4-Methyl-6-phenyl-pyrimidin-2-amine.

The title compound, C(11)H(11)N(3), was synthesized as part of our research into functionalized pyrimidines. It crystallizes with two independent mol-ecules in the asymmetric unit that differ only in the twist between the two aromatic rings; the torsion angles between the rings are 29.9 (2) and 45.1 (2)°. The crystal packing is dominated by inter-molecular N-H⋯N hydrogen bonds between independent and equivalent mol-ecules, forming an infinite three-dimensional network.

Related literature

For biological activity, see: Zhu & Yang (2005 ▶); Sherrington & Taskinen (2001 ▶); Ligthart et al. (2005 ▶). For a similar structure, see: Fun et al. (2006 ▶).

Experimental

Crystal data

C11H11N3

M = 185.23

Monoclinic,

a = 14.0558 (11) Å

b = 9.3808 (7) Å

c = 18.5227 (12) Å

β = 125.950 (4)°

V = 1977.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 273 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.977, T max = 0.985

17472 measured reflections

3619 independent reflections

2760 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.04

3619 reflections

256 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2001 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks h-1, I. DOI: 10.1107/S1600536808008003/fl2182sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008003/fl2182Isup2.hkl

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

C11H11N3	F000 = 784
Mr = 185.23	Dx = 1.245 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 512 reflections
a = 14.0558 (11) Å	θ = 2–22º
b = 9.3808 (7) Å	µ = 0.08 mm−1
c = 18.5227 (12) Å	T = 273 (2) K
β = 125.950 (4)º	Block, colorless
V = 1977.1 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker SMART 1K CCD area-detector diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	2760 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
T = 295(2) K	θmax = 25.4º
thin–slice ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −14→16
Tmin = 0.977, Tmax = 0.985	k = −11→11
17472 measured reflections	l = −22→20

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.393P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.21 e Å−3
3619 reflections	Δρmin = −0.16 e Å−3
256 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (13)
Secondary atom site location: difference Fourier map

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	1.09631 (12)	−0.10203 (14)	0.46842 (9)	0.0492 (4)
H1A	1.0775	−0.1072	0.5049	0.059*
H1B	1.1590	−0.1434	0.4810	0.059*
N2	1.06247 (11)	−0.02652 (14)	0.33737 (9)	0.0445 (3)
N3	0.93111 (10)	0.03294 (12)	0.37592 (8)	0.0371 (3)
C1	0.69500 (14)	0.10273 (16)	0.31097 (10)	0.0428 (4)
H1C	0.7276	0.0232	0.3478	0.051*
C2	0.59049 (15)	0.1585 (2)	0.28979 (12)	0.0537 (4)
H2B	0.5531	0.1161	0.3123	0.064*
C3	0.54156 (17)	0.2762 (2)	0.23573 (13)	0.0661 (5)
H3B	0.4718	0.3143	0.2223	0.079*
C4	0.59617 (19)	0.3378 (2)	0.20139 (14)	0.0711 (6)
H4A	0.5627	0.4168	0.1642	0.085*
C5	0.70011 (16)	0.28266 (19)	0.22208 (12)	0.0557 (5)
H5A	0.7363	0.3249	0.1986	0.067*
C6	0.75185 (13)	0.16463 (15)	0.27758 (10)	0.0395 (4)
C7	0.86232 (13)	0.10283 (14)	0.29811 (10)	0.0370 (3)
C8	0.89113 (14)	0.11063 (17)	0.23828 (11)	0.0462 (4)
H8A	0.8435	0.1598	0.1847	0.055*
C9	1.02765 (13)	−0.02917 (15)	0.39158 (10)	0.0371 (3)
C10	0.99219 (14)	0.04372 (18)	0.26026 (11)	0.0457 (4)
C11	1.02670 (19)	0.0447 (3)	0.19755 (13)	0.0730 (6)
H11A	1.1108	0.0476	0.2311	0.109*
H11B	0.9937	0.1271	0.1597	0.109*
H11C	0.9977	−0.0400	0.1616	0.109*
N4	0.66133 (12)	0.04458 (13)	0.54000 (9)	0.0466 (4)
H4B	0.6190	−0.0240	0.5377	0.056*
H4C	0.7366	0.0363	0.5722	0.056*
N5	0.49149 (11)	0.17062 (13)	0.44429 (9)	0.0440 (3)
N6	0.68078 (11)	0.26712 (12)	0.49771 (8)	0.0379 (3)
C12	0.78707 (15)	0.46852 (17)	0.44133 (12)	0.0494 (4)
H12A	0.7997	0.3741	0.4339	0.059*
C13	0.85244 (17)	0.5759 (2)	0.43871 (13)	0.0597 (5)
H13A	0.9080	0.5533	0.4285	0.072*
C14	0.83596 (17)	0.7156 (2)	0.45107 (13)	0.0644 (5)
H14A	0.8809	0.7871	0.4499	0.077*
C15	0.75362 (19)	0.74936 (19)	0.46501 (15)	0.0683 (6)
H15A	0.7429	0.8438	0.4740	0.082*
C16	0.68603 (17)	0.64335 (17)	0.46588 (13)	0.0566 (5)
H16A	0.6286	0.6674	0.4738	0.068*
C17	0.70284 (13)	0.50159 (15)	0.45505 (10)	0.0404 (4)
C18	0.62748 (13)	0.38817 (15)	0.45327 (10)	0.0387 (4)
C19	0.50733 (14)	0.40570 (17)	0.40489 (11)	0.0471 (4)
H19A	0.4721	0.4919	0.3770	0.057*
C20	0.60975 (13)	0.16496 (15)	0.49325 (10)	0.0376 (3)
C21	0.44081 (14)	0.29142 (17)	0.39901 (11)	0.0475 (4)
C22	0.30886 (16)	0.2934 (2)	0.33834 (15)	0.0744 (6)
H22A	0.2787	0.2262	0.3593	0.112*
H22B	0.2823	0.2681	0.2790	0.112*
H22C	0.2812	0.3872	0.3379	0.112*

	U11	U22	U33	U12	U13	U23
N1	0.0443 (8)	0.0635 (8)	0.0430 (8)	0.0156 (6)	0.0274 (7)	0.0176 (7)
N2	0.0398 (7)	0.0573 (8)	0.0382 (8)	0.0040 (6)	0.0239 (7)	0.0047 (6)
N3	0.0349 (7)	0.0422 (6)	0.0335 (7)	0.0002 (5)	0.0196 (6)	0.0031 (5)
C1	0.0399 (9)	0.0490 (8)	0.0359 (9)	−0.0024 (7)	0.0202 (8)	−0.0030 (7)
C2	0.0455 (10)	0.0717 (11)	0.0479 (10)	−0.0032 (9)	0.0296 (9)	−0.0102 (9)
C3	0.0497 (11)	0.0876 (14)	0.0552 (12)	0.0223 (10)	0.0275 (10)	0.0005 (10)
C4	0.0712 (13)	0.0751 (13)	0.0652 (13)	0.0330 (11)	0.0391 (12)	0.0220 (10)
C5	0.0577 (11)	0.0579 (10)	0.0533 (11)	0.0135 (8)	0.0335 (10)	0.0141 (8)
C6	0.0377 (8)	0.0430 (8)	0.0328 (8)	0.0007 (6)	0.0179 (7)	−0.0014 (6)
C7	0.0351 (8)	0.0379 (7)	0.0334 (8)	−0.0026 (6)	0.0175 (7)	0.0012 (6)
C8	0.0432 (9)	0.0582 (9)	0.0353 (9)	0.0052 (7)	0.0220 (8)	0.0109 (7)
C9	0.0345 (8)	0.0403 (7)	0.0341 (8)	−0.0017 (6)	0.0187 (7)	0.0013 (6)
C10	0.0414 (9)	0.0617 (10)	0.0351 (9)	0.0007 (7)	0.0230 (8)	0.0039 (7)
C11	0.0642 (13)	0.1156 (17)	0.0521 (12)	0.0198 (12)	0.0414 (11)	0.0190 (11)
N4	0.0396 (7)	0.0426 (7)	0.0574 (9)	0.0040 (6)	0.0284 (7)	0.0128 (6)
N5	0.0377 (7)	0.0477 (7)	0.0461 (8)	0.0007 (6)	0.0243 (7)	0.0095 (6)
N6	0.0385 (7)	0.0396 (6)	0.0385 (7)	−0.0002 (5)	0.0242 (6)	0.0026 (5)
C12	0.0520 (10)	0.0467 (9)	0.0570 (11)	0.0015 (7)	0.0363 (9)	0.0049 (7)
C13	0.0559 (11)	0.0681 (11)	0.0666 (13)	−0.0038 (9)	0.0425 (10)	0.0081 (9)
C14	0.0619 (12)	0.0561 (11)	0.0710 (13)	−0.0176 (9)	0.0367 (11)	0.0032 (9)
C15	0.0769 (14)	0.0424 (9)	0.0895 (16)	−0.0120 (9)	0.0510 (13)	−0.0080 (9)
C16	0.0621 (11)	0.0473 (9)	0.0710 (12)	−0.0024 (8)	0.0449 (10)	−0.0038 (8)
C17	0.0416 (8)	0.0405 (8)	0.0381 (9)	−0.0007 (6)	0.0229 (7)	0.0038 (6)
C18	0.0429 (9)	0.0397 (8)	0.0378 (9)	0.0014 (6)	0.0260 (8)	0.0023 (6)
C19	0.0448 (10)	0.0448 (8)	0.0519 (10)	0.0071 (7)	0.0286 (9)	0.0139 (7)
C20	0.0391 (8)	0.0406 (7)	0.0366 (8)	0.0011 (6)	0.0243 (7)	0.0016 (6)
C21	0.0399 (9)	0.0543 (9)	0.0481 (10)	0.0049 (7)	0.0258 (8)	0.0125 (8)
C22	0.0415 (10)	0.0858 (14)	0.0792 (15)	0.0059 (10)	0.0261 (11)	0.0336 (12)

N1—C9	1.3459 (19)	N4—C20	1.3467 (19)
N1—H1A	0.8600	N4—H4B	0.8600
N1—H1B	0.8600	N4—H4C	0.8600
N2—C10	1.339 (2)	N5—C21	1.339 (2)
N2—C9	1.3509 (19)	N5—C20	1.3484 (19)
N3—C9	1.3426 (19)	N6—C18	1.3431 (18)
N3—C7	1.3437 (18)	N6—C20	1.3510 (18)
C1—C2	1.382 (2)	C12—C13	1.383 (2)
C1—C6	1.392 (2)	C12—C17	1.384 (2)
C1—H1C	0.9300	C12—H12A	0.9300
C2—C3	1.374 (3)	C13—C14	1.373 (3)
C2—H2B	0.9300	C13—H13A	0.9300
C3—C4	1.379 (3)	C14—C15	1.363 (3)
C3—H3B	0.9300	C14—H14A	0.9300
C4—C5	1.375 (3)	C15—C16	1.382 (2)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.391 (2)	C16—C17	1.386 (2)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.483 (2)	C17—C18	1.488 (2)
C7—C8	1.387 (2)	C18—C19	1.380 (2)
C8—C10	1.378 (2)	C19—C21	1.384 (2)
C8—H8A	0.9300	C19—H19A	0.9300
C10—C11	1.499 (2)	C21—C22	1.502 (2)
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
C9—N1—H1A	120.0	C20—N4—H4B	120.0
C9—N1—H1B	120.0	C20—N4—H4C	120.0
H1A—N1—H1B	120.0	H4B—N4—H4C	120.0
C10—N2—C9	116.07 (13)	C21—N5—C20	116.55 (13)
C9—N3—C7	116.30 (12)	C18—N6—C20	115.84 (12)
C2—C1—C6	120.52 (15)	C13—C12—C17	120.02 (16)
C2—C1—H1C	119.7	C13—C12—H12A	120.0
C6—C1—H1C	119.7	C17—C12—H12A	120.0
C3—C2—C1	120.35 (17)	C14—C13—C12	120.58 (17)
C3—C2—H2B	119.8	C14—C13—H13A	119.7
C1—C2—H2B	119.8	C12—C13—H13A	119.7
C2—C3—C4	119.81 (17)	C15—C14—C13	119.89 (16)
C2—C3—H3B	120.1	C15—C14—H14A	120.1
C4—C3—H3B	120.1	C13—C14—H14A	120.1
C5—C4—C3	120.12 (18)	C14—C15—C16	120.07 (17)
C5—C4—H4A	119.9	C14—C15—H15A	120.0
C3—C4—H4A	119.9	C16—C15—H15A	120.0
C4—C5—C6	120.95 (18)	C15—C16—C17	120.81 (17)
C4—C5—H5A	119.5	C15—C16—H16A	119.6
C6—C5—H5A	119.5	C17—C16—H16A	119.6
C5—C6—C1	118.24 (15)	C12—C17—C16	118.59 (15)
C5—C6—C7	121.01 (14)	C12—C17—C18	120.67 (14)
C1—C6—C7	120.72 (13)	C16—C17—C18	120.65 (14)
N3—C7—C8	121.26 (14)	N6—C18—C19	121.89 (13)
N3—C7—C6	116.84 (13)	N6—C18—C17	117.21 (13)
C8—C7—C6	121.83 (14)	C19—C18—C17	120.86 (13)
C10—C8—C7	118.27 (14)	C18—C19—C21	118.12 (14)
C10—C8—H8A	120.9	C18—C19—H19A	120.9
C7—C8—H8A	120.9	C21—C19—H19A	120.9
N3—C9—N1	117.08 (13)	N4—C20—N5	116.82 (13)
N3—C9—N2	126.34 (13)	N4—C20—N6	117.13 (13)
N1—C9—N2	116.58 (13)	N5—C20—N6	126.02 (13)
N2—C10—C8	121.75 (14)	N5—C21—C19	121.31 (14)
N2—C10—C11	117.25 (15)	N5—C21—C22	116.64 (15)
C8—C10—C11	120.99 (15)	C19—C21—C22	121.98 (15)
C10—C11—H11A	109.5	C21—C22—H22A	109.5
C10—C11—H11B	109.5	C21—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C10—C11—H11C	109.5	C21—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5
C6—C1—C2—C3	−0.3 (2)	C17—C12—C13—C14	1.1 (3)
C1—C2—C3—C4	0.9 (3)	C12—C13—C14—C15	−0.8 (3)
C2—C3—C4—C5	−0.8 (3)	C13—C14—C15—C16	−0.6 (3)
C3—C4—C5—C6	0.0 (3)	C14—C15—C16—C17	1.7 (3)
C4—C5—C6—C1	0.7 (3)	C13—C12—C17—C16	0.0 (3)
C4—C5—C6—C7	178.44 (17)	C13—C12—C17—C18	176.76 (16)
C2—C1—C6—C5	−0.5 (2)	C15—C16—C17—C12	−1.4 (3)
C2—C1—C6—C7	−178.31 (14)	C15—C16—C17—C18	−178.14 (17)
C9—N3—C7—C8	−0.6 (2)	C20—N6—C18—C19	−1.1 (2)
C9—N3—C7—C6	176.50 (12)	C20—N6—C18—C17	−178.59 (13)
C5—C6—C7—N3	153.34 (15)	C12—C17—C18—N6	45.1 (2)
C1—C6—C7—N3	−28.9 (2)	C16—C17—C18—N6	−138.24 (16)
C5—C6—C7—C8	−29.6 (2)	C12—C17—C18—C19	−132.43 (17)
C1—C6—C7—C8	148.13 (15)	C16—C17—C18—C19	44.2 (2)
N3—C7—C8—C10	0.5 (2)	N6—C18—C19—C21	−3.4 (2)
C6—C7—C8—C10	−176.46 (14)	C17—C18—C19—C21	174.05 (15)
C7—N3—C9—N1	−178.71 (13)	C21—N5—C20—N4	179.01 (14)
C7—N3—C9—N2	0.8 (2)	C21—N5—C20—N6	−2.9 (2)
C10—N2—C9—N3	−0.9 (2)	C18—N6—C20—N4	−177.49 (13)
C10—N2—C9—N1	178.64 (14)	C18—N6—C20—N5	4.5 (2)
C9—N2—C10—C8	0.7 (2)	C20—N5—C21—C19	−2.0 (2)
C9—N2—C10—C11	−178.21 (16)	C20—N5—C21—C22	174.92 (16)
C7—C8—C10—N2	−0.6 (2)	C18—C19—C21—N5	5.0 (3)
C7—C8—C10—C11	178.35 (17)	C18—C19—C21—C22	−171.76 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3i	0.86	2.38	3.1918 (18)	157
N1—H1B···N6i	0.86	2.35	3.2095 (18)	175
N4—H4C···N2i	0.86	2.29	3.1474 (19)	176
N4—H4B···N5ii	0.86	2.24	3.0834 (18)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3i	0.86	2.38	3.1918 (18)	157
N1—H1B⋯N6i	0.86	2.35	3.2095 (18)	175
N4—H4C⋯N2i	0.86	2.29	3.1474 (19)	176
N4—H4B⋯N5ii	0.86	2.24	3.0834 (18)	166

Symmetry codes: (i) ; (ii) .