3-Nitro­phenyl pyrimidin-2-yl ether

Shah Bakhtiar, N.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809007697

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o704

doi:10.1107/S1600536809007697

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3-Nitrophenyl pyrimidin-2-yl ether

Nasir Shah Bakhtiar,^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)

In the title compound, C₁₀H₇N₃O₃, 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_r = 217.19
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.02
2242 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007697/hb2922sup1.cif

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

checkCIF report

Related literature top

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

Experimental top

3-Nitrophenol (2.78 g, 20 mmol) was mixed with sodium hydroxide (0.08 g, 20 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-chloropyrimidine (2.30 g, 20 mmol) at 423–433 K for 6 h. The product was dissolved in water and the solution extracted with chloroform. The chloroform phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped very pale brown blocks of (I) 40% yield along with some unidentified brown material.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. The molecular structure of (I) with displacement ellipsoids drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

3-Nitrophenyl pyrimidin-2-yl ether top

Crystal data top

C₁₀H₇N₃O₃	F(000) = 896
M_r = 217.19	D_x = 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

Data collection top

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

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0556P)² + 0.7122P] where P = (F_o² + 2F_c²)/3
2242 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₀H₇N₃O₃	V = 1942.15 (6) Å³
M_r = 217.19	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 18.1360 (3) Å	µ = 0.11 mm⁻¹
b = 7.3355 (1) Å	T = 118 K
c = 14.5986 (3) Å	0.40 × 0.20 × 0.15 mm

Data collection top

Bruker SMART APEX CCD diffractometer	1890 reflections with I > 2σ(I)
12785 measured reflections	R_int = 0.029
2242 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.02	Δρ_max = 0.27 e Å⁻³
2242 reflections	Δρ_min = −0.29 e Å⁻³
145 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₇N₃O₃
M_r	217.19
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	118
a, b, c (Å)	18.1360 (3), 7.3355 (1), 14.5986 (3)
V (Å³)	1942.15 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12785, 2242, 1890
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.02
No. of reflections	2242
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank the University of Malaya for supporting this study (FS358/2008 A).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Westrip, S. P. (2009). publCIF. In preparation. Google Scholar