Acta Cryst. (2014). E70, o16 [ doi:10.1107/S1600536813032698 ]
In the title compound, C24H19N, the dimethylamino group is inclined to the benzene ring by 2.81 (9)°. Their mean plane makes a dihedral angle of 64.12 (2)° with the mean plane of the pyrene ring system [r.m.s. deviation = 0.031 (1) Å]. In the crystal, molecules are linked via C-H interactions, which connect neighbouring molecules into columns along the c axis.
Commercially available 1-aminopyrene after diazotization reaction was coupled with N,N-dimethylaniline according to the previously reported procedure (Dewar & Mole, 1956; Norman et al., 1958). The crude product was then purified on an aluminium oxide column with a mixture of cyclohexane/toluene as eluent and applying HPLC. Block-like colourless crystals of the title compound were obtained by crystallization from ethyl acetate/diethyl ether (2:1) by slow evaporation.
The C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.95 and 0.98 Å for CH and CH3 H-atoms, respectively, with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.
Data collection: XDS (Kabsch, 1993); cell refinement: XDS (Kabsch, 1993); data reduction: XDS (Kabsch, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).
C24H19N | F(000) = 680 |
Mr = 321.40 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.600 Å |
a = 6.1270 (12) Å | Cell parameters from 2549 reflections |
b = 30.686 (6) Å | θ = 2.5–26.7° |
c = 9.478 (3) Å | µ = 0.08 mm−1 |
β = 113.35 (2)° | T = 100 K |
V = 1636.0 (8) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.15 × 0.10 mm |
Huber diffractometer with a Mar CCD detector | 4806 reflections with I > 2σ(I) |
Radiation source: synchrotron | Rint = 0.063 |
φ and ω scan | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −8→9 |
Tmin = 0.978, Tmax = 0.993 | k = −44→45 |
47866 measured reflections | l = −14→14 |
5872 independent 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0707P)2 + 0.2446P]
where P = (Fo2 + 2Fc2)/3 |
5872 reflections | (Δ/σ)max < 0.001 |
228 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C24H19N | V = 1636.0 (8) Å3 |
Mr = 321.40 | Z = 4 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.600 Å |
a = 6.1270 (12) Å | µ = 0.08 mm−1 |
b = 30.686 (6) Å | T = 100 K |
c = 9.478 (3) Å | 0.30 × 0.15 × 0.10 mm |
β = 113.35 (2)° |
Huber diffractometer with a Mar CCD detector | 5872 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4806 reflections with I > 2σ(I) |
Tmin = 0.978, Tmax = 0.993 | Rint = 0.063 |
47866 measured reflections | θmax = 27.0° |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.135 | Δρmax = 0.40 e Å−3 |
S = 1.08 | Δρmin = −0.23 e Å−3 |
5872 reflections | Absolute structure: ? |
228 parameters | Absolute structure parameter: ? |
0 restraints | Rogers parameter: ? |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | ||
N1 | 0.83448 (13) | 0.39409 (2) | 0.82389 (9) | 0.0218 (2) | |
C1 | 0.89994 (14) | 0.35082 (3) | 0.85268 (9) | 0.0180 (2) | |
C2 | 1.05726 (15) | 0.33134 (3) | 0.79588 (10) | 0.0198 (2) | |
C3 | 1.11516 (15) | 0.28751 (3) | 0.82171 (10) | 0.0199 (2) | |
C4 | 1.01916 (14) | 0.26098 (3) | 0.90243 (9) | 0.0187 (2) | |
C5 | 0.86753 (15) | 0.28065 (3) | 0.96166 (10) | 0.0201 (2) | |
C6 | 0.80935 (15) | 0.32448 (3) | 0.93886 (10) | 0.0197 (2) | |
C7 | 1.07388 (14) | 0.21366 (3) | 0.92100 (9) | 0.0184 (2) | |
C8 | 1.30833 (15) | 0.19960 (3) | 0.99985 (10) | 0.0207 (2) | |
C9 | 1.36781 (15) | 0.15583 (3) | 1.01804 (10) | 0.0214 (2) | |
C10 | 1.19330 (14) | 0.12377 (3) | 0.95599 (9) | 0.0193 (2) | |
C11 | 1.24827 (15) | 0.07810 (3) | 0.97107 (10) | 0.0222 (2) | |
C12 | 1.07813 (16) | 0.04746 (3) | 0.90639 (10) | 0.0226 (2) | |
C13 | 0.83518 (15) | 0.05968 (3) | 0.81869 (10) | 0.0207 (2) | |
C14 | 0.65740 (17) | 0.02878 (3) | 0.74593 (11) | 0.0250 (2) | |
C15 | 0.42488 (17) | 0.04181 (3) | 0.66041 (11) | 0.0266 (2) | |
C16 | 0.36320 (16) | 0.08558 (3) | 0.64636 (10) | 0.0236 (2) | |
C17 | 0.53509 (15) | 0.11768 (3) | 0.71636 (9) | 0.0194 (2) | |
C18 | 0.77440 (14) | 0.10477 (3) | 0.80332 (9) | 0.0184 (2) | |
C19 | 0.95341 (14) | 0.13704 (3) | 0.87271 (9) | 0.0176 (2) | |
C20 | 0.89286 (14) | 0.18211 (3) | 0.85573 (9) | 0.0176 (2) | |
C21 | 0.64894 (14) | 0.19381 (3) | 0.76703 (10) | 0.0193 (2) | |
C22 | 0.47894 (14) | 0.16319 (3) | 0.70109 (10) | 0.0204 (2) | |
C23 | 0.94074 (16) | 0.42139 (3) | 0.74417 (11) | 0.0248 (2) | |
C24 | 0.67405 (16) | 0.41312 (3) | 0.88441 (11) | 0.0249 (2) | |
H2 | 1.12420 | 0.34840 | 0.73940 | 0.0240* | |
H3 | 1.22310 | 0.27520 | 0.78340 | 0.0240* | |
H5 | 0.80260 | 0.26350 | 1.01910 | 0.0240* | |
H6 | 0.70730 | 0.33690 | 0.98170 | 0.0240* | |
H8 | 1.43040 | 0.22070 | 1.04220 | 0.0250* | |
H9 | 1.52870 | 0.14750 | 1.07320 | 0.0260* | |
H11 | 1.40770 | 0.06910 | 1.02770 | 0.0270* | |
H12 | 1.12010 | 0.01750 | 0.91920 | 0.0270* | |
H14 | 0.69630 | −0.00130 | 0.75520 | 0.0300* | |
H15 | 0.30680 | 0.02050 | 0.61100 | 0.0320* | |
H16 | 0.20290 | 0.09390 | 0.58870 | 0.0280* | |
H21 | 0.60590 | 0.22370 | 0.75430 | 0.0230* | |
H22 | 0.31970 | 0.17210 | 0.64370 | 0.0240* | |
H52A | 0.90310 | 0.40970 | 0.64090 | 0.0370* | |
H52B | 1.11360 | 0.42200 | 0.80130 | 0.0370* | |
H52C | 0.87760 | 0.45110 | 0.73620 | 0.0370* | |
H52D | 0.63160 | 0.44270 | 0.84360 | 0.0370* | |
H52E | 0.75170 | 0.41430 | 0.99680 | 0.0370* | |
H52F | 0.52990 | 0.39530 | 0.85400 | 0.0370* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0259 (3) | 0.0181 (3) | 0.0254 (4) | 0.0010 (3) | 0.0143 (3) | 0.0023 (3) |
C1 | 0.0195 (3) | 0.0180 (4) | 0.0158 (3) | −0.0010 (3) | 0.0064 (3) | −0.0002 (3) |
C2 | 0.0232 (3) | 0.0206 (4) | 0.0181 (3) | −0.0012 (3) | 0.0109 (3) | 0.0008 (3) |
C3 | 0.0229 (3) | 0.0208 (4) | 0.0188 (4) | −0.0002 (3) | 0.0112 (3) | −0.0007 (3) |
C4 | 0.0211 (3) | 0.0185 (4) | 0.0169 (3) | −0.0010 (3) | 0.0080 (3) | −0.0008 (3) |
C5 | 0.0242 (4) | 0.0194 (4) | 0.0198 (4) | −0.0015 (3) | 0.0121 (3) | 0.0004 (3) |
C6 | 0.0226 (3) | 0.0196 (4) | 0.0197 (4) | 0.0001 (3) | 0.0114 (3) | 0.0000 (3) |
C7 | 0.0219 (3) | 0.0189 (4) | 0.0159 (3) | −0.0004 (3) | 0.0092 (3) | −0.0006 (3) |
C8 | 0.0210 (3) | 0.0224 (4) | 0.0186 (4) | −0.0012 (3) | 0.0079 (3) | −0.0019 (3) |
C9 | 0.0204 (3) | 0.0245 (4) | 0.0186 (3) | 0.0019 (3) | 0.0070 (3) | −0.0001 (3) |
C10 | 0.0218 (3) | 0.0210 (4) | 0.0155 (3) | 0.0023 (3) | 0.0077 (3) | 0.0008 (3) |
C11 | 0.0244 (4) | 0.0226 (4) | 0.0194 (4) | 0.0045 (3) | 0.0085 (3) | 0.0018 (3) |
C12 | 0.0293 (4) | 0.0192 (4) | 0.0201 (4) | 0.0043 (3) | 0.0107 (3) | 0.0016 (3) |
C13 | 0.0271 (4) | 0.0188 (4) | 0.0168 (3) | 0.0007 (3) | 0.0092 (3) | 0.0004 (3) |
C14 | 0.0319 (4) | 0.0184 (4) | 0.0239 (4) | −0.0022 (3) | 0.0103 (3) | −0.0006 (3) |
C15 | 0.0300 (4) | 0.0219 (4) | 0.0251 (4) | −0.0054 (3) | 0.0079 (3) | −0.0012 (3) |
C16 | 0.0239 (4) | 0.0233 (4) | 0.0215 (4) | −0.0025 (3) | 0.0067 (3) | 0.0001 (3) |
C17 | 0.0224 (4) | 0.0201 (4) | 0.0157 (3) | −0.0006 (3) | 0.0076 (3) | 0.0005 (3) |
C18 | 0.0225 (3) | 0.0185 (4) | 0.0145 (3) | 0.0001 (3) | 0.0078 (3) | 0.0003 (3) |
C19 | 0.0216 (3) | 0.0180 (4) | 0.0139 (3) | 0.0011 (3) | 0.0079 (3) | 0.0002 (3) |
C20 | 0.0213 (3) | 0.0183 (4) | 0.0143 (3) | 0.0009 (3) | 0.0082 (3) | 0.0005 (3) |
C21 | 0.0219 (3) | 0.0189 (4) | 0.0170 (3) | 0.0023 (3) | 0.0077 (3) | 0.0014 (3) |
C22 | 0.0210 (3) | 0.0218 (4) | 0.0177 (3) | 0.0016 (3) | 0.0070 (3) | 0.0014 (3) |
C23 | 0.0285 (4) | 0.0222 (4) | 0.0263 (4) | 0.0006 (3) | 0.0138 (3) | 0.0056 (3) |
C24 | 0.0290 (4) | 0.0222 (4) | 0.0269 (4) | 0.0045 (3) | 0.0148 (3) | 0.0023 (3) |
N1—C1 | 1.3826 (12) | C17—C22 | 1.4318 (14) |
N1—C23 | 1.4445 (13) | C18—C19 | 1.4298 (13) |
N1—C24 | 1.4433 (14) | C19—C20 | 1.4244 (14) |
C1—C2 | 1.4098 (14) | C20—C21 | 1.4399 (14) |
C1—C6 | 1.4099 (14) | C21—C22 | 1.3573 (14) |
C2—C3 | 1.3878 (14) | C2—H2 | 0.9500 |
C3—C4 | 1.3967 (14) | C3—H3 | 0.9500 |
C4—C5 | 1.3986 (14) | C5—H5 | 0.9500 |
C4—C7 | 1.4850 (14) | C6—H6 | 0.9500 |
C5—C6 | 1.3862 (14) | C8—H8 | 0.9500 |
C7—C8 | 1.3990 (14) | C9—H9 | 0.9500 |
C7—C20 | 1.4164 (14) | C11—H11 | 0.9500 |
C8—C9 | 1.3845 (14) | C12—H12 | 0.9500 |
C9—C10 | 1.3995 (14) | C14—H14 | 0.9500 |
C10—C11 | 1.4352 (14) | C15—H15 | 0.9500 |
C10—C19 | 1.4246 (13) | C16—H16 | 0.9500 |
C11—C12 | 1.3565 (14) | C21—H21 | 0.9500 |
C12—C13 | 1.4375 (15) | C22—H22 | 0.9500 |
C13—C14 | 1.4020 (14) | C23—H52A | 0.9800 |
C13—C18 | 1.4253 (14) | C23—H52B | 0.9800 |
C14—C15 | 1.3897 (16) | C23—H52C | 0.9800 |
C15—C16 | 1.3873 (14) | C24—H52D | 0.9800 |
C16—C17 | 1.4020 (14) | C24—H52E | 0.9800 |
C17—C18 | 1.4241 (14) | C24—H52F | 0.9800 |
C1—N1—C23 | 120.30 (8) | C20—C21—C22 | 121.72 (9) |
C1—N1—C24 | 120.01 (8) | C17—C22—C21 | 121.26 (9) |
C23—N1—C24 | 119.50 (7) | C1—C2—H2 | 120.00 |
N1—C1—C2 | 121.37 (8) | C3—C2—H2 | 120.00 |
N1—C1—C6 | 120.99 (9) | C2—C3—H3 | 119.00 |
C2—C1—C6 | 117.64 (9) | C4—C3—H3 | 119.00 |
C1—C2—C3 | 120.61 (9) | C4—C5—H5 | 119.00 |
C2—C3—C4 | 121.86 (9) | C6—C5—H5 | 119.00 |
C3—C4—C5 | 117.34 (9) | C1—C6—H6 | 120.00 |
C3—C4—C7 | 120.70 (8) | C5—C6—H6 | 120.00 |
C5—C4—C7 | 121.95 (8) | C7—C8—H8 | 119.00 |
C4—C5—C6 | 121.79 (9) | C9—C8—H8 | 119.00 |
C1—C6—C5 | 120.70 (9) | C8—C9—H9 | 120.00 |
C4—C7—C8 | 120.05 (8) | C10—C9—H9 | 120.00 |
C4—C7—C20 | 121.04 (8) | C10—C11—H11 | 119.00 |
C8—C7—C20 | 118.88 (9) | C12—C11—H11 | 119.00 |
C7—C8—C9 | 121.98 (9) | C11—C12—H12 | 120.00 |
C8—C9—C10 | 120.67 (9) | C13—C12—H12 | 120.00 |
C9—C10—C11 | 122.31 (9) | C13—C14—H14 | 120.00 |
C9—C10—C19 | 118.72 (9) | C15—C14—H14 | 120.00 |
C11—C10—C19 | 118.96 (8) | C14—C15—H15 | 120.00 |
C10—C11—C12 | 121.59 (9) | C16—C15—H15 | 120.00 |
C11—C12—C13 | 120.98 (9) | C15—C16—H16 | 120.00 |
C12—C13—C14 | 122.18 (9) | C17—C16—H16 | 120.00 |
C12—C13—C18 | 118.76 (8) | C20—C21—H21 | 119.00 |
C14—C13—C18 | 119.06 (9) | C22—C21—H21 | 119.00 |
C13—C14—C15 | 120.62 (9) | C17—C22—H22 | 119.00 |
C14—C15—C16 | 120.79 (9) | C21—C22—H22 | 119.00 |
C15—C16—C17 | 120.65 (9) | N1—C23—H52A | 109.00 |
C16—C17—C18 | 119.11 (9) | N1—C23—H52B | 110.00 |
C16—C17—C22 | 122.15 (9) | N1—C23—H52C | 109.00 |
C18—C17—C22 | 118.74 (8) | H52A—C23—H52B | 109.00 |
C13—C18—C17 | 119.77 (8) | H52A—C23—H52C | 109.00 |
C13—C18—C19 | 120.24 (8) | H52B—C23—H52C | 109.00 |
C17—C18—C19 | 119.98 (8) | N1—C24—H52D | 109.00 |
C10—C19—C18 | 119.46 (8) | N1—C24—H52E | 109.00 |
C10—C19—C20 | 120.36 (8) | N1—C24—H52F | 109.00 |
C18—C19—C20 | 120.17 (8) | H52D—C24—H52E | 109.00 |
C7—C20—C19 | 119.37 (8) | H52D—C24—H52F | 109.00 |
C7—C20—C21 | 122.44 (9) | H52E—C24—H52F | 109.00 |
C19—C20—C21 | 118.14 (8) | ||
C23—N1—C1—C2 | −4.74 (13) | C11—C10—C19—C20 | 179.94 (8) |
C23—N1—C1—C6 | 175.91 (8) | C10—C11—C12—C13 | 0.52 (14) |
C24—N1—C1—C2 | −179.66 (8) | C11—C12—C13—C14 | 177.63 (9) |
C24—N1—C1—C6 | 0.99 (13) | C11—C12—C13—C18 | −1.31 (14) |
N1—C1—C2—C3 | −177.93 (8) | C12—C13—C14—C15 | −179.17 (9) |
C6—C1—C2—C3 | 1.44 (13) | C18—C13—C14—C15 | −0.23 (14) |
N1—C1—C6—C5 | 177.17 (9) | C12—C13—C18—C17 | 179.69 (8) |
C2—C1—C6—C5 | −2.20 (13) | C12—C13—C18—C19 | 0.73 (13) |
C1—C2—C3—C4 | 0.79 (14) | C14—C13—C18—C17 | 0.72 (13) |
C2—C3—C4—C5 | −2.22 (13) | C14—C13—C18—C19 | −178.25 (9) |
C2—C3—C4—C7 | 176.62 (8) | C13—C14—C15—C16 | −0.61 (15) |
C3—C4—C5—C6 | 1.44 (13) | C14—C15—C16—C17 | 0.95 (15) |
C7—C4—C5—C6 | −177.39 (8) | C15—C16—C17—C18 | −0.44 (13) |
C3—C4—C7—C8 | 62.00 (11) | C15—C16—C17—C22 | 178.41 (9) |
C3—C4—C7—C20 | −115.98 (10) | C16—C17—C18—C13 | −0.39 (13) |
C5—C4—C7—C8 | −119.22 (10) | C16—C17—C18—C19 | 178.58 (8) |
C5—C4—C7—C20 | 62.80 (11) | C22—C17—C18—C13 | −179.28 (8) |
C4—C5—C6—C1 | 0.77 (14) | C22—C17—C18—C19 | −0.31 (12) |
C4—C7—C8—C9 | −179.10 (8) | C16—C17—C22—C21 | −178.57 (9) |
C20—C7—C8—C9 | −1.07 (13) | C18—C17—C22—C21 | 0.30 (13) |
C4—C7—C20—C19 | 178.40 (8) | C13—C18—C19—C10 | 0.63 (12) |
C4—C7—C20—C21 | 0.82 (13) | C13—C18—C19—C20 | 179.27 (8) |
C8—C7—C20—C19 | 0.39 (12) | C17—C18—C19—C10 | −178.34 (8) |
C8—C7—C20—C21 | −177.19 (8) | C17—C18—C19—C20 | 0.30 (12) |
C7—C8—C9—C10 | 0.64 (14) | C10—C19—C20—C7 | 0.69 (12) |
C8—C9—C10—C11 | 179.36 (9) | C10—C19—C20—C21 | 178.38 (8) |
C8—C9—C10—C19 | 0.47 (13) | C18—C19—C20—C7 | −177.94 (8) |
C9—C10—C11—C12 | −178.03 (9) | C18—C19—C20—C21 | −0.26 (12) |
C19—C10—C11—C12 | 0.86 (13) | C7—C20—C21—C22 | 177.84 (9) |
C9—C10—C19—C18 | 177.52 (8) | C19—C20—C21—C22 | 0.24 (13) |
C9—C10—C19—C20 | −1.12 (12) | C20—C21—C22—C17 | −0.26 (14) |
C11—C10—C19—C18 | −1.41 (12) |
Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C1–C6, C7–C10/C19/C20, C10–C13/C18/C19, C13–C18 and C17–C22 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg2i | 0.95 | 2.93 | 3.6043 (15) | 129 |
C6—H6···Cg5ii | 0.95 | 2.90 | 3.6495 (15) | 137 |
C22—H22···Cg1iii | 0.95 | 2.68 | 3.5499 (15) | 152 |
C23—H52A···Cg3i | 0.98 | 2.74 | 3.5994 (15) | 147 |
C24—H52E···Cg4ii | 0.98 | 2.77 | 3.5284 (15) | 135 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x−1, −y+1/2, z−1/2. |
Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C1–C6, C7–C10/C19/C20, C10–C13/C18/C19, C13–C18 and C17–C22 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Cg2i | 0.95 | 2.93 | 3.6043 (15) | 129 |
C6—H6···Cg5ii | 0.95 | 2.90 | 3.6495 (15) | 137 |
C22—H22···Cg1iii | 0.95 | 2.68 | 3.5499 (15) | 152 |
C23—H52A···Cg3i | 0.98 | 2.74 | 3.5994 (15) | 147 |
C24—H52E···Cg4ii | 0.98 | 2.77 | 3.5284 (15) | 135 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) x−1, −y+1/2, z−1/2. |
ST thanks the DFG, SFB 755 and SFB 1073 for financial support. STV thanks G. Busse and L. Busse for technical help.
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Electron donor acceptor molecules play an important role in the understanding of charge transfer processes. In the past decades, in order to gain more insight into electron transfer processes, extensive studies have been carried out on the optical behavior of systems consisting of donor acceptor groups linked by different bridges (Wasielewski, 1992; Willemse et al., 2000). These molecules are also ideal systems for studying the solvation dynamics and also for the demonstration of non-linear optical properties. Pyrene-N,N-dimethylaniline (PyDMA), is a compound in which the electron donor N,N-dimethylaniline (DMA) is covalently linked to the electron acceptor pyrene. Due to the lack of an extended bridge between the donor and acceptor in PyDMA, the physical characteristics of these groups strongly influence the electron transfer mechanism. This leads to a very unusual absorption and emission spectra in the optical regime and because of this PyDMA is considered to be a molecular diode where electron donor and electron acceptor moieties are twisted against each other modulating the electron charge transfer processes.
The title compound, Fig. 1, is a pyrene derivative. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to those reported for a similar structure, N,N-Diphenyl-4-(pyren-1-yl)aniline (Wang et al., 2010). The dimethylamine group and the benzene ring are almost coplanar (dihedral angle = 2.81 (9) °) and their mean plane makes a dihedral angle of 64.12 (2) ° with the pyrene ring system [r.m.s.d. = 0.031 (1) Å].
In the crystal, packing is stabilized by C—H···π interactions (Table 1). The interaction C23—H52A···Cg3i (see Table 1; Cg3 is the centroid of the C10-C13/C18/C19 ring) connects neighbouring molecules into columns along the c-axis (Fig. 2).