organic compounds
4-(2-Methoxyphenyl)-3-(3,4,5-trimethoxyphenethyl)-2H-1,2,4-triazole-5(4H)-thione
aDepartment of Chemistry, Quaid-i-Azam Univeristy, Islamabad 45320, Pakistan, and bSchool of Chemistry and Materials Science Centre, University of Manchester, Oxford Road, Manchester M13 9PL, England
*Correspondence e-mail: nasimhrama@yahoo.com
The title compound, C20H23N3O4S, is an important biologically active heterocyclic compound. The five-membered ring is oriented with respect to the six-membered rings at dihedral angles of 78.60 (3) (trimethoxyphenyl ring) and 71.57 (3)° (methoxyphenyl ring). In the intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains along the c axis.
Related literature
For general background, see: Holla et al. (1998); Turan-Zitouni et al. (1999); Demirbas et al. (2002); Paulvannan et al. (2000); Kritsanida et al. (2002); Omar et al. (1986). For related structures, see: Öztürk et al. (2004a,b); Zhang et al. (2004). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536807066433/hk2411sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066433/hk2411Isup2.hkl
The synthesis of the title compound was carried out by refluxing a solution of 1-(3-(3,4,5-trimethoxyphenyl)propanoyl)-4-(2-methoxyphenyl)thiosemicarbazide (4.19 g, 10 mmol) in NaOH (2 M) for 5 h. Single crystals suitable for X-ray analysis were obtained by recrystallization from an aqeous ethanol solution at room temperature (yield: 82%; m.p. 491–492 K).
H2N (for NH) was located in difference syntheses and refined isotropically [N2—H2N = 0.878 (17) Å and Uiso(H) = 0.022 (4) Å2]. The remaining H atoms were positioned geometrically, with C—H = 0.95, 0.99 and 0.98 Å for aromatic, methylene and methyl H atoms, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.
Substituted triazole derivatives display significant biological activities including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). The biological activity is closely related to the structure, possibly being due to the presence of the —N—C ?S unit (Omar et al., 1986). We are interested in the synthesis and biological activities of aryloxyacetyl hydrazide derivatives and report herein the synthesis and
of the title compound, (I).In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987), and are comparable with those observed in related structures Öztürk et al., 2004a,b). The C2?S1 [1.6775 (14) Å] bond is in accordance with the corresponding values of 1.6773 (19) Å in 4-(4-chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione Öztürk et al., 2004a) and 1.668 (5) Å in 4-amino-3-(1,2,3,4,5-pentahydroxypentyl)-1H-1,2,4-triazole-5(4H)-thione (Zhang et al., 2004). In the triazole ring, the N2 ?C2 [1.3326 (19) Å] bond shows double-bond character.
The rings A (N1–N3/C1/C2), B (C5–C10) and C (C14–C19) are, of course, planar and dihedral angles between them are A/B = 78.60 (3)°, A/C = 71.57 (3)° and B/C = 74.12 (3)°.
In the
intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the c axis (Fig. 2), in which they may be effective in the stabilization of the structure.For general background, see: Holla et al. (1998); Turan-Zitouni et al. (1999); Demirbas et al. (2002); Paulvannan et al. (2000); Kritsanida et al. (2002); Omar et al. (1986). For related structures, see: Öztürk et al. (2004a,b); Zhang et al. (2004). For bond-length data, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).C20H23N3O4S | Z = 2 |
Mr = 401.47 | F(000) = 424 |
Triclinic, P1 | Dx = 1.294 Mg m−3 |
Hall symbol: -P 1 | Melting point: 491(1) K |
a = 8.6368 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5422 (7) Å | Cell parameters from 5348 reflections |
c = 11.6944 (8) Å | θ = 2.4–26.4° |
α = 91.733 (1)° | µ = 0.19 mm−1 |
β = 92.955 (1)° | T = 100 K |
γ = 104.075 (1)° | Rectangular, colourless |
V = 1030.44 (12) Å3 | 0.55 × 0.35 × 0.30 mm |
Bruker SMART CCD area-detector diffractometer | 4149 independent reflections |
Radiation source: fine-focus sealed tube | 3689 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ω and φ scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: integration (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.926, Tmax = 0.946 | k = −13→12 |
8266 measured reflections | l = −14→14 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0399P)2 + 0.3128P] where P = (Fo2 + 2Fc2)/3 |
4149 reflections | (Δ/σ)max = 0.001 |
261 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C20H23N3O4S | γ = 104.075 (1)° |
Mr = 401.47 | V = 1030.44 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6368 (6) Å | Mo Kα radiation |
b = 10.5422 (7) Å | µ = 0.19 mm−1 |
c = 11.6944 (8) Å | T = 100 K |
α = 91.733 (1)° | 0.55 × 0.35 × 0.30 mm |
β = 92.955 (1)° |
Bruker SMART CCD area-detector diffractometer | 4149 independent reflections |
Absorption correction: integration (SADABS; Sheldrick, 1996) | 3689 reflections with I > 2σ(I) |
Tmin = 0.926, Tmax = 0.946 | Rint = 0.061 |
8266 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.31 e Å−3 |
4149 reflections | Δρmin = −0.25 e Å−3 |
261 parameters |
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 | 1.22156 (4) | 0.29397 (4) | 1.24108 (3) | 0.02234 (11) | |
O1 | 0.73558 (18) | 0.35378 (12) | 0.44984 (10) | 0.0440 (3) | |
O2 | 0.73876 (11) | 0.15824 (11) | 0.30066 (8) | 0.0224 (2) | |
O3 | 0.76675 (13) | −0.07402 (10) | 0.37013 (8) | 0.0262 (2) | |
O4 | 1.16300 (12) | 0.44582 (10) | 0.89915 (9) | 0.0260 (2) | |
N1 | 0.87413 (14) | 0.11839 (12) | 1.02120 (9) | 0.0201 (3) | |
N2 | 0.94616 (14) | 0.15655 (12) | 1.12957 (10) | 0.0193 (2) | |
H2N | 0.8869 (19) | 0.1498 (17) | 1.1889 (15) | 0.022 (4)* | |
N3 | 1.12777 (13) | 0.22471 (11) | 1.01432 (9) | 0.0177 (2) | |
C1 | 0.98802 (16) | 0.16129 (14) | 0.95339 (11) | 0.0187 (3) | |
C2 | 1.09805 (17) | 0.22420 (14) | 1.12896 (11) | 0.0185 (3) | |
C3 | 0.97520 (16) | 0.15040 (14) | 0.82582 (11) | 0.0210 (3) | |
H3A | 1.0517 | 0.1012 | 0.7992 | 0.025* | |
H3B | 1.0058 | 0.2393 | 0.7958 | 0.025* | |
C4 | 0.80733 (17) | 0.08197 (15) | 0.77691 (11) | 0.0213 (3) | |
H4A | 0.7863 | −0.0128 | 0.7904 | 0.026* | |
H4B | 0.7277 | 0.1174 | 0.8169 | 0.026* | |
C5 | 0.78916 (16) | 0.10143 (14) | 0.64979 (11) | 0.0198 (3) | |
C6 | 0.77190 (19) | 0.22128 (15) | 0.61242 (12) | 0.0268 (3) | |
H6 | 0.7712 | 0.2900 | 0.6667 | 0.032* | |
C7 | 0.75566 (19) | 0.24094 (16) | 0.49577 (13) | 0.0267 (3) | |
C8 | 0.75539 (16) | 0.13938 (14) | 0.41670 (11) | 0.0201 (3) | |
C9 | 0.77218 (16) | 0.01948 (14) | 0.45455 (11) | 0.0193 (3) | |
C10 | 0.79036 (16) | 0.00040 (14) | 0.57146 (12) | 0.0199 (3) | |
H10 | 0.8035 | −0.0812 | 0.5972 | 0.024* | |
C11 | 0.7409 (4) | 0.4614 (2) | 0.52929 (18) | 0.0692 (8) | |
H11A | 0.6571 | 0.4357 | 0.5834 | 0.104* | |
H11B | 0.7236 | 0.5364 | 0.4873 | 0.104* | |
H11C | 0.8457 | 0.4857 | 0.5714 | 0.104* | |
C12 | 0.57722 (19) | 0.1091 (2) | 0.25334 (14) | 0.0394 (4) | |
H12A | 0.5360 | 0.0190 | 0.2762 | 0.059* | |
H12B | 0.5757 | 0.1105 | 0.1695 | 0.059* | |
H12C | 0.5100 | 0.1642 | 0.2820 | 0.059* | |
C13 | 0.7628 (2) | −0.20286 (16) | 0.40713 (14) | 0.0354 (4) | |
H13A | 0.8643 | −0.2026 | 0.4488 | 0.053* | |
H13B | 0.7465 | −0.2639 | 0.3403 | 0.053* | |
H13C | 0.6748 | −0.2303 | 0.4577 | 0.053* | |
C14 | 1.27708 (16) | 0.28093 (14) | 0.96606 (11) | 0.0185 (3) | |
C15 | 1.29400 (17) | 0.39505 (14) | 0.90645 (11) | 0.0207 (3) | |
C16 | 1.43893 (18) | 0.44820 (15) | 0.85927 (12) | 0.0258 (3) | |
H16 | 1.4522 | 0.5250 | 0.8167 | 0.031* | |
C17 | 1.56401 (18) | 0.38788 (17) | 0.87504 (13) | 0.0302 (4) | |
H17 | 1.6636 | 0.4252 | 0.8440 | 0.036* | |
C18 | 1.54665 (18) | 0.27456 (17) | 0.93495 (13) | 0.0294 (3) | |
H18 | 1.6336 | 0.2347 | 0.9453 | 0.035* | |
C19 | 1.40069 (17) | 0.21988 (15) | 0.97969 (12) | 0.0237 (3) | |
H19 | 1.3861 | 0.1409 | 1.0194 | 0.028* | |
C20 | 1.1700 (2) | 0.55440 (16) | 0.82719 (16) | 0.0380 (4) | |
H20A | 1.2536 | 0.6296 | 0.8585 | 0.057* | |
H20B | 1.0666 | 0.5774 | 0.8240 | 0.057* | |
H20C | 1.1947 | 0.5305 | 0.7498 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02592 (19) | 0.0233 (2) | 0.01559 (18) | 0.00255 (14) | −0.00210 (13) | 0.00064 (13) |
O1 | 0.0882 (10) | 0.0284 (7) | 0.0253 (6) | 0.0323 (7) | 0.0050 (6) | 0.0065 (5) |
O2 | 0.0211 (5) | 0.0317 (6) | 0.0138 (5) | 0.0047 (4) | 0.0009 (4) | 0.0054 (4) |
O3 | 0.0389 (6) | 0.0217 (6) | 0.0171 (5) | 0.0057 (5) | 0.0037 (4) | −0.0024 (4) |
O4 | 0.0298 (5) | 0.0184 (5) | 0.0309 (6) | 0.0082 (4) | −0.0018 (4) | 0.0057 (4) |
N1 | 0.0227 (6) | 0.0228 (6) | 0.0144 (5) | 0.0052 (5) | −0.0009 (4) | 0.0003 (5) |
N2 | 0.0222 (6) | 0.0225 (6) | 0.0127 (5) | 0.0041 (5) | 0.0015 (5) | 0.0018 (5) |
N3 | 0.0208 (6) | 0.0175 (6) | 0.0142 (5) | 0.0037 (5) | 0.0006 (4) | 0.0023 (4) |
C1 | 0.0221 (7) | 0.0161 (7) | 0.0176 (7) | 0.0044 (5) | −0.0002 (5) | 0.0017 (5) |
C2 | 0.0246 (7) | 0.0165 (7) | 0.0161 (6) | 0.0077 (5) | 0.0013 (5) | 0.0033 (5) |
C3 | 0.0243 (7) | 0.0221 (7) | 0.0159 (6) | 0.0042 (6) | 0.0014 (5) | 0.0018 (5) |
C4 | 0.0248 (7) | 0.0220 (7) | 0.0160 (6) | 0.0037 (6) | 0.0008 (5) | 0.0010 (5) |
C5 | 0.0194 (7) | 0.0230 (7) | 0.0161 (6) | 0.0037 (5) | 0.0004 (5) | 0.0012 (5) |
C6 | 0.0397 (9) | 0.0234 (8) | 0.0189 (7) | 0.0115 (7) | 0.0018 (6) | −0.0031 (6) |
C7 | 0.0382 (8) | 0.0227 (8) | 0.0226 (7) | 0.0131 (6) | 0.0026 (6) | 0.0051 (6) |
C8 | 0.0208 (7) | 0.0267 (8) | 0.0134 (6) | 0.0068 (6) | 0.0013 (5) | 0.0031 (5) |
C9 | 0.0193 (6) | 0.0211 (7) | 0.0165 (6) | 0.0031 (5) | 0.0023 (5) | −0.0021 (5) |
C10 | 0.0225 (7) | 0.0186 (7) | 0.0183 (7) | 0.0044 (5) | 0.0008 (5) | 0.0023 (5) |
C11 | 0.152 (3) | 0.0320 (11) | 0.0399 (11) | 0.0512 (15) | 0.0137 (13) | 0.0079 (9) |
C12 | 0.0228 (8) | 0.0672 (13) | 0.0262 (8) | 0.0064 (8) | −0.0028 (6) | 0.0151 (8) |
C13 | 0.0555 (11) | 0.0198 (8) | 0.0284 (8) | 0.0029 (7) | 0.0116 (7) | −0.0035 (6) |
C14 | 0.0196 (6) | 0.0197 (7) | 0.0151 (6) | 0.0027 (5) | 0.0008 (5) | −0.0015 (5) |
C15 | 0.0243 (7) | 0.0188 (7) | 0.0175 (6) | 0.0032 (6) | −0.0008 (5) | −0.0016 (5) |
C16 | 0.0319 (8) | 0.0233 (8) | 0.0178 (7) | −0.0023 (6) | 0.0035 (6) | 0.0003 (6) |
C17 | 0.0237 (7) | 0.0374 (9) | 0.0245 (7) | −0.0022 (6) | 0.0072 (6) | −0.0076 (7) |
C18 | 0.0233 (7) | 0.0361 (9) | 0.0300 (8) | 0.0113 (7) | 0.0006 (6) | −0.0083 (7) |
C19 | 0.0280 (7) | 0.0219 (8) | 0.0218 (7) | 0.0084 (6) | −0.0006 (6) | −0.0015 (6) |
C20 | 0.0477 (10) | 0.0211 (8) | 0.0438 (10) | 0.0067 (7) | −0.0093 (8) | 0.0116 (7) |
S1—C2 | 1.6775 (14) | C7—C8 | 1.393 (2) |
O1—C7 | 1.3650 (18) | C8—C9 | 1.390 (2) |
O1—C11 | 1.435 (2) | C9—C10 | 1.3944 (19) |
O2—C8 | 1.3826 (15) | C10—H10 | 0.9500 |
O2—C12 | 1.4397 (18) | C11—H11A | 0.9800 |
O3—C9 | 1.3647 (17) | C11—H11B | 0.9800 |
O3—C13 | 1.4309 (19) | C11—H11C | 0.9800 |
O4—C15 | 1.3642 (17) | C12—H12A | 0.9800 |
O4—C20 | 1.4324 (18) | C12—H12B | 0.9800 |
N1—C1 | 1.2987 (19) | C12—H12C | 0.9800 |
N1—N2 | 1.3861 (15) | C13—H13A | 0.9800 |
N2—C2 | 1.3326 (19) | C13—H13B | 0.9800 |
N2—H2N | 0.878 (17) | C13—H13C | 0.9800 |
N3—C2 | 1.3778 (17) | C14—C19 | 1.3792 (19) |
N3—C1 | 1.3789 (18) | C14—C15 | 1.389 (2) |
N3—C14 | 1.4340 (18) | C15—C16 | 1.391 (2) |
C1—C3 | 1.4892 (18) | C16—C17 | 1.388 (2) |
C3—C4 | 1.5266 (19) | C16—H16 | 0.9500 |
C3—H3A | 0.9900 | C17—C18 | 1.384 (2) |
C3—H3B | 0.9900 | C17—H17 | 0.9500 |
C4—C5 | 1.5122 (18) | C18—C19 | 1.389 (2) |
C4—H4A | 0.9900 | C18—H18 | 0.9500 |
C4—H4B | 0.9900 | C19—H19 | 0.9500 |
C5—C10 | 1.3859 (19) | C20—H20A | 0.9800 |
C5—C6 | 1.389 (2) | C20—H20B | 0.9800 |
C6—C7 | 1.391 (2) | C20—H20C | 0.9800 |
C6—H6 | 0.9500 | ||
C7—O1—C11 | 116.44 (13) | C5—C10—H10 | 120.3 |
C8—O2—C12 | 113.01 (11) | C9—C10—H10 | 120.3 |
C9—O3—C13 | 116.17 (11) | O1—C11—H11A | 109.5 |
C15—O4—C20 | 117.11 (12) | O1—C11—H11B | 109.5 |
C1—N1—N2 | 103.56 (11) | H11A—C11—H11B | 109.5 |
C2—N2—N1 | 113.78 (11) | O1—C11—H11C | 109.5 |
C2—N2—H2N | 125.4 (11) | H11A—C11—H11C | 109.5 |
N1—N2—H2N | 119.5 (11) | H11B—C11—H11C | 109.5 |
C2—N3—C1 | 107.91 (12) | O2—C12—H12A | 109.5 |
C2—N3—C14 | 126.41 (11) | O2—C12—H12B | 109.5 |
C1—N3—C14 | 125.68 (11) | H12A—C12—H12B | 109.5 |
N1—C1—N3 | 111.33 (12) | O2—C12—H12C | 109.5 |
N1—C1—C3 | 126.51 (12) | H12A—C12—H12C | 109.5 |
N3—C1—C3 | 122.13 (12) | H12B—C12—H12C | 109.5 |
N2—C2—N3 | 103.34 (11) | O3—C13—H13A | 109.5 |
N2—C2—S1 | 128.07 (11) | O3—C13—H13B | 109.5 |
N3—C2—S1 | 128.58 (11) | H13A—C13—H13B | 109.5 |
C1—C3—C4 | 112.98 (12) | O3—C13—H13C | 109.5 |
C1—C3—H3A | 109.0 | H13A—C13—H13C | 109.5 |
C4—C3—H3A | 109.0 | H13B—C13—H13C | 109.5 |
C1—C3—H3B | 109.0 | C19—C14—C15 | 121.49 (13) |
C4—C3—H3B | 109.0 | C19—C14—N3 | 119.04 (13) |
H3A—C3—H3B | 107.8 | C15—C14—N3 | 119.47 (12) |
C5—C4—C3 | 111.07 (12) | O4—C15—C14 | 115.78 (12) |
C5—C4—H4A | 109.4 | O4—C15—C16 | 125.22 (13) |
C3—C4—H4A | 109.4 | C14—C15—C16 | 118.99 (13) |
C5—C4—H4B | 109.4 | C17—C16—C15 | 119.34 (14) |
C3—C4—H4B | 109.4 | C17—C16—H16 | 120.3 |
H4A—C4—H4B | 108.0 | C15—C16—H16 | 120.3 |
C10—C5—C6 | 120.43 (13) | C18—C17—C16 | 121.38 (14) |
C10—C5—C4 | 120.11 (13) | C18—C17—H17 | 119.3 |
C6—C5—C4 | 119.45 (12) | C16—C17—H17 | 119.3 |
C5—C6—C7 | 120.17 (13) | C17—C18—C19 | 119.21 (14) |
C5—C6—H6 | 119.9 | C17—C18—H18 | 120.4 |
C7—C6—H6 | 119.9 | C19—C18—H18 | 120.4 |
O1—C7—C6 | 125.01 (14) | C14—C19—C18 | 119.55 (14) |
O1—C7—C8 | 115.33 (13) | C14—C19—H19 | 120.2 |
C6—C7—C8 | 119.65 (14) | C18—C19—H19 | 120.2 |
O2—C8—C9 | 120.15 (12) | O4—C20—H20A | 109.5 |
O2—C8—C7 | 119.89 (13) | O4—C20—H20B | 109.5 |
C9—C8—C7 | 119.96 (12) | H20A—C20—H20B | 109.5 |
O3—C9—C8 | 115.17 (12) | O4—C20—H20C | 109.5 |
O3—C9—C10 | 124.48 (13) | H20A—C20—H20C | 109.5 |
C8—C9—C10 | 120.34 (13) | H20B—C20—H20C | 109.5 |
C5—C10—C9 | 119.45 (13) | ||
C1—N1—N2—C2 | 1.85 (15) | C6—C7—C8—C9 | −0.4 (2) |
N2—N1—C1—N3 | −0.12 (15) | C13—O3—C9—C8 | −172.13 (13) |
N2—N1—C1—C3 | −178.15 (13) | C13—O3—C9—C10 | 6.8 (2) |
C2—N3—C1—N1 | −1.52 (16) | O2—C8—C9—O3 | −1.54 (19) |
C14—N3—C1—N1 | 178.47 (12) | C7—C8—C9—O3 | 178.61 (13) |
C2—N3—C1—C3 | 176.61 (12) | O2—C8—C9—C10 | 179.45 (12) |
C14—N3—C1—C3 | −3.4 (2) | C7—C8—C9—C10 | −0.4 (2) |
N1—N2—C2—N3 | −2.71 (15) | C6—C5—C10—C9 | −0.7 (2) |
N1—N2—C2—S1 | 176.30 (10) | C4—C5—C10—C9 | 179.49 (12) |
C1—N3—C2—N2 | 2.48 (14) | O3—C9—C10—C5 | −177.96 (13) |
C14—N3—C2—N2 | −177.52 (12) | C8—C9—C10—C5 | 1.0 (2) |
C1—N3—C2—S1 | −176.53 (11) | C2—N3—C14—C19 | 72.32 (18) |
C14—N3—C2—S1 | 3.5 (2) | C1—N3—C14—C19 | −107.68 (15) |
N1—C1—C3—C4 | 0.6 (2) | C2—N3—C14—C15 | −107.91 (15) |
N3—C1—C3—C4 | −177.23 (12) | C1—N3—C14—C15 | 72.09 (18) |
C1—C3—C4—C5 | 166.39 (11) | C20—O4—C15—C14 | −172.91 (13) |
C3—C4—C5—C10 | 104.08 (15) | C20—O4—C15—C16 | 6.9 (2) |
C3—C4—C5—C6 | −75.69 (17) | C19—C14—C15—O4 | −179.94 (12) |
C10—C5—C6—C7 | 0.0 (2) | N3—C14—C15—O4 | 0.29 (18) |
C4—C5—C6—C7 | 179.76 (14) | C19—C14—C15—C16 | 0.2 (2) |
C11—O1—C7—C6 | 3.6 (3) | N3—C14—C15—C16 | −179.52 (12) |
C11—O1—C7—C8 | −177.92 (19) | O4—C15—C16—C17 | 178.73 (13) |
C5—C6—C7—O1 | 178.94 (15) | C14—C15—C16—C17 | −1.5 (2) |
C5—C6—C7—C8 | 0.6 (2) | C15—C16—C17—C18 | 1.2 (2) |
C12—O2—C8—C9 | 82.37 (17) | C16—C17—C18—C19 | 0.3 (2) |
C12—O2—C8—C7 | −97.78 (17) | C15—C14—C19—C18 | 1.3 (2) |
O1—C7—C8—O2 | 1.3 (2) | N3—C14—C19—C18 | −178.96 (12) |
C6—C7—C8—O2 | 179.79 (13) | C17—C18—C19—C14 | −1.5 (2) |
O1—C7—C8—C9 | −178.88 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2i | 0.878 (17) | 1.890 (18) | 2.7558 (15) | 168.4 (15) |
Symmetry code: (i) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H23N3O4S |
Mr | 401.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 8.6368 (6), 10.5422 (7), 11.6944 (8) |
α, β, γ (°) | 91.733 (1), 92.955 (1), 104.075 (1) |
V (Å3) | 1030.44 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.55 × 0.35 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Integration (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.926, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8266, 4149, 3689 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.099, 1.07 |
No. of reflections | 4149 |
No. of parameters | 261 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.25 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···O2i | 0.878 (17) | 1.890 (18) | 2.7558 (15) | 168.4 (15) |
Symmetry code: (i) x, y, z+1. |
Acknowledgements
The authors gratefully acknowledge funds from the Higher Education Commission, Islamabad, Pakistan.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Substituted triazole derivatives display significant biological activities including antimicrobial (Holla et al., 1998), analgesic (Turan-Zitouni et al., 1999), antitumor (Demirbas et al., 2002), antihypertensive (Paulvannan et al., 2000) and antiviral activities (Kritsanida et al., 2002). The biological activity is closely related to the structure, possibly being due to the presence of the —N—C ?S unit (Omar et al., 1986). We are interested in the synthesis and biological activities of aryloxyacetyl hydrazide derivatives and report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987), and are comparable with those observed in related structures Öztürk et al., 2004a,b). The C2?S1 [1.6775 (14) Å] bond is in accordance with the corresponding values of 1.6773 (19) Å in 4-(4-chlorophenyl)-3-(furan-2-yl)-1H-1,2,4-triazole-5(4H)-thione Öztürk et al., 2004a) and 1.668 (5) Å in 4-amino-3-(1,2,3,4,5-pentahydroxypentyl)-1H-1,2,4-triazole-5(4H)-thione (Zhang et al., 2004). In the triazole ring, the N2 ?C2 [1.3326 (19) Å] bond shows double-bond character.
The rings A (N1–N3/C1/C2), B (C5–C10) and C (C14–C19) are, of course, planar and dihedral angles between them are A/B = 78.60 (3)°, A/C = 71.57 (3)° and B/C = 74.12 (3)°.
In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the c axis (Fig. 2), in which they may be effective in the stabilization of the structure.