6-[(2,4-Di-methyl-anilino)methyl-idene]-2-hy-droxy-cyclo-hexa-2,4-dienone.

In the title compound, C15H15NO2, the dihedral angle between the aromatic rings is 5.86 (6)°, and an intra-molecular N-H⋯O hydrogen bond generates an S(6) motif, which helps to stabilize the enamine-keto tautomer. An intra-molecular O-H⋯O hydrogen bond also occurs. In the crystal, inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 (2)(10) loops. A C-H⋯O inter-action links the dimers into [010] chains and aromatic π-π stacking [centroid-centroid separation = 3.6131 (9) Å] also occurs.

Related literature

For a related structure and background to Schiff bases, see: Shuja et al. (2007 ▶). For further structural aspects, see: Blagus & Kaitner (2011 ▶).

Experimental

Crystal data

C15H15NO2

M = 241.28

Triclinic,

a = 7.6731 (8) Å

b = 8.4348 (9) Å

c = 10.5806 (12) Å

α = 80.6107 (18)°

β = 75.8216 (19)°

γ = 63.3573 (16)°

V = 592.31 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.53 × 0.48 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.943, T max = 0.974

4681 measured reflections

2363 independent reflections

2148 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.09

2363 reflections

223 parameters

All H-atom parameters refined

Δρmax = 0.29 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2006 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLUTO (Meetsma, 2006 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012233/hb7078sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012233/hb7078Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012233/hb7078Isup3.cml

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

C15H15NO2	Z = 2
Mr = 241.28	F(000) = 256
Triclinic, P1	The final unit cell was obtained from the xyz centroids of 3645 reflections after integration using the SAINTPLUS software package (Bruker, 2000).
Hall symbol: -P 1	Dx = 1.353 Mg m−3
a = 7.6731 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4348 (9) Å	Cell parameters from 3645 reflections
c = 10.5806 (12) Å	θ = 2.7–29.6°
α = 80.6107 (18)°	µ = 0.09 mm−1
β = 75.8216 (19)°	T = 100 K
γ = 63.3573 (16)°	Block, red
V = 592.31 (11) Å3	0.53 × 0.48 × 0.29 mm

Bruker SMART APEX CCD area-detector diffractometer	2363 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2148 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.009
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1	θmax = 26.4°, θmin = 2.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −10→10
Tmin = 0.943, Tmax = 0.974	l = −13→13
4681 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	All H-atom parameters refined
S = 1.09	w = 1/[σ2(Fo2) + (0.0825P)2 + 0.0862P] where P = (Fo2 + 2Fc2)/3
2363 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.14548 (13)	0.99696 (10)	0.64979 (8)	0.0261 (3)
O2	0.14914 (11)	0.77675 (9)	0.48083 (7)	0.0213 (2)
N1	0.23552 (13)	0.45820 (12)	0.42735 (8)	0.0179 (3)
C1	0.29515 (15)	0.40370 (14)	0.53911 (10)	0.0198 (3)
C2	0.28631 (15)	0.52113 (14)	0.62454 (10)	0.0180 (3)
C3	0.35444 (16)	0.45246 (14)	0.74426 (10)	0.0214 (3)
C4	0.35457 (16)	0.56226 (14)	0.82597 (10)	0.0217 (3)
C5	0.28454 (16)	0.74722 (14)	0.79198 (10)	0.0209 (3)
C6	0.21286 (16)	0.81822 (14)	0.67902 (10)	0.0195 (3)
C7	0.21212 (15)	0.70814 (14)	0.58908 (10)	0.0178 (3)
C8	0.23908 (15)	0.35066 (13)	0.33599 (10)	0.0173 (3)
C9	0.18384 (15)	0.43224 (13)	0.21664 (10)	0.0182 (3)
C10	0.18940 (16)	0.32622 (14)	0.12556 (10)	0.0194 (3)
C11	0.24356 (16)	0.14426 (14)	0.15117 (10)	0.0203 (3)
C12	0.29389 (16)	0.06799 (14)	0.27204 (11)	0.0215 (3)
C13	0.29397 (16)	0.16855 (14)	0.36332 (10)	0.0201 (3)
C14	0.11771 (17)	0.62921 (14)	0.18686 (10)	0.0220 (3)
C15	0.24119 (18)	0.03446 (15)	0.05288 (12)	0.0250 (3)
H1	0.351 (2)	0.273 (2)	0.5651 (14)	0.034 (4)*
H3	0.400 (2)	0.323 (2)	0.7672 (15)	0.042 (4)*
H4	0.401 (2)	0.5179 (18)	0.9075 (14)	0.027 (3)*
H5	0.286 (2)	0.8279 (19)	0.8468 (14)	0.031 (4)*
H10	0.1540 (19)	0.3814 (17)	0.0398 (13)	0.024 (3)*
H12	0.326 (2)	−0.062 (2)	0.2955 (14)	0.036 (4)*
H13	0.328 (2)	0.1118 (18)	0.4479 (13)	0.026 (3)*
H14	0.218 (2)	0.6672 (19)	0.1967 (14)	0.037 (4)*
H14'	0.096 (2)	0.6606 (19)	0.0969 (14)	0.033 (4)*
H14"	−0.010 (2)	0.6970 (19)	0.2456 (14)	0.033 (4)*
H15	0.251 (3)	0.088 (2)	−0.0373 (18)	0.049 (5)*
H15'	0.353 (2)	−0.084 (2)	0.0470 (16)	0.047 (4)*
H15"	0.122 (3)	0.016 (2)	0.0749 (16)	0.046 (4)*
H21	0.076 (3)	1.025 (2)	0.5909 (19)	0.052 (5)*
H31	0.187 (3)	0.590 (3)	0.412 (2)	0.088 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0360 (5)	0.0169 (4)	0.0268 (4)	−0.0088 (3)	−0.0143 (4)	−0.0005 (3)
O2	0.0259 (4)	0.0177 (4)	0.0188 (4)	−0.0070 (3)	−0.0078 (3)	0.0007 (3)
N1	0.0187 (5)	0.0161 (4)	0.0183 (4)	−0.0068 (3)	−0.0035 (3)	−0.0018 (3)
C1	0.0189 (5)	0.0172 (5)	0.0211 (5)	−0.0060 (4)	−0.0037 (4)	−0.0011 (4)
C2	0.0169 (5)	0.0176 (5)	0.0178 (5)	−0.0058 (4)	−0.0031 (4)	−0.0015 (4)
C3	0.0210 (5)	0.0194 (5)	0.0207 (5)	−0.0057 (4)	−0.0053 (4)	−0.0002 (4)
C4	0.0188 (5)	0.0251 (5)	0.0185 (5)	−0.0061 (4)	−0.0057 (4)	−0.0009 (4)
C5	0.0201 (5)	0.0239 (5)	0.0191 (5)	−0.0086 (4)	−0.0034 (4)	−0.0051 (4)
C6	0.0190 (5)	0.0173 (5)	0.0211 (5)	−0.0069 (4)	−0.0028 (4)	−0.0028 (4)
C7	0.0157 (5)	0.0193 (5)	0.0169 (5)	−0.0066 (4)	−0.0026 (4)	−0.0009 (4)
C8	0.0156 (5)	0.0175 (5)	0.0188 (5)	−0.0070 (4)	−0.0025 (4)	−0.0029 (4)
C9	0.0167 (5)	0.0170 (5)	0.0200 (5)	−0.0067 (4)	−0.0030 (4)	−0.0014 (4)
C10	0.0192 (5)	0.0206 (5)	0.0187 (5)	−0.0083 (4)	−0.0043 (4)	−0.0014 (4)
C11	0.0180 (5)	0.0200 (5)	0.0233 (5)	−0.0081 (4)	−0.0021 (4)	−0.0055 (4)
C12	0.0206 (5)	0.0169 (5)	0.0259 (5)	−0.0073 (4)	−0.0045 (4)	−0.0010 (4)
C13	0.0204 (5)	0.0177 (5)	0.0215 (5)	−0.0074 (4)	−0.0053 (4)	0.0001 (4)
C14	0.0283 (6)	0.0172 (5)	0.0204 (5)	−0.0084 (4)	−0.0083 (4)	0.0002 (4)
C15	0.0275 (6)	0.0221 (5)	0.0272 (6)	−0.0102 (5)	−0.0064 (4)	−0.0061 (4)

O1—C6	1.3649 (13)	C10—C11	1.3961 (15)
O2—C7	1.2978 (13)	C11—C12	1.3961 (16)
O1—H21	0.85 (2)	C11—C15	1.5094 (17)
N1—C1	1.3107 (14)	C12—C13	1.3857 (16)
N1—C8	1.4174 (14)	C1—H1	1.005 (15)
N1—H31	1.00 (2)	C3—H3	0.993 (15)
C1—C2	1.4158 (16)	C4—H4	0.968 (15)
C2—C3	1.4237 (15)	C5—H5	0.969 (15)
C2—C7	1.4350 (15)	C10—H10	0.992 (14)
C3—C4	1.3666 (16)	C12—H12	1.012 (15)
C4—C5	1.4184 (15)	C13—H13	0.980 (14)
C5—C6	1.3721 (16)	C14—H14	0.988 (17)
C6—C7	1.4365 (16)	C14—H14'	0.980 (15)
C8—C9	1.4018 (15)	C14—H14"	0.994 (15)
C8—C13	1.3982 (15)	C15—H15	0.987 (18)
C9—C14	1.5061 (15)	C15—H15'	0.982 (16)
C9—C10	1.3989 (15)	C15—H15"	0.96 (2)
O1···O2	2.7674 (12)	C4···H14iv	2.938 (16)
O1···C13i	3.3069 (14)	C4···H14'vi	3.059 (15)
O1···O2ii	2.7320 (13)	C5···H15"iii	2.98 (2)
O1···C14ii	3.3713 (14)	C7···H31	2.35 (2)
O2···O1ii	2.7320 (13)	C12···H3vii	3.096 (15)
O2···C12i	3.4092 (14)	C13···H21v	2.99 (2)
O2···O1	2.7674 (12)	C13···H1	2.635 (15)
O2···N1	2.5873 (12)	C14···H31	2.50 (2)
O2···C13iii	3.2538 (16)	C15···H5viii	2.871 (15)
O1···H13i	2.557 (14)	H1···C13	2.635 (15)
O1···H14"ii	2.633 (14)	H1···H3	2.39 (2)
O2···H31	1.72 (2)	H1···H13	2.07 (2)
O2···H12i	2.649 (16)	H3···H1	2.39 (2)
O2···H21	2.340 (17)	H3···C12vii	3.096 (15)
O2···H21ii	1.999 (19)	H3···H12vii	2.31 (2)
N1···O2	2.5873 (12)	H5···C15ix	2.871 (15)
N1···H14	2.762 (14)	H5···H15ix	2.57 (2)
N1···H14"	2.900 (15)	H5···H15'ix	2.59 (2)
C1···C2iv	3.5296 (18)	H10···C4x	3.015 (14)
C1···C7iv	3.4250 (18)	H10···H14'	2.35 (2)
C2···C9iii	3.4592 (18)	H10···H15	2.46 (2)
C2···C1iv	3.5296 (18)	H10···H10xi	2.55 (2)
C2···C2iv	3.5848 (17)	H12···O2v	2.649 (16)
C4···C9iv	3.4797 (19)	H12···H3vii	2.31 (2)
C4···C8iv	3.4962 (18)	H13···O1v	2.557 (14)
C5···C13iv	3.5694 (19)	H13···C1	2.675 (14)
C5···C8iv	3.3332 (18)	H13···H1	2.07 (2)
C6···C12iii	3.4839 (19)	H13···H21v	2.46 (3)
C6···C11iii	3.4209 (19)	H14···N1	2.762 (14)
C7···C12iii	3.5121 (18)	H14···H31	2.25 (3)
C7···C13iii	3.4649 (19)	H14···C4iv	2.938 (16)
C7···C1iv	3.4250 (18)	H14'···C4x	3.059 (15)
C7···C8iii	3.5955 (18)	H14'···H10	2.35 (2)
C8···C5iv	3.3332 (18)	H14"···N1	2.900 (15)
C8···C4iv	3.4962 (18)	H14"···H31	2.40 (3)
C8···C7iii	3.5955 (18)	H14"···O1ii	2.633 (14)
C9···C2iii	3.4592 (18)	H14"···C1iii	3.048 (16)
C9···C4iv	3.4797 (19)	H15···H5viii	2.57 (2)
C11···C6iii	3.4209 (19)	H15···H10	2.46 (2)
C12···C7iii	3.5121 (18)	H15'···H5viii	2.59 (2)
C12···O2v	3.4092 (14)	H15"···C5iii	2.98 (2)
C12···C6iii	3.4839 (19)	H21···O2	2.340 (17)
C13···C5iv	3.5694 (19)	H21···C13i	2.99 (2)
C13···C7iii	3.4649 (19)	H21···H13i	2.46 (3)
C13···O2iii	3.2538 (16)	H21···O2ii	2.00 (2)
C13···O1v	3.3069 (14)	H31···O2	1.72 (2)
C14···O1ii	3.3713 (14)	H31···C7	2.35 (2)
C1···H14"iii	3.048 (16)	H31···C14	2.50 (2)
C1···H13	2.675 (14)	H31···H14	2.25 (3)
C4···H10vi	3.015 (14)	H31···H14"	2.40 (3)
C6—O1—H21	108.2 (11)	C8—C13—C12	119.90 (10)
C1—N1—C8	126.62 (9)	N1—C1—H1	118.8 (9)
C1—N1—H31	110.9 (13)	C2—C1—H1	118.4 (9)
C8—N1—H31	122.5 (12)	C2—C3—H3	118.1 (9)
N1—C1—C2	122.78 (10)	C4—C3—H3	121.0 (9)
C1—C2—C3	119.73 (10)	C3—C4—H4	122.0 (8)
C1—C2—C7	119.92 (10)	C5—C4—H4	118.2 (8)
C3—C2—C7	120.35 (10)	C4—C5—H5	121.7 (9)
C2—C3—C4	120.82 (10)	C6—C5—H5	117.5 (9)
C3—C4—C5	119.78 (10)	C9—C10—H10	119.3 (8)
C4—C5—C6	120.82 (10)	C11—C10—H10	118.6 (8)
O1—C6—C5	119.25 (10)	C11—C12—H12	119.8 (9)
O1—C6—C7	119.23 (10)	C13—C12—H12	118.9 (9)
C5—C6—C7	121.50 (10)	C8—C13—H13	120.6 (8)
C2—C7—C6	116.70 (10)	C12—C13—H13	119.5 (8)
O2—C7—C2	122.55 (10)	C9—C14—H14	111.6 (8)
O2—C7—C6	120.74 (9)	C9—C14—H14'	109.8 (9)
N1—C8—C13	121.55 (9)	C9—C14—H14"	110.7 (8)
N1—C8—C9	118.11 (9)	H14—C14—H14'	108.3 (13)
C9—C8—C13	120.34 (10)	H14—C14—H14"	108.7 (13)
C8—C9—C10	118.30 (9)	H14'—C14—H14"	107.6 (13)
C8—C9—C14	121.27 (9)	C11—C15—H15	113.3 (11)
C10—C9—C14	120.43 (9)	C11—C15—H15'	113.3 (10)
C9—C10—C11	122.16 (10)	C11—C15—H15"	111.1 (10)
C10—C11—C15	120.97 (10)	H15—C15—H15'	104.2 (14)
C10—C11—C12	118.03 (10)	H15—C15—H15"	107.9 (18)
C12—C11—C15	120.97 (10)	H15'—C15—H15"	106.4 (14)
C11—C12—C13	121.25 (10)
C8—N1—C1—C2	179.91 (12)	O1—C6—C7—C2	179.47 (11)
C1—N1—C8—C9	−174.84 (12)	C5—C6—C7—O2	−177.99 (12)
C1—N1—C8—C13	5.77 (19)	C5—C6—C7—C2	1.19 (18)
N1—C1—C2—C3	−179.77 (12)	N1—C8—C9—C10	179.26 (11)
N1—C1—C2—C7	−0.87 (19)	N1—C8—C9—C14	−1.44 (18)
C1—C2—C3—C4	177.46 (12)	C13—C8—C9—C10	−1.34 (18)
C7—C2—C3—C4	−1.44 (19)	C13—C8—C9—C14	177.96 (12)
C1—C2—C7—O2	0.84 (19)	N1—C8—C13—C12	179.40 (12)
C1—C2—C7—C6	−178.32 (11)	C9—C8—C13—C12	0.0 (2)
C3—C2—C7—O2	179.74 (12)	C8—C9—C10—C11	1.45 (19)
C3—C2—C7—C6	0.58 (18)	C14—C9—C10—C11	−177.87 (12)
C2—C3—C4—C5	0.53 (19)	C9—C10—C11—C12	−0.20 (19)
C3—C4—C5—C6	1.26 (19)	C9—C10—C11—C15	177.81 (12)
C4—C5—C6—O1	179.58 (12)	C10—C11—C12—C13	−1.2 (2)
C4—C5—C6—C7	−2.1 (2)	C15—C11—C12—C13	−179.20 (12)
O1—C6—C7—O2	0.29 (18)	C11—C12—C13—C8	1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H21···O2	0.85 (2)	2.340 (17)	2.7674 (12)	111.3 (12)
O1—H21···O2ii	0.85 (2)	2.00 (2)	2.7320 (13)	143.4 (15)
N1—H31···O2	1.00 (2)	1.72 (2)	2.5873 (12)	142.7 (18)
C13—H13···O1v	0.980 (14)	2.557 (14)	3.3069 (14)	133.3 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H21⋯O2	0.85 (2)	2.340 (17)	2.7674 (12)	111.3 (12)
O1—H21⋯O2i	0.85 (2)	2.00 (2)	2.7320 (13)	143.4 (15)
N1—H31⋯O2	1.00 (2)	1.72 (2)	2.5873 (12)	142.7 (18)
C13—H13⋯O1ii	0.980 (14)	2.557 (14)	3.3069 (14)	133.3 (13)

Symmetry codes: (i) ; (ii) .