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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o907.
Published online 2009 March 28. doi:  10.1107/S1600536809010587
PMCID: PMC2968948

Bis[2-(3-bromo­prop­oxy)-5-methyl­phen­yl]methane

Abstract

The title mol­ecule, C21H26Br2O2, is a substituted diphenyl­methane derivative whose angle at the methyl­ene carbon is 115.0 (2)°.

Related literature

For the structure of bis­[2-(3-bromo­prop­oxy)-5-tert-butyl­phen­yl]methane, see: Yordanov et al. (1995a [triangle],b [triangle]).

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Object name is e-65-0o907-scheme1.jpg

Experimental

Crystal data

  • C21H26Br2O2
  • M r = 470.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o907-efi1.jpg
  • a = 12.0054 (2) Å
  • b = 11.9336 (2) Å
  • c = 14.2827 (2) Å
  • β = 100.777 (1)°
  • V = 2010.16 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.04 mm−1
  • T = 423 K
  • 0.32 × 0.26 × 0.08 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.358, T max = 0.738
  • 18780 measured reflections
  • 4618 independent reflections
  • 3627 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.079
  • S = 1.01
  • 4618 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010587/tk2401sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010587/tk2401Isup2.hkl

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

Acknowledgments

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Potassium carbonate (414 mg, 3 mmol) and 2,2'-methylenebis(4-methylphenol) (228 mg, 1 mmol) in acetone (15 ml) were treated with 1,3-dibromopropane (1.05 g, 5 mmol) at 323 K for 3 h. The solvent was removed under reduced pressure and the residue was dissolved in a mixture of water (50 ml) and dichloromethane (50 ml). The two phases were separated and the aqueous layer extracted with dichloromethane. The dichloromethane solution was dried and the solvent allowed to evaporate slowly to give colorless crystals (182 mg, 80% yield).

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.99 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2 to 1.5U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) plot of C21H26O2Br2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C21H26Br2O2F(000) = 952
Mr = 470.24Dx = 1.554 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5910 reflections
a = 12.0054 (2) Åθ = 2.4–28.1°
b = 11.9336 (2) ŵ = 4.04 mm1
c = 14.2827 (2) ÅT = 423 K
β = 100.777 (1)°Plate, colorless
V = 2010.16 (6) Å30.32 × 0.26 × 0.08 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4618 independent reflections
Radiation source: fine-focus sealed tube3627 reflections with I > 2σ(I)
graphiteRint = 0.046
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.358, Tmax = 0.738k = −15→15
18780 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.034P)2 + 1.182P] where P = (Fo2 + 2Fc2)/3
4618 reflections(Δ/σ)max = 0.001
228 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = −0.62 e Å3

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

xyzUiso*/Ueq
Br10.89529 (2)0.57379 (2)0.328900 (19)0.03798 (9)
Br2−0.01238 (2)0.17450 (2)0.39338 (2)0.04079 (9)
O10.61771 (14)0.43666 (12)0.39928 (11)0.0255 (3)
O20.38760 (13)0.14783 (13)0.48653 (10)0.0244 (3)
C10.8608 (2)0.4599 (2)0.41785 (17)0.0291 (5)
H1A0.81990.39700.38140.035*
H1B0.93250.43030.45520.035*
C20.7896 (2)0.5065 (2)0.48479 (16)0.0290 (5)
H2A0.78510.44990.53470.035*
H2B0.82800.57340.51670.035*
C30.6711 (2)0.53852 (19)0.43790 (17)0.0277 (5)
H3A0.62970.57140.48510.033*
H3B0.67280.59400.38660.033*
C40.5034 (2)0.43657 (19)0.36428 (15)0.0229 (5)
C50.4379 (2)0.5323 (2)0.34459 (16)0.0283 (5)
H50.47120.60420.35750.034*
C60.3231 (2)0.5226 (2)0.30578 (17)0.0306 (5)
H60.27890.58860.29180.037*
C70.2715 (2)0.4188 (2)0.28700 (15)0.0270 (5)
C80.3394 (2)0.32366 (19)0.30820 (15)0.0226 (5)
H80.30550.25190.29600.027*
C90.45441 (19)0.32978 (18)0.34640 (14)0.0206 (4)
C100.1470 (2)0.4079 (2)0.24627 (18)0.0360 (6)
H10A0.12410.46750.19940.054*
H10B0.10350.41430.29770.054*
H10C0.13230.33480.21520.054*
C110.52599 (19)0.22530 (18)0.36524 (14)0.0208 (4)
H11A0.59100.23230.33200.025*
H11B0.48010.16050.33720.025*
C120.57131 (19)0.20078 (17)0.46953 (14)0.0198 (4)
C130.6855 (2)0.21308 (18)0.50828 (15)0.0231 (5)
H130.73480.24100.46880.028*
C140.7311 (2)0.18620 (19)0.60292 (16)0.0257 (5)
C150.6577 (2)0.1448 (2)0.65809 (16)0.0281 (5)
H150.68670.12510.72250.034*
C160.5428 (2)0.1311 (2)0.62258 (16)0.0269 (5)
H160.49410.10280.66230.032*
C170.49961 (19)0.15936 (17)0.52813 (15)0.0213 (5)
C180.8558 (2)0.2004 (2)0.64178 (18)0.0346 (6)
H18A0.89950.17540.59410.052*
H18B0.87710.15560.69980.052*
H18C0.87220.27960.65670.052*
C190.3171 (2)0.0874 (2)0.53991 (17)0.0278 (5)
H19A0.31260.12800.59960.033*
H19B0.34920.01210.55680.033*
C200.2007 (2)0.07720 (19)0.47873 (18)0.0290 (5)
H20A0.20740.04620.41570.035*
H20B0.15450.02460.50910.035*
C210.1424 (2)0.1886 (2)0.46541 (18)0.0298 (5)
H21A0.18600.23960.43110.036*
H21B0.14040.22190.52860.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03685 (16)0.04009 (16)0.04195 (15)−0.00652 (11)0.02015 (12)−0.00002 (11)
Br20.03188 (16)0.04527 (17)0.04445 (16)0.00566 (12)0.00512 (12)−0.00249 (12)
O10.0253 (9)0.0198 (8)0.0330 (8)−0.0047 (6)0.0098 (7)−0.0048 (6)
O20.0219 (8)0.0286 (9)0.0237 (8)−0.0027 (7)0.0068 (7)0.0033 (6)
C10.0291 (13)0.0257 (12)0.0311 (12)−0.0052 (10)0.0018 (10)−0.0029 (10)
C20.0379 (14)0.0246 (13)0.0247 (11)−0.0104 (10)0.0060 (10)−0.0057 (9)
C30.0350 (14)0.0217 (12)0.0297 (12)−0.0072 (10)0.0149 (10)−0.0062 (9)
C40.0262 (12)0.0245 (12)0.0207 (10)0.0005 (9)0.0111 (9)0.0017 (9)
C50.0365 (14)0.0224 (12)0.0296 (12)0.0019 (10)0.0152 (10)0.0022 (9)
C60.0384 (15)0.0274 (13)0.0290 (12)0.0102 (11)0.0141 (11)0.0075 (10)
C70.0273 (13)0.0347 (13)0.0203 (10)0.0050 (10)0.0080 (9)0.0023 (9)
C80.0250 (12)0.0248 (11)0.0191 (10)−0.0009 (9)0.0067 (9)0.0006 (9)
C90.0251 (12)0.0225 (11)0.0156 (9)0.0013 (9)0.0079 (8)0.0013 (8)
C100.0287 (14)0.0459 (16)0.0325 (13)0.0088 (11)0.0033 (11)0.0040 (11)
C110.0239 (12)0.0205 (11)0.0191 (10)−0.0006 (9)0.0065 (9)−0.0022 (8)
C120.0242 (12)0.0151 (10)0.0203 (10)0.0019 (8)0.0050 (9)−0.0028 (8)
C130.0258 (12)0.0177 (11)0.0264 (11)−0.0024 (9)0.0061 (9)−0.0017 (9)
C140.0265 (13)0.0204 (11)0.0278 (11)0.0004 (9)−0.0009 (9)−0.0054 (9)
C150.0332 (14)0.0296 (13)0.0189 (10)0.0048 (10)−0.0015 (10)0.0001 (9)
C160.0320 (14)0.0266 (12)0.0238 (11)0.0012 (10)0.0097 (10)0.0019 (9)
C170.0227 (12)0.0183 (11)0.0227 (10)0.0008 (9)0.0042 (9)−0.0014 (8)
C180.0270 (14)0.0361 (15)0.0370 (13)−0.0005 (11)−0.0037 (11)−0.0039 (11)
C190.0281 (13)0.0241 (12)0.0338 (12)−0.0028 (10)0.0125 (10)0.0036 (10)
C200.0259 (13)0.0224 (12)0.0412 (13)−0.0036 (10)0.0124 (10)−0.0024 (10)
C210.0314 (14)0.0244 (12)0.0351 (12)−0.0001 (10)0.0096 (11)−0.0038 (10)

Geometric parameters (Å, °)

Br1—C11.957 (2)C10—H10B0.9800
Br2—C211.956 (3)C10—H10C0.9800
O1—C41.369 (3)C11—C121.516 (3)
O1—C31.436 (3)C11—H11A0.9900
O2—C171.372 (3)C11—H11B0.9900
O2—C191.435 (3)C12—C131.387 (3)
C1—C21.503 (3)C12—C171.398 (3)
C1—H1A0.9900C13—C141.398 (3)
C1—H1B0.9900C13—H130.9500
C2—C31.503 (4)C14—C151.379 (3)
C2—H2A0.9900C14—C181.506 (3)
C2—H2B0.9900C15—C161.388 (3)
C3—H3A0.9900C15—H150.9500
C3—H3B0.9900C16—C171.393 (3)
C4—C51.386 (3)C16—H160.9500
C4—C91.407 (3)C18—H18A0.9800
C5—C61.391 (4)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.389 (4)C19—C201.509 (3)
C6—H60.9500C19—H19A0.9900
C7—C81.397 (3)C19—H19B0.9900
C7—C101.505 (3)C20—C211.497 (3)
C8—C91.388 (3)C20—H20A0.9900
C8—H80.9500C20—H20B0.9900
C9—C111.510 (3)C21—H21A0.9900
C10—H10A0.9800C21—H21B0.9900
C4—O1—C3119.08 (18)C12—C11—H11A108.5
C17—O2—C19116.61 (17)C9—C11—H11B108.5
C2—C1—Br1111.78 (17)C12—C11—H11B108.5
C2—C1—H1A109.3H11A—C11—H11B107.5
Br1—C1—H1A109.3C13—C12—C17118.14 (19)
C2—C1—H1B109.3C13—C12—C11121.2 (2)
Br1—C1—H1B109.3C17—C12—C11120.6 (2)
H1A—C1—H1B107.9C12—C13—C14122.8 (2)
C3—C2—C1114.44 (19)C12—C13—H13118.6
C3—C2—H2A108.6C14—C13—H13118.6
C1—C2—H2A108.6C15—C14—C13117.3 (2)
C3—C2—H2B108.6C15—C14—C18121.8 (2)
C1—C2—H2B108.6C13—C14—C18120.9 (2)
H2A—C2—H2B107.6C14—C15—C16122.1 (2)
O1—C3—C2105.84 (19)C14—C15—H15118.9
O1—C3—H3A110.6C16—C15—H15118.9
C2—C3—H3A110.6C15—C16—C17119.3 (2)
O1—C3—H3B110.6C15—C16—H16120.3
C2—C3—H3B110.6C17—C16—H16120.3
H3A—C3—H3B108.7O2—C17—C16123.5 (2)
O1—C4—C5124.4 (2)O2—C17—C12116.07 (18)
O1—C4—C9115.06 (19)C16—C17—C12120.4 (2)
C5—C4—C9120.5 (2)C14—C18—H18A109.5
C4—C5—C6119.7 (2)C14—C18—H18B109.5
C4—C5—H5120.2H18A—C18—H18B109.5
C6—C5—H5120.2C14—C18—H18C109.5
C7—C6—C5121.6 (2)H18A—C18—H18C109.5
C7—C6—H6119.2H18B—C18—H18C109.5
C5—C6—H6119.2O2—C19—C20107.90 (19)
C6—C7—C8117.5 (2)O2—C19—H19A110.1
C6—C7—C10121.8 (2)C20—C19—H19A110.1
C8—C7—C10120.7 (2)O2—C19—H19B110.1
C9—C8—C7122.7 (2)C20—C19—H19B110.1
C9—C8—H8118.7H19A—C19—H19B108.4
C7—C8—H8118.7C21—C20—C19111.2 (2)
C8—C9—C4118.1 (2)C21—C20—H20A109.4
C8—C9—C11121.2 (2)C19—C20—H20A109.4
C4—C9—C11120.7 (2)C21—C20—H20B109.4
C7—C10—H10A109.5C19—C20—H20B109.4
C7—C10—H10B109.5H20A—C20—H20B108.0
H10A—C10—H10B109.5C20—C21—Br2111.45 (17)
C7—C10—H10C109.5C20—C21—H21A109.3
H10A—C10—H10C109.5Br2—C21—H21A109.3
H10B—C10—H10C109.5C20—C21—H21B109.3
C9—C11—C12114.98 (17)Br2—C21—H21B109.3
C9—C11—H11A108.5H21A—C21—H21B108.0
Br1—C1—C2—C367.6 (2)C9—C11—C12—C13−109.0 (2)
C4—O1—C3—C2170.44 (18)C9—C11—C12—C1774.4 (3)
C1—C2—C3—O162.5 (2)C17—C12—C13—C14−0.2 (3)
C3—O1—C4—C514.2 (3)C11—C12—C13—C14−176.9 (2)
C3—O1—C4—C9−167.37 (18)C12—C13—C14—C150.7 (3)
O1—C4—C5—C6177.6 (2)C12—C13—C14—C18179.7 (2)
C9—C4—C5—C6−0.8 (3)C13—C14—C15—C16−0.7 (3)
C4—C5—C6—C70.7 (3)C18—C14—C15—C16−179.8 (2)
C5—C6—C7—C8−0.3 (3)C14—C15—C16—C170.3 (4)
C5—C6—C7—C10179.2 (2)C19—O2—C17—C16−10.0 (3)
C6—C7—C8—C9−0.2 (3)C19—O2—C17—C12169.29 (19)
C10—C7—C8—C9−179.6 (2)C15—C16—C17—O2179.4 (2)
C7—C8—C9—C40.1 (3)C15—C16—C17—C120.2 (3)
C7—C8—C9—C11−177.87 (19)C13—C12—C17—O2−179.52 (18)
O1—C4—C9—C8−178.16 (18)C11—C12—C17—O2−2.8 (3)
C5—C4—C9—C80.4 (3)C13—C12—C17—C16−0.2 (3)
O1—C4—C9—C11−0.2 (3)C11—C12—C17—C16176.5 (2)
C5—C4—C9—C11178.35 (19)C17—O2—C19—C20−175.85 (18)
C8—C9—C11—C12−113.2 (2)O2—C19—C20—C21−69.0 (3)
C4—C9—C11—C1268.9 (3)C19—C20—C21—Br2−176.17 (16)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2401).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Yordanov, A. T., Mague, J. T. & Roundhill, M. D. (1995a). Inorg. Chem.34, 5804–5087.
  • Yordanov, A. T., Mague, J. T. & Roundhill, M. D. (1995b). Inorg. Chim. Acta, 240, 441–446.

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