4-Meth­oxy-3-(4-nitro­benz­yloxy)benzaldehyde

Duan, Z.-Y.; Ma, G.-L.; Yang, L.-P.

doi:10.1107/S1600536811016618

organic compounds

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Volume 67| Part 6| June 2011| Page o1377

doi:10.1107/S1600536811016618

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4-Methoxy-3-(4-nitrobenzyloxy)benzaldehyde

Zhong-Yu Duan,^a ^* Guo-Li Ma ^a and Li-Ping Yang ^a

^aCollege of Chemical Engineering, Hebei University of Technology, Tianjin 300130, People's Republic of China
^*Correspondence e-mail: duan_zhongyu99@163.com

(Received 12 April 2011; accepted 3 May 2011; online 11 May 2011)

In the title compound, C₁₅H₁₃NO₅, the two benzene rings make a dihedral angle of 3.98 (7)°. The crystal packing is stabilized by weak non-classical intermolecular C—H⋯O interactions that link molecules into centrosymmetric tetramers.

Related literature

For general background to the use of Schiff base derivatives in the development protein and enzyme mimics, see: Santos et al. (2001 ). For a closely related crystal structure, see: Li & Chen (2008 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₃NO₅
M_r = 287.26
Monoclinic, P 2₁ /c
a = 6.853 (1) Å
b = 11.994 (2) Å
c = 16.405 (3) Å
β = 98.28 (3)°
V = 1334.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 K
0.22 × 0.16 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.932, T_max = 0.988
10078 measured reflections
3161 independent reflections
2441 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.133
S = 1.12
3161 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.26 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
C12—H12⋯O3ⁱ	0.93	2.42	3.280 (2)	154
C9—H9A⋯O5ⁱⁱ	0.97	2.53	3.383 (2)	147
C8—H8B⋯O4ⁱⁱⁱ	0.96	2.55	3.410 (3)	150
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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/S1600536811016618/wn2430sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016618/wn2430Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016618/wn2430Isup3.cml

checkCIF report

Comment top

Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). The synthesis and crystal structures of numerous derivatives have been published. In particular, the isomeric 3-methoxy-4-(4-nitrobenzyloxy)benzaldehyde crystal structure has been reported (Li & Chen, 2008). As a part of our interest in the coordination properties of Schiff bases functioning as ligands, we have investigated the title compound, which has been used as a precursor in the preparation of Schiff bases.

In the title molecule (Fig. 1), bond lengths (Allen et al., 1987) and angles are within normal ranges. The two benzene rings make a dihedral angle of 3.98 (7)° with each other. A similar value of 4.99 (6)° is observed in 3-methoxy-4-(4-nitrobenzyloxy)benzaldehyde (Li & Chen, 2008).

The crystal packing is stabilised by weak, non-classical intermolecular C12—H12···O3═C7, C8—H8B···O4 and C9—H9A···O5 interactions that link adjacent molecules into centrosymmetric tetramers (Table 1, Fig. 2).

Related literature top

For general background to the use of Schiff base derivatives in the development

protein and enzyme mimics, see: Santos et al. (2001). For a closely related crystal structure, see: Li & Chen (2008). For reference bond-length data, see: Allen et al. (1987).

Experimental top

An anhydrous acetonitrile solution (100 ml) of 3-hydroxy-4-methoxybenzaldehyde (1.52 g, 10 mmol) was added dropwise to a solution (50 ml) of 1-(bromomethyl)-4-nitrobenzene (2.16 g, 10 mmol) and pyridine (0.79 g, 10 mmol) in acetonitrile, over a period of 30 min., and the mixture refluxed for 24 h under a nitrogen atmosphere. The solvent was removed and the resultant mixture poured into ice-water (100 ml). The yellow precipitate was then isolated and recrystallized from acetonitrile. It was then dried in a vacuum to give the pure compound in 78% yield. Pale-yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. A packing diagram of the crystal structure, with H bonds drawn as dashed lines. The tetramers are indicated by red and green lines.

4-Methoxy-3-(4-nitrobenzyloxy)benzaldehyde top

Crystal data top

C₁₅H₁₃NO₅	F(000) = 600
M_r = 287.26	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3519 reflections
a = 6.853 (1) Å	θ = 2.3–26.2°
b = 11.994 (2) Å	µ = 0.11 mm⁻¹
c = 16.405 (3) Å	T = 294 K
β = 98.28 (3)°	Block, pale-yellow
V = 1334.4 (4) Å³	0.22 × 0.16 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3161 independent reflections
Radiation source: fine-focus sealed tube	2441 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 27.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.932, T_max = 0.988	k = −14→15
10078 measured reflections	l = −19→21

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0561P)² + 0.2245P] where P = (F_o² + 2F_c²)/3
3161 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₃NO₅	V = 1334.4 (4) Å³
M_r = 287.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.853 (1) Å	µ = 0.11 mm⁻¹
b = 11.994 (2) Å	T = 294 K
c = 16.405 (3) Å	0.22 × 0.16 × 0.11 mm
β = 98.28 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3161 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2441 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.988	R_int = 0.047
10078 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.12	Δρ_max = 0.26 e Å⁻³
3161 reflections	Δρ_min = −0.21 e Å⁻³
191 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
N1	0.3564 (2)	−0.20291 (14)	0.78771 (10)	0.0282 (4)
O1	0.23378 (17)	0.07084 (9)	0.45431 (7)	0.0228 (3)
O2	0.27616 (18)	0.28142 (10)	0.46497 (8)	0.0261 (3)
O3	0.1082 (2)	−0.00461 (10)	0.13474 (9)	0.0356 (4)
O4	0.3643 (2)	−0.13342 (13)	0.84335 (9)	0.0419 (4)
O5	0.3704 (2)	−0.30380 (11)	0.79970 (9)	0.0387 (4)
C1	0.1427 (2)	0.14338 (14)	0.23296 (11)	0.0216 (4)
C2	0.1670 (2)	0.07594 (14)	0.30415 (11)	0.0204 (4)
H2	0.1562	−0.0012	0.2995	0.024*
C3	0.2070 (2)	0.12507 (14)	0.38043 (11)	0.0199 (4)
C4	0.2282 (2)	0.24204 (14)	0.38720 (11)	0.0214 (4)
C5	0.2003 (3)	0.30806 (14)	0.31727 (12)	0.0241 (4)
H5A	0.2104	0.3852	0.3218	0.029*
C6	0.1573 (2)	0.25824 (14)	0.24028 (11)	0.0237 (4)
H6	0.1380	0.3024	0.1932	0.028*
C7	0.1090 (3)	0.09431 (15)	0.15046 (12)	0.0274 (4)
H7	0.0862	0.1432	0.1061	0.033*
C8	0.3346 (3)	0.39608 (15)	0.47346 (13)	0.0326 (5)
H8A	0.4333	0.4111	0.4389	0.049*
H8B	0.3874	0.4110	0.5298	0.049*
H8C	0.2221	0.4430	0.4573	0.049*
C9	0.2195 (2)	−0.04779 (13)	0.45450 (11)	0.0196 (4)
H9A	0.3148	−0.0800	0.4229	0.024*
H9B	0.0886	−0.0709	0.4298	0.024*
C10	0.2599 (2)	−0.08656 (13)	0.54244 (10)	0.0174 (3)
C11	0.2435 (2)	−0.19985 (14)	0.55914 (11)	0.0221 (4)
H11	0.2101	−0.2496	0.5159	0.027*
C12	0.2765 (2)	−0.23909 (14)	0.63929 (12)	0.0226 (4)
H12	0.2654	−0.3146	0.6505	0.027*
C13	0.3264 (2)	−0.16299 (14)	0.70222 (11)	0.0209 (4)
C14	0.3467 (2)	−0.05042 (14)	0.68780 (11)	0.0210 (4)
H14	0.3820	−0.0011	0.7312	0.025*
C15	0.3131 (2)	−0.01262 (14)	0.60716 (11)	0.0198 (4)
H15	0.3263	0.0629	0.5962	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0235 (7)	0.0388 (9)	0.0219 (9)	−0.0008 (7)	0.0020 (6)	0.0092 (7)
O1	0.0325 (7)	0.0192 (6)	0.0165 (7)	0.0005 (5)	0.0032 (5)	0.0041 (5)
O2	0.0361 (7)	0.0228 (7)	0.0194 (7)	−0.0045 (5)	0.0035 (5)	−0.0001 (5)
O3	0.0508 (9)	0.0282 (7)	0.0270 (8)	−0.0017 (6)	0.0027 (7)	−0.0002 (6)
O4	0.0527 (9)	0.0535 (9)	0.0186 (8)	0.0001 (7)	0.0021 (7)	−0.0008 (7)
O5	0.0439 (8)	0.0390 (8)	0.0325 (9)	0.0001 (6)	0.0031 (6)	0.0191 (7)
C1	0.0198 (8)	0.0251 (9)	0.0200 (9)	−0.0004 (7)	0.0036 (7)	0.0021 (7)
C2	0.0184 (8)	0.0222 (8)	0.0205 (9)	−0.0006 (6)	0.0027 (7)	0.0027 (7)
C3	0.0184 (8)	0.0226 (9)	0.0194 (9)	0.0013 (6)	0.0048 (7)	0.0059 (7)
C4	0.0190 (8)	0.0246 (9)	0.0213 (9)	−0.0002 (6)	0.0051 (7)	0.0005 (7)
C5	0.0269 (9)	0.0210 (8)	0.0247 (10)	0.0006 (7)	0.0044 (7)	0.0041 (7)
C6	0.0239 (8)	0.0253 (9)	0.0221 (10)	0.0025 (7)	0.0045 (7)	0.0081 (7)
C7	0.0303 (10)	0.0307 (10)	0.0211 (10)	0.0016 (8)	0.0037 (7)	0.0060 (8)
C8	0.0448 (11)	0.0232 (9)	0.0286 (11)	−0.0065 (8)	0.0007 (9)	−0.0028 (8)
C9	0.0209 (8)	0.0189 (8)	0.0194 (9)	0.0004 (6)	0.0039 (6)	0.0016 (7)
C10	0.0153 (7)	0.0218 (8)	0.0159 (9)	0.0011 (6)	0.0047 (6)	0.0025 (7)
C11	0.0235 (8)	0.0218 (8)	0.0212 (10)	−0.0009 (7)	0.0037 (7)	−0.0004 (7)
C12	0.0222 (8)	0.0194 (8)	0.0264 (10)	0.0004 (6)	0.0037 (7)	0.0051 (7)
C13	0.0174 (8)	0.0281 (9)	0.0173 (9)	0.0029 (7)	0.0031 (6)	0.0066 (7)
C14	0.0194 (8)	0.0245 (9)	0.0186 (9)	0.0017 (7)	0.0013 (7)	−0.0013 (7)
C15	0.0186 (8)	0.0193 (8)	0.0218 (9)	0.0010 (6)	0.0041 (7)	0.0018 (7)

