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The title compound, C
12H
13ClN
4OS, was prepared by the reaction of 4-amino-3-(3-hydroxypropyl)-1,2,4-triazole-5-thione and 4-chlorobenzaldehyde. The configuration at the azomethine C=N bond is
E and the compound can be assigned as the thione tautomeric form. The crystal packing is stabilized by O—H
N and O—H
S intermolecular hydrogen-bonding interactions.
Supporting information
CCDC reference: 629668
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.004 Å
- R factor = 0.047
- wR factor = 0.113
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.
4-[(4-Chlorobenzylidene)amino]-3-(3-hydroxypropyl)-1,2,4-triazole-5-thione
top
Crystal data top
C12H13ClN4OS | Z = 2 |
Mr = 296.77 | F(000) = 308 |
Triclinic, P1 | Dx = 1.464 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1880 (6) Å | Cell parameters from 1694 reflections |
b = 7.5476 (7) Å | θ = 2.7–24.9° |
c = 14.6378 (14) Å | µ = 0.44 mm−1 |
α = 91.610 (2)° | T = 298 K |
β = 97.999 (2)° | Block, colourless |
γ = 95.695 (2)° | 0.27 × 0.20 × 0.17 mm |
V = 673.05 (11) Å3 | |
Data collection top
Bruker APEX area-detector diffractometer | 2342 independent reflections |
Radiation source: fine-focus sealed tube | 2117 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −7→7 |
Tmin = 0.891, Tmax = 0.930 | k = −8→8 |
3560 measured reflections | l = −17→8 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.3229P] where P = (Fo2 + 2Fc2)/3 |
2342 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
Experimental. Spectroscopic analysis: IR (KBr): 3418, 3329, 2940, 1586, 1275 cm-1. |
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 | |
Cl1 | 1.35634 (14) | 0.19177 (12) | 0.51723 (6) | 0.0727 (3) | |
S1 | 0.51393 (11) | 0.92889 (8) | 0.73662 (5) | 0.0479 (2) | |
O1 | −0.0045 (3) | 0.0319 (2) | 0.86319 (14) | 0.0490 (5) | |
H1 | −0.1233 | 0.0110 | 0.8302 | 0.073* | |
N1 | 0.6302 (3) | 0.4951 (3) | 0.76705 (14) | 0.0387 (5) | |
N2 | 0.4879 (3) | 0.5903 (2) | 0.80949 (13) | 0.0325 (4) | |
N3 | 0.2706 (3) | 0.7641 (3) | 0.85390 (14) | 0.0402 (5) | |
H3 | 0.2035 | 0.8567 | 0.8618 | 0.048* | |
N4 | 0.2248 (3) | 0.6064 (3) | 0.89565 (14) | 0.0395 (5) | |
C1 | 1.1893 (4) | 0.3036 (4) | 0.58016 (18) | 0.0458 (6) | |
C2 | 1.0308 (5) | 0.2069 (4) | 0.6205 (2) | 0.0549 (7) | |
H2 | 1.0171 | 0.0830 | 0.6165 | 0.066* | |
C3 | 0.8929 (4) | 0.2953 (3) | 0.66695 (19) | 0.0477 (7) | |
H3A | 0.7843 | 0.2303 | 0.6938 | 0.057* | |
C4 | 0.9129 (4) | 0.4801 (3) | 0.67451 (16) | 0.0361 (5) | |
C5 | 1.0753 (4) | 0.5738 (3) | 0.63276 (17) | 0.0401 (6) | |
H5 | 1.0900 | 0.6977 | 0.6364 | 0.048* | |
C6 | 1.2141 (4) | 0.4863 (4) | 0.58631 (18) | 0.0446 (6) | |
H6 | 1.3234 | 0.5501 | 0.5594 | 0.053* | |
C7 | 0.7669 (4) | 0.5773 (3) | 0.72240 (17) | 0.0399 (6) | |
H7 | 0.7743 | 0.7008 | 0.7201 | 0.048* | |
C8 | 0.4281 (4) | 0.7615 (3) | 0.80015 (16) | 0.0356 (5) | |
C9 | 0.3582 (4) | 0.5026 (3) | 0.86723 (16) | 0.0335 (5) | |
C10 | 0.3824 (4) | 0.3163 (3) | 0.89429 (18) | 0.0395 (6) | |
H10A | 0.5326 | 0.3089 | 0.9223 | 0.047* | |
H10B | 0.3541 | 0.2383 | 0.8392 | 0.047* | |
C11 | 0.2277 (4) | 0.2507 (3) | 0.96198 (17) | 0.0425 (6) | |
H11A | 0.2869 | 0.1518 | 0.9943 | 0.051* | |
H11B | 0.2239 | 0.3458 | 1.0075 | 0.051* | |
C12 | −0.0036 (4) | 0.1913 (3) | 0.91758 (18) | 0.0419 (6) | |
H12A | −0.0975 | 0.1702 | 0.9648 | 0.050* | |
H12B | −0.0595 | 0.2836 | 0.8789 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0715 (5) | 0.0793 (6) | 0.0791 (6) | 0.0277 (4) | 0.0381 (5) | 0.0000 (4) |
S1 | 0.0490 (4) | 0.0342 (4) | 0.0620 (5) | 0.0022 (3) | 0.0127 (3) | 0.0110 (3) |
O1 | 0.0423 (10) | 0.0390 (10) | 0.0649 (13) | 0.0086 (8) | 0.0040 (9) | −0.0061 (9) |
N1 | 0.0380 (11) | 0.0390 (11) | 0.0421 (11) | 0.0082 (9) | 0.0135 (9) | 0.0029 (9) |
N2 | 0.0325 (10) | 0.0303 (10) | 0.0357 (11) | 0.0042 (8) | 0.0074 (8) | 0.0008 (8) |
N3 | 0.0445 (12) | 0.0293 (10) | 0.0489 (12) | 0.0085 (8) | 0.0113 (10) | −0.0017 (9) |
N4 | 0.0435 (12) | 0.0352 (11) | 0.0422 (12) | 0.0068 (9) | 0.0128 (10) | 0.0017 (9) |
C1 | 0.0422 (14) | 0.0575 (17) | 0.0404 (14) | 0.0142 (12) | 0.0097 (12) | 0.0012 (12) |
C2 | 0.0657 (18) | 0.0391 (15) | 0.0659 (19) | 0.0122 (13) | 0.0257 (15) | 0.0055 (13) |
C3 | 0.0515 (15) | 0.0409 (14) | 0.0563 (17) | 0.0043 (11) | 0.0252 (13) | 0.0117 (12) |
C4 | 0.0353 (12) | 0.0402 (13) | 0.0327 (12) | 0.0028 (10) | 0.0046 (10) | 0.0025 (10) |
C5 | 0.0401 (13) | 0.0381 (13) | 0.0412 (14) | −0.0020 (10) | 0.0069 (11) | 0.0025 (11) |
C6 | 0.0361 (13) | 0.0570 (16) | 0.0414 (14) | −0.0014 (11) | 0.0122 (11) | 0.0039 (12) |
C7 | 0.0406 (13) | 0.0351 (13) | 0.0445 (14) | 0.0022 (10) | 0.0096 (11) | 0.0006 (11) |
C8 | 0.0339 (12) | 0.0317 (12) | 0.0396 (13) | 0.0016 (9) | 0.0019 (10) | −0.0035 (10) |
C9 | 0.0331 (12) | 0.0344 (12) | 0.0323 (12) | 0.0007 (9) | 0.0049 (10) | −0.0007 (10) |
C10 | 0.0379 (13) | 0.0347 (13) | 0.0476 (15) | 0.0058 (10) | 0.0100 (11) | 0.0038 (11) |
C11 | 0.0467 (14) | 0.0403 (14) | 0.0405 (14) | 0.0036 (11) | 0.0066 (12) | 0.0058 (11) |
C12 | 0.0428 (14) | 0.0374 (13) | 0.0492 (15) | 0.0096 (10) | 0.0155 (12) | 0.0047 (11) |
Geometric parameters (Å, º) top
Cl1—C1 | 1.739 (3) | C3—H3A | 0.9300 |
S1—C8 | 1.677 (2) | C4—C5 | 1.392 (3) |
O1—C12 | 1.423 (3) | C4—C7 | 1.458 (3) |
O1—H1 | 0.8200 | C5—C6 | 1.373 (3) |
N1—C7 | 1.265 (3) | C5—H5 | 0.9300 |
N1—N2 | 1.389 (3) | C6—H6 | 0.9300 |
N2—C9 | 1.383 (3) | C7—H7 | 0.9300 |
N2—C8 | 1.385 (3) | C9—C10 | 1.487 (3) |
N3—C8 | 1.336 (3) | C10—C11 | 1.530 (3) |
N3—N4 | 1.376 (3) | C10—H10A | 0.9700 |
N3—H3 | 0.8600 | C10—H10B | 0.9700 |
N4—C9 | 1.294 (3) | C11—C12 | 1.506 (3) |
C1—C6 | 1.371 (4) | C11—H11A | 0.9700 |
C1—C2 | 1.374 (4) | C11—H11B | 0.9700 |
C2—C3 | 1.373 (4) | C12—H12A | 0.9700 |
C2—H2 | 0.9300 | C12—H12B | 0.9700 |
C3—C4 | 1.388 (3) | | |
| | | |
C12—O1—H1 | 109.5 | N1—C7—C4 | 120.5 (2) |
C7—N1—N2 | 119.4 (2) | N1—C7—H7 | 119.7 |
C9—N2—C8 | 108.29 (18) | C4—C7—H7 | 119.7 |
C9—N2—N1 | 118.71 (18) | N3—C8—N2 | 102.42 (19) |
C8—N2—N1 | 132.70 (19) | N3—C8—S1 | 125.93 (18) |
C8—N3—N4 | 114.36 (19) | N2—C8—S1 | 131.62 (18) |
C8—N3—H3 | 122.8 | N4—C9—N2 | 110.8 (2) |
N4—N3—H3 | 122.8 | N4—C9—C10 | 126.4 (2) |
C9—N4—N3 | 104.09 (18) | N2—C9—C10 | 122.7 (2) |
C6—C1—C2 | 121.3 (2) | C9—C10—C11 | 113.2 (2) |
C6—C1—Cl1 | 119.5 (2) | C9—C10—H10A | 108.9 |
C2—C1—Cl1 | 119.2 (2) | C11—C10—H10A | 108.9 |
C3—C2—C1 | 119.2 (2) | C9—C10—H10B | 108.9 |
C3—C2—H2 | 120.4 | C11—C10—H10B | 108.9 |
C1—C2—H2 | 120.4 | H10A—C10—H10B | 107.8 |
C2—C3—C4 | 121.1 (2) | C12—C11—C10 | 114.3 (2) |
C2—C3—H3A | 119.5 | C12—C11—H11A | 108.7 |
C4—C3—H3A | 119.5 | C10—C11—H11A | 108.7 |
C3—C4—C5 | 118.2 (2) | C12—C11—H11B | 108.7 |
C3—C4—C7 | 122.2 (2) | C10—C11—H11B | 108.7 |
C5—C4—C7 | 119.6 (2) | H11A—C11—H11B | 107.6 |
C6—C5—C4 | 121.1 (2) | O1—C12—C11 | 109.1 (2) |
C6—C5—H5 | 119.5 | O1—C12—H12A | 109.9 |
C4—C5—H5 | 119.5 | C11—C12—H12A | 109.9 |
C1—C6—C5 | 119.1 (2) | O1—C12—H12B | 109.9 |
C1—C6—H6 | 120.4 | C11—C12—H12B | 109.9 |
C5—C6—H6 | 120.4 | H12A—C12—H12B | 108.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.86 | 1.94 | 2.780 (3) | 167 |
O1—H1···S1ii | 0.82 | 2.47 | 3.2922 (19) | 176 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z. |
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