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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1816.
Published online 2008 August 23. doi:  10.1107/S1600536808026573
PMCID: PMC2960664

2-Nitro-p-phenyl­ene bis­(toluene­sulfonate)

Abstract

In the mol­ecule of the title compound, C20H17NO8S2, the two toluene rings are oriented at a dihedral angle of 3.65 (4)°, while the nitrophenyl ring is oriented at dihedral angles of 44.39 (3) and 47.44 (3)° with respect to the toluene rings. An intra­molecular C—H(...)O hydrogen bond results in the formation of a five-membered ring, which adopts an envelope conformation. In the crystal structure, inter­molecular C—H(...)O hydrogen bonds link the mol­ecules. There is a π–π contact between the toluene rings [centroid–centroid distance = 4.035 (1) Å].

Related literature

For related literature, see: Atkinson et al. (2005 [triangle]); Hu et al. (2001 [triangle]); Svensson et al. (1998 [triangle]); Trollsås et al. (1996 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1816-scheme1.jpg

Experimental

Crystal data

  • C20H17NO8S2
  • M r = 463.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1816-efi1.jpg
  • a = 7.926 (3) Å
  • b = 8.244 (3) Å
  • c = 8.709 (3) Å
  • α = 98.323 (6)°
  • β = 96.180 (6)°
  • γ = 103.915 (6)°
  • V = 540.5 (3) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 294 (2) K
  • 0.26 × 0.22 × 0.16 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.928, T max = 0.955
  • 2693 measured reflections
  • 1918 independent reflections
  • 1717 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.135
  • S = 1.05
  • 1918 reflections
  • 282 parameters
  • H-atom parameters constrained
  • Δρmax = 0.38 e Å−3
  • Δρmin = −0.29 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 315 Friedel Pairs
  • Flack parameter: 0.21 (13)

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]) and PLATON (Spek, 2003 [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/S1600536808026573/hk2500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026573/hk2500Isup2.hkl

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

supplementary crystallographic information

Comment

Phenolic esters are useful intermediates in organic synthesis (Trollsås et al., 1996; Svensson et al., 1998; Atkinson et al., 2005; Hu et al., 2001). We have developed a new method for the syntheses of some phenolic esters. The title compound has been produced as a byproduct. We report herein its crystal structure.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1—C6), B (C8—C13) and C (C14—C19) are, of course, planar, and the dihedral angles between them are A/B = 44.39 (3)°, A/C = 3.65 (4)° and B/C = 47.44 (3)°. The intramolecular C—H···O hydrogen bond (Table 1) results in the formation of a five-membered ring D (S2/O5/C14/C15/H15), adopting envelope conformation, with O5 atom displaced by 0.356 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. A π—π contact between A and C rings Cg1···Cg3i [symmetry code: (i) 1 + x, 1 + y, 1 + z, where Cg1 and Cg3 are the centroids of the rings A and C, respectively] further stabilize the structure, with centroid-centroid distance of 4.035 (1) Å.

Experimental

For the preparation of the title compound, 2-nitrohydroquinone (155 mg, 1.0 mmol) was dissolved in chloroform (30 ml). To this solution, 4-toluenesulfonyl chloride (191 mg, 1.0 mmol) and triethylamine (101 mg, 1.0 mmol) were added, the reaction was stirred at room temperature for 3 h. The reaction mixture was extracted with dichloromethane and dried with anhydrous sodium sulfate. After concentration, the residue was separated by flash column chromatography and purified by recrystallization from chloroform (yield; 72 mg, 31%, m.p. 415 K). Spectroscopic analysis: IR (KBr, ν, cm-1): 3089, 2922, 1596, 1539, 1390, 1201, 1183, 1089. Analysis required for C20H17NO8S2: C 51.83; H 3.70; N 3.02%. Found: C 50.85; H 3.65; N 3.19%.

Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C20H17NO8S2Z = 1
Mr = 463.49F000 = 240
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: P 1Melting point: 415 K
a = 7.926 (3) ÅMo Kα radiation λ = 0.71073 Å
b = 8.244 (3) ÅCell parameters from 1246 reflections
c = 8.709 (3) Åθ = 2.6–26.9º
α = 98.323 (6)ºµ = 0.29 mm1
β = 96.180 (6)ºT = 294 (2) K
γ = 103.915 (6)ºBlock, colorless
V = 540.5 (3) Å30.26 × 0.22 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer1918 independent reflections
Radiation source: fine-focus sealed tube1717 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→6
Tmin = 0.928, Tmax = 0.955k = −7→9
2693 measured reflectionsl = −10→8

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045  w = 1/[σ2(Fo2) + (0.0884P)2 + 0.0596P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135(Δ/σ)max = 0.007
S = 1.05Δρmax = 0.38 e Å3
1918 reflectionsΔρmin = −0.29 e Å3
282 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 315 Friedel Pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.21 (13)

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
S10.2533 (2)0.96499 (17)1.25707 (16)0.0455 (6)
S2−0.0820 (2)0.52158 (16)0.40141 (16)0.0461 (6)
O10.1899 (10)1.0093 (7)1.3993 (6)0.0661 (19)
O20.3449 (8)0.8397 (6)1.2462 (6)0.0602 (18)
O30.0766 (7)0.8988 (6)1.1351 (6)0.0461 (14)
O40.0995 (7)0.5877 (7)0.5288 (6)0.0477 (15)
O5−0.1792 (8)0.6481 (6)0.4198 (6)0.0602 (17)
O6−0.0204 (8)0.4733 (7)0.2588 (6)0.0578 (16)
O70.2194 (9)0.3656 (8)0.7024 (7)0.103 (2)
O80.0174 (10)0.3014 (7)0.8493 (7)0.104 (2)
N10.1160 (10)0.4007 (7)0.7819 (7)0.0713 (17)
C10.3630 (12)1.1486 (10)1.1911 (10)0.043 (2)
C20.4931 (12)1.1343 (12)1.0940 (10)0.058 (3)
H20.52511.03331.06930.069*
C30.5700 (14)1.2794 (13)1.0380 (11)0.066 (3)
H30.65271.27280.97090.080*
C40.5312 (14)1.4300 (14)1.0756 (12)0.063 (3)
C50.4075 (13)1.4426 (12)1.1802 (12)0.068 (3)
H50.38281.54611.21150.082*
C60.3232 (12)1.2979 (11)1.2355 (10)0.055 (3)
H60.24021.30401.30250.066*
C70.6108 (16)1.5928 (14)1.0174 (12)0.100 (4)
H7A0.72251.64901.08000.150*
H7B0.53341.66611.02560.150*
H7C0.62671.56590.90980.150*
C80.0860 (11)0.8191 (9)0.9787 (8)0.039 (2)
C90.0942 (10)0.6546 (8)0.9560 (9)0.0405 (19)
H90.09890.59591.03920.049*
C100.0717 (12)0.9097 (10)0.8580 (9)0.049 (2)
H100.05791.01930.87730.058*
C110.0786 (11)0.8330 (9)0.7098 (9)0.050 (2)
H110.07400.89360.62790.060*
C120.0926 (10)0.6654 (10)0.6776 (9)0.040 (2)
C130.0952 (10)0.5776 (9)0.8033 (9)0.041 (2)
C14−0.1986 (12)0.3410 (11)0.4653 (9)0.039 (2)
C15−0.3270 (10)0.3498 (10)0.5546 (9)0.046 (2)
H15−0.35770.45140.57970.055*
C16−0.4131 (12)0.2048 (11)0.6089 (10)0.051 (2)
H16−0.50360.20940.66790.061*
C17−0.3648 (13)0.0550 (12)0.5756 (10)0.054 (3)
C18−0.2358 (13)0.0481 (11)0.4832 (11)0.059 (3)
H18−0.2063−0.05400.45710.071*
C19−0.1494 (11)0.1887 (10)0.4286 (10)0.053 (3)
H19−0.06000.18330.36860.064*
C20−0.4603 (13)−0.1022 (13)0.6365 (12)0.082 (3)
H20A−0.5067−0.19460.55010.123*
H20B−0.5548−0.07750.68780.123*
H20C−0.3792−0.13310.70970.123*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0547 (15)0.0356 (11)0.0427 (13)0.0047 (10)0.0065 (11)0.0075 (9)
S20.0554 (15)0.0371 (12)0.0423 (13)0.0051 (10)0.0035 (11)0.0100 (9)
O10.097 (6)0.056 (4)0.043 (4)0.009 (4)0.017 (4)0.012 (3)
O20.071 (5)0.042 (4)0.067 (4)0.017 (3)−0.001 (4)0.016 (3)
O30.049 (4)0.043 (3)0.042 (3)0.007 (3)0.007 (3)0.000 (2)
O40.046 (4)0.048 (3)0.044 (4)0.000 (3)0.011 (3)0.008 (2)
O50.065 (5)0.039 (4)0.070 (4)0.009 (3)−0.004 (4)0.009 (3)
O60.071 (5)0.058 (4)0.038 (4)−0.002 (3)0.014 (3)0.013 (3)
O70.127 (5)0.102 (5)0.103 (4)0.080 (4)0.018 (4)0.004 (3)
O80.169 (6)0.043 (3)0.103 (4)0.029 (3)0.009 (4)0.031 (3)
N10.099 (5)0.050 (3)0.062 (3)0.029 (3)−0.016 (3)0.003 (3)
C10.041 (6)0.034 (5)0.048 (6)−0.001 (4)0.003 (4)0.006 (4)
C20.062 (7)0.067 (6)0.050 (5)0.018 (5)0.026 (5)0.009 (4)
C30.063 (7)0.075 (8)0.055 (6)0.000 (5)0.017 (5)0.016 (5)
C40.049 (7)0.066 (7)0.066 (7)−0.004 (5)−0.007 (5)0.033 (5)
C50.054 (7)0.043 (6)0.106 (10)0.006 (5)0.005 (7)0.024 (5)
C60.057 (7)0.040 (5)0.074 (7)0.021 (5)0.013 (5)0.014 (4)
C70.085 (8)0.093 (9)0.099 (9)−0.031 (7)−0.006 (7)0.048 (6)
C80.039 (5)0.032 (4)0.040 (5)−0.002 (4)0.006 (4)0.008 (3)
C90.049 (6)0.030 (4)0.042 (5)0.007 (4)0.003 (4)0.013 (3)
C100.060 (7)0.028 (5)0.050 (6)0.005 (4)−0.008 (5)0.005 (4)
C110.056 (6)0.041 (5)0.046 (6)−0.004 (4)−0.003 (4)0.020 (4)
C120.029 (5)0.040 (5)0.047 (6)0.002 (4)0.001 (4)0.011 (4)
C130.041 (5)0.033 (5)0.050 (6)0.008 (4)0.006 (4)0.013 (3)
C140.039 (5)0.043 (5)0.034 (5)0.011 (4)0.003 (4)0.008 (4)
C150.040 (5)0.036 (5)0.056 (5)0.006 (4)−0.002 (4)0.002 (3)
C160.040 (5)0.070 (6)0.047 (5)0.014 (5)0.012 (4)0.018 (4)
C170.042 (6)0.052 (6)0.062 (6)−0.004 (5)0.004 (5)0.018 (5)
C180.058 (7)0.042 (5)0.082 (7)0.016 (5)0.014 (6)0.018 (5)
C190.048 (6)0.043 (5)0.067 (7)0.004 (4)0.025 (5)0.008 (4)
C200.064 (7)0.083 (8)0.112 (9)0.011 (6)0.021 (6)0.061 (6)

Geometric parameters (Å, °)

S1—O21.396 (6)C7—H7B0.9600
S1—O11.419 (6)C7—H7C0.9600
S1—O31.591 (6)C8—C91.360 (9)
S1—C11.762 (8)C8—C101.385 (10)
S2—O61.422 (5)C9—C131.389 (9)
S2—O51.439 (6)C9—H90.9300
S2—O41.643 (6)C10—C111.366 (10)
S2—C141.752 (9)C10—H100.9300
O3—C81.441 (8)C11—C121.403 (10)
O4—C121.373 (8)C11—H110.9300
O7—N11.189 (7)C12—C131.398 (10)
O8—N11.247 (8)C14—C151.355 (10)
N1—C131.494 (9)C14—C191.405 (10)
C1—C61.357 (10)C15—C161.400 (12)
C1—C21.417 (10)C15—H150.9300
C2—C31.387 (13)C16—C171.380 (12)
C2—H20.9300C16—H160.9300
C3—C41.353 (13)C17—C181.374 (11)
C3—H30.9300C17—C201.532 (12)
C4—C51.419 (13)C18—C191.374 (12)
C4—C71.521 (14)C18—H180.9300
C5—C61.399 (13)C19—H190.9300
C5—H50.9300C20—H20A0.9600
C6—H60.9300C20—H20B0.9600
C7—H7A0.9600C20—H20C0.9600
O2—S1—O1119.0 (4)C9—C8—O3118.2 (6)
O2—S1—O3108.4 (3)C10—C8—O3118.1 (7)
O1—S1—O3102.0 (4)C8—C9—C13117.3 (7)
O2—S1—C1112.4 (4)C8—C9—H9121.3
O1—S1—C1110.6 (4)C13—C9—H9121.3
O3—S1—C1102.5 (4)C11—C10—C8117.9 (8)
O6—S2—O5122.6 (4)C11—C10—H10121.0
O6—S2—O4102.9 (3)C8—C10—H10121.0
O5—S2—O4108.1 (3)C10—C11—C12121.8 (7)
O6—S2—C14110.0 (4)C10—C11—H11119.1
O5—S2—C14108.1 (4)C12—C11—H11119.1
O4—S2—C14103.4 (4)O4—C12—C13120.7 (7)
C8—O3—S1118.2 (5)O4—C12—C11122.0 (7)
C12—O4—S2119.0 (5)C13—C12—C11117.3 (7)
O7—N1—O8125.9 (6)C9—C13—C12121.9 (7)
O7—N1—C13119.0 (7)C9—C13—N1116.6 (6)
O8—N1—C13115.1 (6)C12—C13—N1121.2 (7)
C6—C1—C2122.3 (9)C15—C14—C19120.7 (8)
C6—C1—S1119.7 (7)C15—C14—S2120.8 (6)
C2—C1—S1118.0 (6)C19—C14—S2118.4 (7)
C3—C2—C1116.2 (8)C14—C15—C16119.5 (8)
C3—C2—H2121.9C14—C15—H15120.3
C1—C2—H2121.9C16—C15—H15120.3
C4—C3—C2123.6 (10)C17—C16—C15120.4 (8)
C4—C3—H3118.2C17—C16—H16119.8
C2—C3—H3118.2C15—C16—H16119.8
C3—C4—C5118.8 (10)C18—C17—C16119.2 (9)
C3—C4—C7125.8 (12)C18—C17—C20121.1 (9)
C5—C4—C7115.3 (11)C16—C17—C20119.7 (9)
C6—C5—C4119.3 (9)C17—C18—C19121.4 (9)
C6—C5—H5120.3C17—C18—H18119.3
C4—C5—H5120.3C19—C18—H18119.3
C1—C6—C5119.6 (9)C18—C19—C14118.7 (8)
C1—C6—H6120.2C18—C19—H19120.6
C5—C6—H6120.2C14—C19—H19120.6
C4—C7—H7A109.5C17—C20—H20A109.5
C4—C7—H7B109.5C17—C20—H20B109.5
H7A—C7—H7B109.5H20A—C20—H20B109.5
C4—C7—H7C109.5C17—C20—H20C109.5
H7A—C7—H7C109.5H20A—C20—H20C109.5
H7B—C7—H7C109.5H20B—C20—H20C109.5
C9—C8—C10123.5 (7)
O2—S1—O3—C8−45.0 (6)S2—O4—C12—C11−75.6 (9)
O1—S1—O3—C8−171.4 (5)C10—C11—C12—O4179.9 (7)
C1—S1—O3—C874.1 (5)C10—C11—C12—C131.4 (12)
O6—S2—O4—C12171.7 (5)C8—C9—C13—C121.6 (10)
O5—S2—O4—C1240.7 (6)C8—C9—C13—N1176.1 (8)
C14—S2—O4—C12−73.8 (6)O4—C12—C13—C9177.9 (6)
O2—S1—C1—C6−160.2 (7)C11—C12—C13—C9−3.6 (11)
O1—S1—C1—C6−24.6 (9)O4—C12—C13—N13.6 (12)
O3—S1—C1—C683.5 (7)C11—C12—C13—N1−177.8 (7)
O2—S1—C1—C218.8 (9)O7—N1—C13—C9−132.7 (7)
O1—S1—C1—C2154.4 (8)O8—N1—C13—C948.5 (9)
O3—S1—C1—C2−97.4 (8)O7—N1—C13—C1241.8 (11)
C6—C1—C2—C3−4.1 (15)O8—N1—C13—C12−136.9 (8)
S1—C1—C2—C3176.8 (7)O6—S2—C14—C15−152.6 (7)
C1—C2—C3—C42.3 (16)O5—S2—C14—C15−16.4 (9)
C2—C3—C4—C51.1 (17)O4—S2—C14—C1598.0 (8)
C2—C3—C4—C7−179.8 (9)O6—S2—C14—C1930.7 (8)
C3—C4—C5—C6−3.0 (16)O5—S2—C14—C19166.9 (6)
C7—C4—C5—C6177.8 (8)O4—S2—C14—C19−78.6 (6)
C2—C1—C6—C52.4 (14)C19—C14—C15—C16−0.9 (13)
S1—C1—C6—C5−178.6 (8)S2—C14—C15—C16−177.5 (6)
C4—C5—C6—C11.2 (14)C14—C15—C16—C171.8 (13)
S1—O3—C8—C979.1 (8)C15—C16—C17—C18−2.6 (14)
S1—O3—C8—C10−106.1 (8)C15—C16—C17—C20179.8 (9)
C10—C8—C9—C132.7 (12)C16—C17—C18—C192.6 (15)
O3—C8—C9—C13177.2 (7)C20—C17—C18—C19−179.8 (8)
C9—C8—C10—C11−4.7 (13)C17—C18—C19—C14−1.8 (14)
O3—C8—C10—C11−179.3 (7)C15—C14—C19—C181.0 (12)
C8—C10—C11—C122.5 (12)S2—C14—C19—C18177.6 (7)
S2—O4—C12—C13102.9 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O2i0.932.493.405 (11)168
C9—H9···O6ii0.932.463.319 (9)153
C10—H10···O8i0.932.473.369 (10)164
C11—H11···O1iii0.932.503.352 (10)153
C15—H15···O50.932.562.923 (10)104
C18—H18···O5iv0.932.493.409 (11)168

Symmetry codes: (i) x, y+1, z; (ii) x, y, z+1; (iii) x, y, z−1; (iv) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2500).

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