The title compound, C19H21Cl, exhibits a symmetrically arranged 1,3-diphenyl-2,2-dimethylpropyl entity, with a 1-chloro and a 3-vinyl substituent displaced on opposite sides of the plane defined by the three C atoms that bridge the two aromatic subunits.
Supporting information
CCDC reference: 262477
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.055
- wR factor = 0.113
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT432_ALERT_2_A Short Inter X...Y Contact C1 .. C1 .. 2.71 Ang.
| Author Response: The observed close contacts are due to the two different
orientations of (I) at each crystallographic independent position.
|
Alert level B
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C2'
PLAT432_ALERT_2_B Short Inter X...Y Contact C1' .. C1' .. 2.97 Ang.
| Author Response: The observed close contacts are due to the two different
orientations of (I) at each crystallographic independent position.
|
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.43 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.27 Ratio
PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 8.30 Deg.
C2 -C3 -CL1' 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 6.30 Deg.
C2' -C5 -CL1 1.555 1.555 1.555
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 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
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Diffractometer Control Software (Enraf–Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2002 (Spek, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
1-Chloro-2,2-dimethyl-1,3-diphenylpent-4-ene
top
Crystal data top
C19H21Cl | F(000) = 608 |
Mr = 284.81 | Dx = 1.224 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8829 (9) Å | Cell parameters from 25 reflections |
b = 7.2027 (5) Å | θ = 10.0–25.0° |
c = 15.4632 (10) Å | µ = 0.24 mm−1 |
β = 92.142 (2)° | T = 100 K |
V = 1545.15 (18) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.10 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 26.4°, θmin = 1.9° |
Graphite monochromator | h = −17→17 |
ω/2θ scans | k = 0→9 |
3134 measured reflections | l = 0→19 |
3134 independent reflections | 3 standard reflections every 100 reflections |
2604 reflections with I > 2σ(I) | intensity decay: 0.3% |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.03P)2 + 1.1424P] where P = (Fo2 + 2Fc2)/3 |
3134 reflections | (Δ/σ)max = 0.001 |
211 parameters | Δρmax = 0.31 e Å−3 |
41 restraints | Δρmin = −0.21 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 | Occ. (<1) |
Cl1 | 0.3161 (2) | 0.5191 (3) | 0.47804 (19) | 0.0223 (5) | 0.450 (3) |
C1 | 0.4094 (4) | 0.9874 (8) | 0.5290 (3) | 0.0297 (12) | 0.450 (3) |
H1A | 0.4349 | 0.8706 | 0.5467 | 0.036* | 0.450 (3) |
H1B | 0.4509 | 1.0804 | 0.5077 | 0.036* | 0.450 (3) |
C2 | 0.3155 (9) | 1.021 (3) | 0.5339 (15) | 0.030 (3) | 0.450 (3) |
H2A | 0.2911 | 1.1385 | 0.5158 | 0.036* | 0.450 (3) |
Cl1' | 0.3368 (2) | 1.0162 (5) | 0.5362 (3) | 0.0241 (6) | 0.550 (3) |
C1' | 0.3976 (4) | 0.5233 (6) | 0.4713 (3) | 0.0341 (11) | 0.550 (3) |
H1C | 0.4283 | 0.6154 | 0.4380 | 0.041* | 0.550 (3) |
H1D | 0.4349 | 0.4296 | 0.4999 | 0.041* | 0.550 (3) |
C2' | 0.2990 (9) | 0.5256 (19) | 0.4780 (9) | 0.060 (4) | 0.550 (3) |
H2B | 0.2668 | 0.4349 | 0.5109 | 0.072* | 0.550 (3) |
C3 | 0.24304 (14) | 0.8706 (3) | 0.56895 (13) | 0.0201 (4) | |
H3 | 0.2819 | 0.7649 | 0.5937 | 0.024* | |
C4 | 0.17775 (14) | 0.7943 (3) | 0.49261 (12) | 0.0174 (4) | |
C5 | 0.24159 (14) | 0.6864 (3) | 0.42838 (13) | 0.0187 (4) | |
H5 | 0.2857 | 0.7807 | 0.4036 | 0.022* | |
C6 | 0.10105 (16) | 0.6694 (3) | 0.53077 (14) | 0.0260 (5) | |
H6A | 0.0605 | 0.7432 | 0.5683 | 0.039* | |
H6B | 0.1325 | 0.5701 | 0.5647 | 0.039* | |
H6C | 0.0610 | 0.6150 | 0.4838 | 0.039* | |
C7 | 0.12741 (16) | 0.9510 (3) | 0.44176 (14) | 0.0247 (5) | |
H7A | 0.0837 | 0.8979 | 0.3971 | 0.037* | |
H7B | 0.1758 | 1.0282 | 0.4144 | 0.037* | |
H7C | 0.0905 | 1.0272 | 0.4812 | 0.037* | |
C8 | 0.18547 (14) | 0.6021 (3) | 0.35176 (13) | 0.0187 (4) | |
C9 | 0.18218 (14) | 0.6941 (3) | 0.27243 (13) | 0.0202 (4) | |
H9 | 0.2157 | 0.8082 | 0.2667 | 0.024* | |
C10 | 0.13069 (15) | 0.6213 (3) | 0.20177 (14) | 0.0243 (5) | |
H10 | 0.1293 | 0.6855 | 0.1481 | 0.029* | |
C11 | 0.08131 (15) | 0.4552 (3) | 0.20913 (14) | 0.0240 (5) | |
H11 | 0.0455 | 0.4063 | 0.1608 | 0.029* | |
C12 | 0.08443 (15) | 0.3607 (3) | 0.28725 (14) | 0.0246 (5) | |
H12 | 0.0510 | 0.2464 | 0.2926 | 0.030* | |
C13 | 0.13661 (15) | 0.4335 (3) | 0.35777 (14) | 0.0218 (5) | |
H13 | 0.1391 | 0.3674 | 0.4110 | 0.026* | |
C14 | 0.18857 (14) | 0.9587 (3) | 0.64188 (13) | 0.0190 (4) | |
C15 | 0.14922 (15) | 1.1368 (3) | 0.63722 (14) | 0.0236 (5) | |
H15 | 0.1589 | 1.2112 | 0.5875 | 0.028* | |
C16 | 0.09624 (16) | 1.2068 (3) | 0.70410 (15) | 0.0280 (5) | |
H16 | 0.0685 | 1.3271 | 0.6994 | 0.034* | |
C17 | 0.08370 (15) | 1.1015 (3) | 0.77787 (15) | 0.0283 (5) | |
H17 | 0.0473 | 1.1494 | 0.8237 | 0.034* | |
C18 | 0.12418 (15) | 0.9272 (3) | 0.78454 (14) | 0.0253 (5) | |
H18 | 0.1164 | 0.8556 | 0.8354 | 0.030* | |
C19 | 0.17624 (15) | 0.8558 (3) | 0.71723 (13) | 0.0225 (5) | |
H19 | 0.2038 | 0.7354 | 0.7225 | 0.027* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0289 (13) | 0.0184 (8) | 0.0192 (10) | 0.0079 (7) | −0.0051 (7) | −0.0023 (7) |
C1 | 0.020 (3) | 0.038 (3) | 0.031 (3) | −0.007 (2) | 0.003 (2) | 0.003 (2) |
C2 | 0.030 (6) | 0.039 (5) | 0.021 (5) | 0.009 (4) | 0.008 (5) | −0.009 (4) |
Cl1' | 0.0227 (12) | 0.0238 (9) | 0.0264 (9) | −0.0083 (8) | 0.0070 (9) | −0.0045 (7) |
C1' | 0.039 (3) | 0.030 (2) | 0.034 (3) | 0.0140 (19) | 0.010 (2) | 0.0119 (19) |
C2' | 0.046 (5) | 0.077 (7) | 0.058 (7) | −0.006 (4) | 0.006 (4) | −0.032 (5) |
C3 | 0.0213 (11) | 0.0190 (10) | 0.0201 (11) | 0.0002 (8) | −0.0006 (9) | −0.0002 (8) |
C4 | 0.0206 (10) | 0.0173 (9) | 0.0145 (10) | −0.0010 (8) | 0.0010 (8) | −0.0012 (8) |
C5 | 0.0212 (11) | 0.0164 (9) | 0.0187 (11) | −0.0002 (8) | 0.0020 (8) | 0.0016 (8) |
C6 | 0.0293 (12) | 0.0255 (11) | 0.0234 (12) | −0.0094 (9) | 0.0053 (10) | −0.0053 (9) |
C7 | 0.0277 (12) | 0.0246 (11) | 0.0216 (11) | 0.0054 (9) | −0.0014 (9) | −0.0023 (9) |
C8 | 0.0193 (10) | 0.0180 (10) | 0.0191 (11) | 0.0023 (8) | 0.0030 (8) | −0.0037 (8) |
C9 | 0.0215 (11) | 0.0172 (10) | 0.0221 (11) | −0.0005 (8) | 0.0052 (9) | −0.0018 (8) |
C10 | 0.0246 (11) | 0.0302 (11) | 0.0182 (11) | 0.0067 (9) | 0.0023 (9) | 0.0004 (9) |
C11 | 0.0191 (11) | 0.0308 (11) | 0.0219 (11) | 0.0020 (9) | −0.0024 (9) | −0.0103 (9) |
C12 | 0.0244 (11) | 0.0230 (11) | 0.0269 (12) | −0.0036 (9) | 0.0062 (9) | −0.0082 (9) |
C13 | 0.0269 (11) | 0.0199 (10) | 0.0187 (11) | −0.0009 (9) | 0.0050 (9) | −0.0009 (8) |
C14 | 0.0160 (10) | 0.0222 (10) | 0.0184 (11) | −0.0022 (8) | −0.0030 (8) | −0.0047 (8) |
C15 | 0.0277 (12) | 0.0223 (10) | 0.0205 (11) | −0.0007 (9) | −0.0014 (9) | −0.0017 (9) |
C16 | 0.0279 (12) | 0.0260 (11) | 0.0298 (13) | 0.0062 (9) | −0.0040 (10) | −0.0092 (10) |
C17 | 0.0214 (12) | 0.0400 (13) | 0.0236 (12) | 0.0019 (10) | 0.0025 (9) | −0.0092 (10) |
C18 | 0.0251 (12) | 0.0332 (12) | 0.0174 (11) | −0.0040 (9) | −0.0010 (9) | −0.0020 (9) |
C19 | 0.0226 (11) | 0.0231 (10) | 0.0214 (11) | 0.0008 (8) | −0.0050 (9) | −0.0024 (9) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.747 (3) | C7—H7B | 0.9800 |
C1—C2 | 1.331 (13) | C7—H7C | 0.9800 |
C1—H1A | 0.9500 | C8—C9 | 1.393 (3) |
C1—H1B | 0.9500 | C8—C13 | 1.396 (3) |
C2—C3 | 1.587 (15) | C9—C10 | 1.386 (3) |
C2—H2A | 0.9500 | C9—H9 | 0.9500 |
Cl1'—C3 | 1.760 (3) | C10—C11 | 1.386 (3) |
C1'—C2' | 1.376 (12) | C10—H10 | 0.9500 |
C1'—H1C | 0.9500 | C11—C12 | 1.386 (3) |
C1'—H1D | 0.9500 | C11—H11 | 0.9500 |
C2'—C5 | 1.588 (12) | C12—C13 | 1.389 (3) |
C2'—H2B | 0.9500 | C12—H12 | 0.9500 |
C3—C14 | 1.520 (3) | C13—H13 | 0.9500 |
C3—C4 | 1.561 (3) | C14—C15 | 1.395 (3) |
C3—H3 | 1.0000 | C14—C19 | 1.397 (3) |
C4—C6 | 1.529 (3) | C15—C16 | 1.386 (3) |
C4—C7 | 1.530 (3) | C15—H15 | 0.9500 |
C4—C5 | 1.562 (3) | C16—C17 | 1.386 (3) |
C5—C8 | 1.520 (3) | C16—H16 | 0.9500 |
C5—H5 | 1.0000 | C17—C18 | 1.378 (3) |
C6—H6A | 0.9800 | C17—H17 | 0.9500 |
C6—H6B | 0.9800 | C18—C19 | 1.388 (3) |
C6—H6C | 0.9800 | C18—H18 | 0.9500 |
C7—H7A | 0.9800 | C19—H19 | 0.9500 |
| | | |
C2—C1—H1A | 120.0 | H6B—C6—H6C | 109.5 |
C2—C1—H1B | 120.0 | C4—C7—H7A | 109.5 |
H1A—C1—H1B | 120.0 | C4—C7—H7B | 109.5 |
C1—C2—C3 | 122.0 (14) | H7A—C7—H7B | 109.5 |
C1—C2—H2A | 119.0 | C4—C7—H7C | 109.5 |
C3—C2—H2A | 119.0 | H7A—C7—H7C | 109.5 |
C2'—C1'—H1C | 120.0 | H7B—C7—H7C | 109.5 |
C2'—C1'—H1D | 120.0 | C9—C8—C13 | 118.20 (19) |
H1C—C1'—H1D | 120.0 | C9—C8—C5 | 119.67 (18) |
C1'—C2'—C5 | 117.1 (10) | C13—C8—C5 | 122.14 (18) |
C1'—C2'—H2B | 121.5 | C10—C9—C8 | 120.85 (19) |
C5—C2'—H2B | 121.5 | C10—C9—H9 | 119.6 |
C14—C3—C4 | 114.66 (16) | C8—C9—H9 | 119.6 |
C14—C3—C2 | 107.9 (8) | C11—C10—C9 | 120.3 (2) |
C4—C3—C2 | 109.8 (9) | C11—C10—H10 | 119.9 |
C14—C3—Cl1' | 111.0 (2) | C9—C10—H10 | 119.9 |
C4—C3—Cl1' | 114.0 (2) | C10—C11—C12 | 119.7 (2) |
C2—C3—Cl1' | 8.3 (7) | C10—C11—H11 | 120.1 |
C14—C3—H3 | 108.1 | C12—C11—H11 | 120.1 |
C4—C3—H3 | 108.1 | C11—C12—C13 | 119.8 (2) |
C2—C3—H3 | 108.1 | C11—C12—H12 | 120.1 |
Cl1'—C3—H3 | 99.8 | C13—C12—H12 | 120.1 |
C6—C4—C7 | 108.72 (17) | C12—C13—C8 | 121.1 (2) |
C6—C4—C3 | 107.96 (16) | C12—C13—H13 | 119.5 |
C7—C4—C3 | 111.73 (16) | C8—C13—H13 | 119.5 |
C6—C4—C5 | 111.87 (16) | C15—C14—C19 | 118.11 (19) |
C7—C4—C5 | 107.41 (16) | C15—C14—C3 | 123.39 (19) |
C3—C4—C5 | 109.18 (16) | C19—C14—C3 | 118.50 (18) |
C8—C5—C4 | 114.06 (16) | C16—C15—C14 | 120.9 (2) |
C8—C5—C2' | 108.6 (5) | C16—C15—H15 | 119.6 |
C4—C5—C2' | 110.0 (5) | C14—C15—H15 | 119.6 |
C8—C5—Cl1 | 110.16 (17) | C15—C16—C17 | 120.1 (2) |
C4—C5—Cl1 | 113.85 (17) | C15—C16—H16 | 120.0 |
C2'—C5—Cl1 | 6.3 (6) | C17—C16—H16 | 120.0 |
C8—C5—H5 | 106.0 | C18—C17—C16 | 119.8 (2) |
C4—C5—H5 | 106.0 | C18—C17—H17 | 120.1 |
C2'—C5—H5 | 112.2 | C16—C17—H17 | 120.1 |
Cl1—C5—H5 | 106.0 | C17—C18—C19 | 120.3 (2) |
C4—C6—H6A | 109.5 | C17—C18—H18 | 119.9 |
C4—C6—H6B | 109.5 | C19—C18—H18 | 119.9 |
H6A—C6—H6B | 109.5 | C18—C19—C14 | 120.8 (2) |
C4—C6—H6C | 109.5 | C18—C19—H19 | 119.6 |
H6A—C6—H6C | 109.5 | C14—C19—H19 | 119.6 |
| | | |
C1—C2—C3—C14 | 125.7 (17) | Cl1—C5—C8—C9 | −131.8 (2) |
C1—C2—C3—C4 | −108.7 (18) | C4—C5—C8—C13 | −81.4 (2) |
C1—C2—C3—Cl1' | 13 (5) | C2'—C5—C8—C13 | 41.6 (6) |
C14—C3—C4—C6 | −51.2 (2) | Cl1—C5—C8—C13 | 48.0 (2) |
C2—C3—C4—C6 | −172.9 (7) | C13—C8—C9—C10 | 0.9 (3) |
Cl1'—C3—C4—C6 | 179.35 (18) | C5—C8—C9—C10 | −179.31 (18) |
C14—C3—C4—C7 | 68.3 (2) | C8—C9—C10—C11 | 0.1 (3) |
C2—C3—C4—C7 | −53.4 (7) | C9—C10—C11—C12 | −0.7 (3) |
Cl1'—C3—C4—C7 | −61.2 (2) | C10—C11—C12—C13 | 0.3 (3) |
C14—C3—C4—C5 | −172.99 (16) | C11—C12—C13—C8 | 0.7 (3) |
C2—C3—C4—C5 | 65.3 (7) | C9—C8—C13—C12 | −1.3 (3) |
Cl1'—C3—C4—C5 | 57.5 (2) | C5—C8—C13—C12 | 178.89 (19) |
C6—C4—C5—C8 | 59.5 (2) | C4—C3—C14—C15 | −77.8 (2) |
C7—C4—C5—C8 | −59.8 (2) | C2—C3—C14—C15 | 44.9 (8) |
C3—C4—C5—C8 | 178.92 (16) | Cl1'—C3—C14—C15 | 53.1 (3) |
C6—C4—C5—C2' | −62.8 (6) | C4—C3—C14—C19 | 101.5 (2) |
C7—C4—C5—C2' | 178.0 (6) | C2—C3—C14—C19 | −135.8 (8) |
C3—C4—C5—C2' | 56.7 (6) | Cl1'—C3—C14—C19 | −127.6 (2) |
C6—C4—C5—Cl1 | −68.1 (2) | C19—C14—C15—C16 | −2.4 (3) |
C7—C4—C5—Cl1 | 172.65 (17) | C3—C14—C15—C16 | 176.87 (19) |
C3—C4—C5—Cl1 | 51.3 (2) | C14—C15—C16—C17 | 1.6 (3) |
C1'—C2'—C5—C8 | 108.9 (9) | C15—C16—C17—C18 | 0.1 (3) |
C1'—C2'—C5—C4 | −125.6 (9) | C16—C17—C18—C19 | −0.9 (3) |
C1'—C2'—C5—Cl1 | 3 (5) | C17—C18—C19—C14 | 0.0 (3) |
C4—C5—C8—C9 | 98.7 (2) | C15—C14—C19—C18 | 1.6 (3) |
C2'—C5—C8—C9 | −138.2 (6) | C3—C14—C19—C18 | −177.72 (18) |