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In the title compound, C8H7N3O2S, the dihedral angle between the 1,2,4-triazole ring and the phenyl ring is 82.17 (14)°. The geometry around the S atom is distorted tetra­hedral. The mol­ecules are linked by inter­molecular C—H...N and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049646/at2166sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049646/at2166Isup2.hkl
Contains datablock I

CCDC reference: 629422

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.125
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Author Response: ...We have collected data on kappa IP diffractometer and processed using Denzo; and as we know that the DENZO image processing package is known to have problems with certain strong reflections. They are often excluded from the data set leading to a lower value for the above parameter.

0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON.

1-phenylsulfonyl-1H-1,2–4-triazole top
Crystal data top
C8H7N3O2SF(000) = 432
Mr = 209.23Dx = 1.513 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2728 reflections
a = 11.395 (14) Åθ = 3.8–25.0°
b = 5.045 (3) ŵ = 0.33 mm1
c = 17.698 (19) ÅT = 295 K
β = 115.445 (3)°Block, white
V = 918.7 (16) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
MacScience DIPLabo 32001
diffractometer
1284 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 3.8°
Detector resolution: 10.0 pixels mm-1h = 1313
ω scansk = 55
2728 measured reflectionsl = 2020
1535 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0688P)2 + 0.33P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1535 reflectionsΔρmax = 0.23 e Å3
128 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (5)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 F^2 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 F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
S60.25140 (6)0.51485 (11)0.52838 (4)0.0509 (2)
O70.37036 (18)0.6539 (4)0.55702 (12)0.0728 (7)
O80.13161 (17)0.6482 (3)0.50804 (11)0.0638 (6)
N10.26506 (16)0.3110 (4)0.60813 (11)0.0472 (6)
N20.38163 (18)0.2118 (5)0.66315 (12)0.0608 (7)
N40.2170 (2)0.0357 (5)0.68498 (14)0.0663 (8)
C30.3457 (3)0.0523 (6)0.70749 (17)0.0683 (10)
C50.1691 (2)0.1992 (5)0.62232 (14)0.0552 (8)
C90.2352 (2)0.2982 (4)0.44789 (13)0.0456 (7)
C100.1129 (2)0.2060 (5)0.39498 (14)0.0512 (7)
C110.1010 (3)0.0299 (5)0.33285 (16)0.0630 (9)
C120.2094 (3)0.0518 (6)0.32372 (18)0.0698 (10)
C130.3300 (3)0.0406 (6)0.37621 (18)0.0691 (10)
C140.3448 (2)0.2169 (5)0.43938 (15)0.0571 (8)
H30.405600.044300.752100.0820*
H50.081100.234100.591600.0660*
H100.039900.262100.401400.0610*
H110.019500.034200.296900.0760*
H120.200600.170800.281500.0840*
H130.402500.015700.369300.0830*
H140.426700.279400.475400.0690*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S60.0495 (4)0.0456 (4)0.0578 (4)0.0051 (2)0.0233 (3)0.0002 (2)
O70.0685 (12)0.0672 (12)0.0856 (13)0.0307 (9)0.0359 (10)0.0152 (9)
O80.0649 (11)0.0535 (10)0.0728 (11)0.0154 (8)0.0294 (9)0.0070 (8)
N10.0362 (10)0.0554 (11)0.0475 (10)0.0012 (8)0.0157 (8)0.0023 (8)
N20.0364 (11)0.0825 (14)0.0552 (12)0.0041 (9)0.0119 (9)0.0021 (10)
N40.0524 (13)0.0882 (16)0.0579 (13)0.0060 (11)0.0233 (10)0.0176 (11)
C30.0553 (16)0.091 (2)0.0520 (14)0.0121 (14)0.0168 (12)0.0151 (14)
C50.0398 (12)0.0713 (16)0.0545 (14)0.0006 (10)0.0203 (10)0.0069 (11)
C90.0439 (12)0.0458 (12)0.0485 (11)0.0017 (9)0.0213 (9)0.0063 (9)
C100.0410 (12)0.0577 (13)0.0547 (13)0.0007 (10)0.0205 (10)0.0034 (10)
C110.0563 (15)0.0729 (17)0.0544 (14)0.0085 (12)0.0187 (12)0.0053 (12)
C120.077 (2)0.0792 (18)0.0587 (16)0.0029 (15)0.0344 (14)0.0077 (13)
C130.0652 (17)0.0837 (19)0.0727 (18)0.0071 (14)0.0431 (15)0.0014 (14)
C140.0460 (13)0.0666 (15)0.0604 (14)0.0029 (11)0.0245 (11)0.0055 (11)
Geometric parameters (Å, º) top
S6—O71.413 (3)C10—C111.374 (4)
S6—O81.422 (3)C11—C121.376 (5)
S6—N11.699 (3)C12—C131.368 (5)
S6—C91.741 (3)C13—C141.381 (4)
N1—N21.361 (3)C3—H30.9293
N1—C51.346 (4)C5—H50.9293
N2—C31.307 (4)C10—H100.9307
N4—C31.347 (5)C11—H110.9296
N4—C51.299 (4)C12—H120.9297
C9—C101.383 (4)C13—H130.9300
C9—C141.383 (4)C14—H140.9303
O7···N22.883 (5)N4···H12vii2.5722
O7···C14i3.284 (5)C3···N2viii3.425 (6)
O8···C5ii3.296 (5)C5···O8ix3.355 (5)
O8···C5iii3.355 (5)C5···O8ii3.296 (5)
O8···C10iii3.406 (5)C10···O8ix3.406 (5)
O7···H14i2.6325C14···O7i3.284 (5)
O7···H142.6202C11···H11x3.0472
O8···H52.7594H3···N2viii2.5529
O8···H102.5987H5···O82.7594
O8···H5ii2.3800H5···O8ii2.3800
N1···N42.172 (4)H10···O82.5987
N2···O72.883 (5)H11···C11xi3.0472
N2···N42.254 (4)H11···N4vi2.8475
N2···C3iv3.425 (6)H12···N4xii2.5722
N4···N12.172 (4)H13···N2v2.9280
N2···H3iv2.5529H14···O72.6202
N2···H13v2.9280H14···O7i2.6325
N4···H11vi2.8475
O7—S6—O8121.63 (11)C11—C12—C13120.6 (3)
O7—S6—N1105.74 (11)C12—C13—C14120.4 (3)
O7—S6—C9110.69 (12)C9—C14—C13118.5 (2)
O8—S6—N1103.42 (11)N2—C3—H3121.87
O8—S6—C9109.69 (11)N4—C3—H3121.84
N1—S6—C9103.85 (10)N1—C5—H5124.76
S6—N1—N2122.01 (17)N4—C5—H5124.87
S6—N1—C5128.08 (17)C9—C10—H10120.56
N2—N1—C5109.50 (19)C11—C10—H10120.54
N1—N2—C3101.2 (2)C10—C11—H11119.91
C3—N4—C5102.6 (2)C12—C11—H11119.91
N2—C3—N4116.3 (3)C11—C12—H12119.70
N1—C5—N4110.4 (2)C13—C12—H12119.72
S6—C9—C10119.12 (19)C12—C13—H13119.77
S6—C9—C14119.47 (18)C14—C13—H13119.78
C10—C9—C14121.4 (2)C9—C14—H14120.79
C9—C10—C11118.9 (3)C13—C14—H14120.70
C10—C11—C12120.2 (3)
O7—S6—N1—N229.7 (2)C5—N1—N2—C31.5 (3)
O8—S6—N1—N2158.55 (18)N2—N1—C5—N41.3 (3)
C9—S6—N1—N286.9 (2)N1—N2—C3—N41.4 (3)
O7—S6—N1—C5158.5 (2)C3—N4—C5—N10.4 (3)
O8—S6—N1—C529.6 (2)C5—N4—C3—N20.6 (3)
C9—S6—N1—C585.0 (2)S6—C9—C10—C11178.39 (19)
O7—S6—C9—C10160.43 (18)S6—C9—C14—C13178.6 (2)
O8—S6—C9—C1023.5 (2)C10—C9—C14—C130.2 (4)
N1—S6—C9—C1086.51 (19)C14—C9—C10—C110.0 (4)
O7—S6—C9—C1421.1 (2)C9—C10—C11—C120.2 (4)
O8—S6—C9—C14158.06 (18)C10—C11—C12—C130.1 (4)
N1—S6—C9—C1491.9 (2)C11—C12—C13—C140.2 (5)
S6—N1—C5—N4173.99 (18)C12—C13—C14—C90.3 (4)
S6—N1—N2—C3174.74 (18)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x, y+1, z; (iv) x+1, y+1/2, z+3/2; (v) x+1, y, z+1; (vi) x, y, z+1; (vii) x, y1/2, z+1/2; (viii) x+1, y1/2, z+3/2; (ix) x, y1, z; (x) x, y+1/2, z+1/2; (xi) x, y1/2, z+1/2; (xii) x, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N2viii0.932.553.425 (6)157
C5—H5···O8ii0.932.383.296 (5)169
C12—H12···N4xii0.932.573.490 (6)169
Symmetry codes: (ii) x, y+1, z+1; (viii) x+1, y1/2, z+3/2; (xii) x, y1/2, z1/2.
 

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