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The crystal structure of the title compound, C18H11ClN2O4, contains intra- and inter­molecular hydrogen bonds that link the ketone and hydroxyl groups. The inter­molecular hydrogen bond results in the formation of a dimer with an R22(12) graph-set motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006538/dn3038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006538/dn3038Isup2.hkl
Contains datablock I

CCDC reference: 600063

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.121
  • Data-to-parameter ratio = 22.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O3 .. O3 .. 2.69 Ang.
Alert level C PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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.

1-(4-Chlorphenyl)-4-(2-furoyl)-3-(2-furyl)-1H-pyrazol-5-ol top
Crystal data top
C18H11ClN2O4F(000) = 728
Mr = 354.74Dx = 1.482 Mg m3
Monoclinic, P21/cMelting point: 464 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.8222 (1) ÅCell parameters from 3811 reflections
b = 19.1260 (3) Åθ = 2.1–30.9°
c = 14.3158 (2) ŵ = 0.27 mm1
β = 93.922 (1)°T = 295 K
V = 1590.41 (4) Å3Prism, yellow
Z = 40.40 × 0.32 × 0.23 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4999 independent reflections
Radiation source: fine-focus sealed tube2944 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ and ω scansθmax = 30.9°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2005)
h = 88
Tmin = 0.901, Tmax = 0.941k = 1927
19802 measured reflectionsl = 2020
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2462P]
where P = (Fo2 + 2Fc2)/3
4999 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.32 e Å3
Special details top

Experimental. The UV spectrum of the molecule in anhydrous ethanol exhibited two absorption bands at 201 nm and 272 nm assigned to intramolecular π -π* and n-π* transitions respectively fromaryl ring·The IR spectrum indicated a very strong asymmetric C=O strectching frequency at 1607 cm-1 and 1527 cm-1 for the pyrazolone ring. Vibrational frequency bands due to intermolecular hydrogen bond O—H···O group of the ligand observed at 3118 cm-1. This analysis result pointed out the ligand existence of enol form in solid state and ethanol solution. However, the 1H NMR data, showed that in CDCl3 solution the ligand exists in keto form·From thermal analysis curves (TG-DTA) of the title compound, an endothermic peak at 160 oC is attributed to the phase transition temperature of the compound. It is thermally stable up to approximately 180 oC and can be completely decomposed at about 670 oC in an air atmosphere, the finally decomposition product is carbon dioxide and water.

1H NMR (CDCl3): δ 6.47 (q, 1H), 6.52 (q, 1H), 6.70 (d, 1H), 6.80 (d, 1H), 7.25 (s, 1H), 7.40 (d, 2H), 7.46 (d, 2H), 7.89 (s, 2H). MS (ESI), m/z (%): 355/353 (70/100, M+). 305 (27), 287 (6).

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
Cl10.16695 (9)0.53955 (3)0.89633 (3)0.06853 (17)
O10.6637 (2)0.49394 (6)0.59135 (8)0.0482 (3)
H10.78100.50050.56400.072*
O20.7415 (2)0.21465 (6)0.50733 (8)0.0530 (3)
O31.0034 (2)0.43071 (7)0.48386 (9)0.0600 (3)
O40.6943 (2)0.30827 (7)0.34199 (8)0.0642 (4)
N10.4254 (2)0.40307 (7)0.62999 (9)0.0412 (3)
N20.3823 (2)0.33331 (7)0.60881 (9)0.0445 (3)
C10.0126 (3)0.49871 (9)0.82043 (11)0.0481 (4)
C20.2134 (3)0.53072 (10)0.79972 (12)0.0531 (4)
H20.25620.57300.82800.064*
C30.3527 (3)0.49992 (9)0.73647 (12)0.0506 (4)
H30.48860.52160.72180.061*
C40.2881 (3)0.43689 (8)0.69544 (10)0.0408 (3)
C50.0869 (3)0.40435 (9)0.71839 (11)0.0472 (4)
H50.04470.36160.69150.057*
C60.0505 (3)0.43551 (10)0.78115 (11)0.0509 (4)
H60.18560.41380.79680.061*
C70.6003 (3)0.42782 (8)0.58177 (10)0.0396 (3)
C80.6731 (3)0.37420 (8)0.52519 (10)0.0397 (3)
C90.5283 (3)0.31681 (8)0.54557 (10)0.0405 (3)
C100.5303 (3)0.24502 (8)0.51172 (10)0.0426 (4)
C110.3650 (3)0.20013 (10)0.48274 (14)0.0586 (5)
H110.20730.20840.47950.070*
C120.4750 (4)0.13735 (10)0.45775 (14)0.0619 (5)
H120.40440.09670.43460.074*
C130.6993 (4)0.14837 (10)0.47415 (13)0.0604 (5)
H130.81270.11550.46440.072*
C140.7645 (5)0.27630 (12)0.26390 (14)0.0803 (7)
H140.67060.24860.22390.096*
C150.9838 (5)0.28975 (12)0.25236 (15)0.0811 (7)
H151.06900.27380.20400.097*
C161.0631 (4)0.33308 (11)0.32800 (13)0.0606 (5)
H161.21050.35140.33910.073*
C170.8832 (3)0.34245 (9)0.38043 (11)0.0451 (4)
C180.8612 (3)0.38416 (8)0.46469 (10)0.0417 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0562 (3)0.0872 (4)0.0640 (3)0.0099 (3)0.0171 (2)0.0242 (2)
O10.0518 (7)0.0417 (6)0.0526 (6)0.0084 (5)0.0156 (5)0.0039 (5)
O20.0492 (7)0.0496 (7)0.0603 (7)0.0098 (6)0.0047 (5)0.0064 (5)
O30.0628 (8)0.0574 (8)0.0622 (7)0.0208 (7)0.0213 (6)0.0092 (6)
O40.0722 (9)0.0733 (9)0.0473 (6)0.0143 (7)0.0066 (6)0.0079 (6)
N10.0420 (7)0.0371 (7)0.0457 (6)0.0009 (6)0.0110 (5)0.0025 (5)
N20.0467 (8)0.0371 (7)0.0511 (7)0.0008 (6)0.0130 (6)0.0016 (6)
C10.0451 (9)0.0570 (10)0.0427 (7)0.0116 (8)0.0073 (7)0.0048 (7)
C20.0557 (11)0.0470 (10)0.0575 (9)0.0023 (8)0.0103 (8)0.0112 (8)
C30.0470 (9)0.0464 (9)0.0597 (9)0.0031 (8)0.0136 (8)0.0065 (8)
C40.0417 (8)0.0412 (8)0.0403 (7)0.0042 (7)0.0080 (6)0.0005 (6)
C50.0479 (9)0.0473 (9)0.0473 (8)0.0026 (8)0.0097 (7)0.0049 (7)
C60.0420 (9)0.0621 (11)0.0496 (8)0.0038 (8)0.0116 (7)0.0032 (8)
C70.0406 (8)0.0394 (8)0.0391 (7)0.0004 (7)0.0053 (6)0.0015 (6)
C80.0409 (8)0.0397 (8)0.0390 (7)0.0005 (7)0.0057 (6)0.0002 (6)
C90.0406 (8)0.0394 (8)0.0419 (7)0.0013 (7)0.0057 (6)0.0019 (6)
C100.0445 (9)0.0406 (8)0.0441 (7)0.0024 (7)0.0124 (6)0.0024 (7)
C110.0497 (10)0.0483 (10)0.0799 (12)0.0068 (9)0.0186 (9)0.0062 (9)
C120.0742 (14)0.0425 (10)0.0713 (12)0.0096 (9)0.0231 (10)0.0072 (9)
C130.0771 (14)0.0443 (10)0.0613 (10)0.0139 (10)0.0159 (10)0.0045 (8)
C140.123 (2)0.0687 (14)0.0505 (10)0.0167 (14)0.0139 (12)0.0143 (10)
C150.122 (2)0.0661 (14)0.0597 (11)0.0124 (14)0.0409 (13)0.0070 (10)
C160.0620 (12)0.0626 (11)0.0598 (10)0.0061 (10)0.0238 (9)0.0033 (9)
C170.0507 (10)0.0431 (9)0.0423 (7)0.0007 (8)0.0098 (7)0.0020 (7)
C180.0436 (9)0.0409 (8)0.0414 (7)0.0004 (7)0.0076 (6)0.0030 (6)
Geometric parameters (Å, º) top
Cl1—C11.7435 (16)C5—H50.9300
O1—C71.3219 (19)C6—H60.9300
O1—H10.8200C7—C81.391 (2)
O2—C101.3655 (19)C8—C91.426 (2)
O2—C131.370 (2)C8—C181.454 (2)
O3—C181.2338 (19)C9—C101.456 (2)
O4—C141.361 (2)C10—C111.334 (2)
O4—C171.363 (2)C11—C121.418 (3)
N1—C71.3541 (19)C11—H110.9300
N1—N21.3874 (18)C12—C131.327 (3)
N1—C41.4273 (18)C12—H120.9300
N2—C91.3216 (19)C13—H130.9300
C1—C21.370 (3)C14—C151.324 (3)
C1—C61.373 (3)C14—H140.9300
C2—C31.387 (2)C15—C161.416 (3)
C2—H20.9300C15—H150.9300
C3—C41.382 (2)C16—C171.342 (2)
C3—H30.9300C16—H160.9300
C4—C51.386 (2)C17—C181.459 (2)
C5—C61.379 (2)
C7—O1—H1109.5N2—C9—C8111.92 (13)
C10—O2—C13105.59 (14)N2—C9—C10118.24 (14)
C14—O4—C17105.53 (16)C8—C9—C10129.73 (14)
C7—N1—N2110.84 (12)C11—C10—O2110.14 (14)
C7—N1—C4130.59 (13)C11—C10—C9133.49 (16)
N2—N1—C4118.58 (12)O2—C10—C9116.37 (14)
C9—N2—N1105.33 (12)C10—C11—C12107.15 (17)
C2—C1—C6120.91 (15)C10—C11—H11126.4
C2—C1—Cl1119.45 (14)C12—C11—H11126.4
C6—C1—Cl1119.64 (13)C13—C12—C11106.06 (17)
C1—C2—C3119.80 (16)C13—C12—H12127.0
C1—C2—H2120.1C11—C12—H12127.0
C3—C2—H2120.1C12—C13—O2111.06 (17)
C4—C3—C2119.58 (16)C12—C13—H13124.5
C4—C3—H3120.2O2—C13—H13124.5
C2—C3—H3120.2C15—C14—O4111.2 (2)
C3—C4—C5120.05 (14)C15—C14—H14124.4
C3—C4—N1121.75 (14)O4—C14—H14124.4
C5—C4—N1118.19 (14)C14—C15—C16106.58 (18)
C6—C5—C4119.88 (16)C14—C15—H15126.7
C6—C5—H5120.1C16—C15—H15126.7
C4—C5—H5120.1C17—C16—C15106.23 (19)
C1—C6—C5119.75 (16)C17—C16—H16126.9
C1—C6—H6120.1C15—C16—H16126.9
C5—C6—H6120.1C16—C17—O4110.46 (15)
O1—C7—N1119.73 (13)C16—C17—C18130.66 (17)
O1—C7—C8132.19 (14)O4—C17—C18118.81 (14)
N1—C7—C8108.00 (13)O3—C18—C8118.90 (14)
C7—C8—C9103.90 (13)O3—C18—C17118.88 (14)
C7—C8—C18121.47 (14)C8—C18—C17122.20 (14)
C9—C8—C18134.62 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.822.232.8562 (16)133
O1—H1···O3i0.821.972.6979 (16)147
Symmetry code: (i) x+2, y+1, z+1.
 

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