2,2′-(Disulfanedi­yl)dianilinium dichloride dihydrate

Bouchareb, H.; Boudraa, M.; Bouacida, S.; Merazig, H.

doi:10.1107/S1600536813015742

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1078-o1079

https://doi.org/10.1107/S1600536813015742

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2,2′-(Disulfanediyl)dianilinium dichloride dihydrate

Hasna Bouchareb,^a Mhamed Boudraa,^a Sofiane Bouacida ^a,^b ^* and Hocin Merazig ^a

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000, Algeria, and ^bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 5 June 2013; accepted 5 June 2013; online 12 June 2013)

In the title hydrated molecular salt, C₁₂H₁₄N₂S₂²⁺·2Cl⁻·2H₂O, the dihedral angle between the benzene rings in the dication is 9.03 (17)° and the C—S—S—C torsion angle is 96.8 (2)°. The crystal packing can be described as alternating organic and anionic water layers lying parallel to (100), which are linked by N—H⋯Cl and N—H⋯O hydrogen bonds. O—H⋯Cl hydrogen bonds and aromatic π–π stacking interactions [centroid–centroid separation = 3.730 (3) Å] are also observed.

Related literature

For related structures and background to disulfides, see: Benmebarek et al. (2012 , 2013 ). For related structures, see: Tang et al. (2011 ); Goh et al. (2010 ); Song & Fan (2009 ).

Experimental

Crystal data

C₁₂H₁₄N₂S₂²⁺·2Cl⁻·2H₂O
M_r = 357.32
Orthorhombic, P n a 2₁
a = 17.826 (7) Å
b = 13.358 (5) Å
c = 7.120 (3) Å
V = 1695.4 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 150 K
0.16 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
10760 measured reflections
3584 independent reflections
2409 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.134
S = 1.05
3584 reflections
195 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.47 e Å⁻³
Absolute structure: Flack (1983 ), 1369 Friedel pairs
Flack parameter: −0.12 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1Wⁱ	0.89	1.83	2.723 (6)	178
N1—H1B⋯Cl2ⁱ	0.89	2.24	3.108 (4)	166
N1—H1C⋯Cl1ⁱ	0.89	2.25	3.103 (4)	160
N2—H2A⋯O2Wⁱⁱ	0.89	1.84	2.727 (6)	177
N2—H2B⋯Cl2ⁱⁱⁱ	0.89	2.26	3.111 (4)	160
N2—H2C⋯Cl2	0.89	2.30	3.157 (4)	163
O2W—H4W⋯Cl2	0.86 (5)	2.36 (5)	3.157 (5)	155 (5)
O2W—H3W⋯Cl1^iv	0.85 (5)	2.23 (5)	3.078 (4)	171 (6)
O1W—H1W⋯Cl1^v	0.85 (5)	2.27 (5)	3.096 (5)	167 (5)
O1W—H2W⋯Cl1^iv	0.86 (5)	2.27 (5)	3.127 (5)	176 (7)
Symmetry codes: (i) $[-x+2, -y, z+{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[-x+2, -y, z-{\script{1\over 2}}]$ ; (iv) x, y, z+1; (v) $[-x+2, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2011 ); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015742/hb7089sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015742/hb7089Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015742/hb7089Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies on the synthesis, structures and biological activity of organometallic complexes based in sulfur (Benmebarek et al. 2012 and Benmebarek et al. 2013), we have synthesized and determined the crystal structure of the title compound (I), (Fig. 1). In the cation the S—S bond length is 2.061 (2)°, indicating the single bond character similar to that found in 4,4'-diaminophenyldisulfide (Tang et al., 2011; Goh et al. 2010). In the diprotoned 2,2'-dithiodianiline moiety, the dihedral angle between the benzene rings is 9.03 (17)°; different to that found in [67.82 (9)°] 1,2-Bis(2-nitrophenyl)disulfane (Song & Fan, 2009) and [39.9 (2)°]4,4'- diaminophenyldisulfide (Tang et al., 2011). The crystal packing can be described as alternating layers parallel to (100) plane, wich are linked toghether by N—H···Cl and N—H···O interactions involving molecule of water and anions chloride. O—H···Cl hydrogen bond and π–π stacking are observed.

Related literature top

For related structures and background to disulfides, see: Benmebarek et al. (2012, 2013). For related structures, see: Tang et al. (2011); Goh et al. (2010); Song & Fan (2009).

Experimental top

2-Aminobenzenethiol (0.1 mmol) was added to concentrated HCl (2 ml) and transfered into a 23 ml teflon-lined stainless steel autoclave and heated at 120° C for 3 days. Then the autoclave was cooled to room temperature at 10°/h. Colourless prisms were collected, washed with ethanol and dried in air at room temperature.

Structure description top

For related structures and background to disulfides, see: Benmebarek et al. (2012, 2013). For related structures, see: Tang et al. (2011); Goh et al. (2010); Song & Fan (2009).

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Diagram packing of (I) viwed via c axis showing hydrogen bonding in alterning layers.

2,2'-(Disulfanediyl)dianilinium dichloride dihydrate top

Crystal data top

C₁₂H₁₄N₂S₂²⁺·2Cl⁻·2H₂O	F(000) = 744
M_r = 357.32	D_x = 1.4 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2698 reflections
a = 17.826 (7) Å	θ = 2.3–28.5°
b = 13.358 (5) Å	µ = 0.63 mm⁻¹
c = 7.120 (3) Å	T = 150 K
V = 1695.4 (12) Å³	Prism, colourless
Z = 4	0.16 × 0.13 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	2409 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.097
Graphite monochromator	θ_max = 28.8°, θ_min = 2.8°
φ and ω scans	h = −24→23
10760 measured reflections	k = −18→18
3584 independent reflections	l = −9→8

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)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0595P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3584 reflections	Δρ_max = 0.58 e Å⁻³
195 parameters	Δρ_min = −0.47 e Å⁻³
6 restraints	Absolute structure: Flack (1983), 1369 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.12 (12)

Crystal data top

C₁₂H₁₄N₂S₂²⁺·2Cl⁻·2H₂O	V = 1695.4 (12) Å³
M_r = 357.32	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 17.826 (7) Å	µ = 0.63 mm⁻¹
b = 13.358 (5) Å	T = 150 K
c = 7.120 (3) Å	0.16 × 0.13 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	2409 reflections with I > 2σ(I)
10760 measured reflections	R_int = 0.097
3584 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.134	Δρ_max = 0.58 e Å⁻³
S = 1.05	Δρ_min = −0.47 e Å⁻³
3584 reflections	Absolute structure: Flack (1983), 1369 Friedel pairs
195 parameters	Absolute structure parameter: −0.12 (12)
6 restraints

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
Cl2	0.98060 (6)	0.10914 (8)	1.19390 (17)	0.0269 (3)
S1	0.86675 (9)	−0.10667 (11)	1.3286 (2)	0.0412 (4)
Cl1	0.99242 (8)	0.36455 (10)	0.7389 (2)	0.0411 (4)
S2	0.85864 (8)	−0.15845 (11)	1.0567 (2)	0.0395 (4)
O2W	0.9096 (2)	0.1819 (3)	1.5764 (6)	0.0381 (10)
H3W	0.935 (3)	0.233 (3)	1.609 (9)	0.057*
H4W	0.937 (3)	0.150 (4)	1.497 (7)	0.057*
N2	0.8933 (2)	0.0331 (3)	0.8354 (6)	0.0267 (9)
H2A	0.8991	0.0831	0.7542	0.04*
H2B	0.9208	−0.019	0.7989	0.04*
H2C	0.9082	0.0528	0.9489	0.04*
C21	0.7911 (3)	−0.0781 (4)	0.9473 (8)	0.0286 (12)
O1W	1.0599 (3)	0.4223 (3)	1.3483 (6)	0.0534 (12)
H1W	1.043 (4)	0.476 (3)	1.302 (9)	0.08*
H2W	1.039 (4)	0.406 (4)	1.453 (6)	0.08*
N1	0.9146 (2)	−0.2839 (3)	1.5749 (6)	0.0282 (10)
H1A	0.9242	−0.3284	1.6647	0.042*
H1B	0.9388	−0.2271	1.5996	0.042*
H1C	0.9298	−0.3079	1.4647	0.042*
C26	0.8140 (2)	0.0039 (3)	0.8427 (7)	0.0218 (10)
C14	0.7102 (3)	−0.3103 (4)	1.6647 (8)	0.0317 (12)
H14	0.6782	−0.3509	1.7342	0.038*
C12	0.7275 (3)	−0.1730 (4)	1.4523 (8)	0.0332 (13)
H12	0.7073	−0.1212	1.3811	0.04*
C25	0.7627 (3)	0.0625 (3)	0.7478 (8)	0.0272 (11)
H25	0.7787	0.1168	0.6768	0.033*
C15	0.7858 (3)	−0.3249 (3)	1.6726 (7)	0.0268 (11)
H15	0.8055	−0.3753	1.7482	0.032*
C11	0.8050 (3)	−0.1876 (3)	1.4566 (7)	0.0255 (11)
C23	0.6638 (3)	−0.0391 (4)	0.8641 (8)	0.0395 (14)
H23	0.6128	−0.0526	0.8741	0.047*
C24	0.6876 (3)	0.0396 (4)	0.7590 (8)	0.0345 (12)
H24	0.6528	0.0784	0.6943	0.041*
C16	0.8335 (3)	−0.2645 (3)	1.5676 (7)	0.0237 (10)
C13	0.6811 (3)	−0.2350 (4)	1.5534 (8)	0.0381 (13)
H13	0.6294	−0.2262	1.5468	0.046*
C22	0.7156 (3)	−0.1002 (4)	0.9572 (8)	0.0354 (13)
H22	0.6992	−0.1554	1.0255	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0198 (5)	0.0332 (6)	0.0276 (7)	−0.0025 (5)	−0.0034 (6)	0.0026 (5)
S1	0.0445 (9)	0.0428 (7)	0.0364 (8)	−0.0186 (7)	−0.0119 (8)	0.0133 (6)
Cl1	0.0422 (8)	0.0424 (7)	0.0388 (9)	−0.0023 (5)	−0.0125 (7)	0.0027 (6)
S2	0.0429 (8)	0.0445 (7)	0.0310 (8)	0.0133 (6)	0.0111 (8)	0.0111 (6)
O2W	0.040 (2)	0.043 (2)	0.031 (3)	−0.0078 (17)	−0.002 (2)	0.0002 (18)
N2	0.029 (2)	0.030 (2)	0.021 (2)	0.0051 (16)	−0.001 (2)	−0.0027 (17)
C21	0.034 (3)	0.032 (3)	0.019 (3)	0.001 (2)	0.004 (3)	−0.007 (2)
O1W	0.072 (3)	0.051 (3)	0.038 (3)	0.019 (2)	0.003 (3)	−0.003 (2)
N1	0.030 (2)	0.030 (2)	0.025 (3)	−0.0031 (17)	0.000 (2)	−0.0016 (18)
C26	0.022 (2)	0.028 (2)	0.015 (3)	0.0005 (18)	0.003 (2)	−0.0089 (19)
C14	0.028 (3)	0.044 (3)	0.023 (3)	−0.007 (2)	0.002 (3)	−0.004 (2)
C12	0.038 (3)	0.035 (3)	0.027 (3)	0.004 (2)	−0.002 (3)	−0.006 (2)
C25	0.030 (3)	0.030 (2)	0.021 (3)	0.005 (2)	−0.003 (3)	−0.006 (2)
C15	0.033 (3)	0.026 (2)	0.021 (3)	−0.0076 (19)	0.000 (3)	−0.0043 (19)
C11	0.030 (3)	0.028 (2)	0.019 (3)	−0.008 (2)	0.002 (2)	−0.006 (2)
C23	0.026 (3)	0.062 (4)	0.030 (4)	−0.006 (3)	0.002 (3)	−0.015 (3)
C24	0.027 (3)	0.046 (3)	0.030 (3)	0.005 (2)	−0.008 (3)	−0.008 (2)
C16	0.024 (2)	0.027 (2)	0.020 (3)	−0.0046 (18)	0.001 (2)	−0.010 (2)
C13	0.024 (3)	0.052 (3)	0.038 (4)	0.000 (2)	0.009 (3)	−0.017 (3)
C22	0.030 (3)	0.049 (3)	0.028 (3)	−0.008 (3)	0.005 (3)	−0.003 (2)

Geometric parameters (Å, º) top

S1—C11	1.792 (5)	C14—C15	1.364 (6)
S1—S2	2.061 (2)	C14—C13	1.380 (8)
S2—C21	1.791 (5)	C14—H14	0.93
O2W—H3W	0.86 (2)	C12—C13	1.375 (8)
O2W—H4W	0.86 (2)	C12—C11	1.396 (7)
N2—C26	1.468 (6)	C12—H12	0.93
N2—H2A	0.89	C25—C24	1.375 (7)
N2—H2B	0.89	C25—H25	0.93
N2—H2C	0.89	C15—C16	1.391 (7)
C21—C22	1.380 (7)	C15—H15	0.93
C21—C26	1.386 (7)	C11—C16	1.391 (7)
O1W—H1W	0.852 (19)	C23—C24	1.358 (8)
O1W—H2W	0.858 (19)	C23—C22	1.399 (8)
N1—C16	1.469 (6)	C23—H23	0.93
N1—H1A	0.89	C24—H24	0.93
N1—H1B	0.89	C13—H13	0.93
N1—H1C	0.89	C22—H22	0.93
C26—C25	1.380 (7)

C11—S1—S2	103.43 (17)	C13—C12—H12	120
C21—S2—S1	104.74 (18)	C11—C12—H12	120
H3W—O2W—H4W	106 (6)	C24—C25—C26	119.4 (5)
C26—N2—H2A	109.5	C24—C25—H25	120.3
C26—N2—H2B	109.5	C26—C25—H25	120.3
H2A—N2—H2B	109.5	C14—C15—C16	119.9 (5)
C26—N2—H2C	109.5	C14—C15—H15	120
H2A—N2—H2C	109.5	C16—C15—H15	120
H2B—N2—H2C	109.5	C16—C11—C12	118.5 (4)
C22—C21—C26	118.9 (5)	C16—C11—S1	120.7 (4)
C22—C21—S2	120.3 (4)	C12—C11—S1	120.8 (4)
C26—C21—S2	120.6 (4)	C24—C23—C22	120.4 (5)
H1W—O1W—H2W	114 (3)	C24—C23—H23	119.8
C16—N1—H1A	109.5	C22—C23—H23	119.8
C16—N1—H1B	109.5	C23—C24—C25	120.5 (5)
H1A—N1—H1B	109.5	C23—C24—H24	119.7
C16—N1—H1C	109.5	C25—C24—H24	119.7
H1A—N1—H1C	109.5	C15—C16—C11	120.7 (4)
H1B—N1—H1C	109.5	C15—C16—N1	118.7 (4)
C25—C26—C21	121.0 (4)	C11—C16—N1	120.6 (4)
C25—C26—N2	118.1 (4)	C12—C13—C14	120.9 (5)
C21—C26—N2	120.8 (4)	C12—C13—H13	119.5
C15—C14—C13	120.0 (5)	C14—C13—H13	119.5
C15—C14—H14	120	C21—C22—C23	119.6 (5)
C13—C14—H14	120	C21—C22—H22	120.2
C13—C12—C11	120.0 (5)	C23—C22—H22	120.2

C11—S1—S2—C21	96.8 (2)	C22—C23—C24—C25	−2.1 (8)
S1—S2—C21—C22	−87.5 (5)	C26—C25—C24—C23	0.7 (8)
S1—S2—C21—C26	96.2 (4)	C14—C15—C16—C11	1.2 (7)
C22—C21—C26—C25	−0.7 (8)	C14—C15—C16—N1	−178.3 (4)
S2—C21—C26—C25	175.7 (4)	C12—C11—C16—C15	−0.3 (7)
C22—C21—C26—N2	177.1 (4)	S1—C11—C16—C15	177.5 (4)
S2—C21—C26—N2	−6.5 (6)	C12—C11—C16—N1	179.1 (4)
C21—C26—C25—C24	0.7 (7)	S1—C11—C16—N1	−3.0 (6)
N2—C26—C25—C24	−177.1 (5)	C11—C12—C13—C14	2.1 (8)
C13—C14—C15—C16	−0.4 (7)	C15—C14—C13—C12	−1.2 (8)
C13—C12—C11—C16	−1.3 (7)	C26—C21—C22—C23	−0.8 (8)
C13—C12—C11—S1	−179.1 (4)	S2—C21—C22—C23	−177.2 (4)
S2—S1—C11—C16	103.3 (4)	C24—C23—C22—C21	2.2 (9)
S2—S1—C11—C12	−78.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wⁱ	0.89	1.83	2.723 (6)	178
N1—H1B···Cl2ⁱ	0.89	2.24	3.108 (4)	166
N1—H1C···Cl1ⁱ	0.89	2.25	3.103 (4)	160
N2—H2A···O2Wⁱⁱ	0.89	1.84	2.727 (6)	177
N2—H2B···Cl2ⁱⁱⁱ	0.89	2.26	3.111 (4)	160
N2—H2C···Cl2	0.89	2.30	3.157 (4)	163
O2W—H4W···Cl2	0.86 (5)	2.36 (5)	3.157 (5)	155 (5)
O2W—H3W···Cl1^iv	0.85 (5)	2.23 (5)	3.078 (4)	171 (6)
O1W—H1W···Cl1^v	0.85 (5)	2.27 (5)	3.096 (5)	167 (5)
O1W—H2W···Cl1^iv	0.86 (5)	2.27 (5)	3.127 (5)	176 (7)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄N₂S₂²⁺·2Cl⁻·2H₂O
M_r	357.32
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	150
a, b, c (Å)	17.826 (7), 13.358 (5), 7.120 (3)
V (Å³)	1695.4 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.16 × 0.13 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10760, 3584, 2409
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.134, 1.05
No. of reflections	3584
No. of parameters	195
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.47
Absolute structure	Flack (1983), 1369 Friedel pairs
Absolute structure parameter	−0.12 (12)

Computer programs: APEX2 (Bruker, 2011), SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1Wⁱ	0.89	1.83	2.723 (6)	178
N1—H1B···Cl2ⁱ	0.89	2.24	3.108 (4)	166
N1—H1C···Cl1ⁱ	0.89	2.25	3.103 (4)	160
N2—H2A···O2Wⁱⁱ	0.89	1.84	2.727 (6)	177
N2—H2B···Cl2ⁱⁱⁱ	0.89	2.26	3.111 (4)	160
N2—H2C···Cl2	0.89	2.30	3.157 (4)	163
O2W—H4W···Cl2	0.86 (5)	2.36 (5)	3.157 (5)	155 (5)
O2W—H3W···Cl1^iv	0.85 (5)	2.23 (5)	3.078 (4)	171 (6)
O1W—H1W···Cl1^v	0.85 (5)	2.27 (5)	3.096 (5)	167 (5)
O1W—H2W···Cl1^iv	0.86 (5)	2.27 (5)	3.127 (5)	176 (7)

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

Acknowledgements

This work is supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université de Constantine, Algeria. Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie - Algérie) via the PNR programme for financial support.

References

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