Aqua-(dicyanamido)-{μ-6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-i-dyne)]diphenolato}copper(II)sodium(I).

The mol-ecule of the title compound, [CuNa(C(18)H(18)N(2)O(4))(C(2)N(3))(H(2)O)], is almost planar, the maximum deviation from the mol-ecular plane being 0.48 (4) Å. The coordination environment of the Cu(2+) ion is distorted square-planar and it is N(2)O(2)-chelated by the Schiff base ligand. The Na(+) cation has a distorted octahedral environment defined by the four O atoms of the 6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolate ligand, a water ligand and a dicyanamide anion.

Related literature

For chemical background, see: Ohba & Okawa (2000 ▶). For related structures, see: Correia et al. (2005 ▶); Costes et al.(2004 ▶).

Experimental

Crystal data

[CuNa(C18H18N2O4)(C2N3)(H2O)]

M = 496.94

Monoclinic,

a = 7.5974 (14) Å

b = 22.999 (4) Å

c = 12.876 (3) Å

β = 101.986 (4)°

V = 2200.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.05 mm−1

T = 293 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.794, T max = 0.825

11729 measured reflections

4314 independent reflections

2996 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.142

S = 1.03

4314 reflections

291 parameters

54 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011064/hg2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011064/hg2492Isup2.hkl

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

[CuNa(C18H18N2O4)(C2N3)(H2O)]	F(000) = 1020
Mr = 496.94	Dx = 1.500 Mg m−3Dm = 1.500 Mg m−3Dm measured by not measured
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3562 reflections
a = 7.5974 (14) Å	θ = 2.8–25.0°
b = 22.999 (4) Å	µ = 1.05 mm−1
c = 12.876 (3) Å	T = 293 K
β = 101.986 (4)°	Block, blue
V = 2200.7 (7) Å3	0.23 × 0.21 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4314 independent reflections
Radiation source: fine-focus sealed tube	2996 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→8
Tmin = 0.794, Tmax = 0.825	k = −27→28
11729 measured reflections	l = −15→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0747P)2 + 0.4736P] where P = (Fo2 + 2Fc2)/3
4314 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.41 e Å−3
54 restraints	Δρmin = −0.49 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	0.24890 (6)	0.506744 (19)	0.06032 (4)	0.04808 (19)
Na1	0.36641 (19)	0.38275 (6)	0.20334 (11)	0.0492 (4)
O1	0.2721 (4)	0.48218 (10)	0.1952 (2)	0.0513 (6)
O2	0.3153 (4)	0.42658 (12)	0.3689 (2)	0.0705 (8)
O3	0.3315 (3)	0.43211 (10)	0.03987 (18)	0.0472 (6)
O4	0.4284 (4)	0.32308 (11)	0.0497 (2)	0.0619 (7)
O5	0.1622 (4)	0.30926 (12)	0.2164 (2)	0.0690 (8)
H5B	0.1286	0.2876	0.1668	0.083*
H5A	0.1030	0.3044	0.2614	0.083*
N1	0.1661 (4)	0.58079 (13)	0.0845 (3)	0.0549 (8)
N2	0.2233 (4)	0.52876 (15)	−0.0761 (3)	0.0556 (8)
N3	0.9191 (5)	0.2881 (2)	0.3649 (3)	0.0874 (10)
N4	0.6425 (6)	0.3426 (2)	0.2955 (3)	0.0896 (11)
N5	1.0355 (6)	0.26675 (19)	0.5447 (3)	0.0868 (12)
C1	0.1804 (5)	0.57156 (17)	0.2676 (4)	0.0603 (11)
C2	0.2396 (5)	0.51238 (16)	0.2741 (3)	0.0492 (9)
C3	0.2601 (6)	0.48344 (18)	0.3710 (3)	0.0592 (10)
C4	0.2247 (7)	0.5129 (2)	0.4559 (4)	0.0818 (15)
H4	0.2371	0.4938	0.5207	0.098*
C5	0.1700 (8)	0.5713 (3)	0.4488 (5)	0.0953 (17)
H5	0.1493	0.5903	0.5089	0.114*
C6	0.1479 (7)	0.5995 (2)	0.3589 (4)	0.0807 (14)
H6	0.1105	0.6381	0.3553	0.097*
C7	0.1477 (6)	0.60141 (17)	0.1718 (4)	0.0656 (12)
H7	0.1090	0.6398	0.1724	0.079*
C8	0.3386 (8)	0.3935 (2)	0.4617 (3)	0.0885 (16)
H8A	0.4210	0.4129	0.5175	0.133*
H8B	0.3861	0.3560	0.4494	0.133*
H8C	0.2248	0.3887	0.4820	0.133*
C9	0.3045 (5)	0.4367 (2)	−0.1448 (3)	0.0630 (11)
C10	0.3413 (5)	0.40704 (17)	−0.0485 (3)	0.0482 (9)
C11	0.3903 (5)	0.34713 (18)	−0.0474 (3)	0.0575 (10)
C12	0.4003 (7)	0.3185 (2)	−0.1381 (4)	0.0846 (15)
H12	0.4310	0.2794	−0.1364	0.101*
C13	0.3647 (9)	0.3482 (4)	−0.2317 (5)	0.112 (2)
H13	0.3715	0.3289	−0.2943	0.134*
C14	0.3192 (8)	0.4058 (3)	−0.2353 (4)	0.0973 (18)
H14	0.2974	0.4249	−0.3004	0.117*
C15	0.2507 (5)	0.4971 (2)	−0.1515 (3)	0.0637 (12)
H15	0.2347	0.5145	−0.2181	0.076*
C16	0.4985 (7)	0.26442 (18)	0.0605 (4)	0.0851 (15)
H16A	0.4074	0.2379	0.0260	0.128*
H16B	0.5331	0.2547	0.1345	0.128*
H16C	0.6014	0.2618	0.0283	0.128*
C17	0.1101 (7)	0.6168 (2)	−0.0103 (4)	0.0847 (15)
H17A	−0.0201	0.6196	−0.0281	0.102*
H17B	0.1590	0.6557	0.0029	0.102*
C18	0.1742 (8)	0.5909 (2)	−0.0959 (4)	0.0906 (16)
H18A	0.2789	0.6122	−0.1072	0.109*
H18B	0.0819	0.5939	−0.1602	0.109*
C19	0.7693 (7)	0.3174 (2)	0.3323 (3)	0.0738 (10)
C20	0.9740 (6)	0.2781 (2)	0.4624 (4)	0.0659 (10)

	U11	U22	U33	U12	U13	U23
Cu1	0.0467 (3)	0.0467 (3)	0.0492 (3)	−0.0028 (2)	0.0064 (2)	0.0091 (2)
Na1	0.0568 (9)	0.0453 (8)	0.0444 (8)	0.0046 (7)	0.0079 (6)	0.0042 (6)
O1	0.0734 (18)	0.0380 (13)	0.0434 (14)	0.0046 (12)	0.0140 (12)	0.0000 (11)
O2	0.115 (3)	0.0577 (17)	0.0409 (15)	0.0092 (17)	0.0201 (15)	0.0046 (13)
O3	0.0575 (15)	0.0475 (14)	0.0362 (13)	0.0008 (12)	0.0090 (11)	0.0018 (11)
O4	0.0793 (19)	0.0461 (15)	0.0653 (19)	0.0003 (13)	0.0264 (15)	−0.0075 (13)
O5	0.088 (2)	0.0678 (18)	0.0566 (17)	−0.0200 (16)	0.0264 (15)	−0.0101 (14)
N1	0.0471 (18)	0.0396 (17)	0.074 (2)	−0.0016 (14)	0.0039 (16)	0.0128 (16)
N2	0.0464 (18)	0.063 (2)	0.053 (2)	−0.0063 (15)	0.0016 (15)	0.0218 (17)
N3	0.076 (2)	0.125 (2)	0.0618 (19)	0.0281 (19)	0.0156 (17)	0.0111 (19)
N4	0.077 (2)	0.121 (3)	0.065 (2)	0.025 (2)	0.0029 (17)	0.0089 (19)
N5	0.097 (3)	0.087 (3)	0.071 (2)	0.019 (2)	0.003 (2)	0.015 (2)
C1	0.056 (2)	0.050 (2)	0.072 (3)	0.0021 (19)	0.008 (2)	−0.019 (2)
C2	0.051 (2)	0.047 (2)	0.050 (2)	−0.0018 (17)	0.0113 (17)	−0.0081 (17)
C3	0.065 (3)	0.065 (3)	0.049 (2)	−0.002 (2)	0.0145 (19)	−0.011 (2)
C4	0.095 (4)	0.104 (4)	0.047 (3)	0.000 (3)	0.015 (2)	−0.017 (2)
C5	0.113 (4)	0.098 (4)	0.076 (4)	0.009 (4)	0.024 (3)	−0.043 (3)
C6	0.083 (3)	0.068 (3)	0.089 (4)	0.016 (3)	0.015 (3)	−0.031 (3)
C7	0.061 (3)	0.037 (2)	0.093 (4)	0.0035 (19)	0.003 (2)	−0.006 (2)
C8	0.126 (4)	0.097 (4)	0.046 (3)	0.000 (3)	0.026 (3)	0.019 (2)
C9	0.044 (2)	0.102 (4)	0.043 (2)	−0.003 (2)	0.0081 (17)	−0.002 (2)
C10	0.040 (2)	0.068 (2)	0.037 (2)	−0.0084 (18)	0.0090 (15)	−0.0053 (18)
C11	0.055 (2)	0.066 (3)	0.056 (3)	−0.010 (2)	0.0186 (19)	−0.019 (2)
C12	0.089 (4)	0.091 (4)	0.075 (3)	−0.002 (3)	0.022 (3)	−0.031 (3)
C13	0.119 (5)	0.160 (6)	0.059 (4)	0.019 (5)	0.024 (3)	−0.037 (4)
C14	0.099 (4)	0.158 (6)	0.036 (3)	0.007 (4)	0.017 (2)	−0.008 (3)
C15	0.048 (2)	0.101 (4)	0.040 (2)	−0.006 (2)	0.0053 (18)	0.019 (2)
C16	0.110 (4)	0.044 (2)	0.109 (4)	−0.001 (2)	0.041 (3)	−0.011 (2)
C17	0.079 (3)	0.074 (3)	0.099 (4)	0.016 (3)	0.014 (3)	0.046 (3)
C18	0.109 (4)	0.079 (3)	0.079 (4)	0.001 (3)	0.009 (3)	0.036 (3)
C19	0.069 (2)	0.103 (3)	0.0486 (19)	0.016 (2)	0.0115 (18)	0.0103 (19)
C20	0.062 (2)	0.082 (2)	0.0536 (19)	0.0124 (18)	0.0107 (17)	0.0120 (19)

Cu1—O1	1.799 (2)	C3—C4	1.360 (6)
Cu1—N2	1.800 (3)	C4—C5	1.404 (7)
Cu1—N1	1.864 (3)	C4—H4	0.9300
Cu1—O3	1.865 (2)	C5—C6	1.306 (7)
Na1—O5	2.324 (3)	C5—H5	0.9300
Na1—O3	2.357 (3)	C6—H6	0.9300
Na1—N4	2.373 (4)	C7—H7	0.9300
Na1—O1	2.392 (3)	C8—H8A	0.9600
Na1—O2	2.461 (3)	C8—H8B	0.9600
Na1—O4	2.531 (3)	C8—H8C	0.9600
O1—C2	1.297 (4)	C9—C14	1.389 (7)
O2—C3	1.375 (5)	C9—C10	1.392 (5)
O2—C8	1.397 (5)	C9—C15	1.446 (6)
O3—C10	1.292 (4)	C10—C11	1.427 (6)
O4—C11	1.343 (5)	C11—C12	1.356 (6)
O4—C16	1.446 (5)	C12—C13	1.363 (8)
O5—H5B	0.8078	C12—H12	0.9300
O5—H5A	0.8118	C13—C14	1.368 (9)
N1—C7	1.254 (6)	C13—H13	0.9300
N1—C17	1.463 (5)	C14—H14	0.9300
N2—C15	1.264 (5)	C15—H15	0.9300
N2—C18	1.485 (6)	C16—H16A	0.9600
N3—C20	1.260 (5)	C16—H16B	0.9600
N3—C19	1.314 (6)	C16—H16C	0.9600
N4—C19	1.139 (5)	C17—C18	1.426 (7)
N5—C20	1.097 (5)	C17—H17A	0.9700
C1—C7	1.389 (6)	C17—H17B	0.9700
C1—C6	1.406 (6)	C18—H18A	0.9700
C1—C2	1.430 (5)	C18—H18B	0.9700
C2—C3	1.393 (6)
O1—Cu1—N2	177.98 (13)	C6—C5—C4	121.0 (5)
O1—Cu1—N1	95.42 (13)	C6—C5—H5	119.5
N2—Cu1—N1	86.24 (16)	C4—C5—H5	119.5
O1—Cu1—O3	83.04 (10)	C5—C6—C1	120.1 (5)
N2—Cu1—O3	95.30 (14)	C5—C6—H6	120.0
N1—Cu1—O3	178.45 (13)	C1—C6—H6	120.0
O5—Na1—O3	117.51 (11)	N1—C7—C1	125.2 (4)
O5—Na1—N4	102.41 (15)	N1—C7—H7	117.4
O3—Na1—N4	123.91 (13)	C1—C7—H7	117.4
O5—Na1—O1	120.00 (11)	O2—C8—H8A	109.5
O3—Na1—O1	61.53 (9)	O2—C8—H8B	109.5
N4—Na1—O1	128.31 (15)	H8A—C8—H8B	109.5
O5—Na1—O2	90.42 (11)	O2—C8—H8C	109.5
O3—Na1—O2	124.57 (10)	H8A—C8—H8C	109.5
N4—Na1—O2	90.49 (13)	H8B—C8—H8C	109.5
O1—Na1—O2	63.05 (9)	C14—C9—C10	117.4 (5)
O5—Na1—O4	84.12 (10)	C14—C9—C15	120.8 (5)
O3—Na1—O4	64.40 (9)	C10—C9—C15	121.8 (4)
N4—Na1—O4	83.75 (13)	O3—C10—C9	121.9 (4)
O1—Na1—O4	125.91 (10)	O3—C10—C11	119.0 (3)
O2—Na1—O4	171.02 (11)	C9—C10—C11	119.1 (4)
C2—O1—Cu1	126.3 (2)	O4—C11—C12	124.2 (4)
C2—O1—Na1	125.6 (2)	O4—C11—C10	114.4 (3)
Cu1—O1—Na1	108.12 (11)	C12—C11—C10	121.4 (4)
C3—O2—C8	119.1 (3)	C11—C12—C13	118.9 (5)
C3—O2—Na1	120.7 (2)	C11—C12—H12	120.6
C8—O2—Na1	120.2 (3)	C13—C12—H12	120.6
C10—O3—Cu1	128.2 (2)	C12—C13—C14	121.2 (5)
C10—O3—Na1	123.7 (2)	C12—C13—H13	119.4
Cu1—O3—Na1	107.21 (11)	C14—C13—H13	119.4
C11—O4—C16	118.6 (3)	C13—C14—C9	122.1 (5)
C11—O4—Na1	117.7 (2)	C13—C14—H14	119.0
C16—O4—Na1	123.7 (3)	C9—C14—H14	119.0
Na1—O5—H5B	119.8	N2—C15—C9	126.6 (4)
Na1—O5—H5A	128.9	N2—C15—H15	116.7
H5B—O5—H5A	110.5	C9—C15—H15	116.7
C7—N1—C17	117.8 (4)	O4—C16—H16A	109.5
C7—N1—Cu1	126.8 (3)	O4—C16—H16B	109.5
C17—N1—Cu1	115.3 (3)	H16A—C16—H16B	109.5
C15—N2—C18	119.8 (4)	O4—C16—H16C	109.5
C15—N2—Cu1	125.9 (3)	H16A—C16—H16C	109.5
C18—N2—Cu1	114.2 (3)	H16B—C16—H16C	109.5
C20—N3—C19	119.8 (4)	C18—C17—N1	108.8 (4)
C19—N4—Na1	171.6 (5)	C18—C17—H17A	109.9
C7—C1—C6	119.1 (4)	N1—C17—H17A	109.9
C7—C1—C2	121.2 (4)	C18—C17—H17B	109.9
C6—C1—C2	119.6 (4)	N1—C17—H17B	109.9
O1—C2—C3	116.2 (3)	H17A—C17—H17B	108.3
O1—C2—C1	124.9 (4)	C17—C18—N2	112.5 (4)
C3—C2—C1	118.8 (4)	C17—C18—H18A	109.1
C4—C3—O2	126.9 (4)	N2—C18—H18A	109.1
C4—C3—C2	118.5 (4)	C17—C18—H18B	109.1
O2—C3—C2	114.5 (3)	N2—C18—H18B	109.1
C3—C4—C5	121.9 (5)	H18A—C18—H18B	107.8
C3—C4—H4	119.0	N4—C19—N3	174.1 (5)
C5—C4—H4	119.0	N5—C20—N3	173.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N5i	0.81	2.02	2.826 (5)	178
O5—H5A···N3ii	0.81	2.15	2.961 (5)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯N5i	0.81	2.02	2.826 (5)	178
O5—H5A⋯N3ii	0.81	2.15	2.961 (5)	173

Symmetry codes: (i) ; (ii) .