catena-Poly[[chloridocobalt(II)]-μ-5-(8-quinolyloxymeth­yl)tetra­zolato-κ4N5,O,N1:N4]

Wang, G.-X.; Ye, H.-Y.

doi:10.1107/S1600536808020205

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1006

doi:10.1107/S1600536808020205

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catena-Poly[[chloridocobalt(II)]-μ-5-(8-quinolyloxymethyl)tetrazolato-κ⁴N⁵,O,N¹:N⁴]

Guo-Xi Wang ^a and Heng-Yun Ye ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: hyye@seu.edu.cn

(Received 18 June 2008; accepted 2 July 2008; online 9 July 2008)

In the title compound, [Co(C₁₁H₈N₅O)Cl]_n, the Co^II atom is pentacoordinated by one O atom and two N atoms from a 5-(8-quinolyloxymethyl)tetrazolate ligand, one N atom from another symmetry-related ligand, and a Cl atom. The coordination geometry can be described as slightly distorted trigonal–bipyramidal. Adjacent Co atoms are connected by the bridging tetrazole groups into a chain. The dihedral angle between the quinoline and tetrazole planes is 21.2 (1)°. The structure involves intra- and interchain C—H⋯N hydrogen bonds.

Related literature

For related literature, see: Luo & Ye (2008 ); Wang et al. (2005 ); Wang & Ye (2007 ); Xiong et al. (2002 ).

Experimental

Crystal data

[Co(C₁₁H₈N₅O)Cl]
M_r = 320.60
Monoclinic, P 2₁ /c
a = 7.0289 (11) Å
b = 8.4331 (11) Å
c = 20.220 (4) Å
β = 96.757 (10)°
V = 1190.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.66 mm⁻¹
T = 293 (2) K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku SCXmini CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.701, T_max = 0.798
12192 measured reflections
2846 independent reflections
2385 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.08
2846 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—N1ⁱ	2.049 (2)
Co1—N4	2.053 (2)
Co1—N5	2.066 (2)
Co1—Cl1	2.2670 (8)
Co1—O1	2.3979 (18)

N1ⁱ—Co1—N4	96.46 (9)
N1ⁱ—Co1—N5	106.43 (8)
N4—Co1—N5	134.43 (8)
N1ⁱ—Co1—Cl1	104.93 (7)
N4—Co1—Cl1	106.62 (7)
N5—Co1—Cl1	104.74 (6)
N1ⁱ—Co1—O1	86.22 (8)
N4—Co1—O1	70.65 (7)
N5—Co1—O1	72.16 (7)
Cl1—Co1—O1	168.82 (6)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯N3ⁱⁱ	0.97	2.54	3.292 (4)	135
C8—H8A⋯N2ⁱⁱⁱ	0.93	2.52	3.398 (4)	157
Symmetry codes: (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020205/hy2140sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020205/hy2140Isup2.hkl

checkCIF report

Comment top

In the past five years, we have focused on the chemistry of 5-substituted tetrazoles because of their multiple coordination modes to metal ions and the construction of novel metal–organic frameworks. (Wang et al., 2005; Xiong et al., 2002). As part of our on going studies of the chemistry of tetrazoles, we have determined the crystal structure of the title compound.

In the title compound, the Co^II atom is penta-coordinated by one O atom and two N atoms from an 8-[(tetrazol-5-yl)methoxy]quinoline ligand, by one N atom from another symmetry-related ligand, and by one terminal Cl atom (Fig. 1). The coordination geometry can be described as slightly distorted trigonal–bipyramidal (Table 1), with three N atoms (N4, N5 and N1ⁱ) [symmetry code: (i) -x + 1, y + 1/2, -z + 1/2] forming the equatorial palne and the O1 and Cl1 atoms occupying the axial positions. The deviation of the Co1 atom from the equatorial plane is 0.549 (1) Å. The bond angles of N4—Co1—N5, N5—Co1—N1ⁱ and N4—Co1—N1ⁱ are 134.43 (8), 106.43 (8) and 96.46 (9)°, respectively. Adjacent Co atoms are connected by the bridging tetrazole groups into a chain (Fig. 2). Geometric parameters of the ligand are in normal ranges (Wang & Ye, 2007). The dihedral angle between the quinoline and tetrazole planes is 21.2 (1)°. The structure involves intrachain and interchain C—H···N hydrogen bonds (Fig. 3; Table 2).

