Room temperature stable <i>E</i>,<i>Z</i>-diphosphenes: their isomerization, coordination, and cycloaddition chemistry.
Lin, Jieli; Liu, Shihua; Zhang, Jie; Grützmacher, Hansjörg; Su, Cheng-Yong; Li, Zhongshu; Chemical science 14 (2023) 10944–10952; doi:10.1039/d3sc04506d

data_1569859
_publ_section_title
;
 Room temperature stable <i>E</i>,<i>Z</i>-diphosphenes: their
 isomerization, coordination, and cycloaddition chemistry.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10944
_journal_page_last               10952
_journal_paper_doi               10.1039/d3sc04506d
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C56 H78 N4 P2'
_chemical_formula_sum            'C56 H78 N4 P2'
_chemical_formula_weight         869.16
_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             2022-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-02 deposited with the CCDC.	2023-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                108.695(5)
_cell_angle_beta                 90.684(4)
_cell_angle_gamma                97.490(5)
_cell_formula_units_Z            4
_cell_length_a                   10.9009(6)
_cell_length_b                   20.4655(12)
_cell_length_c                   26.2304(11)
_cell_measurement_reflns_used    10351
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      25.9350
_cell_measurement_theta_min      2.5300
_cell_volume                     5486.8(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.22a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.22a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.22a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.896
_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     48.00  81.00   0.50   50.00    --    0.00  57.00  90.00   66
  2  \w    -88.00 -41.00   0.50   50.00    --    0.00 -19.00  60.00   94
  3  \w    -29.00  -3.00   0.50   50.00    --    0.00 -19.00  60.00   52
  4  \w    -16.00  88.00   0.50   50.00    --    0.00  57.00 -60.00  208
  5  \w    -15.00  33.00   0.50   50.00    --    0.00  38.00  60.00   96
  6  \w     61.00  87.00   0.50   50.00    --    0.00  38.00  60.00   52
  7  \w    -25.00  12.00   0.50   50.00    --    0.00  77.00 -30.00   74
  8  \w     48.00  75.00   0.50   50.00    --    0.00  77.00 -30.00   54
  9  \w    -16.00  81.00   0.50   50.00    --    0.00  38.00-150.00  194
 10  \w    -50.00 -25.00   0.50   50.00    --    0.00 -38.00-180.00   50
 11  \w    -88.00 -63.00   0.50   50.00    --    0.00 -19.00-150.00   50
 12  \w    -13.00  12.00   0.50   50.00    --    0.00 -19.00-150.00   50
 13  \w    -78.00 -53.00   0.50   50.00    --    0.00 -77.00   0.00   50
 14  \w    -15.00  28.00   0.50   50.00    --    0.00  57.00  90.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207395000
_diffrn_orient_matrix_UB_12      -0.0239518000
_diffrn_orient_matrix_UB_13      -0.0257608000
_diffrn_orient_matrix_UB_21      0.0078603000
_diffrn_orient_matrix_UB_22      -0.0281292000
_diffrn_orient_matrix_UB_23      0.0094095000
_diffrn_orient_matrix_UB_31      -0.0618811000
_diffrn_orient_matrix_UB_32      -0.0011081000
_diffrn_orient_matrix_UB_33      0.0080913000
_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  0.1663
_diffrn_reflns_av_unetI/netI     0.1573
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            124812
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.858
_diffrn_reflns_theta_min         2.756
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.22a (Rigaku Oxford Diffraction, 2019)
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    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.141
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1149
_refine_ls_number_reflns         28328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1833
_refine_ls_R_factor_gt           0.0728
_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^)+(0.0910P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.2030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12377
_reflns_number_total             28328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04506d2.cif
_cod_data_source_block           E-2b
_cod_depositor_comments
'Adding full bibliography for 1569855--1569860.cif.'
_cod_database_code               1569859
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C56 H78 N4 P2'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_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.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C26(H26), C29(H29), C38(H38), C41(H41), C52(H52),
 C55(H55), C70(H70), C73(H73), C82(H82), C85(H85), C96(H96), C99(H99),
 C108(H108), C111(H111)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C43(H43A,H43B), C44(H44A,H44B), C61(H61A,H61B),
 C62(H62A,H62B), C87(H87A,H87B), C88(H88A,H88B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C9(H9), C10(H10), C11(H11), C21(H21), C22(H22), C23(H23),
 C33(H33), C34(H34), C35(H35), C47(H47), C48(H48), C49(H49), C57(H57), C59(H59),
  C65(H65), C66(H66), C67(H67), C77(H77), C78(H78), C79(H79), C91(H91),
 C92(H92), C93(H93), C103(H103), C104(H104), C105(H105)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,
 H30B,H30C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C),
 C42(H42A,H42B,H42C), C51(H51A,H51B,H51C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C56(H56A,H56B,H56C), C69(H69A,H69B,H69C), C71(H71A,H71B,H71C), C72(H72A,
 H72B,H72C), C74(H74A,H74B,H74C), C81(H81A,H81B,H81C), C83(H83A,H83B,H83C),
 C84(H84A,H84B,H84C), C86(H86A,H86B,H86C), C95(H95A,H95B,H95C), C97(H97A,H97B,
 H97C), C98(H98A,H98B,H98C), C100(H10G,H10H,H10I), C107(H10D,H10E,H10F),
 C109(H10A,H10B,H10C), C110(H11D,H11E,H11F), C112(H11A,H11B,H11C)
;
_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 1.589
_oxdiff_exptl_absorpt_empirical_full_min 0.821