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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2339.
Published online 2009 September 5. doi:  10.1107/S1600536809035090
PMCID: PMC2970384

4-(4-Diethyl­amino-2-hydroxy­benzyl­idene­ammonio)-3-methyl­benzene­sulfonate dihydrate

Abstract

In the crystal of the title compound, C18H22N2O4S·2H2O, mol­ecules are linked into a one-dimensional chain structure by C—H(...)O, N—H(...)O, O—H(...)O and O—H(...)N hydrogen bonds.

Related literature

For the biological and pharmacological activities of Schiff base compounds, see: Bu et al. (2001 [triangle]); Ranford et al. (1998 [triangle]).

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Object name is e-65-o2339-scheme1.jpg

Experimental

Crystal data

  • C18H22N2O4S·2H2O
  • M r = 398.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2339-efi1.jpg
  • a = 21.690 (3) Å
  • b = 11.4142 (17) Å
  • c = 16.639 (2) Å
  • β = 112.459 (2)°
  • V = 3806.9 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 273 K
  • 0.19 × 0.16 × 0.06 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.962, T max = 0.988
  • 9821 measured reflections
  • 3379 independent reflections
  • 2910 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.171
  • S = 1.05
  • 3379 reflections
  • 246 parameters
  • H-atom parameters constrained
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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 global, I. DOI: 10.1107/S1600536809035090/at2871sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035090/at2871Isup2.hkl

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

Acknowledgments

The authors thank the Program for New Century Excellent Talents in Universities for a research grant.

supplementary crystallographic information

Comment

Schiff bases play an important role in the field of bioinorganic chemistry because they have remarkable wide biological and pharmacological activities, such as antitumor, antidiabetic, antitubercular activities [Ranford, et al., 1998; Bu, et al., 2001]. Therefore, investigating the synthesis and proper ties of hydrazone of these compounds seems to be a very interesting problem. as one part of our systematic work, In this paper, we report on the synthesis and crystal structure of the title compound, (I), (Fig. 1).

The dihedral angle between the aromatic ring planes (C1–C6) and (C9–C14) is 5.70 (12)°, showing that the whole compound is not a plane molecule. The bond distances of C8—N1 [1.311 (3) Å], S1—O2 [1.449 (2) Å] and S1—O3 [1.426 (3) Å] are consistent with the carbon-nitrogen and sulfur-oxygen double-bond lengths, respectively. In the crystal packing, the molecules form a one-dimensional chain structure by C—H···O, N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1).

Experimental

The solution of 1.0 mmol 4-(diethylamino)salicylaldehyde was added to a solution of 1.0 mmol 3-methyl-benzenesulfonic acid in 5 ml ethanol at room temperature. The mixture was refluxed for 4 h with stirring, then the resulting precipitate was filtered, washed, and dried in vacuo over P4O10 for 48 h. Single crystals suitable for X-ray structural analysis was obtained by slowly evaporating from methanol at room temperature.

Refinement

All H atoms were included in the refinement at calculated positions, in the riding-model approximation, with C–H distances of 0.93 (ArH), 0.98 (CH3), 0.97Å (CH2), N–H = 0.86 Å (NH), O–H = 0.82 Å (OH) and 0.85 Å (H2O) . The isotropic displacement parameters for all H atoms were set equal to 1.2 or 1.5Ueq of the carrier atom.

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids.

Crystal data

C18H22N2O4S·2H2OF(000) = 1696
Mr = 398.47Dx = 1.390 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4718 reflections
a = 21.690 (3) Åθ = 2.2–28.4°
b = 11.4142 (17) ŵ = 0.21 mm1
c = 16.639 (2) ÅT = 273 K
β = 112.459 (2)°Block, colourless
V = 3806.9 (9) Å30.19 × 0.16 × 0.06 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer3379 independent reflections
Radiation source: fine-focus sealed tube2910 reflections with I > 2σ(I)
graphiteRint = 0.026
[var phi] and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→25
Tmin = 0.962, Tmax = 0.988k = −13→13
9821 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.171w = 1/[σ2(Fo2) + (0.1015P)2 + 5.082P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3379 reflectionsΔρmax = 0.73 e Å3
246 parametersΔρmin = −0.41 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (5)

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*/Ueq
S10.18156 (3)0.09473 (5)−0.21298 (4)0.0405 (3)
O10.17722 (12)0.1276 (2)−0.29916 (14)0.0750 (8)
O20.11837 (9)0.1127 (2)−0.20400 (13)0.0573 (6)
O30.20786 (13)−0.0203 (2)−0.1892 (2)0.0980 (11)
O40.18994 (19)0.6795 (4)0.0958 (2)0.1365 (14)
H160.22520.64200.12540.205*
H150.16300.66690.12090.205*
O50.276 (2)0.6202 (16)1.001 (2)0.81 (3)
H180.30310.56641.00161.213*
H170.25820.64260.94871.213*
O60.50747 (8)0.45092 (15)0.15864 (11)0.0392 (4)
H60.53920.44050.20470.059*
N10.39104 (9)0.41470 (17)0.02004 (12)0.0332 (5)
H10.41540.38910.07090.040*
N20.60480 (10)0.83477 (18)0.19161 (14)0.0404 (5)
C10.24039 (11)0.1925 (2)−0.13942 (15)0.0343 (5)
C20.28796 (12)0.1511 (2)−0.06245 (15)0.0345 (5)
H20.28630.0733−0.04680.041*
C30.33840 (11)0.2239 (2)−0.00783 (14)0.0306 (5)
C40.33861 (11)0.3409 (2)−0.03262 (14)0.0303 (5)
C50.28903 (12)0.3837 (2)−0.10848 (16)0.0387 (6)
H50.28860.4624−0.12300.046*
C60.24063 (12)0.3090 (2)−0.16183 (16)0.0412 (6)
H6A0.20810.3371−0.21290.049*
C70.39164 (13)0.1746 (2)0.07302 (16)0.0442 (6)
H7A0.38370.09250.07740.066*
H7B0.39050.21450.12320.066*
H7C0.43460.18530.07000.066*
C80.40592 (11)0.5183 (2)−0.00150 (15)0.0338 (5)
H80.37900.5459−0.05630.041*
C90.45786 (11)0.59191 (19)0.04893 (15)0.0322 (5)
C100.50910 (11)0.5615 (2)0.13088 (14)0.0304 (5)
C110.55669 (11)0.6412 (2)0.17671 (15)0.0343 (5)
H110.58910.61940.22990.041*
C120.55782 (11)0.7562 (2)0.14517 (16)0.0355 (5)
C130.50789 (13)0.7859 (2)0.06268 (17)0.0417 (6)
H130.50730.86050.04000.050*
C140.46131 (13)0.7060 (2)0.01705 (16)0.0412 (6)
H140.43030.7270−0.03740.049*
C150.65369 (14)0.8065 (3)0.27868 (18)0.0514 (7)
H15A0.69120.85980.29290.062*
H15B0.67020.72770.27820.062*
C160.6252 (3)0.8148 (4)0.3481 (2)0.0935 (13)
H16A0.58240.77710.32820.140*
H16B0.62030.89570.36030.140*
H16C0.65470.77680.40000.140*
C170.60749 (14)0.9541 (2)0.1600 (2)0.0490 (7)
H17A0.59440.95160.09730.059*
H17B0.65320.98180.18500.059*
C180.56346 (19)1.0404 (3)0.1815 (3)0.0720 (10)
H18A0.57911.04990.24340.108*
H18B0.51851.01160.15980.108*
H18C0.56481.11450.15490.108*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0310 (4)0.0404 (4)0.0444 (4)−0.0065 (2)0.0080 (3)−0.0132 (3)
O10.0836 (16)0.1016 (18)0.0462 (12)−0.0473 (14)0.0318 (12)−0.0338 (12)
O20.0341 (10)0.0851 (15)0.0515 (11)−0.0193 (9)0.0150 (8)−0.0287 (10)
O30.0664 (15)0.0437 (13)0.128 (2)0.0007 (11)−0.0253 (15)−0.0222 (14)
O40.102 (3)0.148 (3)0.120 (3)0.026 (2)−0.002 (2)0.010 (2)
O51.22 (7)0.36 (2)1.12 (5)−0.11 (3)0.75 (6)−0.22 (3)
O60.0317 (9)0.0359 (9)0.0378 (9)−0.0044 (7)−0.0004 (7)0.0086 (7)
N10.0283 (10)0.0372 (11)0.0262 (10)−0.0048 (8)0.0018 (8)0.0015 (8)
N20.0344 (11)0.0346 (11)0.0480 (12)−0.0076 (9)0.0112 (9)−0.0070 (9)
C10.0255 (11)0.0394 (13)0.0366 (12)−0.0036 (9)0.0101 (10)−0.0069 (10)
C20.0353 (12)0.0305 (12)0.0386 (13)−0.0035 (9)0.0150 (10)−0.0023 (9)
C30.0296 (11)0.0340 (12)0.0279 (11)0.0010 (9)0.0106 (9)0.0014 (9)
C40.0271 (11)0.0359 (12)0.0266 (11)−0.0046 (9)0.0087 (9)−0.0020 (9)
C50.0355 (13)0.0324 (12)0.0380 (13)−0.0030 (10)0.0027 (10)0.0054 (10)
C60.0332 (13)0.0428 (14)0.0363 (13)−0.0028 (10)0.0005 (10)0.0015 (10)
C70.0459 (15)0.0393 (14)0.0376 (13)0.0019 (11)0.0049 (11)0.0055 (10)
C80.0305 (12)0.0382 (13)0.0284 (11)−0.0007 (9)0.0066 (9)0.0026 (9)
C90.0278 (12)0.0349 (12)0.0304 (12)−0.0024 (9)0.0073 (9)0.0012 (9)
C100.0269 (11)0.0323 (11)0.0304 (11)−0.0003 (9)0.0091 (9)0.0022 (9)
C110.0279 (11)0.0361 (12)0.0332 (12)0.0001 (9)0.0053 (9)0.0001 (9)
C120.0309 (12)0.0356 (13)0.0417 (13)−0.0022 (10)0.0157 (10)−0.0053 (10)
C130.0430 (14)0.0343 (13)0.0427 (14)−0.0049 (10)0.0105 (11)0.0065 (10)
C140.0394 (14)0.0411 (14)0.0354 (13)−0.0014 (10)0.0056 (11)0.0078 (10)
C150.0443 (16)0.0477 (16)0.0514 (16)−0.0131 (12)0.0061 (13)−0.0089 (12)
C160.137 (4)0.091 (3)0.053 (2)0.004 (3)0.038 (2)−0.004 (2)
C170.0440 (15)0.0393 (14)0.0621 (17)−0.0096 (12)0.0185 (13)−0.0068 (13)
C180.072 (2)0.0533 (19)0.089 (3)0.0109 (17)0.0290 (19)−0.0022 (17)

Geometric parameters (Å, °)

S1—O31.426 (2)C7—H7A0.9600
S1—O21.449 (2)C7—H7B0.9600
S1—O11.450 (2)C7—H7C0.9600
S1—C11.783 (2)C8—C91.399 (3)
O4—H160.8502C8—H80.9300
O4—H150.8505C9—C141.419 (3)
O5—H180.8491C9—C101.434 (3)
O5—H170.8505C10—C111.369 (3)
O6—C101.349 (3)C11—C121.417 (3)
O6—H60.8200C11—H110.9300
N1—C81.311 (3)C12—C131.427 (3)
N1—C41.417 (3)C13—C141.357 (3)
N1—H10.8600C13—H130.9300
N2—C121.356 (3)C14—H140.9300
N2—C151.467 (3)C15—C161.507 (5)
N2—C171.470 (3)C15—H15A0.9700
C1—C61.382 (4)C15—H15B0.9700
C1—C21.385 (3)C16—H16A0.9600
C2—C31.398 (3)C16—H16B0.9600
C2—H20.9300C16—H16C0.9600
C3—C41.399 (3)C17—C181.506 (4)
C3—C71.508 (3)C17—H17A0.9700
C4—C51.397 (3)C17—H17B0.9700
C5—C61.380 (3)C18—H18A0.9600
C5—H50.9300C18—H18B0.9600
C6—H6A0.9300C18—H18C0.9600
O3—S1—O2113.29 (17)C8—C9—C14118.2 (2)
O3—S1—O1112.40 (19)C8—C9—C10125.4 (2)
O2—S1—O1111.02 (14)C14—C9—C10116.4 (2)
O3—S1—C1106.26 (12)O6—C10—C11123.0 (2)
O2—S1—C1107.32 (11)O6—C10—C9116.08 (19)
O1—S1—C1106.02 (12)C11—C10—C9121.0 (2)
H16—O4—H15105.3C10—C11—C12121.7 (2)
H18—O5—H17105.4C10—C11—H11119.1
C10—O6—H6109.5C12—C11—H11119.1
C8—N1—C4126.16 (19)N2—C12—C11121.1 (2)
C8—N1—H1116.9N2—C12—C13121.4 (2)
C4—N1—H1116.9C11—C12—C13117.5 (2)
C12—N2—C15121.3 (2)C14—C13—C12120.5 (2)
C12—N2—C17122.2 (2)C14—C13—H13119.7
C15—N2—C17116.4 (2)C12—C13—H13119.7
C6—C1—C2120.0 (2)C13—C14—C9122.8 (2)
C6—C1—S1119.52 (18)C13—C14—H14118.6
C2—C1—S1120.39 (18)C9—C14—H14118.6
C1—C2—C3121.3 (2)N2—C15—C16112.9 (3)
C1—C2—H2119.3N2—C15—H15A109.0
C3—C2—H2119.3C16—C15—H15A109.0
C2—C3—C4117.8 (2)N2—C15—H15B109.0
C2—C3—C7120.1 (2)C16—C15—H15B109.0
C4—C3—C7122.1 (2)H15A—C15—H15B107.8
C5—C4—C3120.8 (2)C15—C16—H16A109.5
C5—C4—N1120.7 (2)C15—C16—H16B109.5
C3—C4—N1118.52 (19)H16A—C16—H16B109.5
C6—C5—C4119.9 (2)C15—C16—H16C109.5
C6—C5—H5120.0H16A—C16—H16C109.5
C4—C5—H5120.0H16B—C16—H16C109.5
C5—C6—C1120.1 (2)N2—C17—C18113.9 (3)
C5—C6—H6A120.0N2—C17—H17A108.8
C1—C6—H6A120.0C18—C17—H17A108.8
C3—C7—H7A109.5N2—C17—H17B108.8
C3—C7—H7B109.5C18—C17—H17B108.8
H7A—C7—H7B109.5H17A—C17—H17B107.7
C3—C7—H7C109.5C17—C18—H18A109.5
H7A—C7—H7C109.5C17—C18—H18B109.5
H7B—C7—H7C109.5H18A—C18—H18B109.5
N1—C8—C9127.1 (2)C17—C18—H18C109.5
N1—C8—H8116.4H18A—C18—H18C109.5
C9—C8—H8116.4H18B—C18—H18C109.5
O3—S1—C1—C6159.2 (2)N1—C8—C9—C107.0 (4)
O2—S1—C1—C6−79.3 (2)C8—C9—C10—O62.7 (3)
O1—S1—C1—C639.4 (2)C14—C9—C10—O6−176.7 (2)
O3—S1—C1—C2−17.3 (3)C8—C9—C10—C11−177.9 (2)
O2—S1—C1—C2104.2 (2)C14—C9—C10—C112.7 (3)
O1—S1—C1—C2−137.1 (2)O6—C10—C11—C12178.9 (2)
C6—C1—C2—C3−2.6 (4)C9—C10—C11—C12−0.6 (4)
S1—C1—C2—C3173.88 (17)C15—N2—C12—C11−3.9 (4)
C1—C2—C3—C41.2 (3)C17—N2—C12—C11179.4 (2)
C1—C2—C3—C7−176.6 (2)C15—N2—C12—C13176.3 (2)
C2—C3—C4—C51.4 (3)C17—N2—C12—C13−0.4 (4)
C7—C3—C4—C5179.2 (2)C10—C11—C12—N2179.3 (2)
C2—C3—C4—N1−177.30 (19)C10—C11—C12—C13−1.0 (3)
C7—C3—C4—N10.5 (3)N2—C12—C13—C14179.9 (2)
C8—N1—C4—C5−12.5 (4)C11—C12—C13—C140.2 (4)
C8—N1—C4—C3166.3 (2)C12—C13—C14—C92.2 (4)
C3—C4—C5—C6−2.7 (4)C8—C9—C14—C13177.0 (2)
N1—C4—C5—C6176.0 (2)C10—C9—C14—C13−3.6 (4)
C4—C5—C6—C11.3 (4)C12—N2—C15—C16−78.0 (3)
C2—C1—C6—C51.3 (4)C17—N2—C15—C1698.9 (3)
S1—C1—C6—C5−175.2 (2)C12—N2—C17—C1885.9 (3)
C4—N1—C8—C9−179.1 (2)C15—N2—C17—C18−91.0 (3)
N1—C8—C9—C14−173.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O60.862.102.723 (3)129
N1—H1···O2i0.862.583.160 (3)125
O6—H6···O2ii0.821.912.709 (3)166
O4—H16···O3i0.852.002.828 (5)166
O5—H18···N1iii0.852.513.35 (3)174
C2—H2···O30.932.562.915 (4)103
C5—H5···O1iv0.932.553.392 (3)150
C7—H7B···O2i0.962.443.325 (3)154
C8—H8···O1iv0.932.433.353 (3)172
C15—H15B···O3ii0.972.503.444 (4)166
C16—H16C···O5v0.962.513.42 (3)160

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x+1/2, −y+1/2, z+1/2; (iii) x, y, z+1; (iv) −x+1/2, y+1/2, −z−1/2; (v) −x+1, y, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2871).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bu, X. H., Gao, Y. X., Chen, W. & Zhang, R. H. (2001). J. Rare Earth, 19, 70–75.
  • Ranford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem.37, 1226–1231. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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