4-Amino-2-phenoxy­pyrimidine

Abstract

In the title compound, C₁₀H₉N₃O, the organic rings linked to the ether O atom make a dihedral angle of 76.8 (1)° and the C—O—C angle is widened to 119.07 (15)°. In the crystal, adjacent mol­ecules are connected by an N—H⋯N hydrogen bond, generating a chain running parallel to the b axis. The crystal is a non-merohedral twin with a ratio of twin components of 0.508 (3):0.492 (3).

Related literature

For 2-phenoxy­pyrimidine, see: Shah Bakhtiar et al. (2009 ▶). For the procedure to cope with twinned diffraction data, see: Spek (2003 ▶).

Experimental

Crystal data

• C₁₀H₉N₃O

• M _r = 187.20

• Monoclinic,

• a = 8.8443 (3) Å

• b = 12.1214 (3) Å

• c = 9.0415 (2) Å

• β = 96.751 (2)°

• V = 962.58 (5) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 120 K

• 0.40 × 0.20 × 0.10 mm

Data collection

• Bruker SMART APEX diffractometer

• Absorption correction: none

• 6375 measured reflections

• 2178 independent reflections

• 1694 reflections with I > 2σ(I)

• R _int = 0.028

Refinement

• R[F ² > 2σ(F ²)] = 0.055

• wR(F ²) = 0.163

• S = 1.10

• 2178 reflections

• 136 parameters

• 2 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.43 e Å⁻³

• Δρ_min = −0.32 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 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯N1i	0.88 (1)	2.12 (1)	2.992 (2)	173 (2)

Symmetry code: (i) .

supplementary crystallographic information

Experimental

Phenol (1.88 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) were dissolved in water (50 ml) and to the solution was added 4-amino-2-chloropyridimidine (2.60 g, 20 mmol) dissolved in THF (50 ml). The mixture was heated for 4 h. Water was added and the organic phase was extracted with chloroform. The chloroform solution was dried over sodium sulfate; slow evaporation led to the formation of colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The H atoms bonded to N were freely refined.

The crystal is a non-merohedral twin; the twin law as given by PLATON is (Spek, 2003) (-1 0 0, 0 - 1 0, 0.240 0 1); the refinement gave a ratio of twin components of 0.508 (3)/0.492 (3).

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of C10H9N3O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H9N3O	F(000) = 392
Mr = 187.20	Dx = 1.292 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2238 reflections
a = 8.8443 (3) Å	θ = 2.3–27.9°
b = 12.1214 (3) Å	µ = 0.09 mm−1
c = 9.0415 (2) Å	T = 120 K
β = 96.751 (2)°	Block, colorless
V = 962.58 (5) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer	1694 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.5°, θmin = 2.8°
ω scans	h = −10→11
6375 measured reflections	k = −15→15
2178 independent reflections	l = −10→11

Refinement

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0791P)2 + 0.3378P] where P = (Fo2 + 2Fc2)/3
2178 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.43 e Å−3
2 restraints	Δρmin = −0.32 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2422 (2)	0.48867 (12)	−0.00659 (16)	0.0317 (4)
N1	0.2790 (2)	0.36872 (13)	0.19209 (18)	0.0235 (4)
N2	0.2591 (2)	0.56448 (13)	0.21860 (17)	0.0213 (4)
N3	0.2755 (3)	0.64646 (15)	0.4479 (2)	0.0348 (5)
H1	0.252 (3)	0.7092 (13)	0.402 (2)	0.030 (7)*
H2	0.284 (3)	0.641 (2)	0.5458 (11)	0.037 (7)*
C1	0.2551 (3)	0.39941 (16)	−0.1029 (2)	0.0220 (5)
C2	0.3964 (3)	0.35937 (18)	−0.1237 (2)	0.0264 (5)
H2A	0.4857	0.3889	−0.0693	0.032*
C3	0.4063 (3)	0.27495 (19)	−0.2257 (2)	0.0339 (6)
H3	0.5030	0.2460	−0.2410	0.041*
C4	0.2763 (4)	0.23278 (18)	−0.3052 (2)	0.0369 (7)
H4	0.2836	0.1744	−0.3741	0.044*
C5	0.1354 (3)	0.2756 (2)	−0.2843 (2)	0.0374 (6)
H5	0.0461	0.2475	−0.3403	0.045*
C6	0.1240 (3)	0.35942 (19)	−0.1819 (2)	0.0307 (5)
H6	0.0274	0.3887	−0.1665	0.037*
C7	0.2617 (2)	0.47102 (16)	0.1428 (2)	0.0197 (4)
C8	0.2997 (3)	0.36125 (17)	0.3429 (2)	0.0283 (5)
H8	0.3133	0.2900	0.3862	0.034*
C9	0.3022 (3)	0.44951 (17)	0.4354 (2)	0.0296 (5)
H9	0.3190	0.4413	0.5405	0.036*
C10	0.2785 (3)	0.55438 (16)	0.3677 (2)	0.0236 (5)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0606 (12)	0.0159 (7)	0.0178 (7)	0.0050 (7)	0.0018 (7)	0.0013 (5)
N1	0.0341 (11)	0.0165 (8)	0.0197 (8)	0.0014 (7)	0.0032 (7)	0.0007 (6)
N2	0.0281 (10)	0.0149 (8)	0.0212 (8)	0.0028 (7)	0.0038 (7)	0.0003 (6)
N3	0.0665 (16)	0.0182 (9)	0.0204 (9)	0.0070 (9)	0.0083 (9)	−0.0008 (7)
C1	0.0351 (13)	0.0156 (9)	0.0151 (9)	0.0006 (8)	0.0018 (8)	0.0031 (7)
C2	0.0301 (12)	0.0255 (10)	0.0229 (10)	−0.0038 (9)	0.0005 (9)	0.0044 (8)
C3	0.0476 (15)	0.0264 (11)	0.0310 (11)	0.0084 (11)	0.0186 (11)	0.0062 (9)
C4	0.073 (2)	0.0193 (10)	0.0198 (10)	−0.0061 (12)	0.0127 (11)	−0.0026 (8)
C5	0.0511 (17)	0.0348 (12)	0.0238 (11)	−0.0161 (12)	−0.0058 (11)	0.0001 (9)
C6	0.0311 (13)	0.0319 (12)	0.0284 (11)	0.0006 (10)	0.0013 (10)	0.0036 (9)
C7	0.0217 (11)	0.0186 (9)	0.0185 (9)	0.0015 (8)	0.0012 (8)	0.0019 (7)
C8	0.0455 (14)	0.0174 (9)	0.0221 (10)	0.0044 (9)	0.0046 (9)	0.0046 (7)
C9	0.0482 (15)	0.0216 (10)	0.0194 (9)	0.0028 (10)	0.0057 (9)	0.0027 (7)
C10	0.0312 (12)	0.0181 (9)	0.0223 (9)	0.0008 (8)	0.0062 (9)	−0.0007 (7)

Geometric parameters (Å, °)

O1—C7	1.359 (2)	C2—H2A	0.9500
O1—C1	1.402 (2)	C3—C4	1.380 (4)
N1—C7	1.320 (2)	C3—H3	0.9500
N1—C8	1.357 (3)	C4—C5	1.384 (4)
N2—C7	1.326 (2)	C4—H4	0.9500
N2—C10	1.344 (2)	C5—C6	1.386 (3)
N3—C10	1.333 (3)	C5—H5	0.9500
N3—H1	0.880 (10)	C6—H6	0.9500
N3—H2	0.882 (10)	C8—C9	1.356 (3)
C1—C2	1.375 (3)	C8—H8	0.9500
C1—C6	1.376 (3)	C9—C10	1.416 (3)
C2—C3	1.387 (3)	C9—H9	0.9500
C7—O1—C1	119.07 (15)	C4—C5—C6	120.2 (2)
C7—N1—C8	113.46 (17)	C4—C5—H5	119.9
C7—N2—C10	115.63 (16)	C6—C5—H5	119.9
C10—N3—H1	119.1 (16)	C1—C6—C5	118.8 (2)
C10—N3—H2	118.5 (18)	C1—C6—H6	120.6
H1—N3—H2	122 (2)	C5—C6—H6	120.6
C2—C1—C6	121.9 (2)	N1—C7—N2	129.54 (18)
C2—C1—O1	120.0 (2)	N1—C7—O1	118.65 (17)
C6—C1—O1	118.0 (2)	N2—C7—O1	111.80 (16)
C1—C2—C3	118.7 (2)	C9—C8—N1	123.86 (18)
C1—C2—H2A	120.6	C9—C8—H8	118.1
C3—C2—H2A	120.6	N1—C8—H8	118.1
C4—C3—C2	120.4 (2)	C8—C9—C10	116.79 (18)
C4—C3—H3	119.8	C8—C9—H9	121.6
C2—C3—H3	119.8	C10—C9—H9	121.6
C3—C4—C5	119.9 (2)	N3—C10—N2	117.46 (18)
C3—C4—H4	120.0	N3—C10—C9	121.85 (18)
C5—C4—H4	120.0	N2—C10—C9	120.69 (18)
C7—O1—C1—C2	−76.8 (2)	C8—N1—C7—O1	179.1 (2)
C7—O1—C1—C6	107.6 (2)	C10—N2—C7—N1	0.8 (3)
C6—C1—C2—C3	−1.1 (3)	C10—N2—C7—O1	−179.63 (19)
O1—C1—C2—C3	−176.53 (17)	C1—O1—C7—N1	−5.8 (3)
C1—C2—C3—C4	0.4 (3)	C1—O1—C7—N2	174.56 (18)
C2—C3—C4—C5	0.7 (3)	C7—N1—C8—C9	0.2 (4)
C3—C4—C5—C6	−1.2 (3)	N1—C8—C9—C10	1.3 (4)
C2—C1—C6—C5	0.6 (3)	C7—N2—C10—N3	−179.5 (2)
O1—C1—C6—C5	176.15 (18)	C7—N2—C10—C9	0.9 (3)
C4—C5—C6—C1	0.5 (3)	C8—C9—C10—N3	178.6 (2)
C8—N1—C7—N2	−1.3 (3)	C8—C9—C10—N2	−1.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···N1i	0.88 (1)	2.12 (1)	2.992 (2)	173 (2)

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2.