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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.
Supporting information
CCDC reference: 674058
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.026
- wR factor = 0.073
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ni1 - O6 .. 10.05 su
PLAT417_ALERT_2_B Short Inter D-H..H-D H9 .. H10E .. 2.06 Ang.
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O7 .. 6.03 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N3 .. 8.35 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N4 .. 5.73 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10E .. O5 .. 2.63 Ang.
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.11
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
1 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
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.
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.
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).
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 = 418.94 | Dx = 1.804 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7541 reflections |
a = 12.476 (2) Å | θ = 0.9–28.3° |
b = 7.0786 (14) Å | µ = 1.32 mm−1 |
c = 17.929 (4) Å | T = 293 K |
β = 103.014 (3)° | Block, blue |
V = 1542.7 (5) Å3 | 0.28 × 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 tube | Rint = 0.019 |
Graphite monochromator | θmax = 25.5°, θmin = 2.3° |
ϕ and ω scans | h = −14→15 |
9276 measured reflections | k = −8→8 |
2824 independent reflections | l = −21→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.073 | H-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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Crystal data top
[Ni(C7H2N2O7)(C4H8N2O2)(H2O)] | V = 1542.7 (5) Å3 |
Mr = 418.94 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.476 (2) Å | µ = 1.32 mm−1 |
b = 7.0786 (14) Å | T = 293 K |
c = 17.929 (4) Å | 0.28 × 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 reflections | Rint = 0.019 |
2824 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.073 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.20 e Å−3 |
2824 reflections | Δρmin = −0.26 e Å−3 |
239 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 | Uiso*/Ueq | |
C1 | 0.38531 (16) | 0.8249 (3) | −0.15675 (10) | 0.0431 (4) | |
C2 | 0.29061 (16) | 0.8484 (3) | −0.12964 (11) | 0.0429 (4) | |
H2 | 0.2494 | 0.9584 | −0.1411 | 0.051* | |
C3 | 0.25681 (15) | 0.7100 (3) | −0.08576 (10) | 0.0389 (4) | |
C4 | 0.31731 (15) | 0.5365 (3) | −0.07013 (10) | 0.0377 (4) | |
C5 | 0.41420 (15) | 0.5225 (3) | −0.09925 (10) | 0.0379 (4) | |
C6 | 0.44881 (16) | 0.6656 (3) | −0.14101 (10) | 0.0410 (4) | |
H6 | 0.5137 | 0.6539 | −0.1580 | 0.049* | |
C7 | 0.15838 (16) | 0.7567 (3) | −0.05465 (11) | 0.0434 (4) | |
C8 | 0.2461 (2) | −0.0792 (3) | 0.17163 (15) | 0.0625 (6) | |
H8A | 0.2909 | −0.1448 | 0.1429 | 0.094* | |
H8B | 0.1793 | −0.1485 | 0.1692 | 0.094* | |
H8C | 0.2855 | −0.0681 | 0.2240 | 0.094* | |
C9 | 0.21937 (16) | 0.1128 (3) | 0.13860 (11) | 0.0441 (5) | |
C10 | 0.1053 (2) | 0.2006 (4) | 0.23813 (14) | 0.0690 (7) | |
H10A | 0.0894 | 0.3166 | 0.2612 | 0.104* | |
H10B | 0.1610 | 0.1325 | 0.2736 | 0.104* | |
H10C | 0.0397 | 0.1253 | 0.2250 | 0.104* | |
C11 | 0.14518 (16) | 0.2430 (3) | 0.16752 (11) | 0.0461 (5) | |
Ni1 | 0.19075 (2) | 0.41717 (3) | 0.035803 (14) | 0.04002 (10) | |
N1 | 0.41838 (17) | 0.9713 (3) | −0.20418 (10) | 0.0561 (5) | |
N2 | 0.48544 (14) | 0.3559 (2) | −0.08555 (9) | 0.0455 (4) | |
N3 | 0.25549 (13) | 0.1823 (2) | 0.08265 (9) | 0.0438 (4) | |
N4 | 0.11866 (14) | 0.3919 (2) | 0.12644 (10) | 0.0460 (4) | |
O1 | 0.50896 (16) | 0.9592 (3) | −0.21874 (10) | 0.0769 (5) | |
O2 | 0.35279 (17) | 1.0994 (3) | −0.22726 (12) | 0.0866 (6) | |
O3 | 0.57504 (13) | 0.3662 (3) | −0.10271 (11) | 0.0724 (5) | |
O4 | 0.45619 (13) | 0.2136 (2) | −0.05635 (10) | 0.0664 (5) | |
O5 | 0.10174 (13) | 0.89514 (19) | −0.08015 (10) | 0.0573 (4) | |
O6 | 0.13486 (12) | 0.6563 (2) | −0.00039 (9) | 0.0524 (4) | |
O7 | 0.28663 (13) | 0.39915 (19) | −0.03220 (9) | 0.0517 (4) | |
O8 | 0.32368 (13) | 0.0709 (2) | 0.05091 (9) | 0.0546 (4) | |
H8 | 0.3413 | 0.1281 | 0.0157 | 0.082* | |
O9 | 0.05069 (15) | 0.5146 (2) | 0.15476 (9) | 0.0638 (4) | |
H9 | 0.0265 | 0.5949 | 0.1224 | 0.096* | |
O10 | 0.04723 (11) | 0.24631 (18) | −0.04489 (8) | 0.0496 (3) | |
H10D | 0.0660 | 0.1377 | −0.0548 | 0.074* | |
H10E | −0.0077 | 0.2383 | −0.0261 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0520 (12) | 0.0435 (11) | 0.0355 (9) | −0.0072 (9) | 0.0136 (8) | 0.0006 (8) |
C2 | 0.0471 (11) | 0.0367 (10) | 0.0453 (10) | 0.0010 (8) | 0.0112 (9) | 0.0015 (8) |
C3 | 0.0413 (10) | 0.0338 (9) | 0.0437 (10) | 0.0015 (8) | 0.0137 (8) | −0.0008 (7) |
C4 | 0.0418 (11) | 0.0338 (9) | 0.0399 (9) | 0.0002 (8) | 0.0144 (8) | −0.0021 (7) |
C5 | 0.0396 (10) | 0.0376 (9) | 0.0373 (9) | 0.0016 (8) | 0.0108 (8) | −0.0057 (8) |
C6 | 0.0418 (11) | 0.0480 (11) | 0.0363 (9) | −0.0042 (9) | 0.0155 (8) | −0.0067 (8) |
C7 | 0.0452 (11) | 0.0310 (9) | 0.0572 (12) | 0.0029 (8) | 0.0178 (9) | −0.0011 (8) |
C8 | 0.0626 (15) | 0.0570 (14) | 0.0707 (15) | 0.0121 (11) | 0.0208 (12) | 0.0219 (11) |
C9 | 0.0389 (11) | 0.0460 (11) | 0.0468 (11) | 0.0001 (8) | 0.0087 (9) | 0.0061 (8) |
C10 | 0.0776 (17) | 0.0758 (17) | 0.0639 (14) | 0.0064 (13) | 0.0372 (13) | 0.0187 (12) |
C11 | 0.0435 (11) | 0.0496 (11) | 0.0480 (11) | 0.0010 (9) | 0.0163 (9) | 0.0065 (9) |
Ni1 | 0.04354 (17) | 0.03448 (15) | 0.04867 (16) | 0.00837 (10) | 0.02439 (12) | 0.00723 (10) |
N1 | 0.0639 (13) | 0.0591 (12) | 0.0465 (10) | −0.0081 (10) | 0.0147 (9) | 0.0104 (8) |
N2 | 0.0438 (10) | 0.0474 (9) | 0.0486 (9) | 0.0070 (8) | 0.0171 (8) | −0.0047 (7) |
N3 | 0.0400 (9) | 0.0443 (9) | 0.0497 (9) | 0.0077 (7) | 0.0159 (7) | 0.0035 (7) |
N4 | 0.0463 (10) | 0.0469 (10) | 0.0503 (9) | 0.0057 (7) | 0.0223 (8) | 0.0013 (7) |
O1 | 0.0749 (12) | 0.0903 (13) | 0.0777 (11) | −0.0063 (10) | 0.0429 (10) | 0.0231 (10) |
O2 | 0.0819 (13) | 0.0832 (14) | 0.0964 (14) | 0.0058 (10) | 0.0239 (11) | 0.0487 (11) |
O3 | 0.0478 (10) | 0.0778 (11) | 0.1014 (13) | 0.0172 (8) | 0.0373 (9) | 0.0104 (10) |
O4 | 0.0708 (11) | 0.0463 (9) | 0.0928 (12) | 0.0153 (8) | 0.0411 (9) | 0.0107 (8) |
O5 | 0.0529 (9) | 0.0391 (8) | 0.0841 (11) | 0.0139 (6) | 0.0245 (8) | 0.0084 (7) |
O6 | 0.0531 (9) | 0.0430 (8) | 0.0719 (9) | 0.0112 (7) | 0.0366 (8) | 0.0088 (7) |
O7 | 0.0581 (9) | 0.0377 (8) | 0.0708 (10) | 0.0111 (6) | 0.0387 (8) | 0.0115 (6) |
O8 | 0.0564 (9) | 0.0518 (9) | 0.0622 (9) | 0.0179 (7) | 0.0271 (7) | 0.0063 (7) |
O9 | 0.0776 (11) | 0.0594 (10) | 0.0662 (10) | 0.0232 (9) | 0.0413 (9) | 0.0076 (8) |
O10 | 0.0461 (8) | 0.0407 (7) | 0.0676 (9) | 0.0087 (6) | 0.0245 (7) | 0.0004 (7) |
Geometric parameters (Å, º) top
C1—C6 | 1.370 (3) | C10—C11 | 1.492 (3) |
C1—C2 | 1.385 (3) | C10—H10A | 0.9600 |
C1—N1 | 1.458 (3) | C10—H10B | 0.9600 |
C2—C3 | 1.380 (3) | C10—H10C | 0.9600 |
C2—H2 | 0.9300 | C11—N4 | 1.286 (3) |
C3—C4 | 1.436 (3) | Ni1—O6 | 1.8889 (14) |
C3—C7 | 1.495 (3) | Ni1—O7 | 1.8949 (14) |
C4—O7 | 1.293 (2) | Ni1—N3 | 1.9538 (16) |
C4—C5 | 1.424 (3) | Ni1—N4 | 2.0347 (17) |
C5—C6 | 1.385 (3) | Ni1—O10 | 2.3654 (14) |
C5—N2 | 1.464 (2) | N1—O1 | 1.219 (2) |
C6—H6 | 0.9300 | N1—O2 | 1.229 (3) |
C7—O5 | 1.234 (2) | N2—O3 | 1.227 (2) |
C7—O6 | 1.291 (2) | N2—O4 | 1.228 (2) |
C8—C9 | 1.490 (3) | N3—O8 | 1.374 (2) |
C8—H8A | 0.9600 | N4—O9 | 1.387 (2) |
C8—H8B | 0.9600 | O8—H8 | 0.8200 |
C8—H8C | 0.9600 | O9—H9 | 0.8200 |
C9—N3 | 1.286 (3) | O10—H10D | 0.8340 |
C9—C11 | 1.480 (3) | O10—H10E | 0.8300 |
| | | |
C6—C1—C2 | 121.71 (18) | H10A—C10—H10C | 109.5 |
C6—C1—N1 | 118.59 (18) | H10B—C10—H10C | 109.5 |
C2—C1—N1 | 119.69 (18) | N4—C11—C9 | 114.23 (17) |
C3—C2—C1 | 120.61 (18) | N4—C11—C10 | 124.0 (2) |
C3—C2—H2 | 119.7 | C9—C11—C10 | 121.76 (19) |
C1—C2—H2 | 119.7 | O6—Ni1—O7 | 94.41 (6) |
C2—C3—C4 | 120.23 (17) | O6—Ni1—N3 | 174.35 (7) |
C2—C3—C7 | 115.97 (17) | O7—Ni1—N3 | 87.68 (6) |
C4—C3—C7 | 123.76 (16) | O6—Ni1—N4 | 99.08 (6) |
O7—C4—C5 | 121.14 (17) | O7—Ni1—N4 | 164.71 (6) |
O7—C4—C3 | 122.75 (17) | N3—Ni1—N4 | 78.24 (7) |
C5—C4—C3 | 116.11 (17) | O6—Ni1—O10 | 94.48 (6) |
C6—C5—C4 | 122.77 (17) | O7—Ni1—O10 | 94.16 (6) |
C6—C5—N2 | 115.37 (17) | N3—Ni1—O10 | 90.60 (6) |
C4—C5—N2 | 121.86 (17) | N4—Ni1—O10 | 91.93 (6) |
C1—C6—C5 | 118.48 (18) | O1—N1—O2 | 124.0 (2) |
C1—C6—H6 | 120.8 | O1—N1—C1 | 118.2 (2) |
C5—C6—H6 | 120.8 | O2—N1—C1 | 117.80 (19) |
O5—C7—O6 | 120.53 (18) | O3—N2—O4 | 122.07 (17) |
O5—C7—C3 | 119.13 (18) | O3—N2—C5 | 117.59 (17) |
O6—C7—C3 | 120.31 (16) | O4—N2—C5 | 120.32 (16) |
C9—C8—H8A | 109.5 | C9—N3—O8 | 117.52 (16) |
C9—C8—H8B | 109.5 | C9—N3—Ni1 | 118.49 (14) |
H8A—C8—H8B | 109.5 | O8—N3—Ni1 | 123.02 (12) |
C9—C8—H8C | 109.5 | C11—N4—O9 | 113.77 (16) |
H8A—C8—H8C | 109.5 | C11—N4—Ni1 | 115.24 (14) |
H8B—C8—H8C | 109.5 | O9—N4—Ni1 | 130.84 (12) |
N3—C9—C11 | 113.05 (17) | C7—O6—Ni1 | 128.55 (12) |
N3—C9—C8 | 124.9 (2) | C4—O7—Ni1 | 126.33 (12) |
C11—C9—C8 | 122.05 (19) | N3—O8—H8 | 109.5 |
C11—C10—H10A | 109.5 | N4—O9—H9 | 109.5 |
C11—C10—H10B | 109.5 | Ni1—O10—H10D | 113.0 |
H10A—C10—H10B | 109.5 | Ni1—O10—H10E | 111.5 |
C11—C10—H10C | 109.5 | H10D—O10—H10E | 108.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O7 | 0.82 | 2.15 | 2.7427 (19) | 129 |
O8—H8···O4 | 0.82 | 2.22 | 2.981 (2) | 155 |
O9—H9···O10i | 0.82 | 1.86 | 2.675 (2) | 171 |
O10—H10D···O5ii | 0.83 | 1.86 | 2.690 (2) | 177 |
O10—H10E···O6i | 0.83 | 1.91 | 2.6695 (19) | 152 |
O10—H10E···O5i | 0.83 | 2.63 | 3.370 (2) | 150 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z. |
Experimental details
Crystal data |
Chemical formula | [Ni(C7H2N2O7)(C4H8N2O2)(H2O)] |
Mr | 418.94 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.476 (2), 7.0786 (14), 17.929 (4) |
β (°) | 103.014 (3) |
V (Å3) | 1542.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.32 |
Crystal size (mm) | 0.28 × 0.26 × 0.22 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9276, 2824, 2426 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.605 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.073, 1.07 |
No. of reflections | 2824 |
No. of parameters | 239 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.26 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O7 | 0.82 | 2.15 | 2.7427 (19) | 129.2 |
O8—H8···O4 | 0.82 | 2.22 | 2.981 (2) | 154.5 |
O9—H9···O10i | 0.82 | 1.86 | 2.675 (2) | 171.3 |
O10—H10D···O5ii | 0.83 | 1.86 | 2.690 (2) | 177.4 |
O10—H10E···O6i | 0.83 | 1.91 | 2.6695 (19) | 151.9 |
O10—H10E···O5i | 0.83 | 2.63 | 3.370 (2) | 149.6 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x, y−1, z. |
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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).