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The title compound, C28H18Cl6, was obtained by the electrolysis of 2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethane (DDT) in the presence of a catalytic amount of a cobalamin derivative. The molecule has a centre of symmetry, and the alkene moiety has an E configuration.
Supporting information
CCDC reference: 251635
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.099
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.07
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
(
E)-2,3-Dichloro-1,1,4,4-tetrakis(4-chlorophenyl)but-2-ene
top
Crystal data top
C28H18Cl6 | Z = 1 |
Mr = 567.12 | F(000) = 288 |
Triclinic, P1 | Dx = 1.538 Mg m−3 |
Hall symbol: -P 1 | Melting point: 234 K |
a = 7.6756 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2556 (7) Å | Cell parameters from 2309 reflections |
c = 10.2911 (8) Å | θ = 2.2–30.4° |
α = 66.459 (1)° | µ = 0.72 mm−1 |
β = 88.165 (2)° | T = 100 K |
γ = 67.361 (2)° | Plate, colourless |
V = 612.18 (8) Å3 | 0.18 × 0.15 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2494 independent reflections |
Radiation source: fine-focus sealed tube | 2229 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 8.366 pixels mm-1 | θmax = 26.4°, θmin = 2.6° |
φ and ω scans | h = −9→9 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.882, Tmax = 0.938 | l = −12→12 |
4002 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.3132P] where P = (Fo2 + 2Fc2)/3 |
2494 reflections | (Δ/σ)max = 0.003 |
154 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
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) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1009 (3) | 0.8425 (3) | 0.8106 (2) | 0.0182 (4) | |
C2 | 0.2306 (3) | 0.6826 (3) | 0.8223 (2) | 0.0229 (4) | |
H2 | 0.2961 | 0.6742 | 0.7440 | 0.028* | |
C3 | 0.2658 (3) | 0.5350 (3) | 0.9471 (2) | 0.0239 (4) | |
H3 | 0.3547 | 0.4259 | 0.9545 | 0.029* | |
C4 | 0.1702 (3) | 0.5483 (3) | 1.0604 (2) | 0.0213 (4) | |
C5 | 0.0372 (3) | 0.7044 (3) | 1.0509 (2) | 0.0230 (4) | |
H5 | −0.0302 | 0.7115 | 1.1287 | 0.028* | |
C6 | 0.0034 (3) | 0.8515 (3) | 0.9254 (2) | 0.0205 (4) | |
H6 | −0.0877 | 0.9599 | 0.9179 | 0.025* | |
C7 | 0.1985 (3) | 1.0936 (3) | 0.6937 (2) | 0.0183 (4) | |
C8 | 0.3500 (3) | 1.0113 (3) | 0.8038 (2) | 0.0232 (4) | |
H8 | 0.3745 | 0.8985 | 0.8740 | 0.028* | |
C9 | 0.4662 (3) | 1.0918 (3) | 0.8124 (2) | 0.0252 (5) | |
H9 | 0.5697 | 1.0344 | 0.8879 | 0.030* | |
C10 | 0.4304 (3) | 1.2546 (3) | 0.7111 (2) | 0.0227 (4) | |
C11 | 0.2814 (3) | 1.3403 (3) | 0.5998 (2) | 0.0258 (5) | |
H11 | 0.2582 | 1.4530 | 0.5299 | 0.031* | |
C12 | 0.1666 (3) | 1.2586 (3) | 0.5922 (2) | 0.0243 (4) | |
H12 | 0.0639 | 1.3164 | 0.5160 | 0.029* | |
C13 | 0.0670 (3) | 1.0102 (3) | 0.6800 (2) | 0.0183 (4) | |
H13 | −0.0659 | 1.0926 | 0.6755 | 0.022* | |
C14 | 0.0734 (3) | 0.9891 (2) | 0.5409 (2) | 0.0176 (4) | |
Cl1 | 0.22168 (8) | 0.36374 (7) | 1.21920 (5) | 0.02969 (16) | |
Cl2 | 0.57944 (8) | 1.35344 (7) | 0.72175 (6) | 0.03070 (16) | |
Cl3 | 0.29751 (7) | 0.93090 (7) | 0.48520 (5) | 0.02282 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0180 (9) | 0.0248 (10) | 0.0163 (9) | −0.0122 (8) | 0.0009 (7) | −0.0094 (8) |
