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In the title compound, C16H14N4O3S, the electron delocalization in the triazole ring is reflected in the C-N bond lengths.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051543/hk2168sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051543/hk2168Isup2.hkl
Contains datablock I

CCDC reference: 633885

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.092
  • wR factor = 0.227
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C9 .. 8.30 su
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.32 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C8 .. 5.26 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick,1997); program(s) used to refine structure: SHELXL97 (Sheldrick,1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

5-(4-Methoxyphenyl)-3-(4-nitrobenzylsulfanyl)-4,5-dihydro-3H-1,2,4-triazole top
Crystal data top
C16H14N4O3SZ = 2
Mr = 342.38F(000) = 356
Triclinic, P1Dx = 1.456 Mg m3
Hall symbol: -P 1Melting point: 432(1) K
a = 8.0207 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.1947 (18) ÅCell parameters from 1520 reflections
c = 12.536 (3) Åθ = 2.7–24.9°
α = 93.926 (4)°µ = 0.23 mm1
β = 91.031 (4)°T = 298 K
γ = 108.050 (4)°Block, colorless
V = 780.9 (3) Å30.34 × 0.15 × 0.14 mm
Data collection top
Bruker APEX area-detector
diffractometer
2740 independent reflections
Radiation source: fine-focus sealed tube2355 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.948, Tmax = 0.959k = 99
4154 measured reflectionsl = 1410
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)] = 0.092Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0894P)2 + 1.1058P]
where P = (Fo2 + 2Fc2)/3
2740 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.54 e Å3
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
xyzUiso*/Ueq
S10.29274 (18)0.70340 (17)0.66533 (10)0.0618 (5)
O10.0172 (5)0.2411 (5)0.2066 (3)0.0774 (12)
O20.2948 (6)1.4558 (5)0.9733 (4)0.0852 (13)
O30.1655 (7)1.2833 (6)1.0875 (4)0.1056 (17)
N10.2369 (4)0.4157 (4)0.5425 (2)0.0314 (7)
H10.14970.43100.50830.038*
N20.4600 (5)0.4591 (5)0.6565 (3)0.0559 (10)
N30.4359 (5)0.3019 (5)0.5936 (3)0.0557 (10)
N40.2500 (6)1.3139 (5)1.0082 (4)0.0603 (11)
C10.0756 (8)0.3877 (7)0.1941 (6)0.0842 (19)
H1A0.20100.35130.19030.126*
H1B0.02340.45530.12950.126*
H1C0.04190.45580.25410.126*
C20.0865 (6)0.1217 (6)0.2895 (4)0.0536 (12)
C30.1970 (6)0.1419 (6)0.3710 (4)0.0552 (12)
H30.22530.24350.37270.066*
C40.2637 (6)0.0103 (6)0.4489 (4)0.0539 (12)
H40.33650.02430.50370.065*
C50.2248 (6)0.1434 (6)0.4477 (3)0.0450 (10)
C60.1120 (6)0.1602 (6)0.3668 (4)0.0537 (12)
H60.08240.26110.36550.064*
C70.0440 (7)0.0292 (7)0.2889 (4)0.0610 (13)
H70.03140.04200.23520.073*
C80.3046 (6)0.2836 (6)0.5294 (3)0.0451 (10)
C90.3404 (6)0.5165 (6)0.6222 (4)0.0465 (11)
C100.4321 (7)0.7656 (6)0.7858 (4)0.0551 (12)
H10A0.41280.66880.82960.066*
H10B0.55460.80340.76790.066*
C110.3851 (6)0.9106 (6)0.8455 (4)0.0468 (11)
C120.4359 (6)1.0741 (6)0.8098 (4)0.0534 (12)
H120.50051.09450.74850.064*
C130.3933 (6)1.2061 (6)0.8622 (4)0.0528 (12)
H130.42781.31540.83720.063*
C140.2980 (6)1.1740 (6)0.9531 (4)0.0468 (11)
C150.2440 (6)1.0123 (6)0.9902 (4)0.0490 (11)
H150.17910.99211.05140.059*
C160.2873 (6)0.8818 (5)0.9358 (4)0.0477 (11)
H160.25040.77190.95990.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0728 (9)0.0599 (8)0.0603 (8)0.0341 (6)0.0075 (6)0.0040 (6)
O10.080 (3)0.062 (2)0.093 (3)0.033 (2)0.011 (2)0.023 (2)
O20.111 (3)0.043 (2)0.105 (3)0.030 (2)0.008 (3)0.000 (2)
O30.154 (5)0.074 (3)0.107 (4)0.060 (3)0.061 (4)0.008 (3)
N10.0293 (16)0.0357 (17)0.0325 (16)0.0158 (14)0.0042 (13)0.0002 (13)
N20.063 (3)0.057 (2)0.053 (2)0.027 (2)0.003 (2)0.0004 (19)
N30.065 (3)0.060 (3)0.051 (2)0.033 (2)0.003 (2)0.0016 (19)
N40.070 (3)0.049 (3)0.064 (3)0.024 (2)0.003 (2)0.006 (2)
C10.077 (4)0.053 (3)0.120 (5)0.022 (3)0.007 (4)0.025 (3)
C20.049 (3)0.051 (3)0.060 (3)0.016 (2)0.012 (2)0.003 (2)
C30.059 (3)0.039 (3)0.073 (3)0.022 (2)0.008 (3)0.012 (2)
C40.064 (3)0.053 (3)0.053 (3)0.026 (2)0.005 (2)0.019 (2)
C50.044 (2)0.051 (3)0.044 (2)0.019 (2)0.0082 (19)0.008 (2)
C60.054 (3)0.052 (3)0.063 (3)0.029 (2)0.001 (2)0.003 (2)
C70.063 (3)0.062 (3)0.064 (3)0.032 (3)0.011 (3)0.007 (3)
C80.052 (3)0.049 (3)0.039 (2)0.021 (2)0.009 (2)0.0101 (19)
C90.049 (3)0.049 (3)0.046 (3)0.021 (2)0.010 (2)0.010 (2)
C100.061 (3)0.057 (3)0.054 (3)0.030 (2)0.004 (2)0.007 (2)
C110.043 (2)0.049 (3)0.048 (3)0.014 (2)0.008 (2)0.002 (2)
C120.056 (3)0.056 (3)0.051 (3)0.020 (2)0.009 (2)0.010 (2)
C130.060 (3)0.039 (2)0.059 (3)0.014 (2)0.002 (2)0.010 (2)
C140.050 (3)0.043 (2)0.048 (3)0.017 (2)0.005 (2)0.001 (2)
C150.053 (3)0.049 (3)0.046 (2)0.017 (2)0.005 (2)0.003 (2)
C160.054 (3)0.036 (2)0.052 (3)0.011 (2)0.001 (2)0.008 (2)
Geometric parameters (Å, º) top
S1—C91.744 (5)C4—C51.389 (6)
S1—C101.809 (5)C4—H40.9300
O1—C21.360 (6)C5—C61.389 (6)
O1—C11.419 (6)C5—C81.462 (6)
O2—N41.221 (5)C6—C71.370 (7)
O3—N41.209 (6)C6—H60.9300
N1—C91.343 (5)C7—H70.9300
N1—C81.355 (5)C10—C111.510 (6)
N1—H10.8600C10—H10A0.9700
N2—C91.272 (6)C10—H10B0.9700
N2—N31.421 (6)C11—C161.380 (6)
N3—C81.279 (6)C11—C121.383 (6)
N4—C141.454 (6)C12—C131.363 (6)
C1—H1A0.9600C12—H120.9300
C1—H1B0.9600C13—C141.378 (7)
C1—H1C0.9600C13—H130.9300
C2—C71.381 (7)C14—C151.377 (6)
C2—C31.393 (7)C15—C161.367 (6)
C3—C41.372 (7)C15—H150.9300
C3—H30.9300C16—H160.9300
C9—S1—C1099.5 (2)C6—C7—H7119.7
C2—O1—C1118.6 (5)C2—C7—H7119.7
C9—N1—C8102.4 (3)N3—C8—N1112.5 (4)
C9—N1—H1128.8N3—C8—C5128.5 (4)
C8—N1—H1128.8N1—C8—C5119.0 (4)
C9—N2—N3104.9 (4)N2—C9—N1114.1 (4)
C8—N3—N2106.1 (4)N2—C9—S1129.1 (4)
O3—N4—O2122.7 (5)N1—C9—S1116.8 (3)
O3—N4—C14117.8 (4)C11—C10—S1107.2 (3)
O2—N4—C14119.5 (5)C11—C10—H10A110.3
O1—C1—H1A109.5S1—C10—H10A110.3
O1—C1—H1B109.5C11—C10—H10B110.3
H1A—C1—H1B109.5S1—C10—H10B110.3
O1—C1—H1C109.5H10A—C10—H10B108.5
H1A—C1—H1C109.5C16—C11—C12118.6 (4)
H1B—C1—H1C109.5C16—C11—C10120.6 (4)
O1—C2—C7116.0 (5)C12—C11—C10120.8 (4)
O1—C2—C3124.4 (5)C13—C12—C11121.5 (5)
C7—C2—C3119.7 (5)C13—C12—H12119.2
C4—C3—C2119.3 (4)C11—C12—H12119.2
C4—C3—H3120.4C12—C13—C14118.6 (4)
C2—C3—H3120.4C12—C13—H13120.7
C3—C4—C5121.5 (4)C14—C13—H13120.7
C3—C4—H4119.3C15—C14—C13121.3 (4)
C5—C4—H4119.3C15—C14—N4120.0 (4)
C6—C5—C4118.4 (4)C13—C14—N4118.6 (4)
C6—C5—C8121.7 (4)C16—C15—C14119.0 (4)
C4—C5—C8119.9 (4)C16—C15—H15120.5
C7—C6—C5120.5 (4)C14—C15—H15120.5
C7—C6—H6119.7C15—C16—C11121.0 (4)
C5—C6—H6119.7C15—C16—H16119.5
C6—C7—C2120.6 (5)C11—C16—H16119.5
C9—N2—N3—C80.1 (5)N3—N2—C9—S1179.1 (3)
C1—O1—C2—C7171.1 (5)C8—N1—C9—N20.3 (5)
C1—O1—C2—C37.7 (8)C8—N1—C9—S1179.0 (3)
O1—C2—C3—C4178.0 (5)C10—S1—C9—N210.3 (5)
C7—C2—C3—C40.8 (7)C10—S1—C9—N1168.8 (3)
C2—C3—C4—C50.7 (7)C9—S1—C10—C11170.4 (3)
C3—C4—C5—C61.7 (7)S1—C10—C11—C16104.8 (4)
C3—C4—C5—C8177.3 (4)S1—C10—C11—C1273.8 (5)
C4—C5—C6—C71.4 (7)C16—C11—C12—C130.8 (7)
C8—C5—C6—C7177.6 (4)C10—C11—C12—C13179.5 (4)
C5—C6—C7—C20.0 (8)C11—C12—C13—C140.2 (7)
O1—C2—C7—C6177.7 (5)C12—C13—C14—C150.8 (7)
C3—C2—C7—C61.1 (8)C12—C13—C14—N4179.0 (4)
N2—N3—C8—N10.3 (5)O3—N4—C14—C151.4 (7)
N2—N3—C8—C5179.9 (4)O2—N4—C14—C15178.2 (4)
C9—N1—C8—N30.3 (5)O3—N4—C14—C13179.6 (5)
C9—N1—C8—C5179.9 (4)O2—N4—C14—C130.0 (7)
C6—C5—C8—N3163.8 (5)C13—C14—C15—C160.4 (7)
C4—C5—C8—N315.1 (7)N4—C14—C15—C16178.6 (4)
C6—C5—C8—N115.9 (6)C14—C15—C16—C110.7 (7)
C4—C5—C8—N1165.1 (4)C12—C11—C16—C151.3 (7)
N3—N2—C9—N10.1 (5)C10—C11—C16—C15179.9 (4)
 

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