PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1583.
Published online 2008 July 23. doi:  10.1107/S1600536808022691
PMCID: PMC2962200

N′-(2-Hydr­oxy-5-nitro­benzyl­idene)benzene­sulfonohydrazide

Abstract

The mol­ecule of the title compound, C13H11N3O5S, shows a phenyl group and an almost planar intra­molecularly hydrogen-bonded N′-(2-hydr­oxy-5-phenyl­ebenzyl­idene)hydrazino group disposed about the S atom. Adjacent mol­ecules are linked by N—H(...)Onitro hydrogen bonds, producing a linear chain that runs along the b axis of the unit cell.

Related literature

For 2′-[1-(2-hydroxy­phen­yl)ethyl­idene]benzene­sulfono­hydra­zide, see: Tai et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1583-scheme1.jpg

Experimental

Crystal data

  • C13H11N3O5S
  • M r = 321.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1583-efi1.jpg
  • a = 7.8188 (1) Å
  • b = 14.5904 (2) Å
  • c = 11.9083 (1) Å
  • β = 98.159 (1)°
  • V = 1344.74 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 100 (2) K
  • 0.47 × 0.40 × 0.33 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.883, T max = 0.916
  • 16761 measured reflections
  • 3089 independent reflections
  • 2972 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.088
  • S = 1.03
  • 3089 reflections
  • 243 parameters
  • 11 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.42 e Å−3
  • Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022691/im2077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022691/im2077Isup2.hkl

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

Acknowledgments

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The molecules of benzenesulfonic acid-(2-hydroxy-5-nitro-benzylidene)-hydrazide adopt a linear chain-like structure in which the individual molecules are linked by N–H···O hydrogen bonds [3.093 (3) Å] (Tai et al., 2008). The title compound exhibits a phenyl group and an almost planar, intramolecularly hydrogen-bonded (2-hydroxy-5-phenyl)ethylidenehydrazidyl group disposed about the sulfur atom. The nitro group is situated para with respect to the OH donor site (Scheme I, Fig. 1). The nitro group also acts as an acceptor towards the amino group of an adjacent molecule to furnish a chain-like structure that runs along the b-axis of the unit cell (Fig. 2).

Experimental

2-Hydroxy-5-nitrobenzaldehyde (0.50 g, 3 mmol) and benzene sulfonylhydrazide (0.52 g, 0.3 mmol) were condensed in refluxing ethanol (100 ml) for two hours. The solvent was removed to give the Schiff base, which was collected in nearly quantative yield. and dried. Crystals were obtained by recrystallization from ethanol.

Refinement

All hydrogen atoms were located in a difference Fouier map, and were refined with distance restraints of C–H 0.95±0.01, N–H 0.88±0.01 and O–H 0.84±0.01 Å. Their temperature factors were refined freely.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) plot of C13H11N3O5S at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Hydrogen-bonded chain structure. Hydrogen bonds are denoted by dashed lines.

