catena-Poly[copper(II)-bis-(μ-2-formyl-6-meth-oxy-phenolato-κO,O:O,O)-[(methanol-κO)sodium]-μ-perchlorato-κO:O'].

In the title heterodinuclear complex, [CuNa(C(8)H(7)O(3))(2)(ClO(4))(CH(3)OH)](n), the Cu(II) ion is five-coordinated by four O atoms from two 2-formyl-6-meth-oxy-phenolate anions and one O atom from a perchlorate anion in a distorted square-pyramidal geometry. The Na(+) ion is six-coordinated by four O atoms from two 2-formyl-6-meth-oxy-phenolate ligands, one O atom of a methanol mol-ecule and one O atom of a perchlorate anion. The perchlorate anions link the Na(+) and Cu(II) ions, forming a chain along [010]. O-H⋯O hydrogen bonds connect the chains. π-π inter-actions are present between the benzene rings [centroid-centroid distances = 3.566 (2) and 3.702 (2) Å]. The O atoms of the perchlorate anion are disordered over two sets of sites, with an occupancy ratio of 0.481 (8):0.519 (8).

Related literature

For related structures, see: Gao et al. (2011 ▶); Lin & Zeng (2006 ▶); Yang et al. (2012 ▶).

Experimental

Crystal data

[CuNa(C8H7O3)2(ClO4)(CH4O)]

M = 520.29

Triclinic,

a = 7.9552 (16) Å

b = 8.9453 (18) Å

c = 15.563 (3) Å

α = 81.27 (3)°

β = 84.24 (3)°

γ = 68.25 (3)°

V = 1015.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.29 mm−1

T = 293 K

0.43 × 0.28 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.610, T max = 0.714

9778 measured reflections

4591 independent reflections

3948 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.108

S = 1.11

4591 reflections

321 parameters

48 restraints

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.59 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000876/hy2501sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000876/hy2501Isup2.hkl

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

[CuNa(C8H7O3)2(ClO4)(CH4O)]	Z = 2
Mr = 520.29	F(000) = 530
Triclinic, P1	Dx = 1.701 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9552 (16) Å	Cell parameters from 8587 reflections
b = 8.9453 (18) Å	θ = 3.0–27.6°
c = 15.563 (3) Å	µ = 1.29 mm−1
α = 81.27 (3)°	T = 293 K
β = 84.24 (3)°	Block, green
γ = 68.25 (3)°	0.43 × 0.28 × 0.28 mm
V = 1015.6 (4) Å3

Rigaku R-AXIS RAPID diffractometer	4591 independent reflections
Radiation source: rotation anode	3948 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.610, Tmax = 0.714	k = −11→11
9778 measured reflections	l = −20→20

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.4273P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
4591 reflections	Δρmax = 0.57 e Å−3
321 parameters	Δρmin = −0.59 e Å−3
48 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (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	Occ. (<1)
C1	0.4762 (3)	0.6763 (3)	0.08377 (17)	0.0364 (5)
C2	0.5719 (4)	0.6802 (4)	0.00596 (19)	0.0458 (6)
H2	0.5263	0.7663	−0.0374	0.055*
C3	0.7386 (4)	0.5555 (4)	−0.0092 (2)	0.0537 (7)
H3	0.8026	0.5604	−0.0623	0.064*
C4	0.8070 (4)	0.4280 (4)	0.0531 (2)	0.0484 (7)
H4	0.9171	0.3459	0.0424	0.058*
C5	0.7105 (3)	0.4198 (3)	0.13468 (17)	0.0374 (5)
C6	0.5417 (3)	0.5456 (3)	0.15163 (16)	0.0341 (5)
C7	0.7836 (3)	0.2828 (3)	0.1967 (2)	0.0433 (6)
H7	0.8926	0.2054	0.1797	0.052*
C8	0.2420 (5)	0.9285 (4)	0.0431 (2)	0.0582 (8)
H8A	0.3249	0.9853	0.0322	0.087*
H8B	0.1275	0.9990	0.0651	0.087*
H8C	0.2256	0.8945	−0.0100	0.087*
C9	0.0881 (3)	0.6812 (3)	0.48246 (16)	0.0332 (5)
C10	0.0140 (3)	0.6796 (3)	0.56545 (18)	0.0401 (6)
H10	−0.0893	0.7658	0.5797	0.048*
C11	0.0922 (4)	0.5491 (4)	0.62961 (18)	0.0451 (6)
H11	0.0403	0.5495	0.6859	0.054*
C12	0.2432 (4)	0.4225 (3)	0.60967 (17)	0.0419 (6)
H12	0.2955	0.3374	0.6526	0.050*
C13	0.3218 (3)	0.4197 (3)	0.52328 (17)	0.0344 (5)
C14	0.2437 (3)	0.5486 (3)	0.45824 (15)	0.0302 (5)
C15	0.4787 (3)	0.2836 (3)	0.50530 (18)	0.0379 (5)
H15	0.5227	0.2051	0.5523	0.046*
C16	−0.1374 (4)	0.9355 (3)	0.4313 (2)	0.0482 (7)
H16A	−0.2361	0.8969	0.4426	0.072*
H16B	−0.1606	1.0157	0.3810	0.072*
H16C	−0.1257	0.9829	0.4807	0.072*
C17	−0.1080 (5)	0.7533 (5)	0.1549 (3)	0.0673 (9)
H17A	0.0087	0.6922	0.1305	0.101*
H17B	−0.1874	0.8128	0.1089	0.101*
H17C	−0.1579	0.6806	0.1903	0.101*
Cl1	0.36690 (9)	1.08254 (8)	0.25272 (5)	0.04494 (18)
Cu1	0.50540 (4)	0.39856 (3)	0.32609 (2)	0.03585 (13)
Na1	0.19514 (14)	0.77412 (13)	0.26850 (7)	0.0424 (3)
O1	0.3134 (3)	0.7898 (2)	0.10574 (13)	0.0450 (4)
O2	0.4454 (2)	0.5493 (2)	0.22418 (12)	0.0426 (4)
O3	0.7213 (3)	0.2523 (2)	0.27085 (13)	0.0456 (5)
O4	0.0270 (2)	0.8028 (2)	0.41576 (13)	0.0429 (4)
O5	0.3060 (2)	0.5559 (2)	0.37745 (11)	0.0372 (4)
O6	0.5644 (2)	0.2566 (2)	0.43425 (13)	0.0424 (4)
O7	−0.0898 (3)	0.8613 (3)	0.20606 (16)	0.0603 (6)
H71	−0.1953	0.9215	0.2223	0.090*
O8	0.313 (2)	0.9655 (12)	0.2973 (6)	0.134 (4)	0.481 (8)
O9	0.3691 (13)	1.1775 (13)	0.3156 (6)	0.090 (3)	0.481 (8)
O10	0.5238 (9)	1.0233 (14)	0.2027 (7)	0.104 (4)	0.481 (8)
O11	0.2316 (12)	1.1649 (14)	0.1896 (6)	0.134 (4)	0.481 (8)
O8'	0.2175 (7)	1.0358 (9)	0.2565 (7)	0.093 (3)	0.519 (8)
O9'	0.3203 (10)	1.2409 (8)	0.2718 (7)	0.086 (3)	0.519 (8)
O10'	0.4646 (19)	1.0763 (15)	0.1746 (6)	0.140 (4)	0.519 (8)
O11'	0.5004 (15)	0.9750 (12)	0.3065 (8)	0.164 (5)	0.519 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0334 (11)	0.0377 (12)	0.0389 (13)	−0.0130 (10)	−0.0007 (10)	−0.0073 (10)
C2	0.0491 (15)	0.0542 (16)	0.0385 (14)	−0.0258 (13)	0.0003 (12)	−0.0023 (12)
C3	0.0503 (16)	0.070 (2)	0.0445 (15)	−0.0287 (15)	0.0133 (13)	−0.0103 (14)
C4	0.0365 (13)	0.0568 (17)	0.0508 (16)	−0.0156 (12)	0.0138 (12)	−0.0175 (13)
C5	0.0322 (11)	0.0395 (13)	0.0410 (14)	−0.0121 (10)	0.0045 (10)	−0.0126 (10)
C6	0.0318 (11)	0.0336 (12)	0.0370 (12)	−0.0113 (10)	0.0014 (10)	−0.0087 (10)
C7	0.0299 (11)	0.0374 (13)	0.0552 (16)	−0.0022 (10)	0.0055 (11)	−0.0140 (12)
C8	0.0620 (19)	0.0440 (16)	0.0535 (18)	−0.0038 (14)	−0.0136 (15)	0.0062 (13)
C9	0.0264 (10)	0.0290 (11)	0.0407 (13)	−0.0062 (9)	0.0004 (9)	−0.0047 (9)
C10	0.0316 (11)	0.0404 (13)	0.0439 (14)	−0.0077 (10)	0.0057 (10)	−0.0111 (11)
C11	0.0447 (14)	0.0531 (16)	0.0359 (13)	−0.0170 (12)	0.0050 (11)	−0.0076 (11)
C12	0.0482 (14)	0.0424 (14)	0.0327 (12)	−0.0156 (12)	−0.0048 (11)	0.0017 (10)
C13	0.0321 (11)	0.0312 (11)	0.0384 (13)	−0.0103 (9)	−0.0040 (10)	−0.0015 (9)
C14	0.0259 (10)	0.0265 (10)	0.0351 (12)	−0.0063 (9)	−0.0003 (9)	−0.0037 (9)
C15	0.0342 (12)	0.0293 (11)	0.0428 (13)	−0.0052 (10)	−0.0073 (10)	0.0053 (10)
C16	0.0365 (13)	0.0316 (13)	0.0631 (18)	0.0043 (11)	−0.0030 (12)	−0.0086 (12)
C17	0.074 (2)	0.075 (2)	0.060 (2)	−0.033 (2)	−0.0058 (18)	−0.0119 (18)
Cl1	0.0447 (3)	0.0444 (4)	0.0470 (4)	−0.0179 (3)	0.0014 (3)	−0.0071 (3)
Cu1	0.03095 (18)	0.02748 (18)	0.0382 (2)	0.00017 (12)	0.00257 (12)	−0.00201 (12)
Na1	0.0378 (5)	0.0354 (5)	0.0444 (6)	−0.0028 (4)	−0.0055 (4)	−0.0013 (4)
O1	0.0428 (10)	0.0383 (10)	0.0424 (10)	−0.0039 (8)	−0.0028 (8)	0.0017 (8)
O2	0.0382 (9)	0.0373 (9)	0.0375 (9)	0.0003 (7)	0.0040 (8)	−0.0005 (7)
O3	0.0391 (9)	0.0340 (9)	0.0501 (11)	0.0003 (8)	0.0036 (8)	−0.0033 (8)
O4	0.0375 (9)	0.0287 (8)	0.0461 (10)	0.0041 (7)	0.0032 (8)	−0.0005 (7)
O5	0.0335 (8)	0.0295 (8)	0.0352 (9)	0.0016 (7)	0.0038 (7)	−0.0006 (7)
O6	0.0392 (9)	0.0285 (9)	0.0461 (10)	0.0017 (7)	−0.0020 (8)	−0.0006 (7)
O7	0.0401 (10)	0.0648 (14)	0.0727 (15)	−0.0083 (10)	−0.0068 (10)	−0.0239 (12)
O8	0.216 (9)	0.107 (6)	0.119 (6)	−0.117 (6)	−0.013 (6)	0.018 (5)
O9	0.090 (5)	0.121 (7)	0.091 (5)	−0.064 (5)	0.026 (4)	−0.064 (5)
O10	0.035 (3)	0.137 (7)	0.124 (7)	0.007 (3)	0.012 (3)	−0.073 (6)
O11	0.100 (5)	0.169 (8)	0.097 (5)	−0.007 (5)	−0.034 (4)	−0.001 (5)
O8'	0.046 (3)	0.078 (4)	0.174 (7)	−0.031 (3)	0.009 (3)	−0.059 (5)
O9'	0.059 (3)	0.049 (3)	0.157 (7)	−0.021 (3)	0.013 (4)	−0.038 (4)
O10'	0.193 (10)	0.154 (8)	0.071 (5)	−0.077 (7)	0.044 (6)	−0.005 (5)
O11'	0.165 (7)	0.126 (6)	0.171 (7)	−0.033 (5)	−0.086 (6)	0.073 (6)

C1—O1	1.367 (3)	C16—O4	1.432 (3)
C1—C2	1.367 (4)	C16—H16A	0.9600
C1—C6	1.427 (4)	C16—H16B	0.9600
C2—C3	1.407 (4)	C16—H16C	0.9600
C2—H2	0.9300	C17—O7	1.396 (4)
C3—C4	1.360 (5)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.422 (4)	C17—H17C	0.9600
C4—H4	0.9300	Cl1—O8	1.347 (7)
C5—C7	1.413 (4)	Cl1—O10	1.373 (7)
C5—C6	1.428 (3)	Cl1—O10'	1.373 (9)
C6—O2	1.297 (3)	Cl1—O11'	1.390 (8)
C7—O3	1.242 (3)	Cl1—O8'	1.392 (5)
C7—H7	0.9300	Cl1—O9	1.395 (8)
C8—O1	1.426 (3)	Cl1—O9'	1.396 (7)
C8—H8A	0.9600	Cl1—O11	1.439 (8)
C8—H8B	0.9600	Cu1—O5	1.8890 (18)
C8—H8C	0.9600	Cu1—O2	1.8941 (19)
C9—C10	1.365 (4)	Cu1—O6	1.932 (2)
C9—O4	1.365 (3)	Cu1—O3	1.944 (2)
C9—C14	1.426 (3)	Cu1—O9i	2.614 (11)
C10—C11	1.407 (4)	Cu1—O9'i	2.650 (8)
C10—H10	0.9300	Cu1—Na1	3.4010 (17)
C11—C12	1.358 (4)	Na1—O5	2.342 (2)
C11—H11	0.9300	Na1—O8	2.349 (9)
C12—C13	1.424 (4)	Na1—O7	2.365 (2)
C12—H12	0.9300	Na1—O2	2.379 (2)
C13—C14	1.408 (3)	Na1—O8'	2.390 (7)
C13—C15	1.423 (3)	Na1—O4	2.533 (2)
C14—O5	1.306 (3)	Na1—O1	2.614 (2)
C15—O6	1.246 (3)	O7—H71	0.8500
C15—H15	0.9300
O1—C1—C2	125.9 (3)	O11'—Cl1—O8'	111.4 (6)
O1—C1—C6	113.0 (2)	O8—Cl1—O9	104.4 (6)
C2—C1—C6	121.1 (2)	O10—Cl1—O9	116.6 (6)
C1—C2—C3	120.7 (3)	O10'—Cl1—O9'	105.4 (7)
C1—C2—H2	119.6	O11'—Cl1—O9'	110.6 (6)
C3—C2—H2	119.6	O8'—Cl1—O9'	112.5 (4)
C4—C3—C2	120.5 (3)	O8—Cl1—O11	104.6 (7)
C4—C3—H3	119.7	O10—Cl1—O11	103.6 (6)
C2—C3—H3	119.7	O9—Cl1—O11	113.9 (6)
C3—C4—C5	120.1 (3)	O5—Cu1—O2	83.82 (8)
C3—C4—H4	119.9	O5—Cu1—O6	93.45 (8)
C5—C4—H4	119.9	O2—Cu1—O6	176.21 (8)
C7—C5—C4	118.3 (2)	O5—Cu1—O3	174.49 (8)
C7—C5—C6	121.4 (2)	O2—Cu1—O3	93.50 (9)
C4—C5—C6	120.2 (3)	O6—Cu1—O3	89.00 (8)
O2—C6—C1	118.2 (2)	O2—Cu1—O9i	107.1 (2)
O2—C6—C5	124.5 (2)	O3—Cu1—O9i	84.5 (2)
C1—C6—C5	117.2 (2)	O5—Cu1—O9i	100.9 (2)
O3—C7—C5	128.4 (2)	O6—Cu1—O9i	75.9 (2)
O3—C7—H7	115.8	O2—Cu1—O9'i	88.9 (2)
C5—C7—H7	115.8	O3—Cu1—O9'i	87.86 (19)
O1—C8—H8A	109.5	O5—Cu1—O9'i	96.87 (19)
O1—C8—H8B	109.5	O6—Cu1—O9'i	94.0 (2)
H8A—C8—H8B	109.5	O5—Na1—O8	104.4 (3)
O1—C8—H8C	109.5	O5—Na1—O7	126.05 (9)
H8A—C8—H8C	109.5	O8—Na1—O7	120.1 (3)
H8B—C8—H8C	109.5	O5—Na1—O2	64.72 (7)
C10—C9—O4	125.8 (2)	O8—Na1—O2	106.8 (4)
C10—C9—C14	120.8 (2)	O7—Na1—O2	121.84 (9)
O4—C9—C14	113.4 (2)	O5—Na1—O8'	127.7 (2)
C9—C10—C11	120.7 (2)	O8—Na1—O8'	24.3 (3)
C9—C10—H10	119.6	O7—Na1—O8'	96.63 (19)
C11—C10—H10	119.6	O2—Na1—O8'	120.27 (15)
C12—C11—C10	120.3 (2)	O5—Na1—O4	63.79 (7)
C12—C11—H11	119.9	O8—Na1—O4	87.9 (3)
C10—C11—H11	119.9	O7—Na1—O4	87.65 (8)
C11—C12—C13	120.2 (2)	O2—Na1—O4	128.46 (8)
C11—C12—H12	119.9	O8'—Na1—O4	93.2 (2)
C13—C12—H12	119.9	O5—Na1—O1	126.62 (8)
C14—C13—C15	121.7 (2)	O8—Na1—O1	92.0 (3)
C14—C13—C12	120.1 (2)	O7—Na1—O1	82.97 (9)
C15—C13—C12	118.2 (2)	O2—Na1—O1	61.92 (7)
O5—C14—C13	124.3 (2)	O8'—Na1—O1	82.4 (2)
O5—C14—C9	117.9 (2)	O4—Na1—O1	169.07 (7)
C13—C14—C9	117.9 (2)	C1—O1—C8	116.7 (2)
O6—C15—C13	128.0 (2)	C1—O1—Na1	118.00 (15)
O6—C15—H15	116.0	C8—O1—Na1	123.66 (18)
C13—C15—H15	116.0	C6—O2—Cu1	127.00 (16)
O4—C16—H16A	109.5	C6—O2—Na1	126.71 (16)
O4—C16—H16B	109.5	Cu1—O2—Na1	104.90 (9)
H16A—C16—H16B	109.5	C7—O3—Cu1	124.61 (17)
O4—C16—H16C	109.5	C9—O4—C16	117.8 (2)
H16A—C16—H16C	109.5	C9—O4—Na1	118.86 (14)
H16B—C16—H16C	109.5	C16—O4—Na1	123.15 (17)
O7—C17—H17A	109.5	C14—O5—Cu1	127.46 (15)
O7—C17—H17B	109.5	C14—O5—Na1	125.99 (14)
H17A—C17—H17B	109.5	Cu1—O5—Na1	106.52 (8)
O7—C17—H17C	109.5	C15—O6—Cu1	125.08 (16)
H17A—C17—H17C	109.5	C17—O7—Na1	114.4 (2)
H17B—C17—H17C	109.5	C17—O7—H71	108.0
O8—Cl1—O10	113.3 (8)	Na1—O7—H71	132.5
O10'—Cl1—O11'	100.0 (8)	Cl1—O8—Na1	138.4 (7)
O10'—Cl1—O8'	116.1 (7)	Cl1—O8'—Na1	131.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H71···O10ii	0.85	2.11	2.874 (7)	149
O7—H71···O11'ii	0.85	2.55	3.334 (13)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H71⋯O10i	0.85	2.11	2.874 (7)	149
O7—H71⋯O11′i	0.85	2.55	3.334 (13)	154

Symmetry code: (i) .