4-Amino-2-phenoxy-pyrimidine.

In the title compound, C(10)H(9)N(3)O, 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 mol-ecules 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 = 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) Å3

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

Δρmax = 0.43 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536809026580/bt2994sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026580/bt2994Isup2.hkl

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

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

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 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

	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)

	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)

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)

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)

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) .