Tetra­aqua­bis(4,4′-bi­pyridine)copper(II) 2,6-naphthalene­di­carboxyl­ate trihydrate

Tao, J.; Huang, R.-B.; Zheng, L.-S.; Ng, S.W.

doi:10.1107/S1600536803015290

Tetraaquabis(4,4'-bipyridine)copper(II) 2,6-naphthalenedicarboxylate trihydrate

J. Tao, R.-B. Huang, L.-S. Zheng and S. W. Ng

The Cu atom in [Cu(C₁₀H₈N₂)₂(H₂O)₄](C₁₂H₆O₄)·3H₂O exists in a trans-N₂O₄ octahedral coordination polyhedron that is formed by the N atoms of two 4,4'-bipyridine heterocycles and the O atoms of four water molecules. The carboxylate groups of the centrosymmetric anions interact indirectly with the Cu atoms through the coordinated water molecules. The cations and anions are linked by hydrogen bonds into a network motif. The Cu atom lies at a site of 2 symmetry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015290/lh6079sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015290/lh6079Isup2.hkl Contains datablock I

CCDC reference: 221636

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.120
Data-to-parameter ratio = 15.7

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.30
         From the CIF: _reflns_number_total               3768
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3977
         Completeness (_total/calc)             94.74%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Triaquabis(4,4'-bipyridine)copper(II) 2,6-naphthalenedicarboxylate tetrahydrate' top

Crystal data top

[Cu(C₁₀H₈N₂)₂(H₂O)₄](C₁₂H₆O₄)·3H₂O	F(000) = 1492
M_r = 716.19	D_x = 1.49 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2701 reflections
a = 7.4063 (5) Å	θ = 2.8–24.7°
b = 18.157 (1) Å	µ = 0.75 mm⁻¹
c = 23.801 (2) Å	T = 298 K
V = 3200.7 (4) Å³	Plate, blue
Z = 4	0.36 × 0.10 × 0.06 mm

Data collection top

Bruker AXS area-detector diffractometer	3768 independent reflections
Radiation source: fine-focus sealed tube	2292 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.677, T_max = 0.914	k = −24→17
17912 measured reflections	l = −30→31

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0734P)²] where P = (F_o² + 2F_c²)/3
3768 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.67 e Å⁻³
7 restraints	Δρ_min = −0.52 e Å⁻³

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

	x	y	z	U_iso*/U_eq
Cu1	0.5000	0.24374 (2)	0.2500	0.0310 (1)
O1	−0.0315 (2)	−0.0050 (1)	0.1277 (1)	0.0501 (5)
O2	−0.2467 (2)	−0.0395 (1)	0.1861 (1)	0.0590 (5)
O1w	0.5000	0.1124 (2)	0.2500	0.0620 (8)
O2w	0.7707 (3)	0.2414 (1)	0.2496 (1)	0.0623 (6)
O3w	0.5000	0.3790 (1)	0.2500	0.0464 (6)
O4w	0.1802 (4)	0.0533 (2)	0.2139 (1)	0.103 (1)
O5w	−0.5000	−0.1164 (2)	0.2500	0.079 (1)
N1	0.5065 (2)	0.2469 (1)	0.3373 (1)	0.0315 (4)
N2	0.5049 (3)	0.2676 (1)	0.6348 (1)	0.0463 (6)
C1	0.5615 (4)	0.3073 (1)	0.3648 (1)	0.0380 (6)
C2	0.5619 (4)	0.3127 (1)	0.4223 (1)	0.0373 (6)
C3	0.5073 (3)	0.2537 (1)	0.4553 (1)	0.0301 (5)
C4	0.4542 (3)	0.1903 (1)	0.4265 (1)	0.0338 (5)
C5	0.4542 (3)	0.1895 (1)	0.3691 (1)	0.0354 (6)
C6	0.4624 (4)	0.3252 (1)	0.6023 (1)	0.0482 (7)
C7	0.4614 (3)	0.3233 (1)	0.5446 (1)	0.0398 (6)
C8	0.5051 (3)	0.2582 (1)	0.5169 (1)	0.0303 (5)
C9	0.5471 (3)	0.1982 (1)	0.5509 (1)	0.0357 (6)
C10	0.5470 (4)	0.2058 (1)	0.6080 (1)	0.0435 (6)
C11	−0.3317 (3)	−0.0108 (1)	0.0924 (1)	0.0324 (5)
C12	−0.2785 (3)	−0.0043 (1)	0.0378 (1)	0.0336 (5)
C13	−0.4066 (3)	0.0005 (1)	−0.0072 (1)	0.0311 (5)
C14	−0.6447 (3)	−0.0055 (1)	0.0639 (1)	0.0353 (5)
C15	−0.5181 (3)	−0.0111 (1)	0.1053 (1)	0.0360 (5)
C16	−0.1917 (3)	−0.0182 (1)	0.1388 (1)	0.0345 (5)
H1w1	0.586	0.088	0.263	0.074*
H2w1	0.821	0.234	0.217	0.075*
H2w2	0.827	0.235	0.281	0.075*
H3w1	0.572	0.407	0.232	0.056*
H4w1	0.126	0.030	0.188	0.123*
H4w2	0.164	0.033	0.246	0.123*
H5w1	−0.425	−0.092	0.230	0.095*
H1	0.6014	0.3474	0.3439	0.046*
H2	0.5989	0.3563	0.4393	0.045*
H4	0.4188	0.1487	0.4464	0.041*
H5	0.4159	0.1469	0.3510	0.043*
H6	0.4317	0.3692	0.6199	0.058*
H7	0.4318	0.3653	0.5242	0.048*
H9	0.5751	0.1530	0.5347	0.043*
H10	0.5785	0.1650	0.6296	0.052*
H12	−0.1558	−0.0030	0.0295	0.040*
H14	−0.7665	−0.0050	0.0734	0.042*
H15	−0.5548	−0.0153	0.1425	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0275 (2)	0.0451 (3)	0.0206 (2)	0.000	−0.0001 (2)	0.000
O1	0.035 (1)	0.072 (1)	0.044 (1)	−0.008 (1)	−0.005 (1)	0.007 (1)
O2	0.044 (1)	0.099 (2)	0.034 (1)	−0.008 (1)	−0.004 (1)	0.016 (1)
O1w	0.078 (2)	0.047 (2)	0.061 (2)	0.000	−0.009 (2)	0.000
O2w	0.043 (1)	0.106 (2)	0.038 (1)	0.001 (1)	−0.001 (1)	−0.002 (1)
O3w	0.060 (2)	0.043 (1)	0.036 (1)	0.000	0.014 (1)	0.000
O4w	0.110 (2)	0.142 (3)	0.056 (2)	−0.064 (2)	−0.021 (2)	0.019 (2)
O5w	0.076 (2)	0.056 (2)	0.106 (3)	0.000	0.042 (2)	0.000
N1	0.031 (1)	0.038 (1)	0.026 (1)	−0.002 (1)	−0.001 (1)	0.002 (1)
N2	0.063 (2)	0.048 (1)	0.027 (1)	−0.002 (1)	−0.001 (1)	−0.002 (1)
C1	0.046 (2)	0.038 (1)	0.030 (1)	−0.007 (1)	−0.001 (1)	0.006 (1)
C2	0.049 (2)	0.032 (1)	0.030 (1)	−0.007 (1)	−0.003 (1)	0.001 (1)
C3	0.030 (1)	0.034 (1)	0.027 (1)	0.002 (1)	−0.002 (1)	0.002 (1)
C4	0.043 (2)	0.029 (1)	0.029 (1)	−0.004 (1)	0.000 (1)	0.004 (1)
C5	0.043 (2)	0.032 (1)	0.031 (1)	−0.004 (1)	−0.004 (1)	−0.002 (1)
C6	0.067 (2)	0.041 (1)	0.036 (1)	0.005 (1)	0.001 (1)	−0.010 (1)
C7	0.054 (2)	0.035 (1)	0.031 (1)	0.005 (1)	0.000 (1)	−0.001 (1)
C8	0.031 (1)	0.033 (1)	0.027 (1)	−0.002 (1)	0.000 (1)	0.000 (1)
C9	0.045 (2)	0.032 (1)	0.031 (1)	0.001 (1)	−0.001 (1)	0.001 (1)
C10	0.059 (2)	0.041 (1)	0.031 (1)	−0.002 (1)	−0.004 (1)	0.009 (1)
C11	0.037 (1)	0.026 (1)	0.034 (1)	−0.001 (1)	−0.003 (1)	−0.001 (1)
C12	0.035 (1)	0.029 (1)	0.037 (1)	0.000 (1)	−0.002 (1)	0.001 (1)
C13	0.032 (1)	0.025 (1)	0.036 (1)	0.000 (1)	0.001 (1)	0.001 (1)
C14	0.033 (1)	0.038 (1)	0.035 (1)	0.001 (1)	0.003 (1)	0.001 (1)
C15	0.040 (2)	0.038 (1)	0.030 (1)	0.000 (1)	0.002 (1)	0.001 (1)
C16	0.038 (2)	0.035 (1)	0.031 (1)	−0.001 (1)	−0.003 (1)	−0.001 (1)