Related literature top

For related literature, see: Luo & Ye (2008); Wang et al. (2005); Wang & Ye (2007); Xiong et al. (2002).

Experimental top

8-(1H-Tetrazol-5-yl)methoxy)quinoline was synthesized by using a similar procedure described previously by us (Luo & Ye, 2008). A mixture of the ligand (0.045 g, 0.2 mmol), CoCl₂ (0.026 g, 0.2 mmol) and water (1 ml) was sealed in a glass tube and maintained at 383 K. Purple crystals of the title compound suitable for X-ray ananlysis were obtained after 3 d.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x + 1, y + 1/2, -z + 1/2.]
	Fig. 2. A polyhedral drawing of the chain in the title compound.
	Fig. 3. Crystal packing of the title compound viewed along the a-axis. Dashed lines denote hydrogen bonds. [Symmetry codes: (ii) -x + 1, y - 1/2, -z + 1/2; (iv) x + 1, -y + 1/2, z + 1/2.]

catena-Poly[[chloridocobalt(II)]-µ-5-(8-quinolyloxymethyl)tetrazolato- κ⁴N⁵,O,N¹:N⁴] top

Crystal data top

[Co(C₁₁H₈N₅O)Cl]	F(000) = 644
M_r = 320.60	D_x = 1.789 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2846 reflections
a = 7.0289 (11) Å	θ = 2.6–27.9°
b = 8.4331 (11) Å	µ = 1.66 mm⁻¹
c = 20.220 (4) Å	T = 293 K
β = 96.757 (10)°	Prism, purple
V = 1190.2 (3) Å³	0.20 × 0.18 × 0.14 mm
Z = 4

Data collection top

Rigaku SCXmini CCD area-detector diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	2385 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.9°, θ_min = 2.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.701, T_max = 0.798	l = −26→26
12192 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0449P)² + 0.5457P] where P = (F_o² + 2F_c²)/3
2846 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Co(C₁₁H₈N₅O)Cl]	V = 1190.2 (3) Å³
M_r = 320.60	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0289 (11) Å	µ = 1.66 mm⁻¹
b = 8.4331 (11) Å	T = 293 K
c = 20.220 (4) Å	0.20 × 0.18 × 0.14 mm
β = 96.757 (10)°

