# 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 2018

####################################################################### 
# 
# 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_1-223K
_database_code_depnum_ccdc_archive 'CCDC 1858051'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C5 H14 P'
_chemical_formula_sum            'C11 H16 N3 O7 P'
_chemical_formula_weight         333.24

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/n'
_space_group_name_Hall           '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.325(5)
_cell_length_b                   19.765(9)
_cell_length_c                   6.921(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.830(8)
_cell_angle_gamma                90.00
_cell_volume                     1521.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2788
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(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  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11026
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3477
_reflns_number_gt                2788
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0824P)²+1.1307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3454
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1860
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
C1 C 0.3786(3) 0.54372(14) 0.2817(4) 0.0271(6) Uani 1 1 d . . .
C2 C 0.4975(3) 0.57339(14) 0.2945(4) 0.0263(6) Uani 1 1 d . . .
C3 C 0.5980(3) 0.53873(15) 0.2647(4) 0.0291(6) Uani 1 1 d . . .
H3 H 0.6710 0.5611 0.2726 0.035 Uiso 1 1 calc R . .
C4 C 0.5893(3) 0.47016(14) 0.2228(4) 0.0274(6) Uani 1 1 d . . .
C5 C 0.4799(3) 0.43690(14) 0.2049(4) 0.0283(6) Uani 1 1 d . . .
H5 H 0.4745 0.3911 0.1739 0.034 Uiso 1 1 calc R . .
C6 C 0.3800(3) 0.47154(14) 0.2329(4) 0.0281(6) Uani 1 1 d . . .
C7 C 0.3499(3) 0.20698(18) 0.0756(6) 0.0458(9) Uani 1 1 d . . .
H7A H 0.2768 0.1838 0.0853 0.069 Uiso 1 1 calc R . .
H7B H 0.3589 0.2085 -0.0595 0.069 Uiso 1 1 calc R . .
H7C H 0.3470 0.2522 0.1249 0.069 Uiso 1 1 calc R . .
C8 C 0.4538(3) 0.15679(19) 0.4657(5) 0.0442(8) Uani 1 1 d . . .
H8A H 0.4504 0.2013 0.5197 0.066 Uiso 1 1 calc R . .
H8B H 0.5198 0.1323 0.5416 0.066 Uiso 1 1 calc R . .
H8C H 0.3801 0.1333 0.4694 0.066 Uiso 1 1 calc R . .
C9 C 0.4858(3) 0.08087(16) 0.1186(6) 0.0460(9) Uani 1 1 d . . .
H9A H 0.4179 0.0542 0.1372 0.069 Uiso 1 1 calc R . .
H9B H 0.5585 0.0597 0.1846 0.069 Uiso 1 1 calc R . .
H9C H 0.4870 0.0843 -0.0194 0.069 Uiso 1 1 calc R . .
C10 C 0.6106(3) 0.20947(16) 0.2104(5) 0.0340(7) Uani 1 1 d . . .
H10A H 0.6035 0.2544 0.2637 0.041 Uiso 1 1 calc R . .
H10B H 0.6771 0.1869 0.2943 0.041 Uiso 1 1 calc R . .
C11 C 0.6395(3) 0.21634(18) 0.0018(5) 0.0434(8) Uani 1 1 d . . .
H11A H 0.6542 0.1723 -0.0475 0.065 Uiso 1 1 calc R . .
H11B H 0.7097 0.2440 0.0072 0.065 Uiso 1 1 calc R . .
H11C H 0.5727 0.2369 -0.0839 0.065 Uiso 1 1 calc R . .
N1 N 0.5139(2) 0.64476(13) 0.3392(4) 0.0344(6) Uani 1 1 d . . .
N2 N 0.6944(2) 0.43303(14) 0.1967(4) 0.0357(6) Uani 1 1 d . . .
N3 N 0.2690(2) 0.43331(13) 0.2123(4) 0.0377(6) Uani 1 1 d . . .
O1 O 0.28698(19) 0.57584(11) 0.2975(4) 0.0385(5) Uani 1 1 d . . .
O2 O 0.4538(3) 0.67110(12) 0.4482(4) 0.0539(7) Uani 1 1 d . . .
O3 O 0.5879(3) 0.67622(12) 0.2636(5) 0.0626(8) Uani 1 1 d . . .
O4 O 0.7895(2) 0.46455(14) 0.2043(4) 0.0518(7) Uani 1 1 d . . .
O5 O 0.6855(2) 0.37207(11) 0.1645(4) 0.0491(7) Uani 1 1 d . . .
O6 O 0.2578(3) 0.38320(15) 0.1039(5) 0.0690(9) Uani 1 1 d . . .
O7 O 0.1928(2) 0.44982(13) 0.3059(5) 0.0611(8) Uani 1 1 d . . .
P1 P 0.47458(6) 0.16317(4) 0.21739(12) 0.0279(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.238(3) . ?
C1 C2 1.456(4) . ?
C1 C6 1.467(4) . ?
C2 C3 1.377(4) . ?
C2 N1 1.448(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 N2 1.438(4) . ?
C5 C6 1.366(4) . ?
C5 H5 0.9300 . ?
C6 N3 1.451(4) . ?
C7 P1 1.785(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 P1 1.782(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 P1 1.778(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.545(5) . ?
C10 P1 1.800(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 O2 1.223(4) . ?
N1 O3 1.236(4) . ?
N2 O5 1.226(4) . ?
N2 O4 1.237(4) . ?
N3 O7 1.217(4) . ?
N3 O6 1.235(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 124.7(3) . . ?
O1 C1 C6 124.4(3) . . ?
C2 C1 C6 110.8(2) . . ?
C3 C2 N1 116.1(3) . . ?
C3 C2 C1 124.9(3) . . ?
N1 C2 C1 119.0(2) . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 N2 119.8(3) . . ?
C5 C4 N2 119.6(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 N3 116.8(3) . . ?
C5 C6 C1 124.4(3) . . ?
N3 C6 C1 118.8(3) . . ?
P1 C7 H7A 109.5 . . ?
P1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
P1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
P1 C8 H8A 109.5 . . ?
P1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
P1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
P1 C9 H9A 109.5 . . ?
P1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
P1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 P1 113.7(2) . . ?
C11 C10 H10A 108.8 . . ?
P1 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
P1 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 N1 O3 123.2(3) . . ?
O2 N1 C2 118.8(3) . . ?
O3 N1 C2 118.0(3) . . ?
O5 N2 O4 122.9(3) . . ?
O5 N2 C4 118.9(3) . . ?
O4 N2 C4 118.2(3) . . ?
O7 N3 O6 122.5(3) . . ?
O7 N3 C6 119.7(3) . . ?
O6 N3 C6 117.7(3) . . ?
C9 P1 C8 109.74(18) . . ?
C9 P1 C7 109.80(18) . . ?
C8 P1 C7 109.29(18) . . ?
C9 P1 C10 109.36(16) . . ?
C8 P1 C10 109.30(16) . . ?
C7 P1 C10 109.33(16) . . ?

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 C1 C2 C3 -175.7(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
O1 C1 C2 N1 3.5(4) . . . . ?
C6 C1 C2 N1 179.3(2) . . . . ?
N1 C2 C3 C4 179.5(3) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C2 C3 C4 N2 -178.3(3) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
N2 C4 C5 C6 178.9(3) . . . . ?
C4 C5 C6 N3 -179.8(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
O1 C1 C6 C5 176.3(3) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
O1 C1 C6 N3 -3.8(4) . . . . ?
C2 C1 C6 N3 -179.6(2) . . . . ?
C3 C2 N1 O2 -147.5(3) . . . . ?
C1 C2 N1 O2 33.3(4) . . . . ?
C3 C2 N1 O3 32.9(4) . . . . ?
C1 C2 N1 O3 -146.3(3) . . . . ?
C3 C4 N2 O5 178.2(3) . . . . ?
C5 C4 N2 O5 -2.0(4) . . . . ?
C3 C4 N2 O4 -3.1(4) . . . . ?
C5 C4 N2 O4 176.7(3) . . . . ?
C5 C6 N3 O7 150.5(3) . . . . ?
C1 C6 N3 O7 -29.5(4) . . . . ?
C5 C6 N3 O6 -26.9(4) . . . . ?
C1 C6 N3 O6 153.1(3) . . . . ?
C11 C10 P1 C9 58.2(3) . . . . ?
C11 C10 P1 C8 178.3(2) . . . . ?
C11 C10 P1 C7 -62.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11C O3 0.96 2.64 3.569(5) 164.0 3_665
C10 H10B O6 0.97 2.57 3.442(4) 149.5 4_666
C10 H10A O5 0.97 2.64 3.354(4) 130.4 .
C10 H10A O2 0.97 2.66 3.512(4) 147.4 3_666
C9 H9B O4 0.96 2.57 3.477(5) 158.3 2_645
C9 H9A O7 0.96 2.48 3.387(4) 156.6 2_545
C9 H9A O1 0.96 2.48 3.250(4) 136.8 2_545
C8 H8C O1 0.96 2.64 3.383(4) 134.6 2_545
C7 H7A O2 0.96 2.59 3.485(5) 155.3 2_545
C7 H7A O1 0.96 2.44 3.226(4) 139.0 2_545
C7 H7A O1 0.96 2.44 3.226(4) 139.0 2_545
C7 H7A O2 0.96 2.59 3.485(5) 155.3 2_545
C8 H8C O1 0.96 2.64 3.383(4) 134.6 2_545
C9 H9A O1 0.96 2.48 3.250(4) 136.8 2_545
C9 H9A O7 0.96 2.48 3.387(4) 156.6 2_545
C9 H9B O4 0.96 2.57 3.477(5) 158.3 2_645
C10 H10A O2 0.97 2.66 3.512(4) 147.4 3_666
C10 H10A O5 0.97 2.64 3.354(4) 130.4 .
C10 H10B O6 0.97 2.57 3.442(4) 149.5 4_666
C11 H11C O3 0.96 2.64 3.569(5) 164.0 3_665

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_1-333K
_database_code_depnum_ccdc_archive 'CCDC 1858056'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C5 H14 P'
_chemical_formula_sum            'C11 H16 N3 O7 P'
_chemical_formula_weight         333.24

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.412(2)
_cell_length_b                   19.766(4)
_cell_length_c                   7.048(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.10(4)
_cell_angle_gamma                90.00
_cell_volume                     1462.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    333(2)
_cell_measurement_reflns_used    700
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      333(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  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2380
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1300
_reflns_number_gt                700
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0010P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1146
_refine_ls_number_parameters     121
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.1055
_refine_ls_wR_factor_ref         0.3165
_refine_ls_wR_factor_gt          0.2832
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0000 -0.1401(5) -1.2500 0.534(13) Uani 1 2 d SU . .
O4 O -0.0832(6) 0.1781(3) -1.2508(14) 0.363(6) Uani 1 1 d U . .
O2 O -0.2123(5) -0.1285(2) -1.2442(14) 0.414(6) Uani 1 1 d DU . .
O3 O -0.2998(5) -0.0440(3) -1.2452(16) 0.451(6) Uani 1 1 d DU . .
N1 N -0.2099(7) -0.0700(3) -1.2601(14) 0.272(4) Uani 1 1 d DU . .
N2 N 0.0000 0.1437(4) -1.2500 0.262(6) Uani 1 2 d SDU . .
C1 C 0.0000 -0.06693(14) -1.2500 0.214(4) Uani 1 2 d SDU . .
C2 C -0.1059(3) -0.02999(13) -1.2498(9) 0.203(3) Uani 1 1 d DU . .
C3 C -0.1067(3) 0.04239(14) -1.2500(9) 0.229(4) Uani 1 1 d DU . .
H3A H -0.1755 0.0659 -1.2430 0.274 Uiso 1 1 d R . .
C4 C 0.0000 0.07912(15) -1.2500 0.230(5) Uani 1 2 d SDU . .
P1 P -0.5000 0.1661(2) -1.2500 0.2245(18) Uani 1 2 d SDU . .
C9 C -0.4266(3) 0.1737(8) -1.5539(6) 0.357(8) Uani 0.50 1 d PDU . .
H9A H -0.3981 0.1847 -1.6614 0.535 Uiso 0.50 1 d PR . .
H9B H -0.3637 0.1463 -1.4518 0.535 Uiso 0.50 1 d PR . .
H9C H -0.5054 0.1492 -1.6113 0.535 Uiso 0.50 1 d PR . .
C6 C -0.5000 0.0815(6) -1.2500 0.415(8) Uani 1 2 d SDU . .
H6A H -0.4274 0.0653 -1.2733 0.622 Uiso 0.50 1 d PR . .
H6B H -0.4960 0.0653 -1.1192 0.622 Uiso 0.50 1 d PR . .
H6C H -0.5766 0.0653 -1.3576 0.622 Uiso 0.50 1 d PR . .
C8 C -0.5331(5) 0.1913(9) -1.4878(14) 0.299(4) Uani 0.50 1 d PDU . .
H8A H -0.4550 0.2164 -1.4293 0.359 Uiso 0.50 1 d PR . .
H8B H -0.5961 0.2193 -1.5881 0.359 Uiso 0.50 1 d PR . .
C5 C -0.6251(12) 0.2077(9) -1.168(2) 0.252(5) Uani 0.50 1 d PDU . 1
H5A H -0.6143 0.2558 -1.1714 0.378 Uiso 0.50 1 d PR . 1
H5B H -0.7050 0.1949 -1.2745 0.378 Uiso 0.50 1 d PR . 1
H5C H -0.6243 0.1949 -1.0361 0.378 Uiso 0.50 1 d PR . 1
C7 C -0.6142(14) 0.2228(8) -1.329(2) 0.217(4) Uani 0.50 1 d PDU . 2
H7A H -0.6319 0.2256 -1.4734 0.325 Uiso 0.50 1 d PR . 2
H7B H -0.6822 0.1991 -1.3095 0.325 Uiso 0.50 1 d PR . 2
H7C H -0.6070 0.2676 -1.2726 0.325 Uiso 0.50 1 d PR . 2


_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
O1 C1 1.447(10) . ?
O4 N2 1.166(8) . ?
O2 N1 1.164(8) . ?
O3 N1 1.188(11) . ?
N1 C2 1.405(8) . ?
N2 O4 1.166(8) 2_552 ?
N2 C4 1.277(9) . ?
C1 C2 1.412(4) . ?
C1 C2 1.412(4) 2_552 ?
C2 C3 1.431(3) . ?
C3 C4 1.418(4) . ?
C3 H3A 0.9300 . ?
C4 C3 1.418(4) 2_552 ?
P1 C7 1.641(15) 2_452 ?
P1 C7 1.641(15) . ?
P1 C8 1.644(11) 2_452 ?
P1 C8 1.644(11) . ?
P1 C6 1.673(13) . ?
P1 C5 1.923(16) . ?
P1 C5 1.923(16) 2_452 ?
C9 C8 1.503(5) . ?
C9 C5 1.588(17) 2_452 ?
C9 H9A 0.9599 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C5 1.737(14) 2_452 ?
C8 C7 1.82(2) . ?
C8 H8A 0.9599 . ?
C8 H8B 0.9599 . ?
C5 C9 1.588(16) 2_452 ?
C5 C8 1.737(14) 2_452 ?
C5 H5A 0.9601 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C5 H7B 0.9688 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9599 . ?
C7 H7C 0.9599 . ?

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 N1 O3 111.6(9) . . ?
O2 N1 C2 127.3(7) . . ?
O3 N1 C2 119.5(6) . . ?
O4 N2 O4 108.7(10) 2_552 . ?
O4 N2 C4 125.6(5) 2_552 . ?
O4 N2 C4 125.6(5) . . ?
C2 C1 C2 117.7(3) . 2_552 ?
C2 C1 O1 121.14(16) . . ?
C2 C1 O1 121.14(16) 2_552 . ?
N1 C2 C1 114.5(4) . . ?
N1 C2 C3 123.9(4) . . ?
C1 C2 C3 121.5(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 120.4 . . ?
N2 C4 C3 120.79(17) . 2_552 ?
N2 C4 C3 120.79(16) . . ?
C3 C4 C3 118.4(3) 2_552 . ?
C7 P1 C7 93.9(11) 2_452 . ?
C7 P1 C8 67.3(7) 2_452 2_452 ?
C7 P1 C8 88.4(8) . 2_452 ?
C7 P1 C8 88.4(8) 2_452 . ?
C7 P1 C8 67.3(7) . . ?
C8 P1 C8 144.7(11) 2_452 . ?
C7 P1 C6 133.0(6) 2_452 . ?
C7 P1 C6 133.0(6) . . ?
C8 P1 C6 107.7(6) 2_452 . ?
C8 P1 C6 107.7(6) . . ?
C7 P1 C5 101.0(8) 2_452 . ?
C7 P1 C5 39.2(8) . . ?
C8 P1 C5 57.6(5) 2_452 . ?
C8 P1 C5 106.0(5) . . ?
C6 P1 C5 115.3(5) . . ?
C7 P1 C5 39.2(8) 2_452 2_452 ?
C7 P1 C5 101.0(8) . 2_452 ?
C8 P1 C5 106.0(6) 2_452 2_452 ?
C8 P1 C5 57.6(5) . 2_452 ?
C6 P1 C5 115.3(5) . 2_452 ?
C5 P1 C5 129.3(10) . 2_452 ?
C7 P1 H8A 57.5 2_452 . ?
C7 P1 H8A 78.3 . . ?
C8 P1 H8A 121.6 2_452 . ?
C8 P1 H8A 31.5 . . ?
C6 P1 H8A 122.9 . . ?
C5 P1 H8A 114.6 . . ?
C5 P1 H8A 28.2 2_452 . ?
C8 C9 C5 68.3(6) . 2_452 ?
C8 C9 H9A 139.3 . . ?
C5 C9 H9A 124.8 2_452 . ?
C8 C9 H9B 110.9 . . ?
C5 C9 H9B 67.7 2_452 . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 60.7 . . ?
C5 C9 H9C 123.7 2_452 . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H8A 38.9 . . ?
C5 C9 H8A 35.3 2_452 . ?
H9A C9 H8A 128.0 . . ?
H9B C9 H8A 99.5 . . ?
H9C C9 H8A 99.6 . . ?
P1 C6 H6A 109.5 . . ?
P1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
P1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C9 C8 P1 110.8(6) . . ?
C9 C8 C5 58.1(6) . 2_452 ?
P1 C8 C5 69.3(6) . 2_452 ?
C11 C8 C7 159.7(8) . . ?
P1 C8 C7 56.3(5) . . ?
C5 C8 C7 101.6(9) 2_452 . ?
C9 C8 H9C 39.0 . . ?
P1 C8 H9C 117.3 . . ?
C5 C8 H9C 94.3 2_452 . ?
C7 C8 H9C 157.8 . . ?
C9 C8 H8A 61.7 . . ?
P1 C8 H8A 85.2 . . ?
C5 C8 H8A 21.9 2_452 . ?
C7 C8 H8A 99.8 . . ?
H9C C8 H8A 100.7 . . ?
C9 C8 H8B 111.6 . . ?
P1 C8 H8B 137.0 . . ?
C5 C8 H8B 130.6 2_452 . ?
C7 C8 H8B 81.0 . . ?
H9C C8 H8B 100.3 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 H7A 159.8 . . ?
P1 C8 H7A 86.6 . . ?
C5 C8 H7A 123.4 2_452 . ?
C7 C8 H7A 31.0 . . ?
H9C C8 H7A 141.4 . . ?
H8A C8 H7A 111.7 . . ?
H8B C8 H7A 50.4 . . ?
C9 C5 C8 53.5(5) 2_452 2_452 ?
C9 C5 P1 94.7(8) 2_452 . ?
C8 C5 P1 53.1(6) 2_452 . ?
C9 C5 H5A 116.3 2_452 . ?
C8 C5 H5A 95.1 2_452 . ?
P1 C5 H5A 107.3 . . ?
C9 C5 H5B 122.1 2_452 . ?
C8 C5 H5B 151.4 2_452 . ?
P1 C5 H5B 103.9 . . ?
H5A C5 H5B 109.5 . . ?
C9 C5 H5C 22.5 2_452 . ?
C8 C5 H5C 74.1 2_452 . ?
P1 C5 H5C 116.9 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 C5 H7B 141.3 2_452 . ?
C8 C5 H7B 136.9 2_452 . ?
P1 C5 H7B 83.9 . . ?
H5A C5 H7B 100.9 . . ?
H5B C5 H7B 25.8 . . ?
H5C C5 H7B 134.3 . . ?
C9 C5 H7C 140.7 2_452 . ?
C8 C5 H7C 98.8 2_452 . ?
P1 C5 H7C 85.7 . . ?
H5A C5 H7C 30.1 . . ?
H5B C5 H7C 95.6 . . ?
H5C C5 H7C 139.3 . . ?
H7B C5 H7C 78.0 . . ?
P1 C7 C8 56.4(7) . . ?
P1 C7 H5A 108.9 . . ?
C8 C7 H5A 151.2 . . ?
P1 C7 H5B 102.8 . . ?
C8 C7 H5B 131.7 . . ?
H5A C7 H5B 72.8 . . ?
P1 C7 H7A 101.9 . . ?
C8 C7 H7A 46.5 . . ?
H5A C7 H7A 144.6 . . ?
H5B C7 H7A 117.3 . . ?
P1 C7 H7B 101.5 . . ?
C8 C7 H7B 123.7 . . ?
H5A C7 H7B 81.4 . . ?
H5B C7 H7B 8.8 . . ?
H7A C7 H7B 109.5 . . ?
P1 C7 H7C 124.2 . . ?
C8 C7 H7C 126.0 . . ?
H5A C7 H7C 37.4 . . ?
H5B C7 H7C 102.1 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O2 N1 C2 C1 9.8(14) . . . . ?
O3 N1 C2 C1 174.4(8) . . . . ?
O2 N1 C2 C3 -173.4(10) . . . . ?
O3 N1 C2 C3 -8.8(13) . . . . ?
C2 C1 C2 N1 177.0(7) 2_552 . . . ?
O1 C1 C2 N1 -3.0(7) . . . . ?
C2 C1 C2 C3 0.0(4) 2_552 . . . ?
O1 C1 C2 C3 -180.0(4) . . . . ?
N1 C2 C3 C4 -176.7(6) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
O4 N2 C4 C3 -0.3(6) 2_552 . . 2_552 ?
O4 N2 C4 C3 179.7(6) . . . 2_552 ?
O4 N2 C4 C3 179.7(6) 2_552 . . . ?
O4 N2 C4 C3 -0.3(6) . . . . ?
C2 C3 C4 N2 -180.0(4) . . . . ?
C2 C3 C4 C3 0.0(4) . . . 2_552 ?
C5 C9 C8 P1 -47.0(10) 2_452 . . . ?
C5 C9 C8 C7 0(4) 2_452 . . . ?
C7 P1 C8 C9 67.5(11) 2_452 . . . ?
C7 P1 C8 C9 162.4(13) . . . . ?
C8 P1 C8 C9 112.4(10) 2_452 . . . ?
C6 P1 C8 C9 -67.6(10) . . . . ?
C5 P1 C8 C9 168.5(10) . . . . ?
C5 P1 C8 C9 41.7(10) 2_452 . . . ?
C7 P1 C8 C5 25.8(9) 2_452 . . 2_452 ?
C7 P1 C8 C5 120.7(10) . . . 2_452 ?
C8 P1 C8 C5 70.8(7) 2_452 . . 2_452 ?
C6 P1 C8 C5 -109.2(7) . . . 2_452 ?
C5 P1 C8 C5 126.8(11) . . . 2_452 ?
C7 P1 C8 C7 -94.9(12) 2_452 . . . ?
C8 P1 C8 C7 -50.0(6) 2_452 . . . ?
C6 P1 C8 C7 130.0(6) . . . . ?
C5 P1 C8 C7 6.1(9) . . . . ?
C5 P1 C8 C7 -120.7(10) 2_452 . . . ?
C7 P1 C5 C9 -90.1(9) 2_452 . . 2_452 ?
C7 P1 C5 C9 -172.7(16) . . . 2_452 ?
C8 P1 C5 C9 -36.2(8) 2_452 . . 2_452 ?
C8 P1 C5 C9 178.4(9) . . . 2_452 ?
C6 P1 C5 C9 59.4(9) . . . 2_452 ?
C5 P1 C5 C9 -120.6(8) 2_452 . . 2_452 ?
C7 P1 C5 C8 -53.9(9) 2_452 . . 2_452 ?
C7 P1 C5 C8 -136.5(14) . . . 2_452 ?
C8 P1 C5 C8 -145.4(12) . . . 2_452 ?
C6 P1 C5 C8 95.6(7) . . . 2_452 ?
C5 P1 C5 C8 -84.4(7) 2_452 . . 2_452 ?
C7 P1 C7 C8 86.6(8) 2_452 . . . ?
C8 P1 C7 C8 153.7(9) 2_452 . . . ?
C6 P1 C7 C8 -93.4(8) . . . . ?
C5 P1 C7 C8 -170.7(13) . . . . ?
C5 P1 C7 C8 47.7(8) 2_452 . . . ?
C9 C8 C7 P1 -55(4) . . . . ?
C5 C8 C7 P1 -55.2(8) 2_452 . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.069

# start Validation Reply Form

_vrf_PLAT242_1-333K              
;
PROBLEM: Low ??MainMol?? Ueq as Compared to Neighbors of      C1 Check
RESPONSE: In picrate anion, the O atoms connected to it have relatively 
          large atomic displacement parameters.
;

# end Validation Reply Form
####################################################################### 
# 
# 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_2-298K
_database_code_depnum_ccdc_archive 'CCDC 1858057'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7, C4 H12 O P'
_chemical_formula_sum            'C10 H14 N3 O8 P'
_chemical_formula_weight         335.21

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'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4008(15)
_cell_length_b                   10.413(2)
_cell_length_c                   10.972(2)
_cell_angle_alpha                109.76(3)
_cell_angle_beta                 99.84(3)
_cell_angle_gamma                104.20(3)
_cell_volume                     741.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1797
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9515
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4251
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2608
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1416P)²+0.4027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2579
_refine_ls_number_parameters     203
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2502
_refine_ls_wR_factor_gt          0.2314
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.158
_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
C1 C 0.7318(7) 0.0045(5) 1.0603(4) 0.0426(11) Uani 1 1 d . . .
C2 C 0.8307(7) 0.1595(6) 1.1163(5) 0.0466(12) Uani 1 1 d . . .
C3 C 0.9034(7) 0.2336(6) 1.0449(5) 0.0504(12) Uani 1 1 d . . .
H3 H 0.9571 0.3337 1.0851 0.060 Uiso 1 1 calc R . .
C4 C 0.8971(7) 0.1597(6) 0.9122(5) 0.0504(12) Uani 1 1 d . . .
C5 C 0.8152(7) 0.0129(6) 0.8515(5) 0.0468(12) Uani 1 1 d . . .
H5 H 0.8138 -0.0359 0.7628 0.056 Uiso 1 1 calc R . .
C6 C 0.7349(7) -0.0627(5) 0.9208(4) 0.0426(11) Uani 1 1 d . . .
C7 C 0.2829(9) 0.3695(7) 0.5918(7) 0.0753(17) Uani 1 1 d . . .
H7A H 0.1686 0.3480 0.6214 0.113 Uiso 1 1 calc R . .
H7B H 0.2484 0.3283 0.4951 0.113 Uiso 1 1 calc R . .
H7C H 0.3416 0.4723 0.6245 0.113 Uiso 1 1 calc R . .
C8 C 0.6619(9) 0.3354(8) 0.6002(7) 0.0773(18) Uani 1 1 d . . .
H8A H 0.6270 0.2925 0.5034 0.116 Uiso 1 1 calc R . .
H8B H 0.7537 0.2971 0.6359 0.116 Uiso 1 1 calc R . .
H8C H 0.7189 0.4381 0.6312 0.116 Uiso 1 1 calc R . .
C9 C 0.5140(10) 0.3657(6) 0.8358(5) 0.0698(17) Uani 1 1 d . . .
H9A H 0.5763 0.4683 0.8716 0.105 Uiso 1 1 calc R . .
H9B H 0.6009 0.3219 0.8679 0.105 Uiso 1 1 calc R . .
H9C H 0.3988 0.3448 0.8647 0.105 Uiso 1 1 calc R . .
C10 C 0.3465(8) 0.1011(6) 0.5943(5) 0.0573(14) Uani 1 1 d . . .
H10A H 0.2228 0.0764 0.6141 0.069 Uiso 1 1 calc R . .
H10B H 0.3234 0.0587 0.4972 0.069 Uiso 1 1 calc R . .
N1 N 0.8529(9) 0.2421(6) 1.2574(5) 0.0849(17) Uani 1 1 d U . .
N2 N 0.9780(7) 0.2375(6) 0.8378(5) 0.0642(13) Uani 1 1 d . . .
N3 N 0.6508(7) -0.2183(5) 0.8486(4) 0.0582(12) Uani 1 1 d . . .
O1 O 0.6576(6) -0.0618(4) 1.1235(4) 0.0696(12) Uani 1 1 d . . .
O2 O 0.8534(14) 0.1798(7) 1.3330(6) 0.178(3) Uani 1 1 d U . .
O3 O 0.9125(11) 0.3688(6) 1.3058(6) 0.135(2) Uani 1 1 d . . .
O4 O 1.0482(8) 0.3699(5) 0.8933(5) 0.0981(17) Uani 1 1 d . . .
O5 O 0.9763(6) 0.1682(5) 0.7213(4) 0.0774(13) Uani 1 1 d . . .
O6 O 0.6553(9) -0.2740(5) 0.7340(5) 0.121(2) Uani 1 1 d . . .
O7 O 0.5869(11) -0.2910(5) 0.9029(5) 0.138(3) Uani 1 1 d . . .
O8 O 0.4716(6) 0.0444(4) 0.6548(4) 0.0673(11) Uani 1 1 d . . .
H8 H 0.4371 0.0318 0.7182 0.101 Uiso 1 1 calc R . .
P1 P 0.4503(2) 0.29530(14) 0.65586(12) 0.0493(5) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.235(6) . ?
C1 C2 1.454(7) . ?
C1 C6 1.459(6) . ?
C2 C3 1.360(7) . ?
C2 N1 1.452(6) . ?
C3 C4 1.384(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(7) . ?
C4 N2 1.435(7) . ?
C5 C6 1.371(7) . ?
C5 H5 0.9300 . ?
C6 N3 1.453(6) . ?
C7 P1 1.779(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 P1 1.783(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 P1 1.786(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O8 1.404(7) . ?
C10 P1 1.809(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 O3 1.174(7) . ?
N1 O2 1.215(9) . ?
N2 O4 1.230(7) . ?
N2 O5 1.233(6) . ?
N3 O7 1.173(6) . ?
N3 O6 1.204(6) . ?
O8 H8 0.8200 . ?

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 C1 C2 124.3(4) . . ?
O1 C1 C6 124.5(5) . . ?
C2 C1 C6 111.1(4) . . ?
C3 C2 N1 117.2(5) . . ?
C3 C2 C1 124.4(4) . . ?
N1 C2 C1 118.5(5) . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 N2 119.6(5) . . ?
C3 C4 N2 119.8(5) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 N3 116.7(4) . . ?
C5 C6 C1 123.7(4) . . ?
N3 C6 C1 119.6(4) . . ?
P1 C7 H7A 109.5 . . ?
P1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
P1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
P1 C8 H8A 109.5 . . ?
P1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
P1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
P1 C9 H9A 109.5 . . ?
P1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
P1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O8 C10 P1 110.6(4) . . ?
O8 C10 H10A 109.5 . . ?
P1 C10 H10A 109.5 . . ?
O8 C10 H10B 109.5 . . ?
P1 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O3 N1 O2 117.6(6) . . ?
O3 N1 C2 122.2(6) . . ?
O2 N1 C2 117.9(6) . . ?
O4 N2 O5 123.0(5) . . ?
O4 N2 C4 118.7(5) . . ?
O5 N2 C4 118.3(5) . . ?
O7 N3 O6 119.6(5) . . ?
O7 N3 C6 120.7(5) . . ?
O6 N3 C6 119.6(5) . . ?
C10 O8 H8 109.5 . . ?
C7 P1 C8 109.2(3) . . ?
C7 P1 C9 111.0(3) . . ?
C8 P1 C9 110.2(3) . . ?
C7 P1 C10 110.8(3) . . ?
C8 P1 C10 108.1(3) . . ?
C9 P1 C10 107.6(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
O1 C1 C2 C3 -176.3(5) . . . . ?
C6 C1 C2 C3 4.8(7) . . . . ?
O1 C1 C2 N1 3.1(8) . . . . ?
C6 C1 C2 N1 -175.8(4) . . . . ?
N1 C2 C3 C4 176.1(5) . . . . ?
C1 C2 C3 C4 -4.5(8) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C2 C3 C4 N2 -178.5(4) . . . . ?
C3 C4 C5 C6 1.2(7) . . . . ?
N2 C4 C5 C6 -179.1(4) . . . . ?
C4 C5 C6 N3 180.0(4) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
O1 C1 C6 C5 178.9(5) . . . . ?
C2 C1 C6 C5 -2.2(6) . . . . ?
O1 C1 C6 N3 -1.6(7) . . . . ?
C2 C1 C6 N3 177.3(4) . . . . ?
C3 C2 N1 O3 7.7(10) . . . . ?
C1 C2 N1 O3 -171.8(7) . . . . ?
C3 C2 N1 O2 -154.9(7) . . . . ?
C1 C2 N1 O2 25.6(9) . . . . ?
C5 C4 N2 O4 178.8(5) . . . . ?
C3 C4 N2 O4 -1.5(8) . . . . ?
C5 C4 N2 O5 -2.2(7) . . . . ?
C3 C4 N2 O5 177.5(5) . . . . ?
C5 C6 N3 O7 176.7(6) . . . . ?
C1 C6 N3 O7 -2.8(8) . . . . ?
C5 C6 N3 O6 0.3(8) . . . . ?
C1 C6 N3 O6 -179.2(5) . . . . ?
O8 C10 P1 C7 -174.5(3) . . . . ?
O8 C10 P1 C8 66.0(4) . . . . ?
O8 C10 P1 C9 -53.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 O2 0.82 2.49 2.969(8) 118.1 2_657
O8 H8 O1 0.82 1.94 2.728(5) 161.2 2_657
C10 H10B O8 0.97 2.59 3.322(6) 132.7 2_656
C10 H10A O5 0.97 2.54 3.395(7) 146.8 1_455
C9 H9A O7 0.96 2.39 3.278(8) 153.6 1_565
C8 H8B O5 0.96 2.61 3.565(8) 174.3 .
C7 H7B O6 0.96 2.64 3.515(8) 150.9 2_656
C7 H7B O6 0.96 2.64 3.515(8) 150.9 2_656
C8 H8B O5 0.96 2.61 3.565(8) 174.3 .
C9 H9A O7 0.96 2.39 3.278(8) 153.6 1_565
C10 H10A O5 0.97 2.54 3.395(7) 146.8 1_455
C10 H10B O8 0.97 2.59 3.322(6) 132.7 2_656
O8 H8 O1 0.82 1.94 2.728(5) 161.2 2_657
O8 H8 O2 0.82 2.49 2.969(8) 118.1 2_657
C7 H7B O6 0.96 2.64 3.515(8) 150.9 2_656
C8 H8B O5 0.96 2.61 3.565(8) 174.3 .
C9 H9A O7 0.96 2.39 3.278(8) 153.6 1_565
C10 H10A O5 0.97 2.54 3.395(7) 146.8 1_455
C10 H10B O8 0.97 2.59 3.322(6) 132.7 2_656
O8 H8 O1 0.82 1.94 2.728(5) 161.2 2_657
O8 H8 O2 0.82 2.49 2.969(8) 118.1 2_657

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.314
_refine_diff_density_min         -0.870
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_3-298K
_database_code_depnum_ccdc_archive 'CCDC 1858060'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O7,C8 H18 P'
_chemical_formula_sum            'C14 H20 N3 O7 P'
_chemical_formula_weight         373.30

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/n'
_space_group_name_Hall           '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.300(3)
_cell_length_b                   19.943(4)
_cell_length_c                   7.3103(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.55(3)
_cell_angle_gamma                90.00
_cell_volume                     1773.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2239
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.00

_exptl_crystal_description       strip
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9960
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3125
_reflns_number_gt                2239
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1392P)²+0.8942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3117
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2455
_refine_ls_wR_factor_gt          0.2229
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 1.0989(3) 0.0321(2) 0.7643(6) 0.0705(11) Uani 1 1 d . . .
C2 C 1.0000(3) 0.07044(19) 0.6997(6) 0.0658(10) Uani 1 1 d . . .
C3 C 0.8960(3) 0.04578(19) 0.6879(5) 0.0646(10) Uani 1 1 d . . .
H3 H 0.8360 0.0733 0.6492 0.078 Uiso 1 1 calc R . .
C4 C 0.8801(3) -0.02006(18) 0.7335(5) 0.0587(9) Uani 1 1 d . . .
C5 C 0.9684(3) -0.06174(19) 0.7911(5) 0.0641(10) Uani 1 1 d . . .
H5 H 0.9568 -0.1062 0.8211 0.077 Uiso 1 1 calc R . .
C6 C 1.0733(3) -0.03682(19) 0.8036(5) 0.0618(9) Uani 1 1 d . . .
C7 C 0.3507(4) 0.1817(3) 0.6761(8) 0.1017(16) Uani 1 1 d . . .
H7A H 0.3367 0.1698 0.5475 0.153 Uiso 1 1 calc R . .
H7B H 0.3678 0.2286 0.6879 0.153 Uiso 1 1 calc R . .
H7C H 0.2866 0.1723 0.7325 0.153 Uiso 1 1 calc R . .
C8 C 0.4741(5) 0.1466(3) 1.0308(6) 0.1027(16) Uani 1 1 d . . .
H8A H 0.4110 0.1276 1.0744 0.154 Uiso 1 1 calc R . .
H8B H 0.4775 0.1938 1.0573 0.154 Uiso 1 1 calc R . .
H8C H 0.5395 0.1252 1.0918 0.154 Uiso 1 1 calc R . .
C9 C 0.4414(4) 0.0476(2) 0.7414(7) 0.0929(15) Uani 1 1 d . . .
H9A H 0.4334 0.0401 0.6103 0.139 Uiso 1 1 calc R . .
H9B H 0.3759 0.0334 0.7870 0.139 Uiso 1 1 calc R . .
H9C H 0.5031 0.0224 0.8016 0.139 Uiso 1 1 calc R . .
C10 C 0.5905(3) 0.1575(2) 0.7145(5) 0.0640(10) Uani 1 1 d . . .
H10 H 0.6484 0.1292 0.7814 0.077 Uiso 1 1 calc R . .
C11 C 0.5923(4) 0.1475(2) 0.5078(6) 0.0856(13) Uani 1 1 d . . .
H11A H 0.6188 0.1030 0.4837 0.103 Uiso 1 1 calc R . .
H11B H 0.5193 0.1532 0.4384 0.103 Uiso 1 1 calc R . .
C12 C 0.6683(6) 0.1997(3) 0.4567(9) 0.124(2) Uani 1 1 d . . .
H12A H 0.7351 0.1789 0.4281 0.148 Uiso 1 1 calc R . .
H12B H 0.6341 0.2238 0.3480 0.148 Uiso 1 1 calc R . .
C13 C 0.6936(8) 0.2441(4) 0.6051(13) 0.204(5) Uani 1 1 d . . .
H13A H 0.6814 0.2898 0.5615 0.244 Uiso 1 1 calc R . .
H13B H 0.7706 0.2396 0.6569 0.244 Uiso 1 1 calc R . .
C14 C 0.6248(5) 0.2303(3) 0.7494(8) 0.1088(19) Uani 1 1 d . . .
H14A H 0.5612 0.2596 0.7367 0.131 Uiso 1 1 calc R . .
H14B H 0.6665 0.2359 0.8719 0.131 Uiso 1 1 calc R . .
N1 N 1.0111(4) 0.1399(2) 0.6432(8) 0.0942(13) Uani 1 1 d . . .
N2 N 0.7695(3) -0.04532(19) 0.7215(5) 0.0748(10) Uani 1 1 d . . .
N3 N 1.1636(3) -0.0831(2) 0.8644(6) 0.0869(11) Uani 1 1 d . . .
O1 O 1.1916(2) 0.05720(19) 0.7853(7) 0.1302(16) Uani 1 1 d . . .
O4 O 0.6927(2) -0.00647(18) 0.6870(5) 0.1017(11) Uani 1 1 d . . .
O5 O 0.7565(3) -0.10558(17) 0.7437(6) 0.1091(12) Uani 1 1 d . . .
O6 O 1.1436(4) -0.1366(2) 0.9245(9) 0.166(2) Uani 1 1 d . . .
O7 O 1.2546(3) -0.0683(2) 0.8623(9) 0.165(2) Uani 1 1 d . . .
O2A O 1.0841(15) 0.1709(7) 0.705(3) 0.183(8) Uani 0.50 1 d P . .
O3A O 0.9446(10) 0.1822(4) 0.702(3) 0.218(8) Uani 0.50 1 d P . .
O2B O 1.0879(13) 0.1583(7) 0.5901(15) 0.119(4) Uani 0.50 1 d P . .
O3B O 0.9441(7) 0.1611(4) 0.5139(12) 0.102(2) Uani 0.50 1 d P . .
P1 P 0.46347(8) 0.13412(5) 0.78797(14) 0.0628(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.234(5) . ?
C1 C6 1.448(6) . ?
C1 C2 1.455(5) . ?
C2 C3 1.361(5) . ?
C2 N1 1.458(5) . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(5) . ?
C4 N2 1.441(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 N3 1.462(5) . ?
C7 P1 1.776(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 P1 1.778(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 P1 1.771(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C14 1.524(6) . ?
C10 C11 1.527(6) . ?
C10 P1 1.788(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.484(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.400(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.473(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 O2A 1.128(14) . ?
N1 O2B 1.135(14) . ?
N1 O3B 1.232(8) . ?
N1 O3A 1.293(12) . ?
N2 O4 1.219(4) . ?
N2 O5 1.226(5) . ?
N3 O7 1.161(5) . ?
N3 O6 1.193(5) . ?
O2A O2B 0.89(2) . ?
O2A O3A 1.73(2) . ?
O3A O3B 1.440(19) . ?
O2B O3B 1.775(18) . ?

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 C1 C6 125.7(4) . . ?
O1 C1 C2 122.7(4) . . ?
C6 C1 C2 111.6(3) . . ?
C3 C2 C1 124.3(4) . . ?
C3 C2 N1 116.9(4) . . ?
C1 C2 N1 118.9(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 N2 119.1(3) . . ?
C5 C4 N2 120.0(3) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 124.0(3) . . ?
C5 C6 N3 117.1(4) . . ?
C1 C6 N3 118.9(3) . . ?
P1 C7 H7A 109.5 . . ?
P1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
P1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
P1 C8 H8A 109.5 . . ?
P1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
P1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
P1 C9 H9A 109.5 . . ?
P1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
P1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C10 C11 104.2(4) . . ?
C14 C10 P1 115.5(3) . . ?
C11 C10 P1 113.9(3) . . ?
C14 C10 H10 107.6 . . ?
C11 C10 H10 107.6 . . ?
P1 C10 H10 107.6 . . ?
C12 C11 C10 105.0(4) . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C13 C12 C11 108.9(5) . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 C14 110.6(5) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C10 103.5(4) . . ?
C13 C14 H14A 111.1 . . ?
C10 C14 H14A 111.1 . . ?
C13 C14 H14B 111.1 . . ?
C10 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
O2A N1 O2B 46.1(11) . . ?
O2A N1 O3B 121.5(10) . . ?
O2B N1 O3B 97.1(9) . . ?
O2A N1 O3A 90.8(12) . . ?
O2B N1 O3A 120.2(10) . . ?
O3B N1 O3A 69.5(9) . . ?
O2A N1 C2 120.6(10) . . ?
O2B N1 C2 121.5(9) . . ?
O3B N1 C2 117.5(5) . . ?
O3A N1 C2 115.8(7) . . ?
O4 N2 O5 122.6(3) . . ?
O4 N2 C4 119.1(3) . . ?
O5 N2 C4 118.3(4) . . ?
O7 N3 O6 119.0(5) . . ?
O7 N3 C6 121.7(4) . . ?
O6 N3 C6 119.2(4) . . ?
O2B O2A N1 67.3(14) . . ?
O2B O2A O3A 103(2) . . ?
N1 O2A O3A 48.4(9) . . ?
N1 O3A O3B 53.3(7) . . ?
N1 O3A O2A 40.8(6) . . ?
O3B O3A O2A 80.6(10) . . ?
O2A O2B N1 66.6(17) . . ?
O2A O2B O3B 96(2) . . ?
N1 O2B O3B 43.6(7) . . ?
N1 O3B O3A 57.2(6) . . ?
N1 O3B O2B 39.4(5) . . ?
O3A O3B O2B 81.1(8) . . ?
C9 P1 C7 110.1(2) . . ?
C9 P1 C8 108.4(3) . . ?
C7 P1 C8 108.7(3) . . ?
C9 P1 C10 108.16(19) . . ?
C7 P1 C10 112.4(2) . . ?
C8 P1 C10 109.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -174.9(5) . . . . ?
C6 C1 C2 C3 3.6(6) . . . . ?
O1 C1 C2 N1 5.0(7) . . . . ?
C6 C1 C2 N1 -176.4(4) . . . . ?
C1 C2 C3 C4 -2.1(6) . . . . ?
N1 C2 C3 C4 177.9(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 N2 179.6(4) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
N2 C4 C5 C6 -179.4(3) . . . . ?
C4 C5 C6 C1 1.7(6) . . . . ?
C4 C5 C6 N3 -179.8(3) . . . . ?
O1 C1 C6 C5 175.1(5) . . . . ?
C2 C1 C6 C5 -3.4(6) . . . . ?
O1 C1 C6 N3 -3.4(7) . . . . ?
C2 C1 C6 N3 178.0(3) . . . . ?
C14 C10 C11 C12 23.3(6) . . . . ?
P1 C10 C11 C12 150.1(4) . . . . ?
C10 C11 C12 C13 -10.0(8) . . . . ?
C11 C12 C13 C14 -8.2(11) . . . . ?
C12 C13 C14 C10 22.7(10) . . . . ?
C11 C10 C14 C13 -27.6(7) . . . . ?
P1 C10 C14 C13 -153.3(6) . . . . ?
C3 C2 N1 O2A 152.0(14) . . . . ?
C1 C2 N1 O2A -27.9(15) . . . . ?
C3 C2 N1 O2B -153.7(9) . . . . ?
C1 C2 N1 O2B 26.4(11) . . . . ?
C3 C2 N1 O3B -34.9(8) . . . . ?
C1 C2 N1 O3B 145.2(6) . . . . ?
C3 C2 N1 O3A 44.3(12) . . . . ?
C1 C2 N1 O3A -135.6(11) . . . . ?
C3 C4 N2 O4 -6.4(6) . . . . ?
C5 C4 N2 O4 173.3(4) . . . . ?
C3 C4 N2 O5 172.5(4) . . . . ?
C5 C4 N2 O5 -7.8(6) . . . . ?
C5 C6 N3 O7 172.6(5) . . . . ?
C1 C6 N3 O7 -8.7(7) . . . . ?
C5 C6 N3 O6 -10.3(7) . . . . ?
C1 C6 N3 O6 168.3(5) . . . . ?
O3B N1 O2A O2B -67(2) . . . . ?
O3A N1 O2A O2B -133(2) . . . . ?
C2 N1 O2A O2B 105.8(19) . . . . ?
O2B N1 O2A O3A 133(2) . . . . ?
O3B N1 O2A O3A 66.3(11) . . . . ?
C2 N1 O2A O3A -120.9(13) . . . . ?
O2A N1 O3A O3B 123.6(12) . . . . ?
O2B N1 O3A O3B 86.2(12) . . . . ?
C2 N1 O3A O3B -111.6(8) . . . . ?
O2B N1 O3A O2A -37.4(14) . . . . ?
O3B N1 O3A O2A -123.6(12) . . . . ?
C2 N1 O3A O2A 124.9(14) . . . . ?
O2B O2A O3A N1 43.5(16) . . . . ?
O2B O2A O3A O3B 0.9(19) . . . . ?
N1 O2A O3A O3B -42.6(9) . . . . ?
O3A O2A O2B N1 -33.9(10) . . . . ?
N1 O2A O2B O3B 33.2(7) . . . . ?
O3A O2A O2B O3B -0.7(16) . . . . ?
O3B N1 O2B O2A 127.7(18) . . . . ?
O3A N1 O2B O2A 57(2) . . . . ?
C2 N1 O2B O2A -103.8(19) . . . . ?
O2A N1 O2B O3B -127.7(18) . . . . ?
O3A N1 O2B O3B -70.3(12) . . . . ?
C2 N1 O2B O3B 128.5(10) . . . . ?
O2A N1 O3B O3A -77.7(15) . . . . ?
O2B N1 O3B O3A -119.7(10) . . . . ?
C2 N1 O3B O3A 109.2(7) . . . . ?
O2A N1 O3B O2B 41.9(15) . . . . ?
O3A N1 O3B O2B 119.7(10) . . . . ?
C2 N1 O3B O2B -131.1(11) . . . . ?
O2A O3A O3B N1 33.5(6) . . . . ?
N1 O3A O3B O2B -33.9(5) . . . . ?
O2A O3A O3B O2B -0.4(10) . . . . ?
O2A O2B O3B N1 -46.8(15) . . . . ?
O2A O2B O3B O3A 0.9(18) . . . . ?
N1 O2B O3B O3A 47.7(8) . . . . ?
C14 C10 P1 C9 -178.2(4) . . . . ?
C11 C10 P1 C9 61.1(4) . . . . ?
C14 C10 P1 C7 60.0(4) . . . . ?
C11 C10 P1 C7 -60.7(4) . . . . ?
C14 C10 P1 C8 -60.6(4) . . . . ?
C11 C10 P1 C8 178.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9C O4 0.96 2.66 3.352(5) 129.8 .
C9 H9B O7 0.96 2.62 3.465(7) 146.5 1_455
C9 H9B O1 0.96 2.31 3.142(5) 144.1 1_455
C9 H9A O4 0.96 2.56 3.415(6) 147.8 3_656
C8 H8A O5 0.96 2.65 3.581(6) 163.7 3_657
C7 H7C O2B 0.96 2.53 3.233(16) 130.5 1_455
C7 H7C O2A 0.96 2.47 3.32(2) 148.2 1_455
C7 H7C O1 0.96 2.63 3.330(6) 130.0 1_455
C7 H7A O5 0.96 2.60 3.501(7) 156.4 3_656
C9 H9C O4 0.96 2.66 3.352(5) 129.8 .
C9 H9B O7 0.96 2.62 3.465(7) 146.5 1_455
C9 H9B O1 0.96 2.31 3.142(5) 144.1 1_455
C9 H9A O4 0.96 2.56 3.415(6) 147.8 3_656
C7 H7C O2B 0.96 2.53 3.233(16) 130.5 1_455
C7 H7C O2A 0.96 2.47 3.32(2) 148.2 1_455
C7 H7C O1 0.96 2.63 3.330(6) 130.0 1_455
C7 H7A O5 0.96 2.60 3.501(7) 156.4 3_656
C8 H8A O5 0.96 2.65 3.581(6) 163.7 3_657
C9 H9C O4 0.96 2.66 3.352(5) 129.8 .
C9 H9B O7 0.96 2.62 3.465(7) 146.5 1_455
C9 H9B O1 0.96 2.31 3.142(5) 144.1 1_455
C9 H9A O4 0.96 2.56 3.415(6) 147.8 3_656
C7 H7C O2B 0.96 2.53 3.233(16) 130.5 1_455
C7 H7C O2A 0.96 2.47 3.32(2) 148.2 1_455
C7 H7C O1 0.96 2.63 3.330(6) 130.0 1_455
C7 H7A O5 0.96 2.60 3.501(7) 156.4 3_656
C8 H8A O5 0.96 2.65 3.581(6) 163.7 3_657
C8 H8A O5 0.96 2.65 3.581(6) 163.7 3_657
C7 H7A O5 0.96 2.60 3.501(7) 156.4 3_656
C7 H7C O1 0.96 2.63 3.330(6) 130.0 1_455
C7 H7C O2A 0.96 2.47 3.32(2) 148.2 1_455
C7 H7C O2B 0.96 2.53 3.233(16) 130.5 1_455
C9 H9A O4 0.96 2.56 3.415(6) 147.8 3_656
C9 H9B O1 0.96 2.31 3.142(5) 144.1 1_455
C9 H9B O7 0.96 2.62 3.465(7) 146.5 1_455
C9 H9C O4 0.96 2.66 3.352(5) 129.8 .
C7 H7A O5 0.96 2.60 3.501(7) 156.4 3_656
C7 H7C O1 0.96 2.63 3.330(6) 130.0 1_455
C7 H7C O2A 0.96 2.47 3.32(2) 148.2 1_455
C7 H7C O2B 0.96 2.53 3.233(16) 130.5 1_455
C8 H8A O5 0.96 2.65 3.581(6) 163.7 3_657
C9 H9A O4 0.96 2.56 3.415(6) 147.8 3_656
C9 H9B O1 0.96 2.31 3.142(5) 144.1 1_455
C9 H9B O7 0.96 2.62 3.465(7) 146.5 1_455
C9 H9C O4 0.96 2.66 3.352(5) 129.8 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.064
