1-(2-Methoxy-ethoxy)-4-nitro-benzene.

The title compound, C(9)H(11)NO(4), is an inter-mediate for dyes and drugs. The O-C-C-O chain adopts a synclinal conformation. The crystal structure is stabilized by C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Guo et al. (2006 ▶); Higson (1992 ▶).

Experimental

Crystal data

C9H11NO4

M = 197.19

Orthorhombic,

a = 11.280 (3) Å

b = 20.430 (5) Å

c = 4.1079 (10) Å

V = 946.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 (2) K

0.49 × 0.43 × 0.38 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.948, T max = 0.959

4034 measured reflections

1023 independent reflections

982 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.05

1023 reflections

130 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

Absolute structure: Flack (1983 ▶)

Flack parameter: 2 (1)

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2001 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061636/bt2633sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061636/bt2633Isup2.hkl

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

C9H11NO4	Dx = 1.384 Mg m−3
Mr = 197.19	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 2528 reflections
a = 11.280 (3) Å	θ = 2.7–27.8º
b = 20.430 (5) Å	µ = 0.11 mm−1
c = 4.1079 (10) Å	T = 100 (2) K
V = 946.7 (4) Å3	Block, colourless
Z = 4	0.49 × 0.43 × 0.38 mm
F000 = 416

Bruker SMART CCD area-detector diffractometer	1023 independent reflections
Radiation source: fine-focus sealed tube	982 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 100(2) K	θmax = 25.7º
phi and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −12→13
Tmin = 0.948, Tmax = 0.959	k = −15→24
4034 measured reflections	l = −4→4

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.1764P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.13 e Å−3
1023 reflections	Δρmin = −0.12 e Å−3
130 parameters	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.032 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Flack parameter: 2 (1)

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	−0.05088 (16)	0.68859 (9)	−0.1216 (7)	0.0407 (5)
C2	−0.08278 (16)	0.62314 (9)	−0.1160 (6)	0.0373 (5)
H2	−0.1522	0.6090	−0.2160	0.045*
C3	−0.00976 (16)	0.57971 (9)	0.0401 (6)	0.0341 (5)
H3	−0.0303	0.5357	0.0490	0.041*
C4	0.09501 (15)	0.60085 (8)	0.1858 (6)	0.0310 (5)
C5	0.12605 (16)	0.66669 (9)	0.1780 (6)	0.0382 (5)
H5	0.1956	0.6811	0.2762	0.046*
C6	0.05189 (18)	0.71044 (9)	0.0221 (7)	0.0446 (6)
H6	0.0715	0.7546	0.0143	0.054*
C7	0.27095 (16)	0.57084 (10)	0.4767 (6)	0.0363 (5)
H7A	0.2588	0.6054	0.6354	0.044*
H7B	0.3259	0.5866	0.3127	0.044*
C8	0.31983 (17)	0.51107 (10)	0.6395 (6)	0.0411 (5)
H8A	0.3888	0.5228	0.7677	0.049*
H8B	0.2608	0.4928	0.7851	0.049*
C9	0.3945 (2)	0.40593 (11)	0.5514 (9)	0.0536 (7)
H9A	0.4592	0.4164	0.6939	0.080*
H9B	0.4212	0.3762	0.3858	0.080*
H9C	0.3319	0.3858	0.6744	0.080*
N1	−0.12710 (18)	0.73499 (9)	−0.2931 (7)	0.0580 (6)
O1	−0.21750 (15)	0.71456 (9)	−0.4228 (6)	0.0687 (6)
O2	−0.09783 (16)	0.79250 (8)	−0.3004 (9)	0.0948 (10)
O3	0.16033 (10)	0.55315 (6)	0.3289 (4)	0.0354 (4)
O4	0.35171 (11)	0.46405 (7)	0.4039 (4)	0.0414 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0379 (10)	0.0363 (10)	0.0479 (14)	0.0084 (8)	0.0100 (11)	0.0041 (11)
C2	0.0314 (8)	0.0389 (10)	0.0418 (12)	0.0007 (7)	0.0028 (10)	−0.0049 (11)
C3	0.0333 (9)	0.0295 (8)	0.0396 (11)	−0.0048 (7)	0.0042 (9)	−0.0033 (10)
C4	0.0296 (9)	0.0298 (9)	0.0336 (11)	−0.0002 (7)	0.0077 (8)	−0.0041 (9)
C5	0.0335 (9)	0.0320 (9)	0.0490 (14)	−0.0071 (7)	0.0042 (10)	−0.0042 (11)
C6	0.0444 (11)	0.0268 (9)	0.0626 (16)	−0.0005 (8)	0.0092 (12)	0.0013 (11)
C7	0.0317 (9)	0.0415 (10)	0.0357 (13)	−0.0061 (8)	0.0023 (9)	−0.0074 (9)
C8	0.0382 (10)	0.0512 (12)	0.0338 (12)	−0.0022 (9)	−0.0032 (10)	−0.0010 (11)
C9	0.0465 (11)	0.0506 (12)	0.0637 (17)	0.0076 (9)	−0.0042 (13)	0.0163 (14)
N1	0.0531 (11)	0.0456 (11)	0.0752 (18)	0.0149 (9)	0.0053 (12)	0.0099 (13)
O1	0.0553 (10)	0.0677 (11)	0.0830 (15)	0.0171 (8)	−0.0121 (12)	0.0117 (13)
O2	0.0856 (13)	0.0423 (9)	0.157 (3)	0.0116 (8)	−0.0187 (18)	0.0259 (15)
O3	0.0298 (6)	0.0289 (6)	0.0474 (10)	−0.0041 (5)	−0.0013 (7)	0.0000 (7)
O4	0.0450 (7)	0.0415 (7)	0.0376 (8)	0.0067 (6)	−0.0007 (8)	0.0043 (7)

C1—C6	1.375 (3)	C7—C8	1.497 (3)
C1—C2	1.385 (3)	C7—H7A	0.9700
C1—N1	1.461 (3)	C7—H7B	0.9700
C2—C3	1.370 (3)	C8—O4	1.410 (3)
C2—H2	0.9300	C8—H8A	0.9700
C3—C4	1.393 (3)	C8—H8B	0.9700
C3—H3	0.9300	C9—O4	1.418 (3)
C4—O3	1.356 (2)	C9—H9A	0.9600
C4—C5	1.390 (2)	C9—H9B	0.9600
C5—C6	1.382 (3)	C9—H9C	0.9600
C5—H5	0.9300	N1—O2	1.221 (2)
C6—H6	0.9300	N1—O1	1.224 (3)
C7—O3	1.434 (2)
C6—C1—C2	121.69 (19)	O3—C7—H7B	110.2
C6—C1—N1	119.50 (18)	C8—C7—H7B	110.2
C2—C1—N1	118.8 (2)	H7A—C7—H7B	108.5
C3—C2—C1	118.48 (19)	O4—C8—C7	110.1 (2)
C3—C2—H2	120.8	O4—C8—H8A	109.6
C1—C2—H2	120.8	C7—C8—H8A	109.6
C2—C3—C4	120.68 (17)	O4—C8—H8B	109.6
C2—C3—H3	119.7	C7—C8—H8B	109.6
C4—C3—H3	119.7	H8A—C8—H8B	108.2
O3—C4—C5	124.65 (18)	O4—C9—H9A	109.5
O3—C4—C3	115.11 (15)	O4—C9—H9B	109.5
C5—C4—C3	120.25 (19)	H9A—C9—H9B	109.5
C6—C5—C4	118.95 (19)	O4—C9—H9C	109.5
C6—C5—H5	120.5	H9A—C9—H9C	109.5
C4—C5—H5	120.5	H9B—C9—H9C	109.5
C1—C6—C5	119.96 (18)	O2—N1—O1	122.9 (2)
C1—C6—H6	120.0	O2—N1—C1	118.5 (2)
C5—C6—H6	120.0	O1—N1—C1	118.61 (18)
O3—C7—C8	107.69 (15)	C4—O3—C7	118.38 (14)
O3—C7—H7A	110.2	C8—O4—C9	111.3 (2)
C8—C7—H7A	110.2
C6—C1—C2—C3	0.6 (4)	O3—C7—C8—O4	67.3 (2)
N1—C1—C2—C3	178.8 (2)	C6—C1—N1—O2	−0.9 (4)
C1—C2—C3—C4	−0.9 (3)	C2—C1—N1—O2	−179.2 (3)
C2—C3—C4—O3	−179.2 (2)	C6—C1—N1—O1	179.2 (3)
C2—C3—C4—C5	0.8 (3)	C2—C1—N1—O1	0.9 (4)
O3—C4—C5—C6	179.6 (2)	C5—C4—O3—C7	−1.6 (3)
C3—C4—C5—C6	−0.4 (3)	C3—C4—O3—C7	178.42 (19)
C2—C1—C6—C5	−0.2 (4)	C8—C7—O3—C4	175.33 (18)
N1—C1—C6—C5	−178.4 (2)	C7—C8—O4—C9	−177.94 (16)
C4—C5—C6—C1	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.65	3.419 (3)	140
C3—H3···O3ii	0.93	2.50	3.317 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.65	3.419 (3)	140
C3—H3⋯O3ii	0.93	2.50	3.317 (2)	147

Symmetry codes: (i) ; (ii) .