4-Meth-oxy-3-(4-nitro-benz-yloxy)benzaldehyde.

In the title compound, C(15)H(13)NO(5), the two benzene rings make a dihedral angle of 3.98 (7)°. The crystal packing is stabilized by weak non-classical inter-molecular C-H⋯O inter-actions that link mol-ecules into centrosymmetric tetra-mers.

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 = 287.26

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.133

S = 1.12

3161 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016618/wn2430sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811016618/wn2430Isup3.cml

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

C15H13NO5	F(000) = 600
Mr = 287.26	Dx = 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

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

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(Fo2) + (0.0561P)2 + 0.2245P] where P = (Fo2 + 2Fc2)/3
3161 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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
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*

	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)

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

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

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) ; (ii) ; (iii) .