2,4,6-Tri­nitro-2,4,6,8-tetra­aza­bi­cyclo­[3.3.0]octan-7-one

Butcher, R.J.; Evans, R.; Gilardi, R.

doi:10.1107/S160053680401880X

2,4,6-Trinitro-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one

The structure of 2,4,6-trinitro-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one, C₄H₅N₇O₇, is reported. The molecule contains two unsymmetrically substituted planar fused five-membered rings with a cis junction between them.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401880X/fl6113sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680401880X/fl6113Isup2.hkl Contains datablock I

CCDC reference: 251725

checkCIF report

Key indicators

Single-crystal X-ray study
T = 94 K
Mean (C-C) = 0.002 Å
R factor = 0.035
wR factor = 0.087
Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O4A    ..  N4A     ..       2.81 Ang.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT430_ALERT_2_C Short Inter D...A Contact  O2A    ..  O4B     ..       2.89 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,4,8-trinitro-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one top

Crystal data top

C₄H₅N₇O₇	F(000) = 536
M_r = 263.15	D_x = 1.959 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3962 (12) Å	Cell parameters from 4730 reflections
b = 6.4089 (7) Å	θ = 2.6–26.4°
c = 12.3267 (13) Å	µ = 0.19 mm⁻¹
β = 97.786 (2)°	T = 94 K
V = 892.01 (16) Å³	Faceted brick, colorless
Z = 4	0.38 × 0.28 × 0.26 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1816 independent reflections
Radiation source: fine-focus sealed tube	1662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: integration (Wuensch & Prewitt, 1965)	h = −14→14
T_min = 0.935, T_max = 0.957	k = −8→7
5880 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0408P)² + 0.4733P] where P = (F_o² + 2F_c²)/3
1816 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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

Refinement. 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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.23819 (13)	0.3106 (2)	0.25848 (11)	0.0142 (3)
H1	0.1811	0.2063	0.2814	0.017*
N2	0.19933 (12)	0.3969 (2)	0.14998 (10)	0.0190 (3)
N2A	0.17937 (10)	0.2712 (2)	0.06298 (10)	0.0155 (3)
O2A	0.14250 (10)	0.35235 (18)	−0.02520 (8)	0.0218 (3)
O2B	0.20144 (10)	0.08454 (17)	0.07874 (9)	0.0202 (3)
C3	0.17288 (14)	0.6193 (2)	0.14282 (12)	0.0172 (3)
H3A	0.0917	0.6460	0.1058	0.021*
H3B	0.2305	0.6960	0.1045	0.021*
N4	0.18504 (10)	0.6734 (2)	0.25966 (10)	0.0145 (3)
N4A	0.08590 (11)	0.7637 (2)	0.29647 (10)	0.0148 (3)
O4A	0.02421 (9)	0.87154 (17)	0.22884 (9)	0.0203 (3)
O4B	0.07162 (9)	0.73897 (18)	0.39110 (9)	0.0192 (3)
C5	0.24503 (12)	0.5110 (2)	0.32855 (11)	0.0140 (3)
H5	0.2108	0.4918	0.3984	0.017*
N6	0.37274 (10)	0.5452 (2)	0.34674 (10)	0.0155 (3)
N6A	0.41858 (11)	0.7013 (2)	0.41883 (10)	0.0164 (3)
O6A	0.52556 (9)	0.71164 (18)	0.44186 (9)	0.0216 (3)
O6B	0.34467 (10)	0.81506 (18)	0.45017 (9)	0.0216 (3)
C7	0.43940 (13)	0.3747 (2)	0.31217 (11)	0.0152 (3)
O7	0.54561 (9)	0.36373 (17)	0.31827 (9)	0.0182 (3)
N8	0.35740 (11)	0.2336 (2)	0.27083 (11)	0.0163 (3)
H8	0.3753 (17)	0.129 (3)	0.2314 (15)	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0149 (7)	0.0139 (7)	0.0136 (7)	−0.0003 (5)	0.0010 (5)	0.0004 (6)
N2	0.0279 (7)	0.0136 (7)	0.0139 (6)	0.0028 (5)	−0.0027 (5)	−0.0012 (5)
N2A	0.0145 (6)	0.0159 (7)	0.0160 (6)	−0.0005 (5)	0.0017 (5)	−0.0020 (5)
O2A	0.0293 (6)	0.0228 (6)	0.0124 (5)	0.0029 (5)	0.0001 (4)	0.0008 (4)
O2B	0.0255 (6)	0.0143 (6)	0.0206 (5)	0.0012 (4)	0.0018 (4)	−0.0021 (4)
C3	0.0237 (7)	0.0137 (7)	0.0145 (7)	0.0028 (6)	0.0044 (6)	−0.0001 (6)
N4	0.0143 (6)	0.0157 (7)	0.0137 (6)	0.0025 (5)	0.0027 (4)	0.0010 (5)
N4A	0.0141 (6)	0.0123 (6)	0.0179 (6)	−0.0015 (5)	0.0013 (5)	−0.0022 (5)
O4A	0.0182 (5)	0.0178 (6)	0.0243 (6)	0.0049 (4)	0.0009 (4)	0.0033 (5)
O4B	0.0193 (5)	0.0219 (6)	0.0171 (6)	0.0005 (4)	0.0044 (4)	−0.0037 (4)
C5	0.0143 (7)	0.0134 (7)	0.0143 (7)	0.0003 (5)	0.0016 (5)	0.0012 (5)
N6	0.0142 (6)	0.0154 (6)	0.0162 (6)	0.0001 (5)	−0.0002 (4)	−0.0027 (5)
N6A	0.0185 (6)	0.0166 (7)	0.0139 (6)	−0.0029 (5)	0.0011 (5)	−0.0002 (5)
O6A	0.0167 (5)	0.0254 (6)	0.0218 (6)	−0.0049 (5)	−0.0003 (4)	−0.0033 (5)
O6B	0.0218 (6)	0.0205 (6)	0.0230 (6)	0.0007 (5)	0.0041 (4)	−0.0070 (5)
C7	0.0176 (7)	0.0150 (7)	0.0130 (7)	0.0011 (6)	0.0015 (5)	0.0027 (5)
O7	0.0138 (5)	0.0186 (6)	0.0222 (6)	0.0009 (4)	0.0021 (4)	0.0008 (4)
N8	0.0147 (6)	0.0147 (7)	0.0194 (6)	0.0017 (5)	0.0020 (5)	−0.0027 (5)

Geometric parameters (Å, º) top

C1—N8	1.4339 (19)	N4—C5	1.4539 (18)
C1—N2	1.4596 (19)	N4A—O4B	1.2098 (17)
C1—C5	1.544 (2)	N4A—O4A	1.2281 (16)
C1—H1	1.0000	O4A—N4Aⁱⁱ	2.8075 (17)
N2—N2A	1.3358 (18)	C5—N6	1.4588 (18)
N2—C3	1.457 (2)	C5—H5	1.0000
N2A—O2A	1.2268 (17)	N6—N6A	1.3922 (17)
N2A—O2B	1.2324 (18)	N6—C7	1.4285 (19)
O2A—O4Bⁱ	2.8898 (16)	N6A—O6A	1.2155 (16)
C3—N4	1.4695 (18)	N6A—O6B	1.2158 (17)
C3—H3A	0.9900	C7—O7	1.2046 (18)
C3—H3B	0.9900	C7—N8	1.350 (2)
N4—N4A	1.3987 (17)	N8—H8	0.87 (2)

N8—C1—N2	113.15 (12)	O4B—N4A—O4A	126.07 (13)
N8—C1—C5	104.57 (11)	O4B—N4A—N4	118.60 (12)
N2—C1—C5	100.57 (11)	O4A—N4A—N4	115.21 (12)
N8—C1—H1	112.6	N4—C5—N6	111.27 (12)
N2—C1—H1	112.6	N4—C5—C1	106.54 (11)
C5—C1—H1	112.6	N6—C5—C1	100.64 (11)
N2A—N2—C3	122.00 (12)	N4—C5—H5	112.6
N2A—N2—C1	120.31 (12)	N6—C5—H5	112.6
C3—N2—C1	117.44 (12)	C1—C5—H5	112.6
O2A—N2A—O2B	126.11 (13)	N6A—N6—C7	124.85 (12)
O2A—N2A—N2	117.15 (13)	N6A—N6—C5	119.10 (12)
O2B—N2A—N2	116.73 (12)	C7—N6—C5	113.53 (12)
N2A—O2A—O4Bⁱ	138.27 (10)	O6A—N6A—O6B	127.54 (13)
N2—C3—N4	100.37 (11)	O6A—N6A—N6	117.77 (12)
N2—C3—H3A	111.7	O6B—N6A—N6	114.68 (12)
N4—C3—H3A	111.7	O7—C7—N8	128.53 (15)
N2—C3—H3B	111.7	O7—C7—N6	126.62 (14)
N4—C3—H3B	111.7	N8—C7—N6	104.84 (12)
H3A—C3—H3B	109.5	C7—N8—C1	114.02 (13)
N4A—N4—C5	116.31 (11)	C7—N8—H8	121.7 (13)
N4A—N4—C3	116.26 (11)	C1—N8—H8	119.8 (12)
C5—N4—C3	112.22 (12)

N8—C1—N2—N2A	70.51 (17)	N8—C1—C5—N4	130.33 (12)
C5—C1—N2—N2A	−178.51 (12)	N2—C1—C5—N4	12.82 (14)
N8—C1—N2—C3	−115.17 (15)	N8—C1—C5—N6	14.18 (14)
C5—C1—N2—C3	−4.18 (17)	N2—C1—C5—N6	−103.33 (12)
C3—N2—N2A—O2A	3.2 (2)	N4—C5—N6—N6A	74.92 (16)
C1—N2—N2A—O2A	177.26 (13)	C1—C5—N6—N6A	−172.51 (12)
C3—N2—N2A—O2B	−177.80 (13)	N4—C5—N6—C7	−122.21 (13)
C1—N2—N2A—O2B	−3.7 (2)	C1—C5—N6—C7	−9.63 (15)
N2A—N2—C3—N4	168.27 (13)	C7—N6—N6A—O6A	11.2 (2)
C1—N2—C3—N4	−5.96 (17)	C5—N6—N6A—O6A	172.04 (12)
N2—C3—N4—N4A	−122.58 (13)	C7—N6—N6A—O6B	−169.92 (13)
N2—C3—N4—C5	14.76 (15)	C5—N6—N6A—O6B	−9.13 (18)
C5—N4—N4A—O4B	16.40 (18)	N6A—N6—C7—O7	−18.1 (2)
C3—N4—N4A—O4B	151.99 (13)	C5—N6—C7—O7	−179.87 (13)
C5—N4—N4A—O4A	−167.28 (12)	N6A—N6—C7—N8	162.60 (13)
C3—N4—N4A—O4A	−31.69 (18)	C5—N6—C7—N8	0.87 (16)
N4A—N4—C5—N6	−132.11 (12)	O7—C7—N8—C1	−169.54 (14)
C3—N4—C5—N6	90.57 (14)	N6—C7—N8—C1	9.70 (16)
N4A—N4—C5—C1	119.10 (13)	N2—C1—N8—C7	92.77 (15)
C3—N4—C5—C1	−18.23 (15)	C5—C1—N8—C7	−15.73 (16)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2Aⁱⁱⁱ	1.00	2.51	3.1902 (18)	125
C1—H1···O4A^iv	1.00	2.56	3.0407 (18)	110
C3—H3A···O4A	0.99	2.30	2.6637 (19)	100
C3—H3B···O6Bⁱ	0.99	2.45	3.3028 (19)	144
C5—H5···O2Aⁱⁱⁱ	1.00	2.56	3.2572 (19)	127
C5—H5···O2Bⁱⁱⁱ	1.00	2.29	3.2478 (18)	159
C5—H5···O4B	1.00	2.23	2.6547 (18)	104
N8—H8···O7^v	0.87 (2)	2.06 (2)	2.8940 (18)	161.9 (17)

Symmetry codes: (i) x, −y+3/2, z−1/2; (iii) x, −y+1/2, z+1/2; (iv) −x, y−1/2, −z+1/2; (v) −x+1, y−1/2, −z+1/2.

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2,4,6-Tri­nitro-2,4,6,8-tetra­aza­bi­cyclo­[3.3.0]octan-7-one

Supporting information

Key indicators

checkCIF/PLATON results

2,4,6-Trinitro-2,4,6,8-tetraazabicyclo[3.3.0]octan-7-one