Methyl 3,5-bis-[(3-chloro-pyrazin-2-yl)-oxy]benzoate.

In the title compound, C16H10Cl2N4O4, the pyrazine rings make dihedral angles of 67.82 (9) and 75.91 (9)° with the benzene ring, while the dihedral angle between the pyrazine rings is 44.69 (10)°. The meth-oxy-carbonyl group makes a dihedral angle of 16.82 (8)° with the benzene ring to which it is attached. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules, forming chains running along the ab plane.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ▶); Dubinina et al. (2006 ▶); Ellsworth et al. (2007 ▶); Mukaiyama et al. (2007 ▶). For a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C16H10Cl2N4O4

M = 393.18

Triclinic,

a = 8.5437 (15) Å

b = 9.2984 (18) Å

c = 11.545 (2) Å

α = 88.592 (10)°

β = 74.974 (9)°

γ = 73.231 (9)°

V = 846.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.886, T max = 0.922

12425 measured reflections

3453 independent reflections

3076 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.124

S = 1.04

3453 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010465/pv2625sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010465/pv2625Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010465/pv2625Isup3.cml

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

C16H10Cl2N4O4	Z = 2
Mr = 393.18	F(000) = 400
Triclinic, P1	Dx = 1.542 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5437 (15) Å	Cell parameters from 3453 reflections
b = 9.2984 (18) Å	θ = 1.8–26.6°
c = 11.545 (2) Å	µ = 0.41 mm−1
α = 88.592 (10)°	T = 293 K
β = 74.974 (9)°	Block, colourless
γ = 73.231 (9)°	0.30 × 0.25 × 0.20 mm
V = 846.9 (3) Å3

Bruker SMART APEXII area-detector diffractometer	3453 independent reflections
Radiation source: fine-focus sealed tube	3076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 26.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.886, Tmax = 0.922	k = −11→11
12425 measured reflections	l = −14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.3652P] where P = (Fo2 + 2Fc2)/3
3453 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.46 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
C1	1.2164 (2)	−0.13661 (19)	0.56898 (15)	0.0357 (4)
C2	1.3326 (2)	−0.2435 (2)	0.48010 (16)	0.0392 (4)
C3	1.2200 (3)	−0.4217 (2)	0.5674 (2)	0.0512 (5)
H3	1.2182	−0.5212	0.5714	0.061*
C4	1.1050 (3)	−0.3171 (2)	0.65286 (19)	0.0486 (4)
H4	1.0265	−0.3476	0.7125	0.058*
C5	1.1396 (2)	0.10665 (18)	0.66279 (15)	0.0364 (4)
C6	1.1808 (2)	0.07829 (19)	0.77108 (16)	0.0377 (4)
H6	1.2538	−0.0136	0.7823	0.045*
C7	1.1100 (2)	0.19087 (19)	0.86279 (16)	0.0376 (4)
C8	0.9977 (2)	0.32842 (19)	0.84678 (16)	0.0394 (4)
H8	0.9532	0.4046	0.9073	0.047*
C9	0.9551 (2)	0.34790 (19)	0.73925 (17)	0.0376 (4)
C10	1.0255 (2)	0.23987 (19)	0.64574 (16)	0.0383 (4)
H10	0.9970	0.2562	0.5731	0.046*
C11	0.6780 (2)	0.5146 (2)	0.76707 (15)	0.0376 (4)
C12	0.5715 (2)	0.6516 (2)	0.74204 (17)	0.0443 (4)
C13	0.3460 (3)	0.5899 (3)	0.8520 (2)	0.0683 (7)
H13	0.2294	0.6121	0.8838	0.082*
C14	0.4482 (3)	0.4569 (3)	0.8760 (2)	0.0594 (6)
H14	0.3993	0.3908	0.9235	0.071*
C15	1.1546 (2)	0.1705 (2)	0.98024 (17)	0.0458 (4)
C16	1.2714 (4)	−0.0079 (3)	1.1083 (2)	0.0749 (8)
H16A	1.3582	0.0366	1.1128	0.112*
H16B	1.3125	−0.1150	1.1123	0.112*
H16C	1.1733	0.0318	1.1742	0.112*
N1	1.3349 (2)	−0.38465 (18)	0.47831 (15)	0.0479 (4)
N2	1.10203 (19)	−0.17218 (18)	0.65331 (14)	0.0427 (3)
N3	0.4081 (2)	0.6891 (2)	0.78443 (18)	0.0618 (5)
N4	0.6181 (2)	0.41812 (19)	0.83301 (15)	0.0462 (4)
O1	1.22265 (18)	0.00741 (14)	0.56204 (11)	0.0460 (3)
O2	0.84699 (15)	0.48570 (14)	0.71782 (13)	0.0445 (3)
O3	1.1276 (3)	0.27208 (19)	1.05207 (15)	0.0702 (5)
O4	1.2263 (2)	0.02685 (17)	0.99597 (13)	0.0623 (4)
Cl1	1.47807 (7)	−0.18931 (7)	0.36871 (5)	0.06146 (19)
Cl2	0.65455 (7)	0.77453 (6)	0.65015 (6)	0.06183 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0370 (8)	0.0322 (8)	0.0376 (8)	−0.0068 (6)	−0.0133 (7)	0.0005 (7)
C2	0.0381 (8)	0.0391 (9)	0.0390 (9)	−0.0076 (7)	−0.0117 (7)	−0.0023 (7)
C3	0.0665 (13)	0.0348 (10)	0.0563 (12)	−0.0176 (9)	−0.0197 (10)	0.0023 (8)
C4	0.0532 (11)	0.0477 (11)	0.0505 (11)	−0.0232 (9)	−0.0137 (9)	0.0039 (9)
C5	0.0381 (8)	0.0292 (8)	0.0387 (9)	−0.0092 (6)	−0.0052 (7)	−0.0010 (7)
C6	0.0351 (8)	0.0289 (8)	0.0434 (9)	−0.0028 (6)	−0.0078 (7)	0.0018 (7)
C7	0.0357 (8)	0.0336 (8)	0.0402 (9)	−0.0070 (7)	−0.0082 (7)	0.0030 (7)
C8	0.0371 (8)	0.0315 (8)	0.0433 (9)	−0.0049 (7)	−0.0050 (7)	−0.0018 (7)
C9	0.0310 (8)	0.0283 (8)	0.0498 (10)	−0.0052 (6)	−0.0087 (7)	0.0068 (7)
C10	0.0391 (9)	0.0361 (9)	0.0410 (9)	−0.0112 (7)	−0.0128 (7)	0.0059 (7)
C11	0.0367 (8)	0.0358 (9)	0.0377 (9)	−0.0049 (7)	−0.0113 (7)	−0.0021 (7)
C12	0.0453 (10)	0.0402 (10)	0.0426 (9)	−0.0009 (8)	−0.0161 (8)	0.0015 (8)
C13	0.0368 (10)	0.0936 (19)	0.0598 (13)	−0.0022 (11)	−0.0063 (9)	0.0058 (13)
C14	0.0465 (11)	0.0787 (16)	0.0515 (12)	−0.0204 (11)	−0.0089 (9)	0.0103 (11)
C15	0.0447 (10)	0.0449 (10)	0.0424 (10)	−0.0061 (8)	−0.0100 (8)	0.0018 (8)
C16	0.0865 (18)	0.0765 (17)	0.0503 (13)	0.0020 (14)	−0.0283 (12)	0.0137 (12)
N1	0.0530 (9)	0.0366 (8)	0.0518 (9)	−0.0062 (7)	−0.0168 (7)	−0.0036 (7)
N2	0.0406 (8)	0.0419 (8)	0.0449 (8)	−0.0126 (6)	−0.0093 (6)	−0.0002 (6)
N3	0.0438 (9)	0.0655 (12)	0.0591 (11)	0.0096 (8)	−0.0132 (8)	0.0027 (9)
N4	0.0418 (8)	0.0467 (9)	0.0483 (9)	−0.0107 (7)	−0.0114 (7)	0.0056 (7)
O1	0.0592 (8)	0.0332 (6)	0.0397 (7)	−0.0130 (6)	−0.0035 (6)	−0.0006 (5)
O2	0.0352 (6)	0.0316 (6)	0.0607 (8)	−0.0030 (5)	−0.0107 (6)	0.0111 (6)
O3	0.1037 (14)	0.0530 (9)	0.0501 (9)	−0.0085 (9)	−0.0293 (9)	−0.0063 (7)
O4	0.0801 (11)	0.0483 (8)	0.0498 (8)	0.0040 (7)	−0.0279 (8)	0.0045 (7)
Cl1	0.0616 (3)	0.0610 (3)	0.0520 (3)	−0.0218 (3)	0.0069 (2)	−0.0066 (2)
Cl2	0.0665 (3)	0.0411 (3)	0.0743 (4)	−0.0066 (2)	−0.0239 (3)	0.0175 (2)

C1—N2	1.300 (2)	C9—C10	1.380 (3)
C1—O1	1.355 (2)	C9—O2	1.4057 (19)
C1—C2	1.407 (2)	C10—H10	0.9300
C2—N1	1.308 (2)	C11—N4	1.294 (2)
C2—Cl1	1.7185 (19)	C11—O2	1.356 (2)
C3—N1	1.340 (3)	C11—C12	1.409 (2)
C3—C4	1.370 (3)	C12—N3	1.297 (3)
C3—H3	0.9300	C12—Cl2	1.718 (2)
C4—N2	1.340 (3)	C13—N3	1.332 (3)
C4—H4	0.9300	C13—C14	1.362 (4)
C5—C6	1.384 (2)	C13—H13	0.9300
C5—C10	1.383 (2)	C14—N4	1.348 (3)
C5—O1	1.398 (2)	C14—H14	0.9300
C6—C7	1.393 (2)	C15—O3	1.203 (3)
C6—H6	0.9300	C15—O4	1.329 (2)
C7—C8	1.401 (2)	C16—O4	1.450 (3)
C7—C15	1.495 (3)	C16—H16A	0.9600
C8—C9	1.375 (3)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
N2—C1—O1	120.32 (16)	C5—C10—H10	120.8
N2—C1—C2	121.66 (16)	N4—C11—O2	120.75 (16)
O1—C1—C2	117.98 (15)	N4—C11—C12	121.81 (17)
N1—C2—C1	122.44 (17)	O2—C11—C12	117.44 (16)
N1—C2—Cl1	117.86 (14)	N3—C12—C11	122.06 (19)
C1—C2—Cl1	119.69 (14)	N3—C12—Cl2	117.28 (15)
N1—C3—C4	121.89 (18)	C11—C12—Cl2	120.64 (15)
N1—C3—H3	119.1	N3—C13—C14	121.9 (2)
C4—C3—H3	119.1	N3—C13—H13	119.0
N2—C4—C3	122.12 (18)	C14—C13—H13	119.0
N2—C4—H4	118.9	N4—C14—C13	122.0 (2)
C3—C4—H4	118.9	N4—C14—H14	119.0
C6—C5—C10	121.86 (16)	C13—C14—H14	119.0
C6—C5—O1	121.32 (15)	O3—C15—O4	124.21 (19)
C10—C5—O1	116.59 (15)	O3—C15—C7	123.90 (18)
C5—C6—C7	118.28 (15)	O4—C15—C7	111.88 (17)
C5—C6—H6	120.9	O4—C16—H16A	109.5
C7—C6—H6	120.9	O4—C16—H16B	109.5
C6—C7—C8	120.99 (16)	H16A—C16—H16B	109.5
C6—C7—C15	121.16 (15)	O4—C16—H16C	109.5
C8—C7—C15	117.83 (16)	H16A—C16—H16C	109.5
C9—C8—C7	118.26 (16)	H16B—C16—H16C	109.5
C9—C8—H8	120.9	C2—N1—C3	115.66 (17)
C7—C8—H8	120.9	C1—N2—C4	116.18 (17)
C8—C9—C10	122.16 (15)	C12—N3—C13	116.28 (19)
C8—C9—O2	120.22 (16)	C11—N4—C14	115.96 (18)
C10—C9—O2	117.42 (16)	C1—O1—C5	118.77 (13)
C9—C10—C5	118.35 (16)	C11—O2—C9	118.32 (13)
C9—C10—H10	120.8	C15—O4—C16	117.08 (18)
N2—C1—C2—N1	−1.4 (3)	C6—C7—C15—O4	−17.0 (3)
O1—C1—C2—N1	−179.07 (16)	C8—C7—C15—O4	164.56 (17)
N2—C1—C2—Cl1	178.52 (14)	C1—C2—N1—C3	−0.5 (3)
O1—C1—C2—Cl1	0.9 (2)	Cl1—C2—N1—C3	179.52 (14)
N1—C3—C4—N2	−0.9 (3)	C4—C3—N1—C2	1.6 (3)
C10—C5—C6—C7	−2.9 (3)	O1—C1—N2—C4	179.72 (16)
O1—C5—C6—C7	171.39 (15)	C2—C1—N2—C4	2.1 (3)
C5—C6—C7—C8	1.1 (3)	C3—C4—N2—C1	−1.0 (3)
C5—C6—C7—C15	−177.37 (16)	C11—C12—N3—C13	−0.8 (3)
C6—C7—C8—C9	1.9 (3)	Cl2—C12—N3—C13	177.75 (19)
C15—C7—C8—C9	−179.61 (16)	C14—C13—N3—C12	0.4 (4)
C7—C8—C9—C10	−3.3 (3)	O2—C11—N4—C14	−179.00 (18)
C7—C8—C9—O2	−178.05 (15)	C12—C11—N4—C14	0.0 (3)
C8—C9—C10—C5	1.5 (3)	C13—C14—N4—C11	−0.4 (3)
O2—C9—C10—C5	176.47 (15)	N2—C1—O1—C5	17.9 (2)
C6—C5—C10—C9	1.6 (3)	C2—C1—O1—C5	−164.46 (15)
O1—C5—C10—C9	−172.90 (15)	C6—C5—O1—C1	59.1 (2)
N4—C11—C12—N3	0.6 (3)	C10—C5—O1—C1	−126.30 (17)
O2—C11—C12—N3	179.63 (18)	N4—C11—O2—C9	0.6 (3)
N4—C11—C12—Cl2	−177.87 (15)	C12—C11—O2—C9	−178.44 (16)
O2—C11—C12—Cl2	1.2 (2)	C8—C9—O2—C11	−78.8 (2)
N3—C13—C14—N4	0.2 (4)	C10—C9—O2—C11	106.15 (18)
C6—C7—C15—O3	163.5 (2)	O3—C15—O4—C16	1.1 (3)
C8—C7—C15—O3	−15.0 (3)	C7—C15—O4—C16	−178.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.93	2.47	3.192 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.93	2.47	3.192 (3)	135

Symmetry code: (i) .