In the title compound, C
8H
7N
3O
2S, 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
CCDC reference: 629422
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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-1
H-1,2–4-triazole
top
Crystal data top
C8H7N3O2S | F(000) = 432 |
Mr = 209.23 | Dx = 1.513 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2728 reflections |
a = 11.395 (14) Å | θ = 3.8–25.0° |
b = 5.045 (3) Å | µ = 0.33 mm−1 |
c = 17.698 (19) Å | T = 295 K |
β = 115.445 (3)° | Block, white |
V = 918.7 (16) Å3 | 0.25 × 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 tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 3.8° |
Detector resolution: 10.0 pixels mm-1 | h = −13→13 |
ω scans | k = −5→5 |
2728 measured reflections | l = −20→20 |
1535 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-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 reflections | Δρmax = 0.23 e Å−3 |
128 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S6 | 0.25140 (6) | 0.51485 (11) | 0.52838 (4) | 0.0509 (2) | |
O7 | 0.37036 (18) | 0.6539 (4) | 0.55702 (12) | 0.0728 (7) | |
O8 | 0.13161 (17) | 0.6482 (3) | 0.50804 (11) | 0.0638 (6) | |
N1 | 0.26506 (16) | 0.3110 (4) | 0.60813 (11) | 0.0472 (6) | |
N2 | 0.38163 (18) | 0.2118 (5) | 0.66315 (12) | 0.0608 (7) | |
N4 | 0.2170 (2) | 0.0357 (5) | 0.68498 (14) | 0.0663 (8) | |
C3 | 0.3457 (3) | 0.0523 (6) | 0.70749 (17) | 0.0683 (10) | |
C5 | 0.1691 (2) | 0.1992 (5) | 0.62232 (14) | 0.0552 (8) | |
C9 | 0.2352 (2) | 0.2982 (4) | 0.44789 (13) | 0.0456 (7) | |
C10 | 0.1129 (2) | 0.2060 (5) | 0.39498 (14) | 0.0512 (7) | |
C11 | 0.1010 (3) | 0.0299 (5) | 0.33285 (16) | 0.0630 (9) | |
C12 | 0.2094 (3) | −0.0518 (6) | 0.32372 (18) | 0.0698 (10) | |
C13 | 0.3300 (3) | 0.0406 (6) | 0.37621 (18) | 0.0691 (10) | |
C14 | 0.3448 (2) | 0.2169 (5) | 0.43938 (15) | 0.0571 (8) | |
H3 | 0.40560 | −0.04430 | 0.75210 | 0.0820* | |
H5 | 0.08110 | 0.23410 | 0.59160 | 0.0660* | |
H10 | 0.03990 | 0.26210 | 0.40140 | 0.0610* | |
H11 | 0.01950 | −0.03420 | 0.29690 | 0.0760* | |
H12 | 0.20060 | −0.17080 | 0.28150 | 0.0840* | |
H13 | 0.40250 | −0.01570 | 0.36930 | 0.0830* | |
H14 | 0.42670 | 0.27940 | 0.47540 | 0.0690* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S6 | 0.0495 (4) | 0.0456 (4) | 0.0578 (4) | −0.0051 (2) | 0.0233 (3) | −0.0002 (2) |
O7 | 0.0685 (12) | 0.0672 (12) | 0.0856 (13) | −0.0307 (9) | 0.0359 (10) | −0.0152 (9) |
O8 | 0.0649 (11) | 0.0535 (10) | 0.0728 (11) | 0.0154 (8) | 0.0294 (9) | 0.0070 (8) |
N1 | 0.0362 (10) | 0.0554 (11) | 0.0475 (10) | −0.0012 (8) | 0.0157 (8) | −0.0023 (8) |
N2 | 0.0364 (11) | 0.0825 (14) | 0.0552 (12) | 0.0041 (9) | 0.0119 (9) | 0.0021 (10) |
N4 | 0.0524 (13) | 0.0882 (16) | 0.0579 (13) | 0.0060 (11) | 0.0233 (10) | 0.0176 (11) |
C3 | 0.0553 (16) | 0.091 (2) | 0.0520 (14) | 0.0121 (14) | 0.0168 (12) | 0.0151 (14) |
C5 | 0.0398 (12) | 0.0713 (16) | 0.0545 (14) | 0.0006 (10) | 0.0203 (10) | 0.0069 (11) |
C9 | 0.0439 (12) | 0.0458 (12) | 0.0485 (11) | −0.0017 (9) | 0.0213 (9) | 0.0063 (9) |
C10 | 0.0410 (12) | 0.0577 (13) | 0.0547 (13) | −0.0007 (10) | 0.0205 (10) | 0.0034 (10) |
C11 | 0.0563 (15) | 0.0729 (17) | 0.0544 (14) | −0.0085 (12) | 0.0187 (12) | −0.0053 (12) |
C12 | 0.077 (2) | 0.0792 (18) | 0.0587 (16) | −0.0029 (15) | 0.0344 (14) | −0.0077 (13) |
C13 | 0.0652 (17) | 0.0837 (19) | 0.0727 (18) | 0.0071 (14) | 0.0431 (15) | −0.0014 (14) |
C14 | 0.0460 (13) | 0.0666 (15) | 0.0604 (14) | −0.0029 (11) | 0.0245 (11) | 0.0055 (11) |
Geometric parameters (Å, º) top
S6—O7 | 1.413 (3) | C10—C11 | 1.374 (4) |
S6—O8 | 1.422 (3) | C11—C12 | 1.376 (5) |
S6—N1 | 1.699 (3) | C12—C13 | 1.368 (5) |
S6—C9 | 1.741 (3) | C13—C14 | 1.381 (4) |
N1—N2 | 1.361 (3) | C3—H3 | 0.9293 |
N1—C5 | 1.346 (4) | C5—H5 | 0.9293 |
N2—C3 | 1.307 (4) | C10—H10 | 0.9307 |
N4—C3 | 1.347 (5) | C11—H11 | 0.9296 |
N4—C5 | 1.299 (4) | C12—H12 | 0.9297 |
C9—C10 | 1.383 (4) | C13—H13 | 0.9300 |
C9—C14 | 1.383 (4) | C14—H14 | 0.9303 |
| | | |
O7···N2 | 2.883 (5) | N4···H12vii | 2.5722 |
O7···C14i | 3.284 (5) | C3···N2viii | 3.425 (6) |
O8···C5ii | 3.296 (5) | C5···O8ix | 3.355 (5) |
O8···C5iii | 3.355 (5) | C5···O8ii | 3.296 (5) |
O8···C10iii | 3.406 (5) | C10···O8ix | 3.406 (5) |
O7···H14i | 2.6325 | C14···O7i | 3.284 (5) |
O7···H14 | 2.6202 | C11···H11x | 3.0472 |
O8···H5 | 2.7594 | H3···N2viii | 2.5529 |
O8···H10 | 2.5987 | H5···O8 | 2.7594 |
O8···H5ii | 2.3800 | H5···O8ii | 2.3800 |
N1···N4 | 2.172 (4) | H10···O8 | 2.5987 |
N2···O7 | 2.883 (5) | H11···C11xi | 3.0472 |
N2···N4 | 2.254 (4) | H11···N4vi | 2.8475 |
N2···C3iv | 3.425 (6) | H12···N4xii | 2.5722 |
N4···N1 | 2.172 (4) | H13···N2v | 2.9280 |
N2···H3iv | 2.5529 | H14···O7 | 2.6202 |
N2···H13v | 2.9280 | H14···O7i | 2.6325 |
N4···H11vi | 2.8475 | | |
| | | |
O7—S6—O8 | 121.63 (11) | C11—C12—C13 | 120.6 (3) |
O7—S6—N1 | 105.74 (11) | C12—C13—C14 | 120.4 (3) |
O7—S6—C9 | 110.69 (12) | C9—C14—C13 | 118.5 (2) |
O8—S6—N1 | 103.42 (11) | N2—C3—H3 | 121.87 |
O8—S6—C9 | 109.69 (11) | N4—C3—H3 | 121.84 |
N1—S6—C9 | 103.85 (10) | N1—C5—H5 | 124.76 |
S6—N1—N2 | 122.01 (17) | N4—C5—H5 | 124.87 |
S6—N1—C5 | 128.08 (17) | C9—C10—H10 | 120.56 |
N2—N1—C5 | 109.50 (19) | C11—C10—H10 | 120.54 |
N1—N2—C3 | 101.2 (2) | C10—C11—H11 | 119.91 |
C3—N4—C5 | 102.6 (2) | C12—C11—H11 | 119.91 |
N2—C3—N4 | 116.3 (3) | C11—C12—H12 | 119.70 |
N1—C5—N4 | 110.4 (2) | C13—C12—H12 | 119.72 |
S6—C9—C10 | 119.12 (19) | C12—C13—H13 | 119.77 |
S6—C9—C14 | 119.47 (18) | C14—C13—H13 | 119.78 |
C10—C9—C14 | 121.4 (2) | C9—C14—H14 | 120.79 |
C9—C10—C11 | 118.9 (3) | C13—C14—H14 | 120.70 |
C10—C11—C12 | 120.2 (3) | | |
| | | |
O7—S6—N1—N2 | −29.7 (2) | C5—N1—N2—C3 | −1.5 (3) |
O8—S6—N1—N2 | −158.55 (18) | N2—N1—C5—N4 | 1.3 (3) |
C9—S6—N1—N2 | 86.9 (2) | N1—N2—C3—N4 | 1.4 (3) |
O7—S6—N1—C5 | 158.5 (2) | C3—N4—C5—N1 | −0.4 (3) |
O8—S6—N1—C5 | 29.6 (2) | C5—N4—C3—N2 | −0.6 (3) |
C9—S6—N1—C5 | −85.0 (2) | S6—C9—C10—C11 | −178.39 (19) |
O7—S6—C9—C10 | −160.43 (18) | S6—C9—C14—C13 | 178.6 (2) |
O8—S6—C9—C10 | −23.5 (2) | C10—C9—C14—C13 | 0.2 (4) |
N1—S6—C9—C10 | 86.51 (19) | C14—C9—C10—C11 | 0.0 (4) |
O7—S6—C9—C14 | 21.1 (2) | C9—C10—C11—C12 | −0.2 (4) |
O8—S6—C9—C14 | 158.06 (18) | C10—C11—C12—C13 | 0.1 (4) |
N1—S6—C9—C14 | −91.9 (2) | C11—C12—C13—C14 | 0.2 (5) |
S6—N1—C5—N4 | 173.99 (18) | C12—C13—C14—C9 | −0.3 (4) |
S6—N1—N2—C3 | −174.74 (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, −y−1/2, z+1/2; (viii) −x+1, y−1/2, −z+3/2; (ix) x, y−1, z; (x) −x, y+1/2, −z+1/2; (xi) −x, y−1/2, −z+1/2; (xii) x, −y−1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N2viii | 0.93 | 2.55 | 3.425 (6) | 157 |
C5—H5···O8ii | 0.93 | 2.38 | 3.296 (5) | 169 |
C12—H12···N4xii | 0.93 | 2.57 | 3.490 (6) | 169 |
Symmetry codes: (ii) −x, −y+1, −z+1; (viii) −x+1, y−1/2, −z+3/2; (xii) x, −y−1/2, z−1/2. |