Methyl 2,6-bis-[(5-bromo-4,6-dimeth-oxy-pyrimidin-2-yl)-oxy]benzoate.

In the title compound, C(20)H(18)Br(2)N(4)O(8), the inter-planar angle of the pyrimidine rings is 75.1 (2)°. The central benzene ring is inclined at inter-planar angles of 66.5 (2) and 71.9 (2)° with respect to the two pyrimidine rings. In the crystal structure, adjacent mol-ecules are connected into two-mol-ecule-thick arrays parallel to the bc plane via short Br⋯Br [3.5328 (12) Å] and Br⋯O [3.206 (3) and 3.301 (4) Å] inter-actions. A weak inter-molecular π-π aromatic stacking inter-action [centroid-centroid distance = 3.526 (3) Å] is also observed.

Related literature

For general background to and applications of the title compound, see: Koichiro et al. (1988 ▶); He et al. (2007 ▶); Li et al. (2006 ▶); Gerorge (1983 ▶). For closely related structures, see: Fun et al. (2010 ▶); Li & Luo (2006 ▶).

Experimental

Crystal data

C20H18Br2N4O8

M = 602.20

Monoclinic,

a = 29.972 (5) Å

b = 8.1392 (12) Å

c = 23.061 (3) Å

β = 123.120 (3)°

V = 4711.8 (12) Å3

Z = 8

Mo Kα radiation

μ = 3.49 mm−1

T = 293 K

0.20 × 0.18 × 0.14 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.549, T max = 0.640

25204 measured reflections

8438 independent reflections

4458 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.254

S = 1.02

8438 reflections

306 parameters

H-atom parameters constrained

Δρmax = 1.32 e Å−3

Δρmin = −1.56 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024724/hb5519sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024724/hb5519Isup2.hkl

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

C20H18Br2N4O8	F(000) = 2400
Mr = 602.20	Dx = 1.698 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2909 reflections
a = 29.972 (5) Å	θ = 2.7–25.5°
b = 8.1392 (12) Å	µ = 3.49 mm−1
c = 23.061 (3) Å	T = 293 K
β = 123.120 (3)°	Block, brown
V = 4711.8 (12) Å3	0.20 × 0.18 × 0.14 mm
Z = 8

Bruker APEXII DUO CCD diffractometer	8438 independent reflections
Radiation source: fine-focus sealed tube	4458 reflections with I > 2σ(I)
graphite	Rint = 0.066
φ and ω scans	θmax = 32.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −45→45
Tmin = 0.549, Tmax = 0.640	k = −12→12
25204 measured reflections	l = −34→34

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.254	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1449P)2] where P = (Fo2 + 2Fc2)/3
8438 reflections	(Δ/σ)max = 0.001
306 parameters	Δρmax = 1.32 e Å−3
0 restraints	Δρmin = −1.55 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
Br1	0.30639 (2)	0.57188 (7)	0.09822 (4)	0.0594 (2)
Br2	0.08330 (2)	0.91910 (6)	0.40182 (3)	0.04252 (17)
O1	0.11548 (12)	0.9112 (3)	0.04513 (18)	0.0337 (7)
O2	0.05069 (15)	0.5753 (3)	0.15875 (19)	0.0372 (7)
O3	0.28301 (15)	0.9322 (4)	0.0904 (3)	0.0563 (11)
O4	0.20456 (14)	0.4280 (4)	0.0769 (2)	0.0459 (9)
O5	0.16295 (15)	0.8884 (5)	0.1855 (2)	0.0568 (10)
O6	0.16019 (17)	0.6258 (6)	0.2086 (3)	0.0729 (14)
O7	0.07542 (16)	0.5580 (4)	0.3707 (2)	0.0422 (8)
O8	0.06803 (15)	1.0608 (4)	0.27029 (19)	0.0409 (8)
N1	0.19889 (16)	0.9262 (4)	0.0691 (2)	0.0377 (9)
N2	0.15798 (13)	0.6659 (4)	0.0595 (2)	0.0324 (8)
N3	0.06285 (16)	0.5635 (4)	0.2625 (2)	0.0334 (8)
N4	0.05992 (14)	0.8206 (4)	0.21251 (19)	0.0320 (7)
C1	0.24118 (18)	0.8474 (6)	0.0787 (3)	0.0378 (10)
C2	0.24567 (18)	0.6781 (6)	0.0836 (3)	0.0389 (10)
C3	0.20209 (17)	0.5919 (5)	0.0728 (3)	0.0352 (9)
C4	0.15971 (16)	0.8269 (5)	0.0587 (2)	0.0311 (9)
C5	0.07637 (16)	0.8238 (5)	0.0466 (2)	0.0314 (9)
C6	0.02573 (18)	0.8241 (6)	−0.0133 (3)	0.0410 (11)
H6A	0.0198	0.8777	−0.0526	0.049*
C7	−0.01538 (19)	0.7465 (6)	−0.0153 (3)	0.0472 (12)
H7A	−0.0494	0.7494	−0.0554	0.057*
C8	−0.00662 (19)	0.6642 (6)	0.0420 (3)	0.0410 (11)
H8A	−0.0343	0.6082	0.0405	0.049*
C9	0.04382 (18)	0.6656 (5)	0.1021 (2)	0.0337 (9)
C10	0.08581 (17)	0.7468 (5)	0.1067 (2)	0.0314 (8)
C11	0.05805 (17)	0.6583 (5)	0.2136 (2)	0.0310 (8)
C12	0.06957 (17)	0.6433 (5)	0.3175 (2)	0.0315 (8)
C13	0.07150 (16)	0.8121 (5)	0.3220 (2)	0.0318 (9)
C14	0.06590 (16)	0.8963 (5)	0.2677 (2)	0.0300 (8)
C15	0.2797 (3)	1.1092 (7)	0.0878 (5)	0.068 (2)
H15A	0.3105	1.1541	0.0909	0.101*
H15B	0.2780	1.1486	0.1259	0.101*
H15C	0.2482	1.1428	0.0450	0.101*
C16	0.1604 (2)	0.3438 (6)	0.0691 (4)	0.0586 (17)
H16A	0.1653	0.2277	0.0675	0.088*
H16B	0.1285	0.3779	0.0269	0.088*
H16C	0.1575	0.3686	0.1076	0.088*
C17	0.1402 (2)	0.7456 (6)	0.1719 (3)	0.0437 (11)
C18	0.2141 (3)	0.9103 (8)	0.2484 (4)	0.0720 (14)
H18A	0.2214	1.0256	0.2574	0.108*
H18B	0.2409	0.8602	0.2438	0.108*
H18C	0.2141	0.8600	0.2860	0.108*
C19	0.0734 (3)	0.3785 (6)	0.3658 (4)	0.0590 (16)
H19A	0.0695	0.3336	0.4013	0.089*
H19B	0.1057	0.3382	0.3717	0.089*
H19C	0.0436	0.3459	0.3212	0.089*
C20	0.0691 (3)	1.1479 (9)	0.2166 (4)	0.0720 (14)
H20A	0.0732	1.2634	0.2267	0.108*
H20B	0.0364	1.1289	0.1729	0.108*
H20C	0.0985	1.1093	0.2145	0.108*

	U11	U22	U33	U12	U13	U23
Br1	0.0381 (3)	0.0527 (3)	0.0907 (5)	0.0122 (2)	0.0374 (3)	0.0068 (3)
Br2	0.0570 (3)	0.0430 (3)	0.0376 (3)	−0.0108 (2)	0.0324 (2)	−0.0123 (2)
O1	0.0330 (14)	0.0321 (15)	0.0452 (19)	0.0082 (11)	0.0272 (14)	0.0116 (13)
O2	0.058 (2)	0.0298 (15)	0.0372 (18)	−0.0026 (13)	0.0347 (17)	−0.0028 (13)
O3	0.0390 (18)	0.0438 (19)	0.096 (3)	−0.0040 (14)	0.043 (2)	−0.0001 (19)
O4	0.0391 (17)	0.0321 (16)	0.068 (3)	0.0026 (12)	0.0305 (18)	−0.0035 (16)
O5	0.048 (2)	0.067 (2)	0.040 (2)	−0.0182 (17)	0.0144 (18)	0.0008 (19)
O6	0.057 (2)	0.075 (3)	0.057 (3)	0.013 (2)	0.012 (2)	0.024 (2)
O7	0.062 (2)	0.0343 (17)	0.040 (2)	−0.0001 (14)	0.0346 (18)	0.0038 (14)
O8	0.056 (2)	0.0282 (15)	0.038 (2)	0.0019 (13)	0.0257 (17)	−0.0022 (14)
N1	0.0375 (19)	0.0338 (19)	0.048 (2)	0.0027 (14)	0.0270 (19)	0.0063 (17)
N2	0.0304 (16)	0.0305 (17)	0.036 (2)	0.0020 (13)	0.0180 (15)	−0.0021 (15)
N3	0.0444 (19)	0.0308 (18)	0.035 (2)	−0.0017 (14)	0.0279 (18)	−0.0015 (15)
N4	0.0391 (18)	0.0312 (17)	0.0285 (19)	0.0000 (14)	0.0202 (16)	0.0004 (15)
C1	0.035 (2)	0.038 (2)	0.042 (3)	0.0017 (17)	0.022 (2)	0.000 (2)
C2	0.035 (2)	0.037 (2)	0.046 (3)	0.0058 (17)	0.023 (2)	−0.001 (2)
C3	0.034 (2)	0.031 (2)	0.040 (3)	0.0046 (15)	0.0196 (19)	0.0021 (18)
C4	0.0302 (18)	0.037 (2)	0.028 (2)	0.0081 (15)	0.0168 (17)	0.0035 (18)
C5	0.0341 (19)	0.035 (2)	0.032 (2)	0.0063 (16)	0.0225 (18)	0.0031 (18)
C6	0.037 (2)	0.052 (3)	0.037 (3)	0.0065 (19)	0.022 (2)	0.011 (2)
C7	0.033 (2)	0.060 (3)	0.040 (3)	0.002 (2)	0.015 (2)	0.000 (2)
C8	0.038 (2)	0.049 (3)	0.038 (3)	−0.0044 (19)	0.022 (2)	−0.006 (2)
C9	0.044 (2)	0.031 (2)	0.036 (2)	0.0029 (16)	0.028 (2)	−0.0070 (18)
C10	0.038 (2)	0.031 (2)	0.029 (2)	0.0024 (16)	0.0204 (18)	−0.0012 (17)
C11	0.039 (2)	0.0274 (19)	0.033 (2)	−0.0021 (15)	0.0233 (19)	−0.0040 (17)
C12	0.0352 (19)	0.035 (2)	0.030 (2)	−0.0022 (16)	0.0214 (18)	0.0028 (18)
C13	0.0311 (18)	0.037 (2)	0.032 (2)	−0.0015 (15)	0.0199 (18)	−0.0054 (18)
C14	0.0306 (18)	0.0305 (19)	0.030 (2)	−0.0004 (14)	0.0169 (17)	−0.0062 (17)
C15	0.065 (4)	0.039 (3)	0.109 (6)	−0.011 (2)	0.055 (4)	−0.006 (3)
C16	0.045 (3)	0.037 (3)	0.093 (5)	−0.001 (2)	0.037 (3)	−0.002 (3)
C17	0.042 (2)	0.055 (3)	0.033 (3)	0.000 (2)	0.020 (2)	−0.004 (2)
C18	0.073 (3)	0.073 (3)	0.053 (3)	−0.018 (2)	0.023 (2)	0.003 (2)
C19	0.104 (5)	0.032 (2)	0.054 (4)	0.000 (3)	0.052 (4)	0.006 (2)
C20	0.073 (3)	0.073 (3)	0.053 (3)	−0.018 (2)	0.023 (2)	0.003 (2)

Br1—C2	1.872 (4)	C5—C6	1.386 (7)
Br2—C13	1.887 (4)	C5—C10	1.401 (6)
O1—C4	1.368 (5)	C6—C7	1.363 (7)
O1—C5	1.388 (5)	C6—H6A	0.9300
O2—C11	1.342 (5)	C7—C8	1.373 (8)
O2—C9	1.412 (6)	C7—H7A	0.9300
O3—C1	1.324 (6)	C8—C9	1.384 (7)
O3—C15	1.443 (6)	C8—H8A	0.9300
O4—C3	1.337 (5)	C9—C10	1.374 (6)
O4—C16	1.411 (6)	C10—C17	1.496 (7)
O5—C17	1.297 (6)	C12—C13	1.376 (6)
O5—C18	1.433 (8)	C13—C14	1.356 (6)
O6—C17	1.213 (7)	C15—H15A	0.9600
O7—C12	1.336 (5)	C15—H15B	0.9600
O7—C19	1.464 (6)	C15—H15C	0.9600
O8—C14	1.341 (5)	C16—H16A	0.9600
O8—C20	1.442 (8)	C16—H16B	0.9600
N1—C1	1.327 (6)	C16—H16C	0.9600
N1—C4	1.335 (6)	C18—H18A	0.9600
N2—C4	1.312 (6)	C18—H18B	0.9600
N2—C3	1.328 (5)	C18—H18C	0.9600
N3—C11	1.308 (6)	C19—H19A	0.9600
N3—C12	1.339 (6)	C19—H19B	0.9600
N4—C11	1.323 (5)	C19—H19C	0.9600
N4—C14	1.334 (6)	C20—H20A	0.9600
C1—C2	1.383 (6)	C20—H20B	0.9600
C2—C3	1.380 (6)	C20—H20C	0.9600
C4—O1—C5	117.6 (3)	N4—C11—O2	118.2 (4)
C11—O2—C9	118.4 (3)	O7—C12—N3	119.6 (4)
C1—O3—C15	118.4 (4)	O7—C12—C13	118.1 (4)
C3—O4—C16	117.6 (4)	N3—C12—C13	122.3 (4)
C17—O5—C18	119.2 (5)	C14—C13—C12	117.1 (4)
C12—O7—C19	118.0 (4)	C14—C13—Br2	122.1 (3)
C14—O8—C20	118.4 (5)	C12—C13—Br2	120.8 (4)
C1—N1—C4	113.8 (4)	N4—C14—O8	118.8 (4)
C4—N2—C3	114.4 (4)	N4—C14—C13	122.2 (4)
C11—N3—C12	114.7 (4)	O8—C14—C13	119.0 (4)
C11—N4—C14	115.3 (4)	O3—C15—H15A	109.5
O3—C1—N1	119.6 (4)	O3—C15—H15B	109.5
O3—C1—C2	117.7 (4)	H15A—C15—H15B	109.5
N1—C1—C2	122.4 (4)	O3—C15—H15C	109.5
C3—C2—C1	116.9 (4)	H15A—C15—H15C	109.5
C3—C2—Br1	121.9 (3)	H15B—C15—H15C	109.5
C1—C2—Br1	121.1 (3)	O4—C16—H16A	109.5
N2—C3—O4	118.6 (4)	O4—C16—H16B	109.5
N2—C3—C2	122.4 (4)	H16A—C16—H16B	109.5
O4—C3—C2	119.0 (4)	O4—C16—H16C	109.5
N2—C4—N1	129.8 (4)	H16A—C16—H16C	109.5
N2—C4—O1	117.6 (4)	H16B—C16—H16C	109.5
N1—C4—O1	112.6 (4)	O6—C17—O5	123.8 (5)
C6—C5—O1	117.0 (4)	O6—C17—C10	124.0 (5)
C6—C5—C10	120.5 (4)	O5—C17—C10	112.2 (4)
O1—C5—C10	122.5 (4)	O5—C18—H18A	109.5
C7—C6—C5	120.6 (5)	O5—C18—H18B	109.5
C7—C6—H6A	119.7	H18A—C18—H18B	109.5
C5—C6—H6A	119.7	O5—C18—H18C	109.5
C6—C7—C8	120.0 (5)	H18A—C18—H18C	109.5
C6—C7—H7A	120.0	H18B—C18—H18C	109.5
C8—C7—H7A	120.0	O7—C19—H19A	109.5
C7—C8—C9	119.3 (4)	O7—C19—H19B	109.5
C7—C8—H8A	120.3	H19A—C19—H19B	109.5
C9—C8—H8A	120.3	O7—C19—H19C	109.5
C10—C9—C8	122.3 (4)	H19A—C19—H19C	109.5
C10—C9—O2	121.0 (4)	H19B—C19—H19C	109.5
C8—C9—O2	116.7 (4)	O8—C20—H20A	109.5
C9—C10—C5	117.2 (4)	O8—C20—H20B	109.5
C9—C10—C17	121.5 (4)	H20A—C20—H20B	109.5
C5—C10—C17	121.2 (4)	O8—C20—H20C	109.5
N3—C11—N4	128.3 (4)	H20A—C20—H20C	109.5
N3—C11—O2	113.5 (3)	H20B—C20—H20C	109.5
C15—O3—C1—N1	−4.0 (8)	C8—C9—C10—C17	−179.4 (4)
C15—O3—C1—C2	−177.8 (6)	O2—C9—C10—C17	−1.0 (6)
C4—N1—C1—O3	−179.2 (5)	C6—C5—C10—C9	3.4 (6)
C4—N1—C1—C2	−5.6 (7)	O1—C5—C10—C9	179.2 (4)
O3—C1—C2—C3	178.6 (5)	C6—C5—C10—C17	−179.9 (4)
N1—C1—C2—C3	4.9 (8)	O1—C5—C10—C17	−4.1 (6)
O3—C1—C2—Br1	−5.6 (7)	C12—N3—C11—N4	1.2 (7)
N1—C1—C2—Br1	−179.2 (4)	C12—N3—C11—O2	−179.2 (4)
C4—N2—C3—O4	177.9 (5)	C14—N4—C11—N3	−2.2 (7)
C4—N2—C3—C2	−1.0 (7)	C14—N4—C11—O2	178.3 (4)
C16—O4—C3—N2	−2.1 (7)	C9—O2—C11—N3	178.6 (4)
C16—O4—C3—C2	176.8 (5)	C9—O2—C11—N4	−1.8 (6)
C1—C2—C3—N2	−1.4 (8)	C19—O7—C12—N3	−0.9 (7)
Br1—C2—C3—N2	−177.1 (4)	C19—O7—C12—C13	−180.0 (5)
C1—C2—C3—O4	179.8 (5)	C11—N3—C12—O7	−179.3 (4)
Br1—C2—C3—O4	4.0 (7)	C11—N3—C12—C13	−0.3 (6)
C3—N2—C4—N1	0.0 (7)	O7—C12—C13—C14	179.5 (4)
C3—N2—C4—O1	179.8 (4)	N3—C12—C13—C14	0.4 (6)
C1—N1—C4—N2	3.2 (8)	O7—C12—C13—Br2	1.1 (5)
C1—N1—C4—O1	−176.5 (4)	N3—C12—C13—Br2	−178.0 (3)
C5—O1—C4—N2	12.3 (6)	C11—N4—C14—O8	−179.9 (4)
C5—O1—C4—N1	−167.9 (4)	C11—N4—C14—C13	2.2 (6)
C4—O1—C5—C6	−121.7 (5)	C20—O8—C14—N4	−6.1 (6)
C4—O1—C5—C10	62.4 (5)	C20—O8—C14—C13	171.9 (5)
O1—C5—C6—C7	−177.4 (4)	C12—C13—C14—N4	−1.4 (6)
C10—C5—C6—C7	−1.4 (7)	Br2—C13—C14—N4	177.0 (3)
C5—C6—C7—C8	−1.4 (8)	C12—C13—C14—O8	−179.4 (4)
C6—C7—C8—C9	2.1 (8)	Br2—C13—C14—O8	−1.0 (5)
C7—C8—C9—C10	0.1 (7)	C18—O5—C17—O6	−2.0 (9)
C7—C8—C9—O2	−178.4 (4)	C18—O5—C17—C10	176.5 (5)
C11—O2—C9—C10	72.1 (5)	C9—C10—C17—O6	39.9 (7)
C11—O2—C9—C8	−109.4 (5)	C5—C10—C17—O6	−136.6 (6)
C8—C9—C10—C5	−2.8 (6)	C9—C10—C17—O5	−138.5 (5)
O2—C9—C10—C5	175.7 (4)	C5—C10—C17—O5	44.9 (6)