Bis(6-meth­oxy-2-{[tris­(hydroxy­meth­yl)methyl-κO]imino­meth­yl}phenolato-κ2N,O1)nickel(II) dihydrate

Zhou, T.; Zhou, R.-J.; An, Z.

doi:10.1107/S1600536809022028

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m779

doi:10.1107/S1600536809022028

Open

access

Bis(6-methoxy-2-{[tris(hydroxymethyl)methyl-κO]iminomethyl}phenolato-κ²N,O¹)nickel(II) dihydrate

Tian Zhou,^a ^* Ru-Jin Zhou ^a and Zhe An ^a

^aSchool of Chemistry and Life Science, Maoming University, Maoming 525000, People's Republic of China
^*Correspondence e-mail: zhoutian016@163.com

(Received 19 May 2009; accepted 10 June 2009; online 17 June 2009)

In the title compound, [Ni(C₁₂H₁₆NO₅)₂]·2H₂O, the Ni^II atom is coordinated by four O atoms and two N atoms from the two 6-methoxy-2-{[tris(hydroxymethyl)methyl]iminomethyl}phenolate ligands in a distorted octahedral coordination geometry. O—H⋯O hydrogen bonds link the complexes and uncoordinated water molecules into two-dimensional networks parallel to (001).

Related literature

For the applications of Schiff-base complexes, see: Kritagawa & Kondo (1998 ); Zhang et al. (1998 ); Yaghi et al. (1996 ).

Experimental

Crystal data

[Ni(C₁₂H₁₆NO₅)₂]·2H₂O
M_r = 603.26
Monoclinic, P 2₁ /c
a = 12.0142 (10) Å
b = 10.9876 (10) Å
c = 20.324 (2) Å
β = 97.501 (1)°
V = 2660.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 293 K
0.44 × 0.29 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.721, T_max = 0.857
13321 measured reflections
4933 independent reflections
4436 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.00
4933 reflections
376 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.85	2.670 (3)	179
O2—H2A⋯O11ⁱⁱ	0.82	1.91	2.666 (3)	152
O2—H2A⋯O12ⁱⁱ	0.82	2.37	3.010 (3)	135
O5—H5⋯O6ⁱⁱⁱ	0.82	1.87	2.691 (3)	174
O6—H6⋯O3^iv	0.82	1.89	2.671 (2)	159
O10—H10A⋯O5^iv	0.82 (3)	1.93 (3)	2.751 (3)	175 (5)
O8—H1AA⋯O7ⁱ	0.82 (2)	1.972 (11)	2.775 (4)	166 (4)
O4—H4AA⋯O8^v	0.82 (3)	1.88 (4)	2.686 (3)	170 (4)
O8—H1BB⋯O2^vi	0.82 (3)	2.16 (3)	2.962 (3)	167 (4)
O7—H2BB⋯O9ⁱⁱ	0.82 (2)	2.055 (10)	2.862 (4)	168 (4)
O7—H2AA⋯O1	0.81 (3)	1.84 (3)	2.641 (3)	169 (4)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) x, y-1, z; (vi) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022028/bi2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022028/bi2378Isup2.hkl

checkCIF report

Comment top

Polymeric metal complexes containing Schiff-base ligands are of interest because of their useful chemical or physical properties (Zhang et al., 1998; Kritagawa & Kondo, 1998; Yaghi et al., 1996). Herein, we report a new crystal structure containing the Schiff-base ligand 6-methoxy-2-{[tris(hydroxymethyl)methyl]iminomethyl}phenol (denoted HL).

As shown in Figure 1, the asymmetric unit of the complex comprises two L^- ligands, one Ni^II atom and two lattice water molecules. The Ni^II atom is hexa-coordinated by four O atoms and two N atoms from the two L^- ligands, giving a distorted octahedral coordination geometry. The Ni—O and Ni—N bond distances are within normal ranges. The [NiL₂] complexes form an extensive network of O—H···O interactions involving the lattice water molecules, giving 2-D networks parallel to the (001) planes (Fig. 2).

Related literature top

For the applications of Schiff-base complexes, see: Kritagawa & Kondo (1998); Zhang et al. (1998); Yaghi et al. (1996).

Experimental top

The complex was synthesized by refluxing HL (0.050 g, 0.2 mmol) and NiCl₂.6H₂O (0.048 g, 0.2 mmol) in the mixed solution (CH₃OH:H₂O = 4:1) until all solid was dissolved. The solution was then cooled to room temperature and filtered. Green crystals for X-ray diffraction analysis were obtained by slow evaporation of the filtrate. Elemental analysis calculated: C 47.74, H 5.97, N 4.64 %; found: C 47.69, H 5.51, N 4.58 %.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. Molecular structure with displacement ellipsoids drawn at the 30% probability level for non-H atoms.
	Fig. 2. Packing diagram viewed approximately along the c axis, showing the complex network of O—H···O hydrogen bonds (dashed lines).

Bis(6-methoxy-2-{[tris(hydroxymethyl)methyl- κO]iminomethyl}phenolato-κ²N,O¹)nickel(II) dihydrate top

Crystal data top

[Ni(C₁₂H₁₆NO₅)₂]·2H₂O	F(000) = 1272
M_r = 603.26	D_x = 1.506 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4933 reflections
a = 12.0142 (10) Å	θ = 2.0–25.5°
b = 10.9876 (10) Å	µ = 0.80 mm⁻¹
c = 20.324 (2) Å	T = 293 K
β = 97.501 (1)°	Block, green
V = 2660.0 (4) Å³	0.44 × 0.29 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4933 independent reflections
Radiation source: fine-focus sealed tube	4436 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→11
T_min = 0.721, T_max = 0.857	k = −13→13
13321 measured reflections	l = −24→21

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.069P)² + 2.387P] where P = (F_o² + 2F_c²)/3
4933 reflections	(Δ/σ)_max = 0.032
376 parameters	Δρ_max = 0.38 e Å⁻³
8 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Ni(C₁₂H₁₆NO₅)₂]·2H₂O	V = 2660.0 (4) Å³
M_r = 603.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0142 (10) Å	µ = 0.80 mm⁻¹
b = 10.9876 (10) Å	T = 293 K
c = 20.324 (2) Å	0.44 × 0.29 × 0.20 mm
β = 97.501 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4933 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	4436 reflections with I > 2σ(I)
T_min = 0.721, T_max = 0.857	R_int = 0.043
13321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	8 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.38 e Å⁻³
4933 reflections	Δρ_min = −0.44 e Å⁻³
376 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
C1	0.9480 (2)	0.2452 (2)	0.86933 (11)	0.0233 (5)
C2	1.0283 (2)	0.2677 (3)	0.92480 (12)	0.0311 (6)
H2	1.1023	0.2433	0.9242	0.037*
C3	0.9989 (3)	0.3243 (3)	0.97874 (13)	0.0386 (7)
H3	1.0524	0.3390	1.0153	0.046*
C4	0.8871 (3)	0.3610 (3)	0.97952 (14)	0.0391 (7)
H4	0.8671	0.4003	1.0168	0.047*
C5	0.8073 (2)	0.3402 (2)	0.92655 (13)	0.0307 (6)
C6	0.8335 (2)	0.2797 (2)	0.86879 (11)	0.0228 (5)
C7	0.6684 (2)	0.3019 (2)	0.62935 (12)	0.0231 (5)
C8	0.6897 (3)	0.3685 (2)	0.57276 (13)	0.0325 (6)
C9	0.6097 (3)	0.3783 (3)	0.51866 (15)	0.0468 (8)
H9	0.6251	0.4238	0.4823	0.056*
C10	0.5051 (3)	0.3210 (3)	0.51678 (16)	0.0515 (9)
H10	0.4509	0.3307	0.4801	0.062*
C11	0.4834 (3)	0.2522 (3)	0.56833 (15)	0.0404 (7)
H11	0.4143	0.2136	0.5668	0.048*
C12	0.5639 (2)	0.2379 (2)	0.62428 (12)	0.0269 (5)
C13	0.8357 (4)	0.4634 (4)	0.52069 (18)	0.0638 (11)
H13A	0.8300	0.3993	0.4883	0.096*
H13B	0.9128	0.4872	0.5312	0.096*
H13C	0.7921	0.5319	0.5030	0.096*
C14	0.5356 (2)	0.1521 (2)	0.67266 (13)	0.0265 (5)
H14	0.4621	0.1238	0.6679	0.032*
C15	0.5631 (2)	0.0166 (2)	0.76457 (13)	0.0264 (5)
C16	0.6607 (2)	−0.0731 (2)	0.77949 (14)	0.0312 (6)
H16A	0.6454	−0.1291	0.8141	0.037*
H16B	0.6694	−0.1199	0.7400	0.037*
C17	0.4562 (2)	−0.0513 (3)	0.73736 (15)	0.0344 (6)
H17A	0.4381	−0.1104	0.7698	0.041*
H17B	0.3943	0.0059	0.7296	0.041*
C18	0.5411 (3)	0.0770 (3)	0.82811 (14)	0.0370 (6)
H18A	0.5226	0.0156	0.8592	0.044*
H18B	0.6083	0.1190	0.8478	0.044*
C19	0.6632 (3)	0.4399 (3)	0.97696 (15)	0.0488 (8)
H19A	0.6755	0.3908	1.0163	0.073*
H19B	0.5850	0.4603	0.9678	0.073*
H19C	0.7068	0.5131	0.9835	0.073*
C20	0.9938 (2)	0.1930 (2)	0.81394 (12)	0.0228 (5)
H20	1.0712	0.1823	0.8182	0.027*
C21	0.9989 (2)	0.1161 (2)	0.70684 (12)	0.0229 (5)
C22	0.9245 (2)	0.0216 (2)	0.66780 (12)	0.0260 (5)
H22A	0.9502	0.0080	0.6251	0.031*
H22B	0.9290	−0.0549	0.6918	0.031*
C23	1.0163 (2)	0.2240 (2)	0.66147 (12)	0.0276 (5)
H23A	1.0622	0.1977	0.6282	0.033*
H23B	0.9441	0.2490	0.6386	0.033*
C24	1.1143 (2)	0.0572 (2)	0.72948 (13)	0.0282 (5)
H24A	1.1428	0.0193	0.6919	0.034*
H24B	1.1675	0.1189	0.7475	0.034*
N1	0.93758 (17)	0.16035 (17)	0.75960 (9)	0.0199 (4)
N2	0.60221 (17)	0.11097 (18)	0.72161 (10)	0.0228 (4)
Ni1	0.76754 (2)	0.15968 (3)	0.742167 (14)	0.01963 (12)
O1	0.4508 (2)	0.1618 (2)	0.81592 (14)	0.0531 (6)
H1	0.4759	0.2313	0.8178	0.080*
O2	0.46970 (17)	−0.11101 (19)	0.67775 (11)	0.0418 (5)
H2A	0.4079	−0.1255	0.6571	0.063*
O3	0.74281 (14)	0.30277 (15)	0.68125 (8)	0.0233 (4)
O4	0.81045 (15)	0.06375 (17)	0.65815 (9)	0.0301 (4)
O5	1.06823 (16)	0.32512 (17)	0.69579 (10)	0.0341 (4)
H5	1.0200	0.3734	0.7042	0.051*
O6	1.10157 (16)	−0.03050 (19)	0.77806 (11)	0.0399 (5)
H6	1.1596	−0.0702	0.7859	0.060*
O7	0.2701 (2)	0.1557 (2)	0.87725 (16)	0.0584 (7)
O8	0.6646 (2)	0.8964 (2)	0.60240 (12)	0.0524 (6)
O9	0.79479 (19)	0.4219 (2)	0.57859 (10)	0.0440 (5)
O10	0.76155 (15)	−0.00657 (17)	0.80057 (10)	0.0311 (4)
O11	0.69602 (18)	0.3743 (2)	0.92284 (10)	0.0446 (5)
O12	0.75320 (14)	0.26451 (16)	0.82089 (8)	0.0258 (4)
H10A	0.815 (2)	−0.054 (3)	0.803 (2)	0.080*
H1AA	0.690 (3)	0.8269 (14)	0.603 (2)	0.080*
H2AA	0.329 (2)	0.151 (3)	0.862 (2)	0.080*
H4AA	0.768 (3)	0.008 (3)	0.645 (2)	0.080*
H1BB	0.605 (2)	0.902 (3)	0.618 (2)	0.080*
H2BB	0.243 (3)	0.0900 (16)	0.886 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0281 (12)	0.0218 (12)	0.0198 (11)	−0.0011 (10)	0.0026 (9)	−0.0003 (9)
C2	0.0308 (13)	0.0363 (15)	0.0247 (13)	0.0002 (12)	−0.0020 (10)	0.0005 (11)
C3	0.0432 (17)	0.0480 (18)	0.0220 (13)	−0.0017 (14)	−0.0059 (12)	−0.0053 (12)
C4	0.0487 (18)	0.0460 (17)	0.0222 (13)	0.0024 (14)	0.0036 (12)	−0.0104 (12)
C5	0.0367 (15)	0.0310 (14)	0.0247 (13)	0.0056 (11)	0.0052 (11)	−0.0026 (10)
C6	0.0300 (13)	0.0203 (11)	0.0177 (11)	−0.0016 (10)	0.0022 (9)	0.0016 (9)
C7	0.0293 (13)	0.0164 (11)	0.0232 (12)	0.0003 (10)	0.0022 (10)	−0.0012 (9)
C8	0.0461 (16)	0.0242 (13)	0.0265 (13)	−0.0038 (12)	0.0026 (11)	0.0015 (10)
C9	0.073 (2)	0.0381 (16)	0.0257 (14)	−0.0042 (16)	−0.0061 (14)	0.0096 (12)
C10	0.065 (2)	0.0432 (18)	0.0374 (17)	−0.0052 (16)	−0.0254 (16)	0.0094 (14)
C11	0.0407 (16)	0.0311 (15)	0.0442 (17)	−0.0031 (12)	−0.0144 (13)	0.0020 (12)
C12	0.0294 (13)	0.0217 (12)	0.0276 (12)	0.0018 (10)	−0.0035 (10)	−0.0005 (10)
C13	0.094 (3)	0.053 (2)	0.052 (2)	−0.018 (2)	0.040 (2)	−0.0003 (17)
C14	0.0231 (12)	0.0206 (12)	0.0346 (14)	−0.0017 (10)	−0.0015 (10)	−0.0026 (10)
C15	0.0262 (12)	0.0206 (12)	0.0333 (13)	−0.0046 (10)	0.0068 (10)	0.0036 (10)
C16	0.0318 (14)	0.0220 (13)	0.0391 (14)	−0.0031 (11)	0.0022 (11)	0.0055 (11)
C17	0.0268 (13)	0.0267 (14)	0.0494 (17)	−0.0059 (11)	0.0037 (12)	0.0054 (12)
C18	0.0429 (16)	0.0336 (15)	0.0375 (15)	−0.0038 (13)	0.0170 (12)	0.0044 (12)
C19	0.056 (2)	0.057 (2)	0.0362 (16)	0.0188 (16)	0.0167 (14)	−0.0120 (15)
C20	0.0223 (12)	0.0202 (11)	0.0253 (12)	−0.0011 (10)	0.0011 (9)	0.0006 (9)
C21	0.0248 (12)	0.0220 (12)	0.0225 (11)	0.0003 (10)	0.0056 (9)	−0.0032 (9)
C22	0.0307 (13)	0.0203 (12)	0.0265 (12)	0.0007 (10)	0.0022 (10)	−0.0055 (10)
C23	0.0331 (13)	0.0269 (13)	0.0239 (12)	−0.0017 (11)	0.0080 (10)	−0.0004 (10)
C24	0.0267 (13)	0.0261 (13)	0.0322 (13)	0.0031 (10)	0.0054 (10)	−0.0007 (10)
N1	0.0236 (10)	0.0174 (10)	0.0190 (10)	0.0009 (8)	0.0044 (8)	0.0006 (7)
N2	0.0221 (10)	0.0186 (10)	0.0276 (11)	−0.0009 (8)	0.0028 (8)	−0.0005 (8)
Ni1	0.02003 (18)	0.01864 (18)	0.01981 (18)	−0.00071 (11)	0.00109 (12)	−0.00067 (11)
O1	0.0484 (14)	0.0359 (12)	0.0817 (18)	0.0007 (10)	0.0338 (13)	−0.0071 (12)
O2	0.0364 (11)	0.0328 (11)	0.0528 (13)	−0.0080 (9)	−0.0074 (9)	−0.0070 (10)
O3	0.0269 (9)	0.0198 (8)	0.0223 (8)	−0.0042 (7)	−0.0004 (7)	0.0010 (7)
O4	0.0286 (9)	0.0285 (10)	0.0319 (10)	−0.0018 (8)	−0.0014 (7)	−0.0101 (8)
O5	0.0351 (11)	0.0263 (10)	0.0421 (11)	−0.0068 (8)	0.0096 (9)	−0.0016 (8)
O6	0.0309 (10)	0.0326 (11)	0.0560 (13)	0.0111 (9)	0.0046 (9)	0.0139 (9)
O7	0.0449 (14)	0.0510 (15)	0.0836 (19)	0.0014 (11)	0.0248 (13)	−0.0003 (13)
O8	0.0615 (16)	0.0469 (14)	0.0485 (13)	−0.0191 (12)	0.0057 (11)	−0.0043 (11)
O9	0.0523 (13)	0.0463 (12)	0.0351 (11)	−0.0156 (10)	0.0125 (9)	0.0085 (9)
O10	0.0281 (9)	0.0250 (9)	0.0390 (10)	0.0007 (8)	−0.0004 (8)	0.0041 (8)
O11	0.0417 (12)	0.0646 (14)	0.0275 (10)	0.0182 (11)	0.0046 (9)	−0.0162 (10)
O12	0.0246 (9)	0.0298 (9)	0.0222 (8)	0.0023 (7)	0.0008 (7)	−0.0059 (7)

Geometric parameters (Å, º) top

C1—C2	1.406 (3)	C17—H17B	0.970
C1—C6	1.426 (4)	C18—O1	1.427 (4)
C1—C20	1.435 (3)	C18—H18A	0.970
C2—C3	1.347 (4)	C18—H18B	0.970
C2—H2	0.930	C19—O11	1.414 (3)
C3—C4	1.405 (5)	C19—H19A	0.960
C3—H3	0.930	C19—H19B	0.960
C4—C5	1.364 (4)	C19—H19C	0.960
C4—H4	0.930	C20—N1	1.269 (3)
C5—O11	1.381 (3)	C20—H20	0.930
C5—C6	1.419 (3)	C21—N1	1.461 (3)
C6—O12	1.289 (3)	C21—C22	1.524 (3)
C7—O3	1.290 (3)	C21—C23	1.533 (3)
C7—C8	1.414 (4)	C21—C24	1.545 (3)
C7—C12	1.431 (4)	C22—O4	1.435 (3)
C8—C9	1.366 (4)	C22—H22A	0.970
C8—O9	1.384 (4)	C22—H22B	0.970
C9—C10	1.402 (5)	C23—O5	1.413 (3)
C9—H9	0.930	C23—H23A	0.970
C10—C11	1.345 (5)	C23—H23B	0.970
C10—H10	0.930	C24—O6	1.402 (3)
C11—C12	1.402 (4)	C24—H24A	0.970
C11—H11	0.930	C24—H24B	0.970
C12—C14	1.435 (4)	N1—Ni1	2.027 (2)
C13—O9	1.409 (4)	N2—Ni1	2.047 (2)
C13—H13A	0.960	Ni1—O12	1.9971 (17)
C13—H13B	0.960	Ni1—O3	1.9993 (17)
C13—H13C	0.960	Ni1—O4	2.1266 (18)
C14—N2	1.275 (3)	Ni1—O10	2.1847 (19)
C14—H14	0.930	O1—H1	0.820
C15—N2	1.471 (3)	O2—H2A	0.820
C15—C18	1.506 (4)	O4—H4AA	0.82 (3)
C15—C17	1.526 (3)	O5—H5	0.820
C15—C16	1.531 (4)	O6—H6	0.820
C16—O10	1.432 (3)	O7—H2AA	0.81 (3)
C16—H16A	0.970	O7—H2BB	0.82 (2)
C16—H16B	0.970	O8—H1AA	0.82 (2)
C17—O2	1.406 (4)	O8—H1BB	0.82 (3)
C17—H17A	0.970	O10—H10A	0.82 (3)

C2—C1—C6	121.3 (2)	O11—C19—H19B	109.5
C2—C1—C20	114.0 (2)	H19A—C19—H19B	109.5
C6—C1—C20	124.6 (2)	O11—C19—H19C	109.5
C3—C2—C1	120.6 (3)	H19A—C19—H19C	109.5
C3—C2—H2	119.7	H19B—C19—H19C	109.5
C1—C2—H2	119.7	N1—C20—C1	125.5 (2)
C2—C3—C4	119.6 (3)	N1—C20—H20	117.2
C2—C3—H3	120.2	C1—C20—H20	117.2
C4—C3—H3	120.2	N1—C21—C22	106.9 (2)
C5—C4—C3	121.2 (3)	N1—C21—C23	107.81 (19)
C5—C4—H4	119.4	C22—C21—C23	109.3 (2)
C3—C4—H4	119.4	N1—C21—C24	116.1 (2)
C4—C5—O11	125.0 (2)	C22—C21—C24	108.2 (2)
C4—C5—C6	121.5 (3)	C23—C21—C24	108.4 (2)
O11—C5—C6	113.5 (2)	O4—C22—C21	109.65 (19)
O12—C6—C5	117.4 (2)	O4—C22—H22A	109.7
O12—C6—C1	126.7 (2)	C21—C22—H22A	109.7
C5—C6—C1	115.9 (2)	O4—C22—H22B	109.7
O3—C7—C8	118.8 (2)	C21—C22—H22B	109.7
O3—C7—C12	124.8 (2)	H22A—C22—H22B	108.2
C8—C7—C12	116.4 (2)	O5—C23—C21	113.4 (2)
C9—C8—O9	125.0 (3)	O5—C23—H23A	108.9
C9—C8—C7	120.8 (3)	C21—C23—H23A	108.9
O9—C8—C7	114.2 (2)	O5—C23—H23B	108.9
C8—C9—C10	121.3 (3)	C21—C23—H23B	108.9
C8—C9—H9	119.3	H23A—C23—H23B	107.7
C10—C9—H9	119.3	O6—C24—C21	108.7 (2)
C11—C10—C9	119.7 (3)	O6—C24—H24A	109.9
C11—C10—H10	120.2	C21—C24—H24A	109.9
C9—C10—H10	120.2	O6—C24—H24B	109.9
C10—C11—C12	120.8 (3)	C21—C24—H24B	109.9
C10—C11—H11	119.6	H24A—C24—H24B	108.3
C12—C11—H11	119.6	C20—N1—C21	118.1 (2)
C11—C12—C7	120.6 (2)	C20—N1—Ni1	124.24 (17)
C11—C12—C14	115.5 (2)	C21—N1—Ni1	117.62 (15)
C7—C12—C14	123.9 (2)	C14—N2—C15	119.8 (2)
O9—C13—H13A	109.5	C14—N2—Ni1	124.04 (18)
O9—C13—H13B	109.5	C15—N2—Ni1	116.08 (15)
H13A—C13—H13B	109.5	O12—Ni1—O3	91.21 (7)
O9—C13—H13C	109.5	O12—Ni1—N1	92.77 (7)
H13A—C13—H13C	109.5	O3—Ni1—N1	99.80 (7)
H13B—C13—H13C	109.5	O12—Ni1—N2	97.55 (8)
N2—C14—C12	126.0 (2)	O3—Ni1—N2	91.00 (7)
N2—C14—H14	117.0	N1—Ni1—N2	164.91 (8)
C12—C14—H14	117.0	O12—Ni1—O4	169.89 (7)
N2—C15—C18	107.7 (2)	O3—Ni1—O4	85.67 (7)
N2—C15—C17	116.6 (2)	N1—Ni1—O4	78.33 (7)
C18—C15—C17	107.0 (2)	N2—Ni1—O4	92.12 (8)
N2—C15—C16	106.0 (2)	O12—Ni1—O10	91.98 (7)
C18—C15—C16	109.2 (2)	O3—Ni1—O10	168.87 (7)
C17—C15—C16	110.1 (2)	N1—Ni1—O10	90.69 (7)
O10—C16—C15	109.1 (2)	N2—Ni1—O10	78.01 (7)
O10—C16—H16A	109.9	O4—Ni1—O10	92.89 (7)
C15—C16—H16A	109.9	C18—O1—H1	109.5
O10—C16—H16B	109.9	C17—O2—H2A	109.5
C15—C16—H16B	109.9	C7—O3—Ni1	122.09 (15)
H16A—C16—H16B	108.3	C22—O4—Ni1	112.16 (13)
O2—C17—C15	110.7 (2)	C22—O4—H4AA	110 (3)
O2—C17—H17A	109.5	Ni1—O4—H4AA	115 (3)
C15—C17—H17A	109.5	C23—O5—H5	109.5
O2—C17—H17B	109.5	C24—O6—H6	109.5
C15—C17—H17B	109.5	H2AA—O7—H2BB	115 (3)
H17A—C17—H17B	108.1	H1AA—O8—H1BB	114 (3)
O1—C18—C15	110.7 (2)	C8—O9—C13	118.7 (3)
O1—C18—H18A	109.5	C16—O10—Ni1	110.53 (14)
C15—C18—H18A	109.5	C16—O10—H10A	109 (3)
O1—C18—H18B	109.5	Ni1—O10—H10A	118 (3)
C15—C18—H18B	109.5	C5—O11—C19	117.5 (2)
H18A—C18—H18B	108.1	C6—O12—Ni1	123.07 (16)
O11—C19—H19A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.85	2.670 (3)	179
O2—H2A···O11ⁱⁱ	0.82	1.91	2.666 (3)	152
O2—H2A···O12ⁱⁱ	0.82	2.37	3.010 (3)	135
O5—H5···O6ⁱⁱⁱ	0.82	1.87	2.691 (3)	174
O6—H6···O3^iv	0.82	1.89	2.671 (2)	159
O10—H10A···O5^iv	0.82 (3)	1.93 (3)	2.751 (3)	175 (5)
O8—H1AA···O7ⁱ	0.82 (2)	1.97 (1)	2.775 (4)	166 (4)
O4—H4AA···O8^v	0.82 (3)	1.88 (4)	2.686 (3)	170 (4)
O8—H1BB···O2^vi	0.82 (3)	2.16 (3)	2.962 (3)	167 (4)
O7—H2BB···O9ⁱⁱ	0.82 (2)	2.06 (1)	2.862 (4)	168 (4)
O7—H2AA···O1	0.81 (3)	1.84 (3)	2.641 (3)	169 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, y+1/2, −z+3/2; (iv) −x+2, y−1/2, −z+3/2; (v) x, y−1, z; (vi) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₁₆NO₅)₂]·2H₂O
M_r	603.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.0142 (10), 10.9876 (10), 20.324 (2)
β (°)	97.501 (1)
V (Å³)	2660.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.44 × 0.29 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.721, 0.857
No. of measured, independent and observed [I > 2σ(I)] reflections	13321, 4933, 4436
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.00
No. of reflections	4933
No. of parameters	376
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.44

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.85	2.670 (3)	179.1
O2—H2A···O11ⁱⁱ	0.82	1.91	2.666 (3)	151.8
O2—H2A···O12ⁱⁱ	0.82	2.37	3.010 (3)	135.2
O5—H5···O6ⁱⁱⁱ	0.82	1.87	2.691 (3)	173.7
O6—H6···O3^iv	0.82	1.89	2.671 (2)	159.2
O10—H10A···O5^iv	0.82 (3)	1.93 (3)	2.751 (3)	175 (5)
O8—H1AA···O7ⁱ	0.82 (2)	1.972 (11)	2.775 (4)	166 (4)
O4—H4AA···O8^v	0.82 (3)	1.88 (4)	2.686 (3)	170 (4)
O8—H1BB···O2^vi	0.82 (3)	2.16 (3)	2.962 (3)	167 (4)
O7—H2BB···O9ⁱⁱ	0.82 (2)	2.055 (10)	2.862 (4)	168 (4)
O7—H2AA···O1	0.81 (3)	1.84 (3)	2.641 (3)	169 (4)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x+2, y+1/2, −z+3/2; (iv) −x+2, y−1/2, −z+3/2; (v) x, y−1, z; (vi) x, y+1, z.

Acknowledgements

The authors acknowledge financial support from the Science Foundation of Maoming University (grant No. 208033).

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kritagawa, S. & Kondo, M. (1998). Bull. Chem. Soc. Jpn, 71, 1739–1753. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yaghi, O. M., Li, H. & Groy, T. L. (1996). J. Am. Chem. Soc., 118, 9096–9101. CSD CrossRef CAS Web of Science Google Scholar
Zhang, Y., Jianmin, L., Min, Z., Wang, Q. & Wu, X. (1998). Chem. Lett., 27, 1051–1052. Web of Science CSD CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.