1,2,3-Triphenyl-1,2-dihydro­quinoxaline

Edelmann, F.T.; Blaurock, S.; Lorenz, V.; Fischer, A.

doi:10.1107/S1600536808029905

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1977

doi:10.1107/S1600536808029905

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1,2,3-Triphenyl-1,2-dihydroquinoxaline

Frank T. Edelmann,^a ^* Steffen Blaurock,^a Volker Lorenz ^a and Axel Fischer ^a

^aChemisches Institut, Otto-von-Guericke-Universität Magdeburg, Universitätsplatz 2, D-39106 Magdeburg, Germany
^*Correspondence e-mail: frank.edelmann@ovgu.de

(Received 8 September 2008; accepted 17 September 2008; online 20 September 2008)

The title compound, C₂₆H₂₀N₂, first reported in 1891, was obtained as a by-product in the preparation of benzildianil from benzil and excess aniline. The dihedral angles between the fused benzene ring and the pendant phenyl rings are 17.93 (11), 53.18 (10) and 89.08 (12)°.

Related literature

For related literature, see: Bodforss (1960 ); Kehrmann & Messinger (1891 ); Sannicolò (1983 ); Lorenz et al. (1994 ); Siegfeld (1892 ).

Experimental

Crystal data

C₂₆H₂₀N₂
M_r = 360.44
Monoclinic, P 2₁ /n
a = 10.121 (2) Å
b = 10.374 (2) Å
c = 18.572 (4) Å
β = 96.49 (3)°
V = 1937.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 143 (2) K
0.40 × 0.25 × 0.20 mm

Data collection

Stoe STADI4 diffractometer
Absorption correction: none
5587 measured reflections
3413 independent reflections
2249 reflections with I > 2σ(I)
R_int = 0.038
3 standard reflections frequency: 90 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.120
S = 1.06
3413 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: DIF4 (Stoe & Cie, 1992 ); cell refinement: DIF4; data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP5 in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029905/bt2784sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808029905/bt2784Isup2.hkl

checkCIF report

Comment top

The title compound, 1,2,4-triphenyl-1,2-dihydroquinoxaline (1), was first reported as early as 1891 by Kehrmann & Messinger. In the original paper the compound was named `quinoxaline base from benzoin and phenylphenylenediamine' and was already assigned the correct structure. It was described as `magnificent uranium-yellow crystals' showing a bright blue–green fluorescence in solution (alcohols, ether, benzene) (Kehrmann & Messinger, 1891). In 1960, Bodforss used 1 and substituted derivatives thereof to prepare cationic quinoxalinium salts which in many respects resembled the well known triphenylmethane dyes (Bodforss, 1960). For example, the dimethylamino derivatives were found to give blue solutions, while the dihydroxyphenyl derivative was orange–red. The only other report on 1 found in the literature is a paper by Sannicolò entitled `New Heterocyclic Syntheses from Benzil Dianils' (Sannicolò , 1983). In this paper it was reported that 1 is formed as a by-product in the preparation of benzildianil from benzil and excess aniline in the presence of 4-toluenesulfonic acid as catalyst. Under suitable reaction conditions the isolated yield of 1 can be as high as 31% (Sannicolò, 1983). We obtained the beautiful yellow crystals of the title compound by chance in minor amounts as a by-product in the preparation of benzildianil according to the literature procedure (Siegfied et al., 1892; Lorenz et al., 1994). A crystal structure determination of revealed the presence of 1,2,4-triphenyl-1,2-dihydroquinoxaline (1) containing three adjacent phenyl substituents attached to the 1,2-dihydroquinoxaline core. With a short distance of 1.282 (3) Å the C2—N2 bond is clearly a double bond. Thus this study confirmed that Kehrmann & Messinger had assigned the correct structure of the title compound almost 120 years ago (Kehrmann & Messinger, 1891).

Related literature top

For related literature, see: Bodforss (1960); Kehrmann & Messinger (1891); Sannicolò (1983); Lorenz et al. (1994); Siegfied et al. (1892).

Experimental top

Well formed, bright yellow single crystals of the title compound were obtained as a minor by-product (less than 5% isolated yield) during a preparation of benzildianil from benzil and excess aniline according to the literature (Lorenz et al., 1994).

Computing details top

Data collection: DIF4 (Stoe & Cie, 1992); cell refinement: DIF4 (Stoe & Cie, 1992); data reduction: REDU4 (Stoe & Cie, 1992); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL96 (Sheldrick, 2008); molecular graphics: XP5 in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL96 (Sheldrick, 2008).

Figures top

Fig. 1. The molecule of the title compound in the crystal. Displacement ellipsoids represent 50% probability levels. H-Atom radii are arbitrary.

1,2,3-Triphenyl-1,2-dihydroquinoxaline top

Crystal data top

C₂₆H₂₀N₂	F(000) = 760
M_r = 360.44	D_x = 1.236 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 58 reflections
a = 10.121 (2) Å	θ = 10–11.5°
b = 10.374 (2) Å	µ = 0.07 mm⁻¹
c = 18.572 (4) Å	T = 143 K
β = 96.49 (3)°	Prism, yellow
V = 1937.4 (7) Å³	0.40 × 0.25 × 0.20 mm
Z = 4

Data collection top

Stoe STADI4 diffractometer	R_int = 0.038
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 3.1°
Graphite monochromator	h = −11→12
ω/θ scans	k = −12→6
5587 measured reflections	l = −22→0
3413 independent reflections	3 standard reflections every 90 min
2249 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0357P)² + 0.6314P] where P = (F_o² + 2F_c²)/3
3413 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₆H₂₀N₂	V = 1937.4 (7) Å³
M_r = 360.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.121 (2) Å	µ = 0.07 mm⁻¹
b = 10.374 (2) Å	T = 143 K
c = 18.572 (4) Å	0.40 × 0.25 × 0.20 mm
β = 96.49 (3)°

Data collection top

Stoe STADI4 diffractometer	R_int = 0.038
5587 measured reflections	3 standard reflections every 90 min
3413 independent reflections	intensity decay: none
2249 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.06	Δρ_max = 0.17 e Å⁻³
3413 reflections	Δρ_min = −0.20 e Å⁻³
253 parameters

Special details top

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. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.03731 (18)	0.21070 (18)	0.24908 (10)	0.0289 (5)
C1	−0.0288 (2)	0.3104 (2)	0.28694 (12)	0.0288 (5)
H1	−0.0601	0.3783	0.2508	0.035*
C2	0.0724 (2)	0.3722 (2)	0.34379 (12)	0.0284 (5)
N2	0.16822 (18)	0.30815 (19)	0.37782 (10)	0.0330 (5)
C3	0.1878 (2)	0.1800 (2)	0.35655 (13)	0.0314 (6)
C4	0.2750 (2)	0.1022 (2)	0.40081 (14)	0.0403 (6)
H4	0.3131	0.1338	0.4465	0.048*
C5	0.3068 (2)	−0.0197 (3)	0.37920 (14)	0.0429 (7)
H5	0.3662	−0.0722	0.4097	0.052*
C6	0.2513 (2)	−0.0648 (3)	0.31256 (13)	0.0389 (6)
H6	0.2745	−0.1483	0.2971	0.047*
C7	0.1631 (2)	0.0087 (2)	0.26827 (13)	0.0339 (6)
H7	0.1251	−0.0246	0.2229	0.041*
C8	0.1293 (2)	0.1322 (2)	0.28974 (12)	0.0290 (5)
C11	−0.0053 (2)	0.1892 (2)	0.17475 (12)	0.0275 (5)
C12	0.0861 (2)	0.1544 (2)	0.12738 (12)	0.0311 (5)
H12	0.1769	0.1423	0.1452	0.037*
C13	0.0448 (2)	0.1374 (2)	0.05486 (12)	0.0325 (6)
H13	0.1078	0.1140	0.0229	0.039*
C14	−0.0871 (2)	0.1540 (2)	0.02785 (13)	0.0378 (6)
H14	−0.1151	0.1413	−0.0222	0.045*
C15	−0.1772 (2)	0.1891 (2)	0.07428 (13)	0.0375 (6)
H15	−0.2677	0.2017	0.0560	0.045*
C16	−0.1375 (2)	0.2062 (2)	0.14755 (13)	0.0333 (6)
H16	−0.2010	0.2297	0.1792	0.040*
C21	−0.1490 (2)	0.2648 (2)	0.32301 (12)	0.0325 (6)
C22	−0.1641 (3)	0.1378 (3)	0.34323 (14)	0.0440 (7)
H22	−0.0993	0.0756	0.3338	0.053*
C23	−0.2732 (3)	0.1008 (3)	0.37709 (16)	0.0583 (8)
H23	−0.2823	0.0136	0.3914	0.070*
C24	−0.3685 (3)	0.1902 (4)	0.39001 (15)	0.0589 (9)
H24	−0.4438	0.1644	0.4128	0.071*
C25	−0.3549 (3)	0.3163 (3)	0.37011 (14)	0.0514 (8)
H25	−0.4202	0.3781	0.3793	0.062*
C26	−0.2458 (2)	0.3532 (3)	0.33650 (13)	0.0405 (6)
H26	−0.2370	0.4406	0.3225	0.049*
C31	0.0561 (2)	0.5091 (2)	0.36335 (12)	0.0288 (5)
C32	0.0050 (2)	0.6012 (2)	0.31318 (14)	0.0368 (6)
H32	−0.0229	0.5759	0.2647	0.044*
C34	0.0335 (2)	0.7668 (3)	0.40346 (15)	0.0429 (7)
H34	0.0259	0.8544	0.4171	0.052*
C35	0.0839 (2)	0.6766 (3)	0.45398 (14)	0.0403 (6)
H35	0.1106	0.7023	0.5025	0.048*
C36	0.0956 (2)	0.5495 (2)	0.43407 (13)	0.0339 (6)
H36	0.1312	0.4884	0.4691	0.041*
C33	−0.0058 (3)	0.7291 (2)	0.33302 (15)	0.0426 (7)
H33	−0.0402	0.7910	0.2981	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0282 (10)	0.0312 (12)	0.0270 (10)	0.0036 (9)	0.0016 (8)	−0.0023 (9)
C1	0.0295 (12)	0.0277 (13)	0.0289 (12)	0.0019 (10)	0.0021 (10)	−0.0023 (11)
C2	0.0275 (12)	0.0320 (14)	0.0261 (12)	−0.0033 (11)	0.0044 (9)	0.0001 (11)
N2	0.0305 (11)	0.0336 (12)	0.0338 (11)	0.0007 (9)	−0.0008 (9)	−0.0005 (9)
C3	0.0278 (12)	0.0299 (14)	0.0354 (13)	−0.0002 (10)	−0.0006 (10)	0.0024 (11)
C4	0.0389 (14)	0.0384 (16)	0.0410 (15)	0.0018 (12)	−0.0073 (12)	−0.0018 (12)
C5	0.0398 (15)	0.0372 (16)	0.0492 (16)	0.0059 (12)	−0.0068 (12)	0.0047 (13)
C6	0.0391 (14)	0.0346 (15)	0.0436 (15)	0.0050 (12)	0.0079 (12)	0.0024 (12)
C7	0.0338 (13)	0.0328 (15)	0.0356 (13)	0.0022 (11)	0.0066 (11)	−0.0026 (11)
C8	0.0247 (12)	0.0319 (14)	0.0308 (12)	0.0004 (10)	0.0051 (10)	0.0036 (11)
C11	0.0306 (12)	0.0236 (13)	0.0281 (12)	−0.0026 (10)	0.0028 (10)	−0.0018 (10)
C12	0.0299 (12)	0.0309 (14)	0.0321 (13)	−0.0014 (11)	0.0017 (10)	−0.0013 (11)
C13	0.0397 (14)	0.0280 (14)	0.0306 (13)	0.0011 (11)	0.0069 (11)	−0.0031 (11)
C14	0.0478 (15)	0.0353 (15)	0.0289 (13)	0.0001 (12)	−0.0009 (11)	−0.0026 (11)
C15	0.0337 (14)	0.0410 (16)	0.0355 (14)	0.0014 (12)	−0.0058 (11)	−0.0034 (12)
C16	0.0288 (13)	0.0361 (15)	0.0353 (13)	0.0014 (11)	0.0054 (10)	−0.0035 (11)
C21	0.0271 (12)	0.0416 (16)	0.0282 (13)	−0.0030 (11)	0.0011 (10)	−0.0096 (11)
C22	0.0421 (15)	0.0428 (17)	0.0489 (16)	−0.0065 (13)	0.0137 (13)	−0.0051 (14)
C23	0.0592 (19)	0.058 (2)	0.0613 (19)	−0.0188 (16)	0.0202 (16)	−0.0030 (16)
C24	0.0383 (16)	0.089 (3)	0.0526 (18)	−0.0173 (17)	0.0193 (14)	−0.0163 (18)
C25	0.0333 (15)	0.076 (2)	0.0463 (17)	0.0024 (15)	0.0094 (12)	−0.0148 (16)
C26	0.0342 (14)	0.0492 (18)	0.0378 (14)	0.0043 (12)	0.0031 (11)	−0.0073 (13)
C31	0.0245 (12)	0.0293 (14)	0.0326 (13)	−0.0010 (10)	0.0033 (10)	−0.0023 (11)
C32	0.0372 (14)	0.0348 (15)	0.0374 (14)	−0.0026 (11)	−0.0008 (11)	−0.0002 (12)
C34	0.0413 (16)	0.0297 (15)	0.0584 (18)	−0.0026 (12)	0.0084 (13)	−0.0072 (13)
C35	0.0400 (14)	0.0418 (17)	0.0399 (15)	−0.0037 (12)	0.0080 (11)	−0.0116 (13)
C36	0.0315 (13)	0.0366 (15)	0.0338 (13)	0.0006 (11)	0.0043 (11)	−0.0009 (12)
C33	0.0441 (16)	0.0301 (15)	0.0523 (17)	0.0003 (12)	−0.0003 (13)	0.0049 (13)

Geometric parameters (Å, º) top

N1—C8	1.394 (3)	C14—H14	0.9500
N1—C11	1.417 (3)	C15—C16	1.386 (3)
N1—C1	1.455 (3)	C15—H15	0.9500
C1—C2	1.527 (3)	C16—H16	0.9500
C1—C21	1.529 (3)	C21—C22	1.383 (3)
C1—H1	1.0000	C21—C26	1.385 (3)
C2—N2	1.282 (3)	C22—C23	1.385 (4)
C2—C31	1.480 (3)	C22—H22	0.9500
N2—C3	1.408 (3)	C23—C24	1.379 (4)
C3—C4	1.394 (3)	C23—H23	0.9500
C3—C8	1.404 (3)	C24—C25	1.370 (4)
C4—C5	1.376 (3)	C24—H24	0.9500
C4—H4	0.9500	C25—C26	1.383 (4)
C5—C6	1.382 (3)	C25—H25	0.9500
C5—H5	0.9500	C26—H26	0.9500
C6—C7	1.375 (3)	C31—C32	1.392 (3)
C6—H6	0.9500	C31—C36	1.393 (3)
C7—C8	1.395 (3)	C32—C33	1.385 (3)
C7—H7	0.9500	C32—H32	0.9500
C11—C16	1.387 (3)	C34—C33	1.380 (4)
C11—C12	1.394 (3)	C34—C35	1.381 (4)
C12—C13	1.376 (3)	C34—H34	0.9500
C12—H12	0.9500	C35—C36	1.379 (3)
C13—C14	1.383 (3)	C35—H35	0.9500
C13—H13	0.9500	C36—H36	0.9500
C14—C15	1.372 (3)	C33—H33	0.9500

C8—N1—C11	123.18 (19)	C14—C15—C16	120.8 (2)
C8—N1—C1	117.98 (18)	C14—C15—H15	119.6
C11—N1—C1	118.46 (18)	C16—C15—H15	119.6
N1—C1—C2	108.88 (18)	C15—C16—C11	120.1 (2)
N1—C1—C21	115.09 (19)	C15—C16—H16	119.9
C2—C1—C21	109.38 (18)	C11—C16—H16	119.9
N1—C1—H1	107.7	C22—C21—C26	118.7 (2)
C2—C1—H1	107.7	C22—C21—C1	122.1 (2)
C21—C1—H1	107.7	C26—C21—C1	119.2 (2)
N2—C2—C31	118.4 (2)	C21—C22—C23	120.4 (3)
N2—C2—C1	122.3 (2)	C21—C22—H22	119.8
C31—C2—C1	119.24 (19)	C23—C22—H22	119.8
C2—N2—C3	118.30 (19)	C24—C23—C22	120.1 (3)
C4—C3—C8	119.5 (2)	C24—C23—H23	119.9
C4—C3—N2	118.8 (2)	C22—C23—H23	119.9
C8—C3—N2	121.5 (2)	C25—C24—C23	120.1 (3)
C5—C4—C3	120.9 (2)	C25—C24—H24	119.9
C5—C4—H4	119.6	C23—C24—H24	119.9
C3—C4—H4	119.6	C24—C25—C26	119.7 (3)
C4—C5—C6	119.2 (2)	C24—C25—H25	120.1
C4—C5—H5	120.4	C26—C25—H25	120.1
C6—C5—H5	120.4	C25—C26—C21	121.0 (3)
C7—C6—C5	121.3 (2)	C25—C26—H26	119.5
C7—C6—H6	119.4	C21—C26—H26	119.5
C5—C6—H6	119.4	C32—C31—C36	118.0 (2)
C6—C7—C8	120.1 (2)	C32—C31—C2	122.5 (2)
C6—C7—H7	119.9	C36—C31—C2	119.5 (2)
C8—C7—H7	119.9	C33—C32—C31	120.9 (2)
N1—C8—C7	123.5 (2)	C33—C32—H32	119.6
N1—C8—C3	117.5 (2)	C31—C32—H32	119.6
C7—C8—C3	119.0 (2)	C33—C34—C35	119.8 (2)
C16—C11—C12	119.0 (2)	C33—C34—H34	120.1
C16—C11—N1	120.7 (2)	C35—C34—H34	120.1
C12—C11—N1	120.3 (2)	C36—C35—C34	120.1 (2)
C13—C12—C11	120.1 (2)	C36—C35—H35	119.9
C13—C12—H12	120.0	C34—C35—H35	119.9
C11—C12—H12	120.0	C35—C36—C31	121.1 (2)
C12—C13—C14	120.8 (2)	C35—C36—H36	119.5
C12—C13—H13	119.6	C31—C36—H36	119.5
C14—C13—H13	119.6	C34—C33—C32	120.0 (2)
C15—C14—C13	119.2 (2)	C34—C33—H33	120.0
C15—C14—H14	120.4	C32—C33—H33	120.0
C13—C14—H14	120.4

C8—N1—C1—C2	40.5 (3)	N1—C11—C12—C13	−178.0 (2)
C11—N1—C1—C2	−146.37 (19)	C11—C12—C13—C14	−0.2 (4)
C8—N1—C1—C21	−82.7 (2)	C12—C13—C14—C15	0.6 (4)
C11—N1—C1—C21	90.5 (2)	C13—C14—C15—C16	−0.8 (4)
N1—C1—C2—N2	−33.5 (3)	C14—C15—C16—C11	0.6 (4)
C21—C1—C2—N2	93.0 (3)	C12—C11—C16—C15	−0.2 (4)
N1—C1—C2—C31	149.66 (19)	N1—C11—C16—C15	177.9 (2)
C21—C1—C2—C31	−83.8 (2)	N1—C1—C21—C22	24.1 (3)
C31—C2—N2—C3	−176.7 (2)	C2—C1—C21—C22	−98.8 (3)
C1—C2—N2—C3	6.5 (3)	N1—C1—C21—C26	−156.4 (2)
C2—N2—C3—C4	−168.5 (2)	C2—C1—C21—C26	80.7 (3)
C2—N2—C3—C8	16.2 (3)	C26—C21—C22—C23	−0.8 (4)
C8—C3—C4—C5	1.4 (4)	C1—C21—C22—C23	178.7 (2)
N2—C3—C4—C5	−174.0 (2)	C21—C22—C23—C24	0.9 (4)
C3—C4—C5—C6	0.1 (4)	C22—C23—C24—C25	−0.7 (4)
C4—C5—C6—C7	−1.3 (4)	C23—C24—C25—C26	0.5 (4)
C5—C6—C7—C8	0.9 (4)	C24—C25—C26—C21	−0.5 (4)
C11—N1—C8—C7	−16.9 (3)	C22—C21—C26—C25	0.6 (4)
C1—N1—C8—C7	155.9 (2)	C1—C21—C26—C25	−178.9 (2)
C11—N1—C8—C3	164.7 (2)	N2—C2—C31—C32	148.6 (2)
C1—N1—C8—C3	−22.5 (3)	C1—C2—C31—C32	−34.5 (3)
C6—C7—C8—N1	−177.7 (2)	N2—C2—C31—C36	−30.0 (3)
C6—C7—C8—C3	0.7 (3)	C1—C2—C31—C36	146.9 (2)
C4—C3—C8—N1	176.6 (2)	C36—C31—C32—C33	0.2 (3)
N2—C3—C8—N1	−8.1 (3)	C2—C31—C32—C33	−178.4 (2)
C4—C3—C8—C7	−1.8 (3)	C33—C34—C35—C36	0.3 (4)
N2—C3—C8—C7	173.5 (2)	C34—C35—C36—C31	−0.6 (4)
C8—N1—C11—C16	139.9 (2)	C32—C31—C36—C35	0.3 (3)
C1—N1—C11—C16	−32.9 (3)	C2—C31—C36—C35	179.0 (2)
C8—N1—C11—C12	−42.1 (3)	C35—C34—C33—C32	0.2 (4)
C1—N1—C11—C12	145.1 (2)	C31—C32—C33—C34	−0.5 (4)
C16—C11—C12—C13	0.0 (3)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₀N₂
M_r	360.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	143
a, b, c (Å)	10.121 (2), 10.374 (2), 18.572 (4)
β (°)	96.49 (3)
V (Å³)	1937.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.25 × 0.20

Data collection
Diffractometer	Stoe STADI4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5587, 3413, 2249
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.120, 1.06
No. of reflections	3413
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: DIF4 (Stoe & Cie, 1992), REDU4 (Stoe & Cie, 1992), SHELXS86 (Sheldrick, 2008), SHELXL96 (Sheldrick, 2008), XP5 in SHELXTL (Sheldrick, 2008).

Acknowledgements

Financial support of this work by the Otto-von-Guericke-Universität Magdeburg is gratefully acknowledged.

References

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