(E)-N-(1-Benzothio­phen-3-yl­methyl­idene)-2,6-dimethyl­aniline

Kahveci Yağcı, N.; Dege, N.; Gümüş, S.; Ağar, E.; Soylu, M.S.

doi:10.1107/S1600536812004151

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o623-o624

doi:10.1107/S1600536812004151

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(E)-N-(1-Benzothiophen-3-ylmethylidene)-2,6-dimethylaniline

Nermin Kahveci Yağcı,^a Necmi Dege,^b ^* Sümeyye Gümüş,^c Erbil Ağar ^c and Mustafa Serkan Soylu ^d

^aKırıkkale University, Faculty of Arts and Sciences, Physics Department, 71450 Kırıkkale, Turkey, ^bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, ^cOndokuz Mayıs University, Arts and Sciences Faculty, Department of Chemistry, 55139 Samsun, Turkey, and ^dGiresun University, Faculty of Arts and Sciences, Department of Physics, 28100 Giresun, Turkey
^*Correspondence e-mail: necmisamsun@gmail.com

(Received 26 January 2012; accepted 31 January 2012; online 4 February 2012)

In the title compound, C₁₇H₁₅NS, the benzothiophene residue and the substituted benzene ring are oriented at a dihedral angle of 61.99 (7)°. An intermolecular C—H⋯π interaction contributes to the stability of the crystal structure.

Related literature

For 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_r = 265.36
Monoclinic, P 2₁
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 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) 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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.05
2024 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 497 Friedel pairs
Flack parameter: 0.10 (11)

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) $[-x, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004151/bt5806sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812004151/bt5806Isup3.cml

checkCIF report

Comment top

Benzothiophene derivatives are undoubtedly one of the most important classes of heterocycles, because some of molecules having the benzothiophene skeleton have been reported to axhibit wide variety of biological activities (Kobayashi et al., 2009). Therefore, we (İnaç et al. 2012) and others (İnamoto et al., 2008; Mlochowski & Potaczek, 2009) have recently reported efficient methods for the synthesis of benzothiophenes. However, there are only a few reports on the synthesis of 1-(benzo[b]thiophen-3-yl)-N-methylmethanamines, which may also be of potential biological importance.

Schiff bases, i.e., compounds having a double C=N bond, are used as starting materials in the synthesis of important drugs, such as antibiotics and antiallergic, antiphlogistic, and antitumor substances (Barton & Ollis, 1979; Layer, 1963; Ingold 1969). On the industrial scale, they have a wide range of applications, such as dyes and pigments (Taggi et al., 2002). They are also used as components of rubber compounds (Novopoltseva, 1995). Schiff base compounds display interesting photochromic and thermochromic features in the solid state and can be classified in terms of these properties (Cohen et al., 1964). Photo- and thermochromism arise via H-atom transfer from the hydroxy O atom to the imine N atom (Hadjoudis et al., 1987;Xu et al., 1994). Such proton-exchanging materials can be utilized for the design of various molecular electronic devices (Alarcon et al., 1999). In general, Schiff bases display two possible tautomeric forms, the phenol-imine (OH) and the keto-amine (NH) forms. Depending on the tautomers, two types of intramolecular hydrogen bonds are observed in Schiff bases: O—H···N in phenol-imine (Köysal et al., 2007) and N—H···O in keto-amine tautomers. By means of increasing development of computational chemistry in the past decade, the research of theoretical modeling of drug design, functional material design, etc., has become more mature than ever. Many important chemical and physical properties of biological and chemical systems can be predicted from the first principles by various computational techniques (Zhang et al., 2001). Schiff bases have also been employed as ligands for the complexation of metal ions (Aydoğan et al., 2001).

The molecular structure is not planar (Fig.1); the dihedral angle between the C10—C17 benzene and the C1—C8/S1 benzothiophene ring is 61.99 (7)°. The dihedral angle between the methylenemethanamine and bezothiophene group is 3.22 (50)°. The length of the C9=N1 double bond is 1.260 (3) Å, slightly shorter than standard 1.28 Å value of a C=N double bond and consistent with related structures (Ağar et al., 2010; Ceylan et al. 2011; Dege, Şekerci et al., 2006; Genç et al. 2004; İnaç et al., 2012; Tanak et al., 2010; Tecer et al., 2010).

The C1—S1 and C8—S1 bond distances are 1.736 (3) Å and 1.717 (3) Å, respectively. The C—S bond distances are compatible with the literature (Dege, Içbudak & Adıyaman, 2006, 2007; Demirtaş et al., 2009).

The crystal structure is stabilized by an intermolecular C—H···π stacking interaction (C9—H9···Cg2ⁱ = 2.95 Å) [symmetry code (i): -x, -1/2 + y, 1 - z; Cg2 is the centroids of ring C1—C6].

Related literature top

For 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 related literature [please be more specifice, as above], 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 top

The compound (E)-1-(1-benzothiophen-3-yl)-N-(2,6-dimethylphenyl)methanimine was prepared by reflux a mixture of a solution containing 1-benzothiophene-3-carbaldehyde (0.026 g 0.16 mmol) in 20 ml e thanol and a solution containing 2,6-Dimethylaniline (0.0192 g 0.16 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 hunder reflux. The crystals of 2(E)-1-(1-benzothiophen-3-yl)-N-(2,6-dimethylphenyl)methanimine suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield % 58; m.p 75–77°C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: WinGX (Farrugia, 1997) and 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 (Dolomanov et al., 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and 50% probability displacement ellipsoids.

(E)-N-(1-Benzothiophen-3-ylmethylidene)-2,6-dimethylaniline top

Crystal data top

C₁₇H₁₅NS	F(000) = 280
M_r = 265.36	D_x = 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

Data collection top

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	R_int = 0.021
Detector resolution: 16.0454 pixels mm^-1	θ_max = 27.4°, θ_min = 3.5°
ω scans	h = −10→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −5→11
T_min = 0.965, T_max = 0.975	l = −10→13
2788 measured reflections

Refinement top

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(F_o²) + (0.0397P)² + 0.1075P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2024 reflections	Δρ_max = 0.15 e Å⁻³
174 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.10 (11)

Crystal data top

C₁₇H₁₅NS	V = 719.12 (14) Å³
M_r = 265.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.0446 (10) Å	µ = 0.21 mm⁻¹
b = 8.8031 (9) Å	T = 296 K
c = 10.2809 (10) Å	0.17 × 0.15 × 0.12 mm
β = 98.989 (11)°

Data collection top

Oxford Diffraction SuperNova (single source at offset) Eos diffractometer	2024 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	1722 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.975	R_int = 0.021
2788 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.101	Δρ_max = 0.15 e Å⁻³
S = 1.05	Δρ_min = −0.23 e Å⁻³
2024 reflections	Absolute structure: Flack (1983), 497 Friedel pairs
174 parameters	Absolute structure parameter: 0.10 (11)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅NS
M_r	265.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.0446 (10), 8.8031 (9), 10.2809 (10)
β (°)	98.989 (11)
V (Å³)	719.12 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.17 × 0.15 × 0.12

Data collection
Diffractometer	Oxford Diffraction SuperNova (single source at offset) Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.965, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	2788, 2024, 1722
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.05
No. of reflections	2024
No. of parameters	174
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.23
Absolute structure	Flack (1983), 497 Friedel pairs
Absolute structure parameter	0.10 (11)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and ORTEP-3 for Windows (Farrugia, 1997), OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, y−1/2, −z+1.

Acknowledgements

The authors thank Ondokuz Mayis University, Giresun University and Kırıkkale University, Turkey, for financial support of this study.

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