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The title compound, C13H11N3O2S, has a non-planar conformation. The dihedral angles are 3.41 (8) and 85.48 (7)° between the triazole ring plane and the furan and benzene ring planes, respectively. The crystal packing is stabilized by several hydrogen bonds.
Supporting information
CCDC reference: 259594
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.084
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.27 Ratio
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
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
Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg et al., 2003); data reduction: EVALCCD; program(s) used to solve structure: SIR97 (Altomare, 1999); 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).
5-(2-Furyl)-4-(4-methoxyphenyl)-2,4-dihydro-3
H-1,2,4-triazole-3-thione
top
Crystal data top
C13H11N3O2S | F(000) = 568 |
Mr = 273.32 | Dx = 1.420 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 85 reflections |
a = 7.0789 (6) Å | θ = 6–20° |
b = 8.4650 (6) Å | µ = 0.25 mm−1 |
c = 21.4774 (13) Å | T = 100 K |
β = 96.492 (5)° | Prism, colorless |
V = 1278.74 (16) Å3 | 0.41 × 0.37 × 0.28 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 3341 independent reflections |
Radiation source: fine-focus sealed tube | 2719 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 9 pixels mm-1 | θmax = 29.0°, θmin = 3.7° |
φ and ω–scans (per frame) rotations of 1.50°
with an exposure time of 30 sec per frame | h = −9→9 |
Absorption correction: numerical (SADABS; Sheldrick, 2002) | k = −11→11 |
Tmin = 0.903, Tmax = 0.932 | l = −29→29 |
18096 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.4143P] where P = (Fo2 + 2Fc2)/3 |
3341 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | 0.16971 (4) | 0.93785 (4) | 0.41382 (1) | 0.0121 (1) | |
O1 | −0.35582 (13) | 0.36922 (12) | 0.46204 (4) | 0.0148 (3) | |
O2 | 0.34249 (13) | 0.38946 (12) | 0.21407 (4) | 0.0160 (3) | |
N1 | −0.01166 (15) | 0.65064 (13) | 0.40833 (5) | 0.0101 (3) | |
N2 | −0.10488 (16) | 0.80567 (14) | 0.47701 (5) | 0.0124 (3) | |
N3 | −0.20761 (16) | 0.66924 (14) | 0.48175 (5) | 0.0131 (3) | |
C1 | 0.01672 (18) | 0.79914 (16) | 0.43362 (6) | 0.0108 (3) | |
C2 | −0.14822 (17) | 0.57650 (16) | 0.43928 (6) | 0.0111 (3) | |
C3 | −0.21487 (18) | 0.41649 (17) | 0.42725 (6) | 0.0120 (3) | |
C4 | −0.16875 (18) | 0.29740 (17) | 0.38952 (6) | 0.0136 (4) | |
C5 | −0.28876 (19) | 0.16702 (18) | 0.40107 (6) | 0.0158 (4) | |
C6 | −0.39803 (19) | 0.21631 (18) | 0.44476 (6) | 0.0163 (4) | |
C7 | 0.08525 (17) | 0.58565 (15) | 0.35886 (6) | 0.0100 (3) | |
C8 | 0.25797 (18) | 0.51102 (17) | 0.37357 (6) | 0.0138 (4) | |
C9 | 0.34847 (19) | 0.44268 (18) | 0.32569 (6) | 0.0144 (4) | |
C10 | 0.26341 (19) | 0.45080 (15) | 0.26415 (6) | 0.0118 (3) | |
C11 | 0.08792 (19) | 0.52541 (17) | 0.24988 (6) | 0.0137 (4) | |
C12 | −0.00083 (18) | 0.59422 (16) | 0.29737 (6) | 0.0125 (4) | |
C13 | 0.5320 (2) | 0.3294 (2) | 0.22556 (8) | 0.0256 (5) | |
H2 | −0.114 (3) | 0.882 (2) | 0.5039 (8) | 0.028 (5)* | |
H4 | −0.078 (3) | 0.300 (2) | 0.3625 (8) | 0.026 (5)* | |
H5 | −0.293 (2) | 0.060 (2) | 0.3820 (7) | 0.019 (4)* | |
H6 | −0.496 (2) | 0.169 (2) | 0.4654 (8) | 0.023 (4)* | |
H8 | 0.311 (2) | 0.5008 (18) | 0.4177 (7) | 0.011 (4)* | |
H9 | 0.464 (2) | 0.391 (2) | 0.3357 (7) | 0.019 (4)* | |
H11 | 0.031 (2) | 0.530 (2) | 0.2086 (8) | 0.022 (4)* | |
H12 | −0.118 (2) | 0.6451 (19) | 0.2883 (7) | 0.011 (4)* | |
H13A | 0.620 (3) | 0.411 (2) | 0.2441 (8) | 0.031 (5)* | |
H13B | 0.536 (3) | 0.236 (3) | 0.2538 (9) | 0.036 (5)* | |
H13C | 0.566 (3) | 0.302 (2) | 0.1850 (9) | 0.032 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0142 (2) | 0.0115 (2) | 0.0111 (2) | −0.0017 (1) | 0.0035 (1) | −0.0010 (1) |
O1 | 0.0148 (5) | 0.0151 (5) | 0.0150 (4) | −0.0023 (4) | 0.0038 (4) | −0.0009 (4) |
O2 | 0.0185 (5) | 0.0169 (5) | 0.0138 (4) | 0.0031 (4) | 0.0076 (4) | −0.0021 (4) |
N1 | 0.0098 (5) | 0.0105 (6) | 0.0102 (5) | 0.0011 (4) | 0.0021 (4) | −0.0012 (4) |
N2 | 0.0147 (5) | 0.0101 (6) | 0.0131 (5) | −0.0012 (5) | 0.0042 (4) | −0.0029 (4) |
N3 | 0.0141 (5) | 0.0117 (6) | 0.0141 (5) | −0.0021 (4) | 0.0037 (4) | −0.0019 (4) |
C1 | 0.0113 (6) | 0.0114 (7) | 0.0094 (5) | 0.0012 (5) | 0.0005 (4) | 0.0003 (5) |
C2 | 0.0097 (5) | 0.0130 (7) | 0.0104 (5) | 0.0011 (5) | 0.0003 (4) | 0.0000 (5) |
C3 | 0.0102 (5) | 0.0145 (7) | 0.0110 (5) | 0.0006 (5) | 0.0005 (4) | 0.0010 (5) |
C4 | 0.0119 (6) | 0.0146 (7) | 0.0145 (6) | 0.0010 (5) | 0.0022 (5) | −0.0018 (5) |
C5 | 0.0175 (7) | 0.0116 (7) | 0.0171 (6) | 0.0014 (5) | −0.0030 (5) | −0.0007 (5) |
C6 | 0.0150 (6) | 0.0152 (7) | 0.0181 (6) | −0.0037 (6) | −0.0005 (5) | 0.0034 (5) |
C7 | 0.0122 (6) | 0.0087 (6) | 0.0097 (5) | 0.0003 (5) | 0.0040 (4) | −0.0014 (5) |
C8 | 0.0135 (6) | 0.0164 (7) | 0.0113 (6) | 0.0024 (5) | 0.0007 (5) | 0.0015 (5) |
C9 | 0.0116 (6) | 0.0168 (7) | 0.0151 (6) | 0.0052 (6) | 0.0025 (5) | 0.0027 (5) |
C10 | 0.0154 (6) | 0.0076 (6) | 0.0134 (6) | −0.0017 (5) | 0.0061 (5) | −0.0011 (5) |
C11 | 0.0150 (6) | 0.0154 (7) | 0.0104 (6) | 0.0000 (5) | −0.0003 (5) | −0.0001 (5) |
C12 | 0.0106 (6) | 0.0131 (7) | 0.0135 (6) | 0.0022 (5) | 0.0004 (5) | 0.0011 (5) |
C13 | 0.0224 (8) | 0.0326 (10) | 0.0236 (8) | 0.0106 (7) | 0.0104 (6) | −0.0035 (7) |
Geometric parameters (Å, º) top
S1—C1 | 1.6842 (14) | C7—C12 | 1.3924 (18) |
O1—C3 | 1.3721 (16) | C7—C8 | 1.3808 (18) |
O1—C6 | 1.3702 (18) | C8—C9 | 1.3970 (19) |
O2—C10 | 1.3697 (16) | C9—C10 | 1.3908 (18) |
O2—C13 | 1.4298 (17) | C10—C11 | 1.3964 (19) |
N1—C1 | 1.3751 (17) | C11—C12 | 1.3854 (19) |
N1—C2 | 1.3840 (17) | C4—H4 | 0.91 (2) |
N1—C7 | 1.4377 (17) | C5—H5 | 0.993 (17) |
N2—N3 | 1.3747 (17) | C6—H6 | 0.953 (15) |
N2—C1 | 1.3394 (17) | C8—H8 | 0.983 (15) |
N3—C2 | 1.3084 (17) | C9—H9 | 0.931 (15) |
N2—H2 | 0.874 (17) | C11—H11 | 0.932 (17) |
C2—C3 | 1.448 (2) | C12—H12 | 0.935 (15) |
C3—C4 | 1.3562 (19) | C13—H13A | 0.984 (19) |
C4—C5 | 1.431 (2) | C13—H13B | 1.00 (2) |
C5—C6 | 1.3480 (19) | C13—H13C | 0.958 (19) |
| | | |
S1···N2i | 3.2658 (12) | C13···C9x | 3.585 (2) |
S1···C6ii | 3.5258 (14) | C1···H2i | 3.058 (17) |
S1···H13Ciii | 3.20 (2) | C3···H9vi | 2.841 (15) |
S1···H6iv | 3.172 (16) | C4···H9vi | 2.836 (15) |
S1···H11v | 2.949 (17) | C5···H9vi | 2.841 (16) |
S1···H2i | 2.400 (17) | C6···H9vi | 2.848 (16) |
O1···N3 | 2.7621 (16) | C7···H4 | 2.685 (18) |
O1···C8vi | 3.3691 (16) | C8···H4 | 2.96 (2) |
O1···C1ii | 3.4057 (16) | C8···H13Ciii | 3.091 (18) |
O2···C5v | 3.4011 (17) | C9···H13B | 2.77 (2) |
O1···H8vi | 2.684 (15) | C9···H13A | 2.76 (2) |
O1···H8ii | 2.792 (15) | C10···H13Biii | 2.85 (2) |
O1···H9vi | 2.871 (15) | C10···H12vii | 2.960 (16) |
O2···H5v | 2.510 (16) | C12···H4 | 2.938 (17) |
O2···H12vii | 2.606 (15) | C13···H9 | 2.521 (15) |
N1···N3 | 2.2204 (15) | H2···S1i | 2.400 (17) |
N2···N1 | 2.1339 (16) | H2···C1i | 3.058 (17) |
N2···S1i | 3.2658 (12) | H2···H2i | 2.59 (3) |
N2···C3ii | 3.4403 (18) | H4···C7 | 2.685 (18) |
N2···C4ii | 3.3875 (17) | H4···C8 | 2.96 (2) |
N3···O1 | 2.7621 (16) | H4···C12 | 2.938 (17) |
N3···N1 | 2.2204 (15) | H5···O2vii | 2.510 (16) |
N3···H6viii | 2.847 (15) | H6···S1xi | 3.172 (16) |
N3···H8ii | 2.762 (15) | H6···N3viii | 2.847 (15) |
C1···O1ii | 3.4057 (16) | H8···O1ix | 2.684 (15) |
C1···C6ii | 3.5400 (19) | H8···O1ii | 2.792 (15) |
C2···C2ii | 3.4126 (18) | H8···N3ii | 2.762 (15) |
C3···C9vi | 3.5829 (19) | H9···O1ix | 2.871 (15) |
C3···N2ii | 3.4403 (18) | H9···C3ix | 2.841 (15) |
C4···C12 | 3.4893 (19) | H9···C4ix | 2.836 (15) |
C4···C8 | 3.5702 (19) | H9···C5ix | 2.841 (16) |
C4···C7 | 3.1445 (19) | H9···C6ix | 2.848 (16) |
C4···N2ii | 3.3875 (17) | H9···C13 | 2.521 (15) |
C5···O2vii | 3.4011 (17) | H9···H13A | 2.37 (2) |
C6···C1ii | 3.5400 (19) | H9···H13B | 2.30 (3) |
C6···C9vi | 3.521 (2) | H11···S1vii | 2.949 (17) |
C6···S1ii | 3.5257 (14) | H12···O2v | 2.606 (15) |
C7···C4 | 3.1445 (19) | H12···C10v | 2.960 (16) |
C8···O1ix | 3.3691 (16) | H13A···C9 | 2.76 (2) |
C8···C4 | 3.5702 (19) | H13A···H9 | 2.37 (2) |
C9···C6ix | 3.521 (2) | H13B···C9 | 2.77 (2) |
C9···C3ix | 3.5829 (19) | H13B···H9 | 2.30 (3) |
C9···C13iii | 3.585 (2) | H13B···C10x | 2.85 (2) |
C10···C13iii | 3.514 (2) | H13C···S1x | 3.20 (2) |
C12···C4 | 3.4893 (19) | H13C···C8x | 3.091 (18) |
C13···C10x | 3.514 (2) | | |
| | | |
C3—O1—C6 | 106.13 (10) | O2—C10—C11 | 115.57 (11) |
C10—O2—C13 | 117.26 (11) | O2—C10—C9 | 123.79 (12) |
C1—N1—C2 | 107.67 (11) | C9—C10—C11 | 120.65 (12) |
C1—N1—C7 | 125.53 (11) | C10—C11—C12 | 119.66 (12) |
C2—N1—C7 | 126.80 (11) | C7—C12—C11 | 119.35 (12) |
N3—N2—C1 | 113.82 (11) | C3—C4—H4 | 126.6 (11) |
N2—N3—C2 | 103.77 (10) | C5—C4—H4 | 127.1 (11) |
N3—N2—H2 | 119.5 (13) | C4—C5—H5 | 128.5 (9) |
C1—N2—H2 | 126.3 (13) | C6—C5—H5 | 125.2 (9) |
N1—C1—N2 | 103.64 (11) | O1—C6—H6 | 114.8 (10) |
S1—C1—N1 | 127.37 (10) | C5—C6—H6 | 134.4 (10) |
S1—C1—N2 | 128.99 (11) | C7—C8—H8 | 119.5 (9) |
N1—C2—N3 | 111.08 (12) | C9—C8—H8 | 121.1 (9) |
N1—C2—C3 | 124.73 (11) | C8—C9—H9 | 119.3 (9) |
N3—C2—C3 | 124.18 (12) | C10—C9—H9 | 121.2 (9) |
O1—C3—C2 | 114.71 (11) | C10—C11—H11 | 120.4 (9) |
C2—C3—C4 | 134.94 (12) | C12—C11—H11 | 120.0 (10) |
O1—C3—C4 | 110.34 (12) | C7—C12—H12 | 120.3 (9) |
C3—C4—C5 | 106.37 (12) | C11—C12—H12 | 120.4 (9) |
C4—C5—C6 | 106.29 (13) | O2—C13—H13A | 111.0 (11) |
O1—C6—C5 | 110.87 (12) | O2—C13—H13B | 110.4 (12) |
C8—C7—C12 | 121.47 (12) | O2—C13—H13C | 104.9 (12) |
N1—C7—C8 | 119.35 (11) | H13A—C13—H13B | 109.8 (16) |
N1—C7—C12 | 119.13 (11) | H13A—C13—H13C | 109.0 (16) |
C7—C8—C9 | 119.27 (12) | H13B—C13—H13C | 111.7 (16) |
C8—C9—C10 | 119.59 (12) | | |
| | | |
C6—O1—C3—C4 | −0.32 (14) | N2—N3—C2—C3 | 179.11 (12) |
C3—O1—C6—C5 | 0.27 (14) | N2—N3—C2—N1 | 0.10 (14) |
C6—O1—C3—C2 | −179.40 (11) | N3—C2—C3—O1 | 3.28 (19) |
C13—O2—C10—C9 | −7.00 (19) | N3—C2—C3—C4 | −175.50 (14) |
C13—O2—C10—C11 | 172.55 (12) | N1—C2—C3—O1 | −177.85 (11) |
C1—N1—C2—C3 | −178.53 (12) | N1—C2—C3—C4 | 3.4 (2) |
C1—N1—C2—N3 | 0.47 (15) | O1—C3—C4—C5 | 0.25 (15) |
C2—N1—C1—S1 | 179.12 (10) | C2—C3—C4—C5 | 179.06 (14) |
C2—N1—C7—C12 | 84.51 (16) | C3—C4—C5—C6 | −0.07 (15) |
C7—N1—C2—C3 | 1.1 (2) | C4—C5—C6—O1 | −0.13 (15) |
C2—N1—C1—N2 | −0.82 (13) | C12—C7—C8—C9 | 0.1 (2) |
C7—N1—C1—N2 | 179.51 (11) | N1—C7—C12—C11 | −177.07 (12) |
C7—N1—C2—N3 | −179.87 (12) | N1—C7—C8—C9 | 177.58 (12) |
C7—N1—C1—S1 | −0.55 (19) | C8—C7—C12—C11 | 0.5 (2) |
C1—N1—C7—C12 | −95.88 (15) | C7—C8—C9—C10 | 0.0 (2) |
C2—N1—C7—C8 | −93.08 (16) | C8—C9—C10—O2 | 179.00 (13) |
C1—N1—C7—C8 | 86.53 (16) | C8—C9—C10—C11 | −0.5 (2) |
N3—N2—C1—S1 | −179.00 (10) | C9—C10—C11—C12 | 1.0 (2) |
N3—N2—C1—N1 | 0.95 (14) | O2—C10—C11—C12 | −178.52 (12) |
C1—N2—N3—C2 | −0.68 (14) | C10—C11—C12—C7 | −1.0 (2) |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, y+1/2, −z+1/2; (iv) x+1, y+1, z; (v) −x, y+1/2, −z+1/2; (vi) x−1, y, z; (vii) −x, y−1/2, −z+1/2; (viii) −x−1, −y+1, −z+1; (ix) x+1, y, z; (x) −x+1, y−1/2, −z+1/2; (xi) x−1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···S1i | 0.874 (17) | 2.400 (17) | 3.2658 (12) | 170.7 (17) |
C5—H5···O2vii | 0.993 (17) | 2.510 (16) | 3.4011 (17) | 149.1 (12) |
Symmetry codes: (i) −x, −y+2, −z+1; (vii) −x, y−1/2, −z+1/2. |
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