


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681004571X/jh2226sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053681004571X/jh2226Isup2.hkl |
CCDC reference: 803157
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.137
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5875 PLAT023_ALERT_3_C Resolution (too) Low [sin(theta)/Lambda < 0.6].. 64.93 Deg. PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given ..... ? PLAT731_ALERT_1_C Bond Calc 0.93(3), Rep 0.931(10) ...... 3.00 su-Ra O1W -H2W 1.555 1.555 # 41 PLAT735_ALERT_1_C D-H Calc 0.93(3), Rep 0.931(10) ...... 3.00 su-Ra O1W -H2W 1.555 1.555 # 41
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Water H atoms were located in a difference Fourier map and isotropically refined with O—H distance restraints of 0.90 (1) Å. All the other H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.93(aromatic),0.96(methyl) and 0.97Å (methylene),N—H = 0.86Å and refined using a riding model with Uiso(H) = 1.2Ueq or 1.5Ueq (parent atom).In the absence of significant anomalous scattering effects,Friedel pairs were merged.
Triazole compounds and their derivatives have many applications in industry and medicine. Ionic liquids consisting of imidazolium and triazolium salts have attracted increasing interest as an alternative to classical organic solvents for a wide range of chemical syntheses, biocatalysis, electrochemical applications, energetic materials, nano-rods, liquid-liquid separation and polymerization. These interesting liquids containing imidazole and triazole ring systems have unique physical and chemical properties: low melting point, very low vapour pressure, a large liquid phase range, tunable miscibility, and good hydrolytic and thermal stability (Ustabaş et al., 2006). In the field of medicine triazole derivatives were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti- inflammatory, anticancer and antioxidant properties. A few derivatives of triazoles have exhibited antimicrobial activity. Some of the drugs such as ribavirin (antiviral agent), rizatriptan (anti migraine agent), alprazolam (anxiolytic agent), fluconazole and itraconazole (antifungal agents) are the best examples for potent molecules possessing the triazole nucleus (Fun et al., 2010). Furthermore, in many compounds, the thiophene unit is associated with high anticancer and antifungal activity (Kalkan et al., 2007). In a previous paper, we reported the 1,2,4 triazole derivative with different substituents. We report here the crystal structure of the title compound (I) (Fig.1) in order to examine the structure activity of 1,2,4 triazole with a thiophene substituent.
Compound (I) contains three planar rings (Fig.1), namely a triazole ring N1/N2/C7/N3/C6 (A), an imidazole ring N4/C12/C13/N5/C14 (B) and a thiophene ring C1/C2/C3/C4/S1 (C). The dihedral angle between rings A/B, A/C and B/C are 48.15 (8)°, 84.92 (8)° and 74.73 (9)°, respectively. In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The C—N bond lengths in the triazole ring of all molecules lie in the range of 1.260 (3)–1.349 (4) Å. These are longer than a typical double C═N bond [1.269 (2) Å], but shorter than a C—N single bond [1.443 (4) Å]. The bond length N2—C7 [1.306 (3) Å] and N3—C7 [1.365 (3) Å] are in agreement with the corresponding values in similar structures containing triazole ring such as [1.290 (3)Å and 1.384 (3) Å; Yılmaz et al., 2006], [1.287 (4)Å and 1.374 (4) Å; Ustabaş et al., 2007] and [1.292 (3)Å and 1.373 (3) Å; Ustabaş et al., 2009]. The N1—N2 [1.389 (3) Å] bond length is close to that reported for similar compounds [1.388 (2)Å Ünver et al., 2006] and [1.398 (4)Å Ustabaş, Çoruh, Sancak, Ünver & Vázquez-López (2006)]. Atom N3 has a trigonal configuration, the sum of three bond angles around them being 360° (Kalkan et al., 2007). The bond lengths and angles in the imidazole and thiophenyl rings are normal. In the thiophenyl ring S1—C4 [1.711 (2) Å] bond is longer than S1—C1 [1.699 (3) Å] bond. These S—C distances are in agreement with the corresponding values of those found in other structures containing thiophene, [1.706 (2)Å and 1.723 (2) Å; Ünver et al., 2006], [1.710 (5)Å and 1.724 (4) Å; Ustabaş,Çoruh, Sancak, Ünver & Vázquez-López (2006)],[1.701 (3)Å and 1.712 (2) Å; Yılmaz et al., 2006], [1.685 (5)Å and 1.692 (6) Å; Ustabaş et al., 2007] and [1.698 (3)Å and 1.735 (6) Å; Ustabaş et al., 2009]. The exocyclic bond angles N1—C6—C5 and N2—C7—C8 are 125.08 (18)° and 125.73 (19)°, respectively. These increase from the normal value of 120° might be the consequence of repulsion between the lone pair of electrons on atom N1 and H5B attached to C5(N1···H5B = 2.563 Å) and on atom N2 and H8A attached to C8(N2···H8B = 2.566 Å), respectively. The widening of the excocyclic angles N3—C9—C10 [112.3 (16)°]and C9—C10—C11 [112.5 (19)°] from the normal 109° may be due to the steric repulsion between H8B and H10A (H8B ··· H10A = 2.547 Å) and H9A and H10B (H9A··· H10B = 2.357 Å), respectively. The C10—C11—N4 exocyclic angle [112.13 (18)°] deviate from the normal value of 109° may be due to the consequence of repulsion between the lone pair of electrons on atom N4 and H11A and H11B attached to C11 (N4···H11A = 1.998Å and N4···H11B = 1.998 Å). The C11—N4—C14 exocyclic angle [127.4 (2)°] significantly deviate from the normal value of 120° may be due to the consequence of repulsion between the lone pair of electrons on atom N4 and H14 at C14 (N4···H14 = 2.019 Å). The N3—C9—C10—C11 torsion angle of 178.95 (18)° indicates that the triazole ring and the immidazole moiety has an E-Configuration across the C9—C10 bond. The C9—N3—C6—C5 torsion angle of 4.3 (3)° indicates that the imidazole moiety and the thiophenyl moiety are in Z-Configuration across the N3—N6 bond. The water molecule is involved in the intermolecular O–H···N hydrogen bonding (Table 2), which is effective in stabilizing the crystal structure.
For details of the synthesis, see: Ünver et al. (2009). For related structures, see: Fun et al. (2010); Kalkan et al. (2007); Ustabaş et al. (2007, 2009); Ünver et al. (2006). For the biological activity of triazoles, see: Ustabaş, et al. (2006a,b); Yılmaz et al. (2006). For bond-length data, see: Allen et al. (1987).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
C14H17N5S·H2O | F(000) = 648 |
Mr = 305.40 | Dx = 1.285 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
a = 9.5584 (12) Å | Cell parameters from 25 reflections |
b = 9.4873 (10) Å | θ = 20–30° |
c = 17.644 (3) Å | µ = 1.88 mm−1 |
β = 99.360 (12)° | T = 293 K |
V = 1578.7 (4) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 2679 independent reflections |
Radiation source: fine-focus sealed tube | 2336 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 2 pixels mm-1 | θmax = 64.9°, θmin = 4.7° |
ω–2θ scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.603, Tmax = 0.705 | l = −20→20 |
2855 measured reflections |
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)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0774P)2 + 0.5509P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max = 0.001 |
2679 reflections | Δρmax = 0.31 e Å−3 |
200 parameters | Δρmin = −0.34 e Å−3 |
3 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.042 (2) |
C14H17N5S·H2O | V = 1578.7 (4) Å3 |
Mr = 305.40 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.5584 (12) Å | µ = 1.88 mm−1 |
b = 9.4873 (10) Å | T = 293 K |
c = 17.644 (3) Å | 0.30 × 0.25 × 0.20 mm |
β = 99.360 (12)° |
Enraf–Nonius CAD-4 diffractometer | 2679 independent reflections |
Absorption correction: ψ scan (North et al., 1968) | 2336 reflections with I > 2σ(I) |
Tmin = 0.603, Tmax = 0.705 | Rint = 0.016 |
2855 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 3 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.31 e Å−3 |
2679 reflections | Δρmin = −0.34 e Å−3 |
200 parameters |
Experimental. North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.37723 (6) | 0.43126 (6) | 0.61955 (4) | 0.0582 (3) | |
N3 | 0.39660 (16) | 0.21826 (17) | 0.81129 (9) | 0.0356 (4) | |
N1 | 0.61089 (18) | 0.2561 (2) | 0.78623 (10) | 0.0442 (5) | |
N4 | 0.01247 (18) | −0.0268 (2) | 0.74184 (11) | 0.0456 (5) | |
N2 | 0.60666 (18) | 0.29618 (19) | 0.86153 (10) | 0.0437 (5) | |
C4 | 0.3386 (2) | 0.2567 (2) | 0.62899 (11) | 0.0410 (5) | |
C7 | 0.4785 (2) | 0.2729 (2) | 0.87518 (11) | 0.0393 (5) | |
N5 | −0.1397 (2) | 0.0259 (3) | 0.63795 (14) | 0.0662 (6) | |
C9 | 0.2487 (2) | 0.1719 (2) | 0.80399 (12) | 0.0410 (5) | |
H9A | 0.2041 | 0.1797 | 0.7507 | 0.049* | |
H9B | 0.1983 | 0.2336 | 0.8342 | 0.049* | |
C5 | 0.4407 (2) | 0.1592 (2) | 0.67757 (12) | 0.0465 (5) | |
H5A | 0.3968 | 0.0672 | 0.6789 | 0.056* | |
H5B | 0.5246 | 0.1482 | 0.6537 | 0.056* | |
C3 | 0.2087 (2) | 0.2246 (3) | 0.58660 (12) | 0.0494 (6) | |
H3 | 0.1678 | 0.1355 | 0.5844 | 0.059* | |
C12 | 0.0596 (2) | −0.0922 (3) | 0.68159 (14) | 0.0501 (6) | |
H12 | 0.1401 | −0.1480 | 0.6836 | 0.060* | |
C8 | 0.4268 (3) | 0.3028 (3) | 0.94823 (13) | 0.0592 (7) | |
H8A | 0.5039 | 0.3365 | 0.9855 | 0.089* | |
H8B | 0.3892 | 0.2180 | 0.9668 | 0.089* | |
H8C | 0.3538 | 0.3731 | 0.9397 | 0.089* | |
C10 | 0.2361 (2) | 0.0211 (2) | 0.83060 (12) | 0.0446 (5) | |
H10A | 0.2792 | 0.0138 | 0.8842 | 0.053* | |
H10B | 0.2880 | −0.0403 | 0.8011 | 0.053* | |
C6 | 0.4841 (2) | 0.2100 (2) | 0.75747 (11) | 0.0372 (5) | |
C2 | 0.1441 (2) | 0.3447 (3) | 0.54633 (14) | 0.0570 (6) | |
H2 | 0.0564 | 0.3420 | 0.5145 | 0.068* | |
C1 | 0.2227 (3) | 0.4610 (3) | 0.55909 (15) | 0.0586 (6) | |
H1 | 0.1960 | 0.5483 | 0.5374 | 0.070* | |
C13 | −0.0351 (3) | −0.0591 (3) | 0.61877 (15) | 0.0588 (7) | |
H13 | −0.0299 | −0.0897 | 0.5692 | 0.071* | |
C11 | 0.0822 (2) | −0.0285 (3) | 0.82172 (13) | 0.0548 (6) | |
H11A | 0.0798 | −0.1236 | 0.8417 | 0.066* | |
H11B | 0.0305 | 0.0320 | 0.8518 | 0.066* | |
C14 | −0.1074 (2) | 0.0419 (3) | 0.71219 (17) | 0.0590 (7) | |
H14 | −0.1611 | 0.0948 | 0.7413 | 0.071* | |
O1W | 0.8146 (3) | 0.2886 (3) | 1.00449 (18) | 0.1142 (11) | |
H1W | 0.758 (3) | 0.312 (4) | 0.9581 (11) | 0.111 (13)* | |
H2W | 0.801 (5) | 0.341 (5) | 1.0473 (14) | 0.16 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0574 (4) | 0.0422 (4) | 0.0688 (5) | −0.0088 (2) | −0.0084 (3) | −0.0012 (3) |
N3 | 0.0323 (8) | 0.0379 (9) | 0.0360 (8) | 0.0000 (7) | 0.0033 (6) | 0.0008 (7) |
N1 | 0.0393 (9) | 0.0478 (11) | 0.0460 (10) | −0.0052 (8) | 0.0085 (7) | 0.0062 (8) |
N4 | 0.0333 (9) | 0.0503 (11) | 0.0529 (11) | −0.0075 (8) | 0.0058 (7) | 0.0015 (8) |
N2 | 0.0399 (9) | 0.0454 (10) | 0.0439 (9) | −0.0064 (8) | 0.0011 (7) | 0.0028 (8) |
C4 | 0.0495 (11) | 0.0409 (11) | 0.0327 (10) | −0.0069 (9) | 0.0067 (8) | −0.0032 (8) |
C7 | 0.0404 (10) | 0.0398 (11) | 0.0361 (10) | −0.0002 (8) | 0.0017 (8) | 0.0022 (8) |
N5 | 0.0560 (13) | 0.0636 (14) | 0.0717 (14) | −0.0045 (11) | −0.0115 (11) | 0.0065 (11) |
C9 | 0.0293 (10) | 0.0478 (12) | 0.0450 (11) | 0.0017 (8) | 0.0031 (8) | 0.0009 (9) |
C5 | 0.0562 (13) | 0.0422 (12) | 0.0415 (11) | 0.0023 (10) | 0.0093 (10) | −0.0024 (9) |
C3 | 0.0529 (13) | 0.0553 (14) | 0.0406 (11) | −0.0170 (10) | 0.0090 (9) | −0.0014 (10) |
C12 | 0.0404 (11) | 0.0507 (13) | 0.0604 (14) | −0.0112 (10) | 0.0117 (10) | −0.0003 (11) |
C8 | 0.0567 (14) | 0.0789 (18) | 0.0412 (12) | −0.0017 (13) | 0.0053 (10) | −0.0093 (11) |
C10 | 0.0368 (11) | 0.0516 (13) | 0.0440 (11) | −0.0037 (9) | 0.0025 (8) | 0.0046 (9) |
C6 | 0.0394 (10) | 0.0334 (10) | 0.0393 (10) | 0.0016 (8) | 0.0081 (8) | 0.0050 (8) |
C2 | 0.0408 (12) | 0.0800 (18) | 0.0484 (13) | −0.0049 (11) | 0.0021 (10) | −0.0044 (12) |
C1 | 0.0578 (14) | 0.0577 (15) | 0.0579 (14) | 0.0098 (12) | 0.0017 (11) | 0.0059 (11) |
C13 | 0.0603 (15) | 0.0606 (15) | 0.0547 (14) | −0.0212 (12) | 0.0066 (11) | −0.0003 (11) |
C11 | 0.0428 (12) | 0.0710 (16) | 0.0514 (13) | −0.0128 (11) | 0.0103 (10) | 0.0055 (11) |
C14 | 0.0404 (12) | 0.0542 (15) | 0.0798 (18) | −0.0017 (10) | 0.0017 (11) | −0.0041 (12) |
O1W | 0.1007 (18) | 0.106 (2) | 0.113 (2) | 0.0367 (15) | −0.0494 (16) | −0.0440 (17) |
S1—C1 | 1.699 (3) | C5—H5B | 0.9700 |
S1—C4 | 1.711 (2) | C3—C2 | 1.429 (4) |
N3—C7 | 1.365 (3) | C3—H3 | 0.9300 |
N3—C6 | 1.366 (3) | C12—C13 | 1.349 (4) |
N3—C9 | 1.466 (2) | C12—H12 | 0.9300 |
N1—C6 | 1.311 (3) | C8—H8A | 0.9600 |
N1—N2 | 1.389 (3) | C8—H8B | 0.9600 |
N4—C14 | 1.348 (3) | C8—H8C | 0.9600 |
N4—C12 | 1.369 (3) | C10—C11 | 1.528 (3) |
N4—C11 | 1.458 (3) | C10—H10A | 0.9700 |
N2—C7 | 1.306 (3) | C10—H10B | 0.9700 |
C4—C3 | 1.376 (3) | C2—C1 | 1.333 (4) |
C4—C5 | 1.507 (3) | C2—H2 | 0.9300 |
C7—C8 | 1.481 (3) | C1—H1 | 0.9300 |
N5—C14 | 1.305 (4) | C13—H13 | 0.9300 |
N5—C13 | 1.369 (4) | C11—H11A | 0.9700 |
C9—C10 | 1.516 (3) | C11—H11B | 0.9700 |
C9—H9A | 0.9700 | C14—H14 | 0.9300 |
C9—H9B | 0.9700 | O1W—H1W | 0.933 (10) |
C5—C6 | 1.484 (3) | O1W—H2W | 0.931 (10) |
C5—H5A | 0.9700 | ||
C1—S1—C4 | 92.43 (12) | C7—C8—H8A | 109.5 |
C7—N3—C6 | 105.21 (16) | C7—C8—H8B | 109.5 |
C7—N3—C9 | 126.96 (17) | H8A—C8—H8B | 109.5 |
C6—N3—C9 | 127.76 (17) | C7—C8—H8C | 109.5 |
C6—N1—N2 | 107.03 (16) | H8A—C8—H8C | 109.5 |
C14—N4—C12 | 106.5 (2) | H8B—C8—H8C | 109.5 |
C14—N4—C11 | 127.4 (2) | C9—C10—C11 | 112.50 (19) |
C12—N4—C11 | 126.1 (2) | C9—C10—H10A | 109.1 |
C7—N2—N1 | 107.71 (16) | C11—C10—H10A | 109.1 |
C3—C4—C5 | 128.1 (2) | C9—C10—H10B | 109.1 |
C3—C4—S1 | 110.58 (17) | C11—C10—H10B | 109.1 |
C5—C4—S1 | 121.31 (16) | H10A—C10—H10B | 107.8 |
N2—C7—N3 | 109.94 (18) | N1—C6—N3 | 110.11 (17) |
N2—C7—C8 | 125.73 (19) | N1—C6—C5 | 125.08 (18) |
N3—C7—C8 | 124.32 (19) | N3—C6—C5 | 124.80 (18) |
C14—N5—C13 | 104.7 (2) | C1—C2—C3 | 112.9 (2) |
N3—C9—C10 | 112.32 (16) | C1—C2—H2 | 123.5 |
N3—C9—H9A | 109.1 | C3—C2—H2 | 123.5 |
C10—C9—H9A | 109.1 | C2—C1—S1 | 112.2 (2) |
N3—C9—H9B | 109.1 | C2—C1—H1 | 123.9 |
C10—C9—H9B | 109.1 | S1—C1—H1 | 123.9 |
H9A—C9—H9B | 107.9 | C12—C13—N5 | 110.7 (2) |
C6—C5—C4 | 113.35 (18) | C12—C13—H13 | 124.7 |
C6—C5—H5A | 108.9 | N5—C13—H13 | 124.7 |
C4—C5—H5A | 108.9 | N4—C11—C10 | 112.13 (18) |
C6—C5—H5B | 108.9 | N4—C11—H11A | 109.2 |
C4—C5—H5B | 108.9 | C10—C11—H11A | 109.2 |
H5A—C5—H5B | 107.7 | N4—C11—H11B | 109.2 |
C4—C3—C2 | 111.9 (2) | C10—C11—H11B | 109.2 |
C4—C3—H3 | 124.1 | H11A—C11—H11B | 107.9 |
C2—C3—H3 | 124.1 | N5—C14—N4 | 112.3 (2) |
C13—C12—N4 | 105.7 (2) | N5—C14—H14 | 123.8 |
C13—C12—H12 | 127.1 | N4—C14—H14 | 123.8 |
N4—C12—H12 | 127.1 | H1W—O1W—H2W | 116.6 (17) |
C6—N1—N2—C7 | 0.0 (2) | C4—C5—C6—N3 | 68.3 (3) |
C1—S1—C4—C3 | −0.50 (17) | C4—C3—C2—C1 | −0.6 (3) |
C1—S1—C4—C5 | 178.72 (18) | C3—C2—C1—S1 | 0.2 (3) |
N1—N2—C7—N3 | 0.0 (2) | C4—S1—C1—C2 | 0.2 (2) |
N1—N2—C7—C8 | −179.0 (2) | N4—C12—C13—N5 | 0.3 (3) |
C6—N3—C7—N2 | −0.1 (2) | C14—N5—C13—C12 | −0.5 (3) |
C9—N3—C7—N2 | 177.05 (18) | C14—N4—C11—C10 | −123.4 (3) |
C6—N3—C7—C8 | 179.0 (2) | C12—N4—C11—C10 | 54.5 (3) |
C9—N3—C7—C8 | −3.9 (3) | C9—C10—C11—N4 | 61.6 (3) |
C7—N3—C9—C10 | −85.2 (2) | C13—N5—C14—N4 | 0.5 (3) |
C6—N3—C9—C10 | 91.3 (2) | C12—N4—C14—N5 | −0.3 (3) |
C3—C4—C5—C6 | −126.8 (2) | C11—N4—C14—N5 | 177.9 (2) |
S1—C4—C5—C6 | 54.2 (2) | C3—C4—C5—C6 | −126.8 (2) |
C5—C4—C3—C2 | −178.5 (2) | S1—C4—C5—C6 | 54.2 (2) |
S1—C4—C3—C2 | 0.7 (2) | C4—C5—C6—N3 | 68.3 (3) |
C14—N4—C12—C13 | 0.0 (2) | C4—C5—C6—N1 | −110.2 (2) |
C11—N4—C12—C13 | −178.3 (2) | C5—C6—N3—C9 | 4.3 (3) |
N3—C9—C10—C11 | −178.95 (18) | C6—N3—C9—C10 | 91.3 (2) |
N2—N1—C6—N3 | 0.0 (2) | N3—C9—C10—C11 | −178.95 (18) |
N2—N1—C6—C5 | 178.65 (19) | C9—C10—C11—N4 | 61.6 (3) |
C7—N3—C6—N1 | 0.0 (2) | C10—C11—N4—C12 | 54.5 (3) |
C9—N3—C6—N1 | −177.03 (18) | C10—C11—N4—C14 | −123.4 (3) |
C7—N3—C6—C5 | −178.63 (19) | C8—C7—N3—C9 | −3.9 (3) |
C9—N3—C6—C5 | 4.3 (3) | C7—N3—C9—C10 | −85.2 (2) |
C4—C5—C6—N1 | −110.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···N5i | 0.93 (1) | 2.04 (2) | 2.915 (4) | 155 (4) |
O1W—H1W···N2 | 0.93 (1) | 2.05 (2) | 2.948 (3) | 161 (4) |
Symmetry code: (i) x+1, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H17N5S·H2O |
Mr | 305.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 9.5584 (12), 9.4873 (10), 17.644 (3) |
β (°) | 99.360 (12) |
V (Å3) | 1578.7 (4) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.88 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.603, 0.705 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2855, 2679, 2336 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.587 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.137, 1.12 |
No. of reflections | 2679 |
No. of parameters | 200 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.34 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), MolEN (Fair, 1990), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and ZORTEP (Zsolnai, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2W···N5i | 0.931 (10) | 2.04 (2) | 2.915 (4) | 155 (4) |
O1W—H1W···N2 | 0.933 (10) | 2.051 (17) | 2.948 (3) | 161 (4) |
Symmetry code: (i) x+1, −y+1/2, z+1/2. |
Triazole compounds and their derivatives have many applications in industry and medicine. Ionic liquids consisting of imidazolium and triazolium salts have attracted increasing interest as an alternative to classical organic solvents for a wide range of chemical syntheses, biocatalysis, electrochemical applications, energetic materials, nano-rods, liquid-liquid separation and polymerization. These interesting liquids containing imidazole and triazole ring systems have unique physical and chemical properties: low melting point, very low vapour pressure, a large liquid phase range, tunable miscibility, and good hydrolytic and thermal stability (Ustabaş et al., 2006). In the field of medicine triazole derivatives were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti- inflammatory, anticancer and antioxidant properties. A few derivatives of triazoles have exhibited antimicrobial activity. Some of the drugs such as ribavirin (antiviral agent), rizatriptan (anti migraine agent), alprazolam (anxiolytic agent), fluconazole and itraconazole (antifungal agents) are the best examples for potent molecules possessing the triazole nucleus (Fun et al., 2010). Furthermore, in many compounds, the thiophene unit is associated with high anticancer and antifungal activity (Kalkan et al., 2007). In a previous paper, we reported the 1,2,4 triazole derivative with different substituents. We report here the crystal structure of the title compound (I) (Fig.1) in order to examine the structure activity of 1,2,4 triazole with a thiophene substituent.
Compound (I) contains three planar rings (Fig.1), namely a triazole ring N1/N2/C7/N3/C6 (A), an imidazole ring N4/C12/C13/N5/C14 (B) and a thiophene ring C1/C2/C3/C4/S1 (C). The dihedral angle between rings A/B, A/C and B/C are 48.15 (8)°, 84.92 (8)° and 74.73 (9)°, respectively. In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The C—N bond lengths in the triazole ring of all molecules lie in the range of 1.260 (3)–1.349 (4) Å. These are longer than a typical double C═N bond [1.269 (2) Å], but shorter than a C—N single bond [1.443 (4) Å]. The bond length N2—C7 [1.306 (3) Å] and N3—C7 [1.365 (3) Å] are in agreement with the corresponding values in similar structures containing triazole ring such as [1.290 (3)Å and 1.384 (3) Å; Yılmaz et al., 2006], [1.287 (4)Å and 1.374 (4) Å; Ustabaş et al., 2007] and [1.292 (3)Å and 1.373 (3) Å; Ustabaş et al., 2009]. The N1—N2 [1.389 (3) Å] bond length is close to that reported for similar compounds [1.388 (2)Å Ünver et al., 2006] and [1.398 (4)Å Ustabaş, Çoruh, Sancak, Ünver & Vázquez-López (2006)]. Atom N3 has a trigonal configuration, the sum of three bond angles around them being 360° (Kalkan et al., 2007). The bond lengths and angles in the imidazole and thiophenyl rings are normal. In the thiophenyl ring S1—C4 [1.711 (2) Å] bond is longer than S1—C1 [1.699 (3) Å] bond. These S—C distances are in agreement with the corresponding values of those found in other structures containing thiophene, [1.706 (2)Å and 1.723 (2) Å; Ünver et al., 2006], [1.710 (5)Å and 1.724 (4) Å; Ustabaş,Çoruh, Sancak, Ünver & Vázquez-López (2006)],[1.701 (3)Å and 1.712 (2) Å; Yılmaz et al., 2006], [1.685 (5)Å and 1.692 (6) Å; Ustabaş et al., 2007] and [1.698 (3)Å and 1.735 (6) Å; Ustabaş et al., 2009]. The exocyclic bond angles N1—C6—C5 and N2—C7—C8 are 125.08 (18)° and 125.73 (19)°, respectively. These increase from the normal value of 120° might be the consequence of repulsion between the lone pair of electrons on atom N1 and H5B attached to C5(N1···H5B = 2.563 Å) and on atom N2 and H8A attached to C8(N2···H8B = 2.566 Å), respectively. The widening of the excocyclic angles N3—C9—C10 [112.3 (16)°]and C9—C10—C11 [112.5 (19)°] from the normal 109° may be due to the steric repulsion between H8B and H10A (H8B ··· H10A = 2.547 Å) and H9A and H10B (H9A··· H10B = 2.357 Å), respectively. The C10—C11—N4 exocyclic angle [112.13 (18)°] deviate from the normal value of 109° may be due to the consequence of repulsion between the lone pair of electrons on atom N4 and H11A and H11B attached to C11 (N4···H11A = 1.998Å and N4···H11B = 1.998 Å). The C11—N4—C14 exocyclic angle [127.4 (2)°] significantly deviate from the normal value of 120° may be due to the consequence of repulsion between the lone pair of electrons on atom N4 and H14 at C14 (N4···H14 = 2.019 Å). The N3—C9—C10—C11 torsion angle of 178.95 (18)° indicates that the triazole ring and the immidazole moiety has an E-Configuration across the C9—C10 bond. The C9—N3—C6—C5 torsion angle of 4.3 (3)° indicates that the imidazole moiety and the thiophenyl moiety are in Z-Configuration across the N3—N6 bond. The water molecule is involved in the intermolecular O–H···N hydrogen bonding (Table 2), which is effective in stabilizing the crystal structure.