2-Methyl-3-[(4-methyl­phen­yl)sulfon­yl­oxy]-2-{[(4-methyl­phen­yl)sulfon­yloxy]meth­yl}propyl 4-methyl­benzene­sulfonate

Al-Mohammed, N.N.; Shakir, R.M.; Alias, Y.; Abdullah, Z.; Abd Halim, S.N.; Tiekink, E.R.T.

doi:10.1107/S1600536811024664

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1838

doi:10.1107/S1600536811024664

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2-Methyl-3-[(4-methylphenyl)sulfonyloxy]-2-{[(4-methylphenyl)sulfonyloxy]methyl}propyl 4-methylbenzenesulfonate

Nassir N. Al-Mohammed,^a Raied M. Shakir,^a Yatimah Alias,^a ‡ Zanariah Abdullah,^a Siti Nadiah Abd Halim ^a and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 21 June 2011; accepted 22 June 2011; online 30 June 2011)

The title molecule, C₂₆H₃₀O₉S₃, adopts an extended conformation whereby two approximately parallel benzene rings [dihedral angle = 8.32 (10)°] are orientated in opposite directions along the pseudo-threefold axis through the central quaternary C atom, while a third ring occupies a position mid-way and face-on to these rings [dihedral angles = 82.28 (10) and 78.81 (7)°]. The crystal packing is dominated by C—H⋯O contacts and π–π interactions [ring centroid distance = 3.6902 (12) Å].

Related literature

For the use of molecules related to the title compound as synthetic precursors, see: Laliberte et al. (2003 ); Fujihara et al. (2007 ); Li et al. (2008a ,b ).

Experimental

Crystal data

C₂₆H₃₀O₉S₃
M_r = 582.68
Triclinic, $[P \overline 1]$
a = 10.2055 (3) Å
b = 12.4029 (3) Å
c = 12.7993 (4) Å
α = 66.868 (2)°
β = 78.370 (2)°
γ = 68.085 (2)°
V = 1379.32 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.30 × 0.28 × 0.28 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.636, T_max = 0.746
13040 measured reflections
6305 independent reflections
5369 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.117
S = 0.99
6303 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2b⋯O2ⁱ	0.99	2.49	3.297 (2)	138
C4—H4a⋯O2ⁱ	0.99	2.42	3.290 (2)	147
C5—H5c⋯O8ⁱⁱ	0.98	2.54	3.440 (2)	152
C7—H7⋯O6ⁱ	0.95	2.54	3.183 (2)	125
C10—H10⋯O3ⁱⁱⁱ	0.95	2.54	3.358 (2)	144
C15—H15⋯O9^iv	0.95	2.56	3.428 (3)	151
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+2, -z+1; (iv) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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/S1600536811024664/hg5057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024664/hg5057Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024664/hg5057Isup3.cml

checkCIF report

Comment top

Molecules related to the title compound, (I), are useful synthetic precursors for dendritic materials (Laliberte et al., 2003), branched acyclic polyamines (Fujihara et al., 2007) and radiopharmaceuticals (Li et al., 2008a; Li et al., 2008b).

With reference to the methyl group in the trisubstituted methane molecule, one benzene ring, connected to atom S1, is orientated in the same direction, and another, connected to S3, is approximately parallel but orientated in the opposite direction; dihedral angle = 8.32 (10) °. The third benzene ring lies approximately half-way between these rings and is face-on to each, forming dihedral angles of 82.28 (10) (S1) and 78.81 (7) °, respectively. This arrangement contrasts sharply the observed structure of the "parent" compound which adopts a somewhat flattened geometry with all benzene rings orientated in a circular manner around the central residue (Fujihara et al., 2007).

The molecules are consolidated in the crystal structure by a combination of C—H···O, Table 1, and π–π interactions. The latter occur between centrosymmetrically related C13–C18 rings [3.6902 (12) Å for symmetry operation 2 - x, 1 - y, 2 - z]. Globally, layers of molecule interdigitate along the c axis, Fig. 2.

Related literature top

For the use of molecules related to the title compound as synthetic precursors, see: Laliberte et al. (2003); Fujihara et al. (2007); Li et al. (2008a,b).

Experimental top

p-Toluenesulfonyl chloride (5.23 g, 27.4 mmol) in dry dichloromethane (50 ml) was added drop wise to a stirring solution of 1,1,1-tris(hydroxymethyl)ethane (1 g, 8.32 mmol) and triethylamine (5.05 g, 0.50 mmol) in dichloromethane (50 ml) at 273 K. The mixture was stirred at room temperature overnight, extracted with water, and wasted with distilled water (3 x 10 ml). The organic layer was dried over MgSO₄ and evaporated. Colourless crystals were obtained from slow evaporation from its THF solution, M.pt 373–375 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 compound (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents for (I). The C—H···O and π–π interactions are shown as orange and purple dashed lines, respectively.

2-Methyl-3-[(4-methylphenyl)sulfonyloxy]-2-{[(4- methylphenyl)sulfonyloxy]methyl}propyl 4-methylbenzenesulfonate top

Crystal data top

C₂₆H₃₀O₉S₃	Z = 2
M_r = 582.68	F(000) = 612
Triclinic, P1	D_x = 1.403 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2055 (3) Å	Cell parameters from 5679 reflections
b = 12.4029 (3) Å	θ = 2.4–30.6°
c = 12.7993 (4) Å	µ = 0.32 mm⁻¹
α = 66.868 (2)°	T = 100 K
β = 78.370 (2)°	Block, yellow
γ = 68.085 (2)°	0.30 × 0.28 × 0.28 mm
V = 1379.32 (7) Å³

Data collection top

Bruker SMART APEX diffractometer	6305 independent reflections
Radiation source: fine-focus sealed tube	5369 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→13
T_min = 0.636, T_max = 0.746	k = −16→16
13040 measured reflections	l = −16→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0689P)² + 0.6349P] where P = (F_o² + 2F_c²)/3
6303 reflections	(Δ/σ)_max = 0.001
347 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₆H₃₀O₉S₃	γ = 68.085 (2)°
M_r = 582.68	V = 1379.32 (7) Å³
Triclinic, P1	Z = 2
a = 10.2055 (3) Å	Mo Kα radiation
b = 12.4029 (3) Å	µ = 0.32 mm⁻¹
c = 12.7993 (4) Å	T = 100 K
α = 66.868 (2)°	0.30 × 0.28 × 0.28 mm
β = 78.370 (2)°

Data collection top

Bruker SMART APEX diffractometer	6305 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5369 reflections with I > 2σ(I)
T_min = 0.636, T_max = 0.746	R_int = 0.031
13040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 0.99	Δρ_max = 0.44 e Å⁻³
6303 reflections	Δρ_min = −0.45 e Å⁻³
347 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.58792 (4)	0.97996 (4)	0.76513 (3)	0.01532 (11)
S2	0.63629 (5)	0.55361 (4)	1.15173 (4)	0.01764 (12)
S3	0.03815 (4)	0.75579 (4)	1.20789 (4)	0.01627 (11)
O1	0.52171 (13)	0.87644 (11)	0.84519 (10)	0.0162 (3)
O2	0.61934 (13)	1.03502 (12)	0.83218 (11)	0.0202 (3)
O3	0.69823 (13)	0.91966 (12)	0.69899 (11)	0.0214 (3)
O4	0.49589 (13)	0.66725 (11)	1.11596 (10)	0.0164 (3)
O5	0.61861 (14)	0.44646 (11)	1.14753 (11)	0.0221 (3)
O6	0.66462 (15)	0.55276 (12)	1.25683 (11)	0.0247 (3)
O7	0.16219 (13)	0.74483 (11)	1.11229 (11)	0.0173 (3)
O8	−0.07307 (13)	0.87019 (12)	1.16416 (11)	0.0217 (3)
O9	0.01154 (14)	0.64130 (12)	1.24502 (11)	0.0221 (3)
C1	0.33373 (18)	0.81398 (15)	0.97005 (14)	0.0148 (3)
C2	0.41265 (18)	0.90728 (15)	0.93184 (14)	0.0156 (3)
H2A	0.3469	0.9927	0.8998	0.019*
H2B	0.4563	0.9016	0.9971	0.019*
C3	0.43504 (18)	0.68148 (15)	1.01508 (14)	0.0152 (3)
H3A	0.3835	0.6216	1.0353	0.018*
H3B	0.5111	0.6653	0.9561	0.018*
C4	0.22335 (18)	0.84493 (15)	1.06289 (15)	0.0166 (3)
H4A	0.2681	0.8502	1.1218	0.020*
H4B	0.1492	0.9254	1.0302	0.020*
C5	0.26204 (19)	0.82440 (16)	0.87058 (15)	0.0190 (4)
H5A	0.2030	0.7707	0.8988	0.029*
H5B	0.3345	0.7986	0.8141	0.029*
H5C	0.2028	0.9106	0.8352	0.029*
C6	0.45022 (18)	1.08899 (16)	0.67862 (14)	0.0156 (3)
C7	0.39715 (19)	1.21074 (16)	0.67582 (15)	0.0190 (4)
H7	0.4322	1.2353	0.7232	0.023*
C8	0.2920 (2)	1.29600 (17)	0.60257 (16)	0.0214 (4)
H8	0.2547	1.3793	0.6004	0.026*
C9	0.2403 (2)	1.26130 (17)	0.53222 (15)	0.0210 (4)
C10	0.2951 (2)	1.13761 (17)	0.53788 (15)	0.0214 (4)
H10	0.2598	1.1125	0.4911	0.026*
C11	0.39924 (19)	1.05159 (17)	0.61026 (15)	0.0196 (4)
H11	0.4357	0.9679	0.6134	0.023*
C12	0.1290 (2)	1.3539 (2)	0.45091 (18)	0.0309 (5)
H12A	0.1033	1.4355	0.4576	0.046*
H12B	0.0451	1.3277	0.4692	0.046*
H12C	0.1660	1.3590	0.3729	0.046*
C13	0.75954 (18)	0.59940 (16)	1.04278 (15)	0.0182 (4)
C14	0.81123 (19)	0.54084 (16)	0.96273 (16)	0.0201 (4)
H14	0.7862	0.4714	0.9707	0.024*
C15	0.89955 (19)	0.58496 (18)	0.87131 (17)	0.0229 (4)
H15	0.9366	0.5443	0.8172	0.027*
C16	0.93463 (19)	0.68791 (18)	0.85776 (17)	0.0237 (4)
C17	0.8845 (2)	0.74337 (18)	0.94043 (18)	0.0246 (4)
H17	0.9105	0.8122	0.9330	0.030*
C18	0.79780 (19)	0.69997 (17)	1.03297 (17)	0.0214 (4)
H18	0.7647	0.7381	1.0891	0.026*
C19	1.0234 (2)	0.7391 (2)	0.75402 (19)	0.0309 (5)
H19A	1.0906	0.6711	0.7302	0.046*
H19B	1.0755	0.7811	0.7722	0.046*
H19C	0.9620	0.7984	0.6921	0.046*
C20	0.11684 (19)	0.76273 (16)	1.31382 (15)	0.0178 (3)
C21	0.2287 (2)	0.66056 (18)	1.36842 (18)	0.0257 (4)
H21	0.2603	0.5876	1.3496	0.031*
C22	0.2925 (2)	0.66671 (19)	1.44988 (18)	0.0292 (4)
H22	0.3678	0.5967	1.4880	0.035*
C23	0.2490 (2)	0.77374 (19)	1.47790 (16)	0.0250 (4)
C24	0.1370 (2)	0.87365 (18)	1.42254 (16)	0.0251 (4)
H24	0.1051	0.9467	1.4412	0.030*
C25	0.0706 (2)	0.86935 (17)	1.34066 (16)	0.0227 (4)
H25	−0.0058	0.9387	1.3034	0.027*
C26	0.3242 (2)	0.7802 (2)	1.56393 (17)	0.0331 (5)
H26A	0.4148	0.7925	1.5292	0.050*
H26B	0.3415	0.7027	1.6296	0.050*
H26C	0.2655	0.8497	1.5890	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0169 (2)	0.0172 (2)	0.0134 (2)	−0.00673 (16)	−0.00021 (15)	−0.00623 (16)
S2	0.0226 (2)	0.0123 (2)	0.0173 (2)	−0.00169 (16)	−0.00767 (17)	−0.00503 (16)
S3	0.0153 (2)	0.0155 (2)	0.0178 (2)	−0.00525 (16)	−0.00088 (16)	−0.00542 (17)
O1	0.0194 (6)	0.0150 (6)	0.0148 (6)	−0.0057 (5)	0.0015 (5)	−0.0069 (5)
O2	0.0243 (7)	0.0240 (6)	0.0186 (6)	−0.0125 (5)	−0.0027 (5)	−0.0090 (5)
O3	0.0184 (6)	0.0251 (7)	0.0196 (6)	−0.0054 (5)	0.0018 (5)	−0.0098 (5)
O4	0.0190 (6)	0.0138 (6)	0.0157 (6)	−0.0016 (5)	−0.0058 (5)	−0.0058 (5)
O5	0.0288 (7)	0.0132 (6)	0.0244 (7)	−0.0042 (5)	−0.0077 (5)	−0.0061 (5)
O6	0.0349 (8)	0.0193 (6)	0.0192 (7)	−0.0033 (6)	−0.0123 (6)	−0.0060 (5)
O7	0.0179 (6)	0.0159 (6)	0.0202 (6)	−0.0077 (5)	0.0019 (5)	−0.0079 (5)
O8	0.0169 (6)	0.0211 (6)	0.0242 (7)	−0.0027 (5)	−0.0027 (5)	−0.0075 (5)
O9	0.0234 (7)	0.0213 (6)	0.0241 (7)	−0.0117 (5)	0.0004 (5)	−0.0074 (5)
C1	0.0162 (8)	0.0133 (7)	0.0151 (8)	−0.0041 (6)	−0.0025 (6)	−0.0051 (6)
C2	0.0184 (8)	0.0151 (8)	0.0130 (8)	−0.0051 (6)	0.0018 (6)	−0.0064 (6)
C3	0.0184 (8)	0.0138 (7)	0.0151 (8)	−0.0040 (6)	−0.0048 (6)	−0.0062 (6)
C4	0.0175 (8)	0.0131 (8)	0.0198 (8)	−0.0066 (6)	0.0008 (7)	−0.0059 (7)
C5	0.0207 (9)	0.0169 (8)	0.0203 (9)	−0.0030 (7)	−0.0063 (7)	−0.0079 (7)
C6	0.0178 (8)	0.0175 (8)	0.0115 (8)	−0.0066 (6)	0.0007 (6)	−0.0052 (6)
C7	0.0247 (9)	0.0187 (8)	0.0164 (8)	−0.0093 (7)	0.0011 (7)	−0.0080 (7)
C8	0.0257 (9)	0.0166 (8)	0.0199 (9)	−0.0063 (7)	0.0015 (7)	−0.0064 (7)
C9	0.0227 (9)	0.0218 (9)	0.0147 (8)	−0.0082 (7)	0.0000 (7)	−0.0024 (7)
C10	0.0244 (9)	0.0269 (9)	0.0162 (8)	−0.0097 (8)	−0.0025 (7)	−0.0091 (7)
C11	0.0233 (9)	0.0192 (8)	0.0177 (9)	−0.0071 (7)	−0.0003 (7)	−0.0085 (7)
C12	0.0318 (11)	0.0291 (10)	0.0245 (10)	−0.0062 (9)	−0.0080 (8)	−0.0027 (8)
C13	0.0177 (8)	0.0160 (8)	0.0208 (9)	−0.0013 (6)	−0.0073 (7)	−0.0075 (7)
C14	0.0192 (9)	0.0175 (8)	0.0238 (9)	−0.0007 (7)	−0.0091 (7)	−0.0086 (7)
C15	0.0184 (9)	0.0250 (9)	0.0245 (10)	0.0003 (7)	−0.0087 (7)	−0.0114 (8)
C16	0.0154 (8)	0.0261 (9)	0.0263 (10)	−0.0017 (7)	−0.0082 (7)	−0.0074 (8)
C17	0.0196 (9)	0.0226 (9)	0.0342 (11)	−0.0055 (7)	−0.0082 (8)	−0.0107 (8)
C18	0.0188 (9)	0.0200 (9)	0.0284 (10)	−0.0027 (7)	−0.0071 (7)	−0.0123 (8)
C19	0.0193 (10)	0.0401 (12)	0.0323 (11)	−0.0104 (9)	−0.0014 (8)	−0.0111 (10)
C20	0.0203 (8)	0.0187 (8)	0.0160 (8)	−0.0089 (7)	0.0004 (7)	−0.0061 (7)
C21	0.0262 (10)	0.0205 (9)	0.0292 (10)	−0.0035 (8)	−0.0086 (8)	−0.0083 (8)
C22	0.0301 (11)	0.0258 (10)	0.0287 (11)	−0.0073 (8)	−0.0119 (8)	−0.0035 (8)
C23	0.0305 (10)	0.0334 (10)	0.0164 (9)	−0.0207 (9)	0.0029 (8)	−0.0066 (8)
C24	0.0321 (10)	0.0264 (10)	0.0211 (9)	−0.0141 (8)	0.0050 (8)	−0.0118 (8)
C25	0.0253 (9)	0.0205 (9)	0.0214 (9)	−0.0074 (7)	0.0014 (7)	−0.0077 (7)
C26	0.0409 (12)	0.0497 (13)	0.0188 (10)	−0.0300 (11)	0.0008 (9)	−0.0092 (9)

Geometric parameters (Å, º) top

S1—O3	1.4241 (13)	C9—C12	1.502 (3)
S1—O2	1.4284 (13)	C10—C11	1.379 (3)
S1—O1	1.5780 (12)	C10—H10	0.9500
S1—C6	1.7498 (18)	C11—H11	0.9500
S2—O5	1.4286 (13)	C12—H12A	0.9800
S2—O6	1.4270 (13)	C12—H12B	0.9800
S2—O4	1.5809 (12)	C12—H12C	0.9800
S2—C13	1.7473 (19)	C13—C14	1.392 (2)
S3—O9	1.4219 (13)	C13—C18	1.395 (2)
S3—O8	1.4299 (13)	C14—C15	1.386 (3)
S3—O7	1.5799 (12)	C14—H14	0.9500
S3—C20	1.7530 (18)	C15—C16	1.389 (3)
O1—C2	1.4605 (19)	C15—H15	0.9500
O4—C3	1.4650 (19)	C16—C17	1.395 (3)
O7—C4	1.4606 (19)	C16—C19	1.507 (3)
C1—C2	1.523 (2)	C17—C18	1.381 (3)
C1—C4	1.525 (2)	C17—H17	0.9500
C1—C3	1.526 (2)	C18—H18	0.9500
C1—C5	1.533 (2)	C19—H19A	0.9800
C2—H2A	0.9900	C19—H19B	0.9800
C2—H2B	0.9900	C19—H19C	0.9800
C3—H3A	0.9900	C20—C25	1.384 (2)
C3—H3B	0.9900	C20—C21	1.394 (3)
C4—H4A	0.9900	C21—C22	1.375 (3)
C4—H4B	0.9900	C21—H21	0.9500
C5—H5A	0.9800	C22—C23	1.399 (3)
C5—H5B	0.9800	C22—H22	0.9500
C5—H5C	0.9800	C23—C24	1.387 (3)
C6—C11	1.391 (2)	C23—C26	1.505 (3)
C6—C7	1.389 (2)	C24—C25	1.385 (3)
C7—C8	1.389 (3)	C24—H24	0.9500
C7—H7	0.9500	C25—H25	0.9500
C8—C9	1.393 (3)	C26—H26A	0.9800
C8—H8	0.9500	C26—H26B	0.9800
C9—C10	1.400 (3)	C26—H26C	0.9800

O3—S1—O2	120.03 (8)	C10—C9—C12	120.15 (18)
O3—S1—O1	104.03 (7)	C11—C10—C9	121.12 (17)
O2—S1—O1	109.40 (7)	C11—C10—H10	119.4
O3—S1—C6	109.49 (8)	C9—C10—H10	119.4
O2—S1—C6	109.38 (8)	C10—C11—C6	119.11 (16)
O1—S1—C6	103.10 (7)	C10—C11—H11	120.4
O5—S2—O6	119.61 (8)	C6—C11—H11	120.4
O5—S2—O4	108.93 (7)	C9—C12—H12A	109.5
O6—S2—O4	104.27 (7)	C9—C12—H12B	109.5
O5—S2—C13	109.07 (8)	H12A—C12—H12B	109.5
O6—S2—C13	111.07 (9)	C9—C12—H12C	109.5
O4—S2—C13	102.39 (7)	H12A—C12—H12C	109.5
O9—S3—O8	119.98 (8)	H12B—C12—H12C	109.5
O9—S3—O7	104.01 (7)	C14—C13—C18	120.74 (18)
O8—S3—O7	108.91 (7)	C14—C13—S2	119.90 (14)
O9—S3—C20	110.37 (8)	C18—C13—S2	119.23 (14)
O8—S3—C20	109.18 (8)	C13—C14—C15	119.28 (17)
O7—S3—C20	102.94 (8)	C13—C14—H14	120.4
C2—O1—S1	117.04 (10)	C15—C14—H14	120.4
C3—O4—S2	115.37 (10)	C14—C15—C16	120.83 (18)
C4—O7—S3	117.67 (10)	C14—C15—H15	119.6
C2—C1—C4	106.13 (13)	C16—C15—H15	119.6
C2—C1—C3	110.89 (14)	C15—C16—C17	118.95 (19)
C4—C1—C3	111.03 (14)	C15—C16—C19	119.98 (18)
C2—C1—C5	110.90 (14)	C17—C16—C19	121.06 (19)
C4—C1—C5	110.44 (14)	C18—C17—C16	121.14 (18)
C3—C1—C5	107.49 (13)	C18—C17—H17	119.4
O1—C2—C1	106.76 (13)	C16—C17—H17	119.4
O1—C2—H2A	110.4	C17—C18—C13	118.99 (17)
C1—C2—H2A	110.4	C17—C18—H18	120.5
O1—C2—H2B	110.4	C13—C18—H18	120.5
C1—C2—H2B	110.4	C16—C19—H19A	109.5
H2A—C2—H2B	108.6	C16—C19—H19B	109.5
O4—C3—C1	108.11 (12)	H19A—C19—H19B	109.5
O4—C3—H3A	110.1	C16—C19—H19C	109.5
C1—C3—H3A	110.1	H19A—C19—H19C	109.5
O4—C3—H3B	110.1	H19B—C19—H19C	109.5
C1—C3—H3B	110.1	C25—C20—C21	120.65 (18)
H3A—C3—H3B	108.4	C25—C20—S3	120.30 (15)
O7—C4—C1	106.51 (13)	C21—C20—S3	119.03 (14)
O7—C4—H4A	110.4	C22—C21—C20	119.15 (18)
C1—C4—H4A	110.4	C22—C21—H21	120.4
O7—C4—H4B	110.4	C20—C21—H21	120.4
C1—C4—H4B	110.4	C21—C22—C23	121.48 (19)
H4A—C4—H4B	108.6	C21—C22—H22	119.3
C1—C5—H5A	109.5	C23—C22—H22	119.3
C1—C5—H5B	109.5	C24—C23—C22	118.02 (18)
H5A—C5—H5B	109.5	C24—C23—C26	121.39 (19)
C1—C5—H5C	109.5	C22—C23—C26	120.57 (19)
H5A—C5—H5C	109.5	C25—C24—C23	121.51 (17)
H5B—C5—H5C	109.5	C25—C24—H24	119.2
C11—C6—C7	121.17 (17)	C23—C24—H24	119.2
C11—C6—S1	118.32 (13)	C24—C25—C20	119.18 (18)
C7—C6—S1	120.47 (14)	C24—C25—H25	120.4
C6—C7—C8	118.89 (17)	C20—C25—H25	120.4
C6—C7—H7	120.6	C23—C26—H26A	109.5
C8—C7—H7	120.6	C23—C26—H26B	109.5
C9—C8—C7	121.08 (16)	H26A—C26—H26B	109.5
C9—C8—H8	119.5	C23—C26—H26C	109.5
C7—C8—H8	119.5	H26A—C26—H26C	109.5
C8—C9—C10	118.62 (17)	H26B—C26—H26C	109.5
C8—C9—C12	121.23 (17)

O3—S1—O1—C2	174.43 (11)	C7—C6—C11—C10	0.6 (3)
O2—S1—O1—C2	45.02 (13)	S1—C6—C11—C10	−177.19 (13)
C6—S1—O1—C2	−71.29 (13)	O5—S2—C13—C14	6.56 (17)
O5—S2—O4—C3	−45.30 (13)	O6—S2—C13—C14	140.46 (14)
O6—S2—O4—C3	−174.07 (11)	O4—S2—C13—C14	−108.75 (15)
C13—S2—O4—C3	70.11 (12)	O5—S2—C13—C18	−177.62 (14)
O9—S3—O7—C4	−174.81 (12)	O6—S2—C13—C18	−43.72 (16)
O8—S3—O7—C4	56.15 (13)	O4—S2—C13—C18	67.08 (15)
C20—S3—O7—C4	−59.63 (13)	C18—C13—C14—C15	−1.2 (3)
S1—O1—C2—C1	161.94 (11)	S2—C13—C14—C15	174.54 (13)
C4—C1—C2—O1	178.34 (13)	C13—C14—C15—C16	−1.2 (3)
C3—C1—C2—O1	57.66 (17)	C14—C15—C16—C17	2.8 (3)
C5—C1—C2—O1	−61.69 (17)	C14—C15—C16—C19	−176.23 (17)
S2—O4—C3—C1	−161.46 (11)	C15—C16—C17—C18	−2.0 (3)
C2—C1—C3—O4	63.10 (17)	C19—C16—C17—C18	177.03 (17)
C4—C1—C3—O4	−54.63 (18)	C16—C17—C18—C13	−0.4 (3)
C5—C1—C3—O4	−175.53 (13)	C14—C13—C18—C17	2.0 (3)
S3—O7—C4—C1	−177.15 (11)	S2—C13—C18—C17	−173.78 (14)
C2—C1—C4—O7	−171.40 (13)	O9—S3—C20—C25	−135.36 (15)
C3—C1—C4—O7	−50.81 (18)	O8—S3—C20—C25	−1.46 (18)
C5—C1—C4—O7	68.33 (17)	O7—S3—C20—C25	114.13 (15)
O3—S1—C6—C11	49.51 (16)	O9—S3—C20—C21	46.18 (17)
O2—S1—C6—C11	−177.08 (13)	O8—S3—C20—C21	−179.91 (14)
O1—S1—C6—C11	−60.76 (15)	O7—S3—C20—C21	−64.32 (16)
O3—S1—C6—C7	−128.28 (14)	C25—C20—C21—C22	0.2 (3)
O2—S1—C6—C7	5.13 (17)	S3—C20—C21—C22	178.66 (16)
O1—S1—C6—C7	121.45 (14)	C20—C21—C22—C23	−0.9 (3)
C11—C6—C7—C8	−0.4 (3)	C21—C22—C23—C24	1.2 (3)
S1—C6—C7—C8	177.30 (13)	C21—C22—C23—C26	−177.53 (19)
C6—C7—C8—C9	−0.4 (3)	C22—C23—C24—C25	−0.9 (3)
C7—C8—C9—C10	1.0 (3)	C26—C23—C24—C25	177.89 (18)
C7—C8—C9—C12	−178.54 (17)	C23—C24—C25—C20	0.2 (3)
C8—C9—C10—C11	−0.8 (3)	C21—C20—C25—C24	0.1 (3)
C12—C9—C10—C11	178.70 (17)	S3—C20—C25—C24	−178.28 (14)
C9—C10—C11—C6	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2b···O2ⁱ	0.99	2.49	3.297 (2)	138
C4—H4a···O2ⁱ	0.99	2.42	3.290 (2)	147
C5—H5c···O8ⁱⁱ	0.98	2.54	3.440 (2)	152
C7—H7···O6ⁱ	0.95	2.54	3.183 (2)	125
C10—H10···O3ⁱⁱⁱ	0.95	2.54	3.358 (2)	144
C15—H15···O9^iv	0.95	2.56	3.428 (3)	151

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

Experimental details

Crystal data
Chemical formula	C₂₆H₃₀O₉S₃
M_r	582.68
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.2055 (3), 12.4029 (3), 12.7993 (4)
α, β, γ (°)	66.868 (2), 78.370 (2), 68.085 (2)
V (Å³)	1379.32 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.30 × 0.28 × 0.28

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.636, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13040, 6305, 5369
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.117, 0.99
No. of reflections	6303
No. of parameters	347
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.45

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C2—H2b···O2ⁱ	0.99	2.49	3.297 (2)	138
C4—H4a···O2ⁱ	0.99	2.42	3.290 (2)	147
C5—H5c···O8ⁱⁱ	0.98	2.54	3.440 (2)	152
C7—H7···O6ⁱ	0.95	2.54	3.183 (2)	125
C10—H10···O3ⁱⁱⁱ	0.95	2.54	3.358 (2)	144
C15—H15···O9^iv	0.95	2.56	3.428 (3)	151

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

Footnotes

‡Additional correspondence author, e-mail: yatimah70@um.edu.my.

Acknowledgements

The University of Malaya is thanked for support of this research through a research grant (FRGS FP001/2010 A) and for the maintenance of the crystallographic facility.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fujihara, T., Shioji, E. & Nagasawa, A. (2007). Acta Cryst. E63, o3628. Web of Science CSD CrossRef IUCr Journals Google Scholar
Laliberte, D., Maris, T., Sirois, A. & Wuest, J. D. (2003). Org. Lett. 5, 4787–4790. Web of Science PubMed CAS Google Scholar
Li, S.-X., Li, H.-M., Lu, Z.-L., Fun, H.-K. & Chantrapromma, S. (2008a). Acta Cryst. E64, o1472–o1473. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, S.-X., Zhu, L., Fun, H.-K. & Chantrapromma, S. (2008b). Acta Cryst. E64, o1474–o1475. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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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doi:10.1107/S1600536811024664

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2-Methyl-3-[(4-methyl­phen­yl)sulfon­yl­­oxy]-2-{[(4-methyl­phen­yl)sulfon­yl­oxy]meth­yl}propyl 4-methyl­benzene­sulfonate

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Experimental

Crystal data

Data collection

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Supporting information

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Acknowledgements

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organic compounds

2-Methyl-3-[(4-methylphenyl)sulfonyloxy]-2-{[(4-methylphenyl)sulfonyloxy]methyl}propyl 4-methylbenzenesulfonate