3,3-Dinitro-azetidinium 2-hy-droxy-benzoate.

In the title gem-dinitro-azetidinium 2-hy-droxy-benzoate salt, C(3)H(6)N(3)O(4) (+)·C(7)H(5)O(3) (-), the azetidine ring is virtually planar, with a mean deviation from the plane of 0.0242 Å. The dihedral angle between the two nitro groups is 87.5 (1)°.

Related literature

For related literature on 1,3,3-trinitro­azetidine and compounds prepared from its derivative 3,3-dinitro­azetidine, see: Archibald et al. (1990 ▶); Gao et al. (2009 ▶); Hiskey et al. (1992 ▶); Ma, Yan, Li, Guan et al. (2009 ▶); Ma, Yan, Li, Song & Hu (2009 ▶); Ma, Yan, Song et al. (2009 ▶); Ma et al. (2010 ▶); Yan et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C3H6N3O4 +·C7H5O3 −

M = 285.22

Monoclinic,

a = 11.174 (3) Å

b = 7.013 (2) Å

c = 16.661 (5) Å

β = 105.960 (5)°

V = 1255.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.36 × 0.26 × 0.19 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.955, T max = 0.976

6012 measured reflections

2222 independent reflections

1504 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.128

S = 0.99

2222 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.17 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/S1600536810043825/ng5053sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043825/ng5053Isup2.hkl

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

C3H6N3O4+·C7H5O3−	F(000) = 592
Mr = 285.22	Dx = 1.509 Mg m−3
Monoclinic, P21/n	Melting point: 379.4 K
Hall symbol: -P2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.174 (3) Å	Cell parameters from 1275 reflections
b = 7.013 (2) Å	θ = 2.5–21.9°
c = 16.661 (5) Å	µ = 0.13 mm−1
β = 105.960 (5)°	T = 296 K
V = 1255.3 (6) Å3	Block, colorless
Z = 4	0.36 × 0.26 × 0.19 mm

Bruker APEX CCD area-detector diffractometer	2222 independent reflections
Radiation source: fine-focus sealed tube	1504 reflections with I > 2σ(I)
graphite	Rint = 0.027
phi and ω scans	θmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −12→13
Tmin = 0.955, Tmax = 0.976	k = −8→8
6012 measured reflections	l = −18→19

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0797P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.002
2222 reflections	Δρmax = 0.34 e Å−3
183 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

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
O7	0.58576 (13)	0.7941 (2)	0.06388 (8)	0.0563 (4)
O6	0.46538 (12)	0.5959 (2)	0.10843 (9)	0.0629 (4)
O5	0.53637 (13)	0.2679 (2)	0.15624 (10)	0.0619 (4)
H5	0.4878	0.3566	0.1405	0.093*
C4	0.67334 (16)	0.4982 (3)	0.12215 (10)	0.0380 (5)
N1	0.36966 (14)	0.9772 (2)	0.05657 (9)	0.0447 (4)
H1D	0.3660	1.0893	0.0297	0.054*
H1C	0.4417	0.9169	0.0593	0.054*
C5	0.65122 (17)	0.3202 (3)	0.15274 (11)	0.0407 (5)
N3	0.10748 (16)	0.9419 (3)	0.10825 (12)	0.0580 (5)
C10	0.56810 (18)	0.6383 (3)	0.09534 (11)	0.0439 (5)
C3	0.34209 (17)	0.9937 (3)	0.13919 (11)	0.0471 (5)
H3B	0.3181	1.1211	0.1514	0.056*
H3A	0.4075	0.9437	0.1854	0.056*
C2	0.23289 (16)	0.8586 (3)	0.10855 (11)	0.0412 (5)
C6	0.7486 (2)	0.1923 (3)	0.18100 (11)	0.0511 (5)
H6	0.7340	0.0722	0.2000	0.061*
C1	0.25748 (18)	0.8552 (3)	0.02338 (11)	0.0479 (5)
H1A	0.2765	0.7293	0.0061	0.057*
H1B	0.1928	0.9160	−0.0201	0.057*
C9	0.79343 (18)	0.5449 (3)	0.12150 (12)	0.0501 (5)
H9	0.8089	0.6630	0.1010	0.060*
N2	0.24179 (17)	0.6717 (3)	0.15310 (13)	0.0585 (5)
O4	0.08623 (14)	1.0972 (3)	0.07553 (11)	0.0771 (5)
C7	0.8681 (2)	0.2457 (4)	0.18067 (12)	0.0595 (6)
H7	0.9340	0.1620	0.2011	0.071*
O3	0.03912 (17)	0.8537 (3)	0.13847 (15)	0.0995 (7)
C8	0.89002 (19)	0.4198 (4)	0.15066 (13)	0.0594 (6)
H8	0.9703	0.4534	0.1500	0.071*
O1	0.19839 (17)	0.5345 (3)	0.11130 (12)	0.0861 (6)
O2	0.29006 (19)	0.6747 (3)	0.22818 (11)	0.0891 (6)

