Diaqua­[N,N′-bis­(4-methoxy­benz­yl)-2,2′-(ethane-1,2-diyldiimino)diacetato]nickel(II) sesquihydrate

Zhang, M.; Song, X.; Su, P.; Meng, X.

doi:10.1107/S1600536807060849

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Diaqua[N,N′-bis(4-methoxybenzyl)-2,2′-(ethane-1,2-diyldiimino)diacetato]nickel(II) sesquihydrate

M. Zhang, X. Song, P. Su and X. Meng

In the title compound, [Ni(C₂₂H₂₆N₂O₆)(H₂O)₂]·1.5H₂O, the Ni^II ion is in a slightly distorted octahedral coordination enviroment formed by an N₂O₄ donor set. In the crystal structure, intermolecular O—H

O and C—H

O hydrogen bonds and C—H

π interactions connect molecules into a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060849/lh2570sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060849/lh2570Isup2.hkl Contains datablock I

CCDC reference: 672759

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R factor = 0.043
wR factor = 0.133
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.50 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      25.00 Perc.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of N1     .....          R
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     .....          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          9

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

We have previously synthesized and characterized Ni, Zn and Cd complexes using the ligand [N, N'-bis(4-methoxylbenzyl) ethane -1,2-diyldiimino] diacetate (H₂L) (Zhang, Lan et al., 2007; Zhang, Weng, Hu et al., 2007; Zhang, Weng & Xu 2007; Xu et al., 2004). As part of our continuing studies of these types of complexes, we report the crystal structure of the title complex (I).

In (I), the Ni^II ion is in a slightly distorted octahedral coordination environment formed by an N₂O₄ donor set (Fig.1). There are no significant differences between the bond lengths and angles around the central nickel atom in and that of earlier reported analogs. In the crystal structure (Fig 2) O—H···O, C—H···O hydrogen bonds and C—H···π interaction, link molecules into a three-dimensional network.

Related literature top

For related literature, see: Zhang, Lan et al. (2007); Zhang, Weng, Hu et al. (2007); Zhang, Weng & Xu (2007); Xu et al. (2004). Cg1 is the centroid of the C16–C21 ring.

Experimental top

The ligand [N,N'-bis(4-methoxylbenzyl)ethane-1,2-diyldiimino] diacetate(H₂L) and its nickel complex were prepared according to the literature method (Xu et al., 2004). Crystals were obtained by slow evaporation (three weeks) of a methanol solution (15 ml) of the title complex (0.046 g, 0.1 mmol).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure showing the formation of a three-dimensional network. Dashed lines denote hydrogen bonds.

Diaqua[N,N'-bis(4-methoxybenzyl)-2,2'-(ethane-1,2- diyldiimino)diacetato]nickel(II) sesquihydrate top

Crystal data top

[Ni(C₂₂H₂₆N₂O₆)(H₂O)₂]·1.5H₂O	F(000) = 2264
M_r = 536.20	D_x = 1.446 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5321 reflections
a = 25.1393 (14) Å	θ = 1.6–26.9°
b = 8.1256 (4) Å	µ = 0.84 mm⁻¹
c = 26.6925 (15) Å	T = 294 K
β = 114.248 (2)°	Block, blue
V = 4971.5 (5) Å³	0.30 × 0.23 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4279 reflections with I > 2σ(I)
Radiation source: fine focus sealed Siemens Mo tube	R_int = 0.056
Graphite monochromator	θ_max = 27.0°, θ_min = 1.7°
0.3° wide ω exposures scans	h = −32→31
26930 measured reflections	k = −10→10
5429 independent reflections	l = −33→34

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0925P)²] where P = (F_o² + 2F_c²)/3
5429 reflections	(Δ/σ)_max = 0.001
337 parameters	Δρ_max = 0.45 e Å⁻³
9 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Ni(C₂₂H₂₆N₂O₆)(H₂O)₂]·1.5H₂O	V = 4971.5 (5) Å³
M_r = 536.20	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.1393 (14) Å	µ = 0.84 mm⁻¹
b = 8.1256 (4) Å	T = 294 K
c = 26.6925 (15) Å	0.30 × 0.23 × 0.20 mm
β = 114.248 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4279 reflections with I > 2σ(I)
26930 measured reflections	R_int = 0.056
5429 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	9 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.45 e Å⁻³
5429 reflections	Δρ_min = −0.36 e Å⁻³
337 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)
Ni	0.177788 (10)	0.49923 (3)	0.223662 (10)	0.03190 (12)
C1	0.08623 (9)	0.5097 (2)	0.26158 (10)	0.0371 (5)
H1A	0.0816	0.6283	0.2595	0.044*
H1B	0.0669	0.4671	0.2838	0.044*
C2	0.05859 (9)	0.4373 (3)	0.20478 (9)	0.0388 (5)
H2A	0.0611	0.3182	0.2072	0.047*
H2B	0.0176	0.4673	0.1879	0.047*
C3	0.18198 (9)	0.5916 (3)	0.32888 (8)	0.0384 (5)
H3A	0.2204	0.5493	0.3520	0.046*
H3B	0.1616	0.6145	0.3521	0.046*
C4	0.18819 (9)	0.7496 (3)	0.30125 (9)	0.0395 (5)
C5	0.16049 (9)	0.2968 (3)	0.31155 (9)	0.0384 (5)
H5A	0.2017	0.2727	0.3239	0.046*
H5B	0.1393	0.2194	0.2825	0.046*
C6	0.14326 (9)	0.2674 (3)	0.35899 (9)	0.0375 (5)
C7	0.08884 (9)	0.2062 (3)	0.35051 (9)	0.0406 (5)
H7	0.0621	0.1847	0.3148	0.049*
C8	0.07307 (10)	0.1761 (3)	0.39378 (9)	0.0406 (5)
H8	0.0363	0.1348	0.3871	0.049*
C9	0.11248 (10)	0.2080 (3)	0.44652 (9)	0.0472 (6)
C10	0.16688 (11)	0.2712 (4)	0.45653 (11)	0.0611 (8)
H10	0.1931	0.2955	0.4922	0.073*
C11	0.18194 (10)	0.2981 (4)	0.41266 (10)	0.0549 (7)
H11	0.2190	0.3378	0.4195	0.066*
C12	0.05006 (11)	0.0964 (4)	0.48656 (11)	0.0599 (7)
H12A	0.0169	0.1655	0.4674	0.090*
H12B	0.0516	0.0699	0.5222	0.090*
H12C	0.0466	−0.0030	0.4661	0.090*
C13	0.08348 (9)	0.3750 (3)	0.12824 (9)	0.0415 (5)
H13A	0.0920	0.4271	0.0997	0.050*
H13B	0.0438	0.3336	0.1116	0.050*
C14	0.12553 (9)	0.2309 (3)	0.15258 (10)	0.0423 (5)
C15	0.06626 (9)	0.6627 (3)	0.14556 (9)	0.0392 (5)
H15A	0.0872	0.6943	0.1236	0.047*
H15B	0.0761	0.7420	0.1752	0.047*
C16	0.00181 (9)	0.6764 (3)	0.11018 (9)	0.0394 (5)
C17	−0.02254 (10)	0.6239 (4)	0.05617 (9)	0.0529 (6)
H17	0.0016	0.5790	0.0411	0.063*
C18	−0.08187 (11)	0.6362 (4)	0.02370 (10)	0.0601 (7)
H18	−0.0972	0.5967	−0.0122	0.072*
C19	−0.11784 (10)	0.7070 (3)	0.04483 (11)	0.0532 (6)
C20	−0.09445 (10)	0.7631 (3)	0.09848 (10)	0.0481 (6)
H20	−0.1185	0.8121	0.1129	0.058*
C21	−0.03585 (10)	0.7467 (3)	0.13052 (9)	0.0426 (5)
H21	−0.0209	0.7835	0.1667	0.051*
C22	−0.20177 (13)	0.6894 (6)	−0.04023 (13)	0.1024 (14)
H22A	−0.1866	0.7626	−0.0594	0.154*
H22B	−0.2434	0.7019	−0.0543	0.154*
H22C	−0.1925	0.5779	−0.0455	0.154*
N1	0.14956 (7)	0.4672 (2)	0.28780 (7)	0.0312 (4)
N2	0.08809 (8)	0.49765 (18)	0.17022 (8)	0.0331 (4)
O1	0.18227 (6)	0.73640 (17)	0.25161 (6)	0.0361 (3)
O2	0.19946 (9)	0.8785 (2)	0.32799 (8)	0.0633 (5)
O3	0.10204 (8)	0.1810 (3)	0.49259 (7)	0.0660 (6)
O4	0.16957 (6)	0.25788 (17)	0.19711 (6)	0.0363 (3)
O5	0.11420 (8)	0.0997 (2)	0.12718 (8)	0.0753 (6)
O6	−0.17656 (7)	0.7273 (3)	0.01645 (9)	0.0784 (7)
O7	0.26310 (6)	0.47501 (19)	0.27647 (6)	0.0326 (3)
H7A	0.2796 (10)	0.560 (2)	0.2818 (11)	0.049*
H7B	0.2772 (10)	0.405 (2)	0.2679 (10)	0.049*
O8	0.20131 (7)	0.5574 (2)	0.15954 (7)	0.0425 (4)
H8B	0.2297 (10)	0.519 (3)	0.1597 (13)	0.064*
H8A	0.1971 (12)	0.653 (2)	0.1477 (11)	0.064*
O10	0.18169 (8)	0.8511 (2)	0.10513 (7)	0.0541 (4)
H10A	0.1592 (12)	0.836 (4)	0.0748 (8)	0.081*
H10B	0.1741 (14)	0.932 (3)	0.1176 (12)	0.081*
O9	0.0732 (2)	0.9932 (4)	0.2293 (2)	0.0868 (16)	0.50
H9A	0.1124	0.9932	0.2293	0.130*	0.50
H9B	0.0502	0.9984	0.1962	0.130*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.02839 (18)	0.03414 (19)	0.03438 (18)	0.00004 (9)	0.01411 (13)	0.00305 (9)
C1	0.0288 (11)	0.0420 (13)	0.0468 (12)	0.0068 (8)	0.0222 (10)	0.0130 (9)
C2	0.0260 (10)	0.0412 (12)	0.0497 (12)	−0.0009 (9)	0.0161 (9)	0.0099 (10)
C3	0.0419 (12)	0.0422 (13)	0.0375 (10)	0.0029 (9)	0.0226 (9)	0.0001 (9)
C4	0.0372 (11)	0.0392 (12)	0.0495 (12)	0.0011 (9)	0.0253 (10)	−0.0020 (10)
C5	0.0367 (11)	0.0394 (12)	0.0442 (11)	0.0068 (9)	0.0216 (9)	0.0133 (9)
C6	0.0357 (10)	0.0391 (12)	0.0402 (11)	0.0039 (9)	0.0180 (9)	0.0125 (9)
C7	0.0388 (11)	0.0430 (13)	0.0394 (11)	−0.0021 (9)	0.0155 (9)	0.0066 (9)
C8	0.0370 (11)	0.0430 (13)	0.0447 (12)	−0.0031 (9)	0.0198 (10)	0.0070 (10)
C9	0.0458 (13)	0.0592 (16)	0.0408 (12)	−0.0032 (11)	0.0221 (10)	0.0111 (11)
C10	0.0466 (14)	0.091 (2)	0.0383 (12)	−0.0185 (14)	0.0104 (10)	0.0138 (13)
C11	0.0364 (12)	0.0805 (19)	0.0439 (12)	−0.0084 (12)	0.0126 (10)	0.0180 (12)
C12	0.0507 (15)	0.086 (2)	0.0526 (14)	−0.0012 (14)	0.0313 (12)	0.0142 (14)
C13	0.0344 (11)	0.0452 (13)	0.0367 (10)	0.0014 (9)	0.0063 (9)	0.0016 (9)
C14	0.0348 (11)	0.0406 (13)	0.0464 (12)	−0.0011 (9)	0.0116 (9)	−0.0044 (10)
C15	0.0335 (11)	0.0382 (12)	0.0449 (11)	0.0045 (9)	0.0151 (9)	0.0132 (9)
C16	0.0348 (11)	0.0415 (12)	0.0416 (11)	0.0070 (9)	0.0154 (9)	0.0128 (9)
C17	0.0433 (13)	0.0733 (18)	0.0426 (12)	0.0167 (12)	0.0181 (10)	0.0102 (12)
C18	0.0486 (14)	0.085 (2)	0.0395 (12)	0.0121 (14)	0.0111 (11)	0.0049 (13)
C19	0.0351 (12)	0.0685 (18)	0.0529 (14)	0.0058 (11)	0.0147 (11)	0.0116 (12)
C20	0.0387 (12)	0.0538 (15)	0.0579 (14)	0.0095 (10)	0.0259 (11)	0.0125 (12)
C21	0.0418 (12)	0.0451 (13)	0.0419 (11)	0.0041 (10)	0.0183 (10)	0.0077 (10)
C22	0.0467 (17)	0.175 (4)	0.0621 (19)	0.011 (2)	−0.0008 (15)	0.016 (2)
N1	0.0263 (8)	0.0344 (9)	0.0362 (9)	0.0035 (7)	0.0162 (7)	0.0067 (7)
N2	0.0276 (9)	0.0344 (10)	0.0373 (9)	0.0029 (6)	0.0132 (8)	0.0078 (7)
O1	0.0374 (8)	0.0330 (8)	0.0426 (8)	−0.0016 (6)	0.0210 (6)	0.0019 (6)
O2	0.0919 (14)	0.0448 (10)	0.0778 (12)	−0.0143 (9)	0.0598 (11)	−0.0192 (9)
O3	0.0639 (11)	0.0989 (15)	0.0404 (9)	−0.0248 (11)	0.0267 (8)	0.0083 (9)
O4	0.0310 (7)	0.0343 (8)	0.0388 (8)	0.0017 (6)	0.0097 (6)	0.0007 (6)
O5	0.0577 (11)	0.0523 (12)	0.0821 (13)	0.0061 (9)	−0.0056 (10)	−0.0270 (10)
O6	0.0323 (9)	0.126 (2)	0.0665 (12)	0.0121 (10)	0.0096 (9)	0.0082 (12)
O7	0.0276 (8)	0.0343 (8)	0.0361 (8)	0.0007 (6)	0.0134 (6)	−0.0032 (6)
O8	0.0422 (9)	0.0480 (9)	0.0447 (9)	0.0053 (8)	0.0254 (7)	0.0098 (8)
O10	0.0628 (11)	0.0548 (11)	0.0409 (9)	0.0101 (9)	0.0176 (8)	0.0019 (8)
O9	0.066 (3)	0.066 (3)	0.115 (4)	0.0022 (19)	0.023 (3)	−0.020 (2)

Geometric parameters (Å, º) top

Ni—O7	2.0352 (15)	C12—H12B	0.9600
Ni—O1	2.0529 (14)	C12—H12C	0.9600
Ni—O4	2.0666 (14)	C13—N2	1.468 (3)
Ni—O8	2.0818 (15)	C13—C14	1.532 (3)
Ni—N2	2.1159 (18)	C13—H13A	0.9700
Ni—N1	2.1212 (17)	C13—H13B	0.9700
C1—N1	1.493 (3)	C14—O5	1.232 (3)
C1—C2	1.504 (3)	C14—O4	1.267 (3)
C1—H1A	0.9700	C15—N2	1.496 (3)
C1—H1B	0.9700	C15—C16	1.508 (3)
C2—N2	1.484 (3)	C15—H15A	0.9700
C2—H2A	0.9700	C15—H15B	0.9700
C2—H2B	0.9700	C16—C17	1.382 (3)
C3—N1	1.468 (3)	C16—C21	1.393 (3)
C3—C4	1.521 (3)	C17—C18	1.387 (3)
C3—H3A	0.9700	C17—H17	0.9300
C3—H3B	0.9700	C18—C19	1.373 (4)
C4—O2	1.233 (3)	C18—H18	0.9300
C4—O1	1.276 (3)	C19—O6	1.364 (3)
C5—N1	1.500 (3)	C19—C20	1.383 (4)
C5—C6	1.516 (3)	C20—C21	1.373 (3)
C5—H5A	0.9700	C20—H20	0.9300
C5—H5B	0.9700	C21—H21	0.9300
C6—C11	1.384 (3)	C22—O6	1.413 (4)
C6—C7	1.384 (3)	C22—H22A	0.9600
C7—C8	1.388 (3)	C22—H22B	0.9600
C7—H7	0.9300	C22—H22C	0.9600
C8—C9	1.373 (3)	O7—H7A	0.791 (15)
C8—H8	0.9300	O7—H7B	0.757 (15)
C9—O3	1.376 (3)	O8—H8B	0.776 (17)
C9—C10	1.380 (3)	O8—H8A	0.832 (16)
C10—C11	1.388 (4)	O10—H10A	0.784 (17)
C10—H10	0.9300	O10—H10B	0.796 (17)
C11—H11	0.9300	O9—H9A	0.9830
C12—O3	1.426 (3)	O9—H9B	0.8345
C12—H12A	0.9600

O7—Ni—O1	87.37 (6)	H12B—C12—H12C	109.5
O7—Ni—O4	94.26 (6)	N2—C13—C14	111.77 (17)
O1—Ni—O4	176.70 (5)	N2—C13—H13A	109.3
O7—Ni—O8	90.98 (6)	C14—C13—H13A	109.3
O1—Ni—O8	95.39 (6)	N2—C13—H13B	109.3
O4—Ni—O8	87.46 (7)	C14—C13—H13B	109.3
O7—Ni—N2	173.93 (6)	H13A—C13—H13B	107.9
O1—Ni—N2	97.76 (6)	O5—C14—O4	125.5 (2)
O4—Ni—N2	80.46 (6)	O5—C14—C13	117.7 (2)
O8—Ni—N2	91.78 (7)	O4—C14—C13	116.77 (19)
O7—Ni—N1	92.06 (6)	N2—C15—C16	116.57 (18)
O1—Ni—N1	78.96 (6)	N2—C15—H15A	108.1
O4—Ni—N1	98.10 (6)	C16—C15—H15A	108.1
O8—Ni—N1	173.46 (6)	N2—C15—H15B	108.1
N2—Ni—N1	85.77 (7)	C16—C15—H15B	108.1
N1—C1—C2	110.15 (17)	H15A—C15—H15B	107.3
N1—C1—H1A	109.6	C17—C16—C21	116.9 (2)
C2—C1—H1A	109.6	C17—C16—C15	122.2 (2)
N1—C1—H1B	109.6	C21—C16—C15	120.9 (2)
C2—C1—H1B	109.6	C16—C17—C18	122.1 (2)
H1A—C1—H1B	108.1	C16—C17—H17	118.9
N2—C2—C1	110.81 (17)	C18—C17—H17	118.9
N2—C2—H2A	109.5	C19—C18—C17	119.6 (2)
C1—C2—H2A	109.5	C19—C18—H18	120.2
N2—C2—H2B	109.5	C17—C18—H18	120.2
C1—C2—H2B	109.5	O6—C19—C18	124.6 (2)
H2A—C2—H2B	108.1	O6—C19—C20	116.0 (2)
N1—C3—C4	110.80 (17)	C18—C19—C20	119.5 (2)
N1—C3—H3A	109.5	C21—C20—C19	120.3 (2)
C4—C3—H3A	109.5	C21—C20—H20	119.9
N1—C3—H3B	109.5	C19—C20—H20	119.9
C4—C3—H3B	109.5	C20—C21—C16	121.6 (2)
H3A—C3—H3B	108.1	C20—C21—H21	119.2
O2—C4—O1	125.0 (2)	C16—C21—H21	119.2
O2—C4—C3	118.8 (2)	O6—C22—H22A	109.5
O1—C4—C3	116.18 (19)	O6—C22—H22B	109.5
N1—C5—C6	115.65 (17)	H22A—C22—H22B	109.5
N1—C5—H5A	108.4	O6—C22—H22C	109.5
C6—C5—H5A	108.4	H22A—C22—H22C	109.5
N1—C5—H5B	108.4	H22B—C22—H22C	109.5
C6—C5—H5B	108.4	C3—N1—C1	110.43 (16)
H5A—C5—H5B	107.4	C3—N1—C5	111.74 (16)
C11—C6—C7	117.5 (2)	C1—N1—C5	112.73 (16)
C11—C6—C5	121.1 (2)	C3—N1—Ni	104.56 (12)
C7—C6—C5	121.5 (2)	C1—N1—Ni	103.84 (12)
C6—C7—C8	121.9 (2)	C5—N1—Ni	112.98 (12)
C6—C7—H7	119.1	C13—N2—C2	110.31 (16)
C8—C7—H7	119.1	C13—N2—C15	111.92 (17)
C9—C8—C7	119.2 (2)	C2—N2—C15	112.52 (17)
C9—C8—H8	120.4	C13—N2—Ni	104.29 (12)
C7—C8—H8	120.4	C2—N2—Ni	104.43 (12)
C8—C9—O3	124.3 (2)	C15—N2—Ni	112.83 (12)
C8—C9—C10	120.6 (2)	C4—O1—Ni	114.97 (13)
O3—C9—C10	115.1 (2)	C9—O3—C12	118.57 (19)
C9—C10—C11	119.1 (2)	C14—O4—Ni	114.31 (14)
C9—C10—H10	120.4	C19—O6—C22	118.4 (2)
C11—C10—H10	120.4	Ni—O7—H7A	111.5 (19)
C6—C11—C10	121.7 (2)	Ni—O7—H7B	110.9 (19)
C6—C11—H11	119.1	H7A—O7—H7B	116 (2)
C10—C11—H11	119.1	Ni—O8—H8B	118 (2)
O3—C12—H12A	109.5	Ni—O8—H8A	119.4 (19)
O3—C12—H12B	109.5	H8B—O8—H8A	110 (2)
H12A—C12—H12B	109.5	H10A—O10—H10B	112 (3)
O3—C12—H12C	109.5	H9A—O9—H9B	105.1
H12A—C12—H12C	109.5

N1—C1—C2—N2	−58.1 (2)	O1—Ni—N1—C1	83.25 (12)
N1—C3—C4—O2	160.3 (2)	O4—Ni—N1—C1	−95.24 (12)
N1—C3—C4—O1	−21.0 (3)	N2—Ni—N1—C1	−15.52 (12)
N1—C5—C6—C11	−88.3 (3)	O7—Ni—N1—C5	−67.38 (14)
N1—C5—C6—C7	92.9 (3)	O1—Ni—N1—C5	−154.29 (14)
C11—C6—C7—C8	0.0 (3)	O4—Ni—N1—C5	27.22 (14)
C5—C6—C7—C8	178.8 (2)	N2—Ni—N1—C5	106.94 (14)
C6—C7—C8—C9	0.1 (4)	C14—C13—N2—C2	−76.0 (2)
C7—C8—C9—O3	−179.1 (2)	C14—C13—N2—C15	157.91 (18)
C7—C8—C9—C10	0.8 (4)	C14—C13—N2—Ni	35.6 (2)
C8—C9—C10—C11	−1.7 (5)	C1—C2—N2—C13	151.50 (17)
O3—C9—C10—C11	178.2 (3)	C1—C2—N2—C15	−82.7 (2)
C7—C6—C11—C10	−0.9 (4)	C1—C2—N2—Ni	39.97 (19)
C5—C6—C11—C10	−179.7 (3)	C16—C15—N2—C13	67.1 (2)
C9—C10—C11—C6	1.8 (5)	C16—C15—N2—C2	−57.8 (2)
N2—C13—C14—O5	158.0 (2)	C16—C15—N2—Ni	−175.64 (15)
N2—C13—C14—O4	−22.7 (3)	O1—Ni—N2—C13	153.15 (13)
N2—C15—C16—C17	−80.1 (3)	O4—Ni—N2—C13	−29.66 (13)
N2—C15—C16—C21	101.4 (3)	O8—Ni—N2—C13	57.46 (13)
C21—C16—C17—C18	−1.6 (4)	N1—Ni—N2—C13	−128.61 (13)
C15—C16—C17—C18	179.8 (2)	O1—Ni—N2—C2	−91.04 (13)
C16—C17—C18—C19	2.0 (4)	O4—Ni—N2—C2	86.15 (13)
C17—C18—C19—O6	179.1 (3)	O8—Ni—N2—C2	173.27 (13)
C17—C18—C19—C20	−0.9 (4)	N1—Ni—N2—C2	−12.80 (13)
O6—C19—C20—C21	179.4 (2)	O4—Ni—N2—C15	−151.34 (15)
C18—C19—C20—C21	−0.6 (4)	O8—Ni—N2—C15	−64.22 (15)
C19—C20—C21—C16	1.0 (4)	N1—Ni—N2—C15	109.71 (15)
C17—C16—C21—C20	0.1 (3)	O2—C4—O1—Ni	169.82 (19)
C15—C16—C21—C20	178.7 (2)	C3—C4—O1—Ni	−8.7 (2)
C4—C3—N1—C1	−73.8 (2)	O8—Ni—O1—C4	−159.23 (15)
C4—C3—N1—C5	159.87 (16)	N2—Ni—O1—C4	108.24 (15)
C4—C3—N1—Ni	37.33 (18)	N1—Ni—O1—C4	24.12 (14)
C2—C1—N1—C3	153.48 (17)	C8—C9—O3—C12	7.9 (4)
C2—C1—N1—C5	−80.7 (2)	C10—C9—O3—C12	−172.0 (3)
C2—C1—N1—Ni	41.88 (18)	O5—C14—O4—Ni	174.6 (2)
C6—C5—N1—C3	60.3 (2)	C13—C14—O4—Ni	−4.6 (3)
C6—C5—N1—C1	−64.7 (2)	O7—Ni—O4—C14	−162.88 (15)
C6—C5—N1—Ni	177.91 (14)	O8—Ni—O4—C14	−72.09 (15)
O7—Ni—N1—C3	54.35 (12)	N2—Ni—O4—C14	20.14 (15)
O1—Ni—N1—C3	−32.57 (12)	N1—Ni—O4—C14	104.43 (15)
O4—Ni—N1—C3	148.95 (12)	C18—C19—O6—C22	−7.0 (5)
N2—Ni—N1—C3	−131.33 (13)	C20—C19—O6—C22	173.0 (3)
O7—Ni—N1—C1	170.16 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.79 (2)	1.98 (2)	2.769 (2)	172 (3)
O7—H7B···O1ⁱⁱ	0.76 (2)	1.90 (2)	2.656 (2)	176 (2)
O8—H8B···O2ⁱⁱ	0.78 (2)	2.03 (2)	2.787 (2)	166 (3)
O10—H10A···O3ⁱⁱⁱ	0.78 (2)	2.08 (2)	2.857 (2)	174 (3)
O10—H10B···O5^iv	0.80 (2)	2.12 (2)	2.851 (3)	152 (3)
C5—H5B···O9^v	0.97	2.49	3.430 (5)	162
C15—H15B···O9	0.97	2.52	3.451 (5)	161
O8—H8A···O10	0.83 (2)	1.91 (2)	2.731 (3)	167 (3)
C12—H12C···Cg1^vi	0.96	2.80	3.746 (3)	169

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

Experimental details

Crystal data
Chemical formula	[Ni(C₂₂H₂₆N₂O₆)(H₂O)₂]·1.5H₂O
M_r	536.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	25.1393 (14), 8.1256 (4), 26.6925 (15)
β (°)	114.248 (2)
V (Å³)	4971.5 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.30 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	26930, 5429, 4279
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.133, 1.03
No. of reflections	5429
No. of parameters	337
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.36

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Selected bond lengths (Å) top

Ni—O7	2.0352 (15)	Ni—O8	2.0818 (15)
Ni—O1	2.0529 (14)	Ni—N2	2.1159 (18)
Ni—O4	2.0666 (14)	Ni—N1	2.1212 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O4ⁱ	0.791 (15)	1.984 (16)	2.769 (2)	172 (3)
O7—H7B···O1ⁱⁱ	0.757 (15)	1.900 (16)	2.656 (2)	176 (2)
O8—H8B···O2ⁱⁱ	0.776 (17)	2.027 (16)	2.787 (2)	166 (3)
O10—H10A···O3ⁱⁱⁱ	0.784 (17)	2.076 (17)	2.857 (2)	174 (3)
O10—H10B···O5^iv	0.796 (17)	2.12 (2)	2.851 (3)	152 (3)
C5—H5B···O9^v	0.97	2.49	3.430 (5)	162.1
C15—H15B···O9	0.97	2.52	3.451 (5)	161.4
O8—H8A···O10	0.832 (16)	1.913 (17)	2.731 (3)	167 (3)
C12—H12C···Cg1^vi	0.96	2.80	3.746 (3)	169

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

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