Acta Cryst. (2010). E66, o488 [ doi:10.1107/S1600536810003181 ]
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).
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.
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.
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).
![[Figure 1]](./lh2984fig1thm.gif)
| Fig. 1. 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. |
| 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 |
| 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 |
| 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) |
| C20H13N3S | V = 1613.7 (2) Å3 |
| Mr = 327.39 | Z = 4 |
| Orthorhombic, P21212 | Mo Kα radiation |
| a = 19.7715 (17) Å | µ = 0.21 mm−1 |
| b = 8.7735 (7) Å | T = 293 K |
| c = 9.3027 (8) Å | 0.32 × 0.30 × 0.24 mm |
| Bruker SMART area-detector diffractometer | 3670 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2414 reflections with I > 2σ(I) |
| Tmin = 0.937, Tmax = 0.952 | Rint = 0.045 |
| 10809 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
| wR(F2) = 0.128 | Δρmax = 0.20 e Å−3 |
| S = 1.03 | Δρmin = −0.21 e Å−3 |
| 3670 reflections | Absolute structure: Flack (1983), 1631 Friedel pairs |
| 230 parameters | Flack parameter: 0.05 (13) |
| 45 restraints |
| 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* |
| 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) |
| 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) |
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.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2004). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Nadkarni, B. A., Kamat, V. R. & Khadse, B. G. (2001). Arzneim. Forsch. 51, 569–573.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2010). publCIF. In preparation.
The molecular structure of the title compound is shown in Fig. 1.