# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_m24
_database_code_depnum_ccdc_archive 'CCDC 989375'
_audit_update_record             
;
2014-03-01 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 N4 O6 P'
_chemical_formula_sum            'C10 H15 N4 O6 P'
_chemical_formula_weight         318.23

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 b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   8.8012(5)
_cell_length_b                   13.0262(8)
_cell_length_c                   25.0491(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2871.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1214
_cell_measurement_theta_min      3
_cell_measurement_theta_max      29

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   SADABS

_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  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11086
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3791
_reflns_number_gt                3157
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0460P)²+1.1411P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3791
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.04617(4) 0.04465(2) 0.683514(13) 0.01217(9) Uani 1 1 d . . .
O1 O -0.11044(10) 0.07284(7) 0.69910(4) 0.0154(2) Uani 1 1 d . . .
O2 O 0.06507(11) 0.00371(7) 0.62438(4) 0.0166(2) Uani 1 1 d . . .
O3 O -0.08190(10) -0.14232(7) 0.78699(4) 0.0171(2) Uani 1 1 d . . .
O4 O 0.06249(11) -0.07307(8) 0.85312(4) 0.0208(2) Uani 1 1 d . . .
O5 O 0.35552(11) 0.23834(9) 0.62239(4) 0.0241(2) Uani 1 1 d . . .
O6 O 0.54400(10) 0.18815(8) 0.67868(4) 0.0196(2) Uani 1 1 d . . .
N1 N 0.11636(13) -0.05643(8) 0.71448(5) 0.0146(2) Uani 1 1 d . . .
H1N H 0.1938 -0.0910 0.7009 0.024(4) Uiso 1 1 d R . .
N2 N 0.12896(13) -0.04464(9) 0.76987(5) 0.0159(2) Uani 1 1 d . . .
H2N H 0.2064 -0.0118 0.7832 0.020(4) Uiso 1 1 d R . .
N3 N 0.15396(12) 0.14511(8) 0.69243(5) 0.0154(2) Uani 1 1 d . . .
H3N H 0.1204 0.2022 0.7043 0.026(5) Uiso 1 1 d R . .
N4 N 0.31236(12) 0.13418(9) 0.69499(5) 0.0165(2) Uani 1 1 d . . .
H4N H 0.3508 0.1226 0.7276 0.025(5) Uiso 1 1 d R . .
C1 C -0.00735(16) 0.05675(10) 0.58202(5) 0.0167(3) Uani 1 1 d . . .
C2 C -0.16237(17) 0.04596(12) 0.57519(6) 0.0236(3) Uani 1 1 d . . .
H2 H -0.2270 -0.0042 0.6010 0.044(6) Uiso 1 1 d R . .
C3 C -0.23084(19) 0.09561(14) 0.53197(6) 0.0302(4) Uani 1 1 d . . .
H3 H -0.3524 0.0879 0.5277 0.056(7) Uiso 1 1 d R . .
C4 C -0.1450(2) 0.15304(13) 0.49673(6) 0.0303(4) Uani 1 1 d . . .
H4 H -0.1981 0.1898 0.4629 0.038(5) Uiso 1 1 d R . .
C5 C 0.0100(2) 0.16253(13) 0.50467(6) 0.0312(4) Uani 1 1 d . . .
H5 H 0.0845 0.2037 0.4779 0.041(6) Uiso 1 1 d R . .
C6 C 0.08091(18) 0.11472(12) 0.54791(6) 0.0254(3) Uani 1 1 d . . .
H6 H 0.2015 0.1184 0.5557 0.047(6) Uiso 1 1 d R . .
C7 C 0.02676(14) -0.09138(10) 0.80167(5) 0.0145(2) Uani 1 1 d . . .
C8 C -0.04166(19) -0.11444(14) 0.89224(6) 0.0298(4) Uani 1 1 d . . .
H8C H -0.1390 -0.0782 0.8898 0.045 Uiso 1 1 calc R . .
H8B H 0.0010 -0.1054 0.9281 0.045 Uiso 1 1 calc R . .
H8A H -0.0575 -0.1877 0.8853 0.045 Uiso 1 1 calc R . .
C9 C 0.39951(15) 0.19249(10) 0.66121(5) 0.0152(3) Uani 1 1 d . . .
C10 C 0.65026(15) 0.25516(11) 0.65195(6) 0.0229(3) Uani 1 1 d . . .
H10C H 0.6444 0.2439 0.6133 0.034 Uiso 1 1 calc R . .
H10B H 0.7535 0.2403 0.6644 0.034 Uiso 1 1 calc R . .
H10A H 0.6250 0.3268 0.6600 0.034 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 O1 1.4788(9) . ?
P1 O2 1.5831(10) . ?
P1 N3 1.6316(11) . ?
P1 N1 1.6484(11) . ?
O2 C1 1.4175(16) . ?
O3 C7 1.2207(16) . ?
O4 C7 1.3479(17) . ?
O4 C8 1.4458(18) . ?
O5 C9 1.2050(17) . ?
O6 C9 1.3461(15) . ?
O6 C10 1.4439(16) . ?
N1 N2 1.4003(16) . ?
N1 H1N 0.8852 . ?
N2 C7 1.3470(17) . ?
N2 H2N 0.8714 . ?
N3 N4 1.4029(15) . ?
N3 H3N 0.8535 . ?
N4 C9 1.3716(17) . ?
N4 H4N 0.8958 . ?
C1 C6 1.380(2) . ?
C1 C2 1.382(2) . ?
C2 C3 1.397(2) . ?
C2 H2 1.0801 . ?
C3 C4 1.382(2) . ?
C3 H3 1.0800 . ?
C4 C5 1.384(3) . ?
C4 H4 1.0802 . ?
C5 C6 1.397(2) . ?
C5 H5 1.0799 . ?
C6 H6 1.0800 . ?
C8 H8C 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8A 0.9800 . ?
C10 H10C 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 115.38(5) . . ?
O1 P1 N3 107.86(6) . . ?
O2 P1 N3 109.70(6) . . ?
O1 P1 N1 115.05(6) . . ?
O2 P1 N1 97.58(5) . . ?
N3 P1 N1 111.00(6) . . ?
C1 O2 P1 119.27(8) . . ?
C7 O4 C8 115.72(11) . . ?
C9 O6 C10 115.83(11) . . ?
N2 N1 P1 114.10(9) . . ?
N2 N1 H1N 112.1 . . ?
P1 N1 H1N 120.9 . . ?
C7 N2 N1 118.92(11) . . ?
C7 N2 H2N 121.1 . . ?
N1 N2 H2N 119.7 . . ?
N4 N3 P1 120.18(9) . . ?
N4 N3 H3N 114.6 . . ?
P1 N3 H3N 123.0 . . ?
C9 N4 N3 118.11(11) . . ?
C9 N4 H4N 116.4 . . ?
N3 N4 H4N 115.7 . . ?
C6 C1 C2 122.31(14) . . ?
C6 C1 O2 118.50(13) . . ?
C2 C1 O2 119.15(12) . . ?
C1 C2 C3 118.33(14) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.62(15) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 117.4 . . ?
C3 C4 C5 119.71(15) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.79(15) . . ?
C4 C5 H5 123.6 . . ?
C6 C5 H5 115.6 . . ?
C1 C6 C5 118.22(15) . . ?
C1 C6 H6 117.8 . . ?
C5 C6 H6 123.9 . . ?
O3 C7 N2 126.20(13) . . ?
O3 C7 O4 124.55(12) . . ?
N2 C7 O4 109.25(11) . . ?
O4 C8 H8C 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
O4 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
O5 C9 O6 125.93(12) . . ?
O5 C9 N4 126.35(12) . . ?
O6 C9 N4 107.72(11) . . ?
O6 C10 H10C 109.5 . . ?
O6 C10 H10B 109.5 . . ?
H10C C10 H10B 109.5 . . ?
O6 C10 H10A 109.5 . . ?
H10C C10 H10A 109.5 . . ?
H10B C10 H10A 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
O1 P1 O2 C1 45.54(11) . . . . ?
N3 P1 O2 C1 -76.49(11) . . . . ?
N1 P1 O2 C1 167.94(10) . . . . ?
O1 P1 N1 N2 -62.03(10) . . . . ?
O2 P1 N1 N2 175.33(9) . . . . ?
N3 P1 N1 N2 60.79(10) . . . . ?
P1 N1 N2 C7 103.88(12) . . . . ?
O1 P1 N3 N4 162.60(10) . . . . ?
O2 P1 N3 N4 -70.98(11) . . . . ?
N1 P1 N3 N4 35.72(12) . . . . ?
P1 N3 N4 C9 125.98(11) . . . . ?
P1 O2 C1 C6 106.75(13) . . . . ?
P1 O2 C1 C2 -75.43(15) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
O2 C1 C2 C3 -177.54(13) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
O2 C1 C6 C5 176.78(13) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
N1 N2 C7 O3 -2.3(2) . . . . ?
N1 N2 C7 O4 177.92(10) . . . . ?
C8 O4 C7 O3 -2.68(19) . . . . ?
C8 O4 C7 N2 177.15(12) . . . . ?
C10 O6 C9 O5 8.2(2) . . . . ?
C10 O6 C9 N4 -172.70(12) . . . . ?
N3 N4 C9 O5 -15.1(2) . . . . ?
N3 N4 C9 O6 165.82(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N(1) H(1N) O(3) 6_657 0.88 2.11 2.8820(14) 146 ?
N(2) H(2N) O(1) 6_657 0.87 2.00 2.8647(15) 170 ?
N(3) H(3N) O(3) 3_556 0.85 2.07 2.8871(14) 161 ?
N(4) H(4N) O(1) 6_657 0.90 1.98 2.8528(16) 165 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_m25
_database_code_depnum_ccdc_archive 'CCDC 989376'
_audit_update_record             
;
2014-03-01 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N2 O5 P'
_chemical_formula_sum            'C14 H15 N2 O5 P'
_chemical_formula_weight         322.25

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7570(2)
_cell_length_b                   8.9928(3)
_cell_length_c                   14.7059(6)
_cell_angle_alpha                78.9900(10)
_cell_angle_beta                 86.5040(10)
_cell_angle_gamma                87.8060(10)
_cell_volume                     745.67(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1409
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   SADABS

_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  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8958
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4327
_reflns_number_gt                4062
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0511P)²+0.3335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4327
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.63706(4) 0.43503(3) 0.289927(16) 0.01149(7) Uani 1 1 d . . .
O1 O 0.86113(12) 0.51136(9) 0.27305(5) 0.01604(15) Uani 1 1 d . . .
O2 O 0.50668(13) 0.42933(8) 0.19839(5) 0.01429(14) Uani 1 1 d . . .
O3 O 0.63893(13) 0.26133(8) 0.33538(5) 0.01527(14) Uani 1 1 d . . .
O4 O 0.36624(13) 0.30958(9) 0.52203(5) 0.01691(15) Uani 1 1 d . . .
O5 O -0.00323(13) 0.30274(10) 0.47672(6) 0.02211(17) Uani 1 1 d . . .
N1 N 0.45786(14) 0.51571(10) 0.35723(6) 0.01393(16) Uani 1 1 d . . .
H1N H 0.5078 0.5718 0.3915 0.027(4) Uiso 1 1 d R . .
N2 N 0.24300(15) 0.45004(10) 0.38540(6) 0.01579(17) Uani 1 1 d . . .
H2N H 0.1290 0.4815 0.3530 0.024(4) Uiso 1 1 d R . .
C1 C 0.50637(17) 0.55642(11) 0.12572(7) 0.01329(17) Uani 1 1 d . . .
C2 C 0.69885(18) 0.58008(12) 0.06375(7) 0.01574(18) Uani 1 1 d . . .
H2 H 0.8531 0.5075 0.0713 0.026(4) Uiso 1 1 d R . .
C3 C 0.69093(19) 0.70113(12) -0.01097(7) 0.0187(2) Uani 1 1 d . . .
H3 H 0.8389 0.7224 -0.0600 0.026(4) Uiso 1 1 d R . .
C4 C 0.4940(2) 0.79589(12) -0.02282(7) 0.0196(2) Uani 1 1 d . . .
H4 H 0.4820 0.8842 -0.0836 0.031(4) Uiso 1 1 d R . .
C5 C 0.30319(19) 0.76985(12) 0.04050(8) 0.0192(2) Uani 1 1 d . . .
H5 H 0.1436 0.8368 0.0313 0.033(4) Uiso 1 1 d R . .
C6 C 0.30784(18) 0.64896(12) 0.11579(7) 0.01643(19) Uani 1 1 d . . .
H6 H 0.1538 0.6311 0.1618 0.028(4) Uiso 1 1 d R . .
C7 C 0.70174(17) 0.14451(11) 0.28710(7) 0.01394(18) Uani 1 1 d . . .
C8 C 0.54323(18) 0.03029(12) 0.29358(8) 0.01772(19) Uani 1 1 d . . .
H8 H 0.3785 0.0348 0.3324 0.032(4) Uiso 1 1 d R . .
C9 C 0.6004(2) -0.09180(12) 0.25012(8) 0.0204(2) Uani 1 1 d . . .
H9 H 0.4761 -0.1804 0.2553 0.042(5) Uiso 1 1 d R . .
C10 C 0.8133(2) -0.09781(12) 0.20038(8) 0.0206(2) Uani 1 1 d . . .
H10 H 0.8430 -0.1930 0.1657 0.033(4) Uiso 1 1 d R . .
C11 C 0.9701(2) 0.01783(13) 0.19512(8) 0.0210(2) Uani 1 1 d . . .
H11 H 1.1382 0.0111 0.1590 0.031(4) Uiso 1 1 d R . .
C12 C 0.91637(18) 0.14066(12) 0.23902(8) 0.0182(2) Uani 1 1 d . . .
H12 H 1.0396 0.2292 0.2361 0.032(4) Uiso 1 1 d R . .
C13 C 0.21717(17) 0.35001(11) 0.46650(7) 0.01430(18) Uani 1 1 d . . .
C14 C -0.0605(2) 0.19669(14) 0.56110(9) 0.0260(2) Uani 1 1 d . . .
H14C H -0.0251 0.2405 0.6146 0.039 Uiso 1 1 calc R . .
H14B H 0.0314 0.1025 0.5616 0.039 Uiso 1 1 calc R . .
H14A H -0.2266 0.1750 0.5644 0.039 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 O1 1.4698(7) . ?
P1 O3 1.5773(7) . ?
P1 O2 1.5908(7) . ?
P1 N1 1.6318(9) . ?
O2 C1 1.4078(11) . ?
O3 C7 1.4011(12) . ?
O4 C13 1.2180(12) . ?
O5 C13 1.3442(12) . ?
O5 C14 1.4422(13) . ?
N1 N2 1.3965(11) . ?
N1 H1N 0.8463 . ?
N2 C13 1.3538(13) . ?
N2 H2N 0.8428 . ?
C1 C6 1.3861(14) . ?
C1 C2 1.3873(14) . ?
C2 C3 1.3929(14) . ?
C2 H2 1.0800 . ?
C3 C4 1.3913(15) . ?
C3 H3 1.0800 . ?
C4 C5 1.3928(15) . ?
C4 H4 1.0801 . ?
C5 C6 1.3964(14) . ?
C5 H5 1.0800 . ?
C6 H6 1.0800 . ?
C7 C8 1.3858(14) . ?
C7 C12 1.3883(14) . ?
C8 C9 1.3918(15) . ?
C8 H8 1.0801 . ?
C9 C10 1.3932(16) . ?
C9 H9 1.0800 . ?
C10 C11 1.3910(16) . ?
C10 H10 1.0801 . ?
C11 C12 1.3981(15) . ?
C11 H11 1.0800 . ?
C12 H12 1.0799 . ?
C14 H14C 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O3 117.96(4) . . ?
O1 P1 O2 114.25(4) . . ?
O3 P1 O2 99.62(4) . . ?
O1 P1 N1 111.54(4) . . ?
O3 P1 N1 104.97(4) . . ?
O2 P1 N1 107.27(4) . . ?
C1 O2 P1 119.84(6) . . ?
C7 O3 P1 124.14(6) . . ?
C13 O5 C14 115.50(9) . . ?
N2 N1 P1 118.62(7) . . ?
N2 N1 H1N 116.3 . . ?
P1 N1 H1N 120.8 . . ?
C13 N2 N1 120.37(8) . . ?
C13 N2 H2N 121.8 . . ?
N1 N2 H2N 117.6 . . ?
C6 C1 C2 122.30(9) . . ?
C6 C1 O2 118.53(9) . . ?
C2 C1 O2 119.07(9) . . ?
C1 C2 C3 118.51(9) . . ?
C1 C2 H2 122.3 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.50(10) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.84(10) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 120.47(10) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 117.5 . . ?
C1 C6 C5 118.36(9) . . ?
C1 C6 H6 123.8 . . ?
C5 C6 H6 117.8 . . ?
C8 C7 C12 122.09(10) . . ?
C8 C7 O3 116.48(9) . . ?
C12 C7 O3 121.36(9) . . ?
C7 C8 C9 118.99(10) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 120.21(10) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 121.1 . . ?
C11 C10 C9 119.81(10) . . ?
C11 C10 H10 123.9 . . ?
C9 C10 H10 116.3 . . ?
C10 C11 C12 120.74(10) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 118.15(10) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 120.7 . . ?
O4 C13 O5 125.04(9) . . ?
O4 C13 N2 126.37(9) . . ?
O5 C13 N2 108.59(8) . . ?
O5 C14 H14C 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14C C14 H14B 109.5 . . ?
O5 C14 H14A 109.5 . . ?
H14C C14 H14A 109.5 . . ?
H14B C14 H14A 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
O1 P1 O2 C1 -40.29(8) . . . . ?
O3 P1 O2 C1 -167.02(7) . . . . ?
N1 P1 O2 C1 83.89(8) . . . . ?
O1 P1 O3 C7 -77.87(9) . . . . ?
O2 P1 O3 C7 46.30(8) . . . . ?
N1 P1 O3 C7 157.22(8) . . . . ?
O1 P1 N1 N2 -175.47(7) . . . . ?
O3 P1 N1 N2 -46.61(8) . . . . ?
O2 P1 N1 N2 58.72(8) . . . . ?
P1 N1 N2 C13 93.05(10) . . . . ?
P1 O2 C1 C6 -102.17(9) . . . . ?
P1 O2 C1 C2 81.30(10) . . . . ?
C6 C1 C2 C3 -0.11(15) . . . . ?
O2 C1 C2 C3 176.28(9) . . . . ?
C1 C2 C3 C4 0.04(16) . . . . ?
C2 C3 C4 C5 0.09(16) . . . . ?
C3 C4 C5 C6 -0.15(17) . . . . ?
C2 C1 C6 C5 0.04(15) . . . . ?
O2 C1 C6 C5 -176.36(9) . . . . ?
C4 C5 C6 C1 0.09(16) . . . . ?
P1 O3 C7 C8 -126.75(9) . . . . ?
P1 O3 C7 C12 56.14(12) . . . . ?
C12 C7 C8 C9 -0.34(16) . . . . ?
O3 C7 C8 C9 -177.44(9) . . . . ?
C7 C8 C9 C10 -0.48(16) . . . . ?
C8 C9 C10 C11 0.74(17) . . . . ?
C9 C10 C11 C12 -0.18(17) . . . . ?
C8 C7 C12 C11 0.88(16) . . . . ?
O3 C7 C12 C11 177.84(9) . . . . ?
C10 C11 C12 C7 -0.61(16) . . . . ?
C14 O5 C13 O4 0.33(16) . . . . ?
C14 O5 C13 N2 -179.04(10) . . . . ?
N1 N2 C13 O4 1.34(16) . . . . ?
N1 N2 C13 O5 -179.30(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N(1) H(1N) O(4) 2_666 0.85 1.99 2.8378(12) 176 ?
N(2) H(2N) O(1) 1_455 0.84 1.98 2.8052(11) 168 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.062

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_m26
_database_code_depnum_ccdc_archive 'CCDC 989377'
_audit_update_record             
;
2014-03-01 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 N4 O5 P'
_chemical_formula_sum            'C10 H15 N4 O5 P'
_chemical_formula_weight         302.23

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                   12.2908(7)
_cell_length_b                   7.0588(4)
_cell_length_c                   17.6586(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.4250(10)
_cell_angle_gamma                90.00
_cell_volume                     1444.82(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1223
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SADABS v2008/1, (Sheldrick, 2008a)'

_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  "Bruker APEX DUO CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20710
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3491
_reflns_number_gt                3216
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL ver. 2009-9.1 (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXTL ver. 2009-9.1 (Sheldrick, 2008b)'
_computing_molecular_graphics    'SHELXTL ver. 2009-9.1 (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL ver. 2009-9.1 (Sheldrick, 2008b)'

_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)+(0.0200P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3491
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.09651(3) 0.85309(5) 0.19988(2) 0.01258(9) Uani 1 1 d . . .
O1 O -0.02508(9) 0.87220(15) 0.19822(6) 0.0162(2) Uani 1 1 d . . .
O2 O 0.24536(9) 0.38351(15) 0.19119(7) 0.0188(2) Uani 1 1 d . . .
O3 O 0.41798(9) 0.44935(16) 0.28674(7) 0.0216(2) Uani 1 1 d . . .
O4 O 0.36056(10) 0.94329(17) 0.38517(7) 0.0240(3) Uani 1 1 d . . .
O5 O 0.27154(10) 1.15254(18) 0.44332(7) 0.0259(3) Uani 1 1 d . . .
N1 N 0.15136(11) 0.67130(17) 0.25874(8) 0.0157(2) Uani 1 1 d . . .
H1N H 0.1083 0.5853 0.2699 0.019 Uiso 1 1 d R . .
N2 N 0.26801(11) 0.62602(18) 0.28124(8) 0.0166(3) Uani 1 1 d . . .
H2N H 0.3177 0.6876 0.3202 0.020 Uiso 1 1 d R . .
N3 N 0.18769(11) 1.02738(18) 0.23948(7) 0.0156(2) Uani 1 1 d . . .
H3N H 0.1980 1.1190 0.2096 0.019 Uiso 1 1 d R . .
N4 N 0.19153(11) 1.09519(18) 0.31493(8) 0.0176(3) Uani 1 1 d . . .
H4N H 0.1406 1.1781 0.3178 0.021 Uiso 1 1 d R . .
C1 C 0.30438(13) 0.4780(2) 0.24740(9) 0.0152(3) Uani 1 1 d . . .
C2 C 0.46755(14) 0.2888(2) 0.25914(11) 0.0256(4) Uani 1 1 d . . .
H2A H 0.5483 0.2736 0.2932 0.038 Uiso 1 1 calc R . .
H2B H 0.4637 0.3100 0.2035 0.038 Uiso 1 1 calc R . .
H2C H 0.4243 0.1740 0.2621 0.038 Uiso 1 1 calc R . .
C3 C 0.28226(13) 1.0537(2) 0.38101(9) 0.0187(3) Uani 1 1 d . . .
C4 C 0.35889(18) 1.1187(3) 0.52019(11) 0.0365(5) Uani 1 1 d . . .
H4A H 0.3387 1.1867 0.5621 0.055 Uiso 1 1 calc R . .
H4B H 0.4336 1.1639 0.5188 0.055 Uiso 1 1 calc R . .
H4C H 0.3636 0.9826 0.5318 0.055 Uiso 1 1 calc R . .
C5 C 0.10885(13) 0.8302(2) 0.10227(9) 0.0163(3) Uani 1 1 d . . .
C6 C 0.01358(15) 0.7581(2) 0.04122(9) 0.0208(3) Uani 1 1 d . . .
H6A H -0.0553 0.7284 0.0518 0.025 Uiso 1 1 calc R . .
C7 C 0.02002(17) 0.7299(2) -0.03523(10) 0.0279(4) Uani 1 1 d . . .
H7A H -0.0442 0.6790 -0.0766 0.033 Uiso 1 1 calc R . .
C8 C 0.11959(19) 0.7758(3) -0.05106(11) 0.0326(4) Uani 1 1 d . . .
H8A H 0.1235 0.7561 -0.1033 0.039 Uiso 1 1 calc R . .
C9 C 0.21382(18) 0.8504(3) 0.00876(11) 0.0332(4) Uani 1 1 d . . .
H9A H 0.2815 0.8838 -0.0028 0.040 Uiso 1 1 calc R . .
C10 C 0.20940(15) 0.8764(2) 0.08590(10) 0.0242(3) Uani 1 1 d . . .
H10A H 0.2744 0.9254 0.1272 0.029 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 O1 1.4911(11) . ?
P1 N1 1.6479(13) . ?
P1 N3 1.6544(13) . ?
P1 C5 1.7872(15) . ?
O2 C1 1.2154(18) . ?
O3 C1 1.3520(18) . ?
O3 C2 1.4460(19) . ?
O4 C3 1.2213(19) . ?
O5 C3 1.3458(19) . ?
O5 C4 1.443(2) . ?
N1 N2 1.3916(17) . ?
N1 H1N 0.8699 . ?
N2 C1 1.3515(19) . ?
N2 H2N 0.8701 . ?
N3 N4 1.4017(17) . ?
N3 H3N 0.8700 . ?
N4 C3 1.351(2) . ?
N4 H4N 0.8700 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.397(2) . ?
C5 C10 1.398(2) . ?
C6 C7 1.393(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 106.26(6) . . ?
O1 P1 N3 118.34(6) . . ?
N1 P1 N3 103.59(7) . . ?
O1 P1 C5 113.27(7) . . ?
N1 P1 C5 112.94(7) . . ?
N3 P1 C5 102.25(7) . . ?
C1 O3 C2 115.02(12) . . ?
C3 O5 C4 116.02(13) . . ?
N2 N1 P1 121.69(10) . . ?
N2 N1 H1N 114.9 . . ?
P1 N1 H1N 122.3 . . ?
C1 N2 N1 120.81(12) . . ?
C1 N2 H2N 119.2 . . ?
N1 N2 H2N 119.8 . . ?
N4 N3 P1 117.36(10) . . ?
N4 N3 H3N 110.9 . . ?
P1 N3 H3N 120.8 . . ?
C3 N4 N3 120.27(13) . . ?
C3 N4 H4N 119.9 . . ?
N3 N4 H4N 119.1 . . ?
O2 C1 N2 126.15(14) . . ?
O2 C1 O3 124.86(14) . . ?
N2 C1 O3 108.98(13) . . ?
O3 C2 H2A 109.5 . . ?
O3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O4 C3 O5 124.82(14) . . ?
O4 C3 N4 126.72(15) . . ?
O5 C3 N4 108.45(13) . . ?
O5 C4 H4A 109.5 . . ?
O5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.80(14) . . ?
C6 C5 P1 117.32(12) . . ?
C10 C5 P1 122.86(12) . . ?
C7 C6 C5 119.78(16) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 C6 120.17(17) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 120.45(16) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C8 C9 C10 120.06(17) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C5 119.72(17) . . ?
C9 C10 H10A 120.1 . . ?
C5 C10 H10A 120.1 . . ?

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
O1 P1 N1 N2 -172.58(11) . . . . ?
N3 P1 N1 N2 -47.19(13) . . . . ?
C5 P1 N1 N2 62.65(13) . . . . ?
P1 N1 N2 C1 -104.29(14) . . . . ?
O1 P1 N3 N4 48.92(13) . . . . ?
N1 P1 N3 N4 -68.31(12) . . . . ?
C5 P1 N3 N4 174.12(10) . . . . ?
P1 N3 N4 C3 106.71(14) . . . . ?
N1 N2 C1 O2 7.4(2) . . . . ?
N1 N2 C1 O3 -172.01(12) . . . . ?
C2 O3 C1 O2 -2.2(2) . . . . ?
C2 O3 C1 N2 177.27(13) . . . . ?
C4 O5 C3 O4 -1.6(2) . . . . ?
C4 O5 C3 N4 177.26(15) . . . . ?
N3 N4 C3 O4 -8.2(2) . . . . ?
N3 N4 C3 O5 172.97(13) . . . . ?
O1 P1 C5 C6 -24.82(14) . . . . ?
N1 P1 C5 C6 96.04(12) . . . . ?
N3 P1 C5 C6 -153.29(12) . . . . ?
O1 P1 C5 C10 156.82(13) . . . . ?
N1 P1 C5 C10 -82.32(14) . . . . ?
N3 P1 C5 C10 28.35(14) . . . . ?
C10 C5 C6 C7 1.0(2) . . . . ?
P1 C5 C6 C7 -177.39(12) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C5 -1.1(3) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
P1 C5 C10 C9 178.37(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.056

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 2_545 0.8700 2.0000 2.8686(17) 174.00 ?
N2 H2N O4 1_555 0.8700 2.1100 2.8791(18) 147.00 ?
N3 H3N O2 1_565 0.8700 2.0100 2.8198(17) 154.00 ?
N4 H4N O1 2_555 0.8700 1.9300 2.7833(18) 168.00 ?
