1-Ethoxy-4-nitro­benzene

The title compound, C₈H₉NO₃, was synthesized from 4-nitro­phenol and ethyl iodide via the Williamson ether synthesis. The crystal structure has been determined at 100 K.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.048
• wR factor = 0.129
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1997-1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1-ethoxy-4-nitrobenzene

Crystal data

C8H9NO3	F(000) = 352
Mr = 167.16	Dx = 1.423 Mg m^−3
Monoclinic, P21/c	Melting point: 330.2 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.2796 (5) Å	Cell parameters from 6367 reflections
b = 11.7664 (8) Å	θ = 2.2–28.3°
c = 9.4285 (6) Å	µ = 0.11 mm^−1
β = 104.957 (1)°	T = 100 K
V = 780.23 (9) Å^3	Block, colorless
Z = 4	0.45 × 0.45 × 0.3 mm

Data collection

Bruker SMART APEX diffractometer	1936 independent reflections
Radiation source: sealed tube	1894 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.948, Tmax = 0.969	k = −15→15
8103 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	All H-atom parameters refined
S = 1.22	w = 1/[σ^2(Fo^2) + (0.0575P)^2 + 0.3353P] where P = (Fo^2 + 2Fc^2)/3
1936 reflections	(Δ/σ)max = 0.020
136 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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.

H atoms were allowed to refine isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.32511 (17)	0.68300 (9)	0.08392 (13)	0.0300 (3)
N1	0.23992 (16)	0.74291 (10)	−0.01917 (13)	0.0200 (3)
C1	0.25281 (17)	0.86572 (11)	−0.00128 (14)	0.0171 (3)
O2	0.14383 (16)	0.70363 (9)	−0.13557 (12)	0.0290 (3)
C2	0.36067 (18)	0.91110 (11)	0.13039 (14)	0.0178 (3)
H2A	0.422 (2)	0.8638 (16)	0.207 (2)	0.021*
O3	0.30202 (14)	1.21136 (8)	0.05688 (11)	0.0206 (2)
C3	0.37343 (18)	1.02736 (11)	0.14606 (14)	0.0178 (3)
H3A	0.448 (2)	1.0590 (15)	0.236 (2)	0.021*
C4	0.27830 (18)	1.09830 (11)	0.03104 (14)	0.0172 (3)
C5	0.16852 (19)	1.05195 (11)	−0.10042 (15)	0.0187 (3)
H5A	0.102 (2)	1.0991 (16)	−0.180 (2)	0.022*
C6	0.15703 (19)	0.93450 (11)	−0.11626 (15)	0.0187 (3)
H6A	0.085 (3)	0.9047 (16)	−0.206 (2)	0.022*
C7	0.2128 (2)	1.28831 (11)	−0.06000 (15)	0.0202 (3)
H7A	0.077 (3)	1.2750 (16)	−0.088 (2)	0.024*
H7B	0.263 (2)	1.2760 (15)	−0.144 (2)	0.024*
C8	0.2557 (2)	1.40737 (12)	−0.00176 (17)	0.0253 (3)
H8A	0.193 (3)	1.463 (2)	−0.079 (2)	0.038*
H8B	0.391 (3)	1.4193 (18)	0.032 (2)	0.038*
H8C	0.202 (3)	1.4192 (18)	0.082 (2)	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0357 (6)	0.0161 (5)	0.0320 (6)	0.0038 (4)	−0.0023 (5)	0.0027 (4)
N1	0.0201 (5)	0.0148 (5)	0.0242 (6)	0.0001 (4)	0.0041 (5)	−0.0008 (4)
C1	0.0172 (6)	0.0136 (6)	0.0210 (6)	−0.0004 (4)	0.0058 (5)	−0.0015 (5)
O2	0.0361 (6)	0.0190 (5)	0.0269 (6)	−0.0049 (4)	−0.0009 (5)	−0.0056 (4)
C2	0.0182 (6)	0.0172 (6)	0.0176 (6)	0.0017 (5)	0.0039 (5)	0.0022 (5)
O3	0.0281 (5)	0.0124 (5)	0.0191 (5)	0.0002 (4)	0.0021 (4)	−0.0003 (3)
C3	0.0188 (6)	0.0170 (6)	0.0163 (6)	−0.0003 (5)	0.0021 (5)	−0.0012 (5)
C4	0.0187 (6)	0.0143 (6)	0.0193 (6)	−0.0001 (4)	0.0063 (5)	−0.0003 (5)
C5	0.0191 (6)	0.0172 (6)	0.0189 (6)	0.0009 (5)	0.0032 (5)	0.0008 (5)
C6	0.0185 (6)	0.0181 (6)	0.0182 (6)	−0.0018 (5)	0.0023 (5)	−0.0024 (5)
C7	0.0248 (7)	0.0156 (6)	0.0194 (6)	0.0012 (5)	0.0043 (5)	0.0024 (5)
C8	0.0351 (8)	0.0161 (6)	0.0246 (7)	0.0007 (5)	0.0077 (6)	0.0005 (5)

Geometric parameters (Å, º)

O1—N1	1.2309 (16)	C4—C5	1.4004 (18)
N1—O2	1.2292 (15)	C5—C6	1.3901 (19)
N1—C1	1.4551 (17)	C5—H5A	0.956 (18)
C1—C6	1.3879 (18)	C6—H6A	0.942 (19)
C1—C2	1.3928 (18)	C7—C8	1.508 (2)
C2—C3	1.3764 (18)	C7—H7A	0.966 (18)
C2—H2A	0.929 (19)	C7—H7B	0.961 (18)
O3—C4	1.3554 (16)	C8—H8A	1.00 (2)
O3—C7	1.4446 (16)	C8—H8B	0.97 (2)
C3—C4	1.4018 (18)	C8—H8C	0.97 (2)
C3—H3A	0.955 (18)
O2—N1—O1	122.98 (12)	C6—C5—H5A	119.3 (11)
O2—N1—C1	118.79 (11)	C4—C5—H5A	121.6 (11)
O1—N1—C1	118.22 (11)	C1—C6—C5	119.45 (12)
C6—C1—C2	121.78 (12)	C1—C6—H6A	122.4 (11)
C6—C1—N1	118.96 (11)	C5—C6—H6A	118.1 (11)
C2—C1—N1	119.26 (11)	O3—C7—C8	107.12 (11)
C3—C2—C1	118.92 (12)	O3—C7—H7A	109.5 (11)
C3—C2—H2A	120.5 (11)	C8—C7—H7A	110.6 (11)
C1—C2—H2A	120.6 (11)	O3—C7—H7B	109.9 (11)
C4—O3—C7	117.81 (10)	C8—C7—H7B	110.6 (11)
C2—C3—C4	120.18 (12)	H7A—C7—H7B	109.2 (15)
C2—C3—H3A	119.3 (11)	C7—C8—H8A	109.1 (13)
C4—C3—H3A	120.5 (11)	C7—C8—H8B	110.7 (13)
O3—C4—C5	123.95 (12)	H8A—C8—H8B	112.7 (17)
O3—C4—C3	115.52 (11)	C7—C8—H8C	109.8 (12)
C5—C4—C3	120.52 (12)	H8A—C8—H8C	107.1 (17)
C6—C5—C4	119.15 (12)	H8B—C8—H8C	107.4 (18)
O2—N1—C1—C6	−0.27 (18)	C2—C3—C4—O3	−179.19 (11)
O1—N1—C1—C6	−179.76 (12)	C2—C3—C4—C5	0.4 (2)
O2—N1—C1—C2	179.74 (12)	O3—C4—C5—C6	178.71 (12)
O1—N1—C1—C2	0.25 (18)	C3—C4—C5—C6	−0.8 (2)
C6—C1—C2—C3	−0.50 (19)	C2—C1—C6—C5	0.1 (2)
N1—C1—C2—C3	179.49 (11)	N1—C1—C6—C5	−179.93 (12)
C1—C2—C3—C4	0.27 (19)	C4—C5—C6—C1	0.6 (2)
C7—O3—C4—C5	−1.79 (19)	C4—O3—C7—C8	178.26 (11)
C7—O3—C4—C3	177.78 (11)