N-(Pyrimidin-2-yl)aniline

Badaruddin, E.; Shah Bakhtiar, N.; Aiyub, Z.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809007685

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o703

doi:10.1107/S1600536809007685

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N-(Pyrimidin-2-yl)aniline

Edura Badaruddin,^a Nasir Shah Bakhtiar,^a Zaharah Aiyub,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 March 2009; accepted 3 March 2009; online 6 March 2009)

There are two molecules in the asymmetric unit of the title compound, C₁₀H₉N₃, 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 molecules 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_r = 171.20
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.03
3950 reflections
243 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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)

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 ).

Supporting information

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

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

checkCIF report

Related literature top

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

Experimental top

2-Chloropyrimidine (0.05 mol), aniline (0.05 mol) and ethanol (5 ml) were heated at 423–433 K for 3 h. The product was dissolved in water and the solution extracted with ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped colorless crystals along with some unidentified brown material.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₀H₉N₃ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Dashed lines denote hydrogen bonds.

N-(Pyrimidin-2-yl)aniline top

Crystal data top

C₁₀H₉N₃	Z = 4
M_r = 171.20	F(000) = 360
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.056P)² + 0.1316P] where P = (F_o² + 2F_c²)/3
3950 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₉N₃	γ = 97.780 (1)°
M_r = 171.20	V = 863.28 (3) Å³
Triclinic, P1	Z = 4
a = 8.8792 (2) Å	Mo Kα radiation
b = 9.9382 (2) Å	µ = 0.08 mm⁻¹
c = 10.2038 (2) Å	T = 123 K
α = 93.186 (1)°	0.35 × 0.20 × 0.10 mm
β = 103.665 (1)°

Data collection top

Bruker SMART APEX diffractometer	3144 reflections with I > 2σ(I)
8238 measured reflections	R_int = 0.020
3950 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
3950 reflections	Δρ_min = −0.23 e Å⁻³
243 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₃
M_r	171.20
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	8.8792 (2), 9.9382 (2), 10.2038 (2)
α, β, γ (°)	93.186 (1), 103.665 (1), 97.780 (1)
V (Å³)	863.28 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8238, 3950, 3144
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.03
No. of reflections	3950
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

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)

Acknowledgements

The authors thank the University of Malaya for supporting this study.

References

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