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The molecule of the title compound, C14H15N3O2S, is non-planar; the dihedral angle between the two fur­yl rings is 88.4 (2)°. The crystal structure is stabilized by one C—H...π inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501915X/is6090sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501915X/is6090Isup2.hkl
Contains datablock I

CCDC reference: 277707

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.139
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C13 - C14 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(N-Ethylthiocarbamoyl)-3,5-di-2-furyl-2-pyrazoline top
Crystal data top
C14H15N3O2SF(000) = 608
Mr = 289.35Dx = 1.330 Mg m3
Monoclinic, P21/cMelting point = 408–409 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.0192 (4) ÅCell parameters from 9837 reflections
b = 22.1771 (10) Åθ = 1.8–27.2°
c = 10.5972 (7) ŵ = 0.23 mm1
β = 119.541 (4)°T = 293 K
V = 1435.17 (14) Å3Prism, yellow
Z = 40.56 × 0.50 × 0.43 mm
Data collection top
Stoe IPDS-2
diffractometer
2808 independent reflections
Radiation source: fine-focus sealed tube2420 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.8°
ω scan rotationh = 88
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 2427
Tmin = 0.879, Tmax = 0.879l = 1313
13798 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1115P)2 + 0.5302P]
where P = (Fo2 + 2Fc2)/3
2808 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.36 e Å3
Special details top

Experimental. In thin layer chromotography S-1, S-2 and S-4 solvent systems, Rf values were obtained 0.28, 0.56 and 0.38, respectively.

In the UV spectra of compound three absorption maxima were observed at 200, 217, 328 nm with logε values of 4.35, 4.41 and 4.63, respectively.

In the IR spectra, peaks were detected at N—H streching (3350 cm-1), aromatic C—H streching (3118 cm-1), aliphatic C—H streching (2978 cm-1), CN streching (1518-1), CC streching (1420-1), pyrazoline C4—H streching (1390-1), CS streching (1335-1), C5—N1 streching (1179-1), furan C—O—C streching (1071-1) and C—H deformation (808.751-1).

In 1H NMR spectra, peaks were observed at δ (CDCl3) 3.21ppm (1H; dd; HA,JAB: 17.41 Hz, JAX: 3.46 Hz), 3.45 p.p.m. (1H; dd; HB,JAB: 17.43 Hz, JBX: 11.42 Hz), 6.10 p.p.m. (1H; dd; HX,JAX: 3.39 Hz, JBX: 11.41 Hz), 1.25 p.p.m. (3H; t; CH3,JAB: 7.24 Hz), 3.62 p.p.m. (2H; m; CH2), 6.22 p.p.m. (1H; m; 5-furan H3), 6.34 p.p.m. (1H; d; 5-furan H4,JAB: 3.20 Hz), 6.47 p.p.m. (1H; m; 3-furan H3), 6.72 p.p.m. (1H; d; 3-furan H4, JAB: 3.42 Hz), 7.15–7.55 p.p.m. (2H; m; 3- and 5-furan H5), and 7.23 p.p.m. (1H; b; NH).

In mass spectra of the compound, observed values are below: m/e 289 (M+, 100%), 260 (M—C2H5), 202 (M—C3H5NS), 173 (M—C3H6N3S) and 94 (M—C9H11N2OS).

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
C120.1048 (3)0.67841 (9)0.8059 (2)0.0563 (5)
C140.2853 (5)0.79673 (16)0.6095 (3)0.1063 (10)
H14A0.37880.82260.62760.159*
H14B0.37320.76880.53360.159*
H14C0.19940.82060.58040.159*
C10.4721 (3)0.62884 (10)0.5456 (2)0.0603 (5)
C20.6292 (4)0.59948 (14)0.5337 (3)0.0854 (7)
H20.72500.57080.59740.103*
C30.6206 (6)0.62073 (17)0.4049 (4)0.1030 (10)
H30.71060.60880.36810.124*
C40.4603 (5)0.66073 (16)0.3472 (3)0.0965 (9)
H40.41870.68160.26130.116*
C50.4059 (3)0.62576 (9)0.6533 (2)0.0536 (4)
C60.5107 (3)0.58420 (11)0.7812 (2)0.0607 (5)
C70.3563 (3)0.58929 (9)0.8441 (2)0.0551 (5)
C80.2115 (3)0.53632 (9)0.8135 (2)0.0549 (4)
C90.1471 (4)0.50390 (11)0.8920 (3)0.0768 (6)
H90.18850.50990.98910.092*
C100.0036 (5)0.45872 (11)0.7995 (4)0.0871 (8)
H100.06740.42940.82400.104*
C110.0096 (4)0.46614 (12)0.6724 (3)0.0851 (7)
H110.09300.44230.59130.102*
C130.1435 (5)0.76427 (14)0.7385 (3)0.0964 (9)
H13A0.23110.74090.76850.116*
H13B0.05720.79270.81530.116*
N10.2314 (3)0.64411 (7)0.76951 (18)0.0573 (4)
N20.2540 (3)0.65925 (7)0.64996 (18)0.0556 (4)
N30.0037 (3)0.72381 (8)0.7184 (2)0.0701 (5)
H3A0.02500.72990.64610.084*
O10.3645 (3)0.66708 (8)0.43141 (18)0.0802 (5)
O20.1167 (3)0.51387 (7)0.67627 (16)0.0700 (4)
S10.08539 (10)0.66235 (3)0.95363 (7)0.0732 (2)
H6A0.520 (4)0.5444 (11)0.751 (3)0.072 (7)*
H6B0.658 (4)0.5979 (11)0.849 (3)0.076 (7)*
H70.429 (3)0.5961 (9)0.941 (2)0.060 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C120.0535 (10)0.0602 (11)0.0604 (11)0.0059 (8)0.0320 (9)0.0092 (9)
C140.109 (2)0.122 (3)0.109 (2)0.051 (2)0.0697 (19)0.0250 (19)
C10.0563 (10)0.0677 (12)0.0637 (11)0.0046 (9)0.0347 (9)0.0012 (9)
C20.0747 (15)0.1003 (19)0.1016 (19)0.0132 (13)0.0591 (15)0.0071 (15)
C30.106 (2)0.133 (3)0.111 (2)0.003 (2)0.085 (2)0.011 (2)
C40.105 (2)0.133 (3)0.0795 (17)0.0064 (19)0.0669 (17)0.0034 (16)
C50.0492 (9)0.0562 (10)0.0586 (10)0.0035 (8)0.0290 (8)0.0004 (8)
C60.0491 (10)0.0671 (13)0.0671 (12)0.0029 (9)0.0294 (9)0.0092 (10)
C70.0523 (10)0.0621 (11)0.0498 (10)0.0012 (8)0.0243 (8)0.0052 (8)
C80.0551 (10)0.0552 (10)0.0555 (10)0.0039 (8)0.0281 (8)0.0086 (8)
C90.0925 (16)0.0709 (14)0.0777 (14)0.0014 (12)0.0501 (13)0.0175 (11)
C100.0962 (18)0.0587 (13)0.125 (2)0.0109 (12)0.0689 (18)0.0093 (14)
C110.0840 (16)0.0677 (14)0.106 (2)0.0227 (12)0.0491 (15)0.0129 (14)
C130.100 (2)0.104 (2)0.0917 (18)0.0385 (17)0.0516 (16)0.0034 (16)
N10.0672 (10)0.0550 (9)0.0631 (9)0.0045 (8)0.0425 (8)0.0072 (7)
N20.0628 (9)0.0552 (9)0.0597 (9)0.0015 (7)0.0386 (8)0.0047 (7)
N30.0772 (11)0.0722 (11)0.0686 (11)0.0178 (9)0.0418 (9)0.0008 (9)
O10.0847 (11)0.1012 (12)0.0716 (10)0.0113 (9)0.0515 (9)0.0159 (9)
O20.0762 (9)0.0689 (9)0.0674 (9)0.0146 (7)0.0373 (8)0.0060 (7)
S10.0769 (4)0.0893 (4)0.0702 (4)0.0088 (3)0.0493 (3)0.0077 (3)
Geometric parameters (Å, º) top
C12—N31.315 (3)C6—H6A0.95 (2)
C12—N11.362 (2)C6—H6B0.97 (2)
C12—S11.676 (2)C7—N11.479 (3)
C14—C131.427 (4)C7—C81.481 (3)
C14—H14A0.9600C7—H70.90 (2)
C14—H14B0.9600C8—C91.336 (3)
C14—H14C0.9600C8—O21.361 (2)
C1—C21.339 (3)C9—C101.416 (4)
C1—O11.361 (3)C9—H90.9300
C1—C51.431 (3)C10—C111.314 (4)
C2—C31.416 (4)C10—H100.9300
C2—H20.9300C11—O21.368 (3)
C3—C41.323 (4)C11—H110.9300
C3—H30.9300C13—N31.461 (3)
C4—O11.364 (3)C13—H13A0.9700
C4—H40.9300C13—H13B0.9700
C5—N21.285 (2)N1—N21.393 (2)
C5—C61.498 (3)N3—H3A0.8600
C6—C71.531 (3)
N3—C12—N1115.41 (18)C8—C7—C6113.76 (18)
N3—C12—S1123.87 (16)N1—C7—H7108.8 (14)
N1—C12—S1120.71 (16)C8—C7—H7109.0 (14)
C13—C14—H14A109.5C6—C7—H7112.2 (14)
C13—C14—H14B109.5C9—C8—O2109.4 (2)
H14A—C14—H14B109.5C9—C8—C7134.2 (2)
C13—C14—H14C109.5O2—C8—C7116.44 (16)
H14A—C14—H14C109.5C8—C9—C10107.0 (2)
H14B—C14—H14C109.5C8—C9—H9126.5
C2—C1—O1109.9 (2)C10—C9—H9126.5
C2—C1—C5131.2 (2)C11—C10—C9106.7 (2)
O1—C1—C5118.87 (18)C11—C10—H10126.6
C1—C2—C3106.4 (3)C9—C10—H10126.6
C1—C2—H2126.8C10—C11—O2110.4 (2)
C3—C2—H2126.8C10—C11—H11124.8
C4—C3—C2106.9 (2)O2—C11—H11124.8
C4—C3—H3126.5C14—C13—N3112.3 (2)
C2—C3—H3126.5C14—C13—H13A109.1
C3—C4—O1110.3 (3)N3—C13—H13A109.1
C3—C4—H4124.8C14—C13—H13B109.1
O1—C4—H4124.8N3—C13—H13B109.1
N2—C5—C1122.78 (18)H13A—C13—H13B107.9
N2—C5—C6114.28 (17)C12—N1—N2120.34 (16)
C1—C5—C6122.92 (18)C12—N1—C7127.25 (16)
C5—C6—C7102.21 (16)N2—N1—C7112.40 (15)
C5—C6—H6A110.7 (15)C5—N2—N1107.46 (16)
C7—C6—H6A113.0 (15)C12—N3—C13122.8 (2)
C5—C6—H6B110.1 (14)C12—N3—H3A118.6
C7—C6—H6B112.3 (14)C13—N3—H3A118.6
H6A—C6—H6B108 (2)C1—O1—C4106.3 (2)
N1—C7—C8111.89 (16)C8—O2—C11106.43 (19)
N1—C7—C6100.83 (15)
O1—C1—C2—C30.3 (3)S1—C12—N1—N2177.30 (14)
C5—C1—C2—C3179.9 (2)N3—C12—N1—C7177.50 (18)
C1—C2—C3—C40.4 (4)S1—C12—N1—C72.8 (3)
C2—C3—C4—O10.4 (4)C8—C7—N1—C1274.8 (2)
C2—C1—C5—N2177.6 (3)C6—C7—N1—C12163.95 (19)
O1—C1—C5—N22.7 (3)C8—C7—N1—N2105.10 (19)
C2—C1—C5—C61.1 (4)C6—C7—N1—N216.2 (2)
O1—C1—C5—C6178.66 (19)C1—C5—N2—N1179.55 (17)
N2—C5—C6—C711.5 (2)C6—C5—N2—N11.7 (2)
C1—C5—C6—C7169.68 (18)C12—N1—N2—C5170.28 (17)
C5—C6—C7—N115.3 (2)C7—N1—N2—C59.8 (2)
C5—C6—C7—C8104.69 (19)N1—C12—N3—C13178.3 (2)
N1—C7—C8—C9109.5 (3)S1—C12—N3—C132.1 (3)
C6—C7—C8—C9137.0 (3)C14—C13—N3—C12161.1 (3)
N1—C7—C8—O269.9 (2)C2—C1—O1—C40.1 (3)
C6—C7—C8—O243.6 (2)C5—C1—O1—C4179.9 (2)
O2—C8—C9—C100.2 (3)C3—C4—O1—C10.2 (3)
C7—C8—C9—C10179.3 (2)C9—C8—O2—C110.0 (2)
C8—C9—C10—C110.2 (3)C7—C8—O2—C11179.50 (19)
C9—C10—C11—O20.2 (3)C10—C11—O2—C80.1 (3)
N3—C12—N1—N22.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cgi0.932.863.763 (3)165
Symmetry code: (i) x+1, y, z.
 

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