Doxofyllinium tetra-chloridoanti-monate(III) monohydrate.

The title compound, (C(11)H(14)N(4)O(4))[SbCl(4)]·H(2)O, comprises a protonated doxofyllinium cation [7-(1,3-dioxolan-2-ylmeth-yl)-1,3-dimethyl-2,6-dioxo-3,7-dihydro-1H-purin-9-ium], an [SbCl(4)](-) anion and a water mol-ecule linked by N-H⋯O and O-H⋯Cl hydrogen bonds: the [SbCl(4)](-) anions form centrosymmetric dimers via weak Sb⋯Cl inter-actions [Sb⋯Cl = 3.1159 (9) Å]. The geometrical arrangement in the crystal structure is characterized by slipped π-π stacking of the parallel purine ring systems, with an inter-planar separation of 3.32 Å.

Related literature

For related literature, see: Chen, Tu, Shu et al. (2007 ▶); Chen, Tu & Jin (2007 ▶);Feng et al. (2007 ▶); Franzone et al. (1981 ▶, 1989 ▶); Villani et al. (1997 ▶); Zhao & Li (2001 ▶).

Experimental

Crystal data

(C11H14N4O4)[SbCl4]·H2O

M = 548.85

Triclinic,

a = 8.9783 (5) Å

b = 10.4727 (5) Å

c = 11.0357 (4) Å

α = 68.7550 (10)°

β = 82.671 (2)°

γ = 88.228 (2)°

V = 959.10 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.03 mm−1

T = 153 (2) K

0.33 × 0.28 × 0.27 mm

Data collection

Bruker APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.459, T max = 0.486 (expected range = 0.547–0.579)

9490 measured reflections

4399 independent reflections

4151 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.05

4399 reflections

236 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.40 e Å−3

Δρmin = −2.97 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065774/gg2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065774/gg2051Isup2.hkl

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

(C11H14N4O4)[SbCl4]·H2O	Z = 2
Mr = 548.85	F000 = 540
Triclinic, P1	Dx = 1.901 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.9783 (5) Å	Cell parameters from 4733 reflections
b = 10.4727 (5) Å	θ = 2.1–26.9º
c = 11.0357 (4) Å	µ = 2.03 mm−1
α = 68.7550 (10)º	T = 153 (2) K
β = 82.671 (2)º	Block, colourless
γ = 88.228 (2)º	0.33 × 0.28 × 0.27 mm
V = 959.10 (8) Å3

Bruker APEX diffractometer	4399 independent reflections
Radiation source: fine-focus sealed tube	4151 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.046
T = 293(2) K	θmax = 27.5º
φ and ω scan	θmin = 3.1º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.459, Tmax = 0.486	k = −13→13
9490 measured reflections	l = −14→14

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.741P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4399 reflections	Δρmax = 1.40 e Å−3
236 parameters	Δρmin = −2.97 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Sb1	0.603006 (19)	0.947081 (18)	0.845084 (16)	0.01708 (9)
Cl1	0.50253 (10)	0.84549 (9)	0.69342 (9)	0.03132 (19)
Cl2	0.85111 (8)	0.95551 (8)	0.72752 (7)	0.02636 (17)
Cl3	0.70926 (9)	1.07637 (8)	0.98807 (8)	0.02720 (17)
Cl4	0.53886 (10)	1.16845 (8)	0.70074 (8)	0.02833 (18)
O3	0.7285 (2)	0.7066 (2)	0.0265 (2)	0.0210 (4)
N4	1.0810 (3)	0.6651 (3)	0.4722 (2)	0.0167 (5)
N3	1.2424 (3)	0.5255 (2)	0.3864 (2)	0.0162 (5)
C11	1.1991 (3)	0.5734 (3)	0.4877 (3)	0.0173 (5)
C8	1.0212 (3)	0.7064 (3)	0.3567 (3)	0.0153 (5)
C1	1.1882 (3)	0.5670 (3)	0.2638 (3)	0.0153 (5)
C2	1.0676 (3)	0.6614 (3)	0.2569 (3)	0.0149 (5)
O1	1.2388 (2)	0.5233 (2)	0.1794 (2)	0.0226 (5)
N1	0.9061 (3)	0.7955 (3)	0.3204 (2)	0.0182 (5)
N2	0.9814 (3)	0.7279 (3)	0.1570 (2)	0.0164 (5)
O2	1.2588 (2)	0.5340 (2)	0.5875 (2)	0.0247 (5)
C7	0.8856 (3)	0.8068 (3)	0.1984 (3)	0.0199 (6)
H7	0.8145	0.8619	0.1501	0.024*
C12	1.3671 (3)	0.4282 (3)	0.4072 (3)	0.0233 (6)
H12A	1.3891	0.4014	0.3325	0.035*
H12B	1.3390	0.3488	0.4840	0.035*
H12C	1.4544	0.4711	0.4188	0.035*
O4	0.8543 (2)	0.5081 (2)	0.1080 (2)	0.0221 (4)
C3	0.9963 (3)	0.7182 (3)	0.0266 (3)	0.0186 (6)
H3A	1.0894	0.6729	0.0131	0.022*
H3B	1.0012	0.8097	−0.0395	0.022*
C4	0.8666 (3)	0.6396 (3)	0.0103 (3)	0.0170 (5)
H4	0.8816	0.6326	−0.0766	0.020*
C5	0.6971 (4)	0.4720 (3)	0.1295 (3)	0.0254 (6)
H5A	0.6695	0.4048	0.2166	0.030*
H5B	0.6713	0.4361	0.0652	0.030*
C6	0.6219 (4)	0.6067 (4)	0.1140 (4)	0.0362 (8)
H6A	0.5284	0.6123	0.0770	0.043*
H6B	0.6014	0.6188	0.1975	0.043*
C10	1.0375 (4)	0.7258 (3)	0.5723 (3)	0.0230 (6)
H10A	1.0918	0.6828	0.6458	0.035*
H10B	0.9316	0.7121	0.6004	0.035*
H10C	1.0607	0.8222	0.5359	0.035*
O5	0.7621 (3)	0.9581 (3)	0.4328 (2)	0.0308 (5)
H1	0.857 (4)	0.845 (4)	0.367 (4)	0.024 (9)*
H5C	0.731 (4)	0.907 (3)	0.5067 (18)	0.029*
H5D	0.699 (3)	1.004 (3)	0.390 (3)	0.029*

	U11	U22	U33	U12	U13	U23
Sb1	0.01524 (12)	0.01761 (13)	0.01647 (12)	0.00463 (8)	−0.00456 (8)	−0.00337 (9)
Cl1	0.0308 (4)	0.0267 (4)	0.0434 (5)	0.0035 (3)	−0.0099 (3)	−0.0195 (4)
Cl2	0.0185 (3)	0.0339 (4)	0.0231 (3)	0.0024 (3)	−0.0001 (3)	−0.0070 (3)
Cl3	0.0209 (4)	0.0285 (4)	0.0289 (4)	−0.0004 (3)	−0.0088 (3)	−0.0045 (3)
Cl4	0.0357 (4)	0.0188 (4)	0.0285 (4)	0.0071 (3)	−0.0144 (3)	−0.0031 (3)
O3	0.0136 (9)	0.0262 (11)	0.0211 (10)	0.0040 (8)	−0.0060 (8)	−0.0051 (9)
N4	0.0172 (11)	0.0215 (12)	0.0123 (10)	0.0048 (9)	−0.0057 (9)	−0.0063 (9)
N3	0.0149 (11)	0.0191 (12)	0.0146 (10)	0.0056 (9)	−0.0061 (9)	−0.0052 (9)
C11	0.0158 (12)	0.0212 (14)	0.0148 (12)	0.0024 (10)	−0.0044 (10)	−0.0057 (11)
C8	0.0141 (12)	0.0180 (13)	0.0141 (12)	0.0029 (10)	−0.0055 (10)	−0.0050 (10)
C1	0.0124 (12)	0.0190 (13)	0.0140 (12)	−0.0004 (10)	−0.0038 (10)	−0.0048 (11)
C2	0.0133 (12)	0.0200 (13)	0.0115 (11)	0.0023 (10)	−0.0060 (9)	−0.0042 (10)
O1	0.0219 (11)	0.0312 (12)	0.0189 (10)	0.0091 (9)	−0.0056 (8)	−0.0139 (9)
N1	0.0171 (11)	0.0205 (12)	0.0188 (11)	0.0067 (9)	−0.0069 (9)	−0.0082 (10)
N2	0.0151 (11)	0.0206 (12)	0.0137 (10)	0.0026 (9)	−0.0075 (9)	−0.0047 (9)
O2	0.0234 (11)	0.0353 (13)	0.0155 (9)	0.0084 (9)	−0.0107 (8)	−0.0070 (9)
C7	0.0168 (13)	0.0237 (15)	0.0215 (13)	0.0053 (11)	−0.0084 (11)	−0.0093 (12)
C12	0.0209 (14)	0.0281 (16)	0.0201 (13)	0.0135 (12)	−0.0081 (11)	−0.0068 (12)
O4	0.0227 (11)	0.0215 (11)	0.0203 (10)	0.0024 (8)	−0.0035 (8)	−0.0052 (9)
C3	0.0171 (13)	0.0276 (15)	0.0117 (12)	0.0020 (11)	−0.0046 (10)	−0.0071 (11)
C4	0.0154 (13)	0.0218 (14)	0.0149 (12)	0.0049 (11)	−0.0056 (10)	−0.0071 (11)
C5	0.0277 (16)	0.0304 (17)	0.0179 (13)	−0.0070 (13)	0.0006 (12)	−0.0091 (13)
C6	0.0223 (16)	0.037 (2)	0.0401 (19)	−0.0003 (14)	−0.0018 (14)	−0.0035 (16)
C10	0.0269 (15)	0.0301 (17)	0.0159 (13)	0.0065 (12)	−0.0065 (11)	−0.0122 (12)
O5	0.0291 (12)	0.0417 (15)	0.0262 (11)	0.0164 (11)	−0.0078 (9)	−0.0176 (11)

Sb1—Cl4	2.3915 (7)	N2—C3	1.468 (3)
Sb1—Cl2	2.4176 (7)	C7—H7	0.9300
Sb1—Cl1	2.5460 (9)	C12—H12A	0.9600
Sb1—Cl3	2.6917 (9)	C12—H12B	0.9600
O3—C6	1.428 (4)	C12—H12C	0.9600
O3—C4	1.429 (3)	O4—C4	1.405 (3)
N4—C8	1.364 (3)	O4—C5	1.440 (4)
N4—C11	1.392 (3)	C3—C4	1.512 (4)
N4—C10	1.470 (4)	C3—H3A	0.9700
N3—C11	1.392 (4)	C3—H3B	0.9700
N3—C1	1.409 (3)	C4—H4	0.9800
N3—C12	1.473 (3)	C5—C6	1.507 (5)
C11—O2	1.216 (4)	C5—H5A	0.9700
C8—C2	1.362 (4)	C5—H5B	0.9700
C8—N1	1.369 (3)	C6—H6A	0.9700
C1—O1	1.213 (3)	C6—H6B	0.9700
C1—C2	1.434 (4)	C10—H10A	0.9600
C2—N2	1.388 (3)	C10—H10B	0.9600
N1—C7	1.344 (4)	C10—H10C	0.9600
N1—H1	0.92 (4)	O5—H5C	0.81 (3)
N2—C7	1.327 (4)	O5—H5D	0.81 (3)
Cl4—Sb1—Cl2	93.49 (3)	H12A—C12—H12B	109.5
Cl4—Sb1—Cl1	88.23 (3)	N3—C12—H12C	109.5
Cl2—Sb1—Cl1	88.95 (3)	H12A—C12—H12C	109.5
Cl4—Sb1—Cl3	86.84 (3)	H12B—C12—H12C	109.5
Cl2—Sb1—Cl3	90.02 (3)	C4—O4—C5	105.2 (2)
Cl1—Sb1—Cl3	174.90 (3)	N2—C3—C4	112.1 (2)
C6—O3—C4	108.5 (2)	N2—C3—H3A	109.2
C8—N4—C11	117.8 (2)	C4—C3—H3A	109.2
C8—N4—C10	122.3 (2)	N2—C3—H3B	109.2
C11—N4—C10	119.4 (2)	C4—C3—H3B	109.2
C11—N3—C1	127.4 (2)	H3A—C3—H3B	107.9
C11—N3—C12	115.5 (2)	O4—C4—O3	106.6 (2)
C1—N3—C12	116.9 (2)	O4—C4—C3	110.1 (2)
O2—C11—N3	121.5 (3)	O3—C4—C3	110.1 (2)
O2—C11—N4	121.2 (3)	O4—C4—H4	110.0
N3—C11—N4	117.3 (2)	O3—C4—H4	110.0
C2—C8—N4	124.1 (2)	C3—C4—H4	110.0
C2—C8—N1	108.2 (2)	O4—C5—C6	102.8 (3)
N4—C8—N1	127.7 (2)	O4—C5—H5A	111.2
O1—C1—N3	122.2 (2)	C6—C5—H5A	111.2
O1—C1—C2	126.7 (3)	O4—C5—H5B	111.2
N3—C1—C2	111.1 (2)	C6—C5—H5B	111.2
C8—C2—N2	106.7 (2)	H5A—C5—H5B	109.1
C8—C2—C1	122.1 (2)	O3—C6—C5	103.9 (3)
N2—C2—C1	131.2 (2)	O3—C6—H6A	111.0
C7—N1—C8	107.2 (2)	C5—C6—H6A	111.0
C7—N1—H1	125 (2)	O3—C6—H6B	111.0
C8—N1—H1	127 (2)	C5—C6—H6B	111.0
C7—N2—C2	107.7 (2)	H6A—C6—H6B	109.0
C7—N2—C3	125.6 (2)	N4—C10—H10A	109.5
C2—N2—C3	126.7 (2)	N4—C10—H10B	109.5
N2—C7—N1	110.1 (2)	H10A—C10—H10B	109.5
N2—C7—H7	125.0	N4—C10—H10C	109.5
N1—C7—H7	125.0	H10A—C10—H10C	109.5
N3—C12—H12A	109.5	H10B—C10—H10C	109.5
N3—C12—H12B	109.5	H5C—O5—H5D	116.0 (19)
C1—N3—C11—O2	−176.7 (3)	O1—C1—C2—N2	−1.4 (5)
C12—N3—C11—O2	−1.7 (4)	N3—C1—C2—N2	−180.0 (3)
C1—N3—C11—N4	5.3 (4)	C2—C8—N1—C7	−1.4 (3)
C12—N3—C11—N4	−179.7 (3)	N4—C8—N1—C7	179.5 (3)
C8—N4—C11—O2	179.0 (3)	C8—C2—N2—C7	−1.3 (3)
C10—N4—C11—O2	6.1 (4)	C1—C2—N2—C7	−178.8 (3)
C8—N4—C11—N3	−3.1 (4)	C8—C2—N2—C3	176.4 (3)
C10—N4—C11—N3	−175.9 (3)	C1—C2—N2—C3	−1.1 (5)
C11—N4—C8—C2	1.4 (4)	C2—N2—C7—N1	0.5 (3)
C10—N4—C8—C2	174.1 (3)	C3—N2—C7—N1	−177.3 (3)
C11—N4—C8—N1	−179.7 (3)	C8—N1—C7—N2	0.6 (3)
C10—N4—C8—N1	−7.0 (5)	C7—N2—C3—C4	−73.4 (4)
C11—N3—C1—O1	176.4 (3)	C2—N2—C3—C4	109.3 (3)
C12—N3—C1—O1	1.4 (4)	C5—O4—C4—O3	31.0 (3)
C11—N3—C1—C2	−5.0 (4)	C5—O4—C4—C3	150.4 (2)
C12—N3—C1—C2	−180.0 (3)	C6—O3—C4—O4	−12.6 (3)
N4—C8—C2—N2	−179.2 (3)	C6—O3—C4—C3	−132.0 (3)
N1—C8—C2—N2	1.7 (3)	N2—C3—C4—O4	−56.9 (3)
N4—C8—C2—C1	−1.4 (5)	N2—C3—C4—O3	60.4 (3)
N1—C8—C2—C1	179.5 (3)	C4—O4—C5—C6	−36.3 (3)
O1—C1—C2—C8	−178.6 (3)	C4—O3—C6—C5	−9.9 (4)
N3—C1—C2—C8	2.9 (4)	O4—C5—C6—O3	28.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.92 (4)	1.75 (4)	2.663 (4)	172 (4)
O5—H5C···Cl1	0.81 (3)	2.65 (2)	3.332 (3)	142 (2)
O5—H5D···Cl1i	0.81 (3)	2.41 (2)	3.205 (3)	166 (5)
C3—H3A···O1	0.97	2.45	3.145 (8)	128
C7—H7···Cl3ii	0.93	2.56	3.432 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.92 (4)	1.75 (4)	2.663 (4)	172 (4)
O5—H5C⋯Cl1	0.81 (3)	2.65 (2)	3.332 (3)	142 (2)
O5—H5D⋯Cl1i	0.81 (3)	2.41 (2)	3.205 (3)	166 (5)
C3—H3A⋯O1	0.97	2.45	3.145 (8)	128
C7—H7⋯Cl3ii	0.93	2.56	3.432 (3)	157

Symmetry codes: (i) ; (ii) .