3-Amino-2-methyl-4-oxo-3,4-dihydro­quinazolin-1-ium p-toluene­sulfonate monohydrate

Arfan, M.; Tahir, M.N.; Khan, R.; Iqbal, M.S.

doi:10.1107/S1600536809013841

3-Amino-2-methyl-4-oxo-3,4-dihydroquinazolin-1-ium p-toluenesulfonate monohydrate

M. Arfan, M. N. Tahir, R. Khan and M. S. Iqbal

In the title hydrated molecular salt, C₉H₁₀N₃O⁺·C₇H₇O₃S⁻·H₂O, the cation is protonated at a quinazolinone N atom and an intramolecular N—H

O hydrogen bond occurs. In the crystal structure, intermolecular N—H

O and O—H

O hydrogen bonds and C—H

O, C—H

π and weak aromatic π–π stacking interactions [centroid–centroid separations = 3.8648 (12) and 3.9306 (13) Å] help to establish the packing; a short S=O

π contact is also seen.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809013841/hb2950sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809013841/hb2950Isup2.hkl Contains datablock I

CCDC reference: 731282

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.091
Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGC
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGB

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.90
           From the CIF: _reflns_number_total               4390
           Count of symmetry unique reflns         2281
           Completeness (_total/calc)            192.46%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2109
           Fraction of Friedel pairs measured     0.925
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Cyclic amidines and quinazolinones, are known to possess diverse pharmacological activities as phosphodiesterase inhibitors (Glaser & Traber, 1984), anticonvulsants (Hori et al., 1990), antihypertensives (Glaser & Traber, 1984), vasodilators (Havera, 1979) and fibrinogen receptor antagonists (Liverton et al., 1998).

We now report synthesis and structure of the title compound (I), (Fig. 1), through a reaction of 2-aminobenzoic acid and hydrazine in presence of p-toluenesulfonic acid. A one pot, three component, p-toluenesulfonic acid catalyzed heterocyclization has yielded colourless prisms of (I) in the form of a p-toluenesulfonate salt with one water molecule of crystallization.

The crystal structure of (II) 3-(6-Azabicyclo(3.1.0)hex-2-en-6-yl)-2-((S)-1- hydroxy-2,2-dimethylpropyl)quinazolin-4(3H)-one (Atkinson & Meades, 2000) has been published. The title compound has also quinazoline with a chemically different attachements.

In the title compound the two fused rings A (C1—C6) and B(C1/C6/C7/N2/C8/N1) are essentially planar and the ring C (C10—C15) of the p-toluenesulfonate anion is of course planar. The title compound is stabillized due to intra- and intermolecular H-bonding as well as C–H···π and S1==O2···CgB interactions (Table 1). There also exist interactions between the centroids CgA–CgCⁱ [symmetry code: i = x, -y + 1, z + 1/2] and CgB–CgCⁱ at a distance of 3.8648 (12) and 3.9306 (13) Å, respectively. The water molecule connects the p-toluenesulfonate ions only. In the title compound there exist R₁¹(5) and R₂¹(6) ring motifs (Bernstein et al., 1995), (Fig 2).

Related literature top

For a related structure, see: Atkinson & Meades (2000). For background on the properties of cyclic amidines and quinazolinones, see: Glaser & Traber (1984); Havera (1979); Hori et al. (1990); Liverton et al. (1998). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

A mixture of anthranilic acid (0.14 g, 1 mmol), triethylorthoacetate (0.23 ml, 1.2 mmol), hydrazine hydrate (0.1 ml) and p-toluenesulfonic acid (1 g, 5 mmol) was stirred at room temperature for 1 h. After completion of the reaction as indicated by TLC, the reaction mixture was poured into water and allowed to settle, the product precipitated as colourless prisms of (I). The product was filtered, washed with water and dried. m.p. 585–594 K. yield: 72%.

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

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level. H-atoms are shown by small spheres of arbitrary radius and hydrogen bonds by dotted lines.
	Fig. 2. A fragment of the packing of (I) showing R₁¹(5) and R₂¹(6) ring motifs.

(I) top

Crystal data top

C₉H₁₀N₃O⁺·C₇H₇O₃S⁻·H₂O	F(000) = 768
M_r = 365.40	D_x = 1.404 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 4390 reflections
a = 20.838 (1) Å	θ = 2.9–28.9°
b = 6.2769 (3) Å	µ = 0.22 mm⁻¹
c = 14.7897 (7) Å	T = 296 K
β = 116.676 (1)°	Prism, colourless
V = 1728.56 (14) Å³	0.28 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4390 independent reflections
Radiation source: fine-focus sealed tube	3952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 7.30 pixels mm^-1	θ_max = 28.9°, θ_min = 2.9°
ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→6
T_min = 0.935, T_max = 0.958	l = −19→20
9546 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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0508P)² + 0.3201P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4390 reflections	Δρ_max = 0.19 e Å⁻³
243 parameters	Δρ_min = −0.22 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2109 Friedal pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)

Crystal data top

C₉H₁₀N₃O⁺·C₇H₇O₃S⁻·H₂O	V = 1728.56 (14) Å³
M_r = 365.40	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 20.838 (1) Å	µ = 0.22 mm⁻¹
b = 6.2769 (3) Å	T = 296 K
c = 14.7897 (7) Å	0.28 × 0.24 × 0.20 mm
β = 116.676 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4390 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3952 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.958	R_int = 0.022
9546 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	Δρ_max = 0.19 e Å⁻³
S = 1.00	Δρ_min = −0.22 e Å⁻³
4390 reflections	Absolute structure: Flack (1983), 2109 Friedal pairs
243 parameters	Absolute structure parameter: 0.04 (5)
2 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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
O1	0.12729 (10)	0.3093 (3)	0.49282 (14)	0.0676 (6)
N1	0.15599 (8)	0.8870 (3)	0.40550 (11)	0.0404 (4)
N2	0.19969 (9)	0.5856 (3)	0.49997 (11)	0.0442 (5)
N3	0.26093 (12)	0.4718 (4)	0.56765 (18)	0.0611 (7)
C1	0.08550 (9)	0.8146 (3)	0.36387 (13)	0.0421 (5)
C2	0.02990 (11)	0.9399 (4)	0.29579 (15)	0.0534 (6)
C3	−0.03899 (12)	0.8605 (5)	0.25562 (17)	0.0676 (8)
C4	−0.05286 (12)	0.6617 (5)	0.28300 (18)	0.0723 (9)
C5	0.00197 (13)	0.5380 (4)	0.34994 (17)	0.0607 (8)
C6	0.07242 (10)	0.6139 (3)	0.39165 (14)	0.0458 (6)
C7	0.13149 (12)	0.4861 (3)	0.46325 (15)	0.0483 (7)
C8	0.21066 (10)	0.7761 (3)	0.46961 (13)	0.0407 (5)
C9	0.28411 (11)	0.8657 (4)	0.50903 (18)	0.0573 (6)
S1	0.19585 (2)	0.35554 (7)	0.26006 (3)	0.0413 (1)
O2	0.19879 (10)	0.5841 (2)	0.27106 (14)	0.0654 (5)
O3	0.24598 (7)	0.2742 (3)	0.22604 (11)	0.0595 (5)
O4	0.20275 (8)	0.2499 (3)	0.35157 (10)	0.0551 (4)
C10	0.10901 (9)	0.2884 (3)	0.16552 (13)	0.0390 (5)
C11	0.09715 (10)	0.0902 (3)	0.12006 (14)	0.0443 (5)
C12	0.02813 (11)	0.0315 (3)	0.05242 (15)	0.0504 (6)
C13	−0.02945 (11)	0.1669 (4)	0.02991 (15)	0.0528 (6)
C14	−0.01601 (12)	0.3654 (4)	0.07515 (18)	0.0593 (7)
C15	0.05282 (11)	0.4272 (3)	0.14287 (15)	0.0497 (6)
C16	−0.10500 (13)	0.1024 (6)	−0.0422 (2)	0.0780 (9)
O5	0.30414 (16)	0.8511 (4)	0.2540 (3)	0.1157 (13)
H1	0.1621 (12)	1.020 (4)	0.3909 (17)	0.0485*
H2	0.03897	1.07432	0.27772	0.0641*
H3	−0.07674	0.94197	0.20938	0.0809*
H3A	0.2495 (16)	0.346 (5)	0.551 (2)	0.0734*
H3B	0.2630 (16)	0.493 (5)	0.626 (2)	0.0734*
H4	−0.09983	0.61162	0.25573	0.0867*
H5	−0.00766	0.40379	0.36759	0.0728*
H9A	0.31436	0.76770	0.49599	0.0688*
H9B	0.30317	0.88850	0.58061	0.0688*
H9C	0.28237	0.99873	0.47601	0.0688*
H11	0.13528	−0.00298	0.13486	0.0532*
H12	0.02028	−0.10145	0.02150	0.0605*
H14	−0.05397	0.45945	0.05983	0.0712*
H15	0.06092	0.56133	0.17269	0.0596*
H16A	−0.13244	0.08167	−0.00532	0.0934*
H16B	−0.10387	−0.02800	−0.07543	0.0934*
H16C	−0.12681	0.21226	−0.09184	0.0934*
H5A	0.284 (3)	0.949 (8)	0.248 (4)	0.1388*
H5B	0.271 (3)	0.770 (8)	0.245 (4)	0.1388*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0927 (12)	0.0463 (8)	0.0836 (11)	−0.0072 (9)	0.0571 (10)	0.0044 (8)
N1	0.0439 (7)	0.0344 (7)	0.0429 (7)	−0.0061 (6)	0.0195 (6)	−0.0032 (6)
N2	0.0556 (9)	0.0390 (8)	0.0417 (8)	0.0027 (7)	0.0252 (7)	−0.0019 (6)
N3	0.0707 (12)	0.0523 (12)	0.0608 (12)	0.0167 (10)	0.0299 (10)	0.0081 (9)
C1	0.0436 (8)	0.0496 (10)	0.0373 (8)	−0.0099 (7)	0.0218 (7)	−0.0078 (7)
C2	0.0488 (10)	0.0620 (13)	0.0474 (10)	−0.0027 (9)	0.0197 (8)	0.0049 (9)
C3	0.0440 (10)	0.103 (2)	0.0505 (11)	−0.0070 (11)	0.0166 (9)	0.0046 (12)
C4	0.0484 (11)	0.114 (2)	0.0559 (12)	−0.0311 (13)	0.0247 (10)	−0.0118 (13)
C5	0.0637 (12)	0.0704 (15)	0.0578 (12)	−0.0289 (11)	0.0361 (10)	−0.0144 (10)
C6	0.0545 (10)	0.0497 (11)	0.0427 (9)	−0.0131 (8)	0.0304 (8)	−0.0092 (8)
C7	0.0670 (13)	0.0425 (11)	0.0494 (11)	−0.0065 (9)	0.0387 (10)	−0.0048 (8)
C8	0.0475 (9)	0.0374 (9)	0.0388 (8)	−0.0016 (7)	0.0207 (7)	−0.0063 (7)
C9	0.0430 (9)	0.0518 (12)	0.0664 (12)	−0.0025 (9)	0.0150 (9)	−0.0011 (10)
S1	0.0448 (2)	0.0404 (2)	0.0389 (2)	−0.0109 (2)	0.0191 (2)	−0.0002 (2)
O2	0.0721 (9)	0.0420 (7)	0.0751 (10)	−0.0179 (8)	0.0267 (8)	−0.0047 (8)
O3	0.0470 (7)	0.0789 (11)	0.0566 (8)	−0.0051 (7)	0.0269 (7)	−0.0023 (7)
O4	0.0604 (8)	0.0616 (9)	0.0386 (6)	−0.0227 (7)	0.0180 (6)	0.0002 (6)
C10	0.0436 (8)	0.0402 (9)	0.0353 (8)	−0.0043 (7)	0.0197 (7)	0.0000 (7)
C11	0.0449 (9)	0.0429 (10)	0.0463 (9)	−0.0019 (7)	0.0215 (7)	−0.0053 (7)
C12	0.0517 (10)	0.0508 (11)	0.0472 (10)	−0.0104 (9)	0.0209 (8)	−0.0081 (8)
C13	0.0438 (9)	0.0718 (14)	0.0432 (10)	−0.0085 (9)	0.0198 (8)	0.0012 (9)
C14	0.0447 (10)	0.0708 (15)	0.0591 (13)	0.0161 (10)	0.0204 (9)	0.0053 (10)
C15	0.0572 (11)	0.0434 (10)	0.0492 (10)	0.0058 (9)	0.0246 (9)	−0.0023 (8)
C16	0.0473 (12)	0.114 (2)	0.0647 (16)	−0.0166 (13)	0.0180 (11)	−0.0023 (15)
O5	0.1089 (19)	0.0754 (15)	0.205 (3)	−0.0269 (14)	0.108 (2)	−0.0230 (18)

Geometric parameters (Å, º) top

S1—O3	1.4412 (17)	C8—C9	1.482 (3)
S1—O4	1.4551 (16)	C2—H2	0.9300
S1—O2	1.4420 (13)	C3—H3	0.9300
S1—C10	1.7707 (19)	C4—H4	0.9300
O1—C7	1.210 (3)	C5—H5	0.9300
O5—H5B	0.82 (6)	C9—H9C	0.9600
O5—H5A	0.73 (5)	C9—H9B	0.9600
N1—C1	1.390 (3)	C9—H9A	0.9600
N1—C8	1.308 (3)	C10—C11	1.383 (3)
N2—N3	1.412 (3)	C10—C15	1.375 (3)
N2—C7	1.418 (3)	C11—C12	1.383 (3)
N2—C8	1.333 (3)	C12—C13	1.384 (3)
N1—H1	0.89 (3)	C13—C14	1.382 (3)
N3—H3A	0.83 (3)	C13—C16	1.507 (4)
N3—H3B	0.86 (3)	C14—C15	1.386 (3)
C1—C6	1.390 (3)	C11—H11	0.9300
C1—C2	1.388 (3)	C12—H12	0.9300
C2—C3	1.377 (4)	C14—H14	0.9300
C3—C4	1.382 (4)	C15—H15	0.9300
C4—C5	1.369 (4)	C16—H16C	0.9600
C5—C6	1.396 (4)	C16—H16A	0.9600
C6—C7	1.453 (3)	C16—H16B	0.9600

O2—S1—C10	107.61 (11)	C2—C3—H3	119.00
O2—S1—O3	113.02 (12)	C5—C4—H4	120.00
O2—S1—O4	111.53 (11)	C3—C4—H4	120.00
O4—S1—C10	105.38 (9)	C4—C5—H5	120.00
O3—S1—O4	112.26 (10)	C6—C5—H5	120.00
O3—S1—C10	106.50 (9)	C8—C9—H9A	109.00
H5A—O5—H5B	96 (7)	C8—C9—H9B	109.00
C1—N1—C8	123.39 (18)	C8—C9—H9C	109.00
N3—N2—C7	118.69 (19)	H9A—C9—H9B	109.00
N3—N2—C8	117.1 (2)	H9A—C9—H9C	109.00
C7—N2—C8	124.06 (17)	H9B—C9—H9C	110.00
C1—N1—H1	116.1 (17)	S1—C10—C11	119.63 (15)
C8—N1—H1	120.3 (17)	S1—C10—C15	119.88 (15)
N2—N3—H3A	103 (2)	C11—C10—C15	120.33 (18)
H3A—N3—H3B	109 (3)	C10—C11—C12	119.49 (19)
N2—N3—H3B	105 (2)	C11—C12—C13	121.21 (19)
C2—C1—C6	121.2 (2)	C12—C13—C14	118.2 (2)
N1—C1—C2	120.53 (19)	C14—C13—C16	120.3 (2)
N1—C1—C6	118.30 (17)	C12—C13—C16	121.5 (2)
C1—C2—C3	118.5 (2)	C13—C14—C15	121.4 (2)
C2—C3—C4	121.0 (2)	C10—C15—C14	119.38 (19)
C3—C4—C5	120.5 (3)	C12—C11—H11	120.00
C4—C5—C6	119.8 (2)	C10—C11—H11	120.00
C5—C6—C7	120.83 (19)	C11—C12—H12	119.00
C1—C6—C7	120.12 (19)	C13—C12—H12	119.00
C1—C6—C5	119.05 (19)	C15—C14—H14	119.00
N2—C7—C6	114.30 (17)	C13—C14—H14	119.00
O1—C7—N2	119.2 (2)	C10—C15—H15	120.00
O1—C7—C6	126.5 (2)	C14—C15—H15	120.00
N2—C8—C9	120.72 (19)	C13—C16—H16B	109.00
N1—C8—N2	119.8 (2)	C13—C16—H16C	109.00
N1—C8—C9	119.51 (19)	C13—C16—H16A	109.00
C1—C2—H2	121.00	H16A—C16—H16C	109.00
C3—C2—H2	121.00	H16B—C16—H16C	109.00
C4—C3—H3	120.00	H16A—C16—H16B	109.00

O4—S1—C10—C11	−78.48 (18)	N1—C1—C6—C7	0.6 (3)
O4—S1—C10—C15	96.94 (18)	C2—C1—C6—C5	0.1 (3)
O2—S1—C10—C11	162.40 (17)	C1—C2—C3—C4	0.7 (4)
O2—S1—C10—C15	−22.2 (2)	C2—C3—C4—C5	−0.8 (4)
O3—S1—C10—C11	40.94 (19)	C3—C4—C5—C6	0.6 (4)
O3—S1—C10—C15	−143.64 (17)	C4—C5—C6—C7	179.7 (2)
C1—N1—C8—C9	179.25 (18)	C4—C5—C6—C1	−0.2 (3)
C8—N1—C1—C6	−0.1 (3)	C5—C6—C7—N2	−179.2 (2)
C1—N1—C8—N2	−1.8 (3)	C1—C6—C7—O1	−179.4 (2)
C8—N1—C1—C2	−179.68 (19)	C1—C6—C7—N2	0.7 (3)
N3—N2—C7—O1	2.0 (3)	C5—C6—C7—O1	0.7 (4)
C7—N2—C8—C9	−177.77 (19)	S1—C10—C11—C12	174.65 (16)
N3—N2—C7—C6	−178.09 (19)	C15—C10—C11—C12	−0.8 (3)
C8—N2—C7—O1	177.4 (2)	S1—C10—C15—C14	−174.44 (17)
C8—N2—C7—C6	−2.7 (3)	C11—C10—C15—C14	0.9 (3)
N3—N2—C8—N1	178.78 (19)	C10—C11—C12—C13	−0.5 (3)
N3—N2—C8—C9	−2.3 (3)	C11—C12—C13—C14	1.5 (3)
C7—N2—C8—N1	3.3 (3)	C11—C12—C13—C16	−178.8 (2)
C2—C1—C6—C7	−179.83 (19)	C12—C13—C14—C15	−1.3 (4)
N1—C1—C6—C5	−179.51 (19)	C16—C13—C14—C15	179.0 (2)
N1—C1—C2—C3	179.3 (2)	C13—C14—C15—C10	0.1 (3)
C6—C1—C2—C3	−0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.89 (3)	1.89 (3)	2.734 (3)	158 (3)
N3—H3A···O1	0.83 (3)	2.31 (4)	2.693 (3)	109 (3)
N3—H3B···O3ⁱⁱ	0.86 (3)	2.22 (3)	2.963 (3)	146 (3)
O5—H5A···O3ⁱ	0.73 (5)	2.16 (5)	2.871 (3)	166 (7)
O5—H5B···O2	0.82 (6)	2.07 (6)	2.862 (4)	162 (5)
C4—H4···O5ⁱⁱⁱ	0.93	2.58	3.423 (5)	152
C9—H9C···O4ⁱ	0.96	2.43	3.251 (3)	144
C2—H2···CgCⁱ	0.93	2.84	3.533 (2)	132
S1—O2···CgB	1.44 (1)	3.17 (1)	3.8430 (9)	107 (1)

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1, z+1/2; (iii) x−1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₃O⁺·C₇H₇O₃S⁻·H₂O
M_r	365.40
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	20.838 (1), 6.2769 (3), 14.7897 (7)
β (°)	116.676 (1)
V (Å³)	1728.56 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.935, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	9546, 4390, 3952
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.680

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.091, 1.00
No. of reflections	4390
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22
Absolute structure	Flack (1983), 2109 Friedal pairs
Absolute structure parameter	0.04 (5)

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