Bis[2-(2-hy-droxy-meth-yl)pyridine-κ(2)N,O](pivalato-κO)copper(II).

The structure of the centrosymmetric title complex, [Cu(C(5)H(9)O(2))(2)(C(6)H(7)NO)(2)], has the Cu(II) atom on a centre of inversion. The Cu(II) atom is six-coordinate with a distorted octa-hedral geometry, defined by the N and O atoms of the chelating 2-(2-hydroxymethyl)pyridine ligands and two carboxyl-ate O atoms from two monodentate pivalate ions. The crystal packing is stabilized by inter-molecular C-H⋯O and intra-molecular O-H⋯O hydrogen-bond inter-actions.

Related literature

For pyridine alcohol-based biomimetic sensors, see: Shaikh et al. (2010 ▶). For solid-state transformations, see: Shaikh et al. (2009 ▶, 2010 ▶). For structures with pyridine alcohols, see: Hamamci et al. (2004 ▶); Lah et al. (2006 ▶).

Experimental

Crystal data

[Cu(C5H9O2)2(C6H7NO)2]

M = 484.04

Monoclinic,

a = 9.797 (5) Å

b = 8.829 (5) Å

c = 13.674 (5) Å

β = 91.907 (5)°

V = 1182.1 (10) Å3

Z = 2

Cu Kα radiation

μ = 1.63 mm−1

T = 150 K

0.33 × 0.28 × 0.23 mm

Data collection

Oxford Super Nova diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.615, T max = 0.706

6929 measured reflections

2282 independent reflections

2052 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.119

S = 1.06

2282 reflections

146 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030917/bt5967sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030917/bt5967Isup2.hkl

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

[Cu(C5H9O2)2(C6H7NO)2]	F(000) = 510
Mr = 484.04	Dx = 1.360 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 3855 reflections
a = 9.797 (5) Å	θ = 3.2–71.6°
b = 8.829 (5) Å	µ = 1.63 mm−1
c = 13.674 (5) Å	T = 150 K
β = 91.907 (5)°	Block, blue
V = 1182.1 (10) Å3	0.33 × 0.28 × 0.23 mm
Z = 2

Oxford Super Nova diffractometer	2282 independent reflections
Radiation source: Micro-Focus (Cu) X-ray Source	2052 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 15.9948 pixels mm-1	θmax = 71.8°, θmin = 5.5°
ω/θ scans	h = −12→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −7→10
Tmin = 0.615, Tmax = 0.706	l = −16→16
6929 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.5457P] where P = (Fo2 + 2Fc2)/3
2282 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.54 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	0.5000	0.0000	0.5000	0.02121 (17)
O1	0.52417 (16)	−0.22601 (17)	0.40801 (10)	0.0281 (3)
O2	0.31138 (15)	−0.04928 (18)	0.54027 (11)	0.0284 (3)
O3	0.28735 (16)	−0.28213 (18)	0.47823 (11)	0.0323 (4)
N1	0.57203 (17)	−0.14564 (18)	0.59959 (12)	0.0231 (4)
C1	0.5683 (2)	−0.1127 (2)	0.69555 (15)	0.0266 (4)
H1	0.5305	−0.0185	0.7147	0.032*
C2	0.6170 (2)	−0.2102 (3)	0.76689 (16)	0.0315 (5)
H2	0.6142	−0.1836	0.8341	0.038*
C3	0.6701 (2)	−0.3477 (3)	0.73850 (18)	0.0347 (5)
H3	0.7055	−0.4168	0.7861	0.042*
C4	0.6712 (2)	−0.3839 (3)	0.63980 (18)	0.0325 (5)
H4	0.7049	−0.4792	0.6192	0.039*
C5	0.6222 (2)	−0.2788 (2)	0.57143 (15)	0.0251 (4)
C6	0.6241 (2)	−0.3092 (3)	0.46280 (17)	0.0323 (5)
H6A	0.7156	−0.2834	0.4390	0.039*
H6B	0.6090	−0.4186	0.4512	0.039*
C7	0.2550 (2)	−0.1780 (2)	0.53540 (13)	0.0227 (4)
C8	0.1446 (2)	−0.2117 (3)	0.60946 (15)	0.0280 (5)
C9	0.2209 (3)	−0.2819 (4)	0.6974 (2)	0.0605 (9)
H9A	0.2864	−0.2085	0.7251	0.091*
H9B	0.2696	−0.3726	0.6765	0.091*
H9C	0.1555	−0.3097	0.7470	0.091*
C10	0.0713 (3)	−0.0693 (4)	0.6412 (2)	0.0593 (8)
H10A	0.1382	0.0035	0.6680	0.089*
H10B	0.0061	−0.0950	0.6914	0.089*
H10C	0.0223	−0.0244	0.5847	0.089*
C11	0.0425 (3)	−0.3258 (4)	0.5677 (2)	0.0659 (10)
H11A	0.0909	−0.4175	0.5480	0.099*
H11B	−0.0059	−0.2819	0.5105	0.099*
H11C	−0.0233	−0.3516	0.6174	0.099*
H101	0.434 (4)	−0.251 (4)	0.428 (2)	0.053 (9)*

	U11	U22	U33	U12	U13	U23
Cu1	0.0266 (3)	0.0185 (3)	0.0187 (3)	−0.00076 (14)	0.00306 (17)	0.00341 (14)
O1	0.0340 (8)	0.0301 (8)	0.0206 (7)	0.0000 (6)	0.0055 (6)	−0.0007 (6)
O2	0.0301 (8)	0.0233 (8)	0.0323 (8)	−0.0012 (6)	0.0069 (6)	0.0034 (6)
O3	0.0342 (8)	0.0389 (9)	0.0242 (7)	−0.0084 (6)	0.0074 (6)	−0.0125 (6)
N1	0.0272 (8)	0.0205 (8)	0.0219 (8)	−0.0017 (6)	0.0033 (6)	0.0019 (6)
C1	0.0305 (10)	0.0265 (10)	0.0229 (10)	−0.0038 (8)	0.0003 (8)	−0.0007 (8)
C2	0.0338 (11)	0.0375 (12)	0.0229 (10)	−0.0062 (9)	−0.0033 (8)	0.0053 (9)
C3	0.0305 (11)	0.0359 (12)	0.0371 (12)	−0.0027 (9)	−0.0050 (9)	0.0155 (10)
C4	0.0310 (11)	0.0247 (11)	0.0419 (13)	0.0032 (8)	0.0010 (9)	0.0074 (9)
C5	0.0255 (10)	0.0219 (10)	0.0282 (11)	−0.0009 (8)	0.0032 (8)	0.0024 (8)
C6	0.0370 (12)	0.0304 (11)	0.0298 (11)	0.0056 (9)	0.0068 (9)	−0.0018 (9)
C7	0.0260 (10)	0.0271 (10)	0.0148 (9)	−0.0013 (8)	−0.0011 (7)	0.0008 (7)
C8	0.0300 (11)	0.0317 (11)	0.0228 (10)	−0.0058 (8)	0.0069 (8)	−0.0031 (8)
C9	0.0534 (18)	0.096 (2)	0.0332 (14)	0.0017 (16)	0.0136 (12)	0.0251 (15)
C10	0.0640 (19)	0.0502 (18)	0.066 (2)	0.0039 (14)	0.0370 (16)	−0.0086 (15)
C11	0.0546 (18)	0.088 (2)	0.0568 (18)	−0.0427 (17)	0.0249 (15)	−0.0278 (17)

Cu1—N1	1.9855 (17)	C4—H4	0.9500
Cu1—N1i	1.9855 (17)	C5—C6	1.510 (3)
Cu1—O2	1.9937 (17)	C6—H6A	0.9900
Cu1—O2i	1.9937 (17)	C6—H6B	0.9900
Cu1—O1i	2.3748 (18)	C7—O3	1.254 (3)
Cu1—O1	2.3748 (18)	C7—C8	1.535 (3)
O1—C6	1.418 (3)	C8—C11	1.518 (3)
O1—H101	0.95 (4)	C8—C10	1.518 (4)
O2—C7	1.265 (3)	C8—C9	1.526 (4)
O3—C7	1.254 (3)	C9—H9A	0.9800
N1—C5	1.336 (3)	C9—H9B	0.9800
N1—C1	1.346 (3)	C9—H9C	0.9800
C1—C2	1.375 (3)	C10—H10A	0.9800
C1—H1	0.9500	C10—H10B	0.9800
C2—C3	1.382 (4)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.387 (4)	C11—H11B	0.9800
C3—H3	0.9500	C11—H11C	0.9800
C4—C5	1.391 (3)
N1—Cu1—N1i	180.00 (7)	C4—C5—C6	121.8 (2)
N1—Cu1—O2	88.90 (7)	O1—C6—C5	113.40 (18)
N1i—Cu1—O2	91.10 (7)	O1—C6—H6A	108.9
N1—Cu1—O2i	91.10 (7)	C5—C6—H6A	108.9
N1i—Cu1—O2i	88.90 (7)	O1—C6—H6B	108.9
O2—Cu1—O2i	180.0	C5—C6—H6B	108.9
N1—Cu1—O1i	102.73 (7)	H6A—C6—H6B	107.7
N1i—Cu1—O1i	77.27 (7)	O3—C7—O2	124.95 (19)
O2—Cu1—O1i	85.84 (6)	O3—C7—O2	124.95 (19)
O2i—Cu1—O1i	94.16 (6)	O3—C7—C8	117.88 (18)
N1—Cu1—O1	77.27 (7)	O3—C7—C8	117.88 (18)
N1i—Cu1—O1	102.73 (7)	O2—C7—C8	117.07 (17)
O2—Cu1—O1	94.16 (6)	C11—C8—C10	110.2 (2)
O2i—Cu1—O1	85.84 (6)	C11—C8—C9	109.0 (3)
O1i—Cu1—O1	180.0	C10—C8—C9	109.6 (2)
C6—O1—Cu1	103.56 (12)	C11—C8—C7	110.48 (18)
C6—O1—H101	111 (2)	C10—C8—C7	112.25 (19)
Cu1—O1—H101	86.1 (19)	C9—C8—C7	105.14 (19)
C7—O2—Cu1	126.06 (13)	C8—C9—H9A	109.5
C5—N1—C1	119.59 (18)	C8—C9—H9B	109.5
C5—N1—Cu1	119.87 (14)	H9A—C9—H9B	109.5
C1—N1—Cu1	120.52 (14)	C8—C9—H9C	109.5
N1—C1—C2	122.4 (2)	H9A—C9—H9C	109.5
N1—C1—H1	118.8	H9B—C9—H9C	109.5
C2—C1—H1	118.8	C8—C10—H10A	109.5
C1—C2—C3	118.4 (2)	C8—C10—H10B	109.5
C1—C2—H2	120.8	H10A—C10—H10B	109.5
C3—C2—H2	120.8	C8—C10—H10C	109.5
C2—C3—C4	119.4 (2)	H10A—C10—H10C	109.5
C2—C3—H3	120.3	H10B—C10—H10C	109.5
C4—C3—H3	120.3	C8—C11—H11A	109.5
C3—C4—C5	119.1 (2)	C8—C11—H11B	109.5
C3—C4—H4	120.4	H11A—C11—H11B	109.5
C5—C4—H4	120.4	C8—C11—H11C	109.5
N1—C5—C4	121.0 (2)	H11A—C11—H11C	109.5
N1—C5—C6	117.14 (18)	H11B—C11—H11C	109.5
N1—Cu1—O1—C6	−23.50 (13)	Cu1—N1—C5—C4	−178.92 (16)
N1i—Cu1—O1—C6	156.50 (13)	C1—N1—C5—C6	−179.83 (19)
O2—Cu1—O1—C6	−111.43 (13)	Cu1—N1—C5—C6	1.5 (2)
O2i—Cu1—O1—C6	68.57 (13)	C3—C4—C5—N1	−1.3 (3)
N1—Cu1—O2—C7	−61.13 (16)	C3—C4—C5—C6	178.2 (2)
N1i—Cu1—O2—C7	118.87 (16)	Cu1—O1—C6—C5	30.6 (2)
O1i—Cu1—O2—C7	−163.98 (16)	N1—C5—C6—O1	−25.3 (3)
O1—Cu1—O2—C7	16.02 (16)	C4—C5—C6—O1	155.2 (2)
O2—Cu1—N1—C5	106.78 (16)	O3—O3—C7—O2	0.00 (19)
O2i—Cu1—N1—C5	−73.22 (16)	O3—O3—C7—C8	0.00 (10)
O1i—Cu1—N1—C5	−167.74 (15)	Cu1—O2—C7—O3	−24.1 (3)
O1—Cu1—N1—C5	12.26 (15)	Cu1—O2—C7—O3	−24.1 (3)
O2—Cu1—N1—C1	−71.87 (16)	Cu1—O2—C7—C8	152.14 (14)
O2i—Cu1—N1—C1	108.13 (16)	O3—C7—C8—C11	−31.3 (3)
O1i—Cu1—N1—C1	13.62 (16)	O3—C7—C8—C11	−31.3 (3)
O1—Cu1—N1—C1	−166.38 (16)	O2—C7—C8—C11	152.3 (2)
C5—N1—C1—C2	1.4 (3)	O3—C7—C8—C10	−154.7 (2)
Cu1—N1—C1—C2	−179.99 (16)	O3—C7—C8—C10	−154.7 (2)
N1—C1—C2—C3	−0.8 (3)	O2—C7—C8—C10	28.8 (3)
C1—C2—C3—C4	−0.8 (3)	O3—C7—C8—C9	86.3 (2)
C2—C3—C4—C5	1.8 (3)	O3—C7—C8—C9	86.3 (2)
C1—N1—C5—C4	−0.3 (3)	O2—C7—C8—C9	−90.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O3	0.95 (4)	1.64 (4)	2.588 (2)	171 (3)
C2—H2···O3ii	0.95	2.57	3.289 (3)	132
C4—H4···O3iii	0.95	2.50	3.392 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O3	0.95 (4)	1.64 (4)	2.588 (2)	171 (3)
C2—H2⋯O3i	0.95	2.57	3.289 (3)	132
C4—H4⋯O3ii	0.95	2.50	3.392 (3)	157

Symmetry codes: (i) ; (ii) .