Data collection top

Rigaku SCXmini CCD area-detector diffractometer	2846 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2385 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.798	R_int = 0.047
12192 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	Δρ_max = 0.39 e Å⁻³
2846 reflections	Δρ_min = −0.37 e Å⁻³
172 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.19156 (5)	0.40223 (4)	0.221382 (16)	0.02932 (13)
C1	0.5028 (3)	0.1574 (3)	0.24542 (12)	0.0287 (5)
C2	0.4852 (4)	0.1332 (4)	0.17171 (13)	0.0380 (6)
H2A	0.6097	0.1391	0.1556	0.046*
H2B	0.4281	0.0310	0.1596	0.046*
C3	0.2568 (4)	0.2342 (3)	0.08430 (11)	0.0279 (5)
C4	0.3194 (4)	0.1528 (4)	0.03257 (13)	0.0376 (6)
H4A	0.4403	0.1065	0.0375	0.045*
C5	0.1997 (4)	0.1392 (4)	−0.02832 (13)	0.0404 (7)
H5A	0.2424	0.0841	−0.0636	0.049*
C6	0.0216 (4)	0.2065 (3)	−0.03590 (13)	0.0369 (6)
H6A	−0.0553	0.1978	−0.0764	0.044*
C7	−0.0466 (4)	0.2890 (3)	0.01735 (12)	0.0303 (5)
C8	−0.2301 (4)	0.3590 (4)	0.01327 (14)	0.0403 (6)
H8A	−0.3132	0.3524	−0.0260	0.048*
C9	−0.2846 (4)	0.4360 (4)	0.06704 (15)	0.0454 (7)
H9A	−0.4052	0.4825	0.0647	0.054*
C10	−0.1581 (4)	0.4453 (4)	0.12616 (14)	0.0375 (6)
H10A	−0.1980	0.4984	0.1624	0.045*
C11	0.0727 (3)	0.3037 (3)	0.07850 (11)	0.0253 (5)
N1	0.6256 (3)	0.0865 (3)	0.29043 (10)	0.0303 (5)
N2	0.5887 (3)	0.1467 (3)	0.34993 (10)	0.0362 (5)
N3	0.4486 (3)	0.2482 (3)	0.34007 (11)	0.0359 (5)
N4	0.3906 (3)	0.2574 (3)	0.27357 (10)	0.0309 (5)
N5	0.0151 (3)	0.3818 (2)	0.13259 (10)	0.0272 (4)
Cl1	−0.00233 (11)	0.49197 (11)	0.29524 (4)	0.0531 (2)
O1	0.3637 (3)	0.2596 (2)	0.14477 (8)	0.0324 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0282 (2)	0.0378 (2)	0.02076 (19)	0.00290 (14)	−0.00200 (13)	−0.00415 (14)
C1	0.0287 (12)	0.0331 (13)	0.0232 (12)	0.0014 (10)	−0.0014 (9)	0.0009 (10)
C2	0.0440 (16)	0.0439 (16)	0.0246 (13)	0.0178 (12)	−0.0024 (11)	0.0015 (12)
C3	0.0333 (13)	0.0308 (12)	0.0183 (11)	0.0017 (10)	−0.0019 (9)	0.0010 (10)
C4	0.0387 (15)	0.0451 (15)	0.0286 (13)	0.0113 (12)	0.0018 (11)	−0.0043 (12)
C5	0.0511 (17)	0.0481 (16)	0.0221 (13)	0.0060 (13)	0.0041 (11)	−0.0077 (12)
C6	0.0450 (15)	0.0441 (16)	0.0197 (12)	0.0004 (12)	−0.0036 (11)	−0.0027 (11)
C7	0.0346 (13)	0.0333 (13)	0.0217 (12)	−0.0004 (10)	−0.0026 (10)	0.0012 (10)
C8	0.0356 (15)	0.0532 (17)	0.0287 (14)	0.0039 (12)	−0.0099 (11)	−0.0020 (13)
C9	0.0330 (14)	0.063 (2)	0.0376 (16)	0.0142 (13)	−0.0065 (12)	−0.0070 (14)
C10	0.0343 (14)	0.0457 (16)	0.0312 (14)	0.0101 (12)	−0.0011 (11)	−0.0056 (12)
C11	0.0283 (12)	0.0278 (12)	0.0189 (11)	−0.0020 (9)	−0.0010 (9)	0.0001 (9)
N1	0.0345 (11)	0.0343 (11)	0.0204 (10)	−0.0012 (9)	−0.0031 (8)	0.0026 (8)
N2	0.0473 (14)	0.0382 (12)	0.0214 (11)	−0.0021 (10)	−0.0027 (9)	0.0010 (9)
N3	0.0448 (13)	0.0405 (13)	0.0216 (10)	−0.0018 (10)	0.0005 (9)	0.0005 (9)
N4	0.0357 (12)	0.0329 (11)	0.0235 (10)	−0.0008 (9)	0.0012 (9)	−0.0010 (9)
N5	0.0286 (10)	0.0318 (11)	0.0205 (10)	0.0008 (8)	−0.0008 (8)	−0.0019 (8)
Cl1	0.0478 (4)	0.0800 (6)	0.0326 (4)	0.0160 (4)	0.0090 (3)	−0.0097 (4)
O1	0.0347 (10)	0.0374 (10)	0.0227 (9)	0.0098 (7)	−0.0072 (7)	−0.0021 (8)

Geometric parameters (Å, º) top

Co1—N1ⁱ	2.049 (2)	C5—H5A	0.9300
Co1—N4	2.053 (2)	C6—C7	1.413 (4)
Co1—N5	2.066 (2)	C6—H6A	0.9300
Co1—Cl1	2.2670 (8)	C7—C8	1.412 (4)
Co1—O1	2.3979 (18)	C7—C11	1.415 (3)
C1—N1	1.321 (3)	C8—C9	1.360 (4)
C1—N4	1.327 (3)	C8—H8A	0.9300
C1—C2	1.495 (3)	C9—C10	1.406 (4)
C2—O1	1.433 (3)	C9—H9A	0.9300
C2—H2A	0.9700	C10—N5	1.322 (3)
C2—H2B	0.9700	C10—H10A	0.9300
C3—C4	1.366 (3)	C11—N5	1.378 (3)
C3—O1	1.375 (3)	N1—N2	1.359 (3)
C3—C11	1.413 (3)	N1—Co1ⁱⁱ	2.049 (2)
C4—C5	1.412 (4)	N2—N3	1.302 (3)
C4—H4A	0.9300	N3—N4	1.361 (3)
C5—C6	1.366 (4)

N1ⁱ—Co1—N4	96.46 (9)	C7—C6—H6A	119.7
N1ⁱ—Co1—N5	106.43 (8)	C8—C7—C6	123.4 (2)
N4—Co1—N5	134.43 (8)	C8—C7—C11	117.3 (2)
N1ⁱ—Co1—Cl1	104.93 (7)	C6—C7—C11	119.3 (2)
N4—Co1—Cl1	106.62 (7)	C9—C8—C7	119.6 (2)
N5—Co1—Cl1	104.74 (6)	C9—C8—H8A	120.2
N1ⁱ—Co1—O1	86.22 (8)	C7—C8—H8A	120.2
N4—Co1—O1	70.65 (7)	C8—C9—C10	119.8 (3)
N5—Co1—O1	72.16 (7)	C8—C9—H9A	120.1
Cl1—Co1—O1	168.82 (6)	C10—C9—H9A	120.1
N1—C1—N4	111.4 (2)	N5—C10—C9	123.0 (3)
N1—C1—C2	126.6 (2)	N5—C10—H10A	118.5
N4—C1—C2	122.1 (2)	C9—C10—H10A	118.5
O1—C2—C1	104.7 (2)	N5—C11—C3	119.0 (2)
O1—C2—H2A	110.8	N5—C11—C7	122.4 (2)
C1—C2—H2A	110.8	C3—C11—C7	118.6 (2)
O1—C2—H2B	110.8	C1—N1—N2	105.3 (2)
C1—C2—H2B	110.8	C1—N1—Co1ⁱⁱ	129.11 (17)
H2A—C2—H2B	108.9	N2—N1—Co1ⁱⁱ	125.07 (16)
C4—C3—O1	124.6 (2)	N3—N2—N1	109.3 (2)
C4—C3—C11	121.3 (2)	N2—N3—N4	108.8 (2)
O1—C3—C11	114.1 (2)	C1—N4—N3	105.3 (2)
C3—C4—C5	119.7 (3)	C1—N4—Co1	124.09 (17)
C3—C4—H4A	120.1	N3—N4—Co1	130.42 (17)
C5—C4—H4A	120.1	C10—N5—C11	117.9 (2)
C6—C5—C4	120.6 (2)	C10—N5—Co1	120.22 (17)
C6—C5—H5A	119.7	C11—N5—Co1	121.84 (16)
C4—C5—H5A	119.7	C3—O1—C2	117.5 (2)
C5—C6—C7	120.5 (2)	C3—O1—Co1	112.87 (14)
C5—C6—H6A	119.7	C2—O1—Co1	116.81 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N3ⁱⁱ	0.97	2.54	3.292 (4)	135
C8—H8A···N2ⁱⁱⁱ	0.93	2.52	3.398 (4)	157

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₁H₈N₅O)Cl]
M_r	320.60
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.0289 (11), 8.4331 (11), 20.220 (4)
β (°)	96.757 (10)
V (Å³)	1190.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.66
Crystal size (mm)	0.20 × 0.18 × 0.14

Data collection
Diffractometer	Rigaku SCXmini CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.701, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	12192, 2846, 2385
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.08
No. of reflections	2846
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.37

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—N1ⁱ	2.049 (2)	Co1—Cl1	2.2670 (8)
Co1—N4	2.053 (2)	Co1—O1	2.3979 (18)
Co1—N5	2.066 (2)

N1ⁱ—Co1—N4	96.46 (9)	N5—Co1—Cl1	104.74 (6)
N1ⁱ—Co1—N5	106.43 (8)	N1ⁱ—Co1—O1	86.22 (8)
N4—Co1—N5	134.43 (8)	N4—Co1—O1	70.65 (7)
N1ⁱ—Co1—Cl1	104.93 (7)	N5—Co1—O1	72.16 (7)
N4—Co1—Cl1	106.62 (7)	Cl1—Co1—O1	168.82 (6)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N3ⁱⁱ	0.97	2.54	3.292 (4)	135
C8—H8A···N2ⁱⁱⁱ	0.93	2.52	3.398 (4)	157

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

Acknowledgements

This work was supported by a Start-up Grant to HYY from Southeast University.

References

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