Poly[(μ2-azido-κ2N1:N1)[μ2-5-(8-quinolyloxymeth­yl)tetra­zolato-κ4N1,O,N5:N4]manganese(II)]

Chen, F.; Ye, H.-Y.

doi:10.1107/S1600536808022617

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1060

doi:10.1107/S1600536808022617

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Poly[(μ₂-azido-κ²N¹:N¹)[μ₂-5-(8-quinolyloxymethyl)tetrazolato-κ⁴N¹,O,N⁵:N⁴]manganese(II)]

Fang Chen ^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 1 July 2008; accepted 18 July 2008; online 23 July 2008)

In the structure of the title compound, [Mn(C₁₁H₈N₅O)(N₃)]_n, the Mn atoms are hexacoordinated by five N atoms and one O atom. The coordination polyhedron of the Mn atom is a slightly distorted octahedron. The Mn atoms are connected by azide anions with a μ₂-1,1 mode and by 5-(8-quinolyloxymethyl)tetrazolate ligands in a μ₂-η¹(N),η³-(N,N,O) fashion to form a two-dimensional framework parallel to the (100) plane. Geometric parameters of the organic ligand are in the normal ranges and the dihedral angle between the quinoline ring system and the tetrazole unit is 7.41 (15)°. The structure involves intra- and intermolecular C—H⋯N hydrogen bonds.

Related literature

For the use of tetrazole derivatives in coordination chemistry, see: Wang et al. (2005 ); Xiong et al. (2002 ). For the crystal structure of a tetrazole derivative, see: Wang & Ye (2007 ); For the synthesis of 8-cyanatoquinoline, see: Luo & Ye (2008 ).

Experimental

Crystal data

[Mn(C₁₁H₈N₅O)(N₃)]
M_r = 323.19
Monoclinic, P 2₁ /c
a = 10.431 (2) Å
b = 14.431 (3) Å
c = 8.589 (2) Å
β = 90.676 (18)°
V = 1292.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 (2) K
0.20 × 0.16 × 0.12 mm

Data collection

Rigaku, SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.820, T_max = 0.886
13382 measured reflections
3074 independent reflections
2472 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.105
S = 1.11
3074 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯N8ⁱ	0.97	2.50	3.223 (4)	131
C5—H5A⋯N3ⁱⁱ	0.93	2.49	3.413 (4)	173
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

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/S1600536808022617/rk2100sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022617/rk2100Isup2.hkl

checkCIF report

Comment top

In the past five years, we have focused on the chemistry of 5–substituted tetrazole because of their multiple coordination modes as ligand to metal ions and the construction of novel metal–organic framework (Wang et al. 2005; Xiong et al. 2002). As part of our on going studies of the chemistry of tetrazole, we determined the crystal structure of the title compound, catena–[(µ₂–1,1–azido)–(µ₂– η¹(N), η³–(N,N,O)–((tetrazol–5–yl)methoxy) quinoline)–Manganese], I (Fig. 1).

As shown in Fig. 1, Mn1 is hexa–coordinated by five N and one O atoms, of which two N atoms and one O atom are from one organic ligand (tetrazol–5–yl)methoxy–quinoline, one N atom is from the tetrazole unit of another symmetry–related organic ligand (symmetry code: (iv) x, 3/2-y, 1/2+z) and two N atoms are from two azido anions which are symmetry–related (symmetry code: (iii) 1-x, 2-y, -z). The coordinated geometry of Mn1 is a distorted octahedron. The N4, N5, O1 and N6 atoms form the equatorial plane with mean deviation 0.1615Å of the plane (N4, N5, N6, O1 and Mn1). Geometry parameters of organic ligand are in normal ranges (Wang & Ye, 2007), dihedral angle of quinoline unit and the tetrazole unit is 7.41 (15)°. The Mn atoms are connected by azido anions and by (tetrazol–5–yl)methoxy–quinoline) ligands to form two–dimensional net framework parallel to the (1 0 0) plane (Fig.2). Beside the van der Waals forces, the crystal structure of I is also stabilized by intermolecular C—H···Nⁱⁱ hydrogen bonds. Symmetry code: (ii) x-1, y, z (Fig. 3).

Related literature top

For the use of tetrazole derivatives in coordination chemisty, see: Wang et al. (2005); Xiong et al. (2002). For crystal data of a tetrazole derivative, see: Wang & Ye (2007); For synthesis of 8–cyanatoquinoline, see: Luo & Ye (2008).

Experimental top

The precusor organic compound 8–cyanatoquinoline is was synthesized by using a similar procedure described by us before (Luo & Ye, 2008).A mixture of the organic ligand (34 mg, 0.2 mmol), NaN₃ (20 mg, 0.3 mmol), MnCl₂(25 mg, 0.2 mmol) and water (1 ml) sealed in a glass tube was maintained at 423 K. Yellow crystals suitable for X–ray analysis were obtained after 2 days.

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 fragment structure of I showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The hydrogen atoms are presented as small spheres of arbitrary radius. Symmetry codes: (iii) 1-x, 2-y, -z; (iv) x, 3/2-y, 1/2+z.
	Fig. 2. Two–dimensional net framework of the title compound view along a axis and all hydrogen atoms are omitted for clarity.
	Fig. 3. Crystal packing of the title compound viewed along the c axis. Hydrogen atoms not included in intermolecular hydrogen bonds are omitted for clarity. Dashed lines show the intermolecular hydrogen bonds.

Poly[(µ₂-azido-κ²N¹:N¹)[µ₂-5-(8-quinolyloxymethyl)tetrazolato- κ⁴N¹,O,N⁵:N⁴]manganese(II)] top

Crystal data top

[Mn(C₁₁H₈N₅O)(N₃)]	F(000) = 652
M_r = 323.19	D_x = 1.661 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3074 reflections
a = 10.431 (2) Å	θ = 2.8–27.9°
b = 14.431 (3) Å	µ = 1.03 mm⁻¹
c = 8.589 (2) Å	T = 293 K
β = 90.676 (18)°	Block, yellow
V = 1292.8 (5) Å³	0.20 × 0.16 × 0.12 mm
Z = 4

Data collection top

Rigaku, SCXmini diffractometer	3074 independent reflections
Radiation source: Fine-focus sealed tube	2472 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.9°, θ_min = 2.8°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
T_min = 0.820, T_max = 0.886	l = −11→11
13382 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0431P)² + 0.2319P] where P = (F_o² + 2F_c²)/3
3074 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Mn(C₁₁H₈N₅O)(N₃)]	V = 1292.8 (5) Å³
M_r = 323.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.431 (2) Å	µ = 1.03 mm⁻¹
b = 14.431 (3) Å	T = 293 K
c = 8.589 (2) Å	0.20 × 0.16 × 0.12 mm
β = 90.676 (18)°

Data collection top

Rigaku, SCXmini diffractometer	3074 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2472 reflections with I > 2σ(I)
T_min = 0.820, T_max = 0.886	R_int = 0.054
13382 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.11	Δρ_max = 0.32 e Å⁻³
3074 reflections	Δρ_min = −0.41 e Å⁻³
190 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Mn1	0.44828 (3)	0.90619 (3)	0.09904 (4)	0.03138 (13)
C1	0.4312 (2)	0.72913 (17)	−0.1025 (3)	0.0347 (6)
C2	0.2897 (2)	0.74195 (18)	−0.0956 (3)	0.0361 (6)
H2A	0.2548	0.7575	−0.1974	0.043*
H2B	0.2484	0.6860	−0.0588	0.043*
C3	0.1497 (2)	0.84401 (18)	0.0504 (3)	0.0369 (6)
C4	0.0389 (3)	0.8016 (2)	0.0034 (4)	0.0489 (7)
H4A	0.0410	0.7513	−0.0642	0.059*
C5	−0.0791 (3)	0.8355 (2)	0.0595 (5)	0.0636 (9)
H5A	−0.1549	0.8068	0.0280	0.076*
C6	−0.0843 (3)	0.9086 (2)	0.1577 (5)	0.0611 (9)
H6A	−0.1631	0.9291	0.1939	0.073*
C7	0.0296 (3)	0.9541 (2)	0.2056 (4)	0.0476 (7)
C8	0.0335 (3)	1.0319 (2)	0.3054 (4)	0.0598 (9)
H8A	−0.0425	1.0565	0.3429	0.072*
C9	0.1473 (3)	1.0708 (2)	0.3471 (4)	0.0622 (9)
H9A	0.1498	1.1213	0.4144	0.075*
C10	0.2607 (3)	1.0341 (2)	0.2875 (3)	0.0506 (7)
H10A	0.3380	1.0617	0.3161	0.061*
C11	0.1485 (2)	0.92186 (18)	0.1507 (3)	0.0350 (6)
N1	0.4916 (2)	0.66357 (15)	−0.1804 (3)	0.0402 (5)
N2	0.6184 (2)	0.67775 (19)	−0.1497 (3)	0.0551 (7)
N3	0.6309 (2)	0.74859 (19)	−0.0569 (3)	0.0569 (7)
N4	0.5125 (2)	0.78285 (16)	−0.0251 (3)	0.0431 (6)
N5	0.2634 (2)	0.96208 (15)	0.1926 (2)	0.0372 (5)
N6	0.5787 (2)	1.01876 (16)	0.1316 (3)	0.0417 (5)
N7	0.6346 (2)	1.04671 (15)	0.2407 (3)	0.0415 (5)
N8	0.6923 (3)	1.0756 (2)	0.3458 (3)	0.0701 (9)
O1	0.27145 (16)	0.81654 (12)	0.0115 (2)	0.0398 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0286 (2)	0.0303 (2)	0.0353 (2)	−0.00417 (15)	0.00011 (15)	0.00057 (15)
C1	0.0352 (14)	0.0325 (13)	0.0364 (13)	−0.0005 (10)	−0.0019 (11)	−0.0022 (10)
C2	0.0345 (14)	0.0334 (13)	0.0403 (14)	−0.0042 (11)	−0.0015 (11)	−0.0079 (11)
C3	0.0272 (12)	0.0390 (14)	0.0445 (15)	0.0012 (10)	0.0001 (11)	0.0068 (11)
C4	0.0340 (15)	0.0462 (17)	0.067 (2)	−0.0052 (12)	−0.0026 (13)	−0.0041 (14)
C5	0.0276 (15)	0.061 (2)	0.102 (3)	−0.0051 (14)	−0.0040 (16)	0.004 (2)
C6	0.0306 (15)	0.067 (2)	0.086 (3)	0.0049 (14)	0.0069 (16)	0.0028 (18)
C7	0.0363 (15)	0.0509 (17)	0.0558 (18)	0.0087 (13)	0.0078 (13)	0.0063 (14)
C8	0.0510 (19)	0.063 (2)	0.066 (2)	0.0169 (16)	0.0150 (16)	−0.0072 (17)
C9	0.057 (2)	0.063 (2)	0.066 (2)	0.0136 (17)	0.0090 (17)	−0.0211 (17)
C10	0.0492 (18)	0.0498 (18)	0.0529 (18)	−0.0006 (14)	0.0013 (14)	−0.0121 (14)
C11	0.0291 (13)	0.0397 (14)	0.0362 (14)	0.0020 (10)	0.0031 (10)	0.0072 (10)
N1	0.0336 (12)	0.0408 (13)	0.0461 (13)	0.0030 (9)	−0.0019 (10)	−0.0086 (10)
N2	0.0372 (13)	0.0645 (17)	0.0633 (17)	0.0066 (12)	−0.0057 (12)	−0.0228 (13)
N3	0.0349 (13)	0.0648 (17)	0.0708 (18)	0.0001 (12)	−0.0065 (12)	−0.0225 (14)
N4	0.0322 (12)	0.0428 (13)	0.0541 (14)	0.0026 (10)	−0.0034 (10)	−0.0125 (11)
N5	0.0346 (11)	0.0379 (12)	0.0392 (12)	0.0015 (9)	0.0021 (9)	−0.0013 (9)
N6	0.0456 (13)	0.0389 (12)	0.0405 (13)	−0.0140 (10)	−0.0067 (10)	0.0060 (10)
N7	0.0433 (13)	0.0348 (12)	0.0464 (14)	−0.0020 (10)	0.0019 (11)	0.0010 (10)
N8	0.083 (2)	0.073 (2)	0.0529 (17)	−0.0068 (16)	−0.0253 (16)	−0.0143 (14)
O1	0.0290 (9)	0.0403 (10)	0.0501 (11)	−0.0026 (8)	0.0035 (8)	−0.0124 (8)

Geometric parameters (Å, º) top

Mn1—N6	2.135 (2)	C6—C7	1.415 (4)
Mn1—N4	2.184 (2)	C6—H6A	0.9300
Mn1—N1ⁱ	2.188 (2)	C7—C11	1.411 (4)
Mn1—N5	2.247 (2)	C7—C8	1.412 (4)
Mn1—N6ⁱⁱ	2.272 (2)	C8—C9	1.358 (5)
Mn1—O1	2.3682 (18)	C8—H8A	0.9300
C1—N4	1.322 (3)	C9—C10	1.399 (4)
C1—N1	1.322 (3)	C9—H9A	0.9300
C1—C2	1.490 (4)	C10—N5	1.322 (3)
C2—O1	1.430 (3)	C10—H10A	0.9300
C2—H2A	0.9700	C11—N5	1.376 (3)
C2—H2B	0.9700	N1—N2	1.361 (3)
C3—C4	1.364 (4)	N1—Mn1ⁱⁱⁱ	2.188 (2)
C3—O1	1.376 (3)	N2—N3	1.302 (3)
C3—C11	1.416 (4)	N3—N4	1.361 (3)
C4—C5	1.414 (4)	N6—N7	1.169 (3)
C4—H4A	0.9300	N6—Mn1ⁱⁱ	2.272 (2)
C5—C6	1.353 (5)	N7—N8	1.157 (3)
C5—H5A	0.9300

N6—Mn1—N4	119.03 (9)	C7—C6—H6A	119.9
N6—Mn1—N1ⁱ	96.42 (8)	C11—C7—C8	116.5 (3)
N4—Mn1—N1ⁱ	89.22 (9)	C11—C7—C6	119.2 (3)
N6—Mn1—N5	103.19 (9)	C8—C7—C6	124.3 (3)
N4—Mn1—N5	137.42 (8)	C9—C8—C7	120.5 (3)
N1ⁱ—Mn1—N5	91.43 (8)	C9—C8—H8A	119.7
N6—Mn1—N6ⁱⁱ	79.85 (9)	C7—C8—H8A	119.7
N4—Mn1—N6ⁱⁱ	89.90 (9)	C8—C9—C10	119.1 (3)
N1ⁱ—Mn1—N6ⁱⁱ	175.15 (8)	C8—C9—H9A	120.4
N5—Mn1—N6ⁱⁱ	92.44 (9)	C10—C9—H9A	120.4
N6—Mn1—O1	161.79 (8)	N5—C10—C9	123.2 (3)
N4—Mn1—O1	69.03 (7)	N5—C10—H10A	118.4
N1ⁱ—Mn1—O1	100.11 (8)	C9—C10—H10A	118.4
N5—Mn1—O1	68.97 (7)	N5—C11—C7	122.7 (3)
N6ⁱⁱ—Mn1—O1	84.01 (7)	N5—C11—C3	118.7 (2)
N4—C1—N1	111.6 (2)	C7—C11—C3	118.6 (3)
N4—C1—C2	122.5 (2)	C1—N1—N2	105.2 (2)
N1—C1—C2	125.9 (2)	C1—N1—Mn1ⁱⁱⁱ	132.27 (18)
O1—C2—C1	104.99 (19)	N2—N1—Mn1ⁱⁱⁱ	115.27 (17)
O1—C2—H2A	110.7	N3—N2—N1	109.1 (2)
C1—C2—H2A	110.7	N2—N3—N4	108.8 (2)
O1—C2—H2B	110.7	C1—N4—N3	105.3 (2)
C1—C2—H2B	110.7	C1—N4—Mn1	121.64 (17)
H2A—C2—H2B	108.8	N3—N4—Mn1	132.69 (18)
C4—C3—O1	125.4 (3)	C10—N5—C11	117.9 (2)
C4—C3—C11	121.5 (2)	C10—N5—Mn1	121.83 (19)
O1—C3—C11	113.0 (2)	C11—N5—Mn1	120.26 (17)
C3—C4—C5	118.8 (3)	N7—N6—Mn1	132.73 (19)
C3—C4—H4A	120.6	N7—N6—Mn1ⁱⁱ	126.11 (18)
C5—C4—H4A	120.6	Mn1—N6—Mn1ⁱⁱ	100.15 (9)
C6—C5—C4	121.6 (3)	N8—N7—N6	178.1 (3)
C6—C5—H5A	119.2	C3—O1—C2	120.2 (2)
C4—C5—H5A	119.2	C3—O1—Mn1	118.92 (15)
C5—C6—C7	120.2 (3)	C2—O1—Mn1	120.41 (14)
C5—C6—H6A	119.9

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N8^iv	0.97	2.50	3.223 (4)	131
C5—H5A···N3^v	0.93	2.49	3.413 (4)	173

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₁H₈N₅O)(N₃)]
M_r	323.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.431 (2), 14.431 (3), 8.589 (2)
β (°)	90.676 (18)
V (Å³)	1292.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Rigaku, SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.820, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	13382, 3074, 2472
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.106, 1.11
No. of reflections	3074
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.41

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N8ⁱ	0.97	2.50	3.223 (4)	131.4
C5—H5A···N3ⁱⁱ	0.93	2.49	3.413 (4)	173.3

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

Acknowledgements

This work was supported by a Start-up Grant awarded to Dr Heng-Yun Ye by Southeast University.

References

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