Hydroxonium creatininium bis­(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)cobaltate(II) trihydrate

Aghabozorg, H.; Derikvand, Z.; Attar Gharamaleki, J.; Yousefi, M.

doi:10.1107/S1600536809021837

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m826-m827

doi:10.1107/S1600536809021837

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Hydroxonium creatininium bis(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)cobaltate(II) trihydrate

Hossein Aghabozorg,^a ^* Zohreh Derikvand,^b Jafar Attar Gharamaleki ^c and Mohammad Yousefi ^d

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, Faculty of Science, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, ^cYoung Researchers Club, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^dDepartment of Chemistry, Islamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 19 May 2009; accepted 9 June 2009; online 27 June 2009)

The title compound, (C₄H₈N₃O)(H₃O)[Co(C₇H₃NO₄)₂]·3H₂O, contains a protonated creatininium cation, a hydroxonium (H₃O)⁺ cation, a [Co(pydc)₂]²⁻ (pydcH₂ = pyridine-2,6-dicarboxylic acid) complex anion, and three uncoordinated water molecules. The Co^II atom is coordinated by four O and two N atoms from two pydc ligands in a distorted octahedral environment. The structure also contains three uncoordinated water molecules. Extensive intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, π–π stacking interactions [centroid–centroid distances = 3.565 (14) and 3.425 (14) Å] and O⋯π interactions [O⋯centroid distance = 3.480 (2) Å] connect the various components in the crystal structure.

Related literature

For related structures, see: Aghabozorg, Derikvand et al. (2008 ); Aghabozorg, Ramezanipour et al. (2008 ); Moghimi et al. (2004 , 2005 ). For a review article on proton-transfer agents and their metal complexes, see: Aghabozorg, Manteghi et al. (2008 ). For the isotypic Ni compound, see: Attar Gharamaleki et al. (2009 ).

Experimental

Crystal data

(C₄H₈N₃O)(H₃O)[Co(C₇H₃NO₄)₂]·3H₂O
M_r = 576.34
Triclinic, $[P \overline 1]$
a = 8.0937 (10) Å
b = 10.7389 (13) Å
c = 13.5976 (17) Å
α = 104.811 (2)°
β = 90.267 (2)°
γ = 92.415 (1)°
V = 1141.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 120 K
0.18 × 0.12 × 0.09 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.889, T_max = 0.930
11652 measured reflections
5488 independent reflections
4149 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.097
S = 1.02
5488 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.77 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.029 (2)
Co1—N2	2.031 (2)
Co1—O8	2.1273 (18)
Co1—O4	2.1389 (18)
Co1—O5	2.1904 (18)
Co1—O1	2.2239 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1Wⁱ	0.88	1.86	2.716 (3)	164
N5—H5A⋯O5	0.88	2.15	2.882 (3)	141
N5—H5B⋯O3ⁱⁱ	0.88	1.96	2.764 (3)	152
O1W—H1⋯O4ⁱⁱⁱ	0.85	1.95	2.782 (3)	166
O1W—H2⋯O3W^iv	0.85	1.85	2.673 (3)	164
O2W—H3⋯O4W^v	0.85	1.70	2.522 (3)	163
O2W—H4⋯O6^vi	0.85	1.64	2.481 (3)	170
O2W—H5⋯O2	0.85	1.71	2.537 (3)	164
O3W—H6⋯O7ⁱⁱⁱ	0.85	1.93	2.778 (3)	172
O3W—H7⋯O9^vii	0.85	2.22	2.948 (3)	144
O4W—H8⋯O7^viii	0.85	1.84	2.680 (3)	169
O4W—H9⋯O1	0.85	1.87	2.718 (3)	172
C3—H3B⋯O9^vii	0.95	2.37	3.301 (3)	165
C4—H4A⋯O8^ix	0.95	2.43	3.252 (3)	145
C18—H18C⋯O7ⁱⁱⁱ	0.98	2.60	3.535 (4)	160
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1; (iii) x, y-1, z; (iv) x-1, y, z; (v) -x+1, -y+1, -z; (vi) x+1, y, z; (vii) -x+1, -y+1, -z+1; (viii) -x+1, -y+2, -z; (ix) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021837/hy2201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021837/hy2201Isup2.hkl

checkCIF report

Comment top

We have previously reported some compounds containing creatinine (creat), pyridine-2,6-dicarboxylic acid (pydcH₂) and various metals, such as (creatH)(pydcH).H₂O (Moghimi et al., 2004), (creatH)₂[Bi(pydc)₂]₂.4H₂O (Moghimi et al., 2005), (creatH)[Zn(pydc)(pydcH)].4H₂O (Aghabozorg, Ramezanipour et al., 2008) and (creatH)[Cr(pydc)₂](pydcH₂).6H₂O (Aghabozorg, Derikvand et al., 2008). For more details and related literature see our recent review article (Aghabozorg, Manteghi et al., 2008).

We describe here the crystal structure of the title compound. The compound contains a [Co(pydc)₂]^2- anion, a (creatH)⁺ and a (H₃O)⁺ cation, and three uncoordinated water molecules (Fig. 1). In the anion, the Co^II atom is six-coordinated by two N atoms (N1 and N2) and four O atoms (O1, O4, O5 and O8) from the carboxylate groups of two (pydc)^2- ligands, with the bond length range of 2.029 (2)–2.2239 (19) Å (Table 1). The N1—Co1—N2 [171.90 (8)°], O8—Co1—O5 [151.26 (7)°] and O4—Co1—O1 [152.09 (7)°] angles show that the four carboxylate groups of the two (pydc)^2- ligands orient in a flattened tetrahedral arrangement around the central atom. The coordination environment around Co^II is distorted octahedral. The O8—Co1—O4—C7 and O1—Co1—O8—C14 torsion angles are -95.15 (17)° and 95.48 (19)°, respectively, thus it can be concluded that two (pydc)^2- ligands are almost perpendicular to each other. The intermolecular forces in the structure could be divided in three main branches, ionic interactions which gather principal anionic complex and counter cation together, X—H···O hydrogen bonds (Fig. 2 and Table 2), where X= O, N, C, and O···π, π–π stacking interactions. The π–π stacking interactions between the pyridyl rings, with centroid–centroid distances of 3.565 (14) and 3.425 (14) Å, and the O···π interaction between the carboxylate O atom and pyridyl ring, with an O···centroid distance of 3.480 (2)Å are observed (Fig. 3). Ion pairing, π–π stacking interactions and extensive intermolecular hydrogen bonds connected the various components into a supramolecular structure.

Related literature top

For related structures, see: Aghabozorg, Derikvand et al. (2008); Aghabozorg, Ramezanipour et al. (2008); Moghimi et al. (2004, 2005). For a review article, see: Aghabozorg, Manteghi et al. (2008). For the isotypic Ni compound, see: Attar Gharamaleki et al. (2009).

Experimental top

The reaction between pyridine-2,6-dicarboxylic acid (100 mg, 1 mmol) in 10 ml water, cratinine (110 mg, 1 mmol) in 20 ml water and Co(NO₃)₂.6H₂O (87 mg, 0.5 mmol) in 5 ml water at a 2:2:1 molar ratio gave a red compound after slow evaporation of the solvent at the room temperature. The crystals obtained were stable in air.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram of the title compound. Hydrogen bonds are shown by dashed lines.
	Fig. 3. The π–π and O···π stacking interactions in the title compound. The centroid–centroid distances are 3.425 (14) Å between Cg1 (N1, C2–C6) and Cg1ⁱ, and 3.565 (14) Å between Cg2ⁱⁱ (N2ⁱⁱ, C9ⁱⁱ–C13ⁱⁱ) and Cg2ⁱⁱⁱ. The O7···Cg2ⁱⁱⁱ distance is 3.480 (2) Å. [Symmetry codes: (i) 1-x, 2-y, 1-z; (ii) 1+x, y, z; (iii) 1-x, 2-y, -z.]

Hydroxonium creatininium bis(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)cobaltate(II) trihydrate top

Crystal data top

(C₄H₈N₃O)(H₃O)[Co(C₇H₃NO₄)₂]·3H₂O	Z = 2
M_r = 576.34	F(000) = 594
Triclinic, P1	D_x = 1.677 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0937 (10) Å	Cell parameters from 843 reflections
b = 10.7389 (13) Å	θ = 3–27°
c = 13.5976 (17) Å	µ = 0.83 mm⁻¹
α = 104.811 (2)°	T = 120 K
β = 90.267 (2)°	Prism, red
γ = 92.415 (1)°	0.18 × 0.12 × 0.09 mm
V = 1141.4 (2) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	5488 independent reflections
Radiation source: fine-focus sealed tube	4149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 28.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.889, T_max = 0.930	k = −14→14
11652 measured reflections	l = −17→17

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: mixed
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.015P)² + 2.6P] where P = (F_o² + 2F_c²)/3
5488 reflections	(Δ/σ)_max < 0.001
335 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

(C₄H₈N₃O)(H₃O)[Co(C₇H₃NO₄)₂]·3H₂O	γ = 92.415 (1)°
M_r = 576.34	V = 1141.4 (2) Å³
Triclinic, P1	Z = 2
a = 8.0937 (10) Å	Mo Kα radiation
b = 10.7389 (13) Å	µ = 0.83 mm⁻¹
c = 13.5976 (17) Å	T = 120 K
α = 104.811 (2)°	0.18 × 0.12 × 0.09 mm
β = 90.267 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5488 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4149 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.930	R_int = 0.025
11652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.02	Δρ_max = 0.77 e Å⁻³
5488 reflections	Δρ_min = −0.45 e Å⁻³
335 parameters

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

	x	y	z	U_iso*/U_eq
Co1	0.26506 (4)	0.93000 (3)	0.23131 (3)	0.01942 (10)
O1	0.4562 (2)	0.78341 (18)	0.19033 (13)	0.0230 (4)
O2	0.6104 (2)	0.65616 (18)	0.25814 (14)	0.0252 (4)
O3	0.0940 (2)	1.13617 (18)	0.50661 (14)	0.0254 (4)
O4	0.1083 (2)	1.04931 (18)	0.33852 (13)	0.0232 (4)
O5	0.0722 (2)	0.78287 (17)	0.16490 (13)	0.0220 (4)
O6	−0.0601 (2)	0.69039 (18)	0.01715 (13)	0.0249 (4)
O7	0.4810 (2)	1.23340 (18)	0.13445 (13)	0.0238 (4)
O8	0.4131 (2)	1.09779 (18)	0.22942 (13)	0.0241 (4)
O9	0.2979 (2)	0.47606 (19)	0.53766 (14)	0.0287 (4)
N1	0.3283 (2)	0.89101 (19)	0.36453 (15)	0.0161 (4)
N2	0.2268 (2)	0.9517 (2)	0.08903 (15)	0.0170 (4)
N3	0.1336 (3)	0.5901 (2)	0.45644 (15)	0.0181 (4)
H3A	0.0801	0.6346	0.5091	0.022*
N4	0.2130 (3)	0.5206 (2)	0.29648 (16)	0.0202 (4)
N5	0.0027 (3)	0.6690 (2)	0.33142 (15)	0.0210 (5)
H5A	−0.0074	0.6703	0.2672	0.025*
H5B	−0.0602	0.7165	0.3776	0.025*
C1	0.5092 (3)	0.7418 (2)	0.26371 (18)	0.0188 (5)
C2	0.4403 (3)	0.8035 (2)	0.36658 (19)	0.0180 (5)
C3	0.4860 (3)	0.7762 (2)	0.45730 (19)	0.0198 (5)
H3B	0.5660	0.7143	0.4584	0.024*
C4	0.4112 (3)	0.8422 (2)	0.54679 (19)	0.0203 (5)
H4A	0.4382	0.8245	0.6098	0.024*
C5	0.2971 (3)	0.9341 (2)	0.54291 (19)	0.0206 (5)
H5C	0.2460	0.9807	0.6031	0.025*
C6	0.2589 (3)	0.9566 (2)	0.44902 (18)	0.0174 (5)
C7	0.1427 (3)	1.0555 (2)	0.43192 (19)	0.0190 (5)
C8	0.0403 (3)	0.7707 (2)	0.07148 (18)	0.0191 (5)
C9	0.1295 (3)	0.8660 (2)	0.02324 (18)	0.0177 (5)
C10	0.1127 (3)	0.8709 (3)	−0.07723 (19)	0.0201 (5)
H10A	0.0447	0.8087	−0.1240	0.024*
C11	0.1983 (3)	0.9690 (3)	−0.10736 (19)	0.0222 (5)
H11A	0.1896	0.9743	−0.1759	0.027*
C12	0.2966 (3)	1.0597 (3)	−0.03808 (19)	0.0200 (5)
H12A	0.3538	1.1283	−0.0578	0.024*
C13	0.3090 (3)	1.0472 (2)	0.06107 (19)	0.0180 (5)
C14	0.4103 (3)	1.1339 (2)	0.14799 (19)	0.0199 (5)
C15	0.1105 (3)	0.5968 (2)	0.35806 (18)	0.0182 (5)
C16	0.3147 (3)	0.4547 (3)	0.35453 (19)	0.0221 (5)
H16A	0.4336	0.4783	0.3505	0.027*
H16B	0.2976	0.3599	0.3303	0.027*
C17	0.2520 (3)	0.5040 (3)	0.4611 (2)	0.0213 (5)
C18	0.2037 (4)	0.4869 (3)	0.18563 (19)	0.0279 (6)
H18A	0.2195	0.5652	0.1617	0.042*
H18B	0.0951	0.4457	0.1627	0.042*
H18C	0.2903	0.4272	0.1580	0.042*
O1W	−0.0036 (2)	0.29618 (18)	0.36045 (14)	0.0249 (4)
H1	0.0162	0.2166	0.3476	0.037*
H2	−0.0856	0.3008	0.3225	0.037*
O2W	0.7786 (2)	0.55028 (19)	0.10484 (14)	0.0293 (4)
H3	0.7269	0.4912	0.0603	0.044*
H4	0.8232	0.6010	0.0728	0.044*
H5	0.7115	0.5907	0.1481	0.044*
O3W	0.7461 (3)	0.3583 (2)	0.25576 (16)	0.0362 (5)
H6	0.6588	0.3236	0.2235	0.054*
H7	0.7240	0.4284	0.2983	0.054*
O4W	0.3941 (3)	0.6406 (2)	−0.00313 (15)	0.0468 (7)
H8	0.4336	0.6891	−0.0386	0.070*
H9	0.4122	0.6782	0.0592	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02341 (19)	0.02192 (19)	0.01396 (17)	0.00133 (14)	−0.00051 (13)	0.00646 (13)
O1	0.0280 (10)	0.0275 (10)	0.0147 (9)	0.0058 (8)	0.0015 (7)	0.0067 (7)
O2	0.0268 (10)	0.0296 (10)	0.0195 (9)	0.0106 (8)	0.0029 (8)	0.0051 (8)
O3	0.0299 (10)	0.0242 (10)	0.0208 (9)	0.0052 (8)	0.0040 (8)	0.0027 (8)
O4	0.0289 (10)	0.0246 (10)	0.0173 (9)	0.0063 (8)	0.0022 (7)	0.0065 (7)
O5	0.0269 (10)	0.0249 (10)	0.0152 (9)	−0.0037 (8)	−0.0011 (7)	0.0075 (7)
O6	0.0303 (10)	0.0264 (10)	0.0168 (9)	−0.0080 (8)	−0.0021 (8)	0.0048 (8)
O7	0.0279 (10)	0.0247 (10)	0.0197 (9)	−0.0077 (8)	−0.0030 (8)	0.0091 (8)
O8	0.0328 (10)	0.0253 (10)	0.0155 (9)	−0.0052 (8)	−0.0017 (8)	0.0086 (7)
O9	0.0327 (11)	0.0354 (11)	0.0201 (9)	0.0093 (9)	−0.0025 (8)	0.0100 (8)
N1	0.0173 (10)	0.0173 (10)	0.0136 (9)	−0.0022 (8)	0.0000 (8)	0.0042 (8)
N2	0.0173 (10)	0.0195 (11)	0.0142 (10)	0.0018 (8)	−0.0002 (8)	0.0043 (8)
N3	0.0199 (10)	0.0216 (11)	0.0133 (10)	0.0024 (8)	0.0011 (8)	0.0050 (8)
N4	0.0224 (11)	0.0230 (11)	0.0153 (10)	0.0054 (9)	−0.0002 (8)	0.0047 (9)
N5	0.0255 (11)	0.0262 (12)	0.0116 (10)	0.0025 (9)	0.0010 (8)	0.0051 (9)
C1	0.0199 (12)	0.0205 (13)	0.0150 (11)	−0.0018 (10)	−0.0008 (9)	0.0033 (10)
C2	0.0167 (12)	0.0184 (12)	0.0179 (12)	−0.0009 (9)	0.0010 (9)	0.0035 (10)
C3	0.0193 (12)	0.0214 (13)	0.0193 (12)	−0.0009 (10)	−0.0028 (10)	0.0067 (10)
C4	0.0242 (13)	0.0231 (13)	0.0141 (11)	−0.0049 (10)	−0.0038 (10)	0.0067 (10)
C5	0.0227 (13)	0.0231 (13)	0.0141 (12)	−0.0035 (10)	0.0020 (10)	0.0021 (10)
C6	0.0172 (12)	0.0178 (12)	0.0165 (12)	−0.0023 (9)	0.0003 (9)	0.0037 (10)
C7	0.0180 (12)	0.0178 (12)	0.0219 (12)	0.0009 (10)	0.0031 (10)	0.0062 (10)
C8	0.0210 (12)	0.0194 (12)	0.0166 (12)	0.0011 (10)	0.0013 (10)	0.0039 (10)
C9	0.0185 (12)	0.0175 (12)	0.0171 (12)	0.0023 (10)	0.0020 (9)	0.0042 (10)
C10	0.0187 (12)	0.0246 (13)	0.0155 (12)	0.0009 (10)	−0.0006 (9)	0.0028 (10)
C11	0.0250 (13)	0.0286 (14)	0.0143 (12)	0.0030 (11)	0.0002 (10)	0.0074 (10)
C12	0.0188 (12)	0.0238 (13)	0.0193 (12)	0.0036 (10)	0.0032 (10)	0.0087 (10)
C13	0.0160 (12)	0.0194 (12)	0.0201 (12)	0.0037 (9)	0.0018 (9)	0.0074 (10)
C14	0.0180 (12)	0.0239 (13)	0.0181 (12)	0.0014 (10)	0.0003 (10)	0.0059 (10)
C15	0.0194 (12)	0.0185 (12)	0.0158 (12)	−0.0035 (10)	0.0001 (9)	0.0031 (10)
C16	0.0225 (13)	0.0246 (13)	0.0195 (12)	0.0042 (11)	−0.0009 (10)	0.0056 (10)
C17	0.0197 (12)	0.0216 (13)	0.0227 (13)	0.0003 (10)	−0.0019 (10)	0.0062 (10)
C18	0.0381 (16)	0.0293 (15)	0.0149 (12)	0.0067 (12)	0.0010 (11)	0.0024 (11)
O1W	0.0284 (10)	0.0249 (10)	0.0216 (9)	0.0065 (8)	−0.0015 (8)	0.0052 (8)
O2W	0.0354 (11)	0.0256 (10)	0.0246 (10)	−0.0025 (9)	0.0084 (8)	0.0027 (8)
O3W	0.0351 (12)	0.0370 (12)	0.0304 (11)	0.0082 (10)	−0.0113 (9)	−0.0037 (9)
O4W	0.0845 (19)	0.0357 (13)	0.0170 (10)	−0.0282 (12)	0.0008 (11)	0.0061 (9)

Geometric parameters (Å, º) top

Co1—N1	2.029 (2)	C3—H3B	0.9500
Co1—N2	2.031 (2)	C4—C5	1.390 (4)
Co1—O8	2.1273 (18)	C4—H4A	0.9500
Co1—O4	2.1389 (18)	C5—C6	1.394 (3)
Co1—O5	2.1904 (18)	C5—H5C	0.9500
Co1—O1	2.2239 (19)	C6—C7	1.509 (3)
O1—C1	1.273 (3)	C8—C9	1.511 (3)
O2—C1	1.245 (3)	C9—C10	1.387 (3)
O3—C7	1.233 (3)	C10—C11	1.386 (4)
O4—C7	1.283 (3)	C10—H10A	0.9500
O5—C8	1.268 (3)	C11—C12	1.388 (4)
O6—C8	1.249 (3)	C11—H11A	0.9500
O7—C14	1.247 (3)	C12—C13	1.392 (3)
O8—C14	1.263 (3)	C12—H12A	0.9500
O9—C17	1.215 (3)	C13—C14	1.516 (3)
N1—C6	1.325 (3)	C16—C17	1.509 (4)
N1—C2	1.338 (3)	C16—H16A	0.9900
N2—C9	1.334 (3)	C16—H16B	0.9900
N2—C13	1.335 (3)	C18—H18A	0.9800
N3—C15	1.370 (3)	C18—H18B	0.9800
N3—C17	1.371 (3)	C18—H18C	0.9800
N3—H3A	0.8800	O1W—H1	0.8500
N4—C15	1.331 (3)	O1W—H2	0.8500
N4—C18	1.458 (3)	O2W—H3	0.8500
N4—C16	1.459 (3)	O2W—H4	0.8500
N5—C15	1.301 (3)	O2W—H5	0.8500
N5—H5A	0.8800	O3W—H6	0.8500
N5—H5B	0.8800	O3W—H7	0.8500
C1—C2	1.507 (3)	O4W—H8	0.8500
C2—C3	1.391 (3)	O4W—H9	0.8500
C3—C4	1.397 (4)

N1—Co1—N2	171.90 (8)	N1—C6—C7	113.5 (2)
N1—Co1—O8	104.11 (7)	C5—C6—C7	125.5 (2)
N2—Co1—O8	76.44 (7)	O3—C7—O4	126.1 (2)
N1—Co1—O4	77.02 (8)	O3—C7—C6	118.5 (2)
N2—Co1—O4	111.08 (8)	O4—C7—C6	115.4 (2)
O8—Co1—O4	88.59 (7)	O6—C8—O5	126.3 (2)
N1—Co1—O5	104.55 (7)	O6—C8—C9	117.6 (2)
N2—Co1—O5	75.49 (7)	O5—C8—C9	116.1 (2)
O8—Co1—O5	151.26 (7)	N2—C9—C10	121.4 (2)
O4—Co1—O5	95.77 (7)	N2—C9—C8	112.8 (2)
N1—Co1—O1	75.10 (7)	C10—C9—C8	125.8 (2)
N2—Co1—O1	96.82 (7)	C11—C10—C9	118.0 (2)
O8—Co1—O1	99.21 (7)	C11—C10—H10A	121.0
O4—Co1—O1	152.09 (7)	C9—C10—H10A	121.0
O5—Co1—O1	90.12 (7)	C10—C11—C12	120.4 (2)
C1—O1—Co1	115.11 (16)	C10—C11—H11A	119.8
C7—O4—Co1	114.49 (16)	C12—C11—H11A	119.8
C8—O5—Co1	115.09 (16)	C11—C12—C13	118.1 (2)
C14—O8—Co1	116.51 (16)	C11—C12—H12A	121.0
C6—N1—C2	121.3 (2)	C13—C12—H12A	121.0
C6—N1—Co1	118.26 (17)	N2—C13—C12	120.9 (2)
C2—N1—Co1	120.43 (16)	N2—C13—C14	112.3 (2)
C9—N2—C13	121.1 (2)	C12—C13—C14	126.8 (2)
C9—N2—Co1	119.81 (16)	O7—C14—O8	125.7 (2)
C13—N2—Co1	118.89 (16)	O7—C14—C13	118.6 (2)
C15—N3—C17	110.3 (2)	O8—C14—C13	115.6 (2)
C15—N3—H3A	124.8	N5—C15—N4	126.3 (2)
C17—N3—H3A	124.8	N5—C15—N3	123.3 (2)
C15—N4—C18	125.2 (2)	N4—C15—N3	110.4 (2)
C15—N4—C16	110.1 (2)	N4—C16—C17	102.3 (2)
C18—N4—C16	123.7 (2)	N4—C16—H16A	111.3
C15—N5—H5A	120.0	C17—C16—H16A	111.3
C15—N5—H5B	120.0	N4—C16—H16B	111.3
H5A—N5—H5B	120.0	C17—C16—H16B	111.3
O2—C1—O1	126.4 (2)	H16A—C16—H16B	109.2
O2—C1—C2	118.0 (2)	O9—C17—N3	125.7 (2)
O1—C1—C2	115.6 (2)	O9—C17—C16	127.5 (2)
N1—C2—C3	121.2 (2)	N3—C17—C16	106.8 (2)
N1—C2—C1	113.7 (2)	N4—C18—H18A	109.5
C3—C2—C1	125.1 (2)	N4—C18—H18B	109.5
C2—C3—C4	118.3 (2)	H18A—C18—H18B	109.5
C2—C3—H3B	120.9	N4—C18—H18C	109.5
C4—C3—H3B	120.9	H18A—C18—H18C	109.5
C5—C4—C3	119.4 (2)	H18B—C18—H18C	109.5
C5—C4—H4A	120.3	H1—O1W—H2	105.5
C3—C4—H4A	120.3	H3—O2W—H4	106.0
C4—C5—C6	118.7 (2)	H3—O2W—H5	110.2
C4—C5—H5C	120.6	H4—O2W—H5	109.9
C6—C5—H5C	120.6	H6—O3W—H7	110.0
N1—C6—C5	121.0 (2)	H8—O4W—H9	108.1

N1—Co1—O1—C1	2.34 (17)	C2—N1—C6—C5	−1.7 (4)
N2—Co1—O1—C1	−178.09 (18)	Co1—N1—C6—C5	179.89 (18)
O8—Co1—O1—C1	104.61 (18)	C2—N1—C6—C7	177.0 (2)
O4—Co1—O1—C1	0.0 (3)	Co1—N1—C6—C7	−1.4 (3)
O5—Co1—O1—C1	−102.69 (18)	C4—C5—C6—N1	0.7 (4)
N1—Co1—O4—C7	9.68 (17)	C4—C5—C6—C7	−177.8 (2)
N2—Co1—O4—C7	−170.03 (17)	Co1—O4—C7—O3	164.3 (2)
O8—Co1—O4—C7	−95.15 (17)	Co1—O4—C7—C6	−13.2 (3)
O5—Co1—O4—C7	113.32 (17)	N1—C6—C7—O3	−167.8 (2)
O1—Co1—O4—C7	12.1 (3)	C5—C6—C7—O3	10.9 (4)
N1—Co1—O5—C8	−164.94 (17)	N1—C6—C7—O4	10.0 (3)
N2—Co1—O5—C8	6.69 (17)	C5—C6—C7—O4	−171.4 (2)
O8—Co1—O5—C8	19.4 (3)	Co1—O5—C8—O6	177.3 (2)
O4—Co1—O5—C8	117.01 (18)	Co1—O5—C8—C9	−4.7 (3)
O1—Co1—O5—C8	−90.32 (18)	C13—N2—C9—C10	1.5 (4)
N1—Co1—O8—C14	172.30 (18)	Co1—N2—C9—C10	−173.89 (18)
N2—Co1—O8—C14	0.63 (18)	C13—N2—C9—C8	−176.7 (2)
O4—Co1—O8—C14	−111.46 (19)	Co1—N2—C9—C8	7.9 (3)
O5—Co1—O8—C14	−12.0 (3)	O6—C8—C9—N2	176.6 (2)
O1—Co1—O8—C14	95.48 (19)	O5—C8—C9—N2	−1.6 (3)
O8—Co1—N1—C6	81.22 (18)	O6—C8—C9—C10	−1.5 (4)
O4—Co1—N1—C6	−3.96 (17)	O5—C8—C9—C10	−179.7 (2)
O5—Co1—N1—C6	−96.65 (18)	N2—C9—C10—C11	−1.1 (4)
O1—Co1—N1—C6	177.18 (19)	C8—C9—C10—C11	176.9 (2)
O8—Co1—N1—C2	−97.19 (19)	C9—C10—C11—C12	−0.4 (4)
O4—Co1—N1—C2	177.62 (19)	C10—C11—C12—C13	1.3 (4)
O5—Co1—N1—C2	84.94 (19)	C9—N2—C13—C12	−0.5 (4)
O1—Co1—N1—C2	−1.23 (17)	Co1—N2—C13—C12	174.95 (18)
O8—Co1—N2—C9	178.3 (2)	C9—N2—C13—C14	179.3 (2)
O4—Co1—N2—C9	−98.58 (19)	Co1—N2—C13—C14	−5.2 (3)
O5—Co1—N2—C9	−7.92 (18)	C11—C12—C13—N2	−0.9 (4)
O1—Co1—N2—C9	80.44 (19)	C11—C12—C13—C14	179.3 (2)
O8—Co1—N2—C13	2.82 (17)	Co1—O8—C14—O7	175.7 (2)
O4—Co1—N2—C13	85.92 (19)	Co1—O8—C14—C13	−3.5 (3)
O5—Co1—N2—C13	176.59 (19)	N2—C13—C14—O7	−173.6 (2)
O1—Co1—N2—C13	−95.06 (18)	C12—C13—C14—O7	6.2 (4)
Co1—O1—C1—O2	176.8 (2)	N2—C13—C14—O8	5.6 (3)
Co1—O1—C1—C2	−3.0 (3)	C12—C13—C14—O8	−174.6 (2)
C6—N1—C2—C3	1.2 (4)	C18—N4—C15—N5	−11.3 (4)
Co1—N1—C2—C3	179.52 (18)	C16—N4—C15—N5	−179.8 (2)
C6—N1—C2—C1	−178.2 (2)	C18—N4—C15—N3	168.9 (2)
Co1—N1—C2—C1	0.2 (3)	C16—N4—C15—N3	0.4 (3)
O2—C1—C2—N1	−177.8 (2)	C17—N3—C15—N5	178.5 (2)
O1—C1—C2—N1	2.0 (3)	C17—N3—C15—N4	−1.7 (3)
O2—C1—C2—C3	2.9 (4)	C15—N4—C16—C17	0.9 (3)
O1—C1—C2—C3	−177.4 (2)	C18—N4—C16—C17	−167.8 (2)
N1—C2—C3—C4	0.4 (4)	C15—N3—C17—O9	−179.0 (3)
C1—C2—C3—C4	179.6 (2)	C15—N3—C17—C16	2.2 (3)
C2—C3—C4—C5	−1.3 (4)	N4—C16—C17—O9	179.4 (3)
C3—C4—C5—C6	0.8 (4)	N4—C16—C17—N3	−1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Wⁱ	0.88	1.86	2.716 (3)	164
N5—H5A···O5	0.88	2.15	2.882 (3)	141
N5—H5B···O3ⁱⁱ	0.88	1.96	2.764 (3)	152
O1W—H1···O4ⁱⁱⁱ	0.85	1.95	2.782 (3)	166
O1W—H2···O3W^iv	0.85	1.85	2.673 (3)	164
O2W—H3···O4W^v	0.85	1.70	2.522 (3)	163
O2W—H4···O6^vi	0.85	1.64	2.481 (3)	170
O2W—H5···O2	0.85	1.71	2.537 (3)	164
O3W—H6···O7ⁱⁱⁱ	0.85	1.93	2.778 (3)	172
O3W—H7···O9^vii	0.85	2.22	2.948 (3)	144
O4W—H8···O7^viii	0.85	1.84	2.680 (3)	169
O4W—H9···O1	0.85	1.87	2.718 (3)	172
C3—H3B···O9^vii	0.95	2.37	3.301 (3)	165
C4—H4A···O8^ix	0.95	2.43	3.252 (3)	145
C18—H18C···O7ⁱⁱⁱ	0.98	2.60	3.535 (4)	160

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x, y−1, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z; (vi) x+1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+2, −z; (ix) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	(C₄H₈N₃O)(H₃O)[Co(C₇H₃NO₄)₂]·3H₂O
M_r	576.34
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.0937 (10), 10.7389 (13), 13.5976 (17)
α, β, γ (°)	104.811 (2), 90.267 (2), 92.415 (1)
V (Å³)	1141.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.18 × 0.12 × 0.09

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.889, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	11652, 5488, 4149
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.097, 1.02
No. of reflections	5488
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.45

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Selected bond lengths (Å) top

Co1—N1	2.029 (2)	Co1—O4	2.1389 (18)
Co1—N2	2.031 (2)	Co1—O5	2.1904 (18)
Co1—O8	2.1273 (18)	Co1—O1	2.2239 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Wⁱ	0.88	1.859	2.716 (3)	164
N5—H5A···O5	0.88	2.148	2.882 (3)	141
N5—H5B···O3ⁱⁱ	0.88	1.956	2.764 (3)	152
O1W—H1···O4ⁱⁱⁱ	0.85	1.949	2.782 (3)	166
O1W—H2···O3W^iv	0.85	1.845	2.673 (3)	164
O2W—H3···O4W^v	0.85	1.697	2.522 (3)	163
O2W—H4···O6^vi	0.85	1.640	2.481 (3)	170
O2W—H5···O2	0.85	1.710	2.537 (3)	164
O3W—H6···O7ⁱⁱⁱ	0.85	1.934	2.778 (3)	172
O3W—H7···O9^vii	0.85	2.216	2.948 (3)	144
O4W—H8···O7^viii	0.85	1.840	2.680 (3)	169
O4W—H9···O1	0.85	1.874	2.718 (3)	172
C3—H3B···O9^vii	0.95	2.37	3.301 (3)	165
C4—H4A···O8^ix	0.95	2.43	3.252 (3)	145
C18—H18C···O7ⁱⁱⁱ	0.98	2.60	3.535 (4)	160

References

Aghabozorg, H., Derikvand, Z., Olmstead, M. M. & Attar Gharamaleki, J. (2008). Acta Cryst. E64, m1234–m1235. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Aghabozorg, H., Ramezanipour, F., Sleimannejad, J., Sharif, M. A., Shokrollahi, A., Shamsipur, M., Moghimi, A., Attar Gharamaleki, J., Lippolis, V. & Blake, A. (2008). Pol. J. Chem. 82, 487–507. CAS Google Scholar
Attar Gharamaleki, J., Aghabozorg, H., Derikvand, Z. & Yousefi, M. (2009). Acta Cryst. E65, m824–m825. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2007). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Moghimi, A., Sharif, M. A. & Aghabozorg, H. (2004). Acta Cryst. E60, o1790–o1792. Web of Science CSD CrossRef IUCr Journals Google Scholar
Moghimi, A., Sharif, M. A., Shokrollahi, A., Shamsipur, M. & Aghabozorg, H. (2005). Z. Anorg. Allg. Chem. 631, 902–908. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 7| July 2009| Pages m826-m827

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