4-{[(1S,2R)-2-Hy-droxy-indan-1-yl]amino}-pent-3-en-2-one.

In the mol-ecule of the title compound, C(14)H(17)NO(2), the dihedral angle formed by the mean planes through the indan ring system and the amino-pentenone fragment is 83.26 (13)°. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked into one-dimensional chains extending along the [010] direction via O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For metal complexes containing amino­indanol ligands, see: Lee et al. (2007 ▶); Flores-Lopes et al. (2000 ▶). For metal comlexes with acetyl­acetonate-type ligands, see: Patra et al. (2004 ▶); Jackson et al. (2006 ▶); Young et al. (2011 ▶).

Experimental

Crystal data

C14H17NO2

M = 231.29

Orthorhombic,

a = 8.3472 (5) Å

b = 11.2211 (7) Å

c = 13.4104 (9) Å

V = 1256.08 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.988, T max = 0.992

18304 measured reflections

1551 independent reflections

1198 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.095

S = 1.07

1551 reflections

164 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031169/rz2785sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812031169/rz2785Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031169/rz2785Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812031169/rz2785Isup4.cml

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

C14H17NO2	Z = 4
Mr = 231.29	F(000) = 496
Orthorhombic, P212121	Dx = 1.223 Mg m−3
Hall symbol: P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 8.3472 (5) Å	µ = 0.08 mm−1
b = 11.2211 (7) Å	T = 296 K
c = 13.4104 (9) Å	Block, white
V = 1256.08 (14) Å3	0.15 × 0.12 × 0.10 mm

Bruker APEXII CCD diffractometer	1551 independent reflections
Radiation source: fine-focus sealed tube	1198 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.988, Tmax = 0.992	k = −14→14
18304 measured reflections	l = −16→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.1264P] where P = (Fo2 + 2Fc2)/3
1551 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.12 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
N1	0.3729 (3)	0.46783 (17)	0.05082 (14)	0.0483 (5)
H201	0.397 (3)	0.429 (2)	0.1058 (17)	0.051 (7)*
O1	0.5423 (2)	0.58830 (16)	0.19665 (13)	0.0554 (5)
H101	0.564 (4)	0.634 (3)	0.240 (2)	0.073 (10)*
O2	0.3822 (2)	0.25196 (16)	0.14989 (12)	0.0616 (5)
C1	0.1505 (4)	0.8140 (3)	0.2132 (2)	0.0750 (9)
H1	0.1775	0.8852	0.2445	0.090*
C2	−0.0019 (5)	0.7674 (4)	0.2230 (2)	0.0906 (12)
H2	−0.0781	0.8080	0.2606	0.109*
C3	−0.0421 (4)	0.6613 (4)	0.1774 (2)	0.0845 (10)
H3	−0.1451	0.6311	0.1848	0.101*
C4	0.0692 (3)	0.5991 (3)	0.1208 (2)	0.0629 (7)
H4	0.0420	0.5274	0.0904	0.075*
C5	0.2214 (3)	0.6462 (2)	0.11056 (16)	0.0476 (6)
C6	0.2630 (3)	0.7535 (2)	0.15616 (16)	0.0510 (6)
C7	0.3656 (3)	0.5968 (2)	0.05584 (16)	0.0452 (5)
H7	0.3632	0.6275	−0.0126	0.054*
C8	0.5060 (3)	0.6566 (2)	0.11036 (17)	0.0505 (6)
H8	0.5997	0.6638	0.0667	0.061*
C9	0.4372 (3)	0.7797 (2)	0.13634 (19)	0.0582 (7)
H9A	0.4889	0.8127	0.1949	0.070*
H9B	0.4495	0.8348	0.0812	0.070*
C10	0.2653 (4)	0.4617 (2)	−0.11916 (16)	0.0625 (7)
H10A	0.1859	0.5216	−0.1060	0.094*
H10B	0.2224	0.4038	−0.1646	0.094*
H10C	0.3583	0.4982	−0.1481	0.094*
C11	0.3113 (3)	0.4010 (2)	−0.02268 (15)	0.0464 (6)
C12	0.2908 (3)	0.2795 (2)	−0.01416 (18)	0.0533 (6)
H12	0.2533	0.2394	−0.0702	0.064*
C13	0.3212 (3)	0.2108 (2)	0.07099 (19)	0.0508 (6)
C14	0.2757 (4)	0.0807 (2)	0.0684 (2)	0.0757 (9)
H14A	0.3551	0.0349	0.1033	0.113*
H14B	0.2697	0.0543	0.0005	0.113*
H14C	0.1735	0.0701	0.1000	0.113*

	U11	U22	U33	U12	U13	U23
N1	0.0661 (13)	0.0434 (11)	0.0353 (9)	−0.0011 (11)	−0.0078 (10)	0.0043 (9)
O1	0.0607 (11)	0.0556 (11)	0.0498 (10)	−0.0050 (9)	−0.0098 (9)	−0.0020 (9)
O2	0.0826 (12)	0.0542 (10)	0.0479 (9)	−0.0051 (10)	−0.0098 (10)	0.0080 (9)
C1	0.110 (3)	0.0578 (17)	0.0568 (16)	0.0261 (19)	0.0156 (18)	0.0162 (14)
C2	0.086 (3)	0.102 (3)	0.084 (2)	0.044 (2)	0.031 (2)	0.039 (2)
C3	0.0562 (18)	0.116 (3)	0.081 (2)	0.016 (2)	0.0068 (17)	0.041 (2)
C4	0.0527 (16)	0.0772 (18)	0.0587 (15)	0.0003 (15)	−0.0092 (13)	0.0167 (15)
C5	0.0506 (15)	0.0525 (14)	0.0398 (12)	0.0034 (12)	−0.0039 (11)	0.0123 (11)
C6	0.0691 (17)	0.0434 (13)	0.0406 (11)	0.0078 (13)	0.0052 (12)	0.0107 (11)
C7	0.0595 (14)	0.0417 (12)	0.0344 (10)	−0.0033 (12)	−0.0017 (11)	0.0053 (10)
C8	0.0526 (15)	0.0533 (14)	0.0455 (13)	−0.0084 (12)	0.0072 (11)	0.0022 (12)
C9	0.0829 (19)	0.0444 (14)	0.0473 (13)	−0.0088 (13)	−0.0013 (14)	0.0063 (11)
C10	0.086 (2)	0.0582 (15)	0.0431 (12)	0.0037 (16)	−0.0140 (14)	−0.0024 (12)
C11	0.0524 (14)	0.0533 (14)	0.0335 (11)	0.0031 (12)	−0.0023 (10)	−0.0016 (10)
C12	0.0666 (16)	0.0505 (15)	0.0428 (12)	−0.0006 (13)	−0.0089 (12)	−0.0066 (11)
C13	0.0530 (15)	0.0484 (14)	0.0510 (14)	0.0014 (12)	0.0005 (12)	−0.0005 (11)
C14	0.096 (2)	0.0504 (15)	0.0802 (19)	−0.0035 (16)	−0.0055 (18)	0.0013 (15)

N1—C11	1.341 (3)	C7—C8	1.536 (3)
N1—C7	1.450 (3)	C7—H7	0.9800
N1—H201	0.88 (2)	C8—C9	1.536 (3)
O1—C8	1.421 (3)	C8—H8	0.9800
O1—H101	0.79 (3)	C9—H9A	0.9700
O2—C13	1.262 (3)	C9—H9B	0.9700
C1—C2	1.382 (5)	C10—C11	1.512 (3)
C1—C6	1.389 (4)	C10—H10A	0.9600
C1—H1	0.9300	C10—H10B	0.9600
C2—C3	1.380 (5)	C10—H10C	0.9600
C2—H2	0.9300	C11—C12	1.379 (3)
C3—C4	1.388 (4)	C12—C13	1.401 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.383 (4)	C13—C14	1.509 (3)
C4—H4	0.9300	C14—H14A	0.9600
C5—C6	1.395 (4)	C14—H14B	0.9600
C5—C7	1.515 (3)	C14—H14C	0.9600
C6—C9	1.507 (4)
C11—N1—C7	125.2 (2)	O1—C8—H8	111.1
C11—N1—H201	115.0 (15)	C7—C8—H8	111.1
C7—N1—H201	118.0 (15)	C9—C8—H8	111.1
C8—O1—H101	107 (2)	C6—C9—C8	103.0 (2)
C2—C1—C6	119.3 (3)	C6—C9—H9A	111.2
C2—C1—H1	120.3	C8—C9—H9A	111.2
C6—C1—H1	120.3	C6—C9—H9B	111.2
C3—C2—C1	120.5 (3)	C8—C9—H9B	111.2
C3—C2—H2	119.7	H9A—C9—H9B	109.1
C1—C2—H2	119.7	C11—C10—H10A	109.5
C2—C3—C4	120.9 (3)	C11—C10—H10B	109.5
C2—C3—H3	119.5	H10A—C10—H10B	109.5
C4—C3—H3	119.5	C11—C10—H10C	109.5
C5—C4—C3	118.5 (3)	H10A—C10—H10C	109.5
C5—C4—H4	120.8	H10B—C10—H10C	109.5
C3—C4—H4	120.8	N1—C11—C12	122.7 (2)
C4—C5—C6	121.0 (2)	N1—C11—C10	118.3 (2)
C4—C5—C7	129.7 (2)	C12—C11—C10	119.0 (2)
C6—C5—C7	109.3 (2)	C11—C12—C13	126.1 (2)
C1—C6—C5	119.7 (3)	C11—C12—H12	117.0
C1—C6—C9	130.8 (3)	C13—C12—H12	117.0
C5—C6—C9	109.4 (2)	O2—C13—C12	123.7 (2)
N1—C7—C5	114.9 (2)	O2—C13—C14	118.3 (2)
N1—C7—C8	115.2 (2)	C12—C13—C14	117.9 (2)
C5—C7—C8	102.48 (17)	C13—C14—H14A	109.5
N1—C7—H7	107.9	C13—C14—H14B	109.5
C5—C7—H7	107.9	H14A—C14—H14B	109.5
C8—C7—H7	107.9	C13—C14—H14C	109.5
O1—C8—C7	108.34 (18)	H14A—C14—H14C	109.5
O1—C8—C9	112.34 (19)	H14B—C14—H14C	109.5
C7—C8—C9	102.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2i	0.80 (3)	2.03 (3)	2.829 (2)	179 (4)
N1—H201···O2	0.88 (2)	2.08 (2)	2.764 (3)	134 (2)
C9—H9A···O2i	0.97	2.44	3.254 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O2i	0.80 (3)	2.03 (3)	2.829 (2)	179 (4)
N1—H201⋯O2	0.88 (2)	2.08 (2)	2.764 (3)	134 (2)
C9—H9A⋯O2i	0.97	2.44	3.254 (3)	141

Symmetry code: (i) .