(+)-(S)-N-[(1-Benzo-thio-phen-2-yl)methyl-idene]-1-(naphthalen-1-yl)ethyl-amine.

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 benzo-thio-phene residue is 89.14 (6)°. The crystal packing is stabilized by inter-molecular C-H⋯π inter-actions, 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 = 315.42

Orthorhombic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.092

S = 1.01

2844 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −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)

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813023611/bt6929sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023611/bt6929Isup3.cml

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

C21H17NS	F(000) = 664
Mr = 315.42	Dx = 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

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

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(Fo2) + (0.0363P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.25 e Å−3
2844 reflections	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .