3-Amino-2-methyl-4-oxo-3,4-dihydro-quinazolin-1-ium p-toluene-sulfonate monohydrate.

In the title hydrated mol-ecular salt, C(9)H(10)N(3)O(+)·C(7)H(7)O(3)S(-)·H(2)O, the cation is protonated at a quinazolinone N atom and an intra-molecular N-H⋯O hydrogen bond occurs. In the crystal structure, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds and C-H⋯O, C-H⋯π and weak aromatic π-π stacking inter-actions [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.

Related literature

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

Crystal data

C9H10N3O+·C7H7O3S−·H2O

M = 365.40

Monoclinic,

a = 20.838 (1) Å

b = 6.2769 (3) Å

c = 14.7897 (7) Å

β = 116.676 (1)°

V = 1728.56 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.935, T max = 0.958

9546 measured reflections

4390 independent reflections

3952 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.091

S = 1.00

4390 reflections

243 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 2109 Friedal pairs

Flack parameter: 0.04 (5)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013841/hb2950sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013841/hb2950Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H10N3O+·C7H7O3S−·H2O	F(000) = 768
Mr = 365.40	Dx = 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

Bruker Kappa APEXII CCD diffractometer	4390 independent reflections
Radiation source: fine-focus sealed tube	3952 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 7.30 pixels mm-1	θmax = 28.9°, θmin = 2.9°
ω scans	h = −28→28
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→6
Tmin = 0.935, Tmax = 0.958	l = −19→20
9546 measured reflections

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(Fo2) + (0.0508P)2 + 0.3201P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4390 reflections	Δρmax = 0.19 e Å−3
243 parameters	Δρmin = −0.22 e Å−3
2 restraints	Absolute structure: Flack (1983), 2109 Friedal pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (5)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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	1.4420 (13)	3.169 (2)	3.8430 (9)	106.86 (10)

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) . CgB and CgC are the centroids of the C1/C6/C7/N2/C8/N1 and C10–C15 rings.