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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 66| Part 8| August 2010| Page o1929
https://doi.org/10.1107/S1600536810025547

2-Amino-1,3-benzo­thia­zol-3-ium di­hydrogen phosphate

Sabahat Zahra Siddiqui,a Usama Waqas,a Mehmet Akkurt,b* Aziz-ur-Rehmana and Islam Ullah Khana

aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 27 June 2010; accepted 29 June 2010; online 7 July 2010)

The cation of the title compound, C7H7N2S+·H2PO4−, is almost planar (r.m.s deviation = 0.017 Å for all non-H atoms). In the crystal structure, the cations and anions are connected by N—H⋯O and O—H⋯O hydrogen bonds, with π–π stacking inter­actions between neighbouring 1,3-thia­zole and benzene rings [centroid–centroid distance = 3.5711 (11) Å], forming a three-dimensional network.

Related literature

For the structural parameters of some organic dihydrogeno­monophosphates, see: Gholivand et al. (2007[Gholivand, K., Zare, K., Afshar, F., Shariatinia, Z. & Khavasi, H. R. (2007). Acta Cryst. E63, o4027.]); Mrad et al. (2009[Mrad, M. L., Akriche, S., Rzaigui, M. & Ben Nasr, C. (2009). Acta Cryst. E65, o757-o758.]). For the biological and pharmacological properties of heterocyclic compounds, see: Malik et al. (2010[Malik, J. K., Manvi, F. V., Nanjwede, B. K., Singh, S. & Purohit, P. (2010). Pharm. Lett. 2, 347-359.]); Sinha & Tiwari (1986[Sinha, A. I. P. & Tiwari, S. P. (1986). Curr. Sci. 55, 386-390.]). For the synthesis, see: Thomas et al. (2003[Thomas, L., Gupta, A. & Gupta, V. (2003). J. Fluorine Chem. 22, 207-213.]).

[Scheme 1]

Experimental

Crystal data

  • C7H7N2S+·H2PO4−

  • Mr = 248.20

  • Monoclinic, P 21 /c

  • a = 12.3915 (4) Å

  • b = 10.1572 (3) Å

  • c = 8.3159 (2) Å

  • β = 103.775 (1)°

  • V = 1016.56 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.47 mm−1

  • T = 296 K

  • 0.25 × 0.09 × 0.07 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • 9333 measured reflections

  • 2490 independent reflections

  • 1938 reflections with I > 2σ(I)

  • Rint = 0.033
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.096

  • S = 1.03

  • 2490 reflections

  • 151 parameters

  • 5 restraints

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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.873 (16) 1.800 (16) 2.6693 (18) 174 (3)
N2—H6⋯O3ii 0.86 (2) 2.39 (2) 3.138 (2) 147 (2)
N2—H6⋯O4ii 0.86 (2) 2.31 (2) 3.076 (2) 149.3 (19)
N2—H7⋯O3i 0.862 (18) 2.018 (18) 2.875 (2) 172 (2)
O1—H8⋯O2iii 0.809 (19) 1.795 (19) 2.6017 (18) 175 (3)
O4—H9⋯O3iv 0.801 (17) 1.765 (17) 2.5654 (18) 178 (3)
Symmetry codes: (i) x, y-1, z+1; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y+{\script{3\over 2}}, z-{\script{1\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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) 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/S1600536810025547/bt5282sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025547/bt5282Isup2.hkl

checkCIF report


Comment top

In recent years analogues and derivatives of heterocyclic compounds have attracted strong interest due to their useful biological and pharmacological properties. The substituted benzothiazole derivatives have been reported to possess good antibacterial and antifungal activities. Several of its metal complexes have also displayed potent anti-neoplastic, anti-viral and anti-tumour activities (Malik et al., 2010; Sinha & Tiwari, 1986). In the present paper, the structure of 2-amino-1,3-benzothiazol-3-ium dihydrogen phosphate has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the cation of the title compound (I), (Fig. 1), the 1,3-benzothiazol-3-ium ring system (S1/N1/C1–C7) is almost planar (r.m.s deviation = 0.002 Å). In the anion, the bond lengths are P1—O1 = 1.5531 (16), P1—O4 = 1.5638 (17), P1—O2 = 1.5017 (12) and P1—O3 = 1.5024 (14) Å. These values are in full agreement with those found in such anions in other organic dihydrogenomonophosphates [Gholivand et al., 2007; Mrad et al., 2009]. The phosphorus atom has a slightly distorted tetrahedral coordination.

In the crystal structure, the cation and anion components are connected by intermolecular N—H···O and O—H···O hydrogen bonds (Table 1, Fig. 2), with π-π stacking interactions between neighbouring 1,3-thiazole and benzene rings [Cg1···Cg2v= 3.5711 (11) Å; symmetry code: (v) x, 1/2 - y, 1/2 + z; Cg1 and Cg2 are the centroids of the S1/N1/C1/C6/C7 1,3-thiazole and C1–C6 benzene rings, repectively], forming a three-dimensional supramolecular network.

Related literature top

For the structural parameters of some organic dihydrogenomonophosphates, see: Gholivand et al. (2007); Mrad et al. (2009). For the biological and pharmacological properties of heterocyclic compounds, see: Malik et al. (2010); Sinha & Tiwari (1986). For the synthesis, see: Thomas et al. (2003).

Experimental top

The title compound was synthesized using the method of Thomas et al. (2003), but with few modifications as follows. 0.1 mole of aniline and 9 ml of concentrated hydrochloric acid were taken in a round bottom flask equipped with reflux condenser, as the insoluble white precipitates of aniline hydrochloride were formed, 25 ml of distilled water was added and the reactants were heated for 35 min. After cooling at room temperature 0.1 moles of sodium thiocyanate were added and the mixture was further refluxed and stirred for 5 h. The resulting mixture was then cooled at room temperature and off-white crystalline solid of phenylthiourea separated out.

0.07 moles of phenyl thiourea were dissolved in 70 ml chloroform in a three-necked round bottom flask equipped with reflux condenser, the whole apparatus was fitted in an ice bath. 0.07 M of bromine in 70 ml of chloroform was added drop wise in a period of 2 h in the reaction mixture. The temperature was maintained at 277 K. After the addition of bromine, the mixture was stirred at room temperature for 4 h and was further refluxed for about 3 h until the evolution of hydrogen bromide stopped. On moderate cooling solid separated out filtered and washed with sulfur dioxide water (10 ml conc. H2SO4 in 50 ml water). The filtrate was neutralized with aqueous ammonia (25%). Precipitates of 2-aminobenzothiazole separated out. Filtered and washed thoroughly with water and re-crystallized in ethanol.

Then 0.001 moles of 2-aminobenzothiazole in 3 ml of methanol and 1–2 drops of o-phosphoric acid were added in a round bottom flask. The reaction mixture was refluxed for 8–10 h with continuous stirring. On gradual cooling crystalline solid separated out. Filtered and washed the solid with water and recrystallized in methanol to yield the final product.

Refinement top

Hydroxyl H atoms and H atoms on N atoms were located in a difference Fourier map and refined as riding in their as-found relative positions, with Uiso(H) = 1.5Ueq(O) and Uiso(H) = 1.2Ueq(N). The distances O—H and N—H were restrained to 0.83 and 0.86 Å, respectively. H atoms bonded to C atoms were positioned geometrically and refined using a riding model, [C—–H = 0.93 Å and Uiso(H) = 1.2Ueq(C)].

Structure description top

In recent years analogues and derivatives of heterocyclic compounds have attracted strong interest due to their useful biological and pharmacological properties. The substituted benzothiazole derivatives have been reported to possess good antibacterial and antifungal activities. Several of its metal complexes have also displayed potent anti-neoplastic, anti-viral and anti-tumour activities (Malik et al., 2010; Sinha & Tiwari, 1986). In the present paper, the structure of 2-amino-1,3-benzothiazol-3-ium dihydrogen phosphate has been determined as part of a research program involving the synthesis and biological evaluation of sulfur containing compounds.

In the cation of the title compound (I), (Fig. 1), the 1,3-benzothiazol-3-ium ring system (S1/N1/C1–C7) is almost planar (r.m.s deviation = 0.002 Å). In the anion, the bond lengths are P1—O1 = 1.5531 (16), P1—O4 = 1.5638 (17), P1—O2 = 1.5017 (12) and P1—O3 = 1.5024 (14) Å. These values are in full agreement with those found in such anions in other organic dihydrogenomonophosphates [Gholivand et al., 2007; Mrad et al., 2009]. The phosphorus atom has a slightly distorted tetrahedral coordination.

In the crystal structure, the cation and anion components are connected by intermolecular N—H···O and O—H···O hydrogen bonds (Table 1, Fig. 2), with π-π stacking interactions between neighbouring 1,3-thiazole and benzene rings [Cg1···Cg2v= 3.5711 (11) Å; symmetry code: (v) x, 1/2 - y, 1/2 + z; Cg1 and Cg2 are the centroids of the S1/N1/C1/C6/C7 1,3-thiazole and C1–C6 benzene rings, repectively], forming a three-dimensional supramolecular network.

For the structural parameters of some organic dihydrogenomonophosphates, see: Gholivand et al. (2007); Mrad et al. (2009). For the biological and pharmacological properties of heterocyclic compounds, see: Malik et al. (2010); Sinha & Tiwari (1986). For the synthesis, see: Thomas et al. (2003).

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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the title molecule. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram viewed down the c axis. Only H atoms involved in hydrogen bonding are shown.
2-Amino-1,3-benzothiazol-3-ium dihydrogen phosphate top
Crystal data top
C7H7N2S+·H2PO4−F(000) = 512
Mr = 248.20Dx = 1.622 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2983 reflections
a = 12.3915 (4) Åθ = 2.6–27.1°
b = 10.1572 (3) ŵ = 0.47 mm−1
c = 8.3159 (2) ÅT = 296 K
β = 103.775 (1)°Rod, off-white
V = 1016.56 (5) Å30.25 × 0.09 × 0.07 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		1938 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.033
Graphite monochromatorθmax = 28.3°, θmin = 3.2°
φ and ω scansh = −13→16
9333 measured reflectionsk = −8→13
2490 independent reflectionsl = −11→8
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1064P]
where P = (Fo2 + 2Fc2)/3
2490 reflections(Δ/σ)max = 0.001
151 parametersΔρmax = 0.31 e Å−3
5 restraintsΔρmin = −0.26 e Å−3
Crystal data top
C7H7N2S+·H2PO4−V = 1016.56 (5) Å3
Mr = 248.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.3915 (4) ŵ = 0.47 mm−1
b = 10.1572 (3) ÅT = 296 K
c = 8.3159 (2) Å0.25 × 0.09 × 0.07 mm
β = 103.775 (1)°
Data collection top
Bruker APEXII CCD
diffractometer		1938 reflections with I > 2σ(I)
9333 measured reflectionsRint = 0.033
2490 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0385 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.31 e Å−3
2490 reflectionsΔρmin = −0.26 e Å−3
151 parameters
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 e.s.d.'s 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
xyzUiso*/Ueq
S10.35481 (4)0.35955 (5)1.06135 (6)0.0400 (2)
N10.28028 (14)0.13298 (14)0.95775 (19)0.0362 (5)
N20.43880 (16)0.12254 (17)1.1731 (2)0.0460 (6)
C10.23286 (16)0.35055 (18)0.9039 (2)0.0363 (6)
C20.16650 (19)0.4518 (2)0.8240 (3)0.0494 (7)
C30.07398 (19)0.4193 (2)0.7023 (3)0.0555 (8)
C40.04759 (19)0.2898 (2)0.6589 (3)0.0525 (7)
C50.11376 (17)0.1882 (2)0.7386 (2)0.0436 (6)
C60.20561 (15)0.22026 (17)0.8625 (2)0.0340 (6)
C70.36161 (16)0.18903 (19)1.0689 (2)0.0350 (5)
P10.31052 (4)0.78446 (4)0.06814 (5)0.0321 (2)
O10.21014 (12)0.72357 (14)0.12333 (17)0.0448 (5)
O20.26558 (12)0.87196 (11)−0.07803 (14)0.0396 (4)
O30.38850 (12)0.84982 (13)0.21213 (15)0.0441 (4)
O40.37402 (14)0.66563 (15)0.01419 (16)0.0497 (5)
H10.271 (2)0.0479 (16)0.948 (3)0.0600*
H20.183900.539300.851700.0590*
H30.028100.486000.647900.0670*
H4−0.015100.270700.575600.0630*
H50.096800.100900.709500.0520*
H60.4904 (18)0.164 (2)1.242 (3)0.0600*
H70.430 (2)0.0391 (17)1.184 (3)0.0600*
H80.228 (2)0.690 (3)0.214 (2)0.0750*
H90.379 (2)0.663 (3)−0.080 (2)0.0750*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0424 (3)0.0331 (3)0.0412 (3)−0.0075 (2)0.0035 (2)−0.0034 (2)
N10.0421 (9)0.0296 (8)0.0326 (8)−0.0059 (7)0.0007 (7)0.0004 (6)
N20.0446 (10)0.0425 (9)0.0417 (10)−0.0074 (8)−0.0079 (8)0.0031 (8)
C10.0357 (10)0.0384 (10)0.0352 (9)−0.0013 (8)0.0092 (8)−0.0010 (8)
C20.0530 (13)0.0418 (11)0.0525 (12)0.0090 (10)0.0110 (10)0.0023 (10)
C30.0512 (13)0.0605 (14)0.0515 (13)0.0172 (11)0.0055 (10)0.0062 (11)
C40.0370 (11)0.0749 (16)0.0409 (11)0.0027 (11)0.0000 (9)0.0000 (10)
C50.0400 (11)0.0500 (11)0.0383 (10)−0.0081 (9)0.0043 (8)−0.0034 (9)
C60.0347 (10)0.0382 (10)0.0290 (9)−0.0026 (8)0.0074 (7)0.0013 (7)
C70.0371 (10)0.0350 (9)0.0321 (9)−0.0055 (8)0.0068 (8)0.0006 (7)
P10.0371 (3)0.0314 (3)0.0236 (2)0.0020 (2)−0.0009 (2)0.0029 (2)
O10.0399 (8)0.0585 (9)0.0308 (7)−0.0073 (7)−0.0021 (6)0.0036 (6)
O20.0562 (9)0.0307 (6)0.0256 (6)0.0059 (6)−0.0027 (6)0.0010 (5)
O30.0462 (8)0.0503 (8)0.0292 (7)−0.0127 (6)−0.0038 (6)0.0042 (6)
O40.0685 (10)0.0476 (8)0.0334 (7)0.0263 (7)0.0128 (7)0.0122 (7)
Geometric parameters (Å, º) top
S1—C11.7504 (19)N2—H70.862 (18)
S1—C71.735 (2)N2—H60.86 (2)
P1—O31.5024 (14)C1—C61.389 (3)
P1—O11.5531 (16)C1—C21.384 (3)
P1—O21.5017 (12)C2—C31.377 (3)
P1—O41.5638 (17)C3—C41.382 (3)
O1—H80.809 (19)C4—C51.385 (3)
O4—H90.801 (17)C5—C61.380 (3)
N1—C61.386 (2)C2—H20.9300
N1—C71.323 (2)C3—H30.9300
N2—C71.314 (3)C4—H40.9300
N1—H10.873 (16)C5—H50.9300
S1···O4i3.1497 (16)C1···C7xi3.547 (3)
S1···N12.5519 (16)C1···C5iii3.469 (3)
S1···O3ii3.2897 (15)C4···C6xi3.496 (3)
S1···C5iii3.664 (2)C5···S1xi3.664 (2)
S1···C6iii3.5429 (18)C5···C1xi3.469 (3)
P1···O2iv3.5032 (13)C6···C4iii3.496 (3)
P1···H6v2.87 (2)C6···C7xi3.577 (3)
P1···H8vi2.890 (16)C6···S1xi3.5429 (18)
P1···H9iv2.896 (17)C7···C6iii3.577 (3)
P1···H1vii2.857 (17)C7···C1iii3.547 (3)
P1···H7vii3.02 (2)C3···H3xii3.0400
O1···O2iv2.6017 (18)C3···H5xiii3.0300
O2···N1vii2.6693 (18)C5···H3xiv3.0000
O2···P1vi3.5032 (13)H1···P1x2.857 (17)
O2···O1vi2.6017 (18)H1···O2x1.800 (16)
O3···N2vii2.875 (2)H1···H72.43 (3)
O3···S1v3.2897 (15)H2···O4i2.7400
O3···N2v3.138 (2)H2···O1i2.8900
O3···O4iv2.5654 (18)H3···C5xiii3.0000
O4···S1viii3.1497 (16)H3···H3xii2.4100
O4···O3vi2.5654 (18)H3···H5xiii2.4600
O4···N2v3.076 (2)H3···C3xii3.0400
O1···H4ix2.6300H4···O1xv2.6300
O1···H2viii2.8900H5···H3xiv2.4600
O2···H8vi1.795 (18)H5···C3xiv3.0300
O2···H1vii1.799 (16)H6···O4ii2.31 (2)
O3···H7vii2.018 (18)H6···O3ii2.39 (2)
O3···H9iv1.765 (17)H6···P1ii2.87 (2)
O3···H6v2.39 (2)H7···O3x2.018 (18)
O4···H6v2.31 (2)H7···H12.43 (3)
O4···H2viii2.7400H7···P1x3.02 (2)
N1···O2x2.6693 (18)H8···P1iv2.890 (16)
N1···S12.5519 (16)H8···O2iv1.795 (19)
N2···O3ii3.138 (2)H9···P1vi2.896 (17)
N2···O4ii3.076 (2)H9···O3vi1.765 (17)
N2···O3x2.875 (2)
C1—S1—C790.04 (9)C1—C2—C3118.06 (19)
O2—P1—O4109.85 (7)C2—C3—C4121.6 (2)
O3—P1—O4107.32 (8)C3—C4—C5120.5 (2)
O1—P1—O2107.83 (8)C4—C5—C6118.07 (19)
O1—P1—O3110.41 (8)C1—C6—C5121.24 (17)
O1—P1—O4105.70 (8)N1—C6—C1112.22 (15)
O2—P1—O3115.33 (7)N1—C6—C5126.55 (17)
P1—O1—H8112.5 (18)N1—C7—N2123.59 (18)
P1—O4—H9118 (2)S1—C7—N1112.46 (13)
C6—N1—C7114.70 (15)S1—C7—N2123.95 (15)
C7—N1—H1123.5 (16)C3—C2—H2121.00
C6—N1—H1121.7 (16)C1—C2—H2121.00
H6—N2—H7120 (2)C4—C3—H3119.00
C7—N2—H6119.8 (14)C2—C3—H3119.00
C7—N2—H7119.0 (17)C3—C4—H4120.00
C2—C1—C6120.50 (18)C5—C4—H4120.00
S1—C1—C6110.54 (13)C4—C5—H5121.00
S1—C1—C2128.96 (15)C6—C5—H5121.00
C7—S1—C1—C2178.1 (2)S1—C1—C2—C3179.72 (17)
C7—S1—C1—C6−1.63 (15)C6—C1—C2—C3−0.5 (3)
C1—S1—C7—N2−178.14 (18)C2—C1—C6—N1−178.75 (18)
C1—S1—C7—N11.89 (15)C2—C1—C6—C51.6 (3)
C6—N1—C7—N2178.35 (18)C1—C2—C3—C4−0.5 (4)
C7—N1—C6—C5−179.97 (19)C2—C3—C4—C50.6 (4)
C7—N1—C6—C10.4 (2)C3—C4—C5—C60.5 (3)
C6—N1—C7—S1−1.7 (2)C4—C5—C6—C1−1.5 (3)
S1—C1—C6—N11.0 (2)C4—C5—C6—N1178.86 (19)
S1—C1—C6—C5−178.61 (15)
Symmetry codes: (i) x, y, z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) x, −y+3/2, z+1/2; (v) −x+1, y+1/2, −z+3/2; (vi) x, −y+3/2, z−1/2; (vii) x, y+1, z−1; (viii) x, y, z−1; (ix) −x, y+1/2, −z+1/2; (x) x, y−1, z+1; (xi) x, −y+1/2, z−1/2; (xii) −x, −y+1, −z+1; (xiii) −x, y+1/2, −z+3/2; (xiv) −x, y−1/2, −z+3/2; (xv) −x, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2x0.873 (16)1.800 (16)2.6693 (18)174 (3)
N2—H6···O3ii0.86 (2)2.39 (2)3.138 (2)147 (2)
N2—H6···O4ii0.86 (2)2.31 (2)3.076 (2)149.3 (19)
N2—H7···O3x0.862 (18)2.018 (18)2.875 (2)172 (2)
O1—H8···O2iv0.809 (19)1.795 (19)2.6017 (18)175 (3)
O4—H9···O3vi0.801 (17)1.765 (17)2.5654 (18)178 (3)
Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iv) x, −y+3/2, z+1/2; (vi) x, −y+3/2, z−1/2; (x) x, y−1, z+1.

Experimental details

Crystal data
Chemical formulaC7H7N2S+·H2PO4−
Mr248.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)12.3915 (4), 10.1572 (3), 8.3159 (2)
β (°) 103.775 (1)
V (Å3)1016.56 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.47
Crystal size (mm)0.25 × 0.09 × 0.07
Data collection
DiffractometerBruker APEXII CCD
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		9333, 2490, 1938
Rint0.033
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.096, 1.03
No. of reflections2490
No. of parameters151
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.31, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.873 (16)1.800 (16)2.6693 (18)174 (3)
N2—H6···O3ii0.86 (2)2.39 (2)3.138 (2)147 (2)
N2—H6···O4ii0.86 (2)2.31 (2)3.076 (2)149.3 (19)
N2—H7···O3i0.862 (18)2.018 (18)2.875 (2)172 (2)
O1—H8···O2iii0.809 (19)1.795 (19)2.6017 (18)175 (3)
O4—H9···O3iv0.801 (17)1.765 (17)2.5654 (18)178 (3)
Symmetry codes: (i) x, y−1, z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2.
 

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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 First citationMalik, J. K., Manvi, F. V., Nanjwede, B. K., Singh, S. & Purohit, P. (2010). Pharm. Lett. 2, 347–359.  CAS Google Scholar
 First citationMrad, M. L., Akriche, S., Rzaigui, M. & Ben Nasr, C. (2009). Acta Cryst. E65, o757–o758.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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 First citationSinha, A. I. P. & Tiwari, S. P. (1986). Curr. Sci. 55, 386–390.  CAS Google Scholar
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 First citationThomas, L., Gupta, A. & Gupta, V. (2003). J. Fluorine Chem. 22, 207–213.  Web of Science CrossRef Google Scholar

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1929
https://doi.org/10.1107/S1600536810025547
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