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

The mol-ecule of the title compound, [NaNi(C(18)H(18)N(2)O(4))(C(2)N(3))(H(2)O)], is approximately planar, with a maximum deviation from the mol-ecular plane of 0.770 (5) Å. The coordination environment of the Ni(2+) ion is distorted square-planar and it is N(2)O(2) coordinated by the 6,6'-dimeth-oxy-2,2'-[ethane-1,2-diylbis(nitrilo-methyl-idyne)]diphenolate Schiff base ligand. The Na(+) atom is chelated by the four O atoms of the Schiff base ligand, a water ligand and a dicyanamide anion. The structure displays inter-molecular O-H⋯N hydrogen bonding.

Related literature

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

Experimental

Crystal data

[NaNi(C18H18N2O4)(C2N3)(H2O)]

M = 492.11

Monoclinic,

a = 7.4654 (14) Å

b = 22.745 (4) Å

c = 13.177 (3) Å

β = 101.282 (4)°

V = 2194.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.95 mm−1

T = 293 K

0.14 × 0.13 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.879, T max = 0.903

10817 measured reflections

3864 independent reflections

2815 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.02

3864 reflections

291 parameters

54 restraints

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.35 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/S160053680901438X/hg2500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901438X/hg2500Isup2.hkl

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

[NaNi(C18H18N2O4)(C2N3)(H2O)]	F(000) = 1016
Mr = 492.11	Dx = 1.490 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3120 reflections
a = 7.4654 (14) Å	θ = 2.5–24.6°
b = 22.745 (4) Å	µ = 0.95 mm−1
c = 13.177 (3) Å	T = 293 K
β = 101.282 (4)°	Block, orange
V = 2194.2 (8) Å3	0.14 × 0.13 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3864 independent reflections
Radiation source: fine-focus sealed tube	2815 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
Tmin = 0.879, Tmax = 0.903	k = −26→27
10817 measured reflections	l = −15→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.4335P] where P = (Fo2 + 2Fc2)/3
3864 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.33 e Å−3
54 restraints	Δρmin = −0.35 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
Ni1	0.24893 (5)	0.506776 (16)	0.06029 (3)	0.04684 (15)
Na1	0.36614 (16)	0.38280 (5)	0.20328 (9)	0.0527 (3)
O1	0.2723 (3)	0.48215 (8)	0.19509 (16)	0.0545 (5)
O2	0.3315 (3)	0.43203 (8)	0.03988 (15)	0.0497 (5)
O3	0.3154 (4)	0.42650 (10)	0.36882 (17)	0.0732 (7)
O4	0.4284 (3)	0.32315 (9)	0.04958 (19)	0.0655 (6)
O5	0.1624 (3)	0.30933 (10)	0.21624 (17)	0.0731 (7)
H5A	0.1005	0.3032	0.2601	0.088*
H5B	0.1305	0.2871	0.1665	0.088*
N1	0.1665 (3)	0.58076 (11)	0.0844 (2)	0.0584 (7)
N2	0.2232 (3)	0.52892 (13)	−0.0760 (2)	0.0589 (7)
N3	0.9189 (4)	0.28821 (17)	0.3648 (3)	0.0917 (9)
N4	1.0360 (5)	0.26666 (15)	0.5450 (3)	0.0888 (10)
N5	0.6431 (5)	0.34246 (17)	0.2954 (3)	0.0934 (9)
C1	0.3049 (4)	0.43665 (18)	−0.1445 (3)	0.0652 (10)
C2	0.3415 (4)	0.40716 (15)	−0.0485 (2)	0.0511 (8)
C3	0.3908 (4)	0.34689 (15)	−0.0474 (3)	0.0601 (9)
C4	0.4007 (6)	0.3183 (2)	−0.1377 (4)	0.0885 (13)
H4	0.4321	0.2787	−0.1361	0.106*
C5	0.3642 (7)	0.3480 (3)	−0.2315 (4)	0.1134 (17)
H5	0.3708	0.3281	−0.2923	0.136*
C6	0.3189 (6)	0.4060 (3)	−0.2353 (3)	0.0998 (15)
H6	0.2969	0.4256	−0.2985	0.120*
C7	0.2509 (5)	0.49684 (19)	−0.1515 (3)	0.0694 (11)
H7	0.2342	0.5144	−0.2164	0.083*
C8	0.4977 (6)	0.26446 (15)	0.0610 (3)	0.0903 (13)
H8A	0.4044	0.2375	0.0292	0.135*
H8B	0.5337	0.2553	0.1332	0.135*
H8C	0.6014	0.2611	0.0283	0.135*
C9	0.1804 (5)	0.57147 (14)	0.2674 (3)	0.0631 (9)
C10	0.2389 (4)	0.51231 (13)	0.2744 (3)	0.0524 (8)
C11	0.2599 (5)	0.48361 (15)	0.3708 (3)	0.0615 (9)
C12	0.2255 (6)	0.5127 (2)	0.4565 (3)	0.0842 (12)
H12	0.2398	0.4933	0.5196	0.101*
C13	0.1694 (7)	0.5711 (2)	0.4492 (4)	0.0982 (14)
H13	0.1469	0.5905	0.5076	0.118*
C14	0.1473 (6)	0.59969 (18)	0.3580 (4)	0.0854 (12)
H14	0.1095	0.6387	0.3543	0.102*
C15	0.3392 (6)	0.39343 (19)	0.4619 (3)	0.0919 (13)
H15A	0.4253	0.4130	0.5147	0.138*
H15B	0.3841	0.3550	0.4502	0.138*
H15C	0.2241	0.3900	0.4836	0.138*
C17	0.1111 (6)	0.61685 (18)	−0.0096 (4)	0.0889 (13)
H16A	−0.0209	0.6203	−0.0257	0.107*
H16B	0.1619	0.6560	0.0028	0.107*
C18	0.1737 (7)	0.59090 (18)	−0.0957 (4)	0.0952 (14)
H17A	0.2791	0.6124	−0.1086	0.114*
H17B	0.0782	0.5938	−0.1571	0.114*
C19	0.9741 (5)	0.27798 (17)	0.4624 (3)	0.0681 (9)
C20	0.7695 (6)	0.31745 (18)	0.3323 (3)	0.0762 (9)
C16	0.1480 (5)	0.60153 (15)	0.1717 (3)	0.0691 (10)
H20	0.1091	0.6404	0.1724	0.083*

	U11	U22	U33	U12	U13	U23
Ni1	0.0435 (2)	0.0440 (2)	0.0519 (3)	−0.00269 (17)	0.00649 (17)	0.00924 (18)
Na1	0.0576 (7)	0.0475 (7)	0.0521 (7)	0.0048 (6)	0.0090 (6)	0.0046 (5)
O1	0.0737 (15)	0.0407 (11)	0.0502 (13)	0.0055 (10)	0.0146 (11)	−0.0009 (10)
O2	0.0576 (13)	0.0493 (12)	0.0426 (12)	0.0010 (10)	0.0109 (10)	0.0014 (9)
O3	0.115 (2)	0.0601 (15)	0.0482 (14)	0.0084 (14)	0.0235 (13)	0.0051 (11)
O4	0.0800 (16)	0.0474 (13)	0.0746 (17)	−0.0003 (11)	0.0284 (13)	−0.0082 (12)
O5	0.0885 (17)	0.0713 (15)	0.0650 (16)	−0.0195 (13)	0.0290 (13)	−0.0105 (12)
N1	0.0475 (16)	0.0432 (15)	0.081 (2)	−0.0028 (12)	0.0046 (14)	0.0120 (15)
N2	0.0461 (16)	0.0653 (18)	0.0625 (19)	−0.0061 (13)	0.0036 (14)	0.0215 (15)
N3	0.0765 (19)	0.131 (2)	0.0687 (18)	0.0310 (17)	0.0164 (15)	0.0124 (18)
N4	0.099 (2)	0.085 (2)	0.076 (2)	0.0171 (19)	0.0042 (18)	0.0172 (18)
N5	0.0782 (19)	0.125 (2)	0.0725 (19)	0.0268 (18)	0.0037 (16)	0.0108 (17)
C1	0.046 (2)	0.100 (3)	0.049 (2)	−0.0013 (19)	0.0089 (15)	−0.001 (2)
C2	0.0405 (17)	0.070 (2)	0.0432 (19)	−0.0088 (16)	0.0099 (14)	−0.0071 (16)
C3	0.056 (2)	0.067 (2)	0.060 (2)	−0.0097 (17)	0.0196 (17)	−0.0206 (19)
C4	0.088 (3)	0.097 (3)	0.083 (3)	−0.003 (2)	0.023 (2)	−0.034 (3)
C5	0.119 (4)	0.159 (5)	0.066 (3)	0.015 (4)	0.027 (3)	−0.038 (3)
C6	0.097 (3)	0.160 (5)	0.044 (2)	0.008 (3)	0.018 (2)	−0.009 (3)
C7	0.051 (2)	0.108 (3)	0.048 (2)	−0.007 (2)	0.0077 (16)	0.021 (2)
C8	0.111 (3)	0.045 (2)	0.124 (4)	0.000 (2)	0.045 (3)	−0.009 (2)
C9	0.057 (2)	0.052 (2)	0.079 (3)	0.0015 (16)	0.0093 (18)	−0.0180 (19)
C10	0.0513 (19)	0.0493 (18)	0.057 (2)	−0.0025 (15)	0.0122 (15)	−0.0081 (16)
C11	0.066 (2)	0.065 (2)	0.056 (2)	−0.0009 (18)	0.0165 (17)	−0.0114 (18)
C12	0.097 (3)	0.100 (3)	0.057 (3)	0.000 (3)	0.019 (2)	−0.018 (2)
C13	0.111 (4)	0.099 (4)	0.088 (4)	0.006 (3)	0.027 (3)	−0.043 (3)
C14	0.083 (3)	0.071 (3)	0.102 (3)	0.015 (2)	0.016 (2)	−0.033 (3)
C15	0.124 (4)	0.096 (3)	0.058 (2)	0.001 (3)	0.025 (2)	0.022 (2)
C17	0.079 (3)	0.075 (3)	0.113 (4)	0.017 (2)	0.018 (3)	0.047 (3)
C18	0.108 (3)	0.080 (3)	0.094 (3)	0.005 (3)	0.011 (3)	0.041 (3)
C19	0.0625 (19)	0.080 (2)	0.0614 (18)	0.0125 (16)	0.0121 (16)	0.0107 (18)
C20	0.068 (2)	0.105 (2)	0.0550 (18)	0.0168 (19)	0.0113 (16)	0.0098 (18)
C16	0.061 (2)	0.0391 (18)	0.102 (3)	0.0030 (16)	0.004 (2)	−0.006 (2)

Ni1—O1	1.838 (2)	C3—C4	1.371 (5)
Ni1—N2	1.839 (3)	C4—C5	1.387 (6)
Ni1—N1	1.840 (3)	C4—H4	0.9300
Ni1—O2	1.8457 (19)	C5—C6	1.361 (7)
Na1—O5	2.288 (2)	C5—H5	0.9300
Na1—O1	2.362 (2)	C6—H6	0.9300
Na1—N5	2.368 (4)	C7—H7	0.9300
Na1—O2	2.395 (2)	C8—H8A	0.9600
Na1—O3	2.492 (3)	C8—H8B	0.9600
Na1—O4	2.555 (2)	C8—H8C	0.9600
O1—C10	1.314 (4)	C9—C10	1.412 (4)
O2—C2	1.310 (3)	C9—C16	1.413 (5)
O3—C11	1.365 (4)	C9—C14	1.419 (5)
O3—C15	1.420 (4)	C10—C11	1.410 (5)
O4—C3	1.365 (4)	C11—C12	1.375 (5)
O4—C8	1.429 (4)	C12—C13	1.389 (6)
O5—H5A	0.8200	C12—H12	0.9300
O5—H5B	0.8246	C13—C14	1.349 (6)
N1—C16	1.276 (4)	C13—H13	0.9300
N1—C17	1.476 (4)	C14—H14	0.9300
N2—C7	1.282 (4)	C15—H15A	0.9600
N2—C18	1.468 (5)	C15—H15B	0.9600
N3—C19	1.292 (5)	C15—H15C	0.9600
N3—C20	1.297 (5)	C17—C18	1.436 (6)
N4—C19	1.127 (4)	C17—H16A	0.9700
N5—C20	1.127 (4)	C17—H16B	0.9700
C1—C6	1.405 (5)	C18—H17A	0.9700
C1—C2	1.411 (5)	C18—H17B	0.9700
C1—C7	1.425 (5)	C16—H20	0.9300
C2—C3	1.419 (5)
O1—Ni1—N2	178.09 (11)	C6—C5—C4	120.6 (4)
O1—Ni1—N1	94.79 (11)	C6—C5—H5	119.7
N2—Ni1—N1	86.76 (14)	C4—C5—H5	119.7
O1—Ni1—O2	83.62 (9)	C5—C6—C1	120.5 (4)
N2—Ni1—O2	94.82 (11)	C5—C6—H6	119.7
N1—Ni1—O2	178.41 (11)	C1—C6—H6	119.7
O5—Na1—O1	120.42 (9)	N2—C7—C1	125.7 (3)
O5—Na1—N5	101.85 (12)	N2—C7—H7	117.1
O1—Na1—N5	127.99 (12)	C1—C7—H7	117.1
O5—Na1—O2	116.86 (9)	O4—C8—H8A	109.5
O1—Na1—O2	62.15 (7)	O4—C8—H8B	109.5
N5—Na1—O2	124.88 (11)	H8A—C8—H8B	109.5
O5—Na1—O3	90.51 (9)	O4—C8—H8C	109.5
O1—Na1—O3	64.15 (8)	H8A—C8—H8C	109.5
N5—Na1—O3	88.43 (11)	H8B—C8—H8C	109.5
O2—Na1—O3	126.30 (8)	C10—C9—C16	121.1 (3)
O5—Na1—O4	84.15 (8)	C10—C9—C14	118.6 (4)
O1—Na1—O4	124.77 (9)	C16—C9—C14	120.2 (4)
N5—Na1—O4	85.68 (11)	O1—C10—C11	118.0 (3)
O2—Na1—O4	62.63 (7)	O1—C10—C9	123.4 (3)
O3—Na1—O4	171.07 (9)	C11—C10—C9	118.6 (3)
C10—O1—Ni1	127.8 (2)	O3—C11—C12	125.5 (4)
C10—O1—Na1	124.3 (2)	O3—C11—C10	113.8 (3)
Ni1—O1—Na1	107.87 (9)	C12—C11—C10	120.7 (4)
C2—O2—Ni1	127.3 (2)	C11—C12—C13	120.4 (4)
C2—O2—Na1	125.61 (19)	C11—C12—H12	119.8
Ni1—O2—Na1	106.26 (9)	C13—C12—H12	119.8
C11—O3—C15	118.3 (3)	C14—C13—C12	120.3 (4)
C11—O3—Na1	119.68 (19)	C14—C13—H13	119.8
C15—O3—Na1	122.0 (2)	C12—C13—H13	119.8
C3—O4—C8	118.2 (3)	C13—C14—C9	121.3 (4)
C3—O4—Na1	119.73 (19)	C13—C14—H14	119.3
C8—O4—Na1	122.1 (2)	C9—C14—H14	119.3
Na1—O5—H5A	130.6	O3—C15—H15A	109.5
Na1—O5—H5B	118.8	O3—C15—H15B	109.5
H5A—O5—H5B	110.0	H15A—C15—H15B	109.5
C16—N1—C17	119.2 (3)	O3—C15—H15C	109.5
C16—N1—Ni1	126.4 (2)	H15A—C15—H15C	109.5
C17—N1—Ni1	114.3 (3)	H15B—C15—H15C	109.5
C7—N2—C18	118.9 (3)	C18—C17—N1	110.7 (3)
C7—N2—Ni1	126.8 (3)	C18—C17—H16A	109.5
C18—N2—Ni1	114.2 (3)	N1—C17—H16A	109.5
C19—N3—C20	120.5 (3)	C18—C17—H16B	109.5
C20—N5—Na1	171.8 (4)	N1—C17—H16B	109.5
C6—C1—C2	119.6 (4)	H16A—C17—H16B	108.1
C6—C1—C7	119.2 (4)	C17—C18—N2	111.4 (3)
C2—C1—C7	121.1 (3)	C17—C18—H17A	109.4
O2—C2—C1	123.9 (3)	N2—C18—H17A	109.4
O2—C2—C3	117.9 (3)	C17—C18—H17B	109.4
C1—C2—C3	118.2 (3)	N2—C18—H17B	109.4
O4—C3—C4	126.1 (4)	H17A—C18—H17B	108.0
O4—C3—C2	113.4 (3)	N4—C19—N3	173.6 (4)
C4—C3—C2	120.4 (4)	N5—C20—N3	173.8 (4)
C3—C4—C5	120.5 (4)	N1—C16—C9	126.5 (3)
C3—C4—H4	119.7	N1—C16—H20	116.7
C5—C4—H4	119.7	C9—C16—H20	116.7

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N3i	0.82	2.14	2.960 (4)	175
O5—H5B···N4ii	0.82	2.03	2.852 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N3i	0.82	2.14	2.960 (4)	175
O5—H5B⋯N4ii	0.82	2.03	2.852 (4)	177

Symmetry codes: (i) ; (ii) .