Bis(triphenyl­guanidinium) tetra­chlorido­cuprate(II)

Pereira Silva, P.S.; Martins, N.D.; Ramos Silva, M.; Matos Beja, A.

doi:10.1107/S1600536808023404

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1083

doi:10.1107/S1600536808023404

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Bis(triphenylguanidinium) tetrachloridocuprate(II)

P. S. Pereira Silva,^a N. D. Martins,^a M. Ramos Silva ^a and A. Matos Beja ^a ^*

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal
^*Correspondence e-mail: psidonio@pollux.fis.uc.pt

(Received 11 April 2008; accepted 24 July 2008; online 31 July 2008)

The structure of the title compound, (C₁₉H₁₈N₃)₂[CuCl₄], consists of square-planar [CuCl₄]²⁻ anions and triphenylguanidinium cations. The Cu^II ion occupies a crystallographic inversion centre. In the cation, the dihedral angles between the phenyl rings and the plane defined by the central guanidinium fragment are in the range 51.9 (4)–64.4 (3)°. N—H⋯Cl hydrogen bonds assemble the ions into infinite chains running along the b axis.

Related literature

For related literature, see: Bian et al. (2005 ); Kemme et al. (1988 ); Klement et al. (1995 ); Pereira Silva et al. (2006 ); Pereira Silva et al. (2007 ).

Experimental

Crystal data

(C₁₉H₁₈N₃)₂[CuCl₄]
M_r = 782.08
Monoclinic, P 2₁ /c
a = 11.5893 (13) Å
b = 8.2404 (9) Å
c = 22.364 (2) Å
β = 119.423 (7)°
V = 1860.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 (2) K
0.21 × 0.10 × 0.04 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.744, T_max = 0.964
27709 measured reflections
3304 independent reflections
1405 reflections with I > 2σ(I)
R_int = 0.164

Refinement

R[F² > 2σ(F²)] = 0.097
wR(F²) = 0.319
S = 1.05
3304 reflections
223 parameters
H-atom parameters constrained
Δρ_max = 1.28 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2ⁱ	0.86	2.28	3.126 (8)	167
N2—H2⋯Cl1ⁱⁱ	0.86	2.51	3.218 (8)	140
N3—H3⋯Cl1	0.86	2.44	3.253 (9)	159
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023404/er2054sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023404/er2054Isup2.hkl

checkCIF report

Comment top

Molecular based magnets, systems in which molecular orbitals are crucial in mediating the magnetic interaction, are often synthesized by mild-chemistry conditions. Furthermore, the molecules/ions often assemble in low dimensional compounds providing easier systems to study both theoretical and experimentally. Some systems are even classified as Single Molecule Magnets, since the organically bridged metal clusters, exhibit magnetic properties similar to those observed in conventional bulk magnets like remanence and hysteresis (Bian et al., 2005). The title compound, (I), Fig.1, was synthesized within a project aiming at developing new molecular based magnets. Compound (I) is built up from triphenylguanidinium cations and CuCl₄^2- anions. The CN₃ fragment of the guanidinium group in (I) is planar, as expected for sp² hybridization of the central C atom. The bond lengths C1—N1 [1.324 (12) Å], C1—N2 [1.332 (12) Å] and C1—N3 [1.347 (12) Å] are within the range expected for a delocalized C-N bond. The dihedral angles between the ring planes and the plane defined by the central guanidinium fragment are 51.9 (4)°(C2—C7), 59.8 (4)°(C8—C13) and 64.4 (3)°(C14—C19). The corresponding angles for other triphenylguanidinium salts reported in the literature are within the range 32.6 (3)–70.2 (3)° (Kemme et al., 1988; Klement et al., 1995; Pereira Silva et al., 2006, 2007). This variability attests the flexibility of the triphenylguanidinium cation. The Cu^II ion occupies a crystallographic inversion centre and the environment around the metal ion is square-planar. There are hydrogen bonds between all the NH groups and the Cl^- ions, each CuCl₄^2- anion being linked to four cations, forming infinite chains along the [010] direction (Fig. 2, Table 2).

Related literature top

For related literature, see: Bian et al. (2005); Kemme et al. (1988); Klement et al. (1995); Pereira Silva et al. (2006); Pereira Silva et al. (2007).

Experimental top

Copper(II) chloride dihydrate (Riedel-de-Haën, pro analysis >99%, 0.125 mmol) was dissolved in 50 ml of hot water and triphenylguanidine (TCI, 97%, 0.25 mmol) was dissolved in ethanol (50 ml). The two solutions were mixed and several drops of HCl (Merck, 37%) were added. The solution was left to evaporate at room temperature and pressure. Green single crystals of (I) were obtained from the solution after a few days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEPII (Spek,2003) plot of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram, viewed down the a axis, with the hydrogen bonds depicted as dashed lines. The phenyl rings have been omitted for clarity.

Bis(triphenylguanidinium) tetrachloridocuprate top

Crystal data top

(C₁₉H₁₈N₃)₂[CuCl₄]	F(000) = 806
M_r = 782.08	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1887 reflections
a = 11.5893 (13) Å	θ = 2.7–15.3°
b = 8.2404 (9) Å	µ = 0.91 mm⁻¹
c = 22.364 (2) Å	T = 293 K
β = 119.423 (7)°	Prism, green
V = 1860.3 (3) Å³	0.21 × 0.10 × 0.04 mm
Z = 2

Data collection top

Bruker APEX2 CCD area-detector diffractometer	3304 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.164
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→13
T_min = 0.744, T_max = 0.964	k = −9→9
27709 measured reflections	l = −26→26

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)] = 0.097	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.319	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1615P)² + 0.2636P] where P = (F_o² + 2F_c²)/3
3304 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 1.29 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

(C₁₉H₁₈N₃)₂[CuCl₄]	V = 1860.3 (3) Å³
M_r = 782.08	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5893 (13) Å	µ = 0.91 mm⁻¹
b = 8.2404 (9) Å	T = 293 K
c = 22.364 (2) Å	0.21 × 0.10 × 0.04 mm
β = 119.423 (7)°

Data collection top

Bruker APEX2 CCD area-detector diffractometer	3304 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1405 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.964	R_int = 0.164
27709 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.097	0 restraints
wR(F²) = 0.319	H-atom parameters constrained
S = 1.05	Δρ_max = 1.29 e Å⁻³
3304 reflections	Δρ_min = −0.52 e Å⁻³
223 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
Cu	0.5000	0.0000	0.0000	0.0567 (7)
Cl1	0.6357 (3)	−0.0354 (3)	0.11412 (14)	0.0719 (9)
Cl2	0.4205 (3)	0.2267 (4)	0.02411 (15)	0.0826 (11)
N1	0.7105 (8)	0.4791 (9)	0.0748 (4)	0.055 (2)
H1	0.6701	0.5646	0.0521	0.066*
N2	0.7200 (9)	0.5995 (10)	0.1697 (4)	0.062 (2)
H2	0.7380	0.6909	0.1576	0.075*
N3	0.7583 (8)	0.3232 (10)	0.1706 (4)	0.057 (2)
H3	0.7238	0.2389	0.1453	0.069*
C1	0.7289 (10)	0.4673 (11)	0.1380 (6)	0.055 (3)
C2	0.7497 (12)	0.3671 (13)	0.0409 (6)	0.060 (3)
C3	0.8688 (11)	0.2853 (14)	0.0731 (6)	0.069 (3)
H3A	0.9255	0.2991	0.1199	0.083*
C4	0.9037 (14)	0.1834 (15)	0.0360 (7)	0.085 (4)
H4	0.9849	0.1303	0.0577	0.102*
C5	0.8197 (15)	0.1595 (17)	−0.0327 (8)	0.084 (4)
H5	0.8431	0.0888	−0.0574	0.101*
C6	0.7024 (15)	0.2395 (16)	−0.0646 (6)	0.086 (4)
H6	0.6462	0.2265	−0.1115	0.103*
C7	0.6666 (12)	0.3400 (14)	−0.0272 (6)	0.074 (3)
H7	0.5842	0.3903	−0.0489	0.089*
C8	0.6834 (11)	0.6040 (13)	0.2223 (5)	0.059 (3)
C9	0.7498 (11)	0.7120 (13)	0.2771 (6)	0.066 (3)
H9	0.8164	0.7788	0.2792	0.079*
C10	0.7153 (13)	0.7180 (15)	0.3276 (6)	0.079 (4)
H10	0.7582	0.7892	0.3644	0.094*
C11	0.6171 (13)	0.6182 (15)	0.3234 (7)	0.073 (3)
H11	0.5943	0.6208	0.3579	0.087*
C12	0.5536 (11)	0.5173 (14)	0.2705 (6)	0.067 (3)
H12	0.4874	0.4504	0.2687	0.081*
C13	0.5842 (11)	0.5110 (13)	0.2195 (6)	0.065 (3)
H13	0.5369	0.4424	0.1823	0.078*
C14	0.8391 (11)	0.2945 (12)	0.2415 (5)	0.054 (3)
C15	0.9571 (13)	0.3811 (16)	0.2788 (7)	0.077 (3)
H15	0.9813	0.4584	0.2567	0.092*
C16	1.0364 (12)	0.3537 (17)	0.3468 (8)	0.079 (4)
H16	1.1129	0.4146	0.3721	0.095*
C17	1.0011 (17)	0.233 (2)	0.3775 (6)	0.099 (5)
H17	1.0568	0.2110	0.4237	0.118*
C18	0.8876 (15)	0.1465 (16)	0.3424 (6)	0.088 (4)
H18	0.8648	0.0666	0.3641	0.106*
C19	0.8083 (12)	0.1796 (13)	0.2748 (6)	0.066 (3)
H19	0.7300	0.1213	0.2503	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0701 (13)	0.0335 (10)	0.0702 (13)	0.0039 (9)	0.0374 (10)	0.0044 (8)
Cl1	0.088 (2)	0.0415 (16)	0.0687 (18)	0.0019 (14)	0.0247 (17)	−0.0021 (13)
Cl2	0.128 (3)	0.0549 (18)	0.082 (2)	0.0388 (18)	0.064 (2)	0.0194 (15)
N1	0.074 (6)	0.047 (5)	0.056 (5)	0.011 (4)	0.040 (5)	0.007 (4)
N2	0.101 (7)	0.032 (5)	0.069 (6)	−0.004 (5)	0.053 (6)	−0.001 (4)
N3	0.077 (6)	0.044 (5)	0.053 (5)	−0.005 (5)	0.034 (5)	0.001 (4)
C1	0.055 (7)	0.037 (6)	0.074 (8)	−0.001 (5)	0.033 (6)	0.004 (5)
C2	0.074 (8)	0.053 (7)	0.063 (8)	−0.006 (6)	0.040 (7)	−0.003 (6)
C3	0.062 (8)	0.065 (8)	0.090 (9)	0.016 (6)	0.046 (7)	0.006 (6)
C4	0.103 (11)	0.054 (8)	0.114 (11)	0.028 (7)	0.065 (10)	0.005 (7)
C5	0.096 (10)	0.082 (9)	0.100 (11)	0.004 (9)	0.067 (9)	−0.011 (8)
C6	0.095 (11)	0.077 (9)	0.078 (9)	−0.003 (8)	0.036 (8)	−0.023 (7)
C7	0.079 (8)	0.065 (8)	0.087 (9)	0.005 (7)	0.047 (8)	−0.006 (7)
C8	0.075 (8)	0.046 (6)	0.055 (7)	0.010 (6)	0.031 (6)	0.013 (5)
C9	0.076 (8)	0.051 (7)	0.069 (8)	−0.005 (6)	0.034 (7)	−0.006 (6)
C10	0.097 (10)	0.070 (8)	0.067 (8)	0.007 (8)	0.039 (8)	−0.011 (6)
C11	0.092 (9)	0.063 (8)	0.086 (9)	0.014 (7)	0.061 (8)	0.009 (7)
C12	0.066 (7)	0.067 (8)	0.083 (8)	0.001 (6)	0.047 (7)	−0.002 (7)
C13	0.076 (8)	0.052 (7)	0.068 (7)	−0.016 (6)	0.036 (7)	−0.002 (6)
C14	0.064 (8)	0.037 (6)	0.069 (8)	0.009 (5)	0.039 (7)	0.003 (5)
C15	0.081 (9)	0.078 (9)	0.080 (9)	0.013 (8)	0.047 (8)	0.003 (7)
C16	0.055 (8)	0.072 (9)	0.100 (11)	−0.001 (7)	0.031 (8)	−0.014 (8)
C17	0.109 (12)	0.110 (13)	0.056 (8)	0.042 (11)	0.025 (9)	−0.004 (9)
C18	0.112 (11)	0.069 (9)	0.059 (9)	−0.006 (9)	0.022 (8)	0.004 (7)
C19	0.079 (8)	0.050 (7)	0.062 (8)	0.000 (6)	0.030 (7)	0.003 (6)

Geometric parameters (Å, º) top

Cu—Cl2	2.263 (3)	C7—H7	0.9300
Cu—Cl2ⁱ	2.263 (3)	C8—C13	1.358 (14)
Cu—Cl1	2.265 (3)	C8—C9	1.400 (14)
Cu—Cl1ⁱ	2.265 (3)	C9—C10	1.372 (15)
N1—C1	1.324 (12)	C9—H9	0.9300
N1—C2	1.404 (12)	C10—C11	1.370 (16)
N1—H1	0.8600	C10—H10	0.9300
N2—C1	1.332 (12)	C11—C12	1.332 (15)
N2—C8	1.433 (12)	C11—H11	0.9300
N2—H2	0.8600	C12—C13	1.351 (14)
N3—C1	1.347 (12)	C12—H12	0.9300
N3—C14	1.411 (12)	C13—H13	0.9300
N3—H3	0.8600	C14—C19	1.355 (14)
C2—C7	1.363 (14)	C14—C15	1.398 (15)
C2—C3	1.379 (14)	C15—C16	1.353 (15)
C3—C4	1.373 (15)	C15—H15	0.9300
C3—H3A	0.9300	C16—C17	1.377 (19)
C4—C5	1.371 (15)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.359 (19)
C5—C6	1.356 (16)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.356 (14)
C6—C7	1.376 (15)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300

Cl2—Cu—Cl2ⁱ	180.00 (15)	C13—C8—C9	119.2 (10)
Cl2—Cu—Cl1	88.65 (10)	C13—C8—N2	122.2 (10)
Cl2ⁱ—Cu—Cl1	91.35 (10)	C9—C8—N2	118.5 (10)
Cl2—Cu—Cl1ⁱ	91.35 (10)	C10—C9—C8	119.1 (11)
Cl2ⁱ—Cu—Cl1ⁱ	88.65 (10)	C10—C9—H9	120.4
Cl1—Cu—Cl1ⁱ	180.00 (16)	C8—C9—H9	120.4
C1—N1—C2	127.0 (9)	C11—C10—C9	119.3 (12)
C1—N1—H1	116.5	C11—C10—H10	120.3
C2—N1—H1	116.5	C9—C10—H10	120.3
C1—N2—C8	126.2 (9)	C12—C11—C10	120.9 (11)
C1—N2—H2	116.9	C12—C11—H11	119.5
C8—N2—H2	116.9	C10—C11—H11	119.5
C1—N3—C14	127.5 (9)	C11—C12—C13	120.9 (11)
C1—N3—H3	116.3	C11—C12—H12	119.5
C14—N3—H3	116.3	C13—C12—H12	119.5
N1—C1—N2	119.6 (9)	C12—C13—C8	120.5 (11)
N1—C1—N3	120.5 (9)	C12—C13—H13	119.8
N2—C1—N3	119.8 (10)	C8—C13—H13	119.8
C7—C2—C3	118.6 (11)	C19—C14—C15	118.3 (11)
C7—C2—N1	118.2 (10)	C19—C14—N3	121.7 (10)
C3—C2—N1	123.2 (10)	C15—C14—N3	120.0 (10)
C4—C3—C2	120.0 (12)	C16—C15—C14	120.7 (12)
C4—C3—H3A	120.0	C16—C15—H15	119.6
C2—C3—H3A	120.0	C14—C15—H15	119.6
C5—C4—C3	120.5 (12)	C15—C16—C17	118.4 (13)
C5—C4—H4	119.8	C15—C16—H16	120.8
C3—C4—H4	119.8	C17—C16—H16	120.8
C6—C5—C4	119.7 (12)	C18—C17—C16	122.1 (13)
C6—C5—H5	120.2	C18—C17—H17	118.9
C4—C5—H5	120.2	C16—C17—H17	118.9
C5—C6—C7	119.8 (12)	C17—C18—C19	118.1 (13)
C5—C6—H6	120.1	C17—C18—H18	120.9
C7—C6—H6	120.1	C19—C18—H18	120.9
C2—C7—C6	121.3 (12)	C14—C19—C18	122.3 (12)
C2—C7—H7	119.4	C14—C19—H19	118.8
C6—C7—H7	119.4	C18—C19—H19	118.8

C2—N1—C1—N2	161.5 (10)	C13—C8—C9—C10	1.8 (16)
C2—N1—C1—N3	−17.6 (16)	N2—C8—C9—C10	179.7 (9)
C8—N2—C1—N1	152.7 (10)	C8—C9—C10—C11	0.1 (17)
C8—N2—C1—N3	−28.2 (16)	C9—C10—C11—C12	−0.9 (17)
C14—N3—C1—N1	146.9 (9)	C10—C11—C12—C13	−0.1 (18)
C14—N3—C1—N2	−32.2 (15)	C11—C12—C13—C8	2.1 (17)
C1—N1—C2—C7	141.5 (11)	C9—C8—C13—C12	−2.9 (16)
C1—N1—C2—C3	−39.4 (16)	N2—C8—C13—C12	179.3 (10)
C7—C2—C3—C4	2.3 (17)	C1—N3—C14—C19	141.6 (11)
N1—C2—C3—C4	−176.8 (10)	C1—N3—C14—C15	−41.1 (15)
C2—C3—C4—C5	−1.4 (19)	C19—C14—C15—C16	−1.8 (16)
C3—C4—C5—C6	1 (2)	N3—C14—C15—C16	−179.2 (9)
C4—C5—C6—C7	−2 (2)	C14—C15—C16—C17	2.9 (17)
C3—C2—C7—C6	−3.2 (17)	C15—C16—C17—C18	−2.4 (19)
N1—C2—C7—C6	175.9 (10)	C16—C17—C18—C19	1 (2)
C5—C6—C7—C2	3.1 (19)	C15—C14—C19—C18	0.1 (16)
C1—N2—C8—C13	−41.0 (15)	N3—C14—C19—C18	177.5 (10)
C1—N2—C8—C9	141.1 (11)	C17—C18—C19—C14	0.4 (18)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱⁱ	0.86	2.28	3.126 (8)	167
N2—H2···Cl1ⁱⁱⁱ	0.86	2.51	3.218 (8)	140
N3—H3···Cl1	0.86	2.44	3.253 (9)	159

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

Experimental details

Crystal data
Chemical formula	(C₁₉H₁₈N₃)₂[CuCl₄]
M_r	782.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.5893 (13), 8.2404 (9), 22.364 (2)
β (°)	119.423 (7)
V (Å³)	1860.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.21 × 0.10 × 0.04

Data collection
Diffractometer	Bruker APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.744, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	27709, 3304, 1405
R_int	0.164
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.097, 0.319, 1.05
No. of reflections	3304
No. of parameters	223
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.29, −0.52

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2ⁱ	0.86	2.28	3.126 (8)	167.3
N2—H2···Cl1ⁱⁱ	0.86	2.51	3.218 (8)	140.1
N3—H3···Cl1	0.86	2.44	3.253 (9)	158.5

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

Acknowledgements

This work was supported by Fundação para a Ciência e a Tecnologia (FCT) under project POCI/FIS/57876/2004.

References

Bian, G.-Q., Kuroda-Sowa, T., Gunjima, N., Maekawa, M. & Munakata, M. (2005). Inorg. Chem. Commun. 8, 208–211. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kemme, A., Rutkis, M. & Eiduss, J. (1988). Latv. PSR Zinat. Akad. Vestis Kim. Ser. 5, 595–601 Google Scholar
Klement, U., Range, K.-J., Hayessen, R. & Heckmann, K.-D. (1995). Z. Kristallogr. 220, 611. CrossRef Google Scholar
Pereira Silva, P. S., Cardoso, C., Ramos Silva, M. & Paixão, J. A. (2007). Acta Cryst. E63, o501–o503. Web of Science CSD CrossRef IUCr Journals Google Scholar
Pereira Silva, P. S., Paixão, J. A., Ramos Silva, M. & Matos Beja, A. (2006). Acta Cryst. E62, o3073–o3075. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar