research communications
Synthesis, N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide
and Hirshfeld surface analysis ofaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India, bDepartment of Science and Humanities, PES University, BSK III Stage, Bengaluru-560 085, India, cDepartment of Chemistry, Amrita School of Engineering, Amrita Vishwa Vidyapeetham, Bengaluru-560 035, India, dHoneychem Pharma Research Pvt. Ltd., Peenya Industrial Area, Bengaluru-560 058, India, and eDepartment of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA
*Correspondence e-mail: ybb2706@gmail.com, yathirajan@hotmail.com
The synthesis and 12H16FNO3S, which is related to the herbicide flufenacet, are presented. The dihedral angle between the amide group and the fluorinated benzene ring is 87.30 (5)° and the N—C—C—S torsion angle defining the orientation of the methylsulfonyl substituent relative to the amide group is 106.91 (11)°. In the crystal, inversion-related molecules form dimers as a result of pairwise C—H⋯O hydrogen bonds, which appear to be reinforced by short O⋯π contacts [O⋯Cg = 3.0643 (11) Å]. A Hirshfeld surface analysis was used to quantify the various types of intermolecular contacts, which are dominated by H atoms.
of the title compound, CKeywords: N-(substituted phenyl)acetamide; flufenacet metabolite; crystal structure; Hirshfeld surface analysis.
CCDC reference: 2258160
1. Chemical context
N-(Substituted phenyl)acetamides have a variety of biological activities. For example, substituted phenylacetamides and their use as protease inhibitors was reported by Kreutter et al. (2009) and a description of the syntheses and antioxidant studies of N-substituted benzyl/phenyl-2-[3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl]acetamides was given by Ahmad et al. (2013). The syntheses and biological evaluation of N4-substituted sulfonamide–acetamide derivatives as dihydrofolate reductase (DHFR) inhibitors was reported by Hussein et al. (2019) and the synthesis of N-(substituted phenyl)-N-(substituted)acetamide derivatives as potent analgesic agents was described by Verma et al. (2020). Lastly, the evaluation of new 2-hydroxy-N-(4-oxo-2-substituted phenyl-1,3-thiazolidin-3-yl)-2-phenylacetamide derivatives as potential antimycobacterial agents was reported by Güzel-Akdemir et al. (2020).
Flufenacet (C14H13F4N3O2S), N-(4-fluorophenyl)-N-propan-2-yl-2-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}acetamide, is an herbicide, xenobiotic and environmental contaminant (Rouchaud et al., 2001; Zimmerman et al., 2002). This paper reports the synthesis, and a Hirshfeld surface analysis of the related title compound, C12H16FNO3S (I) (Fig. 1).
2. Structural commentary
In the I, the nitrogen atom of the amide group is close to planar, the sum of bond angles about N1 being 358.92 (19)°, which places N1 0.0862 (14) Å from the plane passing through C1, C4, and C7. The amide group is also almost planar, having an r.m.s. deviation from the mean plane of N1, C1, O1, C2 of 0.0095 Å [maximum = 0.0165 (11) Å for C1], and is almost perpendicular to the fluorobenzene ring (C7–C12), subtending a dihedral angle of 87.30 (5)°. The overall conformation of the molecule is defined by the torsion angles C7—N1—C1—C2 [14.68 (17)°], N1—C1—C2—S1 [106.91 (11)°], C1—C2—S1—C3 [74.53 (10)°] and by the orientation of the ipropyl group, e.g., C1—N1—C4—C6 [139.85 (13)°]. Otherwise, all bond lengths and angles lie within the expected ranges.
of3. Supramolecular features
There are no strong hydrogen bonds in the I (Fig. 2), but there are a number of weaker C—H⋯O and C—H⋯F interactions, which are quantified in Table 1. The most prominent supramolecular constructs are dimers in which inversion-related molecules are linked by C2—H2A⋯O3i and C2i—H2Ai⋯O3 hydrogen bonds [symmetry code: (i) 1 – x, 1 – y, 1 – z]. These dimers also feature close contacts between the sulfone O3 atom and the inversion-related benzene ring to give an O3⋯Cg(C7–C12)i distance of 3.0643 (11) Å (e.g. Gung et al., 2008 and see also Section 4: Database survey). The other weak C—H⋯O interactions involve inversion, translation, and c-glide related molecules (Table 1, Fig. 3a). A Hirshfeld surface analysis using CrystalExplorer (Spackman et al., 2021) shows that almost all atom–atom contacts involve the hydrogen atoms (Fig. 3b–f).
of4. Database survey
A search of the Cambridge Structural Database (CSD, v5.43 with updates through November 2022; Groom et al., 2016) for a molecular fragment consisting of N-phenylacetamide with `any non-H group' attached at the nitrogen atom, the 4-position of the benzene ring, and replacing one hydrogen of the methyl group, yielded 259 hits. A similar fragment, but with `any halogen' at the 4-position on the ring, gave 92 hits. With the halogen restricted to fluorine, twelve hits were returned, and with an isopropyl group attached to the nitrogen atom, only one match was found: CSD refcode QEMHOG (Gao & Ng, 2006): this structure has a 1,3-benzothiazol-2-yl-oxy group attached to the methylene carbon atom of the search fragment.
A search of the CSD for non-bonded close contacts (up to 3.1Å) between S=O oxygen atoms and a benzene-ring centroid (with `any substituent') returned 154 hits, none of which have much else in common with I. A crystallographic and computational study of interactions between oxygen lone pairs and aromatic rings (albeit involving carbon-bound oxygen atoms) was presented by Gung et al. (2008).
There are several other related structures in the CSD, namely: thiamphenicol, D-threo-2,2-dichloro-N-{2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide (CABCIR01; Ghosh et al., 1987), 2,2-dichloro-N-{[1-(fluoromethyl)-2-hydroxy-2-[4- (methylsulfonyl)phenyl]ethyl}acetamide (GAWNIC; Cheng et al., 2005), N-(2,6-dimethylphenyl)-2-(2-{3-[4-(methylsulfonyl)phenyl]-1,2,4-oxadiazol-5-yl}phenoxy)acetamide (AFIFIF; Wang et al., 2007), N-(4-chloro-2-nitrophenyl)-N-(methylsulfonyl)acetamide (WOGWEV; Zia-ur-Rehman et al., 2008), N-(4-methoxy-2-nitro-phenyl)-N-(methylsulfonyl)acetamide (QOTNAP; Zia-ur-Rehman et al., 2009), 2-chloro-N-(4-chloro-2-(2-chlorobenzoyl)phenyl)acetamide (DUPLUW; Dutkiewicz et al., 2010), 2-chloro-N-[2-(2-fluorobenzoyl)-4-nitrophenyl]-N-methylacetamide (EXIVEN; Siddaraju et al., 2011), 2-phenyl-N-(pyrazin-2-yl)acetamide (ROJNAH; Nayak et al., 2014) and 2-(perfluorophenyl)acetamide (LAMRAW; Novikov et al., 2022).
5. Synthesis, crystallization and spectroscopic details
In a 250 ml flask (with a nitrogen inlet and a septum) was placed 5 g of 4-fluoro-N-isopropylbenzenamine dissolved in 50 ml of acetonitrile. After cooling to 273 K, 6.7 g of triethylamine and 4.11 g of 2-(methylthio)acetyl chloride were added. The mixture was stirred at room temperature for 5 h. After this, 100 ml of water were added and the mixture was extracted three times, each with 100 ml of methyl tert-butyl ether (MTBE). The combined organic phases were dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product, N-(4-fluorophenyl)-N-isopropyl-2-(methylthio)acetamide, was used for the next stage with purification (7.5 g).
To a 250 ml round-bottomed flask (with a nitrogen inlet and a septum) was added 7.5 g of N-(4-fluorophenyl)-N-isopropyl-2-(methylthio)acetamide dissolved in 150 ml of dichloromethane. After cooling to 263–273 K, 13.37 g of meta-chloroperbenzoic acid in 100 ml dichloromethane was added slowly at the same temperature. The mixture was stirred at room temperature for 5 h. After this, 200 ml of water were added and the organic layer was separated, and washed with 100 ml of 10% sodium bicarbonate twice. The organic phases were dried over MgSO4 and the solvent was evaporated under reduced pressure. The crude product was purified by over SiO2 (hexane:ethyl acetate 9:1 v/v). The title compound was recrystallized from diethyl ether solution in the form of colorless plates. The overall reaction scheme is shown in Fig. 4.
1H NMR: CDCl3 (400 MHz, δ ppm): 1.097–1.08 [6H, d, (CH3)2]; 3.198 (3H, s, –CH3); 3.664 (2H, s, CH2); 5.006–4.938 (1H, m, –CH); 7.273–7.132 (4H, m, ar H). MS m/z: 273.45 (M)+.
6. Refinement
Crystal data, data collection and structure . Hydrogen atoms were found in difference-Fourier maps, but subsequently included in the using riding models, with constrained C—H distances set to 0.95 Å (Csp2H), 0.98 Å (RCH3), 0.99 Å (R2CH2) and 1.00 Å (R3CH). Uiso(H) parameters were set to values of either 1.2Ueq or 1.5Ueq (RCH3 only) of the attached atom.
details are summarized in Table 2
|
Supporting information
CCDC reference: 2258160
https://doi.org/10.1107/S2056989023003675/hb8062sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023003675/hb8062Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023003675/hb8062Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and CrystalExplorer (Spackman et al., 2021); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).C12H16FNO3S | F(000) = 576 |
Mr = 273.32 | Dx = 1.381 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.9530 (3) Å | Cell parameters from 9889 reflections |
b = 8.7657 (2) Å | θ = 2.8–27.5° |
c = 11.7723 (3) Å | µ = 0.26 mm−1 |
β = 100.457 (1)° | T = 90 K |
V = 1314.45 (5) Å3 | Rounded plate, colourless |
Z = 4 | 0.32 × 0.31 × 0.09 mm |
Bruker D8 Venture dual source diffractometer | 3010 independent reflections |
Radiation source: microsource | 2678 reflections with I > 2σ(I) |
Detector resolution: 7.41 pixels mm-1 | Rint = 0.030 |
φ and ω scans | θmax = 27.5°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −16→16 |
Tmin = 0.833, Tmax = 0.971 | k = −11→11 |
22801 measured reflections | l = −15→15 |
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)] = 0.031 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0327P)2 + 0.7883P] where P = (Fo2 + 2Fc2)/3 |
3010 reflections | (Δ/σ)max = 0.001 |
166 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. |
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 progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.54145 (2) | 0.29322 (3) | 0.38570 (3) | 0.01394 (9) | |
F1 | 0.77308 (7) | 0.83954 (10) | 0.77262 (8) | 0.0265 (2) | |
C1 | 0.70051 (10) | 0.18349 (15) | 0.54790 (11) | 0.0153 (3) | |
N1 | 0.78957 (9) | 0.26470 (13) | 0.58233 (10) | 0.0169 (2) | |
O1 | 0.69978 (7) | 0.04745 (11) | 0.52217 (8) | 0.0193 (2) | |
C2 | 0.59691 (10) | 0.26923 (15) | 0.53498 (11) | 0.0154 (3) | |
H2A | 0.608749 | 0.370378 | 0.572495 | 0.018* | |
H2AB | 0.547429 | 0.211700 | 0.573787 | 0.018* | |
O2 | 0.62454 (7) | 0.33486 (11) | 0.32511 (8) | 0.0208 (2) | |
O3 | 0.45431 (7) | 0.39662 (11) | 0.38023 (8) | 0.0201 (2) | |
C3 | 0.49181 (11) | 0.11358 (15) | 0.33711 (12) | 0.0208 (3) | |
H3A | 0.459299 | 0.120203 | 0.255330 | 0.031* | |
H3B | 0.439182 | 0.081074 | 0.382298 | 0.031* | |
H3C | 0.549247 | 0.039248 | 0.346600 | 0.031* | |
C9 | 0.7902 (1) | 0.68848 (16) | 0.61179 (12) | 0.0191 (3) | |
H9 | 0.794529 | 0.777562 | 0.566931 | 0.023* | |
C8 | 0.79425 (10) | 0.54409 (16) | 0.56408 (12) | 0.0188 (3) | |
H8 | 0.801145 | 0.533426 | 0.485496 | 0.023* | |
C7 | 0.7882 (1) | 0.41507 (15) | 0.63150 (11) | 0.0154 (3) | |
C6 | 0.97208 (12) | 0.2845 (2) | 0.54665 (14) | 0.0295 (3) | |
H6A | 1.036051 | 0.225348 | 0.545252 | 0.044* | |
H6B | 0.988878 | 0.372611 | 0.597886 | 0.044* | |
H6C | 0.943028 | 0.319875 | 0.468411 | 0.044* | |
C5 | 0.93224 (12) | 0.1303 (2) | 0.71320 (14) | 0.0309 (4) | |
H5A | 0.877506 | 0.070798 | 0.740427 | 0.046* | |
H5B | 0.950692 | 0.218725 | 0.763798 | 0.046* | |
H5C | 0.994531 | 0.066468 | 0.714444 | 0.046* | |
C4 | 0.89195 (10) | 0.18467 (16) | 0.59065 (13) | 0.0216 (3) | |
H4 | 0.880049 | 0.092462 | 0.539939 | 0.026* | |
C10 | 0.77975 (10) | 0.69895 (15) | 0.72594 (12) | 0.0180 (3) | |
C11 | 0.77354 (10) | 0.57396 (16) | 0.79470 (11) | 0.0174 (3) | |
H11 | 0.766284 | 0.585728 | 0.873082 | 0.021* | |
C12 | 0.77814 (10) | 0.42986 (15) | 0.74673 (11) | 0.0162 (3) | |
H12 | 0.774416 | 0.341486 | 0.792531 | 0.019* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01361 (16) | 0.01232 (15) | 0.01522 (16) | 0.00096 (11) | 0.00086 (11) | −0.00046 (11) |
F1 | 0.0312 (5) | 0.0167 (4) | 0.0308 (5) | −0.0009 (3) | 0.0033 (4) | −0.0072 (3) |
C1 | 0.0176 (6) | 0.0165 (6) | 0.0114 (6) | 0.0028 (5) | 0.0012 (5) | 0.0006 (5) |
N1 | 0.0158 (5) | 0.0159 (5) | 0.0179 (5) | 0.0033 (4) | 0.0001 (4) | −0.0022 (4) |
O1 | 0.0224 (5) | 0.0142 (5) | 0.0202 (5) | 0.0033 (4) | 0.0015 (4) | −0.0020 (4) |
C2 | 0.0164 (6) | 0.0151 (6) | 0.0142 (6) | 0.0012 (5) | 0.0016 (5) | −0.0018 (5) |
O2 | 0.0210 (5) | 0.0217 (5) | 0.0208 (5) | 0.0013 (4) | 0.0070 (4) | 0.0049 (4) |
O3 | 0.0170 (5) | 0.0180 (5) | 0.0237 (5) | 0.0049 (4) | −0.0007 (4) | −0.0018 (4) |
C3 | 0.0208 (7) | 0.0155 (6) | 0.0243 (7) | −0.0016 (5) | −0.0004 (5) | −0.0058 (5) |
C9 | 0.0184 (6) | 0.0176 (6) | 0.0212 (7) | −0.0010 (5) | 0.0030 (5) | 0.0043 (5) |
C8 | 0.0194 (6) | 0.0220 (7) | 0.0152 (6) | 0.0020 (5) | 0.0038 (5) | 0.0017 (5) |
C7 | 0.0124 (6) | 0.0158 (6) | 0.0171 (6) | 0.0004 (5) | 0.0002 (5) | −0.0017 (5) |
C6 | 0.0227 (7) | 0.0418 (9) | 0.0258 (8) | 0.0094 (7) | 0.0093 (6) | 0.0081 (7) |
C5 | 0.0184 (7) | 0.0345 (9) | 0.0389 (9) | 0.0043 (6) | 0.0030 (6) | 0.0195 (7) |
C4 | 0.0155 (6) | 0.0222 (7) | 0.0258 (7) | 0.0052 (5) | 0.0003 (5) | −0.0036 (6) |
C10 | 0.0147 (6) | 0.0158 (6) | 0.0227 (7) | −0.0007 (5) | 0.0010 (5) | −0.0035 (5) |
C11 | 0.0148 (6) | 0.0225 (7) | 0.0148 (6) | −0.0027 (5) | 0.0021 (5) | −0.0026 (5) |
C12 | 0.0140 (6) | 0.0181 (6) | 0.0160 (6) | −0.0021 (5) | 0.0010 (5) | 0.0025 (5) |
S1—O3 | 1.4399 (9) | C9—H9 | 0.9500 |
S1—O2 | 1.4419 (10) | C8—C7 | 1.3920 (18) |
S1—C3 | 1.7570 (13) | C8—H8 | 0.9500 |
S1—C2 | 1.7862 (13) | C7—C12 | 1.3922 (18) |
F1—C10 | 1.3586 (15) | C6—C4 | 1.519 (2) |
C1—O1 | 1.2300 (16) | C6—H6A | 0.9800 |
C1—N1 | 1.3535 (17) | C6—H6B | 0.9800 |
C1—C2 | 1.5213 (17) | C6—H6C | 0.9800 |
N1—C7 | 1.4411 (16) | C5—C4 | 1.519 (2) |
N1—C4 | 1.4876 (16) | C5—H5A | 0.9800 |
C2—H2A | 0.9900 | C5—H5B | 0.9800 |
C2—H2AB | 0.9900 | C5—H5C | 0.9800 |
C3—H3A | 0.9800 | C4—H4 | 1.0000 |
C3—H3B | 0.9800 | C10—C11 | 1.3732 (19) |
C3—H3C | 0.9800 | C11—C12 | 1.3892 (19) |
C9—C10 | 1.378 (2) | C11—H11 | 0.9500 |
C9—C8 | 1.3896 (19) | C12—H12 | 0.9500 |
O3—S1—O2 | 117.90 (6) | C8—C7—C12 | 120.32 (12) |
O3—S1—C3 | 108.18 (6) | C8—C7—N1 | 120.53 (12) |
O2—S1—C3 | 109.13 (7) | C12—C7—N1 | 119.13 (12) |
O3—S1—C2 | 106.87 (6) | C4—C6—H6A | 109.5 |
O2—S1—C2 | 108.27 (6) | C4—C6—H6B | 109.5 |
C3—S1—C2 | 105.84 (7) | H6A—C6—H6B | 109.5 |
O1—C1—N1 | 123.48 (12) | C4—C6—H6C | 109.5 |
O1—C1—C2 | 119.15 (12) | H6A—C6—H6C | 109.5 |
N1—C1—C2 | 117.29 (11) | H6B—C6—H6C | 109.5 |
C1—N1—C7 | 121.96 (11) | C4—C5—H5A | 109.5 |
C1—N1—C4 | 118.22 (11) | C4—C5—H5B | 109.5 |
C7—N1—C4 | 118.74 (11) | H5A—C5—H5B | 109.5 |
C1—C2—S1 | 110.27 (9) | C4—C5—H5C | 109.5 |
C1—C2—H2A | 109.6 | H5A—C5—H5C | 109.5 |
S1—C2—H2A | 109.6 | H5B—C5—H5C | 109.5 |
C1—C2—H2AB | 109.6 | N1—C4—C6 | 111.23 (12) |
S1—C2—H2AB | 109.6 | N1—C4—C5 | 111.03 (12) |
H2A—C2—H2AB | 108.1 | C6—C4—C5 | 111.49 (12) |
S1—C3—H3A | 109.5 | N1—C4—H4 | 107.6 |
S1—C3—H3B | 109.5 | C6—C4—H4 | 107.6 |
H3A—C3—H3B | 109.5 | C5—C4—H4 | 107.6 |
S1—C3—H3C | 109.5 | F1—C10—C11 | 118.07 (12) |
H3A—C3—H3C | 109.5 | F1—C10—C9 | 118.66 (12) |
H3B—C3—H3C | 109.5 | C11—C10—C9 | 123.26 (12) |
C10—C9—C8 | 118.19 (12) | C10—C11—C12 | 118.32 (12) |
C10—C9—H9 | 120.9 | C10—C11—H11 | 120.8 |
C8—C9—H9 | 120.9 | C12—C11—H11 | 120.8 |
C9—C8—C7 | 119.96 (12) | C11—C12—C7 | 119.94 (12) |
C9—C8—H8 | 120.0 | C11—C12—H12 | 120.0 |
C7—C8—H8 | 120.0 | C7—C12—H12 | 120.0 |
O1—C1—N1—C7 | −168.59 (12) | C1—N1—C7—C12 | 78.93 (16) |
C2—C1—N1—C7 | 14.68 (17) | C4—N1—C7—C12 | −88.93 (15) |
O1—C1—N1—C4 | −0.67 (19) | C1—N1—C4—C6 | 139.85 (13) |
C2—C1—N1—C4 | −177.40 (11) | C7—N1—C4—C6 | −51.84 (16) |
O1—C1—C2—S1 | −69.97 (14) | C1—N1—C4—C5 | −95.38 (15) |
N1—C1—C2—S1 | 106.91 (11) | C7—N1—C4—C5 | 72.93 (16) |
O3—S1—C2—C1 | −170.32 (9) | C8—C9—C10—F1 | −178.38 (11) |
O2—S1—C2—C1 | −42.36 (11) | C8—C9—C10—C11 | 0.2 (2) |
C3—S1—C2—C1 | 74.53 (10) | F1—C10—C11—C12 | 178.69 (11) |
C10—C9—C8—C7 | −0.3 (2) | C9—C10—C11—C12 | 0.1 (2) |
C9—C8—C7—C12 | −0.03 (19) | C10—C11—C12—C7 | −0.36 (19) |
C9—C8—C7—N1 | 178.39 (12) | C8—C7—C12—C11 | 0.34 (19) |
C1—N1—C7—C8 | −99.51 (15) | N1—C7—C12—C11 | −178.10 (11) |
C4—N1—C7—C8 | 92.63 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O3i | 0.99 | 2.31 | 3.2025 (16) | 150 |
C3—H3B···O1ii | 0.98 | 2.55 | 3.5196 (17) | 170 |
C5—H5A···F1iii | 0.98 | 2.50 | 3.4295 (18) | 158 |
C11—H11···O1iv | 0.95 | 2.39 | 3.1851 (16) | 141 |
C12—H12···O2iv | 0.95 | 2.56 | 3.2955 (16) | 134 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y−1, z; (iv) x, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O3i | 0.99 | 2.31 | 3.2025 (16) | 150 |
C3—H3B···O1ii | 0.98 | 2.55 | 3.5196 (17) | 170 |
C5—H5A···F1iii | 0.98 | 2.50 | 3.4295 (18) | 158 |
C11—H11···O1iv | 0.95 | 2.39 | 3.1851 (16) | 141 |
C12—H12···O2iv | 0.95 | 2.56 | 3.2955 (16) | 134 |
O3···Cg(C7–C12)i | 3.0643 (11) |
Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) -x + 1, -y, -z + 1; (iii) x, y - 1, z; (iv) x, -y + 1/2, z + 1/2. |
Acknowledgements
DG is grateful to the DOS in Chemistry, University of Mysore for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.
References
Ahmad, M., Siddiqui, H. L., Gardiner, J. M., Parvez, M. & Aslam, S. (2013). Med. Chem. Res. 22, 794–805. CrossRef CAS Google Scholar
Bruker (2016). APEX3. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, J., Wang, N.-X. & Yang, G.-F. (2005). Acta Cryst. E61, o3628–o3629. CrossRef IUCr Journals Google Scholar
Dutkiewicz, G., Siddaraju, B. P., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o499. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gao, S. & Ng, S. W. (2006). Acta Cryst. E62, o3515–o3516. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ghosh, M., Basak, A. K., Mazumdar, S. K., Párkányi, L. & Kálmán, A. (1987). Acta Cryst. C43, 1552–1555. CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Gung, B. W., Zou, Y., Xu, Z., Amicangelo, J. C., Irwin, D. G., Ma, S. & Zhou, H. C. (2008). J. Org. Chem. 73, 689–693. CrossRef PubMed CAS Google Scholar
Güzel-Akdemir, O., Demir-Yazıcı, K., Trawally, M., Dingiş-Birgül, S. I. & Akdemir, A. (2020). Org. Commun. 13, 33–50. Google Scholar
Hussein, E. M., Al-Rooqi, M. M., Abd El-Galil, S. M. & Ahmed, S. A. (2019). BMC Chem. 13, 91. Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Kreutter, K. D., Lee, L., Lu, T., Mohan, V., Patel, S., Huang, H., Xu, G. & Fitzgerald, M. (2009). US Patent 7.550,474 B2. Google Scholar
Nayak, S. P., Narayana, B., Anthal, S., Gupta, V. K. & Kant, R. (2014). Mol. Cryst. Liq. Cryst. 592, 199–208. CrossRef CAS Google Scholar
Novikov, A. P., Bezdomnikov, A. A., Grigoriev, M. S. & German, K. E. (2022). Acta Cryst. E78, 80–83. CrossRef IUCr Journals Google Scholar
Rouchaud, J., Neus, O., Eelen, H. & Bulcke, R. (2001). Bull. Environ. Contam. Toxicol. 67, 609–616. CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Siddaraju, B. P., Jasinski, J. P., Golen, J. A., Yathirajan, H. S. & Raju, C. R. (2011). Acta Cryst. E67, o2537–o2538. CrossRef IUCr Journals Google Scholar
Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D. & Spackman, M. A. (2021). J. Appl. Cryst. 54, 1006–1011. Web of Science CrossRef CAS IUCr Journals Google Scholar
Verma, V., Yogi, B. & Gupta, S. K. (2020). Res. J. Pharm. Techn. 13, 5158–5164. Google Scholar
Wang, H.-B., Yin, J. & Xing, Z.-T. (2007). Acta Cryst. E63, o3668. CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zia-ur-Rehman, M., Akbar, N., Arshad, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o2092. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zia-ur-Rehman, M., Sepehrianazar, A., Ali, M., Siddiqui, W. A. & Çaylak, N. (2009). Acta Cryst. E65, o941. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zimmerman, L. R., Schneider, R. J. & Thurman, E. M. (2002). J. Agric. Food Chem. 50, 1045–1052. CrossRef PubMed CAS 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.