1,3-Bis{[(4-methyl­phen­yl)sulfon­yl]­oxy}propan-2-yl 4-methyl­benzene­sulfonate

Yusof, Y.A.; Ariffin, A.; Abu Hassan, H.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812008227

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o909-o910

doi:10.1107/S1600536812008227

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1,3-Bis{[(4-methylphenyl)sulfonyl]oxy}propan-2-yl 4-methylbenzenesulfonate

Yusrabbil Amiyati Yusof,^a Azhar Ariffin,^a ‡ Hazimah Abu Hassan,^b Seik Weng Ng ^a,^c and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^bMalaysian Palm Oil Board, Bandar Baru Bangi, 43000 Bangi, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 20 February 2012; accepted 23 February 2012; online 29 February 2012)

In the title sulfonate derivative, C₂₄H₂₆O₉S₃, all atoms apart from those of one of the 4-methylbenzenesulfonate residues lie approximately in a disc; the dihedral angles between the approximately orthogonal benzene ring and those in the plane are 74.53 (9) and 67.79 (11)°. In the crystal, molecules are consolidated into the three-dimensional architecture by C—H⋯O interactions. One of the 4-methylbenzenesulfonate residues is disordered over two almost parallel positions; the major component refined to a site-occupancy factor of 0.918 (2).

Related literature

For use of the title compound as a stabilizer for thermal recording materials, see: Matsumoto et al. (1996 ). For a related structure, see: Al-Mohammed et al. (2011 ).

Experimental

Crystal data

C₂₄H₂₆O₉S₃
M_r = 554.63
Triclinic, $[P \overline 1]$
a = 7.6887 (3) Å
b = 12.9635 (5) Å
c = 13.6887 (5) Å
α = 98.943 (3)°
β = 100.292 (3)°
γ = 105.174 (3)°
V = 1265.91 (8) Å³
Z = 2
Cu Kα radiation
μ = 3.13 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.407, T_max = 0.508
9241 measured reflections
5191 independent reflections
4801 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.100
S = 1.06
5191 reflections
363 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	0.99	2.58	3.430 (2)	144
C3—H3A⋯O2ⁱ	0.99	2.39	3.230 (2)	143
C3—H3B⋯O9ⁱⁱ	0.99	2.53	3.377 (2)	144
C6—H6⋯O4ⁱⁱⁱ	0.95	2.51	3.332 (2)	145
C9—H9⋯O5^iv	0.95	2.50	3.166 (2)	127
C15—H15⋯O6^v	0.95	2.53	3.409 (4)	154
C20—H20⋯O3^vi	0.95	2.60	3.545 (2)	176
C24—H24B⋯O8^vii	0.98	2.55	3.263 (3)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+2; (v) x-1, y, z; (vi) x, y+1, z; (vii) -x, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008227/jj2124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008227/jj2124Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008227/jj2124Isup3.cml

checkCIF report

Comment top

In continuation of the related structural studies (Al-Mohammed et al., 2011), the crystal structure determination of the title compound, (I), is now described. Compound (I) has been patented as a stabilizer for thermal recording materials (Matsumoto et al., 1996).

In (I), Fig. 1, each carbon of the propyl residue is connected to a 4-methylbenzenesulfonate residue. The S1- and S2-containing residues are approximately co-planar with the central propyl chain with the dihedral angle between their benzene rings being 51.00 (11)°. By contrast, the S3-containing 4-methylbenzenesulfonate projects almost orthogonally with respect to the remaining molecule. The dihedral angles between the benzene ring of the S3-residue and those of the S1- and S2- residues are 74.53 (9) and 67.79 (11)°, respectively.

Molecules are consolidated into the three-dimensional architecture by weak C—H···O interactions, Table 1. Globally, the crystal structure comprises alternating layers of sulfonate-rich and sulfonate-poor regions that stack along the b axis, Fig. 2.

Related literature top

For use of the title compound as a stabilizer for thermal recording materials, see: Matsumoto et al. (1996). For a related structure, see: Al-Mohammed et al. (2011).

Experimental top

Glycerol (5.53 g, 0.06 mol), pyridine (4 ml, excess) and p-toluenesulfonyl chloride (9.53 g, 0.05 mol) was stirred in dichloromethane (50 ml) and monitored by thin layer chromatography. On completion of the reaction, dilute hydrochloric acid was added and the product was purified by column chromatography. Crystals were obtained upon recrystallization from its n-hexane/ether solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major component of the disordered residue is shown.
	Fig. 2. A view in projection down the a axis of the unit-cell contents of (I). The weak C—H···O interactions are shown as orange dashed lines.

1,3-Bis{[(4-methylphenyl)sulfonyl]oxy}propan-2-yl 4-methylbenzenesulfonate top

Crystal data top

C₂₄H₂₆O₉S₃	Z = 2
M_r = 554.63	F(000) = 580
Triclinic, P1	D_x = 1.455 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.6887 (3) Å	Cell parameters from 5203 reflections
b = 12.9635 (5) Å	θ = 3.4–76.0°
c = 13.6887 (5) Å	µ = 3.13 mm⁻¹
α = 98.943 (3)°	T = 100 K
β = 100.292 (3)°	Prism, colorless
γ = 105.174 (3)°	0.35 × 0.30 × 0.25 mm
V = 1265.91 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5191 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4801 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.2°, θ_min = 3.4°
ω scan	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→16
T_min = 0.407, T_max = 0.508	l = −16→17
9241 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0582P)² + 0.5065P] where P = (F_o² + 2F_c²)/3
5191 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.44 e Å⁻³
22 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₂₄H₂₆O₉S₃	γ = 105.174 (3)°
M_r = 554.63	V = 1265.91 (8) Å³
Triclinic, P1	Z = 2
a = 7.6887 (3) Å	Cu Kα radiation
b = 12.9635 (5) Å	µ = 3.13 mm⁻¹
c = 13.6887 (5) Å	T = 100 K
α = 98.943 (3)°	0.35 × 0.30 × 0.25 mm
β = 100.292 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5191 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4801 reflections with I > 2σ(I)
T_min = 0.407, T_max = 0.508	R_int = 0.018
9241 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	22 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.06	Δρ_max = 0.44 e Å⁻³
5191 reflections	Δρ_min = −0.53 e Å⁻³
363 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.49448 (5)	0.37561 (3)	0.65879 (3)	0.02049 (11)
S2	0.51107 (6)	0.76065 (4)	0.89915 (3)	0.02057 (14)	0.9178 (19)
O4	0.40477 (17)	0.66335 (10)	0.80445 (9)	0.0204 (3)	0.9178 (19)
O5	0.46255 (18)	0.71611 (11)	0.98305 (10)	0.0256 (3)	0.9178 (19)
O6	0.70049 (18)	0.79885 (12)	0.89449 (10)	0.0289 (3)	0.9178 (19)
S2'	0.5610 (6)	0.8258 (4)	0.8805 (3)	0.02057 (14)	0.08
O4'	0.5398 (17)	0.7696 (8)	0.7667 (6)	0.0204 (3)	0.08
O5'	0.497 (2)	0.7436 (11)	0.9354 (11)	0.0256 (3)	0.08
O6'	0.7505 (13)	0.8922 (11)	0.9127 (10)	0.0289 (3)	0.08
C11	0.4061 (3)	0.86328 (16)	0.88221 (14)	0.0214 (4)	0.9178 (19)
C12	0.5056 (3)	0.96078 (18)	0.86304 (14)	0.0258 (4)	0.9178 (19)
H12	0.6311	0.9727	0.8590	0.031*	0.9178 (19)
C13	0.4191 (3)	1.04095 (18)	0.84975 (15)	0.0294 (4)	0.9178 (19)
H13	0.4862	1.1078	0.8361	0.035*	0.9178 (19)
C14	0.2354 (3)	1.02465 (17)	0.85616 (16)	0.0282 (4)	0.9178 (19)
C15	0.1377 (5)	0.92566 (19)	0.8755 (3)	0.0283 (6)	0.9178 (19)
H15	0.0120	0.9134	0.8794	0.034*	0.9178 (19)
C16	0.2227 (3)	0.8451 (2)	0.8892 (3)	0.0258 (5)	0.9178 (19)
H16	0.1563	0.7783	0.9031	0.031*	0.9178 (19)
C17	0.1398 (4)	1.11140 (18)	0.83952 (17)	0.0377 (5)	0.9178 (19)
H17A	0.1399	1.1537	0.9054	0.057*	0.9178 (19)
H17B	0.0119	1.0761	0.8008	0.057*	0.9178 (19)
H17C	0.2061	1.1604	0.8016	0.057*	0.9178 (19)
C11'	0.418 (3)	0.9037 (19)	0.8732 (19)	0.0214 (4)	0.08
C12'	0.478 (3)	1.008 (2)	0.8559 (18)	0.0258 (4)	0.08
H12'	0.6025	1.0353	0.8506	0.031*	0.0822 (19)
C13'	0.366 (3)	1.0741 (18)	0.8462 (19)	0.0294 (4)	0.08
H13'	0.4131	1.1435	0.8308	0.035*	0.0822 (19)
C14'	0.186 (3)	1.0435 (19)	0.858 (2)	0.0282 (4)	0.08
C15'	0.133 (5)	0.942 (3)	0.888 (5)	0.0283 (6)	0.08
H15'	0.0250	0.9251	0.9139	0.034*	0.0822 (19)
C16'	0.231 (4)	0.869 (2)	0.880 (4)	0.0258 (5)	0.08
H16'	0.1739	0.7942	0.8799	0.031*	0.0822 (19)
C17'	0.056 (4)	1.114 (2)	0.863 (2)	0.0377 (5)	0.08
H17D	0.1152	1.1862	0.8505	0.057*	0.0822 (19)
H17E	0.0267	1.1227	0.9297	0.057*	0.0822 (19)
H17F	−0.0591	1.0787	0.8103	0.057*	0.0822 (19)
S3	−0.00968 (5)	0.71736 (3)	0.58851 (3)	0.02206 (11)
O1	0.43925 (15)	0.48154 (9)	0.69633 (9)	0.0210 (2)
O2	0.52903 (18)	0.37663 (11)	0.55959 (9)	0.0296 (3)
O3	0.35248 (16)	0.28856 (10)	0.67462 (10)	0.0288 (3)
O7	0.16164 (16)	0.70724 (10)	0.66600 (9)	0.0237 (2)
O8	−0.11727 (17)	0.75505 (11)	0.65271 (11)	0.0308 (3)
O9	−0.08818 (17)	0.61688 (10)	0.51449 (10)	0.0304 (3)
C1	0.5531 (2)	0.58641 (13)	0.68525 (13)	0.0223 (3)
H1A	0.5740	0.5812	0.6156	0.027*
H1B	0.6747	0.6093	0.7342	0.027*
C2	0.4473 (2)	0.66703 (14)	0.70636 (12)	0.0230 (3)
H2	0.5262	0.7423	0.7078	0.028*	0.9178 (19)
H2'	0.3914	0.6346	0.7594	0.028*	0.0822 (19)
C3	0.2684 (2)	0.64029 (14)	0.62715 (12)	0.0220 (3)
H3A	0.2944	0.6568	0.5621	0.026*
H3B	0.1993	0.5618	0.6154	0.026*
C4	0.7047 (2)	0.39166 (13)	0.74391 (12)	0.0201 (3)
C5	0.8713 (2)	0.44346 (14)	0.72137 (14)	0.0258 (3)
H5	0.8721	0.4721	0.6616	0.031*
C6	1.0356 (2)	0.45229 (15)	0.78773 (15)	0.0296 (4)
H6	1.1499	0.4873	0.7729	0.036*
C7	1.0371 (2)	0.41095 (14)	0.87563 (15)	0.0294 (4)
C8	0.8685 (3)	0.36109 (16)	0.89672 (15)	0.0328 (4)
H8	0.8677	0.3331	0.9568	0.039*
C9	0.7014 (2)	0.35129 (15)	0.83185 (14)	0.0271 (4)
H9	0.5871	0.3176	0.8474	0.033*
C10	1.2193 (3)	0.41970 (18)	0.94442 (19)	0.0421 (5)
H10A	1.2981	0.4959	0.9616	0.063*
H10B	1.2813	0.3732	0.9096	0.063*
H10C	1.1971	0.3958	1.0068	0.063*
C18	0.0922 (2)	0.82229 (13)	0.53146 (12)	0.0198 (3)
C19	0.1481 (2)	0.92984 (13)	0.58581 (13)	0.0230 (3)
H19	0.1269	0.9462	0.6520	0.028*
C20	0.2351 (2)	1.01301 (14)	0.54257 (14)	0.0261 (3)
H20	0.2727	1.0867	0.5792	0.031*
C21	0.2679 (2)	0.98960 (15)	0.44573 (14)	0.0269 (4)
C22	0.2096 (3)	0.88154 (16)	0.39294 (14)	0.0299 (4)
H22	0.2310	0.8649	0.3269	0.036*
C23	0.1207 (3)	0.79717 (15)	0.43453 (13)	0.0273 (4)
H23	0.0803	0.7236	0.3973	0.033*
C24	0.3618 (3)	1.08080 (18)	0.39891 (17)	0.0371 (4)
H24A	0.4166	1.1482	0.4513	0.056*
H24B	0.2704	1.0923	0.3452	0.056*
H24C	0.4592	1.0610	0.3698	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01969 (19)	0.01871 (19)	0.0219 (2)	0.00439 (15)	0.00552 (14)	0.00246 (14)
S2	0.0209 (2)	0.0224 (2)	0.0183 (2)	0.00569 (16)	0.00477 (16)	0.00529 (16)
O4	0.0244 (6)	0.0206 (6)	0.0175 (6)	0.0059 (5)	0.0077 (5)	0.0059 (5)
O5	0.0321 (7)	0.0287 (7)	0.0184 (6)	0.0096 (6)	0.0073 (5)	0.0090 (5)
O6	0.0200 (6)	0.0320 (7)	0.0309 (7)	0.0038 (5)	0.0038 (5)	0.0053 (6)
S2'	0.0209 (2)	0.0224 (2)	0.0183 (2)	0.00569 (16)	0.00477 (16)	0.00529 (16)
O4'	0.0244 (6)	0.0206 (6)	0.0175 (6)	0.0059 (5)	0.0077 (5)	0.0059 (5)
O5'	0.0321 (7)	0.0287 (7)	0.0184 (6)	0.0096 (6)	0.0073 (5)	0.0090 (5)
O6'	0.0200 (6)	0.0320 (7)	0.0309 (7)	0.0038 (5)	0.0038 (5)	0.0053 (6)
C11	0.0262 (9)	0.0190 (9)	0.0185 (8)	0.0058 (8)	0.0054 (6)	0.0032 (7)
C12	0.0289 (9)	0.0231 (10)	0.0230 (9)	0.0040 (9)	0.0067 (7)	0.0032 (7)
C13	0.0390 (12)	0.0195 (10)	0.0260 (9)	0.0042 (8)	0.0044 (8)	0.0051 (8)
C14	0.0389 (12)	0.0232 (10)	0.0186 (8)	0.0117 (8)	−0.0028 (9)	−0.0001 (7)
C15	0.0279 (9)	0.0284 (12)	0.0260 (16)	0.0091 (9)	0.0026 (8)	0.0015 (13)
C16	0.0246 (8)	0.0254 (13)	0.0268 (11)	0.0053 (9)	0.0063 (7)	0.0069 (10)
C17	0.0491 (14)	0.0290 (10)	0.0318 (11)	0.0166 (10)	−0.0024 (9)	0.0021 (8)
C11'	0.0262 (9)	0.0190 (9)	0.0185 (8)	0.0058 (8)	0.0054 (6)	0.0032 (7)
C12'	0.0289 (9)	0.0231 (10)	0.0230 (9)	0.0040 (9)	0.0067 (7)	0.0032 (7)
C13'	0.0390 (12)	0.0195 (10)	0.0260 (9)	0.0042 (8)	0.0044 (8)	0.0051 (8)
C14'	0.0389 (12)	0.0232 (10)	0.0186 (8)	0.0117 (8)	−0.0028 (9)	−0.0001 (7)
C15'	0.0279 (9)	0.0284 (12)	0.0260 (16)	0.0091 (9)	0.0026 (8)	0.0015 (13)
C16'	0.0246 (8)	0.0254 (13)	0.0268 (11)	0.0053 (9)	0.0063 (7)	0.0069 (10)
C17'	0.0491 (14)	0.0290 (10)	0.0318 (11)	0.0166 (10)	−0.0024 (9)	0.0021 (8)
S3	0.01781 (19)	0.0201 (2)	0.0277 (2)	0.00455 (14)	0.00356 (15)	0.00722 (15)
O1	0.0194 (5)	0.0187 (5)	0.0269 (6)	0.0051 (4)	0.0098 (4)	0.0065 (4)
O2	0.0333 (7)	0.0351 (7)	0.0205 (6)	0.0119 (5)	0.0077 (5)	0.0015 (5)
O3	0.0222 (6)	0.0202 (6)	0.0395 (7)	0.0006 (5)	0.0050 (5)	0.0051 (5)
O7	0.0247 (6)	0.0274 (6)	0.0212 (6)	0.0126 (5)	0.0034 (4)	0.0055 (5)
O8	0.0252 (6)	0.0324 (7)	0.0424 (7)	0.0118 (5)	0.0156 (5)	0.0157 (6)
O9	0.0252 (6)	0.0183 (6)	0.0396 (7)	0.0018 (5)	−0.0047 (5)	0.0041 (5)
C1	0.0182 (7)	0.0203 (8)	0.0282 (8)	0.0037 (6)	0.0061 (6)	0.0071 (6)
C2	0.0240 (8)	0.0219 (8)	0.0228 (8)	0.0073 (6)	0.0046 (6)	0.0043 (6)
C3	0.0233 (8)	0.0237 (8)	0.0217 (8)	0.0110 (6)	0.0047 (6)	0.0067 (6)
C4	0.0186 (7)	0.0178 (7)	0.0240 (8)	0.0056 (6)	0.0056 (6)	0.0035 (6)
C5	0.0242 (8)	0.0235 (8)	0.0318 (9)	0.0063 (7)	0.0120 (7)	0.0071 (7)
C6	0.0217 (8)	0.0249 (8)	0.0428 (10)	0.0054 (7)	0.0114 (7)	0.0069 (7)
C7	0.0239 (8)	0.0223 (8)	0.0393 (10)	0.0086 (7)	0.0012 (7)	0.0027 (7)
C8	0.0331 (9)	0.0344 (10)	0.0337 (10)	0.0113 (8)	0.0065 (8)	0.0145 (8)
C9	0.0253 (8)	0.0278 (8)	0.0297 (9)	0.0054 (7)	0.0099 (7)	0.0104 (7)
C10	0.0300 (10)	0.0362 (11)	0.0558 (13)	0.0129 (8)	−0.0044 (9)	0.0083 (9)
C18	0.0170 (7)	0.0202 (7)	0.0213 (7)	0.0056 (6)	0.0020 (6)	0.0049 (6)
C19	0.0214 (7)	0.0221 (8)	0.0228 (8)	0.0037 (6)	0.0055 (6)	0.0015 (6)
C20	0.0225 (8)	0.0199 (8)	0.0345 (9)	0.0047 (6)	0.0067 (7)	0.0045 (7)
C21	0.0230 (8)	0.0307 (9)	0.0342 (9)	0.0131 (7)	0.0096 (7)	0.0155 (7)
C22	0.0369 (9)	0.0356 (10)	0.0243 (8)	0.0171 (8)	0.0119 (7)	0.0107 (7)
C23	0.0338 (9)	0.0236 (8)	0.0240 (8)	0.0116 (7)	0.0040 (7)	0.0019 (6)
C24	0.0329 (10)	0.0400 (11)	0.0500 (12)	0.0156 (8)	0.0172 (9)	0.0267 (9)

Geometric parameters (Å, º) top

S1—O3	1.4241 (13)	S3—O8	1.4258 (13)
S1—O2	1.4309 (12)	S3—O9	1.4308 (13)
S1—O1	1.5792 (11)	S3—O7	1.5848 (12)
S1—C4	1.7574 (16)	S3—C18	1.7506 (16)
S2—O5	1.4276 (13)	O1—C1	1.4581 (18)
S2—O6	1.4268 (14)	O7—C3	1.4478 (19)
S2—O4	1.5853 (13)	C1—C2	1.508 (2)
S2—C11	1.751 (2)	C1—H1A	0.9900
O4—C2	1.4424 (19)	C1—H1B	0.9900
S2'—O5'	1.432 (9)	C2—C3	1.513 (2)
S2'—O6'	1.433 (8)	C2—H2	1.0000
S2'—O4'	1.573 (7)	C2—H2'	1.0000
S2'—C11'	1.68 (2)	C3—H3A	0.9900
O4'—C2	1.382 (8)	C3—H3B	0.9900
C11—C12	1.386 (3)	C4—C9	1.387 (2)
C11—C16	1.391 (3)	C4—C5	1.394 (2)
C12—C13	1.390 (3)	C5—C6	1.384 (3)
C12—H12	0.9500	C5—H5	0.9500
C13—C14	1.393 (3)	C6—C7	1.391 (3)
C13—H13	0.9500	C6—H6	0.9500
C14—C15	1.398 (3)	C7—C8	1.390 (3)
C14—C17	1.519 (3)	C7—C10	1.509 (3)
C15—C16	1.387 (3)	C8—C9	1.389 (3)
C15—H15	0.9500	C8—H8	0.9500
C16—H16	0.9500	C9—H9	0.9500
C17—H17A	0.9800	C10—H10A	0.9800
C17—H17B	0.9800	C10—H10B	0.9800
C17—H17C	0.9800	C10—H10C	0.9800
C11'—C12'	1.382 (18)	C18—C23	1.387 (2)
C11'—C16'	1.416 (18)	C18—C19	1.390 (2)
C12'—C13'	1.370 (18)	C19—C20	1.387 (2)
C12'—H12'	0.9500	C19—H19	0.9500
C13'—C14'	1.377 (17)	C20—C21	1.396 (3)
C13'—H13'	0.9500	C20—H20	0.9500
C14'—C15'	1.412 (18)	C21—C22	1.388 (3)
C14'—C17'	1.529 (17)	C21—C24	1.511 (2)
C15'—C16'	1.365 (18)	C22—C23	1.389 (3)
C15'—H15'	0.9500	C22—H22	0.9500
C16'—H16'	0.9500	C23—H23	0.9500
C17'—H17D	0.9800	C24—H24A	0.9800
C17'—H17E	0.9800	C24—H24B	0.9800
C17'—H17F	0.9800	C24—H24C	0.9800

O3—S1—O2	120.39 (8)	O1—C1—C2	106.13 (12)
O3—S1—O1	104.08 (7)	O1—C1—H1A	110.5
O2—S1—O1	108.72 (7)	C2—C1—H1A	110.5
O3—S1—C4	109.80 (8)	O1—C1—H1B	110.5
O2—S1—C4	108.35 (8)	C2—C1—H1B	110.5
O1—S1—C4	104.29 (7)	H1A—C1—H1B	108.7
O5—S2—O6	120.42 (8)	O4'—C2—C1	119.5 (6)
O5—S2—O4	103.08 (7)	O4—C2—C1	108.20 (13)
O6—S2—O4	108.83 (8)	O4'—C2—C3	124.5 (6)
O5—S2—C11	109.48 (8)	O4—C2—C3	108.88 (13)
O6—S2—C11	109.22 (9)	C1—C2—C3	111.91 (14)
O4—S2—C11	104.56 (8)	O4—C2—H2	109.3
C2—O4—S2	120.41 (10)	C1—C2—H2	109.3
O5'—S2'—O6'	118.3 (9)	C3—C2—H2	109.3
O5'—S2'—O4'	109.3 (7)	O7—C3—C2	106.89 (13)
O6'—S2'—O4'	104.4 (7)	O7—C3—H3A	110.3
O5'—S2'—C11'	108.9 (11)	C2—C3—H3A	110.3
O6'—S2'—C11'	110.8 (11)	O7—C3—H3B	110.3
O4'—S2'—C11'	104.1 (10)	C2—C3—H3B	110.3
C2—O4'—S2'	135.1 (8)	H3A—C3—H3B	108.6
C12—C11—C16	121.07 (18)	C9—C4—C5	121.26 (16)
C12—C11—S2	120.16 (15)	C9—C4—S1	119.20 (13)
C16—C11—S2	118.77 (15)	C5—C4—S1	119.53 (13)
C11—C12—C13	119.08 (18)	C6—C5—C4	118.72 (16)
C11—C12—H12	120.5	C6—C5—H5	120.6
C13—C12—H12	120.5	C4—C5—H5	120.6
C12—C13—C14	120.92 (18)	C5—C6—C7	121.40 (16)
C12—C13—H13	119.5	C5—C6—H6	119.3
C14—C13—H13	119.5	C7—C6—H6	119.3
C15—C14—C13	119.0 (2)	C8—C7—C6	118.50 (16)
C15—C14—C17	120.1 (2)	C8—C7—C10	121.84 (18)
C13—C14—C17	120.9 (2)	C6—C7—C10	119.65 (18)
C16—C15—C14	120.6 (2)	C7—C8—C9	121.46 (17)
C16—C15—H15	119.7	C7—C8—H8	119.3
C14—C15—H15	119.7	C9—C8—H8	119.3
C15—C16—C11	119.3 (2)	C4—C9—C8	118.64 (16)
C15—C16—H16	120.3	C4—C9—H9	120.7
C11—C16—H16	120.3	C8—C9—H9	120.7
C12'—C11'—C16'	115.4 (17)	C7—C10—H10A	109.5
C12'—C11'—S2'	120.4 (18)	C7—C10—H10B	109.5
C16'—C11'—S2'	124.2 (18)	H10A—C10—H10B	109.5
C11'—C12'—C13'	122.9 (18)	C7—C10—H10C	109.5
C11'—C12'—H12'	118.6	H10A—C10—H10C	109.5
C13'—C12'—H12'	118.6	H10B—C10—H10C	109.5
C12'—C13'—C14'	122.4 (18)	C23—C18—C19	120.99 (15)
C12'—C13'—H13'	118.8	C23—C18—S3	119.93 (13)
C14'—C13'—H13'	118.8	C19—C18—S3	119.05 (12)
C13'—C14'—C15'	114.4 (18)	C20—C19—C18	119.37 (15)
C13'—C14'—C17'	128 (2)	C20—C19—H19	120.3
C15'—C14'—C17'	116.9 (19)	C18—C19—H19	120.3
C16'—C15'—C14'	122 (2)	C19—C20—C21	120.68 (16)
C14'—C15'—H15'	118.8	C19—C20—H20	119.7
C15'—C16'—C11'	120 (2)	C21—C20—H20	119.7
C15'—C16'—H16'	120.1	C22—C21—C20	118.71 (16)
C11'—C16'—H16'	120.1	C22—C21—C24	120.93 (17)
C14'—C17'—H17D	109.5	C20—C21—C24	120.34 (17)
C14'—C17'—H17E	109.5	C21—C22—C23	121.48 (16)
H17D—C17'—H17E	109.5	C21—C22—H22	119.3
C14'—C17'—H17F	109.5	C23—C22—H22	119.3
H17D—C17'—H17F	109.5	C18—C23—C22	118.74 (16)
H17E—C17'—H17F	109.5	C18—C23—H23	120.6
O8—S3—O9	120.40 (8)	C22—C23—H23	120.6
O8—S3—O7	103.60 (7)	C21—C24—H24A	109.5
O9—S3—O7	108.61 (7)	C21—C24—H24B	109.5
O8—S3—C18	109.66 (8)	H24A—C24—H24B	109.5
O9—S3—C18	110.02 (8)	C21—C24—H24C	109.5
O7—S3—C18	102.96 (7)	H24A—C24—H24C	109.5
C1—O1—S1	118.12 (9)	H24B—C24—H24C	109.5
C3—O7—S3	117.53 (10)

O5—S2—O4—C2	−167.25 (12)	S2'—O4'—C2—O4	0.7 (11)
O6—S2—O4—C2	−38.32 (14)	S2'—O4'—C2—C1	−101.6 (12)
C11—S2—O4—C2	78.29 (13)	S2'—O4'—C2—C3	103.1 (12)
O5'—S2'—O4'—C2	13.9 (16)	S2—O4—C2—O4'	−9.5 (6)
O6'—S2'—O4'—C2	141.3 (13)	S2—O4—C2—C1	107.04 (13)
C11'—S2'—O4'—C2	−102.3 (15)	S2—O4—C2—C3	−131.12 (12)
O5—S2—C11—C12	136.50 (15)	O1—C1—C2—O4'	136.3 (5)
O6—S2—C11—C12	2.71 (18)	O1—C1—C2—O4	54.53 (16)
O4—S2—C11—C12	−113.63 (15)	O1—C1—C2—C3	−65.43 (17)
O5—S2—C11—C16	−43.0 (2)	S3—O7—C3—C2	165.70 (10)
O6—S2—C11—C16	−176.8 (2)	O4'—C2—C3—O7	−34.9 (5)
O4—S2—C11—C16	66.9 (2)	O4—C2—C3—O7	48.53 (16)
C16—C11—C12—C13	−0.6 (3)	C1—C2—C3—O7	168.09 (13)
S2—C11—C12—C13	179.93 (15)	O3—S1—C4—C9	−21.13 (16)
C11—C12—C13—C14	0.4 (3)	O2—S1—C4—C9	−154.44 (14)
C12—C13—C14—C15	−0.5 (3)	O1—S1—C4—C9	89.88 (14)
C12—C13—C14—C17	−178.76 (19)	O3—S1—C4—C5	158.15 (13)
C13—C14—C15—C16	0.6 (5)	O2—S1—C4—C5	24.85 (15)
C17—C14—C15—C16	178.9 (3)	O1—S1—C4—C5	−90.84 (14)
C14—C15—C16—C11	−0.7 (5)	C9—C4—C5—C6	1.3 (3)
C12—C11—C16—C15	0.7 (4)	S1—C4—C5—C6	−177.99 (13)
S2—C11—C16—C15	−179.8 (3)	C4—C5—C6—C7	−0.1 (3)
O5'—S2'—C11'—C12'	158 (2)	C5—C6—C7—C8	−0.8 (3)
O6'—S2'—C11'—C12'	26 (2)	C5—C6—C7—C10	178.39 (17)
O4'—S2'—C11'—C12'	−85 (2)	C6—C7—C8—C9	0.5 (3)
O5'—S2'—C11'—C16'	−24 (3)	C10—C7—C8—C9	−178.60 (18)
O6'—S2'—C11'—C16'	−156 (3)	C5—C4—C9—C8	−1.5 (3)
O4'—S2'—C11'—C16'	92 (3)	S1—C4—C9—C8	177.78 (14)
C16'—C11'—C12'—C13'	0 (4)	C7—C8—C9—C4	0.6 (3)
S2'—C11'—C12'—C13'	178 (2)	O8—S3—C18—C23	−147.39 (14)
C11'—C12'—C13'—C14'	3 (4)	O9—S3—C18—C23	−12.79 (16)
C12'—C13'—C14'—C15'	4 (5)	O7—S3—C18—C23	102.83 (14)
C12'—C13'—C14'—C17'	172 (3)	O8—S3—C18—C19	34.45 (15)
C13'—C14'—C15'—C16'	−16 (7)	O9—S3—C18—C19	169.05 (12)
C17'—C14'—C15'—C16'	175 (5)	O7—S3—C18—C19	−75.33 (14)
C14'—C15'—C16'—C11'	20 (8)	C23—C18—C19—C20	−0.5 (2)
C12'—C11'—C16'—C15'	−11 (6)	S3—C18—C19—C20	177.62 (12)
S2'—C11'—C16'—C15'	171 (4)	C18—C19—C20—C21	−0.5 (3)
O3—S1—O1—C1	−176.79 (11)	C19—C20—C21—C22	0.8 (3)
O2—S1—O1—C1	−47.32 (13)	C19—C20—C21—C24	179.63 (16)
C4—S1—O1—C1	68.10 (12)	C20—C21—C22—C23	−0.2 (3)
O8—S3—O7—C3	161.56 (11)	C24—C21—C22—C23	−179.03 (17)
O9—S3—O7—C3	32.45 (13)	C19—C18—C23—C22	1.1 (3)
C18—S3—O7—C3	−84.18 (12)	S3—C18—C23—C22	−177.02 (13)
S1—O1—C1—C2	168.60 (10)	C21—C22—C23—C18	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.99	2.58	3.430 (2)	144
C3—H3A···O2ⁱ	0.99	2.39	3.230 (2)	143
C3—H3B···O9ⁱⁱ	0.99	2.53	3.377 (2)	144
C6—H6···O4ⁱⁱⁱ	0.95	2.51	3.332 (2)	145
C9—H9···O5^iv	0.95	2.50	3.166 (2)	127
C15—H15···O6^v	0.95	2.53	3.409 (4)	154
C20—H20···O3^vi	0.95	2.60	3.545 (2)	176
C24—H24B···O8^vii	0.98	2.55	3.263 (3)	129

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+2; (v) x−1, y, z; (vi) x, y+1, z; (vii) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆O₉S₃
M_r	554.63
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.6887 (3), 12.9635 (5), 13.6887 (5)
α, β, γ (°)	98.943 (3), 100.292 (3), 105.174 (3)
V (Å³)	1265.91 (8)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.13
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.407, 0.508
No. of measured, independent and observed [I > 2σ(I)] reflections	9241, 5191, 4801
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.100, 1.06
No. of reflections	5191
No. of parameters	363
No. of restraints	22
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.53

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.99	2.58	3.430 (2)	144
C3—H3A···O2ⁱ	0.99	2.39	3.230 (2)	143
C3—H3B···O9ⁱⁱ	0.99	2.53	3.377 (2)	144
C6—H6···O4ⁱⁱⁱ	0.95	2.51	3.332 (2)	145
C9—H9···O5^iv	0.95	2.50	3.166 (2)	127
C15—H15···O6^v	0.95	2.53	3.409 (4)	154
C20—H20···O3^vi	0.95	2.60	3.545 (2)	176
C24—H24B···O8^vii	0.98	2.55	3.263 (3)	129

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+2; (v) x−1, y, z; (vi) x, y+1, z; (vii) −x, −y+2, −z+1.

Footnotes

‡Additional correspondence author, e-mail: azhar70@um.edu.my.

Acknowledgements

The authors thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Mohammed, N. N., Shakir, R. M., Alias, Y., Abdullah, Z., Abd Halim, S. N. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o1838. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Matsumoto, T., Nonaka, H. & Yamaguchi, Y. (1996). Jpn Kokai Tokyo Koho, JP 08276655 A 19961022. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Pages o909-o910

doi:10.1107/S1600536812008227

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,3-Bis{[(4-methyl­phen­yl)sulfon­yl]­­oxy}propan-2-yl 4-methyl­benzene­sulfonate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

1,3-Bis{[(4-methylphenyl)sulfonyl]oxy}propan-2-yl 4-methylbenzenesulfonate