(E)-N-(1-Benzothio-phen-3-yl-methyl-idene)-2,6-dimethyl-aniline.

In the title compound, C(17)H(15)NS, the benzothio-phene residue and the substituted benzene ring are oriented at a dihedral angle of 61.99 (7)°. An inter-molecular C-H⋯π inter-action contributes to the stability of the crystal structure.

Related literature

Fan class="Chemical">on>r the biological properties of Schiff bases, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶). For industrial applications of Schiff bases, see: Taggi et al. (2002 ▶). For chemical properties of Schiff bases, see: Aydoğan et al. (2001 ▶); Tanak et al. (2010 ▶); Ingold (1969 ▶). For related structures, see: Ağar et al. (2010 ▶); Ceylan et al. (2011 ▶); Dege, Şekerci et al. (2006 ▶); Demirtaş et al. (2009 ▶); Dege, Içbudak & Adıyaman (2006 ▶, 2007 ▶); Genç et al. (2004 ▶); İnaç et al. (2012 ▶); Tecer et al. (2010 ▶). For the structural properties benzothiophene derivatives, see: Alarcon et al. (1999 ▶); Cohen et al. (1964 ▶); Hadjoudis et al. (1987 ▶); Inamoto et al. (2008 ▶); Köysal et al. (2007 ▶); Karabıyık et al. (2008 ▶); Kobayashi et al. (2009 ▶); Mlochowski & Potaczek (2009 ▶); Novopoltseva (1995 ▶); Tanak et al. (2010 ▶); Xu et al. (1994 ▶); Zhang et al. (2001 ▶).

Experimental

Crystal data

C17H15NS

M = 265.36

Monoclinic,

a = 8.0446 (10) Å

b = 8.8031 (9) Å

c = 10.2809 (10) Å

β = 98.989 (11)°

V = 719.12 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.17 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.965, T max = 0.975

2788 measured reflections

2024 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 1.05

2024 reflections

174 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 497 Friedel pairs

Flack parameter: 0.10 (11)

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: OLEX2, WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004151/bt5806sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004151/bt5806Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004151/bt5806Isup3.cml

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

C17H15NS	F(000) = 280
Mr = 265.36	Dx = 1.225 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1387 reflections
a = 8.0446 (10) Å	θ = 3.5–27.3°
b = 8.8031 (9) Å	µ = 0.21 mm−1
c = 10.2809 (10) Å	T = 296 K
β = 98.989 (11)°	Prism, brown
V = 719.12 (14) Å3	0.17 × 0.15 × 0.12 mm
Z = 2

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer	2024 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1722 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 16.0454 pixels mm-1	θmax = 27.4°, θmin = 3.5°
ω scans	h = −10→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −5→11
Tmin = 0.965, Tmax = 0.975	l = −10→13
2788 measured reflections

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.1075P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2024 reflections	Δρmax = 0.15 e Å−3
174 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.10 (11)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
S1	0.82893 (13)	0.27137 (12)	0.24201 (7)	0.0801 (3)
N1	0.9883 (3)	0.2484 (3)	0.7306 (2)	0.0511 (6)
C10	1.0962 (3)	0.1995 (3)	0.8467 (2)	0.0491 (7)
C7	0.9176 (4)	0.2495 (4)	0.4948 (2)	0.0565 (7)
C6	0.7680 (3)	0.3424 (3)	0.4760 (2)	0.0453 (6)
C11	1.0246 (4)	0.1127 (4)	0.9370 (3)	0.0567 (8)
C5	0.6838 (4)	0.4137 (4)	0.5683 (3)	0.0560 (8)
H5	0.7222	0.4028	0.6579	0.067*
C2	0.5615 (4)	0.4471 (4)	0.2995 (3)	0.0659 (9)
H2	0.5210	0.4585	0.2103	0.079*
C13	1.2877 (5)	0.1134 (5)	1.0815 (3)	0.0766 (11)
H13	1.3528	0.0846	1.1605	0.092*
C15	1.2650 (4)	0.2449 (4)	0.8730 (3)	0.0590 (8)
C1	0.7043 (4)	0.3622 (3)	0.3416 (3)	0.0551 (8)
C9	1.0162 (4)	0.2036 (4)	0.6197 (3)	0.0575 (8)
H9	1.1054	0.1370	0.6173	0.069*
C14	1.3571 (4)	0.2000 (5)	0.9925 (4)	0.0784 (12)
H14	1.4692	0.2294	1.0129	0.094*
C3	0.4813 (5)	0.5139 (5)	0.3930 (3)	0.0772 (11)
H3	0.3835	0.5696	0.3671	0.093*
C12	1.1233 (4)	0.0697 (4)	1.0539 (3)	0.0695 (9)
H12	1.0771	0.0105	1.1141	0.083*
C4	0.5443 (4)	0.4995 (5)	0.5254 (3)	0.0698 (10)
H4	0.4904	0.5494	0.5869	0.084*
C8	0.9607 (5)	0.2058 (4)	0.3779 (3)	0.0772 (11)
H8	1.0539	0.1452	0.3720	0.093*
C17	0.8439 (4)	0.0649 (6)	0.9089 (4)	0.0854 (12)
H17A	0.7741	0.1528	0.8880	0.128*
H17B	0.8135	0.0155	0.9850	0.128*
H17C	0.8282	−0.0040	0.8357	0.128*
C16	1.3420 (5)	0.3460 (6)	0.7799 (4)	0.0923 (12)
H16A	1.3583	0.2888	0.7033	0.138*
H16C	1.4485	0.3834	0.8231	0.138*
H16B	1.2681	0.4300	0.7538	0.138*

	U11	U22	U33	U12	U13	U23
S1	0.1139 (8)	0.0853 (7)	0.0394 (4)	0.0236 (6)	0.0066 (4)	−0.0016 (5)
N1	0.0541 (12)	0.0557 (15)	0.0416 (11)	0.0048 (12)	0.0016 (10)	0.0060 (12)
C10	0.0502 (14)	0.0525 (17)	0.0424 (14)	0.0067 (14)	0.0003 (12)	−0.0035 (13)
C7	0.0698 (18)	0.0563 (19)	0.0427 (13)	0.0091 (16)	0.0063 (13)	0.0045 (15)
C6	0.0565 (15)	0.0399 (15)	0.0375 (13)	−0.0026 (13)	0.0012 (11)	0.0045 (12)
C11	0.0616 (17)	0.065 (2)	0.0417 (15)	0.0004 (16)	0.0021 (13)	0.0005 (15)
C5	0.0612 (18)	0.062 (2)	0.0426 (15)	0.0031 (16)	0.0024 (13)	0.0041 (15)
C2	0.078 (2)	0.065 (2)	0.0483 (16)	0.0040 (18)	−0.0110 (16)	0.0069 (16)
C13	0.073 (2)	0.099 (3)	0.0517 (18)	0.025 (2)	−0.0101 (17)	0.003 (2)
C15	0.0512 (16)	0.064 (2)	0.0607 (16)	−0.0009 (16)	0.0049 (14)	−0.0074 (18)
C1	0.075 (2)	0.0468 (17)	0.0405 (15)	−0.0068 (16)	0.0007 (14)	0.0026 (13)
C9	0.0655 (18)	0.058 (2)	0.0466 (15)	0.0141 (16)	0.0024 (14)	0.0058 (14)
C14	0.0481 (16)	0.100 (3)	0.082 (2)	0.0119 (19)	−0.0083 (17)	−0.025 (2)
C3	0.075 (2)	0.085 (3)	0.066 (2)	0.020 (2)	−0.0052 (18)	0.008 (2)
C12	0.083 (2)	0.074 (2)	0.0495 (18)	0.015 (2)	0.0025 (17)	0.0097 (18)
C4	0.069 (2)	0.081 (3)	0.058 (2)	0.0190 (19)	0.0062 (17)	0.0024 (18)
C8	0.098 (3)	0.081 (3)	0.0517 (18)	0.028 (2)	0.0096 (17)	0.0013 (18)
C17	0.072 (2)	0.114 (3)	0.068 (2)	−0.025 (2)	0.0046 (19)	0.016 (2)
C16	0.077 (2)	0.099 (3)	0.102 (3)	−0.019 (2)	0.020 (2)	−0.005 (2)

