(1S,2R)-1-[(E)-(Thio-phen-2-yl-methyl-idene)amino]-indan-2-ol.

In the title compound, C(14)H(13)NOS, the dihedral angle formed by the mean planes through the indane ring system and the thio-phene ring is 85.04 (11)°. The imine bond is located in the thio-phene plane [the S-C-C-N torsion angle is 0.00 (3)°] and an intra-molecular O-H⋯N hydrogen bond is observed.

Related literature

For metal complexes containing amino­indanol ligands, see: Lee et al. (2007 ▶); Flores-Lopes et al. (2000 ▶). For metal comlexes with thio­phene-type ligands, see: Jeong et al. (2011 ▶); Dong et al. (2006 ▶); Lee et al. (1999 ▶).

Experimental

Crystal data

C14H13NOS

M = 243.31

Monoclinic,

a = 5.8640 (2) Å

b = 13.4454 (5) Å

c = 8.0118 (3) Å

β = 92.258 (2)°

V = 631.19 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.943, T max = 0.965

7148 measured reflections

3182 independent reflections

2848 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 1.03

3182 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1201 Friedel pairs

Flack parameter: 0.06 (8)

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/S1600536812032783/ff2077sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032783/ff2077Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032783/ff2077Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812032783/ff2077Isup4.cml

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

C14H13NOS	F(000) = 256
Mr = 243.31	Dx = 1.280 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5424 reflections
a = 5.8640 (2) Å	θ = 2.5–30.4°
b = 13.4454 (5) Å	µ = 0.24 mm−1
c = 8.0118 (3) Å	T = 296 K
β = 92.258 (2)°	Block, white
V = 631.19 (4) Å3	0.25 × 0.20 × 0.15 mm
Z = 2

Bruker APEXII CCD diffractometer	3182 independent reflections
Radiation source: fine-focus sealed tube	2848 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→7
Tmin = 0.943, Tmax = 0.965	k = −15→18
7148 measured reflections	l = −11→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.131	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3182 reflections	Δρmax = 0.25 e Å−3
155 parameters	Δρmin = −0.27 e Å−3
1 restraint	Absolute structure: Flack (1983), 1201 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (8)

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
O	0.3762 (3)	0.41344 (15)	0.6763 (2)	0.0694 (4)
H1	0.3962	0.4736	0.6845	0.104*
S	0.84192 (7)	0.69970 (5)	0.55448 (6)	0.05798 (16)
C9	0.3596 (3)	0.40337 (14)	1.0537 (2)	0.0437 (4)
C14	0.5379 (3)	0.46986 (12)	1.0333 (2)	0.0431 (3)
C4	1.0148 (3)	0.64078 (15)	0.7010 (2)	0.0473 (4)
C13	0.5668 (4)	0.55083 (16)	1.1369 (3)	0.0602 (5)
H13	0.6866	0.5950	1.1232	0.072*
C3	1.2263 (3)	0.68631 (19)	0.7167 (3)	0.0552 (5)
H3	1.3433	0.6657	0.7904	0.066*
C1	1.0474 (3)	0.78383 (18)	0.5133 (3)	0.0567 (5)
H1A	1.0286	0.8349	0.4356	0.068*
C5	0.9397 (3)	0.55622 (17)	0.7985 (3)	0.0524 (4)
H5	1.0416	0.5274	0.8761	0.063*
C6	0.6804 (3)	0.43819 (15)	0.8891 (3)	0.0508 (4)
H6	0.8190	0.4043	0.9312	0.061*
C2	1.2422 (3)	0.76835 (17)	0.6062 (3)	0.0573 (5)
H2	1.3724	0.8073	0.5985	0.069*
C8	0.3710 (4)	0.32062 (16)	0.9292 (3)	0.0570 (5)
H8A	0.2204	0.3041	0.8830	0.068*
H8B	0.4395	0.2616	0.9794	0.068*
C7	0.5206 (4)	0.36346 (16)	0.7957 (3)	0.0574 (5)
H7	0.6085	0.3110	0.7428	0.069*
C12	0.4134 (6)	0.5654 (2)	1.2626 (3)	0.0789 (8)
H12	0.4314	0.6194	1.3345	0.095*
C10	0.2064 (4)	0.4177 (2)	1.1781 (3)	0.0594 (5)
H10	0.0874	0.3732	1.1925	0.071*
C11	0.2347 (5)	0.5002 (3)	1.2812 (3)	0.0742 (7)
H11	0.1313	0.5117	1.3641	0.089*
N	0.7401 (3)	0.52068 (15)	0.7810 (2)	0.0549 (4)

	U11	U22	U33	U12	U13	U23
O	0.0800 (10)	0.0776 (11)	0.0494 (8)	−0.0161 (9)	−0.0110 (7)	0.0048 (8)
S	0.0389 (2)	0.0805 (3)	0.0542 (3)	0.0031 (2)	−0.00272 (16)	0.0050 (3)
C9	0.0500 (8)	0.0434 (8)	0.0370 (8)	0.0001 (6)	−0.0051 (6)	0.0072 (6)
C14	0.0453 (8)	0.0416 (8)	0.0418 (8)	0.0025 (6)	−0.0075 (6)	0.0049 (7)
C4	0.0335 (7)	0.0623 (10)	0.0462 (9)	0.0047 (6)	0.0029 (6)	0.0021 (8)
C13	0.0775 (14)	0.0474 (10)	0.0549 (12)	−0.0071 (9)	−0.0102 (10)	0.0007 (9)
C3	0.0331 (6)	0.0706 (13)	0.0619 (11)	0.0030 (8)	0.0003 (6)	0.0081 (10)
C1	0.0487 (9)	0.0717 (12)	0.0505 (11)	0.0071 (9)	0.0133 (8)	0.0074 (9)
C5	0.0376 (7)	0.0647 (12)	0.0548 (10)	0.0089 (7)	0.0015 (7)	0.0091 (9)
C6	0.0395 (8)	0.0552 (10)	0.0576 (11)	0.0098 (7)	0.0010 (7)	0.0069 (8)
C2	0.0385 (8)	0.0706 (13)	0.0634 (12)	−0.0013 (8)	0.0105 (8)	0.0034 (10)
C8	0.0693 (12)	0.0416 (9)	0.0596 (13)	−0.0063 (8)	−0.0029 (9)	0.0023 (8)
C7	0.0661 (12)	0.0512 (10)	0.0552 (11)	0.0080 (8)	0.0043 (9)	−0.0086 (9)
C12	0.125 (2)	0.0626 (15)	0.0490 (13)	0.0113 (14)	−0.0034 (13)	−0.0128 (11)
C10	0.0629 (12)	0.0736 (14)	0.0417 (10)	−0.0035 (9)	0.0018 (8)	0.0130 (9)
C11	0.0851 (17)	0.0953 (19)	0.0427 (11)	0.0132 (14)	0.0091 (10)	0.0013 (12)
N	0.0383 (7)	0.0697 (11)	0.0569 (10)	0.0033 (7)	0.0031 (6)	0.0104 (8)

O—C7	1.421 (3)	C1—H1A	0.9300
O—H1	0.8200	C5—N	1.267 (3)
S—C1	1.695 (2)	C5—H5	0.9300
S—C4	1.7143 (19)	C6—N	1.458 (3)
C9—C10	1.381 (3)	C6—C7	1.546 (3)
C9—C14	1.390 (2)	C6—H6	0.9800
C9—C8	1.498 (3)	C2—H2	0.9300
C14—C13	1.376 (3)	C8—C7	1.523 (3)
C14—C6	1.513 (3)	C8—H8A	0.9700
C4—C3	1.384 (3)	C8—H8B	0.9700
C4—C5	1.457 (3)	C7—H7	0.9800
C13—C12	1.390 (4)	C12—C11	1.379 (5)
C13—H13	0.9300	C12—H12	0.9300
C3—C2	1.420 (3)	C10—C11	1.390 (4)
C3—H3	0.9300	C10—H10	0.9300
C1—C2	1.355 (3)	C11—H11	0.9300
C7—O—H1	109.5	C14—C6—H6	110.1
C1—S—C4	92.06 (10)	C7—C6—H6	110.1
C10—C9—C14	120.60 (19)	C1—C2—C3	112.79 (18)
C10—C9—C8	129.15 (19)	C1—C2—H2	123.6
C14—C9—C8	110.23 (16)	C3—C2—H2	123.6
C13—C14—C9	120.86 (19)	C9—C8—C7	103.23 (16)
C13—C14—C6	128.70 (18)	C9—C8—H8A	111.1
C9—C14—C6	110.44 (16)	C7—C8—H8A	111.1
C3—C4—C5	125.80 (18)	C9—C8—H8B	111.1
C3—C4—S	111.18 (15)	C7—C8—H8B	111.1
C5—C4—S	122.99 (14)	H8A—C8—H8B	109.1
C14—C13—C12	118.8 (2)	O—C7—C8	107.87 (19)
C14—C13—H13	120.6	O—C7—C6	110.60 (17)
C12—C13—H13	120.6	C8—C7—C6	105.13 (18)
C4—C3—C2	111.57 (17)	O—C7—H7	111.0
C4—C3—H3	124.2	C8—C7—H7	111.0
C2—C3—H3	124.2	C6—C7—H7	111.0
C2—C1—S	112.40 (17)	C11—C12—C13	120.3 (2)
C2—C1—H1A	123.8	C11—C12—H12	119.8
S—C1—H1A	123.8	C13—C12—H12	119.8
N—C5—C4	122.17 (19)	C9—C10—C11	118.3 (2)
N—C5—H5	118.9	C9—C10—H10	120.9
C4—C5—H5	118.9	C11—C10—H10	120.9
N—C6—C14	113.08 (16)	C12—C11—C10	121.1 (2)
N—C6—C7	111.23 (18)	C12—C11—H11	119.4
C14—C6—C7	102.12 (15)	C10—C11—H11	119.4
N—C6—H6	110.1	C5—N—C6	117.62 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O—H1···N	0.82	2.22	2.682 (3)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H1⋯N	0.82	2.22	2.682 (3)	116