organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 10 July 2008; accepted 19 July 2008; online 23 July 2008)

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[Tai, X.-S., Xu, J., Feng, Y.-M. & Liang, Z.-P. (2008). Acta Cryst. E64, o904.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11N3O5S

  • Mr = 321.31

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.883, Tmax = 0.916

  • 16761 measured reflections

  • 3089 independent reflections

  • 2972 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯N2 0.84 (1) 1.86 (1) 2.628 (1) 153 (2)
N3—H3n⋯O3i 0.88 (1) 2.13 (1) 2.978 (1) 163 (2)
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C13H11N3O5S at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Hydrogen-bonded chain structure. Hydrogen bonds are denoted by dashed lines.
N'-(2-Hydroxy-5-nitrobenzylidene)benzenesulfonohydrazide top
Crystal data top
C13H11N3O5SF(000) = 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 = 2.4–30.4°
b = 14.5904 (2) ŵ = 0.27 mm1
c = 11.9083 (1) ÅT = 100 K
β = 98.159 (1)°Triangular plate, yellow
V = 1344.74 (3) Å30.47 × 0.40 × 0.33 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
3089 independent reflections
Radiation source: fine-focus sealed tube2972 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 109
Tmin = 0.883, Tmax = 0.916k = 1818
16761 measured reflectionsl = 1415
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.7306P]
where P = (Fo2 + 2Fc2)/3
3089 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.42 e Å3
11 restraintsΔρmin = 0.51 e Å3
Crystal data top
C13H11N3O5SV = 1344.74 (3) Å3
Mr = 321.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8188 (1) ŵ = 0.27 mm1
b = 14.5904 (2) ÅT = 100 K
c = 11.9083 (1) Å0.47 × 0.40 × 0.33 mm
β = 98.159 (1)°
Data collection top
Bruker SMART APEX
diffractometer
3089 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2972 reflections with I > 2σ(I)
Tmin = 0.883, Tmax = 0.916Rint = 0.024
16761 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03211 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.42 e Å3
3089 reflectionsΔρmin = 0.51 e Å3
243 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C7177.91 (11)
O5—S1—N3—N2175.72 (8)N3—N2—C7—C6174.40 (10)
C8—S1—N3—N268.82 (9)C5—C6—C7—N2179.10 (11)
O1—C1—C2—C3178.31 (12)C1—C6—C7—N22.18 (18)
C6—C1—C2—C30.69 (19)O4—S1—C8—C9135.67 (10)
C1—C2—C3—C40.3 (2)O5—S1—C8—C992.63 (10)
C2—C3—C4—C51.02 (19)N3—S1—C8—C919.41 (11)
C2—C3—C4—N1177.34 (11)O4—S1—C8—C1348.99 (11)
O2—N1—C4—C5174.10 (11)O5—S1—C8—C1382.72 (10)
O3—N1—C4—C55.76 (16)N3—S1—C8—C13165.25 (9)
O2—N1—C4—C37.48 (17)C13—C8—C9—C100.06 (18)
O3—N1—C4—C3172.65 (11)S1—C8—C9—C10175.19 (9)
C3—C4—C5—C60.71 (18)C8—C9—C10—C110.18 (18)
N1—C4—C5—C6177.64 (10)C9—C10—C11—C120.20 (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—C120.04 (18)
C2—C1—C6—C50.99 (18)S1—C8—C13—C12175.28 (9)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x+2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H11N3O5S
Mr321.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)7.8188 (1), 14.5904 (2), 11.9083 (1)
β (°) 98.159 (1)
V3)1344.74 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.47 × 0.40 × 0.33
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.883, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
16761, 3089, 2972
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.088, 1.04
No. of reflections3089
No. of parameters243
No. of restraints11
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.42, 0.51

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
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 code: (i) x+2, y1/2, z+3/2.
 

Acknowledgements

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.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTai, X.-S., Xu, J., Feng, Y.-M. & Liang, Z.-P. (2008). Acta Cryst. E64, o904.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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