Bis(2-amino-1,3-benzothia­zol-3-ium) tetra­chloridozincate(II)

Kefi, R.; Jeanneau, E.; Lefebvre, F.; Ben Nasr, C.

doi:10.1107/S1600536811015753

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m654-m655

doi:10.1107/S1600536811015753

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Bis(2-amino-1,3-benzothiazol-3-ium) tetrachloridozincate(II)

Riadh Kefi,^a Erwann Jeanneau,^b Frédéric Lefebvre ^c and Cherif Ben Nasr ^a ^*

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisia, ^bUniverstié Lyon 1, Centre de Diffractométrie Henri Longchambon, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France, and ^cLaboratoire de Chimie Organometallique de Surface (LCOMS), École Supérieure de Chimie Physique Électronique, 69622 Villeurbanne Cedex, France
^*Correspondence e-mail: cherif_bennasr@yahoo.fr

(Received 8 March 2011; accepted 26 April 2011; online 7 May 2011)

The asymmetric unit of the title compound, (C₇H₇N₂S)₂[ZnCl₄], contains a network of 2-aminobenzothiazolium cations and tetrahedral [ZnCl₄]²⁻ anions. The crystal packing is influenced by cation-to-anion N—H⋯Cl and C—H⋯Cl hydrogen bonds. The [ZnCl₄]²⁻ anions have a distorded tetrahedral geometry. Intermolecular π–π stacking interactions are present between neighboring benzene rings, thiazole and benzene rings and neighboring thiazole rings [centroid–centroid distances = 3.711 (2), 3.554 (1), 3.536 (2) and 3.572 (1) Å].

Related literature

For common applications of organic–inorganic hybrid materials, see: Bringley & Rajeswaran (2006 ); Pierpont & Jung (1994 ); Dai et al. (2002 ). For the geometry around the zinc atom, see: Harrison (2005 ). For the weighting scheme used, see: Prince (1982 ); Watkin (1994 ) and for the extinction correction, see: Larson (1970 ).

Experimental

Crystal data

(C₇H₇N₂S)₂[ZnCl₄]
M_r = 509.61
Triclinic, $[P \overline 1]$
a = 7.543 (1) Å
b = 7.828 (1) Å
c = 17.109 (2) Å
α = 94.250 (1)°
β = 100.930 (1)°
γ = 92.465 (1)°
V = 987.5 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 110 K
0.49 × 0.23 × 0.14 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical [using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 ), implemented in CrysAlis PRO (Agilent, 2010 )] T_min = 0.498, T_max = 0.771
10196 measured reflections
4685 independent reflections
3630 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.111
S = 0.94
4685 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −1.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H81⋯Cl3ⁱ	0.88	2.43	3.190 (5)	145
N15—H151⋯Cl3	0.86	2.42	3.235 (5)	157
N15—H152⋯Cl2ⁱ	0.86	2.42	3.274 (5)	176
N25—H251⋯Cl5ⁱⁱ	0.86	2.41	3.215 (5)	155
N16—H161⋯Cl4ⁱⁱ	0.86	2.34	3.196 (5)	177
N16—H162⋯Cl2ⁱⁱⁱ	0.86	2.37	3.215 (5)	166
C20—H201⋯Cl2	0.93	2.69	3.473 (6)	142
C22—H221⋯Cl5^iv	0.94	2.78	3.701 (5)	167
C11—H111⋯Cl4^v	0.93	2.73	3.592 (6)	154
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+2; (iii) -x+1, -y+1, -z+2; (iv) x-1, y-1, z; (v) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015753/vn2006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015753/vn2006Isup2.hkl

checkCIF report

Comment top

Inorganic-organic hybrid compounds provide a class of materials displaying interesting technological importance (Bringley & Rajeswaran, 2006; Pierpont & Jung, 1994; Dai et al., 2002). We report the crystal structure of one such compound, (C₇H₇N₂S)₂[ZnCl₄] (I), formed from the reaction of 2-aminobenzothiazole with zinc chloride. As shown in Fig.1, only the nitrogen atom of the thiazole ring of the title compound is protonated, but not that of the amine group. Thus, to ensure charge equilibrium, the structure associates each tetrachlorizincate anion with two (2-aminobenzothiazolium) cations. Fig.2 shows that the atomic arrangement of the title hybrid material can be described as inorganic ZnCl₄^2- units isolated from each other by the organic cations. The different entities are held together by coulombic attraction and multiple hydrogen bonds to form a three dimensional network. The tetraclorozincate anion geometrical features show that the Zn—Cl bond lengths vary between 2.245 (1) and 2.282 (1) Å and the Cl—Zn—Cl angles range from 103.35 (5) to 112.21 (5) °. These values, which are in good agreement with those reported previously, clearly indicate that the [ZnCl₄]^2- anion has a slightly distorted tetrahedral stereochemistry (Harrison, 2005). Intermolecular π-π stacking interactions are present between neighboring phenyl rings (centroid-centroid distance = 3.711 (2) Å), thiazole-phenyl rings (centroid-centroid distance = 3.554 (1) Å) and thiazole-thiazole rings (centroid-centroid distances = 3.536 (2) and 3.572 (1) Å) (Fig. 3).

Related literature top

For common applications of organic–inorganic hybrid materials, see: Bringley & Rajeswaran (2006); Pierpont & Jung (1994); Dai et al. (2002). For the geometry around the zinc atom, see: Harrison (2005). For the weighting scheme used, see: Prince (1982); Watkin (1994) and for the extinction correction, see: Larson (1970).

Experimental top

A mixture of an aqueous solution of 2-aminobenzothiazole (3 mmol, 0.450 g), zinc chloride (1.5 mmol, 0.297 g) and HCl (10 ml, 0.3 M) in a Petri dish was slowly evaporated at room temperature. Colorless single crystals of the title compound were isolated after several days (yield 58%).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top

	Fig. 1. View of (I), showing 50% probability displacement ellipsoids and arbitrary spheres for the H atoms.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are denoted by dotted lines. ZnCl₄ is given in tetrahedral representation.
	Fig. 3. π–π stacking interactions in (C₇H₇N₂S)₂[ZnCl₄]. The centroids of the rings are indicated by orange spheres.

Bis(2-amino-1,3-benzothiazol-3-ium) tetrachloridozincate(II) top

Crystal data top

(C₇H₇N₂S)₂[ZnCl₄]	Z = 2
M_r = 509.61	F(000) = 512
Triclinic, P1	D_x = 1.714 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.543 (1) Å	Cell parameters from 3221 reflections
b = 7.828 (1) Å	θ = 3.4–29.4°
c = 17.109 (2) Å	µ = 2.00 mm⁻¹
α = 94.250 (1)°	T = 110 K
β = 100.930 (1)°	Plate, colorless
γ = 92.465 (1)°	0.49 × 0.23 × 0.14 mm
V = 987.5 (2) Å³

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	4685 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3630 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 10.4685 pixels mm^-1	θ_max = 29.5°, θ_min = 3.4°
ω scans	h = −9→9
Absorption correction: analytical [using a multifaceted crystal model based on expressions derived by Clark & Reid (1995), implemented in CrysAlis PRO (Agilent, 2010)]	k = −10→10
T_min = 0.498, T_max = 0.771	l = −22→23
10196 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A₀T₀(x) + A₁T₁(x) ··· + A_n-1]T_n-1(x)] where A_i are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] [1-(deltaF/6*sigmaF)²]² A_i are: 0.230E + 04 0.321E + 04 0.179E + 04 528.
wR(F²) = 0.111	(Δ/σ)_max = 0.001
S = 0.94	Δρ_max = 1.03 e Å⁻³
4685 reflections	Δρ_min = −1.23 e Å⁻³
227 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 20 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

(C₇H₇N₂S)₂[ZnCl₄]	γ = 92.465 (1)°
M_r = 509.61	V = 987.5 (2) Å³
Triclinic, P1	Z = 2
a = 7.543 (1) Å	Mo Kα radiation
b = 7.828 (1) Å	µ = 2.00 mm⁻¹
c = 17.109 (2) Å	T = 110 K
α = 94.250 (1)°	0.49 × 0.23 × 0.14 mm
β = 100.930 (1)°

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	4685 independent reflections
Absorption correction: analytical [using a multifaceted crystal model based on expressions derived by Clark & Reid (1995), implemented in CrysAlis PRO (Agilent, 2010)]	3630 reflections with I > 2σ(I)
T_min = 0.498, T_max = 0.771	R_int = 0.045
10196 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 0.94	Δρ_max = 1.03 e Å⁻³
4685 reflections	Δρ_min = −1.23 e Å⁻³
227 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.49814 (8)	0.31162 (7)	0.75071 (4)	0.0243
Cl2	0.29039 (16)	0.43801 (16)	0.81360 (8)	0.0274
Cl3	0.50293 (17)	0.47084 (17)	0.64494 (8)	0.0312
Cl4	0.43482 (19)	0.03141 (16)	0.71252 (8)	0.0327
Cl5	0.76785 (17)	0.33826 (17)	0.83422 (9)	0.0348
S6	0.80197 (17)	0.66813 (17)	0.54732 (8)	0.0271
C7	0.9702 (6)	0.6161 (6)	0.6239 (3)	0.0238
N8	1.1348 (6)	0.6629 (5)	0.6125 (3)	0.0270
C9	1.1369 (7)	0.7391 (6)	0.5413 (3)	0.0259
C10	0.9660 (7)	0.7508 (6)	0.4981 (3)	0.0274
C11	0.9378 (8)	0.8213 (7)	0.4244 (3)	0.0334
C12	1.0891 (9)	0.8761 (7)	0.3964 (4)	0.0399
C13	1.2610 (8)	0.8636 (7)	0.4407 (4)	0.0371
C14	1.2880 (7)	0.7940 (7)	0.5137 (4)	0.0332
N15	0.9376 (6)	0.5413 (6)	0.6864 (3)	0.0301
N16	0.4666 (6)	0.2078 (6)	1.1438 (3)	0.0318
C17	0.3739 (7)	0.1401 (6)	1.0765 (3)	0.0267
S18	0.33424 (17)	0.24680 (16)	0.98962 (8)	0.0267
C19	0.2084 (7)	0.0651 (7)	0.9370 (3)	0.0272
C20	0.1203 (7)	0.0453 (7)	0.8583 (3)	0.0289
C21	0.0273 (7)	−0.1091 (7)	0.8316 (3)	0.0305
C22	0.0266 (7)	−0.2424 (6)	0.8813 (3)	0.0298
C23	0.1155 (7)	−0.2224 (6)	0.9596 (3)	0.0279
C24	0.2056 (7)	−0.0673 (6)	0.9873 (3)	0.0258
N25	0.2989 (6)	−0.0203 (5)	1.0642 (3)	0.0256
H111	0.8216	0.8312	0.3963	0.0401*
H121	1.0765	0.9226	0.3472	0.0479*
H131	1.3614	0.9009	0.4205	0.0452*
H141	1.4023	0.7848	0.5425	0.0398*
H201	0.1216	0.1333	0.8250	0.0348*
H211	−0.0354	−0.1254	0.7796	0.0368*
H221	−0.0350	−0.3478	0.8606	0.0360*
H231	0.1136	−0.3105	0.9923	0.0341*
H152	1.0268	0.5160	0.7218	0.0362*
H162	0.5251	0.3062	1.1464	0.0382*
H161	0.4973	0.1448	1.1825	0.0382*
H151	0.8275	0.5082	0.6881	0.0364*
H81	1.2342	0.6334	0.6426	0.0335*
H251	0.3111	−0.0904	1.1014	0.0316*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0209 (3)	0.0234 (3)	0.0286 (3)	0.0006 (2)	0.0037 (2)	0.0055 (2)
Cl2	0.0251 (6)	0.0269 (6)	0.0310 (6)	0.0003 (5)	0.0074 (5)	0.0040 (5)
Cl3	0.0238 (6)	0.0367 (7)	0.0359 (7)	0.0048 (5)	0.0079 (5)	0.0140 (5)
Cl4	0.0414 (7)	0.0246 (6)	0.0303 (6)	−0.0007 (5)	0.0031 (5)	0.0032 (5)
Cl5	0.0256 (6)	0.0321 (7)	0.0434 (8)	−0.0064 (5)	−0.0049 (5)	0.0156 (6)
S6	0.0210 (6)	0.0287 (6)	0.0299 (6)	0.0014 (5)	0.0004 (5)	0.0036 (5)
C7	0.018 (2)	0.024 (2)	0.031 (3)	0.0051 (18)	0.0061 (19)	0.004 (2)
N8	0.022 (2)	0.025 (2)	0.034 (2)	0.0004 (16)	0.0037 (17)	0.0024 (18)
C9	0.028 (3)	0.024 (2)	0.028 (2)	0.0062 (19)	0.009 (2)	0.002 (2)
C10	0.032 (3)	0.021 (2)	0.028 (3)	0.003 (2)	0.004 (2)	−0.003 (2)
C11	0.045 (3)	0.025 (3)	0.029 (3)	−0.001 (2)	0.004 (2)	−0.001 (2)
C12	0.061 (4)	0.026 (3)	0.032 (3)	−0.009 (3)	0.013 (3)	−0.003 (2)
C13	0.043 (3)	0.029 (3)	0.044 (3)	0.002 (2)	0.023 (3)	−0.004 (2)
C14	0.026 (3)	0.030 (3)	0.045 (3)	0.001 (2)	0.010 (2)	0.001 (2)
N15	0.026 (2)	0.035 (2)	0.029 (2)	−0.0015 (18)	0.0020 (18)	0.0060 (19)
N16	0.034 (2)	0.028 (2)	0.032 (2)	−0.0031 (19)	0.0012 (19)	0.0066 (19)
C17	0.023 (2)	0.026 (2)	0.032 (3)	−0.0024 (19)	0.007 (2)	0.006 (2)
S18	0.0268 (6)	0.0231 (6)	0.0308 (6)	−0.0029 (5)	0.0068 (5)	0.0054 (5)
C19	0.021 (2)	0.029 (3)	0.034 (3)	0.0000 (19)	0.010 (2)	0.006 (2)
C20	0.028 (3)	0.027 (3)	0.035 (3)	0.002 (2)	0.011 (2)	0.005 (2)
C21	0.029 (3)	0.031 (3)	0.030 (3)	−0.007 (2)	0.008 (2)	−0.002 (2)
C22	0.029 (3)	0.019 (2)	0.041 (3)	−0.0046 (19)	0.010 (2)	−0.004 (2)
C23	0.028 (3)	0.022 (2)	0.036 (3)	−0.0003 (19)	0.011 (2)	0.004 (2)
C24	0.022 (2)	0.025 (2)	0.032 (3)	0.0034 (19)	0.011 (2)	0.003 (2)
N25	0.028 (2)	0.0190 (19)	0.031 (2)	0.0027 (16)	0.0072 (18)	0.0060 (17)

Geometric parameters (Å, º) top

Zn1—Cl2	2.2820 (14)	N15—H152	0.856
Zn1—Cl3	2.2770 (14)	N15—H151	0.865
Zn1—Cl4	2.2462 (14)	N16—C17	1.292 (7)
Zn1—Cl5	2.2452 (14)	N16—H162	0.865
S6—C7	1.728 (5)	N16—H161	0.858
S6—C10	1.750 (5)	C17—S18	1.741 (5)
C7—N8	1.333 (6)	C17—N25	1.340 (6)
C7—N15	1.315 (6)	S18—C19	1.762 (5)
N8—C9	1.397 (6)	C19—C20	1.379 (7)
N8—H81	0.876	C19—C24	1.398 (7)
C9—C10	1.369 (7)	C20—C21	1.372 (7)
C9—C14	1.378 (7)	C20—H201	0.926
C10—C11	1.398 (7)	C21—C22	1.394 (7)
C11—C12	1.383 (8)	C21—H211	0.922
C11—H111	0.926	C22—C23	1.375 (8)
C12—C13	1.384 (9)	C22—H221	0.940
C12—H121	0.932	C23—C24	1.372 (7)
C13—C14	1.384 (8)	C23—H231	0.920
C13—H131	0.934	C24—N25	1.385 (7)
C14—H141	0.917	N25—H251	0.865

Cl2—Zn1—Cl3	103.35 (5)	C7—N15—H152	119.0
Cl2—Zn1—Cl4	114.50 (5)	C7—N15—H151	119.2
Cl3—Zn1—Cl4	112.21 (6)	H152—N15—H151	121.4
Cl2—Zn1—Cl5	108.54 (6)	C17—N16—H162	120.4
Cl3—Zn1—Cl5	110.34 (5)	C17—N16—H161	119.8
Cl4—Zn1—Cl5	107.81 (6)	H162—N16—H161	117.3
C7—S6—C10	90.0 (2)	N16—C17—S18	123.7 (4)
S6—C7—N8	112.2 (4)	N16—C17—N25	124.7 (5)
S6—C7—N15	123.3 (4)	S18—C17—N25	111.6 (4)
N8—C7—N15	124.5 (5)	C17—S18—C19	90.6 (2)
C7—N8—C9	114.5 (4)	S18—C19—C20	128.4 (4)
C7—N8—H81	123.0	S18—C19—C24	110.2 (4)
C9—N8—H81	121.8	C20—C19—C24	121.4 (5)
N8—C9—C10	111.9 (5)	C19—C20—C21	117.2 (5)
N8—C9—C14	126.5 (5)	C19—C20—H201	121.4
C10—C9—C14	121.6 (5)	C21—C20—H201	121.4
S6—C10—C9	111.4 (4)	C20—C21—C22	121.5 (5)
S6—C10—C11	127.5 (4)	C20—C21—H211	119.3
C9—C10—C11	121.1 (5)	C22—C21—H211	119.2
C10—C11—C12	117.4 (6)	C21—C22—C23	121.1 (5)
C10—C11—H111	120.4	C21—C22—H221	119.2
C12—C11—H111	122.1	C23—C22—H221	119.7
C11—C12—C13	120.8 (6)	C22—C23—C24	117.9 (5)
C11—C12—H121	120.2	C22—C23—H231	120.7
C13—C12—H121	118.9	C24—C23—H231	121.4
C12—C13—C14	121.5 (5)	C19—C24—C23	120.9 (5)
C12—C13—H131	119.5	C19—C24—N25	112.3 (4)
C14—C13—H131	119.0	C23—C24—N25	126.8 (5)
C13—C14—C9	117.5 (5)	C24—N25—C17	115.3 (4)
C13—C14—H141	121.0	C24—N25—H251	122.4
C9—C14—H141	121.5	C17—N25—H251	122.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H81···Cl3ⁱ	0.88	2.43	3.190 (5)	145
N15—H151···Cl3	0.86	2.42	3.235 (5)	157
N15—H152···Cl2ⁱ	0.86	2.42	3.274 (5)	176
N25—H251···Cl5ⁱⁱ	0.86	2.41	3.215 (5)	155
N16—H161···Cl4ⁱⁱ	0.86	2.34	3.196 (5)	177
N16—H162···Cl2ⁱⁱⁱ	0.86	2.37	3.215 (5)	166
C20—H201···Cl2	0.93	2.69	3.473 (6)	142
C22—H221···Cl5^iv	0.94	2.78	3.701 (5)	167
C11—H111···Cl4^v	0.93	2.73	3.592 (6)	154

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

Experimental details

Crystal data
Chemical formula	(C₇H₇N₂S)₂[ZnCl₄]
M_r	509.61
Crystal system, space group	Triclinic, P1
Temperature (K)	110
a, b, c (Å)	7.543 (1), 7.828 (1), 17.109 (2)
α, β, γ (°)	94.250 (1), 100.930 (1), 92.465 (1)
V (Å³)	987.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.00
Crystal size (mm)	0.49 × 0.23 × 0.14

Data collection
Diffractometer	Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Analytical [using a multifaceted crystal model based on expressions derived by Clark & Reid (1995), implemented in CrysAlis PRO (Agilent, 2010)]
T_min, T_max	0.498, 0.771
No. of measured, independent and observed [I > 2σ(I)] reflections	10196, 4685, 3630
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.692

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.111, 0.94
No. of reflections	4685
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −1.23

Computer programs: CrysAlis PRO (Agilent, 2010), SIR97 (Altomare et al., 1999), CRYSTALS (Betteridge et al., 2003), DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H81···Cl3ⁱ	0.88	2.43	3.190 (5)	145
N15—H151···Cl3	0.86	2.42	3.235 (5)	157
N15—H152···Cl2ⁱ	0.86	2.42	3.274 (5)	176
N25—H251···Cl5ⁱⁱ	0.86	2.41	3.215 (5)	155
N16—H161···Cl4ⁱⁱ	0.86	2.34	3.196 (5)	177
N16—H162···Cl2ⁱⁱⁱ	0.86	2.37	3.215 (5)	166
C20—H201···Cl2	0.93	2.69	3.473 (6)	142
C22—H221···Cl5^iv	0.94	2.78	3.701 (5)	167
C11—H111···Cl4^v	0.93	2.73	3.592 (6)	154

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

Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bringley, J. F. & Rajeswaran, M. (2006). Acta Cryst. E62, m1304–m1305. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dai, J.-C., Wu, X.-T., Fu, Z.-Y., Cui, C.-P., Wu, S.-M., Du, W.-X., Wu, L.-M., Zhang, H.-H. & Sum, Q.-Q. (2002). Inorg. Chem. 41, 1391–1396. Web of Science CSD CrossRef PubMed CAS Google Scholar
Harrison, W. T. A. (2005). Acta Cryst. E61, m1951–m1952. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
Pierpont, C. G. & Jung, O. (1994). J. Am. Chem. Soc. 116, 2229–2230. Google Scholar
Prince, E. (1982). Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag Google Scholar
Watkin, D. (1994). Acta Cryst. A50, 411–437. CrossRef CAS Web of Science IUCr Journals Google Scholar