Geometric parameters (Å, º) top

N1—O5	1.228 (2)	C7—H7	0.9300
N1—O4	1.232 (2)	C8—H8A	0.9600
N1—C13	1.468 (2)	C8—H8B	0.9600
O1—C3	1.365 (2)	C8—H8C	0.9600
O1—C9	1.4262 (19)	C9—C10	1.503 (2)
O2—C4	1.356 (2)	C9—H9A	0.9700
O2—C8	1.433 (2)	C9—H9B	0.9700
O3—C7	1.214 (2)	C10—C15	1.391 (2)
C1—C6	1.385 (2)	C10—C11	1.394 (2)
C1—C2	1.411 (2)	C11—C12	1.384 (2)
C1—C7	1.463 (3)	C11—H11	0.9300
C2—C3	1.374 (2)	C12—C13	1.383 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.413 (2)	C13—C14	1.381 (2)
C4—C5	1.384 (2)	C14—C15	1.386 (2)
C5—C6	1.390 (3)	C14—H14	0.9300
C5—H5A	0.9300	C15—H15	0.9300
C6—H6	0.9300

O5—N1—O4	123.67 (17)	H8A—C8—H8B	109.5
O5—N1—C13	118.13 (16)	O2—C8—H8C	109.5
O4—N1—C13	118.20 (15)	H8A—C8—H8C	109.5
C3—O1—C9	118.49 (13)	H8B—C8—H8C	109.5
C4—O2—C8	116.89 (14)	O1—C9—C10	107.92 (13)
C6—C1—C2	120.00 (16)	O1—C9—H9A	110.1
C6—C1—C7	118.69 (16)	C10—C9—H9A	110.1
C2—C1—C7	121.27 (16)	O1—C9—H9B	110.1
C3—C2—C1	119.48 (16)	C10—C9—H9B	110.1
C3—C2—H2	120.3	H9A—C9—H9B	108.4
C1—C2—H2	120.3	C15—C10—C11	119.41 (16)
O1—C3—C2	126.01 (15)	C15—C10—C9	121.81 (15)
O1—C3—C4	113.84 (15)	C11—C10—C9	118.78 (15)
C2—C3—C4	120.13 (16)	C12—C11—C10	120.76 (16)
O2—C4—C5	124.50 (16)	C12—C11—H11	119.6
O2—C4—C3	115.35 (15)	C10—C11—H11	119.6
C5—C4—C3	120.15 (17)	C13—C12—C11	118.26 (16)
C4—C5—C6	119.54 (16)	C13—C12—H12	120.9
C4—C5—H5A	120.2	C11—C12—H12	120.9
C6—C5—H5A	120.2	C14—C13—C12	122.49 (16)
C1—C6—C5	120.64 (16)	C14—C13—N1	118.61 (16)
C1—C6—H6	119.7	C12—C13—N1	118.90 (16)
C5—C6—H6	119.7	C13—C14—C15	118.45 (16)
O3—C7—C1	125.79 (17)	C13—C14—H14	120.8
O3—C7—H7	117.1	C15—C14—H14	120.8
C1—C7—H7	117.1	C14—C15—C10	120.61 (15)
O2—C8—H8A	109.5	C14—C15—H15	119.7
O2—C8—H8B	109.5	C10—C15—H15	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3ⁱ	0.93	2.42	3.280 (2)	154
C9—H9A···O5ⁱⁱ	0.97	2.53	3.383 (2)	147
C8—H8B···O4ⁱⁱⁱ	0.96	2.55	3.410 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₅
M_r	287.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	6.853 (1), 11.994 (2), 16.405 (3)
β (°)	98.28 (3)
V (Å³)	1334.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.16 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.932, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	10078, 3161, 2441
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.133, 1.12
No. of reflections	3161
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.21

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), 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
C12—H12···O3ⁱ	0.93	2.42	3.280 (2)	154
C9—H9A···O5ⁱⁱ	0.97	2.53	3.383 (2)	147
C8—H8B···O4ⁱⁱⁱ	0.96	2.55	3.410 (3)	150

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

Acknowledgements

The project was supported by Hebei Provincial Natural Science Foundation of China (project grant No. B2010000039).

References

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