# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_shrv741
_database_code_depnum_ccdc_archive 'CCDC 1884779'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_shrv741             
;
PROBLEM: Short Inter D...A Contact  O2       ..N3       .       2.87 Ang.
RESPONSE: High-density energetic materials often display close contacts.
;
# Added during the CSD deposition process: Wednesday 12 December 2018 05:14 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         'C3 H2 N8 O2'
_chemical_formula_sum            'C3 H2 N8 O2'
_chemical_formula_weight         182.13

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   6.9340(2)
_cell_length_b                   12.4025(4)
_cell_length_c                   15.5088(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1333.74(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4975
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.12

_exptl_crystal_description       chunk
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.316
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            14964
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         30.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3793
_reflns_number_gt                3244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.999

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.0537P] 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_abs_structure_details 
;
 Flack x determined using 1375 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_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
O1 O 0.8671(2) 0.39682(12) 0.51640(9) 0.0376(3) Uani 1 1 d . . . . .
O2 O 0.6759(2) 0.25936(13) 0.52282(11) 0.0398(4) Uani 1 1 d . . . . .
N3 N 0.7951(2) 0.32049(13) 0.55665(10) 0.0288(3) Uani 1 1 d . . . . .
N4 N 0.8401(2) 0.29795(15) 0.63924(10) 0.0301(4) Uani 1 1 d . . . . .
C5 C 0.9758(3) 0.36213(15) 0.67233(12) 0.0261(4) Uani 1 1 d . . . . .
N6 N 1.0869(2) 0.44392(15) 0.64457(11) 0.0323(4) Uani 1 1 d . . . . .
H6 H 1.0825 0.4679 0.5926 0.039 Uiso 1 1 calc R U . . .
N7 N 1.2071(3) 0.48579(15) 0.70561(12) 0.0377(4) Uani 1 1 d . . . . .
C8 C 1.1688(3) 0.42746(17) 0.77347(13) 0.0321(4) Uani 1 1 d . . . . .
N9 N 1.2503(3) 0.43623(17) 0.85354(12) 0.0386(4) Uani 1 1 d . . . . .
N10 N 1.1928(2) 0.36985(16) 0.91089(12) 0.0388(4) Uani 1 1 d . . . . .
C11 C 1.0527(3) 0.29347(19) 0.88910(13) 0.0368(5) Uani 1 1 d . . . . .
H11 H 1.0163 0.2467 0.9331 0.044 Uiso 1 1 calc R U . . .
N12 N 0.9672(3) 0.27925(14) 0.81597(11) 0.0328(4) Uani 1 1 d . . . . .
N13 N 1.0297(2) 0.35152(13) 0.75667(10) 0.0280(3) Uani 1 1 d . . . . .
O14 O 0.4057(2) 0.44493(14) 0.49862(10) 0.0428(4) Uani 1 1 d . . . . .
O15 O 0.1722(2) 0.55936(13) 0.48738(11) 0.0432(4) Uani 1 1 d . . . . .
N16 N 0.2895(2) 0.49551(15) 0.45442(11) 0.0315(4) Uani 1 1 d . . . . .
N17 N 0.2796(2) 0.48573(14) 0.36828(11) 0.0314(4) Uani 1 1 d . . . . .
C18 C 0.3984(3) 0.41116(16) 0.33596(12) 0.0272(4) Uani 1 1 d . . . . .
N19 N 0.5225(2) 0.33716(14) 0.36694(11) 0.0330(4) Uani 1 1 d . . . . .
H19 H 0.5455 0.3294 0.4211 0.040 Uiso 1 1 calc R U . . .
N20 N 0.6085(3) 0.27541(15) 0.30502(13) 0.0390(4) Uani 1 1 d . . . . .
C21 C 0.5343(3) 0.31237(16) 0.23394(14) 0.0323(4) Uani 1 1 d . . . . .
N22 N 0.5742(3) 0.27850(16) 0.15178(12) 0.0404(4) Uani 1 1 d . . . . .
N23 N 0.4852(3) 0.32623(16) 0.09053(13) 0.0403(4) Uani 1 1 d . . . . .
C24 C 0.3565(3) 0.40967(18) 0.11030(13) 0.0353(5) Uani 1 1 d . . . . .
H24 H 0.2953 0.4417 0.0635 0.042 Uiso 1 1 calc R U . . .
N25 N 0.3119(2) 0.44792(14) 0.18528(11) 0.0304(4) Uani 1 1 d . . . . .
