4-(2-Thienylmethyl-eneamino)benzoic acid.

In the title mol-ecule, C(12)H(9)NO(2)S, the dihedral angle between benzene and thio-phene rings is 41.91 (8)°. The crystal packing exhibits short inter-molecular O-H⋯O and C-H⋯O hydrogen-bonding contacts.

Related literature

For the synthesis of substituted thio­phenes, see: Koike et al. (1999 ▶). For the anti­cancer activity of Schiff bases, see: Chakraborty & Patel (1996 ▶). For a related structure, see: Hu et al. (2008 ▶).

Experimental

Crystal data

C12H9NO2S

M = 231.26

Monoclinic,

a = 3.8801 (3) Å

b = 10.0849 (11) Å

c = 27.380 (3) Å

β = 93.185 (1)°

V = 1069.74 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.43 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.888, T max = 0.967

5213 measured reflections

1887 independent reflections

1496 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.140

S = 1.09

1887 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809039208/bq2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039208/bq2161Isup2.hkl

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

C12H9NO2S	F(000) = 480
Mr = 231.26	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1697 reflections
a = 3.8801 (3) Å	θ = 3.0–24.6°
b = 10.0849 (11) Å	µ = 0.28 mm−1
c = 27.380 (3) Å	T = 298 K
β = 93.185 (1)°	Block, red
V = 1069.74 (18) Å3	0.43 × 0.20 × 0.12 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1887 independent reflections
Radiation source: fine-focus sealed tube	1496 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.888, Tmax = 0.967	k = −12→9
5213 measured reflections	l = −29→32

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.4613P] where P = (Fo2 + 2Fc2)/3
1887 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.22 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	0.4137 (7)	0.4083 (2)	0.34590 (9)	0.0410 (6)
O1	0.9679 (7)	0.8245 (2)	0.50746 (8)	0.0580 (7)
H1	1.0383	0.8943	0.5197	0.087*
O2	0.7517 (7)	0.9632 (2)	0.45013 (7)	0.0543 (6)
S1	0.3211 (2)	0.18720 (8)	0.26947 (3)	0.0476 (3)
C1	0.2843 (8)	0.3008 (3)	0.36133 (11)	0.0438 (8)
H1A	0.2297	0.2954	0.3939	0.053*
C2	0.2192 (8)	0.1869 (3)	0.32997 (10)	0.0389 (7)
C3	0.0828 (9)	0.0673 (3)	0.34261 (11)	0.0472 (8)
H3	0.0114	0.0483	0.3737	0.057*
C4	0.0618 (9)	−0.0239 (3)	0.30361 (12)	0.0506 (9)
H4	−0.0252	−0.1094	0.3061	0.061*
C5	0.1821 (9)	0.0267 (3)	0.26221 (12)	0.0515 (9)
H5	0.1888	−0.0202	0.2330	0.062*
C6	0.8065 (8)	0.8483 (3)	0.46603 (10)	0.0397 (7)
C7	0.6845 (7)	0.7322 (3)	0.43688 (9)	0.0354 (7)
C8	0.7347 (8)	0.6033 (3)	0.45455 (10)	0.0403 (7)
H8	0.8320	0.5902	0.4860	0.048*
C9	0.6413 (8)	0.4952 (3)	0.42586 (10)	0.0419 (8)
H9	0.6774	0.4098	0.4379	0.050*
C10	0.4922 (7)	0.5141 (3)	0.37856 (10)	0.0358 (7)
C11	0.4398 (8)	0.6428 (3)	0.36128 (10)	0.0407 (7)
H11	0.3413	0.6561	0.3299	0.049*
C12	0.5320 (8)	0.7508 (3)	0.39001 (10)	0.0395 (7)
H12	0.4924	0.8362	0.3781	0.047*

	U11	U22	U33	U12	U13	U23
N1	0.0479 (16)	0.0341 (14)	0.0407 (14)	−0.0028 (12)	−0.0002 (11)	−0.0039 (11)
O1	0.0861 (18)	0.0389 (13)	0.0463 (13)	−0.0045 (12)	−0.0194 (12)	−0.0047 (10)
O2	0.0839 (18)	0.0321 (12)	0.0455 (12)	−0.0027 (12)	−0.0094 (11)	−0.0006 (10)
S1	0.0579 (6)	0.0426 (5)	0.0424 (5)	−0.0005 (4)	0.0042 (4)	−0.0011 (3)
C1	0.0488 (19)	0.0427 (18)	0.0404 (16)	0.0005 (15)	0.0060 (14)	−0.0051 (14)
C2	0.0392 (17)	0.0358 (16)	0.0414 (16)	0.0019 (14)	−0.0008 (13)	−0.0027 (13)
C3	0.055 (2)	0.0433 (19)	0.0432 (17)	−0.0036 (16)	0.0038 (15)	0.0041 (14)
C4	0.055 (2)	0.0341 (17)	0.062 (2)	−0.0043 (15)	−0.0028 (17)	−0.0020 (15)
C5	0.057 (2)	0.0443 (19)	0.052 (2)	0.0033 (17)	−0.0097 (16)	−0.0126 (16)
C6	0.0469 (19)	0.0373 (17)	0.0349 (15)	0.0007 (14)	0.0025 (13)	−0.0004 (13)
C7	0.0389 (17)	0.0316 (15)	0.0356 (15)	−0.0002 (13)	0.0011 (12)	−0.0021 (12)
C8	0.0497 (19)	0.0375 (16)	0.0327 (15)	0.0014 (14)	−0.0056 (13)	0.0000 (13)
C9	0.052 (2)	0.0308 (16)	0.0426 (17)	0.0016 (14)	−0.0003 (14)	0.0016 (13)
C10	0.0376 (17)	0.0364 (16)	0.0335 (15)	−0.0015 (13)	0.0025 (12)	−0.0049 (12)
C11	0.0470 (19)	0.0400 (17)	0.0341 (15)	−0.0011 (15)	−0.0058 (13)	0.0013 (13)
C12	0.0477 (18)	0.0302 (15)	0.0403 (16)	0.0011 (14)	−0.0005 (13)	0.0020 (13)

N1—C1	1.277 (4)	C4—H4	0.9300
N1—C10	1.414 (3)	C5—H5	0.9300
O1—C6	1.287 (3)	C6—C7	1.480 (4)
O1—H1	0.8200	C7—C12	1.396 (4)
O2—C6	1.252 (3)	C7—C8	1.397 (4)
S1—C5	1.714 (3)	C8—C9	1.380 (4)
S1—C2	1.724 (3)	C8—H8	0.9300
C1—C2	1.448 (4)	C9—C10	1.402 (4)
C1—H1A	0.9300	C9—H9	0.9300
C2—C3	1.369 (4)	C10—C11	1.392 (4)
C3—C4	1.408 (4)	C11—C12	1.379 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.350 (4)	C12—H12	0.9300
C1—N1—C10	120.4 (3)	O1—C6—C7	116.9 (3)
C6—O1—H1	109.5	C12—C7—C8	119.2 (3)
C5—S1—C2	91.28 (15)	C12—C7—C6	119.8 (3)
N1—C1—C2	122.4 (3)	C8—C7—C6	121.0 (2)
N1—C1—H1A	118.8	C9—C8—C7	120.7 (3)
C2—C1—H1A	118.8	C9—C8—H8	119.6
C3—C2—C1	127.3 (3)	C7—C8—H8	119.6
C3—C2—S1	110.9 (2)	C8—C9—C10	120.0 (3)
C1—C2—S1	121.8 (2)	C8—C9—H9	120.0
C2—C3—C4	113.0 (3)	C10—C9—H9	120.0
C2—C3—H3	123.5	C11—C10—C9	119.0 (3)
C4—C3—H3	123.5	C11—C10—N1	117.8 (2)
C5—C4—C3	112.4 (3)	C9—C10—N1	123.0 (3)
C5—C4—H4	123.8	C12—C11—C10	120.9 (3)
C3—C4—H4	123.8	C12—C11—H11	119.5
C4—C5—S1	112.4 (2)	C10—C11—H11	119.5
C4—C5—H5	123.8	C11—C12—C7	120.1 (3)
S1—C5—H5	123.8	C11—C12—H12	120.0
O2—C6—O1	123.0 (3)	C7—C12—H12	120.0
O2—C6—C7	120.1 (3)
C10—N1—C1—C2	−176.1 (3)	O1—C6—C7—C8	1.8 (4)
N1—C1—C2—C3	179.9 (3)	C12—C7—C8—C9	1.2 (5)
N1—C1—C2—S1	1.4 (4)	C6—C7—C8—C9	−175.6 (3)
C5—S1—C2—C3	−0.4 (3)	C7—C8—C9—C10	−0.4 (5)
C5—S1—C2—C1	178.3 (3)	C8—C9—C10—C11	−0.1 (4)
C1—C2—C3—C4	−178.4 (3)	C8—C9—C10—N1	175.2 (3)
S1—C2—C3—C4	0.2 (4)	C1—N1—C10—C11	−143.8 (3)
C2—C3—C4—C5	0.2 (4)	C1—N1—C10—C9	40.8 (4)
C3—C4—C5—S1	−0.5 (4)	C9—C10—C11—C12	−0.1 (5)
C2—S1—C5—C4	0.5 (3)	N1—C10—C11—C12	−175.7 (3)
O2—C6—C7—C12	4.9 (4)	C10—C11—C12—C7	0.9 (5)
O1—C6—C7—C12	−175.0 (3)	C8—C7—C12—C11	−1.5 (5)
O2—C6—C7—C8	−178.2 (3)	C6—C7—C12—C11	175.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.83	2.641 (3)	172
C3—H3···O2ii	0.93	2.52	3.441 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.83	2.641 (3)	172
C3—H3⋯O2ii	0.93	2.52	3.441 (4)	169

Symmetry codes: (i) ; (ii) .