5-Phenyl-3-(2-thien-yl)-1,2,4-triazolo[3,4-a]isoquinoline.

In the title mol-ecule, C(20)H(13)N(3)S, 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 thio-phene ring. The phenyl ring is twisted by 52.0 (1)° with respect to the mean plane of the triazoloisoquinoline ring system. The thio-phene 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 ▶).

Experimental

Crystal data

C20H13N3S

M = 327.39

Orthorhombic,

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 ▶).

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

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

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

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)

	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)