N26 N 0.4075(2) 0.39468(13) 0.24883(10) 0.0264(3) 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 1.239(2) . ?
O2 N3 1.238(2) . ?
N3 N4 1.348(2) . ?
N4 C5 1.335(2) . ?
C5 N6 1.344(2) . ?
C5 N13 1.367(2) . ?
N6 N7 1.364(2) . ?
N6 H6 0.8600 . ?
N7 C8 1.304(3) . ?
C8 N9 1.369(3) . ?
C8 N13 1.373(2) . ?
N9 N10 1.276(3) . ?
N10 C11 1.398(3) . ?
C11 N12 1.292(3) . ?
C11 H11 0.9300 . ?
N12 N13 1.355(2) . ?
O14 N16 1.230(2) . ?
O15 N16 1.245(2) . ?
N16 N17 1.343(2) . ?
N17 C18 1.336(3) . ?
C18 N19 1.347(3) . ?
C18 N26 1.368(2) . ?
N19 N20 1.365(3) . ?
N19 H19 0.8600 . ?
N20 C21 1.300(3) . ?
C21 N26 1.367(2) . ?
C21 N22 1.370(3) . ?
N22 N23 1.278(3) . ?
N23 C24 1.400(3) . ?
C24 N25 1.294(3) . ?
C24 H24 0.9300 . ?
N25 N26 1.359(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 121.56(17) . . ?
O2 N3 N4 115.50(17) . . ?
O1 N3 N4 122.94(17) . . ?
C5 N4 N3 113.89(17) . . ?
N4 C5 N6 136.93(19) . . ?
N4 C5 N13 120.21(17) . . ?
N6 C5 N13 102.86(16) . . ?
C5 N6 N7 114.52(17) . . ?
C5 N6 H6 122.7 . . ?
N7 N6 H6 122.7 . . ?
C8 N7 N6 102.96(16) . . ?
N7 C8 N9 127.15(19) . . ?
N7 C8 N13 111.74(17) . . ?
N9 C8 N13 121.11(19) . . ?
N10 N9 C8 116.90(18) . . ?
N9 N10 C11 119.06(17) . . ?
N12 C11 N10 128.6(2) . . ?
N12 C11 H11 115.7 . . ?
N10 C11 H11 115.7 . . ?
C11 N12 N13 111.01(17) . . ?
N12 N13 C5 128.73(16) . . ?
N12 N13 C8 123.34(17) . . ?
C5 N13 C8 107.91(16) . . ?
O14 N16 O15 121.58(18) . . ?
O14 N16 N17 122.78(18) . . ?
O15 N16 N17 115.64(17) . . ?
C18 N17 N16 113.85(17) . . ?
N17 C18 N19 137.03(18) . . ?
N17 C18 N26 120.16(16) . . ?
N19 C18 N26 102.78(16) . . ?
C18 N19 N20 114.23(17) . . ?
C18 N19 H19 122.9 . . ?
N20 N19 H19 122.9 . . ?
C21 N20 N19 103.04(16) . . ?
N20 C21 N26 112.01(18) . . ?
N20 C21 N22 126.90(19) . . ?
N26 C21 N22 121.07(18) . . ?
N23 N22 C21 116.84(18) . . ?
N22 N23 C24 119.16(19) . . ?
N25 C24 N23 128.34(19) . . ?
N25 C24 H24 115.8 . . ?
N23 C24 H24 115.8 . . ?
C24 N25 N26 110.92(17) . . ?
N25 N26 C21 123.65(16) . . ?
N25 N26 C18 128.41(16) . . ?
C21 N26 C18 107.94(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 N4 C5 176.91(17) . . . . ?
O1 N3 N4 C5 -3.0(3) . . . . ?
N3 N4 C5 N6 -2.1(3) . . . . ?
N3 N4 C5 N13 177.13(17) . . . . ?
N4 C5 N6 N7 179.3(2) . . . . ?
N13 C5 N6 N7 -0.1(2) . . . . ?
C5 N6 N7 C8 0.1(2) . . . . ?
N6 N7 C8 N9 -179.9(2) . . . . ?
N6 N7 C8 N13 -0.1(2) . . . . ?
N7 C8 N9 N10 -179.3(2) . . . . ?
N13 C8 N9 N10 0.9(3) . . . . ?
C8 N9 N10 C11 0.0(3) . . . . ?
N9 N10 C11 N12 -0.4(4) . . . . ?
N10 C11 N12 N13 -0.3(3) . . . . ?
C11 N12 N13 C5 179.40(19) . . . . ?
C11 N12 N13 C8 1.3(3) . . . . ?
N4 C5 N13 N12 2.2(3) . . . . ?
N6 C5 N13 N12 -178.34(18) . . . . ?
N4 C5 N13 C8 -179.47(17) . . . . ?
N6 C5 N13 C8 0.0(2) . . . . ?
N7 C8 N13 N12 178.51(18) . . . . ?
N9 C8 N13 N12 -1.7(3) . . . . ?
N7 C8 N13 C5 0.0(2) . . . . ?
N9 C8 N13 C5 179.84(19) . . . . ?
O14 N16 N17 C18 4.2(3) . . . . ?
O15 N16 N17 C18 -175.64(17) . . . . ?
N16 N17 C18 N19 4.1(3) . . . . ?
N16 N17 C18 N26 -178.15(17) . . . . ?
N17 C18 N19 N20 177.9(2) . . . . ?
N26 C18 N19 N20 -0.1(2) . . . . ?
C18 N19 N20 C21 -0.3(2) . . . . ?
N19 N20 C21 N26 0.5(2) . . . . ?
N19 N20 C21 N22 179.2(2) . . . . ?
N20 C21 N22 N23 -179.7(2) . . . . ?
N26 C21 N22 N23 -1.1(3) . . . . ?
C21 N22 N23 C24 0.8(3) . . . . ?
N22 N23 C24 N25 0.1(4) . . . . ?
N23 C24 N25 N26 -0.7(3) . . . . ?
C24 N25 N26 C21 0.4(3) . . . . ?
C24 N25 N26 C18 -179.78(19) . . . . ?
N20 C21 N26 N25 179.30(18) . . . . ?
N22 C21 N26 N25 0.5(3) . . . . ?
N20 C21 N26 C18 -0.6(2) . . . . ?
N22 C21 N26 C18 -179.37(19) . . . . ?
N17 C18 N26 N25 2.1(3) . . . . ?
N19 C18 N26 N25 -179.51(18) . . . . ?
N17 C18 N26 C21 -178.05(17) . . . . ?
N19 C18 N26 C21 0.3(2) . . . . ?

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
N19 H19 O2 0.86 2.02 2.812(2) 153.6 .
N19 H19 O14 0.86 2.11 2.571(2) 113.3 .
N6 H6 O1 0.86 2.10 2.572(2) 114.1 .
N6 H6 O15 0.86 2.08 2.888(2) 155.8 1_655
N6 H6 N16 0.86 2.60 3.328(2) 143.0 1_655
C24 H24 O1 0.93 2.41 3.207(3) 143.6 2_664
C24 H24 N10 0.93 2.63 3.331(3) 133.0 1_454
C11 H11 N10 0.93 2.69 3.232(3) 117.9 3_455
C11 H11 N23 0.93 2.61 3.490(3) 157.4 3_556

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_shrv747
_database_code_depnum_ccdc_archive 'CCDC 1884784'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-08 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         'C3 N11 O2, H4 N O'
_chemical_formula_sum            'C3 H4 N12 O3'
_chemical_formula_weight         256.18

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   7.7496(12)
_cell_length_b                   4.9302(8)
_cell_length_c                   12.611(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.872(5)
_cell_angle_gamma                90
_cell_volume                     476.05(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1461
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      23.01

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_F_000             260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            5552
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.900
_diffrn_reflns_theta_max         29.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2604
_reflns_number_gt                1866
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.925
_reflns_Friedel_fraction_full    1.000

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²] 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_abs_structure_details 
;
 Flack x determined using 663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2604
_refine_ls_number_parameters     167
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
O1 O 0.5462(3) 1.0639(4) 0.44287(16) 0.0415(5) Uani 1 1 d . . . . .
O2 O 0.7918(3) 0.8443(5) 0.48188(16) 0.0476(5) Uani 1 1 d . . . . .
N3 N 0.6468(3) 0.8742(4) 0.42516(16) 0.0309(5) Uani 1 1 d . . . . .
N4 N 0.5880(3) 0.7150(4) 0.34287(17) 0.0289(5) Uani 1 1 d . . . . .
C5 C 0.6986(3) 0.5175(5) 0.3181(2) 0.0275(5) Uani 1 1 d . . . . .
N6 N 0.8662(3) 0.4520(5) 0.35134(19) 0.0387(6) Uani 1 1 d . . . . .
N7 N 0.9094(3) 0.2334(5) 0.2928(2) 0.0430(6) Uani 1 1 d . . . . .
C8 C 0.7675(4) 0.1710(5) 0.2248(2) 0.0344(6) Uani 1 1 d . . . . .
N9 N 0.7461(4) -0.0318(5) 0.1504(2) 0.0444(6) Uani 1 1 d . . . . .
N10 N 0.5912(4) -0.0626(5) 0.09741(19) 0.0455(6) Uani 1 1 d . . . . .
C11 C 0.4587(4) 0.1083(5) 0.1197(2) 0.0358(7) Uani 1 1 d . . . . .
N12 N 0.2995(4) 0.0315(5) 0.0603(2) 0.0471(7) Uani 1 1 d . . . . .
N13 N 0.1792(4) 0.1943(7) 0.0717(2) 0.0494(7) Uani 1 1 d . . . . .
N14 N 0.0621(5) 0.3252(9) 0.0744(3) 0.0709(9) Uani 1 1 d . . . . .
N15 N 0.4689(3) 0.3150(5) 0.18502(16) 0.0316(5) Uani 1 1 d . . . . .
N16 N 0.6347(3) 0.3409(4) 0.23816(15) 0.0271(5) Uani 1 1 d . . . . .
O17 O 0.2202(3) 0.7496(6) 0.28434(18) 0.0629(7) Uani 1 1 d D . . . .
H17 H 0.325(2) 0.706(10) 0.297(4) 0.094 Uiso 1 1 d D U . . .
N18 N 0.1783(3) 0.8356(5) 0.38232(18) 0.0412(6) Uani 1 1 d . . . . .
H18A H 0.2741 0.8964 0.4235 0.062 Uiso 1 1 calc R U . . .
H18B H 0.1343 0.6972 0.4148 0.062 Uiso 1 1 calc R U . . .
H18C H 0.0996 0.9682 0.3713 0.062 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 1.259(3) . ?
O2 N3 1.244(3) . ?
N3 N4 1.325(3) . ?
N4 C5 1.365(3) . ?
C5 N6 1.341(3) . ?
C5 N16 1.366(3) . ?
N6 N7 1.376(4) . ?
N7 C8 1.322(4) . ?
C8 N16 1.357(3) . ?
C8 N9 1.364(4) . ?
N9 N10 1.290(4) . ?
N10 C11 1.390(4) . ?
C11 N15 1.305(3) . ?
C11 N12 1.393(4) . ?
N12 N13 1.255(4) . ?
N13 N14 1.118(5) . ?
N15 N16 1.361(3) . ?
O17 N18 1.391(3) . ?
O17 H17 0.831(14) . ?
N18 H18A 0.8900 . ?
N18 H18B 0.8900 . ?
N18 H18C 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 121.0(2) . . ?
O2 N3 N4 123.4(2) . . ?
O1 N3 N4 115.5(2) . . ?
N3 N4 C5 116.7(2) . . ?
N6 C5 N4 135.4(2) . . ?
N6 C5 N16 107.5(2) . . ?
N4 C5 N16 117.0(2) . . ?
C5 N6 N7 108.9(2) . . ?
C8 N7 N6 106.5(2) . . ?
N7 C8 N16 110.3(2) . . ?
N7 C8 N9 128.1(3) . . ?
N16 C8 N9 121.6(3) . . ?
N10 N9 C8 116.5(3) . . ?
N9 N10 C11 118.8(2) . . ?
N15 C11 N10 128.8(3) . . ?
N15 C11 N12 120.9(3) . . ?
N10 C11 N12 110.3(2) . . ?
N13 N12 C11 112.1(2) . . ?
N14 N13 N12 173.2(4) . . ?
C11 N15 N16 110.2(2) . . ?
C8 N16 N15 123.9(2) . . ?
C8 N16 C5 106.8(2) . . ?
N15 N16 C5 129.1(2) . . ?
N18 O17 H17 105(3) . . ?
O17 N18 H18A 109.5 . . ?
O17 N18 H18B 109.5 . . ?
H18A N18 H18B 109.5 . . ?
O17 N18 H18C 109.5 . . ?
H18A N18 H18C 109.5 . . ?
H18B N18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 N4 C5 -3.1(3) . . . . ?
O1 N3 N4 C5 176.3(2) . . . . ?
N3 N4 C5 N6 -7.2(4) . . . . ?
N3 N4 C5 N16 175.6(2) . . . . ?
N4 C5 N6 N7 -177.5(3) . . . . ?
N16 C5 N6 N7 -0.1(3) . . . . ?
C5 N6 N7 C8 0.3(3) . . . . ?
N6 N7 C8 N16 -0.3(3) . . . . ?
N6 N7 C8 N9 -179.9(3) . . . . ?
N7 C8 N9 N10 175.9(3) . . . . ?
N16 C8 N9 N10 -3.6(4) . . . . ?
C8 N9 N10 C11 -0.4(4) . . . . ?
N9 N10 C11 N15 4.3(4) . . . . ?
N9 N10 C11 N12 -175.7(2) . . . . ?
N15 C11 N12 N13 5.4(4) . . . . ?
N10 C11 N12 N13 -174.6(2) . . . . ?
N10 C11 N15 N16 -3.5(4) . . . . ?
N12 C11 N15 N16 176.6(2) . . . . ?
N7 C8 N16 N15 -175.1(2) . . . . ?
N9 C8 N16 N15 4.5(4) . . . . ?
N7 C8 N16 C5 0.3(3) . . . . ?
N9 C8 N16 C5 179.9(2) . . . . ?
C11 N15 N16 C8 -0.9(3) . . . . ?
C11 N15 N16 C5 -175.3(2) . . . . ?
N6 C5 N16 C8 -0.1(3) . . . . ?
N4 C5 N16 C8 177.8(2) . . . . ?
N6 C5 N16 N15 175.0(2) . . . . ?
N4 C5 N16 N15 -7.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N18 H18A O1 0.89 2.24 3.051(3) 150.8 .
N18 H18A O1 0.89 2.60 3.124(3) 118.8 2_646
N18 H18A O2 0.89 2.60 3.026(3) 110.4 2_656
N18 H18B O2 0.89 2.20 2.955(3) 142.9 2_646
N18 H18B N6 0.89 2.43 3.047(4) 126.8 1_455
N18 H18C N7 0.89 2.10 2.956(3) 160.9 1_465
O17 H17 N4 0.831(14) 2.03(2) 2.837(3) 163(5) .
O17 H17 N15 0.831(14) 2.73(4) 3.259(3) 123(4) .

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041


# start Validation Reply Form
_vrf_PLAT430_shrv747             
;
PROBLEM: Short Inter D...A Contact  O1       ..N3       .       2.85 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_shrv746
_database_code_depnum_ccdc_archive 'CCDC 1884783'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-08 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         'C3 H N8 O2, H4 N O'
_chemical_formula_sum            'C3 H5 N9 O3'
_chemical_formula_weight         215.16

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   16.224(2)
_cell_length_b                   5.5034(7)
_cell_length_c                   10.7701(13)
_cell_angle_alpha                90
_cell_angle_beta                 125.781(3)
_cell_angle_gamma                90
_cell_volume                     780.15(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1800
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      26.58

_exptl_crystal_description       block
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.160
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            4410
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.095
_diffrn_reflns_theta_max         30.068
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2145
_reflns_number_gt                1894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    0.990

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.2064P] 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         2145
_refine_ls_number_parameters     140
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.40676(19) 0.2572(4) 0.2588(3) 0.0443(6) Uani 1 1 d . . . . .
O2 O 0.29696(16) 0.5479(5) 0.1876(2) 0.0471(6) Uani 1 1 d . . . . .
N3 N 0.3802(2) 0.4559(5) 0.2833(3) 0.0315(5) Uani 1 1 d . . . . .
N4 N 0.45021(17) 0.5545(4) 0.4197(2) 0.0269(5) Uani 1 1 d . . . . .
C5 C 0.42303(19) 0.7611(5) 0.4566(3) 0.0220(5) Uani 1 1 d . . . . .
N6 N 0.33488(16) 0.8802(5) 0.3980(2) 0.0273(5) Uani 1 1 d . . . . .
N7 N 0.35220(16) 1.0794(5) 0.4859(3) 0.0277(5) Uani 1 1 d . . . . .
C8 C 0.45047(18) 1.0791(5) 0.5983(3) 0.0222(5) Uani 1 1 d . . . . .
N9 N 0.50412(18) 1.2392(4) 0.7151(3) 0.0287(5) Uani 1 1 d . . . . .
N10 N 0.60004(19) 1.1958(5) 0.8127(3) 0.0323(5) Uani 1 1 d . . . . .
C11 C 0.6431(2) 0.9948(5) 0.7931(3) 0.0309(6) Uani 1 1 d . . . . .
H11 H 0.7124 0.9725 0.8662 0.037 Uiso 1 1 calc R U . . .
N12 N 0.59738(16) 0.8337(4) 0.6837(2) 0.0265(5) Uani 1 1 d . . . . .
N13 N 0.49682(14) 0.8842(4) 0.5838(2) 0.0200(4) Uani 1 1 d . . . . .
O14 O 0.62488(19) 0.3150(5) 0.5336(3) 0.0521(7) Uani 1 1 d D . . . .
H14 H 0.580(3) 0.421(7) 0.504(6) 0.078 Uiso 1 1 d D U . . .
N15 N 0.70244(17) 0.4794(4) 0.5796(3) 0.0283(5) Uani 1 1 d . . . . .
H15A H 0.6858 0.5735 0.5009 0.042 Uiso 1 1 calc R U . . .
H15B H 0.7594 0.3991 0.6125 0.042 Uiso 1 1 calc R U . . .
H15C H 0.7119 0.5710 0.6551 0.042 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 1.258(3) . ?
O2 N3 1.231(4) . ?
N3 N4 1.338(3) . ?
N4 C5 1.360(3) . ?
C5 N6 1.348(4) . ?
C5 N13 1.360(3) . ?
N6 N7 1.367(3) . ?
N7 C8 1.323(3) . ?
C8 N9 1.355(3) . ?
C8 N13 1.370(3) . ?
N9 N10 1.293(3) . ?
N10 C11 1.389(4) . ?
C11 N12 1.305(4) . ?
C11 H11 0.9300 . ?
N12 N13 1.358(3) . ?
O14 N15 1.385(4) . ?
O14 H14 0.841(14) . ?
N15 H15A 0.8900 . ?
N15 H15B 0.8900 . ?
N15 H15C 0.8900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N3 O1 121.6(3) . . ?
O2 N3 N4 124.3(2) . . ?
O1 N3 N4 114.1(3) . . ?
N3 N4 C5 116.6(2) . . ?
N6 C5 N4 134.9(2) . . ?
N6 C5 N13 107.3(2) . . ?
N4 C5 N13 117.8(2) . . ?
C5 N6 N7 109.5(2) . . ?
C8 N7 N6 106.4(2) . . ?
N7 C8 N9 128.7(2) . . ?
N7 C8 N13 110.2(2) . . ?
N9 C8 N13 121.2(2) . . ?
N10 N9 C8 116.7(2) . . ?
N9 N10 C11 119.8(2) . . ?
N12 C11 N10 127.4(3) . . ?
N12 C11 H11 116.3 . . ?
N10 C11 H11 116.3 . . ?
C11 N12 N13 111.2(2) . . ?
N12 N13 C5 129.6(2) . . ?
N12 N13 C8 123.7(2) . . ?
C5 N13 C8 106.62(19) . . ?
N15 O14 H14 95(4) . . ?
O14 N15 H15A 109.5 . . ?
O14 N15 H15B 109.5 . . ?
H15A N15 H15B 109.5 . . ?
O14 N15 H15C 109.5 . . ?
H15A N15 H15C 109.5 . . ?
H15B N15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 N4 C5 4.8(4) . . . . ?
O1 N3 N4 C5 -175.8(2) . . . . ?
N3 N4 C5 N6 11.8(4) . . . . ?
N3 N4 C5 N13 -170.7(2) . . . . ?
N4 C5 N6 N7 178.2(3) . . . . ?
N13 C5 N6 N7 0.6(3) . . . . ?
C5 N6 N7 C8 -0.6(3) . . . . ?
N6 N7 C8 N9 -179.7(3) . . . . ?
N6 N7 C8 N13 0.3(3) . . . . ?
N7 C8 N9 N10 178.8(3) . . . . ?
N13 C8 N9 N10 -1.3(4) . . . . ?
C8 N9 N10 C11 0.9(4) . . . . ?
N9 N10 C11 N12 -0.4(5) . . . . ?
N10 C11 N12 N13 0.1(4) . . . . ?
C11 N12 N13 C5 -179.1(3) . . . . ?
C11 N12 N13 C8 -0.5(3) . . . . ?
N6 C5 N13 N12 178.5(2) . . . . ?
N4 C5 N13 N12 0.4(4) . . . . ?
N6 C5 N13 C8 -0.4(3) . . . . ?
N4 C5 N13 C8 -178.5(2) . . . . ?
N7 C8 N13 N12 -178.9(2) . . . . ?
N9 C8 N13 N12 1.1(4) . . . . ?
N7 C8 N13 C5 0.0(3) . . . . ?
N9 C8 N13 C5 -180.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 N6 0.93 2.65 3.333(4) 130.5 4_565
O14 H14 N3 0.841(14) 2.68(4) 3.333(4) 136(5) .
O14 H14 N4 0.841(14) 1.88(2) 2.685(3) 159(5) .
N15 H15A N10 0.89 2.09 2.939(3) 159.6 2_574
N15 H15B O1 0.89 2.13 2.988(3) 161.9 4
N15 H15B O2 0.89 2.55 3.168(3) 127.2 4
N15 H15B N3 0.89 2.61 3.387(3) 145.9 4
N15 H15C O2 0.89 2.42 2.896(4) 113.8 4_565
N15 H15C N6 0.89 2.19 2.890(3) 135.3 4_565
N15 H15C N12 0.89 2.51 3.194(3) 133.9 .

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_shrv752
_database_code_depnum_ccdc_archive 'CCDC 1884785'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-08 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         'C3 H2 N10'
_chemical_formula_sum            'C3 H2 N10'
_chemical_formula_weight         178.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.5258(4)
_cell_length_b                   6.7155(5)
_cell_length_c                   18.0885(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     671.24(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3848
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      30.06

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.195
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            7923
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.252
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1927
_reflns_number_gt                1737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.998

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.0626P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1927
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.1137(4) 0.6596(3) 0.48493(9) 0.0573(5) Uani 1 1 d . . . . .
N2 N 0.0610(3) 0.6622(2) 0.42551(7) 0.0367(3) Uani 1 1 d . . . . .
N3 N -0.0313(3) 0.6524(2) 0.36239(7) 0.0347(3) Uani 1 1 d . . . . .
C4 C 0.1183(3) 0.71168(19) 0.30491(8) 0.0260(3) Uani 1 1 d . . . . .
N5 N 0.0372(2) 0.66874(18) 0.23925(6) 0.0266(3) Uani 1 1 d . . . . .
N6 N 0.1971(2) 0.73151(17) 0.18677(6) 0.0253(3) Uani 1 1 d . . . . .
C7 C 0.1852(3) 0.7158(2) 0.11237(8) 0.0285(3) Uani 1 1 d . . . . .
N8 N -0.0020(3) 0.6336(2) 0.07614(8) 0.0370(3) Uani 1 1 d . . . . .
H8A H -0.003(4) 0.656(3) 0.0271(14) 0.055 Uiso 1 1 d . U . . .
H8B H -0.138(5) 0.639(3) 0.0999(12) 0.055 Uiso 1 1 d . U . . .
N9 N 0.3901(3) 0.7899(2) 0.08414(7) 0.0367(3) Uani 1 1 d . . . . .
N10 N 0.5346(3) 0.8574(2) 0.14059(8) 0.0382(3) Uani 1 1 d . . . . .
C11 C 0.4149(3) 0.8216(2) 0.20222(8) 0.0298(3) Uani 1 1 d . . . . .
N12 N 0.4785(3) 0.8664(2) 0.27240(7) 0.0332(3) Uani 1 1 d . . . . .
N13 N 0.3313(2) 0.81315(19) 0.32434(7) 0.0316(3) 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
N1 N2 1.1136(19) . ?
N2 N3 1.2524(18) . ?
N3 C4 1.3868(19) . ?
C4 N5 1.3017(18) . ?
C4 N13 1.4047(19) . ?
N5 N6 1.3635(16) . ?
N6 C7 1.3515(18) . ?
N6 C11 1.3759(19) . ?
C7 N9 1.338(2) . ?
C7 N8 1.343(2) . ?
N8 H8A 0.90(3) . ?
N8 H8B 0.87(3) . ?
N9 N10 1.373(2) . ?
N10 C11 1.318(2) . ?
C11 N12 1.351(2) . ?
N12 N13 1.2932(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 N3 170.25(19) . . ?
N2 N3 C4 115.18(14) . . ?
N5 C4 N3 114.53(13) . . ?
N5 C4 N13 128.63(13) . . ?
N3 C4 N13 116.82(12) . . ?
C4 N5 N6 110.10(12) . . ?
C7 N6 N5 129.60(13) . . ?
C7 N6 C11 106.21(12) . . ?
N5 N6 C11 124.15(12) . . ?
N9 C7 N8 128.18(14) . . ?
N9 C7 N6 108.04(13) . . ?
N8 C7 N6 123.76(14) . . ?
C7 N8 H8A 114.9(16) . . ?
C7 N8 H8B 114.2(15) . . ?
H8A N8 H8B 118(2) . . ?
C7 N9 N10 109.33(12) . . ?
C11 N10 N9 106.07(13) . . ?
N10 C11 N12 128.57(15) . . ?
N10 C11 N6 110.33(13) . . ?
N12 C11 N6 121.08(13) . . ?
N13 N12 C11 117.23(13) . . ?
N12 N13 C4 118.64(12) . . ?

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
N2 N3 C4 N5 168.62(13) . . . . ?
N2 N3 C4 N13 -12.95(19) . . . . ?
N3 C4 N5 N6 -179.59(12) . . . . ?
N13 C4 N5 N6 2.20(19) . . . . ?
C4 N5 N6 C7 179.46(14) . . . . ?
C4 N5 N6 C11 1.76(18) . . . . ?
N5 N6 C7 N9 -176.84(13) . . . . ?
C11 N6 C7 N9 1.17(16) . . . . ?
N5 N6 C7 N8 1.6(2) . . . . ?
C11 N6 C7 N8 179.58(14) . . . . ?
N8 C7 N9 N10 -179.31(15) . . . . ?
N6 C7 N9 N10 -1.00(16) . . . . ?
C7 N9 N10 C11 0.40(17) . . . . ?
N9 N10 C11 N12 -177.82(15) . . . . ?
N9 N10 C11 N6 0.35(17) . . . . ?
C7 N6 C11 N10 -0.95(16) . . . . ?
N5 N6 C11 N10 177.20(13) . . . . ?
C7 N6 C11 N12 177.38(14) . . . . ?
N5 N6 C11 N12 -4.5(2) . . . . ?
N10 C11 N12 N13 -179.04(15) . . . . ?
N6 C11 N12 N13 3.0(2) . . . . ?
C11 N12 N13 C4 0.6(2) . . . . ?
N5 C4 N13 N12 -3.6(2) . . . . ?
N3 C4 N13 N12 178.27(13) . . . . ?

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
N8 H8A N9 0.90(3) 2.13(3) 3.0041(19) 164(2) 4_465
N8 H8B N10 0.87(3) 2.44(3) 3.190(2) 145(2) 1_455

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_shrv742b
_database_code_depnum_ccdc_archive 'CCDC 1884780'
loop_
_audit_author_name
_audit_author_address
'Gregory Imler'
;Naval Research Laboratory
United States of America
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-03-08 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         ?
_chemical_formula_sum            'C3 H N11 O2'
_chemical_formula_weight         223.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.5608(5)
_cell_length_b                   18.9684(18)
_cell_length_c                   7.5833(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.458(2)
_cell_angle_gamma                90
_cell_volume                     799.86(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3996
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      27.63

_exptl_crystal_description       block
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.052
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            9411
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         29.898
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             4137
_reflns_number_gt                3652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_max     0.800
_reflns_Friedel_fraction_full    0.910

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.3454P] 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_abs_structure_details 
;
 Flack x determined using 1414 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4137
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
O1 O 1.1686(6) 0.43788(17) 0.4956(4) 0.0536(8) Uani 1 1 d . . . . .
O2 O 0.9044(5) 0.47099(15) 0.6860(4) 0.0471(7) Uani 1 1 d . . . . .
N3 N 0.9918(6) 0.42549(15) 0.5862(4) 0.0368(6) Uani 1 1 d . . . . .
N4 N 0.8952(5) 0.36044(16) 0.5736(4) 0.0364(7) Uani 1 1 d . . . . .
C5 C 0.6976(6) 0.35009(17) 0.6680(4) 0.0298(6) Uani 1 1 d . . . . .
N6 N 0.5475(5) 0.39049(17) 0.7623(4) 0.0376(7) Uani 1 1 d . . . . .
H6 H 0.5701 0.4349 0.7779 0.045 Uiso 1 1 calc R U . . .
N7 N 0.3563(5) 0.35524(17) 0.8310(4) 0.0397(7) Uani 1 1 d . . . . .
C8 C 0.3932(6) 0.29037(19) 0.7769(4) 0.0306(6) Uani 1 1 d . . . . .
N9 N 0.2464(5) 0.23364(17) 0.8039(4) 0.0375(7) Uani 1 1 d . . . . .
N10 N 0.3132(6) 0.17486(16) 0.7393(4) 0.0372(7) Uani 1 1 d . . . . .
C11 C 0.5367(6) 0.17153(19) 0.6510(5) 0.0322(7) Uani 1 1 d . . . . .
N12 N 0.6122(6) 0.10600(17) 0.5990(5) 0.0429(7) Uani 1 1 d . . . . .
N13 N 0.4676(6) 0.05637(18) 0.6259(4) 0.0428(7) Uani 1 1 d . . . . .
N14 N 0.3650(8) 0.0066(2) 0.6394(6) 0.0593(10) Uani 1 1 d . . . . .
N15 N 0.6813(5) 0.22305(15) 0.6118(4) 0.0320(6) Uani 1 1 d . . . . .
N16 N 0.5968(5) 0.28510(15) 0.6785(3) 0.0283(5) Uani 1 1 d . . . . .
O17 O 0.6763(5) 0.56186(17) 0.9811(4) 0.0514(7) Uani 1 1 d . . . . .
O18 O 0.4056(5) 0.53112(14) 0.7884(4) 0.0464(7) Uani 1 1 d . . . . .
N19 N 0.4953(5) 0.57466(16) 0.8936(4) 0.0361(6) Uani 1 1 d . . . . .
N20 N 0.3991(5) 0.63940(16) 0.9138(4) 0.0349(6) Uani 1 1 d . . . . .
C21 C 0.1975(6) 0.65049(18) 0.8186(4) 0.0291(6) Uani 1 1 d . . . . .
N22 N 0.0471(5) 0.61196(16) 0.7179(4) 0.0358(6) Uani 1 1 d . . . . .
H22 H 0.0712 0.5681 0.6958 0.043 Uiso 1 1 calc R U . . .
N23 N -0.1460(5) 0.64784(17) 0.6538(4) 0.0380(7) Uani 1 1 d . . . . .
C24 C -0.1122(6) 0.71145(19) 0.7179(4) 0.0317(7) Uani 1 1 d . . . . .
N25 N -0.2629(5) 0.76801(17) 0.6996(4) 0.0374(7) Uani 1 1 d . . . . .
N26 N -0.1953(5) 0.82564(17) 0.7718(4) 0.0352(6) Uani 1 1 d . . . . .
C27 C 0.0310(6) 0.82799(18) 0.8594(4) 0.0302(6) Uani 1 1 d . . . . .
N28 N 0.1059(6) 0.89301(18) 0.9199(5) 0.0417(7) Uani 1 1 d . . . . .
N29 N -0.0395(6) 0.94285(18) 0.8971(5) 0.0421(7) Uani 1 1 d . . . . .
N30 N -0.1432(8) 0.9929(2) 0.8869(6) 0.0611(10) Uani 1 1 d . . . . .
N31 N 0.1781(5) 0.77627(14) 0.8917(4) 0.0310(6) Uani 1 1 d . . . . .
N32 N 0.0943(4) 0.71553(14) 0.8164(3) 0.0278(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.227(4) . ?
O2 N3 1.249(4) . ?
N3 N4 1.349(4) . ?
N4 C5 1.331(4) . ?
C5 N6 1.343(4) . ?
C5 N16 1.357(4) . ?
N6 N7 1.363(4) . ?
N6 H6 0.8600 . ?
N7 C8 1.314(5) . ?
C8 N16 1.364(4) . ?
C8 N9 1.367(5) . ?
N9 N10 1.274(4) . ?
N10 C11 1.418(5) . ?
C11 N15 1.301(5) . ?
C11 N12 1.371(5) . ?
N12 N13 1.256(5) . ?
N13 N14 1.109(5) . ?
N15 N16 1.366(4) . ?
O17 N19 1.225(4) . ?
O18 N19 1.249(4) . ?
N19 N20 1.349(4) . ?
N20 C21 1.345(4) . ?
C21 N22 1.344(4) . ?
C21 N32 1.361(4) . ?
N22 N23 1.358(4) . ?
N22 H22 0.8600 . ?
N23 C24 1.314(5) . ?
C24 N32 1.367(4) . ?
C24 N25 1.368(5) . ?
N25 N26 1.278(4) . ?
N26 C27 1.419(4) . ?
C27 N31 1.300(4) . ?
C27 N28 1.379(5) . ?
N28 N29 1.255(5) . ?
N29 N30 1.112(5) . ?
N31 N32 1.366(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 121.7(3) . . ?
O1 N3 N4 117.1(3) . . ?
O2 N3 N4 121.2(3) . . ?
C5 N4 N3 115.3(3) . . ?
N4 C5 N6 136.2(3) . . ?
N4 C5 N16 120.6(3) . . ?
N6 C5 N16 103.2(3) . . ?
C5 N6 N7 114.4(3) . . ?
C5 N6 H6 122.8 . . ?
N7 N6 H6 122.8 . . ?
C8 N7 N6 102.4(3) . . ?
N7 C8 N16 111.8(3) . . ?
N7 C8 N9 126.5(3) . . ?
N16 C8 N9 121.6(3) . . ?
N10 N9 C8 117.0(3) . . ?
N9 N10 C11 118.7(3) . . ?
N15 C11 N12 115.1(3) . . ?
N15 C11 N10 128.3(3) . . ?
N12 C11 N10 116.6(3) . . ?
N13 N12 C11 115.8(3) . . ?
N14 N13 N12 169.8(4) . . ?
C11 N15 N16 110.3(3) . . ?
C5 N16 C8 108.1(3) . . ?
C5 N16 N15 128.1(3) . . ?
C8 N16 N15 123.7(3) . . ?
O17 N19 O18 122.5(3) . . ?
O17 N19 N20 116.3(3) . . ?
O18 N19 N20 121.2(3) . . ?
C21 N20 N19 114.3(3) . . ?
N22 C21 N20 137.1(3) . . ?
N22 C21 N32 103.0(3) . . ?
N20 C21 N32 119.9(3) . . ?
C21 N22 N23 114.7(3) . . ?
C21 N22 H22 122.7 . . ?
N23 N22 H22 122.7 . . ?
C24 N23 N22 102.6(3) . . ?
N23 C24 N32 111.8(3) . . ?
N23 C24 N25 126.7(3) . . ?
N32 C24 N25 121.5(3) . . ?
N26 N25 C24 116.7(3) . . ?
N25 N26 C27 119.0(3) . . ?
N31 C27 N28 115.1(3) . . ?
N31 C27 N26 128.3(3) . . ?
N28 C27 N26 116.6(3) . . ?
N29 N28 C27 115.8(3) . . ?
N30 N29 N28 170.0(4) . . ?
C27 N31 N32 110.2(3) . . ?
C21 N32 N31 128.1(3) . . ?
C21 N32 C24 107.9(3) . . ?
N31 N32 C24 124.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 N4 C5 -177.2(3) . . . . ?
O2 N3 N4 C5 2.8(5) . . . . ?
N3 N4 C5 N6 8.9(6) . . . . ?
N3 N4 C5 N16 -174.0(3) . . . . ?
N4 C5 N6 N7 176.9(4) . . . . ?
N16 C5 N6 N7 -0.4(4) . . . . ?
C5 N6 N7 C8 0.4(4) . . . . ?
N6 N7 C8 N16 -0.2(4) . . . . ?
N6 N7 C8 N9 -177.1(3) . . . . ?
N7 C8 N9 N10 179.4(4) . . . . ?
N16 C8 N9 N10 2.8(5) . . . . ?
C8 N9 N10 C11 2.5(5) . . . . ?
N9 N10 C11 N15 -6.4(5) . . . . ?
N9 N10 C11 N12 173.8(3) . . . . ?
N15 C11 N12 N13 -175.7(3) . . . . ?
N10 C11 N12 N13 4.2(5) . . . . ?
C11 N12 N13 N14 -179(2) . . . . ?
N12 C11 N15 N16 -176.3(3) . . . . ?
N10 C11 N15 N16 3.9(5) . . . . ?
N4 C5 N16 C8 -177.6(3) . . . . ?
N6 C5 N16 C8 0.3(3) . . . . ?
N4 C5 N16 N15 5.1(5) . . . . ?
N6 C5 N16 N15 -177.1(3) . . . . ?
N7 C8 N16 C5 0.0(4) . . . . ?
N9 C8 N16 C5 177.0(3) . . . . ?
N7 C8 N16 N15 177.4(3) . . . . ?
N9 C8 N16 N15 -5.5(5) . . . . ?
C11 N15 N16 C5 179.0(3) . . . . ?
C11 N15 N16 C8 2.0(4) . . . . ?
O17 N19 N20 C21 -178.4(3) . . . . ?
O18 N19 N20 C21 2.9(5) . . . . ?
N19 N20 C21 N22 8.0(6) . . . . ?
N19 N20 C21 N32 -174.6(3) . . . . ?
N20 C21 N22 N23 176.9(4) . . . . ?
N32 C21 N22 N23 -0.8(4) . . . . ?
C21 N22 N23 C24 0.1(4) . . . . ?
N22 N23 C24 N32 0.6(4) . . . . ?
N22 N23 C24 N25 -176.7(3) . . . . ?
N23 C24 N25 N26 -179.6(4) . . . . ?
N32 C24 N25 N26 3.3(5) . . . . ?
C24 N25 N26 C27 2.1(5) . . . . ?
N25 N26 C27 N31 -6.7(5) . . . . ?
N25 N26 C27 N28 173.8(3) . . . . ?
N31 C27 N28 N29 -176.7(3) . . . . ?
N26 C27 N28 N29 2.8(5) . . . . ?
N28 C27 N31 N32 -176.0(3) . . . . ?
N26 C27 N31 N32 4.5(5) . . . . ?
N22 C21 N32 N31 -176.8(3) . . . . ?
N20 C21 N32 N31 5.0(5) . . . . ?
N22 C21 N32 C24 1.1(3) . . . . ?
N20 C21 N32 C24 -177.1(3) . . . . ?
C27 N31 N32 C21 179.2(3) . . . . ?
C27 N31 N32 C24 1.6(4) . . . . ?
N23 C24 N32 C21 -1.1(4) . . . . ?
N25 C24 N32 C21 176.3(3) . . . . ?
N23 C24 N32 N31 176.9(3) . . . . ?
N25 C24 N32 N31 -5.6(5) . . . . ?

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
N6 H6 O2 0.86 2.10 2.574(4) 113.7 .
N6 H6 O18 0.86 2.04 2.789(4) 144.6 .
N22 H22 O2 0.86 2.06 2.799(4) 143.2 1_455
N22 H22 O18 0.86 2.10 2.568(4) 113.4 .

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050


# start Validation Reply Form
_vrf_PLAT112_shrv742b            
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem        21        100 %Fit  
RESPONSE: This crystal displays pseudosymmetry.
;
# end Validation Reply Form
