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Acta Cryst. (2007). E63, m3002    [ doi:10.1107/S1600536807056681 ]

Aqua(dimethylglyoxime-[kappa]2N,N')(3,5-dinitro-2-oxidobenzoato-[kappa]2O,O')nickel(II)

Y.-Q. Liu

Abstract top

In the mononuclear title complex, [Ni(C7H2N2O7)(C4H8N2O2)(H2O)], the nickel(II) ion is five-coordinated in a distorted square-pyramidal geometry by two N atoms from a dimethylglyoxime molecule, two O atoms from a 2-oxido-3,5-dinitrobenzoate anion and one O atom from a water molecule. Strong hydrogen bonds connect discrete adjacent molecules, forming a ribbon parallel to the b axis.

Comment top

The title complex, [NiC~11Ñ~4~ O~10~H~12~], is a mononuclear nickel(II) compound. The nickel(II) ion is five-coordinated in a distorted pyramidal geometry by two N atoms from one Dimethylglyoxime molecule, two O atoms from one 2-hydroxy-3,5-dinitrobenzoic acid molecule and one O atom from a water molecule (Fig. 1). The water molecule appears to be weakly coordinated to the Ni atom with a rather long Ni—O bond length of 2.365 (1) Å. The Ni atom is located slightly above the basal N3, N4, O6, O7 square plane by 0.0988 (8) Å

Strong hydrogen bonds connect discrete adjacent molecule building a ribbonn parallel to the b axis (Table 1).

Related literature top

Please add any relevant related literature

Experimental top

A mixture of Dimethylglyoxime(0.116 g,0.001 mol), 2-hydroxy-3,5-dinitrobenzoic acid(0.228 g,0.001 mol) and Ni(NO3)2.6H2O (0.290 g, 0.001 mol) in the More ratio of 1:1:1 was added to 15 ml me thanol, The mixture was heated at 408 K or so for two days in a closed steel tomb with a linner, crystal was obtained after it cooled down untouched in the air.

Refinement top

All H atoms attached to C atoms and hydroxyl O atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl) and O—H = 0.82Å with Uiso(H) = 1.2Ueq(Caromatic or Ohydroxyl). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O—H= 0.82 (1)Å and H···H= 1.35 (2) Å) with Uiso(H) = 1.5Ueq(O). In the last stage of refinement, they were treated as riding on the O atom.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular view of compound (I) showing 30% probability displacement ellipsoids and the atom numbering scheme. H atoms are shown as small spheres of arbitrary radii.
Aqua(dimethylglyoxime-κ2N,N')(3,5-dinitro-2-oxidobenzoato- κ2O,O')nickel(II) top
Crystal data top
[Ni(C7H2N2O7)(C4H8N2O2)(H2O)]F(000) = 856.0
Mr = 418.94Dx = 1.804 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7541 reflections
a = 12.476 (2) Åθ = 0.9–28.3°
b = 7.0786 (14) ŵ = 1.32 mm−1
c = 17.929 (4) ÅT = 293 K
β = 103.014 (3)°Block, blue
V = 1542.7 (5) Å30.28 × 0.26 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		2426 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
graphiteθmax = 25.5°, θmin = 2.3°
φ and ω scansh = −14→15
9276 measured reflectionsk = −8→8
2824 independent reflectionsl = −21→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2949P]
where P = (Fo2 + 2Fc2)/3
2824 reflections(Δ/σ)max = 0.003
239 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.26 e Å−3
Crystal data top
[Ni(C7H2N2O7)(C4H8N2O2)(H2O)]V = 1542.7 (5) Å3
Mr = 418.94Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.476 (2) ŵ = 1.32 mm−1
b = 7.0786 (14) ÅT = 293 K
c = 17.929 (4) Å0.28 × 0.26 × 0.22 mm
β = 103.014 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2426 reflections with I > 2σ(I)
9276 measured reflectionsRint = 0.019
2824 independent reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.073Δρmax = 0.20 e Å−3
S = 1.07Δρmin = −0.26 e Å−3
2824 reflectionsAbsolute structure: ?
239 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
C10.38531 (16)0.8249 (3)−0.15675 (10)0.0431 (4)
C20.29061 (16)0.8484 (3)−0.12964 (11)0.0429 (4)
H20.24940.9584−0.14110.051*
C30.25681 (15)0.7100 (3)−0.08576 (10)0.0389 (4)
C40.31731 (15)0.5365 (3)−0.07013 (10)0.0377 (4)
C50.41420 (15)0.5225 (3)−0.09925 (10)0.0379 (4)
C60.44881 (16)0.6656 (3)−0.14101 (10)0.0410 (4)
H60.51370.6539−0.15800.049*
C70.15838 (16)0.7567 (3)−0.05465 (11)0.0434 (4)
C80.2461 (2)−0.0792 (3)0.17163 (15)0.0625 (6)
H8A0.2909−0.14480.14290.094*
H8B0.1793−0.14850.16920.094*
H8C0.2855−0.06810.22400.094*
C90.21937 (16)0.1128 (3)0.13860 (11)0.0441 (5)
C100.1053 (2)0.2006 (4)0.23813 (14)0.0690 (7)
H10A0.08940.31660.26120.104*
H10B0.16100.13250.27360.104*
H10C0.03970.12530.22500.104*
C110.14518 (16)0.2430 (3)0.16752 (11)0.0461 (5)
Ni10.19075 (2)0.41717 (3)0.035803 (14)0.04002 (10)
N10.41838 (17)0.9713 (3)−0.20418 (10)0.0561 (5)
N20.48544 (14)0.3559 (2)−0.08555 (9)0.0455 (4)
N30.25549 (13)0.1823 (2)0.08265 (9)0.0438 (4)
N40.11866 (14)0.3919 (2)0.12644 (10)0.0460 (4)
O10.50896 (16)0.9592 (3)−0.21874 (10)0.0769 (5)
O20.35279 (17)1.0994 (3)−0.22726 (12)0.0866 (6)
O30.57504 (13)0.3662 (3)−0.10271 (11)0.0724 (5)
O40.45619 (13)0.2136 (2)−0.05635 (10)0.0664 (5)
O50.10174 (13)0.89514 (19)−0.08015 (10)0.0573 (4)
O60.13486 (12)0.6563 (2)−0.00039 (9)0.0524 (4)
O70.28663 (13)0.39915 (19)−0.03220 (9)0.0517 (4)
O80.32368 (13)0.0709 (2)0.05091 (9)0.0546 (4)
H80.34130.12810.01570.082*
O90.05069 (15)0.5146 (2)0.15476 (9)0.0638 (4)
H90.02650.59490.12240.096*
O100.04723 (11)0.24631 (18)−0.04489 (8)0.0496 (3)
H10D0.06600.1377−0.05480.074*
H10E−0.00770.2383−0.02610.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0520 (12)0.0435 (11)0.0355 (9)−0.0072 (9)0.0136 (8)0.0006 (8)
C20.0471 (11)0.0367 (10)0.0453 (10)0.0010 (8)0.0112 (9)0.0015 (8)
C30.0413 (10)0.0338 (9)0.0437 (10)0.0015 (8)0.0137 (8)−0.0008 (7)
C40.0418 (11)0.0338 (9)0.0399 (9)0.0002 (8)0.0144 (8)−0.0021 (7)
C50.0396 (10)0.0376 (9)0.0373 (9)0.0016 (8)0.0108 (8)−0.0057 (8)
C60.0418 (11)0.0480 (11)0.0363 (9)−0.0042 (9)0.0155 (8)−0.0067 (8)
C70.0452 (11)0.0310 (9)0.0572 (12)0.0029 (8)0.0178 (9)−0.0011 (8)
C80.0626 (15)0.0570 (14)0.0707 (15)0.0121 (11)0.0208 (12)0.0219 (11)
C90.0389 (11)0.0460 (11)0.0468 (11)0.0001 (8)0.0087 (9)0.0061 (8)
C100.0776 (17)0.0758 (17)0.0639 (14)0.0064 (13)0.0372 (13)0.0187 (12)
C110.0435 (11)0.0496 (11)0.0480 (11)0.0010 (9)0.0163 (9)0.0065 (9)
Ni10.04354 (17)0.03448 (15)0.04867 (16)0.00837 (10)0.02439 (12)0.00723 (10)
N10.0639 (13)0.0591 (12)0.0465 (10)−0.0081 (10)0.0147 (9)0.0104 (8)
N20.0438 (10)0.0474 (9)0.0486 (9)0.0070 (8)0.0171 (8)−0.0047 (7)
N30.0400 (9)0.0443 (9)0.0497 (9)0.0077 (7)0.0159 (7)0.0035 (7)
N40.0463 (10)0.0469 (10)0.0503 (9)0.0057 (7)0.0223 (8)0.0013 (7)
O10.0749 (12)0.0903 (13)0.0777 (11)−0.0063 (10)0.0429 (10)0.0231 (10)
O20.0819 (13)0.0832 (14)0.0964 (14)0.0058 (10)0.0239 (11)0.0487 (11)
O30.0478 (10)0.0778 (11)0.1014 (13)0.0172 (8)0.0373 (9)0.0104 (10)
O40.0708 (11)0.0463 (9)0.0928 (12)0.0153 (8)0.0411 (9)0.0107 (8)
O50.0529 (9)0.0391 (8)0.0841 (11)0.0139 (6)0.0245 (8)0.0084 (7)
O60.0531 (9)0.0430 (8)0.0719 (9)0.0112 (7)0.0366 (8)0.0088 (7)
O70.0581 (9)0.0377 (8)0.0708 (10)0.0111 (6)0.0387 (8)0.0115 (6)
O80.0564 (9)0.0518 (9)0.0622 (9)0.0179 (7)0.0271 (7)0.0063 (7)
O90.0776 (11)0.0594 (10)0.0662 (10)0.0232 (9)0.0413 (9)0.0076 (8)
O100.0461 (8)0.0407 (7)0.0676 (9)0.0087 (6)0.0245 (7)0.0004 (7)
Geometric parameters (Å, °) top
C1—C61.370 (3)C10—C111.492 (3)
C1—C21.385 (3)C10—H10A0.9600
C1—N11.458 (3)C10—H10B0.9600
C2—C31.380 (3)C10—H10C0.9600
C2—H20.9300C11—N41.286 (3)
C3—C41.436 (3)Ni1—O61.8889 (14)
C3—C71.495 (3)Ni1—O71.8949 (14)
C4—O71.293 (2)Ni1—N31.9538 (16)
C4—C51.424 (3)Ni1—N42.0347 (17)
C5—C61.385 (3)Ni1—O102.3654 (14)
C5—N21.464 (2)N1—O11.219 (2)
C6—H60.9300N1—O21.229 (3)
C7—O51.234 (2)N2—O31.227 (2)
C7—O61.291 (2)N2—O41.228 (2)
C8—C91.490 (3)N3—O81.374 (2)
C8—H8A0.9600N4—O91.387 (2)
C8—H8B0.9600O8—H80.8200
C8—H8C0.9600O9—H90.8200
C9—N31.286 (3)O10—H10D0.8340
C9—C111.480 (3)O10—H10E0.8300
C6—C1—C2121.71 (18)H10A—C10—H10C109.5
C6—C1—N1118.59 (18)H10B—C10—H10C109.5
C2—C1—N1119.69 (18)N4—C11—C9114.23 (17)
C3—C2—C1120.61 (18)N4—C11—C10124.0 (2)
C3—C2—H2119.7C9—C11—C10121.76 (19)
C1—C2—H2119.7O6—Ni1—O794.41 (6)
C2—C3—C4120.23 (17)O6—Ni1—N3174.35 (7)
C2—C3—C7115.97 (17)O7—Ni1—N387.68 (6)
C4—C3—C7123.76 (16)O6—Ni1—N499.08 (6)
O7—C4—C5121.14 (17)O7—Ni1—N4164.71 (6)
O7—C4—C3122.75 (17)N3—Ni1—N478.24 (7)
C5—C4—C3116.11 (17)O6—Ni1—O1094.48 (6)
C6—C5—C4122.77 (17)O7—Ni1—O1094.16 (6)
C6—C5—N2115.37 (17)N3—Ni1—O1090.60 (6)
C4—C5—N2121.86 (17)N4—Ni1—O1091.93 (6)
C1—C6—C5118.48 (18)O1—N1—O2124.0 (2)
C1—C6—H6120.8O1—N1—C1118.2 (2)
C5—C6—H6120.8O2—N1—C1117.80 (19)
O5—C7—O6120.53 (18)O3—N2—O4122.07 (17)
O5—C7—C3119.13 (18)O3—N2—C5117.59 (17)
O6—C7—C3120.31 (16)O4—N2—C5120.32 (16)
C9—C8—H8A109.5C9—N3—O8117.52 (16)
C9—C8—H8B109.5C9—N3—Ni1118.49 (14)
H8A—C8—H8B109.5O8—N3—Ni1123.02 (12)
C9—C8—H8C109.5C11—N4—O9113.77 (16)
H8A—C8—H8C109.5C11—N4—Ni1115.24 (14)
H8B—C8—H8C109.5O9—N4—Ni1130.84 (12)
N3—C9—C11113.05 (17)C7—O6—Ni1128.55 (12)
N3—C9—C8124.9 (2)C4—O7—Ni1126.33 (12)
C11—C9—C8122.05 (19)N3—O8—H8109.5
C11—C10—H10A109.5N4—O9—H9109.5
C11—C10—H10B109.5Ni1—O10—H10D113.0
H10A—C10—H10B109.5Ni1—O10—H10E111.5
C11—C10—H10C109.5H10D—O10—H10E108.6
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O70.822.152.7427 (19)129
O8—H8···O40.822.222.981 (2)155
O9—H9···O10i0.821.862.675 (2)171
O10—H10D···O5ii0.831.862.690 (2)177
O10—H10E···O6i0.831.912.6695 (19)152
O10—H10E···O5i0.832.633.370 (2)150
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O70.822.152.7427 (19)129
O8—H8···O40.822.222.981 (2)155
O9—H9···O10i0.821.862.675 (2)171
O10—H10D···O5ii0.831.862.690 (2)177
O10—H10E···O6i0.831.912.6695 (19)152
O10—H10E···O5i0.832.633.370 (2)150
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z.
Acknowledgements top

The authors are grateful for support from the Key Laboratory of Coordination Chemistry, JingGangShan University, China

references
References top

Bruker (1997). SMART (Version 2.10) and SAINT (Version 7.06A). Bruker AXS Inc., Madison, Wisconsin, USA.

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.