(E)-5-(4-Ethyl­phenyl­diazen­yl)salicylaldehyde

The molecule of the title compound, C₁₅H₁₄N₂O₂, is approximately planar and displays a trans configuration with respect to the N=N double bond. The dihedral angle between the two aromatic rings is 10.90 (14)°. The mol­ecules are stacked via weak C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.144
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................      10.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C10    -   C11    ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C11    -   C12    ...       1.38 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CG14    ..       3.14 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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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); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-5-(4-Ethylphenyldiazenyl)salicylaldehyde

Crystal data

C15H14N2O2	F(000) = 536
Mr = 254.28	Dx = 1.282 Mg m^−3
Monoclinic, P21/c	Melting point = 396–399 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.2617 (12) Å	Cell parameters from 2588 reflections
b = 13.731 (2) Å	θ = 2.1–25.2°
c = 6.776 (3) Å	µ = 0.09 mm^−1
β = 96.958 (14)°	T = 296 K
V = 1317.2 (5) Å^3	Plate, yellow
Z = 4	0.50 × 0.31 × 0.07 mm

Data collection

Stoe IPDS-2 diffractometer	2588 independent reflections
Radiation source: fine-focus sealed tube	852 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −17→17
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→16
Tmin = 0.947, Tmax = 0.992	l = −8→8
9050 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ^2(Fo^2) + (0.0616P)^2] where P = (Fo^2 + 2Fc^2)/3
2588 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.12 e Å^−3
1 restraint	Δρmin = −0.10 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	Occ. (<1)
C1	0.2830 (2)	0.63574 (19)	0.7142 (5)	0.0875 (9)
C2	0.3042 (2)	0.6199 (2)	0.9175 (5)	0.0968 (9)
C3	0.3942 (2)	0.6062 (2)	1.0001 (5)	0.1113 (11)
H3	0.4076	0.5949	1.1359	0.134*
C4	0.4655 (2)	0.6092 (2)	0.8821 (5)	0.0961 (9)
H4	0.5275	0.6005	0.9402	0.115*
C5	0.4487 (2)	0.62479 (18)	0.6805 (4)	0.0779 (8)
C6	0.3577 (2)	0.63832 (19)	0.5970 (4)	0.0891 (9)
H6	0.3450	0.6494	0.4610	0.107*
C7	0.1882 (2)	0.6494 (2)	0.6250 (6)	0.1181 (12)
H7	0.1787	0.6590	0.4881	0.142*
C8	0.6722 (2)	0.61283 (19)	0.5065 (4)	0.0785 (8)
C9	0.7602 (2)	0.5852 (2)	0.5936 (4)	0.0986 (9)
H9	0.7679	0.5626	0.7239	0.118*
C10	0.8374 (2)	0.5907 (3)	0.4894 (6)	0.1202 (12)
H10	0.8966	0.5723	0.5507	0.144*
C11	0.8278 (3)	0.6231 (3)	0.2961 (7)	0.1274 (13)
C12	0.7392 (3)	0.6505 (2)	0.2107 (5)	0.1147 (11)
H12	0.7313	0.6727	0.0800	0.138*
C13	0.6623 (2)	0.6459 (2)	0.3139 (5)	0.0908 (9)
H13	0.6033	0.6652	0.2532	0.109*
C14A	0.9154 (13)	0.6618 (12)	0.197 (3)	0.163 (4)	0.478 (9)
H14A	0.8932	0.6994	0.0787	0.195*	0.478 (9)
H14B	0.9533	0.7043	0.2887	0.195*	0.478 (9)
C14B	0.9031 (12)	0.6027 (9)	0.150 (3)	0.163 (4)	0.522 (9)
H14C	0.9171	0.5336	0.1465	0.195*	0.522 (9)
H14D	0.8799	0.6241	0.0169	0.195*	0.522 (9)
C15A	0.9680 (10)	0.5879 (11)	0.147 (3)	0.201 (4)	0.478 (9)
H15A	1.0244	0.6126	0.1009	0.301*	0.478 (9)
H15B	0.9329	0.5506	0.0431	0.301*	0.478 (9)
H15C	0.9845	0.5471	0.2608	0.301*	0.478 (9)
C15B	0.9842 (10)	0.6554 (10)	0.225 (2)	0.201 (4)	0.522 (9)
H15D	1.0324	0.6459	0.1392	0.301*	0.522 (9)
H15E	1.0066	0.6328	0.3560	0.301*	0.522 (9)
H15F	0.9689	0.7233	0.2295	0.301*	0.522 (9)
N1	0.52041 (18)	0.62813 (15)	0.5508 (3)	0.0830 (7)
N2	0.59986 (19)	0.60685 (16)	0.6323 (3)	0.0855 (7)
O1	0.11825 (16)	0.64973 (17)	0.7128 (4)	0.1391 (10)
O2	0.2328 (2)	0.6169 (2)	1.0378 (5)	0.1331 (9)
H2	0.191 (3)	0.615 (5)	0.942 (7)	0.28 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.075 (2)	0.087 (2)	0.103 (2)	0.0051 (16)	0.0173 (19)	0.0022 (18)
C2	0.093 (2)	0.096 (2)	0.107 (3)	0.0101 (18)	0.031 (2)	0.003 (2)
C3	0.107 (3)	0.147 (3)	0.082 (2)	0.018 (2)	0.019 (2)	0.010 (2)
C4	0.095 (2)	0.112 (2)	0.083 (2)	0.0090 (18)	0.0205 (18)	−0.0011 (19)
C5	0.079 (2)	0.0806 (19)	0.076 (2)	0.0031 (16)	0.0196 (16)	0.0023 (16)
C6	0.086 (2)	0.093 (2)	0.091 (2)	0.0057 (17)	0.0206 (19)	0.0002 (16)
C7	0.084 (2)	0.132 (3)	0.140 (3)	0.015 (2)	0.021 (2)	0.008 (2)
C8	0.0717 (18)	0.0836 (19)	0.082 (2)	−0.0065 (15)	0.0179 (16)	−0.0001 (16)
C9	0.082 (2)	0.123 (2)	0.092 (2)	0.0065 (18)	0.0137 (18)	0.0126 (18)
C10	0.069 (2)	0.158 (3)	0.135 (3)	0.015 (2)	0.017 (2)	0.016 (3)
C11	0.092 (2)	0.155 (3)	0.142 (4)	0.002 (2)	0.041 (3)	0.019 (3)
C12	0.122 (3)	0.134 (3)	0.094 (2)	0.002 (2)	0.034 (2)	0.021 (2)
C13	0.0802 (19)	0.101 (2)	0.093 (2)	0.0057 (15)	0.0157 (18)	0.0060 (17)
C14A	0.100 (5)	0.172 (12)	0.232 (11)	−0.017 (10)	0.082 (7)	−0.002 (11)
C14B	0.100 (5)	0.172 (12)	0.232 (11)	−0.017 (10)	0.082 (7)	−0.002 (11)
C15A	0.126 (6)	0.201 (12)	0.297 (13)	−0.042 (8)	0.111 (8)	−0.047 (9)
C15B	0.126 (6)	0.201 (12)	0.297 (13)	−0.042 (8)	0.111 (8)	−0.047 (9)
N1	0.0744 (16)	0.0886 (17)	0.0864 (17)	0.0003 (13)	0.0115 (14)	−0.0036 (13)
N2	0.0778 (16)	0.0908 (16)	0.0885 (18)	−0.0001 (14)	0.0121 (14)	−0.0008 (13)
O1	0.0918 (16)	0.161 (2)	0.171 (3)	0.0201 (14)	0.0451 (17)	0.0126 (17)
O2	0.121 (2)	0.155 (2)	0.136 (2)	0.0082 (17)	0.0678 (18)	0.0070 (18)

Geometric parameters (Å, º)

C1—C2	1.392 (4)	C11—C12	1.378 (4)
C1—C6	1.404 (3)	C11—C14B	1.570 (15)
C1—C7	1.425 (4)	C11—C14A	1.581 (15)
C2—C3	1.350 (4)	C12—C13	1.371 (4)
C2—O2	1.380 (3)	C12—H12	0.9300
C3—C4	1.369 (4)	C13—H13	0.9300
C3—H3	0.9300	C14A—C15A	1.33 (3)
C4—C5	1.375 (3)	C14A—H14A	0.9700
C4—H4	0.9300	C14A—H14B	0.9700
C5—C6	1.364 (4)	C14B—C15B	1.40 (3)
C5—N1	1.428 (3)	C14B—H14C	0.9700
C6—H6	0.9300	C14B—H14D	0.9700
C7—O1	1.222 (3)	C15A—H15A	0.9600
C7—H7	0.9300	C15A—H15B	0.9600
C8—C13	1.373 (4)	C15A—H15C	0.9600
C8—C9	1.375 (4)	C15B—H15D	0.9600
C8—N2	1.418 (3)	C15B—H15E	0.9600
C9—C10	1.379 (4)	C15B—H15F	0.9600
C9—H9	0.9300	N1—N2	1.234 (3)
C10—C11	1.375 (5)	O2—H2	0.82 (2)
C10—H10	0.9300
C2—C1—C6	118.4 (3)	C10—C11—C14B	123.1 (8)
C2—C1—C7	121.5 (3)	C12—C11—C14B	116.6 (9)
C6—C1—C7	120.2 (3)	C10—C11—C14A	121.6 (9)
C3—C2—O2	118.9 (4)	C12—C11—C14A	117.4 (9)
C3—C2—C1	120.9 (3)	C13—C12—C11	121.5 (3)
O2—C2—C1	120.1 (4)	C13—C12—H12	119.3
C2—C3—C4	119.3 (3)	C11—C12—H12	119.3
C2—C3—H3	120.3	C12—C13—C8	120.3 (3)
C4—C3—H3	120.3	C12—C13—H13	119.9
C3—C4—C5	122.2 (3)	C8—C13—H13	119.9
C3—C4—H4	118.9	C15A—C14A—C11	110.5 (13)
C5—C4—H4	118.9	C15A—C14A—H14A	109.6
C6—C5—C4	118.5 (3)	C11—C14A—H14A	109.6
C6—C5—N1	117.2 (3)	C15A—C14A—H14B	109.6
C4—C5—N1	124.3 (3)	C11—C14A—H14B	109.6
C5—C6—C1	120.7 (3)	H14A—C14A—H14B	108.1
C5—C6—H6	119.6	C15B—C14B—C11	106.1 (13)
C1—C6—H6	119.6	C15B—C14B—H14C	110.5
O1—C7—C1	125.6 (4)	C11—C14B—H14C	110.5
O1—C7—H7	117.2	C15B—C14B—H14D	110.5
C1—C7—H7	117.2	C11—C14B—H14D	110.5
C13—C8—C9	118.8 (2)	H14C—C14B—H14D	108.7
C13—C8—N2	126.4 (3)	C14B—C15B—H15D	109.5
C9—C8—N2	114.8 (3)	C14B—C15B—H15E	109.5
C8—C9—C10	120.6 (3)	H15D—C15B—H15E	109.5
C8—C9—H9	119.7	C14B—C15B—H15F	109.5
C10—C9—H9	119.7	H15D—C15B—H15F	109.5
C11—C10—C9	120.8 (3)	H15E—C15B—H15F	109.5
C11—C10—H10	119.6	N2—N1—C5	113.9 (3)
C9—C10—H10	119.6	N1—N2—C8	114.4 (3)
C10—C11—C12	118.0 (3)	C2—O2—H2	93 (5)
C6—C1—C2—C3	−0.7 (4)	C9—C10—C11—C14B	−161.2 (7)
C7—C1—C2—C3	179.5 (3)	C9—C10—C11—C14A	160.2 (7)
C6—C1—C2—O2	179.9 (3)	C10—C11—C12—C13	−0.1 (6)
C7—C1—C2—O2	0.1 (4)	C14B—C11—C12—C13	162.9 (6)
O2—C2—C3—C4	−179.9 (3)	C14A—C11—C12—C13	−160.6 (7)
C1—C2—C3—C4	0.8 (5)	C11—C12—C13—C8	−0.4 (5)
C2—C3—C4—C5	−0.7 (5)	C9—C8—C13—C12	0.4 (4)
C3—C4—C5—C6	0.5 (5)	N2—C8—C13—C12	178.0 (3)
C3—C4—C5—N1	−179.7 (3)	C10—C11—C14A—C15A	76.8 (17)
C4—C5—C6—C1	−0.4 (4)	C12—C11—C14A—C15A	−123.5 (15)
N1—C5—C6—C1	179.8 (2)	C14B—C11—C14A—C15A	−26.4 (19)
C2—C1—C6—C5	0.5 (4)	C10—C11—C14B—C15B	−67.4 (13)
C7—C1—C6—C5	−179.6 (3)	C12—C11—C14B—C15B	130.6 (12)
C2—C1—C7—O1	0.7 (5)	C14A—C11—C14B—C15B	31 (2)
C6—C1—C7—O1	−179.1 (3)	C6—C5—N1—N2	−173.9 (3)
C13—C8—C9—C10	0.1 (4)	C4—C5—N1—N2	6.3 (4)
N2—C8—C9—C10	−177.8 (3)	C5—N1—N2—C8	−178.2 (2)
C8—C9—C10—C11	−0.5 (5)	C13—C8—N2—N1	4.9 (4)
C9—C10—C11—C12	0.5 (6)	C9—C8—N2—N1	−177.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.82 (2)	1.83 (3)	2.618 (5)	161 (7)
C12—H12···Cg(14)^i	0.93	3.14	3.819 (3)	131

Symmetry code: (i) x, −y−1/2, z−1/2.