catena-Poly[[[diaqua­copper(II)]-μ-quinoline-2,3-dicarboxyl­ato-κ3N,O2:O3] monohydrate]

Xia, Q.-H.; Guo, Z.-F.; Liu, L.; Wang, Z.; Li, B.

doi:10.1107/S1600536812043206

metal-organic compounds

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Volume 68| Part 11| November 2012| Page m1395

doi:10.1107/S1600536812043206

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catena-Poly[[[diaquacopper(II)]-μ-quinoline-2,3-dicarboxylato-κ³N,O²:O³] monohydrate]

Qiao-Hua Xia,^a Zhong-Fu Guo,^a Li Liu,^a Zhi-kun Wang ^a and Bing Li ^a ^*

^aCollege of Sciences, Zhejiang A&F University, Lin'an, Hangzhou, Zhejiang 311300, People's Republic of China
^*Correspondence e-mail: libingzjfc@163.com

(Received 27 August 2012; accepted 17 October 2012; online 20 October 2012)

In the title compound, {[Cu(C₁₁H₅NO₄)(H₂O)₂]·H₂O}_n, the Cu^II ion is five-coordinated by two O atoms and one N atom of two symmetry-related quinoline-2,3-dicarboxylate ligands, and two water molecules. The water molecules occupy basal and apical positions of the square-pyramidal coordination polyhedron. Each quinoline-2,3-dicarboxylate dianion bridges two adjacent Cu^II ions, forming a polymeric chain along [010]. The chains are further connected via O—H⋯O hydrogen-bonding interactions and quinoline ring π–π interactions [centroid–centroid distance = 3.725 (4) Å], generating a three-dimensional structure. Lattice water molecules participate in the crystal structure via O—H⋯O hydrogen bonds.

Related literature

For background to complexes based on quinoline-2,3-dicarboxylic acid, see: Li & Liu (2010 ).

Experimental

Crystal data

[Cu(C₁₁H₅NO₄)(H₂O)₂]·H₂O
M_r = 332.76
Triclinic, $[P \overline 1]$
a = 7.0284 (14) Å
b = 7.5836 (15) Å
c = 13.276 (3) Å
α = 104.74 (3)°
β = 91.19 (3)°
γ = 116.03 (3)°
V = 607.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.83 mm⁻¹
T = 293 K
0.43 × 0.34 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.763, T_max = 0.854
5813 measured reflections
2696 independent reflections
2382 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.10
2696 reflections
199 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.74 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW1—H1⋯OW3ⁱ	0.81 (2)	2.11 (2)	2.916 (4)	177 (4)
OW1—H2⋯O3ⁱ	0.81 (2)	2.15 (2)	2.944 (3)	166 (5)
OW2—H3⋯O1ⁱⁱ	0.87 (2)	2.12 (2)	2.962 (3)	163 (4)
OW2—H4⋯O2ⁱⁱⁱ	0.89 (2)	2.29 (2)	3.174 (3)	178 (4)
OW3—H5⋯O1^iv	0.82 (2)	1.96 (2)	2.775 (4)	170 (5)
OW3—H6⋯O3ⁱⁱ	0.80 (2)	2.12 (2)	2.909 (3)	169 (5)
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812043206/bh2454sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043206/bh2454Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title complex contains one Cu^II ion, one quinoline-2,3-dicarboxylate dianion, two coordinated water molecules and one lattice water molecule (Fig. 1). The Cu^II ion is five-coordinated within a square-pyramidal [CuNO₄]coordination geometry. Five coordination arises from two O atoms and one N atom belonging to two 2,3-quinolinedicarboxylate ligands (Li & Liu, 2010), and two water molecules. The Cu—O bond lengths vary from 1.9403 (19) to 2.320 (3) Å, and the Cu—N distance is 2.096 (2) Å. Each Cu^II ion interacts with adjacent Cu^II via the bridging mode of the dianion, forming a one-dimensional framework. The resulting chains are further connected through O—H···O hydrogen bonding interactions between the O atoms of quinoline-2,3-dicarboxylate dianion, coordinated water molecules and one lattice water molecule [O···O separations in the range 2.775 (4)–3.174 (3) Å]. Additionally, π–π [3.725 (4) Å] interactions between quinoline rings are involved in the formation of the three-dimensional supramolecular structure (Fig. 2). The shortest Cu···Cu separation along the polymeric chain is 7.5836 (2) Å.

Related literature top

For background to complexes based on 2,3-quinolinedicarboxylic acid, see: Li & Liu (2010).

Experimental top

All commercially obtained reagent grade chemicals were used without further purification. A mixture of copper chloride dihydrate (0.1708 g, 1 mmol) and 2,3-quinolinedicarboxylic acid (0.2171 g, 1 mmol) was added into 20 ml of water with few drops of ammonia solution, and then stirred for 1 h. After 2 days, blue crystals of the title complex were collected by filtration, washed with distilled water, and dried in air.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, with 50% probability displacement ellipsoids for non-H atoms. Symmetry codes: (A) x, -1 + y, z; (B) x, -2 + y, z.
	Fig. 2. Crystal packing diagram for the title compound. All atoms are shown as isotropic spheres of arbitrary size. H atoms bonded to C atoms are omitted for clarity. The H-bonding interactions are shown as red dashed lines.

catena-Poly[[[diaquacopper(II)]-µ-quinoline-2,3-dicarboxylato- κ³N,O²:O³] monohydrate] top

Crystal data top

[Cu(C₁₁H₅NO₄)(H₂O)₂]·H₂O	Z = 2
M_r = 332.76	F(000) = 338
Triclinic, P1	D_x = 1.818 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0284 (14) Å	Cell parameters from 5355 reflections
b = 7.5836 (15) Å	θ = 3.1–27.5°
c = 13.276 (3) Å	µ = 1.83 mm⁻¹
α = 104.74 (3)°	T = 293 K
β = 91.19 (3)°	Block, blue
γ = 116.03 (3)°	0.43 × 0.34 × 0.20 mm
V = 607.7 (2) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2696 independent reflections
Radiation source: fine-focus sealed tube	2382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→9
T_min = 0.763, T_max = 0.854	k = −9→8
5813 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0501P)² + 0.4308P] where P = (F_o² + 2F_c²)/3
2696 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.73 e Å⁻³
10 restraints	Δρ_min = −0.74 e Å⁻³
0 constraints

Crystal data top

[Cu(C₁₁H₅NO₄)(H₂O)₂]·H₂O	γ = 116.03 (3)°
M_r = 332.76	V = 607.7 (2) Å³
Triclinic, P1	Z = 2
a = 7.0284 (14) Å	Mo Kα radiation
b = 7.5836 (15) Å	µ = 1.83 mm⁻¹
c = 13.276 (3) Å	T = 293 K
α = 104.74 (3)°	0.43 × 0.34 × 0.20 mm
β = 91.19 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2696 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2382 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.854	R_int = 0.048
5813 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	10 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.73 e Å⁻³
2696 reflections	Δρ_min = −0.74 e Å⁻³
199 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu	0.30340 (5)	0.43833 (4)	0.17117 (2)	0.02367 (13)
O1	0.2017 (5)	0.8429 (3)	0.07483 (18)	0.0454 (6)
O2	0.3062 (4)	0.6111 (3)	0.08503 (16)	0.0323 (5)
O3	−0.0584 (3)	1.0076 (3)	0.20096 (18)	0.0351 (5)
O4	0.2863 (3)	1.2456 (3)	0.24768 (16)	0.0279 (4)
OW1	0.6719 (4)	0.5956 (4)	0.2208 (2)	0.0448 (6)
H1	0.723 (7)	0.518 (5)	0.198 (4)	0.067*
H2	0.733 (7)	0.701 (4)	0.205 (4)	0.067*
OW2	0.2962 (5)	0.2398 (4)	0.0373 (2)	0.0465 (6)
H3	0.292 (7)	0.126 (5)	0.042 (4)	0.070*
H4	0.406 (6)	0.284 (6)	0.003 (4)	0.070*
OW3	−0.1618 (5)	0.3035 (4)	0.1425 (2)	0.0516 (7)
H5	−0.185 (8)	0.265 (7)	0.0779 (15)	0.077*
H6	−0.140 (8)	0.226 (6)	0.166 (3)	0.077*
N	0.2639 (3)	0.6617 (3)	0.28625 (17)	0.0193 (4)
C1	0.1293 (4)	1.0719 (4)	0.2397 (2)	0.0229 (5)
C2	0.1836 (4)	0.9435 (4)	0.2947 (2)	0.0195 (5)
C3	0.1917 (4)	0.9836 (4)	0.4014 (2)	0.0216 (5)
H3A	0.1706	1.0930	0.4396	0.026*
C4	0.2314 (4)	0.8615 (4)	0.4539 (2)	0.0208 (5)
C5	0.2409 (4)	0.8966 (4)	0.5644 (2)	0.0259 (6)
H5A	0.2254	1.0074	0.6055	0.031*
C6	0.2726 (5)	0.7685 (5)	0.6109 (2)	0.0306 (6)
H6A	0.2771	0.7918	0.6833	0.037*
C7	0.2985 (5)	0.6019 (5)	0.5502 (2)	0.0312 (6)
H7A	0.3172	0.5143	0.5827	0.037*
C8	0.2966 (5)	0.5668 (4)	0.4442 (2)	0.0277 (6)
H8A	0.3183	0.4581	0.4056	0.033*
C9	0.2620 (4)	0.6941 (4)	0.3922 (2)	0.0200 (5)
C10	0.2271 (4)	0.7826 (4)	0.2399 (2)	0.0201 (5)
C11	0.2456 (5)	0.7447 (4)	0.1240 (2)	0.0255 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu	0.0347 (2)	0.02115 (19)	0.0221 (2)	0.01646 (16)	0.00703 (14)	0.01064 (13)
O1	0.095 (2)	0.0415 (12)	0.0239 (12)	0.0488 (14)	0.0131 (12)	0.0165 (9)
O2	0.0555 (13)	0.0351 (11)	0.0250 (11)	0.0322 (11)	0.0176 (10)	0.0170 (9)
O3	0.0349 (11)	0.0418 (12)	0.0381 (13)	0.0222 (10)	0.0005 (9)	0.0186 (10)
O4	0.0396 (11)	0.0189 (9)	0.0266 (11)	0.0122 (9)	0.0022 (8)	0.0112 (8)
OW1	0.0312 (12)	0.0355 (12)	0.0668 (19)	0.0131 (11)	0.0090 (11)	0.0173 (12)
OW2	0.0751 (18)	0.0352 (12)	0.0353 (12)	0.0300 (13)	0.0176 (12)	0.0108 (8)
OW3	0.084 (2)	0.0524 (15)	0.0269 (13)	0.0385 (15)	0.0068 (13)	0.0121 (11)
N	0.0243 (10)	0.0177 (10)	0.0182 (11)	0.0109 (9)	0.0034 (8)	0.0071 (8)
C1	0.0340 (14)	0.0258 (13)	0.0168 (13)	0.0200 (12)	0.0052 (10)	0.0071 (10)
C2	0.0198 (11)	0.0191 (11)	0.0223 (13)	0.0092 (10)	0.0029 (9)	0.0099 (9)
C3	0.0235 (12)	0.0233 (12)	0.0217 (14)	0.0138 (11)	0.0042 (10)	0.0072 (10)
C4	0.0171 (11)	0.0252 (12)	0.0224 (14)	0.0100 (10)	0.0044 (9)	0.0100 (10)
C5	0.0257 (13)	0.0348 (14)	0.0221 (14)	0.0170 (12)	0.0064 (10)	0.0103 (11)
C6	0.0302 (14)	0.0482 (17)	0.0208 (14)	0.0203 (14)	0.0078 (11)	0.0176 (12)
C7	0.0339 (15)	0.0401 (16)	0.0292 (16)	0.0198 (14)	0.0044 (12)	0.0202 (13)
C8	0.0349 (14)	0.0287 (13)	0.0258 (15)	0.0176 (13)	0.0025 (11)	0.0128 (11)
C9	0.0213 (11)	0.0208 (11)	0.0198 (13)	0.0098 (10)	0.0024 (9)	0.0089 (9)
C10	0.0249 (12)	0.0202 (11)	0.0182 (13)	0.0111 (10)	0.0026 (9)	0.0090 (9)
C11	0.0378 (15)	0.0224 (12)	0.0197 (14)	0.0154 (12)	0.0053 (11)	0.0088 (10)

Geometric parameters (Å, º) top

Cu—O2	1.9403 (19)	C5—C6	1.365 (4)
Cu—O4ⁱ	1.9463 (19)	C5—H5A	0.9300
Cu—OW2	1.999 (3)	C11—C10	1.511 (4)
Cu—N	2.096 (2)	C7—C8	1.362 (4)
Cu—OW1	2.320 (3)	C7—C6	1.403 (4)
O2—C11	1.264 (3)	C7—H7A	0.9300
OW2—H3	0.872 (18)	C10—C2	1.413 (4)
OW2—H4	0.888 (18)	C6—H6A	0.9300
N—C10	1.332 (3)	C8—H8A	0.9300
N—C9	1.367 (3)	OW3—H5	0.820 (19)
OW1—H1	0.813 (18)	OW3—H6	0.803 (18)
OW1—H2	0.810 (18)	C2—C3	1.365 (4)
O1—C11	1.231 (3)	C2—C1	1.517 (3)
C9—C8	1.416 (3)	C3—H3A	0.9300
C9—C4	1.430 (4)	C1—O3	1.234 (4)
C4—C3	1.403 (4)	C1—O4	1.270 (3)
C4—C5	1.418 (4)	O4—Cuⁱⁱ	1.9463 (19)

O2—Cu—O4ⁱ	175.29 (9)	C4—C5—H5A	119.8
O2—Cu—OW2	86.24 (10)	O1—C11—O2	125.0 (3)
O4ⁱ—Cu—OW2	89.79 (10)	O1—C11—C10	119.1 (2)
O2—Cu—N	81.69 (8)	O2—C11—C10	115.9 (2)
O4ⁱ—Cu—N	101.87 (8)	C8—C7—C6	120.8 (3)
OW2—Cu—N	165.40 (10)	C8—C7—H7A	119.6
O2—Cu—OW1	95.74 (10)	C6—C7—H7A	119.6
O4ⁱ—Cu—OW1	87.18 (9)	N—C10—C2	123.3 (2)
OW2—Cu—OW1	95.84 (12)	N—C10—C11	115.7 (2)
N—Cu—OW1	93.51 (10)	C2—C10—C11	120.9 (2)
C11—O2—Cu	116.02 (17)	C5—C6—C7	120.5 (3)
Cu—OW2—H3	117 (3)	C5—C6—H6A	119.7
Cu—OW2—H4	116 (3)	C7—C6—H6A	119.7
H3—OW2—H4	101 (2)	C7—C8—C9	120.8 (3)
C10—N—C9	119.2 (2)	C7—C8—H8A	119.6
C10—N—Cu	108.84 (17)	C9—C8—H8A	119.6
C9—N—Cu	131.95 (17)	H5—OW3—H6	112 (3)
Cu—OW1—H1	112 (3)	C3—C2—C10	118.0 (2)
Cu—OW1—H2	113 (3)	C3—C2—C1	119.3 (2)
H1—OW1—H2	111 (3)	C10—C2—C1	122.7 (2)
N—C9—C8	120.9 (2)	C2—C3—C4	120.7 (2)
N—C9—C4	120.7 (2)	C2—C3—H3A	119.6
C8—C9—C4	118.4 (2)	C4—C3—H3A	119.6
C3—C4—C5	122.9 (2)	O3—C1—O4	127.4 (2)
C3—C4—C9	118.0 (2)	O3—C1—C2	118.7 (2)
C5—C4—C9	119.1 (2)	O4—C1—C2	113.6 (2)
C6—C5—C4	120.3 (3)	C1—O4—Cuⁱⁱ	127.31 (19)
C6—C5—H5A	119.8

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
OW1—H1···OW3ⁱⁱⁱ	0.81 (2)	2.11 (2)	2.916 (4)	177 (4)
OW1—H2···O3ⁱⁱⁱ	0.81 (2)	2.15 (2)	2.944 (3)	166 (5)
OW2—H3···O1ⁱ	0.87 (2)	2.12 (2)	2.962 (3)	163 (4)
OW2—H4···O2^iv	0.89 (2)	2.29 (2)	3.174 (3)	178 (4)
OW3—H5···O1^v	0.82 (2)	1.96 (2)	2.775 (4)	170 (5)
OW3—H6···O3ⁱ	0.80 (2)	2.12 (2)	2.909 (3)	169 (5)

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

Experimental details

Crystal data
Chemical formula	[Cu(C₁₁H₅NO₄)(H₂O)₂]·H₂O
M_r	332.76
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.0284 (14), 7.5836 (15), 13.276 (3)
α, β, γ (°)	104.74 (3), 91.19 (3), 116.03 (3)
V (Å³)	607.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.83
Crystal size (mm)	0.43 × 0.34 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.763, 0.854
No. of measured, independent and observed [I > 2σ(I)] reflections	5813, 2696, 2382
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.10
No. of reflections	2696
No. of parameters	199
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.74

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), 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
OW1—H1···OW3ⁱ	0.813 (18)	2.105 (19)	2.916 (4)	177 (4)
OW1—H2···O3ⁱ	0.810 (18)	2.15 (2)	2.944 (3)	166 (5)
OW2—H3···O1ⁱⁱ	0.872 (18)	2.117 (19)	2.962 (3)	163 (4)
OW2—H4···O2ⁱⁱⁱ	0.888 (18)	2.287 (19)	3.174 (3)	178 (4)
OW3—H5···O1^iv	0.820 (19)	1.96 (2)	2.775 (4)	170 (5)
OW3—H6···O3ⁱⁱ	0.803 (18)	2.12 (2)	2.909 (3)	169 (5)

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

Acknowledgements

This work was supported by the National Natural Science (No.21207117) and Zhejiang Provincial Municipal Science and Technology Project (2008 C12055).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Li, X. & Liu, G. (2010). Z. Kristallogr. New Cryst. Struct. 225, 761–762. CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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