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

Li, M.; Chen, X.

doi:10.1107/S1600536808036015

organic compounds

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Volume 64| Part 12| December 2008| Page o2291

doi:10.1107/S1600536808036015

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

Mei Li ^a ^* and Xin Chen ^a

^aCollege of Sciences, Tianjin University of Science and Technology, Tianjin 300457, People's Republic of China
^*Correspondence e-mail: li_mei999@163.com

(Received 29 October 2008; accepted 3 November 2008; online 8 November 2008)

In the title compound, C₁₅H₁₃NO₅, the vanillin group makes a dihedral angle of 4.95 (8)° with the benzene ring of the nitrobenzene group. The packing is stabilized by weak, non-classical intermolecular C—H⋯O interactions which link molecules into chains running along the c axis.

Related literature

For general background on Schiff bases, see: Kahwa et al. (1986 ); Santos et al. (2001 ). For bond-length data, see: Allen et al. (1987 );

Experimental

Crystal data

C₁₅H₁₃NO₅
M_r = 287.26
Orthorhombic, P b c a
a = 13.743 (3) Å
b = 12.526 (3) Å
c = 16.384 (3) Å
V = 2820.4 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 (2) K
0.23 × 0.18 × 0.12 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
15172 measured reflections
2877 independent reflections
1540 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.132
S = 0.99
2877 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O5ⁱ	0.93	2.60	3.405 (3)	146
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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, 71007a. DOI: 10.1107/S1600536808036015/at2666sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036015/at2666Isup2.hkl

checkCIF report

Comment top

Schiff-base ligands have received a good deal of attention in biology and chemistry (Kahwa et al., 1986). Many Schiff base derivatives have been synthesized and employed to develop protein and enzyme mimics (Santos et al., 2001). As a part of our interest in the coordination properties of Schiff bases functioning as ligands, we investigated the title compound, (I), used as a precursor in the preparation of Schiff bases.

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The vanillin group (C1—C7/O3/O4) is essentially planar (except the methyl H atoms), with an r.m.s. deviation for fitted atoms of 0.035 (3) Å. This group makes a dihedral angle of 4.95 (8)° with the benzene ring (C10—C15) of the nitrobenzene group.

The crystal packing is stabilized by weak, non-classical intermolecular C14—H14···O5═C7 interactions that link adjacent molecules into one-dimensional chains running along the c axis (Table 1, Fig. 2).

Related literature top

For general background on Schiff bases, see: Kahwa et al. (1986); Santos et al. (2001). For bond-length data, see: Allen et al. (1987);

Experimental top

An anhydrous acetonitrile solution (100 ml) of 4-hydroxy-3-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, in 30 min., and the mixture refluxed for 24 h under 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, and then dried in a vacuum to give the pure compound in 74% yield. Pale-yellow single crystals of (I) 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 structure of (I), with displacement ellipsoids for non-H atoms drawn at the 30% probability level.
	Fig. 2. Packing diagram for (I), with H bonds drawn as dashed lines.

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

Crystal data top

C₁₅H₁₃NO₅	F(000) = 1200
M_r = 287.26	D_x = 1.353 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3156 reflections
a = 13.743 (3) Å	θ = 2.2–26.5°
b = 12.526 (3) Å	µ = 0.10 mm⁻¹
c = 16.384 (3) Å	T = 294 K
V = 2820.4 (10) Å³	Block, pale-yellow
Z = 8	0.23 × 0.18 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2877 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
T_min = 0.932, T_max = 0.988	k = −14→15
15172 measured reflections	l = −20→18

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0424P)² + 1.1393P] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
2877 reflections	Δρ_max = 0.16 e Å⁻³
192 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (5)