Geometric parameters (Å, º) top

Cu1—O1w	2.385 (3)	C12—C13	1.434 (3)
Cu1—O2w	2.005 (2)	C13—C14ⁱⁱ	1.406 (3)
Cu1—O2wⁱ	2.005 (2)	C13—C13ⁱⁱ	1.425 (4)
Cu1—O3w	2.457 (3)	C14—C15	1.363 (3)
Cu1—N1	2.079 (2)	C14—C13ⁱⁱ	1.406 (3)
Cu1—N1ⁱ	2.079 (2)	O1w—H1w1	0.84
O1—C16	1.239 (3)	O2w—H2w1	0.87
O2—C16	1.259 (3)	O2w—H2w2	0.86
N1—C1	1.341 (3)	O3w—H3w1	0.85
N1—C5	1.345 (3)	O4w—H4w1	0.85
N2—C10	1.327 (3)	O4w—H4w2	0.85
N2—C6	1.339 (3)	O5w—H5w1	0.85
C1—C2	1.372 (3)	C1—H1	0.93
C2—C3	1.388 (3)	C2—H2	0.93
C3—C4	1.396 (3)	C4—H4	0.93
C3—C8	1.470 (3)	C5—H5	0.93
C4—C5	1.366 (3)	C6—H6	0.93
C6—C7	1.375 (3)	C7—H7	0.93
C7—C8	1.392 (3)	C9—H9	0.93
C8—C9	1.392 (3)	C10—H10	0.93
C9—C10	1.367 (3)	C12—H12	0.93
C11—C12	1.362 (3)	C14—H14	0.93
C11—C15	1.414 (3)	C15—H15	0.93
C11—C16	1.520 (3)

O1w—Cu1—O3w	180.0	C14ⁱⁱ—C13—C13ⁱⁱ	119.6 (2)
O1w—Cu1—O2w	88.8 (1)	C14ⁱⁱ—C13—C12	122.9 (2)
O1w—Cu1—O2wⁱ	88.8 (1)	C13ⁱⁱ—C13—C12	117.5 (2)
O1w—Cu1—N1	91.6 (1)	C15—C14—C13ⁱⁱ	120.8 (2)
O1w—Cu1—N1ⁱ	91.6 (1)	C14—C15—C11	121.0 (2)
O2w—Cu1—O2wⁱ	177.6 (1)	O1—C16—O2	124.0 (2)
O2w—Cu1—O3w	91.2 (1)	O1—C16—C11	118.8 (2)
O2w—Cu1—N1	89.0 (1)	O2—C16—C11	117.2 (2)
O2w—Cu1—N1ⁱ	91.1 (1)	Cu1—O1w—H1w1	122
O2wⁱ—Cu1—O3w	91.2 (1)	Cu1—O2w—H2w1	116
O2wⁱ—Cu1—N1	91.1 (1)	Cu1—O2w—H2w2	119
O2wⁱ—Cu1—N1ⁱ	89.0 (1)	H2w1—O2w—H2w2	123
O3w—Cu1—N1	88.4 (1)	Cu1—O3w—H3w1	126
O3w—Cu1—N1ⁱ	88.4 (1)	H4w1—O4w—H4w2	112
N1—Cu1—N1ⁱ	176.9 (1)	N1—C1—H1	118.4
C1—N1—C5	116.5 (2)	C2—C1—H1	118.4
C1—N1—Cu1	121.2 (1)	C1—C2—H2	119.7
C5—N1—Cu1	122.4 (2)	C3—C2—H2	119.7
C10—N2—C6	116.0 (2)	C5—C4—H4	120.0
N1—C1—C2	123.1 (2)	C3—C4—H4	120.0
C1—C2—C3	120.5 (2)	N1—C5—H5	118.1
C2—C3—C4	116.2 (2)	C4—C5—H5	118.1
C2—C3—C8	121.7 (2)	N2—C6—H6	118.0
C4—C3—C8	122.1 (2)	C7—C6—H6	118.0
C5—C4—C3	119.9 (2)	C6—C7—H7	120.2
N1—C5—C4	123.7 (2)	C8—C7—H7	120.2
N2—C6—C7	124.0 (2)	C10—C9—H9	120.0
C6—C7—C8	119.5 (2)	C8—C9—H9	120.0
C9—C8—C7	116.2 (2)	N2—C10—H10	117.9
C9—C8—C3	122.3 (2)	C9—C10—H10	117.9
C7—C8—C3	121.4 (2)	C11—C12—H12	119.1
C10—C9—C8	119.9 (2)	C13—C12—H12	119.1
N2—C10—C9	124.3 (2)	C15—C14—H14	119.6
C12—C11—C15	119.3 (2)	C13ⁱⁱ—C14—H14	119.6
C12—C11—C16	120.2 (2)	C14—C15—H15	119.5
C15—C11—C16	120.5 (2)	C11—C15—H15	119.5
C11—C12—C13	121.8 (2)

O2w—Cu1—N1—C1	71.2 (2)	C6—C7—C8—C3	−179.5 (2)
O2wⁱ—Cu1—N1—C1	−111.2 (2)	C2—C3—C8—C9	−144.7 (2)
O1w—Cu1—N1—C1	160.0 (2)	C4—C3—C8—C9	35.6 (3)
O3w—Cu1—N1—C1	−20.0 (2)	C2—C3—C8—C7	35.0 (3)
O2w—Cu1—N1—C5	−109.7 (2)	C4—C3—C8—C7	−144.7 (2)
O2wⁱ—Cu1—N1—C5	68.0 (2)	C7—C8—C9—C10	−1.2 (3)
O1w—Cu1—N1—C5	−20.9 (2)	C3—C8—C9—C10	178.5 (2)
O3w—Cu1—N1—C5	159.1 (2)	C6—N2—C10—C9	−0.8 (4)
C5—N1—C1—C2	−1.6 (3)	C8—C9—C10—N2	1.6 (4)
Cu1—N1—C1—C2	177.6 (2)	C15—C11—C12—C13	−1.4 (3)
N1—C1—C2—C3	1.4 (4)	C16—C11—C12—C13	178.0 (2)
C1—C2—C3—C4	0.2 (3)	C11—C12—C13—C14ⁱⁱ	−178.5 (2)
C1—C2—C3—C8	−179.6 (2)	C11—C12—C13—C13ⁱⁱ	1.0 (3)
C2—C3—C4—C5	−1.4 (3)	C13ⁱⁱ—C14—C15—C11	1.2 (3)
C8—C3—C4—C5	178.3 (2)	C12—C11—C15—C14	0.3 (3)
C1—N1—C5—C4	0.2 (3)	C16—C11—C15—C14	−179.1 (2)
Cu1—N1—C5—C4	−178.9 (2)	C12—C11—C16—O1	13.0 (3)
C3—C4—C5—N1	1.3 (4)	C15—C11—C16—O1	−167.6 (2)
C10—N2—C6—C7	−0.3 (4)	C12—C11—C16—O2	−165.3 (2)
N2—C6—C7—C8	0.6 (4)	C15—C11—C16—O2	14.1 (3)
C6—C7—C8—C9	0.2 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O4wⁱ	0.84	1.92	2.738 (3)	165
O2w—H2w1···N2ⁱⁱⁱ	0.87	2.34	3.202 (3)	169
O2w—H2w2···N2^iv	0.86	2.40	3.257 (3)	173
O3w—H3w1···O2^v	0.85	1.96	2.799 (2)	174
O4w—H4w1···O1	0.85	1.95	2.792 (3)	168
O4w—H4w2···O2^vi	0.85	2.17	2.955 (3)	153
O5w—H5w1···O2	0.85	1.94	2.790 (2)	177

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

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Tetra­aqua­bis(4,4'-bi­pyridine)copper(II) 2,6-naphthalene­di­carboxyl­ate trihydrate

Supporting information

Key indicators

checkCIF results

Tetraaquabis(4,4'-bipyridine)copper(II) 2,6-naphthalenedicarboxylate trihydrate