N-(3-Methyl-phen-yl)pyrimidin-2-amine.

Two independent mol-ecules comprise the asymmetric unit in the title compound, C(11)H(11)N(3). These differ in terms of the relative orientations of the aromatic rings: the first is somewhat twisted, while the second is approximately planar [dihedral angles between the pyrimidine and phenyl rings = 39.00 (8) and 4.59 (11)°]. The mol-ecules also form distinct patterns in their hydrogen bonding. The first independent mol-ecule forms centrosymmetric dimers featuring an eight-membered {HNCN}(2) synthon. The second independent mol-ecule forms an N-H⋯N hydrogen bond with the other pyrimidine N atom of the first mol-ecule. Thereby, tetra-meric aggregates are formed. These associate via C-H⋯N and C-H⋯π inter-actions, consolidating the crystal packing.

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For the structures of related pyrimidine amine derivatives, see: Badaruddin et al. (2009 ▶); Fairuz et al. (2010 ▶).

Experimental

Crystal data

C11H11N3

M = 185.23

Triclinic,

a = 9.4461 (10) Å

b = 10.0946 (11) Å

c = 11.6266 (13) Å

α = 80.401 (1)°

β = 82.745 (2)°

γ = 66.005 (1)°

V = 996.55 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

9569 measured reflections

4539 independent reflections

2881 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.167

S = 1.02

4539 reflections

264 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and Qmol (Gans & Shalloway, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033301/bt5328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033301/bt5328Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H11N3	Z = 4
Mr = 185.23	F(000) = 392
Triclinic, P1	Dx = 1.235 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4461 (10) Å	Cell parameters from 2493 reflections
b = 10.0946 (11) Å	θ = 4.4–24.7°
c = 11.6266 (13) Å	µ = 0.08 mm−1
α = 80.401 (1)°	T = 293 K
β = 82.745 (2)°	Block, colourless
γ = 66.005 (1)°	0.20 × 0.20 × 0.10 mm
V = 996.55 (19) Å3

Bruker SMART APEX diffractometer	2881 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −11→12
9569 measured reflections	k = −12→13
4539 independent reflections	l = −15→15

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)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0942P)2 + 0.0196P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4539 reflections	Δρmax = 0.24 e Å−3
264 parameters	Δρmin = −0.22 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (4)

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	0.78783 (16)	0.67552 (15)	0.14005 (12)	0.0480 (4)
N2	0.71434 (16)	0.88285 (15)	−0.00792 (12)	0.0511 (4)
N3	0.53298 (16)	0.84550 (16)	0.12674 (12)	0.0499 (4)
H3	0.4675 (17)	0.9178 (15)	0.0846 (14)	0.055 (5)*
N4	1.05919 (19)	0.15235 (17)	0.35892 (15)	0.0635 (4)
N5	1.0388 (2)	0.39503 (18)	0.35802 (17)	0.0721 (5)
N6	0.84789 (17)	0.35680 (16)	0.28605 (12)	0.0482 (4)
H6	0.810 (2)	0.4518 (10)	0.2708 (16)	0.060 (6)*
C1	0.68337 (19)	0.79917 (17)	0.08648 (13)	0.0425 (4)
C2	0.9333 (2)	0.6381 (2)	0.09545 (16)	0.0556 (5)
H2	1.0093	0.5542	0.1308	0.067*
C3	0.9782 (2)	0.7156 (2)	0.00069 (17)	0.0624 (5)
H3A	1.0811	0.6871	−0.0285	0.075*
C4	0.8615 (2)	0.8385 (2)	−0.04876 (16)	0.0574 (5)
H4	0.8872	0.8931	−0.1142	0.069*
C5	0.46706 (18)	0.78759 (16)	0.22835 (14)	0.0425 (4)
C6	0.5414 (2)	0.73374 (18)	0.33221 (14)	0.0485 (4)
H6A	0.6400	0.7313	0.3370	0.058*
C7	0.4663 (2)	0.6841 (2)	0.42779 (15)	0.0574 (5)
H7	0.5158	0.6464	0.4973	0.069*
C8	0.3197 (2)	0.6892 (2)	0.42267 (16)	0.0580 (5)
H8	0.2718	0.6544	0.4885	0.070*
C9	0.2421 (2)	0.74531 (17)	0.32074 (15)	0.0494 (4)
C10	0.31905 (19)	0.79320 (17)	0.22345 (15)	0.0458 (4)
H10	0.2700	0.8297	0.1537	0.055*
C11	0.0801 (2)	0.7550 (2)	0.3143 (2)	0.0685 (6)
H11A	0.0143	0.8042	0.3771	0.103*
H11B	0.0818	0.6583	0.3207	0.103*
H11C	0.0408	0.8086	0.2409	0.103*
C12	0.9877 (2)	0.29674 (18)	0.33629 (14)	0.0464 (4)
C13	1.1733 (3)	0.3396 (3)	0.4079 (2)	0.0846 (7)
H13	1.2123	0.4041	0.4260	0.102*
C14	1.2576 (2)	0.1932 (3)	0.4342 (2)	0.0733 (6)
H14	1.3522	0.1572	0.4682	0.088*
C15	1.1951 (2)	0.1040 (2)	0.4078 (2)	0.0715 (6)
H15	1.2494	0.0036	0.4245	0.086*
C16	0.75431 (19)	0.29091 (18)	0.25653 (14)	0.0444 (4)
C17	0.7885 (3)	0.1426 (2)	0.2762 (2)	0.0712 (6)
H17	0.8790	0.0783	0.3110	0.085*
C18	0.6869 (3)	0.0911 (2)	0.2434 (3)	0.0877 (8)
H18	0.7101	−0.0087	0.2572	0.105*
C19	0.5535 (3)	0.1820 (2)	0.1916 (2)	0.0752 (6)
H19	0.4879	0.1438	0.1696	0.090*
C20	0.5161 (2)	0.3304 (2)	0.17184 (17)	0.0576 (5)
C21	0.6174 (2)	0.38285 (19)	0.20499 (15)	0.0511 (4)
H21	0.5930	0.4829	0.1923	0.061*
C22	0.3675 (3)	0.4331 (3)	0.1169 (2)	0.0877 (8)
H22A	0.2841	0.4052	0.1508	0.132*
H22B	0.3793	0.4284	0.0343	0.132*
H22C	0.3446	0.5312	0.1307	0.132*

	U11	U22	U33	U12	U13	U23
N1	0.0448 (8)	0.0418 (8)	0.0489 (8)	−0.0109 (6)	−0.0080 (6)	0.0043 (6)
N2	0.0493 (9)	0.0483 (8)	0.0462 (8)	−0.0143 (7)	−0.0032 (6)	0.0064 (6)
N3	0.0418 (8)	0.0474 (8)	0.0475 (8)	−0.0107 (7)	−0.0077 (6)	0.0143 (6)
N4	0.0607 (10)	0.0478 (9)	0.0775 (11)	−0.0105 (8)	−0.0246 (8)	−0.0092 (8)
N5	0.0761 (12)	0.0559 (10)	0.0930 (13)	−0.0330 (9)	−0.0399 (10)	0.0119 (9)
N6	0.0512 (8)	0.0402 (8)	0.0525 (8)	−0.0177 (7)	−0.0127 (7)	0.0020 (6)
C1	0.0456 (9)	0.0385 (8)	0.0404 (8)	−0.0144 (7)	−0.0086 (7)	0.0015 (6)
C2	0.0466 (10)	0.0502 (10)	0.0570 (11)	−0.0077 (8)	−0.0090 (8)	0.0016 (8)
C3	0.0473 (10)	0.0673 (12)	0.0577 (11)	−0.0125 (9)	0.0037 (8)	−0.0002 (9)
C4	0.0563 (11)	0.0601 (11)	0.0470 (10)	−0.0200 (9)	0.0022 (8)	0.0042 (8)
C5	0.0454 (9)	0.0329 (8)	0.0435 (8)	−0.0112 (7)	−0.0037 (7)	0.0006 (6)
C6	0.0511 (10)	0.0465 (9)	0.0459 (9)	−0.0178 (8)	−0.0091 (7)	0.0002 (7)
C7	0.0656 (12)	0.0569 (11)	0.0439 (9)	−0.0205 (9)	−0.0103 (8)	0.0045 (8)
C8	0.0694 (13)	0.0531 (11)	0.0475 (10)	−0.0263 (10)	0.0060 (9)	0.0025 (8)
C9	0.0498 (10)	0.0371 (9)	0.0579 (10)	−0.0154 (8)	0.0013 (8)	−0.0055 (7)
C10	0.0477 (10)	0.0379 (9)	0.0472 (9)	−0.0132 (7)	−0.0069 (7)	−0.0002 (7)
C11	0.0579 (12)	0.0648 (13)	0.0832 (14)	−0.0285 (10)	0.0022 (10)	−0.0046 (11)
C12	0.0487 (10)	0.0473 (10)	0.0418 (8)	−0.0184 (8)	−0.0072 (7)	0.0003 (7)
C13	0.0835 (16)	0.0721 (15)	0.1102 (19)	−0.0391 (13)	−0.0499 (14)	0.0114 (13)
C14	0.0601 (13)	0.0768 (15)	0.0808 (14)	−0.0206 (11)	−0.0286 (11)	−0.0028 (11)
C15	0.0639 (13)	0.0549 (12)	0.0852 (15)	−0.0046 (10)	−0.0276 (11)	−0.0132 (10)
C16	0.0460 (9)	0.0450 (9)	0.0418 (8)	−0.0181 (8)	−0.0038 (7)	−0.0031 (7)
C17	0.0688 (13)	0.0477 (11)	0.1000 (16)	−0.0234 (10)	−0.0330 (12)	0.0043 (11)
C18	0.0877 (16)	0.0487 (12)	0.137 (2)	−0.0316 (12)	−0.0446 (15)	0.0017 (13)
C19	0.0666 (13)	0.0669 (14)	0.1044 (18)	−0.0318 (11)	−0.0199 (12)	−0.0187 (12)
C20	0.0494 (10)	0.0616 (12)	0.0615 (11)	−0.0174 (9)	−0.0082 (8)	−0.0150 (9)
C21	0.0509 (10)	0.0442 (9)	0.0555 (10)	−0.0140 (8)	−0.0091 (8)	−0.0072 (8)
C22	0.0640 (14)	0.0809 (16)	0.117 (2)	−0.0156 (12)	−0.0360 (13)	−0.0204 (14)

N1—C2	1.328 (2)	C8—H8	0.9300
N1—C1	1.347 (2)	C9—C10	1.392 (2)
N2—C4	1.325 (2)	C9—C11	1.504 (3)
N2—C1	1.3470 (19)	C10—H10	0.9300
N3—C1	1.349 (2)	C11—H11A	0.9600
N3—C5	1.416 (2)	C11—H11B	0.9600
N3—H3	0.863 (9)	C11—H11C	0.9600
N4—C12	1.329 (2)	C13—C14	1.365 (3)
N4—C15	1.339 (2)	C13—H13	0.9300
N5—C13	1.328 (3)	C14—C15	1.351 (3)
N5—C12	1.336 (2)	C14—H14	0.9300
N6—C12	1.371 (2)	C15—H15	0.9300
N6—C16	1.404 (2)	C16—C17	1.381 (2)
N6—H6	0.872 (9)	C16—C21	1.388 (2)
C2—C3	1.367 (2)	C17—C18	1.378 (3)
C2—H2	0.9300	C17—H17	0.9300
C3—C4	1.376 (3)	C18—C19	1.364 (3)
C3—H3A	0.9300	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.378 (3)
C5—C10	1.384 (2)	C19—H19	0.9300
C5—C6	1.390 (2)	C20—C21	1.385 (2)
C6—C7	1.376 (2)	C20—C22	1.508 (3)
C6—H6A	0.9300	C21—H21	0.9300
C7—C8	1.374 (3)	C22—H22A	0.9600
C7—H7	0.9300	C22—H22B	0.9600
C8—C9	1.386 (3)	C22—H22C	0.9600
C2—N1—C1	115.41 (14)	C9—C11—H11B	109.5
C4—N2—C1	115.85 (14)	H11A—C11—H11B	109.5
C1—N3—C5	128.18 (13)	C9—C11—H11C	109.5
C1—N3—H3	116.6 (12)	H11A—C11—H11C	109.5
C5—N3—H3	115.1 (12)	H11B—C11—H11C	109.5
C12—N4—C15	115.44 (18)	N4—C12—N5	126.19 (16)
C13—N5—C12	115.19 (17)	N4—C12—N6	119.78 (16)
C12—N6—C16	130.75 (14)	N5—C12—N6	114.03 (15)
C12—N6—H6	114.5 (13)	N5—C13—C14	123.7 (2)
C16—N6—H6	114.7 (13)	N5—C13—H13	118.1
N1—C1—N2	125.62 (15)	C14—C13—H13	118.1
N1—C1—N3	119.24 (14)	C15—C14—C13	115.9 (2)
N2—C1—N3	115.13 (14)	C15—C14—H14	122.0
N1—C2—C3	123.91 (16)	C13—C14—H14	122.0
N1—C2—H2	118.0	N4—C15—C14	123.5 (2)
C3—C2—H2	118.0	N4—C15—H15	118.3
C2—C3—C4	115.81 (17)	C14—C15—H15	118.3
C2—C3—H3A	122.1	C17—C16—C21	118.40 (16)
C4—C3—H3A	122.1	C17—C16—N6	124.64 (16)
N2—C4—C3	123.38 (16)	C21—C16—N6	116.96 (15)
N2—C4—H4	118.3	C18—C17—C16	119.19 (19)
C3—C4—H4	118.3	C18—C17—H17	120.4
C10—C5—C6	119.87 (15)	C16—C17—H17	120.4
C10—C5—N3	117.36 (14)	C19—C18—C17	122.1 (2)
C6—C5—N3	122.68 (15)	C19—C18—H18	119.0
C7—C6—C5	118.69 (16)	C17—C18—H18	119.0
C7—C6—H6A	120.7	C18—C19—C20	119.86 (19)
C5—C6—H6A	120.7	C18—C19—H19	120.1
C8—C7—C6	121.37 (17)	C20—C19—H19	120.1
C8—C7—H7	119.3	C19—C20—C21	118.31 (18)
C6—C7—H7	119.3	C19—C20—C22	120.71 (18)
C7—C8—C9	120.87 (16)	C21—C20—C22	120.98 (18)
C7—C8—H8	119.6	C20—C21—C16	122.16 (17)
C9—C8—H8	119.6	C20—C21—H21	118.9
C8—C9—C10	117.80 (16)	C16—C21—H21	118.9
C8—C9—C11	121.64 (16)	C20—C22—H22A	109.5
C10—C9—C11	120.56 (17)	C20—C22—H22B	109.5
C5—C10—C9	121.37 (16)	H22A—C22—H22B	109.5
C5—C10—H10	119.3	C20—C22—H22C	109.5
C9—C10—H10	119.3	H22A—C22—H22C	109.5
C9—C11—H11A	109.5	H22B—C22—H22C	109.5
C2—N1—C1—N2	1.8 (3)	C15—N4—C12—N5	−0.2 (3)
C2—N1—C1—N3	−179.59 (15)	C15—N4—C12—N6	179.91 (17)
C4—N2—C1—N1	−1.1 (3)	C13—N5—C12—N4	−0.6 (3)
C4—N2—C1—N3	−179.76 (15)	C13—N5—C12—N6	179.29 (19)
C5—N3—C1—N1	6.3 (3)	C16—N6—C12—N4	3.7 (3)
C5—N3—C1—N2	−174.88 (16)	C16—N6—C12—N5	−176.17 (17)
C1—N1—C2—C3	−1.0 (3)	C12—N5—C13—C14	1.2 (4)
N1—C2—C3—C4	−0.3 (3)	N5—C13—C14—C15	−0.9 (4)
C1—N2—C4—C3	−0.4 (3)	C12—N4—C15—C14	0.5 (3)
C2—C3—C4—N2	1.1 (3)	C13—C14—C15—N4	0.0 (4)
C1—N3—C5—C10	−146.27 (17)	C12—N6—C16—C17	1.1 (3)
C1—N3—C5—C6	37.2 (3)	C12—N6—C16—C21	−179.49 (16)
C10—C5—C6—C7	1.3 (2)	C21—C16—C17—C18	0.4 (3)
N3—C5—C6—C7	177.79 (16)	N6—C16—C17—C18	179.8 (2)
C5—C6—C7—C8	−1.0 (3)	C16—C17—C18—C19	0.3 (4)
C6—C7—C8—C9	−0.3 (3)	C17—C18—C19—C20	−0.8 (4)
C7—C8—C9—C10	1.4 (3)	C18—C19—C20—C21	0.5 (3)
C7—C8—C9—C11	−178.53 (18)	C18—C19—C20—C22	−178.7 (2)
C6—C5—C10—C9	−0.2 (2)	C19—C20—C21—C16	0.3 (3)
N3—C5—C10—C9	−176.90 (15)	C22—C20—C21—C16	179.48 (19)
C8—C9—C10—C5	−1.1 (2)	C17—C16—C21—C20	−0.7 (3)
C11—C9—C10—C5	178.82 (16)	N6—C16—C21—C20	179.82 (16)

Cg1 and Cg2 are the centroids of the N4,N5,C12–C15 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N2i	0.86 (1)	2.19 (1)	3.0377 (19)	170.(2)
N6—H6···N1	0.87 (1)	2.45 (1)	3.2391 (19)	151.(2)
C6—H6a···N1	0.93	2.55	2.961 (2)	107
C17—H17···N4	0.93	2.28	2.886 (3)	123
C11—H11a···Cg1ii	0.96	2.96	3.766 (2)	143
C15—H15···Cg2iii	0.93	2.82	3.620 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N4,N5,C12–C15 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N2i	0.86 (1)	2.19 (1)	3.0377 (19)	170 (2)
N6—H6⋯N1	0.87 (1)	2.45 (1)	3.2391 (19)	151 (2)
C6—H6a⋯N1	0.93	2.55	2.961 (2)	107
C17—H17⋯N4	0.93	2.28	2.886 (3)	123
C11—H11a⋯Cg1ii	0.96	2.96	3.766 (2)	143
C15—H15⋯Cg2iii	0.93	2.82	3.620 (2)	144

Symmetry codes: (i) ; (ii) ; (iii) .