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The Zn atom in the title complex, [Zn(C15H11N2O3)2(C2H5OH)2], lies on an inversion center and has a slightly distorted octa­hedral coordination environment, with four O atoms of the pyrazolone rings in the equatorial plane and two ethanol O atoms in axial positions. The structure displays O—H...N hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052718/hg2149sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052718/hg2149Isup2.hkl
Contains datablock I

CCDC reference: 299689

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.095
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O2 .. 5.87 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C9
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Diethanolbis[4-(2-furoyl)-3-methyl-1-phenyl-1H-pyrazol-5-onato]zinc(II) top
Crystal data top
[Zn(C15H11N2O3)2(C2H6O)2]F(000) = 1440
Mr = 692.04Dx = 1.409 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 21121 reflections
a = 15.366 (3) Åθ = 3.1–27.5°
b = 9.2799 (19) ŵ = 0.81 mm1
c = 22.879 (5) ÅT = 295 K
V = 3262.4 (12) Å3Prism, pale yellow
Z = 40.38 × 0.26 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3728 independent reflections
Radiation source: fine-focus sealed tube2907 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1819
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1212
Tmin = 0.748, Tmax = 0.855l = 2829
29532 measured reflections
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.7953P]
where P = (Fo2 + 2Fc2)/3
3728 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.29 e Å3
1 restraintΔρmin = 0.20 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
Zn10.50000.50000.50000.03957 (10)
O10.80512 (9)0.47345 (18)0.37571 (7)0.0703 (4)
O20.59851 (7)0.44374 (14)0.44176 (5)0.0454 (3)
O30.57060 (7)0.67456 (13)0.51936 (6)0.0462 (3)
O40.56393 (7)0.38331 (15)0.56904 (5)0.0510 (3)
H180.6062 (11)0.333 (2)0.5581 (9)0.076*
N10.70427 (8)0.74863 (15)0.55299 (6)0.0401 (3)
N20.79214 (8)0.72375 (15)0.54172 (6)0.0423 (3)
C10.83007 (17)0.3946 (3)0.32833 (10)0.0813 (7)
H10.88250.40660.30860.098*
C20.77057 (18)0.2997 (3)0.31425 (9)0.0756 (7)
H20.77300.23370.28370.091*
C30.70209 (14)0.3174 (2)0.35471 (9)0.0615 (5)
H30.65040.26550.35580.074*
C40.72556 (10)0.42294 (18)0.39121 (7)0.0434 (4)
C50.67660 (10)0.48587 (17)0.44003 (7)0.0385 (3)
C60.65266 (10)0.66672 (17)0.51765 (7)0.0381 (3)
C70.71013 (9)0.58615 (17)0.48091 (7)0.0378 (3)
C80.79582 (10)0.62881 (19)0.49925 (7)0.0410 (4)
C90.88410 (11)0.5767 (2)0.48159 (9)0.0552 (5)
H9A0.92770.62900.50290.083*
H9B0.89210.59200.44040.083*
H9C0.88910.47580.49010.083*
C100.67903 (10)0.82942 (18)0.60283 (7)0.0417 (4)
C110.59959 (13)0.8043 (3)0.62968 (9)0.0670 (6)
H110.56140.73600.61460.080*
C120.57788 (15)0.8822 (3)0.67919 (9)0.0811 (7)
H120.52470.86540.69730.097*
C130.63308 (17)0.9834 (3)0.70198 (9)0.0720 (6)
H130.61801.03450.73540.086*
C140.71059 (17)1.0079 (2)0.67477 (9)0.0689 (6)
H140.74851.07640.68990.083*
C150.73368 (13)0.9328 (2)0.62510 (8)0.0548 (5)
H150.78630.95230.60670.066*
C160.51941 (15)0.3032 (3)0.61285 (9)0.0679 (6)
H16A0.54640.20930.61700.082*
H16B0.45940.28870.60100.082*
C170.5215 (2)0.3783 (5)0.66902 (12)0.1293 (14)
H17A0.49070.32260.69770.194*
H17B0.49430.47090.66500.194*
H17C0.58080.39070.68120.194*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02395 (14)0.04695 (18)0.04781 (17)0.00158 (10)0.00146 (9)0.00581 (11)
O10.0530 (8)0.0859 (11)0.0720 (9)0.0072 (7)0.0245 (7)0.0134 (8)
O20.0305 (5)0.0522 (7)0.0535 (7)0.0017 (5)0.0025 (5)0.0092 (6)
O30.0260 (5)0.0473 (7)0.0653 (7)0.0004 (5)0.0013 (5)0.0111 (6)
O40.0344 (6)0.0663 (8)0.0523 (7)0.0114 (5)0.0055 (5)0.0048 (6)
N10.0285 (6)0.0434 (7)0.0483 (7)0.0042 (5)0.0022 (5)0.0032 (6)
N20.0272 (6)0.0483 (8)0.0513 (7)0.0047 (5)0.0016 (6)0.0011 (6)
C10.0728 (14)0.102 (2)0.0694 (13)0.0151 (14)0.0340 (12)0.0040 (14)
C20.0963 (18)0.0736 (15)0.0569 (12)0.0231 (14)0.0154 (12)0.0114 (11)
C30.0657 (12)0.0594 (12)0.0594 (11)0.0011 (10)0.0090 (9)0.0101 (9)
C40.0386 (8)0.0450 (9)0.0465 (8)0.0051 (7)0.0060 (7)0.0036 (7)
C50.0319 (7)0.0387 (8)0.0450 (8)0.0031 (6)0.0025 (6)0.0037 (6)
C60.0301 (7)0.0378 (8)0.0465 (8)0.0013 (6)0.0011 (6)0.0011 (7)
C70.0278 (7)0.0396 (8)0.0461 (8)0.0003 (6)0.0039 (6)0.0024 (7)
C80.0304 (7)0.0434 (9)0.0490 (9)0.0030 (6)0.0034 (6)0.0053 (7)
C90.0314 (8)0.0654 (13)0.0690 (11)0.0011 (8)0.0064 (8)0.0052 (10)
C100.0396 (8)0.0455 (9)0.0399 (8)0.0010 (7)0.0006 (6)0.0024 (7)
C110.0507 (10)0.0934 (16)0.0570 (11)0.0146 (11)0.0107 (9)0.0135 (11)
C120.0616 (13)0.126 (2)0.0557 (11)0.0067 (13)0.0175 (10)0.0161 (14)
C130.0845 (16)0.0852 (17)0.0462 (10)0.0081 (12)0.0074 (11)0.0125 (10)
C140.0867 (16)0.0670 (14)0.0530 (11)0.0136 (11)0.0025 (11)0.0132 (10)
C150.0563 (11)0.0571 (11)0.0510 (9)0.0116 (9)0.0057 (8)0.0062 (9)
C160.0612 (11)0.0808 (16)0.0619 (12)0.0097 (11)0.0102 (10)0.0168 (11)
C170.144 (3)0.182 (4)0.0625 (16)0.031 (3)0.0385 (18)0.013 (2)
Geometric parameters (Å, º) top
Zn1—O31.9992 (12)C6—C71.430 (2)
Zn1—O3i1.9992 (12)C7—C81.438 (2)
Zn1—O2i2.0831 (11)C8—C91.496 (2)
Zn1—O22.0831 (11)C9—H9A0.9600
Zn1—O42.1525 (12)C9—H9B0.9600
Zn1—O4i2.1525 (12)C9—H9C0.9600
O1—C41.357 (2)C10—C151.373 (2)
O1—C11.363 (3)C10—C111.386 (2)
O2—C51.2627 (19)C11—C121.385 (3)
O3—C61.2637 (18)C11—H110.9300
O4—C161.423 (2)C12—C131.369 (3)
O4—H180.839 (10)C12—H120.9300
N1—C61.364 (2)C13—C141.363 (3)
N1—N21.3938 (17)C13—H130.9300
N1—C101.419 (2)C14—C151.379 (3)
N2—C81.313 (2)C14—H140.9300
C1—C21.310 (4)C15—H150.9300
C1—H10.9300C16—C171.462 (4)
C2—C31.411 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.336 (3)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.468 (2)C17—H17C0.9600
C5—C71.416 (2)
O3—Zn1—O3i180.0C5—C7—C6120.47 (14)
O3—Zn1—O2i92.83 (5)C5—C7—C8134.97 (15)
O3i—Zn1—O2i87.17 (5)C6—C7—C8104.48 (14)
O3—Zn1—O287.17 (5)N2—C8—C7111.18 (14)
O3i—Zn1—O292.83 (5)N2—C8—C9117.12 (15)
O2i—Zn1—O2180.00 (5)C7—C8—C9131.53 (16)
O3—Zn1—O489.85 (5)C8—C9—H9A109.5
O3i—Zn1—O490.15 (5)C8—C9—H9B109.5
O2i—Zn1—O489.33 (5)H9A—C9—H9B109.5
O2—Zn1—O490.67 (5)C8—C9—H9C109.5
O3—Zn1—O4i90.15 (5)H9A—C9—H9C109.5
O3i—Zn1—O4i89.85 (5)H9B—C9—H9C109.5
O2i—Zn1—O4i90.67 (5)C15—C10—C11119.45 (17)
O2—Zn1—O4i89.33 (5)C15—C10—N1120.02 (15)
O4—Zn1—O4i180.00 (4)C11—C10—N1120.52 (16)
C4—O1—C1106.02 (18)C12—C11—C10119.1 (2)
C5—O2—Zn1129.27 (11)C12—C11—H11120.4
C6—O3—Zn1119.20 (10)C10—C11—H11120.4
C16—O4—Zn1124.07 (12)C13—C12—C11121.4 (2)
C16—O4—H18106.9 (16)C13—C12—H12119.3
Zn1—O4—H18114.6 (16)C11—C12—H12119.3
C6—N1—N2111.18 (13)C14—C13—C12118.8 (2)
C6—N1—C10127.73 (13)C14—C13—H13120.6
N2—N1—C10120.07 (12)C12—C13—H13120.6
C8—N2—N1106.85 (12)C13—C14—C15121.1 (2)
C2—C1—O1111.1 (2)C13—C14—H14119.4
C2—C1—H1124.4C15—C14—H14119.4
O1—C1—H1124.4C10—C15—C14120.09 (19)
C1—C2—C3106.3 (2)C10—C15—H15120.0
C1—C2—H2126.9C14—C15—H15120.0
C3—C2—H2126.9O4—C16—C17111.1 (2)
C4—C3—C2107.1 (2)O4—C16—H16A109.4
C4—C3—H3126.4C17—C16—H16A109.4
C2—C3—H3126.4O4—C16—H16B109.4
C3—C4—O1109.44 (16)C17—C16—H16B109.4
C3—C4—C5128.96 (16)H16A—C16—H16B108.0
O1—C4—C5121.56 (15)C16—C17—H17A109.5
O2—C5—C7121.90 (14)C16—C17—H17B109.5
O2—C5—C4112.81 (14)H17A—C17—H17B109.5
C7—C5—C4125.28 (14)C16—C17—H17C109.5
O3—C6—N1121.99 (14)H17A—C17—H17C109.5
O3—C6—C7131.64 (15)H17B—C17—H17C109.5
N1—C6—C7106.31 (13)
O3—Zn1—O2—C519.63 (14)C10—N1—C6—O313.5 (3)
O3i—Zn1—O2—C5160.37 (14)N2—N1—C6—C70.93 (18)
O4—Zn1—O2—C570.18 (14)C10—N1—C6—C7169.21 (15)
O4i—Zn1—O2—C5109.82 (14)O2—C5—C7—C613.6 (2)
O2i—Zn1—O3—C6147.48 (13)C4—C5—C7—C6164.75 (15)
O2—Zn1—O3—C632.52 (13)O2—C5—C7—C8162.61 (17)
O4—Zn1—O3—C658.16 (13)C4—C5—C7—C819.0 (3)
O4i—Zn1—O3—C6121.84 (13)O3—C6—C7—C55.2 (3)
O3—Zn1—O4—C16129.72 (16)N1—C6—C7—C5177.88 (14)
O3i—Zn1—O4—C1650.28 (16)O3—C6—C7—C8177.58 (18)
O2i—Zn1—O4—C1636.89 (16)N1—C6—C7—C80.65 (17)
O2—Zn1—O4—C16143.11 (16)N1—N2—C8—C70.40 (18)
C6—N1—N2—C80.85 (18)N1—N2—C8—C9176.18 (15)
C10—N1—N2—C8170.15 (14)C5—C7—C8—N2176.78 (17)
C4—O1—C1—C20.0 (3)C6—C7—C8—N20.15 (18)
O1—C1—C2—C30.2 (3)C5—C7—C8—C91.8 (3)
C1—C2—C3—C40.4 (3)C6—C7—C8—C9174.83 (18)
C2—C3—C4—O10.4 (2)C6—N1—C10—C15164.17 (17)
C2—C3—C4—C5178.06 (18)N2—N1—C10—C1528.5 (2)
C1—O1—C4—C30.2 (2)C6—N1—C10—C1116.3 (3)
C1—O1—C4—C5178.14 (18)N2—N1—C10—C11151.08 (18)
Zn1—O2—C5—C70.3 (2)C15—C10—C11—C121.3 (3)
Zn1—O2—C5—C4178.87 (10)N1—C10—C11—C12178.2 (2)
C3—C4—C5—O29.3 (3)C10—C11—C12—C130.1 (4)
O1—C4—C5—O2168.16 (16)C11—C12—C13—C140.5 (4)
C3—C4—C5—C7172.23 (18)C12—C13—C14—C150.0 (4)
O1—C4—C5—C710.3 (3)C11—C10—C15—C141.9 (3)
Zn1—O3—C6—N1149.80 (12)N1—C10—C15—C14177.70 (18)
Zn1—O3—C6—C733.7 (2)C13—C14—C15—C101.2 (3)
N2—N1—C6—O3178.23 (15)Zn1—O4—C16—C17106.1 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H18···N2ii0.84 (1)1.90 (1)2.7339 (17)173 (2)
Symmetry code: (ii) x+3/2, y1/2, z.
 

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