Dichloridobis[(S)-2-hydroxy­propion­amide-κ2O,O′]manganese(II)

Lemoine, P.; Viossat, B.; Brion, J.D.; Bekaert, A.

doi:10.1107/S1600536808004066

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page m471

doi:10.1107/S1600536808004066

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Dichloridobis[(S)-2-hydroxypropionamide-κ²O,O′]manganese(II)

Pascale Lemoine,^a ^* Bernard Viossat,^a Jean Daniel Brion ^b and Alain Bekaert ^b

^aLaboratoire de Cristallographie et RMN Biologiques, UMR 8015 CNRS, Faculté des Sciences Pharmaceutiques et Biologiques de Paris Descartes, 4 Avenue de l'Observatoire, 75270 Paris Cedex 06, France, and ^bUniversité de Paris XI, Faculté des Sciences Pharmaceutiques et Biologiques, Laboratoire de Chimie Thérapeutique BioCIS, UPRES-A 8076 CNRS, 5 Rue J. B. Clément, 92296 Châtenay-Malabry Cedex, France
^*Correspondence e-mail: lemoine@pharmacie.univ-paris5.fr

(Received 17 December 2007; accepted 8 February 2008; online 13 February 2008)

In the title compound, [MnCl₂(C₃H₇NO₂)₂], the Mn^II ion is bound to two Cl atoms and to four O atoms from two lactamide molecules which act as bidentate ligands, giving rise to a highly distorted octahedral coordination geometry. The axial positions are occupied by one Cl atom and one O (hydroxy) atom. The values of the cis bond angles at the Mn atom are in the range 72.33 (5)–100.17 (6)°. Of the two possible coordination modes (N,O- or O,O-bidentate) in metal complexes with lactamide or its derivatives described in the literature, the title compound exhibits the O,O-bidentate mode. In the crystal structure, monomeric manganese(II) complexes are linked by several N—H⋯Cl, O—H⋯Cl and O—H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For related literature, see: Bekaert et al. (2005 , 2007 ); Chen et al. (2006 ); Girma et al. (2005 ).

Experimental

Crystal data

[MnCl₂(C₃H₇NO₂)₂]
M_r = 304.03
Monoclinic, P 2₁
a = 6.312 (2) Å
b = 11.718 (3) Å
c = 8.268 (2) Å
β = 99.47 (1)°
V = 603.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.53 mm⁻¹
T = 293 (2) K
0.18 × 0.16 × 0.12 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3659 measured reflections
1836 independent reflections
1803 reflections with I > 2σ(I)
R_int = 0.030
3 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.061
S = 1.11
1836 reflections
161 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱ	0.92 (4)	2.40 (4)	3.310 (2)	170 (3)
N1—H1B⋯Cl2ⁱⁱ	0.80 (3)	2.60 (4)	3.360 (2)	159 (3)
O2—H2⋯Cl1ⁱⁱⁱ	0.89 (4)	2.26 (4)	3.1250 (17)	164 (3)
O7—H7⋯O1^iv	0.86 (4)	1.83 (4)	2.676 (2)	167 (3)
N6—H6A⋯Cl2^v	0.80 (4)	2.65 (4)	3.439 (2)	168 (3)
N6—H6B⋯Cl2^vi	0.87 (4)	2.54 (4)	3.409 (3)	172 (4)
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) x+1, y, z; (v) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (vi) $[-x, y+{\script{1\over 2}}, -z]$ .

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: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004066/im2054sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004066/im2054Isup2.hkl

checkCIF report

Comment top

Metal-containing proteins have been studied in relation to severe diseases. Alzheimer's and mad cow diseases imply metal-protein interactions and metalloproteases are implied in cancer dispersion and angiotensin converting enzyme (ACE) in blood pressure control. For these reasons, amide-metal complexes have attracted much interest (lactamide = 2-hydroxypropionamide). Recently, we have been engaged in the synthesis and structural characterization of the cationic complexes [Zn(lactamide)₃]²⁺ (Bekaert et al., 2005) and [B(lactamide)₂]⁺ (Bekaert et al., 2007). Moreover, manganese is known to participate in a variety of biological reactions. We therefore studied and now report a new dichloromanganese(II) complex with lactamide ligands. Compound (1) (Fig. 1) contains one monomeric octahedral manganese complex, [Mn(C₃H₇NO₂)Cl₂]. Manganese is surrounded by two bidentate lactamide ligands each coordinating via the carbonyl O atom O1 (or O6) and the hydroxy atom O2 (or O7) and two Cl ligands. The complex exhibits a highly distorted octahedral geometry around the Mn^II ion with the apical positions occupied by O2 and Cl2 aoms (O2—Mn—Cl2: 167.63 (4) °). The Mn atom lies 0.270 (1) Å out of the basal plane (Cl1/O1/O2/O6). The degree of deviation from an ideal octahedron is appreciable, with the cis angles of the octahedron ranging from 72.33 (5) to 100.17 (6) °. The two equatorial Mn—O bond lengths for oxygen amide atoms are 2.196 (1) and 2.185 (2) Å for O1 and O6, respectively, being close to those reported for [Mn(O-acrylamide)₄Cl₂] with a similar coordination of Mn^II [2.186 (1) Å] (Girma et al., 2005). Among the Mn—O (hydroxy) distances the equatorial Mn—O7 [2.174 (2) Å], is close to precedent values but very different from the axial Mn—O2 bond length [2.247 (2) Å]. The Mn—Cl bond distances [2.4535 (7) and 2.4786 (7) Å] are in good agreement with those found in similar octahedral Mn^II complexes like e.g. in [chloridobis(1,10- phenanthroline)(trichloroacetato)manganese(II)] [2.4374 (2) Å] (Chen et al., 2006). Among the two possible coordination modes (N,O or O,O) in metal complexes with lactamide or its derivatives described in the literature, the title compound presents the O,O mode as in the before cited [Zn(lactamide)₃]²⁺ and [B(lactamide)₂]⁺ complexes. The packing is charaterized by numerous interactions that can be considered as hydrogen bonds since they correspond to H–A contacts significantly shorter than the sum of the van der Waals radii (Table 1). In particular, [Mn(lactamide)₂Cl₂] complexes are connected by N—H···Cl, N—H···O and O—H···O hydrogen bonds, generating a three dimensional network (Figures 1 and 2).

Related literature top

For related literature, see: Bekaert et al. (2005, 2007); Chen et al. (2006); Girma et al. (2005).

Experimental top

Enantiomerically pure (S)-lactamide ((S)-2-hydroxypropionamide, 2.22 g, 25 mmol) is dissolved in 20 ml of hot ethanoic acid and manganese(II) dichloride (1.26 g, 10 mmol) is added to this solution. The solution is kept at room temperature for 72 h. Pink crystals of the title compound slowly appear in the solution, whereupon crystals suitable for X-ray diffraction were obtained.

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: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular view of the complex showing the atomic numbering and some N—H···Cl, O—H···Cl and O—H···O hydrogen bonds as dotted lines. Displacement ellipsoids are displayed at the 50% probability level. Symmetry code: a: (x - 1, y, z), b: (x, y, 1 + z), c: (1 - x, 1/2 + y, 1 - z), d: (1 + x, y, z), e: (1 - x, 1/2 + y, -z), f: (-x, 1/2 + y, -z), g: (x, y, z - 1), h: (-x, y - 1/2, -z) and i: (1 - x, y - 1/2, -z).

Fig. 2. Stereoscopic view of molecular the stacking including hydrogen bonds.

Dichloridobis[(S)-2-hydroxypropionamide-κ²O,O']manganese(II) top

Crystal data top

[MnCl₂(C₃H₇NO₂)₂]	F(000) = 310
M_r = 304.03	D_x = 1.674 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.312 (2) Å	θ = 3.0–8.9°
b = 11.718 (3) Å	µ = 1.53 mm⁻¹
c = 8.268 (2) Å	T = 293 K
β = 99.47 (1)°	Parallelepiped, pink
V = 603.2 (3) Å³	0.18 × 0.16 × 0.12 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.030
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.5°
Graphite monochromator	h = −8→8
ω–2θ scans	k = 0→16
3659 measured reflections	l = −11→11
1836 independent reflections	3 standard reflections every 60 min
1803 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0412P)²] where P = (F_o² + 2F_c²)/3
1836 reflections	(Δ/σ)_max < 0.001
161 parameters	Δρ_max = 0.35 e Å⁻³
1 restraint	Δρ_min = −0.51 e Å⁻³

Crystal data top

[MnCl₂(C₃H₇NO₂)₂]	V = 603.2 (3) Å³
M_r = 304.03	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.312 (2) Å	µ = 1.53 mm⁻¹
b = 11.718 (3) Å	T = 293 K
c = 8.268 (2) Å	0.18 × 0.16 × 0.12 mm
β = 99.47 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.030
3659 measured reflections	3 standard reflections every 60 min
1836 independent reflections	intensity decay: none
1803 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.022	1 restraint
wR(F²) = 0.061	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.35 e Å⁻³
1836 reflections	Δρ_min = −0.51 e Å⁻³
161 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
Mn1	0.28185 (4)	0.57573 (2)	0.28850 (3)	0.02305 (8)
Cl1	0.43848 (9)	0.40435 (4)	0.43841 (7)	0.03790 (12)
Cl2	0.13344 (8)	0.49119 (5)	0.02244 (5)	0.03331 (11)
O1	−0.0161 (2)	0.56907 (16)	0.39299 (14)	0.0286 (3)
N1	−0.1127 (4)	0.5206 (3)	0.6322 (2)	0.0513 (7)
H1A	−0.228 (6)	0.480 (3)	0.576 (4)	0.041 (3)*
H1B	−0.079 (6)	0.526 (3)	0.729 (4)	0.041 (3)*
C1	0.0131 (3)	0.5736 (2)	0.54632 (19)	0.0287 (3)
O2	0.3440 (2)	0.66403 (14)	0.53298 (18)	0.0333 (3)
H2	0.406 (6)	0.730 (3)	0.563 (4)	0.041 (3)*
C2	0.1925 (3)	0.6459 (2)	0.6381 (2)	0.0310 (4)
H20	0.253 (5)	0.609 (3)	0.728 (4)	0.041 (3)*
C3	0.1005 (7)	0.7558 (4)	0.6897 (6)	0.0699 (11)
H3A	0.2141	0.8023	0.7469	0.105*
H3B	−0.0016	0.7396	0.7607	0.105*
H3C	0.0304	0.7958	0.5944	0.105*
O6	0.2428 (2)	0.74635 (14)	0.1810 (2)	0.0332 (3)
O7	0.5940 (2)	0.63077 (16)	0.2395 (2)	0.0414 (4)
H7	0.726 (6)	0.617 (3)	0.278 (4)	0.041 (3)*
N6	0.3807 (4)	0.89164 (17)	0.0554 (3)	0.0392 (4)
H6A	0.483 (6)	0.919 (4)	0.025 (4)	0.041 (3)*
H6B	0.255 (6)	0.924 (4)	0.036 (4)	0.041 (3)*
C6	0.3966 (3)	0.79133 (17)	0.1305 (2)	0.0277 (3)
C7	0.6136 (3)	0.73241 (18)	0.1480 (2)	0.0297 (4)
H70	0.715 (6)	0.786 (4)	0.211 (4)	0.041 (3)*
C8	0.6730 (4)	0.7018 (2)	−0.0168 (3)	0.0399 (5)
H8A	0.8105	0.6647	−0.0006	0.060*
H8B	0.6795	0.7700	−0.0802	0.060*
H8C	0.5665	0.6513	−0.0741	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.02205 (12)	0.02285 (12)	0.02441 (12)	0.00065 (10)	0.00426 (8)	0.00154 (9)
Cl1	0.0368 (2)	0.0242 (2)	0.0493 (3)	0.00502 (18)	−0.0032 (2)	0.00568 (18)
Cl2	0.0347 (2)	0.0378 (2)	0.02582 (17)	0.00258 (19)	0.00027 (15)	−0.00370 (18)
O1	0.0222 (5)	0.0419 (7)	0.0209 (5)	−0.0006 (6)	0.0014 (4)	0.0020 (6)
N1	0.0488 (11)	0.0796 (18)	0.0257 (7)	−0.0334 (12)	0.0060 (7)	0.0035 (9)
C1	0.0253 (7)	0.0362 (9)	0.0238 (7)	−0.0043 (9)	0.0018 (6)	0.0018 (8)
O2	0.0348 (7)	0.0298 (7)	0.0379 (7)	−0.0101 (6)	0.0134 (6)	−0.0101 (6)
C2	0.0313 (8)	0.0385 (9)	0.0225 (6)	−0.0089 (8)	0.0026 (6)	−0.0010 (7)
C3	0.070 (2)	0.0620 (19)	0.089 (2)	−0.0148 (18)	0.046 (2)	−0.0384 (19)
O6	0.0284 (6)	0.0280 (6)	0.0442 (7)	0.0033 (6)	0.0094 (6)	0.0096 (6)
O7	0.0202 (6)	0.0455 (9)	0.0578 (9)	0.0047 (6)	0.0043 (6)	0.0309 (8)
N6	0.0410 (10)	0.0281 (8)	0.0509 (10)	0.0063 (8)	0.0147 (8)	0.0128 (8)
C6	0.0295 (8)	0.0233 (8)	0.0299 (7)	0.0013 (6)	0.0041 (7)	0.0022 (6)
C7	0.0240 (7)	0.0279 (9)	0.0363 (8)	−0.0020 (7)	0.0020 (7)	0.0081 (7)
C8	0.0421 (11)	0.0343 (10)	0.0466 (11)	0.0121 (9)	0.0172 (9)	0.0065 (9)

Geometric parameters (Å, º) top

Mn1—O7	2.1739 (16)	C3—H3A	0.9600
Mn1—O6	2.1853 (17)	C3—H3B	0.9600
Mn1—O1	2.1964 (14)	C3—H3C	0.9600
Mn1—O2	2.2471 (15)	O6—C6	1.236 (3)
Mn1—Cl2	2.4535 (7)	O7—C7	1.427 (2)
Mn1—Cl1	2.4786 (7)	O7—H7	0.86 (4)
O1—C1	1.252 (2)	N6—C6	1.326 (3)
N1—C1	1.307 (3)	N6—H6A	0.80 (4)
N1—H1A	0.92 (4)	N6—H6B	0.87 (4)
N1—H1B	0.80 (3)	C6—C7	1.519 (3)
C1—C2	1.515 (3)	C7—C8	1.514 (3)
O2—C2	1.410 (2)	C7—H70	0.98 (4)
O2—H2	0.89 (4)	C8—H8A	0.9600
C2—C3	1.503 (4)	C8—H8B	0.9600
C2—H20	0.89 (3)	C8—H8C	0.9600

O7—Mn1—O6	72.40 (6)	C1—C2—H20	109 (2)
O7—Mn1—O1	160.90 (7)	C2—C3—H3A	109.5
O6—Mn1—O1	98.39 (6)	C2—C3—H3B	109.5
O7—Mn1—O2	90.10 (7)	H3A—C3—H3B	109.5
O6—Mn1—O2	86.32 (7)	C2—C3—H3C	109.5
O1—Mn1—O2	72.33 (5)	H3A—C3—H3C	109.5
O7—Mn1—Cl2	100.17 (6)	H3B—C3—H3C	109.5
O6—Mn1—Cl2	90.23 (5)	C6—O6—Mn1	119.04 (14)
O1—Mn1—Cl2	96.49 (4)	C7—O7—Mn1	120.43 (12)
O2—Mn1—Cl2	167.63 (4)	C7—O7—H7	101 (2)
O7—Mn1—Cl1	91.97 (5)	Mn1—O7—H7	137 (2)
O6—Mn1—Cl1	162.47 (5)	C6—N6—H6A	120 (3)
O1—Mn1—Cl1	94.10 (5)	C6—N6—H6B	118 (3)
O2—Mn1—Cl1	85.82 (5)	H6A—N6—H6B	122 (4)
Cl2—Mn1—Cl1	100.56 (3)	O6—C6—N6	122.2 (2)
C1—O1—Mn1	113.83 (11)	O6—C6—C7	121.32 (18)
C1—N1—H1A	118 (2)	N6—C6—C7	116.43 (19)
C1—N1—H1B	115 (3)	O7—C7—C8	109.57 (18)
H1A—N1—H1B	127 (3)	O7—C7—C6	105.93 (15)
O1—C1—N1	121.9 (2)	C8—C7—C6	112.02 (17)
O1—C1—C2	120.30 (17)	O7—C7—H70	111 (2)
N1—C1—C2	117.71 (16)	C8—C7—H70	113.3 (18)
C2—O2—Mn1	116.74 (12)	C6—C7—H70	105 (2)
C2—O2—H2	106 (2)	C7—C8—H8A	109.5
Mn1—O2—H2	131 (2)	C7—C8—H8B	109.5
O2—C2—C3	112.3 (2)	H8A—C8—H8B	109.5
O2—C2—C1	107.58 (15)	C7—C8—H8C	109.5
C3—C2—C1	109.2 (2)	H8A—C8—H8C	109.5
O2—C2—H20	110 (2)	H8B—C8—H8C	109.5
C3—C2—H20	108 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.92 (4)	2.40 (4)	3.310 (2)	170 (3)
N1—H1B···Cl2ⁱⁱ	0.80 (3)	2.60 (4)	3.360 (2)	159 (3)
O2—H2···Cl1ⁱⁱⁱ	0.89 (4)	2.26 (4)	3.1250 (17)	164 (3)
O7—H7···O1^iv	0.86 (4)	1.83 (4)	2.676 (2)	167 (3)
N6—H6A···Cl2^v	0.80 (4)	2.65 (4)	3.439 (2)	168 (3)
N6—H6B···Cl2^vi	0.87 (4)	2.54 (4)	3.409 (3)	172 (4)

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

Experimental details

Crystal data
Chemical formula	[MnCl₂(C₃H₇NO₂)₂]
M_r	304.03
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	6.312 (2), 11.718 (3), 8.268 (2)
β (°)	99.47 (1)
V (Å³)	603.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.53
Crystal size (mm)	0.18 × 0.16 × 0.12

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3659, 1836, 1803
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.061, 1.11
No. of reflections	1836
No. of parameters	161
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.51

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.92 (4)	2.40 (4)	3.310 (2)	170 (3)
N1—H1B···Cl2ⁱⁱ	0.80 (3)	2.60 (4)	3.360 (2)	159 (3)
O2—H2···Cl1ⁱⁱⁱ	0.89 (4)	2.26 (4)	3.1250 (17)	164 (3)
O7—H7···O1^iv	0.86 (4)	1.83 (4)	2.676 (2)	167 (3)
N6—H6A···Cl2^v	0.80 (4)	2.65 (4)	3.439 (2)	168 (3)
N6—H6B···Cl2^vi	0.87 (4)	2.54 (4)	3.409 (3)	172 (4)

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

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bekaert, A., Lemoine, P., Brion, J. D. & Viossat, B. (2005). Acta Cryst. C61, m76–m77. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bekaert, A., Lemoine, P., Brion, J. D. & Viossat, B. (2007). Acta Cryst. E63, o3187–o3189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chen, L., Wang, X.-W., Chen, F.-P., Chen, Y. & Chen, J.-Z. (2006). Acta Cryst. E62, m1743–m1745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Version 5.1. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Girma, K. B., Lorentz, V., Blaurock, S. & Edelmann, F. T. (2005). Z. Anorg. Allg. Chem. 631, 2763–2769. Web of Science CSD CrossRef CAS Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar

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