Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Jan 30;66(Pt 2):o488. doi: 10.1107/S1600536810003181

5-Phenyl-3-(2-thien­yl)-1,2,4-triazolo[3,4-a]isoquinoline

F Nawaz Khan a, P Manivel a, K Prabakaran a, Venkatesha R Hathwar b, Seik Weng Ng c,*
PMCID: PMC2979772  PMID: 21579895

Abstract

In the title mol­ecule, C20H13N3S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.045 Å and a maximum deviation of 0.090 (2) Å from the mean plane for the triazole ring C atom which is bonded to the thio­phene ring. The phenyl ring is twisted by 52.0 (1)° with respect to the mean plane of the triazoloisoquinoline ring system. The thio­phene ring is rotationally disordered by approximately 180° over two sites, the ratio of refined occupancies being 0.73 (1):0.27 (1).

Related literature

For the synthesis and anti­helmintic activity of triazolo compounds similar to the title compound, see: Nadkarni et al. (2001 ▶).graphic file with name e-66-0o488-scheme1.jpg

Experimental

Crystal data

  • C20H13N3S

  • M r = 327.39

  • Orthorhombic, Inline graphic

  • a = 19.7715 (17) Å

  • b = 8.7735 (7) Å

  • c = 9.3027 (8) Å

  • V = 1613.7 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 293 K

  • 0.32 × 0.30 × 0.24 mm

Data collection

  • Bruker SMART area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.952

  • 10809 measured reflections

  • 3670 independent reflections

  • 2414 reflections with I > 2σ(I)

  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057

  • wR(F 2) = 0.128

  • S = 1.03

  • 3670 reflections

  • 230 parameters

  • 45 restraints

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.21 e Å−3

  • Absolute structure: Flack (1983 ▶), 1631 Friedel pairs

  • Flack parameter: 0.05 (13)

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003181/lh2984sup1.cif

e-66-0o488-sup1.cif (20.3KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003181/lh2984Isup2.hkl

e-66-0o488-Isup2.hkl (180KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program; FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The molecular structure of the title compound is shown in Fig. 1.

Experimental

2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with thienyl-2-carbaldehye (1.1 mmol) under refluxing conditions isopropanol (10 ml) solvent to give the corresponding 2-(3-phenylisoquinolin-1-yl)-1-(2-thienylmethylene)hydrazine in high yield. The compound was then oxidatively cyclized in nitrobenzene (10 ml) at 473 K. The product was recrystallized from dichlomethane to give block-shaped crystals.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

The thienyl ring is disordered over two positions. The temperature factors of the primed atoms were restrained to those of the unprimed ones, and the anisotropic temperature factors were restrained to be nearly isotropic. Pairs of distances of the primed atoms were restrained to within 0.01 Å of the umprimed ones.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

Thermal ellipsoid plot (Barbour, 2001) of C20H13N3S at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

Crystal data

C20H13N3S F(000) = 680
Mr = 327.39 Dx = 1.348 Mg m−3
Orthorhombic, P21212 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab Cell parameters from 1886 reflections
a = 19.7715 (17) Å θ = 2.4–20.1°
b = 8.7735 (7) Å µ = 0.21 mm−1
c = 9.3027 (8) Å T = 293 K
V = 1613.7 (2) Å3 Block, yellow
Z = 4 0.32 × 0.30 × 0.24 mm
Open in a new tab

Data collection

Bruker SMART area-detector diffractometer 3670 independent reflections
Radiation source: fine-focus sealed tube 2414 reflections with I > 2σ(I)
graphite Rint = 0.045
φ and ω scans θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −25→25
Tmin = 0.937, Tmax = 0.952 k = −11→10
10809 measured reflections l = −10→12
Open in a new tab

Refinement

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)] = 0.057 H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0577P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max = 0.001
3670 reflections Δρmax = 0.20 e Å−3
230 parameters Δρmin = −0.21 e Å−3
45 restraints Absolute structure: Flack (1983), 1631 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.05 (13)
Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
S1 0.59650 (8) 0.46180 (17) 0.63475 (18) 0.0639 (5) 0.731 (3)
S1' 0.5970 (3) 0.1599 (5) 0.7573 (7) 0.0639 (5) 0.27
N1 0.50872 (10) 0.2300 (3) 0.3908 (2) 0.0425 (6)
N2 0.41393 (12) 0.1323 (3) 0.4794 (3) 0.0563 (7)
N3 0.45695 (12) 0.1669 (3) 0.5908 (3) 0.0555 (7)
C1 0.55374 (13) 0.2743 (3) 0.2800 (3) 0.0468 (7)
C2 0.52959 (14) 0.2706 (4) 0.1445 (3) 0.0583 (8)
H2 0.5581 0.3016 0.0707 0.070*
C3 0.46266 (14) 0.2218 (4) 0.1071 (3) 0.0563 (8)
C4 0.43864 (17) 0.2247 (5) −0.0345 (4) 0.0718 (10)
H4 0.4665 0.2600 −0.1078 0.086*
C5 0.37500 (18) 0.1765 (4) −0.0660 (4) 0.0746 (11)
H5 0.3598 0.1784 −0.1607 0.090*
C6 0.33259 (17) 0.1246 (4) 0.0419 (4) 0.0715 (10)
H6 0.2891 0.0924 0.0193 0.086*
C7 0.35420 (15) 0.1203 (4) 0.1817 (4) 0.0615 (9)
H7 0.3254 0.0858 0.2538 0.074*
C8 0.41991 (14) 0.1682 (3) 0.2156 (3) 0.0483 (7)
C9 0.44535 (13) 0.1724 (3) 0.3605 (3) 0.0449 (7)
C10 0.51257 (13) 0.2250 (3) 0.5399 (3) 0.0448 (7)
C11 0.56696 (13) 0.2788 (3) 0.6329 (3) 0.0492 (7)
C12 0.5985 (3) 0.2087 (6) 0.7424 (7) 0.0665 (19) 0.731 (3)
H12 0.5866 0.1084 0.7623 0.080* 0.731 (3)
C13 0.6458 (4) 0.2730 (7) 0.8243 (11) 0.0695 (18) 0.731 (3)
H13 0.6711 0.2269 0.8965 0.083* 0.731 (3)
C14 0.6491 (3) 0.4187 (7) 0.7808 (6) 0.0649 (19) 0.731 (3)
H14 0.6770 0.4906 0.8243 0.078* 0.731 (3)
C12' 0.5862 (10) 0.4243 (14) 0.659 (2) 0.0665 (19) 0.27
H12' 0.5619 0.5062 0.6221 0.080* 0.269 (3)
C13' 0.6415 (10) 0.447 (3) 0.740 (2) 0.0695 (18) 0.27
H13' 0.6697 0.5313 0.7463 0.083* 0.269 (3)
C14' 0.6445 (15) 0.3135 (19) 0.811 (3) 0.0649 (19) 0.27
H14B 0.6729 0.3042 0.8903 0.078* 0.269 (3)
C15 0.62471 (13) 0.3176 (3) 0.3121 (3) 0.0460 (7)
C16 0.66749 (13) 0.2237 (3) 0.3895 (3) 0.0491 (7)
H16 0.6519 0.1311 0.4251 0.059*
C17 0.73382 (14) 0.2682 (4) 0.4135 (3) 0.0565 (8)
H17 0.7625 0.2051 0.4657 0.068*
C18 0.75759 (15) 0.4039 (4) 0.3615 (4) 0.0634 (9)
H18 0.8019 0.4337 0.3797 0.076*
C19 0.71543 (15) 0.4960 (4) 0.2821 (4) 0.0659 (9)
H19 0.7315 0.5875 0.2449 0.079*
C20 0.64940 (14) 0.4525 (4) 0.2576 (3) 0.0569 (8)
H20 0.6212 0.5150 0.2036 0.068*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0616 (8) 0.0510 (8) 0.0790 (10) −0.0019 (6) −0.0066 (7) −0.0081 (7)
S1' 0.0616 (8) 0.0510 (8) 0.0790 (10) −0.0019 (6) −0.0066 (7) −0.0081 (7)
N1 0.0383 (11) 0.0443 (14) 0.0448 (14) 0.0009 (10) 0.0050 (10) 0.0028 (11)
N2 0.0483 (14) 0.0649 (16) 0.0557 (16) −0.0058 (12) 0.0043 (13) 0.0079 (13)
N3 0.0510 (14) 0.0667 (17) 0.0489 (15) −0.0028 (13) 0.0059 (12) 0.0061 (13)
C1 0.0424 (14) 0.0469 (15) 0.0511 (18) 0.0034 (13) 0.0072 (13) 0.0010 (15)
C2 0.0534 (17) 0.077 (2) 0.0448 (18) −0.0024 (16) 0.0093 (14) 0.0053 (17)
C3 0.0519 (17) 0.067 (2) 0.0497 (19) 0.0066 (15) −0.0018 (14) −0.0057 (16)
C4 0.064 (2) 0.100 (3) 0.051 (2) 0.009 (2) 0.0022 (17) −0.004 (2)
C5 0.067 (2) 0.101 (3) 0.056 (2) 0.014 (2) −0.0124 (18) −0.015 (2)
C6 0.056 (2) 0.078 (2) 0.080 (3) 0.0023 (18) −0.018 (2) −0.014 (2)
C7 0.0504 (18) 0.067 (2) 0.067 (2) −0.0026 (16) −0.0045 (15) 0.0007 (17)
C8 0.0467 (16) 0.0454 (16) 0.0529 (18) 0.0058 (13) 0.0007 (14) −0.0047 (14)
C9 0.0413 (14) 0.0432 (16) 0.0501 (17) −0.0003 (12) 0.0024 (14) 0.0033 (14)
C10 0.0472 (15) 0.0431 (16) 0.0440 (17) 0.0028 (13) 0.0045 (13) 0.0023 (14)
C11 0.0463 (15) 0.0544 (17) 0.0470 (17) 0.0081 (13) 0.0031 (13) −0.0061 (15)
C12 0.073 (3) 0.045 (3) 0.082 (4) 0.002 (3) 0.012 (3) 0.011 (3)
C13 0.054 (3) 0.091 (4) 0.064 (3) 0.015 (4) −0.004 (2) −0.002 (4)
C14 0.063 (3) 0.068 (4) 0.063 (4) 0.005 (3) −0.019 (3) −0.021 (3)
C12' 0.073 (3) 0.045 (3) 0.082 (4) 0.002 (3) 0.012 (3) 0.011 (3)
C13' 0.054 (3) 0.091 (4) 0.064 (3) 0.015 (4) −0.004 (2) −0.002 (4)
C14' 0.063 (3) 0.068 (4) 0.063 (4) 0.005 (3) −0.019 (3) −0.021 (3)
C15 0.0441 (14) 0.0470 (17) 0.0471 (17) −0.0013 (13) 0.0073 (13) −0.0016 (13)
C16 0.0470 (15) 0.0484 (16) 0.0520 (18) 0.0027 (14) 0.0057 (14) 0.0051 (14)
C17 0.0451 (15) 0.069 (2) 0.0555 (18) 0.0142 (16) 0.0029 (13) −0.0004 (17)
C18 0.0441 (17) 0.080 (2) 0.066 (2) −0.0092 (16) 0.0086 (16) −0.0034 (19)
C19 0.0613 (19) 0.063 (2) 0.074 (2) −0.0157 (17) 0.0121 (17) 0.0096 (18)
C20 0.0518 (17) 0.0544 (18) 0.064 (2) −0.0016 (15) 0.0031 (15) 0.0112 (16)
Open in a new tab

Geometric parameters (Å, °)

S1—C11 1.708 (3) C10—C11 1.459 (4)
S1—C14 1.752 (4) C11—C12 1.344 (5)
S1'—C11 1.667 (5) C11—C12' 1.355 (8)
S1'—C14' 1.717 (9) C12—C13 1.331 (6)
N1—C9 1.380 (3) C12—H12 0.9300
N1—C10 1.389 (3) C13—C14 1.342 (6)
N1—C1 1.417 (3) C13—H13 0.9300
N2—C9 1.316 (4) C14—H14 0.9300
N2—N3 1.375 (3) C12'—C13' 1.343 (8)
N3—C10 1.301 (3) C12'—H12' 0.9300
C1—C2 1.348 (4) C13'—C14' 1.342 (8)
C1—C15 1.484 (4) C13'—H13' 0.9300
C2—C3 1.434 (4) C14'—H14B 0.9300
C2—H2 0.9300 C15—C20 1.377 (4)
C3—C8 1.398 (4) C15—C16 1.383 (4)
C3—C4 1.400 (4) C16—C17 1.387 (4)
C4—C5 1.359 (5) C16—H16 0.9300
C4—H4 0.9300 C17—C18 1.368 (4)
C5—C6 1.385 (5) C17—H17 0.9300
C5—H5 0.9300 C18—C19 1.376 (4)
C6—C7 1.369 (5) C18—H18 0.9300
C6—H6 0.9300 C19—C20 1.379 (4)
C7—C8 1.402 (4) C19—H19 0.9300
C7—H7 0.9300 C20—H20 0.9300
C8—C9 1.439 (4)
C11—S1—C14 90.5 (2) C10—C11—S1' 118.2 (3)
C11—S1'—C14' 84.6 (8) C12—C11—S1 105.3 (3)
C9—N1—C10 104.0 (2) C10—C11—S1 124.2 (2)
C9—N1—C1 121.5 (2) S1'—C11—S1 117.3 (2)
C10—N1—C1 134.5 (2) C13—C12—C11 124.5 (5)
C9—N2—N3 106.4 (2) C13—C12—H12 117.8
C10—N3—N2 109.6 (2) C11—C12—H12 117.8
C2—C1—N1 116.8 (2) C12—C13—C14 105.4 (6)
C2—C1—C15 122.0 (3) C12—C13—H13 127.3
N1—C1—C15 121.2 (2) C14—C13—H13 127.3
C1—C2—C3 124.2 (3) C13—C14—S1 114.2 (5)
C1—C2—H2 117.9 C13—C14—H14 122.9
C3—C2—H2 117.9 S1—C14—H14 122.9
C8—C3—C4 118.7 (3) C13'—C12'—C11 118.0 (17)
C8—C3—C2 118.9 (3) C13'—C12'—H12' 121.0
C4—C3—C2 122.4 (3) C11—C12'—H12' 121.0
C5—C4—C3 120.8 (3) C14'—C13'—C12' 100.6 (19)
C5—C4—H4 119.6 C14'—C13'—H13' 129.7
C3—C4—H4 119.6 C12'—C13'—H13' 129.7
C4—C5—C6 120.4 (3) C13'—C14'—S1' 121.1 (17)
C4—C5—H5 119.8 C13'—C14'—H14B 119.4
C6—C5—H5 119.8 S1'—C14'—H14B 119.4
C7—C6—C5 120.6 (3) C20—C15—C16 119.1 (3)
C7—C6—H6 119.7 C20—C15—C1 118.8 (3)
C5—C6—H6 119.7 C16—C15—C1 122.0 (3)
C6—C7—C8 119.7 (3) C15—C16—C17 119.6 (3)
C6—C7—H7 120.2 C15—C16—H16 120.2
C8—C7—H7 120.2 C17—C16—H16 120.2
C3—C8—C7 119.9 (3) C18—C17—C16 120.9 (3)
C3—C8—C9 117.2 (2) C18—C17—H17 119.6
C7—C8—C9 122.8 (3) C16—C17—H17 119.6
N2—C9—N1 110.8 (3) C17—C18—C19 119.5 (3)
N2—C9—C8 127.9 (2) C17—C18—H18 120.2
N1—C9—C8 121.2 (3) C19—C18—H18 120.2
N3—C10—N1 109.2 (2) C18—C19—C20 120.0 (3)
N3—C10—C11 122.3 (2) C18—C19—H19 120.0
N1—C10—C11 128.5 (2) C20—C19—H19 120.0
C12—C11—C12' 99.4 (9) C19—C20—C15 120.9 (3)
C12—C11—C10 130.1 (3) C19—C20—H20 119.6
C12'—C11—C10 128.3 (9) C15—C20—H20 119.6
C12'—C11—S1' 111.4 (9)
C9—N2—N3—C10 −0.4 (3) N1—C10—C11—C12' 69.1 (13)
C9—N1—C1—C2 5.9 (4) N3—C10—C11—S1' 53.0 (4)
C10—N1—C1—C2 −176.4 (3) N1—C10—C11—S1' −129.4 (4)
C9—N1—C1—C15 −172.2 (2) N3—C10—C11—S1 −120.4 (3)
C10—N1—C1—C15 5.5 (5) N1—C10—C11—S1 57.2 (4)
N1—C1—C2—C3 −1.5 (5) C14'—S1'—C11—C12 −2(3)
C15—C1—C2—C3 176.5 (3) C14'—S1'—C11—C12' −10.5 (17)
C1—C2—C3—C8 −2.8 (5) C14'—S1'—C11—C10 −175.0 (13)
C1—C2—C3—C4 177.7 (4) C14'—S1'—C11—S1 −1.1 (13)
C8—C3—C4—C5 0.0 (5) C14—S1—C11—C12 1.2 (5)
C2—C3—C4—C5 179.6 (3) C14—S1—C11—C12' 58 (5)
C3—C4—C5—C6 0.5 (6) C14—S1—C11—C10 174.5 (3)
C4—C5—C6—C7 −0.3 (6) C14—S1—C11—S1' 1.0 (4)
C5—C6—C7—C8 −0.3 (5) C12'—C11—C12—C13 −12.8 (12)
C4—C3—C8—C7 −0.6 (5) C10—C11—C12—C13 −176.7 (7)
C2—C3—C8—C7 179.8 (3) S1'—C11—C12—C13 175 (3)
C4—C3—C8—C9 −177.6 (3) S1—C11—C12—C13 −4.0 (9)
C2—C3—C8—C9 2.8 (4) C11—C12—C13—C14 4.9 (11)
C6—C7—C8—C3 0.8 (5) C12—C13—C14—S1 −3.3 (8)
C6—C7—C8—C9 177.6 (3) C11—S1—C14—C13 1.3 (5)
N3—N2—C9—N1 1.2 (3) C12—C11—C12'—C13' 21 (2)
N3—N2—C9—C8 −175.8 (3) C10—C11—C12'—C13' −174.8 (14)
C10—N1—C9—N2 −1.4 (3) S1'—C11—C12'—C13' 23 (2)
C1—N1—C9—N2 176.9 (2) S1—C11—C12'—C13' −104 (6)
C10—N1—C9—C8 175.8 (3) C11—C12'—C13'—C14' −22 (3)
C1—N1—C9—C8 −5.9 (4) C12'—C13'—C14'—S1' 13 (3)
C3—C8—C9—N2 178.0 (3) C11—S1'—C14'—C13' −2(3)
C7—C8—C9—N2 1.2 (5) C2—C1—C15—C20 52.5 (4)
C3—C8—C9—N1 1.3 (4) N1—C1—C15—C20 −129.5 (3)
C7—C8—C9—N1 −175.5 (3) C2—C1—C15—C16 −124.6 (4)
N2—N3—C10—N1 −0.5 (3) N1—C1—C15—C16 53.4 (4)
N2—N3—C10—C11 177.5 (3) C20—C15—C16—C17 1.4 (4)
C9—N1—C10—N3 1.2 (3) C1—C15—C16—C17 178.5 (3)
C1—N1—C10—N3 −176.9 (3) C15—C16—C17—C18 −0.1 (4)
C9—N1—C10—C11 −176.6 (3) C16—C17—C18—C19 −1.2 (5)
C1—N1—C10—C11 5.3 (5) C17—C18—C19—C20 1.1 (5)
N3—C10—C11—C12 51.1 (6) C18—C19—C20—C15 0.2 (5)
N1—C10—C11—C12 −131.3 (5) C16—C15—C20—C19 −1.5 (4)
N3—C10—C11—C12' −108.5 (13) C1—C15—C20—C19 −178.7 (3)
Open in a new tab

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2984).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  2. Bruker (2004). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  4. Nadkarni, B. A., Kamat, V. R. & Khadse, B. G. (2001). Arzneim. Forsch.51, 569–573. [DOI] [PubMed]
  5. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Westrip, S. P. (2010). publCIF In preparation.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003181/lh2984sup1.cif

e-66-0o488-sup1.cif (20.3KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003181/lh2984Isup2.hkl

e-66-0o488-Isup2.hkl (180KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES