N-Cyclo-pentyl-N-(3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide.

The title mol-ecule, C(16)H(19)NO(2), consists of an indane moiety, which is connected through an N atom to an acetamide group and a cyclo-pentane ring. The N atom adopts planar triangular geometry. Inter-molecular inter-actions, such as π-π stacking or hydrogen bonding, were not observed.

Related literature

For background information on the indane pharmacophore, see: Vaccva et al. (1994 ▶); Buckle et al. (1973 ▶); Heinzelmann et al. (1940 ▶). For details of the pharmacological activity of the title compound, see: Sheridan et al. (1990 ▶, 1999a ▶,b ▶, 2008 ▶); Frankish et al. (2004 ▶). For ionization characteristics, see: Simplício et al. (2004 ▶).

Experimental

Crystal data

C16H19NO2

M = 257.32

Triclinic,

a = 8.1539 (16) Å

b = 8.9944 (18) Å

c = 10.084 (2) Å

α = 87.97 (3)°

β = 81.29 (3)°

γ = 63.15 (3)°

V = 651.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.60 × 0.50 × 0.30 mm

Data collection

Rigaku Saturn 724 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2006 ▶) T min = 0.726, T max = 1.000

7260 measured reflections

2191 independent reflections

2157 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.100

S = 1.13

2191 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681200606X/hg5169sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200606X/hg5169Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200606X/hg5169Isup3.cml

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

C16H19NO2	Z = 2
Mr = 257.32	F(000) = 276
Triclinic, P1	Dx = 1.311 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1539 (16) Å	Cell parameters from 2546 reflections
b = 8.9944 (18) Å	θ = 2.0–31.2°
c = 10.084 (2) Å	µ = 0.09 mm−1
α = 87.97 (3)°	T = 150 K
β = 81.29 (3)°	Prism, colourless
γ = 63.15 (3)°	0.60 × 0.50 × 0.30 mm
V = 651.8 (2) Å3

Rigaku Saturn 724 diffractometer	2191 independent reflections
Radiation source: fine-focus sealed tube	2157 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 2.8°
ω and phi scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2006)	k = −10→8
Tmin = 0.726, Tmax = 1.000	l = −11→11
7260 measured 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.3106P] where P = (Fo2 + 2Fc2)/3
2191 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The su's on the Cell Angles were measured.

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
O2	0.31603 (15)	0.52993 (14)	0.35282 (11)	0.0247 (3)
N1	0.26193 (16)	0.31399 (15)	0.30730 (12)	0.0180 (3)
C12	0.3026 (2)	0.13741 (18)	0.31299 (14)	0.0178 (3)
H12	0.4075	0.0812	0.3627	0.021*
C5	0.15437 (19)	0.51234 (18)	0.12014 (14)	0.0178 (3)
C9	0.10493 (19)	0.42530 (18)	0.24012 (14)	0.0182 (3)
H9	0.0535	0.3566	0.2071	0.022*
C6	0.0277 (2)	0.67950 (19)	0.12237 (14)	0.0188 (3)
C10	0.3582 (2)	0.38022 (19)	0.36131 (14)	0.0191 (3)
C4	0.2976 (2)	0.4435 (2)	0.01256 (15)	0.0221 (3)
H4	0.3821	0.3311	0.0095	0.027*
C7	−0.1091 (2)	0.72363 (19)	0.24640 (15)	0.0199 (3)
C11	0.5168 (2)	0.2668 (2)	0.43334 (16)	0.0245 (4)
H11A	0.5711	0.3301	0.4669	0.037*
H11B	0.6092	0.1799	0.3720	0.037*
H11C	0.4709	0.2182	0.5069	0.037*
C1	0.0406 (2)	0.7826 (2)	0.01944 (15)	0.0226 (3)
H1	−0.0454	0.8945	0.0219	0.027*
C16	0.1404 (2)	0.10622 (19)	0.38594 (15)	0.0222 (3)
H16A	0.1517	0.0863	0.4801	0.027*
H16B	0.0218	0.2016	0.3793	0.027*
C13	0.3576 (2)	0.04558 (19)	0.17613 (14)	0.0205 (3)
H13A	0.2763	0.1118	0.1132	0.025*
H13B	0.4852	0.0175	0.1386	0.025*
C3	0.3120 (2)	0.5459 (2)	−0.09033 (15)	0.0245 (4)
H3	0.4079	0.5014	−0.1624	0.029*
C14	0.3337 (2)	−0.11046 (19)	0.21048 (15)	0.0227 (3)
H14A	0.4397	−0.1927	0.2482	0.027*
H14B	0.3200	−0.1595	0.1313	0.027*
C2	0.1849 (2)	0.7143 (2)	−0.08713 (15)	0.0251 (4)
H2	0.1969	0.7811	−0.1566	0.030*
C8	−0.0572 (2)	0.56929 (19)	0.32894 (15)	0.0223 (3)
H8A	−0.1624	0.5451	0.3517	0.027*
H8B	−0.0181	0.5849	0.4113	0.027*
C15	0.1556 (2)	−0.04907 (19)	0.31440 (16)	0.0242 (4)
H15A	0.1640	−0.1346	0.3782	0.029*
H15B	0.0478	−0.0206	0.2704	0.029*
O1	−0.24001 (15)	0.85977 (14)	0.27869 (11)	0.0280 (3)

	U11	U22	U33	U12	U13	U23
O2	0.0310 (6)	0.0181 (7)	0.0266 (6)	−0.0122 (5)	−0.0055 (5)	0.0010 (4)
N1	0.0186 (6)	0.0145 (7)	0.0187 (6)	−0.0058 (5)	−0.0023 (5)	0.0003 (5)
C12	0.0196 (7)	0.0130 (8)	0.0187 (7)	−0.0058 (6)	−0.0016 (6)	0.0001 (6)
C5	0.0174 (7)	0.0187 (8)	0.0181 (7)	−0.0083 (6)	−0.0052 (5)	0.0009 (6)
C9	0.0168 (7)	0.0159 (8)	0.0192 (7)	−0.0055 (6)	−0.0011 (5)	−0.0003 (6)
C6	0.0187 (7)	0.0180 (8)	0.0213 (7)	−0.0083 (6)	−0.0072 (6)	0.0007 (6)
C10	0.0206 (7)	0.0199 (9)	0.0154 (7)	−0.0089 (6)	0.0008 (5)	−0.0016 (6)
C4	0.0209 (7)	0.0201 (9)	0.0225 (8)	−0.0071 (6)	−0.0021 (6)	−0.0006 (6)
C7	0.0164 (7)	0.0190 (9)	0.0235 (8)	−0.0063 (6)	−0.0054 (6)	−0.0029 (6)
C11	0.0248 (8)	0.0229 (9)	0.0271 (8)	−0.0108 (7)	−0.0072 (6)	−0.0002 (6)
C1	0.0235 (8)	0.0192 (8)	0.0266 (8)	−0.0096 (6)	−0.0092 (6)	0.0030 (6)
C16	0.0236 (8)	0.0196 (9)	0.0212 (7)	−0.0092 (7)	0.0017 (6)	−0.0008 (6)
C13	0.0188 (7)	0.0199 (9)	0.0192 (7)	−0.0061 (6)	−0.0007 (6)	−0.0021 (6)
C3	0.0239 (8)	0.0313 (10)	0.0192 (8)	−0.0136 (7)	−0.0019 (6)	0.0000 (6)
C14	0.0220 (8)	0.0186 (9)	0.0255 (8)	−0.0071 (7)	−0.0032 (6)	−0.0044 (6)
C2	0.0306 (8)	0.0299 (10)	0.0211 (8)	−0.0181 (8)	−0.0091 (6)	0.0079 (6)
C8	0.0189 (7)	0.0206 (9)	0.0218 (8)	−0.0051 (6)	0.0008 (6)	−0.0015 (6)
C15	0.0235 (8)	0.0183 (9)	0.0304 (8)	−0.0098 (7)	−0.0010 (6)	−0.0012 (6)
O1	0.0219 (6)	0.0211 (7)	0.0327 (6)	−0.0026 (5)	−0.0025 (5)	−0.0031 (5)

O2—C10	1.2334 (19)	C11—H11B	0.9600
N1—C10	1.3571 (19)	C11—H11C	0.9600
N1—C9	1.4687 (19)	C1—C2	1.389 (2)
N1—C12	1.470 (2)	C1—H1	0.9300
C12—C13	1.532 (2)	C16—C15	1.541 (2)
C12—C16	1.548 (2)	C16—H16A	0.9700
C12—H12	0.9800	C16—H16B	0.9700
C5—C6	1.386 (2)	C13—C14	1.523 (2)
C5—C4	1.391 (2)	C13—H13A	0.9700
C5—C9	1.520 (2)	C13—H13B	0.9700
C9—C8	1.551 (2)	C3—C2	1.394 (2)
C9—H9	0.9800	C3—H3	0.9300
C6—C1	1.391 (2)	C14—C15	1.539 (2)
C6—C7	1.476 (2)	C14—H14A	0.9700
C10—C11	1.511 (2)	C14—H14B	0.9700
C4—C3	1.390 (2)	C2—H2	0.9300
C4—H4	0.9300	C8—H8A	0.9700
C7—O1	1.2196 (19)	C8—H8B	0.9700
C7—C8	1.514 (2)	C15—H15A	0.9700
C11—H11A	0.9600	C15—H15B	0.9700
C10—N1—C9	118.39 (12)	C6—C1—H1	120.8
C10—N1—C12	124.30 (12)	C15—C16—C12	105.69 (12)
C9—N1—C12	117.30 (12)	C15—C16—H16A	110.6
N1—C12—C13	114.87 (12)	C12—C16—H16A	110.6
N1—C12—C16	114.41 (12)	C15—C16—H16B	110.6
C13—C12—C16	105.21 (12)	C12—C16—H16B	110.6
N1—C12—H12	107.3	H16A—C16—H16B	108.7
C13—C12—H12	107.3	C14—C13—C12	102.50 (12)
C16—C12—H12	107.3	C14—C13—H13A	111.3
C6—C5—C4	120.02 (14)	C12—C13—H13A	111.3
C6—C5—C9	111.41 (13)	C14—C13—H13B	111.3
C4—C5—C9	128.47 (14)	C12—C13—H13B	111.3
N1—C9—C5	115.14 (12)	H13A—C13—H13B	109.2
N1—C9—C8	115.99 (12)	C4—C3—C2	120.98 (15)
C5—C9—C8	103.95 (12)	C4—C3—H3	119.5
N1—C9—H9	107.1	C2—C3—H3	119.5
C5—C9—H9	107.1	C13—C14—C15	104.59 (12)
C8—C9—H9	107.1	C13—C14—H14A	110.8
C5—C6—C1	121.56 (14)	C15—C14—H14A	110.8
C5—C6—C7	110.07 (13)	C13—C14—H14B	110.8
C1—C6—C7	128.36 (14)	C15—C14—H14B	110.8
O2—C10—N1	120.77 (14)	H14A—C14—H14B	108.9
O2—C10—C11	120.75 (13)	C1—C2—C3	120.27 (15)
N1—C10—C11	118.48 (13)	C1—C2—H2	119.9
C3—C4—C5	118.77 (15)	C3—C2—H2	119.9
C3—C4—H4	120.6	C7—C8—C9	106.08 (12)
C5—C4—H4	120.6	C7—C8—H8A	110.5
O1—C7—C6	126.77 (15)	C9—C8—H8A	110.5
O1—C7—C8	125.44 (14)	C7—C8—H8B	110.5
C6—C7—C8	107.79 (13)	C9—C8—H8B	110.5
C10—C11—H11A	109.5	H8A—C8—H8B	108.7
C10—C11—H11B	109.5	C14—C15—C16	105.85 (12)
H11A—C11—H11B	109.5	C14—C15—H15A	110.6
C10—C11—H11C	109.5	C16—C15—H15A	110.6
H11A—C11—H11C	109.5	C14—C15—H15B	110.6
H11B—C11—H11C	109.5	C16—C15—H15B	110.6
C2—C1—C6	118.40 (15)	H15A—C15—H15B	108.7
C2—C1—H1	120.8
C10—N1—C12—C13	−118.48 (15)	C9—C5—C4—C3	176.96 (14)
C9—N1—C12—C13	62.40 (16)	C5—C6—C7—O1	−179.07 (14)
C10—N1—C12—C16	119.67 (15)	C1—C6—C7—O1	2.3 (2)
C9—N1—C12—C16	−59.45 (16)	C5—C6—C7—C8	1.59 (16)
C10—N1—C9—C5	60.63 (17)	C1—C6—C7—C8	−177.04 (14)
C12—N1—C9—C5	−120.20 (14)	C5—C6—C1—C2	−0.1 (2)
C10—N1—C9—C8	−61.05 (17)	C7—C6—C1—C2	178.36 (14)
C12—N1—C9—C8	118.12 (14)	N1—C12—C16—C15	147.25 (12)
C6—C5—C9—N1	−135.65 (13)	C13—C12—C16—C15	20.25 (16)
C4—C5—C9—N1	48.1 (2)	N1—C12—C13—C14	−163.79 (12)
C6—C5—C9—C8	−7.66 (16)	C16—C12—C13—C14	−37.07 (15)
C4—C5—C9—C8	176.08 (14)	C5—C4—C3—C2	−0.6 (2)
C4—C5—C6—C1	−0.7 (2)	C12—C13—C14—C15	39.78 (15)
C9—C5—C6—C1	−177.28 (13)	C6—C1—C2—C3	0.6 (2)
C4—C5—C6—C7	−179.41 (12)	C4—C3—C2—C1	−0.2 (2)
C9—C5—C6—C7	3.98 (16)	O1—C7—C8—C9	174.40 (14)
C9—N1—C10—O2	−0.8 (2)	C6—C7—C8—C9	−6.25 (16)
C12—N1—C10—O2	−179.91 (12)	N1—C9—C8—C7	135.64 (13)
C9—N1—C10—C11	178.57 (12)	C5—C9—C8—C7	8.18 (15)
C12—N1—C10—C11	−0.5 (2)	C13—C14—C15—C16	−27.47 (16)
C6—C5—C4—C3	1.0 (2)	C12—C16—C15—C14	4.32 (16)