Literature DB >> 21522713

2'-Iodo-2,2'',3,3'',4,4'',5,5'',6,6''-deca-methyl-1,1':3',1''-terphenyl chloro-form monosolvate.

Marian Olaru1, Sorin Roşca, Ciprian I Raţ.   

Abstract

The title compound, C(28)H(33)I·CHCl(3), forms dimers through C-I⋯π inter-actions. The crystal structure is consolidated by the presence of C-H⋯π inter-actions between the chloro-form solvent and the main mol-ecule.

Entities:  

Year:  2010        PMID: 21522713      PMCID: PMC3050376          DOI: 10.1107/S1600536810052736

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the synthesis and spectroscopic characterization of 2′-iodo-2,2′′,3,3′′,4,4′′,5,5′′,6,6′′-deca­methyl-1,1′:3′,1′′-terphenyl, see: Hino et al. (2005 ▶); Duttwyler et al. (2008 ▶). For related m-terphenyl iodides, see: Niemeyer (1998 ▶); Twamley et al. (2000 ▶); Zakharov et al. (2003 ▶). For general background to compounds with m-terphenyl substituents, see: Power (2004 ▶).

Experimental

Crystal data

C28H33I·CHCl3 M = 615.81 Monoclinic, a = 12.0294 (10) Å b = 16.0651 (13) Å c = 15.3762 (12) Å β = 103.385 (1)° V = 2890.8 (4) Å3 Z = 4 Mo Kα radiation μ = 1.40 mm−1 T = 297 K 0.32 × 0.28 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.663, T max = 0.712 22910 measured reflections 5896 independent reflections 4698 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.066 wR(F 2) = 0.137 S = 1.13 5896 reflections 308 parameters H-atom parameters constrained Δρmax = 0.83 e Å−3 Δρmin = −0.68 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052736/pk2291sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052736/pk2291Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C28H33I·CHCl3F(000) = 1248
Mr = 615.81Dx = 1.415 Mg m3
Monoclinic, P21/nMelting point = 498–497 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.0294 (10) ÅCell parameters from 3032 reflections
b = 16.0651 (13) Åθ = 2.3–19.9°
c = 15.3762 (12) ŵ = 1.40 mm1
β = 103.385 (1)°T = 297 K
V = 2890.8 (4) Å3Block, colourless
Z = 40.32 × 0.28 × 0.26 mm
Bruker SMART CCD area-detector diffractometer5896 independent reflections
Radiation source: fine-focus sealed tube4698 reflections with I > 2σ(I)
graphiteRint = 0.056
φ and ω scansθmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −15→15
Tmin = 0.663, Tmax = 0.712k = −20→20
22910 measured reflectionsl = −19→19
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.13w = 1/[σ2(Fo2) + (0.0465P)2 + 3.6212P] where P = (Fo2 + 2Fc2)/3
5896 reflections(Δ/σ)max = 0.031
308 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = −0.68 e Å3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
C10.7505 (4)0.1344 (3)0.4780 (3)0.0364 (11)
C20.6846 (4)0.1920 (3)0.4197 (3)0.0383 (11)
C30.6011 (5)0.2346 (3)0.4498 (3)0.0499 (13)
H30.55560.2730.41220.06*
C40.5835 (5)0.2216 (4)0.5341 (4)0.0570 (15)
H40.52780.25180.55350.068*
C50.6487 (5)0.1637 (3)0.5897 (3)0.0490 (13)
H50.63540.15440.64610.059*
C60.7338 (4)0.1191 (3)0.5631 (3)0.0377 (11)
C70.6986 (4)0.2074 (3)0.3265 (3)0.0377 (11)
C80.6370 (4)0.1577 (3)0.2572 (3)0.0422 (12)
C90.6476 (4)0.1740 (3)0.1698 (3)0.0476 (13)
C100.7155 (5)0.2388 (3)0.1525 (3)0.0493 (13)
C110.7780 (4)0.2865 (3)0.2222 (3)0.0473 (12)
C120.7713 (4)0.2701 (3)0.3103 (3)0.0422 (12)
C130.5589 (6)0.0903 (4)0.2764 (4)0.0680 (17)
H13A0.48230.10090.24310.102*
H13B0.56070.08980.33910.102*
H13C0.58390.03740.25920.102*
C140.5810 (7)0.1203 (5)0.0945 (4)0.084 (2)
H14A0.61450.12440.04380.125*
H14B0.50310.1390.07820.125*
H14C0.58310.06340.11390.125*
C150.7196 (6)0.2594 (5)0.0568 (4)0.084 (2)
H15A0.65840.23140.01630.127*
H15B0.79140.24150.0460.127*
H15C0.71170.31840.04760.127*
C160.8538 (6)0.3562 (4)0.2035 (5)0.079 (2)
H16A0.8130.38860.15380.118*
H16B0.92110.33310.18950.118*
H16C0.87530.39110.25530.118*
C170.8413 (5)0.3199 (4)0.3880 (4)0.0681 (17)
H17A0.82680.29970.4430.102*
H17B0.82040.37760.38070.102*
H17C0.92110.31390.38930.102*
C180.8017 (4)0.0550 (3)0.6229 (3)0.0368 (11)
C190.7593 (4)−0.0266 (3)0.6220 (3)0.0396 (11)
C200.8242 (5)−0.0875 (3)0.6762 (3)0.0468 (13)
C210.9318 (5)−0.0657 (3)0.7299 (3)0.0489 (13)
C220.9726 (4)0.0152 (3)0.7312 (3)0.0459 (12)
C230.9068 (4)0.0763 (3)0.6789 (3)0.0447 (12)
C240.6463 (5)−0.0464 (4)0.5600 (4)0.0608 (16)
H24A0.6358−0.10560.55650.091*
H24B0.645−0.02480.50150.091*
H24C0.5859−0.02140.58220.091*
C250.7790 (6)−0.1748 (3)0.6782 (4)0.076 (2)
H25A0.6995−0.1760.64840.114*
H25B0.7879−0.19240.73910.114*
H25C0.8208−0.21170.64830.114*
C261.0042 (6)−0.1318 (4)0.7865 (4)0.078 (2)
H26A1.0682−0.14510.76160.117*
H26B0.9591−0.18090.78760.117*
H26C1.0314−0.11130.84630.117*
C271.0888 (5)0.0364 (5)0.7901 (4)0.0730 (18)
H27A1.1433−0.00510.78280.109*
H27B1.08370.0380.85150.109*
H27C1.11280.08990.77330.109*
C280.9492 (6)0.1650 (4)0.6799 (4)0.0728 (19)
H28A1.02360.16550.66710.109*
H28B0.95360.1890.73780.109*
H28C0.89730.19690.63540.109*
I10.87935 (3)0.06968 (3)0.43456 (2)0.05850 (16)
C290.2774 (6)0.4708 (4)0.3696 (4)0.0684 (17)
H290.29960.48020.3130.082*
Cl10.14519 (19)0.41957 (14)0.34585 (16)0.1030 (7)
Cl20.3802 (2)0.40834 (19)0.43583 (18)0.1351 (10)
Cl30.2678 (3)0.56550 (15)0.4179 (2)0.1352 (10)
U11U22U33U12U13U23
C10.037 (3)0.036 (3)0.036 (2)0.008 (2)0.008 (2)0.002 (2)
C20.046 (3)0.038 (3)0.030 (2)0.002 (2)0.006 (2)0.000 (2)
C30.057 (3)0.048 (3)0.044 (3)0.021 (3)0.012 (3)0.006 (2)
C40.065 (4)0.056 (4)0.055 (3)0.024 (3)0.024 (3)−0.005 (3)
C50.059 (3)0.056 (3)0.035 (3)0.008 (3)0.016 (2)0.002 (2)
C60.040 (3)0.036 (3)0.036 (3)0.000 (2)0.006 (2)0.001 (2)
C70.037 (3)0.041 (3)0.033 (2)0.014 (2)0.005 (2)0.007 (2)
C80.039 (3)0.047 (3)0.037 (3)0.007 (2)0.002 (2)0.006 (2)
C90.047 (3)0.053 (3)0.039 (3)0.011 (3)0.004 (2)0.000 (2)
C100.060 (3)0.054 (3)0.036 (3)0.016 (3)0.016 (3)0.008 (2)
C110.044 (3)0.049 (3)0.049 (3)0.006 (2)0.012 (2)0.015 (3)
C120.040 (3)0.041 (3)0.044 (3)0.006 (2)0.007 (2)0.003 (2)
C130.072 (4)0.064 (4)0.065 (4)−0.013 (3)0.009 (3)0.006 (3)
C140.104 (6)0.096 (5)0.044 (3)−0.010 (4)0.005 (4)−0.015 (4)
C150.104 (6)0.109 (6)0.046 (4)0.002 (5)0.028 (4)0.015 (4)
C160.084 (5)0.080 (5)0.077 (5)−0.008 (4)0.028 (4)0.025 (4)
C170.067 (4)0.072 (4)0.061 (4)−0.011 (3)0.006 (3)0.003 (3)
C180.039 (3)0.040 (3)0.031 (2)0.004 (2)0.008 (2)0.007 (2)
C190.047 (3)0.044 (3)0.029 (2)0.000 (2)0.011 (2)0.002 (2)
C200.067 (4)0.038 (3)0.039 (3)0.003 (2)0.018 (3)0.002 (2)
C210.057 (3)0.055 (3)0.038 (3)0.020 (3)0.017 (2)0.011 (2)
C220.042 (3)0.062 (4)0.035 (3)0.004 (2)0.010 (2)0.005 (2)
C230.049 (3)0.049 (3)0.033 (2)−0.003 (2)0.004 (2)0.004 (2)
C240.057 (4)0.060 (4)0.063 (4)−0.012 (3)0.010 (3)−0.006 (3)
C250.119 (6)0.037 (3)0.070 (4)−0.006 (3)0.019 (4)0.005 (3)
C260.079 (5)0.078 (5)0.073 (4)0.032 (4)0.008 (4)0.028 (4)
C270.049 (4)0.103 (5)0.059 (4)0.005 (3)−0.003 (3)0.011 (4)
C280.074 (4)0.065 (4)0.070 (4)−0.023 (3)−0.002 (3)0.008 (3)
I10.0572 (2)0.0742 (3)0.0485 (2)0.03317 (19)0.02111 (17)0.01532 (19)
C290.072 (4)0.068 (4)0.070 (4)0.006 (3)0.027 (3)0.014 (3)
Cl10.0842 (14)0.1114 (17)0.1078 (16)−0.0161 (12)0.0108 (12)0.0079 (13)
Cl20.0936 (17)0.165 (3)0.144 (2)0.0425 (16)0.0228 (16)0.0602 (19)
Cl30.160 (3)0.1012 (18)0.150 (2)−0.0052 (16)0.048 (2)−0.0496 (16)
C1—C61.392 (6)C16—H16C0.96
C1—C21.400 (6)C17—H17A0.96
C1—I12.099 (4)C17—H17B0.96
C2—C31.381 (6)C17—H17C0.96
C2—C71.501 (6)C18—C231.398 (7)
C3—C41.377 (7)C18—C191.406 (7)
C3—H30.93C19—C201.400 (7)
C4—C51.379 (7)C19—C241.503 (7)
C4—H40.93C20—C211.408 (8)
C5—C61.386 (7)C20—C251.507 (7)
C5—H50.93C21—C221.389 (7)
C6—C181.492 (6)C21—C261.514 (7)
C7—C121.394 (7)C22—C231.393 (7)
C7—C81.398 (7)C22—C271.518 (8)
C8—C91.403 (7)C23—C281.513 (7)
C8—C131.507 (7)C24—H24A0.96
C9—C101.386 (7)C24—H24B0.96
C9—C141.516 (8)C24—H24C0.96
C10—C111.389 (7)C25—H25A0.96
C10—C151.521 (7)C25—H25B0.96
C11—C121.401 (7)C25—H25C0.96
C11—C161.512 (8)C26—H26A0.96
C12—C171.520 (7)C26—H26B0.96
