# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shrv441
_database_code_depnum_ccdc_archive 'CCDC 1891124'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H N9 O7, 1.186(H4 N O), 0.814(H4 N)'
_chemical_formula_sum            'C5 H9 N11 O8.19'
_chemical_formula_weight         354.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   4.4903(5)
_cell_length_b                   9.9764(10)
_cell_length_c                   14.3321(14)
_cell_angle_alpha                78.415(3)
_cell_angle_beta                 82.415(3)
_cell_angle_gamma                87.929(3)
_cell_volume                     623.42(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1465
_cell_measurement_theta_min      3.236
_cell_measurement_theta_max      25.133

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_F_000             363
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6485
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5428
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.773
_diffrn_reflns_theta_max         25.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2271
_reflns_number_gt                1376
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Significant disorder observed in cation channels.  Mixed occupancy of one cation is observed (NH4:HONH3 = 82:18).  Hydrogen atoms in cations could not be located and have been fixed using DFIX and DANG commands to set ideal bond lengths and angles.

One of the nitro groups is disordered over two positions and has been modeled with a 85:15 ratio.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²+0.0902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2271
_refine_ls_number_parameters     257
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.005
_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
O1 O 0.2877(6) 0.0584(2) 0.08278(16) 0.0374(7) Uani 1 1 d . . . . .
O2 O -0.0809(6) 0.0041(3) 0.19793(18) 0.0472(9) Uani 1 1 d . . . . .
N3 N 0.1189(7) 0.0882(3) 0.1522(2) 0.0343(8) Uani 1 1 d . . . . .
N4 N 0.1330(7) 0.2011(3) 0.1847(2) 0.0361(9) Uani 1 1 d . . . . .
C5 C 0.3547(8) 0.2925(3) 0.1383(2) 0.0267(9) Uani 1 1 d . . . . .
N6 N 0.5567(7) 0.2876(3) 0.0638(2) 0.0316(8) Uani 1 1 d . . . . .
O7 O 0.7224(6) 0.4065(2) 0.05108(17) 0.0345(7) Uani 1 1 d . . . . .
N8 N 0.6175(7) 0.4831(3) 0.1183(2) 0.0293(8) Uani 1 1 d . . . . .
C9 C 0.3914(8) 0.4161(3) 0.1717(2) 0.0265(9) Uani 1 1 d . . . . .
C10 C 0.2194(8) 0.4717(3) 0.2497(2) 0.0232(8) Uani 1 1 d . . . . .
N11 N -0.0100(7) 0.4074(3) 0.3065(2) 0.0262(7) Uani 1 1 d . . . . .
N12 N -0.0987(6) 0.4961(3) 0.36467(18) 0.0235(7) Uani 1 1 d . . . . .
H12 H -0.2503 0.4827 0.4110 0.028 Uiso 1 1 calc R U . . .
C13 C 0.0762(8) 0.6080(3) 0.3423(2) 0.0221(8) Uani 1 1 d . . . . .
N14 N 0.2832(6) 0.5955(3) 0.26834(19) 0.0240(7) Uani 1 1 d . . . . .
C15 C 0.0435(7) 0.7200(3) 0.3942(2) 0.0208(8) Uani 1 1 d . . . . .
N16 N -0.1810(7) 0.7215(3) 0.4691(2) 0.0276(8) Uani 1 1 d . . . . .
O17 O -0.3650(5) 0.6231(2) 0.48998(16) 0.0296(7) Uani 1 1 d . . . . .
O18 O -0.2084(7) 0.8136(3) 0.5159(2) 0.0544(9) Uani 1 1 d . . . . .
N19 N 0.2477(7) 0.8294(3) 0.36947(19) 0.0263(7) Uani 1 1 d . . . . .
O20A O 0.218(2) 0.9280(8) 0.4114(4) 0.045(2) Uani 0.85(2) 1 d . . P A 1
O21A O 0.4601(19) 0.8258(6) 0.3058(4) 0.0326(16) Uani 0.85(2) 1 d . . P A 1
O20B O 0.333(9) 0.885(4) 0.432(2) 0.045(2) Uani 0.15(2) 1 d . . P A 2
O21B O 0.356(9) 0.854(4) 0.288(2) 0.0326(16) Uani 0.15(2) 1 d . . P A 2
N22A N 0.7300(12) 0.1325(10) 0.3796(4) 0.0337(10) Uani 0.186(10) 1 d D . P B 1
H22E H 0.8969 0.1833 0.3552 0.051 Uiso 0.186(10) 1 calc R U P B 1
H22F H 0.7847 0.0435 0.3990 0.051 Uiso 0.186(10) 1 calc R U P B 1
H22G H 0.6323 0.1646 0.4306 0.051 Uiso 0.186(10) 1 calc R U P B 1
O23 O 0.520(4) 0.1426(11) 0.3014(12) 0.053(7) Uani 0.186(10) 1 d D . P B 1
H23 H 0.4870(12) 0.2252(9) 0.2959(4) 0.079 Uiso 0.186(10) 1 d D U P B 1
N22B N 0.7336(10) 0.1207(4) 0.3628(3) 0.0337(10) Uani 0.814(10) 1 d D . P B 2
H22A H 0.715(5) 0.0708(17) 0.3173(10) 0.051 Uiso 0.814(10) 1 d D U P B 2
H22B H 0.548(2) 0.144(3) 0.389(2) 0.051 Uiso 0.814(10) 1 d D U P B 2
H22C H 0.893(4) 0.089(2) 0.3940(14) 0.051 Uiso 0.814(10) 1 d D U P B 2
H22D H 0.763(6) 0.2101(7) 0.3342(13) 0.051 Uiso 0.814(10) 1 d D U P B 2
O24 O 0.8898(9) 0.7555(6) 0.1076(3) 0.1176(19) Uani 1 1 d D . . . .
H24 H 1.0042(7) 0.8140(17) 0.1146(15) 0.176 Uiso 1 1 d D U . . .
N25 N 0.6015(5) 0.8000(3) 0.1140(2) 0.0497(11) Uani 1 1 d D . . . .
H25A H 0.4924 0.7475 0.1656 0.075 Uiso 1 1 calc R U . . .
H25B H 0.5235 0.7938 0.0596 0.075 Uiso 1 1 calc R U . . .
H25C H 0.5943 0.8887 0.1211 0.075 Uiso 1 1 calc R U . . .


_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 N3 1.247(3) . ?
O2 N3 1.272(4) . ?
N3 N4 1.309(4) . ?
N4 C5 1.382(4) . ?
C5 N6 1.314(4) . ?
C5 C9 1.432(5) . ?
N6 O7 1.391(4) . ?
O7 N8 1.372(3) . ?
N8 C9 1.305(4) . ?
C9 C10 1.465(4) . ?
C10 N11 1.323(4) . ?
C10 N14 1.363(4) . ?
N11 N12 1.349(3) . ?
N12 C13 1.348(4) . ?
N12 H12 0.8800 . ?
C13 N14 1.337(4) . ?
C13 C15 1.455(4) . ?
C15 N16 1.375(4) . ?
C15 N19 1.410(4) . ?
N16 O18 1.235(3) . ?
N16 O17 1.269(3) . ?
N19 O21B 1.19(3) . ?
N19 O21A 1.235(5) . ?
N19 O20A 1.246(5) . ?
N19 O20B 1.25(3) . ?
N22A O23 1.54(2) . ?
N22A H22E 0.9100 . ?
N22A H22F 0.9100 . ?
N22A H22G 0.9100 . ?
O23 H23 0.821(9) . ?
N22B H22A 0.9099(11) . ?
N22B H22B 0.9099(11) . ?
N22B H22C 0.9100(11) . ?
N22B H22D 0.9100(11) . ?
O24 N25 1.351(5) . ?
O24 H24 0.821(9) . ?
N25 H25A 0.9100 . ?
N25 H25B 0.9100 . ?
N25 H25C 0.9100 . ?

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 N3 O2 119.6(3) . . ?
O1 N3 N4 124.9(3) . . ?
O2 N3 N4 115.4(2) . . ?
N3 N4 C5 116.7(3) . . ?
N6 C5 N4 130.9(3) . . ?
N6 C5 C9 109.1(3) . . ?
N4 C5 C9 120.0(3) . . ?
C5 N6 O7 104.9(2) . . ?
N8 O7 N6 111.1(2) . . ?
C9 N8 O7 106.2(3) . . ?
N8 C9 C5 108.6(3) . . ?
N8 C9 C10 120.7(3) . . ?
C5 C9 C10 130.7(3) . . ?
N11 C10 N14 115.0(3) . . ?
N11 C10 C9 123.1(3) . . ?
N14 C10 C9 121.9(3) . . ?
C10 N11 N12 102.2(3) . . ?
C13 N12 N11 110.9(2) . . ?
C13 N12 H12 124.5 . . ?
N11 N12 H12 124.5 . . ?
N14 C13 N12 109.0(3) . . ?
N14 C13 C15 127.0(3) . . ?
N12 C13 C15 124.1(3) . . ?
C13 N14 C10 102.9(3) . . ?
N16 C15 N19 118.2(3) . . ?
N16 C15 C13 121.5(3) . . ?
N19 C15 C13 120.3(3) . . ?
O18 N16 O17 119.8(3) . . ?
O18 N16 C15 122.7(3) . . ?
O17 N16 C15 117.6(2) . . ?
O21A N19 O20A 120.1(3) . . ?
O21B N19 O20B 123(2) . . ?
O21B N19 C15 115.4(16) . . ?
O21A N19 C15 118.9(3) . . ?
O20A N19 C15 121.0(3) . . ?
O20B N19 C15 121.4(13) . . ?
O23 N22A H22E 109.5 . . ?
O23 N22A H22F 109.5 . . ?
H22E N22A H22F 109.5 . . ?
O23 N22A H22G 109.5 . . ?
H22E N22A H22G 109.5 . . ?
H22F N22A H22G 109.5 . . ?
N22A O23 H23 95.7(15) . . ?
H22A N22B H22B 109.49(18) . . ?
H22A N22B H22C 109.48(18) . . ?
H22B N22B H22C 128(2) . . ?
H22A N22B H22D 109.48(18) . . ?
H22B N22B H22D 89(3) . . ?
H22C N22B H22D 109.48(18) . . ?
N25 O24 H24 111.5(8) . . ?
O24 N25 H25A 109.5 . . ?
O24 N25 H25B 109.5 . . ?
H25A N25 H25B 109.5 . . ?
O24 N25 H25C 109.5 . . ?
H25A N25 H25C 109.5 . . ?
H25B N25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 N4 C5 -0.6(6) . . . . ?
O2 N3 N4 C5 178.0(3) . . . . ?
N3 N4 C5 N6 1.5(6) . . . . ?
N3 N4 C5 C9 -177.8(4) . . . . ?
N4 C5 N6 O7 -178.7(4) . . . . ?
C9 C5 N6 O7 0.7(4) . . . . ?
C5 N6 O7 N8 -0.2(4) . . . . ?
N6 O7 N8 C9 -0.4(4) . . . . ?
O7 N8 C9 C5 0.9(4) . . . . ?
O7 N8 C9 C10 -178.2(3) . . . . ?
N6 C5 C9 N8 -1.1(5) . . . . ?
N4 C5 C9 N8 178.4(3) . . . . ?
N6 C5 C9 C10 177.8(4) . . . . ?
N4 C5 C9 C10 -2.7(7) . . . . ?
N8 C9 C10 N11 -179.4(4) . . . . ?
C5 C9 C10 N11 1.8(6) . . . . ?
N8 C9 C10 N14 1.4(6) . . . . ?
C5 C9 C10 N14 -177.4(4) . . . . ?
N14 C10 N11 N12 0.3(4) . . . . ?
C9 C10 N11 N12 -179.0(3) . . . . ?
C10 N11 N12 C13 -0.4(4) . . . . ?
N11 N12 C13 N14 0.3(4) . . . . ?
N11 N12 C13 C15 -177.9(3) . . . . ?
N12 C13 N14 C10 -0.2(4) . . . . ?
C15 C13 N14 C10 178.0(4) . . . . ?
N11 C10 N14 C13 -0.1(4) . . . . ?
C9 C10 N14 C13 179.2(3) . . . . ?
N14 C13 C15 N16 179.6(3) . . . . ?
N12 C13 C15 N16 -2.5(6) . . . . ?
N14 C13 C15 N19 -1.7(6) . . . . ?
N12 C13 C15 N19 176.2(3) . . . . ?
N19 C15 N16 O18 -0.7(5) . . . . ?
C13 C15 N16 O18 178.0(4) . . . . ?
N19 C15 N16 O17 179.3(3) . . . . ?
C13 C15 N16 O17 -2.0(5) . . . . ?
N16 C15 N19 O21B -152(2) . . . . ?
C13 C15 N19 O21B 29(2) . . . . ?
N16 C15 N19 O21A 176.1(6) . . . . ?
C13 C15 N19 O21A -2.6(7) . . . . ?
N16 C15 N19 O20A -3.3(8) . . . . ?
C13 C15 N19 O20A 178.0(7) . . . . ?
N16 C15 N19 O20B 36(3) . . . . ?
C13 C15 N19 O20B -143(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12 O17 0.88 1.98 2.550(3) 120.8 .
N12 H12 O17 0.88 2.23 3.073(3) 159.0 2_466
N22A H22E N4 0.91 2.51 3.088(6) 122.0 1_655
N22A H22E N11 0.91 2.24 2.956(10) 135.0 1_655
N22A H22F O18 0.91 2.56 3.405(9) 155.5 1_645
N22A H22F O20A 0.91 2.23 2.956(13) 135.9 1_645
N22A H22G N16 0.91 2.68 3.535(8) 156.8 2_566
N22A H22G O18 0.91 1.98 2.706(7) 135.9 2_566
N22A H22G O20A 0.91 2.44 2.973(9) 117.7 2_666
N22B H22A O2 0.9099(11) 2.051(13) 2.853(5) 146.3(18) 1_655
N22B H22B O18 0.9099(11) 2.000(10) 2.877(5) 161(2) 2_566
N22B H22C O18 0.9100(11) 2.388(17) 3.088(5) 133.8(17) 2_666
N22B H22D N11 0.9100(11) 2.191(11) 3.038(5) 155(2) 1_655
O24 H24 O2 0.821(9) 2.430(14) 3.034(6) 131.2(9) 1_665
N25 H25A N14 0.91 2.05 2.943(4) 167.8 .
N25 H25A O21A 0.91 2.28 2.800(5) 115.6 .
N25 H25A O21B 0.91 2.23 2.73(3) 114.1 .
N25 H25B O1 0.91 2.34 2.877(4) 117.5 2_665
N25 H25B N6 0.91 2.16 3.030(4) 158.8 2_665
N25 H25C O1 0.91 2.17 2.876(4) 133.5 1_565
N25 H25C O2 0.91 2.39 3.046(4) 128.8 1_665

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.067


# start Validation Reply Form
_vrf_PLAT430_shrv441             
;
PROBLEM: Short Inter D...A Contact  O18    ..  O20B    ..       2.53 Ang.  
RESPONSE: High density energetic materials often display close contacts.
;
# 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_shrv460
_database_code_depnum_ccdc_archive 'CCDC 1891126'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shrv460             
;
PROBLEM: Short Inter D...A Contact  O36      ..O74      .       2.77 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
_vrf_PLAT430_shrv460_2           
;
PROBLEM: Short Inter D...A Contact  O42      ..O32B     .       2.80 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
_vrf_PLAT430_shrv460_3           
;
PROBLEM: Short Inter D...A Contact  O72      ..N111     .       2.86 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
_vrf_PLAT430_shrv460_4           
;
PROBLEM: Short Inter D...A Contact  O73      ..O6B      .       2.73 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
_vrf_PLAT430_shrv460_5           
;
PROBLEM: Short Inter D...A Contact  O110     ..N55      .       2.86 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Friday 08 February 2019 07:12 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 N16 O10, 0.25(C2 H3 N)'
_chemical_formula_sum            'C10.50 H4.75 N16.25 O10'
_chemical_formula_weight         518.56

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   21.7441(5)
_cell_length_b                   9.4048(2)
_cell_length_c                   39.3917(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.7490(10)
_cell_angle_gamma                90
_cell_volume                     7790.1(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.231
_cell_measurement_theta_max      29.346

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             4184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            90206
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         0.980
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             22003
_reflns_number_gt                13545
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_refine_special_details          
;
Disorder in nitro groups has been modelled in three instances. Thermal 
parameters for these atoms have been restrained to approximate isotropic
behavior.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0750P)²+3.2716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         22003
_refine_ls_number_parameters     1390
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.005
_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
O1 O 0.85436(18) 0.6045(3) 0.92267(8) 0.1150(14) Uani 1 1 d . . . . .
O2 O 0.82639(11) 0.7389(2) 0.96016(6) 0.0598(6) Uani 1 1 d . . . . .
N3 N 0.82564(11) 0.6281(2) 0.94418(6) 0.0419(5) Uani 1 1 d . . . . .
C4 C 0.79294(9) 0.5039(2) 0.95679(5) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.8111 0.4936 0.9827 0.026 Uiso 1 1 calc R U . . .
N5 N 0.72400(10) 0.5475(2) 0.95041(6) 0.0388(5) Uani 1 1 d . . . . .
O6 O 0.68540(16) 0.5096(7) 0.92508(10) 0.0578(19) Uani 0.724(11) 1 d . . P A 1
O6B O 0.7101(6) 0.5994(14) 0.9145(2) 0.058(4) Uani 0.276(11) 1 d . U P A 2
O7 O 0.70923(10) 0.6061(2) 0.97430(6) 0.0544(6) Uani 1 1 d . . . . .
C8 C 0.80325(9) 0.3687(2) 0.93976(5) 0.0180(4) Uani 1 1 d . . . . .
N9 N 0.77452(8) 0.33425(18) 0.90700(4) 0.0198(4) Uani 1 1 d . . . . .
N10 N 0.80087(8) 0.20688(17) 0.90362(4) 0.0172(3) Uani 1 1 d . . . . .
H10 H 0.7912 0.1541 0.8846 0.021 Uiso 1 1 calc R U . . .
C11 C 0.84359(9) 0.1722(2) 0.93323(5) 0.0161(4) Uani 1 1 d . . . . .
N12 N 0.84641(8) 0.27357(18) 0.95726(4) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.88447(9) 0.0473(2) 0.93990(5) 0.0172(4) Uani 1 1 d . . . . .
N14 N 0.91969(8) 0.03013(19) 0.97190(4) 0.0243(4) Uani 1 1 d . . . . .
O15 O 0.95655(7) -0.08782(17) 0.97094(4) 0.0293(4) Uani 1 1 d . . . . .
N16 N 0.94419(9) -0.1446(2) 0.93822(5) 0.0274(4) Uani 1 1 d . . . . .
C17 C 0.89931(9) -0.0645(2) 0.91870(5) 0.0204(4) Uani 1 1 d . . . . .
N18 N 0.87737(8) -0.10756(19) 0.88343(4) 0.0230(4) Uani 1 1 d . . . . .
N19 N 0.82894(7) -0.04000(17) 0.86710(4) 0.0152(3) Uani 1 1 d . . . . .
C20 C 0.80637(9) -0.0896(2) 0.83201(5) 0.0171(4) Uani 1 1 d . . . . .
N21 N 0.82866(9) -0.2024(2) 0.81982(5) 0.0261(4) Uani 1 1 d . . . . .
O22 O 0.79388(8) -0.21254(18) 0.78571(4) 0.0333(4) Uani 1 1 d . . . . .
N23 N 0.74961(9) -0.1049(2) 0.77685(5) 0.0278(4) Uani 1 1 d . . . . .
C24 C 0.75654(9) -0.0290(2) 0.80518(5) 0.0182(4) Uani 1 1 d . . . . .
C25 C 0.71754(9) 0.0961(2) 0.80603(5) 0.0161(4) Uani 1 1 d . . . . .
N26 N 0.67222(7) 0.14374(17) 0.77878(4) 0.0164(3) Uani 1 1 d . . . . .
H26 H 0.6613 0.1034 0.7579 0.020 Uiso 1 1 calc R U . . .
N27 N 0.64560(8) 0.26259(18) 0.78785(4) 0.0192(3) Uani 1 1 d . . . . .
C28 C 0.67701(9) 0.2795(2) 0.82094(5) 0.0181(4) Uani 1 1 d . . . . .
N29 N 0.72201(8) 0.17936(18) 0.83375(4) 0.0180(3) Uani 1 1 d . . . . .
C30 C 0.66487(10) 0.4005(2) 0.84258(6) 0.0249(5) Uani 1 1 d . . . . .
H30 H 0.6732 0.3688 0.8676 0.030 Uiso 1 1 calc R U . B 1
N31 N 0.59732(12) 0.4490(3) 0.83044(7) 0.0328(6) Uani 0.862(4) 1 d D . P C 1
O32 O 0.58326(13) 0.5317(3) 0.80626(6) 0.0510(8) Uani 0.862(4) 1 d D . P C 1
O33 O 0.56057(15) 0.3937(4) 0.84532(8) 0.0553(8) Uani 0.862(4) 1 d D . P C 1
N34 N 0.70720(16) 0.5265(3) 0.84072(9) 0.0457(8) Uani 0.862(4) 1 d D . P C 1
O35 O 0.74909(16) 0.5113(3) 0.82612(9) 0.0607(9) Uani 0.862(4) 1 d D . P C 1
O36 O 0.69748(16) 0.6321(3) 0.85592(9) 0.0890(12) Uani 0.862(4) 1 d D . P C 1
N31B N 0.5958(9) 0.399(2) 0.8474(5) 0.045(5) Uani 0.138(4) 1 d D U P C 2
O32B O 0.5518(8) 0.362(3) 0.8241(6) 0.092(7) Uani 0.138(4) 1 d D U P C 2
O33B O 0.5906(7) 0.4440(19) 0.8750(4) 0.064(5) Uani 0.138(4) 1 d D U P C 2
N34B N 0.6655(10) 0.540(2) 0.8226(6) 0.066(6) Uani 0.138(4) 1 d D U P C 2
O35B O 0.7173(10) 0.567(2) 0.8203(6) 0.059(5) Uani 0.138(4) 1 d D U P C 2
O36B O 0.6171(12) 0.601(3) 0.8096(9) 0.129(11) Uani 0.138(4) 1 d D U P C 2
O37 O 0.51023(9) 0.62417(18) 0.72769(5) 0.0405(4) Uani 1 1 d . . . . .
O38 O 0.58629(10) 0.5353(2) 0.70822(6) 0.0605(6) Uani 1 1 d . . . . .
N39 N 0.54098(10) 0.5263(2) 0.72046(5) 0.0297(4) Uani 1 1 d . . . . .
C40 C 0.52364(10) 0.3772(2) 0.72912(5) 0.0209(4) Uani 1 1 d . . . . .
H40 H 0.5524 0.3501 0.7523 0.025 Uiso 1 1 calc R U . . .
N41 N 0.45694(11) 0.3839(2) 0.73326(7) 0.0402(5) Uani 1 1 d . . . . .
O42 O 0.45195(13) 0.3706(2) 0.76318(7) 0.0757(8) Uani 1 1 d . . . . .
O43 O 0.41433(9) 0.3998(2) 0.70723(7) 0.0592(6) Uani 1 1 d . . . . .
C44 C 0.53181(9) 0.2706(2) 0.70286(5) 0.0166(4) Uani 1 1 d . . . . .
N45 N 0.50335(8) 0.27889(18) 0.66891(4) 0.0191(3) Uani 1 1 d . . . . .
N46 N 0.52497(7) 0.16121(17) 0.65613(4) 0.0164(3) Uani 1 1 d . . . . .
H46 H 0.5147 0.1353 0.6339 0.020 Uiso 1 1 calc R U . . .
C47 C 0.56420(8) 0.0898(2) 0.68210(5) 0.0140(4) Uani 1 1 d . . . . .
N48 N 0.56973(7) 0.15589(17) 0.71267(4) 0.0157(3) Uani 1 1 d . . . . .
C49 C 0.59934(9) -0.0398(2) 0.67959(5) 0.0164(4) Uani 1 1 d . . . . .
N50 N 0.63931(8) -0.08281(19) 0.70835(4) 0.0229(4) Uani 1 1 d . . . . .
O51 O 0.66623(7) -0.20620(17) 0.69979(4) 0.0287(4) Uani 1 1 d . . . . .
N52 N 0.64228(8) -0.23964(19) 0.66533(5) 0.0248(4) Uani 1 1 d . . . . .
C53 C 0.60175(9) -0.1388(2) 0.65225(5) 0.0177(4) Uani 1 1 d . . . . .
N54 N 0.57170(8) -0.15326(18) 0.61636(4) 0.0190(3) Uani 1 1 d . . . . .
N55 N 0.53613(7) -0.05027(17) 0.60412(4) 0.0163(3) Uani 1 1 d . . . . .
C56 C 0.50423(9) -0.0714(2) 0.56820(5) 0.0169(4) Uani 1 1 d . . . . .
N57 N 0.51004(9) -0.1837(2) 0.54972(4) 0.0247(4) Uani 1 1 d . . . . .
O58 O 0.47044(7) -0.15972(17) 0.51716(4) 0.0283(4) Uani 1 1 d . . . . .
N59 N 0.43912(8) -0.03072(19) 0.51572(4) 0.0237(4) Uani 1 1 d . . . . .
C60 C 0.45990(9) 0.0250(2) 0.54703(5) 0.0159(4) Uani 1 1 d . . . . .
C61 C 0.43663(9) 0.1606(2) 0.55605(5) 0.0149(4) Uani 1 1 d . . . . .
N62 N 0.40252(8) 0.25185(18) 0.53263(4) 0.0188(3) Uani 1 1 d . . . . .
H62 H 0.3933 0.2409 0.5097 0.023 Uiso 1 1 calc R U . . .
N63 N 0.38437(8) 0.36284(18) 0.54930(4) 0.0208(4) Uani 1 1 d . . . . .
C64 C 0.40943(9) 0.3308(2) 0.58263(5) 0.0164(4) Uani 1 1 d . . . . .
N65 N 0.44262(7) 0.20750(17) 0.58852(4) 0.0151(3) Uani 1 1 d . . . . .
C66 C 0.39952(9) 0.4220(2) 0.61181(5) 0.0203(4) Uani 1 1 d . . . . .
H66 H 0.3976 0.3606 0.6322 0.024 Uiso 1 1 calc R U . . .
N67 N 0.33778(9) 0.5023(2) 0.59956(5) 0.0306(4) Uani 1 1 d . . . . .
O68 O 0.33963(9) 0.6228(2) 0.58830(5) 0.0437(5) Uani 1 1 d . . . . .
O69 O 0.29044(9) 0.4378(2) 0.60070(6) 0.0490(5) Uani 1 1 d . . . . .
N70 N 0.45065(10) 0.5338(2) 0.62368(5) 0.0312(4) Uani 1 1 d . . . . .
O71 O 0.49042(9) 0.5466(2) 0.60761(6) 0.0510(5) Uani 1 1 d . . . . .
O72 O 0.44739(10) 0.60154(19) 0.64953(5) 0.0460(5) Uani 1 1 d . . . . .
O73 O 0.71128(10) 0.8901(3) 0.91449(6) 0.0785(8) Uani 1 1 d . . . . .
O74 O 0.67583(11) 0.9218(3) 0.85927(6) 0.0639(6) Uani 1 1 d . . . . .
N75 N 0.66909(10) 0.9108(2) 0.88867(6) 0.0367(5) Uani 1 1 d . . . . .
C76 C 0.60159(10) 0.9244(2) 0.89178(5) 0.0223(4) Uani 1 1 d . . . . .
H76 H 0.5721 0.8947 0.8690 0.027 Uiso 1 1 calc R U . . .
N77 N 0.59075(11) 1.0794(2) 0.89764(5) 0.0351(5) Uani 1 1 d . . . . .
O78 O 0.63626(12) 1.1597(2) 0.90229(7) 0.0669(7) Uani 1 1 d . . . . .
O79 O 0.53647(11) 1.1092(2) 0.89668(6) 0.0620(6) Uani 1 1 d . . . . .
C80 C 0.58924(9) 0.8337(2) 0.92021(5) 0.0175(4) Uani 1 1 d . . . . .
N81 N 0.60622(8) 0.87044(19) 0.95373(4) 0.0213(4) Uani 1 1 d . . . . .
N82 N 0.58897(8) 0.75559(18) 0.96939(4) 0.0185(3) Uani 1 1 d . . . . .
H82 H 0.5936 0.7464 0.9921 0.022 Uiso 1 1 calc R U . . .
C83 C 0.56365(9) 0.6572(2) 0.94536(5) 0.0158(4) Uani 1 1 d . . . . .
N84 N 0.56186(7) 0.70376(17) 0.91331(4) 0.0164(3) Uani 1 1 d . . . . .
C85 C 0.54353(9) 0.5171(2) 0.95376(5) 0.0171(4) Uani 1 1 d . . . . .
N86 N 0.56410(9) 0.4616(2) 0.98510(4) 0.0250(4) Uani 1 1 d . . . . .
O87 O 0.53527(8) 0.32947(17) 0.98300(4) 0.0309(4) Uani 1 1 d . . . . .
N88 N 0.49744(9) 0.3038(2) 0.95003(4) 0.0265(4) Uani 1 1 d . . . . .
C89 C 0.50201(9) 0.4186(2) 0.93198(5) 0.0175(4) Uani 1 1 d . . . . .
N90 N 0.46936(7) 0.44162(18) 0.89631(4) 0.0163(3) Uani 1 1 d . . . . .
N91 N 0.43037(8) 0.34427(18) 0.88446(4) 0.0189(3) Uani 1 1 d . . . . .
C92 C 0.39553(9) 0.3675(2) 0.84949(5) 0.0169(4) Uani 1 1 d . . . . .
N93 N 0.35085(8) 0.27359(19) 0.83730(4) 0.0232(4) Uani 1 1 d . . . . .
O94 O 0.32106(7) 0.31841(16) 0.80441(4) 0.0258(3) Uani 1 1 d . . . . .
N95 N 0.34740(8) 0.44216(19) 0.79594(4) 0.0211(4) Uani 1 1 d . . . . .
C96 C 0.39389(9) 0.4739(2) 0.82324(5) 0.0158(4) Uani 1 1 d . . . . .
C97 C 0.43145(9) 0.5992(2) 0.81985(5) 0.0139(4) Uani 1 1 d . . . . .
N98 N 0.47616(7) 0.66313(17) 0.84470(4) 0.0165(3) Uani 1 1 d . . . . .
H98 H 0.4891 0.6347 0.8666 0.020 Uiso 1 1 calc R U . . .
N99 N 0.49846(8) 0.77795(18) 0.83113(4) 0.0187(3) Uani 1 1 d . . . . .
C100 C 0.46529(9) 0.7749(2) 0.79794(5) 0.0163(4) Uani 1 1 d . . . . .
N101 N 0.42328(7) 0.66664(17) 0.78939(4) 0.0158(3) Uani 1 1 d . . . . .
C102 C 0.47369(10) 0.8825(2) 0.77181(5) 0.0198(4) Uani 1 1 d . . . . .
H102 H 0.4716 0.8346 0.7489 0.024 Uiso 1 1 calc R U . . .
N103 N 0.53799(10) 0.9527(2) 0.78504(5) 0.0305(4) Uani 1 1 d . . . . .
O104 O 0.58208(9) 0.8927(2) 0.77759(5) 0.0464(5) Uani 1 1 d . . . . .
O105 O 0.54076(10) 1.0592(2) 0.80295(5) 0.0489(5) Uani 1 1 d . . . . .
N106 N 0.42438(10) 0.9999(2) 0.76634(5) 0.0298(4) Uani 1 1 d . . . . .
O107 O 0.42373(10) 1.07905(19) 0.74167(5) 0.0462(5) Uani 1 1 d . . . . .
O108 O 0.38963(10) 1.0055(2) 0.78566(5) 0.0490(5) Uani 1 1 d . . . . .
O109 O 0.45505(7) 0.89045(18) 0.68114(5) 0.0351(4) Uani 1 1 d . . . . .
O110 O 0.42074(9) 0.9017(2) 0.62434(5) 0.0440(5) Uani 1 1 d . . . . .
N111 N 0.41324(9) 0.89332(19) 0.65386(5) 0.0257(4) Uani 1 1 d . . . . .
C112 C 0.34512(9) 0.8870(2) 0.65611(5) 0.0180(4) Uani 1 1 d . . . . .
H112 H 0.3180 0.8695 0.6319 0.022 Uiso 1 1 calc R U . . .
N113 N 0.32880(9) 1.0343(2) 0.66715(5) 0.0287(4) Uani 1 1 d . . . . .
O114 O 0.27927(10) 1.0409(2) 0.67567(6) 0.0562(6) Uani 1 1 d . . . . .
O115 O 0.36318(9) 1.13233(17) 0.66434(5) 0.0391(4) Uani 1 1 d . . . . .
C116 C 0.33164(9) 0.7721(2) 0.67895(5) 0.0163(4) Uani 1 1 d . . . . .
N117 N 0.35867(8) 0.76281(18) 0.71296(4) 0.0196(4) Uani 1 1 d . . . . .
N118 N 0.33149(8) 0.64408(17) 0.72199(4) 0.0179(3) Uani 1 1 d . . . . .
H118 H 0.3395 0.6086 0.7433 0.021 Uiso 1 1 calc R U . . .
C119 C 0.29070(8) 0.5883(2) 0.69386(5) 0.0146(4) Uani 1 1 d . . . . .
N120 N 0.28917(7) 0.66714(17) 0.66555(4) 0.0152(3) Uani 1 1 d . . . . .
C121 C 0.25321(9) 0.4603(2) 0.69431(5) 0.0173(4) Uani 1 1 d . . . . .
N122 N 0.26388(9) 0.37727(19) 0.72170(4) 0.0246(4) Uani 1 1 d . . . . .
O123 O 0.22012(7) 0.26861(16) 0.71252(4) 0.0278(4) Uani 1 1 d . . . . .
N124 N 0.18228(8) 0.28541(19) 0.67939(4) 0.0224(4) Uani 1 1 d . . . . .
C125 C 0.20144(9) 0.4036(2) 0.66804(5) 0.0165(4) Uani 1 1 d . . . . .
N126 N 0.17492(7) 0.46031(17) 0.63400(4) 0.0150(3) Uani 1 1 d . . . . .
N127 N 0.12185(8) 0.40465(19) 0.61995(4) 0.0207(4) Uani 1 1 d . . . . .
C128 C 0.09678(9) 0.4494(2) 0.58507(5) 0.0173(4) Uani 1 1 d . . . . .
N129 N 0.04939(8) 0.3735(2) 0.56668(5) 0.0243(4) Uani 1 1 d . . . . .
O130 O 0.03654(7) 0.42683(17) 0.53354(4) 0.0271(3) Uani 1 1 d . . . . .
N131 N 0.07562(8) 0.53994(19) 0.53134(4) 0.0228(4) Uani 1 1 d . . . . .
C132 C 0.11281(9) 0.5557(2) 0.56274(5) 0.0160(4) Uani 1 1 d . . . . .
C133 C 0.15498(9) 0.6786(2) 0.56847(5) 0.0143(4) Uani 1 1 d . . . . .
N134 N 0.20138(7) 0.70837(17) 0.59702(4) 0.0147(3) Uani 1 1 d . . . . .
H134 H 0.2134 0.6527 0.6155 0.018 Uiso 1 1 calc R U . . .
N135 N 0.22701(7) 0.83564(17) 0.59342(4) 0.0170(3) Uani 1 1 d . . . . .
C136 C 0.19407(9) 0.8757(2) 0.56187(5) 0.0160(4) Uani 1 1 d . . . . .
N137 N 0.14898(7) 0.78358(17) 0.54497(4) 0.0168(3) Uani 1 1 d . . . . .
C138 C 0.20385(9) 1.0187(2) 0.54799(5) 0.0191(4) Uani 1 1 d . . . . .
H138 H 0.1908 1.0176 0.5218 0.023 Uiso 1 1 calc R U . . .
N139 N 0.27341(9) 1.0578(2) 0.56068(5) 0.0248(4) Uani 1 1 d . . . . .
O140 O 0.30728(8) 1.0123(2) 0.54299(5) 0.0440(5) Uani 1 1 d . . . . .
O141 O 0.29078(9) 1.1229(2) 0.58781(5) 0.0445(5) Uani 1 1 d . . . . .
N142 N 0.16671(9) 1.1319(2) 0.56182(5) 0.0290(4) Uani 1 1 d . . . . .
O143 O 0.13177(11) 1.0928(2) 0.57943(6) 0.0592(6) Uani 1 1 d . . . . .
O144 O 0.17288(10) 1.25285(19) 0.55291(6) 0.0508(5) Uani 1 1 d . . . . .
C145 C 0.24589(14) 0.5028(3) 0.50148(8) 0.0551(8) Uani 1 1 d . . . . .
H14A H 0.2914 0.5196 0.5045 0.083 Uiso 1 1 calc R U . . .
H14B H 0.2345 0.5263 0.5233 0.083 Uiso 1 1 calc R U . . .
H14C H 0.2215 0.5627 0.4824 0.083 Uiso 1 1 calc R U . . .
C146 C 0.23158(15) 0.3543(4) 0.49295(8) 0.0487(8) Uani 1 1 d . . . . .
N147 N 0.22144(16) 0.2365(3) 0.48661(8) 0.0700(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
O1 N3 1.195(3) . ?
O2 N3 1.215(3) . ?
N3 C4 1.516(3) . ?
C4 C8 1.481(3) . ?
C4 N5 1.512(3) . ?
C4 H4 1.0000 . ?
N5 O6 1.184(3) . ?
N5 O7 1.202(3) . ?
N5 O6B 1.455(12) . ?
C8 N9 1.323(2) . ?
C8 N12 1.352(2) . ?
N9 N10 1.349(2) . ?
N10 C11 1.333(2) . ?
N10 H10 0.8800 . ?
C11 N12 1.334(2) . ?
C11 C13 1.457(3) . ?
C13 N14 1.308(2) . ?
C13 C17 1.430(3) . ?
N14 O15 1.375(2) . ?
O15 N16 1.357(2) . ?
N16 C17 1.315(3) . ?
C17 N18 1.409(3) . ?
N18 N19 1.258(2) . ?
N19 C20 1.422(2) . ?
C20 N21 1.307(3) . ?
C20 C24 1.426(3) . ?
N21 O22 1.367(2) . ?
O22 N23 1.379(2) . ?
N23 C24 1.301(3) . ?
C24 C25 1.456(3) . ?
C25 N29 1.327(2) . ?
C25 N26 1.336(2) . ?
N26 N27 1.348(2) . ?
N26 H26 0.8800 . ?
N27 C28 1.318(2) . ?
C28 N29 1.359(2) . ?
C28 C30 1.485(3) . ?
C30 N31 1.495(3) . ?
C30 N34 1.514(4) . ?
C30 N34B 1.53(2) . ?
C30 N31B 1.56(2) . ?
C30 H30 1.0000 . ?
N31 O32 1.207(4) . ?
N31 O33 1.221(4) . ?
N34 O35 1.203(4) . ?
N34 O36 1.206(4) . ?
N31B O32B 1.195(17) . ?
N31B O33B 1.201(16) . ?
N34B O35B 1.179(17) . ?
N34B O36B 1.190(17) . ?
O37 N39 1.214(2) . ?
O38 N39 1.205(3) . ?
N39 C40 1.514(3) . ?
C40 C44 1.483(3) . ?
C40 N41 1.501(3) . ?
C40 H40 1.0000 . ?
N41 O43 1.203(3) . ?
N41 O42 1.217(3) . ?
C44 N45 1.325(2) . ?
C44 N48 1.353(2) . ?
N45 N46 1.349(2) . ?
N46 C47 1.334(2) . ?
N46 H46 0.8800 . ?
C47 N48 1.333(2) . ?
C47 C49 1.455(3) . ?
C49 N50 1.304(2) . ?
C49 C53 1.435(3) . ?
N50 O51 1.380(2) . ?
O51 N52 1.361(2) . ?
N52 C53 1.308(3) . ?
C53 N54 1.405(2) . ?
N54 N55 1.257(2) . ?
N55 C56 1.422(2) . ?
C56 N57 1.307(2) . ?
C56 C60 1.428(3) . ?
N57 O58 1.369(2) . ?
O58 N59 1.385(2) . ?
N59 C60 1.310(2) . ?
C60 C61 1.450(3) . ?
C61 N65 1.327(2) . ?
C61 N62 1.338(2) . ?
N62 N63 1.345(2) . ?
N62 H62 0.8800 . ?
N63 C64 1.322(2) . ?
C64 N65 1.354(2) . ?
C64 C66 1.494(3) . ?
C66 N67 1.508(3) . ?
C66 N70 1.515(3) . ?
C66 H66 1.0000 . ?
N67 O69 1.205(3) . ?
N67 O68 1.222(3) . ?
N70 O71 1.201(3) . ?
N70 O72 1.218(2) . ?
O73 N75 1.200(3) . ?
O74 N75 1.208(3) . ?
N75 C76 1.509(3) . ?
C76 C80 1.486(3) . ?
C76 N77 1.504(3) . ?
C76 H76 1.0000 . ?
N77 O79 1.204(3) . ?
N77 O78 1.220(3) . ?
C80 N81 1.323(2) . ?
C80 N84 1.356(3) . ?
N81 N82 1.344(2) . ?
N82 C83 1.338(2) . ?
N82 H82 0.8800 . ?
C83 N84 1.328(2) . ?
C83 C85 1.453(3) . ?
C85 N86 1.310(2) . ?
C85 C89 1.419(3) . ?
N86 O87 1.385(2) . ?
O87 N88 1.370(2) . ?
N88 C89 1.310(3) . ?
C89 N90 1.421(2) . ?
N90 N91 1.254(2) . ?
N91 C92 1.410(2) . ?
C92 N93 1.311(2) . ?
C92 C96 1.433(3) . ?
N93 O94 1.360(2) . ?
O94 N95 1.375(2) . ?
N95 C96 1.309(2) . ?
C96 C97 1.459(3) . ?
C97 N101 1.329(2) . ?
C97 N98 1.334(2) . ?
N98 N99 1.349(2) . ?
N98 H98 0.8800 . ?
N99 C100 1.323(2) . ?
C100 N101 1.352(2) . ?
C100 C102 1.488(3) . ?
C102 N103 1.513(3) . ?
C102 N106 1.516(3) . ?
C102 H102 1.0000 . ?
N103 O104 1.211(3) . ?
N103 O105 1.218(3) . ?
N106 O108 1.202(3) . ?
N106 O107 1.221(2) . ?
O109 N111 1.218(2) . ?
O110 N111 1.217(2) . ?
N111 C112 1.507(3) . ?
C112 C116 1.483(3) . ?
C112 N113 1.520(3) . ?
C112 H112 1.0000 . ?
N113 O114 1.208(3) . ?
N113 O115 1.210(2) . ?
C116 N117 1.322(2) . ?
C116 N120 1.363(2) . ?
N117 N118 1.353(2) . ?
N118 C119 1.338(2) . ?
N118 H118 0.8800 . ?
C119 N120 1.333(2) . ?
C119 C121 1.457(3) . ?
C121 N122 1.304(2) . ?
C121 C125 1.424(3) . ?
N122 O123 1.380(2) . ?
O123 N124 1.363(2) . ?
N124 C125 1.306(3) . ?
C125 N126 1.421(2) . ?
N126 N127 1.260(2) . ?
N127 C128 1.407(2) . ?
C128 N129 1.310(2) . ?
C128 C132 1.432(3) . ?
N129 O130 1.360(2) . ?
O130 N131 1.378(2) . ?
N131 C132 1.302(2) . ?
C132 C133 1.456(3) . ?
C133 N134 1.335(2) . ?
C133 N137 1.337(2) . ?
N134 N135 1.343(2) . ?
N134 H134 0.8800 . ?
N135 C136 1.321(2) . ?
C136 N137 1.350(2) . ?
C136 C138 1.488(3) . ?
C138 N139 1.513(3) . ?
C138 N142 1.518(3) . ?
C138 H138 1.0000 . ?
N139 O141 1.206(2) . ?
N139 O140 1.213(2) . ?
N142 O143 1.209(2) . ?
N142 O144 1.208(2) . ?
C145 C146 1.451(4) . ?
C145 H14A 0.9800 . ?
C145 H14B 0.9800 . ?
C145 H14C 0.9800 . ?
C146 N147 1.144(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 125.9(2) . . ?
O1 N3 C4 117.6(2) . . ?
O2 N3 C4 115.9(2) . . ?
C8 C4 N5 114.58(17) . . ?
C8 C4 N3 112.07(17) . . ?
N5 C4 N3 105.31(18) . . ?
C8 C4 H4 108.2 . . ?
N5 C4 H4 108.2 . . ?
N3 C4 H4 108.2 . . ?
O6 N5 O7 121.6(3) . . ?
O7 N5 O6B 125.3(4) . . ?
O6 N5 C4 121.2(2) . . ?
O7 N5 C4 116.4(2) . . ?
O6B N5 C4 101.8(5) . . ?
N9 C8 N12 115.45(18) . . ?
N9 C8 C4 124.30(18) . . ?
N12 C8 C4 120.18(17) . . ?
C8 N9 N10 101.93(15) . . ?
C11 N10 N9 110.45(16) . . ?
C11 N10 H10 124.8 . . ?
N9 N10 H10 124.8 . . ?
N10 C11 N12 110.01(17) . . ?
N10 C11 C13 127.76(18) . . ?
N12 C11 C13 122.20(17) . . ?
C11 N12 C8 102.15(15) . . ?
N14 C13 C17 107.97(17) . . ?
N14 C13 C11 117.02(18) . . ?
C17 C13 C11 134.91(17) . . ?
C13 N14 O15 106.00(16) . . ?
N16 O15 N14 111.57(14) . . ?
C17 N16 O15 105.54(17) . . ?
N16 C17 N18 115.24(18) . . ?
N16 C17 C13 108.91(17) . . ?
N18 C17 C13 135.84(18) . . ?
N19 N18 C17 112.87(16) . . ?
N18 N19 C20 111.60(16) . . ?
N21 C20 N19 123.69(17) . . ?
N21 C20 C24 109.56(17) . . ?
N19 C20 C24 126.74(17) . . ?
C20 N21 O22 104.70(16) . . ?
N21 O22 N23 111.91(15) . . ?
C24 N23 O22 105.34(16) . . ?
N23 C24 C20 108.47(17) . . ?
N23 C24 C25 121.49(18) . . ?
C20 C24 C25 130.03(17) . . ?
N29 C25 N26 110.34(17) . . ?
N29 C25 C24 125.09(17) . . ?
N26 C25 C24 124.57(17) . . ?
C25 N26 N27 110.10(15) . . ?
C25 N26 H26 124.9 . . ?
N27 N26 H26 124.9 . . ?
C28 N27 N26 102.29(15) . . ?
N27 C28 N29 115.24(17) . . ?
N27 C28 C30 122.48(18) . . ?
N29 C28 C30 122.28(17) . . ?
C25 N29 C28 102.03(16) . . ?
C28 C30 N31 110.70(18) . . ?
C28 C30 N34 111.9(2) . . ?
N31 C30 N34 107.8(2) . . ?
C28 C30 N34B 109.7(8) . . ?
C28 C30 N31B 112.2(7) . . ?
N34B C30 N31B 102.0(11) . . ?
C28 C30 H30 108.8 . . ?
N31 C30 H30 108.8 . . ?
N34 C30 H30 108.8 . . ?
O32 N31 O33 126.0(3) . . ?
O32 N31 C30 118.7(3) . . ?
O33 N31 C30 115.2(3) . . ?
O35 N34 O36 125.8(3) . . ?
O35 N34 C30 118.2(3) . . ?
O36 N34 C30 115.8(3) . . ?
O32B N31B O33B 124(2) . . ?
O32B N31B C30 121.2(18) . . ?
O33B N31B C30 115.0(15) . . ?
O35B N34B O36B 129(3) . . ?
O35B N34B C30 110.7(19) . . ?
O36B N34B C30 120(2) . . ?
O38 N39 O37 126.6(2) . . ?
O38 N39 C40 115.58(19) . . ?
O37 N39 C40 117.78(19) . . ?
C44 C40 N41 113.26(17) . . ?
C44 C40 N39 112.82(17) . . ?
N41 C40 N39 106.75(17) . . ?
C44 C40 H40 107.9 . . ?
N41 C40 H40 107.9 . . ?
N39 C40 H40 107.9 . . ?
O43 N41 O42 126.8(3) . . ?
O43 N41 C40 117.9(2) . . ?
O42 N41 C40 115.3(2) . . ?
N45 C44 N48 115.41(17) . . ?
N45 C44 C40 123.79(17) . . ?
N48 C44 C40 120.80(17) . . ?
C44 N45 N46 102.17(15) . . ?
C47 N46 N45 110.02(15) . . ?
C47 N46 H46 125.0 . . ?
N45 N46 H46 125.0 . . ?
N48 C47 N46 110.55(16) . . ?
N48 C47 C49 121.57(16) . . ?
N46 C47 C49 127.85(17) . . ?
C47 N48 C44 101.85(15) . . ?
N50 C49 C53 107.89(17) . . ?
N50 C49 C47 116.49(17) . . ?
C53 C49 C47 135.62(17) . . ?
C49 N50 O51 106.20(16) . . ?
N52 O51 N50 111.07(14) . . ?
C53 N52 O51 105.89(16) . . ?
N52 C53 N54 114.86(17) . . ?
N52 C53 C49 108.93(17) . . ?
N54 C53 C49 136.20(18) . . ?
N55 N54 C53 113.25(16) . . ?
N54 N55 C56 111.75(16) . . ?
N57 C56 N55 125.13(18) . . ?
N57 C56 C60 109.55(17) . . ?
N55 C56 C60 125.31(17) . . ?
C56 N57 O58 105.17(16) . . ?
N57 O58 N59 111.59(14) . . ?
C60 N59 O58 105.29(16) . . ?
N59 C60 C56 108.39(17) . . ?
N59 C60 C61 121.65(17) . . ?
C56 C60 C61 129.92(17) . . ?
N65 C61 N62 110.67(17) . . ?
N65 C61 C60 125.01(17) . . ?
N62 C61 C60 124.19(16) . . ?
C61 N62 N63 109.93(15) . . ?
C61 N62 H62 125.0 . . ?
N63 N62 H62 125.0 . . ?
C64 N63 N62 102.13(16) . . ?
N63 C64 N65 115.62(17) . . ?
N63 C64 C66 121.99(17) . . ?
N65 C64 C66 122.36(16) . . ?
C61 N65 C64 101.65(15) . . ?
C64 C66 N67 109.40(16) . . ?
C64 C66 N70 113.45(17) . . ?
N67 C66 N70 105.97(16) . . ?
C64 C66 H66 109.3 . . ?
N67 C66 H66 109.3 . . ?
N70 C66 H66 109.3 . . ?
O69 N67 O68 126.0(2) . . ?
O69 N67 C66 115.8(2) . . ?
O68 N67 C66 118.1(2) . . ?
O71 N70 O72 126.2(2) . . ?
O71 N70 C66 118.51(18) . . ?
O72 N70 C66 115.3(2) . . ?
O73 N75 O74 125.0(2) . . ?
O73 N75 C76 119.6(2) . . ?
O74 N75 C76 115.4(2) . . ?
C80 C76 N77 112.05(17) . . ?
C80 C76 N75 112.25(18) . . ?
N77 C76 N75 106.75(17) . . ?
C80 C76 H76 108.6 . . ?
N77 C76 H76 108.6 . . ?
N75 C76 H76 108.6 . . ?
O79 N77 O78 127.7(2) . . ?
O79 N77 C76 114.3(2) . . ?
O78 N77 C76 118.0(2) . . ?
N81 C80 N84 115.60(17) . . ?
N81 C80 C76 122.99(18) . . ?
N84 C80 C76 121.36(17) . . ?
C80 N81 N82 102.05(16) . . ?
C83 N82 N81 110.11(15) . . ?
C83 N82 H82 124.9 . . ?
N81 N82 H82 124.9 . . ?
N84 C83 N82 110.59(17) . . ?
N84 C83 C85 125.33(17) . . ?
N82 C83 C85 124.03(17) . . ?
C83 N84 C80 101.63(16) . . ?
N86 C85 C89 108.76(18) . . ?
N86 C85 C83 121.71(18) . . ?
C89 C85 C83 129.52(17) . . ?
C85 N86 O87 105.10(16) . . ?
N88 O87 N86 111.59(15) . . ?
C89 N88 O87 105.02(16) . . ?
N88 C89 C85 109.53(17) . . ?
N88 C89 N90 125.07(18) . . ?
C85 C89 N90 125.39(17) . . ?
N91 N90 C89 112.14(16) . . ?
N90 N91 C92 113.22(16) . . ?
N93 C92 N91 114.66(17) . . ?
N93 C92 C96 109.04(17) . . ?
N91 C92 C96 136.22(18) . . ?
C92 N93 O94 105.61(16) . . ?
N93 O94 N95 111.51(14) . . ?
C96 N95 O94 106.02(15) . . ?
N95 C96 C92 107.80(17) . . ?
N95 C96 C97 116.24(17) . . ?
C92 C96 C97 135.91(17) . . ?
N101 C97 N98 110.61(16) . . ?
N101 C97 C96 121.27(16) . . ?
N98 C97 C96 128.11(17) . . ?
C97 N98 N99 109.78(15) . . ?
C97 N98 H98 125.1 . . ?
N99 N98 H98 125.1 . . ?
C100 N99 N98 102.34(15) . . ?
N99 C100 N101 115.24(17) . . ?
N99 C100 C102 122.48(17) . . ?
N101 C100 C102 122.28(16) . . ?
C97 N101 C100 102.01(15) . . ?
C100 C102 N103 108.88(16) . . ?
C100 C102 N106 112.76(17) . . ?
N103 C102 N106 106.82(16) . . ?
C100 C102 H102 109.4 . . ?
N103 C102 H102 109.4 . . ?
N106 C102 H102 109.4 . . ?
O104 N103 O105 126.7(2) . . ?
O104 N103 C102 115.64(19) . . ?
O105 N103 C102 117.6(2) . . ?
O108 N106 O107 126.5(2) . . ?
O108 N106 C102 118.52(18) . . ?
O107 N106 C102 114.9(2) . . ?
O110 N111 O109 126.34(19) . . ?
O110 N111 C112 115.55(18) . . ?
O109 N111 C112 118.11(18) . . ?
C116 C112 N111 114.40(16) . . ?
C116 C112 N113 113.19(16) . . ?
N111 C112 N113 106.59(16) . . ?
C116 C112 H112 107.4 . . ?
N111 C112 H112 107.4 . . ?
N113 C112 H112 107.4 . . ?
O114 N113 O115 127.0(2) . . ?
O114 N113 C112 114.59(19) . . ?
O115 N113 C112 118.24(18) . . ?
N117 C116 N120 115.31(17) . . ?
N117 C116 C112 123.89(17) . . ?
N120 C116 C112 120.80(16) . . ?
C116 N117 N118 102.11(15) . . ?
C119 N118 N117 110.36(15) . . ?
C119 N118 H118 124.8 . . ?
N117 N118 H118 124.8 . . ?
N120 C119 N118 110.18(16) . . ?
N120 C119 C121 125.12(16) . . ?
N118 C119 C121 124.70(17) . . ?
C119 N120 C116 102.05(15) . . ?
N122 C121 C125 108.59(17) . . ?
N122 C121 C119 121.51(17) . . ?
C125 C121 C119 129.90(17) . . ?
C121 N122 O123 105.13(16) . . ?
N124 O123 N122 111.89(14) . . ?
C125 N124 O123 105.01(16) . . ?
N124 C125 N126 123.65(17) . . ?
N124 C125 C121 109.37(17) . . ?
N126 C125 C121 126.94(17) . . ?
N127 N126 C125 111.41(15) . . ?
N126 N127 C128 112.86(16) . . ?
N129 C128 N127 115.54(17) . . ?
N129 C128 C132 108.72(17) . . ?
N127 C128 C132 135.58(17) . . ?
C128 N129 O130 105.67(16) . . ?
N129 O130 N131 111.47(14) . . ?
C132 N131 O130 105.79(16) . . ?
N131 C132 C128 108.32(17) . . ?
N131 C132 C133 116.87(17) . . ?
C128 C132 C133 134.47(17) . . ?
N134 C133 N137 110.35(16) . . ?
N134 C133 C132 127.43(17) . . ?
N137 C133 C132 122.13(16) . . ?
C133 N134 N135 110.05(15) . . ?
C133 N134 H134 125.0 . . ?
N135 N134 H134 125.0 . . ?
C136 N135 N134 102.31(15) . . ?
N135 C136 N137 115.64(17) . . ?
N135 C136 C138 120.62(17) . . ?
N137 C136 C138 123.56(17) . . ?
C133 N137 C136 101.64(15) . . ?
C136 C138 N139 108.82(16) . . ?
C136 C138 N142 111.29(16) . . ?
N139 C138 N142 106.85(16) . . ?
C136 C138 H138 109.9 . . ?
N139 C138 H138 109.9 . . ?
N142 C138 H138 109.9 . . ?
O141 N139 O140 126.1(2) . . ?
O141 N139 C138 118.51(19) . . ?
O140 N139 C138 115.26(18) . . ?
O143 N142 O144 125.9(2) . . ?
O143 N142 C138 117.51(18) . . ?
O144 N142 C138 116.56(18) . . ?
C146 C145 H14A 109.5 . . ?
C146 C145 H14B 109.5 . . ?
H14A C145 H14B 109.5 . . ?
C146 C145 H14C 109.5 . . ?
H14A C145 H14C 109.5 . . ?
H14B C145 H14C 109.5 . . ?
N147 C146 C145 178.7(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
O1 N3 C4 C8 0.6(4) . . . . ?
O2 N3 C4 C8 -170.8(2) . . . . ?
O1 N3 C4 N5 -124.6(3) . . . . ?
O2 N3 C4 N5 64.0(3) . . . . ?
C8 C4 N5 O6 -25.9(5) . . . . ?
N3 C4 N5 O6 97.7(5) . . . . ?
C8 C4 N5 O7 144.6(2) . . . . ?
N3 C4 N5 O7 -91.8(3) . . . . ?
C8 C4 N5 O6B -75.7(6) . . . . ?
N3 C4 N5 O6B 47.9(6) . . . . ?
N5 C4 C8 N9 44.9(3) . . . . ?
N3 C4 C8 N9 -75.0(3) . . . . ?
N5 C4 C8 N12 -138.1(2) . . . . ?
N3 C4 C8 N12 101.9(2) . . . . ?
N12 C8 N9 N10 0.8(2) . . . . ?
C4 C8 N9 N10 177.86(18) . . . . ?
C8 N9 N10 C11 -1.0(2) . . . . ?
N9 N10 C11 N12 0.9(2) . . . . ?
N9 N10 C11 C13 -176.98(18) . . . . ?
N10 C11 N12 C8 -0.4(2) . . . . ?
C13 C11 N12 C8 177.64(18) . . . . ?
N9 C8 N12 C11 -0.3(2) . . . . ?
C4 C8 N12 C11 -177.49(18) . . . . ?
N10 C11 C13 N14 -175.21(19) . . . . ?
N12 C11 C13 N14 7.2(3) . . . . ?
N10 C11 C13 C17 9.0(4) . . . . ?
N12 C11 C13 C17 -168.6(2) . . . . ?
C17 C13 N14 O15 0.9(2) . . . . ?
C11 C13 N14 O15 -175.98(16) . . . . ?
C13 N14 O15 N16 -0.1(2) . . . . ?
N14 O15 N16 C17 -0.8(2) . . . . ?
O15 N16 C17 N18 -177.99(17) . . . . ?
O15 N16 C17 C13 1.3(2) . . . . ?
N14 C13 C17 N16 -1.4(2) . . . . ?
C11 C13 C17 N16 174.6(2) . . . . ?
N14 C13 C17 N18 177.7(2) . . . . ?
C11 C13 C17 N18 -6.3(4) . . . . ?
N16 C17 N18 N19 170.93(19) . . . . ?
C13 C17 N18 N19 -8.1(3) . . . . ?
C17 N18 N19 C20 -177.63(17) . . . . ?
N18 N19 C20 N21 7.7(3) . . . . ?
N18 N19 C20 C24 -173.52(19) . . . . ?
N19 C20 N21 O22 179.41(18) . . . . ?
C24 C20 N21 O22 0.5(2) . . . . ?
C20 N21 O22 N23 -0.1(2) . . . . ?
N21 O22 N23 C24 -0.3(2) . . . . ?
O22 N23 C24 C20 0.6(2) . . . . ?
O22 N23 C24 C25 179.86(18) . . . . ?
N21 C20 C24 N23 -0.7(2) . . . . ?
N19 C20 C24 N23 -179.59(19) . . . . ?
N21 C20 C24 C25 -179.9(2) . . . . ?
N19 C20 C24 C25 1.2(3) . . . . ?
N23 C24 C25 N29 -179.5(2) . . . . ?
C20 C24 C25 N29 -0.4(3) . . . . ?
N23 C24 C25 N26 0.1(3) . . . . ?
C20 C24 C25 N26 179.2(2) . . . . ?
N29 C25 N26 N27 0.6(2) . . . . ?
C24 C25 N26 N27 -179.01(18) . . . . ?
C25 N26 N27 C28 -0.4(2) . . . . ?
N26 N27 C28 N29 0.0(2) . . . . ?
N26 N27 C28 C30 179.03(18) . . . . ?
N26 C25 N29 C28 -0.6(2) . . . . ?
C24 C25 N29 C28 179.04(19) . . . . ?
N27 C28 N29 C25 0.4(2) . . . . ?
C30 C28 N29 C25 -178.66(19) . . . . ?
N27 C28 C30 N31 29.2(3) . . . . ?
N29 C28 C30 N31 -151.8(2) . . . . ?
N27 C28 C30 N34 -91.1(3) . . . . ?
N29 C28 C30 N34 87.9(3) . . . . ?
N27 C28 C30 N34B -49.6(9) . . . . ?
N29 C28 C30 N34B 129.4(9) . . . . ?
N27 C28 C30 N31B 62.9(10) . . . . ?
N29 C28 C30 N31B -118.1(9) . . . . ?
C28 C30 N31 O32 -84.2(3) . . . . ?
N34 C30 N31 O32 38.5(3) . . . . ?
C28 C30 N31 O33 92.2(3) . . . . ?
N34 C30 N31 O33 -145.1(3) . . . . ?
C28 C30 N34 O35 -8.1(4) . . . . ?
N31 C30 N34 O35 -130.1(3) . . . . ?
C28 C30 N34 O36 175.7(3) . . . . ?
N31 C30 N34 O36 53.7(4) . . . . ?
C28 C30 N31B O32B -37(3) . . . . ?
N34B C30 N31B O32B 80(3) . . . . ?
C28 C30 N31B O33B 147.1(17) . . . . ?
N34B C30 N31B O33B -96(2) . . . . ?
C28 C30 N34B O35B -69(2) . . . . ?
N31B C30 N34B O35B 171.9(19) . . . . ?
C28 C30 N34B O36B 105(3) . . . . ?
N31B C30 N34B O36B -14(3) . . . . ?
O38 N39 C40 C44 -38.1(3) . . . . ?
O37 N39 C40 C44 144.82(19) . . . . ?
O38 N39 C40 N41 -163.2(2) . . . . ?
O37 N39 C40 N41 19.8(3) . . . . ?
C44 C40 N41 O43 -52.6(3) . . . . ?
N39 C40 N41 O43 72.1(2) . . . . ?
C44 C40 N41 O42 126.4(2) . . . . ?
N39 C40 N41 O42 -108.8(2) . . . . ?
N41 C40 C44 N45 64.5(3) . . . . ?
N39 C40 C44 N45 -56.9(3) . . . . ?
N41 C40 C44 N48 -115.2(2) . . . . ?
N39 C40 C44 N48 123.4(2) . . . . ?
N48 C44 N45 N46 -0.3(2) . . . . ?
C40 C44 N45 N46 179.96(18) . . . . ?
C44 N45 N46 C47 0.0(2) . . . . ?
N45 N46 C47 N48 0.4(2) . . . . ?
N45 N46 C47 C49 -177.82(18) . . . . ?
N46 C47 N48 C44 -0.5(2) . . . . ?
C49 C47 N48 C44 177.81(17) . . . . ?
N45 C44 N48 C47 0.5(2) . . . . ?
C40 C44 N48 C47 -179.74(18) . . . . ?
N48 C47 C49 N50 -4.1(3) . . . . ?
N46 C47 C49 N50 173.97(19) . . . . ?
N48 C47 C49 C53 175.8(2) . . . . ?
N46 C47 C49 C53 -6.2(4) . . . . ?
C53 C49 N50 O51 -0.4(2) . . . . ?
C47 C49 N50 O51 179.52(16) . . . . ?
C49 N50 O51 N52 -0.2(2) . . . . ?
N50 O51 N52 C53 0.8(2) . . . . ?
O51 N52 C53 N54 179.57(16) . . . . ?
O51 N52 C53 C49 -1.0(2) . . . . ?
N50 C49 C53 N52 0.9(2) . . . . ?
C47 C49 C53 N52 -179.0(2) . . . . ?
N50 C49 C53 N54 -179.9(2) . . . . ?
C47 C49 C53 N54 0.3(4) . . . . ?
N52 C53 N54 N55 -175.79(18) . . . . ?
C49 C53 N54 N55 5.0(3) . . . . ?
C53 N54 N55 C56 -177.27(16) . . . . ?
N54 N55 C56 N57 0.5(3) . . . . ?
N54 N55 C56 C60 178.96(18) . . . . ?
N55 C56 N57 O58 179.01(18) . . . . ?
C60 C56 N57 O58 0.3(2) . . . . ?
C56 N57 O58 N59 -0.7(2) . . . . ?
N57 O58 N59 C60 0.8(2) . . . . ?
O58 N59 C60 C56 -0.5(2) . . . . ?
O58 N59 C60 C61 -178.59(17) . . . . ?
N57 C56 C60 N59 0.1(2) . . . . ?
N55 C56 C60 N59 -178.55(18) . . . . ?
N57 C56 C60 C61 177.98(19) . . . . ?
N55 C56 C60 C61 -0.7(3) . . . . ?
N59 C60 C61 N65 162.40(19) . . . . ?
C56 C60 C61 N65 -15.2(3) . . . . ?
N59 C60 C61 N62 -13.1(3) . . . . ?
C56 C60 C61 N62 169.23(19) . . . . ?
N65 C61 N62 N63 -0.4(2) . . . . ?
C60 C61 N62 N63 175.66(17) . . . . ?
C61 N62 N63 C64 0.1(2) . . . . ?
N62 N63 C64 N65 0.3(2) . . . . ?
N62 N63 C64 C66 -177.41(17) . . . . ?
N62 C61 N65 C64 0.6(2) . . . . ?
C60 C61 N65 C64 -175.48(18) . . . . ?
N63 C64 N65 C61 -0.6(2) . . . . ?
C66 C64 N65 C61 177.15(18) . . . . ?
N63 C64 C66 N67 26.5(3) . . . . ?
N65 C64 C66 N67 -151.10(19) . . . . ?
N63 C64 C66 N70 -91.6(2) . . . . ?
N65 C64 C66 N70 90.8(2) . . . . ?
C64 C66 N67 O69 82.3(2) . . . . ?
N70 C66 N67 O69 -155.00(19) . . . . ?
C64 C66 N67 O68 -95.0(2) . . . . ?
N70 C66 N67 O68 27.6(3) . . . . ?
C64 C66 N70 O71 5.5(3) . . . . ?
N67 C66 N70 O71 -114.6(2) . . . . ?
C64 C66 N70 O72 -173.53(18) . . . . ?
N67 C66 N70 O72 66.4(2) . . . . ?
O73 N75 C76 C80 -33.1(3) . . . . ?
O74 N75 C76 C80 146.7(2) . . . . ?
O73 N75 C76 N77 90.0(3) . . . . ?
O74 N75 C76 N77 -90.1(2) . . . . ?
C80 C76 N77 O79 -64.7(3) . . . . ?
N75 C76 N77 O79 172.0(2) . . . . ?
C80 C76 N77 O78 116.1(2) . . . . ?
N75 C76 N77 O78 -7.1(3) . . . . ?
N77 C76 C80 N81 -40.0(3) . . . . ?
N75 C76 C80 N81 80.1(2) . . . . ?
N77 C76 C80 N84 142.87(19) . . . . ?
N75 C76 C80 N84 -97.0(2) . . . . ?
N84 C80 N81 N82 0.5(2) . . . . ?
C76 C80 N81 N82 -176.80(18) . . . . ?
C80 N81 N82 C83 0.6(2) . . . . ?
N81 N82 C83 N84 -1.4(2) . . . . ?
N81 N82 C83 C85 176.29(17) . . . . ?
N82 C83 N84 C80 1.6(2) . . . . ?
C85 C83 N84 C80 -176.11(18) . . . . ?
N81 C80 N84 C83 -1.3(2) . . . . ?
C76 C80 N84 C83 176.04(18) . . . . ?
N84 C83 C85 N86 158.2(2) . . . . ?
N82 C83 C85 N86 -19.2(3) . . . . ?
N84 C83 C85 C89 -21.0(3) . . . . ?
N82 C83 C85 C89 161.6(2) . . . . ?
C89 C85 N86 O87 -0.4(2) . . . . ?
C83 C85 N86 O87 -179.71(17) . . . . ?
C85 N86 O87 N88 0.7(2) . . . . ?
N86 O87 N88 C89 -0.7(2) . . . . ?
O87 N88 C89 C85 0.4(2) . . . . ?
O87 N88 C89 N90 -178.41(18) . . . . ?
N86 C85 C89 N88 0.0(2) . . . . ?
C83 C85 C89 N88 179.22(19) . . . . ?
N86 C85 C89 N90 178.81(18) . . . . ?
C83 C85 C89 N90 -1.9(3) . . . . ?
N88 C89 N90 N91 6.2(3) . . . . ?
C85 C89 N90 N91 -172.45(18) . . . . ?
C89 N90 N91 C92 177.64(16) . . . . ?
N90 N91 C92 N93 -174.77(17) . . . . ?
N90 N91 C92 C96 1.6(3) . . . . ?
N91 C92 N93 O94 176.86(16) . . . . ?
C96 C92 N93 O94 -0.5(2) . . . . ?
C92 N93 O94 N95 -0.1(2) . . . . ?
N93 O94 N95 C96 0.7(2) . . . . ?
O94 N95 C96 C92 -0.9(2) . . . . ?
O94 N95 C96 C97 177.20(16) . . . . ?
N93 C92 C96 N95 0.9(2) . . . . ?
N91 C92 C96 N95 -175.6(2) . . . . ?
N93 C92 C96 C97 -176.7(2) . . . . ?
N91 C92 C96 C97 6.9(4) . . . . ?
N95 C96 C97 N101 -7.5(3) . . . . ?
C92 C96 C97 N101 169.9(2) . . . . ?
N95 C96 C97 N98 171.77(19) . . . . ?
C92 C96 C97 N98 -10.8(4) . . . . ?
N101 C97 N98 N99 0.9(2) . . . . ?
C96 C97 N98 N99 -178.42(18) . . . . ?
C97 N98 N99 C100 -0.6(2) . . . . ?
N98 N99 C100 N101 0.2(2) . . . . ?
N98 N99 C100 C102 -179.59(17) . . . . ?
N98 C97 N101 C100 -0.7(2) . . . . ?
C96 C97 N101 C100 178.67(17) . . . . ?
N99 C100 N101 C97 0.3(2) . . . . ?
C102 C100 N101 C97 -179.90(18) . . . . ?
N99 C100 C102 N103 20.6(3) . . . . ?
N101 C100 C102 N103 -159.14(18) . . . . ?
N99 C100 C102 N106 -97.7(2) . . . . ?
N101 C100 C102 N106 82.5(2) . . . . ?
C100 C102 N103 O104 87.0(2) . . . . ?
N106 C102 N103 O104 -150.96(19) . . . . ?
C100 C102 N103 O105 -90.4(2) . . . . ?
N106 C102 N103 O105 31.7(2) . . . . ?
C100 C102 N106 O108 8.7(3) . . . . ?
N103 C102 N106 O108 -110.8(2) . . . . ?
C100 C102 N106 O107 -170.01(18) . . . . ?
N103 C102 N106 O107 70.4(2) . . . . ?
O110 N111 C112 C116 131.4(2) . . . . ?
O109 N111 C112 C116 -48.9(3) . . . . ?
O110 N111 C112 N113 -102.7(2) . . . . ?
O109 N111 C112 N113 77.0(2) . . . . ?
C116 C112 N113 O114 -41.9(3) . . . . ?
N111 C112 N113 O114 -168.5(2) . . . . ?
C116 C112 N113 O115 143.07(19) . . . . ?
N111 C112 N113 O115 16.4(2) . . . . ?
N111 C112 C116 N117 61.7(3) . . . . ?
N113 C112 C116 N117 -60.7(2) . . . . ?
N111 C112 C116 N120 -118.5(2) . . . . ?
N113 C112 C116 N120 119.1(2) . . . . ?
N120 C116 N117 N118 -0.2(2) . . . . ?
C112 C116 N117 N118 179.59(17) . . . . ?
C116 N117 N118 C119 0.3(2) . . . . ?
N117 N118 C119 N120 -0.2(2) . . . . ?
N117 N118 C119 C121 -179.87(18) . . . . ?
N118 C119 N120 C116 0.1(2) . . . . ?
C121 C119 N120 C116 179.73(18) . . . . ?
N117 C116 N120 C119 0.1(2) . . . . ?
C112 C116 N120 C119 -179.72(17) . . . . ?
N120 C119 C121 N122 169.80(19) . . . . ?
N118 C119 C121 N122 -10.6(3) . . . . ?
N120 C119 C121 C125 -11.1(3) . . . . ?
N118 C119 C121 C125 168.5(2) . . . . ?
C125 C121 N122 O123 1.0(2) . . . . ?
C119 C121 N122 O123 -179.71(17) . . . . ?
C121 N122 O123 N124 -0.2(2) . . . . ?
N122 O123 N124 C125 -0.7(2) . . . . ?
O123 N124 C125 N126 179.10(17) . . . . ?
O123 N124 C125 C121 1.3(2) . . . . ?
N122 C121 C125 N124 -1.5(2) . . . . ?
C119 C121 C125 N124 179.3(2) . . . . ?
N122 C121 C125 N126 -179.24(19) . . . . ?
C119 C121 C125 N126 1.6(3) . . . . ?
N124 C125 N126 N127 16.7(3) . . . . ?
C121 C125 N126 N127 -165.82(19) . . . . ?
C125 N126 N127 C128 -174.89(16) . . . . ?
N126 N127 C128 N129 165.68(18) . . . . ?
N126 N127 C128 C132 -9.3(3) . . . . ?
N127 C128 N129 O130 -174.82(17) . . . . ?
C132 C128 N129 O130 1.5(2) . . . . ?
C128 N129 O130 N131 -1.3(2) . . . . ?
N129 O130 N131 C132 0.6(2) . . . . ?
O130 N131 C132 C128 0.3(2) . . . . ?
O130 N131 C132 C133 -173.99(16) . . . . ?
N129 C128 C132 N131 -1.1(2) . . . . ?
N127 C128 C132 N131 174.1(2) . . . . ?
N129 C128 C132 C133 171.7(2) . . . . ?
N127 C128 C132 C133 -13.1(4) . . . . ?
N131 C132 C133 N134 -172.44(19) . . . . ?
C128 C132 C133 N134 15.2(3) . . . . ?
N131 C132 C133 N137 11.1(3) . . . . ?
C128 C132 C133 N137 -161.2(2) . . . . ?
N137 C133 N134 N135 0.9(2) . . . . ?
C132 C133 N134 N135 -175.92(18) . . . . ?
C133 N134 N135 C136 -0.6(2) . . . . ?
N134 N135 C136 N137 0.2(2) . . . . ?
N134 N135 C136 C138 175.50(16) . . . . ?
N134 C133 N137 C136 -0.7(2) . . . . ?
C132 C133 N137 C136 176.30(17) . . . . ?
N135 C136 N137 C133 0.3(2) . . . . ?
C138 C136 N137 C133 -174.86(18) . . . . ?
N135 C136 C138 N139 35.5(2) . . . . ?
N137 C136 C138 N139 -149.55(18) . . . . ?
N135 C136 C138 N142 -82.0(2) . . . . ?
N137 C136 C138 N142 93.0(2) . . . . ?
C136 C138 N139 O141 -91.5(2) . . . . ?
N142 C138 N139 O141 28.8(2) . . . . ?
C136 C138 N139 O140 84.6(2) . . . . ?
N142 C138 N139 O140 -155.17(18) . . . . ?
C136 C138 N142 O143 -5.1(3) . . . . ?
N139 C138 N142 O143 -123.8(2) . . . . ?
C136 C138 N142 O144 177.9(2) . . . . ?
N139 C138 N142 O144 59.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 N19 0.88 2.18 2.878(2) 135.5 .
N10 H10 N29 0.88 2.19 2.860(2) 132.7 .
N26 H26 N48 0.88 2.36 2.967(2) 126.1 .
N26 H26 N50 0.88 2.58 3.426(2) 162.6 .
N46 H46 N55 0.88 2.22 2.910(2) 135.2 .
N46 H46 N65 0.88 2.17 2.839(2) 132.9 .
N62 H62 N12 0.88 2.06 2.918(2) 163.9 4_565
N82 H82 N131 0.88 2.62 3.178(2) 121.9 4_676
N82 H82 N137 0.88 2.14 2.954(2) 153.3 4_676
N98 H98 N84 0.88 2.20 2.891(2) 135.6 .
N98 H98 N90 0.88 2.26 2.941(2) 134.2 .
N118 H118 N95 0.88 2.57 3.420(2) 163.5 .
N118 H118 N101 0.88 2.29 2.895(2) 126.3 .
N134 H134 N120 0.88 2.23 2.908(2) 133.8 .
N134 H134 N126 0.88 2.19 2.885(2) 135.0 .

_refine_diff_density_max         0.720
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.067

