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

The asymmetric unit of the title compound, [Ni(HCO(2))(2)(C(14)H(12)N(2))(H(2)O)]·H(2)O, contains a mononuclear complex mol-ecule hydrogen bonded to a lattice water mol-ecule. The Ni(II) atom exhibits a distorted octa-hedral 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 mol-ecules are assembled into chains extending along [100] through by O-H⋯O hydrogen bonds. The supra-molecular chains are further linked into layers parallel to (011) by weak π-π packing inter-actions [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 = 393.03

Triclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.118

S = 1.22

3785 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.67 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030558/zk2016sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(HCO2)2(C14H12N2)(H2O)]·H2O	Z = 2
Mr = 393.03	F(000) = 408
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0328P)2 + 1.2744P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max = 0.001
3785 reflections	Δρmax = 0.69 e Å−3
226 parameters	Δρmin = −0.67 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0015 (3)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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

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···O3iv	0.85	2.43	3.077 (4)	133.4

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⋯O3iv	0.85	2.43	3.077 (4)	133.4

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .