(E)-2-Hydr­oxy-3-meth­oxy-5-[(3-methoxy­phen­yl)diazen­yl]benzaldehyde

The mol­ecule of the title compound, C₁₅H₁₄N₂O₄, is approximately planar and displays a trans configuration with respect to the N=N double bond. The mol­ecules are linked by inter­molecular C—H...O and C—H...π inter­actions, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.046
• wR factor = 0.078
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLUTON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-2-hydroxy-3-methoxy-5-[(3-methoxyphenyl)diazenyl]benzaldehyde

Crystal data

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.382 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8411 reflections
a = 11.8486 (14) Å	θ = 2.7–27.5°
b = 9.9295 (9) Å	µ = 0.10 mm^−1
c = 12.6574 (15) Å	T = 296 K
β = 112.441 (9)°	Plate, brown
V = 1376.4 (3) Å^3	0.36 × 0.27 × 0.11 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	1298 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.083
Plane graphite monochromator	θmax = 25.0°, θmin = 2.7°
ω scans	h = −14→14
16858 measured reflections	k = −11→11
2414 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.026P)^2] where P = (Fo^2 + 2Fc^2)/3
2414 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.13 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.56244 (19)	0.7409 (2)	0.42607 (18)	0.0425 (6)
C2	0.5815 (2)	0.7860 (2)	0.33005 (18)	0.0468 (6)
H2	0.6451	0.7517	0.3121	0.056*
C3	0.5041 (2)	0.8825 (2)	0.2624 (2)	0.0502 (6)
H3	0.5152	0.9123	0.1974	0.060*
C4	0.4103 (2)	0.9361 (2)	0.28820 (19)	0.0485 (6)
H4	0.3593	1.0015	0.2414	0.058*
C5	0.3928 (2)	0.8919 (2)	0.3839 (2)	0.0487 (6)
C6	0.4697 (2)	0.7937 (2)	0.45270 (19)	0.0504 (6)
H6	0.4580	0.7634	0.5174	0.060*
C7	0.78460 (19)	0.4862 (2)	0.55165 (19)	0.0389 (5)
C8	0.8711 (2)	0.4217 (2)	0.52223 (19)	0.0437 (6)
H8	0.8790	0.4431	0.4538	0.052*
C9	0.94728 (19)	0.3241 (2)	0.59410 (18)	0.0417 (6)
C10	0.93330 (19)	0.2916 (2)	0.69568 (18)	0.0421 (5)
C11	0.8439 (2)	0.3560 (2)	0.72472 (19)	0.0419 (5)
C12	0.7711 (2)	0.4524 (2)	0.65352 (18)	0.0418 (6)
H12	0.7122	0.4957	0.6731	0.050*
C13	1.0370 (2)	0.2555 (3)	0.5617 (2)	0.0556 (7)
H13	1.0424	0.2783	0.4925	0.067*
C14	0.7436 (2)	0.3720 (2)	0.8551 (2)	0.0585 (7)
H14A	0.7479	0.3345	0.9265	0.088*
H14B	0.6650	0.3532	0.7969	0.088*
H14C	0.7555	0.4677	0.8630	0.088*
C15	0.2246 (2)	1.0406 (3)	0.3538 (2)	0.0757 (8)
H15A	0.1670	1.0627	0.3877	0.114*
H15B	0.1817	1.0099	0.2769	0.114*
H15C	0.2717	1.1191	0.3531	0.114*
N1	0.63461 (17)	0.64051 (18)	0.50386 (15)	0.0480 (5)
N2	0.71296 (17)	0.58555 (18)	0.47381 (15)	0.0446 (5)
O1	0.83686 (14)	0.31334 (16)	0.82374 (13)	0.0584 (5)
O2	1.00397 (14)	0.19852 (16)	0.76869 (13)	0.0622 (5)
H1	1.0529	0.1679	0.7434	0.093*
O3	1.10618 (17)	0.16912 (19)	0.62071 (17)	0.0786 (6)
O4	0.30405 (16)	0.93703 (17)	0.41873 (15)	0.0711 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0424 (13)	0.0397 (14)	0.0405 (13)	0.0026 (11)	0.0104 (11)	0.0036 (11)
C2	0.0471 (14)	0.0414 (14)	0.0525 (15)	−0.0014 (12)	0.0198 (12)	−0.0005 (12)
C3	0.0583 (16)	0.0439 (15)	0.0486 (15)	−0.0019 (13)	0.0204 (14)	0.0099 (12)
C4	0.0503 (15)	0.0421 (15)	0.0473 (15)	0.0031 (11)	0.0121 (13)	0.0083 (11)
C5	0.0474 (15)	0.0464 (15)	0.0506 (15)	0.0084 (12)	0.0168 (13)	0.0040 (13)
C6	0.0571 (16)	0.0508 (16)	0.0458 (14)	0.0089 (13)	0.0225 (13)	0.0112 (12)
C7	0.0367 (13)	0.0370 (14)	0.0378 (13)	0.0012 (11)	0.0082 (11)	−0.0018 (11)
C8	0.0475 (15)	0.0414 (14)	0.0409 (14)	−0.0031 (12)	0.0154 (12)	−0.0044 (11)
C9	0.0380 (13)	0.0400 (14)	0.0448 (14)	0.0016 (11)	0.0132 (12)	−0.0014 (11)
C10	0.0343 (13)	0.0357 (13)	0.0488 (14)	0.0047 (11)	0.0073 (12)	0.0041 (11)
C11	0.0409 (14)	0.0423 (14)	0.0418 (14)	0.0019 (11)	0.0151 (12)	0.0015 (11)
C12	0.0382 (13)	0.0410 (14)	0.0447 (15)	0.0020 (11)	0.0142 (12)	−0.0024 (11)
C13	0.0501 (15)	0.0550 (17)	0.0615 (17)	0.0064 (13)	0.0210 (14)	−0.0019 (13)
C14	0.0629 (17)	0.0611 (17)	0.0648 (17)	0.0094 (13)	0.0391 (15)	0.0066 (13)
C15	0.0652 (18)	0.075 (2)	0.083 (2)	0.0302 (16)	0.0231 (16)	0.0123 (16)
N1	0.0474 (12)	0.0456 (12)	0.0465 (12)	0.0083 (10)	0.0130 (11)	0.0045 (10)
N2	0.0449 (11)	0.0398 (12)	0.0446 (12)	0.0046 (9)	0.0121 (10)	−0.0004 (9)
O1	0.0616 (11)	0.0667 (11)	0.0538 (10)	0.0209 (9)	0.0297 (9)	0.0210 (9)
O2	0.0568 (11)	0.0640 (12)	0.0655 (11)	0.0252 (9)	0.0229 (9)	0.0186 (9)
O3	0.0699 (13)	0.0822 (14)	0.0913 (14)	0.0343 (11)	0.0393 (11)	0.0185 (12)
O4	0.0695 (13)	0.0786 (13)	0.0737 (13)	0.0366 (10)	0.0369 (11)	0.0243 (10)

Geometric parameters (Å, º)

C1—C6	1.371 (3)	C9—C13	1.447 (3)
C1—C2	1.392 (3)	C10—O2	1.349 (2)
C1—N1	1.433 (3)	C10—C11	1.402 (3)
C2—C3	1.376 (3)	C11—O1	1.355 (2)
C2—H2	0.93	C11—C12	1.371 (3)
C3—C4	1.380 (3)	C12—H12	0.93
C3—H3	0.93	C13—O3	1.224 (3)
C4—C5	1.376 (3)	C13—H13	0.93
C4—H4	0.93	C14—O1	1.432 (2)
C5—O4	1.361 (3)	C14—H14A	0.96
C5—C6	1.391 (3)	C14—H14B	0.96
C6—H6	0.93	C14—H14C	0.96
C7—C8	1.375 (3)	C15—O4	1.424 (3)
C7—C12	1.400 (3)	C15—H15A	0.96
C7—N2	1.423 (3)	C15—H15B	0.96
C8—C9	1.398 (3)	C15—H15C	0.96
C8—H8	0.93	N1—N2	1.255 (2)
C9—C10	1.395 (3)	O2—H1	0.82
C6—C1—C2	120.3 (2)	O2—C10—C11	117.8 (2)
C6—C1—N1	114.9 (2)	C9—C10—C11	120.3 (2)
C2—C1—N1	124.8 (2)	O1—C11—C12	125.5 (2)
C3—C2—C1	118.4 (2)	O1—C11—C10	114.8 (2)
C3—C2—H2	120.8	C12—C11—C10	119.7 (2)
C1—C2—H2	120.8	C11—C12—C7	120.6 (2)
C2—C3—C4	121.8 (2)	C11—C12—H12	119.7
C2—C3—H3	119.1	C7—C12—H12	119.7
C4—C3—H3	119.1	O3—C13—C9	123.4 (2)
C5—C4—C3	119.4 (2)	O3—C13—H13	118.3
C5—C4—H4	120.3	C9—C13—H13	118.3
C3—C4—H4	120.3	O1—C14—H14A	109.5
O4—C5—C4	125.1 (2)	O1—C14—H14B	109.5
O4—C5—C6	115.5 (2)	H14A—C14—H14B	109.5
C4—C5—C6	119.5 (2)	O1—C14—H14C	109.5
C1—C6—C5	120.6 (2)	H14A—C14—H14C	109.5
C1—C6—H6	119.7	H14B—C14—H14C	109.5
C5—C6—H6	119.7	O4—C15—H15A	109.5
C8—C7—C12	119.8 (2)	O4—C15—H15B	109.5
C8—C7—N2	116.4 (2)	H15A—C15—H15B	109.5
C12—C7—N2	123.8 (2)	O4—C15—H15C	109.5
C7—C8—C9	120.7 (2)	H15A—C15—H15C	109.5
C7—C8—H8	119.7	H15B—C15—H15C	109.5
C9—C8—H8	119.7	N2—N1—C1	114.27 (19)
C10—C9—C8	119.0 (2)	N1—N2—C7	113.97 (19)
C10—C9—C13	120.7 (2)	C11—O1—C14	117.09 (18)
C8—C9—C13	120.2 (2)	C10—O2—H1	109.5
O2—C10—C9	121.9 (2)	C5—O4—C15	118.2 (2)
C6—C1—C2—C3	−1.0 (3)	C9—C10—C11—O1	178.23 (19)
N1—C1—C2—C3	179.4 (2)	O2—C10—C11—C12	179.2 (2)
C1—C2—C3—C4	0.9 (3)	C9—C10—C11—C12	−0.8 (3)
C2—C3—C4—C5	−0.3 (3)	O1—C11—C12—C7	−178.4 (2)
C3—C4—C5—O4	179.8 (2)	C10—C11—C12—C7	0.5 (3)
C3—C4—C5—C6	−0.2 (3)	C8—C7—C12—C11	0.4 (3)
C2—C1—C6—C5	0.5 (3)	N2—C7—C12—C11	−179.7 (2)
N1—C1—C6—C5	−179.9 (2)	C10—C9—C13—O3	−1.5 (4)
O4—C5—C6—C1	−179.9 (2)	C8—C9—C13—O3	−179.9 (2)
C4—C5—C6—C1	0.1 (4)	C6—C1—N1—N2	174.7 (2)
C12—C7—C8—C9	−1.2 (3)	C2—C1—N1—N2	−5.8 (3)
N2—C7—C8—C9	178.96 (19)	C1—N1—N2—C7	179.80 (17)
C7—C8—C9—C10	0.8 (3)	C8—C7—N2—N1	179.30 (19)
C7—C8—C9—C13	179.3 (2)	C12—C7—N2—N1	−0.6 (3)
C8—C9—C10—O2	−179.93 (19)	C12—C11—O1—C14	1.5 (3)
C13—C9—C10—O2	1.7 (3)	C10—C11—O1—C14	−177.6 (2)
C8—C9—C10—C11	0.2 (3)	C4—C5—O4—C15	−1.9 (3)
C13—C9—C10—C11	−178.2 (2)	C6—C5—O4—C15	178.1 (2)
O2—C10—C11—O1	−1.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O3	0.82	1.89	2.606 (2)	146
C14—H14A···O4^i	0.96	2.49	3.188 (3)	130
C14—H14C···O3^ii	0.96	2.54	3.398 (3)	148
C14—H14B···Cg1^iii	0.96	2.83	3.667 (2)	147

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