Ethyl 2-(4-nitro-phen-oxy)acetate.

In the title mol-ecule, C(10)H(11)NO(5), the methyl C atom deviates by 0.830 (6) Å from the mean plane of the remaining non-H atoms. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the bc plane.

Related literature

For the structure of tert-butyl 2-(4-nitro­phen­oxy)acetate, see: Ali et al. (2011 ▶). For general background to ferroelectric organics, see: Fu et al. (2009 ▶); Ye et al. (2006 ▶).

Experimental

Crystal data

C10H11NO5

M = 225.20

Monoclinic,

a = 5.3848 (11) Å

b = 8.4482 (17) Å

c = 24.238 (5) Å

β = 92.59 (3)°

V = 1101.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.3 × 0.3 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.968, T max = 0.978

9279 measured reflections

2169 independent reflections

1157 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.156

S = 1.01

2169 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017242/cv5259sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017242/cv5259Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017242/cv5259Isup3.cml

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

C10H11NO5	F(000) = 472
Mr = 225.20	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3450 reflections
a = 5.3848 (11) Å	θ = 3.4–26.0°
b = 8.4482 (17) Å	µ = 0.11 mm−1
c = 24.238 (5) Å	T = 293 K
β = 92.59 (3)°	Block, colourless
V = 1101.5 (4) Å3	0.3 × 0.3 × 0.2 mm
Z = 4

Rigaku Mercury CCD diffractometer	2169 independent reflections
Radiation source: fine-focus sealed tube	1157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.089
ω scans	θmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −6→6
Tmin = 0.968, Tmax = 0.978	k = −10→10
9279 measured reflections	l = −29→29

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)] = 0.068	H-atom parameters constrained
wR(F2) = 0.156	w = 1/[σ2(Fo2) + (0.05P)2 + 0.35P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2169 reflections	Δρmax = 0.20 e Å−3
146 parameters	Δρmin = −0.21 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: 0.011 (2)

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	0.2402 (3)	0.9062 (2)	0.43476 (7)	0.0593 (5)
C4	0.3764 (4)	0.8226 (3)	0.47348 (10)	0.0502 (6)
C3	0.2863 (5)	0.8248 (3)	0.52630 (10)	0.0559 (7)
H3A	0.1438	0.8824	0.5331	0.067*
C1	0.6184 (5)	0.6596 (3)	0.55727 (11)	0.0540 (7)
C7	0.3224 (5)	0.9043 (3)	0.38008 (10)	0.0598 (7)
H7A	0.3228	0.7968	0.3661	0.072*
H7B	0.4902	0.9458	0.3794	0.072*
C6	0.7118 (5)	0.6582 (3)	0.50557 (11)	0.0600 (7)
H6A	0.8565	0.6024	0.4992	0.072*
O5	0.2362 (4)	1.0156 (3)	0.29508 (8)	0.0930 (8)
C5	0.5909 (4)	0.7396 (3)	0.46316 (11)	0.0568 (7)
H5A	0.6527	0.7389	0.4279	0.068*
N1	0.7460 (5)	0.5687 (3)	0.60109 (11)	0.0713 (7)
C2	0.4062 (5)	0.7424 (3)	0.56848 (11)	0.0588 (7)
H2A	0.3454	0.7424	0.6038	0.071*
O1	0.6650 (5)	0.5737 (3)	0.64727 (10)	0.1141 (10)
O2	0.9260 (4)	0.4885 (3)	0.59049 (9)	0.0938 (8)
C8	0.1488 (5)	1.0048 (4)	0.34495 (11)	0.0640 (8)
O4	−0.0361 (4)	1.0635 (3)	0.35870 (9)	0.1103 (10)
C9	0.0983 (7)	1.1139 (6)	0.25442 (15)	0.1140 (14)
H9A	−0.0259	1.0504	0.2344	0.137*
H9B	0.0140	1.1987	0.2730	0.137*
C10	0.2659 (8)	1.1779 (7)	0.21723 (18)	0.157 (2)
H10A	0.1762	1.2415	0.1902	0.235*
H10B	0.3491	1.0935	0.1991	0.235*
H10C	0.3863	1.2424	0.2371	0.235*

	U11	U22	U33	U12	U13	U23
O3	0.0581 (11)	0.0663 (12)	0.0541 (11)	0.0116 (9)	0.0075 (8)	0.0024 (9)
C4	0.0496 (15)	0.0462 (15)	0.0547 (15)	−0.0030 (12)	0.0012 (12)	−0.0033 (13)
C3	0.0522 (15)	0.0567 (17)	0.0594 (16)	−0.0004 (13)	0.0083 (12)	−0.0025 (14)
C1	0.0535 (16)	0.0467 (15)	0.0612 (17)	−0.0028 (13)	−0.0046 (13)	0.0025 (14)
C7	0.0612 (16)	0.0655 (18)	0.0534 (16)	0.0049 (14)	0.0104 (13)	0.0001 (14)
C6	0.0551 (16)	0.0554 (17)	0.0694 (18)	0.0060 (13)	0.0020 (14)	−0.0043 (16)
O5	0.0837 (14)	0.130 (2)	0.0668 (13)	0.0279 (14)	0.0152 (11)	0.0294 (14)
C5	0.0539 (16)	0.0596 (17)	0.0574 (15)	0.0025 (13)	0.0079 (12)	−0.0056 (14)
N1	0.0725 (17)	0.0681 (17)	0.0725 (18)	−0.0037 (14)	−0.0054 (14)	0.0084 (15)
C2	0.0636 (17)	0.0562 (17)	0.0568 (16)	−0.0076 (14)	0.0050 (13)	0.0006 (14)
O1	0.1161 (19)	0.153 (3)	0.0734 (16)	0.0334 (17)	0.0087 (14)	0.0313 (17)
O2	0.0892 (16)	0.0956 (17)	0.0954 (17)	0.0293 (14)	−0.0086 (13)	0.0132 (14)
C8	0.0609 (17)	0.076 (2)	0.0554 (16)	0.0006 (16)	0.0055 (14)	0.0000 (15)
O4	0.0937 (17)	0.161 (3)	0.0771 (15)	0.0615 (17)	0.0125 (13)	0.0127 (15)
C9	0.101 (3)	0.160 (4)	0.080 (2)	0.023 (3)	−0.002 (2)	0.043 (3)
C10	0.149 (4)	0.196 (5)	0.129 (4)	0.053 (4)	0.043 (3)	0.081 (4)

O3—C4	1.362 (3)	O5—C8	1.320 (3)
O3—C7	1.416 (3)	O5—C9	1.465 (4)
C4—C5	1.384 (3)	C5—H5A	0.9300
C4—C3	1.390 (3)	N1—O2	1.220 (3)
C3—C2	1.374 (3)	N1—O1	1.220 (3)
C3—H3A	0.9300	C2—H2A	0.9300
C1—C6	1.371 (3)	C8—O4	1.174 (3)
C1—C2	1.377 (3)	C9—C10	1.412 (5)
C1—N1	1.458 (3)	C9—H9A	0.9700
C7—C8	1.499 (4)	C9—H9B	0.9700
C7—H7A	0.9700	C10—H10A	0.9600
C7—H7B	0.9700	C10—H10B	0.9600
C6—C5	1.376 (3)	C10—H10C	0.9600
C6—H6A	0.9300
C4—O3—C7	117.25 (19)	C4—C5—H5A	120.4
O3—C4—C5	124.5 (2)	O2—N1—O1	122.2 (3)
O3—C4—C3	115.4 (2)	O2—N1—C1	119.5 (3)
C5—C4—C3	120.1 (2)	O1—N1—C1	118.3 (3)
C2—C3—C4	120.5 (2)	C3—C2—C1	118.5 (2)
C2—C3—H3A	119.8	C3—C2—H2A	120.8
C4—C3—H3A	119.8	C1—C2—H2A	120.8
C6—C1—C2	121.8 (2)	O4—C8—O5	125.0 (3)
C6—C1—N1	118.8 (2)	O4—C8—C7	126.4 (3)
C2—C1—N1	119.5 (2)	O5—C8—C7	108.7 (2)
O3—C7—C8	108.2 (2)	C10—C9—O5	109.1 (3)
O3—C7—H7A	110.1	C10—C9—H9A	109.9
C8—C7—H7A	110.1	O5—C9—H9A	109.9
O3—C7—H7B	110.1	C10—C9—H9B	109.9
C8—C7—H7B	110.1	O5—C9—H9B	109.9
H7A—C7—H7B	108.4	H9A—C9—H9B	108.3
C1—C6—C5	119.8 (2)	C9—C10—H10A	109.5
C1—C6—H6A	120.1	C9—C10—H10B	109.5
C5—C6—H6A	120.1	H10A—C10—H10B	109.5
C8—O5—C9	117.7 (3)	C9—C10—H10C	109.5
C6—C5—C4	119.3 (2)	H10A—C10—H10C	109.5
C6—C5—H5A	120.4	H10B—C10—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4i	0.93	2.53	3.177 (4)	127
C10—H10B···O1ii	0.96	2.58	3.513 (6)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.93	2.53	3.177 (4)	127
C10—H10B⋯O1ii	0.96	2.58	3.513 (6)	164

Symmetry codes: (i) ; (ii) .