1-Benzoyl-3,3-dinitro-azetidine.

In the title gem-dinitro-azetidine derivative, C(10)H(9)N(3)O(5), the azetidine ring is almost planar, the maximum value of the endocyclic torsion angle being 0.92 (14)°. The gem-dinitro groups are mutually perpendicular and the dihedral angle between the azetidine and benzene rings is 46.70 (10)°

Related literature

For energetic materials based on 3,3-dinitro­azetidine, see: Archibald et al. (1990 ▶); Gao et al. (2009 ▶); Hiskey & Coburn (1994a ▶,b ▶); Ma, Yan, Li, Guan et al. (2009 ▶); Ma, Yan, Li, Song & Hu (2009 ▶); Ma, Yan, Song et al. (2009 ▶).

Experimental

Crystal data

C10H9N3O5

M = 251.20

Monoclinic,

a = 13.176 (4) Å

b = 6.2344 (19) Å

c = 13.522 (4) Å

β = 92.612 (6)°

V = 1109.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.39 × 0.27 × 0.15 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.954, T max = 0.981

5306 measured reflections

1975 independent reflections

1210 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 0.98

1975 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 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/S1600536809051290/gk2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051290/gk2242Isup2.hkl

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

C10H9N3O5	F(000) = 520
Mr = 251.20	Dx = 1.504 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 862 reflections
a = 13.176 (4) Å	θ = 3.0–21.2°
b = 6.2344 (19) Å	µ = 0.12 mm−1
c = 13.522 (4) Å	T = 296 K
β = 92.612 (6)°	Block, colorless
V = 1109.6 (6) Å3	0.39 × 0.27 × 0.15 mm
Z = 4

Bruker SMART APEXII diffractometer	1975 independent reflections
Radiation source: fine-focus sealed tube	1210 reflections with I > 2σ(I)
graphite	Rint = 0.028
phi and ω scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −15→15
Tmin = 0.954, Tmax = 0.981	k = −7→7
5306 measured reflections	l = −15→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
1975 reflections	Δρmax = 0.15 e Å−3
164 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)

Geometry. 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.

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
N3	0.68948 (11)	0.3359 (2)	0.80874 (11)	0.0468 (4)
O5	0.75063 (10)	0.01052 (19)	0.84162 (10)	0.0599 (4)
O1	0.75527 (11)	0.6527 (2)	0.99733 (12)	0.0775 (5)
O2	0.61765 (11)	0.8369 (2)	1.01338 (11)	0.0705 (5)
O3	0.44932 (11)	0.6147 (2)	0.89476 (11)	0.0713 (5)
O4	0.52323 (10)	0.8514 (2)	0.80573 (12)	0.0702 (5)
C6	0.91631 (15)	0.0829 (3)	0.71825 (16)	0.0579 (6)
H6	0.9293	−0.0078	0.7719	0.070*
C7	0.98541 (16)	0.0983 (3)	0.64582 (19)	0.0692 (6)
H7	1.0451	0.0188	0.6510	0.083*
C8	0.96726 (16)	0.2296 (3)	0.56602 (18)	0.0654 (6)
H8	1.0145	0.2398	0.5172	0.078*
C9	0.87872 (16)	0.3464 (3)	0.55826 (16)	0.0601 (6)
H9	0.8658	0.4351	0.5038	0.072*
C10	0.80912 (15)	0.3321 (3)	0.63113 (14)	0.0509 (5)
H10	0.7494	0.4115	0.6255	0.061*
C5	0.82730 (13)	0.2012 (3)	0.71215 (14)	0.0439 (5)
C4	0.75447 (13)	0.1743 (3)	0.79194 (14)	0.0444 (5)
C3	0.69359 (15)	0.5702 (3)	0.79507 (14)	0.0498 (5)
H3A	0.6629	0.6195	0.7326	0.060*
H3B	0.7607	0.6314	0.8072	0.060*
C1	0.62456 (13)	0.5904 (3)	0.88225 (13)	0.0419 (5)
C2	0.62480 (14)	0.3459 (3)	0.89365 (14)	0.0489 (5)
H2B	0.6575	0.2956	0.9551	0.059*
H2A	0.5586	0.2801	0.8821	0.059*
N1	0.66923 (14)	0.7057 (3)	0.97243 (13)	0.0541 (5)
N2	0.52333 (12)	0.6935 (3)	0.85921 (13)	0.0513 (4)

	U11	U22	U33	U12	U13	U23
N3	0.0634 (10)	0.0315 (8)	0.0468 (10)	0.0014 (7)	0.0156 (8)	0.0040 (7)
O5	0.0819 (10)	0.0343 (7)	0.0641 (9)	0.0015 (6)	0.0103 (8)	0.0088 (7)
O1	0.0730 (10)	0.0680 (10)	0.0889 (13)	−0.0016 (8)	−0.0258 (9)	0.0058 (8)
O2	0.0914 (11)	0.0603 (9)	0.0607 (10)	−0.0037 (8)	0.0135 (9)	−0.0178 (8)
O3	0.0565 (9)	0.0876 (12)	0.0710 (11)	0.0034 (8)	0.0172 (8)	0.0072 (9)
O4	0.0717 (10)	0.0584 (9)	0.0800 (11)	0.0119 (7)	−0.0017 (8)	0.0189 (8)
C6	0.0657 (13)	0.0471 (12)	0.0611 (14)	0.0105 (10)	0.0041 (12)	0.0029 (10)
C7	0.0581 (13)	0.0652 (14)	0.0848 (18)	0.0108 (11)	0.0108 (13)	−0.0071 (13)
C8	0.0668 (14)	0.0598 (13)	0.0712 (17)	−0.0057 (11)	0.0222 (12)	−0.0085 (12)
C9	0.0764 (14)	0.0533 (13)	0.0513 (13)	0.0010 (11)	0.0115 (11)	0.0033 (10)
C10	0.0579 (11)	0.0497 (12)	0.0453 (12)	0.0058 (9)	0.0050 (10)	−0.0012 (10)
C5	0.0536 (11)	0.0324 (10)	0.0454 (12)	−0.0006 (8)	0.0004 (9)	−0.0043 (9)
C4	0.0553 (11)	0.0320 (10)	0.0454 (11)	−0.0013 (9)	−0.0008 (9)	−0.0019 (9)
C3	0.0641 (12)	0.0355 (10)	0.0511 (12)	0.0046 (8)	0.0147 (10)	0.0054 (9)
C1	0.0495 (11)	0.0356 (9)	0.0407 (11)	0.0024 (8)	0.0038 (9)	0.0001 (8)
C2	0.0604 (11)	0.0393 (10)	0.0477 (12)	−0.0017 (9)	0.0101 (9)	0.0022 (9)
N1	0.0679 (12)	0.0413 (10)	0.0528 (11)	−0.0070 (9)	0.0002 (10)	0.0038 (8)
N2	0.0565 (11)	0.0492 (10)	0.0482 (10)	0.0039 (9)	0.0035 (8)	−0.0039 (8)

N3—C4	1.348 (2)	C8—H8	0.9300
N3—C2	1.462 (2)	C9—C10	1.379 (3)
N3—C3	1.474 (2)	C9—H9	0.9300
O5—C4	1.224 (2)	C10—C5	1.378 (3)
O1—N1	1.2134 (19)	C10—H10	0.9300
O2—N1	1.2133 (18)	C5—C4	1.486 (2)
O3—N2	1.2109 (19)	C3—C1	1.527 (2)
O4—N2	1.2212 (19)	C3—H3A	0.9700
C6—C7	1.371 (3)	C3—H3B	0.9700
C6—C5	1.385 (2)	C1—N2	1.500 (2)
C6—H6	0.9300	C1—N1	1.511 (2)
C7—C8	1.367 (3)	C1—C2	1.532 (2)
C7—H7	0.9300	C2—H2B	0.9700
C8—C9	1.375 (3)	C2—H2A	0.9700
C4—N3—C2	124.17 (15)	N3—C3—C1	87.62 (12)
C4—N3—C3	133.82 (14)	N3—C3—H3A	114.0
C2—N3—C3	94.70 (12)	C1—C3—H3A	114.0
C7—C6—C5	120.6 (2)	N3—C3—H3B	114.0
C7—C6—H6	119.7	C1—C3—H3B	114.0
C5—C6—H6	119.7	H3A—C3—H3B	111.2
C8—C7—C6	120.5 (2)	N2—C1—N1	105.88 (14)
C8—C7—H7	119.7	N2—C1—C3	115.48 (15)
C6—C7—H7	119.7	N1—C1—C3	116.01 (15)
C7—C8—C9	119.7 (2)	N2—C1—C2	116.42 (14)
C7—C8—H8	120.2	N1—C1—C2	113.13 (15)
C9—C8—H8	120.2	C3—C1—C2	89.82 (12)
C8—C9—C10	120.0 (2)	N3—C2—C1	87.84 (12)
C8—C9—H9	120.0	N3—C2—H2B	114.0
C10—C9—H9	120.0	C1—C2—H2B	114.0
C5—C10—C9	120.60 (18)	N3—C2—H2A	114.0
C5—C10—H10	119.7	C1—C2—H2A	114.0
C9—C10—H10	119.7	H2B—C2—H2A	111.2
C10—C5—C6	118.61 (18)	O2—N1—O1	126.33 (18)
C10—C5—C4	123.34 (16)	O2—N1—C1	118.88 (17)
C6—C5—C4	118.01 (18)	O1—N1—C1	114.78 (17)
O5—C4—N3	119.23 (17)	O3—N2—O4	125.66 (17)
O5—C4—C5	122.48 (16)	O3—N2—C1	117.90 (16)
N3—C4—C5	118.29 (15)	O4—N2—C1	116.44 (16)
C5—C6—C7—C8	−0.5 (3)	N3—C3—C1—N1	116.69 (15)
C6—C7—C8—C9	−0.3 (3)	N3—C3—C1—C2	0.88 (14)
C7—C8—C9—C10	0.5 (3)	C4—N3—C2—C1	154.51 (16)
C8—C9—C10—C5	0.0 (3)	C3—N3—C2—C1	0.92 (14)
C9—C10—C5—C6	−0.7 (3)	N2—C1—C2—N3	117.73 (15)
C9—C10—C5—C4	−178.42 (16)	N1—C1—C2—N3	−119.27 (16)
C7—C6—C5—C10	0.9 (3)	C3—C1—C2—N3	−0.88 (14)
C7—C6—C5—C4	178.79 (17)	N2—C1—N1—O2	6.0 (2)
C2—N3—C4—O5	10.7 (3)	C3—C1—N1—O2	135.59 (16)
C3—N3—C4—O5	152.76 (19)	C2—C1—N1—O2	−122.61 (16)
C2—N3—C4—C5	−170.27 (16)	N2—C1—N1—O1	−174.84 (15)
C3—N3—C4—C5	−28.2 (3)	C3—C1—N1—O1	−45.3 (2)
C10—C5—C4—O5	152.40 (18)	C2—C1—N1—O1	56.5 (2)
C6—C5—C4—O5	−25.3 (3)	N1—C1—N2—O3	−92.40 (18)
C10—C5—C4—N3	−26.6 (2)	C3—C1—N2—O3	137.76 (16)
C6—C5—C4—N3	155.63 (16)	C2—C1—N2—O3	34.3 (2)
C4—N3—C3—C1	−150.25 (19)	N1—C1—N2—O4	87.52 (18)
C2—N3—C3—C1	−0.92 (14)	C3—C1—N2—O4	−42.3 (2)
N3—C3—C1—N2	−118.56 (15)	C2—C1—N2—O4	−145.79 (16)