(E,E,E,E)-2,3,5,6-Tetra­kis{2-[4-(dimethyl­amino)­phen­yl]ethen­yl}pyrazine

Schmitt, V.; Schollmeyer, D.; Detert, H.

doi:10.1107/S1600536811019714

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1553

doi:10.1107/S1600536811019714

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(E,E,E,E)-2,3,5,6-Tetrakis{2-[4-(dimethylamino)phenyl]ethenyl}pyrazine

Volker Schmitt,^a Dieter Schollmeyer ^a and Heiner Detert ^a ^*

^aUniversity Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
^*Correspondence e-mail: detert@uni-mainz.de

(Received 23 May 2011; accepted 24 May 2011; online 28 May 2011)

In the title compound, C₄₄H₄₈N₆, the essentially planar molecule [maximum deviation from the mean plane of the π system of 0.271 (3) Å] is located on a crystallographic centre of inversion. The almost planar (angle sums at N atoms = 357.6 and 357.1°) dimethylamino groups and short C—N bonds of the aniline groups [both 1.379 (4) Å] indicate strong electronic coupling between these groups and the central pyrazine ring.

Related literature

For similar tetrastyrylpyrazines prepared by acid- or base-catalysed condensations, see: Takahashi & Satake (1952 ). For photochemical properties of tetrastyrylpyrazines, see: Collette & Harper (2003 ); Rumi et al. (2008 ) For star-shaped chromophores, see: Detert et al. (2010 ); Detert & Sugiono (2005 ); Strehmel et al. (2003 ); Nemkovich et al. (2010 ). For a two-dimensional homologue of the linear distyrylpyrazine, see: Fischer et al. (2011 ). For cruciforms with a central benzene ring and phenylenevinylene arms, see: Niazimbetova et al. (2002 ), Hauck et al. (2007 ), Zucchero et al. (2010 ). For probes for thrombine detection, see: Yan et al. (2011 ).

Experimental

Crystal data

C₄₄H₄₈N₆
M_r = 660.88
Monoclinic, P 2₁ /c
a = 10.763 (2) Å
b = 16.6751 (19) Å
c = 10.755 (3) Å
β = 101.109 (9)°
V = 1894.1 (7) Å³
Z = 2
Cu Kα radiation
μ = 0.53 mm⁻¹
T = 193 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
3778 measured reflections
3584 independent reflections
2384 reflections with I > 2σ(I)
R_int = 0.073
3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.239
S = 1.11
3584 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019714/bt5556sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019714/bt5556Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019714/bt5556Isup3.cml

checkCIF report

Comment top

The title compound was prepared as a part of a project focusing on star-shaped chromophores and acidochromic fluorophores, see: Detert & Sugiono (2005), Strehmel et al. (2003), and Nemkovich et al. (2010). In the crystal, the cruciform adopts a a nearly planar and centrosymmetric conformation. The two linear distyrylpyrazine subunits are not equivalent, one shows small dihedral angles between the aromatic rings and the vinylene groups of -0.3 (5)° (N1—C2—C3—C4) and -177.7 (3)° (C3—C4—C5—C6). The other distyrylpyrazine axis is more distorted. Torsion angles of 8.6°(5) (N1—C14—C15—C16) and -174.4 (3)° (C15—C16—C17—C18) have been measured. Similarly, the torsion angles of 178.2 (3) (C9—C8—N11—C13), -2.2 (5)° (C7—C8—N11—C13) between the the dimethylamino group and the phenylene ring of the more planar arm are significantly smaller than those of the other distyrylpyrazine unit: 156.6 (4)° (C19—C20—N23—C24) and -26.6 (6) (C21—C20—N23—C24). Nevertheless, the strong electronic coupling between all peripheral donors and the central pyrazine acceptor is visible as short C—N bond lengths of the aniline moieties of 1.379 (4)Å for C8—N4 and for C20—N23 and the sums of the bond angles around N11 and N23 of 357 - 358°. These aniline C—N bonds are slightly longer than those found on a linear distyrylpyrazine, (1.368 (2) Å; Fischer et al. (2011)), since the acceptor strength of the pyrazine is reduced by two additional donor groups in the title compound. The packing is characterized by sheets of molecules perpendicular to the (101)-direction.

