4,6-Dimethyl-2-(3-pyrid­yl)quinolin-5-amine

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.

Computing details

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

Crystal data

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) Å^3	Irregular block, colourless
Z = 4	0.54 × 0.48 × 0.40 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0607P)^2 + 0.1555P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (4)

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 > 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 (Ų)

	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 (Ų)

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

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)

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···N3^i	0.86	2.55	3.183 (4)	131
C7—H7···CgA^ii	0.93	2.74	3.405 (4)	129
C10—H10A···CgB^iii	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.