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_1573086
_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         'C63 H82 N4 O P2'
_chemical_formula_sum            'C63 H82 N4 O P2'
_chemical_formula_weight         973.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-08 deposited with the CCDC.	2024-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5100(2)
_cell_length_b                   18.2431(3)
_cell_length_c                   30.1703(7)
_cell_measurement_reflns_used    9011
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.5540
_cell_measurement_theta_min      2.8120
_cell_volume                     5784.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.98a 64-bit (release 24-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_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    -77.00  30.00   0.50    2.00    --  -44.22  91.00 -17.00  214
  2  \w   -168.00-108.00   0.50    5.00    --  -97.00 -91.00 128.00  120
  3  \w   -165.00 -89.00   0.50    5.00    --  -97.00 -46.00 -18.00  152
  4  \w    -52.00 -25.00   0.50    5.00    --  -97.00  46.00 130.00   54
  5  \w   -113.00 -85.00   0.50    5.00    --  -97.00 -91.00-130.00   56
  6  \w    -18.00  18.00   0.50    2.00    --  -44.22  19.00 -90.00   72
  7  \w    -41.00  32.00   0.50    2.00    --  -44.22  38.00 -30.00  146
  8  \w    -11.00  16.00   0.50    2.00    --   44.22 -19.00-150.00   54
  9  \w   -112.00 -70.00   0.50    5.00    --  -97.00 125.00   0.00   84
 10  \w   -162.00 -97.00   0.50    5.00    --  -97.00-125.00  90.00  130
 11  \w    -51.00 -26.00   0.50    5.00    --  -97.00 125.00   0.00   50
 12  \w   -129.00 -94.00   0.50    5.00    --  -97.00 -45.00 -90.00   70
 13  \w    -50.00 -25.00   0.50    5.00    --  -97.00  45.00 -90.00   50
 14  \w   -112.00 -75.00   0.50    5.00    --  -97.00 125.00 150.00   74
 15  \w    -67.00 -30.00   0.50    5.00    --  -97.00 125.00 150.00   74
 16  \w   -169.00-143.00   0.50    5.00    --  -97.00 -45.00 -90.00   52
 17  \w     58.00 101.00   0.50    5.00    --  109.09 -77.00  30.00   86
 18  \w     36.00  62.00   0.50    5.00    --  109.09 -61.00 120.00   52
 19  \w     36.00  61.00   0.50    5.00    --  109.09 -61.00  60.00   50
 20  \w     36.00  67.00   0.50    5.00    --  109.09 -61.00 -30.00   62
 21  \w     43.00  68.00   0.50    5.00    --  109.09 -61.00-120.00   50
 22  \w     42.00  67.00   0.50    5.00    --  109.09 -61.00 -60.00   50
 23  \w     37.00  68.00   0.50    5.00    --  109.09 -61.00 -90.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0464411000
_diffrn_orient_matrix_UB_12      0.0772336000
_diffrn_orient_matrix_UB_13      0.0128845000
_diffrn_orient_matrix_UB_21      0.0693944000
_diffrn_orient_matrix_UB_22      0.0066444000
_diffrn_orient_matrix_UB_23      -0.0448319000
_diffrn_orient_matrix_UB_31      -0.1204476000
_diffrn_orient_matrix_UB_32      0.0335084000
_diffrn_orient_matrix_UB_33      -0.0207811000
_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  0.0622
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            33798
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.913
_diffrn_reflns_theta_min         2.831
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_description       prism
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 3181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     658
_refine_ls_number_reflns         11179
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0708
_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^)+(0.1005P)^2^+3.6723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1909
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                8923
_reflns_number_total             11179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06462c2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 1573084--1573090.cif.'
_cod_database_code               1573086
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.915
_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. Restrained distances
 C25-C26 \\sim C25A-C26
 with sigma of 0.02
3. Rigid bond restraints
 C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C18 \\sim C19: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
5. Others
 Sof(H26A)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(H26)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C23(H23), C26(H26A), C26(H26), C35(H35), C38(H38), C47(H47), C50(H50),
 C59(H59), C62(H62)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C18(H18), C19(H19),
 C20(H20), C30(H30), C31(H31), C32(H32), C42(H42), C43(H43), C44(H44), C54(H54),
  C55(H55), C56(H56)
6.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,
 H27C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C39(H39A,
 H39B,H39C), C46(H46A,H46B,H46C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C51(H51A,H51B,H51C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C61(H61A,H61B,
 H61C), C63(H63A,H63B,H63C), C25A(H25D,H25E,H25F)
;
_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 1.449
_oxdiff_exptl_absorpt_empirical_full_min 0.627