# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009


data_global

_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'G Blackburn'
_publ_contact_author_email       G.M.BLACKBURN@SHEFFIELD.AC.UK

_publ_section_title              
;
Chirality at Phosphorus in Pentacoordinate
Spirophosphoranes: Stereochemistry by X-ray Structure and
Spectroscopic Analysis
;

#==============================================================================

_publ_contact_author             'Y. F. Zhao'
loop_
_publ_author_name
'G Blackburn'
'Jian-Nan Guo'
'Jian-Bo Hou'
'Yan Liu'
'Peng-Xiang Xu'
'Hui Zhang'
'Yu-Fen Zhao'

# Attachment 'CCDC-721774(3b)-090609.cif'

data_212121
_database_code_depnum_ccdc_archive 'CCDC 721774'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(3S, 5\L, 8S)-3,8-Dibenzyl-1,6-dioxa-4,9-diaza-5\L5-phosphaspiro
[4.4]-nonane-2,7-dione
;
_chemical_name_common            
;
(3S, 5clambda, 8S)-3,8-Dibenzyl-1,6-dioxa-4,9-diaza-5clambda5-
phosphaspiro (4.4)-nonane-2,7-dione
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N2 O4 P'
_chemical_formula_sum            'C18 H19 N2 O4 P'
_chemical_formula_weight         358.32

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_chemical_absolute_configuration syn

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                   6.0491(4)
_cell_length_b                   8.3323(5)
_cell_length_c                   34.349(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1731.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1823
_cell_measurement_theta_min      2.9541
_cell_measurement_theta_max      32.7613

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9366
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   'CrysAlis RED; (Oxford Diffraction, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Gemini S Ultra CCD Area Detector'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6300
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0912
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2821
_reflns_number_gt                1819
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(12)
_refine_ls_number_reflns         2821
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.892
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
O1 O 0.8531(3) 0.6489(2) 0.95283(5) 0.0267(5) Uani 1 1 d . . .
C2 C 0.8592(5) 0.4986(4) 0.96472(8) 0.0271(7) Uani 1 1 d . . .
O2 O 1.0342(3) 0.4254(2) 0.96788(5) 0.0333(5) Uani 1 1 d . . .
C3 C 0.6352(4) 0.4310(3) 0.97349(8) 0.0263(7) Uani 1 1 d . . .
H3A H 0.6265 0.4089 1.0015 0.032 Uiso 1 1 calc R . .
N4 N 0.4861(3) 0.5626(3) 0.96448(6) 0.0273(6) Uani 1 1 d . . .
H4A H 0.3452 0.5494 0.9657 0.033 Uiso 1 1 calc R . .
P5 P 0.58930(11) 0.73452(9) 0.95218(2) 0.0280(2) Uani 1 1 d . . .
H5 H 0.636(4) 0.837(3) 0.9818(7) 0.033(7) Uiso 1 1 d . . .
O6 O 0.3247(3) 0.8173(2) 0.95162(6) 0.0320(5) Uani 1 1 d . . .
O7 O 0.0869(4) 0.9465(2) 0.91325(7) 0.0536(7) Uani 1 1 d . . .
C7 C 0.2657(5) 0.8858(4) 0.91864(11) 0.0364(9) Uani 1 1 d . . .
C8 C 0.4481(5) 0.8812(4) 0.88837(9) 0.0318(7) Uani 1 1 d . . .
H8A H 0.4946 0.9912 0.8824 0.038 Uiso 1 1 calc R . .
N9 N 0.6276(4) 0.7979(3) 0.90764(6) 0.0298(6) Uani 1 1 d . . .
H9A H 0.7514 0.7822 0.8959 0.036 Uiso 1 1 calc R . .
C10 C 0.5874(4) 0.2757(3) 0.95148(8) 0.0320(7) Uani 1 1 d . . .
H10A H 0.6917 0.1946 0.9600 0.038 Uiso 1 1 calc R . .
H10B H 0.4405 0.2390 0.9585 0.038 Uiso 1 1 calc R . .
C11 C 0.6006(5) 0.2893(3) 0.90775(8) 0.0270(7) Uani 1 1 d . . .
C12 C 0.7923(5) 0.2469(4) 0.88847(9) 0.0360(8) Uani 1 1 d . . .
H12A H 0.9159 0.2152 0.9026 0.043 Uiso 1 1 calc R . .
C13 C 0.8013(5) 0.2515(4) 0.84798(10) 0.0463(9) Uani 1 1 d . . .
H13A H 0.9308 0.2221 0.8352 0.056 Uiso 1 1 calc R . .
C14 C 0.6220(6) 0.2989(3) 0.82684(9) 0.0447(9) Uani 1 1 d . . .
H14A H 0.6285 0.3007 0.7998 0.054 Uiso 1 1 calc R . .
C15 C 0.4316(5) 0.3439(4) 0.84573(9) 0.0411(8) Uani 1 1 d . . .
H15A H 0.3102 0.3783 0.8314 0.049 Uiso 1 1 calc R . .
C16 C 0.4187(5) 0.3386(3) 0.88580(9) 0.0340(8) Uani 1 1 d . . .
H16A H 0.2883 0.3680 0.8982 0.041 Uiso 1 1 calc R . .
C17 C 0.3686(5) 0.8005(4) 0.85108(8) 0.0372(8) Uani 1 1 d . . .
H17A H 0.3425 0.6876 0.8563 0.045 Uiso 1 1 calc R . .
H17B H 0.2290 0.8480 0.8433 0.045 Uiso 1 1 calc R . .
C18 C 0.5313(5) 0.8154(4) 0.81775(9) 0.0400(8) Uani 1 1 d . . .
C19 C 0.7188(5) 0.7210(4) 0.81588(10) 0.0497(9) Uani 1 1 d . . .
H19A H 0.7429 0.6424 0.8346 0.060 Uiso 1 1 calc R . .
C20 C 0.8717(6) 0.7428(5) 0.78614(11) 0.0628(10) Uani 1 1 d . . .
H20A H 0.9978 0.6789 0.7853 0.075 Uiso 1 1 calc R . .
C21 C 0.8386(7) 0.8577(5) 0.75797(11) 0.0661(11) Uani 1 1 d . . .
H21A H 0.9411 0.8722 0.7381 0.079 Uiso 1 1 calc R . .
C22 C 0.6519(7) 0.9501(5) 0.75977(11) 0.0595(10) Uani 1 1 d . . .
H22A H 0.6274 1.0278 0.7408 0.071 Uiso 1 1 calc R . .
C23 C 0.5001(5) 0.9302(5) 0.78912(9) 0.0491(9) Uani 1 1 d . . .
H23A H 0.3747 0.9946 0.7898 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0182(10) 0.0315(11) 0.0306(11) 0.0026(11) -0.0029(10) -0.0011(8)
C2 0.0257(19) 0.0322(16) 0.0234(16) 0.0001(16) -0.0046(14) -0.0008(16)
O2 0.0242(12) 0.0376(11) 0.0381(12) 0.0057(11) -0.0033(9) 0.0016(10)
C3 0.0212(17) 0.0324(15) 0.0254(16) 0.0097(15) -0.0012(13) 0.0020(14)
N4 0.0189(13) 0.0263(13) 0.0368(15) 0.0022(13) 0.0031(11) 0.0010(10)
P5 0.0215(4) 0.0315(4) 0.0310(4) -0.0026(4) -0.0012(4) 0.0000(4)
O6 0.0201(11) 0.0319(11) 0.0439(12) -0.0014(13) -0.0001(10) 0.0058(8)
O7 0.0265(13) 0.0409(13) 0.0935(19) 0.0243(14) 0.0002(13) 0.0107(12)
C7 0.026(2) 0.0230(18) 0.060(3) 0.004(2) -0.0039(18) -0.0020(15)
C8 0.0264(18) 0.0283(18) 0.0408(18) 0.0083(16) -0.0071(16) -0.0021(14)
N9 0.0193(13) 0.0365(14) 0.0337(14) 0.0054(13) 0.0030(11) 0.0015(12)
C10 0.0229(15) 0.0322(16) 0.0407(17) 0.012(2) -0.0028(15) 0.0003(14)
C11 0.0249(17) 0.0208(14) 0.0353(17) 0.0006(14) 0.0013(15) -0.0035(14)
C12 0.0324(19) 0.0298(18) 0.046(2) -0.002(2) -0.0022(15) -0.0026(16)
C13 0.036(2) 0.048(2) 0.054(2) -0.009(2) 0.0102(17) 0.0016(18)
C14 0.057(2) 0.043(2) 0.0341(18) -0.0041(18) 0.0020(19) -0.0032(19)
C15 0.044(2) 0.0411(18) 0.038(2) -0.0069(18) -0.0147(18) 0.0041(17)
C16 0.030(2) 0.0289(16) 0.043(2) -0.0038(16) -0.0043(16) -0.0016(15)
C17 0.0267(18) 0.0344(18) 0.050(2) 0.0052(17) -0.0147(15) -0.0037(15)
C18 0.047(2) 0.0382(19) 0.0345(19) -0.0016(17) -0.0139(17) -0.0093(16)
C19 0.056(2) 0.041(2) 0.052(2) -0.003(2) -0.0109(19) 0.0042(19)
C20 0.054(2) 0.072(3) 0.062(2) -0.023(3) -0.007(2) 0.005(3)
C21 0.080(3) 0.076(3) 0.042(2) -0.009(3) 0.000(2) -0.015(3)
C22 0.082(3) 0.062(2) 0.035(2) -0.001(2) -0.010(2) -0.007(2)
C23 0.057(3) 0.053(2) 0.037(2) -0.003(2) -0.009(2) -0.0012(18)

_geom_special_details            
;
CgA is the centroid of the C18-C23 phenyl ring. 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.317(3) . ?
O1 P5 1.7483(18) . ?
C2 O2 1.226(3) . ?
C2 C3 1.498(4) . ?
C3 N4 1.453(3) . ?
C3 C10 1.526(4) . ?
C3 H3A 0.9800 . ?
N4 P5 1.619(2) . ?
N4 H4A 0.8600 . ?
P5 N9 1.635(2) . ?
P5 O6 1.7434(19) . ?
P5 H5 1.36(3) . ?
O6 C7 1.318(4) . ?
O7 C7 1.208(3) . ?
C7 C8 1.517(4) . ?
C8 N9 1.449(3) . ?
C8 C17 1.525(4) . ?
C8 H8A 0.9800 . ?
N9 H9A 0.8600 . ?
C10 C11 1.508(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.381(4) . ?
C11 C16 1.396(4) . ?
C12 C13 1.392(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.515(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.382(4) . ?
C18 C23 1.384(4) . ?
C19 C20 1.390(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.376(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.369(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.374(4) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

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
_geom_angle_publ_flag
C2 O1 P5 114.67(18) . . ?
O2 C2 O1 121.6(3) . . ?
O2 C2 C3 125.1(3) . . ?
O1 C2 C3 113.2(2) . . ?
N4 C3 C2 103.6(2) . . ?
N4 C3 C10 114.6(2) . . ?
C2 C3 C10 113.0(2) . . ?
N4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C10 C3 H3A 108.5 . . ?
C3 N4 P5 118.93(17) . . ?
C3 N4 H4A 120.5 . . ?
P5 N4 H4A 120.5 . . ?
N4 P5 N9 125.79(13) . . ?
N4 P5 O6 89.94(10) . . ?
N9 P5 O6 89.54(11) . . ?
N4 P5 O1 89.29(10) . . ?
N9 P5 O1 90.82(10) . . ?
O6 P5 O1 179.22(10) . . ?
N4 P5 H5 116.2(10) . . ?
N9 P5 H5 117.9(10) . . ?
O6 P5 H5 87.2(9) . . ?
O1 P5 H5 93.3(10) . . ?
C7 O6 P5 115.4(2) . . ?
O7 C7 O6 123.8(3) . . ?
O7 C7 C8 123.8(3) . . ?
O6 C7 C8 112.4(3) . . ?
N9 C8 C7 104.1(2) . . ?
N9 C8 C17 114.1(2) . . ?
C7 C8 C17 110.9(2) . . ?
N9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C17 C8 H8A 109.2 . . ?
C8 N9 P5 118.43(18) . . ?
C8 N9 H9A 120.8 . . ?
P5 N9 H9A 120.8 . . ?
C11 C10 C3 114.8(2) . . ?
C11 C10 H10A 108.6 . . ?
C3 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C3 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C10 120.2(3) . . ?
C16 C11 C10 121.2(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C15 C16 C11 120.2(3) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
C18 C17 C8 113.2(2) . . ?
C18 C17 H17A 108.9 . . ?
C8 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C8 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C23 118.2(3) . . ?
C19 C18 C17 121.4(3) . . ?
C23 C18 C17 120.3(3) . . ?
C18 C19 C20 120.4(4) . . ?
C18 C19 H19A 119.8 . . ?
C20 C19 H19A 119.8 . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C22 C21 C20 118.7(4) . . ?
C22 C21 H21A 120.7 . . ?
C20 C21 H21A 120.7 . . ?
C21 C22 C23 121.1(4) . . ?
C21 C22 H22A 119.4 . . ?
C23 C22 H22A 119.4 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23A 119.5 . . ?
C18 C23 H23A 119.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P5 O1 C2 O2 -177.5(2) . . . . ?
P5 O1 C2 C3 2.6(3) . . . . ?
O2 C2 C3 N4 -178.9(3) . . . . ?
O1 C2 C3 N4 1.0(3) . . . . ?
O2 C2 C3 C10 -54.3(4) . . . . ?
O1 C2 C3 C10 125.6(2) . . . . ?
C2 C3 N4 P5 -4.7(3) . . . . ?
C10 C3 N4 P5 -128.2(2) . . . . ?
C3 N4 P5 N9 95.8(2) . . . . ?
C3 N4 P5 O6 -174.8(2) . . . . ?
C3 N4 P5 O1 5.3(2) . . . . ?
C2 O1 P5 N4 -4.5(2) . . . . ?
C2 O1 P5 N9 -130.25(18) . . . . ?
C2 O1 P5 O6 -12(8) . . . . ?
N4 P5 O6 C7 -123.9(2) . . . . ?
N9 P5 O6 C7 1.9(2) . . . . ?
O1 P5 O6 C7 -116(8) . . . . ?
P5 O6 C7 O7 178.8(2) . . . . ?
P5 O6 C7 C8 -1.7(3) . . . . ?
O7 C7 C8 N9 -180.0(3) . . . . ?
O6 C7 C8 N9 0.6(3) . . . . ?
O7 C7 C8 C17 -56.7(4) . . . . ?
O6 C7 C8 C17 123.8(3) . . . . ?
C7 C8 N9 P5 0.9(3) . . . . ?
C17 C8 N9 P5 -120.2(2) . . . . ?
N4 P5 N9 C8 88.0(2) . . . . ?
O6 P5 N9 C8 -1.6(2) . . . . ?
O1 P5 N9 C8 177.8(2) . . . . ?
N4 C3 C10 C11 60.2(3) . . . . ?
C2 C3 C10 C11 -58.2(3) . . . . ?
C3 C10 C11 C12 96.2(3) . . . . ?
C3 C10 C11 C16 -86.3(3) . . . . ?
C16 C11 C12 C13 -0.9(5) . . . . ?
C10 C11 C12 C13 176.7(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C14 C15 C16 C11 0.9(5) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C10 C11 C16 C15 -177.4(3) . . . . ?
N9 C8 C17 C18 -71.7(3) . . . . ?
C7 C8 C17 C18 171.0(3) . . . . ?
C8 C17 C18 C19 77.2(4) . . . . ?
C8 C17 C18 C23 -99.9(3) . . . . ?
C23 C18 C19 C20 0.6(5) . . . . ?
C17 C18 C19 C20 -176.6(3) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C18 -0.2(5) . . . . ?
C19 C18 C23 C22 -0.3(5) . . . . ?
C17 C18 C23 C22 176.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9A O7 0.86 2.52 3.048(3) 120.6 1_655 y
C12 H12A O7 0.93 2.49 3.189(4) 131.7 1_645 y
N4 H4A O2 0.86 2.15 2.965(3) 158.6 1_455 y
C22 H22A CgA 0.93 3.34 4.145(3) 146.27 3_656 y

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.043
_exptl_crystal_preparation       'acetone/petroleum ether (v/v = 1:1)'

# Attachment 'CCDC-721775(4b)-090609.cif'

data_h
_database_code_depnum_ccdc_archive 'CCDC 721775'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(3R, 5\D, 8R)-3,8-Dibenzyl-1,6-dioxa-4,9-diaza-5\L5-phosphaspiro
[4.4]-nonane-2,7-dione
;
_chemical_name_common            
;
(3R, 5cdelta, 8R)-3,8-Dibenzyl-1,6-dioxa-4,9-diaza-5clambda5-
phosphaspiro (4.4)-nonane-2,7-dione
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 N2 O4 P'
_chemical_formula_sum            'C18 H19 N2 O4 P'
_chemical_formula_weight         358.32

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_chemical_absolute_configuration syn

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                   6.0474(2)
_cell_length_b                   8.3290(3)
_cell_length_c                   34.270(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1726.14(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3865
_cell_measurement_theta_min      2.4325
_cell_measurement_theta_max      32.5199

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_T_max  0.9640
_exptl_absorpt_process_details   'CrysAlis RED; (Oxford Diffraction, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Gemini S Ultra CCD Area Detector'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5918
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2917
_reflns_number_gt                2695
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. The atoms O7 and C11
show high ADP max/min ratio after initial full-matrix least-squares
refinement which were then refined with isotropic restraints.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.0528P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     227
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1442
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.248
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.3542(5) 0.3517(4) 0.95301(10) 0.0228(8) Uani 1 1 d . . .
C2 C 0.3623(8) 0.5025(6) 0.96479(13) 0.0201(10) Uani 1 1 d . . .
O2 O 0.5355(5) 0.5753(4) 0.96791(11) 0.0260(8) Uani 1 1 d . . .
C3 C 0.1348(8) 0.5679(6) 0.97362(14) 0.0236(11) Uani 1 1 d . . .
H3A H 0.1256 0.5900 1.0017 0.028 Uiso 1 1 calc R . .
N4 N -0.0134(6) 0.4371(5) 0.96462(12) 0.0241(10) Uani 1 1 d . . .
H4A H -0.1543 0.4504 0.9659 0.029 Uiso 1 1 calc R . .
P5 P 0.08930(19) 0.26561(15) 0.95221(4) 0.0206(3) Uani 1 1 d . . .
H5 H 0.1487 0.1586 0.9811 0.026(14) Uiso 1 1 d R . .
O6 O -0.1752(5) 0.1830(4) 0.95151(11) 0.0274(8) Uani 1 1 d . . .
O7 O -0.4132(6) 0.0534(4) 0.91334(14) 0.0432(11) Uani 1 1 d U . .
C7 C -0.2361(9) 0.1129(6) 0.91843(18) 0.0304(13) Uani 1 1 d . . .
C8 C -0.0502(8) 0.1182(6) 0.88824(16) 0.0241(11) Uani 1 1 d . . .
H9A H -0.0026 0.0085 0.8823 0.029 Uiso 1 1 calc R . .
N9 N 0.1274(7) 0.2025(5) 0.90768(12) 0.0269(10) Uani 1 1 d . . .
H10A H 0.2510 0.2190 0.8960 0.032 Uiso 1 1 calc R . .
C10 C 0.0864(8) 0.7229(6) 0.95158(16) 0.0275(11) Uani 1 1 d . . .
H10B H -0.0610 0.7590 0.9585 0.033 Uiso 1 1 calc R . .
H10C H 0.1899 0.8045 0.9602 0.033 Uiso 1 1 calc R . .
C11 C 0.1007(8) 0.7094(5) 0.90774(15) 0.0219(10) Uani 1 1 d U . .
C12 C 0.2934(8) 0.7528(7) 0.88831(17) 0.0333(13) Uani 1 1 d . . .
H12A H 0.4168 0.7850 0.9025 0.040 Uiso 1 1 calc R . .
C13 C 0.3022(10) 0.7484(8) 0.84800(18) 0.0420(15) Uani 1 1 d . . .
H13A H 0.4313 0.7785 0.8352 0.050 Uiso 1 1 calc R . .
C14 C 0.1218(11) 0.6999(7) 0.82679(17) 0.0400(14) Uani 1 1 d . . .
H14A H 0.1286 0.6968 0.7997 0.048 Uiso 1 1 calc R . .
C15 C -0.0687(10) 0.6559(7) 0.84573(17) 0.0374(14) Uani 1 1 d . . .
H15A H -0.1907 0.6219 0.8314 0.045 Uiso 1 1 calc R . .
C16 C -0.0802(9) 0.6618(6) 0.88590(16) 0.0272(11) Uani 1 1 d . . .
H16A H -0.2109 0.6334 0.8984 0.033 Uiso 1 1 calc R . .
C17 C -0.1316(9) 0.1992(7) 0.85077(17) 0.0341(13) Uani 1 1 d . . .
H17A H -0.2704 0.1505 0.8429 0.041 Uiso 1 1 calc R . .
H17B H -0.1593 0.3119 0.8560 0.041 Uiso 1 1 calc R . .
C18 C 0.0315(9) 0.1850(7) 0.81788(17) 0.0336(13) Uani 1 1 d . . .
C19 C 0.2191(11) 0.2784(8) 0.8161(2) 0.0468(17) Uani 1 1 d . . .
H19A H 0.2442 0.3562 0.8351 0.056 Uiso 1 1 calc R . .
C20 C 0.3705(11) 0.2571(10) 0.7862(2) 0.0557(18) Uani 1 1 d . . .
H20A H 0.4959 0.3216 0.7852 0.067 Uiso 1 1 calc R . .
C21 C 0.3379(14) 0.1418(10) 0.7581(2) 0.060(2) Uani 1 1 d . . .
H21A H 0.4413 0.1279 0.7383 0.073 Uiso 1 1 calc R . .
C22 C 0.1538(13) 0.0483(9) 0.75937(19) 0.0557(19) Uani 1 1 d . . .
H22A H 0.1307 -0.0300 0.7404 0.067 Uiso 1 1 calc R . .
C23 C 0.0008(11) 0.0701(8) 0.78898(18) 0.0431(16) Uani 1 1 d . . .
H23A H -0.1254 0.0063 0.7895 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0109(15) 0.0287(19) 0.0289(18) -0.0009(17) 0.0000(15) 0.0021(14)
C2 0.026(3) 0.016(2) 0.019(2) 0.0019(19) -0.0018(19) 0.006(2)
O2 0.0156(17) 0.0261(19) 0.036(2) -0.0044(16) -0.0029(15) -0.0061(15)
C3 0.024(3) 0.026(3) 0.021(2) -0.008(2) -0.002(2) 0.000(2)
N4 0.0119(18) 0.032(2) 0.028(2) 0.0001(19) 0.0004(17) -0.0048(18)
P5 0.0145(5) 0.0214(6) 0.0259(6) 0.0036(6) -0.0013(5) 0.0002(6)
O6 0.0162(15) 0.0241(18) 0.042(2) 0.0048(18) 0.0033(17) -0.0070(15)
O7 0.0188(18) 0.028(2) 0.083(3) -0.021(2) 0.001(2) -0.0132(19)
C7 0.030(3) 0.012(3) 0.050(4) -0.005(3) -0.003(3) 0.003(2)
C8 0.017(2) 0.014(2) 0.042(3) -0.004(2) -0.006(2) 0.003(2)
N9 0.016(2) 0.034(2) 0.031(2) -0.0054(19) 0.0004(18) -0.0045(19)
C10 0.023(2) 0.022(3) 0.037(3) -0.008(3) -0.004(2) 0.004(2)
C11 0.023(2) 0.006(2) 0.037(3) 0.0018(19) -0.003(2) 0.008(2)
C12 0.025(3) 0.026(3) 0.048(3) 0.002(3) -0.002(2) -0.003(3)
C13 0.035(3) 0.044(4) 0.047(3) 0.011(3) 0.010(3) -0.002(3)
C14 0.054(4) 0.033(3) 0.033(3) 0.004(3) 0.003(3) 0.004(3)
C15 0.041(3) 0.037(3) 0.035(3) 0.002(3) -0.011(3) 0.001(3)
C16 0.022(2) 0.019(3) 0.041(3) -0.001(2) -0.004(2) 0.002(2)
C17 0.027(3) 0.028(3) 0.047(3) -0.003(3) -0.013(3) 0.009(2)
C18 0.038(3) 0.022(3) 0.040(3) 0.004(2) -0.013(3) 0.005(2)
C19 0.057(4) 0.039(4) 0.044(4) 0.006(3) -0.012(3) 0.008(3)
C20 0.049(4) 0.063(5) 0.055(4) 0.021(4) -0.006(3) -0.010(4)
C21 0.073(5) 0.074(5) 0.035(4) 0.011(4) 0.003(4) 0.010(5)
C22 0.074(5) 0.059(5) 0.034(4) -0.006(3) -0.009(4) 0.009(4)
C23 0.053(4) 0.039(4) 0.037(3) 0.000(3) -0.012(3) 0.006(3)

_geom_special_details            
;
CgA is the centroid of the C18-C23 phenyl ring. 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.320(6) . ?
O1 P5 1.755(3) . ?
C2 O2 1.215(6) . ?
C2 C3 1.511(6) . ?
C3 N4 1.444(6) . ?
C3 C10 1.524(7) . ?
C3 H3A 0.9800 . ?
N4 P5 1.615(4) . ?
N4 H4A 0.8600 . ?
P5 N9 1.631(4) . ?
P5 O6 1.742(3) . ?
P5 H5 1.3791 . ?
O6 C7 1.327(7) . ?
O7 C7 1.192(6) . ?
C7 C8 1.528(8) . ?
C8 N9 1.446(6) . ?
C8 C17 1.532(7) . ?
C8 H9A 0.9800 . ?
N9 H10A 0.8600 . ?
C10 C11 1.509(7) . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C16 1.383(7) . ?
C11 C12 1.390(7) . ?
C12 C13 1.383(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.372(9) . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.502(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.377(9) . ?
C18 C23 1.390(8) . ?
C19 C20 1.386(10) . ?
C19 H19A 0.9300 . ?
C20 C21 1.374(10) . ?
C20 H20A 0.9300 . ?
C21 C22 1.359(10) . ?
C21 H21A 0.9300 . ?
C22 C23 1.385(9) . ?
C22 H22A 0.9300 . ?
C23 H23A 0.9300 . ?

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
_geom_angle_publ_flag
C2 O1 P5 115.3(3) . . ?
O2 C2 O1 122.3(4) . . ?
O2 C2 C3 126.0(4) . . ?
O1 C2 C3 111.7(4) . . ?
N4 C3 C2 104.5(4) . . ?
N4 C3 C10 114.4(4) . . ?
C2 C3 C10 112.4(4) . . ?
N4 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
C10 C3 H3A 108.4 . . ?
C3 N4 P5 119.0(3) . . ?
C3 N4 H4A 120.5 . . ?
P5 N4 H4A 120.5 . . ?
N4 P5 N9 125.9(2) . . ?
N4 P5 O6 90.00(19) . . ?
N9 P5 O6 89.4(2) . . ?
N4 P5 O1 89.16(19) . . ?
N9 P5 O1 91.00(19) . . ?
O6 P5 O1 179.15(19) . . ?
N4 P5 H5 118.9 . . ?
N9 P5 H5 115.2 . . ?
O6 P5 H5 89.6 . . ?
O1 P5 H5 90.9 . . ?
C7 O6 P5 116.1(3) . . ?
O7 C7 O6 123.8(5) . . ?
O7 C7 C8 125.0(5) . . ?
O6 C7 C8 111.2(4) . . ?
N9 C8 C7 104.4(4) . . ?
N9 C8 C17 114.3(4) . . ?
C7 C8 C17 110.1(4) . . ?
N9 C8 H9A 109.3 . . ?
C7 C8 H9A 109.3 . . ?
C17 C8 H9A 109.3 . . ?
C8 N9 P5 118.9(3) . . ?
C8 N9 H10A 120.6 . . ?
P5 N9 H10A 120.6 . . ?
C11 C10 C3 114.8(4) . . ?
C11 C10 H10B 108.6 . . ?
C3 C10 H10B 108.6 . . ?
C11 C10 H10C 108.6 . . ?
C3 C10 H10C 108.6 . . ?
H10B C10 H10C 107.6 . . ?
C16 C11 C12 118.6(5) . . ?
C16 C11 C10 121.0(5) . . ?
C12 C11 C10 120.4(5) . . ?
C13 C12 C11 120.3(5) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 119.7(6) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.3(6) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 120.7(5) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
C18 C17 C8 112.5(4) . . ?
C18 C17 H17A 109.1 . . ?
C8 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C8 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C23 117.9(6) . . ?
C19 C18 C17 122.0(5) . . ?
C23 C18 C17 120.1(6) . . ?
C18 C19 C20 120.3(7) . . ?
C18 C19 H19A 119.9 . . ?
C20 C19 H19A 119.9 . . ?
C21 C20 C19 120.9(7) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C22 C21 C20 119.7(7) . . ?
C22 C21 H21A 120.1 . . ?
C20 C21 H21A 120.1 . . ?
C21 C22 C23 119.7(7) . . ?
C21 C22 H22A 120.2 . . ?
C23 C22 H22A 120.2 . . ?
C22 C23 C18 121.5(7) . . ?
C22 C23 H23A 119.2 . . ?
C18 C23 H23A 119.2 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P5 O1 C2 O2 177.7(4) . . . . ?
P5 O1 C2 C3 -2.0(5) . . . . ?
O2 C2 C3 N4 178.9(5) . . . . ?
O1 C2 C3 N4 -1.4(5) . . . . ?
O2 C2 C3 C10 54.2(6) . . . . ?
O1 C2 C3 C10 -126.1(4) . . . . ?
C2 C3 N4 P5 4.8(5) . . . . ?
C10 C3 N4 P5 128.2(4) . . . . ?
C3 N4 P5 N9 -95.8(4) . . . . ?
C3 N4 P5 O6 175.0(4) . . . . ?
C3 N4 P5 O1 -5.2(4) . . . . ?
C2 O1 P5 N4 4.1(3) . . . . ?
C2 O1 P5 N9 129.9(3) . . . . ?
C2 O1 P5 O6 12(13) . . . . ?
N4 P5 O6 C7 124.4(4) . . . . ?
N9 P5 O6 C7 -1.5(4) . . . . ?
O1 P5 O6 C7 116(13) . . . . ?
P5 O6 C7 O7 -178.8(4) . . . . ?
P5 O6 C7 C8 1.5(5) . . . . ?
O7 C7 C8 N9 179.6(5) . . . . ?
O6 C7 C8 N9 -0.7(6) . . . . ?
O7 C7 C8 C17 56.4(7) . . . . ?
O6 C7 C8 C17 -123.9(5) . . . . ?
C7 C8 N9 P5 -0.4(5) . . . . ?
C17 C8 N9 P5 120.0(4) . . . . ?
N4 P5 N9 C8 -88.5(4) . . . . ?
O6 P5 N9 C8 1.0(4) . . . . ?
O1 P5 N9 C8 -178.2(4) . . . . ?
N4 C3 C10 C11 -60.5(6) . . . . ?
C2 C3 C10 C11 58.5(6) . . . . ?
C3 C10 C11 C16 87.2(6) . . . . ?
C3 C10 C11 C12 -96.2(6) . . . . ?
C16 C11 C12 C13 0.1(8) . . . . ?
C10 C11 C12 C13 -176.6(5) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C13 C14 C15 0.2(10) . . . . ?
C13 C14 C15 C16 0.7(10) . . . . ?
C14 C15 C16 C11 -1.1(9) . . . . ?
C12 C11 C16 C15 0.7(8) . . . . ?
C10 C11 C16 C15 177.4(4) . . . . ?
N9 C8 C17 C18 71.9(6) . . . . ?
C7 C8 C17 C18 -171.0(5) . . . . ?
C8 C17 C18 C19 -76.5(7) . . . . ?
C8 C17 C18 C23 100.5(6) . . . . ?
C23 C18 C19 C20 0.1(9) . . . . ?
C17 C18 C19 C20 177.2(6) . . . . ?
C18 C19 C20 C21 -0.7(10) . . . . ?
C19 C20 C21 C22 0.6(11) . . . . ?
C20 C21 C22 C23 0.0(11) . . . . ?
C21 C22 C23 C18 -0.6(10) . . . . ?
C19 C18 C23 C22 0.5(9) . . . . ?
C17 C18 C23 C22 -176.7(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H10A O7 0.86 2.53 3.049(6) 120.1 1_655 y
C12 H12A O7 0.93 2.49 3.187(7) 131.9 1_665 y
N4 H4A O2 0.86 2.15 2.963(5) 158.4 1_455 y
C22 H22A CgA 0.93 3.33 4.135(3) 145.55 3_546 y

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.072
_exptl_crystal_preparation       'acetone/petroleum ether (v/v = 1:1)'