N,N'-Bis(2,6-diethyl-phen-yl)acenaphthyl-ene-1,2-diimine.

The title compound, C(32)H(32)N(2), has crystallographic twofold rotation symmetry, with two C atoms lying on the rotation axis. The dihedral angle between the substituted benzene ring and the naphthalene ring system is 79.8 (1)°. The crystal structure is stabilized by C-H⋯N inter-actions, which form a chain motif along the b-axis direction.

Related literature

For details and applications of acenaphthenquinone-based Schiff bases and corresponding metal complexes, see: Li et al. (2011 ▶); Hagar et al. (2010 ▶); Kovach et al. (2011 ▶); Oleinik et al. (2005 ▶); Ragaini et al. (2006 ▶); Rosa et al. (2008 ▶); Small et al. (2007 ▶); Zhou et al. (2008 ▶).

Experimental

Crystal data

C32H32N2

M = 444.60

Monoclinic,

a = 13.5134 (12) Å

b = 8.6952 (8) Å

c = 22.3532 (19) Å

β = 99.413 (1)°

V = 2591.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 185 K

0.25 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.984, T max = 0.986

7599 measured reflections

2538 independent reflections

1842 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.151

S = 1.02

2538 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052901/fy2033sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052901/fy2033Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052901/fy2033Isup3.cml

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

C32H32N2	Z = 4
Mr = 444.60	F(000) = 952
Monoclinic, C2/c	Dx = 1.140 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 13.5134 (12) Å	θ = 3.7–52.1°
b = 8.6952 (8) Å	µ = 0.07 mm−1
c = 22.3532 (19) Å	T = 185 K
β = 99.413 (1)°	Block, pale yellow
V = 2591.2 (4) Å3	0.25 × 0.24 × 0.21 mm

Bruker SMART APEX CCD diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	1842 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→14
Tmin = 0.984, Tmax = 0.986	k = −10→10
7599 measured reflections	l = −27→24

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0768P)2 + 1.7702P] where P = (Fo2 + 2Fc2)/3
2538 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. 1H NMR (300 MHz, CDCl3, 298 K) δ (p.p.m.): 1.13 (t, JH—H = 9.0 Hz, 12H, CH2CH3), 2.49 (m, 4H, CH2CH3), 2.60 (m, 4H, CH2CH3), 6.71 (d, 2H), 7.22 (m, 6H), 7.37 (t, 2H), 7.87 (d, 2H). 13C NMR (75 MHz, CDCl3, 298 K) δ (p.p.m.): 8.74, 19.58, 117.77, 118.81, 121.28, 122.94, 123.68, 124.41, 125.55, 125.86, 135.46, 143.43, 155.61 p.p.m..

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.48604 (12)	1.10939 (19)	0.30114 (7)	0.0252 (4)
C2	0.47262 (13)	1.1829 (2)	0.35360 (8)	0.0307 (4)
H2	0.4629	1.1260	0.3884	0.037*
C3	0.47366 (14)	1.3456 (2)	0.35439 (9)	0.0358 (5)
H3	0.4654	1.3973	0.3907	0.043*
C4	0.48623 (14)	1.4314 (2)	0.30468 (9)	0.0346 (5)
H4	0.4857	1.5405	0.3070	0.041*
C5	0.5000	1.3587 (3)	0.2500	0.0296 (6)
C6	0.5000	1.1977 (3)	0.2500	0.0259 (5)
C7	0.49133 (12)	0.94636 (19)	0.28284 (7)	0.0244 (4)
C8	0.46314 (14)	0.8115 (2)	0.37023 (8)	0.0290 (4)
C9	0.36277 (14)	0.8239 (2)	0.37853 (8)	0.0353 (5)
C10	0.34091 (17)	0.7996 (3)	0.43645 (10)	0.0531 (6)
H10	0.2735	0.8076	0.4432	0.064*
C11	0.41560 (19)	0.7640 (3)	0.48439 (10)	0.0664 (8)
H11	0.3997	0.7510	0.5239	0.080*
C12	0.51299 (19)	0.7475 (3)	0.47479 (10)	0.0622 (7)
H12	0.5635	0.7204	0.5078	0.075*
C13	0.53893 (15)	0.7696 (3)	0.41798 (9)	0.0426 (5)
C14	0.28009 (15)	0.8561 (3)	0.32569 (9)	0.0446 (5)
H14A	0.2972	0.9501	0.3046	0.054*
H14B	0.2170	0.8764	0.3415	0.054*
C15	0.26253 (17)	0.7249 (3)	0.28009 (10)	0.0542 (6)
H15A	0.3251	0.7018	0.2651	0.081*
H15B	0.2110	0.7550	0.2460	0.081*
H15C	0.2402	0.6334	0.2998	0.081*
C16	0.64667 (17)	0.7500 (3)	0.40762 (10)	0.0571 (7)
H16A	0.6811	0.6753	0.4374	0.068*
H16B	0.6466	0.7075	0.3665	0.068*
C17	0.7033 (2)	0.8979 (4)	0.41362 (14)	0.0786 (9)
H17A	0.6698	0.9720	0.3840	0.118*
H17B	0.7718	0.8800	0.4061	0.118*
H17C	0.7054	0.9388	0.4547	0.118*
N1	0.48669 (11)	0.81965 (16)	0.31083 (6)	0.0273 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0249 (9)	0.0236 (9)	0.0262 (9)	0.0001 (7)	0.0019 (7)	−0.0007 (7)
C2	0.0353 (10)	0.0303 (10)	0.0267 (10)	0.0014 (7)	0.0054 (8)	−0.0028 (8)
C3	0.0419 (11)	0.0314 (11)	0.0338 (11)	0.0024 (8)	0.0058 (8)	−0.0104 (8)
C4	0.0384 (11)	0.0214 (9)	0.0427 (12)	0.0017 (7)	0.0030 (8)	−0.0066 (8)
C5	0.0284 (13)	0.0230 (13)	0.0359 (15)	0.000	0.0006 (11)	0.000
C6	0.0236 (12)	0.0251 (13)	0.0281 (13)	0.000	0.0017 (10)	0.000
C7	0.0247 (8)	0.0239 (9)	0.0240 (9)	0.0000 (7)	0.0024 (7)	−0.0012 (7)
C8	0.0383 (10)	0.0267 (9)	0.0230 (9)	−0.0045 (7)	0.0077 (7)	−0.0004 (7)
C9	0.0373 (11)	0.0386 (11)	0.0308 (10)	−0.0032 (8)	0.0080 (8)	−0.0010 (8)
C10	0.0409 (12)	0.0832 (18)	0.0377 (12)	−0.0097 (11)	0.0141 (10)	−0.0014 (11)
C11	0.0583 (16)	0.117 (2)	0.0267 (12)	−0.0145 (14)	0.0150 (11)	0.0090 (13)
C12	0.0520 (15)	0.104 (2)	0.0286 (12)	−0.0064 (13)	0.0007 (10)	0.0142 (12)
C13	0.0409 (12)	0.0584 (14)	0.0282 (11)	−0.0055 (9)	0.0053 (9)	0.0060 (9)
C14	0.0333 (11)	0.0582 (14)	0.0427 (12)	0.0037 (9)	0.0069 (9)	0.0033 (10)
C15	0.0395 (12)	0.0708 (16)	0.0486 (14)	−0.0116 (11)	−0.0040 (10)	−0.0032 (12)
C16	0.0445 (13)	0.0889 (19)	0.0357 (12)	0.0050 (12)	0.0002 (10)	0.0137 (12)
C17	0.0503 (15)	0.098 (2)	0.086 (2)	−0.0047 (15)	0.0064 (14)	0.0121 (17)
N1	0.0327 (8)	0.0243 (8)	0.0248 (8)	0.0001 (6)	0.0043 (6)	0.0004 (6)

C1—C2	1.373 (2)	C10—C11	1.382 (3)
C1—C6	1.415 (2)	C10—H10	0.9500
C1—C7	1.480 (2)	C11—C12	1.375 (3)
C2—C3	1.414 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.385 (3)
C3—C4	1.372 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C16	1.521 (3)
C4—C5	1.415 (2)	C14—C15	1.522 (3)
C4—H4	0.9500	C14—H14A	0.9900
C5—C6	1.401 (3)	C14—H14B	0.9900
C5—C4i	1.415 (2)	C15—H15A	0.9800
C6—C1i	1.415 (2)	C15—H15B	0.9800
C7—N1	1.274 (2)	C15—H15C	0.9800
C7—C7i	1.524 (3)	C16—C17	1.491 (4)
C8—C13	1.401 (3)	C16—H16A	0.9900
C8—C9	1.403 (3)	C16—H16B	0.9900
C8—N1	1.417 (2)	C17—H17A	0.9800
C9—C10	1.390 (3)	C17—H17B	0.9800
C9—C14	1.513 (3)	C17—H17C	0.9800
C2—C1—C6	119.40 (17)	C10—C11—H11	120.0
C2—C1—C7	134.50 (16)	C11—C12—C13	121.4 (2)
C6—C1—C7	106.10 (15)	C11—C12—H12	119.3
C1—C2—C3	118.29 (17)	C13—C12—H12	119.3
C1—C2—H2	120.9	C12—C13—C8	118.13 (19)
C3—C2—H2	120.9	C12—C13—C16	121.09 (19)
C4—C3—C2	122.42 (17)	C8—C13—C16	120.78 (17)
C4—C3—H3	118.8	C9—C14—C15	113.50 (18)
C2—C3—H3	118.8	C9—C14—H14A	108.9
C3—C4—C5	120.52 (18)	C15—C14—H14A	108.9
C3—C4—H4	119.7	C9—C14—H14B	108.9
C5—C4—H4	119.7	C15—C14—H14B	108.9
C6—C5—C4	116.53 (12)	H14A—C14—H14B	107.7
C6—C5—C4i	116.53 (12)	C14—C15—H15A	109.5
C4—C5—C4i	126.9 (2)	C14—C15—H15B	109.5
C5—C6—C1i	122.85 (11)	H15A—C15—H15B	109.5
C5—C6—C1	122.85 (11)	C14—C15—H15C	109.5
C1i—C6—C1	114.3 (2)	H15A—C15—H15C	109.5
N1—C7—C1	133.16 (15)	H15B—C15—H15C	109.5
N1—C7—C7i	120.06 (10)	C17—C16—C13	112.3 (2)
C1—C7—C7i	106.75 (9)	C17—C16—H16A	109.1
C13—C8—C9	121.42 (16)	C13—C16—H16A	109.1
C13—C8—N1	118.61 (16)	C17—C16—H16B	109.1
C9—C8—N1	119.36 (16)	C13—C16—H16B	109.1
C10—C9—C8	117.95 (18)	H16A—C16—H16B	107.9
C10—C9—C14	120.84 (18)	C16—C17—H17A	109.5
C8—C9—C14	121.16 (16)	C16—C17—H17B	109.5
C11—C10—C9	121.1 (2)	H17A—C17—H17B	109.5
C11—C10—H10	119.4	C16—C17—H17C	109.5
C9—C10—H10	119.4	H17A—C17—H17C	109.5
C12—C11—C10	119.9 (2)	H17B—C17—H17C	109.5
C12—C11—H11	120.0	C7—N1—C8	122.72 (15)
C6—C1—C2—C3	−0.2 (2)	C13—C8—C9—C14	−174.83 (19)
C7—C1—C2—C3	178.84 (18)	N1—C8—C9—C14	−3.9 (3)
C1—C2—C3—C4	0.9 (3)	C8—C9—C10—C11	−0.1 (3)
C2—C3—C4—C5	−0.7 (3)	C14—C9—C10—C11	177.3 (2)
C3—C4—C5—C6	−0.04 (19)	C9—C10—C11—C12	−2.0 (4)
C3—C4—C5—C4i	179.96 (19)	C10—C11—C12—C13	1.6 (4)
C4—C5—C6—C1i	−179.32 (11)	C11—C12—C13—C8	0.8 (4)
C4i—C5—C6—C1i	0.68 (11)	C11—C12—C13—C16	−179.5 (2)
C4—C5—C6—C1	0.68 (11)	C9—C8—C13—C12	−2.9 (3)
C4i—C5—C6—C1	−179.32 (11)	N1—C8—C13—C12	−173.9 (2)
C2—C1—C6—C5	−0.55 (17)	C9—C8—C13—C16	177.40 (19)
C7—C1—C6—C5	−179.85 (8)	N1—C8—C13—C16	6.4 (3)
C2—C1—C6—C1i	179.45 (18)	C10—C9—C14—C15	−110.2 (2)
C7—C1—C6—C1i	0.15 (8)	C8—C9—C14—C15	67.1 (3)
C2—C1—C7—N1	−1.4 (3)	C12—C13—C16—C17	−93.2 (3)
C6—C1—C7—N1	177.72 (17)	C8—C13—C16—C17	86.5 (3)
C2—C1—C7—C7i	−179.52 (19)	C1—C7—N1—C8	7.1 (3)
C6—C1—C7—C7i	−0.4 (2)	C7i—C7—N1—C8	−175.03 (17)
C13—C8—C9—C10	2.6 (3)	C13—C8—N1—C7	−109.9 (2)
N1—C8—C9—C10	173.49 (18)	C9—C8—N1—C7	78.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N1	0.98	2.48	3.106 (3)	122.
C16—H16B···N1	0.99	2.51	2.862 (3)	101.
C4—H4···N1ii	0.95	2.43	3.379 (2)	179.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1i	0.95	2.43	3.379 (2)	179

Symmetry code: (i) .