catena-Poly[[[aqua-(5-carb-oxy-pyridine-3-carboxyl-ato-κN)copper(I)]-μ-4,4'-bipyridine-κN:N'] monohydrate].

In the title compound, {[Cu(C(7)H(4)NO(4))(C(10)H(8)N(2))(H(2)O)]·H(2)O}(n), the Cu(I) ion is coordinated by the N atom from a 5-carb-oxy-pyridine-3-carboxyl-ate anion, two N atoms from two 4,4'-bipyridine (4,4'-bipy) ligands and one water mol-ecule in a distorted tetra-hedral geometry. The 4,4'-bipy ligands bridge the Cu(I) ions into polymeric chains propagating in [201]. The latticeand the coordinating water mol-ecules as well as the carboxy OH function are involved in the formation of inter-molecular O-H⋯O hydrogen bonds, which consolidate the crystal packing.

Related literature

For related structures of derivatives of pyridine-3,5-dicarb­oxy­lic acid in coordination chemistry, see: Qin et al. (2002 ▶); Eubank et al. (2007 ▶); Mirtschin et al. (2008 ▶); Banerjee et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

[Cu(C7H4NO4)(C10H8N2)(H2O)]·H2O

M = 421.87

Monoclinic,

a = 10.6511 (13) Å

b = 23.321 (3) Å

c = 7.0111 (8) Å

β = 105.044 (7)°

V = 1681.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.34 mm−1

T = 298 K

0.30 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.689, T max = 0.856

13086 measured reflections

2971 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.127

S = 1.03

2971 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055656/cv5224sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055656/cv5224Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C7H4NO4)(C10H8N2)(H2O)]·H2O	F(000) = 864
Mr = 421.87	Dx = 1.666 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4034 reflections
a = 10.6511 (13) Å	θ = 2.6–26.3°
b = 23.321 (3) Å	µ = 1.34 mm−1
c = 7.0111 (8) Å	T = 298 K
β = 105.044 (7)°	Block, yellow
V = 1681.9 (3) Å3	0.30 × 0.20 × 0.12 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2971 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→11
Tmin = 0.689, Tmax = 0.856	k = −27→27
13086 measured reflections	l = −8→8

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0881P)2 + 0.020P] where P = (Fo2 + 2Fc2)/3
2971 reflections	(Δ/σ)max = 0.001
245 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cu1	1.25554 (4)	0.334248 (14)	0.91097 (6)	0.03596 (18)
N2	1.0793 (3)	0.30297 (10)	0.7883 (4)	0.0331 (6)
O1	0.8837 (2)	0.42750 (9)	1.2312 (4)	0.0429 (6)
H1A	0.8138	0.4356	1.2531	0.064*
O6	0.3423 (2)	0.55931 (9)	0.7333 (4)	0.0423 (6)
H5WA	1.3391	0.4178	0.6721	0.063*
H5WB	1.2197	0.4224	0.6553	0.063*
N1	1.2308 (2)	0.40329 (10)	1.0943 (4)	0.0329 (6)
O3	1.5049 (2)	0.53445 (8)	1.2189 (4)	0.0404 (6)
O2	0.9233 (2)	0.52059 (8)	1.2933 (3)	0.0372 (5)
O4	1.3867 (2)	0.58268 (9)	1.3819 (4)	0.0455 (6)
C8	1.0490 (3)	0.24710 (12)	0.7920 (5)	0.0347 (7)
H8	1.1159	0.2213	0.8425	0.042*
C10	0.8215 (3)	0.26339 (11)	0.6516 (4)	0.0267 (6)
C6	0.9569 (3)	0.47324 (12)	1.2534 (4)	0.0296 (7)
C16	0.5797 (3)	0.27900 (12)	0.5599 (4)	0.0308 (7)
H16	0.5926	0.3183	0.5789	0.037*
O5	1.2742 (2)	0.39559 (9)	0.6563 (4)	0.0489 (6)
H6WA	0.3745	0.5267	0.7734	0.073*
H6WB	0.3550	0.5631	0.6190	0.073*
C3	1.1825 (3)	0.50477 (11)	1.2678 (4)	0.0284 (7)
H3	1.1658	0.5389	1.3253	0.034*
C2	1.0874 (3)	0.46268 (11)	1.2204 (4)	0.0276 (6)
C4	1.3011 (3)	0.49604 (11)	1.2300 (4)	0.0295 (7)
C11	0.8532 (3)	0.32095 (12)	0.6460 (5)	0.0341 (7)
H11	0.7882	0.3477	0.5968	0.041*
C9	0.9247 (3)	0.22588 (12)	0.7254 (4)	0.0314 (7)
H9	0.9095	0.1867	0.7295	0.038*
C13	0.6855 (3)	0.24224 (11)	0.5851 (4)	0.0269 (6)
C7	1.4074 (3)	0.54121 (11)	1.2813 (5)	0.0311 (7)
C14	0.6585 (3)	0.18475 (12)	0.5473 (5)	0.0312 (7)
H14	0.7261	0.1586	0.5593	0.037*
C12	0.9796 (3)	0.33862 (12)	0.7125 (5)	0.0366 (8)
H12	0.9975	0.3775	0.7049	0.044*
C5	1.3199 (3)	0.44466 (12)	1.1400 (5)	0.0338 (7)
H5	1.3991	0.4389	1.1101	0.041*
C1	1.1176 (3)	0.41237 (12)	1.1376 (4)	0.0306 (7)
H1	1.0556	0.3833	1.1106	0.037*
C17	0.4562 (3)	0.25688 (12)	0.5068 (5)	0.0337 (7)
H17	0.3866	0.2820	0.4929	0.040*
N3	0.4300 (2)	0.20061 (10)	0.4737 (4)	0.0304 (6)
C15	0.5326 (3)	0.16626 (11)	0.4921 (5)	0.0334 (7)
H15	0.5175	0.1274	0.4659	0.040*

	U11	U22	U33	U12	U13	U23
Cu1	0.0197 (3)	0.0308 (3)	0.0561 (3)	0.00068 (14)	0.0077 (2)	−0.00424 (16)
N2	0.0244 (15)	0.0280 (12)	0.0466 (15)	−0.0045 (11)	0.0086 (12)	−0.0057 (11)
O1	0.0288 (14)	0.0324 (11)	0.0746 (16)	−0.0040 (10)	0.0262 (13)	−0.0099 (11)
O6	0.0284 (14)	0.0416 (12)	0.0603 (15)	0.0022 (10)	0.0178 (11)	−0.0056 (11)
N1	0.0236 (15)	0.0269 (12)	0.0500 (16)	−0.0006 (10)	0.0130 (13)	−0.0076 (10)
O3	0.0279 (13)	0.0320 (11)	0.0676 (16)	−0.0059 (9)	0.0235 (12)	−0.0052 (10)
O2	0.0320 (13)	0.0281 (11)	0.0554 (14)	0.0056 (9)	0.0184 (11)	−0.0027 (9)
O4	0.0433 (15)	0.0270 (11)	0.0730 (16)	−0.0090 (10)	0.0275 (13)	−0.0154 (11)
C8	0.0261 (19)	0.0266 (14)	0.0503 (19)	0.0014 (13)	0.0081 (15)	−0.0025 (13)
C10	0.0253 (18)	0.0255 (13)	0.0311 (15)	−0.0036 (12)	0.0103 (13)	−0.0030 (11)
C6	0.0250 (17)	0.0289 (14)	0.0357 (16)	0.0007 (12)	0.0090 (13)	0.0027 (12)
C16	0.0269 (18)	0.0219 (13)	0.0443 (17)	−0.0018 (12)	0.0109 (14)	−0.0043 (12)
O5	0.0370 (15)	0.0440 (13)	0.0656 (16)	−0.0032 (11)	0.0133 (12)	0.0091 (11)
C3	0.0277 (17)	0.0222 (13)	0.0359 (16)	0.0019 (12)	0.0092 (14)	−0.0021 (11)
C2	0.0255 (17)	0.0247 (13)	0.0344 (15)	0.0016 (12)	0.0109 (13)	0.0021 (11)
C4	0.0255 (18)	0.0237 (13)	0.0414 (17)	−0.0009 (12)	0.0125 (14)	0.0017 (12)
C11	0.0249 (18)	0.0242 (13)	0.0525 (19)	0.0017 (13)	0.0087 (15)	−0.0008 (13)
C9	0.0273 (18)	0.0225 (13)	0.0453 (17)	−0.0029 (12)	0.0113 (14)	−0.0013 (12)
C13	0.0234 (17)	0.0285 (14)	0.0287 (14)	−0.0037 (12)	0.0065 (12)	0.0001 (11)
C7	0.0274 (18)	0.0204 (13)	0.0451 (18)	−0.0005 (12)	0.0086 (15)	0.0046 (12)
C14	0.0209 (17)	0.0245 (13)	0.0472 (18)	0.0003 (12)	0.0070 (14)	−0.0010 (13)
C12	0.0254 (19)	0.0245 (14)	0.058 (2)	−0.0048 (12)	0.0071 (16)	−0.0021 (13)
C5	0.0257 (18)	0.0311 (15)	0.0477 (19)	0.0005 (13)	0.0151 (15)	−0.0070 (13)
C1	0.0258 (17)	0.0275 (14)	0.0387 (16)	−0.0029 (13)	0.0090 (14)	−0.0026 (12)
C17	0.0259 (18)	0.0246 (13)	0.0502 (19)	0.0005 (13)	0.0090 (15)	−0.0020 (13)
N3	0.0214 (14)	0.0297 (12)	0.0389 (14)	−0.0037 (11)	0.0059 (11)	0.0004 (10)
C15	0.0285 (19)	0.0228 (14)	0.0484 (19)	−0.0028 (12)	0.0094 (15)	−0.0008 (12)

Cu1—N3i	1.971 (2)	C16—H16	0.9300
Cu1—N2	1.989 (3)	O5—H5WA	0.8480
Cu1—N1	2.119 (2)	O5—H5WB	0.8518
Cu1—O5	2.336 (2)	C3—C4	1.372 (4)
N2—C8	1.344 (4)	C3—C2	1.387 (4)
N2—C12	1.345 (4)	C3—H3	0.9300
O1—C6	1.307 (3)	C2—C1	1.383 (4)
O1—H1A	0.8200	C4—C5	1.393 (4)
O6—H6WA	0.8511	C4—C7	1.520 (4)
O6—H6WB	0.8511	C11—C12	1.369 (5)
N1—C5	1.333 (4)	C11—H11	0.9300
N1—C1	1.334 (4)	C9—H9	0.9300
O3—C7	1.237 (4)	C13—C14	1.383 (4)
O2—C6	1.216 (3)	C14—C15	1.365 (4)
O4—C7	1.250 (4)	C14—H14	0.9300
C8—C9	1.377 (4)	C12—H12	0.9300
C8—H8	0.9300	C5—H5	0.9300
C10—C11	1.387 (4)	C1—H1	0.9300
C10—C9	1.395 (4)	C17—N3	1.349 (4)
C10—C13	1.486 (4)	C17—H17	0.9300
C6—C2	1.488 (4)	N3—C15	1.334 (4)
C16—C17	1.372 (4)	N3—Cu1ii	1.971 (2)
C16—C13	1.390 (4)	C15—H15	0.9300
N3i—Cu1—N2	132.42 (10)	C3—C4—C7	121.2 (2)
N3i—Cu1—N1	115.90 (10)	C5—C4—C7	121.1 (3)
N2—Cu1—N1	106.79 (10)	C12—C11—C10	120.5 (3)
N3i—Cu1—O5	99.25 (9)	C12—C11—H11	119.8
N2—Cu1—O5	98.75 (10)	C10—C11—H11	119.8
N1—Cu1—O5	92.69 (9)	C8—C9—C10	119.7 (3)
C8—N2—C12	116.0 (3)	C8—C9—H9	120.1
C8—N2—Cu1	123.5 (2)	C10—C9—H9	120.1
C12—N2—Cu1	120.25 (19)	C14—C13—C16	116.9 (3)
C6—O1—H1A	109.5	C14—C13—C10	121.3 (3)
H6WA—O6—H6WB	104.8	C16—C13—C10	121.8 (2)
C5—N1—C1	117.4 (2)	O3—C7—O4	125.9 (3)
C5—N1—Cu1	120.2 (2)	O3—C7—C4	118.1 (3)
C1—N1—Cu1	121.37 (19)	O4—C7—C4	116.1 (3)
N2—C8—C9	123.8 (3)	C15—C14—C13	120.0 (3)
N2—C8—H8	118.1	C15—C14—H14	120.0
C9—C8—H8	118.1	C13—C14—H14	120.0
C11—C10—C9	116.3 (3)	N2—C12—C11	123.7 (3)
C11—C10—C13	122.5 (3)	N2—C12—H12	118.2
C9—C10—C13	121.2 (2)	C11—C12—H12	118.2
O2—C6—O1	124.5 (3)	N1—C5—C4	123.6 (3)
O2—C6—C2	122.0 (3)	N1—C5—H5	118.2
O1—C6—C2	113.6 (2)	C4—C5—H5	118.2
C17—C16—C13	119.4 (3)	N1—C1—C2	123.5 (3)
C17—C16—H16	120.3	N1—C1—H1	118.3
C13—C16—H16	120.3	C2—C1—H1	118.3
Cu1—O5—H5WA	120.2	N3—C17—C16	123.6 (3)
Cu1—O5—H5WB	105.2	N3—C17—H17	118.2
H5WA—O5—H5WB	94.7	C16—C17—H17	118.2
C4—C3—C2	120.0 (3)	C15—N3—C17	116.1 (3)
C4—C3—H3	120.0	C15—N3—Cu1ii	118.36 (19)
C2—C3—H3	120.0	C17—N3—Cu1ii	125.5 (2)
C1—C2—C3	117.8 (3)	N3—C15—C14	123.9 (3)
C1—C2—C6	122.2 (3)	N3—C15—H15	118.1
C3—C2—C6	119.9 (2)	C14—C15—H15	118.1
C3—C4—C5	117.6 (3)
N3i—Cu1—N2—C8	24.8 (3)	C17—C16—C13—C10	−177.1 (3)
N1—Cu1—N2—C8	−128.5 (3)	C11—C10—C13—C14	164.4 (3)
O5—Cu1—N2—C8	136.0 (3)	C9—C10—C13—C14	−16.3 (4)
N3i—Cu1—N2—C12	−161.7 (2)	C11—C10—C13—C16	−16.3 (5)
N1—Cu1—N2—C12	44.9 (3)	C9—C10—C13—C16	163.1 (3)
O5—Cu1—N2—C12	−50.6 (3)	C3—C4—C7—O3	−170.0 (3)
N3i—Cu1—N1—C5	45.4 (3)	C5—C4—C7—O3	9.0 (4)
N2—Cu1—N1—C5	−156.2 (2)	C3—C4—C7—O4	9.0 (4)
O5—Cu1—N1—C5	−56.3 (2)	C5—C4—C7—O4	−172.0 (3)
N3i—Cu1—N1—C1	−146.8 (2)	C16—C13—C14—C15	−1.4 (4)
N2—Cu1—N1—C1	11.6 (3)	C10—C13—C14—C15	178.0 (3)
O5—Cu1—N1—C1	111.6 (2)	C8—N2—C12—C11	1.5 (5)
C12—N2—C8—C9	−0.5 (5)	Cu1—N2—C12—C11	−172.4 (3)
Cu1—N2—C8—C9	173.2 (2)	C10—C11—C12—N2	−0.9 (5)
C4—C3—C2—C1	0.8 (4)	C1—N1—C5—C4	0.2 (4)
C4—C3—C2—C6	−177.3 (3)	Cu1—N1—C5—C4	168.5 (2)
O2—C6—C2—C1	−166.9 (3)	C3—C4—C5—N1	−1.9 (5)
O1—C6—C2—C1	11.8 (4)	C7—C4—C5—N1	179.0 (3)
O2—C6—C2—C3	11.2 (4)	C5—N1—C1—C2	2.2 (4)
O1—C6—C2—C3	−170.2 (3)	Cu1—N1—C1—C2	−166.0 (2)
C2—C3—C4—C5	1.3 (4)	C3—C2—C1—N1	−2.7 (4)
C2—C3—C4—C7	−179.7 (3)	C6—C2—C1—N1	175.4 (3)
C9—C10—C11—C12	−0.7 (5)	C13—C16—C17—N3	−1.1 (5)
C13—C10—C11—C12	178.7 (3)	C16—C17—N3—C15	−1.1 (5)
N2—C8—C9—C10	−1.1 (5)	C16—C17—N3—Cu1ii	176.6 (2)
C11—C10—C9—C8	1.6 (4)	C17—N3—C15—C14	2.1 (5)
C13—C10—C9—C8	−177.8 (3)	Cu1ii—N3—C15—C14	−175.7 (3)
C17—C16—C13—C14	2.3 (4)	C13—C14—C15—N3	−0.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6iii	0.82	1.69	2.502 (3)	168.
O5—H5WB···O2iv	0.85	2.12	2.959 (3)	167.
O6—H6WA···O3iv	0.85	1.91	2.694 (3)	152.
O5—H5WA···O3v	0.85	1.98	2.809 (3)	165.
O6—H6WB···O4vi	0.85	1.84	2.682 (3)	171.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O6i	0.82	1.69	2.502 (3)	168
O5—H5WB⋯O2ii	0.85	2.12	2.959 (3)	167
O6—H6WA⋯O3ii	0.85	1.91	2.694 (3)	152
O5—H5WA⋯O3iii	0.85	1.98	2.809 (3)	165
O6—H6WB⋯O4iv	0.85	1.84	2.682 (3)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .