research communications
H)-one
and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-phenylpyridazin-3(2aLaboratory of Applied Chemistry and Environment (LCAE), Department of Chemistry, Faculty of Sciences, University Mohamed Premier, Oujda 60000, Morocco, bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey, cLaboratory of Organic Synthesis, Extraction and Development, Faculty of, Sciences, Hassan II University, Casablanca, Morocco, and dLaboratory of Plant Chemistry, Organic and Bioorganic Synthesis, URAC23, Faculty of Science, BP 1014, GEOPAC Research Center, Mohammed V University, Rabat, Morocco
*Correspondence e-mail: elkalifouad408@gmail.com, sevgi.kansiz85@gmail.com
The 17H12Cl2N2O, contains one independent molecule. The molecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2)° and the dichlorophenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)°. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules to form inversion dimers with an R22(8) ring motif. The dimers are linked by C—H⋯O interactions, forming layers parallel to the bc plane. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the molecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H⋯H (31.4%), Cl⋯H/H⋯Cl (19.9%) and C⋯H/H⋯C (19%) contacts.
of the title compound, CKeywords: crystal structure; pyridazin; hydrogen bonding; π–π interactions; Hirshfeld surface analysis.
CCDC reference: 1896404
1. Chemical context
Pyridazinone derivatives are biologically active et al., 2016). Diverse pyridazinone derivatives have been reported to possess a variety of biological activities (Thakur et al. 2010; Asif et al. 2015) such as antimicrobial (Sönmez et al. 2006), anti-inflammatory (Abouzid et al. 2008), analgesic (Gökçe et al. 2009), anti-HIV (Livermore et al. 1993), antihypertensive (Siddiqui et al. 2011), anticonvulsant (Sharma et al. 2014), cardiotonic (Wang et al. 2008), antihistaminic (Tao et al. 2012), antidepressant (Boukharsa et al. 2016), glucan synthase inhibitors (Zhou et al. 2011), phosphodiesterase (PDE) inhibitors (Ochiai et al. 2012) and herbicidal activity (Asif et al. 2013). We report herein the synthesis and the crystal and molecular structures of the title compound, as well as an analysis of its Hirshfeld surfaces.
(Akhtar2. Structural commentary
As the molecular structure of the title compound is illustrated in Fig. 1; the contains one independent molecule. The molecule is not planar, the benzene ring (C12–C17) and the pyridazine ring are twisted relative to each other, making a dihedral angle of 29.96 (2)° and the phenyl ring (C1–C6) is nearly perpendicular to the pyridazine ring with a dihedral angle of 82.38 (11)° (Fig. 1). The C9=O1 bond length is 1.248 (4) Å while the C9—N1 and C11—N2 bond lengths are 1.360 (4) and 1.307 (4) Å, respectively.
3. Supramolecular features
In the crystal, the molecules are linked by a pair of N—H⋯O hydrogen bonds, forming inversion dimers with an (8) ring motif (Table 1 and Fig. 2). The dimers are linked by C—H⋯O hydrogen bonds, forming layers parallel to the bc plane (Fig. 2) and by weak π–π [Cg1⋯Cg3 = 3.839 (2) Å; Cg1 and Cg3 are the centroids of the N1–N2/C9-C11 and C12–C17 rings, respectively] interactions, forming a three-dimensional structure (Fig. 3).
4. Database survey
A search of the Cambridge Structural Database (CSD, version 5.40, update November 2018; Groom et al., 2016) for the 4-phenylpyridazin-3(2H)-one skeleton yielded two hits: 4-benzyl-6-p-tolylpyridazin-3(2H)-one (YOTVIN; Oubair et al., 2009) and ethyl 3-methyl-6-oxo-5-(3-(trifluoromethyl)phenyl)-1,6-dihydro-1-pyridazineacetate (QANVOR; Xu et al., 2005). In YOTVIN, the molecules are connected two by two through N—H⋯O hydrogen bonds with an (8) graph-set motif, building a pseudo dimer arranged about the inversion center (Fig. 4). Weak C—H⋯O hydrogen bonds and weak offset π–π stacking interactions stabilize the packing. In QANVOR, the phenyl and pyridazinone rings are approximately coplanar with a dihedral angle of 4.84 (13)° and in the crystal, centrosymmetrically related molecules form dimers through non-classical intermolecular C—H⋯O hydrogen bonds (Fig. 5).
5. Hirshfeld surface analysis
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007) were performed with CrystalExplorer17 (Turner et al., 2017). In Fig. 6, the mappings of dnorm, shape-index and curvedness for the title compound are shown. Fig. 7 illustrates the Hirshfeld surface of the molecule in the crystal, with the evident hydrogen-bonding interactions indicated by intense red spots.
Fig. 8a shows the two-dimensional fingerprint of the sum of the contacts contributing to the Hirshfeld surface represented in normal mode. Two-dimensional fingerprint plots provide information about the major and minor percentage contributions of interatomic contacts in the compound. The blue colour refers to the frequency of occurrence of the (di, de) pair and the grey colour is the outline of the full fingerprint. The fingerprint plot in Fig. 8b shows that the H⋯H contacts clearly make the most significant contribution to the Hirshfeld surface (31.4%). In addition, Cl⋯H/H⋯Cl, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N contacts contribute 19.9%, 19%, 9.3% and 6.7%, respectively, to the Hirshfeld surface. In particular, the O⋯H/H⋯O contacts indicate the presence of intermolecular N—H⋯O and C—H⋯O interactions. Much weaker Cl⋯C/C⋯Cl (6.1%) and C⋯C (3.7%) contacts also occur.
A view of the molecular electrostatic potential, in the range −0.0500 to 0.0500 a.u. using the 6-31G(d,p) basis set with DFT method, for the title compound is shown in Fig. 9, where the N—H⋯O hydrogen-bond donors and acceptors are shown as blue and red areas around the atoms related with positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials, respectively.
6. Synthesis and crystallization
To a solution (0.15 g, 1 mmol) of 6-phenyl-4,5-dihydropyridazin-3(2H)-one and (0.18 g, 1 mmol) of 2,6-dichlorobenzaldehyde in 30 ml of ethanol, sodium hydroxide 10% (0.5 g, 3.5 mmol) was added. The solvent evaporated under vacuum, the residue was purified through silica gel using hexane/ethyl acetate (7:3 v/v). Single crystals were obtained by slow evaporation at room temperature.
7. Refinement
Crystal data, data collection and structure . The nitrogen-bound H atom was located in a difference-Fourier map and refined subject to a DFIX restraint of N—H = 0.86 Å. The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.93–0.97 Å with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 2Supporting information
CCDC reference: 1896404
https://doi.org/10.1107/S2056989019005139/dx2016sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005139/dx2016Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019005139/dx2016Isup3.cml
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012), SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).C17H12Cl2N2O | F(000) = 680 |
Mr = 331.19 | Dx = 1.423 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8511 (6) Å | Cell parameters from 5578 reflections |
b = 12.5544 (15) Å | θ = 1.9–30.8° |
c = 21.069 (2) Å | µ = 0.42 mm−1 |
β = 92.666 (8)° | T = 296 K |
V = 1546.0 (3) Å3 | Stick, colorless |
Z = 4 | 0.74 × 0.29 × 0.05 mm |
Stoe IPDS 2 diffractometer | 2726 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1196 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.103 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
rotation method scans | h = −6→6 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −14→14 |
Tmin = 0.844, Tmax = 0.973 | l = −25→25 |
8675 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0186P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max < 0.001 |
2726 reflections | Δρmax = 0.15 e Å−3 |
199 parameters | Δρmin = −0.20 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.0717 (2) | 0.77603 (11) | 0.74856 (7) | 0.1004 (5) | |
Cl2 | 0.5870 (2) | 0.47508 (11) | 0.76181 (7) | 0.1022 (5) | |
O1 | −0.0083 (5) | 0.4872 (2) | 0.58329 (11) | 0.0681 (9) | |
N1 | 0.2647 (5) | 0.5706 (3) | 0.52916 (14) | 0.0543 (9) | |
H1 | 0.215035 | 0.536383 | 0.495963 | 0.065* | |
N2 | 0.4383 (5) | 0.6397 (3) | 0.52057 (14) | 0.0497 (8) | |
C11 | 0.5192 (6) | 0.6884 (3) | 0.57161 (17) | 0.0455 (10) | |
C9 | 0.1594 (7) | 0.5487 (3) | 0.58387 (18) | 0.0502 (11) | |
C12 | 0.7076 (6) | 0.7653 (3) | 0.56287 (18) | 0.0486 (10) | |
C8 | 0.2566 (7) | 0.6008 (3) | 0.63964 (16) | 0.0481 (10) | |
C10 | 0.4302 (6) | 0.6696 (3) | 0.63241 (18) | 0.0500 (10) | |
H10 | 0.492982 | 0.705353 | 0.667723 | 0.060* | |
C6 | 0.2580 (7) | 0.6252 (4) | 0.75974 (16) | 0.0496 (10) | |
C13 | 0.8619 (7) | 0.7518 (3) | 0.51557 (18) | 0.0547 (11) | |
H13 | 0.844994 | 0.694576 | 0.487703 | 0.066* | |
C1 | 0.1647 (7) | 0.7164 (4) | 0.78577 (18) | 0.0552 (11) | |
C5 | 0.4515 (7) | 0.5861 (3) | 0.79161 (19) | 0.0587 (11) | |
C7 | 0.1522 (7) | 0.5726 (3) | 0.70160 (16) | 0.0644 (12) | |
H7A | −0.008906 | 0.591153 | 0.698375 | 0.077* | |
H7B | 0.162232 | 0.496083 | 0.707307 | 0.077* | |
C17 | 0.7339 (7) | 0.8532 (4) | 0.60200 (19) | 0.0635 (12) | |
H17 | 0.627740 | 0.865436 | 0.632688 | 0.076* | |
C14 | 1.0395 (7) | 0.8220 (4) | 0.5094 (2) | 0.0652 (13) | |
H14 | 1.141541 | 0.812120 | 0.477372 | 0.078* | |
C2 | 0.2559 (8) | 0.7640 (4) | 0.8395 (2) | 0.0697 (13) | |
H2 | 0.188409 | 0.824841 | 0.855430 | 0.084* | |
C15 | 1.0671 (8) | 0.9066 (4) | 0.5503 (2) | 0.0699 (13) | |
H15 | 1.189954 | 0.952831 | 0.546718 | 0.084* | |
C4 | 0.5475 (8) | 0.6332 (5) | 0.8459 (2) | 0.0791 (15) | |
H4 | 0.678943 | 0.604863 | 0.865828 | 0.095* | |
C16 | 0.9128 (8) | 0.9230 (4) | 0.5967 (2) | 0.0724 (13) | |
H16 | 0.929468 | 0.980734 | 0.624227 | 0.087* | |
C3 | 0.4477 (9) | 0.7215 (5) | 0.8698 (2) | 0.0859 (16) | |
H3 | 0.509354 | 0.753135 | 0.906685 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0858 (9) | 0.0865 (10) | 0.1269 (11) | 0.0090 (8) | −0.0179 (8) | 0.0212 (9) |
Cl2 | 0.1090 (11) | 0.0865 (10) | 0.1149 (10) | 0.0230 (9) | 0.0478 (8) | 0.0115 (9) |
O1 | 0.083 (2) | 0.074 (2) | 0.0473 (16) | −0.0306 (18) | −0.0006 (15) | −0.0049 (16) |
N1 | 0.071 (2) | 0.053 (2) | 0.039 (2) | −0.007 (2) | −0.0005 (18) | −0.0096 (17) |
N2 | 0.055 (2) | 0.052 (2) | 0.0420 (19) | −0.0023 (18) | 0.0037 (16) | −0.0009 (17) |
C11 | 0.049 (2) | 0.053 (3) | 0.034 (2) | 0.003 (2) | −0.0035 (19) | −0.002 (2) |
C9 | 0.061 (3) | 0.048 (3) | 0.041 (2) | −0.002 (2) | 0.002 (2) | 0.001 (2) |
C12 | 0.053 (2) | 0.050 (3) | 0.043 (2) | −0.004 (2) | −0.001 (2) | 0.005 (2) |
C8 | 0.058 (2) | 0.056 (3) | 0.030 (2) | −0.005 (2) | −0.0010 (19) | −0.003 (2) |
C10 | 0.058 (3) | 0.055 (3) | 0.037 (2) | −0.011 (2) | −0.002 (2) | −0.002 (2) |
C6 | 0.058 (3) | 0.061 (3) | 0.031 (2) | −0.016 (2) | 0.008 (2) | 0.000 (2) |
C13 | 0.057 (2) | 0.061 (3) | 0.046 (2) | −0.002 (2) | 0.004 (2) | 0.004 (2) |
C1 | 0.063 (3) | 0.061 (3) | 0.042 (2) | −0.012 (2) | 0.004 (2) | 0.003 (2) |
C5 | 0.059 (3) | 0.067 (3) | 0.051 (3) | −0.001 (2) | 0.016 (2) | 0.008 (2) |
C7 | 0.082 (3) | 0.066 (3) | 0.046 (2) | −0.022 (3) | 0.010 (2) | −0.004 (2) |
C17 | 0.068 (3) | 0.070 (3) | 0.053 (3) | −0.016 (3) | 0.014 (2) | −0.008 (3) |
C14 | 0.055 (3) | 0.076 (4) | 0.066 (3) | 0.007 (3) | 0.016 (2) | 0.015 (3) |
C2 | 0.091 (3) | 0.066 (3) | 0.053 (3) | −0.008 (3) | 0.014 (3) | −0.011 (3) |
C15 | 0.066 (3) | 0.071 (4) | 0.073 (3) | −0.014 (3) | 0.010 (3) | 0.008 (3) |
C4 | 0.069 (3) | 0.114 (5) | 0.053 (3) | −0.004 (3) | −0.009 (3) | 0.011 (3) |
C16 | 0.082 (3) | 0.068 (3) | 0.068 (3) | −0.019 (3) | 0.012 (3) | −0.008 (3) |
C3 | 0.098 (4) | 0.117 (5) | 0.043 (3) | −0.020 (4) | 0.003 (3) | −0.006 (3) |
Cl1—C1 | 1.729 (4) | C13—C14 | 1.373 (5) |
Cl2—C5 | 1.735 (4) | C13—H13 | 0.9300 |
O1—C9 | 1.248 (4) | C1—C2 | 1.366 (5) |
N1—N2 | 1.354 (4) | C5—C4 | 1.383 (5) |
N1—C9 | 1.360 (4) | C7—H7A | 0.9700 |
N1—H1 | 0.8600 | C7—H7B | 0.9700 |
N2—C11 | 1.307 (4) | C17—C16 | 1.373 (5) |
C11—C10 | 1.425 (5) | C17—H17 | 0.9300 |
C11—C12 | 1.483 (5) | C14—C15 | 1.373 (5) |
C9—C8 | 1.438 (5) | C14—H14 | 0.9300 |
C12—C17 | 1.382 (5) | C2—C3 | 1.373 (6) |
C12—C13 | 1.386 (5) | C2—H2 | 0.9300 |
C8—C10 | 1.348 (5) | C15—C16 | 1.377 (6) |
C8—C7 | 1.509 (5) | C15—H15 | 0.9300 |
C10—H10 | 0.9300 | C4—C3 | 1.361 (6) |
C6—C5 | 1.380 (5) | C4—H4 | 0.9300 |
C6—C1 | 1.391 (5) | C16—H16 | 0.9300 |
C6—C7 | 1.500 (5) | C3—H3 | 0.9300 |
N2—N1—C9 | 128.0 (3) | C6—C5—Cl2 | 119.2 (3) |
N2—N1—H1 | 116.0 | C4—C5—Cl2 | 117.9 (4) |
C9—N1—H1 | 116.0 | C6—C7—C8 | 115.8 (3) |
C11—N2—N1 | 115.8 (3) | C6—C7—H7A | 108.3 |
N2—C11—C10 | 121.9 (4) | C8—C7—H7A | 108.3 |
N2—C11—C12 | 116.4 (4) | C6—C7—H7B | 108.3 |
C10—C11—C12 | 121.7 (3) | C8—C7—H7B | 108.3 |
O1—C9—N1 | 120.3 (3) | H7A—C7—H7B | 107.4 |
O1—C9—C8 | 124.7 (4) | C16—C17—C12 | 121.7 (4) |
N1—C9—C8 | 115.0 (4) | C16—C17—H17 | 119.1 |
C17—C12—C13 | 117.9 (4) | C12—C17—H17 | 119.1 |
C17—C12—C11 | 120.6 (4) | C13—C14—C15 | 120.3 (4) |
C13—C12—C11 | 121.5 (4) | C13—C14—H14 | 119.9 |
C10—C8—C9 | 118.1 (4) | C15—C14—H14 | 119.9 |
C10—C8—C7 | 125.8 (3) | C1—C2—C3 | 119.7 (5) |
C9—C8—C7 | 116.1 (4) | C1—C2—H2 | 120.2 |
C8—C10—C11 | 121.2 (3) | C3—C2—H2 | 120.2 |
C8—C10—H10 | 119.4 | C14—C15—C16 | 120.0 (4) |
C11—C10—H10 | 119.4 | C14—C15—H15 | 120.0 |
C5—C6—C1 | 115.4 (3) | C16—C15—H15 | 120.0 |
C5—C6—C7 | 122.6 (4) | C3—C4—C5 | 119.3 (4) |
C1—C6—C7 | 122.0 (4) | C3—C4—H4 | 120.3 |
C14—C13—C12 | 120.7 (4) | C5—C4—H4 | 120.3 |
C14—C13—H13 | 119.6 | C17—C16—C15 | 119.3 (4) |
C12—C13—H13 | 119.6 | C17—C16—H16 | 120.4 |
C2—C1—C6 | 122.8 (4) | C15—C16—H16 | 120.4 |
C2—C1—Cl1 | 117.4 (4) | C4—C3—C2 | 120.0 (4) |
C6—C1—Cl1 | 119.9 (3) | C4—C3—H3 | 120.0 |
C6—C5—C4 | 122.8 (4) | C2—C3—H3 | 120.0 |
C9—N1—N2—C11 | 2.6 (5) | C7—C6—C1—Cl1 | −3.3 (5) |
N1—N2—C11—C10 | 0.1 (5) | C1—C6—C5—C4 | 0.2 (6) |
N1—N2—C11—C12 | −179.3 (3) | C7—C6—C5—C4 | −178.8 (4) |
N2—N1—C9—O1 | 175.7 (3) | C1—C6—C5—Cl2 | −178.0 (3) |
N2—N1—C9—C8 | −4.5 (6) | C7—C6—C5—Cl2 | 2.9 (5) |
N2—C11—C12—C17 | 149.5 (4) | C5—C6—C7—C8 | −83.4 (5) |
C10—C11—C12—C17 | −29.9 (5) | C1—C6—C7—C8 | 97.5 (5) |
N2—C11—C12—C13 | −30.4 (5) | C10—C8—C7—C6 | −1.5 (6) |
C10—C11—C12—C13 | 150.1 (4) | C9—C8—C7—C6 | 178.6 (4) |
O1—C9—C8—C10 | −176.5 (4) | C13—C12—C17—C16 | −3.0 (6) |
N1—C9—C8—C10 | 3.7 (5) | C11—C12—C17—C16 | 177.1 (4) |
O1—C9—C8—C7 | 3.5 (6) | C12—C13—C14—C15 | 0.2 (6) |
N1—C9—C8—C7 | −176.4 (4) | C6—C1—C2—C3 | 0.1 (6) |
C9—C8—C10—C11 | −1.5 (6) | Cl1—C1—C2—C3 | −178.1 (4) |
C7—C8—C10—C11 | 178.5 (4) | C13—C14—C15—C16 | −1.7 (6) |
N2—C11—C10—C8 | −0.5 (6) | C6—C5—C4—C3 | 0.6 (7) |
C12—C11—C10—C8 | 179.0 (4) | Cl2—C5—C4—C3 | 178.8 (4) |
C17—C12—C13—C14 | 2.1 (6) | C12—C17—C16—C15 | 1.6 (6) |
C11—C12—C13—C14 | −178.0 (3) | C14—C15—C16—C17 | 0.9 (7) |
C5—C6—C1—C2 | −0.6 (6) | C5—C4—C3—C2 | −1.1 (7) |
C7—C6—C1—C2 | 178.5 (4) | C1—C2—C3—C4 | 0.8 (7) |
C5—C6—C1—Cl1 | 177.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.04 | 2.839 (4) | 155 |
C2—H2···O1ii | 0.93 | 2.66 | 3.581 (6) | 172 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y+1/2, −z+3/2. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).
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