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
CCDC reference: 232175
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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.
Crystal data top
C16H32Cl2 | F(000) = 324.00 |
Mr = 295.32 | Dx = 1.107 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 20 reflections |
a = 5.458 (2) Å | θ = 9.4–19.7° |
b = 5.3326 (19) Å | µ = 3.15 mm−1 |
c = 30.4527 (12) Å | T = 296 K |
β = 91.102 (13)° | Plate, colorless |
V = 886.2 (5) Å3 | 0.68 × 0.26 × 0.01 mm |
Z = 2 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.035 |
ω scans | θmax = 70.2° |
Absorption correction: integration (Coppens et al., 1965) | h = −1→6 |
Tmin = 0.622, Tmax = 0.975 | k = 0→6 |
2419 measured reflections | l = −37→37 |
1613 independent reflections | 3 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) = 0.120 | Δρmax = 0.62 e Å−3 |
S = 1.00 | Δρmin = −0.72 e Å−3 |
1613 reflections | Extinction correction: Larson (1970) |
99 parameters | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl1 | −0.8481 (2) | 0.0756 (2) | 0.28256 (3) | 0.0874 (4) | |
C1 | −0.6768 (7) | 0.3484 (7) | 0.2957 (1) | 0.077 (1) | |
C2 | −0.5065 (6) | 0.3115 (8) | 0.3341 (1) | 0.068 (1) | |
C3 | −0.3666 (6) | 0.5460 (7) | 0.3469 (1) | 0.066 (1) | |
C4 | −0.1973 (6) | 0.5090 (7) | 0.3862 (1) | 0.066 (1) | |
C5 | −0.0562 (6) | 0.7386 (7) | 0.3999 (1) | 0.063 (1) | |
C6 | 0.1137 (6) | 0.6988 (7) | 0.4399 (1) | 0.063 (1) | |
C7 | 0.2590 (6) | 0.9271 (7) | 0.4535 (1) | 0.063 (1) | |
C8 | 0.4273 (6) | 0.8854 (6) | 0.4930 (1) | 0.063 (1) | |
H1 | −0.5800 | 0.3897 | 0.2711 | 0.092* | |
H2 | −0.7853 | 0.4830 | 0.3016 | 0.092* | |
H3 | −0.3923 | 0.1828 | 0.3276 | 0.081* | |
H4 | −0.6022 | 0.2623 | 0.3583 | 0.081* | |
H5 | −0.2706 | 0.5956 | 0.3227 | 0.079* | |
H6 | −0.4804 | 0.6749 | 0.3534 | 0.079* | |
H7 | −0.0835 | 0.3806 | 0.3794 | 0.079* | |
H8 | −0.2941 | 0.4572 | 0.4102 | 0.078* | |
H9 | −0.1697 | 0.8670 | 0.4068 | 0.076* | |
H10 | 0.0405 | 0.7908 | 0.3760 | 0.076* | |
H11 | 0.2247 | 0.5678 | 0.4330 | 0.076* | |
H12 | 0.0163 | 0.6494 | 0.4639 | 0.076* | |
H13 | 0.3573 | 0.9763 | 0.4295 | 0.075* | |
H14 | 0.1484 | 1.0585 | 0.4602 | 0.075* | |
H15 | 0.3297 | 0.8363 | 0.5171 | 0.076* | |
H16 | 0.5388 | 0.7546 | 0.4864 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0925 (8) | 0.0823 (8) | 0.0864 (7) | −0.0176 (7) | −0.0245 (5) | −0.0040 (7) |
C1 | 0.080 (3) | 0.072 (3) | 0.077 (3) | −0.012 (2) | −0.019 (2) | 0.001 (2) |
C2 | 0.069 (3) | 0.064 (3) | 0.069 (3) | 0.001 (2) | −0.017 (2) | 0.001 (2) |
C3 | 0.068 (3) | 0.067 (3) | 0.061 (2) | −0.003 (2) | −0.014 (2) | −0.001 (2) |
C4 | 0.070 (2) | 0.063 (3) | 0.064 (2) | −0.005 (2) | −0.015 (2) | 0.002 (2) |
C5 | 0.068 (3) | 0.062 (3) | 0.060 (2) | −0.001 (2) | −0.009 (2) | 0.002 (2) |
C6 | 0.070 (3) | 0.060 (2) | 0.060 (2) | −0.004 (2) | −0.011 (2) | 0.003 (2) |
C7 | 0.071 (2) | 0.060 (2) | 0.057 (2) | −0.004 (2) | −0.012 (2) | −0.001 (2) |
C8 | 0.071 (3) | 0.062 (3) | 0.056 (2) | −0.004 (2) | −0.008 (2) | 0.002 (2) |
Geometric parameters (Å, º) top
Cl1—C1 | 1.771 (4) | C3—H5 | 0.95 |
C1—C2 | 1.492 (4) | C3—H6 | 0.95 |
C2—C3 | 1.512 (5) | C4—H7 | 0.95 |
C3—C4 | 1.511 (4) | C4—H8 | 0.95 |
C4—C5 | 1.502 (4) | C5—H9 | 0.95 |
C5—C6 | 1.529 (4) | C5—H10 | 0.95 |
C6—C7 | 1.507 (4) | C6—H11 | 0.95 |
C7—C8 | 1.517 (4) | C6—H12 | 0.95 |
C8—C8i | 1.514 (5) | C7—H13 | 0.95 |
C1—H1 | 0.95 | C7—H14 | 0.95 |
C1—H2 | 0.95 | C8—H15 | 0.95 |
C2—H3 | 0.95 | C8—H16 | 0.95 |
C2—H4 | 0.95 | | |
| | | |
Cl1···Cl1ii | 3.697 (2) | Cl1···Cl1iii | 3.697 (2) |
| | | |
Cl1—C1—C2 | 112.8 (3) | C3—C4—H7 | 108.3 |
C1—C2—C3 | 113.4 (3) | C5—C4—H7 | 108.3 |
C2—C3—C4 | 113.2 (3) | C3—C4—H8 | 107.8 |
C3—C4—C5 | 114.6 (3) | C5—C4—H8 | 108.2 |
C4—C5—C6 | 114.1 (3) | H7—C4—H8 | 109.5 |
C5—C6—C7 | 114.5 (3) | C4—C5—H9 | 108.4 |
C6—C7—C8 | 114.0 (3) | C6—C5—H9 | 108.2 |
C7—C8—C8i | 114.3 (3) | C4—C5—H10 | 108.3 |
Cl1—C1—H1 | 108.2 | C6—C5—H10 | 108.3 |
C2—C1—H1 | 107.4 | H9—C5—H10 | 109.5 |
Cl1—C1—H2 | 109.6 | C5—C6—H11 | 107.9 |
C2—C1—H2 | 109.3 | C7—C6—H11 | 108.7 |
H1—C1—H2 | 109.5 | C5—C6—H12 | 108.1 |
C1—C2—H3 | 109.6 | C7—C6—H12 | 108.2 |
C3—C2—H3 | 108.7 | H11—C6—H12 | 109.5 |
C1—C2—H4 | 107.5 | C6—C7—H13 | 108.3 |
C3—C2—H4 | 108.1 | C8—C7—H13 | 107.9 |
H3—C2—H4 | 109.5 | C6—C7—H14 | 108.8 |
C2—C3—H5 | 108.2 | C8—C7—H14 | 108.3 |
C4—C3—H5 | 108.2 | H13—C7—H14 | 109.5 |
C2—C3—H6 | 108.9 | C7—C8—H15 | 108.2 |
C4—C3—H6 | 108.7 | C7—C8—H16 | 108.6 |
H5—C3—H6 | 109.5 | H15—C8—H16 | 109.5 |
| | | |
Cl1—C1—C2—C3 | −177.6 (2) | C4—C5—C6—C7 | 179.1 (3) |
C1—C2—C3—C4 | 179.1 (3) | C5—C6—C7—C8 | −179.9 (3) |
C2—C3—C4—C5 | −179.8 (3) | C6—C7—C8—C8i | −179.7 (3) |
C3—C4—C5—C6 | 179.8 (3) | C7—C8—C8i—C7i | 180.0 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x−2, y−1/2, −z+1/2; (iii) −x−2, y+1/2, −z+1/2. |