C13—H13A0.96C26—H26C0.96
C13—H13B0.96C27—H27A0.96
C13—H13C0.96C27—H27B0.96
C14—H14A0.96C27—H27C0.96
C14—H14B0.96C28—H28A0.96
C14—H14C0.96C28—H28B0.96
C15—H15A0.96C28—H28C0.96
C15—H15B0.96C29—Cl31.708 (7)
C15—H15C0.96C29—Cl21.729 (7)
C16—H16A0.96C29—Cl11.753 (7)
C16—H16B0.96C29—H290.98
C6—C1—C2122.3 (4)C12—C17—H17A109.5
C6—C1—I1119.4 (3)C12—C17—H17B109.5
C2—C1—I1118.3 (3)H17A—C17—H17B109.5
C3—C2—C1117.5 (4)C12—C17—H17C109.5
C3—C2—C7119.3 (4)H17A—C17—H17C109.5
C1—C2—C7123.2 (4)H17B—C17—H17C109.5
C4—C3—C2121.5 (5)C23—C18—C19120.6 (4)
C4—C3—H3119.3C23—C18—C6119.9 (4)
C2—C3—H3119.3C19—C18—C6119.5 (4)
C3—C4—C5119.8 (5)C20—C19—C18119.7 (5)
C3—C4—H4120.1C20—C19—C24121.9 (5)
C5—C4—H4120.1C18—C19—C24118.5 (4)
C4—C5—C6121.2 (5)C19—C20—C21119.0 (5)
C4—C5—H5119.4C19—C20—C25120.5 (5)
C6—C5—H5119.4C21—C20—C25120.4 (5)
C5—C6—C1117.7 (4)C22—C21—C20121.0 (5)
C5—C6—C18120.8 (4)C22—C21—C26119.6 (5)
C1—C6—C18121.5 (4)C20—C21—C26119.4 (5)
C12—C7—C8121.3 (4)C21—C22—C23120.0 (5)
C12—C7—C2120.2 (4)C21—C22—C27119.5 (5)
C8—C7—C2118.5 (4)C23—C22—C27120.5 (5)
C7—C8—C9118.3 (5)C22—C23—C18119.7 (5)
C7—C8—C13120.3 (5)C22—C23—C28120.9 (5)
C9—C8—C13121.3 (5)C18—C23—C28119.5 (5)
C10—C9—C8120.8 (5)C19—C24—H24A109.5
C10—C9—C14120.8 (5)C19—C24—H24B109.5
C8—C9—C14118.4 (5)H24A—C24—H24B109.5
C9—C10—C11120.3 (5)C19—C24—H24C109.5
C9—C10—C15120.2 (5)H24A—C24—H24C109.5
C11—C10—C15119.6 (5)H24B—C24—H24C109.5
C10—C11—C12120.0 (5)C20—C25—H25A109.5
C10—C11—C16120.3 (5)C20—C25—H25B109.5
C12—C11—C16119.7 (5)H25A—C25—H25B109.5
C7—C12—C11119.2 (5)C20—C25—H25C109.5
C7—C12—C17119.8 (5)H25A—C25—H25C109.5
C11—C12—C17121.0 (5)H25B—C25—H25C109.5
C8—C13—H13A109.5C21—C26—H26A109.5
C8—C13—H13B109.5C21—C26—H26B109.5
H13A—C13—H13B109.5H26A—C26—H26B109.5
C8—C13—H13C109.5C21—C26—H26C109.5
H13A—C13—H13C109.5H26A—C26—H26C109.5
H13B—C13—H13C109.5H26B—C26—H26C109.5
C9—C14—H14A109.5C22—C27—H27A109.5
C9—C14—H14B109.5C22—C27—H27B109.5
H14A—C14—H14B109.5H27A—C27—H27B109.5
C9—C14—H14C109.5C22—C27—H27C109.5
H14A—C14—H14C109.5H27A—C27—H27C109.5
H14B—C14—H14C109.5H27B—C27—H27C109.5
C10—C15—H15A109.5C23—C28—H28A109.5
C10—C15—H15B109.5C23—C28—H28B109.5
H15A—C15—H15B109.5H28A—C28—H28B109.5
C10—C15—H15C109.5C23—C28—H28C109.5
H15A—C15—H15C109.5H28A—C28—H28C109.5
H15B—C15—H15C109.5H28B—C28—H28C109.5
C11—C16—H16A109.5Cl3—C29—Cl2111.9 (4)
C11—C16—H16B109.5Cl3—C29—Cl1111.1 (4)
H16A—C16—H16B109.5Cl2—C29—Cl1110.0 (4)
C11—C16—H16C109.5Cl3—C29—H29107.9
H16A—C16—H16C109.5Cl2—C29—H29107.9
H16B—C16—H16C109.5Cl1—C29—H29107.9
C6—C1—C2—C30.3 (7)C2—C7—C12—C11−176.4 (4)
I1—C1—C2—C3−179.4 (4)C8—C7—C12—C17−176.9 (5)
C6—C1—C2—C7−177.9 (4)C2—C7—C12—C173.3 (7)
I1—C1—C2—C72.5 (6)C10—C11—C12—C7−2.0 (7)
C1—C2—C3—C40.5 (8)C16—C11—C12—C7178.1 (5)
C7—C2—C3—C4178.8 (5)C10—C11—C12—C17178.3 (5)
C2—C3—C4—C5−1.3 (9)C16—C11—C12—C17−1.5 (8)
C3—C4—C5—C61.3 (9)C5—C6—C18—C23−94.7 (6)
C4—C5—C6—C1−0.5 (8)C1—C6—C18—C2387.5 (6)
C4—C5—C6—C18−178.3 (5)C5—C6—C18—C1985.6 (6)
C2—C1—C6—C5−0.3 (7)C1—C6—C18—C19−92.2 (6)
I1—C1—C6—C5179.3 (4)C23—C18—C19—C20−1.4 (7)
C2—C1—C6—C18177.5 (4)C6—C18—C19—C20178.3 (4)
I1—C1—C6—C18−2.8 (6)C23—C18—C19—C24−179.5 (5)
C3—C2—C7—C1289.3 (6)C6—C18—C19—C240.2 (7)
C1—C2—C7—C12−92.5 (6)C18—C19—C20—C21−0.8 (7)
C3—C2—C7—C8−90.5 (6)C24—C19—C20—C21177.2 (5)
C1—C2—C7—C887.7 (6)C18—C19—C20—C25178.3 (5)
C12—C7—C8—C9−1.7 (7)C24—C19—C20—C25−3.7 (8)
C2—C7—C8—C9178.1 (4)C19—C20—C21—C221.5 (7)
C12—C7—C8—C13−179.9 (5)C25—C20—C21—C22−177.6 (5)
C2—C7—C8—C13−0.2 (7)C19—C20—C21—C26−178.1 (5)
C7—C8—C9—C10−1.4 (7)C25—C20—C21—C262.8 (8)
C13—C8—C9—C10176.8 (5)C20—C21—C22—C230.1 (7)
C7—C8—C9—C14−180.0 (5)C26—C21—C22—C23179.7 (5)
C13—C8—C9—C14−1.8 (8)C20—C21—C22—C27179.8 (5)
C8—C9—C10—C112.7 (8)C26—C21—C22—C27−0.6 (8)
C14—C9—C10—C11−178.7 (5)C21—C22—C23—C18−2.3 (7)
C8—C9—C10—C15−175.7 (5)C27—C22—C23—C18178.0 (5)
C14—C9—C10—C152.8 (8)C21—C22—C23—C28179.5 (5)
C9—C10—C11—C12−1.0 (8)C27—C22—C23—C28−0.2 (8)
C15—C10—C11—C12177.5 (5)C19—C18—C23—C223.0 (7)
C9—C10—C11—C16178.8 (5)C6—C18—C23—C22−176.7 (4)
C15—C10—C11—C16−2.7 (8)C19—C18—C23—C28−178.7 (5)
C8—C7—C12—C113.4 (7)C6—C18—C23—C281.5 (7)
Cg2 and C3 are the centroids of the C7–C12 and C18–C23 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
C26—H26A···Cg2i0.963.86 (1)2.97155
C28—H28A···Cg2ii0.963.53 (1)2.87127
C29—H29···Cg3iii0.983.42 (1)2.44177
YX···CgYXX···CgY···CgYX···Cg
C1—I1···Cg3i2.099 (4)3.975 (2)6.026 (5)164.67 (13)
Table 1

C—H⋯π inter­actions (Å, °)

Cg2 and C3 are the centroids of the C7–C12 and C18–C23 benzene rings, respectively.

D—H⋯AD—HH⋯ADAD—H⋯A
C26—H26ACg2i0.963.86 (1)2.97155
C28—H28ACg2ii0.963.53 (1)2.87127
C29—H29⋯Cg3iii0.983.42 (1)2.44177

Symmetry codes: (i) ; (ii) ; (iii) .

Table 2

C—I⋯π inter­actions (Å, °)

Cg3 is the centroid of the C18–C23 benzene ring.

YXCgYXXCgYCgYXCg
C1—I1⋯Cg3i2.099 (4)3.975 (2)6.026 (5)164.67 (13)

Symmetry code: (i) .

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1.  Synthesis of 2,6-diarylphenyldimethylsilyl cations: polar-pi distribution of cation character.

Authors:  Simon Duttwyler; Quyen-Quyen Do; Anthony Linden; Kim K Baldridge; Jay S Siegel
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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