(2,2′-Bipyridine)bis­(3-carboxy­pyrazine-2-carboxyl­ato)copper(II) dihydrate

Aghabozorg, H.; Parvizi, M.; Sadrkhanlou, E.

doi:10.1107/S1600536808022885

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1067

doi:10.1107/S1600536808022885

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(2,2′-Bipyridine)bis(3-carboxypyrazine-2-carboxylato)copper(II) dihydrate

Hossein Aghabozorg,^a ^* Mahdieh Parvizi ^b and Elahe Sadrkhanlou ^c

^aDepartment of Chemistry, Tarbiat Moallem University, 49 Mofateh Avenue, Tehran, Iran, ^bDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^cDepartment of Biology, Faculty of Science, Shahed University, Opposite Imam Khomeini's Shrine, Tehran-Qom Highway, Tehran, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 23 June 2008; accepted 21 July 2008; online 26 July 2008)

The title six-coordinated distorted octahedral complex, [Cu(C₆H₃N₂O₄)₂(C₁₀H₈N₂)]·2H₂O, consists of two 3-carboxypyrazine-2-carboxylate anions and one 2,2′-bipyridine ligand. There is a twofold rotation axis positioned at the Cu^II center. The N atoms of the pyrazine ring occupy the axial positions and two proton-transferred O atoms of tbe acid together with the two N atoms of the 2,2′-bipyridine ligand complete the equatorial plane. The interactions existing in the crystal structure are intermolecular O—H⋯O hydrogen bonds, and C—H⋯O and C—O⋯π interactions (O⋯π =3.145 Å, C—O⋯π = 149.75°).

Related literature

There are several compounds made from pyrazine-2,3-dicarboxylic acid, but most of them are in a polymeric form; see, for example: Tombul et al. (2007 , 2008 ). For related literature, see: Egli & Sarkhel (2007 ).

Experimental

Crystal data

[Cu(C₆H₃N₂O₄)₂(C₁₀H₈N₂)]·2H₂O
M_r = 589.96
Monoclinic, C 2/c
a = 18.3080 (8) Å
b = 9.2168 (4) Å
c = 16.3235 (7) Å
β = 122.480 (5)°
V = 2323.59 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 100 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.823, T_max = 0.823
14982 measured reflections
3500 independent reflections
3289 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.063
S = 1.04
3500 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O5ⁱ	0.88	1.66	2.5390 (12)	170
O5—H5A⋯O1	0.84	1.89	2.7218 (13)	173
O5—H5B⋯O4ⁱⁱ	0.86	1.84	2.6989 (13)	177
C7—H7A⋯O2ⁱⁱ	0.95	2.57	3.1144 (14)	117
C8—H8A⋯O2ⁱⁱ	0.95	2.45	3.0433 (13)	121
C9—H9A⋯O5ⁱⁱⁱ	0.95	2.55	3.2168 (13)	127
Symmetry codes: (i) $[x, -y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022885/om2248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022885/om2248Isup2.hkl

checkCIF report

Comment top

The structure consists of [Cu(2,3-pzdcH)₂(2,2'- bpy)]. 2H₂O, where pzdcH₂ and 2,2'-bpy are pyrazine-2,3-dicarboxylic acid and 2,2'-bipyridine, respectively. The presence of bidentate mono anionic (pzdcH)^- and neutral 2,2'-bipyridine ligands results in a neutral complex. The asymmetric unit is given in Fig. 1. The obtained hexacoordinated geometry is distorted octahedral. The bond lengths and angles around the Cu^II center are all in accordance with the geometrical steric effects.

There is a 2-fold rotation axis positioned at Cu^II center, transforming one half of the compound to the other.

The main interaction responsible for stabilizing such a framework is O–H···O hydrogen bonds. The water molecule participates in two hydrogen bonds relating two neighboring complexes. There is also a weaker C–H···O which joins the third complex to the series.

The O3–H3O···O5(x, -y, z - 1/2, 1.664 Å) and O5–H5B···O4 (-x + 3/2, -y + 1/2, -z, 1.839 Å) form hydrogen-bonded chains described by C²₂(14) graph-set descriptor (Fig. 2). Expansion of these chains results in layer. Furthermore, the C–H···O interactions between the complexes themselves help in the stabilization of the layers. In the third dimension, there is a similar layer at about a 4.1 Å distance. These layers are connected to each other via a fascinating C–O···π interaction by C6–O3 and a pyrazine ring (Fig. 3). All factors including O···π distance (3.145 Å), C–O···π angle (α = 149.75°) and dihedral angle between the planes defined by X₂C–O and the aromatic system (ω = 79.18°), are in the mentioned range as in the reference [Egli & Sarkhel, 2007].

Figure 4 represents the packing diagram of this crystal lattice.

Related literature top

There are several compounds made by pyrazine-2,3-dicarboxylic acid, but most of them are in a polymeric form, see, for example: Tombul et al. (2007, 2008). For related literature, see: Egli & Sarkhel (2007).

Experimental top

To a 10 ml of a stirring aqueous solution of pyrazine-2,3-dicarboxylic acid (0.084 g, 0.5 mmol) and 2,2'- bipyridine (0.078 g, 0.5 mmol), was added a 0.5 molar equivalent of CuSO₄. 5 H₂O (0.062 g, 0.25 mmol) at room temperature. A neutral copper(II) complex, [Cu(pzdcH)₂(2,2'- bpy)]. 2H₂O, was isolated as very light blue crystals. Slow evaporation of the solvent result in product complex in a week.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title compound, with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Graph set descriptor of chains made by hydrogen bonding.
	Fig. 3. C–O···π interaction between complexes.
	Fig. 4. Crystal packing of [Cu(pzdcH)₂(2,2'- bpy)]. 2H₂O, along c axis.

(2,2'-Bipyridine)bis(3-carboxypyrazine-2-carboxylato)copper(II) dihydrate top

Crystal data top

[Cu(C₆H₃N₂O₄)₂(C₁₀H₈N₂)]·2H₂O	F(000) = 1204
M_r = 589.96	D_x = 1.686 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9557 reflections
a = 18.3080 (8) Å	θ = 2.6–30.5°
b = 9.2168 (4) Å	µ = 1.01 mm⁻¹
c = 16.3235 (7) Å	T = 100 K
β = 122.480 (5)°	Prism, colourless
V = 2323.59 (18) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	3500 independent reflections
Radiation source: fine-focus sealed tube	3289 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 30.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
T_min = 0.823, T_max = 0.823	k = −13→13
14982 measured reflections	l = −23→23

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)] = 0.023	Hydrogen site location: mixed
wR(F²) = 0.063	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.04P)² + 1.2P] where P = (F_o² + 2F_c²)/3
3500 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Cu(C₆H₃N₂O₄)₂(C₁₀H₈N₂)]·2H₂O	V = 2323.59 (18) Å³
M_r = 589.96	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.3080 (8) Å	µ = 1.01 mm⁻¹
b = 9.2168 (4) Å	T = 100 K
c = 16.3235 (7) Å	0.20 × 0.20 × 0.20 mm
β = 122.480 (5)°

Data collection top

Bruker SMART APEXII diffractometer	3500 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3289 reflections with I > 2σ(I)
T_min = 0.823, T_max = 0.823	R_int = 0.017
14982 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.04	Δρ_max = 0.49 e Å⁻³
3500 reflections	Δρ_min = −0.31 e Å⁻³
177 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
Cu1	1.0000	0.367362 (16)	0.2500	0.01104 (5)
O1	0.91326 (4)	0.21893 (8)	0.16501 (5)	0.01386 (13)
O2	0.85176 (5)	0.08782 (9)	0.02861 (6)	0.02271 (16)
O3	0.90660 (5)	0.00760 (8)	−0.12364 (6)	0.02014 (15)
H3O	0.8658	−0.0282	−0.1804	0.024*
O4	0.81385 (5)	0.19258 (9)	−0.16881 (6)	0.02211 (16)
N1	1.02854 (5)	0.32913 (9)	0.12702 (6)	0.01404 (15)
N2	1.01283 (6)	0.27792 (10)	−0.05007 (6)	0.01888 (17)
N3	0.91587 (5)	0.53313 (8)	0.19274 (6)	0.01230 (14)
C1	0.96492 (6)	0.24626 (10)	0.05929 (7)	0.01255 (15)
C2	0.95681 (6)	0.22146 (10)	−0.02994 (7)	0.01416 (16)
C3	1.07722 (7)	0.35806 (12)	0.01940 (8)	0.01958 (19)
H3A	1.1187	0.3983	0.0079	0.023*
C4	1.08554 (7)	0.38463 (11)	0.10811 (8)	0.01748 (18)
H4A	1.1321	0.4426	0.1556	0.021*
C5	0.90413 (6)	0.17769 (10)	0.08456 (7)	0.01334 (16)
C6	0.88379 (7)	0.13731 (10)	−0.11323 (7)	0.01512 (17)
C7	0.82914 (6)	0.52122 (10)	0.13793 (7)	0.01459 (16)
H7A	0.8039	0.4274	0.1197	0.018*
C8	0.77532 (6)	0.64164 (10)	0.10722 (7)	0.01620 (18)
H8A	0.7142	0.6307	0.0692	0.019*
C9	0.81274 (6)	0.77869 (11)	0.13324 (7)	0.01659 (17)
H9A	0.7773	0.8630	0.1126	0.020*
C10	0.90229 (6)	0.79146 (10)	0.18959 (7)	0.01464 (17)
H10A	0.9289	0.8843	0.2076	0.018*
C11	0.95228 (5)	0.66600 (10)	0.21923 (6)	0.01133 (15)
O5	0.80282 (5)	0.09628 (8)	0.20844 (6)	0.01843 (14)
H5A	0.8335	0.1329	0.1897	0.022*
H5B	0.7644	0.1614	0.1957	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.01075 (8)	0.00986 (8)	0.01153 (8)	0.000	0.00533 (6)	0.000
O1	0.0162 (3)	0.0146 (3)	0.0136 (3)	−0.0032 (2)	0.0099 (3)	−0.0027 (2)
O2	0.0255 (4)	0.0255 (4)	0.0199 (4)	−0.0116 (3)	0.0140 (3)	−0.0098 (3)
O3	0.0209 (3)	0.0171 (3)	0.0184 (3)	0.0053 (3)	0.0079 (3)	−0.0022 (3)
O4	0.0193 (3)	0.0250 (4)	0.0179 (3)	0.0082 (3)	0.0072 (3)	−0.0017 (3)
N1	0.0152 (3)	0.0137 (3)	0.0149 (4)	0.0000 (3)	0.0092 (3)	0.0009 (3)
N2	0.0181 (4)	0.0255 (4)	0.0168 (4)	0.0038 (3)	0.0118 (3)	0.0035 (3)
N3	0.0119 (3)	0.0124 (3)	0.0118 (3)	0.0001 (3)	0.0058 (3)	0.0001 (3)
C1	0.0141 (4)	0.0121 (4)	0.0132 (4)	0.0018 (3)	0.0085 (3)	0.0013 (3)
C2	0.0149 (4)	0.0154 (4)	0.0132 (4)	0.0040 (3)	0.0082 (3)	0.0019 (3)
C3	0.0171 (4)	0.0257 (5)	0.0204 (5)	0.0016 (3)	0.0131 (4)	0.0045 (4)
C4	0.0156 (4)	0.0196 (4)	0.0184 (4)	−0.0010 (3)	0.0099 (4)	0.0018 (3)
C5	0.0146 (4)	0.0134 (4)	0.0133 (4)	−0.0003 (3)	0.0083 (3)	−0.0002 (3)
C6	0.0178 (4)	0.0169 (4)	0.0133 (4)	0.0035 (3)	0.0101 (4)	0.0005 (3)
C7	0.0122 (4)	0.0142 (4)	0.0154 (4)	−0.0007 (3)	0.0060 (3)	−0.0004 (3)
C8	0.0120 (4)	0.0171 (4)	0.0162 (4)	0.0008 (3)	0.0054 (3)	−0.0010 (3)
C9	0.0138 (4)	0.0149 (4)	0.0171 (4)	0.0027 (3)	0.0057 (3)	−0.0008 (3)
C10	0.0144 (4)	0.0122 (4)	0.0153 (4)	0.0006 (3)	0.0067 (3)	−0.0010 (3)
C11	0.0114 (4)	0.0126 (4)	0.0100 (4)	0.0000 (3)	0.0057 (3)	0.0003 (3)
O5	0.0213 (3)	0.0156 (3)	0.0244 (4)	0.0041 (3)	0.0163 (3)	0.0056 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.9880 (7)	C2—C6	1.5117 (14)
Cu1—N3	2.0085 (8)	C3—C4	1.3940 (15)
Cu1—N1	2.3565 (8)	C3—H3A	0.9500
O1—C5	1.2890 (11)	C4—H4A	0.9500
O2—C5	1.2243 (12)	C7—C8	1.3869 (13)
O3—C6	1.3072 (12)	C7—H7A	0.9500
O3—H3O	0.8844	C8—C9	1.3903 (13)
O4—C6	1.2142 (12)	C8—H8A	0.9500
N1—C1	1.3340 (12)	C9—C10	1.3886 (13)
N1—C4	1.3386 (12)	C9—H9A	0.9500
N2—C3	1.3362 (15)	C10—C11	1.3904 (13)
N2—C2	1.3388 (12)	C10—H10A	0.9500
N3—C7	1.3446 (11)	C11—C11ⁱ	1.4754 (17)
N3—C11	1.3496 (12)	O5—H5A	0.8419
C1—C2	1.4012 (13)	O5—H5B	0.8612
C1—C5	1.5169 (12)

O1—Cu1—O1ⁱ	93.03 (4)	C4—C3—H3A	118.9
O1—Cu1—N3ⁱ	166.86 (3)	N1—C4—C3	120.57 (10)
O1—Cu1—N3	94.19 (3)	N1—C4—H4A	119.7
O1ⁱ—Cu1—N3	166.86 (3)	C3—C4—H4A	119.7
N3ⁱ—Cu1—N3	80.95 (4)	O2—C5—O1	125.49 (9)
O1—Cu1—N1ⁱ	91.84 (3)	O2—C5—C1	118.30 (8)
N3—Cu1—N1ⁱ	92.57 (3)	O1—C5—C1	116.20 (8)
O1—Cu1—N1	76.24 (3)	O4—C6—O3	124.67 (10)
N3—Cu1—N1	100.53 (3)	O4—C6—C2	121.68 (9)
N1ⁱ—Cu1—N1	162.80 (4)	O3—C6—C2	113.34 (8)
C5—O1—Cu1	122.13 (6)	N3—C7—C8	122.08 (9)
C6—O3—H3O	109.2	N3—C7—H7A	119.0
C1—N1—C4	118.00 (9)	C8—C7—H7A	119.0
C1—N1—Cu1	107.29 (6)	C7—C8—C9	118.61 (9)
C4—N1—Cu1	134.12 (7)	C7—C8—H8A	120.7
C3—N2—C2	116.72 (9)	C9—C8—H8A	120.7
C7—N3—C11	119.40 (8)	C10—C9—C8	119.48 (9)
C7—N3—Cu1	125.73 (6)	C10—C9—H9A	120.3
C11—N3—Cu1	114.69 (6)	C8—C9—H9A	120.3
N1—C1—C2	120.85 (8)	C9—C10—C11	118.84 (9)
N1—C1—C5	117.05 (8)	C9—C10—H10A	120.6
C2—C1—C5	122.07 (8)	C11—C10—H10A	120.6
N2—C2—C1	121.62 (9)	N3—C11—C10	121.57 (8)
N2—C2—C6	113.75 (8)	N3—C11—C11ⁱ	114.75 (5)
C1—C2—C6	124.57 (8)	C10—C11—C11ⁱ	123.67 (5)
N2—C3—C4	122.22 (9)	H5A—O5—H5B	104.5
N2—C3—H3A	118.9

O1ⁱ—Cu1—O1—C5	−96.65 (7)	C3—N2—C2—C6	177.66 (9)
N3ⁱ—Cu1—O1—C5	26.65 (17)	N1—C1—C2—N2	0.90 (14)
N3—Cu1—O1—C5	94.33 (7)	C5—C1—C2—N2	−177.34 (9)
N1ⁱ—Cu1—O1—C5	−172.96 (7)	N1—C1—C2—C6	−175.91 (9)
N1—Cu1—O1—C5	−5.49 (7)	C5—C1—C2—C6	5.84 (14)
O1—Cu1—N1—C1	8.79 (6)	C2—N2—C3—C4	−1.13 (15)
O1ⁱ—Cu1—N1—C1	101.46 (6)	C1—N1—C4—C3	1.09 (14)
N3ⁱ—Cu1—N1—C1	−164.26 (6)	Cu1—N1—C4—C3	−168.92 (7)
N3—Cu1—N1—C1	−82.99 (6)	N2—C3—C4—N1	0.34 (16)
N1ⁱ—Cu1—N1—C1	55.98 (14)	Cu1—O1—C5—O2	−179.47 (8)
O1—Cu1—N1—C4	179.57 (10)	Cu1—O1—C5—C1	1.41 (11)
O1ⁱ—Cu1—N1—C4	−87.76 (10)	N1—C1—C5—O2	−171.48 (9)
N3ⁱ—Cu1—N1—C4	6.52 (10)	C2—C1—C5—O2	6.83 (14)
N3—Cu1—N1—C4	87.79 (10)	N1—C1—C5—O1	7.71 (12)
N1ⁱ—Cu1—N1—C4	−133.24 (9)	C2—C1—C5—O1	−173.98 (9)
O1—Cu1—N3—C7	15.90 (8)	N2—C2—C6—O4	−96.00 (11)
O1ⁱ—Cu1—N3—C7	−107.29 (14)	C1—C2—C6—O4	81.03 (13)
N3ⁱ—Cu1—N3—C7	−176.39 (10)	N2—C2—C6—O3	77.89 (11)
N1ⁱ—Cu1—N3—C7	−76.14 (8)	C1—C2—C6—O3	−105.07 (11)
N1—Cu1—N3—C7	92.66 (8)	C11—N3—C7—C8	0.14 (14)
O1—Cu1—N3—C11	−169.01 (6)	Cu1—N3—C7—C8	175.02 (7)
O1ⁱ—Cu1—N3—C11	67.81 (15)	N3—C7—C8—C9	0.79 (15)
N3ⁱ—Cu1—N3—C11	−1.30 (5)	C7—C8—C9—C10	−0.57 (15)
N1ⁱ—Cu1—N3—C11	98.96 (6)	C8—C9—C10—C11	−0.53 (15)
N1—Cu1—N3—C11	−92.25 (7)	C7—N3—C11—C10	−1.31 (13)
C4—N1—C1—C2	−1.68 (14)	Cu1—N3—C11—C10	−176.74 (7)
Cu1—N1—C1—C2	170.83 (7)	C7—N3—C11—C11ⁱ	178.90 (9)
C4—N1—C1—C5	176.65 (8)	Cu1—N3—C11—C11ⁱ	3.47 (12)
Cu1—N1—C1—C5	−10.84 (9)	C9—C10—C11—N3	1.50 (14)
C3—N2—C2—C1	0.53 (14)	C9—C10—C11—C11ⁱ	−178.73 (10)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ⁱⁱ	0.88	1.66	2.5390 (12)	170
O5—H5A···O1	0.84	1.89	2.7218 (13)	173
O5—H5B···O4ⁱⁱⁱ	0.86	1.84	2.6989 (13)	177
C7—H7A···O2ⁱⁱⁱ	0.95	2.57	3.1144 (14)	117
C8—H8A···O2ⁱⁱⁱ	0.95	2.45	3.0433 (13)	121
C9—H9A···O5^iv	0.95	2.55	3.2168 (13)	127

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

Experimental details

Crystal data
Chemical formula	[Cu(C₆H₃N₂O₄)₂(C₁₀H₈N₂)]·2H₂O
M_r	589.96
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	18.3080 (8), 9.2168 (4), 16.3235 (7)
β (°)	122.480 (5)
V (Å³)	2323.59 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.823, 0.823
No. of measured, independent and observed [I > 2σ(I)] reflections	14982, 3500, 3289
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.063, 1.04
No. of reflections	3500
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.31

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5ⁱ	0.88	1.66	2.5390 (12)	170
O5—H5A···O1	0.84	1.89	2.7218 (13)	173
O5—H5B···O4ⁱⁱ	0.86	1.84	2.6989 (13)	177
C7—H7A···O2ⁱⁱ	0.95	2.57	3.1144 (14)	117
C8—H8A···O2ⁱⁱ	0.95	2.45	3.0433 (13)	121
C9—H9A···O5ⁱⁱⁱ	0.95	2.55	3.2168 (13)	127

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

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Egli, M. & Sarkhel, S. (2007). Acc. Chem. Res. 40, 197–205. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tombul, M., Güven, K. & Büyükgüngör, O. (2007). Acta Cryst. E63, m1783–m1784. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tombul, M., Güven, K. & Svoboda, I. (2008). Acta Cryst. E64, m246–m247. Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1067

doi:10.1107/S1600536808022885

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