2-Nitro-p-phenyl­ene dibenzene­sulfonate

Yang, Z.

doi:10.1107/S1600536810002898

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o482

https://doi.org/10.1107/S1600536810002898

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2-Nitro-p-phenylene dibenzenesulfonate

Zongwei Yang ^a ^*

^aSichuan College of Chemical Technology, Luzhou 646005, People's Republic of China
^*Correspondence e-mail: yzwchem@126.com

(Received 14 January 2010; accepted 23 January 2010; online 30 January 2010)

In the title compound, C₁₈H₁₃NO₈S₂, the nitrophenyl 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 intermolecular 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_r = 435.43
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.121
S = 1.08
4386 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −0.50 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002898/bq2192Isup2.hkl

checkCIF report

Comment top

Phenolic esters can be used to synthesize some useful intermediates in organic synthesis (Trollsås et al., 1996; Svensson et al., 1998; Atkinson et al., 2005; Hu et al., 2001).

The compound (I) was prepared by the reaction of 2-nitrohydroquinone and 4-phenylsulfonyl chloride in the presence of triethylamine (Ji et al., 2006) and its structure was reported here.

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The three aromatic rings ((C1 to C6), (C7 to C12) and (C13 to C18) form two dihedral angles of 46.67 (7)° and 75.40 (6)° in turn. The nitro group plane is connected with the aromatic plane with a dihedral angle of 26.13 (8)°. The torsion angles of C1—S1—O3—C7 and C10—O6—S2—C13 are 84.81 (15)° and -79.15 (16)°, respectively. In the crystal structure, intermolecular C—H···O hydrogen bonds link the molecules (Table 1, Figure 2).

Related literature top

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 top

2-nitrohydroquinone (78 mg, 0.5 mmol) was dissolved in chloroform (30 ml). To this solution, 4-phenylsulfonyl chloride (209 mg, 1.0 mmol) and triethylamine (101 mg, 1.0 mmol) were added and the reaction was stirred at room temperature for 3 h. The reaction mixture was extracted with dichloromethane and dried with anhydrous sodium sulphate. After concentration, the residue was separated by flash column chromatography and purified by recrystallization from chloroform (yield 156 mg, 72%, m.p. 393 K). Spectroscopic analysis: IR (KBr, ν, cm^-1): 3075, 1541, 1483, 1379, 1198, 1165, 1091, 855, 733.

Structure description top

Phenolic esters can be used to synthesize some useful intermediates in organic synthesis (Trollsås et al., 1996; Svensson et al., 1998; Atkinson et al., 2005; Hu et al., 2001).

The compound (I) was prepared by the reaction of 2-nitrohydroquinone and 4-phenylsulfonyl chloride in the presence of triethylamine (Ji et al., 2006) and its structure was reported here.

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).

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, (I), with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal structure of (I), view along the a-axis. Dashed lines indicate C—H···O interactions.

2-Nitro-p-phenylene dibenzenesulfonate top

Crystal data top

C₁₈H₁₃NO₈S₂	F(000) = 896
M_r = 435.43	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0646P)²] where P = (F_o² + 2F_c²)/3
4386 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₈H₁₃NO₈S₂	V = 1851.9 (14) Å³
M_r = 435.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.669 (5) Å	µ = 0.34 mm⁻¹
b = 10.554 (4) Å	T = 113 K
c = 15.343 (7) Å	0.30 × 0.07 × 0.06 mm
β = 101.462 (7)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	4386 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007)	3278 reflections with I > 2σ(I)
T_min = 0.906, T_max = 0.980	R_int = 0.035
15174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.08	Δρ_max = 1.11 e Å⁻³
4386 reflections	Δρ_min = −0.50 e Å⁻³
262 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₃NO₈S₂
M_r	435.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	11.669 (5), 10.554 (4), 15.343 (7)
β (°)	101.462 (7)
V (Å³)	1851.9 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.07 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2007)
T_min, T_max	0.906, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	15174, 4386, 3278
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.121, 1.08
No. of reflections	4386
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.50

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.9500	2.49	3.234 (3)	134.7
C9—H9···O8ⁱⁱ	0.9500	2.46	3.368 (3)	159.7

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

References

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