(1R*,2S*)-2-Nitro-1-(4-nitro-phen-yl)propanol.

The title compound, C(9)H(10)N(2)O(5), presents a racemic mixture of two enanti-omeric diastereomers. In the crystal, mol-ecules assemble into zigzag chains parallel to the b axis [C(6) motif] due to the formation of elongated O-H⋯O(N) hydrogen bonds. Of inter-est is the fact that only the aliphatic nitro group is involved in hydrogen bonding and it adopts a gauche conformation with respect to the OH group.

Related literature

For the preparation and synthetic utilities of 2-nitro­ethanols, see: Palomo et al. (2005 ▶); Palomo (2007 ▶). For the structure of the closely related 1-(anthracen-9-yl)-2-nitro­ethanol, see: Niazimbetova et al. (1998 ▶). For spectroscopic data and chemical properties of the title compound, see: Blay et al. (2008 ▶). For hydrogen-bond graph-set notation, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C9H10N2O5

M = 226.19

Monoclinic,

a = 7.4013 (15) Å

b = 10.504 (2) Å

c = 13.681 (3) Å

β = 100.465 (4)°

V = 1046.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.40 × 0.28 × 0.14 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.954, T max = 0.984

5155 measured reflections

1868 independent reflections

1502 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.05

1868 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812007775/hg5165sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007775/hg5165Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007775/hg5165Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812007775/hg5165Isup4.cml

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

C9H10N2O5	F(000) = 472
Mr = 226.19	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1711 reflections
a = 7.4013 (15) Å	θ = 2.5–24.3°
b = 10.504 (2) Å	µ = 0.12 mm−1
c = 13.681 (3) Å	T = 296 K
β = 100.465 (4)°	Prism, colourless
V = 1046.0 (4) Å3	0.40 × 0.28 × 0.14 mm
Z = 4

Bruker APEXII diffractometer	1868 independent reflections
Radiation source: fine-focus sealed tube	1502 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.333 pixels mm-1	θmax = 25.1°, θmin = 2.5°
φ and ω scans	h = −8→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.954, Tmax = 0.984	l = −14→16
5155 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3436P] where P = (Fo2 + 2Fc2)/3
1868 reflections	(Δ/σ)max < 0.001
150 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.16 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
N1	0.1671 (2)	−0.04487 (15)	0.18274 (12)	0.0528 (4)
N2	0.3598 (3)	0.67086 (16)	0.05631 (16)	0.0611 (5)
O1	0.2260 (2)	−0.09283 (15)	0.26305 (12)	0.0718 (5)
O2	0.0497 (3)	−0.09303 (15)	0.12111 (11)	0.0800 (6)
O3	0.0003 (3)	0.17439 (15)	0.21466 (14)	0.0757 (6)
O4	0.4510 (3)	0.72894 (16)	0.12539 (14)	0.0886 (6)
O5	0.3235 (3)	0.71279 (16)	−0.02787 (15)	0.0872 (6)
C1	0.3609 (4)	0.0580 (2)	0.07942 (18)	0.0722 (7)
H1A	0.4478	−0.0088	0.1005	0.108*
H1B	0.4254	0.1345	0.0684	0.108*
H1C	0.2816	0.0334	0.0188	0.108*
C2	0.2477 (3)	0.08152 (17)	0.15862 (16)	0.0522 (5)
H2	0.3297	0.1121	0.2184	0.063*
C3	0.0905 (3)	0.17561 (18)	0.13254 (15)	0.0512 (5)
H3A	0.0060	0.1456	0.0734	0.061*
C4	0.1629 (3)	0.30631 (17)	0.11196 (14)	0.0464 (5)
C5	0.2240 (3)	0.3894 (2)	0.18973 (15)	0.0551 (5)
H5	0.2211	0.3644	0.2546	0.066*
C6	0.2890 (3)	0.50863 (19)	0.17205 (15)	0.0555 (5)
H6	0.3295	0.5643	0.2243	0.067*
C7	0.2926 (3)	0.54335 (17)	0.07561 (15)	0.0489 (5)
C8	0.2320 (3)	0.46360 (18)	−0.00374 (15)	0.0522 (5)
H8	0.2347	0.4892	−0.0685	0.063*
C9	0.1676 (3)	0.34498 (18)	0.01569 (15)	0.0520 (5)
H9	0.1266	0.2898	−0.0368	0.062*
H3	−0.076 (4)	0.230 (3)	0.209 (2)	0.103 (11)*

	U11	U22	U33	U12	U13	U23
N1	0.0716 (11)	0.0402 (9)	0.0517 (10)	−0.0058 (8)	0.0245 (9)	−0.0030 (8)
N2	0.0612 (11)	0.0396 (10)	0.0843 (14)	−0.0007 (8)	0.0185 (10)	0.0046 (10)
O1	0.0958 (12)	0.0593 (10)	0.0614 (10)	−0.0052 (8)	0.0171 (8)	0.0150 (8)
O2	0.1145 (14)	0.0619 (10)	0.0603 (10)	−0.0379 (10)	0.0069 (9)	−0.0026 (8)
O3	0.0893 (12)	0.0504 (9)	0.1043 (14)	0.0075 (9)	0.0623 (11)	0.0127 (9)
O4	0.1091 (14)	0.0488 (10)	0.1031 (14)	−0.0220 (9)	0.0061 (11)	−0.0073 (9)
O5	0.1046 (14)	0.0596 (10)	0.0953 (13)	−0.0183 (9)	0.0122 (11)	0.0244 (9)
C1	0.0846 (16)	0.0519 (13)	0.0924 (17)	0.0049 (11)	0.0487 (14)	0.0075 (12)
C2	0.0625 (12)	0.0343 (10)	0.0650 (13)	−0.0074 (9)	0.0251 (10)	−0.0013 (9)
C3	0.0542 (11)	0.0440 (11)	0.0587 (12)	−0.0049 (9)	0.0191 (9)	0.0039 (9)
C4	0.0475 (10)	0.0385 (10)	0.0560 (11)	0.0008 (8)	0.0168 (9)	0.0023 (8)
C5	0.0657 (13)	0.0511 (12)	0.0531 (12)	−0.0037 (10)	0.0233 (10)	0.0009 (9)
C6	0.0598 (12)	0.0486 (11)	0.0595 (13)	−0.0036 (9)	0.0151 (10)	−0.0098 (10)
C7	0.0461 (10)	0.0336 (10)	0.0695 (13)	0.0013 (8)	0.0176 (9)	0.0020 (9)
C8	0.0607 (12)	0.0430 (11)	0.0548 (12)	0.0012 (9)	0.0155 (9)	0.0067 (9)
C9	0.0614 (12)	0.0405 (11)	0.0548 (12)	−0.0028 (9)	0.0126 (9)	−0.0021 (9)

N1—O2	1.206 (2)	C2—H2	0.9800
N1—O1	1.215 (2)	C3—C4	1.519 (3)
N1—C2	1.516 (2)	C3—H3A	0.9800
N2—O5	1.217 (2)	C4—C9	1.385 (3)
N2—O4	1.220 (2)	C4—C5	1.387 (3)
N2—C7	1.469 (2)	C5—C6	1.378 (3)
O3—C3	1.407 (2)	C5—H5	0.9300
O3—H3	0.80 (3)	C6—C7	1.374 (3)
C1—C2	1.505 (3)	C6—H6	0.9300
C1—H1A	0.9600	C7—C8	1.380 (3)
C1—H1B	0.9600	C8—C9	1.377 (3)
C1—H1C	0.9600	C8—H8	0.9300
C2—C3	1.519 (3)	C9—H9	0.9300
O2—N1—O1	123.54 (17)	O3—C3—H3A	109.4
O2—N1—C2	118.50 (17)	C4—C3—H3A	109.4
O1—N1—C2	117.96 (17)	C2—C3—H3A	109.4
O5—N2—O4	123.24 (19)	C9—C4—C5	118.93 (17)
O5—N2—C7	118.44 (19)	C9—C4—C3	120.81 (17)
O4—N2—C7	118.31 (19)	C5—C4—C3	120.26 (18)
C3—O3—H3	110 (2)	C6—C5—C4	120.86 (19)
C2—C1—H1A	109.5	C6—C5—H5	119.6
C2—C1—H1B	109.5	C4—C5—H5	119.6
H1A—C1—H1B	109.5	C7—C6—C5	118.55 (19)
C2—C1—H1C	109.5	C7—C6—H6	120.7
H1A—C1—H1C	109.5	C5—C6—H6	120.7
H1B—C1—H1C	109.5	C6—C7—C8	122.29 (18)
C1—C2—N1	107.80 (16)	C6—C7—N2	118.74 (18)
C1—C2—C3	116.12 (18)	C8—C7—N2	118.96 (18)
N1—C2—C3	107.79 (16)	C9—C8—C7	118.15 (19)
C1—C2—H2	108.3	C9—C8—H8	120.9
N1—C2—H2	108.3	C7—C8—H8	120.9
C3—C2—H2	108.3	C8—C9—C4	121.22 (19)
O3—C3—C4	113.00 (16)	C8—C9—H9	119.4
O3—C3—C2	105.12 (16)	C4—C9—H9	119.4
C4—C3—C2	110.52 (16)
O2—N1—C2—C1	−69.5 (2)	C3—C4—C5—C6	−179.58 (18)
O1—N1—C2—C1	109.8 (2)	C4—C5—C6—C7	−0.2 (3)
O2—N1—C2—C3	56.6 (2)	C5—C6—C7—C8	0.6 (3)
O1—N1—C2—C3	−124.2 (2)	C5—C6—C7—N2	179.34 (18)
C1—C2—C3—O3	176.23 (17)	O5—N2—C7—C6	−162.9 (2)
N1—C2—C3—O3	55.2 (2)	O4—N2—C7—C6	17.9 (3)
C1—C2—C3—C4	−61.5 (2)	O5—N2—C7—C8	15.9 (3)
N1—C2—C3—C4	177.48 (16)	O4—N2—C7—C8	−163.3 (2)
O3—C3—C4—C9	−146.5 (2)	C6—C7—C8—C9	−0.6 (3)
C2—C3—C4—C9	96.0 (2)	N2—C7—C8—C9	−179.31 (17)
O3—C3—C4—C5	32.9 (3)	C7—C8—C9—C4	0.2 (3)
C2—C3—C4—C5	−84.6 (2)	C5—C4—C9—C8	0.2 (3)
C9—C4—C5—C6	−0.1 (3)	C3—C4—C9—C8	179.61 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.80 (3)	2.24 (3)	3.010 (2)	162 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.80 (3)	2.24 (3)	3.010 (2)	162 (3)

Symmetry code: (i) .