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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.106
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N6     --  N7      ..       5.93 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N7     --  N8      ..       5.48 su

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

All H atoms were positioned geometrically and refined using a riding model with d(C—H)_methine = 0.98Å, d(C—H)_aryl = 0.93Å, U_iso = 1.2U_eq(C).

Computing details

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

	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)]

Crystal data

[Mn(C11H8N5O)(N3)]	F(000) = 652
Mr = 323.19	Dx = 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) Å^3	0.20 × 0.16 × 0.12 mm
Z = 4

Data collection

Rigaku, SCXmini diffractometer	3074 independent reflections
Radiation source: Fine-focus sealed tube	2472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 13.6612 pixels mm^-1	θmax = 27.9°, θmin = 2.8°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.820, Tmax = 0.886	l = −11→11
13382 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0431P)^2 + 0.2319P] where P = (Fo^2 + 2Fc^2)/3
3074 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Mn1—N6	2.135 (2)	C6—C7	1.415 (4)
Mn1—N4	2.184 (2)	C6—H6A	0.9300
Mn1—N1^i	2.188 (2)	C7—C11	1.411 (4)
Mn1—N5	2.247 (2)	C7—C8	1.412 (4)
Mn1—N6^ii	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—Mn1^iii	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—Mn1^ii	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—N1^i	96.42 (8)	C11—C7—C8	116.5 (3)
N4—Mn1—N1^i	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)
N1^i—Mn1—N5	91.43 (8)	C9—C8—H8A	119.7
N6—Mn1—N6^ii	79.85 (9)	C7—C8—H8A	119.7
N4—Mn1—N6^ii	89.90 (9)	C8—C9—C10	119.1 (3)
N1^i—Mn1—N6^ii	175.15 (8)	C8—C9—H9A	120.4
N5—Mn1—N6^ii	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
N1^i—Mn1—O1	100.11 (8)	C9—C10—H10A	118.4
N5—Mn1—O1	68.97 (7)	N5—C11—C7	122.7 (3)
N6^ii—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—Mn1^iii	132.27 (18)
O1—C2—C1	104.99 (19)	N2—N1—Mn1^iii	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—Mn1^ii	126.11 (18)
C5—C4—H4A	120.6	Mn1—N6—Mn1^ii	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)

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.