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ISSN: 2056-9890

4-(4-Cyano-2-fluoro­phen­­oxy)phenyl 4-methyl­benzene­sulfonate

aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
*Correspondence e-mail: lsp96@163.com

(Received 13 July 2009; accepted 23 July 2009; online 29 July 2009)

The title compound, C20H14FNO4S, was synthesized from hydro­quinone, p-toluene­sulfonyl chloride and 3,4-difluoro­benzonitrile. A folded conformation is adopted by the crystal structure. Inter­molecular C—H⋯N hydrogen bonds form dimers arranged around inversion centers.

Related literature

For the herbicidal activity of hydro­quinone derivatives, see: Bao et al. (2007[Bao, W. J., Wu, Y. G., Mao, C. H., Chen, M. & Huang, M. Z. (2007). Fine Chem. Interm. 37, 9-13.]); Liu (2002[Liu, C. L. (2002). Pesticides, 41, 38.]). For related structures, see: Chen & Zhang (2009[Chen, Y.-S. & Zhang, J.-H. (2009). Acta Cryst. E65, o767.]); Han et al. (2008[Han, J.-R., Tian, X., Zhen, X.-L., Li, Z.-C. & Liu, S.-X. (2008). Acta Cryst. E64, o2244.]); Yang et al. (2008[Yang, S.-P., Wang, D.-Q., Han, L.-J. & Liu, Y.-F. (2008). Acta Cryst. E64, o2088.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C20H14FNO4S

  • Mr = 383.39

  • Triclinic, [P \overline 1]

  • a = 7.5504 (4) Å

  • b = 9.9558 (6) Å

  • c = 12.5862 (6) Å

  • α = 89.5250 (15)°

  • β = 77.8080 (12)°

  • γ = 81.9370 (15)°

  • V = 915.40 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 296 K

  • 0.42 × 0.32 × 0.28 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.910, Tmax = 0.942

  • 9012 measured reflections

  • 4114 independent reflections

  • 2386 reflections with F2 > 2σ(F2)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.123

  • S = 1.01

  • 4114 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.50 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C16—H16⋯N1i 0.93 2.61 3.461 (3) 152
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004[Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]), and Larson (1970[Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: CrystalStructure.

Supporting information


Comment top

The herbicidal activity of hydroquinone derivatives is well known in the art (Liu, 2002. Bao et al., 2007). As part of our ongoing studies, we now describe the synthesis and the crystal structure of the title compound.

As shown in Fig.1, the terminal C1—C7/S1 phenyl ring, the central benzene ring (C8—C13/O3/O4) and the other terminal phenyl ring (C14—C20/N1) form three planes, with max deviations for fitted atoms of 0.042 Å, 0.022Å and 0.013 Å, respectively. These planes make dihedral angles of 45.0 (1)° and 64.6 (6)° respectively. Otherwise, the molecule is bent at the sulfonate group with the C1—S1—O3—C8 torsion angle of 50.7 (3). The other bond parameters are similar to those observed in 4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate (Yang et al., 2008), (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) iminomethyl]phenyl 4-bromobenzenesulfonate (Han et al., 2008) and 2-Methyl-3-nitrobenzyl cyanide (Chen et al., 2009).

In the crystal structure, the molecules are linked to form pseudo dimers by inter molecular C—H···N hydrogen bonds generating a graph set motif R22(10) (Table 1, Fig.2) (Etter, 1990, Bernstein et al., 1995). In addition, the structure is stabilized by weak C—H···O and van der Waal's interactions.

Related literature top

For the herbicidal activity of hydroquinone derivatives, see: Bao et al. (2007); Liu (2002). For related structures, see: Chen & Zhang (2009); Han et al. (2008); Yang et al. (2008). Forhydrogen-bond motifs, see: Bernstein et al. (1995); Etter (1990).

Experimental top

A DMSO (10 ml) solution of hydroquinone and p-toluenesulfonyl chloride in the presence of KOH as base was stirred at room temperature for 48 h. Then the mixture was heated to 70°C and 3,4-difluorobenzonitrile was added dropwise. Finally the mixture was washed with water (20 ml) and extracted with ethyl acetate (three times). The organic solvent was removed under reduced pressure and the product was purified by silica gel chromatography (pentane: ethyl acetate mixtures). Suitable crystals were obtained by slow evaporation of ethanol at room temperature.

Refinement top

All H atoms were placed in calculated positions with C—H = 0.93–0.98 Å, and were included in the refinement in the riding model with Uiso(H) = 1.2Ueq of the carrier atoms.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004), and Larson (1970); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top
[Figure 1] Fig. 1. Molecular structure of title compound, with the atomic labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial packing diagram of title compound. Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x+2, -y, -z+2].
4-(4-Cyano-2-fluorophenoxy)phenyl 4-methylbenzenesulfonate top
Crystal data top
C20H14FNO4SZ = 2
Mr = 383.39F(000) = 396.00
Triclinic, P1Dx = 1.391 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 7.5504 (4) ÅCell parameters from 5883 reflections
b = 9.9558 (6) Åθ = 3.2–27.4°
c = 12.5862 (6) ŵ = 0.21 mm1
α = 89.5250 (15)°T = 296 K
β = 77.8080 (12)°Chunk, colorless
γ = 81.9370 (15)°0.42 × 0.32 × 0.28 mm
V = 915.40 (9) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2386 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.025
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.910, Tmax = 0.942k = 1212
9012 measured reflectionsl = 1616
4114 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0006Fo2 + 2σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.041(Δ/σ)max < 0.001
wR(F2) = 0.123Δρmax = 0.46 e Å3
S = 1.01Δρmin = 0.50 e Å3
4114 reflectionsExtinction correction: Larson (1970)
245 parametersExtinction coefficient: 591 (29)
H-atom parameters constrained
Crystal data top
C20H14FNO4Sγ = 81.9370 (15)°
Mr = 383.39V = 915.40 (9) Å3
Triclinic, P1Z = 2
a = 7.5504 (4) ÅMo Kα radiation
b = 9.9558 (6) ŵ = 0.21 mm1
c = 12.5862 (6) ÅT = 296 K
α = 89.5250 (15)°0.42 × 0.32 × 0.28 mm
β = 77.8080 (12)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4114 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2386 reflections with F2 > 2σ(F2)
Tmin = 0.910, Tmax = 0.942Rint = 0.025
9012 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041245 parameters
wR(F2) = 0.123H-atom parameters constrained
S = 1.01Δρmax = 0.46 e Å3
4114 reflectionsΔρmin = 0.50 e Å3
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.16109 (6)0.69907 (6)0.48722 (4)0.05510 (18)
F10.3393 (2)0.2172 (2)1.07043 (12)0.1276 (7)
O10.0493 (2)0.78677 (14)0.43051 (12)0.0702 (5)
O20.2714 (2)0.58197 (13)0.43277 (12)0.0653 (4)
O30.01598 (18)0.65207 (16)0.58710 (12)0.0606 (4)
O40.2671 (2)0.4109 (2)0.93536 (12)0.0767 (6)
N11.1212 (3)0.0868 (3)0.8909 (2)0.1196 (11)
C10.2945 (2)0.7893 (2)0.54964 (16)0.0488 (6)
C20.4542 (2)0.7240 (2)0.57449 (19)0.0607 (7)
C30.5538 (2)0.7947 (2)0.6284 (2)0.0670 (8)
C40.4972 (3)0.9299 (2)0.65809 (18)0.0635 (7)
C50.3378 (3)0.9927 (2)0.63241 (19)0.0680 (7)
C60.2358 (3)0.9238 (2)0.57855 (18)0.0604 (7)
C70.6053 (4)1.0073 (3)0.7184 (2)0.0936 (10)
C80.0820 (2)0.5862 (2)0.67430 (18)0.0522 (6)
C90.1745 (2)0.4561 (2)0.66080 (18)0.0554 (6)
C100.2391 (2)0.3966 (2)0.74779 (18)0.0613 (7)
C110.2089 (2)0.4676 (2)0.84456 (18)0.0614 (7)
C120.1107 (3)0.5944 (2)0.8574 (2)0.0739 (8)
C130.0470 (3)0.6553 (2)0.7708 (2)0.0704 (8)
C140.4443 (3)0.3479 (2)0.92161 (17)0.0645 (7)
C150.4799 (3)0.2471 (3)0.99270 (19)0.0762 (8)
C160.6506 (3)0.1772 (2)0.98788 (19)0.0780 (8)
C170.7936 (3)0.2105 (2)0.90833 (18)0.0687 (8)
C180.7627 (3)0.3131 (2)0.8374 (2)0.0742 (8)
C190.5882 (3)0.3820 (2)0.84441 (19)0.0716 (8)
C200.9752 (3)0.1401 (3)0.8989 (2)0.0856 (10)
H20.49400.63320.55500.073*
H30.66110.75070.64520.080*
H50.29801.08360.65180.082*
H60.12830.96770.56190.072*
H90.19320.40930.59490.066*
H100.30260.30900.74070.074*
H120.08670.63990.92430.089*
H130.01880.74210.77860.085*
H160.67030.10901.03680.094*
H180.85940.33600.78470.089*
H190.56810.45160.79680.086*
H710.56300.99860.79530.112*
H720.58891.10140.70010.112*
H730.73280.97110.69810.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0528 (3)0.0515 (3)0.0600 (3)0.0018 (2)0.0156 (2)0.0017 (2)
F10.0771 (10)0.191 (2)0.0934 (11)0.0040 (11)0.0113 (9)0.0689 (12)
O10.0738 (10)0.0636 (11)0.0790 (10)0.0040 (8)0.0384 (9)0.0084 (8)
O20.0729 (10)0.0498 (10)0.0666 (9)0.0062 (8)0.0093 (8)0.0106 (7)
O30.0409 (7)0.0681 (10)0.0715 (9)0.0008 (7)0.0141 (7)0.0079 (8)
O40.0641 (10)0.1006 (16)0.0548 (9)0.0083 (10)0.0018 (7)0.0114 (9)
N10.0747 (17)0.165 (2)0.1032 (19)0.0130 (18)0.0039 (14)0.0380 (19)
C10.0450 (11)0.0443 (13)0.0541 (11)0.0034 (9)0.0102 (9)0.0015 (9)
C20.0450 (12)0.0501 (14)0.0829 (15)0.0025 (11)0.0104 (11)0.0006 (12)
C30.0465 (12)0.0709 (18)0.0860 (17)0.0043 (12)0.0224 (12)0.0092 (14)
C40.0649 (15)0.0703 (18)0.0600 (13)0.0209 (13)0.0165 (11)0.0107 (12)
C50.0849 (17)0.0489 (15)0.0714 (15)0.0026 (13)0.0239 (13)0.0035 (12)
C60.0632 (14)0.0500 (15)0.0671 (14)0.0072 (12)0.0217 (11)0.0003 (11)
C70.104 (2)0.102 (2)0.0925 (19)0.0405 (19)0.0434 (17)0.0119 (17)
C80.0375 (10)0.0554 (14)0.0617 (13)0.0048 (10)0.0070 (9)0.0044 (11)
C90.0535 (12)0.0537 (14)0.0606 (13)0.0104 (11)0.0140 (10)0.0015 (11)
C100.0568 (13)0.0537 (15)0.0693 (15)0.0022 (11)0.0078 (11)0.0036 (12)
C110.0494 (13)0.0771 (18)0.0532 (13)0.0028 (12)0.0047 (10)0.0063 (12)
C120.0739 (16)0.082 (2)0.0560 (14)0.0051 (15)0.0019 (12)0.0138 (13)
C130.0649 (15)0.0649 (17)0.0692 (15)0.0126 (13)0.0006 (12)0.0062 (13)
C140.0558 (14)0.0872 (19)0.0487 (12)0.0056 (13)0.0100 (11)0.0058 (12)
C150.0596 (15)0.109 (2)0.0517 (13)0.0074 (15)0.0026 (12)0.0185 (14)
C160.0692 (16)0.100 (2)0.0597 (14)0.0042 (15)0.0077 (13)0.0218 (14)
C170.0581 (14)0.091 (2)0.0558 (13)0.0062 (13)0.0126 (11)0.0020 (13)
C180.0587 (15)0.106 (2)0.0598 (14)0.0209 (14)0.0108 (11)0.0124 (14)
C190.0630 (15)0.092 (2)0.0617 (14)0.0169 (14)0.0156 (12)0.0184 (13)
C200.0653 (17)0.119 (2)0.0667 (16)0.0003 (17)0.0093 (14)0.0178 (16)
Geometric parameters (Å, º) top
S1—O11.4220 (16)C14—C151.376 (3)
S1—O21.4221 (13)C14—C191.375 (3)
S1—O31.5975 (14)C15—C161.366 (3)
S1—C11.744 (2)C16—C171.384 (3)
F1—C151.348 (2)C17—C181.379 (3)
O3—C81.418 (2)C17—C201.431 (3)
O4—C111.397 (2)C18—C191.383 (3)
O4—C141.371 (2)C2—H20.930
N1—C201.139 (3)C3—H30.930
C1—C21.382 (2)C5—H50.930
C1—C61.377 (3)C6—H60.930
C2—C31.375 (3)C7—H710.960
C3—C41.384 (3)C7—H720.960
C4—C51.376 (3)C7—H730.960
C4—C71.511 (4)C9—H90.930
C5—C61.378 (3)C10—H100.930
C8—C91.376 (3)C12—H120.930
C8—C131.359 (3)C13—H130.930
C9—C101.386 (3)C16—H160.930
C10—C111.374 (3)C18—H180.930
C11—C121.363 (3)C19—H190.930
C12—C131.384 (3)
O1—S1—O2119.42 (9)C16—C17—C18120.1 (2)
O1—S1—O3102.89 (8)C16—C17—C20120.8 (2)
O1—S1—C1111.32 (10)C18—C17—C20119.1 (2)
O2—S1—O3108.85 (8)C17—C18—C19120.2 (2)
O2—S1—C1109.48 (9)C14—C19—C18120.2 (2)
O3—S1—C1103.47 (8)N1—C20—C17178.4 (3)
S1—O3—C8118.35 (12)C1—C2—H2120.3
C11—O4—C14118.07 (15)C3—C2—H2120.3
S1—C1—C2119.91 (17)C2—C3—H3119.4
S1—C1—C6119.74 (16)C4—C3—H3119.4
C2—C1—C6120.3 (2)C4—C5—H5119.3
C1—C2—C3119.4 (2)C6—C5—H5119.3
C2—C3—C4121.2 (2)C1—C6—H6120.3
C3—C4—C5118.3 (2)C5—C6—H6120.3
C3—C4—C7121.3 (2)C4—C7—H71109.5
C5—C4—C7120.4 (2)C4—C7—H72109.5
C4—C5—C6121.4 (2)C4—C7—H73109.5
C1—C6—C5119.4 (2)H71—C7—H72109.5
O3—C8—C9120.46 (19)H71—C7—H73109.5
O3—C8—C13117.51 (19)H72—C7—H73109.5
C9—C8—C13122.0 (2)C8—C9—H9120.8
C8—C9—C10118.4 (2)C10—C9—H9120.8
C9—C10—C11119.7 (2)C9—C10—H10120.1
O4—C11—C10121.9 (2)C11—C10—H10120.1
O4—C11—C12117.2 (2)C11—C12—H12120.1
C10—C11—C12120.8 (2)C13—C12—H12120.1
C11—C12—C13119.9 (2)C8—C13—H13120.5
C8—C13—C12119.0 (2)C12—C13—H13120.5
O4—C14—C15117.19 (19)C15—C16—H16120.9
O4—C14—C19124.5 (2)C17—C16—H16120.9
C15—C14—C19118.3 (2)C17—C18—H18119.9
F1—C15—C14118.0 (2)C19—C18—H18119.9
F1—C15—C16119.1 (2)C14—C19—H19119.9
C14—C15—C16122.9 (2)C18—C19—H19119.9
C15—C16—C17118.3 (2)
O1—S1—O3—C8166.73 (15)C4—C5—C6—C10.1 (2)
O1—S1—C1—C2156.85 (16)O3—C8—C9—C10178.99 (19)
O1—S1—C1—C626.20 (19)O3—C8—C13—C12179.5 (2)
O2—S1—O3—C865.64 (17)C9—C8—C13—C121.9 (3)
O2—S1—C1—C222.63 (19)C13—C8—C9—C102.4 (3)
O2—S1—C1—C6160.42 (16)C8—C9—C10—C110.3 (3)
O3—S1—C1—C293.29 (17)C9—C10—C11—O4178.3 (2)
O3—S1—C1—C683.66 (17)C9—C10—C11—C122.2 (3)
C1—S1—O3—C850.73 (17)O4—C11—C12—C13179.1 (2)
S1—O3—C8—C971.2 (2)C10—C11—C12—C132.8 (3)
S1—O3—C8—C13110.10 (19)C11—C12—C13—C80.8 (3)
C11—O4—C14—C15153.2 (2)O4—C14—C15—F10.0 (3)
C11—O4—C14—C1929.1 (3)O4—C14—C15—C16179.7 (2)
C14—O4—C11—C1048.8 (3)O4—C14—C19—C18179.5 (2)
C14—O4—C11—C12134.9 (2)C15—C14—C19—C181.8 (4)
S1—C1—C2—C3176.91 (16)C19—C14—C15—F1177.9 (2)
S1—C1—C6—C5176.99 (16)C19—C14—C15—C161.9 (4)
C2—C1—C6—C50.1 (2)F1—C15—C16—C17179.2 (2)
C6—C1—C2—C30.0 (2)C14—C15—C16—C170.5 (4)
C1—C2—C3—C40.1 (2)C15—C16—C17—C180.9 (4)
C2—C3—C4—C50.0 (2)C15—C16—C17—C20179.6 (2)
C2—C3—C4—C7179.3 (2)C16—C17—C18—C190.9 (4)
C3—C4—C5—C60.0 (2)C20—C17—C18—C19179.6 (2)
C7—C4—C5—C6179.3 (2)C17—C18—C19—C140.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N1i0.932.613.461 (3)152
Symmetry code: (i) x+2, y, z+2.

Experimental details

Crystal data
Chemical formulaC20H14FNO4S
Mr383.39
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.5504 (4), 9.9558 (6), 12.5862 (6)
α, β, γ (°)89.5250 (15), 77.8080 (12), 81.9370 (15)
V3)915.40 (9)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.42 × 0.32 × 0.28
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.910, 0.942
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
9012, 4114, 2386
Rint0.025
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.123, 1.01
No. of reflections4114
No. of parameters245
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.50

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), and Larson (1970), SHELXS97 (Sheldrick, 2008), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N1i0.93002.61003.461 (3)152.00
Symmetry code: (i) x+2, y, z+2.
 

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