(3E,5E)-3,5-Bis(naphthalen-1-yl-methyl-idene)piperidin-4-one.

In the title compound, C(27)H(21)NO, the piperidine ring adopts a chair conformation. The mean plane through the piperidine ring makes dihedral angles of 49.27 (5) and 63.07 (5)° with the naphthalene ring systems. In the crystal, mol-ecules are linked into dimers via pairs of inter-molecular C-H⋯O inter-actions, generating ten-membered R(2) (2)(10) ring motifs. C-H⋯π inter-actions further stabilize the crystal structure.

Related literature

For the biological activities of α,β-unsaturated ketones, see: Lee et al. (1971 ▶); Anke et al. (1981 ▶); Khodair et al. (1997 ▶); Murakami et al. (2002 ▶); El-Subbagh et al. (2000 ▶); El-Barbary et al. (1994 ▶); Dimmock et al. (1983 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Basiri et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For experimental preparation, see: Das et al. (2007 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C27H21NO

M = 375.45

Monoclinic,

a = 9.4833 (2) Å

b = 10.0838 (2) Å

c = 20.3885 (4) Å

β = 101.513 (1)°

V = 1910.48 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.28 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.979, T max = 0.992

21618 measured reflections

5644 independent reflections

4138 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.125

S = 1.02

5644 reflections

266 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006307/rz2710sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006307/rz2710Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006307/rz2710Isup3.cml

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

C27H21NO	F(000) = 792
Mr = 375.45	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5698 reflections
a = 9.4833 (2) Å	θ = 2.7–29.9°
b = 10.0838 (2) Å	µ = 0.08 mm−1
c = 20.3885 (4) Å	T = 100 K
β = 101.513 (1)°	Plate, yellow
V = 1910.48 (7) Å3	0.28 × 0.21 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5644 independent reflections
Radiation source: fine-focus sealed tube	4138 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 30.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→8
Tmin = 0.979, Tmax = 0.992	k = −13→14
21618 measured reflections	l = −28→28

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.7137P] where P = (Fo2 + 2Fc2)/3
5644 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.20055 (10)	0.98893 (10)	0.10917 (5)	0.0220 (2)
N1	−0.17776 (13)	0.77264 (12)	0.07711 (6)	0.0221 (3)
C1	−0.17882 (15)	1.32180 (13)	0.12377 (7)	0.0184 (3)
C2	−0.06600 (16)	1.34358 (14)	0.18022 (7)	0.0222 (3)
H2A	0.0171	1.2887	0.1868	0.027*
C3	−0.07534 (17)	1.44260 (15)	0.22535 (8)	0.0274 (3)
H3A	0.0020	1.4567	0.2622	0.033*
C4	−0.19864 (18)	1.52344 (16)	0.21750 (8)	0.0310 (4)
H4A	−0.2053	1.5905	0.2495	0.037*
C5	−0.30899 (17)	1.50529 (15)	0.16367 (8)	0.0274 (3)
H5A	−0.3917	1.5604	0.1586	0.033*
C6	−0.30191 (15)	1.40587 (14)	0.11546 (7)	0.0209 (3)
C7	−0.41645 (16)	1.38733 (14)	0.05993 (7)	0.0233 (3)
H7A	−0.4982	1.4438	0.0544	0.028*
C8	−0.41112 (16)	1.28894 (14)	0.01388 (7)	0.0234 (3)
H8A	−0.4880	1.2785	−0.0235	0.028*
C9	−0.29140 (15)	1.20365 (14)	0.02233 (7)	0.0206 (3)
H9A	−0.2890	1.1357	−0.0097	0.025*
C10	−0.17705 (14)	1.21611 (13)	0.07607 (6)	0.0174 (3)
C11	−0.05484 (15)	1.12471 (13)	0.08701 (6)	0.0181 (3)
H11A	0.0365	1.1635	0.1039	0.022*
C12	−0.05458 (14)	0.99261 (13)	0.07631 (6)	0.0168 (3)
C13	−0.18459 (14)	0.90730 (13)	0.04956 (7)	0.0188 (3)
H13A	−0.2712	0.9519	0.0593	0.023*
H13B	−0.1962	0.9012	0.0003	0.023*
C14	−0.04589 (15)	0.70382 (14)	0.07028 (7)	0.0217 (3)
H14A	−0.0459	0.6913	0.0221	0.026*
H14B	−0.0449	0.6149	0.0909	0.026*
C15	0.08935 (14)	0.77746 (13)	0.10247 (6)	0.0173 (3)
C16	0.08796 (14)	0.92523 (13)	0.09686 (6)	0.0171 (3)
C17	0.20833 (15)	0.72198 (13)	0.13867 (6)	0.0185 (3)
H17A	0.2798	0.7811	0.1613	0.022*
C18	0.23999 (14)	0.57973 (13)	0.14716 (7)	0.0178 (3)
C19	0.21653 (15)	0.49547 (14)	0.09261 (7)	0.0211 (3)
H19A	0.1734	0.5291	0.0498	0.025*
C20	0.25547 (15)	0.36044 (14)	0.09939 (7)	0.0236 (3)
H20A	0.2389	0.3045	0.0611	0.028*
C21	0.31695 (15)	0.30915 (14)	0.16068 (7)	0.0221 (3)
H21A	0.3411	0.2177	0.1648	0.027*
C22	0.34447 (14)	0.39198 (14)	0.21777 (7)	0.0189 (3)
C23	0.41211 (15)	0.34198 (14)	0.28155 (7)	0.0228 (3)
H23A	0.4373	0.2508	0.2862	0.027*
C24	0.44152 (16)	0.42307 (15)	0.33632 (7)	0.0252 (3)
H24A	0.4891	0.3886	0.3783	0.030*
C25	0.40119 (15)	0.55807 (15)	0.33047 (7)	0.0238 (3)
H25A	0.4207	0.6138	0.3688	0.029*
C26	0.33416 (15)	0.60925 (14)	0.26995 (7)	0.0200 (3)
H26A	0.3062	0.6999	0.2670	0.024*
C27	0.30600 (14)	0.52860 (13)	0.21164 (7)	0.0171 (3)
H1N1	−0.1808 (18)	0.7776 (18)	0.1223 (9)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0211 (5)	0.0162 (5)	0.0274 (5)	0.0004 (4)	0.0013 (4)	−0.0002 (4)
N1	0.0224 (6)	0.0159 (6)	0.0273 (6)	0.0011 (5)	0.0037 (5)	0.0041 (5)
C1	0.0233 (7)	0.0136 (6)	0.0194 (6)	0.0007 (5)	0.0072 (5)	0.0015 (5)
C2	0.0239 (7)	0.0189 (7)	0.0244 (7)	0.0014 (6)	0.0064 (5)	−0.0019 (5)
C3	0.0323 (8)	0.0254 (8)	0.0243 (7)	−0.0021 (6)	0.0052 (6)	−0.0050 (6)
C4	0.0409 (9)	0.0239 (8)	0.0301 (8)	0.0032 (7)	0.0116 (7)	−0.0085 (6)
C5	0.0323 (8)	0.0211 (7)	0.0309 (8)	0.0076 (6)	0.0113 (6)	−0.0015 (6)
C6	0.0257 (7)	0.0151 (6)	0.0236 (7)	0.0026 (5)	0.0089 (5)	0.0023 (5)
C7	0.0254 (7)	0.0195 (7)	0.0257 (7)	0.0082 (6)	0.0071 (6)	0.0049 (5)
C8	0.0245 (7)	0.0229 (7)	0.0220 (7)	0.0048 (6)	0.0029 (5)	0.0036 (5)
C9	0.0264 (7)	0.0166 (7)	0.0191 (6)	0.0028 (5)	0.0053 (5)	0.0008 (5)
C10	0.0209 (6)	0.0128 (6)	0.0193 (6)	0.0014 (5)	0.0059 (5)	0.0013 (5)
C11	0.0203 (6)	0.0165 (6)	0.0176 (6)	0.0019 (5)	0.0039 (5)	0.0007 (5)
C12	0.0203 (6)	0.0148 (6)	0.0151 (6)	0.0026 (5)	0.0032 (5)	0.0014 (4)
C13	0.0200 (6)	0.0135 (6)	0.0222 (6)	0.0029 (5)	0.0024 (5)	0.0010 (5)
C14	0.0229 (7)	0.0139 (6)	0.0259 (7)	0.0020 (5)	−0.0010 (5)	0.0002 (5)
C15	0.0205 (6)	0.0128 (6)	0.0186 (6)	0.0016 (5)	0.0036 (5)	0.0000 (5)
C16	0.0216 (6)	0.0138 (6)	0.0155 (6)	0.0026 (5)	0.0028 (5)	−0.0005 (4)
C17	0.0206 (6)	0.0153 (6)	0.0190 (6)	0.0006 (5)	0.0022 (5)	−0.0002 (5)
C18	0.0166 (6)	0.0146 (6)	0.0217 (6)	0.0016 (5)	0.0026 (5)	0.0004 (5)
C19	0.0215 (7)	0.0186 (7)	0.0215 (7)	0.0026 (5)	0.0004 (5)	−0.0006 (5)
C20	0.0215 (7)	0.0184 (7)	0.0294 (7)	0.0016 (6)	0.0013 (6)	−0.0070 (5)
C21	0.0185 (7)	0.0137 (6)	0.0331 (7)	0.0012 (5)	0.0025 (5)	0.0001 (5)
C22	0.0146 (6)	0.0159 (6)	0.0260 (7)	0.0003 (5)	0.0036 (5)	0.0026 (5)
C23	0.0204 (7)	0.0176 (7)	0.0301 (7)	0.0015 (5)	0.0046 (6)	0.0078 (5)
C24	0.0226 (7)	0.0287 (8)	0.0233 (7)	0.0015 (6)	0.0023 (5)	0.0079 (6)
C25	0.0236 (7)	0.0273 (8)	0.0207 (7)	−0.0002 (6)	0.0049 (5)	0.0004 (5)
C26	0.0210 (7)	0.0161 (6)	0.0231 (7)	0.0017 (5)	0.0049 (5)	0.0002 (5)
C27	0.0152 (6)	0.0149 (6)	0.0211 (6)	0.0001 (5)	0.0032 (5)	0.0017 (5)

O1—C16	1.2283 (16)	C13—H13A	0.9900
N1—C14	1.4610 (18)	C13—H13B	0.9900
N1—C13	1.4660 (17)	C14—C15	1.5136 (19)
N1—H1N1	0.928 (18)	C14—H14A	0.9900
C1—C2	1.4235 (19)	C14—H14B	0.9900
C1—C6	1.4251 (19)	C15—C17	1.3411 (18)
C1—C10	1.4451 (18)	C15—C16	1.4943 (18)
C2—C3	1.372 (2)	C17—C18	1.4686 (18)
C2—H2A	0.9500	C17—H17A	0.9500
C3—C4	1.408 (2)	C18—C19	1.3819 (18)
C3—H3A	0.9500	C18—C27	1.4344 (18)
C4—C5	1.369 (2)	C19—C20	1.410 (2)
C4—H4A	0.9500	C19—H19A	0.9500
C5—C6	1.415 (2)	C20—C21	1.371 (2)
C5—H5A	0.9500	C20—H20A	0.9500
C6—C7	1.416 (2)	C21—C22	1.414 (2)
C7—C8	1.374 (2)	C21—H21A	0.9500
C7—H7A	0.9500	C22—C23	1.4226 (19)
C8—C9	1.407 (2)	C22—C27	1.4242 (18)
C8—H8A	0.9500	C23—C24	1.367 (2)
C9—C10	1.3848 (19)	C23—H23A	0.9500
C9—H9A	0.9500	C24—C25	1.413 (2)
C10—C11	1.4626 (18)	C24—H24A	0.9500
C11—C12	1.3499 (18)	C25—C26	1.3711 (19)
C11—H11A	0.9500	C25—H25A	0.9500
C12—C16	1.4961 (18)	C26—C27	1.4210 (19)
C12—C13	1.5130 (18)	C26—H26A	0.9500
C14—N1—C13	112.12 (11)	N1—C14—C15	113.13 (11)
C14—N1—H1N1	108.5 (11)	N1—C14—H14A	109.0
C13—N1—H1N1	108.8 (11)	C15—C14—H14A	109.0
C2—C1—C6	118.03 (12)	N1—C14—H14B	109.0
C2—C1—C10	123.38 (12)	C15—C14—H14B	109.0
C6—C1—C10	118.55 (12)	H14A—C14—H14B	107.8
C3—C2—C1	121.04 (14)	C17—C15—C16	116.85 (12)
C3—C2—H2A	119.5	C17—C15—C14	125.52 (12)
C1—C2—H2A	119.5	C16—C15—C14	117.53 (11)
C2—C3—C4	120.54 (14)	O1—C16—C15	120.79 (12)
C2—C3—H3A	119.7	O1—C16—C12	121.31 (12)
C4—C3—H3A	119.7	C15—C16—C12	117.90 (12)
C5—C4—C3	119.88 (14)	C15—C17—C18	127.02 (12)
C5—C4—H4A	120.1	C15—C17—H17A	116.5
C3—C4—H4A	120.1	C18—C17—H17A	116.5
C4—C5—C6	121.12 (14)	C19—C18—C27	119.17 (12)
C4—C5—H5A	119.4	C19—C18—C17	120.63 (12)
C6—C5—H5A	119.4	C27—C18—C17	120.04 (12)
C5—C6—C7	120.91 (13)	C18—C19—C20	121.18 (13)
C5—C6—C1	119.36 (13)	C18—C19—H19A	119.4
C7—C6—C1	119.72 (13)	C20—C19—H19A	119.4
C8—C7—C6	120.98 (13)	C21—C20—C19	120.60 (13)
C8—C7—H7A	119.5	C21—C20—H20A	119.7
C6—C7—H7A	119.5	C19—C20—H20A	119.7
C7—C8—C9	119.77 (13)	C20—C21—C22	120.18 (13)
C7—C8—H8A	120.1	C20—C21—H21A	119.9
C9—C8—H8A	120.1	C22—C21—H21A	119.9
C10—C9—C8	121.78 (13)	C21—C22—C23	121.24 (13)
C10—C9—H9A	119.1	C21—C22—C27	119.81 (12)
C8—C9—H9A	119.1	C23—C22—C27	118.95 (13)
C9—C10—C1	119.13 (12)	C24—C23—C22	121.06 (13)
C9—C10—C11	122.35 (12)	C24—C23—H23A	119.5
C1—C10—C11	118.51 (12)	C22—C23—H23A	119.5
C12—C11—C10	128.62 (13)	C23—C24—C25	119.99 (13)
C12—C11—H11A	115.7	C23—C24—H24A	120.0
C10—C11—H11A	115.7	C25—C24—H24A	120.0
C11—C12—C16	115.70 (12)	C26—C25—C24	120.51 (14)
C11—C12—C13	126.27 (12)	C26—C25—H25A	119.7
C16—C12—C13	117.94 (11)	C24—C25—H25A	119.7
N1—C13—C12	114.71 (11)	C25—C26—C27	120.90 (13)
N1—C13—H13A	108.6	C25—C26—H26A	119.6
C12—C13—H13A	108.6	C27—C26—H26A	119.6
N1—C13—H13B	108.6	C26—C27—C22	118.56 (12)
C12—C13—H13B	108.6	C26—C27—C18	122.40 (12)
H13A—C13—H13B	107.6	C22—C27—C18	119.04 (12)
C6—C1—C2—C3	0.0 (2)	C14—C15—C16—O1	−164.86 (12)
C10—C1—C2—C3	−177.67 (14)	C17—C15—C16—C12	−161.14 (12)
C1—C2—C3—C4	1.3 (2)	C14—C15—C16—C12	15.56 (17)
C2—C3—C4—C5	−1.4 (2)	C11—C12—C16—O1	−14.65 (19)
C3—C4—C5—C6	0.2 (2)	C13—C12—C16—O1	168.69 (12)
C4—C5—C6—C7	179.89 (15)	C11—C12—C16—C15	164.93 (12)
C4—C5—C6—C1	1.1 (2)	C13—C12—C16—C15	−11.73 (17)
C2—C1—C6—C5	−1.2 (2)	C16—C15—C17—C18	−174.83 (13)
C10—C1—C6—C5	176.59 (13)	C14—C15—C17—C18	8.8 (2)
C2—C1—C6—C7	−179.99 (13)	C15—C17—C18—C19	46.2 (2)
C10—C1—C6—C7	−2.2 (2)	C15—C17—C18—C27	−138.58 (14)
C5—C6—C7—C8	−178.55 (14)	C27—C18—C19—C20	0.4 (2)
C1—C6—C7—C8	0.2 (2)	C17—C18—C19—C20	175.69 (13)
C6—C7—C8—C9	1.0 (2)	C18—C19—C20—C21	0.5 (2)
C7—C8—C9—C10	−0.3 (2)	C19—C20—C21—C22	−1.2 (2)
C8—C9—C10—C1	−1.7 (2)	C20—C21—C22—C23	−178.09 (13)
C8—C9—C10—C11	177.34 (13)	C20—C21—C22—C27	1.0 (2)
C2—C1—C10—C9	−179.42 (13)	C21—C22—C23—C24	178.48 (14)
C6—C1—C10—C9	2.94 (19)	C27—C22—C23—C24	−0.6 (2)
C2—C1—C10—C11	1.5 (2)	C22—C23—C24—C25	1.7 (2)
C6—C1—C10—C11	−176.17 (12)	C23—C24—C25—C26	−0.8 (2)
C9—C10—C11—C12	−37.3 (2)	C24—C25—C26—C27	−1.1 (2)
C1—C10—C11—C12	141.76 (14)	C25—C26—C27—C22	2.1 (2)
C10—C11—C12—C16	−176.09 (12)	C25—C26—C27—C18	−178.11 (13)
C10—C11—C12—C13	0.3 (2)	C21—C22—C27—C26	179.62 (13)
C14—N1—C13—C12	−53.18 (15)	C23—C22—C27—C26	−1.27 (19)
C11—C12—C13—N1	−145.86 (13)	C21—C22—C27—C18	−0.15 (19)
C16—C12—C13—N1	30.42 (17)	C23—C22—C27—C18	178.96 (12)
C13—N1—C14—C15	56.73 (15)	C19—C18—C27—C26	179.70 (13)
N1—C14—C15—C17	138.38 (14)	C17—C18—C27—C26	4.4 (2)
N1—C14—C15—C16	−38.00 (17)	C19—C18—C27—C22	−0.54 (19)
C17—C15—C16—O1	18.44 (19)	C17—C18—C27—C22	−175.85 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O1i	0.99	2.48	3.3758 (17)	150
C26—H26A···Cg1ii	0.95	2.92	3.7532 (15)	147
C25—H25A···Cg2ii	0.95	2.70	3.4923 (16)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O1i	0.99	2.48	3.3758 (17)	150
C26—H26A⋯Cg1ii	0.95	2.92	3.7532 (15)	147
C25—H25A⋯Cg2ii	0.95	2.70	3.4923 (16)	141

Symmetry codes: (i) ; (ii) .