5-[(2-Hy-droxy-eth-yl)(meth-yl)amino]-thio-phene-2-carbaldehyde.

In the title compound, C8H11NO2S, the aldehyde group is approximately coplanar with the thio-phene ring [maximum deviation = 0.023 (2) Å]. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds into supra-molecular chains propagating along the a-axis direction.

Related literature

For potential applications of thio­phene derivatives, see: Encinas (2002 ▶). For a related thio­phene derivative, see: Perašínová et al. (2006 ▶).

Experimental

Crystal data

C8H11NO2S

M = 185.24

Orthorhombic,

a = 15.764 (5) Å

b = 5.136 (5) Å

c = 11.028 (5) Å

V = 892.9 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

5828 measured reflections

1564 independent reflections

1514 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.067

S = 1.08

1564 reflections

111 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Absolute structure: Flack (1983 ▶), 756 Friedel pairs

Absolute structure parameter: −0.03 (7)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S1600536814012021/xu5786sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012021/xu5786Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012021/xu5786Isup3.cml

CCDC reference: 996513

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H11NO2S	F(000) = 392
Mr = 185.24	Dx = 1.378 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2ac	Cell parameters from 3223 reflections
a = 15.764 (5) Å	θ = 2.6–26.8°
b = 5.136 (5) Å	µ = 0.32 mm−1
c = 11.028 (5) Å	T = 293 K
V = 892.9 (10) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker SMART 1000 CCD area-detector diffractometer	1514 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
phi and ω scans	h = −17→18
5828 measured reflections	k = −5→6
1564 independent reflections	l = −13→13

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)] = 0.024	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.0567P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1564 reflections	Δρmax = 0.14 e Å−3
111 parameters	Δρmin = −0.13 e Å−3
1 restraint	Absolute structure: Flack (1983), 756 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (7)

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	0.53676 (3)	0.28672 (8)	0.22080 (5)	0.04276 (14)
O1	0.32880 (9)	0.3310 (3)	0.35492 (15)	0.0575 (4)
H1	0.2888	0.2479	0.3274	0.086*
N1	0.40014 (10)	0.5376 (3)	0.13076 (14)	0.0446 (4)
C4	0.45817 (10)	0.3498 (4)	0.11400 (16)	0.0385 (4)
C5	0.46620 (12)	0.1849 (4)	0.01313 (18)	0.0459 (5)
H5	0.4301	0.1889	−0.0535	0.055*
C6	0.53411 (13)	0.0157 (4)	0.02439 (17)	0.0501 (5)
H6	0.5479	−0.1056	−0.0351	0.060*
C7	0.57958 (11)	0.0402 (4)	0.12977 (19)	0.0457 (4)
O2	0.68678 (9)	−0.0828 (4)	0.26743 (18)	0.0723 (5)
C2	0.39359 (13)	0.6822 (3)	0.24362 (18)	0.0460 (5)
H2A	0.3870	0.8658	0.2251	0.055*
H2B	0.4459	0.6617	0.2888	0.055*
C1	0.33673 (14)	0.5845 (5)	0.0376 (2)	0.0583 (6)
H1A	0.3644	0.6127	−0.0389	0.087*
H1B	0.3040	0.7356	0.0585	0.087*
H1C	0.2999	0.4362	0.0315	0.087*
C8	0.64980 (13)	−0.1077 (4)	0.1692 (2)	0.0553 (5)
H8	0.6700	−0.2351	0.1167	0.066*
C3	0.32038 (12)	0.5959 (4)	0.32204 (19)	0.0490 (5)
H3A	0.3184	0.7022	0.3947	0.059*
H3B	0.2676	0.6204	0.2783	0.059*

	U11	U22	U33	U12	U13	U23
S1	0.0454 (2)	0.0426 (2)	0.0403 (2)	0.00002 (17)	−0.0065 (2)	−0.0035 (3)
O1	0.0509 (8)	0.0526 (8)	0.0689 (10)	−0.0042 (7)	−0.0065 (8)	0.0180 (7)
N1	0.0451 (8)	0.0484 (9)	0.0403 (7)	0.0028 (7)	−0.0043 (7)	0.0008 (7)
C4	0.0413 (10)	0.0403 (9)	0.0338 (9)	−0.0082 (7)	0.0010 (7)	0.0035 (8)
C5	0.0524 (12)	0.0537 (12)	0.0317 (9)	−0.0072 (9)	0.0002 (8)	−0.0023 (8)
C6	0.0592 (13)	0.0510 (12)	0.0400 (10)	−0.0036 (9)	0.0120 (9)	−0.0060 (9)
C7	0.0433 (10)	0.0437 (10)	0.0500 (9)	−0.0024 (8)	0.0106 (8)	0.0003 (8)
O2	0.0587 (9)	0.0613 (10)	0.0969 (13)	0.0069 (8)	−0.0212 (9)	0.0000 (9)
C2	0.0446 (9)	0.0380 (9)	0.0555 (14)	−0.0031 (7)	0.0037 (8)	−0.0050 (8)
C1	0.0518 (12)	0.0673 (15)	0.0558 (12)	0.0036 (11)	−0.0106 (9)	0.0090 (10)
C8	0.0484 (11)	0.0469 (12)	0.0705 (13)	0.0010 (10)	0.0064 (12)	0.0012 (10)
C3	0.0494 (11)	0.0427 (10)	0.0550 (12)	0.0026 (9)	0.0057 (9)	−0.0005 (9)

S1—C4	1.7398 (18)	C7—C8	1.411 (3)
S1—C7	1.751 (2)	O2—C8	1.237 (3)
O1—C3	1.414 (3)	C2—C3	1.509 (3)
O1—H1	0.8200	C2—H2A	0.9700
N1—C4	1.342 (3)	C2—H2B	0.9700
N1—C2	1.453 (2)	C1—H1A	0.9600
N1—C1	1.454 (3)	C1—H1B	0.9600
C4—C5	1.404 (3)	C1—H1C	0.9600
C5—C6	1.384 (3)	C8—H8	0.9300
C5—H5	0.9300	C3—H3A	0.9700
C6—C7	1.371 (3)	C3—H3B	0.9700
C6—H6	0.9300
C4—S1—C7	91.21 (10)	C3—C2—H2A	108.9
C3—O1—H1	109.5	N1—C2—H2B	108.9
C4—N1—C2	122.26 (16)	C3—C2—H2B	108.9
C4—N1—C1	119.38 (17)	H2A—C2—H2B	107.7
C2—N1—C1	118.15 (17)	N1—C1—H1A	109.5
N1—C4—C5	127.17 (17)	N1—C1—H1B	109.5
N1—C4—S1	121.74 (14)	H1A—C1—H1B	109.5
C5—C4—S1	111.08 (15)	N1—C1—H1C	109.5
C6—C5—C4	112.17 (18)	H1A—C1—H1C	109.5
C6—C5—H5	123.9	H1B—C1—H1C	109.5
C4—C5—H5	123.9	O2—C8—C7	125.7 (2)
C7—C6—C5	114.99 (18)	O2—C8—H8	117.1
C7—C6—H6	122.5	C7—C8—H8	117.1
C5—C6—H6	122.5	O1—C3—C2	110.98 (15)
C6—C7—C8	128.45 (19)	O1—C3—H3A	109.4
C6—C7—S1	110.53 (15)	C2—C3—H3A	109.4
C8—C7—S1	120.99 (17)	O1—C3—H3B	109.4
N1—C2—C3	113.27 (16)	C2—C3—H3B	109.4
N1—C2—H2A	108.9	H3A—C3—H3B	108.0
C2—N1—C4—C5	174.75 (18)	C5—C6—C7—C8	177.8 (2)
C1—N1—C4—C5	0.2 (3)	C5—C6—C7—S1	−0.2 (2)
C2—N1—C4—S1	−6.4 (2)	C4—S1—C7—C6	0.14 (15)
C1—N1—C4—S1	179.03 (15)	C4—S1—C7—C8	−178.05 (16)
C7—S1—C4—N1	−179.10 (15)	C4—N1—C2—C3	−103.3 (2)
C7—S1—C4—C5	−0.06 (15)	C1—N1—C2—C3	71.4 (2)
N1—C4—C5—C6	178.94 (18)	C6—C7—C8—O2	−177.4 (2)
S1—C4—C5—C6	0.0 (2)	S1—C7—C8—O2	0.5 (3)
C4—C5—C6—C7	0.1 (2)	N1—C2—C3—O1	60.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.93	2.751 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.93	2.751 (2)	174

Symmetry code: (i) .