1-(2,4-Dinitro-phen-yl)-3,3-dinitro-azetidine.

In the title compound, C(9)H(7)N(5)O(8), the dihedral angle between the mean plane of the azetidine ring and that of the benzene ring is 26.1 (1)°; the planes of the two nitro groups of the azetidine ring are aligned at 88.7 (1)°.

Related literature

Highly nitrated small-ring heterocycles are good candidates for energetic materials because of the increased performance from the additional energy release upon opening of the strained ring system during decomposition, see: Frumkin et al. (1999 ▶). Azetidine-based explosives, such as 1,3,3-trinitro­azetidine (TNAZ) demonstrate excellent performance, see: Archibald et al., (1990 ▶); Hiskey & Coburn (1994a ▶,b ▶). The title compound is a derivative of 3,3-dinitro­azetidine (DNAZ) (Hiskey et al., 1992 ▶, 1993 ▶), which is a derivative of TNAZ. For the use of DNAZ in the preparation of a variety of solid energetic compounds, see: Ma et al. (2009a ▶,b ▶,c ▶); Gao et al. (2009 ▶).

Experimental

Crystal data

C9H7N5O8

M = 313.20

Monoclinic,

a = 8.113 (2) Å

b = 10.676 (3) Å

c = 14.398 (4) Å

β = 104.681 (4)°

V = 1206.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.31 × 0.26 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

5860 measured reflections

2140 independent reflections

1670 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.118

S = 1.20

2140 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049861/ng2691sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049861/ng2691Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H7N5O8	F(000) = 640
Mr = 313.20	Dx = 1.724 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1904 reflections
a = 8.113 (2) Å	θ = 2.4–26.0°
b = 10.676 (3) Å	µ = 0.15 mm−1
c = 14.398 (4) Å	T = 293 K
β = 104.681 (4)°	Block, yellow
V = 1206.3 (6) Å3	0.31 × 0.26 × 0.20 mm
Z = 4

Bruker APEXII diffractometer	1670 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
graphite	θmax = 25.1°, θmin = 2.4°
φ and ω scans	h = −9→9
5860 measured reflections	k = −11→12
2140 independent reflections	l = −17→17

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.063P)2 + 0.0921P] where P = (Fo2 + 2Fc2)/3
2140 reflections	(Δ/σ)max = 0.028
199 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O2	0.56725 (18)	0.14099 (15)	0.95776 (10)	0.0576 (4)
N1	0.06769 (18)	0.16834 (14)	0.89752 (10)	0.0360 (4)
C4	−0.0303 (2)	0.25527 (16)	0.92696 (11)	0.0324 (4)
O8	−0.18514 (19)	0.22095 (15)	0.72839 (10)	0.0566 (4)
N2	0.4618 (2)	0.14859 (15)	0.88135 (11)	0.0419 (4)
C9	−0.1501 (2)	0.33688 (17)	0.86745 (11)	0.0334 (4)
N3	0.3038 (2)	−0.04265 (16)	0.84420 (11)	0.0435 (4)
N5	−0.20374 (19)	0.32296 (17)	0.76316 (11)	0.0429 (4)
C1	0.1375 (2)	0.16202 (18)	0.81278 (12)	0.0376 (4)
H1A	0.1660	0.2430	0.7906	0.045*
H1B	0.0689	0.1131	0.7602	0.045*
C3	0.2168 (2)	0.10713 (18)	0.96128 (12)	0.0384 (4)
H3B	0.1908	0.0288	0.9886	0.046*
H3A	0.2834	0.1618	1.0105	0.046*
N4	−0.2936 (2)	0.53426 (18)	1.04331 (15)	0.0556 (5)
C7	−0.2070 (2)	0.43720 (19)	1.00353 (13)	0.0411 (5)
O3	0.4390 (2)	−0.07976 (16)	0.83333 (12)	0.0679 (5)
C6	−0.0999 (2)	0.35558 (19)	1.06406 (13)	0.0441 (5)
H6	−0.0866	0.3606	1.1300	0.053*
C2	0.2905 (2)	0.09108 (16)	0.87430 (12)	0.0340 (4)
C8	−0.2340 (2)	0.42800 (18)	0.90514 (13)	0.0388 (4)
H8	−0.3082	0.4828	0.8648	0.047*
O1	0.4830 (2)	0.19814 (17)	0.80972 (11)	0.0655 (5)
O7	−0.2721 (2)	0.41195 (17)	0.71504 (11)	0.0671 (5)
O6	−0.3804 (2)	0.61021 (15)	0.98923 (15)	0.0718 (5)
O4	0.1762 (2)	−0.10369 (15)	0.83337 (12)	0.0678 (5)
C5	−0.0131 (2)	0.26685 (19)	1.02664 (12)	0.0407 (5)
H5	0.0596	0.2125	1.0683	0.049*
O5	−0.2740 (3)	0.5369 (2)	1.13090 (13)	0.0877 (7)

	U11	U22	U33	U12	U13	U23
O2	0.0396 (8)	0.0687 (11)	0.0560 (9)	−0.0018 (7)	−0.0034 (7)	0.0035 (7)
N1	0.0336 (8)	0.0430 (9)	0.0315 (7)	0.0082 (7)	0.0083 (6)	0.0019 (6)
C4	0.0289 (9)	0.0349 (10)	0.0344 (9)	−0.0039 (7)	0.0098 (7)	−0.0011 (7)
O8	0.0486 (9)	0.0709 (11)	0.0446 (8)	0.0096 (8)	0.0012 (6)	−0.0167 (7)
N2	0.0366 (9)	0.0427 (9)	0.0457 (9)	0.0007 (7)	0.0092 (7)	0.0018 (7)
C9	0.0295 (9)	0.0389 (10)	0.0311 (8)	−0.0015 (8)	0.0062 (7)	−0.0005 (7)
N3	0.0490 (10)	0.0384 (9)	0.0433 (9)	0.0025 (8)	0.0123 (7)	−0.0007 (7)
N5	0.0306 (8)	0.0574 (11)	0.0387 (9)	0.0037 (8)	0.0050 (7)	0.0027 (8)
C1	0.0342 (10)	0.0451 (11)	0.0338 (9)	0.0067 (8)	0.0089 (7)	0.0017 (8)
C3	0.0375 (10)	0.0404 (11)	0.0364 (9)	0.0059 (8)	0.0075 (7)	0.0039 (8)
N4	0.0443 (10)	0.0497 (12)	0.0779 (13)	−0.0058 (9)	0.0253 (9)	−0.0222 (10)
C7	0.0352 (10)	0.0414 (11)	0.0497 (11)	−0.0052 (8)	0.0164 (8)	−0.0131 (9)
O3	0.0609 (10)	0.0625 (11)	0.0811 (11)	0.0189 (8)	0.0196 (8)	−0.0179 (8)
C6	0.0430 (11)	0.0556 (13)	0.0356 (9)	−0.0058 (9)	0.0135 (8)	−0.0069 (9)
C2	0.0320 (9)	0.0330 (10)	0.0359 (9)	0.0019 (7)	0.0068 (7)	0.0003 (7)
C8	0.0309 (9)	0.0364 (10)	0.0483 (10)	−0.0013 (8)	0.0086 (8)	0.0015 (8)
O1	0.0474 (9)	0.0908 (13)	0.0596 (9)	−0.0145 (8)	0.0159 (7)	0.0171 (8)
O7	0.0700 (11)	0.0777 (12)	0.0478 (8)	0.0224 (9)	0.0043 (7)	0.0165 (8)
O6	0.0689 (11)	0.0460 (10)	0.1116 (14)	0.0094 (9)	0.0432 (10)	−0.0049 (10)
O4	0.0725 (11)	0.0498 (10)	0.0845 (11)	−0.0217 (8)	0.0263 (9)	−0.0118 (8)
C5	0.0397 (10)	0.0480 (12)	0.0339 (10)	0.0030 (9)	0.0083 (8)	0.0032 (8)
O5	0.0877 (13)	0.1094 (16)	0.0693 (11)	0.0103 (11)	0.0260 (10)	−0.0450 (11)

O2—N2	1.2133 (19)	C1—C2	1.530 (2)
N1—C4	1.358 (2)	C1—H1A	0.9700
N1—C1	1.471 (2)	C1—H1B	0.9700
N1—C3	1.473 (2)	C3—C2	1.528 (3)
C4—C5	1.412 (2)	C3—H3B	0.9700
C4—C9	1.420 (2)	C3—H3A	0.9700
O8—N5	1.224 (2)	N4—O6	1.217 (2)
N2—O1	1.209 (2)	N4—O5	1.231 (2)
N2—C2	1.499 (2)	N4—C7	1.449 (3)
C9—C8	1.375 (3)	C7—C6	1.375 (3)
C9—N5	1.461 (2)	C7—C8	1.381 (3)
N3—O4	1.199 (2)	C6—C5	1.370 (3)
N3—O3	1.213 (2)	C6—H6	0.9300
N3—C2	1.504 (2)	C8—H8	0.9300
N5—O7	1.223 (2)	C5—H5	0.9300
C4—N1—C1	132.01 (15)	C2—C3—H3B	113.9
C4—N1—C3	124.20 (14)	N1—C3—H3A	113.9
C1—N1—C3	93.91 (13)	C2—C3—H3A	113.9
N1—C4—C5	117.53 (15)	H3B—C3—H3A	111.1
N1—C4—C9	126.61 (15)	O6—N4—O5	122.96 (19)
C5—C4—C9	115.86 (16)	O6—N4—C7	118.91 (19)
O1—N2—O2	125.62 (17)	O5—N4—C7	118.1 (2)
O1—N2—C2	116.82 (15)	C6—C7—C8	121.05 (18)
O2—N2—C2	117.57 (16)	C6—C7—N4	119.64 (18)
C8—C9—C4	121.83 (16)	C8—C7—N4	119.31 (18)
C8—C9—N5	115.41 (15)	C5—C6—C7	119.63 (17)
C4—C9—N5	122.54 (16)	C5—C6—H6	120.2
O4—N3—O3	125.76 (19)	C7—C6—H6	120.2
O4—N3—C2	115.52 (16)	N2—C2—N3	105.99 (14)
O3—N3—C2	118.72 (17)	N2—C2—C3	116.55 (14)
O7—N5—O8	123.01 (16)	N3—C2—C3	114.47 (15)
O7—N5—C9	118.51 (17)	N2—C2—C1	116.00 (15)
O8—N5—C9	118.39 (15)	N3—C2—C1	114.20 (14)
N1—C1—C2	88.22 (12)	C3—C2—C1	89.46 (13)
N1—C1—H1A	113.9	C9—C8—C7	119.30 (17)
C2—C1—H1A	113.9	C9—C8—H8	120.3
N1—C1—H1B	113.9	C7—C8—H8	120.4
C2—C1—H1B	113.9	C6—C5—C4	122.15 (17)
H1A—C1—H1B	111.1	C6—C5—H5	118.9
N1—C3—C2	88.23 (12)	C4—C5—H5	118.9
N1—C3—H3B	113.9
C1—N1—C4—C5	−151.31 (18)	O1—N2—C2—C3	−140.71 (18)
C3—N1—C4—C5	−15.0 (3)	O2—N2—C2—C3	39.7 (2)
C1—N1—C4—C9	28.7 (3)	O1—N2—C2—C1	−37.3 (2)
C3—N1—C4—C9	165.05 (17)	O2—N2—C2—C1	143.13 (16)
N1—C4—C9—C8	−175.18 (17)	O4—N3—C2—N2	−178.93 (15)
C5—C4—C9—C8	4.9 (3)	O3—N3—C2—N2	1.3 (2)
N1—C4—C9—N5	10.4 (3)	O4—N3—C2—C3	51.2 (2)
C5—C4—C9—N5	−169.55 (16)	O3—N3—C2—C3	−128.56 (18)
C8—C9—N5—O7	23.2 (2)	O4—N3—C2—C1	−50.0 (2)
C4—C9—N5—O7	−162.06 (18)	O3—N3—C2—C1	130.29 (18)
C8—C9—N5—O8	−153.55 (17)	N1—C3—C2—N2	122.10 (16)
C4—C9—N5—O8	21.2 (2)	N1—C3—C2—N3	−113.44 (15)
C4—N1—C1—C2	148.25 (19)	N1—C3—C2—C1	3.06 (14)
C3—N1—C1—C2	3.19 (14)	N1—C1—C2—N2	−122.59 (15)
C4—N1—C3—C2	−152.23 (17)	N1—C1—C2—N3	113.68 (16)
C1—N1—C3—C2	−3.19 (14)	N1—C1—C2—C3	−3.07 (14)
O6—N4—C7—C6	175.89 (19)	C4—C9—C8—C7	−2.9 (3)
O5—N4—C7—C6	−3.2 (3)	N5—C9—C8—C7	171.93 (16)
O6—N4—C7—C8	−4.3 (3)	C6—C7—C8—C9	−1.1 (3)
O5—N4—C7—C8	176.56 (19)	N4—C7—C8—C9	179.16 (17)
C8—C7—C6—C5	2.7 (3)	C7—C6—C5—C4	−0.4 (3)
N4—C7—C6—C5	−177.53 (18)	N1—C4—C5—C6	176.83 (18)
O1—N2—C2—N3	90.61 (19)	C9—C4—C5—C6	−3.2 (3)
O2—N2—C2—N3	−88.97 (19)