cis-Aqua-bis(2,4-dichloro-6-formyl-phenolato-κO,O')(N,N-dimethyl-formamide-κO)nickel(II).

In the title compound, [Ni(C(7)H(3)Cl(2)O(2))(2)(C(3)H(7)NO)(H(2)O)], the Ni(II) ion is coordinated by four O atoms from two bidentate 2,4-dichloro-6-formyl-phenolate ligands, one O atom from a water ligand and one O atom from a dimethyl-formamide ligand in a slightly distorted octa-hedral environment. In the crystal structure, centrosymmetric dimers are formed though O-H⋯O and O-H⋯Cl hydrogen bonds; π-π stacking inter-actions, with a centroid-centroid distance of 3.796 (2) Å, are also found.

Related literature

For related literature, see: Cohen et al. (1964 ▶); Desiraju (1989 ▶); Mathews & Manohar (1991 ▶); Zaman et al. (2004 ▶); Zhang et al. (2007 ▶); Zordan et al. (2005 ▶).

Experimental

Crystal data

[Ni(C7H3Cl2O2)2(C3H7NO)(H2O)]

M = 529.81

Monoclinic,

a = 10.404 (2) Å

b = 9.6130 (19) Å

c = 22.161 (4) Å

β = 92.44 (3)°

V = 2214.4 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.39 mm−1

T = 293 (2) K

0.48 × 0.40 × 0.35 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.555, T max = 0.642

10765 measured reflections

3969 independent reflections

3010 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.07

3969 reflections

266 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 datablocks global, I. DOI: 10.1107/S1600536808022939/lh2644sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022939/lh2644Isup2.hkl

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

[Ni(C7H3Cl2O2)2(C3H7N1O1)(H2O1)]	F000 = 1072
Mr = 529.81	Dx = 1.589 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3969 reflections
a = 10.404 (2) Å	θ = 1.8–25.2º
b = 9.6130 (19) Å	µ = 1.39 mm−1
c = 22.161 (4) Å	T = 293 (2) K
β = 92.44 (3)º	Block, green
V = 2214.4 (8) Å3	0.48 × 0.40 × 0.35 mm
Z = 4

Bruker SMART CCD diffractometer	3969 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.036
Detector resolution: 0 pixels mm-1	θmax = 25.2º
T = 293(2) K	θmin = 1.8º
ω scans	h = −12→12
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.555, Tmax = 0.642	l = −23→26
10765 measured reflections

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0455P)2 + 2.189P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3969 reflections	Δρmax = 0.59 e Å−3
266 parameters	Δρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Ni1	0.20449 (4)	0.95403 (5)	0.46317 (2)	0.03298 (15)
Cl3	−0.19959 (10)	0.74563 (12)	0.37793 (5)	0.0551 (3)
Cl1	0.04788 (11)	0.62415 (13)	0.61561 (5)	0.0620 (3)
Cl4	−0.17775 (12)	1.10954 (17)	0.18744 (5)	0.0754 (4)
Cl2	0.48052 (13)	0.70149 (19)	0.75310 (6)	0.0915 (5)
O2	0.3577 (2)	1.0446 (3)	0.51032 (11)	0.0395 (6)
O1	0.1544 (2)	0.8520 (3)	0.53947 (10)	0.0363 (6)
O4	0.2662 (2)	1.0551 (3)	0.38720 (11)	0.0439 (7)
O6	0.1041 (2)	1.1430 (3)	0.48293 (13)	0.0384 (6)
H6A	0.0272	1.1332	0.4743	0.058*
O3	0.0510 (2)	0.8740 (3)	0.41437 (10)	0.0374 (6)
O5	0.3235 (2)	0.7792 (3)	0.44247 (12)	0.0437 (7)
C1	0.2302 (3)	0.8212 (4)	0.58538 (15)	0.0335 (8)
C7	0.4025 (3)	1.0013 (4)	0.55949 (17)	0.0393 (9)
H7A	0.4775	1.0444	0.5742	0.047*
C8	0.0074 (3)	0.9226 (4)	0.36312 (16)	0.0335 (8)
C9	−0.1159 (3)	0.8770 (4)	0.33844 (16)	0.0381 (9)
C5	0.4263 (4)	0.8523 (5)	0.64989 (17)	0.0485 (11)
H5A	0.5037	0.8981	0.6584	0.058*
C11	−0.1049 (4)	1.0351 (5)	0.25254 (17)	0.0491 (11)
C4	0.3865 (4)	0.7480 (5)	0.68905 (18)	0.0536 (12)
C13	0.0725 (4)	1.0237 (4)	0.32556 (16)	0.0405 (9)
C12	0.0161 (4)	1.0781 (5)	0.27125 (17)	0.0491 (11)
H12A	0.0604	1.1422	0.2486	0.059*
C6	0.3515 (3)	0.8893 (4)	0.59776 (16)	0.0363 (9)
C3	0.2688 (4)	0.6781 (5)	0.67818 (19)	0.0531 (11)
H3A	0.2423	0.6093	0.7044	0.064*
C14	0.2000 (4)	1.0767 (4)	0.34105 (18)	0.0456 (10)
H14A	0.2360	1.1341	0.3125	0.055*
C10	−0.1696 (4)	0.9316 (4)	0.28593 (17)	0.0450 (10)
H10A	−0.2501	0.9005	0.2719	0.054*
C2	0.1946 (4)	0.7137 (4)	0.62829 (18)	0.0424 (9)
N1	0.3665 (4)	0.5364 (4)	0.43658 (16)	0.0520 (9)
C15	0.2951 (4)	0.6490 (5)	0.45053 (17)	0.0454 (10)
H15A	0.2169	0.6310	0.4678	0.054*
C16	0.4864 (5)	0.5594 (6)	0.4064 (3)	0.0785 (16)
H16A	0.5039	0.6574	0.4049	0.118*
H16B	0.4787	0.5230	0.3661	0.118*
H16C	0.5554	0.5131	0.4284	0.118*
C17	0.3215 (7)	0.3854 (5)	0.4433 (3)	0.102 (2)
H17A	0.2417	0.3840	0.4635	0.152*
H17B	0.3852	0.3339	0.4666	0.152*
H17C	0.3093	0.3440	0.4041	0.152*
H6B	0.098 (4)	1.144 (5)	0.5204 (19)	0.053 (14)*

	U11	U22	U33	U12	U13	U23
Ni1	0.0240 (2)	0.0404 (3)	0.0343 (3)	−0.0019 (2)	−0.00076 (18)	0.0032 (2)
Cl3	0.0426 (6)	0.0615 (7)	0.0608 (7)	−0.0183 (5)	−0.0015 (5)	−0.0011 (5)
Cl1	0.0498 (6)	0.0627 (8)	0.0729 (8)	−0.0140 (6)	−0.0032 (5)	0.0246 (6)
Cl4	0.0634 (8)	0.1139 (12)	0.0473 (7)	0.0148 (7)	−0.0164 (6)	0.0139 (7)
Cl2	0.0638 (8)	0.1517 (15)	0.0571 (8)	0.0273 (9)	−0.0192 (6)	0.0263 (8)
O2	0.0269 (13)	0.0485 (16)	0.0427 (15)	−0.0026 (12)	−0.0017 (11)	0.0023 (12)
O1	0.0250 (12)	0.0498 (16)	0.0338 (13)	−0.0039 (11)	−0.0017 (10)	0.0079 (12)
O4	0.0331 (14)	0.0597 (18)	0.0389 (15)	−0.0096 (13)	0.0006 (12)	0.0086 (13)
O6	0.0254 (13)	0.0477 (17)	0.0420 (16)	0.0006 (11)	0.0006 (11)	0.0018 (13)
O3	0.0291 (13)	0.0466 (16)	0.0362 (14)	−0.0065 (11)	−0.0026 (11)	0.0037 (12)
O5	0.0376 (15)	0.0380 (16)	0.0558 (17)	0.0015 (12)	0.0049 (12)	−0.0017 (13)
C1	0.0301 (19)	0.038 (2)	0.0329 (19)	0.0057 (16)	0.0028 (15)	−0.0011 (16)
C7	0.0231 (17)	0.049 (2)	0.046 (2)	−0.0035 (17)	−0.0017 (16)	−0.0043 (19)
C8	0.0279 (18)	0.038 (2)	0.034 (2)	0.0025 (16)	0.0010 (15)	−0.0049 (16)
C9	0.033 (2)	0.041 (2)	0.040 (2)	−0.0006 (17)	0.0021 (16)	−0.0042 (17)
C5	0.031 (2)	0.071 (3)	0.043 (2)	0.010 (2)	−0.0048 (17)	−0.008 (2)
C11	0.042 (2)	0.071 (3)	0.033 (2)	0.010 (2)	−0.0061 (17)	−0.002 (2)
C4	0.042 (2)	0.082 (3)	0.036 (2)	0.018 (2)	−0.0031 (18)	0.007 (2)
C13	0.033 (2)	0.054 (3)	0.035 (2)	−0.0012 (18)	0.0016 (16)	−0.0016 (18)
C12	0.049 (2)	0.059 (3)	0.040 (2)	−0.001 (2)	0.0009 (19)	0.008 (2)
C6	0.0258 (18)	0.047 (2)	0.036 (2)	0.0043 (16)	0.0015 (15)	−0.0056 (17)
C3	0.045 (2)	0.067 (3)	0.047 (2)	0.012 (2)	0.004 (2)	0.016 (2)
C14	0.043 (2)	0.057 (3)	0.038 (2)	−0.011 (2)	0.0053 (18)	0.0128 (19)
C10	0.031 (2)	0.060 (3)	0.044 (2)	0.0008 (19)	−0.0034 (17)	−0.015 (2)
C2	0.038 (2)	0.044 (2)	0.045 (2)	0.0038 (18)	0.0032 (17)	0.0064 (19)
N1	0.056 (2)	0.041 (2)	0.059 (2)	−0.0003 (17)	−0.0052 (18)	−0.0027 (17)
C15	0.040 (2)	0.053 (3)	0.043 (2)	−0.010 (2)	−0.0007 (18)	−0.003 (2)
C16	0.066 (3)	0.075 (4)	0.096 (4)	0.020 (3)	0.015 (3)	−0.009 (3)
C17	0.124 (6)	0.037 (3)	0.142 (6)	−0.015 (3)	−0.008 (5)	0.001 (3)

Ni1—O3	2.041 (2)	C5—C4	1.400 (6)
Ni1—O1	2.041 (2)	C5—C6	1.411 (5)
Ni1—O2	2.061 (3)	C5—H5A	0.9300
Ni1—O4	2.070 (3)	C11—C12	1.372 (6)
Ni1—O5	2.148 (3)	C11—C10	1.426 (6)
Ni1—O6	2.150 (3)	C4—C3	1.408 (6)
Cl3—C9	1.784 (4)	C13—C12	1.416 (5)
Cl1—C2	1.764 (4)	C13—C14	1.448 (5)
Cl4—C11	1.754 (4)	C12—H12A	0.9300
Cl2—C4	1.748 (4)	C3—C2	1.365 (5)
O2—C7	1.239 (4)	C3—H3A	0.9300
O1—C1	1.295 (4)	C14—H14A	0.9300
O4—C14	1.226 (4)	C10—H10A	0.9300
O6—H6A	0.8200	N1—C15	1.356 (5)
O6—H6B	0.83 (4)	N1—C16	1.456 (6)
O3—C8	1.292 (4)	N1—C17	1.534 (6)
O5—C15	1.301 (5)	C15—H15A	0.9300
C1—C6	1.437 (5)	C16—H16A	0.9600
C1—C2	1.463 (5)	C16—H16B	0.9600
C7—C6	1.483 (5)	C16—H16C	0.9600
C7—H7A	0.9300	C17—H17A	0.9600
C8—C9	1.441 (5)	C17—H17B	0.9600
C8—C13	1.465 (5)	C17—H17C	0.9600
C9—C10	1.374 (5)
O3—Ni1—O1	92.08 (10)	C5—C4—Cl2	121.1 (4)
O3—Ni1—O2	177.03 (10)	C3—C4—Cl2	118.0 (3)
O1—Ni1—O2	90.12 (10)	C12—C13—C14	114.5 (4)
O3—Ni1—O4	90.51 (10)	C12—C13—C8	122.9 (3)
O1—Ni1—O4	176.71 (10)	C14—C13—C8	122.7 (3)
O2—Ni1—O4	87.36 (10)	C11—C12—C13	119.2 (4)
O3—Ni1—O5	92.13 (10)	C11—C12—H12A	120.4
O1—Ni1—O5	88.33 (10)	C13—C12—H12A	120.4
O2—Ni1—O5	89.92 (10)	C5—C6—C1	119.4 (4)
O4—Ni1—O5	89.55 (11)	C5—C6—C7	116.9 (3)
O3—Ni1—O6	92.88 (10)	C1—C6—C7	123.7 (3)
O1—Ni1—O6	95.38 (10)	C2—C3—C4	118.5 (4)
O2—Ni1—O6	84.93 (10)	C2—C3—H3A	120.8
O4—Ni1—O6	86.51 (11)	C4—C3—H3A	120.8
O5—Ni1—O6	173.65 (10)	O4—C14—C13	127.9 (4)
C7—O2—Ni1	123.9 (2)	O4—C14—H14A	116.0
C1—O1—Ni1	126.3 (2)	C13—C14—H14A	116.0
C14—O4—Ni1	125.1 (2)	C9—C10—C11	121.5 (4)
Ni1—O6—H6A	109.5	C9—C10—H10A	119.3
Ni1—O6—H6B	106 (3)	C11—C10—H10A	119.3
H6A—O6—H6B	96.5	C3—C2—C1	123.6 (4)
C8—O3—Ni1	124.5 (2)	C3—C2—Cl1	117.6 (3)
C15—O5—Ni1	126.0 (2)	C1—C2—Cl1	118.9 (3)
O1—C1—C6	123.1 (3)	C15—N1—C16	118.1 (4)
O1—C1—C2	120.6 (3)	C15—N1—C17	124.0 (4)
C6—C1—C2	116.3 (3)	C16—N1—C17	117.4 (4)
O2—C7—C6	128.0 (3)	O5—C15—N1	127.4 (4)
O2—C7—H7A	116.0	O5—C15—H15A	116.3
C6—C7—H7A	116.0	N1—C15—H15A	116.3
O3—C8—C9	119.8 (3)	N1—C16—H16A	109.5
O3—C8—C13	125.9 (3)	N1—C16—H16B	109.5
C9—C8—C13	114.4 (3)	H16A—C16—H16B	109.5
C10—C9—C8	121.9 (4)	N1—C16—H16C	109.5
C10—C9—Cl3	119.8 (3)	H16A—C16—H16C	109.5
C8—C9—Cl3	118.3 (3)	H16B—C16—H16C	109.5
C4—C5—C6	121.4 (4)	N1—C17—H17A	109.5
C4—C5—H5A	119.3	N1—C17—H17B	109.5
C6—C5—H5A	119.3	H17A—C17—H17B	109.5
C12—C11—C10	120.1 (4)	N1—C17—H17C	109.5
C12—C11—Cl4	119.0 (3)	H17A—C17—H17C	109.5
C10—C11—Cl4	120.9 (3)	H17B—C17—H17C	109.5
C5—C4—C3	120.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1i	0.82	1.91	2.714 (3)	168
O6—H6B···O3i	0.83 (4)	2.17 (4)	2.850 (4)	139 (4)
O6—H6B···Cl3i	0.84 (4)	2.67 (4)	3.374 (3)	143 (4)

Table 1

Selected bond lengths (Å)

Ni1—O3	2.041 (2)
Ni1—O1	2.041 (2)
Ni1—O2	2.061 (3)
Ni1—O4	2.070 (3)
Ni1—O5	2.148 (3)
Ni1—O6	2.150 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1i	0.82	1.91	2.714 (3)	168
O6—H6B⋯O3i	0.83 (4)	2.17 (4)	2.850 (4)	139 (4)
O6—H6B⋯Cl3i	0.84 (4)	2.67 (4)	3.374 (3)	143 (4)

Symmetry code: (i) .