The crystal structure of 9-(
tert-butylamino)acridine, C
17H
18N
2, is composed of molecules of the amino tautomeric form. The acridine moiety is slightly folded along the C
N line passing through opposite atoms of the central ring, and the orientation of the
tert-butylamino group makes the conjugation between the lone pair of the N atom and the acridine π-system almost negligible. An intermolecular hydrogen bond, involving the exocyclic NH group as donor and the endocyclic N atom as acceptor, links the molecules into infinite chains stretching along the
b axis of the crystal.
Supporting information
CCDC reference: 183815
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.129
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies
outside the range 0.99 <> 1.01
Calculated value of mu = 0.072
Value of mu given = 0.070
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: KM-4 Software (Kuma Diffraction, 1989); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
N-(1,1-dimethylethyl)-9-acridinamine
top
Crystal data top
C17H18N2 | Dx = 1.214 Mg m−3 |
Mr = 250.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 50 reflections |
a = 7.623 (3) Å | θ = 1.4–25.5° |
b = 12.762 (4) Å | µ = 0.07 mm−1 |
c = 28.155 (7) Å | T = 293 K |
V = 2739.1 (15) Å3 | Needle, yellow |
Z = 8 | 0.6 × 0.4 × 0.3 mm |
F(000) = 1072 | |
Data collection top
Kuma KM-4 diffractometer | Rint = 0.100 |
Radiation source: fine-focus sealed tube | θmax = 25.6°, θmin = 1.4° |
Graphite monochromator | h = −9→9 |
θ/2θ scans | k = −14→15 |
18864 measured reflections | l = −34→34 |
2569 independent reflections | 3 standard reflections every 150 reflections |
1817 reflections with I > 2σ(I) | intensity decay: 26.8% |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.3081P] where P = (Fo2 + 2Fc2)/3 |
2569 reflections | (Δ/σ)max < 0.001 |
179 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
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. 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 >
2σ(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 | Uiso*/Ueq | |
C1 | 0.2636 (3) | 0.59316 (16) | 0.05938 (7) | 0.0432 (5) | |
H1A | 0.3184 | 0.5259 | 0.0629 | 0.052* | |
C2 | 0.1635 (3) | 0.61399 (18) | 0.02084 (8) | 0.0482 (5) | |
H2A | 0.1443 | 0.5599 | −0.0023 | 0.058* | |
C3 | 0.0860 (3) | 0.71388 (18) | 0.01513 (8) | 0.0485 (6) | |
H3A | 0.0183 | 0.7297 | −0.0127 | 0.058* | |
C4 | 0.1112 (3) | 0.78850 (16) | 0.04819 (7) | 0.0440 (5) | |
H4A | 0.0553 | 0.8555 | 0.0450 | 0.053* | |
C5 | 0.3447 (3) | 0.91217 (16) | 0.19428 (8) | 0.0448 (5) | |
H5A | 0.2931 | 0.9794 | 0.1881 | 0.054* | |
C6 | 0.4254 (3) | 0.89478 (18) | 0.23620 (8) | 0.0488 (6) | |
H6A | 0.4408 | 0.9516 | 0.2582 | 0.059* | |
C8 | 0.4821 (3) | 0.71576 (17) | 0.21573 (7) | 0.0431 (5) | |
H8A | 0.5332 | 0.6489 | 0.2229 | 0.052* | |
C7 | 0.4903 (3) | 0.79497 (17) | 0.24783 (9) | 0.0485 (5) | |
H7A | 0.5412 | 0.7806 | 0.2783 | 0.058* | |
C9 | 0.4009 (2) | 0.65204 (14) | 0.13528 (7) | 0.0340 (4) | |
N10 | 0.2346 (2) | 0.84974 (12) | 0.12045 (6) | 0.0385 (4) | |
C11 | 0.2947 (2) | 0.66932 (14) | 0.09503 (7) | 0.0341 (4) | |
C12 | 0.2147 (2) | 0.77056 (15) | 0.08933 (7) | 0.0362 (4) | |
C13 | 0.4070 (2) | 0.73128 (14) | 0.17017 (7) | 0.0347 (4) | |
C14 | 0.3267 (2) | 0.83037 (15) | 0.16030 (7) | 0.0361 (4) | |
N15 | 0.4948 (2) | 0.55810 (13) | 0.14273 (6) | 0.0376 (4) | |
H15A | 0.440 (3) | 0.5038 (18) | 0.1262 (7) | 0.052 (6)* | |
C16 | 0.6840 (3) | 0.55261 (16) | 0.12762 (8) | 0.0437 (5) | |
C17 | 0.7335 (3) | 0.43760 (18) | 0.12983 (9) | 0.0590 (7) | |
H17A | 0.6572 | 0.3981 | 0.1095 | 0.089* | |
H17B | 0.7219 | 0.4129 | 0.1619 | 0.089* | |
H17C | 0.8527 | 0.4290 | 0.1195 | 0.089* | |
C18 | 0.7085 (3) | 0.5934 (2) | 0.07745 (9) | 0.0748 (9) | |
H18A | 0.6333 | 0.5553 | 0.0562 | 0.112* | |
H18B | 0.8285 | 0.5840 | 0.0680 | 0.112* | |
H18C | 0.6793 | 0.6665 | 0.0764 | 0.112* | |
C19 | 0.8024 (3) | 0.6138 (2) | 0.16099 (10) | 0.0682 (8) | |
H19A | 0.7867 | 0.5889 | 0.1929 | 0.102* | |
H19B | 0.7729 | 0.6869 | 0.1595 | 0.102* | |
H19C | 0.9225 | 0.6044 | 0.1517 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0409 (11) | 0.0339 (11) | 0.0548 (12) | 0.0004 (9) | −0.0004 (10) | −0.0029 (9) |
C2 | 0.0480 (12) | 0.0474 (13) | 0.0493 (12) | −0.0058 (10) | −0.0017 (10) | −0.0087 (10) |
C3 | 0.0456 (12) | 0.0533 (14) | 0.0467 (13) | −0.0033 (10) | −0.0058 (10) | 0.0068 (10) |
C4 | 0.0418 (12) | 0.0389 (11) | 0.0513 (13) | 0.0032 (9) | −0.0014 (10) | 0.0066 (10) |
C5 | 0.0426 (11) | 0.0338 (11) | 0.0580 (14) | −0.0011 (9) | 0.0048 (10) | −0.0089 (9) |
C6 | 0.0480 (13) | 0.0458 (12) | 0.0527 (14) | −0.0080 (10) | 0.0035 (10) | −0.0125 (10) |
C8 | 0.0425 (12) | 0.0405 (11) | 0.0464 (12) | 0.0014 (9) | 0.0000 (9) | 0.0020 (9) |
C7 | 0.0458 (12) | 0.0535 (13) | 0.0463 (12) | −0.0063 (10) | −0.0025 (10) | −0.0027 (11) |
C9 | 0.0314 (10) | 0.0262 (9) | 0.0444 (11) | −0.0013 (8) | 0.0044 (8) | 0.0028 (8) |
N10 | 0.0376 (9) | 0.0287 (8) | 0.0490 (10) | 0.0007 (7) | 0.0010 (8) | −0.0001 (7) |
C11 | 0.0308 (10) | 0.0291 (10) | 0.0425 (11) | −0.0018 (8) | 0.0048 (8) | 0.0019 (8) |
C12 | 0.0328 (10) | 0.0324 (10) | 0.0433 (11) | −0.0002 (8) | 0.0044 (8) | 0.0046 (9) |
C13 | 0.0318 (10) | 0.0295 (9) | 0.0426 (11) | −0.0010 (8) | 0.0045 (8) | 0.0035 (8) |
C14 | 0.0319 (10) | 0.0319 (10) | 0.0445 (11) | −0.0025 (8) | 0.0065 (8) | 0.0001 (8) |
N15 | 0.0347 (9) | 0.0251 (8) | 0.0528 (10) | 0.0019 (7) | −0.0016 (8) | 0.0017 (7) |
C16 | 0.0344 (11) | 0.0371 (11) | 0.0596 (14) | 0.0049 (9) | 0.0019 (9) | 0.0014 (10) |
C17 | 0.0495 (13) | 0.0426 (13) | 0.0851 (18) | 0.0122 (11) | −0.0084 (13) | −0.0073 (12) |
C18 | 0.0494 (15) | 0.100 (2) | 0.0754 (18) | 0.0166 (15) | 0.0212 (13) | 0.0290 (16) |
C19 | 0.0389 (13) | 0.0588 (15) | 0.107 (2) | −0.0032 (11) | −0.0059 (13) | −0.0195 (15) |
Geometric parameters (Å, º) top
C1—C2 | 1.353 (3) | C9—N15 | 1.412 (2) |
C1—C11 | 1.417 (3) | N10—C12 | 1.346 (2) |
C1—H1A | 0.9600 | N10—C14 | 1.346 (3) |
C2—C3 | 1.414 (3) | C11—C12 | 1.438 (3) |
C2—H2A | 0.9599 | C13—C14 | 1.432 (3) |
C3—C4 | 1.345 (3) | N15—H15A | 0.93 (2) |
C3—H3A | 0.9601 | N15—C16 | 1.506 (3) |
C4—C12 | 1.420 (3) | C16—C17 | 1.517 (3) |
C4—H4A | 0.9600 | C16—C18 | 1.517 (3) |
C5—C6 | 1.349 (3) | C16—C19 | 1.519 (3) |
C5—C14 | 1.423 (3) | C17—H17A | 0.9600 |
C5—H5A | 0.9600 | C17—H17B | 0.9600 |
C6—C7 | 1.405 (3) | C17—H17C | 0.9600 |
C6—H6A | 0.9600 | C18—H18A | 0.9600 |
C8—C7 | 1.357 (3) | C18—H18B | 0.9600 |
C8—C13 | 1.419 (3) | C18—H18C | 0.9600 |
C8—H8A | 0.9599 | C19—H19A | 0.9600 |
C7—H7A | 0.9600 | C19—H19B | 0.9600 |
C9—C11 | 1.410 (3) | C19—H19C | 0.9600 |
C9—C13 | 1.410 (3) | | |
| | | |
C2—C1—C11 | 121.84 (19) | N10—C12—C11 | 123.64 (18) |
C2—C1—H1A | 120.3 | C4—C12—C11 | 118.14 (18) |
C11—C1—H1A | 117.8 | C9—C13—C8 | 122.88 (18) |
C1—C2—C3 | 120.3 (2) | C9—C13—C14 | 118.95 (18) |
C1—C2—H2A | 119.2 | C8—C13—C14 | 118.11 (18) |
C3—C2—H2A | 120.5 | N10—C14—C5 | 118.43 (18) |
C4—C3—C2 | 120.0 (2) | N10—C14—C13 | 123.13 (17) |
C4—C3—H3A | 119.5 | C5—C14—C13 | 118.44 (18) |
C2—C3—H3A | 120.5 | C16—N15—H15A | 104.7 (14) |
C3—C4—C12 | 122.0 (2) | N15—C16—C17 | 105.77 (17) |
C3—C4—H4A | 120.1 | N15—C16—C18 | 111.43 (18) |
C12—C4—H4A | 117.9 | C17—C16—C18 | 109.8 (2) |
C6—C5—C14 | 120.8 (2) | N15—C16—C19 | 111.76 (18) |
C6—C5—H5A | 119.4 | C17—C16—C19 | 108.94 (19) |
C14—C5—H5A | 119.7 | C18—C16—C19 | 109.0 (2) |
C5—C6—C7 | 120.9 (2) | C16—C17—H17A | 109.5 |
C5—C6—H6A | 119.7 | C16—C17—H17B | 109.5 |
C7—C6—H6A | 119.4 | H17A—C17—H17B | 109.5 |
C7—C8—C13 | 121.1 (2) | C16—C17—H17C | 109.5 |
C7—C8—H8A | 120.2 | H17A—C17—H17C | 109.5 |
C13—C8—H8A | 118.6 | H17B—C17—H17C | 109.5 |
C8—C7—C6 | 120.2 (2) | C16—C18—H18A | 109.5 |
C8—C7—H7A | 118.2 | C16—C18—H18B | 109.5 |
C6—C7—H7A | 121.6 | H18A—C18—H18B | 109.5 |
C9—N15—H15A | 109.2 (14) | C16—C18—H18C | 109.5 |
C9—N15—C16 | 118.89 (15) | H18A—C18—H18C | 109.5 |
C11—C9—C13 | 117.80 (17) | H18B—C18—H18C | 109.5 |
C11—C9—N15 | 122.89 (17) | C16—C19—H19A | 109.5 |
C13—C9—N15 | 119.26 (17) | C16—C19—H19B | 109.5 |
C12—N10—C14 | 117.62 (16) | H19A—C19—H19B | 109.5 |
C9—C11—C1 | 123.92 (17) | C16—C19—H19C | 109.5 |
C9—C11—C12 | 118.28 (17) | H19A—C19—H19C | 109.5 |
C1—C11—C12 | 117.79 (18) | H19B—C19—H19C | 109.5 |
N10—C12—C4 | 118.21 (17) | | |
| | | |
C11—C1—C2—C3 | −0.1 (3) | N15—C9—C13—C8 | −9.5 (3) |
C1—C2—C3—C4 | −0.2 (3) | C9—N15—H15A—C16 | 128.3 (7) |
C2—C3—C4—C12 | 0.1 (3) | C11—C9—C13—C14 | −8.7 (3) |
C14—C5—C6—C7 | −1.4 (3) | C11—C9—N15—H15A | −24.6 (14) |
C13—C8—C7—C6 | −0.6 (3) | N15—C9—C13—C14 | 173.62 (16) |
C5—C6—C7—C8 | 4.0 (3) | C7—C8—C13—C9 | 177.9 (2) |
C13—C9—C11—C1 | −174.09 (18) | C7—C8—C13—C14 | −5.1 (3) |
N15—C9—C11—C1 | 3.5 (3) | C12—N10—C14—C5 | −178.15 (17) |
C13—C9—C11—C12 | 6.7 (3) | C11—C9—N15—C16 | 95.3 (2) |
N15—C9—C11—C12 | −175.72 (16) | C12—N10—C14—C13 | 1.7 (3) |
C2—C1—C11—C9 | −178.64 (19) | C6—C5—C14—N10 | 175.50 (19) |
C2—C1—C11—C12 | 0.5 (3) | C6—C5—C14—C13 | −4.4 (3) |
C14—N10—C12—C4 | 177.18 (17) | C9—C13—C14—N10 | 4.7 (3) |
C14—N10—C12—C11 | −3.9 (3) | C8—C13—C14—N10 | −172.36 (18) |
C3—C4—C12—N10 | 179.41 (19) | C9—C13—C14—C5 | −175.46 (17) |
C3—C4—C12—C11 | 0.4 (3) | C8—C13—C14—C5 | 7.5 (3) |
C9—C11—C12—N10 | −0.4 (3) | C13—C9—N15—C16 | −87.2 (2) |
C1—C11—C12—N10 | −179.63 (18) | C9—N15—C16—C17 | −167.48 (18) |
C9—C11—C12—C4 | 178.55 (17) | C9—N15—C16—C18 | −48.2 (3) |
C1—C11—C12—C4 | −0.7 (3) | C9—N15—C16—C19 | 74.1 (2) |
C11—C9—C13—C8 | 168.16 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N15—H15A···N10i | 0.93 (2) | 2.38 (2) | 3.244 (3) | 154 (2) |
Symmetry code: (i) −x+1/2, y−1/2, z. |