# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DPA_MBPz

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C8 H11 O6 P2, 0.5(C8 H10 O6 P2), C11 H18 N4, 0.4(H2O)'
_chemical_formula_sum            'C23 H34.8 N4 O9.4 P3'
_chemical_formula_weight         610.66

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.3768(9)
_cell_length_b                   21.2361(15)
_cell_length_c                   12.4255(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.766(4)
_cell_angle_gamma                90.00
_cell_volume                     2949.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    145
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      26.47

_exptl_crystal_description       cubic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1281.4
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35500
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.1006
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.47
_reflns_number_total             6042
_reflns_number_gt                3066
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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. 

The water oxygen O10, with partial occupancy, was refined isotropically with
s.o.f. converged to 0.395150. It may be noted that the H atoms of water molecule
were not located in a difference fourier map though the molecular formula reported
in CIF includes the hydrogen of the water molecule.
;

_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)+(0.1000P)²+0.0093P] where P=(Fo²+2Fc²)/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_number_reflns         6042
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1821
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_restrained_S_all      0.916
_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
P3 P 0.21627(8) 0.03248(4) 0.63731(8) 0.0381(3) Uani 1 1 d . . .
P2 P 0.96075(9) 0.33810(5) 0.93410(10) 0.0475(3) Uani 1 1 d . . .
P1 P 0.29082(9) 0.21224(5) 0.87688(9) 0.0462(3) Uani 1 1 d . . .
O1 O 0.3500(2) 0.16317(11) 0.9536(2) 0.0510(7) Uani 1 1 d . . .
O2 O 0.2983(3) 0.19739(12) 0.7554(2) 0.0599(8) Uani 1 1 d . . .
H2E H 0.2878 0.1596 0.7440 0.090 Uiso 1 1 calc R . .
O3 O 0.1594(2) 0.22225(13) 0.8842(3) 0.0666(9) Uani 1 1 d . . .
H3E H 0.1497 0.2586 0.9029 0.100 Uiso 1 1 calc R . .
O4 O 1.0907(2) 0.32415(12) 0.9361(3) 0.0715(9) Uani 1 1 d . . .
O5 O 0.9419(3) 0.37000(14) 1.0429(2) 0.0672(9) Uani 1 1 d . . .
H5E H 0.9893 0.3992 1.0578 0.101 Uiso 1 1 calc R . .
O6 O 0.9058(2) 0.37753(11) 0.8370(2) 0.0551(8) Uani 1 1 d . . .
O7 O 0.2970(2) 0.07829(12) 0.7073(2) 0.0513(7) Uani 1 1 d . . .
O8 O 0.2521(2) -0.03409(11) 0.6872(2) 0.0509(7) Uani 1 1 d . . .
H8E H 0.1982 -0.0592 0.6654 0.076 Uiso 1 1 calc R . .
O9 O 0.0838(2) 0.04328(12) 0.6293(2) 0.0476(7) Uani 1 1 d . . .
N3 N 0.9651(3) -0.00223(16) 0.7745(3) 0.0528(9) Uani 1 1 d . . .
H3D H 1.0028 0.0181 0.7316 0.063 Uiso 1 1 calc R . .
N4 N 0.9604(3) -0.06478(16) 0.7823(3) 0.0502(9) Uani 1 1 d . . .
H4D H 0.9946 -0.0910 0.7454 0.060 Uiso 1 1 calc R . .
N1 N 0.5201(3) 0.08699(14) 0.9241(3) 0.0472(8) Uani 1 1 d . . .
H1D H 0.4785 0.1198 0.9329 0.057 Uiso 1 1 calc R . .
N2 N 0.4896(3) 0.04280(15) 0.8476(3) 0.0490(9) Uani 1 1 d . . .
H2D H 0.4241 0.0423 0.8001 0.059 Uiso 1 1 calc R . .
C17 C 0.6835(4) 0.11279(19) 1.0773(3) 0.0610(12) Uani 1 1 d . . .
H17A H 0.7438 0.1384 1.0543 0.092 Uiso 1 1 calc R . .
H17B H 0.7195 0.0869 1.1379 0.092 Uiso 1 1 calc R . .
H17C H 0.6240 0.1394 1.0994 0.092 Uiso 1 1 calc R . .
C16 C 0.6260(3) 0.07187(17) 0.9845(3) 0.0397(9) Uani 1 1 d . . .
C15 C 0.6649(3) 0.01664(16) 0.9436(3) 0.0357(9) Uani 1 1 d . . .
C14 C 0.5754(3) -0.00046(17) 0.8559(3) 0.0428(10) Uani 1 1 d . . .
C13 C 0.5662(4) -0.0552(2) 0.7807(3) 0.0599(12) Uani 1 1 d . . .
H13B H 0.4861 -0.0579 0.7393 0.090 Uiso 1 1 calc R . .
H13C H 0.5850 -0.0931 0.8225 0.090 Uiso 1 1 calc R . .
H13A H 0.6213 -0.0501 0.7316 0.090 Uiso 1 1 calc R . .
C18 C 0.7786(3) -0.01821(17) 0.9836(3) 0.0422(9) Uani 1 1 d . . .
H18B H 0.7594 -0.0599 1.0071 0.051 Uiso 1 1 calc R . .
H18A H 0.8233 0.0036 1.0468 0.051 Uiso 1 1 calc R . .
C19 C 0.8930(5) 0.09303(19) 0.8518(4) 0.0720(14) Uani 1 1 d . . .
H19C H 0.9570 0.1127 0.8237 0.108 Uiso 1 1 calc R . .
H19A H 0.8980 0.1046 0.9272 0.108 Uiso 1 1 calc R . .
H19B H 0.8177 0.1067 0.8101 0.108 Uiso 1 1 calc R . .
C20 C 0.9027(3) 0.02384(18) 0.8430(3) 0.0444(10) Uani 1 1 d . . .
C21 C 0.8565(3) -0.02461(17) 0.8983(3) 0.0377(9) Uani 1 1 d . . .
C22 C 0.8939(3) -0.08028(18) 0.8566(3) 0.0431(10) Uani 1 1 d . . .
C23 C 0.8709(4) -0.14782(18) 0.8803(4) 0.0646(13) Uani 1 1 d . . .
H23A H 0.9055 -0.1744 0.8321 0.097 Uiso 1 1 calc R . .
H23C H 0.7862 -0.1551 0.8692 0.097 Uiso 1 1 calc R . .
H23B H 0.9062 -0.1573 0.9549 0.097 Uiso 1 1 calc R . .
C1 C 0.3652(3) 0.28686(17) 0.9029(4) 0.0539(11) Uani 1 1 d . . .
H1B H 0.3321 0.3159 0.8449 0.065 Uiso 1 1 calc R . .
H1A H 0.3488 0.3037 0.9711 0.065 Uiso 1 1 calc R . .
C2 C 0.4984(3) 0.28351(16) 0.9102(3) 0.0444(10) Uani 1 1 d . . .
C7 C 0.5747(4) 0.28289(18) 1.0100(3) 0.0491(10) Uani 1 1 d . . .
H7 H 0.5435 0.2857 1.0738 0.059 Uiso 1 1 calc R . .
C6 C 0.6969(4) 0.27811(18) 1.0170(4) 0.0513(11) Uani 1 1 d . . .
H6 H 0.7466 0.2786 1.0856 0.062 Uiso 1 1 calc R . .
C5 C 0.7467(3) 0.27267(16) 0.9251(3) 0.0435(10) Uani 1 1 d . . .
C4 C 0.6702(4) 0.2745(2) 0.8242(4) 0.0598(12) Uani 1 1 d . . .
H4 H 0.7016 0.2719 0.7603 0.072 Uiso 1 1 calc R . .
C3 C 0.5477(4) 0.2801(2) 0.8173(4) 0.0579(12) Uani 1 1 d . . .
H3 H 0.4980 0.2817 0.7488 0.069 Uiso 1 1 calc R . .
C8 C 0.8792(3) 0.26573(17) 0.9323(4) 0.0542(11) Uani 1 1 d . . .
H8A H 0.8930 0.2409 0.8703 0.065 Uiso 1 1 calc R . .
H8B H 0.9113 0.2423 0.9983 0.065 Uiso 1 1 calc R . .
C9 C 0.2499(3) 0.03160(18) 0.5029(3) 0.0461(10) Uani 1 1 d . . .
H9A H 0.1984 0.0012 0.4588 0.055 Uiso 1 1 calc R . .
H9B H 0.2320 0.0727 0.4698 0.055 Uiso 1 1 calc R . .
C12 C 0.4112(4) -0.04409(18) 0.4699(3) 0.0480(10) Uani 1 1 d . . .
H12 H 0.3525 -0.0746 0.4498 0.058 Uiso 1 1 calc R . .
C10 C 0.3787(3) 0.01543(17) 0.5004(3) 0.0392(9) Uani 1 1 d . . .
C11 C 0.4703(4) 0.05855(18) 0.5309(3) 0.0467(10) Uani 1 1 d . . .
H11 H 0.4516 0.0986 0.5527 0.056 Uiso 1 1 calc R . .
O10 O 0.9677(9) 0.2224(4) 0.7076(8) 0.101(5) Uiso 0.395(10) 1 d P . .


_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
P3 O7 1.499(3) . ?
P3 O9 1.510(3) . ?
P3 O8 1.567(2) . ?
P3 C9 1.782(4) . ?
P2 O4 1.504(3) . ?
P2 O6 1.505(3) . ?
P2 O5 1.562(3) . ?
P2 C8 1.793(4) . ?
P1 O1 1.486(3) . ?
P1 O3 1.529(3) . ?
P1 O2 1.559(3) . ?
P1 C1 1.797(4) . ?
O2 H2E 0.8200 . ?
O3 H3E 0.8200 . ?
O5 H5E 0.8200 . ?
O8 H8E 0.8200 . ?
N3 C20 1.327(5) . ?
N3 N4 1.334(4) . ?
N3 H3D 0.8600 . ?
N4 C22 1.340(5) . ?
N4 H4D 0.8600 . ?
N1 C16 1.334(4) . ?
N1 N2 1.334(4) . ?
N1 H1D 0.8600 . ?
N2 C14 1.331(4) . ?
N2 H2D 0.8600 . ?
C17 C16 1.493(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 C15 1.384(5) . ?
C15 C14 1.393(5) . ?
C15 C18 1.492(5) . ?
C14 C13 1.483(5) . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 H13A 0.9600 . ?
C18 C21 1.510(5) . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C19 C20 1.479(5) . ?
C19 H19C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C20 C21 1.393(5) . ?
C21 C22 1.389(5) . ?
C22 C23 1.497(5) . ?
C23 H23A 0.9600 . ?
C23 H23C 0.9600 . ?
C23 H23B 0.9600 . ?
C1 C2 1.502(5) . ?
C1 H1B 0.9700 . ?
C1 H1A 0.9700 . ?
C2 C7 1.375(5) . ?
C2 C3 1.375(5) . ?
C7 C6 1.381(5) . ?
C7 H7 0.9300 . ?
C6 C5 1.371(5) . ?
C6 H6 0.9300 . ?
C5 C4 1.387(6) . ?
C5 C8 1.501(5) . ?
C4 C3 1.386(5) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.512(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 C11 1.385(5) 3_656 ?
C12 C10 1.389(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.386(5) . ?
C11 C12 1.385(5) 3_656 ?
C11 H11 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
O7 P3 O9 115.82(15) . . ?
O7 P3 O8 105.67(15) . . ?
O9 P3 O8 110.24(14) . . ?
O7 P3 C9 109.58(17) . . ?
O9 P3 C9 109.05(16) . . ?
O8 P3 C9 106.01(17) . . ?
O4 P2 O6 112.53(18) . . ?
O4 P2 O5 111.37(18) . . ?
O6 P2 O5 110.40(17) . . ?
O4 P2 C8 109.66(16) . . ?
O6 P2 C8 109.27(18) . . ?
O5 P2 C8 103.19(19) . . ?
O1 P1 O3 112.96(17) . . ?
O1 P1 O2 112.27(15) . . ?
O3 P1 O2 108.43(19) . . ?
O1 P1 C1 111.17(18) . . ?
O3 P1 C1 107.43(17) . . ?
O2 P1 C1 104.10(19) . . ?
P1 O2 H2E 109.5 . . ?
P1 O3 H3E 109.5 . . ?
P2 O5 H5E 109.5 . . ?
P3 O8 H8E 109.5 . . ?
C20 N3 N4 109.6(3) . . ?
C20 N3 H3D 125.2 . . ?
N4 N3 H3D 125.2 . . ?
N3 N4 C22 109.3(3) . . ?
N3 N4 H4D 125.4 . . ?
C22 N4 H4D 125.4 . . ?
C16 N1 N2 108.6(3) . . ?
C16 N1 H1D 125.7 . . ?
N2 N1 H1D 125.7 . . ?
C14 N2 N1 109.9(3) . . ?
C14 N2 H2D 125.0 . . ?
N1 N2 H2D 125.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C16 C15 108.3(3) . . ?
N1 C16 C17 120.9(3) . . ?
C15 C16 C17 130.8(4) . . ?
C16 C15 C14 105.7(3) . . ?
C16 C15 C18 127.9(3) . . ?
C14 C15 C18 126.3(3) . . ?
N2 C14 C15 107.4(3) . . ?
N2 C14 C13 121.9(4) . . ?
C15 C14 C13 130.8(3) . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
C15 C18 C21 113.4(3) . . ?
C15 C18 H18B 108.9 . . ?
C21 C18 H18B 108.9 . . ?
C15 C18 H18A 108.9 . . ?
C21 C18 H18A 108.9 . . ?
H18B C18 H18A 107.7 . . ?
C20 C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C20 C21 107.7(3) . . ?
N3 C20 C19 121.2(4) . . ?
C21 C20 C19 131.1(4) . . ?
C22 C21 C20 106.0(3) . . ?
C22 C21 C18 126.8(3) . . ?
C20 C21 C18 127.2(3) . . ?
N4 C22 C21 107.4(3) . . ?
N4 C22 C23 120.9(4) . . ?
C21 C22 C23 131.7(4) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23C C23 H23B 109.5 . . ?
C2 C1 P1 113.9(3) . . ?
C2 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
C2 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
H1B C1 H1A 107.7 . . ?
C7 C2 C3 117.9(4) . . ?
C7 C2 C1 120.9(4) . . ?
C3 C2 C1 121.1(4) . . ?
C2 C7 C6 121.1(4) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C5 C6 C7 121.4(4) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C5 C4 117.7(4) . . ?
C6 C5 C8 121.7(4) . . ?
C4 C5 C8 120.6(4) . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C8 P2 115.4(3) . . ?
C5 C8 H8A 108.4 . . ?
P2 C8 H8A 108.4 . . ?
C5 C8 H8B 108.4 . . ?
P2 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 P3 113.6(3) . . ?
C10 C9 H9A 108.9 . . ?
P3 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
P3 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C12 C10 120.8(3) 3_656 . ?
C11 C12 H12 119.6 3_656 . ?
C10 C12 H12 119.6 . . ?
C11 C10 C12 116.8(3) . . ?
C11 C10 C9 121.8(3) . . ?
C12 C10 C9 121.4(3) . . ?
C12 C11 C10 122.4(4) 3_656 . ?
C12 C11 H11 118.8 3_656 . ?
C10 C11 H11 118.8 . . ?

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
C20 N3 N4 C22 0.2(4) . . . . ?
C16 N1 N2 C14 -1.3(4) . . . . ?
N2 N1 C16 C15 1.1(4) . . . . ?
N2 N1 C16 C17 -179.9(3) . . . . ?
N1 C16 C15 C14 -0.5(4) . . . . ?
C17 C16 C15 C14 -179.4(4) . . . . ?
N1 C16 C15 C18 179.5(3) . . . . ?
C17 C16 C15 C18 0.6(6) . . . . ?
N1 N2 C14 C15 0.9(4) . . . . ?
N1 N2 C14 C13 -179.6(4) . . . . ?
C16 C15 C14 N2 -0.2(4) . . . . ?
C18 C15 C14 N2 179.8(3) . . . . ?
C16 C15 C14 C13 -179.7(4) . . . . ?
C18 C15 C14 C13 0.3(7) . . . . ?
C16 C15 C18 C21 -119.9(4) . . . . ?
C14 C15 C18 C21 60.1(5) . . . . ?
N4 N3 C20 C21 0.5(4) . . . . ?
N4 N3 C20 C19 179.8(4) . . . . ?
N3 C20 C21 C22 -1.0(4) . . . . ?
C19 C20 C21 C22 179.9(4) . . . . ?
N3 C20 C21 C18 -179.3(3) . . . . ?
C19 C20 C21 C18 1.6(7) . . . . ?
C15 C18 C21 C22 -119.9(4) . . . . ?
C15 C18 C21 C20 58.0(5) . . . . ?
N3 N4 C22 C21 -0.8(4) . . . . ?
N3 N4 C22 C23 178.6(3) . . . . ?
C20 C21 C22 N4 1.1(4) . . . . ?
C18 C21 C22 N4 179.4(3) . . . . ?
C20 C21 C22 C23 -178.2(4) . . . . ?
C18 C21 C22 C23 0.1(7) . . . . ?
O1 P1 C1 C2 49.9(4) . . . . ?
O3 P1 C1 C2 174.0(3) . . . . ?
O2 P1 C1 C2 -71.1(3) . . . . ?
P1 C1 C2 C7 -100.5(4) . . . . ?
P1 C1 C2 C3 78.7(4) . . . . ?
C3 C2 C7 C6 -0.9(6) . . . . ?
C1 C2 C7 C6 178.2(3) . . . . ?
C2 C7 C6 C5 -1.2(6) . . . . ?
C7 C6 C5 C4 2.4(6) . . . . ?
C7 C6 C5 C8 -178.4(3) . . . . ?
C6 C5 C4 C3 -1.5(6) . . . . ?
C8 C5 C4 C3 179.2(4) . . . . ?
C7 C2 C3 C4 1.8(6) . . . . ?
C1 C2 C3 C4 -177.4(4) . . . . ?
C5 C4 C3 C2 -0.6(6) . . . . ?
C6 C5 C8 P2 -88.9(4) . . . . ?
C4 C5 C8 P2 90.4(4) . . . . ?
O4 P2 C8 C5 -177.4(3) . . . . ?
O6 P2 C8 C5 -53.6(4) . . . . ?
O5 P2 C8 C5 63.8(4) . . . . ?
O7 P3 C9 C10 57.3(3) . . . . ?
O9 P3 C9 C10 -175.0(3) . . . . ?
O8 P3 C9 C10 -56.3(3) . . . . ?
C11 C12 C10 C11 -0.9(6) 3_656 . . . ?
C11 C12 C10 C9 -179.3(3) 3_656 . . . ?
P3 C9 C10 C11 -75.7(4) . . . . ?
P3 C9 C10 C12 102.7(4) . . . . ?
C12 C10 C11 C12 0.9(6) . . . 3_656 ?
C9 C10 C11 C12 179.3(3) . . . 3_656 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 980596'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_EA_MBPz_squeezed

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N4, C2 H6 O7 P2, C2 H6 O'
_chemical_formula_sum            'C15 H30 N4 O8 P2'
_chemical_formula_weight         456.37

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.4912(9)
_cell_length_b                   9.4729(7)
_cell_length_c                   22.7526(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.245(4)
_cell_angle_gamma                90.00
_cell_volume                     2181.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    113
_cell_measurement_theta_min      2.01
_cell_measurement_theta_max      26.41

_exptl_crystal_description       cubic
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968.0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31105
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.41
_reflns_number_total             4462
_reflns_number_gt                3116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SAINT'
_computing_publication_material  'Bruker SAINT'

_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. 

_platon_squeeze_details

The segment of partial solvent electron densities was overruled by the SQUEEZE
 program in PLATON as the attempt of modeling the solvent molecule was ineffectual;
hence, the electron density was removed by SQUEEZE routine in PLATON to remove the
solvent molecule.A sum total of 28 electrons were accounted for in void
space of 202 A^3 which corresponds to an ethanol molecule.
 
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000 -0.032  0.000       202        56 ' '
   2  0.000 -0.012  0.500       202        56 ' '
;

_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)+(0.0978P)²+8.8120P] where P=(Fo²+2Fc²)/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_number_reflns         4462
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2439
_refine_ls_wR_factor_gt          0.2319
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N1 N 1.1122(4) 0.4272(5) 0.2027(2) 0.0421(11) Uani 1 1 d . . .
H1D H 1.1912 0.4602 0.2238 0.051 Uiso 1 1 calc R . .
N2 N 1.0809(4) 0.2903(5) 0.1906(2) 0.0410(11) Uani 1 1 d . . .
H2D H 1.1362 0.2216 0.2021 0.049 Uiso 1 1 calc R . .
N3 N 0.5979(4) 0.5437(5) -0.0599(2) 0.0378(10) Uani 1 1 d . . .
H3D H 0.5668 0.5251 -0.1017 0.045 Uiso 1 1 calc R . .
N4 N 0.5974(4) 0.6706(5) -0.0345(2) 0.0371(10) Uani 1 1 d . . .
H4D H 0.5655 0.7466 -0.0572 0.044 Uiso 1 1 calc R . .
C3 C 0.8871(7) 0.1367(7) 0.1398(4) 0.0588(17) Uani 1 1 d . . .
H3A H 0.9453 0.0679 0.1707 0.088 Uiso 1 1 calc R . .
H3B H 0.8704 0.1127 0.0955 0.088 Uiso 1 1 calc R . .
H3C H 0.8053 0.1379 0.1415 0.088 Uiso 1 1 calc R . .
C4 C 0.9495(5) 0.2781(6) 0.1577(3) 0.0373(12) Uani 1 1 d . . .
C5 C 0.8958(5) 0.4144(6) 0.1482(2) 0.0351(12) Uani 1 1 d . . .
C6 C 1.0019(5) 0.5046(6) 0.1769(2) 0.0351(12) Uani 1 1 d . . .
C7 C 1.0052(6) 0.6618(7) 0.1825(3) 0.0588(18) Uani 1 1 d . . .
H7A H 0.9889 0.7027 0.1407 0.088 Uiso 1 1 calc R . .
H7B H 1.0904 0.6912 0.2167 0.088 Uiso 1 1 calc R . .
H7C H 0.9383 0.6925 0.1935 0.088 Uiso 1 1 calc R . .
C8 C 0.7519(5) 0.4547(6) 0.1181(2) 0.0353(12) Uani 1 1 d . . .
H8A H 0.7417 0.5206 0.1479 0.042 Uiso 1 1 calc R . .
H8B H 0.7015 0.3708 0.1157 0.042 Uiso 1 1 calc R . .
C9 C 0.6688(6) 0.2983(6) -0.0222(3) 0.0478(14) Uani 1 1 d . . .
H9A H 0.7542 0.2828 -0.0190 0.072 Uiso 1 1 calc R . .
H9B H 0.6014 0.2724 -0.0660 0.072 Uiso 1 1 calc R . .
H9C H 0.6602 0.2417 0.0106 0.072 Uiso 1 1 calc R . .
C10 C 0.6544(5) 0.4492(6) -0.0101(3) 0.0350(11) Uani 1 1 d . . .
C11 C 0.6925(5) 0.5205(5) 0.0493(2) 0.0312(11) Uani 1 1 d . . .
C12 C 0.6547(5) 0.6598(6) 0.0315(3) 0.0366(12) Uani 1 1 d . . .
P1 P 0.56048(12) 0.09834(12) 0.18459(6) 0.0277(3) Uani 1 1 d . . .
P2 P 0.39909(12) 0.09303(12) 0.26538(6) 0.0263(3) Uani 1 1 d . . .
O1 O 0.5333(4) 0.1267(4) 0.11451(19) 0.0446(10) Uani 1 1 d . . .
O2 O 0.6269(3) -0.0398(3) 0.21440(18) 0.0347(8) Uani 1 1 d . . .
O3 O 0.6528(3) 0.2142(4) 0.23428(19) 0.0414(9) Uani 1 1 d . . .
H3E H 0.6137 0.2900 0.2257 0.062 Uiso 1 1 d R . .
O4 O 0.2576(3) 0.1032(4) 0.25050(18) 0.0373(9) Uani 1 1 d . . .
O5 O 0.4832(4) 0.2191(3) 0.30964(17) 0.0358(8) Uani 1 1 d . . .
H5E H 0.4407 0.2925 0.2966 0.054 Uiso 1 1 d R . .
O6 O 0.4678(3) -0.0401(3) 0.30160(16) 0.0321(8) Uani 1 1 d . . .
O7 O 0.3442(3) 0.2474(3) 0.15891(17) 0.0284(8) Uani 1 1 d . . .
H7Z H 0.3950 0.3094 0.1821 0.043 Uiso 1 1 calc R . .
C1 C 0.3047(5) 0.0019(5) 0.1359(3) 0.0356(12) Uani 1 1 d . . .
H1A H 0.2164 0.0226 0.1276 0.053 Uiso 1 1 calc R . .
H1B H 0.3289 -0.0912 0.1544 0.053 Uiso 1 1 calc R . .
H1C H 0.3087 0.0068 0.0947 0.053 Uiso 1 1 calc R . .
C2 C 0.4007(4) 0.1101(4) 0.1854(2) 0.0246(9) Uani 1 1 d . . .
C13 C 0.6695(6) 0.7871(7) 0.0724(3) 0.0552(16) Uani 1 1 d . . .
H13A H 0.7500 0.8349 0.0815 0.083 Uiso 1 1 calc R . .
H13B H 0.6722 0.7596 0.1136 0.083 Uiso 1 1 calc R . .
H13C H 0.5959 0.8491 0.0484 0.083 Uiso 1 1 calc R . .


_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
N1 C6 1.336(6) . ?
N1 N2 1.339(6) . ?
N1 H1D 0.8600 . ?
N2 C4 1.336(7) . ?
N2 H2D 0.8600 . ?
N3 N4 1.335(6) . ?
N3 C10 1.346(7) . ?
N3 H3D 0.8600 . ?
N4 C12 1.329(7) . ?
N4 H4D 0.8600 . ?
C3 C4 1.482(8) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.403(7) . ?
C5 C6 1.375(7) . ?
C5 C8 1.508(7) . ?
C6 C7 1.494(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C11 1.513(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.480(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.383(7) . ?
C11 C12 1.389(7) . ?
C12 C13 1.482(8) . ?
P1 O1 1.497(4) . ?
P1 O2 1.505(3) . ?
P1 O3 1.572(4) . ?
P1 C2 1.848(5) . ?
P2 O4 1.498(4) . ?
P2 O6 1.509(3) . ?
P2 O5 1.566(4) . ?
P2 C2 1.837(5) . ?
O3 H3E 0.8200 . ?
O5 H5E 0.8201 . ?
O7 C2 1.450(5) . ?
O7 H7Z 0.8200 . ?
C1 C2 1.536(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C6 N1 N2 109.5(4) . . ?
C6 N1 H1D 125.3 . . ?
N2 N1 H1D 125.3 . . ?
C4 N2 N1 108.8(4) . . ?
C4 N2 H2D 125.6 . . ?
N1 N2 H2D 125.6 . . ?
N4 N3 C10 109.5(4) . . ?
N4 N3 H3D 125.3 . . ?
C10 N3 H3D 125.3 . . ?
C12 N4 N3 108.6(4) . . ?
C12 N4 H4D 125.7 . . ?
N3 N4 H4D 125.7 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 107.7(5) . . ?
N2 C4 C3 120.2(5) . . ?
C5 C4 C3 132.0(5) . . ?
C6 C5 C4 105.8(4) . . ?
C6 C5 C8 126.4(5) . . ?
C4 C5 C8 127.7(5) . . ?
N1 C6 C5 108.2(5) . . ?
N1 C6 C7 122.0(5) . . ?
C5 C6 C7 129.9(5) . . ?
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 . . ?
C5 C8 C11 115.8(4) . . ?
C5 C8 H8A 108.3 . . ?
C11 C8 H8A 108.3 . . ?
C5 C8 H8B 108.3 . . ?
C11 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 107.6(5) . . ?
N3 C10 C9 122.5(5) . . ?
C11 C10 C9 129.9(5) . . ?
C10 C11 C12 105.6(4) . . ?
C10 C11 C8 126.0(5) . . ?
C12 C11 C8 128.2(5) . . ?
N4 C12 C11 108.8(5) . . ?
N4 C12 C13 119.7(5) . . ?
C11 C12 C13 131.5(5) . . ?
O1 P1 O2 116.2(2) . . ?
O1 P1 O3 111.7(2) . . ?
O2 P1 O3 104.9(2) . . ?
O1 P1 C2 107.0(2) . . ?
O2 P1 C2 110.0(2) . . ?
O3 P1 C2 106.6(2) . . ?
O4 P2 O6 114.1(2) . . ?
O4 P2 O5 111.7(2) . . ?
O6 P2 O5 106.36(19) . . ?
O4 P2 C2 106.8(2) . . ?
O6 P2 C2 111.5(2) . . ?
O5 P2 C2 106.1(2) . . ?
P1 O3 H3E 109.5 . . ?
P2 O5 H5E 109.5 . . ?
C2 O7 H7Z 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O7 C2 C1 105.6(3) . . ?
O7 C2 P2 106.1(3) . . ?
C1 C2 P2 109.1(3) . . ?
O7 C2 P1 107.6(3) . . ?
C1 C2 P1 109.0(3) . . ?
P2 C2 P1 118.7(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C6 N1 N2 C4 -1.0(6) . . . . ?
C10 N3 N4 C12 0.7(6) . . . . ?
N1 N2 C4 C5 0.5(6) . . . . ?
N1 N2 C4 C3 -178.0(5) . . . . ?
N2 C4 C5 C6 0.1(6) . . . . ?
C3 C4 C5 C6 178.4(6) . . . . ?
N2 C4 C5 C8 -175.2(5) . . . . ?
C3 C4 C5 C8 3.1(10) . . . . ?
N2 N1 C6 C5 1.0(6) . . . . ?
N2 N1 C6 C7 180.0(5) . . . . ?
C4 C5 C6 N1 -0.7(6) . . . . ?
C8 C5 C6 N1 174.7(5) . . . . ?
C4 C5 C6 C7 -179.5(6) . . . . ?
C8 C5 C6 C7 -4.1(9) . . . . ?
C6 C5 C8 C11 77.4(7) . . . . ?
C4 C5 C8 C11 -108.2(6) . . . . ?
N4 N3 C10 C11 -0.7(6) . . . . ?
N4 N3 C10 C9 179.5(5) . . . . ?
N3 C10 C11 C12 0.4(6) . . . . ?
C9 C10 C11 C12 -179.8(6) . . . . ?
N3 C10 C11 C8 175.6(5) . . . . ?
C9 C10 C11 C8 -4.6(9) . . . . ?
C5 C8 C11 C10 77.0(7) . . . . ?
C5 C8 C11 C12 -108.9(6) . . . . ?
N3 N4 C12 C11 -0.4(6) . . . . ?
N3 N4 C12 C13 178.8(5) . . . . ?
C10 C11 C12 N4 0.0(6) . . . . ?
C8 C11 C12 N4 -175.0(5) . . . . ?
C10 C11 C12 C13 -179.1(6) . . . . ?
C8 C11 C12 C13 5.8(9) . . . . ?
O4 P2 C2 O7 60.3(3) . . . . ?
O6 P2 C2 O7 -174.4(3) . . . . ?
O5 P2 C2 O7 -59.0(3) . . . . ?
O4 P2 C2 C1 -53.1(3) . . . . ?
O6 P2 C2 C1 72.2(3) . . . . ?
O5 P2 C2 C1 -172.4(3) . . . . ?
O4 P2 C2 P1 -178.6(2) . . . . ?
O6 P2 C2 P1 -53.3(3) . . . . ?
O5 P2 C2 P1 62.1(3) . . . . ?
O1 P1 C2 O7 -55.4(3) . . . . ?
O2 P1 C2 O7 177.5(3) . . . . ?
O3 P1 C2 O7 64.3(3) . . . . ?
O1 P1 C2 C1 58.6(4) . . . . ?
O2 P1 C2 C1 -68.5(4) . . . . ?
O3 P1 C2 C1 178.3(3) . . . . ?
O1 P1 C2 P2 -175.8(2) . . . . ?
O2 P1 C2 P2 57.1(3) . . . . ?
O3 P1 C2 P2 -56.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.41
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 980597'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1889shi_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 N4, C11 H16 N4, C2 H4 O5 P, C H4 O'
_chemical_formula_sum            'C25 H41 N8 O6 P'
_chemical_formula_weight         580.63

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 c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   15.269(3)
_cell_length_b                   8.820(2)
_cell_length_c                   21.635(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2913.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    137
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      28.46

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240.0
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47141
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         28.46
_reflns_number_total             7288
_reflns_number_gt                5425
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker kappa Apex'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SAINT'
_computing_publication_material  'Bruker SAINT'

_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)+(0.1000P)²+0.4865P] where P=(Fo²+2Fc²)/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   0.35(12)
_refine_ls_number_reflns         7288
_refine_ls_number_parameters     374
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1532
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.001
_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
P1 P 0.51307(5) 0.77674(8) 0.93439(4) 0.01688(17) Uani 1 1 d . . .
C22 C 0.2029(2) 1.0075(3) 0.64834(13) 0.0151(6) Uani 1 1 d . . .
C11 C 0.7059(2) 0.4798(3) 0.72248(14) 0.0173(6) Uani 1 1 d . . .
C5 C 0.8432(2) 0.4886(3) 0.65834(14) 0.0156(6) Uani 1 1 d . . .
C17 C 0.3478(2) 0.9923(3) 0.77563(14) 0.0172(6) Uani 1 1 d . . .
C20 C 0.1216(2) 0.9164(4) 0.74768(14) 0.0201(6) Uani 1 1 d . . .
H20A H 0.1631 0.8485 0.7662 0.030 Uiso 1 1 calc R . .
H20B H 0.0633 0.8801 0.7551 0.030 Uiso 1 1 calc R . .
H20C H 0.1281 1.0156 0.7654 0.030 Uiso 1 1 calc R . .
C19 C 0.27403(19) 1.1033(3) 0.67634(13) 0.0160(6) Uani 1 1 d . . .
H19A H 0.2476 1.1771 0.7038 0.019 Uiso 1 1 calc R . .
H19B H 0.3036 1.1584 0.6436 0.019 Uiso 1 1 calc R . .
C16 C 0.3407(2) 1.0131(3) 0.71190(14) 0.0164(6) Uani 1 1 d . . .
C13 C 0.6217(2) 0.5940(4) 0.62919(15) 0.0227(7) Uani 1 1 d . . .
H13A H 0.6642 0.6620 0.6119 0.034 Uiso 1 1 calc R . .
H13B H 0.5642 0.6365 0.6246 0.034 Uiso 1 1 calc R . .
H13C H 0.6244 0.4984 0.6081 0.034 Uiso 1 1 calc R . .
C15 C 0.4058(2) 0.9219(3) 0.68645(15) 0.0161(6) Uani 1 1 d . . .
C7 C 0.9223(2) 0.5974(3) 0.75604(14) 0.0203(7) Uani 1 1 d . . .
H7A H 0.8795 0.6642 0.7737 0.030 Uiso 1 1 calc R . .
H7B H 0.9797 0.6396 0.7618 0.030 Uiso 1 1 calc R . .
H7C H 0.9191 0.5004 0.7760 0.030 Uiso 1 1 calc R . .
C8 C 0.7745(2) 0.3909(3) 0.68895(15) 0.0181(6) Uani 1 1 d . . .
H8A H 0.7464 0.3290 0.6577 0.022 Uiso 1 1 calc R . .
H8B H 0.8031 0.3233 0.7180 0.022 Uiso 1 1 calc R . .
C6 C 0.9049(2) 0.5791(3) 0.68895(14) 0.0144(6) Uani 1 1 d . . .
C23 C 0.1879(2) 0.9762(3) 0.58665(14) 0.0175(6) Uani 1 1 d . . .
C21 C 0.1375(2) 0.9245(3) 0.68023(14) 0.0166(6) Uani 1 1 d . . .
C12 C 0.6405(2) 0.5709(3) 0.69560(14) 0.0159(6) Uani 1 1 d . . .
C4 C 0.8554(2) 0.5142(3) 0.59575(14) 0.0180(6) Uani 1 1 d . . .
C10 C 0.6937(2) 0.4944(3) 0.78539(14) 0.0170(6) Uani 1 1 d . . .
C14 C 0.4304(2) 0.8961(3) 0.62129(14) 0.0199(7) Uani 1 1 d . . .
H14A H 0.3968 0.8134 0.6049 0.030 Uiso 1 1 calc R . .
H14B H 0.4917 0.8719 0.6189 0.030 Uiso 1 1 calc R . .
H14C H 0.4189 0.9861 0.5977 0.030 Uiso 1 1 calc R . .
C2 C 0.5599(2) 1.0808(3) 0.92704(15) 0.0223(7) Uani 1 1 d . . .
C24 C 0.2327(2) 1.0296(4) 0.52934(14) 0.0228(7) Uani 1 1 d . . .
H24A H 0.1928 1.0235 0.4951 0.034 Uiso 1 1 calc R . .
H24B H 0.2828 0.9668 0.5213 0.034 Uiso 1 1 calc R . .
H24C H 0.2512 1.1327 0.5347 0.034 Uiso 1 1 calc R . .
C3 C 0.8133(2) 0.4490(4) 0.53977(14) 0.0216(7) Uani 1 1 d . . .
H3A H 0.8552 0.3893 0.5174 0.032 Uiso 1 1 calc R . .
H3B H 0.7924 0.5296 0.5138 0.032 Uiso 1 1 calc R . .
H3C H 0.7650 0.3860 0.5519 0.032 Uiso 1 1 calc R . .
C9 C 0.7396(2) 0.4243(4) 0.83980(15) 0.0249(7) Uani 1 1 d . . .
H9A H 0.6970 0.3908 0.8694 0.037 Uiso 1 1 calc R . .
H9B H 0.7774 0.4981 0.8586 0.037 Uiso 1 1 calc R . .
H9C H 0.7738 0.3393 0.8261 0.037 Uiso 1 1 calc R . .
C18 C 0.2983(2) 1.0680(4) 0.82710(14) 0.0212(7) Uani 1 1 d . . .
H18A H 0.3387 1.1208 0.8534 0.032 Uiso 1 1 calc R . .
H18B H 0.2676 0.9928 0.8507 0.032 Uiso 1 1 calc R . .
H18C H 0.2571 1.1387 0.8100 0.032 Uiso 1 1 calc R . .
C1 C 0.5891(2) 0.9236(3) 0.91191(16) 0.0232(7) Uani 1 1 d . . .
H1A H 0.6447 0.9050 0.9322 0.028 Uiso 1 1 calc R . .
H1B H 0.5987 0.9168 0.8677 0.028 Uiso 1 1 calc R . .
O4 O 0.51560(18) 1.1440(3) 0.88159(10) 0.0310(6) Uani 1 1 d . . .
H4Z H 0.4856 1.2135 0.8953 0.046 Uiso 1 1 calc R . .
O1 O 0.42247(14) 0.8243(2) 0.90744(10) 0.0227(5) Uani 1 1 d . . .
H1E H 0.4247 0.8228 0.8696 0.034 Uiso 1 1 calc R . .
O3 O 0.50297(15) 0.7734(3) 1.00339(11) 0.0239(5) Uani 1 1 d . . .
O2 O 0.54772(16) 0.6334(2) 0.90623(10) 0.0264(5) Uani 1 1 d . . .
O5 O 0.57504(19) 1.1433(3) 0.97570(12) 0.0420(7) Uani 1 1 d . . .
N1 N 0.95100(18) 0.6536(3) 0.64621(11) 0.0166(5) Uani 1 1 d . . .
H1D H 0.9928 0.7164 0.6536 0.020 Uiso 1 1 calc R . .
N7 N 0.08726(17) 0.8478(3) 0.64050(12) 0.0176(5) Uani 1 1 d . . .
N4 N 0.59090(17) 0.6374(3) 0.73883(12) 0.0185(6) Uani 1 1 d . . .
N2 N 0.92153(17) 0.6146(3) 0.58963(12) 0.0168(5) Uani 1 1 d . . .
H2D H 0.9417 0.6483 0.5551 0.020 Uiso 1 1 calc R . .
N3 N 0.62523(17) 0.5893(3) 0.79328(12) 0.0187(6) Uani 1 1 d . . .
H3D H 0.6056 0.6163 0.8289 0.022 Uiso 1 1 calc R . .
N5 N 0.44510(17) 0.8515(3) 0.73406(11) 0.0156(5) Uani 1 1 d . . .
H5D H 0.4872 0.7875 0.7299 0.019 Uiso 1 1 calc R . .
N8 N 0.11973(17) 0.8805(3) 0.58371(12) 0.0180(5) Uani 1 1 d . . .
H8D H 0.0991 0.8441 0.5498 0.022 Uiso 1 1 calc R . .
N6 N 0.41070(18) 0.8932(3) 0.78941(12) 0.0178(5) Uani 1 1 d . . .
O6 O 0.44179(18) 0.3975(3) 0.90867(12) 0.0326(6) Uani 1 1 d . . .
H6C H 0.4833 0.4563 0.9075 0.049 Uiso 1 1 calc R . .
C25 C 0.4054(3) 0.3968(5) 0.9691(2) 0.0471(11) Uani 1 1 d . . .
H25A H 0.4506 0.3750 0.9986 0.071 Uiso 1 1 calc R . .
H25B H 0.3606 0.3207 0.9716 0.071 Uiso 1 1 calc R . .
H25C H 0.3805 0.4944 0.9778 0.071 Uiso 1 1 calc R . .


_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
P1 O2 1.500(2) . ?
P1 O3 1.501(2) . ?
P1 O1 1.559(2) . ?
P1 C1 1.805(3) . ?
C22 C23 1.382(4) . ?
C22 C21 1.418(4) . ?
C22 C19 1.503(4) . ?
C11 C10 1.380(4) . ?
C11 C12 1.407(4) . ?
C11 C8 1.496(4) . ?
C5 C4 1.385(4) . ?
C5 C6 1.401(4) . ?
C5 C8 1.510(4) . ?
C17 N6 1.333(4) . ?
C17 C16 1.395(4) . ?
C17 C18 1.502(4) . ?
C20 C21 1.481(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 C16 1.504(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 C15 1.392(4) . ?
C13 C12 1.479(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 N5 1.344(4) . ?
C15 C14 1.477(4) . ?
C7 C6 1.485(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 N1 1.335(4) . ?
C23 N8 1.342(4) . ?
C23 C24 1.492(4) . ?
C21 N7 1.336(4) . ?
C12 N4 1.339(4) . ?
C4 N2 1.349(4) . ?
C4 C3 1.487(4) . ?
C10 N3 1.350(4) . ?
C10 C9 1.503(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C2 O5 1.210(4) . ?
C2 O4 1.317(4) . ?
C2 C1 1.493(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O4 H4Z 0.8200 . ?
O1 H1E 0.8200 . ?
N1 N2 1.349(4) . ?
N1 H1D 0.8600 . ?
N7 N8 1.356(4) . ?
N4 N3 1.357(4) . ?
N2 H2D 0.8600 . ?
N3 H3D 0.8600 . ?
N5 N6 1.358(3) . ?
N5 H5D 0.8600 . ?
N8 H8D 0.8600 . ?
O6 C25 1.420(5) . ?
O6 H6C 0.8200 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
O2 P1 O3 115.08(13) . . ?
O2 P1 O1 112.83(14) . . ?
O3 P1 O1 106.62(13) . . ?
O2 P1 C1 105.58(14) . . ?
O3 P1 C1 110.36(15) . . ?
O1 P1 C1 106.04(14) . . ?
C23 C22 C21 104.5(3) . . ?
C23 C22 C19 128.4(3) . . ?
C21 C22 C19 127.1(3) . . ?
C10 C11 C12 105.0(3) . . ?
C10 C11 C8 128.4(3) . . ?
C12 C11 C8 126.6(3) . . ?
C4 C5 C6 106.2(3) . . ?
C4 C5 C8 128.0(3) . . ?
C6 C5 C8 125.8(3) . . ?
N6 C17 C16 111.3(3) . . ?
N6 C17 C18 119.2(3) . . ?
C16 C17 C18 129.4(3) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C19 C16 113.5(2) . . ?
C22 C19 H19A 108.9 . . ?
C16 C19 H19A 108.9 . . ?
C22 C19 H19B 108.9 . . ?
C16 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C15 C16 C17 105.1(3) . . ?
C15 C16 C19 125.9(3) . . ?
C17 C16 C19 128.9(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C15 C16 106.4(3) . . ?
N5 C15 C14 123.1(3) . . ?
C16 C15 C14 130.4(3) . . ?
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 . . ?
C11 C8 C5 113.6(2) . . ?
C11 C8 H8A 108.8 . . ?
C5 C8 H8A 108.8 . . ?
C11 C8 H8B 108.8 . . ?
C5 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N1 C6 C5 107.9(3) . . ?
N1 C6 C7 121.9(3) . . ?
C5 C6 C7 130.2(3) . . ?
N8 C23 C22 107.5(3) . . ?
N8 C23 C24 121.0(3) . . ?
C22 C23 C24 131.6(3) . . ?
N7 C21 C22 110.7(3) . . ?
N7 C21 C20 121.1(3) . . ?
C22 C21 C20 128.3(3) . . ?
N4 C12 C11 111.3(3) . . ?
N4 C12 C13 120.5(3) . . ?
C11 C12 C13 128.2(3) . . ?
N2 C4 C5 107.7(3) . . ?
N2 C4 C3 119.9(3) . . ?
C5 C4 C3 132.4(3) . . ?
N3 C10 C11 106.7(3) . . ?
N3 C10 C9 121.2(3) . . ?
C11 C10 C9 132.1(3) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C2 O4 123.7(3) . . ?
O5 C2 C1 123.8(3) . . ?
O4 C2 C1 112.5(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C1 P1 114.6(2) . . ?
C2 C1 H1A 108.6 . . ?
P1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
P1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C2 O4 H4Z 109.5 . . ?
P1 O1 H1E 109.5 . . ?
C6 N1 N2 109.1(3) . . ?
C6 N1 H1D 125.5 . . ?
N2 N1 H1D 125.5 . . ?
C21 N7 N8 105.4(2) . . ?
C12 N4 N3 104.5(2) . . ?
N1 N2 C4 109.1(3) . . ?
N1 N2 H2D 125.4 . . ?
C4 N2 H2D 125.4 . . ?
C10 N3 N4 112.5(2) . . ?
C10 N3 H3D 123.7 . . ?
N4 N3 H3D 123.7 . . ?
C15 N5 N6 112.2(3) . . ?
C15 N5 H5D 123.9 . . ?
N6 N5 H5D 123.9 . . ?
C23 N8 N7 112.0(3) . . ?
C23 N8 H8D 124.0 . . ?
N7 N8 H8D 124.0 . . ?
C17 N6 N5 105.0(2) . . ?
C25 O6 H6C 109.5 . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C23 C22 C19 C16 -110.6(3) . . . . ?
C21 C22 C19 C16 67.0(4) . . . . ?
N6 C17 C16 C15 -1.4(3) . . . . ?
C18 C17 C16 C15 176.1(3) . . . . ?
N6 C17 C16 C19 174.1(3) . . . . ?
C18 C17 C16 C19 -8.4(5) . . . . ?
C22 C19 C16 C15 74.2(4) . . . . ?
C22 C19 C16 C17 -100.5(3) . . . . ?
C17 C16 C15 N5 1.4(3) . . . . ?
C19 C16 C15 N5 -174.2(3) . . . . ?
C17 C16 C15 C14 179.9(3) . . . . ?
C19 C16 C15 C14 4.2(5) . . . . ?
C10 C11 C8 C5 -108.2(4) . . . . ?
C12 C11 C8 C5 69.9(4) . . . . ?
C4 C5 C8 C11 -109.1(3) . . . . ?
C6 C5 C8 C11 67.0(4) . . . . ?
C4 C5 C6 N1 -0.2(3) . . . . ?
C8 C5 C6 N1 -177.0(3) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C8 C5 C6 C7 3.4(5) . . . . ?
C21 C22 C23 N8 -0.9(3) . . . . ?
C19 C22 C23 N8 177.2(3) . . . . ?
C21 C22 C23 C24 179.0(3) . . . . ?
C19 C22 C23 C24 -2.9(5) . . . . ?
C23 C22 C21 N7 0.5(3) . . . . ?
C19 C22 C21 N7 -177.6(3) . . . . ?
C23 C22 C21 C20 -179.5(3) . . . . ?
C19 C22 C21 C20 2.4(5) . . . . ?
C10 C11 C12 N4 -0.2(3) . . . . ?
C8 C11 C12 N4 -178.6(3) . . . . ?
C10 C11 C12 C13 -178.2(3) . . . . ?
C8 C11 C12 C13 3.4(5) . . . . ?
C6 C5 C4 N2 0.3(3) . . . . ?
C8 C5 C4 N2 177.0(3) . . . . ?
C6 C5 C4 C3 177.5(3) . . . . ?
C8 C5 C4 C3 -5.8(5) . . . . ?
C12 C11 C10 N3 -0.2(3) . . . . ?
C8 C11 C10 N3 178.2(3) . . . . ?
C12 C11 C10 C9 178.3(3) . . . . ?
C8 C11 C10 C9 -3.3(5) . . . . ?
O5 C2 C1 P1 88.7(4) . . . . ?
O4 C2 C1 P1 -91.0(3) . . . . ?
O2 P1 C1 C2 171.2(2) . . . . ?
O3 P1 C1 C2 -63.9(3) . . . . ?
O1 P1 C1 C2 51.2(3) . . . . ?
C5 C6 N1 N2 0.0(3) . . . . ?
C7 C6 N1 N2 179.6(3) . . . . ?
C22 C21 N7 N8 0.1(3) . . . . ?
C20 C21 N7 N8 -179.9(3) . . . . ?
C11 C12 N4 N3 0.5(3) . . . . ?
C13 C12 N4 N3 178.7(3) . . . . ?
C6 N1 N2 C4 0.2(3) . . . . ?
C5 C4 N2 N1 -0.3(3) . . . . ?
C3 C4 N2 N1 -177.9(3) . . . . ?
C11 C10 N3 N4 0.5(3) . . . . ?
C9 C10 N3 N4 -178.2(3) . . . . ?
C12 N4 N3 C10 -0.6(3) . . . . ?
C16 C15 N5 N6 -1.1(3) . . . . ?
C14 C15 N5 N6 -179.6(3) . . . . ?
C22 C23 N8 N7 1.0(3) . . . . ?
C24 C23 N8 N7 -178.9(3) . . . . ?
C21 N7 N8 C23 -0.7(3) . . . . ?
C16 C17 N6 N5 0.8(3) . . . . ?
C18 C17 N6 N5 -177.0(3) . . . . ?
C15 N5 N6 C17 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 980598'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1186shi_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C11 H17 N4, C11 H16 N4, C6 H7 O3 P, C6 H6 O3 P'
_chemical_formula_sum            'C34 H46 N8 O6 P2'
_chemical_formula_weight         724.73

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 c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'

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

_cell_length_a                   26.1677(10)
_cell_length_b                   16.0917(8)
_cell_length_c                   8.6296(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3633.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    126
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536.0
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62864
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         28.29
_reflns_number_total             8834
_reflns_number_gt                5339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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)+(0.0765P)²+0.2956P] where P=(Fo²+2Fc²)/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   0.33(10)
_refine_ls_number_reflns         8834
_refine_ls_number_parameters     463
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_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
P1 P 0.53943(3) 0.15299(5) 1.22867(11) 0.0415(2) Uani 1 1 d . . .
P2 P 0.94282(3) 0.65756(5) 0.35766(11) 0.0426(2) Uani 1 1 d . . .
O6 O 0.99491(9) 0.63684(14) 0.2791(3) 0.0521(6) Uani 1 1 d . . .
H6E H 1.0129 0.6786 0.2777 0.078 Uiso 1 1 calc R . .
O5 O 0.90692(9) 0.58962(15) 0.3048(3) 0.0573(7) Uani 1 1 d . . .
O4 O 0.92552(8) 0.74390(14) 0.3207(3) 0.0589(7) Uani 1 1 d . . .
O3 O 0.55550(8) 0.23805(14) 1.2793(3) 0.0531(6) Uani 1 1 d . . .
O2 O 0.48406(8) 0.13221(14) 1.2770(3) 0.0540(6) Uani 1 1 d . . .
H2E H 0.4676 0.1753 1.2849 0.081 Uiso 1 1 calc R . .
O1 O 0.57217(9) 0.08360(16) 1.2974(3) 0.0578(7) Uani 1 1 d . . .
H1E H 0.5990 0.0800 1.2488 0.087 Uiso 1 1 calc R . .
N1 N 0.69356(9) 0.23967(14) 0.3871(3) 0.0405(7) Uani 1 1 d . . .
N2 N 0.64821(10) 0.27714(14) 0.4184(3) 0.0411(6) Uani 1 1 d . . .
H2D H 0.6193 0.2598 0.3837 0.049 Uiso 1 1 calc R . .
N3 N 0.77918(10) 0.58919(14) 0.3989(3) 0.0411(7) Uani 1 1 d . . .
H3D H 0.7761 0.6325 0.3411 0.049 Uiso 1 1 calc R . .
N4 N 0.82377(10) 0.55295(15) 0.4354(3) 0.0402(6) Uani 1 1 d . . .
H4D H 0.8536 0.5691 0.4064 0.048 Uiso 1 1 calc R . .
N5 N 0.78628(9) 0.73765(14) 0.2131(3) 0.0395(6) Uani 1 1 d . . .
N6 N 0.83149(10) 0.77441(15) 0.1795(3) 0.0407(7) Uani 1 1 d . . .
H6D H 0.8605 0.7571 0.2134 0.049 Uiso 1 1 calc R . .
N7 N 0.65710(10) 1.05049(14) 0.1754(3) 0.0403(6) Uani 1 1 d . . .
N8 N 0.70230(9) 1.08470(14) 0.2125(3) 0.0372(6) Uani 1 1 d . . .
H8D H 0.7059 1.1267 0.2732 0.045 Uiso 1 1 calc R . .
C1 C 0.54369(13) 0.14557(19) 1.0225(4) 0.0411(8) Uani 1 1 d . . .
C2 C 0.51479(14) 0.0899(2) 0.9386(5) 0.0530(9) Uani 1 1 d . . .
H2 H 0.4913 0.0562 0.9893 0.064 Uiso 1 1 calc R . .
C3 C 0.52040(19) 0.0838(3) 0.7796(5) 0.0771(13) Uani 1 1 d . . .
H3 H 0.4999 0.0474 0.7234 0.092 Uiso 1 1 calc R . .
C4 C 0.5567(2) 0.1319(4) 0.7041(6) 0.0923(16) Uani 1 1 d . . .
H4 H 0.5612 0.1268 0.5977 0.111 Uiso 1 1 calc R . .
C5 C 0.5856(2) 0.1869(3) 0.7862(6) 0.0842(14) Uani 1 1 d . . .
H5 H 0.6095 0.2199 0.7353 0.101 Uiso 1 1 calc R . .
C6 C 0.57966(15) 0.1937(3) 0.9450(5) 0.0630(10) Uani 1 1 d . . .
H6A H 0.5999 0.2307 1.0004 0.076 Uiso 1 1 calc R . .
C7 C 0.95219(12) 0.64830(18) 0.5623(4) 0.0365(8) Uani 1 1 d . . .
C8 C 0.96684(14) 0.5741(2) 0.6269(4) 0.0517(9) Uani 1 1 d . . .
H8 H 0.9726 0.5288 0.5624 0.062 Uiso 1 1 calc R . .
C9 C 0.97318(18) 0.5650(3) 0.7826(5) 0.0732(12) Uani 1 1 d . . .
H9 H 0.9827 0.5135 0.8221 0.088 Uiso 1 1 calc R . .
C10 C 0.96590(19) 0.6289(3) 0.8803(6) 0.0880(14) Uani 1 1 d . . .
H10 H 0.9709 0.6225 0.9863 0.106 Uiso 1 1 calc R . .
C11 C 0.9512(2) 0.7023(3) 0.8214(6) 0.105(2) Uani 1 1 d . . .
H11 H 0.9454 0.7466 0.8884 0.126 Uiso 1 1 calc R . .
C12 C 0.94443(17) 0.7141(2) 0.6620(6) 0.0745(13) Uani 1 1 d . . .
H12 H 0.9348 0.7658 0.6237 0.089 Uiso 1 1 calc R . .
C13 C 0.78299(12) 0.2626(2) 0.4532(5) 0.0485(9) Uani 1 1 d . . .
H13A H 0.7863 0.2080 0.4095 0.073 Uiso 1 1 calc R . .
H13B H 0.7973 0.2631 0.5557 0.073 Uiso 1 1 calc R . .
H13C H 0.8009 0.3019 0.3894 0.073 Uiso 1 1 calc R . .
C14 C 0.72838(11) 0.28549(16) 0.4609(4) 0.0343(7) Uani 1 1 d . . .
C15 C 0.70501(11) 0.35224(17) 0.5389(3) 0.0329(7) Uani 1 1 d . . .
C16 C 0.65360(12) 0.34430(17) 0.5094(4) 0.0378(7) Uani 1 1 d . . .
C17 C 0.60766(13) 0.3934(2) 0.5615(5) 0.0579(10) Uani 1 1 d . . .
H17A H 0.6079 0.4469 0.5124 0.087 Uiso 1 1 calc R . .
H17B H 0.6088 0.4003 0.6720 0.087 Uiso 1 1 calc R . .
H17C H 0.5770 0.3642 0.5334 0.087 Uiso 1 1 calc R . .
C18 C 0.73097(12) 0.41776(17) 0.6357(4) 0.0379(7) Uani 1 1 d . . .
H18A H 0.7052 0.4458 0.6975 0.046 Uiso 1 1 calc R . .
H18B H 0.7543 0.3905 0.7066 0.046 Uiso 1 1 calc R . .
C19 C 0.68598(13) 0.5773(2) 0.4464(5) 0.0540(9) Uani 1 1 d . . .
H19A H 0.6847 0.6368 0.4528 0.081 Uiso 1 1 calc R . .
H19B H 0.6654 0.5537 0.5273 0.081 Uiso 1 1 calc R . .
H19C H 0.6732 0.5597 0.3475 0.081 Uiso 1 1 calc R . .
C20 C 0.74032(12) 0.54870(16) 0.4647(4) 0.0361(7) Uani 1 1 d . . .
C21 C 0.76018(11) 0.48202(16) 0.5458(3) 0.0335(7) Uani 1 1 d . . .
C22 C 0.81345(13) 0.48702(18) 0.5251(4) 0.0403(8) Uani 1 1 d . . .
C23 C 0.85625(13) 0.4367(2) 0.5893(5) 0.0557(10) Uani 1 1 d . . .
H23A H 0.8696 0.4010 0.5099 0.084 Uiso 1 1 calc R . .
H23B H 0.8440 0.4037 0.6741 0.084 Uiso 1 1 calc R . .
H23C H 0.8828 0.4731 0.6252 0.084 Uiso 1 1 calc R . .
C24 C 0.69599(12) 0.7612(2) 0.1492(5) 0.0509(9) Uani 1 1 d . . .
H24A H 0.6927 0.7031 0.1722 0.076 Uiso 1 1 calc R . .
H24B H 0.6796 0.7731 0.0522 0.076 Uiso 1 1 calc R . .
H24C H 0.6801 0.7932 0.2300 0.076 Uiso 1 1 calc R . .
C25 C 0.75105(13) 0.78341(16) 0.1390(4) 0.0345(7) Uani 1 1 d . . .
C26 C 0.77416(11) 0.85006(16) 0.0590(3) 0.0317(7) Uani 1 1 d . . .
C27 C 0.82590(12) 0.84129(17) 0.0868(4) 0.0361(7) Uani 1 1 d . . .
C28 C 0.87096(12) 0.8893(2) 0.0323(4) 0.0524(9) Uani 1 1 d . . .
H28A H 0.8894 0.9104 0.1201 0.079 Uiso 1 1 calc R . .
H28B H 0.8597 0.9348 -0.0310 0.079 Uiso 1 1 calc R . .
H28C H 0.8929 0.8537 -0.0272 0.079 Uiso 1 1 calc R . .
C29 C 0.74776(13) 0.91585(15) -0.0361(4) 0.0365(7) Uani 1 1 d . . .
H29A H 0.7731 0.9435 -0.0998 0.044 Uiso 1 1 calc R . .
H29B H 0.7237 0.8888 -0.1053 0.044 Uiso 1 1 calc R . .
C30 C 0.62426(13) 0.9386(2) 0.0108(5) 0.0584(10) Uani 1 1 d . . .
H30A H 0.6003 0.9239 0.0905 0.088 Uiso 1 1 calc R . .
H30B H 0.6376 0.8890 -0.0359 0.088 Uiso 1 1 calc R . .
H30C H 0.6074 0.9715 -0.0666 0.088 Uiso 1 1 calc R . .
C31 C 0.66711(12) 0.98748(18) 0.0800(4) 0.0378(7) Uani 1 1 d . . .
C32 C 0.71959(11) 0.98043(16) 0.0557(3) 0.0304(7) Uani 1 1 d . . .
C33 C 0.74120(12) 1.04490(16) 0.1428(3) 0.0340(7) Uani 1 1 d . . .
C34 C 0.79482(12) 1.0714(2) 0.1606(4) 0.0464(9) Uani 1 1 d . . .
H34A H 0.7958 1.1280 0.1953 0.070 Uiso 1 1 calc R . .
H34B H 0.8120 1.0669 0.0627 0.070 Uiso 1 1 calc R . .
H34C H 0.8115 1.0364 0.2353 0.070 Uiso 1 1 calc R . .


_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
P1 O3 1.497(2) . ?
P1 O1 1.527(2) . ?
P1 O2 1.545(2) . ?
P1 C1 1.786(4) . ?
P2 O4 1.496(2) . ?
P2 O5 1.512(2) . ?
P2 O6 1.558(2) . ?
P2 C7 1.789(4) . ?
O6 H6E 0.8200 . ?
O2 H2E 0.8200 . ?
O1 H1E 0.8200 . ?
N1 C14 1.334(4) . ?
N1 N2 1.358(3) . ?
N2 C16 1.344(4) . ?
N2 H2D 0.8600 . ?
N3 C20 1.335(4) . ?
N3 N4 1.342(4) . ?
N3 H3D 0.8600 . ?
N4 C22 1.341(4) . ?
N4 H4D 0.8600 . ?
N5 C25 1.342(4) . ?
N5 N6 1.354(3) . ?
N6 C27 1.349(4) . ?
N6 H6D 0.8600 . ?
N7 C31 1.333(4) . ?
N7 N8 1.343(3) . ?
N8 C33 1.345(4) . ?
N8 H8D 0.8600 . ?
C1 C2 1.378(5) . ?
C1 C6 1.390(5) . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.372(4) . ?
C7 C12 1.379(5) . ?
C8 C9 1.362(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.344(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.342(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.400(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.477(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.407(4) . ?
C15 C16 1.375(4) . ?
C15 C18 1.507(4) . ?
C16 C17 1.507(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C21 1.502(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.503(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.382(4) . ?
C21 C22 1.407(4) . ?
C22 C23 1.489(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.487(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.412(4) . ?
C26 C27 1.382(4) . ?
C26 C29 1.507(4) . ?
C27 C28 1.486(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C32 1.500(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.494(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C32 1.394(4) . ?
C32 C33 1.400(4) . ?
C33 C34 1.474(4) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
O3 P1 O1 113.43(15) . . ?
O3 P1 O2 112.49(13) . . ?
O1 P1 O2 105.24(14) . . ?
O3 P1 C1 109.52(15) . . ?
O1 P1 C1 107.65(14) . . ?
O2 P1 C1 108.25(15) . . ?
O4 P2 O5 114.78(14) . . ?
O4 P2 O6 111.75(13) . . ?
O5 P2 O6 104.93(14) . . ?
O4 P2 C7 109.24(15) . . ?
O5 P2 C7 108.81(14) . . ?
O6 P2 C7 106.97(15) . . ?
P2 O6 H6E 109.5 . . ?
P1 O2 H2E 109.5 . . ?
P1 O1 H1E 109.5 . . ?
C14 N1 N2 104.9(2) . . ?
C16 N2 N1 112.4(2) . . ?
C16 N2 H2D 123.8 . . ?
N1 N2 H2D 123.8 . . ?
C20 N3 N4 110.5(2) . . ?
C20 N3 H3D 124.7 . . ?
N4 N3 H3D 124.7 . . ?
C22 N4 N3 107.7(3) . . ?
C22 N4 H4D 126.1 . . ?
N3 N4 H4D 126.1 . . ?
C25 N5 N6 105.0(2) . . ?
C27 N6 N5 112.4(2) . . ?
C27 N6 H6D 123.8 . . ?
N5 N6 H6D 123.8 . . ?
C31 N7 N8 106.6(2) . . ?
N7 N8 C33 111.4(2) . . ?
N7 N8 H8D 124.3 . . ?
C33 N8 H8D 124.3 . . ?
C2 C1 C6 118.7(4) . . ?
C2 C1 P1 122.2(3) . . ?
C6 C1 P1 119.0(3) . . ?
C1 C2 C3 120.7(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C8 C7 C12 117.1(4) . . ?
C8 C7 P2 120.8(3) . . ?
C12 C7 P2 122.1(3) . . ?
C9 C8 C7 121.9(4) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 118.5(5) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 121.9(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C11 119.3(4) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 110.7(3) . . ?
N1 C14 C13 120.1(3) . . ?
C15 C14 C13 129.2(3) . . ?
C16 C15 C14 105.4(3) . . ?
C16 C15 C18 127.5(3) . . ?
C14 C15 C18 127.1(3) . . ?
N2 C16 C15 106.6(3) . . ?
N2 C16 C17 120.8(3) . . ?
C15 C16 C17 132.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 C15 115.1(2) . . ?
C21 C18 H18A 108.5 . . ?
C15 C18 H18A 108.5 . . ?
C21 C18 H18B 108.5 . . ?
C15 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C20 C21 107.9(3) . . ?
N3 C20 C19 121.8(3) . . ?
C21 C20 C19 130.3(3) . . ?
C20 C21 C22 105.3(3) . . ?
C20 C21 C18 127.2(3) . . ?
C22 C21 C18 127.5(3) . . ?
N4 C22 C21 108.5(3) . . ?
N4 C22 C23 119.6(3) . . ?
C21 C22 C23 131.8(3) . . ?
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 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 C26 110.8(3) . . ?
N5 C25 C24 120.4(3) . . ?
C26 C25 C24 128.8(3) . . ?
C27 C26 C25 104.9(2) . . ?
C27 C26 C29 128.0(3) . . ?
C25 C26 C29 127.1(3) . . ?
N6 C27 C26 106.9(3) . . ?
N6 C27 C28 121.1(3) . . ?
C26 C27 C28 132.0(3) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C32 C29 C26 115.1(3) . . ?
C32 C29 H29A 108.5 . . ?
C26 C29 H29A 108.5 . . ?
C32 C29 H29B 108.5 . . ?
C26 C29 H29B 108.5 . . ?
H29A C29 H29B 107.5 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N7 C31 C32 110.4(3) . . ?
N7 C31 C30 120.0(3) . . ?
C32 C31 C30 129.5(3) . . ?
C31 C32 C33 104.9(2) . . ?
C31 C32 C29 128.3(3) . . ?
C33 C32 C29 126.7(3) . . ?
N8 C33 C32 106.7(3) . . ?
N8 C33 C34 122.4(3) . . ?
C32 C33 C34 130.9(3) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
C14 N1 N2 C16 -0.3(3) . . . . ?
C20 N3 N4 C22 0.8(3) . . . . ?
C25 N5 N6 C27 -0.1(3) . . . . ?
C31 N7 N8 C33 0.0(3) . . . . ?
O3 P1 C1 C2 -155.1(3) . . . . ?
O1 P1 C1 C2 81.1(3) . . . . ?
O2 P1 C1 C2 -32.2(3) . . . . ?
O3 P1 C1 C6 29.1(3) . . . . ?
O1 P1 C1 C6 -94.6(3) . . . . ?
O2 P1 C1 C6 152.1(3) . . . . ?
C6 C1 C2 C3 -1.9(5) . . . . ?
P1 C1 C2 C3 -177.6(3) . . . . ?
C1 C2 C3 C4 2.2(7) . . . . ?
C2 C3 C4 C5 -1.8(7) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C1 -0.9(8) . . . . ?
C2 C1 C6 C5 1.2(6) . . . . ?
P1 C1 C6 C5 177.1(4) . . . . ?
O4 P2 C7 C8 178.3(3) . . . . ?
O5 P2 C7 C8 52.3(3) . . . . ?
O6 P2 C7 C8 -60.6(3) . . . . ?
O4 P2 C7 C12 -0.8(4) . . . . ?
O5 P2 C7 C12 -126.8(3) . . . . ?
O6 P2 C7 C12 120.3(3) . . . . ?
C12 C7 C8 C9 0.5(6) . . . . ?
P2 C7 C8 C9 -178.6(3) . . . . ?
C7 C8 C9 C10 -0.8(7) . . . . ?
C8 C9 C10 C11 1.2(8) . . . . ?
C9 C10 C11 C12 -1.3(9) . . . . ?
C8 C7 C12 C11 -0.6(6) . . . . ?
P2 C7 C12 C11 178.5(4) . . . . ?
C10 C11 C12 C7 1.1(8) . . . . ?
N2 N1 C14 C15 -0.1(3) . . . . ?
N2 N1 C14 C13 179.8(3) . . . . ?
N1 C14 C15 C16 0.4(3) . . . . ?
C13 C14 C15 C16 -179.4(3) . . . . ?
N1 C14 C15 C18 179.7(3) . . . . ?
C13 C14 C15 C18 -0.1(5) . . . . ?
N1 N2 C16 C15 0.6(3) . . . . ?
N1 N2 C16 C17 -178.2(3) . . . . ?
C14 C15 C16 N2 -0.6(3) . . . . ?
C18 C15 C16 N2 -179.9(3) . . . . ?
C14 C15 C16 C17 178.0(4) . . . . ?
C18 C15 C16 C17 -1.3(6) . . . . ?
C16 C15 C18 C21 -106.8(4) . . . . ?
C14 C15 C18 C21 74.0(4) . . . . ?
N4 N3 C20 C21 -1.1(3) . . . . ?
N4 N3 C20 C19 178.4(3) . . . . ?
N3 C20 C21 C22 1.0(3) . . . . ?
C19 C20 C21 C22 -178.5(3) . . . . ?
N3 C20 C21 C18 -178.6(3) . . . . ?
C19 C20 C21 C18 1.9(5) . . . . ?
C15 C18 C21 C20 76.9(4) . . . . ?
C15 C18 C21 C22 -102.7(4) . . . . ?
N3 N4 C22 C21 -0.2(3) . . . . ?
N3 N4 C22 C23 -177.3(3) . . . . ?
C20 C21 C22 N4 -0.5(3) . . . . ?
C18 C21 C22 N4 179.1(3) . . . . ?
C20 C21 C22 C23 176.2(3) . . . . ?
C18 C21 C22 C23 -4.2(5) . . . . ?
N6 N5 C25 C26 -0.5(3) . . . . ?
N6 N5 C25 C24 179.9(3) . . . . ?
N5 C25 C26 C27 1.0(3) . . . . ?
C24 C25 C26 C27 -179.5(3) . . . . ?
N5 C25 C26 C29 -179.2(3) . . . . ?
C24 C25 C26 C29 0.3(5) . . . . ?
N5 N6 C27 C26 0.8(3) . . . . ?
N5 N6 C27 C28 -178.3(3) . . . . ?
C25 C26 C27 N6 -1.0(3) . . . . ?
C29 C26 C27 N6 179.2(3) . . . . ?
C25 C26 C27 C28 177.9(3) . . . . ?
C29 C26 C27 C28 -1.9(5) . . . . ?
C27 C26 C29 C32 -106.2(4) . . . . ?
C25 C26 C29 C32 74.0(4) . . . . ?
N8 N7 C31 C32 0.4(3) . . . . ?
N8 N7 C31 C30 -177.0(3) . . . . ?
N7 C31 C32 C33 -0.6(3) . . . . ?
C30 C31 C32 C33 176.5(3) . . . . ?
N7 C31 C32 C29 176.4(3) . . . . ?
C30 C31 C32 C29 -6.4(5) . . . . ?
C26 C29 C32 C31 -103.3(4) . . . . ?
C26 C29 C32 C33 73.1(4) . . . . ?
N7 N8 C33 C32 -0.4(3) . . . . ?
N7 N8 C33 C34 178.3(3) . . . . ?
C31 C32 C33 N8 0.6(3) . . . . ?
C29 C32 C33 N8 -176.5(3) . . . . ?
C31 C32 C33 C34 -177.9(3) . . . . ?
C29 C32 C33 C34 4.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 980599'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1234shi_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H17 N4, C3 H6 O5 P'
_chemical_formula_sum            'C14 H23 N4 O5 P'
_chemical_formula_weight         358.33

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   10.364(3)
_cell_length_b                   16.227(4)
_cell_length_c                   11.093(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.843(12)
_cell_angle_gamma                90.00
_cell_volume                     1818.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    126
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.0
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22721
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_sigmaI/netI    0.3180
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3197
_reflns_number_gt                2217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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)+(0.0947P)²+0.2920P] where P=(Fo²+2Fc²)/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_number_reflns         3197
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
P1 P 0.39650(7) 0.06475(3) 0.60588(5) 0.0281(2) Uani 1 1 d . . .
O1 O 0.5515(2) 0.06168(10) 0.64454(15) 0.0391(5) Uani 1 1 d . . .
H1E H 0.5812 0.0475 0.5851 0.059 Uiso 1 1 calc R . .
O2 O 0.3403(2) -0.01068(9) 0.53367(15) 0.0390(5) Uani 1 1 d . . .
O3 O 0.3478(2) 0.08037(9) 0.72229(14) 0.0395(5) Uani 1 1 d . . .
O4 O 0.3147(3) 0.36128(12) 0.49792(19) 0.0654(8) Uani 1 1 d . . .
O5 O 0.4319(2) 0.30166(10) 0.37849(15) 0.0449(5) Uani 1 1 d . . .
H5Z H 0.4157 0.3447 0.3392 0.067 Uiso 1 1 calc R . .
N1 N 0.1673(3) 0.50445(11) 0.30311(18) 0.0350(6) Uani 1 1 d . . .
H1D H 0.2284 0.4799 0.2756 0.042 Uiso 1 1 calc R . .
N2 N 0.0380(3) 0.49307(10) 0.26134(17) 0.0327(6) Uani 1 1 d . . .
H2D H 0.0026 0.4600 0.2026 0.039 Uiso 1 1 calc R . .
N3 N 0.1558(3) 0.86072(11) 0.49550(17) 0.0375(6) Uani 1 1 d . . .
H3D H 0.2041 0.9025 0.5240 0.045 Uiso 1 1 calc R . .
N4 N 0.0626(3) 0.86131(11) 0.38812(18) 0.0388(6) Uani 1 1 d . . .
C4 C 0.3234(3) 0.58438(17) 0.4599(3) 0.0478(7) Uani 1 1 d . . .
H4B H 0.3393 0.5664 0.5444 0.072 Uiso 1 1 calc R . .
H4C H 0.3320 0.6432 0.4574 0.072 Uiso 1 1 calc R . .
H4A H 0.3867 0.5592 0.4201 0.072 Uiso 1 1 calc R . .
C5 C 0.1878(3) 0.56017(12) 0.3948(2) 0.0308(6) Uani 1 1 d . . .
C6 C 0.0645(3) 0.58563(11) 0.41078(18) 0.0255(6) Uani 1 1 d . . .
C7 C -0.0293(3) 0.54130(12) 0.32529(18) 0.0279(6) Uani 1 1 d . . .
C8 C -0.1747(3) 0.53942(14) 0.2987(2) 0.0390(7) Uani 1 1 d . . .
H8B H -0.2094 0.5705 0.2250 0.058 Uiso 1 1 calc R . .
H8C H -0.2049 0.5632 0.3668 0.058 Uiso 1 1 calc R . .
H8A H -0.2047 0.4834 0.2871 0.058 Uiso 1 1 calc R . .
C9 C 0.0368(3) 0.64734(11) 0.50428(18) 0.0287(6) Uani 1 1 d . . .
H9A H 0.0868 0.6316 0.5856 0.034 Uiso 1 1 calc R . .
H9B H -0.0564 0.6445 0.5056 0.034 Uiso 1 1 calc R . .
C14 C -0.0971(3) 0.76250(15) 0.2705(2) 0.0451(8) Uani 1 1 d . . .
H14C H -0.1293 0.8113 0.2246 0.068 Uiso 1 1 calc R . .
H14B H -0.1681 0.7366 0.2989 0.068 Uiso 1 1 calc R . .
H14A H -0.0629 0.7251 0.2182 0.068 Uiso 1 1 calc R . .
C13 C 0.0098(3) 0.78503(12) 0.37829(19) 0.0308(6) Uani 1 1 d . . .
C12 C 0.0709(3) 0.73621(11) 0.47960(18) 0.0260(6) Uani 1 1 d . . .
C11 C 0.1635(3) 0.78626(12) 0.55268(19) 0.0310(6) Uani 1 1 d . . .
C10 C 0.2601(3) 0.77157(16) 0.6727(2) 0.0468(8) Uani 1 1 d . . .
H10C H 0.3338 0.8085 0.6795 0.070 Uiso 1 1 calc R . .
H10B H 0.2910 0.7157 0.6757 0.070 Uiso 1 1 calc R . .
H10A H 0.2175 0.7811 0.7400 0.070 Uiso 1 1 calc R . .
C3 C 0.3836(3) 0.30585(13) 0.4791(2) 0.0353(6) Uani 1 1 d . . .
C2 C 0.4240(3) 0.23387(13) 0.5636(2) 0.0424(8) Uani 1 1 d . . .
H2B H 0.3989 0.2442 0.6415 0.051 Uiso 1 1 calc R . .
H2A H 0.5194 0.2279 0.5806 0.051 Uiso 1 1 calc R . .
C1 C 0.3588(3) 0.15340(13) 0.5069(2) 0.0389(7) Uani 1 1 d . . .
H1A H 0.3871 0.1426 0.4307 0.047 Uiso 1 1 calc R . .
H1B H 0.2636 0.1611 0.4859 0.047 Uiso 1 1 calc R . .


_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
P1 O2 1.5072(16) . ?
P1 O3 1.5087(16) . ?
P1 O1 1.569(2) . ?
P1 C1 1.799(2) . ?
O1 H1E 0.8200 . ?
O4 C3 1.196(3) . ?
O5 C3 1.323(3) . ?
O5 H5Z 0.8200 . ?
N1 N2 1.330(3) . ?
N1 C5 1.342(3) . ?
N1 H1D 0.8600 . ?
N2 C7 1.350(3) . ?
N2 H2D 0.8600 . ?
N3 N4 1.356(3) . ?
N3 C11 1.359(3) . ?
N3 H3D 0.8600 . ?
N4 C13 1.348(3) . ?
C4 C5 1.483(4) . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4A 0.9600 . ?
C5 C6 1.391(4) . ?
C6 C7 1.397(3) . ?
C6 C9 1.515(3) . ?
C7 C8 1.470(4) . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8A 0.9600 . ?
C9 C12 1.524(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C14 C13 1.484(4) . ?
C14 H14C 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14A 0.9600 . ?
C13 C12 1.405(3) . ?
C12 C11 1.376(3) . ?
C11 C10 1.497(4) . ?
C10 H10C 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10A 0.9600 . ?
C3 C2 1.498(3) . ?
C2 C1 1.539(3) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
O2 P1 O3 115.35(10) . . ?
O2 P1 O1 111.76(10) . . ?
O3 P1 O1 106.76(10) . . ?
O2 P1 C1 108.61(11) . . ?
O3 P1 C1 108.63(11) . . ?
O1 P1 C1 105.22(12) . . ?
P1 O1 H1E 109.5 . . ?
C3 O5 H5Z 109.5 . . ?
N2 N1 C5 109.6(2) . . ?
N2 N1 H1D 125.2 . . ?
C5 N1 H1D 125.2 . . ?
N1 N2 C7 109.55(19) . . ?
N1 N2 H2D 125.2 . . ?
C7 N2 H2D 125.2 . . ?
N4 N3 C11 111.90(19) . . ?
N4 N3 H3D 124.0 . . ?
C11 N3 H3D 124.0 . . ?
C13 N4 N3 105.16(18) . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
N1 C5 C6 107.6(2) . . ?
N1 C5 C4 121.4(3) . . ?
C6 C5 C4 131.1(2) . . ?
C5 C6 C7 106.3(2) . . ?
C5 C6 C9 127.1(2) . . ?
C7 C6 C9 126.6(2) . . ?
N2 C7 C6 107.0(2) . . ?
N2 C7 C8 120.6(2) . . ?
C6 C7 C8 132.4(2) . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
C6 C9 C12 114.57(17) . . ?
C6 C9 H9A 108.6 . . ?
C12 C9 H9A 108.6 . . ?
C6 C9 H9B 108.6 . . ?
C12 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C13 C14 H14C 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 109.5 . . ?
N4 C13 C12 110.5(2) . . ?
N4 C13 C14 120.5(2) . . ?
C12 C13 C14 128.93(19) . . ?
C11 C12 C13 105.64(17) . . ?
C11 C12 C9 127.7(2) . . ?
C13 C12 C9 126.6(2) . . ?
N3 C11 C12 106.8(2) . . ?
N3 C11 C10 121.0(2) . . ?
C12 C11 C10 132.2(2) . . ?
C11 C10 H10C 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
C11 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 109.5 . . ?
O4 C3 O5 122.6(2) . . ?
O4 C3 C2 124.9(2) . . ?
O5 C3 C2 112.5(2) . . ?
C3 C2 C1 111.7(2) . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
H2B C2 H2A 107.9 . . ?
C2 C1 P1 114.37(18) . . ?
C2 C1 H1A 108.7 . . ?
P1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
P1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?

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
C5 N1 N2 C7 -0.1(2) . . . . ?
C11 N3 N4 C13 0.4(3) . . . . ?
N2 N1 C5 C6 -0.5(2) . . . . ?
N2 N1 C5 C4 179.3(2) . . . . ?
N1 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
N1 C5 C6 C9 179.35(18) . . . . ?
C4 C5 C6 C9 -0.4(4) . . . . ?
N1 N2 C7 C6 0.6(2) . . . . ?
N1 N2 C7 C8 -178.94(18) . . . . ?
C5 C6 C7 N2 -0.9(2) . . . . ?
C9 C6 C7 N2 -179.40(18) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
C9 C6 C7 C8 0.1(3) . . . . ?
C5 C6 C9 C12 69.9(3) . . . . ?
C7 C6 C9 C12 -111.8(3) . . . . ?
N3 N4 C13 C12 -0.4(3) . . . . ?
N3 N4 C13 C14 -180.0(2) . . . . ?
N4 C13 C12 C11 0.2(3) . . . . ?
C14 C13 C12 C11 179.8(3) . . . . ?
N4 C13 C12 C9 178.2(2) . . . . ?
C14 C13 C12 C9 -2.2(4) . . . . ?
C6 C9 C12 C11 -116.9(3) . . . . ?
C6 C9 C12 C13 65.5(3) . . . . ?
N4 N3 C11 C12 -0.3(3) . . . . ?
N4 N3 C11 C10 179.9(2) . . . . ?
C13 C12 C11 N3 0.0(3) . . . . ?
C9 C12 C11 N3 -177.9(2) . . . . ?
C13 C12 C11 C10 179.8(3) . . . . ?
C9 C12 C11 C10 1.9(5) . . . . ?
O4 C3 C2 C1 111.0(3) . . . . ?
O5 C3 C2 C1 -68.4(3) . . . . ?
C3 C2 C1 P1 -177.3(2) . . . . ?
O2 P1 C1 C2 -173.3(2) . . . . ?
O3 P1 C1 C2 60.5(3) . . . . ?
O1 P1 C1 C2 -53.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.128
_database_code_depnum_ccdc_archive 'CCDC 980600'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ups1302shi_1_0ma

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N4, 2(C4 H10 O3 P), C2 H6 O'
_chemical_formula_sum            'C21 H44 N4 O7 P2'
_chemical_formula_weight         526.51

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   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   11.6984(5)
_cell_length_b                   19.7930(8)
_cell_length_c                   25.4741(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.012(2)
_cell_angle_gamma                90.00
_cell_volume                     5894.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    117
_cell_measurement_theta_min      1.30
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2271.9
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65075
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             19847
_reflns_number_gt                13341
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker kappa Apex'
_computing_cell_refinement       'Bruker kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'Bruker XSHELL'

_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)+(0.0598P)²+0.0000P] where P=(Fo²+2Fc²)/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   0.03(5)
_refine_ls_number_reflns         19847
_refine_ls_number_parameters     1270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.001
_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
P1 P 0.94014(9) 0.84072(5) 0.12793(4) 0.0443(3) Uani 1 1 d . A 1
P2 P 0.87351(8) 0.60077(5) 0.08623(4) 0.0404(2) Uani 1 1 d . B 1
P3 P 0.57717(9) 0.34147(4) 0.12646(4) 0.0440(3) Uani 1 1 d . C 1
P4 P 0.63779(8) 0.10153(5) 0.08639(4) 0.0401(2) Uani 1 1 d . D 1
P5 P 0.11801(9) 0.40059(5) 0.36231(4) 0.0459(3) Uani 1 1 d . E 1
P6 P 0.17803(9) 0.16116(5) 0.41363(4) 0.0454(3) Uani 1 1 d . F 1
P7 P 0.55507(9) 0.40249(5) 0.63904(4) 0.0458(3) Uani 1 1 d . G 1
P8 P 0.62378(9) 0.16571(5) 0.58353(4) 0.0463(3) Uani 1 1 d . H 1
O1 O 0.8593(3) 0.78094(12) 0.11320(14) 0.0680(9) Uani 1 1 d . A 1
H1E H 0.8947 0.7453 0.1160 0.102 Uiso 1 1 calc R A 1
O2 O 1.0228(2) 0.82078(12) 0.17177(11) 0.0600(8) Uani 1 1 d . A 1
O3 O 0.8648(2) 0.89909(12) 0.14212(10) 0.0503(7) Uani 1 1 d . A 1
O4 O 0.9567(2) 0.53831(12) 0.08317(12) 0.0578(8) Uani 1 1 d . B 1
H4E H 0.9256 0.5048 0.0950 0.087 Uiso 1 1 calc R B 1
O5 O 0.7866(3) 0.58739(15) 0.12586(11) 0.0692(8) Uani 1 1 d . B 1
O6 O 0.9495(2) 0.66126(11) 0.09734(10) 0.0519(7) Uani 1 1 d . B 1
O7 O 0.6560(3) 0.28143(12) 0.11177(13) 0.0656(8) Uani 1 1 d . C 1
H7E H 0.6173 0.2471 0.1077 0.098 Uiso 1 1 calc R C 1
O8 O 0.4999(2) 0.32209(12) 0.17003(11) 0.0591(7) Uani 1 1 d . C 1
O9 O 0.6550(2) 0.39999(12) 0.14113(10) 0.0477(6) Uani 1 1 d . C 1
O10 O 0.5557(2) 0.03829(12) 0.08311(12) 0.0564(7) Uani 1 1 d . D 1
H10E H 0.5902 0.0048 0.0940 0.085 Uiso 1 1 calc R D 1
O11 O 0.7288(2) 0.08987(14) 0.12690(11) 0.0663(8) Uani 1 1 d . D 1
O12 O 0.5622(2) 0.16188(11) 0.09579(10) 0.0497(7) Uani 1 1 d . D 1
O13 O 0.1878(2) 0.46024(11) 0.34544(10) 0.0525(7) Uani 1 1 d . E 1
O14 O 0.0365(2) 0.37606(13) 0.31879(11) 0.0576(8) Uani 1 1 d . E 1
O15 O 0.2024(2) 0.34371(13) 0.38015(13) 0.0646(8) Uani 1 1 d . E 1
H15E H 0.1678 0.3078 0.3818 0.097 Uiso 1 1 calc R E 1
O16 O 0.0988(3) 0.10225(14) 0.39389(14) 0.0737(9) Uani 1 1 d . F 1
H16E H 0.1371 0.0680 0.3902 0.111 Uiso 1 1 calc R F 1
O17 O 0.1215(3) 0.22363(12) 0.39104(12) 0.0630(8) Uani 1 1 d . F 1
O18 O 0.3005(3) 0.14911(15) 0.40068(12) 0.0727(9) Uani 1 1 d . F 1
O19 O 0.6290(2) 0.46115(12) 0.65630(11) 0.0532(7) Uani 1 1 d . G 1
O20 O 0.4848(2) 0.37574(13) 0.68331(11) 0.0568(7) Uani 1 1 d . G 1
O21 O 0.6351(2) 0.34726(12) 0.61792(12) 0.0609(8) Uani 1 1 d . G 1
H21E H 0.6082 0.3099 0.6238 0.091 Uiso 1 1 calc R G 1
O22 O 0.5605(3) 0.22584(13) 0.60451(12) 0.0656(8) Uani 1 1 d . H 1
O23 O 0.7260(3) 0.14408(18) 0.61384(15) 0.1023(13) Uani 1 1 d . H 1
O24 O 0.5337(2) 0.10712(13) 0.58029(13) 0.0689(8) Uani 1 1 d . H 1
H24E H 0.5615 0.0729 0.5936 0.103 Uiso 1 1 calc R H 1
O25 O 0.4048(3) 0.48572(14) 0.38467(16) 0.0809(10) Uani 1 1 d . I 1
H25E H 0.3366 0.4797 0.3777 0.121 Uiso 1 1 calc R I 1
O26 O 0.8774(3) 0.42059(14) 0.1170(2) 0.0975(13) Uani 1 1 d . J 1
H26E H 0.8103 0.4146 0.1240 0.146 Uiso 1 1 calc R J 1
O27 O 0.1637(3) 0.97934(14) 0.38196(16) 0.0816(10) Uani 1 1 d . K 1
H27E H 0.2163 0.9678 0.3635 0.122 Uiso 1 1 calc R K 1
O28 O 0.6385(3) 0.92170(14) 0.1182(2) 0.0998(13) Uani 1 1 d . L 1
H28E H 0.7030 0.9165 0.1312 0.150 Uiso 1 1 calc R L 1
N1 N 1.1003(3) 0.62439(15) 0.32882(13) 0.0500(9) Uani 1 1 d . M 1
H1D H 1.1539 0.6317 0.3521 0.060 Uiso 1 1 calc R M 1
N2 N 1.0793(3) 0.56562(15) 0.30437(12) 0.0482(8) Uani 1 1 d . M 1
H2D H 1.1184 0.5292 0.3089 0.058 Uiso 1 1 calc R M 1
N3 N 0.6396(3) 0.77228(16) 0.31205(13) 0.0578(6) Uani 1 1 d . M 1
H3D H 0.6028 0.8086 0.3190 0.069 Uiso 1 1 calc R M 1
N4 N 0.6203(3) 0.71086(16) 0.33212(13) 0.0578(6) Uani 1 1 d . M 1
H4D H 0.5694 0.7017 0.3546 0.069 Uiso 1 1 calc R M 1
N5 N 0.6018(3) 0.56489(15) 0.17035(13) 0.0486(8) Uani 1 1 d . N 1
H5D H 0.6544 0.5724 0.1484 0.058 Uiso 1 1 calc R N 1
N6 N 0.5751(3) 0.50417(15) 0.19044(13) 0.0485(8) Uani 1 1 d . N 1
H6D H 0.6094 0.4669 0.1838 0.058 Uiso 1 1 calc R N 1
N7 N 0.1532(3) 0.72018(15) 0.18826(13) 0.0521(9) Uani 1 1 d . N 1
H7D H 0.1164 0.7572 0.1827 0.063 Uiso 1 1 calc R N 1
N8 N 0.1328(3) 0.66194(16) 0.16346(12) 0.0492(8) Uani 1 1 d . N 1
H8D H 0.0813 0.6556 0.1390 0.059 Uiso 1 1 calc R N 1
N9 N 0.9063(3) 0.27473(16) 0.31024(13) 0.0546(9) Uani 1 1 d . O 1
H9D H 0.9461 0.3102 0.3176 0.066 Uiso 1 1 calc R O 1
N10 N 0.9270(3) 0.21231(16) 0.32834(13) 0.0546(9) Uani 1 1 d . O 1
H10D H 0.9828 0.2014 0.3495 0.066 Uiso 1 1 calc R O 1
N11 N 0.4437(3) 0.13207(16) 0.33109(12) 0.0490(8) Uani 1 1 d . O 1
H11D H 0.3948 0.1390 0.3549 0.059 Uiso 1 1 calc R O 1
N12 N 0.4622(3) 0.07312(15) 0.30635(12) 0.0454(8) Uani 1 1 d . O 1
H12D H 0.4252 0.0363 0.3115 0.054 Uiso 1 1 calc R O 1
N13 N 0.3702(3) 0.22197(15) 0.18520(13) 0.0491(8) Uani 1 1 d . P 1
H13D H 0.4042 0.2594 0.1787 0.059 Uiso 1 1 calc R P 1
N14 N 0.3877(3) 0.16278(16) 0.16118(12) 0.0485(8) Uani 1 1 d . P 1
H14D H 0.4357 0.1561 0.1369 0.058 Uiso 1 1 calc R P 1
N15 N -0.0799(3) 0.06489(15) 0.17123(12) 0.0486(8) Uani 1 1 d . P 1
H15D H -0.1365 0.0723 0.1496 0.058 Uiso 1 1 calc R P 1
N16 N -0.0497(3) 0.00421(15) 0.19132(13) 0.0491(8) Uani 1 1 d . P 1
H16D H -0.0854 -0.0331 0.1852 0.059 Uiso 1 1 calc R P 1
C1 C 1.0947(6) 0.8033(2) 0.0547(2) 0.1016(19) Uani 1 1 d . A 1
H1B H 1.0467 0.7657 0.0450 0.152 Uiso 1 1 calc R A 1
H1C H 1.1457 0.7906 0.0833 0.152 Uiso 1 1 calc R A 1
H1A H 1.1384 0.8165 0.0251 0.152 Uiso 1 1 calc R A 1
C2 C 1.0201(5) 0.8628(2) 0.07148(19) 0.0763(15) Uani 1.00 1 d P A 1
C3 C 1.0993(7) 0.9235(3) 0.0869(3) 0.162(4) Uani 1 1 d . A 1
H3A H 1.1643 0.9237 0.0649 0.243 Uiso 1 1 calc R A 1
H3B H 1.1246 0.9191 0.1230 0.243 Uiso 1 1 calc R A 1
H3C H 1.0576 0.9649 0.0822 0.243 Uiso 1 1 calc R A 1
C4 C 0.9374(8) 0.8802(4) 0.0261(2) 0.168(4) Uani 1 1 d . A 1
H4A H 0.9790 0.8992 -0.0021 0.252 Uiso 1 1 calc R A 1
H4B H 0.8823 0.9124 0.0377 0.252 Uiso 1 1 calc R A 1
H4C H 0.8988 0.8400 0.0142 0.252 Uiso 1 1 calc R A 1
C5 C 0.8980(5) 0.6166(3) -0.01936(18) 0.106(2) Uani 1 1 d . B 1
H5A H 0.9472 0.5777 -0.0181 0.159 Uiso 1 1 calc R B 1
H5B H 0.9423 0.6565 -0.0119 0.159 Uiso 1 1 calc R B 1
H5C H 0.8622 0.6203 -0.0537 0.159 Uiso 1 1 calc R B 1
C6 C 0.7342(4) 0.5457(2) 0.01005(19) 0.0775(15) Uani 1 1 d . B 1
H6A H 0.7001 0.5488 -0.0247 0.116 Uiso 1 1 calc R B 1
H6B H 0.6752 0.5420 0.0352 0.116 Uiso 1 1 calc R B 1
H6C H 0.7825 0.5065 0.0124 0.116 Uiso 1 1 calc R B 1
C7 C 0.8056(4) 0.6089(2) 0.02170(16) 0.0548(11) Uani 1 1 d . B 1
C8 C 0.7254(5) 0.6700(2) 0.0224(2) 0.100(2) Uani 1 1 d . B 1
H8A H 0.7694 0.7104 0.0282 0.150 Uiso 1 1 calc R B 1
H8B H 0.6726 0.6647 0.0501 0.150 Uiso 1 1 calc R B 1
H8C H 0.6838 0.6732 -0.0107 0.150 Uiso 1 1 calc R B 1
C9 C 0.4126(5) 0.3041(2) 0.0522(2) 0.102(2) Uani 1 1 d . C 1
H9A H 0.3682 0.3163 0.0213 0.152 Uiso 1 1 calc R C 1
H9B H 0.3623 0.2932 0.0800 0.152 Uiso 1 1 calc R C 1
H9C H 0.4593 0.2656 0.0448 0.152 Uiso 1 1 calc R C 1
C10 C 0.4898(5) 0.3639(2) 0.0693(2) 0.0807(17) Uani 1 1 d . C 1
C11 C 0.4182(7) 0.4246(3) 0.0833(3) 0.162(4) Uani 1 1 d . C 1
H11A H 0.4675 0.4608 0.0948 0.244 Uiso 1 1 calc R C 1
H11B H 0.3683 0.4127 0.1109 0.244 Uiso 1 1 calc R C 1
H11C H 0.3734 0.4387 0.0529 0.244 Uiso 1 1 calc R C 1
C12 C 0.5713(8) 0.3795(4) 0.0239(2) 0.178(4) Uani 1 1 d . C 1
H12A H 0.5309 0.4049 -0.0029 0.266 Uiso 1 1 calc R C 1
H12B H 0.5979 0.3378 0.0093 0.266 Uiso 1 1 calc R C 1
H12C H 0.6355 0.4052 0.0372 0.266 Uiso 1 1 calc R C 1
C13 C 0.6035(5) 0.1149(3) -0.02035(19) 0.1003(19) Uani 1 1 d . D 1
H13A H 0.6367 0.1174 -0.0542 0.151 Uiso 1 1 calc R D 1
H13B H 0.5598 0.1551 -0.0144 0.151 Uiso 1 1 calc R D 1
H13C H 0.5542 0.0762 -0.0191 0.151 Uiso 1 1 calc R D 1
C14 C 0.7700(4) 0.0457(2) 0.01283(19) 0.0784(14) Uani 1 1 d . D 1
H14A H 0.7230 0.0062 0.0157 0.118 Uiso 1 1 calc R D 1
H14B H 0.8317 0.0438 0.0386 0.118 Uiso 1 1 calc R D 1
H14C H 0.8004 0.0476 -0.0216 0.118 Uiso 1 1 calc R D 1
C15 C 0.6981(3) 0.10854(19) 0.02203(16) 0.0533(10) Uani 0.99 1 d P D 1
C16 C 0.7773(5) 0.1706(2) 0.0222(2) 0.0977(19) Uani 1 1 d . D 1
H16A H 0.8041 0.1778 -0.0126 0.146 Uiso 1 1 calc R D 1
H16B H 0.8413 0.1631 0.0460 0.146 Uiso 1 1 calc R D 1
H16C H 0.7357 0.2097 0.0331 0.146 Uiso 1 1 calc R D 1
C17 C -0.0506(7) 0.4794(3) 0.4025(3) 0.145(3) Uani 1 1 d . E 1
H17A H -0.0967 0.4904 0.4318 0.218 Uiso 1 1 calc R E 1
H17B H -0.0990 0.4641 0.3737 0.218 Uiso 1 1 calc R E 1
H17C H -0.0092 0.5188 0.3921 0.218 Uiso 1 1 calc R E 1
C18 C 0.0349(5) 0.4228(2) 0.41867(18) 0.0716(14) Uani 1 1 d . E 1
C19 C -0.0325(5) 0.3611(2) 0.4368(2) 0.0920(17) Uani 1 1 d . E 1
H19A H -0.0721 0.3723 0.4680 0.138 Uiso 1 1 calc R E 1
H19B H 0.0193 0.3244 0.4441 0.138 Uiso 1 1 calc R E 1
H19C H -0.0869 0.3480 0.4096 0.138 Uiso 1 1 calc R E 1
C20 C 0.1157(8) 0.4468(4) 0.4627(2) 0.158(3) Uani 1 1 d . E 1
H20A H 0.1656 0.4809 0.4495 0.237 Uiso 1 1 calc R E 1
H20B H 0.1604 0.4094 0.4758 0.237 Uiso 1 1 calc R E 1
H20C H 0.0722 0.4654 0.4905 0.237 Uiso 1 1 calc R E 1
C25 C 0.3699(5) 0.4779(2) 0.6056(2) 0.0953(19) Uani 1 1 d . G 1
H25A H 0.4082 0.5171 0.6198 0.143 Uiso 1 1 calc R G 1
H25B H 0.3271 0.4566 0.6325 0.143 Uiso 1 1 calc R G 1
H25C H 0.3189 0.4912 0.5771 0.143 Uiso 1 1 calc R G 1
C26 C 0.4594(5) 0.4277(2) 0.58524(18) 0.0663(13) Uani 1 1 d . G 1
C27 C 0.3946(6) 0.3657(2) 0.5633(2) 0.105(2) Uani 1 1 d . G 1
H27A H 0.3392 0.3513 0.5879 0.157 Uiso 1 1 calc R G 1
H27B H 0.4478 0.3297 0.5577 0.157 Uiso 1 1 calc R G 1
H27C H 0.3564 0.3773 0.5305 0.157 Uiso 1 1 calc R G 1
C28 C 0.5255(7) 0.4622(3) 0.5443(2) 0.121(2) Uani 1 1 d . G 1
H28A H 0.4775 0.4686 0.5134 0.181 Uiso 1 1 calc R G 1
H28B H 0.5902 0.4349 0.5359 0.181 Uiso 1 1 calc R G 1
H28C H 0.5515 0.5052 0.5573 0.181 Uiso 1 1 calc R G 1
C29 C 0.7472(5) 0.2424(2) 0.5169(2) 0.0888(17) Uani 1 1 d . H 1
H29A H 0.8095 0.2343 0.5416 0.133 Uiso 1 1 calc R H 1
H29B H 0.7076 0.2828 0.5265 0.133 Uiso 1 1 calc R H 1
H29C H 0.7764 0.2477 0.4824 0.133 Uiso 1 1 calc R H 1
C30 C 0.6647(4) 0.1826(2) 0.51715(17) 0.0624(12) Uani 1 1 d . H 1
C31 C 0.7283(6) 0.1198(3) 0.4969(2) 0.123(2) Uani 1 1 d . H 1
H31A H 0.6807 0.0806 0.5002 0.184 Uiso 1 1 calc R H 1
H31B H 0.7980 0.1135 0.5173 0.184 Uiso 1 1 calc R H 1
H31C H 0.7456 0.1263 0.4607 0.184 Uiso 1 1 calc R H 1
C32 C 0.5577(6) 0.1976(4) 0.4824(2) 0.128(3) Uani 1 1 d . H 1
H32A H 0.5797 0.2052 0.4469 0.192 Uiso 1 1 calc R H 1
H32B H 0.5203 0.2372 0.4952 0.192 Uiso 1 1 calc R H 1
H32C H 0.5063 0.1598 0.4833 0.192 Uiso 1 1 calc R H 1
C33 C 0.9411(4) 0.5139(2) 0.24048(17) 0.0634(12) Uani 1 1 d . M 1
H33A H 0.9534 0.5213 0.2039 0.095 Uiso 1 1 calc R M 1
H33B H 0.8606 0.5097 0.2458 0.095 Uiso 1 1 calc R M 1
H33C H 0.9793 0.4732 0.2517 0.095 Uiso 1 1 calc R M 1
C34 C 0.9879(3) 0.57264(19) 0.27178(14) 0.0447(9) Uani 1 1 d . M 1
C35 C 0.9501(3) 0.63867(18) 0.27438(14) 0.0407(9) Uani 1 1 d . M 1
C36 C 1.0233(3) 0.67028(19) 0.31089(15) 0.0494(10) Uani 1 1 d . M 1
C37 C 1.0259(4) 0.7408(2) 0.3307(2) 0.0746(15) Uani 1 1 d . M 1
H37A H 0.9606 0.7487 0.3517 0.112 Uiso 1 1 calc R M 1
H37B H 1.0243 0.7716 0.3016 0.112 Uiso 1 1 calc R M 1
H37C H 1.0946 0.7479 0.3518 0.112 Uiso 1 1 calc R M 1
C38 C 0.8508(3) 0.6709(2) 0.24420(14) 0.0520(10) Uani 1 1 d . M 1
H38A H 0.8800 0.7066 0.2224 0.062 Uiso 1 1 calc R M 1
H38B H 0.8159 0.6372 0.2210 0.062 Uiso 1 1 calc R M 1
C39 C 0.6886(4) 0.59312(19) 0.32735(17) 0.0616(11) Uani 1 1 d . M 1
H39A H 0.6252 0.5855 0.3495 0.092 Uiso 1 1 calc R M 1
H39B H 0.7585 0.5814 0.3460 0.092 Uiso 1 1 calc R M 1
H39C H 0.6800 0.5657 0.2964 0.092 Uiso 1 1 calc R M 1
C40 C 0.6920(3) 0.66622(19) 0.31196(15) 0.0466(10) Uani 1 1 d . M 1
C41 C 0.7596(3) 0.69995(19) 0.27800(15) 0.0438(9) Uani 1 1 d . M 1
C42 C 0.7248(4) 0.7672(2) 0.27982(17) 0.0578(6) Uani 1 1 d . M 1
C43 C 0.7687(4) 0.8279(2) 0.2515(2) 0.0823(15) Uani 1 1 d . M 1
H43A H 0.7269 0.8673 0.2617 0.123 Uiso 1 1 calc R M 1
H43B H 0.7590 0.8212 0.2143 0.123 Uiso 1 1 calc R M 1
H43C H 0.8484 0.8341 0.2605 0.123 Uiso 1 1 calc R M 1
C44 C 0.4374(4) 0.4518(2) 0.24878(17) 0.0666(13) Uani 1 1 d . N 1
H44A H 0.3827 0.4301 0.2253 0.100 Uiso 1 1 calc R N 1
H44B H 0.4000 0.4665 0.2797 0.100 Uiso 1 1 calc R N 1
H44C H 0.4970 0.4204 0.2585 0.100 Uiso 1 1 calc R N 1
C45 C 0.4873(3) 0.51074(18) 0.22228(15) 0.0439(9) Uani 1 1 d . N 1
C46 C 0.4584(3) 0.57920(18) 0.22334(14) 0.0417(9) Uani 1 1 d . N 1
C47 C 0.5330(3) 0.61150(18) 0.19019(14) 0.0438(9) Uani 1 1 d . N 1
C48 C 0.5425(4) 0.68367(19) 0.17545(18) 0.0633(12) Uani 1 1 d . N 1
H48A H 0.6141 0.6912 0.1591 0.095 Uiso 1 1 calc R N 1
H48B H 0.5388 0.7112 0.2064 0.095 Uiso 1 1 calc R N 1
H48C H 0.4807 0.6954 0.1513 0.095 Uiso 1 1 calc R N 1
C49 C 0.3669(3) 0.61162(19) 0.25440(14) 0.0484(10) Uani 1 1 d . N 1
H49A H 0.4019 0.6451 0.2777 0.058 Uiso 1 1 calc R N 1
H49B H 0.3324 0.5775 0.2761 0.058 Uiso 1 1 calc R N 1
C50 C 0.2042(4) 0.5439(2) 0.16190(18) 0.0663(13) Uani 1 1 d . N 1
H50A H 0.1428 0.5389 0.1362 0.099 Uiso 1 1 calc R N 1
H50B H 0.1933 0.5129 0.1903 0.099 Uiso 1 1 calc R N 1
H50C H 0.2756 0.5344 0.1460 0.099 Uiso 1 1 calc R N 1
C51 C 0.2054(3) 0.61471(18) 0.18258(14) 0.0425(9) Uani 1 1 d . N 1
C52 C 0.2742(3) 0.64514(17) 0.22127(14) 0.0415(9) Uani 1 1 d . N 1
C53 C 0.2399(3) 0.71190(19) 0.22320(15) 0.0477(10) Uani 1 1 d . N 1
C54 C 0.2828(4) 0.7693(2) 0.25620(19) 0.0740(15) Uani 1 1 d . N 1
H54A H 0.3459 0.7904 0.2396 0.111 Uiso 1 1 calc R N 1
H54B H 0.3076 0.7527 0.2901 0.111 Uiso 1 1 calc R N 1
H54C H 0.2226 0.8016 0.2601 0.111 Uiso 1 1 calc R N 1
C55 C 0.7670(4) 0.3348(2) 0.25347(19) 0.0777(16) Uani 1 1 d . O 1
H55A H 0.7942 0.3736 0.2727 0.117 Uiso 1 1 calc R O 1
H55B H 0.6849 0.3337 0.2534 0.117 Uiso 1 1 calc R O 1
H55C H 0.7917 0.3373 0.2180 0.117 Uiso 1 1 calc R O 1
C56 C 0.8136(4) 0.2722(2) 0.27890(16) 0.0510(11) Uani 1 1 d . O 1
C57 C 0.7744(3) 0.20574(18) 0.27664(14) 0.0427(9) Uani 1 1 d . O 1
C58 C 0.8483(3) 0.1694(2) 0.30876(15) 0.0489(10) Uani 1 1 d . O 1
C59 C 0.8502(4) 0.0956(2) 0.32334(18) 0.0652(12) Uani 1 1 d . O 1
H59A H 0.7904 0.0865 0.3472 0.098 Uiso 1 1 calc R O 1
H59B H 0.9229 0.0846 0.3398 0.098 Uiso 1 1 calc R O 1
H59C H 0.8386 0.0687 0.2922 0.098 Uiso 1 1 calc R O 1
C60 C 0.6740(3) 0.1800(2) 0.24364(15) 0.0504(10) Uani 1 1 d . O 1
H60A H 0.7014 0.1475 0.2185 0.060 Uiso 1 1 calc R O 1
H60B H 0.6404 0.2175 0.2240 0.060 Uiso 1 1 calc R O 1
C61 C 0.5155(4) 0.2491(2) 0.33137(18) 0.0656(13) Uani 1 1 d . O 1
H61A H 0.4526 0.2554 0.3541 0.098 Uiso 1 1 calc R O 1
H61B H 0.5079 0.2795 0.3021 0.098 Uiso 1 1 calc R O 1
H61C H 0.5861 0.2580 0.3505 0.098 Uiso 1 1 calc R O 1
C62 C 0.5156(3) 0.17825(18) 0.31187(14) 0.0427(9) Uani 1 1 d . O 1
C63 C 0.5820(3) 0.14701(18) 0.27530(14) 0.0428(9) Uani 1 1 d . O 1
C64 C 0.5461(3) 0.08035(18) 0.27280(14) 0.0419(9) Uani 1 1 d . O 1
C65 C 0.5880(4) 0.02227(19) 0.24153(16) 0.0599(11) Uani 1 1 d . O 1
H65A H 0.5407 -0.0165 0.2472 0.090 Uiso 1 1 calc R O 1
H65B H 0.6656 0.0121 0.2524 0.090 Uiso 1 1 calc R O 1
H65C H 0.5849 0.0338 0.2049 0.090 Uiso 1 1 calc R O 1
C66 C 0.2508(4) 0.2702(2) 0.25373(19) 0.0700(13) Uani 1 1 d . P 1
H66A H 0.3027 0.3075 0.2513 0.105 Uiso 1 1 calc R P 1
H66B H 0.2478 0.2558 0.2896 0.105 Uiso 1 1 calc R P 1
H66C H 0.1759 0.2839 0.2414 0.105 Uiso 1 1 calc R P 1
C67 C 0.2916(3) 0.21266(18) 0.22059(15) 0.0458(10) Uani 1 1 d . P 1
C68 C 0.2565(3) 0.14553(18) 0.21935(14) 0.0410(9) Uani 1 1 d . P 1
C69 C 0.3194(3) 0.11578(18) 0.18073(15) 0.0421(9) Uani 1 1 d . P 1
C70 C 0.3186(4) 0.04441(19) 0.16080(18) 0.0644(12) Uani 1 1 d . P 1
H70A H 0.3782 0.0388 0.1362 0.097 Uiso 1 1 calc R P 1
H70B H 0.2460 0.0349 0.1437 0.097 Uiso 1 1 calc R P 1
H70C H 0.3311 0.0139 0.1897 0.097 Uiso 1 1 calc R P 1
C71 C 0.1709(3) 0.1119(2) 0.25367(14) 0.0483(10) Uani 1 1 d . P 1
H71A H 0.2098 0.0776 0.2748 0.058 Uiso 1 1 calc R P 1
H71B H 0.1410 0.1453 0.2774 0.058 Uiso 1 1 calc R P 1
C72 C -0.0216(4) 0.18370(19) 0.17595(17) 0.0598(12) Uani 1 1 d . P 1
H72A H -0.0962 0.1907 0.1599 0.090 Uiso 1 1 calc R P 1
H72B H 0.0357 0.1961 0.1517 0.090 Uiso 1 1 calc R P 1
H72C H -0.0133 0.2111 0.2069 0.090 Uiso 1 1 calc R P 1
C73 C -0.0078(3) 0.11160(18) 0.19036(14) 0.0438(9) Uani 1 1 d . P 1
C74 C 0.0730(3) 0.07987(18) 0.22357(14) 0.0402(9) Uani 1 1 d . P 1
C75 C 0.0444(3) 0.01117(18) 0.22228(15) 0.0453(9) Uani 1 1 d . P 1
C76 C 0.0995(4) -0.0483(2) 0.24812(18) 0.0697(14) Uani 1 1 d . P 1
H76A H 0.0490 -0.0865 0.2452 0.105 Uiso 1 1 calc R P 1
H76B H 0.1153 -0.0384 0.2845 0.105 Uiso 1 1 calc R P 1
H76C H 0.1696 -0.0585 0.2313 0.105 Uiso 1 1 calc R P 1
C77 C -0.0107(6) 0.9213(4) 0.3950(3) 0.134(3) Uani 1 1 d . K 1
H77A H -0.0415 0.9635 0.4066 0.201 Uiso 1 1 calc R K 1
H77B H -0.0426 0.8850 0.4147 0.201 Uiso 1 1 calc R K 1
H77C H -0.0295 0.9152 0.3583 0.201 Uiso 1 1 calc R K 1
C78 C 0.1127(6) 0.9218(3) 0.4031(3) 0.124(2) Uani 1 1 d . K 1
H78A H 0.1312 0.9199 0.4405 0.148 Uiso 1 1 calc R K 1
H78B H 0.1443 0.8818 0.3871 0.148 Uiso 1 1 calc R K 1
C79 C 0.5850(5) 0.4311(3) 0.3982(2) 0.0972(19) Uani 1 1 d . I 1
H79A H 0.6112 0.4384 0.3633 0.146 Uiso 1 1 calc R I 1
H79B H 0.6197 0.3909 0.4126 0.146 Uiso 1 1 calc R I 1
H79C H 0.6059 0.4691 0.4199 0.146 Uiso 1 1 calc R I 1
C80 C 0.4575(4) 0.4233(2) 0.3962(2) 0.0743(14) Uani 1 1 d . I 1
H80A H 0.4351 0.3905 0.3695 0.089 Uiso 1 1 calc R I 1
H80B H 0.4325 0.4068 0.4298 0.089 Uiso 1 1 calc R I 1
C81 C 0.4629(6) 0.8676(3) 0.1319(3) 0.142(3) Uani 1 1 d . L 1
H81A H 0.4583 0.8752 0.1690 0.213 Uiso 1 1 calc R L 1
H81B H 0.4230 0.8268 0.1225 0.213 Uiso 1 1 calc R L 1
H81C H 0.4287 0.9050 0.1131 0.213 Uiso 1 1 calc R L 1
C82 C 0.5812(5) 0.8615(2) 0.1185(2) 0.0890(18) Uani 1 1 d . L 1
H82A H 0.6196 0.8315 0.1435 0.107 Uiso 1 1 calc R L 1
H82B H 0.5849 0.8410 0.0840 0.107 Uiso 1 1 calc R L 1
C83 C 1.0543(5) 0.3668(3) 0.1284(3) 0.132(3) Uani 1 1 d . J 1
H83A H 1.0854 0.4017 0.1069 0.198 Uiso 1 1 calc R J 1
H83B H 1.0926 0.3249 0.1218 0.198 Uiso 1 1 calc R J 1
H83C H 1.0653 0.3787 0.1648 0.198 Uiso 1 1 calc R J 1
C84 C 0.9330(5) 0.3595(2) 0.1159(2) 0.0864(16) Uani 1 1 d . J 1
H84A H 0.9226 0.3396 0.0812 0.104 Uiso 1 1 calc R J 1
H84B H 0.8996 0.3291 0.1410 0.104 Uiso 1 1 calc R J 1
C24 C 0.1698(4) 0.1613(2) 0.48451(17) 0.0622(12) Uani 1 1 d . F 1
C22 C 0.2312(5) 0.0980(3) 0.5067(2) 0.0951(17) Uani 1 1 d . F 1
H22A H 0.2195 0.0948 0.5438 0.143 Uiso 1 1 calc R F 1
H22B H 0.3116 0.1013 0.5008 0.143 Uiso 1 1 calc R F 1
H22C H 0.2007 0.0584 0.4894 0.143 Uiso 1 1 calc R F 1
C21 C 0.0445(5) 0.1617(3) 0.4987(2) 0.110(2) Uani 1 1 d . F 1
H21A H 0.0062 0.1237 0.4826 0.166 Uiso 1 1 calc R F 1
H21B H 0.0093 0.2028 0.4863 0.166 Uiso 1 1 calc R F 1
H21C H 0.0391 0.1589 0.5361 0.166 Uiso 1 1 calc R F 1
C23 C 0.2310(5) 0.2250(3) 0.5060(2) 0.0982(19) Uani 1 1 d . F 1
H23A H 0.2353 0.2232 0.5437 0.147 Uiso 1 1 calc R F 1
H23B H 0.1888 0.2644 0.4949 0.147 Uiso 1 1 calc R F 1
H23C H 0.3068 0.2271 0.4929 0.147 Uiso 1 1 calc R F 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.504(3) . ?
P1 O3 1.505(3) . ?
P1 O1 1.552(3) . ?
P1 C2 1.797(5) . ?
P2 O5 1.482(3) . ?
P2 O6 1.512(2) . ?
P2 O4 1.577(3) . ?
P2 C7 1.808(4) . ?
P3 O8 1.506(3) . ?
P3 O9 1.512(3) . ?
P3 O7 1.558(3) . ?
P3 C10 1.804(5) . ?
P4 O11 1.475(3) . ?
P4 O12 1.510(3) . ?
P4 O10 1.578(3) . ?
P4 C15 1.813(4) . ?
P5 O13 1.507(3) . ?
P5 O14 1.516(3) . ?
P5 O15 1.555(3) . ?
P5 C18 1.816(5) . ?
P6 O18 1.500(3) . ?
P6 O17 1.507(3) . ?
P6 O16 1.562(3) . ?
P6 C24 1.812(4) . ?
P7 O19 1.504(3) . ?
P7 O20 1.514(3) . ?
P7 O21 1.548(3) . ?
P7 C26 1.809(4) . ?
P8 O23 1.465(3) . ?
P8 O22 1.509(3) . ?
P8 O24 1.567(3) . ?
P8 C30 1.805(5) . ?
O1 H1E 0.8200 . ?
O4 H4E 0.8200 . ?
O7 H7E 0.8200 . ?
O10 H10E 0.8200 . ?
O15 H15E 0.8200 . ?
O16 H16E 0.8200 . ?
O21 H21E 0.8200 . ?
O24 H24E 0.8200 . ?
O25 C80 1.407(5) . ?
O25 H25E 0.8200 . ?
O26 C84 1.374(5) . ?
O26 H26E 0.8200 . ?
O27 C78 1.402(7) . ?
O27 H27E 0.8200 . ?
O28 C82 1.367(5) . ?
O28 H28E 0.8200 . ?
N1 N2 1.338(4) . ?
N1 C36 1.347(5) . ?
N1 H1D 0.8600 . ?
N2 C34 1.338(5) . ?
N2 H2D 0.8600 . ?
N3 C42 1.317(5) . ?
N3 N4 1.341(4) . ?
N3 H3D 0.8600 . ?
N4 C40 1.333(5) . ?
N4 H4D 0.8600 . ?
N5 C47 1.335(5) . ?
N5 N6 1.347(4) . ?
N5 H5D 0.8600 . ?
N6 C45 1.337(5) . ?
N6 H6D 0.8600 . ?
N7 N8 1.332(4) . ?
N7 C53 1.336(4) . ?
N7 H7D 0.8600 . ?
N8 C51 1.343(4) . ?
N8 H8D 0.8600 . ?
N9 C56 1.324(5) . ?
N9 N10 1.338(4) . ?
N9 H9D 0.8600 . ?
N10 C58 1.336(5) . ?
N10 H10D 0.8600 . ?
N11 C62 1.346(5) . ?
N11 N12 1.347(4) . ?
N11 H11D 0.8600 . ?
N12 C64 1.332(5) . ?
N12 H12D 0.8600 . ?
N13 C67 1.323(5) . ?
N13 N14 1.341(4) . ?
N13 H13D 0.8600 . ?
N14 C69 1.334(5) . ?
N14 H14D 0.8600 . ?
N15 C73 1.332(4) . ?
N15 N16 1.348(4) . ?
N15 H15D 0.8600 . ?
N16 C75 1.339(5) . ?
N16 H16D 0.8600 . ?
C1 C2 1.535(7) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1A 0.9600 . ?
C2 C4 1.520(8) . ?
C2 C3 1.558(8) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C7 1.538(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.527(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.531(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.541(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.514(8) . ?
C10 C12 1.556(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C15 1.524(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.523(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.538(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.547(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C20 1.517(8) . ?
C18 C19 1.533(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C25 C26 1.546(7) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C28 1.485(8) . ?
C26 C27 1.538(6) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.528(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C32 1.536(7) . ?
C30 C31 1.546(7) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.503(5) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.382(5) . ?
C35 C36 1.390(5) . ?
C35 C38 1.512(5) . ?
C36 C37 1.485(5) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C41 1.508(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.500(5) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 C41 1.367(5) . ?
C41 C42 1.394(5) . ?
C42 C43 1.501(6) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.479(5) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 C46 1.397(5) . ?
C46 C47 1.391(5) . ?
C46 C49 1.498(5) . ?
C47 C48 1.482(5) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C52 1.504(5) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 C51 1.498(5) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 C52 1.388(5) . ?
C52 C53 1.383(5) . ?
C53 C54 1.489(5) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C55 C56 1.493(5) . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C56 C57 1.394(5) . ?
C57 C58 1.373(5) . ?
C57 C60 1.508(5) . ?
C58 C59 1.507(5) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 C63 1.515(5) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C61 C62 1.487(5) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 C63 1.380(5) . ?
C63 C64 1.385(5) . ?
C64 C65 1.491(5) . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C66 C67 1.505(6) . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C67 C68 1.391(5) . ?
C68 C69 1.381(5) . ?
C68 C71 1.507(5) . ?
C69 C70 1.501(5) . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C71 C74 1.496(5) . ?
C71 H71A 0.9700 . ?
C71 H71B 0.9700 . ?
C72 C73 1.481(5) . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?
C73 C74 1.396(5) . ?
C74 C75 1.400(5) . ?
C75 C76 1.484(5) . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?
C77 C78 1.451(9) . ?
C77 H77A 0.9600 . ?
C77 H77B 0.9600 . ?
C77 H77C 0.9600 . ?
C78 H78A 0.9700 . ?
C78 H78B 0.9700 . ?
C79 C80 1.499(7) . ?
C79 H79A 0.9600 . ?
C79 H79B 0.9600 . ?
C79 H79C 0.9600 . ?
C80 H80A 0.9700 . ?
C80 H80B 0.9700 . ?
C81 C82 1.442(8) . ?
C81 H81A 0.9600 . ?
C81 H81B 0.9600 . ?
C81 H81C 0.9600 . ?
C82 H82A 0.9700 . ?
C82 H82B 0.9700 . ?
C83 C84 1.451(7) . ?
C83 H83A 0.9600 . ?
C83 H83B 0.9600 . ?
C83 H83C 0.9600 . ?
C84 H84A 0.9700 . ?
C84 H84B 0.9700 . ?
C24 C21 1.522(7) . ?
C24 C23 1.542(6) . ?
C24 C22 1.542(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O2 P1 O3 112.95(15) . . ?
O2 P1 O1 110.47(16) . . ?
O3 P1 O1 106.66(16) . . ?
O2 P1 C2 108.6(2) . . ?
O3 P1 C2 109.36(18) . . ?
O1 P1 C2 108.8(2) . . ?
O5 P2 O6 115.29(17) . . ?
O5 P2 O4 109.46(17) . . ?
O6 P2 O4 105.65(14) . . ?
O5 P2 C7 110.19(19) . . ?
O6 P2 C7 109.67(17) . . ?
O4 P2 C7 106.10(18) . . ?
O8 P3 O9 112.64(15) . . ?
O8 P3 O7 111.00(17) . . ?
O9 P3 O7 106.72(15) . . ?
O8 P3 C10 108.6(2) . . ?
O9 P3 C10 109.27(18) . . ?
O7 P3 C10 108.5(2) . . ?
O11 P4 O12 115.17(16) . . ?
O11 P4 O10 109.63(16) . . ?
O12 P4 O10 106.10(14) . . ?
O11 P4 C15 110.49(18) . . ?
O12 P4 C15 109.36(16) . . ?
O10 P4 C15 105.57(18) . . ?
O13 P5 O14 112.05(15) . . ?
O13 P5 O15 107.81(16) . . ?
O14 P5 O15 111.00(16) . . ?
O13 P5 C18 110.27(19) . . ?
O14 P5 C18 108.4(2) . . ?
O15 P5 C18 107.2(2) . . ?
O18 P6 O17 117.14(18) . . ?
O18 P6 O16 111.78(18) . . ?
O17 P6 O16 104.01(15) . . ?
O18 P6 C24 107.68(19) . . ?
O17 P6 C24 109.98(19) . . ?
O16 P6 C24 105.7(2) . . ?
O19 P7 O20 111.94(16) . . ?
O19 P7 O21 107.35(16) . . ?
O20 P7 O21 111.28(16) . . ?
O19 P7 C26 110.03(18) . . ?
O20 P7 C26 108.9(2) . . ?
O21 P7 C26 107.3(2) . . ?
O23 P8 O22 116.5(2) . . ?
O23 P8 O24 110.28(18) . . ?
O22 P8 O24 105.36(17) . . ?
O23 P8 C30 108.0(2) . . ?
O22 P8 C30 109.59(18) . . ?
O24 P8 C30 106.7(2) . . ?
N2 N1 C36 108.6(3) . . ?
N2 N1 H1D 125.7 . . ?
C36 N1 H1D 125.7 . . ?
C34 N2 N1 109.2(3) . . ?
C34 N2 H2D 125.4 . . ?
N1 N2 H2D 125.4 . . ?
C42 N3 N4 108.0(3) . . ?
C42 N3 H3D 126.0 . . ?
N4 N3 H3D 126.0 . . ?
C40 N4 N3 109.7(4) . . ?
C40 N4 H4D 125.1 . . ?
N3 N4 H4D 125.1 . . ?
C47 N5 N6 108.8(3) . . ?
C47 N5 H5D 125.6 . . ?
N6 N5 H5D 125.6 . . ?
C45 N6 N5 109.7(3) . . ?
C45 N6 H6D 125.2 . . ?
N5 N6 H6D 125.2 . . ?
N8 N7 C53 109.2(3) . . ?
N8 N7 H7D 125.4 . . ?
C53 N7 H7D 125.4 . . ?
N7 N8 C51 109.3(3) . . ?
N7 N8 H8D 125.4 . . ?
C51 N8 H8D 125.4 . . ?
C56 N9 N10 107.9(3) . . ?
C56 N9 H9D 126.1 . . ?
N10 N9 H9D 126.1 . . ?
C58 N10 N9 110.2(3) . . ?
C58 N10 H10D 124.9 . . ?
N9 N10 H10D 124.9 . . ?
C62 N11 N12 107.8(3) . . ?
C62 N11 H11D 126.1 . . ?
N12 N11 H11D 126.1 . . ?
C64 N12 N11 109.9(3) . . ?
C64 N12 H12D 125.0 . . ?
N11 N12 H12D 125.0 . . ?
C67 N13 N14 108.1(3) . . ?
C67 N13 H13D 126.0 . . ?
N14 N13 H13D 126.0 . . ?
C69 N14 N13 109.6(3) . . ?
C69 N14 H14D 125.2 . . ?
N13 N14 H14D 125.2 . . ?
C73 N15 N16 109.0(3) . . ?
C73 N15 H15D 125.5 . . ?
N16 N15 H15D 125.5 . . ?
C75 N16 N15 109.3(3) . . ?
C75 N16 H16D 125.3 . . ?
N15 N16 H16D 125.3 . . ?
C4 C2 C1 108.3(4) . . ?
C4 C2 C3 111.9(5) . . ?
C1 C2 C3 108.8(5) . . ?
C4 C2 P1 109.1(4) . . ?
C1 C2 P1 110.7(3) . . ?
C3 C2 P1 107.9(4) . . ?
C6 C7 C8 108.5(4) . . ?
C6 C7 C5 110.0(4) . . ?
C8 C7 C5 112.1(4) . . ?
C6 C7 P2 108.9(3) . . ?
C8 C7 P2 108.0(3) . . ?
C5 C7 P2 109.3(3) . . ?
C11 C10 C9 110.6(5) . . ?
C11 C10 C12 112.1(5) . . ?
C9 C10 C12 108.1(5) . . ?
C11 C10 P3 107.9(4) . . ?
C9 C10 P3 110.4(3) . . ?
C12 C10 P3 107.7(5) . . ?
C14 C15 C13 110.4(4) . . ?
C14 C15 C16 108.5(4) . . ?
C13 C15 C16 111.0(4) . . ?
C14 C15 P4 108.1(3) . . ?
C13 C15 P4 110.5(3) . . ?
C16 C15 P4 108.2(3) . . ?
C20 C18 C19 109.9(5) . . ?
C20 C18 C17 110.5(5) . . ?
C19 C18 C17 108.8(5) . . ?
C20 C18 P5 108.8(4) . . ?
C19 C18 P5 109.9(3) . . ?
C17 C18 P5 108.9(4) . . ?
C28 C26 C27 111.9(5) . . ?
C28 C26 C25 108.4(5) . . ?
C27 C26 C25 107.7(4) . . ?
C28 C26 P7 109.6(4) . . ?
C27 C26 P7 109.8(3) . . ?
C25 C26 P7 109.4(3) . . ?
C29 C30 C32 110.5(4) . . ?
C29 C30 C31 108.1(4) . . ?
C32 C30 C31 110.8(5) . . ?
C29 C30 P8 109.6(3) . . ?
C32 C30 P8 109.8(4) . . ?
C31 C30 P8 108.1(4) . . ?
N2 C34 C35 108.6(3) . . ?
N2 C34 C33 121.2(3) . . ?
C35 C34 C33 130.2(3) . . ?
C34 C35 C36 105.5(3) . . ?
C34 C35 C38 128.0(4) . . ?
C36 C35 C38 126.5(3) . . ?
N1 C36 C35 108.2(3) . . ?
N1 C36 C37 120.9(4) . . ?
C35 C36 C37 131.0(4) . . ?
C41 C38 C35 114.6(3) . . ?
C41 C38 H38A 108.6 . . ?
C35 C38 H38A 108.6 . . ?
C41 C38 H38B 108.6 . . ?
C35 C38 H38B 108.6 . . ?
H38A C38 H38B 107.6 . . ?
N4 C40 C41 107.8(3) . . ?
N4 C40 C39 121.1(4) . . ?
C41 C40 C39 131.1(4) . . ?
C40 C41 C42 105.6(4) . . ?
C40 C41 C38 127.7(3) . . ?
C42 C41 C38 126.7(4) . . ?
N3 C42 C41 108.8(4) . . ?
N3 C42 C43 121.2(4) . . ?
C41 C42 C43 130.0(4) . . ?
N6 C45 C46 107.3(3) . . ?
N6 C45 C44 121.6(3) . . ?
C46 C45 C44 131.0(4) . . ?
C47 C46 C45 106.0(3) . . ?
C47 C46 C49 126.8(3) . . ?
C45 C46 C49 127.2(4) . . ?
N5 C47 C46 108.1(3) . . ?
N5 C47 C48 121.2(4) . . ?
C46 C47 C48 130.6(4) . . ?
C46 C49 C52 114.0(3) . . ?
C46 C49 H49A 108.8 . . ?
C52 C49 H49A 108.8 . . ?
C46 C49 H49B 108.8 . . ?
C52 C49 H49B 108.8 . . ?
H49A C49 H49B 107.6 . . ?
N8 C51 C52 107.4(3) . . ?
N8 C51 C50 121.7(3) . . ?
C52 C51 C50 130.9(3) . . ?
C53 C52 C51 106.1(3) . . ?
C53 C52 C49 127.3(3) . . ?
C51 C52 C49 126.5(3) . . ?
N7 C53 C52 108.0(3) . . ?
N7 C53 C54 121.0(3) . . ?
C52 C53 C54 131.0(3) . . ?
N9 C56 C57 108.8(3) . . ?
N9 C56 C55 120.6(3) . . ?
C57 C56 C55 130.6(3) . . ?
C58 C57 C56 105.7(3) . . ?
C58 C57 C60 128.1(3) . . ?
C56 C57 C60 126.2(3) . . ?
N10 C58 C57 107.5(3) . . ?
N10 C58 C59 121.3(3) . . ?
C57 C58 C59 131.2(3) . . ?
C57 C60 C63 113.7(3) . . ?
C57 C60 H60A 108.8 . . ?
C63 C60 H60A 108.8 . . ?
C57 C60 H60B 108.8 . . ?
C63 C60 H60B 108.8 . . ?
H60A C60 H60B 107.7 . . ?
N11 C62 C63 108.4(3) . . ?
N11 C62 C61 120.7(4) . . ?
C63 C62 C61 130.9(4) . . ?
C62 C63 C64 106.3(3) . . ?
C62 C63 C60 126.4(3) . . ?
C64 C63 C60 127.3(4) . . ?
N12 C64 C63 107.6(3) . . ?
N12 C64 C65 121.6(3) . . ?
C63 C64 C65 130.8(4) . . ?
N13 C67 C68 109.2(3) . . ?
N13 C67 C66 121.2(4) . . ?
C68 C67 C66 129.5(4) . . ?
C69 C68 C67 105.0(3) . . ?
C69 C68 C71 127.3(3) . . ?
C67 C68 C71 127.6(4) . . ?
N14 C69 C68 108.1(3) . . ?
N14 C69 C70 121.8(4) . . ?
C68 C69 C70 130.2(4) . . ?
C74 C71 C68 113.7(3) . . ?
C74 C71 H71A 108.8 . . ?
C68 C71 H71A 108.8 . . ?
C74 C71 H71B 108.8 . . ?
C68 C71 H71B 108.8 . . ?
H71A C71 H71B 107.7 . . ?
N15 C73 C74 108.4(3) . . ?
N15 C73 C72 121.1(3) . . ?
C74 C73 C72 130.5(3) . . ?
C73 C74 C75 105.4(3) . . ?
C73 C74 C71 127.6(3) . . ?
C75 C74 C71 127.0(3) . . ?
N16 C75 C74 107.8(3) . . ?
N16 C75 C76 121.0(3) . . ?
C74 C75 C76 131.3(4) . . ?
O27 C78 C77 112.6(5) . . ?
O27 C78 H78A 109.1 . . ?
C77 C78 H78A 109.1 . . ?
O27 C78 H78B 109.1 . . ?
C77 C78 H78B 109.1 . . ?
H78A C78 H78B 107.8 . . ?
O25 C80 C79 110.1(4) . . ?
O25 C80 H80A 109.6 . . ?
C79 C80 H80A 109.6 . . ?
O25 C80 H80B 109.6 . . ?
C79 C80 H80B 109.6 . . ?
H80A C80 H80B 108.1 . . ?
O28 C82 C81 113.8(5) . . ?
O28 C82 H82A 108.8 . . ?
C81 C82 H82A 108.8 . . ?
O28 C82 H82B 108.8 . . ?
C81 C82 H82B 108.8 . . ?
H82A C82 H82B 107.7 . . ?
O26 C84 C83 111.5(4) . . ?
O26 C84 H84A 109.3 . . ?
C83 C84 H84A 109.3 . . ?
O26 C84 H84B 109.3 . . ?
C83 C84 H84B 109.3 . . ?
H84A C84 H84B 108.0 . . ?
C21 C24 C23 110.4(4) . . ?
C21 C24 C22 111.0(4) . . ?
C23 C24 C22 109.3(4) . . ?
C21 C24 P6 108.8(3) . . ?
C23 C24 P6 108.4(3) . . ?
C22 C24 P6 108.9(3) . . ?

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
C36 N1 N2 C34 -1.5(4) . . . . ?
C42 N3 N4 C40 -1.1(5) . . . . ?
C47 N5 N6 C45 1.6(4) . . . . ?
C53 N7 N8 C51 0.8(4) . . . . ?
C56 N9 N10 C58 0.1(5) . . . . ?
C62 N11 N12 C64 1.6(4) . . . . ?
C67 N13 N14 C69 0.7(4) . . . . ?
C73 N15 N16 C75 -2.0(4) . . . . ?
O2 P1 C2 C4 177.6(4) . . . . ?
O3 P1 C2 C4 -58.7(4) . . . . ?
O1 P1 C2 C4 57.4(4) . . . . ?
O2 P1 C2 C1 58.5(4) . . . . ?
O3 P1 C2 C1 -177.9(4) . . . . ?
O1 P1 C2 C1 -61.8(5) . . . . ?
O2 P1 C2 C3 -60.6(4) . . . . ?
O3 P1 C2 C3 63.1(5) . . . . ?
O1 P1 C2 C3 179.2(4) . . . . ?
O5 P2 C7 C6 -55.0(4) . . . . ?
O6 P2 C7 C6 177.1(3) . . . . ?
O4 P2 C7 C6 63.4(3) . . . . ?
O5 P2 C7 C8 62.7(4) . . . . ?
O6 P2 C7 C8 -65.3(4) . . . . ?
O4 P2 C7 C8 -178.9(3) . . . . ?
O5 P2 C7 C5 -175.1(3) . . . . ?
O6 P2 C7 C5 56.9(4) . . . . ?
O4 P2 C7 C5 -56.7(4) . . . . ?
O8 P3 C10 C11 62.2(5) . . . . ?
O9 P3 C10 C11 -61.1(5) . . . . ?
O7 P3 C10 C11 -177.1(4) . . . . ?
O8 P3 C10 C9 -58.8(5) . . . . ?
O9 P3 C10 C9 177.9(4) . . . . ?
O7 P3 C10 C9 62.0(5) . . . . ?
O8 P3 C10 C12 -176.6(4) . . . . ?
O9 P3 C10 C12 60.1(4) . . . . ?
O7 P3 C10 C12 -55.8(4) . . . . ?
O11 P4 C15 C14 54.5(3) . . . . ?
O12 P4 C15 C14 -177.8(3) . . . . ?
O10 P4 C15 C14 -64.0(3) . . . . ?
O11 P4 C15 C13 175.4(3) . . . . ?
O12 P4 C15 C13 -56.8(4) . . . . ?
O10 P4 C15 C13 57.0(3) . . . . ?
O11 P4 C15 C16 -62.9(3) . . . . ?
O12 P4 C15 C16 64.9(3) . . . . ?
O10 P4 C15 C16 178.7(3) . . . . ?
O13 P5 C18 C20 -57.5(4) . . . . ?
O14 P5 C18 C20 179.5(4) . . . . ?
O15 P5 C18 C20 59.6(4) . . . . ?
O13 P5 C18 C19 -178.0(3) . . . . ?
O14 P5 C18 C19 59.1(4) . . . . ?
O15 P5 C18 C19 -60.8(4) . . . . ?
O13 P5 C18 C17 62.9(5) . . . . ?
O14 P5 C18 C17 -60.0(4) . . . . ?
O15 P5 C18 C17 -179.9(4) . . . . ?
O19 P7 C26 C28 49.7(4) . . . . ?
O20 P7 C26 C28 172.7(4) . . . . ?
O21 P7 C26 C28 -66.7(4) . . . . ?
O19 P7 C26 C27 173.1(4) . . . . ?
O20 P7 C26 C27 -63.9(4) . . . . ?
O21 P7 C26 C27 56.6(4) . . . . ?
O19 P7 C26 C25 -68.9(4) . . . . ?
O20 P7 C26 C25 54.1(4) . . . . ?
O21 P7 C26 C25 174.6(3) . . . . ?
O23 P8 C30 C29 -64.9(4) . . . . ?
O22 P8 C30 C29 62.9(4) . . . . ?
O24 P8 C30 C29 176.5(3) . . . . ?
O23 P8 C30 C32 173.6(4) . . . . ?
O22 P8 C30 C32 -58.6(4) . . . . ?
O24 P8 C30 C32 55.0(4) . . . . ?
O23 P8 C30 C31 52.6(4) . . . . ?
O22 P8 C30 C31 -179.5(3) . . . . ?
O24 P8 C30 C31 -65.9(4) . . . . ?
N1 N2 C34 C35 1.4(5) . . . . ?
N1 N2 C34 C33 -177.5(3) . . . . ?
N2 C34 C35 C36 -0.8(5) . . . . ?
C33 C34 C35 C36 178.0(4) . . . . ?
N2 C34 C35 C38 179.1(4) . . . . ?
C33 C34 C35 C38 -2.2(7) . . . . ?
N2 N1 C36 C35 1.0(4) . . . . ?
N2 N1 C36 C37 -179.5(4) . . . . ?
C34 C35 C36 N1 -0.1(5) . . . . ?
C38 C35 C36 N1 -180.0(4) . . . . ?
C34 C35 C36 C37 -179.6(4) . . . . ?
C38 C35 C36 C37 0.6(7) . . . . ?
C34 C35 C38 C41 120.7(4) . . . . ?
C36 C35 C38 C41 -59.5(5) . . . . ?
N3 N4 C40 C41 0.2(4) . . . . ?
N3 N4 C40 C39 -179.5(3) . . . . ?
N4 C40 C41 C42 0.8(4) . . . . ?
C39 C40 C41 C42 -179.6(4) . . . . ?
N4 C40 C41 C38 -177.6(3) . . . . ?
C39 C40 C41 C38 2.1(7) . . . . ?
C35 C38 C41 C40 -62.6(5) . . . . ?
C35 C38 C41 C42 119.3(4) . . . . ?
N4 N3 C42 C41 1.6(5) . . . . ?
N4 N3 C42 C43 -178.9(4) . . . . ?
C40 C41 C42 N3 -1.5(5) . . . . ?
C38 C41 C42 N3 176.9(3) . . . . ?
C40 C41 C42 C43 179.1(5) . . . . ?
C38 C41 C42 C43 -2.5(7) . . . . ?
N5 N6 C45 C46 -1.3(4) . . . . ?
N5 N6 C45 C44 178.2(3) . . . . ?
N6 C45 C46 C47 0.6(4) . . . . ?
C44 C45 C46 C47 -178.9(4) . . . . ?
N6 C45 C46 C49 -178.6(3) . . . . ?
C44 C45 C46 C49 2.0(6) . . . . ?
N6 N5 C47 C46 -1.2(4) . . . . ?
N6 N5 C47 C48 179.7(3) . . . . ?
C45 C46 C47 N5 0.4(4) . . . . ?
C49 C46 C47 N5 179.5(3) . . . . ?
C45 C46 C47 C48 179.4(4) . . . . ?
C49 C46 C47 C48 -1.4(6) . . . . ?
C47 C46 C49 C52 63.0(5) . . . . ?
C45 C46 C49 C52 -118.0(4) . . . . ?
N7 N8 C51 C52 0.1(4) . . . . ?
N7 N8 C51 C50 -179.3(4) . . . . ?
N8 C51 C52 C53 -0.9(5) . . . . ?
C50 C51 C52 C53 178.4(4) . . . . ?
N8 C51 C52 C49 178.8(4) . . . . ?
C50 C51 C52 C49 -1.9(7) . . . . ?
C46 C49 C52 C53 -123.0(4) . . . . ?
C46 C49 C52 C51 57.4(5) . . . . ?
N8 N7 C53 C52 -1.4(5) . . . . ?
N8 N7 C53 C54 179.0(4) . . . . ?
C51 C52 C53 N7 1.4(5) . . . . ?
C49 C52 C53 N7 -178.3(4) . . . . ?
C51 C52 C53 C54 -179.0(4) . . . . ?
C49 C52 C53 C54 1.3(8) . . . . ?
N10 N9 C56 C57 -0.4(5) . . . . ?
N10 N9 C56 C55 178.5(4) . . . . ?
N9 C56 C57 C58 0.6(5) . . . . ?
C55 C56 C57 C58 -178.3(5) . . . . ?
N9 C56 C57 C60 -177.2(4) . . . . ?
C55 C56 C57 C60 4.0(7) . . . . ?
N9 N10 C58 C57 0.2(5) . . . . ?
N9 N10 C58 C59 -179.2(4) . . . . ?
C56 C57 C58 N10 -0.5(5) . . . . ?
C60 C57 C58 N10 177.2(4) . . . . ?
C56 C57 C58 C59 178.8(4) . . . . ?
C60 C57 C58 C59 -3.5(8) . . . . ?
C58 C57 C60 C63 61.2(6) . . . . ?
C56 C57 C60 C63 -121.6(4) . . . . ?
N12 N11 C62 C63 -1.4(4) . . . . ?
N12 N11 C62 C61 179.7(3) . . . . ?
N11 C62 C63 C64 0.8(4) . . . . ?
C61 C62 C63 C64 179.5(4) . . . . ?
N11 C62 C63 C60 179.6(3) . . . . ?
C61 C62 C63 C60 -1.7(6) . . . . ?
C57 C60 C63 C62 64.3(5) . . . . ?
C57 C60 C63 C64 -117.1(4) . . . . ?
N11 N12 C64 C63 -1.1(4) . . . . ?
N11 N12 C64 C65 177.4(3) . . . . ?
C62 C63 C64 N12 0.2(4) . . . . ?
C60 C63 C64 N12 -178.7(3) . . . . ?
C62 C63 C64 C65 -178.2(4) . . . . ?
C60 C63 C64 C65 3.0(6) . . . . ?
N14 N13 C67 C68 -0.3(4) . . . . ?
N14 N13 C67 C66 -178.8(3) . . . . ?
N13 C67 C68 C69 -0.1(4) . . . . ?
C66 C67 C68 C69 178.1(4) . . . . ?
N13 C67 C68 C71 178.3(3) . . . . ?
C66 C67 C68 C71 -3.5(6) . . . . ?
N13 N14 C69 C68 -0.8(4) . . . . ?
N13 N14 C69 C70 179.0(3) . . . . ?
C67 C68 C69 N14 0.6(4) . . . . ?
C71 C68 C69 N14 -177.8(3) . . . . ?
C67 C68 C69 C70 -179.3(4) . . . . ?
C71 C68 C69 C70 2.3(6) . . . . ?
C69 C68 C71 C74 -59.3(5) . . . . ?
C67 C68 C71 C74 122.7(4) . . . . ?
N16 N15 C73 C74 0.8(4) . . . . ?
N16 N15 C73 C72 -178.7(3) . . . . ?
N15 C73 C74 C75 0.6(4) . . . . ?
C72 C73 C74 C75 180.0(4) . . . . ?
N15 C73 C74 C71 179.8(4) . . . . ?
C72 C73 C74 C71 -0.8(7) . . . . ?
C68 C71 C74 C73 -61.6(5) . . . . ?
C68 C71 C74 C75 117.4(4) . . . . ?
N15 N16 C75 C74 2.3(4) . . . . ?
N15 N16 C75 C76 -177.6(4) . . . . ?
C73 C74 C75 N16 -1.8(4) . . . . ?
C71 C74 C75 N16 179.0(4) . . . . ?
C73 C74 C75 C76 178.2(4) . . . . ?
C71 C74 C75 C76 -1.0(7) . . . . ?
O18 P6 C24 C21 -170.7(3) . . . . ?
O17 P6 C24 C21 60.5(4) . . . . ?
O16 P6 C24 C21 -51.1(4) . . . . ?
O18 P6 C24 C23 69.1(3) . . . . ?
O17 P6 C24 C23 -59.6(4) . . . . ?
O16 P6 C24 C23 -171.3(3) . . . . ?
O18 P6 C24 C22 -49.7(4) . . . . ?
O17 P6 C24 C22 -178.4(3) . . . . ?
O16 P6 C24 C22 69.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 980601'
