(1-{2-[2-(2-Ammonio­ethyl­amino)ethyl­amino]ethyl­imino­meth­yl}-2-naphtholato-κ4O,N,N′,N′′)chloridocopper(II) chloride

Xue, R.; Niu, M.

doi:10.1107/S1600536807064033

metal-organic compounds

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Volume 64| Part 1| January 2008| Page m118

https://doi.org/10.1107/S1600536807064033

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(1-{2-[2-(2-Ammonioethylamino)ethylamino]ethyliminomethyl}-2-naphtholato-κ⁴O,N,N′,N′′)chloridocopper(II) chloride

Ruiting Xue ^a and Meiju Niu ^a ^*

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: niumeiju@163.com

(Received 17 November 2007; accepted 28 November 2007; online 6 December 2007)

In the square-pyramidal title complex, [CuCl(C₁₇H₂₄N₄O)]Cl, the Cu^II atom is coordinated by three N atoms [Cu—N 1.946 (2), 2.010 (2), 2.085 (3) Å], one O atom [Cu—O 1.910 (2) Å] and one apical Cl atom [Cu—Cl 2.6437 (9) Å]. The three coordinated N and one O atom are almost coplanar, with a maximum deviation of 0.0268 Å. The tetradentate ligand forms two five-membered (N—Cu—N) and one six-membered (N—Cu—O) chelate rings with bite angles of 84.06 (10), 85.30 (10) and 91.70 (9)°, respectively. The two N—Cu—N chelate rings are non-planar.

Related literature

For the general role of Schiff bases, see: Gamovski et al. (1993 ). For the crystal structures of related complexes, see: Nanda et al. (2006 ).

Experimental

Crystal data

[CuCl(C₁₇H₂₄N₄O)]Cl
M_r = 434.84
Monoclinic, P 2₁ /c
a = 12.2687 (17) Å
b = 13.0277 (18) Å
c = 12.7118 (18) Å
β = 111.365 (2)°
V = 1892.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.45 mm⁻¹
T = 298 (2) K
0.48 × 0.40 × 0.37 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.543, T_max = 0.616 (expected range = 0.515–0.585)
9597 measured reflections
3320 independent reflections
2646 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.099
S = 1.00
3320 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl2ⁱ	0.91	2.44	3.225 (3)	144
N3—H3⋯Cl1ⁱⁱ	0.91	2.50	3.388 (3)	165
N4—H4A⋯Cl1ⁱⁱⁱ	0.89	2.31	3.204 (3)	177
N4—H4B⋯Cl2ⁱⁱ	0.89	2.25	3.079 (4)	156
N4—H4C⋯O1	0.89	1.83	2.703 (4)	167
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807064033/ln2007sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064033/ln2007Isup2.hkl

checkCIF report

Comment top

Schiff base complexes play an important role in coordination chemistry (Gamovski et al., 1993). In a continuation of a study of Schiff base ligands and their copper(II) complexes, we report here the title complex (Fig. 1), in which the ligand donor atoms consist of three nitrogen atoms (one imine and two amine) and one phenolic oxygen atom. Another Cu^II complex containing the same tetradentate ligand has been reported by Nanda et al. (2006). In the crystal structure of (I), intermolecular N—H···Cl hydrogen bonds involving all amine and the ammonium groups link the molecules into two-dimensional networks, which lie parallel to the (100) plane (Table 1, Fig. 2). The ammonium group also forms an intramolecular hydrogen bond with the phenolic O atom.

Related literature top

For the general role of Schiff bases, see: Gamovski et al. (1993). For thecrystal structures of related complexes, see: Nanda et al. (2006).

Experimental top

A solution of triethylenetetramine(1 mmol) in hot methanol (10 ml) was added dropwise to a methanol solution (5 ml) of 2-hydroxy-1-naphthaldehyde (2 mmol, 344.3 mg). The mixture was then stirred at 323 K for 2 h. An aqueous solution (2 ml) of cupric chloride dihydrate (1 mmol, 170.8 mg) was then added dropwise and the mixture stirred for another 5 h. The solution was held at room temperature for about one week, whereupon green prism-shaped crystals suitable for X-ray diffraction analysis were obtained (m.p. > 573 K).

Structure description top

For the general role of Schiff bases, see: Gamovski et al. (1993). For thecrystal structures of related complexes, see: Nanda et al. (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Crystal packing of the title complex showing the hydrogen bonding interactions as dashed lines.

(1-{2-[2-(2-Ammonioethylamino)ethylamino]ethyliminomethyl}-2-naphtholato- κ⁴O,N,N',N'')chloridocopper(II) chloride top

Crystal data top

[CuCl(C₁₇H₂₄N₄O)]Cl	F(000) = 900
M_r = 434.84	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.2687 (17) Å	Cell parameters from 3813 reflections
b = 13.0277 (18) Å	θ = 2.5–26.7°
c = 12.7118 (18) Å	µ = 1.45 mm⁻¹
β = 111.365 (2)°	T = 298 K
V = 1892.1 (5) Å³	Block, green
Z = 4	0.48 × 0.40 × 0.37 mm

Data collection top

Bruker CCD area-detector diffractometer	3320 independent reflections
Radiation source: fine-focus sealed tube	2646 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.543, T_max = 0.616	k = −15→12
9597 measured reflections	l = −14→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0538P)² + 1.3872P] where P = (F_o² + 2F_c²)/3
3320 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[CuCl(C₁₇H₂₄N₄O)]Cl	V = 1892.1 (5) Å³
M_r = 434.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.2687 (17) Å	µ = 1.45 mm⁻¹
b = 13.0277 (18) Å	T = 298 K
c = 12.7118 (18) Å	0.48 × 0.40 × 0.37 mm
β = 111.365 (2)°

Data collection top

Bruker CCD area-detector diffractometer	3320 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2646 reflections with I > 2σ(I)
T_min = 0.543, T_max = 0.616	R_int = 0.027
9597 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.59 e Å⁻³
3320 reflections	Δρ_min = −0.40 e Å⁻³
226 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
Cu1	0.70712 (3)	0.22917 (3)	0.92710 (3)	0.03282 (14)
Cl1	0.59641 (8)	0.15391 (7)	0.72264 (7)	0.0511 (2)
Cl2	0.26659 (9)	0.14202 (8)	0.07523 (10)	0.0662 (3)
N1	0.8689 (2)	0.22822 (18)	0.9363 (2)	0.0327 (6)
N2	0.7491 (2)	0.09353 (18)	1.0070 (2)	0.0342 (6)
H2	0.7261	0.0426	0.9545	0.041*
N3	0.5626 (2)	0.22573 (19)	0.9765 (2)	0.0377 (6)
H3	0.5809	0.2667	1.0385	0.045*
N4	0.4596 (3)	0.4130 (2)	0.8025 (3)	0.0599 (8)
H4A	0.4462	0.4803	0.7985	0.090*
H4B	0.4206	0.3844	0.7358	0.090*
H4C	0.5359	0.4017	0.8212	0.090*
O1	0.69138 (17)	0.37176 (15)	0.88974 (19)	0.0406 (5)
C1	0.9272 (3)	0.3033 (2)	0.9185 (2)	0.0328 (7)
H1	1.0057	0.2918	0.9308	0.039*
C2	0.8815 (2)	0.4046 (2)	0.8810 (2)	0.0304 (6)
C3	0.7695 (3)	0.4344 (2)	0.8753 (2)	0.0328 (7)
C4	0.7349 (3)	0.5390 (2)	0.8524 (3)	0.0400 (7)
H4	0.6622	0.5597	0.8519	0.048*
C5	0.8061 (3)	0.6090 (2)	0.8313 (3)	0.0418 (8)
H5	0.7816	0.6769	0.8181	0.050*
C6	0.9163 (3)	0.5815 (2)	0.8290 (3)	0.0372 (7)
C7	0.9567 (3)	0.4795 (2)	0.8561 (2)	0.0332 (7)
C8	1.0697 (3)	0.4563 (2)	0.8560 (3)	0.0438 (8)
H8	1.0987	0.3900	0.8728	0.053*
C9	1.1367 (3)	0.5298 (3)	0.8319 (3)	0.0502 (9)
H9	1.2108	0.5127	0.8333	0.060*
C10	1.0955 (3)	0.6301 (3)	0.8050 (3)	0.0499 (9)
H10	1.1418	0.6794	0.7887	0.060*
C11	0.9881 (3)	0.6547 (3)	0.8030 (3)	0.0471 (8)
H11	0.9605	0.7213	0.7842	0.057*
C12	0.9279 (3)	0.1298 (2)	0.9797 (3)	0.0411 (8)
H12A	1.0116	0.1403	1.0163	0.049*
H12B	0.9145	0.0815	0.9182	0.049*
C13	0.8775 (3)	0.0893 (2)	1.0628 (3)	0.0395 (7)
H13A	0.9029	0.0192	1.0836	0.047*
H13B	0.9029	0.1310	1.1307	0.047*
C14	0.6823 (3)	0.0837 (3)	1.0821 (3)	0.0460 (8)
H14A	0.7172	0.1258	1.1490	0.055*
H14B	0.6820	0.0129	1.1055	0.055*
C15	0.5603 (3)	0.1189 (2)	1.0168 (3)	0.0470 (8)
H15A	0.5244	0.0738	0.9527	0.056*
H15B	0.5140	0.1163	1.0644	0.056*
C16	0.4418 (3)	0.2538 (3)	0.9023 (4)	0.0547 (10)
H16A	0.3873	0.2243	0.9333	0.066*
H16B	0.4255	0.2236	0.8284	0.066*
C17	0.4203 (4)	0.3678 (3)	0.8885 (4)	0.0680 (12)
H17A	0.3373	0.3808	0.8678	0.082*
H17B	0.4609	0.4012	0.9604	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0285 (2)	0.0288 (2)	0.0378 (2)	0.00173 (14)	0.00819 (16)	0.00456 (15)
Cl1	0.0517 (5)	0.0531 (5)	0.0416 (5)	−0.0067 (4)	0.0088 (4)	−0.0052 (4)
Cl2	0.0524 (6)	0.0529 (6)	0.0853 (7)	0.0006 (4)	0.0156 (5)	−0.0208 (5)
N1	0.0287 (13)	0.0297 (13)	0.0362 (14)	0.0036 (10)	0.0075 (11)	0.0021 (11)
N2	0.0332 (14)	0.0299 (13)	0.0334 (14)	−0.0002 (10)	0.0048 (11)	0.0015 (11)
N3	0.0373 (14)	0.0330 (14)	0.0456 (16)	−0.0008 (11)	0.0183 (12)	0.0041 (11)
N4	0.0419 (17)	0.0528 (19)	0.077 (2)	0.0075 (14)	0.0127 (16)	0.0175 (17)
O1	0.0283 (11)	0.0320 (12)	0.0581 (14)	0.0030 (9)	0.0117 (10)	0.0069 (10)
C1	0.0287 (15)	0.0347 (16)	0.0330 (16)	0.0019 (12)	0.0087 (13)	−0.0028 (13)
C2	0.0323 (15)	0.0295 (15)	0.0249 (15)	−0.0011 (12)	0.0050 (12)	−0.0033 (12)
C3	0.0349 (16)	0.0288 (15)	0.0304 (16)	−0.0018 (13)	0.0066 (13)	−0.0024 (12)
C4	0.0362 (17)	0.0326 (17)	0.047 (2)	0.0045 (13)	0.0108 (15)	0.0005 (14)
C5	0.048 (2)	0.0275 (16)	0.0448 (19)	0.0033 (14)	0.0114 (16)	0.0015 (14)
C6	0.0415 (18)	0.0325 (16)	0.0332 (17)	−0.0052 (13)	0.0083 (14)	−0.0007 (13)
C7	0.0345 (16)	0.0344 (16)	0.0258 (15)	−0.0035 (13)	0.0051 (13)	−0.0055 (12)
C8	0.0436 (19)	0.0414 (19)	0.047 (2)	−0.0032 (15)	0.0172 (16)	0.0012 (15)
C9	0.042 (2)	0.057 (2)	0.054 (2)	−0.0056 (16)	0.0204 (17)	0.0024 (17)
C10	0.053 (2)	0.051 (2)	0.047 (2)	−0.0159 (17)	0.0193 (18)	0.0033 (16)
C11	0.058 (2)	0.0377 (18)	0.0417 (19)	−0.0077 (16)	0.0135 (17)	0.0023 (15)
C12	0.0310 (17)	0.0336 (17)	0.054 (2)	0.0074 (13)	0.0098 (15)	0.0043 (14)
C13	0.0352 (17)	0.0320 (17)	0.0422 (18)	0.0044 (13)	0.0032 (14)	0.0063 (13)
C14	0.048 (2)	0.0414 (19)	0.049 (2)	0.0008 (15)	0.0181 (17)	0.0124 (16)
C15	0.047 (2)	0.0382 (18)	0.060 (2)	−0.0022 (15)	0.0240 (18)	0.0106 (16)
C16	0.0349 (19)	0.059 (2)	0.070 (3)	0.0065 (16)	0.0185 (18)	0.0179 (19)
C17	0.061 (3)	0.067 (3)	0.083 (3)	0.026 (2)	0.035 (2)	0.021 (2)

Geometric parameters (Å, º) top

Cu1—O1	1.910 (2)	C5—H5	0.9300
Cu1—N1	1.946 (2)	C6—C7	1.415 (4)
Cu1—N2	2.010 (2)	C6—C11	1.417 (4)
Cu1—N3	2.085 (3)	C7—C8	1.420 (4)
Cu1—Cl1	2.6437 (9)	C8—C9	1.367 (5)
N1—C1	1.280 (4)	C8—H8	0.9300
N1—C12	1.477 (4)	C9—C10	1.398 (5)
N2—C14	1.472 (4)	C9—H9	0.9300
N2—C13	1.475 (4)	C10—C11	1.347 (5)
N2—H2	0.9100	C10—H10	0.9300
N3—C16	1.484 (4)	C11—H11	0.9300
N3—C15	1.487 (4)	C12—C13	1.502 (5)
N3—H3	0.9100	C12—H12A	0.9700
N4—C17	1.470 (5)	C12—H12B	0.9700
N4—H4A	0.8900	C13—H13A	0.9700
N4—H4B	0.8900	C13—H13B	0.9700
N4—H4C	0.8900	C14—C15	1.495 (5)
O1—C3	1.321 (3)	C14—H14A	0.9700
C1—C2	1.445 (4)	C14—H14B	0.9700
C1—H1	0.9300	C15—H15A	0.9700
C2—C3	1.404 (4)	C15—H15B	0.9700
C2—C7	1.455 (4)	C16—C17	1.507 (5)
C3—C4	1.426 (4)	C16—H16A	0.9700
C4—C5	1.355 (4)	C16—H16B	0.9700
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.410 (4)	C17—H17B	0.9700

O1—Cu1—N1	91.70 (9)	C6—C7—C2	119.3 (3)
O1—Cu1—N2	164.83 (10)	C8—C7—C2	123.6 (3)
N1—Cu1—N2	84.06 (10)	C9—C8—C7	121.2 (3)
O1—Cu1—N3	94.34 (9)	C9—C8—H8	119.4
N1—Cu1—N3	160.46 (11)	C7—C8—H8	119.4
N2—Cu1—N3	85.30 (10)	C8—C9—C10	121.0 (3)
O1—Cu1—Cl1	98.46 (7)	C8—C9—H9	119.5
N1—Cu1—Cl1	101.77 (8)	C10—C9—H9	119.5
N2—Cu1—Cl1	96.66 (7)	C11—C10—C9	119.5 (3)
N3—Cu1—Cl1	95.70 (8)	C11—C10—H10	120.3
C1—N1—C12	120.0 (3)	C9—C10—H10	120.3
C1—N1—Cu1	127.5 (2)	C10—C11—C6	121.4 (3)
C12—N1—Cu1	112.23 (19)	C10—C11—H11	119.3
C14—N2—C13	115.7 (2)	C6—C11—H11	119.3
C14—N2—Cu1	107.68 (18)	N1—C12—C13	107.3 (2)
C13—N2—Cu1	107.95 (18)	N1—C12—H12A	110.3
C14—N2—H2	108.4	C13—C12—H12A	110.3
C13—N2—H2	108.4	N1—C12—H12B	110.3
Cu1—N2—H2	108.4	C13—C12—H12B	110.3
C16—N3—C15	108.0 (2)	H12A—C12—H12B	108.5
C16—N3—Cu1	124.5 (2)	N2—C13—C12	106.9 (2)
C15—N3—Cu1	104.42 (18)	N2—C13—H13A	110.4
C16—N3—H3	106.3	C12—C13—H13A	110.4
C15—N3—H3	106.3	N2—C13—H13B	110.4
Cu1—N3—H3	106.3	C12—C13—H13B	110.4
C17—N4—H4A	109.5	H13A—C13—H13B	108.6
C17—N4—H4B	109.5	N2—C14—C15	107.1 (3)
H4A—N4—H4B	109.5	N2—C14—H14A	110.3
C17—N4—H4C	109.5	C15—C14—H14A	110.3
H4A—N4—H4C	109.5	N2—C14—H14B	110.3
H4B—N4—H4C	109.5	C15—C14—H14B	110.3
C3—O1—Cu1	128.49 (18)	H14A—C14—H14B	108.6
N1—C1—C2	125.5 (3)	N3—C15—C14	109.7 (3)
N1—C1—H1	117.2	N3—C15—H15A	109.7
C2—C1—H1	117.2	C14—C15—H15A	109.7
C3—C2—C1	121.6 (3)	N3—C15—H15B	109.7
C3—C2—C7	119.3 (3)	C14—C15—H15B	109.7
C1—C2—C7	118.9 (3)	H15A—C15—H15B	108.2
O1—C3—C2	124.6 (3)	N3—C16—C17	114.1 (3)
O1—C3—C4	116.2 (3)	N3—C16—H16A	108.7
C2—C3—C4	119.2 (3)	C17—C16—H16A	108.7
C5—C4—C3	121.2 (3)	N3—C16—H16B	108.7
C5—C4—H4	119.4	C17—C16—H16B	108.7
C3—C4—H4	119.4	H16A—C16—H16B	107.6
C4—C5—C6	121.7 (3)	N4—C17—C16	113.0 (3)
C4—C5—H5	119.1	N4—C17—H17A	109.0
C6—C5—H5	119.1	C16—C17—H17A	109.0
C5—C6—C7	119.1 (3)	N4—C17—H17B	109.0
C5—C6—C11	121.1 (3)	C16—C17—H17B	109.0
C7—C6—C11	119.8 (3)	H17A—C17—H17B	107.8
C6—C7—C8	117.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl2ⁱ	0.91	2.44	3.225 (3)	144
N3—H3···Cl1ⁱⁱ	0.91	2.50	3.388 (3)	165
N4—H4A···Cl1ⁱⁱⁱ	0.89	2.31	3.204 (3)	177
N4—H4B···Cl2ⁱⁱ	0.89	2.25	3.079 (4)	156
N4—H4C···O1	0.89	1.83	2.703 (4)	167

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[CuCl(C₁₇H₂₄N₄O)]Cl
M_r	434.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.2687 (17), 13.0277 (18), 12.7118 (18)
β (°)	111.365 (2)
V (Å³)	1892.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.45
Crystal size (mm)	0.48 × 0.40 × 0.37

Data collection
Diffractometer	Bruker CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.543, 0.616
No. of measured, independent and observed [I > 2σ(I)] reflections	9597, 3320, 2646
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.099, 1.00
No. of reflections	3320
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.40

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl2ⁱ	0.91	2.44	3.225 (3)	144
N3—H3···Cl1ⁱⁱ	0.91	2.50	3.388 (3)	165
N4—H4A···Cl1ⁱⁱⁱ	0.89	2.31	3.204 (3)	177
N4—H4B···Cl2ⁱⁱ	0.89	2.25	3.079 (4)	156
N4—H4C···O1	0.89	1.83	2.703 (4)	167

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors acknowledge the financial support of the Shandong Province Science Foundation and the State Key Laboratory of Crystalline Materials, Shandong University, People's Republic of China.

References

Gamovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69. CrossRef Web of Science Google Scholar
Nanda, P. K., Bera, M., Aromi, G. & Ray, D. (2006). Polyhedron, 25, 2791–2799. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instrument Inc., Madison, Wisconsin, USA. Google Scholar

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