# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Valery Brel'
'Vitaly K. Belsky'
'Peter J. Stang'
'Adam I. Stash'
'Valery E. Zavodnik'

_publ_contact_author_name        'Prof Valery Brel'
_publ_contact_author_address     
;
Laboratory of chemistry of fluorine compounds
Institute of Physiologically Active Compounds
Russian Academy of Sciences
Severny proezd, 1
Chernogolovka
Moscow region
142432
RUSSIAN FEDERATION
;

_publ_contact_author_email       BREL@IPAC.AC.RU

_publ_requested_journal          'Organic & Biomolecular Chemistry'

_publ_section_title              
;
SYNTHESIS AND MOLECULAR STRUCTURE OF NEW ACYCLIC
ANALOGUES OF NUCLEOTIDES WITH A 1,2-ALKADIENIC SKELETON.
;

data_Compound_18
_database_code_CSD               218714

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H26 N5 O3 P'
_chemical_formula_weight         379.40

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.047(6)
_cell_length_b                   11.272(2)
_cell_length_c                   13.562(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.05(3)
_cell_angle_gamma                90.00
_cell_volume                     4176.8(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    20
_cell_measurement_theta_min      11.2
_cell_measurement_theta_max      12.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  beta-filter
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       theta/2theta
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1018
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         24.79
_reflns_number_total             997
_reflns_number_gt                997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1128P)²+14.4371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         997
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
P P 0.35774(11) 0.0797(4) 0.0526(3) 0.1042(12) Uani 1 1 d . . .
O1 O 0.3084(2) 0.0932(8) 0.0643(5) 0.122(3) Uani 1 1 d . . .
O2 O 0.3976(3) 0.0992(9) 0.1513(7) 0.126(3) Uani 1 1 d . . .
O3 O 0.3721(3) -0.0469(9) 0.0161(8) 0.136(3) Uani 1 1 d . . .
N1 N 0.3204(2) 0.4541(6) -0.0159(4) 0.063(2) Uani 1 1 d . . .
N2 N 0.3342(3) 0.4657(7) 0.1534(5) 0.071(2) Uani 1 1 d . . .
N3 N 0.4553(2) 0.5604(7) 0.1199(4) 0.066(2) Uani 1 1 d . . .
N4 N 0.3997(2) 0.5204(7) -0.0392(4) 0.067(2) Uani 1 1 d . . .
N5 N 0.4356(2) 0.5427(7) 0.2761(5) 0.072(2) Uani 1 1 d . . .
C1 C 0.3732(5) 0.1721(12) -0.0406(10) 0.108(4) Uani 1 1 d . . .
C2 C 0.3392(4) 0.2352(12) -0.0956(8) 0.087(3) Uani 1 1 d . . .
C3 C 0.3050(4) 0.3010(12) -0.1472(7) 0.081(3) Uani 1 1 d . . .
C4 C 0.2954(3) 0.4254(10) -0.1197(6) 0.075(3) Uani 1 1 d . . .
C5 C 0.2712(5) 0.2588(12) -0.2446(8) 0.130(4) Uani 1 1 d . . .
C6 C 0.4325(10) 0.1803(19) -0.0365(14) 0.191(10) Uani 1 1 d . . .
C7 C 0.4388(8) 0.134(2) -0.1136(19) 0.232(10) Uani 1 1 d . . .
C8 C 0.4975(6) 0.1383(16) -0.1067(15) 0.198(8) Uani 1 1 d . . .
C9 C 0.3023(3) 0.4381(9) 0.0691(6) 0.071(3) Uani 1 1 d . . .
C10 C 0.3754(3) 0.4994(8) 0.1215(5) 0.058(2) Uani 1 1 d . . .
C11 C 0.4219(3) 0.5342(8) 0.1743(6) 0.060(2) Uani 1 1 d . . .
C12 C 0.4418(3) 0.5529(9) 0.0187(6) 0.070(3) Uani 1 1 d . . .
C13 C 0.3676(3) 0.4932(8) 0.0181(6) 0.057(2) Uani 1 1 d . . .
C14 C 0.3939(7) 0.182(2) 0.2187(19) 0.232(12) Uani 1 1 d . . .
C15 C 0.4270(11) 0.2114(17) 0.2880(18) 0.255(12) Uani 1 1 d . . .
C16 C 0.3619(6) -0.154(2) 0.0639(13) 0.156(6) Uani 1 1 d . . .
C17 C 0.3205(6) -0.2098(16) 0.0053(13) 0.175(6) Uani 1 1 d . . .
H1N H 0.4121 0.5059 0.3163 0.085 Uiso 1 1 d . . .
H2N H 0.4738 0.5720 0.3007 0.085 Uiso 1 1 d . . .
H41 H 0.2576 0.4470 -0.1290 0.085 Uiso 1 1 d . . .
H42 H 0.3075 0.4927 -0.1586 0.085 Uiso 1 1 d . . .
H51 H 0.2356 0.2628 -0.2462 0.085 Uiso 1 1 d . . .
H52 H 0.2821 0.1757 -0.2593 0.085 Uiso 1 1 d . . .
H53 H 0.2795 0.3183 -0.2909 0.085 Uiso 1 1 d . . .
H61 H 0.4550 0.1416 0.0253 0.085 Uiso 1 1 d . . .
H62 H 0.4468 0.2614 -0.0359 0.085 Uiso 1 1 d . . .
H71 H 0.4151 0.1653 -0.1697 0.085 Uiso 1 1 d . . .
H72 H 0.4242 0.0459 -0.1084 0.085 Uiso 1 1 d . . .
H81 H 0.5082 0.0979 -0.1660 0.085 Uiso 1 1 d . . .
H82 H 0.5106 0.2192 -0.1086 0.085 Uiso 1 1 d . . .
H83 H 0.5197 0.1002 -0.0474 0.085 Uiso 1 1 d . . .
H9 H 0.2645 0.4265 0.0595 0.085 Uiso 1 1 d . . .
H12 H 0.4715 0.5644 -0.0254 0.085 Uiso 1 1 d . . .
H141 H 0.3655 0.1681 0.2520 0.085 Uiso 1 1 d . . .
H142 H 0.3841 0.2614 0.1862 0.085 Uiso 1 1 d . . .
H151 H 0.4218 0.2760 0.3416 0.085 Uiso 1 1 d . . .
H152 H 0.4394 0.1440 0.3417 0.085 Uiso 1 1 d . . .
H153 H 0.4582 0.2388 0.2750 0.085 Uiso 1 1 d . . .
H161 H 0.3555 -0.1430 0.1332 0.085 Uiso 1 1 d . . .
H162 H 0.3890 -0.2135 0.0766 0.085 Uiso 1 1 d . . .
H171 H 0.3091 -0.2853 0.0287 0.085 Uiso 1 1 d . . .
H172 H 0.2907 -0.1581 -0.0083 0.085 Uiso 1 1 d . . .
H173 H 0.3244 -0.2290 -0.0653 0.085 Uiso 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P O1 1.435(6) . ?
P O2 1.554(8) . ?
P O3 1.591(9) . ?
P C1 1.766(13) . ?
O2 C14 1.323(19) . ?
O3 C16 1.427(18) . ?
N1 C13 1.372(9) . ?
N1 C9 1.373(9) . ?
N1 C4 1.460(10) . ?
N2 C9 1.320(9) . ?
N2 C10 1.377(9) . ?
N3 C12 1.342(9) . ?
N3 C11 1.350(9) . ?
N4 C12 1.315(10) . ?
N4 C13 1.348(9) . ?
N5 C11 1.351(9) . ?
C1 C2 1.285(15) . ?
C1 C6 1.65(3) . ?
C2 C3 1.288(15) . ?
C3 C4 1.491(13) . ?
C3 C5 1.518(13) . ?
C6 C7 1.22(2) . ?
C7 C8 1.63(2) . ?
C10 C13 1.371(10) . ?
C10 C11 1.395(11) . ?
C14 C15 1.21(2) . ?
C16 C17 1.40(2) . ?

