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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o925.
Published online 2008 April 26. doi:  10.1107/S1600536808011665
PMCID: PMC2961170

2,10-Dibromo-6-isobutyl-6-methyl­dibenzo[d,f][1,3]dioxepine

Abstract

In the crystal structure of the title compound, C18H18Br2O2, the two benzene rings of the bridged biphenyl unit are twisted by 38.0 (1)°.

Related literature

For the synthesis of the title compound, see: Zhang et al. (2003 [triangle]).

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Object name is e-64-0o925-scheme1.jpg

Experimental

Crystal data

  • C18H18Br2O2
  • M r = 426.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o925-efi1.jpg
  • a = 8.3372 (9) Å
  • b = 19.362 (2) Å
  • c = 10.8066 (16) Å
  • β = 100.803 (5)°
  • V = 1713.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 4.74 mm−1
  • T = 193 (2) K
  • 0.13 × 0.12 × 0.12 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.587, T max = 0.607 (expected range = 0.547–0.567)
  • 7425 measured reflections
  • 3924 independent reflections
  • 2495 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.052
  • S = 0.85
  • 3924 reflections
  • 202 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.51 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97 .

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011665/nc2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011665/nc2099Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the National Science Foundation of China (20125421, 90101026, 50303007 and 60207003) and the Ministry of Science and Technology of China (2002CB6134003 and 2003CB3147032).

supplementary crystallographic information

Comment

Recently we have reported on the synthesis of the title compound 2,10-Dibromo -6-isobutyl-6-methyl-Dibenzo [d,f][1,3] Dioxepine (Zhang et al. 2003). Herein we present the crysal structure of this compound. In the crystal structure of the title compound the two benzene rings of the bridged biphenyl unit are twisted by 38.0 (1)° and the 7-membered ring is in a boat conformation.

Experimental

The title compound was synthesized as described previously (Zhang et al. 2003). Single crystals were obtained by slow evaporation of the solvent from a methanol solution at room temperature.

Refinement

All H atoms were positioned with idealized geometry and refined isotropic with Uiso(H) = 1.5Ueq(C) for methyl and Uiso(H) = 1.2Ueq(C)for all other H atoms using a riding model with C—H = 0.97 Å for methyl and C—H = 0.93 Å for all other H atoms.

Figures

Fig. 1.
Crystal structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

Crystal data

C18H18Br2O2F000 = 848
Mr = 426.14Dx = 1.652 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12167 reflections
a = 8.3372 (9) Åθ = 2.1–54.9º
b = 19.362 (2) ŵ = 4.74 mm1
c = 10.8066 (16) ÅT = 193 (2) K
β = 100.803 (5)ºBlock, colorless
V = 1713.5 (4) Å30.13 × 0.12 × 0.12 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer3924 independent reflections
Radiation source: fine-focus sealed tube2495 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 193(2) Kθmax = 27.5º
ω scansθmin = 2.1º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −10→10
Tmin = 0.587, Tmax = 0.607k = −25→25
7425 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.052  w = 1/[σ2(Fo2) + (0.0206P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.001
3924 reflectionsΔρmax = 0.41 e Å3
202 parametersΔρmin = −0.51 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

xyzUiso*/Ueq
Br11.32353 (3)0.596022 (13)0.68875 (3)0.03946 (9)
Br21.32322 (4)0.994048 (14)0.80855 (4)0.06258 (12)
C11.0296 (3)0.70180 (11)0.9608 (2)0.0219 (5)
C21.0540 (3)0.63147 (11)0.9678 (2)0.0273 (6)
H21.01000.60511.02760.033*
C31.1424 (3)0.59896 (11)0.8880 (2)0.0294 (6)
H31.15960.55040.89210.035*
C41.2052 (3)0.63899 (12)0.8022 (2)0.0264 (6)
C51.1833 (3)0.70927 (11)0.7948 (2)0.0238 (5)
H51.22830.73540.73530.029*
C61.0946 (3)0.74206 (11)0.8752 (2)0.0220 (5)
C70.9182 (3)0.84461 (11)0.8840 (2)0.0240 (5)
C81.0681 (3)0.81720 (11)0.8698 (2)0.0226 (5)
C91.1879 (3)0.86301 (12)0.8475 (2)0.0305 (6)
H91.29140.84600.83700.037*
C101.1573 (3)0.93303 (12)0.8403 (2)0.0329 (7)
C111.0099 (3)0.95998 (11)0.8559 (2)0.0333 (6)
H110.99141.00840.85170.040*
C120.8886 (3)0.91495 (11)0.8779 (2)0.0297 (6)
H120.78560.93240.88870.036*
C130.7930 (3)0.76216 (11)1.0048 (2)0.0231 (5)
C140.7645 (3)0.81026 (11)1.1085 (2)0.0304 (6)
H14A0.77260.78431.18730.046*
H14B0.65540.83081.08600.046*
H14C0.84690.84701.11950.046*
C150.6684 (3)0.70529 (11)0.9684 (2)0.0239 (5)
H15A0.70270.67670.90200.029*
H15B0.56220.72670.93160.029*
C160.6434 (3)0.65766 (12)1.0774 (2)0.0271 (6)
H160.74520.65921.14310.032*
C170.6163 (3)0.58315 (12)1.0329 (2)0.0404 (7)
H17A0.60300.55381.10410.061*
H17B0.71060.56730.99840.061*
H17C0.51770.58040.96740.061*
C180.5010 (3)0.68121 (13)1.1386 (2)0.0414 (7)
H18A0.39890.67841.07670.062*
H18B0.51930.72901.16770.062*
H18C0.49380.65121.21040.062*
O10.95321 (18)0.73412 (7)1.04861 (13)0.0232 (4)
O20.78958 (17)0.79979 (7)0.88965 (14)0.0243 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.03994 (16)0.03630 (15)0.04601 (17)0.00641 (13)0.01797 (13)−0.00815 (14)
Br20.0675 (2)0.03245 (16)0.1003 (3)−0.01841 (15)0.0480 (2)−0.00512 (17)
C10.0173 (13)0.0274 (13)0.0206 (13)0.0013 (10)0.0024 (11)0.0006 (10)
C20.0242 (13)0.0273 (13)0.0309 (15)0.0009 (11)0.0066 (12)0.0070 (11)
C30.0267 (13)0.0213 (12)0.0391 (16)0.0033 (11)0.0029 (12)0.0019 (12)
C40.0170 (13)0.0304 (13)0.0316 (15)0.0042 (10)0.0039 (12)−0.0069 (11)
C50.0198 (12)0.0276 (13)0.0243 (14)0.0006 (10)0.0050 (11)0.0011 (11)
C60.0178 (13)0.0247 (12)0.0225 (13)−0.0005 (10)0.0016 (11)−0.0007 (10)
C70.0244 (14)0.0260 (13)0.0212 (14)−0.0015 (10)0.0030 (11)−0.0009 (10)
C80.0283 (13)0.0207 (11)0.0205 (13)−0.0008 (10)0.0083 (11)−0.0004 (10)
C90.0306 (15)0.0298 (14)0.0338 (17)−0.0028 (11)0.0131 (14)−0.0036 (11)
C100.0423 (16)0.0252 (13)0.0362 (17)−0.0089 (12)0.0203 (14)−0.0007 (11)
C110.0458 (18)0.0205 (12)0.0354 (16)0.0023 (12)0.0122 (14)0.0013 (11)
C120.0313 (14)0.0279 (14)0.0303 (15)0.0064 (11)0.0067 (12)0.0034 (11)
C130.0245 (13)0.0279 (12)0.0167 (13)0.0044 (11)0.0032 (11)0.0033 (10)
C140.0294 (14)0.0320 (14)0.0304 (16)0.0018 (12)0.0073 (12)−0.0052 (12)
C150.0207 (13)0.0280 (12)0.0222 (13)0.0017 (10)0.0020 (11)−0.0004 (11)
C160.0215 (13)0.0352 (14)0.0237 (14)−0.0039 (11)0.0025 (11)0.0023 (11)
C170.0423 (17)0.0333 (15)0.0468 (18)−0.0035 (13)0.0116 (14)0.0074 (13)
C180.0331 (16)0.0539 (17)0.0408 (18)−0.0094 (13)0.0163 (14)−0.0011 (14)
O10.0193 (9)0.0305 (9)0.0197 (9)0.0023 (7)0.0033 (7)0.0001 (7)
O20.0226 (9)0.0266 (9)0.0230 (9)−0.0009 (7)0.0028 (8)0.0043 (7)

Geometric parameters (Å, °)

Br1—C41.903 (2)C11—H110.9500
Br2—C101.898 (2)C12—H120.9500
C1—C21.377 (3)C13—O11.437 (3)
C1—O11.387 (2)C13—O21.438 (2)
C1—C61.395 (3)C13—C141.510 (3)
C2—C31.386 (3)C13—C151.515 (3)
C2—H20.9500C14—H14A0.9800
C3—C41.384 (3)C14—H14B0.9800
C3—H30.9500C14—H14C0.9800
C4—C51.373 (3)C15—C161.541 (3)
C5—C61.394 (3)C15—H15A0.9900
C5—H50.9500C15—H15B0.9900
C6—C81.471 (3)C16—C171.524 (3)
C7—C121.384 (3)C16—C181.532 (3)
C7—O21.390 (2)C16—H161.0000
C7—C81.393 (3)C17—H17A0.9800
C8—C91.390 (3)C17—H17B0.9800
C9—C101.379 (3)C17—H17C0.9800
C9—H90.9500C18—H18A0.9800
C10—C111.375 (3)C18—H18B0.9800
C11—C121.390 (3)C18—H18C0.9800
C2—C1—O1119.39 (18)O1—C13—C14104.76 (18)
C2—C1—C6121.15 (19)O2—C13—C14110.46 (17)
O1—C1—C6119.15 (19)O1—C13—C15111.15 (17)
C1—C2—C3120.3 (2)O2—C13—C15103.98 (18)
C1—C2—H2119.8C14—C13—C15116.49 (17)
C3—C2—H2119.8C13—C14—H14A109.5
C4—C3—C2118.3 (2)C13—C14—H14B109.5
C4—C3—H3120.8H14A—C14—H14B109.5
C2—C3—H3120.8C13—C14—H14C109.5
C5—C4—C3122.06 (19)H14A—C14—H14C109.5
C5—C4—Br1118.37 (16)H14B—C14—H14C109.5
C3—C4—Br1119.57 (16)C13—C15—C16114.87 (19)
C4—C5—C6119.70 (19)C13—C15—H15A108.6
C4—C5—H5120.2C16—C15—H15A108.6
C6—C5—H5120.2C13—C15—H15B108.6
C5—C6—C1118.4 (2)C16—C15—H15B108.6
C5—C6—C8121.27 (18)H15A—C15—H15B107.5
C1—C6—C8120.31 (18)C17—C16—C18109.68 (19)
C12—C7—O2119.0 (2)C17—C16—C15111.01 (19)
C12—C7—C8121.7 (2)C18—C16—C15112.25 (19)
O2—C7—C8118.87 (18)C17—C16—H16107.9
C9—C8—C7117.69 (19)C18—C16—H16107.9
C9—C8—C6122.05 (19)C15—C16—H16107.9
C7—C8—C6120.24 (18)C16—C17—H17A109.5
C10—C9—C8120.4 (2)C16—C17—H17B109.5
C10—C9—H9119.8H17A—C17—H17B109.5
C8—C9—H9119.8C16—C17—H17C109.5
C11—C10—C9121.8 (2)H17A—C17—H17C109.5
C11—C10—Br2118.97 (17)H17B—C17—H17C109.5
C9—C10—Br2119.27 (18)C16—C18—H18A109.5
C10—C11—C12118.6 (2)C16—C18—H18B109.5
C10—C11—H11120.7H18A—C18—H18B109.5
C12—C11—H11120.7C16—C18—H18C109.5
C7—C12—C11119.8 (2)H18A—C18—H18C109.5
C7—C12—H12120.1H18B—C18—H18C109.5
C11—C12—H12120.1C1—O1—C13117.59 (17)
O1—C13—O2110.04 (15)C7—O2—C13117.64 (17)
O1—C1—C2—C3−174.4 (2)C8—C9—C10—C110.6 (4)
C6—C1—C2—C3−0.9 (4)C8—C9—C10—Br2−179.60 (18)
C1—C2—C3—C40.1 (4)C9—C10—C11—C12−0.8 (4)
C2—C3—C4—C50.5 (4)Br2—C10—C11—C12179.40 (19)
C2—C3—C4—Br1−178.75 (18)O2—C7—C12—C11−171.7 (2)
C3—C4—C5—C6−0.4 (4)C8—C7—C12—C110.6 (4)
Br1—C4—C5—C6178.88 (17)C10—C11—C12—C70.2 (4)
C4—C5—C6—C1−0.4 (3)O1—C13—C15—C1663.4 (2)
C4—C5—C6—C8−179.8 (2)O2—C13—C15—C16−178.25 (16)
C2—C1—C6—C51.0 (4)C14—C13—C15—C16−56.5 (3)
O1—C1—C6—C5174.5 (2)C13—C15—C16—C17−142.7 (2)
C2—C1—C6—C8−179.6 (2)C13—C15—C16—C1894.2 (2)
O1—C1—C6—C8−6.0 (3)C2—C1—O1—C13−111.5 (2)
C12—C7—C8—C9−0.8 (4)C6—C1—O1—C1374.8 (3)
O2—C7—C8—C9171.5 (2)O2—C13—O1—C1−45.4 (2)
C12—C7—C8—C6−179.2 (2)C14—C13—O1—C1−164.10 (17)
O2—C7—C8—C6−6.8 (3)C15—C13—O1—C169.3 (2)
C5—C6—C8—C9−37.5 (4)C12—C7—O2—C13−112.0 (2)
C1—C6—C8—C9143.1 (2)C8—C7—O2—C1375.5 (2)
C5—C6—C8—C7140.8 (2)O1—C13—O2—C7−45.3 (2)
C1—C6—C8—C7−38.6 (3)C14—C13—O2—C769.9 (2)
C7—C8—C9—C100.2 (4)C15—C13—O2—C7−164.38 (16)
C6—C8—C9—C10178.5 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2099).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC and Rigaku (2002). CrystalStructure MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Zhang, H.Q., Mu, S.-C., Zheng, Y., Yang, G-D., Ye, , Ma, Y.-G., Chen, X.-F. & Shen J.-C. (2003). Chin. J. Org. Chem.23, 578–583.

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