9-(tert-Butyl­amino)­acridine

The crystal structure of 9-(tert-butyl­amino)­acridine, C₁₇H₁₈N₂, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

---

Computing details

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

Crystal data

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) Å^3	Needle, yellow
Z = 8	0.6 × 0.4 × 0.3 mm
F(000) = 1072

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 0.3081P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N15—H15A···N10^i	0.93 (2)	2.38 (2)	3.244 (3)	154 (2)

Symmetry code: (i) −x+1/2, y−1/2, z.