#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/82/7028240.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7028240
loop_
_publ_author_name
'Heift, Dominikus'
'Benkő, Zoltán'
'Grützmacher, Hansjörg'
_publ_section_title
;
 Coulomb repulsion versus cycloaddition: formation of anionic
 four-membered rings from sodium phosphaethynolate, Na(OCP).
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              831
_journal_page_last               840
_journal_paper_doi               10.1039/c3dt52359d
_journal_volume                  43
_journal_year                    2014
_chemical_formula_sum            'C54 H58 O10 P2'
_chemical_formula_weight         929.00
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                118.377(6)
_cell_angle_beta                 107.308(5)
_cell_angle_gamma                93.323(4)
_cell_formula_units_Z            1
_cell_length_a                   11.2018(6)
_cell_length_b                   11.2296(6)
_cell_length_c                   11.4596(6)
_cell_measurement_reflns_used    5243
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0555
_cell_measurement_theta_min      3.0743
_cell_volume                     1176.28(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    xp
_computing_publication_material  xp
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12035
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.6195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1592
_refine_ls_wR_factor_ref         0.1774
_reflns_number_gt                4268
_reflns_number_total             5378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52359d.txt
_cod_data_source_block           domdom1
_cod_original_cell_volume        1176.28(11)
_cod_database_code               7028240
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3979(2) 1.0355(2) 0.9859(2) 0.0305(5) Uani 1 1 d . . .
C2 C 0.46851(19) 0.9324(2) 0.7141(2) 0.0256(5) Uani 1 1 d . . .
C3 C 0.3370(2) 0.8647(2) 0.5903(2) 0.0253(5) Uani 1 1 d . . .
C4 C 0.32897(19) 0.7995(2) 0.4483(2) 0.0218(4) Uani 1 1 d . . .
H4 H 0.4052 0.7878 0.4280 0.026 Uiso 1 1 calc R . .
C3S C 0.9979(6) 0.7785(7) 0.9817(6) 0.0331(13) Uani 0.510(6) 1 d P A 1
H3S3 H 0.9263 0.8144 1.0101 0.040 Uiso 0.510(6) 1 calc PR A 1
H3S4 H 1.0724 0.8012 1.0676 0.040 Uiso 0.510(6) 1 calc PR A 1
C2S C 0.9569(7) 0.6231(6) 0.8718(7) 0.0354(14) Uani 0.510(6) 1 d P A 1
H2S3 H 0.9766 0.5686 0.9193 0.042 Uiso 0.510(6) 1 calc PR A 1
H2S4 H 0.8633 0.5946 0.8154 0.042 Uiso 0.510(6) 1 calc PR A 1
O1S O 1.0293(4) 0.6011(4) 0.7815(4) 0.0342(11) Uani 0.510(6) 1 d P A 1
C1S C 1.0679(4) 0.7299(4) 0.7901(5) 0.0269(11) Uani 0.510(6) 1 d P A 1
H1S3 H 1.1619 0.7540 0.8148 0.032 Uiso 0.510(6) 1 calc PR A 1
H1S4 H 1.0230 0.7240 0.6983 0.032 Uiso 0.510(6) 1 calc PR A 1
O1SB O 1.0862(4) 0.6931(4) 0.8569(5) 0.0359(12) Uani 0.490(6) 1 d P A 2
C1SB C 1.0142(7) 0.6009(7) 0.8768(8) 0.0395(16) Uani 0.490(6) 1 d P A 2
H1S1 H 1.0654 0.6013 0.9639 0.047 Uiso 0.490(6) 1 calc PR A 2
H1S2 H 0.9909 0.5048 0.7940 0.047 Uiso 0.490(6) 1 calc PR A 2
C2SB C 0.8951(6) 0.6511(6) 0.8911(6) 0.0344(13) Uani 0.490(6) 1 d P A 2
H2S1 H 0.8254 0.6125 0.7967 0.041 Uiso 0.490(6) 1 calc PR A 2
H2S2 H 0.8638 0.6267 0.9510 0.041 Uiso 0.490(6) 1 calc PR A 2
C3SB C 0.9431(8) 0.8047(7) 0.9622(9) 0.0514(19) Uani 0.490(6) 1 d P A 2
H3S1 H 0.8701 0.8482 0.9471 0.062 Uiso 0.490(6) 1 calc PR A 2
H3S2 H 0.9884 0.8459 1.0662 0.062 Uiso 0.490(6) 1 calc PR A 2
C4S C 1.0319(3) 0.8302(3) 0.9000(3) 0.0496(7) Uani 1 1 d . . .
H5S1 H 0.9577 0.8590 0.8566 0.059 Uiso 1 1 calc R A 1
H5S2 H 1.1043 0.9137 0.9648 0.059 Uiso 1 1 calc R A 1
C5 C 0.2112(2) 0.7520(2) 0.3374(2) 0.0247(4) Uani 1 1 d . . .
H5 H 0.2077 0.7083 0.2418 0.030 Uiso 1 1 calc R . .
C6 C 0.0987(2) 0.7671(2) 0.3635(2) 0.0328(5) Uani 1 1 d . . .
C7 C 0.1041(2) 0.8277(3) 0.5039(3) 0.0497(8) Uani 1 1 d . . .
H7 H 0.0274 0.8359 0.5236 0.060 Uiso 1 1 calc R . .
C8 C 0.2229(2) 0.8758(3) 0.6144(2) 0.0441(7) Uani 1 1 d . . .
H8 H 0.2261 0.9178 0.7097 0.053 Uiso 1 1 calc R . .
C9 C -0.1291(2) 0.7369(5) 0.2693(3) 0.0817(14) Uani 1 1 d . . .
H9A H -0.1227 0.8356 0.3339 0.123 Uiso 1 1 calc R . .
H9B H -0.1462 0.6830 0.3116 0.123 Uiso 1 1 calc R . .
H9C H -0.1994 0.7031 0.1777 0.123 Uiso 1 1 calc R . .
C10 C 0.57168(19) 0.8585(2) 0.6698(2) 0.0228(4) Uani 1 1 d . . .
C11 C 0.67316(19) 0.9212(2) 0.6554(3) 0.0301(5) Uani 1 1 d . . .
H11 H 0.6840 1.0163 0.6816 0.036 Uiso 1 1 calc R . .
C12 C 0.7577(2) 0.8477(3) 0.6039(4) 0.0490(8) Uani 1 1 d . . .
H12 H 0.8263 0.8931 0.5957 0.059 Uiso 1 1 calc R . .
C13 C 0.7453(2) 0.7085(3) 0.5637(3) 0.0385(6) Uani 1 1 d . . .
C14 C 0.6469(2) 0.6449(2) 0.5802(2) 0.0283(5) Uani 1 1 d . . .
H14 H 0.6376 0.5505 0.5562 0.034 Uiso 1 1 calc R . .
C15 C 0.5625(2) 0.7199(2) 0.6318(2) 0.0316(5) Uani 1 1 d . . .
H15 H 0.4951 0.6749 0.6418 0.038 Uiso 1 1 calc R . .
C16 C 0.8145(3) 0.4975(3) 0.4546(4) 0.0552(9) Uani 1 1 d . . .
H16A H 0.7266 0.4486 0.3853 0.083 Uiso 1 1 calc R . .
H16B H 0.8301 0.4801 0.5334 0.083 Uiso 1 1 calc R . .
H16C H 0.8758 0.4634 0.4078 0.083 Uiso 1 1 calc R . .
C17 C 0.5049(2) 1.0898(2) 0.7750(2) 0.0266(5) Uani 1 1 d . . .
C18 C 0.4308(2) 1.1544(2) 0.7148(2) 0.0292(5) Uani 1 1 d . . .
H18 H 0.3522 1.1005 0.6361 0.035 Uiso 1 1 calc R . .
C19 C 0.4674(2) 1.2965(2) 0.7655(2) 0.0311(5) Uani 1 1 d . . .
H19 H 0.4145 1.3379 0.7212 0.037 Uiso 1 1 calc R . .
C20 C 0.5812(2) 1.3762(2) 0.8806(2) 0.0340(6) Uani 1 1 d . . .
C21 C 0.6562(2) 1.3143(3) 0.9458(2) 0.0407(7) Uani 1 1 d . . .
H21 H 0.7333 1.3691 1.0267 0.049 Uiso 1 1 calc R . .
C22 C 0.6189(2) 1.1738(3) 0.8935(2) 0.0350(6) Uani 1 1 d . . .
H22 H 0.6715 1.1328 0.9385 0.042 Uiso 1 1 calc R . .
C23 C 0.5663(3) 1.5755(3) 0.8593(3) 0.0487(7) Uani 1 1 d . . .
H23A H 0.4796 1.5773 0.8614 0.073 Uiso 1 1 calc R . .
H23B H 0.5604 1.5205 0.7601 0.073 Uiso 1 1 calc R . .
H23C H 0.6156 1.6709 0.9029 0.073 Uiso 1 1 calc R . .
O1 O 0.29792(17) 1.07169(17) 0.97147(16) 0.0357(4) Uani 1 1 d . . .
O2 O -0.01071(15) 0.7210(2) 0.24672(17) 0.0414(5) Uani 1 1 d . . .
O3 O 0.83075(18) 0.6439(2) 0.5092(3) 0.0748(9) Uani 1 1 d . . .
O4 O 0.62891(19) 1.51469(18) 0.93659(17) 0.0443(5) Uani 1 1 d . . .
P1 P 0.45094(6) 0.89620(6) 0.85542(6) 0.02992(19) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 C1 P1 131.14(17) . .
O1 C1 P1 131.27(18) . 2_677
P1 C1 P1 97.58(13) . 2_677
C10 C2 C17 113.22(16) . .
C10 C2 C3 111.15(17) . .
C17 C2 C3 110.94(18) . .
C10 C2 P1 104.75(14) . .
C17 C2 P1 110.43(13) . .
C3 C2 P1 105.94(13) . .
C8 C3 C4 117.55(19) . .
C8 C3 C2 121.59(18) . .
C4 C3 C2 120.65(18) . .
C5 C4 C3 120.72(19) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4S C3S C2S 99.8(4) . .
C4S C3S H3S3 111.8 . .
C2S C3S H3S3 111.8 . .
C4S C3S H3S4 111.8 . .
C2S C3S H3S4 111.8 . .
H3S3 C3S H3S4 109.5 . .
O1S C2S C3S 105.7(4) . .
O1S C2S H2S3 110.6 . .
C3S C2S H2S3 110.6 . .
O1S C2S H2S4 110.6 . .
C3S C2S H2S4 110.6 . .
H2S3 C2S H2S4 108.7 . .
C1S O1S C2S 108.7(4) . .
C4S C1S O1S 104.7(4) . .
C4S C1S H1S3 110.8 . .
O1S C1S H1S3 110.8 . .
C4S C1S H1S4 110.8 . .
O1S C1S H1S4 110.8 . .
H1S3 C1S H1S4 108.9 . .
C1SB O1SB C4S 108.5(4) . .
O1SB C1SB C2SB 107.1(5) . .
O1SB C1SB H1S1 110.3 . .
C2SB C1SB H1S1 110.3 . .
O1SB C1SB H1S2 110.3 . .
C2SB C1SB H1S2 110.3 . .
H1S1 C1SB H1S2 108.5 . .
C3SB C2SB C1SB 101.5(5) . .
C3SB C2SB H2S1 111.5 . .
C1SB C2SB H2S1 111.5 . .
C3SB C2SB H2S2 111.5 . .
C1SB C2SB H2S2 111.5 . .
H2S1 C2SB H2S2 109.3 . .
C4S C3SB C2SB 108.2(5) . .
C4S C3SB H3S1 110.0 . .
C2SB C3SB H3S1 110.0 . .
C4S C3SB H3S2 110.0 . .
C2SB C3SB H3S2 110.0 . .
H3S1 C3SB H3S2 108.4 . .
C1S C4S C3S 112.8(4) . .
C1S C4S C3SB 127.8(4) . .
C3S C4S C3SB 28.6(3) . .
C1S C4S O1SB 38.5(2) . .
C3S C4S O1SB 77.1(3) . .
C3SB C4S O1SB 100.2(4) . .
C1S C4S H5S1 109.0 . .
C3S C4S H5S1 109.0 . .
C3SB C4S H5S1 80.7 . .
O1SB C4S H5S1 137.4 . .
C1S C4S H5S2 109.0 . .
C3S C4S H5S2 109.0 . .
C3SB C4S H5S2 116.4 . .
O1SB C4S H5S2 109.5 . .
H5S1 C4S H5S2 107.8 . .
C6 C5 C4 120.97(19) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
O2 C6 C5 115.83(19) . .
O2 C6 C7 125.0(2) . .
C5 C6 C7 119.2(2) . .
C8 C7 C6 119.3(2) . .
C8 C7 H7 120.4 . .
C6 C7 H7 120.4 . .
C3 C8 C7 122.2(2) . .
C3 C8 H8 118.9 . .
C7 C8 H8 118.9 . .
O2 C9 H9A 109.5 . .
O2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
O2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C15 C10 C11 116.6(2) . .
C15 C10 C2 120.49(18) . .
C11 C10 C2 122.78(19) . .
C12 C11 C10 121.0(2) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C11 C12 C13 121.5(2) . .
C11 C12 H12 119.2 . .
C13 C12 H12 119.2 . .
O3 C13 C14 124.6(2) . .
O3 C13 C12 116.9(2) . .
C14 C13 C12 118.5(2) . .
C15 C14 C13 119.4(2) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
C14 C15 C10 123.01(19) . .
C14 C15 H15 118.5 . .
C10 C15 H15 118.5 . .
O3 C16 H16A 109.5 . .
O3 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O3 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 C22 117.1(2) . .
C18 C17 C2 122.22(18) . .
C22 C17 C2 120.6(2) . .
C17 C18 C19 122.2(2) . .
C17 C18 H18 118.9 . .
C19 C18 H18 118.9 . .
C20 C19 C18 119.5(2) . .
C20 C19 H19 120.3 . .
C18 C19 H19 120.3 . .
O4 C20 C19 124.8(2) . .
O4 C20 C21 115.7(2) . .
C19 C20 C21 119.5(2) . .
C22 C21 C20 120.1(2) . .
C22 C21 H21 119.9 . .
C20 C21 H21 119.9 . .
C21 C22 C17 121.6(2) . .
C21 C22 H22 119.2 . .
C17 C22 H22 119.2 . .
O4 C23 H23A 109.5 . .
O4 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
O4 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C6 O2 C9 117.66(19) . .
C13 O3 C16 118.8(2) . .
C20 O4 C23 117.13(19) . .
C1 P1 C1 82.41(13) . 2_677
C1 P1 C2 112.67(10) . .
C1 P1 C2 113.29(9) 2_677 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.205(3) .
C1 P1 1.858(3) .
C1 P1 1.859(2) 2_677
C2 C10 1.530(3) .
C2 C17 1.534(3) .
C2 C3 1.537(3) .
C2 P1 1.906(2) .
C3 C8 1.386(3) .
C3 C4 1.402(3) .
C4 C5 1.385(3) .
C4 H4 0.9500 .
C3S C4S 1.436(7) .
C3S C2S 1.522(8) .
C3S H3S3 0.9900 .
C3S H3S4 0.9900 .
C2S O1S 1.439(8) .
C2S H2S3 0.9900 .
C2S H2S4 0.9900 .
O1S C1S 1.434(5) .
C1S C4S 1.423(5) .
C1S H1S3 0.9900 .
C1S H1S4 0.9900 .
O1SB C1SB 1.417(8) .
O1SB C4S 1.597(5) .
C1SB C2SB 1.501(9) .
C1SB H1S1 0.9900 .
C1SB H1S2 0.9900 .
C2SB C3SB 1.492(9) .
C2SB H2S1 0.9900 .
C2SB H2S2 0.9900 .
C3SB C4S 1.470(8) .
C3SB H3S1 0.9900 .
C3SB H3S2 0.9900 .
C4S H5S1 0.9900 .
C4S H5S2 0.9900 .
C5 C6 1.381(3) .
C5 H5 0.9500 .
C6 O2 1.362(3) .
C6 C7 1.397(3) .
C7 C8 1.389(3) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 O2 1.430(3) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C15 1.391(3) .
C10 C11 1.394(3) .
C11 C12 1.374(4) .
C11 H11 0.9500 .
C12 C13 1.388(3) .
C12 H12 0.9500 .
C13 O3 1.356(3) .
C13 C14 1.387(3) .
C14 C15 1.379(3) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 O3 1.431(3) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 C18 1.376(3) .
C17 C22 1.406(3) .
C18 C19 1.398(3) .
C18 H18 0.9500 .
C19 C20 1.382(3) .
C19 H19 0.9500 .
C20 O4 1.366(3) .
C20 C21 1.391(4) .
C21 C22 1.378(3) .
C21 H21 0.9500 .
C22 H22 0.9500 .
C23 O4 1.416(3) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
P1 C1 1.859(2) 2_677
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139162994
