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ISSN: 2056-9890

2-Nitro-N-phenyl­benzene­sulfonamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 20 July 2012; accepted 1 August 2012; online 4 August 2012)

In the title compound, C12H10N2O4S, the conformation of the N—H bond in the –SO2—NH– fragment is syn to the ortho-nitro group in the sulfonyl­benzene ring. The mol­ecule is twisted at the S—N bond, the C—N—S—C torsion angle being −72.83 (15)°. The dihedral angle between the benzene rings is 59.55 (7)°. The amide H atom and the nitro group O atom form an intra­molecular hydrogen bond, generating an S(7) motif. In the crystal, C—H⋯O hydrogen-bond inter­actions link the mol­ecules into S22(10) networks.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Alkan et al. (2011[Alkan, C., Tek, Y. & Kahraman, D. (2011). Turk. J. Chem. 35, 769-777.]); Bowes et al. (2003[Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1-o3.]); Gowda et al. (2000[Gowda, B. T., Paulus, H. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 791-800.]); Saeed et al. (2010[Saeed, A., Arshad, M. & Simpson, J. (2010). Acta Cryst. E66, o2808-o2809.]); Shahwar et al. (2012[Shahwar, D., Tahir, M. N., Chohan, M. M., Ahmad, N. & Raza, M. A. (2012). Acta Cryst. E68, o1160.]), of N-aroylsulfonamides, see: Suchetan et al. (2012[Suchetan, P. A., Foro, S., Gowda, B. T. & Nirmala, B. (2012). Acta Cryst. E68, o339.]), of N-chloro­aryl­sulfonamides, see: Gowda et al. (2005[Gowda, B. T., Damodara, N. & Jyothi, K. (2005). Int. J. Chem. Kinet. 37, 572-582.]); Shetty & Gowda (2004[Shetty, M. & Gowda, B. T. (2004). Z. Naturforsch. Teil B, 59, 63-72.]) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983[Gowda, B. T. & Mahadevappa, D. S. (1983). Talanta, 30, 359-362.]); Usha & Gowda (2006[Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N2O4S

  • Mr = 278.28

  • Monoclinic, P 21 /c

  • a = 13.308 (2) Å

  • b = 6.1629 (7) Å

  • c = 15.285 (2) Å

  • β = 100.80 (1)°

  • V = 1231.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 293 K

  • 0.48 × 0.42 × 0.42 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.880, Tmax = 0.893

  • 4580 measured reflections

  • 2516 independent reflections

  • 1942 reflections with I > 2σ(I)

  • Rint = 0.013

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.096

  • S = 1.04

  • 2516 reflections

  • 175 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O3 0.84 (1) 2.21 (2) 2.897 (2) 139 (2)
C3—H3⋯O4i 0.93 2.56 3.451 (2) 162
Symmetry code: (i) -x, -y-1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Alkan et al., 2011; Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010; Shahwar et al., 2012); N-aroylsulfonamides (Suchetan et al., 2012); N-chloroarylsulfonamides (Gowda et al., 2005; Shetty & Gowda, 2004) and N-bromoarylsulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N-(phenyl)-2-nitrobenzenesulfonamide has been determined (Fig. 1).

The conformation of the N—H bond in the —SO2—NH— segment is syn to the ortho-nitro group in the sulfonyl benzene ring, similar to that observed in N-(benzoyl)-2-nitrobenzenesulfonamide (I) (Suchetan et al., 2012). The molecule is twisted at the S—N bond with the torsional angle of -72.83 (15)°, compared to the value of -63.39 (22)° in (I).

The dihedral angle between the sulfonyl and the anilino rings is 59.55 (7)°, compared to the value of 88.6 (1)° in (I).

The amide H-atom showed intramolecular H-bonding with the O-atom of the ortho-nitro group in the sulfonyl benzene ring (Table 1).

In the crystal, the intermolecular C–H···O hydrogen bond interactions link the molecules. Part of the crystal structure is shown in Fig. 2.

Related literature top

For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Alkan et al. (2011); Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010); Shahwar et al. (2012), of N-aroylsulfonamides, see: Suchetan et al. (2012), of N-chloroarylsulfonamides, see: Gowda et al. (2005); Shetty & Gowda (2004) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983); Usha & Gowda (2006).

Experimental top

The title compound was prepared by treating 2-nitrobenzenesulfonylchloride with aniline in the stoichiometric ratio and boiling the reaction mixture for 15 minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(phenyl)-2-nitrobenzenesulfonamide was filtered under suction and washed thoroughly with cold water and dilute HCl to remove the excess sulfonylchloride and aniline, respectively. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation of the solvent at room temperature.

Refinement top

H atoms bonded to C were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å. The amino H atom was freely refined with the N—H distances restrained to 0.86 (1) Å. All H atoms were refined with isotropic displacement parameters set at 1.2 Ueq of the parent atom. The (-2 0 4) reflection was probably affected by the beamstop and was omitted from the refinement.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
2-Nitro-N-phenylbenzenesulfonamide top
Crystal data top
C12H10N2O4SF(000) = 576
Mr = 278.28Dx = 1.501 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1497 reflections
a = 13.308 (2) Åθ = 3.1–27.8°
b = 6.1629 (7) ŵ = 0.28 mm1
c = 15.285 (2) ÅT = 293 K
β = 100.80 (1)°Prism, colourless
V = 1231.4 (3) Å30.48 × 0.42 × 0.42 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2516 independent reflections
Radiation source: fine-focus sealed tube1942 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1616
Tmin = 0.880, Tmax = 0.893k = 47
4580 measured reflectionsl = 1819
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.051P)2 + 0.178P]
where P = (Fo2 + 2Fc2)/3
2516 reflections(Δ/σ)max = 0.001
175 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.34 e Å3
Crystal data top
C12H10N2O4SV = 1231.4 (3) Å3
Mr = 278.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.308 (2) ŵ = 0.28 mm1
b = 6.1629 (7) ÅT = 293 K
c = 15.285 (2) Å0.48 × 0.42 × 0.42 mm
β = 100.80 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2516 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1942 reflections with I > 2σ(I)
Tmin = 0.880, Tmax = 0.893Rint = 0.013
4580 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0351 restraint
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å3
2516 reflectionsΔρmin = 0.34 e Å3
175 parameters
Special details top

Experimental. Absorption correction: CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C10.18707 (12)0.0643 (3)0.09270 (10)0.0368 (4)
C20.13182 (12)0.1185 (3)0.05925 (10)0.0390 (4)
C30.08257 (14)0.2461 (3)0.11177 (12)0.0512 (4)
H30.04450.36550.08760.061*
C40.09012 (15)0.1954 (4)0.20065 (12)0.0590 (5)
H40.05820.28270.23690.071*
C50.14426 (14)0.0176 (4)0.23550 (11)0.0552 (5)
H50.14960.01520.29560.066*
C60.19116 (13)0.1139 (3)0.18203 (10)0.0464 (4)
H60.22600.23730.20610.056*
C70.43841 (12)0.1244 (3)0.07735 (10)0.0385 (4)
C80.46081 (14)0.0675 (3)0.12345 (11)0.0488 (4)
H80.41610.18470.11300.059*
C90.55091 (16)0.0829 (3)0.18565 (12)0.0587 (5)
H90.56660.21130.21720.070*
C100.61684 (15)0.0889 (4)0.20105 (12)0.0588 (5)
H100.67740.07640.24240.071*
C110.59370 (15)0.2795 (3)0.15553 (13)0.0561 (5)
H110.63870.39610.16590.067*
C120.50405 (14)0.2984 (3)0.09449 (11)0.0476 (4)
H120.48770.42900.06470.057*
N10.34907 (11)0.1444 (3)0.00839 (9)0.0478 (4)
H1N0.3328 (15)0.037 (2)0.0247 (11)0.057*
N20.12429 (12)0.1899 (2)0.03419 (9)0.0461 (4)
O10.17706 (11)0.2775 (2)0.05490 (9)0.0635 (4)
O20.27405 (10)0.4356 (2)0.08413 (8)0.0586 (4)
O30.19974 (11)0.1782 (3)0.06778 (8)0.0640 (4)
O40.04257 (10)0.2632 (2)0.07212 (9)0.0648 (4)
S10.24456 (3)0.25201 (7)0.02828 (3)0.04409 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0317 (7)0.0421 (9)0.0360 (8)0.0075 (7)0.0047 (6)0.0002 (7)
C20.0361 (8)0.0433 (9)0.0374 (8)0.0070 (7)0.0063 (6)0.0010 (7)
C30.0449 (10)0.0502 (11)0.0588 (11)0.0034 (9)0.0108 (8)0.0016 (8)
C40.0532 (11)0.0749 (14)0.0526 (11)0.0003 (11)0.0194 (9)0.0137 (10)
C50.0497 (10)0.0798 (14)0.0374 (9)0.0055 (11)0.0113 (8)0.0014 (9)
C60.0394 (9)0.0585 (11)0.0398 (9)0.0041 (8)0.0037 (7)0.0061 (8)
C70.0388 (8)0.0465 (10)0.0338 (8)0.0017 (7)0.0157 (6)0.0007 (7)
C80.0534 (10)0.0418 (10)0.0561 (10)0.0010 (8)0.0228 (9)0.0019 (8)
C90.0625 (12)0.0580 (13)0.0591 (12)0.0222 (11)0.0203 (10)0.0154 (9)
C100.0476 (10)0.0743 (15)0.0526 (11)0.0154 (11)0.0047 (9)0.0038 (10)
C110.0449 (10)0.0609 (13)0.0625 (12)0.0069 (9)0.0098 (9)0.0093 (9)
C120.0529 (10)0.0446 (10)0.0478 (10)0.0006 (8)0.0160 (8)0.0060 (8)
N10.0439 (8)0.0620 (10)0.0384 (7)0.0007 (7)0.0104 (6)0.0063 (7)
N20.0475 (9)0.0450 (8)0.0435 (8)0.0038 (7)0.0026 (7)0.0051 (6)
O10.0589 (8)0.0723 (10)0.0542 (8)0.0027 (7)0.0028 (6)0.0237 (7)
O20.0607 (8)0.0415 (7)0.0743 (9)0.0007 (6)0.0141 (7)0.0046 (6)
O30.0619 (9)0.0840 (10)0.0503 (7)0.0101 (8)0.0210 (7)0.0195 (7)
O40.0516 (8)0.0744 (10)0.0616 (8)0.0036 (7)0.0072 (7)0.0177 (7)
S10.0440 (3)0.0435 (3)0.0438 (2)0.00341 (19)0.00569 (18)0.00595 (18)
Geometric parameters (Å, º) top
C1—C21.390 (2)C8—C91.387 (3)
C1—C61.390 (2)C8—H80.9300
C1—S11.7819 (16)C9—C101.367 (3)
C2—C31.375 (2)C9—H90.9300
C2—N21.480 (2)C10—C111.370 (3)
C3—C41.379 (3)C10—H100.9300
C3—H30.9300C11—C121.375 (3)
C4—C51.364 (3)C11—H110.9300
C4—H40.9300C12—H120.9300
C5—C61.380 (3)N1—S11.6202 (16)
C5—H50.9300N1—H1N0.838 (9)
C6—H60.9300N2—O31.2125 (18)
C7—C121.377 (2)N2—O41.2193 (19)
C7—C81.380 (2)O1—S11.4213 (13)
C7—N11.439 (2)O2—S11.4276 (13)
C2—C1—C6117.40 (15)C10—C9—C8120.63 (18)
C2—C1—S1125.13 (12)C10—C9—H9119.7
C6—C1—S1117.28 (13)C8—C9—H9119.7
C3—C2—C1121.75 (15)C9—C10—C11120.03 (18)
C3—C2—N2116.12 (15)C9—C10—H10120.0
C1—C2—N2122.12 (14)C11—C10—H10120.0
C2—C3—C4119.42 (18)C10—C11—C12120.08 (18)
C2—C3—H3120.3C10—C11—H11120.0
C4—C3—H3120.3C12—C11—H11120.0
C5—C4—C3120.15 (18)C11—C12—C7120.13 (17)
C5—C4—H4119.9C11—C12—H12119.9
C3—C4—H4119.9C7—C12—H12119.9
C4—C5—C6120.32 (16)C7—N1—S1121.21 (11)
C4—C5—H5119.8C7—N1—H1N117.3 (14)
C6—C5—H5119.8S1—N1—H1N107.7 (14)
C5—C6—C1120.91 (17)O3—N2—O4123.79 (15)
C5—C6—H6119.5O3—N2—C2118.65 (14)
C1—C6—H6119.5O4—N2—C2117.52 (15)
C12—C7—C8120.10 (16)O1—S1—O2120.27 (8)
C12—C7—N1118.71 (15)O1—S1—N1107.35 (8)
C8—C7—N1121.14 (16)O2—S1—N1106.69 (8)
C7—C8—C9119.01 (18)O1—S1—C1107.54 (8)
C7—C8—H8120.5O2—S1—C1106.41 (8)
C9—C8—H8120.5N1—S1—C1108.10 (8)
C6—C1—C2—C30.2 (2)C8—C7—C12—C112.1 (3)
S1—C1—C2—C3174.56 (13)N1—C7—C12—C11175.41 (16)
C6—C1—C2—N2178.48 (14)C12—C7—N1—S184.88 (18)
S1—C1—C2—N26.8 (2)C8—C7—N1—S197.67 (17)
C1—C2—C3—C41.7 (3)C3—C2—N2—O3138.87 (18)
N2—C2—C3—C4177.03 (16)C1—C2—N2—O339.9 (2)
C2—C3—C4—C51.4 (3)C3—C2—N2—O439.1 (2)
C3—C4—C5—C60.5 (3)C1—C2—N2—O4142.16 (17)
C4—C5—C6—C12.1 (3)C7—N1—S1—O1171.43 (14)
C2—C1—C6—C51.7 (2)C7—N1—S1—O241.27 (16)
S1—C1—C6—C5176.89 (13)C7—N1—S1—C172.83 (15)
C12—C7—C8—C91.2 (2)C2—C1—S1—O137.94 (16)
N1—C7—C8—C9176.21 (15)C6—C1—S1—O1136.83 (14)
C7—C8—C9—C100.2 (3)C2—C1—S1—O2168.05 (14)
C8—C9—C10—C110.7 (3)C6—C1—S1—O26.72 (15)
C9—C10—C11—C120.2 (3)C2—C1—S1—N177.68 (15)
C10—C11—C12—C71.5 (3)C6—C1—S1—N1107.56 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.84 (1)2.21 (2)2.897 (2)139 (2)
C3—H3···O4i0.932.563.451 (2)162
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formulaC12H10N2O4S
Mr278.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.308 (2), 6.1629 (7), 15.285 (2)
β (°) 100.80 (1)
V3)1231.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.48 × 0.42 × 0.42
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.880, 0.893
No. of measured, independent and
observed [I > 2σ(I)] reflections
4580, 2516, 1942
Rint0.013
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.096, 1.04
No. of reflections2516
No. of parameters175
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.838 (9)2.210 (15)2.897 (2)139.2 (18)
C3—H3···O4i0.932.563.451 (2)162
Symmetry code: (i) x, y1, z.
 

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

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