Tetrakis­(benz­imidazole-κN)(malonato-κ2O,O′)­cobalt(II)

Lin, D.-D.; Liu, Y.; Xu, D.-J.

doi:10.1107/S1600536803018117

Buy article online - an online subscription or single-article purchase is required to access this article.

Tetrakis(benzimidazole-κN)(malonato-κ²O,O′)cobalt(II)

D.-D. Lin, Y. Liu and D.-J. Xu

The title cobalt(II) compound, [Co(C₃H₂O₄)(C₇H₆N₂)₄], displays an octahedral coordination geometry formed by four benzimidazole ligands and one malonate dianion. The malonate chelates to the Co^II atom with both terminal carboxyl groups in a boat configuration. The uncoordinated carboxyl O atoms of the malonate are hydrogen bonded to the neighboring benzimidazole ligands.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018117/fl6052sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018117/fl6052Isup2.hkl Contains datablock I

CCDC reference: 222815

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.045
wR factor = 0.092
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   O1       =       9.92 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   O3       =       9.58 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   N13      =       6.16 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   N23      =       5.29 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   N33      =       7.40 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     -   N43      =       8.82 su
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      59.00 A   3  

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 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
   8 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Aromatic π–π-stacking interactions have been observed in a number of metal complexes with aromatic heteropolycyclic ligands, such as phenathroline, bithiazole and benzimidazole (Chen et al., 2003). As part of our investigation into the π–π-stacking interactions in metal complexes, a new Co^II complex with benzimidazole has recently been prepared. However, its X-ray structure, presented here, shows no π–π stacking occurring in the complex.

The molecular structure of (I) is presented in Fig. 1. Four benzimidazole molecules and one malonate dianion form an octahedral coordination geometry around a Co^II atom. The Co—N13—C19 angle of 133.02 (17)° is much larger than the Co—N13—C12 angle of 122.45 (19)°. Likewise the Co—N33—C39 angle of 134.97 (17)° is much larger than the Co—N33—C32 angle of 120.99 (19)°. The Co—N bonds involving the N13 and N33 atoms are somewhat longer than other two Co—N bonds (Table 1).

The malonate dianion chelates to the Co^II atom with both terminal carboxyl groups in a boat configuration. The uncoordinated carboxyl O atoms of the malonate are hydrogen bonded to the neighboring benzimidazole ligands, as shown in Fig. 2. A three-centered hydrogen bond occurs between benzimidazole atom N31 and the carboxyl groups (see Table 2). The molecular packing diagram is illustrated in Fig. 3. No π–π stacking is observed between benzimidazole rings in the crystal.

Experimental top

An ethanol solution (10 ml) of benzimidazole (0.47 g, 4 mmol) was mixed with an aqueous solution (10 ml)o f CoCl₂·6H₂O (0.24 g, 1 mmol) at room temperature. An aqueous solution (6 ml) containing malonic acid (0.10 g, 1 mmol) and Na₂CO₃ (0.11 g, 1 mmol) was added to the above solution with stirring at room temperature. Then the mixture was refluxed for 1 h and filtered. Blue single crystals were obtained after 3 d.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 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 structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. A diagram showing the hydrogen bonding between uncoordinated carboxyl O atoms and bezimidazole ligands. [Symmetric codes: (v) −1 + x, y, z; (vi) 1 − x, −y, 1 − z; (vii) −0.5 + x, 0.5 − y, 0.5 + z; (viii) 0.5 + x, 0.5 − y, 0.5 + z].
	Fig. 3. The molecular packing diagram.

Tetrakis(benzimidazole-κN)(malonato-κ²O,O')cobalt(II) top

Crystal data top

[Co(C₃H₂O₄)(C₇H₆N₂)₄]	F(000) = 1308
M_r = 633.53	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.2068 (12) Å	Cell parameters from 18608 reflections
b = 25.0492 (16) Å	θ = 2.0–25.0°
c = 13.8555 (13) Å	µ = 0.62 mm⁻¹
β = 109.444 (15)°	T = 295 K
V = 3013.2 (6) Å³	Prism, blue
Z = 4	0.22 × 0.15 × 0.10 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	5357 independent reflections
Radiation source: fine-focus sealed tube	4289 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 10.00 pixels mm^-1	θ_max = 25.2°, θ_min = 1.6°
ω scans	h = −11→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −30→30
T_min = 0.868, T_max = 0.932	l = −14→16
20267 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0381P)² + 1.1717P] where P = (F_o² + 2F_c²)/3
5357 reflections	(Δ/σ)_max = 0.001
397 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Co(C₃H₂O₄)(C₇H₆N₂)₄]	V = 3013.2 (6) Å³
M_r = 633.53	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2068 (12) Å	µ = 0.62 mm⁻¹
b = 25.0492 (16) Å	T = 295 K
c = 13.8555 (13) Å	0.22 × 0.15 × 0.10 mm
β = 109.444 (15)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5357 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4289 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.932	R_int = 0.051
20267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.09	Δρ_max = 0.29 e Å⁻³
5357 reflections	Δρ_min = −0.29 e Å⁻³
397 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	0.43452 (3)	0.145631 (13)	0.41332 (2)	0.02684 (10)
O1	0.33190 (19)	0.10648 (7)	0.50578 (13)	0.0372 (4)
O2	0.1777 (2)	0.09822 (8)	0.59632 (16)	0.0515 (5)
O3	0.37999 (19)	0.21523 (7)	0.47396 (13)	0.0378 (4)
O4	0.2632 (2)	0.26317 (7)	0.56000 (14)	0.0432 (5)
N11	0.8971 (2)	0.12291 (10)	0.60727 (18)	0.0476 (6)
H11	0.9894	0.1140	0.6121	0.057*
N13	0.6481 (2)	0.14071 (9)	0.53555 (16)	0.0376 (5)
N21	0.6475 (3)	0.22281 (10)	0.21847 (17)	0.0483 (6)
H21	0.6642	0.2250	0.1611	0.058*
N23	0.5536 (2)	0.19254 (9)	0.33624 (15)	0.0358 (5)
N31	0.5808 (3)	−0.01106 (10)	0.3742 (2)	0.0653 (8)
H31	0.6295	−0.0391	0.4038	0.078*
N33	0.4830 (2)	0.07062 (8)	0.35698 (16)	0.0377 (5)
N41	0.0224 (3)	0.18216 (10)	0.17191 (18)	0.0500 (6)
H41	−0.0315	0.2046	0.1273	0.060*
N43	0.2224 (2)	0.14783 (9)	0.29398 (16)	0.0385 (5)
C1	0.2260 (3)	0.12385 (10)	0.53656 (19)	0.0334 (6)
C2	0.1554 (3)	0.17827 (10)	0.5000 (2)	0.0364 (6)
H2A	0.0919	0.1756	0.4286	0.044*
H2B	0.0890	0.1882	0.5387	0.044*
C3	0.2747 (3)	0.22196 (10)	0.51143 (18)	0.0314 (6)
C12	0.7767 (3)	0.12673 (11)	0.5212 (2)	0.0410 (6)
H12	0.7833	0.1201	0.4568	0.049*
C14	0.6039 (3)	0.16449 (12)	0.7018 (2)	0.0438 (7)
H14	0.4996	0.1723	0.6730	0.053*
C15	0.6787 (4)	0.16920 (14)	0.8055 (2)	0.0547 (8)
H15	0.6239	0.1808	0.8471	0.066*
C16	0.8334 (4)	0.15712 (16)	0.8495 (2)	0.0673 (10)
H16	0.8800	0.1607	0.9199	0.081*
C17	0.9195 (4)	0.14003 (15)	0.7915 (2)	0.0640 (9)
H17	1.0233	0.1315	0.8211	0.077*
C18	0.8454 (3)	0.13607 (11)	0.6872 (2)	0.0426 (7)
C19	0.6891 (3)	0.14767 (11)	0.64135 (19)	0.0356 (6)
C22	0.5631 (3)	0.18557 (11)	0.2449 (2)	0.0408 (6)
H22	0.5157	0.1574	0.2023	0.049*
C24	0.6794 (3)	0.26330 (12)	0.4683 (2)	0.0458 (7)
H24	0.6415	0.2512	0.5188	0.055*
C25	0.7733 (4)	0.30748 (13)	0.4837 (2)	0.0592 (9)
H25	0.7990	0.3254	0.5460	0.071*
C26	0.8308 (4)	0.32622 (15)	0.4090 (3)	0.0660 (10)
H26	0.8947	0.3560	0.4228	0.079*
C27	0.7956 (4)	0.30180 (14)	0.3159 (3)	0.0603 (9)
H27	0.8322	0.3146	0.2653	0.072*
C28	0.7020 (3)	0.25676 (12)	0.3006 (2)	0.0421 (7)
C29	0.6433 (3)	0.23761 (11)	0.37456 (19)	0.0360 (6)
C32	0.5630 (3)	0.03383 (11)	0.4197 (2)	0.0489 (7)
H32	0.6037	0.0388	0.4901	0.059*
C34	0.3557 (4)	0.06445 (13)	0.1634 (2)	0.0539 (8)
H34	0.3105	0.0981	0.1540	0.065*
C35	0.3374 (5)	0.03078 (15)	0.0822 (3)	0.0774 (11)
H35	0.2781	0.0418	0.0169	0.093*
C36	0.4058 (6)	−0.01994 (16)	0.0953 (3)	0.0916 (14)
H36	0.3933	−0.0414	0.0383	0.110*
C37	0.4901 (5)	−0.03839 (15)	0.1896 (3)	0.0814 (12)
H37	0.5341	−0.0722	0.1986	0.098*
C38	0.5074 (4)	−0.00444 (11)	0.2717 (2)	0.0532 (8)
C39	0.4440 (3)	0.04673 (11)	0.2604 (2)	0.0413 (6)
C42	0.1678 (3)	0.18911 (11)	0.2344 (2)	0.0406 (6)
H42	0.2243	0.2200	0.2354	0.049*
C44	0.0902 (4)	0.06027 (13)	0.3074 (3)	0.0604 (9)
H47	0.1737	0.0448	0.3572	0.072*
C45	−0.0487 (4)	0.03403 (15)	0.2691 (3)	0.0791 (11)
H46	−0.0600	0.0006	0.2947	0.095*
C46	−0.1734 (4)	0.05690 (18)	0.1920 (3)	0.0827 (12)
H45	−0.2654	0.0380	0.1675	0.099*
C47	−0.1639 (4)	0.10582 (16)	0.1521 (3)	0.0677 (10)
H44	−0.2465	0.1206	0.1005	0.081*
C48	−0.0247 (3)	0.13259 (12)	0.1923 (2)	0.0463 (7)
C49	0.1008 (3)	0.11084 (11)	0.2688 (2)	0.0429 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co	0.02617 (17)	0.02967 (18)	0.02670 (17)	0.00307 (15)	0.01149 (13)	0.00153 (15)
O1	0.0352 (10)	0.0380 (10)	0.0429 (10)	0.0089 (8)	0.0192 (8)	0.0044 (8)
O2	0.0465 (11)	0.0525 (13)	0.0680 (14)	0.0117 (9)	0.0357 (10)	0.0239 (11)
O3	0.0344 (9)	0.0391 (10)	0.0454 (11)	−0.0018 (8)	0.0205 (8)	−0.0019 (8)
O4	0.0467 (11)	0.0441 (11)	0.0445 (11)	−0.0051 (9)	0.0229 (9)	−0.0138 (9)
N11	0.0289 (12)	0.0657 (17)	0.0490 (14)	0.0058 (11)	0.0141 (11)	0.0035 (12)
N13	0.0315 (11)	0.0485 (14)	0.0356 (12)	0.0052 (10)	0.0150 (9)	0.0019 (10)
N21	0.0570 (15)	0.0619 (16)	0.0350 (13)	−0.0100 (12)	0.0274 (11)	−0.0006 (12)
N23	0.0375 (12)	0.0415 (13)	0.0307 (11)	−0.0016 (10)	0.0146 (10)	−0.0006 (9)
N31	0.087 (2)	0.0335 (15)	0.0652 (18)	0.0167 (14)	0.0125 (16)	0.0073 (13)
N33	0.0429 (12)	0.0357 (12)	0.0359 (12)	0.0051 (10)	0.0149 (10)	0.0047 (10)
N41	0.0452 (14)	0.0491 (15)	0.0466 (14)	0.0097 (12)	0.0031 (12)	0.0070 (12)
N43	0.0403 (12)	0.0355 (12)	0.0390 (12)	0.0022 (11)	0.0119 (10)	0.0021 (11)
C1	0.0285 (13)	0.0364 (14)	0.0357 (14)	0.0022 (11)	0.0114 (11)	0.0012 (12)
C2	0.0280 (13)	0.0373 (15)	0.0473 (15)	0.0033 (11)	0.0172 (12)	0.0014 (12)
C3	0.0306 (13)	0.0329 (14)	0.0284 (13)	0.0035 (11)	0.0068 (11)	0.0036 (11)
C12	0.0351 (15)	0.0503 (17)	0.0401 (15)	0.0019 (12)	0.0158 (12)	0.0006 (13)
C14	0.0374 (15)	0.0579 (18)	0.0393 (15)	0.0022 (13)	0.0168 (12)	−0.0032 (13)
C15	0.0528 (18)	0.075 (2)	0.0403 (16)	−0.0084 (16)	0.0213 (14)	−0.0086 (16)
C16	0.055 (2)	0.105 (3)	0.0366 (17)	−0.0173 (19)	0.0086 (15)	−0.0037 (17)
C17	0.0374 (16)	0.100 (3)	0.0466 (18)	−0.0023 (18)	0.0033 (14)	0.0038 (19)
C18	0.0306 (14)	0.0523 (18)	0.0440 (16)	−0.0020 (12)	0.0114 (12)	0.0050 (13)
C19	0.0320 (13)	0.0387 (14)	0.0346 (13)	−0.0040 (12)	0.0092 (11)	0.0019 (12)
C22	0.0463 (16)	0.0454 (17)	0.0340 (15)	−0.0037 (13)	0.0179 (13)	−0.0020 (12)
C24	0.0482 (17)	0.0571 (19)	0.0347 (15)	−0.0092 (14)	0.0173 (13)	−0.0035 (13)
C25	0.0586 (19)	0.070 (2)	0.0481 (18)	−0.0238 (17)	0.0160 (16)	−0.0149 (16)
C26	0.062 (2)	0.070 (2)	0.069 (2)	−0.0328 (18)	0.0260 (18)	−0.0122 (19)
C27	0.060 (2)	0.070 (2)	0.059 (2)	−0.0267 (17)	0.0308 (16)	0.0000 (17)
C28	0.0382 (15)	0.0541 (18)	0.0379 (15)	−0.0040 (13)	0.0179 (12)	0.0017 (13)
C29	0.0323 (13)	0.0420 (15)	0.0354 (14)	−0.0045 (12)	0.0136 (11)	0.0000 (12)
C32	0.0608 (19)	0.0380 (17)	0.0449 (17)	0.0027 (14)	0.0135 (15)	0.0061 (14)
C34	0.074 (2)	0.0447 (17)	0.0405 (16)	−0.0017 (16)	0.0152 (15)	−0.0006 (14)
C35	0.118 (3)	0.065 (2)	0.0445 (19)	−0.012 (2)	0.021 (2)	−0.0072 (17)
C36	0.150 (4)	0.059 (3)	0.065 (3)	−0.010 (3)	0.035 (3)	−0.029 (2)
C37	0.121 (3)	0.045 (2)	0.080 (3)	0.004 (2)	0.035 (3)	−0.0166 (19)
C38	0.072 (2)	0.0332 (16)	0.0586 (19)	0.0012 (15)	0.0274 (17)	−0.0017 (14)
C39	0.0503 (17)	0.0335 (15)	0.0437 (16)	−0.0001 (13)	0.0204 (13)	−0.0012 (12)
C42	0.0398 (15)	0.0409 (16)	0.0409 (15)	0.0039 (13)	0.0133 (13)	0.0009 (13)
C44	0.059 (2)	0.0462 (19)	0.066 (2)	−0.0118 (16)	0.0063 (16)	0.0037 (16)
C45	0.081 (3)	0.062 (2)	0.084 (3)	−0.028 (2)	0.014 (2)	0.002 (2)
C46	0.061 (2)	0.091 (3)	0.084 (3)	−0.031 (2)	0.007 (2)	−0.011 (2)
C47	0.0457 (19)	0.077 (3)	0.067 (2)	−0.0058 (18)	0.0007 (16)	−0.0081 (19)
C48	0.0398 (16)	0.0510 (19)	0.0434 (16)	0.0039 (13)	0.0076 (13)	−0.0036 (13)
C49	0.0424 (16)	0.0427 (17)	0.0411 (15)	−0.0022 (13)	0.0106 (13)	−0.0027 (13)

Geometric parameters (Å, º) top

Co—O3	2.0684 (18)	C15—H15	0.93
Co—O1	2.0741 (17)	C16—C17	1.371 (5)
Co—N43	2.098 (2)	C16—H16	0.93
Co—N23	2.122 (2)	C17—C18	1.381 (4)
Co—N13	2.129 (2)	C17—H17	0.93
Co—N33	2.138 (2)	C18—C19	1.397 (3)
O1—C1	1.264 (3)	C22—H22	0.93
O2—C1	1.242 (3)	C24—C25	1.376 (4)
O3—C3	1.254 (3)	C24—C29	1.387 (4)
O4—C3	1.256 (3)	C24—H24	0.93
N11—C12	1.334 (3)	C25—C26	1.392 (4)
N11—C18	1.383 (4)	C25—H25	0.93
N11—H11	0.86	C26—C27	1.366 (4)
N13—C12	1.311 (3)	C26—H26	0.93
N13—C19	1.398 (3)	C27—C28	1.392 (4)
N21—C22	1.341 (3)	C27—H27	0.93
N21—C28	1.375 (3)	C28—C29	1.393 (4)
N21—H21	0.86	C32—H32	0.93
N23—C22	1.309 (3)	C34—C35	1.371 (4)
N23—C29	1.396 (3)	C34—C39	1.391 (4)
N31—C32	1.325 (4)	C34—H34	0.93
N31—C38	1.365 (4)	C35—C36	1.403 (5)
N31—H31	0.86	C35—H35	0.93
N33—C32	1.312 (3)	C36—C37	1.359 (5)
N33—C39	1.399 (3)	C36—H36	0.93
N41—C42	1.342 (3)	C37—C38	1.386 (4)
N41—C48	1.375 (4)	C37—H37	0.93
N41—H41	0.86	C38—C39	1.396 (4)
N43—C42	1.314 (3)	C42—H42	0.93
N43—C49	1.405 (3)	C44—C45	1.377 (4)
C1—C2	1.523 (3)	C44—C49	1.391 (4)
C2—C3	1.521 (3)	C44—H47	0.93
C2—H2A	0.97	C45—C46	1.404 (5)
C2—H2B	0.97	C45—H46	0.93
C12—H12	0.93	C46—C47	1.359 (5)
C14—C15	1.376 (4)	C46—H45	0.93
C14—C19	1.390 (4)	C47—C48	1.389 (4)
C14—H14	0.93	C47—H44	0.93
C15—C16	1.383 (4)	C48—C49	1.392 (4)

O3—Co—O1	85.73 (7)	C17—C18—C19	122.5 (3)
O3—Co—N43	90.56 (8)	N11—C18—C19	105.2 (2)
O1—Co—N43	90.19 (8)	C14—C19—N13	131.3 (2)
O3—Co—N23	88.49 (8)	C14—C19—C18	119.5 (2)
O1—Co—N23	172.16 (8)	N13—C19—C18	109.2 (2)
N43—Co—N23	95.17 (8)	N23—C22—N21	113.7 (2)
O3—Co—N13	90.60 (8)	N23—C22—H22	123.1
O1—Co—N13	88.36 (7)	N21—C22—H22	123.1
N43—Co—N13	178.07 (9)	C25—C24—C29	117.4 (3)
N23—Co—N13	86.40 (8)	C25—C24—H24	121.3
O3—Co—N33	175.92 (8)	C29—C24—H24	121.3
O1—Co—N33	90.19 (7)	C24—C25—C26	122.1 (3)
N43—Co—N33	89.32 (8)	C24—C25—H25	119.0
N23—Co—N33	95.59 (8)	C26—C25—H25	119.0
N13—Co—N33	89.41 (8)	C27—C26—C25	121.5 (3)
C1—O1—Co	127.34 (17)	C27—C26—H26	119.3
C3—O3—Co	127.39 (17)	C25—C26—H26	119.3
C12—N11—C18	107.1 (2)	C26—C27—C28	116.5 (3)
C12—N11—H11	126.5	C26—C27—H27	121.7
C18—N11—H11	126.5	C28—C27—H27	121.7
C12—N13—C19	104.5 (2)	N21—C28—C29	105.8 (2)
C12—N13—Co	122.45 (19)	N21—C28—C27	131.6 (3)
C19—N13—Co	133.02 (17)	C29—C28—C27	122.6 (3)
C22—N21—C28	106.8 (2)	C24—C29—C28	119.9 (2)
C22—N21—H21	126.6	C24—C29—N23	131.2 (2)
C28—N21—H21	126.6	C28—C29—N23	108.9 (2)
C22—N23—C29	104.7 (2)	N33—C32—N31	114.3 (3)
C22—N23—Co	128.66 (19)	N33—C32—H32	122.8
C29—N23—Co	126.61 (16)	N31—C32—H32	122.8
C32—N31—C38	107.2 (2)	C35—C34—C39	118.0 (3)
C32—N31—H31	126.4	C35—C34—H34	121.0
C38—N31—H31	126.4	C39—C34—H34	121.0
C32—N33—C39	104.0 (2)	C34—C35—C36	121.6 (3)
C32—N33—Co	120.99 (19)	C34—C35—H35	119.2
C39—N33—Co	134.97 (17)	C36—C35—H35	119.2
C42—N41—C48	107.4 (2)	C37—C36—C35	121.4 (3)
C42—N41—H41	126.3	C37—C36—H36	119.3
C48—N41—H41	126.3	C35—C36—H36	119.3
C42—N43—C49	104.8 (2)	C36—C37—C38	116.9 (3)
C42—N43—Co	125.23 (18)	C36—C37—H37	121.5
C49—N43—Co	129.37 (18)	C38—C37—H37	121.5
O2—C1—O1	122.3 (2)	N31—C38—C37	131.4 (3)
O2—C1—C2	118.4 (2)	N31—C38—C39	105.8 (3)
O1—C1—C2	119.2 (2)	C37—C38—C39	122.8 (3)
C3—C2—C1	113.3 (2)	C34—C39—C38	119.3 (3)
C3—C2—H2A	108.9	C34—C39—N33	132.0 (3)
C1—C2—H2A	108.9	C38—C39—N33	108.7 (2)
C3—C2—H2B	108.9	N43—C42—N41	113.2 (3)
C1—C2—H2B	108.9	N43—C42—H42	123.4
H2A—C2—H2B	107.7	N41—C42—H42	123.4
O3—C3—O4	123.2 (2)	C45—C44—C49	117.5 (3)
O3—C3—C2	119.4 (2)	C45—C44—H47	121.3
O4—C3—C2	117.4 (2)	C49—C44—H47	121.3
N13—C12—N11	114.1 (3)	C44—C45—C46	121.2 (4)
N13—C12—H12	123.0	C44—C45—H46	119.4
N11—C12—H12	123.0	C46—C45—H46	119.4
C15—C14—C19	117.9 (3)	C47—C46—C45	122.0 (3)
C15—C14—H14	121.0	C47—C46—H45	119.0
C19—C14—H14	121.0	C45—C46—H45	119.0
C14—C15—C16	121.7 (3)	C46—C47—C48	116.6 (3)
C14—C15—H15	119.2	C46—C47—H44	121.7
C16—C15—H15	119.2	C48—C47—H44	121.7
C17—C16—C15	121.4 (3)	N41—C48—C47	131.7 (3)
C17—C16—H16	119.3	N41—C48—C49	105.7 (2)
C15—C16—H16	119.3	C47—C48—C49	122.5 (3)
C16—C17—C18	117.0 (3)	C44—C49—C48	120.1 (3)
C16—C17—H17	121.5	C44—C49—N43	131.1 (3)
C18—C17—H17	121.5	C48—C49—N43	108.8 (2)
C17—C18—N11	132.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O2ⁱ	0.86	1.86	2.709 (3)	169
N21—H21···O4ⁱⁱ	0.86	1.93	2.764 (3)	162
N31—H31···O1ⁱⁱⁱ	0.86	2.06	2.870 (3)	156
N31—H31···O2ⁱⁱⁱ	0.86	2.31	3.045 (3)	143
N41—H41···O4^iv	0.86	1.98	2.741 (3)	147

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

Experimental details

Crystal data
Chemical formula	[Co(C₃H₂O₄)(C₇H₆N₂)₄]
M_r	633.53
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.2068 (12), 25.0492 (16), 13.8555 (13)
β (°)	109.444 (15)
V (Å³)	3013.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.22 × 0.15 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.868, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	20267, 5357, 4289
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.092, 1.09
No. of reflections	5357
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.29

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC and Rigaku, 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—O3	2.0684 (18)	Co—N23	2.122 (2)
Co—O1	2.0741 (17)	Co—N13	2.129 (2)
Co—N43	2.098 (2)	Co—N33	2.138 (2)

C12—N13—Co	122.45 (19)	C32—N33—Co	120.99 (19)
C19—N13—Co	133.02 (17)	C39—N33—Co	134.97 (17)
C22—N23—Co	128.66 (19)	C42—N43—Co	125.23 (18)
C29—N23—Co	126.61 (16)	C49—N43—Co	129.37 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O2ⁱ	0.86	1.86	2.709 (3)	169
N21—H21···O4ⁱⁱ	0.86	1.93	2.764 (3)	162
N31—H31···O1ⁱⁱⁱ	0.86	2.06	2.870 (3)	156
N31—H31···O2ⁱⁱⁱ	0.86	2.31	3.045 (3)	143
N41—H41···O4^iv	0.86	1.98	2.741 (3)	147

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page