2-[4-(Chloro-meth-yl)phen-oxy]-4,6-dimeth-oxy-pyrimidine.

The title compound, C(13)H(13)ClN(2)O(3), was synthesized in the course of the search for novel bioactive pyrimidine derivatives. The C-O-C angle at the phen-oxy O atom is widened to 119.87 (18)°. The dihedral angle between the pyrimidine and benzene rings is 64.2 (3)°.

Related literature

For the biological activity of pyrimidine derivatives, see: Amin et al. (2011 ▶); Chen et al. (2009 ▶); Popova et al. (1999 ▶); Sagi et al. (2011 ▶); Stec et al. (2008 ▶). For related structures of 2-phen­oxy­pyrimidines, see: Shah Bakhtiar et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H13ClN2O3

M = 280.70

Monoclinic,

a = 8.3998 (17) Å

b = 23.145 (5) Å

c = 7.7967 (16) Å

β = 117.28 (3)°

V = 1347.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 113 K

0.30 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.912, T max = 0.942

11307 measured reflections

2358 independent reflections

1899 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.134

S = 1.09

2358 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026220/yk2059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026220/yk2059Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026220/yk2059Isup3.cml

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

C13H13ClN2O3	F(000) = 584
Mr = 280.70	Dx = 1.384 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11126 reflections
a = 8.3998 (17) Å	θ = 3.1–27.6°
b = 23.145 (5) Å	µ = 0.29 mm−1
c = 7.7967 (16) Å	T = 113 K
β = 117.28 (3)°	Prism, colourless
V = 1347.2 (6) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2358 independent reflections
Radiation source: fine-focus sealed tube	1899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 14.22 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω and φ scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −27→27
Tmin = 0.912, Tmax = 0.942	l = −9→9
11307 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.8134P] where P = (Fo2 + 2Fc2)/3
2358 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	1.0641 (3)	0.96956 (10)	0.2361 (4)	0.0471 (6)
C2	1.2474 (3)	0.97248 (11)	0.3080 (4)	0.0517 (6)
H2	1.3138	1.0040	0.3785	0.062*
C3	1.3259 (3)	0.92547 (10)	0.2683 (3)	0.0446 (6)
C4	1.5903 (4)	0.87913 (13)	0.2908 (5)	0.0638 (8)
H4A	1.5472	0.8434	0.3166	0.096*
H4B	1.7177	0.8815	0.3689	0.096*
H4C	1.5624	0.8807	0.1569	0.096*
C5	0.7922 (4)	1.01267 (13)	0.2028 (5)	0.0692 (8)
H5A	0.7339	0.9971	0.0744	0.104*
H5B	0.7470	1.0507	0.2032	0.104*
H5C	0.7689	0.9882	0.2882	0.104*
C6	1.0600 (3)	0.88216 (10)	0.1124 (3)	0.0437 (6)
C7	0.7881 (3)	0.82754 (10)	−0.0485 (4)	0.0454 (6)
C8	0.7325 (3)	0.78267 (11)	0.0275 (4)	0.0524 (6)
H8	0.8158	0.7593	0.1241	0.063*
C9	0.5507 (4)	0.77293 (11)	−0.0426 (4)	0.0509 (6)
H9	0.5123	0.7425	0.0072	0.061*
C10	0.4246 (3)	0.80752 (11)	−0.1854 (3)	0.0448 (6)
C11	0.4845 (3)	0.85228 (11)	−0.2603 (4)	0.0507 (6)
H11	0.4017	0.8758	−0.3565	0.061*
C12	0.6662 (4)	0.86220 (11)	−0.1929 (4)	0.0520 (6)
H12	0.7054	0.8919	−0.2446	0.062*
C13	0.2290 (4)	0.79504 (14)	−0.2462 (4)	0.0653 (8)
H13A	0.2013	0.8076	−0.1442	0.078*
H13B	0.2104	0.7536	−0.2602	0.078*
Cl1	0.07844 (11)	0.82848 (5)	−0.46320 (16)	0.1037 (4)
N1	0.9659 (3)	0.92397 (8)	0.1384 (3)	0.0452 (5)
N2	1.2352 (2)	0.87930 (9)	0.1678 (3)	0.0450 (5)
O1	0.9816 (3)	1.01557 (8)	0.2666 (3)	0.0647 (6)
O2	1.5055 (2)	0.92689 (8)	0.3357 (3)	0.0565 (5)
O3	0.9740 (2)	0.83341 (7)	0.0165 (3)	0.0576 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0597 (15)	0.0372 (13)	0.0493 (14)	0.0004 (11)	0.0293 (13)	−0.0034 (11)
C2	0.0567 (15)	0.0407 (14)	0.0558 (15)	−0.0089 (11)	0.0242 (13)	−0.0105 (12)
C3	0.0450 (13)	0.0441 (14)	0.0448 (14)	−0.0059 (11)	0.0206 (11)	−0.0004 (11)
C4	0.0492 (15)	0.0636 (18)	0.079 (2)	0.0021 (13)	0.0293 (15)	−0.0057 (15)
C5	0.073 (2)	0.0577 (18)	0.091 (2)	0.0119 (15)	0.0504 (18)	−0.0029 (16)
C6	0.0476 (13)	0.0373 (13)	0.0476 (14)	−0.0038 (10)	0.0232 (11)	−0.0047 (10)
C7	0.0420 (12)	0.0390 (13)	0.0553 (15)	−0.0055 (10)	0.0223 (11)	−0.0138 (11)
C8	0.0535 (15)	0.0410 (14)	0.0590 (16)	0.0046 (11)	0.0227 (13)	0.0017 (12)
C9	0.0594 (15)	0.0390 (14)	0.0620 (16)	−0.0044 (11)	0.0345 (14)	0.0017 (12)
C10	0.0468 (13)	0.0457 (14)	0.0438 (13)	−0.0065 (11)	0.0224 (11)	−0.0096 (11)
C11	0.0515 (14)	0.0496 (15)	0.0443 (14)	−0.0016 (11)	0.0163 (12)	0.0027 (11)
C12	0.0577 (15)	0.0454 (15)	0.0546 (15)	−0.0115 (12)	0.0271 (13)	−0.0012 (12)
C13	0.0529 (16)	0.077 (2)	0.0670 (18)	−0.0118 (14)	0.0280 (14)	−0.0035 (16)
Cl1	0.0508 (5)	0.1230 (9)	0.1064 (8)	−0.0071 (5)	0.0095 (5)	0.0305 (6)
N1	0.0478 (11)	0.0396 (11)	0.0497 (12)	0.0002 (9)	0.0236 (10)	−0.0043 (9)
N2	0.0444 (11)	0.0408 (11)	0.0518 (12)	−0.0035 (9)	0.0238 (10)	−0.0049 (9)
O1	0.0698 (12)	0.0451 (11)	0.0882 (15)	0.0026 (9)	0.0442 (11)	−0.0150 (10)
O2	0.0443 (9)	0.0555 (11)	0.0666 (12)	−0.0082 (8)	0.0227 (9)	−0.0125 (9)
O3	0.0451 (10)	0.0445 (10)	0.0826 (13)	−0.0061 (8)	0.0288 (9)	−0.0208 (9)

C1—N1	1.341 (3)	C6—O3	1.363 (3)
C1—O1	1.350 (3)	C7—C12	1.379 (4)
C1—C2	1.378 (4)	C7—C8	1.378 (4)
C2—C3	1.379 (3)	C7—O3	1.410 (3)
C2—H2	0.9300	C8—C9	1.385 (4)
C3—N2	1.337 (3)	C8—H8	0.9300
C3—O2	1.351 (3)	C9—C10	1.386 (4)
C4—O2	1.442 (3)	C9—H9	0.9300
C4—H4A	0.9600	C10—C11	1.391 (3)
C4—H4B	0.9600	C10—C13	1.514 (3)
C4—H4C	0.9600	C11—C12	1.387 (4)
C5—O1	1.435 (3)	C11—H11	0.9300
C5—H5A	0.9600	C12—H12	0.9300
C5—H5B	0.9600	C13—Cl1	1.760 (3)
C5—H5C	0.9600	C13—H13A	0.9700
C6—N1	1.322 (3)	C13—H13B	0.9700
C6—N2	1.332 (3)
N1—C1—O1	119.3 (2)	C7—C8—C9	118.8 (2)
N1—C1—C2	123.4 (2)	C7—C8—H8	120.6
O1—C1—C2	117.2 (2)	C9—C8—H8	120.6
C1—C2—C3	115.5 (2)	C8—C9—C10	121.4 (2)
C1—C2—H2	122.3	C8—C9—H9	119.3
C3—C2—H2	122.3	C10—C9—H9	119.3
N2—C3—O2	118.8 (2)	C9—C10—C11	118.5 (2)
N2—C3—C2	124.0 (2)	C9—C10—C13	117.5 (2)
O2—C3—C2	117.2 (2)	C11—C10—C13	124.0 (2)
O2—C4—H4A	109.5	C12—C11—C10	120.7 (2)
O2—C4—H4B	109.5	C12—C11—H11	119.6
H4A—C4—H4B	109.5	C10—C11—H11	119.6
O2—C4—H4C	109.5	C7—C12—C11	119.3 (2)
H4A—C4—H4C	109.5	C7—C12—H12	120.4
H4B—C4—H4C	109.5	C11—C12—H12	120.4
O1—C5—H5A	109.5	C10—C13—Cl1	114.6 (2)
O1—C5—H5B	109.5	C10—C13—H13A	108.6
H5A—C5—H5B	109.5	Cl1—C13—H13A	108.6
O1—C5—H5C	109.5	C10—C13—H13B	108.6
H5A—C5—H5C	109.5	Cl1—C13—H13B	108.6
H5B—C5—H5C	109.5	H13A—C13—H13B	107.6
N1—C6—N2	129.5 (2)	C6—N1—C1	114.1 (2)
N1—C6—O3	119.1 (2)	C6—N2—C3	113.5 (2)
N2—C6—O3	111.5 (2)	C1—O1—C5	118.6 (2)
C12—C7—C8	121.2 (2)	C3—O2—C4	118.3 (2)
C12—C7—O3	121.5 (2)	C6—O3—C7	119.87 (18)
C8—C7—O3	117.1 (2)