# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_shrv250

_audit_creation_date             2013-09-23
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 (E)-2,2,2-trinitro-N-(2,2,2-trinitroethylidene)ethanamine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 N7 O12'
_chemical_formula_sum            'C4 H3 N7 O12'
_chemical_formula_weight         341.13

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   12.523(2)
_cell_length_b                   11.3630(19)
_cell_length_c                   16.558(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2356.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9583
_exptl_absorpt_correction_T_max  0.9961

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19773
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         26.44
_reflns_number_total             2409
_reflns_number_gt                1793
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.4336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2409
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.91810(13) 0.57450(13) 0.72239(10) 0.0174(4) Uani 1 1 d . . .
C2 C 0.88391(15) 0.68786(14) 0.68104(10) 0.0215(4) Uani 1 1 d . . .
H2A H 0.8444 0.7391 0.7191 0.026 Uiso 1 1 calc R . .
H2B H 0.9469 0.7314 0.6607 0.026 Uiso 1 1 calc R . .
N3 N 0.81522(11) 0.65160(12) 0.61434(8) 0.0214(3) Uani 1 1 d . . .
C4 C 0.78306(13) 0.72683(14) 0.56506(10) 0.0195(4) Uani 1 1 d . . .
H4 H 0.8035 0.8071 0.5694 0.023 Uiso 1 1 calc R . .
C5 C 0.71035(13) 0.68517(13) 0.49823(10) 0.0173(4) Uani 1 1 d . . .
N6 N 1.00107(12) 0.50474(12) 0.67488(9) 0.0237(3) Uani 1 1 d . . .
O7 O 1.01925(11) 0.53760(12) 0.60679(8) 0.0361(3) Uani 1 1 d . . .
O8 O 1.04147(11) 0.42243(11) 0.71072(9) 0.0351(3) Uani 1 1 d . . .
N9 N 0.82044(11) 0.49706(12) 0.73446(8) 0.0209(3) Uani 1 1 d . . .
O10 O 0.74976(11) 0.54295(11) 0.77353(8) 0.0332(3) Uani 1 1 d . . .
O11 O 0.81870(11) 0.40107(10) 0.70234(8) 0.0300(3) Uani 1 1 d . . .
N12 N 0.96992(11) 0.59600(12) 0.80359(8) 0.0209(3) Uani 1 1 d . . .
O13 O 1.03823(10) 0.67285(10) 0.80293(8) 0.0290(3) Uani 1 1 d . . .
O14 O 0.94327(11) 0.53543(12) 0.86019(8) 0.0333(3) Uani 1 1 d . . .
N15 N 0.70245(11) 0.55151(11) 0.49856(8) 0.0194(3) Uani 1 1 d . . .
O16 O 0.64589(10) 0.51040(10) 0.55076(8) 0.0291(3) Uani 1 1 d . . .
O17 O 0.75701(10) 0.49912(10) 0.45003(7) 0.0280(3) Uani 1 1 d . . .
N18 N 0.59815(11) 0.73572(12) 0.50501(8) 0.0212(3) Uani 1 1 d . . .
O19 O 0.59232(11) 0.82788(10) 0.54152(8) 0.0308(3) Uani 1 1 d . . .
O20 O 0.52659(10) 0.68227(12) 0.47202(8) 0.0344(3) Uani 1 1 d . . .
N21 N 0.75287(13) 0.72211(12) 0.41536(8) 0.0234(3) Uani 1 1 d . . .
O22 O 0.84796(11) 0.74161(12) 0.41321(8) 0.0345(3) Uani 1 1 d . . .
O23 O 0.68977(12) 0.72731(13) 0.36005(8) 0.0384(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N12 1.513(2) . ?
C1 N9 1.520(2) . ?
C1 C2 1.520(2) . ?
C1 N6 1.525(2) . ?
C2 N3 1.459(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 C4 1.248(2) . ?
C4 C5 1.509(2) . ?
C4 H4 0.9500 . ?
C5 N15 1.522(2) . ?
C5 N18 1.522(2) . ?
C5 N21 1.531(2) . ?
N6 O7 1.2094(19) . ?
N6 O8 1.2176(19) . ?
N9 O11 1.2137(18) . ?
N9 O10 1.2140(18) . ?
N12 O14 1.2098(18) . ?
N12 O13 1.2224(18) . ?
N15 O16 1.2112(18) . ?
N15 O17 1.2112(18) . ?
N18 O19 1.2114(18) . ?
N18 O20 1.2126(18) . ?
N21 O23 1.211(2) . ?
N21 O22 1.212(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
N12 C1 N9 108.77(12) . . ?
N12 C1 C2 112.60(12) . . ?
N9 C1 C2 108.85(13) . . ?
N12 C1 N6 104.48(12) . . ?
N9 C1 N6 108.36(12) . . ?
C2 C1 N6 113.58(13) . . ?
N3 C2 C1 105.53(12) . . ?
N3 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
N3 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
C4 N3 C2 119.44(14) . . ?
N3 C4 C5 117.33(15) . . ?
N3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C4 C5 N15 110.46(13) . . ?
C4 C5 N18 112.61(13) . . ?
N15 C5 N18 108.44(13) . . ?
C4 C5 N21 111.18(13) . . ?
N15 C5 N21 107.43(12) . . ?
N18 C5 N21 106.49(12) . . ?
O7 N6 O8 127.83(15) . . ?
O7 N6 C1 116.65(14) . . ?
O8 N6 C1 115.53(14) . . ?
O11 N9 O10 127.33(14) . . ?
O11 N9 C1 118.50(13) . . ?
O10 N9 C1 114.09(13) . . ?
O14 N12 O13 127.33(14) . . ?
O14 N12 C1 118.57(13) . . ?
O13 N12 C1 114.05(13) . . ?
O16 N15 O17 127.86(14) . . ?
O16 N15 C5 115.18(13) . . ?
O17 N15 C5 116.84(13) . . ?
O19 N18 O20 127.82(15) . . ?
O19 N18 C5 114.76(14) . . ?
O20 N18 C5 117.38(13) . . ?
O23 N21 O22 127.60(15) . . ?
O23 N21 C5 117.66(15) . . ?
O22 N21 C5 114.74(14) . . ?

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
N12 C1 C2 N3 -167.44(13) . . . . ?
N9 C1 C2 N3 -46.75(16) . . . . ?
N6 C1 C2 N3 74.06(17) . . . . ?
C1 C2 N3 C4 -173.52(15) . . . . ?
C2 N3 C4 C5 -178.74(14) . . . . ?
N3 C4 C5 N15 -7.6(2) . . . . ?
N3 C4 C5 N18 113.84(17) . . . . ?
N3 C4 C5 N21 -126.75(16) . . . . ?
N12 C1 N6 O7 -132.61(14) . . . . ?
N9 C1 N6 O7 111.55(16) . . . . ?
C2 C1 N6 O7 -9.5(2) . . . . ?
N12 C1 N6 O8 47.08(17) . . . . ?
N9 C1 N6 O8 -68.76(17) . . . . ?
C2 C1 N6 O8 170.15(14) . . . . ?
N12 C1 N9 O11 -117.85(15) . . . . ?
C2 C1 N9 O11 119.13(15) . . . . ?
N6 C1 N9 O11 -4.84(19) . . . . ?
N12 C1 N9 O10 65.28(17) . . . . ?
C2 C1 N9 O10 -57.74(17) . . . . ?
N6 C1 N9 O10 178.30(13) . . . . ?
N9 C1 N12 O14 13.88(19) . . . . ?
C2 C1 N12 O14 134.61(16) . . . . ?
N6 C1 N12 O14 -101.68(16) . . . . ?
N9 C1 N12 O13 -168.31(13) . . . . ?
C2 C1 N12 O13 -47.57(19) . . . . ?
N6 C1 N12 O13 76.13(15) . . . . ?
C4 C5 N15 O16 76.49(17) . . . . ?
N18 C5 N15 O16 -47.36(17) . . . . ?
N21 C5 N15 O16 -162.08(14) . . . . ?
C4 C5 N15 O17 -99.81(16) . . . . ?
N18 C5 N15 O17 136.34(14) . . . . ?
N21 C5 N15 O17 21.62(19) . . . . ?
C4 C5 N18 O19 24.68(19) . . . . ?
N15 C5 N18 O19 147.24(13) . . . . ?
N21 C5 N18 O19 -97.42(15) . . . . ?
C4 C5 N18 O20 -157.35(14) . . . . ?
N15 C5 N18 O20 -34.80(19) . . . . ?
N21 C5 N18 O20 80.54(16) . . . . ?
C4 C5 N21 O23 -157.88(14) . . . . ?
N15 C5 N21 O23 81.14(17) . . . . ?
N18 C5 N21 O23 -34.88(18) . . . . ?
C4 C5 N21 O22 22.94(18) . . . . ?
N15 C5 N21 O22 -98.03(15) . . . . ?
N18 C5 N21 O22 145.94(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 969795'