	U11	U22	U33	U12	U13	U23
O7	0.0650 (10)	0.0485 (9)	0.0622 (9)	0.0038 (7)	0.0288 (7)	0.0121 (7)
O6	0.0415 (8)	0.0663 (11)	0.0854 (11)	0.0040 (7)	0.0248 (7)	0.0167 (8)
O5	0.0492 (9)	0.0573 (10)	0.0826 (11)	−0.0109 (7)	0.0237 (8)	0.0107 (8)
C4	0.0390 (10)	0.0420 (11)	0.0340 (9)	−0.0047 (8)	0.0115 (7)	−0.0025 (8)
N1	0.0432 (9)	0.0451 (10)	0.0531 (9)	0.0044 (7)	0.0256 (7)	0.0105 (7)
C5	0.0418 (11)	0.0429 (11)	0.0363 (9)	−0.0046 (9)	0.0087 (8)	−0.0011 (8)
N3	0.0432 (10)	0.0605 (13)	0.0751 (12)	−0.0041 (9)	0.0245 (9)	−0.0147 (10)
C10	0.0500 (12)	0.0425 (12)	0.0400 (10)	−0.0027 (9)	0.0140 (9)	0.0011 (9)
C3	0.0407 (11)	0.0577 (13)	0.0467 (10)	−0.0116 (9)	0.0185 (8)	−0.0046 (9)
C2	0.0330 (9)	0.0492 (12)	0.0447 (10)	−0.0038 (8)	0.0162 (8)	−0.0006 (9)
C6	0.0633 (14)	0.0489 (12)	0.0395 (10)	0.0057 (10)	0.0116 (9)	0.0042 (9)
C1	0.0484 (11)	0.0557 (13)	0.0401 (10)	0.0045 (10)	0.0131 (8)	−0.0021 (9)
C9	0.0450 (11)	0.0535 (13)	0.0546 (12)	−0.0094 (10)	0.0183 (9)	−0.0029 (10)
N2	0.0551 (11)	0.0572 (13)	0.0725 (13)	−0.0050 (9)	0.0333 (10)	0.0088 (10)
O4	0.0646 (11)	0.0716 (12)	0.0967 (13)	0.0169 (9)	0.0250 (9)	−0.0032 (10)
C7	0.0537 (14)	0.0751 (17)	0.0443 (11)	0.0211 (12)	0.0041 (10)	−0.0059 (11)
O3	0.0672 (11)	0.0869 (14)	0.173 (2)	−0.0139 (10)	0.0806 (13)	−0.0085 (13)
C8	0.0367 (11)	0.0786 (17)	0.0633 (13)	−0.0060 (11)	0.0147 (10)	−0.0108 (12)
O1	0.0896 (13)	0.0543 (11)	0.1241 (16)	−0.0227 (9)	0.0458 (11)	−0.0050 (10)
O2	0.1054 (14)	0.1075 (15)	0.0614 (11)	0.0001 (11)	0.0347 (10)	0.0311 (10)

O7—C10	1.251 (2)	C3—H3B	0.9700
O6—C10	1.261 (2)	C3—H3A	0.9700
O5—C5	1.351 (2)	C2—N2	1.496 (3)
O5—H5	0.8200	C2—C1	1.518 (3)
C4—C9	1.384 (3)	C6—C7	1.388 (3)
C4—C5	1.396 (2)	C6—H6	0.9300
C4—C10	1.503 (3)	C1—H1A	0.9700
N1—C1	1.493 (2)	C1—H1B	0.9700
N1—C3	1.495 (2)	C9—C8	1.372 (3)
N1—H1D	0.9000	C9—H9	0.9300
N1—H1C	0.9000	N2—O1	1.208 (2)
C5—C6	1.389 (3)	N2—O2	1.219 (2)
N3—O3	1.196 (2)	C7—C8	1.367 (3)
N3—O4	1.212 (2)	C7—H7	0.9300
N3—C2	1.517 (2)	C8—H8	0.9300
C3—C2	1.518 (3)
C5—O5—H5	109.5	N2—C2—C1	116.46 (16)
C9—C4—C5	118.95 (17)	N3—C2—C1	114.04 (15)
C9—C4—C10	121.59 (17)	N2—C2—C3	116.25 (16)
C5—C4—C10	119.37 (16)	N3—C2—C3	114.66 (16)
C1—N1—C3	91.18 (13)	C1—C2—C3	89.36 (14)
C1—N1—H1D	113.4	C7—C6—C5	119.3 (2)
C3—N1—H1D	113.4	C7—C6—H6	120.3
C1—N1—H1C	113.4	C5—C6—H6	120.3
C3—N1—H1C	113.4	N1—C1—C2	89.66 (13)
H1D—N1—H1C	110.7	N1—C1—H1A	113.7
O5—C5—C6	118.36 (17)	C2—C1—H1A	113.7
O5—C5—C4	121.62 (16)	N1—C1—H1B	113.7
C6—C5—C4	120.02 (17)	C2—C1—H1B	113.7
O3—N3—O4	125.8 (2)	H1A—C1—H1B	110.9
O3—N3—C2	119.7 (2)	C8—C9—C4	121.03 (19)
O4—N3—C2	114.47 (17)	C8—C9—H9	119.5
O7—C10—O6	122.29 (18)	C4—C9—H9	119.5
O7—C10—C4	119.66 (17)	O1—N2—O2	126.9 (2)
O6—C10—C4	118.00 (17)	O1—N2—C2	116.75 (19)
N1—C3—C2	89.56 (14)	O2—N2—C2	116.36 (19)
N1—C3—H3B	113.7	C8—C7—C6	120.8 (2)
C2—C3—H3B	113.7	C8—C7—H7	119.6
N1—C3—H3A	113.7	C6—C7—H7	119.6
C2—C3—H3A	113.7	C7—C8—C9	119.87 (19)
H3B—C3—H3A	111.0	C7—C8—H8	120.1
N2—C2—N3	105.92 (15)	C9—C8—H8	120.1
C9—C4—C5—O5	178.87 (17)	O5—C5—C6—C7	−177.77 (16)
C10—C4—C5—O5	2.3 (2)	C4—C5—C6—C7	1.8 (3)
C9—C4—C5—C6	−0.7 (3)	C3—N1—C1—C2	−3.71 (15)
C10—C4—C5—C6	−177.31 (16)	N2—C2—C1—N1	−115.59 (16)
C9—C4—C10—O7	7.2 (3)	N3—C2—C1—N1	120.51 (16)
C5—C4—C10—O7	−176.32 (16)	C3—C2—C1—N1	3.65 (14)
C9—C4—C10—O6	−170.31 (17)	C5—C4—C9—C8	−0.3 (3)
C5—C4—C10—O6	6.2 (2)	C10—C4—C9—C8	176.18 (17)
C1—N1—C3—C2	3.71 (14)	N3—C2—N2—O1	87.1 (2)
O3—N3—C2—N2	−1.8 (2)	C1—C2—N2—O1	−40.8 (2)
O4—N3—C2—N2	178.59 (17)	C3—C2—N2—O1	−144.22 (18)
O3—N3—C2—C1	127.6 (2)	N3—C2—N2—O2	−91.5 (2)
O4—N3—C2—C1	−52.0 (2)	C1—C2—N2—O2	140.53 (18)
O3—N3—C2—C3	−131.4 (2)	C3—C2—N2—O2	37.1 (2)
O4—N3—C2—C3	49.0 (2)	C5—C6—C7—C8	−1.9 (3)
N1—C3—C2—N2	115.79 (17)	C6—C7—C8—C9	0.9 (3)
N1—C3—C2—N3	−119.95 (17)	C4—C9—C8—C7	0.2 (3)
N1—C3—C2—C1	−3.65 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O6	0.90	2.38	2.922 (2)	118
N1—H1C···O7	0.90	1.81	2.708 (2)	179
N1—H1D···O7i	0.90	1.96	2.720 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O6	0.90	2.38	2.922 (2)	118
N1—H1C⋯O7	0.90	1.81	2.708 (2)	179
N1—H1D⋯O7i	0.90	1.96	2.720 (2)	141

Symmetry code: (i) .