Bis(8-hy­droxy-2-methyl­quinolinium) bis­(pyridine-2,6-dicarboxyl­ato)cuprate(II) methanol monosolvate monohydrate

Aghabozorg, H.; Gholizadeh, A.; Mirzaei, M.; Notash, B.

doi:10.1107/S160053681100674X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages m379-m380

doi:10.1107/S160053681100674X

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Bis(8-hydroxy-2-methylquinolinium) bis(pyridine-2,6-dicarboxylato)cuprate(II) methanol monosolvate monohydrate

Hossein Aghabozorg,^a Ahmad Gholizadeh,^a ^* Masoud Mirzaei ^b and Behrouz Notash ^c

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad 917791436, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: r3.chemist@gmail.com

(Received 5 February 2011; accepted 22 February 2011; online 26 February 2011)

The title compound, (C₁₀H₁₀NO)₂[Cu(C₇H₃NO₄)₂]·CH₃OH·H₂O was prepared by the reaction of copper(II) nitrate hexahydrate, 8-hydroxy-2-methylquinoline, and pyridine-2,6-dicarboxylic acid in a 1:2:2 molar ratio in an aqueous solution. The geometry of the resulting CuN₂O₄ coordination can be described as distorted octahedral. In the crystal, there are several intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. An intramolecular N—H⋯O hydrogen bond occurs in one of the cations. Considerable π–π stacking interactions are also observed between the aromatic rings of the cations, with centroid–centroid distances of 3.4567 (13), 3.5342 (14), 3.6941 (14) and 3.4568 (13) Å. These non-covalent interactions connect the components, forming a three-dimensional supramolecular structure.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ). For examples of proton transfer from pyridine-2,6-dicarboxylic acid (pydcH₂) to different amine base ligands, see: Eshtiagh-Hosseini et al. (2010a ,b ,c).

Experimental

Crystal data

(C₁₀H₁₀NO)₂[Cu(C₇H₃NO₄)₂]·CH₄O·H₂O
M_r = 764.20
Triclinic, $[P \overline 1]$
a = 10.116 (2) Å
b = 12.895 (3) Å
c = 14.816 (3) Å
α = 64.45 (3)°
β = 76.23 (3)°
γ = 83.74 (3)°
V = 1693.5 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 298 K
0.5 × 0.4 × 0.3 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.714, T_max = 0.803
18924 measured reflections
9061 independent reflections
7185 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.01
9061 reflections
498 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O9	0.83 (3)	2.37 (2)	2.692 (2)	104.3 (17)
N3—H3A⋯O11	0.83 (3)	1.93 (3)	2.739 (3)	164 (2)
N4—H4A⋯O8ⁱ	0.95 (3)	1.87 (3)	2.723 (2)	149 (2)
O9—H9A⋯O5	0.78 (3)	1.79 (3)	2.563 (2)	176 (3)
O10—H10A⋯O4	0.87 (4)	1.70 (4)	2.555 (3)	167 (3)
O11—H11A⋯O1ⁱ	0.83 (4)	1.88 (4)	2.706 (3)	172 (4)
O12—H12A⋯O7	0.82 (3)	2.14 (3)	2.895 (3)	154 (4)
O12—H12B⋯O2ⁱⁱ	0.82 (4)	2.21 (4)	2.974 (3)	156 (4)
C10—H10⋯O3ⁱⁱⁱ	0.93	2.55	3.177 (3)	125
C15—H15C⋯O2ⁱ	0.96	2.55	3.480 (3)	163
C17—H17⋯O6^iv	0.93	2.29	3.185 (3)	161
C25—H25C⋯O8ⁱ	0.96	2.48	3.212 (3)	133
C27—H27⋯O2^v	0.93	2.50	3.394 (3)	162
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+1, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z+1; (v) x-1, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100674X/vm2078sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100674X/vm2078Isup2.hkl

checkCIF report

Comment top

Our research focusses on water soluble proton transfer compounds as novel self-assembled systems that can function as suitable ligands in the synthesis of metal complexes. In this regard, we have reported examples of proton transfer from pyridine-2,6-dicarboxylic acid (pydcH₂) to different amine base ligands (Eshtiagh-Hosseini et al. 2010a,b,c). This has resulted in the formation of some novel proton transfer compounds based on carboxylic acid ligand derivatives (Aghabozorg et al. 2008).

The molecular structure of the title compound is presented in Fig. 1. In the title compound, Cu^II ion is six-coordinated by two pyridine-2,6-dicarboxylate, or (pydc)^2- groups and each (pydc)^2- ligand is coordinating through one pyridine N atom and two carboxylate O atoms. The atoms N1 and N2 of the two (pydc)^2- fragments occupy the axial positions, while atoms O1, O3, O5, and O7 form the equatorial plane [with Cu—O distances ranging from 2.1799 (16) to 2.2070 (16) Å]. The N1—Cu1—N2 angle [174.84 (5)°] deviates little from linearity. The O3—Cu1—O7 and O1—Cu1—O5 bond angles are equal to 91.22 (6)° and 94.25 (6)°, respectively. So the geometry of the resulting CuN2O4 coordination can be described as distorted octahedral. The packing diagram of the title compound is shown in Fig. 2. It is interesting to note that the space between the layers of [Cu(pydc)₂]^2- units is occupied by (8hmqH)⁺ cations and uncoordinated water and methanol molecules, which the latter bridge the anionic and cationic units via hydrogen bonds (Fig 2 and Table 1). In the crystal structure, there are several intermolecular O—H···O, N—H···O, C—H···O and intramolecular N—H···O hydrogen bonds (Fig 2 and Table 1).

There are also extensive π–π interactions (Fig. 3) between the rings of (8hmqH)⁺ fragments with centroid–centroid distances for Cg7—Cg10^vi, Cg10—Cg11^vii, Cg7—Cg7^iv and Cg10—Cg7^viii equal to 3.4567 (13), 3.5342 (14), 3.6941 (14) and 3.4568 (13) Å, respectively, where Cg7, Cg10 and Cg11 are the centroids of N3/C16—C19/C24, N4/C26—C29/C34 and C29—C34, respectively (symmetry codes: iv: 1 - x,2 - y,1 - z; vi: x,1 + y,z; vii:1 - x,-y,2 - z; viii: x,-1 + y,z).

In the crystal packing a wide range of non-covalent interactions, consisting of hydrogen bonding and π ···π interactions plays an important role in the stabilization of the three-dimensional supramolecular network.

Related literature top

For background to proton-transfer compounds, see: Aghabozorg et al. (2008). For examples of proton transfer from pyridine-2,6-dicarboxylic acid (pydcH₂) to different amine base ligands, see: Eshtiagh-Hosseini et al. (2010a,b,c).

Experimental top

A solution of 8-hydroxy-2-methylquinoline (0.320 g, 2 mmol) in methanol (10 ml) and 2,6-pyridine dicarboxylic acid (0.170 g, 1 mmol) in methanol (10 ml) were mixed and stirrered until a clear solution was obtained. A solution of Cu(NO₃)₂.3H₂0 (0.121 g, 0.5 mmol) in methanol (5 ml) was added to the acid-base mixture and stirred for 30 min. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation after two weeks.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The packing diagram of the title compound. The intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds are shown as green dashed lines.
	Fig. 3. The packing diagram of the title compound showing π-π interactions between (8hmqH)⁺ fragments. Only (8hmqH)⁺ fragments without hydrogen atoms are shown for clarity. Cg7, Cg10 and Cg11 are the centroids of rings N3/C16—C19/C24, N4/C26—C29/C34 and C29—C34, respectively (symmetry codes: iv: 1 - x,2 - y,1 - z; vi: x,1 + y,z; vii:1 - x,-y,2 - z; viii: x,-1 + y,z).

Bis(8-hydroxy-2-methylquinolinium) bis(pyridine-2,6-dicarboxylato)cuprate(II) methanol monosolvate monohydrate top

Crystal data top

(C₁₀H₁₀NO)₂[Cu(C₇H₃NO₄)₂]·CH₄O·H₂O	Z = 2
M_r = 764.20	F(000) = 790
Triclinic, P1	D_x = 1.499 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.116 (2) Å	Cell parameters from 9061 reflections
b = 12.895 (3) Å	θ = 2.3–29.2°
c = 14.816 (3) Å	µ = 0.72 mm⁻¹
α = 64.45 (3)°	T = 298 K
β = 76.23 (3)°	Block, green
γ = 83.74 (3)°	0.5 × 0.4 × 0.3 mm
V = 1693.5 (8) Å³

Data collection top

Stoe IPDS II diffractometer	9061 independent reflections
Radiation source: fine-focus sealed tube	7185 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 2.3°
rotation method scans	h = −13→13
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	k = −17→17
T_min = 0.714, T_max = 0.803	l = −20→18
18924 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0728P)²] where P = (F_o² + 2F_c²)/3
9061 reflections	(Δ/σ)_max = 0.002
498 parameters	Δρ_max = 0.70 e Å⁻³
2 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)₂[Cu(C₇H₃NO₄)₂]·CH₄O·H₂O	γ = 83.74 (3)°
M_r = 764.20	V = 1693.5 (8) Å³
Triclinic, P1	Z = 2
a = 10.116 (2) Å	Mo Kα radiation
b = 12.895 (3) Å	µ = 0.72 mm⁻¹
c = 14.816 (3) Å	T = 298 K
α = 64.45 (3)°	0.5 × 0.4 × 0.3 mm
β = 76.23 (3)°

Data collection top

Stoe IPDS II diffractometer	9061 independent reflections
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005)	7185 reflections with I > 2σ(I)
T_min = 0.714, T_max = 0.803	R_int = 0.028
18924 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	2 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.70 e Å⁻³
9061 reflections	Δρ_min = −0.45 e Å⁻³
498 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	0.987953 (19)	0.531740 (17)	0.743974 (16)	0.03101 (7)
N1	0.88383 (13)	0.54422 (11)	0.86756 (11)	0.0300 (3)
N2	1.09007 (13)	0.53417 (11)	0.61416 (10)	0.0279 (3)
O5	0.89361 (13)	0.67395 (12)	0.63268 (11)	0.0447 (3)
O3	0.81065 (14)	0.42206 (13)	0.78562 (11)	0.0460 (3)
O1	1.11637 (13)	0.64363 (13)	0.76480 (11)	0.0440 (3)
O7	1.12019 (15)	0.38075 (12)	0.79369 (10)	0.0450 (3)
O8	1.28336 (16)	0.28824 (13)	0.72425 (12)	0.0545 (4)
O2	1.11205 (17)	0.73177 (15)	0.86636 (13)	0.0587 (4)
O4	0.61123 (14)	0.37723 (14)	0.89804 (13)	0.0536 (4)
C1	0.92907 (16)	0.61020 (14)	0.90270 (13)	0.0317 (3)
C5	0.76455 (16)	0.48968 (14)	0.91421 (13)	0.0331 (3)
C7	0.72560 (18)	0.42323 (15)	0.86147 (14)	0.0371 (4)
C6	1.06461 (17)	0.66757 (15)	0.84037 (14)	0.0368 (4)
C8	1.06465 (16)	0.61551 (13)	0.52592 (13)	0.0305 (3)
C14	1.19898 (18)	0.36591 (15)	0.72033 (14)	0.0351 (3)
C2	0.8541 (2)	0.62252 (17)	0.98891 (15)	0.0420 (4)
H2	0.8858	0.6685	1.0132	0.050*
C12	1.18579 (16)	0.45418 (14)	0.61431 (13)	0.0313 (3)
O9	0.66369 (14)	0.76955 (12)	0.66892 (13)	0.0495 (4)
O6	0.92311 (15)	0.77708 (13)	0.46303 (12)	0.0573 (4)
C9	1.13573 (19)	0.61976 (16)	0.43302 (14)	0.0400 (4)
H9	1.1166	0.6763	0.3723	0.048*
C10	1.2365 (2)	0.53816 (19)	0.43151 (15)	0.0481 (5)
H10	1.2865	0.5394	0.3696	0.058*
N3	0.45289 (14)	0.91753 (13)	0.63308 (11)	0.0325 (3)
C23	0.68490 (17)	0.87638 (16)	0.65494 (15)	0.0375 (4)
C24	0.57362 (16)	0.95441 (15)	0.63553 (13)	0.0325 (3)
C11	1.2618 (2)	0.45481 (18)	0.52344 (15)	0.0452 (4)
H11	1.3295	0.3998	0.5239	0.054*
C16	0.34540 (17)	0.98636 (16)	0.61397 (13)	0.0372 (4)
C3	0.7318 (2)	0.5658 (2)	1.03830 (16)	0.0487 (5)
H3	0.6807	0.5730	1.0965	0.058*
C15	0.21709 (19)	0.9375 (2)	0.61694 (17)	0.0477 (5)
H15A	0.2375	0.8892	0.5809	0.072*
H15B	0.1575	0.9988	0.5850	0.072*
H15C	0.1735	0.8929	0.6868	0.072*
C4	0.68596 (19)	0.49856 (19)	1.00097 (15)	0.0452 (4)
H4	0.6038	0.4598	1.0334	0.054*
O10	0.52372 (17)	0.25204 (13)	0.83028 (15)	0.0587 (4)
N4	0.38002 (15)	0.08098 (13)	0.84401 (12)	0.0349 (3)
C21	0.8161 (2)	1.0311 (2)	0.64068 (19)	0.0548 (5)
H21	0.8979	1.0560	0.6426	0.066*
C26	0.30049 (18)	0.00004 (17)	0.85244 (14)	0.0400 (4)
C19	0.58640 (19)	1.06926 (16)	0.61857 (14)	0.0389 (4)
C33	0.58524 (19)	0.14932 (17)	0.85447 (16)	0.0415 (4)
C25	0.1594 (2)	0.0336 (2)	0.83583 (19)	0.0551 (5)
H25A	0.1027	0.0378	0.8961	0.083*
H25B	0.1237	−0.0227	0.8219	0.083*
H25C	0.1609	0.1072	0.7787	0.083*
C17	0.3561 (2)	1.10237 (18)	0.59373 (15)	0.0460 (5)
H17	0.2828	1.1521	0.5778	0.055*
C22	0.80401 (19)	0.9164 (2)	0.65722 (18)	0.0490 (5)
H22	0.8780	0.8667	0.6700	0.059*
C34	0.50978 (17)	0.05901 (15)	0.86173 (13)	0.0337 (3)
C18	0.4726 (2)	1.14235 (17)	0.59722 (16)	0.0475 (5)
H18	0.4775	1.2189	0.5854	0.057*
C20	0.7101 (2)	1.10638 (19)	0.62198 (18)	0.0508 (5)
H20	0.7194	1.1819	0.6115	0.061*
C32	0.7142 (2)	0.1243 (2)	0.87438 (17)	0.0510 (5)
H32	0.7665	0.1821	0.8698	0.061*
C29	0.56299 (19)	−0.05345 (16)	0.88863 (14)	0.0399 (4)
C27	0.3516 (2)	−0.11168 (18)	0.87752 (16)	0.0474 (5)
H27	0.2976	−0.1686	0.8825	0.057*
C28	0.4794 (2)	−0.13769 (17)	0.89464 (16)	0.0478 (5)
H28	0.5124	−0.2123	0.9106	0.057*
C31	0.7666 (2)	0.0131 (2)	0.90131 (18)	0.0567 (6)
H31	0.8536	−0.0018	0.9148	0.068*
C30	0.6951 (2)	−0.0749 (2)	0.90864 (18)	0.0537 (5)
H30	0.7330	−0.1482	0.9266	0.064*
C13	0.95099 (17)	0.69800 (15)	0.53946 (15)	0.0371 (4)
O11	0.37869 (17)	0.70218 (16)	0.6708 (2)	0.0806 (7)
C35	0.4497 (3)	0.6032 (2)	0.6755 (3)	0.0786 (9)
H35A	0.5415	0.6223	0.6374	0.118*
H35B	0.4066	0.5655	0.6467	0.118*
H35C	0.4505	0.5528	0.7456	0.118*
O12	0.9690 (3)	0.1914 (2)	0.96545 (19)	0.0947 (8)
H3A	0.446 (2)	0.8493 (19)	0.6449 (16)	0.035 (5)*
H4A	0.342 (2)	0.156 (2)	0.8246 (19)	0.054 (7)*
H9A	0.732 (3)	0.738 (3)	0.660 (2)	0.070 (9)*
H10A	0.564 (3)	0.296 (3)	0.846 (2)	0.075 (9)*
H11A	0.298 (4)	0.689 (3)	0.702 (3)	0.094 (11)*
H12A	1.029 (3)	0.227 (3)	0.917 (2)	0.113*
H12B	0.927 (4)	0.221 (3)	1.003 (3)	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02831 (10)	0.03006 (11)	0.03525 (12)	0.00009 (7)	−0.00293 (7)	−0.01629 (8)
N1	0.0281 (6)	0.0299 (6)	0.0327 (7)	−0.0011 (5)	−0.0045 (5)	−0.0146 (6)
N2	0.0274 (6)	0.0269 (6)	0.0296 (7)	0.0023 (5)	−0.0063 (5)	−0.0126 (5)
O5	0.0377 (6)	0.0417 (7)	0.0478 (8)	0.0125 (5)	−0.0056 (6)	−0.0172 (6)
O3	0.0490 (7)	0.0507 (8)	0.0423 (8)	−0.0129 (6)	0.0001 (6)	−0.0253 (6)
O1	0.0337 (6)	0.0550 (8)	0.0484 (8)	−0.0097 (5)	0.0033 (5)	−0.0304 (7)
O7	0.0557 (8)	0.0449 (7)	0.0320 (7)	0.0042 (6)	−0.0071 (6)	−0.0161 (6)
O8	0.0634 (9)	0.0454 (8)	0.0517 (9)	0.0267 (7)	−0.0230 (7)	−0.0183 (7)
O2	0.0605 (9)	0.0664 (10)	0.0627 (10)	−0.0269 (8)	−0.0034 (7)	−0.0386 (8)
O4	0.0424 (7)	0.0590 (9)	0.0635 (10)	−0.0217 (6)	0.0021 (7)	−0.0316 (8)
C1	0.0317 (7)	0.0315 (8)	0.0344 (8)	0.0016 (6)	−0.0082 (6)	−0.0160 (7)
C5	0.0301 (7)	0.0335 (8)	0.0335 (8)	−0.0038 (6)	−0.0032 (6)	−0.0130 (7)
C7	0.0377 (8)	0.0354 (9)	0.0378 (9)	−0.0072 (7)	−0.0048 (7)	−0.0149 (7)
C6	0.0349 (8)	0.0376 (9)	0.0413 (10)	−0.0057 (7)	−0.0065 (7)	−0.0194 (8)
C8	0.0291 (7)	0.0269 (7)	0.0348 (8)	0.0005 (6)	−0.0098 (6)	−0.0108 (6)
C14	0.0390 (8)	0.0329 (8)	0.0356 (9)	0.0057 (6)	−0.0129 (7)	−0.0153 (7)
C2	0.0466 (10)	0.0473 (10)	0.0410 (10)	0.0029 (8)	−0.0099 (8)	−0.0273 (9)
C12	0.0329 (7)	0.0307 (8)	0.0335 (8)	0.0061 (6)	−0.0093 (6)	−0.0167 (7)
O9	0.0309 (6)	0.0377 (7)	0.0792 (11)	0.0076 (5)	−0.0099 (7)	−0.0266 (7)
O6	0.0513 (8)	0.0447 (8)	0.0548 (9)	0.0159 (6)	−0.0168 (7)	−0.0022 (7)
C9	0.0460 (9)	0.0398 (9)	0.0307 (9)	0.0008 (7)	−0.0107 (7)	−0.0105 (7)
C10	0.0538 (11)	0.0567 (12)	0.0327 (9)	0.0082 (9)	−0.0030 (8)	−0.0229 (9)
N3	0.0306 (7)	0.0334 (7)	0.0327 (7)	0.0039 (5)	−0.0044 (5)	−0.0153 (6)
C23	0.0317 (8)	0.0381 (9)	0.0422 (10)	0.0035 (7)	−0.0053 (7)	−0.0186 (8)
C24	0.0308 (7)	0.0367 (8)	0.0302 (8)	0.0021 (6)	−0.0037 (6)	−0.0162 (7)
C11	0.0467 (10)	0.0489 (11)	0.0414 (10)	0.0176 (8)	−0.0082 (8)	−0.0249 (9)
C16	0.0310 (8)	0.0473 (10)	0.0292 (8)	0.0087 (7)	−0.0048 (6)	−0.0151 (7)
C3	0.0452 (10)	0.0655 (13)	0.0383 (10)	0.0003 (9)	0.0021 (8)	−0.0302 (10)
C15	0.0321 (8)	0.0600 (12)	0.0479 (11)	0.0052 (8)	−0.0096 (8)	−0.0207 (10)
C4	0.0350 (9)	0.0570 (12)	0.0390 (10)	−0.0082 (8)	0.0031 (7)	−0.0197 (9)
O10	0.0600 (9)	0.0412 (8)	0.0869 (13)	−0.0020 (7)	−0.0339 (9)	−0.0282 (8)
N4	0.0353 (7)	0.0378 (8)	0.0338 (8)	−0.0020 (6)	−0.0096 (6)	−0.0155 (6)
C21	0.0419 (10)	0.0660 (14)	0.0639 (14)	−0.0103 (9)	−0.0095 (9)	−0.0328 (12)
C26	0.0380 (9)	0.0491 (10)	0.0346 (9)	−0.0105 (7)	−0.0024 (7)	−0.0195 (8)
C19	0.0434 (9)	0.0373 (9)	0.0353 (9)	0.0007 (7)	−0.0040 (7)	−0.0171 (7)
C33	0.0429 (9)	0.0444 (10)	0.0429 (10)	−0.0047 (8)	−0.0140 (8)	−0.0201 (8)
C25	0.0367 (10)	0.0753 (15)	0.0601 (14)	−0.0075 (9)	−0.0082 (9)	−0.0341 (12)
C17	0.0470 (10)	0.0436 (10)	0.0400 (10)	0.0173 (8)	−0.0110 (8)	−0.0139 (8)
C22	0.0334 (9)	0.0571 (12)	0.0597 (13)	0.0040 (8)	−0.0121 (8)	−0.0275 (10)
C34	0.0360 (8)	0.0367 (8)	0.0297 (8)	−0.0025 (6)	−0.0090 (6)	−0.0136 (7)
C18	0.0566 (12)	0.0333 (9)	0.0472 (11)	0.0059 (8)	−0.0067 (9)	−0.0155 (8)
C20	0.0561 (12)	0.0436 (11)	0.0563 (13)	−0.0106 (9)	−0.0070 (10)	−0.0246 (10)
C32	0.0411 (10)	0.0705 (14)	0.0522 (12)	−0.0073 (9)	−0.0134 (9)	−0.0323 (11)
C29	0.0444 (9)	0.0401 (9)	0.0322 (9)	0.0020 (7)	−0.0087 (7)	−0.0128 (7)
C27	0.0549 (11)	0.0419 (10)	0.0439 (11)	−0.0167 (8)	−0.0006 (9)	−0.0181 (9)
C28	0.0617 (12)	0.0349 (9)	0.0419 (11)	−0.0013 (8)	−0.0065 (9)	−0.0138 (8)
C31	0.0369 (10)	0.0833 (17)	0.0556 (13)	0.0081 (10)	−0.0177 (9)	−0.0323 (12)
C30	0.0521 (11)	0.0576 (13)	0.0495 (12)	0.0180 (10)	−0.0198 (10)	−0.0203 (10)
C13	0.0302 (8)	0.0301 (8)	0.0455 (10)	0.0033 (6)	−0.0095 (7)	−0.0107 (7)
O11	0.0351 (8)	0.0562 (10)	0.139 (2)	−0.0101 (7)	0.0123 (10)	−0.0444 (12)
C35	0.0630 (15)	0.0560 (15)	0.107 (2)	−0.0065 (12)	0.0113 (15)	−0.0386 (16)
O12	0.125 (2)	0.0851 (16)	0.0707 (15)	−0.0470 (14)	0.0092 (13)	−0.0350 (12)

Geometric parameters (Å, º) top

Cu1—N2	1.9433 (15)	C15—H15A	0.9600
Cu1—N1	1.9461 (15)	C15—H15B	0.9600
Cu1—O5	2.1799 (16)	C15—H15C	0.9600
Cu1—O7	2.1880 (16)	C4—H4	0.9300
Cu1—O1	2.2018 (14)	O10—C33	1.337 (3)
Cu1—O3	2.2070 (16)	O10—H10A	0.87 (3)
N1—C1	1.336 (2)	N4—C26	1.332 (2)
N1—C5	1.341 (2)	N4—C34	1.375 (2)
N2—C12	1.335 (2)	N4—H4A	0.95 (3)
N2—C8	1.339 (2)	C21—C20	1.360 (3)
O5—C13	1.276 (2)	C21—C22	1.405 (3)
O3—C7	1.247 (2)	C21—H21	0.9300
O1—C6	1.268 (2)	C26—C27	1.396 (3)
O7—C14	1.260 (2)	C26—C25	1.492 (3)
O8—C14	1.234 (2)	C19—C20	1.407 (3)
O2—C6	1.230 (2)	C19—C18	1.412 (3)
O4—C7	1.248 (2)	C33—C32	1.379 (3)
C1—C2	1.386 (3)	C33—C34	1.413 (3)
C1—C6	1.520 (2)	C25—H25A	0.9600
C5—C4	1.385 (3)	C25—H25B	0.9600
C5—C7	1.516 (2)	C25—H25C	0.9600
C8—C9	1.374 (3)	C17—C18	1.357 (3)
C8—C13	1.517 (2)	C17—H17	0.9300
C14—C12	1.518 (2)	C22—H22	0.9300
C2—C3	1.380 (3)	C34—C29	1.409 (3)
C2—H2	0.9300	C18—H18	0.9300
C12—C11	1.380 (3)	C20—H20	0.9300
O9—C23	1.336 (2)	C32—C31	1.392 (3)
O9—H9A	0.78 (3)	C32—H32	0.9300
O6—C13	1.223 (2)	C29—C28	1.409 (3)
C9—C10	1.387 (3)	C29—C30	1.410 (3)
C9—H9	0.9300	C27—C28	1.355 (3)
C10—C11	1.385 (3)	C27—H27	0.9300
C10—H10	0.9300	C28—H28	0.9300
N3—C16	1.330 (2)	C31—C30	1.362 (4)
N3—C24	1.372 (2)	C31—H31	0.9300
N3—H3A	0.83 (2)	C30—H30	0.9300
C23—C22	1.375 (3)	O11—C35	1.378 (3)
C23—C24	1.421 (2)	O11—H11A	0.83 (4)
C24—C19	1.407 (3)	C35—H35A	0.9600
C11—H11	0.9300	C35—H35B	0.9600
C16—C17	1.404 (3)	C35—H35C	0.9600
C16—C15	1.487 (3)	O12—H12A	0.82 (3)
C3—C4	1.378 (3)	O12—H12B	0.82 (4)
C3—H3	0.9300

N2—Cu1—N1	174.84 (5)	C16—C15—H15B	109.5
N2—Cu1—O5	77.26 (6)	H15A—C15—H15B	109.5
N1—Cu1—O5	98.34 (6)	C16—C15—H15C	109.5
N2—Cu1—O7	78.01 (6)	H15A—C15—H15C	109.5
N1—Cu1—O7	106.57 (6)	H15B—C15—H15C	109.5
O5—Cu1—O7	154.84 (6)	C3—C4—C5	118.75 (18)
N2—Cu1—O1	100.11 (6)	C3—C4—H4	120.6
N1—Cu1—O1	77.38 (6)	C5—C4—H4	120.6
O5—Cu1—O1	94.25 (6)	C33—O10—H10A	110.9 (19)
O7—Cu1—O1	94.57 (6)	C26—N4—C34	122.97 (16)
N2—Cu1—O3	104.79 (6)	C26—N4—H4A	115.8 (15)
N1—Cu1—O3	77.75 (6)	C34—N4—H4A	121.2 (15)
O5—Cu1—O3	90.63 (6)	C20—C21—C22	121.13 (19)
O7—Cu1—O3	91.22 (6)	C20—C21—H21	119.4
O1—Cu1—O3	155.09 (5)	C22—C21—H21	119.4
C1—N1—C5	120.77 (15)	N4—C26—C27	118.97 (17)
C1—N1—Cu1	119.89 (12)	N4—C26—C25	117.88 (18)
C5—N1—Cu1	119.29 (12)	C27—C26—C25	123.14 (19)
C12—N2—C8	120.70 (15)	C24—C19—C20	119.47 (17)
C12—N2—Cu1	119.15 (12)	C24—C19—C18	117.23 (18)
C8—N2—Cu1	120.15 (11)	C20—C19—C18	123.29 (19)
C13—O5—Cu1	114.39 (11)	O10—C33—C32	125.54 (19)
C7—O3—Cu1	112.59 (12)	O10—C33—C34	116.62 (17)
C6—O1—Cu1	113.61 (11)	C32—C33—C34	117.83 (19)
C14—O7—Cu1	113.22 (11)	C26—C25—H25A	109.5
N1—C1—C2	120.51 (16)	C26—C25—H25B	109.5
N1—C1—C6	114.34 (15)	H25A—C25—H25B	109.5
C2—C1—C6	125.15 (16)	C26—C25—H25C	109.5
N1—C5—C4	121.03 (17)	H25A—C25—H25C	109.5
N1—C5—C7	113.87 (15)	H25B—C25—H25C	109.5
C4—C5—C7	125.08 (16)	C18—C17—C16	120.42 (17)
O3—C7—O4	127.36 (18)	C18—C17—H17	119.8
O3—C7—C5	116.32 (15)	C16—C17—H17	119.8
O4—C7—C5	116.30 (17)	C23—C22—C21	121.22 (19)
O2—C6—O1	126.85 (17)	C23—C22—H22	119.4
O2—C6—C1	118.45 (17)	C21—C22—H22	119.4
O1—C6—C1	114.70 (15)	N4—C34—C29	119.13 (16)
N2—C8—C9	121.44 (15)	N4—C34—C33	119.13 (16)
N2—C8—C13	113.94 (15)	C29—C34—C33	121.73 (17)
C9—C8—C13	124.61 (15)	C17—C18—C19	120.87 (19)
O8—C14—O7	128.10 (17)	C17—C18—H18	119.6
O8—C14—C12	116.60 (16)	C19—C18—H18	119.6
O7—C14—C12	115.30 (14)	C21—C20—C19	119.6 (2)
C3—C2—C1	119.29 (18)	C21—C20—H20	120.2
C3—C2—H2	120.4	C19—C20—H20	120.2
C1—C2—H2	120.4	C33—C32—C31	120.5 (2)
N2—C12—C11	120.58 (16)	C33—C32—H32	119.8
N2—C12—C14	114.29 (15)	C31—C32—H32	119.8
C11—C12—C14	125.13 (15)	C28—C29—C34	117.42 (17)
C23—O9—H9A	111 (2)	C28—C29—C30	124.26 (19)
C8—C9—C10	118.74 (17)	C34—C29—C30	118.31 (19)
C8—C9—H9	120.6	C28—C27—C26	120.44 (19)
C10—C9—H9	120.6	C28—C27—H27	119.8
C11—C10—C9	119.10 (18)	C26—C27—H27	119.8
C11—C10—H10	120.5	C27—C28—C29	121.04 (19)
C9—C10—H10	120.5	C27—C28—H28	119.5
C16—N3—C24	122.87 (16)	C29—C28—H28	119.5
C16—N3—H3A	118.3 (14)	C30—C31—C32	122.37 (19)
C24—N3—H3A	118.8 (14)	C30—C31—H31	118.8
O9—C23—C22	125.73 (17)	C32—C31—H31	118.8
O9—C23—C24	116.22 (16)	C31—C30—C29	119.3 (2)
C22—C23—C24	118.04 (18)	C31—C30—H30	120.3
N3—C24—C19	119.72 (15)	C29—C30—H30	120.3
N3—C24—C23	119.76 (16)	O6—C13—O5	127.45 (17)
C19—C24—C23	120.52 (16)	O6—C13—C8	118.55 (18)
C12—C11—C10	119.43 (16)	O5—C13—C8	113.99 (15)
C12—C11—H11	120.3	C35—O11—H11A	112 (2)
C10—C11—H11	120.3	O11—C35—H35A	109.5
N3—C16—C17	118.85 (18)	O11—C35—H35B	109.5
N3—C16—C15	118.99 (18)	H35A—C35—H35B	109.5
C17—C16—C15	122.15 (16)	O11—C35—H35C	109.5
C4—C3—C2	119.63 (18)	H35A—C35—H35C	109.5
C4—C3—H3	120.2	H35B—C35—H35C	109.5
C2—C3—H3	120.2	H12A—O12—H12B	120 (4)
C16—C15—H15A	109.5

O5—Cu1—N1—C1	−90.30 (13)	Cu1—N2—C12—C14	2.18 (19)
O7—Cu1—N1—C1	93.28 (13)	O8—C14—C12—N2	177.89 (16)
O1—Cu1—N1—C1	2.21 (12)	O7—C14—C12—N2	−1.2 (2)
O3—Cu1—N1—C1	−179.13 (13)	O8—C14—C12—C11	−1.1 (3)
O5—Cu1—N1—C5	87.16 (13)	O7—C14—C12—C11	179.80 (18)
O7—Cu1—N1—C5	−89.26 (13)	N2—C8—C9—C10	−0.5 (3)
O1—Cu1—N1—C5	179.67 (13)	C13—C8—C9—C10	−179.33 (18)
O3—Cu1—N1—C5	−1.67 (12)	C8—C9—C10—C11	0.3 (3)
O5—Cu1—N2—C12	−177.07 (13)	C16—N3—C24—C19	0.8 (3)
O7—Cu1—N2—C12	−1.75 (12)	C16—N3—C24—C23	−179.05 (16)
O1—Cu1—N2—C12	90.82 (13)	O9—C23—C24—N3	0.6 (3)
O3—Cu1—N2—C12	−89.82 (13)	C22—C23—C24—N3	−179.72 (18)
O5—Cu1—N2—C8	3.17 (12)	O9—C23—C24—C19	−179.23 (17)
O7—Cu1—N2—C8	178.49 (13)	C22—C23—C24—C19	0.4 (3)
O1—Cu1—N2—C8	−88.94 (13)	N2—C12—C11—C10	−1.2 (3)
O3—Cu1—N2—C8	90.42 (13)	C14—C12—C11—C10	177.78 (19)
N2—Cu1—O5—C13	−4.78 (13)	C9—C10—C11—C12	0.5 (3)
N1—Cu1—O5—C13	172.49 (13)	C24—N3—C16—C17	1.1 (3)
O7—Cu1—O5—C13	−15.6 (2)	C24—N3—C16—C15	−177.64 (17)
O1—Cu1—O5—C13	94.64 (14)	C1—C2—C3—C4	−0.4 (3)
O3—Cu1—O5—C13	−109.81 (14)	C2—C3—C4—C5	0.0 (3)
N2—Cu1—O3—C7	−171.70 (13)	N1—C5—C4—C3	0.7 (3)
N1—Cu1—O3—C7	3.68 (13)	C7—C5—C4—C3	−177.43 (18)
O5—Cu1—O3—C7	−94.71 (14)	C34—N4—C26—C27	−1.9 (3)
O7—Cu1—O3—C7	110.38 (14)	C34—N4—C26—C25	177.28 (18)
O1—Cu1—O3—C7	6.8 (2)	N3—C24—C19—C20	179.49 (17)
N2—Cu1—O1—C6	172.75 (13)	C23—C24—C19—C20	−0.6 (3)
N1—Cu1—O1—C6	−2.65 (13)	N3—C24—C19—C18	−1.4 (3)
O5—Cu1—O1—C6	94.96 (14)	C23—C24—C19—C18	178.43 (17)
O7—Cu1—O1—C6	−108.63 (14)	N3—C16—C17—C18	−2.3 (3)
O3—Cu1—O1—C6	−5.8 (2)	C15—C16—C17—C18	176.36 (19)
N2—Cu1—O7—C14	1.00 (13)	O9—C23—C22—C21	179.5 (2)
N1—Cu1—O7—C14	−176.57 (13)	C24—C23—C22—C21	−0.1 (3)
O5—Cu1—O7—C14	11.8 (2)	C20—C21—C22—C23	0.1 (4)
O1—Cu1—O7—C14	−98.39 (14)	C26—N4—C34—C29	0.9 (3)
O3—Cu1—O7—C14	105.86 (14)	C26—N4—C34—C33	−177.81 (18)
C5—N1—C1—C2	0.7 (2)	O10—C33—C34—N4	0.0 (3)
Cu1—N1—C1—C2	178.13 (13)	C32—C33—C34—N4	178.91 (18)
C5—N1—C1—C6	−179.02 (14)	O10—C33—C34—C29	−178.76 (18)
Cu1—N1—C1—C6	−1.60 (19)	C32—C33—C34—C29	0.2 (3)
C1—N1—C5—C4	−1.1 (3)	C16—C17—C18—C19	1.7 (3)
Cu1—N1—C5—C4	−178.51 (14)	C24—C19—C18—C17	0.2 (3)
C1—N1—C5—C7	177.25 (14)	C20—C19—C18—C17	179.2 (2)
Cu1—N1—C5—C7	−0.19 (19)	C22—C21—C20—C19	−0.3 (4)
Cu1—O3—C7—O4	174.11 (17)	C24—C19—C20—C21	0.6 (3)
Cu1—O3—C7—C5	−4.8 (2)	C18—C19—C20—C21	−178.4 (2)
N1—C5—C7—O3	3.6 (2)	O10—C33—C32—C31	178.4 (2)
C4—C5—C7—O3	−178.13 (18)	C34—C33—C32—C31	−0.4 (3)
N1—C5—C7—O4	−175.40 (16)	N4—C34—C29—C28	0.8 (3)
C4—C5—C7—O4	2.8 (3)	C33—C34—C29—C28	179.49 (19)
Cu1—O1—C6—O2	−176.75 (17)	N4—C34—C29—C30	−178.67 (17)
Cu1—O1—C6—C1	2.55 (19)	C33—C34—C29—C30	0.1 (3)
N1—C1—C6—O2	178.49 (17)	N4—C26—C27—C28	1.1 (3)
C2—C1—C6—O2	−1.2 (3)	C25—C26—C27—C28	−178.0 (2)
N1—C1—C6—O1	−0.9 (2)	C26—C27—C28—C29	0.6 (3)
C2—C1—C6—O1	179.41 (17)	C34—C29—C28—C27	−1.5 (3)
C12—N2—C8—C9	−0.1 (2)	C30—C29—C28—C27	177.9 (2)
Cu1—N2—C8—C9	179.63 (13)	C33—C32—C31—C30	0.4 (4)
C12—N2—C8—C13	178.78 (14)	C32—C31—C30—C29	−0.2 (4)
Cu1—N2—C8—C13	−1.46 (19)	C28—C29—C30—C31	−179.5 (2)
Cu1—O7—C14—O8	−179.14 (17)	C34—C29—C30—C31	−0.1 (3)
Cu1—O7—C14—C12	−0.18 (19)	Cu1—O5—C13—O6	−175.71 (17)
N1—C1—C2—C3	0.0 (3)	Cu1—O5—C13—C8	5.28 (19)
C6—C1—C2—C3	179.72 (18)	N2—C8—C13—O6	178.03 (17)
C8—N2—C12—C11	1.0 (3)	C9—C8—C13—O6	−3.1 (3)
Cu1—N2—C12—C11	−178.77 (14)	N2—C8—C13—O5	−2.9 (2)
C8—N2—C12—C14	−178.06 (14)	C9—C8—C13—O5	176.01 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O9	0.83 (3)	2.37 (2)	2.692 (2)	104.3 (17)
N3—H3A···O11	0.83 (3)	1.93 (3)	2.739 (3)	164 (2)
N4—H4A···O8ⁱ	0.95 (3)	1.87 (3)	2.723 (2)	149 (2)
O9—H9A···O5	0.78 (3)	1.79 (3)	2.563 (2)	176 (3)
O10—H10A···O4	0.87 (4)	1.70 (4)	2.555 (3)	167 (3)
O11—H11A···O1ⁱ	0.83 (4)	1.88 (4)	2.706 (3)	172 (4)
O12—H12A···O7	0.82 (3)	2.14 (3)	2.895 (3)	154 (4)
O12—H12B···O2ⁱⁱ	0.82 (4)	2.21 (4)	2.974 (3)	156 (4)
C10—H10···O3ⁱⁱⁱ	0.93	2.55	3.177 (3)	125
C15—H15C···O2ⁱ	0.96	2.55	3.480 (3)	163
C17—H17···O6^iv	0.93	2.29	3.185 (3)	161
C25—H25C···O8ⁱ	0.96	2.48	3.212 (3)	133
C27—H27···O2^v	0.93	2.50	3.394 (3)	162

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

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)₂[Cu(C₇H₃NO₄)₂]·CH₄O·H₂O
M_r	764.20
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.116 (2), 12.895 (3), 14.816 (3)
α, β, γ (°)	64.45 (3), 76.23 (3), 83.74 (3)
V (Å³)	1693.5 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.5 × 0.4 × 0.3

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.714, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	18924, 9061, 7185
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.01
No. of reflections	9061
No. of parameters	498
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.45

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O9	0.83 (3)	2.37 (2)	2.692 (2)	104.3 (17)
N3—H3A···O11	0.83 (3)	1.93 (3)	2.739 (3)	164 (2)
N4—H4A···O8ⁱ	0.95 (3)	1.87 (3)	2.723 (2)	149 (2)
O9—H9A···O5	0.78 (3)	1.79 (3)	2.563 (2)	176 (3)
O10—H10A···O4	0.87 (4)	1.70 (4)	2.555 (3)	167 (3)
O11—H11A···O1ⁱ	0.83 (4)	1.88 (4)	2.706 (3)	172 (4)
O12—H12A···O7	0.82 (3)	2.14 (3)	2.895 (3)	154 (4)
O12—H12B···O2ⁱⁱ	0.82 (4)	2.21 (4)	2.974 (3)	156 (4)
C10—H10···O3ⁱⁱⁱ	0.93	2.55	3.177 (3)	125
C15—H15C···O2ⁱ	0.96	2.55	3.480 (3)	163
C17—H17···O6^iv	0.93	2.29	3.185 (3)	161
C25—H25C···O8ⁱ	0.96	2.48	3.212 (3)	133
C27—H27···O2^v	0.93	2.50	3.394 (3)	162

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

Acknowledgements

The authors thank the Faculty of Chemistry, Islamic Azad University, North Tehran Branch, for financial support.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Eshtiagh-Hosseini, H., Aghabozorg, H., Mirzaei, M., Amini, M. M., Chen, Y.-G., Shokrollahi, A. & Aghaei, R. (2010b). J. Mol. Struct. 973, 180–189. CAS Google Scholar
Eshtiagh-Hosseini, H., Alfi, N., Mirzaei, M., Fanwick, P. & Fanwick, P. E. (2010c). Acta Cryst. E66, m1450. Web of Science CSD CrossRef IUCr Journals Google Scholar
Eshtiagh-Hosseini, H., Yousefi, Z., Safiee, M. & Mirzaei, M. (2010a). J. Coord. Chem. 63, 3187–3197. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA and X–SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar

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Volume 67| Part 3| March 2011| Pages m379-m380

doi:10.1107/S160053681100674X

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

Bis(8-hy­dr­oxy-2-methyl­quinolinium) bis­­(pyridine-2,6-di­carboxyl­ato)cuprate(II) methanol monosolvate monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(8-hydroxy-2-methylquinolinium) bis(pyridine-2,6-dicarboxylato)cuprate(II) methanol monosolvate monohydrate