In the title molecule, C
13H
11N
3OS, the triazole plane forms dihedral angles of 3.8 (2) and 81.3 (2)° with the furan and
p-tolyl ring planes, respectively. In the crystal structure, the molecules exist as centrosymmetric N—H
S hydrogen-bonded dimers, with an N
S distance of 3.312 (2) Å. The packing is further stabilized by C—H
O, C—H
N, C—H
π and π–π interactions.
Supporting information
CCDC reference: 248842
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.058
- wR factor = 0.110
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT480_ALERT_4_A Long H...A H-Bond Reported H3 .. CGP .. 2.96 Ang.
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H1 .. CGP .. 2.85 Ang.
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. O1 .. 2.75 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. N1 .. 2.69 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C1 .. CGP .. 3.66 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C3 .. CGP .. 3.71 Ang.
1 ALERT level A = In general: serious problem
1 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
0 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
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (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) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
5-Furan-2-yl-4-
p-tolyl-2,4-dihydro-1,2,4-triazole-3-thione
top
Crystal data top
C13H11N3OS | Z = 2 |
Mr = 257.31 | F(000) = 268 |
Triclinic, P1 | Dx = 1.332 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5665 (15) Å | Cell parameters from 7019 reflections |
b = 8.7759 (16) Å | θ = 2.1–27° |
c = 9.5372 (17) Å | µ = 0.24 mm−1 |
α = 91.796 (15)° | T = 293 K |
β = 91.407 (14)° | Prismatic, colorless |
γ = 116.386 (12)° | 0.31 × 0.20 × 0.07 mm |
V = 641.4 (2) Å3 | |
Data collection top
Stoe IPDS-2 diffractometer | 2518 independent reflections |
Radiation source: sealed X-ray tube | 1539 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.090 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
ω scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.937, Tmax = 0.987 | l = −11→11 |
8282 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0375P)2] where P = (Fo2 + 2Fc2)/3 |
2518 reflections | (Δ/σ)max = 0.020 |
164 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.25912 (11) | 0.55761 (10) | 0.63531 (11) | 0.0547 (3) | |
O1 | −0.2505 (3) | −0.2093 (3) | 0.6684 (3) | 0.0597 (6) | |
N1 | −0.1485 (3) | 0.1165 (3) | 0.5907 (3) | 0.0437 (6) | |
N2 | −0.0569 (3) | 0.2878 (3) | 0.5754 (3) | 0.0457 (7) | |
H2A | −0.0997 | 0.3466 | 0.5329 | 0.055* | |
N3 | 0.1163 (3) | 0.2180 (3) | 0.6889 (3) | 0.0394 (6) | |
C1 | −0.2665 (5) | −0.3612 (4) | 0.7120 (4) | 0.0589 (9) | |
H1 | −0.3680 | −0.4631 | 0.7021 | 0.071* | |
C2 | −0.1198 (5) | −0.3446 (4) | 0.7698 (4) | 0.0581 (9) | |
H2 | −0.0986 | −0.4307 | 0.8070 | 0.070* | |
C3 | 0.0010 (4) | −0.1705 (4) | 0.7652 (4) | 0.0568 (9) | |
H3 | 0.1166 | −0.1201 | 0.7989 | 0.068* | |
C4 | −0.0839 (4) | −0.0929 (4) | 0.7028 (3) | 0.0394 (7) | |
C5 | −0.0411 (3) | 0.0769 (3) | 0.6610 (3) | 0.0361 (7) | |
C6 | 0.1047 (4) | 0.3555 (3) | 0.6323 (3) | 0.0392 (7) | |
C7 | 0.2711 (3) | 0.2231 (3) | 0.7580 (3) | 0.0372 (7) | |
C8 | 0.3083 (4) | 0.2737 (4) | 0.8975 (3) | 0.0519 (8) | |
H8 | 0.2367 | 0.3082 | 0.9473 | 0.062* | |
C9 | 0.4530 (5) | 0.2726 (4) | 0.9624 (4) | 0.0591 (9) | |
H9 | 0.4781 | 0.3068 | 1.0569 | 0.071* | |
C10 | 0.5618 (4) | 0.2224 (4) | 0.8915 (4) | 0.0517 (9) | |
C11 | 0.5207 (4) | 0.1729 (4) | 0.7511 (4) | 0.0538 (9) | |
H11 | 0.5916 | 0.1375 | 0.7011 | 0.065* | |
C12 | 0.3779 (4) | 0.1746 (4) | 0.6835 (3) | 0.0454 (8) | |
H12 | 0.3539 | 0.1432 | 0.5884 | 0.054* | |
C13 | 0.7184 (5) | 0.2198 (5) | 0.9643 (4) | 0.0783 (13) | |
H13A | 0.7442 | 0.2851 | 1.0518 | 0.117* | |
H13B | 0.8167 | 0.2683 | 0.9058 | 0.117* | |
H13C | 0.6941 | 0.1044 | 0.9818 | 0.117* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0471 (5) | 0.0372 (4) | 0.0757 (7) | 0.0159 (4) | −0.0154 (4) | 0.0039 (4) |
O1 | 0.0479 (14) | 0.0443 (13) | 0.0764 (17) | 0.0111 (11) | −0.0105 (12) | 0.0130 (11) |
N1 | 0.0356 (14) | 0.0407 (14) | 0.0543 (17) | 0.0167 (12) | −0.0037 (12) | 0.0041 (12) |
N2 | 0.0395 (14) | 0.0392 (14) | 0.0617 (18) | 0.0205 (12) | −0.0061 (12) | 0.0075 (12) |
N3 | 0.0343 (13) | 0.0387 (13) | 0.0467 (16) | 0.0177 (11) | −0.0021 (11) | 0.0037 (11) |
C1 | 0.057 (2) | 0.0377 (18) | 0.072 (3) | 0.0120 (16) | 0.0042 (18) | 0.0121 (16) |
C2 | 0.061 (2) | 0.0464 (19) | 0.071 (3) | 0.0263 (17) | 0.0072 (18) | 0.0161 (17) |
C3 | 0.0430 (19) | 0.0470 (19) | 0.078 (3) | 0.0173 (16) | −0.0062 (17) | 0.0159 (17) |
C4 | 0.0336 (16) | 0.0426 (17) | 0.0394 (18) | 0.0147 (14) | 0.0012 (13) | 0.0025 (13) |
C5 | 0.0324 (16) | 0.0403 (16) | 0.0369 (17) | 0.0174 (14) | −0.0001 (13) | 0.0035 (13) |
C6 | 0.0438 (17) | 0.0382 (16) | 0.0411 (19) | 0.0234 (14) | −0.0008 (14) | 0.0009 (13) |
C7 | 0.0321 (15) | 0.0354 (15) | 0.0428 (19) | 0.0139 (12) | −0.0028 (13) | 0.0053 (13) |
C8 | 0.061 (2) | 0.062 (2) | 0.045 (2) | 0.0391 (18) | −0.0004 (16) | −0.0034 (16) |
C9 | 0.066 (2) | 0.066 (2) | 0.045 (2) | 0.0302 (19) | −0.0148 (18) | −0.0022 (17) |
C10 | 0.0446 (19) | 0.0435 (17) | 0.065 (2) | 0.0182 (15) | −0.0119 (17) | 0.0119 (16) |
C11 | 0.0400 (18) | 0.063 (2) | 0.065 (3) | 0.0288 (17) | −0.0024 (16) | 0.0011 (18) |
C12 | 0.0422 (18) | 0.0550 (19) | 0.0402 (19) | 0.0232 (15) | −0.0003 (14) | −0.0028 (15) |
C13 | 0.057 (2) | 0.086 (3) | 0.092 (3) | 0.033 (2) | −0.025 (2) | 0.018 (2) |
Geometric parameters (Å, º) top
S1—C6 | 1.675 (3) | C6—N3 | 1.380 (3) |
O1—C4 | 1.360 (3) | C7—C12 | 1.372 (4) |
N1—C5 | 1.298 (3) | C8—C7 | 1.372 (4) |
N2—C6 | 1.332 (4) | C8—H8 | 0.93 |
N2—N1 | 1.366 (3) | C9—C8 | 1.376 (4) |
N2—H2A | 0.86 | C9—C10 | 1.378 (5) |
N3—C7 | 1.448 (3) | C9—H9 | 0.93 |
C1—C2 | 1.305 (5) | C10—C11 | 1.382 (5) |
C1—O1 | 1.358 (4) | C11—C12 | 1.376 (4) |
C1—H1 | 0.93 | C11—H11 | 0.93 |
C2—C3 | 1.417 (4) | C12—H12 | 0.93 |
C2—H2 | 0.93 | C13—C10 | 1.505 (4) |
C3—H3 | 0.93 | C13—H13A | 0.96 |
C4—C3 | 1.338 (4) | C13—H13B | 0.96 |
C4—C5 | 1.440 (4) | C13—H13C | 0.96 |
C5—N3 | 1.378 (4) | | |
| | | |
C1—O1—C4 | 106.5 (2) | N3—C6—S1 | 127.6 (2) |
C5—N1—N2 | 104.1 (2) | C12—C7—C8 | 120.7 (3) |
C6—N2—N1 | 114.0 (2) | C12—C7—N3 | 119.4 (3) |
C6—N2—H2A | 123.0 | C8—C7—N3 | 119.9 (3) |
N1—N2—H2A | 123.0 | C7—C8—C9 | 119.1 (3) |
C5—N3—C6 | 107.6 (2) | C7—C8—H8 | 120.5 |
C5—N3—C7 | 127.2 (2) | C9—C8—H8 | 120.5 |
C6—N3—C7 | 125.0 (2) | C8—C9—C10 | 121.9 (3) |
C2—C1—O1 | 110.7 (3) | C8—C9—H9 | 119.0 |
C2—C1—H1 | 124.6 | C10—C9—H9 | 119.0 |
O1—C1—H1 | 124.6 | C9—C10—C11 | 117.4 (3) |
C1—C2—C3 | 107.0 (3) | C9—C10—C13 | 121.3 (3) |
C1—C2—H2 | 126.5 | C11—C10—C13 | 121.2 (3) |
C3—C2—H2 | 126.5 | C12—C11—C10 | 121.7 (3) |
C4—C3—C2 | 106.5 (3) | C12—C11—H11 | 119.1 |
C4—C3—H3 | 126.8 | C10—C11—H11 | 119.1 |
C2—C3—H3 | 126.8 | C7—C12—C11 | 119.2 (3) |
C3—C4—O1 | 109.3 (3) | C7—C12—H12 | 120.4 |
C3—C4—C5 | 136.2 (3) | C11—C12—H12 | 120.4 |
O1—C4—C5 | 114.5 (2) | C10—C13—H13A | 109.5 |
N1—C5—N3 | 111.0 (2) | C10—C13—H13B | 109.5 |
N1—C5—C4 | 123.6 (3) | H13A—C13—H13B | 109.5 |
N3—C5—C4 | 125.5 (2) | C10—C13—H13C | 109.5 |
N2—C6—N3 | 103.2 (2) | H13A—C13—H13C | 109.5 |
N2—C6—S1 | 129.2 (2) | H13B—C13—H13C | 109.5 |
| | | |
C10—C9—C8—C7 | 0.1 (5) | N1—C5—N3—C6 | 0.5 (3) |
C2—C1—O1—C4 | −0.5 (4) | C4—C5—N3—C6 | −179.6 (3) |
O1—C1—C2—C3 | 0.4 (4) | N1—C5—N3—C7 | −176.4 (3) |
C8—C9—C10—C11 | 0.2 (5) | C4—C5—N3—C7 | 3.5 (5) |
C8—C9—C10—C13 | −179.2 (3) | N2—C6—N3—C5 | 0.1 (3) |
C1—O1—C4—C3 | 0.3 (4) | S1—C6—N3—C5 | −179.7 (2) |
C1—O1—C4—C5 | 178.5 (3) | N2—C6—N3—C7 | 177.0 (3) |
O1—C4—C3—C2 | −0.1 (4) | S1—C6—N3—C7 | −2.8 (4) |
C5—C4—C3—C2 | −177.7 (3) | C9—C8—C7—C12 | −1.0 (5) |
C1—C2—C3—C4 | −0.2 (4) | C9—C8—C7—N3 | 178.0 (3) |
N1—N2—C6—N3 | −0.6 (3) | C5—N3—C7—C12 | 79.3 (4) |
N1—N2—C6—S1 | 179.2 (2) | C6—N3—C7—C12 | −97.1 (3) |
C6—N2—N1—C5 | 0.9 (3) | C5—N3—C7—C8 | −99.7 (4) |
N2—N1—C5—N3 | −0.8 (3) | C6—N3—C7—C8 | 83.9 (4) |
N2—N1—C5—C4 | 179.3 (3) | C9—C10—C11—C12 | 0.5 (5) |
C3—C4—C5—N1 | 174.6 (4) | C13—C10—C11—C12 | 179.9 (3) |
O1—C4—C5—N1 | −3.0 (4) | C8—C7—C12—C11 | 1.7 (4) |
C3—C4—C5—N3 | −5.3 (6) | N3—C7—C12—C11 | −177.3 (3) |
O1—C4—C5—N3 | 177.1 (3) | C10—C11—C12—C7 | −1.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···S1i | 0.86 | 2.48 | 3.312 (2) | 164 |
C11—H11···N1ii | 0.93 | 2.56 | 3.468 (4) | 165 |
C12—H12···O1iii | 0.93 | 2.75 | 3.567 (4) | 147 |
C12—H12···N1iii | 0.93 | 2.69 | 3.477 (4) | 143 |
C1—H1···CgPiv | 0.93 | 2.85 | 3.663 (4) | 146 |
C3—H3···CgP | 0.93 | 2.96 | 3.706 (4) | 138 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z; (iii) −x, −y, −z+1; (iv) x−1, y−1, z. |