2,4-Dibromo-1,3-dimeth-oxy-5-methyl-benzene.

The title compound, C(9)H(10)Br(2)O(2), crystallizes with two mol-ecules in the asymmetric unit. The two mol-ecules are essentially planar with slight differences in the (Br)C-C-O-C(H(3)) torsion angles [-176.7 (2) and -172.8 (2)° in one mol-ecule and 174.8 (2) and 179.9 (2)° in the other]. The crystal structure consists of sheets of mol-ecules linked through Br⋯Br [3.3547 (4), 3.3703 (4) and 3.5379 (4) Å] inter-actions, which are in turn connected through π-π inter-actions with centroid-centroid distances of 3.5902 (14) and 3.5956 (14) Å.

Related literature

For related structures, see: Hernandez et al. (2003 ▶); Cukiernik et al. (2008 ▶); Saeed et al. (2010 ▶); Koorbanally et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H10Br2O2

M = 309.99

Monoclinic,

a = 8.7653 (2) Å

b = 16.4434 (3) Å

c = 13.8895 (3) Å

β = 91.715 (1)°

V = 2001.02 (7) Å3

Z = 8

Mo Kα radiation

μ = 8.07 mm−1

T = 446 K

0.55 × 0.25 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.095, T max = 0.499

36582 measured reflections

4979 independent reflections

4447 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.076

S = 1.04

4979 reflections

241 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.69 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812025767/fj2564sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025767/fj2564Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025767/fj2564Isup3.cml

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

C9H10Br2O2	F(000) = 1200
Mr = 309.99	Dx = 2.058 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 37343 reflections
a = 8.7653 (2) Å	θ = 1.9–28.3°
b = 16.4434 (3) Å	µ = 8.07 mm−1
c = 13.8895 (3) Å	T = 446 K
β = 91.715 (1)°	Block, colourless
V = 2001.02 (7) Å3	0.55 × 0.25 × 0.10 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	4979 independent reflections
Radiation source: fine-focus sealed tube	4447 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.095, Tmax = 0.499	k = −21→20
36582 measured reflections	l = −18→18

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0416P)2 + 3.5276P] where P = (Fo2 + 2Fc2)/3
4979 reflections	(Δ/σ)max = 0.029
241 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

Experimental. Carbon-bound H-atoms were placed in calculated positions [C—H = 0.96 Å for Me H atoms and 0.93 Å for aromatic H atoms; Uiso(H) = 1.2Ueq(C) (1.5 for Me groups)] and were included in the refinement in the riding model approximation.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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.>>> The Following Model ALERTS were generated - (Acta-Mode) <<< Format: alert-number_ALERT_alert-type_alert-level text112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem··· ZAuthor response: No additional symmetry.912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 14 431_ALERT_2_G Short Inter HL..A Contact Br1.. Br1.. 3.35 A ng. 431_ALERT_2_G Short Inter HL..A Contact Br2.. Br2.. 3.37 A ng. 431_ALERT_2_G Short Inter HL..A Contact Br3.. Br4.. 3.54 A ng.Noted:

	x	y	z	Uiso*/Ueq
C1	0.7073 (3)	0.18056 (17)	0.96286 (18)	0.0134 (5)
C2	0.6244 (3)	0.25269 (17)	0.95874 (18)	0.0139 (5)
C3	0.7078 (3)	0.32456 (16)	0.95817 (18)	0.0125 (5)
C4	0.8676 (3)	0.32527 (16)	0.96239 (18)	0.0128 (5)
C5	0.9465 (3)	0.25226 (15)	0.96624 (18)	0.0126 (5)
H5	1.0526	0.2522	0.9683	0.015*
C6	0.8670 (3)	0.17921 (17)	0.96708 (18)	0.0137 (5)
C7	0.4523 (3)	0.25224 (18)	0.9553 (2)	0.0194 (6)
H7A	0.4161	0.2323	0.8938	0.029*
H7B	0.4153	0.3065	0.9647	0.029*
H7C	0.4160	0.2176	1.0053	0.029*
C8	1.1004 (3)	0.4005 (2)	0.9614 (2)	0.0225 (6)
H8A	1.1412	0.3740	1.0181	0.034*
H8B	1.1352	0.4558	0.9602	0.034*
H8C	1.1342	0.3725	0.9052	0.034*
C9	1.0984 (3)	0.10374 (19)	0.9875 (2)	0.0219 (6)
H9A	1.1471	0.1228	0.9308	0.033*
H9B	1.1310	0.0491	1.0014	0.033*
H9C	1.1259	0.1384	1.0409	0.033*
C10	0.8338 (3)	0.23502 (18)	0.71339 (18)	0.0139 (5)
C11	0.7952 (3)	0.31760 (18)	0.71368 (18)	0.0138 (5)
C12	0.6418 (3)	0.33975 (17)	0.71153 (18)	0.0131 (5)
H12	0.6145	0.3944	0.7121	0.016*
C13	0.5294 (3)	0.28001 (17)	0.70859 (18)	0.0125 (5)
C14	0.5708 (3)	0.19796 (17)	0.70738 (18)	0.0129 (5)
C15	0.7239 (3)	0.17377 (17)	0.70967 (18)	0.0134 (5)
C16	0.7691 (3)	0.08609 (18)	0.7087 (2)	0.0186 (6)
H16A	0.8527	0.0788	0.6664	0.028*
H16B	0.6840	0.0538	0.6864	0.028*
H16C	0.7997	0.0694	0.7726	0.028*
C17	0.3326 (3)	0.38005 (18)	0.7161 (2)	0.0190 (6)
H17A	0.3769	0.4020	0.7746	0.028*
H17B	0.2234	0.3834	0.7180	0.028*
H17C	0.3676	0.4106	0.6622	0.028*
C18	0.8728 (4)	0.45640 (19)	0.7160 (2)	0.0241 (6)
H18A	0.8046	0.4679	0.6624	0.036*
H18B	0.9638	0.4885	0.7109	0.036*
H18C	0.8238	0.4695	0.7750	0.036*
O1	0.9371 (2)	0.39911 (12)	0.96234 (15)	0.0170 (4)
O2	0.9358 (2)	0.10511 (12)	0.97172 (15)	0.0180 (4)
O3	0.3772 (2)	0.29668 (12)	0.70659 (14)	0.0162 (4)
O4	0.9121 (2)	0.37173 (12)	0.71589 (15)	0.0189 (4)
Br1	0.60437 (3)	0.078949 (17)	0.96307 (2)	0.01967 (8)
Br2	0.60863 (3)	0.427111 (17)	0.95128 (2)	0.01804 (8)
Br3	1.04452 (3)	0.208463 (18)	0.718591 (18)	0.01701 (8)
Br4	0.41110 (3)	0.120197 (17)	0.70330 (2)	0.01769 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0170 (13)	0.0102 (12)	0.0129 (11)	−0.0039 (10)	0.0000 (9)	0.0017 (9)
C2	0.0138 (12)	0.0178 (14)	0.0103 (11)	−0.0007 (10)	0.0013 (9)	−0.0017 (10)
C3	0.0153 (12)	0.0088 (12)	0.0134 (11)	0.0039 (9)	0.0009 (9)	−0.0014 (9)
C4	0.0161 (12)	0.0104 (12)	0.0121 (11)	−0.0012 (10)	0.0013 (9)	−0.0015 (9)
C5	0.0123 (12)	0.0122 (13)	0.0134 (11)	0.0019 (9)	0.0007 (9)	0.0004 (9)
C6	0.0168 (12)	0.0121 (13)	0.0123 (11)	0.0020 (10)	0.0000 (9)	0.0005 (10)
C7	0.0144 (13)	0.0213 (16)	0.0224 (14)	0.0007 (11)	0.0020 (10)	−0.0010 (11)
C8	0.0170 (14)	0.0199 (15)	0.0308 (16)	−0.0039 (11)	0.0042 (12)	−0.0013 (12)
C9	0.0206 (14)	0.0145 (14)	0.0302 (15)	0.0060 (11)	−0.0040 (11)	−0.0006 (12)
C10	0.0070 (11)	0.0224 (14)	0.0122 (11)	0.0004 (10)	0.0005 (9)	−0.0001 (10)
C11	0.0098 (11)	0.0187 (14)	0.0129 (11)	−0.0046 (10)	0.0001 (9)	0.0003 (10)
C12	0.0126 (12)	0.0126 (13)	0.0141 (11)	0.0012 (10)	−0.0001 (9)	0.0014 (10)
C13	0.0099 (11)	0.0166 (13)	0.0111 (11)	0.0013 (10)	0.0010 (9)	−0.0016 (10)
C14	0.0097 (11)	0.0147 (13)	0.0141 (11)	−0.0028 (10)	0.0003 (9)	−0.0008 (10)
C15	0.0130 (12)	0.0158 (13)	0.0113 (11)	0.0014 (10)	0.0002 (9)	−0.0016 (10)
C16	0.0147 (13)	0.0153 (14)	0.0259 (14)	0.0041 (10)	0.0019 (10)	0.0023 (11)
C17	0.0132 (12)	0.0210 (15)	0.0226 (13)	0.0035 (11)	−0.0014 (10)	−0.0012 (11)
C18	0.0200 (14)	0.0161 (15)	0.0362 (17)	−0.0078 (12)	−0.0010 (12)	0.0002 (13)
O1	0.0148 (9)	0.0095 (9)	0.0269 (10)	−0.0020 (7)	0.0015 (8)	0.0001 (8)
O2	0.0180 (10)	0.0090 (9)	0.0268 (10)	0.0020 (8)	−0.0022 (8)	0.0012 (8)
O3	0.0084 (8)	0.0163 (10)	0.0239 (10)	0.0015 (7)	0.0012 (7)	−0.0024 (8)
O4	0.0127 (9)	0.0163 (11)	0.0277 (10)	−0.0044 (8)	0.0015 (8)	−0.0017 (8)
Br1	0.02245 (15)	0.01443 (15)	0.02218 (14)	−0.00754 (10)	0.00115 (11)	−0.00034 (10)
Br2	0.01823 (14)	0.01405 (14)	0.02181 (14)	0.00654 (10)	−0.00010 (10)	−0.00210 (10)
Br3	0.00848 (12)	0.02530 (16)	0.01724 (13)	0.00245 (10)	0.00042 (9)	−0.00052 (10)
Br4	0.01199 (13)	0.01491 (14)	0.02615 (15)	−0.00285 (10)	0.00015 (10)	−0.00184 (10)

C1—C2	1.391 (4)	C10—C15	1.394 (4)
C1—C6	1.400 (4)	C10—C11	1.399 (4)
C1—Br1	1.899 (3)	C10—Br3	1.897 (3)
C2—C3	1.390 (4)	C11—O4	1.357 (3)
C2—C7	1.508 (4)	C11—C12	1.392 (4)
C3—C4	1.400 (4)	C12—C13	1.391 (4)
C3—Br2	1.898 (3)	C12—H12	0.9300
C4—O1	1.359 (3)	C13—O3	1.361 (3)
C4—C5	1.386 (4)	C13—C14	1.397 (4)
C5—C6	1.389 (4)	C14—C15	1.400 (4)
C5—H5	0.9300	C14—Br4	1.895 (3)
C6—O2	1.360 (3)	C15—C16	1.495 (4)
C7—H7A	0.9600	C16—H16A	0.9600
C7—H7B	0.9600	C16—H16B	0.9600
C7—H7C	0.9600	C16—H16C	0.9600
C8—O1	1.431 (3)	C17—O3	1.433 (4)
C8—H8A	0.9600	C17—H17A	0.9600
C8—H8B	0.9600	C17—H17B	0.9600
C8—H8C	0.9600	C17—H17C	0.9600
C9—O2	1.436 (3)	C18—O4	1.434 (4)
C9—H9A	0.9600	C18—H18A	0.9600
C9—H9B	0.9600	C18—H18B	0.9600
C9—H9C	0.9600	C18—H18C	0.9600
C2—C1—C6	122.4 (2)	C11—C10—Br3	117.3 (2)
C2—C1—Br1	120.2 (2)	O4—C11—C12	123.8 (3)
C6—C1—Br1	117.4 (2)	O4—C11—C10	117.0 (2)
C3—C2—C1	116.8 (2)	C12—C11—C10	119.2 (2)
C3—C2—C7	122.0 (2)	C13—C12—C11	119.9 (3)
C1—C2—C7	121.2 (2)	C13—C12—H12	120.0
C2—C3—C4	122.2 (2)	C11—C12—H12	120.0
C2—C3—Br2	121.0 (2)	O3—C13—C12	123.4 (2)
C4—C3—Br2	116.8 (2)	O3—C13—C14	116.7 (2)
O1—C4—C5	123.4 (2)	C12—C13—C14	119.9 (2)
O1—C4—C3	117.1 (2)	C13—C14—C15	121.5 (2)
C5—C4—C3	119.5 (2)	C13—C14—Br4	117.40 (19)
C4—C5—C6	120.0 (3)	C15—C14—Br4	121.1 (2)
C4—C5—H5	120.0	C10—C15—C14	117.2 (3)
C6—C5—H5	120.0	C10—C15—C16	120.9 (2)
O2—C6—C5	123.6 (2)	C14—C15—C16	121.9 (2)
O2—C6—C1	117.2 (2)	C15—C16—H16A	109.5
C5—C6—C1	119.2 (2)	C15—C16—H16B	109.5
C2—C7—H7A	109.5	H16A—C16—H16B	109.5
C2—C7—H7B	109.5	C15—C16—H16C	109.5
H7A—C7—H7B	109.5	H16A—C16—H16C	109.5
C2—C7—H7C	109.5	H16B—C16—H16C	109.5
H7A—C7—H7C	109.5	O3—C17—H17A	109.5
H7B—C7—H7C	109.5	O3—C17—H17B	109.5
O1—C8—H8A	109.5	H17A—C17—H17B	109.5
O1—C8—H8B	109.5	O3—C17—H17C	109.5
H8A—C8—H8B	109.5	H17A—C17—H17C	109.5
O1—C8—H8C	109.5	H17B—C17—H17C	109.5
H8A—C8—H8C	109.5	O4—C18—H18A	109.5
H8B—C8—H8C	109.5	O4—C18—H18B	109.5
O2—C9—H9A	109.5	H18A—C18—H18B	109.5
O2—C9—H9B	109.5	O4—C18—H18C	109.5
H9A—C9—H9B	109.5	H18A—C18—H18C	109.5
O2—C9—H9C	109.5	H18B—C18—H18C	109.5
H9A—C9—H9C	109.5	C4—O1—C8	117.5 (2)
H9B—C9—H9C	109.5	C6—O2—C9	117.2 (2)
C15—C10—C11	122.3 (2)	C13—O3—C17	117.4 (2)
C15—C10—Br3	120.4 (2)	C11—O4—C18	117.1 (2)
C6—C1—C2—C3	0.5 (4)	O4—C11—C12—C13	179.5 (2)
Br1—C1—C2—C3	−179.56 (18)	C10—C11—C12—C13	−0.4 (4)
C6—C1—C2—C7	−179.3 (2)	C11—C12—C13—O3	179.8 (2)
Br1—C1—C2—C7	0.6 (3)	C11—C12—C13—C14	−0.3 (4)
C1—C2—C3—C4	−0.6 (4)	O3—C13—C14—C15	−179.7 (2)
C7—C2—C3—C4	179.3 (2)	C12—C13—C14—C15	0.4 (4)
C1—C2—C3—Br2	179.30 (18)	O3—C13—C14—Br4	−0.1 (3)
C7—C2—C3—Br2	−0.9 (3)	C12—C13—C14—Br4	−179.97 (19)
C2—C3—C4—O1	−179.4 (2)	C11—C10—C15—C14	−0.8 (4)
Br2—C3—C4—O1	0.8 (3)	Br3—C10—C15—C14	179.08 (18)
C2—C3—C4—C5	0.7 (4)	C11—C10—C15—C16	179.5 (2)
Br2—C3—C4—C5	−179.16 (19)	Br3—C10—C15—C16	−0.6 (3)
O1—C4—C5—C6	179.3 (2)	C13—C14—C15—C10	0.1 (4)
C3—C4—C5—C6	−0.8 (4)	Br4—C14—C15—C10	−179.50 (18)
C4—C5—C6—O2	−179.3 (2)	C13—C14—C15—C16	179.8 (2)
C4—C5—C6—C1	0.7 (4)	Br4—C14—C15—C16	0.2 (3)
C2—C1—C6—O2	179.4 (2)	C5—C4—O1—C8	3.2 (4)
Br1—C1—C6—O2	−0.5 (3)	C3—C4—O1—C8	−176.7 (2)
C2—C1—C6—C5	−0.6 (4)	C5—C6—O2—C9	7.2 (4)
Br1—C1—C6—C5	179.45 (19)	C1—C6—O2—C9	−172.8 (2)
C15—C10—C11—O4	−179.0 (2)	C12—C13—O3—C17	−5.3 (4)
Br3—C10—C11—O4	1.2 (3)	C14—C13—O3—C17	174.8 (2)
C15—C10—C11—C12	0.9 (4)	C12—C11—O4—C18	0.0 (4)
Br3—C10—C11—C12	−178.96 (19)	C10—C11—O4—C18	179.9 (2)