2-Phenyl-8,9,10,11-tetra-hydro-1-benzo-thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine.

In the title compound, C(17)H(14)N(4)S, the benzothieno moiety is fused at one end of the pyramidine ring while the triazole ring with a phenyl substituent is fused at the other side. The triazole ring is almost planar [maximum deviation = 0.0028 (3) Å] while the cyclo-hexane ring adopts a half-chair conformation. In the crystal, pairs of inter-molecular C-H⋯N hydrogen bonds form centrosymmetric head-to-head dimers, corresponding to an R(2) (2)(8) graph-set motif. Further C-H⋯N inter-actions generate a zigzag chain of mol-ecules along the c axis. The supra-molecular assembly is consolidated by π-π stacking inter-actions [centroid-centroid distance = 3.445 (4) Å].

Related literature

For the biological activity of thio­phenes, benzothio­phenes, pyrimidines and triazolopyrimidines, see: Shishoo & Jain (1992 ▶); Bradbury & Rivett (1991 ▶); Elslager et al. (1981 ▶); Yunosov et al. (1966 ▶); Blain et al. (1982 ▶). For related structures, see: Akkurt et al. (2008 ▶); Buzykin et al. (2008 ▶); Harrison et al. (2006 ▶); Lipson et al. (2006 ▶); Belcher & Squattrito (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. 1995 ▶). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C17H14N4S

M = 306.38

Monoclinic,

a = 8.6239 (16) Å

b = 20.512 (4) Å

c = 8.5952 (16) Å

β = 111.975 (3)°

V = 1410.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.960, T max = 0.964

8272 measured reflections

3042 independent reflections

2345 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.202

S = 1.25

3042 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.66 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997) ▶ and CAMERON (Watkin et al., 1996) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007331/pb2056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007331/pb2056Isup2.hkl

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

C17H14N4S	F(000) = 640
Mr = 306.38	Dx = 1.443 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3042 reflections
a = 8.6239 (16) Å	θ = 2.6–27.0°
b = 20.512 (4) Å	µ = 0.23 mm−1
c = 8.5952 (16) Å	T = 296 K
β = 111.975 (3)°	Block, white
V = 1410.0 (5) Å3	0.18 × 0.16 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	3042 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω scans	θmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→11
Tmin = 0.960, Tmax = 0.964	k = −26→19
8272 measured reflections	l = −10→10

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.25	w = 1/[σ2(Fo2) + (0.1054P)2] where P = (Fo2 + 2Fc2)/3
3042 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	−0.1145 (3)	0.57323 (12)	0.5033 (3)	0.0166 (6)
C2	−0.2370 (3)	0.52330 (12)	0.4477 (3)	0.0160 (6)
C3	−0.4107 (3)	0.44589 (13)	0.3912 (3)	0.0163 (6)
C4	−0.5006 (3)	0.38839 (13)	0.4128 (3)	0.0177 (6)
C5	−0.3157 (3)	0.56670 (13)	0.1641 (4)	0.0205 (6)
H5	−0.3857	0.5635	0.0517	0.025*
C6	−0.1062 (3)	0.61456 (13)	0.3786 (4)	0.0189 (6)
C7	0.0023 (3)	0.58943 (13)	0.6675 (3)	0.0174 (6)
C8	0.0944 (3)	0.64270 (13)	0.6629 (3)	0.0185 (6)
C9	0.2214 (4)	0.67497 (14)	0.8139 (4)	0.0228 (6)
H9A	0.2104	0.7220	0.8025	0.027*
H9B	0.3332	0.6631	0.8226	0.027*
C10	0.1936 (4)	0.65306 (15)	0.9725 (4)	0.0297 (7)
H10A	0.2879	0.6667	1.0710	0.036*
H10B	0.0940	0.6739	0.9760	0.036*
C11	0.1742 (4)	0.57928 (15)	0.9757 (4)	0.0292 (7)
H11A	0.1642	0.5667	1.0803	0.035*
H11B	0.2735	0.5586	0.9710	0.035*
C12	0.0201 (4)	0.55527 (13)	0.8282 (3)	0.0197 (6)
H12A	0.0296	0.5087	0.8144	0.024*
H12B	−0.0793	0.5629	0.8529	0.024*
C13	−0.6266 (3)	0.35972 (13)	0.2766 (4)	0.0187 (6)
H13	−0.6562	0.3776	0.1699	0.022*
C14	−0.7074 (4)	0.30477 (14)	0.3003 (4)	0.0216 (6)
H14	−0.7920	0.2862	0.2091	0.026*
C15	−0.6648 (4)	0.27684 (14)	0.4573 (4)	0.0213 (6)
H15	−0.7186	0.2393	0.4715	0.026*
C16	−0.5407 (4)	0.30559 (15)	0.5931 (4)	0.0232 (7)
H16	−0.5118	0.2875	0.6994	0.028*
C17	−0.4598 (3)	0.36091 (13)	0.5716 (4)	0.0211 (6)
H17	−0.3773	0.3800	0.6638	0.025*
N1	−0.3331 (3)	0.52294 (11)	0.2782 (3)	0.0170 (5)
N2	−0.4455 (3)	0.47305 (11)	0.2407 (3)	0.0190 (5)
N3	−0.2852 (3)	0.47484 (10)	0.5218 (3)	0.0173 (5)
N4	−0.2022 (3)	0.61279 (11)	0.2114 (3)	0.0202 (5)
S1	0.04561 (9)	0.67369 (3)	0.46182 (9)	0.0205 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0188 (14)	0.0123 (13)	0.0200 (14)	0.0057 (10)	0.0089 (11)	0.0046 (10)
C2	0.0157 (14)	0.0168 (13)	0.0145 (13)	0.0021 (10)	0.0044 (11)	−0.0027 (10)
C3	0.0148 (13)	0.0135 (13)	0.0187 (14)	0.0013 (10)	0.0039 (11)	−0.0001 (10)
C4	0.0193 (14)	0.0158 (13)	0.0182 (14)	0.0036 (11)	0.0072 (11)	0.0012 (11)
C5	0.0211 (15)	0.0189 (14)	0.0198 (15)	−0.0025 (11)	0.0057 (12)	0.0000 (11)
C6	0.0203 (15)	0.0161 (13)	0.0201 (15)	0.0041 (11)	0.0075 (12)	0.0011 (11)
C7	0.0173 (14)	0.0171 (14)	0.0169 (14)	0.0017 (11)	0.0055 (11)	−0.0026 (11)
C8	0.0173 (14)	0.0144 (13)	0.0216 (15)	0.0029 (11)	0.0048 (12)	−0.0019 (11)
C9	0.0213 (15)	0.0206 (15)	0.0240 (16)	−0.0038 (11)	0.0058 (12)	−0.0015 (11)
C10	0.0335 (18)	0.0271 (16)	0.0208 (16)	−0.0066 (14)	0.0015 (14)	−0.0032 (13)
C11	0.0303 (18)	0.0312 (17)	0.0210 (16)	−0.0031 (14)	0.0037 (14)	0.0018 (13)
C12	0.0223 (15)	0.0164 (14)	0.0181 (14)	−0.0019 (11)	0.0049 (12)	−0.0027 (11)
C13	0.0188 (15)	0.0186 (14)	0.0174 (14)	−0.0007 (11)	0.0054 (11)	−0.0009 (11)
C14	0.0193 (15)	0.0258 (15)	0.0204 (15)	−0.0018 (12)	0.0081 (12)	−0.0041 (12)
C15	0.0245 (15)	0.0165 (14)	0.0254 (16)	0.0010 (11)	0.0123 (13)	0.0011 (11)
C16	0.0215 (16)	0.0263 (16)	0.0201 (15)	−0.0030 (12)	0.0059 (12)	0.0042 (12)
C17	0.0174 (15)	0.0238 (15)	0.0194 (15)	−0.0007 (12)	0.0039 (12)	0.0028 (12)
N1	0.0164 (12)	0.0163 (11)	0.0172 (12)	−0.0049 (9)	0.0047 (10)	−0.0015 (9)
N2	0.0189 (12)	0.0180 (12)	0.0182 (12)	−0.0019 (9)	0.0048 (10)	−0.0020 (9)
N3	0.0186 (12)	0.0141 (11)	0.0192 (12)	0.0012 (9)	0.0071 (10)	0.0012 (9)
N4	0.0206 (13)	0.0204 (12)	0.0178 (12)	0.0017 (10)	0.0050 (10)	0.0032 (9)
S1	0.0209 (4)	0.0173 (4)	0.0224 (4)	−0.0018 (3)	0.0071 (3)	0.0017 (3)

C1—C6	1.389 (4)	C9—H9A	0.9700
C1—C2	1.420 (4)	C9—H9B	0.9700
C1—C7	1.433 (4)	C10—C11	1.524 (4)
C2—N3	1.329 (3)	C10—H10A	0.9700
C2—N1	1.380 (3)	C10—H10B	0.9700
C3—N2	1.336 (4)	C11—C12	1.535 (4)
C3—N3	1.369 (3)	C11—H11A	0.9700
C3—C4	1.461 (4)	C11—H11B	0.9700
C4—C17	1.395 (4)	C12—H12A	0.9700
C4—C13	1.395 (4)	C12—H12B	0.9700
C5—N4	1.311 (4)	C13—C14	1.380 (4)
C5—N1	1.379 (3)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.383 (4)
C6—N4	1.365 (4)	C14—H14	0.9300
C6—S1	1.731 (3)	C15—C16	1.386 (4)
C7—C8	1.360 (4)	C15—H15	0.9300
C7—C12	1.504 (4)	C16—C17	1.380 (4)
C8—C9	1.503 (4)	C16—H16	0.9300
C8—S1	1.739 (3)	C17—H17	0.9300
C9—C10	1.537 (4)	N1—N2	1.363 (3)
C6—C1—C2	115.3 (3)	H10A—C10—H10B	108.0
C6—C1—C7	113.5 (2)	C10—C11—C12	111.8 (3)
C2—C1—C7	131.2 (2)	C10—C11—H11A	109.3
N3—C2—N1	109.3 (2)	C12—C11—H11A	109.3
N3—C2—C1	134.9 (3)	C10—C11—H11B	109.3
N1—C2—C1	115.8 (2)	C12—C11—H11B	109.3
N2—C3—N3	115.8 (2)	H11A—C11—H11B	107.9
N2—C3—C4	121.5 (2)	C7—C12—C11	111.6 (2)
N3—C3—C4	122.7 (2)	C7—C12—H12A	109.3
C17—C4—C13	118.9 (2)	C11—C12—H12A	109.3
C17—C4—C3	119.9 (3)	C7—C12—H12B	109.3
C13—C4—C3	121.2 (3)	C11—C12—H12B	109.3
N4—C5—N1	121.0 (3)	H12A—C12—H12B	108.0
N4—C5—H5	119.5	C14—C13—C4	119.9 (3)
N1—C5—H5	119.5	C14—C13—H13	120.1
N4—C6—C1	127.6 (3)	C4—C13—H13	120.1
N4—C6—S1	121.4 (2)	C15—C14—C13	121.2 (3)
C1—C6—S1	111.0 (2)	C15—C14—H14	119.4
C8—C7—C1	111.1 (2)	C13—C14—H14	119.4
C8—C7—C12	122.8 (2)	C14—C15—C16	119.0 (3)
C1—C7—C12	126.1 (2)	C14—C15—H15	120.5
C7—C8—C9	125.0 (3)	C16—C15—H15	120.5
C7—C8—S1	113.3 (2)	C17—C16—C15	120.5 (3)
C9—C8—S1	121.7 (2)	C17—C16—H16	119.8
C8—C9—C10	109.4 (2)	C15—C16—H16	119.8
C8—C9—H9A	109.8	C16—C17—C4	120.5 (3)
C10—C9—H9A	109.8	C16—C17—H17	119.7
C8—C9—H9B	109.8	C4—C17—H17	119.7
C10—C9—H9B	109.8	N2—N1—C5	125.3 (2)
H9A—C9—H9B	108.2	N2—N1—C2	110.3 (2)
C11—C10—C9	111.2 (3)	C5—N1—C2	124.5 (2)
C11—C10—H10A	109.4	C3—N2—N1	101.6 (2)
C9—C10—H10A	109.4	C2—N3—C3	103.0 (2)
C11—C10—H10B	109.4	C5—N4—C6	115.7 (2)
C9—C10—H10B	109.4	C6—S1—C8	91.09 (13)
C6—C1—C2—N3	179.6 (3)	C3—C4—C13—C14	178.9 (2)
C7—C1—C2—N3	−1.3 (5)	C4—C13—C14—C15	−0.6 (4)
C6—C1—C2—N1	−0.9 (3)	C13—C14—C15—C16	1.2 (4)
C7—C1—C2—N1	178.1 (3)	C14—C15—C16—C17	−0.6 (4)
N2—C3—C4—C17	179.3 (2)	C15—C16—C17—C4	−0.5 (4)
N3—C3—C4—C17	0.2 (4)	C13—C4—C17—C16	1.1 (4)
N2—C3—C4—C13	−0.1 (4)	C3—C4—C17—C16	−178.3 (3)
N3—C3—C4—C13	−179.3 (2)	N4—C5—N1—N2	−179.1 (2)
C2—C1—C6—N4	0.6 (4)	N4—C5—N1—C2	0.3 (4)
C7—C1—C6—N4	−178.7 (3)	N3—C2—N1—N2	−0.4 (3)
C2—C1—C6—S1	179.33 (19)	C1—C2—N1—N2	−180.0 (2)
C7—C1—C6—S1	0.1 (3)	N3—C2—N1—C5	−179.9 (2)
C6—C1—C7—C8	0.5 (3)	C1—C2—N1—C5	0.5 (4)
C2—C1—C7—C8	−178.5 (3)	N3—C3—N2—N1	0.3 (3)
C6—C1—C7—C12	178.1 (2)	C4—C3—N2—N1	−179.0 (2)
C2—C1—C7—C12	−1.0 (5)	C5—N1—N2—C3	179.5 (2)
C1—C7—C8—C9	176.4 (2)	C2—N1—N2—C3	0.1 (3)
C12—C7—C8—C9	−1.2 (4)	N1—C2—N3—C3	0.5 (3)
C1—C7—C8—S1	−1.0 (3)	C1—C2—N3—C3	180.0 (3)
C12—C7—C8—S1	−178.6 (2)	N2—C3—N3—C2	−0.5 (3)
C7—C8—C9—C10	−17.3 (4)	C4—C3—N3—C2	178.7 (2)
S1—C8—C9—C10	159.9 (2)	N1—C5—N4—C6	−0.7 (4)
C8—C9—C10—C11	47.7 (3)	C1—C6—N4—C5	0.3 (4)
C9—C10—C11—C12	−62.6 (4)	S1—C6—N4—C5	−178.4 (2)
C8—C7—C12—C11	−11.0 (4)	N4—C6—S1—C8	178.3 (2)
C1—C7—C12—C11	171.7 (3)	C1—C6—S1—C8	−0.5 (2)
C10—C11—C12—C7	42.0 (3)	C7—C8—S1—C6	0.9 (2)
C17—C4—C13—C14	−0.6 (4)	C9—C8—S1—C6	−176.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2i	0.93	2.50	3.413 (3)	166
C11—H11B···N2ii	0.97	2.82	3.653 (5)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2i	0.93	2.50	3.413 (3)	166
C11—H11B⋯N2ii	0.97	2.82	3.653 (5)	144

Symmetry codes: (i) ; (ii) .