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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1159.
Published online 2008 May 30. doi:  10.1107/S1600536808015407
PMCID: PMC2961500

(E)-4-[(2-Hydroxy­benzyl­idene)amino]benzene­sulfonic acid

Abstract

The title mol­ecule, C13H11NO4S, 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 intra­molecular O—H(...)N hydrogen bond and mol­ecules 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 [triangle]).

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Object name is e-64-o1159-scheme1.jpg

Experimental

Crystal data

  • C13H11NO4S
  • M r = 277.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1159-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 822 Friedel pairs
  • Flack parameter: −0.06 (14)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors are grateful for research grant No. 02js40 from the Phytochemistry Key Laboratory of Shaanxi Province.

supplementary crystallographic information

Comment

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. As an extension of the work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

The structure of the title molecule is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The C7?N1 bond length of 1.262 (7) Å conforms to the value for a double bond. The dihedral angle between C1—C6 and C8—C13 benzene rings is 23.3 (5)° and that between C1/C2'/C3'/C4/C5'/C6' and C8—C13 rings is 18.3 (5)°. The C7—N1—C4—C5, C7—N1—C4—C3, O1—S1—C1—C6, O3—S1—C1—C6 and O2—S1—C1—C6 torsion angles are 22.8 (12)°, -156.4 (9)°, 173.5 (9)°, -58.9 (9)° and 56.3 (9)°, respectively. The molecule adopts a trans configuration about the C7?N1 bond. There exists an intramolecular O4—H4···N1 hydrogen bond involving the hydroxyl group and the imine N atom (Table 1).

In the crystal structure, the molecules are linked into chains running along the a axis by O—H···O hydrogen bonds.

Experimental

Salicylaldehyde (0.1 mmol, 12.2 mg) and sulfamide (0.1 mmol, 17.2 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min and then filtered. The filtrate was allowed to stand in air for 3 d, after which time yellow block-shaped crystals of the title compound were formed by slow evaporation of the solvent. The crystals were collected, washed with methanol and dried in a vacuum desiccator using anhydrous CaCl2 (yield 54%). Analysis found: C 48.88, H 3.20, N 4.07%; calculated for C13H11NO4S: C 48.9, H 3.20, N 4.08%.

Refinement

The central benzene ring is disordered over two orientations (C1—C6/C1,C2',C3',C4,C5',C6') with refined occupancies of 0.510 (16) and 0.490 (16). The –OH group is also disordered over two positions with refined occupancies of 0.528 (8) and 0.472 (8). H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with O—H = 0.82 Å, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Both disorder components are shown.

Crystal data

C13H11NO4SF000 = 576
Mr = 277.29Dx = 1.453 Mg m3
Monoclinic, CcMo Kα radiation λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1329 reflections
a = 4.8711 (5) Åθ = 2.7–23.9º
b = 29.022 (3) ŵ = 0.27 mm1
c = 9.0356 (17) ÅT = 298 (2) K
β = 97.223 (2)ºBlock, yellow
V = 1267.2 (3) Å30.42 × 0.31 × 0.15 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer1952 independent reflections
Radiation source: fine-focus sealed tube1656 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −5→5
Tmin = 0.897, Tmax = 0.961k = −34→31
3185 measured reflectionsl = −9→10

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.09Δρmax = 0.34 e Å3
1952 reflectionsΔρmin = −0.30 e Å3
213 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 822 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.06 (14)
Secondary atom site location: difference Fourier map

