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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2062
https://doi.org/10.1107/S1600536812025767

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

Sunayna Pawar,a Mahidansha Shaikh,a Neil Koorbanally,a* Bernard Omondia and Deresh Ramjugernathb

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa, and bSchool of Engineering, University of KwaZulu-Natal, Howard College Campus, Private Bag X54001, Durban, 4000, South Africa
*Correspondence e-mail: Koorbanally@ukzn.ac.za

(Received 23 May 2012; accepted 6 June 2012; online 13 June 2012)

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[Hernandez, O., Cousson, A., Plazanet, M., Nierlich, M. & Meinnel, J. (2003). Acta Cryst. C59, o445-o450.]); Cukiernik et al. (2008[Cukiernik, F. D., Zelcer, A., Garland, M. T. & Baggio, R. (2008). Acta Cryst. C64, o604-o608.]); Saeed et al. (2010[Saeed, A., Rafique, H., Simpson, J. & Ashraf, Z. (2010). Acta Cryst. E66, o982-o983.]); Koorbanally et al. (2004[Koorbanally, C., Mulholland, D. A., Crouch, N. R. & Sandor, P. (2004). J. Nat. Prod. 67, 1726-1728.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.]).

[Scheme 1]

Experimental

Crystal data

  • C9H10Br2O2

  • Mr = 309.99

  • Monoclinic, P 21 /c

  • 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[Bruker (2008). APEX2, SAINT-Plus and SADABS. BrukerAXS Inc, Madison, Wisconsin, USA.]) Tmin = 0.095, Tmax = 0.499

  • 36582 measured reflections

  • 4979 independent reflections

  • 4447 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.027

  • wR(F2) = 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[Bruker (2008). APEX2, SAINT-Plus and SADABS. BrukerAXS Inc, Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. BrukerAXS Inc, Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. BrukerAXS Inc, Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536812025767/fj2564sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025767/fj2564Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025767/fj2564Isup3.cml

checkCIF report


Comment top

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).

Related literature top

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 top

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 top

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.

Structure description top

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).

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level.
2,4-Dibromo-1,3-dimethoxy-5-methylbenzene top
Crystal data top
C9H10Br2O2F(000) = 1200
Mr = 309.99Dx = 2.058 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 37343 reflections
a = 8.7653 (2) Åθ = 1.9–28.3°
b = 16.4434 (3) ŵ = 8.07 mm−1
c = 13.8895 (3) ÅT = 446 K
β = 91.715 (1)°Block, colourless
V = 2001.02 (7) Å30.55 × 0.25 × 0.10 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD
diffractometer		4979 independent reflections
Radiation source: fine-focus sealed tube4447 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		h = −11→11
Tmin = 0.095, Tmax = 0.499k = −21→20
36582 measured reflectionsl = −18→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-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 parametersΔρmax = 0.79 e Å−3
0 restraintsΔρmin = −0.69 e Å−3
Crystal data top
C9H10Br2O2V = 2001.02 (7) Å3
Mr = 309.99Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.7653 (2) ŵ = 8.07 mm−1
b = 16.4434 (3) ÅT = 446 K
c = 13.8895 (3) Å0.55 × 0.25 × 0.10 mm
β = 91.715 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		4979 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)		4447 reflections with I > 2σ(I)
Tmin = 0.095, Tmax = 0.499Rint = 0.037
36582 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0270 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.04Δρmax = 0.79 e Å−3
4979 reflectionsΔρmin = −0.69 e Å−3
241 parameters
Special details top

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 text

112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem··· Z

Author 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:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7073 (3)0.18056 (17)0.96286 (18)0.0134 (5)
C20.6244 (3)0.25269 (17)0.95874 (18)0.0139 (5)
C30.7078 (3)0.32456 (16)0.95817 (18)0.0125 (5)
C40.8676 (3)0.32527 (16)0.96239 (18)0.0128 (5)
C50.9465 (3)0.25226 (15)0.96624 (18)0.0126 (5)
H51.05260.25220.96830.015*
C60.8670 (3)0.17921 (17)0.96708 (18)0.0137 (5)
C70.4523 (3)0.25224 (18)0.9553 (2)0.0194 (6)
H7A0.41610.23230.89380.029*
H7B0.41530.30650.96470.029*
H7C0.41600.21761.00530.029*
C81.1004 (3)0.4005 (2)0.9614 (2)0.0225 (6)
H8A1.14120.37401.01810.034*
H8B1.13520.45580.96020.034*
H8C1.13420.37250.90520.034*
C91.0984 (3)0.10374 (19)0.9875 (2)0.0219 (6)
H9A1.14710.12280.93080.033*
H9B1.13100.04911.00140.033*
H9C1.12590.13841.04090.033*
C100.8338 (3)0.23502 (18)0.71339 (18)0.0139 (5)
C110.7952 (3)0.31760 (18)0.71368 (18)0.0138 (5)
C120.6418 (3)0.33975 (17)0.71153 (18)0.0131 (5)
H120.61450.39440.71210.016*
C130.5294 (3)0.28001 (17)0.70859 (18)0.0125 (5)
C140.5708 (3)0.19796 (17)0.70738 (18)0.0129 (5)
C150.7239 (3)0.17377 (17)0.70967 (18)0.0134 (5)
C160.7691 (3)0.08609 (18)0.7087 (2)0.0186 (6)
H16A0.85270.07880.66640.028*
H16B0.68400.05380.68640.028*
H16C0.79970.06940.77260.028*
C170.3326 (3)0.38005 (18)0.7161 (2)0.0190 (6)
H17A0.37690.40200.77460.028*
H17B0.22340.38340.71800.028*
H17C0.36760.41060.66220.028*
C180.8728 (4)0.45640 (19)0.7160 (2)0.0241 (6)
H18A0.80460.46790.66240.036*
H18B0.96380.48850.71090.036*
H18C0.82380.46950.77500.036*
O10.9371 (2)0.39911 (12)0.96234 (15)0.0170 (4)
O20.9358 (2)0.10511 (12)0.97172 (15)0.0180 (4)
O30.3772 (2)0.29668 (12)0.70659 (14)0.0162 (4)
O40.9121 (2)0.37173 (12)0.71589 (15)0.0189 (4)
Br10.60437 (3)0.078949 (17)0.96307 (2)0.01967 (8)
Br20.60863 (3)0.427111 (17)0.95128 (2)0.01804 (8)
Br31.04452 (3)0.208463 (18)0.718591 (18)0.01701 (8)
Br40.41110 (3)0.120197 (17)0.70330 (2)0.01769 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0170 (13)0.0102 (12)0.0129 (11)−0.0039 (10)0.0000 (9)0.0017 (9)
C20.0138 (12)0.0178 (14)0.0103 (11)−0.0007 (10)0.0013 (9)−0.0017 (10)
C30.0153 (12)0.0088 (12)0.0134 (11)0.0039 (9)0.0009 (9)−0.0014 (9)
C40.0161 (12)0.0104 (12)0.0121 (11)−0.0012 (10)0.0013 (9)−0.0015 (9)
C50.0123 (12)0.0122 (13)0.0134 (11)0.0019 (9)0.0007 (9)0.0004 (9)
C60.0168 (12)0.0121 (13)0.0123 (11)0.0020 (10)0.0000 (9)0.0005 (10)
C70.0144 (13)0.0213 (16)0.0224 (14)0.0007 (11)0.0020 (10)−0.0010 (11)
C80.0170 (14)0.0199 (15)0.0308 (16)−0.0039 (11)0.0042 (12)−0.0013 (12)
C90.0206 (14)0.0145 (14)0.0302 (15)0.0060 (11)−0.0040 (11)−0.0006 (12)
C100.0070 (11)0.0224 (14)0.0122 (11)0.0004 (10)0.0005 (9)−0.0001 (10)
C110.0098 (11)0.0187 (14)0.0129 (11)−0.0046 (10)0.0001 (9)0.0003 (10)
C120.0126 (12)0.0126 (13)0.0141 (11)0.0012 (10)−0.0001 (9)0.0014 (10)
C130.0099 (11)0.0166 (13)0.0111 (11)0.0013 (10)0.0010 (9)−0.0016 (10)
C140.0097 (11)0.0147 (13)0.0141 (11)−0.0028 (10)0.0003 (9)−0.0008 (10)
C150.0130 (12)0.0158 (13)0.0113 (11)0.0014 (10)0.0002 (9)−0.0016 (10)
C160.0147 (13)0.0153 (14)0.0259 (14)0.0041 (10)0.0019 (10)0.0023 (11)
C170.0132 (12)0.0210 (15)0.0226 (13)0.0035 (11)−0.0014 (10)−0.0012 (11)
C180.0200 (14)0.0161 (15)0.0362 (17)−0.0078 (12)−0.0010 (12)0.0002 (13)
O10.0148 (9)0.0095 (9)0.0269 (10)−0.0020 (7)0.0015 (8)0.0001 (8)
O20.0180 (10)0.0090 (9)0.0268 (10)0.0020 (8)−0.0022 (8)0.0012 (8)
O30.0084 (8)0.0163 (10)0.0239 (10)0.0015 (7)0.0012 (7)−0.0024 (8)
O40.0127 (9)0.0163 (11)0.0277 (10)−0.0044 (8)0.0015 (8)−0.0017 (8)
Br10.02245 (15)0.01443 (15)0.02218 (14)−0.00754 (10)0.00115 (11)−0.00034 (10)
Br20.01823 (14)0.01405 (14)0.02181 (14)0.00654 (10)−0.00010 (10)−0.00210 (10)
Br30.00848 (12)0.02530 (16)0.01724 (13)0.00245 (10)0.00042 (9)−0.00052 (10)
Br40.01199 (13)0.01491 (14)0.02615 (15)−0.00285 (10)0.00015 (10)−0.00184 (10)
Geometric parameters (Å, º) top
C1—C21.391 (4)C10—C151.394 (4)
C1—C61.400 (4)C10—C111.399 (4)
C1—Br11.899 (3)C10—Br31.897 (3)
C2—C31.390 (4)C11—O41.357 (3)
C2—C71.508 (4)C11—C121.392 (4)
C3—C41.400 (4)C12—C131.391 (4)
C3—Br21.898 (3)C12—H120.9300
C4—O11.359 (3)C13—O31.361 (3)
C4—C51.386 (4)C13—C141.397 (4)
C5—C61.389 (4)C14—C151.400 (4)
C5—H50.9300C14—Br41.895 (3)
C6—O21.360 (3)C15—C161.495 (4)
C7—H7A0.9600C16—H16A0.9600
C7—H7B0.9600C16—H16B0.9600
C7—H7C0.9600C16—H16C0.9600
C8—O11.431 (3)C17—O31.433 (4)
C8—H8A0.9600C17—H17A0.9600
C8—H8B0.9600C17—H17B0.9600
C8—H8C0.9600C17—H17C0.9600
C9—O21.436 (3)C18—O41.434 (4)
C9—H9A0.9600C18—H18A0.9600
C9—H9B0.9600C18—H18B0.9600
C9—H9C0.9600C18—H18C0.9600
C2—C1—C6122.4 (2)C11—C10—Br3117.3 (2)
C2—C1—Br1120.2 (2)O4—C11—C12123.8 (3)
C6—C1—Br1117.4 (2)O4—C11—C10117.0 (2)
C3—C2—C1116.8 (2)C12—C11—C10119.2 (2)
C3—C2—C7122.0 (2)C13—C12—C11119.9 (3)
C1—C2—C7121.2 (2)C13—C12—H12120.0
C2—C3—C4122.2 (2)C11—C12—H12120.0
C2—C3—Br2121.0 (2)O3—C13—C12123.4 (2)
C4—C3—Br2116.8 (2)O3—C13—C14116.7 (2)
O1—C4—C5123.4 (2)C12—C13—C14119.9 (2)
O1—C4—C3117.1 (2)C13—C14—C15121.5 (2)
C5—C4—C3119.5 (2)C13—C14—Br4117.40 (19)
C4—C5—C6120.0 (3)C15—C14—Br4121.1 (2)
C4—C5—H5120.0C10—C15—C14117.2 (3)
C6—C5—H5120.0C10—C15—C16120.9 (2)
O2—C6—C5123.6 (2)C14—C15—C16121.9 (2)
O2—C6—C1117.2 (2)C15—C16—H16A109.5
C5—C6—C1119.2 (2)C15—C16—H16B109.5
C2—C7—H7A109.5H16A—C16—H16B109.5
C2—C7—H7B109.5C15—C16—H16C109.5
H7A—C7—H7B109.5H16A—C16—H16C109.5
C2—C7—H7C109.5H16B—C16—H16C109.5
H7A—C7—H7C109.5O3—C17—H17A109.5
H7B—C7—H7C109.5O3—C17—H17B109.5
O1—C8—H8A109.5H17A—C17—H17B109.5
O1—C8—H8B109.5O3—C17—H17C109.5
H8A—C8—H8B109.5H17A—C17—H17C109.5
O1—C8—H8C109.5H17B—C17—H17C109.5
H8A—C8—H8C109.5O4—C18—H18A109.5
H8B—C8—H8C109.5O4—C18—H18B109.5
O2—C9—H9A109.5H18A—C18—H18B109.5
O2—C9—H9B109.5O4—C18—H18C109.5
H9A—C9—H9B109.5H18A—C18—H18C109.5
O2—C9—H9C109.5H18B—C18—H18C109.5
H9A—C9—H9C109.5C4—O1—C8117.5 (2)
H9B—C9—H9C109.5C6—O2—C9117.2 (2)
C15—C10—C11122.3 (2)C13—O3—C17117.4 (2)
C15—C10—Br3120.4 (2)C11—O4—C18117.1 (2)
C6—C1—C2—C30.5 (4)O4—C11—C12—C13179.5 (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—O3179.8 (2)
Br1—C1—C2—C70.6 (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—C4179.3 (2)C12—C13—C14—C150.4 (4)
C1—C2—C3—Br2179.30 (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—O10.8 (3)Br3—C10—C15—C14179.08 (18)
C2—C3—C4—C50.7 (4)C11—C10—C15—C16179.5 (2)
Br2—C3—C4—C5−179.16 (19)Br3—C10—C15—C16−0.6 (3)
O1—C4—C5—C6179.3 (2)C13—C14—C15—C100.1 (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—C16179.8 (2)
C4—C5—C6—C10.7 (4)Br4—C14—C15—C160.2 (3)
C2—C1—C6—O2179.4 (2)C5—C4—O1—C83.2 (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—C97.2 (4)
Br1—C1—C6—C5179.45 (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—O41.2 (3)C14—C13—O3—C17174.8 (2)
C15—C10—C11—C120.9 (4)C12—C11—O4—C180.0 (4)
Br3—C10—C11—C12−178.96 (19)C10—C11—O4—C18179.9 (2)

Experimental details

Crystal data
Chemical formulaC9H10Br2O2
Mr309.99
Crystal system, space groupMonoclinic, P21/c
Temperature (K)446
a, b, c (Å)8.7653 (2), 16.4434 (3), 13.8895 (3)
β (°) 91.715 (1)
V (Å3)2001.02 (7)
Z8
Radiation typeMo Kα
µ (mm−1)8.07
Crystal size (mm)0.55 × 0.25 × 0.10
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.095, 0.499
No. of measured, independent and
observed [I > 2σ(I)] reflections		36582, 4979, 4447
Rint0.037
(sin θ/λ)max (Å−1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.076, 1.04
No. of reflections4979
No. of parameters241
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.79, −0.69

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SAINT-Plus and XPREP (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

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

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.  CSD CrossRef Web of Science Google Scholar
 First citationBruker (2008). APEX2, SAINT-Plus and SADABS. BrukerAXS Inc, Madison, Wisconsin, USA.  Google Scholar
 First citationCukiernik, F. D., Zelcer, A., Garland, M. T. & Baggio, R. (2008). Acta Cryst. C64, o604–o608.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationSaeed, A., Rafique, H., Simpson, J. & Ashraf, Z. (2010). Acta Cryst. E66, o982–o983.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2062
https://doi.org/10.1107/S1600536812025767
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