Literature DB >> 21578931

Benzhydryl phenyl sulfone.

Mahiuddin Baidya1, Herbert Mayr, Peter Mayer.   

Abstract

In the title compound, C(19)H(16)O(2)S, the sulfur-bound phenyl group is approximately parallel to one of the two phenyl rings of the benzhydryl group, making a dihedral angle of 12.53 (10)°, and forms a dihedral angle of 41.25 (9)° with the other phenyl ring. In the crystal, weak C-H⋯O inter-actions form a two-dimensional network propagating along the bc plane.

Entities:  

Year:  2009        PMID： 21578931      PMCID： PMC2972123          DOI： 10.1107/S1600536809050363

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


Related literature

For background to the sulfone anion, see: da Silva Corrêa et al. (1968 ▶); Mayr et al. (2001 ▶, 2008 ▶). For a related structure, see: Li et al. (2005 ▶). For graph-set analysis of hydrogen-bond networks, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C19H16O2S M = 308.40 Orthorhombic, a = 16.3250 (4) Å b = 5.7979 (1) Å c = 16.4983 (4) Å V = 1561.58 (6) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 200 K 0.20 × 0.10 × 0.09 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: none 11675 measured reflections 3499 independent reflections 3136 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.075 S = 1.04 3499 reflections 199 parameters 1 restraint H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.28 e Å−3 Absolute structure: Flack (1983 ▶), 1646 Friedel pairs Flack parameter: −0.03 (6) Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050363/ds2011sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050363/ds2011Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H16O2SF(000) = 648
Mr = 308.40Dx = 1.312 (1) Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6504 reflections
a = 16.3250 (4) Åθ = 3.1–27.5°
b = 5.7979 (1) ŵ = 0.21 mm−1
c = 16.4983 (4) ÅT = 200 K
V = 1561.58 (6) Å3Rod, colourless
Z = 40.20 × 0.10 × 0.09 mm
Nonius KappaCCD diffractometer3136 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.027
MONTEL, graded multilayered X-ray opticsθmax = 27.5°, θmin = 3.5°
Detector resolution: 9 pixels mm-1h = −21→21
CCD; rotation images; thick slices, phi/ω–scank = −7→6
11675 measured reflectionsl = −21→20
3499 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.075w = 1/[σ2(Fo2) + (0.0396P)2 + 0.2163P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3499 reflectionsΔρmax = 0.14 e Å−3
199 parametersΔρmin = −0.28 e Å−3
1 restraintAbsolute structure: Flack (1983), 1646 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.03 (6)
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 > 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
S10.06340 (2)0.12898 (6)0.26302 (3)0.02887 (10)
O10.08669 (8)0.1945 (2)0.34378 (7)0.0408 (3)
O20.03981 (7)−0.10715 (19)0.24877 (8)0.0384 (3)
C1−0.01788 (10)0.3229 (3)0.23092 (10)0.0276 (3)
H10.00340.48200.24090.033*
C2−0.03155 (9)0.3073 (3)0.14009 (10)0.0272 (3)
