3-Methoxy-4-(4-nitro-benz-yloxy)-benzaldehyde.

In the title compound, C(15)H(13)NO(5), the vanillin group makes a dihedral angle of 4.95 (8)° with the benzene ring of the nitro-benzene group. The packing is stabilized by weak, non-classical inter-molecular C-H⋯O inter-actions which link mol-ecules 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 = 287.26

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 0.99

2877 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.17 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, 71007a. DOI: 10.1107/S1600536808036015/at2666sup1.cif

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

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

C15H13NO5	F000 = 1200
Mr = 287.26	Dx = 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 = 2.2–26.5º
b = 12.526 (3) Å	µ = 0.10 mm−1
c = 16.384 (3) Å	T = 294 (2) K
V = 2820.4 (10) Å3	Block, pale-yellow
Z = 8	0.23 × 0.18 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	2877 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 294(2) K	θmax = 26.4º
φ and ω scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −16→17
Tmin = 0.932, Tmax = 0.988	k = −14→15
15172 measured reflections	l = −20→18

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0424P)2 + 1.1393P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.132	(Δ/σ)max = 0.001
S = 0.99	Δρmax = 0.16 e Å−3
2877 reflections	Δρmin = −0.17 e Å−3
192 parameters	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)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .