Diaqua­sodium(I) perchlorate bis­[μ-2-(carboxyl­atomethyl­imino­meth­yl)phenolato]bis­[(3-methyl­pyridine)copper(II)]

Wen, X.; Liu, Y.; Li, Z.

doi:10.1107/S1600536808039561

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page m1634

doi:10.1107/S1600536808039561

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Diaquasodium(I) perchlorate bis[μ-2-(carboxylatomethyliminomethyl)phenolato]bis[(3-methylpyridine)copper(II)]

Xiangru Wen,^a Yongmin Liu ^a and Zhengyi Li ^a ^*

^aXuzhou Medical College, Xuzhou 221004, People's Republic of China
^*Correspondence e-mail: chemlzy@yahoo.com.cn

(Received 31 October 2008; accepted 24 November 2008; online 29 November 2008)

In the title compound, [Na(H₂O)₂]ClO₄·[Cu₂(C₉H₇NO₃)₂(C₆H₇N)₂], the Cu^II atom is coordinated by one N atom and two O atoms from a tridentate N-salicylideneglycinate Schiff base dianion and one N atom from a 3-methylpyridine ligand. Longer Cu⋯O contacts [2.680 (2) Å] complete an approximate square-based pyramidal coordination geometry around Cu^II, forming a dimeric complex across a centre of inversion. The dimeric complexes form stacks along the a axis, with Cu⋯O contacts of 3.332 (2) Å between them. The Na⁺ cations and perchlorate anions lie on twofold rotation axes between the stacks. The former are coordinated by two disordered water molecules (each with half-occupancy), and form Na⋯O contacts of 3.698 (3) Å to the perchlorate anions and Na⋯π contacts to neighbouring salicylideneglycinate ligands [shortest Na⋯C = 3.516 (3) Å].

Related literature

For related structures, see: Warda (1998a ,b ,c ,d ). For synthesis details, see: Ueki et al. (1967 ); Warda (1994 ).

Experimental

Crystal data

[Na(H₂O)₂]ClO₄·[Cu₂(C₉H₇NO₃)₂(C₆H₇N)₂]
M_r = 826.12
Monoclinic, P 2/c
a = 7.4677 (5) Å
b = 13.2402 (9) Å
c = 19.3937 (12) Å
β = 109.165 (2)°
V = 1811.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 292 (2) K
0.30 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.68, T_max = 0.73
18486 measured reflections
3558 independent reflections
2926 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.100
S = 1.13
3558 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039561/bi2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039561/bi2318Isup2.hkl

checkCIF report

Comment top

Copper(II) complexes with tridentate Schiff-base dianions of the N-salicylideneaminoacidato type (TSB^2-) have been reported recently (1998a–d). These complexes are pyridine adducts. In this paper, we present the structure of the related title compound.

The Cu^II atom is coordinated by the tridentate N-salicylideneglycinato dianion and the 2-methylpyridine ligand in an approximately square-planar geometry. The pyridine ring is inclined with respect to the mean plane (through O1, O2, N1 and N2) at an angle of 11.5 (2) ° and the Cu^II atom lies 0.042 (1) Å out of this plane. The Cu—N and Cu—O bond distances [Cu—N 1.919 (2) and 2.018 (2) Å; Cu—O 1.922 (2) and 1.966 (2) Å] do not differ significantly when compared to the 2-ethylpyridine compound (Warda, 1998c). These units are associated into dimers through Cu···O interactions (2.680 (2) Å), and these dimers are associated into stacks along the a axis of the monoclinic unit cell by longer Cu···O contacts (3.332 (2) Å) (Fig. 2). The Na⁺ cations and perchlorate anions lie between stacks, both on 2-fold axes, forming Na···O contacts of 3.698 (2) Å. The Na⁺ cation is also coordinated by two water molecules in a bent geometry.

Related literature top

For related structures, see: Warda (1998a,b,c,d). For synthesis details, see: Ueki et al. (1967); Warda (1994).

Experimental top

The title compound was synthesized from aqua(N-salicylideneglycinato)copper(II) hemihydrate according to the methods of Ueki et al. (1967) and Warda (1994), with 3-methylpyridine and sodium perchlorate in a 4:3 ethanol-water mixture at room temperature. Dark-green prismatic crystals grew within a few days.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms [symmetry codes: (A) 1 - x, 2 - y, 1 - z; (B) -x, y, -z + 1/2]. H atoms of the water molecules are omitted.
	Fig. 2. One-dimensional stack running along the a axis.

Diaquasodium(I) perchlorate bis[µ-2-(carboxylatomethyliminomethyl)phenolato]bis[(3- methylpyridine)copper(II)] top

Crystal data top

[Na(H₂O)₂]ClO₄·[Cu₂(C₉H₇NO₃)₂(C₆H₇N)₂]	F(000) = 844
M_r = 826.12	D_x = 1.515 Mg m⁻³
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 7803 reflections
a = 7.4677 (5) Å	θ = 2.2–26.9°
b = 13.2402 (9) Å	µ = 1.32 mm⁻¹
c = 19.3937 (12) Å	T = 292 K
β = 109.165 (2)°	Block, dark-green
V = 1811.3 (2) Å³	0.30 × 0.26 × 0.24 mm
Z = 2

Data collection top

Bruker SMART APEX CCD diffractometer	3558 independent reflections
Radiation source: sealed tube	2926 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.68, T_max = 0.73	k = −16→16
18486 measured reflections	l = −23→23

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0394P)² + 1.073P] where P = (F_o² + 2F_c²)/3
3558 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Na(H₂O)₂]ClO₄·[Cu₂(C₉H₇NO₃)₂(C₆H₇N)₂]	V = 1811.3 (2) Å³
M_r = 826.12	Z = 2
Monoclinic, P2/c	Mo Kα radiation
a = 7.4677 (5) Å	µ = 1.32 mm⁻¹
b = 13.2402 (9) Å	T = 292 K
c = 19.3937 (12) Å	0.30 × 0.26 × 0.24 mm
β = 109.165 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	3558 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2926 reflections with I > 2σ(I)
T_min = 0.68, T_max = 0.73	R_int = 0.047
18486 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.13	Δρ_max = 0.29 e Å⁻³
3558 reflections	Δρ_min = −0.59 e Å⁻³
237 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.1080 (4)	0.8274 (2)	0.06545 (17)	0.0359 (6)
C2	0.0762 (5)	0.7877 (3)	0.1253 (2)	0.0514 (9)
H2	0.0667	0.8309	0.1618	0.062*
C3	0.0578 (5)	0.6847 (3)	0.1330 (2)	0.0555 (9)
H3	0.0363	0.6610	0.1748	0.067*
C4	0.0695 (5)	0.6178 (3)	0.0832 (2)	0.0566 (10)
H4	0.0577	0.5489	0.0901	0.068*
C5	0.1000 (5)	0.6543 (2)	0.0206 (2)	0.0526 (9)
H5	0.1067	0.6090	−0.0151	0.063*
C6	0.1203 (4)	0.7558 (2)	0.01060 (18)	0.0411 (7)
C7	0.1447 (4)	0.7882 (2)	−0.05710 (19)	0.0412 (7)
H7	0.1370	0.7392	−0.0923	0.049*
C8	0.1947 (5)	0.8996 (3)	−0.14394 (17)	0.0499 (9)
H8A	0.0710	0.8977	−0.1814	0.060*
H8B	0.2744	0.8488	−0.1553	0.060*
C9	0.2828 (5)	1.0035 (2)	−0.1416 (2)	0.0478 (8)
C10	0.2917 (4)	1.1111 (3)	0.12608 (17)	0.0427 (7)
H10	0.2641	1.0502	0.1443	0.051*
C11	0.3191 (6)	1.1968 (3)	0.1690 (2)	0.0567 (10)
H11	0.3069	1.1936	0.2152	0.068*
C12	0.3636 (6)	1.2851 (3)	0.1439 (2)	0.0610 (10)
H12	0.3780	1.3432	0.1721	0.073*
C13	0.3882 (5)	1.2894 (3)	0.0754 (2)	0.0547 (9)
C14	0.3530 (4)	1.1998 (2)	0.03434 (18)	0.0421 (7)
H14	0.3645	1.2004	−0.0120	0.050*
C15	0.4383 (6)	1.3829 (3)	0.0458 (2)	0.0591 (10)
H15A	0.4325	1.4385	0.0768	0.089*
H15B	0.3508	1.3942	−0.0024	0.089*
H15C	0.5645	1.3773	0.0436	0.089*
Cl1	0.0000	0.39685 (9)	0.2500	0.0541 (3)
Cu1	0.22475 (5)	0.99364 (3)	−0.007850 (19)	0.03341 (12)
N1	0.1759 (4)	0.87901 (19)	−0.07187 (12)	0.0360 (6)
N2	0.3039 (3)	1.11394 (19)	0.05920 (13)	0.0351 (5)
Na1	0.5000	0.60089 (17)	0.2500	0.0603 (5)
O1	0.1223 (3)	0.92455 (16)	0.05801 (12)	0.0424 (5)
O2	0.3196 (4)	1.05246 (17)	−0.08228 (13)	0.0500 (6)
O3	0.3162 (4)	1.0293 (2)	−0.19675 (15)	0.0616 (7)
O4	0.0491 (4)	0.45860 (19)	0.19803 (14)	0.0574 (7)
O5	0.1612 (3)	0.33292 (18)	0.28823 (14)	0.0514 (6)
O6	0.6028 (7)	0.6382 (4)	0.1670 (3)	0.0507 (13)	0.50
H6B	0.5176	0.6692	0.1335	0.061*	0.50
H6C	0.6993	0.6761	0.1836	0.061*	0.50
O7	0.3968 (8)	0.6975 (5)	0.3137 (3)	0.0594 (15)	0.50
H7A	0.3624	0.6626	0.3439	0.071*	0.50
H7B	0.4843	0.7379	0.3367	0.071*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0305 (15)	0.0368 (16)	0.0413 (16)	−0.0021 (12)	0.0130 (13)	0.0045 (13)
C2	0.0444 (19)	0.058 (2)	0.048 (2)	−0.0021 (16)	0.0099 (16)	0.0147 (17)
C3	0.052 (2)	0.051 (2)	0.061 (2)	0.0009 (17)	0.0157 (18)	0.0150 (19)
C4	0.055 (2)	0.045 (2)	0.065 (2)	−0.0103 (17)	0.0127 (18)	0.0103 (18)
C5	0.056 (2)	0.0319 (17)	0.066 (2)	−0.0034 (15)	0.0139 (18)	0.0067 (16)
C6	0.0376 (16)	0.0337 (15)	0.0485 (18)	0.0022 (13)	0.0095 (14)	0.0042 (14)
C7	0.0358 (16)	0.0351 (16)	0.0522 (19)	−0.0062 (13)	0.0136 (14)	−0.0014 (14)
C8	0.055 (2)	0.067 (2)	0.0334 (16)	−0.0200 (17)	0.0218 (15)	−0.0045 (16)
C9	0.065 (2)	0.0381 (17)	0.052 (2)	0.0002 (16)	0.0349 (17)	0.0000 (16)
C10	0.0340 (16)	0.053 (2)	0.0415 (17)	−0.0102 (14)	0.0130 (13)	−0.0108 (15)
C11	0.077 (3)	0.056 (2)	0.0450 (19)	−0.0183 (19)	0.0306 (19)	−0.0130 (17)
C12	0.061 (2)	0.058 (2)	0.064 (2)	−0.0098 (19)	0.020 (2)	−0.0130 (19)
C13	0.0367 (18)	0.051 (2)	0.070 (2)	−0.0031 (15)	0.0088 (17)	−0.0139 (18)
C14	0.0388 (17)	0.0453 (18)	0.0434 (18)	−0.0032 (14)	0.0153 (14)	−0.0029 (14)
C15	0.062 (2)	0.048 (2)	0.063 (2)	−0.0155 (18)	0.0148 (19)	−0.0123 (18)
Cl1	0.0648 (8)	0.0430 (6)	0.0597 (7)	0.000	0.0273 (6)	0.000
Cu1	0.0428 (2)	0.02850 (19)	0.0342 (2)	−0.00470 (15)	0.01980 (15)	−0.00310 (14)
N1	0.0465 (15)	0.0336 (13)	0.0289 (12)	−0.0045 (11)	0.0139 (11)	−0.0045 (10)
N2	0.0326 (13)	0.0361 (13)	0.0334 (12)	−0.0041 (10)	0.0066 (10)	−0.0057 (10)
Na1	0.0548 (12)	0.0636 (13)	0.0564 (12)	0.000	0.0101 (10)	0.000
O1	0.0638 (14)	0.0314 (11)	0.0413 (12)	−0.0030 (10)	0.0297 (11)	0.0032 (9)
O2	0.0768 (17)	0.0352 (12)	0.0503 (14)	−0.0093 (11)	0.0377 (13)	−0.0029 (11)
O3	0.0747 (18)	0.0602 (16)	0.0606 (16)	−0.0068 (13)	0.0369 (14)	0.0063 (13)
O4	0.0772 (18)	0.0495 (14)	0.0599 (15)	−0.0009 (13)	0.0419 (14)	−0.0033 (12)
O5	0.0493 (13)	0.0464 (14)	0.0601 (15)	0.0014 (11)	0.0202 (12)	0.0037 (11)
O6	0.036 (3)	0.060 (3)	0.047 (3)	−0.012 (3)	0.001 (2)	−0.012 (3)
O7	0.046 (3)	0.059 (4)	0.065 (4)	−0.009 (3)	0.007 (3)	−0.014 (3)

Geometric parameters (Å, º) top

C1—O1	1.303 (4)	C12—C13	1.401 (6)
C1—C2	1.364 (5)	C12—H12	0.930
C1—C6	1.450 (5)	C13—C14	1.405 (5)
C2—C3	1.384 (5)	C13—C15	1.464 (5)
C2—H2	0.930	C14—N2	1.333 (4)
C3—C4	1.334 (5)	C14—H14	0.930
C3—H3	0.930	C15—H15A	0.960
C4—C5	1.393 (5)	C15—H15B	0.960
C4—H4	0.930	C15—H15C	0.960
C5—C6	1.373 (5)	Cl1—O4	1.436 (3)
C5—H5	0.930	Cl1—O4ⁱ	1.436 (3)
C6—C7	1.448 (5)	Cl1—O5ⁱ	1.459 (2)
C7—N1	1.275 (4)	Cl1—O5	1.459 (2)
C7—H7	0.930	Cu1—N1	1.919 (2)
C8—N1	1.475 (4)	Cu1—O1	1.922 (2)
C8—C9	1.519 (5)	Cu1—O2	1.966 (2)
C8—H8A	0.970	Cu1—N2	2.018 (2)
C8—H8B	0.970	Na1—O6	2.058 (6)
C9—O3	1.224 (4)	Na1—O6ⁱⁱ	2.058 (6)
C9—O2	1.269 (4)	Na1—O7ⁱⁱ	2.093 (6)
C10—N2	1.330 (4)	Na1—O7	2.093 (6)
C10—C11	1.382 (5)	O6—H6B	0.850
C10—H10	0.930	O6—H6C	0.850
C11—C12	1.349 (5)	O7—H7A	0.850
C11—H11	0.930	O7—H7B	0.850

O1—C1—C2	121.2 (3)	C14—C13—C15	121.1 (4)
O1—C1—C6	122.5 (3)	N2—C14—C13	122.5 (3)
C2—C1—C6	116.3 (3)	N2—C14—H14	118.7
C1—C2—C3	121.5 (4)	C13—C14—H14	118.7
C1—C2—H2	119.2	C13—C15—H15A	109.5
C3—C2—H2	119.2	C13—C15—H15B	109.5
C4—C3—C2	122.9 (4)	H15A—C15—H15B	109.5
C4—C3—H3	118.5	C13—C15—H15C	109.5
C2—C3—H3	118.5	H15A—C15—H15C	109.5
C3—C4—C5	118.0 (3)	H15B—C15—H15C	109.5
C3—C4—H4	121.0	O4—Cl1—O4ⁱ	110.6 (2)
C5—C4—H4	121.0	O4—Cl1—O5ⁱ	109.39 (15)
C6—C5—C4	121.3 (4)	O4ⁱ—Cl1—O5ⁱ	109.18 (14)
C6—C5—H5	119.3	O4—Cl1—O5	109.18 (14)
C4—C5—H5	119.3	O4ⁱ—Cl1—O5	109.39 (15)
C5—C6—C7	118.1 (3)	O5ⁱ—Cl1—O5	109.1 (2)
C5—C6—C1	120.0 (3)	N1—Cu1—O1	91.20 (10)
C7—C6—C1	121.9 (3)	N1—Cu1—O2	82.87 (10)
N1—C7—C6	124.7 (3)	O1—Cu1—O2	174.01 (9)
N1—C7—H7	117.6	N1—Cu1—N2	174.05 (10)
C6—C7—H7	117.6	O1—Cu1—N2	92.51 (10)
N1—C8—C9	108.3 (3)	O2—Cu1—N2	93.47 (10)
N1—C8—H8A	110.0	C7—N1—C8	117.9 (3)
C9—C8—H8A	110.0	C7—N1—Cu1	127.6 (2)
N1—C8—H8B	110.0	C8—N1—Cu1	114.2 (2)
C9—C8—H8B	110.0	C10—N2—C14	119.5 (3)
H8A—C8—H8B	108.4	C10—N2—Cu1	120.4 (2)
O3—C9—O2	127.1 (3)	C14—N2—Cu1	119.8 (2)
O3—C9—C8	115.9 (3)	O6—Na1—O6ⁱⁱ	152.2 (3)
O2—C9—C8	116.9 (3)	O6ⁱⁱ—Na1—O7ⁱⁱ	128.2 (3)
N2—C10—C11	121.3 (3)	O6—Na1—O7	128.2 (3)
N2—C10—H10	119.3	O7ⁱⁱ—Na1—O7	104.7 (4)
C11—C10—H10	119.3	C1—O1—Cu1	127.5 (2)
C12—C11—C10	120.0 (3)	C9—O2—Cu1	116.1 (2)
C12—C11—H11	120.0	Na1—O6—H6B	109.6
C10—C11—H11	120.0	Na1—O6—H6C	109.5
C11—C12—C13	120.1 (4)	H6B—O6—H6C	109.4
C11—C12—H12	119.9	Na1—O7—H7A	109.1
C13—C12—H12	119.9	Na1—O7—H7B	109.0
C12—C13—C14	116.4 (4)	H7A—O7—H7B	109.6
C12—C13—C15	122.4 (3)

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

Experimental details

Crystal data
Chemical formula	[Na(H₂O)₂]ClO₄·[Cu₂(C₉H₇NO₃)₂(C₆H₇N)₂]
M_r	826.12
Crystal system, space group	Monoclinic, P2/c
Temperature (K)	292
a, b, c (Å)	7.4677 (5), 13.2402 (9), 19.3937 (12)
β (°)	109.165 (2)
V (Å³)	1811.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.68, 0.73
No. of measured, independent and observed [I > 2σ(I)] reflections	18486, 3558, 2926
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.100, 1.13
No. of reflections	3558
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.59

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

References

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