(E)-2-[4-(Piperidin-1-yl)benzyl-idene]-2,3-dihydro-1H-inden-1-one.

In the title compound, C(21)H(21)NO, the indene ring system is essentially planar with a maximum deviation of 0.066 (1) Å and makes dihedral angles of 7.93 (6) and 2.43 (6)°, respectively, with the benzene plane and the mean plane of the piperidine ring. These latter two planes make a dihedral angle of 7.61 (7)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming infinite chains along the b axis.

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶). For background to prostate cancer, see: Heidenreich et al. (2008 ▶); Syed et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H21NO

M = 303.39

Orthorhombic,

a = 31.587 (5) Å

b = 6.3168 (10) Å

c = 7.8396 (12) Å

V = 1564.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.48 × 0.44 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.993

9828 measured reflections

2764 independent reflections

2563 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

2764 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 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 datablocks global, I. DOI: 10.1107/S1600536810041723/is2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041723/is2615Isup2.hkl

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

C21H21NO	F(000) = 648
Mr = 303.39	Dx = 1.288 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3558 reflections
a = 31.587 (5) Å	θ = 2.9–31.5°
b = 6.3168 (10) Å	µ = 0.08 mm−1
c = 7.8396 (12) Å	T = 100 K
V = 1564.2 (4) Å3	Plate, yellow
Z = 4	0.48 × 0.44 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	2764 independent reflections
Radiation source: fine-focus sealed tube	2563 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 31.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −40→46
Tmin = 0.963, Tmax = 0.993	k = −9→9
9828 measured reflections	l = −11→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.0999P] where P = (Fo2 + 2Fc2)/3
2764 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

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

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.17945 (3)	1.37433 (17)	0.61883 (16)	0.0241 (2)
N1	0.04981 (4)	0.63258 (19)	0.61569 (17)	0.0179 (2)
C1	−0.18171 (4)	1.1957 (2)	0.55722 (18)	0.0184 (3)
C2	−0.22001 (4)	1.0902 (2)	0.48828 (18)	0.0179 (3)
C3	−0.26187 (5)	1.1607 (3)	0.4895 (2)	0.0218 (3)
H3A	−0.2689	1.2932	0.5326	0.026*
C4	−0.29267 (5)	1.0262 (3)	0.4242 (2)	0.0241 (3)
H4A	−0.3209	1.0680	0.4255	0.029*
C5	−0.28173 (5)	0.8288 (3)	0.3566 (2)	0.0231 (3)
H5A	−0.3028	0.7425	0.3112	0.028*
C6	−0.23996 (4)	0.7590 (3)	0.3560 (2)	0.0217 (3)
H6A	−0.2329	0.6274	0.3112	0.026*
C7	−0.20910 (4)	0.8912 (2)	0.42409 (19)	0.0184 (3)
C8	−0.16237 (5)	0.8473 (2)	0.4457 (2)	0.0200 (3)
H8A	−0.1578	0.7202	0.5126	0.024*
H8B	−0.1486	0.8312	0.3360	0.024*
C9	−0.14622 (4)	1.0408 (2)	0.53840 (18)	0.0176 (3)
C10	−0.10770 (4)	1.0829 (2)	0.60425 (19)	0.0186 (3)
H10A	−0.1055	1.2137	0.6579	0.022*
C11	−0.06892 (4)	0.9572 (2)	0.60519 (18)	0.0175 (3)
C12	−0.06350 (5)	0.7587 (2)	0.52658 (19)	0.0196 (3)
H12A	−0.0865	0.6964	0.4721	0.023*
C13	−0.02498 (5)	0.6529 (2)	0.52761 (19)	0.0191 (3)
H13A	−0.0227	0.5234	0.4719	0.023*
C14	0.01083 (4)	0.7381 (2)	0.61163 (17)	0.0169 (2)
C15	0.00507 (5)	0.9344 (2)	0.6943 (2)	0.0228 (3)
H15A	0.0276	0.9948	0.7534	0.027*
C16	−0.03344 (4)	1.0388 (3)	0.6890 (2)	0.0224 (3)
H16A	−0.0358	1.1690	0.7435	0.027*
C17	0.05603 (5)	0.4579 (2)	0.4944 (2)	0.0214 (3)
H17A	0.0575	0.5149	0.3797	0.026*
H17B	0.0318	0.3635	0.5000	0.026*
C18	0.09625 (5)	0.3320 (2)	0.5307 (2)	0.0219 (3)
H18A	0.0927	0.2543	0.6364	0.026*
H18B	0.1006	0.2299	0.4399	0.026*
C19	0.13536 (5)	0.4725 (2)	0.5447 (2)	0.0226 (3)
H19A	0.1598	0.3880	0.5759	0.027*
H19B	0.1411	0.5397	0.4358	0.027*
C20	0.12720 (5)	0.6394 (2)	0.6797 (2)	0.0198 (3)
H20A	0.1514	0.7338	0.6864	0.024*
H20B	0.1239	0.5714	0.7899	0.024*
C21	0.08766 (5)	0.7671 (2)	0.6395 (2)	0.0203 (3)
H21A	0.0824	0.8659	0.7318	0.024*
H21B	0.0925	0.8487	0.5365	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0280 (5)	0.0152 (5)	0.0289 (5)	0.0000 (4)	0.0002 (5)	−0.0022 (4)
N1	0.0192 (5)	0.0134 (5)	0.0211 (5)	−0.0015 (4)	−0.0024 (4)	−0.0024 (5)
C1	0.0204 (6)	0.0165 (6)	0.0182 (6)	−0.0006 (5)	0.0019 (5)	0.0018 (5)
C2	0.0190 (6)	0.0168 (6)	0.0179 (5)	−0.0003 (5)	0.0008 (5)	0.0010 (5)
C3	0.0215 (7)	0.0227 (7)	0.0213 (6)	0.0037 (5)	0.0003 (5)	0.0011 (6)
C4	0.0196 (6)	0.0317 (8)	0.0210 (6)	0.0000 (6)	−0.0004 (5)	0.0035 (7)
C5	0.0218 (7)	0.0283 (8)	0.0190 (6)	−0.0054 (6)	−0.0012 (5)	0.0015 (6)
C6	0.0234 (7)	0.0204 (7)	0.0212 (6)	−0.0042 (5)	0.0000 (5)	−0.0010 (6)
C7	0.0188 (6)	0.0189 (6)	0.0174 (6)	−0.0017 (5)	0.0009 (5)	0.0004 (5)
C8	0.0195 (6)	0.0171 (6)	0.0232 (6)	0.0008 (5)	0.0014 (5)	−0.0032 (5)
C9	0.0199 (6)	0.0148 (6)	0.0182 (6)	−0.0001 (5)	0.0024 (5)	0.0001 (5)
C10	0.0215 (6)	0.0165 (6)	0.0178 (6)	−0.0010 (5)	0.0018 (5)	−0.0015 (6)
C11	0.0193 (6)	0.0169 (6)	0.0163 (5)	−0.0014 (5)	0.0010 (5)	−0.0001 (5)
C12	0.0200 (6)	0.0178 (6)	0.0209 (6)	−0.0036 (5)	−0.0023 (5)	−0.0025 (5)
C13	0.0226 (6)	0.0139 (6)	0.0209 (6)	−0.0019 (5)	−0.0024 (5)	−0.0024 (5)
C14	0.0197 (6)	0.0150 (6)	0.0160 (6)	−0.0012 (5)	−0.0009 (5)	0.0004 (5)
C15	0.0203 (6)	0.0199 (6)	0.0283 (7)	−0.0004 (6)	−0.0039 (6)	−0.0079 (6)
C16	0.0210 (6)	0.0213 (7)	0.0249 (6)	0.0003 (6)	−0.0001 (6)	−0.0084 (6)
C17	0.0271 (7)	0.0149 (6)	0.0222 (6)	0.0024 (5)	−0.0059 (5)	−0.0035 (5)
C18	0.0279 (7)	0.0149 (6)	0.0230 (6)	0.0037 (5)	−0.0028 (6)	−0.0016 (6)
C19	0.0252 (7)	0.0197 (7)	0.0229 (6)	0.0033 (6)	0.0022 (5)	−0.0006 (6)
C20	0.0199 (6)	0.0173 (6)	0.0222 (6)	−0.0005 (5)	−0.0003 (5)	−0.0008 (5)
C21	0.0197 (6)	0.0147 (6)	0.0265 (7)	−0.0023 (5)	−0.0025 (5)	−0.0017 (5)

O1—C1	1.2297 (18)	C11—C12	1.407 (2)
N1—C14	1.4004 (17)	C12—C13	1.388 (2)
N1—C17	1.4697 (19)	C12—H12A	0.9300
N1—C21	1.4785 (17)	C13—C14	1.4151 (18)
C1—C2	1.483 (2)	C13—H13A	0.9300
C1—C9	1.4951 (19)	C14—C15	1.411 (2)
C2—C3	1.395 (2)	C15—C16	1.384 (2)
C2—C7	1.397 (2)	C15—H15A	0.9300
C3—C4	1.389 (2)	C16—H16A	0.9300
C3—H3A	0.9300	C17—C18	1.525 (2)
C4—C5	1.399 (2)	C17—H17A	0.9700
C4—H4A	0.9300	C17—H17B	0.9700
C5—C6	1.391 (2)	C18—C19	1.525 (2)
C5—H5A	0.9300	C18—H18A	0.9700
C6—C7	1.390 (2)	C18—H18B	0.9700
C6—H6A	0.9300	C19—C20	1.516 (2)
C7—C8	1.512 (2)	C19—H19A	0.9700
C8—C9	1.511 (2)	C19—H19B	0.9700
C8—H8A	0.9700	C20—C21	1.520 (2)
C8—H8B	0.9700	C20—H20A	0.9700
C9—C10	1.3482 (19)	C20—H20B	0.9700
C10—C11	1.4601 (19)	C21—H21A	0.9700
C10—H10A	0.9300	C21—H21B	0.9700
C11—C16	1.3977 (19)
C14—N1—C17	117.39 (12)	C12—C13—C14	121.35 (13)
C14—N1—C21	116.13 (11)	C12—C13—H13A	119.3
C17—N1—C21	113.90 (12)	C14—C13—H13A	119.3
O1—C1—C2	127.06 (13)	N1—C14—C15	121.40 (12)
O1—C1—C9	126.56 (13)	N1—C14—C13	122.18 (12)
C2—C1—C9	106.38 (12)	C15—C14—C13	116.41 (12)
C3—C2—C7	121.54 (14)	C16—C15—C14	121.22 (13)
C3—C2—C1	128.86 (14)	C16—C15—H15A	119.4
C7—C2—C1	109.53 (12)	C14—C15—H15A	119.4
C4—C3—C2	117.79 (14)	C15—C16—C11	122.87 (14)
C4—C3—H3A	121.1	C15—C16—H16A	118.6
C2—C3—H3A	121.1	C11—C16—H16A	118.6
C3—C4—C5	120.79 (14)	N1—C17—C18	112.47 (12)
C3—C4—H4A	119.6	N1—C17—H17A	109.1
C5—C4—H4A	119.6	C18—C17—H17A	109.1
C6—C5—C4	121.20 (14)	N1—C17—H17B	109.1
C6—C5—H5A	119.4	C18—C17—H17B	109.1
C4—C5—H5A	119.4	H17A—C17—H17B	107.8
C7—C6—C5	118.27 (14)	C19—C18—C17	112.63 (12)
C7—C6—H6A	120.9	C19—C18—H18A	109.1
C5—C6—H6A	120.9	C17—C18—H18A	109.1
C6—C7—C2	120.39 (14)	C19—C18—H18B	109.1
C6—C7—C8	128.13 (14)	C17—C18—H18B	109.1
C2—C7—C8	111.45 (13)	H18A—C18—H18B	107.8
C9—C8—C7	103.59 (12)	C20—C19—C18	108.49 (12)
C9—C8—H8A	111.0	C20—C19—H19A	110.0
C7—C8—H8A	111.0	C18—C19—H19A	110.0
C9—C8—H8B	111.0	C20—C19—H19B	110.0
C7—C8—H8B	111.0	C18—C19—H19B	110.0
H8A—C8—H8B	109.0	H19A—C19—H19B	108.4
C10—C9—C1	120.65 (13)	C19—C20—C21	111.33 (12)
C10—C9—C8	130.43 (13)	C19—C20—H20A	109.4
C1—C9—C8	108.88 (12)	C21—C20—H20A	109.4
C9—C10—C11	130.66 (13)	C19—C20—H20B	109.4
C9—C10—H10A	114.7	C21—C20—H20B	109.4
C11—C10—H10A	114.7	H20A—C20—H20B	108.0
C16—C11—C12	115.92 (13)	N1—C21—C20	112.69 (11)
C16—C11—C10	118.30 (13)	N1—C21—H21A	109.1
C12—C11—C10	125.77 (13)	C20—C21—H21A	109.1
C13—C12—C11	122.20 (13)	N1—C21—H21B	109.1
C13—C12—H12A	118.9	C20—C21—H21B	109.1
C11—C12—H12A	118.9	H21A—C21—H21B	107.8
O1—C1—C2—C3	−5.5 (3)	C9—C10—C11—C16	−177.96 (16)
C9—C1—C2—C3	174.07 (14)	C9—C10—C11—C12	2.9 (3)
O1—C1—C2—C7	177.72 (15)	C16—C11—C12—C13	−1.8 (2)
C9—C1—C2—C7	−2.73 (16)	C10—C11—C12—C13	177.35 (14)
C7—C2—C3—C4	−0.1 (2)	C11—C12—C13—C14	1.4 (2)
C1—C2—C3—C4	−176.58 (15)	C17—N1—C14—C15	−165.73 (14)
C2—C3—C4—C5	−1.2 (2)	C21—N1—C14—C15	−26.1 (2)
C3—C4—C5—C6	1.4 (2)	C17—N1—C14—C13	15.4 (2)
C4—C5—C6—C7	−0.2 (2)	C21—N1—C14—C13	155.05 (13)
C5—C6—C7—C2	−1.1 (2)	C12—C13—C14—N1	179.27 (13)
C5—C6—C7—C8	176.75 (15)	C12—C13—C14—C15	0.3 (2)
C3—C2—C7—C6	1.3 (2)	N1—C14—C15—C16	179.56 (14)
C1—C2—C7—C6	178.40 (13)	C13—C14—C15—C16	−1.5 (2)
C3—C2—C7—C8	−176.88 (14)	C14—C15—C16—C11	1.0 (3)
C1—C2—C7—C8	0.19 (17)	C12—C11—C16—C15	0.6 (2)
C6—C7—C8—C9	−175.67 (15)	C10—C11—C16—C15	−178.60 (15)
C2—C7—C8—C9	2.37 (16)	C14—N1—C17—C18	−170.28 (13)
O1—C1—C9—C10	5.7 (2)	C21—N1—C17—C18	49.17 (17)
C2—C1—C9—C10	−173.86 (13)	N1—C17—C18—C19	−52.23 (18)
O1—C1—C9—C8	−176.22 (15)	C17—C18—C19—C20	55.49 (17)
C2—C1—C9—C8	4.22 (15)	C18—C19—C20—C21	−56.53 (16)
C7—C8—C9—C10	173.83 (15)	C14—N1—C21—C20	167.89 (13)
C7—C8—C9—C1	−4.00 (15)	C17—N1—C21—C20	−51.05 (17)
C1—C9—C10—C11	178.71 (14)	C19—C20—C21—N1	55.19 (17)
C8—C9—C10—C11	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.44	3.3256 (18)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.44	3.3256 (18)	152

Symmetry code: (i) .