In the title compound, C
16H
15N
3S, the phenyl rings make dihedral angles of 73.0 (1) and 87.9 (1)° with the triazole ring. The molecular and crystal structures are stabilized by two intramolecular hydrogen bonds (C—H
S and C—H
N) and one intermolecular C—H
N hydrogen bond. The latter links molecules into infinite chains.
Supporting information
CCDC reference: 625015
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.125
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.879
Tmax scaled 0.872 Tmin scaled 0.686
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
1-benzyl-3-(benzylsulfanyl)-1
H-1,2,4-triazole
top
Crystal data top
C16H15N3S | F(000) = 592 |
Mr = 281.37 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 5.9390 (8) Å | θ = 19.3–23.6° |
b = 25.276 (5) Å | µ = 1.96 mm−1 |
c = 9.567 (2) Å | T = 293 K |
β = 99.12 (1)° | Prism, colourless |
V = 1418.0 (5) Å3 | 0.20 × 0.10 × 0.07 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2232 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 74.2°, θmin = 3.5° |
profile data from ω/2θ scans | h = 0→7 |
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989) | k = 0→31 |
Tmin = 0.780, Tmax = 0.992 | l = −11→11 |
3166 measured reflections | 3 standard reflections every 200 reflections |
2890 independent reflections | intensity decay: none |
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)] = 0.043 | All H-atom parameters refined |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0712P)2 + 0.3185P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
2890 reflections | Δρmax = 0.27 e Å−3 |
242 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0046 (6) |
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 | x | y | z | Uiso*/Ueq | |
S3 | 0.19203 (10) | 0.13906 (2) | 0.46808 (5) | 0.0559 (2) | |
N1 | 0.5290 (3) | 0.23268 (6) | 0.72858 (15) | 0.0416 (5) | |
N2 | 0.4976 (3) | 0.20580 (7) | 0.60302 (16) | 0.0464 (5) | |
N4 | 0.2147 (3) | 0.18813 (7) | 0.72853 (18) | 0.0495 (6) | |
C3 | 0.3061 (3) | 0.17980 (7) | 0.60977 (18) | 0.0404 (5) | |
C5 | 0.3618 (4) | 0.22139 (8) | 0.7995 (2) | 0.0472 (6) | |
C6 | −0.0676 (4) | 0.11566 (9) | 0.5238 (3) | 0.0528 (7) | |
C7 | −0.0506 (3) | 0.06674 (7) | 0.6147 (2) | 0.0424 (5) | |
C8 | 0.1445 (4) | 0.05228 (9) | 0.7052 (3) | 0.0577 (7) | |
C9 | 0.1474 (5) | 0.00793 (10) | 0.7894 (3) | 0.0679 (9) | |
C10 | −0.0431 (5) | −0.02321 (10) | 0.7834 (3) | 0.0651 (8) | |
C11 | −0.2389 (5) | −0.00935 (10) | 0.6945 (3) | 0.0645 (8) | |
C12 | −0.2434 (4) | 0.03517 (9) | 0.6110 (2) | 0.0532 (7) | |
C13 | 0.7222 (4) | 0.26911 (9) | 0.7645 (2) | 0.0486 (6) | |
C14 | 0.7120 (3) | 0.31311 (7) | 0.65751 (19) | 0.0420 (5) | |
C15 | 0.8754 (4) | 0.31663 (9) | 0.5690 (2) | 0.0506 (7) | |
C16 | 0.8626 (4) | 0.35618 (9) | 0.4677 (2) | 0.0588 (8) | |
C17 | 0.6874 (4) | 0.39188 (9) | 0.4534 (2) | 0.0596 (8) | |
C18 | 0.5233 (4) | 0.38892 (9) | 0.5411 (3) | 0.0591 (8) | |
C19 | 0.5365 (4) | 0.34981 (8) | 0.6425 (2) | 0.0513 (7) | |
H5 | 0.354 (4) | 0.2367 (9) | 0.885 (3) | 0.061 (7)* | |
H8 | 0.282 (5) | 0.0745 (11) | 0.712 (3) | 0.076 (8)* | |
H9 | 0.283 (5) | −0.0030 (11) | 0.852 (3) | 0.081 (8)* | |
H10 | −0.038 (5) | −0.0526 (11) | 0.838 (3) | 0.078 (8)* | |
H11 | −0.369 (5) | −0.0309 (12) | 0.688 (3) | 0.089 (9)* | |
H12 | −0.378 (4) | 0.0460 (9) | 0.547 (3) | 0.067 (7)* | |
H15 | 1.004 (4) | 0.2896 (10) | 0.580 (3) | 0.067 (7)* | |
H16 | 0.980 (5) | 0.3562 (11) | 0.412 (3) | 0.087 (9)* | |
H17 | 0.671 (5) | 0.4194 (11) | 0.387 (3) | 0.075 (8)* | |
H18 | 0.397 (4) | 0.4157 (10) | 0.529 (3) | 0.070 (7)* | |
H19 | 0.428 (4) | 0.3469 (10) | 0.705 (3) | 0.066 (7)* | |
H61 | −0.164 (4) | 0.1076 (10) | 0.435 (3) | 0.063 (7)* | |
H62 | −0.126 (4) | 0.1451 (9) | 0.574 (3) | 0.058 (7)* | |
H131 | 0.713 (4) | 0.2830 (10) | 0.859 (3) | 0.066 (7)* | |
H132 | 0.861 (4) | 0.2482 (9) | 0.771 (2) | 0.059 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S3 | 0.0736 (4) | 0.0539 (3) | 0.0419 (3) | −0.0158 (3) | 0.0146 (2) | −0.0066 (2) |
N1 | 0.0473 (9) | 0.0427 (8) | 0.0354 (8) | −0.0030 (7) | 0.0084 (6) | 0.0017 (6) |
N2 | 0.0551 (9) | 0.0483 (9) | 0.0380 (8) | −0.0064 (7) | 0.0137 (7) | −0.0025 (7) |
N4 | 0.0545 (10) | 0.0533 (10) | 0.0445 (9) | −0.0060 (8) | 0.0197 (7) | −0.0038 (7) |
C3 | 0.0490 (10) | 0.0374 (9) | 0.0364 (9) | 0.0008 (8) | 0.0113 (7) | 0.0053 (7) |
C5 | 0.0558 (11) | 0.0517 (11) | 0.0366 (9) | −0.0021 (9) | 0.0151 (8) | −0.0027 (8) |
C6 | 0.0515 (11) | 0.0483 (11) | 0.0560 (12) | −0.0028 (9) | 0.0002 (10) | 0.0030 (10) |
C7 | 0.0439 (10) | 0.0401 (9) | 0.0433 (9) | −0.0009 (8) | 0.0074 (8) | −0.0052 (7) |
C8 | 0.0478 (11) | 0.0523 (12) | 0.0704 (14) | −0.0037 (10) | 0.0013 (10) | 0.0102 (10) |
C9 | 0.0654 (15) | 0.0593 (14) | 0.0741 (16) | 0.0038 (12) | −0.0043 (12) | 0.0172 (12) |
C10 | 0.0846 (17) | 0.0472 (12) | 0.0646 (14) | −0.0043 (12) | 0.0152 (13) | 0.0102 (11) |
C11 | 0.0696 (15) | 0.0541 (13) | 0.0702 (15) | −0.0182 (11) | 0.0120 (12) | −0.0016 (11) |
C12 | 0.0510 (11) | 0.0529 (12) | 0.0539 (12) | −0.0070 (9) | 0.0028 (10) | −0.0049 (9) |
C13 | 0.0488 (11) | 0.0522 (11) | 0.0436 (11) | −0.0069 (9) | 0.0033 (8) | 0.0026 (9) |
C14 | 0.0436 (9) | 0.0444 (10) | 0.0385 (9) | −0.0091 (8) | 0.0081 (7) | −0.0048 (7) |
C15 | 0.0485 (11) | 0.0544 (12) | 0.0522 (11) | −0.0047 (9) | 0.0178 (9) | −0.0064 (9) |
C16 | 0.0654 (14) | 0.0641 (14) | 0.0525 (12) | −0.0163 (11) | 0.0262 (11) | −0.0047 (10) |
C17 | 0.0775 (15) | 0.0512 (12) | 0.0504 (12) | −0.0129 (11) | 0.0111 (11) | 0.0064 (10) |
C18 | 0.0650 (14) | 0.0495 (12) | 0.0635 (14) | 0.0036 (10) | 0.0127 (11) | 0.0035 (10) |
C19 | 0.0514 (11) | 0.0545 (12) | 0.0510 (11) | −0.0008 (9) | 0.0171 (9) | −0.0021 (9) |
Geometric parameters (Å, º) top
S3—C3 | 1.7509 (18) | C16—C17 | 1.368 (3) |
S3—C6 | 1.809 (3) | C17—C18 | 1.385 (3) |
N1—N2 | 1.367 (2) | C18—C19 | 1.379 (3) |
N1—C5 | 1.320 (3) | C5—H5 | 0.91 (3) |
N1—C13 | 1.469 (3) | C6—H61 | 0.97 (3) |
N2—C3 | 1.324 (3) | C6—H62 | 0.98 (2) |
N4—C3 | 1.351 (2) | C8—H8 | 0.98 (3) |
N4—C5 | 1.320 (3) | C9—H9 | 0.96 (3) |
C6—C7 | 1.506 (3) | C10—H10 | 0.91 (3) |
C7—C8 | 1.381 (3) | C11—H11 | 0.94 (3) |
C7—C12 | 1.391 (3) | C12—H12 | 0.97 (3) |
C8—C9 | 1.379 (4) | C13—H131 | 0.98 (3) |
C9—C10 | 1.372 (4) | C13—H132 | 0.97 (2) |
C10—C11 | 1.373 (4) | C15—H15 | 1.02 (2) |
C11—C12 | 1.378 (3) | C16—H16 | 0.94 (3) |
C13—C14 | 1.506 (3) | C17—H17 | 0.94 (3) |
C14—C15 | 1.388 (3) | C18—H18 | 1.00 (2) |
C14—C19 | 1.386 (3) | C19—H19 | 0.95 (3) |
C15—C16 | 1.386 (3) | | |
| | | |
C3—S3—C6 | 102.0 (1) | S3—C6—H61 | 102.9 (15) |
N2—N1—C5 | 109.6 (2) | S3—C6—H62 | 106.3 (14) |
N2—N1—C13 | 120.7 (2) | C7—C6—H61 | 108.1 (15) |
C5—N1—C13 | 129.7 (2) | C7—C6—H62 | 109.7 (16) |
N1—N2—C3 | 101.7 (2) | H61—C6—H62 | 113 (2) |
C3—N4—C5 | 102.2 (2) | C7—C8—H8 | 119.7 (17) |
S3—C3—N2 | 119.0 (1) | C9—C8—H8 | 119.4 (17) |
S3—C3—N4 | 125.8 (1) | C8—C9—H9 | 121.8 (17) |
N2—C3—N4 | 115.2 (2) | C10—C9—H9 | 117.6 (17) |
N1—C5—N4 | 111.3 (2) | C9—C10—H10 | 119.6 (19) |
S3—C6—C7 | 117.2 (2) | C11—C10—H10 | 120.9 (19) |
C6—C7—C8 | 123.5 (2) | C10—C11—H11 | 120.0 (18) |
C6—C7—C12 | 118.5 (2) | C12—C11—H11 | 119.7 (18) |
C8—C7—C12 | 117.99 (18) | C7—C12—H12 | 116.6 (14) |
C7—C8—C9 | 120.9 (2) | C11—C12—H12 | 122.5 (14) |
C8—C9—C10 | 120.5 (3) | N1—C13—H131 | 106.6 (14) |
C9—C10—C11 | 119.4 (2) | N1—C13—H132 | 107.3 (14) |
C10—C11—C12 | 120.3 (3) | C14—C13—H131 | 111.1 (15) |
C7—C12—C11 | 120.9 (2) | C14—C13—H132 | 112.8 (13) |
N1—C13—C14 | 111.0 (2) | H131—C13—H132 | 107.8 (19) |
C13—C14—C15 | 120.34 (18) | C14—C15—H15 | 118.7 (15) |
C13—C14—C19 | 120.88 (18) | C16—C15—H15 | 120.9 (15) |
C15—C14—C19 | 118.75 (18) | C15—C16—H16 | 115.6 (17) |
C14—C15—C16 | 120.4 (2) | C17—C16—H16 | 124.2 (17) |
C15—C16—C17 | 120.2 (2) | C16—C17—H17 | 123.6 (18) |
C16—C17—C18 | 120.1 (2) | C18—C17—H17 | 116.3 (18) |
C17—C18—C19 | 119.9 (2) | C17—C18—H18 | 118.6 (15) |
C14—C19—C18 | 120.7 (2) | C19—C18—H18 | 121.5 (15) |
N1—C5—H5 | 121.2 (15) | C14—C19—H19 | 117.2 (16) |
N4—C5—H5 | 127.4 (15) | C18—C19—H19 | 122.0 (16) |
| | | |
C6—S3—C3—N2 | −177.61 (16) | C6—C7—C8—C9 | 177.8 (2) |
C6—S3—C3—N4 | 1.66 (19) | C12—C7—C8—C9 | −0.1 (3) |
C3—S3—C6—C7 | −87.29 (19) | C8—C7—C12—C11 | −0.4 (3) |
N2—N1—C5—N4 | −0.4 (2) | C7—C8—C9—C10 | 0.9 (4) |
C13—N1—C5—N4 | 177.26 (19) | C8—C9—C10—C11 | −1.2 (4) |
N2—N1—C13—C14 | 60.3 (2) | C9—C10—C11—C12 | 0.6 (4) |
C5—N1—C13—C14 | −117.2 (2) | C10—C11—C12—C7 | 0.2 (4) |
C5—N1—N2—C3 | 0.2 (2) | N1—C13—C14—C15 | −112.8 (2) |
C13—N1—N2—C3 | −177.74 (17) | N1—C13—C14—C19 | 65.3 (2) |
N1—N2—C3—S3 | 179.45 (13) | C13—C14—C19—C18 | −177.7 (2) |
N1—N2—C3—N4 | 0.1 (2) | C15—C14—C19—C18 | 0.4 (3) |
C5—N4—C3—S3 | −179.62 (15) | C13—C14—C15—C16 | 178.12 (19) |
C3—N4—C5—N1 | 0.4 (2) | C19—C14—C15—C16 | 0.0 (3) |
C5—N4—C3—N2 | −0.3 (2) | C14—C15—C16—C17 | −0.5 (3) |
S3—C6—C7—C12 | −153.32 (17) | C15—C16—C17—C18 | 0.6 (3) |
S3—C6—C7—C8 | 28.8 (3) | C16—C17—C18—C19 | −0.2 (4) |
C6—C7—C12—C11 | −178.5 (2) | C17—C18—C19—C14 | −0.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N2i | 0.91 (3) | 2.57 (3) | 3.424 (3) | 155 (2) |
C8—H8···S3 | 0.98 (3) | 2.83 (3) | 3.200 (3) | 103 (2) |
C6—H62···N4 | 0.98 (2) | 2.55 (3) | 2.994 (3) | 107 (2) |
Symmetry code: (i) x, −y+1/2, z+1/2. |