Bis{N(2),N(6)-bis-[(pyridin-3-yl)meth-yl]pyridine-2,6-dicarboxamide-κN}bis-(methanol-κO)bis-(thio-cyanato-κN)cobalt(II).

In the title compound, [Co(NCS)(2)(C(19)H(17)N(5)O(2))(2)(CH(3)OH)(2)], the Co(II) atom lies on an inversion center and is coordinated by two isothio-cyanate N atoms, two O atoms of methanol mol-ecules and two pyridine N atoms in a slightly distorted octa-hedral environment. Inter-molecular O-H⋯O and N-H⋯N hydrogen bonds join the complex mol-ecules into layers parallel to the bc plane.

Related literature

For the coordination chemistry of pyridyl­carboxamides, see: Thompson (2002 ▶); Wu et al. (2008 ▶). For the architectures of complexes with pyridyl­carboxamide ligands and various metal ions, see: Uemura et al. (2002 ▶); Burchell et al. (2006 ▶).

Experimental

Crystal data

[Co(NCS)2(C19H17N5O2)2(CH4O)2]

M = 933.93

Monoclinic,

a = 9.6728 (19) Å

b = 17.631 (4) Å

c = 13.041 (3) Å

β = 100.13 (3)°

V = 2189.4 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.55 mm−1

T = 293 K

0.22 × 0.21 × 0.18 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.892, T max = 0.914

21676 measured reflections

3803 independent reflections

3435 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.101

S = 1.15

3803 reflections

291 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812020326/yk2057sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020326/yk2057Isup2.hkl

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

[Co(NCS)2(C19H17N5O2)2(CH4O)2]	F(000) = 970
Mr = 933.93	Dx = 1.417 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4895 reflections
a = 9.6728 (19) Å	θ = 2.1–30.8°
b = 17.631 (4) Å	µ = 0.55 mm−1
c = 13.041 (3) Å	T = 293 K
β = 100.13 (3)°	Block, pink
V = 2189.4 (8) Å3	0.22 × 0.21 × 0.18 mm
Z = 2

Siemens SMART CCD diffractometer	3803 independent reflections
Radiation source: fine-focus sealed tube	3435 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
ω scan	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.892, Tmax = 0.914	k = −20→20
21676 measured reflections	l = −15→15

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) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0359P)2 + 0.829P] where P = (Fo2 + 2Fc2)/3
3803 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
Co1	0.0000	0.0000	0.5000	0.03328 (16)
S1	−0.19041 (9)	0.20444 (5)	0.66597 (7)	0.0607 (3)
O1	0.3791 (3)	−0.10454 (13)	0.85021 (19)	0.0727 (7)
O2	0.0978 (2)	0.10649 (12)	1.22010 (16)	0.0622 (6)
O3	−0.0365 (2)	0.08401 (12)	0.38047 (17)	0.0472 (5)
N1	0.2436 (2)	0.02348 (12)	1.01554 (16)	0.0373 (5)
N2	0.3961 (2)	0.02276 (14)	0.86373 (18)	0.0463 (6)
H2A	0.3683	0.0635	0.8935	0.056*
N3	0.2057 (2)	0.16022 (13)	1.09943 (17)	0.0443 (6)
H3A	0.2468	0.1532	1.0451	0.053*
N4	0.2142 (2)	0.03865 (13)	0.54496 (17)	0.0397 (5)
N5	0.3318 (3)	0.30281 (16)	1.4128 (2)	0.0604 (7)
N6	−0.0655 (3)	0.07304 (14)	0.60659 (18)	0.0458 (6)
C1	0.3501 (3)	−0.04486 (18)	0.8894 (2)	0.0471 (7)
C2	0.2582 (3)	−0.04329 (16)	0.9707 (2)	0.0409 (7)
C3	0.1951 (3)	−0.10950 (17)	0.9980 (2)	0.0533 (8)
H3	0.2049	−0.1558	0.9628	0.064*
C4	0.1183 (3)	−0.10634 (19)	1.0772 (3)	0.0583 (9)
H4	0.0753	−0.1508	1.0983	0.070*
C5	0.1043 (3)	−0.03805 (18)	1.1255 (2)	0.0497 (8)
H5	0.0521	−0.0346	1.1806	0.060*
C6	0.1676 (3)	0.02553 (15)	1.0922 (2)	0.0386 (7)
C7	0.1543 (3)	0.10093 (17)	1.1426 (2)	0.0419 (7)
C8	0.4895 (3)	0.0323 (2)	0.7894 (2)	0.0536 (8)
H8A	0.5457	−0.0145	0.7886	0.064*
H8B	0.5554	0.0742	0.8134	0.064*
C9	0.4171 (3)	0.04924 (16)	0.6792 (2)	0.0405 (7)
C10	0.2796 (3)	0.02987 (16)	0.6441 (2)	0.0420 (7)
H10	0.2275	0.0090	0.6926	0.050*
C11	0.2886 (3)	0.06854 (17)	0.4779 (2)	0.0509 (8)
H11	0.2453	0.0745	0.4071	0.061*
C12	0.4252 (4)	0.0909 (2)	0.5080 (3)	0.0633 (9)
H12	0.4747	0.1132	0.4588	0.076*
C13	0.4904 (3)	0.08126 (19)	0.6091 (3)	0.0566 (9)
H13	0.5853	0.0965	0.6306	0.068*
C14	0.1958 (4)	0.23665 (17)	1.1399 (2)	0.0537 (8)
H14A	0.0988	0.2452	1.1519	0.064*
H14B	0.2145	0.2736	1.0867	0.064*
C15	0.2965 (3)	0.25142 (15)	1.2399 (2)	0.0419 (7)
C16	0.4374 (4)	0.23449 (18)	1.2524 (3)	0.0594 (9)
H16	0.4747	0.2111	1.1975	0.071*
C17	0.5232 (4)	0.2516 (2)	1.3443 (3)	0.0665 (10)
H17	0.6207	0.2403	1.3541	0.080*
C18	0.4669 (4)	0.28538 (19)	1.4224 (3)	0.0620 (9)
H18	0.5273	0.2968	1.4861	0.074*
C19	0.2503 (3)	0.28563 (17)	1.3221 (2)	0.0522 (8)
H19	0.1533	0.2980	1.3139	0.063*
C20	−0.1081 (5)	0.1531 (2)	0.3779 (3)	0.0936 (15)
H20A	−0.1899	0.1473	0.4122	0.140*
H20B	−0.1394	0.1686	0.3053	0.140*
H20C	−0.0453	0.1919	0.4143	0.140*
C21	−0.1174 (3)	0.12750 (16)	0.6318 (2)	0.0387 (6)
H1	0.005 (3)	0.0815 (17)	0.336 (2)	0.045 (10)*

	U11	U22	U33	U12	U13	U23
Co1	0.0331 (3)	0.0375 (3)	0.0294 (3)	0.0044 (2)	0.0059 (2)	0.0039 (2)
S1	0.0654 (6)	0.0427 (5)	0.0790 (6)	0.0000 (4)	0.0261 (5)	−0.0131 (4)
O1	0.0898 (19)	0.0547 (14)	0.0772 (17)	0.0137 (13)	0.0244 (14)	−0.0174 (13)
O2	0.0804 (17)	0.0688 (15)	0.0449 (13)	0.0054 (12)	0.0318 (12)	0.0063 (11)
O3	0.0517 (13)	0.0519 (13)	0.0415 (12)	0.0129 (10)	0.0179 (11)	0.0156 (10)
N1	0.0372 (13)	0.0400 (13)	0.0322 (12)	0.0034 (10)	−0.0006 (10)	−0.0006 (10)
N2	0.0466 (15)	0.0544 (16)	0.0378 (13)	0.0025 (12)	0.0067 (11)	−0.0090 (11)
N3	0.0574 (16)	0.0449 (14)	0.0341 (13)	−0.0024 (12)	0.0176 (12)	−0.0015 (11)
N4	0.0358 (13)	0.0479 (14)	0.0352 (13)	−0.0013 (11)	0.0063 (10)	0.0022 (11)
N5	0.0644 (19)	0.0654 (18)	0.0547 (17)	−0.0038 (15)	0.0195 (15)	−0.0203 (14)
N6	0.0497 (15)	0.0484 (15)	0.0415 (14)	0.0059 (12)	0.0143 (12)	−0.0012 (12)
C1	0.0476 (18)	0.0490 (19)	0.0406 (17)	0.0103 (15)	−0.0035 (14)	−0.0062 (15)
C2	0.0404 (16)	0.0441 (17)	0.0344 (15)	0.0043 (13)	−0.0043 (12)	0.0014 (13)
C3	0.056 (2)	0.0406 (18)	0.057 (2)	0.0008 (15)	−0.0057 (16)	−0.0021 (15)
C4	0.060 (2)	0.051 (2)	0.062 (2)	−0.0100 (16)	0.0035 (17)	0.0104 (17)
C5	0.0493 (18)	0.057 (2)	0.0419 (17)	−0.0049 (15)	0.0047 (14)	0.0100 (15)
C6	0.0362 (15)	0.0459 (17)	0.0321 (15)	0.0021 (13)	0.0016 (12)	0.0063 (12)
C7	0.0413 (16)	0.0553 (19)	0.0288 (15)	0.0063 (14)	0.0057 (13)	0.0040 (13)
C8	0.0359 (17)	0.077 (2)	0.0457 (18)	−0.0008 (16)	0.0012 (14)	−0.0087 (16)
C9	0.0336 (15)	0.0451 (16)	0.0421 (16)	0.0006 (13)	0.0049 (13)	−0.0066 (13)
C10	0.0400 (16)	0.0530 (18)	0.0337 (15)	−0.0002 (14)	0.0082 (13)	0.0005 (13)
C11	0.0484 (18)	0.062 (2)	0.0426 (18)	−0.0015 (16)	0.0094 (15)	0.0125 (15)
C12	0.057 (2)	0.080 (2)	0.058 (2)	−0.0173 (18)	0.0216 (17)	0.0120 (18)
C13	0.0409 (18)	0.068 (2)	0.061 (2)	−0.0175 (16)	0.0086 (16)	−0.0059 (17)
C14	0.070 (2)	0.0449 (18)	0.0483 (18)	0.0091 (16)	0.0159 (16)	−0.0003 (15)
C15	0.0495 (18)	0.0343 (15)	0.0444 (17)	0.0026 (13)	0.0153 (14)	−0.0027 (13)
C16	0.063 (2)	0.061 (2)	0.060 (2)	0.0124 (17)	0.0266 (18)	−0.0089 (17)
C17	0.053 (2)	0.073 (2)	0.075 (3)	0.0072 (18)	0.0156 (19)	−0.009 (2)
C18	0.065 (2)	0.057 (2)	0.063 (2)	−0.0105 (18)	0.0105 (18)	−0.0089 (18)
C19	0.0488 (18)	0.0533 (19)	0.059 (2)	0.0015 (15)	0.0220 (16)	−0.0111 (16)
C20	0.148 (4)	0.068 (2)	0.072 (3)	0.060 (3)	0.040 (3)	0.029 (2)
C21	0.0366 (16)	0.0423 (16)	0.0377 (16)	−0.0074 (13)	0.0080 (12)	−0.0005 (13)

Co1—N6i	2.074 (2)	C4—H4	0.9500
Co1—N6	2.074 (2)	C5—C6	1.384 (4)
Co1—O3	2.134 (2)	C5—H5	0.9500
Co1—O3i	2.134 (2)	C6—C7	1.499 (4)
Co1—N4i	2.162 (2)	C8—C9	1.513 (4)
Co1—N4	2.162 (2)	C8—H8A	0.9900
S1—C21	1.627 (3)	C8—H8B	0.9900
O1—C1	1.224 (3)	C9—C10	1.371 (4)
O2—C7	1.234 (3)	C9—C13	1.373 (4)
O3—C20	1.399 (4)	C10—H10	0.9500
O3—H1	0.76 (3)	C11—C12	1.369 (4)
N1—C2	1.333 (3)	C11—H11	0.9500
N1—C6	1.341 (3)	C12—C13	1.369 (4)
N2—C1	1.336 (4)	C12—H12	0.9500
N2—C8	1.447 (4)	C13—H13	0.9500
N2—H2A	0.8800	C14—C15	1.507 (4)
N3—C7	1.325 (3)	C14—H14A	0.9900
N3—C14	1.456 (4)	C14—H14B	0.9900
N3—H3A	0.8800	C15—C19	1.372 (4)
N4—C11	1.334 (3)	C15—C16	1.377 (4)
N4—C10	1.344 (3)	C16—C17	1.366 (5)
N5—C18	1.327 (4)	C16—H16	0.9500
N5—C19	1.335 (4)	C17—C18	1.372 (5)
N6—C21	1.158 (3)	C17—H17	0.9500
C1—C2	1.498 (4)	C18—H18	0.9500
C2—C3	1.393 (4)	C19—H19	0.9500
C3—C4	1.375 (4)	C20—H20A	0.9800
C3—H3	0.9500	C20—H20B	0.9800
C4—C5	1.377 (4)	C20—H20C	0.9800
N6i—Co1—N6	180.00 (9)	N3—C7—C6	116.4 (2)
N6i—Co1—O3	88.41 (9)	N2—C8—C9	114.9 (2)
N6—Co1—O3	91.59 (9)	N2—C8—H8A	108.6
N6i—Co1—O3i	91.59 (9)	C9—C8—H8A	108.6
N6—Co1—O3i	88.41 (9)	N2—C8—H8B	108.6
O3—Co1—O3i	180.0	C9—C8—H8B	108.6
N6i—Co1—N4i	90.80 (9)	H8A—C8—H8B	107.5
N6—Co1—N4i	89.20 (9)	C10—C9—C13	117.6 (3)
O3—Co1—N4i	89.60 (9)	C10—C9—C8	121.8 (3)
O3i—Co1—N4i	90.40 (9)	C13—C9—C8	120.4 (3)
N6i—Co1—N4	89.20 (9)	N4—C10—C9	123.9 (3)
N6—Co1—N4	90.80 (9)	N4—C10—H10	118.1
O3—Co1—N4	90.40 (9)	C9—C10—H10	118.1
O3i—Co1—N4	89.60 (9)	N4—C11—C12	122.0 (3)
N4i—Co1—N4	180.0	N4—C11—H11	119.0
C20—O3—Co1	129.8 (2)	C12—C11—H11	119.0
C20—O3—H1	111 (2)	C13—C12—C11	119.9 (3)
Co1—O3—H1	118 (2)	C13—C12—H12	120.1
C2—N1—C6	117.7 (2)	C11—C12—H12	120.1
C1—N2—C8	123.2 (3)	C12—C13—C9	119.2 (3)
C1—N2—H2A	118.4	C12—C13—H13	120.4
C8—N2—H2A	118.4	C9—C13—H13	120.4
C7—N3—C14	121.5 (2)	N3—C14—C15	113.6 (2)
C7—N3—H3A	119.2	N3—C14—H14A	108.9
C14—N3—H3A	119.2	C15—C14—H14A	108.9
C11—N4—C10	117.3 (2)	N3—C14—H14B	108.9
C11—N4—Co1	123.2 (2)	C15—C14—H14B	108.9
C10—N4—Co1	119.40 (18)	H14A—C14—H14B	107.7
C18—N5—C19	116.7 (3)	C19—C15—C16	117.1 (3)
C21—N6—Co1	154.7 (2)	C19—C15—C14	120.2 (3)
O1—C1—N2	123.5 (3)	C16—C15—C14	122.7 (3)
O1—C1—C2	121.3 (3)	C17—C16—C15	119.4 (3)
N2—C1—C2	115.2 (3)	C17—C16—H16	120.3
N1—C2—C3	122.9 (3)	C15—C16—H16	120.3
N1—C2—C1	116.7 (3)	C16—C17—C18	119.2 (3)
C3—C2—C1	120.5 (3)	C16—C17—H17	120.4
C4—C3—C2	118.5 (3)	C18—C17—H17	120.4
C4—C3—H3	120.7	N5—C18—C17	122.9 (3)
C2—C3—H3	120.7	N5—C18—H18	118.5
C3—C4—C5	119.3 (3)	C17—C18—H18	118.5
C3—C4—H4	120.4	N5—C19—C15	124.6 (3)
C5—C4—H4	120.4	N5—C19—H19	117.7
C4—C5—C6	118.7 (3)	C15—C19—H19	117.7
C4—C5—H5	120.7	O3—C20—H20A	109.5
C6—C5—H5	120.7	O3—C20—H20B	109.5
N1—C6—C5	122.9 (3)	H20A—C20—H20B	109.5
N1—C6—C7	116.9 (2)	O3—C20—H20C	109.5
C5—C6—C7	120.2 (3)	H20A—C20—H20C	109.5
O2—C7—N3	122.6 (3)	H20B—C20—H20C	109.5
O2—C7—C6	121.0 (3)	N6—C21—S1	179.4 (3)
N6i—Co1—O3—C20	167.7 (3)	C4—C5—C6—C7	179.8 (3)
N6—Co1—O3—C20	−12.3 (3)	C14—N3—C7—O2	−1.4 (4)
N4i—Co1—O3—C20	76.9 (3)	C14—N3—C7—C6	178.5 (2)
N4—Co1—O3—C20	−103.1 (3)	N1—C6—C7—O2	−173.0 (3)
N6i—Co1—N4—C11	57.5 (2)	C5—C6—C7—O2	6.5 (4)
N6—Co1—N4—C11	−122.5 (2)	N1—C6—C7—N3	7.2 (4)
O3—Co1—N4—C11	−30.9 (2)	C5—C6—C7—N3	−173.4 (3)
O3i—Co1—N4—C11	149.1 (2)	C1—N2—C8—C9	94.9 (3)
N6i—Co1—N4—C10	−119.7 (2)	N2—C8—C9—C10	−22.9 (4)
N6—Co1—N4—C10	60.3 (2)	N2—C8—C9—C13	160.6 (3)
O3—Co1—N4—C10	151.9 (2)	C11—N4—C10—C9	−0.5 (4)
O3i—Co1—N4—C10	−28.1 (2)	Co1—N4—C10—C9	176.9 (2)
O3—Co1—N6—C21	12.0 (5)	C13—C9—C10—N4	1.7 (4)
O3i—Co1—N6—C21	−168.0 (5)	C8—C9—C10—N4	−174.9 (3)
N4i—Co1—N6—C21	−77.6 (5)	C10—N4—C11—C12	−1.2 (4)
N4—Co1—N6—C21	102.4 (5)	Co1—N4—C11—C12	−178.4 (2)
C8—N2—C1—O1	−2.3 (4)	N4—C11—C12—C13	1.5 (5)
C8—N2—C1—C2	177.9 (2)	C11—C12—C13—C9	−0.2 (5)
C6—N1—C2—C3	1.8 (4)	C10—C9—C13—C12	−1.4 (5)
C6—N1—C2—C1	−176.7 (2)	C8—C9—C13—C12	175.3 (3)
O1—C1—C2—N1	173.9 (3)	C7—N3—C14—C15	74.6 (4)
N2—C1—C2—N1	−6.3 (4)	N3—C14—C15—C19	−133.0 (3)
O1—C1—C2—C3	−4.7 (4)	N3—C14—C15—C16	49.6 (4)
N2—C1—C2—C3	175.0 (3)	C19—C15—C16—C17	0.5 (5)
N1—C2—C3—C4	−2.2 (4)	C14—C15—C16—C17	178.0 (3)
C1—C2—C3—C4	176.3 (3)	C15—C16—C17—C18	0.0 (5)
C2—C3—C4—C5	1.0 (5)	C19—N5—C18—C17	0.2 (5)
C3—C4—C5—C6	0.4 (5)	C16—C17—C18—N5	−0.3 (5)
C2—N1—C6—C5	−0.3 (4)	C18—N5—C19—C15	0.3 (5)
C2—N1—C6—C7	179.1 (2)	C16—C15—C19—N5	−0.6 (5)
C4—C5—C6—N1	−0.8 (4)	C14—C15—C19—N5	−178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N5ii	0.88	2.18	2.980 (3)	151
O3—H1···O2iii	0.76 (3)	1.94 (3)	2.679 (3)	163 (3)

Table 1

Selected bond lengths (Å)

Co1—N6	2.074 (2)
Co1—O3	2.134 (2)
Co1—N4	2.162 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N5i	0.88	2.18	2.980 (3)	151
O3—H1⋯O2ii	0.76 (3)	1.94 (3)	2.679 (3)	163 (3)

Symmetry codes: (i) ; (ii) .