4-Meth­oxy-3-nitro­biphen­yl

Chao, X.; Zhang, X.; Wang, K.; Ji, J.; Chen, Q.

doi:10.1107/S1600536811052846

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o114

doi:10.1107/S1600536811052846

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4-Methoxy-3-nitrobiphenyl

Xuqiang Chao,^a Xiuqin Zhang,^b Kai Wang,^b Jun Ji ^a and Qiang Chen ^b ^*

^aSchool of Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China, and ^bHigh Technology Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China
^*Correspondence e-mail: cxq_cczu@163.com

(Received 24 November 2011; accepted 8 December 2011; online 14 December 2011)

In the title compound, C₁₃H₁₁NO₃, the dihedral angle between the two benzene rings is 36.69 (2)° and the nitro and methyoxy groups are oriented at 29.12 (14) and 2.14 (12)° with respect to the benzene ring to which they are bonded.

Related literature

For background information and the synthetic procedure, see: Pourali & Fatemi (2010 ). For the crystal structure of a similar compound, see: Marques et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₁NO₃
M_r = 229.23
Orthorhombic, P b c a
a = 7.2464 (14) Å
b = 14.416 (3) Å
c = 21.270 (4) Å
V = 2221.9 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.981, T_max = 0.985
23696 measured reflections
2067 independent reflections
1767 reflections with I > 2σ(I)
R_int = 0.042
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.134
S = 1.00
2067 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811052846/pv2490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052846/pv2490Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052846/pv2490Isup3.cml

checkCIF report

Comment top

The tittle compound is used as an important intermediate in the synthesis of bifenazate which is recognized as an effective miticide (Pourali & Fatemi, 2010).

The bond lengths and angles in the title compound (Fig. 1) are similar to the corresponding bond lengths and angles reported for a closely related compound (Marques et al., 2008). In the title molecule, the torsion angle between the two benzene rings is 36.69 (2)° and the nitro (N1/O2/O3) and methyoxy (O1/C11) groups are oriented at 29.12 (14) and 2.14 (12)°, respectively, with respect to the benzene ring (C5–C10). The crystal structure is devoid of any intramolecular or intermolecular hydrogen bonds.

Related literature top

For background information and the synthetic procedure, see: Pourali & Fatemi (2010). For the crystal structure of a similar compound, see: Marques et al. (2008).

Experimental top

The title compound was prepared by a method reported in the literature (Pourali & Fatemi, 2010). A solution of 3-nitrobiphenyl-4-ol (2 g, 9.3 mmol) in acetone (20 ml) was added slowly to a solution of dimethyl sulfate (1.2 g, 18 mmol) in an ice bath. After stirring for 48 h at room tempeature, the solvent was evaporated on a rotary evaporator to yield the title compound. Colorless block of the title compound were grown in ethanol by slow slow evaporation of the solvent at room temperature.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule; displacement ellipsoids are drawn at the 50% probability level.

4-Methoxy-3-nitrobiphenyl top

Crystal data top

C₁₃H₁₁NO₃	F(000) = 960
M_r = 229.23	D_x = 1.371 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7392 reflections
a = 7.2464 (14) Å	θ = 2.8–28.6°
b = 14.416 (3) Å	µ = 0.10 mm⁻¹
c = 21.270 (4) Å	T = 296 K
V = 2221.9 (7) Å³	Block, colorless
Z = 8	0.20 × 0.18 × 0.15 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 25.5°, θ_min = 1.9°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −17→17
T_min = 0.981, T_max = 0.985	l = −25→13
23696 measured reflections	3 standard reflections every 200 reflections
2067 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0647P)² + 1.1253P] where P = (F_o² + 2F_c²)/3
2067 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₃H₁₁NO₃	V = 2221.9 (7) Å³
M_r = 229.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.2464 (14) Å	µ = 0.10 mm⁻¹
b = 14.416 (3) Å	T = 296 K
c = 21.270 (4) Å	0.20 × 0.18 × 0.15 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1767 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.042
T_min = 0.981, T_max = 0.985	3 standard reflections every 200 reflections
23696 measured reflections	intensity decay: 1%
2067 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
2067 reflections	Δρ_min = −0.21 e Å⁻³
155 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
O1	0.0839 (2)	0.29025 (9)	0.20268 (6)	0.0550 (4)
C6	0.0647 (2)	0.25993 (12)	0.37180 (9)	0.0440 (4)
H6	0.0437	0.2118	0.4000	0.053*
C10	0.1357 (2)	0.41652 (12)	0.35023 (9)	0.0470 (4)
H10	0.1629	0.4762	0.3640	0.056*
C5	0.1047 (2)	0.34788 (12)	0.39446 (9)	0.0429 (4)
N1	0.0116 (2)	0.14832 (10)	0.28966 (8)	0.0510 (4)
C7	0.0557 (2)	0.24306 (11)	0.30850 (9)	0.0435 (4)
C8	0.0879 (2)	0.31220 (12)	0.26371 (8)	0.0433 (4)
C9	0.1278 (3)	0.39972 (12)	0.28690 (9)	0.0469 (4)
H9	0.1496	0.4481	0.2589	0.056*
C2	0.1145 (2)	0.36642 (12)	0.46247 (9)	0.0460 (4)
O3	0.0541 (3)	0.08624 (9)	0.32547 (8)	0.0732 (5)
C11	0.1229 (3)	0.36171 (14)	0.15871 (9)	0.0558 (5)
H11A	0.0316	0.4097	0.1623	0.084*
H11B	0.1208	0.3366	0.1169	0.084*
H11C	0.2428	0.3872	0.1672	0.084*
O2	−0.0705 (3)	0.13539 (11)	0.24097 (9)	0.0828 (6)
C3	0.2432 (3)	0.42742 (15)	0.48667 (10)	0.0614 (6)
H3	0.3226	0.4583	0.4594	0.074*
C1	−0.0019 (3)	0.32329 (14)	0.50488 (10)	0.0586 (5)
H1	−0.0906	0.2820	0.4902	0.070*
C4	0.2562 (4)	0.44336 (18)	0.55029 (11)	0.0723 (6)
H4	0.3444	0.4846	0.5654	0.087*
C12	0.0112 (3)	0.34047 (17)	0.56840 (11)	0.0670 (6)
H12	−0.0698	0.3114	0.5960	0.080*
C13	0.1418 (3)	0.39961 (17)	0.59124 (11)	0.0692 (6)
H13	0.1524	0.4098	0.6343	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0698 (9)	0.0411 (7)	0.0541 (8)	−0.0008 (6)	0.0041 (7)	0.0009 (6)
C6	0.0395 (9)	0.0348 (8)	0.0578 (11)	0.0008 (7)	0.0014 (8)	0.0070 (8)
C10	0.0436 (10)	0.0329 (8)	0.0645 (11)	−0.0037 (7)	0.0048 (8)	−0.0016 (8)
C5	0.0334 (8)	0.0375 (9)	0.0578 (10)	−0.0006 (7)	0.0001 (7)	0.0015 (8)
N1	0.0559 (10)	0.0314 (8)	0.0657 (10)	−0.0010 (7)	0.0037 (8)	0.0006 (7)
C7	0.0377 (9)	0.0298 (8)	0.0628 (11)	0.0008 (7)	0.0002 (8)	0.0000 (7)
C8	0.0387 (9)	0.0344 (8)	0.0569 (11)	0.0036 (7)	0.0040 (8)	0.0029 (7)
C9	0.0465 (10)	0.0355 (9)	0.0587 (11)	−0.0009 (8)	0.0056 (8)	0.0072 (8)
C2	0.0397 (9)	0.0406 (9)	0.0577 (11)	0.0038 (7)	0.0003 (8)	0.0010 (8)
O3	0.1017 (13)	0.0329 (7)	0.0850 (11)	0.0030 (7)	0.0018 (9)	0.0080 (7)
C11	0.0595 (12)	0.0506 (11)	0.0572 (11)	0.0030 (9)	0.0050 (9)	0.0065 (9)
O2	0.1095 (15)	0.0509 (9)	0.0879 (12)	−0.0175 (9)	−0.0282 (11)	−0.0060 (8)
C3	0.0554 (12)	0.0646 (13)	0.0642 (12)	−0.0117 (10)	0.0057 (10)	−0.0110 (10)
C1	0.0580 (12)	0.0539 (11)	0.0638 (12)	−0.0048 (10)	0.0011 (10)	0.0083 (9)
C4	0.0679 (14)	0.0767 (15)	0.0722 (14)	−0.0068 (12)	−0.0060 (12)	−0.0211 (12)
C12	0.0643 (14)	0.0740 (15)	0.0628 (13)	0.0079 (12)	0.0098 (11)	0.0143 (11)
C13	0.0696 (15)	0.0787 (15)	0.0593 (13)	0.0147 (13)	−0.0017 (11)	−0.0035 (11)

Geometric parameters (Å, º) top

O1—C8	1.336 (2)	C2—C1	1.383 (3)
O1—C11	1.420 (2)	C2—C3	1.381 (3)
C6—C7	1.370 (3)	C11—H11A	0.9600
C6—C5	1.387 (2)	C11—H11B	0.9600
C6—H6	0.9300	C11—H11C	0.9600
C10—C9	1.370 (3)	C3—C4	1.376 (3)
C10—C5	1.384 (2)	C3—H3	0.9300
C10—H10	0.9300	C1—C12	1.377 (3)
C5—C2	1.473 (3)	C1—H1	0.9300
N1—O2	1.209 (2)	C4—C13	1.358 (3)
N1—O3	1.215 (2)	C4—H4	0.9300
N1—C7	1.459 (2)	C12—C13	1.363 (4)
C7—C8	1.398 (2)	C12—H12	0.9300
C8—C9	1.385 (3)	C13—H13	0.9300
C9—H9	0.9300

C8—O1—C11	117.63 (15)	C1—C2—C5	121.99 (17)
C7—C6—C5	120.92 (16)	C3—C2—C5	120.93 (17)
C7—C6—H6	119.5	O1—C11—H11A	109.5
C5—C6—H6	119.5	O1—C11—H11B	109.5
C9—C10—C5	122.37 (17)	H11A—C11—H11B	109.5
C9—C10—H10	118.8	O1—C11—H11C	109.5
C5—C10—H10	118.8	H11A—C11—H11C	109.5
C10—C5—C6	116.83 (17)	H11B—C11—H11C	109.5
C10—C5—C2	122.02 (16)	C4—C3—C2	121.3 (2)
C6—C5—C2	121.15 (16)	C4—C3—H3	119.4
O2—N1—O3	123.26 (17)	C2—C3—H3	119.4
O2—N1—C7	119.17 (16)	C12—C1—C2	121.1 (2)
O3—N1—C7	117.51 (17)	C12—C1—H1	119.4
C6—C7—C8	122.36 (16)	C2—C1—H1	119.4
C6—C7—N1	116.53 (16)	C13—C4—C3	120.8 (2)
C8—C7—N1	121.11 (17)	C13—C4—H4	119.6
O1—C8—C9	124.48 (16)	C3—C4—H4	119.6
O1—C8—C7	119.30 (16)	C13—C12—C1	120.7 (2)
C9—C8—C7	116.20 (16)	C13—C12—H12	119.7
C10—C9—C8	121.33 (16)	C1—C12—H12	119.7
C10—C9—H9	119.3	C4—C13—C12	119.1 (2)
C8—C9—H9	119.3	C4—C13—H13	120.5
C1—C2—C3	117.07 (19)	C12—C13—H13	120.5

C9—C10—C5—C6	0.0 (3)	C5—C10—C9—C8	0.0 (3)
C9—C10—C5—C2	179.66 (17)	O1—C8—C9—C10	−177.71 (17)
C7—C6—C5—C10	−0.4 (3)	C7—C8—C9—C10	0.3 (3)
C7—C6—C5—C2	179.97 (16)	C10—C5—C2—C1	144.19 (19)
C5—C6—C7—C8	0.7 (3)	C6—C5—C2—C1	−36.2 (3)
C5—C6—C7—N1	−179.67 (15)	C10—C5—C2—C3	−36.6 (3)
O2—N1—C7—C6	149.8 (2)	C6—C5—C2—C3	143.06 (19)
O3—N1—C7—C6	−27.5 (2)	C1—C2—C3—C4	0.9 (3)
O2—N1—C7—C8	−30.6 (3)	C5—C2—C3—C4	−178.4 (2)
O3—N1—C7—C8	152.12 (18)	C3—C2—C1—C12	−0.3 (3)
C11—O1—C8—C9	−0.1 (3)	C5—C2—C1—C12	178.99 (19)
C11—O1—C8—C7	−178.07 (16)	C2—C3—C4—C13	−0.3 (4)
C6—C7—C8—O1	177.44 (16)	C2—C1—C12—C13	−1.0 (3)
N1—C7—C8—O1	−2.1 (2)	C3—C4—C13—C12	−1.0 (4)
C6—C7—C8—C9	−0.7 (3)	C1—C12—C13—C4	1.6 (4)
N1—C7—C8—C9	179.73 (16)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁NO₃
M_r	229.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	7.2464 (14), 14.416 (3), 21.270 (4)
V (Å³)	2221.9 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	23696, 2067, 1767
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.134, 1.00
No. of reflections	2067
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Marques, A. T., Silva, J. A., Silva, M. R., Beja, A. M., Justino, L. L. G. & Sobral, A. J. F. N. (2008). J. Chem. Crystallogr. 38, 295–299. Web of Science CSD CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Pourali, A. R. & Fatemi, F. (2010). Chin. Chem. Lett. 21, 1283–1286. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar