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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Jun 13;68(Pt 7):o2062. doi: 10.1107/S1600536812025767

2,4-Dibromo-1,3-dimeth­oxy-5-methyl­benzene

Sunayna Pawar a, Mahidansha Shaikh a, Neil Koorbanally a,*, Bernard Omondi a, Deresh Ramjugernath b
PMCID: PMC3393326  PMID: 22807883

Abstract

The title compound, C9H10Br2O2, crystallizes with two mol­ecules in the asymmetric unit. The two mol­ecules are essentially planar with slight differences in the (Br)C—C—O—C(H3) torsion angles [−176.7 (2) and −172.8 (2)° in one mol­ecule and 174.8 (2) and 179.9 (2)° in the other]. The crystal structure consists of sheets of mol­ecules linked through Br⋯Br [3.3547 (4), 3.3703 (4) and 3.5379 (4) Å] inter­actions, which are in turn connected through π–π inter­actions 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 ▶).graphic file with name e-68-o2062-scheme1.jpg

Experimental  

Crystal data  

  • C9H10Br2O2

  • M r = 309.99

  • Monoclinic, Inline graphic

  • 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 ▶).

Supplementary Material

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

e-68-o2062-sup1.cif (27.6KB, cif)

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

e-68-o2062-Isup2.hkl (238.9KB, hkl)

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

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

Acknowledgments

SP thanks the College of Agriculture, Engineering and Science of the University of KwaZulu-Natal for a doctoral bursary.

supplementary crystallographic information

Comment

The title compound (I), is an important precursor in the synthesis of 2,4-dihydroxy-1,3-dimethoxy-5-methylbenzene, a key intermediate in the synthesis of Drimiopsin A (Koorbanally et al., 2004).

The two molecules are essentialy planar with a mean plane deviation of -0.010 (1)°, -0.018 (1)°, 0.031 (1)° and 0.003 (1)° for Br1 to Br4 respectively. All bond distances and angles are within normal ranges (Allen et al., 1987) (Fig 1).

In the crystal, molecules are connected through three diferent Br···Br (Br1···Br1 = 3.3547 (4), Br2···Br2 = 3.3703 (4) and Br3···Br4 = 3.5379 (4) Å, Symmetry codes: 1 - x, -y, 2 - z; 1 - x, 1 - y, 2 - z; -1 + x, y, z) intermolecular interactions and a Br···O interaction (3.2657 (18) Å Symmetry code: -1 + x, y, z) resulting in sheets along the ab face. These sheets are in turn connected through π···π interactions with distances between 3.5902 (14) and 3.5956 (15) Å (Symmetry code: x, y, 1 - z).

Experimental

To a solution of 1,3-dimethyl-5-methylbenzene (1.0 g, 6.578 mmol,1 eq.) in water (40 ml), bromine (3.1 ml, 39.473 mmol, 6.0 eq.) was added at 0 oC and the resultant solution refluxed at 110 oC for 12 h. The reaction was monitored by TLC using EtOAc/ Hexane (5/95, Rf = 0.6). After completion of the reaction, the reaction mixture was diluted with ethyl acetate (30 ml) and washed with 20 ml of water. The organic layer was separated and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure to afford a crude mixture of dibromo and tribromo-compound. This was purified by column chromatography using 100% hexane. Colourless crystals were obtained by slow evaporation of the solvents from solutions of the title compound in a mixture of ethyl acetate and hexane to yield the title compound with a m.p. of 165–167 °C.

1H NMR (400 MHz, CDCl3): δ (p.p.m.): 6.42 (1H, s), 3.90 (6H, s), 2.61 (3H, s). 13C NMR (100 MHz, CDCl3): δ (p.p.m.): 155.9, 139.4, 105.9, 95.0, 56.7, 24.3

Refinement

All H atoms were positioned geometrically and allowed to ride on their respective parent atoms. The carboxyl H atoms were located from the difference map and allowed to ride on their parent atoms. All H atoms were refined isotropically.

Figures

Fig. 1.

Fig. 1.

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The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.

Crystal data

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
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Data collection

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
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Refinement

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
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Special details

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:
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2564).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-68-o2062-sup1.cif (27.6KB, cif)

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

e-68-o2062-Isup2.hkl (238.9KB, hkl)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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