S1—C8	1.717 (3)	C13—C12	1.363 (5)
S1—C1	1.736 (3)	C13—C14	1.375 (5)
N1—C9	1.260 (3)	C13—H13	0.9300
N1—C10	1.428 (3)	C15—C14	1.390 (4)
C10—C11	1.395 (4)	C15—C16	1.509 (5)
C10—C15	1.400 (4)	C9—H9	0.9300
C7—C8	1.357 (4)	C14—H14	0.9300
C7—C6	1.442 (4)	C3—C4	1.382 (5)
C7—C9	1.456 (4)	C3—H3	0.9300
C6—C5	1.398 (4)	C12—H12	0.9300
C6—C1	1.407 (3)	C4—H4	0.9300
C11—C12	1.386 (4)	C8—H8	0.9300
C11—C17	1.497 (4)	C17—H17A	0.9600
C5—C4	1.367 (4)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C2—C3	1.371 (5)	C16—H16A	0.9600
C2—C1	1.382 (4)	C16—H16C	0.9600
C2—H2	0.9300	C16—H16B	0.9600
C8—S1—C1	90.84 (15)	N1—C9—H9	117.9
C9—N1—C10	119.5 (2)	C7—C9—H9	117.9
C11—C10—C15	121.1 (2)	C13—C14—C15	122.0 (3)
C11—C10—N1	117.4 (2)	C13—C14—H14	119.0
C15—C10—N1	121.3 (3)	C15—C14—H14	119.0
C8—C7—C6	111.4 (2)	C2—C3—C4	120.7 (3)
C8—C7—C9	121.5 (3)	C2—C3—H3	119.6
C6—C7—C9	127.1 (2)	C4—C3—H3	119.6
C5—C6—C1	118.0 (3)	C13—C12—C11	120.6 (3)
C5—C6—C7	130.2 (2)	C13—C12—H12	119.7
C1—C6—C7	111.7 (2)	C11—C12—H12	119.7
C12—C11—C10	119.1 (3)	C5—C4—C3	121.6 (3)
C12—C11—C17	119.9 (3)	C5—C4—H4	119.2
C10—C11—C17	121.0 (3)	C3—C4—H4	119.2
C4—C5—C6	119.3 (3)	C7—C8—S1	114.5 (3)
C4—C5—H5	120.3	C7—C8—H8	122.7
C6—C5—H5	120.3	S1—C8—H8	122.7
C3—C2—C1	118.2 (3)	C11—C17—H17A	109.5
C3—C2—H2	120.9	C11—C17—H17B	109.5
C1—C2—H2	120.9	H17A—C17—H17B	109.5
C12—C13—C14	120.0 (3)	C11—C17—H17C	109.5
C12—C13—H13	120.0	H17A—C17—H17C	109.5
C14—C13—H13	120.0	H17B—C17—H17C	109.5
C14—C15—C10	117.2 (3)	C15—C16—H16A	109.5
C14—C15—C16	120.9 (3)	C15—C16—H16C	109.5
C10—C15—C16	121.8 (3)	H16A—C16—H16C	109.5
C2—C1—C6	122.1 (3)	C15—C16—H16B	109.5
C2—C1—S1	126.4 (2)	H16A—C16—H16B	109.5
C6—C1—S1	111.5 (2)	H16C—C16—H16B	109.5
N1—C9—C7	124.2 (3)
C9—N1—C10—C11	−117.4 (3)	C5—C6—C1—S1	177.9 (2)
C9—N1—C10—C15	66.6 (4)	C7—C6—C1—S1	−1.2 (3)
C8—C7—C6—C5	−178.2 (3)	C8—S1—C1—C2	179.8 (3)
C9—C7—C6—C5	1.9 (6)	C8—S1—C1—C6	1.0 (2)
C8—C7—C6—C1	0.7 (4)	C10—N1—C9—C7	−178.1 (3)
C9—C7—C6—C1	−179.2 (3)	C8—C7—C9—N1	175.4 (4)
C15—C10—C11—C12	−0.7 (5)	C6—C7—C9—N1	−4.7 (5)
N1—C10—C11—C12	−176.8 (3)	C12—C13—C14—C15	−0.4 (6)
C15—C10—C11—C17	179.7 (3)	C10—C15—C14—C13	0.6 (5)
N1—C10—C11—C17	3.6 (5)	C16—C15—C14—C13	177.2 (4)
C1—C6—C5—C4	−0.2 (5)	C1—C2—C3—C4	1.5 (6)
C7—C6—C5—C4	178.7 (3)	C14—C13—C12—C11	−0.5 (6)
C11—C10—C15—C14	−0.1 (5)	C10—C11—C12—C13	1.0 (5)
N1—C10—C15—C14	175.8 (3)	C17—C11—C12—C13	−179.4 (4)
C11—C10—C15—C16	−176.6 (3)	C6—C5—C4—C3	2.0 (6)
N1—C10—C15—C16	−0.7 (5)	C2—C3—C4—C5	−2.7 (6)
C3—C2—C1—C6	0.3 (5)	C6—C7—C8—S1	0.1 (4)
C3—C2—C1—S1	−178.4 (3)	C9—C7—C8—S1	180.0 (3)
C5—C6—C1—C2	−1.0 (4)	C1—S1—C8—C7	−0.7 (3)
C7—C6—C1—C2	180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg2i	0.93	2.95	3.872 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg2i	0.93	2.95	3.872 (4)	171

Symmetry code: (i) .