{μ-6,6'-Dimeth-oxy-2,2'-[1,2-phenyl-ene-bis(nitrilo-methyl-idyne)]diphenolato}methano-lcopper(II)sodium(I).

In the title complex, [NaCu(C(22)H(18)N(2)O(4))Cl(CH(3)OH)], the Cu atom lies nearly in the plane defined by the N(2)O(2) core of donor atoms, the out-of-plane distance being 0.001 (2) Å. The anion provides a planar cavity of four O atoms which accommodates a sodium cation. The coordination geometry around sodium is completed by the methanol O atom and a chloride ion. The four O atoms define a coordination plane containing the sodium cation [maximum displacement from the mean plane through the five atoms = 0.152 (3) Å for Na]. The crystal structure is stabilized by inter-molecular C-H⋯Cl and O-H⋯Cl hydrogen bonds, which link the mol-ecules into dimers. The crystal packing is further stabilized by weak π-π stacking inter-actions [centroid-centroid distances of 3.442 (4), 3.482 (3), 3.350 (2), 3.531 (4) 3.575 (2) and 3.604 (2) Å].

Related literature

For related literature, see: Molina et al. (1998 ▶); Lo et al. (2004 ▶, 2006 ▶).

Experimental

Crystal data

[NaCu(C22H18N2O4)Cl(CH4O)]

M = 528.41

Monoclinic,

a = 11.7986 (2) Å

b = 7.9657 (2) Å

c = 23.8291 (3) Å

β = 93.283 (2)°

V = 2235.88 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.16 mm−1

T = 295 (2) K

0.22 × 0.18 × 0.12 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.785, T max = 0.874

20679 measured reflections

4620 independent reflections

3958 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.083

S = 1.02

4620 reflections

302 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008453/hg2383sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008453/hg2383Isup2.hkl

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

[NaCu(C22H18N2O4)Cl(CH4O)]	F000 = 1084
Mr = 528.41	Dx = 1.570 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3689 reflections
a = 11.7986 (2) Å	θ = 2.2–26.6º
b = 7.9657 (2) Å	µ = 1.16 mm−1
c = 23.8291 (3) Å	T = 295 (2) K
β = 93.283 (2)º	Block, brown
V = 2235.88 (7) Å3	0.22 × 0.18 × 0.12 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	4620 independent reflections
Radiation source: fine-focus sealed tube	3958 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
Detector resolution: 0 pixels mm-1	θmax = 26.5º
T = 295(2) K	θmin = 1.7º
φ and ω scans	h = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	k = −10→10
Tmin = 0.785, Tmax = 0.874	l = −27→29
20679 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0451P)2 + 1.0557P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4620 reflections	Δρmax = 0.39 e Å−3
302 parameters	Δρmin = −0.24 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.245877 (17)	0.00018 (3)	0.488480 (9)	0.03216 (8)
Na1	0.28232 (7)	−0.09373 (11)	0.62911 (3)	0.0476 (2)
N1	0.32603 (13)	−0.03020 (18)	0.42070 (6)	0.0325 (3)
N2	0.14259 (12)	0.13666 (19)	0.44095 (6)	0.0343 (3)
O1	0.45834 (12)	−0.3066 (2)	0.61004 (6)	0.0500 (4)
O2	0.34391 (10)	−0.14186 (16)	0.53338 (5)	0.0364 (3)
O3	0.16904 (11)	0.04016 (17)	0.55486 (5)	0.0387 (3)
O4	0.10358 (13)	0.0706 (2)	0.65442 (6)	0.0577 (4)
O5	0.20263 (19)	−0.3239 (2)	0.67333 (9)	0.0760 (5)
Cl1	0.39839 (5)	0.09785 (10)	0.70798 (3)	0.0707 (2)
C1	0.5137 (2)	−0.4081 (4)	0.65277 (10)	0.0664 (7)
H1A	0.4732	−0.4008	0.6865	0.100*
H1B	0.5900	−0.3690	0.6602	0.100*
H1C	0.5150	−0.5227	0.6404	0.100*
C2	0.50487 (15)	−0.3024 (2)	0.55889 (8)	0.0358 (4)
C3	0.60488 (16)	−0.3766 (2)	0.54631 (9)	0.0410 (4)
H3	0.6460	−0.4385	0.5736	0.049*
C4	0.64579 (16)	−0.3597 (2)	0.49238 (9)	0.0427 (4)
H4	0.7142	−0.4096	0.4842	0.051*
C5	0.58578 (15)	−0.2708 (2)	0.45224 (9)	0.0382 (4)
H5	0.6142	−0.2593	0.4168	0.046*
C6	0.48040 (14)	−0.1950 (2)	0.46330 (8)	0.0324 (4)
C7	0.43811 (14)	−0.2087 (2)	0.51781 (7)	0.0308 (4)
C8	0.42240 (14)	−0.1073 (2)	0.41826 (7)	0.0334 (4)
H8	0.4566	−0.1051	0.3841	0.040*
C9	0.27193 (15)	0.0517 (2)	0.37354 (8)	0.0360 (4)
C10	0.30926 (19)	0.0474 (3)	0.31902 (9)	0.0488 (5)
H10	0.3754	−0.0099	0.3116	0.059*
C11	0.2474 (2)	0.1286 (3)	0.27618 (9)	0.0604 (6)
H11	0.2718	0.1248	0.2398	0.072*
C12	0.1496 (2)	0.2153 (3)	0.28688 (10)	0.0603 (6)
H12	0.1087	0.2693	0.2576	0.072*
C13	0.11237 (18)	0.2224 (3)	0.34051 (9)	0.0506 (5)
H13	0.0468	0.2818	0.3475	0.061*
C14	0.17298 (15)	0.1405 (2)	0.38442 (8)	0.0371 (4)
C15	0.05522 (15)	0.2153 (2)	0.45833 (8)	0.0395 (4)
H15	0.0102	0.2733	0.4315	0.047*
C16	0.02163 (15)	0.2213 (2)	0.51487 (9)	0.0391 (4)
C17	−0.07586 (17)	0.3182 (3)	0.52576 (11)	0.0521 (5)
H17	−0.1154	0.3727	0.4962	0.063*
C18	−0.11214 (19)	0.3325 (3)	0.57844 (11)	0.0603 (6)
H18	−0.1764	0.3958	0.5847	0.072*
C19	−0.05333 (18)	0.2524 (3)	0.62352 (10)	0.0545 (6)
H19	−0.0778	0.2646	0.6597	0.065*
C20	0.04028 (16)	0.1560 (3)	0.61461 (9)	0.0429 (4)
C21	0.08043 (14)	0.1367 (2)	0.55956 (8)	0.0356 (4)
C22	0.0796 (2)	0.0956 (4)	0.71220 (9)	0.0702 (7)
H22A	0.1302	0.0282	0.7358	0.105*
H22B	0.0026	0.0635	0.7177	0.105*
H22C	0.0899	0.2118	0.7218	0.105*
C23	0.2056 (3)	−0.4837 (4)	0.64857 (15)	0.0820 (9)
H23A	0.1700	−0.5636	0.6721	0.123*
H23B	0.2831	−0.5160	0.6444	0.123*
H23C	0.1658	−0.4807	0.6123	0.123*
H5A	0.172 (4)	−0.335 (6)	0.7048 (10)	0.161 (19)*

	U11	U22	U33	U12	U13	U23
Cu1	0.02835 (13)	0.03863 (14)	0.02980 (13)	0.00368 (8)	0.00441 (8)	0.00103 (8)
Na1	0.0472 (4)	0.0560 (5)	0.0399 (4)	−0.0035 (4)	0.0041 (3)	0.0006 (4)
N1	0.0334 (8)	0.0340 (8)	0.0302 (8)	−0.0024 (6)	0.0040 (6)	0.0005 (6)
N2	0.0304 (7)	0.0360 (8)	0.0364 (8)	−0.0001 (6)	0.0008 (6)	0.0012 (6)
O1	0.0527 (8)	0.0636 (9)	0.0337 (7)	0.0093 (7)	0.0017 (6)	0.0075 (7)
O2	0.0328 (6)	0.0442 (7)	0.0327 (6)	0.0075 (5)	0.0062 (5)	0.0032 (5)
O3	0.0327 (6)	0.0502 (7)	0.0337 (7)	0.0075 (6)	0.0069 (5)	−0.0006 (6)
O4	0.0513 (9)	0.0869 (12)	0.0361 (7)	0.0088 (8)	0.0126 (6)	−0.0058 (8)
O5	0.0989 (15)	0.0591 (11)	0.0731 (13)	−0.0056 (10)	0.0331 (11)	0.0029 (10)
Cl1	0.0488 (3)	0.1063 (5)	0.0580 (3)	−0.0131 (3)	0.0121 (3)	−0.0248 (4)
C1	0.0759 (17)	0.0821 (18)	0.0401 (12)	0.0095 (14)	−0.0066 (11)	0.0158 (12)
C2	0.0365 (9)	0.0344 (9)	0.0361 (9)	−0.0024 (7)	−0.0001 (7)	−0.0008 (7)
C3	0.0361 (9)	0.0351 (9)	0.0506 (11)	0.0030 (8)	−0.0073 (8)	0.0010 (8)
C4	0.0317 (9)	0.0386 (10)	0.0580 (12)	0.0041 (8)	0.0054 (8)	−0.0057 (9)
C5	0.0340 (9)	0.0352 (9)	0.0463 (11)	−0.0007 (7)	0.0104 (8)	−0.0040 (8)
C6	0.0309 (8)	0.0287 (8)	0.0381 (9)	−0.0024 (7)	0.0059 (7)	−0.0036 (7)
C7	0.0292 (8)	0.0284 (8)	0.0349 (9)	−0.0024 (7)	0.0015 (7)	−0.0024 (7)
C8	0.0343 (9)	0.0343 (9)	0.0323 (9)	−0.0037 (7)	0.0081 (7)	−0.0028 (7)
C9	0.0361 (9)	0.0382 (9)	0.0336 (9)	−0.0056 (8)	0.0000 (7)	0.0024 (8)
C10	0.0486 (12)	0.0625 (13)	0.0356 (10)	0.0021 (10)	0.0063 (9)	0.0027 (10)
C11	0.0619 (14)	0.0848 (17)	0.0345 (11)	−0.0027 (13)	0.0040 (10)	0.0124 (11)
C12	0.0591 (14)	0.0755 (16)	0.0450 (12)	0.0012 (12)	−0.0069 (10)	0.0210 (12)
C13	0.0440 (11)	0.0599 (13)	0.0472 (12)	0.0038 (10)	−0.0029 (9)	0.0123 (10)
C14	0.0352 (9)	0.0388 (10)	0.0372 (9)	−0.0050 (7)	−0.0001 (7)	0.0038 (8)
C15	0.0322 (9)	0.0384 (10)	0.0474 (11)	0.0013 (7)	−0.0018 (8)	0.0050 (8)
C16	0.0293 (9)	0.0369 (9)	0.0516 (11)	−0.0008 (7)	0.0056 (8)	−0.0034 (9)
C17	0.0375 (10)	0.0491 (12)	0.0702 (15)	0.0103 (9)	0.0072 (10)	0.0008 (11)
C18	0.0408 (11)	0.0566 (13)	0.0852 (18)	0.0111 (10)	0.0194 (12)	−0.0115 (13)
C19	0.0432 (11)	0.0598 (13)	0.0627 (14)	−0.0020 (10)	0.0216 (10)	−0.0168 (12)
C20	0.0348 (9)	0.0482 (11)	0.0466 (11)	−0.0054 (8)	0.0102 (8)	−0.0108 (9)
C21	0.0270 (8)	0.0378 (9)	0.0428 (10)	−0.0051 (7)	0.0074 (7)	−0.0071 (8)
C22	0.0670 (15)	0.108 (2)	0.0375 (12)	−0.0051 (15)	0.0183 (11)	−0.0125 (13)
C23	0.083 (2)	0.0695 (19)	0.093 (2)	−0.0177 (15)	0.0020 (18)	−0.0110 (15)

Cu1—O3	1.8947 (13)	C5—C6	1.420 (2)
Cu1—O2	1.9029 (12)	C5—H5	0.9300
Cu1—N1	1.9331 (15)	C6—C7	1.422 (2)
Cu1—N2	1.9472 (15)	C6—C8	1.423 (3)
Cu1—Na1	3.4363 (8)	C8—H8	0.9300
Na1—O5	2.339 (2)	C9—C10	1.396 (3)
Na1—O3	2.4047 (15)	C9—C14	1.402 (3)
Na1—O2	2.4633 (14)	C10—C11	1.381 (3)
Na1—O4	2.5828 (17)	C10—H10	0.9300
Na1—Cl1	2.7279 (10)	C11—C12	1.380 (4)
Na1—O1	2.7392 (17)	C11—H11	0.9300
N1—C8	1.297 (2)	C12—C13	1.376 (3)
N1—C9	1.419 (2)	C12—H12	0.9300
N2—C15	1.295 (2)	C13—C14	1.395 (3)
N2—C14	1.414 (2)	C13—H13	0.9300
O1—C2	1.365 (2)	C15—C16	1.427 (3)
O1—C1	1.429 (3)	C15—H15	0.9300
O2—C7	1.305 (2)	C16—C21	1.409 (3)
O3—C21	1.308 (2)	C16—C17	1.421 (3)
O4—C20	1.356 (3)	C17—C18	1.354 (3)
O4—C22	1.435 (2)	C17—H17	0.9300
O5—C23	1.404 (3)	C18—C19	1.399 (4)
O5—H5A	0.86 (3)	C18—H18	0.9300
C1—H1A	0.9600	C19—C20	1.372 (3)
C1—H1B	0.9600	C19—H19	0.9300
C1—H1C	0.9600	C20—C21	1.428 (3)
C2—C3	1.368 (3)	C22—H22A	0.9600
C2—C7	1.431 (3)	C22—H22B	0.9600
C3—C4	1.405 (3)	C22—H22C	0.9600
C3—H3	0.9300	C23—H23A	0.9600
C4—C5	1.356 (3)	C23—H23B	0.9600
C4—H4	0.9300	C23—H23C	0.9600
O3—Cu1—O2	86.27 (5)	C5—C4—H4	119.9
O3—Cu1—N1	177.46 (6)	C3—C4—H4	119.9
O2—Cu1—N1	94.86 (6)	C4—C5—C6	121.22 (18)
O3—Cu1—N2	94.49 (6)	C4—C5—H5	119.4
O2—Cu1—N2	177.46 (6)	C6—C5—H5	119.4
N1—Cu1—N2	84.47 (6)	C5—C6—C7	119.57 (16)
O3—Cu1—Na1	42.40 (4)	C5—C6—C8	117.21 (16)
O2—Cu1—Na1	44.29 (4)	C7—C6—C8	123.23 (15)
N1—Cu1—Na1	138.39 (5)	O2—C7—C6	125.27 (16)
N2—Cu1—Na1	136.71 (5)	O2—C7—C2	117.55 (16)
O5—Na1—O3	117.28 (7)	C6—C7—C2	117.18 (15)
O5—Na1—O2	116.28 (7)	N1—C8—C6	125.73 (16)
O3—Na1—O2	64.46 (4)	N1—C8—H8	117.1
O5—Na1—O4	86.42 (7)	C6—C8—H8	117.1
O3—Na1—O4	61.32 (5)	C10—C9—C14	119.68 (18)
O2—Na1—O4	125.68 (5)	C10—C9—N1	125.01 (18)
O5—Na1—Cl1	109.09 (6)	C14—C9—N1	115.30 (16)
O3—Na1—Cl1	119.65 (5)	C11—C10—C9	119.6 (2)
O2—Na1—Cl1	124.19 (4)	C11—C10—H10	120.2
O4—Na1—Cl1	86.56 (5)	C9—C10—H10	120.2
O5—Na1—O1	85.27 (7)	C12—C11—C10	120.6 (2)
O3—Na1—O1	123.18 (5)	C12—C11—H11	119.7
O2—Na1—O1	58.89 (4)	C10—C11—H11	119.7
O4—Na1—O1	171.68 (6)	C13—C12—C11	120.4 (2)
Cl1—Na1—O1	96.03 (4)	C13—C12—H12	119.8
O5—Na1—Cu1	125.38 (6)	C11—C12—H12	119.8
O3—Na1—Cu1	32.09 (3)	C12—C13—C14	120.0 (2)
O2—Na1—Cu1	32.65 (3)	C12—C13—H13	120.0
O4—Na1—Cu1	93.39 (4)	C14—C13—H13	120.0
Cl1—Na1—Cu1	125.44 (3)	C13—C14—C9	119.59 (18)
O1—Na1—Cu1	91.53 (4)	C13—C14—N2	125.29 (18)
C8—N1—C9	122.57 (16)	C9—C14—N2	115.12 (16)
C8—N1—Cu1	124.68 (13)	N2—C15—C16	125.98 (18)
C9—N1—Cu1	112.62 (12)	N2—C15—H15	117.0
C15—N2—C14	122.97 (16)	C16—C15—H15	117.0
C15—N2—Cu1	124.58 (13)	C21—C16—C17	119.37 (19)
C14—N2—Cu1	112.45 (11)	C21—C16—C15	123.13 (16)
C2—O1—C1	117.35 (17)	C17—C16—C15	117.50 (19)
C2—O1—Na1	118.69 (11)	C18—C17—C16	121.1 (2)
C1—O1—Na1	123.52 (14)	C18—C17—H17	119.4
C7—O2—Cu1	125.64 (11)	C16—C17—H17	119.4
C7—O2—Na1	128.90 (11)	C17—C18—C19	120.3 (2)
Cu1—O2—Na1	103.06 (5)	C17—C18—H18	119.9
C21—O3—Cu1	126.40 (12)	C19—C18—H18	119.9
C21—O3—Na1	127.68 (12)	C20—C19—C18	120.3 (2)
Cu1—O3—Na1	105.50 (6)	C20—C19—H19	119.8
C20—O4—C22	118.06 (18)	C18—C19—H19	119.8
C20—O4—Na1	121.02 (11)	O4—C20—C19	126.06 (19)
C22—O4—Na1	120.19 (15)	O4—C20—C21	112.95 (16)
C23—O5—Na1	120.05 (18)	C19—C20—C21	121.0 (2)
C23—O5—H5A	107 (3)	O3—C21—C16	125.32 (17)
Na1—O5—H5A	133 (3)	O3—C21—C20	116.79 (17)
O1—C1—H1A	109.5	C16—C21—C20	117.89 (17)
O1—C1—H1B	109.5	O4—C22—H22A	109.5
H1A—C1—H1B	109.5	O4—C22—H22B	109.5
O1—C1—H1C	109.5	H22A—C22—H22B	109.5
H1A—C1—H1C	109.5	O4—C22—H22C	109.5
H1B—C1—H1C	109.5	H22A—C22—H22C	109.5
O1—C2—C3	125.50 (17)	H22B—C22—H22C	109.5
O1—C2—C7	112.95 (15)	O5—C23—H23A	109.5
C3—C2—C7	121.55 (17)	O5—C23—H23B	109.5
C2—C3—C4	120.32 (18)	H23A—C23—H23B	109.5
C2—C3—H3	119.8	O5—C23—H23C	109.5
C4—C3—H3	119.8	H23A—C23—H23C	109.5
C5—C4—C3	120.15 (17)	H23B—C23—H23C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···Cl1i	0.86 (2)	2.34 (2)	3.193 (2)	172 (4)
C10—H10···Cl1ii	0.93	2.82	3.729 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯Cl1i	0.86 (2)	2.34 (2)	3.193 (2)	172 (4)
C10—H10⋯Cl1ii	0.93	2.82	3.729 (2)	165

Symmetry codes: (i) ; (ii) .