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

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ISSN: 2056-9890

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

aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 19 March 2009; accepted 23 March 2009; online 28 March 2009)

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[Yordanov, A. T., Mague, J. T. & Roundhill, M. D. (1995a). Inorg. Chem. 34, 5804-5087.],b[Yordanov, A. T., Mague, J. T. & Roundhill, M. D. (1995b). Inorg. Chim. Acta, 240, 441-446.]).

[Scheme 1]

Experimental

Crystal data
  • C21H26Br2O2

  • Mr = 470.24

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.358, Tmax = 0.738

  • 18780 measured reflections

  • 4618 independent reflections

  • 3627 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the structure of bis[2-(3-bromopropoxy)-5-tert-butylphenyl]methane, see: Yordanov et al. (1995a,b). [The scheme shows 2-bromoethoxy; please revise]

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of C21H26O2Br2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Bis[2-(3-bromopropoxy)-5-methylphenyl]methane top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
4618 independent reflections
Radiation source: fine-focus sealed tube3627 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.358, Tmax = 0.738k = 1515
18780 measured reflectionsl = 1818
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.01 w = 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
Crystal data top
C21H26Br2O2V = 2010.16 (6) Å3
Mr = 470.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.0054 (2) ŵ = 4.04 mm1
b = 11.9336 (2) ÅT = 423 K
c = 14.2827 (2) Å0.32 × 0.26 × 0.08 mm
β = 100.777 (1)°
Data collection top
Bruker SMART APEX
diffractometer
4618 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3627 reflections with I > 2σ(I)
Tmin = 0.358, Tmax = 0.738Rint = 0.046
18780 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.01Δρmax = 0.48 e Å3
4618 reflectionsΔρmin = 0.62 e Å3
228 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.89529 (2)0.57379 (2)0.328900 (19)0.03798 (9)
Br20.01238 (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) top
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, º) top
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—C13109.0 (2)
C4—O1—C3—C2170.44 (18)C9—C11—C12—C1774.4 (3)
C1—C2—C3—O162.5 (2)C17—C12—C13—C140.2 (3)
C3—O1—C4—C514.2 (3)C11—C12—C13—C14176.9 (2)
C3—O1—C4—C9167.37 (18)C12—C13—C14—C150.7 (3)
O1—C4—C5—C6177.6 (2)C12—C13—C14—C18179.7 (2)
C9—C4—C5—C60.8 (3)C13—C14—C15—C160.7 (3)
C4—C5—C6—C70.7 (3)C18—C14—C15—C16179.8 (2)
C5—C6—C7—C80.3 (3)C14—C15—C16—C170.3 (4)
C5—C6—C7—C10179.2 (2)C19—O2—C17—C1610.0 (3)
C6—C7—C8—C90.2 (3)C19—O2—C17—C12169.29 (19)
C10—C7—C8—C9179.6 (2)C15—C16—C17—O2179.4 (2)
C7—C8—C9—C40.1 (3)C15—C16—C17—C120.2 (3)
C7—C8—C9—C11177.87 (19)C13—C12—C17—O2179.52 (18)
O1—C4—C9—C8178.16 (18)C11—C12—C17—O22.8 (3)
C5—C4—C9—C80.4 (3)C13—C12—C17—C160.2 (3)
O1—C4—C9—C110.2 (3)C11—C12—C17—C16176.5 (2)
C5—C4—C9—C11178.35 (19)C17—O2—C19—C20175.85 (18)
C8—C9—C11—C12113.2 (2)O2—C19—C20—C2169.0 (3)
C4—C9—C11—C1268.9 (3)C19—C20—C21—Br2176.17 (16)

Experimental details

Crystal data
Chemical formulaC21H26Br2O2
Mr470.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)423
a, b, c (Å)12.0054 (2), 11.9336 (2), 14.2827 (2)
β (°) 100.777 (1)
V3)2010.16 (6)
Z4
Radiation typeMo Kα
µ (mm1)4.04
Crystal size (mm)0.32 × 0.26 × 0.08
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.358, 0.738
No. of measured, independent and
observed [I > 2σ(I)] reflections
18780, 4618, 3627
Rint0.046
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.079, 1.01
No. of reflections4618
No. of parameters228
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.62

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationYordanov, A. T., Mague, J. T. & Roundhill, M. D. (1995a). Inorg. Chem. 34, 5804–5087.  CSD CrossRef Web of Science Google Scholar
First citationYordanov, A. T., Mague, J. T. & Roundhill, M. D. (1995b). Inorg. Chim. Acta, 240, 441–446.  CSD CrossRef CAS Web of Science Google Scholar

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