Ethyl 2-(4-nitro­phen­oxy)acetate

Sun, S.-W.

doi:10.1107/S1600536812017242

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1534

doi:10.1107/S1600536812017242

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Ethyl 2-(4-nitrophenoxy)acetate

Su-Wen Sun ^a ^*

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: sunsuwen_5127@163.com

(Received 6 March 2012; accepted 18 April 2012; online 25 April 2012)

In the title molecule, C₁₀H₁₁NO₅, 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 molecules 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_r = 225.20
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.156
S = 1.01
2169 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017242/cv5259sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812017242/cv5259Isup3.cml

checkCIF report

Comment top

The title compound, (I), has been obtain during the search for new organic compounds which demonstrate ferroelectric phase changes (Fu et al., 2009; Ye et al., 2006). Though the measured dielectric constant of (I) showed no dielectric disuniformity in the range 120–385 K (mp.393–402 K), herewith we present its crystal structure.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in tert-butyl 2-(4-nitrophenoxy)acetate (Ali et al., 2011). Atom C10 deviates at 0.830 (6) Å from the mean plane of the rest non-H atoms.Weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to bc plane.

Related literature top

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 top

4-Nitro-phenol (7 g) and 1-Bromo-butan-2-one (8.5 g) were dissolved in acetone, kalium carbonicum (7.5 g) was added to the mixture. Then the mixture was heated and refluxed by mechanical stirring at 70°C. Yellow solid was filtered off. This solid was dissolved in ethanol and single crystals suitable for X-ray structure analysis were obtained by the slow evaporation of the above solution after 3 days in air.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.

Ethyl 2-(4-nitrophenoxy)acetate top

Crystal data top

C₁₀H₁₁NO₅	F(000) = 472
M_r = 225.20	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.05P)² + 0.35P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2169 reflections	Δρ_max = 0.20 e Å⁻³
146 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₁₁NO₅	V = 1101.5 (4) Å³
M_r = 225.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.3848 (11) Å	µ = 0.11 mm⁻¹
b = 8.4482 (17) Å	T = 293 K
c = 24.238 (5) Å	0.3 × 0.3 × 0.2 mm
β = 92.59 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2169 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1157 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.978	R_int = 0.089
9279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
2169 reflections	Δρ_min = −0.21 e Å⁻³
146 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, −y+2, −z+1; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁NO₅
M_r	225.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.3848 (11), 8.4482 (17), 24.238 (5)
β (°)	92.59 (3)
V (Å³)	1101.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.3 × 0.2

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.968, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	9279, 2169, 1157
R_int	0.089
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.156, 1.01
No. of reflections	2169
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	0.93	2.53	3.177 (4)	126.5
C10—H10B···O1ⁱⁱ	0.96	2.58	3.513 (6)	164.1

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, −y+3/2, z−1/2.

Acknowledgements

The author is grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

References

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