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In the title compound, C16H32Cl2, the mol­ecule is centrosymmetric and the molecular skeleton including both terminal Cl atoms has an all-trans conformation. The mol­ecules form layers with a thickness of c/2. These features are similar to the tilt smectic C phase of liquid crystals.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029027/ob6334sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029027/ob6334Isup2.hkl
Contains datablock I

CCDC reference: 232175

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.050
  • wR factor = 0.120
  • Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Author Response: The measured fraction (\q~max~=70.2\%) of 0.952 is relatively low, which is due to the blind region of the \c-90 setting.

Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 44 Perc. PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 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 4 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 Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 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
C16H32Cl2F(000) = 324.00
Mr = 295.32Dx = 1.107 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 20 reflections
a = 5.458 (2) Åθ = 9.4–19.7°
b = 5.3326 (19) ŵ = 3.15 mm1
c = 30.4527 (12) ÅT = 296 K
β = 91.102 (13)°Plate, colorless
V = 886.2 (5) Å30.68 × 0.26 × 0.01 mm
Z = 2
Data collection top
Rigaku AFC-5R
diffractometer
Rint = 0.035
ω scansθmax = 70.2°
Absorption correction: integration
(Coppens et al., 1965)
h = 16
Tmin = 0.622, Tmax = 0.975k = 06
2419 measured reflectionsl = 3737
1613 independent reflections3 standard reflections every 150 reflections
715 reflections with F2 > 2σ(F2) intensity decay: 6.2%
Refinement top
Refinement on F2 w = 4Fo2/[0.0001Fo2 + σ2(Fo) + 0.1]
R[F2 > 2σ(F2)] = 0.050(Δ/σ)max < 0.001
wR(F2) = 0.120Δρmax = 0.62 e Å3
S = 1.00Δρmin = 0.72 e Å3
1613 reflectionsExtinction correction: Larson (1970)
99 parametersExtinction coefficient: 35.6 (2)
H-atom parameters constrained
Special details top

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
Cl10.8481 (2)0.0756 (2)0.28256 (3)0.0874 (4)
C10.6768 (7)0.3484 (7)0.2957 (1)0.077 (1)
C20.5065 (6)0.3115 (8)0.3341 (1)0.068 (1)
C30.3666 (6)0.5460 (7)0.3469 (1)0.066 (1)
C40.1973 (6)0.5090 (7)0.3862 (1)0.066 (1)
C50.0562 (6)0.7386 (7)0.3999 (1)0.063 (1)
C60.1137 (6)0.6988 (7)0.4399 (1)0.063 (1)
C70.2590 (6)0.9271 (7)0.4535 (1)0.063 (1)
C80.4273 (6)0.8854 (6)0.4930 (1)0.063 (1)
H10.58000.38970.27110.092*
H20.78530.48300.30160.092*
H30.39230.18280.32760.081*
H40.60220.26230.35830.081*
H50.27060.59560.32270.079*
H60.48040.67490.35340.079*
H70.08350.38060.37940.079*
H80.29410.45720.41020.078*
H90.16970.86700.40680.076*
H100.04050.79080.37600.076*
H110.22470.56780.43300.076*
H120.01630.64940.46390.076*
H130.35730.97630.42950.075*
H140.14841.05850.46020.075*
H150.32970.83630.51710.076*
H160.53880.75460.48640.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0925 (8)0.0823 (8)0.0864 (7)0.0176 (7)0.0245 (5)0.0040 (7)
C10.080 (3)0.072 (3)0.077 (3)0.012 (2)0.019 (2)0.001 (2)
C20.069 (3)0.064 (3)0.069 (3)0.001 (2)0.017 (2)0.001 (2)
C30.068 (3)0.067 (3)0.061 (2)0.003 (2)0.014 (2)0.001 (2)
C40.070 (2)0.063 (3)0.064 (2)0.005 (2)0.015 (2)0.002 (2)
C50.068 (3)0.062 (3)0.060 (2)0.001 (2)0.009 (2)0.002 (2)
C60.070 (3)0.060 (2)0.060 (2)0.004 (2)0.011 (2)0.003 (2)
C70.071 (2)0.060 (2)0.057 (2)0.004 (2)0.012 (2)0.001 (2)
C80.071 (3)0.062 (3)0.056 (2)0.004 (2)0.008 (2)0.002 (2)
Geometric parameters (Å, º) top
Cl1—C11.771 (4)C3—H50.95
C1—C21.492 (4)C3—H60.95
C2—C31.512 (5)C4—H70.95
C3—C41.511 (4)C4—H80.95
C4—C51.502 (4)C5—H90.95
C5—C61.529 (4)C5—H100.95
C6—C71.507 (4)C6—H110.95
C7—C81.517 (4)C6—H120.95
C8—C8i1.514 (5)C7—H130.95
C1—H10.95C7—H140.95
C1—H20.95C8—H150.95
C2—H30.95C8—H160.95
C2—H40.95
Cl1···Cl1ii3.697 (2)Cl1···Cl1iii3.697 (2)
Cl1—C1—C2112.8 (3)C3—C4—H7108.3
C1—C2—C3113.4 (3)C5—C4—H7108.3
C2—C3—C4113.2 (3)C3—C4—H8107.8
C3—C4—C5114.6 (3)C5—C4—H8108.2
C4—C5—C6114.1 (3)H7—C4—H8109.5
C5—C6—C7114.5 (3)C4—C5—H9108.4
C6—C7—C8114.0 (3)C6—C5—H9108.2
C7—C8—C8i114.3 (3)C4—C5—H10108.3
Cl1—C1—H1108.2C6—C5—H10108.3
C2—C1—H1107.4H9—C5—H10109.5
Cl1—C1—H2109.6C5—C6—H11107.9
C2—C1—H2109.3C7—C6—H11108.7
H1—C1—H2109.5C5—C6—H12108.1
C1—C2—H3109.6C7—C6—H12108.2
C3—C2—H3108.7H11—C6—H12109.5
C1—C2—H4107.5C6—C7—H13108.3
C3—C2—H4108.1C8—C7—H13107.9
H3—C2—H4109.5C6—C7—H14108.8
C2—C3—H5108.2C8—C7—H14108.3
C4—C3—H5108.2H13—C7—H14109.5
C2—C3—H6108.9C7—C8—H15108.2
C4—C3—H6108.7C7—C8—H16108.6
H5—C3—H6109.5H15—C8—H16109.5
Cl1—C1—C2—C3177.6 (2)C4—C5—C6—C7179.1 (3)
C1—C2—C3—C4179.1 (3)C5—C6—C7—C8179.9 (3)
C2—C3—C4—C5179.8 (3)C6—C7—C8—C8i179.7 (3)
C3—C4—C5—C6179.8 (3)C7—C8—C8i—C7i180.0
Symmetry codes: (i) x+1, y+2, z+1; (ii) x2, y1/2, z+1/2; (iii) x2, y+1/2, z+1/2.
 

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