N′-(2,5-Dihydroxy­benzyl­idene)benzene­sulfonohydrazide

Ali, H.M.; Yusnita, J.; Rizal, M.R.; Ng, S.W.

doi:10.1107/S1600536808002225

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o522

doi:10.1107/S1600536808002225

Open

access

N′-(2,5-Dihydroxybenzylidene)benzenesulfonohydrazide

Hapipah M. Ali,^a Juahir Yusnita,^a Mohd. Razali Rizal ^a and Seik Weng Ng ^a ^*

^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⋯O_hydroxy and N—H⋯O_sulfonyl 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 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₄S
M_r = 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)
R_int = 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
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002225/wn2236sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002225/wn2236Isup2.hkl

checkCIF report

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.

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

	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.
	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

C₁₃H₁₂N₂O₄S	F(000) = 608
M_r = 292.31	D_x = 1.525 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9918 reflections
a = 12.5814 (2) Å	θ = 5.0–63.2°
b = 7.1601 (1) Å	µ = 0.27 mm⁻¹
c = 14.6727 (2) Å	T = 128 K
β = 105.540 (1)°	Block, yellow
V = 1273.46 (3) Å³	0.65 × 0.33 × 0.29 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2684 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ϕ and ω scans	h = −16→16
16406 measured reflections	k = −9→9
2924 independent reflections	l = −18→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	All H-atom parameters refined
S = 1.07	w = 1/[σ²(F_o²) + (0.0666P)² + 0.482P] where P = (F_o² + 2F_c²)/3
2924 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.40 e Å⁻³
11 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₄S	V = 1273.46 (3) Å³
M_r = 292.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.5814 (2) Å	µ = 0.27 mm⁻¹
b = 7.1601 (1) Å	T = 128 K
c = 14.6727 (2) Å	0.65 × 0.33 × 0.29 mm
β = 105.540 (1)°

Data collection top

Bruker APEXII diffractometer	2684 reflections with I > 2σ(I)
16406 measured reflections	R_int = 0.023
2924 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	11 restraints
wR(F²) = 0.104	All H-atom parameters refined
S = 1.07	Δρ_max = 0.40 e Å⁻³
2924 reflections	Δρ_min = −0.35 e Å⁻³
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

	x	y	z	U_iso*/U_eq
S1	0.77742 (3)	0.75958 (4)	0.66733 (2)	0.01720 (12)
N1	0.83576 (9)	0.55528 (16)	0.65868 (8)	0.0190 (2)
N2	0.84430 (9)	0.52079 (16)	0.56754 (8)	0.0186 (2)
O1	0.77923 (9)	0.76844 (15)	0.76588 (7)	0.0245 (2)
O2	0.83351 (8)	0.89724 (14)	0.62689 (7)	0.0249 (2)
O3	0.85080 (9)	0.64124 (14)	0.40471 (7)	0.0276 (2)
O4	0.91487 (10)	−0.08605 (15)	0.30407 (8)	0.0307 (3)
C1	0.63909 (11)	0.74943 (17)	0.59938 (9)	0.0164 (3)
C2	0.61433 (11)	0.7976 (2)	0.50377 (9)	0.0198 (3)
C3	0.50524 (12)	0.7887 (2)	0.44977 (10)	0.0228 (3)
C4	0.42314 (12)	0.7347 (2)	0.49182 (11)	0.0241 (3)
C5	0.44840 (12)	0.6872 (2)	0.58702 (11)	0.0242 (3)
C6	0.55757 (11)	0.69292 (19)	0.64210 (9)	0.0204 (3)
C7	0.86202 (10)	0.35212 (19)	0.54498 (9)	0.0182 (3)
C8	0.87129 (10)	0.31449 (19)	0.44957 (9)	0.0175 (3)
C9	0.88699 (11)	0.12938 (19)	0.42327 (10)	0.0199 (3)
C10	0.89662 (11)	0.08955 (19)	0.33332 (10)	0.0220 (3)
C11	0.88899 (13)	0.2343 (2)	0.26805 (10)	0.0248 (3)
C12	0.87375 (12)	0.4168 (2)	0.29252 (10)	0.0248 (3)
C13	0.86505 (11)	0.45797 (19)	0.38301 (9)	0.0203 (3)
H3O	0.8478 (19)	0.650 (3)	0.4615 (8)	0.052 (6)*
H4O	0.8920 (18)	−0.168 (3)	0.3363 (15)	0.050 (6)*
H1N	0.8083 (15)	0.470 (2)	0.6862 (13)	0.034 (5)*
H2	0.6718 (11)	0.834 (2)	0.4758 (12)	0.026 (4)*
H3	0.4885 (15)	0.824 (3)	0.3850 (7)	0.031 (5)*
H4	0.3471 (18)	0.729 (3)	0.4543 (14)	0.033 (5)*
H5	0.3922 (12)	0.651 (3)	0.6166 (12)	0.032 (5)*
H6	0.5728 (13)	0.657 (2)	0.7068 (7)	0.024 (4)*
H7	0.8721 (15)	0.2494 (17)	0.5872 (10)	0.019 (4)*
H9	0.8924 (15)	0.031 (2)	0.4681 (10)	0.028 (4)*
H11	0.8879 (18)	0.201 (3)	0.2057 (8)	0.045 (6)*
H12	0.8656 (15)	0.515 (2)	0.2476 (11)	0.032 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01696 (19)	0.01935 (18)	0.01461 (19)	−0.00098 (10)	0.00306 (13)	−0.00294 (10)
N1	0.0212 (5)	0.0213 (5)	0.0157 (5)	0.0023 (4)	0.0070 (4)	0.0008 (4)
N2	0.0174 (5)	0.0235 (6)	0.0161 (5)	0.0000 (4)	0.0066 (4)	−0.0005 (4)
O1	0.0261 (5)	0.0312 (6)	0.0144 (5)	0.0025 (4)	0.0025 (4)	−0.0053 (4)
O2	0.0229 (5)	0.0226 (5)	0.0288 (5)	−0.0048 (4)	0.0065 (4)	−0.0010 (4)
O3	0.0434 (6)	0.0195 (5)	0.0232 (5)	0.0037 (4)	0.0147 (5)	0.0033 (4)
O4	0.0461 (7)	0.0225 (5)	0.0318 (6)	−0.0037 (4)	0.0249 (5)	−0.0047 (4)
C1	0.0166 (6)	0.0173 (6)	0.0150 (6)	0.0003 (4)	0.0037 (5)	−0.0022 (4)
C2	0.0210 (6)	0.0231 (6)	0.0164 (6)	0.0009 (5)	0.0069 (5)	−0.0010 (5)
C3	0.0235 (7)	0.0274 (7)	0.0163 (6)	0.0028 (5)	0.0033 (5)	−0.0013 (5)
C4	0.0187 (7)	0.0266 (7)	0.0247 (7)	−0.0007 (5)	0.0020 (6)	−0.0034 (5)
C5	0.0208 (6)	0.0255 (7)	0.0281 (7)	−0.0030 (5)	0.0097 (5)	−0.0006 (6)
C6	0.0225 (6)	0.0219 (6)	0.0176 (6)	−0.0010 (5)	0.0069 (5)	0.0010 (5)
C7	0.0162 (6)	0.0214 (6)	0.0175 (6)	0.0003 (5)	0.0054 (5)	0.0018 (5)
C8	0.0148 (6)	0.0219 (6)	0.0167 (6)	0.0003 (5)	0.0058 (4)	0.0011 (5)
C9	0.0200 (6)	0.0207 (6)	0.0211 (6)	0.0002 (5)	0.0091 (5)	0.0018 (5)
C10	0.0220 (6)	0.0220 (6)	0.0253 (7)	−0.0025 (5)	0.0118 (5)	−0.0027 (5)
C11	0.0286 (7)	0.0300 (7)	0.0187 (7)	−0.0033 (5)	0.0116 (6)	−0.0017 (5)
C12	0.0298 (7)	0.0260 (7)	0.0201 (7)	−0.0009 (6)	0.0095 (5)	0.0051 (5)
C13	0.0202 (6)	0.0200 (6)	0.0214 (7)	0.0011 (5)	0.0071 (5)	0.0010 (5)

Geometric parameters (Å, º) top

S1—O2	1.4304 (10)	C4—C5	1.389 (2)
S1—O1	1.4415 (10)	C4—H4	0.97 (2)
S1—N1	1.6567 (12)	C5—C6	1.395 (2)
S1—C1	1.7602 (13)	C5—H5	0.959 (9)
N1—N2	1.3920 (15)	C6—H6	0.953 (9)
N1—H1N	0.85 (1)	C7—C8	1.4607 (17)
N2—C7	1.2874 (17)	C7—H7	0.948 (9)
O3—C13	1.3733 (16)	C8—C13	1.4051 (18)
O3—H3O	0.85 (1)	C8—C9	1.4090 (18)
O4—C10	1.3677 (16)	C9—C10	1.3870 (19)
O4—H4O	0.85 (1)	C9—H9	0.953 (9)
C1—C2	1.3963 (18)	C10—C11	1.397 (2)
C1—C6	1.3976 (18)	C11—C12	1.382 (2)
C2—C3	1.3904 (19)	C11—H11	0.943 (9)
C2—H2	0.958 (9)	C12—C13	1.3928 (19)
C3—C4	1.392 (2)	C12—H12	0.950 (9)
C3—H3	0.951 (9)

O2—S1—O1	120.59 (6)	C6—C5—H5	118.4 (11)
O2—S1—N1	107.38 (6)	C5—C6—C1	118.40 (12)
O1—S1—N1	103.14 (6)	C5—C6—H6	118.2 (10)
O2—S1—C1	108.44 (6)	C1—C6—H6	123.4 (10)
O1—S1—C1	108.51 (6)	N2—C7—C8	118.90 (12)
N1—S1—C1	108.14 (6)	N2—C7—H7	124.2 (10)
N2—N1—S1	112.33 (9)	C8—C7—H7	116.9 (10)
N2—N1—H1N	118.3 (13)	C13—C8—C9	118.90 (12)
S1—N1—H1N	110.4 (13)	C13—C8—C7	121.83 (12)
C7—N2—N1	118.47 (11)	C9—C8—C7	119.28 (12)
C13—O3—H3O	110.2 (17)	C10—C9—C8	120.55 (12)
C10—O4—H4O	110.5 (16)	C10—C9—H9	119.8 (11)
C2—C1—C6	121.94 (12)	C8—C9—H9	119.6 (11)
C2—C1—S1	118.65 (10)	O4—C10—C9	123.53 (13)
C6—C1—S1	119.40 (10)	O4—C10—C11	116.96 (12)
C3—C2—C1	118.80 (12)	C9—C10—C11	119.50 (13)
C3—C2—H2	120.7 (11)	C12—C11—C10	120.81 (13)
C1—C2—H2	120.5 (11)	C12—C11—H11	121.8 (14)
C2—C3—C4	119.77 (13)	C10—C11—H11	117.1 (14)
C2—C3—H3	118.6 (11)	C11—C12—C13	119.98 (13)
C4—C3—H3	121.6 (11)	C11—C12—H12	121.0 (12)
C5—C4—C3	121.10 (13)	C13—C12—H12	118.9 (12)
C5—C4—H4	119.2 (12)	O3—C13—C12	118.16 (12)
C3—C4—H4	119.7 (12)	O3—C13—C8	121.59 (12)
C4—C5—C6	119.98 (13)	C12—C13—C8	120.25 (12)
C4—C5—H5	121.6 (11)

O2—S1—N1—N2	−50.34 (10)	S1—C1—C6—C5	179.56 (10)
O1—S1—N1—N2	−178.71 (8)	N1—N2—C7—C8	−179.90 (10)
C1—S1—N1—N2	66.48 (10)	N2—C7—C8—C13	2.14 (19)
S1—N1—N2—C7	−163.01 (10)	N2—C7—C8—C9	−177.89 (12)
O2—S1—C1—C2	27.78 (12)	C13—C8—C9—C10	0.28 (19)
O1—S1—C1—C2	160.41 (10)	C7—C8—C9—C10	−179.68 (12)
N1—S1—C1—C2	−88.36 (11)	C8—C9—C10—O4	178.20 (12)
O2—S1—C1—C6	−152.52 (10)	C8—C9—C10—C11	−1.0 (2)
O1—S1—C1—C6	−19.89 (12)	O4—C10—C11—C12	−178.16 (14)
N1—S1—C1—C6	91.34 (11)	C9—C10—C11—C12	1.0 (2)
C6—C1—C2—C3	−0.1 (2)	C10—C11—C12—C13	−0.5 (2)
S1—C1—C2—C3	179.64 (10)	C11—C12—C13—O3	179.51 (13)
C1—C2—C3—C4	0.8 (2)	C11—C12—C13—C8	−0.2 (2)
C2—C3—C4—C5	−0.7 (2)	C9—C8—C13—O3	−179.42 (12)
C3—C4—C5—C6	−0.1 (2)	C7—C8—C13—O3	0.5 (2)
C4—C5—C6—C1	0.8 (2)	C9—C8—C13—C12	0.32 (19)
C2—C1—C6—C5	−0.8 (2)	C7—C8—C13—C12	−179.71 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₄S
M_r	292.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	128
a, b, c (Å)	12.5814 (2), 7.1601 (1), 14.6727 (2)
β (°)	105.540 (1)
V (Å³)	1273.46 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.65 × 0.33 × 0.29

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16406, 2924, 2684
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.104, 1.07
No. of reflections	2924
No. of parameters	229
No. of restraints	11
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+3/2, y−1/2, −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

Ali, 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
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar