Aqua­(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)diformato-κ2O,O′;κO-nickel(II) monohydrate

Xia, P.; Lin, J.-L.; Ni, S.-L.

doi:10.1107/S1600536811030558

metal-organic compounds

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Volume 67| Part 9| September 2011| Page m1181

doi:10.1107/S1600536811030558

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Aqua(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)diformato-κ²O,O′;κO-nickel(II) monohydrate

Ping Xia,^a Jian-Li Lin ^b and Sheng-Liang Ni ^a ^*

^aDepartment of Chemistry, Huzhou Teachers College, Huzhou, Zhejiang 313000, People's Republic of China, and ^bCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: shengliangni@163.com

(Received 17 July 2011; accepted 29 July 2011; online 2 August 2011)

The asymmetric unit of the title compound, [Ni(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O, contains a mononuclear complex molecule hydrogen bonded to a lattice water molecule. The Ni^II atom exhibits a distorted octahedral coordination geometry formed by the N atoms from a 2,9-dimethyl-1,10-phenanthroline ligand, two O atoms of a chelating formate anion, one aqua O atom and one O atom of a coordinating formate anion. The molecules are assembled into chains extending along [100] through by O—H⋯O hydrogen bonds. The supramolecular chains are further linked into layers parallel to (011) by weak π–π packing interactions [centroid–centroid separation = 3.768 (2) Å]. The resulting layers are stacked to meet the requirement of close-packing patterns.

Related literature

For general background to supramolecular architectures, see: Moulton & Zaworotko (2001 ); Aakeroy & Seddon (1993 ). For related structures, see: Go et al. (2004 ); Wang et al. (2006); Ni et al. (2011 ).

Experimental

Crystal data

[Ni(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O
M_r = 393.03
Triclinic, $[P \overline 1]$
a = 7.3992 (15) Å
b = 10.373 (2) Å
c = 11.442 (2) Å
α = 82.42 (3)°
β = 81.77 (3)°
γ = 76.10 (3)°
V = 839.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.19 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.750, T_max = 0.821
8265 measured reflections
3785 independent reflections
3214 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.118
S = 1.22
3785 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4ⁱ	0.86	1.85	2.703 (3)	173.3
O5—H52⋯O6ⁱⁱ	0.84	2.03	2.808 (4)	154.2
O6—H61⋯O2ⁱⁱⁱ	0.85	1.98	2.830 (4)	179.3
O6—H62⋯O3^iv	0.85	2.43	3.077 (4)	133.4
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1; (iii) x, y, z-1; (iv) -x+1, -y, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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 global, I. DOI: 10.1107/S1600536811030558/zk2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811030558/zk2016Isup2.hkl

checkCIF report

Comment top

In the past decade, a variety of supramolecular architectures based on non–covalent intermolecular interactions such as hydrogen bonding, van der Walls forces and π–π interactions have been achieved by using transition metal centers and organic ligands due to their possible intriguing structural topologies and potential applications in optics, catalysis, ion exchange, gas storage, and the molecular–based magnetic materials (Aakeroy & Seddon, 1993). Carboxylate ligands have been actively utilized as construction units to obtain lots of supramolecular complexes (Moulton & Zaworotko, 2001). In the paper, we are interested in self–assemblies of Ni^II ions and 2,9'–dimethyl–1,10'–phenanthroline with formic acid, leading to successful preparation of a complex [Ni(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)].H₂O. The asymmetric unit of the title compound consists of one Ni^II ion, one H₂O molecule, one 2,9'–dimethyl–1,10'–phenanthroline molecule, one O,O'–chelated formate anion and another coordinated formate anion, and one lattice H₂O molecule(Fig. 1). It's worth to mention, the tetragonal plane is built up by a pair of bidentate formate anions using carboxyl oxygen atoms (Ni–O1 = 2.148 (3) Å, Ni–O2 = 2.150 (3) Å) and by a neutral 2,9'–dimethyl–1,10'–phenanthroline molecule using nitrogen atoms(Ni–N1 = 2.087 (3) Å, Ni–N2 = 2.076 (3) Å).(Table.1). The four atoms around Ni^II are almost coplanar and show deviations from -0.093 (2) to 0.092 (2) Å with the average plane, the axial positions are occupied by a pair of oxygen originating from H₂O (Ni–O5 = 2.067 (3) Å) and formate anion (Ni–O3 = 2.046 (2) Å), significantly shorter than the Ni–O1 or Ni–O2 bond distance, which are similar to those observed in related complexes with carboxylate complexes(Go et al., 2004; Wang et al., 2006; Ni et al., 2011). The selected bond angles of O1–Ni–O2, N1–Ni–N2, O3–Ni–O5 are 81.5 (1) °, 61.0 (1) °, and 175.9 (1) °, respectively. For two formate anions, the angle (O1–C1–O2, 122.0 (3) °) of chelated formate is smaller than coordinated (O3–C2–O4, 127.6 (3) Å). The 2,9'–dimethyl–1, 10'–phenanthroline ligand are almost coplanar with the mean square deviations 0.0158 Å, the water molecule is not coordinated to Ni atom and the distance between nickel and water oxygen atom of 7.146 (2) Å.

The molecules are assembled into one-dimensional chains extending along the [100] direction through O5–H51···O4^#1, O5–H52···O6^#2, O6–H61···O2^#3 and O6–H61···O3^#4 hydrogen bonds(#1 = x + 1, y, z; #2 = -x + 2, -y, -z + 1; #3 = x, y, z - 1; #4 = -x + 1, -y, -z + 1)(Table.2), the double chains are further linked into two-dimensional layers which parallel to (011) by weak π–π packing interaction(ring centroid separation, 3.768 (2) Å).(Fig. 2). The resulting layers are stacked to meet the requirement of close–packing patterns.

Related literature top

For general background to supramolecular architectures, see: Moulton & Zaworotko (2001); Aakeroy & Seddon (1993). For related structures, see: Go et al. (2004); Wang et al. (2006); Ni et al. (2011).

Experimental top

Dropwise addition of 2.0 ml of 1.0 mol.l^-1 aqueous Na₂CO₃ to a stirred aqueous solation of NiSO₄.7H₂O (0.2876 g, 1.0 mmol) in 5.0 ml H₂O produced a green precipitate, Ni(OH)_2–2x(CO₃)_x.yH₂O, which was centrifuged and washed with water until no SO₄^2- anions were detected in the supernatant. The precipitate was added to a stirred aqueous ethanolic solution of 2,9'–dimethyl–1,10'–phenanthroline in 15 ml EtOH–H₂O (2:1,v/v). And then, 2.0 ml of 1.0 mol.l^-1aqueous formalic acid was dropwise added to above mixture and stirred continuously until dissolved of the green precipitate. The green solution (pH = 3.37) was allowed to stand at room temperature. Slow evaporation during two weeks afforded green block crystals(yield:42%).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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. ORTEP view of the title compound. The dispalcement ellipsoids are drawn at 45% probability level.
	Fig. 2. two-dimensional layer structure link through hydrogen bonds and π–π packing interactions of the title compound

Aqua(2,9'-dimethyl-1,10'-phenanthroline-κ²N,N')diformato- κ²O,O';κO-nickel(II) monohydrate top

Crystal data top

[Ni(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O	Z = 2
M_r = 393.03	F(000) = 408
Triclinic, P1	D_x = 1.555 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3992 (15) Å	Cell parameters from 25 reflections
b = 10.373 (2) Å	θ = 3.1–27.4°
c = 11.442 (2) Å	µ = 1.19 mm⁻¹
α = 82.42 (3)°	T = 298 K
β = 81.77 (3)°	Block, green
γ = 76.10 (3)°	0.30 × 0.20 × 0.15 mm
V = 839.3 (3) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	3785 independent reflections
Radiation source: fine-focus sealed tube	3214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.4°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
T_min = 0.750, T_max = 0.821	k = −13→13
8265 measured reflections	l = −14→14

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.118	w = 1/[σ²(F_o²) + (0.0328P)² + 1.2744P] where P = (F_o² + 2F_c²)/3
S = 1.22	(Δ/σ)_max = 0.001
3785 reflections	Δρ_max = 0.69 e Å⁻³
226 parameters	Δρ_min = −0.67 e Å⁻³
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (3)

Crystal data top

[Ni(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O	γ = 76.10 (3)°
M_r = 393.03	V = 839.3 (3) Å³
Triclinic, P1	Z = 2
a = 7.3992 (15) Å	Mo Kα radiation
b = 10.373 (2) Å	µ = 1.19 mm⁻¹
c = 11.442 (2) Å	T = 298 K
α = 82.42 (3)°	0.30 × 0.20 × 0.15 mm
β = 81.77 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3785 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3214 reflections with I > 2σ(I)
T_min = 0.750, T_max = 0.821	R_int = 0.025
8265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.22	Δρ_max = 0.69 e Å⁻³
3785 reflections	Δρ_min = −0.67 e Å⁻³
226 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
Ni	0.77473 (5)	0.18268 (4)	0.77154 (3)	0.02776 (13)
O1	0.8178 (4)	−0.0310 (2)	0.7920 (3)	0.0540 (7)
O2	0.7827 (4)	0.0786 (3)	0.9468 (2)	0.0494 (6)
C1	0.8093 (6)	−0.0283 (4)	0.9011 (4)	0.0535 (10)
H1A	0.8232	−0.1082	0.9500	0.064*
O3	0.4915 (3)	0.1977 (2)	0.7917 (2)	0.0395 (5)
O4	0.2105 (3)	0.3030 (3)	0.8671 (2)	0.0485 (6)
C2	0.3833 (5)	0.2772 (4)	0.8554 (3)	0.0418 (8)
H2A	0.4386	0.3228	0.8997	0.050*
O5	1.0628 (3)	0.1559 (2)	0.7442 (2)	0.0378 (5)
H52	1.1256	0.0773	0.7581	0.045*
H51	1.1024	0.2025	0.7876	0.045*
O6	0.6484 (4)	0.0613 (3)	0.1914 (2)	0.0544 (7)
H61	0.6881	0.0662	0.1176	0.065*
H62	0.5887	0.0096	0.2356	0.065*
N1	0.7660 (3)	0.3828 (2)	0.7853 (2)	0.0271 (5)
N2	0.7565 (4)	0.2549 (3)	0.5945 (2)	0.0296 (5)
C3	0.7791 (6)	0.3669 (4)	0.9991 (3)	0.0460 (9)
H3A	0.7739	0.2766	0.9924	0.069*
H3B	0.6727	0.4074	1.0509	0.069*
H3C	0.8922	0.3672	1.0310	0.069*
C4	0.7770 (4)	0.4441 (3)	0.8789 (3)	0.0334 (7)
C5	0.7852 (5)	0.5793 (4)	0.8660 (4)	0.0456 (9)
H5A	0.7951	0.6194	0.9321	0.055*
C6	0.7789 (6)	0.6518 (4)	0.7588 (4)	0.0493 (9)
H6A	0.7825	0.7415	0.7516	0.059*
C7	0.7668 (5)	0.5908 (3)	0.6584 (3)	0.0393 (7)
C8	0.7604 (6)	0.6596 (4)	0.5418 (4)	0.0530 (10)
H8A	0.7629	0.7496	0.5305	0.064*
C9	0.7509 (6)	0.5968 (4)	0.4485 (4)	0.0527 (10)
H9A	0.7458	0.6441	0.3736	0.063*
C10	0.7485 (5)	0.4584 (4)	0.4624 (3)	0.0412 (8)
C11	0.7418 (6)	0.3871 (5)	0.3671 (3)	0.0530 (10)
H11A	0.7382	0.4300	0.2906	0.064*
C12	0.7406 (6)	0.2557 (5)	0.3877 (3)	0.0530 (10)
H12A	0.7360	0.2085	0.3249	0.064*
C13	0.7465 (5)	0.1901 (4)	0.5032 (3)	0.0392 (7)
C14	0.7372 (7)	0.0465 (4)	0.5273 (4)	0.0602 (11)
H14A	0.7439	0.0183	0.6102	0.090*
H14B	0.8404	−0.0066	0.4815	0.090*
H14C	0.6214	0.0358	0.5057	0.090*
C15	0.7550 (4)	0.3872 (3)	0.5750 (3)	0.0306 (6)
C16	0.7622 (4)	0.4551 (3)	0.6761 (3)	0.0301 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni	0.0320 (2)	0.0254 (2)	0.0280 (2)	−0.01022 (15)	−0.00438 (15)	−0.00207 (14)
O1	0.078 (2)	0.0316 (13)	0.0548 (17)	−0.0161 (13)	−0.0093 (14)	−0.0044 (11)
O2	0.0675 (18)	0.0447 (15)	0.0364 (13)	−0.0178 (13)	−0.0080 (12)	0.0058 (11)
C1	0.070 (3)	0.0368 (19)	0.052 (2)	−0.0164 (18)	−0.0105 (19)	0.0139 (17)
O3	0.0273 (11)	0.0512 (14)	0.0448 (13)	−0.0162 (10)	−0.0022 (10)	−0.0107 (11)
O4	0.0317 (13)	0.0651 (17)	0.0524 (15)	−0.0129 (12)	−0.0027 (11)	−0.0177 (13)
C2	0.0361 (18)	0.056 (2)	0.0394 (18)	−0.0179 (16)	−0.0018 (14)	−0.0144 (16)
O5	0.0293 (11)	0.0398 (12)	0.0462 (13)	−0.0070 (9)	−0.0104 (10)	−0.0054 (10)
O6	0.0642 (18)	0.0550 (16)	0.0460 (15)	−0.0148 (14)	−0.0076 (13)	−0.0080 (12)
N1	0.0247 (12)	0.0272 (12)	0.0303 (12)	−0.0059 (10)	−0.0023 (9)	−0.0072 (9)
N2	0.0316 (13)	0.0338 (13)	0.0248 (12)	−0.0104 (11)	−0.0033 (10)	−0.0028 (10)
C3	0.052 (2)	0.061 (2)	0.0322 (17)	−0.0201 (18)	−0.0079 (15)	−0.0130 (16)
C4	0.0290 (15)	0.0397 (17)	0.0350 (16)	−0.0114 (13)	0.0011 (12)	−0.0147 (13)
C5	0.045 (2)	0.045 (2)	0.054 (2)	−0.0166 (16)	0.0011 (16)	−0.0251 (17)
C6	0.054 (2)	0.0294 (17)	0.067 (3)	−0.0139 (16)	0.0035 (19)	−0.0152 (16)
C7	0.0356 (17)	0.0284 (16)	0.053 (2)	−0.0085 (13)	−0.0034 (15)	−0.0005 (14)
C8	0.057 (2)	0.0317 (18)	0.066 (3)	−0.0117 (17)	−0.005 (2)	0.0130 (17)
C9	0.056 (2)	0.052 (2)	0.045 (2)	−0.0155 (19)	−0.0094 (18)	0.0235 (18)
C10	0.0361 (18)	0.050 (2)	0.0353 (17)	−0.0103 (15)	−0.0067 (14)	0.0071 (15)
C11	0.057 (2)	0.075 (3)	0.0253 (17)	−0.014 (2)	−0.0086 (16)	0.0037 (17)
C12	0.062 (3)	0.074 (3)	0.0280 (17)	−0.021 (2)	−0.0083 (16)	−0.0125 (17)
C13	0.0382 (18)	0.0484 (19)	0.0346 (17)	−0.0101 (15)	−0.0039 (13)	−0.0165 (14)
C14	0.085 (3)	0.057 (2)	0.052 (2)	−0.030 (2)	−0.009 (2)	−0.0245 (19)
C15	0.0275 (15)	0.0337 (15)	0.0304 (15)	−0.0087 (12)	−0.0043 (12)	0.0016 (12)
C16	0.0304 (15)	0.0274 (14)	0.0335 (15)	−0.0106 (12)	−0.0021 (12)	−0.0006 (11)

Geometric parameters (Å, º) top

Ni—O3	2.046 (2)	C3—H3C	0.9600
Ni—O5	2.066 (2)	C4—C5	1.405 (5)
Ni—N2	2.076 (2)	C5—C6	1.352 (6)
Ni—N1	2.087 (2)	C5—H5A	0.9300
Ni—O1	2.148 (3)	C6—C7	1.406 (5)
Ni—O2	2.150 (2)	C6—H6A	0.9300
Ni—C1	2.457 (4)	C7—C16	1.403 (4)
O1—C1	1.244 (5)	C7—C8	1.429 (5)
O2—C1	1.249 (5)	C8—C9	1.341 (6)
C1—H1A	0.9300	C8—H8A	0.9300
O3—C2	1.235 (4)	C9—C10	1.428 (5)
O4—C2	1.233 (4)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C15	1.399 (4)
O5—H52	0.8426	C10—C11	1.408 (5)
O5—H51	0.8597	C11—C12	1.354 (6)
O6—H61	0.8524	C11—H11A	0.9300
O6—H62	0.8469	C12—C13	1.406 (5)
N1—C4	1.337 (4)	C12—H12A	0.9300
N1—C16	1.370 (4)	C13—C14	1.495 (5)
N2—C13	1.334 (4)	C14—H14A	0.9600
N2—C15	1.359 (4)	C14—H14B	0.9600
C3—C4	1.497 (5)	C14—H14C	0.9600
C3—H3A	0.9600	C15—C16	1.444 (4)
C3—H3B	0.9600

O3—Ni—O5	175.85 (9)	C4—C3—H3C	109.5
O3—Ni—N2	88.19 (10)	H3A—C3—H3C	109.5
O5—Ni—N2	90.52 (10)	H3B—C3—H3C	109.5
O3—Ni—N1	97.19 (10)	N1—C4—C5	121.0 (3)
O5—Ni—N1	86.51 (10)	N1—C4—C3	119.0 (3)
N2—Ni—N1	81.48 (10)	C5—C4—C3	119.9 (3)
O3—Ni—O1	89.42 (11)	C6—C5—C4	121.0 (3)
O5—Ni—O1	87.32 (11)	C6—C5—H5A	119.5
N2—Ni—O1	110.07 (11)	C4—C5—H5A	119.5
N1—Ni—O1	166.96 (10)	C5—C6—C7	119.6 (3)
O3—Ni—O2	88.37 (11)	C5—C6—H6A	120.2
O5—Ni—O2	92.29 (11)	C7—C6—H6A	120.2
N2—Ni—O2	170.43 (10)	C16—C7—C6	117.0 (3)
N1—Ni—O2	107.82 (10)	C16—C7—C8	119.6 (3)
O1—Ni—O2	60.97 (11)	C6—C7—C8	123.4 (3)
O3—Ni—C1	88.83 (13)	C9—C8—C7	121.2 (3)
O5—Ni—C1	89.66 (13)	C9—C8—H8A	119.4
N2—Ni—C1	140.41 (13)	C7—C8—H8A	119.4
N1—Ni—C1	138.01 (12)	C8—C9—C10	120.9 (3)
O1—Ni—C1	30.42 (12)	C8—C9—H9A	119.6
O2—Ni—C1	30.54 (12)	C10—C9—H9A	119.6
C1—O1—Ni	88.6 (2)	C15—C10—C11	117.1 (3)
C1—O2—Ni	88.4 (2)	C15—C10—C9	119.7 (3)
O1—C1—O2	122.0 (3)	C11—C10—C9	123.2 (3)
O1—C1—Ni	60.93 (19)	C12—C11—C10	119.6 (3)
O2—C1—Ni	61.03 (18)	C12—C11—H11A	120.2
O1—C1—H1A	119.0	C10—C11—H11A	120.2
O2—C1—H1A	119.0	C11—C12—C13	120.5 (3)
Ni—C1—H1A	179.7	C11—C12—H12A	119.8
C2—O3—Ni	121.6 (2)	C13—C12—H12A	119.8
O4—C2—O3	127.6 (3)	N2—C13—C12	121.0 (3)
O4—C2—H2A	116.2	N2—C13—C14	118.2 (3)
O3—C2—H2A	116.2	C12—C13—C14	120.8 (3)
Ni—O5—H52	116.4	C13—C14—H14A	109.5
Ni—O5—H51	111.9	C13—C14—H14B	109.5
H52—O5—H51	104.9	H14A—C14—H14B	109.5
H61—O6—H62	132.8	C13—C14—H14C	109.5
C4—N1—C16	118.4 (3)	H14A—C14—H14C	109.5
C4—N1—Ni	130.5 (2)	H14B—C14—H14C	109.5
C16—N1—Ni	110.88 (19)	N2—C15—C10	122.9 (3)
C13—N2—C15	118.9 (3)	N2—C15—C16	117.6 (3)
C13—N2—Ni	129.2 (2)	C10—C15—C16	119.5 (3)
C15—N2—Ni	111.95 (19)	N1—C16—C7	123.0 (3)
C4—C3—H3A	109.5	N1—C16—C15	118.0 (3)
C4—C3—H3B	109.5	C7—C16—C15	119.0 (3)
H3A—C3—H3B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ⁱ	0.86	1.85	2.703 (3)	173.3
O5—H52···O6ⁱⁱ	0.84	2.03	2.808 (4)	154.2
O6—H61···O2ⁱⁱⁱ	0.85	1.98	2.830 (4)	179.3
O6—H62···O3^iv	0.85	2.43	3.077 (4)	133.4

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

Experimental details

Crystal data
Chemical formula	[Ni(HCO₂)₂(C₁₄H₁₂N₂)(H₂O)]·H₂O
M_r	393.03
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.3992 (15), 10.373 (2), 11.442 (2)
α, β, γ (°)	82.42 (3), 81.77 (3), 76.10 (3)
V (Å³)	839.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.19
Crystal size (mm)	0.30 × 0.20 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.750, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	8265, 3785, 3214
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.118, 1.22
No. of reflections	3785
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.67

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), 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
O5—H51···O4ⁱ	0.86	1.85	2.703 (3)	173.3
O5—H52···O6ⁱⁱ	0.84	2.03	2.808 (4)	154.2
O6—H61···O2ⁱⁱⁱ	0.85	1.98	2.830 (4)	179.3
O6—H62···O3^iv	0.85	2.43	3.077 (4)	133.4

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

Acknowledgements

This work was supported by the Huzhou Municipal Foundation of Science and Technology (2011 GG15) and the Foundation of the Education Department of Zhejiang Province (ZC200805662).

References

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