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

Journal logoIUCrDATA
ISSN: 2414-3146

5-[(Benzo[d][1,3]dioxol-5-yl)meth­yl]-3-[4-(pyridin-2-yl)phen­yl]-4,5-di­hydro­isoxazole

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and cDepartment of Physics, St Philomena's College, Mysore, India
*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

Edited by S. Parkin, University of Kentucky, USA (Received 13 January 2017; accepted 19 February 2017; online 28 February 2017)

In the mol­ecule of the title compound C22H18N2O3, the benzodioxole and di­hydro­isoxazole rings are bridged via a methyl­ene (CH2) group. The linkage is disordered over two positions with a occupancy factors of 0.887 (5) and 0.113 (5). The di­hydro­isoxazole and pyridine rings exhibit syn-clinal and anti-periplanar conformations with respect to the benzodioxole and benzene ring groups, as qu­anti­fied by the torsion angle values of 70.7 (3) and 157.00 (17)°. Aside from van der Waals contacts, there are no significant inter­molecular inter­actions.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Isoxazolines are heterocyclic compounds bearing nitro­gen and oxygen at adjacent positions of five-membered rings. Substituted isoxazolines have demonstrated diverse properties, including their use as anti-bacterial (Shah & Desai, 2007[Shah, T. & Desai, V. (2007). J. Serb. Chem. Soc. 72, 443-449.]), anti-cancer (Kamal et al., 2010[Kamal, A., Reddy, J. S., Ramaiah, M. J., Dastagiri, D., Bharathi, E. V., Azhar, M. A., Sultana, F., Pushpavalli, S., Pal-Bhadra, M. & Juvekar, A. (2010). Eur. J. Med. Chem. 45, 3924-3937.]), anti-inflammatory (Habeeb et al., 2001[Habeeb, A. G., Praveen Rao, P. & Knaus, E. E. (2001). J. Med. Chem. 44, 2921-2927.]) and anti­fungal agents (Dighade et al., 2003[Dighade, S., Patil, S., Chincholkar, M. & Dighade, N. (2003). Asian J. Chem. 15, 450-454.]). In addition, isoxazolines produced from cyclo­addition reactions of nitrile oxide and alkenes have been used as masked β-amino alcohols and β-hy­droxy carbonyl aldolates. With this background and as a part of our continuing study of isoxazole derivatives (Chandra et al., 2013[Chandra, Raghu, K., Jeyaseelan, S., Umesha, K. B. & Mahendra, M. (2013). Acta Cryst. E69, o987.]), the title compound was synthesized and its crystal structure determined.

In the title compound (Fig. 1[link]), there is a small amount of disorder of the methyl­ene linkage between the benzodioxazole and isoxazoline rings, involving atoms C10 and C11, with refined occupancies of 0.887 (5) and 0.113 (5), respectively, for the major and minor components. The di­hydro­isoxazole and pyridine rings exhibit syn-clinal and anti-periplanar orientations with respect to the benzodioxole and phenyl rings, as indicated by the torsion angles of 70.7 (3)° (O12—C11—C10—C7) and 157.00 (17)° (C18—C19—C22—N27), respectively. In addition, the benzene ring makes dihedral angles of 17.54 (11) and 24.82 (9)° with the mean planes of the di­hydro­isoxazole and pyridine rings, respectively.

[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at 50° probability. Atoms C10 and C11 are shown for the major disorder component [occupancy = 0.887 (5)]. The minor component atoms have been omitted to enhance clarity.

Aside from van der Waals contacts, there are no significant inter­molecular inter­actions. The packing of the mol­ecules viewed down the a axis is shown in Fig. 2[link].

[Figure 2]
Figure 2
A packing diagram viewed parallel to the a axis. H atoms have been omitted for the sake of clarity.

Synthesis and crystallization

A solution of 4-(pyridin-2-yl)benzaldehyde (0.002 mol), hydroxyl­amine hydro­chloride (0.002 mol) and tri­ethyl­amine (0.0025 mol) in DMF was stirred at room temperature for 6 h. After completion of the reaction (monitored by TLC), crushed ice was added to the reaction mixture and the precipitated solid product (an oxime) was filtered, washed with hexane and dried. N-chloro­succinimide (0.0015 mol) and tri­ethyl­amine (0.0015 mol) were added to a solution of the oxime (0.001 mol) and safrole (0.0012 mol) in DMF at 0°C. This reaction mixture was stirred at room temperature for 12 h. After completion of reaction, water was added and the product was extracted with ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure. The crude product was purified using silica gel column chromatography. Recrystallization from absolute ethanol solution by slow evaporation yielded block-shaped single crystals after five days.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The disordered positions of the atoms C10 and C11, located between the benzodioxole and di­hydro­isoxazole rings, were refined with an occupancy ratio of 0.887 (5):0.113 (5).

Table 1
Experimental details

Crystal data
Chemical formula C22H18N2O3
Mr 358.38
Crystal system, space group Monoclinic, P21/c
Temperature (K) 293
a, b, c (Å) 17.548 (5), 8.719 (3), 12.237 (4)
β (°) 108.380 (9)
V3) 1776.8 (9)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.30 × 0.25 × 0.20
 
Data collection
Diffractometer Bruker MicroStar microfocus rotating anode
No. of measured, independent and observed [I > 2σ(I)] reflections 12236, 3242, 2353
Rint 0.067
(sin θ/λ)max−1) 0.602
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.127, 1.05
No. of reflections 3242
No. of parameters 263
No. of restraints 60
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.15, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2016/6 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016/6 (Sheldrick, 2015) and PLATON (Spek, 2009).

5-[(Benzo[d][1,3]dioxol-5-yl)methyl]-3-[4-(pyridin-2-yl)phenyl]-4,5-dihydroisoxazole top
Crystal data top
C22H18N2O3F(000) = 752
Mr = 358.38Dx = 1.340 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.548 (5) ÅCell parameters from 3242 reflections
b = 8.719 (3) Åθ = 2.5–25.4°
c = 12.237 (4) ŵ = 0.09 mm1
β = 108.380 (9)°T = 293 K
V = 1776.8 (9) Å3Block, colourless
Z = 40.30 × 0.25 × 0.20 mm
Data collection top
Bruker MicroStar microfocus rotating anode
diffractometer
Rint = 0.067
φ and ω scansθmax = 25.4°, θmin = 2.5°
12236 measured reflectionsh = 2119
3242 independent reflectionsk = 1010
2353 reflections with I > 2σ(I)l = 1414
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0725P)2]
where P = (Fo2 + 2Fc2)/3
3242 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.15 e Å3
60 restraintsΔρmin = 0.16 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.47963 (13)0.9248 (3)0.34808 (19)0.0910 (7)
H1A0.4764641.0301740.3215320.109*
H1B0.5323510.9083130.4035000.109*
O20.41886 (8)0.89620 (18)0.40031 (11)0.0904 (5)
C30.36100 (10)0.8108 (2)0.31934 (14)0.0573 (5)
C40.39006 (10)0.7669 (2)0.23254 (15)0.0590 (5)
O50.46718 (7)0.82244 (18)0.25346 (12)0.0840 (5)
C60.28619 (10)0.7700 (2)0.32070 (14)0.0599 (5)
H60.2671610.8013040.3799780.072*
C80.26959 (11)0.6370 (2)0.14350 (15)0.0639 (5)
H80.2377220.5778150.0830710.077*
C90.34576 (11)0.6787 (2)0.14300 (15)0.0705 (6)
H90.3656400.6479850.0844230.085*
C70.23922 (10)0.67991 (18)0.23030 (14)0.0516 (4)0.887 (5)
C100.15409 (14)0.6325 (3)0.2197 (2)0.0547 (6)0.887 (5)
H10A0.1175420.6921280.1584540.066*0.887 (5)
H10B0.1473340.5256430.1965200.066*0.887 (5)
C110.12945 (13)0.6508 (2)0.3270 (2)0.0424 (6)0.887 (5)
H110.1702760.6045780.3927710.051*0.887 (5)
O120.12162 (6)0.81353 (11)0.34924 (10)0.0531 (3)0.887 (5)
C150.04667 (9)0.58461 (17)0.31803 (14)0.0499 (4)0.887 (5)
H15A0.0131530.5735400.2385290.060*0.887 (5)
H15B0.0510540.4865000.3569060.060*0.887 (5)
C7'0.23922 (10)0.67991 (18)0.23030 (14)0.0516 (4)0.113 (5)
C10'0.1723 (11)0.582 (2)0.276 (2)0.054 (3)0.113 (5)
H10C0.1571340.4879970.2320270.065*0.113 (5)
H10D0.1960030.5547480.3566130.065*0.113 (5)
C11'0.1014 (11)0.6773 (18)0.2615 (18)0.047 (3)0.113 (5)
H11'0.0742370.7084140.1817130.057*0.113 (5)
O12'0.12162 (6)0.81353 (11)0.34924 (10)0.0531 (3)0.113 (5)
C15'0.04667 (9)0.58461 (17)0.31803 (14)0.0499 (4)0.113 (5)
H15C0.0030580.5340730.2600510.060*0.113 (5)
H15D0.0775130.5085250.3717650.060*0.113 (5)
N130.05736 (8)0.83097 (14)0.39460 (12)0.0506 (4)
C140.01581 (9)0.70717 (15)0.37897 (12)0.0398 (4)
C160.05616 (8)0.69760 (15)0.41597 (12)0.0393 (4)
C170.07063 (9)0.80733 (16)0.49036 (13)0.0455 (4)
H170.0337760.8860520.5177430.055*
C180.13835 (9)0.80089 (16)0.52372 (13)0.0473 (4)
H180.1460390.8741310.5744930.057*
C190.19610 (9)0.68566 (16)0.48246 (12)0.0426 (4)
C200.18195 (9)0.57667 (17)0.40750 (12)0.0465 (4)
H200.2195420.4995870.3785800.056*
C210.11317 (9)0.58109 (16)0.37545 (12)0.0447 (4)
H210.1046220.5060830.3265430.054*
C220.26850 (10)0.67674 (18)0.52005 (14)0.0498 (4)
C230.27040 (12)0.7388 (2)0.62257 (17)0.0738 (6)
H230.2258850.7914380.6691420.089*
C240.33721 (13)0.7237 (3)0.6566 (2)0.0890 (7)
H240.3384530.7650190.7261040.107*
C250.40116 (14)0.6478 (3)0.5874 (2)0.0954 (8)
H250.4473970.6351610.6081230.114*
C260.39649 (14)0.5894 (3)0.4855 (2)0.1125 (10)
H260.4409030.5371750.4383270.135*
N270.33213 (10)0.6029 (2)0.44961 (15)0.0849 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0725 (13)0.1224 (19)0.0919 (15)0.0282 (13)0.0456 (12)0.0187 (14)
O20.0684 (8)0.1366 (13)0.0756 (9)0.0439 (9)0.0362 (7)0.0360 (9)
C30.0549 (10)0.0713 (12)0.0488 (10)0.0075 (9)0.0207 (8)0.0040 (8)
C40.0497 (10)0.0810 (12)0.0518 (10)0.0025 (9)0.0240 (8)0.0077 (9)
O50.0583 (8)0.1301 (13)0.0742 (9)0.0154 (8)0.0360 (7)0.0085 (9)
C60.0603 (11)0.0757 (12)0.0526 (10)0.0100 (9)0.0306 (8)0.0120 (9)
C80.0614 (11)0.0793 (13)0.0529 (10)0.0003 (9)0.0208 (8)0.0142 (9)
C90.0661 (12)0.1025 (16)0.0512 (11)0.0064 (11)0.0302 (9)0.0079 (10)
C70.0536 (10)0.0527 (10)0.0513 (9)0.0013 (8)0.0205 (8)0.0056 (8)
C100.0606 (14)0.0617 (15)0.0455 (14)0.0097 (11)0.0218 (11)0.0101 (11)
C110.0484 (12)0.0368 (9)0.0434 (14)0.0023 (8)0.0162 (10)0.0014 (8)
O120.0586 (7)0.0405 (6)0.0691 (8)0.0076 (5)0.0328 (6)0.0050 (5)
C150.0565 (10)0.0413 (9)0.0570 (10)0.0056 (7)0.0253 (8)0.0051 (7)
C7'0.0536 (10)0.0527 (10)0.0513 (9)0.0013 (8)0.0205 (8)0.0056 (8)
C10'0.059 (6)0.050 (7)0.053 (8)0.010 (5)0.016 (6)0.000 (6)
C11'0.056 (6)0.043 (6)0.039 (7)0.016 (5)0.011 (6)0.001 (5)
O12'0.0586 (7)0.0405 (6)0.0691 (8)0.0076 (5)0.0328 (6)0.0050 (5)
C15'0.0565 (10)0.0413 (9)0.0570 (10)0.0056 (7)0.0253 (8)0.0051 (7)
N130.0569 (8)0.0387 (7)0.0624 (9)0.0057 (6)0.0277 (7)0.0041 (6)
C140.0465 (8)0.0329 (8)0.0381 (8)0.0003 (7)0.0104 (6)0.0028 (6)
C160.0448 (9)0.0329 (8)0.0390 (8)0.0012 (6)0.0115 (6)0.0028 (6)
C170.0516 (9)0.0338 (8)0.0511 (9)0.0049 (7)0.0162 (7)0.0038 (7)
C180.0572 (10)0.0365 (8)0.0505 (9)0.0013 (7)0.0203 (8)0.0060 (7)
C190.0454 (9)0.0402 (8)0.0412 (8)0.0008 (7)0.0121 (7)0.0031 (6)
C200.0506 (9)0.0427 (9)0.0454 (8)0.0109 (7)0.0142 (7)0.0064 (7)
C210.0546 (9)0.0372 (8)0.0435 (8)0.0044 (7)0.0173 (7)0.0079 (7)
C220.0502 (9)0.0494 (9)0.0510 (9)0.0015 (8)0.0177 (8)0.0018 (7)
C230.0637 (12)0.0994 (15)0.0632 (12)0.0121 (10)0.0270 (9)0.0261 (11)
C240.0831 (15)0.1189 (19)0.0782 (14)0.0061 (14)0.0442 (12)0.0245 (13)
C250.0810 (15)0.1163 (19)0.1119 (19)0.0210 (14)0.0634 (15)0.0224 (15)
C260.0797 (15)0.151 (2)0.128 (2)0.0545 (15)0.0627 (15)0.0619 (18)
N270.0682 (11)0.1091 (14)0.0893 (12)0.0340 (10)0.0419 (9)0.0387 (11)
Geometric parameters (Å, º) top
C1—O51.423 (2)C11'—O12'1.565 (15)
C1—O21.427 (2)C11'—C15'1.573 (15)
O2—C31.390 (2)O12'—N131.4134 (15)
C3—C61.365 (2)C15'—C141.499 (2)
C3—C41.370 (2)N13—C141.2827 (18)
C4—C91.364 (3)C14—C161.4723 (19)
C4—O51.383 (2)C16—C171.398 (2)
C6—C7'1.395 (2)C16—C211.402 (2)
C6—C71.395 (2)C17—C181.374 (2)
C8—C7'1.382 (2)C18—C191.403 (2)
C8—C71.382 (2)C19—C201.396 (2)
C8—C91.387 (2)C19—C221.483 (2)
C7—C101.516 (2)C20—C211.382 (2)
C10—C111.514 (4)C22—N271.341 (2)
C11—O121.459 (2)C22—C231.376 (2)
C11—C151.535 (2)C23—C241.369 (3)
O12—N131.4134 (15)C24—C251.348 (3)
C15—C141.499 (2)C25—C261.372 (3)
C7'—C10'1.686 (18)C26—N271.340 (2)
C10'—C11'1.46 (3)
O5—C1—O2108.04 (15)O12'—C11'—C15'97.2 (9)
C3—O2—C1104.80 (13)N13—O12'—C11'108.3 (6)
C6—C3—C4122.10 (17)C14—C15'—C11'102.6 (6)
C6—C3—O2128.30 (15)C14—N13—O12109.71 (11)
C4—C3—O2109.59 (15)C14—N13—O12'109.71 (11)
C9—C4—C3121.55 (16)N13—C14—C16120.28 (12)
C9—C4—O5128.53 (16)N13—C14—C15'113.37 (13)
C3—C4—O5109.91 (17)C16—C14—C15'126.32 (12)
C4—O5—C1105.10 (14)N13—C14—C15113.37 (13)
C3—C6—C7'117.84 (15)C16—C14—C15126.32 (12)
C3—C6—C7117.84 (15)C17—C16—C21118.06 (13)
C7'—C8—C9122.56 (17)C17—C16—C14120.73 (12)
C7—C8—C9122.56 (17)C21—C16—C14121.19 (13)
C4—C9—C8116.77 (16)C18—C17—C16121.14 (13)
C8—C7—C6119.18 (15)C17—C18—C19121.10 (14)
C8—C7—C10117.97 (16)C20—C19—C18117.77 (14)
C6—C7—C10122.78 (15)C20—C19—C22121.00 (13)
C11—C10—C7116.1 (2)C18—C19—C22121.20 (13)
O12—C11—C10109.52 (19)C21—C20—C19121.29 (13)
O12—C11—C15103.67 (13)C20—C21—C16120.62 (13)
C10—C11—C15114.90 (19)N27—C22—C23121.34 (16)
N13—O12—C11108.16 (10)N27—C22—C19116.55 (14)
C14—C15—C11100.29 (13)C23—C22—C19122.10 (15)
C8—C7'—C6119.18 (15)C24—C23—C22120.60 (18)
C8—C7'—C10'126.6 (6)C25—C24—C23118.6 (2)
C6—C7'—C10'108.8 (7)C24—C25—C26118.5 (2)
C11'—C10'—C7'109.0 (16)N27—C26—C25124.3 (2)
C10'—C11'—O12'110.4 (16)C26—N27—C22116.64 (17)
C10'—C11'—C15'105.5 (16)
O5—C1—O2—C315.6 (2)C10'—C11'—C15'—C14139.5 (13)
C1—O2—C3—C6171.1 (2)O12'—C11'—C15'—C1425.9 (11)
C1—O2—C3—C49.9 (2)C11—O12—N13—C1413.84 (18)
C6—C3—C4—C90.6 (3)C11'—O12'—N13—C1419.5 (9)
O2—C3—C4—C9178.55 (18)O12—N13—C14—C16178.32 (11)
C6—C3—C4—O5179.39 (16)O12'—N13—C14—C16178.32 (11)
O2—C3—C4—O50.3 (2)O12'—N13—C14—C15'0.43 (17)
C9—C4—O5—C1171.8 (2)O12—N13—C14—C150.43 (17)
C3—C4—O5—C19.4 (2)C11'—C15'—C14—N1318.2 (9)
O2—C1—O5—C415.5 (2)C11'—C15'—C14—C16159.6 (8)
C4—C3—C6—C7'0.5 (3)C11—C15—C14—N1313.34 (18)
O2—C3—C6—C7'178.47 (18)C11—C15—C14—C16168.92 (15)
C4—C3—C6—C70.5 (3)N13—C14—C16—C1714.3 (2)
O2—C3—C6—C7178.47 (18)C15'—C14—C16—C17168.09 (14)
C3—C4—C9—C80.7 (3)C15—C14—C16—C17168.09 (14)
O5—C4—C9—C8179.26 (18)N13—C14—C16—C21163.95 (14)
C7'—C8—C9—C40.7 (3)C15'—C14—C16—C2113.6 (2)
C7—C8—C9—C40.7 (3)C15—C14—C16—C2113.6 (2)
C9—C8—C7—C60.7 (3)C21—C16—C17—C180.5 (2)
C9—C8—C7—C10177.9 (2)C14—C16—C17—C18178.82 (12)
C3—C6—C7—C80.5 (3)C16—C17—C18—C191.3 (2)
C3—C6—C7—C10177.6 (2)C17—C18—C19—C200.8 (2)
C8—C7—C10—C11167.2 (2)C17—C18—C19—C22178.84 (13)
C6—C7—C10—C1115.8 (3)C18—C19—C20—C210.4 (2)
C7—C10—C11—O1270.7 (3)C22—C19—C20—C21177.61 (13)
C7—C10—C11—C15173.16 (15)C19—C20—C21—C161.2 (2)
C10—C11—O12—N13144.47 (18)C17—C16—C21—C200.7 (2)
C15—C11—O12—N1321.4 (2)C14—C16—C21—C20177.59 (13)
O12—C11—C15—C1419.99 (19)C20—C19—C22—N2725.0 (2)
C10—C11—C15—C14139.5 (2)C18—C19—C22—N27157.00 (17)
C9—C8—C7'—C60.7 (3)C20—C19—C22—C23154.08 (17)
C9—C8—C7'—C10'150.2 (10)C18—C19—C22—C2323.9 (2)
C3—C6—C7'—C80.5 (3)N27—C22—C23—C241.4 (3)
C3—C6—C7'—C10'155.2 (8)C19—C22—C23—C24177.63 (18)
C8—C7'—C10'—C11'120.6 (13)C22—C23—C24—C250.4 (4)
C6—C7'—C10'—C11'86.1 (16)C23—C24—C25—C260.3 (4)
C7'—C10'—C11'—O12'70 (2)C24—C25—C26—N270.0 (4)
C7'—C10'—C11'—C15'174.2 (9)C25—C26—N27—C221.0 (4)
C10'—C11'—O12'—N13137.7 (14)C23—C22—N27—C261.6 (3)
C15'—C11'—O12'—N1328.1 (12)C19—C22—N27—C26177.46 (18)
 

Acknowledgements

MM thanks UGC, New Delhi, Government of India, for awarding a project under the title F. No. 41–920/2012(SR) dated: 25–07–2012.

References

First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChandra, Raghu, K., Jeyaseelan, S., Umesha, K. B. & Mahendra, M. (2013). Acta Cryst. E69, o987.  CrossRef IUCr Journals Google Scholar
First citationDighade, S., Patil, S., Chincholkar, M. & Dighade, N. (2003). Asian J. Chem. 15, 450–454.  CAS Google Scholar
First citationHabeeb, A. G., Praveen Rao, P. & Knaus, E. E. (2001). J. Med. Chem. 44, 2921–2927.  CrossRef PubMed CAS Google Scholar
First citationKamal, A., Reddy, J. S., Ramaiah, M. J., Dastagiri, D., Bharathi, E. V., Azhar, M. A., Sultana, F., Pushpavalli, S., Pal-Bhadra, M. & Juvekar, A. (2010). Eur. J. Med. Chem. 45, 3924–3937.  CrossRef CAS PubMed Google Scholar
First citationShah, T. & Desai, V. (2007). J. Serb. Chem. Soc. 72, 443–449.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef 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 logoIUCrDATA
ISSN: 2414-3146
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds