A one-dimensional hydrogen-bonding chain of diacetatobis(3-hydroxy­pyridine)copper(II)

The asymmetric unit of the title complex, [Cu(C₂H₃O₂)₂(C₅H₅NO)₂], consists of two half-units of [Cu(ac)₂(3-PyOH)₂] (ac is acetate and 3-PyOH is 3-hydroxy­pyridine). The two molecules in the unit cell are held together via hydrogen bonds in a chain structure; the Cu...Cu separation is 5.482 (2) Å. The Cu^II atoms in the two neutral units lie on special positions with inversion symmetry, and both show elongated octahedral geometry, defined by four acetate O atoms and two endo-N atoms of two 3-PyOH ligands.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.108
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Cu1    -   O2      ..      11.54 su

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C10     ..       5.27 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cu1    -   O1      ..       5.79 su

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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.

diacetatobis(3-hydroxypyridine)copper(II)

Crystal data

[Cu(C2H3O2)2(C5H5NO)2]	Z = 2
Mr = 371.83	F(000) = 382
Triclinic, P1	Dx = 1.546 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9725 (18) Å	Cell parameters from 7857 reflections
b = 10.138 (2) Å	θ = 3.4–27.5°
c = 10.247 (2) Å	µ = 1.40 mm^−1
α = 114.92 (3)°	T = 293 K
β = 100.20 (3)°	Prism, blue
γ = 100.07 (3)°	0.39 × 0.28 × 0.18 mm
V = 798.8 (4) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	3601 independent reflections
Radiation source: fine-focus sealed tube	2890 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 10 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −11→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→13
Tmin = 0.631, Tmax = 0.778	l = −12→13
7445 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 0.1657P] where P = (Fo^2 + 2Fc^2)/3
3601 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.53 e Å^−3
2 restraints	Δρmin = −0.42 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.0000	0.0000	0.0000	0.0347 (1)
Cu2	0.0000	0.5000	0.5000	0.0347 (1)
O1	0.1748 (2)	−0.0948 (2)	−0.0258 (2)	0.0434 (4)
O2	0.2423 (2)	0.0609 (2)	0.2163 (2)	0.0532 (5)
O3	0.1855 (3)	0.5584 (2)	0.0742 (2)	0.0512 (5)
H15	0.156 (4)	0.571 (4)	0.152 (3)	0.077*
O4	0.0856 (2)	0.7116 (2)	0.5423 (2)	0.0407 (4)
O5	0.0886 (2)	0.5812 (2)	0.3087 (2)	0.0492 (4)
O6	0.4440 (2)	0.2151 (2)	0.4832 (2)	0.0585 (5)
H16	0.380 (4)	0.157 (4)	0.397 (2)	0.088*
N1	0.1058 (2)	0.1543 (2)	−0.0518 (2)	0.0363 (4)
N2	0.2198 (2)	0.4905 (2)	0.5722 (2)	0.0379 (4)
C1	0.4120 (4)	−0.0927 (4)	0.1238 (4)	0.0602 (8)
H1A	0.4778	−0.0332	0.2251	0.090*
H1B	0.4698	−0.0832	0.0563	0.090*
H1C	0.3798	−0.1971	0.1016	0.090*
C2	0.2685 (3)	−0.0372 (3)	0.1053 (3)	0.0418 (6)
C3	0.1072 (3)	0.2990 (3)	0.0243 (3)	0.0377 (5)
H3	0.0571	0.3254	0.0999	0.045*
C4	0.1806 (3)	0.4115 (3)	−0.0055 (3)	0.0386 (5)
C5	0.2525 (4)	0.3710 (3)	−0.1190 (3)	0.0503 (6)
H5	0.3024	0.4436	−0.1418	0.060*
C6	0.2497 (4)	0.2205 (3)	−0.1989 (3)	0.0536 (7)
H6	0.2973	0.1910	−0.2763	0.064*
C7	0.1755 (3)	0.1151 (3)	−0.1622 (3)	0.0459 (6)
H7	0.1739	0.0143	−0.2157	0.055*
C8	0.1823 (4)	0.8520 (3)	0.4233 (4)	0.0587 (8)
H8A	0.2948	0.8718	0.4431	0.088*
H8B	0.1574	0.9327	0.5000	0.088*
H8C	0.1383	0.8453	0.3275	0.088*
C9	0.1141 (3)	0.7044 (3)	0.4223 (3)	0.0391 (5)
C10	0.2582 (3)	0.3611 (3)	0.5050 (3)	0.0398 (5)
H10	0.1825	0.2779	0.4249	0.048*
C11	0.4070 (3)	0.3470 (3)	0.5509 (3)	0.0415 (5)
C12	0.5187 (3)	0.4709 (3)	0.6690 (3)	0.0476 (6)
H12	0.6197	0.4651	0.7019	0.057*
C13	0.4784 (3)	0.6037 (3)	0.7376 (3)	0.0479 (6)
H13	0.5523	0.6883	0.8178	0.058*
C14	0.3284 (3)	0.6108 (3)	0.6872 (3)	0.0447 (6)
H14	0.3022	0.7009	0.7339	0.054*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0386 (2)	0.0294 (2)	0.0351 (2)	0.0091 (2)	0.0102 (2)	0.0145 (2)
Cu2	0.0364 (2)	0.0328 (2)	0.0343 (2)	0.0106 (2)	0.0099 (2)	0.0149 (2)
O1	0.0448 (9)	0.0421 (9)	0.046 (1)	0.0138 (8)	0.0119 (8)	0.0220 (8)
O2	0.052 (1)	0.047 (1)	0.049 (1)	0.0191 (9)	0.0102 (9)	0.0121 (9)
O3	0.069 (1)	0.0343 (9)	0.051 (1)	0.0119 (9)	0.020 (1)	0.0206 (9)
O4	0.0426 (9)	0.0372 (9)	0.041 (1)	0.0111 (7)	0.0122 (7)	0.0174 (8)
O5	0.064 (1)	0.0381 (9)	0.042 (1)	0.0119 (8)	0.0185 (9)	0.0155 (8)
O6	0.054 (1)	0.059 (1)	0.053 (1)	0.030 (1)	0.0071 (9)	0.015 (1)
N1	0.038 (1)	0.035 (1)	0.039 (1)	0.0112 (8)	0.0108 (8)	0.0186 (9)
N2	0.040 (1)	0.037 (1)	0.039 (1)	0.0135 (9)	0.0114 (9)	0.0191 (9)
C1	0.050 (2)	0.067 (2)	0.070 (2)	0.029 (2)	0.017 (2)	0.034 (2)
C2	0.042 (1)	0.037 (1)	0.051 (2)	0.010 (1)	0.015 (1)	0.023 (1)
C3	0.040 (1)	0.037 (1)	0.034 (1)	0.010 (1)	0.012 (1)	0.014 (1)
C4	0.042 (1)	0.035 (1)	0.037 (1)	0.009 (1)	0.005 (1)	0.019 (1)
C5	0.064 (2)	0.048 (2)	0.052 (2)	0.015 (1)	0.026 (1)	0.032 (1)
C6	0.069 (2)	0.054 (2)	0.055 (2)	0.026 (1)	0.035 (1)	0.032 (1)
C7	0.058 (2)	0.041 (1)	0.046 (2)	0.020 (1)	0.021 (1)	0.021 (1)
C8	0.074 (2)	0.044 (2)	0.060 (2)	0.010 (1)	0.021 (2)	0.027 (1)
C9	0.036 (1)	0.039 (1)	0.043 (1)	0.010 (1)	0.009 (1)	0.020 (1)
C10	0.037 (1)	0.042 (1)	0.036 (1)	0.009 (1)	0.009 (1)	0.016 (1)
C11	0.043 (1)	0.048 (1)	0.037 (1)	0.016 (1)	0.012 (1)	0.021 (1)
C12	0.037 (1)	0.060 (2)	0.044 (2)	0.011 (1)	0.006 (1)	0.027 (1)
C13	0.042 (1)	0.047 (1)	0.042 (1)	0.004 (1)	0.001 (1)	0.016 (1)
C14	0.047 (1)	0.037 (1)	0.042 (1)	0.007 (1)	0.006 (1)	0.015 (1)

Geometric parameters (Å, º)

Cu1—O1	1.979 (2)	C1—C2	1.506 (4)
Cu1—N1^i	1.997 (2)	C1—H1A	0.9600
Cu1—O2^i	2.586 (2)	C1—H1B	0.9600
Cu2—O4	1.975 (2)	C1—H1C	0.9600
Cu2—O5	2.614 (2)	C3—C4	1.389 (3)
Cu2—N2	2.014 (2)	C3—H3	0.9300
O1—C2	1.272 (3)	C4—C5	1.376 (4)
O2—C2	1.249 (3)	C5—C6	1.387 (4)
O4—C9	1.275 (3)	C5—H5	0.9300
O5—C9	1.244 (3)	C6—C7	1.381 (4)
Cu1—O1^i	1.979 (2)	C6—H6	0.9300
Cu1—N1	1.997 (2)	C7—H7	0.9300
Cu1—O2	2.586 (2)	C8—C9	1.509 (4)
Cu2—O4^ii	1.975 (2)	C8—H8A	0.9600
Cu2—O5^ii	2.614 (2)	C8—H8B	0.9600
Cu2—N2^ii	2.014 (2)	C8—H8C	0.9600
O3—C4	1.351 (3)	C10—C11	1.388 (3)
O3—H15	0.85 (3)	C10—H10	0.9300
O6—C11	1.354 (3)	C11—C12	1.377 (4)
O6—H16	0.85 (1)	C12—C13	1.378 (4)
N1—C3	1.337 (3)	C12—H12	0.9300
N1—C7	1.337 (3)	C13—C14	1.380 (4)
N2—C14	1.338 (3)	C13—H13	0.9300
N2—C10	1.339 (3)	C14—H14	0.9300
O1—Cu1—O2	55.76 (7)	N2—C10—H10	118.9
O1—Cu1—N1	89.89 (8)	N2—C14—C13	121.2 (2)
O2—Cu1—N1	93.72 (8)	N2—C14—H14	119.4
O4—Cu2—O5	55.23 (7)	N2—Cu2—N2^ii	180.0
O4—Cu2—N2	90.02 (8)	C2—O1—Cu1	105.2 (2)
N2—Cu2—O5	89.87 (8)	C4—O3—H15	110 (2)
N1—Cu1—N1^i	180.0 (3)	C2—O2—Cu1	77.5 (2)
N2—Cu2—N2^ii	180.0 (3)	C9—O5—Cu2	77.0 (2)
O1—Cu1—O1^i	180.00 (9)	C9—O4—Cu2	106.0 (2)
O1^i—Cu1—N1^i	89.89 (8)	C11—O6—H16	112 (3)
O1—Cu1—O2^i	124.3 (3)	C3—N1—C7	119.1 (2)
O4—Cu2—O5^ii	124.8 (3)	C3—N1—Cu1	119.9 (2)
O4^ii—Cu2—N2	89.98 (8)	C7—N1—Cu1	121.0 (2)
O1^i—Cu1—N1	90.11 (8)	C14—N2—C10	119.2 (2)
O1—Cu1—N1^i	90.11 (8)	C14—N2—Cu2	121.3 (2)
O1^i—Cu1—O2	124.3 (3)	C10—N2—Cu2	119.5 (2)
O1^i—Cu1—O2^i	55.76 (7)	C2—C1—H1A	109.5
O1—C2—C1	117.9 (3)	C2—C1—H1B	109.5
O2—Cu1—O2^i	180.0 (3)	C2—C1—H1C	109.5
O2—C2—O1	121.6 (2)	C4—C3—H3	118.8
O2—C2—C1	120.5 (3)	C4—C5—C6	119.2 (2)
O3—C4—C5	119.3 (2)	C4—C5—H5	120.4
O3—C4—C3	122.4 (2)	C5—C4—C3	118.3 (2)
O4—Cu2—O4^ii	180.0	C5—C6—H6	120.4
O4^ii—Cu2—O5^ii	55.23 (7)	C6—C5—H5	120.4
O4^ii—Cu2—O5	124.8 (3)	C6—C7—H7	119.2
O4—Cu2—N2^ii	89.98 (8)	C7—C6—C5	119.2 (3)
O4^ii—Cu2—N2^ii	90.02 (8)	C7—C6—H6	120.4
O4—C9—C8	117.4 (2)	C9—C8—H8A	109.5
O5—Cu2—O5^ii	180.0 (3)	C9—C8—H8B	109.5
O5—C9—O4	121.8 (2)	C9—C8—H8C	109.5
O5—C9—C8	120.8 (3)	C11—C10—H10	118.9
O6—C11—C12	119.7 (2)	C11—C12—C13	118.9 (2)
O6—C11—C10	121.7 (2)	C11—C12—H12	120.6
N1—Cu1—O2^i	86.3 (2)	C12—C11—C10	118.6 (2)
N1^i—Cu1—O2	86.3 (2)	C12—C13—C14	119.9 (2)
N1^i—Cu1—O2^i	93.72 (8)	C12—C13—H13	120.0
N1^i—Cu1—N1	180.0 (1)	C13—C12—H12	120.6
N1—C3—C4	122.5 (2)	C13—C14—H14	119.4
N1—C3—H3	118.8	C14—C13—H13	120.0
N1—C7—C6	121.6 (2)	H1A—C1—H1B	109.5
N1—C7—H7	119.2	H1A—C1—H1C	109.5
N2—Cu2—O5^ii	90.1 (2)	H1B—C1—H1C	109.5
N2^ii—Cu2—O5^ii	89.87 (8)	H8A—C8—H8B	109.5
N2^ii—Cu2—O5	90.1 (2)	H8A—C8—H8C	109.5
N2—C10—C11	122.2 (2)	H8B—C8—H8C	109.5
Cu1—O1—C2—O2	−1.7 (3)	N1^i—Cu1—O1—C2	−84.6 (2)
Cu1—O1—C2—C1	177.4 (2)	N1—Cu1—O1—C2	95.4 (2)
Cu1—N1—C3—C4	179.2 (2)	N1—C3—C4—O3	−178.2 (2)
Cu1—N1—C7—C6	−179.7 (2)	N1—C3—C4—C5	0.8 (4)
Cu2—O4—C9—O5	−0.4 (3)	N2—Cu2—O4—C9	90.0 (2)
Cu2—O4—C9—C8	−179.6 (2)	N2^ii—Cu2—O4—C9	−90.0 (2)
Cu2—N2—C10—C11	−179.2 (2)	N2—C10—C11—O6	179.3 (2)
Cu2—N2—C14—C13	179.3 (2)	N2—C10—C11—C12	−0.5 (4)
O1—Cu1—N1—C3	−139.2 (2)	C3—N1—C7—C6	0.5 (4)
O1^i—Cu1—N1—C3	40.8 (2)	C3—C4—C5—C6	−0.2 (4)
O1—Cu1—N1—C7	40.9 (2)	C4—C5—C6—C7	−0.3 (5)
O1^i—Cu1—N1—C7	−139.1 (2)	C5—C6—C7—N1	0.2 (4)
O3—C4—C5—C6	178.9 (3)	C7—N1—C3—C4	−1.0 (4)
O4—Cu2—N2—C14	36.2 (2)	C10—N2—C14—C13	−0.2 (4)
O4^ii—Cu2—N2—C14	−143.8 (2)	C10—C11—C12—C13	0.4 (4)
O4—Cu2—N2—C10	−144.4 (2)	C11—C12—C13—C14	−0.3 (4)
O4^ii—Cu2—N2—C10	35.6 (2)	C12—C13—C14—N2	0.2 (4)
O6—C11—C12—C13	−179.3 (3)	C14—N2—C10—C11	0.3 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H15···O5	0.85 (3)	1.78 (3)	2.632 (3)	175 (4)
O6—H16···O2	0.85 (3)	1.78 (1)	2.618 (3)	171 (4)