organic compounds
3-(4-Chlorophenyl)-5-[4-(methylsulfanyl)phenyl]-1H-pyrazole
aDepartment of Chemistry, Ramakrishna Mission Vivekananda College, Chennai 600 004, India
*Correspondence e-mail: muniraj_sl@yahoo.com
In the title compound, C16H13ClN2S, the pyrazole ring is almost planar with an r.m.s. deviation of 0.0457 Å which forms dihedral angles of 2.875 (4) and 84.83 (7)° with the chloro-substituted benzene ring and the methylsulfanyl-substituted ring, respectively. In the crystal, N—H⋯N and C—H⋯Cl hydrogen bonds contribute to the formation of a three-dimensional network. In addition, several offset π–π stacking interactions are also present.
Keywords: crystal structure; pyrazole; chalcone; isoniazid; conformations.
CCDC reference: 1453871
Structure description
Pyrazoles (Kamatchi et al., 2012) exhibit a variety of pharmacological properties including antibacterial and anti-inflammatory activities (Sullivan et al., 2006; Patel et al., 2010). A pyrazole derivative also shows nucleosidase inhibitory activity against Staphylococcus aureus (Siu et al. 2008). In view of their importance, we have synthesized the title pyrazole derivative and its is reported here.
The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring (N1/N2/C7–C9) is almost planar with an r.m.s deviation of 0.0457 Å. This ring subtends a dihedral angle of 2.875 (4)° with the chloro-substituted benzene ring (C12–C17) while the C1–C6 benzene ring is almost perpendicular to the pyrazole ring with a dihedral angle 84.83 (7)°.
In the crystal, centrosymmetrically related N1—H1⋯N2 hydrogen bonds (Table 1) form inversion dimers with R22(6) ring motifs. Furthermore, as shown in Fig. 2, molecules are linked in a head-to-tail fashion by π–π stacking interactions with centroid–centroid distances Cg1⋯Cg1iii = 3.538 (2) and Cg2⋯Cg3iii = 3.8610 (18) Å [Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C7–C9, C1–C6 and C12–C17 rings, respectively; symmetry code: (iii) −x + 2, −y + 1, −z + 1]. In addition to the N1—H1⋯N1 hydrogen bonds, there are also weak but effective C14—H14⋯Cl1 hydrogen bonds that also contribute to the formation of a three-dimensional network (Fig. 3).
Synthesis and crystallization
A mixture of substituted chalcone (0.01 mol) and isoniazid (0.01 mol) kept in 25 ml round bottom flask then heated for 160°C for 1 h. The reaction mixture was cooled and purified by
The purified compound was recrystallized from hexane/ethylacetate (3:6) by the slow evaporation method.Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1453871
10.1107/S2414314616006799/sj4019sup1.cif
contains datablocks I, 2R. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006799/sj4019Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006799/sj4019Isup3.cml
A mixture of substituted chalcone (0.01 mol) and isoniazid (0.01 mol) kept in 25 ml round bottom flask then heated for 160°C 1h. The reaction mixture was cooled and purified by
The purified compound was recrystallized from hexane/ethylacetate (3:6) by the slow evaporation method.A mixture of substituted chalcone (0.01 mol) and isoniazid (0.01 mol) kept in 25 ml round bottom flask then heated for 160°C for 1 h. The reaction mixture was cooled and purified by
The purified compound was recrystallized from hexane/ethylacetate (3:6) by the slow evaporation method.Pyrazoles (Kamatchi et al., 2012) exhibit a variety of pharmacological properties including antibacterial and anti-inflammatory activities (Sullivan et al., 2006; Patel et al., 2010). A pyrazole derivative also shows nucleosidase inhibitory activity against Staphylococcus aureus (Siu et al. 2008). In view of their importance, we have synthesized the title pyrazole derivative and its
is reported here.The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring (N1/N2/C7–C9) is almost planar with an r.m.s deviation of 0.0457 Å. This ring subtends a dihedral angle of 2.875 (4)° with the chloro-substituted benzene ring (C12–C17) while the C1–C6 benzene ring is almost perpendicular to the pyrazole ring with a dihedral angle 84.83 (7)°.
In the crystal, centrosymmetrically related N1—H1···N2 hydrogen bonds (Table 1) form inversion dimers with R22(6) ring motifs. Furthermore, as shown in Fig. 2, molecules are linked in a head-to-tail fashion by π–π stacking interactions with centroid–centroid distances Cg1···Cg1iii = 3.538 (2) and Cg2···Cg3iii = 3.8610 (18) Å [Cg1, Cg2 and Cg3 are the centroids of the N1/N2/C7–C9, C1–C6 and C12–C17 rings, respectively; symmetry code: (iii) -x + 2, -y + 1, -z + 1]. In addition to the N1—H1···N1 hydrogen bonds, there are also weak but effective C14—H14···Cl1 hydrogen bonds that also contribute to the formation of a three-dimensional network (Fig. 3).
Data collection: APEX2 (Bruker, 2012); cell
APEX2 and SAINT (Bruker, 2012); data reduction: SAINT and XPREP (Bruker, 2012); 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, 2012); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. | |
Fig. 2. π–π stacking interactions shown as dotted green lines with ring centroids displayed as coloured spheres. For centroid labels and symmetry operations see text. | |
Fig. 3. The crystal packing of the title compound, viewed along the a axis. |
C16H13ClN2S | F(000) = 624 |
Mr = 300.79 | Dx = 1.412 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.0422 (12) Å | Cell parameters from 8419 reflections |
b = 5.6323 (5) Å | θ = 2.8–30.1° |
c = 17.1019 (15) Å | µ = 0.41 mm−1 |
β = 102.480 (2)° | T = 296 K |
V = 1414.7 (2) Å3 | Block, pale-yellow |
Z = 4 | 0.25 × 0.25 × 0.15 mm |
Bruker Kappa APEXII CCD diffractometer | 2921 independent reflections |
Radiation source: fine-focus sealed tube | 2210 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scan | θmax = 26.5°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −18→18 |
Tmin = 0.905, Tmax = 0.941 | k = −7→7 |
20565 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0259P)2 + 2.3699P] where P = (Fo2 + 2Fc2)/3 |
2921 reflections | (Δ/σ)max < 0.001 |
186 parameters | Δρmax = 0.40 e Å−3 |
1 restraint | Δρmin = −0.28 e Å−3 |
C16H13ClN2S | V = 1414.7 (2) Å3 |
Mr = 300.79 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.0422 (12) Å | µ = 0.41 mm−1 |
b = 5.6323 (5) Å | T = 296 K |
c = 17.1019 (15) Å | 0.25 × 0.25 × 0.15 mm |
β = 102.480 (2)° |
Bruker Kappa APEXII CCD diffractometer | 2921 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 2210 reflections with I > 2σ(I) |
Tmin = 0.905, Tmax = 0.941 | Rint = 0.033 |
20565 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 1 restraint |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.40 e Å−3 |
2921 reflections | Δρmin = −0.28 e Å−3 |
186 parameters |
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. |
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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.86308 (19) | 0.4265 (5) | 0.14839 (17) | 0.0358 (7) | |
C2 | 0.8308 (2) | 0.6014 (6) | 0.19216 (18) | 0.0391 (7) | |
H2 | 0.8035 | 0.7364 | 0.1662 | 0.047* | |
C3 | 0.83852 (19) | 0.5781 (5) | 0.27367 (18) | 0.0367 (7) | |
H3 | 0.8165 | 0.6974 | 0.3019 | 0.044* | |
C4 | 0.87890 (18) | 0.3781 (5) | 0.31398 (16) | 0.0311 (6) | |
C5 | 0.9089 (2) | 0.2024 (5) | 0.26987 (18) | 0.0389 (7) | |
H5 | 0.9345 | 0.0652 | 0.2956 | 0.047* | |
C6 | 0.9017 (2) | 0.2257 (6) | 0.18792 (18) | 0.0417 (7) | |
H6 | 0.9230 | 0.1054 | 0.1595 | 0.050* | |
C7 | 0.88814 (18) | 0.3566 (5) | 0.40110 (17) | 0.0332 (6) | |
C8 | 0.85749 (19) | 0.5015 (5) | 0.45494 (17) | 0.0352 (6) | |
H8 | 0.8232 | 0.6395 | 0.4433 | 0.042* | |
C9 | 0.88822 (18) | 0.3997 (5) | 0.53004 (17) | 0.0327 (6) | |
C12 | 0.87854 (18) | 0.4797 (5) | 0.60968 (16) | 0.0321 (6) | |
C13 | 0.8377 (2) | 0.6961 (5) | 0.61894 (18) | 0.0388 (7) | |
H13 | 0.8159 | 0.7904 | 0.5743 | 0.047* | |
C14 | 0.8292 (2) | 0.7730 (6) | 0.69368 (19) | 0.0438 (8) | |
H14 | 0.8008 | 0.9170 | 0.6990 | 0.053* | |
C15 | 0.8623 (2) | 0.6378 (6) | 0.75962 (18) | 0.0404 (7) | |
C16 | 0.9032 (2) | 0.4230 (6) | 0.75310 (19) | 0.0450 (8) | |
H16 | 0.9255 | 0.3313 | 0.7983 | 0.054* | |
C17 | 0.9107 (2) | 0.3454 (6) | 0.67792 (18) | 0.0417 (7) | |
H17 | 0.9379 | 0.1995 | 0.6731 | 0.050* | |
C20 | 0.8972 (3) | 0.2228 (8) | 0.0090 (2) | 0.0764 (13) | |
H20A | 0.9598 | 0.2052 | 0.0360 | 0.115* | |
H20B | 0.8934 | 0.2383 | −0.0475 | 0.115* | |
H20C | 0.8634 | 0.0857 | 0.0190 | 0.115* | |
N1 | 0.93368 (18) | 0.1756 (5) | 0.44264 (16) | 0.0426 (6) | |
N2 | 0.93436 (17) | 0.2002 (5) | 0.52172 (15) | 0.0422 (6) | |
S1 | 0.85099 (7) | 0.48113 (18) | 0.04526 (5) | 0.0577 (3) | |
Cl1 | 0.85408 (7) | 0.74040 (19) | 0.85373 (5) | 0.0638 (3) | |
H1 | 0.974 (3) | 0.066 (8) | 0.437 (3) | 0.17 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0343 (15) | 0.0373 (17) | 0.0360 (16) | −0.0041 (13) | 0.0079 (12) | −0.0013 (13) |
C2 | 0.0395 (17) | 0.0340 (16) | 0.0435 (17) | 0.0051 (14) | 0.0081 (13) | 0.0062 (14) |
C3 | 0.0380 (16) | 0.0308 (15) | 0.0421 (17) | 0.0060 (13) | 0.0104 (13) | −0.0015 (13) |
C4 | 0.0261 (13) | 0.0312 (15) | 0.0358 (15) | −0.0011 (12) | 0.0065 (11) | −0.0002 (12) |
C5 | 0.0428 (17) | 0.0288 (15) | 0.0441 (17) | 0.0051 (13) | 0.0077 (13) | 0.0006 (13) |
C6 | 0.0477 (18) | 0.0334 (16) | 0.0453 (18) | 0.0039 (14) | 0.0130 (14) | −0.0058 (14) |
C7 | 0.0279 (14) | 0.0312 (15) | 0.0400 (16) | −0.0002 (12) | 0.0062 (12) | 0.0033 (13) |
C8 | 0.0346 (15) | 0.0316 (15) | 0.0392 (15) | 0.0053 (13) | 0.0079 (12) | 0.0020 (13) |
C9 | 0.0298 (14) | 0.0305 (15) | 0.0388 (16) | −0.0009 (12) | 0.0094 (12) | −0.0005 (12) |
C12 | 0.0280 (14) | 0.0321 (15) | 0.0371 (15) | −0.0008 (12) | 0.0090 (12) | 0.0023 (12) |
C13 | 0.0415 (17) | 0.0351 (16) | 0.0405 (16) | 0.0090 (14) | 0.0101 (13) | 0.0057 (13) |
C14 | 0.0461 (18) | 0.0363 (17) | 0.0514 (19) | 0.0069 (15) | 0.0162 (15) | −0.0022 (15) |
C15 | 0.0390 (17) | 0.0445 (18) | 0.0396 (16) | −0.0067 (15) | 0.0130 (13) | −0.0031 (14) |
C16 | 0.0510 (19) | 0.0459 (19) | 0.0379 (17) | 0.0032 (16) | 0.0092 (14) | 0.0088 (14) |
C17 | 0.0460 (18) | 0.0335 (17) | 0.0472 (18) | 0.0081 (14) | 0.0138 (14) | 0.0062 (14) |
C20 | 0.099 (3) | 0.087 (3) | 0.045 (2) | 0.019 (3) | 0.021 (2) | −0.013 (2) |
N1 | 0.0458 (16) | 0.0394 (15) | 0.0428 (15) | 0.0111 (13) | 0.0097 (12) | 0.0059 (12) |
N2 | 0.0468 (15) | 0.0370 (14) | 0.0452 (15) | 0.0090 (12) | 0.0154 (12) | 0.0016 (12) |
S1 | 0.0807 (7) | 0.0554 (6) | 0.0372 (5) | 0.0033 (5) | 0.0128 (4) | 0.0001 (4) |
Cl1 | 0.0752 (6) | 0.0743 (7) | 0.0446 (5) | −0.0040 (5) | 0.0188 (4) | −0.0161 (5) |
C1—C6 | 1.380 (4) | C12—C17 | 1.387 (4) |
C1—C2 | 1.387 (4) | C12—C13 | 1.389 (4) |
C1—S1 | 1.761 (3) | C13—C14 | 1.382 (4) |
C2—C3 | 1.380 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.363 (4) |
C3—C4 | 1.390 (4) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C16 | 1.372 (5) |
C4—C5 | 1.378 (4) | C15—Cl1 | 1.740 (3) |
C4—C7 | 1.471 (4) | C16—C17 | 1.385 (4) |
C5—C6 | 1.388 (4) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—H6 | 0.9300 | C20—S1 | 1.781 (4) |
C7—N1 | 1.343 (4) | C20—H20A | 0.9600 |
C7—C8 | 1.382 (4) | C20—H20B | 0.9600 |
C8—C9 | 1.391 (4) | C20—H20C | 0.9600 |
C8—H8 | 0.9300 | N1—N2 | 1.357 (4) |
C9—N2 | 1.344 (4) | N1—H1 | 0.891 (10) |
C9—C12 | 1.471 (4) | ||
C6—C1—C2 | 118.5 (3) | C17—C12—C9 | 121.7 (3) |
C6—C1—S1 | 125.1 (2) | C13—C12—C9 | 120.6 (3) |
C2—C1—S1 | 116.4 (2) | C14—C13—C12 | 120.8 (3) |
C3—C2—C1 | 121.0 (3) | C14—C13—H13 | 119.6 |
C3—C2—H2 | 119.5 | C12—C13—H13 | 119.6 |
C1—C2—H2 | 119.5 | C15—C14—C13 | 120.0 (3) |
C2—C3—C4 | 120.7 (3) | C15—C14—H14 | 120.0 |
C2—C3—H3 | 119.6 | C13—C14—H14 | 120.0 |
C4—C3—H3 | 119.6 | C14—C15—C16 | 121.1 (3) |
C5—C4—C3 | 118.0 (3) | C14—C15—Cl1 | 119.5 (3) |
C5—C4—C7 | 121.6 (3) | C16—C15—Cl1 | 119.4 (2) |
C3—C4—C7 | 120.3 (3) | C15—C16—C17 | 118.8 (3) |
C4—C5—C6 | 121.4 (3) | C15—C16—H16 | 120.6 |
C4—C5—H5 | 119.3 | C17—C16—H16 | 120.6 |
C6—C5—H5 | 119.3 | C16—C17—C12 | 121.7 (3) |
C1—C6—C5 | 120.3 (3) | C16—C17—H17 | 119.2 |
C1—C6—H6 | 119.8 | C12—C17—H17 | 119.2 |
C5—C6—H6 | 119.8 | S1—C20—H20A | 109.5 |
N1—C7—C8 | 107.5 (3) | S1—C20—H20B | 109.5 |
N1—C7—C4 | 121.6 (3) | H20A—C20—H20B | 109.5 |
C8—C7—C4 | 130.8 (3) | S1—C20—H20C | 109.5 |
C7—C8—C9 | 106.2 (3) | H20A—C20—H20C | 109.5 |
C7—C8—H8 | 126.9 | H20B—C20—H20C | 109.5 |
C9—C8—H8 | 126.9 | C7—N1—N2 | 110.0 (3) |
N2—C9—C8 | 108.8 (3) | C7—N1—H1 | 139 (4) |
N2—C9—C12 | 120.7 (3) | N2—N1—H1 | 109 (4) |
C8—C9—C12 | 130.4 (3) | C9—N2—N1 | 107.3 (2) |
C17—C12—C13 | 117.7 (3) | C1—S1—C20 | 104.04 (17) |
C6—C1—C2—C3 | 1.2 (4) | N2—C9—C12—C13 | 174.4 (3) |
S1—C1—C2—C3 | −178.8 (2) | C8—C9—C12—C13 | −4.2 (5) |
C1—C2—C3—C4 | −0.1 (5) | C17—C12—C13—C14 | −0.4 (4) |
C2—C3—C4—C5 | −1.5 (4) | C9—C12—C13—C14 | −179.4 (3) |
C2—C3—C4—C7 | 179.0 (3) | C12—C13—C14—C15 | 1.1 (5) |
C3—C4—C5—C6 | 1.8 (4) | C13—C14—C15—C16 | −1.0 (5) |
C7—C4—C5—C6 | −178.7 (3) | C13—C14—C15—Cl1 | 178.2 (2) |
C2—C1—C6—C5 | −0.9 (4) | C14—C15—C16—C17 | 0.3 (5) |
S1—C1—C6—C5 | 179.1 (2) | Cl1—C15—C16—C17 | −178.9 (2) |
C4—C5—C6—C1 | −0.7 (5) | C15—C16—C17—C12 | 0.4 (5) |
C5—C4—C7—N1 | 6.3 (4) | C13—C12—C17—C16 | −0.4 (4) |
C3—C4—C7—N1 | −174.2 (3) | C9—C12—C17—C16 | 178.7 (3) |
C5—C4—C7—C8 | −174.9 (3) | C8—C7—N1—N2 | −0.7 (3) |
C3—C4—C7—C8 | 4.6 (5) | C4—C7—N1—N2 | 178.4 (2) |
N1—C7—C8—C9 | 0.9 (3) | C8—C9—N2—N1 | 0.4 (3) |
C4—C7—C8—C9 | −178.0 (3) | C12—C9—N2—N1 | −178.5 (2) |
C7—C8—C9—N2 | −0.8 (3) | C7—N1—N2—C9 | 0.2 (3) |
C7—C8—C9—C12 | 178.0 (3) | C6—C1—S1—C20 | 0.9 (3) |
N2—C9—C12—C17 | −4.6 (4) | C2—C1—S1—C20 | −179.1 (3) |
C8—C9—C12—C17 | 176.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cl1i | 0.93 | 2.94 | 3.771 (3) | 149 |
N1—H1···N2ii | 0.89 (1) | 2.05 (3) | 2.875 (4) | 153 (5) |
N1—H1···N1ii | 0.89 (1) | 2.61 (5) | 3.170 (5) | 122 (4) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+2, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cl1i | 0.93 | 2.94 | 3.771 (3) | 149.3 |
N1—H1···N2ii | 0.891 (10) | 2.05 (3) | 2.875 (4) | 153 (5) |
N1—H1···N1ii | 0.891 (10) | 2.61 (5) | 3.170 (5) | 122 (4) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H13ClN2S |
Mr | 300.79 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 15.0422 (12), 5.6323 (5), 17.1019 (15) |
β (°) | 102.480 (2) |
V (Å3) | 1414.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.25 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2012) |
Tmin, Tmax | 0.905, 0.941 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20565, 2921, 2210 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.130, 1.12 |
No. of reflections | 2921 |
No. of parameters | 186 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.28 |
Computer programs: APEX2 (Bruker, 2012), APEX2 and SAINT (Bruker, 2012), SAINT and XPREP (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).
Acknowledgements
The authors are very grateful to staff members of the Department of Chemistry, Ramakrishna Mission Vivekananda College, Mylapore, and Chennai. They also thank the Sophisticated Analytical Instrumentation Facility (SAIF), IIT Madras, for analytical support. GS thanks the CSIR for an SRF grant [No. 08/508 (0001)/2013-EMR-I].
References
Bruker (2012). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kamatchi, P., Jagadeesan, G., Pramesh, M., Perumal, P. T. & Aravindhan, S. (2012). Acta Cryst. E68, o552. CrossRef IUCr Journals Google Scholar
Patel, C. K., Rami, C. S., Panigrahi, B. & Patel, C. N. (2010). J. Chem. Pharm. Res. 2, 73–78. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siu, K. K. W., Lee, J. E., Smith, G. D., Horvatin-Mrakovcic, C. & Howell, P. L. (2008). Acta Cryst. F64, 343–350. 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
Sullivan, T. J., Truglio, J. J., Boyne, M. E., Novichenok, P., Zhang, X., Stratton, C. F., Li, H., Kaur, T., Amin, A., Johnson, F., Slayden, R. A., Kisker, C. & Tonge, P. J. (2006). Chem. Biol. 1, 43–53. CAS Google Scholar
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