Bis(2-amino­pyridine-κN1)bis­(benzoato-κO)cobalt(II)

Zhong, D.-C.; Guo, G.-Q.; Zuo, X.-H.; Deng, J.-H.; Yuan, L.; Zhu, R.-H.

doi:10.1107/S1600536807063933

Bis(2-aminopyridine-N¹)bis(benzoato-O)cobalt(II)

D.-C. Zhong, G.-Q. Guo, X.-H. Zuo, J.-H. Deng, L. Yuan and R.-H. Zhu

In the title compound, [Co(C₇H₅O₂)₂(C₅H₆N₂)₂], the Co^II atom is hexacoordinated by four O atoms from two benzoate anions, and two N atoms from two 2-aminopyridine molecules, resulting in a distorted octahedral geometry. Both benzoate anions act as bidentate ligands and both 2-aminopyridine molecules are coordinated to the metal through their pyridyl N atoms. The crystal packing is stabilized by intermolecular N-H

O hydrogen bonds, C-H

, and

stacking interactions involving benzoate anions and 2-aminopyridine molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807063933/kp2149sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807063933/kp2149Isup2.hkl Contains datablock I

CCDC reference: 674206

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.034
wR factor = 0.092
Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Co1    -   O1      ..      37.55 su

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O4      ..       7.20 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        357

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Comment top

In recent years the study of crystal structures and properties of cobalt complexes based on carboxyl ligand, owing to their novel geometries and magnetic behaviours, have attracted chemists (Tan et al., 2003; Zheng et al., 2004; Wang et al., 2004; Shi et al., 2004) to explore their use. The structures of the mixed ligand complexes containing benzoate as the most simple aromatic carboxyl compoud with well antibacterial activity and 2-aminopyridine reported by (Kozlevčar et al., 2001; Zhu, Usman et al., 2003; Zhu, Shao et al., 2004). Herein, we report the synthesis and crystal structure of mixed ligands cobalt(II) complex.

The stucture of the title compound (I) is isostructural with the nickel (I) complex (Zhu, Shao et al., 2003) with the Co^II atom hexa-coordinated by four O atoms of two benzoato anions, and two independent pyridine N atoms from two 2-aminopyridine molecules in distorted octahedral geometry (Fig. 1). The Co—N bond lengths of 2.1030 (14) Å and 2.1054 (14) Å, the Co—O distances ranging from 2.0363 (13) to 2.4016 (15) Å, are in the normal range. The close carboxylato distances O1—C8 and O2—C8, 1.260 (2) Å and 1.250 (2) Å, O3—C1 and O4—C1, 1.241 (2) Å and 1.274 (2) Å reveal the bidentate benzoato function. The molecules are held together by intramolecular and intermolecular hydrogen bonds, C—H···π and π–π stacking interactions generating three-dimensional supramolecular network.The amide N2 and N4 donate H atoms to the carboxyl O atoms O1and O4 in intramolecular N2—H2A···O1 and N4—H4A···O4 hydrogen bonds. The N2 and N4 also donate H atoms to O2 and O3 to form intermolecular N2—H2B···O2 and N4—H4B···O3 hydrogen bonds. Intermolecular C—H···π interation is pronounced in this crystal structure involving methyl group C13 of the benzoato and the pyridyl rings N1→C24, with the distance 2.95 Å between the methyl hydrogen and the centroid of the nearest aromatic ring. In addition, π–π stacking interactions are also observed; the distance between centroids of the pyridyl ring N3→C19 and the aromatic ring C2→C7 is 3.7145 (16) Å (Table 1, Fig. 2).

Related literature top

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 top

The reagents available commercially were used without further purification. Co(NO₃)₂.6H₂O (0.5 mmol), benzoate sodium (1 mmol) and 2-aminopyridine (1 mmol) were mixed in solution containing 8 ml of ethanol and 8 ml of water. After stirring 1.5 h, the mixture was placed in 25 ml Teflon-lined reactor and heated at 383 K in an oven for 7 days. The resulting solution was filtered and the filtrate was allowed to stay at ambience temperature. Well shaped purple crystals suitable for X-rays diffraction were obtained after two weeks. Yield: 78%.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 1997b).

Figures top

	Fig. 1. The structure of (I) with the 30% probability displacement ellipsoids and the atom-labeling scheme.
	Fig. 2. Three-dimensional supramolecular network constructed by hydrogen bonding (dashed lines) and C—H···π, π-π interactions.

Bis(2-aminopyridine-κN¹)bis(benzoato-κO)cobalt(II) top

Crystal data top

[Co(C₇H₅O₂)₂(C₅H₆N₂)₂]	F(000) = 1012
M_r = 489.39	D_x = 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 = 2.4–27.2°
b = 11.3787 (12) Å	µ = 0.79 mm⁻¹
c = 22.451 (2) Å	T = 296 K
β = 96.765 (1)°	Block, purple
V = 2288.9 (4) Å³	0.36 × 0.28 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5288 independent reflections
Radiation source: fine-focus sealed tube	4198 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 27.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.770, T_max = 0.835	k = −14→14
19674 measured reflections	l = −29→25

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0416P)² + 0.6259P] where P = (F_o² + 2F_c²)/3
5288 reflections	(Δ/σ)_max = 0.050
298 parameters	Δρ_max = 0.32 e Å⁻³
357 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

[Co(C₇H₅O₂)₂(C₅H₆N₂)₂]	V = 2288.9 (4) Å³
M_r = 489.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0230 (9) Å	µ = 0.79 mm⁻¹
b = 11.3787 (12) Å	T = 296 K
c = 22.451 (2) Å	0.36 × 0.28 × 0.22 mm
β = 96.765 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5288 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4198 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.835	R_int = 0.027
19674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	357 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 0.32 e Å⁻³
5288 reflections	Δρ_min = −0.27 e Å⁻³
298 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	[Co(C₇H₅O₂)₂(C₅H₆N₂)₂]
M_r	489.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	9.0230 (9), 11.3787 (12), 22.451 (2)
β (°)	96.765 (1)
V (Å³)	2288.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.36 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.770, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	19674, 5288, 4198
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.092, 1.05
No. of reflections	5288
No. of parameters	298
No. of restraints	357
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.27

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top

Co1—O4	2.0364 (15)	Co1—O3	2.4016 (17)
Co1—N3	2.1033 (16)	O1—C8	1.260 (3)
Co1—N1	2.1050 (16)	O2—C8	1.249 (3)
Co1—O1	2.1426 (18)	O3—C1	1.240 (2)
Co1—O2	2.2340 (17)	O4—C1	1.274 (2)

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

Hydrogen-bond geometry (Å, º) top

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

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

C-H···π interactions (Å, °) top

C—H···Cg^a	H···Cg	C···Cg	γ^b	C—H···Cg
C13—H13···Cg(N1→C24)ⁱⁱⁱ	2.95	3.719 (3)	6.07	141

Notes: Cg^a = centre of gravity of the six-membered ring. γ^b = angle defined by a line connecting centre of gravity of the six-membered ring with H atom and the normal to the six-membered ring. Symmetry code: (iii) -x, 1 - y, -z.

π–π interactions (Å, °) top

π–π contacts	Cg···Cg	α^a(	β^b	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

Notes: α^a = angle between planes of two aromatic rings. β^b = 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.

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Bis(2-amino­pyridine-N1)bis­(benzoato-O)cobalt(II)

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Bis(2-aminopyridine-N¹)bis(benzoato-O)cobalt(II)