[(2-Pyrid-yl)methanol-κN,O]bis-(thio-cyanato-κN)manganese(II).

In the title complex, [Mn(NCS)(2)(C(6)H(7)NO)(2)], the Mn(II) atom shows site symmetry 2. The distorted octa-hedral environment of Mn(II) is defined by two N atoms [Mn-N = 2.217 (4) and 2.132 (5) Å] and one O atom [Mn-O 2.305 (4) Å]. There are inter-molecular O-H⋯S hydrogen bonds and inter-molecular π-π stacking inter-actions between adjacent (2-pyrid-yl)methano-late ligands [centroid-centroid distance = 3.5569 (7) Å], leading to a chain structure running along [100].

Related literature

For background to metallacrowns, see: Mezei et al. (2007 ▶); Lah & Pecoraro (1989 ▶). For manganese clusters, see: Christou et al. (2000 ▶). For 2-(hy­droxy­meth­yl)pyridine, see: Shieh et al. (1997 ▶). For bond lengths and angles in related structures, see: Ito & Onaka (2004 ▶).

Experimental

Crystal data

[Mn(NCS)2(C6H7NO)2]

M = 389.35

Orthorhombic,

a = 11.4759 (12) Å

b = 8.398 (1) Å

c = 17.9451 (18) Å

V = 1729.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.02 mm−1

T = 298 K

0.48 × 0.45 × 0.40 mm

Data collection

Rigaku SCXmini CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.641, T max = 0.687

7935 measured reflections

1521 independent reflections

1214 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.135

S = 1.35

1521 reflections

105 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.56 e Å−3

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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810034483/bg2365sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034483/bg2365Isup2.hkl

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

[Mn(NCS)2(C6H7NO)2]	F(000) = 796
Mr = 389.35	Dx = 1.495 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3027 reflections
a = 11.4759 (12) Å	θ = 2.3–25.0°
b = 8.398 (1) Å	µ = 1.02 mm−1
c = 17.9451 (18) Å	T = 298 K
V = 1729.5 (3) Å3	Prism, dark brown
Z = 4	0.48 × 0.45 × 0.40 mm

Rigaku model name? CCD area-detector diffractometer	1521 independent reflections
Radiation source: fine-focus sealed tube	1214 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 8.192 pixels mm-1	θmax = 25.0°, θmin = 2.3°
φ and ω scans	h = −8→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −8→9
Tmin = 0.641, Tmax = 0.687	l = −18→21
7935 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.35	w = 1/[σ2(Fo2) + (0.0123P)2 + 5.1205P] where P = (Fo2 + 2Fc2)/3
1521 reflections	(Δ/σ)max < 0.001
105 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

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
Mn1	0.5000	0.20604 (14)	0.2500	0.0459 (3)
S1	0.30922 (15)	−0.1799 (2)	0.08535 (9)	0.0699 (5)
N1	0.3448 (4)	0.2711 (5)	0.3170 (2)	0.0517 (12)
N2	0.4118 (5)	0.0404 (6)	0.1798 (3)	0.0635 (14)
O1	0.5552 (4)	0.3948 (5)	0.3363 (2)	0.0623 (11)
H1	0.6229	0.3775	0.3485	0.093*
C1	0.4838 (5)	0.3959 (8)	0.4006 (3)	0.0641 (17)
H1A	0.4863	0.5002	0.4238	0.077*
H1B	0.5124	0.3185	0.4363	0.077*
C2	0.3599 (5)	0.3560 (7)	0.3791 (3)	0.0528 (14)
C3	0.2673 (7)	0.4019 (8)	0.4232 (3)	0.0710 (19)
H3	0.2802	0.4609	0.4663	0.085*
C4	0.1568 (6)	0.3600 (9)	0.4032 (4)	0.077 (2)
H4	0.0935	0.3889	0.4326	0.092*
C5	0.1405 (6)	0.2744 (9)	0.3388 (4)	0.0731 (19)
H5	0.0658	0.2465	0.3234	0.088*
C6	0.2357 (5)	0.2308 (7)	0.2976 (3)	0.0600 (15)
H6	0.2243	0.1710	0.2546	0.072*
C7	0.3687 (5)	−0.0499 (7)	0.1405 (3)	0.0469 (13)

	U11	U22	U33	U12	U13	U23
Mn1	0.0442 (6)	0.0468 (6)	0.0466 (6)	0.000	0.0000 (5)	0.000
S1	0.0688 (10)	0.0746 (11)	0.0664 (10)	−0.0037 (9)	−0.0120 (8)	−0.0178 (9)
N1	0.053 (3)	0.055 (3)	0.047 (3)	0.005 (2)	0.003 (2)	0.006 (2)
N2	0.061 (3)	0.057 (3)	0.073 (3)	0.002 (3)	−0.010 (3)	−0.012 (3)
O1	0.056 (2)	0.074 (3)	0.057 (2)	−0.006 (2)	−0.003 (2)	−0.009 (2)
C1	0.068 (4)	0.078 (4)	0.046 (3)	0.014 (4)	−0.005 (3)	−0.007 (3)
C2	0.064 (4)	0.055 (3)	0.040 (3)	0.016 (3)	0.001 (3)	0.007 (3)
C3	0.091 (5)	0.076 (4)	0.047 (3)	0.023 (4)	0.007 (3)	0.007 (3)
C4	0.070 (5)	0.094 (5)	0.067 (4)	0.029 (4)	0.024 (4)	0.022 (4)
C5	0.052 (4)	0.090 (5)	0.077 (5)	0.014 (4)	0.007 (3)	0.024 (4)
C6	0.055 (4)	0.066 (4)	0.060 (4)	0.002 (3)	−0.001 (3)	0.011 (3)
C7	0.039 (3)	0.050 (3)	0.052 (3)	0.009 (3)	0.001 (3)	0.004 (3)

Mn1—N2	2.132 (5)	C1—C2	1.511 (8)
Mn1—N2i	2.132 (5)	C1—H1A	0.9700
Mn1—N1i	2.217 (4)	C1—H1B	0.9700
Mn1—N1	2.217 (4)	C2—C3	1.379 (8)
Mn1—O1	2.305 (4)	C3—C4	1.365 (10)
Mn1—O1i	2.305 (4)	C3—H3	0.9300
S1—C7	1.624 (6)	C4—C5	1.373 (10)
N1—C2	1.335 (7)	C4—H4	0.9300
N1—C6	1.343 (7)	C5—C6	1.368 (8)
N2—C7	1.148 (7)	C5—H5	0.9300
O1—C1	1.415 (6)	C6—H6	0.9300
O1—H1	0.8200
N2—Mn1—N2i	98.5 (3)	O1—C1—C2	109.6 (4)
N2—Mn1—N1i	102.81 (18)	O1—C1—H1A	109.7
N2i—Mn1—N1i	95.73 (19)	C2—C1—H1A	109.7
N2—Mn1—N1	95.73 (19)	O1—C1—H1B	109.7
N2i—Mn1—N1	102.81 (18)	C2—C1—H1B	109.7
N1i—Mn1—N1	151.5 (2)	H1A—C1—H1B	108.2
N2—Mn1—O1	167.46 (18)	N1—C2—C3	121.9 (6)
N2i—Mn1—O1	85.49 (17)	N1—C2—C1	117.0 (5)
N1i—Mn1—O1	88.50 (15)	C3—C2—C1	121.1 (6)
N1—Mn1—O1	71.76 (16)	C4—C3—C2	119.5 (6)
N2—Mn1—O1i	85.49 (17)	C4—C3—H3	120.3
N2i—Mn1—O1i	167.46 (18)	C2—C3—H3	120.3
N1i—Mn1—O1i	71.76 (16)	C3—C4—C5	118.9 (6)
N1—Mn1—O1i	88.50 (15)	C3—C4—H4	120.5
O1—Mn1—O1i	93.1 (2)	C5—C4—H4	120.5
C2—N1—C6	118.1 (5)	C6—C5—C4	119.0 (7)
C2—N1—Mn1	118.7 (4)	C6—C5—H5	120.5
C6—N1—Mn1	123.2 (4)	C4—C5—H5	120.5
C7—N2—Mn1	177.1 (5)	N1—C6—C5	122.6 (6)
C1—O1—Mn1	113.1 (3)	N1—C6—H6	118.7
C1—O1—H1	109.5	C5—C6—H6	118.7
Mn1—O1—H1	108.5	N2—C7—S1	179.0 (5)
N2—Mn1—N1—C2	168.6 (4)	Mn1—O1—C1—C2	−34.4 (6)
N2i—Mn1—N1—C2	68.5 (4)	C6—N1—C2—C3	0.2 (8)
N1i—Mn1—N1—C2	−60.7 (4)	Mn1—N1—C2—C3	179.4 (4)
O1—Mn1—N1—C2	−12.3 (4)	C6—N1—C2—C1	178.4 (5)
O1i—Mn1—N1—C2	−106.0 (4)	Mn1—N1—C2—C1	−2.3 (7)
N2—Mn1—N1—C6	−12.1 (5)	O1—C1—C2—N1	24.8 (7)
N2i—Mn1—N1—C6	−112.3 (4)	O1—C1—C2—C3	−156.9 (5)
N1i—Mn1—N1—C6	118.5 (4)	N1—C2—C3—C4	0.0 (9)
O1—Mn1—N1—C6	166.9 (5)	C1—C2—C3—C4	−178.2 (6)
O1i—Mn1—N1—C6	73.2 (4)	C2—C3—C4—C5	−0.8 (10)
N2—Mn1—O1—C1	30.2 (10)	C3—C4—C5—C6	1.4 (10)
N2i—Mn1—O1—C1	−79.2 (4)	C2—N1—C6—C5	0.5 (9)
N1i—Mn1—O1—C1	−175.1 (4)	Mn1—N1—C6—C5	−178.7 (5)
N1—Mn1—O1—C1	25.9 (4)	C4—C5—C6—N1	−1.3 (10)
O1i—Mn1—O1—C1	113.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1ii	0.82	2.49	3.297 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1i	0.82	2.49	3.297 (4)	167

Symmetry code: (i) .