C3−0.06491 (11)0.1160 (3)0.10143 (11)0.0347 (4)
H3−0.0816−0.01390.13240.042*
C4−0.07391 (11)0.1141 (3)0.01781 (12)0.0405 (4)
H4−0.0964−0.0180−0.00800.049*
C5−0.05082 (12)0.2999 (4)−0.02807 (12)0.0428 (4)
H5−0.05760.2970−0.08530.051*
C6−0.01740 (12)0.4927 (4)0.00955 (13)0.0451 (5)
H6−0.00080.6218−0.02180.054*
C7−0.00847 (11)0.4955 (3)0.09276 (11)0.0363 (4)
H70.01380.62830.11820.044*
C8−0.09145 (10)0.2969 (3)0.28610 (9)0.0304 (4)
C9−0.14154 (12)0.1021 (3)0.28814 (12)0.0431 (4)
H9−0.1290−0.02740.25510.052*
C10−0.20970 (13)0.0971 (4)0.33832 (13)0.0500 (5)
H10−0.2444−0.03430.33830.060*
C11−0.22748 (13)0.2805 (4)0.38811 (13)0.0531 (5)
H11−0.27400.27510.42270.064*
C12−0.17763 (14)0.4719 (4)0.38771 (14)0.0547 (5)
H12−0.18950.59850.42230.066*
C13−0.10994 (12)0.4802 (3)0.33668 (11)0.0406 (4)
H13−0.07600.61330.33650.049*
C140.14411 (10)0.2005 (3)0.19613 (10)0.0292 (3)
C150.18653 (11)0.4044 (3)0.20890 (12)0.0407 (4)
H150.17390.50020.25390.049*
C160.24784 (12)0.4662 (3)0.15468 (14)0.0479 (5)
H160.27750.60550.16230.057*
C170.26549 (12)0.3259 (4)0.09010 (13)0.0503 (5)
H170.30750.36910.05320.060*
C180.22315 (13)0.1231 (4)0.07798 (14)0.0517 (5)
H180.23640.02670.03330.062*
C190.16122 (12)0.0598 (3)0.13093 (12)0.0403 (4)
H190.1311−0.07820.12240.048*
U11U22U33U12U13U23
S10.03180 (18)0.02898 (18)0.02584 (18)0.00027 (14)−0.00044 (18)0.00176 (17)
O10.0447 (7)0.0530 (8)0.0247 (6)0.0025 (6)−0.0042 (5)0.0005 (5)
O20.0408 (6)0.0273 (6)0.0471 (9)−0.0006 (4)0.0029 (6)0.0047 (5)
C10.0315 (8)0.0251 (8)0.0263 (8)−0.0019 (6)0.0000 (7)−0.0014 (6)
C20.0257 (7)0.0301 (8)0.0258 (8)0.0028 (6)0.0008 (6)0.0011 (6)
C30.0384 (9)0.0357 (9)0.0301 (9)−0.0062 (7)−0.0017 (7)−0.0001 (7)
C40.0394 (9)0.0507 (11)0.0312 (10)−0.0053 (8)−0.0032 (8)−0.0060 (8)
C50.0423 (10)0.0597 (12)0.0262 (9)0.0046 (9)−0.0005 (8)0.0006 (8)
C60.0561 (13)0.0471 (11)0.0321 (9)0.0014 (9)0.0063 (9)0.0098 (7)
C70.0440 (10)0.0316 (9)0.0334 (9)−0.0002 (7)0.0045 (7)0.0013 (7)
C80.0327 (8)0.0324 (8)0.0261 (9)0.0015 (6)−0.0017 (6)0.0028 (6)
C90.0433 (10)0.0450 (11)0.0410 (11)−0.0093 (8)0.0040 (8)−0.0017 (8)
C100.0403 (10)0.0638 (13)0.0460 (12)−0.0138 (9)0.0040 (9)0.0146 (10)
C110.0409 (10)0.0738 (14)0.0445 (12)0.0098 (10)0.0133 (9)0.0159 (11)
C120.0575 (13)0.0597 (13)0.0470 (12)0.0113 (10)0.0174 (10)−0.0022 (10)
C130.0465 (10)0.0412 (10)0.0340 (10)0.0044 (8)0.0048 (8)−0.0049 (8)
C140.0270 (8)0.0333 (8)0.0273 (8)0.0008 (6)−0.0026 (7)0.0016 (7)
C150.0384 (10)0.0429 (10)0.0409 (11)−0.0064 (8)−0.0044 (8)−0.0039 (8)
C160.0340 (9)0.0507 (11)0.0589 (13)−0.0111 (9)−0.0065 (9)0.0088 (10)
C170.0320 (9)0.0683 (13)0.0505 (12)0.0027 (9)0.0089 (9)0.0144 (10)
C180.0466 (11)0.0625 (13)0.0459 (12)0.0048 (9)0.0128 (10)−0.0074 (10)
C190.0402 (9)0.0394 (9)0.0414 (11)0.0016 (8)0.0045 (8)−0.0056 (8)
S1—O11.4366 (13)C9—C101.387 (3)
S1—O21.4415 (12)C9—H90.9500
S1—C141.7681 (17)C10—C111.374 (3)
S1—C11.8180 (16)C10—H100.9500
C1—C81.514 (2)C11—C121.376 (3)
C1—C21.518 (2)C11—H110.9500
C1—H11.0000C12—C131.390 (3)
C2—C31.390 (2)C12—H120.9500
C2—C71.394 (2)C13—H130.9500
C3—C41.387 (3)C14—C191.379 (2)
C3—H30.9500C14—C151.386 (2)
C4—C51.369 (3)C15—C161.389 (3)
C4—H40.9500C15—H150.9500
C5—C61.390 (3)C16—C171.371 (3)
C5—H50.9500C16—H160.9500
C6—C71.381 (3)C17—C181.378 (3)
C6—H60.9500C17—H170.9500
C7—H70.9500C18—C191.386 (3)
C8—C131.385 (2)C18—H180.9500
C8—C91.395 (3)C19—H190.9500
O1—S1—O2118.23 (7)C10—C9—C8120.08 (19)
O1—S1—C14108.64 (8)C10—C9—H9120.0
O2—S1—C14108.67 (8)C8—C9—H9120.0
O1—S1—C1107.45 (8)C11—C10—C9120.67 (19)
O2—S1—C1110.16 (7)C11—C10—H10119.7
C14—S1—C1102.53 (8)C9—C10—H10119.7
C8—C1—C2118.10 (14)C10—C11—C12119.74 (19)
C8—C1—S1110.02 (11)C10—C11—H11120.1
C2—C1—S1110.99 (11)C12—C11—H11120.1
C8—C1—H1105.6C11—C12—C13120.05 (19)
C2—C1—H1105.6C11—C12—H12120.0
S1—C1—H1105.6C13—C12—H12120.0
C3—C2—C7118.25 (15)C8—C13—C12120.79 (18)
C3—C2—C1123.92 (15)C8—C13—H13119.6
C7—C2—C1117.83 (14)C12—C13—H13119.6
C4—C3—C2120.27 (16)C19—C14—C15121.46 (17)
C4—C3—H3119.9C19—C14—S1119.94 (13)
C2—C3—H3119.9C15—C14—S1118.53 (13)
C5—C4—C3120.94 (18)C14—C15—C16118.82 (18)
C5—C4—H4119.5C14—C15—H15120.6
C3—C4—H4119.5C16—C15—H15120.6
C4—C5—C6119.59 (18)C17—C16—C15119.91 (18)
C4—C5—H5120.2C17—C16—H16120.0
C6—C5—H5120.2C15—C16—H16120.0
C7—C6—C5119.67 (18)C16—C17—C18120.89 (19)
C7—C6—H6120.2C16—C17—H17119.6
C5—C6—H6120.2C18—C17—H17119.6
C6—C7—C2121.27 (17)C17—C18—C19120.03 (19)
C6—C7—H7119.4C17—C18—H18120.0
C2—C7—H7119.4C19—C18—H18120.0
C13—C8—C9118.64 (17)C14—C19—C18118.88 (18)
C13—C8—C1117.33 (15)C14—C19—H19120.6
C9—C8—C1124.03 (15)C18—C19—H19120.6
O1—S1—C1—C8−61.76 (13)C13—C8—C9—C101.9 (3)
O2—S1—C1—C868.31 (13)C1—C8—C9—C10−177.35 (17)
C14—S1—C1—C8−176.16 (11)C8—C9—C10—C11−1.8 (3)
O1—S1—C1—C2165.65 (11)C9—C10—C11—C120.6 (3)
O2—S1—C1—C2−64.28 (13)C10—C11—C12—C130.5 (3)
C14—S1—C1—C251.25 (12)C9—C8—C13—C12−0.9 (3)
C8—C1—C2—C3−59.0 (2)C1—C8—C13—C12178.46 (18)
S1—C1—C2—C369.33 (18)C11—C12—C13—C8−0.3 (3)
C8—C1—C2—C7121.61 (17)O1—S1—C14—C19144.32 (14)
S1—C1—C2—C7−110.03 (15)O2—S1—C14—C1914.45 (16)
C7—C2—C3—C40.6 (3)C1—S1—C14—C19−102.16 (15)
C1—C2—C3—C4−178.76 (17)O1—S1—C14—C15−38.52 (16)
C2—C3—C4—C5−0.5 (3)O2—S1—C14—C15−168.39 (13)
C3—C4—C5—C60.4 (3)C1—S1—C14—C1575.01 (15)
C4—C5—C6—C7−0.5 (3)C19—C14—C15—C16−0.3 (3)
C5—C6—C7—C20.7 (3)S1—C14—C15—C16−177.45 (15)
C3—C2—C7—C6−0.7 (3)C14—C15—C16—C17−0.2 (3)
C1—C2—C7—C6178.68 (17)C15—C16—C17—C180.0 (3)
C2—C1—C8—C13−120.05 (16)C16—C17—C18—C190.7 (3)
S1—C1—C8—C13111.14 (15)C15—C14—C19—C181.0 (3)
C2—C1—C8—C959.2 (2)S1—C14—C19—C18178.09 (15)
S1—C1—C8—C9−69.59 (19)C17—C18—C19—C14−1.2 (3)
D—H···AD—HH···AD···AD—H···A
C1—H1···O2i1.002.463.449 (2)171
C4—H4···O1ii0.952.663.390 (2)134
C7—H7···O2i0.952.683.543 (2)152
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C1—H1⋯O2i 1.002.463.449 (2)171
C4—H4⋯O1ii 0.952.663.390 (2)134
C7—H7⋯O2i 0.952.683.543 (2)152

Symmetry codes: (i) ; (ii) .

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