(+)-(S)-N-[(1-Benzo­thio­phen-2-yl)methyl­idene]-1-(naphthalen-1-yl)ethyl­amine

Hernández-Téllez, G.; Portillo-Moreno, O.; Gutiérrez, R.; Rios-Merino, F.J.; Mendoza, A.

doi:10.1107/S1600536813023611

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1480

doi:10.1107/S1600536813023611

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(+)-(S)-N-[(1-Benzothiophen-2-yl)methylidene]-1-(naphthalen-1-yl)ethylamine

Guadalupe Hernández-Téllez,^a Oscar Portillo-Moreno,^a René Gutiérrez,^a Francisco J. Rios-Merino ^b and Angel Mendoza ^b ^*

^aLab. Síntesis de Complejos, Facultad de Ciencias Químicas, Benemérita, Universidad Autónoma de Puebla, PO Box 1067, 72001 Puebla, Pue., Mexico, and ^bCentro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico
^*Correspondence e-mail: angel.mendoza@correo.buap.mx

(Received 14 August 2013; accepted 21 August 2013; online 31 August 2013)

In the title compound, C₂₁H₁₇NS, the C=N double bond shows an E conformation. The dihedral angle between the mean planes of the naphthyl residue and the benzothiophene residue is 89.14 (6)°. The crystal packing is stabilized by intermolecular C—H⋯π interactions, building a ribbon structure along the a axis.

Related literature

For Schiff bases, see: García et al. (2011 ); Bernès et al. (2010 ); Jeon et al. (2005 ); Noyori (2005 ); Tanaka & Toda (2000 ).

Experimental

Crystal data

C₂₁H₁₇NS
M_r = 315.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.6423 (3) Å
b = 8.0808 (4) Å
c = 36.3864 (19) Å
V = 1659.01 (15) Å³
Z = 4
Cu Kα radiation
μ = 1.70 mm⁻¹
T = 298 K
0.93 × 0.17 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.665, T_max = 1
8690 measured reflections
2844 independent reflections
2417 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.092
S = 1.01
2844 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack parameter determined using 839 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons & Flack (2004 )
Absolute structure parameter: 0.021 (17)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1/C2/C3/C4/C9, C12/C13/C18/C19/C20/C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg1ⁱ	0.93	2.73	3.491 (4)	139
C11—H11B⋯Cg2ⁱⁱ	0.96	2.59	3.724 (5)	149
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXL2013; software used to prepare material for publication: SHELXL2013.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813023611/bt6929sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023611/bt6929Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813023611/bt6929Isup3.cml

checkCIF report

Comment top

Schiff base compounds are widely studied and used, attracting much attention in both organic synthesis and metal ion complexation. Recently, we have focused our attention on the synthesis of chiral Schiff bases by using green techniques (García et al., 2011; Bernès et al., 2010). In continuation of this work, we synthesized the title compound using the solvent-free approach because the reactions occur under mild conditions and usually require easier workup procedures and simpler equipment. Other advantages of solvent-free reactions encompass cost saving, decreased reaction times along with reduced energy consumption, as well as increased safety (Jeon et al., 2005; Noyori, 2005; Tanaka & Toda, 2000)

The C=N double bond shows an E configuration. The dihedral angle between the mean planes of the naphthyl residue and the benzothiophene residue is 90.86 (6)°. The crystal packing is stabilized by intermolecular C—H···π interactions (Table 2; cg1 is the centroid of the ring composed of S1, C2, C3 C4, and C9, cg2 is the centroid of the ring composed of C12, C13, C18, C19, C20, and C21).

Related literature top

For Schiff bases, see: García et al. (2011); Bernès et al. (2010); Jeon et al. (2005); Noyori (2005); Tanaka & Toda (2000).

Experimental top

Under solvent-free conditions, (S)-(-)-(1-naphthyl)ethylamine (0.21 g, 1.2 mmol) and benzo[b]thiophene-2-carboxaldehyde (0.20 g, 1.2 mmol) were mixed at room temperature obtaining a white solid. The crude was recrystallized from CH₂Cl₂ affording colorless crystals of the title compound. Yield 94%; mp 125–127 °C. Analysis: [α]_D²⁵ = +318 (cL, CHCl₃). FT—IR (KBr): 1621 cm-1 (C=N). ¹H NMR (400 MHz, CDCl₃/TMS) δ = 1.76, 1.78 (d, 3H, CHCH3,), 5.40, 5.42, 5.44, 5.45(q, ¹H, CH), 7.32–7.89 (m, 12 H Ar), 8.20, 8.23 (d, 1H cyclo S), 8.54 (s, 1 H, HC=N). ¹³C NMR (100 MHz, CDCl₃/TMS) δ = 24.20 (CCH₃), 64.87 (CHCH₃), 122.66 (Ar), 123.58 (Ar), 124.14 (Ar), 124.43(Ar), 125.36 (Ar), 125.66 (Ar), 125.90 (Ar), 127.47 (Ar), 127.62 (Ar), 128.91 (Ar), 130.58(Ar), 133.93 (Ar), 139.31 (Ar),140.57 (Ar), 143.16 (Ar), 153.61 (HC=N). MS—EI: m/z= 315 (M+).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXL2013 (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

(+)-(S)-N-[(1-Benzothiophen-2-yl)methylidene]-1-(naphthalen-1-yl)ethylamine top

Crystal data top

C₂₁H₁₇NS	F(000) = 664
M_r = 315.42	D_x = 1.263 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2302 reflections
a = 5.6423 (3) Å	θ = 4.8–73.7°
b = 8.0808 (4) Å	µ = 1.70 mm⁻¹
c = 36.3864 (19) Å	T = 298 K
V = 1659.01 (15) Å³	Plate, translucent colourless
Z = 4	0.93 × 0.17 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	2844 independent reflections
Graphite monochromator	2417 reflections with I > 2σ(I)
Detector resolution: 10.5564 pixels mm^-1	R_int = 0.053
ω scans	θ_max = 66.1°, θ_min = 4.9°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −6→6
T_min = 0.665, T_max = 1	k = −9→9
8690 measured reflections	l = −43→43

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0363P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.092	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.25 e Å⁻³
2844 reflections	Δρ_min = −0.18 e Å⁻³
208 parameters	Absolute structure: Flack parameter determined using 839 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack (2004)
0 restraints	Absolute structure parameter: 0.021 (17)

Crystal data top

C₂₁H₁₇NS	V = 1659.01 (15) Å³
M_r = 315.42	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.6423 (3) Å	µ = 1.70 mm⁻¹
b = 8.0808 (4) Å	T = 298 K
c = 36.3864 (19) Å	0.93 × 0.17 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur (Atlas, Gemini) diffractometer	2844 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	2417 reflections with I > 2σ(I)
T_min = 0.665, T_max = 1	R_int = 0.053
8690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.25 e Å⁻³
S = 1.01	Δρ_min = −0.18 e Å⁻³
2844 reflections	Absolute structure: Flack parameter determined using 839 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack (2004)
208 parameters	Absolute structure parameter: 0.021 (17)
0 restraints

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.

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

	x	y	z	U_iso*/U_eq
S1	0.66160 (15)	0.33795 (10)	0.20762 (2)	0.0504 (2)
C13	0.8326 (7)	0.6220 (4)	0.07300 (9)	0.0526 (8)
C5	0.8422 (8)	0.4832 (4)	0.30726 (10)	0.0559 (8)
H5	0.9665	0.5439	0.3173	0.067*
C9	0.6413 (6)	0.3627 (4)	0.25514 (9)	0.0453 (7)
C3	0.9946 (6)	0.4998 (4)	0.24067 (10)	0.0492 (8)
H3	1.1323	0.5599	0.2451	0.059*
C4	0.8335 (6)	0.4527 (4)	0.26915 (10)	0.0467 (7)
C2	0.9289 (5)	0.4490 (4)	0.20692 (11)	0.0485 (7)
C1	1.0499 (6)	0.4771 (4)	0.17269 (10)	0.0506 (8)
H1	1.182	0.546	0.1725	0.061*
C6	0.6675 (8)	0.4233 (5)	0.32929 (11)	0.0612 (9)
H6	0.6735	0.4435	0.3544	0.073*
N1	0.9833 (5)	0.4116 (4)	0.14263 (9)	0.0557 (7)
C12	0.9580 (6)	0.4687 (4)	0.07747 (10)	0.0524 (8)
C8	0.4653 (6)	0.3017 (4)	0.27776 (11)	0.0553 (9)
H8	0.3398	0.2412	0.2681	0.066*
C10	1.1270 (7)	0.4460 (5)	0.10929 (10)	0.0563 (9)
H10	1.2155	0.549	0.113	0.068*
C19	0.6218 (8)	0.5002 (6)	0.02083 (11)	0.0696 (11)
H19	0.51	0.5086	0.0021	0.083*
C18	0.6615 (8)	0.6360 (5)	0.04455 (10)	0.0626 (9)
C11	1.3029 (8)	0.3034 (6)	0.10488 (12)	0.0797 (13)
H11A	1.4038	0.2983	0.1261	0.12*
H11B	1.3975	0.3214	0.0833	0.12*
H11C	1.2177	0.2012	0.1025	0.12*
C17	0.5403 (10)	0.7867 (6)	0.04014 (15)	0.0848 (15)
H17	0.4272	0.7966	0.0217	0.102*
C7	0.4790 (7)	0.3319 (5)	0.31476 (11)	0.0611 (10)
H7	0.362	0.2913	0.3303	0.073*
C14	0.8719 (9)	0.7621 (5)	0.09573 (12)	0.0659 (11)
H14	0.9816	0.7552	0.1147	0.079*
C15	0.7523 (10)	0.9062 (6)	0.09026 (14)	0.0851 (15)
H15	0.7825	0.997	0.1052	0.102*
C20	0.7450 (8)	0.3587 (6)	0.02515 (12)	0.0700 (11)
H20	0.7182	0.2704	0.0093	0.084*
C16	0.5852 (10)	0.9180 (6)	0.06237 (15)	0.0950 (18)
H16	0.5034	1.0167	0.0589	0.114*
C21	0.9123 (7)	0.3431 (5)	0.05316 (10)	0.0610 (9)
H21	0.9956	0.2443	0.0554	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0487 (4)	0.0531 (4)	0.0493 (4)	−0.0025 (4)	−0.0075 (4)	−0.0035 (4)
C13	0.0587 (19)	0.0561 (19)	0.0431 (17)	0.0004 (18)	0.0125 (17)	0.0075 (14)
C5	0.059 (2)	0.0567 (19)	0.0522 (19)	−0.002 (2)	−0.0078 (19)	−0.0037 (16)
C9	0.0447 (16)	0.0411 (14)	0.0501 (17)	0.0052 (15)	−0.0051 (16)	0.0011 (13)
C3	0.0460 (19)	0.0482 (17)	0.054 (2)	−0.0028 (15)	−0.0055 (16)	−0.0030 (15)
C4	0.0446 (17)	0.0415 (14)	0.0541 (18)	0.0071 (16)	−0.0046 (18)	−0.0002 (14)
C2	0.0472 (17)	0.0431 (16)	0.0552 (19)	0.0040 (13)	−0.0013 (17)	0.0042 (16)
C1	0.0484 (18)	0.0518 (18)	0.051 (2)	0.0041 (15)	−0.0027 (17)	0.0030 (16)
C6	0.070 (2)	0.065 (2)	0.0485 (19)	0.005 (2)	0.002 (2)	−0.0040 (18)
N1	0.0539 (17)	0.0614 (17)	0.0517 (18)	0.0019 (15)	0.0030 (14)	0.0063 (15)
C12	0.055 (2)	0.0558 (18)	0.0461 (19)	0.0009 (17)	0.0109 (17)	0.0041 (16)
C8	0.0486 (19)	0.0497 (19)	0.068 (2)	−0.0031 (16)	−0.0031 (18)	−0.0008 (17)
C10	0.058 (2)	0.061 (2)	0.0497 (19)	−0.0035 (18)	0.0073 (18)	0.0045 (16)
C19	0.077 (3)	0.082 (3)	0.049 (2)	−0.005 (2)	−0.004 (2)	0.006 (2)
C18	0.067 (2)	0.070 (2)	0.0502 (19)	0.007 (2)	0.008 (2)	0.0127 (18)
C11	0.070 (3)	0.103 (4)	0.066 (3)	0.022 (3)	0.012 (2)	0.017 (3)
C17	0.093 (3)	0.090 (3)	0.072 (3)	0.025 (3)	−0.001 (3)	0.015 (3)
C7	0.061 (2)	0.060 (2)	0.062 (2)	0.003 (2)	0.0126 (19)	0.009 (2)
C14	0.085 (3)	0.059 (2)	0.054 (2)	0.003 (2)	0.010 (2)	0.0002 (17)
C15	0.127 (4)	0.060 (2)	0.069 (3)	0.007 (3)	0.022 (3)	0.000 (2)
C20	0.087 (3)	0.070 (3)	0.053 (2)	−0.009 (2)	0.003 (2)	−0.009 (2)
C16	0.128 (5)	0.073 (3)	0.084 (4)	0.039 (3)	0.020 (3)	0.016 (3)
C21	0.073 (2)	0.0584 (19)	0.052 (2)	0.0054 (18)	0.0099 (18)	−0.0017 (19)

Geometric parameters (Å, º) top

S1—C9	1.744 (3)	C8—H8	0.93
S1—C2	1.755 (3)	C10—C11	1.529 (6)
C13—C14	1.419 (5)	C10—H10	0.98
C13—C18	1.420 (6)	C19—C20	1.347 (6)
C13—C12	1.436 (5)	C19—C18	1.414 (6)
C5—C6	1.359 (6)	C19—H19	0.93
C5—C4	1.409 (5)	C18—C17	1.406 (6)
C5—H5	0.93	C11—H11A	0.96
C9—C8	1.380 (5)	C11—H11B	0.96
C9—C4	1.402 (5)	C11—H11C	0.96
C3—C2	1.347 (5)	C17—C16	1.358 (7)
C3—C4	1.430 (5)	C17—H17	0.93
C3—H3	0.93	C7—H7	0.93
C2—C1	1.438 (5)	C14—C15	1.361 (6)
C1—N1	1.272 (5)	C14—H14	0.93
C1—H1	0.93	C15—C16	1.388 (7)
C6—C7	1.399 (6)	C15—H15	0.93
C6—H6	0.93	C20—C21	1.395 (6)
N1—C10	1.485 (5)	C20—H20	0.93
C12—C21	1.371 (6)	C16—H16	0.93
C12—C10	1.511 (6)	C21—H21	0.93
C8—C7	1.371 (6)

C9—S1—C2	90.70 (18)	C12—C10—H10	108.9
C14—C13—C18	117.9 (4)	C11—C10—H10	108.9
C14—C13—C12	123.0 (4)	C20—C19—C18	120.4 (4)
C18—C13—C12	119.1 (3)	C20—C19—H19	119.8
C6—C5—C4	119.5 (4)	C18—C19—H19	119.8
C6—C5—H5	120.2	C17—C18—C19	121.7 (4)
C4—C5—H5	120.2	C17—C18—C13	118.9 (4)
C8—C9—C4	121.6 (3)	C19—C18—C13	119.4 (4)
C8—C9—S1	126.7 (3)	C10—C11—H11A	109.5
C4—C9—S1	111.7 (3)	C10—C11—H11B	109.5
C2—C3—C4	113.9 (3)	H11A—C11—H11B	109.5
C2—C3—H3	123.1	C10—C11—H11C	109.5
C4—C3—H3	123.1	H11A—C11—H11C	109.5
C9—C4—C5	118.4 (4)	H11B—C11—H11C	109.5
C9—C4—C3	111.5 (3)	C16—C17—C18	121.2 (5)
C5—C4—C3	130.1 (4)	C16—C17—H17	119.4
C3—C2—C1	127.6 (3)	C18—C17—H17	119.4
C3—C2—S1	112.3 (3)	C8—C7—C6	120.5 (4)
C1—C2—S1	120.1 (3)	C8—C7—H7	119.7
N1—C1—C2	122.6 (3)	C6—C7—H7	119.7
N1—C1—H1	118.7	C15—C14—C13	121.3 (5)
C2—C1—H1	118.7	C15—C14—H14	119.3
C5—C6—C7	121.1 (4)	C13—C14—H14	119.3
C5—C6—H6	119.5	C14—C15—C16	120.2 (5)
C7—C6—H6	119.5	C14—C15—H15	119.9
C1—N1—C10	117.6 (3)	C16—C15—H15	119.9
C21—C12—C13	118.2 (3)	C19—C20—C21	120.7 (4)
C21—C12—C10	121.5 (3)	C19—C20—H20	119.6
C13—C12—C10	120.2 (3)	C21—C20—H20	119.6
C7—C8—C9	118.8 (4)	C17—C16—C15	120.6 (4)
C7—C8—H8	120.6	C17—C16—H16	119.7
C9—C8—H8	120.6	C15—C16—H16	119.7
N1—C10—C12	107.7 (3)	C12—C21—C20	122.1 (4)
N1—C10—C11	107.4 (3)	C12—C21—H21	118.9
C12—C10—C11	114.9 (3)	C20—C21—H21	118.9
N1—C10—H10	108.9

C2—S1—C9—C8	−178.8 (3)	C1—N1—C10—C11	95.0 (4)
C2—S1—C9—C4	0.0 (2)	C21—C12—C10—N1	−99.0 (4)
C8—C9—C4—C5	−1.2 (5)	C13—C12—C10—N1	78.2 (4)
S1—C9—C4—C5	179.9 (3)	C21—C12—C10—C11	20.6 (5)
C8—C9—C4—C3	178.8 (3)	C13—C12—C10—C11	−162.1 (3)
S1—C9—C4—C3	−0.1 (3)	C20—C19—C18—C17	178.3 (4)
C6—C5—C4—C9	0.9 (5)	C20—C19—C18—C13	0.0 (6)
C6—C5—C4—C3	−179.1 (3)	C14—C13—C18—C17	0.2 (6)
C2—C3—C4—C9	0.2 (4)	C12—C13—C18—C17	−179.6 (4)
C2—C3—C4—C5	−179.9 (4)	C14—C13—C18—C19	178.5 (4)
C4—C3—C2—C1	179.4 (3)	C12—C13—C18—C19	−1.2 (6)
C4—C3—C2—S1	−0.2 (4)	C19—C18—C17—C16	−177.9 (5)
C9—S1—C2—C3	0.1 (3)	C13—C18—C17—C16	0.4 (7)
C9—S1—C2—C1	−179.5 (3)	C9—C8—C7—C6	0.2 (6)
C3—C2—C1—N1	173.8 (4)	C5—C6—C7—C8	−0.5 (6)
S1—C2—C1—N1	−6.7 (5)	C18—C13—C14—C15	−0.9 (6)
C4—C5—C6—C7	0.0 (6)	C12—C13—C14—C15	178.9 (4)
C2—C1—N1—C10	−178.2 (3)	C13—C14—C15—C16	1.0 (7)
C14—C13—C12—C21	−177.7 (4)	C18—C19—C20—C21	0.4 (7)
C18—C13—C12—C21	2.0 (5)	C18—C17—C16—C15	−0.3 (8)
C14—C13—C12—C10	5.0 (5)	C14—C15—C16—C17	−0.4 (8)
C18—C13—C12—C10	−175.3 (3)	C13—C12—C21—C20	−1.7 (6)
C4—C9—C8—C7	0.7 (5)	C10—C12—C21—C20	175.6 (3)
S1—C9—C8—C7	179.4 (3)	C19—C20—C21—C12	0.4 (6)
C1—N1—C10—C12	−140.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1/C2/C3/C4/C9, C12/C13/C18/C19/C20/C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ⁱ	0.93	2.73	3.491 (4)	139
C11—H11B···Cg2ⁱⁱ	0.96	2.59	3.724 (5)	149

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the S1/C2/C3/C4/C9, C12/C13/C18/C19/C20/C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ⁱ	0.93	2.73	3.491 (4)	139
C11—H11B···Cg2ⁱⁱ	0.96	2.59	3.724 (5)	149

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x+1, y, z.

Acknowledgements

Support from VIEP-UAP (GUPJ-NAT10-G) is acknowledged.

References

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Volume 69| Part 9| September 2013| Page o1480

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(+)-(S)-N-[(1-Benzo­thio­phen-2-yl)methyl­­idene]-1-(naphthalen-1-yl)ethyl­amine

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

(+)-(S)-N-[(1-Benzothiophen-2-yl)methylidene]-1-(naphthalen-1-yl)ethylamine