[6-(3,5-Dimethyl-1H-pyrazol-1-yl)picolinato](pyridine-2,6-dicarboxyl­ato)copper(II) dihydrate

Hu, F.-L.; Yin, X.-H.; Zhao, K.; Feng, Y.; Lin, C.-W.

doi:10.1107/S1600536808013731

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m812

doi:10.1107/S1600536808013731

Open

access

[6-(3,5-Dimethyl-1H-pyrazol-1-yl)picolinato](pyridine-2,6-dicarboxylato)copper(II) dihydrate

Fei-Long Hu,^a Xian-Hong Yin,^a ^* Kai Zhao,^b Yu Feng ^a and Cui-Wu Lin ^b

^aCollege of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, People's Republic of China
^*Correspondence e-mail: yxhphd@163.com

(Received 11 January 2008; accepted 8 May 2008; online 14 May 2008)

In the title complex, [Cu(C₇H₄NO₄)(C₁₁H₁₀N₃O₂)]·2H₂O, the Cu^II atom is in a distorted octahedral geometry. The equatorial plane is formed by two N atoms and one O atom from 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate and by one N atom from pyridine-2,6-dicarboxylate (pdc). Two pdc O atoms occupy the axial positions. Water molecules are hydrogen bonded to the complex molecules, forming a two-dimensional sheet structure.

Related literature

For the isostructural Ni derivative of the title compound, see: Feng et al. (2008 ). For other related literature, see: Yin et al. (2007 ); Zhao et al. (2007 ).

Experimental

Crystal data

[Cu(C₇H₄NO₄)(C₁₁H₁₀N₃O₂)]·2H₂O
M_r = 481.90
Triclinic, $[P \overline 1]$
a = 9.0040 (10) Å
b = 9.0360 (10) Å
c = 12.6760 (15) Å
α = 103.932 (3)°
β = 90.289 (2)°
γ = 104.177 (3)°
V = 968.25 (19) Å³
Z = 2
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 298 (2) K
0.39 × 0.35 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.655, T_max = 0.684
5068 measured reflections
3361 independent reflections
2844 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.113
S = 1.03
3361 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O7ⁱ	0.82	1.69	2.477 (4)	159
O7—H7D⋯O8	0.85	1.89	2.637 (4)	145
O7—H7E⋯O6	0.85	1.73	2.524 (4)	154
O8—H8A⋯O5	0.85	2.25	3.020 (4)	152
O8—H8B⋯O2ⁱⁱ	0.85	1.96	2.730 (4)	151
Symmetry codes: (i) x+1, y+1, z; (ii) x, y-1, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808013731/zl2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013731/zl2096Isup2.hkl

checkCIF report

Comment top

Recently we reported the crystal structures of bis(6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato)zinc(II) trihydrate [Yin et al., 2007] and bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]cobalt(II) hemipentahydrate [Zhao et al., 2007]. As a continuation of these investigations, we report here the crystal structure of a new copper(II) complex with the ligand 3-chloro-6-(3,5-dimethyl-1 H-pyrazol-1-yl) picolinic acid (CDPA) and pyridine-2,6-dicarboxylate (PDBL). (Fig.1).

The title compound, (I), consists of a central asymmetric copper(II) complex cation and two uncoordinated water molecules. The compound is isostructural with its Ni derivative [Feng et al., 2008]. In the cation (Fig.1), the Cu atom is six-coordinated by three N atoms and three O atoms from CDPA and PDBL ligands. The three diagonal angles for the Cu(II) octahedron range from 150.7 (4)° to 173.7 (2)°, the dihedral angle between the planes of the two ligands is 80.5 (6)°, which indicates a slightly distorted octahedral geometry around the Cu^IIatom.

Analysis of the crystal packing of the title compound reveals the existence of multiple intermolecular O—H···O hydrogen bonds between the mononuclear subunits and the lattice water molecules (Figure 2), forming a two-dimensional hydrogen-bonded sheet perpendicular to the c-axis of the structure (Figure 3). In this sheet the two interstitial water molecules are connecting three complex molecules with each other: The protonated carboxyl oxygen atom O4 acts as a hydrogen donor towards O7 of one of the water molecules. One of the H atoms of O7 in turn binds with the second water molecule, and each one H atom of both water molecules acts as a hydrogen bonding donor towards the two carboxyl O atoms O5 and O6 of a neighboring complex. The last remaining water H atom (H8b) makes the connection to the third complex connected by the two water molecules (Figure 2). The carboxylate group that acts as an H bond acceptor towards both water molecules via both of its O atoms O5 and O6 exhibits a delocalized π system with nearly identical C—O distances.

Related literature top

For the isostructural Ni derivative of the title compound, see: Feng et al. (2008). For other related literature, see: Yin et al. (2007); Zhao et al. (2007).

Experimental top

3-Chloro-(6-(3,5-dimethyl-1H-pyrazol-1-yl))picolinic acid, pyridine-2,6-dicarboxylic acid and CuCl₂.6H₂O were available commercially and were used without further purification. Equimolar amounts of 3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl) picolinic acid (0.5 mmol, 125 mg) and pyridine-2,6-dicarboxylic acid (0.5 mmol, 83 mg) were dissolved in anhydrous alcohol (15 ml). The mixture was stirred to give a clear solution, to this solution was added CuCl₂.6H₂O (0.5 mmol, 113 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, blue prisms of the title compound were formed. The crystals were isolated, washed with alcohol three times and dried in a vacuum desiccator using silica gel (Yield 75%). Elemental analysis: found: C, 44.85; H, 3.78; N, 11.65%. calc. for C₁₈H₁₈CuN₄O₈: C, 44.86; H, 3.76; N, 11.63%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound (I) showing 50% proability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Detail of (I), showing the O—H···O hydrogen bonds. Displacement ellipsoids are drawn at the 50% probability level and the hydrogen bonds are indiacted by dashed lines. [Symmetry codes:(i) x, -1+y, z; (ii) -1+x, -1+y, z.]
	Fig. 3. Crystal packing of (I) showing the hydrogen bonding interactions.

[6-(3,5-Dimethyl-1H-pyrazol-1-yl)picolinato](pyridine-2,6- dicarboxylato)copper(II) dihydrate top

Crystal data top

[Cu(C₇H₄NO₄)(C₁₁H₁₀N₃O₂)]·2H₂O	Z = 2
M_r = 481.90	F(000) = 494
Triclinic, P1	D_x = 1.653 Mg m⁻³
a = 9.004 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.036 (1) Å	Cell parameters from 3268 reflections
c = 12.6760 (15) Å	θ = 2.3–27.8°
α = 103.932 (3)°	µ = 1.19 mm⁻¹
β = 90.289 (2)°	T = 298 K
γ = 104.177 (3)°	Block, blue
V = 968.25 (19) Å³	0.39 × 0.35 × 0.32 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3361 independent reflections
Radiation source: fine-focus sealed tube	2844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→6
T_min = 0.655, T_max = 0.684	k = −10→10
5068 measured reflections	l = −14→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0647P)² + 0.7713P] where P = (F_o² + 2F_c²)/3
3361 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Cu(C₇H₄NO₄)(C₁₁H₁₀N₃O₂)]·2H₂O	γ = 104.177 (3)°
M_r = 481.90	V = 968.25 (19) Å³
Triclinic, P1	Z = 2
a = 9.004 (1) Å	Mo Kα radiation
b = 9.036 (1) Å	µ = 1.19 mm⁻¹
c = 12.6760 (15) Å	T = 298 K
α = 103.932 (3)°	0.39 × 0.35 × 0.32 mm
β = 90.289 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3361 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2844 reflections with I > 2σ(I)
T_min = 0.655, T_max = 0.684	R_int = 0.014
5068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
3361 reflections	Δρ_min = −0.30 e Å⁻³
280 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	0.72104 (5)	0.95250 (5)	0.26981 (3)	0.03369 (16)
N1	0.7309 (3)	0.9975 (3)	0.4271 (2)	0.0318 (6)
N2	0.8342 (3)	0.7887 (3)	0.4100 (2)	0.0358 (6)
N3	0.8359 (3)	0.7890 (3)	0.3006 (2)	0.0350 (6)
N4	0.6970 (3)	0.9233 (3)	0.1106 (2)	0.0296 (6)
O1	0.6153 (3)	1.1315 (3)	0.3022 (2)	0.0476 (6)
O2	0.5465 (4)	1.2990 (4)	0.4420 (2)	0.0662 (8)
O3	0.9435 (3)	1.1261 (3)	0.2279 (2)	0.0472 (7)
O4	1.0063 (3)	1.2352 (3)	0.0888 (2)	0.0578 (8)
H4	1.0757	1.2945	0.1323	0.087*
O5	0.5089 (3)	0.7472 (3)	0.21665 (19)	0.0498 (7)
O6	0.3550 (4)	0.6217 (4)	0.0688 (2)	0.0735 (10)
O7	0.2133 (3)	0.4600 (3)	0.1912 (2)	0.0576 (7)
H7D	0.2617	0.4484	0.2451	0.069*
H7E	0.2754	0.4928	0.1467	0.069*
O8	0.4582 (4)	0.4587 (4)	0.3057 (3)	0.0964 (13)
H8A	0.5002	0.5498	0.2972	0.116*
H8B	0.5112	0.4395	0.3540	0.116*
C1	0.6077 (4)	1.1920 (4)	0.4025 (3)	0.0419 (8)
C2	0.6808 (4)	1.1214 (4)	0.4800 (3)	0.0359 (8)
C3	0.6976 (4)	1.1722 (4)	0.5913 (3)	0.0459 (9)
H3	0.6632	1.2585	0.6279	0.055*
C4	0.7675 (4)	1.0906 (5)	0.6474 (3)	0.0463 (9)
H4A	0.7813	1.1239	0.7230	0.056*
C5	0.8171 (4)	0.9614 (4)	0.5940 (3)	0.0427 (9)
H5	0.8637	0.9066	0.6318	0.051*
C6	0.7943 (4)	0.9166 (4)	0.4808 (3)	0.0337 (7)
C7	0.8598 (6)	0.6154 (5)	0.5339 (3)	0.0578 (11)
H7A	0.8610	0.5071	0.5244	0.087*
H7B	0.7682	0.6328	0.5675	0.087*
H7C	0.9481	0.6821	0.5795	0.087*
C8	0.8633 (4)	0.6533 (4)	0.4257 (3)	0.0402 (8)
C9	0.8869 (5)	0.5692 (5)	0.3260 (3)	0.0474 (9)
H9	0.9105	0.4719	0.3103	0.057*
C10	0.8691 (4)	0.6564 (4)	0.2504 (3)	0.0394 (8)
C11	0.8836 (5)	0.6158 (5)	0.1306 (3)	0.0558 (11)
H11A	0.8756	0.7030	0.1020	0.084*
H11B	0.8031	0.5247	0.0967	0.084*
H11C	0.9814	0.5936	0.1158	0.084*
C12	0.9239 (4)	1.1361 (4)	0.1343 (3)	0.0354 (8)
C13	0.7922 (4)	1.0210 (4)	0.0612 (3)	0.0325 (7)
C14	0.7664 (4)	1.0143 (4)	−0.0471 (3)	0.0418 (8)
H14	0.8322	1.0841	−0.0797	0.050*
C15	0.6420 (5)	0.9030 (5)	−0.1072 (3)	0.0460 (9)
H15	0.6246	0.8957	−0.1809	0.055*
C16	0.5451 (4)	0.8038 (4)	−0.0566 (3)	0.0437 (9)
H16	0.4605	0.7286	−0.0953	0.052*
C17	0.5747 (4)	0.8171 (4)	0.0524 (3)	0.0350 (8)
C18	0.4718 (4)	0.7214 (4)	0.1191 (3)	0.0404 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0395 (3)	0.0366 (2)	0.0240 (2)	0.00751 (18)	−0.00296 (16)	0.00805 (16)
N1	0.0295 (15)	0.0370 (15)	0.0271 (14)	0.0050 (12)	−0.0005 (11)	0.0082 (11)
N2	0.0410 (16)	0.0431 (16)	0.0251 (14)	0.0105 (13)	−0.0025 (12)	0.0124 (12)
N3	0.0421 (17)	0.0390 (15)	0.0244 (14)	0.0096 (13)	−0.0014 (12)	0.0099 (12)
N4	0.0303 (14)	0.0297 (13)	0.0268 (14)	0.0040 (11)	−0.0029 (11)	0.0072 (11)
O1	0.0601 (17)	0.0491 (15)	0.0353 (14)	0.0208 (13)	−0.0082 (12)	0.0070 (11)
O2	0.083 (2)	0.0616 (18)	0.0598 (19)	0.0395 (17)	−0.0055 (16)	0.0045 (15)
O3	0.0454 (15)	0.0490 (15)	0.0385 (15)	−0.0078 (12)	−0.0113 (12)	0.0148 (11)
O4	0.0518 (17)	0.0564 (16)	0.0536 (17)	−0.0187 (14)	−0.0063 (13)	0.0252 (13)
O5	0.0479 (15)	0.0552 (15)	0.0326 (14)	−0.0134 (13)	−0.0022 (11)	0.0122 (11)
O6	0.066 (2)	0.077 (2)	0.0546 (18)	−0.0361 (17)	−0.0245 (15)	0.0292 (16)
O7	0.0581 (18)	0.0593 (17)	0.0539 (17)	0.0052 (14)	−0.0020 (14)	0.0211 (14)
O8	0.076 (2)	0.074 (2)	0.147 (4)	0.0085 (19)	−0.033 (2)	0.055 (2)
C1	0.040 (2)	0.0373 (19)	0.045 (2)	0.0083 (16)	−0.0040 (16)	0.0062 (16)
C2	0.0344 (19)	0.0364 (18)	0.0319 (18)	0.0025 (15)	0.0008 (14)	0.0058 (14)
C3	0.053 (2)	0.044 (2)	0.0331 (19)	0.0061 (18)	0.0057 (17)	0.0002 (16)
C4	0.050 (2)	0.057 (2)	0.0234 (17)	0.0041 (19)	0.0008 (16)	0.0042 (16)
C5	0.045 (2)	0.053 (2)	0.0295 (18)	0.0078 (18)	−0.0021 (16)	0.0146 (16)
C6	0.0324 (18)	0.0396 (18)	0.0292 (17)	0.0057 (15)	−0.0008 (14)	0.0122 (14)
C7	0.079 (3)	0.057 (2)	0.045 (2)	0.021 (2)	−0.001 (2)	0.0243 (19)
C8	0.039 (2)	0.044 (2)	0.041 (2)	0.0103 (16)	−0.0043 (16)	0.0179 (16)
C9	0.058 (3)	0.043 (2)	0.044 (2)	0.0169 (18)	−0.0040 (18)	0.0120 (17)
C10	0.040 (2)	0.045 (2)	0.0324 (18)	0.0115 (16)	−0.0030 (15)	0.0074 (15)
C11	0.075 (3)	0.059 (2)	0.036 (2)	0.025 (2)	0.002 (2)	0.0070 (18)
C12	0.0322 (18)	0.0374 (18)	0.0367 (19)	0.0032 (15)	−0.0038 (15)	0.0151 (15)
C13	0.0334 (18)	0.0354 (17)	0.0299 (17)	0.0070 (14)	0.0002 (14)	0.0121 (14)
C14	0.045 (2)	0.048 (2)	0.0338 (19)	0.0052 (17)	0.0028 (16)	0.0183 (16)
C15	0.054 (2)	0.057 (2)	0.0253 (17)	0.0098 (19)	−0.0060 (16)	0.0118 (16)
C16	0.047 (2)	0.048 (2)	0.0294 (18)	0.0035 (17)	−0.0093 (16)	0.0054 (15)
C17	0.041 (2)	0.0312 (17)	0.0300 (17)	0.0064 (15)	−0.0037 (15)	0.0052 (14)
C18	0.040 (2)	0.0379 (18)	0.037 (2)	−0.0032 (16)	−0.0065 (16)	0.0101 (15)

Geometric parameters (Å, º) top

Cu1—N1	1.934 (3)	C3—C4	1.387 (5)
Cu1—N4	1.975 (3)	C3—H3	0.9300
Cu1—O1	2.032 (3)	C4—C5	1.377 (5)
Cu1—N3	2.104 (3)	C4—H4A	0.9300
Cu1—O5	2.279 (2)	C5—C6	1.394 (5)
Cu1—O3	2.372 (2)	C5—H5	0.9300
N1—C6	1.327 (4)	C7—C8	1.490 (5)
N1—C2	1.340 (4)	C7—H7A	0.9600
N2—C8	1.370 (4)	C7—H7B	0.9600
N2—N3	1.388 (4)	C7—H7C	0.9600
N2—C6	1.406 (4)	C8—C9	1.357 (5)
N3—C10	1.318 (4)	C9—C10	1.410 (5)
N4—C13	1.344 (4)	C9—H9	0.9300
N4—C17	1.345 (4)	C10—C11	1.489 (5)
O1—C1	1.266 (4)	C11—H11A	0.9600
O2—C1	1.233 (4)	C11—H11B	0.9600
O3—C12	1.226 (4)	C11—H11C	0.9600
O4—C12	1.269 (4)	C12—C13	1.505 (5)
O4—H4	0.8200	C13—C14	1.376 (5)
O5—C18	1.230 (4)	C14—C15	1.385 (5)
O6—C18	1.256 (4)	C14—H14	0.9300
O7—H7D	0.8498	C15—C16	1.369 (5)
O7—H7E	0.8498	C15—H15	0.9300
O8—H8A	0.8500	C16—C17	1.377 (5)
O8—H8B	0.8500	C16—H16	0.9300
C1—C2	1.519 (5)	C17—C18	1.512 (5)
C2—C3	1.370 (5)

N1—Cu1—N4	173.70 (11)	C6—C5—H5	121.5
N1—Cu1—O1	80.55 (11)	N1—C6—C5	121.3 (3)
N4—Cu1—O1	93.19 (10)	N1—C6—N2	112.0 (3)
N1—Cu1—N3	77.82 (11)	C5—C6—N2	126.8 (3)
N4—Cu1—N3	108.45 (10)	C8—C7—H7A	109.5
O1—Cu1—N3	158.36 (10)	C8—C7—H7B	109.5
N1—Cu1—O5	103.92 (10)	H7A—C7—H7B	109.5
N4—Cu1—O5	76.16 (10)	C8—C7—H7C	109.5
O1—Cu1—O5	98.55 (11)	H7A—C7—H7C	109.5
N3—Cu1—O5	87.33 (11)	H7B—C7—H7C	109.5
N1—Cu1—O3	105.16 (10)	C9—C8—N2	106.0 (3)
N4—Cu1—O3	75.33 (9)	C9—C8—C7	130.9 (3)
O1—Cu1—O3	89.65 (11)	N2—C8—C7	123.1 (3)
N3—Cu1—O3	95.34 (10)	C8—C9—C10	107.4 (3)
O5—Cu1—O3	150.70 (9)	C8—C9—H9	126.3
C6—N1—C2	121.3 (3)	C10—C9—H9	126.3
C6—N1—Cu1	121.7 (2)	N3—C10—C9	110.2 (3)
C2—N1—Cu1	116.9 (2)	N3—C10—C11	121.2 (3)
C8—N2—N3	110.9 (3)	C9—C10—C11	128.5 (3)
C8—N2—C6	132.6 (3)	C10—C11—H11A	109.5
N3—N2—C6	116.4 (3)	C10—C11—H11B	109.5
C10—N3—N2	105.5 (3)	H11A—C11—H11B	109.5
C10—N3—Cu1	140.2 (2)	C10—C11—H11C	109.5
N2—N3—Cu1	110.3 (2)	H11A—C11—H11C	109.5
C13—N4—C17	119.1 (3)	H11B—C11—H11C	109.5
C13—N4—Cu1	120.4 (2)	O3—C12—O4	126.6 (3)
C17—N4—Cu1	120.1 (2)	O3—C12—C13	119.5 (3)
C1—O1—Cu1	114.9 (2)	O4—C12—C13	113.9 (3)
C12—O3—Cu1	108.3 (2)	N4—C13—C14	121.2 (3)
C12—O4—H4	109.5	N4—C13—C12	114.5 (3)
C18—O5—Cu1	111.8 (2)	C14—C13—C12	124.3 (3)
H7D—O7—H7E	110.6	C13—C14—C15	119.6 (3)
H8A—O8—H8B	109.0	C13—C14—H14	120.2
O2—C1—O1	126.8 (4)	C15—C14—H14	120.2
O2—C1—C2	118.0 (3)	C16—C15—C14	119.0 (3)
O1—C1—C2	115.1 (3)	C16—C15—H15	120.5
N1—C2—C3	121.1 (3)	C14—C15—H15	120.5
N1—C2—C1	112.1 (3)	C15—C16—C17	119.0 (3)
C3—C2—C1	126.7 (3)	C15—C16—H16	120.5
C2—C3—C4	117.7 (3)	C17—C16—H16	120.5
C2—C3—H3	121.1	N4—C17—C16	122.1 (3)
C4—C3—H3	121.1	N4—C17—C18	113.7 (3)
C5—C4—C3	121.6 (3)	C16—C17—C18	124.2 (3)
C5—C4—H4A	119.2	O5—C18—O6	125.8 (3)
C3—C4—H4A	119.2	O5—C18—C17	117.9 (3)
C4—C5—C6	116.9 (3)	O6—C18—C17	116.2 (3)
C4—C5—H5	121.5

O1—Cu1—N1—C6	179.7 (3)	O1—C1—C2—C3	175.1 (3)
N3—Cu1—N1—C6	−1.0 (3)	N1—C2—C3—C4	−0.3 (5)
O5—Cu1—N1—C6	83.1 (3)	C1—C2—C3—C4	179.8 (3)
O3—Cu1—N1—C6	−93.3 (3)	C2—C3—C4—C5	−0.8 (6)
O1—Cu1—N1—C2	−5.0 (2)	C3—C4—C5—C6	0.2 (5)
N3—Cu1—N1—C2	174.3 (3)	C2—N1—C6—C5	−2.7 (5)
O5—Cu1—N1—C2	−101.6 (2)	Cu1—N1—C6—C5	172.4 (2)
O3—Cu1—N1—C2	82.0 (2)	C2—N1—C6—N2	178.1 (3)
C8—N2—N3—C10	−1.3 (4)	Cu1—N1—C6—N2	−6.8 (4)
C6—N2—N3—C10	−177.3 (3)	C4—C5—C6—N1	1.5 (5)
C8—N2—N3—Cu1	160.9 (2)	C4—C5—C6—N2	−179.4 (3)
C6—N2—N3—Cu1	−15.0 (3)	C8—N2—C6—N1	−160.3 (3)
N1—Cu1—N3—C10	161.2 (4)	N3—N2—C6—N1	14.5 (4)
N4—Cu1—N3—C10	−18.1 (4)	C8—N2—C6—C5	20.6 (6)
O1—Cu1—N3—C10	163.0 (3)	N3—N2—C6—C5	−164.6 (3)
O5—Cu1—N3—C10	56.4 (4)	N3—N2—C8—C9	1.4 (4)
O3—Cu1—N3—C10	−94.4 (4)	C6—N2—C8—C9	176.4 (4)
N1—Cu1—N3—N2	8.5 (2)	N3—N2—C8—C7	−176.3 (3)
N4—Cu1—N3—N2	−170.80 (19)	C6—N2—C8—C7	−1.3 (6)
O1—Cu1—N3—N2	10.3 (4)	N2—C8—C9—C10	−0.8 (4)
O5—Cu1—N3—N2	−96.3 (2)	C7—C8—C9—C10	176.6 (4)
O3—Cu1—N3—N2	112.9 (2)	N2—N3—C10—C9	0.8 (4)
O1—Cu1—N4—C13	79.0 (3)	Cu1—N3—C10—C9	−152.7 (3)
N3—Cu1—N4—C13	−100.6 (3)	N2—N3—C10—C11	−179.0 (3)
O5—Cu1—N4—C13	177.0 (3)	Cu1—N3—C10—C11	27.5 (6)
O3—Cu1—N4—C13	−9.8 (2)	C8—C9—C10—N3	0.0 (4)
O1—Cu1—N4—C17	−93.3 (2)	C8—C9—C10—C11	179.8 (4)
N3—Cu1—N4—C17	87.1 (3)	Cu1—O3—C12—O4	168.4 (3)
O5—Cu1—N4—C17	4.7 (2)	Cu1—O3—C12—C13	−12.6 (4)
O3—Cu1—N4—C17	177.9 (3)	C17—N4—C13—C14	0.1 (5)
N1—Cu1—O1—C1	2.1 (3)	Cu1—N4—C13—C14	−172.3 (3)
N4—Cu1—O1—C1	−178.6 (3)	C17—N4—C13—C12	179.3 (3)
N3—Cu1—O1—C1	0.4 (5)	Cu1—N4—C13—C12	6.9 (4)
O5—Cu1—O1—C1	104.9 (3)	O3—C12—C13—N4	5.8 (5)
O3—Cu1—O1—C1	−103.3 (3)	O4—C12—C13—N4	−175.1 (3)
N1—Cu1—O3—C12	−161.4 (2)	O3—C12—C13—C14	−175.0 (3)
N4—Cu1—O3—C12	12.1 (2)	O4—C12—C13—C14	4.1 (5)
O1—Cu1—O3—C12	−81.3 (2)	N4—C13—C14—C15	−1.3 (5)
N3—Cu1—O3—C12	119.8 (2)	C12—C13—C14—C15	179.6 (3)
O5—Cu1—O3—C12	25.8 (4)	C13—C14—C15—C16	1.4 (6)
N1—Cu1—O5—C18	168.6 (3)	C14—C15—C16—C17	−0.4 (6)
N4—Cu1—O5—C18	−4.9 (3)	C13—N4—C17—C16	0.9 (5)
O1—Cu1—O5—C18	86.3 (3)	Cu1—N4—C17—C16	173.3 (3)
N3—Cu1—O5—C18	−114.6 (3)	C13—N4—C17—C18	−176.4 (3)
O3—Cu1—O5—C18	−18.5 (4)	Cu1—N4—C17—C18	−4.0 (4)
Cu1—O1—C1—O2	−178.3 (3)	C15—C16—C17—N4	−0.8 (6)
Cu1—O1—C1—C2	0.8 (4)	C15—C16—C17—C18	176.3 (4)
C6—N1—C2—C3	2.0 (5)	Cu1—O5—C18—O6	−175.8 (4)
Cu1—N1—C2—C3	−173.3 (3)	Cu1—O5—C18—C17	4.4 (4)
C6—N1—C2—C1	−178.0 (3)	N4—C17—C18—O5	−0.8 (5)
Cu1—N1—C2—C1	6.7 (4)	C16—C17—C18—O5	−178.1 (4)
O2—C1—C2—N1	174.4 (3)	N4—C17—C18—O6	179.3 (3)
O1—C1—C2—N1	−4.8 (4)	C16—C17—C18—O6	2.0 (6)
O2—C1—C2—C3	−5.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O7ⁱ	0.82	1.69	2.477 (4)	159
O7—H7D···O8	0.85	1.89	2.637 (4)	145
O7—H7E···O6	0.85	1.73	2.524 (4)	154
O8—H8A···O5	0.85	2.25	3.020 (4)	152
O8—H8B···O2ⁱⁱ	0.85	1.96	2.730 (4)	151

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

Experimental details

Crystal data
Chemical formula	[Cu(C₇H₄NO₄)(C₁₁H₁₀N₃O₂)]·2H₂O
M_r	481.90
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.004 (1), 9.036 (1), 12.6760 (15)
α, β, γ (°)	103.932 (3), 90.289 (2), 104.177 (3)
V (Å³)	968.25 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.39 × 0.35 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.655, 0.684
No. of measured, independent and observed [I > 2σ(I)] reflections	5068, 3361, 2844
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.03
No. of reflections	3361
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.30

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O7ⁱ	0.82	1.69	2.477 (4)	158.8
O7—H7D···O8	0.85	1.89	2.637 (4)	144.8
O7—H7E···O6	0.85	1.73	2.524 (4)	154.4
O8—H8A···O5	0.85	2.25	3.020 (4)	151.5
O8—H8B···O2ⁱⁱ	0.85	1.96	2.730 (4)	150.5

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

Acknowledgements

The authors thank the Ministry of Education, Science and Technology Key Projects, P. R. China, for research grant No. 205121.

References

Feng, Y., Zhao, K., Yin, X.-H., Zhu, J. & Lin, C.-W. (2008). Acta Cryst. E64, m191. Web of Science CSD CrossRef IUCr Journals 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
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yin, X.-H., Zhao, K., Feng, Y. & Zhu, J. (2007). Acta Cryst. E63, m2926. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhao, K., Yin, X.-H., Feng, Y. & Zhu, J. (2007). Acta Cryst. E63, m3024. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m812

doi:10.1107/S1600536808013731

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

[6-(3,5-Di­methyl-1H-pyrazol-1-yl)picolinato](pyridine-2,6-di­carboxyl­ato)copper(II) dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[6-(3,5-Dimethyl-1H-pyrazol-1-yl)picolinato](pyridine-2,6-dicarboxylato)copper(II) dihydrate