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_1569855
_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         '2(C58 H82 N4 P2), C5 H12'
_chemical_formula_sum            'C121 H176 N8 P4'
_chemical_formula_weight         1866.57
_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                65.623(2)
_cell_angle_beta                 86.626(2)
_cell_angle_gamma                86.202(2)
_cell_formula_units_Z            1
_cell_length_a                   10.8467(3)
_cell_length_b                   15.6202(4)
_cell_length_c                   18.4959(4)
_cell_measurement_reflns_used    18783
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1460
_cell_measurement_theta_min      2.9120
_cell_volume                     2846.36(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.899
_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    -81.00 -56.00   0.50   50.00    --    0.00 -19.00 120.00   50
  2  \w    -20.00  18.00   0.50   50.00    --    0.00 -19.00 120.00   76
  3  \w    -71.00 -45.00   0.50   50.00    --    0.00 -82.00 120.00   52
  4  \w     27.00  88.00   0.50   50.00    --    0.00  77.00   0.00  122
  5  \w    -27.00  31.00   0.50   50.00    --    0.00  77.00  60.00  116
  6  \w     47.00  73.00   0.50   50.00    --    0.00  77.00  60.00   52
  7  \w    -28.00   3.00   0.50   50.00    --    0.00  77.00 120.00   62
  8  \w     19.00  89.00   0.50   50.00    --    0.00  77.00 120.00  140
  9  \w    -89.00 -58.00   0.50   50.00    --    0.00 -77.00  30.00   62
 10  \w    -55.00 -29.00   0.50   50.00    --    0.00 -77.00  30.00   52
 11  \w     13.00  45.00   0.50   50.00    --    0.00  38.00 -30.00   64
 12  \w     24.00  88.00   0.50   50.00    --    0.00  19.00  90.00  128
 13  \w    -28.00  -1.00   0.50   50.00    --    0.00  77.00-180.00   54
 14  \w    -40.00 -12.00   0.50   50.00    --    0.00 -77.00  60.00   56
;
_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      -0.0458250000
_diffrn_orient_matrix_UB_12      0.0150783000
_diffrn_orient_matrix_UB_13      -0.0290741000
_diffrn_orient_matrix_UB_21      0.0146599000
_diffrn_orient_matrix_UB_22      0.0474463000
_diffrn_orient_matrix_UB_23      -0.0110402000
_diffrn_orient_matrix_UB_31      0.0445579000
_diffrn_orient_matrix_UB_32      -0.0034920000
_diffrn_orient_matrix_UB_33      -0.0284179000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            61291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.963
_diffrn_reflns_theta_min         2.866
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_description       plate
_exptl_crystal_F_000             1018
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         14866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+0.6042P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11134
_reflns_number_total             14866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04506d2.cif
_cod_data_source_block           E-2a
_cod_depositor_comments
'Adding full bibliography for 1569855--1569860.cif.'
_cod_database_code               1569855
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.983
_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: C63(0.5) H63A(0.5) H63B(0.5) H63C(0.5) C59(0.5) H59A(0.5)
 H59B(0.5) H59C(0.5) C60(0.5) H60A(0.5) H60B(0.5) C61(0.5) H61A(0.5) H61B(0.5)
 C62(0.5) H62A(0.5) H62B(0.5)
3.a Free rotating group:
 C63(C59,C60,C61,C62)
3.b Ternary CH refined with riding coordinates:
 C16(H16), C19(H19), C28(H28), C31(H31), C42(H42), C45(H45), C54(H54), C57(H57)
3.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C33(H33A,H33B), C34(H34A,H34B), C60(H60A,H60B),
 C61(H61A,H61B), C62(H62A,H62B)
3.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C23(H23), C24(H24), C25(H25), C37(H37),
 C38(H38), C39(H39), C49(H49), C50(H50), C51(H51)
3.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C32(H32A,H32B,H32C), C6(H6A,H6B,H6C), C41(H41A,H41B,H41C),
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C53(H53A,H53B,
 H53C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C63(H63A,
 H63B,H63C), C59(H59A,H59B,H59C)
;
_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 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.820