(E)-4-[(2-Hydroxy-benzyl-idene)amino]benzene-sulfonic acid.

The title mol-ecule, C(13)H(11)NO(4)S, displays a trans configuration with respect to the imine C=N double bond. The central benzene ring directly linked to N and the hydroxyl group are disordered over two orientations [occupancies of 0.510 (16)/0.490 (16) and 0.528 (8)/0.472 (8), respectively]. The dihedral angle between the two aromatic rings is 23.3 (5)° for the major component and 18.3 (5)° for the minor component. There is an intra-molecular O-H⋯N hydrogen bond and mol-ecules are linked into chains along the a axis by O-H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H11NO4S

M = 277.29

Monoclinic,

a = 4.8711 (5) Å

b = 29.022 (3) Å

c = 9.0356 (17) Å

β = 97.223 (2)°

V = 1267.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 298 (2) K

0.42 × 0.31 × 0.15 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.897, T max = 0.961

3185 measured reflections

1952 independent reflections

1656 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.121

S = 1.09

1952 reflections

213 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 822 Friedel pairs

Flack parameter: −0.06 (14)

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/S1600536808015407/ci2596sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015407/ci2596Isup2.hkl

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

C13H11NO4S	F000 = 576
Mr = 277.29	Dx = 1.453 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1329 reflections
a = 4.8711 (5) Å	θ = 2.7–23.9º
b = 29.022 (3) Å	µ = 0.27 mm−1
c = 9.0356 (17) Å	T = 298 (2) K
β = 97.223 (2)º	Block, yellow
V = 1267.2 (3) Å3	0.42 × 0.31 × 0.15 mm
Z = 4

Siemens SMART CCD area-detector diffractometer	1952 independent reflections
Radiation source: fine-focus sealed tube	1656 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.897, Tmax = 0.961	k = −34→31
3185 measured reflections	l = −9→10

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050	w = 1/[σ2(Fo2) + (0.0495P)2 + 1.7913P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.34 e Å−3
1952 reflections	Δρmin = −0.30 e Å−3
213 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 822 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (14)
Secondary atom site location: difference Fourier map

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	Occ. (<1)
S1	0.75870 (18)	0.76105 (3)	0.47671 (13)	0.0372 (3)
N1	0.6129 (9)	0.96320 (13)	0.4070 (4)	0.0490 (10)
O1	0.6035 (6)	0.73963 (10)	0.3515 (3)	0.0470 (8)
O2	0.6306 (8)	0.74475 (13)	0.6247 (5)	0.0663 (11)
H2	0.4678	0.7526	0.6185	0.099*
O3	1.0490 (7)	0.75204 (11)	0.5021 (4)	0.0501 (8)
O4	0.387 (2)	1.0337 (3)	0.2463 (11)	0.0675 (18)	0.528 (8)
H4	0.4579	1.0080	0.2483	0.101*	0.528 (8)
O4'	0.285 (2)	1.0279 (4)	0.3133 (12)	0.0675 (18)	0.472 (8)
H4'	0.3138	1.0031	0.3557	0.101*	0.472 (8)
C1	0.7196 (9)	0.82135 (14)	0.4573 (5)	0.0365 (11)
C2	0.585 (3)	0.8377 (3)	0.3264 (16)	0.042 (3)	0.510 (16)
H2A	0.5178	0.8179	0.2493	0.051*	0.510 (16)
C3	0.554 (3)	0.8837 (3)	0.3133 (16)	0.045 (3)	0.510 (16)
H3	0.4598	0.8955	0.2254	0.055*	0.510 (16)
C2'	0.470 (3)	0.8413 (3)	0.3925 (16)	0.042 (3)	0.490 (16)
H2'	0.3224	0.8223	0.3586	0.051*	0.490 (16)
C3'	0.439 (3)	0.8887 (3)	0.3777 (16)	0.044 (3)	0.490 (16)
H3'	0.2733	0.9015	0.3339	0.053*	0.490 (16)
C4	0.6589 (11)	0.91570 (17)	0.4298 (6)	0.0426 (11)
C5	0.805 (3)	0.8949 (4)	0.5579 (16)	0.046 (3)	0.510 (16)
H5	0.8868	0.9136	0.6346	0.056*	0.510 (16)
C6	0.829 (3)	0.8473 (4)	0.5726 (16)	0.043 (3)	0.510 (16)
H6	0.9179	0.8339	0.6592	0.052*	0.510 (16)
C5'	0.909 (3)	0.8993 (4)	0.4909 (19)	0.047 (3)	0.490 (16)
H5'	1.0547	0.9193	0.5213	0.056*	0.490 (16)
C6'	0.941 (3)	0.8522 (4)	0.5065 (17)	0.047 (3)	0.490 (16)
H6'	1.1100	0.8403	0.5497	0.057*	0.490 (16)
C7	0.7682 (15)	0.99282 (16)	0.4771 (9)	0.0655 (13)
H7	0.9180	0.9826	0.5429	0.079*
C8	0.7245 (14)	1.04208 (16)	0.4601 (8)	0.0570 (14)
C9	0.5144 (14)	1.0594 (2)	0.3606 (8)	0.0771 (19)
C10	0.488 (2)	1.1068 (2)	0.3501 (10)	0.107 (3)
H10	0.3437	1.1187	0.2843	0.129*
C11	0.6584 (18)	1.1363 (2)	0.4287 (9)	0.0768 (18)
H11	0.6321	1.1679	0.4172	0.092*
C12	0.863 (2)	1.1202 (2)	0.5224 (11)	0.102 (3)
H12	0.9840	1.1404	0.5776	0.122*
C13	0.8992 (19)	1.0729 (2)	0.5393 (10)	0.111 (3)
H13	1.0455	1.0618	0.6059	0.133*

	U11	U22	U33	U12	U13	U23
S1	0.0310 (6)	0.0410 (5)	0.0369 (5)	0.0050 (6)	−0.0055 (4)	−0.0024 (6)
N1	0.052 (3)	0.041 (2)	0.054 (3)	−0.0006 (18)	0.008 (2)	0.0014 (18)
O1	0.048 (2)	0.0473 (18)	0.0402 (19)	0.0021 (15)	−0.0139 (15)	−0.0081 (15)
O2	0.055 (2)	0.072 (2)	0.070 (3)	0.0037 (18)	0.0028 (19)	0.0086 (19)
O3	0.0328 (18)	0.057 (2)	0.060 (2)	0.0086 (14)	0.0027 (15)	−0.0050 (16)
O4	0.076 (6)	0.062 (3)	0.062 (5)	0.009 (3)	−0.001 (3)	0.008 (4)
O4'	0.076 (6)	0.062 (3)	0.062 (5)	0.009 (3)	−0.001 (3)	0.008 (4)
C1	0.032 (3)	0.040 (2)	0.037 (3)	0.002 (2)	0.003 (2)	0.000 (2)
C2	0.047 (8)	0.039 (6)	0.039 (7)	−0.008 (5)	−0.001 (6)	−0.005 (5)
C3	0.047 (7)	0.045 (6)	0.043 (7)	0.002 (5)	0.001 (6)	0.002 (5)
C2'	0.036 (7)	0.041 (6)	0.047 (8)	−0.004 (5)	−0.004 (6)	−0.004 (5)
C3'	0.044 (7)	0.042 (6)	0.046 (7)	0.005 (5)	0.004 (6)	0.000 (5)
C4	0.041 (3)	0.040 (3)	0.046 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
C5	0.057 (9)	0.041 (6)	0.042 (7)	0.002 (5)	0.007 (6)	−0.008 (5)
C6	0.048 (8)	0.042 (6)	0.036 (7)	0.002 (5)	−0.003 (6)	−0.007 (5)
C5'	0.041 (8)	0.042 (6)	0.056 (9)	−0.003 (5)	0.004 (7)	−0.008 (6)
C6'	0.037 (8)	0.046 (7)	0.057 (9)	0.003 (5)	0.000 (7)	−0.003 (6)
C7	0.069 (3)	0.048 (3)	0.075 (3)	−0.001 (4)	−0.010 (3)	0.009 (4)
C8	0.064 (4)	0.042 (2)	0.066 (4)	−0.006 (3)	0.013 (3)	0.002 (3)
C9	0.083 (5)	0.051 (3)	0.091 (5)	0.019 (3)	−0.014 (4)	−0.018 (3)
C10	0.125 (7)	0.058 (4)	0.126 (7)	0.030 (4)	−0.035 (6)	−0.003 (4)
C11	0.105 (6)	0.046 (3)	0.084 (5)	0.006 (4)	0.027 (4)	−0.004 (3)
C12	0.118 (7)	0.056 (4)	0.125 (7)	−0.021 (5)	−0.012 (6)	0.001 (5)
C13	0.120 (6)	0.058 (4)	0.139 (7)	−0.013 (4)	−0.042 (6)	0.010 (5)

S1—O1	1.422 (3)	C3'—H3'	0.93
S1—O3	1.428 (3)	C4—C5'	1.359 (15)
S1—O2	1.615 (4)	C4—C5	1.415 (14)
S1—C1	1.767 (4)	C5—C6	1.392 (15)
N1—C7	1.262 (7)	C5—H5	0.93
N1—C4	1.408 (6)	C6—H6	0.93
O2—H2	0.82	C5'—C6'	1.382 (15)
O4—C9	1.359 (10)	C5'—H5'	0.93
O4—H4	0.82	C6'—H6'	0.93
O4'—C9	1.465 (12)	C7—C8	1.451 (6)
O4'—H4'	0.82	C7—H7	0.93
C1—C6	1.340 (11)	C8—C9	1.370 (8)
C1—C2	1.363 (12)	C8—C13	1.372 (9)
C1—C2'	1.405 (12)	C9—C10	1.382 (8)
C1—C6'	1.430 (13)	C10—C11	1.333 (11)
C2—C3	1.348 (13)	C10—H10	0.93
C2—H2A	0.93	C11—C12	1.310 (10)
C3—C4	1.448 (13)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.390 (9)
C2'—C3'	1.387 (14)	C12—H12	0.93
C2'—H2'	0.93	C13—H13	0.93
C3'—C4	1.364 (12)
O1—S1—O3	117.6 (2)	C5—C4—C3	114.6 (7)
O1—S1—O2	108.0 (2)	C6—C5—C4	122.0 (10)
O3—S1—O2	106.9 (2)	C6—C5—H5	119.0
O1—S1—C1	108.29 (19)	C4—C5—H5	119.0
O3—S1—C1	106.8 (2)	C1—C6—C5	117.5 (10)
O2—S1—C1	108.9 (2)	C1—C6—H6	121.2
C7—N1—C4	121.3 (4)	C5—C6—H6	121.2
S1—O2—H2	109.5	C4—C5'—C6'	118.2 (11)
C9—O4—H4	109.5	C4—C5'—H5'	120.9
C9—O4'—H4'	109.5	C6'—C5'—H5'	120.9
C6—C1—C2	125.4 (8)	C5'—C6'—C1	121.1 (11)
C6—C1—C2'	109.3 (8)	C5'—C6'—H6'	119.5
C2—C1—C6'	108.3 (7)	C1—C6'—H6'	119.5
C2'—C1—C6'	116.8 (7)	N1—C7—C8	123.2 (6)
C6—C1—S1	116.8 (6)	N1—C7—H7	118.4
C2—C1—S1	117.7 (5)	C8—C7—H7	118.4
C2'—C1—S1	121.8 (5)	C9—C8—C13	117.8 (6)
C6'—C1—S1	121.4 (5)	C9—C8—C7	121.3 (6)
C3—C2—C1	117.3 (10)	C13—C8—C7	120.9 (6)
C3—C2—H2A	121.4	O4—C9—C8	121.9 (6)
C1—C2—H2A	121.4	O4—C9—C10	117.7 (7)
C2—C3—C4	123.0 (10)	C8—C9—C10	117.7 (6)
C2—C3—H3	118.5	C8—C9—O4'	116.2 (6)
C4—C3—H3	118.5	C10—C9—O4'	122.7 (7)
C3'—C2'—C1	121.9 (9)	C11—C10—C9	123.8 (7)
C3'—C2'—H2'	119.0	C11—C10—H10	118.1
C1—C2'—H2'	119.0	C9—C10—H10	118.1
C4—C3'—C2'	117.6 (10)	C12—C11—C10	119.1 (7)
C4—C3'—H3'	121.2	C12—C11—H11	120.5
C2'—C3'—H3'	121.2	C10—C11—H11	120.5
C5'—C4—C3'	124.4 (8)	C11—C12—C13	119.9 (8)
C5'—C4—N1	121.3 (6)	C11—C12—H12	120.0
C3'—C4—N1	114.1 (6)	C13—C12—H12	120.0
C3'—C4—C5	109.2 (8)	C8—C13—C12	121.7 (8)
N1—C4—C5	126.3 (6)	C8—C13—H13	119.2
C5'—C4—C3	106.8 (8)	C12—C13—H13	119.2
N1—C4—C3	119.1 (6)
O1—S1—C1—C6	173.5 (9)	C3'—C4—C5—C6	34.7 (15)
O3—S1—C1—C6	−58.9 (9)	N1—C4—C5—C6	177.2 (9)
O2—S1—C1—C6	56.3 (9)	C3—C4—C5—C6	−3.6 (16)
O1—S1—C1—C2	−7.4 (9)	C2—C1—C6—C5	−0.2 (17)
O3—S1—C1—C2	120.2 (8)	C2'—C1—C6—C5	−37.8 (14)
O2—S1—C1—C2	−124.6 (8)	C6'—C1—C6—C5	71.4 (15)
O1—S1—C1—C2'	35.0 (9)	S1—C1—C6—C5	178.8 (9)
O3—S1—C1—C2'	162.6 (8)	C4—C5—C6—C1	3.0 (18)
O2—S1—C1—C2'	−82.2 (9)	C3'—C4—C5'—C6'	−2.4 (19)
O1—S1—C1—C6'	−144.8 (9)	N1—C4—C5'—C6'	−178.4 (10)
O3—S1—C1—C6'	−17.2 (9)	C5—C4—C5'—C6'	71.8 (15)
O2—S1—C1—C6'	98.0 (9)	C3—C4—C5'—C6'	−37.3 (15)
C6—C1—C2—C3	−1.7 (17)	C4—C5'—C6'—C1	1(2)
C2'—C1—C2—C3	72.3 (14)	C6—C1—C6'—C5'	−86.4 (17)
C6'—C1—C2—C3	−38.2 (14)	C2—C1—C6'—C5'	39.1 (16)
S1—C1—C2—C3	179.3 (9)	C2'—C1—C6'—C5'	0.2 (17)
C1—C2—C3—C4	1.0 (18)	S1—C1—C6'—C5'	180.0 (10)
C6—C1—C2'—C3'	38.5 (15)	C4—N1—C7—C8	−178.4 (6)
C2—C1—C2'—C3'	−85.4 (15)	N1—C7—C8—C9	−2.7 (11)
C6'—C1—C2'—C3'	−0.5 (16)	N1—C7—C8—C13	179.9 (8)
S1—C1—C2'—C3'	179.7 (9)	C13—C8—C9—O4	159.1 (9)
C1—C2'—C3'—C4	−0.6 (17)	C7—C8—C9—O4	−18.5 (11)
C2'—C3'—C4—C5'	2.1 (17)	C13—C8—C9—C10	−1.8 (11)
C2'—C3'—C4—N1	178.4 (9)	C7—C8—C9—C10	−179.4 (8)
C2'—C3'—C4—C5	−34.2 (14)	C13—C8—C9—O4'	−161.6 (8)
C2'—C3'—C4—C3	71.5 (13)	C7—C8—C9—O4'	20.9 (11)
C7—N1—C4—C5'	−19.9 (12)	O4—C9—C10—C11	−160.3 (10)
C7—N1—C4—C3'	163.7 (9)	C8—C9—C10—C11	1.4 (14)
C7—N1—C4—C5	22.8 (12)	O4'—C9—C10—C11	159.7 (10)
C7—N1—C4—C3	−156.4 (9)	C9—C10—C11—C12	−0.2 (15)
C2—C3—C4—C5'	38.7 (16)	C10—C11—C12—C13	−0.4 (14)
C2—C3—C4—C3'	−87.5 (16)	C9—C8—C13—C12	1.3 (13)
C2—C3—C4—N1	−179.1 (10)	C7—C8—C13—C12	178.9 (9)
C2—C3—C4—C5	1.5 (17)	C11—C12—C13—C8	−0.2 (14)
C5'—C4—C5—C6	−88.1 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	2.17	2.917 (5)	151
O4—H4···N1	0.82	2.01	2.665 (10)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.82	2.17	2.917 (5)	151
O4—H4⋯N1	0.82	2.01	2.665 (10)	136

Symmetry code: (i) .