1,3-Bis[(-)-(S)-(1-phenyl-eth-yl)imino-meth-yl]benzene.

The title compound, C(24)H(24)N(2), is an enanti-omerically pure bis-aldimine, which displays twofold crystallographic symmetry, with two C atoms of the central benzene ring lying on the symmetry axis. The imine group is slightly twisted from the benzene core, with a dihedral angle of 12.72 (16)° between the benzene ring and the C=N-C(*) plane. The terminal phenyl rings make an angle of 66.44 (4)° and are oriented in opposite directions with respect to the benzene ring. In the crystal, mol-ecules inter-act weakly through a C-H⋯π inter-action involving the phenyl rings, and form chains along the 2(1) screw-axis in the [100] direction.

Related literature

For the structure of the analogous mol­ecule with naphthyl in place of phenyl, see: Espinosa Leija et al. (2009 ▶). For the structure of the isoformular mol­ecule with a 1,4-disubstituted benzene ring, see: García et al. (2010 ▶). For the Pd(II) and Pt(II) coordination complexes formed using the title ligand, see: Fossey et al. (2007 ▶). For background to the synthesis carried out in solvent-free conditions, see: Tanaka & Toda (2000 ▶); Jeon et al. (2005 ▶).

Experimental

Crystal data

C24H24N2

M = 340.45

Orthorhombic,

a = 21.1309 (7) Å

b = 5.6572 (2) Å

c = 8.2290 (3) Å

V = 983.71 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 130 K

0.33 × 0.26 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶) based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.980, T max = 0.991

6971 measured reflections

1161 independent reflections

1027 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 1.06

1161 reflections

154 parameters

Only H-atom coordinates refined

Δρmax = 0.09 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811021556/lr2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021556/lr2012Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811021556/lr2012Isup3.mol

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

C24H24N2	Dx = 1.149 Mg m−3
Mr = 340.45	Melting point: 353 K
Orthorhombic, P21212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 4133 reflections
a = 21.1309 (7) Å	θ = 3.6–26.0°
b = 5.6572 (2) Å	µ = 0.07 mm−1
c = 8.2290 (3) Å	T = 130 K
V = 983.71 (6) Å3	Prism, colourless
Z = 2	0.33 × 0.26 × 0.14 mm
F(000) = 364

Oxford Diffraction Xcalibur Atlas Gemini diffractometer	1161 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1027 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.4685 pixels mm-1	θmax = 26.0°, θmin = 3.7°
ω scans	h = −26→24
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009) based on expressions derived by Clark & Reid (1995)]	k = −6→6
Tmin = 0.980, Tmax = 0.991	l = −10→9
6971 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	Only H-atom coordinates refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.0095P] where P = (Fo2 + 2Fc2)/3
1161 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.17 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.08171 (5)	0.8507 (2)	0.09804 (15)	0.0334 (3)
C1	0.18464 (7)	0.9616 (3)	0.20948 (18)	0.0320 (3)
C2	0.19358 (8)	0.7590 (3)	0.3015 (2)	0.0444 (4)
H2	0.1570 (9)	0.669 (3)	0.330 (2)	0.053*
C3	0.25402 (9)	0.6851 (3)	0.3437 (2)	0.0517 (5)
H3	0.2581 (9)	0.549 (4)	0.405 (3)	0.062*
C4	0.30581 (8)	0.8153 (4)	0.2952 (2)	0.0504 (5)
H4	0.3488 (10)	0.765 (4)	0.326 (2)	0.060*
C5	0.29724 (8)	1.0147 (4)	0.2039 (2)	0.0543 (5)
H5	0.3325 (10)	1.099 (4)	0.164 (3)	0.065*
C6	0.23701 (8)	1.0880 (3)	0.1605 (2)	0.0420 (4)
H6	0.2300 (8)	1.226 (4)	0.100 (2)	0.050*
C7	0.11876 (7)	1.0481 (3)	0.16569 (19)	0.0346 (4)
H7	0.1234 (8)	1.176 (3)	0.0885 (19)	0.042*
C8	0.06895 (6)	0.8605 (3)	−0.05179 (18)	0.0320 (4)
H8	0.0837 (7)	0.997 (3)	−0.1224 (19)	0.038*
C9	0.03271 (6)	0.6758 (3)	−0.13695 (17)	0.0313 (3)
C10	0.0000	0.5000	−0.0535 (2)	0.0299 (5)
H10	0.0000	0.5000	0.068 (3)	0.036*
C11	0.0000	0.5000	−0.3906 (3)	0.0441 (6)
H11	0.0000	0.5000	−0.506 (3)	0.053*
C12	0.03173 (7)	0.6752 (3)	−0.30697 (18)	0.0398 (4)
H12	0.0545 (8)	0.797 (3)	−0.363 (2)	0.048*
C13	0.08354 (8)	1.1472 (3)	0.3116 (2)	0.0427 (4)
H13A	0.1078 (8)	1.284 (4)	0.365 (2)	0.051*
H13B	0.0793 (9)	1.021 (4)	0.393 (2)	0.051*
H13C	0.0397 (9)	1.208 (3)	0.279 (2)	0.051*

	U11	U22	U33	U12	U13	U23
N1	0.0258 (6)	0.0373 (7)	0.0370 (7)	−0.0034 (5)	0.0025 (5)	0.0064 (6)
C1	0.0324 (8)	0.0313 (7)	0.0325 (7)	−0.0046 (6)	0.0019 (6)	−0.0027 (7)
C2	0.0393 (9)	0.0360 (8)	0.0580 (11)	−0.0068 (7)	−0.0027 (8)	0.0085 (8)
C3	0.0564 (10)	0.0411 (10)	0.0578 (11)	0.0074 (9)	−0.0127 (9)	0.0024 (9)
C4	0.0371 (9)	0.0653 (12)	0.0489 (10)	0.0111 (9)	−0.0053 (8)	−0.0156 (10)
C5	0.0322 (9)	0.0736 (13)	0.0571 (11)	−0.0111 (9)	0.0038 (8)	0.0015 (11)
C6	0.0361 (9)	0.0460 (10)	0.0440 (9)	−0.0079 (7)	0.0035 (7)	0.0063 (8)
C7	0.0322 (8)	0.0310 (7)	0.0407 (8)	−0.0052 (7)	0.0028 (7)	0.0081 (7)
C8	0.0252 (7)	0.0355 (8)	0.0351 (8)	0.0052 (6)	0.0063 (6)	0.0079 (7)
C9	0.0233 (6)	0.0406 (8)	0.0301 (7)	0.0105 (7)	0.0020 (6)	0.0036 (7)
C10	0.0216 (9)	0.0413 (12)	0.0268 (10)	0.0084 (9)	0.000	0.000
C11	0.0454 (13)	0.0633 (16)	0.0236 (11)	0.0175 (12)	0.000	0.000
C12	0.0347 (8)	0.0520 (10)	0.0326 (8)	0.0119 (8)	0.0048 (7)	0.0090 (8)
C13	0.0360 (8)	0.0424 (9)	0.0496 (10)	−0.0023 (8)	0.0046 (8)	−0.0012 (9)

N1—C8	1.2633 (19)	C7—H7	0.967 (17)
N1—C7	1.4727 (19)	C8—C9	1.473 (2)
C1—C6	1.378 (2)	C8—H8	1.014 (18)
C1—C2	1.387 (2)	C9—C10	1.3920 (17)
C1—C7	1.519 (2)	C9—C12	1.399 (2)
C2—C3	1.388 (2)	C10—C9i	1.3920 (17)
C2—H2	0.96 (2)	C10—H10	1.00 (2)
C3—C4	1.378 (3)	C11—C12i	1.380 (2)
C3—H3	0.92 (2)	C11—C12	1.380 (2)
C4—C5	1.367 (3)	C11—H11	0.95 (2)
C4—H4	0.98 (2)	C12—H12	0.959 (19)
C5—C6	1.385 (2)	C13—H13A	1.02 (2)
C5—H5	0.94 (2)	C13—H13B	0.98 (2)
C6—H6	0.94 (2)	C13—H13C	1.023 (18)
C7—C13	1.520 (2)
C8—N1—C7	116.69 (13)	C1—C7—H7	107.7 (10)
C6—C1—C2	118.64 (15)	C13—C7—H7	107.0 (9)
C6—C1—C7	119.96 (14)	N1—C8—C9	122.96 (14)
C2—C1—C7	121.38 (13)	N1—C8—H8	121.8 (9)
C1—C2—C3	120.71 (17)	C9—C8—H8	115.3 (9)
C1—C2—H2	117.7 (12)	C10—C9—C12	118.95 (16)
C3—C2—H2	121.5 (11)	C10—C9—C8	122.03 (13)
C4—C3—C2	119.84 (17)	C12—C9—C8	119.01 (15)
C4—C3—H3	121.9 (12)	C9—C10—C9i	120.90 (18)
C2—C3—H3	118.2 (12)	C9—C10—H10	119.55 (9)
C5—C4—C3	119.65 (16)	C9i—C10—H10	119.55 (9)
C5—C4—H4	120.0 (12)	C12i—C11—C12	120.2 (2)
C3—C4—H4	120.4 (12)	C12i—C11—H11	119.90 (10)
C4—C5—C6	120.69 (17)	C12—C11—H11	119.90 (10)
C4—C5—H5	120.4 (12)	C11—C12—C9	120.48 (17)
C6—C5—H5	118.8 (12)	C11—C12—H12	121.4 (11)
C1—C6—C5	120.45 (16)	C9—C12—H12	118.1 (11)
C1—C6—H6	117.4 (11)	C7—C13—H13A	111.8 (10)
C5—C6—H6	122.1 (11)	C7—C13—H13B	108.4 (11)
N1—C7—C1	109.44 (12)	H13A—C13—H13B	107.4 (14)
N1—C7—C13	108.55 (12)	C7—C13—H13C	111.2 (9)
C1—C7—C13	112.35 (13)	H13A—C13—H13C	108.1 (13)
N1—C7—H7	111.8 (10)	H13B—C13—H13C	109.8 (15)
C6—C1—C2—C3	0.1 (2)	C2—C1—C7—N1	−49.69 (19)
C7—C1—C2—C3	−178.53 (16)	C6—C1—C7—C13	−107.63 (17)
C1—C2—C3—C4	0.6 (3)	C2—C1—C7—C13	70.97 (19)
C2—C3—C4—C5	−0.9 (3)	C7—N1—C8—C9	179.55 (12)
C3—C4—C5—C6	0.4 (3)	N1—C8—C9—C10	12.2 (2)
C2—C1—C6—C5	−0.6 (2)	N1—C8—C9—C12	−167.04 (14)
C7—C1—C6—C5	178.06 (16)	C12—C9—C10—C9i	0.71 (10)
C4—C5—C6—C1	0.3 (3)	C8—C9—C10—C9i	−178.53 (14)
C8—N1—C7—C1	−110.27 (15)	C12i—C11—C12—C9	0.73 (10)
C8—N1—C7—C13	126.80 (15)	C10—C9—C12—C11	−1.4 (2)
C6—C1—C7—N1	131.72 (14)	C8—C9—C12—C11	177.83 (10)

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cgii	0.92 (2)	2.97 (2)	3.7265 (18)	140.7 (18)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cgi	0.92 (2)	2.97 (2)	3.7265 (18)	140.7 (18)

Symmetry code: (i) .