3,3-Dinitro-azetidinium chloride.

In the title gem-dinitro-azetidinium chloride salt, C3H6N3O4(+)·Cl(-), the cations and anions lie on a mirror plane. The azetidine ring is virtually planar, with a mean deviation from the plane of 0.0569 Å. The dihedral angle between the two nitro groups is 90.00 (5)°. In the crystal, the ions are linked by N-H⋯Cl interactions, forming a chain along the c-axis direction, and C-H⋯O inter-actions, forming a layer parallel to (010).

Related literature

For 1,3,3-trinitro­azetidine and compounds prepared from its derivative 3,3-dinitro­azetidine, see: Archibald et al. (1990 ▶); Hiskey et al. (1992 ▶); Ma et al. (2009a ▶,b ▶, 2011 ▶); Yan et al. (2009 ▶, 2010 ▶); Gao et al. (2009 ▶). For related structures, see: Gao et al. (2010 ▶); Ma et al. (2010 ▶). For the synthesis, see: Li et al. (2004 ▶).

Experimental

Crystal data

C3H6N3O4 +·Cl−

M = 183.56

Orthorhombic,

a = 6.6807 (17) Å

b = 10.4409 (17) Å

c = 9.9707 (19) Å

V = 695.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 293 K

0.35 × 0.34 × 0.30 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.839, T max = 0.860

1968 measured reflections

708 independent reflections

696 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.055

S = 1.10

708 reflections

62 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 252 Friedel pairs

Flack parameter: 0.09 (7)

Data collection: APEX2 (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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046302/zq2187sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046302/zq2187Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046302/zq2187Isup3.cml

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

C3H6N3O4+·Cl−	Z = 4
Mr = 183.56	F(000) = 376
Orthorhombic, Cmc21	Dx = 1.753 Mg m−3
Hall symbol: C 2c -2	Mo Kα radiation, λ = 0.71073 Å
a = 6.6807 (17) Å	µ = 0.52 mm−1
b = 10.4409 (17) Å	T = 293 K
c = 9.9707 (19) Å	Block, colourless
V = 695.5 (2) Å3	0.35 × 0.34 × 0.30 mm

Bruker SMART APEXII CCD area-detector diffractometer	708 independent reflections
Radiation source: fine-focus sealed tube	696 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
phi and ω scans	θmax = 27.9°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −8→8
Tmin = 0.839, Tmax = 0.860	k = −13→12
1968 measured reflections	l = −11→13

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.021	w = 1/[σ2(Fo2) + (0.0313P)2 + 0.199P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.055	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.18 e Å−3
708 reflections	Δρmin = −0.16 e Å−3
62 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.227 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 252 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.09 (7)

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
Cl	0.0000	0.34257 (4)	0.24339 (6)	0.03211 (19)
N2	0.0000	0.14030 (15)	0.5026 (2)	0.0277 (4)
O3	0.0000	0.07128 (19)	0.7449 (3)	0.0571 (6)
C1	0.1613 (2)	0.35120 (12)	0.57848 (17)	0.0255 (3)
H1A	0.2305	0.3773	0.6596	0.031*
H1B	0.2557	0.3293	0.5081	0.031*
N3	0.0000	0.1881 (2)	0.7388 (3)	0.0354 (4)
N1	0.0000	0.44299 (15)	0.5346 (2)	0.0269 (4)
H1C	0.0000	0.4581	0.4457	0.032*
H1D	0.0000	0.5170	0.5808	0.032*
O4	0.0000	0.2614 (3)	0.8318 (2)	0.0536 (6)
O1	0.16253 (18)	0.10036 (10)	0.46749 (16)	0.0425 (4)
C2	0.0000	0.24966 (18)	0.6017 (2)	0.0217 (4)

	U11	U22	U33	U12	U13	U23
Cl	0.0359 (3)	0.0347 (3)	0.0258 (3)	0.000	0.000	0.0048 (3)
N2	0.0314 (9)	0.0207 (8)	0.0309 (11)	0.000	0.000	0.0002 (7)
O3	0.0562 (12)	0.0522 (10)	0.0629 (14)	0.000	0.000	0.0373 (12)
C1	0.0226 (7)	0.0236 (7)	0.0304 (8)	−0.0015 (5)	0.0008 (6)	−0.0013 (5)
N3	0.0232 (8)	0.0556 (11)	0.0273 (9)	0.000	0.000	0.0133 (13)
N1	0.0323 (10)	0.0202 (7)	0.0283 (9)	0.000	0.000	−0.0012 (7)
O4	0.0463 (12)	0.0904 (16)	0.0240 (9)	0.000	0.000	−0.0017 (9)
O1	0.0365 (7)	0.0362 (6)	0.0549 (9)	0.0117 (4)	−0.0002 (7)	−0.0136 (6)
C2	0.0218 (9)	0.0215 (9)	0.0217 (11)	0.000	0.000	0.0007 (7)

N2—O1i	1.2147 (14)	C1—H1B	0.9700
N2—O1	1.2147 (14)	N3—O4	1.203 (4)
N2—C2	1.510 (3)	N3—C2	1.511 (3)
O3—N3	1.221 (3)	N1—C1i	1.5073 (19)
C1—N1	1.5073 (18)	N1—H1C	0.9000
C1—C2	1.5294 (19)	N1—H1D	0.9000
C1—H1A	0.9700	C2—C1i	1.5294 (19)
O1i—N2—O1	126.74 (19)	O4—N3—C2	115.2 (2)
O1i—N2—C2	116.63 (9)	O3—N3—C2	118.0 (3)
O1—N2—C2	116.63 (9)	C1—N1—C1i	91.30 (15)
N1—C1—C2	88.89 (11)	C1—N1—H1C	113.4
N1—C1—H1A	113.8	C1—N1—H1D	113.4
C2—C1—H1A	113.8	H1C—N1—H1D	110.7
N1—C1—H1B	113.8	N2—C2—N3	105.67 (17)
C2—C1—H1B	113.8	N2—C2—C1	115.17 (13)
H1A—C1—H1B	111.1	N3—C2—C1	115.58 (13)
O4—N3—O3	126.7 (3)	C1—C2—C1i	89.62 (15)
C2—C1—N1—C1i	8.66 (17)	O3—N3—C2—N2	0.0
O1i—N2—C2—N3	89.58 (16)	O4—N3—C2—C1	51.39 (11)
O1—N2—C2—N3	−89.58 (16)	O3—N3—C2—C1	−128.61 (11)
O1i—N2—C2—C1	−141.56 (16)	O4—N3—C2—C1i	−51.39 (11)
O1—N2—C2—C1	39.3 (2)	O3—N3—C2—C1i	128.61 (11)
O1i—N2—C2—C1i	−39.3 (2)	N1—C1—C2—N2	109.30 (15)
O1—N2—C2—C1i	141.56 (16)	N1—C1—C2—N3	−126.93 (15)
O4—N3—C2—N2	180.0	N1—C1—C2—C1i	−8.53 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl	0.90	2.35	3.087 (2)	139
N1—H1D···Clii	0.90	2.19	3.0575 (19)	163
C1—H1B···O1	0.97	2.50	2.8432 (19)	100
C1—H1B···O4iii	0.97	2.58	3.543 (2)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Cl	0.90	2.35	3.087 (2)	139
N1—H1D⋯Cli	0.90	2.19	3.0575 (19)	163
C1—H1B⋯O4ii	0.97	2.58	3.543 (2)	172

Symmetry codes: (i) ; (ii) .