1,4-Bis{(+)-(S)-[1-(1-naphth-yl)eth-yl]imino-meth-yl}benzene.

The title compound, C(32)H(28)N(2), is a chiral bis-imine in which both imine groups display the common E configuration. The naphthyl groups present different orientations with respect to the central core, as reflected in the dihedral angles of 21.4 (2) and 78.83 (14)° between the benzene and naphthyl mean planes, thus the highest possible C(2) local molecular symmetry is not attained. This C(1) mol-ecular conformation allows multiple C-H⋯π inter-molecular contacts involving all aromatic rings, while no π-π inter-actions are available for the stabilization of the crystal structure. The resulting packing structure is based on mol-ecules stacked along [100].

Related literature

For solvent-free synthesis in organic chemistry, see: Jeon et al. (2005 ▶); Noyori (2005 ▶); Tanaka & Toda (2000 ▶); Tovar et al. (2007 ▶). For related chiral Schiff bases constructed from a bis-substituted benzene core, see: Allouchi et al. (1994 ▶); Hamaker & Oberts (2006 ▶); Espinosa Leija et al. (2009 ▶). For the use of the enanti­omer of the title compound as a chiral dopant for liquid crystals, see: Watanabe & Fukuda (2008 ▶).

Experimental

Crystal data

C32H28N2

M = 440.56

Orthorhombic,

a = 8.391 (3) Å

b = 15.102 (5) Å

c = 19.569 (7) Å

V = 2479.6 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.6 × 0.2 × 0.2 mm

Data collection

Siemens P4 diffractometer

Absorption correction: none

6140 measured reflections

2491 independent reflections

1445 reflections with I > 2σ(I)

R int = 0.162

3 standard reflections every 97 reflections intensity decay: 2.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.163

S = 1.10

2491 reflections

310 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.18 e Å−3

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/S1600536809033455/lh2874sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033455/lh2874Isup2.hkl

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

C32H28N2	Dx = 1.180 Mg m−3
Mr = 440.56	Melting point: 438 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 100 reflections
a = 8.391 (3) Å	θ = 4.8–11.4°
b = 15.102 (5) Å	µ = 0.07 mm−1
c = 19.569 (7) Å	T = 298 K
V = 2479.6 (14) Å3	Needle, colorless
Z = 4	0.6 × 0.2 × 0.2 mm
F(000) = 936

Siemens P4 diffractometer	Rint = 0.162
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2.1°
graphite	h = −9→6
ω scans	k = −17→17
6140 measured reflections	l = −23→22
2491 independent reflections	3 standard reflections every 97 reflections
1445 reflections with I > 2σ(I)	intensity decay: 2.5%

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.384P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2491 reflections	Δρmax = 0.18 e Å−3
310 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.020 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
N1	0.1296 (6)	0.6293 (2)	0.04836 (18)	0.0727 (12)
N2	0.0862 (6)	1.0684 (2)	0.17915 (19)	0.0772 (13)
C1	0.0418 (6)	0.4748 (2)	0.0380 (2)	0.0627 (12)
C2	−0.0244 (7)	0.4806 (3)	0.1019 (2)	0.0737 (14)
H2A	−0.0007	0.5292	0.1292	0.088*
C3	−0.1255 (8)	0.4159 (3)	0.1265 (3)	0.0870 (17)
H3A	−0.1694	0.4219	0.1699	0.104*
C4	−0.1613 (8)	0.3441 (3)	0.0885 (3)	0.0872 (17)
H4A	−0.2284	0.3007	0.1061	0.105*
C5	−0.0977 (7)	0.3344 (3)	0.0223 (3)	0.0708 (13)
C6	−0.1344 (8)	0.2612 (3)	−0.0191 (3)	0.0862 (17)
H6A	−0.1986	0.2165	−0.0014	0.103*
C7	−0.0796 (8)	0.2534 (3)	−0.0837 (3)	0.0876 (17)
H7A	−0.1063	0.2042	−0.1099	0.105*
C8	0.0173 (8)	0.3197 (3)	−0.1110 (3)	0.0799 (16)
H8A	0.0528	0.3154	−0.1559	0.096*
C9	0.0604 (7)	0.3912 (3)	−0.0719 (2)	0.0708 (13)
H9A	0.1276	0.4340	−0.0903	0.085*
C10	0.0046 (6)	0.4010 (2)	−0.0043 (2)	0.0633 (12)
C11	0.1588 (7)	0.5439 (3)	0.0144 (3)	0.0733 (14)
H11A	0.1496	0.5514	−0.0352	0.088*
C12	0.3255 (7)	0.5134 (3)	0.0319 (4)	0.107 (2)
H12A	0.4009	0.5576	0.0179	0.161*
H12B	0.3477	0.4589	0.0085	0.161*
H12C	0.3337	0.5043	0.0803	0.161*
C13	0.1601 (7)	0.6977 (3)	0.0141 (2)	0.0708 (14)
H13A	0.1931	0.6908	−0.0310	0.085*
C14	0.1463 (7)	0.7871 (3)	0.0412 (2)	0.0643 (13)
C15	0.0690 (8)	0.8039 (3)	0.1020 (2)	0.0793 (16)
H15A	0.0209	0.7576	0.1257	0.095*
C16	0.0622 (8)	0.8888 (3)	0.1283 (2)	0.0784 (16)
H16A	0.0113	0.8990	0.1697	0.094*
C17	0.1308 (7)	0.9588 (3)	0.0932 (2)	0.0642 (12)
C18	0.2021 (7)	0.9427 (3)	0.0316 (2)	0.0670 (13)
H18A	0.2450	0.9894	0.0067	0.080*
C19	0.2112 (7)	0.8571 (3)	0.0060 (2)	0.0688 (13)
H19A	0.2618	0.8471	−0.0356	0.083*
C20	0.1253 (7)	1.0499 (3)	0.1189 (2)	0.0695 (14)
H20A	0.1517	1.0959	0.0894	0.083*
C21	0.0880 (7)	1.1625 (3)	0.1993 (2)	0.0719 (14)
H21A	0.1013	1.1994	0.1585	0.086*
C22	−0.0707 (8)	1.1827 (3)	0.2317 (3)	0.0884 (16)
H22A	−0.1543	1.1716	0.1994	0.133*
H22B	−0.0735	1.2437	0.2454	0.133*
H22C	−0.0853	1.1455	0.2711	0.133*
C23	0.2264 (7)	1.1784 (3)	0.2475 (2)	0.0694 (14)
C24	0.2964 (9)	1.1093 (3)	0.2803 (2)	0.0887 (17)
H24A	0.2575	1.0524	0.2729	0.106*
C25	0.4234 (11)	1.1211 (5)	0.3240 (3)	0.116 (2)
H25A	0.4690	1.0724	0.3455	0.139*
C26	0.4811 (10)	1.2020 (5)	0.3357 (3)	0.115 (2)
H26A	0.5665	1.2092	0.3655	0.138*
C27	0.4139 (9)	1.2771 (4)	0.3034 (3)	0.0903 (18)
C28	0.4724 (11)	1.3636 (5)	0.3141 (3)	0.117 (3)
H28A	0.5584	1.3721	0.3433	0.141*
C29	0.4064 (11)	1.4349 (4)	0.2826 (4)	0.115 (3)
H29A	0.4469	1.4913	0.2903	0.137*
C30	0.2805 (10)	1.4230 (4)	0.2398 (3)	0.102 (2)
H30A	0.2352	1.4718	0.2184	0.123*
C31	0.2197 (8)	1.3413 (3)	0.2279 (2)	0.0793 (15)
H31A	0.1339	1.3351	0.1981	0.095*
C32	0.2831 (7)	1.2664 (3)	0.2593 (2)	0.0710 (14)

	U11	U22	U33	U12	U13	U23
N1	0.082 (3)	0.0544 (19)	0.081 (2)	−0.010 (2)	0.003 (2)	−0.0083 (18)
N2	0.104 (4)	0.056 (2)	0.072 (2)	−0.013 (2)	0.002 (3)	−0.0035 (18)
C1	0.066 (3)	0.047 (2)	0.076 (3)	−0.007 (2)	−0.006 (3)	0.000 (2)
C2	0.086 (4)	0.061 (2)	0.074 (3)	−0.004 (3)	0.004 (3)	−0.001 (2)
C3	0.098 (5)	0.081 (3)	0.082 (3)	−0.013 (4)	0.011 (3)	0.009 (3)
C4	0.088 (4)	0.072 (3)	0.102 (4)	−0.015 (3)	0.012 (4)	0.012 (3)
C5	0.064 (3)	0.051 (2)	0.098 (3)	−0.003 (2)	−0.012 (3)	−0.001 (2)
C6	0.082 (4)	0.055 (3)	0.122 (5)	−0.007 (3)	−0.020 (4)	−0.008 (3)
C7	0.089 (4)	0.061 (3)	0.112 (4)	−0.001 (3)	−0.027 (4)	−0.019 (3)
C8	0.085 (4)	0.068 (3)	0.087 (3)	0.015 (3)	−0.020 (3)	−0.019 (3)
C9	0.074 (3)	0.060 (2)	0.078 (3)	0.001 (3)	−0.009 (3)	−0.004 (2)
C10	0.063 (3)	0.051 (2)	0.076 (3)	0.005 (2)	−0.013 (3)	−0.001 (2)
C11	0.086 (4)	0.052 (2)	0.082 (3)	−0.012 (3)	0.009 (3)	−0.013 (2)
C12	0.075 (4)	0.081 (3)	0.166 (6)	−0.016 (3)	0.017 (4)	−0.026 (4)
C13	0.081 (4)	0.058 (2)	0.074 (3)	−0.010 (3)	0.001 (3)	−0.008 (2)
C14	0.074 (4)	0.054 (2)	0.065 (2)	−0.012 (3)	−0.004 (3)	−0.003 (2)
C15	0.109 (5)	0.060 (3)	0.069 (3)	−0.020 (3)	0.012 (3)	0.001 (2)
C16	0.106 (5)	0.065 (3)	0.064 (3)	−0.012 (3)	0.013 (3)	−0.004 (2)
C17	0.070 (3)	0.053 (2)	0.070 (2)	−0.012 (2)	−0.003 (3)	−0.003 (2)
C18	0.071 (3)	0.055 (2)	0.074 (3)	−0.015 (3)	0.011 (3)	0.000 (2)
C19	0.073 (3)	0.060 (2)	0.073 (3)	−0.008 (3)	0.008 (3)	0.001 (2)
C20	0.078 (4)	0.056 (2)	0.074 (3)	−0.009 (3)	−0.001 (3)	0.001 (2)
C21	0.089 (4)	0.055 (2)	0.072 (3)	−0.003 (3)	0.001 (3)	−0.006 (2)
C22	0.085 (4)	0.082 (3)	0.099 (4)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C23	0.075 (4)	0.070 (3)	0.063 (3)	−0.004 (3)	0.003 (3)	−0.004 (2)
C24	0.113 (5)	0.076 (3)	0.077 (3)	0.009 (4)	−0.004 (4)	0.005 (3)
C25	0.126 (7)	0.123 (5)	0.098 (4)	0.022 (5)	−0.037 (5)	0.011 (4)
C26	0.104 (6)	0.159 (6)	0.082 (4)	0.009 (6)	−0.027 (4)	−0.007 (4)
C27	0.087 (5)	0.109 (4)	0.075 (3)	−0.011 (4)	−0.002 (3)	−0.018 (3)
C28	0.120 (6)	0.144 (6)	0.089 (4)	−0.056 (6)	−0.008 (4)	−0.034 (4)
C29	0.147 (8)	0.094 (4)	0.103 (4)	−0.046 (5)	0.024 (5)	−0.029 (4)
C30	0.139 (7)	0.080 (3)	0.088 (3)	−0.017 (4)	0.020 (4)	−0.018 (3)
C31	0.098 (4)	0.065 (3)	0.076 (3)	−0.005 (3)	0.006 (3)	−0.013 (2)
C32	0.076 (4)	0.073 (3)	0.064 (3)	−0.005 (3)	0.003 (3)	−0.014 (2)

N1—C13	1.257 (5)	C15—H15A	0.9300
N1—C11	1.472 (5)	C16—C17	1.386 (6)
N2—C20	1.255 (5)	C16—H16A	0.9300
N2—C21	1.476 (5)	C17—C18	1.367 (6)
C1—C2	1.371 (6)	C17—C20	1.465 (5)
C1—C10	1.423 (5)	C18—C19	1.388 (5)
C1—C11	1.505 (6)	C18—H18A	0.9300
C2—C3	1.380 (7)	C19—H19A	0.9300
C2—H2A	0.9300	C20—H20A	0.9300
C3—C4	1.350 (7)	C21—C22	1.506 (8)
C3—H3A	0.9300	C21—C23	1.515 (7)
C4—C5	1.409 (7)	C21—H21A	0.9800
C4—H4A	0.9300	C22—H22A	0.9600
C5—C6	1.406 (6)	C22—H22B	0.9600
C5—C10	1.420 (6)	C22—H22C	0.9600
C6—C7	1.350 (8)	C23—C24	1.359 (7)
C6—H6A	0.9300	C23—C32	1.430 (6)
C7—C8	1.396 (7)	C24—C25	1.378 (10)
C7—H7A	0.9300	C24—H24A	0.9300
C8—C9	1.371 (6)	C25—C26	1.335 (8)
C8—H8A	0.9300	C25—H25A	0.9300
C9—C10	1.412 (6)	C26—C27	1.415 (8)
C9—H9A	0.9300	C26—H26A	0.9300
C11—C12	1.511 (8)	C27—C32	1.406 (8)
C11—H11A	0.9800	C27—C28	1.412 (8)
C12—H12A	0.9600	C28—C29	1.358 (9)
C12—H12B	0.9600	C28—H28A	0.9300
C12—H12C	0.9600	C29—C30	1.360 (11)
C13—C14	1.456 (5)	C29—H29A	0.9300
C13—H13A	0.9300	C30—C31	1.355 (7)
C14—C19	1.375 (6)	C30—H30A	0.9300
C14—C15	1.379 (6)	C31—C32	1.393 (7)
C15—C16	1.383 (6)	C31—H31A	0.9300
C13—N1—C11	116.4 (4)	C17—C16—H16A	119.8
C20—N2—C21	117.5 (4)	C18—C17—C16	118.8 (4)
C2—C1—C10	119.4 (4)	C18—C17—C20	118.9 (4)
C2—C1—C11	120.0 (4)	C16—C17—C20	122.2 (4)
C10—C1—C11	120.5 (4)	C17—C18—C19	120.6 (4)
C1—C2—C3	121.5 (4)	C17—C18—H18A	119.7
C1—C2—H2A	119.2	C19—C18—H18A	119.7
C3—C2—H2A	119.2	C14—C19—C18	120.9 (4)
C4—C3—C2	120.9 (5)	C14—C19—H19A	119.6
C4—C3—H3A	119.6	C18—C19—H19A	119.6
C2—C3—H3A	119.6	N2—C20—C17	122.6 (4)
C3—C4—C5	120.4 (5)	N2—C20—H20A	118.7
C3—C4—H4A	119.8	C17—C20—H20A	118.7
C5—C4—H4A	119.8	N2—C21—C22	107.3 (5)
C6—C5—C4	121.9 (5)	N2—C21—C23	109.1 (4)
C6—C5—C10	118.6 (5)	C22—C21—C23	112.5 (4)
C4—C5—C10	119.5 (4)	N2—C21—H21A	109.3
C7—C6—C5	122.3 (5)	C22—C21—H21A	109.3
C7—C6—H6A	118.9	C23—C21—H21A	109.3
C5—C6—H6A	118.9	C21—C22—H22A	109.5
C6—C7—C8	119.6 (5)	C21—C22—H22B	109.5
C6—C7—H7A	120.2	H22A—C22—H22B	109.5
C8—C7—H7A	120.2	C21—C22—H22C	109.5
C9—C8—C7	120.4 (5)	H22A—C22—H22C	109.5
C9—C8—H8A	119.8	H22B—C22—H22C	109.5
C7—C8—H8A	119.8	C24—C23—C32	119.6 (5)
C8—C9—C10	121.2 (5)	C24—C23—C21	120.2 (4)
C8—C9—H9A	119.4	C32—C23—C21	120.2 (4)
C10—C9—H9A	119.4	C23—C24—C25	121.8 (6)
C9—C10—C5	118.0 (4)	C23—C24—H24A	119.1
C9—C10—C1	123.7 (4)	C25—C24—H24A	119.1
C5—C10—C1	118.3 (4)	C26—C25—C24	120.4 (6)
N1—C11—C1	111.1 (4)	C26—C25—H25A	119.8
N1—C11—C12	108.6 (5)	C24—C25—H25A	119.8
C1—C11—C12	108.9 (4)	C25—C26—C27	120.8 (6)
N1—C11—H11A	109.4	C25—C26—H26A	119.6
C1—C11—H11A	109.4	C27—C26—H26A	119.6
C12—C11—H11A	109.4	C32—C27—C28	117.9 (6)
C11—C12—H12A	109.5	C32—C27—C26	119.6 (5)
C11—C12—H12B	109.5	C28—C27—C26	122.5 (7)
H12A—C12—H12B	109.5	C29—C28—C27	121.6 (6)
C11—C12—H12C	109.5	C29—C28—H28A	119.2
H12A—C12—H12C	109.5	C27—C28—H28A	119.2
H12B—C12—H12C	109.5	C28—C29—C30	119.5 (6)
N1—C13—C14	123.4 (4)	C28—C29—H29A	120.3
N1—C13—H13A	118.3	C30—C29—H29A	120.3
C14—C13—H13A	118.3	C31—C30—C29	121.3 (7)
C19—C14—C15	118.5 (4)	C31—C30—H30A	119.4
C19—C14—C13	119.9 (4)	C29—C30—H30A	119.4
C15—C14—C13	121.5 (4)	C30—C31—C32	121.3 (6)
C14—C15—C16	120.7 (4)	C30—C31—H31A	119.4
C14—C15—H15A	119.7	C32—C31—H31A	119.4
C16—C15—H15A	119.7	C31—C32—C27	118.4 (5)
C15—C16—C17	120.5 (4)	C31—C32—C23	123.8 (5)
C15—C16—H16A	119.8	C27—C32—C23	117.8 (5)
C10—C1—C2—C3	0.6 (8)	C16—C17—C18—C19	−2.5 (8)
C11—C1—C2—C3	−176.5 (5)	C20—C17—C18—C19	179.3 (5)
C1—C2—C3—C4	0.6 (9)	C15—C14—C19—C18	1.3 (8)
C2—C3—C4—C5	−0.9 (9)	C13—C14—C19—C18	−178.7 (5)
C3—C4—C5—C6	−179.0 (6)	C17—C18—C19—C14	1.2 (8)
C3—C4—C5—C10	0.0 (8)	C21—N2—C20—C17	178.9 (5)
C4—C5—C6—C7	177.0 (6)	C18—C17—C20—N2	−168.0 (5)
C10—C5—C6—C7	−2.0 (8)	C16—C17—C20—N2	13.9 (9)
C5—C6—C7—C8	0.2 (9)	C20—N2—C21—C22	129.1 (6)
C6—C7—C8—C9	1.8 (8)	C20—N2—C21—C23	−108.7 (5)
C7—C8—C9—C10	−1.9 (8)	N2—C21—C23—C24	−18.5 (7)
C8—C9—C10—C5	0.1 (7)	C22—C21—C23—C24	100.5 (6)
C8—C9—C10—C1	−178.3 (5)	N2—C21—C23—C32	162.1 (5)
C6—C5—C10—C9	1.8 (7)	C22—C21—C23—C32	−78.9 (6)
C4—C5—C10—C9	−177.2 (5)	C32—C23—C24—C25	−1.2 (9)
C6—C5—C10—C1	−179.8 (5)	C21—C23—C24—C25	179.5 (6)
C4—C5—C10—C1	1.2 (7)	C23—C24—C25—C26	0.3 (11)
C2—C1—C10—C9	176.8 (5)	C24—C25—C26—C27	−0.2 (11)
C11—C1—C10—C9	−6.1 (7)	C25—C26—C27—C32	1.0 (10)
C2—C1—C10—C5	−1.5 (7)	C25—C26—C27—C28	−179.5 (7)
C11—C1—C10—C5	175.5 (4)	C32—C27—C28—C29	−0.4 (10)
C13—N1—C11—C1	−147.5 (5)	C26—C27—C28—C29	−180.0 (7)
C13—N1—C11—C12	92.8 (6)	C27—C28—C29—C30	0.1 (11)
C2—C1—C11—N1	−27.7 (7)	C28—C29—C30—C31	−0.1 (10)
C10—C1—C11—N1	155.2 (4)	C29—C30—C31—C32	0.4 (9)
C2—C1—C11—C12	91.8 (6)	C30—C31—C32—C27	−0.7 (8)
C10—C1—C11—C12	−85.2 (6)	C30—C31—C32—C23	−178.5 (5)
C11—N1—C13—C14	−176.5 (6)	C28—C27—C32—C31	0.7 (8)
N1—C13—C14—C19	167.0 (5)	C26—C27—C32—C31	−179.7 (6)
N1—C13—C14—C15	−13.0 (9)	C28—C27—C32—C23	178.7 (5)
C19—C14—C15—C16	−2.4 (9)	C26—C27—C32—C23	−1.8 (8)
C13—C14—C15—C16	177.6 (6)	C24—C23—C32—C31	179.7 (6)
C14—C15—C16—C17	1.1 (9)	C21—C23—C32—C31	−0.9 (8)
C15—C16—C17—C18	1.4 (9)	C24—C23—C32—C27	1.9 (7)
C15—C16—C17—C20	179.5 (6)	C21—C23—C32—C27	−178.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1i	0.93	3.29	4.042 (6)	140
C8—H8A···Cg2i	0.93	3.14	3.797 (5)	129
C12—H12A···Cg3ii	0.96	2.79	3.677 (6)	154
C18—H18A···Cg4ii	0.93	2.62	3.520 (5)	163
C20—H20A···Cg5ii	0.93	2.98	3.681 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯Cg3i	0.96	2.79	3.677 (6)	154
C18—H18A⋯Cg4i	0.93	2.62	3.520 (5)	163
C20—H20A⋯Cg5i	0.93	2.98	3.681 (5)	133

Symmetry code: (i) . Cg1 is the centroid of ring C27–C32, Cg2 is the centroid of ring C23–C27/C32, Cg3 is the centroid of ring C14–C19, Cg4 is the centroid of ring C1–C5/C10 and Cg5 is the centroid of ring C5–C10.