catena-Poly[[diaqua­(2,2′-bipyridine-κ2N,N′)nickel(II)]-μ-biphenyl-2,2′-dicarboxyl­ato-κ2O:O′]

An, Z.; Niu, X.-C.

doi:10.1107/S1600536808036866

catena-Poly[[diaqua(2,2′-bipyridine-κ²N,N′)nickel(II)]-μ-biphenyl-2,2′-dicarboxylato-κ²O:O′]

In the title compound, [Ni(C₁₄H₈O₄)(C₁₀H₈N₂)(H₂O)₂]_n, the Ni^II atom is coordinated in a slightly distorted octahedral geometry by two water molecules, two N atoms from a 2,2′-bipyridine ligand and two O atoms from the carboxylate groups of two 2,2′-biphenyldicarboxylate (2,2′-dpa) ligands. The 2,2′-dpa ligand acts as a bridge between neighbouring Ni^II atoms, forming one-dimensional coordination polymers along [100]. The coordinated water molecules form hydrogen bonds to the carboxylate O atoms of 2,2′-dpa within the same coordination polymer, and one O—H

π interaction is also formed to 2,2′-dpa.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808036866/bi2317sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808036866/bi2317Isup2.hkl Contains datablock I

CCDC reference: 712304

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R factor = 0.034
wR factor = 0.088
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O5     -   H1W    ...          ?

Alert level C
            Value of measurement temperature given =   296.000
            Value of melting point given =     0.000
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C13    -   C14    ...       1.53 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C4     --  C5      ..       0.11  Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.10
           From the CIF: _reflns_number_total               3953
           Count of symmetry unique reflns         2259
           Completeness (_total/calc)            174.99%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1694
           Fraction of Friedel pairs measured     0.750
           Are heavy atom types Z>Si present        yes

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

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

Comment top

2,2'-Biphenyldicarboxylic acid (H₂dpa) has been demonstrated to be a useful ligand for constructing metal-organic frameworks (Rueff et al., 2003; Wang et al., 2006; Xu et al., 2006). The title compound is a Ni^II coordination polymer in which 2,2'-biphenyldicarboxylate (2,2'-dpa) acts as a bridging ligand.

The asymmetric unit (Fig. 1) contains one Ni^II atom coordinated by one 2,2'-bipyridine ligand, 2,2'-dpa and two water molecules. The Ni^II atom is hexacoordinated in a slightly distorted octahedral geometry by two water molecules, two N atoms from 2,2'-bipyridine, and two O atoms from carboxylate groups of two 2,2'-dpa. The 2,2'-dpa ligand acts as a bridge to link two neighboring Ni^II atoms, forming a 1-D coordination polymer along [100] (Fig. 2). Hydrogen bonds from the coordinated water molecules and the O atoms of the carboxylate groups are formed within the same coordination polymer (Fig. 3). One water molecule also forms an O—H···πi interaction to the neighbouring benzene ring of 2,2'-dpa.

Related literature top

For other metal–organic frameworks containing 2,2'-dpa, see: Rueff et al. (2003); Wang et al. (2006); Xu et al. (2006).

Experimental top

A mixture of nickel(II) chloride hexahydrate (0.1 mmol), 2,2'-bipyridine (0.1 mmol), biphenyl-2,2'-dicarboxylic acid (0.2 mmol) and H₂O (16 ml) in a 25 ml Teflon-lined stainless steel autoclave was kept at 463 K for five days. Green crystals were obtained after cooling to room temperature with a yield of 12%. Elemental analysis calculated: C 58.64, H 4.89, N 5.70%; found: C 58.62, H 4.86, N 5.65%.

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. Asymmetric unit of the title compound showing displacement ellipsoids at 30% for non-H atoms.
	Fig. 2. 1-D coordination polymer running along the [100] direction.
	Fig. 3. View of the packing along the a axis.

catena-Poly[[diaqua(2,2'-bipyridine-κ²N,N')nickel(II)]- µ-biphenyl-2,2'-dicarboxylato-κ²O:O'] top

Crystal data top

[Ni(C₁₄H₈O₄)(C₁₀H₈N₂)(H₂O)₂]	F(000) = 1016
M_r = 491.11	D_x = 1.471 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3953 reflections
a = 10.9087 (15) Å	θ = 2.1–25.1°
b = 11.214 (2) Å	µ = 0.92 mm⁻¹
c = 18.129 (3) Å	T = 296 K
V = 2217.6 (6) Å³	Block, green
Z = 4	0.42 × 0.27 × 0.19 mm

Data collection top

Bruker APEXII CCD diffractometer	3953 independent reflections
Radiation source: fine-focus sealed tube	3351 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→12
T_min = 0.699, T_max = 0.845	k = −9→13
11746 measured reflections	l = −20→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.051P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3953 reflections	Δρ_max = 0.21 e Å⁻³
310 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1694 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.042 (16)

Crystal data top

[Ni(C₁₄H₈O₄)(C₁₀H₈N₂)(H₂O)₂]	V = 2217.6 (6) Å³
M_r = 491.11	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.9087 (15) Å	µ = 0.92 mm⁻¹
b = 11.214 (2) Å	T = 296 K
c = 18.129 (3) Å	0.42 × 0.27 × 0.19 mm

Data collection top

Bruker APEXII CCD diffractometer	3953 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3351 reflections with I > 2σ(I)
T_min = 0.699, T_max = 0.845	R_int = 0.033
11746 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	Δρ_max = 0.21 e Å⁻³
S = 1.00	Δρ_min = −0.30 e Å⁻³
3953 reflections	Absolute structure: Flack (1983), 1694 Friedel pairs
310 parameters	Absolute structure parameter: 0.042 (16)
0 restraints

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	0.24756 (4)	0.69154 (3)	0.898676 (19)	0.03527 (12)
C1	0.5625 (3)	1.0010 (3)	1.06148 (16)	0.0367 (7)
C2	0.4305 (3)	1.0354 (3)	1.03948 (16)	0.0377 (8)
C3	0.4167 (4)	1.1232 (3)	0.98610 (18)	0.0525 (9)
H3	0.4864	1.1582	0.9661	0.063*
C4	0.3031 (5)	1.1602 (4)	0.9617 (2)	0.0673 (14)
H4	0.2977	1.2188	0.9255	0.081*
C5	0.1971 (4)	1.1108 (4)	0.9905 (2)	0.0616 (12)
H5	0.1208	1.1353	0.9735	0.074*
C6	0.2059 (3)	1.0243 (3)	1.04525 (19)	0.0515 (10)
H6	0.1351	0.9918	1.0656	0.062*
C7	0.3233 (3)	0.9853 (3)	1.07010 (16)	0.0386 (8)
C8	0.3257 (3)	0.9030 (3)	1.13631 (16)	0.0360 (7)
C9	0.3102 (3)	0.9525 (3)	1.20745 (18)	0.0492 (9)
H9	0.2988	1.0345	1.2110	0.059*
C10	0.3108 (4)	0.8874 (4)	1.27158 (19)	0.0552 (10)
H10	0.2954	0.9239	1.3167	0.066*
C11	0.3343 (4)	0.7687 (4)	1.26763 (18)	0.0553 (10)
H11	0.3383	0.7222	1.3101	0.066*
C12	0.3524 (3)	0.7181 (3)	1.19772 (17)	0.0469 (8)
H12	0.3706	0.6372	1.1950	0.056*
C13	0.3445 (3)	0.7820 (3)	1.13252 (16)	0.0356 (7)
C14	0.3500 (3)	0.7168 (3)	1.05824 (16)	0.0342 (7)
C15	0.4937 (3)	0.8346 (3)	0.8927 (2)	0.0509 (9)
H15	0.4958	0.8224	0.9435	0.061*
C16	0.5799 (3)	0.9085 (3)	0.8606 (2)	0.0608 (10)
H16	0.6392	0.9457	0.8894	0.073*
C17	0.5771 (4)	0.9267 (4)	0.7847 (3)	0.0678 (12)
H17	0.6337	0.9772	0.7625	0.081*
C18	0.4900 (4)	0.8695 (4)	0.7424 (2)	0.0596 (10)
H18	0.4877	0.8802	0.6915	0.071*
C19	0.4047 (3)	0.7949 (3)	0.77769 (18)	0.0401 (7)
C20	0.3066 (3)	0.7286 (3)	0.73743 (17)	0.0383 (8)
C21	0.3005 (4)	0.7230 (3)	0.65934 (18)	0.0527 (10)
H21	0.3595	0.7609	0.6306	0.063*
C22	0.2058 (4)	0.6605 (3)	0.6264 (2)	0.0587 (11)
H22	0.2007	0.6555	0.5753	0.070*
C23	0.1192 (4)	0.6058 (3)	0.66986 (18)	0.0525 (10)
H23	0.0547	0.5638	0.6486	0.063*
C24	0.1297 (3)	0.6143 (3)	0.74713 (18)	0.0451 (8)
H24	0.0705	0.5780	0.7764	0.054*
N1	0.4065 (2)	0.7797 (2)	0.85219 (14)	0.0402 (7)
N2	0.2231 (2)	0.6733 (2)	0.78055 (13)	0.0363 (6)
O1	0.28142 (19)	0.75413 (19)	1.00612 (11)	0.0407 (6)
O2	0.4185 (2)	0.6272 (2)	1.05422 (12)	0.0451 (6)
O3	0.58196 (19)	0.89368 (18)	1.07528 (12)	0.0385 (5)
O4	0.6422 (2)	1.0789 (2)	1.06222 (17)	0.0670 (8)
O5	0.1519 (2)	0.85857 (18)	0.89069 (12)	0.0394 (5)
H1W	0.187 (2)	0.895 (3)	0.9264 (15)	0.047*
H2W	0.0764 (16)	0.858 (3)	0.9025 (17)	0.047*
O6	0.3552 (2)	0.5345 (2)	0.91659 (13)	0.0466 (6)
H3W	0.302 (3)	0.484 (3)	0.9225 (18)	0.056*
H4W	0.385 (3)	0.557 (3)	0.9558 (13)	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0390 (2)	0.0344 (2)	0.0325 (2)	−0.0010 (2)	0.0015 (2)	−0.00163 (16)
C1	0.047 (2)	0.0325 (18)	0.0310 (16)	0.0033 (16)	0.0056 (14)	0.0009 (14)
C2	0.058 (2)	0.0275 (16)	0.0275 (15)	0.0093 (16)	−0.0028 (15)	−0.0034 (13)
C3	0.080 (3)	0.0377 (19)	0.0401 (19)	0.006 (2)	−0.0049 (19)	0.0003 (17)
C4	0.114 (4)	0.042 (2)	0.045 (2)	0.026 (2)	−0.033 (2)	−0.0035 (18)
C5	0.080 (3)	0.049 (2)	0.056 (2)	0.034 (2)	−0.032 (2)	−0.015 (2)
C6	0.054 (2)	0.052 (2)	0.048 (2)	0.0185 (18)	−0.0131 (16)	−0.0215 (18)
C7	0.049 (2)	0.0350 (18)	0.0319 (16)	0.0132 (15)	−0.0035 (15)	−0.0093 (14)
C8	0.0320 (17)	0.0416 (18)	0.0343 (16)	0.0010 (14)	0.0026 (14)	−0.0022 (14)
C9	0.056 (2)	0.046 (2)	0.045 (2)	0.0093 (17)	0.0060 (17)	−0.0082 (17)
C10	0.065 (2)	0.068 (3)	0.0335 (18)	−0.004 (2)	0.0110 (17)	−0.0084 (18)
C11	0.071 (3)	0.065 (3)	0.0296 (17)	−0.011 (2)	0.0051 (18)	0.0021 (17)
C12	0.059 (2)	0.0417 (19)	0.0402 (18)	−0.0088 (17)	−0.0019 (17)	0.0041 (16)
C13	0.0349 (17)	0.0436 (19)	0.0283 (15)	−0.0034 (15)	0.0040 (13)	−0.0020 (14)
C14	0.0370 (17)	0.0334 (18)	0.0321 (16)	−0.0062 (15)	0.0009 (14)	−0.0021 (14)
C15	0.0413 (19)	0.054 (2)	0.057 (2)	−0.0117 (16)	0.0082 (18)	−0.0048 (19)
C16	0.043 (2)	0.053 (2)	0.087 (3)	−0.0107 (19)	0.007 (2)	−0.002 (2)
C17	0.048 (2)	0.054 (2)	0.102 (3)	−0.013 (2)	0.015 (2)	0.019 (2)
C18	0.061 (2)	0.056 (2)	0.062 (2)	−0.002 (2)	0.016 (2)	0.018 (2)
C19	0.0407 (17)	0.0313 (17)	0.0482 (19)	0.0054 (15)	0.0106 (15)	0.0042 (15)
C20	0.0513 (19)	0.0280 (16)	0.0356 (17)	0.0079 (15)	0.0065 (15)	0.0024 (14)
C21	0.078 (3)	0.043 (2)	0.0376 (18)	0.0082 (19)	0.0099 (18)	0.0045 (16)
C22	0.096 (3)	0.050 (2)	0.0305 (17)	0.018 (2)	−0.0062 (19)	0.0007 (17)
C23	0.072 (3)	0.041 (2)	0.044 (2)	0.0062 (19)	−0.0159 (18)	−0.0114 (18)
C24	0.053 (2)	0.042 (2)	0.0401 (19)	−0.0008 (17)	−0.0012 (16)	−0.0061 (16)
N1	0.0388 (15)	0.0395 (15)	0.0423 (16)	−0.0044 (13)	0.0074 (12)	−0.0037 (13)
N2	0.0432 (16)	0.0361 (14)	0.0295 (12)	0.0032 (12)	0.0015 (11)	−0.0020 (11)
O1	0.0520 (14)	0.0380 (12)	0.0322 (11)	0.0053 (10)	−0.0061 (10)	−0.0038 (9)
O2	0.0518 (14)	0.0400 (13)	0.0436 (13)	0.0029 (12)	−0.0086 (11)	−0.0076 (11)
O3	0.0403 (12)	0.0297 (12)	0.0456 (12)	0.0018 (10)	−0.0019 (10)	0.0082 (10)
O4	0.0539 (15)	0.0333 (14)	0.114 (2)	−0.0040 (13)	0.0030 (16)	0.0071 (15)
O5	0.0418 (12)	0.0328 (12)	0.0436 (13)	0.0019 (10)	0.0014 (11)	−0.0006 (10)
O6	0.0465 (15)	0.0415 (14)	0.0519 (15)	0.0074 (11)	−0.0036 (12)	−0.0072 (12)

Geometric parameters (Å, º) top

Ni1—O3ⁱ	2.098 (2)	C13—C14	1.533 (4)
Ni1—O1	2.103 (2)	C14—O2	1.255 (4)
Ni1—O6	2.142 (2)	C14—O1	1.276 (3)
Ni1—O5	2.149 (2)	C15—N1	1.351 (4)
Ni1—N1	2.166 (3)	C15—C16	1.383 (5)
Ni1—N2	2.168 (2)	C15—H15	0.930
C1—O4	1.233 (4)	C16—C17	1.391 (6)
C1—O3	1.247 (4)	C16—H16	0.930
C1—C2	1.543 (5)	C17—C18	1.379 (6)
C2—C3	1.388 (5)	C17—H17	0.930
C2—C7	1.412 (5)	C18—C19	1.406 (5)
C3—C4	1.380 (6)	C18—H18	0.930
C3—H3	0.930	C19—N1	1.361 (4)
C4—C5	1.385 (6)	C19—C20	1.493 (5)
C4—H4	0.930	C20—N2	1.352 (4)
C5—C6	1.391 (5)	C20—C21	1.419 (4)
C5—H5	0.930	C21—C22	1.385 (6)
C6—C7	1.427 (4)	C21—H21	0.930
C6—H6	0.930	C22—C23	1.374 (5)
C7—C8	1.514 (4)	C22—H22	0.930
C8—C13	1.374 (5)	C23—C24	1.409 (5)
C8—C9	1.414 (4)	C23—H23	0.930
C9—C10	1.373 (5)	C24—N2	1.357 (4)
C9—H9	0.930	C24—H24	0.930
C10—C11	1.358 (6)	O3—Ni1ⁱⁱ	2.098 (2)
C10—H10	0.930	O5—H1W	0.86 (2)
C11—C12	1.402 (5)	O5—H2W	0.85 (2)
C11—H11	0.930	O6—H3W	0.81 (2)
C12—C13	1.385 (4)	O6—H4W	0.82 (2)
C12—H12	0.930

O3ⁱ—Ni1—O1	95.44 (8)	C8—C13—C12	118.5 (3)
O3ⁱ—Ni1—O6	93.63 (9)	C8—C13—C14	121.3 (3)
O1—Ni1—O6	92.16 (9)	C12—C13—C14	120.1 (3)
O3ⁱ—Ni1—O5	89.65 (8)	O2—C14—O1	124.7 (3)
O1—Ni1—O5	81.77 (8)	O2—C14—C13	117.1 (3)
O6—Ni1—O5	173.36 (9)	O1—C14—C13	118.1 (3)
O3ⁱ—Ni1—N1	169.97 (9)	N1—C15—C16	121.5 (4)
O1—Ni1—N1	93.86 (9)	N1—C15—H15	119.2
O6—Ni1—N1	89.75 (10)	C16—C15—H15	119.2
O5—Ni1—N1	87.97 (9)	C15—C16—C17	119.3 (4)
O3ⁱ—Ni1—N2	94.20 (9)	C15—C16—H16	120.3
O1—Ni1—N2	165.48 (9)	C17—C16—H16	120.4
O6—Ni1—N2	98.04 (9)	C18—C17—C16	119.8 (4)
O5—Ni1—N2	87.46 (9)	C18—C17—H17	120.1
N1—Ni1—N2	75.96 (10)	C16—C17—H17	120.1
O4—C1—O3	124.2 (3)	C17—C18—C19	118.7 (4)
O4—C1—C2	118.9 (3)	C17—C18—H18	120.7
O3—C1—C2	116.9 (3)	C19—C18—H18	120.7
C3—C2—C7	117.8 (3)	N1—C19—C18	121.1 (3)
C3—C2—C1	117.3 (3)	N1—C19—C20	115.7 (3)
C7—C2—C1	124.9 (3)	C18—C19—C20	123.2 (3)
C4—C3—C2	122.3 (4)	N2—C20—C21	121.7 (3)
C4—C3—H3	118.8	N2—C20—C19	115.4 (3)
C2—C3—H3	118.8	C21—C20—C19	122.9 (3)
C5—C4—C3	120.5 (3)	C22—C21—C20	119.2 (4)
C5—C4—H4	119.7	C22—C21—H21	120.4
C3—C4—H4	119.7	C20—C21—H21	120.4
C4—C5—C6	119.4 (3)	C23—C22—C21	119.5 (3)
C4—C5—H5	120.3	C23—C22—H22	120.3
C6—C5—H5	120.3	C21—C22—H22	120.3
C5—C6—C7	120.0 (4)	C22—C23—C24	119.0 (3)
C5—C6—H6	120.0	C22—C23—H23	120.5
C7—C6—H6	120.0	C24—C23—H23	120.5
C2—C7—C6	119.8 (3)	N2—C24—C23	122.5 (3)
C2—C7—C8	122.7 (3)	N2—C24—H24	118.7
C6—C7—C8	116.9 (3)	C23—C24—H24	118.7
C13—C8—C9	116.8 (3)	C15—N1—C19	119.5 (3)
C13—C8—C7	124.4 (3)	C15—N1—Ni1	124.1 (2)
C9—C8—C7	118.8 (3)	C19—N1—Ni1	115.6 (2)
C10—C9—C8	124.3 (3)	C20—N2—C24	118.1 (3)
C10—C9—H9	117.9	C20—N2—Ni1	116.4 (2)
C8—C9—H9	117.8	C24—N2—Ni1	125.4 (2)
C11—C10—C9	118.5 (3)	C14—O1—Ni1	132.81 (19)
C11—C10—H10	120.7	C1—O3—Ni1ⁱⁱ	129.1 (2)
C9—C10—H10	120.8	Ni1—O5—H1W	99 (2)
C10—C11—C12	118.1 (3)	Ni1—O5—H2W	117 (2)
C10—C11—H11	121.0	H1W—O5—H2W	104 (2)
C12—C11—H11	120.9	Ni1—O6—H3W	102 (3)
C13—C12—C11	123.6 (3)	Ni1—O6—H4W	95 (3)
C13—C12—H12	118.2	H3W—O6—H4W	112 (3)
C11—C12—H12	118.2

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1W···Cg1	0.86 (2)	2.91	3.741 (3)	163
O5—H2W···O2ⁱ	0.85 (2)	1.90 (2)	2.740 (3)	169 (3)
O6—H3W···O4ⁱ	0.81 (2)	1.91 (2)	2.676 (4)	158 (4)
O6—H4W···O2	0.82 (2)	1.98 (2)	2.790 (3)	167 (4)

Symmetry code: (i) x−1/2, −y+3/2, −z+2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₄H₈O₄)(C₁₀H₈N₂)(H₂O)₂]
M_r	491.11
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	10.9087 (15), 11.214 (2), 18.129 (3)
V (Å³)	2217.6 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.42 × 0.27 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.699, 0.845
No. of measured, independent and observed [I > 2σ(I)] reflections	11746, 3953, 3351
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 1.00
No. of reflections	3953
No. of parameters	310
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.30
Absolute structure	Flack (1983), 1694 Friedel pairs
Absolute structure parameter	0.042 (16)

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