{μ-6,6′-Dimeth­oxy-2,2′-[ethane-1,2-diyl­bis(nitrilo­methyl­idyne)]diphenolato-1κ4O6,O1,O1′,O6′:2κ4O1,N,N′,O1′}(methanol-1κO)(perchlorato-1κO)nickel(II)sodium

Xiao, H.-Q.

doi:10.1107/S1600536809007776

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m400

doi:10.1107/S1600536809007776

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{μ-6,6′-Dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O⁶,O¹,O^1′,O^6′:2κ⁴O¹,N,N′,O^1′}(methanol-1κO)(perchlorato-1κO)nickel(II)sodium

Hui-Quan Xiao ^a ^*

^aDepartment of Chemistry, Shaoxing University, Shaoxing 312000, People's Republic of China
^*Correspondence e-mail: chemreagent@yahoo.cn

(Received 18 February 2009; accepted 3 March 2009; online 14 March 2009)

The molecule of the title compound, [NaNi(C₁₈H₁₈N₂O₄)(ClO₄)(CH₃OH)], is almost planar, the maximum deviation from the molecular plane being 5.3 (1) Å. The Ni²⁺ ion is N₂O₂ 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)(ClO₄)(CH₄O)]
M_r = 539.54
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.159
S = 1.06
3906 reflections
339 parameters
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007776/hg2479sup1.cif

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

checkCIF report

Comment top

Schiff bases have been known as effective ligands for metal ions and used in the mechanism of many biochemical processes (Lindoy et al., 1976). N,N-disalicylideneethylenediamine type Schiff bases ligands present versatile steric, electronic and lipophilic properties (Correia et al., 2005). We report here the synthesis and crystal structure of the title compound (I). The molecular structure of (I) is shown in Fig.1. The values of the geometric parameters in (I) are normal (Allen et al., 1987). Ni(II) and Na(I) are connected via two bridging oxygen atoms of the ligand. The six-coordinate Na atom adopts a distorted octahedral coordination geometry is completed by the O atoms derived from a perchlorate anion, while the four-coordinate Ni gives plane coordination.

Related literature top

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 top

A mixture of 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol (1 mmol) and nickel chloride (1 mmol) in absolute ethanol (15 ml) was stirred for 30 min and sodium perchlorate (1 mmol) was added, stirred for another 15 min and then filtered. The resulting clear orange solution was evaporated at room temperature for 7 days, after which large orange block-shaped crystals of the title complex suitable for X-ray diffraction analysis were obtained.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The independent molecules of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

{µ-6,6'-Dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O⁶,O¹,O^1',O^6': 2κ⁴O¹,N,N',O^1'}(methanol- 1κO)(perchlorato-1κO)nickel(II)sodium top

Crystal data top

[NaNi(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]	F(000) = 1111.9
M_r = 539.54	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0852P)² + 3.4175P] where P = (F_o² + 2F_c²)/3
3906 reflections	(Δ/σ)_max = 0.001
339 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −1.14 e Å⁻³

Crystal data top

[NaNi(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]	V = 2218.0 (8) Å³
M_r = 539.54	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.026 (2) Å	µ = 1.07 mm⁻¹
b = 8.1360 (16) Å	T = 273 K
c = 23.394 (5) Å	0.14 × 0.12 × 0.11 mm
β = 104.302 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3906 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3120 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.892	R_int = 0.023
10559 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.06	Δρ_max = 1.03 e Å⁻³
3906 reflections	Δρ_min = −1.14 e Å⁻³
339 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[NaNi(C₁₈H₁₈N₂O₄)(ClO₄)(CH₄O)]
M_r	539.54
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	12.026 (2), 8.1360 (16), 23.394 (5)
β (°)	104.302 (3)
V (Å³)	2218.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.07
Crystal size (mm)	0.14 × 0.12 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.865, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	10559, 3906, 3120
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.159, 1.06
No. of reflections	3906
No. of parameters	339
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −1.14

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work is supported by the Zhejiang Provincial Natural Science Foundation (Y4080481).

References

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