \w    112.00 170.00   1.00    5.00    --  104.23  61.00 -90.00   58
 46  \w     75.00 106.00   1.00    5.00    --  104.23  61.00 -90.00   31
 47  \w     75.00 176.00   1.00    5.00    --  104.23  60.00  87.52  101
 48  \w     79.00 176.00   1.00    5.00    --  104.23  65.00 178.14   97
 49  \w     34.00 112.00   1.00    5.00    --  104.23-125.00-120.00   78
 50  \w     75.00 167.00   1.00    5.00    --  104.23  61.00 150.00   92
 51  \w     87.00 112.00   1.00    5.00    --  104.23-125.00 120.00   25
 52  \w     37.00  75.00   1.00    5.00    --  104.23-125.00 120.00   38
 53  \w    122.00 169.00   1.00    5.00    --  104.23  61.00  30.00   47
 54  \w     75.00 101.00   1.00    5.00    --  104.23  61.00  30.00   26
 55  \w     81.00 110.00   1.00    5.00    --  104.23-125.00  30.00   29
 56  \w     75.00 162.00   1.00    5.00    --  104.23  61.00   0.00   87
 57  \w     53.00 129.00   1.00    5.00    --  104.23 -61.00  60.00   76
 58  \w     75.00 163.00   1.00    5.00    --  104.23  61.00 -60.00   88
 59  \w     36.00 130.00   1.00    5.00    --  104.23 -61.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297880000
_diffrn_orient_matrix_UB_12      -0.0595349000
_diffrn_orient_matrix_UB_13      0.0681174000
_diffrn_orient_matrix_UB_21      -0.1139637000
_diffrn_orient_matrix_UB_22      -0.0136328000
_diffrn_orient_matrix_UB_23      0.0154647000
_diffrn_orient_matrix_UB_31      0.0193655000
_diffrn_orient_matrix_UB_32      -0.1021295000
_diffrn_orient_matrix_UB_33      -0.0267637000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            63032
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.687
_diffrn_reflns_theta_min         3.414
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             1366
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.990
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     828
_refine_ls_number_reflns         13789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0975P)^2^+2.6149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1743
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12095
_reflns_number_total             13789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06462c2.cif
_cod_data_source_block           14
_cod_depositor_comments
'Adding full bibliography for 1573084--1573090.cif.'
_cod_database_code               1573087
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H65(0.5) H66(0.5) F6(0.5) F7(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15), C18(H18), C27(H27), C30(H30), C41(H41), C44(H44), C53(H53),
 C56(H56)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C32(H32A,H32B), C33(H33A,H33B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C11(H11), C12(H12), C22(H22), C23(H23), C24(H24), C36(H36),
 C37(H37), C38(H38), C48(H48), C49(H49), C50(H50), C65(H65), C66(H66), C67(H67),
  C68(H68), C69(H69), C70(H70), C71(H71), C72(H72), C59(H59), C60(H60),
 C61(H61), C62(H62), C63(H63)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,
 H29B,H29C), C31(H31A,H31B,H31C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C),
 C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C52(H52A,H52B,H52C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C)
;
_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 1.195
_oxdiff_exptl_absorpt_empirical_full_min 0.902