2-(2-Nitro-phen-yl)-1,3-dioxan-5-ol.

In the title compound, C(10)H(11)NO(5), the six-membered 1,3-dioxane ring displays a chair conformation, with the hydr-oxy and 2-nitro-phenyl groups in equatorial positions, which minimizes steric hindrance. In the crystal, mol-ecules are linked into chains along the b axis by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For background to the condensation of glycerol with aldehydes and ketones to [1,3]dioxan-5-ols and [1,3]dioxolan-4-yl-methanols, see: Deutsch et al. (2007 ▶); Hill et al. (1928 ▶). Six-membered ring acetals are potential precursors for the production of the green platform chemicals, e.g. 1,3-dihydroxy­acetone and 1,3-propane­diol, see: Wang et al. (2003 ▶, 2009 ▶). For a related structure, see: Li et al. (2009 ▶).

Experimental

Crystal data

C10H11NO5

M = 225.20

Monoclinic,

a = 8.0166 (4) Å

b = 10.6499 (5) Å

c = 12.4109 (6) Å

β = 101.221 (1)°

V = 1039.34 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.35 × 0.19 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.960, T max = 0.986

9906 measured reflections

2346 independent reflections

1466 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.00

2346 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043402/pv2219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043402/pv2219Isup2.hkl

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

C10H11NO5	F(000) = 472
Mr = 225.20	Dx = 1.439 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6214 reflections
a = 8.0166 (4) Å	θ = 3.2–27.4°
b = 10.6499 (5) Å	µ = 0.12 mm−1
c = 12.4109 (6) Å	T = 296 K
β = 101.221 (1)°	Chunk, colorless
V = 1039.34 (9) Å3	0.35 × 0.19 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2346 independent reflections
Radiation source: rolling anode	1466 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.2°
ω scans	h = −9→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.960, Tmax = 0.986	l = −16→15
9906 measured reflections

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.330P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2346 reflections	Δρmax = 0.18 e Å−3
147 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: 0.0152 (19)

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
O3	0.65238 (15)	0.68340 (10)	0.28615 (9)	0.0558 (3)
C5	0.78112 (19)	0.53115 (14)	0.41276 (12)	0.0456 (4)
O2	0.70918 (18)	0.73226 (11)	0.47090 (10)	0.0693 (4)
N1	0.89732 (19)	0.48237 (15)	0.24515 (13)	0.0616 (4)
C9	0.8397 (2)	0.31608 (16)	0.36545 (16)	0.0632 (5)
H9	0.8762	0.2600	0.3174	0.076*
C3	0.7680 (2)	0.66933 (14)	0.38712 (13)	0.0485 (4)
H3	0.8797	0.7022	0.3804	0.058*
C10	0.83678 (19)	0.44328 (15)	0.34425 (13)	0.0488 (4)
C6	0.7294 (2)	0.48360 (17)	0.50467 (14)	0.0588 (5)
H6	0.6903	0.5386	0.5524	0.071*
C8	0.7884 (3)	0.27296 (19)	0.45772 (18)	0.0716 (6)
H8	0.7905	0.1874	0.4730	0.086*
O4	0.9752 (2)	0.57938 (16)	0.24619 (14)	0.0940 (5)
O1	0.6154 (2)	1.02233 (13)	0.3183 (2)	0.1241 (8)
H101	0.5292	1.0497	0.2787	0.149*
C2	0.7052 (3)	0.86500 (18)	0.45027 (19)	0.0837 (7)
H2A	0.8195	0.8949	0.4502	0.100*
H2B	0.6628	0.9084	0.5082	0.100*
C1	0.5922 (3)	0.89338 (17)	0.3408 (2)	0.0783 (7)
H1	0.4730	0.8775	0.3446	0.094*
C4	0.6432 (3)	0.81319 (17)	0.25365 (17)	0.0706 (6)
H4A	0.5610	0.8228	0.1856	0.085*
H4B	0.7531	0.8403	0.2408	0.085*
C7	0.7342 (3)	0.3565 (2)	0.52745 (16)	0.0700 (5)
H7	0.7004	0.3274	0.5905	0.084*
O5	0.8708 (2)	0.41251 (17)	0.16609 (13)	0.1034 (6)

	U11	U22	U33	U12	U13	U23
O3	0.0629 (7)	0.0404 (6)	0.0568 (7)	−0.0064 (5)	−0.0067 (5)	0.0055 (5)
C5	0.0449 (8)	0.0405 (9)	0.0484 (8)	0.0015 (6)	0.0018 (7)	−0.0013 (7)
O2	0.0931 (9)	0.0483 (7)	0.0641 (8)	0.0167 (6)	0.0093 (7)	−0.0112 (6)
N1	0.0601 (9)	0.0607 (10)	0.0658 (10)	0.0037 (7)	0.0165 (7)	−0.0066 (8)
C9	0.0663 (11)	0.0415 (10)	0.0760 (12)	0.0095 (8)	−0.0007 (9)	−0.0071 (9)
C3	0.0503 (9)	0.0401 (9)	0.0515 (9)	0.0013 (7)	0.0008 (7)	−0.0043 (7)
C10	0.0465 (8)	0.0448 (9)	0.0529 (9)	0.0027 (7)	0.0044 (7)	−0.0020 (7)
C6	0.0661 (11)	0.0551 (11)	0.0547 (10)	0.0040 (8)	0.0102 (8)	0.0037 (8)
C8	0.0802 (13)	0.0446 (11)	0.0809 (13)	−0.0019 (9)	−0.0068 (11)	0.0126 (10)
O4	0.1066 (12)	0.0895 (12)	0.0969 (11)	−0.0285 (10)	0.0472 (9)	−0.0076 (9)
O1	0.0894 (11)	0.0398 (9)	0.214 (2)	0.0013 (7)	−0.0431 (13)	0.0144 (10)
C2	0.0989 (16)	0.0438 (11)	0.0996 (16)	0.0156 (10)	−0.0026 (13)	−0.0185 (10)
C1	0.0624 (11)	0.0373 (10)	0.1237 (18)	0.0046 (8)	−0.0106 (12)	0.0036 (11)
C4	0.0676 (12)	0.0457 (10)	0.0879 (14)	−0.0100 (8)	−0.0114 (10)	0.0209 (10)
C7	0.0750 (13)	0.0679 (13)	0.0638 (11)	−0.0063 (10)	0.0057 (10)	0.0205 (10)
O5	0.1424 (15)	0.1019 (13)	0.0717 (9)	−0.0136 (11)	0.0352 (10)	−0.0322 (9)

O3—C3	1.4142 (18)	C6—C7	1.382 (3)
O3—C4	1.438 (2)	C6—H6	0.9300
C5—C6	1.383 (2)	C8—C7	1.369 (3)
C5—C10	1.395 (2)	C8—H8	0.9300
C5—C3	1.505 (2)	O1—C1	1.421 (2)
O2—C3	1.394 (2)	O1—H101	0.8200
O2—C2	1.436 (2)	C2—C1	1.510 (3)
N1—O4	1.206 (2)	C2—H2A	0.9700
N1—O5	1.2167 (19)	C2—H2B	0.9700
N1—C10	1.468 (2)	C1—C4	1.496 (3)
C9—C8	1.369 (3)	C1—H1	0.9800
C9—C10	1.379 (2)	C4—H4A	0.9700
C9—H9	0.9300	C4—H4B	0.9700
C3—H3	0.9800	C7—H7	0.9300
C3—O3—C4	109.84 (12)	C9—C8—H8	120.2
C6—C5—C10	116.10 (15)	C7—C8—H8	120.2
C6—C5—C3	120.83 (15)	C1—O1—H101	109.5
C10—C5—C3	123.00 (15)	O2—C2—C1	110.25 (16)
C3—O2—C2	109.83 (15)	O2—C2—H2A	109.6
O4—N1—O5	122.79 (18)	C1—C2—H2A	109.6
O4—N1—C10	119.27 (15)	O2—C2—H2B	109.6
O5—N1—C10	117.90 (16)	C1—C2—H2B	109.6
C8—C9—C10	119.50 (18)	H2A—C2—H2B	108.1
C8—C9—H9	120.3	O1—C1—C4	110.2 (2)
C10—C9—H9	120.3	O1—C1—C2	106.94 (17)
O2—C3—O3	110.58 (13)	C4—C1—C2	109.60 (16)
O2—C3—C5	109.41 (14)	O1—C1—H1	110.0
O3—C3—C5	107.32 (12)	C4—C1—H1	110.0
O2—C3—H3	109.8	C2—C1—H1	110.0
O3—C3—H3	109.8	O3—C4—C1	110.63 (17)
C5—C3—H3	109.8	O3—C4—H4A	109.5
C9—C10—C5	122.56 (16)	C1—C4—H4A	109.5
C9—C10—N1	116.26 (16)	O3—C4—H4B	109.5
C5—C10—N1	121.19 (15)	C1—C4—H4B	109.5
C7—C6—C5	121.76 (18)	H4A—C4—H4B	108.1
C7—C6—H6	119.1	C8—C7—C6	120.43 (19)
C5—C6—H6	119.1	C8—C7—H7	119.8
C9—C8—C7	119.65 (18)	C6—C7—H7	119.8
C2—O2—C3—O3	−65.20 (18)	O5—N1—C10—C9	33.6 (2)
C2—O2—C3—C5	176.81 (14)	O4—N1—C10—C5	35.4 (2)
C4—O3—C3—O2	64.54 (18)	O5—N1—C10—C5	−146.86 (17)
C4—O3—C3—C5	−176.20 (14)	C10—C5—C6—C7	0.5 (2)
C6—C5—C3—O2	3.4 (2)	C3—C5—C6—C7	177.47 (16)
C10—C5—C3—O2	−179.88 (14)	C10—C9—C8—C7	0.3 (3)
C6—C5—C3—O3	−116.59 (16)	C3—O2—C2—C1	58.5 (2)
C10—C5—C3—O3	60.11 (19)	O2—C2—C1—O1	−171.0 (2)
C8—C9—C10—C5	−0.9 (3)	O2—C2—C1—C4	−51.6 (2)
C8—C9—C10—N1	178.63 (16)	C3—O3—C4—C1	−57.32 (19)
C6—C5—C10—C9	0.4 (2)	O1—C1—C4—O3	168.64 (14)
C3—C5—C10—C9	−176.42 (15)	C2—C1—C4—O3	51.2 (2)
C6—C5—C10—N1	−179.05 (14)	C9—C8—C7—C6	0.6 (3)
C3—C5—C10—N1	4.1 (2)	C5—C6—C7—C8	−1.1 (3)
O4—N1—C10—C9	−144.09 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O3i	0.82	2.08	2.8548 (18)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O3i	0.82	2.08	2.8548 (18)	157

Symmetry code: (i) .