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ISSN: 2056-9890

1-(3-Meth­­oxy­phen­yl)-2-(phenyl­sulfon­yl)ethan-1-one

aH. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 17 July 2012; accepted 19 July 2012; online 28 July 2012)

In the title compound, C15H14O4S, the dihedral angle between the benzene and phenyl rings is 88.74 (10)°. In the crystal, mol­ecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds and ππ stacking inter­actions [centroid–centroid distances = 3.6092 (13)–3.8651 (13) Å].

Related literature

For the biological activity of sulfone compounds, see: Dawood et al. (2010[Dawood, K. M., Kheder, N. A., Ragab, E. A. & Mohamed, S. N. (2010). Phosphorus Sulfur Silicon Relat. Elem. 185, 330-339.]); Suryakiran et al. (2007[Suryakiran, N., Prabhakar, P., Rajesh, K., Suresh, V. & Venkateswarlu, Y. (2007). J. Mol. Catal. A Chem. 270, 201-204.]); Siddiq et al. (2005[Siddiq, M., Mahmood, K. & Baloch, M. K. (2005). J. Chem. Soc. Pak. 27, 148-153.]); Lai et al. (2005[Lai, C., Xi, C., Jiang, Y. & Hua, R. (2005). Tetrahedron Lett. 46, 513-515.]). For related structures, see: Yousuf et al. (2012[Yousuf, S., Siddiqui, H., Farooq, R. & Choudhary, M. I. (2012). Acta Cryst. E68, o2090.]); Billing et al. (2006[Billing, D. G., Koning, C. B. de, Michael, J. P. & Yillah, I. (2006). Acta Cryst. E62, o5630-o5631.]); Pei et al. (2005[Pei, W., Wang, Y.-J., Sun, L. & Xiong, X.-B. (2005). Acta Cryst. E61, o3883-o3884.]); Gu et al. (2004[Gu, J.-M., Zhang, Y.-C. & Hu, X.-R. (2004). Acta Cryst. E60, o1115-o1116.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14O4S

  • Mr = 290.32

  • Triclinic, [P \overline 1]

  • a = 7.1290 (6) Å

  • b = 9.6101 (8) Å

  • c = 10.6999 (9) Å

  • α = 101.787 (2)°

  • β = 102.550 (2)°

  • γ = 95.879 (2)°

  • V = 692.13 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 298 K

  • 0.30 × 0.12 × 0.07 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.983

  • 7866 measured reflections

  • 2577 independent reflections

  • 2135 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.108

  • S = 1.06

  • 2577 reflections

  • 181 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯O2i 0.97 2.54 3.411 (3) 149
C7—H7B⋯O1ii 0.97 2.37 3.334 (3) 171
C11—H11A⋯O2iii 0.93 2.48 3.317 (3) 150
C15—H15A⋯O3iv 0.96 2.47 3.413 (3) 167
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+2, -z+1; (iii) x, y, z-1; (iv) x, y+1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Sulfone derivatives represent an important class of organic compounds and are known to have a wide range of biological activities including antiviral, antitubercular, anti-human rennin and antimicrobial activities (Dawood et al., 2010; Suryakiran et al., 2007; Siddiq et al., 2005; Lai et al., 2005). The title compound was obtained as part of our ongoing research to synthesize novel sulfone derivatives in order to study their different biological activities and structure-activity relationships.

In the title compound, C15H14O4S, the phenyl (C1–C6) and benzene (C9–C14) rings form a dihedral angle of 88.74 (10)°. The bond dimensions and angles are similar to those found in structurally related compounds (Yousuf et al., 2012; Billing et al., 2006; Pei et al., 2005; Gu et al., 2004). In the crystal structure (Fig. 2), the molecules are linked to form a three-dimensional network by C7–H7A···O2, C7–H7B···O1, C11–H11A···O2 and C15–H15A···O3 hydrogen interactions (Table 1) and by π···π stacking interactions [Cg1···Cg1i, 3.8651 (13) Å; Cg2···Cg2ii, 3.6092 (12) Å; Cg2···Cg2iii, 3.7240 (13) Å. Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively. Symmetry codes: (i) -x, 1-y, 1-z; (ii) -x, 2-y, -z; (iii) 1-x, 2-y, -z].

Related literature top

For the biological activity of sulfone compounds, see: Dawood et al. (2010); Suryakiran et al. (2007); Siddiq et al. (2005); Lai et al. (2005). For related structures, see: Yousuf et al. (2012); Billing et al. (2006); Pei et al. (2005); Gu et al. (2004).

Experimental top

In a 50 ml round-bottomed flask, benzene sulfonyl chloriode (6 mmol), water (15 ml), sodium bicarbonate (0.840 g, 10 mmol) and sodium sulfite (1.26 g, 10 mmol) were added and refluxed for about 4–7 h. The progress of the reaction was monitored by TLC until complete disappearance of the starting material indicated the formation of sodium sulfinate salt. 2-Bromo-3'-methoxyacetophenone (2 mmol) in ethanol (7 ml) was then added and the mixture refluxed for 7 h till completion of reaction (TLC analysis). After cooling, the reaction mixture was neutralized by adding dilute HCl. The precipitate obtained was filtered and recrystallized from ethanol to obtain crystals of 1-(2-methoxyphenyl)-3-(phenylsulfonyl)-1-ethanone (0.49 g, 84% yield) suitable for single-crystal X-ray diffraction studies.

Refinement top

H atoms on methyl, methylene and methine carbon atoms were positioned geometrically with C—H = 0.96 Å, 0.97 Å, and 0.93 Å, respectively, and constrained to ride on their parent atoms with Uiso(H)= 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Structure description top

Sulfone derivatives represent an important class of organic compounds and are known to have a wide range of biological activities including antiviral, antitubercular, anti-human rennin and antimicrobial activities (Dawood et al., 2010; Suryakiran et al., 2007; Siddiq et al., 2005; Lai et al., 2005). The title compound was obtained as part of our ongoing research to synthesize novel sulfone derivatives in order to study their different biological activities and structure-activity relationships.

In the title compound, C15H14O4S, the phenyl (C1–C6) and benzene (C9–C14) rings form a dihedral angle of 88.74 (10)°. The bond dimensions and angles are similar to those found in structurally related compounds (Yousuf et al., 2012; Billing et al., 2006; Pei et al., 2005; Gu et al., 2004). In the crystal structure (Fig. 2), the molecules are linked to form a three-dimensional network by C7–H7A···O2, C7–H7B···O1, C11–H11A···O2 and C15–H15A···O3 hydrogen interactions (Table 1) and by π···π stacking interactions [Cg1···Cg1i, 3.8651 (13) Å; Cg2···Cg2ii, 3.6092 (12) Å; Cg2···Cg2iii, 3.7240 (13) Å. Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively. Symmetry codes: (i) -x, 1-y, 1-z; (ii) -x, 2-y, -z; (iii) 1-x, 2-y, -z].

For the biological activity of sulfone compounds, see: Dawood et al. (2010); Suryakiran et al. (2007); Siddiq et al. (2005); Lai et al. (2005). For related structures, see: Yousuf et al. (2012); Billing et al. (2006); Pei et al. (2005); Gu et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound. Only hydrogen atoms involved in hydrogen bonding (dashed lines) are shown.
1-(3-Methoxyphenyl)-2-(phenylsulfonyl)ethan-1-one top
Crystal data top
C15H14O4SZ = 2
Mr = 290.32F(000) = 304
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1290 (6) ÅCell parameters from 2142 reflections
b = 9.6101 (8) Åθ = 2.2–24.2°
c = 10.6999 (9) ŵ = 0.24 mm1
α = 101.787 (2)°T = 298 K
β = 102.550 (2)°Plate, colourless
γ = 95.879 (2)°0.30 × 0.12 × 0.07 mm
V = 692.13 (10) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2577 independent reflections
Radiation source: fine-focus sealed tube2135 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ω scanθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 88
Tmin = 0.931, Tmax = 0.983k = 1111
7866 measured reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.113P]
where P = (Fo2 + 2Fc2)/3
2577 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C15H14O4Sγ = 95.879 (2)°
Mr = 290.32V = 692.13 (10) Å3
Triclinic, P1Z = 2
a = 7.1290 (6) ÅMo Kα radiation
b = 9.6101 (8) ŵ = 0.24 mm1
c = 10.6999 (9) ÅT = 298 K
α = 101.787 (2)°0.30 × 0.12 × 0.07 mm
β = 102.550 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2577 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2135 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.983Rint = 0.026
7866 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.06Δρmax = 0.24 e Å3
2577 reflectionsΔρmin = 0.29 e Å3
181 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
xyzUiso*/Ueq
S10.22994 (8)0.83326 (5)0.47049 (5)0.04481 (19)
O10.4151 (2)0.78524 (16)0.49651 (15)0.0599 (4)
O20.1737 (2)0.91873 (16)0.57906 (14)0.0597 (4)
O30.2985 (3)0.75030 (17)0.20387 (17)0.0726 (5)
O40.2706 (3)1.33137 (17)0.10446 (16)0.0669 (5)
C10.1457 (3)0.7024 (2)0.3856 (2)0.0519 (5)
H1B0.17760.79310.41360.062*
C20.2891 (3)0.5848 (3)0.3324 (2)0.0608 (6)
H2B0.41890.59600.32430.073*
C30.2412 (4)0.4505 (3)0.2909 (2)0.0600 (6)
H3A0.33870.37140.25560.072*
C40.0507 (4)0.4333 (2)0.3017 (2)0.0579 (6)
H4A0.01940.34240.27360.069*
C50.0956 (3)0.5502 (2)0.3541 (2)0.0489 (5)
H5A0.22510.53880.36050.059*
C60.0467 (3)0.6838 (2)0.39682 (18)0.0411 (5)
C70.2252 (3)0.9421 (2)0.35511 (19)0.0432 (5)
H7A0.09770.97130.33630.052*
H7B0.31931.02860.39580.052*
C80.2679 (3)0.8732 (2)0.2256 (2)0.0462 (5)
C90.2659 (3)0.9613 (2)0.12651 (19)0.0411 (5)
C100.2567 (3)0.8914 (2)0.0027 (2)0.0469 (5)
H10A0.25370.79230.02500.056*
C110.2523 (3)0.9691 (3)0.0966 (2)0.0520 (6)
H11A0.24650.92220.18280.062*
C120.2562 (3)1.1161 (3)0.0658 (2)0.0506 (5)
H12A0.25271.16760.13080.061*
C130.2653 (3)1.1867 (2)0.0624 (2)0.0462 (5)
C140.2706 (3)1.1092 (2)0.1588 (2)0.0444 (5)
H14A0.27731.15640.24500.053*
C150.2437 (5)1.4133 (3)0.0078 (3)0.0859 (9)
H15A0.25091.51270.04980.129*
H15B0.11861.37940.05230.129*
H15C0.34341.40330.03950.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0551 (3)0.0411 (3)0.0331 (3)0.0025 (2)0.0064 (2)0.0042 (2)
O10.0535 (9)0.0548 (10)0.0617 (10)0.0037 (7)0.0026 (7)0.0119 (8)
O20.0897 (12)0.0524 (9)0.0327 (8)0.0070 (8)0.0155 (8)0.0016 (7)
O30.1229 (16)0.0439 (10)0.0609 (11)0.0186 (10)0.0449 (10)0.0079 (8)
O40.0959 (13)0.0517 (10)0.0565 (10)0.0158 (9)0.0211 (9)0.0156 (8)
C10.0570 (14)0.0500 (13)0.0490 (13)0.0111 (11)0.0152 (10)0.0088 (10)
C20.0487 (13)0.0663 (16)0.0661 (16)0.0063 (12)0.0135 (11)0.0141 (13)
C30.0601 (15)0.0551 (14)0.0585 (15)0.0078 (11)0.0097 (12)0.0125 (11)
C40.0695 (16)0.0400 (12)0.0620 (15)0.0043 (11)0.0178 (12)0.0071 (11)
C50.0520 (12)0.0441 (12)0.0503 (13)0.0053 (10)0.0160 (10)0.0077 (10)
C60.0506 (12)0.0410 (11)0.0317 (10)0.0041 (9)0.0116 (9)0.0084 (8)
C70.0530 (12)0.0370 (11)0.0372 (11)0.0017 (9)0.0128 (9)0.0041 (9)
C80.0522 (12)0.0428 (12)0.0421 (12)0.0022 (10)0.0175 (10)0.0029 (9)
C90.0354 (10)0.0471 (12)0.0380 (11)0.0028 (9)0.0109 (8)0.0035 (9)
C100.0464 (12)0.0487 (12)0.0402 (11)0.0018 (10)0.0117 (9)0.0000 (9)
C110.0475 (12)0.0672 (16)0.0345 (11)0.0034 (11)0.0083 (9)0.0011 (10)
C120.0452 (12)0.0674 (15)0.0403 (12)0.0072 (11)0.0094 (9)0.0167 (11)
C130.0437 (11)0.0486 (13)0.0464 (12)0.0070 (9)0.0121 (9)0.0102 (10)
C140.0462 (11)0.0493 (12)0.0371 (11)0.0070 (9)0.0143 (9)0.0045 (9)
C150.127 (3)0.0563 (17)0.0755 (19)0.0147 (17)0.0154 (17)0.0275 (14)
Geometric parameters (Å, º) top
S1—O11.4317 (16)C7—C81.517 (3)
S1—O21.4371 (15)C7—H7A0.9700
S1—C61.760 (2)C7—H7B0.9700
S1—C71.771 (2)C8—C91.485 (3)
O3—C81.208 (2)C9—C141.388 (3)
O4—C131.365 (3)C9—C101.393 (3)
O4—C151.415 (3)C10—C111.366 (3)
C1—C21.376 (3)C10—H10A0.9300
C1—C61.384 (3)C11—C121.379 (3)
C1—H1B0.9300C11—H11A0.9300
C2—C31.379 (3)C12—C131.385 (3)
C2—H2B0.9300C12—H12A0.9300
C3—C41.368 (3)C13—C141.386 (3)
C3—H3A0.9300C14—H14A0.9300
C4—C51.383 (3)C15—H15A0.9600
C4—H4A0.9300C15—H15B0.9600
C5—C61.379 (3)C15—H15C0.9600
C5—H5A0.9300
O1—S1—O2117.84 (10)S1—C7—H7B108.3
O1—S1—C6109.38 (10)H7A—C7—H7B107.4
O2—S1—C6108.11 (10)O3—C8—C9121.74 (19)
O1—S1—C7109.20 (10)O3—C8—C7120.8 (2)
O2—S1—C7104.93 (9)C9—C8—C7117.46 (18)
C6—S1—C7106.79 (9)C14—C9—C10119.73 (19)
C13—O4—C15117.60 (19)C14—C9—C8122.06 (18)
C2—C1—C6119.1 (2)C10—C9—C8118.21 (18)
C2—C1—H1B120.5C11—C10—C9119.7 (2)
C6—C1—H1B120.5C11—C10—H10A120.2
C1—C2—C3120.3 (2)C9—C10—H10A120.2
C1—C2—H2B119.9C10—C11—C12121.1 (2)
C3—C2—H2B119.9C10—C11—H11A119.5
C4—C3—C2120.2 (2)C12—C11—H11A119.5
C4—C3—H3A119.9C11—C12—C13119.7 (2)
C2—C3—H3A119.9C11—C12—H12A120.2
C3—C4—C5120.4 (2)C13—C12—H12A120.2
C3—C4—H4A119.8O4—C13—C12124.9 (2)
C5—C4—H4A119.8O4—C13—C14115.31 (19)
C6—C5—C4119.0 (2)C12—C13—C14119.8 (2)
C6—C5—H5A120.5C13—C14—C9119.98 (19)
C4—C5—H5A120.5C13—C14—H14A120.0
C5—C6—C1121.0 (2)C9—C14—H14A120.0
C5—C6—S1120.11 (16)O4—C15—H15A109.5
C1—C6—S1118.89 (16)O4—C15—H15B109.5
C8—C7—S1115.89 (15)H15A—C15—H15B109.5
C8—C7—H7A108.3O4—C15—H15C109.5
S1—C7—H7A108.3H15A—C15—H15C109.5
C8—C7—H7B108.3H15B—C15—H15C109.5
C6—C1—C2—C30.0 (3)S1—C7—C8—C9179.81 (14)
C1—C2—C3—C40.4 (4)O3—C8—C9—C14166.6 (2)
C2—C3—C4—C50.0 (4)C7—C8—C9—C1414.8 (3)
C3—C4—C5—C60.8 (3)O3—C8—C9—C1014.1 (3)
C4—C5—C6—C11.2 (3)C7—C8—C9—C10164.46 (18)
C4—C5—C6—S1177.26 (16)C14—C9—C10—C110.1 (3)
C2—C1—C6—C50.8 (3)C8—C9—C10—C11179.21 (18)
C2—C1—C6—S1177.68 (17)C9—C10—C11—C120.2 (3)
O1—S1—C6—C510.3 (2)C10—C11—C12—C130.2 (3)
O2—S1—C6—C5139.83 (17)C15—O4—C13—C127.2 (3)
C7—S1—C6—C5107.72 (18)C15—O4—C13—C14173.1 (2)
O1—S1—C6—C1168.16 (16)C11—C12—C13—O4179.8 (2)
O2—S1—C6—C138.66 (18)C11—C12—C13—C140.0 (3)
C7—S1—C6—C173.79 (18)O4—C13—C14—C9179.97 (18)
O1—S1—C7—C856.31 (17)C12—C13—C14—C90.3 (3)
O2—S1—C7—C8176.48 (15)C10—C9—C14—C130.3 (3)
C6—S1—C7—C861.87 (17)C8—C9—C14—C13178.97 (18)
S1—C7—C8—O31.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O2i0.972.543.411 (3)149
C7—H7B···O1ii0.972.373.334 (3)171
C11—H11A···O2iii0.932.483.317 (3)150
C15—H15A···O3iv0.962.473.413 (3)167
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x, y, z1; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H14O4S
Mr290.32
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.1290 (6), 9.6101 (8), 10.6999 (9)
α, β, γ (°)101.787 (2), 102.550 (2), 95.879 (2)
V3)692.13 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.30 × 0.12 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.931, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
7866, 2577, 2135
Rint0.026
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.108, 1.06
No. of reflections2577
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···O2i0.97002.54003.411 (3)149.00
C7—H7B···O1ii0.97002.37003.334 (3)171.00
C11—H11A···O2iii0.93002.48003.317 (3)150.00
C15—H15A···O3iv0.96002.47003.413 (3)167.00
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+2, z+1; (iii) x, y, z1; (iv) x, y+1, z.
 

Acknowledgements

The authors are thankful to the Higher Education Commission (HEC) Pakistan for providing financial support under the National Research Support Program for Universities.

References

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