1-(N-Ethyl­thio­carbamo­yl)-3,5-di-2-fur­yl-2-pyrazoline

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.

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

No syntax errors found



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

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Computing details

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

Crystal data

C14H15N3O2S	F(000) = 608
Mr = 289.35	Dx = 1.330 Mg m^−3
Monoclinic, P21/c	Melting point = 408–409 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0192 (4) Å	Cell parameters from 9837 reflections
b = 22.1771 (10) Å	θ = 1.8–27.2°
c = 10.5972 (7) Å	µ = 0.23 mm^−1
β = 119.541 (4)°	T = 293 K
V = 1435.17 (14) Å^3	Prism, yellow
Z = 4	0.56 × 0.50 × 0.43 mm

Data collection

Stoe IPDS-2 diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	2420 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
ω scan rotation	h = −8→8
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −24→27
Tmin = 0.879, Tmax = 0.879	l = −13→13
13798 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1115P)^2 + 0.5302P] where P = (Fo^2 + 2Fc^2)/3
2808 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. In thin layer chromotography S-1, S-2 and S-4 solvent systems, R_f 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), C═N streching (1518^-1), C═C streching (1420^-1), pyrazoline C⁴—H streching (1390^-1), C═S 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; H_A,J_AB: 17.41 Hz, J_AX: 3.46 Hz), 3.45 p.p.m. (1H; dd; H_B,J_AB: 17.43 Hz, J_BX: 11.42 Hz), 6.10 p.p.m. (1H; dd; H_X,J_AX: 3.39 Hz, J_BX: 11.41 Hz), 1.25 p.p.m. (3H; t; CH₃,J_AB: 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,J_AB: 3.20 Hz), 6.47 p.p.m. (1H; m; 3-furan H³), 6.72 p.p.m. (1H; d; 3-furan H⁴, J_AB: 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 (Ų)

	x	y	z	Uiso*/Ueq
C12	0.1048 (3)	0.67841 (9)	0.8059 (2)	0.0563 (5)
C14	−0.2853 (5)	0.79673 (16)	0.6095 (3)	0.1063 (10)
H14A	−0.3788	0.8226	0.6276	0.159*
H14B	−0.3732	0.7688	0.5336	0.159*
H14C	−0.1994	0.8206	0.5804	0.159*
C1	0.4721 (3)	0.62884 (10)	0.5456 (2)	0.0603 (5)
C2	0.6292 (4)	0.59948 (14)	0.5337 (3)	0.0854 (7)
H2	0.7250	0.5708	0.5974	0.103*
C3	0.6206 (6)	0.62073 (17)	0.4049 (4)	0.1030 (10)
H3	0.7106	0.6088	0.3681	0.124*
C4	0.4603 (5)	0.66073 (16)	0.3472 (3)	0.0965 (9)
H4	0.4187	0.6816	0.2613	0.116*
C5	0.4059 (3)	0.62576 (9)	0.6533 (2)	0.0536 (4)
C6	0.5107 (3)	0.58420 (11)	0.7812 (2)	0.0607 (5)
C7	0.3563 (3)	0.58929 (9)	0.8441 (2)	0.0551 (5)
C8	0.2115 (3)	0.53632 (9)	0.8135 (2)	0.0549 (4)
C9	0.1471 (4)	0.50390 (11)	0.8920 (3)	0.0768 (6)
H9	0.1885	0.5099	0.9891	0.092*
C10	0.0036 (5)	0.45872 (11)	0.7995 (4)	0.0871 (8)
H10	−0.0674	0.4294	0.8240	0.104*
C11	−0.0096 (4)	0.46614 (12)	0.6724 (3)	0.0851 (7)
H11	−0.0930	0.4423	0.5913	0.102*
C13	−0.1435 (5)	0.76427 (14)	0.7385 (3)	0.0964 (9)
H13A	−0.2311	0.7409	0.7685	0.116*
H13B	−0.0572	0.7927	0.8153	0.116*
N1	0.2314 (3)	0.64411 (7)	0.76951 (18)	0.0573 (4)
N2	0.2540 (3)	0.65925 (7)	0.64996 (18)	0.0556 (4)
N3	0.0037 (3)	0.72381 (8)	0.7184 (2)	0.0701 (5)
H3A	0.0250	0.7299	0.6461	0.084*
O1	0.3645 (3)	0.66708 (8)	0.43141 (18)	0.0802 (5)
O2	0.1167 (3)	0.51387 (7)	0.67627 (16)	0.0700 (4)
S1	0.08539 (10)	0.66235 (3)	0.95363 (7)	0.0732 (2)
H6A	0.520 (4)	0.5444 (11)	0.751 (3)	0.072 (7)*
H6B	0.658 (4)	0.5979 (11)	0.849 (3)	0.076 (7)*
H7	0.429 (3)	0.5961 (9)	0.941 (2)	0.060 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C12	0.0535 (10)	0.0602 (11)	0.0604 (11)	−0.0059 (8)	0.0320 (9)	−0.0092 (9)
C14	0.109 (2)	0.122 (3)	0.109 (2)	0.051 (2)	0.0697 (19)	0.0250 (19)
C1	0.0563 (10)	0.0677 (12)	0.0637 (11)	−0.0046 (9)	0.0347 (9)	−0.0012 (9)
C2	0.0747 (15)	0.1003 (19)	0.1016 (19)	0.0132 (13)	0.0591 (15)	0.0071 (15)
C3	0.106 (2)	0.133 (3)	0.111 (2)	−0.003 (2)	0.085 (2)	−0.011 (2)
C4	0.105 (2)	0.133 (3)	0.0795 (17)	−0.0064 (19)	0.0669 (17)	0.0034 (16)
C5	0.0492 (9)	0.0562 (10)	0.0586 (10)	−0.0035 (8)	0.0290 (8)	−0.0004 (8)
C6	0.0491 (10)	0.0671 (13)	0.0671 (12)	0.0029 (9)	0.0294 (9)	0.0092 (10)
C7	0.0523 (10)	0.0621 (11)	0.0498 (10)	−0.0012 (8)	0.0243 (8)	0.0052 (8)
C8	0.0551 (10)	0.0552 (10)	0.0555 (10)	0.0039 (8)	0.0281 (8)	0.0086 (8)
C9	0.0925 (16)	0.0709 (14)	0.0777 (14)	−0.0014 (12)	0.0501 (13)	0.0175 (11)
C10	0.0962 (18)	0.0587 (13)	0.125 (2)	−0.0109 (12)	0.0689 (18)	0.0093 (14)
C11	0.0840 (16)	0.0677 (14)	0.106 (2)	−0.0227 (12)	0.0491 (15)	−0.0129 (14)
C13	0.100 (2)	0.104 (2)	0.0917 (18)	0.0385 (17)	0.0516 (16)	−0.0034 (16)
N1	0.0672 (10)	0.0550 (9)	0.0631 (9)	0.0045 (8)	0.0425 (8)	0.0072 (7)
N2	0.0628 (9)	0.0552 (9)	0.0597 (9)	0.0015 (7)	0.0386 (8)	0.0047 (7)
N3	0.0772 (11)	0.0722 (11)	0.0686 (11)	0.0178 (9)	0.0418 (9)	0.0008 (9)
O1	0.0847 (11)	0.1012 (12)	0.0716 (10)	0.0113 (9)	0.0515 (9)	0.0159 (9)
O2	0.0762 (9)	0.0689 (9)	0.0674 (9)	−0.0146 (7)	0.0373 (8)	−0.0060 (7)
S1	0.0769 (4)	0.0893 (4)	0.0702 (4)	−0.0088 (3)	0.0493 (3)	−0.0077 (3)

Geometric parameters (Å, º)

C12—N3	1.315 (3)	C6—H6A	0.95 (2)
C12—N1	1.362 (2)	C6—H6B	0.97 (2)
C12—S1	1.676 (2)	C7—N1	1.479 (3)
C14—C13	1.427 (4)	C7—C8	1.481 (3)
C14—H14A	0.9600	C7—H7	0.90 (2)
C14—H14B	0.9600	C8—C9	1.336 (3)
C14—H14C	0.9600	C8—O2	1.361 (2)
C1—C2	1.339 (3)	C9—C10	1.416 (4)
C1—O1	1.361 (3)	C9—H9	0.9300
C1—C5	1.431 (3)	C10—C11	1.314 (4)
C2—C3	1.416 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—O2	1.368 (3)
C3—C4	1.323 (4)	C11—H11	0.9300
C3—H3	0.9300	C13—N3	1.461 (3)
C4—O1	1.364 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—N2	1.285 (2)	N1—N2	1.393 (2)
C5—C6	1.498 (3)	N3—H3A	0.8600
C6—C7	1.531 (3)
N3—C12—N1	115.41 (18)	C8—C7—C6	113.76 (18)
N3—C12—S1	123.87 (16)	N1—C7—H7	108.8 (14)
N1—C12—S1	120.71 (16)	C8—C7—H7	109.0 (14)
C13—C14—H14A	109.5	C6—C7—H7	112.2 (14)
C13—C14—H14B	109.5	C9—C8—O2	109.4 (2)
H14A—C14—H14B	109.5	C9—C8—C7	134.2 (2)
C13—C14—H14C	109.5	O2—C8—C7	116.44 (16)
H14A—C14—H14C	109.5	C8—C9—C10	107.0 (2)
H14B—C14—H14C	109.5	C8—C9—H9	126.5
C2—C1—O1	109.9 (2)	C10—C9—H9	126.5
C2—C1—C5	131.2 (2)	C11—C10—C9	106.7 (2)
O1—C1—C5	118.87 (18)	C11—C10—H10	126.6
C1—C2—C3	106.4 (3)	C9—C10—H10	126.6
C1—C2—H2	126.8	C10—C11—O2	110.4 (2)
C3—C2—H2	126.8	C10—C11—H11	124.8
C4—C3—C2	106.9 (2)	O2—C11—H11	124.8
C4—C3—H3	126.5	C14—C13—N3	112.3 (2)
C2—C3—H3	126.5	C14—C13—H13A	109.1
C3—C4—O1	110.3 (3)	N3—C13—H13A	109.1
C3—C4—H4	124.8	C14—C13—H13B	109.1
O1—C4—H4	124.8	N3—C13—H13B	109.1
N2—C5—C1	122.78 (18)	H13A—C13—H13B	107.9
N2—C5—C6	114.28 (17)	C12—N1—N2	120.34 (16)
C1—C5—C6	122.92 (18)	C12—N1—C7	127.25 (16)
C5—C6—C7	102.21 (16)	N2—N1—C7	112.40 (15)
C5—C6—H6A	110.7 (15)	C5—N2—N1	107.46 (16)
C7—C6—H6A	113.0 (15)	C12—N3—C13	122.8 (2)
C5—C6—H6B	110.1 (14)	C12—N3—H3A	118.6
C7—C6—H6B	112.3 (14)	C13—N3—H3A	118.6
H6A—C6—H6B	108 (2)	C1—O1—C4	106.3 (2)
N1—C7—C8	111.89 (16)	C8—O2—C11	106.43 (19)
N1—C7—C6	100.83 (15)
O1—C1—C2—C3	0.3 (3)	S1—C12—N1—N2	−177.30 (14)
C5—C1—C2—C3	−179.9 (2)	N3—C12—N1—C7	−177.50 (18)
C1—C2—C3—C4	−0.4 (4)	S1—C12—N1—C7	2.8 (3)
C2—C3—C4—O1	0.4 (4)	C8—C7—N1—C12	74.8 (2)
C2—C1—C5—N2	177.6 (3)	C6—C7—N1—C12	−163.95 (19)
O1—C1—C5—N2	−2.7 (3)	C8—C7—N1—N2	−105.10 (19)
C2—C1—C5—C6	−1.1 (4)	C6—C7—N1—N2	16.2 (2)
O1—C1—C5—C6	178.66 (19)	C1—C5—N2—N1	179.55 (17)
N2—C5—C6—C7	11.5 (2)	C6—C5—N2—N1	−1.7 (2)
C1—C5—C6—C7	−169.68 (18)	C12—N1—N2—C5	170.28 (17)
C5—C6—C7—N1	−15.3 (2)	C7—N1—N2—C5	−9.8 (2)
C5—C6—C7—C8	104.69 (19)	N1—C12—N3—C13	178.3 (2)
N1—C7—C8—C9	−109.5 (3)	S1—C12—N3—C13	−2.1 (3)
C6—C7—C8—C9	137.0 (3)	C14—C13—N3—C12	−161.1 (3)
N1—C7—C8—O2	69.9 (2)	C2—C1—O1—C4	−0.1 (3)
C6—C7—C8—O2	−43.6 (2)	C5—C1—O1—C4	−179.9 (2)
O2—C8—C9—C10	−0.2 (3)	C3—C4—O1—C1	−0.2 (3)
C7—C8—C9—C10	179.3 (2)	C9—C8—O2—C11	0.0 (2)
C8—C9—C10—C11	0.2 (3)	C7—C8—O2—C11	−179.50 (19)
C9—C10—C11—O2	−0.2 (3)	C10—C11—O2—C8	0.1 (3)
N3—C12—N1—N2	2.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg^i	0.93	2.86	3.763 (3)	165

Symmetry code: (i) x+1, y, z.