2-Nitro-p-phenyl-ene bis-(toluene-sulfonate).

In the mol-ecule of the title compound, C(20)H(17)NO(8)S(2), 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 intra-molecular C-H⋯O hydrogen bond results in the formation of a five-membered ring, which adopts an envelope conformation. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules. 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 ▶); Hu et al. (2001 ▶); Svensson et al. (1998 ▶); Trollsås et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H17NO8S2

M = 463.49

Triclinic,

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 ▶) 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 ▶), 315 Friedel Pairs

Flack parameter: 0.21 (13)

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

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

C20H17NO8S2	Z = 1
Mr = 463.49	F000 = 240
Triclinic, P1	Dx = 1.424 Mg m−3
Hall symbol: P 1	Melting point: 415 K
a = 7.926 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.244 (3) Å	Cell parameters from 1246 reflections
c = 8.709 (3) Å	θ = 2.6–26.9º
α = 98.323 (6)º	µ = 0.29 mm−1
β = 96.180 (6)º	T = 294 (2) K
γ = 103.915 (6)º	Block, colorless
V = 540.5 (3) Å3	0.26 × 0.22 × 0.16 mm

Bruker SMART CCD area-detector diffractometer	1918 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
T = 294(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.928, Tmax = 0.955	k = −7→9
2693 measured reflections	l = −10→8

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-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 = 1.05	Δρmax = 0.38 e Å−3
1918 reflections	Δρmin = −0.29 e Å−3
282 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 315 Friedel Pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.21 (13)

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.

	x	y	z	Uiso*/Ueq
S1	0.2533 (2)	0.96499 (17)	1.25707 (16)	0.0455 (6)
S2	−0.0820 (2)	0.52158 (16)	0.40141 (16)	0.0461 (6)
O1	0.1899 (10)	1.0093 (7)	1.3993 (6)	0.0661 (19)
O2	0.3449 (8)	0.8397 (6)	1.2462 (6)	0.0602 (18)
O3	0.0766 (7)	0.8988 (6)	1.1351 (6)	0.0461 (14)
O4	0.0995 (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)
O7	0.2194 (9)	0.3656 (8)	0.7024 (7)	0.103 (2)
O8	0.0174 (10)	0.3014 (7)	0.8493 (7)	0.104 (2)
N1	0.1160 (10)	0.4007 (7)	0.7819 (7)	0.0713 (17)
C1	0.3630 (12)	1.1486 (10)	1.1911 (10)	0.043 (2)
C2	0.4931 (12)	1.1343 (12)	1.0940 (10)	0.058 (3)
H2	0.5251	1.0333	1.0693	0.069*
C3	0.5700 (14)	1.2794 (13)	1.0380 (11)	0.066 (3)
H3	0.6527	1.2728	0.9709	0.080*
C4	0.5312 (14)	1.4300 (14)	1.0756 (12)	0.063 (3)
C5	0.4075 (13)	1.4426 (12)	1.1802 (12)	0.068 (3)
H5	0.3828	1.5461	1.2115	0.082*
C6	0.3232 (12)	1.2979 (11)	1.2355 (10)	0.055 (3)
H6	0.2402	1.3040	1.3025	0.066*
C7	0.6108 (16)	1.5928 (14)	1.0174 (12)	0.100 (4)
H7A	0.7225	1.6490	1.0800	0.150*
H7B	0.5334	1.6661	1.0256	0.150*
H7C	0.6267	1.5659	0.9098	0.150*
C8	0.0860 (11)	0.8191 (9)	0.9787 (8)	0.039 (2)
C9	0.0942 (10)	0.6546 (8)	0.9560 (9)	0.0405 (19)
H9	0.0989	0.5959	1.0392	0.049*
C10	0.0717 (12)	0.9097 (10)	0.8580 (9)	0.049 (2)
H10	0.0579	1.0193	0.8773	0.058*
C11	0.0786 (11)	0.8330 (9)	0.7098 (9)	0.050 (2)
H11	0.0740	0.8936	0.6279	0.060*
C12	0.0926 (10)	0.6654 (10)	0.6776 (9)	0.040 (2)
C13	0.0952 (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	−0.3577	0.4514	0.5797	0.055*
C16	−0.4131 (12)	0.2048 (11)	0.6089 (10)	0.051 (2)
H16	−0.5036	0.2094	0.6679	0.061*
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	−0.0540	0.4571	0.071*
C19	−0.1494 (11)	0.1887 (10)	0.4286 (10)	0.053 (3)
H19	−0.0600	0.1833	0.3686	0.064*
C20	−0.4603 (13)	−0.1022 (13)	0.6365 (12)	0.082 (3)
H20A	−0.5067	−0.1946	0.5501	0.123*
H20B	−0.5548	−0.0775	0.6878	0.123*
H20C	−0.3792	−0.1331	0.7097	0.123*

	U11	U22	U33	U12	U13	U23
S1	0.0547 (15)	0.0356 (11)	0.0427 (13)	0.0047 (10)	0.0065 (11)	0.0075 (9)
S2	0.0554 (15)	0.0371 (12)	0.0423 (13)	0.0051 (10)	0.0035 (11)	0.0100 (9)
O1	0.097 (6)	0.056 (4)	0.043 (4)	0.009 (4)	0.017 (4)	0.012 (3)
O2	0.071 (5)	0.042 (4)	0.067 (4)	0.017 (3)	−0.001 (4)	0.016 (3)
O3	0.049 (4)	0.043 (3)	0.042 (3)	0.007 (3)	0.007 (3)	0.000 (2)
O4	0.046 (4)	0.048 (3)	0.044 (4)	0.000 (3)	0.011 (3)	0.008 (2)
O5	0.065 (5)	0.039 (4)	0.070 (4)	0.009 (3)	−0.004 (4)	0.009 (3)
O6	0.071 (5)	0.058 (4)	0.038 (4)	−0.002 (3)	0.014 (3)	0.013 (3)
O7	0.127 (5)	0.102 (5)	0.103 (4)	0.080 (4)	0.018 (4)	0.004 (3)
O8	0.169 (6)	0.043 (3)	0.103 (4)	0.029 (3)	0.009 (4)	0.031 (3)
N1	0.099 (5)	0.050 (3)	0.062 (3)	0.029 (3)	−0.016 (3)	0.003 (3)
C1	0.041 (6)	0.034 (5)	0.048 (6)	−0.001 (4)	0.003 (4)	0.006 (4)
C2	0.062 (7)	0.067 (6)	0.050 (5)	0.018 (5)	0.026 (5)	0.009 (4)
C3	0.063 (7)	0.075 (8)	0.055 (6)	0.000 (5)	0.017 (5)	0.016 (5)
C4	0.049 (7)	0.066 (7)	0.066 (7)	−0.004 (5)	−0.007 (5)	0.033 (5)
C5	0.054 (7)	0.043 (6)	0.106 (10)	0.006 (5)	0.005 (7)	0.024 (5)
C6	0.057 (7)	0.040 (5)	0.074 (7)	0.021 (5)	0.013 (5)	0.014 (4)
C7	0.085 (8)	0.093 (9)	0.099 (9)	−0.031 (7)	−0.006 (7)	0.048 (6)
C8	0.039 (5)	0.032 (4)	0.040 (5)	−0.002 (4)	0.006 (4)	0.008 (3)
C9	0.049 (6)	0.030 (4)	0.042 (5)	0.007 (4)	0.003 (4)	0.013 (3)
C10	0.060 (7)	0.028 (5)	0.050 (6)	0.005 (4)	−0.008 (5)	0.005 (4)
C11	0.056 (6)	0.041 (5)	0.046 (6)	−0.004 (4)	−0.003 (4)	0.020 (4)
C12	0.029 (5)	0.040 (5)	0.047 (6)	0.002 (4)	0.001 (4)	0.011 (4)
C13	0.041 (5)	0.033 (5)	0.050 (6)	0.008 (4)	0.006 (4)	0.013 (3)
C14	0.039 (5)	0.043 (5)	0.034 (5)	0.011 (4)	0.003 (4)	0.008 (4)
C15	0.040 (5)	0.036 (5)	0.056 (5)	0.006 (4)	−0.002 (4)	0.002 (3)
C16	0.040 (5)	0.070 (6)	0.047 (5)	0.014 (5)	0.012 (4)	0.018 (4)
C17	0.042 (6)	0.052 (6)	0.062 (6)	−0.004 (5)	0.004 (5)	0.018 (5)
C18	0.058 (7)	0.042 (5)	0.082 (7)	0.016 (5)	0.014 (6)	0.018 (5)
C19	0.048 (6)	0.043 (5)	0.067 (7)	0.004 (4)	0.025 (5)	0.008 (4)
C20	0.064 (7)	0.083 (8)	0.112 (9)	0.011 (6)	0.021 (6)	0.061 (6)

S1—O2	1.396 (6)	C7—H7B	0.9600
S1—O1	1.419 (6)	C7—H7C	0.9600
S1—O3	1.591 (6)	C8—C9	1.360 (9)
S1—C1	1.762 (8)	C8—C10	1.385 (10)
S2—O6	1.422 (5)	C9—C13	1.389 (9)
S2—O5	1.439 (6)	C9—H9	0.9300
S2—O4	1.643 (6)	C10—C11	1.366 (10)
S2—C14	1.752 (9)	C10—H10	0.9300
O3—C8	1.441 (8)	C11—C12	1.403 (10)
O4—C12	1.373 (8)	C11—H11	0.9300
O7—N1	1.189 (7)	C12—C13	1.398 (10)
O8—N1	1.247 (8)	C14—C15	1.355 (10)
N1—C13	1.494 (9)	C14—C19	1.405 (10)
C1—C6	1.357 (10)	C15—C16	1.400 (12)
C1—C2	1.417 (10)	C15—H15	0.9300
C2—C3	1.387 (13)	C16—C17	1.380 (12)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.353 (13)	C17—C18	1.374 (11)
C3—H3	0.9300	C17—C20	1.532 (12)
C4—C5	1.419 (13)	C18—C19	1.374 (12)
C4—C7	1.521 (14)	C18—H18	0.9300
C5—C6	1.399 (13)	C19—H19	0.9300
C5—H5	0.9300	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—H7A	0.9600	C20—H20C	0.9600
O2—S1—O1	119.0 (4)	C9—C8—O3	118.2 (6)
O2—S1—O3	108.4 (3)	C10—C8—O3	118.1 (7)
O1—S1—O3	102.0 (4)	C8—C9—C13	117.3 (7)
O2—S1—C1	112.4 (4)	C8—C9—H9	121.3
O1—S1—C1	110.6 (4)	C13—C9—H9	121.3
O3—S1—C1	102.5 (4)	C11—C10—C8	117.9 (8)
O6—S2—O5	122.6 (4)	C11—C10—H10	121.0
O6—S2—O4	102.9 (3)	C8—C10—H10	121.0
O5—S2—O4	108.1 (3)	C10—C11—C12	121.8 (7)
O6—S2—C14	110.0 (4)	C10—C11—H11	119.1
O5—S2—C14	108.1 (4)	C12—C11—H11	119.1
O4—S2—C14	103.4 (4)	O4—C12—C13	120.7 (7)
C8—O3—S1	118.2 (5)	O4—C12—C11	122.0 (7)
C12—O4—S2	119.0 (5)	C13—C12—C11	117.3 (7)
O7—N1—O8	125.9 (6)	C9—C13—C12	121.9 (7)
O7—N1—C13	119.0 (7)	C9—C13—N1	116.6 (6)
O8—N1—C13	115.1 (6)	C12—C13—N1	121.2 (7)
C6—C1—C2	122.3 (9)	C15—C14—C19	120.7 (8)
C6—C1—S1	119.7 (7)	C15—C14—S2	120.8 (6)
C2—C1—S1	118.0 (6)	C19—C14—S2	118.4 (7)
C3—C2—C1	116.2 (8)	C14—C15—C16	119.5 (8)
C3—C2—H2	121.9	C14—C15—H15	120.3
C1—C2—H2	121.9	C16—C15—H15	120.3
C4—C3—C2	123.6 (10)	C17—C16—C15	120.4 (8)
C4—C3—H3	118.2	C17—C16—H16	119.8
C2—C3—H3	118.2	C15—C16—H16	119.8
C3—C4—C5	118.8 (10)	C18—C17—C16	119.2 (9)
C3—C4—C7	125.8 (12)	C18—C17—C20	121.1 (9)
C5—C4—C7	115.3 (11)	C16—C17—C20	119.7 (9)
C6—C5—C4	119.3 (9)	C17—C18—C19	121.4 (9)
C6—C5—H5	120.3	C17—C18—H18	119.3
C4—C5—H5	120.3	C19—C18—H18	119.3
C1—C6—C5	119.6 (9)	C18—C19—C14	118.7 (8)
C1—C6—H6	120.2	C18—C19—H19	120.6
C5—C6—H6	120.2	C14—C19—H19	120.6
C4—C7—H7A	109.5	C17—C20—H20A	109.5
C4—C7—H7B	109.5	C17—C20—H20B	109.5
H7A—C7—H7B	109.5	H20A—C20—H20B	109.5
C4—C7—H7C	109.5	C17—C20—H20C	109.5
H7A—C7—H7C	109.5	H20A—C20—H20C	109.5
H7B—C7—H7C	109.5	H20B—C20—H20C	109.5
C9—C8—C10	123.5 (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—O4	179.9 (7)
C1—S1—O3—C8	74.1 (5)	C10—C11—C12—C13	1.4 (12)
O6—S2—O4—C12	171.7 (5)	C8—C9—C13—C12	1.6 (10)
O5—S2—O4—C12	40.7 (6)	C8—C9—C13—N1	176.1 (8)
C14—S2—O4—C12	−73.8 (6)	O4—C12—C13—C9	177.9 (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—N1	3.6 (12)
O3—S1—C1—C6	83.5 (7)	C11—C12—C13—N1	−177.8 (7)
O2—S1—C1—C2	18.8 (9)	O7—N1—C13—C9	−132.7 (7)
O1—S1—C1—C2	154.4 (8)	O8—N1—C13—C9	48.5 (9)
O3—S1—C1—C2	−97.4 (8)	O7—N1—C13—C12	41.8 (11)
C6—C1—C2—C3	−4.1 (15)	O8—N1—C13—C12	−136.9 (8)
S1—C1—C2—C3	176.8 (7)	O6—S2—C14—C15	−152.6 (7)
C1—C2—C3—C4	2.3 (16)	O5—S2—C14—C15	−16.4 (9)
C2—C3—C4—C5	1.1 (17)	O4—S2—C14—C15	98.0 (8)
C2—C3—C4—C7	−179.8 (9)	O6—S2—C14—C19	30.7 (8)
C3—C4—C5—C6	−3.0 (16)	O5—S2—C14—C19	166.9 (6)
C7—C4—C5—C6	177.8 (8)	O4—S2—C14—C19	−78.6 (6)
C2—C1—C6—C5	2.4 (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—C1	1.2 (14)	C14—C15—C16—C17	1.8 (13)
S1—O3—C8—C9	79.1 (8)	C15—C16—C17—C18	−2.6 (14)
S1—O3—C8—C10	−106.1 (8)	C15—C16—C17—C20	179.8 (9)
C10—C8—C9—C13	2.7 (12)	C16—C17—C18—C19	2.6 (15)
O3—C8—C9—C13	177.2 (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—C18	1.0 (12)
C8—C10—C11—C12	2.5 (12)	S2—C14—C19—C18	177.6 (7)
S2—O4—C12—C13	102.9 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.49	3.405 (11)	168
C9—H9···O6ii	0.93	2.46	3.319 (9)	153
C10—H10···O8i	0.93	2.47	3.369 (10)	164
C11—H11···O1iii	0.93	2.50	3.352 (10)	153
C15—H15···O5	0.93	2.56	2.923 (10)	104
C18—H18···O5iv	0.93	2.49	3.409 (11)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.49	3.405 (11)	168
C9—H9⋯O6ii	0.93	2.46	3.319 (9)	153
C10—H10⋯O8i	0.93	2.47	3.369 (10)	164
C11—H11⋯O1iii	0.93	2.50	3.352 (10)	153
C15—H15⋯O5	0.93	2.56	2.923 (10)	104
C18—H18⋯O5iv	0.93	2.49	3.409 (11)	168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .