# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
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data_mo_dm15092_0m
_database_code_depnum_ccdc_archive 'CCDC 1058871'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_audit_creation_date             2015-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            2,2,2-trinitroethyl
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C3 H3 N5 O10), H2 O'
_chemical_formula_sum            'C6 H8 N10 O21'
_chemical_formula_weight         556.22
_chemical_melting_point          109oC
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8667(11)
_cell_length_b                   12.1727(13)
_cell_length_c                   15.0448(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.473(2)
_cell_angle_gamma                90
_cell_volume                     1989.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4010
_cell_measurement_temperature    130
_cell_measurement_theta_max      27.500
_cell_measurement_theta_min      2.513
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0716 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.7601.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20071
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.930
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4295
_reflns_number_total             6219
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6219
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.3844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N6-O11 = N6-O12 = N7-O13 = N7-O14 = N8-O15 = N8-O16
 1.22 with sigma of 0.01
 N6'-O11' = N6'-O12' = N7'-O13' = N7'-O14' = N8'-O15' = N8'-O16'
 1.22 with sigma of 0.01
3. Others
 Fixed Sof: N6(0.75) O11(0.75) O12(0.75) N7(0.75) O13(0.75) O14(0.75) N8(0.75)
 O15(0.75) O16(0.75) N6'(0.25) O11'(0.25) O12'(0.25) N7'(0.25) O13'(0.25)
 O14'(0.25) N8'(0.25) O15'(0.25) O16'(0.25)
4.a Free rotating group:
 O1S(H1SA,H1SB)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B)
4.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.41279(14) 0.55574(14) -0.05901(10) 0.0521(4) Uani 1 1 d . . . . .
O2 O 0.41605(15) 0.40560(12) -0.13286(10) 0.0491(4) Uani 1 1 d . . . . .
O3 O 0.65249(12) 0.40957(11) -0.24044(8) 0.0332(3) Uani 1 1 d . . . . .
O4 O 0.49108(12) 0.46467(13) -0.31659(8) 0.0414(3) Uani 1 1 d . . . . .
O5 O 0.36157(13) 0.64914(15) -0.22564(13) 0.0665(5) Uani 1 1 d . . . . .
O6 O 0.54063(13) 0.71071(12) -0.26195(9) 0.0431(3) Uani 1 1 d . . . . .
O7 O 0.62947(9) 0.67238(10) -0.07743(7) 0.0251(2) Uani 1 1 d . . . . .
O8 O 0.82838(10) 0.66700(10) -0.03226(8) 0.0283(3) Uani 1 1 d . . . . .
O9 O 0.87606(10) 0.83585(11) 0.07620(7) 0.0299(3) Uani 1 1 d . . . . .
O10 O 0.71530(11) 0.92124(11) 0.12156(9) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.44627(12) 0.49810(12) -0.11876(9) 0.0271(3) Uani 1 1 d . . . . .
N2 N 0.56273(12) 0.46646(12) -0.25361(8) 0.0259(3) Uani 1 1 d . . . . .
N3 N 0.47278(14) 0.64652(13) -0.22678(10) 0.0334(3) Uani 1 1 d . . . . .
N4 N 0.68851(11) 0.79374(11) 0.02135(8) 0.0236(3) Uani 1 1 d . . . . .
H4 H 0.6101 0.8118 0.0183 0.028 Uiso 1 1 calc R . . . .
N5 N 0.76622(11) 0.85291(11) 0.07640(8) 0.0226(3) Uani 1 1 d . . . . .
C1 C 0.53715(13) 0.55060(13) -0.18126(9) 0.0210(3) Uani 1 1 d . . . . .
C2 C 0.65694(13) 0.58266(13) -0.13484(10) 0.0240(3) Uani 1 1 d . . . . .
H2A H 0.6907 0.5201 -0.1000 0.029 Uiso 1 1 calc R . . . .
H2B H 0.7183 0.6051 -0.1789 0.029 Uiso 1 1 calc R . . . .
C3 C 0.72842(13) 0.70711(13) -0.02930(9) 0.0213(3) Uani 1 1 d . . . . .
O17 O 0.96949(10) 0.17176(10) 0.12311(7) 0.0258(2) Uani 1 1 d . . . . .
O18 O 0.76887(10) 0.17473(11) 0.08141(8) 0.0325(3) Uani 1 1 d . . . . .
O19 O 0.73502(10) 0.31586(12) -0.05275(8) 0.0365(3) Uani 1 1 d . . . . .
O20 O 0.90115(12) 0.39576(12) -0.09650(8) 0.0382(3) Uani 1 1 d . . . . .
N6 N 1.05602(15) -0.03176(15) 0.29424(10) 0.0205(3) Uani 0.75 1 d D . P A 1
O11 O 1.1422(2) -0.0297(2) 0.34641(14) 0.0336(5) Uani 0.75 1 d D . P A 1
O12 O 0.9639(6) -0.0875(9) 0.3002(6) 0.0322(14) Uani 0.75 1 d D . P A 1
N7 N 1.10520(18) -0.04580(18) 0.13847(12) 0.0243(4) Uani 0.75 1 d D . P A 1
O13 O 1.14013(18) -0.13458(16) 0.16215(12) 0.0371(4) Uani 0.75 1 d D . P A 1
O14 O 1.0993(8) -0.0110(8) 0.0632(3) 0.0424(15) Uani 0.75 1 d D . P A 1
N8 N 1.16411(16) 0.12103(18) 0.22286(12) 0.0223(3) Uani 0.75 1 d D . P A 1
O15 O 1.25493(17) 0.11479(19) 0.17846(14) 0.0381(5) Uani 0.75 1 d D . P A 1
O16 O 1.1424(6) 0.1905(3) 0.2792(5) 0.0365(11) Uani 0.75 1 d D . P A 1
N6' N 1.0353(6) -0.0892(5) 0.2410(4) 0.0376(14) Uani 0.25 1 d D . P A 2
O11' O 1.1078(6) -0.1606(5) 0.2170(5) 0.0508(16) Uani 0.25 1 d D . P A 2
O12' O 0.9449(17) -0.087(3) 0.2874(17) 0.031(4) Uani 0.25 1 d D . P A 2
N7' N 1.1429(6) 0.0134(7) 0.1270(5) 0.0428(16) Uani 0.25 1 d D . P A 2
O13' O 1.2449(5) 0.0588(8) 0.1356(6) 0.069(2) Uani 0.25 1 d D . P A 2
O14' O 1.095(2) -0.029(2) 0.0618(11) 0.038(4) Uani 0.25 1 d D . P A 2
N8' N 1.1354(6) 0.0833(6) 0.2800(5) 0.0486(18) Uani 0.25 1 d D . P A 2
O15' O 1.1758(7) 0.0240(7) 0.3402(4) 0.051(2) Uani 0.25 1 d D . P A 2
O16' O 1.140(2) 0.1823(10) 0.2667(17) 0.055(5) Uani 0.25 1 d D . P A 2
N9 N 0.91722(12) 0.27920(11) 0.01310(8) 0.0242(3) Uani 1 1 d . . . . .
H9 H 0.9968 0.2927 0.0147 0.029 Uiso 1 1 calc R . . . .
N10 N 0.84463(12) 0.33327(12) -0.04918(8) 0.0253(3) Uani 1 1 d . . . . .
C4 C 1.06323(13) 0.03304(13) 0.20916(9) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.94176(13) 0.08864(13) 0.18636(10) 0.0227(3) Uani 1 1 d . . . . .
H5A H 0.8822 0.0352 0.1605 0.027 Uiso 1 1 calc R . . . .
H5B H 0.9062 0.1215 0.2401 0.027 Uiso 1 1 calc R . . . .
C6 C 0.87150(13) 0.20514(13) 0.07299(9) 0.0204(3) Uani 1 1 d . . . . .
O1S O 0.53996(12) 0.12442(13) -0.00840(10) 0.0428(3) Uani 1 1 d . . . . .
H1SA H 0.5669 0.1546 -0.0550 0.064 Uiso 1 1 d G . . . .
H1SB H 0.5930 0.1312 0.0338 0.064 Uiso 1 1 d G . . . .


_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 N1 1.2040(19) . ?
O2 N1 1.1904(19) . ?
O3 N2 1.2084(19) . ?
O4 N2 1.2111(17) . ?
O5 N3 1.209(2) . ?
O6 N3 1.206(2) . ?
O7 C2 1.4287(18) . ?
O7 C3 1.3488(17) . ?
O8 C3 1.1928(18) . ?
O9 N5 1.2116(16) . ?
O10 N5 1.2161(18) . ?
N1 C1 1.522(2) . ?
N2 C1 1.525(2) . ?
N3 C1 1.516(2) . ?
N4 H4 0.8800 . ?
N4 N5 1.3718(17) . ?
N4 C3 1.378(2) . ?
C1 C2 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O17 C5 1.4265(18) . ?
O17 C6 1.3514(16) . ?
O18 C6 1.1849(18) . ?
O19 N10 1.2096(17) . ?
O20 N10 1.2187(18) . ?
N6 O11 1.206(3) . ?
N6 O12 1.215(7) . ?
N6 C4 1.507(2) . ?
N7 O13 1.197(3) . ?
N7 O14 1.209(6) . ?
N7 C4 1.512(2) . ?
N8 O15 1.208(3) . ?
N8 O16 1.225(6) . ?
N8 C4 1.543(2) . ?
N6' O11' 1.233(7) . ?
N6' O12' 1.220(10) . ?
N6' C4 1.594(7) . ?
N7' O13' 1.242(8) . ?
N7' O14' 1.215(10) . ?
N7' C4 1.545(8) . ?
N8' O15' 1.230(7) . ?
N8' O16' 1.223(10) . ?
N8' C4 1.444(7) . ?
N9 H9 0.8800 . ?
N9 N10 1.3768(17) . ?
N9 C6 1.376(2) . ?
C4 C5 1.515(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O1S H1SA 0.8500 . ?
O1S H1SB 0.8504 . ?

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
C3 O7 C2 112.84(11) . . ?
O1 N1 C1 115.46(14) . . ?
O2 N1 O1 126.66(15) . . ?
O2 N1 C1 117.88(13) . . ?
O3 N2 O4 128.16(15) . . ?
O3 N2 C1 115.40(12) . . ?
O4 N2 C1 116.43(14) . . ?
O5 N3 O6 127.70(16) . . ?
O5 N3 C1 117.62(15) . . ?
O6 N3 C1 114.65(14) . . ?
N5 N4 H4 118.7 . . ?
N5 N4 C3 122.57(12) . . ?
C3 N4 H4 118.7 . . ?
O9 N5 O10 125.52(13) . . ?
O9 N5 N4 119.98(13) . . ?
O10 N5 N4 114.49(12) . . ?
N1 C1 N2 106.98(12) . . ?
N3 C1 N1 107.67(12) . . ?
N3 C1 N2 106.58(12) . . ?
C2 C1 N1 112.80(12) . . ?
C2 C1 N2 109.40(12) . . ?
C2 C1 N3 113.05(13) . . ?
O7 C2 C1 106.60(12) . . ?
O7 C2 H2A 110.4 . . ?
O7 C2 H2B 110.4 . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O7 C3 N4 106.20(12) . . ?
O8 C3 O7 124.46(14) . . ?
O8 C3 N4 129.33(13) . . ?
C6 O17 C5 114.11(11) . . ?
O11 N6 O12 126.2(5) . . ?
O11 N6 C4 119.05(17) . . ?
O12 N6 C4 114.6(5) . . ?
O13 N7 O14 127.1(5) . . ?
O13 N7 C4 117.58(17) . . ?
O14 N7 C4 115.3(5) . . ?
O15 N8 O16 126.9(3) . . ?
O15 N8 C4 118.05(19) . . ?
O16 N8 C4 115.0(3) . . ?
O11' N6' C4 116.2(6) . . ?
O12' N6' O11' 135.5(17) . . ?
O12' N6' C4 108.2(16) . . ?
O13' N7' C4 111.4(7) . . ?
O14' N7' O13' 129.6(14) . . ?
O14' N7' C4 118.2(12) . . ?
O15' N8' C4 118.1(7) . . ?
O16' N8' O15' 133.2(15) . . ?
O16' N8' C4 108.7(14) . . ?
N10 N9 H9 118.4 . . ?
N10 N9 C6 123.26(12) . . ?
C6 N9 H9 118.4 . . ?
O19 N10 O20 126.43(13) . . ?
O19 N10 N9 119.53(13) . . ?
O20 N10 N9 114.04(13) . . ?
N6 C4 N7 106.77(14) . . ?
N6 C4 N8 107.59(12) . . ?
N6 C4 C5 111.23(12) . . ?
N7 C4 N8 107.97(14) . . ?
N7 C4 C5 113.65(13) . . ?
N7' C4 N6' 102.2(4) . . ?
N8' C4 N6' 106.1(4) . . ?
N8' C4 N7' 110.5(4) . . ?
N8' C4 C5 115.6(3) . . ?
C5 C4 N8 109.40(13) . . ?
C5 C4 N6' 108.3(2) . . ?
C5 C4 N7' 113.0(3) . . ?
O17 C5 C4 105.68(12) . . ?
O17 C5 H5A 110.6 . . ?
O17 C5 H5B 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
O17 C6 N9 105.64(12) . . ?
O18 C6 O17 125.22(14) . . ?
O18 C6 N9 129.14(13) . . ?
H1SA O1S H1SB 109.5 . . ?

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
N4 H4 O1S 0.88 1.81 2.6776(18) 168.9 3_665
N9 H9 O8 0.88 1.97 2.8483(17) 172.8 3_765

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 N1 C1 N2 -177.50(14) . . . . ?
O1 N1 C1 N3 -63.27(17) . . . . ?
O1 N1 C1 C2 62.16(19) . . . . ?
O2 N1 C1 N2 2.91(19) . . . . ?
O2 N1 C1 N3 117.14(17) . . . . ?
O2 N1 C1 C2 -117.43(17) . . . . ?
O3 N2 C1 N1 -94.42(15) . . . . ?
O3 N2 C1 N3 150.62(14) . . . . ?
O3 N2 C1 C2 28.07(18) . . . . ?
O4 N2 C1 N1 85.42(16) . . . . ?
O4 N2 C1 N3 -29.54(18) . . . . ?
O4 N2 C1 C2 -152.09(14) . . . . ?
O5 N3 C1 N1 -18.0(2) . . . . ?
O5 N3 C1 N2 96.49(19) . . . . ?
O5 N3 C1 C2 -143.28(17) . . . . ?
O6 N3 C1 N1 163.55(14) . . . . ?
O6 N3 C1 N2 -81.96(17) . . . . ?
O6 N3 C1 C2 38.3(2) . . . . ?
N1 C1 C2 O7 -69.30(16) . . . . ?
N2 C1 C2 O7 171.76(12) . . . . ?
N3 C1 C2 O7 53.16(17) . . . . ?
N5 N4 C3 O7 -177.27(13) . . . . ?
N5 N4 C3 O8 3.2(3) . . . . ?
C2 O7 C3 O8 -1.3(2) . . . . ?
C2 O7 C3 N4 179.22(13) . . . . ?
C3 O7 C2 C1 177.93(12) . . . . ?
C3 N4 N5 O9 6.3(2) . . . . ?
C3 N4 N5 O10 -174.70(14) . . . . ?
N6 C4 C5 O17 162.58(12) . . . . ?
O11 N6 C4 N7 96.0(2) . . . . ?
O11 N6 C4 N8 -19.7(2) . . . . ?
O11 N6 C4 N6' 126.8(4) . . . . ?
O11 N6 C4 N7' 70.1(4) . . . . ?
O11 N6 C4 N8' -29.3(4) . . . . ?
O11 N6 C4 C5 -139.5(2) . . . . ?
O12 N6 C4 N7 -79.5(5) . . . . ?
O12 N6 C4 N8 164.8(5) . . . . ?
O12 N6 C4 N6' -48.6(6) . . . . ?
O12 N6 C4 N7' -105.4(6) . . . . ?
O12 N6 C4 N8' 155.2(6) . . . . ?
O12 N6 C4 C5 45.0(5) . . . . ?
N7 C4 C5 O17 -76.88(17) . . . . ?
O13 N7 C4 N6 -9.9(2) . . . . ?
O13 N7 C4 N8 105.5(2) . . . . ?
O13 N7 C4 N6' -30.6(3) . . . . ?
O13 N7 C4 N7' 131.0(6) . . . . ?
O13 N7 C4 N8' 65.7(5) . . . . ?
O13 N7 C4 C5 -132.93(19) . . . . ?
O14 N7 C4 N6 170.0(4) . . . . ?
O14 N7 C4 N8 -74.5(4) . . . . ?
O14 N7 C4 N6' 149.4(5) . . . . ?
O14 N7 C4 N7' -49.0(7) . . . . ?
O14 N7 C4 N8' -114.4(6) . . . . ?
O14 N7 C4 C5 47.0(5) . . . . ?
N8 C4 C5 O17 43.87(16) . . . . ?
O15 N8 C4 N6 115.00(19) . . . . ?
O15 N8 C4 N7 0.1(2) . . . . ?
O15 N8 C4 N6' 82.2(4) . . . . ?
O15 N8 C4 N7' -13.4(3) . . . . ?
O15 N8 C4 N8' 128.9(5) . . . . ?
O15 N8 C4 C5 -124.04(19) . . . . ?
O16 N8 C4 N6 -64.7(4) . . . . ?
O16 N8 C4 N7 -179.6(4) . . . . ?
O16 N8 C4 N6' -97.5(6) . . . . ?
O16 N8 C4 N7' 166.9(5) . . . . ?
O16 N8 C4 N8' -50.7(6) . . . . ?
O16 N8 C4 C5 56.3(4) . . . . ?
N6' C4 C5 O17 -154.1(3) . . . . ?
O11' N6' C4 N6 -116.6(7) . . . . ?
O11' N6' C4 N7 32.2(5) . . . . ?
O11' N6' C4 N8 -64.3(8) . . . . ?
O11' N6' C4 N7' 22.3(7) . . . . ?
O11' N6' C4 N8' -93.6(7) . . . . ?
O11' N6' C4 C5 141.8(5) . . . . ?
O12' N6' C4 N6 61.4(15) . . . . ?
O12' N6' C4 N7 -149.8(15) . . . . ?
O12' N6' C4 N8 113.7(15) . . . . ?
O12' N6' C4 N7' -159.7(15) . . . . ?
O12' N6' C4 N8' 84.5(15) . . . . ?
O12' N6' C4 C5 -40.2(15) . . . . ?
N7' C4 C5 O17 -41.7(4) . . . . ?
O13' N7' C4 N6 -88.1(8) . . . . ?
O13' N7' C4 N7 -139.9(10) . . . . ?
O13' N7' C4 N8 15.4(6) . . . . ?
O13' N7' C4 N6' -122.1(7) . . . . ?
O13' N7' C4 N8' -9.5(8) . . . . ?
O13' N7' C4 C5 121.8(6) . . . . ?
O14' N7' C4 N6 101.2(16) . . . . ?
O14' N7' C4 N7 49.5(16) . . . . ?
O14' N7' C4 N8 -155.2(17) . . . . ?
O14' N7' C4 N6' 67.3(17) . . . . ?
O14' N7' C4 N8' 179.9(16) . . . . ?
O14' N7' C4 C5 -48.8(17) . . . . ?
N8' C4 C5 O17 87.0(4) . . . . ?
O15' N8' C4 N6 26.5(7) . . . . ?
O15' N8' C4 N7 -68.3(9) . . . . ?
O15' N8' C4 N8 -139.2(10) . . . . ?
O15' N8' C4 N6' 10.6(9) . . . . ?
O15' N8' C4 N7' -99.5(8) . . . . ?
O15' N8' C4 C5 130.6(7) . . . . ?
O16' N8' C4 N6 -151.6(14) . . . . ?
O16' N8' C4 N7 113.6(13) . . . . ?
O16' N8' C4 N8 42.7(13) . . . . ?
O16' N8' C4 N6' -167.5(13) . . . . ?
O16' N8' C4 N7' 82.4(14) . . . . ?
O16' N8' C4 C5 -47.5(14) . . . . ?
N10 N9 C6 O17 -178.98(13) . . . . ?
N10 N9 C6 O18 0.9(3) . . . . ?
C5 O17 C6 O18 3.8(2) . . . . ?
C5 O17 C6 N9 -176.32(13) . . . . ?
C6 O17 C5 C4 158.89(12) . . . . ?
C6 N9 N10 O19 -0.2(2) . . . . ?
C6 N9 N10 O20 179.96(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_mo_dm15123_0m
_database_code_depnum_ccdc_archive 'CCDC 1469217'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_audit_creation_date             2015-02-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'4-Amino-1,2,4-triazolium 2,2,2-trinitroethyl nitrocarbamate'
_chemical_formula_moiety         'C3 H2 N5 O10, C2 H5 N4'
_chemical_formula_sum            'C5 H7 N9 O10'
_chemical_formula_weight         353.20
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0529(10)
_cell_length_b                   9.9796(17)
_cell_length_c                   11.0845(18)
_cell_angle_alpha                77.305(3)
_cell_angle_beta                 82.986(3)
_cell_angle_gamma                80.736(3)
_cell_volume                     642.06(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0637 before and 0.0319 after correction.
The Ratio of minimum to maximum transmission is 0.8405.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6519
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.583
_diffrn_reflns_theta_min         1.891
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2860
_reflns_number_total             3904
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.1346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1006
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.1035(2) 0.03281(13) 0.14607(11) 0.0329(3) Uani 1 1 d . . . . .
O2 O -0.0439(2) 0.10795(12) 0.30760(11) 0.0320(3) Uani 1 1 d . . . . .
O3 O 0.43367(19) 0.02150(12) 0.31134(11) 0.0299(3) Uani 1 1 d . . . . .
O4 O 0.3072(2) -0.13356(13) 0.46338(10) 0.0352(3) Uani 1 1 d . . . . .
O5 O 0.1516(2) -0.33162(12) 0.34875(11) 0.0346(3) Uani 1 1 d . . . . .
O6 O -0.1485(2) -0.18756(13) 0.37903(12) 0.0360(3) Uani 1 1 d . . . . .
O7 O 0.50290(17) -0.21469(11) 0.18307(9) 0.0219(2) Uani 1 1 d . . . . .
O8 O 0.59262(18) -0.18765(11) -0.02245(9) 0.0257(2) Uani 1 1 d . . . . .
O9 O 0.97187(19) -0.33988(14) -0.06947(10) 0.0324(3) Uani 1 1 d . . . . .
O10 O 1.18821(19) -0.39523(12) 0.07818(11) 0.0309(3) Uani 1 1 d . . . . .
N1 N -0.0097(2) 0.02720(13) 0.23846(12) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.3171(2) -0.06788(13) 0.35759(12) 0.0227(3) Uani 1 1 d . . . . .
N3 N 0.0444(2) -0.21690(13) 0.33911(12) 0.0238(3) Uani 1 1 d . . . . .
N4 N 0.8379(2) -0.31279(13) 0.12678(11) 0.0229(3) Uani 1 1 d . . . . .
N5 N 1.0006(2) -0.34885(13) 0.04031(12) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.1686(2) -0.09905(14) 0.26876(13) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.3015(2) -0.12555(15) 0.15003(13) 0.0204(3) Uani 1 1 d . . . . .
H2A H 0.2134 -0.1700 0.1042 0.024 Uiso 1 1 calc R . . . .
H2B H 0.3374 -0.0371 0.0963 0.024 Uiso 1 1 calc R . . . .
C3 C 0.6463(2) -0.23659(14) 0.08168(13) 0.0193(3) Uani 1 1 d . . . . .
N6 N 0.2493(2) -0.46261(14) -0.35548(12) 0.0240(3) Uani 1 1 d . . . . .
H6A H 0.1316 -0.4008 -0.3642 0.029 Uiso 1 1 d GR . . . .
H6B H 0.2158 -0.5333 -0.2995 0.029 Uiso 1 1 d GR . . . .
N7 N 0.42398(19) -0.40648(12) -0.31956(11) 0.0180(2) Uani 1 1 d . . . . .
N8 N 0.6313(2) -0.32422(13) -0.22309(12) 0.0219(3) Uani 1 1 d . . . . .
N9 N 0.7513(2) -0.33503(13) -0.33341(11) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.4361(2) -0.36608(15) -0.21405(13) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.3245 -0.3676 -0.1458 0.026 Uiso 1 1 calc R . . . .
C5 C 0.6197(2) -0.38563(15) -0.39054(13) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.6555 -0.4054 -0.4712 0.023 Uiso 1 1 calc R . . . .
H8 H 0.685(3) -0.295(2) -0.1688(19) 0.038(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2169(16) . ?
O2 N1 1.2077(17) . ?
O3 N2 1.2123(17) . ?
O4 N2 1.2108(17) . ?
O5 N3 1.2113(17) . ?
O6 N3 1.2103(17) . ?
O7 C2 1.4244(17) . ?
O7 C3 1.3685(17) . ?
O8 C3 1.2120(17) . ?
O9 N5 1.2320(16) . ?
O10 N5 1.2415(16) . ?
N1 C1 1.5261(18) . ?
N2 C1 1.5216(19) . ?
N3 C1 1.5150(19) . ?
N4 N5 1.3512(17) . ?
N4 C3 1.3652(19) . ?
C1 C2 1.508(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N6 H6A 0.8644 . ?
N6 H6B 0.8644 . ?
N6 N7 1.4079(16) . ?
N7 C4 1.3317(18) . ?
N7 C5 1.3586(18) . ?
N8 N9 1.3604(17) . ?
N8 C4 1.3005(19) . ?
N8 H8 0.84(2) . ?
N9 C5 1.2977(18) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?

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
C3 O7 C2 112.54(11) . . ?
O1 N1 C1 114.58(12) . . ?
O2 N1 O1 127.60(13) . . ?
O2 N1 C1 117.81(12) . . ?
O3 N2 C1 114.26(12) . . ?
O4 N2 O3 127.96(13) . . ?
O4 N2 C1 117.78(13) . . ?
O5 N3 C1 115.34(12) . . ?
O6 N3 O5 127.11(14) . . ?
O6 N3 C1 117.55(12) . . ?
N5 N4 C3 115.50(12) . . ?
O9 N5 O10 120.06(12) . . ?
O9 N5 N4 124.31(12) . . ?
O10 N5 N4 115.63(12) . . ?
N2 C1 N1 107.47(11) . . ?
N3 C1 N1 106.33(11) . . ?
N3 C1 N2 107.36(11) . . ?
C2 C1 N1 109.13(11) . . ?
C2 C1 N2 111.69(12) . . ?
C2 C1 N3 114.51(11) . . ?
O7 C2 C1 107.41(11) . . ?
O7 C2 H2A 110.2 . . ?
O7 C2 H2B 110.2 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O8 C3 O7 120.64(13) . . ?
O8 C3 N4 133.12(14) . . ?
N4 C3 O7 106.20(12) . . ?
H6A N6 H6B 109.0 . . ?
N7 N6 H6A 109.7 . . ?
N7 N6 H6B 110.0 . . ?
C4 N7 N6 128.94(12) . . ?
C4 N7 C5 106.83(12) . . ?
C5 N7 N6 124.22(12) . . ?
N9 N8 H8 120.9(14) . . ?
C4 N8 N9 112.22(12) . . ?
C4 N8 H8 126.8(14) . . ?
C5 N9 N8 103.70(12) . . ?
N7 C4 H4 126.9 . . ?
N8 C4 N7 106.30(13) . . ?
N8 C4 H4 126.9 . . ?
N7 C5 H5 124.5 . . ?
N9 C5 N7 110.95(13) . . ?
N9 C5 H5 124.5 . . ?

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
N8 H8 O8 0.84(2) 2.11(2) 2.8215(16) 142.3(18) .
N8 H8 O9 0.84(2) 2.10(2) 2.7948(17) 139.0(18) .

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 N1 C1 N2 162.18(12) . . . . ?
O1 N1 C1 N3 -83.11(14) . . . . ?
O1 N1 C1 C2 40.89(16) . . . . ?
O2 N1 C1 N2 -18.70(17) . . . . ?
O2 N1 C1 N3 96.01(14) . . . . ?
O2 N1 C1 C2 -139.99(13) . . . . ?
O3 N2 C1 N1 -68.79(15) . . . . ?
O3 N2 C1 N3 177.18(11) . . . . ?
O3 N2 C1 C2 50.87(16) . . . . ?
O4 N2 C1 N1 111.58(14) . . . . ?
O4 N2 C1 N3 -2.45(17) . . . . ?
O4 N2 C1 C2 -128.75(14) . . . . ?
O5 N3 C1 N1 165.50(12) . . . . ?
O5 N3 C1 N2 -79.71(15) . . . . ?
O5 N3 C1 C2 44.91(17) . . . . ?
O6 N3 C1 N1 -14.34(17) . . . . ?
O6 N3 C1 N2 100.45(15) . . . . ?
O6 N3 C1 C2 -134.93(14) . . . . ?
N1 C1 C2 O7 163.15(11) . . . . ?
N2 C1 C2 O7 44.47(15) . . . . ?
N3 C1 C2 O7 -77.83(14) . . . . ?
N5 N4 C3 O7 178.36(11) . . . . ?
N5 N4 C3 O8 -3.9(2) . . . . ?
C2 O7 C3 O8 -3.21(18) . . . . ?
C2 O7 C3 N4 174.85(11) . . . . ?
C3 O7 C2 C1 -174.83(11) . . . . ?
C3 N4 N5 O9 -13.7(2) . . . . ?
C3 N4 N5 O10 167.26(12) . . . . ?
N6 N7 C4 N8 178.76(13) . . . . ?
N6 N7 C5 N9 -178.86(13) . . . . ?
N8 N9 C5 N7 -0.11(16) . . . . ?
N9 N8 C4 N7 0.27(17) . . . . ?
C4 N7 C5 N9 0.27(16) . . . . ?
C4 N8 N9 C5 -0.10(17) . . . . ?
C5 N7 C4 N8 -0.32(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dm15250
_database_code_depnum_ccdc_archive 'CCDC 1469218'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
'3-Amino-1,2,4-triazolium 2,2,2-trinitroethyl nitrocarbamate'
_chemical_formula_moiety         'C3 H2 N5 O10, C2 H5 N4'
_chemical_formula_sum            'C5 H7 N9 O10'
_chemical_formula_weight         353.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   29.106(4)
_cell_length_b                   7.0395(9)
_cell_length_c                   6.4650(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1324.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3452
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.405
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0678 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.8996.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12833
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_min         1.399
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                3370
_reflns_number_total             3845
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N9(H9), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.02072(6) -0.5468(2) -0.3555(4) 0.0367(4) Uani 1 1 d . . . . .
O2 O 0.01717(6) -0.2851(3) -0.3174(3) 0.0367(5) Uani 1 1 d . . . . .
O3 O -0.06522(7) 0.0491(2) -0.2847(4) 0.0411(5) Uani 1 1 d . . . . .
O4 O -0.03398(7) -0.0864(3) -0.0185(3) 0.0367(4) Uani 1 1 d . . . . .
O5 O -0.12754(5) -0.2410(2) -0.4755(3) 0.0260(3) Uani 1 1 d . . . . .
O6 O -0.06101(7) -0.2407(3) -0.6277(3) 0.0413(5) Uani 1 1 d . . . . .
O7 O -0.12541(5) -0.2808(2) -0.0369(3) 0.0196(3) Uani 1 1 d . . . . .
O8 O -0.17855(5) -0.4950(2) -0.1413(3) 0.0237(3) Uani 1 1 d . . . . .
O9 O -0.26081(5) -0.36952(19) -0.0617(3) 0.0222(3) Uani 1 1 d . . . . .
O10 O -0.26562(5) -0.0947(2) 0.0824(3) 0.0217(3) Uani 1 1 d . . . . .
N1 N -0.01736(6) -0.3786(3) -0.3176(3) 0.0225(4) Uani 1 1 d . . . . .
N2 N -0.05267(7) -0.0860(3) -0.1853(3) 0.0244(4) Uani 1 1 d . . . . .
N3 N -0.08597(6) -0.2541(2) -0.4785(3) 0.0213(4) Uani 1 1 d . . . . .
N4 N -0.19650(6) -0.2021(2) 0.0193(3) 0.0174(3) Uani 1 1 d . . . . .
N5 N -0.24216(6) -0.2263(2) 0.0115(3) 0.0160(3) Uani 1 1 d . . . . .
C1 C -0.06280(6) -0.2831(3) -0.2714(3) 0.0169(4) Uani 1 1 d . . . . .
C2 C -0.09045(7) -0.3991(3) -0.1180(4) 0.0194(4) Uani 1 1 d . . . . .
H2A H -0.1042 -0.5106 -0.1877 0.023 Uiso 1 1 calc R . . . .
H2B H -0.0703 -0.4450 -0.0050 0.023 Uiso 1 1 calc R . . . .
C3 C -0.17011(6) -0.3438(3) -0.0630(3) 0.0166(4) Uani 1 1 d . . . . .
N6 N -0.26009(6) -0.7386(2) -0.2340(3) 0.0188(4) Uani 1 1 d . . . . .
H6A H -0.2439 -0.6425 -0.1867 0.023 Uiso 1 1 calc R . . . .
H6B H -0.2462 -0.8354 -0.2931 0.023 Uiso 1 1 calc R . . . .
N7 N -0.33160(6) -0.6034(2) -0.1323(3) 0.0233(4) Uani 1 1 d . . . . .
H7 H -0.3210 -0.4978 -0.0774 0.028 Uiso 1 1 calc R . . . .
N8 N -0.37766(6) -0.6499(3) -0.1411(4) 0.0325(5) Uani 1 1 d . . . . .
N9 N -0.33422(6) -0.8736(2) -0.2812(3) 0.0202(4) Uani 1 1 d . . . . .
H9 H -0.3268 -0.9806 -0.3432 0.024 Uiso 1 1 calc R . . . .
C4 C -0.30511(7) -0.7374(3) -0.2166(3) 0.0169(4) Uani 1 1 d . . . . .
C5 C -0.37768(8) -0.8139(3) -0.2322(4) 0.0275(5) Uani 1 1 d . . . . .
H5 H -0.4047 -0.8846 -0.2616 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.213(2) . ?
O2 N1 1.202(2) . ?
O3 N2 1.205(3) . ?
O4 N2 1.208(3) . ?
O5 N3 1.213(2) . ?
O6 N3 1.211(3) . ?
O7 C2 1.415(2) . ?
O7 C3 1.385(2) . ?
O8 C3 1.204(2) . ?
O9 N5 1.239(2) . ?
O10 N5 1.239(2) . ?
N1 C1 1.514(3) . ?
N2 C1 1.523(3) . ?
N3 C1 1.513(3) . ?
N4 N5 1.341(2) . ?
N4 C3 1.367(3) . ?
C1 C2 1.516(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C4 1.315(3) . ?
N7 H7 0.8800 . ?
N7 N8 1.381(2) . ?
N7 C4 1.335(3) . ?
N8 C5 1.296(3) . ?
N9 H9 0.8800 . ?
N9 C4 1.346(3) . ?
N9 C5 1.370(3) . ?
C5 H5 0.9500 . ?

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
C3 O7 C2 116.26(16) . . ?
O1 N1 C1 113.79(17) . . ?
O2 N1 O1 127.1(2) . . ?
O2 N1 C1 119.13(19) . . ?
O3 N2 O4 127.9(2) . . ?
O3 N2 C1 117.75(19) . . ?
O4 N2 C1 114.26(19) . . ?
O5 N3 C1 116.11(18) . . ?
O6 N3 O5 127.2(2) . . ?
O6 N3 C1 116.60(17) . . ?
N5 N4 C3 116.71(16) . . ?
O9 N5 O10 120.55(16) . . ?
O9 N5 N4 123.52(15) . . ?
O10 N5 N4 115.93(15) . . ?
N1 C1 N2 107.92(16) . . ?
N1 C1 C2 110.70(16) . . ?
N3 C1 N1 105.92(17) . . ?
N3 C1 N2 106.66(16) . . ?
N3 C1 C2 114.52(16) . . ?
C2 C1 N2 110.77(18) . . ?
O7 C2 C1 107.87(16) . . ?
O7 C2 H2A 110.1 . . ?
O7 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O8 C3 O7 121.71(17) . . ?
O8 C3 N4 133.98(18) . . ?
N4 C3 O7 104.31(16) . . ?
H6A N6 H6B 120.0 . . ?
C4 N6 H6A 120.0 . . ?
C4 N6 H6B 120.0 . . ?
N8 N7 H7 124.0 . . ?
C4 N7 H7 124.0 . . ?
C4 N7 N8 112.10(17) . . ?
C5 N8 N7 103.31(18) . . ?
C4 N9 H9 126.5 . . ?
C4 N9 C5 106.90(18) . . ?
C5 N9 H9 126.5 . . ?
N6 C4 N7 127.94(18) . . ?
N6 C4 N9 126.59(18) . . ?
N7 C4 N9 105.47(18) . . ?
N8 C5 N9 112.22(19) . . ?
N8 C5 H5 123.9 . . ?
N9 C5 H5 123.9 . . ?

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 H6A O9 0.88 2.14 2.827(2) 134.2 .
N6 H6B O10 0.88 2.02 2.873(2) 161.7 3_444
N7 H7 O9 0.88 1.97 2.676(2) 136.0 .
N9 H9 N4 0.88 1.92 2.795(2) 173.4 3_444

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 N1 C1 N2 168.8(2) . . . . ?
O1 N1 C1 N3 -77.3(2) . . . . ?
O1 N1 C1 C2 47.4(3) . . . . ?
O2 N1 C1 N2 -12.5(3) . . . . ?
O2 N1 C1 N3 101.4(2) . . . . ?
O2 N1 C1 C2 -133.9(2) . . . . ?
O3 N2 C1 N1 115.9(2) . . . . ?
O3 N2 C1 N3 2.4(3) . . . . ?
O3 N2 C1 C2 -122.8(2) . . . . ?
O4 N2 C1 N1 -66.6(2) . . . . ?
O4 N2 C1 N3 179.96(18) . . . . ?
O4 N2 C1 C2 54.7(2) . . . . ?
O5 N3 C1 N1 155.73(16) . . . . ?
O5 N3 C1 N2 -89.5(2) . . . . ?
O5 N3 C1 C2 33.4(2) . . . . ?
O6 N3 C1 N1 -26.5(2) . . . . ?
O6 N3 C1 N2 88.3(2) . . . . ?
O6 N3 C1 C2 -148.8(2) . . . . ?
N1 C1 C2 O7 163.66(17) . . . . ?
N2 C1 C2 O7 44.0(2) . . . . ?
N3 C1 C2 O7 -76.7(2) . . . . ?
N5 N4 C3 O7 179.18(16) . . . . ?
N5 N4 C3 O8 -1.8(4) . . . . ?
C2 O7 C3 O8 3.4(3) . . . . ?
C2 O7 C3 N4 -177.38(18) . . . . ?
C3 O7 C2 C1 122.29(19) . . . . ?
C3 N4 N5 O9 1.3(3) . . . . ?
C3 N4 N5 O10 -178.40(19) . . . . ?
N7 N8 C5 N9 0.0(3) . . . . ?
N8 N7 C4 N6 179.9(2) . . . . ?
N8 N7 C4 N9 -0.1(3) . . . . ?
C4 N7 N8 C5 0.0(3) . . . . ?
C4 N9 C5 N8 -0.1(3) . . . . ?
C5 N9 C4 N6 -179.9(2) . . . . ?
C5 N9 C4 N7 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dm15270
_database_code_depnum_ccdc_archive 'CCDC 1469219'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_audit_creation_date             2015-04-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        'Ammonium 2,2,2-trinitroethyl nitrocarbamate'
_chemical_formula_moiety         '2(C3 H2 N5 O10), 2(H4 N), 2(H2 O)'
_chemical_formula_sum            'C6 H16 N12 O22'
_chemical_formula_weight         608.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.7423(16)
_cell_length_b                   6.4498(7)
_cell_length_c                   12.4148(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.507(2)
_cell_angle_gamma                90
_cell_volume                     1152.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4037
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.444
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0565 before and 0.0350 after correction.
The Ratio of minimum to maximum transmission is 0.9205.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11122
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.609
_diffrn_reflns_theta_min         2.831
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2913
_reflns_number_total             3508
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.3751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0954
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All N(H,H) groups
2. Restrained distances
 N1-H1A
 0.82 with sigma of 0.01
 N1-H1B
 0.82 with sigma of 0.01
 H1A-H1B
 1.296731 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.01905(6) 0.68170(13) 0.08827(6) 0.02022(17) Uani 1 1 d . . . . .
O2 O -0.01823(6) 0.81453(13) -0.07491(7) 0.02258(18) Uani 1 1 d . . . . .
O3 O 0.20003(6) 0.66396(13) 0.16830(6) 0.02081(17) Uani 1 1 d . . . . .
O4 O 0.26999(5) 0.61536(13) 0.02485(6) 0.01997(17) Uani 1 1 d . . . . .
O5 O 0.22810(8) 0.22084(18) 0.10978(14) 0.0575(4) Uani 1 1 d . . . . .
O6 O 0.34084(8) 0.00288(17) 0.14366(12) 0.0525(3) Uani 1 1 d . . . . .
O7 O 0.48908(7) 0.31606(15) 0.22610(8) 0.0329(2) Uani 1 1 d . . . . .
O8 O 0.51349(8) 0.16603(19) 0.07824(11) 0.0482(3) Uani 1 1 d . . . . .
O9 O 0.30570(9) 0.1577(2) -0.09311(10) 0.0486(3) Uani 1 1 d . . . . .
O10 O 0.40450(8) 0.4069(2) -0.09288(9) 0.0429(3) Uani 1 1 d . . . . .
N2 N 0.03972(6) 0.74144(14) 0.00247(7) 0.01572(17) Uani 1 1 d . . . . .
N3 N 0.12704(6) 0.72357(14) -0.01754(7) 0.01690(18) Uani 1 1 d . . . . .
N4 N 0.30631(8) 0.16813(17) 0.11296(10) 0.0308(2) Uani 1 1 d . . . . .
N5 N 0.46731(7) 0.26232(17) 0.13060(10) 0.0282(2) Uani 1 1 d . . . . .
N6 N 0.35852(8) 0.29160(19) -0.04938(9) 0.0308(2) Uani 1 1 d . . . . .
C1 C 0.36907(8) 0.32429(18) 0.07399(10) 0.0220(2) Uani 1 1 d . . . . .
C2 C 0.35077(7) 0.54863(17) 0.10013(9) 0.0200(2) Uani 1 1 d . . . . .
H2A H 0.3418 0.5601 0.1766 0.024 Uiso 1 1 calc R . . . .
H2B H 0.4044 0.6362 0.0932 0.024 Uiso 1 1 calc R . . . .
C3 C 0.19489(7) 0.66723(16) 0.06983(8) 0.01582(19) Uani 1 1 d . . . . .
N1 N 0.08756(7) 0.42980(16) 0.28943(8) 0.01918(19) Uani 1 1 d D . . . .
H1A H 0.1112(10) 0.491(2) 0.2435(11) 0.029 Uiso 1 1 d DR . . . .
H1B H 0.0295(6) 0.445(2) 0.2695(12) 0.029 Uiso 1 1 d DR . . . .
H1C H 0.1026(11) 0.293(3) 0.2865(13) 0.030(4) Uiso 1 1 d . . . . .
H1D H 0.1081(12) 0.486(3) 0.3543(14) 0.031(4) Uiso 1 1 d . . . . .
O1S O 0.11410(6) 0.50775(14) -0.21634(7) 0.02165(18) Uani 1 1 d . . . . .
H1SA H 0.1218(13) 0.573(3) -0.1585(17) 0.043(5) Uiso 1 1 d . . . . .
H1SB H 0.1394(12) 0.574(3) -0.2557(15) 0.035(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2316(12) . ?
O2 N2 1.2327(12) . ?
O3 C3 1.2086(13) . ?
O4 C2 1.4124(13) . ?
O4 C3 1.3847(13) . ?
O5 N4 1.1944(16) . ?
O6 N4 1.2068(16) . ?
O7 N5 1.2101(15) . ?
O8 N5 1.2097(15) . ?
O9 N6 1.2098(16) . ?
O10 N6 1.2096(17) . ?
N2 N3 1.3676(13) . ?
N3 C3 1.3562(13) . ?
N4 C1 1.5160(16) . ?
N5 C1 1.5200(16) . ?
N6 C1 1.5203(17) . ?
C1 C2 1.5198(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N1 H1A 0.831(9) . ?
N1 H1B 0.843(9) . ?
N1 H1C 0.910(17) . ?
N1 H1D 0.876(17) . ?
O1S H1SA 0.82(2) . ?
O1S H1SB 0.799(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O4 C2 116.10(8) . . ?
O1 N2 O2 122.29(9) . . ?
O1 N2 N3 123.35(9) . . ?
O2 N2 N3 114.29(8) . . ?
C3 N3 N2 115.94(8) . . ?
O5 N4 O6 126.87(13) . . ?
O5 N4 C1 116.86(11) . . ?
O6 N4 C1 116.27(11) . . ?
O7 N5 C1 113.68(10) . . ?
O8 N5 O7 127.80(12) . . ?
O8 N5 C1 118.51(11) . . ?
O9 N6 C1 117.81(12) . . ?
O10 N6 O9 127.37(13) . . ?
O10 N6 C1 114.81(11) . . ?
N4 C1 N5 105.31(10) . . ?
N4 C1 N6 107.04(10) . . ?
N4 C1 C2 114.55(10) . . ?
N5 C1 N6 107.98(10) . . ?
C2 C1 N5 110.31(9) . . ?
C2 C1 N6 111.28(10) . . ?
O4 C2 C1 108.18(9) . . ?
O4 C2 H2A 110.1 . . ?
O4 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
O3 C3 O4 121.55(10) . . ?
O3 C3 N3 133.44(10) . . ?
N3 C3 O4 104.94(8) . . ?
H1A N1 H1B 107.1(13) . . ?
H1A N1 H1C 106.9(15) . . ?
H1A N1 H1D 108.6(16) . . ?
H1B N1 H1C 110.0(15) . . ?
H1B N1 H1D 110.3(15) . . ?
H1C N1 H1D 113.7(15) . . ?
H1SA O1S H1SB 105.6(18) . . ?

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
N1 H1A O3 0.831(9) 2.087(9) 2.8934(13) 163.5(15) .
N1 H1C O1S 0.910(17) 1.950(18) 2.8521(14) 170.5(15) 4_566
O1S H1SA N3 0.82(2) 1.99(2) 2.8038(12) 174.1(19) .

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 N2 N3 C3 -10.62(14) . . . . ?
O2 N2 N3 C3 172.43(9) . . . . ?
O5 N4 C1 N5 156.17(13) . . . . ?
O5 N4 C1 N6 -89.08(15) . . . . ?
O5 N4 C1 C2 34.79(17) . . . . ?
O6 N4 C1 N5 -24.06(15) . . . . ?
O6 N4 C1 N6 90.68(14) . . . . ?
O6 N4 C1 C2 -145.44(12) . . . . ?
O7 N5 C1 N4 -78.39(12) . . . . ?
O7 N5 C1 N6 167.51(10) . . . . ?
O7 N5 C1 C2 45.71(14) . . . . ?
O8 N5 C1 N4 100.73(14) . . . . ?
O8 N5 C1 N6 -13.37(16) . . . . ?
O8 N5 C1 C2 -135.17(12) . . . . ?
O9 N6 C1 N4 0.30(15) . . . . ?
O9 N6 C1 N5 113.24(13) . . . . ?
O9 N6 C1 C2 -125.56(12) . . . . ?
O10 N6 C1 N4 179.63(11) . . . . ?
O10 N6 C1 N5 -67.43(14) . . . . ?
O10 N6 C1 C2 53.76(14) . . . . ?
N2 N3 C3 O3 -15.97(17) . . . . ?
N2 N3 C3 O4 167.14(8) . . . . ?
N4 C1 C2 O4 -76.52(12) . . . . ?
N5 C1 C2 O4 164.89(9) . . . . ?
N6 C1 C2 O4 45.06(12) . . . . ?
C2 O4 C3 O3 3.15(15) . . . . ?
C2 O4 C3 N3 -179.50(9) . . . . ?
C3 O4 C2 C1 115.94(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
