Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804029423/hg6110sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804029423/hg61103sup2.hkl
Contains datablock 3

CCDC reference: 259594

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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-3H-1,2,4-triazole-3-thione top
Crystal data top
C13H11N3O2SF(000) = 568
Mr = 273.32Dx = 1.420 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 85 reflections
a = 7.0789 (6) Åθ = 6–20°
b = 8.4650 (6) ŵ = 0.25 mm1
c = 21.4774 (13) ÅT = 100 K
β = 96.492 (5)°Prism, colorless
V = 1278.74 (16) Å30.41 × 0.37 × 0.28 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3341 independent reflections
Radiation source: fine-focus sealed tube2719 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 9 pixels mm-1θmax = 29.0°, θmin = 3.7°
φ and ω–scans (per frame) rotations of 1.50° with an exposure time of 30 sec per frameh = 99
Absorption correction: numerical
(SADABS; Sheldrick, 2002)
k = 1111
Tmin = 0.903, Tmax = 0.932l = 2929
18096 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084All 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 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
S10.16971 (4)0.93785 (4)0.41382 (1)0.0121 (1)
O10.35582 (13)0.36922 (12)0.46204 (4)0.0148 (3)
O20.34249 (13)0.38946 (12)0.21407 (4)0.0160 (3)
N10.01166 (15)0.65064 (13)0.40833 (5)0.0101 (3)
N20.10488 (16)0.80567 (14)0.47701 (5)0.0124 (3)
N30.20761 (16)0.66924 (14)0.48175 (5)0.0131 (3)
C10.01672 (18)0.79914 (16)0.43362 (6)0.0108 (3)
C20.14822 (17)0.57650 (16)0.43928 (6)0.0111 (3)
C30.21487 (18)0.41649 (17)0.42725 (6)0.0120 (3)
C40.16875 (18)0.29740 (17)0.38952 (6)0.0136 (4)
C50.28876 (19)0.16702 (18)0.40107 (6)0.0158 (4)
C60.39803 (19)0.21631 (18)0.44476 (6)0.0163 (4)
C70.08525 (17)0.58565 (15)0.35886 (6)0.0100 (3)
C80.25797 (18)0.51102 (17)0.37357 (6)0.0138 (4)
C90.34847 (19)0.44268 (18)0.32569 (6)0.0144 (4)
C100.26341 (19)0.45080 (15)0.26415 (6)0.0118 (3)
C110.08792 (19)0.52541 (17)0.24988 (6)0.0137 (4)
C120.00083 (18)0.59422 (16)0.29737 (6)0.0125 (4)
C130.5320 (2)0.3294 (2)0.22556 (8)0.0256 (5)
H20.114 (3)0.882 (2)0.5039 (8)0.028 (5)*
H40.078 (3)0.300 (2)0.3625 (8)0.026 (5)*
H50.293 (2)0.060 (2)0.3820 (7)0.019 (4)*
H60.496 (2)0.169 (2)0.4654 (8)0.023 (4)*
H80.311 (2)0.5008 (18)0.4177 (7)0.011 (4)*
H90.464 (2)0.391 (2)0.3357 (7)0.019 (4)*
H110.031 (2)0.530 (2)0.2086 (8)0.022 (4)*
H120.118 (2)0.6451 (19)0.2883 (7)0.011 (4)*
H13A0.620 (3)0.411 (2)0.2441 (8)0.031 (5)*
H13B0.536 (3)0.236 (3)0.2538 (9)0.036 (5)*
H13C0.566 (3)0.302 (2)0.1850 (9)0.032 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0142 (2)0.0115 (2)0.0111 (2)0.0017 (1)0.0035 (1)0.0010 (1)
O10.0148 (5)0.0151 (5)0.0150 (4)0.0023 (4)0.0038 (4)0.0009 (4)
O20.0185 (5)0.0169 (5)0.0138 (4)0.0031 (4)0.0076 (4)0.0021 (4)
N10.0098 (5)0.0105 (6)0.0102 (5)0.0011 (4)0.0021 (4)0.0012 (4)
N20.0147 (5)0.0101 (6)0.0131 (5)0.0012 (5)0.0042 (4)0.0029 (4)
N30.0141 (5)0.0117 (6)0.0141 (5)0.0021 (4)0.0037 (4)0.0019 (4)
C10.0113 (6)0.0114 (7)0.0094 (5)0.0012 (5)0.0005 (4)0.0003 (5)
C20.0097 (5)0.0130 (7)0.0104 (5)0.0011 (5)0.0003 (4)0.0000 (5)
C30.0102 (5)0.0145 (7)0.0110 (5)0.0006 (5)0.0005 (4)0.0010 (5)
C40.0119 (6)0.0146 (7)0.0145 (6)0.0010 (5)0.0022 (5)0.0018 (5)
C50.0175 (7)0.0116 (7)0.0171 (6)0.0014 (5)0.0030 (5)0.0007 (5)
C60.0150 (6)0.0152 (7)0.0181 (6)0.0037 (6)0.0005 (5)0.0034 (5)
C70.0122 (6)0.0087 (6)0.0097 (5)0.0003 (5)0.0040 (4)0.0014 (5)
C80.0135 (6)0.0164 (7)0.0113 (6)0.0024 (5)0.0007 (5)0.0015 (5)
C90.0116 (6)0.0168 (7)0.0151 (6)0.0052 (6)0.0025 (5)0.0027 (5)
C100.0154 (6)0.0076 (6)0.0134 (6)0.0017 (5)0.0061 (5)0.0011 (5)
C110.0150 (6)0.0154 (7)0.0104 (6)0.0000 (5)0.0003 (5)0.0001 (5)
C120.0106 (6)0.0131 (7)0.0135 (6)0.0022 (5)0.0004 (5)0.0011 (5)
C130.0224 (8)0.0326 (10)0.0236 (8)0.0106 (7)0.0104 (6)0.0035 (7)
Geometric parameters (Å, º) top
S1—C11.6842 (14)C7—C121.3924 (18)
O1—C31.3721 (16)C7—C81.3808 (18)
O1—C61.3702 (18)C8—C91.3970 (19)
O2—C101.3697 (16)C9—C101.3908 (18)
O2—C131.4298 (17)C10—C111.3964 (19)
N1—C11.3751 (17)C11—C121.3854 (19)
N1—C21.3840 (17)C4—H40.91 (2)
N1—C71.4377 (17)C5—H50.993 (17)
N2—N31.3747 (17)C6—H60.953 (15)
N2—C11.3394 (17)C8—H80.983 (15)
N3—C21.3084 (17)C9—H90.931 (15)
N2—H20.874 (17)C11—H110.932 (17)
C2—C31.448 (2)C12—H120.935 (15)
C3—C41.3562 (19)C13—H13A0.984 (19)
C4—C51.431 (2)C13—H13B1.00 (2)
C5—C61.3480 (19)C13—H13C0.958 (19)
S1···N2i3.2658 (12)C13···C9x3.585 (2)
S1···C6ii3.5258 (14)C1···H2i3.058 (17)
S1···H13Ciii3.20 (2)C3···H9vi2.841 (15)
S1···H6iv3.172 (16)C4···H9vi2.836 (15)
S1···H11v2.949 (17)C5···H9vi2.841 (16)
S1···H2i2.400 (17)C6···H9vi2.848 (16)
O1···N32.7621 (16)C7···H42.685 (18)
O1···C8vi3.3691 (16)C8···H42.96 (2)
O1···C1ii3.4057 (16)C8···H13Ciii3.091 (18)
O2···C5v3.4011 (17)C9···H13B2.77 (2)
O1···H8vi2.684 (15)C9···H13A2.76 (2)
O1···H8ii2.792 (15)C10···H13Biii2.85 (2)
O1···H9vi2.871 (15)C10···H12vii2.960 (16)
O2···H5v2.510 (16)C12···H42.938 (17)
O2···H12vii2.606 (15)C13···H92.521 (15)
N1···N32.2204 (15)H2···S1i2.400 (17)
N2···N12.1339 (16)H2···C1i3.058 (17)
N2···S1i3.2658 (12)H2···H2i2.59 (3)
N2···C3ii3.4403 (18)H4···C72.685 (18)
N2···C4ii3.3875 (17)H4···C82.96 (2)
N3···O12.7621 (16)H4···C122.938 (17)
N3···N12.2204 (15)H5···O2vii2.510 (16)
N3···H6viii2.847 (15)H6···S1xi3.172 (16)
N3···H8ii2.762 (15)H6···N3viii2.847 (15)
C1···O1ii3.4057 (16)H8···O1ix2.684 (15)
C1···C6ii3.5400 (19)H8···O1ii2.792 (15)
C2···C2ii3.4126 (18)H8···N3ii2.762 (15)
C3···C9vi3.5829 (19)H9···O1ix2.871 (15)
C3···N2ii3.4403 (18)H9···C3ix2.841 (15)
C4···C123.4893 (19)H9···C4ix2.836 (15)
C4···C83.5702 (19)H9···C5ix2.841 (16)
C4···C73.1445 (19)H9···C6ix2.848 (16)
C4···N2ii3.3875 (17)H9···C132.521 (15)
C5···O2vii3.4011 (17)H9···H13A2.37 (2)
C6···C1ii3.5400 (19)H9···H13B2.30 (3)
C6···C9vi3.521 (2)H11···S1vii2.949 (17)
C6···S1ii3.5257 (14)H12···O2v2.606 (15)
C7···C43.1445 (19)H12···C10v2.960 (16)
C8···O1ix3.3691 (16)H13A···C92.76 (2)
C8···C43.5702 (19)H13A···H92.37 (2)
C9···C6ix3.521 (2)H13B···C92.77 (2)
C9···C3ix3.5829 (19)H13B···H92.30 (3)
C9···C13iii3.585 (2)H13B···C10x2.85 (2)
C10···C13iii3.514 (2)H13C···S1x3.20 (2)
C12···C43.4893 (19)H13C···C8x3.091 (18)
C13···C10x3.514 (2)
C3—O1—C6106.13 (10)O2—C10—C11115.57 (11)
C10—O2—C13117.26 (11)O2—C10—C9123.79 (12)
C1—N1—C2107.67 (11)C9—C10—C11120.65 (12)
C1—N1—C7125.53 (11)C10—C11—C12119.66 (12)
C2—N1—C7126.80 (11)C7—C12—C11119.35 (12)
N3—N2—C1113.82 (11)C3—C4—H4126.6 (11)
N2—N3—C2103.77 (10)C5—C4—H4127.1 (11)
N3—N2—H2119.5 (13)C4—C5—H5128.5 (9)
C1—N2—H2126.3 (13)C6—C5—H5125.2 (9)
N1—C1—N2103.64 (11)O1—C6—H6114.8 (10)
S1—C1—N1127.37 (10)C5—C6—H6134.4 (10)
S1—C1—N2128.99 (11)C7—C8—H8119.5 (9)
N1—C2—N3111.08 (12)C9—C8—H8121.1 (9)
N1—C2—C3124.73 (11)C8—C9—H9119.3 (9)
N3—C2—C3124.18 (12)C10—C9—H9121.2 (9)
O1—C3—C2114.71 (11)C10—C11—H11120.4 (9)
C2—C3—C4134.94 (12)C12—C11—H11120.0 (10)
O1—C3—C4110.34 (12)C7—C12—H12120.3 (9)
C3—C4—C5106.37 (12)C11—C12—H12120.4 (9)
C4—C5—C6106.29 (13)O2—C13—H13A111.0 (11)
O1—C6—C5110.87 (12)O2—C13—H13B110.4 (12)
C8—C7—C12121.47 (12)O2—C13—H13C104.9 (12)
N1—C7—C8119.35 (11)H13A—C13—H13B109.8 (16)
N1—C7—C12119.13 (11)H13A—C13—H13C109.0 (16)
C7—C8—C9119.27 (12)H13B—C13—H13C111.7 (16)
C8—C9—C10119.59 (12)
C6—O1—C3—C40.32 (14)N2—N3—C2—C3179.11 (12)
C3—O1—C6—C50.27 (14)N2—N3—C2—N10.10 (14)
C6—O1—C3—C2179.40 (11)N3—C2—C3—O13.28 (19)
C13—O2—C10—C97.00 (19)N3—C2—C3—C4175.50 (14)
C13—O2—C10—C11172.55 (12)N1—C2—C3—O1177.85 (11)
C1—N1—C2—C3178.53 (12)N1—C2—C3—C43.4 (2)
C1—N1—C2—N30.47 (15)O1—C3—C4—C50.25 (15)
C2—N1—C1—S1179.12 (10)C2—C3—C4—C5179.06 (14)
C2—N1—C7—C1284.51 (16)C3—C4—C5—C60.07 (15)
C7—N1—C2—C31.1 (2)C4—C5—C6—O10.13 (15)
C2—N1—C1—N20.82 (13)C12—C7—C8—C90.1 (2)
C7—N1—C1—N2179.51 (11)N1—C7—C12—C11177.07 (12)
C7—N1—C2—N3179.87 (12)N1—C7—C8—C9177.58 (12)
C7—N1—C1—S10.55 (19)C8—C7—C12—C110.5 (2)
C1—N1—C7—C1295.88 (15)C7—C8—C9—C100.0 (2)
C2—N1—C7—C893.08 (16)C8—C9—C10—O2179.00 (13)
C1—N1—C7—C886.53 (16)C8—C9—C10—C110.5 (2)
N3—N2—C1—S1179.00 (10)C9—C10—C11—C121.0 (2)
N3—N2—C1—N10.95 (14)O2—C10—C11—C12178.52 (12)
C1—N2—N3—C20.68 (14)C10—C11—C12—C71.0 (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) x1, y, z; (vii) x, y1/2, z+1/2; (viii) x1, y+1, z+1; (ix) x+1, y, z; (x) x+1, y1/2, z+1/2; (xi) x1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···S1i0.874 (17)2.400 (17)3.2658 (12)170.7 (17)
C5—H5···O2vii0.993 (17)2.510 (16)3.4011 (17)149.1 (12)
Symmetry codes: (i) x, y+2, z+1; (vii) x, y1/2, z+1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds