The title compound, C
15H
13N
3S, was prepared by the reaction of 1-(2-chloroethyl)benzene with hydrazine and phenyl isothiocyanate. Packing is stabilized by N—H
S intermolecular hydrogen bonds and C—H
π interactions.
Supporting information
CCDC reference: 269856
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.109
- Data-to-parameter ratio = 9.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT320_ALERT_2_C Check Hybridisation of C7 in Main Residue . ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT362_ALERT_2_C Short C(sp3)-C(sp2) Bond C7 - C8 ... 1.36 Ang.
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 26.95
From the CIF: _reflns_number_total 1605
Count of symmetry unique reflns 1450
Completeness (_total/calc) 110.69%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 155
Fraction of Friedel pairs measured 0.107
Are heavy atom types Z>Si present yes
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).
3-Benzyl-4-phenyl-1
H-1,2,4-triazole-5(4
H)-thione
top
Crystal data top
C15H13N3S | F(000) = 560 |
Mr = 267.34 | Dx = 1.341 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: c -2yc | Cell parameters from 25 reflections |
a = 15.277 (3) Å | θ = 4–14° |
b = 11.810 (2) Å | µ = 0.23 mm−1 |
c = 8.6360 (17) Å | T = 295 K |
β = 121.79 (3)° | Block, yellow |
V = 1324.4 (6) Å3 | 0.35 × 0.20 × 0.18 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.033 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.3° |
Graphite monochromator | h = −1→18 |
ω scans | k = −1→14 |
1763 measured reflections | l = −10→9 |
1605 independent reflections | 3 standard reflections every 100 reflections |
1506 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0827P)2 + 0.2246P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.35 e Å−3 |
1605 reflections | Δρmin = −0.35 e Å−3 |
173 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.073 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1450 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (2) |
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 | |
S1 | 0.15790 (5) | 0.11135 (7) | 0.02623 (7) | 0.0435 (2) | |
N1 | 0.34962 (19) | 0.1689 (2) | 0.3175 (3) | 0.0344 (5) | |
N2 | 0.3711 (2) | 0.0504 (2) | 0.5346 (3) | 0.0395 (5) | |
N3 | 0.28032 (19) | 0.0306 (2) | 0.3708 (3) | 0.0387 (5) | |
H3A | 0.2385 | −0.0229 | 0.3563 | 0.046* | |
C1 | 0.5520 (3) | 0.0898 (3) | 0.8992 (4) | 0.0449 (7) | |
H1A | 0.5045 | 0.0322 | 0.8373 | 0.054* | |
C2 | 0.6153 (3) | 0.0867 (3) | 1.0881 (5) | 0.0495 (7) | |
H2B | 0.6096 | 0.0268 | 1.1522 | 0.059* | |
C3 | 0.6866 (3) | 0.1715 (3) | 1.1819 (4) | 0.0518 (9) | |
H3B | 0.7287 | 0.1688 | 1.3082 | 0.062* | |
C4 | 0.6945 (3) | 0.2594 (3) | 1.0867 (5) | 0.0526 (8) | |
H4A | 0.7429 | 0.3161 | 1.1489 | 0.063* | |
C5 | 0.6315 (3) | 0.2650 (3) | 0.8993 (4) | 0.0454 (7) | |
H5A | 0.6366 | 0.3261 | 0.8365 | 0.055* | |
C6 | 0.5602 (2) | 0.1793 (2) | 0.8044 (4) | 0.0363 (6) | |
C7 | 0.5006 (2) | 0.1908 (2) | 0.6124 (3) | 0.0343 (6) | |
H7A | 0.4847 | 0.2708 | 0.5889 | 0.041* | |
H7B | 0.5467 | 0.1734 | 0.5701 | 0.041* | |
C8 | 0.4110 (2) | 0.1350 (2) | 0.4976 (4) | 0.0343 (6) | |
C9 | 0.2630 (2) | 0.1011 (2) | 0.2382 (4) | 0.0340 (6) | |
C10 | 0.3709 (2) | 0.2607 (2) | 0.2331 (3) | 0.0335 (5) | |
C11 | 0.3327 (3) | 0.3669 (3) | 0.2290 (5) | 0.0482 (7) | |
H11A | 0.2886 | 0.3784 | 0.2711 | 0.058* | |
C12 | 0.3613 (4) | 0.4567 (3) | 0.1608 (6) | 0.0587 (9) | |
H12A | 0.3366 | 0.5291 | 0.1578 | 0.070* | |
C13 | 0.4258 (3) | 0.4385 (3) | 0.0980 (5) | 0.0537 (9) | |
H13A | 0.4460 | 0.4993 | 0.0555 | 0.064* | |
C14 | 0.4610 (3) | 0.3319 (3) | 0.0969 (5) | 0.0528 (8) | |
H14A | 0.5036 | 0.3202 | 0.0515 | 0.063* | |
C15 | 0.4326 (3) | 0.2416 (3) | 0.1637 (5) | 0.0445 (7) | |
H15A | 0.4550 | 0.1687 | 0.1616 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0314 (4) | 0.0638 (5) | 0.0284 (3) | 0.0050 (3) | 0.0111 (3) | −0.0042 (3) |
N1 | 0.0332 (12) | 0.0424 (12) | 0.0234 (10) | −0.0009 (9) | 0.0119 (9) | 0.0004 (8) |
N2 | 0.0360 (13) | 0.0456 (12) | 0.0299 (11) | −0.0041 (10) | 0.0126 (10) | 0.0030 (9) |
N3 | 0.0321 (12) | 0.0461 (12) | 0.0339 (12) | −0.0028 (10) | 0.0146 (11) | 0.0015 (9) |
C1 | 0.0463 (17) | 0.0469 (15) | 0.0330 (15) | −0.0060 (13) | 0.0151 (14) | 0.0045 (11) |
C2 | 0.0519 (19) | 0.0558 (16) | 0.0367 (16) | 0.0047 (16) | 0.0205 (15) | 0.0100 (13) |
C3 | 0.0405 (18) | 0.078 (2) | 0.0259 (14) | 0.0031 (16) | 0.0101 (13) | −0.0019 (13) |
C4 | 0.0408 (16) | 0.073 (2) | 0.0394 (17) | −0.0170 (16) | 0.0178 (14) | −0.0129 (15) |
C5 | 0.0430 (17) | 0.0577 (17) | 0.0370 (15) | −0.0142 (14) | 0.0220 (14) | −0.0038 (12) |
C6 | 0.0327 (13) | 0.0479 (16) | 0.0266 (13) | −0.0007 (11) | 0.0144 (11) | 0.0015 (10) |
C7 | 0.0350 (13) | 0.0425 (13) | 0.0202 (11) | −0.0123 (11) | 0.0111 (10) | 0.0020 (9) |
C8 | 0.0335 (14) | 0.0431 (13) | 0.0242 (12) | −0.0009 (11) | 0.0138 (11) | 0.0011 (10) |
C9 | 0.0284 (13) | 0.0426 (13) | 0.0291 (13) | 0.0016 (10) | 0.0139 (11) | −0.0024 (10) |
C10 | 0.0339 (12) | 0.0409 (13) | 0.0213 (11) | −0.0023 (10) | 0.0115 (10) | 0.0009 (9) |
C11 | 0.062 (2) | 0.0476 (16) | 0.0430 (16) | 0.0091 (15) | 0.0332 (16) | −0.0006 (13) |
C12 | 0.082 (3) | 0.0398 (15) | 0.0536 (19) | 0.0059 (17) | 0.0349 (19) | 0.0026 (14) |
C13 | 0.058 (2) | 0.0557 (18) | 0.0359 (16) | −0.0108 (16) | 0.0168 (15) | 0.0095 (13) |
C14 | 0.0479 (18) | 0.071 (2) | 0.0468 (19) | 0.0056 (16) | 0.0297 (16) | 0.0143 (16) |
C15 | 0.0454 (17) | 0.0489 (16) | 0.0447 (16) | 0.0107 (13) | 0.0274 (15) | 0.0086 (13) |
Geometric parameters (Å, º) top
S1—C9 | 1.687 (3) | C5—C6 | 1.393 (4) |
N1—C9 | 1.380 (4) | C5—H5A | 0.9300 |
N1—C8 | 1.386 (3) | C6—C7 | 1.417 (3) |
N1—C10 | 1.436 (4) | C7—C8 | 1.363 (4) |
N2—C8 | 1.295 (4) | C7—H7A | 0.9700 |
N2—N3 | 1.383 (4) | C7—H7B | 0.9700 |
N3—C9 | 1.325 (4) | C10—C11 | 1.376 (4) |
N3—H3A | 0.8600 | C10—C15 | 1.376 (4) |
C1—C6 | 1.383 (4) | C11—C12 | 1.391 (5) |
C1—C2 | 1.391 (5) | C11—H11A | 0.9300 |
C1—H1A | 0.9300 | C12—C13 | 1.368 (7) |
C2—C3 | 1.384 (5) | C12—H12A | 0.9300 |
C2—H2B | 0.9300 | C13—C14 | 1.372 (6) |
C3—C4 | 1.369 (6) | C13—H13A | 0.9300 |
C3—H3B | 0.9300 | C14—C15 | 1.386 (5) |
C4—C5 | 1.381 (5) | C14—H14A | 0.9300 |
C4—H4A | 0.9300 | C15—H15A | 0.9300 |
| | | |
C9—N1—C8 | 107.2 (2) | C8—C7—H7B | 105.9 |
C9—N1—C10 | 126.9 (2) | C6—C7—H7B | 105.9 |
C8—N1—C10 | 125.9 (2) | H7A—C7—H7B | 106.2 |
C8—N2—N3 | 103.1 (2) | N2—C8—C7 | 128.0 (3) |
C9—N3—N2 | 114.5 (2) | N2—C8—N1 | 111.8 (2) |
C9—N3—H3A | 122.8 | C7—C8—N1 | 120.2 (3) |
N2—N3—H3A | 122.8 | N3—C9—N1 | 103.4 (2) |
C6—C1—C2 | 119.3 (3) | N3—C9—S1 | 128.7 (2) |
C6—C1—H1A | 120.3 | N1—C9—S1 | 127.8 (2) |
C2—C1—H1A | 120.3 | C11—C10—C15 | 121.1 (3) |
C3—C2—C1 | 121.0 (3) | C11—C10—N1 | 119.7 (3) |
C3—C2—H2B | 119.5 | C15—C10—N1 | 119.2 (3) |
C1—C2—H2B | 119.5 | C10—C11—C12 | 118.9 (3) |
C4—C3—C2 | 119.2 (3) | C10—C11—H11A | 120.6 |
C4—C3—H3B | 120.4 | C12—C11—H11A | 120.6 |
C2—C3—H3B | 120.4 | C13—C12—C11 | 120.0 (3) |
C3—C4—C5 | 120.8 (3) | C13—C12—H12A | 120.0 |
C3—C4—H4A | 119.6 | C11—C12—H12A | 120.0 |
C5—C4—H4A | 119.6 | C12—C13—C14 | 120.9 (3) |
C4—C5—C6 | 120.1 (3) | C12—C13—H13A | 119.6 |
C4—C5—H5A | 120.0 | C14—C13—H13A | 119.6 |
C6—C5—H5A | 120.0 | C13—C14—C15 | 119.6 (3) |
C1—C6—C5 | 119.6 (3) | C13—C14—H14A | 120.2 |
C1—C6—C7 | 124.3 (3) | C15—C14—H14A | 120.2 |
C5—C6—C7 | 116.1 (2) | C10—C15—C14 | 119.4 (3) |
C8—C7—C6 | 125.8 (2) | C10—C15—H15A | 120.3 |
C8—C7—H7A | 105.9 | C14—C15—H15A | 120.3 |
C6—C7—H7A | 105.9 | | |
| | | |
C8—N2—N3—C9 | −1.2 (3) | N2—N3—C9—N1 | 2.3 (3) |
C6—C1—C2—C3 | −0.4 (6) | N2—N3—C9—S1 | −174.6 (2) |
C1—C2—C3—C4 | 0.1 (6) | C8—N1—C9—N3 | −2.3 (3) |
C2—C3—C4—C5 | 0.8 (6) | C10—N1—C9—N3 | −179.8 (3) |
C3—C4—C5—C6 | −1.4 (6) | C8—N1—C9—S1 | 174.6 (2) |
C2—C1—C6—C5 | −0.2 (5) | C10—N1—C9—S1 | −2.9 (4) |
C2—C1—C6—C7 | 179.4 (3) | C9—N1—C10—C11 | 84.7 (4) |
C4—C5—C6—C1 | 1.0 (5) | C8—N1—C10—C11 | −92.3 (4) |
C4—C5—C6—C7 | −178.6 (3) | C9—N1—C10—C15 | −97.7 (4) |
C1—C6—C7—C8 | 17.9 (5) | C8—N1—C10—C15 | 85.3 (3) |
C5—C6—C7—C8 | −162.5 (3) | C15—C10—C11—C12 | −3.0 (5) |
N3—N2—C8—C7 | 178.5 (3) | N1—C10—C11—C12 | 174.6 (3) |
N3—N2—C8—N1 | −0.4 (3) | C10—C11—C12—C13 | 0.5 (6) |
C6—C7—C8—N2 | −11.2 (5) | C11—C12—C13—C14 | 1.7 (6) |
C6—C7—C8—N1 | 167.6 (3) | C12—C13—C14—C15 | −1.3 (6) |
C9—N1—C8—N2 | 1.7 (3) | C11—C10—C15—C14 | 3.3 (5) |
C10—N1—C8—N2 | 179.3 (3) | N1—C10—C15—C14 | −174.2 (3) |
C9—N1—C8—C7 | −177.2 (3) | C13—C14—C15—C10 | −1.1 (5) |
C10—N1—C8—C7 | 0.3 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···S1i | 0.86 | 2.58 | 3.279 (3) | 139 |
C14—H14A···Cg1ii | 0.93 | 2.74 | 3.565 (2) | 149 |
C3—H3B···Cg2iii | 0.93 | 2.79 | 3.690 (2) | 164 |
Symmetry codes: (i) x, −y, z+1/2; (ii) x, y, z−1; (iii) x+1/2, −y+1/2, z+3/2. |