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
O1 P O2 114.4(5) . . ?
O1 P O3 116.5(5) . . ?
O2 P O3 102.2(6) . . ?
O1 P C1 114.6(6) . . ?
O2 P C1 106.7(6) . . ?
O3 P C1 100.7(6) . . ?
C14 O2 P 122.8(11) . . ?
C16 O3 P 121.8(10) . . ?
C13 N1 C9 105.8(6) . . ?
C13 N1 C4 127.7(7) . . ?
C9 N1 C4 126.3(7) . . ?
C9 N2 C10 104.2(6) . . ?
C12 N3 C11 118.4(7) . . ?
C12 N4 C13 110.3(6) . . ?
C2 C1 C6 126.7(12) . . ?
C2 C1 P 118.1(9) . . ?
C6 C1 P 114.6(11) . . ?
C1 C2 C3 177.5(12) . . ?
C2 C3 C4 124.0(9) . . ?
C2 C3 C5 122.3(12) . . ?
C4 C3 C5 113.6(11) . . ?
N1 C4 C3 112.1(8) . . ?
C7 C6 C1 107(2) . . ?
C6 C7 C8 106(2) . . ?
N2 C9 N1 113.0(7) . . ?
C13 C10 N2 110.9(7) . . ?
C13 C10 C11 117.0(8) . . ?
N2 C10 C11 132.1(7) . . ?
N3 C11 N5 118.1(7) . . ?
N3 C11 C10 117.7(7) . . ?
N5 C11 C10 124.2(8) . . ?
N4 C12 N3 129.4(7) . . ?
N4 C13 C10 127.2(8) . . ?
N4 C13 N1 126.7(7) . . ?
C10 C13 N1 106.1(7) . . ?
C15 C14 O2 124(2) . . ?
C17 C16 O3 110.3(14) . . ?

_diffrn_measured_fraction_theta_max 0.278
_diffrn_reflns_theta_full        24.79
_diffrn_measured_fraction_theta_full 0.278
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043

data_compound_2f
_database_code_CSD               218715

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 N2 O5 P'
_chemical_formula_weight         327.29

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.135(3)
_cell_length_b                   8.272(2)
_cell_length_c                   14.408(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.97(3)
_cell_angle_gamma                90.00
_cell_volume                     1611.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      11.3
_cell_measurement_theta_max      12.7

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  beta-filter
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       theta/2theta
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1890
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1810
_reflns_number_gt                1810
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0734P)²+0.6170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0047(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1810
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
P P 0.16812(7) 0.66743(10) 0.66819(7) 0.0712(3) Uani 1 1 d . . .
O1 O 0.47928(15) 0.7044(2) 0.50469(12) 0.0577(5) Uani 1 1 d . . .
O2 O 0.51811(17) 0.3514(2) 0.75229(15) 0.0711(6) Uani 1 1 d . . .
O3A O 0.1900(5) 0.8325(9) 0.7410(4) 0.0653(15) Uani 0.559(11) 1 d P . .
O3B O 0.2229(5) 0.7485(11) 0.7479(3) 0.059(2) Uani 0.441(11) 1 d P . .
O4A O 0.0473(5) 0.7064(9) 0.6222(5) 0.0577(15) Uani 0.559(11) 1 d P . .
O4B O 0.0663(6) 0.6489(10) 0.6531(6) 0.0539(19) Uani 0.441(11) 1 d P . .
O5A O 0.2262(7) 0.5316(7) 0.7290(5) 0.110(3) Uani 0.559(11) 1 d P . .
O5B O 0.1641(4) 0.4778(6) 0.6725(5) 0.062(2) Uani 0.441(11) 1 d P . .
N1 N 0.45821(14) 0.7984(2) 0.64553(14) 0.0429(5) Uani 1 1 d . . .
N2 N 0.49922(16) 0.5328(3) 0.63198(15) 0.0480(5) Uani 1 1 d . . .
C1 C 0.20749(19) 0.7044(3) 0.56336(18) 0.0478(6) Uani 1 1 d . . .
C2 C 0.25818(18) 0.8351(3) 0.56024(17) 0.0424(6) Uani 1 1 d . . .
C3 C 0.31238(18) 0.9624(3) 0.56070(15) 0.0396(5) Uani 1 1 d . . .
C4 C 0.4229(2) 0.9556(3) 0.6028(2) 0.0477(6) Uani 1 1 d . . .
C5 C 0.2715(3) 1.1245(3) 0.5225(2) 0.0569(8) Uani 1 1 d . . .
C6 C 0.1816(3) 0.5768(4) 0.4848(2) 0.0647(8) Uani 1 1 d . . .
C7 C 0.2118(2) 0.6151(4) 0.3957(2) 0.0585(7) Uani 1 1 d . . .
C8 C 0.1858(4) 0.4829(4) 0.3203(3) 0.0788(10) Uani 1 1 d . . .
C9 C 0.2092(4) 0.5236(7) 0.2273(3) 0.0904(12) Uani 1 1 d . . .
C10 C 0.47872(18) 0.6807(3) 0.58848(18) 0.0432(6) Uani 1 1 d . . .
C11 C 0.49957(18) 0.4923(3) 0.72453(18) 0.0478(6) Uani 1 1 d . . .
C12 C 0.47894(18) 0.6225(3) 0.78156(17) 0.0452(6) Uani 1 1 d . . .
C13 C 0.45850(18) 0.7669(3) 0.73914(16) 0.0453(6) Uani 1 1 d . . .
C14 C 0.4795(3) 0.5954(5) 0.8847(2) 0.0630(8) Uani 1 1 d . . .
H2N H 0.511(2) 0.456(4) 0.598(2) 0.060(8) Uiso 1 1 d . . .
H41 H 0.4450(19) 1.035(3) 0.654(2) 0.054(7) Uiso 1 1 d . . .
H42 H 0.4518(19) 0.977(3) 0.5517(19) 0.051(7) Uiso 1 1 d . . .
H51 H 0.281(3) 1.202(5) 0.580(3) 0.096(11) Uiso 1 1 d . . .
H52 H 0.304(3) 1.165(4) 0.478(3) 0.088(11) Uiso 1 1 d . . .
H53 H 0.203(3) 1.113(5) 0.483(3) 0.105(13) Uiso 1 1 d . . .
H61 H 0.109(3) 0.546(5) 0.469(3) 0.106(13) Uiso 1 1 d . . .
H62 H 0.207(3) 0.471(5) 0.513(3) 0.103(12) Uiso 1 1 d . . .
H71 H 0.178(2) 0.724(4) 0.368(2) 0.072(9) Uiso 1 1 d . . .
H72 H 0.276(3) 0.638(4) 0.412(2) 0.069(9) Uiso 1 1 d . . .
H81 H 0.113(3) 0.465(5) 0.309(3) 0.109(14) Uiso 1 1 d . . .
H82 H 0.230(3) 0.400(6) 0.345(3) 0.114(15) Uiso 1 1 d . . .
H91 H 0.282(4) 0.544(6) 0.244(3) 0.127(16) Uiso 1 1 d . . .
H92 H 0.187(4) 0.437(7) 0.181(4) 0.142(18) Uiso 1 1 d . . .
H93 H 0.177(3) 0.627(6) 0.201(3) 0.120(16) Uiso 1 1 d . . .
H13 H 0.4387(18) 0.860(3) 0.7725(18) 0.046(7) Uiso 1 1 d . . .
H141 H 0.466(3) 0.698(5) 0.916(3) 0.099(12) Uiso 1 1 d . . .
H142 H 0.429(3) 0.524(4) 0.892(2) 0.077(10) Uiso 1 1 d . . .
H143 H 0.546(4) 0.563(5) 0.922(3) 0.119(15) Uiso 1 1 d . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P O3B 1.360(6) . ?
P O4B 1.400(8) . ?
P O5A 1.511(5) . ?
P O5B 1.572(5) . ?
P O4A 1.673(7) . ?
P O3A 1.694(6) . ?
P C1 1.782(3) . ?
O1 C10 1.225(3) . ?
O2 C11 1.235(3) . ?
O3A O3B 0.826(6) . ?
O3B O5A 1.818(9) . ?
O4A O4B 0.653(7) . ?
O5A O5B 1.102(7) . ?
N1 C10 1.359(3) . ?
N1 C13 1.373(3) . ?
N1 C4 1.463(3) . ?
N2 C10 1.367(3) . ?
N2 C11 1.374(3) . ?
C1 C2 1.305(3) . ?
C1 C6 1.513(4) . ?
C2 C3 1.301(3) . ?
C3 C5 1.500(3) . ?
C3 C4 1.503(4) . ?
C6 C7 1.500(4) . ?
C7 C8 1.509(4) . ?
C8 C9 1.509(6) . ?
C11 C12 1.435(3) . ?
C12 C13 1.335(4) . ?
C12 C14 1.501(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
_geom_angle_publ_flag
O3B P O4B 119.4(4) . . ?
O3B P O5A 78.3(4) . . ?
O4B P O5A 111.7(7) . . ?
O3B P O5B 118.5(3) . . ?
O4B P O5B 81.3(5) . . ?
O5A P O5B 41.8(3) . . ?
O3B P O4A 120.2(5) . . ?
O4B P O4A 22.4(3) . . ?
O5A P O4A 133.8(5) . . ?
O5B P O4A 99.4(4) . . ?
O3B P O3A 28.8(3) . . ?
O4B P O3A 100.2(4) . . ?
O5A P O3A 105.7(3) . . ?
O5B P O3A 141.4(3) . . ?
O4A P O3A 94.1(4) . . ?
O3B P C1 113.0(2) . . ?
O4B P C1 116.7(4) . . ?
O5A P C1 111.5(2) . . ?
O5B P C1 103.2(2) . . ?
O4A P C1 99.6(3) . . ?
O3A P C1 109.9(2) . . ?
O3B O3A P 52.5(5) . . ?
O3A O3B P 98.7(7) . . ?
O3A O3B O5A 148.3(9) . . ?
P O3B O5A 54.5(3) . . ?
O4B O4A P 54.6(10) . . ?
O4A O4B P 103.0(12) . . ?
O5B O5A P 72.0(5) . . ?
O5B O5A O3B 117.4(6) . . ?
P O5A O3B 47.1(2) . . ?
O5A O5B P 66.2(4) . . ?
C10 N1 C13 121.2(2) . . ?
C10 N1 C4 119.26(19) . . ?
C13 N1 C4 119.1(2) . . ?
C10 N2 C11 127.2(2) . . ?
C2 C1 C6 124.6(2) . . ?
C2 C1 P 118.8(2) . . ?
C6 C1 P 116.60(19) . . ?
C3 C2 C1 177.1(3) . . ?
C2 C3 C5 124.0(2) . . ?
C2 C3 C4 120.9(2) . . ?
C5 C3 C4 115.2(2) . . ?
N1 C4 C3 112.9(2) . . ?
C7 C6 C1 115.2(2) . . ?
C6 C7 C8 113.1(3) . . ?
C9 C8 C7 114.0(3) . . ?
O1 C10 N1 123.0(2) . . ?
O1 C10 N2 122.3(2) . . ?
N1 C10 N2 114.7(2) . . ?
O2 C11 N2 119.0(2) . . ?
O2 C11 C12 125.6(2) . . ?
N2 C11 C12 115.4(2) . . ?
C13 C12 C11 117.6(2) . . ?
C13 C12 C14 121.7(2) . . ?
C11 C12 C14 120.8(3) . . ?
C12 C13 N1 123.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.640
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.640
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.040



