4-{3-[Hydr­oxy(phen­yl)meth­yl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl}benzene­sulfonamide

Akkurt, M.; Çelik, Í.; Cihan, G.; Çapan, G.; Büyükgüngör, O.

doi:10.1107/S1600536810011402

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o974-o975

doi:10.1107/S1600536810011402

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4-{3-[Hydroxy(phenyl)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl}benzenesulfonamide

Mehmet Akkurt,^a ^* Ísmail Çelik,^b Gökçe Cihan,^c Gültaze Çapan ^c and Orhan Büyükgüngör ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Istanbul, 34116 Beyazıt, Istanbul, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 23 March 2010; accepted 25 March 2010; online 27 March 2010)

In the title compound, C₁₅H₁₄N₄O₃S₂, the hydroxy group is disordered over two positions with occupancies of 0.619 (5) and 0.381 (5). The benzene ring attached to the heterocycle makes a dihedral angle of 86.92 (9)° with respect to the best plane through the five-membered ring. The crystal packing is stabilized by intermolecular O—H⋯O, N—H⋯S, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds, and N—H⋯π and C—H⋯π interactions.

Related literature

For the pharmacological activity of functionalized 1,2,4-triazoles, see: De La Rosa et al. (2006 ); Mavrova et al. (2009 ); Shiradkar et al. (2007 ). For annular tautomerism in 1,2,4-triazoles in the solid state and in solution, see: Buzykin et al. (2008 ); Dolzhenko et al. (2010 ). Two tautomeric fothione (C=S)r.m.s. for 3(5)-thioxo-1,2,4-triazoles may exist in the solid state. For the evidence for the thione (C=S) form, see: Karayel et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₄N₄O₃S₂
M_r = 362.44
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.2498 (5) Å
b = 13.5167 (7) Å
c = 14.2522 (7) Å
V = 1589.26 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.62 × 0.48 × 0.36 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.815, T_max = 0.879
8693 measured reflections
3666 independent reflections
3050 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.066
S = 1.01
3666 reflections
245 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1538 Freidel pairs
Flack parameter: 0.14 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O3ⁱ	0.82	2.35	2.973 (3)	134
N2—H2⋯S1ⁱⁱ	0.86	2.46	3.2744 (15)	158
N4—H4A⋯N1ⁱⁱⁱ	0.88 (2)	2.18 (2)	3.052 (2)	171 (2)
C6—H6⋯O2^iv	0.93	2.57	3.442 (2)	155
C12—H12⋯N1^v	0.93	2.59	3.499 (2)	165
C15—H15⋯O2^iv	0.93	2.48	3.2805 (19)	145
C2—H2A⋯Cg3^vi	0.93	2.90	3.502 (2)	124
N4—H4B⋯Cg2ⁱⁱⁱ	0.85 (2)	2.67 (2)	3.218 (2)	123 (2)
C14—H14⋯Cg2^vii	0.93	2.83	3.463 (2)	126
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) x+1, y, z; (vi) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (vii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011402/bt5224sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810011402/bt5224Isup2.hkl

checkCIF report

Comment top

Functionalized 1,2,4-triazoles have attracted intense research interest after the discovery that triazole have a wide range of pharmacological properties such as antiviral (De La Rosa et al., 2006), anticancer (Mavrova et al., 2009) and antimycobacterial activity (Shiradkar et al., 2007).

Previous reports have also dealt with the annular tautomerism encountered in 1,2,4-triazoles in the solid state and in solution (Buzykin et al., 2008; Dolzhenko et al., 2010). For 3(5)-thioxo-1,2,4-triazoles, two tautomeric forms may exist in the solid state: the thione (C=S) and the thiol (SH), where the former has been supported by a recent X-ray diffraction study (Karayel et al., 2007). In this context, we prepared the title compound to determine its pharmacological potential and the preferred tautomeric form in the solid state.

The title molecule (Fig. 1) the aromatic rings (C1–C6 and C10–C15) are oriented at angles of 73.79 (10) and 86.92 (9)° with respect to the best plane through the five-membered ring. The dihedral angle between the two six-membered rings is 47.58 (9)°.

In the structure, the molecules are linked by intermolecular O—H···O, N—H···S, N—H···N, C—H···O and C—H···N hydrogen bonds (Table 1, Fig. 2), and N—H···π and C—H···π interations (Table 1). In addition, there is also a weak S2—O3···Cg1 (-1+x, y, z) interaction [(S2)O3···Cg1 = 3.1082 (17) Å, S2—O3···Cg1 = 150.21 (9) °, where Cg1 is a centroid of the ring N1–N3/C8/C9].

Related literature top

For the pharmacological activity of functionalized 1,2,4-triazoles, see: De La Rosa et al. (2006); Mavrova et al. (2009); Shiradkar et al. (2007). For annular tautomerism in 1,2,4-triazoles in the solid state and in solution, see: Buzykin et al. (2008); Dolzhenko et al. (2010). Two tautomeric fothione (C=S)r.m.s. for 3(5)-thioxo-1,2,4-triazoles may exist in the solid state. For the evidence for the thione (C=S) form, see: Karayel et al. (2007).

Experimental top

A mixture of 1-[2-[hydroxy(phenyl)acetyl]]-4-(4-sulfamoylphenyl)-3-thiosemicarbazide (0.005 mol) and 2 N NaOH (20 ml) was heated on a water bath for 3 h. After cooling, the reaction mixture was acidified by the addition of HCl (% 12.5). The precipitate thus obtained was filtered, washed with water and recrystallized from aqueous ethanol.[Yield: 80.2 %, m.p.: 523-526 K]. IR (KBr) ν = 3518, 3437, 3346 (O—H, N—H), 1593 (C=N), 1342, 1154 (SO₂) cm^-1. ¹H-NMR (DMSO-d₆, 500 MHz) δ = 5.62 (1H, d, J=3.0 Hz, CHOH), 6.34 (1H, d, J=4.8 Hz, CHOH), 7.17-7.19 (2H, m, Ar—H), 7.22-7.25 (3H, m, Ar—H), 7.41 (2H, d, J=7.90 Hz, Ar—H), 7.52 (2H, s, SO₂NH₂), 7.87 (2H, d, J=8.54 Hz, Ar—H), 13.91 (1H, s, NH). Analysis calculated for C₁₅H₁₄N₄O₃S₂ : C 49.71, H 3.89, N 15.46, S 17.69 %. Found : C 49.47, H 3.72, N 15.26, S 17.94 %.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. The minor occupied sites of the disordered atoms have been omitted for clarity.
	Fig. 2. View down the a axis of the packing and hydrogen bonding interactions of the title compound. All hydrogen atoms not involved in hydrogen bonding and the minor occupied sites of the disordered atoms have been omitted for clarity.

4-{3-[Hydroxy(phenyl)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4- triazol-4-yl}benzenesulfonamide top

Crystal data top

C₁₅H₁₄N₄O₃S₂	F(000) = 752
M_r = 362.44	D_x = 1.515 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14591 reflections
a = 8.2498 (5) Å	θ = 1.4–28.0°
b = 13.5167 (7) Å	µ = 0.36 mm⁻¹
c = 14.2522 (7) Å	T = 296 K
V = 1589.26 (15) Å³	Prism, colourless
Z = 4	0.62 × 0.48 × 0.36 mm

Data collection top

Stoe IPDS 2 diffractometer	3666 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3050 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.036
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.1°
ω scans	h = −10→10
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→16
T_min = 0.815, T_max = 0.879	l = −16→17
8693 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0413P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
3666 reflections	Δρ_max = 0.22 e Å⁻³
245 parameters	Δρ_min = −0.22 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1538 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (5)

Crystal data top

C₁₅H₁₄N₄O₃S₂	V = 1589.26 (15) Å³
M_r = 362.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.2498 (5) Å	µ = 0.36 mm⁻¹
b = 13.5167 (7) Å	T = 296 K
c = 14.2522 (7) Å	0.62 × 0.48 × 0.36 mm

Data collection top

Stoe IPDS 2 diffractometer	3666 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3050 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.879	R_int = 0.036
8693 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	Δρ_max = 0.22 e Å⁻³
S = 1.01	Δρ_min = −0.22 e Å⁻³
3666 reflections	Absolute structure: Flack (1983), 1538 Freidel pairs
245 parameters	Absolute structure parameter: 0.14 (5)
4 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.17287 (5)	0.71648 (3)	0.41130 (3)	0.0371 (1)
S2	0.79576 (4)	0.40875 (3)	0.33694 (3)	0.0315 (1)
O1A	0.2506 (3)	0.4120 (2)	0.6848 (2)	0.0621 (9)	0.620 (4)
O2	0.92661 (14)	0.43807 (13)	0.39572 (10)	0.0510 (5)
O3	0.77632 (18)	0.30741 (11)	0.31372 (14)	0.0592 (5)
N1	−0.03407 (16)	0.55833 (11)	0.60444 (10)	0.0327 (4)
N2	−0.01523 (16)	0.63968 (11)	0.54897 (10)	0.0317 (4)
N3	0.18483 (14)	0.54616 (10)	0.51694 (9)	0.0270 (3)
N4	0.81784 (19)	0.46661 (14)	0.23974 (11)	0.0406 (5)
C1	−0.03337 (19)	0.35747 (13)	0.66854 (13)	0.0334 (5)
C2	−0.0487 (2)	0.33998 (14)	0.76345 (13)	0.0382 (5)
C3	−0.1902 (3)	0.29833 (14)	0.79838 (14)	0.0463 (6)
C4	−0.3154 (2)	0.27399 (15)	0.73879 (17)	0.0496 (6)
C5	−0.2995 (2)	0.29076 (16)	0.64419 (16)	0.0504 (6)
C6	−0.1595 (2)	0.33125 (15)	0.60919 (14)	0.0426 (6)
C7A	0.1213 (9)	0.4010 (5)	0.6305 (6)	0.0333 (16)	0.620 (4)
C8	0.08859 (17)	0.50199 (12)	0.58420 (12)	0.0295 (4)
C9	0.11550 (16)	0.63506 (12)	0.49321 (12)	0.0282 (4)
C10	0.33246 (16)	0.50982 (11)	0.47478 (11)	0.0264 (4)
C11	0.47832 (19)	0.53833 (15)	0.51248 (13)	0.0369 (5)
C12	0.62079 (19)	0.50687 (15)	0.47033 (14)	0.0379 (5)
C13	0.61324 (17)	0.44786 (13)	0.39193 (12)	0.0289 (4)
C14	0.46561 (18)	0.41826 (14)	0.35441 (12)	0.0353 (5)
C15	0.32367 (18)	0.45127 (13)	0.39608 (13)	0.0352 (5)
C7B	0.1184 (15)	0.4081 (11)	0.6206 (12)	0.055 (5)	0.380 (4)
O1B	0.2021 (5)	0.3451 (3)	0.5701 (3)	0.0600 (16)	0.380 (4)
H2A	0.03560	0.35610	0.80400	0.0460*
H3	−0.20040	0.28680	0.86240	0.0560*
H2	−0.08080	0.68910	0.54970	0.0380*
H4A	0.734 (3)	0.4531 (19)	0.2033 (17)	0.0660*
H4B	0.848 (3)	0.5258 (14)	0.251 (2)	0.0660*
H4	−0.41020	0.24640	0.76250	0.0600*
H6	−0.14900	0.34120	0.54490	0.0510*
H7A	0.15510	0.35690	0.57950	0.0400*	0.620 (4)
H11	0.48150	0.57820	0.56560	0.0440*
H12	0.72060	0.52560	0.49490	0.0450*
H14	0.46200	0.37700	0.30220	0.0420*
H15	0.22350	0.43400	0.37100	0.0420*
H5	−0.38390	0.27460	0.60370	0.0600*
H1A	0.26160	0.36280	0.71790	0.0930*	0.620 (4)
H1B	0.23780	0.30130	0.60420	0.0890*	0.380 (4)
H7B	0.19040	0.42150	0.67380	0.0660*	0.380 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0329 (2)	0.0357 (2)	0.0426 (2)	−0.0029 (2)	0.0009 (2)	0.0101 (2)
S2	0.0211 (2)	0.0390 (2)	0.0344 (2)	0.0051 (2)	0.0029 (1)	0.0016 (2)
O1A	0.0366 (11)	0.0597 (16)	0.090 (2)	−0.0082 (10)	−0.0184 (11)	0.0367 (15)
O2	0.0231 (5)	0.0929 (12)	0.0369 (7)	0.0062 (6)	−0.0020 (5)	0.0003 (7)
O3	0.0482 (7)	0.0366 (7)	0.0928 (12)	0.0067 (6)	0.0273 (8)	−0.0050 (8)
N1	0.0296 (6)	0.0344 (8)	0.0341 (7)	0.0042 (5)	0.0055 (5)	0.0036 (6)
N2	0.0286 (6)	0.0291 (7)	0.0375 (8)	0.0053 (5)	0.0045 (5)	0.0016 (6)
N3	0.0223 (5)	0.0278 (6)	0.0310 (7)	0.0012 (5)	0.0042 (5)	−0.0001 (5)
N4	0.0343 (7)	0.0527 (9)	0.0349 (8)	0.0026 (7)	0.0023 (6)	0.0022 (7)
C1	0.0311 (7)	0.0298 (8)	0.0392 (9)	0.0017 (6)	0.0023 (7)	0.0063 (8)
C2	0.0401 (9)	0.0372 (9)	0.0373 (9)	0.0029 (7)	−0.0039 (7)	0.0033 (8)
C3	0.0568 (11)	0.0421 (10)	0.0400 (10)	0.0060 (9)	0.0142 (9)	0.0081 (8)
C4	0.0392 (9)	0.0459 (11)	0.0637 (13)	−0.0063 (8)	0.0146 (9)	0.0049 (10)
C5	0.0405 (9)	0.0509 (11)	0.0598 (13)	−0.0063 (9)	−0.0057 (9)	−0.0014 (10)
C6	0.0446 (10)	0.0467 (11)	0.0366 (10)	−0.0007 (8)	−0.0020 (8)	0.0039 (8)
C7A	0.036 (3)	0.019 (2)	0.045 (3)	0.0050 (18)	0.006 (2)	0.015 (2)
C8	0.0253 (6)	0.0313 (8)	0.0318 (8)	0.0009 (5)	0.0035 (6)	0.0015 (7)
C9	0.0245 (6)	0.0292 (8)	0.0310 (8)	−0.0009 (6)	−0.0009 (6)	−0.0025 (7)
C10	0.0212 (6)	0.0271 (7)	0.0308 (7)	0.0014 (5)	0.0036 (5)	0.0016 (6)
C11	0.0278 (7)	0.0468 (10)	0.0362 (9)	0.0000 (7)	−0.0034 (6)	−0.0125 (8)
C12	0.0221 (7)	0.0498 (10)	0.0417 (10)	0.0002 (6)	−0.0043 (6)	−0.0110 (8)
C13	0.0221 (6)	0.0331 (8)	0.0315 (8)	0.0020 (5)	0.0029 (5)	0.0017 (7)
C14	0.0266 (7)	0.0436 (10)	0.0358 (9)	−0.0003 (7)	0.0021 (6)	−0.0123 (8)
C15	0.0215 (6)	0.0425 (9)	0.0417 (9)	−0.0028 (6)	0.0005 (6)	−0.0104 (8)
C7B	0.019 (5)	0.084 (11)	0.063 (8)	0.008 (5)	0.008 (4)	0.007 (7)
O1B	0.069 (3)	0.044 (2)	0.067 (3)	0.0257 (19)	0.044 (2)	0.0191 (19)

Geometric parameters (Å, º) top

S1—C9	1.6727 (17)	C3—C4	1.377 (3)
S2—O2	1.4227 (14)	C4—C5	1.374 (3)
S2—O3	1.4183 (16)	C5—C6	1.372 (3)
S2—N4	1.6012 (17)	C7A—C8	1.540 (7)
S2—C13	1.7779 (15)	C7B—C8	1.393 (15)
O1A—C7A	1.326 (8)	C10—C11	1.373 (2)
O1B—C7B	1.312 (16)	C10—C15	1.375 (2)
O1A—H1A	0.8200	C11—C12	1.387 (2)
O1B—H1B	0.8200	C12—C13	1.374 (3)
N1—C8	1.299 (2)	C13—C14	1.389 (2)
N1—N2	1.363 (2)	C14—C15	1.387 (2)
N2—C9	1.341 (2)	C2—H2A	0.9300
N3—C8	1.381 (2)	C3—H3	0.9300
N3—C9	1.373 (2)	C4—H4	0.9300
N3—C10	1.4442 (18)	C5—H5	0.9300
N2—H2	0.8600	C6—H6	0.9300
N4—H4A	0.88 (2)	C7A—H7A	0.9800
N4—H4B	0.85 (2)	C7B—H7B	0.9800
C1—C2	1.379 (3)	C11—H11	0.9300
C1—C7A	1.506 (8)	C12—H12	0.9300
C1—C6	1.387 (2)	C14—H14	0.9300
C1—C7B	1.582 (14)	C15—H15	0.9300
C2—C3	1.388 (3)

S1···N2ⁱ	3.2744 (15)	C8···O2^xii	3.122 (2)
S1···O3ⁱⁱ	3.460 (2)	C9···O2^xii	3.384 (2)
S1···H2Aⁱⁱⁱ	3.0100	C10···O1A	3.341 (3)
S1···H1Aⁱⁱⁱ	3.0100	C10···O1B	2.821 (4)
S1···H2ⁱ	2.4600	C12···C6^v	3.583 (3)
S1···H4^iv	3.0700	C13···C2ⁱⁱⁱ	3.444 (3)
S2···H6^v	3.1300	C14···C6^vi	3.565 (3)
S2···H1B^vi	3.0000	C14···C5^vi	3.573 (3)
O1A···N3	3.051 (3)	C14···C2ⁱⁱⁱ	3.582 (3)
O1A···C10	3.341 (3)	C15···O1B	3.036 (5)
O1A···O3^vii	2.973 (3)	C15···C5^vi	3.473 (3)
O1B···O3^vii	2.714 (4)	C15···O2^xii	3.2805 (19)
O1B···C15	3.036 (5)	C1···H4A^x	3.09 (3)
O1B···N3	2.825 (4)	C2···H1A	2.6600
O1B···C10	2.821 (4)	C2···H4B^x	3.07 (2)
O2···N3^v	3.1076 (19)	C2···H14^vii	3.0800
O2···C15^v	3.2805 (19)	C3···H14^vii	3.0400
O2···C8^v	3.122 (2)	C3···H4B^x	2.79 (2)
O2···C9^v	3.384 (2)	C4···H4B^x	2.725 (19)
O3···C7A^vi	3.194 (7)	C5···H15^vii	3.0500
O3···C1^vi	3.400 (2)	C5···H4B^x	2.94 (2)
O3···C7B^vi	3.326 (15)	C8···H6	2.9800
O3···O1B^vi	2.714 (4)	C9···H3^xiii	2.9900
O3···S1^viii	3.460 (2)	C10···H7A	2.9400
O3···O1A^vi	2.973 (3)	H1A···S1^x	3.0100
O1A···H2A	2.5700	H1A···C2	2.6600
O1B···H6	2.9200	H1A···H2A	2.2300
O2···H12	2.5100	H1A···O3^vii	2.3500
O2···H15^v	2.4800	H1B···O3^vii	1.9000
O2···H6^v	2.5700	H1B···S2^vii	3.0000
O3···H7A^vi	2.8700	H2···S1^xi	2.4600
O3···H14	2.7600	H2A···O1A	2.5700
O3···H1B^vi	1.9000	H2A···S1^x	3.0100
O3···H1A^vi	2.3500	H2A···H1A	2.2300
O3···H4^ix	2.9000	H2A···H7B	2.4200
N1···N3	2.2008 (18)	H3···C9^xiv	2.9900
N1···C6	3.240 (2)	H4···O3^xv	2.9000
N1···N4^x	3.052 (2)	H4···S1^xvi	3.0700
N2···N3	2.1285 (19)	H4A···C1ⁱⁱⁱ	3.09 (3)
N2···S1^xi	3.2744 (15)	H4A···N1ⁱⁱⁱ	2.18 (2)
N3···O1B	2.825 (4)	H4B···C2ⁱⁱⁱ	3.07 (2)
N3···N2	2.1285 (19)	H4B···C3ⁱⁱⁱ	2.79 (2)
N3···O1A	3.051 (3)	H4B···C5ⁱⁱⁱ	2.94 (2)
N3···O2^xii	3.1076 (19)	H4B···C4ⁱⁱⁱ	2.725 (19)
N4···C2ⁱⁱⁱ	3.447 (3)	H6···S2^xii	3.1300
N4···N1ⁱⁱⁱ	3.052 (2)	H6···O2^xii	2.5700
N4···C3ⁱⁱⁱ	3.450 (3)	H6···C8	2.9800
N1···H12^xii	2.5900	H6···H7A	2.5700
N1···H4A^x	2.18 (2)	H6···O1B	2.9200
N2···H12^xii	2.7800	H7A···C10	2.9400
C1···O3^vii	3.400 (2)	H7A···H6	2.5700
C2···C13^x	3.444 (3)	H7A···O3^vii	2.8700
C2···N4^x	3.447 (3)	H7B···H2A	2.4200
C2···C14^x	3.582 (3)	H12···N2^v	2.7800
C3···N4^x	3.450 (3)	H12···N1^v	2.5900
C5···C15^vii	3.473 (3)	H12···O2	2.5100
C5···C14^vii	3.573 (3)	H14···C2^vi	3.0800
C6···C12^xii	3.583 (3)	H14···O3	2.7600
C6···C14^vii	3.565 (3)	H14···C3^vi	3.0400
C6···N1	3.240 (2)	H15···C5^vi	3.0500
C7A···O3^vii	3.194 (7)	H15···O2^xii	2.4800
C7B···O3^vii	3.326 (15)

O2—S2—O3	119.49 (10)	N3—C8—C7A	125.5 (3)
O2—S2—N4	106.68 (9)	S1—C9—N2	127.62 (12)
O2—S2—C13	107.47 (8)	S1—C9—N3	129.04 (11)
O3—S2—N4	106.42 (11)	N2—C9—N3	103.28 (14)
O3—S2—C13	107.11 (9)	N3—C10—C11	118.74 (14)
N4—S2—C13	109.42 (8)	C11—C10—C15	121.81 (14)
C7A—O1A—H1A	109.00	N3—C10—C15	119.39 (12)
C7B—O1B—H1B	109.00	C10—C11—C12	119.16 (17)
N2—N1—C8	104.79 (13)	C11—C12—C13	119.46 (15)
N1—N2—C9	113.44 (14)	S2—C13—C12	119.51 (11)
C9—N3—C10	123.12 (13)	S2—C13—C14	119.16 (13)
C8—N3—C9	108.06 (12)	C12—C13—C14	121.33 (14)
C8—N3—C10	128.82 (13)	C13—C14—C15	118.87 (16)
N1—N2—H2	123.00	C10—C15—C14	119.35 (14)
C9—N2—H2	123.00	C3—C2—H2A	120.00
H4A—N4—H4B	122 (2)	C1—C2—H2A	120.00
S2—N4—H4A	108.6 (16)	C2—C3—H3	120.00
S2—N4—H4B	109.2 (19)	C4—C3—H3	120.00
C2—C1—C7B	124.8 (6)	C3—C4—H4	120.00
C2—C1—C7A	119.9 (3)	C5—C4—H4	120.00
C6—C1—C7A	121.1 (4)	C6—C5—H5	120.00
C6—C1—C7B	116.2 (6)	C4—C5—H5	120.00
C2—C1—C6	119.05 (16)	C5—C6—H6	120.00
C1—C2—C3	119.89 (17)	C1—C6—H6	120.00
C2—C3—C4	120.42 (19)	O1A—C7A—H7A	106.00
C3—C4—C5	119.63 (17)	C8—C7A—H7A	106.00
C4—C5—C6	120.21 (18)	C1—C7A—H7A	106.00
C1—C6—C5	120.78 (19)	C8—C7B—H7B	103.00
O1A—C7A—C8	107.0 (5)	C1—C7B—H7B	103.00
O1A—C7A—C1	121.0 (6)	O1B—C7B—H7B	103.00
C1—C7A—C8	110.6 (5)	C10—C11—H11	120.00
O1B—C7B—C8	118.7 (12)	C12—C11—H11	120.00
C1—C7B—C8	114.5 (8)	C11—C12—H12	120.00
O1B—C7B—C1	111.9 (10)	C13—C12—H12	120.00
N1—C8—N3	110.41 (14)	C15—C14—H14	121.00
N1—C8—C7A	124.1 (3)	C13—C14—H14	121.00
N3—C8—C7B	123.4 (6)	C10—C15—H15	120.00
N1—C8—C7B	126.1 (6)	C14—C15—H15	120.00

O2—S2—C13—C12	7.66 (18)	C2—C1—C6—C5	1.6 (3)
O2—S2—C13—C14	−172.54 (15)	C7A—C1—C6—C5	179.4 (3)
O3—S2—C13—C12	137.22 (16)	C2—C1—C7A—O1A	8.1 (7)
O3—S2—C13—C14	−42.98 (18)	C2—C1—C7A—C8	−118.0 (4)
N4—S2—C13—C12	−107.81 (16)	C6—C1—C7A—O1A	−169.6 (4)
N4—S2—C13—C14	71.99 (16)	C6—C1—C7A—C8	64.3 (6)
C8—N1—N2—C9	0.93 (18)	C1—C2—C3—C4	0.2 (3)
N2—N1—C8—N3	0.02 (18)	C2—C3—C4—C5	0.3 (3)
N2—N1—C8—C7A	179.2 (4)	C3—C4—C5—C6	0.2 (3)
N1—N2—C9—S1	175.96 (12)	C4—C5—C6—C1	−1.2 (3)
N1—N2—C9—N3	−1.44 (18)	O1A—C7A—C8—N1	−109.8 (5)
C9—N3—C8—N1	−0.90 (18)	O1A—C7A—C8—N3	69.3 (6)
C9—N3—C8—C7A	179.9 (4)	C1—C7A—C8—N1	23.9 (7)
C10—N3—C8—N1	179.74 (14)	C1—C7A—C8—N3	−157.0 (3)
C10—N3—C8—C7A	0.6 (4)	N3—C10—C11—C12	−177.57 (16)
C8—N3—C9—S1	−175.99 (13)	C15—C10—C11—C12	−0.3 (3)
C8—N3—C9—N2	1.37 (17)	N3—C10—C15—C14	178.55 (15)
C10—N3—C9—S1	3.4 (2)	C11—C10—C15—C14	1.3 (3)
C10—N3—C9—N2	−179.23 (13)	C10—C11—C12—C13	−0.1 (3)
C8—N3—C10—C11	−94.4 (2)	C11—C12—C13—S2	179.21 (15)
C8—N3—C10—C15	88.3 (2)	C11—C12—C13—C14	−0.6 (3)
C9—N3—C10—C11	86.3 (2)	S2—C13—C14—C15	−178.22 (14)
C9—N3—C10—C15	−90.99 (19)	C12—C13—C14—C15	1.6 (3)
C6—C1—C2—C3	−1.2 (3)	C13—C14—C15—C10	−1.9 (3)
C7A—C1—C2—C3	−178.9 (3)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1/2, −y+1, z−1/2; (iv) −x−1/2, −y+1, z−1/2; (v) x+1, y, z; (vi) x+1/2, −y+1/2, −z+1; (vii) x−1/2, −y+1/2, −z+1; (viii) −x+1, y−1/2, −z+1/2; (ix) x+3/2, −y+1/2, −z+1; (x) −x+1/2, −y+1, z+1/2; (xi) x−1/2, −y+3/2, −z+1; (xii) x−1, y, z; (xiii) −x, y+1/2, −z+3/2; (xiv) −x, y−1/2, −z+3/2; (xv) x−3/2, −y+1/2, −z+1; (xvi) −x−1/2, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O3^vii	0.82	2.35	2.973 (3)	134
N2—H2···S1^xi	0.86	2.46	3.2744 (15)	158
N4—H4A···N1ⁱⁱⁱ	0.88 (2)	2.18 (2)	3.052 (2)	171 (2)
C2—H2A···O1A	0.93	2.57	2.881 (3)	100
C6—H6···O2^xii	0.93	2.57	3.442 (2)	155
C12—H12···O2	0.93	2.51	2.892 (2)	105
C12—H12···N1^v	0.93	2.59	3.499 (2)	165
C15—H15···O2^xii	0.93	2.48	3.2805 (19)	145
C2—H2A···Cg3^x	0.93	2.90	3.502 (2)	124
N4—H4B···Cg2ⁱⁱⁱ	0.85 (2)	2.67 (2)	3.218 (2)	123 (2)
C14—H14···Cg2^vi	0.93	2.83	3.463 (2)	126

Symmetry codes: (iii) −x+1/2, −y+1, z−1/2; (v) x+1, y, z; (vi) x+1/2, −y+1/2, −z+1; (vii) x−1/2, −y+1/2, −z+1; (x) −x+1/2, −y+1, z+1/2; (xi) x−1/2, −y+3/2, −z+1; (xii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₄O₃S₂
M_r	362.44
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.2498 (5), 13.5167 (7), 14.2522 (7)
V (Å³)	1589.26 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.62 × 0.48 × 0.36

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.815, 0.879
No. of measured, independent and observed [I > 2σ(I)] reflections	8693, 3666, 3050
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.066, 1.01
No. of reflections	3666
No. of parameters	245
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22
Absolute structure	Flack (1983), 1538 Freidel pairs
Absolute structure parameter	0.14 (5)

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O3ⁱ	0.82	2.35	2.973 (3)	134
N2—H2···S1ⁱⁱ	0.86	2.46	3.2744 (15)	158
N4—H4A···N1ⁱⁱⁱ	0.88 (2)	2.18 (2)	3.052 (2)	171 (2)
C2—H2A···O1A	0.93	2.57	2.881 (3)	100
C6—H6···O2^iv	0.93	2.57	3.442 (2)	155
C12—H12···O2	0.93	2.51	2.892 (2)	105
C12—H12···N1^v	0.93	2.59	3.499 (2)	165
C15—H15···O2^iv	0.93	2.48	3.2805 (19)	145
C2—H2A···Cg3^vi	0.93	2.90	3.502 (2)	124
N4—H4B···Cg2ⁱⁱⁱ	0.85 (2)	2.67 (2)	3.218 (2)	123 (2)
C14—H14···Cg2^vii	0.93	2.83	3.463 (2)	126

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) −x+1/2, −y+1, z−1/2; (iv) x−1, y, z; (v) x+1, y, z; (vi) −x+1/2, −y+1, z+1/2; (vii) x+1/2, −y+1/2, −z+1.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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Volume 66| Part 4| April 2010| Pages o974-o975

doi:10.1107/S1600536810011402

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

4-{3-[Hydr­­oxy(phen­yl)meth­yl]-5-thioxo-4,5-di­hydro-1H-1,2,4-triazol-4-yl}benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-{3-[Hydroxy(phenyl)methyl]-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl}benzenesulfonamide