3-Anilino-5,5-di-methyl-cyclo-hex-2-enone.

In the title mol-ecule, C14H17NO, the 5,5-di-methyl-cyclo-hex-2-enone moiety is attached to an aniline group, the dihedral angle subtended [54.43 (3)°] indicating a significant twist. The hexaneone ring has a half-chair conformation with the C atom bearing two methyl groups lying 0.6384 (8) Å above the plane of the five remaining atoms (r.m.s. deviation = 0.0107 Å). The crystal packing can be described as alternating layers parallel to (-101), which are consolidated by N-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Related literature

For the synthesis of the title compound, see: Amini et al. (2013 ▶); Machacek et al. (2002 ▶). For its reactivity, see: Wang et al. (2007 ▶); Mohammadizadeh et al. (2009 ▶); Gao et al. (2008 ▶). For our previous work [inspired by Assy (1996 ▶)] on the preparation and the reactivity of imidazole derivatives, see: Zama et al. (2013a ▶,b ▶); Chelghoum et al. (2011 ▶); Bahnous et al. (2012 ▶) For enamine derivatives as precursors in the synthesis ofcompounds of pharmaceutical inter­est, see: Palko et al. (2008 ▶) Park & Jahng (1998 ▶); Tadesse et al. (1999 ▶); Thummel & Jahng (1985 ▶); When enamines are treated with alkyl halides, an alkyl­ation occurs to give an iminium salt, see: Adams (2000 ▶); Kempf et al. (2003 ▶).

Experimental

Crystal data

C14H17NO

M = 215.29

Monoclinic,

a = 10.1766 (19) Å

b = 13.159 (2) Å

c = 9.2877 (17) Å

β = 104.062 (7)°

V = 1206.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 150 K

0.15 × 0.12 × 0.09 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.667, T max = 0.747

12403 measured reflections

5021 independent reflections

3873 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.04

5021 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681400186X/bq2392sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400186X/bq2392Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681400186X/bq2392Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H17NO	F(000) = 464
Mr = 215.29	Dx = 1.185 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4703 reflections
a = 10.1766 (19) Å	θ = 2.6–34.3°
b = 13.159 (2) Å	µ = 0.07 mm−1
c = 9.2877 (17) Å	T = 150 K
β = 104.062 (7)°	Prism, colorless
V = 1206.5 (4) Å3	0.15 × 0.12 × 0.09 mm
Z = 4

Bruker APEXII diffractometer	3873 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
CCD rotation images, thin slices scans	θmax = 34.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −16→14
Tmin = 0.667, Tmax = 0.747	k = −13→20
12403 measured reflections	l = −12→14
5021 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0725P)2 + 0.1791P] where P = (Fo2 + 2Fc2)/3
5021 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.64385 (8)	0.73838 (6)	0.82567 (9)	0.01988 (15)
C2	0.53143 (8)	0.78529 (6)	0.72449 (9)	0.01973 (15)
H2	0.4742	0.7455	0.6531	0.024*
C3	0.50602 (8)	0.88768 (6)	0.73022 (9)	0.01767 (14)
C4	0.59803 (8)	0.95491 (6)	0.84239 (10)	0.02194 (16)
H4A	0.5593	0.963	0.9274	0.026*
H4B	0.6012	1.0216	0.7987	0.026*
C5	0.74309 (8)	0.91494 (6)	0.89647 (9)	0.01943 (15)
C6	0.73478 (9)	0.80376 (6)	0.94261 (9)	0.02232 (16)
H6A	0.8253	0.775	0.9661	0.027*
H6B	0.7019	0.8017	1.0322	0.027*
C7	0.81684 (10)	0.97776 (8)	1.03068 (11)	0.0320 (2)
H7A	0.7703	0.9715	1.1086	0.048*
H7B	0.8185	1.0478	1.0024	0.048*
H7C	0.908	0.9533	1.0652	0.048*
C8	0.81959 (9)	0.92285 (7)	0.77337 (10)	0.02490 (17)
H8A	0.8268	0.9929	0.7477	0.037*
H8B	0.7712	0.886	0.6876	0.037*
H8C	0.9086	0.8945	0.8079	0.037*
C10	0.29024 (8)	0.89121 (6)	0.53767 (9)	0.01887 (15)
C11	0.15721 (8)	0.90959 (7)	0.54586 (10)	0.02316 (16)
H11	0.1403	0.95	0.6215	0.028*
C12	0.04984 (9)	0.86746 (7)	0.44081 (12)	0.0306 (2)
H12	−0.0388	0.88	0.4461	0.037*
C13	0.07470 (11)	0.80686 (7)	0.32830 (13)	0.0351 (2)
H13	0.003	0.7781	0.2587	0.042*
C14	0.20729 (11)	0.78931 (8)	0.31997 (12)	0.0343 (2)
H14	0.2239	0.7488	0.2443	0.041*
C15	0.31524 (9)	0.83168 (7)	0.42365 (10)	0.02586 (18)
H15	0.4037	0.8203	0.4168	0.031*
N1	0.39813 (7)	0.93664 (5)	0.64459 (8)	0.02126 (14)
H1	0.3945	1.0014	0.6559	0.026*
O1	0.66676 (7)	0.64544 (5)	0.82303 (9)	0.03086 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0190 (3)	0.0142 (3)	0.0280 (4)	−0.0002 (2)	0.0086 (3)	0.0044 (3)
C2	0.0182 (3)	0.0134 (3)	0.0268 (4)	−0.0001 (2)	0.0040 (3)	−0.0003 (3)
C3	0.0170 (3)	0.0144 (3)	0.0217 (3)	0.0010 (2)	0.0048 (3)	−0.0012 (2)
C4	0.0214 (3)	0.0170 (3)	0.0261 (4)	0.0017 (3)	0.0032 (3)	−0.0060 (3)
C5	0.0198 (3)	0.0172 (3)	0.0202 (3)	−0.0011 (3)	0.0027 (3)	−0.0009 (3)
C6	0.0225 (3)	0.0210 (4)	0.0226 (3)	0.0010 (3)	0.0036 (3)	0.0053 (3)
C7	0.0320 (4)	0.0310 (5)	0.0280 (4)	−0.0039 (4)	−0.0024 (4)	−0.0070 (4)
C8	0.0245 (4)	0.0214 (4)	0.0300 (4)	−0.0041 (3)	0.0092 (3)	0.0014 (3)
C10	0.0191 (3)	0.0144 (3)	0.0221 (3)	0.0013 (2)	0.0031 (3)	0.0013 (2)
C11	0.0212 (3)	0.0206 (3)	0.0278 (4)	0.0043 (3)	0.0061 (3)	0.0046 (3)
C12	0.0201 (4)	0.0254 (4)	0.0437 (5)	−0.0011 (3)	0.0025 (3)	0.0103 (4)
C13	0.0317 (5)	0.0228 (4)	0.0420 (5)	−0.0068 (3)	−0.0080 (4)	0.0015 (4)
C14	0.0397 (5)	0.0256 (4)	0.0328 (5)	0.0008 (4)	−0.0004 (4)	−0.0097 (4)
C15	0.0254 (4)	0.0237 (4)	0.0278 (4)	0.0026 (3)	0.0052 (3)	−0.0053 (3)
N1	0.0210 (3)	0.0135 (3)	0.0266 (3)	0.0034 (2)	0.0007 (3)	−0.0026 (2)
O1	0.0290 (3)	0.0135 (3)	0.0487 (4)	0.0018 (2)	0.0067 (3)	0.0065 (3)

C1—O1	1.2463 (10)	C7—H7C	0.96
C1—C2	1.4320 (11)	C8—H8A	0.96
C1—C6	1.5126 (12)	C8—H8B	0.96
C2—C3	1.3754 (11)	C8—H8C	0.96
C2—H2	0.93	C10—C15	1.3895 (12)
C3—N1	1.3523 (10)	C10—C11	1.3954 (12)
C3—C4	1.5069 (11)	C10—N1	1.4209 (10)
C4—C5	1.5323 (12)	C11—C12	1.3911 (13)
C4—H4A	0.97	C11—H11	0.93
C4—H4B	0.97	C12—C13	1.3857 (16)
C5—C7	1.5316 (12)	C12—H12	0.93
C5—C6	1.5326 (12)	C13—C14	1.3895 (16)
C5—C8	1.5351 (12)	C13—H13	0.93
C6—H6A	0.97	C14—C15	1.3896 (13)
C6—H6B	0.97	C14—H14	0.93
C7—H7A	0.96	C15—H15	0.93
C7—H7B	0.96	N1—H1	0.86
O1—C1—C2	122.25 (8)	C5—C7—H7C	109.5
O1—C1—C6	119.18 (7)	H7A—C7—H7C	109.5
C2—C1—C6	118.54 (7)	H7B—C7—H7C	109.5
C3—C2—C1	121.65 (7)	C5—C8—H8A	109.5
C3—C2—H2	119.2	C5—C8—H8B	109.5
C1—C2—H2	119.2	H8A—C8—H8B	109.5
N1—C3—C2	125.26 (7)	C5—C8—H8C	109.5
N1—C3—C4	113.97 (7)	H8A—C8—H8C	109.5
C2—C3—C4	120.72 (7)	H8B—C8—H8C	109.5
C3—C4—C5	114.36 (7)	C15—C10—C11	119.93 (8)
C3—C4—H4A	108.7	C15—C10—N1	121.09 (7)
C5—C4—H4A	108.7	C11—C10—N1	118.95 (8)
C3—C4—H4B	108.7	C12—C11—C10	119.99 (9)
C5—C4—H4B	108.7	C12—C11—H11	120
H4A—C4—H4B	107.6	C10—C11—H11	120
C7—C5—C4	108.91 (7)	C13—C12—C11	120.13 (9)
C7—C5—C6	109.70 (7)	C13—C12—H12	119.9
C4—C5—C6	107.77 (7)	C11—C12—H12	119.9
C7—C5—C8	109.43 (7)	C12—C13—C14	119.69 (9)
C4—C5—C8	110.80 (7)	C12—C13—H13	120.2
C6—C5—C8	110.20 (7)	C14—C13—H13	120.2
C1—C6—C5	114.07 (7)	C13—C14—C15	120.64 (10)
C1—C6—H6A	108.7	C13—C14—H14	119.7
C5—C6—H6A	108.7	C15—C14—H14	119.7
C1—C6—H6B	108.7	C10—C15—C14	119.61 (9)
C5—C6—H6B	108.7	C10—C15—H15	120.2
H6A—C6—H6B	107.6	C14—C15—H15	120.2
C5—C7—H7A	109.5	C3—N1—C10	126.13 (7)
C5—C7—H7B	109.5	C3—N1—H1	116.9
H7A—C7—H7B	109.5	C10—N1—H1	116.9
O1—C1—C2—C3	178.90 (8)	C8—C5—C6—C1	−69.18 (9)
C6—C1—C2—C3	0.93 (12)	C15—C10—C11—C12	0.66 (12)
C1—C2—C3—N1	−176.05 (8)	N1—C10—C11—C12	178.82 (7)
C1—C2—C3—C4	1.17 (12)	C10—C11—C12—C13	0.27 (13)
N1—C3—C4—C5	−157.43 (7)	C11—C12—C13—C14	−0.70 (15)
C2—C3—C4—C5	25.06 (11)	C12—C13—C14—C15	0.19 (16)
C3—C4—C5—C7	−168.72 (7)	C11—C10—C15—C14	−1.17 (13)
C3—C4—C5—C6	−49.78 (9)	N1—C10—C15—C14	−179.28 (8)
C3—C4—C5—C8	70.86 (9)	C13—C14—C15—C10	0.74 (15)
O1—C1—C6—C5	152.80 (8)	C2—C3—N1—C10	2.19 (14)
C2—C1—C6—C5	−29.16 (11)	C4—C3—N1—C10	−175.20 (7)
C7—C5—C6—C1	170.28 (7)	C15—C10—N1—C3	−54.91 (12)
C4—C5—C6—C1	51.84 (9)	C11—C10—N1—C3	126.96 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.8587 (11)	165
C8—H8A···Cg1ii	0.96	2.61	3.5547 (12)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.02	2.8587 (11)	165
C8—H8A⋯Cg1ii	0.96	2.61	3.5547 (12)	157

Symmetry codes: (i) ; (ii) .