3,5-Diamino-4H-1,2,4-triazol-1-ium hydroxonium bis­(pyridine-2,6-di­carboxyl­ato)cobaltate(II) pyridine-2,6-dicarb­oxy­lic acid monohydrate

Yousuf, S.; Johnson, A.S.; Kazmi, S.A.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536811027917

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1105-m1106

doi:10.1107/S1600536811027917

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3,5-Diamino-4H-1,2,4-triazol-1-ium hydroxonium bis(pyridine-2,6-dicarboxylato)cobaltate(II) pyridine-2,6-dicarboxylic acid monohydrate

S. Yousuf,^a A. S. Johnson,^b S. A. Kazmi,^a Madhukar Hemamalini ^c and Hoong-Kun Fun ^c ^*‡

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi 75270, Pakistan, ^bDepartment of Pure and Applied Chemistry, University of Calabar, Calabar, PMB 1115, Nigeria, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 4 July 2011; accepted 12 July 2011; online 16 July 2011)

The asymmetric unit of the title complex, (C₂H₆N₅)(H₃O)[Co(C₇H₃NO₄)₂]·C₇H₅NO₄·H₂O, contains a Co^II ion coordinated by four O atoms and two N atoms from two dipicolinate ligands in a disorted octahedral environment, a protonated triazole molecule, a neutral pyridine-2,6-dicarboxylic acid molecule, a hydroxonium ion and a solvent water molecule. In the crystal, the components are linked into a three-dimensional framework by intermolecular O—H⋯O, N—H⋯O and N—H⋯N and weak C—H⋯O hydrogen bonds. In addition, π–π stacking interactions with centroid–centroid distances in the range 3.4809 (7)–3.8145 (6) Å are observed.

Related literature

For the different coordination modes for transition metal–dipicolinate complexes, see: Quaglieri et al. (1972 ); Hakansson et al. (1993 ); Okabe & Oya (2000 ); Aghajani et al. (2009 ). For crystal structures of related complexes, see: Yousuf et al. (2011 ); Aghabozorg et al. (2009 ); Ramos Silva et al. (2008 ); Wang et al. (2004 ); MacDonald et al. (2000 , 2004 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

(C₂H₆N₅)(H₃O)[Co(C₇H₃NO₄)₂]·C₇H₅NO₄·H₂O
M_r = 693.42
Triclinic, $[P \overline 1]$
a = 8.0209 (2) Å
b = 9.2028 (2) Å
c = 18.7004 (4) Å
α = 98.536 (1)°
β = 96.721 (1)°
γ = 100.515 (1)°
V = 1327.32 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 100 K
0.78 × 0.59 × 0.35 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.595, T_max = 0.781
25547 measured reflections
7698 independent reflections
7360 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.072
S = 1.05
7698 reflections
467 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O10ⁱ	0.841 (19)	2.249 (18)	3.0304 (15)	154.5 (17)
N3—H1N3⋯N8ⁱ	0.841 (19)	2.47 (2)	3.1379 (15)	136.5 (16)
N3—H2N3⋯O11ⁱ	0.86 (2)	2.28 (2)	2.9563 (15)	135.7 (17)
N4—H1N4⋯O2	0.85 (2)	2.072 (19)	2.9084 (14)	169 (2)
N4—H2N4⋯O1W	0.85 (2)	1.96 (2)	2.8057 (16)	172 (2)
N6—H1N6⋯O3ⁱⁱ	0.877 (18)	1.870 (18)	2.7368 (12)	169.7 (16)
N7—H1N7⋯O7	0.85 (2)	1.89 (2)	2.7245 (13)	167 (2)
O10—H1OA⋯O7ⁱ	0.79 (2)	1.86 (2)	2.5775 (13)	152 (3)
O1W—H1W1⋯O6ⁱⁱⁱ	0.78 (2)	2.06 (2)	2.8315 (14)	172 (2)
O1W—H2W1⋯O1ⁱⁱ	0.82 (3)	2.23 (3)	2.8901 (14)	138 (2)
O2W—H2W2⋯O8^iv	0.87 (3)	1.67 (2)	2.5279 (13)	170 (2)
O2W—H1W2⋯O5^v	0.98 (3)	1.48 (3)	2.4622 (13)	177 (3)
O2W—H3W2⋯O6ⁱⁱ	0.87 (2)	1.71 (2)	2.5746 (13)	174 (2)
O12—H12B⋯N5^vi	0.89 (2)	1.76 (2)	2.6303 (14)	169 (2)
C3—H3A⋯O9^vii	0.95	2.52	3.1725 (14)	126
C5—H5A⋯O9ⁱ	0.95	2.59	3.5380 (15)	175
C10—H10A⋯O1^viii	0.95	2.38	3.2669 (14)	156
C19—H19A⋯O2W	0.95	2.50	3.4269 (15)	165
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y-1, z; (iii) -x+1, -y+1, -z; (iv) x+1, y-1, z; (v) x+1, y, z; (vi) x, y+1, z; (vii) x-1, y+1, z; (viii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027917/lh5282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027917/lh5282Isup2.hkl

checkCIF report

Comment top

Pyridine-2,6 dicarboxylic acid (H2dipic) and its anions (dipic^2- & dipicH^-) have been identified to be well suited for the construction of multidimensional frameworks with simple metal ions and non-metal cations due to the presence of heterocyclic nitrogen atoms and two carboxylate groups. A range of different coordination modes exists in transition metal-dipicolinate complexes (Quaglieri et al., 1972, Hakansson et al., 1993, Okabe & Oya, 2000) depending on whether the anionic or protonated forms of the carboxylates are coordinated to the metal ion. It has been observed that providing suitable conditions for the transfer of acidic protons to appropriate bases will result in increased intermolecular interactions and stabilization of the resulting system (Aghajani et al., 2009). In recent work on the study of the structural features of molecules containing metal chelate and triazole rings, we have determined the crystal structure of a Cu(II) with a derivative of 1,2,4-triazole and dipicolinic acid (Yousuf et al., 2011). Herein, we report the crystal structure of the title complex (I).

The asymmetric unit of (I) is shown in Fig. 1. It contains a Co^II ion, two tridentate dipicolinte ligands, a protonated triazole molecule, a neutral pyridine 2,6-dicarboxylic acid molecule, a hydroxonium ion and a solvent water molecule. The Co^II ion is in a distorted octahedral coordination environment formed by four oxygen atoms and two nitrogen atoms from two dipicolinate ligands. The two dipiconilate ligands are assembled approximately perpendicular to each other around the Co^II ion with atoms O3 and O4 in the axial sites and atoms N1/N2/O1/O2 forming the equatorial sites. All bond lengths are in agreement with those common to related structures (Yousuf et al., 2011; Aghabozorg et al., 2009; Ramos Silva et al., 2008; Wang et al., 2004; MacDonald et al., 2000,2004).

In the crystal structure (Fig. 2), intermolecular O—H···O, N—H···O, N—H···N and weak C—H···O (Table 1) hydrogen bonds form a three-dimensional network. The network is further stabilized by π–π stacking interactions between the centroids of Co1/O2/N1/C6/C7 (Cg1), Co1/O3/N2/C13/C14 (Cg2), N1/C2–C6 (Cg3), N2/C9–C13 (Cg4), N8/C17–C21 (Cg5) and N5–N7/C15/C16 (Cg6) rings, with Cg1···Cg5ⁱ, Cg2···Cg4ⁱⁱ, Cg3···Cg5ⁱⁱⁱ, Cg3···Cg6^iv and Cg4···Cg4^v, distances of 3.6235 (6) Å, 3.8145 (6) Å, 3.7500 (7) Å, 3.5247 (7) Å and 3.4809 (7) Å, respectively [symmetry codes: (i) -1+x, y, z; (ii) 1-x, 1-y, -z; (iii) -1+x, y, z; (iv) x, -1+y, z; (v) -x, 1-y, -z].

Related literature top

For the different coordination modes for transition metal–dipicolinate complexes, see: Quaglieri et al. (1972); Hakansson et al. (1993); Okabe & Oya (2000); Aghajani et al. (2009). For crystal structures of related complexes, see: Yousuf et al. (2011); Aghabozorg et al. (2009); Ramos Silva et al. (2008); Wang et al. (2004); MacDonald et al. (2000, 2004). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Pyridine-2,6-dicarboxylic acid and 3,5-diamino-1,2,4-triazole were purchased from Merck and Molekula respectively. Cobaltchloride hexahydrate (CoCl₂.6H₂O) and HPLC grade methanol were Uni-Chem and M TEDIA products, respectively. Deionized water was also used in the procedures when needed.

A method similar to that reported by Yousuf et al. (2011) was used. 1 mmol (0.099 g) of 3,5-diamino- 1,2,4-triazole and 1 mmol of dipicolinic acid (0.167 g) were dissolved in a mixture of methanol/water solution (1:10, 11 ml). The resulting solution was heated to 338 K with stirring. An aqueous solution (1 ml) containing 0.5 mmol (0.119 g) of CoCl₂.6H₂O was added to the stirred solution. The redish purple suspension was allowed to stir further for 1 hr, and then filtered while hot. The filtrate was kept at room temperature. Well shaped purple crystals of the title compound were formed by slow evaporation of the solution after 2 weeks. Percentage yield based on cobalt is 46.34%.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound, showing hydrogen bonds as dashed lines.

3,5-Diamino-4H-1,2,4-triazol-1-ium hydroxonium bis(pyridine-2,6-dicarboxylato)cobaltate(II) pyridine-2,6-dicarboxylic acid monohydrate top

Crystal data top

(C₂H₆N₅)(H₃O)[Co(C₇H₃NO₄)₂]·C₇H₅NO₄·H₂O	Z = 2
M_r = 693.42	F(000) = 710
Triclinic, P1	D_x = 1.735 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0209 (2) Å	Cell parameters from 9943 reflections
b = 9.2028 (2) Å	θ = 2.9–35.1°
c = 18.7004 (4) Å	µ = 0.74 mm⁻¹
α = 98.536 (1)°	T = 100 K
β = 96.721 (1)°	Block, purple
γ = 100.515 (1)°	0.78 × 0.59 × 0.35 mm
V = 1327.32 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7698 independent reflections
Radiation source: fine-focus sealed tube	7360 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.595, T_max = 0.781	k = −12→12
25547 measured reflections	l = −26→26

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0325P)² + 0.8694P] where P = (F_o² + 2F_c²)/3
7698 reflections	(Δ/σ)_max = 0.001
467 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

(C₂H₆N₅)(H₃O)[Co(C₇H₃NO₄)₂]·C₇H₅NO₄·H₂O	γ = 100.515 (1)°
M_r = 693.42	V = 1327.32 (5) Å³
Triclinic, P1	Z = 2
a = 8.0209 (2) Å	Mo Kα radiation
b = 9.2028 (2) Å	µ = 0.74 mm⁻¹
c = 18.7004 (4) Å	T = 100 K
α = 98.536 (1)°	0.78 × 0.59 × 0.35 mm
β = 96.721 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7698 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7360 reflections with I > 2σ(I)
T_min = 0.595, T_max = 0.781	R_int = 0.018
25547 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.48 e Å⁻³
7698 reflections	Δρ_min = −0.43 e Å⁻³
467 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.302228 (19)	0.644423 (16)	0.169857 (8)	0.01036 (5)
N1	0.31342 (12)	0.75361 (10)	0.27349 (5)	0.01027 (16)
N2	0.30641 (12)	0.58813 (10)	0.06050 (5)	0.01004 (16)
O1	0.13428 (11)	0.80434 (9)	0.15754 (4)	0.01381 (15)
O2	0.45499 (11)	0.52726 (9)	0.23827 (4)	0.01373 (15)
O3	0.52409 (11)	0.80151 (9)	0.14717 (4)	0.01281 (15)
O4	0.12604 (11)	0.43393 (9)	0.13837 (5)	0.01510 (16)
O5	0.00050 (11)	0.25528 (9)	0.04207 (5)	0.01481 (16)
O6	0.63852 (12)	0.88973 (10)	0.05403 (5)	0.01749 (17)
O7	0.54563 (11)	0.51915 (9)	0.35540 (5)	0.01517 (16)
O8	0.06823 (12)	1.00920 (10)	0.22102 (5)	0.01651 (16)
C1	0.13704 (14)	0.89743 (12)	0.21521 (6)	0.01192 (19)
C2	0.23804 (14)	0.87158 (12)	0.28416 (6)	0.01092 (18)
C3	0.25593 (15)	0.95939 (12)	0.35273 (6)	0.01309 (19)
H3A	0.2025	1.0434	0.3598	0.016*
C4	0.35408 (15)	0.92139 (13)	0.41088 (6)	0.0138 (2)
H4A	0.3688	0.9801	0.4583	0.017*
C5	0.43087 (15)	0.79723 (12)	0.39962 (6)	0.01307 (19)
H5A	0.4972	0.7692	0.4388	0.016*
C6	0.40713 (14)	0.71590 (12)	0.32909 (6)	0.01085 (18)
C7	0.47660 (14)	0.57714 (12)	0.30615 (6)	0.01145 (19)
C8	0.09977 (14)	0.37796 (12)	0.07162 (6)	0.01156 (19)
C9	0.19911 (13)	0.46510 (12)	0.02260 (6)	0.01047 (18)
C10	0.19089 (14)	0.42474 (12)	−0.05245 (6)	0.01231 (19)
H10A	0.1149	0.3366	−0.0788	0.015*
C11	0.29789 (15)	0.51793 (13)	−0.08794 (6)	0.0145 (2)
H11A	0.2944	0.4944	−0.1394	0.017*
C12	0.41009 (15)	0.64579 (13)	−0.04790 (6)	0.0135 (2)
H12A	0.4835	0.7103	−0.0714	0.016*
C13	0.41151 (14)	0.67618 (12)	0.02725 (6)	0.01103 (18)
C14	0.53451 (14)	0.80151 (12)	0.07972 (6)	0.01191 (19)
O9	1.31990 (13)	0.28490 (10)	0.44827 (5)	0.01975 (18)
O10	1.29486 (12)	0.49673 (10)	0.51898 (5)	0.01785 (17)
O11	0.93965 (12)	0.82190 (10)	0.44184 (5)	0.01879 (17)
O12	0.83933 (12)	0.78120 (10)	0.32170 (5)	0.01702 (17)
N8	1.08308 (12)	0.56516 (10)	0.41642 (5)	0.01197 (17)
C17	0.97897 (14)	0.60148 (12)	0.36347 (6)	0.01172 (19)
C18	0.92791 (15)	0.51390 (13)	0.29409 (6)	0.0144 (2)
H18A	0.8533	0.5439	0.2583	0.017*
C19	0.98785 (16)	0.38218 (13)	0.27808 (6)	0.0150 (2)
H19A	0.9538	0.3196	0.2315	0.018*
C20	1.09842 (15)	0.34425 (12)	0.33159 (6)	0.0144 (2)
H20A	1.1440	0.2562	0.3223	0.017*
C21	1.14112 (14)	0.43846 (12)	0.39946 (6)	0.01212 (19)
C22	1.26029 (15)	0.39687 (13)	0.45743 (6)	0.0139 (2)
C23	0.91764 (14)	0.74663 (12)	0.38133 (6)	0.01276 (19)
N3	0.79103 (15)	0.19736 (13)	0.43972 (6)	0.0187 (2)
N4	0.47746 (15)	0.21239 (12)	0.21219 (6)	0.0187 (2)
N5	0.72357 (13)	0.03157 (11)	0.32639 (5)	0.01330 (18)
N6	0.62946 (13)	0.03978 (11)	0.25973 (5)	0.01312 (17)
N7	0.62630 (13)	0.24252 (11)	0.33308 (5)	0.01265 (17)
C15	0.57107 (15)	0.16592 (12)	0.26417 (6)	0.01257 (19)
C16	0.71983 (14)	0.15723 (12)	0.36943 (6)	0.01230 (19)
O1W	0.29638 (15)	0.03156 (12)	0.08229 (6)	0.0269 (2)
O2W	0.87798 (12)	0.10223 (10)	0.12792 (5)	0.01508 (16)
H1N3	0.795 (2)	0.285 (2)	0.4615 (11)	0.027 (5)*
H2N3	0.863 (3)	0.147 (2)	0.4562 (11)	0.036 (5)*
H1N4	0.457 (3)	0.300 (2)	0.2214 (11)	0.033 (5)*
H2N4	0.430 (3)	0.152 (2)	0.1733 (11)	0.027 (5)*
H1N6	0.609 (2)	−0.036 (2)	0.2233 (10)	0.024 (4)*
H1N7	0.605 (3)	0.328 (2)	0.3472 (11)	0.031 (5)*
H1OA	1.351 (3)	0.468 (3)	0.5490 (12)	0.041 (6)*
H12B	0.806 (3)	0.868 (2)	0.3295 (11)	0.036 (5)*
H1W1	0.306 (3)	0.047 (3)	0.0429 (13)	0.043 (6)*
H2W1	0.218 (3)	−0.039 (3)	0.0821 (12)	0.039 (6)*
H2W2	0.947 (3)	0.065 (3)	0.1557 (13)	0.044 (6)*
H1W2	0.930 (4)	0.165 (3)	0.0952 (16)	0.079 (9)*
H3W2	0.796 (3)	0.028 (2)	0.1059 (12)	0.036 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01302 (7)	0.00984 (7)	0.00789 (7)	0.00244 (5)	0.00097 (5)	0.00086 (5)
N1	0.0119 (4)	0.0096 (4)	0.0093 (4)	0.0025 (3)	0.0011 (3)	0.0019 (3)
N2	0.0109 (4)	0.0096 (4)	0.0093 (4)	0.0019 (3)	0.0007 (3)	0.0013 (3)
O1	0.0170 (4)	0.0134 (4)	0.0104 (4)	0.0044 (3)	−0.0007 (3)	0.0008 (3)
O2	0.0183 (4)	0.0124 (4)	0.0110 (4)	0.0059 (3)	0.0014 (3)	0.0010 (3)
O3	0.0158 (4)	0.0112 (3)	0.0099 (3)	0.0005 (3)	0.0005 (3)	0.0007 (3)
O4	0.0187 (4)	0.0136 (4)	0.0113 (4)	−0.0010 (3)	0.0022 (3)	0.0020 (3)
O5	0.0165 (4)	0.0115 (4)	0.0142 (4)	−0.0016 (3)	0.0001 (3)	0.0023 (3)
O6	0.0186 (4)	0.0165 (4)	0.0138 (4)	−0.0050 (3)	0.0013 (3)	0.0030 (3)
O7	0.0203 (4)	0.0137 (4)	0.0125 (4)	0.0080 (3)	−0.0011 (3)	0.0025 (3)
O8	0.0218 (4)	0.0152 (4)	0.0144 (4)	0.0098 (3)	−0.0002 (3)	0.0033 (3)
C1	0.0130 (5)	0.0119 (5)	0.0110 (5)	0.0025 (4)	0.0006 (4)	0.0034 (4)
C2	0.0126 (4)	0.0104 (4)	0.0101 (4)	0.0030 (4)	0.0013 (4)	0.0026 (4)
C3	0.0168 (5)	0.0111 (4)	0.0118 (5)	0.0048 (4)	0.0020 (4)	0.0011 (4)
C4	0.0180 (5)	0.0126 (5)	0.0104 (5)	0.0038 (4)	0.0013 (4)	0.0003 (4)
C5	0.0160 (5)	0.0130 (5)	0.0103 (5)	0.0043 (4)	0.0000 (4)	0.0023 (4)
C6	0.0129 (4)	0.0096 (4)	0.0104 (4)	0.0027 (4)	0.0016 (4)	0.0024 (3)
C7	0.0123 (4)	0.0104 (4)	0.0118 (5)	0.0031 (4)	0.0010 (4)	0.0022 (4)
C8	0.0114 (4)	0.0111 (4)	0.0125 (5)	0.0026 (4)	0.0007 (4)	0.0034 (4)
C9	0.0098 (4)	0.0104 (4)	0.0111 (5)	0.0025 (3)	0.0009 (3)	0.0016 (3)
C10	0.0120 (5)	0.0124 (5)	0.0112 (5)	0.0020 (4)	−0.0002 (4)	−0.0001 (4)
C11	0.0156 (5)	0.0172 (5)	0.0097 (5)	0.0024 (4)	0.0013 (4)	0.0011 (4)
C12	0.0143 (5)	0.0151 (5)	0.0108 (5)	0.0012 (4)	0.0019 (4)	0.0029 (4)
C13	0.0110 (4)	0.0104 (4)	0.0110 (5)	0.0014 (4)	0.0008 (4)	0.0013 (3)
C14	0.0128 (5)	0.0106 (4)	0.0112 (5)	0.0014 (4)	0.0004 (4)	0.0009 (4)
O9	0.0265 (5)	0.0157 (4)	0.0186 (4)	0.0114 (3)	0.0001 (3)	0.0019 (3)
O10	0.0241 (4)	0.0166 (4)	0.0129 (4)	0.0101 (3)	−0.0040 (3)	0.0006 (3)
O11	0.0241 (4)	0.0176 (4)	0.0149 (4)	0.0096 (3)	−0.0003 (3)	−0.0005 (3)
O12	0.0231 (4)	0.0135 (4)	0.0149 (4)	0.0088 (3)	−0.0028 (3)	0.0020 (3)
N8	0.0135 (4)	0.0112 (4)	0.0117 (4)	0.0038 (3)	0.0014 (3)	0.0022 (3)
C17	0.0130 (5)	0.0109 (4)	0.0114 (5)	0.0032 (4)	0.0013 (4)	0.0021 (4)
C18	0.0172 (5)	0.0141 (5)	0.0112 (5)	0.0036 (4)	−0.0005 (4)	0.0019 (4)
C19	0.0201 (5)	0.0134 (5)	0.0111 (5)	0.0031 (4)	0.0024 (4)	0.0008 (4)
C20	0.0185 (5)	0.0112 (5)	0.0142 (5)	0.0044 (4)	0.0036 (4)	0.0021 (4)
C21	0.0139 (5)	0.0116 (5)	0.0115 (5)	0.0036 (4)	0.0014 (4)	0.0033 (4)
C22	0.0159 (5)	0.0129 (5)	0.0131 (5)	0.0039 (4)	0.0012 (4)	0.0027 (4)
C23	0.0125 (5)	0.0125 (5)	0.0135 (5)	0.0036 (4)	0.0004 (4)	0.0029 (4)
N3	0.0260 (5)	0.0177 (5)	0.0116 (4)	0.0078 (4)	−0.0019 (4)	−0.0004 (4)
N4	0.0256 (5)	0.0145 (5)	0.0148 (5)	0.0072 (4)	−0.0046 (4)	0.0009 (4)
N5	0.0177 (4)	0.0120 (4)	0.0106 (4)	0.0050 (3)	0.0003 (3)	0.0021 (3)
N6	0.0180 (4)	0.0102 (4)	0.0105 (4)	0.0037 (3)	−0.0004 (3)	0.0006 (3)
N7	0.0170 (4)	0.0101 (4)	0.0109 (4)	0.0047 (3)	0.0008 (3)	0.0004 (3)
C15	0.0152 (5)	0.0099 (4)	0.0120 (5)	0.0017 (4)	0.0019 (4)	0.0013 (4)
C16	0.0145 (5)	0.0111 (4)	0.0116 (5)	0.0029 (4)	0.0022 (4)	0.0024 (4)
O1W	0.0335 (6)	0.0282 (5)	0.0137 (4)	−0.0070 (4)	−0.0010 (4)	0.0062 (4)
O2W	0.0156 (4)	0.0137 (4)	0.0141 (4)	−0.0003 (3)	−0.0010 (3)	0.0031 (3)

Geometric parameters (Å, º) top

Co1—N1	2.0302 (9)	O9—C22	1.2110 (14)
Co1—N2	2.0395 (9)	O10—C22	1.3283 (14)
Co1—O4	2.1363 (8)	O10—H1OA	0.78 (2)
Co1—O1	2.1875 (8)	O11—C23	1.2113 (14)
Co1—O2	2.1967 (8)	O12—C23	1.3242 (13)
Co1—O3	2.2037 (8)	O12—H12B	0.89 (2)
N1—C6	1.3363 (14)	N8—C17	1.3402 (14)
N1—C2	1.3371 (13)	N8—C21	1.3415 (14)
N2—C13	1.3329 (14)	C17—C18	1.3949 (15)
N2—C9	1.3373 (13)	C17—C23	1.5112 (15)
O1—C1	1.2691 (13)	C18—C19	1.3888 (16)
O2—C7	1.2644 (13)	C18—H18A	0.9500
O3—C14	1.2738 (13)	C19—C20	1.3851 (16)
O4—C8	1.2553 (14)	C19—H19A	0.9500
O5—C8	1.2640 (13)	C20—C21	1.3939 (15)
O6—C14	1.2443 (14)	C20—H20A	0.9500
O7—C7	1.2546 (13)	C21—C22	1.4999 (15)
O8—C1	1.2500 (13)	N3—C16	1.3393 (15)
C1—C2	1.5141 (15)	N3—H1N3	0.84 (2)
C2—C3	1.3873 (15)	N3—H2N3	0.86 (2)
C3—C4	1.3920 (15)	N4—C15	1.3271 (15)
C3—H3A	0.9500	N4—H1N4	0.84 (2)
C4—C5	1.3946 (15)	N4—H2N4	0.85 (2)
C4—H4A	0.9500	N5—C16	1.3146 (14)
C5—C6	1.3901 (15)	N5—N6	1.3992 (13)
C5—H5A	0.9500	N6—C15	1.3238 (14)
C6—C7	1.5094 (15)	N6—H1N6	0.876 (19)
C8—C9	1.5081 (15)	N7—C15	1.3553 (14)
C9—C10	1.3882 (15)	N7—C16	1.3765 (14)
C10—C11	1.3950 (16)	N7—H1N7	0.84 (2)
C10—H10A	0.9500	O1W—H1W1	0.78 (2)
C11—C12	1.3962 (15)	O1W—H2W1	0.82 (2)
C11—H11A	0.9500	O2W—H2W2	0.86 (2)
C12—C13	1.3899 (15)	O2W—H1W2	0.98 (3)
C12—H12A	0.9500	O2W—H3W2	0.87 (2)
C13—C14	1.5128 (15)

N1—Co1—N2	165.60 (4)	C12—C11—H11A	120.0
N1—Co1—O4	116.74 (4)	C13—C12—C11	118.22 (10)
N2—Co1—O4	75.79 (3)	C13—C12—H12A	120.9
N1—Co1—O1	76.28 (3)	C11—C12—H12A	120.9
N2—Co1—O1	94.70 (3)	N2—C13—C12	121.33 (10)
O4—Co1—O1	102.06 (3)	N2—C13—C14	113.26 (9)
N1—Co1—O2	75.36 (3)	C12—C13—C14	125.30 (10)
N2—Co1—O2	114.18 (3)	O6—C14—O3	126.51 (10)
O4—Co1—O2	85.99 (3)	O6—C14—C13	118.22 (10)
O1—Co1—O2	151.12 (3)	O3—C14—C13	115.21 (9)
N1—Co1—O3	93.99 (3)	C22—O10—H1OA	110.1 (16)
N2—Co1—O3	74.89 (3)	C23—O12—H12B	113.6 (13)
O4—Co1—O3	148.33 (3)	C17—N8—C21	116.54 (10)
O1—Co1—O3	92.04 (3)	N8—C17—C18	123.48 (10)
O2—Co1—O3	95.24 (3)	N8—C17—C23	116.87 (9)
C6—N1—C2	120.70 (9)	C18—C17—C23	119.64 (10)
C6—N1—Co1	120.21 (7)	C19—C18—C17	118.96 (10)
C2—N1—Co1	118.84 (7)	C19—C18—H18A	120.5
C13—N2—C9	120.81 (9)	C17—C18—H18A	120.5
C13—N2—Co1	119.95 (7)	C20—C19—C18	118.44 (10)
C9—N2—Co1	119.22 (7)	C20—C19—H19A	120.8
C1—O1—Co1	114.51 (7)	C18—C19—H19A	120.8
C7—O2—Co1	115.16 (7)	C19—C20—C21	118.38 (10)
C14—O3—Co1	115.29 (7)	C19—C20—H20A	120.8
C8—O4—Co1	116.54 (7)	C21—C20—H20A	120.8
O8—C1—O1	127.20 (10)	N8—C21—C20	124.19 (10)
O8—C1—C2	116.62 (10)	N8—C21—C22	117.51 (10)
O1—C1—C2	116.17 (9)	C20—C21—C22	118.30 (10)
N1—C2—C3	121.32 (10)	O9—C22—O10	123.98 (11)
N1—C2—C1	113.46 (9)	O9—C22—C21	123.16 (11)
C3—C2—C1	125.22 (10)	O10—C22—C21	112.85 (10)
C2—C3—C4	118.37 (10)	O11—C23—O12	124.81 (10)
C2—C3—H3A	120.8	O11—C23—C17	124.43 (10)
C4—C3—H3A	120.8	O12—C23—C17	110.74 (9)
C3—C4—C5	120.10 (10)	C16—N3—H1N3	119.3 (13)
C3—C4—H4A	120.0	C16—N3—H2N3	117.9 (14)
C5—C4—H4A	120.0	H1N3—N3—H2N3	118.9 (19)
C6—C5—C4	117.77 (10)	C15—N4—H1N4	117.7 (14)
C6—C5—H5A	121.1	C15—N4—H2N4	120.0 (13)
C4—C5—H5A	121.1	H1N4—N4—H2N4	121.8 (19)
N1—C6—C5	121.75 (10)	C16—N5—N6	104.54 (9)
N1—C6—C7	112.49 (9)	C15—N6—N5	110.78 (9)
C5—C6—C7	125.75 (10)	C15—N6—H1N6	128.7 (12)
O7—C7—O2	125.78 (10)	N5—N6—H1N6	120.4 (12)
O7—C7—C6	117.92 (10)	C15—N7—C16	107.23 (9)
O2—C7—C6	116.27 (9)	C15—N7—H1N7	122.3 (13)
O4—C8—O5	126.31 (10)	C16—N7—H1N7	130.4 (13)
O4—C8—C9	116.39 (9)	N6—C15—N4	127.91 (11)
O5—C8—C9	117.30 (10)	N6—C15—N7	106.84 (10)
N2—C9—C10	121.80 (10)	N4—C15—N7	125.25 (10)
N2—C9—C8	111.81 (9)	N5—C16—N3	125.83 (11)
C10—C9—C8	126.33 (10)	N5—C16—N7	110.61 (10)
C9—C10—C11	117.79 (10)	N3—C16—N7	123.53 (10)
C9—C10—H10A	121.1	H1W1—O1W—H2W1	112 (2)
C11—C10—H10A	121.1	H2W2—O2W—H1W2	117 (2)
C10—C11—C12	120.03 (10)	H2W2—O2W—H3W2	107 (2)
C10—C11—H11A	120.0	H1W2—O2W—H3W2	114 (2)

N2—Co1—N1—C6	−129.11 (14)	Co1—O2—C7—O7	173.12 (9)
O4—Co1—N1—C6	81.84 (9)	Co1—O2—C7—C6	−4.72 (12)
O1—Co1—N1—C6	178.61 (9)	N1—C6—C7—O7	−170.09 (10)
O2—Co1—N1—C6	4.12 (8)	C5—C6—C7—O7	8.47 (17)
O3—Co1—N1—C6	−90.27 (8)	N1—C6—C7—O2	7.92 (14)
N2—Co1—N1—C2	45.17 (19)	C5—C6—C7—O2	−173.51 (11)
O4—Co1—N1—C2	−103.88 (8)	Co1—O4—C8—O5	−179.79 (9)
O1—Co1—N1—C2	−7.12 (8)	Co1—O4—C8—C9	1.30 (12)
O2—Co1—N1—C2	178.39 (9)	C13—N2—C9—C10	−0.75 (16)
O3—Co1—N1—C2	84.01 (8)	Co1—N2—C9—C10	177.15 (8)
N1—Co1—N2—C13	30.87 (19)	C13—N2—C9—C8	176.77 (9)
O4—Co1—N2—C13	−177.41 (9)	Co1—N2—C9—C8	−5.33 (12)
O1—Co1—N2—C13	81.32 (8)	O4—C8—C9—N2	2.47 (14)
O2—Co1—N2—C13	−98.53 (8)	O5—C8—C9—N2	−176.54 (10)
O3—Co1—N2—C13	−9.53 (8)	O4—C8—C9—C10	179.86 (10)
N1—Co1—N2—C9	−147.05 (13)	O5—C8—C9—C10	0.85 (16)
O4—Co1—N2—C9	4.67 (8)	N2—C9—C10—C11	−0.58 (16)
O1—Co1—N2—C9	−96.60 (8)	C8—C9—C10—C11	−177.72 (10)
O2—Co1—N2—C9	83.55 (8)	C9—C10—C11—C12	0.86 (16)
O3—Co1—N2—C9	172.55 (9)	C10—C11—C12—C13	0.11 (17)
N1—Co1—O1—C1	7.60 (8)	C9—N2—C13—C12	1.79 (16)
N2—Co1—O1—C1	−161.02 (8)	Co1—N2—C13—C12	−176.09 (8)
O4—Co1—O1—C1	122.53 (8)	C9—N2—C13—C14	−174.64 (9)
O2—Co1—O1—C1	18.69 (12)	Co1—N2—C13—C14	7.48 (12)
O3—Co1—O1—C1	−86.02 (8)	C11—C12—C13—N2	−1.46 (17)
N1—Co1—O2—C7	0.71 (8)	C11—C12—C13—C14	174.52 (10)
N2—Co1—O2—C7	169.25 (8)	Co1—O3—C14—O6	172.81 (10)
O4—Co1—O2—C7	−118.28 (8)	Co1—O3—C14—C13	−10.06 (12)
O1—Co1—O2—C7	−10.43 (12)	N2—C13—C14—O6	179.76 (10)
O3—Co1—O2—C7	93.47 (8)	C12—C13—C14—O6	3.49 (17)
N1—Co1—O3—C14	−160.07 (8)	N2—C13—C14—O3	2.37 (14)
N2—Co1—O3—C14	10.63 (8)	C12—C13—C14—O3	−173.89 (11)
O4—Co1—O3—C14	33.44 (11)	C21—N8—C17—C18	1.17 (16)
O1—Co1—O3—C14	−83.69 (8)	C21—N8—C17—C23	−178.06 (10)
O2—Co1—O3—C14	124.29 (8)	N8—C17—C18—C19	−0.37 (18)
N1—Co1—O4—C8	169.32 (8)	C23—C17—C18—C19	178.84 (10)
N2—Co1—O4—C8	−3.10 (8)	C17—C18—C19—C20	−0.96 (17)
O1—Co1—O4—C8	88.76 (8)	C18—C19—C20—C21	1.41 (17)
O2—Co1—O4—C8	−119.28 (8)	C17—N8—C21—C20	−0.67 (17)
O3—Co1—O4—C8	−25.80 (12)	C17—N8—C21—C22	178.97 (10)
Co1—O1—C1—O8	171.75 (10)	C19—C20—C21—N8	−0.61 (18)
Co1—O1—C1—C2	−6.90 (12)	C19—C20—C21—C22	179.75 (10)
C6—N1—C2—C3	0.73 (16)	N8—C21—C22—O9	179.71 (11)
Co1—N1—C2—C3	−173.52 (8)	C20—C21—C22—O9	−0.62 (18)
C6—N1—C2—C1	−179.91 (9)	N8—C21—C22—O10	−1.23 (15)
Co1—N1—C2—C1	5.85 (12)	C20—C21—C22—O10	178.43 (10)
O8—C1—C2—N1	−177.62 (10)	N8—C17—C23—O11	−8.97 (17)
O1—C1—C2—N1	1.18 (14)	C18—C17—C23—O11	171.78 (12)
O8—C1—C2—C3	1.72 (17)	N8—C17—C23—O12	170.01 (10)
O1—C1—C2—C3	−179.48 (11)	C18—C17—C23—O12	−9.25 (15)
N1—C2—C3—C4	−0.38 (17)	C16—N5—N6—C15	−0.68 (13)
C1—C2—C3—C4	−179.67 (10)	N5—N6—C15—N4	179.92 (12)
C2—C3—C4—C5	−0.34 (17)	N5—N6—C15—N7	0.39 (13)
C3—C4—C5—C6	0.70 (17)	C16—N7—C15—N6	0.05 (13)
C2—N1—C6—C5	−0.35 (16)	C16—N7—C15—N4	−179.50 (11)
Co1—N1—C6—C5	173.82 (8)	N6—N5—C16—N3	178.62 (11)
C2—N1—C6—C7	178.28 (9)	N6—N5—C16—N7	0.70 (12)
Co1—N1—C6—C7	−7.55 (12)	C15—N7—C16—N5	−0.49 (13)
C4—C5—C6—N1	−0.37 (17)	C15—N7—C16—N3	−178.47 (11)
C4—C5—C6—C7	−178.81 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O10ⁱ	0.841 (19)	2.249 (18)	3.0304 (15)	154.5 (17)
N3—H1N3···N8ⁱ	0.841 (19)	2.47 (2)	3.1379 (15)	136.5 (16)
N3—H2N3···O11ⁱ	0.86 (2)	2.28 (2)	2.9563 (15)	135.7 (17)
N4—H1N4···O2	0.85 (2)	2.072 (19)	2.9084 (14)	169 (2)
N4—H2N4···O1W	0.85 (2)	1.96 (2)	2.8057 (16)	172 (2)
N6—H1N6···O3ⁱⁱ	0.877 (18)	1.870 (18)	2.7368 (12)	169.7 (16)
N7—H1N7···O7	0.85 (2)	1.89 (2)	2.7245 (13)	167 (2)
O10—H1OA···O7ⁱ	0.79 (2)	1.86 (2)	2.5775 (13)	152 (3)
O1W—H1W1···O6ⁱⁱⁱ	0.78 (2)	2.06 (2)	2.8315 (14)	172 (2)
O1W—H2W1···O1ⁱⁱ	0.82 (3)	2.23 (3)	2.8901 (14)	138 (2)
O2W—H2W2···O8^iv	0.87 (3)	1.67 (2)	2.5279 (13)	170 (2)
O2W—H1W2···O5^v	0.98 (3)	1.48 (3)	2.4622 (13)	177 (3)
O2W—H3W2···O6ⁱⁱ	0.87 (2)	1.71 (2)	2.5746 (13)	174 (2)
O12—H12B···N5^vi	0.89 (2)	1.76 (2)	2.6303 (14)	169 (2)
C3—H3A···O9^vii	0.95	2.52	3.1725 (14)	126
C5—H5A···O9ⁱ	0.95	2.59	3.5380 (15)	175
C10—H10A···O1^viii	0.95	2.38	3.2669 (14)	156
C19—H19A···O2W	0.95	2.50	3.4269 (15)	165

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

Experimental details

Crystal data
Chemical formula	(C₂H₆N₅)(H₃O)[Co(C₇H₃NO₄)₂]·C₇H₅NO₄·H₂O
M_r	693.42
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.0209 (2), 9.2028 (2), 18.7004 (4)
α, β, γ (°)	98.536 (1), 96.721 (1), 100.515 (1)
V (Å³)	1327.32 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.78 × 0.59 × 0.35

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.595, 0.781
No. of measured, independent and observed [I > 2σ(I)] reflections	25547, 7698, 7360
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.072, 1.05
No. of reflections	7698
No. of parameters	467
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.43

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O10ⁱ	0.841 (19)	2.249 (18)	3.0304 (15)	154.5 (17)
N3—H1N3···N8ⁱ	0.841 (19)	2.47 (2)	3.1379 (15)	136.5 (16)
N3—H2N3···O11ⁱ	0.86 (2)	2.28 (2)	2.9563 (15)	135.7 (17)
N4—H1N4···O2	0.85 (2)	2.072 (19)	2.9084 (14)	169 (2)
N4—H2N4···O1W	0.85 (2)	1.96 (2)	2.8057 (16)	172 (2)
N6—H1N6···O3ⁱⁱ	0.877 (18)	1.870 (18)	2.7368 (12)	169.7 (16)
N7—H1N7···O7	0.85 (2)	1.89 (2)	2.7245 (13)	167 (2)
O10—H1OA···O7ⁱ	0.79 (2)	1.86 (2)	2.5775 (13)	152 (3)
O1W—H1W1···O6ⁱⁱⁱ	0.78 (2)	2.06 (2)	2.8315 (14)	172 (2)
O1W—H2W1···O1ⁱⁱ	0.82 (3)	2.23 (3)	2.8901 (14)	138 (2)
O2W—H2W2···O8^iv	0.87 (3)	1.67 (2)	2.5279 (13)	170 (2)
O2W—H1W2···O5^v	0.98 (3)	1.48 (3)	2.4622 (13)	177 (3)
O2W—H3W2···O6ⁱⁱ	0.87 (2)	1.71 (2)	2.5746 (13)	174 (2)
O12—H12B···N5^vi	0.89 (2)	1.76 (2)	2.6303 (14)	169 (2)
C3—H3A···O9^vii	0.95	2.52	3.1725 (14)	126
C5—H5A···O9ⁱ	0.95	2.59	3.5380 (15)	175
C10—H10A···O1^viii	0.95	2.38	3.2669 (14)	156
C19—H19A···O2W	0.95	2.50	3.4269 (15)	165

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

AJ thanks The Academy of Sciences for the Developing World (TWAS) for the award of a Research and Advanced Training Fellowship, and the H·E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for providing research facilities. SY thanks the School of Physics, Universiti Sains Malaysia, for providing X-ray diffraction research facilities. HKF and MH thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks USM for a post-doctoral research fellowship.

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Volume 67| Part 8| August 2011| Pages m1105-m1106

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,5-Di­amino-4H-1,2,4-triazol-1-ium hydroxonium bis­­(pyridine-2,6-di­carboxyl­ato)cobaltate(II) pyridine-2,6-dicarb­­oxy­lic acid monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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Acknowledgements

References

metal-organic compounds

3,5-Diamino-4H-1,2,4-triazol-1-ium hydroxonium bis(pyridine-2,6-dicarboxylato)cobaltate(II) pyridine-2,6-dicarboxylic acid monohydrate