(S)-(+)-1-(1-Naphth-yl)-1-(2-thienylmethyl-ene)ethyl-amine.

The title chiral imine, C(17)H(15)NS, has been obtained via a direct synthesis route. The imine group displays the common E configuration, and is almost coplanar with the thio-phene heterocycle; the dihedral angle between the C=N-C group and the thio-phene ring is 5.1 (8)°. In contrast, the naphthyl group makes an angle of 83.79 (13)° with the thio-phene ring. The observed solid-state mol-ecular conformation is suitable for the use of this mol-ecule as an N,S-bidentate Schiff base ligand. The mol-ecular packing features double C-H⋯π inter-actions between naphthyl groups of neighboring mol-ecules, which form chains in the [100] direction. The crystal structure is further stabilized by a short C-H⋯π contact involving the methyl group and one ring of a naphthyl group. The resulting two-dimensional network is completed by a weak inter-molecular C-H(imine)⋯π(thio-phene) inter-action.

Related literature

For background to direct synthesis, see: Tanaka & Toda (2000 ▶); Jeon et al. (2005 ▶); Tovar et al. (2007 ▶). For the configuration and conformation of imines derived from thio­phene, see: Arjona et al. (1986 ▶).

Experimental

Crystal data

C17H15NS

M = 265.36

Orthorhombic,

a = 5.5274 (14) Å

b = 7.990 (2) Å

c = 31.517 (8) Å

V = 1392.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 298 K

0.50 × 0.36 × 0.04 mm

Data collection

Siemens P4 diffractometer

Absorption correction: ψ scan (XSCANS; Siemens, 1996 ▶) T min = 0.802, T max = 0.991

4462 measured reflections

2446 independent reflections

1280 reflections with I > 2σ(I)

R int = 0.045

2 standard reflections every 48 reflections intensity decay: 1.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.174

S = 1.56

2446 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 946 Friedel pairs

Flack parameter: 0.2 (2)

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022375/wn2331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022375/wn2331Isup2.hkl

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

C17H15NS	Dx = 1.266 Mg m−3
Mr = 265.36	Melting point: 345 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 68 reflections
a = 5.5274 (14) Å	θ = 4.9–11.5°
b = 7.990 (2) Å	µ = 0.22 mm−1
c = 31.517 (8) Å	T = 298 K
V = 1392.0 (6) Å3	Plate, colourless
Z = 4	0.50 × 0.36 × 0.04 mm
F(000) = 560

Siemens P4 diffractometer	1280 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 25.0°, θmin = 2.6°
ω scans	h = −6→6
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −9→9
Tmin = 0.802, Tmax = 0.991	l = −37→37
4462 measured reflections	2 standard reflections every 48 reflections
2446 independent reflections	intensity decay: 1.8%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.174	(Δ/σ)max < 0.001
S = 1.56	Δρmax = 0.31 e Å−3
2446 reflections	Δρmin = −0.39 e Å−3
174 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.046 (6)
0 constraints	Absolute structure: Flack (1983), 946 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (2)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
S1	0.0890 (3)	0.77472 (18)	0.23563 (4)	0.0851 (5)
C2	0.0387 (11)	0.7930 (7)	0.28848 (16)	0.0838 (16)
H2A	−0.0852	0.7377	0.3027	0.101*
C3	0.1958 (10)	0.8951 (7)	0.30739 (17)	0.0808 (16)
H3A	0.1920	0.9189	0.3363	0.097*
C4	0.3675 (11)	0.9631 (6)	0.27948 (16)	0.0765 (15)
H4A	0.4906	1.0359	0.2875	0.092*
C5	0.3292 (8)	0.9077 (6)	0.23880 (16)	0.0637 (12)
C6	0.4666 (10)	0.9518 (6)	0.20103 (16)	0.0709 (14)
H6A	0.5865	1.0331	0.2030	0.085*
N7	0.4278 (8)	0.8830 (5)	0.16565 (12)	0.0732 (11)
C8	0.5830 (11)	0.9318 (6)	0.12949 (14)	0.0743 (14)
H8A	0.6648	1.0374	0.1362	0.089*
C9	0.7706 (10)	0.7968 (8)	0.12312 (17)	0.0982 (19)
H9A	0.8835	0.7989	0.1462	0.147*
H9B	0.8550	0.8161	0.0970	0.147*
H9C	0.6924	0.6896	0.1221	0.147*
C10	0.4174 (10)	0.9587 (6)	0.09162 (14)	0.0679 (13)
C11	0.3745 (10)	0.8354 (6)	0.06322 (15)	0.0771 (14)
H11A	0.4564	0.7344	0.0662	0.093*
C12	0.2109 (10)	0.8542 (7)	0.02938 (16)	0.0837 (17)
H12A	0.1858	0.7662	0.0106	0.100*
C13	0.0910 (12)	0.9986 (7)	0.02414 (17)	0.0835 (16)
H13A	−0.0180	1.0099	0.0019	0.100*
C14	0.1289 (10)	1.1329 (7)	0.05212 (16)	0.0757 (14)
C15	0.0159 (12)	1.2883 (8)	0.04640 (19)	0.101 (2)
H15A	−0.0913	1.3014	0.0239	0.121*
C16	0.0570 (16)	1.4195 (9)	0.0723 (2)	0.110 (2)
H16A	−0.0224	1.5205	0.0677	0.132*
C17	0.2162 (13)	1.4043 (8)	0.1058 (2)	0.0980 (19)
H17A	0.2446	1.4950	0.1236	0.118*
C18	0.3321 (11)	1.2564 (7)	0.11269 (16)	0.0850 (16)
H18A	0.4378	1.2477	0.1355	0.102*
C19	0.2965 (10)	1.1158 (6)	0.08620 (14)	0.0702 (14)

	U11	U22	U33	U12	U13	U23
S1	0.0830 (9)	0.0941 (10)	0.0780 (9)	−0.0071 (9)	−0.0027 (8)	−0.0051 (8)
C2	0.092 (4)	0.093 (4)	0.066 (3)	0.000 (4)	0.010 (3)	0.006 (3)
C3	0.093 (4)	0.083 (4)	0.067 (3)	0.008 (4)	−0.008 (3)	−0.003 (3)
C4	0.085 (4)	0.074 (3)	0.071 (3)	−0.009 (3)	−0.001 (3)	−0.005 (3)
C5	0.058 (3)	0.063 (3)	0.070 (3)	−0.006 (2)	−0.003 (2)	−0.002 (3)
C6	0.069 (4)	0.071 (3)	0.073 (3)	−0.002 (3)	−0.005 (3)	0.000 (3)
N7	0.075 (3)	0.082 (3)	0.062 (2)	0.001 (3)	0.003 (2)	0.001 (2)
C8	0.078 (3)	0.079 (3)	0.066 (3)	0.000 (3)	0.003 (3)	0.008 (3)
C9	0.086 (4)	0.119 (5)	0.090 (4)	0.029 (4)	0.004 (3)	0.007 (4)
C10	0.073 (3)	0.069 (3)	0.062 (3)	0.002 (3)	0.001 (3)	0.003 (3)
C11	0.089 (4)	0.073 (3)	0.070 (3)	0.004 (3)	0.001 (3)	−0.001 (3)
C12	0.091 (4)	0.085 (4)	0.076 (4)	−0.002 (4)	−0.003 (3)	−0.010 (3)
C13	0.088 (4)	0.093 (4)	0.070 (3)	−0.002 (4)	−0.007 (3)	0.003 (3)
C14	0.077 (4)	0.078 (3)	0.072 (3)	0.006 (3)	0.002 (3)	0.008 (3)
C15	0.117 (5)	0.096 (4)	0.090 (4)	0.026 (4)	−0.006 (4)	0.018 (4)
C16	0.134 (6)	0.083 (4)	0.112 (5)	0.024 (5)	0.014 (5)	0.013 (4)
C17	0.117 (5)	0.078 (4)	0.099 (4)	0.007 (4)	0.017 (4)	−0.005 (4)
C18	0.097 (4)	0.077 (4)	0.081 (3)	−0.006 (4)	0.009 (3)	−0.007 (3)
C19	0.077 (3)	0.072 (3)	0.062 (3)	−0.001 (3)	0.006 (3)	0.003 (3)

S1—C2	1.695 (5)	C10—C11	1.352 (6)
S1—C5	1.703 (5)	C10—C19	1.432 (6)
C2—C3	1.332 (7)	C11—C12	1.407 (7)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.404 (7)	C12—C13	1.341 (7)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.373 (6)	C13—C14	1.405 (7)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.455 (6)	C14—C15	1.401 (7)
C6—N7	1.261 (5)	C14—C19	1.425 (7)
C6—H6A	0.9300	C15—C16	1.349 (7)
N7—C8	1.479 (6)	C15—H15A	0.9300
C8—C9	1.509 (7)	C16—C17	1.378 (9)
C8—C10	1.519 (7)	C16—H16A	0.9300
C8—H8A	0.9800	C17—C18	1.361 (8)
C9—H9A	0.9600	C17—H17A	0.9300
C9—H9B	0.9600	C18—C19	1.414 (6)
C9—H9C	0.9600	C18—H18A	0.9300
C2—S1—C5	91.0 (3)	C11—C10—C8	121.5 (5)
C3—C2—S1	112.7 (5)	C19—C10—C8	119.9 (4)
C3—C2—H2A	123.7	C10—C11—C12	122.5 (5)
S1—C2—H2A	123.7	C10—C11—H11A	118.8
C2—C3—C4	113.4 (5)	C12—C11—H11A	118.8
C2—C3—H3A	123.3	C13—C12—C11	120.2 (5)
C4—C3—H3A	123.3	C13—C12—H12A	119.9
C5—C4—C3	110.8 (5)	C11—C12—H12A	119.9
C5—C4—H4A	124.6	C12—C13—C14	120.4 (6)
C3—C4—H4A	124.6	C12—C13—H13A	119.8
C4—C5—C6	127.2 (4)	C14—C13—H13A	119.8
C4—C5—S1	112.1 (4)	C15—C14—C13	122.0 (5)
C6—C5—S1	120.6 (4)	C15—C14—C19	118.1 (5)
N7—C6—C5	121.9 (5)	C13—C14—C19	119.8 (5)
N7—C6—H6A	119.0	C16—C15—C14	122.4 (6)
C5—C6—H6A	119.0	C16—C15—H15A	118.8
C6—N7—C8	117.9 (4)	C14—C15—H15A	118.8
N7—C8—C9	108.2 (4)	C15—C16—C17	120.1 (6)
N7—C8—C10	107.0 (4)	C15—C16—H16A	119.9
C9—C8—C10	114.2 (4)	C17—C16—H16A	119.9
N7—C8—H8A	109.1	C18—C17—C16	119.9 (6)
C9—C8—H8A	109.1	C18—C17—H17A	120.0
C10—C8—H8A	109.1	C16—C17—H17A	120.0
C8—C9—H9A	109.5	C17—C18—C19	122.0 (6)
C8—C9—H9B	109.5	C17—C18—H18A	119.0
H9A—C9—H9B	109.5	C19—C18—H18A	119.0
C8—C9—H9C	109.5	C18—C19—C14	117.3 (5)
H9A—C9—H9C	109.5	C18—C19—C10	124.1 (5)
H9B—C9—H9C	109.5	C14—C19—C10	118.5 (5)
C11—C10—C19	118.5 (5)
C5—S1—C2—C3	0.2 (4)	C11—C12—C13—C14	0.6 (9)
S1—C2—C3—C4	−0.4 (6)	C12—C13—C14—C15	176.8 (5)
C2—C3—C4—C5	0.5 (7)	C12—C13—C14—C19	0.2 (9)
C3—C4—C5—C6	179.1 (5)	C13—C14—C15—C16	−177.9 (6)
C3—C4—C5—S1	−0.4 (6)	C19—C14—C15—C16	−1.3 (9)
C2—S1—C5—C4	0.1 (4)	C14—C15—C16—C17	0.5 (11)
C2—S1—C5—C6	−179.4 (4)	C15—C16—C17—C18	−0.1 (10)
C4—C5—C6—N7	174.2 (5)	C16—C17—C18—C19	0.6 (9)
S1—C5—C6—N7	−6.4 (6)	C17—C18—C19—C14	−1.4 (8)
C5—C6—N7—C8	−177.8 (4)	C17—C18—C19—C10	178.7 (5)
C6—N7—C8—C9	101.4 (5)	C15—C14—C19—C18	1.7 (7)
C6—N7—C8—C10	−135.0 (5)	C13—C14—C19—C18	178.4 (5)
N7—C8—C10—C11	−94.5 (6)	C15—C14—C19—C10	−178.5 (5)
C9—C8—C10—C11	25.3 (7)	C13—C14—C19—C10	−1.7 (7)
N7—C8—C10—C19	83.5 (6)	C11—C10—C19—C18	−177.6 (5)
C9—C8—C10—C19	−156.7 (5)	C8—C10—C19—C18	4.3 (8)
C19—C10—C11—C12	−1.9 (8)	C11—C10—C19—C14	2.5 (7)
C8—C10—C11—C12	176.1 (5)	C8—C10—C19—C14	−175.5 (5)
C10—C11—C12—C13	0.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···CgAi	0.96	2.85	3.682 (6)	145
C6—H6A···CgBii	0.93	3.03	3.891 (5)	155
C13—H13A···CgCiii	0.93	3.54	4.399 (6)	155
C15—H15A···CgAiii	0.93	3.22	4.030 (6)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯CgAi	0.96	2.85	3.682 (6)	145
C6—H6A⋯CgBii	0.93	3.03	3.891 (5)	155
C13—H13A⋯CgCiii	0.93	3.54	4.399 (6)	155
C15—H15A⋯CgAiii	0.93	3.22	4.030 (6)	147

Symmetry codes: (i) ; (ii) ; (iii) . CgA is the centroid of ring C10–C14/C19, CgB is the centroid of the thio­phene ring and CgC is the centroid of ring C14–C19.