##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-05-01
_journal_date_accepted     2010-05-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1625
_journal_page_last     o1625
_journal_paper_category     QO
_journal_coeditor_code     BQ2208
_publ_contact_author_name     'Debashis Chakraborty'
_publ_contact_author_address
;
      Department of Chemistry
      IIT Madras, Chennai
      TamilNadu
      India
;
_publ_contact_author_email     dchakraborty@iitm.ac.in
_publ_contact_author_fax     '  '
_publ_contact_author_phone     '+91-44-22574223'
_publ_section_title
;
Triethylammonium 1,1'-binaphthyl-2,2'-diyl phosphate
;
loop_
    _publ_author_name
    _publ_author_address
    'Ravikumar R. Gowda'
;      Department of Chemistry
      IIT Madras, Chennai
      TamilNadu
      India
;
    'Venkatachalam Ramkumar'
;     Department of Chemistry
      IIT Madras, Chennai
      TamilNadu
      India
;
    'Debashis Chakraborty'
;     Department of Chemistry
      IIT Madras, Chennai
      TamilNadu
      India
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Triethylammonium 1,1'-binaphthyl-2,2'-diyl phosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H16 N+, C20 H12 O4 P -'
_chemical_formula_sum     'C26 H28 N O4 P'
_chemical_formula_iupac     'C6 H16 N+, C20 H12 O4 P -'
_chemical_formula_weight     449.46
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab '
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     8.4605(2)
_cell_length_b     13.3603(4)
_cell_length_c     20.5688(7)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2324.99(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7503
_cell_measurement_theta_min     2.50
_cell_measurement_theta_max     27.92
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.284
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     952
_exptl_absorpt_coefficient_mu     0.151
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1999)'
_exptl_absorpt_correction_T_min     0.9534
_exptl_absorpt_correction_T_max     0.9676
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     30327
_diffrn_reflns_av_R_equivalents     0.0278
_diffrn_reflns_av_sigmaI/netI     0.0244
_diffrn_reflns_theta_min     2.50
_diffrn_reflns_theta_max     28.25
_diffrn_reflns_theta_full     28.25
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     5561
_reflns_number_gt     4823
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0517
_refine_ls_R_factor_gt     0.0430
_refine_ls_wR_factor_gt     0.1144
_refine_ls_wR_factor_ref     0.1209
_refine_ls_goodness_of_fit_ref     1.042
_refine_ls_restrained_S_all     1.042
_refine_ls_number_reflns     5561
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0768P)²+0.3083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.542
_refine_diff_density_min     -0.305
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.000
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     0.50(10)
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'
    'N' 'N' 0.0061 0.0033
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'APEX2 and SAINT-Plus (Bruker, 2004)'
_computing_data_reduction     'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.9569(2) -0.09228(15) 0.66118(9) 0.0337(4) Uani d . 1 . .
    C C2 1.0264(3) -0.18489(16) 0.67555(11) 0.0431(5) Uani d . 1 . .
    H H2 0.9953 -0.2203 0.7123 0.052 Uiso calc R 1 . .
    C C3 1.1397(3) -0.22298(15) 0.63547(12) 0.0475(5) Uani d . 1 . .
    H H3 1.1837 -0.2853 0.6444 0.057 Uiso calc R 1 . .
    C C4 1.1909(3) -0.16849(15) 0.58042(10) 0.0423(5) Uani d . 1 . .
    C C5 1.3154(3) -0.2041(2) 0.54033(13) 0.0600(7) Uani d . 1 . .
    H H5 1.3603 -0.2662 0.5489 0.072 Uiso calc R 1 . .
    C C6 1.3702(4) -0.1483(2) 0.48930(14) 0.0677(8) Uani d . 1 . .
    H H6 1.4518 -0.1728 0.4635 0.081 Uiso calc R 1 . .
    C C7 1.3040(3) -0.0549(2) 0.47599(11) 0.0546(6) Uani d . 1 . .
    H H7 1.3435 -0.0165 0.4419 0.065 Uiso calc R 1 . .
    C C8 1.1824(3) -0.01962(17) 0.51244(9) 0.0410(5) Uani d . 1 . .
    H H8 1.1381 0.0421 0.5021 0.049 Uiso calc R 1 . .
    C C9 1.1211(2) -0.07409(14) 0.56575(9) 0.0323(4) Uani d . 1 . .
    C C10 0.9960(2) -0.03785(14) 0.60657(8) 0.0298(4) Uani d . 1 . .
    C C11 0.9160(2) 0.05934(13) 0.59444(8) 0.0283(4) Uani d . 1 . .
    C C12 0.8330(2) 0.07958(14) 0.53500(8) 0.0309(4) Uani d . 1 . .
    C C13 0.8099(3) 0.00551(16) 0.48651(10) 0.0408(5) Uani d . 1 . .
    H H13 0.8506 -0.0584 0.4928 0.049 Uiso calc R 1 . .
    C C14 0.7289(3) 0.0268(2) 0.43082(10) 0.0518(6) Uani d . 1 . .
    H H14 0.7143 -0.0229 0.3997 0.062 Uiso calc R 1 . .
    C C15 0.6676(3) 0.1229(2) 0.42019(11) 0.0576(7) Uani d . 1 . .
    H H15 0.6153 0.1371 0.3815 0.069 Uiso calc R 1 . .
    C C16 0.6841(3) 0.19519(19) 0.46587(11) 0.0506(6) Uani d . 1 . .
    H H16 0.6415 0.2583 0.4585 0.061 Uiso calc R 1 . .
    C C17 0.7658(3) 0.17582(15) 0.52499(9) 0.0368(4) Uani d . 1 . .
    C C18 0.7767(3) 0.24789(15) 0.57516(10) 0.0432(5) Uani d . 1 . .
    H H18 0.7358 0.3116 0.5684 0.052 Uiso calc R 1 . .
    C C19 0.8456(2) 0.22598(15) 0.63296(10) 0.0368(4) Uani d . 1 . .
    H H19 0.8485 0.2734 0.6660 0.044 Uiso calc R 1 . .
    C C20 0.9126(2) 0.13082(14) 0.64237(8) 0.0291(4) Uani d . 1 . .
    C C21 0.4505(5) 0.0741(4) 0.64124(17) 0.1067(15) Uani d . 1 . .
    H H21A 0.5583 0.0913 0.6504 0.160 Uiso calc R 1 . .
    H H21B 0.3883 0.1340 0.6381 0.160 Uiso calc R 1 . .
    H H21C 0.4454 0.0383 0.6008 0.160 Uiso calc R 1 . .
    C C22 0.3853(4) 0.0076(3) 0.69635(16) 0.0853(10) Uani d . 1 . .
    H H22A 0.2711 0.0039 0.6928 0.102 Uiso calc R 1 . .
    H H22B 0.4271 -0.0597 0.6917 0.102 Uiso calc R 1 . .
    C C23 0.4903(4) -0.1247(2) 0.8033(2) 0.0832(10) Uani d . 1 . .
    H H23A 0.5959 -0.1078 0.7903 0.125 Uiso calc R 1 . .
    H H23B 0.4408 -0.1636 0.7698 0.125 Uiso calc R 1 . .
    H H23C 0.4936 -0.1629 0.8428 0.125 Uiso calc R 1 . .
    C C24 0.3995(4) -0.0330(2) 0.81405(17) 0.0715(8) Uani d . 1 . .
    H H24A 0.4278 -0.0052 0.8560 0.086 Uiso calc R 1 . .
    H H24B 0.2879 -0.0494 0.8152 0.086 Uiso calc R 1 . .
    C C25 0.4079(4) 0.1960(3) 0.83499(17) 0.0788(9) Uani d . 1 . .
    H H25A 0.5187 0.2078 0.8285 0.118 Uiso calc R 1 . .
    H H25B 0.3927 0.1586 0.8744 0.118 Uiso calc R 1 . .
    H H25C 0.3536 0.2589 0.8382 0.118 Uiso calc R 1 . .
    C C26 0.3437(3) 0.1379(3) 0.77885(19) 0.0791(9) Uani d . 1 . .
    H H26A 0.2352 0.1200 0.7887 0.095 Uiso calc R 1 . .
    H H26B 0.3415 0.1816 0.7412 0.095 Uiso calc R 1 . .
    N N1 0.4281(2) 0.04695(16) 0.76106(11) 0.0490(5) Uani d . 1 . .
    O O1 0.84192(17) -0.05577(10) 0.70278(6) 0.0372(3) Uani d . 1 . .
    O O2 0.98292(15) 0.11072(10) 0.70184(6) 0.0308(3) Uani d . 1 . .
    O O3 1.01033(17) 0.00302(13) 0.79917(7) 0.0491(4) Uani d . 1 . .
    O O4 0.74028(17) 0.08038(13) 0.77268(7) 0.0451(4) Uani d . 1 . .
    P P1 0.89188(6) 0.03523(4) 0.75172(2) 0.03329(13) Uani d . 1 . .
    H H1N 0.529(4) 0.0593(18) 0.7609(12) 0.044(7) Uiso d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 C10 . 1.378(3) ?
    C1 O1 . 1.385(2) ?
    C1 C2 . 1.401(3) ?
    C2 C3 . 1.363(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.414(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.419(3) ?
    C4 C9 . 1.425(3) ?
    C5 C6 . 1.368(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.396(4) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.358(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.415(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.435(3) ?
    C10 C11 . 1.485(3) ?
    C11 C20 . 1.373(2) ?
    C11 C12 . 1.436(2) ?
    C12 C13 . 1.418(3) ?
    C12 C17 . 1.421(3) ?
    C13 C14 . 1.365(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.402(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.355(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.422(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.414(3) ?
    C18 C19 . 1.356(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.405(3) ?
    C19 H19 . 0.9300 ?
    C20 O2 . 1.386(2) ?
    C21 C22 . 1.542(5) ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C22 N1 . 1.476(4) ?
    C22 H22A . 0.9700 ?
    C22 H22B . 0.9700 ?
    C23 C24 . 1.463(4) ?
    C23 H23A . 0.9600 ?
    C23 H23B . 0.9600 ?
    C23 H23C . 0.9600 ?
    C24 N1 . 1.545(4) ?
    C24 H24A . 0.9700 ?
    C24 H24B . 0.9700 ?
    C25 C26 . 1.494(4) ?
    C25 H25A . 0.9600 ?
    C25 H25B . 0.9600 ?
    C25 H25C . 0.9600 ?
    C26 N1 . 1.456(4) ?
    C26 H26A . 0.9700 ?
    C26 H26B . 0.9700 ?
    N1 H1N . 0.87(3) ?
    O1 P1 . 1.6340(14) ?
    O2 P1 . 1.6319(13) ?
    O3 P1 . 1.4636(15) ?
    O4 P1 . 1.4815(16) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C10 C1 O1 . . 119.10(18) ?
    C10 C1 C2 . . 122.5(2) ?
    O1 C1 C2 . . 118.39(18) ?
    C3 C2 C1 . . 119.8(2) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 120.50(19) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    C3 C4 C5 . . 121.3(2) ?
    C3 C4 C9 . . 119.9(2) ?
    C5 C4 C9 . . 118.8(2) ?
    C6 C5 C4 . . 121.0(2) ?
    C6 C5 H5 . . 119.5 ?
    C4 C5 H5 . . 119.5 ?
    C5 C6 C7 . . 120.1(2) ?
    C5 C6 H6 . . 120.0 ?
    C7 C6 H6 . . 120.0 ?
    C8 C7 C6 . . 120.4(3) ?
    C8 C7 H7 . . 119.8 ?
    C6 C7 H7 . . 119.8 ?
    C7 C8 C9 . . 121.8(2) ?
    C7 C8 H8 . . 119.1 ?
    C9 C8 H8 . . 119.1 ?
    C8 C9 C4 . . 117.86(19) ?
    C8 C9 C10 . . 123.39(17) ?
    C4 C9 C10 . . 118.73(18) ?
    C1 C10 C9 . . 118.40(17) ?
    C1 C10 C11 . . 119.26(17) ?
    C9 C10 C11 . . 122.20(16) ?
    C20 C11 C12 . . 118.06(16) ?
    C20 C11 C10 . . 119.80(15) ?
    C12 C11 C10 . . 122.05(16) ?
    C13 C12 C17 . . 118.33(17) ?
    C13 C12 C11 . . 122.32(17) ?
    C17 C12 C11 . . 119.31(17) ?
    C14 C13 C12 . . 120.9(2) ?
    C14 C13 H13 . . 119.5 ?
    C12 C13 H13 . . 119.5 ?
    C13 C14 C15 . . 120.5(2) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C16 C15 C14 . . 120.4(2) ?
    C16 C15 H15 . . 119.8 ?
    C14 C15 H15 . . 119.8 ?
    C15 C16 C17 . . 120.9(2) ?
    C15 C16 H16 . . 119.6 ?
    C17 C16 H16 . . 119.6 ?
    C18 C17 C12 . . 118.96(17) ?
    C18 C17 C16 . . 122.1(2) ?
    C12 C17 C16 . . 118.87(19) ?
    C19 C18 C17 . . 121.39(18) ?
    C19 C18 H18 . . 119.3 ?
    C17 C18 H18 . . 119.3 ?
    C18 C19 C20 . . 119.30(18) ?
    C18 C19 H19 . . 120.3 ?
    C20 C19 H19 . . 120.3 ?
    C11 C20 O2 . . 119.33(16) ?
    C11 C20 C19 . . 122.59(17) ?
    O2 C20 C19 . . 118.03(16) ?
    C22 C21 H21A . . 109.5 ?
    C22 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    C22 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    N1 C22 C21 . . 111.7(3) ?
    N1 C22 H22A . . 109.3 ?
    C21 C22 H22A . . 109.3 ?
    N1 C22 H22B . . 109.3 ?
    C21 C22 H22B . . 109.3 ?
    H22A C22 H22B . . 107.9 ?
    C24 C23 H23A . . 109.5 ?
    C24 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C24 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C23 C24 N1 . . 113.0(2) ?
    C23 C24 H24A . . 109.0 ?
    N1 C24 H24A . . 109.0 ?
    C23 C24 H24B . . 109.0 ?
    N1 C24 H24B . . 109.0 ?
    H24A C24 H24B . . 107.8 ?
    C26 C25 H25A . . 109.5 ?
    C26 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C26 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    N1 C26 C25 . . 116.7(3) ?
    N1 C26 H26A . . 108.1 ?
    C25 C26 H26A . . 108.1 ?
    N1 C26 H26B . . 108.1 ?
    C25 C26 H26B . . 108.1 ?
    H26A C26 H26B . . 107.3 ?
    C26 N1 C22 . . 113.8(3) ?
    C26 N1 C24 . . 108.8(2) ?
    C22 N1 C24 . . 110.6(2) ?
    C26 N1 H1N . . 108.9(16) ?
    C22 N1 H1N . . 107.8(17) ?
    C24 N1 H1N . . 106.7(16) ?
    C1 O1 P1 . . 117.46(12) ?
    C20 O2 P1 . . 118.16(11) ?
    O3 P1 O4 . . 121.23(9) ?
    O3 P1 O2 . . 106.13(8) ?
    O4 P1 O2 . . 109.87(9) ?
    O3 P1 O1 . . 111.67(9) ?
    O4 P1 O1 . . 104.96(8) ?
    O2 P1 O1 . . 101.22(7) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C10 C1 C2 C3 . . . . 1.5(3) ?
    O1 C1 C2 C3 . . . . 179.86(19) ?
    C1 C2 C3 C4 . . . . 1.8(3) ?
    C2 C3 C4 C5 . . . . 176.2(2) ?
    C2 C3 C4 C9 . . . . -1.5(3) ?
    C3 C4 C5 C6 . . . . -176.3(2) ?
    C9 C4 C5 C6 . . . . 1.4(4) ?
    C4 C5 C6 C7 . . . . 0.1(4) ?
    C5 C6 C7 C8 . . . . -1.6(4) ?
    C6 C7 C8 C9 . . . . 1.7(4) ?
    C7 C8 C9 C4 . . . . -0.2(3) ?
    C7 C8 C9 C10 . . . . 178.0(2) ?
    C3 C4 C9 C8 . . . . 176.4(2) ?
    C5 C4 C9 C8 . . . . -1.3(3) ?
    C3 C4 C9 C10 . . . . -1.9(3) ?
    C5 C4 C9 C10 . . . . -179.6(2) ?
    O1 C1 C10 C9 . . . . 176.82(16) ?
    C2 C1 C10 C9 . . . . -4.8(3) ?
    O1 C1 C10 C11 . . . . 1.1(3) ?
    C2 C1 C10 C11 . . . . 179.47(18) ?
    C8 C9 C10 C1 . . . . -173.24(18) ?
    C4 C9 C10 C1 . . . . 4.9(3) ?
    C8 C9 C10 C11 . . . . 2.3(3) ?
    C4 C9 C10 C11 . . . . -179.53(17) ?
    C1 C10 C11 C20 . . . . 52.0(3) ?
    C9 C10 C11 C20 . . . . -123.5(2) ?
    C1 C10 C11 C12 . . . . -124.3(2) ?
    C9 C10 C11 C12 . . . . 60.2(3) ?
    C20 C11 C12 C13 . . . . -170.67(19) ?
    C10 C11 C12 C13 . . . . 5.7(3) ?
    C20 C11 C12 C17 . . . . 6.8(3) ?
    C10 C11 C12 C17 . . . . -176.80(18) ?
    C17 C12 C13 C14 . . . . 1.7(3) ?
    C11 C12 C13 C14 . . . . 179.3(2) ?
    C12 C13 C14 C15 . . . . 0.5(4) ?
    C13 C14 C15 C16 . . . . -1.8(4) ?
    C14 C15 C16 C17 . . . . 1.0(4) ?
    C13 C12 C17 C18 . . . . 174.9(2) ?
    C11 C12 C17 C18 . . . . -2.7(3) ?
    C13 C12 C17 C16 . . . . -2.6(3) ?
    C11 C12 C17 C16 . . . . 179.8(2) ?
    C15 C16 C17 C18 . . . . -176.1(3) ?
    C15 C16 C17 C12 . . . . 1.3(4) ?
    C12 C17 C18 C19 . . . . -2.0(3) ?
    C16 C17 C18 C19 . . . . 175.4(2) ?
    C17 C18 C19 C20 . . . . 2.3(3) ?
    C12 C11 C20 O2 . . . . 175.82(16) ?
    C10 C11 C20 O2 . . . . -0.6(3) ?
    C12 C11 C20 C19 . . . . -6.7(3) ?
    C10 C11 C20 C19 . . . . 176.85(18) ?
    C18 C19 C20 C11 . . . . 2.2(3) ?
    C18 C19 C20 O2 . . . . 179.68(19) ?
    C25 C26 N1 C22 . . . . -165.1(3) ?
    C25 C26 N1 C24 . . . . 71.1(3) ?
    C21 C22 N1 C26 . . . . 71.5(4) ?
    C21 C22 N1 C24 . . . . -165.7(3) ?
    C23 C24 N1 C26 . . . . -175.3(3) ?
    C23 C24 N1 C22 . . . . 59.1(4) ?
    C10 C1 O1 P1 . . . . -76.8(2) ?
    C2 C1 O1 P1 . . . . 104.78(18) ?
    C11 C20 O2 P1 . . . . -74.93(19) ?
    C19 C20 O2 P1 . . . . 107.47(18) ?
    C20 O2 P1 O3 . . . . 162.56(13) ?
    C20 O2 P1 O4 . . . . -64.72(14) ?
    C20 O2 P1 O1 . . . . 45.86(14) ?
    C1 O1 P1 O3 . . . . -65.43(15) ?
    C1 O1 P1 O4 . . . . 161.44(14) ?
    C1 O1 P1 O2 . . . . 47.12(14) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1N O4 1_555 0.87(3) 1.83(3) 2.689(2) 172(2)
    C24 H24B O3 1_455 0.97 2.47 3.342(4) 149
    C26 H26A O3 1_455 0.97 2.47 3.373(3) 155