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S10.75870 (18)0.76105 (3)0.47671 (13)0.0372 (3)
N10.6129 (9)0.96320 (13)0.4070 (4)0.0490 (10)
O10.6035 (6)0.73963 (10)0.3515 (3)0.0470 (8)
O20.6306 (8)0.74475 (13)0.6247 (5)0.0663 (11)
H20.46780.75260.61850.099*
O31.0490 (7)0.75204 (11)0.5021 (4)0.0501 (8)
O40.387 (2)1.0337 (3)0.2463 (11)0.0675 (18)0.528 (8)
H40.45791.00800.24830.101*0.528 (8)
O4'0.285 (2)1.0279 (4)0.3133 (12)0.0675 (18)0.472 (8)
H4'0.31381.00310.35570.101*0.472 (8)
C10.7196 (9)0.82135 (14)0.4573 (5)0.0365 (11)
C20.585 (3)0.8377 (3)0.3264 (16)0.042 (3)0.510 (16)
H2A0.51780.81790.24930.051*0.510 (16)
C30.554 (3)0.8837 (3)0.3133 (16)0.045 (3)0.510 (16)
H30.45980.89550.22540.055*0.510 (16)
C2'0.470 (3)0.8413 (3)0.3925 (16)0.042 (3)0.490 (16)
H2'0.32240.82230.35860.051*0.490 (16)
C3'0.439 (3)0.8887 (3)0.3777 (16)0.044 (3)0.490 (16)
H3'0.27330.90150.33390.053*0.490 (16)
C40.6589 (11)0.91570 (17)0.4298 (6)0.0426 (11)
C50.805 (3)0.8949 (4)0.5579 (16)0.046 (3)0.510 (16)
H50.88680.91360.63460.056*0.510 (16)
C60.829 (3)0.8473 (4)0.5726 (16)0.043 (3)0.510 (16)
H60.91790.83390.65920.052*0.510 (16)
C5'0.909 (3)0.8993 (4)0.4909 (19)0.047 (3)0.490 (16)
H5'1.05470.91930.52130.056*0.490 (16)
C6'0.941 (3)0.8522 (4)0.5065 (17)0.047 (3)0.490 (16)
H6'1.11000.84030.54970.057*0.490 (16)
C70.7682 (15)0.99282 (16)0.4771 (9)0.0655 (13)
H70.91800.98260.54290.079*
C80.7245 (14)1.04208 (16)0.4601 (8)0.0570 (14)
C90.5144 (14)1.0594 (2)0.3606 (8)0.0771 (19)
C100.488 (2)1.1068 (2)0.3501 (10)0.107 (3)
H100.34371.11870.28430.129*
C110.6584 (18)1.1363 (2)0.4287 (9)0.0768 (18)
H110.63211.16790.41720.092*
C120.863 (2)1.1202 (2)0.5224 (11)0.102 (3)
H120.98401.14040.57760.122*
C130.8992 (19)1.0729 (2)0.5393 (10)0.111 (3)
H131.04551.06180.60590.133*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0310 (6)0.0410 (5)0.0369 (5)0.0050 (6)−0.0055 (4)−0.0024 (6)
N10.052 (3)0.041 (2)0.054 (3)−0.0006 (18)0.008 (2)0.0014 (18)
O10.048 (2)0.0473 (18)0.0402 (19)0.0021 (15)−0.0139 (15)−0.0081 (15)
O20.055 (2)0.072 (2)0.070 (3)0.0037 (18)0.0028 (19)0.0086 (19)
O30.0328 (18)0.057 (2)0.060 (2)0.0086 (14)0.0027 (15)−0.0050 (16)
O40.076 (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)
C10.032 (3)0.040 (2)0.037 (3)0.002 (2)0.003 (2)0.000 (2)
C20.047 (8)0.039 (6)0.039 (7)−0.008 (5)−0.001 (6)−0.005 (5)
C30.047 (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)
C40.041 (3)0.040 (3)0.046 (3)−0.002 (2)0.005 (2)−0.001 (2)
C50.057 (9)0.041 (6)0.042 (7)0.002 (5)0.007 (6)−0.008 (5)
C60.048 (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)
C70.069 (3)0.048 (3)0.075 (3)−0.001 (4)−0.010 (3)0.009 (4)
C80.064 (4)0.042 (2)0.066 (4)−0.006 (3)0.013 (3)0.002 (3)
C90.083 (5)0.051 (3)0.091 (5)0.019 (3)−0.014 (4)−0.018 (3)
C100.125 (7)0.058 (4)0.126 (7)0.030 (4)−0.035 (6)−0.003 (4)
C110.105 (6)0.046 (3)0.084 (5)0.006 (4)0.027 (4)−0.004 (3)
C120.118 (7)0.056 (4)0.125 (7)−0.021 (5)−0.012 (6)0.001 (5)
C130.120 (6)0.058 (4)0.139 (7)−0.013 (4)−0.042 (6)0.010 (5)

Geometric parameters (Å, °)

S1—O11.422 (3)C3'—H3'0.93
S1—O31.428 (3)C4—C5'1.359 (15)
S1—O21.615 (4)C4—C51.415 (14)
S1—C11.767 (4)C5—C61.392 (15)
N1—C71.262 (7)C5—H50.93
N1—C41.408 (6)C6—H60.93
O2—H20.82C5'—C6'1.382 (15)
O4—C91.359 (10)C5'—H5'0.93
O4—H40.82C6'—H6'0.93
O4'—C91.465 (12)C7—C81.451 (6)
O4'—H4'0.82C7—H70.93
C1—C61.340 (11)C8—C91.370 (8)
C1—C21.363 (12)C8—C131.372 (9)
C1—C2'1.405 (12)C9—C101.382 (8)
C1—C6'1.430 (13)C10—C111.333 (11)
C2—C31.348 (13)C10—H100.93
C2—H2A0.93C11—C121.310 (10)
C3—C41.448 (13)C11—H110.93
C3—H30.93C12—C131.390 (9)
C2'—C3'1.387 (14)C12—H120.93
C2'—H2'0.93C13—H130.93
C3'—C41.364 (12)
O1—S1—O3117.6 (2)C5—C4—C3114.6 (7)
O1—S1—O2108.0 (2)C6—C5—C4122.0 (10)
O3—S1—O2106.9 (2)C6—C5—H5119.0
O1—S1—C1108.29 (19)C4—C5—H5119.0
O3—S1—C1106.8 (2)C1—C6—C5117.5 (10)
O2—S1—C1108.9 (2)C1—C6—H6121.2
C7—N1—C4121.3 (4)C5—C6—H6121.2
S1—O2—H2109.5C4—C5'—C6'118.2 (11)
C9—O4—H4109.5C4—C5'—H5'120.9
C9—O4'—H4'109.5C6'—C5'—H5'120.9
C6—C1—C2125.4 (8)C5'—C6'—C1121.1 (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—C8123.2 (6)
C6—C1—S1116.8 (6)N1—C7—H7118.4
C2—C1—S1117.7 (5)C8—C7—H7118.4
C2'—C1—S1121.8 (5)C9—C8—C13117.8 (6)
C6'—C1—S1121.4 (5)C9—C8—C7121.3 (6)
C3—C2—C1117.3 (10)C13—C8—C7120.9 (6)
C3—C2—H2A121.4O4—C9—C8121.9 (6)
C1—C2—H2A121.4O4—C9—C10117.7 (7)
C2—C3—C4123.0 (10)C8—C9—C10117.7 (6)
C2—C3—H3118.5C8—C9—O4'116.2 (6)
C4—C3—H3118.5C10—C9—O4'122.7 (7)
C3'—C2'—C1121.9 (9)C11—C10—C9123.8 (7)
C3'—C2'—H2'119.0C11—C10—H10118.1
C1—C2'—H2'119.0C9—C10—H10118.1
C4—C3'—C2'117.6 (10)C12—C11—C10119.1 (7)
C4—C3'—H3'121.2C12—C11—H11120.5
C2'—C3'—H3'121.2C10—C11—H11120.5
C5'—C4—C3'124.4 (8)C11—C12—C13119.9 (8)
C5'—C4—N1121.3 (6)C11—C12—H12120.0
C3'—C4—N1114.1 (6)C13—C12—H12120.0
C3'—C4—C5109.2 (8)C8—C13—C12121.7 (8)
N1—C4—C5126.3 (6)C8—C13—H13119.2
C5'—C4—C3106.8 (8)C12—C13—H13119.2
N1—C4—C3119.1 (6)
O1—S1—C1—C6173.5 (9)C3'—C4—C5—C634.7 (15)
O3—S1—C1—C6−58.9 (9)N1—C4—C5—C6177.2 (9)
O2—S1—C1—C656.3 (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—C2120.2 (8)C2'—C1—C6—C5−37.8 (14)
O2—S1—C1—C2−124.6 (8)C6'—C1—C6—C571.4 (15)
O1—S1—C1—C2'35.0 (9)S1—C1—C6—C5178.8 (9)
O3—S1—C1—C2'162.6 (8)C4—C5—C6—C13.0 (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'—C11(2)
C2'—C1—C2—C372.3 (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—C3179.3 (9)C2'—C1—C6'—C5'0.2 (17)
C1—C2—C3—C41.0 (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—C13179.9 (8)
S1—C1—C2'—C3'179.7 (9)C13—C8—C9—O4159.1 (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—N1178.4 (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—C371.5 (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—C111.4 (14)
C7—N1—C4—C522.8 (12)O4'—C9—C10—C11159.7 (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—C121.3 (13)
C2—C3—C4—N1−179.1 (10)C7—C8—C13—C12178.9 (9)
C2—C3—C4—C51.5 (17)C11—C12—C13—C8−0.2 (14)
C5'—C4—C5—C6−88.1 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O3i0.822.172.917 (5)151
O4—H4···N10.822.012.665 (10)136

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2596).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography