2-Amino-4-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile.

In the title compound, C(10)H(12)N(2)S, the thio-phene ring is essentially planar (r.m.s. deviation = 0.0290 Å). The two C atoms of the cyclo-hexene ring (at positions 6 and 7) are disordered over two sets of sites in a 0.810 (5):0.190 (5) ratio. The cyclo-hexene rings in both the major and minor occupancy conformers adopt a half-chair conformation. In the crystal, there are two types of N-H⋯N inter-action. One of these results in centrosymmetric head-to-head dimers corresponding to an R(2) (2)(12) graph-set motif and the other forms a 20-membered macrocyclic ring involving six mol-ecules.

Related literature

For biological activities of benzothio­phenes, see: Shetty et al. (2009 ▶). For the crystal structure of a closely related compound, see: Ziaulla et al. (2011 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12N2S

M = 192.28

Monoclinic,

a = 9.6771 (2) Å

b = 7.6364 (2) Å

c = 13.8156 (3) Å

β = 100.221 (2)°

V = 1004.75 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 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 = 0.952, T max = 0.957

8861 measured reflections

2195 independent reflections

1812 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.118

S = 1.06

2195 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1998 ▶); 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 datablock(s) global, I. DOI: 10.1107/S160053681204010X/pv2585sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204010X/pv2585Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681204010X/pv2585Isup3.cml

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

C10H12N2S	F(000) = 408
Mr = 192.28	Dx = 1.271 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2195 reflections
a = 9.6771 (2) Å	θ = 2.1–27.0°
b = 7.6364 (2) Å	µ = 0.28 mm−1
c = 13.8156 (3) Å	T = 296 K
β = 100.221 (2)°	Block, yellow
V = 1004.75 (4) Å3	0.18 × 0.16 × 0.16 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	2195 independent reflections
Radiation source: fine-focus sealed tube	1812 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
Tmin = 0.952, Tmax = 0.957	k = −9→9
8861 measured reflections	l = −17→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1371P] where P = (Fo2 + 2Fc2)/3
2195 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.25 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	Occ. (<1)
S1	0.71234 (4)	0.00203 (5)	0.83213 (3)	0.05244 (18)
C3	0.65478 (15)	0.14987 (19)	0.98594 (10)	0.0421 (3)
C1	0.59583 (16)	0.2640 (2)	1.04856 (10)	0.0472 (4)
N2	0.54845 (17)	0.3532 (2)	1.10080 (11)	0.0653 (4)
C2	0.63578 (15)	0.17225 (19)	0.88557 (10)	0.0439 (3)
C9	0.76862 (16)	−0.0986 (2)	0.94522 (11)	0.0481 (4)
C8	0.73216 (16)	−0.00656 (18)	1.01974 (11)	0.0420 (3)
N1	0.57113 (16)	0.3034 (2)	0.82953 (10)	0.0650 (4)
H1A	0.5345	0.3890	0.8566	0.078*
H1B	0.5666	0.3014	0.7668	0.078*
C10	0.8661 (2)	0.0583 (3)	1.18824 (14)	0.0791 (6)
H10A	0.8837	0.0168	1.2549	0.119*
H10B	0.8258	0.1734	1.1861	0.119*
H10C	0.9528	0.0626	1.1637	0.119*
C4	0.76560 (17)	−0.0641 (2)	1.12553 (12)	0.0528 (4)
H4	0.6773	−0.0591	1.1509	0.063*	0.810 (5)
C5	0.8427 (2)	−0.2719 (2)	0.95380 (14)	0.0663 (5)
H5A	0.9131	−0.2740	0.9118	0.080*	0.810 (5)
H5B	0.7762	−0.3655	0.9336	0.080*	0.810 (5)
C7	0.8107 (4)	−0.2568 (4)	1.1298 (2)	0.0708 (8)	0.810 (5)
H7A	0.8542	−0.2857	1.1966	0.085*	0.810 (5)
H7B	0.7281	−0.3300	1.1123	0.085*	0.810 (5)
C6	0.9126 (4)	−0.2970 (4)	1.06146 (19)	0.0730 (8)	0.810 (5)
H6A	0.9452	−0.4168	1.0715	0.088*	0.810 (5)
H6B	0.9934	−0.2202	1.0766	0.088*	0.810 (5)
C4'	0.76560 (17)	−0.0641 (2)	1.12553 (12)	0.0528 (4)	0.00
H4A	0.6823	−0.0925	1.1538	0.063*	0.190 (5)
C5'	0.8427 (2)	−0.2719 (2)	0.95380 (14)	0.0663 (5)	0.00
H5C	0.9410	−0.2557	0.9498	0.080*	0.190 (5)
H5D	0.8009	−0.3485	0.9006	0.080*	0.190 (5)
C7'	0.8760 (17)	−0.2149 (18)	1.1356 (10)	0.0708 (8)	0.190 (5)
H7C	0.8836	−0.2697	1.1996	0.085*	0.190 (5)
H7D	0.9673	−0.1679	1.1297	0.085*	0.190 (5)
C6'	0.8294 (17)	−0.3534 (17)	1.0531 (9)	0.0730 (8)	0.190 (5)
H6C	0.8883	−0.4567	1.0650	0.088*	0.190 (5)
H6D	0.7329	−0.3882	1.0528	0.088*	0.190 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0652 (3)	0.0563 (3)	0.0354 (2)	0.01326 (18)	0.00757 (18)	−0.00553 (16)
C3	0.0464 (7)	0.0441 (8)	0.0358 (7)	−0.0006 (6)	0.0074 (5)	−0.0036 (6)
C1	0.0574 (9)	0.0472 (8)	0.0362 (7)	0.0016 (7)	0.0063 (6)	−0.0003 (6)
N2	0.0859 (11)	0.0645 (9)	0.0477 (8)	0.0141 (8)	0.0176 (7)	−0.0073 (7)
C2	0.0486 (8)	0.0458 (8)	0.0369 (7)	0.0041 (6)	0.0062 (6)	−0.0016 (6)
C9	0.0532 (8)	0.0470 (9)	0.0435 (8)	0.0064 (7)	0.0073 (6)	0.0019 (6)
C8	0.0429 (7)	0.0449 (8)	0.0373 (8)	−0.0026 (6)	0.0044 (6)	0.0023 (6)
N1	0.0891 (11)	0.0662 (9)	0.0391 (7)	0.0320 (8)	0.0095 (7)	0.0061 (6)
C10	0.0743 (13)	0.1082 (17)	0.0479 (11)	−0.0107 (12)	−0.0082 (9)	0.0044 (11)
C4	0.0556 (9)	0.0618 (10)	0.0413 (8)	−0.0008 (8)	0.0095 (7)	0.0107 (8)
C5	0.0798 (12)	0.0545 (10)	0.0669 (12)	0.0193 (9)	0.0196 (9)	0.0058 (9)
C7	0.083 (2)	0.0661 (16)	0.0646 (14)	0.0052 (14)	0.0166 (15)	0.0268 (12)
C6	0.0775 (19)	0.0668 (16)	0.0730 (15)	0.0256 (14)	0.0090 (14)	0.0181 (12)
C4'	0.0556 (9)	0.0618 (10)	0.0413 (8)	−0.0008 (8)	0.0095 (7)	0.0107 (8)
C5'	0.0798 (12)	0.0545 (10)	0.0669 (12)	0.0193 (9)	0.0196 (9)	0.0058 (9)
C7'	0.083 (2)	0.0661 (16)	0.0646 (14)	0.0052 (14)	0.0166 (15)	0.0268 (12)
C6'	0.0775 (19)	0.0668 (16)	0.0730 (15)	0.0256 (14)	0.0090 (14)	0.0181 (12)

S1—C2	1.7256 (14)	C4—C7	1.533 (3)
S1—C9	1.7397 (16)	C4—H4	0.9800
C3—C2	1.3768 (19)	C5—C6	1.533 (3)
C3—C1	1.417 (2)	C5—H5A	0.9700
C3—C8	1.443 (2)	C5—H5B	0.9700
C1—N2	1.146 (2)	C7—C6	1.513 (5)
C2—N1	1.3499 (19)	C7—H7A	0.9700
C9—C8	1.345 (2)	C7—H7B	0.9700
C9—C5	1.500 (2)	C6—H6A	0.9700
C8—C4	1.505 (2)	C6—H6B	0.9700
N1—H1A	0.8600	C7'—C6'	1.56 (2)
N1—H1B	0.8600	C7'—H7C	0.9700
C10—C4	1.507 (3)	C7'—H7D	0.9700
C10—H10A	0.9600	C6'—H6C	0.9700
C10—H10B	0.9600	C6'—H6D	0.9700
C10—H10C	0.9600
C2—S1—C9	92.20 (7)	C10—C4—H4	106.5
C2—C3—C1	122.84 (14)	C7—C4—H4	106.5
C2—C3—C8	113.43 (13)	C9—C5—C6	108.02 (16)
C1—C3—C8	123.61 (13)	C9—C5—H5A	110.1
N2—C1—C3	178.40 (17)	C6—C5—H5A	110.1
N1—C2—C3	129.43 (14)	C9—C5—H5B	110.1
N1—C2—S1	120.27 (11)	C6—C5—H5B	110.1
C3—C2—S1	110.29 (11)	H5A—C5—H5B	108.4
C8—C9—C5	125.99 (15)	C6—C7—C4	112.5 (2)
C8—C9—S1	111.95 (12)	C6—C7—H7A	109.1
C5—C9—S1	122.00 (12)	C4—C7—H7A	109.1
C9—C8—C3	112.13 (14)	C6—C7—H7B	109.1
C9—C8—C4	123.39 (14)	C4—C7—H7B	109.1
C3—C8—C4	124.46 (14)	H7A—C7—H7B	107.8
C2—N1—H1A	120.0	C7—C6—C5	110.9 (3)
C2—N1—H1B	120.0	C7—C6—H6A	109.5
H1A—N1—H1B	120.0	C5—C6—H6A	109.5
C4—C10—H10A	109.5	C7—C6—H6B	109.5
C4—C10—H10B	109.5	C5—C6—H6B	109.5
H10A—C10—H10B	109.5	H6A—C6—H6B	108.1
C4—C10—H10C	109.5	C6'—C7'—H7C	109.8
H10A—C10—H10C	109.5	C6'—C7'—H7D	109.8
H10B—C10—H10C	109.5	H7C—C7'—H7D	108.3
C8—C4—C10	112.49 (15)	C7'—C6'—H6C	110.0
C8—C4—C7	109.16 (16)	C7'—C6'—H6D	110.0
C10—C4—C7	115.0 (2)	H6C—C6'—H6D	108.4
C8—C4—H4	106.5
C2—C3—C1—N2	158 (6)	C2—C3—C8—C9	−0.47 (19)
C8—C3—C1—N2	−17 (6)	C1—C3—C8—C9	175.63 (14)
C1—C3—C2—N1	5.0 (3)	C2—C3—C8—C4	−178.94 (14)
C8—C3—C2—N1	−178.86 (16)	C1—C3—C8—C4	−2.8 (2)
C1—C3—C2—S1	−176.09 (12)	C9—C8—C4—C10	114.82 (19)
C8—C3—C2—S1	0.05 (16)	C3—C8—C4—C10	−66.9 (2)
C9—S1—C2—N1	179.29 (14)	C9—C8—C4—C7	−14.1 (3)
C9—S1—C2—C3	0.28 (12)	C3—C8—C4—C7	164.16 (19)
C2—S1—C9—C8	−0.56 (13)	C8—C9—C5—C6	−18.6 (3)
C2—S1—C9—C5	176.80 (15)	S1—C9—C5—C6	164.40 (18)
C5—C9—C8—C3	−176.56 (16)	C8—C4—C7—C6	44.6 (3)
S1—C9—C8—C3	0.67 (17)	C10—C4—C7—C6	−82.9 (3)
C5—C9—C8—C4	1.9 (3)	C4—C7—C6—C5	−64.8 (4)
S1—C9—C8—C4	179.16 (12)	C9—C5—C6—C7	47.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.24	3.088 (2)	167
N1—H1B···N2ii	0.86	2.56	3.349 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.24	3.088 (2)	167
N1—H1B⋯N2ii	0.86	2.56	3.349 (2)	153

Symmetry codes: (i) ; (ii) .