Related literature top

For similar tetrastyrylpyrazines prepared by acid- or base-catalysed condensations, see: Takahashi & Satake (1952). For photochemical properties of tetrastyrylpyrazines, see: Collette & Harper (2003); Rumi et al. (2008) For star-shaped chromophores, see: Detert et al. (2010); Detert & Sugiono (2005); Strehmel et al. (2003); Nemkovich et al. (2010). For a two-dimensional homologue of the linear distyrylpyrazine, see: Fischer et al. (2011). For cruciforms with a central benzene ring and phenylenevinylene arms, see: Niazimbetova et al. (2002), Hauck et al. (2007), Zucchero et al. (2010). For probes for thrombine detection, see: Yan et al. (2011).

Experimental top

The title compound was prepared by adding potassium tert-butylate (9.0 g, 80.4 mmol) in small portions under nitrogen to a cooled (273 K) solution of p-N,N-dimethylaminobenzaldehyde (12.0 g, 80.4 mmol) and tetramethylpyrazine (2.5 g, 18.4 mmol) in DMF (anhyd., 100 ml). Stirring at 273 K was continued for 30 min at 273 K and for 1 week at ambient temperature. Water (200 ml) was added, the precipitate was collected and lower condensation products were extracted in a Soxhlet apparatus with methanol. The residue was recrystallized from methanol/dichloromethane to yield 545 mg (5%) of a dark red solid with m. p. > 670 K.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of compound I. Displacement ellipsoids are drawn at the 50% probability level.

(E,E,E,E)-2,3,5,6-Tetrakis{2- [4-(dimethylamino)phenyl]ethenyl}pyrazine top

Crystal data top

C₄₄H₄₈N₆	F(000) = 708
M_r = 660.88	D_x = 1.159 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3 reflections
a = 10.763 (2) Å	θ = 36–47°
b = 16.6751 (19) Å	µ = 0.53 mm⁻¹
c = 10.755 (3) Å	T = 193 K
β = 101.109 (9)°	Needle, red
V = 1894.1 (7) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.073
Radiation source: rotating anode	θ_max = 69.9°, θ_min = 4.2°
Graphite monochromator	h = 0→13
ω/2θ scans	k = 0→20
3778 measured reflections	l = −13→12
3584 independent reflections	3 standard reflections every 60 min
2384 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.239	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.1104P)² + 0.8327P] where P = (F_o² + 2F_c²)/3
3584 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₄₄H₄₈N₆	V = 1894.1 (7) Å³
M_r = 660.88	Z = 2
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.763 (2) Å	µ = 0.53 mm⁻¹
b = 16.6751 (19) Å	T = 193 K
c = 10.755 (3) Å	0.30 × 0.20 × 0.10 mm
β = 101.109 (9)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.073
3778 measured reflections	3 standard reflections every 60 min
3584 independent reflections	intensity decay: 2%
2384 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.239	H-atom parameters constrained
S = 1.11	Δρ_max = 0.44 e Å⁻³
3584 reflections	Δρ_min = −0.31 e Å⁻³
230 parameters

Special details top

Experimental. ¹H-NMR (CDCl₃, 400 MHz): δ (ppm) = 7.88 (d, ³J = 15.4 Hz, 4H, 2-H ethenyl), 7.58 (d, ³J = 8.8 Hz, 8H, 2-H, 6-H phenyl), 7.38 (d, ³J = 15.4 Hz, 4H, 1-H ethenyl), 6.75 (d, ³J = 8.8 Hz, 8H, 3-H, 6-H phenyl), 3.03 (s, 24H, CH₃). ¹³C-NMR (CDCl₃, 75 MHz): δ (ppm) = 150.5 (C-4 phenyl), 144.8 (C-2, C-3, C-4, C-5 pyrazine), 134.8 (C-2 ethenyl), 128.6 (C-3, C-5 phenyl), 125.7 (C-1 phenyl), 118.5 (C-1 ethenyl), 112.2 (C-2, C-6 phenyl), 40.4 (CH₃). FD-MS: m/z (g/mol) = 220.1 (1.3 %) [M³⁺], 330.2 (10.8 %) [M²⁺], 660.2 (100 %) [M⁺]. IR (ATR): ν = 2852, 1595, 1519, 1430, 1356, 1322, 1153, 965, 946, 799 cm^-1. UV-Vis (CH₂Cl₂): λ_max = 448 nm, ε = 41446 cm²/mmol. Fluorescence (CH₂Cl₂): λ_max = 580 nm. HR-ESI-MS (g/mol): Calcd. for C₄₄H₄₈N₆: 660.3940, found: 660.3915.

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.

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

	x	y	z	U_iso*/U_eq
N1	0.4285 (2)	0.53184 (16)	0.5798 (2)	0.0526 (7)
C2	0.4847 (3)	0.57967 (17)	0.5085 (3)	0.0504 (7)
C3	0.4652 (3)	0.66661 (19)	0.5238 (3)	0.0550 (8)
H3	0.5045	0.7023	0.4744	0.066*
C4	0.3983 (3)	0.69750 (19)	0.5996 (3)	0.0546 (8)
H4	0.3625	0.6602	0.6494	0.066*
C5	0.3701 (3)	0.78186 (17)	0.6194 (3)	0.0476 (7)
C6	0.2997 (3)	0.80216 (18)	0.7090 (3)	0.0519 (8)
H6	0.2713	0.7604	0.7568	0.062*
C7	0.2687 (3)	0.87950 (19)	0.7326 (3)	0.0524 (8)
H7	0.2196	0.8901	0.7953	0.063*
C8	0.3084 (3)	0.94316 (17)	0.6651 (3)	0.0498 (7)
C9	0.3792 (3)	0.92395 (18)	0.5729 (3)	0.0548 (8)
H9	0.4075	0.9656	0.5248	0.066*
C10	0.4085 (3)	0.84511 (18)	0.5509 (3)	0.0504 (7)
H10	0.4561	0.8337	0.4873	0.060*
N11	0.2801 (3)	1.02172 (16)	0.6882 (3)	0.0671 (8)
C12	0.3545 (4)	1.08608 (19)	0.6484 (4)	0.0746 (11)
H12A	0.4442	1.0776	0.6846	0.112*
H12B	0.3270	1.1375	0.6779	0.112*
H12C	0.3424	1.0866	0.5557	0.112*
C13	0.2042 (3)	1.0400 (2)	0.7805 (4)	0.0731 (11)
H13A	0.1276	1.0068	0.7649	0.110*
H13B	0.1804	1.0968	0.7742	0.110*
H13C	0.2528	1.0289	0.8656	0.110*
C14	0.4417 (3)	0.45242 (19)	0.5724 (3)	0.0506 (7)
C15	0.3762 (3)	0.40327 (19)	0.6534 (3)	0.0556 (8)
H15	0.3938	0.3474	0.6585	0.067*
C16	0.2959 (3)	0.4313 (2)	0.7183 (3)	0.0564 (8)
H16	0.2803	0.4874	0.7116	0.068*
C17	0.2262 (3)	0.38681 (18)	0.8010 (3)	0.0490 (7)
C18	0.1360 (3)	0.4262 (2)	0.8539 (3)	0.0553 (8)
H18	0.1227	0.4818	0.8370	0.066*
C19	0.0648 (3)	0.3888 (2)	0.9297 (3)	0.0595 (8)
H19	0.0029	0.4184	0.9625	0.071*
C20	0.0826 (3)	0.3074 (2)	0.9590 (3)	0.0596 (9)
C21	0.1750 (3)	0.2668 (2)	0.9072 (3)	0.0590 (8)
H21	0.1897	0.2114	0.9253	0.071*
C22	0.2444 (3)	0.30536 (19)	0.8310 (3)	0.0546 (8)
H22	0.3064	0.2761	0.7977	0.065*
N23	0.0169 (3)	0.2693 (2)	1.0401 (4)	0.0948 (12)
C24	0.0001 (5)	0.1823 (3)	1.0311 (5)	0.1053 (17)
H24A	−0.0489	0.1683	0.9474	0.158*
H24B	−0.0452	0.1640	1.0967	0.158*
H24C	0.0831	0.1562	1.0433	0.158*
C25	−0.0672 (4)	0.3125 (3)	1.1036 (4)	0.0988 (16)
H25A	−0.0253	0.3612	1.1416	0.148*
H25B	−0.0904	0.2787	1.1702	0.148*
H25C	−0.1438	0.3271	1.0426	0.148*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0507 (14)	0.0585 (16)	0.0480 (14)	−0.0022 (12)	0.0079 (12)	−0.0034 (12)
C2	0.0549 (17)	0.0391 (16)	0.0507 (17)	−0.0038 (13)	−0.0061 (14)	0.0016 (13)
C3	0.0572 (18)	0.0496 (18)	0.0590 (19)	−0.0042 (14)	0.0131 (15)	0.0023 (15)
C4	0.0517 (17)	0.0487 (18)	0.0616 (19)	0.0010 (13)	0.0068 (15)	−0.0002 (15)
C5	0.0466 (15)	0.0420 (15)	0.0532 (17)	−0.0028 (12)	0.0071 (13)	−0.0003 (13)
C6	0.0524 (17)	0.0450 (17)	0.0604 (19)	−0.0010 (13)	0.0163 (15)	0.0080 (14)
C7	0.0548 (17)	0.0517 (17)	0.0539 (18)	0.0016 (14)	0.0189 (14)	−0.0023 (14)
C8	0.0513 (17)	0.0402 (16)	0.0555 (17)	0.0021 (13)	0.0045 (14)	−0.0014 (13)
C9	0.0589 (18)	0.0446 (17)	0.0617 (19)	−0.0071 (14)	0.0134 (15)	0.0078 (14)
C10	0.0514 (17)	0.0476 (17)	0.0551 (18)	−0.0031 (13)	0.0179 (14)	−0.0038 (14)
N11	0.081 (2)	0.0423 (15)	0.078 (2)	0.0051 (13)	0.0160 (17)	−0.0054 (14)
C12	0.097 (3)	0.0389 (18)	0.079 (2)	−0.0035 (17)	−0.006 (2)	0.0002 (16)
C13	0.068 (2)	0.063 (2)	0.083 (3)	0.0145 (17)	0.002 (2)	−0.0182 (19)
C14	0.0511 (16)	0.0507 (18)	0.0476 (16)	−0.0105 (13)	0.0033 (13)	0.0066 (14)
C15	0.0636 (19)	0.0481 (17)	0.0553 (18)	−0.0025 (15)	0.0119 (15)	0.0016 (14)
C16	0.0555 (18)	0.0558 (19)	0.0569 (19)	−0.0053 (15)	0.0086 (15)	−0.0011 (15)
C17	0.0479 (16)	0.0498 (17)	0.0484 (16)	−0.0038 (13)	0.0071 (13)	−0.0003 (13)
C18	0.0544 (18)	0.0520 (18)	0.0596 (19)	0.0074 (14)	0.0112 (15)	0.0000 (15)
C19	0.0494 (17)	0.071 (2)	0.061 (2)	0.0080 (15)	0.0173 (15)	−0.0014 (17)
C20	0.0519 (18)	0.073 (2)	0.0561 (19)	−0.0061 (16)	0.0153 (15)	0.0104 (17)
C21	0.067 (2)	0.0506 (18)	0.061 (2)	−0.0041 (15)	0.0174 (17)	0.0063 (15)
C22	0.0586 (18)	0.0529 (18)	0.0558 (18)	0.0003 (14)	0.0200 (15)	−0.0054 (14)
N23	0.089 (2)	0.107 (3)	0.101 (3)	−0.005 (2)	0.049 (2)	0.031 (2)
C24	0.091 (3)	0.110 (4)	0.114 (4)	−0.020 (3)	0.019 (3)	0.057 (3)
C25	0.062 (2)	0.168 (5)	0.074 (3)	−0.008 (3)	0.031 (2)	0.013 (3)

Geometric parameters (Å, º) top

N1—C2	1.330 (4)	C13—H13C	0.9800
N1—C14	1.336 (4)	C14—C2ⁱ	1.392 (4)
C2—C14ⁱ	1.392 (4)	C14—C15	1.471 (4)
C2—C3	1.479 (4)	C15—C16	1.299 (4)
C3—C4	1.294 (4)	C15—H15	0.9500
C3—H3	0.9500	C16—C17	1.470 (4)
C4—C5	1.463 (4)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.382 (4)
C5—C6	1.379 (4)	C17—C22	1.401 (4)
C5—C10	1.393 (4)	C18—C19	1.371 (4)
C6—C7	1.368 (4)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.398 (5)
C7—C8	1.399 (4)	C19—H19	0.9500
C7—H7	0.9500	C20—N23	1.379 (4)
C8—N11	1.379 (4)	C20—C21	1.404 (5)
C8—C9	1.399 (4)	C21—C22	1.371 (4)
C9—C10	1.383 (4)	C21—H21	0.9500
C9—H9	0.9500	C22—H22	0.9500
C10—H10	0.9500	N23—C25	1.430 (6)
N11—C13	1.434 (5)	N23—C24	1.463 (6)
N11—C12	1.452 (4)	C24—H24A	0.9800
C12—H12A	0.9800	C24—H24B	0.9800
C12—H12B	0.9800	C24—H24C	0.9800
C12—H12C	0.9800	C25—H25A	0.9800
C13—H13A	0.9800	C25—H25B	0.9800
C13—H13B	0.9800	C25—H25C	0.9800

C2—N1—C14	119.6 (3)	N1—C14—C2ⁱ	119.9 (3)
N1—C2—C14ⁱ	120.5 (3)	N1—C14—C15	116.7 (3)
N1—C2—C3	115.7 (3)	C2ⁱ—C14—C15	123.5 (3)
C14ⁱ—C2—C3	123.8 (3)	C16—C15—C14	124.2 (3)
C4—C3—C2	124.6 (3)	C16—C15—H15	117.9
C4—C3—H3	117.7	C14—C15—H15	117.9
C2—C3—H3	117.7	C15—C16—C17	127.9 (3)
C3—C4—C5	129.1 (3)	C15—C16—H16	116.1
C3—C4—H4	115.5	C17—C16—H16	116.1
C5—C4—H4	115.5	C18—C17—C22	116.4 (3)
C6—C5—C10	116.2 (3)	C18—C17—C16	119.3 (3)
C6—C5—C4	119.7 (3)	C22—C17—C16	124.3 (3)
C10—C5—C4	124.1 (3)	C19—C18—C17	123.0 (3)
C7—C6—C5	123.2 (3)	C19—C18—H18	118.5
C7—C6—H6	118.4	C17—C18—H18	118.5
C5—C6—H6	118.4	C18—C19—C20	120.5 (3)
C6—C7—C8	120.6 (3)	C18—C19—H19	119.7
C6—C7—H7	119.7	C20—C19—H19	119.7
C8—C7—H7	119.7	N23—C20—C19	121.7 (3)
N11—C8—C9	121.0 (3)	N23—C20—C21	121.2 (3)
N11—C8—C7	121.8 (3)	C19—C20—C21	117.1 (3)
C9—C8—C7	117.2 (3)	C22—C21—C20	121.3 (3)
C10—C9—C8	120.8 (3)	C22—C21—H21	119.3
C10—C9—H9	119.6	C20—C21—H21	119.3
C8—C9—H9	119.6	C21—C22—C17	121.6 (3)
C9—C10—C5	122.0 (3)	C21—C22—H22	119.2
C9—C10—H10	119.0	C17—C22—H22	119.2
C5—C10—H10	119.0	C20—N23—C25	121.3 (4)
C8—N11—C13	120.2 (3)	C20—N23—C24	119.2 (4)
C8—N11—C12	119.7 (3)	C25—N23—C24	116.7 (4)
C13—N11—C12	117.8 (3)	N23—C24—H24A	109.5
N11—C12—H12A	109.5	N23—C24—H24B	109.5
N11—C12—H12B	109.5	H24A—C24—H24B	109.5
H12A—C12—H12B	109.5	N23—C24—H24C	109.5
N11—C12—H12C	109.5	H24A—C24—H24C	109.5
H12A—C12—H12C	109.5	H24B—C24—H24C	109.5
H12B—C12—H12C	109.5	N23—C25—H25A	109.5
N11—C13—H13A	109.5	N23—C25—H25B	109.5
N11—C13—H13B	109.5	H25A—C25—H25B	109.5
H13A—C13—H13B	109.5	N23—C25—H25C	109.5
N11—C13—H13C	109.5	H25A—C25—H25C	109.5
H13A—C13—H13C	109.5	H25B—C25—H25C	109.5
H13B—C13—H13C	109.5

C14—N1—C2—C14ⁱ	−0.8 (5)	C2—N1—C14—C2ⁱ	0.7 (5)
C14—N1—C2—C3	−179.7 (3)	C2—N1—C14—C15	−179.6 (3)
N1—C2—C3—C4	−0.3 (5)	N1—C14—C15—C16	8.6 (5)
C14ⁱ—C2—C3—C4	−179.2 (3)	C2ⁱ—C14—C15—C16	−171.8 (3)
C2—C3—C4—C5	−178.2 (3)	C14—C15—C16—C17	179.9 (3)
C3—C4—C5—C6	−177.7 (3)	C15—C16—C17—C18	−174.4 (3)
C3—C4—C5—C10	3.4 (5)	C15—C16—C17—C22	5.5 (5)
C10—C5—C6—C7	−0.6 (5)	C22—C17—C18—C19	−1.4 (5)
C4—C5—C6—C7	−179.5 (3)	C16—C17—C18—C19	178.5 (3)
C5—C6—C7—C8	−0.2 (5)	C17—C18—C19—C20	1.1 (5)
C6—C7—C8—N11	−179.0 (3)	C18—C19—C20—N23	176.6 (3)
C6—C7—C8—C9	0.6 (4)	C18—C19—C20—C21	−0.3 (5)
N11—C8—C9—C10	179.3 (3)	N23—C20—C21—C22	−177.1 (3)
C7—C8—C9—C10	−0.3 (5)	C19—C20—C21—C22	−0.2 (5)
C8—C9—C10—C5	−0.5 (5)	C20—C21—C22—C17	−0.2 (5)
C6—C5—C10—C9	0.9 (4)	C18—C17—C22—C21	0.9 (5)
C4—C5—C10—C9	179.8 (3)	C16—C17—C22—C21	−178.9 (3)
C9—C8—N11—C13	178.2 (3)	C19—C20—N23—C25	−3.6 (6)
C7—C8—N11—C13	−2.2 (5)	C21—C20—N23—C25	173.2 (4)
C9—C8—N11—C12	−19.6 (5)	C19—C20—N23—C24	156.6 (4)
C7—C8—N11—C12	160.1 (3)	C21—C20—N23—C24	−26.6 (6)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₄₄H₄₈N₆
M_r	660.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	10.763 (2), 16.6751 (19), 10.755 (3)
β (°)	101.109 (9)
V (Å³)	1894.1 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3778, 3584, 2384
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.239, 1.11
No. of reflections	3584
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.31

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CORINC (Dräger & Gattow, 1971), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Acknowledgements

Financial support from the Deutsche Forschungsgemeinschaft is gratefully acknowledged.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Collette, J. C. & Harper, A. W. (2003). Proc. SPIE, 5212, 184–192. CrossRef CAS Google Scholar
Detert, H., Lehmann, M. & Meier, H. (2010). Materials, 3, 3218–3330. Web of Science CrossRef CAS Google Scholar
Detert, H. & Sugiono, E. (2005). J. Lumin. 112, 372–376. Web of Science CrossRef CAS Google Scholar
Dräger, M. & Gattow, G. (1971). Acta Chem. Scand. 25, 761–762. Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Fischer, J., Schmitt, V., Schollmeyer, D. & Detert, H. (2011). Acta Cryst. E67, o875. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hauck, M., Schoenhaber, J., Zucchero, A. J., Hardcastle, K. I., Mueller, T. J. & Bunz, U. H. F. (2007). J. Org. Chem. 72, 6714–6725. Web of Science CrossRef PubMed CAS Google Scholar
Nemkovich, N. A., Detert, H. & Schmitt, V. (2010). Chem. Phys. 378, 37–41. Web of Science CrossRef CAS Google Scholar
Niazimbetova, Z. I., Menon, A., Galvin, M. E. & Evans, D. H. (2002). J. Electroanal. Chem. 529, 43–50. CrossRef CAS Google Scholar
Rumi, M., Pond, S. J. K., Meyer-Friedrichsen, T., Zhang, Q., Bishop, M., Zhang, Y., Barlow, S., Marder, S. R. & Perry, J. W. (2008). J. Phys. Chem. C, 112, 8061–8071. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Strehmel, B., Sarker, A. M. & Detert, H. (2003). ChemPhysChem, 4, 249–259. Web of Science CrossRef PubMed CAS Google Scholar
Takahashi, T. & Satake, K. (1952). Yakugaku Zasshi, 8, 1188–1192. CAS Google Scholar
Yan, S., Huang, R., Zhou, Y., Zhang, M., Deng, M., Wang, X., Weng, X. & Zhou, X. (2011). Chem. Commun. 47, 1273–1275. CrossRef CAS Google Scholar
Zucchero, A. J., McGrier, P. & Bunz, U. H. F. (2010). Acc. Chem. Res. 43, 397–408. Web of Science CrossRef PubMed CAS Google Scholar