Coordination isomerism in dioxophosphorane cyanides
Nasrullah, Ayu Afiqah; Zander, Edgar; Dankert, Fabian; Petrov, Andrey; Surkau, Jonas; Baráth, Eszter; Hering-Junghans, Christian; Chemical Science 16 (2025) 6909–6917; doi:10.1039/D4SC07636B

data_1574151
_publ_section_title
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 Coordination isomerism in dioxophosphorane cyanides
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              6909
_journal_page_last               6917
_journal_paper_doi               10.1039/D4SC07636B
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C43 H61 N Na O8 P, 2(C7 H8)'
_chemical_formula_sum            'C57 H77 N Na O8 P'
_chemical_formula_weight         958.15
_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
_audit_creation_date             2025-02-04
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
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2025-02-27 deposited with the CCDC.	2025-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                91.519(2)
_cell_angle_beta                 99.269(2)
_cell_angle_gamma                99.707(2)
_cell_formula_units_Z            4
_cell_length_a                   10.4814(6)
_cell_length_b                   20.0122(12)
_cell_length_c                   26.3567(15)
_cell_measurement_reflns_used    9660
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.49
_cell_measurement_theta_min      2.27
_cell_volume                     5370.0(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            278986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.758
_diffrn_reflns_theta_min         1.034
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1565
_refine_ls_number_reflns         27880
_refine_ls_number_restraints     282
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0649P)^2^+2.7782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19778
_reflns_number_total             27880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07636b3.cif
_cod_data_source_block           ax2817_cmpd_3O2
_cod_depositor_comments
'Adding full bibliography for 1574150--1574157.cif.'
_cod_database_code               1574151
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C31, N1A}
{N1, C31A}
{N2, C74A}
{C74, N2A}
3. Restrained distances
 C121-C119 \\sim C121-C117
 with sigma of 0.002
 N1-C31 \\sim N1A-C31A
 with sigma of 0.02
 C67-C109 \\sim C71-C67
 with sigma of 0.002
 C73-C109 \\sim C71-C110 \\sim C111-C109 \\sim C72-C71
 with sigma of 0.002
 C87-C1F \\sim C89-C88
 with sigma of 0.002
 C1F-C1E \\sim C1F-C1D
 with sigma of 0.002
4. Rigid bond restraints
 C143, C138, C137, C142, C141, C140, C139
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C1A, C1B, C1C, C1D, C1E, C87, C1F, C121, C115, C116, C120, C117, C119, C118
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C1F, C1A, C1B, C1C, C1D, C1E, C87, C120, C115, C116, C117, C119, C118, C121,
 C107, C108, C89, C97, C88, C99, C98
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C71, C72, C110, C73, C109, C111
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Uiso/Uaniso restraints and constraints
Uanis(C121) \\sim Ueq, Uanis(C115) \\sim Ueq, Uanis(C116) \\sim Ueq,
Uanis(C120) \\sim Ueq, Uanis(C117) \\sim Ueq, Uanis(C119) \\sim Ueq,
Uanis(C118) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1C)
\\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C87) \\sim Ueq,
Uanis(C1F) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C143) \\sim Ueq, Uanis(C137) \\sim Ueq, Uanis(C138) \\sim Ueq,
Uanis(C139) \\sim Ueq, Uanis(C140) \\sim Ueq, Uanis(C142) \\sim Ueq,
Uanis(C141) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C115) \\sim Ueq, Uanis(C116) \\sim Ueq, Uanis(C120) \\sim Ueq,
Uanis(C117) \\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C118) \\sim Ueq,
Uanis(C121) \\sim Ueq, Uanis(C1F) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C1B)
\\sim Ueq, Uanis(C1C) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(C1E) \\sim Ueq,
Uanis(C87) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C107)
\\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C99) \\sim Ueq,
Uanis(C98) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C89) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C88)
\\sim Ueq, Uanis(C99) \\sim Ueq, Uanis(C98) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(C111) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C109)
\\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C110) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C74) = Uanis(N2A)
Uanis(N2) = Uanis(C74A)
Uanis(N1) = Uanis(C31A)
Uanis(N1A) = Uanis(C31)
Uanis(C31A) = Uanis(N1)
6. Others
 1*[Sof(C115)+Sof(H115)+Sof(C116)+Sof(H116)+Sof(C117)+Sof(H117)+Sof(C118)+
 Sof(C119)+Sof(H119)+Sof(C120)+Sof(H120)+Sof(C121)+Sof(H12A)+Sof(H12B)+
 Sof(H12C)]+1*[Sof(C1A)+Sof(H1A)+Sof(C1B)+Sof(H1B)+Sof(C1D)+Sof(H1D)+Sof(C87)+
 Sof(C1E)+Sof(H1E)+Sof(C1C)+Sof(H1C)+Sof(C1F)+Sof(H1FA)+Sof(H1FB)+Sof(H1FC)]+1*
 [Sof(C108)+Sof(H108)+Sof(C89)+Sof(C97)+Sof(H97)+Sof(C98)+Sof(H98)+Sof(C99)+
 Sof(H99)+Sof(C107)+Sof(H107)+Sof(C88)+Sof(H88A)+Sof(H88B)+Sof(H88C)]=1 with
 esd of 0.00001
 Sof(C139)=Sof(H139)=Sof(C138)=Sof(H138)=Sof(C137)=Sof(C142)=Sof(H142)=
 Sof(C141)=Sof(H141)=Sof(C140)=Sof(H140)=Sof(C143)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=1-FVAR(1)
 Sof(C130)=Sof(C131)=Sof(H131)=Sof(C132)=Sof(H132)=Sof(C133)=Sof(H133)=
 Sof(C134)=Sof(H134)=Sof(C135)=Sof(H135)=Sof(C136)=Sof(H13A)=Sof(H13B)=
 Sof(H13C)=FVAR(1)
 Sof(C115)=Sof(H115)=Sof(C116)=Sof(H116)=Sof(C117)=Sof(H117)=Sof(C118)=
 Sof(C119)=Sof(H119)=Sof(C120)=Sof(H120)=Sof(C121)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=FVAR(2)
 Sof(C1A)=Sof(H1A)=Sof(C1B)=Sof(H1B)=Sof(C1D)=Sof(H1D)=Sof(C87)=Sof(C1E)=
 Sof(H1E)=Sof(C1C)=Sof(H1C)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=FVAR(3)
 Sof(C108)=Sof(H108)=Sof(C89)=Sof(C97)=Sof(H97)=Sof(C98)=Sof(H98)=Sof(C99)=
 Sof(H99)=Sof(C107)=Sof(H107)=Sof(C88)=Sof(H88A)=Sof(H88B)=Sof(H88C)=FVAR(4)
 Sof(C71)=Sof(H71)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(H72C)=Sof(C110)=Sof(H11A)=
 Sof(H11B)=Sof(H11C)=1-FVAR(5)
 Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(H73C)=Sof(C109)=Sof(H109)=Sof(C111)=
 Sof(H11D)=Sof(H11E)=Sof(H11F)=FVAR(5)
 Sof(N1A)=Sof(C31A)=1-FVAR(6)
 Sof(N1)=Sof(C31)=FVAR(6)
 Sof(N2A)=Sof(C74A)=1-FVAR(7)
 Sof(N2)=Sof(C74)=FVAR(7)
7.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C25(H25), C28(H28), C56(H56), C59(H59), C68(H68),
 C71(H71), C109(H109)
7.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,
 H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B),
 C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C75(H75A,H75B), C76(H76A,H76B),
  C77(H77A,H77B), C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,
 H81B), C82(H82A,H82B), C83(H83A,H83B), C84(H84A,H84B), C85(H85A,H85B),
 C86(H86A,H86B)
7.c Me refined with riding coordinates:
 C96(H96A,H96B,H96C)
7.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C21(H21), C22(H22),
 C23(H23), C46(H46), C47(H47), C48(H48), C52(H52), C53(H53), C54(H54), C64(H64),
  C65(H65), C66(H66), C91(H91), C92(H92), C93(H93), C94(H94), C95(H95),
 C101(H101), C102(H102), C103(H103), C104(H104), C105(H105), C115(H115),
 C116(H116), C117(H117), C119(H119), C120(H120), C131(H131), C132(H132),
 C133(H133), C134(H134), C135(H135), C139(H139), C138(H138), C142(H142),
 C141(H141), C140(H140), C1A(H1A), C1B(H1B), C1D(H1D), C1E(H1E), C1C(H1C),
 C108(H108), C97(H97), C98(H98), C99(H99), C107(H107)
7.e Fitted hexagon refined as free rotating group:
 C115(C116,C117,C118,C119,C120), C130(C131,C132,C133,C134,C135), C139(C138,
 C137,C142,C141,C140), C1A(C1B,C1D,C87,C1E,C1C), C108(C89,C97,C98,C99,C107)
7.f Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,
 H30B,H30C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C),
 C61(H61A,H61B,H61C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C72(H72A,H72B,
 H72C), C106(H10A,H10B,H10C), C121(H12A,H12B,H12C), C136(H13A,H13B,H13C),
 C143(H14D,H14E,H14F), C1F(H1FA,H1FB,H1FC), C88(H88A,H88B,H88C), C110(H11A,H11B,
 H11C), C73(H73A,H73B,H73C), C111(H11D,H11E,H11F)
;
_shelx_res_checksum              10385
_olex2_submission_special_instructions 'No special instructions were received'