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

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ISSN: 2056-9890

N′-(2,5-Di­hydroxy­benzyl­­idene)benzene­sulfonohydrazide

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

(Received 7 January 2008; accepted 21 January 2008; online 25 January 2008)

In the title compound, C13H12N2O4S, the dihedral angle between the two aromatic rings is 89.5 (1)°. In the crystal structure, mol­ecules are linked by O—H⋯Ohydr­oxy and N—H⋯Osulfon­yl hydrogen bonds, forming a ribbon that propagates along the b axis; there is also an intra­molecular O—H⋯N hydrogen bond.

Related literature

For the structure of 2′-(5-bromo-2-hydroxy­benzyl­idene)­benzene­sulfonohydrazide, see: Ali et al. (2007[Ali, M. H., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1821-o1822.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12N2O4S

  • Mr = 292.31

  • Monoclinic, P 21 /n

  • a = 12.5814 (2) Å

  • b = 7.1601 (1) Å

  • c = 14.6727 (2) Å

  • β = 105.540 (1)°

  • V = 1273.46 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 128 (2) K

  • 0.65 × 0.33 × 0.29 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: none

  • 16406 measured reflections

  • 2924 independent reflections

  • 2684 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.104

  • S = 1.07

  • 2924 reflections

  • 229 parameters

  • 11 restraints

  • All H-atom parameters refined

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3O⋯N2 0.85 (1) 1.82 (2) 2.562 (2) 145 (2)
O4—H4O⋯O3i 0.85 (1) 1.85 (1) 2.698 (2) 175 (2)
N1—H1N⋯O1ii 0.85 (1) 2.05 (1) 2.897 (2) 171 (2)
Symmetry codes: (i) x, y-1, z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). 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

A recent study reported the crystal structure of 2'-(5-bromo-2-hydroxybenzylidene)benzenesulfonohydrazide (Ali et al., 2007). A second hydroxy group is introduced in the title compound.

Related literature top

For the structure of 2'-(5-bromo-2-hydroxybenzylidene)benzenesulfonohydrazide, see: Ali et al. (2007).

Experimental top

Benzenesulfohydrazine (0.29 g, 1.7 mmol) and 2,5-dihydroxybenzaldehyde (0.24 g, 1.7 mmol) were refluxed in ethanol (50 ml) for 2 h. The solvent was removed to give the product Schiff base, and crystals were obtained upon recrystallization from ethanol.

Refinement top

All hydrogen atoms were located in difference Fourier maps. Those bonded to C were restrained to 0.95±0.01 Å, and those bonded to N or O to 0.85±0.01 Å. All displacement parameters were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the ribbon structure of the title compound. Dashed lines indicate hydrogen bonds.
N'-(2,5-Dihydroxybenzylidene)benzenesulfonohydrazide top
Crystal data top
C13H12N2O4SF(000) = 608
Mr = 292.31Dx = 1.525 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9918 reflections
a = 12.5814 (2) Åθ = 5.0–63.2°
b = 7.1601 (1) ŵ = 0.27 mm1
c = 14.6727 (2) ÅT = 128 K
β = 105.540 (1)°Block, yellow
V = 1273.46 (3) Å30.65 × 0.33 × 0.29 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
2684 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 1.9°
ϕ and ω scansh = 1616
16406 measured reflectionsk = 99
2924 independent reflectionsl = 1819
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0666P)2 + 0.482P]
where P = (Fo2 + 2Fc2)/3
2924 reflections(Δ/σ)max = 0.001
229 parametersΔρmax = 0.40 e Å3
11 restraintsΔρmin = 0.35 e Å3
Crystal data top
C13H12N2O4SV = 1273.46 (3) Å3
Mr = 292.31Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.5814 (2) ŵ = 0.27 mm1
b = 7.1601 (1) ÅT = 128 K
c = 14.6727 (2) Å0.65 × 0.33 × 0.29 mm
β = 105.540 (1)°
Data collection top
Bruker APEXII
diffractometer
2684 reflections with I > 2σ(I)
16406 measured reflectionsRint = 0.023
2924 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03111 restraints
wR(F2) = 0.104All H-atom parameters refined
S = 1.07Δρmax = 0.40 e Å3
2924 reflectionsΔρmin = 0.35 e Å3
229 parameters
Special details top

Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.77742 (3)0.75958 (4)0.66733 (2)0.01720 (12)
N10.83576 (9)0.55528 (16)0.65868 (8)0.0190 (2)
N20.84430 (9)0.52079 (16)0.56754 (8)0.0186 (2)
O10.77923 (9)0.76844 (15)0.76588 (7)0.0245 (2)
O20.83351 (8)0.89724 (14)0.62689 (7)0.0249 (2)
O30.85080 (9)0.64124 (14)0.40471 (7)0.0276 (2)
O40.91487 (10)0.08605 (15)0.30407 (8)0.0307 (3)
C10.63909 (11)0.74943 (17)0.59938 (9)0.0164 (3)
C20.61433 (11)0.7976 (2)0.50377 (9)0.0198 (3)
C30.50524 (12)0.7887 (2)0.44977 (10)0.0228 (3)
C40.42314 (12)0.7347 (2)0.49182 (11)0.0241 (3)
C50.44840 (12)0.6872 (2)0.58702 (11)0.0242 (3)
C60.55757 (11)0.69292 (19)0.64210 (9)0.0204 (3)
C70.86202 (10)0.35212 (19)0.54498 (9)0.0182 (3)
C80.87129 (10)0.31449 (19)0.44957 (9)0.0175 (3)
C90.88699 (11)0.12938 (19)0.42327 (10)0.0199 (3)
C100.89662 (11)0.08955 (19)0.33332 (10)0.0220 (3)
C110.88899 (13)0.2343 (2)0.26805 (10)0.0248 (3)
C120.87375 (12)0.4168 (2)0.29252 (10)0.0248 (3)
C130.86505 (11)0.45797 (19)0.38301 (9)0.0203 (3)
H3O0.8478 (19)0.650 (3)0.4615 (8)0.052 (6)*
H4O0.8920 (18)0.168 (3)0.3363 (15)0.050 (6)*
H1N0.8083 (15)0.470 (2)0.6862 (13)0.034 (5)*
H20.6718 (11)0.834 (2)0.4758 (12)0.026 (4)*
H30.4885 (15)0.824 (3)0.3850 (7)0.031 (5)*
H40.3471 (18)0.729 (3)0.4543 (14)0.033 (5)*
H50.3922 (12)0.651 (3)0.6166 (12)0.032 (5)*
H60.5728 (13)0.657 (2)0.7068 (7)0.024 (4)*
H70.8721 (15)0.2494 (17)0.5872 (10)0.019 (4)*
H90.8924 (15)0.031 (2)0.4681 (10)0.028 (4)*
H110.8879 (18)0.201 (3)0.2057 (8)0.045 (6)*
H120.8656 (15)0.515 (2)0.2476 (11)0.032 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01696 (19)0.01935 (18)0.01461 (19)0.00098 (10)0.00306 (13)0.00294 (10)
N10.0212 (5)0.0213 (5)0.0157 (5)0.0023 (4)0.0070 (4)0.0008 (4)
N20.0174 (5)0.0235 (6)0.0161 (5)0.0000 (4)0.0066 (4)0.0005 (4)
O10.0261 (5)0.0312 (6)0.0144 (5)0.0025 (4)0.0025 (4)0.0053 (4)
O20.0229 (5)0.0226 (5)0.0288 (5)0.0048 (4)0.0065 (4)0.0010 (4)
O30.0434 (6)0.0195 (5)0.0232 (5)0.0037 (4)0.0147 (5)0.0033 (4)
O40.0461 (7)0.0225 (5)0.0318 (6)0.0037 (4)0.0249 (5)0.0047 (4)
C10.0166 (6)0.0173 (6)0.0150 (6)0.0003 (4)0.0037 (5)0.0022 (4)
C20.0210 (6)0.0231 (6)0.0164 (6)0.0009 (5)0.0069 (5)0.0010 (5)
C30.0235 (7)0.0274 (7)0.0163 (6)0.0028 (5)0.0033 (5)0.0013 (5)
C40.0187 (7)0.0266 (7)0.0247 (7)0.0007 (5)0.0020 (6)0.0034 (5)
C50.0208 (6)0.0255 (7)0.0281 (7)0.0030 (5)0.0097 (5)0.0006 (6)
C60.0225 (6)0.0219 (6)0.0176 (6)0.0010 (5)0.0069 (5)0.0010 (5)
C70.0162 (6)0.0214 (6)0.0175 (6)0.0003 (5)0.0054 (5)0.0018 (5)
C80.0148 (6)0.0219 (6)0.0167 (6)0.0003 (5)0.0058 (4)0.0011 (5)
C90.0200 (6)0.0207 (6)0.0211 (6)0.0002 (5)0.0091 (5)0.0018 (5)
C100.0220 (6)0.0220 (6)0.0253 (7)0.0025 (5)0.0118 (5)0.0027 (5)
C110.0286 (7)0.0300 (7)0.0187 (7)0.0033 (5)0.0116 (6)0.0017 (5)
C120.0298 (7)0.0260 (7)0.0201 (7)0.0009 (6)0.0095 (5)0.0051 (5)
C130.0202 (6)0.0200 (6)0.0214 (7)0.0011 (5)0.0071 (5)0.0010 (5)
Geometric parameters (Å, º) top
S1—O21.4304 (10)C4—C51.389 (2)
S1—O11.4415 (10)C4—H40.97 (2)
S1—N11.6567 (12)C5—C61.395 (2)
S1—C11.7602 (13)C5—H50.959 (9)
N1—N21.3920 (15)C6—H60.953 (9)
N1—H1N0.85 (1)C7—C81.4607 (17)
N2—C71.2874 (17)C7—H70.948 (9)
O3—C131.3733 (16)C8—C131.4051 (18)
O3—H3O0.85 (1)C8—C91.4090 (18)
O4—C101.3677 (16)C9—C101.3870 (19)
O4—H4O0.85 (1)C9—H90.953 (9)
C1—C21.3963 (18)C10—C111.397 (2)
C1—C61.3976 (18)C11—C121.382 (2)
C2—C31.3904 (19)C11—H110.943 (9)
C2—H20.958 (9)C12—C131.3928 (19)
C3—C41.392 (2)C12—H120.950 (9)
C3—H30.951 (9)
O2—S1—O1120.59 (6)C6—C5—H5118.4 (11)
O2—S1—N1107.38 (6)C5—C6—C1118.40 (12)
O1—S1—N1103.14 (6)C5—C6—H6118.2 (10)
O2—S1—C1108.44 (6)C1—C6—H6123.4 (10)
O1—S1—C1108.51 (6)N2—C7—C8118.90 (12)
N1—S1—C1108.14 (6)N2—C7—H7124.2 (10)
N2—N1—S1112.33 (9)C8—C7—H7116.9 (10)
N2—N1—H1N118.3 (13)C13—C8—C9118.90 (12)
S1—N1—H1N110.4 (13)C13—C8—C7121.83 (12)
C7—N2—N1118.47 (11)C9—C8—C7119.28 (12)
C13—O3—H3O110.2 (17)C10—C9—C8120.55 (12)
C10—O4—H4O110.5 (16)C10—C9—H9119.8 (11)
C2—C1—C6121.94 (12)C8—C9—H9119.6 (11)
C2—C1—S1118.65 (10)O4—C10—C9123.53 (13)
C6—C1—S1119.40 (10)O4—C10—C11116.96 (12)
C3—C2—C1118.80 (12)C9—C10—C11119.50 (13)
C3—C2—H2120.7 (11)C12—C11—C10120.81 (13)
C1—C2—H2120.5 (11)C12—C11—H11121.8 (14)
C2—C3—C4119.77 (13)C10—C11—H11117.1 (14)
C2—C3—H3118.6 (11)C11—C12—C13119.98 (13)
C4—C3—H3121.6 (11)C11—C12—H12121.0 (12)
C5—C4—C3121.10 (13)C13—C12—H12118.9 (12)
C5—C4—H4119.2 (12)O3—C13—C12118.16 (12)
C3—C4—H4119.7 (12)O3—C13—C8121.59 (12)
C4—C5—C6119.98 (13)C12—C13—C8120.25 (12)
C4—C5—H5121.6 (11)
O2—S1—N1—N250.34 (10)S1—C1—C6—C5179.56 (10)
O1—S1—N1—N2178.71 (8)N1—N2—C7—C8179.90 (10)
C1—S1—N1—N266.48 (10)N2—C7—C8—C132.14 (19)
S1—N1—N2—C7163.01 (10)N2—C7—C8—C9177.89 (12)
O2—S1—C1—C227.78 (12)C13—C8—C9—C100.28 (19)
O1—S1—C1—C2160.41 (10)C7—C8—C9—C10179.68 (12)
N1—S1—C1—C288.36 (11)C8—C9—C10—O4178.20 (12)
O2—S1—C1—C6152.52 (10)C8—C9—C10—C111.0 (2)
O1—S1—C1—C619.89 (12)O4—C10—C11—C12178.16 (14)
N1—S1—C1—C691.34 (11)C9—C10—C11—C121.0 (2)
C6—C1—C2—C30.1 (2)C10—C11—C12—C130.5 (2)
S1—C1—C2—C3179.64 (10)C11—C12—C13—O3179.51 (13)
C1—C2—C3—C40.8 (2)C11—C12—C13—C80.2 (2)
C2—C3—C4—C50.7 (2)C9—C8—C13—O3179.42 (12)
C3—C4—C5—C60.1 (2)C7—C8—C13—O30.5 (2)
C4—C5—C6—C10.8 (2)C9—C8—C13—C120.32 (19)
C2—C1—C6—C50.8 (2)C7—C8—C13—C12179.71 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···N20.85 (1)1.82 (2)2.562 (2)145 (2)
O4—H4O···O3i0.85 (1)1.85 (1)2.698 (2)175 (2)
N1—H1N···O1ii0.85 (1)2.05 (1)2.897 (2)171 (2)
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H12N2O4S
Mr292.31
Crystal system, space groupMonoclinic, P21/n
Temperature (K)128
a, b, c (Å)12.5814 (2), 7.1601 (1), 14.6727 (2)
β (°) 105.540 (1)
V3)1273.46 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.65 × 0.33 × 0.29
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16406, 2924, 2684
Rint0.023
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.104, 1.07
No. of reflections2924
No. of parameters229
No. of restraints11
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.40, 0.35

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
O3—H3O···N20.85 (1)1.82 (2)2.562 (2)145 (2)
O4—H4O···O3i0.85 (1)1.85 (1)2.698 (2)175 (2)
N1—H1N···O1ii0.85 (1)2.05 (1)2.897 (2)171 (2)
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y1/2, z+3/2.
 

Acknowledgements

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02-03–2031) for supporting this study.

References

First citationAli, M. H., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1821–o1822.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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