Bis[μ-2-(2-carboxyl­atophen­yl)acetato]-κ3O1,O1′:O2;κ3O2:O1,O1′-bis­[aqua­(1,10-phenanthroline-κ2N,N′)nickel(II)]

Li, F.; Zeng, H.; Yan, Z.; Li, T.

doi:10.1107/S1600536809018339

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m681

doi:10.1107/S1600536809018339

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Bis[μ-2-(2-carboxylatophenyl)acetato]-κ³O¹,O^1′:O²;κ³O²:O¹,O^1′-bis[aqua(1,10-phenanthroline-κ²N,N′)nickel(II)]

Feng Li,^a Huifang Zeng,^a Zhaowei Yan ^a and Taohai Li ^a ^*

^aCollege of Chemistry, Key Laboratory of Environmentally Friendly Chemistry and Applications of the Ministry of Education, Xiangtan University, Hunan 411105, People's Republic of China
^*Correspondence e-mail: hnlth@xtu.edu.cn

(Received 20 April 2009; accepted 14 May 2009; online 23 May 2009)

The title compound, [Ni₂(C₉H₆O₄)₂(C₁₂H₈N₂)₂(H₂O)₂], is isostructural with the Zn^II analogue. Each Ni^II atom is coordinated in a distorted octahedral geometry by three O atoms from two homophthalate anions, one aqua O atom and two 1,10-phenanthroline N atoms. The two Ni^II atoms are linked by two bridging homophthalate dianions into a centrosymmetric dinuclear unit. The dinuclear units are linked into one-dimensional ladder-like chains along [100] by O—H⋯O hydrogen bonds between the coordinated water molecules and one of the O atoms of the carboxylatomethyl group.

Related literature

For the Zn^II analogue, see: He et al. (2006 ); Sun (2006 ).

Experimental

Crystal data

[Ni₂(C₉H₆O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]
M_r = 870.14
Monoclinic, P 2₁ /c
a = 8.819 (3) Å
b = 19.432 (6) Å
c = 12.898 (3) Å
β = 122.900 (17)°
V = 1855.8 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 173 K
0.45 × 0.40 × 0.20 mm

Data collection

Rigaku Mercury70 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2001 ) T_min = 0.618, T_max = 0.806
14201 measured reflections
4232 independent reflections
3900 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.083
S = 1.05
4232 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O1ⁱ	0.84	1.87	2.653 (2)	155
O1W—H1WB⋯O4ⁱⁱ	0.83	1.88	2.7108 (17)	175
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y, -z+1.

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018339/bi2368sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018339/bi2368Isup2.hkl

checkCIF report

Comment top

The title compound is isostructural with its Zn^II analogue (He et al., 2006; Sun, 2006). The asymmetric unit consitsts of one Ni^II atom, one 1,10-phenanthroline (phen) ligan, one homophthalate dianion (hpht^2-) and a coordinated water molecule. The Ni^II atom is six-coordinated by two N atoms from phen and four O atoms, three from two hpht^2- anions and one from coordinated H₂O, in a distorted octahedron coordination geometry (Table 1). In the hpht^2- ligand, the carboxylate group coordinates in a monodentate manner to Ni^II while the ethylcarboxylate group coordinates in a bidentate manner to another Ni^II atom. Two hpht^2- ions link two Ni^II atoms to form a dinuclear complex across a centre of inversion. Such units are linked to form one-dimensional ladder-like chains along [100] by O—H···O hydrogen bonds from the coordinated water molecule to one of ethylcarboxyl O atoms. π–π interactions are formed between phen units in adjacent chains.

Related literature top

For the Zn^II analogue, see: He et al. (2006); Sun (2006).

Experimental top

Homophthalic acid (H₂hpht; 0.0275 g, 0.15 mmol), 1,10-phenanthroline (phen; 0.030 g, 0.15 mmol) and Ni(NO₃)₂.6H₂O (0.044 g, 0.15 mmol) were put in 10 ml distilled H₂O and the pH was adjusted to about 4.2 by addind dilute NaOH aqueous solution. The mixture was sealed in a 25 ml Teflon-lined autoclave and heated to 433 K for 3 days, then slowly cooled to room temperature. Red prism crystals were collected and washed with distilled water (yield: 51%)

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular unit showing displacement ellipsoids drawn at the 30% probability level. H atoms are ommited. Symetry code: (A) -x, -y, 1 -z.
	Fig. 2. One-dimensional ladder-like chain formed along [100] by O—H···O hydrogen bonding (dashed lines). Part of the phen ligand and all H atoms that bonded to C atoms are omitted for clarity.

Bis[µ-2-(2-carboxylatophenyl)acetato]- κ³O¹,O^1':O²; κ³O²:O¹,O^1'-bis[aqua(1,10-phenanthroline- κ²N,N')nickel(II)] top

Crystal data top

[Ni₂(C₉H₆O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]	F(000) = 896
M_r = 870.14	D_x = 1.557 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5071 reflections
a = 8.819 (3) Å	θ = 3.1–27.5°
b = 19.432 (6) Å	µ = 1.08 mm⁻¹
c = 12.898 (3) Å	T = 173 K
β = 122.900 (17)°	Prism, green
V = 1855.8 (10) Å³	0.45 × 0.40 × 0.20 mm
Z = 2

Data collection top

Rigaku Mercury70 CCD diffractometer	4232 independent reflections
Radiation source: fine-focus sealed tube	3900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2001)	h = −11→10
T_min = 0.618, T_max = 0.806	k = −25→25
14201 measured reflections	l = −8→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0409P)² + 0.7079P] where P = (F_o² + 2F_c²)/3
4232 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Ni₂(C₉H₆O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]	V = 1855.8 (10) Å³
M_r = 870.14	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.819 (3) Å	µ = 1.08 mm⁻¹
b = 19.432 (6) Å	T = 173 K
c = 12.898 (3) Å	0.45 × 0.40 × 0.20 mm
β = 122.900 (17)°

Data collection top

Rigaku Mercury70 CCD diffractometer	4232 independent reflections
Absorption correction: multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2001)	3900 reflections with I > 2σ(I)
T_min = 0.618, T_max = 0.806	R_int = 0.021
14201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.05	Δρ_max = 0.43 e Å⁻³
4232 reflections	Δρ_min = −0.35 e Å⁻³
262 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
Ni1	0.44081 (3)	−0.039291 (11)	0.673702 (19)	0.03024 (8)
O1	−0.33605 (19)	0.17448 (7)	0.51356 (14)	0.0502 (4)
N1	0.6408 (2)	0.03318 (7)	0.77780 (14)	0.0345 (3)
C1	−0.2231 (2)	0.15639 (8)	0.48860 (15)	0.0314 (3)
O2	−0.25662 (17)	0.11526 (7)	0.40350 (12)	0.0435 (3)
N2	0.52689 (19)	−0.07298 (7)	0.84877 (13)	0.0340 (3)
C2	−0.0352 (2)	0.18683 (8)	0.56453 (15)	0.0304 (3)
O3	0.23654 (17)	0.03212 (6)	0.64245 (12)	0.0364 (3)
C3	−0.0064 (3)	0.23714 (9)	0.65075 (17)	0.0400 (4)
H3	−0.1037	0.2502	0.6584	0.048*
O4	0.31651 (16)	0.02133 (6)	0.50972 (11)	0.0348 (3)
C4	0.1591 (3)	0.26839 (10)	0.72498 (19)	0.0497 (5)
H4	0.1761	0.3015	0.7847	0.060*
C5	0.2996 (3)	0.25140 (11)	0.7122 (2)	0.0534 (5)
H5	0.4133	0.2736	0.7613	0.064*
C6	0.2739 (3)	0.20201 (11)	0.6275 (2)	0.0485 (5)
H6	0.3715	0.1908	0.6190	0.058*
C7	0.1087 (2)	0.16760 (9)	0.55342 (16)	0.0340 (4)
C8	0.1050 (2)	0.11111 (10)	0.47180 (16)	0.0389 (4)
H8A	−0.0204	0.0944	0.4169	0.047*
H8B	0.1451	0.1299	0.4192	0.047*
C9	0.2252 (2)	0.05161 (9)	0.54613 (16)	0.0306 (3)
C10	0.6981 (3)	0.08452 (10)	0.74036 (19)	0.0448 (4)
H10	0.6441	0.0910	0.6542	0.054*
C11	0.8343 (3)	0.12948 (11)	0.8218 (2)	0.0521 (5)
H11	0.8714	0.1659	0.7913	0.062*
C12	0.9141 (3)	0.12072 (11)	0.9459 (2)	0.0483 (5)
H12	1.0071	0.1511	1.0024	0.058*
C13	0.8583 (2)	0.06661 (10)	0.99009 (17)	0.0390 (4)
C14	0.9333 (3)	0.05242 (11)	1.11804 (19)	0.0475 (5)
H14	1.0284	0.0806	1.1788	0.057*
C15	0.8722 (3)	0.00016 (11)	1.15414 (17)	0.0472 (5)
H15	0.9228	−0.0073	1.2397	0.057*
C16	0.7318 (3)	−0.04433 (9)	1.06539 (17)	0.0386 (4)
C17	0.6650 (3)	−0.10109 (11)	1.09668 (18)	0.0473 (5)
H17	0.7111	−0.1112	1.1808	0.057*
C18	0.5337 (3)	−0.14141 (11)	1.00544 (19)	0.0496 (5)
H18	0.4877	−0.1798	1.0256	0.060*
C19	0.4669 (3)	−0.12587 (10)	0.88166 (18)	0.0428 (4)
H19	0.3752	−0.1543	0.8190	0.051*
C20	0.7199 (2)	0.02413 (9)	0.90086 (16)	0.0323 (3)
C21	0.6584 (2)	−0.03289 (8)	0.94044 (16)	0.0320 (3)
O1W	0.60875 (16)	−0.09246 (6)	0.63816 (12)	0.0362 (3)
H1WA	0.5459	−0.1231	0.5868	0.060*
H1WB	0.6287	−0.0686	0.5935	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02846 (13)	0.03614 (13)	0.02636 (13)	−0.00226 (8)	0.01504 (10)	−0.00119 (8)
O1	0.0441 (8)	0.0540 (8)	0.0621 (9)	−0.0049 (6)	0.0350 (7)	−0.0166 (7)
N1	0.0306 (7)	0.0422 (8)	0.0293 (7)	−0.0014 (6)	0.0153 (6)	0.0026 (6)
C1	0.0342 (8)	0.0300 (7)	0.0306 (8)	−0.0002 (6)	0.0181 (7)	0.0024 (6)
O2	0.0400 (7)	0.0534 (8)	0.0438 (8)	−0.0164 (6)	0.0272 (6)	−0.0193 (6)
N2	0.0342 (7)	0.0387 (7)	0.0302 (7)	−0.0011 (6)	0.0181 (6)	0.0004 (6)
C2	0.0357 (8)	0.0257 (7)	0.0281 (8)	−0.0009 (6)	0.0162 (7)	0.0020 (6)
O3	0.0403 (7)	0.0432 (6)	0.0314 (6)	0.0010 (5)	0.0231 (6)	−0.0005 (5)
C3	0.0523 (11)	0.0305 (8)	0.0396 (10)	−0.0026 (7)	0.0265 (9)	−0.0046 (7)
O4	0.0327 (6)	0.0443 (6)	0.0325 (6)	0.0047 (5)	0.0211 (5)	0.0013 (5)
C4	0.0623 (13)	0.0335 (9)	0.0437 (11)	−0.0103 (9)	0.0226 (10)	−0.0102 (8)
C5	0.0465 (11)	0.0453 (10)	0.0509 (12)	−0.0151 (9)	0.0151 (10)	−0.0049 (9)
C6	0.0356 (10)	0.0530 (11)	0.0516 (12)	−0.0046 (8)	0.0203 (9)	−0.0003 (10)
C7	0.0339 (8)	0.0347 (8)	0.0304 (8)	0.0009 (6)	0.0154 (7)	0.0032 (7)
C8	0.0343 (9)	0.0526 (10)	0.0292 (9)	0.0098 (8)	0.0169 (8)	0.0005 (8)
C9	0.0259 (8)	0.0381 (8)	0.0276 (8)	−0.0046 (6)	0.0145 (7)	−0.0063 (7)
C10	0.0437 (10)	0.0504 (10)	0.0389 (10)	−0.0055 (8)	0.0214 (9)	0.0057 (8)
C11	0.0544 (12)	0.0495 (11)	0.0546 (13)	−0.0147 (9)	0.0311 (11)	−0.0018 (10)
C12	0.0457 (11)	0.0481 (11)	0.0502 (12)	−0.0130 (9)	0.0254 (10)	−0.0132 (9)
C13	0.0345 (9)	0.0448 (9)	0.0363 (10)	−0.0027 (7)	0.0184 (8)	−0.0095 (8)
C14	0.0440 (11)	0.0577 (12)	0.0330 (10)	−0.0044 (9)	0.0158 (9)	−0.0140 (9)
C15	0.0497 (11)	0.0617 (12)	0.0252 (9)	0.0009 (9)	0.0170 (8)	−0.0058 (8)
C16	0.0401 (10)	0.0478 (10)	0.0302 (9)	0.0060 (8)	0.0206 (8)	0.0002 (7)
C17	0.0564 (12)	0.0577 (12)	0.0330 (10)	0.0054 (10)	0.0276 (10)	0.0077 (9)
C18	0.0598 (13)	0.0514 (11)	0.0442 (11)	−0.0019 (9)	0.0325 (10)	0.0096 (9)
C19	0.0454 (10)	0.0456 (10)	0.0392 (10)	−0.0060 (8)	0.0242 (9)	0.0023 (8)
C20	0.0274 (8)	0.0397 (8)	0.0289 (8)	0.0011 (6)	0.0148 (7)	−0.0018 (7)
C21	0.0284 (8)	0.0374 (8)	0.0308 (9)	0.0036 (6)	0.0165 (7)	−0.0021 (7)
O1W	0.0328 (6)	0.0400 (6)	0.0381 (7)	0.0055 (5)	0.0207 (6)	0.0077 (5)

Geometric parameters (Å, º) top

Ni1—O2ⁱ	2.0130 (13)	C7—C8	1.509 (2)
Ni1—O1W	2.0515 (13)	C8—C9	1.508 (2)
Ni1—N2	2.0595 (15)	C8—H8A	0.990
Ni1—N1	2.0794 (16)	C8—H8B	0.990
Ni1—O4	2.1316 (13)	C10—C11	1.393 (3)
Ni1—O3	2.1319 (14)	C10—H10	0.950
O1—C1	1.252 (2)	C11—C12	1.365 (3)
N1—C10	1.323 (2)	C11—H11	0.950
N1—C20	1.354 (2)	C12—C13	1.406 (3)
C1—O2	1.256 (2)	C12—H12	0.950
C1—C2	1.514 (2)	C13—C20	1.403 (2)
O2—Ni1ⁱ	2.0130 (13)	C13—C14	1.432 (3)
N2—C19	1.327 (2)	C14—C15	1.346 (3)
N2—C21	1.364 (2)	C14—H14	0.950
C2—C3	1.397 (2)	C15—C16	1.432 (3)
C2—C7	1.403 (2)	C15—H15	0.950
O3—C9	1.250 (2)	C16—C21	1.390 (3)
C3—C4	1.377 (3)	C16—C17	1.409 (3)
C3—H3	0.950	C17—C18	1.363 (3)
O4—C9	1.275 (2)	C17—H17	0.950
C4—C5	1.376 (3)	C18—C19	1.402 (3)
C4—H4	0.950	C18—H18	0.950
C5—C6	1.377 (3)	C19—H19	0.950
C5—H5	0.950	C20—C21	1.443 (2)
C6—C7	1.404 (3)	O1W—H1WA	0.837
C6—H6	0.950	O1W—H1WB	0.828

O2ⁱ—Ni1—O1W	90.38 (6)	C7—C8—H8A	109.2
O2ⁱ—Ni1—N2	91.55 (6)	C9—C8—H8B	109.2
O1W—Ni1—N2	101.77 (6)	C7—C8—H8B	109.2
O2ⁱ—Ni1—N1	171.71 (6)	H8A—C8—H8B	107.9
O1W—Ni1—N1	91.33 (6)	O3—C9—O4	120.04 (16)
N2—Ni1—N1	80.16 (6)	O3—C9—C8	120.90 (15)
O2ⁱ—Ni1—O4	94.16 (6)	O4—C9—C8	119.06 (15)
O1W—Ni1—O4	95.81 (5)	N1—C10—C11	122.82 (19)
N2—Ni1—O4	161.47 (5)	N1—C10—H10	118.6
N1—Ni1—O4	93.73 (6)	C11—C10—H10	118.6
O2ⁱ—Ni1—O3	90.68 (6)	C12—C11—C10	119.36 (19)
O1W—Ni1—O3	157.53 (5)	C12—C11—H11	120.3
N2—Ni1—O3	100.64 (5)	C10—C11—H11	120.3
N1—Ni1—O3	90.83 (6)	C11—C12—C13	119.84 (18)
O4—Ni1—O3	61.73 (5)	C11—C12—H12	120.1
C10—N1—C20	118.06 (16)	C13—C12—H12	120.1
C10—N1—Ni1	129.31 (13)	C20—C13—C12	116.59 (17)
C20—N1—Ni1	112.64 (11)	C20—C13—C14	118.91 (18)
O1—C1—O2	124.09 (16)	C12—C13—C14	124.50 (18)
O1—C1—C2	117.91 (15)	C15—C14—C13	121.51 (18)
O2—C1—C2	118.00 (15)	C15—C14—H14	119.2
C1—O2—Ni1ⁱ	129.98 (11)	C13—C14—H14	119.2
C19—N2—C21	117.66 (16)	C14—C15—C16	120.91 (18)
C19—N2—Ni1	128.56 (13)	C14—C15—H15	119.5
C21—N2—Ni1	113.73 (11)	C16—C15—H15	119.5
C3—C2—C7	118.98 (16)	C21—C16—C17	116.94 (18)
C3—C2—C1	116.77 (15)	C21—C16—C15	119.12 (17)
C7—C2—C1	124.25 (15)	C17—C16—C15	123.92 (18)
C9—O3—Ni1	89.34 (10)	C18—C17—C16	119.59 (18)
C4—C3—C2	121.85 (18)	C18—C17—H17	120.2
C4—C3—H3	119.1	C16—C17—H17	120.2
C2—C3—H3	119.1	C17—C18—C19	119.58 (19)
C9—O4—Ni1	88.68 (10)	C17—C18—H18	120.2
C5—C4—C3	119.61 (19)	C19—C18—H18	120.2
C5—C4—H4	120.2	N2—C19—C18	122.49 (18)
C3—C4—H4	120.2	N2—C19—H19	118.8
C4—C5—C6	119.43 (19)	C18—C19—H19	118.8
C4—C5—H5	120.3	N1—C20—C13	123.33 (16)
C6—C5—H5	120.3	N1—C20—C21	117.46 (15)
C5—C6—C7	122.33 (19)	C13—C20—C21	119.21 (16)
C5—C6—H6	118.8	N2—C21—C16	123.73 (16)
C7—C6—H6	118.8	N2—C21—C20	115.96 (15)
C2—C7—C6	117.74 (17)	C16—C21—C20	120.31 (16)
C2—C7—C8	125.94 (16)	Ni1—O1W—H1WA	106.6
C6—C7—C8	116.28 (16)	Ni1—O1W—H1WB	109.0
C9—C8—C7	111.88 (14)	H1WA—O1W—H1WB	98.5
C9—C8—H8A	109.2

O1W—Ni1—N1—C10	76.39 (17)	C2—C7—C8—C9	−112.08 (19)
N2—Ni1—N1—C10	178.11 (18)	C6—C7—C8—C9	65.6 (2)
O4—Ni1—N1—C10	−19.52 (17)	Ni1—O3—C9—O4	4.62 (16)
O3—Ni1—N1—C10	−81.24 (17)	Ni1—O3—C9—C8	−175.03 (14)
O1W—Ni1—N1—C20	−103.35 (12)	Ni1—O4—C9—O3	−4.62 (16)
N2—Ni1—N1—C20	−1.63 (12)	Ni1—O4—C9—C8	175.04 (14)
O4—Ni1—N1—C20	160.74 (12)	C7—C8—C9—O3	38.4 (2)
O3—Ni1—N1—C20	99.02 (12)	C7—C8—C9—O4	−141.28 (16)
O1—C1—O2—Ni1ⁱ	−26.5 (3)	C20—N1—C10—C11	−0.5 (3)
C2—C1—O2—Ni1ⁱ	154.47 (12)	Ni1—N1—C10—C11	179.76 (15)
O2ⁱ—Ni1—N2—C19	−0.48 (16)	N1—C10—C11—C12	0.3 (3)
O1W—Ni1—N2—C19	−91.19 (16)	C10—C11—C12—C13	0.0 (3)
N1—Ni1—N2—C19	179.50 (17)	C11—C12—C13—C20	−0.2 (3)
O4—Ni1—N2—C19	107.5 (2)	C11—C12—C13—C14	179.5 (2)
O3—Ni1—N2—C19	90.51 (16)	C20—C13—C14—C15	−1.0 (3)
O2ⁱ—Ni1—N2—C21	−177.86 (12)	C12—C13—C14—C15	179.2 (2)
O1W—Ni1—N2—C21	91.43 (12)	C13—C14—C15—C16	1.4 (3)
N1—Ni1—N2—C21	2.12 (11)	C14—C15—C16—C21	−0.1 (3)
O4—Ni1—N2—C21	−69.8 (2)	C14—C15—C16—C17	178.2 (2)
O3—Ni1—N2—C21	−86.87 (12)	C21—C16—C17—C18	−0.2 (3)
O1—C1—C2—C3	−4.9 (2)	C15—C16—C17—C18	−178.54 (19)
O2—C1—C2—C3	174.24 (16)	C16—C17—C18—C19	0.0 (3)
O1—C1—C2—C7	175.03 (16)	C21—N2—C19—C18	−0.1 (3)
O2—C1—C2—C7	−5.9 (2)	Ni1—N2—C19—C18	−177.39 (15)
O2ⁱ—Ni1—O3—C9	−97.07 (10)	C17—C18—C19—N2	0.2 (3)
O1W—Ni1—O3—C9	−4.43 (19)	C10—N1—C20—C13	0.4 (3)
N2—Ni1—O3—C9	171.22 (10)	Ni1—N1—C20—C13	−179.87 (13)
N1—Ni1—O3—C9	91.08 (11)	C10—N1—C20—C21	−178.83 (16)
O4—Ni1—O3—C9	−2.71 (9)	Ni1—N1—C20—C21	0.94 (19)
C7—C2—C3—C4	0.0 (3)	C12—C13—C20—N1	0.0 (3)
C1—C2—C3—C4	179.96 (16)	C14—C13—C20—N1	−179.76 (17)
O2ⁱ—Ni1—O4—C9	91.19 (10)	C12—C13—C20—C21	179.15 (16)
O1W—Ni1—O4—C9	−178.00 (10)	C14—C13—C20—C21	−0.6 (3)
N2—Ni1—O4—C9	−16.4 (2)	C19—N2—C21—C16	−0.2 (3)
N1—Ni1—O4—C9	−86.27 (10)	Ni1—N2—C21—C16	177.54 (13)
O3—Ni1—O4—C9	2.66 (9)	C19—N2—C21—C20	−179.95 (15)
C2—C3—C4—C5	1.9 (3)	Ni1—N2—C21—C20	−2.26 (18)
C3—C4—C5—C6	−1.7 (3)	C17—C16—C21—N2	0.3 (3)
C4—C5—C6—C7	−0.4 (3)	C15—C16—C21—N2	178.70 (17)
C3—C2—C7—C6	−2.1 (2)	C17—C16—C21—C20	−179.90 (16)
C1—C2—C7—C6	178.01 (16)	C15—C16—C21—C20	−1.5 (3)
C3—C2—C7—C8	175.58 (16)	N1—C20—C21—N2	0.9 (2)
C1—C2—C7—C8	−4.3 (3)	C13—C20—C21—N2	−178.35 (15)
C5—C6—C7—C2	2.3 (3)	N1—C20—C21—C16	−178.93 (16)
C5—C6—C7—C8	−175.61 (19)	C13—C20—C21—C16	1.8 (2)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O1ⁱ	0.84	1.87	2.653 (2)	155
O1W—H1WB···O4ⁱⁱ	0.83	1.88	2.7108 (17)	175

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni₂(C₉H₆O₄)₂(C₁₂H₈N₂)₂(H₂O)₂]
M_r	870.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.819 (3), 19.432 (6), 12.898 (3)
β (°)	122.900 (17)
V (Å³)	1855.8 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.45 × 0.40 × 0.20

Data collection
Diffractometer	Rigaku Mercury70 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Molecular Structure Corporation & Rigaku, 2001)
T_min, T_max	0.618, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	14201, 4232, 3900
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.05
No. of reflections	4232
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.35

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 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
O1W—H1WA···O1ⁱ	0.84	1.87	2.653 (2)	155.3
O1W—H1WB···O4ⁱⁱ	0.83	1.88	2.7108 (17)	175.0

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1.

References

He, J. R., Wang, Y. L., Bi, W. H. & Zhu, X. D. (2006). J. Mol. Struct. 787, 63–68. Web of Science CSD CrossRef CAS Google Scholar
Molecular Structure Corporation & Rigaku (2001). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, J.-H. (2006). Acta Cryst. E62, m2799–m2801. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 6| June 2009| Page m681

doi:10.1107/S1600536809018339

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