Hydroxonium hydrate tris­(2,4,6-tri­amino-1,3,5-triazin-1-ium) bis­[bis­(pyri­dine-2,6-dicarboxyl­ato)cuprate(II)] pyridine-2,6-dicarboxylic acid hexa­hydrate

Aghabozorg, H.; Attar Gharamaleki, J.; Olmstead, M.M.; Derikvand, Z.; Hooshmand, S.

doi:10.1107/S1600536809000828

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages m186-m187

doi:10.1107/S1600536809000828

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Hydroxonium hydrate tris(2,4,6-triamino-1,3,5-triazin-1-ium) bis[bis(pyridine-2,6-dicarboxylato)cuprate(II)] pyridine-2,6-dicarboxylic acid hexahydrate

Hossein Aghabozorg,^a Jafar Attar Gharamaleki,^a Marilyn M. Olmstead,^b ^* Zohreh Derikvand ^c and Shabnam Hooshmand ^d

^aFaculty of Chemistry, Tarbiat Moallem University, 49 Mofateh Avenue, Tehran, Iran, ^bDepartment of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA, ^cFaculty of Science, Department of Chemistry, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, and ^dDepartment of Chemistry, Ilam University, Ilam, Iran
^*Correspondence e-mail: olmstead@chem.ucdavis.edu

(Received 5 November 2008; accepted 7 January 2009; online 14 January 2009)

The reaction of copper(II) nitrate hexahydrate with pyridine-2,6-dicarboxylic acid (pydcH₂) and 2,4,6-triamino-1,3,5-triazine (melamine) in aqueous solution in a 1:2:2 molar ratio gave the title compound, (H₅O₂)(C₃H₇N₆)₃[Cu(C₇H₃NO₄)₂]₂·C₇H₅NO₄·6H₂O. The hydroxonium hydrate (H₅O₂)⁺, also known as the Zundel cation, resides on a twofold rotation axis. The O—H distance is 1.274 (14) Å, the O⋯O distance is 2.518 (5) Å, and the O—H—O angle is 162 (8)°. One of the melamine H⁺ cations, the uncoordinated pydcH₂, and two water molecules also reside on crystallographic twofold axes. The Cu^II atom has a tetragonally distorted octahedral coordination environment. The structure features extensive hydrogen bonding, with 21 distinct interactions. There is also a centrosymmetric C=O⋯π interaction with an O⋯centroid distance of 3.288 (3) Å. The structure is similar to a mixed-valence manganese(II/III) structure but shows interesting differences in the metal-atom coordination. One of the water molecules is equally disordered with respect to a twofold axis.

Related literature

For related melamine salts, see: Aghabozorg, Aghajani & Sharif (2006 ); Aghabozorg, Attar Gharamaleki et al. (2008 ); Aghabozorg, Ghadermazi et al. (2008 ); Aghabozorg, Manteghi & Sheshmani (2008 ); Aghabozorg, Zabihi et al. (2006 ); Aghajani et al. (2006 ); Perpétuo & Janczak (2006 ); Sharif et al. (2006 , 2007 ); Zhang & Chen (2005 ). For a nearly isostructural manganese(II/III) structure, see: Aghabozorg, Derikvand et al. (2008 ).

Experimental

Crystal data

(H₅O₂)(C₃H₇N₆)₃[Cu(C₇H₃NO₄)₂]₂·C₇H₅NO₄·6H₂O
M_r = 1481.19
Monoclinic, C 2/c
a = 27.575 (3) Å
b = 22.814 (3) Å
c = 9.8068 (12) Å
β = 108.327 (2)°
V = 5856.5 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.84 mm⁻¹
T = 180 (2) K
0.35 × 0.28 × 0.02 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.758, T_max = 0.983
26801 measured reflections
5309 independent reflections
3805 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.03
5309 reflections
531 parameters
21 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O6	0.87 (3)	1.903 (12)	2.766 (3)	168 (3)
N6—H6A⋯O4ⁱ	0.876 (13)	2.062 (17)	2.880 (4)	155 (3)
N6—H6B⋯O5	0.88 (3)	2.007 (12)	2.872 (3)	167 (3)
N7—H7A⋯N9ⁱⁱ	0.88 (3)	2.086 (11)	2.965 (3)	176 (3)
N7—H7B⋯O9ⁱⁱ	0.879 (12)	2.13 (3)	2.815 (3)	134 (3)
N8—H8B⋯O14	0.88 (3)	1.964 (11)	2.842 (3)	177 (3)
N10—H10A⋯O15	0.882 (12)	1.782 (12)	2.649 (6)	167 (2)
N11—H11A⋯O9ⁱⁱⁱ	0.88 (3)	2.064 (11)	2.939 (3)	172 (3)
N12—H12A⋯N5ⁱⁱ	0.87 (3)	2.090 (12)	2.959 (4)	173 (3)
N12—H12B⋯O1	0.882 (12)	2.07 (2)	2.846 (3)	146 (3)
O10—H10B⋯O13	0.85 (3)	1.83 (3)	2.671 (3)	172 (4)
O11—H11B⋯O2^iv	0.81 (3)	2.10 (3)	2.896 (3)	167 (4)
O12—H12C⋯O8ⁱⁱⁱ	0.84 (3)	1.72 (3)	2.555 (3)	173 (4)
O12—H12D⋯O2	0.84 (3)	1.89 (4)	2.700 (3)	162 (5)
O12—H12E⋯O12^iv	1.274 (14)	1.274 (14)	2.518 (5)	162 (8)
O13—H13A⋯O4^v	0.84 (3)	2.04 (3)	2.870 (3)	172 (4)
O13—H13B⋯N4ⁱⁱ	0.84 (3)	2.066 (17)	2.876 (3)	162 (4)
O14—H14A⋯O6	0.84 (3)	1.831 (12)	2.662 (3)	172 (3)
O14—H14B⋯O3^v	0.84 (3)	2.05 (4)	2.850 (3)	160 (4)
O15—H15A⋯O11^vi	0.84 (3)	1.98 (6)	2.748 (6)	151 (11)
O15—H15B⋯O7ⁱⁱⁱ	0.84 (3)	1.82 (2)	2.636 (5)	163 (7)
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x, y, -z-{\script{1\over 2}}]$ ; (iv) $[-x, y, -z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (vi) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000828/gw2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000828/gw2056Isup2.hkl

checkCIF report

Comment top

We have previously reported a proton-transfer system using pyridine-2,6-dicarboxylic acid (pydcH₂) and 2,4,6-triamino-1,3,5-triazine (melamine, also called tata), (melamineH)₂(pydc) (Sharif et al., 2006). We also reported some complexes of this system (Aghabozorg, Aghajani et al., 2006; Aghajani et al., 2006; Sharif et al. 2007; Aghabozorg, Attar Gharamaleki et al. 2008). In the title compound, melamine is mono-protonated, but it is also known to form (melamineH₂)²⁺ salts with trifluoroacetic acid (Perpétuo & Janczak, 2006), oxalic acid (Zhang et al., 2005), and other strong acids. For more details and related literature see our recent review article (Aghabozorg, Manteghi et al., 2008).

The formula unit of the title compound is depicted in Fig. 1. There are nine different moieties in the asymmetric unit. The cationic portion of the asymmetric unit consists of a half-hydroxonium hydrate, residing on a twofold axis, a molecule of melamineH⁺, and a half- molecule of melamineH⁺ residing on a twofold axis. The anionic portion is the [Cu(pydc)₂]^2– complex ion. In addition, the asymmetric unit contains a half-molecule of neutral pydcH₂ residing on a twofold axis, two full molecules of solvate water, a half-molecule of water on a twofold axis, and another half-molecule of water that is disordered with respect to a twofold axis. In the [Cu(pydc)₂]^2–, the two ligands are almost perpendicular to each other. The dihedral angle between the two pydc planes consisting of the C₇NO₄ set is 89.03 (3)°. The Cu—O and Cu—N distances (Table 1) are in good agreement with those seen in related Cu^II bis(pydc) complexes (Aghabozorg, Zabihi et al., 2006, and Aghabozorg, Ghadermazi et al., 2008 are two examples). Of the four nominally equivalent Cu—O distances, Cu—O5 and Cu—O7 are an average of 0.15 Å longer than the other two, indicating a weak Jahn–Teller distortion and tetragonally distorted octahedral environment. The hydroxonium hydrate (H₅O₂)⁺ cation that resides on a 2-fold rotation axis is bent (details are in Table 2).

A centrosymmetrically related C=O···π interaction between C=O groups and centroids of aromatic rings of pyridine-2,6-dicarboxylate is shown in Fig. 2. With regard to the overall packing, the space between layers of [Cu(pydc)₂]^2– anions is filled with (melamineH)⁺ cations and pydcH₂ molecules (Fig. 3). In fact, the layers involving the Cu^II complex are bridged by (melamineH)⁺ cations via extensive hydrogen bonds (Table 2).

The title compound is related to the recently published structure of (H₅O₂)(melamineH⁺)₃[Mn^II/III(pydc)₂]₂(OH)^.(pydcH₂) ^.5H₂O (Aghabozorg, Derikvand et al., 2008), in which charge balance is achieved by conversion of one of the water molecules to a hydroxide. The Mn—O and Mn—N distances are longer than those of the Cu complex and there is no evidence of Jahn-Teller distortion. There are also differences in the angles about Mn that indicate a distortion away from octahedral towards tetrahedral geometry.

Related literature top

For related melamine salts, see: Aghabozorg, Aghajani & Sharif (2006); Aghabozorg, Attar Gharamaleki et al. (2008); Aghabozorg, Ghadermazi et al. (2008); Aghabozorg, Manteghi & Sheshmani (2008); Aghabozorg, Zabihi et al. (2006); Aghajani et al. (2006); Perpétuo & Janczak (2006); Sharif et al. (2006, 2007); Zhang & Chen (2005). For a nearly isostructural manganese(II/III) structure, see: Aghabozorg, Derikvand et al. (2008).

Experimental top

The title compound was produced by the reaction of Cu(NO₃)₂.6H₂O (145 mg, 0.5 mmol), pyridine-2,6-dicarboxylic acid, pydcH₂, (100 mg, 1 mmol) and 2,4,6-triamino-1,3,5-triazine, (melamine) (110 mg, 1 mmol) in water (50 ml). Blue crystals of the title compound were obtained by the slow evaporation of the solvent at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the constituents of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry codes: (i) -x, y, -1/2 - z, (ii) -x, y, 1/2 - z.
	Fig. 2. Centrosymmetrically related (symmetry code 1/2 - x, 3/2 - y, -z) C=O···π interaction between C=O groups and centroid of the N2/C9—C13) aromatic ring of pyridine-2,6-dicarboxylate. The distances between the O atom and the ring centroid is 3.288 (3) Å.
	Fig. 3. A packing diagram of the title compound. The space between layers of [Cu(pydc)₂]^2– is filled with a layer of (H₅O₂)⁺ and (melamineH)⁺ cations, pydcH₂ and water molecules.

Hydroxonium hydrate tris(2,4,6-triamino-1,3,5-triazin-1-ium) bis[bis(pyridine-2,6-dicarboxylato)cuprate(II)] pyridine-2,6-dicarboxylic acid hexahydrate top

Crystal data top

(H₅O₂)(C₃H₇N₆)₃[Cu(C₇H₃NO₄)₂]₂·C₇H₅NO₄·6H₂O	F(000) = 3048
M_r = 1481.19	D_x = 1.680 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6004 reflections
a = 27.575 (3) Å	θ = 2.8–26.1°
b = 22.814 (3) Å	µ = 0.84 mm⁻¹
c = 9.8068 (12) Å	T = 180 K
β = 108.327 (2)°	Plate, pale blue
V = 5856.5 (13) Å³	0.35 × 0.28 × 0.02 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	5309 independent reflections
Radiation source: fine-focus sealed tube	3805 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 8.3 pixels mm^-1	θ_max = 25.3°, θ_min = 2.8°
ω scans	h = −33→33
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −27→27
T_min = 0.758, T_max = 0.983	l = −11→11
26801 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0411P)² + 8.7866P] where P = (F_o² + 2F_c²)/3
5309 reflections	(Δ/σ)_max = 0.001
531 parameters	Δρ_max = 0.26 e Å⁻³
21 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

(H₅O₂)(C₃H₇N₆)₃[Cu(C₇H₃NO₄)₂]₂·C₇H₅NO₄·6H₂O	V = 5856.5 (13) Å³
M_r = 1481.19	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 27.575 (3) Å	µ = 0.84 mm⁻¹
b = 22.814 (3) Å	T = 180 K
c = 9.8068 (12) Å	0.35 × 0.28 × 0.02 mm
β = 108.327 (2)°

Data collection top

Bruker SMART APEXII diffractometer	5309 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3805 reflections with I > 2σ(I)
T_min = 0.758, T_max = 0.983	R_int = 0.051
26801 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	21 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.26 e Å⁻³
5309 reflections	Δρ_min = −0.77 e Å⁻³
531 parameters

Special details top

Experimental. The crystals cracked when cooled to 90 K so the data was collected at 180 K.

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	Occ. (<1)
Cu1	0.157851 (13)	0.631029 (17)	−0.05095 (3)	0.03071 (12)
O1	0.09962 (8)	0.63287 (9)	0.0509 (2)	0.0352 (5)
O2	0.04357 (8)	0.57153 (9)	0.0993 (2)	0.0396 (5)
O3	0.21154 (8)	0.59453 (9)	−0.1422 (2)	0.0359 (5)
O4	0.24379 (8)	0.50682 (10)	−0.1733 (2)	0.0441 (6)
O5	0.21596 (7)	0.65786 (9)	0.1601 (2)	0.0327 (5)
O6	0.25253 (8)	0.73927 (9)	0.2729 (2)	0.0362 (5)
O7	0.10282 (8)	0.65042 (10)	−0.2763 (2)	0.0374 (5)
O8	0.07941 (8)	0.72696 (9)	−0.4265 (2)	0.0377 (5)
N1	0.14634 (9)	0.54895 (11)	−0.0330 (2)	0.0280 (6)
N2	0.16513 (8)	0.71590 (11)	−0.0740 (2)	0.0291 (6)
C1	0.08130 (11)	0.58215 (13)	0.0608 (3)	0.0295 (7)
C2	0.10898 (10)	0.53146 (13)	0.0179 (3)	0.0279 (6)
C3	0.09751 (11)	0.47292 (14)	0.0232 (3)	0.0336 (7)
H3	0.0712	0.4607	0.0603	0.040*
C4	0.12506 (11)	0.43224 (15)	−0.0267 (3)	0.0377 (7)
H4	0.1177	0.3916	−0.0245	0.045*
C5	0.16359 (11)	0.45086 (15)	−0.0803 (3)	0.0366 (8)
H5	0.1826	0.4233	−0.1156	0.044*
C6	0.17368 (11)	0.50997 (14)	−0.0810 (3)	0.0296 (7)
C7	0.21347 (11)	0.53866 (14)	−0.1368 (3)	0.0327 (7)
C8	0.22339 (10)	0.71221 (14)	0.1673 (3)	0.0296 (7)
C9	0.19487 (10)	0.74812 (14)	0.0362 (3)	0.0287 (7)
C10	0.19848 (11)	0.80844 (14)	0.0269 (3)	0.0341 (7)
H10	0.2197	0.8303	0.1056	0.041*
C11	0.17062 (11)	0.83657 (15)	−0.0989 (3)	0.0364 (7)
H11	0.1724	0.8779	−0.1073	0.044*
C12	0.14016 (11)	0.80339 (14)	−0.2120 (3)	0.0333 (7)
H12	0.1210	0.8216	−0.2993	0.040*
C13	0.13815 (10)	0.74347 (14)	−0.1956 (3)	0.0289 (7)
C14	0.10436 (10)	0.70318 (14)	−0.3083 (3)	0.0301 (7)
N3	0.31880 (9)	0.69464 (11)	0.5251 (2)	0.0276 (5)
H3A	0.3001 (9)	0.7133 (11)	0.449 (2)	0.029 (8)*
N4	0.34173 (9)	0.60470 (11)	0.6466 (2)	0.0279 (5)
N5	0.37566 (9)	0.69628 (11)	0.7606 (2)	0.0283 (5)
N6	0.28551 (9)	0.60781 (12)	0.4159 (2)	0.0308 (6)
H6A	0.2790 (12)	0.5702 (5)	0.415 (3)	0.045 (10)*
H6B	0.2656 (10)	0.6283 (12)	0.344 (2)	0.038 (9)*
N7	0.39782 (10)	0.60852 (12)	0.8748 (3)	0.0348 (6)
H7A	0.4185 (10)	0.6269 (12)	0.950 (2)	0.043 (9)*
H7B	0.3957 (13)	0.5701 (5)	0.877 (4)	0.054 (11)*
N8	0.35019 (10)	0.78255 (12)	0.6365 (3)	0.0324 (6)
H8A	0.3686 (9)	0.8009 (11)	0.714 (2)	0.030 (8)*
H8B	0.3313 (11)	0.8021 (13)	0.561 (2)	0.053 (11)*
C15	0.31528 (10)	0.63496 (13)	0.5310 (3)	0.0273 (6)
C16	0.37112 (10)	0.63705 (13)	0.7578 (3)	0.0273 (6)
C17	0.34873 (10)	0.72446 (13)	0.6423 (3)	0.0270 (6)
N9	0.02898 (8)	0.83461 (10)	−0.1285 (2)	0.0271 (5)
N10	0.0000	0.74606 (16)	−0.2500	0.0301 (8)
H10A	0.0000	0.7074 (5)	−0.2500	0.057 (16)*
N11	0.0000	0.91967 (15)	−0.2500	0.0308 (8)
H11A	−0.0184 (10)	0.9405 (12)	−0.324 (2)	0.040 (9)*
N12	0.05475 (10)	0.74580 (12)	−0.0180 (3)	0.0356 (6)
H12A	0.0731 (10)	0.7644 (12)	0.059 (2)	0.036 (9)*
H12B	0.0558 (13)	0.7072 (5)	−0.020 (4)	0.053 (11)*
C18	0.0000	0.86200 (17)	−0.2500	0.0244 (8)
C19	0.02795 (10)	0.77645 (13)	−0.1311 (3)	0.0277 (6)
O9	0.06509 (9)	0.99585 (10)	−0.0244 (2)	0.0508 (7)
O10	0.09675 (8)	1.07950 (9)	0.0842 (2)	0.0334 (5)
H10B	0.1173 (12)	1.0565 (14)	0.142 (3)	0.075 (14)*
N13	0.0000	1.05523 (15)	−0.2500	0.0279 (8)
C20	0.0000	1.17795 (19)	−0.2500	0.0344 (10)
H20	0.0000	1.2196	−0.2500	0.056 (15)*
C21	0.03105 (11)	1.14704 (13)	−0.1331 (3)	0.0301 (7)
H21	0.0522	1.1670	−0.0509	0.029 (8)*
C22	0.03049 (10)	1.08601 (12)	−0.1391 (3)	0.0256 (6)
C23	0.06522 (11)	1.04884 (14)	−0.0217 (3)	0.0302 (7)
O11	0.0000	0.48788 (15)	0.2500	0.0428 (8)
H11B	−0.0111 (14)	0.5073 (16)	0.302 (4)	0.053 (11)*
O12	−0.01661 (12)	0.66299 (13)	0.1148 (3)	0.0631 (8)
H12C	−0.0356 (13)	0.6839 (16)	0.049 (3)	0.079 (14)*
H12D	0.0013 (16)	0.6374 (16)	0.092 (5)	0.100 (18)*
H12E	0.0000	0.672 (4)	0.2500	0.17 (3)*
O13	0.16865 (9)	1.01368 (11)	0.2655 (2)	0.0372 (5)
H13A	0.1944 (10)	1.0045 (19)	0.242 (4)	0.080 (15)*
H13B	0.1636 (16)	0.9829 (11)	0.306 (4)	0.079 (15)*
O14	0.28646 (9)	0.84247 (11)	0.3914 (2)	0.0411 (6)
H14A	0.2740 (12)	0.8119 (9)	0.347 (3)	0.043 (10)*
H14B	0.2899 (17)	0.8674 (14)	0.333 (4)	0.088 (16)*
O15	−0.0086 (2)	0.6313 (2)	−0.2238 (8)	0.0471 (15)	0.50
H15A	−0.006 (3)	0.599 (2)	−0.261 (12)	0.07 (3)*	0.50
H15B	−0.0385 (11)	0.630 (3)	−0.219 (8)	0.06 (3)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02553 (19)	0.0436 (3)	0.02402 (18)	0.00683 (17)	0.00929 (14)	0.00601 (16)
O1	0.0351 (11)	0.0301 (12)	0.0447 (12)	0.0009 (10)	0.0189 (10)	0.0083 (10)
O2	0.0400 (13)	0.0334 (13)	0.0575 (14)	0.0033 (10)	0.0330 (11)	0.0056 (10)
O3	0.0390 (12)	0.0375 (14)	0.0356 (11)	0.0126 (10)	0.0179 (9)	0.0096 (9)
O4	0.0431 (13)	0.0424 (14)	0.0582 (14)	0.0146 (11)	0.0324 (11)	0.0096 (11)
O5	0.0311 (11)	0.0353 (13)	0.0275 (10)	−0.0019 (10)	0.0033 (9)	0.0064 (9)
O6	0.0333 (12)	0.0361 (13)	0.0323 (11)	0.0008 (10)	0.0006 (9)	0.0084 (9)
O7	0.0388 (12)	0.0390 (14)	0.0386 (12)	0.0103 (10)	0.0181 (10)	0.0129 (10)
O8	0.0362 (12)	0.0424 (14)	0.0292 (11)	0.0005 (10)	0.0030 (9)	0.0125 (9)
N1	0.0244 (12)	0.0386 (15)	0.0204 (11)	0.0077 (11)	0.0062 (10)	0.0031 (10)
N2	0.0188 (12)	0.0456 (16)	0.0245 (12)	0.0075 (11)	0.0090 (10)	0.0114 (11)
C1	0.0289 (16)	0.0325 (18)	0.0296 (15)	0.0026 (13)	0.0131 (13)	0.0048 (13)
C2	0.0241 (14)	0.0347 (18)	0.0239 (14)	0.0027 (13)	0.0060 (12)	0.0008 (12)
C3	0.0230 (15)	0.040 (2)	0.0383 (17)	−0.0007 (14)	0.0097 (13)	−0.0012 (14)
C4	0.0326 (17)	0.0346 (19)	0.0457 (18)	0.0006 (14)	0.0119 (14)	−0.0014 (14)
C5	0.0296 (17)	0.041 (2)	0.0398 (17)	0.0075 (14)	0.0112 (14)	−0.0029 (14)
C6	0.0232 (14)	0.041 (2)	0.0233 (14)	0.0080 (14)	0.0060 (12)	0.0030 (13)
C7	0.0294 (16)	0.042 (2)	0.0271 (15)	0.0100 (15)	0.0087 (13)	0.0077 (13)
C8	0.0203 (14)	0.042 (2)	0.0261 (15)	0.0044 (13)	0.0063 (12)	0.0081 (13)
C9	0.0182 (14)	0.041 (2)	0.0282 (15)	0.0036 (13)	0.0097 (12)	0.0114 (13)
C10	0.0251 (15)	0.042 (2)	0.0348 (16)	0.0002 (14)	0.0091 (13)	0.0080 (14)
C11	0.0296 (16)	0.040 (2)	0.0422 (18)	0.0022 (15)	0.0148 (14)	0.0163 (15)
C12	0.0264 (16)	0.044 (2)	0.0307 (16)	0.0057 (14)	0.0100 (13)	0.0174 (14)
C13	0.0189 (14)	0.044 (2)	0.0267 (14)	0.0051 (13)	0.0109 (12)	0.0123 (13)
C14	0.0217 (14)	0.046 (2)	0.0256 (15)	0.0066 (14)	0.0114 (12)	0.0117 (13)
N3	0.0255 (13)	0.0310 (15)	0.0249 (12)	0.0020 (11)	0.0057 (10)	0.0106 (11)
N4	0.0280 (13)	0.0319 (14)	0.0224 (12)	0.0009 (11)	0.0061 (10)	0.0054 (10)
N5	0.0284 (13)	0.0281 (15)	0.0269 (12)	0.0022 (11)	0.0065 (10)	0.0071 (10)
N6	0.0301 (14)	0.0353 (17)	0.0244 (13)	0.0012 (12)	0.0045 (11)	0.0042 (11)
N7	0.0408 (16)	0.0286 (16)	0.0273 (14)	−0.0003 (13)	−0.0003 (12)	0.0058 (11)
N8	0.0334 (15)	0.0305 (16)	0.0298 (14)	−0.0017 (12)	0.0050 (12)	0.0063 (12)
C15	0.0227 (14)	0.0336 (18)	0.0275 (14)	0.0021 (13)	0.0106 (11)	0.0055 (13)
C16	0.0252 (14)	0.0330 (18)	0.0241 (14)	0.0008 (13)	0.0084 (11)	0.0053 (12)
C17	0.0226 (14)	0.0321 (18)	0.0288 (15)	0.0009 (13)	0.0118 (12)	0.0059 (12)
N9	0.0284 (13)	0.0208 (14)	0.0283 (12)	0.0012 (10)	0.0035 (10)	0.0026 (10)
N10	0.0279 (19)	0.021 (2)	0.038 (2)	0.000	0.0060 (15)	0.000
N11	0.036 (2)	0.021 (2)	0.0269 (19)	0.000	−0.0024 (16)	0.000
N12	0.0334 (15)	0.0259 (17)	0.0409 (16)	0.0012 (12)	0.0024 (12)	0.0097 (13)
C18	0.0213 (19)	0.022 (2)	0.027 (2)	0.000	0.0041 (16)	0.000
C19	0.0234 (14)	0.0267 (18)	0.0336 (16)	0.0009 (12)	0.0097 (12)	0.0025 (12)
O9	0.0626 (16)	0.0264 (14)	0.0390 (13)	−0.0015 (11)	−0.0189 (11)	0.0011 (10)
O10	0.0322 (12)	0.0327 (13)	0.0281 (11)	−0.0022 (10)	−0.0008 (9)	−0.0058 (9)
N13	0.0258 (18)	0.029 (2)	0.0262 (17)	0.000	0.0044 (14)	0.000
C20	0.031 (2)	0.024 (3)	0.046 (3)	0.000	0.010 (2)	0.000
C21	0.0267 (15)	0.0289 (18)	0.0340 (16)	−0.0041 (13)	0.0086 (13)	−0.0063 (12)
C22	0.0241 (15)	0.0244 (17)	0.0271 (14)	−0.0020 (12)	0.0064 (12)	−0.0028 (11)
C23	0.0283 (16)	0.033 (2)	0.0260 (15)	−0.0018 (13)	0.0043 (12)	−0.0054 (12)
O11	0.062 (2)	0.030 (2)	0.042 (2)	0.000	0.0255 (18)	0.000
O12	0.087 (2)	0.069 (2)	0.0308 (14)	0.0485 (17)	0.0157 (14)	0.0130 (13)
O13	0.0320 (13)	0.0404 (15)	0.0374 (12)	0.0012 (11)	0.0086 (10)	0.0076 (10)
O14	0.0568 (15)	0.0361 (15)	0.0267 (12)	−0.0032 (12)	0.0077 (11)	0.0052 (11)
O15	0.032 (4)	0.027 (3)	0.090 (5)	0.000 (2)	0.030 (3)	0.003 (3)

Geometric parameters (Å, º) top

Cu1—N1	1.916 (3)	N5—C16	1.357 (4)
Cu1—N2	1.967 (3)	N6—C15	1.322 (4)
Cu1—O3	2.126 (2)	N6—H6A	0.876 (13)
Cu1—O1	2.142 (2)	N6—H6B	0.88 (3)
Cu1—O5	2.2670 (19)	N7—C16	1.323 (4)
Cu1—O7	2.296 (2)	N7—H7A	0.88 (3)
O1—C1	1.279 (3)	N7—H7B	0.879 (12)
O2—C1	1.237 (3)	N8—C17	1.328 (4)
O3—C7	1.276 (4)	N8—H8A	0.88 (3)
O4—C7	1.242 (3)	N8—H8B	0.88 (3)
O5—C8	1.255 (4)	N9—C19	1.327 (4)
O6—C8	1.256 (3)	N9—C18	1.360 (3)
O7—C14	1.248 (4)	N10—C19	1.367 (3)
O8—C14	1.269 (3)	N10—C19ⁱ	1.367 (3)
N1—C2	1.339 (4)	N10—H10A	0.882 (12)
N1—C6	1.343 (4)	N11—C18	1.315 (5)
N2—C13	1.347 (3)	N11—H11A	0.88 (2)
N2—C9	1.350 (4)	N12—C19	1.323 (4)
C1—C2	1.516 (4)	N12—H12A	0.87 (3)
C2—C3	1.377 (4)	N12—H12B	0.876 (13)
C3—C4	1.383 (4)	C18—N9ⁱ	1.360 (3)
C3—H3	0.9500	O9—C23	1.209 (4)
C4—C5	1.391 (4)	O10—C23	1.325 (3)
C4—H4	0.9500	O10—H10B	0.85 (3)
C5—C6	1.377 (4)	N13—C22	1.345 (3)
C5—H5	0.9500	N13—C22ⁱ	1.345 (3)
C6—C7	1.520 (4)	C20—C21ⁱ	1.388 (4)
C8—C9	1.519 (4)	C20—C21	1.388 (4)
C9—C10	1.385 (4)	C20—H20	0.9500
C10—C11	1.388 (4)	C21—C22	1.393 (4)
C10—H10	0.9500	C21—H21	0.9500
C11—C12	1.387 (4)	C22—C23	1.506 (4)
C11—H11	0.9500	O11—H11B	0.81 (3)
C12—C13	1.379 (4)	O12—H12C	0.84 (3)
C12—H12	0.9500	O12—H12D	0.84 (3)
C13—C14	1.512 (4)	O12—H12E	1.274 (14)
N3—C15	1.367 (4)	O13—H13A	0.84 (3)
N3—C17	1.368 (4)	O13—H13B	0.84 (3)
N3—H3A	0.874 (10)	O14—H14A	0.84 (3)
N4—C15	1.332 (3)	O14—H14B	0.84 (3)
N4—C16	1.355 (4)	O15—H15A	0.84 (3)
N5—C17	1.329 (3)	O15—H15B	0.84 (3)

N1—Cu1—N2	176.51 (9)	N2—C13—C14	113.9 (3)
N1—Cu1—O3	79.24 (9)	C12—C13—C14	123.7 (2)
N2—Cu1—O3	103.15 (9)	O7—C14—O8	126.2 (3)
N1—Cu1—O1	78.83 (9)	O7—C14—C13	117.7 (2)
N2—Cu1—O1	98.79 (9)	O8—C14—C13	116.1 (3)
O3—Cu1—O1	158.06 (8)	C15—N3—C17	119.5 (2)
N1—Cu1—O5	105.67 (8)	C15—N3—H3A	119.4 (19)
N2—Cu1—O5	76.75 (8)	C17—N3—H3A	121.0 (19)
O3—Cu1—O5	95.97 (8)	C15—N4—C16	115.6 (3)
O1—Cu1—O5	89.28 (8)	C17—N5—C16	116.2 (2)
N1—Cu1—O7	101.42 (9)	C15—N6—H6A	123 (2)
N2—Cu1—O7	76.13 (8)	C15—N6—H6B	120 (2)
O3—Cu1—O7	90.42 (7)	H6A—N6—H6B	116 (3)
O1—Cu1—O7	94.57 (7)	C16—N7—H7A	122 (2)
O5—Cu1—O7	152.87 (8)	C16—N7—H7B	120 (2)
C1—O1—Cu1	112.94 (18)	H7A—N7—H7B	119 (3)
C7—O3—Cu1	113.53 (18)	C17—N8—H8A	117 (2)
C8—O5—Cu1	111.97 (16)	C17—N8—H8B	122 (2)
C14—O7—Cu1	111.32 (18)	H8A—N8—H8B	121 (3)
C2—N1—C6	121.0 (3)	N6—C15—N4	120.7 (3)
C2—N1—Cu1	119.6 (2)	N6—C15—N3	117.6 (2)
C6—N1—Cu1	119.2 (2)	N4—C15—N3	121.7 (3)
C13—N2—C9	118.8 (3)	N7—C16—N4	117.3 (3)
C13—N2—Cu1	120.9 (2)	N7—C16—N5	116.8 (3)
C9—N2—Cu1	120.15 (18)	N4—C16—N5	125.9 (2)
O2—C1—O1	126.2 (3)	N8—C17—N5	120.3 (3)
O2—C1—C2	118.7 (3)	N8—C17—N3	118.6 (2)
O1—C1—C2	115.1 (3)	N5—C17—N3	121.1 (3)
N1—C2—C3	121.0 (3)	C19—N9—C18	116.1 (2)
N1—C2—C1	112.9 (3)	C19—N10—C19ⁱ	119.1 (4)
C3—C2—C1	126.0 (3)	C19—N10—H10A	120.47 (18)
C2—C3—C4	118.7 (3)	C19ⁱ—N10—H10A	120.47 (18)
C2—C3—H3	120.7	C18—N11—H11A	123 (2)
C4—C3—H3	120.7	C19—N12—H12A	119 (2)
C3—C4—C5	119.9 (3)	C19—N12—H12B	121 (2)
C3—C4—H4	120.1	H12A—N12—H12B	120 (3)
C5—C4—H4	120.1	N11—C18—N9ⁱ	117.36 (18)
C6—C5—C4	118.7 (3)	N11—C18—N9	117.36 (18)
C6—C5—H5	120.6	N9ⁱ—C18—N9	125.3 (4)
C4—C5—H5	120.6	N12—C19—N9	120.6 (3)
N1—C6—C5	120.7 (3)	N12—C19—N10	117.6 (3)
N1—C6—C7	112.9 (3)	N9—C19—N10	121.7 (3)
C5—C6—C7	126.4 (3)	C23—O10—H10B	110 (3)
O4—C7—O3	126.5 (3)	C22—N13—C22ⁱ	117.0 (3)
O4—C7—C6	118.7 (3)	C21ⁱ—C20—C21	118.9 (4)
O3—C7—C6	114.8 (3)	C21ⁱ—C20—H20	120.5
O5—C8—O6	125.7 (3)	C21—C20—H20	120.5
O5—C8—C9	117.0 (3)	C20—C21—C22	118.5 (3)
O6—C8—C9	117.4 (3)	C20—C21—H21	120.7
N2—C9—C10	121.8 (3)	C22—C21—H21	120.7
N2—C9—C8	114.0 (3)	N13—C22—C21	123.5 (3)
C10—C9—C8	124.3 (3)	N13—C22—C23	114.2 (3)
C9—C10—C11	119.1 (3)	C21—C22—C23	122.3 (2)
C9—C10—H10	120.4	O9—C23—O10	122.8 (3)
C11—C10—H10	120.4	O9—C23—C22	123.3 (2)
C12—C11—C10	119.0 (3)	O10—C23—C22	113.9 (3)
C12—C11—H11	120.5	H12C—O12—H12D	118 (4)
C10—C11—H11	120.5	H12C—O12—H12E	130 (4)
C13—C12—C11	119.0 (3)	H12D—O12—H12E	109 (4)
C13—C12—H12	120.5	H13A—O13—H13B	102 (4)
C11—C12—H12	120.5	H14A—O14—H14B	109 (4)
N2—C13—C12	122.3 (3)	H15A—O15—H15B	102 (3)

Symmetry code: (i) −x, y, −z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O6	0.87 (3)	1.90 (1)	2.766 (3)	168 (3)
N6—H6A···O4ⁱⁱ	0.88 (1)	2.06 (2)	2.880 (4)	155 (3)
N6—H6B···O5	0.88 (3)	2.01 (1)	2.872 (3)	167 (3)
N7—H7A···N9ⁱⁱⁱ	0.88 (3)	2.09 (1)	2.965 (3)	176 (3)
N7—H7B···O9ⁱⁱⁱ	0.88 (1)	2.13 (3)	2.815 (3)	134 (3)
N8—H8B···O14	0.88 (3)	1.96 (1)	2.842 (3)	177 (3)
N10—H10A···O15	0.88 (1)	1.78 (1)	2.649 (6)	167 (2)
N11—H11A···O9ⁱ	0.88 (3)	2.06 (1)	2.939 (3)	172 (3)
N12—H12A···N5ⁱⁱⁱ	0.87 (3)	2.09 (1)	2.959 (4)	173 (3)
N12—H12B···O1	0.88 (1)	2.07 (2)	2.846 (3)	146 (3)
O10—H10B···O13	0.85 (3)	1.83 (3)	2.671 (3)	172 (4)
O11—H11B···O2^iv	0.81 (3)	2.10 (3)	2.896 (3)	167 (4)
O12—H12C···O8ⁱ	0.84 (3)	1.72 (3)	2.555 (3)	173 (4)
O12—H12D···O2	0.84 (3)	1.89 (4)	2.700 (3)	162 (5)
O12—H12E···O12^iv	1.27 (1)	1.27 (1)	2.518 (5)	162 (8)
O13—H13A···O4^v	0.84 (3)	2.04 (3)	2.870 (3)	172 (4)
O13—H13B···N4ⁱⁱⁱ	0.84 (3)	2.07 (2)	2.876 (3)	162 (4)
O14—H14A···O6	0.84 (3)	1.83 (1)	2.662 (3)	172 (3)
O14—H14B···O3^v	0.84 (3)	2.05 (4)	2.850 (3)	160 (4)
O15—H15A···O11^vi	0.84 (3)	1.98 (6)	2.748 (6)	151 (11)
O15—H15B···O7ⁱ	0.84 (3)	1.82 (2)	2.636 (5)	163 (7)

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

Experimental details

Crystal data
Chemical formula	(H₅O₂)(C₃H₇N₆)₃[Cu(C₇H₃NO₄)₂]₂·C₇H₅NO₄·6H₂O
M_r	1481.19
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	180
a, b, c (Å)	27.575 (3), 22.814 (3), 9.8068 (12)
β (°)	108.327 (2)
V (Å³)	5856.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.35 × 0.28 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.758, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	26801, 5309, 3805
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.03
No. of reflections	5309
No. of parameters	531
No. of restraints	21
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.77

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O6	0.87 (3)	1.903 (12)	2.766 (3)	168 (3)
N6—H6A···O4ⁱ	0.876 (13)	2.062 (17)	2.880 (4)	155 (3)
N6—H6B···O5	0.88 (3)	2.007 (12)	2.872 (3)	167 (3)
N7—H7A···N9ⁱⁱ	0.88 (3)	2.086 (11)	2.965 (3)	176 (3)
N7—H7B···O9ⁱⁱ	0.879 (12)	2.13 (3)	2.815 (3)	134 (3)
N8—H8B···O14	0.88 (3)	1.964 (11)	2.842 (3)	177 (3)
N10—H10A···O15	0.882 (12)	1.782 (12)	2.649 (6)	167 (2)
N11—H11A···O9ⁱⁱⁱ	0.88 (3)	2.064 (11)	2.939 (3)	172 (3)
N12—H12A···N5ⁱⁱ	0.87 (3)	2.090 (12)	2.959 (4)	173 (3)
N12—H12B···O1	0.882 (12)	2.07 (2)	2.846 (3)	146 (3)
O10—H10B···O13	0.85 (3)	1.83 (3)	2.671 (3)	172 (4)
O11—H11B···O2^iv	0.81 (3)	2.10 (3)	2.896 (3)	167 (4)
O12—H12C···O8ⁱⁱⁱ	0.84 (3)	1.72 (3)	2.555 (3)	173 (4)
O12—H12D···O2	0.84 (3)	1.89 (4)	2.700 (3)	162 (5)
O12—H12E···O12^iv	1.274 (14)	1.274 (14)	2.518 (5)	162 (8)
O13—H13A···O4^v	0.84 (3)	2.04 (3)	2.870 (3)	172 (4)
O13—H13B···N4ⁱⁱ	0.84 (3)	2.066 (17)	2.876 (3)	162 (4)
O14—H14A···O6	0.84 (3)	1.831 (12)	2.662 (3)	172 (3)
O14—H14B···O3^v	0.84 (3)	2.05 (4)	2.850 (3)	160 (4)
O15—H15A···O11^vi	0.84 (3)	1.98 (6)	2.748 (6)	151 (11)
O15—H15B···O7ⁱⁱⁱ	0.84 (3)	1.82 (2)	2.636 (5)	163 (7)

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

Acknowledgements

The authors thank Tarbiat Moallem University for financial support and the University of California, Davis, for the purchase of the X-ray diffractometer.

References

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Volume 65| Part 2| February 2009| Pages m186-m187

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

Hydroxonium hydrate tris­­(2,4,6-tri­amino-1,3,5-triazin-1-ium) bis­­[bis­­(pyri­dine-2,6-di­carboxyl­ato)cuprate(II)] pyridine-2,6-di­carboxylic acid hexa­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Hydroxonium hydrate tris(2,4,6-triamino-1,3,5-triazin-1-ium) bis[bis(pyridine-2,6-dicarboxylato)cuprate(II)] pyridine-2,6-dicarboxylic acid hexahydrate