Crystal data

C13H11N3O5SF000 = 664
Mr = 321.31Dx = 1.587 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9991 reflections
a = 7.8188 (1) Åθ = 2.4–30.4º
b = 14.5904 (2) ŵ = 0.27 mm1
c = 11.9083 (1) ÅT = 100 (2) K
β = 98.159 (1)ºTriangular plate, yellow
V = 1344.74 (3) Å30.47 × 0.40 × 0.33 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3089 independent reflections
Radiation source: fine-focus sealed tube2972 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 100(2) Kθmax = 27.5º
ω scansθmin = 2.2º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −10→9
Tmin = 0.883, Tmax = 0.916k = −18→18
16761 measured reflectionsl = −14→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0521P)2 + 0.7306P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3089 reflectionsΔρmax = 0.42 e Å3
243 parametersΔρmin = −0.51 e Å3
11 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
S10.78969 (4)0.172790 (19)0.37657 (2)0.01358 (10)
N10.89489 (14)0.67461 (7)0.75588 (9)0.0169 (2)
N20.82479 (13)0.33431 (7)0.46383 (9)0.0149 (2)
N30.89849 (13)0.24787 (7)0.46141 (9)0.0150 (2)
O10.65151 (13)0.47538 (6)0.36923 (8)0.0233 (2)
O20.84138 (13)0.75301 (6)0.76435 (8)0.0239 (2)
O31.00400 (12)0.63904 (7)0.82771 (8)0.0224 (2)
O40.74085 (13)0.21585 (7)0.26881 (7)0.0230 (2)
O50.89964 (11)0.09391 (6)0.38421 (8)0.01914 (19)
C10.70881 (16)0.52031 (8)0.46569 (10)0.0166 (2)
C20.66093 (17)0.61234 (9)0.47357 (11)0.0202 (3)
C30.71928 (16)0.66280 (8)0.56918 (11)0.0181 (2)
C40.82690 (15)0.62056 (8)0.65697 (10)0.0150 (2)
C50.87528 (15)0.52972 (8)0.65268 (10)0.0146 (2)
C60.81634 (15)0.47794 (8)0.55664 (10)0.0143 (2)
C70.87482 (15)0.38342 (8)0.55157 (10)0.0149 (2)
C80.60116 (14)0.14633 (8)0.43497 (10)0.0129 (2)
C90.58974 (16)0.16378 (8)0.54832 (10)0.0157 (2)
C100.44273 (17)0.13509 (9)0.59181 (11)0.0208 (3)
C110.31115 (16)0.08982 (9)0.52296 (13)0.0231 (3)
C120.32481 (16)0.07308 (9)0.41038 (13)0.0231 (3)
C130.47021 (16)0.10120 (9)0.36497 (11)0.0189 (2)
H1O0.692 (3)0.4223 (8)0.3795 (18)0.043 (6)*
H3N0.944 (2)0.2249 (12)0.5268 (10)0.027 (4)*
H20.587 (2)0.6401 (12)0.4127 (12)0.028 (4)*
H30.691 (2)0.7249 (7)0.5788 (15)0.025 (4)*
H50.9475 (18)0.5022 (10)0.7134 (11)0.019 (4)*
H70.9524 (18)0.3611 (11)0.6142 (10)0.019 (4)*
H90.6803 (17)0.1930 (11)0.5961 (12)0.023 (4)*
H100.431 (2)0.1463 (13)0.6687 (9)0.033 (5)*
H110.2133 (16)0.0685 (11)0.5530 (14)0.026 (4)*
H120.2367 (19)0.0410 (11)0.3635 (13)0.030 (4)*
H130.482 (2)0.0875 (11)0.2882 (9)0.025 (4)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.01629 (16)0.01318 (16)0.01162 (15)−0.00058 (9)0.00324 (11)−0.00033 (9)
N10.0174 (5)0.0180 (5)0.0160 (5)−0.0050 (4)0.0042 (4)−0.0018 (4)
N20.0170 (5)0.0106 (4)0.0175 (5)−0.0002 (3)0.0038 (4)0.0021 (3)
N30.0161 (5)0.0110 (4)0.0174 (5)−0.0007 (4)0.0006 (4)0.0002 (4)
O10.0356 (5)0.0154 (4)0.0158 (4)0.0037 (4)−0.0069 (4)−0.0016 (3)
O20.0272 (5)0.0183 (4)0.0260 (5)−0.0003 (4)0.0035 (4)−0.0078 (4)
O30.0245 (5)0.0236 (5)0.0174 (4)−0.0045 (4)−0.0028 (4)−0.0012 (3)
O40.0299 (5)0.0266 (5)0.0125 (4)−0.0012 (4)0.0028 (4)0.0040 (3)
O50.0187 (4)0.0158 (4)0.0240 (5)0.0009 (3)0.0067 (3)−0.0037 (3)
C10.0203 (6)0.0150 (6)0.0139 (5)−0.0006 (4)0.0003 (4)0.0002 (4)
C20.0250 (6)0.0160 (6)0.0180 (6)0.0030 (5)−0.0024 (5)0.0018 (4)
C30.0205 (6)0.0133 (5)0.0204 (6)0.0012 (4)0.0026 (5)0.0000 (4)
C40.0162 (5)0.0153 (5)0.0137 (5)−0.0037 (4)0.0031 (4)−0.0018 (4)
C50.0149 (5)0.0158 (5)0.0132 (5)−0.0022 (4)0.0020 (4)0.0023 (4)
C60.0156 (5)0.0132 (5)0.0142 (5)−0.0016 (4)0.0028 (4)0.0018 (4)
C70.0156 (5)0.0136 (5)0.0158 (5)−0.0012 (4)0.0027 (4)0.0034 (4)
C80.0132 (5)0.0109 (5)0.0148 (5)0.0008 (4)0.0023 (4)0.0007 (4)
C90.0162 (5)0.0163 (5)0.0147 (5)0.0007 (4)0.0020 (4)0.0001 (4)
C100.0210 (6)0.0215 (6)0.0214 (6)0.0038 (5)0.0084 (5)0.0036 (5)
C110.0156 (6)0.0169 (6)0.0383 (8)0.0020 (4)0.0090 (5)0.0046 (5)
C120.0154 (6)0.0164 (6)0.0359 (7)−0.0010 (4)−0.0020 (5)−0.0038 (5)
C130.0183 (6)0.0172 (6)0.0199 (6)0.0012 (4)−0.0020 (4)−0.0036 (4)

Geometric parameters (Å, °)

S1—O41.4312 (9)C3—H30.943 (9)
S1—O51.4316 (9)C4—C51.3812 (17)
S1—N31.6434 (10)C5—C61.3934 (16)
S1—C81.7597 (12)C5—H50.942 (9)
N1—O21.2271 (14)C6—C71.4569 (16)
N1—O31.2336 (14)C7—H70.950 (9)
N1—C41.4540 (15)C8—C91.3889 (16)
N2—C71.2815 (16)C8—C131.3908 (16)
N2—N31.3886 (13)C9—C101.3905 (17)
N3—H3N0.875 (9)C9—H90.945 (9)
O1—C11.3431 (14)C10—C111.3884 (19)
O1—H1O0.838 (9)C10—H100.947 (9)
C1—C21.4006 (17)C11—C121.382 (2)
C1—C61.4155 (16)C11—H110.942 (9)
C2—C31.3780 (17)C12—C131.3884 (19)
C2—H20.952 (9)C12—H120.947 (9)
C3—C41.3897 (17)C13—H130.953 (9)
O4—S1—O5119.43 (6)C4—C5—H5121.2 (10)
O4—S1—N3107.91 (6)C6—C5—H5119.4 (10)
O5—S1—N3104.06 (5)C5—C6—C1118.86 (11)
O4—S1—C8108.59 (6)C5—C6—C7118.56 (10)
O5—S1—C8109.12 (5)C1—C6—C7122.52 (11)
N3—S1—C8107.03 (5)N2—C7—C6120.12 (11)
O2—N1—O3123.06 (11)N2—C7—H7122.4 (10)
O2—N1—C4118.84 (10)C6—C7—H7117.4 (10)
O3—N1—C4118.09 (10)C9—C8—C13121.73 (11)
C7—N2—N3116.43 (10)C9—C8—S1121.12 (9)
N2—N3—S1115.98 (8)C13—C8—S1116.98 (9)
N2—N3—H3N116.5 (12)C8—C9—C10118.51 (11)
S1—N3—H3N113.7 (12)C8—C9—H9121.5 (10)
C1—O1—H1O104.7 (15)C10—C9—H9120.0 (10)
O1—C1—C2117.73 (10)C11—C10—C9120.38 (12)
O1—C1—C6122.07 (11)C11—C10—H10119.2 (12)
C2—C1—C6120.18 (11)C9—C10—H10120.4 (12)
C3—C2—C1120.48 (11)C12—C11—C10120.28 (12)
C3—C2—H2119.8 (11)C12—C11—H11119.3 (11)
C1—C2—H2119.7 (11)C10—C11—H11120.4 (11)
C2—C3—C4118.60 (11)C11—C12—C13120.40 (12)
C2—C3—H3123.8 (11)C11—C12—H12120.7 (11)
C4—C3—H3117.6 (11)C13—C12—H12118.9 (11)
C5—C4—C3122.51 (11)C12—C13—C8118.71 (12)
C5—C4—N1118.68 (10)C12—C13—H13120.5 (11)
C3—C4—N1118.79 (11)C8—C13—H13120.8 (11)
C4—C5—C6119.35 (11)
C7—N2—N3—S1158.80 (9)O1—C1—C6—C71.05 (19)
O4—S1—N3—N247.89 (10)C2—C1—C6—C7−177.91 (11)
O5—S1—N3—N2175.72 (8)N3—N2—C7—C6174.40 (10)
C8—S1—N3—N2−68.82 (9)C5—C6—C7—N2−179.10 (11)
O1—C1—C2—C3−178.31 (12)C1—C6—C7—N2−2.18 (18)
C6—C1—C2—C30.69 (19)O4—S1—C8—C9−135.67 (10)
C1—C2—C3—C40.3 (2)O5—S1—C8—C992.63 (10)
C2—C3—C4—C5−1.02 (19)N3—S1—C8—C9−19.41 (11)
C2—C3—C4—N1177.34 (11)O4—S1—C8—C1348.99 (11)
O2—N1—C4—C5−174.10 (11)O5—S1—C8—C13−82.72 (10)
O3—N1—C4—C55.76 (16)N3—S1—C8—C13165.25 (9)
O2—N1—C4—C37.48 (17)C13—C8—C9—C10−0.06 (18)
O3—N1—C4—C3−172.65 (11)S1—C8—C9—C10−175.19 (9)
C3—C4—C5—C60.71 (18)C8—C9—C10—C110.18 (18)
N1—C4—C5—C6−177.64 (10)C9—C10—C11—C12−0.20 (19)
C4—C5—C6—C10.30 (17)C10—C11—C12—C130.1 (2)
C4—C5—C6—C7177.34 (10)C11—C12—C13—C80.03 (19)
O1—C1—C6—C5177.97 (11)C9—C8—C13—C12−0.04 (18)
C2—C1—C6—C5−0.99 (18)S1—C8—C13—C12175.28 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···N20.84 (1)1.86 (1)2.628 (1)153 (2)
N3—H3n···O3i0.88 (1)2.13 (1)2.978 (1)163 (2)

Symmetry codes: (i) −x+2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2077).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tai, X.-S., Xu, J., Feng, Y.-M. & Liang, Z.-P. (2008). Acta Cryst. E64, o904. [PMC free article] [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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