1-(4-Methyl­phen­yl)-2-(phenyl­sulfon­yl)ethanone

Abdel-Aziz, H.A.; Al-Rashood, K.A.; Ghabbour, H.A.; Fun, H.-K.; Chia, T.S.

doi:10.1107/S160053681200966X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1033

doi:10.1107/S160053681200966X

Open

access

1-(4-Methylphenyl)-2-(phenylsulfonyl)ethanone

Hatem A. Abdel-Aziz,^a Khalid A. Al-Rashood,^a Hazem A. Ghabbour,^a Hoong-Kun Fun ^b ^*‡ and Tze Shyang Chia ^b

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 5 March 2012; accepted 5 March 2012; online 10 March 2012)

In the title compound, C₁₅H₁₄O₃S, the benzene and phenyl rings make a dihedral angle of 33.56 (16)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into a layer parallel to the ab plane.

Related literature

For background to the chemistry of sulfones, see: Xiang et al. (2007 ); Abdel-Aziz & Mekawey (2009 ); Abdel-Aziz et al. (2010 ). For a related structure, see: Abdel-Aziz et al. (2011 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄O₃S
M_r = 274.32
Orthorhombic, P b c a
a = 11.5555 (12) Å
b = 10.1981 (11) Å
c = 22.843 (2) Å
V = 2692.0 (5) Å³
Z = 8
Cu Kα radiation
μ = 2.15 mm⁻¹
T = 296 K
0.55 × 0.12 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.386, T_max = 0.919
10168 measured reflections
2487 independent reflections
1446 reflections with I > 2σ(I)
R_int = 0.068

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 0.89
2487 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1ⁱ	0.97	2.42	3.366 (3)	164
C10—H10A⋯O3ⁱⁱ	0.93	2.48	3.342 (4)	154
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681200966X/is5087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200966X/is5087Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681200966X/is5087Isup3.cml

checkCIF report

Comment top

In the title compound (Fig. 1), the two aromatic rings (C1–C6 and C9–C14) form a dihedral angle of 33.56 (16)° with each other. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structure (Abdel-Aziz et al., 2011). In the crystal packing (Fig. 2), the molecules are linked by intermolecular C7—H7B···O1 and C10—H10A···O3 hydrogen bonds (Table 1) into two-dimensional networks parallel to the ab plane.

Related literature top

For background to the chemistry of sulfones, see: Xiang et al. (2007); Abdel-Aziz & Mekawey (2009); Abdel-Aziz et al. (2010). For a related structure, see: Abdel-Aziz et al. (2011). For reference bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the reported method (Xiang et al., 2007). Single crystals of the title compound were obtained by slow evaporation from an ethanol solution at room temperature.

Structure description top

For background to the chemistry of sulfones, see: Xiang et al. (2007); Abdel-Aziz & Mekawey (2009); Abdel-Aziz et al. (2010). For a related structure, see: Abdel-Aziz et al. (2011). For reference bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For clarity sake, hydrogen atoms not involved in hydrogen bonding have been omitted.

1-(4-Methylphenyl)-2-(phenylsulfonyl)ethanone top

Crystal data top

C₁₅H₁₄O₃S	F(000) = 1152
M_r = 274.32	D_x = 1.354 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 484 reflections
a = 11.5555 (12) Å	θ = 3.9–33.7°
b = 10.1981 (11) Å	µ = 2.15 mm⁻¹
c = 22.843 (2) Å	T = 296 K
V = 2692.0 (5) Å³	Needle, colourless
Z = 8	0.55 × 0.12 × 0.04 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2487 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
φ and ω scans	θ_max = 70.0°, θ_min = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→14
T_min = 0.386, T_max = 0.919	k = −9→11
10168 measured reflections	l = −27→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0623P)²] where P = (F_o² + 2F_c²)/3
S = 0.89	(Δ/σ)_max < 0.001
2487 reflections	Δρ_max = 0.19 e Å⁻³
174 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00131 (15)

Crystal data top

C₁₅H₁₄O₃S	V = 2692.0 (5) Å³
M_r = 274.32	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 11.5555 (12) Å	µ = 2.15 mm⁻¹
b = 10.1981 (11) Å	T = 296 K
c = 22.843 (2) Å	0.55 × 0.12 × 0.04 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2487 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1446 reflections with I > 2σ(I)
T_min = 0.386, T_max = 0.919	R_int = 0.068
10168 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 0.89	Δρ_max = 0.19 e Å⁻³
2487 reflections	Δρ_min = −0.25 e Å⁻³
174 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.69612 (6)	0.25970 (7)	0.35841 (3)	0.0496 (2)
O1	0.67330 (18)	0.12398 (18)	0.34807 (10)	0.0602 (6)
O2	0.60372 (18)	0.3428 (2)	0.37858 (10)	0.0666 (6)
O3	0.94161 (18)	0.2723 (2)	0.27397 (11)	0.0727 (7)
C1	0.8099 (2)	0.2698 (3)	0.40947 (13)	0.0498 (7)
C2	0.8117 (3)	0.3717 (3)	0.44912 (14)	0.0652 (9)
H2A	0.7562	0.4377	0.4476	0.078*
C3	0.8977 (3)	0.3739 (4)	0.49129 (15)	0.0791 (11)
H3A	0.8998	0.4410	0.5188	0.095*
C4	0.9795 (4)	0.2774 (4)	0.49242 (17)	0.0835 (12)
H4A	1.0372	0.2799	0.5208	0.100*
C5	0.9782 (3)	0.1777 (4)	0.45296 (17)	0.0797 (11)
H5A	1.0354	0.1135	0.4542	0.096*
C6	0.8919 (3)	0.1715 (3)	0.41090 (14)	0.0636 (8)
H6A	0.8894	0.1026	0.3842	0.076*
C7	0.7484 (3)	0.3314 (3)	0.29256 (12)	0.0513 (7)
H7A	0.6841	0.3433	0.2658	0.062*
H7B	0.7799	0.4174	0.3013	0.062*
C8	0.8414 (2)	0.2493 (3)	0.26254 (12)	0.0503 (7)
C9	0.8077 (2)	0.1467 (3)	0.22005 (12)	0.0459 (6)
C10	0.6939 (2)	0.1183 (3)	0.20632 (13)	0.0520 (7)
H10A	0.6344	0.1646	0.2243	0.062*
C11	0.6681 (3)	0.0219 (3)	0.16615 (13)	0.0575 (8)
H11A	0.5910	0.0031	0.1580	0.069*
C12	0.7533 (3)	−0.0470 (3)	0.13781 (13)	0.0559 (7)
C13	0.8667 (3)	−0.0200 (3)	0.15236 (14)	0.0576 (8)
H13A	0.9258	−0.0669	0.1344	0.069*
C14	0.8942 (2)	0.0743 (3)	0.19262 (13)	0.0549 (7)
H14A	0.9714	0.0902	0.2017	0.066*
C15	0.7230 (3)	−0.1491 (3)	0.09252 (15)	0.0753 (10)
H15B	0.6483	−0.1854	0.1012	0.113*
H15C	0.7799	−0.2176	0.0931	0.113*
H15A	0.7214	−0.1093	0.0545	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0458 (4)	0.0490 (4)	0.0540 (4)	−0.0012 (3)	0.0010 (3)	−0.0013 (3)
O1	0.0659 (14)	0.0448 (12)	0.0700 (14)	−0.0143 (9)	−0.0041 (11)	−0.0014 (10)
O2	0.0541 (13)	0.0746 (16)	0.0710 (15)	0.0124 (10)	0.0071 (11)	−0.0079 (11)
O3	0.0480 (13)	0.0813 (17)	0.0887 (17)	−0.0041 (11)	−0.0105 (12)	−0.0201 (13)
C1	0.0506 (17)	0.0480 (17)	0.0509 (15)	−0.0049 (13)	0.0002 (13)	0.0035 (12)
C2	0.078 (2)	0.057 (2)	0.0599 (19)	−0.0065 (16)	−0.0027 (18)	−0.0040 (15)
C3	0.093 (3)	0.084 (3)	0.061 (2)	−0.024 (2)	−0.007 (2)	−0.0066 (19)
C4	0.074 (3)	0.114 (4)	0.062 (2)	−0.018 (2)	−0.0189 (19)	0.023 (2)
C5	0.067 (2)	0.094 (3)	0.078 (3)	0.006 (2)	−0.007 (2)	0.018 (2)
C6	0.0573 (19)	0.065 (2)	0.068 (2)	0.0057 (15)	−0.0047 (17)	0.0045 (16)
C7	0.0611 (18)	0.0432 (17)	0.0495 (16)	0.0030 (13)	−0.0005 (14)	0.0020 (12)
C8	0.0482 (17)	0.0517 (17)	0.0508 (16)	0.0008 (13)	−0.0023 (13)	0.0039 (13)
C9	0.0421 (15)	0.0466 (16)	0.0491 (15)	0.0022 (11)	0.0002 (13)	0.0034 (12)
C10	0.0408 (15)	0.0613 (18)	0.0540 (17)	0.0053 (13)	0.0030 (14)	0.0020 (13)
C11	0.0465 (18)	0.066 (2)	0.0599 (18)	−0.0071 (14)	−0.0064 (15)	0.0013 (15)
C12	0.0628 (19)	0.0579 (18)	0.0471 (15)	−0.0022 (14)	−0.0031 (16)	0.0031 (14)
C13	0.0544 (19)	0.0594 (19)	0.0590 (18)	0.0086 (13)	0.0040 (16)	−0.0045 (15)
C14	0.0412 (16)	0.0636 (19)	0.0599 (18)	0.0035 (13)	−0.0013 (14)	−0.0034 (14)
C15	0.093 (3)	0.071 (2)	0.061 (2)	−0.0040 (18)	−0.0110 (19)	−0.0085 (17)

Geometric parameters (Å, º) top

S1—O1	1.4287 (19)	C7—H7A	0.9700
S1—O2	1.439 (2)	C7—H7B	0.9700
S1—C1	1.760 (3)	C8—C9	1.480 (4)
S1—C7	1.778 (3)	C9—C10	1.382 (4)
O3—C8	1.210 (3)	C9—C14	1.391 (4)
C1—C2	1.379 (4)	C10—C11	1.377 (4)
C1—C6	1.380 (4)	C10—H10A	0.9300
C2—C3	1.385 (4)	C11—C12	1.373 (4)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.364 (5)	C12—C13	1.379 (4)
C3—H3A	0.9300	C12—C15	1.509 (4)
C4—C5	1.359 (5)	C13—C14	1.368 (4)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.386 (5)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15B	0.9600
C6—H6A	0.9300	C15—H15C	0.9600
C7—C8	1.525 (4)	C15—H15A	0.9600

O1—S1—O2	119.10 (13)	H7A—C7—H7B	107.7
O1—S1—C1	107.69 (13)	O3—C8—C9	122.0 (3)
O2—S1—C1	107.92 (14)	O3—C8—C7	118.1 (3)
O1—S1—C7	108.74 (14)	C9—C8—C7	119.9 (2)
O2—S1—C7	106.32 (14)	C10—C9—C14	118.0 (3)
C1—S1—C7	106.42 (14)	C10—C9—C8	123.2 (3)
C2—C1—C6	121.4 (3)	C14—C9—C8	118.8 (3)
C2—C1—S1	119.4 (2)	C11—C10—C9	120.4 (3)
C6—C1—S1	119.1 (2)	C11—C10—H10A	119.8
C1—C2—C3	118.7 (3)	C9—C10—H10A	119.8
C1—C2—H2A	120.7	C12—C11—C10	121.6 (3)
C3—C2—H2A	120.7	C12—C11—H11A	119.2
C4—C3—C2	119.9 (4)	C10—C11—H11A	119.2
C4—C3—H3A	120.0	C11—C12—C13	117.7 (3)
C2—C3—H3A	120.0	C11—C12—C15	120.7 (3)
C5—C4—C3	121.3 (4)	C13—C12—C15	121.6 (3)
C5—C4—H4A	119.3	C14—C13—C12	121.5 (3)
C3—C4—H4A	119.3	C14—C13—H13A	119.2
C4—C5—C6	120.1 (4)	C12—C13—H13A	119.2
C4—C5—H5A	120.0	C13—C14—C9	120.6 (3)
C6—C5—H5A	120.0	C13—C14—H14A	119.7
C1—C6—C5	118.5 (3)	C9—C14—H14A	119.7
C1—C6—H6A	120.7	C12—C15—H15B	109.5
C5—C6—H6A	120.7	C12—C15—H15C	109.5
C8—C7—S1	113.21 (19)	H15B—C15—H15C	109.5
C8—C7—H7A	108.9	C12—C15—H15A	109.5
S1—C7—H7A	108.9	H15B—C15—H15A	109.5
C8—C7—H7B	108.9	H15C—C15—H15A	109.5
S1—C7—H7B	108.9

O1—S1—C1—C2	−146.6 (2)	S1—C7—C8—O3	−92.6 (3)
O2—S1—C1—C2	−16.8 (3)	S1—C7—C8—C9	88.4 (3)
C7—S1—C1—C2	97.0 (3)	O3—C8—C9—C10	179.8 (3)
O1—S1—C1—C6	30.0 (3)	C7—C8—C9—C10	−1.2 (4)
O2—S1—C1—C6	159.8 (2)	O3—C8—C9—C14	0.2 (4)
C7—S1—C1—C6	−86.4 (3)	C7—C8—C9—C14	179.1 (3)
C6—C1—C2—C3	−0.4 (5)	C14—C9—C10—C11	−0.6 (4)
S1—C1—C2—C3	176.1 (2)	C8—C9—C10—C11	179.7 (3)
C1—C2—C3—C4	1.0 (5)	C9—C10—C11—C12	−1.2 (5)
C2—C3—C4—C5	−0.4 (6)	C10—C11—C12—C13	2.3 (5)
C3—C4—C5—C6	−0.8 (6)	C10—C11—C12—C15	−178.0 (3)
C2—C1—C6—C5	−0.8 (5)	C11—C12—C13—C14	−1.5 (5)
S1—C1—C6—C5	−177.3 (3)	C15—C12—C13—C14	178.7 (3)
C4—C5—C6—C1	1.4 (5)	C12—C13—C14—C9	−0.3 (5)
O1—S1—C7—C8	−46.2 (3)	C10—C9—C14—C13	1.4 (4)
O2—S1—C7—C8	−175.5 (2)	C8—C9—C14—C13	−178.9 (3)
C1—S1—C7—C8	69.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1ⁱ	0.97	2.42	3.366 (3)	164
C10—H10A···O3ⁱⁱ	0.93	2.48	3.342 (4)	154

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄O₃S
M_r	274.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	11.5555 (12), 10.1981 (11), 22.843 (2)
V (Å³)	2692.0 (5)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.55 × 0.12 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.386, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	10168, 2487, 1446
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 0.89
No. of reflections	2487
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.25

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1ⁱ	0.97	2.42	3.366 (3)	164
C10—H10A···O3ⁱⁱ	0.93	2.48	3.342 (4)	154

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1/2, y, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HAAA, KAAR and HAG thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PSKBP/8630013).

References

Abdel-Aziz, H. A., Abdel-Wahab, B. F. & Badria, F. A. (2010). Arch. Pharm. 343, 152–159. Google Scholar
Abdel-Aziz, H. A. & Mekawey, A. A. I. (2009). Eur. J. Med. Chem. 44, 3985–4997. Google Scholar
Abdel-Aziz, H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2640. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiang, J., Ipek, M., Suri, V., Tam, M., Xing, Y., Huang, N., Zhang, Y., Tobin, J., Mansour, T. S. & McKew, J. (2007). Bioorg. Med. Chem. 15, 4327–4664. Web of Science CrossRef Google Scholar