Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803005749/fl6021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803005749/fl6021Isup2.hkl |
CCDC reference: 209969
In an attempt to synthesize monoalkylated polyazaarenes, we heated a mixture of chloroaldehyde with 3-naphthylamine to get dihydrodibenzacridine, which on dehydrogenation with Pd—C (10%) in p-cymene produced dihydrodibenz[a,h]acridine (Halder et al., 1989). The direct alkylation of dibenz[a,h]acridine with three equivalents of n-butyllithium produced the title compound in 70% yield (see Scheme). Single crystals were obtained by slow evaporation from a chloroform–petroleum ether solution.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C25H21N | F(000) = 1424 |
Mr = 335.43 | Dx = 1.215 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 10111 reflections |
a = 19.5507 (11) Å | θ = 1.4–28.4° |
b = 12.7195 (7) Å | µ = 0.07 mm−1 |
c = 14.7732 (8) Å | T = 298 K |
β = 93.322 (1)° | Block, yellow |
V = 3667.6 (4) Å3 | 0.50 × 0.25 × 0.25 mm |
Z = 8 |
Bruker SMART 1K CCD area-detector diffractometer | 4539 independent reflections |
Radiation source: fine-focus sealed tube | 2208 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −25→26 |
Tmin = 0.966, Tmax = 0.983 | k = −14→16 |
12785 measured reflections | l = −17→19 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0845P)2] where P = (Fo2 + 2Fc2)/3 |
4539 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C25H21N | V = 3667.6 (4) Å3 |
Mr = 335.43 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 19.5507 (11) Å | µ = 0.07 mm−1 |
b = 12.7195 (7) Å | T = 298 K |
c = 14.7732 (8) Å | 0.50 × 0.25 × 0.25 mm |
β = 93.322 (1)° |
Bruker SMART 1K CCD area-detector diffractometer | 4539 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2208 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.983 | Rint = 0.035 |
12785 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.17 e Å−3 |
4539 reflections | Δρmin = −0.16 e Å−3 |
236 parameters |
Experimental. Data was collected using a Siemens SMART CCD based diffractometer operating at room temperature. Data was measured using omega scans of 0.3 degrees per frame for 60 s. A total of 1271 frames were collected. The first 50 frames were recollected at the end of each set of frames. |
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 | ||
N1 | 0.20712 (7) | 0.94371 (11) | 0.12336 (9) | 0.0606 (4) | |
C1 | 0.24753 (8) | 0.97813 (12) | 0.05954 (10) | 0.0579 (4) | |
C2 | 0.30655 (8) | 0.92382 (12) | 0.03031 (10) | 0.0548 (4) | |
C3 | 0.31644 (8) | 0.82032 (12) | 0.06486 (10) | 0.0553 (4) | |
C4 | 0.27295 (8) | 0.78358 (12) | 0.13108 (10) | 0.0562 (4) | |
C5 | 0.21998 (8) | 0.84883 (12) | 0.16050 (10) | 0.0560 (4) | |
C6 | 0.17452 (9) | 0.81306 (13) | 0.22835 (11) | 0.0619 (4) | |
C7 | 0.18200 (9) | 0.71022 (14) | 0.26268 (11) | 0.0667 (5) | |
C8 | 0.23510 (10) | 0.64576 (14) | 0.23078 (12) | 0.0728 (5) | |
H8 | 0.2400 | 0.5777 | 0.2532 | 0.087* | |
C9 | 0.27818 (10) | 0.67897 (13) | 0.16997 (11) | 0.0670 (5) | |
H9 | 0.3124 | 0.6339 | 0.1521 | 0.080* | |
C10 | 0.13686 (11) | 0.67508 (17) | 0.32735 (13) | 0.0850 (6) | |
H10 | 0.1411 | 0.6069 | 0.3498 | 0.102* | |
C11 | 0.08733 (12) | 0.7390 (2) | 0.35754 (15) | 0.0969 (7) | |
H11 | 0.0584 | 0.7148 | 0.4008 | 0.116* | |
C12 | 0.08009 (11) | 0.8407 (2) | 0.32361 (15) | 0.0961 (7) | |
H12 | 0.0460 | 0.8842 | 0.3440 | 0.115* | |
C13 | 0.12285 (9) | 0.87702 (17) | 0.26036 (13) | 0.0786 (5) | |
H13 | 0.1175 | 0.9452 | 0.2384 | 0.094* | |
C14 | 0.34738 (8) | 0.97676 (12) | −0.03665 (10) | 0.0586 (4) | |
C15 | 0.32027 (9) | 1.06796 (13) | −0.08092 (11) | 0.0632 (5) | |
C16 | 0.25865 (10) | 1.11449 (14) | −0.05257 (12) | 0.0726 (5) | |
H16 | 0.2411 | 1.1737 | −0.0826 | 0.087* | |
C17 | 0.22571 (9) | 1.07480 (14) | 0.01609 (12) | 0.0705 (5) | |
H17 | 0.1879 | 1.1102 | 0.0364 | 0.085* | |
C18 | 0.35498 (11) | 1.11460 (16) | −0.15061 (13) | 0.0789 (6) | |
H18 | 0.3357 | 1.1727 | −0.1805 | 0.095* | |
C19 | 0.41616 (12) | 1.07725 (18) | −0.17583 (14) | 0.0913 (6) | |
H19 | 0.4375 | 1.1070 | −0.2243 | 0.110* | |
C20 | 0.44616 (11) | 0.99406 (18) | −0.12793 (15) | 0.0924 (6) | |
H20 | 0.4893 | 0.9705 | −0.1421 | 0.111* | |
C21 | 0.41315 (9) | 0.94612 (15) | −0.05999 (13) | 0.0759 (5) | |
H21 | 0.4350 | 0.8914 | −0.0282 | 0.091* | |
C22 | 0.36725 (9) | 0.74302 (13) | 0.02976 (10) | 0.0645 (5) | |
H22 | 0.3795 | 0.7660 | −0.0298 | 0.077* | |
H22B | 0.3450 | 0.6751 | 0.0225 | 0.077* | |
C23 | 0.43282 (9) | 0.72905 (14) | 0.08958 (12) | 0.0711 (5) | |
H23 | 0.4211 | 0.7182 | 0.1518 | 0.085* | |
H23B | 0.4600 | 0.7927 | 0.0876 | 0.085* | |
C24 | 0.47531 (11) | 0.63607 (17) | 0.05943 (14) | 0.0941 (7) | |
H24 | 0.4473 | 0.5731 | 0.0600 | 0.113* | |
H24B | 0.4872 | 0.6479 | −0.0026 | 0.113* | |
C25 | 0.53920 (12) | 0.6175 (2) | 0.1164 (2) | 0.1271 (9) | |
H25 | 0.5611 | 0.5547 | 0.0965 | 0.191* | |
H25B | 0.5283 | 0.6096 | 0.1786 | 0.191* | |
H25C | 0.5696 | 0.6762 | 0.1110 | 0.191* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0662 (8) | 0.0527 (8) | 0.0618 (8) | 0.0036 (7) | −0.0049 (7) | 0.0032 (6) |
C1 | 0.0640 (10) | 0.0484 (9) | 0.0598 (10) | 0.0018 (8) | −0.0100 (8) | 0.0010 (7) |
C2 | 0.0638 (10) | 0.0491 (9) | 0.0497 (9) | 0.0007 (8) | −0.0116 (8) | −0.0021 (7) |
C3 | 0.0650 (10) | 0.0490 (9) | 0.0499 (9) | 0.0048 (8) | −0.0126 (8) | −0.0051 (7) |
C4 | 0.0696 (10) | 0.0480 (9) | 0.0491 (9) | 0.0006 (8) | −0.0126 (8) | −0.0014 (7) |
C5 | 0.0610 (9) | 0.0518 (9) | 0.0535 (9) | 0.0001 (8) | −0.0123 (8) | −0.0021 (7) |
C6 | 0.0659 (10) | 0.0620 (11) | 0.0565 (10) | −0.0061 (9) | −0.0074 (8) | 0.0011 (8) |
C7 | 0.0769 (12) | 0.0631 (11) | 0.0583 (10) | −0.0089 (9) | −0.0108 (9) | 0.0019 (8) |
C8 | 0.1029 (14) | 0.0507 (10) | 0.0635 (11) | −0.0050 (10) | −0.0066 (11) | 0.0079 (8) |
C9 | 0.0894 (13) | 0.0511 (10) | 0.0592 (10) | 0.0084 (9) | −0.0069 (10) | 0.0003 (8) |
C10 | 0.0969 (15) | 0.0785 (14) | 0.0788 (13) | −0.0207 (12) | −0.0031 (12) | 0.0151 (11) |
C11 | 0.0874 (15) | 0.1040 (19) | 0.1008 (16) | −0.0163 (14) | 0.0175 (13) | 0.0124 (14) |
C12 | 0.0787 (13) | 0.1072 (19) | 0.1037 (16) | 0.0038 (13) | 0.0173 (13) | 0.0124 (14) |
C13 | 0.0721 (12) | 0.0795 (13) | 0.0839 (13) | 0.0068 (11) | 0.0034 (11) | 0.0105 (10) |
C14 | 0.0645 (10) | 0.0546 (10) | 0.0554 (9) | −0.0017 (8) | −0.0092 (8) | −0.0021 (8) |
C15 | 0.0723 (11) | 0.0556 (10) | 0.0600 (10) | −0.0050 (9) | −0.0098 (9) | 0.0057 (8) |
C16 | 0.0825 (12) | 0.0558 (11) | 0.0776 (12) | 0.0090 (9) | −0.0117 (10) | 0.0139 (9) |
C17 | 0.0742 (11) | 0.0572 (11) | 0.0794 (12) | 0.0117 (9) | −0.0025 (10) | 0.0099 (9) |
C18 | 0.0880 (14) | 0.0700 (12) | 0.0772 (13) | −0.0050 (11) | −0.0092 (11) | 0.0170 (10) |
C19 | 0.0969 (16) | 0.0930 (16) | 0.0848 (14) | −0.0069 (13) | 0.0113 (12) | 0.0254 (12) |
C20 | 0.0811 (13) | 0.0952 (16) | 0.1022 (15) | 0.0012 (12) | 0.0165 (12) | 0.0165 (13) |
C21 | 0.0754 (12) | 0.0724 (12) | 0.0796 (12) | 0.0033 (10) | 0.0017 (10) | 0.0121 (10) |
C22 | 0.0826 (11) | 0.0506 (9) | 0.0594 (10) | 0.0057 (9) | −0.0039 (9) | −0.0047 (8) |
C23 | 0.0761 (12) | 0.0660 (11) | 0.0705 (11) | 0.0144 (9) | −0.0015 (9) | 0.0022 (9) |
C24 | 0.0941 (15) | 0.0865 (15) | 0.1030 (16) | 0.0291 (12) | 0.0155 (13) | −0.0044 (12) |
C25 | 0.0955 (17) | 0.114 (2) | 0.172 (2) | 0.0417 (15) | 0.0036 (17) | −0.0025 (19) |
N1—C1 | 1.338 (2) | C14—C15 | 1.419 (2) |
N1—C5 | 1.3433 (19) | C15—C18 | 1.398 (2) |
C1—C2 | 1.433 (2) | C15—C16 | 1.427 (2) |
C1—C17 | 1.440 (2) | C16—C17 | 1.332 (2) |
C2—C3 | 1.421 (2) | C16—H16 | 0.9300 |
C2—C14 | 1.470 (2) | C17—H17 | 0.9300 |
C3—C4 | 1.412 (2) | C18—C19 | 1.359 (3) |
C3—C22 | 1.511 (2) | C18—H18 | 0.9300 |
C4—C5 | 1.415 (2) | C19—C20 | 1.384 (3) |
C4—C9 | 1.451 (2) | C19—H19 | 0.9300 |
C5—C6 | 1.451 (2) | C20—C21 | 1.368 (3) |
C6—C13 | 1.400 (2) | C20—H20 | 0.9300 |
C6—C7 | 1.407 (2) | C21—H21 | 0.9300 |
C7—C10 | 1.410 (3) | C22—C23 | 1.525 (2) |
C7—C8 | 1.424 (3) | C22—H22 | 0.9700 |
C8—C9 | 1.335 (2) | C22—H22B | 0.9700 |
C8—H8 | 0.9300 | C23—C24 | 1.526 (3) |
C9—H9 | 0.9300 | C23—H23 | 0.9700 |
C10—C11 | 1.359 (3) | C23—H23B | 0.9700 |
C10—H10 | 0.9300 | C24—C25 | 1.484 (3) |
C11—C12 | 1.391 (3) | C24—H24 | 0.9700 |
C11—H11 | 0.9300 | C24—H24B | 0.9700 |
C12—C13 | 1.370 (3) | C25—H25 | 0.9600 |
C12—H12 | 0.9300 | C25—H25B | 0.9600 |
C13—H13 | 0.9300 | C25—H25C | 0.9600 |
C14—C21 | 1.406 (2) | ||
C1—N1—C5 | 118.52 (14) | C18—C15—C16 | 119.64 (17) |
N1—C1—C2 | 124.98 (14) | C14—C15—C16 | 120.19 (16) |
N1—C1—C17 | 114.94 (15) | C17—C16—C15 | 121.33 (16) |
C2—C1—C17 | 120.01 (16) | C17—C16—H16 | 119.3 |
C3—C2—C1 | 115.69 (15) | C15—C16—H16 | 119.3 |
C3—C2—C14 | 126.74 (15) | C16—C17—C1 | 121.29 (17) |
C1—C2—C14 | 117.40 (14) | C16—C17—H17 | 119.4 |
C4—C3—C2 | 118.71 (14) | C1—C17—H17 | 119.4 |
C4—C3—C22 | 117.17 (14) | C19—C18—C15 | 121.74 (18) |
C2—C3—C22 | 123.93 (15) | C19—C18—H18 | 119.1 |
C3—C4—C5 | 119.96 (14) | C15—C18—H18 | 119.1 |
C3—C4—C9 | 123.12 (15) | C18—C19—C20 | 118.7 (2) |
C5—C4—C9 | 116.90 (16) | C18—C19—H19 | 120.6 |
N1—C5—C4 | 121.63 (15) | C20—C19—H19 | 120.6 |
N1—C5—C6 | 117.15 (15) | C21—C20—C19 | 120.8 (2) |
C4—C5—C6 | 121.12 (15) | C21—C20—H20 | 119.6 |
C13—C6—C7 | 118.69 (17) | C19—C20—H20 | 119.6 |
C13—C6—C5 | 122.26 (16) | C20—C21—C14 | 122.25 (18) |
C7—C6—C5 | 119.04 (16) | C20—C21—H21 | 118.9 |
C6—C7—C10 | 118.85 (18) | C14—C21—H21 | 118.9 |
C6—C7—C8 | 118.58 (17) | C3—C22—C23 | 115.11 (13) |
C10—C7—C8 | 122.57 (18) | C3—C22—H22 | 108.5 |
C9—C8—C7 | 122.74 (17) | C23—C22—H22 | 108.5 |
C9—C8—H8 | 118.6 | C3—C22—H22B | 108.5 |
C7—C8—H8 | 118.6 | C23—C22—H22B | 108.5 |
C8—C9—C4 | 121.60 (17) | H22—C22—H22B | 107.5 |
C8—C9—H9 | 119.2 | C22—C23—C24 | 112.00 (15) |
C4—C9—H9 | 119.2 | C22—C23—H23 | 109.2 |
C11—C10—C7 | 121.2 (2) | C24—C23—H23 | 109.2 |
C11—C10—H10 | 119.4 | C22—C23—H23B | 109.2 |
C7—C10—H10 | 119.4 | C24—C23—H23B | 109.2 |
C10—C11—C12 | 119.8 (2) | H23—C23—H23B | 107.9 |
C10—C11—H11 | 120.1 | C25—C24—C23 | 114.34 (18) |
C12—C11—H11 | 120.1 | C25—C24—H24 | 108.7 |
C13—C12—C11 | 120.4 (2) | C23—C24—H24 | 108.7 |
C13—C12—H12 | 119.8 | C25—C24—H24B | 108.7 |
C11—C12—H12 | 119.8 | C23—C24—H24B | 108.7 |
C12—C13—C6 | 121.0 (2) | H24—C24—H24B | 107.6 |
C12—C13—H13 | 119.5 | C24—C25—H25 | 109.5 |
C6—C13—H13 | 119.5 | C24—C25—H25B | 109.5 |
C21—C14—C15 | 115.86 (16) | H25—C25—H25B | 109.5 |
C21—C14—C2 | 125.33 (15) | C24—C25—H25C | 109.5 |
C15—C14—C2 | 118.79 (15) | H25—C25—H25C | 109.5 |
C18—C15—C14 | 120.14 (17) | H25B—C25—H25C | 109.5 |
C5—N1—C1—C2 | −3.5 (2) | C5—C4—C9—C8 | −0.1 (2) |
C5—N1—C1—C17 | 173.30 (13) | C6—C7—C10—C11 | −0.9 (3) |
N1—C1—C2—C3 | 8.1 (2) | C8—C7—C10—C11 | 178.98 (18) |
C17—C1—C2—C3 | −168.54 (14) | C7—C10—C11—C12 | 0.8 (3) |
N1—C1—C2—C14 | −176.25 (13) | C10—C11—C12—C13 | −0.4 (3) |
C17—C1—C2—C14 | 7.1 (2) | C11—C12—C13—C6 | 0.1 (3) |
C1—C2—C3—C4 | −6.52 (19) | C7—C6—C13—C12 | −0.2 (3) |
C14—C2—C3—C4 | 178.33 (13) | C5—C6—C13—C12 | 179.14 (17) |
C1—C2—C3—C22 | 168.36 (13) | C3—C2—C14—C21 | −17.9 (2) |
C14—C2—C3—C22 | −6.8 (2) | C1—C2—C14—C21 | 166.99 (15) |
C2—C3—C4—C5 | 1.2 (2) | C3—C2—C14—C15 | 163.67 (14) |
C22—C3—C4—C5 | −174.05 (13) | C1—C2—C14—C15 | −11.4 (2) |
C2—C3—C4—C9 | 179.29 (14) | C21—C14—C15—C18 | 7.2 (2) |
C22—C3—C4—C9 | 4.1 (2) | C2—C14—C15—C18 | −174.30 (14) |
C1—N1—C5—C4 | −2.7 (2) | C21—C14—C15—C16 | −170.79 (16) |
C1—N1—C5—C6 | −178.96 (13) | C2—C14—C15—C16 | 7.8 (2) |
C3—C4—C5—N1 | 3.8 (2) | C18—C15—C16—C17 | −177.18 (16) |
C9—C4—C5—N1 | −174.45 (13) | C14—C15—C16—C17 | 0.8 (3) |
C3—C4—C5—C6 | 179.93 (13) | C15—C16—C17—C1 | −5.4 (3) |
C9—C4—C5—C6 | 1.7 (2) | N1—C1—C17—C16 | −175.68 (15) |
N1—C5—C6—C13 | −5.4 (2) | C2—C1—C17—C16 | 1.3 (2) |
C4—C5—C6—C13 | 178.29 (15) | C14—C15—C18—C19 | −2.4 (3) |
N1—C5—C6—C7 | 173.96 (13) | C16—C15—C18—C19 | 175.55 (18) |
C4—C5—C6—C7 | −2.3 (2) | C15—C18—C19—C20 | −3.3 (3) |
C13—C6—C7—C10 | 0.6 (2) | C18—C19—C20—C21 | 3.8 (3) |
C5—C6—C7—C10 | −178.81 (14) | C19—C20—C21—C14 | 1.3 (3) |
C13—C6—C7—C8 | −179.28 (15) | C15—C14—C21—C20 | −6.7 (3) |
C5—C6—C7—C8 | 1.3 (2) | C2—C14—C21—C20 | 174.86 (16) |
C6—C7—C8—C9 | 0.3 (2) | C4—C3—C22—C23 | −81.85 (18) |
C10—C7—C8—C9 | −179.59 (16) | C2—C3—C22—C23 | 103.20 (18) |
C7—C8—C9—C4 | −0.9 (3) | C3—C22—C23—C24 | 169.42 (16) |
C3—C4—C9—C8 | −178.25 (15) | C22—C23—C24—C25 | −178.93 (18) |
Experimental details
Crystal data | |
Chemical formula | C25H21N |
Mr | 335.43 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 19.5507 (11), 12.7195 (7), 14.7732 (8) |
β (°) | 93.322 (1) |
V (Å3) | 3667.6 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.50 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART 1K CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.966, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12785, 4539, 2208 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.167, 0.99 |
No. of reflections | 4539 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
C2—C3 | 1.421 (2) | C3—C4 | 1.412 (2) |
C2—C14 | 1.470 (2) | C4—C9 | 1.451 (2) |
N1—C1—C2 | 124.98 (14) | C21—C14—C15 | 115.86 (16) |
C3—C2—C1 | 115.69 (15) | C21—C14—C2 | 125.33 (15) |
C3—C2—C14 | 126.74 (15) | C3—C22—C23 | 115.11 (13) |
C5—N1—C1—C2 | −3.5 (2) | C3—C2—C14—C15 | 163.67 (14) |
C5—N1—C1—C17 | 173.30 (13) | C1—C2—C14—C15 | −11.4 (2) |
N1—C1—C2—C3 | 8.1 (2) | C4—C3—C22—C23 | −81.85 (18) |
C17—C1—C2—C3 | −168.54 (14) | C2—C3—C22—C23 | 103.20 (18) |
C1—C2—C3—C22 | 168.36 (13) | C3—C22—C23—C24 | 169.42 (16) |
C3—C2—C14—C21 | −17.9 (2) | C22—C23—C24—C25 | −178.93 (18) |
C1—C2—C14—C21 | 166.99 (15) |
Use of alkylated acridine derivatives in molecular recognitions have made enormous strides in recent years (Pan et al., 2000). Regioselective alkylation of polycyclic benz and dibenz acridines not only improves the solubility of these compounds in common organic solvents (Ray et al. 1996), but also provides a simple path for the synthesis of alkylated molecular hosts (Halder et al., 1997).
Molecule (I) is composed of five (A, B, C, D and E) fused six-membered aromatic rings with one n-butyl chain at the para position of the central ring (Fig. 1). The conformation adopted by (I) in the solid state is affected by the presence of the alkyl chain at C3 (Fig. 2). C—C distances in the environment of the alkyl chain (C2—C3, C3—C4 and C4—C9) are rather similar to those found in monoclinic dibenz[a,h]anthracene (Robertson & White, 1956). On the other hand, the C2—C14 distance [1.470 (2) Å] is 0.08 Å larger than equivalent distance in dibenz[a,h]anthracene. All ring angles are reasonably close to ideal geometry, the presence of the alkyl chain increases the C3—C2—C14 angle [to 126.74 (15)°].
Rings A and B are reasonably planar, with mean deviations from planarity of 0.0024 and 0.0075 Å, respectively. On the other hand, rings C, D and E are less planar, the corresponding mean deviations are 0.0283, 0.0396 and 0.0278 Å, respectively, the main deviation from planarity taking place at the D ring. These values and the C1—C2—C3—C4 and C1—C2—C14—C15 torsion angles (Table 1) reflect the distortion of the molecule in order to minimize the steric interaction between ring E and the alkyl chain. As expected on the basis of basic chemical grounds and obtained using molecular mechanics calculations (GAUSSIAN98 suite of programs, UFF force field; Frisch et al., 1998), the parent compound without the alkyl chain should be planar, whereas in this case the dihedral angle between rings A and E is 19.67 (10)°. The value of the C22—C23—C24—C25 torsion angle [−178.93 (18)°] implies a trans conformation for the alkyl chain. The steric interaction between the n-butyl substituent and the E ring moves the C3—C22—C23—C24 torsion angle to 169.42 (16)°.
Relevant changes respect to monoclinic dibenz[a,h]anthracene crystal take place. The presence of the alkyl chain provokes the change of symmetry space group (H—M) from P21 to C2/c, which implies modifications at β cell angle [93.3220 (10) versus 103.5°], cell lengths a [19.5507 (11) versus 6.59 Å] and b [12.7195 (7) versus 7.84 Å], and the number of cell formula units Z increases from 2 to 8. Within the three-dimensional network, it is noticeable that the alkyl chain of the one molecule is directed towards the N atom of the next molecule in the same layer (Fig. 3), thus making the packing more effective.