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

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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'

Crystal data

[Cu(C10H8N2)2(H2O)4](C12H6O4)·3H2O	F(000) = 1492
Mr = 716.19	Dx = 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) Å^3	Plate, blue
Z = 4	0.36 × 0.10 × 0.06 mm

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0734P)^2] where P = (Fo^2 + 2Fc^2)/3
3768 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.67 e Å^−3
7 restraints	Δρmin = −0.52 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cu1—O1w	2.385 (3)	C12—C13	1.434 (3)
Cu1—O2w	2.005 (2)	C13—C14^ii	1.406 (3)
Cu1—O2w^i	2.005 (2)	C13—C13^ii	1.425 (4)
Cu1—O3w	2.457 (3)	C14—C15	1.363 (3)
Cu1—N1	2.079 (2)	C14—C13^ii	1.406 (3)
Cu1—N1^i	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	C14^ii—C13—C13^ii	119.6 (2)
O1w—Cu1—O2w	88.8 (1)	C14^ii—C13—C12	122.9 (2)
O1w—Cu1—O2w^i	88.8 (1)	C13^ii—C13—C12	117.5 (2)
O1w—Cu1—N1	91.6 (1)	C15—C14—C13^ii	120.8 (2)
O1w—Cu1—N1^i	91.6 (1)	C14—C15—C11	121.0 (2)
O2w—Cu1—O2w^i	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—N1^i	91.1 (1)	Cu1—O1w—H1w1	122
O2w^i—Cu1—O3w	91.2 (1)	Cu1—O2w—H2w1	116
O2w^i—Cu1—N1	91.1 (1)	Cu1—O2w—H2w2	119
O2w^i—Cu1—N1^i	89.0 (1)	H2w1—O2w—H2w2	123
O3w—Cu1—N1	88.4 (1)	Cu1—O3w—H3w1	126
O3w—Cu1—N1^i	88.4 (1)	H4w1—O4w—H4w2	112
N1—Cu1—N1^i	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)	C13^ii—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)
O2w^i—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)
O2w^i—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—C14^ii	−178.5 (2)
C1—C2—C3—C8	−179.6 (2)	C11—C12—C13—C13^ii	1.0 (3)
C2—C3—C4—C5	−1.4 (3)	C13^ii—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)

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O4w^i	0.84	1.92	2.738 (3)	165
O2w—H2w1···N2^iii	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.