Crystal data top

C₁₅H₁₃NO₅	V = 2820.4 (10) Å³
M_r = 287.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.743 (3) Å	µ = 0.10 mm⁻¹
b = 12.526 (3) Å	T = 294 K
c = 16.384 (3) Å	0.23 × 0.18 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2877 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1540 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.988	R_int = 0.045
15172 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 0.99	Δρ_max = 0.16 e Å⁻³
2877 reflections	Δρ_min = −0.17 e Å⁻³
192 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 > 2σ(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	0.14273 (18)	−0.3678 (2)	1.20564 (17)	0.0880 (7)
O1	0.1166 (2)	−0.34357 (19)	1.27401 (14)	0.1320 (9)
O2	0.1674 (2)	−0.45767 (19)	1.18670 (15)	0.1303 (9)
O3	0.11868 (11)	0.05467 (12)	0.99132 (8)	0.0671 (5)
O4	0.07376 (11)	0.23118 (12)	1.05892 (9)	0.0705 (5)
O5	0.1082 (2)	0.5139 (2)	0.82786 (17)	0.1500 (12)
C1	0.09685 (14)	0.23830 (18)	0.97787 (13)	0.0570 (5)
C2	0.09799 (15)	0.33013 (19)	0.93261 (15)	0.0671 (6)
H2	0.0826	0.3950	0.9570	0.081*
C3	0.12223 (16)	0.3267 (2)	0.84953 (16)	0.0739 (7)
C4	0.14582 (18)	0.2313 (2)	0.81422 (15)	0.0772 (7)
H4	0.1626	0.2294	0.7592	0.093*
C5	0.14517 (17)	0.1375 (2)	0.85877 (14)	0.0704 (7)
H5	0.1610	0.0730	0.8340	0.085*
C6	0.12076 (15)	0.14069 (17)	0.94062 (13)	0.0572 (6)
C7	0.1230 (2)	0.4259 (3)	0.8018 (2)	0.1087 (12)
H7	0.1361	0.4199	0.7463	0.130*
C8	0.0516 (2)	0.3282 (2)	1.10024 (16)	0.0976 (10)
H8A	0.1071	0.3747	1.0985	0.146*
H8B	0.0354	0.3130	1.1560	0.146*
H8C	−0.0027	0.3623	1.0741	0.146*
C9	0.14047 (18)	−0.04690 (17)	0.95782 (13)	0.0680 (6)
H9A	0.2033	−0.0447	0.9309	0.082*
H9B	0.0917	−0.0660	0.9176	0.082*
C10	0.14211 (15)	−0.12841 (17)	1.02476 (13)	0.0562 (5)
C11	0.16208 (16)	−0.23375 (19)	1.00431 (14)	0.0665 (6)
H11	0.1746	−0.2516	0.9502	0.080*
C12	0.16355 (17)	−0.31198 (19)	1.06322 (16)	0.0707 (7)
H12	0.1777	−0.3824	1.0496	0.085*
C13	0.14380 (16)	−0.28411 (19)	1.14254 (15)	0.0637 (6)
C14	0.12433 (18)	−0.18140 (19)	1.16476 (14)	0.0709 (7)
H14	0.1117	−0.1644	1.2190	0.085*
C15	0.12358 (17)	−0.10322 (19)	1.10550 (14)	0.0668 (6)
H15	0.1105	−0.0329	1.1200	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0997 (17)	0.0762 (17)	0.0882 (18)	−0.0093 (13)	−0.0130 (14)	0.0156 (14)
O1	0.212 (3)	0.1117 (17)	0.0727 (14)	−0.0042 (16)	0.0010 (16)	0.0221 (13)
O2	0.177 (2)	0.0729 (15)	0.141 (2)	0.0080 (15)	0.0028 (17)	0.0271 (14)
O3	0.0910 (12)	0.0563 (10)	0.0541 (9)	0.0010 (8)	0.0058 (8)	−0.0018 (7)
O4	0.0939 (12)	0.0657 (10)	0.0520 (9)	0.0107 (8)	0.0013 (8)	−0.0026 (8)
O5	0.175 (3)	0.1065 (19)	0.169 (2)	0.0499 (18)	0.0663 (19)	0.0703 (18)
C1	0.0525 (12)	0.0661 (15)	0.0524 (12)	−0.0001 (10)	−0.0015 (10)	0.0039 (11)
C2	0.0595 (14)	0.0662 (15)	0.0757 (16)	0.0055 (11)	0.0020 (12)	0.0117 (12)
C3	0.0561 (14)	0.0888 (19)	0.0768 (17)	0.0040 (13)	0.0062 (12)	0.0297 (15)
C4	0.0726 (16)	0.104 (2)	0.0555 (14)	−0.0001 (15)	0.0069 (12)	0.0140 (15)
C5	0.0762 (16)	0.0778 (17)	0.0573 (14)	−0.0025 (13)	0.0029 (12)	−0.0004 (13)
C6	0.0584 (13)	0.0597 (14)	0.0536 (13)	−0.0043 (10)	−0.0026 (10)	0.0043 (11)
C7	0.090 (2)	0.122 (3)	0.114 (2)	0.029 (2)	0.0266 (18)	0.057 (2)
C8	0.148 (3)	0.0751 (19)	0.0700 (16)	0.0201 (18)	−0.0029 (17)	−0.0147 (14)
C9	0.0865 (17)	0.0611 (15)	0.0563 (13)	0.0032 (12)	0.0080 (12)	−0.0068 (11)
C10	0.0538 (12)	0.0587 (14)	0.0562 (13)	−0.0018 (10)	0.0038 (10)	−0.0046 (10)
C11	0.0712 (15)	0.0645 (16)	0.0640 (14)	0.0029 (12)	0.0158 (11)	−0.0088 (12)
C12	0.0698 (15)	0.0577 (15)	0.0847 (18)	0.0049 (11)	0.0114 (13)	−0.0043 (13)
C13	0.0598 (13)	0.0628 (15)	0.0685 (15)	−0.0028 (11)	−0.0047 (12)	0.0070 (12)
C14	0.0905 (18)	0.0715 (17)	0.0509 (13)	−0.0038 (13)	−0.0053 (12)	−0.0051 (12)
C15	0.0865 (17)	0.0584 (14)	0.0555 (14)	−0.0008 (12)	−0.0029 (12)	−0.0085 (11)

Geometric parameters (Å, º) top

N1—O1	1.215 (3)	C7—H7	0.9300
N1—O2	1.216 (3)	C8—H8A	0.9600
N1—C13	1.472 (3)	C8—H8B	0.9600
O3—C6	1.361 (2)	C8—H8C	0.9600
O3—C9	1.418 (2)	C9—C10	1.499 (3)
O4—C1	1.368 (2)	C9—H9A	0.9700
O4—C8	1.424 (3)	C9—H9B	0.9700
O5—C7	1.199 (4)	C10—C15	1.384 (3)
C1—C2	1.369 (3)	C10—C11	1.389 (3)
C1—C6	1.406 (3)	C11—C12	1.376 (3)
C2—C3	1.402 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.373 (3)
C3—C4	1.367 (3)	C12—H12	0.9300
C3—C7	1.468 (4)	C13—C14	1.364 (3)
C4—C5	1.383 (3)	C14—C15	1.379 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.383 (3)	C15—H15	0.9300
C5—H5	0.9300

O1—N1—O2	123.3 (3)	H8A—C8—H8B	109.5
O1—N1—C13	118.2 (3)	O4—C8—H8C	109.5
O2—N1—C13	118.5 (3)	H8A—C8—H8C	109.5
C6—O3—C9	118.02 (16)	H8B—C8—H8C	109.5
C1—O4—C8	117.09 (18)	O3—C9—C10	109.34 (17)
O4—C1—C2	125.7 (2)	O3—C9—H9A	109.8
O4—C1—C6	114.77 (19)	C10—C9—H9A	109.8
C2—C1—C6	119.5 (2)	O3—C9—H9B	109.8
C1—C2—C3	120.2 (2)	C10—C9—H9B	109.8
C1—C2—H2	119.9	H9A—C9—H9B	108.3
C3—C2—H2	119.9	C15—C10—C11	118.9 (2)
C4—C3—C2	119.6 (2)	C15—C10—C9	122.8 (2)
C4—C3—C7	120.9 (3)	C11—C10—C9	118.28 (19)
C2—C3—C7	119.5 (3)	C12—C11—C10	120.7 (2)
C3—C4—C5	121.2 (2)	C12—C11—H11	119.6
C3—C4—H4	119.4	C10—C11—H11	119.6
C5—C4—H4	119.4	C13—C12—C11	118.7 (2)
C4—C5—C6	119.3 (2)	C13—C12—H12	120.7
C4—C5—H5	120.4	C11—C12—H12	120.7
C6—C5—H5	120.4	C14—C13—C12	122.1 (2)
O3—C6—C5	125.1 (2)	C14—C13—N1	118.8 (2)
O3—C6—C1	114.76 (19)	C12—C13—N1	119.1 (2)
C5—C6—C1	120.2 (2)	C13—C14—C15	118.9 (2)
O5—C7—C3	126.0 (3)	C13—C14—H14	120.5
O5—C7—H7	117.0	C15—C14—H14	120.5
C3—C7—H7	117.0	C14—C15—C10	120.7 (2)
O4—C8—H8A	109.5	C14—C15—H15	119.7
O4—C8—H8B	109.5	C10—C15—H15	119.7

C8—O4—C1—C2	−1.8 (3)	C2—C3—C7—O5	3.3 (5)
C8—O4—C1—C6	178.3 (2)	C6—O3—C9—C10	175.41 (18)
O4—C1—C2—C3	−179.5 (2)	O3—C9—C10—C15	0.6 (3)
C6—C1—C2—C3	0.4 (3)	O3—C9—C10—C11	179.86 (19)
C1—C2—C3—C4	−0.8 (3)	C15—C10—C11—C12	−0.1 (3)
C1—C2—C3—C7	179.9 (2)	C9—C10—C11—C12	−179.4 (2)
C2—C3—C4—C5	0.7 (4)	C10—C11—C12—C13	0.7 (3)
C7—C3—C4—C5	−179.9 (2)	C11—C12—C13—C14	−1.0 (4)
C3—C4—C5—C6	−0.4 (4)	C11—C12—C13—N1	178.4 (2)
C9—O3—C6—C5	−1.8 (3)	O1—N1—C13—C14	6.0 (4)
C9—O3—C6—C1	179.01 (19)	O2—N1—C13—C14	−174.4 (2)
C4—C5—C6—O3	−179.1 (2)	O1—N1—C13—C12	−173.5 (3)
C4—C5—C6—C1	0.0 (3)	O2—N1—C13—C12	6.1 (4)
O4—C1—C6—O3	−1.0 (3)	C12—C13—C14—C15	0.6 (4)
C2—C1—C6—O3	179.12 (19)	N1—C13—C14—C15	−178.8 (2)
O4—C1—C6—C5	179.83 (19)	C13—C14—C15—C10	0.1 (4)
C2—C1—C6—C5	−0.1 (3)	C11—C10—C15—C14	−0.4 (3)
C4—C3—C7—O5	−176.1 (3)	C9—C10—C15—C14	178.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O5ⁱ	0.93	2.60	3.405 (3)	146

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₅
M_r	287.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	294
a, b, c (Å)	13.743 (3), 12.526 (3), 16.384 (3)
V (Å³)	2820.4 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.18 × 0.12

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	15172, 2877, 1540
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.132, 0.99
No. of reflections	2877
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

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
C14—H14···O5ⁱ	0.93	2.60	3.405 (3)	146

Symmetry code: (i) x, −y+1/2, z+1/2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1999). SMART and SAINT for Windows NT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kahwa, I. A., Selbin, J., Hsieh, T. C.-Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185. CrossRef CAS Web of Science Google Scholar
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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doi:10.1107/S1600536808036015

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