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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2361.
Published online 2010 August 21. doi:  10.1107/S160053681003271X
PMCID: PMC3007915

(E)-N′-(9-Anthryl­methyl­idene)-p-toluene­sulfono­hydrazide

Abstract

The S—N(H)—N=C linkage in the title mol­ecule, C22H18N2O2S, is non-planar [torsion angle = 30.6 (1)°] as the amino N atom is pyramidally coordinated. In the crystal, the amino group acts as a hydrogen-bond donor to an O atom of an adjacent mol­ecule, generating chains running parallel to the b axis.

Related literature

For the structure of the (E)-N′-benzyl­idene-p-toluene­sulf­ono­hydrazide analog, see: Mehrabi et al. (2008 [triangle]).

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Object name is e-66-o2361-scheme1.jpg

Experimental

Crystal data

  • C22H18N2O2S
  • M r = 374.44
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2361-efi1.jpg
  • a = 17.3634 (15) Å
  • b = 9.2438 (8) Å
  • c = 22.882 (2) Å
  • V = 3672.6 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 100 K
  • 0.40 × 0.20 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.926, T max = 0.990
  • 22220 measured reflections
  • 4209 independent reflections
  • 3158 reflections with I > 2σ(I)
  • R int = 0.055

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.104
  • S = 1.02
  • 4209 reflections
  • 249 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003271X/pk2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003271X/pk2262Isup2.hkl

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

p-Toluenesulfonyl hydrazide, CH3-4-C6H4SO2NHNH2, condenses with carbonyl compounds to form Schiff bases, and among the plethora, nearly a hundred have had their crystal structures determined. The compounds have the azomethine double-bond in an E-configuration. In the Schiff base product between p-toluenesulfonyl hydrazide and thiophene-2-carboxaldehyde, the S–N(H)–N═C linkage is non-planar [torsion angle 30.6 (1) °] as the amino nitrogen atom (which bears a hydrogen atom) is pyramidally coordinated (Fig. 1). The amino group acts as a hydrogen-bond donor to an oxygen atom of an adjacent molecule to generate chains running parallel to the b-axis of the cell (Fig. 2).

Experimental

p-Toluenesulfonyl hydrazide (4.66 g, 2.5 mmol) and anthracene-9-carboxaldehyde (5.162.80 g, 2.5 mmol) were heated in methanol (50 ml) for two hours. The cool solution yielded a precipitate that was recrystallized from ethanol and collected in 90% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C–H 0.95 to 0.99 Å, U(H) 1.2 to 1.5Ueq(C)] and were included in the refinement in the riding model approximation. The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint [N–H 0.86 (1) Å]; its temperature factor was freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C22H18N2O2S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
A view of the chain structure resulting from N—H···O hydrogen-bonding.

Crystal data

C22H18N2O2SF(000) = 1568
Mr = 374.44Dx = 1.354 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3593 reflections
a = 17.3634 (15) Åθ = 2.3–27.6°
b = 9.2438 (8) ŵ = 0.20 mm1
c = 22.882 (2) ÅT = 100 K
V = 3672.6 (6) Å3Prism, yellow
Z = 80.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer4209 independent reflections
Radiation source: fine-focus sealed tube3158 reflections with I > 2σ(I)
graphiteRint = 0.055
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→22
Tmin = 0.926, Tmax = 0.990k = −12→10
22220 measured reflectionsl = −29→29

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0442P)2 + 1.8913P] where P = (Fo2 + 2Fc2)/3
4209 reflections(Δ/σ)max = 0.001
249 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = −0.46 e Å3

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

xyzUiso*/Ueq
S10.70021 (2)0.57688 (5)0.781940 (19)0.01816 (12)
O10.67930 (7)0.71367 (13)0.75666 (6)0.0228 (3)
O20.75969 (7)0.57170 (14)0.82533 (5)0.0244 (3)
N10.73235 (8)0.47229 (17)0.72874 (6)0.0188 (3)
H10.7581 (11)0.4002 (17)0.7419 (9)0.032 (6)*
N20.67630 (8)0.44447 (16)0.68590 (6)0.0187 (3)
C10.61574 (10)0.4956 (2)0.80808 (8)0.0207 (4)
C20.54464 (11)0.5595 (2)0.79729 (9)0.0263 (4)
H20.54120.64740.77600.032*
C30.47881 (11)0.4919 (2)0.81839 (9)0.0324 (5)
H30.42990.53410.81110.039*
C40.48310 (12)0.3638 (2)0.84988 (9)0.0319 (5)
C50.55497 (13)0.3014 (2)0.85908 (9)0.0326 (5)
H50.55840.21290.88000.039*
C60.62165 (11)0.3659 (2)0.83825 (8)0.0256 (4)
H60.67050.32200.84450.031*
C70.41088 (13)0.2933 (3)0.87297 (10)0.0437 (6)
H7A0.37550.36790.88720.066*
H7B0.42420.22790.90510.066*
H7C0.38610.23820.84160.066*
C80.68260 (10)0.32154 (19)0.66045 (7)0.0190 (4)
H80.72240.25800.67270.023*
C90.63107 (10)0.27431 (19)0.61321 (7)0.0181 (4)
C100.55246 (10)0.31693 (19)0.61075 (8)0.0196 (4)
C110.51458 (10)0.3970 (2)0.65569 (8)0.0225 (4)
H110.54340.42920.68850.027*
C120.43788 (11)0.4284 (2)0.65260 (9)0.0256 (4)
H120.41390.47890.68390.031*
C130.39353 (11)0.3870 (2)0.60350 (9)0.0284 (4)
H130.34060.41240.60130.034*
C140.42673 (11)0.3113 (2)0.55987 (9)0.0274 (4)
H140.39680.28490.52680.033*
C150.50621 (10)0.2698 (2)0.56239 (8)0.0232 (4)
C160.53801 (11)0.1800 (2)0.51995 (8)0.0248 (4)
H160.50710.15110.48770.030*
C170.61374 (10)0.1311 (2)0.52330 (8)0.0207 (4)
C180.64417 (11)0.0329 (2)0.48093 (8)0.0249 (4)
H180.61210.00050.45000.030*
C190.71804 (11)−0.0149 (2)0.48399 (8)0.0247 (4)
H190.7372−0.08080.45570.030*
C200.76612 (11)0.0344 (2)0.52973 (8)0.0229 (4)
H200.81790.00170.53160.028*
C210.73965 (10)0.1276 (2)0.57109 (8)0.0204 (4)
H210.77360.15940.60100.025*
C220.66168 (10)0.17906 (19)0.57053 (7)0.0184 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0166 (2)0.0169 (2)0.0210 (2)−0.00194 (17)0.00059 (17)−0.00158 (17)
O10.0222 (7)0.0163 (6)0.0300 (7)−0.0008 (5)0.0016 (5)0.0003 (5)
O20.0203 (7)0.0287 (7)0.0241 (7)−0.0025 (6)−0.0044 (5)−0.0040 (6)
N10.0164 (7)0.0189 (8)0.0211 (8)0.0014 (6)−0.0012 (6)−0.0008 (6)
N20.0167 (7)0.0209 (8)0.0184 (7)−0.0022 (6)−0.0009 (6)−0.0003 (6)
C10.0204 (9)0.0205 (9)0.0212 (9)−0.0052 (7)0.0050 (7)−0.0043 (7)
C20.0219 (9)0.0249 (10)0.0323 (10)−0.0008 (8)0.0037 (8)−0.0067 (8)
C30.0222 (10)0.0366 (12)0.0386 (12)−0.0036 (9)0.0077 (9)−0.0149 (10)
C40.0330 (11)0.0353 (12)0.0274 (10)−0.0164 (9)0.0122 (9)−0.0173 (9)
C50.0449 (13)0.0250 (11)0.0279 (10)−0.0115 (9)0.0087 (9)−0.0030 (9)
C60.0296 (10)0.0220 (10)0.0252 (9)−0.0029 (8)0.0049 (8)−0.0017 (8)
C70.0381 (13)0.0554 (16)0.0375 (12)−0.0261 (11)0.0144 (10)−0.0162 (11)
C80.0177 (9)0.0198 (9)0.0195 (9)0.0003 (7)0.0016 (7)0.0035 (7)
C90.0190 (9)0.0171 (9)0.0182 (8)−0.0017 (7)0.0004 (7)0.0026 (7)
C100.0187 (9)0.0184 (9)0.0216 (9)−0.0010 (7)−0.0008 (7)0.0031 (7)
C110.0197 (9)0.0241 (10)0.0238 (9)−0.0020 (7)0.0005 (7)−0.0015 (8)
C120.0220 (9)0.0249 (10)0.0300 (10)0.0017 (8)0.0035 (8)−0.0020 (8)
C130.0184 (9)0.0299 (11)0.0369 (11)0.0042 (8)−0.0030 (8)0.0015 (9)
C140.0229 (10)0.0311 (11)0.0282 (10)0.0044 (8)−0.0083 (8)−0.0004 (9)
C150.0213 (9)0.0248 (10)0.0235 (9)0.0015 (8)−0.0036 (7)0.0035 (8)
C160.0243 (10)0.0297 (10)0.0203 (9)0.0018 (8)−0.0067 (8)−0.0007 (8)
C170.0222 (9)0.0218 (9)0.0182 (8)0.0009 (7)−0.0005 (7)0.0022 (7)
C180.0274 (10)0.0283 (10)0.0191 (9)−0.0004 (8)−0.0040 (8)−0.0010 (8)
C190.0289 (10)0.0252 (10)0.0200 (9)0.0015 (8)0.0039 (8)−0.0007 (8)
C200.0199 (9)0.0231 (10)0.0258 (10)0.0020 (7)0.0023 (7)0.0031 (8)
C210.0193 (9)0.0210 (9)0.0210 (8)−0.0010 (7)0.0005 (7)0.0019 (7)
C220.0199 (9)0.0176 (9)0.0176 (8)−0.0018 (7)0.0001 (7)0.0046 (7)

Geometric parameters (Å, °)

S1—O11.4370 (13)C9—C101.422 (2)
S1—O21.4334 (13)C10—C111.428 (2)
S1—N11.6516 (15)C10—C151.435 (2)
S1—C11.7532 (18)C11—C121.365 (3)
N1—N21.405 (2)C11—H110.9500
N1—H10.857 (9)C12—C131.415 (3)
N2—C81.281 (2)C12—H120.9500
C1—C61.387 (3)C13—C141.349 (3)
C1—C21.391 (3)C13—H130.9500
C2—C31.389 (3)C14—C151.434 (3)
C2—H20.9500C14—H140.9500
C3—C41.388 (3)C15—C161.392 (3)
C3—H30.9500C16—C171.392 (3)
C4—C51.391 (3)C16—H160.9500
C4—C71.509 (3)C17—C181.429 (3)
C5—C61.387 (3)C17—C221.434 (2)
C5—H50.9500C18—C191.358 (3)
C6—H60.9500C18—H180.9500
C7—H7A0.9800C19—C201.414 (3)
C7—H7B0.9800C19—H190.9500
C7—H7C0.9800C20—C211.360 (2)
C8—C91.470 (2)C20—H200.9500
C8—H80.9500C21—C221.435 (2)
C9—C221.418 (2)C21—H210.9500
O1—S1—O2119.35 (8)C9—C10—C11123.88 (16)
O1—S1—N1107.68 (8)C9—C10—C15118.93 (16)
O2—S1—N1104.33 (8)C11—C10—C15117.07 (16)
O1—S1—C1107.65 (8)C12—C11—C10121.50 (18)
O2—S1—C1110.62 (8)C12—C11—H11119.3
N1—S1—C1106.45 (8)C10—C11—H11119.3
N2—N1—S1112.79 (11)C11—C12—C13120.98 (18)
N2—N1—H1117.7 (15)C11—C12—H12119.5
S1—N1—H1111.8 (14)C13—C12—H12119.5
C8—N2—N1114.84 (15)C14—C13—C12119.71 (17)
C6—C1—C2121.41 (17)C14—C13—H13120.1
C6—C1—S1118.58 (14)C12—C13—H13120.1
C2—C1—S1120.00 (15)C13—C14—C15121.36 (18)
C3—C2—C1118.52 (19)C13—C14—H14119.3
C3—C2—H2120.7C15—C14—H14119.3
C1—C2—H2120.7C16—C15—C10119.80 (16)
C4—C3—C2121.3 (2)C16—C15—C14120.89 (17)
C4—C3—H3119.3C10—C15—C14119.26 (17)
C2—C3—H3119.3C17—C16—C15122.00 (17)
C3—C4—C5118.72 (18)C17—C16—H16119.0
C3—C4—C7120.4 (2)C15—C16—H16119.0
C5—C4—C7120.9 (2)C16—C17—C18121.19 (17)
C6—C5—C4121.3 (2)C16—C17—C22119.28 (17)
C6—C5—H5119.4C18—C17—C22119.52 (16)
C4—C5—H5119.4C19—C18—C17121.39 (17)
C5—C6—C1118.73 (19)C19—C18—H18119.3
C5—C6—H6120.6C17—C18—H18119.3
C1—C6—H6120.6C18—C19—C20119.38 (17)
C4—C7—H7A109.5C18—C19—H19120.3
C4—C7—H7B109.5C20—C19—H19120.3
H7A—C7—H7B109.5C21—C20—C19121.31 (17)
C4—C7—H7C109.5C21—C20—H20119.3
H7A—C7—H7C109.5C19—C20—H20119.3
H7B—C7—H7C109.5C20—C21—C22121.52 (17)
N2—C8—C9123.06 (16)C20—C21—H21119.2
N2—C8—H8118.5C22—C21—H21119.2
C9—C8—H8118.5C9—C22—C21123.60 (16)
C22—C9—C10120.31 (16)C9—C22—C17119.55 (16)
C22—C9—C8117.56 (15)C21—C22—C17116.85 (16)
C10—C9—C8122.09 (16)
O1—S1—N1—N2−62.00 (13)C10—C11—C12—C13−2.3 (3)
O2—S1—N1—N2170.23 (11)C11—C12—C13—C142.1 (3)
C1—S1—N1—N253.21 (14)C12—C13—C14—C150.9 (3)
S1—N1—N2—C8−149.39 (13)C9—C10—C15—C162.1 (3)
O1—S1—C1—C6−175.60 (14)C11—C10—C15—C16−174.03 (17)
O2—S1—C1—C6−43.59 (17)C9—C10—C15—C14179.46 (17)
N1—S1—C1—C669.17 (16)C11—C10—C15—C143.4 (3)
O1—S1—C1—C25.81 (18)C13—C14—C15—C16173.73 (19)
O2—S1—C1—C2137.82 (15)C13—C14—C15—C10−3.6 (3)
N1—S1—C1—C2−109.42 (16)C10—C15—C16—C171.3 (3)
C6—C1—C2—C31.2 (3)C14—C15—C16—C17−176.08 (18)
S1—C1—C2—C3179.71 (15)C15—C16—C17—C18176.73 (18)
C1—C2—C3—C40.3 (3)C15—C16—C17—C22−2.6 (3)
C2—C3—C4—C5−1.4 (3)C16—C17—C18—C19179.93 (18)
C2—C3—C4—C7179.28 (18)C22—C17—C18—C19−0.8 (3)
C3—C4—C5—C61.0 (3)C17—C18—C19—C20−0.6 (3)
C7—C4—C5—C6−179.68 (18)C18—C19—C20—C210.7 (3)
C4—C5—C6—C10.4 (3)C19—C20—C21—C220.6 (3)
C2—C1—C6—C5−1.6 (3)C10—C9—C22—C21−177.99 (16)
S1—C1—C6—C5179.88 (14)C8—C9—C22—C21−0.2 (3)
N1—N2—C8—C9−178.04 (15)C10—C9—C22—C172.8 (3)
N2—C8—C9—C22149.92 (17)C8—C9—C22—C17−179.43 (15)
N2—C8—C9—C10−32.4 (3)C20—C21—C22—C9178.91 (17)
C22—C9—C10—C11171.73 (17)C20—C21—C22—C17−1.9 (3)
C8—C9—C10—C11−5.9 (3)C16—C17—C22—C90.5 (3)
C22—C9—C10—C15−4.1 (3)C18—C17—C22—C9−178.81 (17)
C8—C9—C10—C15178.27 (16)C16—C17—C22—C21−178.75 (17)
C9—C10—C11—C12−176.38 (18)C18—C17—C22—C211.9 (2)
C15—C10—C11—C12−0.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.86 (1)2.07 (1)2.911 (2)169 (2)

Symmetry codes: (i) −x+3/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2262).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mehrabi, H., Kia, R., Hassanzadeh, A., Ghobadi, S. & Khavasi, H. R. (2008). Acta Cryst. E64, o1845. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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