4-(Diethyl­amino)salicylaldehyde

The title compound, C₁₁H₁₅NO₂, contains a planar diethyl­amine group with an sp²-hybridized N atom bonded to a nearly planar salicylaldehyde fragment. Electron density from the diethyl­amine group is transferred to a pseudo-ring formed by an intra­molecular O—H...O hydrogen bond involving the aldehyde and hydr­oxy groups. In the crystal structure, the mol­ecules form C—H...O hydrogen-bonded centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.103
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Johnson & Burnett, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

4-(Diethylamino)salicylaldehyde

Crystal data

C11H15NO2	Z = 2
Mr = 193.24	F(000) = 208
Triclinic, P1	Dx = 1.282 Mg m^−3
Hall symbol: -P 1	Melting point: 335 K
a = 7.0605 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1633 (11) Å	Cell parameters from 2035 reflections
c = 9.2352 (13) Å	θ = 2.3–28.3°
α = 94.103 (11)°	µ = 0.09 mm^−1
β = 107.421 (13)°	T = 120 K
γ = 97.215 (12)°	Prism, light brown
V = 500.49 (12) Å^3	0.40 × 0.40 × 0.15 mm

Data collection

Kuma KM-4 CCD area-detector diffractometer	1454 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Oxford Enhance monochromator	θmax = 25.0°, θmin = 3.1°
Detector resolution: 16.3 pixels mm^-1	h = −8→7
rotation method, ω scans	k = −9→9
3791 measured reflections	l = −10→10
1755 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0625P)^2 + 0.03P] where P = (Fo^2 + 2Fc^2)/3
1755 reflections	(Δ/σ)max = 0.017
133 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.25 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
O1	0.58345 (13)	0.35453 (11)	0.19320 (10)	0.0265 (3)
O2	0.62628 (13)	0.14626 (11)	0.39828 (10)	0.0293 (3)
N	0.06003 (14)	0.68561 (12)	0.13923 (11)	0.0187 (3)
C1	0.43233 (17)	0.40189 (14)	0.24174 (14)	0.0189 (3)
C2	0.38128 (17)	0.32555 (15)	0.36111 (14)	0.0199 (3)
C3	0.22450 (18)	0.38096 (15)	0.40636 (14)	0.0216 (3)
H3	0.1887	0.3332	0.4872	0.026*
C4	0.12171 (18)	0.50069 (15)	0.33860 (14)	0.0207 (3)
H4	0.0179	0.5354	0.3735	0.025*
C5	0.16978 (17)	0.57428 (14)	0.21499 (13)	0.0176 (3)
C6	0.33164 (17)	0.52363 (14)	0.17191 (13)	0.0186 (3)
H6	0.3715	0.5741	0.0939	0.022*
C7	0.48764 (19)	0.20086 (15)	0.43385 (14)	0.0247 (3)
H7	0.4498	0.1565	0.5152	0.030*
C8	0.11626 (17)	0.76563 (15)	0.01751 (14)	0.0210 (3)
H8A	−0.0013	0.8100	−0.0463	0.025*
H8B	0.1503	0.6806	−0.0485	0.025*
C9	0.29331 (18)	0.90662 (16)	0.07567 (16)	0.0273 (3)
H9A	0.2592	0.9937	0.1378	0.041*
H9B	0.3235	0.9530	−0.0114	0.041*
H9C	0.4111	0.8638	0.1380	0.041*
C10	−0.11158 (17)	0.73782 (15)	0.17904 (14)	0.0209 (3)
H10A	−0.1781	0.6438	0.2171	0.025*
H10B	−0.2100	0.7640	0.0854	0.025*
C11	−0.05510 (19)	0.88843 (16)	0.29930 (14)	0.0266 (3)
H11A	0.0430	0.8642	0.3924	0.040*
H11B	−0.1756	0.9139	0.3226	0.040*
H11C	0.0036	0.9841	0.2603	0.040*
H1	0.636 (2)	0.2728 (17)	0.2524 (17)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0241 (5)	0.0267 (5)	0.0365 (6)	0.0112 (4)	0.0167 (4)	0.0091 (4)
O2	0.0287 (5)	0.0254 (5)	0.0344 (6)	0.0115 (4)	0.0075 (4)	0.0040 (4)
N	0.0187 (5)	0.0187 (5)	0.0205 (5)	0.0046 (4)	0.0078 (4)	0.0049 (4)
C1	0.0160 (6)	0.0179 (6)	0.0221 (6)	0.0005 (5)	0.0067 (5)	−0.0024 (5)
C2	0.0220 (6)	0.0165 (6)	0.0192 (6)	0.0018 (5)	0.0040 (5)	0.0008 (5)
C3	0.0268 (6)	0.0206 (6)	0.0193 (6)	0.0031 (5)	0.0101 (5)	0.0034 (5)
C4	0.0224 (6)	0.0215 (6)	0.0213 (7)	0.0046 (5)	0.0109 (5)	0.0021 (5)
C5	0.0179 (6)	0.0143 (6)	0.0184 (6)	0.0001 (5)	0.0040 (5)	−0.0006 (5)
C6	0.0195 (6)	0.0180 (6)	0.0192 (6)	0.0007 (5)	0.0077 (5)	0.0036 (5)
C7	0.0281 (7)	0.0209 (7)	0.0236 (7)	0.0046 (5)	0.0058 (5)	0.0022 (5)
C8	0.0201 (6)	0.0227 (7)	0.0212 (6)	0.0040 (5)	0.0068 (5)	0.0067 (5)
C9	0.0253 (7)	0.0238 (7)	0.0345 (8)	0.0023 (5)	0.0116 (6)	0.0073 (6)
C10	0.0193 (6)	0.0213 (6)	0.0245 (7)	0.0065 (5)	0.0081 (5)	0.0062 (5)
C11	0.0289 (7)	0.0276 (7)	0.0269 (7)	0.0091 (5)	0.0121 (6)	0.0026 (5)

Geometric parameters (Å, º)

O1—C1	1.3617 (14)	C6—H6	0.9500
O1—H1	0.934 (9)	C7—H7	0.9500
O2—C7	1.2433 (15)	C8—C9	1.5244 (17)
N—C5	1.3635 (15)	C8—H8A	0.9900
N—C8	1.4680 (14)	C8—H8B	0.9900
N—C10	1.4694 (14)	C9—H9A	0.9800
C1—C6	1.3796 (17)	C9—H9B	0.9800
C1—C2	1.4189 (17)	C9—H9C	0.9800
C2—C3	1.4072 (16)	C10—C11	1.5233 (18)
C2—C7	1.4280 (17)	C10—H10A	0.9900
C3—C4	1.3665 (17)	C10—H10B	0.9900
C3—H3	0.9500	C11—H11A	0.9800
C4—C5	1.4346 (16)	C11—H11B	0.9800
C4—H4	0.9500	C11—H11C	0.9800
C5—C6	1.4152 (16)
C1—O1—H1	107.5 (10)	N—C8—C9	113.96 (10)
C5—N—C8	120.60 (9)	N—C8—H8A	108.8
C5—N—C10	122.54 (9)	C9—C8—H8A	108.8
C8—N—C10	116.78 (9)	N—C8—H8B	108.8
O1—C1—C6	118.51 (10)	C9—C8—H8B	108.8
O1—C1—C2	119.85 (11)	H8A—C8—H8B	107.7
C6—C1—C2	121.63 (11)	C8—C9—H9A	109.5
C3—C2—C1	116.95 (11)	C8—C9—H9B	109.5
C3—C2—C7	121.76 (11)	H9A—C9—H9B	109.5
C1—C2—C7	121.27 (11)	C8—C9—H9C	109.5
C4—C3—C2	122.58 (11)	H9A—C9—H9C	109.5
C4—C3—H3	118.7	H9B—C9—H9C	109.5
C2—C3—H3	118.7	N—C10—C11	113.93 (10)
C3—C4—C5	120.35 (11)	N—C10—H10A	108.8
C3—C4—H4	119.8	C11—C10—H10A	108.8
C5—C4—H4	119.8	N—C10—H10B	108.8
N—C5—C6	121.26 (10)	C11—C10—H10B	108.8
N—C5—C4	121.15 (11)	H10A—C10—H10B	107.7
C6—C5—C4	117.56 (11)	C10—C11—H11A	109.5
C1—C6—C5	120.85 (10)	C10—C11—H11B	109.5
C1—C6—H6	119.6	H11A—C11—H11B	109.5
C5—C6—H6	119.6	C10—C11—H11C	109.5
O2—C7—C2	124.66 (11)	H11A—C11—H11C	109.5
O2—C7—H7	117.7	H11B—C11—H11C	109.5
C2—C7—H7	117.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.93 (1)	1.77 (1)	2.6107 (12)	149 (2)
C11—H11A···O2^i	0.98	2.56	3.5090 (17)	162

Symmetry code: (i) −x+1, −y+1, −z+1.