# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_293K
_database_code_depnum_ccdc_archive 'CCDC 1866561'
_audit_update_record             
;
2018-09-08 deposited with the CCDC.
2018-10-26 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 P'
_chemical_formula_sum            'C10 H14 N3 O7 P'
_chemical_formula_weight         319.21

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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_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                   19.532(7)
_cell_length_b                   11.187(2)
_cell_length_c                   27.511(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.54(4)
_cell_angle_gamma                90.00
_cell_volume                     6000(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1930
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2656
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15378
_diffrn_reflns_av_R_equivalents  0.1415
_diffrn_reflns_av_sigmaI/netI    0.1427
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5265
_reflns_number_gt                1930
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5265
_refine_ls_number_parameters     387
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2812
_refine_ls_R_factor_gt           0.1417
_refine_ls_wR_factor_ref         0.4423
_refine_ls_wR_factor_gt          0.3745
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0685(3) 1.1830(6) 0.1727(2) 0.106(2) Uani 1 1 d . . .
O2 O -0.0511(4) 1.2773(7) 0.1937(4) 0.168(3) Uani 1 1 d U . .
O3 O -0.1330(4) 1.1954(7) 0.1716(4) 0.169(4) Uani 1 1 d . . .
O4 O -0.1354(3) 0.7684(7) 0.2092(2) 0.125(3) Uani 1 1 d . . .
O5 O -0.0420(4) 0.6651(7) 0.1979(3) 0.137(3) Uani 1 1 d . . .
O6 O 0.1653(3) 0.8775(6) 0.1568(3) 0.122(3) Uani 1 1 d . . .
O7 O 0.1780(3) 1.0316(7) 0.2011(3) 0.133(3) Uani 1 1 d . . .
N1 N -0.0761(5) 1.1892(8) 0.1820(4) 0.137(3) Uani 1 1 d U . .
N2 N -0.0763(4) 0.7590(7) 0.1996(3) 0.089(2) Uani 1 1 d . . .
N3 N 0.1417(4) 0.9619(7) 0.1790(3) 0.089(2) Uani 1 1 d . . .
C1 C 0.0369(3) 1.0868(4) 0.1810(2) 0.064(2) Uani 1 1 d D . .
C2 C -0.0345(4) 1.0836(8) 0.1862(3) 0.077(3) Uani 1 1 d . . .
C3 C -0.0740(4) 0.9806(8) 0.1912(3) 0.075(3) Uani 1 1 d . . .
H3 H -0.1214 0.9835 0.1929 0.090 Uiso 1 1 calc R . .
C4 C -0.0372(4) 0.8718(8) 0.1934(3) 0.078(3) Uani 1 1 d . . .
C5 C 0.0327(3) 0.8705(5) 0.1871(3) 0.081(3) Uani 1 1 d D . .
H5 H 0.0556 0.7978 0.1856 0.097 Uiso 1 1 calc R . .
C6 C 0.0687(3) 0.9757(4) 0.1831(2) 0.066(2) Uani 1 1 d D . .
O8 O 0.4258(3) 0.2524(5) 0.0760(2) 0.093(2) Uani 1 1 d . . .
O14 O 0.5575(4) 0.1635(6) 0.0924(3) 0.146(3) Uani 1 1 d . . .
O13 O 0.6211(3) 0.2362(6) 0.0408(3) 0.130(3) Uani 1 1 d . . .
O12 O 0.6317(3) 0.6672(6) 0.0460(2) 0.106(2) Uani 1 1 d . . .
O11 O 0.5364(3) 0.7684(5) 0.0465(2) 0.103(2) Uani 1 1 d . . .
O10 O 0.3235(4) 0.5530(7) 0.0518(3) 0.150(3) Uani 1 1 d . . .
O9 O 0.3243(3) 0.4036(7) 0.0971(3) 0.141(3) Uani 1 1 d . . .
N4 N 0.5741(4) 0.2430(6) 0.0659(3) 0.088(2) Uani 1 1 d . . .
N5 N 0.5666(4) 0.6737(7) 0.0488(2) 0.081(2) Uani 1 1 d . . .
N6 N 0.3546(4) 0.4750(7) 0.0720(3) 0.088(2) Uani 1 1 d . . .
C7 C 0.4589(2) 0.3478(7) 0.0717(3) 0.065(2) Uani 1 1 d D . .
C12 C 0.5286(3) 0.3511(6) 0.0645(3) 0.070(2) Uani 1 1 d D . .
C11 C 0.5663(3) 0.4560(5) 0.0574(2) 0.066(2) Uani 1 1 d D . .
H11 H 0.6133 0.4527 0.0539 0.079 Uiso 1 1 calc R . .
C10 C 0.5321(3) 0.5637(5) 0.0557(2) 0.059(2) Uani 1 1 d DU . .
C9 C 0.4624(3) 0.5677(5) 0.0604(2) 0.067(2) Uani 1 1 d DU . .
H9A H 0.4397 0.6408 0.0589 0.080 Uiso 1 1 calc R . .
C8 C 0.4258(3) 0.4643(5) 0.0671(2) 0.063(2) Uani 1 1 d D . .
P1 P 0.33212(11) -0.00705(19) 0.06608(8) 0.0690(7) Uani 1 1 d . . .
C14 C 0.2893(4) -0.1437(8) 0.0620(4) 0.106(3) Uani 1 1 d . . .
H14A H 0.2951 -0.1849 0.0925 0.158 Uiso 1 1 calc R . .
H14B H 0.3078 -0.1914 0.0369 0.158 Uiso 1 1 calc R . .
H14C H 0.2413 -0.1301 0.0541 0.158 Uiso 1 1 calc R . .
C15 C 0.3225(8) 0.0637(14) 0.0104(4) 0.237(8) Uani 1 1 d . . .
H15A H 0.3014 0.1403 0.0144 0.356 Uiso 1 1 calc R . .
H15B H 0.2941 0.0159 -0.0116 0.356 Uiso 1 1 calc R . .
H15C H 0.3667 0.0743 -0.0024 0.356 Uiso 1 1 calc R . .
C16 C 0.4200(5) -0.0333(10) 0.0786(7) 0.243(10) Uani 1 1 d . . .
H16A H 0.4452 -0.0016 0.0526 0.365 Uiso 1 1 calc R . .
H16B H 0.4280 -0.1178 0.0813 0.365 Uiso 1 1 calc R . .
H16C H 0.4348 0.0051 0.1086 0.365 Uiso 1 1 calc R . .
P2 P 0.16059(11) 0.4536(2) 0.18611(9) 0.0728(7) Uani 1 1 d . . .
C19 C 0.2080(5) 0.5928(9) 0.1894(5) 0.147(5) Uani 1 1 d . . .
H19A H 0.2558 0.5769 0.1862 0.220 Uiso 1 1 calc R . .
H19B H 0.2021 0.6305 0.2202 0.220 Uiso 1 1 calc R . .
H19C H 0.1912 0.6448 0.1636 0.220 Uiso 1 1 calc R . .
C18 C 0.1551(6) 0.4013(12) 0.1271(4) 0.162(5) Uani 1 1 d . . .
H18A H 0.1897 0.3416 0.1234 0.242 Uiso 1 1 calc R . .
H18B H 0.1619 0.4662 0.1051 0.242 Uiso 1 1 calc R . .
H18C H 0.1106 0.3668 0.1199 0.242 Uiso 1 1 calc R . .
C17 C 0.2013(6) 0.3456(10) 0.2248(5) 0.197(6) Uani 1 1 d . . .
H17A H 0.1677 0.2901 0.2353 0.295 Uiso 1 1 calc R . .
H17B H 0.2233 0.3845 0.2526 0.295 Uiso 1 1 calc R . .
H17C H 0.2349 0.3033 0.2074 0.295 Uiso 1 1 calc R . .
C20 C 0.0763(5) 0.4810(9) 0.2030(4) 0.134(5) Uani 1 1 d . . .
H20A H 0.0536 0.5341 0.1798 0.201 Uiso 1 1 calc R . .
H20B H 0.0779 0.5170 0.2347 0.201 Uiso 1 1 calc R . .
H20C H 0.0516 0.4069 0.2037 0.201 Uiso 1 1 calc R . .
C13 C 0.3046(7) 0.0756(13) 0.1118(5) 0.274(7) Uani 1 1 d . . .
H13A H 0.3037 0.1584 0.1025 0.411 Uiso 1 1 calc R . .
H13B H 0.3351 0.0654 0.1402 0.411 Uiso 1 1 calc R . .
H13C H 0.2593 0.0505 0.1189 0.411 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
O1 C1 1.269(8) . ?
O2 N1 1.138(10) . ?
O3 N1 1.133(10) . ?
O4 N2 1.203(9) . ?
O5 N2 1.249(10) . ?
O6 N3 1.229(9) . ?
O7 N3 1.193(9) . ?
N1 C2 1.434(12) . ?
N2 C4 1.491(11) . ?
N3 C6 1.446(9) . ?
C1 C6 1.388(4) . ?
C1 C2 1.412(10) . ?
C2 C3 1.399(11) . ?
C3 C4 1.413(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(10) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
O8 C7 1.257(8) . ?
O14 N4 1.206(9) . ?
O13 N4 1.184(9) . ?
O12 N5 1.280(8) . ?
O11 N5 1.212(8) . ?
O10 N6 1.183(10) . ?
O9 N6 1.232(9) . ?
N4 C12 1.500(9) . ?
N5 C10 1.422(9) . ?
N6 C8 1.410(9) . ?
C7 C12 1.387(4) . ?
C7 C8 1.457(9) . ?
C12 C11 1.406(8) . ?
C11 C10 1.378(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.376(9) . ?
C9 C8 1.378(4) . ?
C9 H9A 0.9300 . ?
P1 C13 1.677(12) . ?
P1 C15 1.723(12) . ?
P1 C14 1.744(9) . ?
P1 C16 1.754(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
P2 C18 1.722(11) . ?
P2 C20 1.765(9) . ?
P2 C17 1.766(11) . ?
P2 C19 1.812(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N1 O2 114.5(10) . . ?
O3 N1 C2 127.9(9) . . ?
O2 N1 C2 117.4(9) . . ?
O4 N2 O5 127.3(8) . . ?
O4 N2 C4 117.1(8) . . ?
O5 N2 C4 115.3(7) . . ?
O7 N3 O6 121.7(8) . . ?
O7 N3 C6 116.7(7) . . ?
O6 N3 C6 121.4(7) . . ?
O1 C1 C6 123.1(6) . . ?
O1 C1 C2 122.3(6) . . ?
C6 C1 C2 114.5(6) . . ?
C3 C2 C1 125.8(8) . . ?
C3 C2 N1 111.9(8) . . ?
C1 C2 N1 122.0(8) . . ?
C2 C3 C4 115.6(7) . . ?
C2 C3 H3 122.2 . . ?
C4 C3 H3 122.2 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 N2 121.4(8) . . ?
C3 C4 N2 118.2(7) . . ?
C6 C5 C4 120.8(7) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 122.6(6) . . ?
C5 C6 N3 115.1(6) . . ?
C1 C6 N3 122.2(6) . . ?
O13 N4 O14 123.5(8) . . ?
O13 N4 C12 121.1(7) . . ?
O14 N4 C12 115.4(8) . . ?
O11 N5 O12 121.9(7) . . ?
O11 N5 C10 122.0(7) . . ?
O12 N5 C10 116.1(7) . . ?
O10 N6 O9 119.4(8) . . ?
O10 N6 C8 120.0(8) . . ?
O9 N6 C8 120.6(7) . . ?
O8 C7 C12 123.4(7) . . ?
O8 C7 C8 122.7(5) . . ?
C12 C7 C8 113.4(6) . . ?
C7 C12 C11 124.7(6) . . ?
C7 C12 N4 124.1(7) . . ?
C11 C12 N4 111.2(5) . . ?
C10 C11 C12 118.5(6) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C9 C10 C11 120.4(6) . . ?
C9 C10 N5 117.7(5) . . ?
C11 C10 N5 121.9(6) . . ?
C10 C9 C8 120.7(6) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C8 N6 117.7(6) . . ?
C9 C8 C7 122.1(6) . . ?
N6 C8 C7 120.1(5) . . ?
C13 P1 C15 113.0(8) . . ?
C13 P1 C14 111.0(6) . . ?
C15 P1 C14 108.6(6) . . ?
C13 P1 C16 107.5(8) . . ?
C15 P1 C16 107.6(8) . . ?
C14 P1 C16 109.0(5) . . ?
P1 C14 H14A 109.5 . . ?
P1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
P1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
P1 C15 H15A 109.5 . . ?
P1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
P1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
P1 C16 H16A 109.5 . . ?
P1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
P1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 P2 C20 107.6(6) . . ?
C18 P2 C17 109.5(6) . . ?
C20 P2 C17 110.6(6) . . ?
C18 P2 C19 110.0(6) . . ?
C20 P2 C19 108.6(5) . . ?
C17 P2 C19 110.4(5) . . ?
P2 C19 H19A 109.5 . . ?
P2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
P2 C18 H18A 109.5 . . ?
P2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
P2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
P2 C17 H17A 109.5 . . ?
P2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
P2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
P2 C20 H20A 109.5 . . ?
P2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
P2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
P1 C13 H13A 109.5 . . ?
P1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
P1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 174.0(7) . . . . ?
C6 C1 C2 C3 -2.6(11) . . . . ?
O1 C1 C2 N1 0.6(12) . . . . ?
C6 C1 C2 N1 -176.0(8) . . . . ?
O3 N1 C2 C3 -18.9(16) . . . . ?
O2 N1 C2 C3 154.7(10) . . . . ?
O3 N1 C2 C1 155.3(12) . . . . ?
O2 N1 C2 C1 -31.0(15) . . . . ?
C1 C2 C3 C4 3.3(11) . . . . ?
N1 C2 C3 C4 177.3(7) . . . . ?
C2 C3 C4 C5 -4.8(10) . . . . ?
C2 C3 C4 N2 178.8(6) . . . . ?
O4 N2 C4 C5 173.5(7) . . . . ?
O5 N2 C4 C5 -1.1(11) . . . . ?
O4 N2 C4 C3 -10.1(10) . . . . ?
O5 N2 C4 C3 175.2(7) . . . . ?
C3 C4 C5 C6 5.9(11) . . . . ?
N2 C4 C5 C6 -177.8(7) . . . . ?
C4 C5 C6 C1 -5.4(11) . . . . ?
C4 C5 C6 N3 177.1(7) . . . . ?
O1 C1 C6 C5 -173.1(7) . . . . ?
C2 C1 C6 C5 3.5(10) . . . . ?
O1 C1 C6 N3 4.2(11) . . . . ?
C2 C1 C6 N3 -179.1(6) . . . . ?
O7 N3 C6 C5 -139.5(8) . . . . ?
O6 N3 C6 C5 35.5(11) . . . . ?
O7 N3 C6 C1 42.9(11) . . . . ?
O6 N3 C6 C1 -142.0(8) . . . . ?
O8 C7 C12 C11 177.0(7) . . . . ?
C8 C7 C12 C11 4.8(10) . . . . ?
O8 C7 C12 N4 -6.1(12) . . . . ?
C8 C7 C12 N4 -178.3(6) . . . . ?
O13 N4 C12 C7 146.8(8) . . . . ?
O14 N4 C12 C7 -30.1(11) . . . . ?
O13 N4 C12 C11 -36.0(11) . . . . ?
O14 N4 C12 C11 147.2(8) . . . . ?
C7 C12 C11 C10 -2.2(11) . . . . ?
N4 C12 C11 C10 -179.4(6) . . . . ?
C12 C11 C10 C9 -0.7(10) . . . . ?
C12 C11 C10 N5 179.8(6) . . . . ?
O11 N5 C10 C9 -0.7(10) . . . . ?
O12 N5 C10 C9 178.0(6) . . . . ?
O11 N5 C10 C11 178.8(7) . . . . ?
O12 N5 C10 C11 -2.5(10) . . . . ?
C11 C10 C9 C8 0.5(11) . . . . ?
N5 C10 C9 C8 179.9(6) . . . . ?
C10 C9 C8 N6 179.6(7) . . . . ?
C10 C9 C8 C7 2.6(11) . . . . ?
O10 N6 C8 C9 30.8(12) . . . . ?
O9 N6 C8 C9 -149.2(8) . . . . ?
O10 N6 C8 C7 -152.2(8) . . . . ?
O9 N6 C8 C7 27.8(12) . . . . ?
O8 C7 C8 C9 -177.3(7) . . . . ?
C12 C7 C8 C9 -5.0(10) . . . . ?
O8 C7 C8 N6 5.8(11) . . . . ?
C12 C7 C8 N6 178.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.089
# start Validation Reply Form
_vrf_PLAT026_1_293K              
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check 
RESPONSE: This compound undergoes structural phase transition near room 
temperature (305/293 K). The molecules are usually disordered near phase
transition temperature, which might cause the weak diffraction.   
;
_vrf_PLAT084_1_293K              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.44 Report
RESPONSE: As the measured temperature is near phase transition temperature, 
the thermal vibrations of many atoms are intense, the data quality is not 
very good.
;
# 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_293K
_database_code_depnum_ccdc_archive 'CCDC 1866562'
_audit_update_record             
;
2018-09-08 deposited with the CCDC.
2018-10-26 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, C6 H16 P'
_chemical_formula_sum            'C12 H18 N3 O7 P'
_chemical_formula_weight         347.26

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                   7.0034(14)
_cell_length_b                   19.672(4)
_cell_length_c                   12.380(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.85(3)
_cell_angle_gamma                90.00
_cell_volume                     1640.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2578
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10877
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3730
_reflns_number_gt                2578
_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)+(0.0809P)²+0.6637P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3730
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2043
_refine_ls_wR_factor_gt          0.1878
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_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 0.84012(13) 1.35523(4) 1.53689(7) 0.0483(3) Uani 1 1 d . . .
C8 C 0.7557(7) 1.44045(18) 1.5413(3) 0.0710(11) Uani 1 1 d . . .
H8A H 0.6199 1.4401 1.5437 0.107 Uiso 1 1 calc R . .
H8B H 0.7659 1.4644 1.4756 0.107 Uiso 1 1 calc R . .
H8C H 0.8360 1.4627 1.6071 0.107 Uiso 1 1 calc R . .
C11 C 0.4853(6) 1.32182(19) 1.3795(3) 0.0634(10) Uani 1 1 d . . .
H11A H 0.4420 1.3093 1.4448 0.076 Uiso 1 1 calc R . .
H11B H 0.4483 1.3689 1.3618 0.076 Uiso 1 1 calc R . .
C7 C 1.0994(6) 1.3566(2) 1.5472(4) 0.0777(12) Uani 1 1 d . . .
H7A H 1.1694 1.3787 1.6157 0.117 Uiso 1 1 calc R . .
H7B H 1.1213 1.3809 1.4844 0.117 Uiso 1 1 calc R . .
H7C H 1.1470 1.3108 1.5470 0.117 Uiso 1 1 calc R . .
C10 C 0.7091(5) 1.31555(19) 1.4078(3) 0.0581(9) Uani 1 1 d . . .
H10A H 0.7537 1.3355 1.3473 0.070 Uiso 1 1 calc R . .
H10B H 0.7437 1.2677 1.4117 0.070 Uiso 1 1 calc R . .
C9 C 0.7975(7) 1.3081(2) 1.6500(3) 0.0716(11) Uani 1 1 d . . .
H9A H 0.8696 1.3284 1.7198 0.107 Uiso 1 1 calc R . .
H9B H 0.8417 1.2621 1.6467 0.107 Uiso 1 1 calc R . .
H9C H 0.6582 1.3082 1.6448 0.107 Uiso 1 1 calc R . .
C12 C 0.3793(7) 1.2776(2) 1.2816(4) 0.0856(13) Uani 1 1 d . . .
H12A H 0.4320 1.2862 1.2190 0.128 Uiso 1 1 calc R . .
H12B H 0.2400 1.2879 1.2609 0.128 Uiso 1 1 calc R . .
H12C H 0.3987 1.2306 1.3028 0.128 Uiso 1 1 calc R . .
O1 O 0.9510(4) 1.56805(13) 1.20884(19) 0.0648(7) Uani 1 1 d . . .
C4 C 0.6532(4) 1.48768(17) 0.9037(2) 0.0445(7) Uani 1 1 d . . .
C1 C 0.8670(4) 1.54252(16) 1.1172(3) 0.0430(7) Uani 1 1 d . . .
C5 C 0.6712(5) 1.55766(16) 0.9169(3) 0.0453(8) Uani 1 1 d . . .
H5 H 0.6131 1.5867 0.8578 0.054 Uiso 1 1 calc R . .
C2 C 0.8376(4) 1.47052(16) 1.0944(2) 0.0422(7) Uani 1 1 d . . .
N2 N 0.5462(4) 1.46016(18) 0.7958(2) 0.0574(8) Uani 1 1 d . . .
O5 O 0.4723(5) 1.49984(16) 0.7190(2) 0.0832(9) Uani 1 1 d . . .
C6 C 0.7759(5) 1.58274(16) 1.0181(3) 0.0457(8) Uani 1 1 d . . .
C3 C 0.7357(5) 1.44438(16) 0.9910(3) 0.0455(7) Uani 1 1 d . . .
H3 H 0.7231 1.3976 0.9806 0.055 Uiso 1 1 calc R . .
N1 N 0.9143(5) 1.42192(16) 1.1830(3) 0.0584(8) Uani 1 1 d . . .
O4 O 0.5301(4) 1.39852(16) 0.7842(2) 0.0804(9) Uani 1 1 d . . .
N3 N 0.7925(6) 1.65637(16) 1.0269(2) 0.0656(9) Uani 1 1 d . . .
O6 O 0.6421(6) 1.69009(15) 0.9874(3) 0.1010(11) Uani 1 1 d . . .
O2 O 1.0246(7) 1.43861(17) 1.2690(3) 0.1269(16) Uani 1 1 d . . .
O3 O 0.8687(7) 1.36383(17) 1.1679(3) 0.1351(17) Uani 1 1 d . . .
O7 O 0.9512(6) 1.68107(16) 1.0723(3) 0.1051(12) 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
P1 C9 1.772(4) . ?
P1 C8 1.783(4) . ?
P1 C7 1.786(4) . ?
P1 C10 1.790(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 C12 1.512(5) . ?
C11 C10 1.515(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O1 C1 1.234(4) . ?
C4 C3 1.374(4) . ?
C4 C5 1.388(4) . ?
C4 N2 1.446(4) . ?
C1 C2 1.448(4) . ?
C1 C6 1.452(4) . ?
C5 C6 1.360(4) . ?
C5 H5 0.9300 . ?
C2 C3 1.383(4) . ?
C2 N1 1.443(4) . ?
N2 O4 1.223(4) . ?
N2 O5 1.230(4) . ?
C6 N3 1.455(4) . ?
C3 H3 0.9300 . ?
N1 O2 1.179(4) . ?
N1 O3 1.188(4) . ?
N3 O7 1.202(4) . ?
N3 O6 1.228(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
C9 P1 C8 109.8(2) . . ?
C9 P1 C7 109.8(2) . . ?
C8 P1 C7 108.9(2) . . ?
C9 P1 C10 108.75(19) . . ?
C8 P1 C10 110.14(18) . . ?
C7 P1 C10 109.48(19) . . ?
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 . . ?
C12 C11 C10 112.9(3) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
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 . . ?
C11 C10 P1 114.6(2) . . ?
C11 C10 H10A 108.6 . . ?
P1 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
P1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
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 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 N2 119.7(3) . . ?
C5 C4 N2 119.2(3) . . ?
O1 C1 C2 125.7(3) . . ?
O1 C1 C6 123.0(3) . . ?
C2 C1 C6 111.2(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C3 C2 N1 116.6(3) . . ?
C3 C2 C1 123.6(3) . . ?
N1 C2 C1 119.8(3) . . ?
O4 N2 O5 122.2(3) . . ?
O4 N2 C4 119.2(3) . . ?
O5 N2 C4 118.6(3) . . ?
C5 C6 C1 125.6(3) . . ?
C5 C6 N3 116.3(3) . . ?
C1 C6 N3 118.1(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O2 N1 O3 119.5(3) . . ?
O2 N1 C2 121.2(3) . . ?
O3 N1 C2 119.3(3) . . ?
O7 N3 O6 123.4(4) . . ?
O7 N3 C6 118.8(3) . . ?
O6 N3 C6 117.7(4) . . ?

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
C12 C11 C10 P1 -169.8(3) . . . . ?
C9 P1 C10 C11 69.9(3) . . . . ?
C8 P1 C10 C11 -50.4(3) . . . . ?
C7 P1 C10 C11 -170.1(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
N2 C4 C5 C6 -178.6(3) . . . . ?
O1 C1 C2 C3 177.5(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
O1 C1 C2 N1 -1.5(5) . . . . ?
C6 C1 C2 N1 -178.9(3) . . . . ?
C3 C4 N2 O4 0.3(5) . . . . ?
C5 C4 N2 O4 -179.9(3) . . . . ?
C3 C4 N2 O5 179.5(3) . . . . ?
C5 C4 N2 O5 -0.7(5) . . . . ?
C4 C5 C6 C1 -2.3(5) . . . . ?
C4 C5 C6 N3 179.2(3) . . . . ?
O1 C1 C6 C5 -175.8(3) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
O1 C1 C6 N3 2.7(5) . . . . ?
C2 C1 C6 N3 -179.8(3) . . . . ?
C5 C4 C3 C2 0.5(5) . . . . ?
N2 C4 C3 C2 -179.8(3) . . . . ?
N1 C2 C3 C4 178.0(3) . . . . ?
C1 C2 C3 C4 -1.1(5) . . . . ?
C3 C2 N1 O2 169.9(4) . . . . ?
C1 C2 N1 O2 -11.0(5) . . . . ?
C3 C2 N1 O3 -8.5(5) . . . . ?
C1 C2 N1 O3 170.6(4) . . . . ?
C5 C6 N3 O7 -135.5(4) . . . . ?
C1 C6 N3 O7 45.8(5) . . . . ?
C5 C6 N3 O6 44.6(5) . . . . ?
C1 C6 N3 O6 -134.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.264
_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_4_293K
_database_code_depnum_ccdc_archive 'CCDC 1866563'
_audit_update_record             
;
2018-09-08 deposited with the CCDC.
2018-10-26 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, C6 H14 P'
_chemical_formula_sum            'C12 H16 N3 O7 P'
_chemical_formula_weight         345.25

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           orthorhombic
_symmetry_space_group_name_H-M   'P c a b'
_symmetry_space_group_name_HALL  '-P 2bc 2ac'

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

_cell_length_a                   7.0408(14)
_cell_length_b                   19.834(4)
_cell_length_c                   23.634(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3300.4(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2127
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      25.99

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_T_max  0.9641
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18712
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3242
_reflns_number_gt                2127
_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)+(0.0809P)²+5.3362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     211
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1474
_refine_ls_R_factor_gt           0.0995
_refine_ls_wR_factor_ref         0.2374
_refine_ls_wR_factor_gt          0.2107
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.149
_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
C11 C 0.4979(11) 0.9340(7) 0.1918(3) 0.168(5) Uani 1 1 d D . .
H11 H 0.5328 0.8888 0.1935 0.202 Uiso 1 1 calc R . .
C12 C 0.6360(13) 0.9667(6) 0.2034(3) 0.153(4) Uani 1 1 d D . .
H12A H 0.6291 1.0135 0.2040 0.183 Uiso 1 1 calc R . .
H12B H 0.7500 0.9452 0.2118 0.183 Uiso 1 1 calc R . .
O1 O 0.2931(6) 0.82008(18) 0.47830(14) 0.0709(11) Uani 1 1 d . . .
N1 N 0.3061(6) 0.6741(2) 0.4691(2) 0.0553(11) Uani 1 1 d . . .
C2 C 0.3493(6) 0.7211(2) 0.42279(18) 0.0411(10) Uani 1 1 d . . .
C5 C 0.4400(6) 0.8038(3) 0.33151(19) 0.0482(12) Uani 1 1 d . . .
H5 H 0.4740 0.8311 0.3012 0.058 Uiso 1 1 calc R . .
C6 C 0.3873(6) 0.8320(2) 0.38184(19) 0.0449(11) Uani 1 1 d . . .
N3 N 0.3844(8) 0.9055(2) 0.3846(2) 0.0701(13) Uani 1 1 d . . .
C4 C 0.4426(6) 0.7338(3) 0.32594(19) 0.0492(12) Uani 1 1 d . . .
C3 C 0.3960(6) 0.6925(2) 0.3720(2) 0.0473(12) Uani 1 1 d . . .
H3 H 0.3969 0.6458 0.3680 0.057 Uiso 1 1 calc R . .
C1 C 0.3378(6) 0.7938(2) 0.43299(19) 0.0434(11) Uani 1 1 d . . .
N2 N 0.4969(6) 0.7037(3) 0.2729(2) 0.0686(13) Uani 1 1 d . . .
O5 O 0.5477(7) 0.7409(3) 0.23364(17) 0.0939(15) Uani 1 1 d . . .
O4 O 0.4936(8) 0.6419(3) 0.2684(2) 0.1087(17) Uani 1 1 d . . .
O3 O 0.2680(7) 0.6158(2) 0.4576(2) 0.0951(15) Uani 1 1 d . . .
O7 O 0.2709(9) 0.9335(2) 0.4151(2) 0.1154(19) Uani 1 1 d . . .
O6 O 0.4958(8) 0.9358(2) 0.3535(2) 0.1091(17) Uani 1 1 d . . .
O2 O 0.3110(7) 0.6942(2) 0.51792(17) 0.0886(14) Uani 1 1 d . . .
P1 P 0.2601(2) 0.89695(7) 0.10889(6) 0.0558(4) Uani 1 1 d . . .
C10 C 0.3020(8) 0.9363(3) 0.1766(2) 0.0749(18) Uani 1 1 d D . .
H10A H 0.2606 0.9830 0.1750 0.090 Uiso 1 1 calc R . .
H10B H 0.2276 0.9135 0.2053 0.090 Uiso 1 1 calc R . .
C9 C 0.3515(10) 0.8130(3) 0.1105(2) 0.0832(19) Uani 1 1 d . . .
H9A H 0.3228 0.7908 0.0754 0.125 Uiso 1 1 calc R . .
H9B H 0.2943 0.7887 0.1412 0.125 Uiso 1 1 calc R . .
H9C H 0.4867 0.8144 0.1157 0.125 Uiso 1 1 calc R . .
C8 C 0.3743(10) 0.9439(3) 0.0549(2) 0.083(2) Uani 1 1 d . . .
H8A H 0.3540 0.9224 0.0190 0.124 Uiso 1 1 calc R . .
H8B H 0.5081 0.9462 0.0625 0.124 Uiso 1 1 calc R . .
H8C H 0.3227 0.9887 0.0538 0.124 Uiso 1 1 calc R . .
C7 C 0.0099(10) 0.8925(4) 0.0979(3) 0.111(3) Uani 1 1 d . . .
H7A H -0.0158 0.8666 0.0644 0.166 Uiso 1 1 calc R . .
H7B H -0.0401 0.9372 0.0933 0.166 Uiso 1 1 calc R . .
H7C H -0.0490 0.8714 0.1299 0.166 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
C11 C12 1.200(7) . ?
C11 C10 1.427(7) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
O1 C1 1.231(5) . ?
N1 O3 1.219(6) . ?
N1 O2 1.222(5) . ?
N1 C2 1.470(6) . ?
C2 C3 1.369(6) . ?
C2 C1 1.464(6) . ?
C5 C6 1.366(6) . ?
C5 C4 1.394(7) . ?
C5 H5 0.9300 . ?
C6 N3 1.460(6) . ?
C6 C1 1.469(6) . ?
N3 O7 1.211(6) . ?
N3 O6 1.232(6) . ?
C4 C3 1.401(6) . ?
C4 N2 1.440(6) . ?
C3 H3 0.9300 . ?
N2 O4 1.231(6) . ?
N2 O5 1.238(6) . ?
P1 C8 1.774(6) . ?
P1 C7 1.783(7) . ?
P1 C9 1.786(6) . ?
P1 C10 1.805(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C10 145.4(13) . . ?
C12 C11 H11 107.3 . . ?
C10 C11 H11 107.3 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
O3 N1 O2 121.8(5) . . ?
O3 N1 C2 118.8(5) . . ?
O2 N1 C2 119.4(4) . . ?
C3 C2 C1 124.5(4) . . ?
C3 C2 N1 116.1(4) . . ?
C1 C2 N1 119.4(4) . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 N3 116.9(4) . . ?
C5 C6 C1 124.7(4) . . ?
N3 C6 C1 118.3(4) . . ?
O7 N3 O6 123.6(5) . . ?
O7 N3 C6 119.6(5) . . ?
O6 N3 C6 116.8(5) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 N2 119.9(5) . . ?
C3 C4 N2 119.7(5) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O1 C1 C2 125.0(4) . . ?
O1 C1 C6 123.9(4) . . ?
C2 C1 C6 111.1(4) . . ?
O4 N2 O5 122.3(5) . . ?
O4 N2 C4 118.9(5) . . ?
O5 N2 C4 118.8(5) . . ?
C8 P1 C7 111.6(4) . . ?
C8 P1 C9 110.0(3) . . ?
C7 P1 C9 108.3(4) . . ?
C8 P1 C10 109.7(3) . . ?
C7 P1 C10 108.2(3) . . ?
C9 P1 C10 109.0(3) . . ?
C11 C10 P1 111.6(5) . . ?
C11 C10 H10A 109.3 . . ?
P1 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
P1 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
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 . . ?
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 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 . . ?

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
O3 N1 C2 C3 -17.9(6) . . . . ?
O2 N1 C2 C3 161.5(5) . . . . ?
O3 N1 C2 C1 161.3(5) . . . . ?
O2 N1 C2 C1 -19.3(6) . . . . ?
C4 C5 C6 N3 -179.0(4) . . . . ?
C4 C5 C6 C1 2.3(7) . . . . ?
C5 C6 N3 O7 148.6(5) . . . . ?
C1 C6 N3 O7 -32.6(7) . . . . ?
C5 C6 N3 O6 -28.7(7) . . . . ?
C1 C6 N3 O6 150.0(5) . . . . ?
C6 C5 C4 C3 -1.6(7) . . . . ?
C6 C5 C4 N2 179.6(4) . . . . ?
C1 C2 C3 C4 2.0(7) . . . . ?
N1 C2 C3 C4 -178.8(4) . . . . ?
C5 C4 C3 C2 -0.5(7) . . . . ?
N2 C4 C3 C2 178.3(4) . . . . ?
C3 C2 C1 O1 178.9(5) . . . . ?
N1 C2 C1 O1 -0.3(7) . . . . ?
C3 C2 C1 C6 -1.3(6) . . . . ?
N1 C2 C1 C6 179.6(4) . . . . ?
C5 C6 C1 O1 178.9(5) . . . . ?
N3 C6 C1 O1 0.2(7) . . . . ?
C5 C6 C1 C2 -0.9(6) . . . . ?
N3 C6 C1 C2 -179.6(4) . . . . ?
C5 C4 N2 O4 -178.2(5) . . . . ?
C3 C4 N2 O4 3.0(7) . . . . ?
C5 C4 N2 O5 2.8(7) . . . . ?
C3 C4 N2 O5 -176.0(5) . . . . ?
C12 C11 C10 P1 120.2(14) . . . . ?
C8 P1 C10 C11 -65.5(8) . . . . ?
C7 P1 C10 C11 172.6(7) . . . . ?
C9 P1 C10 C11 55.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_293K
_database_code_depnum_ccdc_archive 'CCDC 1866564'
_audit_update_record             
;
2018-09-08 deposited with the CCDC.
2018-10-26 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 O P'
_chemical_formula_sum            'C11 H16 N3 O8 P'
_chemical_formula_weight         349.24

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/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                   6.8885(14)
_cell_length_b                   19.726(4)
_cell_length_c                   12.287(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.24(3)
_cell_angle_gamma                90.00
_cell_volume                     1594.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1997
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15454
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3635
_reflns_number_gt                1997
_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)+(0.0688P)²+0.6047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3635
_refine_ls_number_parameters     212
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.1002
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1755
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.140
_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
O3 O 0.9106(8) 1.13184(19) 0.6770(4) 0.1351(18) Uani 1 1 d U . .
O2 O 1.0020(9) 1.0525(2) 0.7825(3) 0.160(2) Uani 1 1 d U . .
O7 O 0.9436(6) 0.81848(17) 0.5621(4) 0.1002(12) Uani 1 1 d . . .
O6 O 0.6322(6) 0.81298(17) 0.4583(3) 0.1013(13) Uani 1 1 d . . .
O5 O 0.4753(6) 1.0129(2) 0.2113(3) 0.0986(12) Uani 1 1 d . . .
O4 O 0.5381(5) 1.1109(2) 0.2894(3) 0.0904(11) Uani 1 1 d . . .
N1 N 0.9201(6) 1.07282(19) 0.6917(3) 0.0636(10) Uani 1 1 d U . .
N3 N 0.7844(7) 0.84488(19) 0.5100(3) 0.0679(10) Uani 1 1 d . . .
N2 N 0.5493(5) 1.0491(2) 0.2937(3) 0.0686(10) Uani 1 1 d . . .
C2 C 0.8379(5) 1.02745(19) 0.5974(3) 0.0430(9) Uani 1 1 d . . .
C1 C 0.8629(6) 0.9545(2) 0.6142(4) 0.0473(9) Uani 1 1 d . . .
C6 C 0.7707(6) 0.91852(19) 0.5088(3) 0.0485(10) Uani 1 1 d . . .
C5 C 0.6679(5) 0.9477(2) 0.4079(3) 0.0501(10) Uani 1 1 d . . .
H5 H 0.6074 0.9211 0.3445 0.060 Uiso 1 1 calc R . .
C4 C 0.6548(5) 1.0175(2) 0.4010(3) 0.0486(10) Uani 1 1 d . . .
C3 C 0.7397(5) 1.0570(2) 0.4946(3) 0.0491(10) Uani 1 1 d . . .
H3 H 0.7308 1.1040 0.4886 0.059 Uiso 1 1 calc R . .
P1 P 0.15151(18) 0.64868(5) 0.46710(9) 0.0569(4) Uani 1 1 d . . .
O8 O 0.4927(6) 0.6821(2) 0.6094(4) 0.1148(14) Uani 1 1 d . . .
C7 C -0.1098(7) 0.6455(2) 0.4554(4) 0.0816(14) Uani 1 1 d . . .
H7A H -0.1815 0.6226 0.3863 0.122 Uiso 1 1 calc R . .
H7B H -0.1615 0.6908 0.4543 0.122 Uiso 1 1 calc R . .
H7C H -0.1287 0.6214 0.5195 0.122 Uiso 1 1 calc R . .
C9 C 0.2507(7) 0.5658(2) 0.4678(4) 0.0811(15) Uani 1 1 d . . .
H9A H 0.2289 0.5404 0.5298 0.122 Uiso 1 1 calc R . .
H9B H 0.3938 0.5683 0.4767 0.122 Uiso 1 1 calc R . .
H9C H 0.1832 0.5436 0.3971 0.122 Uiso 1 1 calc R . .
C8 C 0.1934(8) 0.6982(2) 0.3555(4) 0.0862(16) Uani 1 1 d . . .
H8A H 0.1256 0.6777 0.2834 0.129 Uiso 1 1 calc R . .
H8B H 0.3366 0.7008 0.3647 0.129 Uiso 1 1 calc R . .
H8C H 0.1408 0.7431 0.3579 0.129 Uiso 1 1 calc R . .
C10 C 0.2844(7) 0.6893(3) 0.5994(4) 0.0790(15) Uani 1 1 d . . .
H10A H 0.2474 0.7368 0.5979 0.095 Uiso 1 1 calc R . .
H10B H 0.2525 0.6676 0.6628 0.095 Uiso 1 1 calc R . .
C11 C 0.6202(8) 0.7226(3) 0.6895(4) 0.0963(17) Uani 1 1 d . . .
H11A H 0.5848 0.7693 0.6721 0.144 Uiso 1 1 calc R . .
H11B H 0.7578 0.7151 0.6894 0.144 Uiso 1 1 calc R . .
H11C H 0.6075 0.7119 0.7633 0.144 Uiso 1 1 calc R . .
O1 O 0.9470(5) 0.92626(14) 0.7060(2) 0.0714(9) 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
O3 N1 1.177(4) . ?
O2 N1 1.162(4) . ?
O7 N3 1.212(5) . ?
O6 N3 1.226(5) . ?
O5 N2 1.220(5) . ?
O4 N2 1.222(5) . ?
N1 C2 1.441(5) . ?
N3 C6 1.456(5) . ?
N2 C4 1.444(5) . ?
C2 C3 1.373(5) . ?
C2 C1 1.456(5) . ?
C1 O1 1.237(4) . ?
C1 C6 1.449(5) . ?
C6 C5 1.360(5) . ?
C5 C4 1.380(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.369(5) . ?
C3 H3 0.9300 . ?
P1 C7 1.764(5) . ?
P1 C9 1.771(4) . ?
P1 C8 1.776(5) . ?
P1 C10 1.800(4) . ?
O8 C11 1.366(6) . ?
O8 C10 1.410(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O3 118.6(4) . . ?
O2 N1 C2 121.4(4) . . ?
O3 N1 C2 120.0(4) . . ?
O7 N3 O6 123.7(4) . . ?
O7 N3 C6 118.7(4) . . ?
O6 N3 C6 117.7(4) . . ?
O5 N2 O4 122.8(4) . . ?
O5 N2 C4 118.6(4) . . ?
O4 N2 C4 118.5(4) . . ?
C3 C2 N1 116.4(4) . . ?
C3 C2 C1 123.7(4) . . ?
N1 C2 C1 119.8(4) . . ?
O1 C1 C6 123.8(4) . . ?
O1 C1 C2 125.4(4) . . ?
C6 C1 C2 110.8(4) . . ?
C5 C6 C1 125.4(4) . . ?
C5 C6 N3 116.5(4) . . ?
C1 C6 N3 118.1(4) . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 N2 119.8(4) . . ?
C5 C4 N2 119.5(4) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C7 P1 C9 110.5(2) . . ?
C7 P1 C8 110.6(3) . . ?
C9 P1 C8 111.2(2) . . ?
C7 P1 C10 108.8(2) . . ?
C9 P1 C10 108.3(2) . . ?
C8 P1 C10 107.3(2) . . ?
C11 O8 C10 115.1(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 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 . . ?
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 . . ?
O8 C10 P1 105.4(3) . . ?
O8 C10 H10A 110.7 . . ?
P1 C10 H10A 110.7 . . ?
O8 C10 H10B 110.7 . . ?
P1 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
O8 C11 H11A 109.5 . . ?
O8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C3 178.3(5) . . . . ?
O3 N1 C2 C3 -4.0(6) . . . . ?
O2 N1 C2 C1 -2.1(6) . . . . ?
O3 N1 C2 C1 175.6(4) . . . . ?
C3 C2 C1 O1 -178.5(4) . . . . ?
N1 C2 C1 O1 1.9(6) . . . . ?
C3 C2 C1 C6 0.0(5) . . . . ?
N1 C2 C1 C6 -179.6(3) . . . . ?
O1 C1 C6 C5 176.4(4) . . . . ?
C2 C1 C6 C5 -2.2(5) . . . . ?
O1 C1 C6 N3 -2.3(6) . . . . ?
C2 C1 C6 N3 179.1(3) . . . . ?
O7 N3 C6 C5 139.2(4) . . . . ?
O6 N3 C6 C5 -41.3(5) . . . . ?
O7 N3 C6 C1 -42.0(6) . . . . ?
O6 N3 C6 C1 137.6(4) . . . . ?
C1 C6 C5 C4 3.0(6) . . . . ?
N3 C6 C5 C4 -178.3(4) . . . . ?
C6 C5 C4 C3 -1.4(6) . . . . ?
C6 C5 C4 N2 178.8(3) . . . . ?
O5 N2 C4 C3 179.8(4) . . . . ?
O4 N2 C4 C3 -0.2(6) . . . . ?
O5 N2 C4 C5 -0.5(6) . . . . ?
O4 N2 C4 C5 179.5(4) . . . . ?
C5 C4 C3 C2 -0.6(6) . . . . ?
N2 C4 C3 C2 179.1(3) . . . . ?
N1 C2 C3 C4 -179.1(3) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
C11 O8 C10 P1 165.3(4) . . . . ?
C7 P1 C10 O8 172.7(3) . . . . ?
C9 P1 C10 O8 52.5(4) . . . . ?
C8 P1 C10 O8 -67.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_5_353K
_database_code_depnum_ccdc_archive 'CCDC 1866566'
_audit_update_record             
;
2018-09-08 deposited with the CCDC.
2018-10-26 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 O P'
_chemical_formula_sum            'C11 H16 N3 O8 P'
_chemical_formula_weight         349.24

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           orthorhombic
_symmetry_space_group_name_H-M   'C m c m'
_symmetry_space_group_name_HALL  '-C 2c 2'

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

_cell_length_a                   11.5686(15)
_cell_length_b                   20.037(3)
_cell_length_c                   7.0578(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1636.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    353(2)
_cell_measurement_reflns_used    394
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      24.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9630
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      353(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  'XtaLAB Synergy R, DW system, HyPix'
_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            3251
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         24.98
_reflns_number_total             799
_reflns_number_gt                394
_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)+(0.0020P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         799
_refine_ls_number_parameters     57
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.1223
_refine_ls_wR_factor_ref         0.3895
_refine_ls_wR_factor_gt          0.3421
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.154
_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 0.5000 1.14257(17) 0.2500 0.59(3) Uani 1 4 d SD . .
N2 N 0.5000 0.85559(17) 0.2500 0.50(3) Uani 1 4 d SD . .
N1 N 0.2865(2) 1.06876(15) 0.2500 0.234(6) Uani 1 2 d SD . .
C3 C 0.3957(3) 0.96289(12) 0.2500 0.234(6) Uani 1 2 d SD . .
H3A H 0.3237 0.9392 0.2500 0.281 Uiso 1 2 d SR . .
C4 C 0.5000 0.92614(13) 0.2500 0.234(6) Uani 1 4 d SD . .
C2 C 0.3940(3) 1.03423(13) 0.2500 0.234(6) Uani 1 2 d SD . .
C1 C 0.5000 1.07056(13) 0.2500 0.234(6) Uani 1 4 d SD . .
P1 P 0.0000 0.16684(14) 0.7500 0.263(5) Uani 1 4 d SD . .
O2 O 0.2772(12) 1.1268(2) 0.2500 0.400(12) Uani 1 2 d SD . .
O4 O 0.5878(13) 0.8288(10) 0.2500 0.59(2) Uani 1 2 d SD . .
O3 O 0.1945(4) 1.0440(5) 0.2500 0.511(13) Uani 1 2 d SD . .
C5 C 0.13031(16) 0.21224(15) 0.7500 0.633(15) Uani 1 2 d SD . .
H5A H 0.1151 0.2593 0.7500 0.760 Uiso 1 2 d SR . .
H5B H 0.1738 0.2007 0.8611 0.760 Uiso 1 1 d R . .
C6 C 0.0000 0.10477(16) 0.9583(3) 1.15(5) Uani 1 2 d SD . .
H6A H -0.0690 0.1041 1.0337 1.379 Uiso 0.50 1 d PR . .
H6B H 0.0690 0.1041 1.0337 1.379 Uiso 0.50 1 d PR . .
C7 C 0.0000 0.04901(17) 0.7500 0.633(15) Uani 1 4 d SD . .
O5 O 0.0000 -0.0231(4) 0.7500 0.633(15) Uani 1 4 d SD . .
H5C H 0.0601 -0.0475 0.7500 0.633 Uiso 0.50 2 d SPR . .


_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 1.443(4) . ?
N2 O4 1.149(16) 11_655 ?
N2 O4 1.149(17) . ?
N2 C4 1.414(4) . ?
N1 O2 1.168(5) . ?
N1 O3 1.173(6) . ?
N1 C2 1.424(4) . ?
C3 C4 1.413(3) . ?
C3 C2 1.430(3) . ?
C3 H3A 0.9600 . ?
C4 C3 1.413(3) 11_655 ?
C2 C1 1.426(3) . ?
C1 C2 1.426(3) 11_655 ?
P1 C5 1.761(2) . ?
P1 C5 1.761(2) 11 ?
P1 C6 1.926(3) 10_557 ?
P1 C6 1.926(3) . ?
P1 C7 2.361(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C6 C7 1.847(3) . ?
C6 H6A 0.9599 . ?
C6 H6B 0.9599 . ?
C7 O5 1.445(8) . ?
C7 C6 1.847(3) 10_557 ?
O5 H5C 0.8499 . ?

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
O4 N2 O4 124.3(19) 11_655 . ?
O4 N2 C4 117.8(9) 11_655 . ?
O4 N2 C4 117.8(9) . . ?
O2 N1 O3 109.7(9) . . ?
O2 N1 C2 124.3(7) . . ?
O3 N1 C2 125.9(5) . . ?
C4 C3 C2 122.2(3) . . ?
C4 C3 H3A 118.9 . . ?
C2 C3 H3A 118.9 . . ?
N2 C4 C3 121.41(15) . 11_655 ?
N2 C4 C3 121.41(15) . . ?
C3 C4 C3 117.2(3) 11_655 . ?
N1 C2 C1 120.2(2) . . ?
N1 C2 C3 119.9(3) . . ?
C1 C2 C3 119.9(3) . . ?
C2 C1 C2 118.6(3) . 11_655 ?
C2 C1 O1 120.70(14) . . ?
C2 C1 O1 120.70(14) 11_655 . ?
C5 P1 C5 117.8(2) . 11 ?
C5 P1 C6 109.49(6) . 10_557 ?
C5 P1 C6 109.49(6) 11 10_557 ?
C5 P1 C6 109.49(6) . . ?
C5 P1 C6 109.49(6) 11 . ?
C6 P1 C6 99.5(2) 10_557 . ?
C5 P1 C7 121.10(12) . . ?
C5 P1 C7 121.10(12) 11 . ?
C6 P1 C7 49.77(11) 10_557 . ?
C6 P1 C7 49.77(11) . . ?
P1 C5 H5A 110.5 . . ?
P1 C5 H5B 108.9 . . ?
H5A C5 H5B 109.5 . . ?
C7 C6 P1 77.47(12) . . ?
C7 C6 H6A 115.6 . . ?
P1 C6 H6A 115.6 . . ?
C7 C6 H6B 115.6 . . ?
P1 C6 H6B 115.6 . . ?
H6A C6 H6B 112.6 . . ?
O5 C7 C6 127.24(12) . . ?
O5 C7 C6 127.24(12) . 10_557 ?
C6 C7 C6 105.5(2) . 10_557 ?
O5 C7 P1 180.0 . . ?
C6 C7 P1 52.76(12) . . ?
C6 C7 P1 52.76(12) 10_557 . ?
C7 O5 H5C 125.1 . . ?

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
O4 N2 C4 C3 180.0 11_655 . . 11_655 ?
O4 N2 C4 C3 0.0 . . . 11_655 ?
O4 N2 C4 C3 0.0 11_655 . . . ?
O4 N2 C4 C3 180.0 . . . . ?
C2 C3 C4 N2 180.0 . . . . ?
C2 C3 C4 C3 0.0 . . . 11_655 ?
O2 N1 C2 C1 0.0 . . . . ?
O3 N1 C2 C1 180.0 . . . . ?
O2 N1 C2 C3 180.0 . . . . ?
O3 N1 C2 C3 0.0 . . . . ?
C4 C3 C2 N1 180.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
N1 C2 C1 C2 180.0 . . . 11_655 ?
C3 C2 C1 C2 0.0 . . . 11_655 ?
N1 C2 C1 O1 0.0 . . . . ?
C3 C2 C1 O1 180.0 . . . . ?
C5 P1 C6 C7 -114.73(12) . . . . ?
C5 P1 C6 C7 114.73(12) 11 . . . ?
C6 P1 C6 C7 0.0 10_557 . . . ?
P1 C6 C7 O5 180.0 . . . . ?
P1 C6 C7 C6 0.0 . . . 10_557 ?
C5 P1 C7 O5 0(100) . . . . ?
C5 P1 C7 O5 0(100) 11 . . . ?
C6 P1 C7 O5 0(100) 10_557 . . . ?
C6 P1 C7 O5 0(100) . . . . ?
C5 P1 C7 C6 90.0 . . . . ?
C5 P1 C7 C6 -90.0 11 . . . ?
C6 P1 C7 C6 180.0 10_557 . . . ?
C5 P1 C7 C6 -90.0 . . . 10_557 ?
C5 P1 C7 C6 90.0 11 . . 10_557 ?
C6 P1 C7 C6 180.0 . . . 10_557 ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.673
_refine_diff_density_rms         0.134
# start Validation Reply Form
_vrf_PLAT242_5_353K              
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C1 Check 
RESPONSE: The terminal O atom bonded to this atom has relatively high atomic
displacement parameter.
;
_vrf_PLAT084_5_353K              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.39 Report
RESPONSE: As the measured temperature is high, the intense thermal vibrations 
of all atoms cause the weak diffraction.
;
_vrf_PLAT241_5_353K              
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         N2 Check 
RESPONSE: The motion of nitrogroup is more intense than the benzene ring. 
Thus the C4 atom bonded to N2 has relatively low atomic displacement parameter.
;
# 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_5_293K
_database_code_depnum_ccdc_archive 'CCDC 1866565'
_audit_update_record             
;
2018-10-22 deposited with the CCDC.
2018-10-26 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 O P'
_chemical_formula_sum            'C11 H16 N3 O8 P'
_chemical_formula_weight         349.24

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           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'

_cell_length_a                   10.232(2)
_cell_length_b                   9.883(2)
_cell_length_c                   8.5961(17)
_cell_angle_alpha                102.92(3)
_cell_angle_beta                 99.20(3)
_cell_angle_gamma                68.34(3)
_cell_volume                     784.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3313
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5491
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5006
_reflns_number_gt                3313
_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)+(0.1231P)²+0.1177P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_number_reflns         5006
_refine_ls_number_parameters     423
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0769
_refine_ls_wR_factor_ref         0.2254
_refine_ls_wR_factor_gt          0.1921
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.004
_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
C1 C 0.6408(6) -0.0875(6) 0.8120(8) 0.0427(16) Uani 1 1 d . . .
C2 C 0.4993(7) -0.0017(6) 0.7535(8) 0.0437(17) Uani 1 1 d . . .
C3 C 0.4280(7) 0.1427(7) 0.8207(8) 0.0491(18) Uani 1 1 d . . .
H3 H 0.3356 0.1916 0.7835 0.059 Uiso 1 1 calc R . .
C4 C 0.5000(7) 0.2159(6) 0.9498(7) 0.0427(17) Uani 1 1 d . . .
C5 C 0.6366(6) 0.1400(7) 1.0124(8) 0.0503(18) Uani 1 1 d . . .
H5 H 0.6821 0.1858 1.0985 0.060 Uiso 1 1 calc R . .
C6 C 0.7016(6) -0.0074(6) 0.9402(8) 0.0461(18) Uani 1 1 d . . .
C18 C 0.2056(7) 0.7582(7) 0.2658(9) 0.0562(18) Uani 1 1 d . . .
H18A H 0.2819 0.6920 0.2037 0.084 Uiso 1 1 calc R . .
H18B H 0.2367 0.8305 0.3405 0.084 Uiso 1 1 calc R . .
H18C H 0.1280 0.8072 0.1958 0.084 Uiso 1 1 calc R . .
C19 C 0.0569(6) 0.5512(7) 0.2454(7) 0.0455(18) Uani 1 1 d . . .
H19A H 0.1223 0.4597 0.1955 0.068 Uiso 1 1 calc R . .
H19B H 0.0008 0.6065 0.1645 0.068 Uiso 1 1 calc R . .
H19C H -0.0035 0.5309 0.3048 0.068 Uiso 1 1 calc R . .
C20 C 0.0383(7) 0.7762(8) 0.5245(9) 0.062(2) Uani 1 1 d . . .
H20A H -0.0503 0.8317 0.4744 0.092 Uiso 1 1 calc R . .
H20B H 0.0830 0.8429 0.5874 0.092 Uiso 1 1 calc R . .
H20C H 0.0222 0.7199 0.5925 0.092 Uiso 1 1 calc R . .
C21 C 0.3044(7) 0.5393(7) 0.4693(8) 0.052(2) Uani 1 1 d . . .
H21A H 0.3559 0.4630 0.3863 0.063 Uiso 1 1 calc R . .
H21B H 0.3625 0.5991 0.5162 0.063 Uiso 1 1 calc R . .
C22 C 0.2920(7) 0.4628(7) 0.5986(9) 0.0520(18) Uani 1 1 d . . .
H22A H 0.3849 0.3996 0.6341 0.062 Uiso 1 1 calc R . .
H22B H 0.2519 0.5362 0.6900 0.062 Uiso 1 1 calc R . .
C12 C 0.3648(8) 1.0684(7) 0.1942(7) 0.0488(19) Uani 1 1 d U . .
C13 C 0.5040(7) 0.9782(7) 0.2482(7) 0.0400(16) Uani 1 1 d U . .
C14 C 0.5717(6) 0.8343(6) 0.1881(7) 0.0354(15) Uani 1 1 d . . .
H14 H 0.6586 0.7819 0.2359 0.042 Uiso 1 1 calc R . .
C15 C 0.5112(7) 0.7680(6) 0.0579(8) 0.0427(17) Uani 1 1 d . . .
C16 C 0.3788(7) 0.8413(6) -0.0062(7) 0.0419(16) Uani 1 1 d . . .
H16 H 0.3383 0.7931 -0.0952 0.050 Uiso 1 1 calc R . .
C17 C 0.3077(7) 0.9802(7) 0.0570(8) 0.0448(18) Uani 1 1 d U . .
C7 C 0.8066(8) 0.2307(8) 0.7365(9) 0.057(2) Uani 1 1 d . . .
H7A H 0.7276 0.2055 0.6797 0.086 Uiso 1 1 calc R . .
H7B H 0.7806 0.2903 0.8390 0.086 Uiso 1 1 calc R . .
H7C H 0.8842 0.1418 0.7514 0.086 Uiso 1 1 calc R . .
C8 C 0.9671(8) 0.1998(8) 0.4794(10) 0.062(2) Uani 1 1 d . . .
H8A H 1.0430 0.1275 0.5296 0.093 Uiso 1 1 calc R . .
H8B H 1.0049 0.2522 0.4277 0.093 Uiso 1 1 calc R . .
H8C H 0.9131 0.1510 0.4012 0.093 Uiso 1 1 calc R . .
C9 C 0.9518(8) 0.4338(8) 0.7689(9) 0.061(2) Uani 1 1 d . . .
H9A H 0.8914 0.5005 0.8489 0.092 Uiso 1 1 calc R . .
H9B H 0.9815 0.4893 0.7121 0.092 Uiso 1 1 calc R . .
H9C H 1.0330 0.3672 0.8195 0.092 Uiso 1 1 calc R . .
C10 C 0.6967(6) 0.4467(6) 0.5354(8) 0.0411(17) Uani 1 1 d . . .
H10A H 0.6382 0.3883 0.4844 0.049 Uiso 1 1 calc R . .
H10B H 0.6449 0.5223 0.6186 0.049 Uiso 1 1 calc R . .
C11 C 0.7191(8) 0.5213(8) 0.4128(9) 0.061(2) Uani 1 1 d . . .
H11A H 0.7653 0.4454 0.3261 0.073 Uiso 1 1 calc R . .
H11B H 0.6275 0.5795 0.3684 0.073 Uiso 1 1 calc R . .
N1 N 0.4260(5) -0.0681(6) 0.6260(8) 0.0591(18) Uani 1 1 d U . .
N2 N 0.4228(6) 0.3641(5) 1.0231(6) 0.0452(15) Uani 1 1 d . . .
N3 N 0.8428(7) -0.0736(6) 1.0173(7) 0.068(2) Uani 1 1 d U . .
N4 N 0.5863(7) 1.0479(6) 0.3801(7) 0.0554(18) Uani 1 1 d . . .
N5 N 0.5831(8) 0.6164(7) -0.0186(8) 0.0624(19) Uani 1 1 d . . .
N6 N 0.1700(7) 1.0587(10) -0.0113(9) 0.090(3) Uani 1 1 d U . .
O1 O 0.7076(6) -0.2210(5) 0.7584(6) 0.0664(17) Uani 1 1 d . . .
O2 O 0.4490(8) -0.2001(6) 0.6036(8) 0.117(2) Uani 1 1 d . . .
O3 O 0.3184(8) 0.0010(8) 0.5684(11) 0.163(4) Uani 1 1 d U . .
O4 O 0.3026(6) 0.4248(5) 0.9697(6) 0.0691(18) Uani 1 1 d . . .
O5 O 0.4792(6) 0.4243(5) 1.1332(6) 0.0719(18) Uani 1 1 d . . .
O6 O 0.8528(6) -0.0612(7) 1.1598(8) 0.098(2) Uani 1 1 d . . .
O7 O 0.9226(8) -0.1697(10) 0.9458(11) 0.179(4) Uani 1 1 d U . .
O16 O 0.2017(5) 0.3738(5) 0.5347(6) 0.0631(15) Uani 1 1 d . . .
H16A H 0.2411 0.3049 0.4656 0.095 Uiso 1 1 calc R . .
O9 O 0.3040(7) 1.2001(6) 0.2507(7) 0.077(2) Uani 1 1 d . . .
O10 O 0.5449(8) 1.1754(7) 0.4194(11) 0.150(4) Uani 1 1 d . . .
O11 O 0.6694(6) 0.9680(5) 0.4673(6) 0.0637(14) Uani 1 1 d . . .
O12 O 0.7079(6) 0.5551(6) 0.0329(8) 0.0752(19) Uani 1 1 d . . .
O13 O 0.5196(6) 0.5593(6) -0.1369(6) 0.0724(16) Uani 1 1 d . . .
O14 O 0.1329(9) 1.0167(11) -0.1465(10) 0.193(5) Uani 1 1 d U . .
O15 O 0.0724(9) 1.1370(12) 0.0747(11) 0.158(4) Uani 1 1 d U . .
O8 O 0.7971(5) 0.6117(5) 0.4669(6) 0.0550(14) Uani 1 1 d . . .
H8 H 0.8386 0.5952 0.5543 0.083 Uiso 1 1 calc R . .
P2 P 0.14935(14) 0.65379(14) 0.37455(17) 0.0393(4) Uani 1 1 d . . .
P1 P 0.85533(15) 0.32795(15) 0.62817(18) 0.0413(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 1.259(7) . ?
C1 C6 1.408(9) . ?
C1 C2 1.456(8) . ?
C2 C3 1.379(8) . ?
C2 N1 1.404(8) . ?
C3 C4 1.440(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(8) . ?
C4 N2 1.434(7) . ?
C5 C6 1.401(8) . ?
C5 H5 0.9300 . ?
C6 N3 1.465(8) . ?
C18 P2 1.820(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 P2 1.739(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 P2 1.781(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.522(10) . ?
C21 P2 1.771(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O16 1.467(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C12 O9 1.238(8) . ?
C12 C13 1.441(9) . ?
C12 C17 1.480(9) . ?
C13 C14 1.352(8) . ?
C13 N4 1.497(9) . ?
C14 C15 1.347(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(9) . ?
C15 N5 1.455(8) . ?
C16 C17 1.328(8) . ?
C16 H16 0.9300 . ?
C17 N6 1.437(9) . ?
C7 P1 1.716(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 P1 1.795(8) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 P1 1.829(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.502(11) . ?
C10 P1 1.802(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O8 1.368(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N1 O3 1.161(8) . ?
N1 O2 1.212(7) . ?
N2 O5 1.187(7) . ?
N2 O4 1.218(7) . ?
N3 O7 1.129(10) . ?
N3 O6 1.195(8) . ?
N4 O10 1.159(8) . ?
N4 O11 1.215(7) . ?
N5 O12 1.250(8) . ?
N5 O13 1.255(8) . ?
N6 O14 1.195(10) . ?
N6 O15 1.246(10) . ?
O16 H16A 0.8200 . ?
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 C6 120.5(5) . . ?
O1 C1 C2 125.7(6) . . ?
C6 C1 C2 113.8(5) . . ?
C3 C2 N1 116.5(6) . . ?
C3 C2 C1 123.6(6) . . ?
N1 C2 C1 119.8(5) . . ?
C2 C3 C4 118.4(6) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 N2 120.8(5) . . ?
C5 C4 C3 121.0(5) . . ?
N2 C4 C3 117.9(5) . . ?
C6 C5 C4 117.4(6) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C1 125.7(5) . . ?
C5 C6 N3 111.8(5) . . ?
C1 C6 N3 122.5(5) . . ?
P2 C18 H18A 109.5 . . ?
P2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
P2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
P2 C19 H19A 109.5 . . ?
P2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
P2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
P2 C20 H20A 109.5 . . ?
P2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
P2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 P2 119.4(5) . . ?
C22 C21 H21A 107.5 . . ?
P2 C21 H21A 107.5 . . ?
C22 C21 H21B 107.5 . . ?
P2 C21 H21B 107.5 . . ?
H21A C21 H21B 107.0 . . ?
O16 C22 C21 109.6(6) . . ?
O16 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
O16 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O9 C12 C13 125.5(7) . . ?
O9 C12 C17 125.3(7) . . ?
C13 C12 C17 109.2(5) . . ?
C14 C13 C12 126.2(6) . . ?
C14 C13 N4 115.2(5) . . ?
C12 C13 N4 118.5(5) . . ?
C15 C14 C13 118.9(6) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 N5 121.4(6) . . ?
C16 C15 N5 117.8(6) . . ?
C17 C16 C15 120.9(6) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 N6 121.3(7) . . ?
C16 C17 C12 123.7(6) . . ?
N6 C17 C12 114.9(6) . . ?
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 115.3(5) . . ?
C11 C10 H10A 108.5 . . ?
P1 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
P1 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
O8 C11 C10 115.8(6) . . ?
O8 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
O8 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
O3 N1 O2 115.1(7) . . ?
O3 N1 C2 121.0(6) . . ?
O2 N1 C2 120.5(6) . . ?
O5 N2 O4 122.0(5) . . ?
O5 N2 C4 118.7(5) . . ?
O4 N2 C4 119.2(5) . . ?
O7 N3 O6 119.2(7) . . ?
O7 N3 C6 118.8(6) . . ?
O6 N3 C6 116.7(6) . . ?
O10 N4 O11 121.2(7) . . ?
O10 N4 C13 118.9(6) . . ?
O11 N4 C13 116.9(6) . . ?
O12 N5 O13 124.4(6) . . ?
O12 N5 C15 117.0(6) . . ?
O13 N5 C15 118.4(6) . . ?
O14 N6 O15 115.0(8) . . ?
O14 N6 C17 119.7(7) . . ?
O15 N6 C17 121.4(8) . . ?
C22 O16 H16A 109.5 . . ?
C11 O8 H8 109.5 . . ?
C19 P2 C21 111.9(3) . . ?
C19 P2 C20 108.7(3) . . ?
C21 P2 C20 108.7(3) . . ?
C19 P2 C18 110.8(3) . . ?
C21 P2 C18 106.5(3) . . ?
C20 P2 C18 110.2(4) . . ?
C7 P1 C8 108.9(4) . . ?
C7 P1 C10 107.7(3) . . ?
C8 P1 C10 110.7(3) . . ?
C7 P1 C9 107.1(4) . . ?
C8 P1 C9 110.3(4) . . ?
C10 P1 C9 111.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.1(7) . . . . ?
C6 C1 C2 C3 -2.6(10) . . . . ?
O1 C1 C2 N1 -0.1(11) . . . . ?
C6 C1 C2 N1 -179.9(6) . . . . ?
N1 C2 C3 C4 -178.9(6) . . . . ?
C1 C2 C3 C4 3.8(10) . . . . ?
C2 C3 C4 C5 -3.7(10) . . . . ?
C2 C3 C4 N2 -177.5(6) . . . . ?
N2 C4 C5 C6 176.1(7) . . . . ?
C3 C4 C5 C6 2.5(10) . . . . ?
C4 C5 C6 C1 -1.4(11) . . . . ?
C4 C5 C6 N3 -179.7(6) . . . . ?
O1 C1 C6 C5 -178.4(7) . . . . ?
C2 C1 C6 C5 1.4(10) . . . . ?
O1 C1 C6 N3 -0.3(11) . . . . ?
C2 C1 C6 N3 179.5(6) . . . . ?
P2 C21 C22 O16 55.9(6) . . . . ?
O9 C12 C13 C14 179.8(8) . . . . ?
C17 C12 C13 C14 -2.0(10) . . . . ?
O9 C12 C13 N4 -2.0(11) . . . . ?
C17 C12 C13 N4 176.2(6) . . . . ?
C12 C13 C14 C15 5.3(11) . . . . ?
N4 C13 C14 C15 -172.9(6) . . . . ?
C13 C14 C15 C16 -4.7(10) . . . . ?
C13 C14 C15 N5 175.9(6) . . . . ?
C14 C15 C16 C17 1.0(10) . . . . ?
N5 C15 C16 C17 -179.6(7) . . . . ?
C15 C16 C17 N6 178.8(7) . . . . ?
C15 C16 C17 C12 2.5(11) . . . . ?
O9 C12 C17 C16 176.2(8) . . . . ?
C13 C12 C17 C16 -2.0(10) . . . . ?
O9 C12 C17 N6 -0.3(12) . . . . ?
C13 C12 C17 N6 -178.5(6) . . . . ?
P1 C10 C11 O8 -59.9(7) . . . . ?
C3 C2 N1 O3 9.2(12) . . . . ?
C1 C2 N1 O3 -173.4(9) . . . . ?
C3 C2 N1 O2 -149.1(7) . . . . ?
C1 C2 N1 O2 28.4(10) . . . . ?
C5 C4 N2 O5 3.7(10) . . . . ?
C3 C4 N2 O5 177.5(6) . . . . ?
C5 C4 N2 O4 -177.2(7) . . . . ?
C3 C4 N2 O4 -3.4(9) . . . . ?
C5 C6 N3 O7 -155.2(10) . . . . ?
C1 C6 N3 O7 26.5(12) . . . . ?
C5 C6 N3 O6 50.7(9) . . . . ?
C1 C6 N3 O6 -127.7(8) . . . . ?
C14 C13 N4 O10 167.7(9) . . . . ?
C12 C13 N4 O10 -10.7(11) . . . . ?
C14 C13 N4 O11 -31.5(9) . . . . ?
C12 C13 N4 O11 150.1(7) . . . . ?
C14 C15 N5 O12 -6.3(10) . . . . ?
C16 C15 N5 O12 174.3(7) . . . . ?
C14 C15 N5 O13 178.0(6) . . . . ?
C16 C15 N5 O13 -1.4(10) . . . . ?
C16 C17 N6 O14 -19.7(14) . . . . ?
C12 C17 N6 O14 157.0(10) . . . . ?
C16 C17 N6 O15 136.9(10) . . . . ?
C12 C17 N6 O15 -46.5(13) . . . . ?
C22 C21 P2 C19 -72.1(6) . . . . ?
C22 C21 P2 C20 48.0(6) . . . . ?
C22 C21 P2 C18 166.7(5) . . . . ?
C11 C10 P1 C7 -169.9(5) . . . . ?
C11 C10 P1 C8 -50.9(6) . . . . ?
C11 C10 P1 C9 72.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.101

# start Validation Reply Form
_vrf_PLAT111_5_293K              
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Only non-centrosymmetric space groups have SHG effect??the 
compound is SHG-active at 293 K,thus it should have no centre of symmetry.
;
_vrf_PLAT113_5_293K              
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: Since the compound has SHG effect which can not exist in the 
centrosymmetric space groups like P-1, thus it is solved in the 
non-centrosymmetric space group P1.
;
# end Validation Reply Form
