#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:34:31 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178954 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/83/4118361.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_4118361
loop_
_publ_author_name
'Angélique Ferry'
'Xavier Guinchard'
'Pascal Retailleau'
'David Crich'
_publ_contact_author_address
;Centre de Recherches de Gif
Institut de Chimie des Substances Naturelles-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France
;
_publ_contact_author_email       xavier.guinchard@icsn.cnrs-gif.fr
_publ_contact_author_fax         +33169077247
_publ_contact_author_name        'Guinchard, Xavier'
_publ_contact_author_phone       +33169823011
_publ_section_title
;
 Synthesis, Characterization, and Coupling Reactions of Six-Membered
 Cyclic P-Chiral Ammonium Phosphonite-Boranes; Reactive H-Phosphinate
 Equivalents for the Stereoselective Synthesis of Glycomimetics
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12289
_journal_page_last               12301
_journal_paper_doi               10.1021/ja305104b
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C24 H29 O9 P'
_chemical_formula_sum            'C24 H29 O9 P'
_chemical_formula_weight         492.44
_chemical_name_systematic
; 
((2R,3R,4S,5S,6R)-3-acetoxy-4,5-bis(benzyloxy)-2-methoxy-2-oxido-
1,2-oxaphosphinan-6yl)methyl acetate 
;
_space_group_IT_number           154
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   10.583(7)
_cell_length_b                   10.583(7)
_cell_length_c                   39.571(6)
_cell_measurement_temperature    293(2)
_cell_volume                     3838(4)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_type
'RAPID II large area curved imaging plate detector '
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 36
               Slice: 20.0000 - 200.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 270.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 33
               Slice: 20.0000 - 185.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 33
               Slice: 20.0000 - 185.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: 0.0000
scan:
    Number of images: 32
               Slice: 20.0000 - 184.0000
         Image width: 5.0000
            Exp time: 180.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: 0.0000

;
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.097445
_diffrn_orient_matrix_UB_12      0.007377
_diffrn_orient_matrix_UB_13      -0.001052
_diffrn_orient_matrix_UB_21      -0.027148
_diffrn_orient_matrix_UB_22      -0.068410
_diffrn_orient_matrix_UB_23      0.019651
_diffrn_orient_matrix_UB_31      -0.039528
_diffrn_orient_matrix_UB_32      -0.084029
_diffrn_orient_matrix_UB_33      -0.016091
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            16978
_diffrn_reflns_theta_full        50.00
_diffrn_reflns_theta_max         50.00
_diffrn_reflns_theta_min         6.58
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       cube
_exptl_crystal_F_000             1422
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881;1051 Bijvoet pairs'
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_coef       0.0065(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0838
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1350P)²+2.0279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2348
_reflns_number_gt                2045
_reflns_number_total             2639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja305104b_si_002_4.cif
_cod_data_source_block           8m\a
_cod_database_code               4118361
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -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
P1 P 0.5831(3) 0.1090(3) 0.36877(6) 0.1010(9) Uani 1 1 d . . .
O1 O 0.6023(7) -0.0216(7) 0.38020(14) 0.1135(19) Uani 1 1 d . . .
O2 O 0.6609(7) 0.1867(7) 0.33866(14) 0.1140(19) Uani 1 1 d . . .
O3 O 0.4156(7) 0.0485(8) 0.36372(13) 0.120(2) Uani 1 1 d . B .
O6 O 0.2587(6) -0.0402(7) 0.44892(15) 0.1086(19) Uani 1 1 d . . .
O7 O 0.5240(7) 0.2050(7) 0.46394(14) 0.1056(18) Uani 1 1 d . . .
O8 O 0.6076(7) 0.3348(8) 0.40015(15) 0.1095(18) Uani 1 1 d . . .
O9 O 0.8284(12) 0.4795(10) 0.4169(3) 0.211(5) Uani 1 1 d . . .
C23 C 0.6974(15) 0.5875(13) 0.3954(3) 0.160(5) Uani 1 1 d . . .
H23A H 0.7302 0.6590 0.4131 0.240 Uiso 1 1 calc R . .
H23B H 0.5954 0.5506 0.3913 0.240 Uiso 1 1 calc R . .
H23C H 0.7515 0.6318 0.3751 0.240 Uiso 1 1 calc R . .
C1 C 0.6166(9) 0.2038(10) 0.40731(19) 0.094(2) Uani 1 1 d . . .
H1 H 0.7152 0.2324 0.4152 0.113 Uiso 1 1 calc R . .
C2 C 0.5069(10) 0.1205(10) 0.4354(2) 0.094(2) Uani 1 1 d . . .
H2 H 0.5201 0.0389 0.4423 0.113 Uiso 1 1 calc R . .
C3 C 0.3524(10) 0.0592(10) 0.4239(2) 0.099(2) Uani 1 1 d . B .
H3 H 0.3300 0.1377 0.4204 0.119 Uiso 1 1 calc R . .
C4 C 0.3159(10) -0.0373(12) 0.3914(2) 0.128(4) Uani 1 1 d D . .
H41 H 0.3130 -0.1301 0.3954 0.154 Uiso 0.50 1 calc PR A 1
H42 H 0.3592 -0.0969 0.3977 0.154 Uiso 0.50 1 calc PR A 2
C8 C 0.1802(12) 0.0109(11) 0.4678(3) 0.125(3) Uani 1 1 d . . .
H8A H 0.1228 0.0349 0.4528 0.150 Uiso 1 1 calc R . .
H8B H 0.2472 0.0983 0.4801 0.150 Uiso 1 1 calc R . .
C9 C 0.0798(13) -0.1092(11) 0.4925(3) 0.103(3) Uani 1 1 d . . .
C10 C 0.1047(15) -0.0977(13) 0.5258(3) 0.126(3) Uani 1 1 d . . .
H10 H 0.1887 -0.0170 0.5339 0.151 Uiso 1 1 calc R . .
C11 C 0.011(2) -0.200(2) 0.5484(3) 0.136(4) Uani 1 1 d . . .
H11 H 0.0302 -0.1897 0.5715 0.163 Uiso 1 1 calc R . .
C12 C -0.109(2) -0.317(2) 0.5361(5) 0.144(5) Uani 1 1 d . . .
H12 H -0.1766 -0.3850 0.5509 0.173 Uiso 1 1 calc R . .
C13 C -0.1332(14) -0.3361(15) 0.5014(5) 0.146(4) Uani 1 1 d . . .
H13 H -0.2131 -0.4202 0.4930 0.175 Uiso 1 1 calc R . .
C14 C -0.0389(14) -0.2311(15) 0.4801(3) 0.122(3) Uani 1 1 d . . .
H14 H -0.0551 -0.2422 0.4569 0.146 Uiso 1 1 calc R . .
C15 C 0.6047(14) 0.1959(14) 0.4917(2) 0.146(4) Uani 1 1 d . . .
H15A H 0.7081 0.2597 0.4876 0.175 Uiso 1 1 calc R . .
H15B H 0.5865 0.0969 0.4936 0.175 Uiso 1 1 calc R . .
C16 C 0.5637(11) 0.2383(11) 0.5236(2) 0.108(3) Uani 1 1 d . . .
C17 C 0.4945(14) 0.3235(12) 0.5242(3) 0.141(4) Uani 1 1 d . . .
H17 H 0.4747 0.3552 0.5040 0.169 Uiso 1 1 calc R . .
C18 C 0.4565(13) 0.3598(14) 0.5543(3) 0.149(4) Uani 1 1 d . . .
H18 H 0.4074 0.4122 0.5544 0.179 Uiso 1 1 calc R . .
C19 C 0.4913(19) 0.3183(16) 0.5846(3) 0.171(6) Uani 1 1 d . . .
H19 H 0.4705 0.3471 0.6050 0.205 Uiso 1 1 calc R . .
C20 C 0.556(2) 0.235(2) 0.5840(3) 0.212(8) Uani 1 1 d . . .
H20 H 0.5709 0.2001 0.6043 0.254 Uiso 1 1 calc R . .
C21 C 0.5996(15) 0.2029(14) 0.5545(3) 0.154(4) Uani 1 1 d . . .
H21 H 0.6544 0.1563 0.5550 0.184 Uiso 1 1 calc R . .
C22 C 0.7213(17) 0.4627(16) 0.4059(3) 0.137(4) Uani 1 1 d . . .
C24 C 0.5796(13) -0.1388(12) 0.3563(2) 0.135(4) Uani 1 1 d . . .
H24A H 0.5948 -0.2100 0.3678 0.203 Uiso 1 1 calc R . .
H24B H 0.6476 -0.0977 0.3379 0.203 Uiso 1 1 calc R . .
H24C H 0.4818 -0.1846 0.3476 0.203 Uiso 1 1 calc R . .
C5 C 0.1666(14) -0.0573(16) 0.3783(4) 0.092(5) Uani 0.50 1 d PDU B 1
H5A H 0.1482 -0.1003 0.3560 0.110 Uiso 0.50 1 calc PR B 1
H5B H 0.0896 -0.1262 0.3931 0.110 Uiso 0.50 1 calc PR B 1
O4 O 0.1578(10) 0.0737(11) 0.3767(3) 0.094(3) Uani 0.50 1 d PD B 1
C6 C 0.034(2) 0.0554(15) 0.3708(5) 0.121(6) Uani 0.50 1 d PD B 1
C7 C 0.029(2) 0.194(2) 0.3651(7) 0.182(12) Uani 0.50 1 d PD B 1
H7A H 0.1218 0.2768 0.3703 0.273 Uiso 0.50 1 calc PR B 1
H7B H -0.0447 0.1936 0.3794 0.273 Uiso 0.50 1 calc PR B 1
H7C H 0.0049 0.1987 0.3419 0.273 Uiso 0.50 1 calc PR B 1
O5 O -0.0763(14) -0.0663(18) 0.3670(5) 0.174(7) Uani 0.50 1 d PD B 1
C25 C 0.1639(19) -0.161(2) 0.3780(7) 0.172(8) Uani 0.50 1 d PDU B 2
H25A H 0.1011 -0.2029 0.3975 0.206 Uiso 0.50 1 calc PR B 2
H25B H 0.1224 -0.1137 0.3646 0.206 Uiso 0.50 1 calc PR B 2
O24 O 0.1541(17) -0.2793(19) 0.3583(4) 0.196(6) Uani 0.50 1 d PDU B 2
C26 C 0.029(3) -0.372(3) 0.3493(7) 0.234(10) Uani 0.50 1 d PDU . 2
C27 C -0.085(3) -0.326(3) 0.3534(8) 0.217(10) Uani 0.50 1 d PDU C 2
H27A H -0.0679 -0.2731 0.3741 0.325 Uiso 0.50 1 calc PR C 2
H27B H -0.1805 -0.4117 0.3540 0.325 Uiso 0.50 1 calc PR C 2
H27C H -0.0792 -0.2658 0.3348 0.325 Uiso 0.50 1 calc PR C 2
O25 O 0.0000 -0.4846(18) 0.3333 0.295(9) Uani 1 2 d SDU . 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O2 P1 O1 116.9(4) . .
O2 P1 O3 109.5(3) . .
O1 P1 O3 107.2(4) . .
O2 P1 C1 119.6(4) . .
O1 P1 C1 100.1(4) . .
O3 P1 C1 102.0(4) . .
C24 O1 P1 121.2(5) . .
C4 O3 P1 118.2(5) . .
C8 O6 C3 114.2(7) . .
C2 O7 C15 118.1(6) . .
C22 O8 C1 119.0(8) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O8 C1 C2 107.2(6) . .
O8 C1 P1 106.4(5) . .
C2 C1 P1 114.9(6) . .
O8 C1 H1 109.4 . .
C2 C1 H1 109.4 . .
P1 C1 H1 109.4 . .
O7 C2 C3 106.6(6) . .
O7 C2 C1 113.7(7) . .
C3 C2 C1 112.4(6) . .
O7 C2 H2 108.0 . .
C3 C2 H2 108.0 . .
C1 C2 H2 108.0 . .
O6 C3 C2 108.5(6) . .
O6 C3 C4 103.6(7) . .
C2 C3 C4 113.0(7) . .
O6 C3 H3 110.5 . .
C2 C3 H3 110.5 . .
C4 C3 H3 110.5 . .
O3 C4 C3 109.9(8) . .
O3 C4 C25 112.5(13) . .
C3 C4 C25 129.3(13) . .
O3 C4 C5 101.6(9) . .
C3 C4 C5 105.1(10) . .
C25 C4 C5 40.2(11) . .
O3 C4 H41 113.1 . .
C3 C4 H41 113.1 . .
C25 C4 H41 73.5 . .
C5 C4 H41 113.1 . .
O3 C4 H42 99.5 . .
C3 C4 H42 99.5 . .
C25 C4 H42 99.5 . .
C5 C4 H42 139.4 . .
H41 C4 H42 26.3 . .
O6 C8 C9 108.4(7) . .
O6 C8 H8A 110.0 . .
C9 C8 H8A 110.0 . .
O6 C8 H8B 110.0 . .
C9 C8 H8B 110.0 . .
H8A C8 H8B 108.4 . .
C10 C9 C14 119.0(10) . .
C10 C9 C8 122.0(12) . .
C14 C9 C8 119.0(11) . .
C9 C10 C11 122.6(13) . .
C9 C10 H10 118.7 . .
C11 C10 H10 118.7 . .
C12 C11 C10 117.7(13) . .
C12 C11 H11 121.2 . .
C10 C11 H11 121.2 . .
C11 C12 C13 121.0(13) . .
C11 C12 H12 119.5 . .
C13 C12 H12 119.5 . .
C14 C13 C12 119.0(14) . .
C14 C13 H13 120.5 . .
C12 C13 H13 120.5 . .
C13 C14 C9 120.4(12) . .
C13 C14 H14 119.8 . .
C9 C14 H14 119.8 . .
O7 C15 C16 111.2(8) . .
O7 C15 H15A 109.4 . .
C16 C15 H15A 109.4 . .
O7 C15 H15B 109.4 . .
C16 C15 H15B 109.4 . .
H15A C15 H15B 108.0 . .
C21 C16 C17 117.1(10) . .
C21 C16 C15 120.7(9) . .
C17 C16 C15 122.1(9) . .
C18 C17 C16 120.6(11) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C17 C18 C19 120.0(11) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C20 C19 C18 119.5(11) . .
C20 C19 H19 120.3 . .
C18 C19 H19 120.3 . .
C19 C20 C21 121.4(13) . .
C19 C20 H20 119.3 . .
C21 C20 H20 119.3 . .
C20 C21 C16 121.0(12) . .
C20 C21 H21 119.5 . .
C16 C21 H21 119.5 . .
O9 C22 O8 123.8(12) . .
O9 C22 C23 123.5(14) . .
O8 C22 C23 112.7(12) . .
O1 C24 H24A 109.5 . .
O1 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
O1 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
O4 C5 C4 115.5(12) . .
O4 C5 H5A 108.4 . .
C4 C5 H5A 108.4 . .
O4 C5 H5B 108.4 . .
C4 C5 H5B 108.4 . .
H5A C5 H5B 107.5 . .
C6 O4 C5 115.4(9) . .
O4 C6 O5 123.8(14) . .
O4 C6 C7 115.2(12) . .
O5 C6 C7 120.8(19) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O24 C25 C4 120.3(17) . .
O24 C25 H25A 107.2 . .
C4 C25 H25A 107.2 . .
O24 C25 H25B 107.2 . .
C4 C25 H25B 107.2 . .
H25A C25 H25B 106.9 . .
C26 O24 C25 115.3(9) . .
O24 C26 O25 123.6(14) . .
O24 C26 C26 128(3) . 5
O25 C26 C26 56.7(14) . 5
O24 C26 C27 115.0(12) . .
O25 C26 C27 121(2) . .
C26 C26 C27 80.5(18) 5 .
O24 C26 C27 79(2) . 5
O25 C26 C27 99.0(19) . 5
C26 C26 C27 53.2(14) 5 5
C27 C26 C27 82(2) . 5
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C26 O25 C26 67(3) 5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.448(6) .
P1 O1 1.562(7) .
P1 O3 1.567(6) .
P1 C1 1.761(8) .
O1 C24 1.482(10) .
O3 C4 1.475(11) .
O6 C8 1.411(10) .
O6 C3 1.424(10) .
O7 C2 1.396(9) .
O7 C15 1.422(10) .
O8 C22 1.304(14) .
O8 C1 1.464(10) .
O9 C22 1.143(13) .
C23 C22 1.522(16) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C1 C2 1.527(11) .
C1 H1 0.9800 .
C2 C3 1.496(12) .
C2 H2 0.9800 .
C3 C4 1.568(13) .
C3 H3 0.9800 .
C4 C25 1.572(15) .
C4 C5 1.572(14) .
C4 H41 0.9800 .
C4 H42 0.9800 .
C8 C9 1.533(13) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.337(13) .
C9 C14 1.364(14) .
C10 C11 1.375(17) .
C10 H10 0.9300 .
C11 C12 1.341(17) .
C11 H11 0.9300 .
C12 C13 1.393(17) .
C12 H12 0.9300 .
C13 C14 1.353(16) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.476(12) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C21 1.386(13) .
C16 C17 1.418(13) .
C17 C18 1.372(14) .
C17 H17 0.9300 .
C18 C19 1.388(16) .
C18 H18 0.9300 .
C19 C20 1.355(18) .
C19 H19 0.9300 .
C20 C21 1.364(16) .
C20 H20 0.9300 .
C21 H21 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C5 O4 1.437(15) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
O4 C6 1.24(2) .
C6 O5 1.243(16) .
C6 C7 1.51(2) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C25 O24 1.438(15) .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
O24 C26 1.24(2) .
C26 O25 1.244(16) .
C26 C26 1.37(5) 5
C26 C27 1.51(2) .
C26 C27 1.86(4) 5
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
O25 C26 1.244(16) 5
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O2 P1 O1 C24 -51.4(9) . .
O3 P1 O1 C24 71.9(8) . .
C1 P1 O1 C24 178.0(7) . .
O2 P1 O3 C4 178.7(7) . .
O1 P1 O3 C4 51.0(8) . .
C1 P1 O3 C4 -53.6(8) . .
C22 O8 C1 C2 116.3(10) . .
C22 O8 C1 P1 -120.2(8) . .
O2 P1 C1 O8 49.0(7) . .
O1 P1 C1 O8 177.9(5) . .
O3 P1 C1 O8 -71.9(6) . .
O2 P1 C1 C2 167.5(5) . .
O1 P1 C1 C2 -63.6(6) . .
O3 P1 C1 C2 46.6(6) . .
C15 O7 C2 C3 138.4(9) . .
C15 O7 C2 C1 -97.2(9) . .
O8 C1 C2 O7 -53.6(8) . .
P1 C1 C2 O7 -171.6(5) . .
O8 C1 C2 C3 67.6(9) . .
P1 C1 C2 C3 -50.4(8) . .
C8 O6 C3 C2 108.2(8) . .
C8 O6 C3 C4 -131.5(8) . .
O7 C2 C3 O6 -66.6(8) . .
C1 C2 C3 O6 168.2(7) . .
O7 C2 C3 C4 179.1(7) . .
C1 C2 C3 C4 53.9(10) . .
P1 O3 C4 C3 61.8(10) . .
P1 O3 C4 C25 -146.7(12) . .
P1 O3 C4 C5 172.7(8) . .
O6 C3 C4 O3 -174.6(7) . .
C2 C3 C4 O3 -57.4(11) . .
O6 C3 C4 C25 40.1(19) . .
C2 C3 C4 C25 157.3(16) . .
O6 C3 C4 C5 76.8(10) . .
C2 C3 C4 C5 -166.1(9) . .
C3 O6 C8 C9 177.6(9) . .
O6 C8 C9 C10 109.0(10) . .
O6 C8 C9 C14 -71.3(11) . .
C14 C9 C10 C11 -3.7(15) . .
C8 C9 C10 C11 176.1(9) . .
C9 C10 C11 C12 0.6(16) . .
C10 C11 C12 C13 3.4(18) . .
C11 C12 C13 C14 -4.4(18) . .
C12 C13 C14 C9 1.2(16) . .
C10 C9 C14 C13 2.7(15) . .
C8 C9 C14 C13 -177.1(9) . .
C2 O7 C15 C16 -156.4(9) . .
O7 C15 C16 C21 163.5(10) . .
O7 C15 C16 C17 -20.4(16) . .
C21 C16 C17 C18 -4.4(17) . .
C15 C16 C17 C18 179.3(11) . .
C16 C17 C18 C19 3(2) . .
C17 C18 C19 C20 -3(2) . .
C18 C19 C20 C21 6(3) . .
C19 C20 C21 C16 -8(3) . .
C17 C16 C21 C20 7(2) . .
C15 C16 C21 C20 -176.8(14) . .
C1 O8 C22 O9 -1.7(19) . .
C1 O8 C22 C23 176.9(8) . .
O3 C4 C5 O4 -67.2(14) . .
C3 C4 C5 O4 47.4(15) . .
C25 C4 C5 O4 -178(3) . .
C4 C5 O4 C6 -170.8(13) . .
C5 O4 C6 O5 1(3) . .
C5 O4 C6 C7 -173.2(17) . .
O3 C4 C25 O24 65(3) . .
C3 C4 C25 O24 -150.7(19) . .
C5 C4 C25 O24 146(4) . .
C4 C25 O24 C26 179(2) . .
C25 O24 C26 O25 -177(2) . .
C25 O24 C26 C26 112(2) . 5
C25 O24 C26 C27 14(3) . .
C25 O24 C26 C27 89(2) . 5
O24 C26 O25 C26 -117(4) . 5
C27 C26 O25 C26 52(2) . 5
C27 C26 O25 C26 -33.9(14) 5 5