C2 | 0.0243 (10) | 0.0280 (11) | 0.0210 (10) | −0.0132 (9) | 0.0079 (8) | −0.0124 (9) |
C3 | 0.0227 (10) | 0.0225 (10) | 0.0255 (11) | −0.0080 (8) | 0.0019 (8) | −0.0102 (9) |
C4 | 0.0233 (10) | 0.0247 (10) | 0.0162 (9) | −0.0138 (8) | −0.0016 (8) | −0.0045 (8) |
C5 | 0.0269 (11) | 0.0318 (11) | 0.0180 (10) | −0.0175 (9) | 0.0074 (8) | −0.0127 (9) |
C6 | 0.0198 (10) | 0.0255 (10) | 0.0201 (10) | −0.0107 (8) | 0.0032 (8) | −0.0120 (8) |
C7 | 0.0192 (9) | 0.0221 (10) | 0.0159 (9) | −0.0083 (8) | 0.0040 (7) | −0.0104 (8) |
C8 | 0.0234 (10) | 0.0235 (10) | 0.0200 (10) | −0.0102 (8) | 0.0001 (8) | −0.0058 (8) |
C9 | 0.0240 (11) | 0.0324 (12) | 0.0198 (10) | −0.0139 (9) | 0.0008 (8) | −0.0091 (9) |
C10 | 0.0210 (10) | 0.0292 (11) | 0.0277 (11) | −0.0138 (9) | 0.0098 (8) | −0.0184 (9) |
C11 | 0.0250 (11) | 0.0224 (10) | 0.0277 (11) | −0.0105 (9) | 0.0057 (9) | −0.0076 (9) |
C12 | 0.0232 (10) | 0.0244 (11) | 0.0204 (10) | −0.0084 (9) | −0.0008 (8) | −0.0056 (8) |
C13 | 0.0169 (9) | 0.0218 (10) | 0.0161 (9) | −0.0074 (8) | 0.0025 (7) | −0.0085 (8) |
C14 | 0.0164 (9) | 0.0195 (9) | 0.0165 (9) | −0.0068 (7) | 0.0039 (7) | −0.0077 (8) |
Cl1 | 0.0360 (3) | 0.0285 (3) | 0.0207 (3) | −0.0171 (2) | 0.0009 (2) | −0.0027 (2) |
Cl2 | 0.0300 (3) | 0.0359 (3) | 0.0416 (3) | −0.0212 (2) | 0.0123 (2) | −0.0240 (3) |
Cl3 | 0.0157 (2) | 0.0352 (3) | 0.0215 (3) | −0.0102 (2) | 0.00490 (18) | −0.0160 (2) |
Geometric parameters (Å, º) top
C1—C2 | 1.388 (3) | C7—C13 | 1.527 (3) |
C1—C6 | 1.391 (3) | C8—C9 | 1.388 (3) |
C1—C13 | 1.526 (3) | C8—H8 | 0.9500 |
C2—C3 | 1.388 (3) | C9—C10 | 1.371 (3) |
C2—H2 | 0.9500 | C9—H9 | 0.9500 |
C3—C4 | 1.379 (3) | C10—C11 | 1.381 (3) |
C3—H3 | 0.9500 | C10—Cl2 | 1.747 (2) |
C4—C5 | 1.377 (3) | C11—C12 | 1.386 (3) |
C4—Cl1 | 1.743 (2) | C11—H11 | 0.9500 |
C5—C6 | 1.391 (3) | C12—H12 | 0.9500 |
C5—H5 | 0.9500 | C13—C14 | 1.517 (3) |
C6—H6 | 0.9500 | C13—H13 | 1.0000 |
C7—C8 | 1.389 (3) | C14—C14i | 1.330 (4) |
C7—C12 | 1.392 (3) | C14—Cl3 | 1.7454 (19) |
| | | |
C2—C1—C6 | 118.71 (18) | C7—C8—H8 | 119.6 |
C2—C1—C13 | 122.83 (17) | C10—C9—C8 | 119.49 (19) |
C6—C1—C13 | 118.40 (18) | C10—C9—H9 | 120.3 |
C3—C2—C1 | 120.74 (19) | C8—C9—H9 | 120.3 |
C3—C2—H2 | 119.6 | C9—C10—C11 | 121.34 (19) |
C1—C2—H2 | 119.6 | C9—C10—Cl2 | 119.05 (16) |
C4—C3—C2 | 119.27 (19) | C11—C10—Cl2 | 119.60 (16) |
C4—C3—H3 | 120.4 | C10—C11—C12 | 118.67 (19) |
C2—C3—H3 | 120.4 | C10—C11—H11 | 120.7 |
C5—C4—C3 | 121.37 (19) | C12—C11—H11 | 120.7 |
C5—C4—Cl1 | 119.59 (16) | C11—C12—C7 | 121.43 (19) |
C3—C4—Cl1 | 119.04 (17) | C11—C12—H12 | 119.3 |
C4—C5—C6 | 118.83 (19) | C7—C12—H12 | 119.3 |
C4—C5—H5 | 120.6 | C14—C13—C1 | 112.49 (16) |
C6—C5—H5 | 120.6 | C14—C13—C7 | 111.87 (15) |
C5—C6—C1 | 121.04 (19) | C1—C13—C7 | 112.69 (15) |
C5—C6—H6 | 119.5 | C14—C13—H13 | 106.4 |
C1—C6—H6 | 119.5 | C1—C13—H13 | 106.4 |
C8—C7—C12 | 118.26 (18) | C7—C13—H13 | 106.4 |
C8—C7—C13 | 122.66 (17) | C14i—C14—C13 | 126.4 (2) |
C12—C7—C13 | 119.09 (17) | C14i—C14—Cl3 | 118.0 (2) |
C9—C8—C7 | 120.81 (19) | C13—C14—Cl3 | 115.60 (14) |
C9—C8—H8 | 119.6 | | |
Symmetry code: (i) −x, −y+2, −z+1. |
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