2-Nitro-1,3-dinitro-oxypropane.

The title compound, C3H5N3O8, was synthesized by reacting 2-nitro-propane-1,3-diol with acetyl nitrate. The mol-ecule is bisected by a crystallograpic mirror plane. In the crystal, the mol-ecules pack in a ribbon-like fashion along the c axis, with the central nitro groups pointing in the same direction. C-H⋯O contacts apparently provide some additional packing stabilization.

Related literature

Nitrate esters are often studied for their energetic materials properties. For example, we have reported the synthesis and crystal structure of a low melting nitrate ester (Chavez, et al. 2008 ▶)·The title compound was first synthesized by Römer (1955) ▶ but no information has been reported on the crystal structure of this material. A smilar structure was reported that differs only in a nitro­oxy group at the 2-position (Espenbetov et al. 1984 ▶).

Experimental

Crystal data

C3H5N3O8

M = 211.10

Orthorhombic,

a = 14.046 (5) Å

b = 9.607 (5) Å

c = 5.903 (3) Å

V = 796.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.38 × 0.02 × 0.01 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.935, T max = 0.998

3416 measured reflections

841 independent reflections

587 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.083

S = 1.00

841 reflections

70 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004170/ld2094sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004170/ld2094Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004170/ld2094Isup3.cml

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

C3H5N3O8	F(000) = 432
Mr = 211.10	Dx = 1.760 Mg m−3
Orthorhombic, Cmc21	Mo Kα radiation, λ = 0.71073 Å
a = 14.046 (5) Å	µ = 0.18 mm−1
b = 9.607 (5) Å	T = 293 K
c = 5.903 (3) Å	Needle, colourless
V = 796.5 (7) Å3	0.38 × 0.02 × 0.01 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	841 independent reflections
Radiation source: fine focus sealed tube	587 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 26.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −17→17
Tmin = 0.935, Tmax = 0.998	k = −11→11
3416 measured reflections	l = −7→7

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) = 0.083	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0389P)2] where P = (Fo2 + 2Fc2)/3
841 reflections	(Δ/σ)max < 0.001
70 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Experimental. Acetic acid (6.25 ml) and acetic anhydride (6.25 ml) were added to a 50 ml jacketed flask. The solution was then cooled to 0 degress C and HNO3 (4.25 g, 98%) was added dropwise while maintaining the reaction temperature below 5 degrees C. The reaction was allowed to stir for 20 min. and 2-nitro-1,3-propanediol (1.51 g, 12.5 mmol) was added. After stirring for 2 h at 0 degrees C, the temperature was raised to 20 degrees C over one hour and then stirred at 20 degrees C for an additional hour The reaction mixture was then poured into 25 ml of ice water and stirred. The white solid was filtered and washed with water and air dried to give 2.19 g of crude 1. This material was then recrystallized from carbon tetrachloride to give white needles. The melting point was measured to be 68–69 degrees C. IR analysis (KBr), proton NMR analysis (300 MHz, deuterioacetone), and elemental analysis were also performed for additional characterization.

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
C1	0.5000	0.2314 (4)	0.4290 (7)	0.0314 (8)
H1	0.5000	0.1318	0.3932	0.038*
N2	0.5000	0.2530 (4)	0.6828 (6)	0.0392 (8)
O3	0.5000	0.1504 (4)	0.8026 (5)	0.0743 (10)
O4	0.5000	0.3716 (4)	0.7543 (5)	0.0606 (9)
C5	0.58746 (15)	0.3011 (3)	0.3296 (5)	0.0386 (6)
H5A	0.5877	0.2874	0.1669	0.046*
H5B	0.5839	0.4004	0.3581	0.046*
O6	0.67514 (11)	0.24806 (16)	0.4225 (4)	0.0404 (5)
N7	0.70956 (17)	0.1273 (2)	0.3130 (4)	0.0429 (6)
O8	0.65815 (14)	0.07181 (19)	0.1797 (5)	0.0614 (6)
O9	0.78766 (13)	0.0968 (2)	0.3745 (4)	0.0611 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (18)	0.028 (2)	0.032 (2)	0.000	0.000	−0.0047 (17)
N2	0.0324 (16)	0.045 (2)	0.040 (2)	0.000	0.000	−0.004 (2)
O3	0.105 (3)	0.071 (2)	0.047 (2)	0.000	0.000	0.0159 (19)
O4	0.065 (2)	0.057 (2)	0.060 (2)	0.000	0.000	−0.0235 (17)
C5	0.0322 (14)	0.0359 (14)	0.0477 (17)	0.0026 (11)	0.0018 (13)	0.0015 (14)
O6	0.0318 (9)	0.0415 (11)	0.0480 (11)	0.0025 (8)	−0.0019 (9)	−0.0094 (10)
N7	0.0355 (12)	0.0428 (14)	0.0505 (14)	0.0019 (12)	0.0096 (12)	0.0041 (13)
O8	0.0554 (13)	0.0563 (14)	0.0725 (15)	0.0030 (11)	0.0032 (14)	−0.0254 (15)
O9	0.0359 (11)	0.0679 (15)	0.0796 (17)	0.0153 (9)	0.0032 (11)	0.0177 (12)

C1—N2	1.512 (6)	C5—O6	1.441 (3)
C1—C5	1.517 (3)	C5—H5A	0.9700
C1—C5i	1.517 (3)	C5—H5B	0.9700
C1—H1	0.9800	O6—N7	1.413 (3)
N2—O3	1.213 (4)	N7—O9	1.192 (3)
N2—O4	1.215 (4)	N7—O8	1.194 (3)
N2—C1—C5	108.8 (2)	O6—C5—H5A	109.0
N2—C1—C5i	108.8 (2)	C1—C5—H5A	109.0
C5—C1—C5i	108.2 (3)	O6—C5—H5B	109.0
N2—C1—H1	110.3	C1—C5—H5B	109.0
C5—C1—H1	110.3	H5A—C5—H5B	107.8
C5i—C1—H1	110.3	N7—O6—C5	114.1 (2)
O3—N2—O4	124.0 (4)	O9—N7—O8	130.4 (2)
O3—N2—C1	117.8 (3)	O9—N7—O6	112.1 (2)
O4—N2—C1	118.2 (3)	O8—N7—O6	117.5 (2)
O6—C5—C1	112.9 (2)
C5—C1—N2—O3	−121.2 (2)	C5i—C1—C5—O6	176.71 (15)
C5i—C1—N2—O3	121.2 (2)	C1—C5—O6—N7	85.4 (3)
C5—C1—N2—O4	58.8 (2)	C5—O6—N7—O9	171.0 (2)
C5i—C1—N2—O4	−58.8 (2)	C5—O6—N7—O8	−9.7 (3)
N2—C1—C5—O6	58.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O4ii	0.97	2.56	3.405 (5)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O4i	0.97	2.56	3.405 (5)	145

Symmetry code: (i) .