2-Nitro-p-phenyl-ene dibenzene-sulfonate.

In the title compound, C(18)H(13)NO(8)S(2), the nitro-phenyl ring forms dihedral angles of 46.67 (7) and 75.40 (6)° with the phenyl rings. The nitro group makes a dihedral angle of 26.13 (8)° with the attached ring. The crystal packing is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the use of phenolic esters in organic synthesis, see: Trollsås et al. (1996 ▶); Svensson et al. (1998 ▶); Atkinson et al. (2005 ▶); Hu et al. (2001 ▶). For a related structure, see: Ji et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H13NO8S2

M = 435.43

Monoclinic,

a = 11.669 (5) Å

b = 10.554 (4) Å

c = 15.343 (7) Å

β = 101.462 (7)°

V = 1851.9 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 113 K

0.30 × 0.07 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T min = 0.906, T max = 0.980

15174 measured reflections

4386 independent reflections

3278 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.121

S = 1.08

4386 reflections

262 parameters

H-atom parameters constrained

Δρmax = 1.11 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002898/bq2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002898/bq2192Isup2.hkl

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

C18H13NO8S2	F(000) = 896
Mr = 435.43	Dx = 1.562 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6872 reflections
a = 11.669 (5) Å	θ = 1.4–27.9°
b = 10.554 (4) Å	µ = 0.34 mm−1
c = 15.343 (7) Å	T = 113 K
β = 101.462 (7)°	Prism, colorless
V = 1851.9 (14) Å3	0.30 × 0.07 × 0.06 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	4386 independent reflections
Radiation source: Rotating anode	3278 reflections with I > 2σ(I)
multilayer	Rint = 0.035
Detector resolution: 14.63 pixels mm-1	θmax = 27.8°, θmin = 1.8°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	k = −12→13
Tmin = 0.906, Tmax = 0.980	l = −20→14
15174 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0646P)2] where P = (Fo2 + 2Fc2)/3
4386 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 1.11 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.47624 (5)	0.78506 (4)	0.24585 (3)	0.02226 (14)
S2	1.02988 (5)	0.38180 (5)	0.34494 (3)	0.02633 (15)
O1	0.46295 (13)	0.67436 (12)	0.19112 (9)	0.0252 (3)
O2	0.43170 (13)	0.90467 (13)	0.21175 (10)	0.0290 (4)
O3	0.61466 (13)	0.81300 (12)	0.27823 (10)	0.0248 (3)
O4	0.67578 (15)	0.81516 (13)	0.11784 (10)	0.0337 (4)
O5	0.69050 (14)	0.62624 (13)	0.06595 (9)	0.0302 (4)
O6	0.88958 (13)	0.37990 (13)	0.32927 (10)	0.0271 (3)
O7	1.06055 (15)	0.25648 (14)	0.37645 (10)	0.0369 (4)
O8	1.07180 (14)	0.49022 (15)	0.39729 (10)	0.0346 (4)
N1	0.69459 (15)	0.70129 (15)	0.12753 (11)	0.0233 (4)
C1	0.42957 (18)	0.75292 (18)	0.34514 (13)	0.0224 (4)
C2	0.4055 (2)	0.62808 (19)	0.36603 (14)	0.0281 (5)
H2	0.4156	0.5599	0.3278	0.034*
C3	0.3661 (2)	0.6070 (2)	0.44472 (15)	0.0341 (6)
H3	0.3498	0.5230	0.4610	0.041*
C4	0.3503 (2)	0.7068 (2)	0.49945 (15)	0.0334 (5)
H4	0.3208	0.6913	0.5519	0.040*
C5	0.3772 (2)	0.8296 (2)	0.47808 (15)	0.0336 (6)
H5	0.3686	0.8973	0.5171	0.040*
C6	0.4165 (2)	0.85408 (19)	0.40072 (14)	0.0274 (5)
H6	0.4343	0.9381	0.3856	0.033*
C7	0.68888 (17)	0.70745 (17)	0.28997 (13)	0.0212 (4)
C8	0.72464 (18)	0.66007 (18)	0.37471 (14)	0.0236 (4)
H8	0.7001	0.6999	0.4235	0.028*
C9	0.79652 (18)	0.55410 (19)	0.38883 (14)	0.0242 (4)
H9	0.8229	0.5218	0.4472	0.029*
C10	0.82902 (17)	0.49626 (18)	0.31632 (13)	0.0218 (4)
C11	0.79618 (17)	0.54331 (17)	0.23077 (13)	0.0212 (4)
H11	0.8203	0.5032	0.1820	0.025*
C12	0.72676 (17)	0.65101 (17)	0.21879 (13)	0.0199 (4)
C13	1.05739 (19)	0.40052 (19)	0.23713 (13)	0.0255 (5)
C14	1.1317 (2)	0.4954 (2)	0.22087 (16)	0.0348 (5)
H14	1.1657	0.5524	0.2667	0.042*
C15	1.1561 (2)	0.5059 (2)	0.13575 (18)	0.0460 (7)
H15	1.2078	0.5700	0.1233	0.055*
C16	1.1054 (3)	0.4237 (3)	0.06989 (16)	0.0470 (7)
H16	1.1222	0.4314	0.0120	0.056*
C17	1.0300 (3)	0.3298 (3)	0.08698 (16)	0.0451 (7)
H17	0.9949	0.2740	0.0407	0.054*
C18	1.0057 (2)	0.3169 (2)	0.17063 (16)	0.0352 (6)
H18	0.9547	0.2521	0.1828	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0194 (3)	0.0219 (3)	0.0260 (3)	0.00342 (19)	0.0056 (2)	0.0013 (2)
S2	0.0199 (3)	0.0352 (3)	0.0239 (3)	0.0062 (2)	0.0046 (2)	0.0068 (2)
O1	0.0246 (8)	0.0264 (7)	0.0247 (7)	0.0009 (6)	0.0049 (6)	−0.0019 (6)
O2	0.0293 (9)	0.0253 (7)	0.0337 (8)	0.0094 (6)	0.0097 (7)	0.0064 (6)
O3	0.0191 (8)	0.0197 (7)	0.0358 (8)	0.0021 (5)	0.0063 (6)	−0.0014 (6)
O4	0.0399 (10)	0.0241 (8)	0.0382 (9)	0.0079 (7)	0.0102 (8)	0.0108 (7)
O5	0.0348 (9)	0.0310 (8)	0.0246 (8)	−0.0030 (7)	0.0055 (7)	0.0013 (7)
O6	0.0192 (8)	0.0278 (7)	0.0350 (8)	0.0049 (6)	0.0069 (7)	0.0087 (6)
O7	0.0337 (10)	0.0424 (9)	0.0373 (9)	0.0174 (7)	0.0132 (8)	0.0187 (8)
O8	0.0247 (9)	0.0511 (9)	0.0268 (8)	0.0040 (7)	0.0023 (7)	−0.0051 (7)
N1	0.0200 (9)	0.0249 (9)	0.0261 (9)	0.0002 (7)	0.0071 (7)	0.0038 (7)
C1	0.0191 (10)	0.0236 (10)	0.0241 (10)	0.0014 (8)	0.0032 (8)	−0.0007 (8)
C2	0.0318 (13)	0.0228 (10)	0.0309 (11)	−0.0029 (9)	0.0093 (10)	−0.0063 (9)
C3	0.0443 (15)	0.0274 (11)	0.0326 (12)	−0.0097 (10)	0.0125 (11)	−0.0016 (9)
C4	0.0452 (15)	0.0326 (12)	0.0237 (11)	−0.0062 (10)	0.0100 (10)	−0.0024 (9)
C5	0.0461 (16)	0.0278 (11)	0.0274 (11)	0.0003 (10)	0.0090 (11)	−0.0064 (9)
C6	0.0328 (13)	0.0203 (10)	0.0287 (11)	0.0022 (8)	0.0053 (10)	−0.0005 (8)
C7	0.0156 (10)	0.0193 (9)	0.0284 (10)	−0.0013 (7)	0.0038 (8)	−0.0018 (8)
C8	0.0180 (10)	0.0277 (10)	0.0262 (10)	−0.0040 (8)	0.0069 (8)	−0.0051 (9)
C9	0.0193 (10)	0.0292 (10)	0.0230 (10)	−0.0031 (8)	0.0017 (8)	0.0026 (9)
C10	0.0155 (10)	0.0227 (9)	0.0272 (10)	0.0012 (8)	0.0046 (8)	0.0042 (8)
C11	0.0179 (10)	0.0234 (10)	0.0237 (10)	−0.0007 (8)	0.0074 (8)	0.0001 (8)
C12	0.0165 (10)	0.0201 (9)	0.0230 (10)	−0.0014 (7)	0.0040 (8)	0.0030 (8)
C13	0.0232 (11)	0.0318 (11)	0.0223 (10)	0.0102 (9)	0.0061 (8)	0.0052 (9)
C14	0.0304 (13)	0.0365 (12)	0.0386 (13)	0.0070 (10)	0.0097 (10)	0.0058 (10)
C15	0.0442 (16)	0.0480 (15)	0.0527 (16)	0.0152 (12)	0.0265 (13)	0.0218 (13)
C16	0.0529 (18)	0.0647 (17)	0.0274 (12)	0.0351 (15)	0.0179 (12)	0.0162 (13)
C17	0.0471 (17)	0.0592 (16)	0.0262 (12)	0.0264 (14)	0.0002 (12)	−0.0033 (12)
C18	0.0320 (13)	0.0384 (12)	0.0350 (12)	0.0117 (10)	0.0061 (10)	−0.0024 (10)

S1—O2	1.4246 (14)	C5—H5	0.9500
S1—O1	1.4291 (15)	C6—H6	0.9500
S1—O3	1.6198 (16)	C7—C8	1.378 (3)
S1—C1	1.750 (2)	C7—C12	1.391 (3)
S2—O8	1.4274 (16)	C8—C9	1.389 (3)
S2—O7	1.4291 (15)	C8—H8	0.9500
S2—O6	1.6069 (17)	C9—C10	1.386 (3)
S2—C13	1.758 (2)	C9—H9	0.9500
O3—C7	1.401 (2)	C10—C11	1.384 (3)
O4—N1	1.225 (2)	C11—C12	1.387 (3)
O5—N1	1.226 (2)	C11—H11	0.9500
O6—C10	1.411 (2)	C13—C14	1.380 (3)
N1—C12	1.474 (2)	C13—C18	1.393 (3)
C1—C6	1.394 (3)	C14—C15	1.395 (3)
C1—C2	1.398 (3)	C14—H14	0.9500
C2—C3	1.393 (3)	C15—C16	1.373 (4)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.383 (3)	C16—C17	1.385 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.388 (3)	C17—C18	1.375 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.379 (3)	C18—H18	0.9500
O2—S1—O1	121.30 (9)	C8—C7—O3	118.26 (18)
O2—S1—O3	102.71 (8)	C12—C7—O3	121.64 (17)
O1—S1—O3	108.31 (8)	C7—C8—C9	120.0 (2)
O2—S1—C1	109.73 (9)	C7—C8—H8	120.0
O1—S1—C1	109.68 (9)	C9—C8—H8	120.0
O3—S1—C1	103.42 (9)	C10—C9—C8	118.85 (19)
O8—S2—O7	121.12 (10)	C10—C9—H9	120.6
O8—S2—O6	108.61 (9)	C8—C9—H9	120.6
O7—S2—O6	102.61 (9)	C11—C10—C9	122.31 (19)
O8—S2—C13	109.46 (10)	C11—C10—O6	118.83 (18)
O7—S2—C13	110.01 (10)	C9—C10—O6	118.65 (17)
O6—S2—C13	103.41 (9)	C10—C11—C12	117.65 (19)
C7—O3—S1	116.62 (12)	C10—C11—H11	121.2
C10—O6—S2	118.49 (12)	C12—C11—H11	121.2
O4—N1—O5	124.14 (17)	C11—C12—C7	121.03 (18)
O4—N1—C12	118.28 (17)	C11—C12—N1	116.91 (18)
O5—N1—C12	117.56 (16)	C7—C12—N1	122.06 (17)
C6—C1—C2	122.0 (2)	C14—C13—C18	121.6 (2)
C6—C1—S1	118.36 (16)	C14—C13—S2	119.40 (17)
C2—C1—S1	119.60 (16)	C18—C13—S2	118.99 (18)
C3—C2—C1	117.77 (19)	C13—C14—C15	118.7 (2)
C3—C2—H2	121.1	C13—C14—H14	120.7
C1—C2—H2	121.1	C15—C14—H14	120.7
C4—C3—C2	120.8 (2)	C16—C15—C14	120.0 (3)
C4—C3—H3	119.6	C16—C15—H15	120.0
C2—C3—H3	119.6	C14—C15—H15	120.0
C3—C4—C5	120.3 (2)	C15—C16—C17	120.7 (2)
C3—C4—H4	119.9	C15—C16—H16	119.7
C5—C4—H4	119.9	C17—C16—H16	119.7
C6—C5—C4	120.5 (2)	C18—C17—C16	120.3 (2)
C6—C5—H5	119.7	C18—C17—H17	119.9
C4—C5—H5	119.7	C16—C17—H17	119.9
C5—C6—C1	118.6 (2)	C17—C18—C13	118.8 (2)
C5—C6—H6	120.7	C17—C18—H18	120.6
C1—C6—H6	120.7	C13—C18—H18	120.6
C8—C7—C12	120.10 (18)
O2—S1—O3—C7	−161.01 (14)	S2—O6—C10—C9	−95.9 (2)
O1—S1—O3—C7	−31.54 (16)	C9—C10—C11—C12	−1.1 (3)
C1—S1—O3—C7	84.81 (15)	O6—C10—C11—C12	173.68 (17)
O8—S2—O6—C10	37.06 (17)	C10—C11—C12—C7	−1.8 (3)
O7—S2—O6—C10	166.41 (14)	C10—C11—C12—N1	178.80 (17)
C13—S2—O6—C10	−79.15 (16)	C8—C7—C12—C11	3.0 (3)
O2—S1—C1—C6	−33.48 (19)	O3—C7—C12—C11	−177.22 (17)
O1—S1—C1—C6	−169.09 (16)	C8—C7—C12—N1	−177.57 (18)
O3—S1—C1—C6	75.54 (18)	O3—C7—C12—N1	2.2 (3)
O2—S1—C1—C2	145.86 (17)	O4—N1—C12—C11	−151.69 (18)
O1—S1—C1—C2	10.3 (2)	O5—N1—C12—C11	27.0 (3)
O3—S1—C1—C2	−105.11 (17)	O4—N1—C12—C7	28.9 (3)
C6—C1—C2—C3	0.7 (3)	O5—N1—C12—C7	−152.42 (19)
S1—C1—C2—C3	−178.60 (17)	O8—S2—C13—C14	12.8 (2)
C1—C2—C3—C4	0.7 (3)	O7—S2—C13—C14	−122.56 (18)
C2—C3—C4—C5	−2.1 (4)	O6—S2—C13—C14	128.44 (17)
C3—C4—C5—C6	2.1 (4)	O8—S2—C13—C18	−168.81 (16)
C4—C5—C6—C1	−0.6 (3)	O7—S2—C13—C18	55.8 (2)
C2—C1—C6—C5	−0.8 (3)	O6—S2—C13—C18	−53.20 (18)
S1—C1—C6—C5	178.57 (17)	C18—C13—C14—C15	−0.7 (3)
S1—O3—C7—C8	−97.86 (18)	S2—C13—C14—C15	177.62 (17)
S1—O3—C7—C12	82.4 (2)	C13—C14—C15—C16	0.7 (3)
C12—C7—C8—C9	−1.4 (3)	C14—C15—C16—C17	−0.1 (4)
O3—C7—C8—C9	178.82 (17)	C15—C16—C17—C18	−0.6 (4)
C7—C8—C9—C10	−1.3 (3)	C16—C17—C18—C13	0.6 (3)
C8—C9—C10—C11	2.6 (3)	C14—C13—C18—C17	0.0 (3)
C8—C9—C10—O6	−172.13 (17)	S2—C13—C18—C17	−178.28 (17)
S2—O6—C10—C11	89.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4i	0.95	2.49	3.234 (3)	135
C9—H9···O8ii	0.95	2.46	3.368 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4i	0.95	2.49	3.234 (3)	135
C9—H9⋯O8ii	0.95	2.46	3.368 (3)	160

Symmetry codes: (i) ; (ii) .