5-tert-Butyl-2-hy-droxy-3-(2-thien-yl)benzaldehyde.

In the crystal structure of the title compound, C(15)H(16)O(2)S, the thio-phene ring is essentially planar (r.m.s. deviation = 0.006 Å for all non-H atoms) and roughly coplanar with the benzene ring, the dihedral angle between the mean planes of the rings being 4.35 (8)°. An intra-molecular O-H⋯O hydrogen bond is observed between the OH group and the aldehyde O atom.

Related literature

For related salicyl­aldehyde derivative compounds, see: Qiu et al. (2009 ▶); Yu et al. (2007 ▶); Wang et al. (2009 ▶); Wong et al. (2004 ▶).

Experimental

Crystal data

C15H16O2S

M = 260.34

Triclinic,

a = 7.2016 (14) Å

b = 8.9375 (18) Å

c = 10.922 (2) Å

α = 91.50 (3)°

β = 107.69 (3)°

γ = 93.25 (3)°

V = 668.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 173 K

0.10 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.977, T max = 0.977

5891 measured reflections

2705 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.208

S = 1.15

2705 reflections

179 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.45 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030382/zq2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030382/zq2050Isup2.hkl

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

C15H16O2S	Z = 2
Mr = 260.34	F(000) = 276
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2016 (14) Å	Cell parameters from 5891 reflections
b = 8.9375 (18) Å	θ = 3.0–26.4°
c = 10.922 (2) Å	µ = 0.23 mm−1
α = 91.50 (3)°	T = 173 K
β = 107.69 (3)°	Block, yellow
γ = 93.25 (3)°	0.10 × 0.10 × 0.10 mm
V = 668.0 (2) Å3

Rigaku R-AXIS RAPID diffractometer	2705 independent reflections
Radiation source: fine-focus sealed tube	1958 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 0 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.977, Tmax = 0.977	l = −13→13
5891 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.1265P)2 + 0.0566P] where P = (Fo2 + 2Fc2)/3
2705 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.41 e Å−3
9 restraints	Δρmin = −0.45 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
S1	0.39900 (12)	0.44272 (9)	0.30990 (6)	0.0798 (4)
O2	0.3088 (3)	0.6482 (2)	0.12395 (19)	0.0677 (5)
C15	0.2702 (3)	0.3967 (2)	0.0406 (2)	0.0482 (5)
C14	0.2152 (3)	0.3004 (2)	−0.0692 (2)	0.0496 (5)
H14A	0.2226	0.1957	−0.0574	0.060*
C13	0.1403 (3)	0.4992 (3)	−0.2105 (2)	0.0544 (6)
H13A	0.0979	0.5352	−0.2949	0.065*
C12	0.3408 (3)	0.3350 (3)	0.1694 (2)	0.0508 (5)
C11	0.1504 (3)	0.3476 (2)	−0.1946 (2)	0.0497 (5)
C10	0.2573 (3)	0.5507 (3)	0.0206 (2)	0.0507 (5)
C9	0.1912 (3)	0.6013 (3)	−0.1048 (2)	0.0556 (6)
C8	0.0927 (4)	0.2304 (3)	−0.3084 (2)	0.0564 (6)
C7	0.3726 (4)	0.1835 (3)	0.1953 (2)	0.0636 (6)
O1	0.2186 (4)	0.8609 (2)	−0.0407 (2)	0.0947 (7)
C6	0.1769 (5)	0.7611 (3)	−0.1262 (3)	0.0748 (8)
C5	0.4400 (4)	0.1649 (3)	0.3312 (3)	0.0721 (7)
H5A	0.4688	0.0706	0.3682	0.087*
C4	0.2655 (4)	0.1362 (3)	−0.3025 (2)	0.0716 (7)
H4A	0.3763	0.2017	−0.3080	0.107*
H4B	0.2283	0.0616	−0.3746	0.107*
H4C	0.3026	0.0851	−0.2212	0.107*
C3	0.0331 (5)	0.3042 (3)	−0.4383 (2)	0.0759 (8)
H3A	0.1425	0.3700	−0.4456	0.114*
H3B	−0.0795	0.3635	−0.4446	0.114*
H3C	−0.0017	0.2265	−0.5079	0.114*
C2	−0.0816 (4)	0.1276 (3)	−0.2998 (3)	0.0757 (8)
H2A	−0.1191	0.0532	−0.3721	0.114*
H2B	−0.1922	0.1881	−0.3032	0.114*
H2C	−0.0443	0.0761	−0.2187	0.114*
C1	0.4584 (4)	0.2933 (4)	0.4010 (3)	0.0765 (8)
H7	0.354 (6)	0.109 (3)	0.140 (3)	0.127 (14)*
H2	0.504 (4)	0.303 (4)	0.4875 (10)	0.082 (9)*
H6A	0.135 (6)	0.804 (5)	−0.213 (4)	0.127 (14)*
H2D	0.292 (4)	0.726 (4)	0.093 (3)	0.068 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.1003 (6)	0.0763 (6)	0.0558 (5)	0.0081 (4)	0.0148 (4)	−0.0179 (3)
O2	0.0845 (13)	0.0497 (11)	0.0657 (11)	−0.0018 (9)	0.0210 (10)	−0.0186 (9)
C15	0.0443 (11)	0.0505 (12)	0.0496 (11)	−0.0004 (9)	0.0157 (9)	−0.0095 (9)
C14	0.0550 (12)	0.0418 (11)	0.0503 (12)	0.0017 (9)	0.0146 (10)	−0.0067 (9)
C13	0.0561 (13)	0.0525 (13)	0.0551 (12)	0.0022 (10)	0.0183 (10)	−0.0028 (10)
C12	0.0469 (11)	0.0555 (13)	0.0485 (11)	−0.0001 (9)	0.0142 (9)	−0.0107 (9)
C11	0.0525 (12)	0.0471 (12)	0.0487 (11)	0.0010 (9)	0.0155 (9)	−0.0064 (9)
C10	0.0485 (11)	0.0472 (12)	0.0572 (12)	−0.0019 (9)	0.0197 (10)	−0.0134 (9)
C9	0.0594 (13)	0.0449 (12)	0.0653 (14)	−0.0011 (10)	0.0245 (11)	−0.0063 (10)
C8	0.0670 (14)	0.0505 (13)	0.0484 (12)	0.0005 (10)	0.0144 (10)	−0.0097 (9)
C7	0.0820 (15)	0.0581 (13)	0.0452 (11)	0.0039 (11)	0.0118 (10)	0.0004 (9)
O1	0.141 (2)	0.0451 (11)	0.0976 (15)	−0.0011 (11)	0.0388 (14)	−0.0120 (10)
C6	0.098 (2)	0.0475 (14)	0.0825 (19)	0.0032 (13)	0.0332 (17)	−0.0002 (13)
C5	0.0849 (15)	0.0702 (14)	0.0555 (11)	0.0096 (12)	0.0121 (11)	0.0049 (10)
C4	0.0867 (19)	0.0661 (16)	0.0595 (14)	0.0129 (13)	0.0186 (13)	−0.0165 (12)
C3	0.100 (2)	0.0675 (17)	0.0505 (13)	0.0057 (15)	0.0103 (13)	−0.0100 (12)
C2	0.0847 (19)	0.0693 (17)	0.0667 (16)	−0.0170 (14)	0.0193 (14)	−0.0210 (13)
C1	0.0772 (18)	0.097 (2)	0.0504 (14)	0.0074 (15)	0.0124 (13)	−0.0067 (14)

S1—C1	1.683 (3)	C8—C2	1.541 (4)
S1—C12	1.716 (2)	C7—C5	1.432 (3)
O2—C10	1.352 (3)	C7—H7	0.867 (10)
O2—H2D	0.78 (3)	O1—C6	1.230 (3)
C15—C14	1.399 (3)	C6—H6A	0.99 (4)
C15—C10	1.402 (3)	C5—C1	1.339 (4)
C15—C12	1.476 (3)	C5—H5A	0.9500
C14—C11	1.391 (3)	C4—H4A	0.9800
C14—H14A	0.9500	C4—H4B	0.9800
C13—C11	1.374 (3)	C4—H4C	0.9800
C13—C9	1.396 (3)	C3—H3A	0.9800
C13—H13A	0.9500	C3—H3B	0.9800
C12—C7	1.408 (3)	C3—H3C	0.9800
C11—C8	1.544 (3)	C2—H2A	0.9800
C10—C9	1.403 (3)	C2—H2B	0.9800
C9—C6	1.457 (4)	C2—H2C	0.9800
C8—C4	1.527 (4)	C1—H2	0.902 (10)
C8—C3	1.530 (4)
C1—S1—C12	92.60 (13)	C12—C7—H7	127 (3)
C10—O2—H2D	103 (2)	C5—C7—H7	122 (3)
C14—C15—C10	116.7 (2)	O1—C6—C9	125.0 (3)
C14—C15—C12	120.00 (19)	O1—C6—H6A	111 (2)
C10—C15—C12	123.30 (19)	C9—C6—H6A	124 (3)
C11—C14—C15	124.4 (2)	C1—C5—C7	113.4 (3)
C11—C14—H14A	117.8	C1—C5—H5A	123.3
C15—C14—H14A	117.8	C7—C5—H5A	123.3
C11—C13—C9	121.2 (2)	C8—C4—H4A	109.5
C11—C13—H13A	119.4	C8—C4—H4B	109.5
C9—C13—H13A	119.4	H4A—C4—H4B	109.5
C7—C12—C15	125.95 (19)	C8—C4—H4C	109.5
C7—C12—S1	110.58 (17)	H4A—C4—H4C	109.5
C15—C12—S1	123.46 (17)	H4B—C4—H4C	109.5
C13—C11—C14	117.3 (2)	C8—C3—H3A	109.5
C13—C11—C8	123.0 (2)	C8—C3—H3B	109.5
C14—C11—C8	119.69 (19)	H3A—C3—H3B	109.5
O2—C10—C15	118.8 (2)	C8—C3—H3C	109.5
O2—C10—C9	121.1 (2)	H3A—C3—H3C	109.5
C15—C10—C9	120.13 (19)	H3B—C3—H3C	109.5
C13—C9—C10	120.3 (2)	C8—C2—H2A	109.5
C13—C9—C6	119.3 (2)	C8—C2—H2B	109.5
C10—C9—C6	120.3 (2)	H2A—C2—H2B	109.5
C4—C8—C3	108.3 (2)	C8—C2—H2C	109.5
C4—C8—C2	109.5 (2)	H2A—C2—H2C	109.5
C3—C8—C2	108.3 (2)	H2B—C2—H2C	109.5
C4—C8—C11	109.58 (19)	C5—C1—S1	112.9 (2)
C3—C8—C11	111.9 (2)	C5—C1—H2	125 (2)
C2—C8—C11	109.16 (19)	S1—C1—H2	122 (2)
C12—C7—C5	110.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···O1	0.78 (3)	1.89 (3)	2.623 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2D⋯O1	0.78 (3)	1.89 (3)	2.623 (3)	157 (3)