Tris(1H-benzimidazole-κN3)(oxydiacetato-κ3O,O′,O′′)cobalt(II)

Cao, L.; Xu, D.-J.

doi:10.1107/S1600536805030126

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Tris(1H-benzimidazole-κN³)(oxydiacetato-κ³O,O′,O′′)cobalt(II)

L. Cao and D.-J. Xu

In the title complex, [Co(C₄H₄O₅)(C₇H₆N₂)₃], one tridentate oxydiacetate dianion and three benzimidazole molecules coordinate to the Co^II cation, resulting in a distorted octahedral geometry. The oxydiacetate ligand chelates to the Co^II cation with a facial configuration and the Co—O(ether) bond distance is longer than the average Co—O(carboxyl) bond distance by 0.185 (3) Å. A network of N—H

O hydrogen bonds helps to establish the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030126/hb6272sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030126/hb6272Isup2.hkl Contains datablock I

CCDC reference: 287585

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.041
wR factor = 0.114
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   O3      ..       5.80 su

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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

Comment top

Several reported X-ray structures of metal complexes incorporating the benzimidazole (C₇H₆N₂; BZIM) ligand have shown the existence of π–π stacking between neighbouring aromatic rings in these crystals (Chen et al., 2003; Liu & Xu, 2004; Bukowska-Strzyżewska & Tosik, 1983). As part of our ongoing investigations of the nature of π–π stacking (Li et al., 2005), the title BZIM/ODA (ODA is the oxydiacetate dianion, C₄H₄O₅²⁻) complex of Co^II, (I), has been prepared in our laboratory, and its structure is presented here.

The molecular structure of (I) is illustrated in Fig. 1. The combination of three BZIM ligands and a tridentate chelating ODA ligand results in a distorted octahedral coordination for the Co^II cation (Table 1). The facial configuration of the ODA anion in (I) differs from the meridional configuration found in most Co complexes with a chelating ODA ligand (CSD, Version?, November 2004 update; Allen, 2002), but agrees with that found in diaqua(nitrobenzimidazole)(ODA)cobalt(II) (Zhang et al., 2005). It is notable that the Co—O(ether) bond is significantly longer than the Co—O(carboxyl) bonds in (I).

As shown in the unit-cell packing diagram (Fig. 2), the uncoordinated ODA carboxyl atoms, O2 and O5, form links with the BZIM ligands of neighbouring complexes by accepting N—H···O hydrogen bonds (Table 2), which results in a long centroid-to-centroid separation (> 5 Å) for the latter species. Thus, no π–π stacking occurs between parallel BZIM ligands in the crystal of (I).

Experimental top

An aqueous solution (15 ml) solution of CoCl₂·6H₂O (1 mmol), H₂ODA (1 mmol) and Na₂CO₃ (1 mmol) was mixed with an ethanol solution (5 ml) of BZIM (2 mmol). The solution was refluxed for 5 h and then filtered. Red single crystals of (I) were obtained after 2 d.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
	Fig. 2. A unit-cell packing diagram for (I). Dashed lines indicate intermolecular hydrogen bonds. [Symmetry codes: (i) 1 − x,-1/2 + y,1/2 − z; (iii) x,3/2 − y,1/2 + z.]

Tris(1H-benzimidazole-κN³)(oxydiacetate-κ³O,O',O'')cobalt(II) top

Crystal data top

[Co(C₇H₆N₂)₃(C₄H₄O₅)]	F(000) = 1124
M_r = 545.42	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11165 reflections
a = 12.2152 (4) Å	θ = 2.3–26.5°
b = 10.3120 (2) Å	µ = 0.75 mm⁻¹
c = 19.3617 (4) Å	T = 295 K
β = 91.257 (1)°	Rod, red
V = 2438.27 (11) Å³	0.26 × 0.09 × 0.06 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4587 independent reflections
Radiation source: fine-focus sealed tube	3430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 10.00 pixels mm^-1	θ_max = 25.6°, θ_min = 1.7°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
T_min = 0.918, T_max = 0.955	l = −23→23
19382 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.066P)²] where P = (F_o² + 2F_c²)/3
4587 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Co(C₇H₆N₂)₃(C₄H₄O₅)]	V = 2438.27 (11) Å³
M_r = 545.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.2152 (4) Å	µ = 0.75 mm⁻¹
b = 10.3120 (2) Å	T = 295 K
c = 19.3617 (4) Å	0.26 × 0.09 × 0.06 mm
β = 91.257 (1)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4587 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3430 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.955	R_int = 0.048
19382 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.09	Δρ_max = 0.62 e Å⁻³
4587 reflections	Δρ_min = −0.56 e Å⁻³
334 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
Co	0.75191 (3)	0.73907 (3)	0.222358 (18)	0.02765 (13)
N11	0.4219 (2)	0.6259 (2)	0.18774 (14)	0.0437 (7)
H11	0.3701	0.5709	0.1937	0.052*
N13	0.58625 (19)	0.7168 (2)	0.19689 (12)	0.0321 (5)
N21	0.7815 (2)	0.3249 (2)	0.23005 (14)	0.0433 (7)
H21	0.7729	0.2560	0.2543	0.052*
N23	0.7845 (2)	0.5348 (2)	0.20285 (12)	0.0334 (6)
N31	0.7981 (2)	0.7007 (3)	0.44110 (13)	0.0420 (6)
H31	0.8402	0.6847	0.4763	0.050*
N33	0.7412 (2)	0.7127 (2)	0.33135 (12)	0.0345 (6)
O1	0.79423 (18)	0.7951 (2)	0.12553 (10)	0.0400 (5)
O2	0.9283 (2)	0.8536 (3)	0.05549 (11)	0.0605 (7)
O3	0.92906 (16)	0.80034 (18)	0.23821 (9)	0.0326 (5)
O4	0.73913 (16)	0.93931 (18)	0.24781 (11)	0.0349 (5)
O5	0.82350 (19)	1.09993 (19)	0.30342 (13)	0.0510 (6)
C1	0.8924 (3)	0.8233 (3)	0.11288 (15)	0.0371 (7)
C2	0.9762 (3)	0.8126 (3)	0.17100 (15)	0.0427 (8)
H2A	1.0222	0.7377	0.1628	0.051*
H2B	1.0226	0.8889	0.1707	0.051*
C3	0.9298 (2)	0.9180 (3)	0.27781 (16)	0.0381 (7)
H3A	0.9868	0.9743	0.2608	0.046*
H3B	0.9481	0.8973	0.3255	0.046*
C4	0.8216 (2)	0.9914 (3)	0.27536 (15)	0.0325 (7)
C12	0.5229 (3)	0.6186 (3)	0.21420 (16)	0.0386 (7)
H12	0.5468	0.5507	0.2423	0.046*
C14	0.5416 (3)	0.9138 (3)	0.12418 (15)	0.0409 (7)
H14	0.6095	0.9539	0.1294	0.049*
C15	0.4581 (3)	0.9685 (3)	0.08430 (17)	0.0529 (9)
H15	0.4697	1.0482	0.0632	0.064*
C16	0.3572 (3)	0.9070 (4)	0.07491 (18)	0.0594 (11)
H16	0.3044	0.9451	0.0461	0.071*
C17	0.3334 (3)	0.7915 (4)	0.10705 (19)	0.0543 (9)
H17	0.2658	0.7513	0.1010	0.065*
C18	0.4150 (3)	0.7385 (3)	0.14868 (16)	0.0395 (7)
C19	0.5192 (2)	0.7966 (3)	0.15585 (14)	0.0322 (6)
C22	0.7659 (3)	0.4472 (3)	0.25106 (17)	0.0384 (7)
H22	0.7441	0.4684	0.2954	0.046*
C24	0.8444 (3)	0.4992 (4)	0.07905 (17)	0.0523 (9)
H24	0.8442	0.5859	0.0658	0.063*
C25	0.8743 (4)	0.4013 (4)	0.0339 (2)	0.0709 (12)
H25	0.8953	0.4238	−0.0104	0.085*
C26	0.8740 (4)	0.2702 (4)	0.0525 (2)	0.0716 (12)
H26	0.8955	0.2080	0.0208	0.086*
C27	0.8425 (3)	0.2324 (3)	0.1167 (2)	0.0587 (10)
H27	0.8403	0.1453	0.1291	0.070*
C28	0.8138 (3)	0.3298 (3)	0.16284 (17)	0.0417 (8)
C29	0.8150 (2)	0.4617 (3)	0.14489 (15)	0.0357 (7)
C32	0.8211 (3)	0.6793 (3)	0.37488 (15)	0.0399 (7)
H32	0.8871	0.6442	0.3608	0.048*
C34	0.5556 (3)	0.8102 (3)	0.35706 (16)	0.0418 (8)
H34	0.5310	0.8170	0.3114	0.050*
C35	0.4904 (3)	0.8483 (3)	0.41094 (17)	0.0490 (9)
H35	0.4206	0.8806	0.4013	0.059*
C36	0.5276 (3)	0.8392 (3)	0.47969 (17)	0.0501 (9)
H36	0.4818	0.8654	0.5148	0.060*
C37	0.6292 (3)	0.7929 (3)	0.49633 (16)	0.0457 (8)
H37	0.6539	0.7880	0.5420	0.055*
C38	0.6943 (3)	0.7534 (3)	0.44255 (15)	0.0373 (7)
C39	0.6587 (3)	0.7614 (3)	0.37345 (14)	0.0337 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.0265 (2)	0.0297 (2)	0.0267 (2)	0.00020 (16)	−0.00089 (15)	−0.00012 (16)
N11	0.0269 (15)	0.0422 (14)	0.0621 (18)	−0.0067 (11)	0.0023 (13)	−0.0074 (13)
N13	0.0290 (14)	0.0342 (12)	0.0330 (13)	−0.0017 (10)	−0.0034 (11)	−0.0010 (10)
N21	0.0485 (18)	0.0311 (13)	0.0503 (16)	0.0041 (11)	−0.0011 (13)	0.0027 (12)
N23	0.0332 (15)	0.0346 (13)	0.0323 (13)	0.0045 (10)	−0.0010 (11)	−0.0025 (11)
N31	0.0422 (17)	0.0553 (15)	0.0284 (13)	−0.0050 (13)	−0.0043 (12)	0.0004 (12)
N33	0.0406 (16)	0.0353 (13)	0.0278 (12)	0.0006 (11)	0.0008 (11)	−0.0002 (10)
O1	0.0326 (13)	0.0575 (13)	0.0298 (11)	−0.0038 (10)	−0.0014 (9)	0.0049 (10)
O2	0.0486 (16)	0.102 (2)	0.0316 (12)	−0.0130 (14)	0.0053 (11)	0.0102 (12)
O3	0.0298 (12)	0.0380 (10)	0.0299 (10)	0.0054 (8)	−0.0006 (9)	−0.0019 (9)
O4	0.0252 (12)	0.0340 (10)	0.0454 (12)	0.0028 (8)	−0.0022 (9)	−0.0015 (9)
O5	0.0457 (15)	0.0311 (11)	0.0756 (17)	0.0034 (10)	−0.0099 (12)	−0.0118 (11)
C1	0.036 (2)	0.0437 (17)	0.0316 (16)	0.0031 (14)	0.0014 (14)	0.0007 (13)
C2	0.0288 (18)	0.064 (2)	0.0351 (16)	0.0062 (15)	0.0050 (14)	0.0002 (15)
C3	0.0274 (17)	0.0404 (16)	0.0462 (19)	−0.0009 (13)	−0.0038 (14)	−0.0077 (14)
C4	0.0307 (17)	0.0295 (14)	0.0372 (16)	−0.0006 (12)	0.0000 (13)	0.0047 (13)
C12	0.0312 (18)	0.0348 (15)	0.0498 (19)	−0.0015 (13)	−0.0001 (14)	0.0010 (14)
C14	0.047 (2)	0.0415 (17)	0.0341 (16)	0.0056 (14)	0.0021 (14)	−0.0018 (14)
C15	0.065 (3)	0.052 (2)	0.0421 (19)	0.0218 (18)	0.0038 (18)	0.0034 (16)
C16	0.055 (3)	0.078 (3)	0.045 (2)	0.034 (2)	−0.0125 (18)	−0.0043 (19)
C17	0.035 (2)	0.073 (2)	0.054 (2)	0.0142 (17)	−0.0082 (17)	−0.0149 (19)
C18	0.0319 (18)	0.0457 (17)	0.0409 (17)	0.0064 (14)	−0.0009 (13)	−0.0103 (14)
C19	0.0312 (17)	0.0365 (15)	0.0289 (15)	0.0028 (12)	0.0002 (12)	−0.0066 (12)
C22	0.0398 (19)	0.0343 (16)	0.0411 (17)	0.0057 (13)	−0.0002 (14)	−0.0017 (14)
C24	0.059 (2)	0.056 (2)	0.0424 (19)	−0.0007 (17)	0.0060 (17)	−0.0077 (16)
C25	0.076 (3)	0.090 (3)	0.047 (2)	−0.004 (2)	0.014 (2)	−0.022 (2)
C26	0.073 (3)	0.071 (3)	0.071 (3)	0.006 (2)	0.008 (2)	−0.036 (2)
C27	0.058 (3)	0.0466 (19)	0.072 (3)	0.0091 (17)	−0.002 (2)	−0.0216 (19)
C28	0.0315 (18)	0.0402 (17)	0.053 (2)	0.0046 (13)	−0.0045 (15)	−0.0111 (15)
C29	0.0270 (17)	0.0418 (16)	0.0382 (17)	0.0035 (12)	−0.0028 (13)	−0.0087 (13)
C32	0.040 (2)	0.0454 (17)	0.0347 (17)	0.0012 (14)	−0.0004 (14)	−0.0020 (14)
C34	0.050 (2)	0.0417 (16)	0.0339 (16)	0.0047 (15)	0.0008 (15)	0.0005 (14)
C35	0.050 (2)	0.0484 (19)	0.048 (2)	0.0103 (16)	0.0073 (17)	−0.0004 (16)
C36	0.060 (3)	0.0481 (18)	0.0424 (19)	−0.0017 (17)	0.0185 (17)	−0.0023 (15)
C37	0.058 (2)	0.0514 (19)	0.0283 (16)	−0.0082 (16)	0.0049 (15)	−0.0036 (14)
C38	0.047 (2)	0.0372 (15)	0.0279 (15)	−0.0082 (14)	0.0016 (13)	−0.0015 (13)
C39	0.0446 (19)	0.0286 (14)	0.0279 (14)	−0.0032 (13)	0.0023 (13)	0.0000 (12)

Geometric parameters (Å, º) top

Co—O1	2.039 (2)	C12—H12	0.9300
Co—O3	2.269 (2)	C14—C15	1.385 (4)
Co—O4	2.1294 (19)	C14—C19	1.386 (4)
Co—N13	2.085 (2)	C14—H14	0.9300
Co—N23	2.178 (2)	C15—C16	1.395 (5)
Co—N33	2.134 (2)	C15—H15	0.9300
N11—C12	1.327 (4)	C16—C17	1.378 (5)
N11—C18	1.387 (4)	C16—H16	0.9300
N11—H11	0.8600	C17—C18	1.381 (4)
N13—C12	1.323 (4)	C17—H17	0.9300
N13—C19	1.397 (4)	C18—C19	1.410 (4)
N21—C22	1.339 (4)	C22—H22	0.9300
N21—C28	1.369 (4)	C24—C29	1.387 (5)
N21—H21	0.8600	C24—C25	1.390 (5)
N23—C22	1.322 (4)	C24—H24	0.9300
N23—C29	1.409 (4)	C25—C26	1.400 (6)
N31—C32	1.337 (4)	C25—H25	0.9300
N31—C38	1.381 (4)	C26—C27	1.365 (6)
N31—H31	0.8600	C26—H26	0.9300
N33—C32	1.321 (4)	C27—C28	1.395 (5)
N33—C39	1.403 (4)	C27—H27	0.9300
O1—C1	1.263 (4)	C28—C29	1.404 (4)
O2—C1	1.243 (4)	C32—H32	0.9300
O3—C3	1.435 (3)	C34—C35	1.383 (4)
O3—C2	1.440 (3)	C34—C39	1.387 (4)
O4—C4	1.251 (3)	C34—H34	0.9300
O5—C4	1.244 (3)	C35—C36	1.400 (5)
C1—C2	1.508 (4)	C35—H35	0.9300
C2—H2A	0.9700	C36—C37	1.362 (5)
C2—H2B	0.9700	C36—H36	0.9300
C3—C4	1.523 (4)	C37—C38	1.385 (4)
C3—H3A	0.9700	C37—H37	0.9300
C3—H3B	0.9700	C38—C39	1.400 (4)

O1—Co—O3	77.60 (8)	C15—C14—H14	121.6
O1—Co—O4	87.68 (8)	C19—C14—H14	121.6
O1—Co—N13	94.47 (9)	C14—C15—C16	121.7 (3)
O1—Co—N23	93.63 (9)	C14—C15—H15	119.1
O1—Co—N33	165.29 (9)	C16—C15—H15	119.1
O3—Co—O4	76.89 (7)	C17—C16—C15	121.9 (3)
O3—Co—N13	168.69 (8)	C17—C16—H16	119.1
O3—Co—N23	96.61 (8)	C15—C16—H16	119.1
O3—Co—N33	88.88 (8)	C16—C17—C18	116.7 (3)
O4—Co—N13	94.91 (8)	C16—C17—H17	121.6
O4—Co—N23	172.95 (8)	C18—C17—H17	121.6
O4—Co—N33	83.58 (8)	C17—C18—N11	133.1 (3)
N13—Co—N23	91.89 (9)	C17—C18—C19	121.8 (3)
N13—Co—N33	98.03 (9)	N11—C18—C19	104.9 (3)
N33—Co—N23	93.65 (9)	C14—C19—N13	130.2 (3)
C12—N11—C18	107.6 (3)	C14—C19—C18	120.9 (3)
C12—N11—H11	126.2	N13—C19—C18	108.8 (3)
C18—N11—H11	126.2	N23—C22—N21	113.6 (3)
C12—N13—C19	104.8 (2)	N23—C22—H22	123.2
C12—N13—Co	126.5 (2)	N21—C22—H22	123.2
C19—N13—Co	128.63 (19)	C29—C24—C25	116.9 (3)
C22—N21—C28	107.5 (3)	C29—C24—H24	121.6
C22—N21—H21	126.3	C25—C24—H24	121.6
C28—N21—H21	126.3	C24—C25—C26	122.5 (4)
C22—N23—C29	104.4 (2)	C24—C25—H25	118.7
C22—N23—Co	120.2 (2)	C26—C25—H25	118.7
C29—N23—Co	135.09 (19)	C27—C26—C25	120.8 (4)
C32—N31—C38	107.3 (3)	C27—C26—H26	119.6
C32—N31—H31	126.4	C25—C26—H26	119.6
C38—N31—H31	126.4	C26—C27—C28	117.2 (4)
C32—N33—C39	104.7 (2)	C26—C27—H27	121.4
C32—N33—Co	127.1 (2)	C28—C27—H27	121.4
C39—N33—Co	126.08 (19)	N21—C28—C27	131.7 (3)
C1—O1—Co	120.29 (19)	N21—C28—C29	106.0 (3)
C3—O3—C2	114.2 (2)	C27—C28—C29	122.3 (3)
C3—O3—Co	107.62 (16)	C24—C29—C28	120.2 (3)
C2—O3—Co	107.53 (16)	C24—C29—N23	131.4 (3)
C4—O4—Co	116.90 (18)	C28—C29—N23	108.5 (3)
O2—C1—O1	125.8 (3)	N33—C32—N31	113.6 (3)
O2—C1—C2	116.0 (3)	N33—C32—H32	123.2
O1—C1—C2	118.0 (3)	N31—C32—H32	123.2
O3—C2—C1	113.7 (3)	C35—C34—C39	117.7 (3)
O3—C2—H2A	108.8	C35—C34—H34	121.1
C1—C2—H2A	108.8	C39—C34—H34	121.1
O3—C2—H2B	108.8	C34—C35—C36	121.2 (3)
C1—C2—H2B	108.8	C34—C35—H35	119.4
H2A—C2—H2B	107.7	C36—C35—H35	119.4
O3—C3—C4	114.1 (2)	C37—C36—C35	121.5 (3)
O3—C3—H3A	108.7	C37—C36—H36	119.2
C4—C3—H3A	108.7	C35—C36—H36	119.2
O3—C3—H3B	108.7	C36—C37—C38	117.4 (3)
C4—C3—H3B	108.7	C36—C37—H37	121.3
H3A—C3—H3B	107.6	C38—C37—H37	121.3
O5—C4—O4	125.4 (3)	N31—C38—C37	132.4 (3)
O5—C4—C3	115.2 (3)	N31—C38—C39	105.7 (3)
O4—C4—C3	119.4 (2)	C37—C38—C39	122.0 (3)
N13—C12—N11	113.7 (3)	C34—C39—C38	120.1 (3)
N13—C12—H12	123.1	C34—C39—N33	131.1 (3)
N11—C12—H12	123.1	C38—C39—N33	108.8 (3)
C15—C14—C19	116.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O4ⁱ	0.86	2.23	3.039 (3)	157
N11—H11···O5ⁱ	0.86	2.39	3.018 (3)	131
N21—H21···O5ⁱⁱ	0.86	1.96	2.762 (3)	154
N31—H31···O2ⁱⁱⁱ	0.86	1.90	2.756 (3)	178

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₇H₆N₂)₃(C₄H₄O₅)]
M_r	545.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.2152 (4), 10.3120 (2), 19.3617 (4)
β (°)	91.257 (1)
V (Å³)	2438.27 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.26 × 0.09 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.918, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	19382, 4587, 3430
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.114, 1.09
No. of reflections	4587
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.56

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Co—O1	2.039 (2)	Co—N13	2.085 (2)
Co—O3	2.269 (2)	Co—N23	2.178 (2)
Co—O4	2.1294 (19)	Co—N33	2.134 (2)

O1—Co—O3	77.60 (8)	O3—Co—N33	88.88 (8)
O1—Co—O4	87.68 (8)	O4—Co—N13	94.91 (8)
O1—Co—N13	94.47 (9)	O4—Co—N23	172.95 (8)
O1—Co—N23	93.63 (9)	O4—Co—N33	83.58 (8)
O1—Co—N33	165.29 (9)	N13—Co—N23	91.89 (9)
O3—Co—O4	76.89 (7)	N13—Co—N33	98.03 (9)
O3—Co—N13	168.69 (8)	N33—Co—N23	93.65 (9)
O3—Co—N23	96.61 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O4ⁱ	0.86	2.23	3.039 (3)	157
N11—H11···O5ⁱ	0.86	2.39	3.018 (3)	131
N21—H21···O5ⁱⁱ	0.86	1.96	2.762 (3)	154
N31—H31···O2ⁱⁱⁱ	0.86	1.90	2.756 (3)	178

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x, −y+3/2, z+1/2.

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