Bis(cytosinium) aqua­penta­chlorido­indate(III)

Bouacida, S.; Belhouas, R.; Fantazi, B.; Boudaren, C.; Roisnel, T.

doi:10.1107/S1600536811004235

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m317-m318

doi:10.1107/S1600536811004235

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Bis(cytosinium) aquapentachloridoindate(III)

Sofiane Bouacida,^a ^*‡ Ratiba Belhouas,^a Boubakeur Fantazi,^a Chaouki Boudaren ^a and Thierry Roisnel ^b

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria, and ^bCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du général Leclerc, 35042 Rennes, France.
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 1 February 2011; accepted 3 February 2011; online 12 February 2011)

The asymmetric unit of the title compound, (C₄H₆N₃O)₂[InCl₅(H₂O)], comprises two independent cytosinium cations and an aquapentachloridoindate anion. The In^III ion is in a slightly distorted octahedral coordination geometry. In the crystal, alternating layers of cations and anions are arranged along [010] and are linked via intermolecular N—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming sheets parallel to (001). Additional stabilization within these sheeets is provided by weak intermolecular C—H⋯O interactions.

Related literature

For related structures, see: Bouacida (2008 ); Bouacida et al. (2005 , 2009 ); Casellato et al. (1995 ); Cherouana et al. (2003 ). For standard bond lengths see: Allen et al. (1987 ).

Experimental

Crystal data

(C₄H₆N₃O)₂[InCl₅(H₂O)]
M_r = 534.32
Triclinic, $[P \overline 1]$
a = 6.863 (1) Å
b = 10.487 (2) Å
c = 12.765 (2) Å
α = 104.608 (1)°
β = 97.998 (1)°
γ = 98.121 (1)°
V = 865.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.16 mm⁻¹
T = 295 K
0.18 × 0.09 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer
18109 measured reflections
3933 independent reflections
3572 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.048
S = 1.07
3929 reflections
214 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯Cl1ⁱ	0.80 (3)	2.52 (3)	3.3033 (17)	167 (2)
N2A—H2A⋯Cl4ⁱⁱ	0.86	2.41	3.2185 (18)	156
N2B—H2B⋯Cl2ⁱⁱⁱ	0.86	2.47	3.2774 (18)	157
O1W—H2W⋯Cl2ⁱⁱ	0.78 (3)	2.49 (3)	3.2667 (18)	174 (3)
N6A—H6A⋯Cl3ⁱⁱⁱ	0.86	2.37	3.2104 (17)	164
N6B—H6B⋯Cl5ⁱⁱ	0.86	2.38	3.2160 (18)	163
N7A—H71A⋯O1Aⁱ	0.86	2.19	2.965 (3)	150
N7B—H71B⋯O1Wⁱⁱⁱ	0.86	2.38	3.226 (3)	168
N7A—H72A⋯Cl1ⁱⁱ	0.86	2.69	3.471 (2)	152
N7B—H72B⋯O1B^iv	0.86	2.22	2.987 (3)	149
C4A—H4A⋯O1Aⁱ	0.93	2.30	3.068 (3)	140
C4B—H4B⋯O1B^iv	0.93	2.28	3.051 (3)	140
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x+1, y, z.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ) and DIAMOND (Brandenburg et al., 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004235/lh5204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004235/lh5204Isup2.hkl

checkCIF report

Comment top

The title compound, was prepared as part of our ongoing studies of hydrogen-bonding interaction in the crystal structures of protonated amines (Bouacida, 2008; Bouacida et al., 2009). The asymmetric unit of the title compound (I) is shown in Fig. 1. The bond distances (Allen et al. 1987) and angles are within the ranges of accepted values. In the title compound the imine N atom is protonated as in other related structures (Bouacida et al., 2005; Casellato, et al. 1995; Cherouana et al., 2003). The In atom is six-coordinated (by five chlorine atoms and one water molecule) forming a slightly-distorted octahedral geometry. In the crystal structure alternating layers of cations and anions are arranged along [010] and are linked via intermolecular N—H···O, O—H···Cl and N—H···Cl hydrogen bonds to form a two-dimensional sheets parallel to (001) (see Fig. 2). Additional stabilization within these sheeets is provided by weak intermolecular C—H···O interactions.

Related literature top

For related structures, see: Bouacida et al. (2005, 2008, 2009); Casellato et al. (1995); Cherouana et al. (2003). For standard bond lengths see: Allen et al. (1987).

Experimental top

A solution of 1 mmol InCl₃ and 2 mmol cytosine in hydrochloric acid was slowly evaporated to dryness over a period of two weeks yielding red crystals suitable for X-ray diffraction.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and DIAMOND (Brandenburg et al., 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure with hydrogen bonds shown as dashed lines.

Bis(cytosinium) aquapentachloridoindate(III) top

Crystal data top

(C₄H₆N₃O)₂[InCl₅(H2O)]	Z = 2
M_r = 534.32	F(000) = 524
Triclinic, P1	D_x = 2.051 Mg m⁻³
a = 6.863 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.487 (2) Å	Cell parameters from 8762 reflections
c = 12.765 (2) Å	θ = 3.1–27.5°
α = 104.608 (1)°	µ = 2.16 mm⁻¹
β = 97.998 (1)°	T = 295 K
γ = 98.121 (1)°	Needle, red
V = 865.3 (2) Å³	0.18 × 0.09 × 0.07 mm

Data collection top

Nonius KappaCCD diffractometer	R_int = 0.032
Graphite monochromator	θ_max = 27.6°, θ_min = 1.7°
CCD rotation images, thick slices scans	h = −8→8
18109 measured reflections	k = −13→13
3933 independent reflections	l = −16→16
3572 reflections with I > 2σ(I)

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)] = 0.02	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0229P)² + 0.0464P] where P = (F_o² + 2F_c²)/3
3929 reflections	(Δ/σ)_max = 0.002
214 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

(C₄H₆N₃O)₂[InCl₅(H2O)]	γ = 98.121 (1)°
M_r = 534.32	V = 865.3 (2) Å³
Triclinic, P1	Z = 2
a = 6.863 (1) Å	Mo Kα radiation
b = 10.487 (2) Å	µ = 2.16 mm⁻¹
c = 12.765 (2) Å	T = 295 K
α = 104.608 (1)°	0.18 × 0.09 × 0.07 mm
β = 97.998 (1)°

Data collection top

Nonius KappaCCD diffractometer	3572 reflections with I > 2σ(I)
18109 measured reflections	R_int = 0.032
3933 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.02	0 restraints
wR(F²) = 0.048	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.35 e Å⁻³
3929 reflections	Δρ_min = −0.61 e Å⁻³
214 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.

4 bad reflections were omitted from the refinement

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

	x	y	z	U_iso*/U_eq
In1	0.550968 (18)	0.423292 (12)	0.265050 (10)	0.02044 (5)
Cl2	0.68990 (8)	0.33651 (5)	0.42094 (4)	0.03022 (11)
Cl3	0.35973 (7)	0.19643 (4)	0.16412 (4)	0.02749 (11)
Cl4	0.36901 (7)	0.51814 (5)	0.13047 (4)	0.03375 (12)
Cl5	0.68860 (8)	0.65285 (5)	0.38414 (5)	0.03400 (12)
Cl1	0.84669 (8)	0.39953 (6)	0.17617 (5)	0.03882 (13)
N2B	0.6503 (2)	−0.06652 (16)	0.62369 (13)	0.0249 (4)
H2B	0.5921	−0.1469	0.6175	0.03*
O1B	0.3547 (2)	0.00633 (15)	0.63256 (14)	0.0405 (4)
N6A	0.3443 (2)	0.01389 (16)	0.88504 (14)	0.0282 (4)
H6A	0.411	−0.0502	0.8804	0.034*
O1A	0.6221 (2)	0.16293 (15)	0.89141 (15)	0.0455 (4)
N6B	0.6325 (2)	0.15524 (17)	0.63714 (15)	0.0316 (4)
H6B	0.5662	0.2195	0.641	0.038*
N7B	0.9460 (2)	−0.14472 (16)	0.62174 (14)	0.0304 (4)
H71B	0.8827	−0.2227	0.619	0.037*
H72B	1.0728	−0.1321	0.6225	0.037*
C4B	0.9437 (3)	0.08585 (19)	0.63066 (16)	0.0264 (4)
H4B	1.08	0.1051	0.6303	0.032*
C3B	0.8491 (3)	−0.04516 (19)	0.62486 (15)	0.0227 (4)
C4A	0.0348 (3)	0.08195 (19)	0.89372 (16)	0.0258 (4)
H4A	−0.1012	0.0624	0.8951	0.031*
C5B	0.8318 (3)	0.1819 (2)	0.63676 (17)	0.0302 (5)
H5B	0.8922	0.2685	0.6408	0.036*
C1B	0.5332 (3)	0.0312 (2)	0.63174 (16)	0.0266 (4)
C3A	0.1280 (3)	0.21374 (18)	0.90100 (15)	0.0234 (4)
O1W	0.2642 (2)	0.42641 (16)	0.35025 (13)	0.0319 (3)
H1W	0.166 (4)	0.433 (2)	0.312 (2)	0.048*
H2W	0.272 (4)	0.487 (3)	0.402 (2)	0.048*
C5A	0.1454 (3)	−0.01407 (19)	0.88486 (16)	0.0267 (4)
H3A	0.0849	−0.1015	0.8785	0.032*
C1A	0.4435 (3)	0.1381 (2)	0.89219 (17)	0.0284 (4)
N7A	0.0296 (3)	0.31296 (17)	0.90638 (15)	0.0354 (4)
H72A	0.091	0.3911	0.9082	0.042*
H71A	−0.0963	0.2999	0.9081	0.042*
N2A	0.3263 (2)	0.23531 (16)	0.89832 (14)	0.0258 (4)
H2A	0.3828	0.3148	0.9006	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
In1	0.01960 (8)	0.01626 (7)	0.02516 (8)	0.00200 (5)	0.00384 (5)	0.00607 (5)
Cl2	0.0331 (3)	0.0272 (2)	0.0304 (3)	0.0062 (2)	0.0002 (2)	0.0106 (2)
Cl3	0.0290 (3)	0.0184 (2)	0.0310 (3)	0.00087 (18)	0.0023 (2)	0.00312 (19)
Cl4	0.0287 (3)	0.0312 (3)	0.0428 (3)	0.0015 (2)	−0.0020 (2)	0.0198 (2)
Cl5	0.0313 (3)	0.0185 (2)	0.0444 (3)	−0.0001 (2)	−0.0013 (2)	0.0017 (2)
Cl1	0.0277 (3)	0.0490 (3)	0.0454 (3)	0.0106 (2)	0.0166 (2)	0.0159 (3)
N2B	0.0211 (8)	0.0216 (8)	0.0346 (9)	0.0037 (6)	0.0062 (7)	0.0118 (7)
O1B	0.0207 (8)	0.0379 (9)	0.0675 (11)	0.0080 (7)	0.0129 (7)	0.0187 (8)
N6A	0.0253 (9)	0.0235 (8)	0.0384 (10)	0.0089 (7)	0.0066 (8)	0.0101 (7)
O1A	0.0206 (8)	0.0371 (9)	0.0813 (13)	0.0066 (7)	0.0145 (8)	0.0175 (9)
N6B	0.0244 (9)	0.0256 (9)	0.0501 (11)	0.0096 (7)	0.0088 (8)	0.0162 (8)
N7B	0.0255 (9)	0.0268 (9)	0.0386 (10)	0.0071 (7)	0.0055 (8)	0.0072 (8)
C4B	0.0183 (9)	0.0304 (11)	0.0312 (11)	0.0022 (8)	0.0048 (8)	0.0113 (9)
C3B	0.0229 (10)	0.0257 (10)	0.0193 (9)	0.0051 (8)	0.0034 (7)	0.0060 (8)
C4A	0.0180 (9)	0.0301 (11)	0.0288 (11)	0.0011 (8)	0.0043 (8)	0.0093 (8)
C5B	0.0268 (11)	0.0241 (10)	0.0402 (12)	−0.0012 (8)	0.0051 (9)	0.0135 (9)
C1B	0.0215 (10)	0.0310 (11)	0.0306 (11)	0.0079 (8)	0.0062 (8)	0.0122 (9)
C3A	0.0212 (9)	0.0230 (9)	0.0243 (10)	0.0035 (8)	0.0038 (8)	0.0041 (8)
O1W	0.0262 (8)	0.0365 (9)	0.0297 (8)	0.0082 (7)	0.0045 (6)	0.0022 (6)
C5A	0.0263 (10)	0.0246 (10)	0.0276 (11)	−0.0005 (8)	0.0041 (8)	0.0079 (8)
C1A	0.0219 (10)	0.0284 (10)	0.0353 (11)	0.0061 (8)	0.0069 (9)	0.0078 (9)
N7A	0.0239 (9)	0.0265 (9)	0.0529 (12)	0.0052 (7)	0.0076 (8)	0.0054 (8)
N2A	0.0191 (8)	0.0216 (8)	0.0372 (10)	0.0015 (6)	0.0062 (7)	0.0095 (7)

Geometric parameters (Å, º) top

In1—O1W	2.3776 (15)	N7B—H71B	0.86
In1—Cl1	2.4718 (6)	N7B—H72B	0.86
In1—Cl5	2.4720 (6)	C4B—C5B	1.344 (3)
In1—Cl4	2.4730 (6)	C4B—C3B	1.413 (3)
In1—Cl3	2.4787 (6)	C4B—H4B	0.93
In1—Cl2	2.5155 (6)	C4A—C5A	1.337 (3)
N2B—C3B	1.349 (2)	C4A—C3A	1.413 (3)
N2B—C1B	1.381 (2)	C4A—H4A	0.93
N2B—H2B	0.86	C5B—H5B	0.93
O1B—C1B	1.218 (2)	C3A—N7A	1.311 (2)
N6A—C5A	1.354 (2)	C3A—N2A	1.355 (2)
N6A—C1A	1.356 (3)	O1W—H1W	0.80 (2)
N6A—H6A	0.86	O1W—H2W	0.78 (3)
O1A—C1A	1.218 (2)	C5A—H3A	0.93
N6B—C5B	1.357 (2)	C1A—N2A	1.379 (2)
N6B—C1B	1.361 (2)	N7A—H72A	0.86
N6B—H6B	0.86	N7A—H71A	0.86
N7B—C3B	1.310 (2)	N2A—H2A	0.86

O1W—In1—Cl1	175.07 (4)	N7B—C3B—N2B	119.31 (17)
O1W—In1—Cl5	88.65 (4)	N7B—C3B—C4B	123.05 (17)
Cl1—In1—Cl5	95.26 (2)	N2B—C3B—C4B	117.64 (17)
O1W—In1—Cl4	86.45 (4)	C5A—C4A—C3A	118.82 (17)
Cl1—In1—Cl4	96.55 (2)	C5A—C4A—H4A	120.6
Cl5—In1—Cl4	89.56 (2)	C3A—C4A—H4A	120.6
O1W—In1—Cl3	80.65 (4)	C4B—C5B—N6B	121.53 (18)
Cl1—In1—Cl3	95.42 (2)	C4B—C5B—H5B	119.2
Cl5—In1—Cl3	169.296 (17)	N6B—C5B—H5B	119.2
Cl4—In1—Cl3	89.95 (2)	O1B—C1B—N6B	123.31 (18)
O1W—In1—Cl2	83.91 (4)	O1B—C1B—N2B	121.90 (18)
Cl1—In1—Cl2	93.21 (2)	N6B—C1B—N2B	114.78 (16)
Cl5—In1—Cl2	88.07 (2)	N7A—C3A—N2A	119.53 (17)
Cl4—In1—Cl2	170.125 (18)	N7A—C3A—C4A	122.86 (18)
Cl3—In1—Cl2	90.60 (2)	N2A—C3A—C4A	117.57 (17)
C3B—N2B—C1B	124.87 (16)	In1—O1W—H1W	114.4 (18)
C3B—N2B—H2B	117.6	In1—O1W—H2W	115.7 (19)
C1B—N2B—H2B	117.6	H1W—O1W—H2W	101 (2)
C5A—N6A—C1A	123.24 (17)	C4A—C5A—N6A	121.06 (18)
C5A—N6A—H6A	118.4	C4A—C5A—H3A	119.5
C1A—N6A—H6A	118.4	N6A—C5A—H3A	119.5
C5B—N6B—C1B	122.77 (17)	O1A—C1A—N6A	123.22 (18)
C5B—N6B—H6B	118.6	O1A—C1A—N2A	121.78 (18)
C1B—N6B—H6B	118.6	N6A—C1A—N2A	114.99 (17)
C3B—N7B—H71B	120	C3A—N7A—H72A	120
C3B—N7B—H72B	120	C3A—N7A—H71A	120
H71B—N7B—H72B	120	H72A—N7A—H71A	120
C5B—C4B—C3B	118.37 (18)	C3A—N2A—C1A	124.27 (16)
C5B—C4B—H4B	120.8	C3A—N2A—H2A	117.9
C3B—C4B—H4B	120.8	C1A—N2A—H2A	117.9

C1B—N2B—C3B—N7B	176.87 (18)	C5A—C4A—C3A—N7A	177.79 (19)
C1B—N2B—C3B—C4B	−2.5 (3)	C5A—C4A—C3A—N2A	0.1 (3)
C5B—C4B—C3B—N7B	−178.07 (19)	C3A—C4A—C5A—N6A	1.3 (3)
C5B—C4B—C3B—N2B	1.2 (3)	C1A—N6A—C5A—C4A	−1.1 (3)
C3B—C4B—C5B—N6B	−0.2 (3)	C5A—N6A—C1A—O1A	−179.4 (2)
C1B—N6B—C5B—C4B	0.2 (3)	C5A—N6A—C1A—N2A	−0.6 (3)
C5B—N6B—C1B—O1B	179.6 (2)	N7A—C3A—N2A—C1A	−179.71 (19)
C5B—N6B—C1B—N2B	−1.2 (3)	C4A—C3A—N2A—C1A	−2.0 (3)
C3B—N2B—C1B—O1B	−178.40 (19)	O1A—C1A—N2A—C3A	−179.1 (2)
C3B—N2B—C1B—N6B	2.4 (3)	N6A—C1A—N2A—C3A	2.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···Cl1ⁱ	0.80 (3)	2.52 (3)	3.3033 (17)	167 (2)
N2A—H2A···Cl4ⁱⁱ	0.86	2.41	3.2185 (18)	156
N2B—H2B···Cl2ⁱⁱⁱ	0.86	2.47	3.2774 (18)	157
O1W—H2W···Cl2ⁱⁱ	0.78 (3)	2.49 (3)	3.2667 (18)	174 (3)
N6A—H6A···Cl3ⁱⁱⁱ	0.86	2.37	3.2104 (17)	164
N6B—H6B···Cl5ⁱⁱ	0.86	2.38	3.2160 (18)	163
N7A—H71A···O1Aⁱ	0.86	2.19	2.965 (3)	150
N7B—H71B···O1Wⁱⁱⁱ	0.86	2.38	3.226 (3)	168
N7A—H72A···Cl1ⁱⁱ	0.86	2.69	3.471 (2)	152
N7B—H72B···O1B^iv	0.86	2.22	2.987 (3)	149
C4A—H4A···O1Aⁱ	0.93	2.30	3.068 (3)	140
C4B—H4B···O1B^iv	0.93	2.28	3.051 (3)	140

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

Experimental details

Crystal data
Chemical formula	(C₄H₆N₃O)₂[InCl₅(H2O)]
M_r	534.32
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.863 (1), 10.487 (2), 12.765 (2)
α, β, γ (°)	104.608 (1), 97.998 (1), 98.121 (1)
V (Å³)	865.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.16
Crystal size (mm)	0.18 × 0.09 × 0.07

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18109, 3933, 3572
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.02, 0.048, 1.07
No. of reflections	3929
No. of parameters	214
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.61

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and DIAMOND (Brandenburg et al., 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···Cl1ⁱ	0.80 (3)	2.52 (3)	3.3033 (17)	167 (2)
N2A—H2A···Cl4ⁱⁱ	0.86	2.41	3.2185 (18)	156
N2B—H2B···Cl2ⁱⁱⁱ	0.86	2.47	3.2774 (18)	157
O1W—H2W···Cl2ⁱⁱ	0.78 (3)	2.49 (3)	3.2667 (18)	174 (3)
N6A—H6A···Cl3ⁱⁱⁱ	0.86	2.37	3.2104 (17)	164
N6B—H6B···Cl5ⁱⁱ	0.86	2.38	3.2160 (18)	163
N7A—H71A···O1Aⁱ	0.86	2.19	2.965 (3)	150
N7B—H71B···O1Wⁱⁱⁱ	0.86	2.38	3.226 (3)	168
N7A—H72A···Cl1ⁱⁱ	0.86	2.69	3.471 (2)	152
N7B—H72B···O1B^iv	0.86	2.22	2.987 (3)	149
C4A—H4A···O1Aⁱ	0.93	2.30	3.068 (3)	140
C4B—H4B···O1B^iv	0.93	2.28	3.051 (3)	140

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

Footnotes

‡Current address: Département Sciences de la Matière, Facult des Sciences Exactes et Sciences de la Nature et de la Vie, Universit Larbi Ben M'hidi, Oum El Bouaghi 04000, Algeria.

Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, Algeria.

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