{μ-6,6'-Dimeth-oxy-2,2'-[ethane-1,2-diyl-bis(nitrilo-methyl-idyne)]diphenolato-1κO,O,O,O:2κO,N,N',O}(methanol-1κO)(perchlorato-1κO)nickel(II)sodium.

The mol-ecule of the title compound, [NaNi(C(18)H(18)N(2)O(4))(ClO(4))(CH(3)OH)], is almost planar, the maximum deviation from the molecular plane being 5.3 (1) Å. The Ni(2+) ion is N(2)O(2) coordinated by the Schiff base ligand, leading to a slightly distorted square-planar environment. The Na atom is chelated by the four O atoms of the Schiff base ligand and is coordinated by the O atoms of a methanol ligand and a perchlorate anion. The perchlorate ion is disordered over two sites with occupancies 0.723 (12):0.277 (12).

Related literature

For background to Schiff bases as ligands for metal ions and their roles in biochemical processes, see: Lindoy et al. (1976 ▶). For the steric, electronic and lipophilic properties of N,N-disalicylideneethyl­enediamine type Schiff bases ligands, see: Correia et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[NaNi(C18H18N2O4)(n class="Chemical">ClO4)(CH4O)]

M = 539.54

Monoclinic,

a = 12.026 (2) Å

b = 8.1360 (16) Å

c = 23.394 (5) Å

β = 104.302 (3)°

V = 2218.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.07 mm−1

T = 273 K

0.14 × 0.12 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.865, T max = 0.892

10559 measured reflections

3906 independent reflections

3120 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.159

S = 1.06

3906 reflections

339 parameters

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −1.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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/S1600536809007776/hg2479sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007776/hg2479Isup2.hkl

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

[NaNi(C18H18N2O4)(ClO4)(CH4O)]	F(000) = 1111.9
Mr = 539.54	Dx = 1.616 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3601 reflections
a = 12.026 (2) Å	θ = 2.7–26.6°
b = 8.1360 (16) Å	µ = 1.07 mm−1
c = 23.394 (5) Å	T = 273 K
β = 104.302 (3)°	Block, orange
V = 2218.0 (8) Å3	0.14 × 0.12 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3906 independent reflections
Radiation source: fine-focus sealed tube	3120 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→14
Tmin = 0.865, Tmax = 0.892	k = −9→9
10559 measured reflections	l = −27→27

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0852P)2 + 3.4175P] where P = (Fo2 + 2Fc2)/3
3906 reflections	(Δ/σ)max = 0.001
339 parameters	Δρmax = 1.03 e Å−3
0 restraints	Δρmin = −1.14 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	Occ. (<1)
Ni1	0.17531 (4)	0.91320 (6)	1.01069 (2)	0.0373 (2)
Na1	0.14961 (15)	0.9105 (2)	0.86470 (7)	0.0501 (5)
Cl1	0.00049 (13)	1.1323 (2)	0.73545 (7)	0.0721 (4)
O1	0.2467 (2)	1.0034 (4)	0.95724 (11)	0.0448 (7)
O2	0.0756 (2)	0.8289 (4)	0.94440 (12)	0.0447 (7)
O3	0.3169 (3)	1.0958 (4)	0.86647 (14)	0.0576 (9)
O4	−0.0318 (3)	0.7296 (4)	0.84088 (13)	0.0557 (8)
O5	−0.0995 (6)	1.2219 (13)	0.7369 (3)	0.102 (3)	0.723 (12)
O6	0.0663 (7)	1.2518 (12)	0.7120 (4)	0.104 (3)	0.723 (12)
O7	−0.0350 (8)	1.0008 (11)	0.6966 (4)	0.128 (4)	0.723 (12)
O8	0.0599 (6)	1.0976 (10)	0.7922 (4)	0.090 (3)	0.723 (12)
O5'	0.0360 (19)	1.150 (3)	0.6850 (10)	0.102 (7)	0.277 (12)
O6'	−0.1060 (17)	1.082 (3)	0.7329 (9)	0.098 (7)	0.277 (12)
O7'	0.0321 (18)	1.264 (3)	0.7734 (10)	0.118 (9)	0.277 (12)
O8'	0.0764 (13)	1.002 (2)	0.7645 (8)	0.076 (5)	0.277 (12)
O9	0.2372 (3)	0.6892 (5)	0.83487 (16)	0.0696 (10)
H9A	0.2928	0.6982	0.8209	0.12 (3)*
N1	0.2807 (3)	0.9918 (5)	1.07592 (14)	0.0457 (9)
N2	0.0964 (3)	0.8305 (5)	1.06239 (15)	0.0458 (9)
C1	0.3996 (4)	1.1441 (5)	1.02507 (19)	0.0441 (10)
C2	0.3391 (3)	1.0965 (5)	0.96838 (19)	0.0398 (9)
C3	0.3795 (4)	1.1522 (5)	0.91995 (19)	0.0435 (10)
C4	0.4748 (4)	1.2522 (6)	0.9279 (2)	0.0552 (12)
H4	0.5003	1.2882	0.8956	0.066*
C5	0.5326 (4)	1.2990 (6)	0.9852 (2)	0.0590 (12)
H5	0.5965	1.3672	0.9908	0.071*
C6	0.4969 (4)	1.2463 (6)	1.0322 (2)	0.0560 (12)
H6	0.5368	1.2776	1.0699	0.067*
C7	0.3659 (4)	1.0869 (6)	1.0762 (2)	0.0486 (11)
H7	0.4096	1.1216	1.1127	0.058*
C8	0.3589 (5)	1.1308 (8)	0.8156 (2)	0.0695 (15)
H8A	0.3547	1.2470	0.8082	0.104*
H8B	0.3130	1.0738	0.7821	0.104*
H8C	0.4372	1.0952	0.8225	0.104*
C9	−0.0578 (4)	0.6982 (5)	0.99182 (19)	0.0443 (10)
C10	−0.0165 (3)	0.7390 (5)	0.94207 (18)	0.0409 (9)
C11	−0.0784 (4)	0.6823 (6)	0.8863 (2)	0.0455 (10)
C12	−0.1784 (4)	0.5926 (6)	0.8798 (2)	0.0562 (12)
H12	−0.2192	0.5578	0.8427	0.067*
C13	−0.2176 (4)	0.5547 (6)	0.9300 (3)	0.0593 (13)
H13	−0.2844	0.4934	0.9260	0.071*
C14	−0.1599 (4)	0.6058 (6)	0.9838 (2)	0.0555 (13)
H14	−0.1878	0.5798	1.0164	0.067*
C15	0.0024 (4)	0.7488 (6)	1.0494 (2)	0.0506 (11)
H15	−0.0294	0.7200	1.0804	0.061*
C16	−0.0870 (5)	0.6700 (9)	0.7830 (2)	0.0777 (17)
H16A	−0.0888	0.5520	0.7834	0.117*
H16B	−0.0451	0.7064	0.7553	0.117*
H16C	−0.1640	0.7117	0.7715	0.117*
C17	0.2655 (5)	0.9255 (7)	1.1318 (2)	0.0665 (15)
H17A	0.2888	1.0066	1.1629	0.080*
H17B	0.3126	0.8282	1.1428	0.080*
C18	0.1423 (5)	0.8834 (7)	1.1241 (2)	0.0668 (15)
H18A	0.1345	0.7955	1.1509	0.080*
H18B	0.1003	0.9784	1.1326	0.080*
C19	0.2246 (7)	0.5342 (9)	0.8564 (4)	0.106 (2)
H19A	0.2947	0.5023	0.8838	0.159*
H19B	0.2069	0.4572	0.8244	0.159*
H19C	0.1634	0.5353	0.8761	0.159*

	U11	U22	U33	U12	U13	U23
Ni1	0.0411 (3)	0.0449 (3)	0.0281 (3)	0.0071 (2)	0.0126 (2)	0.0040 (2)
Na1	0.0508 (10)	0.0657 (12)	0.0362 (9)	0.0019 (8)	0.0151 (7)	0.0012 (8)
Cl1	0.0655 (9)	0.0880 (11)	0.0692 (9)	0.0145 (8)	0.0287 (7)	0.0277 (8)
O1	0.0419 (16)	0.0623 (19)	0.0320 (14)	−0.0024 (14)	0.0123 (12)	0.0025 (14)
O2	0.0444 (16)	0.0592 (19)	0.0349 (15)	−0.0049 (14)	0.0179 (12)	0.0009 (13)
O3	0.0554 (19)	0.080 (2)	0.0412 (17)	−0.0055 (17)	0.0197 (15)	0.0096 (16)
O4	0.0533 (18)	0.071 (2)	0.0439 (17)	−0.0065 (16)	0.0147 (14)	−0.0040 (16)
O5	0.088 (5)	0.121 (7)	0.094 (5)	0.030 (5)	0.017 (4)	−0.005 (5)
O6	0.101 (5)	0.116 (7)	0.101 (6)	−0.012 (5)	0.036 (5)	0.032 (5)
O7	0.136 (7)	0.116 (7)	0.125 (7)	0.020 (6)	0.016 (6)	−0.007 (6)
O8	0.081 (4)	0.105 (7)	0.077 (5)	0.005 (4)	0.008 (3)	0.025 (4)
O5'	0.097 (15)	0.12 (2)	0.091 (15)	0.004 (14)	0.027 (11)	0.013 (13)
O6'	0.087 (13)	0.115 (18)	0.090 (13)	0.003 (12)	0.020 (10)	0.012 (12)
O7'	0.112 (15)	0.123 (18)	0.112 (17)	0.006 (13)	0.015 (12)	0.003 (14)
O8'	0.072 (9)	0.088 (12)	0.067 (10)	0.006 (9)	0.015 (8)	0.010 (9)
O9	0.067 (2)	0.082 (3)	0.064 (2)	0.010 (2)	0.0246 (19)	−0.003 (2)
N1	0.051 (2)	0.055 (2)	0.0295 (17)	0.0113 (18)	0.0066 (15)	0.0046 (16)
N2	0.061 (2)	0.048 (2)	0.0331 (18)	0.0052 (18)	0.0199 (16)	0.0049 (16)
C1	0.044 (2)	0.044 (2)	0.043 (2)	0.0100 (19)	0.0077 (18)	0.0011 (19)
C2	0.036 (2)	0.040 (2)	0.043 (2)	0.0075 (17)	0.0101 (17)	0.0023 (18)
C3	0.042 (2)	0.045 (2)	0.044 (2)	0.0079 (19)	0.0119 (18)	0.0065 (19)
C4	0.052 (3)	0.047 (3)	0.072 (3)	0.004 (2)	0.024 (2)	0.013 (2)
C5	0.053 (3)	0.048 (3)	0.075 (3)	−0.006 (2)	0.013 (2)	0.000 (2)
C6	0.055 (3)	0.049 (3)	0.059 (3)	−0.003 (2)	0.005 (2)	−0.008 (2)
C7	0.050 (3)	0.054 (3)	0.037 (2)	0.007 (2)	0.0025 (19)	−0.0044 (19)
C8	0.075 (4)	0.093 (4)	0.049 (3)	−0.007 (3)	0.032 (3)	0.012 (3)
C9	0.046 (2)	0.045 (2)	0.048 (2)	0.0090 (19)	0.0224 (19)	0.0110 (19)
C10	0.039 (2)	0.042 (2)	0.046 (2)	0.0068 (18)	0.0190 (18)	0.0045 (19)
C11	0.039 (2)	0.051 (3)	0.049 (2)	0.0013 (19)	0.0151 (19)	0.002 (2)
C12	0.048 (3)	0.057 (3)	0.063 (3)	0.001 (2)	0.013 (2)	0.000 (2)
C13	0.045 (3)	0.061 (3)	0.078 (4)	−0.006 (2)	0.027 (3)	0.006 (3)
C14	0.051 (3)	0.056 (3)	0.069 (3)	0.007 (2)	0.034 (3)	0.014 (2)
C15	0.061 (3)	0.054 (3)	0.047 (3)	0.010 (2)	0.034 (2)	0.012 (2)
C16	0.080 (4)	0.106 (5)	0.046 (3)	−0.023 (3)	0.013 (3)	−0.016 (3)
C17	0.077 (4)	0.090 (4)	0.031 (2)	0.002 (3)	0.010 (2)	0.010 (2)
C18	0.092 (4)	0.076 (4)	0.038 (3)	−0.001 (3)	0.028 (3)	0.003 (2)
C19	0.114 (6)	0.092 (5)	0.117 (6)	0.042 (5)	0.038 (5)	0.034 (5)

Ni1—O1	1.836 (3)	C1—C7	1.432 (6)
Ni1—N2	1.840 (4)	C2—C3	1.414 (6)
Ni1—N1	1.841 (4)	C3—C4	1.380 (6)
Ni1—O2	1.843 (3)	C4—C5	1.402 (7)
Ni1—Na1	3.3525 (19)	C4—H4	0.9300
Na1—O9	2.281 (4)	C5—C6	1.346 (7)
Na1—O1	2.318 (3)	C5—H5	0.9300
Na1—O8	2.335 (7)	C6—H6	0.9300
Na1—O2	2.351 (3)	C7—H7	0.9300
Na1—O8'	2.408 (16)	C8—H8A	0.9600
Na1—O3	2.506 (4)	C8—H8B	0.9600
Na1—O4	2.576 (4)	C8—H8C	0.9600
Cl1—O6'	1.33 (2)	C9—C14	1.412 (6)
Cl1—O5'	1.36 (2)	C9—C10	1.413 (6)
Cl1—O8	1.373 (7)	C9—C15	1.423 (7)
Cl1—O7'	1.39 (2)	C10—C11	1.410 (6)
Cl1—O7	1.400 (9)	C11—C12	1.383 (6)
Cl1—O5	1.414 (7)	C12—C13	1.403 (7)
Cl1—O6	1.445 (8)	C12—H12	0.9300
Cl1—O8'	1.456 (17)	C13—C14	1.343 (7)
O1—C2	1.315 (5)	C13—H13	0.9300
O2—C10	1.317 (5)	C14—H14	0.9300
O3—C3	1.370 (5)	C15—H15	0.9300
O3—C8	1.432 (5)	C16—H16A	0.9600
O4—C11	1.374 (5)	C16—H16B	0.9600
O4—C16	1.437 (6)	C16—H16C	0.9600
O9—C19	1.380 (8)	C17—C18	1.488 (8)
O9—H9A	0.8174	C17—H17A	0.9700
N1—C7	1.283 (6)	C17—H17B	0.9700
N1—C17	1.468 (6)	C18—H18A	0.9700
N2—C15	1.281 (6)	C18—H18B	0.9700
N2—C18	1.477 (6)	C19—H19A	0.9600
C1—C2	1.401 (6)	C19—H19B	0.9600
C1—C6	1.411 (7)	C19—H19C	0.9600
O1—Ni1—N2	176.62 (15)	C19—O9—H9A	113.8
O1—Ni1—N1	94.78 (15)	Na1—O9—H9A	122.5
N2—Ni1—N1	86.77 (17)	C7—N1—C17	119.5 (4)
O1—Ni1—O2	83.82 (12)	C7—N1—Ni1	126.8 (3)
N2—Ni1—O2	94.76 (15)	C17—N1—Ni1	113.5 (3)
N1—Ni1—O2	177.16 (14)	C15—N2—C18	118.5 (4)
O1—Ni1—Na1	41.38 (9)	C15—N2—Ni1	127.0 (3)
N2—Ni1—Na1	137.28 (13)	C18—N2—Ni1	114.0 (3)
N1—Ni1—Na1	135.89 (12)	C2—C1—C6	119.8 (4)
O2—Ni1—Na1	42.52 (9)	C2—C1—C7	120.8 (4)
O9—Na1—O1	112.26 (14)	C6—C1—C7	119.3 (4)
O9—Na1—O8	117.3 (3)	O1—C2—C1	124.2 (4)
O1—Na1—O8	120.1 (3)	O1—C2—C3	117.8 (4)
O9—Na1—O2	108.27 (15)	C1—C2—C3	118.0 (4)
O1—Na1—O2	63.49 (11)	O3—C3—C4	124.9 (4)
O8—Na1—O2	124.2 (2)	O3—C3—C2	113.8 (4)
O9—Na1—O8'	91.8 (5)	C4—C3—C2	121.3 (4)
O1—Na1—O8'	141.9 (5)	C3—C4—C5	119.3 (5)
O8—Na1—O8'	25.9 (4)	C3—C4—H4	120.4
O2—Na1—O8'	137.7 (4)	C5—C4—H4	120.4
O9—Na1—O3	92.89 (15)	C6—C5—C4	120.8 (5)
O1—Na1—O3	64.60 (11)	C6—C5—H5	119.6
O8—Na1—O3	81.1 (2)	C4—C5—H5	119.6
O2—Na1—O3	128.05 (13)	C5—C6—C1	120.9 (5)
O8'—Na1—O3	86.0 (4)	C5—C6—H6	119.5
O9—Na1—O4	85.03 (14)	C1—C6—H6	119.5
O1—Na1—O4	126.36 (12)	N1—C7—C1	125.6 (4)
O8—Na1—O4	90.0 (2)	N1—C7—H7	117.2
O2—Na1—O4	62.87 (11)	C1—C7—H7	117.2
O8'—Na1—O4	83.0 (4)	O3—C8—H8A	109.5
O3—Na1—O4	168.75 (13)	O3—C8—H8B	109.5
O9—Na1—Ni1	112.55 (11)	H8A—C8—H8B	109.5
O1—Na1—Ni1	31.57 (7)	O3—C8—H8C	109.5
O8—Na1—Ni1	130.2 (3)	H8A—C8—H8C	109.5
O2—Na1—Ni1	31.98 (8)	H8B—C8—H8C	109.5
O8'—Na1—Ni1	155.4 (5)	C14—C9—C10	119.1 (4)
O3—Na1—Ni1	96.18 (9)	C14—C9—C15	120.1 (4)
O4—Na1—Ni1	94.83 (8)	C10—C9—C15	120.8 (4)
O6'—Cl1—O5'	120.0 (14)	O2—C10—C11	117.8 (4)
O6'—Cl1—O8	104.1 (9)	O2—C10—C9	124.0 (4)
O5'—Cl1—O8	131.5 (10)	C11—C10—C9	118.2 (4)
O6'—Cl1—O7'	112.1 (14)	O4—C11—C12	124.9 (4)
O5'—Cl1—O7'	112.2 (16)	O4—C11—C10	113.6 (4)
O8—Cl1—O7'	62.9 (9)	C12—C11—C10	121.4 (4)
O6'—Cl1—O7	66.4 (11)	C11—C12—C13	119.1 (5)
O5'—Cl1—O7	68.2 (13)	C11—C12—H12	120.4
O8—Cl1—O7	118.2 (5)	C13—C12—H12	120.4
O7'—Cl1—O7	178.2 (9)	C14—C13—C12	120.8 (5)
O6'—Cl1—O5	49.2 (9)	C14—C13—H13	119.6
O5'—Cl1—O5	114.6 (10)	C12—C13—H13	119.6
O8—Cl1—O5	109.0 (5)	C13—C14—C9	121.4 (4)
O7'—Cl1—O5	71.7 (9)	C13—C14—H14	119.3
O7—Cl1—O5	106.6 (5)	C9—C14—H14	119.3
O6'—Cl1—O6	143.3 (10)	N2—C15—C9	125.9 (4)
O5'—Cl1—O6	43.8 (10)	N2—C15—H15	117.0
O8—Cl1—O6	107.6 (5)	C9—C15—H15	117.0
O7'—Cl1—O6	68.4 (10)	O4—C16—H16A	109.5
O7—Cl1—O6	112.1 (6)	O4—C16—H16B	109.5
O5—Cl1—O6	102.1 (6)	H16A—C16—H16B	109.5
O6'—Cl1—O8'	106.3 (12)	O4—C16—H16C	109.5
O5'—Cl1—O8'	100.9 (12)	H16A—C16—H16C	109.5
O8—Cl1—O8'	44.1 (7)	H16B—C16—H16C	109.5
O7'—Cl1—O8'	103.1 (12)	N1—C17—C18	108.5 (4)
O7—Cl1—O8'	78.5 (9)	N1—C17—H17A	110.0
O5—Cl1—O8'	143.6 (7)	C18—C17—H17A	110.0
O6—Cl1—O8'	109.3 (7)	N1—C17—H17B	110.0
C2—O1—Ni1	127.5 (3)	C18—C17—H17B	110.0
C2—O1—Na1	125.4 (3)	H17A—C17—H17B	108.4
Ni1—O1—Na1	107.04 (14)	N2—C18—C17	107.8 (4)
C10—O2—Ni1	127.4 (3)	N2—C18—H18A	110.1
C10—O2—Na1	127.1 (3)	C17—C18—H18A	110.1
Ni1—O2—Na1	105.50 (13)	N2—C18—H18B	110.1
C3—O3—C8	117.7 (4)	C17—C18—H18B	110.1
C3—O3—Na1	118.3 (3)	H18A—C18—H18B	108.5
C8—O3—Na1	123.6 (3)	O9—C19—H19A	109.5
C11—O4—C16	116.9 (4)	O9—C19—H19B	109.5
C11—O4—Na1	118.6 (3)	H19A—C19—H19B	109.5
C16—O4—Na1	124.5 (3)	O9—C19—H19C	109.5
Cl1—O8—Na1	150.8 (6)	H19A—C19—H19C	109.5
Cl1—O8'—Na1	135.7 (13)	H19B—C19—H19C	109.5
C19—O9—Na1	120.6 (4)