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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1931.
Published online 2009 July 18. doi:  10.1107/S1600536809026932
PMCID: PMC2977480

2,2′-[(Biphenyl-4,4′-di­yl)di(ethene-1,2-di­yl)]dibenzene­sulfonic acid–4-methyl­piperidine–water (1/2/2)

Abstract

The title compound, C28H22O6S2·2C6H13N·2H2O, was prepared by the reaction of a Wittig reagent and 2-formyl­benzene­sulfonic acid. The main molecule lies about an inversion centre at the midpoint of the C—C bond between the inner benzene rings. The mol­ecular conformation is stabilized by intramolecular hydrogen bonds. The crystal structure is further stabilized by O—H(...)O and N—H(...)O hydrogen-bonding inter­actions.

Related literature

For the optical properties of ethyl­ene biphenyls, see: Song et al. (2003 [triangle]). For comparative bond lengths, see: Trueblood et al. (1982 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1931-scheme1.jpg

Experimental

Crystal data

  • C28H22O6S2·2(C6H13N)·2(H2O)
  • M r = 752.96
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1931-efi1.jpg
  • a = 14.852 (3) Å
  • b = 9.7240 (19) Å
  • c = 14.765 (3) Å
  • β = 109.76 (3)°
  • V = 2006.8 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 293 K
  • 0.26 × 0.21 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 4436 measured reflections
  • 4264 independent reflections
  • 1779 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.204
  • S = 1.01
  • 4264 reflections
  • 243 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026932/at2832sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026932/at2832Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Ethylene biphenyl have received considerable attention in the literature. They are attractive from several points of view, such as the optics characteristic. (Song et al., 2003). As part of our search for new ethylene biphenyl compounds we synthesized the title compound (I), and describe its structure here.

Main group of the title molecule in Fig. 1 has an inversion centre lied on the midpoint of the C—C bond between the inner benzene rings. The C7—C8 bond length of 1.326 (5)Å is comparable with C—C double bond [1.336 (2) Å] reported (Trueblood et al.,1982).

The molecular conformation is stabilized by C—H···O hydrogen bonds. The crystal structure is further stabilized by N—H···O hydrogen bonding interactions (Table 1).

Experimental

A mixture of the Wittig-reagent (0.1 mol), and 2-formylbenzenesulfonic acid (0.2 mol) was stirred in refluxing 4-methylpiperidine (20 mL) for 4 h to afford the title compound (0.084 mol, yield 84%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

The H atoms of the water molecule were found difference Fourier map and refined freely. The other atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93 - 0.97 Å O–H = 0.82 Å and with Uiso(H)=1.2–1.5Ueq (C, O).

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C28H22O6S2·2(C6H13N)·2(H2O)Z = 2
Mr = 752.96F(000) = 804
Monoclinic, P21/cDx = 1.246 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.852 (3) ŵ = 0.19 mm1
b = 9.7240 (19) ÅT = 293 K
c = 14.765 (3) ÅBlock, yellow
β = 109.76 (3)°0.26 × 0.21 × 0.18 mm
V = 2006.8 (7) Å3

Data collection

Bruker SMART CCD area-detector diffractometer1779 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 27.0°, θmin = 1.5°
[var phi] and ω scansh = −17→17
4436 measured reflectionsk = −11→0
4264 independent reflectionsl = 0→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0935P)2 + 0.2207P] where P = (Fo2 + 2Fc2)/3
4264 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.34 e Å3
1 restraintΔρmin = −0.27 e Å3

Special details

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)

xyzUiso*/Ueq
S10.16287 (7)0.72108 (11)0.45278 (7)0.0650 (4)
O10.11710 (19)0.6177 (3)0.49284 (19)0.0777 (8)
O20.2213 (2)0.8160 (3)0.5239 (2)0.0963 (10)
H2A0.18720.86100.54640.144*
O30.0962 (2)0.7896 (3)0.3708 (2)0.0946 (10)
C10.2421 (2)0.6277 (4)0.4076 (2)0.0547 (9)
C20.2274 (3)0.6354 (4)0.3096 (3)0.0685 (11)
H2B0.17890.69090.27040.082*
C30.2841 (3)0.5616 (5)0.2699 (3)0.0813 (13)
H3B0.27440.56890.20450.098*
C40.3556 (3)0.4763 (5)0.3275 (3)0.0797 (13)
H4A0.39180.42290.30040.096*
C50.3726 (3)0.4712 (4)0.4253 (3)0.0673 (11)
H5A0.42220.41640.46370.081*
C60.3174 (2)0.5464 (4)0.4686 (2)0.0549 (9)
C70.3396 (2)0.5464 (4)0.5737 (2)0.0572 (10)
H7A0.30730.61080.59790.069*
C80.4005 (2)0.4653 (4)0.6378 (3)0.0593 (10)
H8A0.42960.39580.61430.071*
C90.4261 (2)0.4755 (4)0.7428 (2)0.0527 (9)
C100.4910 (3)0.3842 (5)0.8026 (3)0.0808 (13)
H10A0.51640.31470.77520.097*
C110.5191 (3)0.3931 (5)0.9011 (3)0.0785 (13)
H11A0.56270.32920.93820.094*
C120.4847 (2)0.4936 (4)0.9467 (2)0.0502 (9)
C130.4184 (3)0.5858 (4)0.8868 (3)0.0680 (11)
H13A0.39270.65480.91420.082*
C140.3906 (3)0.5760 (4)0.7881 (3)0.0679 (11)
H14A0.34660.63900.75060.081*
C170.1822 (5)0.2643 (6)0.1068 (3)0.131 (2)
H17A0.12980.22620.12270.196*
H17B0.19700.35430.13460.196*
H17C0.23720.20600.13170.196*
C150.0653 (3)0.3594 (5)−0.0460 (4)0.0913 (15)
H15A0.07490.4489−0.01520.110*
H15B0.01270.3150−0.03270.110*
C160.0386 (3)0.3788 (6)−0.1540 (4)0.0992 (16)
H16A0.02160.2909−0.18630.119*
H16B−0.01630.4394−0.17730.119*
N20.1191 (3)0.4378 (4)−0.1755 (2)0.0859 (11)
H2C0.11670.5144−0.20530.103*
C180.2061 (4)0.3503 (5)−0.1398 (3)0.0917 (14)
H18A0.25820.3927−0.15540.110*
H18B0.19350.2609−0.17060.110*
C190.2335 (3)0.3339 (5)−0.0337 (3)0.0815 (13)
H19A0.25160.4229−0.00330.098*
H19B0.28900.2741−0.01110.098*
C200.1544 (3)0.2747 (4)−0.0032 (3)0.0777 (12)
H20A0.14100.1815−0.02970.093*
O1W−0.0458 (3)0.4739 (4)0.3645 (2)0.0939 (11)
H2−0.082 (3)0.537 (4)0.380 (3)0.074 (16)*
H10.009 (3)0.512 (7)0.410 (4)0.17 (3)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0645 (6)0.0621 (6)0.0658 (6)0.0026 (6)0.0188 (5)0.0124 (6)
O10.0773 (18)0.080 (2)0.090 (2)0.0010 (15)0.0466 (16)0.0174 (16)
O20.101 (2)0.0657 (19)0.117 (2)0.0039 (17)0.0292 (19)−0.0220 (18)
O30.090 (2)0.108 (2)0.0765 (19)0.0237 (19)0.0168 (16)0.0307 (18)
C10.048 (2)0.056 (2)0.054 (2)−0.0167 (18)0.0110 (17)0.0052 (18)
C20.061 (2)0.084 (3)0.054 (2)−0.018 (2)0.010 (2)0.009 (2)
C30.085 (3)0.105 (4)0.055 (3)−0.030 (3)0.025 (2)−0.006 (3)
C40.077 (3)0.096 (3)0.076 (3)−0.024 (3)0.039 (2)−0.019 (3)
C50.055 (2)0.085 (3)0.064 (3)−0.007 (2)0.022 (2)−0.001 (2)
C60.050 (2)0.060 (2)0.058 (2)−0.0139 (18)0.0220 (18)0.0004 (18)
C70.056 (2)0.061 (2)0.055 (2)0.0001 (19)0.0205 (19)0.0048 (18)
C80.053 (2)0.067 (3)0.060 (2)0.0047 (19)0.0217 (18)0.003 (2)
C90.048 (2)0.059 (2)0.053 (2)0.0041 (18)0.0196 (17)0.0057 (19)
C100.094 (3)0.086 (3)0.063 (3)0.044 (3)0.027 (2)0.006 (2)
C110.091 (3)0.084 (3)0.057 (3)0.045 (3)0.021 (2)0.012 (2)
C120.0452 (19)0.053 (2)0.0534 (19)0.0041 (18)0.0180 (17)0.0099 (19)
C130.070 (3)0.070 (3)0.061 (3)0.028 (2)0.017 (2)0.001 (2)
C140.063 (2)0.073 (3)0.059 (3)0.025 (2)0.009 (2)0.011 (2)
C170.210 (7)0.108 (4)0.075 (3)0.012 (4)0.051 (4)0.012 (3)
C150.091 (3)0.081 (3)0.123 (4)−0.013 (3)0.065 (3)0.010 (3)
C160.075 (3)0.100 (4)0.100 (4)−0.001 (3)0.001 (3)0.000 (3)
N20.106 (3)0.077 (2)0.075 (2)−0.001 (2)0.032 (2)0.020 (2)
C180.108 (4)0.088 (3)0.096 (4)0.005 (3)0.057 (3)−0.003 (3)
C190.075 (3)0.077 (3)0.086 (3)0.016 (2)0.019 (2)−0.010 (2)
C200.114 (4)0.055 (2)0.066 (3)−0.001 (3)0.033 (2)0.001 (2)
O1W0.108 (3)0.106 (3)0.068 (2)0.000 (2)0.030 (2)0.0108 (19)

Geometric parameters (Å, °)

S1—O31.442 (3)C12—C12i1.488 (6)
S1—O21.446 (3)C13—C141.377 (5)
S1—O11.447 (3)C13—H13A0.9300
S1—C11.784 (4)C14—H14A0.9300
O2—H2A0.8200C17—C201.537 (5)
C1—C21.392 (5)C17—H17A0.9600
C1—C61.417 (5)C17—H17B0.9600
C2—C31.378 (6)C17—H17C0.9600
C2—H2B0.9300C15—C201.504 (6)
C3—C41.389 (6)C15—C161.519 (6)
C3—H3B0.9300C15—H15A0.9700
C4—C51.379 (5)C15—H15B0.9700
C4—H4A0.9300C16—N21.455 (6)
C5—C61.404 (5)C16—H16A0.9700
C5—H5A0.9300C16—H16B0.9700
C6—C71.473 (5)N2—C181.487 (5)
C7—C81.326 (5)N2—H2C0.8600
C7—H7A0.9300C18—C191.488 (5)
C8—C91.469 (5)C18—H18A0.9700
C8—H8A0.9300C18—H18B0.9700
C9—C141.384 (5)C19—C201.508 (6)
C9—C101.387 (5)C19—H19A0.9700
C10—C111.373 (5)C19—H19B0.9700
C10—H10A0.9300C20—H20A0.9800
C11—C121.380 (5)O1W—H20.90 (4)
C11—H11A0.9300O1W—H10.94 (6)
C12—C131.402 (5)
O3—S1—O2112.82 (19)C12—C13—H13A119.4
O3—S1—O1112.34 (19)C13—C14—C9122.2 (3)
O2—S1—O1113.35 (19)C13—C14—H14A118.9
O3—S1—C1105.87 (18)C9—C14—H14A118.9
O2—S1—C1106.64 (17)C20—C17—H17A109.5
O1—S1—C1105.03 (16)C20—C17—H17B109.5
S1—O2—H2A109.5H17A—C17—H17B109.5
C2—C1—C6120.2 (4)C20—C17—H17C109.5
C2—C1—S1118.1 (3)H17A—C17—H17C109.5
C6—C1—S1121.7 (3)H17B—C17—H17C109.5
C3—C2—C1120.8 (4)C20—C15—C16113.0 (4)
C3—C2—H2B119.6C20—C15—H15A109.0
C1—C2—H2B119.6C16—C15—H15A109.0
C2—C3—C4120.0 (4)C20—C15—H15B109.0
C2—C3—H3B120.0C16—C15—H15B109.0
C4—C3—H3B120.0H15A—C15—H15B107.8
C5—C4—C3119.6 (4)N2—C16—C15109.6 (4)
C5—C4—H4A120.2N2—C16—H16A109.8
C3—C4—H4A120.2C15—C16—H16A109.8
C4—C5—C6122.0 (4)N2—C16—H16B109.8
C4—C5—H5A119.0C15—C16—H16B109.8
C6—C5—H5A119.0H16A—C16—H16B108.2
C5—C6—C1117.3 (3)C16—N2—C18112.2 (4)
C5—C6—C7121.5 (3)C16—N2—H2C123.9
C1—C6—C7121.2 (3)C18—N2—H2C123.9
C8—C7—C6127.4 (4)N2—C18—C19109.3 (3)
C8—C7—H7A116.3N2—C18—H18A109.8
C6—C7—H7A116.3C19—C18—H18A109.8
C7—C8—C9125.7 (4)N2—C18—H18B109.8
C7—C8—H8A117.2C19—C18—H18B109.8
C9—C8—H8A117.2H18A—C18—H18B108.3
C14—C9—C10116.1 (3)C18—C19—C20113.1 (4)
C14—C9—C8123.5 (3)C18—C19—H19A109.0
C10—C9—C8120.3 (3)C20—C19—H19A109.0
C11—C10—C9122.0 (4)C18—C19—H19B109.0
C11—C10—H10A119.0C20—C19—H19B109.0
C9—C10—H10A119.0H19A—C19—H19B107.8
C10—C11—C12122.1 (3)C15—C20—C19109.2 (3)
C10—C11—H11A118.9C15—C20—C17111.4 (4)
C12—C11—H11A118.9C19—C20—C17112.4 (4)
C11—C12—C13116.2 (3)C15—C20—H20A107.9
C11—C12—C12i123.0 (4)C19—C20—H20A107.9
C13—C12—C12i120.8 (4)C17—C20—H20A107.9
C14—C13—C12121.3 (3)H2—O1W—H190 (3)
C14—C13—H13A119.4

Symmetry codes: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1···O10.94 (6)1.95 (6)2.881 (5)171 (6)
N2—H2C···O1Wii0.862.232.767 (4)120
N2—H2C···O3iii0.862.282.787 (5)117
C2—H2B···O30.932.422.838 (5)107
C7—H7A···O20.932.423.103 (5)130

Symmetry codes: (ii) −x, −y+1, −z; (iii) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2832).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, H. C., Xu, X. H. & Liu, G. R. (2003). Chin. Chem. Res.14, 1–5.
  • Trueblood, K., Mirsky, K., Maverick, E., Knobler, C. & Grossenbacher, L. (1982). Acta Cryst. B38, 2428–2435.

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