1-Phenyl­piperazine-1,4-diium bis­(hydrogen sulfate)

Marouani, H.; Rzaigui, M.; Al-Deyab, S.S.

doi:10.1107/S1600536810037001

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2613

doi:10.1107/S1600536810037001

Open

access

1-Phenylpiperazine-1,4-diium bis(hydrogen sulfate)

Houda Marouani,^a ^* Mohamed Rzaigui ^a and Salem S. Al-Deyab ^b

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bPetrochemical Research Chair, College of Science, King Saud University, Riadh, Saudi Arabia
^*Correspondence e-mail: houda.marouani@fsb.rnu.tn

(Received 9 September 2010; accepted 15 September 2010; online 25 September 2010)

In the title compound, C₁₀H₁₆N₂²⁺·2HSO₄⁻, the S atoms adopt slightly distorted tetrahedral geometry and the diprotonated piperazine ring adopts a chair conformation. In the crystal, the 1-phenylpiperazine-1,4-diium cations are anchored between chains formed by the sulfate entities via intermolecular bifurcated N—H⋯(O,O) and weak C—H⋯O hydrogen bonds. These hydrogen bonds contribute to the cohesion and stability of the network of the crystal structure.

Related literature

For pharmacological properties of phenylpiperazine, see: Cohen et al. (1982 ); Conrado et al. (2008 ); Neves et al. (2003 ). For related structures, see: Ben Gharbia et al. (2005 ). For a discussion on hydrogen bonding, see: Brown (1976 ); Blessing (1986 ). For structural discussion, see: Arbuckle et al. (2009 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₀H₁₆N₂²⁺·2HSO₄⁻
M_r = 358.38
Monoclinic, P 2₁ /c
a = 17.535 (6) Å
b = 10.996 (2) Å
c = 7.631 (2) Å
β = 99.86 (2)°
V = 1449.7 (7) Å³
Z = 4
Ag Kα radiation
λ = 0.56083 Å
μ = 0.22 mm⁻¹
T = 293 K
0.5 × 0.4 × 0.1 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
8212 measured reflections
7100 independent reflections
4535 reflections with I > 2σ(I)
R_int = 0.022
2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.127
S = 1.03
7100 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.82	1.80	2.6140 (17)	172
O5—H5⋯O7ⁱⁱ	0.82	1.80	2.6066 (18)	169
N1—H1A⋯O2ⁱⁱⁱ	0.90	2.23	2.8636 (19)	128
N1—H1A⋯O3^iv	0.90	2.30	3.0279 (19)	138
N1—H1B⋯O3	0.90	2.14	2.9251 (18)	145
N1—H1B⋯O2ⁱ	0.90	2.35	2.9892 (18)	128
N2—H2⋯O7	0.91	2.02	2.8216 (16)	146
N2—H2⋯O6ⁱⁱ	0.91	2.32	2.9037 (17)	122
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+2, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 for Windows (Farrugia, 1998 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037001/pv2328sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037001/pv2328Isup2.hkl

checkCIF report

Comment top

The phenylpiperazine and its derivatives have been intensively investigated recently owing to their interesting pharmacological, cardiovascular and autonomic properties (Conrado et al., 2008; Cohen et al., 1982; Neves et al., 2003). We report here the preparation and the crystal structure of the title compound, (I).

The asymmetric unit of the title compound (Fig.1) consists of two HSO₄^- anions and a 1-phenylpiperazine-1,4-diium cation. The interatomic bond lengths and angles of the cation show no significant deviation from those reported in other 1-phenylpiperazinium salts such as [C₁₀H₁₆N₂]₂ZnCl₄ (Ben Gharbia, et al., 2005). In the title compound, the distances S—O are significantly longer than the S═O distances as reported in the hydrogen sulfate ion previously (Arbuckle, et al., 2009). The aromatic ring is essentially planar while the diprotonated piperazine ring adopts a chair conformation, with puckering parameters (Cremer & Pople, 1975): Q = 0.5913 (14) Å, θ = 178.61 (15)° and ϕ = 76 (5)°.

