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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2067
https://doi.org/10.1107/S1600536812025305

3-(1-Benzo­furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione monohydrate

Hoong-Kun Fun,a*‡ Suhana Arshad,a Nithinchandra,b Balakrishna Kallurayab and Shobhitha Shettyb

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Studies in Chemistry, Mangalore University, Mangalagangothri 574 199, Karnataka, India
*Correspondence e-mail: hkfun@usm.my

(Received 3 June 2012; accepted 4 June 2012; online 13 June 2012)

In the title hydrate, C10H7N3OS·H2O, the essentially planar benzofuran [maximum deviation = 0.006 (1) Å] and 4,5-dihydro-1H-1,2,4-triazole [maximum deviation = 0.007 (1) Å] rings form a dihedral angle of 11.67 (6)°. In the crystal, O—H⋯N, O—H⋯S, N—H⋯O and N—H⋯S hydrogen bonds link the mol­ecules into sheets lying parallel to the bc plane. Aromatic π–π stacking inter­actions [centroid–centroid distances = 3.5078 (8)–3.6113 (8) Å] are also observed.

Related literature

For background to 1,2,4-triazoles, see: Shujuan et al. (2004[Shujuan, S., Hongxiang, L., Gao, Y., Fan, P., Ma, B., Ge, W. & Wang, X. (2004). J. Pharm. Biomed. Anal. 34, 1117-1124.]); Clemons et al. (2004[Clemons, M., Coleman, R. E. & Verma, S. (2004). Cancer Treat. Rev. 30, 325-332.]); Johnston (2002[Johnston, G. A. R. (2002). Curr. Top. Med. Chem. 2, 903-913.]); Wei et al. (2007[Wei, T.-B., Tang, J., Liu, H. & Zhang, Y.-M. (2007). Phosphorus Sulfur Silicon, 182, 1581-1587.]). For related structures, see: Jing et al. (2012[Jing, B., Du, Y.-C. & Zhu, A.-X. (2012). Acta Cryst. E68, o1802.]); Fun et al. (2011[Fun, H.-K., Quah, C. K., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o2413.]); Abdel-Aziz et al. (2011[Abdel-Aziz, H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2675.]). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C10H7N3OS·H2O

  • Mr = 235.26

  • Monoclinic, P 21 /c

  • a = 7.1446 (1) Å

  • b = 8.8075 (1) Å

  • c = 17.3274 (2) Å

  • β = 111.942 (1)°

  • V = 1011.36 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 100 K

  • 0.39 × 0.20 × 0.15 mm
Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.891, Tmax = 0.955

  • 19917 measured reflections

  • 4162 independent reflections

  • 3347 reflections with > I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.108

  • S = 1.07

  • 4162 reflections

  • 153 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1OW⋯N2i 0.90 2.05 2.9135 (14) 160
O1W—H2OW⋯S1ii 0.82 2.46 3.2674 (11) 167
N1—H1N1⋯O1Wiii 0.90 (2) 1.81 (2) 2.7100 (14) 172.6 (19)
N3—H1N3⋯S1iv 0.846 (18) 2.498 (18) 3.3242 (10) 165.7 (16)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [x+1, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025305/hb6837sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025305/hb6837Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025305/hb6837Isup3.cml

checkCIF report


Comment top

The 1,2,4-triazole nucleus has been incorporated into a wide variety of therapeutically interesting compounds. Several compounds containing 1,2,4-triazole rings are well known as drugs. For example, fluconazole is used as an antimicrobial drug (Shujuan et al., 2004), whereas vorozole, letrozole and anastrozole are non-steroidal drugs used for the treatment of cancer (Clemons et al., 2004) and loreclezole is used as an anticonvulsant (Johnston, 2002). Similarly substituted derivatives of triazole possess comprehensive bioactivities such as antimicrobial, anti-inflammatory, analgesic, antihypertensive, anticonvulsant and antiviral activities (Wei et al., 2007). We now report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), consists of one 5-(1-Benzofuran-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione molecule and one water molecule. The benzofuran ring (O1/C3–C10) and the 4,5-dihydro -1H-1,2,4-triazole ring (N1–N3/C1/C2) are essentially planar with maximum deviations of 0.006 (1) Å at atom O1 and 0.007 (1) Å at atom N3, respectively. The dihedral angle between the benzofuran and 4,5-dihydro- 1H-1,2,4-triazole rings is 11.67 (6)°. Bond lengths and angles are within normal ranges and comparable to the related structures (Jing et al., 2012; Fun et al., 2011; Abdel-Aziz et al., 2011).

The crystal packing is shown in Fig. 2. The molecules are linked via O1W—H1OW···N2, O1W—H2OW···S1, N1—H1N1···O1W and N3—H1N3···S1 hydrogen bonds (Table 1) into two-dimensional networks parallel to bc-plane. π–π interactions of Cg1···Cg1 = 3.6113 (8) Å (symmetry code: 1 - x, -y, 1 - z), Cg1···Cg2 = 3.5078 (8) Å (symmetry code: 2 - x, -y, 1 - z), Cg2···Cg3 = 3.5881 (8) Å (symmetry code: 1 - x, -y, 1 - z) and Cg3···Cg2 = 3.6056 (8) Å (symmetry code: 2 - x, -y, 1 - z) further stabilized the crystal structure [Cg1, Cg2 and Cg3 are the centroids of the O1/C3–C5/C10, N1–N3/C1/C2 and C5–C10 rings, respectively].

Related literature top

For background to 1,2,4-triazoles, see: Shujuan et al. (2004); Clemons et al. (2004); Johnston (2002); Wei et al. (2007). For related structures, see: Jing et al. (2012); Fun et al. (2011); Abdel-Aziz et al. (2011). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2-(1-benzofuran-2-ylcarbonyl)hydrazinecarbothioamide (0.01 mol) and 10% KOH (10 ml) was refluxed for 3 h. The mixture was cooled to room temperature and then neutralized by the gradual addition of glacial acetic acid. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Yellow blocks of the title compound were obtained by slow evaporation of the ethanolic solution.

Refinement top

O– and N-bound H atoms were located from a difference Fourier map. O-bound H atoms were fixed at their found positions (O–H = 0.8961 and 0.8208 Å), with Uiso(H) = 1.5 Ueq(O), whereas N-bound H atoms was refined freely [N–H = 0.844 (18) and 0.90 (2) Å]. The remaining H atoms were positioned geometrically [C–H = 0.93 Å] and refined using a riding model with Uiso(H) = 1.2 Ueq(C). In the final refinement, one outlier (1 1 1) was omitted.

Structure description top

The 1,2,4-triazole nucleus has been incorporated into a wide variety of therapeutically interesting compounds. Several compounds containing 1,2,4-triazole rings are well known as drugs. For example, fluconazole is used as an antimicrobial drug (Shujuan et al., 2004), whereas vorozole, letrozole and anastrozole are non-steroidal drugs used for the treatment of cancer (Clemons et al., 2004) and loreclezole is used as an anticonvulsant (Johnston, 2002). Similarly substituted derivatives of triazole possess comprehensive bioactivities such as antimicrobial, anti-inflammatory, analgesic, antihypertensive, anticonvulsant and antiviral activities (Wei et al., 2007). We now report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), consists of one 5-(1-Benzofuran-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione molecule and one water molecule. The benzofuran ring (O1/C3–C10) and the 4,5-dihydro -1H-1,2,4-triazole ring (N1–N3/C1/C2) are essentially planar with maximum deviations of 0.006 (1) Å at atom O1 and 0.007 (1) Å at atom N3, respectively. The dihedral angle between the benzofuran and 4,5-dihydro- 1H-1,2,4-triazole rings is 11.67 (6)°. Bond lengths and angles are within normal ranges and comparable to the related structures (Jing et al., 2012; Fun et al., 2011; Abdel-Aziz et al., 2011).

The crystal packing is shown in Fig. 2. The molecules are linked via O1W—H1OW···N2, O1W—H2OW···S1, N1—H1N1···O1W and N3—H1N3···S1 hydrogen bonds (Table 1) into two-dimensional networks parallel to bc-plane. π–π interactions of Cg1···Cg1 = 3.6113 (8) Å (symmetry code: 1 - x, -y, 1 - z), Cg1···Cg2 = 3.5078 (8) Å (symmetry code: 2 - x, -y, 1 - z), Cg2···Cg3 = 3.5881 (8) Å (symmetry code: 1 - x, -y, 1 - z) and Cg3···Cg2 = 3.6056 (8) Å (symmetry code: 2 - x, -y, 1 - z) further stabilized the crystal structure [Cg1, Cg2 and Cg3 are the centroids of the O1/C3–C5/C10, N1–N3/C1/C2 and C5–C10 rings, respectively].

For background to 1,2,4-triazoles, see: Shujuan et al. (2004); Clemons et al. (2004); Johnston (2002); Wei et al. (2007). For related structures, see: Jing et al. (2012); Fun et al. (2011); Abdel-Aziz et al. (2011). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the b axis. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.
3-(1-Benzofuran-2-yl)-1H-1,2,4-triazole-5(4H)-thione monohydrate top
Crystal data top
C10H7N3OS·H2OF(000) = 488
Mr = 235.26Dx = 1.545 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6273 reflections
a = 7.1446 (1) Åθ = 2.5–33.4°
b = 8.8075 (1) ŵ = 0.31 mm−1
c = 17.3274 (2) ÅT = 100 K
β = 111.942 (1)°Block, yellow
V = 1011.36 (2) Å30.39 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer		4162 independent reflections
Radiation source: fine-focus sealed tube3347 reflections with > I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 34.2°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −11→11
Tmin = 0.891, Tmax = 0.955k = −13→13
19917 measured reflectionsl = −26→27
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.4347P]
where P = (Fo2 + 2Fc2)/3
4162 reflections(Δ/σ)max = 0.001
153 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C10H7N3OS·H2OV = 1011.36 (2) Å3
Mr = 235.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.1446 (1) ŵ = 0.31 mm−1
b = 8.8075 (1) ÅT = 100 K
c = 17.3274 (2) Å0.39 × 0.20 × 0.15 mm
β = 111.942 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		4162 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3347 reflections with > I > 2σ(I)
Tmin = 0.891, Tmax = 0.955Rint = 0.039
19917 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.61 e Å−3
4162 reflectionsΔρmin = −0.31 e Å−3
153 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
xyzUiso*/Ueq
S11.16013 (5)−0.27662 (3)0.789110 (18)0.01410 (8)
O10.76589 (13)0.12211 (10)0.53014 (5)0.01383 (17)
N11.01801 (16)−0.33637 (12)0.62307 (6)0.01333 (19)
N20.91410 (16)−0.27263 (11)0.54676 (6)0.01371 (19)
N30.95013 (15)−0.11026 (11)0.64872 (6)0.01228 (18)
C11.04179 (18)−0.24126 (13)0.68643 (7)0.0121 (2)
C20.87285 (17)−0.13492 (13)0.56444 (7)0.0120 (2)
C30.76153 (17)−0.02501 (13)0.50237 (7)0.0122 (2)
C40.65217 (18)−0.03918 (13)0.41967 (7)0.0139 (2)
H4A0.6284−0.12770.38820.017*
C50.58061 (17)0.11092 (14)0.39077 (7)0.0134 (2)
C60.46309 (19)0.17499 (15)0.31360 (8)0.0169 (2)
H6A0.41260.11570.26580.020*
C70.42492 (19)0.32943 (16)0.31110 (8)0.0185 (2)
H7A0.34740.37410.26060.022*
C80.5000 (2)0.42034 (15)0.38265 (9)0.0193 (2)
H8A0.47100.52360.37840.023*
C90.6168 (2)0.35953 (14)0.45977 (8)0.0175 (2)
H9A0.66750.41890.50750.021*
C100.65281 (18)0.20498 (13)0.46092 (7)0.0128 (2)
O1W0.12342 (14)0.13102 (10)0.11923 (6)0.01697 (18)
H1OW0.08270.16770.06730.025*
H2OW0.05380.18100.13830.025*
H1N11.062 (3)−0.433 (2)0.6261 (12)0.032 (5)*
H1N30.933 (3)−0.032 (2)0.6736 (11)0.016 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01807 (14)0.01305 (13)0.00963 (13)0.00052 (9)0.00341 (10)0.00123 (9)
O10.0168 (4)0.0119 (4)0.0113 (4)0.0021 (3)0.0035 (3)−0.0001 (3)
N10.0172 (5)0.0122 (4)0.0099 (4)0.0022 (3)0.0043 (3)0.0014 (3)
N20.0167 (5)0.0130 (4)0.0103 (4)0.0017 (3)0.0038 (3)0.0009 (3)
N30.0158 (4)0.0110 (4)0.0098 (4)0.0021 (3)0.0044 (3)0.0005 (3)
C10.0137 (5)0.0112 (4)0.0118 (5)0.0005 (4)0.0051 (4)0.0013 (4)
C20.0132 (5)0.0126 (5)0.0100 (5)0.0005 (4)0.0040 (4)0.0004 (4)
C30.0130 (5)0.0121 (5)0.0108 (5)0.0008 (4)0.0036 (4)0.0007 (4)
C40.0152 (5)0.0132 (5)0.0115 (5)0.0006 (4)0.0027 (4)−0.0001 (4)
C50.0123 (5)0.0159 (5)0.0113 (5)0.0007 (4)0.0038 (4)0.0024 (4)
C60.0156 (5)0.0214 (6)0.0120 (5)0.0006 (4)0.0030 (4)0.0029 (4)
C70.0153 (5)0.0224 (6)0.0168 (6)0.0041 (4)0.0049 (4)0.0085 (5)
C80.0187 (5)0.0166 (5)0.0236 (6)0.0048 (4)0.0090 (5)0.0061 (5)
C90.0200 (6)0.0147 (5)0.0182 (6)0.0029 (4)0.0077 (4)0.0010 (4)
C100.0134 (5)0.0135 (5)0.0108 (5)0.0018 (4)0.0037 (4)0.0026 (4)
O1W0.0225 (4)0.0144 (4)0.0136 (4)0.0006 (3)0.0064 (3)0.0009 (3)
Geometric parameters (Å, º) top
S1—C11.6892 (12)C4—H4A0.9300
O1—C101.3784 (14)C5—C101.4003 (17)
O1—C31.3785 (14)C5—C61.4045 (17)
N1—C11.3403 (16)C6—C71.3848 (19)
N1—N21.3715 (14)C6—H6A0.9300
N1—H1N10.90 (2)C7—C81.403 (2)
N2—C21.3112 (15)C7—H7A0.9300
N3—C11.3664 (15)C8—C91.3914 (18)
N3—C21.3718 (15)C8—H8A0.9300
N3—H1N30.844 (18)C9—C101.3840 (17)
C2—C31.4448 (16)C9—H9A0.9300
C3—C41.3575 (16)O1W—H1OW0.8961
C4—C51.4382 (16)O1W—H2OW0.8208
C10—O1—C3105.34 (9)C10—C5—C6118.94 (11)
C1—N1—N2113.03 (10)C10—C5—C4105.90 (10)
C1—N1—H1N1127.4 (13)C6—C5—C4135.16 (12)
N2—N1—H1N1119.6 (13)C7—C6—C5117.72 (12)
C2—N2—N1103.96 (10)C7—C6—H6A121.1
C1—N3—C2107.80 (10)C5—C6—H6A121.1
C1—N3—H1N3125.3 (12)C6—C7—C8121.81 (12)
C2—N3—H1N3126.5 (12)C6—C7—H7A119.1
N1—C1—N3104.16 (10)C8—C7—H7A119.1
N1—C1—S1127.44 (9)C9—C8—C7121.54 (12)
N3—C1—S1128.40 (9)C9—C8—H8A119.2
N2—C2—N3111.04 (10)C7—C8—H8A119.2
N2—C2—C3123.72 (11)C10—C9—C8115.71 (12)
N3—C2—C3125.24 (10)C10—C9—H9A122.1
C4—C3—O1112.58 (10)C8—C9—H9A122.1
C4—C3—C2131.59 (11)O1—C10—C9125.35 (11)
O1—C3—C2115.82 (10)O1—C10—C5110.37 (10)
C3—C4—C5105.81 (10)C9—C10—C5124.28 (11)
C3—C4—H4A127.1H1OW—O1W—H2OW101.1
C5—C4—H4A127.1
C1—N1—N2—C2−0.29 (14)C2—C3—C4—C5−178.79 (12)
N2—N1—C1—N3−0.49 (13)C3—C4—C5—C10−0.85 (13)
N2—N1—C1—S1179.94 (9)C3—C4—C5—C6179.54 (14)
C2—N3—C1—N11.06 (13)C10—C5—C6—C70.09 (18)
C2—N3—C1—S1−179.38 (9)C4—C5—C6—C7179.66 (13)
N1—N2—C2—N30.98 (13)C5—C6—C7—C80.00 (19)
N1—N2—C2—C3−179.39 (11)C6—C7—C8—C90.0 (2)
C1—N3—C2—N2−1.34 (14)C7—C8—C9—C10−0.17 (19)
C1—N3—C2—C3179.04 (11)C3—O1—C10—C9−179.75 (12)
C10—O1—C3—C40.01 (13)C3—O1—C10—C5−0.58 (13)
C10—O1—C3—C2179.45 (10)C8—C9—C10—O1179.33 (11)
N2—C2—C3—C411.6 (2)C8—C9—C10—C50.28 (19)
N3—C2—C3—C4−168.79 (13)C6—C5—C10—O1−179.42 (10)
N2—C2—C3—O1−167.68 (11)C4—C5—C10—O10.90 (13)
N3—C2—C3—O111.90 (17)C6—C5—C10—C9−0.24 (19)
O1—C3—C4—C50.54 (14)C4—C5—C10—C9−179.92 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1OW···N2i0.902.052.9135 (14)160
O1W—H2OW···S1ii0.822.463.2674 (11)167
N1—H1N1···O1Wiii0.90 (2)1.81 (2)2.7100 (14)172.6 (19)
N3—H1N3···S1iv0.846 (18)2.498 (18)3.3242 (10)165.7 (16)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) x+1, −y−1/2, z+1/2; (iv) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC10H7N3OS·H2O
Mr235.26
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)7.1446 (1), 8.8075 (1), 17.3274 (2)
β (°) 111.942 (1)
V (Å3)1011.36 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.31
Crystal size (mm)0.39 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.891, 0.955
No. of measured, independent and
observed [ > I > 2σ(I)] reflections		19917, 4162, 3347
Rint0.039
(sin θ/λ)max (Å−1)0.790
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.108, 1.07
No. of reflections4162
No. of parameters153
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.61, −0.31

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1OW···N2i0.902.052.9135 (14)160
O1W—H2OW···S1ii0.822.463.2674 (11)167
N1—H1N1···O1Wiii0.90 (2)1.81 (2)2.7100 (14)172.6 (19)
N3—H1N3···S1iv0.846 (18)2.498 (18)3.3242 (10)165.7 (16)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z+1; (iii) x+1, −y−1/2, z+1/2; (iv) −x+2, y+1/2, −z+3/2.
 

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award. BK is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for financial assistance.

References

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2067
https://doi.org/10.1107/S1600536812025305
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