Dichloridobis[2-(2-chloro-ethyl)-1,2,3,4-tetra-hydro-pyrazino[1,2-a]benzimidazole-κN]cobalt(II).

In the title compound, [CoCl(2)(C(12)H(14)ClN(3))(2)], the central Co(II) ion lies on a twofold rotation axis and adopts a distorted tetra-hedral coordination geometry defined by two N atoms from two 2-(2-chloro-ethyl)-1,2,3,4-tetra-hydro-pyrazino[1,2-a]benzimidazole ligands and two chloride anions. The Cl atom located in the side chain of the ligand is involved in inter-molecular C-H⋯Cl hydrogen bonding, which links neutral complex units into a one-dimensional right-handed helical chain running along a crystallographic 4(1) axis. Such hydrogen-bonded helical chains are connected to each other to form a homochiral three-dimensional supra-molecular network. One C atom of the 2-chloro-ethyl 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 = 601.25

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.131

S = 1.01

2703 reflections

169 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.80 e Å−3

Absolute structure: Flack (1983 ▶), 1274 Friedel pairs

Flack parameter: 0.07 (5)

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CoCl2(C12H14ClN3)2]	Z = 4
Mr = 601.25	F000 = 1236
Tetragonal, P41212	Dx = 1.458 Mg m−3
Hall symbol: P 4abw 2nw	Mo Kα radiation λ = 0.71073 Å
a = 9.5706 (8) Å	Cell parameters from 835 reflections
b = 9.5706 (8) Å	θ = 2.5–16.9º
c = 29.911 (4) Å	µ = 1.04 mm−1
α = 90º	T = 293 (2) K
β = 90º	Prism, blue
γ = 90º	0.32 × 0.21 × 0.18 mm
V = 2739.7 (5) Å3

Bruker SMART APEX CCD area-detector diffractometer	2703 independent reflections
Radiation source: sealed tube	2219 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
T = 293(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −11→7
Tmin = 0.763, Tmax = 0.829	k = −11→11
14573 measured reflections	l = −36→35

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055	w = 1/[σ2(Fo2) + (0.0877P)2 + 1.82P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.131	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.54 e Å−3
2703 reflections	Δρmin = −0.80 e Å−3
169 parameters	Extinction correction: none
2 restraints	Absolute structure: Flack (1983), 1274 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (5)
Secondary atom site location: difference Fourier map

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) .

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) ; (iii) .