The atomic arrangement is characterized by infinite chains built by HSO₄^- anions. The inorganic chains, extending along the c direction, are located around planes perpendicular to the a axis at x = 0 (for HS1O₄^-) and x = 1/4, x = 3/4 (for HS2O₄^-). The hydrogen sulfate groups of the same type are interconnected via strong O—H···O hydrogen bonds (Table 1)[d (O···O) < 2.73 Å] (Brown, 1976; Blessing, 1986). Chains formed by HS1O₄ are linked by N1 nitrogen atom of the cation to form layers parallel to the bc plane at x = 0. Two chains of different type are bound between them by the cations through their two nitrogen atoms by means of the N—H···O hydrogen bonds (Fig. 2).

The cations are linked onto the anionic chains, by forming H-bonds with the oxygen atoms with N—H···O distances in the range 2.8216 (16)–3.0279 (19) Å and C—H···O distances in the range 2.949 (2)–3.520 (2) Å. It should be noticed that all the amino hydrogen atoms are involved in bifurcated N—H···(O, O) hydrogen bonding. These hydrogen bonds contribute to the cohesion and stability of the network of the studied crystal structure.

Related literature top

For pharmacological properties of phenylpiperazine, see: Cohen et al. (1982); Conrado et al. (2008); Neves et al. (2003). For related structures, see: Ben Gharbia et al. (2005). For a discussion on hydrogen bonding, see: Brown (1976); Blessing (1986). For structural discussion, see: Arbuckle et al. (2009). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Single crystals of the title compound were prepared at room temperature from a mixture of an aqueous solution of sulfuric acid (2 mmol), 1-phenylpiperazine (1 mmol), ethanol (10 ml) and water (10 ml). The solution was stirred for 1 h then evaporated slowly at room temperature for several days until the formation of good quality of prismatic single crystals.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-32 for Windows (Farrugia, 1998); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. An ORTEP view of (I) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Projection of (I) along the c axis. H atoms non committed in H-bonds are omitted for clarity.

1-Phenylpiperazine-1,4-diium bis(hydrogen sulfate) top

Crystal data top

C₁₀H₁₆N₂²⁺·2HSO₄⁻	F(000) = 752
M_r = 358.38	D_x = 1.642 Mg m⁻³
Monoclinic, P2₁/c	Ag Kα radiation, λ = 0.56083 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 17.535 (6) Å	θ = 9–11°
b = 10.996 (2) Å	µ = 0.22 mm⁻¹
c = 7.631 (2) Å	T = 293 K
β = 99.86 (2)°	Prism, colorless
V = 1449.7 (7) Å³	0.5 × 0.4 × 0.1 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.022
Radiation source: fine-focus sealed tube	θ_max = 28.0°, θ_min = 2.4°
Graphite monochromator	h = −3→29
non–profiled ω scans	k = −18→0
8212 measured reflections	l = −12→12
7100 independent reflections	2 standard reflections every 120 min
4535 reflections with I > 2σ(I)	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0603P)² + 0.1738P] where P = (F_o² + 2F_c²)/3
7100 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₀H₁₆N₂²⁺·2HSO₄⁻	V = 1449.7 (7) Å³
M_r = 358.38	Z = 4
Monoclinic, P2₁/c	Ag Kα radiation, λ = 0.56083 Å
a = 17.535 (6) Å	µ = 0.22 mm⁻¹
b = 10.996 (2) Å	T = 293 K
c = 7.631 (2) Å	0.5 × 0.4 × 0.1 mm
β = 99.86 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.022
8212 measured reflections	2 standard reflections every 120 min
7100 independent reflections	intensity decay: 1%
4535 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
7100 reflections	Δρ_min = −0.46 e Å⁻³
201 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.958198 (19)	0.80824 (3)	0.59663 (4)	0.02129 (8)
S2	0.68841 (2)	0.18262 (3)	0.36929 (5)	0.02431 (8)
O7	0.66990 (8)	0.31003 (10)	0.32493 (15)	0.0332 (2)
O3	0.97861 (7)	0.68051 (10)	0.64169 (14)	0.0306 (2)
N2	0.73629 (7)	0.53363 (10)	0.45259 (15)	0.0215 (2)
H2	0.7163	0.4579	0.4607	0.026*
O2	0.97180 (7)	0.88315 (10)	0.75428 (14)	0.0295 (2)
N1	0.89625 (7)	0.46159 (12)	0.49684 (18)	0.0273 (2)
H1A	0.9333	0.4041	0.5136	0.033*
H1B	0.9194	0.5342	0.4913	0.033*
O1	1.01876 (7)	0.85308 (12)	0.48419 (14)	0.0355 (3)
H1	1.0036	0.8368	0.3791	0.053*
O4	0.88248 (7)	0.81856 (12)	0.49109 (16)	0.0366 (3)
O5	0.63020 (7)	0.13868 (12)	0.48817 (15)	0.0356 (3)
H5	0.6438	0.1639	0.5898	0.053*
O6	0.67139 (8)	0.10676 (11)	0.21389 (16)	0.0371 (3)
C3	0.79171 (8)	0.55729 (14)	0.62253 (19)	0.0258 (3)
H3A	0.7639	0.5567	0.7220	0.031*
H3B	0.8152	0.6368	0.6173	0.031*
C2	0.77975 (9)	0.53263 (14)	0.29912 (19)	0.0266 (3)
H2A	0.8023	0.6122	0.2876	0.032*
H2B	0.7442	0.5155	0.1900	0.032*
C5	0.67057 (8)	0.61993 (13)	0.42348 (19)	0.0244 (3)
C1	0.84293 (8)	0.43819 (14)	0.3260 (2)	0.0284 (3)
H1C	0.8203	0.3578	0.3284	0.034*
H1D	0.8716	0.4412	0.2281	0.034*
C4	0.85375 (9)	0.46091 (15)	0.6493 (2)	0.0293 (3)
H4A	0.8895	0.4765	0.7588	0.035*
H4B	0.8304	0.3817	0.6588	0.035*
O8	0.76519 (7)	0.17042 (14)	0.47005 (18)	0.0465 (3)
C10	0.68447 (10)	0.74340 (14)	0.4204 (3)	0.0346 (3)
H10	0.7348	0.7735	0.4384	0.042*
C6	0.59670 (9)	0.57280 (16)	0.3966 (2)	0.0347 (3)
H6	0.5887	0.4892	0.3987	0.042*
C9	0.62142 (12)	0.82154 (17)	0.3896 (3)	0.0468 (5)
H9	0.6293	0.9051	0.3871	0.056*
C8	0.54742 (13)	0.7761 (2)	0.3629 (3)	0.0532 (5)
H8	0.5055	0.8291	0.3422	0.064*
C7	0.53462 (10)	0.6521 (2)	0.3664 (3)	0.0489 (5)
H7	0.4843	0.6221	0.3485	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02138 (14)	0.02425 (15)	0.01794 (14)	−0.00207 (12)	0.00249 (10)	−0.00047 (11)
S2	0.02718 (16)	0.02462 (15)	0.02126 (15)	−0.00051 (13)	0.00451 (12)	0.00042 (12)
O7	0.0483 (7)	0.0228 (5)	0.0284 (5)	−0.0016 (5)	0.0067 (5)	−0.0006 (4)
O3	0.0446 (6)	0.0249 (5)	0.0219 (5)	0.0038 (5)	0.0047 (4)	0.0000 (4)
N2	0.0196 (5)	0.0189 (5)	0.0255 (5)	−0.0014 (4)	0.0029 (4)	0.0000 (4)
O2	0.0372 (6)	0.0288 (5)	0.0225 (5)	−0.0006 (4)	0.0055 (4)	−0.0059 (4)
N1	0.0198 (5)	0.0266 (6)	0.0352 (6)	−0.0001 (4)	0.0037 (5)	0.0005 (5)
O1	0.0341 (6)	0.0512 (7)	0.0225 (5)	−0.0180 (5)	0.0087 (4)	−0.0030 (5)
O4	0.0250 (5)	0.0474 (7)	0.0343 (6)	−0.0012 (5)	−0.0036 (4)	0.0024 (5)
O5	0.0398 (6)	0.0412 (7)	0.0275 (5)	−0.0149 (5)	0.0103 (5)	−0.0031 (5)
O6	0.0545 (8)	0.0298 (5)	0.0286 (5)	0.0002 (5)	0.0116 (5)	−0.0078 (4)
C3	0.0247 (6)	0.0278 (6)	0.0241 (6)	−0.0011 (5)	0.0015 (5)	−0.0018 (5)
C2	0.0252 (6)	0.0316 (7)	0.0234 (6)	0.0017 (5)	0.0052 (5)	0.0003 (5)
C5	0.0221 (6)	0.0232 (6)	0.0279 (6)	0.0029 (5)	0.0040 (5)	0.0030 (5)
C1	0.0243 (6)	0.0297 (7)	0.0320 (7)	−0.0002 (6)	0.0068 (5)	−0.0057 (6)
C4	0.0251 (6)	0.0347 (8)	0.0273 (7)	0.0015 (6)	0.0019 (5)	0.0049 (6)
O8	0.0297 (6)	0.0652 (9)	0.0419 (7)	0.0035 (6)	−0.0015 (5)	0.0122 (7)
C10	0.0301 (8)	0.0244 (7)	0.0494 (10)	0.0011 (6)	0.0071 (7)	0.0036 (6)
C6	0.0234 (7)	0.0330 (8)	0.0467 (9)	−0.0006 (6)	0.0029 (6)	0.0045 (7)
C9	0.0468 (11)	0.0280 (8)	0.0661 (13)	0.0109 (8)	0.0110 (10)	0.0070 (8)
C8	0.0408 (10)	0.0490 (11)	0.0707 (15)	0.0220 (9)	0.0123 (10)	0.0172 (11)
C7	0.0211 (7)	0.0548 (12)	0.0698 (14)	0.0061 (8)	0.0050 (8)	0.0140 (11)

Geometric parameters (Å, º) top

S1—O4	1.4347 (13)	C3—H3B	0.9700
S1—O2	1.4438 (11)	C2—C1	1.507 (2)
S1—O3	1.4754 (11)	C2—H2A	0.9700
S1—O1	1.5553 (12)	C2—H2B	0.9700
S2—O8	1.4378 (14)	C5—C6	1.377 (2)
S2—O6	1.4387 (12)	C5—C10	1.380 (2)
S2—O7	1.4647 (12)	C1—H1C	0.9700
S2—O5	1.5542 (12)	C1—H1D	0.9700
N2—C5	1.4799 (18)	C4—H4A	0.9700
N2—C2	1.5027 (19)	C4—H4B	0.9700
N2—C3	1.5041 (18)	C10—C9	1.388 (2)
N2—H2	0.9100	C10—H10	0.9300
N1—C4	1.485 (2)	C6—C7	1.383 (2)
N1—C1	1.491 (2)	C6—H6	0.9300
N1—H1A	0.9000	C9—C8	1.373 (3)
N1—H1B	0.9000	C9—H9	0.9300
O1—H1	0.8200	C8—C7	1.383 (3)
O5—H5	0.8200	C8—H8	0.9300
C3—C4	1.507 (2)	C7—H7	0.9300
C3—H3A	0.9700

O4—S1—O2	115.31 (8)	C1—C2—H2A	109.4
O4—S1—O3	111.75 (7)	N2—C2—H2B	109.4
O2—S1—O3	110.49 (7)	C1—C2—H2B	109.4
O4—S1—O1	108.60 (8)	H2A—C2—H2B	108.0
O2—S1—O1	104.35 (7)	C6—C5—C10	122.13 (15)
O3—S1—O1	105.60 (7)	C6—C5—N2	117.99 (13)
O8—S2—O6	115.46 (9)	C10—C5—N2	119.87 (13)
O8—S2—O7	111.29 (8)	N1—C1—C2	109.67 (12)
O6—S2—O7	110.95 (7)	N1—C1—H1C	109.7
O8—S2—O5	107.90 (8)	C2—C1—H1C	109.7
O6—S2—O5	103.68 (7)	N1—C1—H1D	109.7
O7—S2—O5	106.89 (8)	C2—C1—H1D	109.7
C5—N2—C2	111.93 (11)	H1C—C1—H1D	108.2
C5—N2—C3	112.96 (11)	N1—C4—C3	109.71 (12)
C2—N2—C3	109.52 (11)	N1—C4—H4A	109.7
C5—N2—H2	107.4	C3—C4—H4A	109.7
C2—N2—H2	107.4	N1—C4—H4B	109.7
C3—N2—H2	107.4	C3—C4—H4B	109.7
C4—N1—C1	111.13 (12)	H4A—C4—H4B	108.2
C4—N1—H1A	109.4	C5—C10—C9	118.29 (17)
C1—N1—H1A	109.4	C5—C10—H10	120.9
C4—N1—H1B	109.4	C9—C10—H10	120.9
C1—N1—H1B	109.4	C5—C6—C7	118.74 (17)
H1A—N1—H1B	108.0	C5—C6—H6	120.6
S1—O1—H1	109.5	C7—C6—H6	120.6
S2—O5—H5	109.5	C8—C9—C10	120.33 (18)
N2—C3—C4	109.89 (12)	C8—C9—H9	119.8
N2—C3—H3A	109.7	C10—C9—H9	119.8
C4—C3—H3A	109.7	C9—C8—C7	120.56 (18)
N2—C3—H3B	109.7	C9—C8—H8	119.7
C4—C3—H3B	109.7	C7—C8—H8	119.7
H3A—C3—H3B	108.2	C8—C7—C6	119.95 (18)
N2—C2—C1	110.98 (12)	C8—C7—H7	120.0
N2—C2—H2A	109.4	C6—C7—H7	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82	1.80	2.6140 (17)	172
O5—H5···O7ⁱⁱ	0.82	1.80	2.6066 (18)	169
N1—H1A···O2ⁱⁱⁱ	0.90	2.23	2.8636 (19)	128
N1—H1A···O3^iv	0.90	2.30	3.0279 (19)	138
N1—H1B···O3	0.90	2.14	2.9251 (18)	145
N1—H1B···O2ⁱ	0.90	2.35	2.9892 (18)	128
N2—H2···O7	0.91	2.02	2.8216 (16)	146
N2—H2···O6ⁱⁱ	0.91	2.32	2.9037 (17)	122
C1—H1C···O8	0.97	2.59	3.500 (2)	156
C1—H1D···O2ⁱ	0.97	2.60	3.113 (2)	114
C3—H3A···O6ⁱⁱ	0.97	2.42	2.949 (2)	114
C3—H3B···O4	0.97	2.59	3.513 (2)	159
C6—H6···O7	0.93	2.55	3.246 (2)	132
C10—H10···O4	0.93	2.60	3.520 (2)	170

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N₂²⁺·2HSO₄⁻
M_r	358.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.535 (6), 10.996 (2), 7.631 (2)
β (°)	99.86 (2)
V (Å³)	1449.7 (7)
Z	4
Radiation type	Ag Kα, λ = 0.56083 Å
µ (mm⁻¹)	0.22
Crystal size (mm)	0.5 × 0.4 × 0.1

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8212, 7100, 4535
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.836

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.127, 1.03
No. of reflections	7100
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.46

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-32 for Windows (Farrugia, 1998), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.82	1.80	2.6140 (17)	171.8
O5—H5···O7ⁱⁱ	0.82	1.80	2.6066 (18)	169.0
N1—H1A···O2ⁱⁱⁱ	0.90	2.23	2.8636 (19)	127.5
N1—H1A···O3^iv	0.90	2.30	3.0279 (19)	138.1
N1—H1B···O3	0.90	2.14	2.9251 (18)	145.4
N1—H1B···O2ⁱ	0.90	2.35	2.9892 (18)	128.2
N2—H2···O7	0.91	2.02	2.8216 (16)	145.8
N2—H2···O6ⁱⁱ	0.91	2.32	2.9037 (17)	121.8

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+2, y−1/2, −z+3/2; (iv) −x+2, −y+1, −z+1.

Acknowledgements

We would like to acknowledge the support provided by the Secretary of State for Scientific Research and Technology of Tunisia.

References

Arbuckle, W., Kennedy, A. R. & Morrison, C. A. (2009). Acta Cryst. E65, o1768–o1769. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ben Gharbia, I., Kefi, R., Rayes, A. & Ben Nasr, C. (2005). Z. Kristallogr. 220, 333–334. Google Scholar
Blessing, R. H. (1986). Acta Cryst. B42, 613–621. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Brown, I. D. (1976). Acta Cryst. A32, 24–31. CrossRef IUCr Journals Web of Science Google Scholar
Cohen, M. R., Hinsch, E., Palkoski, Z., Vergona, R., Urbano, S. & Sztokalo, J. (1982). J. Pharmcol. Exp. Ther. 223, 110–115. CAS Google Scholar
Conrado, D. J., Verli, H., Neves, G., Fraga, C. A., Barreiro, E. J., Rates, S. M. & Dalla-Costa, T. (2008). J. Pharm. Pharmacol. 60, 699–707. Web of Science CrossRef PubMed CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1998). ORTEP-32 for Windows. University of Glasgow, Scotland. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Neves, G., Fenner, R., Heckler, A. P., Viana, A. F., Tasso, L., Menegatti, R., Fraga, C. A. M., Barreiro, E. J., Dalla-Costa, T. & Rates, S. M. K. (2003). Braz. J. Med. Biol. Res. 36, 625–629. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar