Download citation
Download citation
link to html
In the title centrosymmetric binuclear nickel(II) complex, [Ni2(C13H11F2N6O)2(C2H3O2)2], the two Ni atoms, each attached to an acetate ligand, are linked by two fluconazole mol­ecules. Each Ni atom is six-coordinated by two N atoms from the triazole groups and two bridging O atoms from the deprotonated hydroxyl groups of two different fluconazole ligands and two O atoms from the bidentate acetic anion, exhibiting a distorted octa­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026584/hy2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026584/hy2009Isup2.hkl
Contains datablock I

CCDC reference: 609212

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.035
  • wR factor = 0.098
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.99 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 .. 5.41 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O3 .. 5.03 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N5_a .. 5.15 su PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Bis{µ-[2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan- 2-olato}-κ8N2,O:O,N2'-bis[(acetato-κ2O,O')nickel(II)] top
Crystal data top
[Ni2(C13H11F2N6O)2(C2H3O2)2]F(000) = 1728
Mr = 846.06Dx = 1.699 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2925 reflections
a = 13.617 (2) Åθ = 2.3–25.0°
b = 13.883 (2) ŵ = 1.23 mm1
c = 17.501 (3) ÅT = 298 K
V = 3308.4 (9) Å3Prismatic, green
Z = 40.43 × 0.38 × 0.28 mm
Data collection top
Siemens SMART area-detector
diffractometer
2925 independent reflections
Radiation source: fine-focus sealed tube2011 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1610
Tmin = 0.60, Tmax = 0.72k = 1614
16325 measured reflectionsl = 1920
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0325P)2 + 4.3678P]
where P = (Fo2 + 2Fc2)/3
2925 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.30 e Å3
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
Ni10.94928 (3)0.09791 (3)0.49694 (2)0.02500 (14)
F10.86919 (16)0.00937 (16)0.80002 (11)0.0445 (6)
F21.14127 (18)0.15959 (16)0.89126 (12)0.0504 (6)
N10.7873 (2)0.0125 (2)0.56886 (16)0.0318 (7)
N20.8133 (2)0.0306 (2)0.50203 (16)0.0297 (7)
N30.6876 (3)0.0708 (3)0.48232 (19)0.0496 (9)
N41.0376 (2)0.1707 (2)0.66301 (16)0.0313 (7)
N51.0915 (2)0.1786 (2)0.59759 (16)0.0339 (7)
N61.1738 (3)0.2430 (3)0.6962 (2)0.0538 (10)
O10.99186 (17)0.00021 (15)0.57656 (11)0.0250 (5)
O21.07102 (19)0.18788 (18)0.51577 (14)0.0363 (6)
O30.92986 (19)0.21687 (18)0.57231 (14)0.0381 (6)
C10.8348 (3)0.0168 (3)0.63966 (19)0.0321 (8)
H1A0.79820.00880.68260.039*
H1B0.83380.08650.64330.039*
C20.9423 (2)0.0188 (2)0.64432 (18)0.0257 (8)
C30.9399 (3)0.1284 (2)0.6606 (2)0.0306 (8)
H3A0.90750.13950.70920.037*
H3B0.90170.16020.62120.037*
C40.7515 (3)0.0071 (3)0.4528 (2)0.0379 (9)
H40.75190.00910.40120.045*
C50.7133 (3)0.0726 (3)0.5549 (2)0.0431 (10)
H50.68350.11100.59170.052*
C61.1722 (3)0.2225 (3)0.6208 (2)0.0441 (10)
H61.22350.23800.58800.053*
C71.0883 (3)0.2099 (3)0.7201 (2)0.0443 (10)
H71.06640.21360.77030.053*
C80.9933 (2)0.0329 (2)0.71159 (18)0.0256 (8)
C90.9575 (3)0.0337 (2)0.78536 (19)0.0292 (8)
C101.0037 (3)0.0759 (3)0.8468 (2)0.0355 (9)
H100.97650.07520.89550.043*
C111.0918 (3)0.1190 (3)0.8319 (2)0.0352 (9)
C121.1322 (3)0.1242 (3)0.7602 (2)0.0354 (9)
H121.19150.15560.75160.042*
C131.0808 (3)0.0807 (3)0.7006 (2)0.0315 (8)
H131.10660.08400.65150.038*
C141.0173 (3)0.2406 (3)0.5572 (2)0.0368 (9)
C151.0580 (4)0.3333 (3)0.5876 (3)0.0633 (14)
H15A1.00880.36520.61770.095*
H15B1.07680.37400.54580.095*
H15C1.11430.32010.61880.095*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0237 (2)0.0253 (2)0.0260 (2)0.00195 (19)0.00106 (19)0.00007 (19)
F10.0377 (13)0.0638 (15)0.0320 (11)0.0121 (12)0.0072 (10)0.0000 (10)
F20.0581 (17)0.0511 (14)0.0419 (13)0.0017 (12)0.0141 (11)0.0125 (11)
N10.0238 (17)0.0393 (17)0.0324 (16)0.0023 (14)0.0002 (13)0.0020 (14)
N20.0236 (16)0.0351 (16)0.0302 (15)0.0039 (13)0.0019 (14)0.0032 (14)
N30.037 (2)0.059 (2)0.053 (2)0.0104 (18)0.0142 (17)0.0001 (17)
N40.0341 (19)0.0286 (16)0.0312 (16)0.0013 (14)0.0014 (14)0.0029 (13)
N50.0328 (18)0.0329 (17)0.0360 (17)0.0058 (15)0.0042 (15)0.0009 (14)
N60.049 (2)0.062 (2)0.050 (2)0.016 (2)0.0043 (18)0.0123 (18)
O10.0254 (13)0.0291 (12)0.0205 (11)0.0020 (10)0.0029 (10)0.0012 (10)
O20.0346 (15)0.0355 (14)0.0388 (14)0.0022 (12)0.0052 (12)0.0013 (11)
O30.0363 (17)0.0368 (14)0.0413 (15)0.0003 (12)0.0056 (12)0.0053 (12)
C10.026 (2)0.043 (2)0.0271 (18)0.0046 (18)0.0024 (15)0.0018 (16)
C20.0224 (19)0.0318 (19)0.0228 (17)0.0009 (16)0.0034 (14)0.0006 (14)
C30.031 (2)0.0312 (19)0.0293 (19)0.0030 (17)0.0031 (16)0.0033 (15)
C40.030 (2)0.047 (2)0.037 (2)0.0006 (19)0.0088 (18)0.0008 (18)
C50.023 (2)0.054 (3)0.052 (3)0.0119 (19)0.0004 (18)0.009 (2)
C60.035 (2)0.043 (2)0.054 (3)0.009 (2)0.002 (2)0.006 (2)
C70.046 (3)0.051 (3)0.036 (2)0.006 (2)0.004 (2)0.0104 (19)
C80.0245 (19)0.0274 (18)0.0247 (18)0.0036 (16)0.0005 (15)0.0027 (14)
C90.026 (2)0.0300 (19)0.0316 (19)0.0022 (17)0.0046 (16)0.0018 (15)
C100.044 (3)0.035 (2)0.0275 (19)0.0040 (19)0.0044 (18)0.0010 (16)
C110.044 (2)0.029 (2)0.032 (2)0.0046 (18)0.0117 (18)0.0050 (15)
C120.030 (2)0.036 (2)0.040 (2)0.0034 (17)0.0038 (17)0.0009 (17)
C130.029 (2)0.036 (2)0.0292 (19)0.0012 (17)0.0024 (15)0.0010 (16)
C140.040 (2)0.034 (2)0.037 (2)0.0008 (19)0.0018 (19)0.0001 (17)
C150.060 (3)0.052 (3)0.078 (3)0.015 (2)0.006 (3)0.026 (3)
Geometric parameters (Å, º) top
Ni1—O12.033 (2)O3—C141.264 (5)
Ni1—O1i2.034 (2)C1—C21.547 (5)
Ni1—N5i2.073 (3)C1—H1A0.9700
Ni1—N22.077 (3)C1—H1B0.9700
Ni1—O22.102 (3)C2—C81.544 (5)
Ni1—O32.130 (2)C2—C31.548 (5)
Ni1—Ni1i3.0512 (9)C3—H3A0.9700
F1—C91.367 (4)C3—H3B0.9700
F2—C111.360 (4)C4—H40.9300
N1—C51.331 (5)C5—H50.9300
N1—N21.360 (4)C6—H60.9300
N1—C11.456 (4)C7—H70.9300
N2—C41.313 (4)C8—C131.377 (5)
N3—C51.318 (5)C8—C91.380 (4)
N3—C41.344 (5)C9—C101.377 (5)
N4—C71.331 (5)C10—C111.366 (5)
N4—N51.364 (4)C10—H100.9300
N4—C31.455 (4)C11—C121.373 (5)
N5—C61.320 (5)C12—C131.393 (5)
N5—Ni1i2.073 (3)C12—H120.9300
N6—C71.319 (5)C13—H130.9300
N6—C61.349 (5)C14—C151.498 (5)
O1—C21.389 (4)C15—H15A0.9600
O1—Ni1i2.034 (2)C15—H15B0.9600
O2—C141.263 (4)C15—H15C0.9600
O1—Ni1—O1i82.78 (9)O1—C2—C3110.5 (3)
O1—Ni1—N5i170.08 (10)C8—C2—C3109.0 (3)
O1i—Ni1—N5i87.76 (10)C1—C2—C3107.7 (3)
O1—Ni1—N285.60 (10)N4—C3—C2112.5 (3)
O1i—Ni1—N294.49 (10)N4—C3—H3A109.1
N5i—Ni1—N292.20 (12)C2—C3—H3A109.1
O1—Ni1—O293.78 (9)N4—C3—H3B109.1
O1i—Ni1—O2100.65 (9)C2—C3—H3B109.1
N5i—Ni1—O290.89 (11)H3A—C3—H3B107.8
N2—Ni1—O2164.66 (10)N2—C4—N3115.1 (3)
O1—Ni1—O397.50 (9)N2—C4—H4122.4
O1i—Ni1—O3163.26 (10)N3—C4—H4122.4
N5i—Ni1—O392.42 (11)N3—C5—N1111.5 (4)
N2—Ni1—O3102.23 (11)N3—C5—H5124.2
O2—Ni1—O362.61 (10)N1—C5—H5124.2
O1—Ni1—Ni1i41.40 (6)N5—C6—N6114.3 (4)
O1i—Ni1—Ni1i41.38 (6)N5—C6—H6122.8
N5i—Ni1—Ni1i129.08 (8)N6—C6—H6122.8
N2—Ni1—Ni1i90.06 (8)N6—C7—N4111.2 (4)
O2—Ni1—Ni1i99.61 (7)N6—C7—H7124.4
O3—Ni1—Ni1i136.49 (7)N4—C7—H7124.4
C5—N1—N2108.3 (3)C13—C8—C9115.7 (3)
C5—N1—C1131.9 (3)C13—C8—C2120.5 (3)
N2—N1—C1119.6 (3)C9—C8—C2123.9 (3)
C4—N2—N1102.9 (3)F1—C9—C10116.2 (3)
C4—N2—Ni1136.3 (3)F1—C9—C8118.9 (3)
N1—N2—Ni1117.8 (2)C10—C9—C8124.9 (3)
C5—N3—C4102.2 (3)C11—C10—C9116.1 (3)
C7—N4—N5108.5 (3)C11—C10—H10122.0
C7—N4—C3131.4 (3)C9—C10—H10122.0
N5—N4—C3120.0 (3)F2—C11—C10118.1 (3)
C6—N5—N4103.1 (3)F2—C11—C12118.5 (4)
C6—N5—Ni1i135.9 (3)C10—C11—C12123.3 (3)
N4—N5—Ni1i118.8 (2)C11—C12—C13117.4 (4)
C7—N6—C6102.8 (3)C11—C12—H12121.3
C2—O1—Ni1124.8 (2)C13—C12—H12121.3
C2—O1—Ni1i127.43 (19)C8—C13—C12122.6 (3)
Ni1—O1—Ni1i97.22 (9)C8—C13—H13118.7
C14—O2—Ni188.7 (2)C12—C13—H13118.7
C14—O3—Ni187.5 (2)O2—C14—O3120.9 (3)
N1—C1—C2112.1 (3)O2—C14—C15119.2 (4)
N1—C1—H1A109.2O3—C14—C15119.9 (4)
C2—C1—H1A109.2C14—C15—H15A109.5
N1—C1—H1B109.2C14—C15—H15B109.5
C2—C1—H1B109.2H15A—C15—H15B109.5
H1A—C1—H1B107.9C14—C15—H15C109.5
O1—C2—C8110.2 (3)H15A—C15—H15C109.5
O1—C2—C1110.8 (3)H15B—C15—H15C109.5
C8—C2—C1108.5 (3)
C5—N1—N2—C40.4 (4)Ni1i—O1—C2—C1117.0 (3)
C1—N1—N2—C4175.0 (3)Ni1—O1—C2—C3138.8 (2)
C5—N1—N2—Ni1163.0 (2)Ni1i—O1—C2—C32.3 (4)
C1—N1—N2—Ni121.5 (4)N1—C1—C2—O146.8 (4)
O1—Ni1—N2—C4127.7 (4)N1—C1—C2—C8168.0 (3)
O1i—Ni1—N2—C445.3 (4)N1—C1—C2—C374.1 (3)
N5i—Ni1—N2—C442.6 (4)C7—N4—C3—C2113.5 (4)
O2—Ni1—N2—C4144.1 (4)N5—N4—C3—C269.6 (4)
O3—Ni1—N2—C4135.6 (3)O1—C2—C3—N456.4 (4)
Ni1i—Ni1—N2—C486.5 (3)C8—C2—C3—N464.9 (3)
O1—Ni1—N2—N128.7 (2)C1—C2—C3—N4177.6 (3)
O1i—Ni1—N2—N1111.0 (2)N1—N2—C4—N30.1 (4)
N5i—Ni1—N2—N1161.0 (2)Ni1—N2—C4—N3158.8 (3)
O2—Ni1—N2—N159.6 (5)C5—N3—C4—N20.7 (5)
O3—Ni1—N2—N168.1 (2)C4—N3—C5—N10.9 (5)
Ni1i—Ni1—N2—N169.9 (2)N2—N1—C5—N30.9 (4)
C7—N4—N5—C60.2 (4)C1—N1—C5—N3173.8 (4)
C3—N4—N5—C6177.7 (3)N4—N5—C6—N60.2 (4)
C7—N4—N5—Ni1i165.9 (3)Ni1i—N5—C6—N6161.7 (3)
C3—N4—N5—Ni1i16.6 (4)C7—N6—C6—N50.5 (5)
O1i—Ni1—O1—C2146.6 (3)C6—N6—C7—N40.6 (5)
N2—Ni1—O1—C251.5 (2)N5—N4—C7—N60.5 (5)
O2—Ni1—O1—C2113.2 (2)C3—N4—C7—N6177.7 (4)
O3—Ni1—O1—C250.3 (2)O1—C2—C8—C135.9 (4)
Ni1i—Ni1—O1—C2146.6 (3)C1—C2—C8—C13127.4 (3)
O1i—Ni1—O1—Ni1i0.0C3—C2—C8—C13115.6 (3)
N2—Ni1—O1—Ni1i95.10 (11)O1—C2—C8—C9175.4 (3)
O2—Ni1—O1—Ni1i100.27 (10)C1—C2—C8—C953.8 (4)
O3—Ni1—O1—Ni1i163.12 (10)C3—C2—C8—C963.2 (4)
O1—Ni1—O2—C1499.3 (2)C13—C8—C9—F1177.7 (3)
O1i—Ni1—O2—C14177.3 (2)C2—C8—C9—F13.5 (5)
N5i—Ni1—O2—C1489.4 (2)C13—C8—C9—C101.6 (5)
N2—Ni1—O2—C1412.2 (5)C2—C8—C9—C10177.3 (3)
O3—Ni1—O2—C142.8 (2)F1—C9—C10—C11179.9 (3)
Ni1i—Ni1—O2—C14140.6 (2)C8—C9—C10—C110.6 (6)
O1—Ni1—O3—C1493.2 (2)C9—C10—C11—F2178.4 (3)
O1i—Ni1—O3—C143.4 (4)C9—C10—C11—C122.4 (6)
N5i—Ni1—O3—C1486.9 (2)F2—C11—C12—C13179.0 (3)
N2—Ni1—O3—C14179.7 (2)C10—C11—C12—C131.8 (6)
O2—Ni1—O3—C142.8 (2)C9—C8—C13—C122.2 (5)
Ni1i—Ni1—O3—C1477.0 (2)C2—C8—C13—C12176.7 (3)
C5—N1—C1—C2113.5 (4)C11—C12—C13—C80.6 (5)
N2—N1—C1—C272.3 (4)Ni1—O2—C14—O34.9 (4)
Ni1—O1—C2—C8100.6 (3)Ni1—O2—C14—C15174.1 (3)
Ni1i—O1—C2—C8122.9 (2)Ni1—O3—C14—O24.9 (4)
Ni1—O1—C2—C119.5 (4)Ni1—O3—C14—C15174.2 (4)
Symmetry code: (i) x+2, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds