The title compound, C16H15N3, shows a hindrance effect between adjacent amino and methyl groups that leads to a structural distortion, which is reflected in the non-planarity of the quinoline entity and in the bond angles and distances. The crystal packing consists of chains along the b axis sustained by an intermolecular hydrogen bond between the amino group and the N atom of the pyridyl ring.
Supporting information
CCDC reference: 645574
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXTL-Plus (Bruker, 1999); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: MaterialStudio (Accelrys, 2002); software used to prepare material for publication: SHELXTL-Plus.
4,6-Dimethyl-2-(3-pyridyl)quinolin-5-amine
top
Crystal data top
C16H15N3 | F(000) = 528 |
Mr = 249.31 | Dx = 1.300 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 21 reflections |
a = 9.397 (3) Å | θ = 20–26° |
b = 18.314 (2) Å | µ = 0.08 mm−1 |
c = 7.399 (4) Å | T = 298 K |
V = 1273.4 (8) Å3 | Irregular block, colourless |
Z = 4 | 0.54 × 0.48 × 0.40 mm |
Data collection top
Rigaku AFC-7S diffractometer | 1138 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω–2θ scans | h = −1→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→21 |
Tmin = 0.949, Tmax = 0.972 | l = 0→8 |
1447 measured reflections | 3 standard reflections every 150 reflections |
1309 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1555P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1309 reflections | Δρmax = 0.15 e Å−3 |
173 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.025 (4) |
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 >
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.9153 (2) | 0.42667 (11) | −0.0123 (3) | 0.0399 (5) | |
N2 | 1.1038 (3) | 0.67413 (12) | −0.1028 (4) | 0.0644 (8) | |
H2A | 1.1761 | 0.7027 | −0.0942 | 0.077* | |
H2B | 1.0274 | 0.6890 | −0.1552 | 0.077* | |
N3 | 0.6600 (3) | 0.25546 (12) | −0.1636 (4) | 0.0592 (7) | |
C1 | 0.7888 (3) | 0.44510 (13) | −0.0762 (3) | 0.0398 (6) | |
C2 | 0.7521 (3) | 0.51823 (13) | −0.1114 (4) | 0.0435 (6) | |
H2C | 0.6597 | 0.5293 | −0.1470 | 0.052* | |
C3 | 0.8495 (3) | 0.57342 (13) | −0.0944 (3) | 0.0419 (6) | |
C4 | 0.9910 (3) | 0.55483 (13) | −0.0414 (3) | 0.0374 (6) | |
C5 | 1.1104 (3) | 0.60344 (13) | −0.0317 (4) | 0.0436 (6) | |
C6 | 1.2355 (3) | 0.58178 (14) | 0.0514 (4) | 0.0459 (7) | |
C7 | 1.2492 (3) | 0.50951 (15) | 0.1124 (4) | 0.0489 (7) | |
H7 | 1.3323 | 0.4955 | 0.1711 | 0.059* | |
C8 | 1.1442 (3) | 0.45955 (13) | 0.0880 (4) | 0.0452 (7) | |
H8 | 1.1585 | 0.4114 | 0.1232 | 0.054* | |
C9 | 1.0140 (3) | 0.48030 (13) | 0.0097 (3) | 0.0380 (6) | |
C11 | 1.3600 (3) | 0.63368 (16) | 0.0729 (5) | 0.0677 (9) | |
H11B | 1.3301 | 0.6757 | 0.1405 | 0.102* | |
H11C | 1.3915 | 0.6499 | −0.0439 | 0.102* | |
H11A | 1.4386 | 0.6117 | 0.1354 | 0.102* | |
C10 | 0.7974 (3) | 0.65075 (13) | −0.1239 (4) | 0.0534 (7) | |
H10A | 0.8021 | 0.6635 | −0.2496 | 0.080* | |
H10B | 0.8561 | 0.6842 | −0.0573 | 0.080* | |
H10C | 0.7009 | 0.6536 | −0.0819 | 0.080* | |
C12 | 0.6869 (3) | 0.38412 (13) | −0.1032 (3) | 0.0410 (6) | |
C13 | 0.7389 (3) | 0.31504 (14) | −0.1437 (4) | 0.0477 (7) | |
H13 | 0.8368 | 0.3101 | −0.1580 | 0.057* | |
C14 | 0.5195 (3) | 0.26343 (17) | −0.1370 (5) | 0.0599 (8) | |
H14 | 0.4619 | 0.2222 | −0.1443 | 0.072* | |
C15 | 0.4568 (3) | 0.32930 (17) | −0.0997 (5) | 0.0574 (8) | |
H15 | 0.3587 | 0.3326 | −0.0851 | 0.069* | |
C16 | 0.5405 (3) | 0.39026 (16) | −0.0842 (4) | 0.0530 (7) | |
H16 | 0.4994 | 0.4355 | −0.0610 | 0.064* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0417 (11) | 0.0367 (10) | 0.0412 (11) | 0.0014 (10) | −0.0007 (10) | 0.0008 (9) |
N2 | 0.0633 (15) | 0.0413 (12) | 0.088 (2) | −0.0072 (12) | −0.0088 (17) | 0.0187 (13) |
N3 | 0.0554 (15) | 0.0513 (13) | 0.0710 (18) | −0.0064 (13) | 0.0036 (14) | −0.0093 (13) |
C1 | 0.0413 (14) | 0.0429 (13) | 0.0352 (13) | 0.0033 (12) | −0.0002 (12) | −0.0004 (11) |
C2 | 0.0434 (13) | 0.0439 (14) | 0.0433 (14) | 0.0083 (13) | −0.0049 (13) | 0.0004 (12) |
C3 | 0.0533 (15) | 0.0385 (12) | 0.0340 (13) | 0.0103 (12) | −0.0013 (13) | −0.0006 (11) |
C4 | 0.0419 (13) | 0.0374 (12) | 0.0329 (11) | 0.0046 (11) | 0.0024 (11) | −0.0002 (10) |
C5 | 0.0513 (15) | 0.0385 (13) | 0.0409 (14) | 0.0007 (13) | 0.0043 (13) | 0.0009 (11) |
C6 | 0.0452 (14) | 0.0484 (15) | 0.0442 (14) | −0.0051 (13) | −0.0030 (13) | −0.0018 (12) |
C7 | 0.0454 (13) | 0.0540 (16) | 0.0473 (15) | 0.0029 (13) | −0.0108 (14) | 0.0032 (14) |
C8 | 0.0443 (14) | 0.0417 (14) | 0.0497 (16) | 0.0037 (12) | −0.0058 (14) | 0.0050 (12) |
C9 | 0.0435 (14) | 0.0369 (12) | 0.0337 (12) | 0.0051 (11) | 0.0010 (11) | −0.0005 (11) |
C11 | 0.0627 (18) | 0.0664 (19) | 0.074 (2) | −0.0154 (17) | −0.0111 (19) | 0.0096 (18) |
C10 | 0.0583 (17) | 0.0433 (14) | 0.0587 (17) | 0.0113 (13) | −0.0038 (16) | 0.0032 (13) |
C12 | 0.0422 (13) | 0.0440 (14) | 0.0366 (13) | 0.0002 (12) | 0.0007 (13) | 0.0006 (12) |
C13 | 0.0436 (14) | 0.0455 (15) | 0.0540 (16) | 0.0002 (13) | 0.0009 (14) | −0.0060 (13) |
C14 | 0.0526 (18) | 0.0601 (18) | 0.067 (2) | −0.0143 (16) | −0.0022 (17) | −0.0069 (16) |
C15 | 0.0369 (14) | 0.0679 (19) | 0.0675 (19) | −0.0047 (14) | −0.0022 (15) | 0.0064 (17) |
C16 | 0.0468 (15) | 0.0540 (16) | 0.0582 (17) | 0.0075 (14) | −0.0012 (15) | 0.0022 (15) |
Geometric parameters (Å, º) top
N1—C1 | 1.323 (3) | C2—H2C | 0.9300 |
C1—C2 | 1.407 (3) | C6—C11 | 1.516 (4) |
C2—C3 | 1.369 (4) | C7—H7 | 0.9300 |
C3—C4 | 1.427 (4) | C8—H8 | 0.9300 |
C4—C5 | 1.434 (4) | C11—H11B | 0.9600 |
C5—C6 | 1.385 (4) | C11—H11C | 0.9600 |
C6—C7 | 1.404 (4) | C11—H11A | 0.9600 |
C7—C8 | 1.357 (4) | C10—H10A | 0.9600 |
C8—C9 | 1.406 (3) | C10—H10B | 0.9600 |
C9—N1 | 1.361 (3) | C10—H10C | 0.9600 |
C4—C9 | 1.433 (3) | C12—C16 | 1.387 (4) |
C1—C12 | 1.485 (3) | C12—C13 | 1.389 (3) |
C3—C10 | 1.514 (3) | C13—H13 | 0.9300 |
C5—N2 | 1.399 (3) | C14—C15 | 1.371 (4) |
N2—H2A | 0.8600 | C14—H14 | 0.9300 |
N2—H2B | 0.8600 | C15—C16 | 1.371 (4) |
N3—C13 | 1.327 (3) | C15—H15 | 0.9300 |
N3—C14 | 1.343 (4) | C16—H16 | 0.9300 |
| | | |
C1—N1—C9 | 118.1 (2) | N1—C9—C4 | 123.6 (2) |
C5—N2—H2A | 120.0 | C8—C9—C4 | 119.8 (2) |
C5—N2—H2B | 120.0 | C6—C11—H11B | 109.4 |
H2A—N2—H2B | 120.0 | C6—C11—H11C | 109.7 |
C13—N3—C14 | 116.3 (3) | H11B—C11—H11C | 108.2 |
N1—C1—C2 | 121.9 (2) | C6—C11—H11A | 112.4 |
N1—C1—C12 | 115.8 (2) | H11B—C11—H11A | 108.1 |
C2—C1—C12 | 122.2 (2) | H11C—C11—H11A | 109.1 |
C3—C2—C1 | 121.4 (2) | C3—C10—H10A | 110.6 |
C3—C2—H2C | 119.3 | C3—C10—H10B | 109.7 |
C1—C2—H2C | 119.3 | H10A—C10—H10B | 108.4 |
C2—C3—C4 | 118.2 (2) | C3—C10—H10C | 108.0 |
C2—C3—C10 | 117.4 (2) | H10A—C10—H10C | 110.1 |
C4—C3—C10 | 124.3 (2) | H10B—C10—H10C | 110.1 |
C3—C4—C9 | 116.1 (2) | C16—C12—C13 | 116.4 (3) |
C3—C4—C5 | 126.5 (2) | C16—C12—C1 | 124.4 (2) |
C9—C4—C5 | 117.4 (2) | C13—C12—C1 | 119.2 (2) |
C6—C5—N2 | 118.0 (2) | N3—C13—C12 | 125.2 (3) |
C6—C5—C4 | 120.6 (2) | N3—C13—H13 | 117.4 |
N2—C5—C4 | 121.4 (2) | C12—C13—H13 | 117.4 |
C5—C6—C7 | 119.3 (2) | N3—C14—C15 | 123.2 (3) |
C5—C6—C11 | 121.5 (2) | N3—C14—H14 | 118.4 |
C7—C6—C11 | 119.1 (2) | C15—C14—H14 | 118.4 |
C8—C7—C6 | 121.8 (3) | C14—C15—C16 | 119.1 (3) |
C8—C7—H7 | 119.1 | C14—C15—H15 | 120.4 |
C6—C7—H7 | 119.1 | C16—C15—H15 | 120.4 |
C7—C8—C9 | 120.3 (2) | C15—C16—C12 | 119.6 (3) |
C7—C8—H8 | 119.8 | C15—C16—H16 | 120.2 |
C9—C8—H8 | 119.8 | C12—C16—H16 | 120.2 |
N1—C9—C8 | 116.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···N2 | 0.96 | 2.36 | 2.915 (4) | 116 |
N2—H2A···N3i | 0.86 | 2.55 | 3.183 (4) | 131 |
C7—H7···CgAii | 0.93 | 2.74 | 3.405 (4) | 129 |
C10—H10A···CgBiii | 0.96 | 2.91 | 3.838 (4) | 162 |
Symmetry codes: (i) −x+2, y+1/2, −z−1/2; (ii) −x+5/2, −y+1, z+1/2; (iii) −x+3/2, −y+1, z−1/2. |