Dichloridobis[2-(2-chloro­ethyl)-1,2,3,4-tetra­hydro­pyrazino[1,2-a]benzimidazole-κN]cobalt(II)

Zhang, Z.; Zhao, Y.; Geng, Z.-R.; Wang, Z.-L.

doi:10.1107/S1600536808018011

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages m942-m943

doi:10.1107/S1600536808018011

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Dichloridobis[2-(2-chloroethyl)-1,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole-κN]cobalt(II)

Zhong Zhang,^a Yao Zhao,^a Zhi-Rong Geng ^a and Zhi-Lin Wang ^a ^*

^aCoordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: zzkltl@163.com

(Received 10 May 2008; accepted 13 June 2008; online 19 June 2008)

In the title compound, [CoCl₂(C₁₂H₁₄ClN₃)₂], the central Co^II ion lies on a twofold rotation axis and adopts a distorted tetrahedral coordination geometry defined by two N atoms from two 2-(2-chloroethyl)-1,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole ligands and two chloride anions. The Cl atom located in the side chain of the ligand is involved in intermolecular C—H⋯Cl hydrogen bonding, which links neutral complex units into a one-dimensional right-handed helical chain running along a crystallographic 4₁ axis. Such hydrogen-bonded helical chains are connected to each other to form a homochiral three-dimensional supramolecular network. One C atom of the 2-chloroethyl chain is disordered over two positions, with site-occupancy factors of 0.52 and 0.48.

Related literature

For related literature, see: Balamurugan et al. (2004 ); Matrick & Day (1961 ); Parker et al. (2004 ); Sundberg et al. (1977 ).

Experimental

Crystal data

[CoCl₂(C₁₂H₁₄ClN₃)₂]
M_r = 601.25
Tetragonal, P 4₁ 2₁ 2
a = 9.5706 (8) Å
c = 29.911 (4) Å
V = 2739.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 293 (2) K
0.32 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.763, T_max = 0.829
14573 measured reflections
2703 independent reflections
2219 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.131
S = 1.01
2703 reflections
169 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.80 e Å⁻³
Absolute structure: Flack (1983 ), 1274 Friedel pairs
Flack parameter: 0.07 (5)

Table 1
Selected geometric parameters (Å, °)

Co1—N2	2.026 (4)
Co1—Cl2	2.2423 (13)

N2ⁱ—Co1—N2	103.8 (2)
N2—Co1—Cl2	109.08 (12)
Cl2—Co1—Cl2ⁱ	110.64 (7)
Symmetry code: (i) y, x, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl1ⁱⁱ	0.97	2.87	3.812 (5)	164
C5—H5⋯Cl2ⁱⁱⁱ	0.93	2.79	3.709 (5)	171
Symmetry codes: (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 4}}]$ ; (iii) $[y-{\script{1\over 2}}, -x+{\script{5\over 2}}, z-{\script{1\over 4}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1998 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018011/om2235sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018011/om2235Isup2.hkl

checkCIF report

Comment top

Nitrogen mustards that contain a reactive N,N-bis-(2-chloroethyl)amine group are widely used as alkylating agents in cancer chemotherapy. However, these nitrogen mustards exhibit high chemical reactivity and usually show no selectivity of DNA alkylation. Recently, it has been proved that complexation of macrocyclic nitrogen mustards with metals may be an effective strategy in the design of hypoxia-selective antitumor prodrugs (Parker et al., 2004). As part of our work, some metal complexes of a monofunctional mustard, 2-(2-chloroethyl)-l,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole (L), were prepared in order to evaluate their antitumor and antimalarial activities. Here, we report the crystal structure of a novel Co(II) mustard complex.

As depicted in Fig. 1, the complete complex molecule is generated by a twofold symmetry operation, with the Co^II ion located on the rotation axis. The distorted tetrahedral coordination sphere around the Co^II center consists of two benzimidazole N atoms from two L ligands and two chloride anions. The Co—N distance of 2.026 (4) Å and Co—Cl length of 2.2423 (13) Å (Table 1) are comparable to those reported in the literature (Sundberg et al., 1977).

In the crystal packing, intermolecular C—H···Cl hydrogen bonding play a key role. Fig. 2 illustrates that adjacent neutral complex units are connected by C1—H1A···Cl1 interactions into a one-dimensional right-handed helical architecture running along a crystallographic 4₁ screw axis in the c direction. Five complex fragments form a helix turn with a long pitch of 29.911 (4) Å. The shortest intrachain Co—Co distance is 10.072 Å. Further C—H···Cl hydrogen bond linkages (Table 2) extend such one-dimensional helical chains into a homochiral three-dimensional hydrogen-bonded network (Balamurugan et al., 2004).

Related literature top

For related literature, see: Balamurugan et al. (2004); Matrick & Day (1961); Parker et al. (2004); Sundberg et al. (1977).

Experimental top

The ligand 2-(2-chloroethyl)-l,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole was synthesized according to a literature method (Matrick & Day, 1961).

The title compound was prepared by adding a methanol solution (10 ml) of CoCl₂.6H₂O (1 mmol) into a methanol solution (10 ml) of 2-(2-chloroethyl)-l,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole (2 mmol). The resulting mixture was refluxed for two hours and filtered after cooling to room temperature. Blue single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow diffusion of diethyl ether into the filtrate. Elemental analysis found: C 47.80; H 4.60; N 14.03%; calculated for C₂₄H₂₈Cl₄CoN₆: C 47.94; H 4.69; N 13.98%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1998) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure with atom labels and 30% probability displacement ellipsoids for non-H atoms. Both disordered components of the 2-chloroethyl chain are shown. [Symmetry code: (i) y, x, -z]
	Fig. 2. Fragment of a one-dimensional right-handed helical chain with the intermolecular C—H···Cl hydrogen bond indicated by dashed line. For clarity only the major disordered component is shown. [Symmetry code: (ii) 3/2 - x, -1/2 + y, 1/4 - z]

dichloridobis[2-(2-chloroethyl)-1,2,3,4- tetrahydropyrazino[1,2-a]benzimidazole-κN]cobalt(II) top

Crystal data top

[CoCl₂(C₁₂H₁₄ClN₃)₂]	D_x = 1.458 Mg m⁻³
M_r = 601.25	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 835 reflections
Hall symbol: P 4abw 2nw	θ = 2.5–16.9°
a = 9.5706 (8) Å	µ = 1.04 mm⁻¹
c = 29.911 (4) Å	T = 293 K
V = 2739.7 (5) Å³	Prism, blue
Z = 4	0.32 × 0.21 × 0.18 mm
F(000) = 1236

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2703 independent reflections
Radiation source: sealed tube	2219 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→7
T_min = 0.763, T_max = 0.829	k = −11→11
14573 measured reflections	l = −36→35

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)] = 0.055	H-atom parameters constrained
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0877P)² + 1.82P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2703 reflections	Δρ_max = 0.54 e Å⁻³
169 parameters	Δρ_min = −0.80 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1274 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (5)

Crystal data top

[CoCl₂(C₁₂H₁₄ClN₃)₂]	Z = 4
M_r = 601.25	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 1.04 mm⁻¹
a = 9.5706 (8) Å	T = 293 K
c = 29.911 (4) Å	0.32 × 0.21 × 0.18 mm
V = 2739.7 (5) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2703 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2219 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.829	R_int = 0.061
14573 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.131	Δρ_max = 0.54 e Å⁻³
S = 1.01	Δρ_min = −0.80 e Å⁻³
2703 reflections	Absolute structure: Flack (1983), 1274 Friedel pairs
169 parameters	Absolute structure parameter: 0.07 (5)
2 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	Occ. (<1)
Co1	0.99857 (7)	0.99857 (7)	0.0000	0.0305 (2)
C1	0.7722 (5)	0.8869 (5)	0.07778 (15)	0.0312 (10)
H1A	0.7825	0.7909	0.0679	0.037*
H1B	0.8635	0.9211	0.0866	0.037*
C2	0.7177 (5)	0.9724 (5)	0.04111 (16)	0.0327 (11)
C3	0.6905 (5)	1.0950 (5)	−0.01903 (17)	0.0336 (11)
C4	0.7080 (5)	1.1677 (5)	−0.05859 (18)	0.0332 (11)
H4	0.7945	1.1750	−0.0726	0.040*
C5	0.5873 (5)	1.2300 (5)	−0.07639 (16)	0.0339 (11)
H5	0.5940	1.2775	−0.1034	0.041*
C6	0.4595 (6)	1.2234 (5)	−0.05550 (17)	0.0368 (12)
H6	0.3826	1.2693	−0.0675	0.044*
C7	0.4469 (5)	1.1478 (5)	−0.01639 (16)	0.0317 (11)
H7	0.3604	1.1398	−0.0024	0.038*
C8	0.5617 (5)	1.0847 (5)	0.00170 (18)	0.0335 (11)
C9	0.4822 (5)	0.9696 (5)	0.07306 (16)	0.0325 (11)
H9A	0.3964	0.9399	0.0587	0.039*
H9B	0.4612	1.0496	0.0918	0.039*
C10	0.5382 (5)	0.8555 (5)	0.10051 (16)	0.0354 (12)
H10A	0.4780	0.8397	0.1261	0.042*
H10B	0.5418	0.7701	0.0831	0.042*
C11	0.7325 (6)	0.8092 (5)	0.15130 (16)	0.0348 (11)
H11A	0.7724	0.7247	0.1387	0.042*	0.520 (13)
H11B	0.6558	0.7816	0.1706	0.042*	0.520 (13)
H11C	0.8335	0.8174	0.1515	0.042*	0.480 (13)
H11D	0.7095	0.7120	0.1458	0.042*	0.480 (13)
C12A	0.8428 (10)	0.8809 (9)	0.1796 (3)	0.033 (3)	0.520 (13)
H12A	0.9132	0.9212	0.1601	0.039*	0.520 (13)
H12B	0.8883	0.8121	0.1984	0.039*	0.520 (13)
C12B	0.6908 (11)	0.8567 (10)	0.1978 (3)	0.034 (3)	0.480 (13)
H12C	0.7154	0.7845	0.2192	0.040*	0.480 (13)
H12D	0.5903	0.8691	0.1988	0.040*	0.480 (13)
N1	0.6779 (4)	0.8924 (5)	0.11560 (13)	0.0345 (9)
N2	0.7894 (4)	1.0231 (4)	0.00683 (13)	0.0341 (9)
N3	0.5833 (4)	1.0082 (5)	0.03979 (13)	0.0359 (9)
Cl1	0.77153 (12)	1.01254 (13)	0.21326 (4)	0.0341 (3)
Cl2	1.10525 (13)	1.08043 (13)	0.06139 (4)	0.0345 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0302 (3)	0.0302 (3)	0.0311 (4)	−0.0010 (4)	0.0031 (3)	−0.0031 (3)
C1	0.033 (3)	0.030 (2)	0.030 (2)	−0.004 (2)	−0.003 (2)	0.001 (2)
C2	0.036 (3)	0.032 (3)	0.031 (2)	0.003 (2)	0.012 (2)	0.005 (2)
C3	0.035 (3)	0.028 (3)	0.038 (3)	0.000 (2)	−0.009 (2)	−0.007 (2)
C4	0.029 (3)	0.032 (3)	0.039 (3)	0.001 (2)	−0.005 (2)	0.007 (2)
C5	0.036 (3)	0.028 (3)	0.037 (3)	−0.006 (2)	−0.002 (2)	0.017 (2)
C6	0.038 (3)	0.032 (3)	0.040 (3)	0.005 (2)	−0.002 (2)	−0.003 (2)
C7	0.032 (3)	0.032 (3)	0.031 (2)	0.005 (2)	0.000 (2)	−0.0074 (19)
C8	0.031 (3)	0.035 (3)	0.035 (2)	0.005 (2)	−0.009 (2)	−0.007 (2)
C9	0.031 (3)	0.035 (3)	0.031 (2)	−0.005 (2)	0.002 (2)	0.0002 (19)
C10	0.036 (3)	0.041 (3)	0.029 (2)	0.001 (2)	0.003 (2)	0.016 (2)
C11	0.040 (3)	0.036 (3)	0.029 (3)	0.002 (2)	−0.002 (2)	−0.003 (2)
C12A	0.036 (5)	0.031 (5)	0.031 (5)	0.000 (4)	−0.002 (4)	0.007 (4)
C12B	0.032 (6)	0.032 (6)	0.036 (6)	0.001 (4)	−0.003 (4)	0.002 (4)
N1	0.039 (2)	0.035 (2)	0.030 (2)	0.0055 (19)	0.0004 (18)	0.0035 (18)
N2	0.035 (2)	0.037 (2)	0.0303 (19)	0.0010 (18)	−0.0003 (17)	−0.0028 (17)
N3	0.036 (2)	0.035 (2)	0.037 (2)	−0.0003 (19)	0.0060 (18)	0.005 (2)
Cl1	0.0330 (6)	0.0355 (6)	0.0339 (6)	−0.0082 (5)	−0.0012 (5)	−0.0007 (5)
Cl2	0.0367 (7)	0.0333 (7)	0.0336 (6)	−0.0011 (5)	−0.0071 (5)	−0.0038 (5)

Geometric parameters (Å, º) top

Co1—N2ⁱ	2.026 (4)	C9—N3	1.436 (6)
Co1—N2	2.026 (4)	C9—C10	1.468 (6)
Co1—Cl2	2.2423 (13)	C9—H9A	0.9700
Co1—Cl2ⁱ	2.2423 (13)	C9—H9B	0.9700
C1—N1	1.448 (6)	C10—N1	1.454 (7)
C1—C2	1.465 (6)	C10—H10A	0.9700
C1—H1A	0.9700	C10—H10B	0.9700
C1—H1B	0.9700	C11—N1	1.431 (6)
C2—N2	1.325 (6)	C11—C12A	1.517 (10)
C2—N3	1.332 (6)	C11—C12B	1.517 (10)
C3—C4	1.383 (7)	C11—H11A	0.9700
C3—C8	1.383 (7)	C11—H11B	0.9700
C3—N2	1.403 (6)	C11—H11C	0.9700
C4—C5	1.405 (7)	C11—H11D	0.9700
C4—H4	0.9300	C12A—Cl1	1.752 (9)
C5—C6	1.374 (7)	C12A—H11C	1.0395
C5—H5	0.9300	C12A—H12A	0.9700
C6—C7	1.381 (7)	C12A—H12B	0.9700
C6—H6	0.9300	C12B—Cl1	1.742 (9)
C7—C8	1.366 (7)	C12B—H12C	0.9700
C7—H7	0.9300	C12B—H12D	0.9700
C8—N3	1.370 (7)

N2ⁱ—Co1—N2	103.8 (2)	N1—C10—C9	109.2 (4)
N2ⁱ—Co1—Cl2	112.03 (12)	N1—C10—H10A	109.8
N2—Co1—Cl2	109.08 (12)	C9—C10—H10A	109.8
N2ⁱ—Co1—Cl2ⁱ	109.08 (12)	N1—C10—H10B	109.8
N2—Co1—Cl2ⁱ	112.03 (12)	C9—C10—H10B	109.8
Cl2—Co1—Cl2ⁱ	110.64 (7)	H10A—C10—H10B	108.3
N1—C1—C2	110.0 (4)	N1—C11—C12A	114.8 (5)
N1—C1—H1A	109.7	N1—C11—C12B	114.9 (5)
C2—C1—H1A	109.7	N1—C11—H11A	108.6
N1—C1—H1B	109.7	C12A—C11—H11A	108.6
C2—C1—H1B	109.7	N1—C11—H11B	108.6
H1A—C1—H1B	108.2	C12A—C11—H11B	108.6
N2—C2—N3	112.5 (4)	H11A—C11—H11B	107.6
N2—C2—C1	126.8 (5)	N1—C11—H11C	109.0
N3—C2—C1	120.6 (4)	C12B—C11—H11C	103.4
C4—C3—C8	121.8 (5)	N1—C11—H11D	109.0
C4—C3—N2	129.6 (5)	C12B—C11—H11D	112.5
C8—C3—N2	108.6 (4)	H11C—C11—H11D	107.8
C3—C4—C5	116.0 (5)	C11—C12A—Cl1	112.0 (6)
C3—C4—H4	122.0	C11—C12A—H12A	109.2
C5—C4—H4	122.0	Cl1—C12A—H12A	109.2
C6—C5—C4	122.7 (4)	C11—C12A—H12B	109.2
C6—C5—H5	118.7	Cl1—C12A—H12B	109.2
C4—C5—H5	118.7	H12A—C12A—H12B	107.9
C5—C6—C7	119.2 (5)	C11—C12B—Cl1	112.5 (6)
C5—C6—H6	120.4	C11—C12B—H12C	109.1
C7—C6—H6	120.4	Cl1—C12B—H12C	109.1
C8—C7—C6	119.8 (5)	C11—C12B—H12D	109.1
C8—C7—H7	120.1	Cl1—C12B—H12D	109.1
C6—C7—H7	120.1	H12C—C12B—H12D	107.8
C7—C8—N3	133.4 (5)	C11—N1—C1	109.6 (4)
C7—C8—C3	120.5 (5)	C11—N1—C10	115.6 (4)
N3—C8—C3	106.1 (4)	C1—N1—C10	108.8 (4)
N3—C9—C10	109.4 (4)	C2—N2—C3	104.9 (4)
N3—C9—H9A	109.8	C2—N2—Co1	123.2 (3)
C10—C9—H9A	109.8	C3—N2—Co1	131.9 (3)
N3—C9—H9B	109.8	C2—N3—C8	107.9 (4)
C10—C9—H9B	109.8	C2—N3—C9	124.4 (4)
H9A—C9—H9B	108.2	C8—N3—C9	127.7 (4)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1ⁱⁱ	0.97	2.87	3.812 (5)	164
C5—H5···Cl2ⁱⁱⁱ	0.93	2.79	3.709 (5)	171

Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/4; (iii) y−1/2, −x+5/2, z−1/4.

Experimental details

Crystal data
Chemical formula	[CoCl₂(C₁₂H₁₄ClN₃)₂]
M_r	601.25
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	293
a, c (Å)	9.5706 (8), 29.911 (4)
V (Å³)	2739.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.32 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.763, 0.829
No. of measured, independent and observed [I > 2σ(I)] reflections	14573, 2703, 2219
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.131, 1.01
No. of reflections	2703
No. of parameters	169
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.80
Absolute structure	Flack (1983), 1274 Friedel pairs
Absolute structure parameter	0.07 (5)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1998) and ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Co1—N2	2.026 (4)	Co1—Cl2	2.2423 (13)

N2ⁱ—Co1—N2	103.8 (2)	Cl2—Co1—Cl2ⁱ	110.64 (7)
N2—Co1—Cl2	109.08 (12)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl1ⁱⁱ	0.97	2.87	3.812 (5)	164
C5—H5···Cl2ⁱⁱⁱ	0.93	2.79	3.709 (5)	171

Symmetry codes: (ii) −x+3/2, y−1/2, −z+1/4; (iii) y−1/2, −x+5/2, z−1/4.

Acknowledgements

This project was supported by the Nature Science Foundation of China (grant No. 20475026).

References

Balamurugan, V., Hundal, M. S. & Mukherjee, R. (2004). Chem. Eur. J. 10, 1683–1690. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Volume 64| Part 7| July 2008| Pages m942-m943

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­chloridobis[2-(2-chloro­ethyl)-1,2,3,4-tetra­hydro­pyrazino[1,2-a]benzimidazole-κN]cobalt(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichloridobis[2-(2-chloroethyl)-1,2,3,4-tetrahydropyrazino[1,2-a]benzimidazole-κN]cobalt(II)