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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-Ethyl-N-(2-meth­­oxy­phen­yl)benzene­sulfonamide

aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 15 June 2010; accepted 16 June 2010; online 23 June 2010)

In the title mol­ecule, C15H17NO3S, the C—S—N—Cbenzene torsion angle is 81.45 (16)°, and the two aromatic rings form a dihedral angle of 45.83 (12)°. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains parallel to the b axis.

Related literature

For the biological activity of sulfonamides, see: Ozbek et al. (2007[Ozbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem. 15, 5105-5109.]); Parari et al. (2008[Parari, M. K., Panda, G., Srivastava, K. & Puri, S. K. (2008). Bioorg. Med. Chem. Lett. 18, 776-781.]). For related structures, see: Mariam et al. (2009[Mariam, I., Akkurt, M., Sharif, S., Akhtar, N. & Khan, I. U. (2009). Acta Cryst. E65, o2797.]); Arshad et al. (2009[Arshad, M. N., Khan, I. U., Akkurt, M. & Shafiq, M. (2009). Acta Cryst. E65, o1953-o1954.]); Asiri et al. (2009[Asiri, A. M., Akkurt, M., Khan, S. A., Arshad, M. N., Khan, I. U. & Sharif, H. M. A. (2009). Acta Cryst. E65, o1246-o1247.]); Khan et al. (2010[Khan, I. U., Sharif, S., Akkurt, M., Sajjad, A. & Ahmad, J. (2010). Acta Cryst. E66, o786.]); Akkurt et al. (2010a[Akkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1596.],b[Akkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o1559-o1560.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17NO3S

  • Mr = 291.37

  • Monoclinic, P 21 /c

  • a = 9.3098 (5) Å

  • b = 9.5664 (6) Å

  • c = 17.1949 (10) Å

  • β = 104.040 (2)°

  • V = 1485.65 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 296 K

  • 0.15 × 0.10 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 13197 measured reflections

  • 3670 independent reflections

  • 1963 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.157

  • S = 0.99

  • 3670 reflections

  • 183 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O2i 0.93 2.53 3.300 (3) 140
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Sulfonamides are known as biologically active compounds (Ozbek et al., 2007; Parari et al., 2008). As a contribution to a structural study of sulfonamide derivatives (Mariam et al., 2009; Arshad et al., 2009; Asiri et al., 2009; Khan et al., 2010; Akkurt et al., 2010a,b) we present here the title compound, (I).

The title molecule (Fig. 1) is bent at the S atoms with the C1—S1—N1—C9 torsion angle of 81.45 (16)°. The dihedral angle between the phenyl (C1–C6) and benzene (C9–C14) rings is 45.83 (12)°.

In the crystal structure of (I), weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into chains parallel to b axis.

Related literature top

For the biological activity of sulfonamides, see: Ozbek et al. (2007); Parari et al. (2008). For related structures, see: Mariam et al. (2009); Arshad et al. (2009\bbr00); Asiri et al. (2009); Khan et al. (2010); Akkurt et al. (2010a,b).

Experimental top

A mixture of N-(2-methoxyphenyl)benzenesulfonamide (1.24 g, 5.0 mmol), sodium hydride (0.24 g, 10 mmol) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min and then ethyl iodide (0.4 ml, 5.0 mmol) was added. The stirring was continued further for a period of 3 h and the contents were poured over crushed ice. The precipitated product was isolated, washed and re-crystallized from methanolic solution. It was crystallized by slow evaporation of the solvent. Yield 72%.

Refinement top

All H atoms bonded to C atoms were positioned geometrically and refined using a riding model, with C—H = 0.93Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) with Uiso(H) = 1.2Ueq(aromatic, methylene) and Uiso(H) = 1.5Ueq(methyl).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I) showing the atom labelling scheme, Displacement ellipsoids are drawn at the 30% probability level.
N-Ethyl-N-(2-methoxyphenyl)benzenesulfonamide top
Crystal data top
C15H17NO3SF(000) = 616
Mr = 291.37Dx = 1.303 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3431 reflections
a = 9.3098 (5) Åθ = 2.3–24.5°
b = 9.5664 (6) ŵ = 0.22 mm1
c = 17.1949 (10) ÅT = 296 K
β = 104.040 (2)°Block, colourless
V = 1485.65 (15) Å30.15 × 0.10 × 0.06 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
1963 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.045
Graphite monochromatorθmax = 28.3°, θmin = 3.1°
ϕ and ω scansh = 1210
13197 measured reflectionsk = 1112
3670 independent reflectionsl = 2022
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0842P)2]
where P = (Fo2 + 2Fc2)/3
3670 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C15H17NO3SV = 1485.65 (15) Å3
Mr = 291.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.3098 (5) ŵ = 0.22 mm1
b = 9.5664 (6) ÅT = 296 K
c = 17.1949 (10) Å0.15 × 0.10 × 0.06 mm
β = 104.040 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
1963 reflections with I > 2σ(I)
13197 measured reflectionsRint = 0.045
3670 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.157H-atom parameters constrained
S = 0.99Δρmax = 0.30 e Å3
3670 reflectionsΔρmin = 0.27 e Å3
183 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
S10.86267 (6)0.81474 (6)0.18075 (4)0.0619 (2)
O10.99631 (18)0.7591 (2)0.16733 (12)0.0964 (8)
O20.81194 (19)0.94809 (17)0.14864 (9)0.0771 (7)
O30.57342 (18)0.66902 (16)0.25621 (9)0.0675 (6)
N10.73281 (18)0.70249 (17)0.14324 (10)0.0532 (6)
C10.8828 (2)0.8200 (2)0.28471 (13)0.0557 (7)
C20.8216 (3)0.9285 (2)0.31844 (14)0.0687 (9)
C30.8335 (3)0.9308 (3)0.39875 (16)0.0899 (11)
C40.9055 (4)0.8251 (4)0.44612 (18)0.1036 (15)
C50.9646 (4)0.7163 (4)0.4127 (2)0.1047 (14)
C60.9558 (3)0.7136 (3)0.33214 (17)0.0809 (10)
C70.7640 (3)0.5514 (2)0.15704 (15)0.0723 (9)
C80.6825 (4)0.4652 (3)0.09012 (17)0.1080 (13)
C90.5821 (2)0.7500 (2)0.12968 (11)0.0476 (7)
C100.5011 (2)0.7321 (2)0.18716 (12)0.0498 (7)
C110.3558 (2)0.7784 (2)0.17143 (14)0.0633 (9)
C120.2933 (3)0.8395 (2)0.09883 (17)0.0740 (10)
C130.3707 (3)0.8566 (2)0.04225 (15)0.0722 (9)
C140.5157 (3)0.8111 (2)0.05732 (13)0.0605 (8)
C150.5112 (3)0.6721 (3)0.32343 (15)0.0878 (11)
H20.772101.000100.286200.0820*
H30.792601.004300.421500.1080*
H40.914400.827300.501200.1240*
H51.011100.643500.445000.1260*
H60.998600.640900.309700.0970*
H7A0.869300.535300.164500.0870*
H7B0.737100.523100.205800.0870*
H8A0.579500.463100.090500.1620*
H8B0.721400.371800.095700.1620*
H8C0.693200.504300.040400.1620*
H110.301200.768200.209700.0760*
H120.195500.869800.088300.0890*
H130.326600.898600.006400.0870*
H140.568800.821700.018400.0730*
H15A0.474900.764300.329500.1320*
H15B0.585500.647500.370700.1320*
H15C0.430900.606500.315700.1320*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0444 (4)0.0686 (4)0.0765 (4)0.0128 (3)0.0219 (3)0.0093 (3)
O10.0473 (10)0.1239 (15)0.1290 (16)0.0121 (10)0.0426 (10)0.0311 (12)
O20.0798 (12)0.0655 (11)0.0836 (11)0.0281 (9)0.0152 (8)0.0088 (8)
O30.0664 (10)0.0780 (11)0.0630 (10)0.0078 (8)0.0252 (8)0.0158 (7)
N10.0449 (10)0.0534 (11)0.0631 (11)0.0040 (8)0.0167 (8)0.0081 (8)
C10.0362 (11)0.0496 (12)0.0761 (15)0.0024 (9)0.0033 (10)0.0073 (10)
C20.0755 (17)0.0528 (14)0.0751 (16)0.0057 (12)0.0132 (12)0.0031 (11)
C30.111 (2)0.0808 (19)0.0776 (19)0.0022 (17)0.0224 (16)0.0168 (15)
C40.127 (3)0.106 (3)0.0640 (17)0.010 (2)0.0037 (17)0.0083 (16)
C50.110 (3)0.089 (2)0.087 (2)0.0113 (18)0.0303 (18)0.0097 (17)
C60.0691 (17)0.0680 (16)0.089 (2)0.0152 (13)0.0131 (14)0.0081 (13)
C70.0600 (15)0.0580 (15)0.1008 (18)0.0077 (11)0.0233 (13)0.0162 (12)
C80.143 (3)0.0672 (18)0.122 (2)0.0313 (18)0.048 (2)0.0282 (16)
C90.0446 (12)0.0434 (11)0.0553 (12)0.0076 (9)0.0130 (9)0.0070 (9)
C100.0464 (12)0.0459 (11)0.0576 (12)0.0058 (9)0.0135 (9)0.0012 (9)
C110.0455 (13)0.0638 (14)0.0839 (17)0.0052 (10)0.0224 (11)0.0003 (12)
C120.0492 (14)0.0662 (16)0.099 (2)0.0021 (11)0.0035 (13)0.0004 (13)
C130.0691 (18)0.0655 (15)0.0701 (16)0.0038 (12)0.0059 (13)0.0066 (12)
C140.0645 (15)0.0628 (14)0.0537 (13)0.0128 (11)0.0132 (11)0.0029 (10)
C150.093 (2)0.110 (2)0.0686 (17)0.0052 (17)0.0353 (14)0.0107 (14)
Geometric parameters (Å, º) top
S1—O11.4226 (19)C12—C131.354 (4)
S1—O21.4243 (17)C13—C141.382 (4)
S1—N11.6286 (18)C2—H20.9300
S1—C11.752 (2)C3—H30.9300
O3—C101.356 (2)C4—H40.9300
O3—C151.413 (3)C5—H50.9300
N1—C71.482 (3)C6—H60.9300
N1—C91.439 (3)C7—H7A0.9700
C1—C21.378 (3)C7—H7B0.9700
C1—C61.376 (3)C8—H8A0.9600
C2—C31.359 (4)C8—H8B0.9600
C3—C41.368 (5)C8—H8C0.9600
C4—C51.367 (5)C11—H110.9300
C5—C61.368 (4)C12—H120.9300
C7—C81.468 (4)C13—H130.9300
C9—C101.392 (3)C14—H140.9300
C9—C141.378 (3)C15—H15A0.9600
C10—C111.386 (3)C15—H15B0.9600
C11—C121.373 (4)C15—H15C0.9600
O1···C11i3.336 (3)C11···H15A2.6800
O1···C12i3.347 (3)C11···H15C2.9200
O2···C6ii3.300 (3)C15···H112.5800
O2···C143.113 (3)H2···O22.5300
O3···N12.734 (2)H2···C11v3.0800
O3···C23.383 (3)H2···H15Cv2.4600
O3···C72.965 (3)H3···H8Cviii2.4400
O3···C13.152 (3)H4···O1viii2.8900
O1···H11i2.7600H6···O12.6900
O1···H7A2.4400H6···O2vi2.5300
O1···H4iii2.8900H7A···O12.4400
O1···H12i2.7600H7A···C1vi3.0600
O1···H62.6900H7A···C2vi3.0000
O2···H13iv2.8800H7B···O32.3800
O2···H15Cv2.9100H7B···C102.9300
O2···H22.5300H8A···C92.8200
O2···H6ii2.5300H8A···H15Aix2.4700
O3···H7B2.3800H8C···C3iii3.0900
N1···O32.734 (2)H8C···H3iii2.4400
C1···O33.152 (3)H11···O1vii2.7600
C2···O33.383 (3)H11···C152.5800
C6···O2vi3.300 (3)H11···H15A2.2900
C6···C73.472 (4)H11···H15C2.4700
C7···C63.472 (4)H12···O1vii2.7600
C7···O32.965 (3)H13···O2iv2.8800
C11···O1vii3.336 (3)H14···H15Biii2.6000
C12···O1vii3.347 (3)H15A···C112.6800
C14···O23.113 (3)H15A···H112.2900
C1···H7Aii3.0600H15A···C8v2.9600
C2···H7Aii3.0000H15A···H8Av2.4700
C3···H8Cviii3.0900H15B···H14viii2.6000
C8···H15Aix2.9600H15C···C112.9200
C9···H8A2.8200H15C···H112.4700
C10···H7B2.9300H15C···O2ix2.9100
C11···H2ix3.0800H15C···H2ix2.4600
O1—S1—O2119.54 (11)C4—C3—H3120.00
O1—S1—N1106.47 (10)C3—C4—H4120.00
O1—S1—C1107.15 (11)C5—C4—H4120.00
O2—S1—N1107.01 (10)C4—C5—H5120.00
O2—S1—C1108.24 (10)C6—C5—H5120.00
N1—S1—C1107.96 (9)C1—C6—H6120.00
C10—O3—C15119.46 (18)C5—C6—H6120.00
S1—N1—C7118.81 (15)N1—C7—H7A109.00
S1—N1—C9117.18 (13)N1—C7—H7B109.00
C7—N1—C9118.65 (18)C8—C7—H7A109.00
S1—C1—C2119.88 (16)C8—C7—H7B109.00
S1—C1—C6119.90 (18)H7A—C7—H7B108.00
C2—C1—C6120.2 (2)C7—C8—H8A109.00
C1—C2—C3120.0 (2)C7—C8—H8B109.00
C2—C3—C4120.1 (3)C7—C8—H8C109.00
C3—C4—C5120.1 (3)H8A—C8—H8B109.00
C4—C5—C6120.6 (3)H8A—C8—H8C109.00
C1—C6—C5119.1 (3)H8B—C8—H8C109.00
N1—C7—C8112.2 (2)C10—C11—H11120.00
N1—C9—C10121.41 (17)C12—C11—H11120.00
N1—C9—C14119.11 (19)C11—C12—H12119.00
C10—C9—C14119.5 (2)C13—C12—H12119.00
O3—C10—C9115.92 (17)C12—C13—H13120.00
O3—C10—C11124.52 (19)C14—C13—H13120.00
C9—C10—C11119.56 (19)C9—C14—H14120.00
C10—C11—C12119.4 (2)C13—C14—H14120.00
C11—C12—C13121.5 (2)O3—C15—H15A109.00
C12—C13—C14119.6 (2)O3—C15—H15B109.00
C9—C14—C13120.5 (2)O3—C15—H15C109.00
C1—C2—H2120.00H15A—C15—H15B109.00
C3—C2—H2120.00H15A—C15—H15C109.00
C2—C3—H3120.00H15B—C15—H15C109.00
O1—S1—N1—C742.39 (19)S1—C1—C2—C3178.2 (2)
O1—S1—N1—C9163.78 (15)C6—C1—C2—C30.1 (4)
O2—S1—N1—C7171.30 (16)S1—C1—C6—C5177.1 (2)
O2—S1—N1—C934.87 (17)C2—C1—C6—C51.0 (4)
C1—S1—N1—C772.39 (18)C1—C2—C3—C40.4 (4)
C1—S1—N1—C981.45 (16)C2—C3—C4—C50.5 (5)
O1—S1—C1—C2144.01 (19)C3—C4—C5—C61.7 (6)
O1—S1—C1—C638.0 (2)C4—C5—C6—C11.9 (5)
O2—S1—C1—C213.9 (2)N1—C9—C10—O30.7 (3)
O2—S1—C1—C6168.12 (19)N1—C9—C10—C11179.48 (18)
N1—S1—C1—C2101.66 (19)C14—C9—C10—O3178.90 (18)
N1—S1—C1—C676.4 (2)C14—C9—C10—C111.2 (3)
C15—O3—C10—C9167.2 (2)N1—C9—C14—C13179.41 (18)
C15—O3—C10—C1112.7 (3)C10—C9—C14—C131.1 (3)
S1—N1—C7—C8148.4 (2)O3—C10—C11—C12179.24 (19)
C9—N1—C7—C858.1 (3)C9—C10—C11—C120.9 (3)
S1—N1—C9—C1093.0 (2)C10—C11—C12—C130.5 (3)
S1—N1—C9—C1488.8 (2)C11—C12—C13—C140.4 (3)
C7—N1—C9—C1060.9 (3)C12—C13—C14—C90.7 (3)
C7—N1—C9—C14117.4 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1/2, z+1/2; (iii) x, y+3/2, z1/2; (iv) x+1, y+2, z; (v) x+1, y+1/2, z+1/2; (vi) x+2, y1/2, z+1/2; (vii) x1, y, z; (viii) x, y+3/2, z+1/2; (ix) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O20.932.532.905 (3)104
C6—H6···O2vi0.932.533.300 (3)140
C7—H7A···O10.972.442.911 (3)109
C7—H7B···O30.972.382.965 (3)118
Symmetry code: (vi) x+2, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H17NO3S
Mr291.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)9.3098 (5), 9.5664 (6), 17.1949 (10)
β (°) 104.040 (2)
V3)1485.65 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.15 × 0.10 × 0.06
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13197, 3670, 1963
Rint0.045
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.157, 0.99
No. of reflections3670
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.533.300 (3)140
Symmetry code: (i) x+2, y1/2, z+1/2.
 

Footnotes

Additional corresponding author, e-mail: azizhej@hotmail.com.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

First citationAkkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1596.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAkkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o1559–o1560.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationArshad, M. N., Khan, I. U., Akkurt, M. & Shafiq, M. (2009). Acta Cryst. E65, o1953–o1954.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAsiri, A. M., Akkurt, M., Khan, S. A., Arshad, M. N., Khan, I. U. & Sharif, H. M. A. (2009). Acta Cryst. E65, o1246–o1247.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationKhan, I. U., Sharif, S., Akkurt, M., Sajjad, A. & Ahmad, J. (2010). Acta Cryst. E66, o786.  Web of Science CrossRef IUCr Journals Google Scholar
First citationMariam, I., Akkurt, M., Sharif, S., Akhtar, N. & Khan, I. U. (2009). Acta Cryst. E65, o2797.  Web of Science CrossRef IUCr Journals Google Scholar
First citationOzbek, N., Katircioglu, H., Karacan, N. & Baykal, T. (2007). Bioorg. Med. Chem. 15, 5105–5109.  Web of Science CrossRef PubMed Google Scholar
First citationParari, M. K., Panda, G., Srivastava, K. & Puri, S. K. (2008). Bioorg. Med. Chem. Lett. 18, 776–781.  PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds