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The mol­ecule of the title compound, C20H40Br2, is centrosymmetric and the skeleton has an all-trans conformation including both terminal Br atoms. In the crystal structure, the mol­ecules form a layer in which the long axes of the mol­ecules are inclined to the basal plane of the Br atoms. The layers are arranged in a zigzag manner between the neighboring layers, forming a herringbone motif, just like the smectic CA phase of liquid crystals.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017556/ob6387sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017556/ob6387Isup2.hkl
Contains datablock I

CCDC reference: 248843

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.038
  • wR factor = 0.116
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Coorporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Molecular Structure Coorporation & Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

(I) top
Crystal data top
C20H40Br2F(000) = 460.00
Mr = 440.34Dx = 1.325 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ynCell parameters from 24 reflections
a = 5.482 (4) Åθ = 9.5–15.5°
b = 5.383 (2) ŵ = 4.61 mm1
c = 37.412 (2) ÅT = 296 K
β = 91.50 (2)°Plate, colorless
V = 1103.6 (9) Å30.59 × 0.47 × 0.04 mm
Z = 2
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.028
ω–2θ scansθmax = 70.1°
Absorption correction: integration
(NUMABS; Higashi, 1997)
h = 16
Tmin = 0.325, Tmax = 0.997k = 06
3004 measured reflectionsl = 4545
2008 independent reflections3 standard reflections every 150 reflections
1667 reflections with F2 > 2σ(F2) intensity decay: 6.8%
Refinement top
Refinement on F2 w = 1/[0.001Fo2 + 5.3σ2(Fo) + 0.52]/(4Fo2)
R[F2 > 2σ(F2)] = 0.038(Δ/σ)max < 0.001
wR(F2) = 0.116Δρmax = 0.38 e Å3
S = 1.00Δρmin = 0.62 e Å3
2008 reflectionsExtinction correction: (Larson, 1970)
121 parametersExtinction coefficient: 21.3 (3)
H-atom parameters constrained
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F2 > -3.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br12.10859 (8)1.11565 (8)0.77760 (1)0.0745 (2)
C11.9280 (8)0.8210 (8)0.7914 (1)0.073 (1)
C21.7723 (7)0.8642 (7)0.8228 (1)0.064 (1)
C31.6346 (7)0.6328 (7)0.83329 (9)0.063 (1)
C41.4761 (8)0.6735 (7)0.8657 (1)0.064 (1)
C51.3358 (7)0.4444 (7)0.87653 (9)0.060 (1)
C61.1766 (7)0.4850 (7)0.90874 (9)0.062 (1)
C71.0317 (7)0.2594 (7)0.91933 (9)0.061 (1)
C80.8758 (7)0.2971 (7)0.95168 (9)0.061 (1)
C90.7299 (7)0.0727 (7)0.96236 (9)0.062 (1)
C100.5733 (7)0.1120 (6)0.99475 (9)0.061 (1)
H11.82820.76830.77160.088*
H22.04140.69360.79750.088*
H31.65610.98900.81660.077*
H41.87080.91900.84250.077*
H51.53510.57870.813630.075*
H61.75080.50760.839290.075*
H71.36060.79920.85970.077*
H81.57600.72740.88540.077*
H91.23520.39080.856950.073*
H101.45120.31840.882470.073*
H111.06450.61450.903000.075*
H121.27780.53410.928500.075*
H130.93020.21120.899560.074*
H141.14430.12990.924860.074*
H150.76320.42650.946100.073*
H160.97750.34590.971400.073*
H170.62830.02340.942660.074*
H180.84210.05670.968070.074*
H190.46120.24180.989210.074*
H200.67430.15941.014610.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0855 (4)0.0635 (3)0.0758 (3)0.0095 (2)0.0281 (2)0.0029 (2)
C10.091 (3)0.064 (2)0.064 (2)0.007 (2)0.027 (2)0.003 (2)
C20.071 (2)0.060 (2)0.060 (2)0.006 (2)0.017 (2)0.001 (2)
C30.072 (2)0.062 (2)0.055 (2)0.009 (2)0.016 (2)0.000 (2)
C40.072 (2)0.061 (2)0.059 (2)0.003 (2)0.017 (2)0.000 (2)
C50.070 (2)0.059 (2)0.053 (2)0.007 (2)0.016 (2)0.001 (2)
C60.071 (2)0.061 (2)0.054 (2)0.007 (2)0.016 (2)0.001 (2)
C70.070 (2)0.062 (2)0.053 (2)0.009 (2)0.016 (2)0.000 (2)
C80.071 (2)0.060 (2)0.053 (2)0.007 (2)0.016 (2)0.002 (2)
C90.073 (2)0.061 (2)0.052 (2)0.005 (2)0.016 (2)0.002 (2)
C100.073 (2)0.060 (2)0.052 (2)0.007 (2)0.017 (2)0.000 (2)
Geometric parameters (Å, º) top
Br1—C11.946 (4)C3—H60.950
C1—C21.489 (5)C4—H70.950
C2—C31.514 (5)C4—H80.95
C3—C41.526 (5)C5—H90.95
C4—C51.514 (5)C5—H100.950
C5—C61.522 (4)C6—H110.950
C6—C71.510 (5)C6—H120.95
C7—C81.514 (4)C7—H130.95
C8—C91.509 (5)C7—H140.950
C9—C101.518 (4)C8—H150.950
C10—C10i1.507 (5)C8—H160.95
C1—H10.95C9—H170.95
C1—H20.950C9—H180.950
C2—H30.950C10—H190.950
C2—H40.95C10—H200.95
C3—H50.95
Br1···Br1ii3.752 (3)Br1···Br1iii3.752 (3)
Br1—C1—C2112.8 (3)C6—C5—H9108.7
C1—C2—C3112.1 (3)C4—C5—H10107.7
C2—C3—C4112.7 (3)C6—C5—H10108.0
C3—C4—C5113.5 (3)H9—C5—H10109.5
C4—C5—C6113.6 (3)C5—C6—H11107.9
C5—C6—C7114.1 (3)C7—C6—H11107.9
C6—C7—C8114.4 (3)C5—C6—H12108.7
C7—C8—C9114.7 (3)C7—C6—H12108.7
C8—C9—C10114.5 (3)H11—C6—H12109.5
C9—C10—C10i114.4 (3)C6—C7—H13108.5
C2—C1—H1109.2C8—C7—H13109.1
Br1—C1—H2108.6C6—C7—H14107.7
C2—C1—H2107.8C8—C7—H14107.6
H1—C1—H2109.5H13—C7—H14109.5
C1—C2—H3108.2C7—C8—H15107.5
C3—C2—H3108.0C9—C8—H15107.4
C1—C2—H4109.7C7—C8—H16109.0
C3—C2—H4109.3C9—C8—H16108.7
H3—C2—H4109.5H15—C8—H16109.5
C2—C3—H5109.4C8—C9—H17108.8
C4—C3—H5109.4C10—C9—H17109.0
C2—C3—H6108.0C8—C9—H18107.6
C4—C3—H6107.8C10—C9—H18107.4
H5—C3—H6109.5H17—C9—H18109.5
C3—C4—H7107.7C9—C10—H19107.7
C5—C4—H7107.6C10i—C10—H19107.4
C3—C4—H8109.3C9—C10—H20109.4
C5—C4—H8109.2C10i—C10—H20108.4
H7—C4—H8109.5H19—C10—H20109.5
C4—C5—H9109.3
Br1—C1—C2—C3179.6 (2)C5—C6—C7—C8179.2 (3)
C1—C2—C3—C4179.4 (3)C6—C7—C8—C9179.8 (3)
C2—C3—C4—C5179.7 (3)C7—C8—C9—C10179.8 (3)
C3—C4—C5—C6179.7 (3)C8—C9—C10—C10i179.7 (3)
C4—C5—C6—C7178.8 (3)C9—C10—C10i—C9i180.0 (3)
Symmetry codes: (i) x+1, y, z+2; (ii) x+9/2, y1/2, z+3/2; (iii) x+9/2, y+1/2, z+3/2.
 

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