N-(Pyrimidin-2-yl)aniline.

There are two molecules in the asymmetric unit of the title compound, C(10)H(9)N(3), with inter-ring dihedral angles of 31.1 (1) and 35.3 (1)°. The bridging C-N-C bond angles are 128.2 (1) and 129.1 (1)°. In the crystal, the two independent mol-ecules are linked into a dimer by two N-H⋯N hydrogen bonds.

Related literature

For the structure of 4-chloro-N-(pyrimidin-2-yl)aniline, see: Maizathul Akmam et al. (2009 ▶).

Experimental

Crystal data

C10H9N3

M = 171.20

Triclinic,

a = 8.8792 (2) Å

b = 9.9382 (2) Å

c = 10.2038 (2) Å

α = 93.186 (1)°

β = 103.665 (1)°

γ = 97.780 (1)°

V = 863.28 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 123 K

0.35 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

8238 measured reflections

3950 independent reflections

3144 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.03

3950 reflections

243 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007685/xu2492sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007685/xu2492Isup2.hkl

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

C10H9N3	Z = 4
Mr = 171.20	F(000) = 360
Triclinic, P1	Dx = 1.317 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8792 (2) Å	Cell parameters from 3015 reflections
b = 9.9382 (2) Å	θ = 2.7–28.3°
c = 10.2038 (2) Å	µ = 0.08 mm−1
α = 93.186 (1)°	T = 123 K
β = 103.665 (1)°	Prism, colorless
γ = 97.780 (1)°	0.35 × 0.20 × 0.10 mm
V = 863.28 (3) Å3

Bruker SMART APEX diffractometer	3144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 27.5°, θmin = 2.1°
ω scans	h = −11→11
8238 measured reflections	k = −12→12
3950 independent reflections	l = −13→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.056P)2 + 0.1316P] where P = (Fo2 + 2Fc2)/3
3950 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

	x	y	z	Uiso*/Ueq
N1	0.63241 (11)	0.69760 (10)	0.39973 (10)	0.0229 (2)
H1	0.5458 (13)	0.7328 (15)	0.4021 (15)	0.042 (4)*
N2	0.60532 (11)	0.62876 (10)	0.60461 (10)	0.0235 (2)
N3	0.82465 (11)	0.58169 (10)	0.51919 (10)	0.0257 (2)
N4	0.33475 (12)	0.78540 (10)	0.59499 (10)	0.0256 (2)
H4	0.4034 (15)	0.7306 (13)	0.5833 (14)	0.038 (4)*
N5	0.37902 (11)	0.86480 (10)	0.39948 (10)	0.0256 (2)
N6	0.18856 (11)	0.94997 (10)	0.50126 (10)	0.0245 (2)
C1	0.69680 (13)	0.72230 (11)	0.28811 (11)	0.0212 (2)
C2	0.59235 (14)	0.72964 (12)	0.16374 (12)	0.0259 (3)
H2	0.4827	0.7163	0.1571	0.031*
C3	0.64691 (15)	0.75616 (13)	0.04969 (12)	0.0305 (3)
H3	0.5748	0.7621	−0.0342	0.037*
C4	0.80703 (15)	0.77406 (13)	0.05803 (13)	0.0304 (3)
H4A	0.8449	0.7896	−0.0203	0.036*
C5	0.91044 (14)	0.76895 (12)	0.18192 (12)	0.0273 (3)
H5	1.0200	0.7824	0.1882	0.033*
C6	0.85757 (13)	0.74464 (11)	0.29708 (12)	0.0234 (2)
H6	0.9304	0.7432	0.3816	0.028*
C7	0.69174 (13)	0.63447 (11)	0.51132 (11)	0.0208 (2)
C8	0.66215 (14)	0.56772 (12)	0.71431 (12)	0.0269 (3)
H8	0.6055	0.5618	0.7825	0.032*
C9	0.79969 (15)	0.51238 (14)	0.73406 (13)	0.0321 (3)
H9	0.8393	0.4706	0.8140	0.039*
C10	0.87631 (14)	0.52129 (13)	0.63096 (13)	0.0309 (3)
H10	0.9700	0.4826	0.6402	0.037*
C11	0.27870 (12)	0.77031 (12)	0.71236 (11)	0.0219 (2)
C12	0.28250 (13)	0.64404 (12)	0.76560 (12)	0.0245 (3)
H12	0.3171	0.5728	0.7199	0.029*
C13	0.23654 (14)	0.62121 (13)	0.88390 (12)	0.0281 (3)
H13	0.2399	0.5349	0.9191	0.034*
C14	0.18554 (15)	0.72450 (14)	0.95093 (13)	0.0322 (3)
H14	0.1532	0.7093	1.0319	0.039*
C15	0.18214 (16)	0.84974 (14)	0.89877 (13)	0.0336 (3)
H15	0.1470	0.9204	0.9447	0.040*
C16	0.22895 (14)	0.87466 (12)	0.78070 (12)	0.0274 (3)
H16	0.2271	0.9617	0.7469	0.033*
C17	0.29837 (13)	0.87077 (11)	0.49672 (11)	0.0220 (2)
C18	0.34955 (14)	0.95120 (12)	0.30445 (12)	0.0277 (3)
H18	0.4052	0.9520	0.2356	0.033*
C19	0.24158 (14)	1.03965 (12)	0.30177 (12)	0.0281 (3)
H19	0.2233	1.1016	0.2342	0.034*
C20	0.16165 (14)	1.03296 (12)	0.40278 (12)	0.0271 (3)
H20	0.0840	1.0901	0.4020	0.033*

	U11	U22	U33	U12	U13	U23
N1	0.0200 (5)	0.0288 (5)	0.0229 (5)	0.0082 (4)	0.0084 (4)	0.0053 (4)
N2	0.0250 (5)	0.0245 (5)	0.0232 (5)	0.0057 (4)	0.0090 (4)	0.0032 (4)
N3	0.0237 (5)	0.0303 (5)	0.0251 (5)	0.0093 (4)	0.0068 (4)	0.0043 (4)
N4	0.0280 (5)	0.0276 (5)	0.0273 (5)	0.0120 (4)	0.0134 (4)	0.0068 (4)
N5	0.0250 (5)	0.0288 (5)	0.0260 (5)	0.0065 (4)	0.0102 (4)	0.0052 (4)
N6	0.0223 (5)	0.0262 (5)	0.0260 (5)	0.0066 (4)	0.0062 (4)	0.0031 (4)
C1	0.0246 (5)	0.0192 (5)	0.0215 (5)	0.0043 (4)	0.0086 (4)	0.0019 (4)
C2	0.0239 (6)	0.0279 (6)	0.0260 (6)	0.0052 (5)	0.0055 (5)	0.0043 (5)
C3	0.0364 (7)	0.0325 (7)	0.0221 (6)	0.0062 (5)	0.0054 (5)	0.0046 (5)
C4	0.0393 (7)	0.0294 (6)	0.0262 (6)	0.0035 (5)	0.0159 (5)	0.0041 (5)
C5	0.0273 (6)	0.0255 (6)	0.0319 (7)	0.0025 (5)	0.0140 (5)	0.0014 (5)
C6	0.0230 (5)	0.0241 (6)	0.0232 (6)	0.0032 (4)	0.0063 (4)	0.0007 (4)
C7	0.0208 (5)	0.0207 (5)	0.0206 (5)	0.0022 (4)	0.0055 (4)	−0.0003 (4)
C8	0.0319 (6)	0.0291 (6)	0.0220 (6)	0.0050 (5)	0.0107 (5)	0.0036 (5)
C9	0.0345 (7)	0.0394 (7)	0.0246 (6)	0.0114 (6)	0.0061 (5)	0.0114 (5)
C10	0.0263 (6)	0.0364 (7)	0.0317 (7)	0.0122 (5)	0.0055 (5)	0.0073 (5)
C11	0.0182 (5)	0.0257 (6)	0.0228 (6)	0.0043 (4)	0.0060 (4)	0.0035 (4)
C12	0.0245 (6)	0.0243 (6)	0.0259 (6)	0.0054 (4)	0.0080 (5)	0.0010 (5)
C13	0.0299 (6)	0.0269 (6)	0.0294 (6)	0.0042 (5)	0.0096 (5)	0.0075 (5)
C14	0.0363 (7)	0.0406 (7)	0.0259 (6)	0.0105 (6)	0.0160 (5)	0.0087 (5)
C15	0.0417 (7)	0.0368 (7)	0.0295 (7)	0.0172 (6)	0.0166 (6)	0.0036 (5)
C16	0.0328 (6)	0.0253 (6)	0.0275 (6)	0.0097 (5)	0.0104 (5)	0.0048 (5)
C17	0.0199 (5)	0.0228 (6)	0.0232 (6)	0.0025 (4)	0.0060 (4)	0.0017 (4)
C18	0.0291 (6)	0.0300 (6)	0.0254 (6)	0.0028 (5)	0.0102 (5)	0.0049 (5)
C19	0.0329 (6)	0.0254 (6)	0.0257 (6)	0.0047 (5)	0.0054 (5)	0.0074 (5)
C20	0.0268 (6)	0.0257 (6)	0.0287 (6)	0.0082 (5)	0.0042 (5)	0.0019 (5)

N1—C7	1.3613 (14)	C5—H5	0.9500
N1—C1	1.4090 (14)	C6—H6	0.9500
N1—H1	0.892 (9)	C8—C9	1.3829 (17)
N2—C8	1.3294 (15)	C8—H8	0.9500
N2—C7	1.3555 (14)	C9—C10	1.3819 (17)
N3—C10	1.3322 (15)	C9—H9	0.9500
N3—C7	1.3423 (14)	C10—H10	0.9500
N4—C17	1.3584 (15)	C11—C16	1.3950 (16)
N4—C11	1.4093 (14)	C11—C12	1.3963 (16)
N4—H4	0.894 (8)	C12—C13	1.3831 (16)
N5—C18	1.3339 (15)	C12—H12	0.9500
N5—C17	1.3570 (14)	C13—C14	1.3859 (17)
N6—C20	1.3338 (15)	C13—H13	0.9500
N6—C17	1.3407 (14)	C14—C15	1.3818 (18)
C1—C6	1.3949 (15)	C14—H14	0.9500
C1—C2	1.3958 (16)	C15—C16	1.3883 (17)
C2—C3	1.3873 (16)	C15—H15	0.9500
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.3903 (18)	C18—C19	1.3824 (17)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.3839 (18)	C19—C20	1.3824 (17)
C4—H4A	0.9500	C19—H19	0.9500
C5—C6	1.3860 (16)	C20—H20	0.9500
C7—N1—C1	128.19 (9)	C10—C9—H9	121.9
C7—N1—H1	114.6 (10)	C8—C9—H9	121.9
C1—N1—H1	117.0 (10)	N3—C10—C9	122.94 (11)
C8—N2—C7	115.61 (10)	N3—C10—H10	118.5
C10—N3—C7	116.06 (10)	C9—C10—H10	118.5
C17—N4—C11	129.13 (10)	C16—C11—C12	119.15 (10)
C17—N4—H4	115.5 (9)	C16—C11—N4	124.17 (10)
C11—N4—H4	115.4 (9)	C12—C11—N4	116.58 (10)
C18—N5—C17	115.71 (10)	C13—C12—C11	120.91 (11)
C20—N6—C17	115.97 (10)	C13—C12—H12	119.5
C6—C1—C2	119.10 (10)	C11—C12—H12	119.5
C6—C1—N1	123.56 (10)	C12—C13—C14	119.88 (11)
C2—C1—N1	117.30 (10)	C12—C13—H13	120.1
C3—C2—C1	120.70 (11)	C14—C13—H13	120.1
C3—C2—H2	119.7	C15—C14—C13	119.35 (11)
C1—C2—H2	119.7	C15—C14—H14	120.3
C2—C3—C4	120.04 (11)	C13—C14—H14	120.3
C2—C3—H3	120.0	C14—C15—C16	121.49 (11)
C4—C3—H3	120.0	C14—C15—H15	119.3
C5—C4—C3	119.13 (11)	C16—C15—H15	119.3
C5—C4—H4A	120.4	C15—C16—C11	119.20 (11)
C3—C4—H4A	120.4	C15—C16—H16	120.4
C4—C5—C6	121.39 (11)	C11—C16—H16	120.4
C4—C5—H5	119.3	N6—C17—N5	125.94 (11)
C6—C5—H5	119.3	N6—C17—N4	119.51 (10)
C5—C6—C1	119.59 (11)	N5—C17—N4	114.55 (10)
C5—C6—H6	120.2	N5—C18—C19	122.92 (11)
C1—C6—H6	120.2	N5—C18—H18	118.5
N3—C7—N2	125.92 (10)	C19—C18—H18	118.5
N3—C7—N1	119.10 (10)	C18—C19—C20	116.34 (11)
N2—C7—N1	114.96 (10)	C18—C19—H19	121.8
N2—C8—C9	123.22 (11)	C20—C19—H19	121.8
N2—C8—H8	118.4	N6—C20—C19	123.03 (11)
C9—C8—H8	118.4	N6—C20—H20	118.5
C10—C9—C8	116.22 (11)	C19—C20—H20	118.5
C7—N1—C1—C6	−31.08 (18)	C17—N4—C11—C16	−28.92 (18)
C7—N1—C1—C2	151.47 (11)	C17—N4—C11—C12	154.69 (11)
C6—C1—C2—C3	1.23 (17)	C16—C11—C12—C13	0.54 (17)
N1—C1—C2—C3	178.80 (10)	N4—C11—C12—C13	177.12 (10)
C1—C2—C3—C4	0.81 (18)	C11—C12—C13—C14	0.15 (18)
C2—C3—C4—C5	−1.85 (18)	C12—C13—C14—C15	−0.37 (19)
C3—C4—C5—C6	0.85 (18)	C13—C14—C15—C16	−0.1 (2)
C4—C5—C6—C1	1.19 (17)	C14—C15—C16—C11	0.8 (2)
C2—C1—C6—C5	−2.21 (17)	C12—C11—C16—C15	−1.00 (18)
N1—C1—C6—C5	−179.62 (10)	N4—C11—C16—C15	−177.30 (11)
C10—N3—C7—N2	−1.59 (17)	C20—N6—C17—N5	−2.37 (17)
C10—N3—C7—N1	−179.97 (10)	C20—N6—C17—N4	178.70 (10)
C8—N2—C7—N3	1.75 (16)	C18—N5—C17—N6	3.36 (17)
C8—N2—C7—N1	−179.81 (10)	C18—N5—C17—N4	−177.67 (10)
C1—N1—C7—N3	−3.22 (17)	C11—N4—C17—N6	−3.96 (18)
C1—N1—C7—N2	178.23 (10)	C11—N4—C17—N5	176.99 (11)
C7—N2—C8—C9	−0.28 (17)	C17—N5—C18—C19	−1.45 (17)
N2—C8—C9—C10	−1.14 (19)	N5—C18—C19—C20	−1.09 (18)
C7—N3—C10—C9	−0.06 (18)	C17—N6—C20—C19	−0.57 (17)
C8—C9—C10—N3	1.3 (2)	C18—C19—C20—N6	2.18 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N5	0.89 (1)	2.10 (1)	2.972 (1)	164 (1)
N4—H4···N2	0.89 (1)	2.15 (1)	3.020 (1)	165 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N5	0.89 (1)	2.10 (1)	2.972 (1)	164 (1)
N4—H4⋯N2	0.89 (1)	2.15 (1)	3.020 (1)	165 (1)