Literature DB >> 21579734

1-Benzoyl-methyl-3-(2-thienylmeth-yl)-4-(2-thienylmethyl-eneamino)-1H-1,2,4-triazol-5(4H)-one.

Hasan Tanak, Metin Yavuz, Zeliha Lagap, Orhan Büyükgüngör.   

Abstract

In the title compound, C(20)H(16)N(4)O(2)S(2), one of the thio-phene rings is disordered [occupancy ratio 0.710 (4):0.290 (4)] and the disorder is of the flip type. An intra-molecular C-H⋯O hydrogen bond generates a six-membered ring with an S(6) motif.

Entities:  

Year:  2010        PMID： 21579734      PMCID： PMC2979876          DOI： 10.1107/S160053681000005X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to 1,2,4-triazoles and thio­phenes, see: Santen (2003 ▶); Clemons et al. (2004 ▶); Chen et al. (1997 ▶); Mohareb et al. (2004 ▶); Collin et al. (2003 ▶). For the graph-set description of hydrogen bonds, see: Bernstein et al. (1995 ▶). For reference structural data, see: Allen et al. (1987 ▶). For related structures, see: Tanak et al. (2009 ▶); Akkurt et al. (2008 ▶); Ustabaş et al. (2009 ▶).

Experimental

Crystal data

C20H16N4O2S2 M = 408.49 Monoclinic, a = 25.287 (3) Å b = 5.5347 (4) Å c = 28.281 (2) Å β = 102.430 (7)° V = 3865.2 (6) Å3 Z = 8 Mo Kα radiation μ = 0.30 mm−1 T = 296 K 0.80 × 0.37 × 0.14 mm

Data collection

Stoe IPDS II diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.776, T max = 0.913 20676 measured reflections 3865 independent reflections 2676 reflections with I > 2σ(I) R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.141 S = 1.05 3865 reflections 272 parameters 104 restraints H-atom parameters constrained Δρmax = 0.36 e Å−3 Δρmin = −0.31 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000005X/dn2520sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681000005X/dn2520Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H16N4O2S2F(000) = 1696
Mr = 408.49Dx = 1.404 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5214 reflections
a = 25.287 (3) Åθ = 1.5–26.6°
b = 5.5347 (4) ŵ = 0.30 mm−1
c = 28.281 (2) ÅT = 296 K
β = 102.430 (7)°Needle, colorless
V = 3865.2 (6) Å30.80 × 0.37 × 0.14 mm
Z = 8
Stoe IPDS II diffractometer3865 independent reflections
Radiation source: fine-focus sealed tube2676 reflections with I > 2σ(I)
graphiteRint = 0.037
Detector resolution: 6.67 pixels mm-1θmax = 26.2°, θmin = 1.5°
rotation method scansh = −30→31
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −6→6
Tmin = 0.776, Tmax = 0.913l = −34→34
20676 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0757P)2 + 0.8966P] where P = (Fo2 + 2Fc2)/3
3865 reflections(Δ/σ)max = 0.001
272 parametersΔρmax = 0.36 e Å−3
104 restraintsΔρmin = −0.31 e Å−3
Experimental. 281 frames, detector distance = 125 mm
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.
xyzUiso*/UeqOcc. (<1)
S10.47605 (4)0.54631 (18)0.68233 (3)0.0833 (3)
O10.53985 (8)0.2178 (4)0.51294 (7)0.0694 (6)
O20.67029 (9)0.1247 (4)0.51864 (8)0.0801 (7)
N10.61243 (9)−0.1968 (5)0.59495 (8)0.0610 (6)
N20.59159 (9)−0.1102 (5)0.54847 (8)0.0591 (6)
N30.56138 (8)0.1266 (4)0.59653 (7)0.0550 (5)
N40.53290 (9)0.2812 (4)0.61947 (8)0.0567 (6)
C10.59244 (10)−0.0525 (5)0.62262 (9)0.0571 (7)
C20.56182 (10)0.0935 (5)0.54744 (9)0.0565 (7)
C30.61089 (11)−0.2103 (5)0.50850 (10)0.0595 (7)
H3A0.5814−0.21610.48020.071*
H3B0.6232−0.37440.51630.071*
C40.65705 (11)−0.0615 (5)0.49698 (9)0.0558 (6)
C50.68400 (10)−0.1502 (5)0.45852 (9)0.0529 (6)
C60.66851 (13)−0.3618 (6)0.43283 (10)0.0678 (8)
H60.6405−0.45480.43970.081*
C70.69452 (16)−0.4339 (7)0.39723 (12)0.0829 (10)
H70.6836−0.57390.37970.099*
C80.73677 (16)−0.2991 (8)0.38754 (13)0.0869 (11)
H80.7543−0.34830.36340.104*
C90.75304 (14)−0.0933 (7)0.41332 (12)0.0796 (9)
H90.7821−0.00490.40720.096*
C100.72666 (12)−0.0170 (6)0.44804 (10)0.0643 (7)
H100.73740.12550.46480.077*
C110.50618 (10)0.4552 (5)0.59640 (9)0.0551 (6)
H110.50610.48360.56400.066*
C120.47593 (11)0.6068 (5)0.62279 (9)0.0572 (7)
C130.44447 (12)0.8073 (6)0.60642 (11)0.0672 (7)
H130.43920.86810.57510.081*
C140.42152 (15)0.9073 (7)0.64294 (13)0.0836 (9)
H140.39911.04240.63860.100*
C150.43555 (16)0.7853 (7)0.68508 (13)0.0888 (11)
H150.42400.82880.71300.107*
C160.60269 (12)−0.0648 (6)0.67632 (9)0.0678 (8)
H16A0.6191−0.21920.68700.081*
H16B0.5684−0.05570.68630.081*
C170.63885 (11)0.1337 (6)0.70048 (8)0.0683 (7)
S2A0.63477 (7)0.2526 (3)0.75375 (5)0.1001 (6)0.710 (4)
C18A0.6783 (3)0.2503 (12)0.6854 (3)0.0779 (12)0.710 (4)
H18A0.68780.21470.65620.094*0.710 (4)
S2B0.68795 (15)0.2524 (8)0.67823 (15)0.0812 (11)0.290 (4)
C18B0.6385 (3)0.2512 (14)0.7420 (3)0.0910 (15)0.290 (4)
H18B0.61380.21690.76120.109*0.290 (4)
C190.70600 (12)0.4412 (6)0.71870 (13)0.0940 (9)
H190.73470.53820.71460.113*
C200.68156 (14)0.4441 (6)0.75479 (11)0.0973 (9)
H200.69120.55380.78010.117*
U11U22U33U12U13U23
S10.1088 (7)0.0827 (6)0.0612 (4)0.0136 (5)0.0245 (4)0.0073 (4)
O10.0786 (13)0.0740 (14)0.0515 (10)0.0032 (11)0.0049 (9)0.0091 (10)
O20.0878 (15)0.0773 (15)0.0819 (14)−0.0314 (12)0.0330 (11)−0.0300 (12)
N10.0583 (13)0.0669 (15)0.0587 (13)−0.0020 (12)0.0145 (10)0.0141 (11)
N20.0570 (12)0.0669 (16)0.0543 (12)−0.0012 (12)0.0137 (10)0.0077 (11)
N30.0526 (12)0.0623 (14)0.0506 (11)0.0002 (11)0.0121 (9)0.0091 (10)
N40.0554 (12)0.0611 (14)0.0540 (12)−0.0021 (11)0.0126 (10)0.0055 (11)
C10.0520 (14)0.0639 (17)0.0562 (14)−0.0048 (13)0.0134 (11)0.0122 (13)
C20.0504 (14)0.0640 (18)0.0543 (14)−0.0087 (13)0.0094 (11)0.0054 (13)
C30.0612 (16)0.0599 (17)0.0571 (14)−0.0074 (13)0.0119 (12)−0.0024 (12)
C40.0573 (15)0.0559 (17)0.0522 (13)−0.0077 (13)0.0072 (11)−0.0023 (12)
C50.0546 (14)0.0545 (16)0.0471 (12)0.0000 (12)0.0053 (10)0.0021 (11)
C60.0774 (19)0.0589 (18)0.0657 (16)−0.0015 (15)0.0125 (14)−0.0050 (14)
C70.108 (3)0.067 (2)0.0728 (19)0.011 (2)0.0178 (18)−0.0160 (16)
C80.100 (3)0.094 (3)0.074 (2)0.024 (2)0.0341 (19)−0.0010 (19)
C90.077 (2)0.095 (3)0.0724 (19)−0.0003 (19)0.0278 (16)0.0074 (19)
C100.0690 (17)0.0680 (19)0.0562 (15)−0.0079 (15)0.0138 (13)−0.0014 (13)
C110.0527 (14)0.0605 (17)0.0503 (13)−0.0115 (13)0.0075 (11)0.0025 (12)
C120.0587 (15)0.0571 (17)0.0533 (14)−0.0084 (13)0.0064 (11)0.0009 (12)
C130.0761 (18)0.0598 (17)0.0629 (15)−0.0033 (15)0.0093 (13)−0.0005 (13)
C140.093 (2)0.068 (2)0.087 (2)0.0115 (17)0.0130 (17)−0.0029 (17)
C150.109 (3)0.086 (3)0.077 (2)0.009 (2)0.0300 (19)−0.0089 (19)
C160.0717 (18)0.074 (2)0.0597 (15)0.0011 (16)0.0176 (13)0.0214 (14)
C170.0726 (15)0.0800 (16)0.0527 (12)0.0032 (13)0.0144 (11)0.0140 (12)
S2A0.1227 (11)0.1241 (12)0.0609 (8)−0.0224 (9)0.0364 (7)−0.0061 (7)
C18A0.079 (2)0.092 (2)0.071 (2)−0.005 (2)0.0339 (18)0.0026 (18)
S2B0.0736 (18)0.0932 (19)0.0825 (18)−0.0038 (15)0.0292 (14)0.0002 (14)
C18B0.107 (3)0.104 (3)0.065 (3)−0.010 (2)0.025 (2)−0.001 (2)
C190.0851 (18)0.0907 (19)0.1016 (19)−0.0082 (16)0.0097 (15)0.0082 (16)
C200.119 (2)0.097 (2)0.0682 (16)−0.0077 (17)0.0020 (16)0.0006 (15)
S1—C151.685 (4)C9—H90.9300
S1—C121.716 (3)C10—H100.9300
O1—C21.225 (3)C11—C121.446 (4)
O2—C41.209 (3)C11—H110.9300
N1—C11.294 (4)C12—C131.386 (4)
N1—N21.392 (3)C13—C141.403 (5)
N2—C21.352 (4)C13—H130.9300
N2—C31.435 (4)C14—C151.349 (5)
N3—N41.369 (3)C14—H140.9300
N3—C11.376 (4)C15—H150.9300
N3—C21.403 (3)C16—C171.497 (5)
N4—C111.273 (3)C16—H16A0.9700
C1—C161.486 (4)C16—H16B0.9700
C3—C41.520 (4)C17—C18A1.333 (8)
C3—H3A0.9700C17—C18B1.344 (9)
C3—H3B0.9700C17—S2B1.645 (4)
C4—C51.486 (4)C17—S2A1.668 (3)
C5—C61.389 (4)S2A—C201.584 (4)
C5—C101.390 (4)C18A—C191.487 (10)
C6—C71.375 (5)C18A—H18A0.9300
C6—H60.9300S2B—C191.545 (5)
C7—C81.378 (5)C18B—C201.512 (10)
C7—H70.9300C18B—H18B0.9300
C8—C91.367 (5)C19—C201.302 (6)
C8—H80.9300C19—H190.9300
C9—C101.367 (4)C20—H200.9300
C15—S1—C1291.12 (17)C13—C12—C11128.4 (2)
C1—N1—N2103.9 (2)C13—C12—S1111.3 (2)
C2—N2—N1113.8 (2)C11—C12—S1120.2 (2)
C2—N2—C3125.9 (2)C12—C13—C14111.6 (3)
N1—N2—C3119.1 (2)C12—C13—H13124.2
N4—N3—C1119.6 (2)C14—C13—H13124.2
N4—N3—C2131.9 (2)C15—C14—C13112.4 (3)
C1—N3—C2108.2 (2)C15—C14—H14123.8
C11—N4—N3120.4 (2)C13—C14—H14123.8
N1—C1—N3111.9 (2)C14—C15—S1113.5 (3)
N1—C1—C16125.8 (3)C14—C15—H15123.2
N3—C1—C16122.3 (3)S1—C15—H15123.2
O1—C2—N2129.8 (3)C1—C16—C17112.8 (2)
O1—C2—N3128.0 (3)C1—C16—H16A109.0
N2—C2—N3102.1 (2)C17—C16—H16A109.0
N2—C3—C4111.5 (2)C1—C16—H16B109.0
N2—C3—H3A109.3C17—C16—H16B109.0
C4—C3—H3A109.3H16A—C16—H16B107.8
N2—C3—H3B109.3C18A—C17—C18B101.1 (8)
C4—C3—H3B109.3C18A—C17—C16129.4 (4)
H3A—C3—H3B108.0C18B—C17—C16129.4 (5)
O2—C4—C5122.1 (3)C18B—C17—S2B106.8 (4)
O2—C4—C3119.7 (3)C16—C17—S2B123.8 (2)
C5—C4—C3118.2 (2)C18A—C17—S2A107.1 (4)
C6—C5—C10118.7 (3)C16—C17—S2A123.47 (19)
C6—C5—C4122.6 (3)S2B—C17—S2A112.7 (3)
C10—C5—C4118.7 (2)C20—S2A—C1795.14 (19)
C7—C6—C5120.1 (3)C17—C18A—C19115.1 (6)
C7—C6—H6119.9C17—C18A—H18A122.5
C5—C6—H6119.9C19—C18A—H18A122.5
C6—C7—C8120.1 (3)C19—S2B—C1796.5 (2)
C6—C7—H7119.9C17—C18B—C20114.2 (7)
C8—C7—H7119.9C17—C18B—H18B122.9
C9—C8—C7120.1 (3)C20—C18B—H18B122.9
C9—C8—H8119.9C20—C19—C18A105.5 (4)
C7—C8—H8119.9C20—C19—S2B118.3 (2)
C10—C9—C8120.2 (3)C20—C19—H19127.3
C10—C9—H9119.9C18A—C19—H19127.3
C8—C9—H9119.9S2B—C19—H19114.4
C9—C10—C5120.7 (3)C19—C20—C18B104.1 (4)
C9—C10—H10119.7C19—C20—S2A117.1 (2)
C5—C10—H10119.7C19—C20—H20121.4
N4—C11—C12117.1 (2)C18B—C20—H20134.4
N4—C11—H11121.4S2A—C20—H20121.4
C12—C11—H11121.4
C1—N1—N2—C23.8 (3)C11—C12—C13—C14−179.8 (3)
C1—N1—N2—C3172.3 (2)S1—C12—C13—C140.3 (3)
C1—N3—N4—C11176.5 (2)C12—C13—C14—C150.1 (4)
C2—N3—N4—C11−11.2 (4)C13—C14—C15—S1−0.5 (4)
N2—N1—C1—N3−2.0 (3)C12—S1—C15—C140.6 (3)
N2—N1—C1—C16−179.3 (3)N1—C1—C16—C17107.3 (3)
N4—N3—C1—N1173.8 (2)N3—C1—C16—C17−69.8 (3)
C2—N3—C1—N1−0.2 (3)C1—C16—C17—C18A−29.9 (4)
N4—N3—C1—C16−8.8 (4)C1—C16—C17—C18B146.2 (2)
C2—N3—C1—C16177.2 (2)C1—C16—C17—S2B−32.7 (4)
N1—N2—C2—O1177.2 (3)C1—C16—C17—S2A149.2 (2)
C3—N2—C2—O19.5 (5)C18A—C17—S2A—C200.72 (9)
N1—N2—C2—N3−3.8 (3)C18B—C17—S2A—C20−19 (2)
C3—N2—C2—N3−171.4 (2)C16—C17—S2A—C20−178.5 (3)
N4—N3—C2—O18.5 (5)S2B—C17—S2A—C203.2 (2)
C1—N3—C2—O1−178.6 (3)C18B—C17—C18A—C192.5 (2)
N4—N3—C2—N2−170.6 (2)C16—C17—C18A—C19179.5 (3)
C1—N3—C2—N22.4 (3)S2B—C17—C18A—C19−158 (2)
C2—N2—C3—C472.9 (3)S2A—C17—C18A—C190.31 (12)
N1—N2—C3—C4−94.1 (3)C18A—C17—S2B—C1919 (2)
N2—C3—C4—O2−4.8 (4)C18B—C17—S2B—C19−0.80 (10)
N2—C3—C4—C5176.1 (2)C16—C17—S2B—C19178.3 (3)
O2—C4—C5—C6−178.9 (3)S2A—C17—S2B—C19−3.4 (2)
C3—C4—C5—C60.3 (4)C18A—C17—C18B—C20−2.7 (2)
O2—C4—C5—C101.6 (4)C16—C17—C18B—C20−179.6 (3)
C3—C4—C5—C10−179.3 (2)S2B—C17—C18B—C20−0.60 (12)
C10—C5—C6—C7−1.1 (4)S2A—C17—C18B—C20158 (2)
C4—C5—C6—C7179.3 (3)C17—C18A—C19—C20−1.4 (2)
C5—C6—C7—C81.3 (5)C17—C18A—C19—S2B169.1 (9)
C6—C7—C8—C90.1 (5)C17—S2B—C19—C202.3 (2)
C7—C8—C9—C10−1.6 (5)C17—S2B—C19—C18A−8.0 (7)
C8—C9—C10—C51.7 (5)C18A—C19—C20—C18B−0.31 (17)
C6—C5—C10—C9−0.3 (4)S2B—C19—C20—C18B−2.7 (3)
C4—C5—C10—C9179.2 (3)C18A—C19—C20—S2A2.0 (3)
N3—N4—C11—C12178.4 (2)S2B—C19—C20—S2A−0.4 (2)
N4—C11—C12—C13179.1 (3)C17—C18B—C20—C192.0 (2)
N4—C11—C12—S1−1.1 (3)C17—C18B—C20—S2A−168.8 (9)
C15—S1—C12—C13−0.5 (2)C17—S2A—C20—C19−1.8 (2)
C15—S1—C12—C11179.6 (2)C17—S2A—C20—C18B8.2 (7)
D—H···AD—HH···AD···AD—H···A
C11—H11···O10.932.352.981 (3)125
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C11—H11⋯O10.932.352.981 (3)125
  7 in total

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Journal:  Steroids       Date:  2003-09       Impact factor: 2.668

6.  2-Benzoylmethyl-4-[(2-benzylidene-ethylidene)amino]-5-(2-thienylmethyl)-2H-1,2,4-triazol-3(4H)-one.

Authors:  Reşat Ustabaş; Yasemin Unver; Nevin Suleymanoğlu; Ufuk Coruh; Kemal Sancak
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-04-08

7.  4-(2,3-Dihydroxybenzyl-ideneamino)-3-methyl-1H-1,2,4-triazol-5(4H)-one.

Authors:  Hasan Tanak; Yavuz Köysal; Metin Yavuz; Samil Işık; Gülşah Gül
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-11-07
  7 in total

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