4,6-Dichloro-5-(2-meth-oxy-phen-oxy)-2,2'-bipyrimidine.

In the title compound, C(15)H(10)Cl(2)N(4)O(2), the dichloro-pyrimidine and meth-oxy-phen-oxy parts are approximately perpendicular [dihedral angle = 89.9 (9)°]. The dihedral angle between the two pyrimidine rings is 36.3 (4)° In the crystal, there are no hydrogen bonds but the mol-ecules are held together by short inter-molecular C⋯N [3.206 (3) Å] contacts and C-H⋯π inter-actions.

Related literature

For the use of 2,2′-bipyrimidine as a ligand in inorganic and organometallic chemistry, see: Fabrice et al. (2008 ▶); Hunziker & Ludi (1977 ▶). It was first synthesized by Bly and Mellon (1962 ▶) utilizing the Ullmann coupling of 2-bromo­pyrimidine in the presence of metallic copper.

Experimental

Crystal data

C15H10Cl2N4O2

M = 349.17

Monoclinic,

a = 10.716 (2) Å

b = 8.1112 (18) Å

c = 18.601 (5) Å

β = 106.486 (3)°

V = 1550.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 296 K

0.22 × 0.20 × 0.18 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.911, T max = 0.926

8106 measured reflections

2733 independent reflections

2319 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.08

2733 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.54 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S160053681101419X/fl2331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101419X/fl2331Isup2.hkl

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

C15H10Cl2N4O2	F(000) = 712
Mr = 349.17	Dx = 1.496 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.716 (2) Å	Cell parameters from 3720 reflections
b = 8.1112 (18) Å	θ = 2.6–27.4°
c = 18.601 (5) Å	µ = 0.43 mm−1
β = 106.486 (3)°	T = 296 K
V = 1550.3 (6) Å3	Block, colourless
Z = 4	0.22 × 0.20 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	2733 independent reflections
Radiation source: fine-focus sealed tube	2319 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.911, Tmax = 0.926	k = −9→9
8106 measured reflections	l = −22→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0522P)2 + 0.7172P] where P = (Fo2 + 2Fc2)/3
2733 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl2	0.35488 (7)	0.23438 (8)	0.95225 (4)	0.0698 (2)
Cl1	−0.12322 (6)	0.00465 (9)	0.81525 (4)	0.0697 (2)
O1	0.09431 (17)	0.24803 (18)	0.84012 (8)	0.0514 (4)
N1	0.04052 (18)	−0.1321 (2)	0.93028 (10)	0.0461 (4)
O2	−0.01418 (17)	0.4733 (2)	0.74474 (9)	0.0564 (4)
N3	0.25212 (18)	−0.0303 (2)	0.99122 (9)	0.0434 (4)
N2	0.07696 (19)	−0.3406 (2)	1.05310 (10)	0.0509 (5)
C4	0.1789 (2)	−0.2855 (3)	1.03313 (11)	0.0394 (5)
C5	0.1558 (2)	−0.1388 (3)	0.98205 (11)	0.0399 (5)
N4	0.29885 (19)	−0.3461 (2)	1.05286 (11)	0.0504 (5)
C9	0.1043 (2)	0.2281 (3)	0.76750 (11)	0.0401 (5)
C8	0.1164 (2)	0.1136 (3)	0.88636 (11)	0.0437 (5)
C13	0.0568 (2)	0.3436 (3)	0.64467 (12)	0.0480 (5)
H13	0.0179	0.4242	0.6099	0.058*
C14	0.0468 (2)	0.3523 (3)	0.71727 (11)	0.0403 (5)
C12	0.1243 (2)	0.2156 (3)	0.62364 (12)	0.0512 (6)
H12	0.1311	0.2112	0.5749	0.061*
C6	0.2308 (2)	0.0942 (3)	0.94339 (11)	0.0446 (5)
C2	0.2172 (3)	−0.5496 (3)	1.11929 (13)	0.0580 (6)
H2	0.2305	−0.6438	1.1490	0.070*
C15	−0.0513 (3)	0.6175 (3)	0.69994 (17)	0.0712 (8)
H15A	−0.1114	0.5880	0.6528	0.107*
H15B	0.0245	0.6674	0.6914	0.107*
H15C	−0.0920	0.6943	0.7255	0.107*
C10	0.1703 (2)	0.1008 (3)	0.74643 (12)	0.0501 (6)
H10	0.2076	0.0185	0.7806	0.060*
C11	0.1813 (2)	0.0952 (3)	0.67400 (13)	0.0537 (6)
H11	0.2272	0.0100	0.6596	0.064*
C3	0.0986 (3)	−0.4745 (3)	1.09680 (13)	0.0564 (6)
H3	0.0303	−0.5180	1.1124	0.068*
C7	0.0238 (2)	−0.0064 (3)	0.88345 (12)	0.0457 (5)
C1	0.3157 (3)	−0.4805 (3)	1.09624 (14)	0.0589 (7)
H1	0.3978	−0.5289	1.1113	0.071*

	U11	U22	U33	U12	U13	U23
Cl2	0.0869 (5)	0.0571 (4)	0.0554 (4)	−0.0231 (3)	0.0039 (3)	0.0114 (3)
Cl1	0.0610 (4)	0.0732 (5)	0.0600 (4)	0.0094 (3)	−0.0073 (3)	0.0149 (3)
O1	0.0831 (11)	0.0397 (9)	0.0335 (8)	0.0168 (8)	0.0197 (8)	0.0094 (6)
N1	0.0521 (11)	0.0438 (10)	0.0403 (10)	0.0047 (8)	0.0095 (8)	0.0056 (8)
O2	0.0784 (11)	0.0468 (9)	0.0461 (9)	0.0198 (8)	0.0209 (8)	0.0144 (7)
N3	0.0577 (11)	0.0390 (10)	0.0316 (9)	0.0020 (8)	0.0094 (8)	0.0035 (7)
N2	0.0617 (12)	0.0495 (11)	0.0446 (10)	0.0045 (9)	0.0203 (9)	0.0101 (9)
C4	0.0534 (12)	0.0357 (11)	0.0291 (10)	0.0028 (9)	0.0115 (9)	−0.0003 (8)
C5	0.0518 (12)	0.0379 (11)	0.0307 (10)	0.0062 (9)	0.0127 (9)	0.0015 (8)
N4	0.0558 (11)	0.0447 (11)	0.0490 (11)	0.0080 (9)	0.0121 (9)	0.0089 (9)
C9	0.0471 (11)	0.0431 (12)	0.0286 (10)	−0.0003 (9)	0.0084 (8)	0.0024 (8)
C8	0.0639 (14)	0.0369 (11)	0.0313 (10)	0.0119 (10)	0.0151 (10)	0.0058 (9)
C13	0.0564 (13)	0.0493 (13)	0.0362 (11)	−0.0062 (10)	0.0095 (10)	0.0082 (10)
C14	0.0436 (11)	0.0402 (12)	0.0357 (11)	−0.0011 (9)	0.0087 (9)	0.0036 (9)
C12	0.0572 (14)	0.0628 (15)	0.0355 (12)	−0.0119 (11)	0.0164 (10)	−0.0054 (11)
C6	0.0624 (13)	0.0374 (11)	0.0334 (10)	−0.0003 (10)	0.0124 (10)	0.0003 (9)
C2	0.0844 (18)	0.0406 (13)	0.0435 (13)	0.0036 (12)	0.0093 (12)	0.0116 (10)
C15	0.0818 (19)	0.0533 (16)	0.0810 (19)	0.0250 (14)	0.0273 (15)	0.0276 (14)
C10	0.0566 (13)	0.0499 (14)	0.0410 (12)	0.0122 (11)	0.0090 (10)	0.0039 (10)
C11	0.0554 (13)	0.0608 (15)	0.0465 (13)	0.0065 (12)	0.0171 (11)	−0.0070 (11)
C3	0.0767 (17)	0.0511 (14)	0.0449 (13)	−0.0041 (12)	0.0228 (12)	0.0099 (11)
C7	0.0530 (13)	0.0463 (13)	0.0350 (11)	0.0105 (10)	0.0079 (9)	0.0040 (9)
C1	0.0678 (16)	0.0462 (14)	0.0581 (15)	0.0152 (12)	0.0103 (13)	0.0121 (11)

Cl2—C6	1.722 (2)	C8—C6	1.384 (3)
Cl1—C7	1.722 (2)	C13—C12	1.384 (3)
O1—C8	1.367 (2)	C13—C14	1.386 (3)
O1—C9	1.394 (2)	C13—H13	0.9300
N1—C7	1.320 (3)	C12—C11	1.371 (3)
N1—C5	1.335 (3)	C12—H12	0.9300
O2—C14	1.358 (3)	C2—C3	1.364 (4)
O2—C15	1.426 (3)	C2—C1	1.368 (4)
N3—C6	1.322 (3)	C2—H2	0.9300
N3—C5	1.330 (3)	C15—H15A	0.9600
N2—C4	1.327 (3)	C15—H15B	0.9600
N2—C3	1.337 (3)	C15—H15C	0.9600
C4—N4	1.328 (3)	C10—C11	1.386 (3)
C4—C5	1.498 (3)	C10—H10	0.9300
N4—C1	1.338 (3)	C11—H11	0.9300
C9—C10	1.370 (3)	C3—H3	0.9300
C9—C14	1.393 (3)	C1—H1	0.9300
C8—C7	1.380 (3)
C8—O1—C9	118.03 (16)	N3—C6—C8	123.3 (2)
C7—N1—C5	115.60 (19)	N3—C6—Cl2	117.29 (17)
C14—O2—C15	117.23 (18)	C8—C6—Cl2	119.36 (17)
C6—N3—C5	116.07 (19)	C3—C2—C1	117.1 (2)
C4—N2—C3	115.4 (2)	C3—C2—H2	121.4
N2—C4—N4	127.39 (19)	C1—C2—H2	121.4
N2—C4—C5	116.39 (19)	O2—C15—H15A	109.5
N4—C4—C5	116.22 (19)	O2—C15—H15B	109.5
N3—C5—N1	126.23 (19)	H15A—C15—H15B	109.5
N3—C5—C4	117.52 (18)	O2—C15—H15C	109.5
N1—C5—C4	116.23 (19)	H15A—C15—H15C	109.5
C4—N4—C1	115.1 (2)	H15B—C15—H15C	109.5
C10—C9—C14	121.26 (19)	C9—C10—C11	119.7 (2)
C10—C9—O1	123.52 (18)	C9—C10—H10	120.1
C14—C9—O1	115.15 (18)	C11—C10—H10	120.1
O1—C8—C7	122.9 (2)	C12—C11—C10	119.8 (2)
O1—C8—C6	122.0 (2)	C12—C11—H11	120.1
C7—C8—C6	114.86 (19)	C10—C11—H11	120.1
C12—C13—C14	120.3 (2)	N2—C3—C2	122.3 (2)
C12—C13—H13	119.9	N2—C3—H3	118.8
C14—C13—H13	119.9	C2—C3—H3	118.8
O2—C14—C13	125.57 (19)	N1—C7—C8	123.9 (2)
O2—C14—C9	116.05 (18)	N1—C7—Cl1	116.80 (18)
C13—C14—C9	118.4 (2)	C8—C7—Cl1	119.30 (16)
C11—C12—C13	120.6 (2)	N4—C1—C2	122.6 (2)
C11—C12—H12	119.7	N4—C1—H1	118.7
C13—C12—H12	119.7	C2—C1—H1	118.7

Cg is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cgi	0.93	2.87	3.760 (3)	161

Table 1

C—H⋯π interactions (Å, °)

Cg is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cgi	0.93	2.87	3.760 (3)	161

Symmetry code: (i) .