# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1009538'
_audit_update_record             
;
2014-06-21 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'DNT derivative from PNP DNT synth'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H31 N15 O4 P2'
_chemical_formula_iupac          ?
_chemical_formula_weight         847.74

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.1121(11)
_cell_length_b                   12.5247(12)
_cell_length_c                   16.0476(16)
_cell_angle_alpha                70.424(2)
_cell_angle_beta                 72.600(2)
_cell_angle_gamma                83.653(2)
_cell_volume                     2007.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       blade/prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.220
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876

_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            48323
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             12028
_reflns_number_gt                7692
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1626
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_number_reflns         12028
_refine_ls_number_parameters     550
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0651P)²+1.6487P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.417
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XS 2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 1.09557(5) 0.26692(4) 0.28922(4) 0.01446(12) Uani d . . . 1 . .
P P2 0.90657(5) 0.23075(4) 0.19377(4) 0.01551(12) Uani d . . . 1 . .
N N15 1.00948(18) 0.23880(16) 0.23871(13) 0.0253(4) Uani d . . . 1 . .
C C5 1.0105(2) 0.29560(17) 0.39339(15) 0.0185(4) Uani d . . . 1 . .
C C6 1.0699(2) 0.2816(2) 0.46145(16) 0.0275(5) Uani d . . . 1 . .
H H6 1.1522 0.2492 0.4555 0.033 Uiso calc U . R 1 . .
C C7 1.0090(3) 0.3150(2) 0.53796(17) 0.0334(6) Uani d . . . 1 . .
H H7 1.0505 0.3074 0.5835 0.04 Uiso calc U . R 1 . .
C C8 0.8879(3) 0.3594(2) 0.54780(17) 0.0308(6) Uani d . . . 1 . .
H H8 0.8465 0.3822 0.6003 0.037 Uiso calc U . R 1 . .
C C9 0.8270(2) 0.37079(19) 0.48216(17) 0.0286(5) Uani d . . . 1 . .
H H9 0.743 0.3996 0.4901 0.034 Uiso calc U . R 1 . .
C C10 0.8883(2) 0.34021(18) 0.40428(16) 0.0227(5) Uani d . . . 1 . .
H H10 0.8468 0.3497 0.3583 0.027 Uiso calc U . R 1 . .
C C11 1.3270(2) 0.1594(2) 0.30077(18) 0.0296(5) Uani d . . . 1 . .
H H11 1.3645 0.2318 0.2689 0.036 Uiso calc U . R 1 . .
C C12 1.4015(3) 0.0644(2) 0.3275(2) 0.0402(7) Uani d . . . 1 . .
H H12 1.4901 0.072 0.3137 0.048 Uiso calc U . R 1 . .
C C13 1.3472(3) -0.0408(2) 0.37416(19) 0.0352(6) Uani d . . . 1 . .
H H13 1.3987 -0.1054 0.3919 0.042 Uiso calc U . R 1 . .
C C14 1.2189(3) -0.05272(19) 0.39500(17) 0.0287(5) Uani d . . . 1 . .
H H14 1.182 -0.1253 0.4274 0.034 Uiso calc U . R 1 . .
C C15 1.1432(2) 0.04121(18) 0.36871(16) 0.0229(5) Uani d . . . 1 . .
H H15 1.0547 0.033 0.3832 0.027 Uiso calc U . R 1 . .
C C16 1.1979(2) 0.14807(17) 0.32080(14) 0.0180(4) Uani d . . . 1 . .
C C17 1.2087(2) 0.4725(2) 0.25006(19) 0.0311(6) Uani d . . . 1 . .
H H17 1.1708 0.466 0.313 0.037 Uiso calc U . R 1 . .
C C18 1.2804(2) 0.5667(2) 0.1917(2) 0.0364(6) Uani d . . . 1 . .
H H18 1.2916 0.6245 0.2148 0.044 Uiso calc U . R 1 . .
C C19 1.3347(3) 0.5763(2) 0.1016(2) 0.0425(8) Uani d . . . 1 . .
H H19 1.3824 0.6415 0.0615 0.051 Uiso calc U . R 1 . .
C C20 1.3206(4) 0.4917(3) 0.0684(2) 0.0658(12) Uani d . . . 1 . .
H H20 1.3605 0.4979 0.0057 0.079 Uiso calc U . R 1 . .
C C21 1.2483(3) 0.3971(3) 0.12609(18) 0.0472(8) Uani d . . . 1 . .
H H21 1.2378 0.3393 0.1029 0.057 Uiso calc U . R 1 . .
C C22 1.1922(2) 0.38809(17) 0.21693(15) 0.0178(4) Uani d . . . 1 . .
C C23 0.8098(2) 0.10924(17) 0.26267(16) 0.0196(4) Uani d . . . 1 . .
C C24 0.7624(2) 0.04720(18) 0.22188(17) 0.0233(5) Uani d . . . 1 . .
H H24 0.7733 0.0735 0.1573 0.028 Uiso calc U . R 1 . .
C C25 0.6989(2) -0.05332(19) 0.27626(19) 0.0297(6) Uani d . . . 1 . .
H H25 0.6654 -0.0956 0.2491 0.036 Uiso calc U . R 1 . .
C C26 0.6847(2) -0.0914(2) 0.37001(19) 0.0325(6) Uani d . . . 1 . .
H H26 0.6442 -0.1615 0.4067 0.039 Uiso calc U . R 1 . .
C C27 0.7282(3) -0.0295(2) 0.41079(18) 0.0340(6) Uani d . . . 1 . .
H H27 0.715 -0.0554 0.4756 0.041 Uiso calc U . R 1 . .
C C28 0.7918(2) 0.0716(2) 0.35704(17) 0.0269(5) Uani d . . . 1 . .
H H28 0.8227 0.1143 0.3851 0.032 Uiso calc U . R 1 . .
C C29 1.0913(2) 0.15366(17) 0.06798(15) 0.0206(4) Uani d . . . 1 . .
H H29 1.1374 0.134 0.1124 0.025 Uiso calc U . R 1 . .
C C30 1.1388(2) 0.12568(18) -0.01275(16) 0.0248(5) Uani d . . . 1 . .
H H30 1.2177 0.0872 -0.0236 0.03 Uiso calc U . R 1 . .
C C31 1.0718(2) 0.1535(2) -0.07716(17) 0.0282(5) Uani d . . . 1 . .
H H31 1.1036 0.1324 -0.1314 0.034 Uiso calc U . R 1 . .
C C32 0.9582(2) 0.2122(2) -0.06293(17) 0.0296(5) Uani d . . . 1 . .
H H32 0.9132 0.2325 -0.108 0.035 Uiso calc U . R 1 . .
C C33 0.9102(2) 0.2414(2) 0.01690(16) 0.0253(5) Uani d . . . 1 . .
H H33 0.8326 0.2822 0.0264 0.03 Uiso calc U . R 1 . .
C C34 0.9762(2) 0.21056(17) 0.08342(15) 0.0188(4) Uani d . . . 1 . .
C C35 0.8073(2) 0.35489(17) 0.17528(14) 0.0180(4) Uani d . . . 1 . .
C C36 0.6037(3) 0.4466(2) 0.18575(17) 0.0317(6) Uani d . . . 1 . .
H H36 0.5143 0.4424 0.2055 0.038 Uiso calc U . R 1 . .
C C37 0.6621(3) 0.5506(2) 0.13853(17) 0.0329(6) Uani d . . . 1 . .
H H37 0.6123 0.6176 0.1253 0.04 Uiso calc U . R 1 . .
C C38 0.6765(2) 0.34869(19) 0.20398(16) 0.0237(5) Uani d . . . 1 . .
H H38 0.6368 0.2773 0.2361 0.028 Uiso calc U . R 1 . .
C C39 0.7912(3) 0.55774(19) 0.11079(17) 0.0314(6) Uani d . . . 1 . .
H H39 0.8301 0.6296 0.0791 0.038 Uiso calc U . R 1 . .
C C40 0.8655(2) 0.46049(18) 0.12879(16) 0.0251(5) Uani d . . . 1 . .
H H40 0.9548 0.4656 0.1098 0.03 Uiso calc U . R 1 . .
O O1 0.5121(2) 0.31599(16) 0.49138(15) 0.0480(6) Uani d . . . 1 . .
O O2 0.3297(2) 0.3695(2) 0.46664(17) 0.0584(7) Uani d . . . 1 . .
N N1 0.4417(2) 0.38496(19) 0.45384(16) 0.0366(5) Uani d . . . 1 . .
N N2 0.4245(2) 0.57188(18) 0.35076(14) 0.0294(5) Uani d . . . 1 . .
N N3 0.5092(2) 0.65644(17) 0.30064(14) 0.0284(5) Uani d . . . 1 . .
H H1 0.4888 0.7237 0.2638 0.034 Uiso d U P R 0.5 . .
N N4 0.7243(2) 0.68974(17) 0.27086(15) 0.0304(5) Uani d . . . 1 . .
N N5 0.8260(2) 0.64435(17) 0.28313(14) 0.0301(5) Uani d . . . 1 . .
N N6 0.9244(2) 0.6157(2) 0.28641(18) 0.0430(6) Uani d . . . 1 . .
N N7 0.61686(19) 0.51523(16) 0.37500(13) 0.0254(4) Uani d . . . 1 . .
C C1 0.4949(2) 0.4931(2) 0.39243(16) 0.0261(5) Uani d . . . 1 . .
C C2 0.6199(2) 0.61936(19) 0.31652(16) 0.0244(5) Uani d . . . 1 . .
O O3 0.4301(2) 1.20555(16) 0.02864(15) 0.0488(6) Uani d . . . 1 . .
O O4 0.6196(2) 1.13758(18) 0.02235(17) 0.0573(6) Uani d . . . 1 . .
N N8 0.5049(2) 1.12851(19) 0.04917(16) 0.0364(5) Uani d . . . 1 . .
N N9 0.5284(2) 0.93336(18) 0.13478(15) 0.0316(5) Uani d . . . 1 . .
N N10 0.4449(2) 0.84889(17) 0.18828(14) 0.0288(5) Uani d . . . 1 . .
H H3 0.4651 0.7853 0.2271 0.035 Uiso d U P R 0.5 . .
N N11 0.2258(2) 0.82136(17) 0.23875(15) 0.0311(5) Uani d . . . 1 . .
N N12 0.1216(2) 0.87044(17) 0.24167(15) 0.0300(5) Uani d . . . 1 . .
N N13 0.0211(2) 0.9024(2) 0.25172(18) 0.0423(6) Uani d . . . 1 . .
N N14 0.3286(2) 1.00026(16) 0.13843(14) 0.0259(4) Uani d . . . 1 . .
C C3 0.4534(2) 1.0182(2) 0.10812(17) 0.0275(5) Uani d . . . 1 . .
C C4 0.3300(2) 0.89180(19) 0.18848(16) 0.0249(5) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 N15 . 1.5575(19) ?
P1 C5 . 1.789(2) ?
P1 C16 . 1.797(2) ?
P1 C22 . 1.799(2) ?
P2 N15 . 1.5510(19) ?
P2 C23 . 1.794(2) ?
P2 C35 . 1.797(2) ?
P2 C34 . 1.799(2) ?
C5 C6 . 1.392(3) ?
C5 C10 . 1.394(3) ?
C6 C7 . 1.387(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.382(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.376(4) ?
C8 H8 . 0.95 ?
C9 C10 . 1.388(3) ?
C9 H9 . 0.95 ?
C10 H10 . 0.95 ?
C11 C16 . 1.386(3) ?
C11 C12 . 1.392(3) ?
C11 H11 . 0.95 ?
C12 C13 . 1.381(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.377(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.389(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.401(3) ?
C15 H15 . 0.95 ?
C17 C22 . 1.383(3) ?
C17 C18 . 1.387(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.359(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.377(5) ?
C19 H19 . 0.95 ?
C20 C21 . 1.392(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.374(3) ?
C21 H21 . 0.95 ?
C23 C28 . 1.385(3) ?
C23 C24 . 1.396(3) ?
C24 C25 . 1.391(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.382(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.368(4) ?
C26 H26 . 0.95 ?
C27 C28 . 1.396(3) ?
C27 H27 . 0.95 ?
C28 H28 . 0.95 ?
C29 C34 . 1.391(3) ?
C29 C30 . 1.391(3) ?
C29 H29 . 0.95 ?
C30 C31 . 1.381(3) ?
C30 H30 . 0.95 ?
C31 C32 . 1.385(3) ?
C31 H31 . 0.95 ?
C32 C33 . 1.386(3) ?
C32 H32 . 0.95 ?
C33 C34 . 1.399(3) ?
C33 H33 . 0.95 ?
C35 C38 . 1.390(3) ?
C35 C40 . 1.401(3) ?
C36 C37 . 1.387(4) ?
C36 C38 . 1.387(3) ?
C36 H36 . 0.95 ?
C37 C39 . 1.373(4) ?
C37 H37 . 0.95 ?
C38 H38 . 0.95 ?
C39 C40 . 1.390(3) ?
C39 H39 . 0.95 ?
C40 H40 . 0.95 ?
O1 N1 . 1.226(3) ?
O2 N1 . 1.226(3) ?
N1 C1 . 1.445(3) ?
N2 C1 . 1.316(3) ?
N2 N3 . 1.361(3) ?
N3 C2 . 1.332(3) ?
N3 H1 . 0.9027 ?
N4 N5 . 1.247(3) ?
N4 C2 . 1.395(3) ?
N5 N6 . 1.123(3) ?
N7 C2 . 1.324(3) ?
N7 C1 . 1.340(3) ?
O3 N8 . 1.226(3) ?
O4 N8 . 1.222(3) ?
N8 C3 . 1.451(3) ?
N9 C3 . 1.312(3) ?
N9 N10 . 1.360(3) ?
N10 C4 . 1.329(3) ?
N10 H3 . 0.8854 ?
N11 N12 . 1.245(3) ?
N11 C4 . 1.400(3) ?
N12 N13 . 1.127(3) ?
N14 C4 . 1.328(3) ?
N14 C3 . 1.343(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N15 P1 C5 . . 113.75(11) ?
N15 P1 C16 . . 109.56(10) ?
C5 P1 C16 . . 106.43(10) ?
N15 P1 C22 . . 111.51(10) ?
C5 P1 C22 . . 107.17(10) ?
C16 P1 C22 . . 108.16(10) ?
N15 P2 C23 . . 110.49(10) ?
N15 P2 C35 . . 113.43(10) ?
C23 P2 C35 . . 109.01(10) ?
N15 P2 C34 . . 111.02(11) ?
C23 P2 C34 . . 105.65(10) ?
C35 P2 C34 . . 106.89(10) ?
P2 N15 P1 . . 168.27(15) ?
C6 C5 C10 . . 119.4(2) ?
C6 C5 P1 . . 119.83(17) ?
C10 C5 P1 . . 120.63(17) ?
C7 C6 C5 . . 120.1(2) ?
C7 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
C8 C7 C6 . . 120.0(2) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C9 C8 C7 . . 120.5(2) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 120.0(2) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C5 . . 120.1(2) ?
C9 C10 H10 . . 119.9 ?
C5 C10 H10 . . 119.9 ?
C16 C11 C12 . . 119.8(2) ?
C16 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C13 C12 C11 . . 120.3(2) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.3(2) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.1(2) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C16 . . 119.8(2) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
C11 C16 C15 . . 119.7(2) ?
C11 C16 P1 . . 122.30(16) ?
C15 C16 P1 . . 118.00(17) ?
C22 C17 C18 . . 120.3(3) ?
C22 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C19 C18 C17 . . 120.0(3) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C18 C19 C20 . . 120.1(2) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C19 C20 C21 . . 120.4(3) ?
C19 C20 H20 . . 119.8 ?
C21 C20 H20 . . 119.8 ?
C22 C21 C20 . . 119.5(3) ?
C22 C21 H21 . . 120.3 ?
C20 C21 H21 . . 120.3 ?
C21 C22 C17 . . 119.7(2) ?
C21 C22 P1 . . 118.54(18) ?
C17 C22 P1 . . 121.71(18) ?
C28 C23 C24 . . 119.9(2) ?
C28 C23 P2 . . 118.83(17) ?
C24 C23 P2 . . 120.98(17) ?
C25 C24 C23 . . 119.7(2) ?
C25 C24 H24 . . 120.1 ?
C23 C24 H24 . . 120.1 ?
C26 C25 C24 . . 119.6(2) ?
C26 C25 H25 . . 120.2 ?
C24 C25 H25 . . 120.2 ?
C27 C26 C25 . . 121.0(2) ?
C27 C26 H26 . . 119.5 ?
C25 C26 H26 . . 119.5 ?
C26 C27 C28 . . 119.9(2) ?
C26 C27 H27 . . 120.0 ?
C28 C27 H27 . . 120.0 ?
C23 C28 C27 . . 119.8(2) ?
C23 C28 H28 . . 120.1 ?
C27 C28 H28 . . 120.1 ?
C34 C29 C30 . . 119.7(2) ?
C34 C29 H29 . . 120.1 ?
C30 C29 H29 . . 120.1 ?
C31 C30 C29 . . 120.3(2) ?
C31 C30 H30 . . 119.9 ?
C29 C30 H30 . . 119.9 ?
C30 C31 C32 . . 120.2(2) ?
C30 C31 H31 . . 119.9 ?
C32 C31 H31 . . 119.9 ?
C31 C32 C33 . . 120.1(2) ?
C31 C32 H32 . . 119.9 ?
C33 C32 H32 . . 119.9 ?
C32 C33 C34 . . 119.8(2) ?
C32 C33 H33 . . 120.1 ?
C34 C33 H33 . . 120.1 ?
C29 C34 C33 . . 119.9(2) ?
C29 C34 P2 . . 119.22(17) ?
C33 C34 P2 . . 120.63(17) ?
C38 C35 C40 . . 119.8(2) ?
C38 C35 P2 . . 122.18(16) ?
C40 C35 P2 . . 118.02(17) ?
C37 C36 C38 . . 119.7(2) ?
C37 C36 H36 . . 120.1 ?
C38 C36 H36 . . 120.1 ?
C39 C37 C36 . . 120.6(2) ?
C39 C37 H37 . . 119.7 ?
C36 C37 H37 . . 119.7 ?
C35 C38 C36 . . 120.1(2) ?
C35 C38 H38 . . 119.9 ?
C36 C38 H38 . . 119.9 ?
C37 C39 C40 . . 120.4(2) ?
C37 C39 H39 . . 119.8 ?
C40 C39 H39 . . 119.8 ?
C39 C40 C35 . . 119.4(2) ?
C39 C40 H40 . . 120.3 ?
C35 C40 H40 . . 120.3 ?
O2 N1 O1 . . 124.7(2) ?
O2 N1 C1 . . 118.2(2) ?
O1 N1 C1 . . 117.1(2) ?
C1 N2 N3 . . 101.4(2) ?
C2 N3 N2 . . 107.59(19) ?
C2 N3 H1 . . 129.5 ?
N2 N3 H1 . . 122.9 ?
N5 N4 C2 . . 114.5(2) ?
N6 N5 N4 . . 171.4(3) ?
C2 N7 C1 . . 98.9(2) ?
N2 C1 N7 . . 118.3(2) ?
N2 C1 N1 . . 120.4(2) ?
N7 C1 N1 . . 121.3(2) ?
N7 C2 N3 . . 113.9(2) ?
N7 C2 N4 . . 127.2(2) ?
N3 C2 N4 . . 119.0(2) ?
O4 N8 O3 . . 124.7(2) ?
O4 N8 C3 . . 117.7(2) ?
O3 N8 C3 . . 117.6(2) ?
C3 N9 N10 . . 101.9(2) ?
C4 N10 N9 . . 107.34(19) ?
C4 N10 H3 . . 127.3 ?
N9 N10 H3 . . 123.2 ?
N12 N11 C4 . . 114.7(2) ?
N13 N12 N11 . . 171.5(3) ?
C4 N14 C3 . . 98.7(2) ?
N9 C3 N14 . . 118.1(2) ?
N9 C3 N8 . . 120.4(2) ?
N14 C3 N8 . . 121.5(2) ?
N14 C4 N10 . . 114.0(2) ?
N14 C4 N11 . . 127.1(2) ?
N10 C4 N11 . . 118.8(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C23 P2 N15 P1 . . . . -105.3(7) ?
C35 P2 N15 P1 . . . . 17.4(8) ?
C34 P2 N15 P1 . . . . 137.8(7) ?
C5 P1 N15 P2 . . . . 41.3(7) ?
C16 P1 N15 P2 . . . . 160.3(7) ?
C22 P1 N15 P2 . . . . -80.0(7) ?
N15 P1 C5 C6 . . . . 156.78(18) ?
C16 P1 C5 C6 . . . . 36.0(2) ?
C22 P1 C5 C6 . . . . -79.5(2) ?
N15 P1 C5 C10 . . . . -28.2(2) ?
C16 P1 C5 C10 . . . . -148.94(17) ?
C22 P1 C5 C10 . . . . 95.52(19) ?
C10 C5 C6 C7 . . . . -1.9(4) ?
P1 C5 C6 C7 . . . . 173.18(19) ?
C5 C6 C7 C8 . . . . 1.8(4) ?
C6 C7 C8 C9 . . . . 0.0(4) ?
C7 C8 C9 C10 . . . . -1.6(4) ?
C8 C9 C10 C5 . . . . 1.4(3) ?
C6 C5 C10 C9 . . . . 0.3(3) ?
P1 C5 C10 C9 . . . . -174.72(17) ?
C16 C11 C12 C13 . . . . -0.2(4) ?
C11 C12 C13 C14 . . . . -0.3(5) ?
C12 C13 C14 C15 . . . . 0.4(4) ?
C13 C14 C15 C16 . . . . 0.1(4) ?
C12 C11 C16 C15 . . . . 0.7(4) ?
C12 C11 C16 P1 . . . . 179.5(2) ?
C14 C15 C16 C11 . . . . -0.6(3) ?
C14 C15 C16 P1 . . . . -179.53(18) ?
N15 P1 C16 C11 . . . . 129.9(2) ?
C5 P1 C16 C11 . . . . -106.7(2) ?
C22 P1 C16 C11 . . . . 8.2(2) ?
N15 P1 C16 C15 . . . . -51.2(2) ?
C5 P1 C16 C15 . . . . 72.19(19) ?
C22 P1 C16 C15 . . . . -172.93(17) ?
C22 C17 C18 C19 . . . . 0.1(4) ?
C17 C18 C19 C20 . . . . -1.2(5) ?
C18 C19 C20 C21 . . . . 1.6(5) ?
C19 C20 C21 C22 . . . . -0.8(6) ?
C20 C21 C22 C17 . . . . -0.3(5) ?
C20 C21 C22 P1 . . . . 178.3(3) ?
C18 C17 C22 C21 . . . . 0.7(4) ?
C18 C17 C22 P1 . . . . -177.8(2) ?
N15 P1 C22 C21 . . . . -42.4(2) ?
C5 P1 C22 C21 . . . . -167.5(2) ?
C16 P1 C22 C21 . . . . 78.1(2) ?
N15 P1 C22 C17 . . . . 136.1(2) ?
C5 P1 C22 C17 . . . . 11.0(2) ?
C16 P1 C22 C17 . . . . -103.3(2) ?
N15 P2 C23 C28 . . . . 29.9(2) ?
C35 P2 C23 C28 . . . . -95.41(19) ?
C34 P2 C23 C28 . . . . 150.03(18) ?
N15 P2 C23 C24 . . . . -144.49(18) ?
C35 P2 C23 C24 . . . . 90.23(19) ?
C34 P2 C23 C24 . . . . -24.3(2) ?
C28 C23 C24 C25 . . . . -1.1(3) ?
P2 C23 C24 C25 . . . . 173.25(17) ?
C23 C24 C25 C26 . . . . -0.7(3) ?
C24 C25 C26 C27 . . . . 2.4(4) ?
C25 C26 C27 C28 . . . . -2.3(4) ?
C24 C23 C28 C27 . . . . 1.2(4) ?
P2 C23 C28 C27 . . . . -173.25(19) ?
C26 C27 C28 C23 . . . . 0.5(4) ?
C34 C29 C30 C31 . . . . -0.4(3) ?
C29 C30 C31 C32 . . . . 1.7(4) ?
C30 C31 C32 C33 . . . . -1.3(4) ?
C31 C32 C33 C34 . . . . -0.5(4) ?
C30 C29 C34 C33 . . . . -1.4(3) ?
C30 C29 C34 P2 . . . . 172.37(16) ?
C32 C33 C34 C29 . . . . 1.8(3) ?
C32 C33 C34 P2 . . . . -171.83(19) ?
N15 P2 C34 C29 . . . . 29.8(2) ?
C23 P2 C34 C29 . . . . -90.05(18) ?
C35 P2 C34 C29 . . . . 153.93(17) ?
N15 P2 C34 C33 . . . . -156.57(18) ?
C23 P2 C34 C33 . . . . 83.62(19) ?
C35 P2 C34 C33 . . . . -32.4(2) ?
N15 P2 C35 C38 . . . . -129.59(19) ?
C23 P2 C35 C38 . . . . -6.0(2) ?
C34 P2 C35 C38 . . . . 107.72(19) ?
N15 P2 C35 C40 . . . . 51.6(2) ?
C23 P2 C35 C40 . . . . 175.13(17) ?
C34 P2 C35 C40 . . . . -71.11(19) ?
C38 C36 C37 C39 . . . . -0.9(4) ?
C40 C35 C38 C36 . . . . 0.7(3) ?
P2 C35 C38 C36 . . . . -178.07(18) ?
C37 C36 C38 C35 . . . . 0.2(4) ?
C36 C37 C39 C40 . . . . 0.7(4) ?
C37 C39 C40 C35 . . . . 0.3(3) ?
C38 C35 C40 C39 . . . . -1.0(3) ?
P2 C35 C40 C39 . . . . 177.91(18) ?
C1 N2 N3 C2 . . . . 0.7(2) ?
N3 N2 C1 N7 . . . . -0.7(3) ?
N3 N2 C1 N1 . . . . -179.5(2) ?
C2 N7 C1 N2 . . . . 0.3(3) ?
C2 N7 C1 N1 . . . . 179.1(2) ?
O2 N1 C1 N2 . . . . -0.8(4) ?
O1 N1 C1 N2 . . . . -179.0(2) ?
O2 N1 C1 N7 . . . . -179.6(2) ?
O1 N1 C1 N7 . . . . 2.2(4) ?
C1 N7 C2 N3 . . . . 0.2(3) ?
C1 N7 C2 N4 . . . . -178.6(2) ?
N2 N3 C2 N7 . . . . -0.7(3) ?
N2 N3 C2 N4 . . . . 178.3(2) ?
N5 N4 C2 N7 . . . . 5.2(4) ?
N5 N4 C2 N3 . . . . -173.6(2) ?
C3 N9 N10 C4 . . . . -0.4(3) ?
N10 N9 C3 N14 . . . . 0.5(3) ?
N10 N9 C3 N8 . . . . 179.2(2) ?
C4 N14 C3 N9 . . . . -0.4(3) ?
C4 N14 C3 N8 . . . . -179.1(2) ?
O4 N8 C3 N9 . . . . 3.3(4) ?
O3 N8 C3 N9 . . . . -177.9(2) ?
O4 N8 C3 N14 . . . . -178.1(2) ?
O3 N8 C3 N14 . . . . 0.8(4) ?
C3 N14 C4 N10 . . . . 0.1(3) ?
C3 N14 C4 N11 . . . . -179.4(2) ?
N9 N10 C4 N14 . . . . 0.2(3) ?
N9 N10 C4 N11 . . . . 179.7(2) ?
N12 N11 C4 N14 . . . . -6.3(4) ?
N12 N11 C4 N10 . . . . 174.2(2) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1013935'
_audit_update_record             
;
2014-07-14 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C4 H7 N5 O'
_chemical_formula_sum            'C4 H7 N5 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         141.15

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.25150(10)
_cell_length_b                   7.69060(10)
_cell_length_c                   8.49150(10)
_cell_angle_alpha                67.2290(10)
_cell_angle_beta                 85.4460(10)
_cell_angle_gamma                70.1300(10)
_cell_volume                     296.854(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             148

_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            35219
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         36.40
_diffrn_reflns_theta_full        36.40
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             2865
_reflns_number_gt                2727
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0820
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_number_reflns         2865
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.0425P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.054(11)

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XS 2013/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.60431(9) 0.71334(6) 0.00221(6) 0.00969(8) Uani d . . . 1 . .
C C2 0.26754(9) 0.71975(6) 0.15887(6) 0.00974(8) Uani d . . . 1 . .
C C3 0.46799(9) 0.37198(7) 0.37460(6) 0.01160(8) Uani d . . . 1 . .
C C4 0.71507(10) 0.19034(7) 0.41216(6) 0.01504(9) Uani d . . . 1 . .
H H4A 0.6917 0.0818 0.5147 0.023 Uiso calc U . R 1 . .
H H4B 0.8733 0.2213 0.4315 0.023 Uiso calc U . R 1 . .
H H4C 0.7425 0.1486 0.3149 0.023 Uiso calc U . R 1 . .
H H1 0.735(2) 0.9058(18) -0.1643(15) 0.028(3) Uiso d . . . 1 . .
H H2 0.923(2) 0.7007(17) -0.1315(14) 0.024(2) Uiso d . . . 1 . .
H H3 -0.096(2) 0.8906(18) 0.1635(15) 0.029(3) Uiso d . . . 1 . .
H H4 -0.013(2) 0.6884(17) 0.3146(14) 0.023(2) Uiso d . . . 1 . .
N N1 0.46568(8) 0.53332(6) 0.22513(5) 0.01016(7) Uani d . . . 1 . .
N N2 0.68752(8) 0.53103(6) 0.12133(5) 0.01038(8) Uani d . . . 1 . .
N N3 0.34994(8) 0.83553(6) 0.01797(5) 0.01059(8) Uani d . . . 1 . .
N N4 0.75134(9) 0.77978(6) -0.13436(5) 0.01257(8) Uani d . . . 1 . .
N N5 0.03272(9) 0.77609(6) 0.22891(5) 0.01256(8) Uani d . . . 1 . .
O O1 0.27708(9) 0.38638(6) 0.46664(5) 0.01712(9) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.3174(6) ?
C1 N4 . 1.3673(6) ?
C1 N3 . 1.3788(6) ?
C2 N3 . 1.3292(6) ?
C2 N5 . 1.3349(6) ?
C2 N1 . 1.3818(6) ?
C3 O1 . 1.2228(6) ?
C3 N1 . 1.3870(6) ?
C3 C4 . 1.4918(7) ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
N1 N2 . 1.4034(6) ?
N4 H1 . 0.876(12) ?
N4 H2 . 0.898(12) ?
N5 H3 . 0.904(12) ?
N5 H4 . 0.863(11) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N4 . . 123.45(4) ?
N2 C1 N3 . . 116.03(4) ?
N4 C1 N3 . . 120.47(4) ?
N3 C2 N5 . . 125.37(4) ?
N3 C2 N1 . . 109.63(4) ?
N5 C2 N1 . . 124.97(4) ?
O1 C3 N1 . . 119.86(4) ?
O1 C3 C4 . . 124.58(4) ?
N1 C3 C4 . . 115.55(4) ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C2 N1 C3 . . 128.45(4) ?
C2 N1 N2 . . 109.02(4) ?
C3 N1 N2 . . 122.40(4) ?
C1 N2 N1 . . 101.90(4) ?
C2 N3 C1 . . 103.41(4) ?
C1 N4 H1 . . 113.0(8) ?
C1 N4 H2 . . 116.7(7) ?
H1 N4 H2 . . 113.2(11) ?
C2 N5 H3 . . 117.0(8) ?
C2 N5 H4 . . 119.5(7) ?
H3 N5 H4 . . 119.9(10) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1013936'
_audit_update_record             
;
2014-07-14 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            HDNT1
_chemical_formula_moiety         'C5 H7 N5 O4'
_chemical_formula_sum            'C5 H7 N5 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         201.16

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.4402(19)
_cell_length_b                   10.611(2)
_cell_length_c                   17.296(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1732.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4641
_cell_measurement_theta_min      2.3550
_cell_measurement_theta_max      27.4240
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3660

_diffrn_reflns_number            13391
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             2124
_reflns_number_gt                1538
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1074
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         2124
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.6327P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.192
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'SMART V5.632'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.32659(16) 0.09436(14) 0.33996(9) 0.0289(3) Uani d . . . 1 . .
C C2 0.46877(16) 0.21658(14) 0.29449(9) 0.0283(3) Uani d . . . 1 . .
C C3 0.65767(17) 0.19786(17) 0.40377(10) 0.0370(4) Uani d . . . 1 . .
H H3 0.7182 0.2546 0.3715 0.044 Uiso calc U . R 1 . .
C C4 0.7329(2) 0.07375(19) 0.41323(11) 0.0490(5) Uani d . . . 1 . .
H H4A 0.8259 0.088 0.4368 0.073 Uiso calc U . R 1 . .
H H4B 0.745 0.0341 0.3625 0.073 Uiso calc U . R 1 . .
H H4C 0.6766 0.0183 0.4466 0.073 Uiso calc U . R 1 . .
C C5 0.6259(2) 0.2637(2) 0.47975(11) 0.0494(5) Uani d . . . 1 . .
H H5A 0.7149 0.2829 0.5064 0.074 Uiso calc U . R 1 . .
H H5B 0.5677 0.2086 0.5123 0.074 Uiso calc U . R 1 . .
H H5C 0.5744 0.3422 0.4695 0.074 Uiso calc U . R 1 . .
N N1 0.52142(13) 0.17584(12) 0.36226(7) 0.0290(3) Uani d . . . 1 . .
N N2 0.42717(13) 0.09428(13) 0.39278(8) 0.0317(3) Uani d . . . 1 . .
N N3 0.34515(14) 0.16716(12) 0.27788(7) 0.0306(3) Uani d . . . 1 . .
N N4 0.20218(14) 0.01512(13) 0.34775(8) 0.0350(3) Uani d . . . 1 . .
N N5 0.53883(15) 0.30410(13) 0.24215(8) 0.0358(3) Uani d . . . 1 . .
O O1 0.11097(13) 0.02530(13) 0.29827(8) 0.0497(4) Uani d . . . 1 . .
O O2 0.19808(14) -0.05849(14) 0.40175(8) 0.0538(4) Uani d . . . 1 . .
O O3 0.49434(16) 0.30828(14) 0.17630(8) 0.0589(4) Uani d . . . 1 . .
O O4 0.63671(13) 0.36692(11) 0.26755(7) 0.0412(3) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.318(2) ?
C1 N3 . 1.334(2) ?
C1 N4 . 1.451(2) ?
C2 N3 . 1.311(2) ?
C2 N1 . 1.345(2) ?
C2 N5 . 1.456(2) ?
C3 N1 . 1.491(2) ?
C3 C4 . 1.505(3) ?
C3 C5 . 1.518(2) ?
C3 H3 . 1.0 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
N1 N2 . 1.3488(18) ?
N4 O2 . 1.2182(19) ?
N4 O1 . 1.2188(18) ?
N5 O3 . 1.2147(19) ?
N5 O4 . 1.2211(18) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N3 . . 117.62(14) ?
N2 C1 N4 . . 121.24(14) ?
N3 C1 N4 . . 121.11(14) ?
N3 C2 N1 . . 113.05(14) ?
N3 C2 N5 . . 121.54(14) ?
N1 C2 N5 . . 125.39(14) ?
N1 C3 C4 . . 108.78(14) ?
N1 C3 C5 . . 108.55(14) ?
C4 C3 C5 . . 113.71(15) ?
N1 C3 H3 . . 108.6 ?
C4 C3 H3 . . 108.6 ?
C5 C3 H3 . . 108.6 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C2 N1 N2 . . 107.67(12) ?
C2 N1 C3 . . 133.48(13) ?
N2 N1 C3 . . 118.75(13) ?
C1 N2 N1 . . 101.75(13) ?
C2 N3 C1 . . 99.91(13) ?
O2 N4 O1 . . 124.94(14) ?
O2 N4 C1 . . 117.95(14) ?
O1 N4 C1 . . 117.09(14) ?
O3 N5 O4 . . 125.38(15) ?
O3 N5 C2 . . 116.70(14) ?
O4 N5 C2 . . 117.92(14) ?

####################################################################### 
# 
# 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_C5H8N4O3
_database_code_depnum_ccdc_archive 'CCDC 1013937'
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 N4 O3'
_chemical_formula_sum            'C5 H8 N4 O3'
_chemical_formula_weight         172.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6336(8)
_cell_length_b                   7.6993(8)
_cell_length_c                   8.5129(9)
_cell_angle_alpha                83.636(5)
_cell_angle_beta                 73.035(5)
_cell_angle_gamma                65.784(6)
_cell_volume                     379.25(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4459
_cell_measurement_theta_min      5.4332
_cell_measurement_theta_max      67.5252

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             180
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.041
_exptl_absorpt_coefficient_mu    1.086
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   
'Sheldrick, G.M. (2008) SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II DUO diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8069
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.433
_diffrn_reflns_theta_max         67.947
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1315
_reflns_number_gt                1209
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 v2010.9-0 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 v2010.9-0 (Bruker, 2010)'
_computing_data_reduction        'SAINT v7.66A (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0512P)²+0.0922P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1315
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20328(17) 0.58421(14) 0.59219(13) 0.0246(3) Uani 1 1 d . . . . .
N2 N 0.34022(17) 0.33772(15) 0.42458(13) 0.0240(3) Uani 1 1 d . . . . .
N3 N 0.35875(17) 0.25940(15) 0.57415(13) 0.0250(3) Uani 1 1 d . . . . .
N4 N 0.26610(18) 0.39695(15) 0.83854(14) 0.0276(3) Uani 1 1 d . . . . .
O1 O 0.21743(15) 0.63430(12) 0.30799(11) 0.0275(2) Uani 1 1 d . . . . .
O2 O 0.20609(18) 0.54396(14) 0.91399(12) 0.0364(3) Uani 1 1 d . . . . .
O3 O 0.32199(17) 0.23640(13) 0.89652(12) 0.0348(3) Uani 1 1 d . . . . .
C1 C 0.2746(2) 0.41299(17) 0.66505(15) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.2487(2) 0.52883(17) 0.43911(15) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.1138(2) 0.84064(17) 0.33731(17) 0.0270(3) Uani 1 1 d . . . . .
H3A H 0.216(3) 0.871(2) 0.3803(18) 0.026(4) Uiso 1 1 d . . . . .
H3B H -0.033(3) 0.869(2) 0.4205(18) 0.025(4) Uiso 1 1 d . . . . .
C4 C 0.0859(3) 0.9344(2) 0.17745(19) 0.0343(3) Uani 1 1 d . . . . .
H4A H 0.232(3) 0.901(2) 0.097(2) 0.043(5) Uiso 1 1 d . . . . .
H4B H 0.013(3) 1.071(2) 0.194(2) 0.038(4) Uiso 1 1 d . . . . .
H4C H -0.013(3) 0.893(2) 0.138(2) 0.044(5) Uiso 1 1 d . . . . .
C5 C 0.4190(3) 0.2228(2) 0.27623(17) 0.0307(3) Uani 1 1 d . . . . .
H5A H 0.537(4) 0.253(3) 0.199(3) 0.064(6) Uiso 1 1 d . . . . .
H5B H 0.290(4) 0.247(3) 0.237(3) 0.061(6) Uiso 1 1 d . . . . .
H5C H 0.483(3) 0.092(3) 0.308(2) 0.045(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3264(16) . ?
N1 C1 1.3508(16) . ?
N2 C2 1.3464(16) . ?
N2 N3 1.3640(15) . ?
N2 C5 1.4607(17) . ?
N3 C1 1.3108(16) . ?
N4 O2 1.2225(15) . ?
N4 O3 1.2266(15) . ?
N4 C1 1.4548(17) . ?
O1 C2 1.3208(16) . ?
O1 C3 1.4665(15) . ?
C3 C4 1.4922(19) . ?
C3 H3A 0.968(16) . ?
C3 H3B 0.979(15) . ?
C4 H4A 0.962(18) . ?
C4 H4B 0.969(17) . ?
C4 H4C 0.980(19) . ?
C5 H5A 0.96(2) . ?
C5 H5B 0.95(2) . ?
C5 H5C 0.958(19) . ?

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
C2 N1 C1 100.08(10) . . ?
C2 N2 N3 109.13(10) . . ?
C2 N2 C5 128.16(11) . . ?
N3 N2 C5 122.68(10) . . ?
C1 N3 N2 100.86(10) . . ?
O2 N4 O3 125.45(12) . . ?
O2 N4 C1 117.44(11) . . ?
O3 N4 C1 117.11(11) . . ?
C2 O1 C3 115.20(10) . . ?
N3 C1 N1 118.24(12) . . ?
N3 C1 N4 120.19(11) . . ?
N1 C1 N4 121.55(11) . . ?
O1 C2 N1 128.84(11) . . ?
O1 C2 N2 119.46(11) . . ?
N1 C2 N2 111.70(11) . . ?
O1 C3 C4 107.27(11) . . ?
O1 C3 H3A 107.1(8) . . ?
C4 C3 H3A 113.1(9) . . ?
O1 C3 H3B 106.7(8) . . ?
C4 C3 H3B 112.5(8) . . ?
H3A C3 H3B 109.8(12) . . ?
C3 C4 H4A 110.7(10) . . ?
C3 C4 H4B 109.0(10) . . ?
H4A C4 H4B 109.4(14) . . ?
C3 C4 H4C 109.1(10) . . ?
H4A C4 H4C 109.6(15) . . ?
H4B C4 H4C 109.0(14) . . ?
N2 C5 H5A 108.5(13) . . ?
N2 C5 H5B 108.0(12) . . ?
H5A C5 H5B 113.7(18) . . ?
N2 C5 H5C 106.6(11) . . ?
H5A C5 H5C 109.0(15) . . ?
H5B C5 H5C 110.8(16) . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_C7H9N9O6
_database_code_depnum_ccdc_archive 'CCDC 1013938'
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C5 H7 N5 O4, C2 H2 N4 O2'
_chemical_formula_sum            'C7 H9 N9 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         315.23

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.472(2)
_cell_length_b                   11.272(2)
_cell_length_c                   23.860(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2547.5(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5729
_cell_measurement_theta_min      2.7464
_cell_measurement_theta_max      27.0851
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296

_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Bruker AXS, 2014)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14568
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             2921
_reflns_number_gt                2252
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1752
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         2921
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0973P)²+1.3970P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.566
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'SMART V5.632'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXTL XL 2014/7 (Bruker AXS, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXTL XL 2014/7 (Bruker AXS, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4690(2) 0.54038(19) 0.28211(9) 0.0325(5) Uani d . . . 1 . .
C C2 0.3362(2) 0.66278(19) 0.31512(9) 0.0318(5) Uani d . . . 1 . .
C C3 0.6759(2) 0.5700(2) 0.35162(10) 0.0384(5) Uani d . . . 1 . .
H H3 0.7333 0.5226 0.3245 0.046 Uiso calc U . R 1 . .
C C4 0.7497(3) 0.6874(3) 0.36041(12) 0.0500(7) Uani d . . . 1 . .
H H4A 0.6957 0.7355 0.387 0.075 Uiso calc U . R 1 . .
H H4B 0.7566 0.7294 0.3246 0.075 Uiso calc U . R 1 . .
H H4C 0.8446 0.6733 0.3753 0.075 Uiso calc U . R 1 . .
C C5 0.6581(3) 0.4979(3) 0.40337(11) 0.0483(6) Uani d . . . 1 . .
H H5A 0.6113 0.4229 0.394 0.072 Uiso calc U . R 1 . .
H H5B 0.6004 0.5419 0.4304 0.072 Uiso calc U . R 1 . .
H H5C 0.7509 0.4815 0.4198 0.072 Uiso calc U . R 1 . .
C C6 -0.0373(2) 0.27222(18) 0.49235(8) 0.0260(4) Uani d . . . 1 . .
H H6 -0.1265 0.2387 0.5012 0.031 Uiso calc U . R 1 . .
C C7 0.1138(2) 0.38134(19) 0.46324(9) 0.0312(5) Uani d . . . 1 . .
N N1 0.3429(2) 0.58454(17) 0.27330(8) 0.0346(4) Uani d . . . 1 . .
N N2 0.53433(19) 0.58962(16) 0.32626(8) 0.0316(4) Uani d . . . 1 . .
N N3 0.4470(2) 0.67112(16) 0.34864(8) 0.0339(4) Uani d . . . 1 . .
N N4 0.5290(2) 0.44914(18) 0.24604(9) 0.0404(5) Uani d . . . 1 . .
N N5 0.2135(2) 0.73776(18) 0.32244(8) 0.0382(5) Uani d . . . 1 . .
N N6 0.18120(19) 0.29214(18) 0.48784(8) 0.0358(4) Uani d . . . 1 . .
N N7 0.0808(2) 0.22207(18) 0.50604(9) 0.0398(5) Uani d . . . 1 . .
H H7 0.0915 0.1545 0.524 0.048 Uiso calc U . R 1 . .
N N8 -0.02401(19) 0.37352(18) 0.46515(8) 0.0373(5) Uani d . . . 1 . .
N N9 0.1881(2) 0.48022(18) 0.43829(9) 0.0424(5) Uani d . . . 1 . .
O O1 0.62673(18) 0.39039(15) 0.26430(8) 0.0472(5) Uani d . . . 1 . .
O O2 0.4762(2) 0.4383(2) 0.20024(9) 0.0674(7) Uani d . . . 1 . .
O O3 0.2170(2) 0.81272(17) 0.35900(8) 0.0522(5) Uani d . . . 1 . .
O O4 0.11397(19) 0.72067(19) 0.29115(8) 0.0551(5) Uani d . . . 1 . .
O O5 0.3150(2) 0.48409(18) 0.44612(9) 0.0576(6) Uani d . . . 1 . .
O O6 0.1178(2) 0.55195(17) 0.41181(9) 0.0620(6) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.311(3) ?
C1 N2 . 1.342(3) ?
C1 N4 . 1.456(3) ?
C2 N3 . 1.323(3) ?
C2 N1 . 1.333(3) ?
C2 N5 . 1.448(3) ?
C3 N2 . 1.487(3) ?
C3 C5 . 1.488(3) ?
C3 C4 . 1.511(4) ?
C3 H3 . 1.0 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 N7 . 1.295(3) ?
C6 N8 . 1.320(3) ?
C6 H6 . 0.95 ?
C7 N6 . 1.328(3) ?
C7 N9 . 1.446(3) ?
N2 N3 . 1.346(3) ?
N4 O2 . 1.208(3) ?
N4 O1 . 1.219(3) ?
N5 O3 . 1.215(3) ?
N5 O4 . 1.218(3) ?
N6 N7 . 1.310(3) ?
N7 H7 . 0.88 ?
N9 O5 . 1.217(3) ?
N9 O6 . 1.223(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 112.9(2) ?
N1 C1 N4 . . 121.9(2) ?
N2 C1 N4 . . 125.2(2) ?
N3 C2 N1 . . 117.5(2) ?
N3 C2 N5 . . 121.5(2) ?
N1 C2 N5 . . 120.98(19) ?
N2 C3 C5 . . 108.5(2) ?
N2 C3 C4 . . 110.1(2) ?
C5 C3 C4 . . 114.5(2) ?
N2 C3 H3 . . 107.8 ?
C5 C3 H3 . . 107.8 ?
C4 C3 H3 . . 107.8 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C5 H5A . . 109.5 ?
C3 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C3 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N7 C6 N8 . . 114.81(19) ?
N7 C6 H6 . . 122.6 ?
N8 C6 H6 . . 122.6 ?
N6 C7 N9 . . 122.1(2) ?
C1 N1 C2 . . 100.04(18) ?
C1 N2 N3 . . 108.10(18) ?
C1 N2 C3 . . 132.33(19) ?
N3 N2 C3 . . 119.57(18) ?
C2 N3 N2 . . 101.47(18) ?
O2 N4 O1 . . 125.7(2) ?
O2 N4 C1 . . 116.4(2) ?
O1 N4 C1 . . 118.0(2) ?
O3 N5 O4 . . 124.9(2) ?
O3 N5 C2 . . 118.07(19) ?
O4 N5 C2 . . 117.1(2) ?
N7 N6 C7 . . 104.73(18) ?
C6 N7 N6 . . 106.26(19) ?
C6 N7 H7 . . 126.9 ?
N6 N7 H7 . . 126.9 ?
O5 N9 O6 . . 126.4(2) ?
O5 N9 C7 . . 116.4(2) ?
O6 N9 C7 . . 117.2(2) ?

####################################################################### 
# 
# 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_DisorderedPNPDNT-azidonitrotriazole
_database_code_depnum_ccdc_archive 'CCDC 1045452'
_audit_update_record             
;
2015-01-24 deposited with the CCDC.
2015-03-26 downloaded from the CCDC.
;
_chemical_name_systematic        
'Mixed bis (triphenylphosphoranylidene)ammonium 3,5-dinitro-1,2,4-triazolate /bis (triphenylphosphoranylidene)ammonium 5-azido-3-nitro-1,2,4-triazolate'
_chemical_name_common            PNPDNT/PNPazidonitrotriazolate
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H30 N6.51 O3.49 P2'
_chemical_formula_iupac          ?
_chemical_formula_weight         695.60

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8448(6)
_cell_length_b                   11.9539(7)
_cell_length_c                   14.4364(8)
_cell_angle_alpha                67.1350(10)
_cell_angle_beta                 89.7880(10)
_cell_angle_gamma                76.1090(10)
_cell_volume                     1665.59(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9922
_cell_measurement_theta_min      2.3483
_cell_measurement_theta_max      30.8041
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.630
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.265
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             723

_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Bruker AXS, 2014)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            42188
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         31.12
_diffrn_reflns_theta_full        31.12
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
'The DNT and azido nitro triazolate were part of a disorder with 75%25% occupancy factors, respectively'

_reflns_number_total             10304
_reflns_number_gt                8327
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1019
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_refine_ls_number_reflns         10304
_refine_ls_number_parameters     659
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+1.0479P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
'Bruker Instrument Service v2012.12.0.3 (Bruker AXS, 2012)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.9428(14) 0.0582(12) 0.7777(11) 0.0148(15) Uani d . P . 0.743(4) A 1
C C3 1.0737(3) 0.1239(3) 0.6898(2) 0.0147(5) Uani d . P . 0.743(4) A 1
N N2 1.0062(4) 0.1438(4) 0.7618(4) 0.0170(6) Uani d . P . 0.743(4) A 1
N N3 1.0547(4) 0.0339(4) 0.6620(4) 0.0189(6) Uani d . P . 0.743(4) A 1
N N4 0.9636(13) -0.0107(10) 0.7218(10) 0.0179(11) Uani d . P . 0.743(4) A 1
N N5 1.16267(19) 0.19648(17) 0.64199(13) 0.0196(4) Uani d . P . 0.743(4) A 1
N N6 0.8522(4) 0.0366(5) 0.8533(3) 0.0170(5) Uani d . P . 0.743(4) A 1
O O1 1.22146(14) 0.17132(16) 0.57733(13) 0.0295(4) Uani d . P . 0.743(4) A 1
O O2 1.17236(17) 0.27995(15) 0.66839(14) 0.0365(5) Uani d . P . 0.743(4) A 1
O O3 0.7804(4) -0.0296(4) 0.8487(3) 0.0228(6) Uani d . P . 0.743(4) A 1
O O4 0.8525(4) 0.0813(4) 0.9136(3) 0.0305(6) Uani d . P . 0.743(4) A 1
C C1A 1.0838(9) 0.0865(9) 0.6806(7) 0.0157(15) Uani d . P . 0.257(4) A 2
C C2A 0.946(4) 0.042(3) 0.770(3) 0.014(5) Uani d . P . 0.257(4) A 2
N N1A 1.1858(5) 0.1323(6) 0.6258(5) 0.0295(14) Uani d . P . 0.257(4) A 2
N N2A 1.2199(8) 0.2102(6) 0.6494(5) 0.0370(16) Uani d . P . 0.257(4) A 2
N N3A 1.2580(8) 0.2824(7) 0.6587(6) 0.056(2) Uani d . P . 0.257(4) A 2
N N4A 1.0462(15) 0.0009(10) 0.6599(12) 0.028(2) Uani d . P . 0.257(4) A 2
N N5A 1.0305(12) 0.1211(12) 0.7501(11) 0.0195(19) Uani d . P . 0.257(4) A 2
N N6A 0.8655(16) 0.0385(18) 0.8441(14) 0.0324(18) Uani d . P . 0.257(4) A 2
O O1A 0.8779(11) 0.0961(12) 0.9066(10) 0.0324(18) Uani d . P . 0.257(4) A 2
O O2A 0.7793(16) -0.0148(15) 0.8613(12) 0.0324(18) Uani d . P . 0.257(4) A 2
N N4B 0.955(4) -0.028(3) 0.720(3) 0.027(5) Uani d . P . 0.257(4) A 2
C C010 0.66658(12) 0.19162(13) 0.15608(9) 0.0181(2) Uani d . . . 1.0 . .
C C012 0.35097(13) 0.54588(14) 0.45747(12) 0.0236(3) Uani d . . . 1.0 . .
C C013 -0.01031(12) 0.21868(12) 0.39702(10) 0.0200(2) Uani d . . . 1.0 . .
C C015 0.05556(13) 0.64821(13) 0.11279(11) 0.0221(3) Uani d . . . 1.0 . .
C C017 0.02578(15) 0.69403(14) -0.06469(11) 0.0274(3) Uani d . . . 1.0 . .
C C018 0.71470(13) 0.11730(14) 0.10376(11) 0.0233(3) Uani d . . . 1.0 . .
C C019 0.67831(15) 0.54711(14) 0.24273(11) 0.0283(3) Uani d . . . 1.0 . .
C C00A 0.55023(11) 0.41887(11) 0.21929(9) 0.0142(2) Uani d . . . 1.0 . .
C C01A 0.64215(14) 0.04669(14) 0.08390(11) 0.0244(3) Uani d . . . 1.0 . .
C C00B 0.54905(11) 0.18728(10) 0.39071(8) 0.0127(2) Uani d . . . 1.0 . .
C C01B -0.00587(15) 0.72524(13) 0.01696(11) 0.0276(3) Uani d . . . 1.0 . .
C C00C 0.46868(11) 0.16744(11) 0.46816(9) 0.0139(2) Uani d . . . 1.0 . .
C C01C 0.37844(14) 0.65832(14) 0.39866(14) 0.0299(3) Uani d . . . 1.0 . .
C C00D 0.47068(12) 0.12611(12) 0.16693(9) 0.0165(2) Uani d . . . 1.0 . .
C C01D 0.35777(14) 0.70591(13) 0.29462(14) 0.0291(3) Uani d . . . 1.0 . .
C C01E 0.63732(15) 0.63551(14) 0.14510(11) 0.0267(3) Uani d . . . 1.0 . .
C C00F 0.54421(11) 0.19596(11) 0.18820(9) 0.0139(2) Uani d . . . 1.0 . .
C C00G 0.10401(11) 0.37828(11) 0.32664(9) 0.0139(2) Uani d . . . 1.0 . .
C C00H 0.27995(11) 0.52879(11) 0.30608(10) 0.0156(2) Uani d . . . 1.0 . .
C C00I 0.52043(12) 0.09520(11) 0.56784(9) 0.0166(2) Uani d . . . 1.0 . .
C C00J 0.14922(11) 0.53798(11) 0.12649(9) 0.0159(2) Uani d . . . 1.0 . .
C C00K 0.30259(11) 0.48065(12) 0.41167(10) 0.0174(2) Uani d . . . 1.0 . .
C C00M 0.02967(12) 0.44980(12) 0.37327(10) 0.0183(2) Uani d . . . 1.0 . .
C C00N 0.17991(12) 0.50615(12) 0.04443(10) 0.0185(2) Uani d . . . 1.0 . .
C C00O 0.50982(12) 0.50845(12) 0.12083(9) 0.0175(2) Uani d . . . 1.0 . .
C C00P 0.68011(12) 0.13027(12) 0.41331(9) 0.0173(2) Uani d . . . 1.0 . .
C C00Q 0.73076(12) 0.05897(12) 0.51297(10) 0.0192(2) Uani d . . . 1.0 . .
C C00R 0.65107(13) 0.04277(11) 0.59021(9) 0.0182(2) Uani d . . . 1.0 . .
C C00S -0.06094(12) 0.40333(14) 0.43439(10) 0.0216(3) Uani d . . . 1.0 . .
C C00T -0.07989(12) 0.28769(13) 0.44692(10) 0.0209(3) Uani d . . . 1.0 . .
C C00U 0.08307(11) 0.26330(11) 0.33754(9) 0.0161(2) Uani d . . . 1.0 . .
C C00V 0.52010(14) 0.05131(13) 0.11495(10) 0.0221(3) Uani d . . . 1.0 . .
C C00W 0.11793(14) 0.58483(14) -0.05128(10) 0.0239(3) Uani d . . . 1.0 . .
C C00X 0.30758(13) 0.64216(12) 0.24739(11) 0.0220(3) Uani d . . . 1.0 . .
C C00Y 0.63473(13) 0.43881(12) 0.27994(10) 0.0208(3) Uani d . . . 1.0 . .
C C00Z 0.55306(14) 0.61652(13) 0.08404(10) 0.0223(3) Uani d . . . 1.0 . .
H H1 0.0325(17) 0.6740(17) 0.1670(14) 0.028(4) Uiso d . . . 1.0 . .
H H2 -0.0163(19) 0.7483(19) -0.1293(15) 0.038(5) Uiso d . . . 1.0 . .
H H3 0.2409(16) 0.4332(16) 0.0532(13) 0.021(4) Uiso d . . . 1.0 . .
H H4 0.4519(17) 0.4958(16) 0.0785(13) 0.024(4) Uiso d . . . 1.0 . .
H H5 0.6627(16) 0.3789(17) 0.3463(14) 0.026(4) Uiso d . . . 1.0 . .
H H6 0.2829(15) 0.4016(16) 0.4534(13) 0.020(4) Uiso d . . . 1.0 . .
H H7 0.3779(19) 0.782(2) 0.2517(15) 0.041(5) Uiso d . . . 1.0 . .
H H8 0.2919(16) 0.6744(17) 0.1764(14) 0.026(4) Uiso d . . . 1.0 . .
H H9 0.0423(15) 0.5310(15) 0.3635(12) 0.018(4) Uiso d . . . 1.0 . .
H H10 0.4665(17) 0.0062(17) 0.0979(14) 0.029(5) Uiso d . . . 1.0 . .
H H11 0.6790(19) -0.0058(18) 0.0478(15) 0.037(5) Uiso d . . . 1.0 . .
H H12 0.7377(15) 0.1368(15) 0.3594(12) 0.020(4) Uiso d . . . 1.0 . .
H H13 0.8220(17) 0.0203(16) 0.5269(13) 0.027(4) Uiso d . . . 1.0 . .
H H14 0.6876(16) -0.0058(16) 0.6595(13) 0.023(4) Uiso d . . . 1.0 . .
H H15 0.4645(16) 0.0848(16) 0.6187(13) 0.022(4) Uiso d . . . 1.0 . .
H H16 0.3782(15) 0.2007(15) 0.4528(12) 0.015(4) Uiso d . . . 1.0 . .
H H17 0.1337(16) 0.2128(16) 0.3052(13) 0.021(4) Uiso d . . . 1.0 . .
H H18 0.4111(19) 0.7033(19) 0.4312(15) 0.040(5) Uiso d . . . 1.0 . .
H H19 0.3673(17) 0.5104(17) 0.5319(14) 0.030(5) Uiso d . . . 1.0 . .
H H20 -0.0228(16) 0.1374(17) 0.4056(13) 0.026(4) Uiso d . . . 1.0 . .
H H21 -0.1407(17) 0.2563(16) 0.4891(13) 0.025(4) Uiso d . . . 1.0 . .
H H22 -0.1112(18) 0.4530(18) 0.4686(14) 0.032(5) Uiso d . . . 1.0 . .
H H23 -0.0721(19) 0.8002(19) 0.0079(15) 0.040(5) Uiso d . . . 1.0 . .
H H24 0.1397(18) 0.5602(18) -0.1072(15) 0.034(5) Uiso d . . . 1.0 . .
H H25 0.5256(17) 0.6780(17) 0.0169(14) 0.029(5) Uiso d . . . 1.0 . .
H H26 0.7385(19) 0.5600(18) 0.2852(15) 0.038(5) Uiso d . . . 1.0 . .
H H27 0.665(2) 0.711(2) 0.1187(17) 0.049(6) Uiso d . . . 1.0 . .
H H28 0.3867(16) 0.1344(15) 0.1845(13) 0.020(4) Uiso d . . . 1.0 . .
H H29 0.8001(18) 0.1125(18) 0.0836(14) 0.033(5) Uiso d . . . 1.0 . .
H H30 0.7177(17) 0.2420(17) 0.1672(14) 0.027(4) Uiso d . . . 1.0 . .
N N1 0.33265(9) 0.32030(9) 0.24823(8) 0.01404(19) Uani d . . . 1.0 . .
P P001 0.48399(3) 0.28456(3) 0.26219(2) 0.01146(7) Uani d . . . 1.0 . .
P P002 0.22510(3) 0.43577(3) 0.25100(2) 0.01212(7) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N2 . 1.314(14) ?
C2 N4 . 1.343(18) ?
C2 N6 . 1.456(14) ?
C3 N2 . 1.334(4) ?
C3 N3 . 1.341(4) ?
C3 N5 . 1.447(4) ?
N3 N4 . 1.376(15) ?
N5 O1 . 1.221(2) ?
N5 O2 . 1.224(3) ?
N6 O4 . 1.185(6) ?
N6 O3 . 1.254(5) ?
C1A N5A . 1.310(12) ?
C1A N4A . 1.320(10) ?
C1A N1A . 1.448(11) ?
C1A C2A . 2.00(3) ?
C2A N4B . 1.29(5) ?
C2A N6A . 1.37(4) ?
C2A N5A . 1.42(4) ?
N1A N2A . 1.238(9) ?
N2A N3A . 1.093(10) ?
N4A N4B . 1.33(5) ?
N6A O2A . 1.22(2) ?
N6A O1A . 1.35(2) ?
C010 C018 . 1.3884(18) ?
C010 C00F . 1.4000(16) ?
C012 C01C . 1.385(2) ?
C012 C00K . 1.3857(18) ?
C013 C00T . 1.3885(19) ?
C013 C00U . 1.3944(17) ?
C015 C01B . 1.3885(19) ?
C015 C00J . 1.4012(18) ?
C017 C00W . 1.385(2) ?
C017 C01B . 1.387(2) ?
C018 C01A . 1.386(2) ?
C019 C01E . 1.387(2) ?
C019 C00Y . 1.3926(19) ?
C00A C00Y . 1.3915(17) ?
C00A C00O . 1.3984(16) ?
C00A P001 . 1.8042(12) ?
C01A C00V . 1.391(2) ?
C00B C00C . 1.3971(16) ?
C00B C00P . 1.3988(16) ?
C00B P001 . 1.7976(12) ?
C00C C00I . 1.3925(17) ?
C01C C01D . 1.381(2) ?
C00D C00V . 1.3922(18) ?
C00D C00F . 1.3958(17) ?
C01D C00X . 1.396(2) ?
C01E C00Z . 1.387(2) ?
C00F P001 . 1.7975(12) ?
C00G C00M . 1.3951(17) ?
C00G C00U . 1.3954(17) ?
C00G P002 . 1.7969(12) ?
C00H C00X . 1.3947(18) ?
C00H C00K . 1.4029(18) ?
C00H P002 . 1.7975(12) ?
C00I C00R . 1.3871(18) ?
C00J C00N . 1.3948(18) ?
C00J P002 . 1.7951(12) ?
C00M C00S . 1.3883(18) ?
C00N C00W . 1.3925(18) ?
C00O C00Z . 1.3880(18) ?
C00P C00Q . 1.3879(17) ?
C00Q C00R . 1.3904(18) ?
C00S C00T . 1.388(2) ?
N1 P001 . 1.5861(10) ?
N1 P002 . 1.5927(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C2 N4 . . 118.2(12) ?
N2 C2 N6 . . 121.9(10) ?
N4 C2 N6 . . 119.9(11) ?
N2 C3 N3 . . 117.1(4) ?
N2 C3 N5 . . 122.0(3) ?
N3 C3 N5 . . 120.9(3) ?
C2 N2 C3 . . 97.9(7) ?
C3 N3 N4 . . 103.7(6) ?
C2 N4 N3 . . 103.0(8) ?
O1 N5 O2 . . 124.7(2) ?
O1 N5 C3 . . 117.7(2) ?
O2 N5 C3 . . 117.6(2) ?
O4 N6 O3 . . 125.7(4) ?
O4 N6 C2 . . 118.3(7) ?
O3 N6 C2 . . 116.0(8) ?
N5A C1A N4A . . 118.8(12) ?
N5A C1A N1A . . 124.7(9) ?
N4A C1A N1A . . 116.4(10) ?
N5A C1A C2A . . 45.1(13) ?
N4A C1A C2A . . 73.8(13) ?
N1A C1A C2A . . 169.8(13) ?
N4B C2A N6A . . 124.(3) ?
N4B C2A N5A . . 117.(3) ?
N6A C2A N5A . . 119.(3) ?
N4B C2A C1A . . 76.(2) ?
N6A C2A C1A . . 160.(3) ?
N5A C2A C1A . . 40.7(10) ?
N2A N1A C1A . . 114.1(8) ?
N3A N2A N1A . . 170.4(9) ?
C1A N4A N4B . . 105.5(18) ?
C1A N5A C2A . . 94.2(16) ?
O2A N6A O1A . . 114.1(15) ?
O2A N6A C2A . . 125.(2) ?
O1A N6A C2A . . 121.(2) ?
C2A N4B N4A . . 104.(2) ?
C018 C010 C00F . . 119.94(12) ?
C01C C012 C00K . . 119.84(14) ?
C00T C013 C00U . . 119.71(12) ?
C01B C015 C00J . . 119.39(13) ?
C00W C017 C01B . . 120.34(13) ?
C01A C018 C010 . . 120.12(12) ?
C01E C019 C00Y . . 120.01(13) ?
C00Y C00A C00O . . 119.36(11) ?
C00Y C00A P001 . . 123.40(9) ?
C00O C00A P001 . . 117.20(9) ?
C018 C01A C00V . . 120.22(12) ?
C00C C00B C00P . . 119.83(11) ?
C00C C00B P001 . . 120.09(9) ?
C00P C00B P001 . . 120.07(9) ?
C017 C01B C015 . . 120.38(14) ?
C00I C00C C00B . . 119.68(11) ?
C01D C01C C012 . . 120.40(13) ?
C00V C00D C00F . . 119.78(12) ?
C01C C01D C00X . . 120.46(14) ?
C019 C01E C00Z . . 120.27(13) ?
C00D C00F C010 . . 119.83(11) ?
C00D C00F P001 . . 119.59(9) ?
C010 C00F P001 . . 120.51(9) ?
C00M C00G C00U . . 120.05(11) ?
C00M C00G P002 . . 119.81(9) ?
C00U C00G P002 . . 120.13(9) ?
C00X C00H C00K . . 119.59(12) ?
C00X C00H P002 . . 122.22(10) ?
C00K C00H P002 . . 118.07(9) ?
C00R C00I C00C . . 120.23(11) ?
C00N C00J C015 . . 120.10(12) ?
C00N C00J P002 . . 120.43(10) ?
C015 C00J P002 . . 119.44(10) ?
C012 C00K C00H . . 120.24(13) ?
C00S C00M C00G . . 119.71(12) ?
C00W C00N C00J . . 119.77(13) ?
C00Z C00O C00A . . 120.37(12) ?
C00Q C00P C00B . . 119.96(11) ?
C00P C00Q C00R . . 120.04(12) ?
C00I C00R C00Q . . 120.19(11) ?
C00M C00S C00T . . 120.17(12) ?
C00S C00T C013 . . 120.39(12) ?
C013 C00U C00G . . 119.87(12) ?
C01A C00V C00D . . 120.09(13) ?
C017 C00W C00N . . 120.01(13) ?
C00H C00X C01D . . 119.46(14) ?
C00A C00Y C019 . . 120.16(12) ?
C01E C00Z C00O . . 119.83(12) ?
P001 N1 P002 . . 133.27(7) ?
N1 P001 C00F . . 108.68(5) ?
N1 P001 C00B . . 112.93(5) ?
C00F P001 C00B . . 106.74(5) ?
N1 P001 C00A . . 113.75(5) ?
C00F P001 C00A . . 106.42(5) ?
C00B P001 C00A . . 107.91(5) ?
N1 P002 C00J . . 110.95(6) ?
N1 P002 C00G . . 109.48(5) ?
C00J P002 C00G . . 107.45(6) ?
N1 P002 C00H . . 114.76(5) ?
C00J P002 C00H . . 108.26(6) ?
C00G P002 C00H . . 105.58(6) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
