Bis(2-amino-pyridine-κN)bis-(benzoato-κO)cobalt(II).

In the title compound, [Co(C(7)H(5)O(2))(2)(C(5)H(6)N(2))(2)], the Co(II) atom is hexa-coordinated by four O atoms from two benzoate anions, and two N atoms from two 2-amino-pyridine mol-ecules, resulting in a distorted octa-hedral geometry. Both benzoate anions act as bidentate ligands and both 2-amino-pyridine mol-ecules are coordinated to the metal through their pyridyl N atoms. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds, C-H⋯π, and π-π stacking inter-actions involving benzoate anions and 2-amino-pyridine mol-ecules.

Related literature

For related literature, see: Benbellat et al. (2006 ▶); Brechin et al. (2000 ▶); Dirnitrou et al. (1995 ▶); Kozlevčar et al. (2001 ▶); Zhu, Shao et al. (2003 ▶); Zhu, Usman et al. (2003 ▶).

Experimental

Crystal data

[Co(C7H5O2)2(C5H6N2)2]

M = 489.39

Monoclinic,

a = 9.0230 (9) Å

b = 11.3787 (12) Å

c = 22.451 (2) Å

β = 96.7650 (10)°

V = 2288.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 296 (2) K

0.36 × 0.28 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.770, T max = 0.835

19674 measured reflections

5288 independent reflections

4198 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.05

5288 reflections

298 parameters

357 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063933/kp2149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063933/kp2149Isup2.hkl

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

[Co(C7H5O2)2(C5H6N2)2]	F000 = 1012
Mr = 489.39	Dx = 1.420 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7256 reflections
a = 9.0230 (9) Å	θ = 2.4–27.2º
b = 11.3787 (12) Å	µ = 0.79 mm−1
c = 22.451 (2) Å	T = 296 (2) K
β = 96.7650 (10)º	Block, purple
V = 2288.9 (4) Å3	0.36 × 0.28 × 0.22 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5288 independent reflections
Radiation source: fine-focus sealed tube	4198 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.027
T = 296(2) K	θmax = 27.7º
phi and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.770, Tmax = 0.835	k = −14→14
19674 measured reflections	l = −29→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.6259P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.050
5288 reflections	Δρmax = 0.32 e Å−3
298 parameters	Δρmin = −0.27 e Å−3
357 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Co1	0.29899 (3)	0.42895 (2)	0.123207 (11)	0.04251 (10)
N1	0.37446 (18)	0.31734 (14)	0.05834 (7)	0.0434 (4)
N2	0.3314 (2)	0.44408 (15)	−0.02241 (8)	0.0520 (4)
H2A	0.2773	0.4869	−0.0019	0.062*
H2B	0.3439	0.4640	−0.0584	0.062*
N3	0.11106 (18)	0.33308 (14)	0.14242 (7)	0.0429 (4)
N4	0.2282 (2)	0.2407 (2)	0.22706 (9)	0.0745 (6)
H4A	0.3108	0.2736	0.2208	0.089*
H4B	0.2254	0.1949	0.2574	0.089*
O1	0.1750 (2)	0.55468 (13)	0.06636 (7)	0.0651 (5)
O2	0.2427 (2)	0.60479 (15)	0.15868 (8)	0.0698 (5)
O3	0.54634 (19)	0.51020 (15)	0.13357 (6)	0.0602 (4)
O4	0.45109 (17)	0.39318 (15)	0.19532 (6)	0.0566 (4)
C1	0.5594 (2)	0.45573 (18)	0.18175 (9)	0.0444 (4)
C2	0.6981 (2)	0.4610 (2)	0.22510 (10)	0.0504 (5)
C3	0.7083 (3)	0.3990 (3)	0.27797 (11)	0.0690 (7)
H3	0.6284	0.3539	0.2875	0.083*
C4	0.8401 (4)	0.4045 (3)	0.31715 (15)	0.0957 (10)
H4	0.8483	0.3637	0.3533	0.115*
C5	0.9565 (4)	0.4697 (4)	0.30237 (19)	0.1039 (11)
H5	1.0446	0.4716	0.3284	0.125*
C6	0.9476 (3)	0.5316 (4)	0.2510 (2)	0.1015 (11)
H6	1.0283	0.5765	0.2421	0.122*
C7	0.8173 (3)	0.5283 (3)	0.21134 (14)	0.0760 (7)
H7	0.8102	0.5710	0.1758	0.091*
C8	0.1784 (2)	0.62950 (18)	0.10788 (10)	0.0520 (5)
C9	0.1044 (2)	0.74580 (18)	0.09538 (10)	0.0499 (5)
C10	0.1555 (3)	0.8438 (2)	0.12792 (12)	0.0667 (6)
H10	0.2364	0.8373	0.1575	0.080*
C11	0.0872 (4)	0.9512 (2)	0.11675 (15)	0.0842 (8)
H11	0.1236	1.0173	0.1381	0.101*
C12	−0.0346 (4)	0.9607 (3)	0.07410 (16)	0.0886 (9)
H12	−0.0813	1.0331	0.0670	0.106*
C13	−0.0872 (4)	0.8644 (3)	0.04219 (15)	0.0880 (8)
H13	−0.1706	0.8709	0.0138	0.106*
C14	−0.0171 (3)	0.7572 (2)	0.05190 (12)	0.0696 (7)
H14	−0.0515	0.6923	0.0292	0.084*
C15	−0.0147 (2)	0.3464 (2)	0.10357 (10)	0.0529 (5)
H15	−0.0106	0.3956	0.0707	0.063*
C16	−0.1465 (3)	0.2924 (2)	0.10970 (12)	0.0634 (6)
H16	−0.2295	0.3033	0.0815	0.076*
C17	−0.1537 (3)	0.2207 (2)	0.15906 (12)	0.0643 (6)
H17	−0.2426	0.1834	0.1648	0.077*
C18	−0.0309 (3)	0.2052 (2)	0.19887 (11)	0.0594 (6)
H18	−0.0353	0.1578	0.2324	0.071*
C19	0.1036 (2)	0.26105 (18)	0.18948 (9)	0.0479 (5)
C20	0.3961 (2)	0.34636 (17)	0.00178 (8)	0.0426 (4)
C21	0.4848 (3)	0.27532 (19)	−0.03144 (10)	0.0532 (5)
H21	0.5028	0.2980	−0.0697	0.064*
C22	0.5438 (3)	0.1739 (2)	−0.00744 (11)	0.0610 (6)
H22	0.6025	0.1268	−0.0291	0.073*
C23	0.5157 (3)	0.1407 (2)	0.05002 (11)	0.0614 (6)
H23	0.5525	0.0704	0.0669	0.074*
C24	0.4331 (3)	0.21426 (19)	0.08048 (10)	0.0548 (5)
H24	0.4156	0.1926	0.1190	0.066*

	U11	U22	U33	U12	U13	U23
Co1	0.04193 (16)	0.05067 (17)	0.03496 (15)	−0.00377 (11)	0.00463 (10)	0.00284 (11)
N1	0.0453 (9)	0.0461 (9)	0.0388 (8)	−0.0058 (7)	0.0051 (7)	0.0010 (7)
N2	0.0644 (11)	0.0542 (10)	0.0393 (9)	0.0026 (8)	0.0141 (8)	0.0041 (7)
N3	0.0430 (9)	0.0459 (9)	0.0404 (8)	−0.0037 (7)	0.0080 (7)	−0.0016 (7)
N4	0.0630 (13)	0.0910 (16)	0.0676 (13)	−0.0130 (11)	0.0000 (10)	0.0383 (12)
O1	0.0964 (13)	0.0450 (8)	0.0594 (10)	−0.0035 (8)	0.0324 (9)	−0.0087 (7)
O2	0.0713 (11)	0.0598 (10)	0.0745 (11)	0.0096 (8)	−0.0071 (9)	−0.0133 (9)
O3	0.0701 (10)	0.0665 (10)	0.0455 (8)	−0.0001 (8)	0.0132 (7)	0.0081 (7)
O4	0.0462 (8)	0.0740 (10)	0.0483 (8)	−0.0136 (7)	0.0003 (6)	0.0080 (7)
C1	0.0448 (11)	0.0493 (10)	0.0399 (10)	0.0008 (8)	0.0088 (8)	−0.0041 (8)
C2	0.0403 (10)	0.0578 (12)	0.0537 (12)	0.0024 (9)	0.0082 (9)	−0.0181 (10)
C3	0.0601 (14)	0.0847 (16)	0.0591 (14)	0.0156 (12)	−0.0058 (11)	−0.0075 (12)
C4	0.083 (2)	0.119 (2)	0.0781 (18)	0.0320 (18)	−0.0214 (16)	−0.0218 (17)
C5	0.0558 (17)	0.136 (3)	0.113 (2)	0.0282 (18)	−0.0207 (17)	−0.062 (2)
C6	0.0519 (15)	0.125 (2)	0.128 (3)	−0.0153 (16)	0.0137 (17)	−0.060 (2)
C7	0.0550 (14)	0.0890 (17)	0.0862 (17)	−0.0142 (13)	0.0174 (13)	−0.0327 (15)
C8	0.0520 (12)	0.0452 (11)	0.0625 (13)	−0.0078 (9)	0.0225 (10)	−0.0096 (10)
C9	0.0507 (12)	0.0462 (10)	0.0556 (12)	−0.0041 (9)	0.0179 (9)	−0.0073 (9)
C10	0.0746 (16)	0.0515 (12)	0.0732 (15)	−0.0025 (11)	0.0052 (12)	−0.0129 (11)
C11	0.108 (2)	0.0492 (13)	0.097 (2)	0.0020 (14)	0.0172 (18)	−0.0177 (13)
C12	0.098 (2)	0.0639 (16)	0.106 (2)	0.0221 (15)	0.0193 (18)	0.0063 (16)
C13	0.0807 (19)	0.0802 (19)	0.100 (2)	0.0087 (15)	−0.0046 (16)	0.0101 (16)
C14	0.0707 (16)	0.0606 (14)	0.0754 (16)	−0.0063 (12)	−0.0003 (13)	−0.0067 (12)
C15	0.0504 (12)	0.0540 (12)	0.0530 (12)	−0.0063 (9)	0.0013 (9)	0.0007 (10)
C16	0.0467 (12)	0.0608 (13)	0.0809 (16)	−0.0081 (10)	−0.0001 (11)	−0.0041 (12)
C17	0.0498 (13)	0.0555 (13)	0.0900 (17)	−0.0121 (10)	0.0191 (12)	−0.0067 (12)
C18	0.0655 (14)	0.0483 (11)	0.0686 (14)	−0.0083 (10)	0.0257 (12)	0.0039 (10)
C19	0.0511 (11)	0.0451 (10)	0.0495 (11)	−0.0017 (9)	0.0146 (9)	−0.0001 (9)
C20	0.0412 (10)	0.0454 (10)	0.0412 (9)	−0.0104 (8)	0.0050 (8)	−0.0040 (8)
C21	0.0579 (13)	0.0544 (12)	0.0493 (11)	−0.0079 (10)	0.0151 (9)	−0.0079 (9)
C22	0.0602 (14)	0.0558 (13)	0.0685 (14)	−0.0024 (10)	0.0141 (11)	−0.0156 (11)
C23	0.0654 (14)	0.0489 (12)	0.0683 (14)	0.0016 (10)	0.0015 (11)	−0.0004 (11)
C24	0.0614 (13)	0.0525 (12)	0.0503 (12)	−0.0043 (10)	0.0058 (10)	0.0039 (10)

Co1—O4	2.0364 (15)	C6—H6	0.9300
Co1—N3	2.1033 (16)	C7—H7	0.9300
Co1—N1	2.1050 (16)	C8—C9	1.494 (3)
Co1—O1	2.1426 (18)	C9—C10	1.383 (3)
Co1—O2	2.2340 (17)	C9—C14	1.386 (3)
Co1—O3	2.4016 (17)	C10—C11	1.378 (4)
N1—C20	1.348 (2)	C10—H10	0.9300
N1—C24	1.357 (3)	C11—C12	1.374 (4)
N2—C20	1.341 (3)	C11—H11	0.9300
N2—H2A	0.8600	C12—C13	1.364 (5)
N2—H2B	0.8600	C12—H12	0.9300
N3—C19	1.345 (3)	C13—C14	1.379 (4)
N3—C15	1.356 (3)	C13—H13	0.9300
N4—C19	1.344 (3)	C14—H14	0.9300
N4—H4A	0.8600	C15—C16	1.360 (3)
N4—H4B	0.8600	C15—H15	0.9300
O1—C8	1.260 (3)	C16—C17	1.384 (4)
O2—C8	1.249 (3)	C16—H16	0.9300
O3—C1	1.240 (2)	C17—C18	1.350 (4)
O4—C1	1.274 (2)	C17—H17	0.9300
C1—C2	1.493 (3)	C18—C19	1.408 (3)
C2—C3	1.375 (3)	C18—H18	0.9300
C2—C7	1.385 (3)	C20—C21	1.411 (3)
C3—C4	1.395 (4)	C21—C22	1.355 (3)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.359 (6)	C22—C23	1.396 (3)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.345 (5)	C23—C24	1.358 (3)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.389 (4)	C24—H24	0.9300
O4—Co1—N3	102.55 (6)	O2—C8—O1	119.5 (2)
O4—Co1—N1	100.77 (7)	O2—C8—C9	121.34 (19)
N3—Co1—N1	99.40 (6)	O1—C8—C9	119.2 (2)
O4—Co1—O1	149.63 (7)	C10—C9—C14	118.9 (2)
N3—Co1—O1	95.25 (7)	C10—C9—C8	120.1 (2)
N1—Co1—O1	100.34 (6)	C14—C9—C8	121.0 (2)
O4—Co1—O2	93.20 (7)	C11—C10—C9	120.3 (3)
N3—Co1—O2	99.72 (7)	C11—C10—H10	119.8
N1—Co1—O2	153.21 (7)	C9—C10—H10	119.8
O1—Co1—O2	59.31 (6)	C12—C11—C10	120.1 (3)
O4—Co1—O3	57.88 (5)	C12—C11—H11	120.0
N3—Co1—O3	160.43 (6)	C10—C11—H11	120.0
N1—Co1—O3	85.79 (6)	C13—C12—C11	120.2 (3)
O1—Co1—O3	102.40 (6)	C13—C12—H12	119.9
O2—Co1—O3	82.44 (6)	C11—C12—H12	119.9
C20—N1—C24	117.60 (18)	C12—C13—C14	120.2 (3)
C20—N1—Co1	126.75 (13)	C12—C13—H13	119.9
C24—N1—Co1	114.33 (13)	C14—C13—H13	119.9
C20—N2—H2A	120.0	C13—C14—C9	120.3 (3)
C20—N2—H2B	120.0	C13—C14—H14	119.8
H2A—N2—H2B	120.0	C9—C14—H14	119.8
C19—N3—C15	117.26 (17)	N3—C15—C16	124.0 (2)
C19—N3—Co1	126.38 (14)	N3—C15—H15	118.0
C15—N3—Co1	116.35 (13)	C16—C15—H15	118.0
C19—N4—H4A	120.0	C15—C16—C17	118.2 (2)
C19—N4—H4B	120.0	C15—C16—H16	120.9
H4A—N4—H4B	120.0	C17—C16—H16	120.9
C8—O1—Co1	92.57 (15)	C18—C17—C16	119.7 (2)
C8—O2—Co1	88.66 (13)	C18—C17—H17	120.2
C1—O3—Co1	83.32 (13)	C16—C17—H17	120.2
C1—O4—Co1	99.33 (12)	C17—C18—C19	119.8 (2)
O3—C1—O4	119.41 (19)	C17—C18—H18	120.1
O3—C1—C2	122.31 (19)	C19—C18—H18	120.1
O4—C1—C2	118.28 (18)	N4—C19—N3	118.84 (18)
C3—C2—C7	120.1 (2)	N4—C19—C18	120.1 (2)
C3—C2—C1	120.5 (2)	N3—C19—C18	121.1 (2)
C7—C2—C1	119.4 (2)	N2—C20—N1	118.69 (18)
C2—C3—C4	119.1 (3)	N2—C20—C21	120.54 (18)
C2—C3—H3	120.4	N1—C20—C21	120.77 (19)
C4—C3—H3	120.4	C22—C21—C20	119.9 (2)
C5—C4—C3	119.8 (4)	C22—C21—H21	120.1
C5—C4—H4	120.1	C20—C21—H21	120.1
C3—C4—H4	120.1	C21—C22—C23	119.5 (2)
C4—C5—C6	121.7 (3)	C21—C22—H22	120.3
C4—C5—H5	119.1	C23—C22—H22	120.3
C6—C5—H5	119.2	C24—C23—C22	118.0 (2)
C5—C6—C7	119.7 (3)	C24—C23—H23	121.0
C5—C6—H6	120.1	C22—C23—H23	121.0
C7—C6—H6	120.1	C23—C24—N1	124.2 (2)
C2—C7—C6	119.5 (3)	C23—C24—H24	117.9
C2—C7—H7	120.2	N1—C24—H24	117.9
C6—C7—H7	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	2.03	2.866 (2)	163
N2—H2B···O3i	0.86	2.07	2.891 (2)	158
N4—H4A···O4	0.86	1.99	2.810 (2)	160
N4—H4B···O2ii	0.86	2.14	2.980 (2)	167

C—H···Cga	H···Cg	C···Cg	γb	C—H···Cg
C13—H13···Cg(N1→C24)iii	2.95	3.719 (3)	6.07	141

π–π contacts	Cg···Cg	αa(	βb	Cg···Plane
Cg(N3→C19)···Cg(C2→C7)iv	3.7145 (16)	6.30	16.02	3.535
Cg(C2→C7)···Cg(N3→C19)v	3.7145 (16)	6.30	17.87	3.570

Co1—O4	2.0364 (15)
Co1—N3	2.1033 (16)
Co1—N1	2.1050 (16)
Co1—O1	2.1426 (18)
Co1—O2	2.2340 (17)
Co1—O3	2.4016 (17)

O4—Co1—N3	102.55 (6)
O4—Co1—N1	100.77 (7)
N3—Co1—N1	99.40 (6)
N3—Co1—O1	95.25 (7)
N1—Co1—O1	100.34 (6)
O4—Co1—O2	93.20 (7)
N3—Co1—O2	99.72 (7)
N1—Co1—O2	153.21 (7)
O1—Co1—O2	59.31 (6)
O4—Co1—O3	57.88 (5)
N3—Co1—O3	160.43 (6)
N1—Co1—O3	85.79 (6)
O1—Co1—O3	102.40 (6)
O2—Co1—O3	82.44 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	2.03	2.866 (2)	163
N2—H2B⋯O3i	0.86	2.07	2.891 (2)	158
N4—H4A⋯O4	0.86	1.99	2.810 (2)	160
N4—H4B⋯O2ii	0.86	2.14	2.980 (2)	167
C13—H13⋯Cg1iii	0.93	2.95	3.719 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) −x, 1 − y, −z. Cg1 is the centroid of the N1/C20–C24 ring.

Table 3

π–π Interactions (Å, °)

π–π Contacts	Cg⋯Cg	αa	βb	Cg⋯Plane
Cg(N3→C19)⋯Cg(C2→C7)iv	3.7145 (16)	6.3	16.0	3.535
Cg(C2→C7)⋯Cg(N3→C19)v	3.7145 (16)	6.3	17.9	3.570

Notes: αa = angle between planes of two aromatic rings. βb = angle between Cg⋯Cg line and normal to the plane of the first aromatic ring. Symmetry codes: (iv) −1 + x, y, z; (v) 1 + x, y, z.