3-Nitro-phenyl pyrimidin-2-yl ether.

In the title compound, C(10)H(7)N(3)O(3), the dihedral angle between the two aromatic rings is 87.5 (1) Å; their ipso-C atoms subtend an angle of 117.4 (1)° at the ether O atom.

Related literature

For the structure of phenyl pyrimidin-2-yl ether, see: Shah Bakhtiar et al. (2009 ▶).

Experimental

Crystal data

C10H7N3O3

M = 217.19

Orthorhombic,

a = 18.1360 (3) Å

b = 7.3355 (1) Å

c = 14.5986 (3) Å

V = 1942.15 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 118 K

0.40 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: none

12785 measured reflections

2242 independent reflections

1890 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.02

2242 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536809007697/hb2922sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007697/hb2922Isup2.hkl

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

C10H7N3O3	F(000) = 896
Mr = 217.19	Dx = 1.486 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4130 reflections
a = 18.1360 (3) Å	θ = 2.8–28.2°
b = 7.3355 (1) Å	µ = 0.11 mm−1
c = 14.5986 (3) Å	T = 118 K
V = 1942.15 (6) Å3	Block, faint brown
Z = 8	0.40 × 0.20 × 0.15 mm

Bruker SMART APEX CCD diffractometer	1890 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 27.5°, θmin = 2.3°
ω scans	h = −23→23
12785 measured reflections	k = −9→9
2242 independent reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0556P)2 + 0.7122P] where P = (Fo2 + 2Fc2)/3
2242 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.46423 (5)	0.52259 (12)	0.36904 (6)	0.0222 (2)
O2	0.34305 (5)	0.73218 (14)	0.08352 (6)	0.0291 (2)
O3	0.22956 (6)	0.7828 (2)	0.12079 (7)	0.0467 (3)
N1	0.42087 (6)	0.22878 (14)	0.35641 (8)	0.0228 (2)
N2	0.54579 (6)	0.29874 (15)	0.39501 (8)	0.0234 (3)
N3	0.29278 (6)	0.73707 (16)	0.13953 (7)	0.0238 (3)
C1	0.43734 (8)	0.05109 (18)	0.36142 (10)	0.0280 (3)
H1	0.3994	−0.0355	0.3502	0.034*
C2	0.50707 (8)	−0.01134 (18)	0.38219 (10)	0.0284 (3)
H2	0.5182	−0.1378	0.3850	0.034*
C3	0.56002 (7)	0.12058 (19)	0.39866 (10)	0.0267 (3)
H3	0.6087	0.0824	0.4132	0.032*
C4	0.47660 (7)	0.33980 (16)	0.37377 (8)	0.0180 (3)
C5	0.39288 (6)	0.58007 (15)	0.34572 (8)	0.0179 (3)
C6	0.34150 (7)	0.60883 (16)	0.41443 (8)	0.0205 (3)
H6	0.3532	0.5820	0.4764	0.025*
C7	0.27269 (7)	0.67742 (17)	0.39132 (9)	0.0218 (3)
H7	0.2369	0.6965	0.4378	0.026*
C8	0.25564 (7)	0.71852 (17)	0.30078 (8)	0.0202 (3)
H8	0.2086	0.7655	0.2845	0.024*
C9	0.30919 (7)	0.68896 (16)	0.23527 (8)	0.0181 (3)
C10	0.37846 (6)	0.61910 (15)	0.25487 (8)	0.0180 (2)
H10	0.4141	0.5991	0.2083	0.022*

	U11	U22	U33	U12	U13	U23
O1	0.0150 (4)	0.0171 (4)	0.0344 (5)	−0.0013 (3)	−0.0053 (4)	0.0031 (4)
O2	0.0272 (5)	0.0406 (6)	0.0196 (5)	−0.0023 (4)	0.0039 (4)	0.0012 (4)
O3	0.0262 (6)	0.0873 (10)	0.0266 (6)	0.0152 (6)	−0.0062 (4)	0.0083 (6)
N1	0.0197 (5)	0.0192 (5)	0.0295 (6)	−0.0015 (4)	−0.0035 (4)	−0.0006 (4)
N2	0.0175 (5)	0.0233 (6)	0.0294 (6)	0.0008 (4)	−0.0015 (4)	0.0036 (4)
N3	0.0215 (5)	0.0300 (6)	0.0199 (5)	0.0000 (4)	−0.0019 (4)	0.0000 (4)
C1	0.0278 (7)	0.0187 (6)	0.0375 (8)	−0.0030 (5)	−0.0046 (6)	−0.0024 (5)
C2	0.0300 (7)	0.0199 (6)	0.0352 (7)	0.0038 (5)	−0.0011 (6)	−0.0005 (5)
C3	0.0209 (6)	0.0265 (7)	0.0326 (7)	0.0050 (5)	−0.0013 (5)	0.0033 (5)
C4	0.0183 (6)	0.0186 (6)	0.0173 (6)	−0.0010 (4)	0.0003 (4)	0.0019 (4)
C5	0.0150 (5)	0.0133 (5)	0.0255 (6)	−0.0016 (4)	−0.0025 (5)	0.0005 (4)
C6	0.0237 (6)	0.0193 (6)	0.0186 (6)	−0.0031 (5)	−0.0010 (5)	0.0015 (4)
C7	0.0215 (6)	0.0224 (6)	0.0214 (6)	0.0007 (5)	0.0046 (5)	−0.0013 (5)
C8	0.0154 (5)	0.0213 (6)	0.0240 (6)	0.0022 (4)	0.0007 (5)	−0.0010 (5)
C9	0.0185 (6)	0.0182 (5)	0.0175 (6)	−0.0013 (4)	−0.0012 (4)	−0.0005 (4)
C10	0.0152 (5)	0.0173 (5)	0.0214 (6)	−0.0010 (4)	0.0023 (4)	−0.0021 (4)

O1—C4	1.3613 (15)	C2—H2	0.9500
O1—C5	1.4029 (14)	C3—H3	0.9500
O2—N3	1.2252 (14)	C5—C10	1.3819 (17)
O3—N3	1.2256 (15)	C5—C6	1.3852 (17)
N1—C4	1.3225 (16)	C6—C7	1.3872 (18)
N1—C1	1.3392 (17)	C6—H6	0.9500
N2—C4	1.3273 (16)	C7—C8	1.3907 (18)
N2—C3	1.3332 (17)	C7—H7	0.9500
N3—C9	1.4720 (16)	C8—C9	1.3801 (17)
C1—C2	1.379 (2)	C8—H8	0.9500
C1—H1	0.9500	C9—C10	1.3867 (17)
C2—C3	1.384 (2)	C10—H10	0.9500
C4—O1—C5	117.41 (9)	C10—C5—C6	122.42 (11)
C4—N1—C1	114.73 (11)	C10—C5—O1	118.01 (10)
C4—N2—C3	114.50 (11)	C6—C5—O1	119.37 (11)
O2—N3—O3	123.73 (11)	C5—C6—C7	118.97 (11)
O2—N3—C9	118.44 (11)	C5—C6—H6	120.5
O3—N3—C9	117.82 (11)	C7—C6—H6	120.5
N1—C1—C2	122.68 (13)	C6—C7—C8	120.65 (11)
N1—C1—H1	118.7	C6—C7—H7	119.7
C2—C1—H1	118.7	C8—C7—H7	119.7
C1—C2—C3	116.25 (12)	C9—C8—C7	117.91 (11)
C1—C2—H2	121.9	C9—C8—H8	121.0
C3—C2—H2	121.9	C7—C8—H8	121.0
N2—C3—C2	122.96 (12)	C8—C9—C10	123.55 (11)
N2—C3—H3	118.5	C8—C9—N3	118.55 (11)
C2—C3—H3	118.5	C10—C9—N3	117.88 (11)
N1—C4—N2	128.87 (12)	C5—C10—C9	116.49 (11)
N1—C4—O1	118.10 (11)	C5—C10—H10	121.8
N2—C4—O1	113.03 (10)	C9—C10—H10	121.8
C4—N1—C1—C2	−0.6 (2)	O1—C5—C6—C7	175.68 (10)
N1—C1—C2—C3	0.5 (2)	C5—C6—C7—C8	−0.65 (18)
C4—N2—C3—C2	−0.3 (2)	C6—C7—C8—C9	−0.02 (18)
C1—C2—C3—N2	0.0 (2)	C7—C8—C9—C10	0.66 (18)
C1—N1—C4—N2	0.2 (2)	C7—C8—C9—N3	−178.15 (11)
C1—N1—C4—O1	179.32 (11)	O2—N3—C9—C8	171.09 (11)
C3—N2—C4—N1	0.3 (2)	O3—N3—C9—C8	−7.71 (18)
C3—N2—C4—O1	−178.92 (11)	O2—N3—C9—C10	−7.78 (17)
C5—O1—C4—N1	−0.16 (16)	O3—N3—C9—C10	173.41 (13)
C5—O1—C4—N2	179.13 (10)	C6—C5—C10—C9	−0.15 (17)
C4—O1—C5—C10	−94.96 (13)	O1—C5—C10—C9	−175.15 (10)
C4—O1—C5—C6	89.88 (13)	C8—C9—C10—C5	−0.57 (18)
C10—C5—C6—C7	0.74 (18)	N3—C9—C10—C5	178.25 (10)