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Iso­propyl 2,4,6-triiso­propyl­phenyl sulfone, C18H30O2S, (I), has been synthesized for the first time. In spite of the bulky iso­propyl substituents on both ortho positions, crystalline (I) does not exhibit rotational disorder of the iso­propyl group bonded to the sulfonyl. In contrast, the corresponding bromo- and chloro­iso­propyl groups of crystalline aryl sulfones possessing much smaller di-ortho-methyl substituents display striking rotational disorder. While the aryl rings of the latter compounds are essentially planar, considerable atom deviation from the aromatic least-squares plane of (I) was observed. None of the intra- or intermolecular distances between the methyl C atoms of the sulfonyl­iso­propyl group and those of the two ortho-iso­propyl groups of (I) is shorter than the sum of their van der Waals radii, making it unlikely that they would interfere with the rotation of the α-iso­propyl group prior to crystallization.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004635/om6220sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004635/om6220Isup2.hkl
Contains datablock I

CCDC reference: 238779

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.134
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.34 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.54 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C8 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN (Molecular Structure Corporation, 1997) and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: TEXSAN, SHELXL97 and PLATON (Spek, 2003).

2,4,6-Triisopropylphenyl isopropyl sulfone top
Crystal data top
C18H30O2SDx = 1.092 Mg m3
Mr = 310.49Melting point = 393–395 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7039 reflections
a = 17.4705 (6) Åθ = 2.4–25.1°
b = 11.5964 (4) ŵ = 0.17 mm1
c = 18.6412 (7) ÅT = 295 K
V = 3776.6 (2) Å3Rectangular, colorless
Z = 80.44 × 0.31 × 0.10 mm
F(000) = 1360
Data collection top
Bruker SMART CCD area-detector
diffractometer
2530 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.048
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
φ and ω scansh = 2020
47817 measured reflectionsk = 1313
3319 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0682P)2 + 1.2339P]
where P = (Fo2 + 2Fc2)/3
3319 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.22 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.26750 (3)0.18789 (4)0.68743 (3)0.0530 (2)
O10.29869 (9)0.26676 (13)0.73887 (9)0.0719 (5)
O20.19212 (9)0.21430 (15)0.66199 (9)0.0729 (5)
C10.33006 (11)0.17647 (16)0.61105 (11)0.0482 (5)
C20.40502 (12)0.22266 (17)0.61247 (12)0.0528 (5)
C30.44467 (13)0.22577 (19)0.54772 (13)0.0620 (6)
C40.41564 (14)0.18375 (19)0.48372 (13)0.0639 (6)
C50.34502 (14)0.13205 (19)0.48617 (12)0.0623 (6)
C60.30062 (12)0.12626 (17)0.54746 (11)0.0543 (5)
C70.44725 (13)0.2693 (2)0.67762 (13)0.0650 (6)
C80.46094 (18)0.1940 (3)0.41454 (16)0.0896 (9)
C90.22496 (13)0.0613 (2)0.54023 (13)0.0647 (6)
C100.26564 (12)0.04734 (18)0.72788 (12)0.0566 (5)
C110.21031 (17)0.0509 (3)0.79086 (15)0.0884 (8)
C120.34410 (14)0.0074 (2)0.74870 (16)0.0807 (8)
C130.52705 (16)0.2171 (3)0.68480 (17)0.0924 (9)
C140.45244 (18)0.4007 (2)0.67426 (18)0.0953 (9)
C150.5264 (3)0.1173 (3)0.4121 (2)0.161 (2)
C160.4773 (2)0.3159 (3)0.39546 (18)0.1190 (13)
C170.17231 (17)0.1174 (3)0.48514 (17)0.0927 (9)
C180.23945 (17)0.0643 (2)0.52107 (17)0.0885 (8)
H30.49340.25790.54740.074*
H50.32600.09910.44430.075*
H70.41790.24850.72050.078*
H80.42640.16610.37690.107*
H90.19910.06340.58690.078*
H100.24530.00700.69240.068*
H11A0.20650.02450.81180.133*
H11B0.16080.07490.77440.133*
H11C0.22870.10440.82610.133*
H12A0.36330.05510.78670.121*
H12B0.37760.01270.70800.121*
H12C0.34170.07120.76470.121*
H13A0.52350.13450.68310.139*
H13B0.54910.24020.72970.139*
H13C0.55870.24370.64610.139*
H14A0.48110.42300.63260.143*
H14B0.47760.42890.71650.143*
H14C0.40190.43270.67150.143*
H15A0.55790.13680.37160.241*
H15B0.50910.03910.40750.241*
H15C0.55560.12520.45540.241*
H16A0.50860.35020.43200.178*
H16B0.43000.35770.39170.178*
H16C0.50380.31860.35040.178*
H17A0.19570.11370.43860.139*
H17B0.16380.19650.49800.139*
H17C0.12430.07720.48420.139*
H18A0.19190.10580.52150.133*
H18B0.27380.09770.55550.133*
H18C0.26180.06880.47410.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0484 (3)0.0481 (3)0.0625 (3)0.0044 (2)0.0085 (2)0.0013 (2)
O10.0747 (11)0.0610 (9)0.0800 (11)0.0046 (8)0.0145 (9)0.0197 (8)
O20.0519 (9)0.0819 (11)0.0848 (11)0.0193 (8)0.0067 (8)0.0055 (9)
C10.0464 (11)0.0425 (11)0.0558 (12)0.0025 (9)0.0054 (9)0.0055 (9)
C20.0505 (12)0.0439 (11)0.0639 (13)0.0006 (9)0.0031 (10)0.0052 (10)
C30.0502 (12)0.0575 (13)0.0782 (16)0.0057 (10)0.0128 (11)0.0092 (12)
C40.0691 (15)0.0575 (13)0.0650 (14)0.0017 (12)0.0150 (12)0.0024 (11)
C50.0712 (15)0.0587 (13)0.0569 (13)0.0046 (11)0.0060 (11)0.0030 (11)
C60.0535 (12)0.0475 (12)0.0619 (13)0.0008 (9)0.0032 (10)0.0030 (10)
C70.0547 (13)0.0687 (15)0.0715 (15)0.0087 (11)0.0012 (11)0.0005 (12)
C80.102 (2)0.088 (2)0.0790 (18)0.0102 (16)0.0381 (16)0.0005 (15)
C90.0605 (14)0.0671 (15)0.0666 (14)0.0122 (11)0.0002 (11)0.0019 (11)
C100.0567 (13)0.0530 (12)0.0602 (13)0.0026 (10)0.0076 (10)0.0032 (10)
C110.095 (2)0.088 (2)0.0825 (18)0.0049 (16)0.0356 (15)0.0132 (15)
C120.0739 (17)0.0729 (16)0.0952 (19)0.0118 (13)0.0002 (15)0.0195 (15)
C130.0650 (17)0.115 (2)0.098 (2)0.0022 (16)0.0154 (15)0.0072 (18)
C140.094 (2)0.0752 (18)0.117 (2)0.0159 (15)0.0115 (17)0.0165 (17)
C150.205 (5)0.113 (3)0.164 (4)0.054 (3)0.118 (4)0.020 (3)
C160.161 (3)0.106 (3)0.090 (2)0.005 (2)0.043 (2)0.0300 (19)
C170.0732 (17)0.098 (2)0.106 (2)0.0022 (16)0.0216 (16)0.0008 (18)
C180.095 (2)0.0620 (16)0.109 (2)0.0218 (14)0.0021 (17)0.0015 (15)
Geometric parameters (Å, º) top
S1—O21.4328 (16)C10—H100.9800
S1—O11.4328 (16)C11—H11A0.9600
S1—C101.796 (2)C11—H11B0.9600
S1—C11.800 (2)C11—H11C0.9600
C1—C21.415 (3)C12—H12A0.9600
C1—C61.417 (3)C12—H12B0.9600
C2—C31.392 (3)C12—H12C0.9600
C2—C71.520 (3)C13—H13A0.9600
C3—C41.385 (3)C13—H13B0.9600
C4—C51.373 (3)C13—H13C0.9600
C4—C81.518 (3)C14—H14A0.9600
C5—C61.383 (3)C14—H14B0.9600
C6—C91.527 (3)C14—H14C0.9600
C7—C131.526 (3)C15—H15A0.9600
C7—C141.527 (4)C15—H15B0.9600
C8—C151.450 (4)C15—H15C0.9600
C8—C161.486 (4)C16—H16A0.9600
C9—C181.522 (3)C16—H16B0.9600
C9—C171.524 (4)C16—H16C0.9600
C10—C121.498 (3)C17—H17A0.9600
C10—C111.521 (3)C17—H17B0.9600
C3—H30.9300C17—H17C0.9600
C5—H50.9300C18—H18A0.9600
C7—H70.9800C18—H18B0.9600
C8—H80.9800C18—H18C0.9600
C9—H90.9800
O2—S1—O1115.76 (10)C10—C11—H11A109.5
O2—S1—C10108.43 (10)C10—C11—H11B109.5
O1—S1—C10107.77 (10)H11A—C11—H11B109.5
O2—S1—C1108.18 (10)C10—C11—H11C109.5
O1—S1—C1110.21 (10)H11A—C11—H11C109.5
C10—S1—C1106.04 (9)H11B—C11—H11C109.5
C2—C1—C6120.47 (19)C10—C12—H12A109.5
C3—C2—C1117.0 (2)C10—C12—H12B109.5
C4—C3—C2123.8 (2)H12A—C12—H12B109.5
C5—C4—C3117.0 (2)C10—C12—H12C109.5
C4—C5—C6123.6 (2)H12A—C12—H12C109.5
C5—C6—C1117.88 (19)H12B—C12—H12C109.5
C2—C1—S1121.28 (16)C7—C13—H13A109.5
C6—C1—S1118.14 (15)C7—C13—H13B109.5
C3—C2—C7116.22 (19)H13A—C13—H13B109.5
C1—C2—C7126.78 (19)C7—C13—H13C109.5
C5—C4—C8122.1 (2)H13A—C13—H13C109.5
C3—C4—C8120.9 (2)H13B—C13—H13C109.5
C5—C6—C9115.9 (2)C7—C14—H14A109.5
C1—C6—C9126.19 (19)C7—C14—H14B109.5
C2—C7—C13111.9 (2)H14A—C14—H14B109.5
C2—C7—C14110.5 (2)C7—C14—H14C109.5
C13—C7—C14110.2 (2)H14A—C14—H14C109.5
C15—C8—C16115.1 (3)H14B—C14—H14C109.5
C15—C8—C4113.0 (3)C8—C15—H15A109.5
C16—C8—C4112.2 (2)C8—C15—H15B109.5
C18—C9—C17110.5 (2)H15A—C15—H15B109.5
C18—C9—C6110.4 (2)C8—C15—H15C109.5
C17—C9—C6111.8 (2)H15A—C15—H15C109.5
C12—C10—C11112.9 (2)H15B—C15—H15C109.5
C12—C10—S1111.89 (16)C8—C16—H16A109.5
C11—C10—S1108.13 (16)C8—C16—H16B109.5
C4—C3—H3118.1H16A—C16—H16B109.5
C2—C3—H3118.1C8—C16—H16C109.5
C4—C5—H5118.2H16A—C16—H16C109.5
C6—C5—H5118.2H16B—C16—H16C109.5
C2—C7—H7108.0C9—C17—H17A109.5
C13—C7—H7108.0C9—C17—H17B109.5
C14—C7—H7108.0H17A—C17—H17B109.5
C15—C8—H8105.1C9—C17—H17C109.5
C16—C8—H8105.1H17A—C17—H17C109.5
C4—C8—H8105.1H17B—C17—H17C109.5
C18—C9—H9108.0C9—C18—H18A109.5
C17—C9—H9108.0C9—C18—H18B109.5
C6—C9—H9108.0H18A—C18—H18B109.5
C12—C10—H10107.9C9—C18—H18C109.5
C11—C10—H10107.9H18A—C18—H18C109.5
S1—C10—H10107.9H18B—C18—H18C109.5
O2—S1—C1—C2139.12 (17)C2—C1—C6—C9172.61 (19)
O1—S1—C1—C211.64 (19)S1—C1—C6—C911.3 (3)
C10—S1—C1—C2104.74 (17)C3—C2—C7—C1350.2 (3)
O2—S1—C1—C636.94 (18)C1—C2—C7—C13129.6 (2)
O1—S1—C1—C6164.41 (15)C3—C2—C7—C1473.0 (3)
C10—S1—C1—C679.21 (17)C1—C2—C7—C14107.2 (3)
C6—C1—C2—C35.7 (3)C5—C4—C8—C15107.5 (4)
S1—C1—C2—C3170.23 (15)C3—C4—C8—C1571.8 (4)
C6—C1—C2—C7174.1 (2)C5—C4—C8—C16120.3 (3)
S1—C1—C2—C79.9 (3)C3—C4—C8—C1660.3 (4)
C1—C2—C3—C41.8 (3)C5—C6—C9—C1862.2 (3)
C7—C2—C3—C4178.0 (2)C1—C6—C9—C18115.3 (3)
C2—C3—C4—C52.9 (3)C5—C6—C9—C1761.3 (3)
C2—C3—C4—C8177.7 (2)C1—C6—C9—C17121.2 (2)
C3—C4—C5—C63.9 (3)O2—S1—C10—C12173.69 (17)
C8—C4—C5—C6176.7 (2)O1—S1—C10—C1260.3 (2)
C4—C5—C6—C10.1 (3)C1—S1—C10—C1257.7 (2)
C4—C5—C6—C9177.8 (2)O2—S1—C10—C1161.3 (2)
C2—C1—C6—C54.9 (3)O1—S1—C10—C1164.69 (19)
S1—C1—C6—C5171.22 (16)C1—S1—C10—C11177.30 (18)
Deviation of atoms from phenyl least-squares plane (Å) top
AtomDeviation
C10.035 (2)
C2-0.024 (2)
C3-0.007 (2)
C40.027 (2)
C5-0.017 (2)
C6-0.014 (2)
S1*0.281 (1)
C7*-0.108 (2)
C8*0.096 (3)
C9*-0.120 (2)
Note: the asterisk (*) indicates that the atom was not used in the least-squares-plane calculation.
 

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