In the title molecule, C11H11BrO3, the dihydroindene moiety is essentially planar but with a slight twist in the saturated portion of the five-membered ring. The methoxy groups lie close to the above plane. In the crystal, π-stacking interactions between six-membered rings form stacks of molecules extending along the a-axis directions, which are linked by weak C—H⋯O and C—H⋯Br hydrogen bonds.
Keywords: crystal structure, dihydroindenone, hydrogen bond, π-stacking
Abstract
In the title molecule, C11H11BrO3, the dihydroindene moiety is essentially planar but with a slight twist in the saturated portion of the five-membered ring. The methoxy groups lie close to the above plane. In the crystal, π-stacking interactions between six-membered rings form stacks of molecules extending along the a-axis direction, which are linked by weak C—H⋯O and C—H⋯Br hydrogen bonds. A Hirshfeld surface analysis was performed showing H⋯H, O⋯H/H⋯O and Br⋯H/H⋯Br contacts make the largest contributions to intermolecular interactions in the crystal.
1. Chemical context
Aberrant expression of protein kinases is a hallmark of several cancers, and small molecules targeting specific kinases are in clinical use as cancer therapeutics (Du & Lovly, 2018 ▸; Kannaiyan & Mahadevan, 2018 ▸; Roskoski, 2023 ▸). Development of resistance to the kinase inhibitors is a frequent occurrence, which motivates a continuing search for new kinase inhibitors (Yang et al., 2022 ▸). One of the key characteristics of the kinase inhibitors is the capacity to form two hydrogen bonds, one as donor and one as acceptor, with the hinge region of the kinase (Arter et al., 2022 ▸; Attwood et al., 2021 ▸). Planarity with two functional groups capable of making the two essential hydrogen bonds, along with other substituents to target the unique residues of the ATP binding pocket for potency and specificity, are the fundamental structural features of kinase inhibitors.
We have developed 5-hydroxy-1,4-naphthoquinones as HER2 and PIM1 kinase inhibitors (Schroeder et al., 2014 ▸, 2016 ▸; Sridhar et al., 2014 ▸). To circumvent the issue of oxidation-reduction reactions of the quinone moiety, 5,7-dihydroxy-2,3-dihydro-1H-inden-1-one is currently under development as a new core structure. The new series based upon this platform is capable of making the requisite hydrogen bonds to the kinase hinge region and has potential for functionalization at the 2, 3, 4, 5 and 6 positions to enable specific and potent inhibition of the kinase of interest. Bromination serves as an initial step for functionalizing the core structure of 5,7-dimethoxy-2,3-dihydro-1H-inden-1-one.
Bromination by free radical or electrophilic aromatic substitution mechanisms using N-bromosuccinimide (NBS) is known to introduce a bromine atom on an allylic or benzylic carbon atom or on an aromatic ring (Djerassi, 1948 ▸; Li et al., 2014 ▸). When subjected to bromination with NBS in benzene in the presence of azobisisobutyronitrile (AIBN) for 15 h at ambient temperature, 5,7-dimethoxy-2,3-dihydro-1H-inden-1-one yielded a single product. From among the product outcomes depicted as 1A, 1B and 1C in Fig. 1 ▸, NMR spectroscopy indicated that electrophilic aromatic substitution had occurred to form a single species – either 1A or 1B. X-ray crystallography has identified the product as 1B (Fig. 2 ▸), the detailed structural characterization and crystal packing arrangement of which we describe herein.
Figure 1.
Synthesis scheme for 4-bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one.
Figure 2.
The title molecule with labeling scheme and 50% probability displacement ellipsoids.
2. Structural commentary
The dihydroindene moiety is planar to within 0.045 (3) Å (r.m.s. deviation of the contributing atoms = 0.003 Å) with C9 that distance from one side of the mean plane and C8 0.018 (4) Å from the opposite side. This twist in the five-membered ring is towards the upper end of the range seen in related structures (see Database survey). Both methoxy groups are nearly coplanar with the C1–C6 ring as indicated by the C10—O1—C3—C4 and C11—O2—C5—C4 torsion angles which are, respectively, 2.7 (4) and 6.6 (5)°. All bond distances and interbond angles are as expected for the formulation given.
3. Supramolecular features
In the crystal (Fig. 3 ▸), the molecules stack along the a-axis direction with significant π interactions between the C1–C6 rings [centroid–centroid distance = 3.5606 (16) Å, dihedral angle = 1.61 (13)°, slippage alternates between 0.93 and 0.96 Å]. The stacks are linked by weak C11—H11C⋯O3 and C11—H11C⋯Br1 hydrogen bonds (Table 1 ▸ and Figs. 4 ▸ and 5 ▸).
Figure 3.
A portion of one stack viewed along the c-axis direction with the π-stacking interactions depicted by dashed lines. Non-interacting hydrogen atoms are omitted for clarity.
Table 1. Hydrogen-bond geometry (Å, °).
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| C11—H11A⋯Br1i | 0.98 | 3.06 | 3.605 (4) | 116 |
| C11—H11C⋯Br1ii | 0.98 | 2.90 | 3.683 (3) | 137 |
| C11—H11C⋯O3iii | 0.98 | 2.58 | 3.288 (4) | 129 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 4.
Packing viewed along the c-axis direction with the C—H⋯O and C—H⋯Br hydrogen bonds depicted, respectively, by black and green dashed lines. The π-stacking interactions are depicted by orange dashed lines and non-interacting hydrogen atoms are omitted for clarity.
Figure 5.
Packing viewed along the a-axis direction with the C—H⋯O and C—H⋯Br hydrogen bonds depicted, respectively, by black and green dashed lines. The π-stacking interactions are depicted by orange dashed lines and non-interacting hydrogen atoms are omitted for clarity.
4. Database survey
A search of the Cambridge Structural Database (CSD; updated to May 2024; Groom et al., 2016 ▸) with the search fragment shown in Fig. 6 ▸ returned 58 hits of which 25 are most similar to the title molecule with the remainder having additional rings fused to the aromatic ring or being metal complexes. Interestingly, there are no examples with three substituents on the six-membered ring, but the search found 18 structures with one substituent, six with two and the unsubstituted parent molecule (R = R′ = R′′ = H, QQQGMJ; Morin et al., 1974 ▸, QQQGMJ01; Peña Ruiz et al., 2004 ▸). There are two structures with R′′ = Br, namely AWOBOF (R = R′ = H; Aldeborgh et al., 2014 ▸) and LAQCAJ (R = H, R′ = NH2; Çelik et al., 2012 ▸), and one with R = R′ = OMe, R" = H (MXINDO10; Gupta et al., 1984 ▸). The other structures with two substituents have R = OMe, R′ = H, R′′ = 4-fluorobenzoyl (CAPHEJ; Chang & Lee, 2011 ▸), R = OH, R′ = H, R′′ = 4-methoxybenzoyl (CAPHIN; Chang & Lee, 2011 ▸), R = H, R′ = H, R′′ = OPri (CETCAG; Coyanis et al., 2006 ▸) and R′ = H, R = R′′ = Me (MUQCEG; Johnson et al., 2002 ▸). In AWOBOF and LAQCAJ, the C—Br distances are virtually the same as in the title molecule [1.892 (3) Å] and the twist in the five-membered ring is slightly less. Among the other disubstituted molecules, the greatest deviation of the saturated carbon atoms of the five-membered ring from the mean plane of the bicyclic moiety is in CAPHIN [0.091 (2) and −0.122 (2) Å] while the least is in MUQCEG [0.016 (3) and −0.012 (3) Å]. As in the title molecule, the methyl carbon atoms of the methoxy groups in CAPHEJ, CETCAG and MXINDO10 lie in or very close to the mean plane of the nine-membered ring system. Where π-stacking of the six-membered aromatic rings occurs in the disubstituted examples, this involves only pairs of molecules (LAQCAJ and MXINDO10) rather than extended stacks.
Figure 6.
The fragment used in the database survey.
5. Hirshfeld surface analysis
The Hirshfeld surface was constructed with CrystalExplorer 21.5 (Spackman et al., 2021 ▸) with descriptions of the several plots obtained and their interpretations described elsewhere (Tan et al., 2019 ▸). Fig. 7 ▸a shows the surface plotted over dnorm in the range −0.1265 to 1.2968 in arbitrary units with four neighboring molecules. The two above and below the surface constitute part of the column formed by the π-stacking interactions, while the two at the right are part of an adjacent column showing the C—H⋯O and C—H⋯Br hydrogen bonds that link columns. Fig. 7 ▸b shows the surface plotted over the shape function and the flat area in the center containing red and blue triangles clearly shows the π-stacking interactions. The 2-D fingerprint plots are shown in Fig. 8 ▸, from which it was determined that H⋯H contacts contribute 37.1% of the total (Fig. 8 ▸b) while O⋯H/H⋯O (Fig. 8 ▸c) and Br⋯H/H⋯Br (Fig. 8 ▸d) contacts contribute, respectively, 26.3% and 16.8%. The C⋯C contacts, which are primarily the π-stacking interactions, contribute 9.8%. Other contacts make minimal contributions.
Figure 7.
The Hirshfeld surface plotted over (a) dnorm and (b) over the shape index including two additional molecules in the stack plus two more in an adjacent stack with the C—H⋯O and C—H⋯Br hydrogen bonds shown by green dashed lines.
Figure 8.
Fingerprint plots showing (a) all contacts, (b) H⋯H contacts, (c) O⋯H/H⋯O contacts, (d) Br⋯H/H⋯Br contacts, and (e) C⋯C contacts.
6. Synthesis and crystallization
To a solution of 5,7-dimethoxy-2,3-dihydro-1H-inden-1-one (1.0 g, 5.2 mmol) in benzene (15 mL) were added N-bromosuccinimide (0.93 g, 5.2 mmol) and a catalytic amount of azobisisobutyronitrile at room temperature. This reaction mixture was stirred for 15 h, with progress being monitored by TLC. Upon completion of the reaction, the benzene was removed by distillation, and water was added. The resulting slurry was stirred for 30 min, and the crude 4-bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one was then collected by vacuum filtration and dried on the filter by continued application of the vacuum for an additional 30 min. Yield: 1.27 g of off-white solid, 4.7 mmol, 90%, m.p. 498–500 K. Rf: 0.4 (1:1 ethyl acetate:hexane). 1H NMR (δ, ppm in DMSO-d6): 6.64 (s, 1 H), 3.97 (s, 3 H), 3.88 (s, 3 H), 2.87–2.84 (m, 2 H), 2.55–2.52 (m, 2 H). 13C NMR (δ, ppm in DMSO-d6): 201.62, 162.29, 158.85, 157.96, 120.11, 99.75, 96.44, 57.66, 56.55, 37.01, 27.31. HRMS [M + H]+: 79Br calculated, 270.9970; found, 270.9974; 81Br calculated, 272.9949; found, 272.9946. The NMR spectra (see supporting information) were acquired using a Bruker 400 MHz spectrometer, while the mass spectrum was obtained using a Thermo LTQ-Orbitrap LC/MS/MS System/UltiMate 3000 HPLC. The compound was crystallized from 15% ethyl acetate in hexane.
7. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Hydrogen atoms were included as riding contributions in idealized positions with isotropic displacement parameters tied to those of the attached atoms. One reflection affected by the beamstop was omitted from the final refinement.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C11H11BrO3 |
| M r | 271.11 |
| Crystal system, space group | Orthorhombic, Pna21 |
| Temperature (K) | 150 |
| a, b, c (Å) | 7.0928 (5), 14.3933 (10), 10.0419 (7) |
| V (Å3) | 1025.17 (12) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 3.99 |
| Crystal size (mm) | 0.22 × 0.06 × 0.03 |
| Data collection | |
| Diffractometer | Bruker D8 QUEST PHOTON 3 diffractometer |
| Absorption correction | Numerical (SADABS; Krause et al., 2015 ▸) |
| Tmin, Tmax | 0.70, 0.89 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 13923, 2534, 2366 |
| R int | 0.030 |
| (sin θ/λ)max (Å−1) | 0.667 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.056, 1.08 |
| No. of reflections | 2534 |
| No. of parameters | 139 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.41, −0.39 |
| Absolute structure | Flack x determined using 1025 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013 ▸). Refined as an inversion twin |
| Absolute structure parameter | 0.039 (12) |
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989024006522/jy2050sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989024006522/jy2050Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989024006522/jy2050Isup4.cml
NMR and mass spectra. DOI: 10.1107/S2056989024006522/jy2050sup3.pdf
CCDC reference: 2367432
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
Tulane University is acknowledged for its ongoing support with operational costs for the diffraction facility.
supplementary crystallographic information
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Crystal data
| C11H11BrO3 | Dx = 1.757 Mg m−3 |
| Mr = 271.11 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, Pna21 | Cell parameters from 9927 reflections |
| a = 7.0928 (5) Å | θ = 2.8–28.2° |
| b = 14.3933 (10) Å | µ = 3.99 mm−1 |
| c = 10.0419 (7) Å | T = 150 K |
| V = 1025.17 (12) Å3 | Block, colourless |
| Z = 4 | 0.22 × 0.06 × 0.03 mm |
| F(000) = 544 |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Data collection
| Bruker D8 QUEST PHOTON 3 diffractometer | 2534 independent reflections |
| Radiation source: fine-focus sealed tube | 2366 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.030 |
| Detector resolution: 7.3910 pixels mm-1 | θmax = 28.3°, θmin = 2.8° |
| φ and ω scans | h = −9→8 |
| Absorption correction: numerical (SADABS; Krause et al., 2015) | k = −19→19 |
| Tmin = 0.70, Tmax = 0.89 | l = −13→13 |
| 13923 measured reflections |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Refinement
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
| wR(F2) = 0.056 | w = 1/[σ2(Fo2) + (0.0247P)2 + 0.097P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.001 |
| 2534 reflections | Δρmax = 0.41 e Å−3 |
| 139 parameters | Δρmin = −0.39 e Å−3 |
| 1 restraint | Absolute structure: Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). Refined as an inversion twin |
| Primary atom site location: dual | Absolute structure parameter: 0.039 (12) |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Special details
| Experimental. The diffraction data were obtained from 3 sets of frames, each of width 0.50 ° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was 10.00 sec/frame. |
| 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. One reflection affected by the beamstop was omitted from the final refinement. Refined as a 2-component inversion twin. |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| Br1 | 0.26616 (4) | 0.95085 (2) | 0.61925 (8) | 0.02538 (11) | |
| O1 | 0.2173 (3) | 0.77072 (17) | 0.7610 (2) | 0.0259 (5) | |
| O2 | 0.3585 (3) | 0.56410 (13) | 0.3929 (2) | 0.0217 (5) | |
| O3 | 0.4552 (3) | 0.66801 (14) | 0.1506 (2) | 0.0265 (6) | |
| C1 | 0.3410 (4) | 0.81569 (19) | 0.4184 (3) | 0.0153 (6) | |
| C2 | 0.2942 (4) | 0.8293 (2) | 0.5505 (3) | 0.0171 (6) | |
| C3 | 0.2657 (3) | 0.7523 (2) | 0.6327 (5) | 0.0184 (7) | |
| C4 | 0.2862 (4) | 0.6621 (2) | 0.5822 (3) | 0.0191 (7) | |
| H4 | 0.266176 | 0.610159 | 0.638782 | 0.023* | |
| C5 | 0.3355 (4) | 0.6484 (2) | 0.4500 (3) | 0.0173 (6) | |
| C6 | 0.3652 (4) | 0.7259 (2) | 0.3673 (3) | 0.0155 (6) | |
| C7 | 0.4207 (4) | 0.73116 (19) | 0.2271 (3) | 0.0172 (6) | |
| C8 | 0.4287 (5) | 0.8336 (2) | 0.1892 (3) | 0.0214 (7) | |
| H8A | 0.341666 | 0.846478 | 0.114395 | 0.026* | |
| H8B | 0.558028 | 0.850884 | 0.161645 | 0.026* | |
| C9 | 0.3700 (4) | 0.8891 (2) | 0.3127 (3) | 0.0201 (7) | |
| H9A | 0.470112 | 0.933291 | 0.339159 | 0.024* | |
| H9B | 0.252057 | 0.923961 | 0.296052 | 0.024* | |
| C10 | 0.1933 (6) | 0.6945 (3) | 0.8509 (4) | 0.0339 (9) | |
| H10A | 0.153765 | 0.717936 | 0.938144 | 0.051* | |
| H10B | 0.312996 | 0.661020 | 0.860085 | 0.051* | |
| H10C | 0.096895 | 0.652214 | 0.816037 | 0.051* | |
| C11 | 0.3100 (5) | 0.4840 (2) | 0.4710 (4) | 0.0248 (7) | |
| H11A | 0.320697 | 0.428012 | 0.415954 | 0.037* | |
| H11B | 0.180267 | 0.490130 | 0.503313 | 0.037* | |
| H11C | 0.396091 | 0.479171 | 0.547044 | 0.037* |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.03113 (18) | 0.02045 (15) | 0.02457 (17) | −0.00137 (11) | 0.0002 (2) | −0.00798 (19) |
| O1 | 0.0341 (14) | 0.0296 (14) | 0.0140 (12) | −0.0017 (10) | 0.0020 (10) | −0.0017 (10) |
| O2 | 0.0326 (13) | 0.0131 (10) | 0.0193 (11) | −0.0007 (9) | 0.0028 (10) | 0.0019 (9) |
| O3 | 0.0366 (13) | 0.0231 (11) | 0.0200 (14) | 0.0059 (9) | 0.0048 (9) | −0.0025 (9) |
| C1 | 0.0122 (14) | 0.0157 (13) | 0.0182 (15) | −0.0012 (12) | −0.0021 (11) | 0.0019 (11) |
| C2 | 0.0160 (15) | 0.0153 (14) | 0.0201 (16) | 0.0006 (12) | −0.0021 (12) | −0.0023 (12) |
| C3 | 0.0131 (12) | 0.0277 (14) | 0.014 (2) | −0.0014 (10) | −0.0025 (13) | 0.0032 (17) |
| C4 | 0.0184 (15) | 0.0200 (15) | 0.0188 (17) | −0.0014 (12) | −0.0007 (11) | 0.0039 (11) |
| C5 | 0.0145 (15) | 0.0163 (14) | 0.0212 (15) | 0.0008 (12) | −0.0018 (12) | 0.0017 (12) |
| C6 | 0.0128 (14) | 0.0173 (14) | 0.0163 (15) | −0.0007 (11) | 0.0003 (11) | 0.0010 (12) |
| C7 | 0.0160 (15) | 0.0171 (14) | 0.0186 (15) | 0.0021 (11) | −0.0013 (12) | 0.0024 (12) |
| C8 | 0.0281 (18) | 0.0188 (15) | 0.0174 (16) | 0.0020 (13) | 0.0053 (13) | 0.0046 (12) |
| C9 | 0.0239 (17) | 0.0156 (15) | 0.0210 (15) | −0.0010 (12) | 0.0022 (13) | 0.0001 (12) |
| C10 | 0.045 (2) | 0.039 (2) | 0.0182 (19) | −0.0062 (17) | 0.0017 (15) | 0.0042 (16) |
| C11 | 0.0346 (19) | 0.0144 (14) | 0.0254 (18) | −0.0033 (14) | −0.0029 (15) | 0.0046 (14) |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Geometric parameters (Å, º)
| Br1—C2 | 1.892 (3) | C6—C7 | 1.465 (4) |
| O1—C3 | 1.359 (6) | C7—C8 | 1.524 (4) |
| O1—C10 | 1.431 (4) | C8—C9 | 1.532 (4) |
| O2—C5 | 1.352 (3) | C8—H8A | 0.9900 |
| O2—C11 | 1.437 (4) | C8—H8B | 0.9900 |
| O3—C7 | 1.215 (3) | C9—H9A | 0.9900 |
| C1—C2 | 1.381 (4) | C9—H9B | 0.9900 |
| C1—C6 | 1.401 (4) | C10—H10A | 0.9800 |
| C1—C9 | 1.512 (4) | C10—H10B | 0.9800 |
| C2—C3 | 1.396 (5) | C10—H10C | 0.9800 |
| C3—C4 | 1.401 (5) | C11—H11A | 0.9800 |
| C4—C5 | 1.387 (4) | C11—H11B | 0.9800 |
| C4—H4 | 0.9500 | C11—H11C | 0.9800 |
| C5—C6 | 1.406 (4) | ||
| C3—O1—C10 | 118.6 (3) | C7—C8—H8A | 110.3 |
| C5—O2—C11 | 117.4 (3) | C9—C8—H8A | 110.3 |
| C2—C1—C6 | 120.8 (3) | C7—C8—H8B | 110.3 |
| C2—C1—C9 | 127.5 (3) | C9—C8—H8B | 110.3 |
| C6—C1—C9 | 111.8 (3) | H8A—C8—H8B | 108.6 |
| C1—C2—C3 | 119.4 (3) | C1—C9—C8 | 104.0 (2) |
| C1—C2—Br1 | 120.4 (2) | C1—C9—H9A | 111.0 |
| C3—C2—Br1 | 120.2 (3) | C8—C9—H9A | 111.0 |
| O1—C3—C2 | 116.2 (3) | C1—C9—H9B | 111.0 |
| O1—C3—C4 | 123.4 (3) | C8—C9—H9B | 111.0 |
| C2—C3—C4 | 120.4 (4) | H9A—C9—H9B | 109.0 |
| C5—C4—C3 | 120.3 (3) | O1—C10—H10A | 109.5 |
| C5—C4—H4 | 119.8 | O1—C10—H10B | 109.5 |
| C3—C4—H4 | 119.8 | H10A—C10—H10B | 109.5 |
| O2—C5—C4 | 124.4 (3) | O1—C10—H10C | 109.5 |
| O2—C5—C6 | 116.3 (3) | H10A—C10—H10C | 109.5 |
| C4—C5—C6 | 119.3 (3) | H10B—C10—H10C | 109.5 |
| C1—C6—C5 | 119.8 (3) | O2—C11—H11A | 109.5 |
| C1—C6—C7 | 109.7 (2) | O2—C11—H11B | 109.5 |
| C5—C6—C7 | 130.5 (3) | H11A—C11—H11B | 109.5 |
| O3—C7—C6 | 128.6 (3) | O2—C11—H11C | 109.5 |
| O3—C7—C8 | 124.0 (3) | H11A—C11—H11C | 109.5 |
| C6—C7—C8 | 107.5 (2) | H11B—C11—H11C | 109.5 |
| C7—C8—C9 | 107.0 (2) | ||
| C6—C1—C2—C3 | −1.8 (4) | C9—C1—C6—C5 | −177.2 (3) |
| C9—C1—C2—C3 | 177.4 (3) | C2—C1—C6—C7 | −177.9 (3) |
| C6—C1—C2—Br1 | 178.9 (2) | C9—C1—C6—C7 | 2.8 (3) |
| C9—C1—C2—Br1 | −1.9 (4) | O2—C5—C6—C1 | 178.9 (3) |
| C10—O1—C3—C2 | −177.7 (3) | C4—C5—C6—C1 | −1.3 (4) |
| C10—O1—C3—C4 | 2.7 (4) | O2—C5—C6—C7 | −1.0 (5) |
| C1—C2—C3—O1 | −179.1 (3) | C4—C5—C6—C7 | 178.8 (3) |
| Br1—C2—C3—O1 | 0.3 (3) | C1—C6—C7—O3 | 179.4 (3) |
| C1—C2—C3—C4 | 0.6 (4) | C5—C6—C7—O3 | −0.7 (5) |
| Br1—C2—C3—C4 | 179.9 (2) | C1—C6—C7—C8 | −0.7 (3) |
| O1—C3—C4—C5 | 179.8 (3) | C5—C6—C7—C8 | 179.2 (3) |
| C2—C3—C4—C5 | 0.2 (4) | O3—C7—C8—C9 | 178.4 (3) |
| C11—O2—C5—C4 | 6.6 (5) | C6—C7—C8—C9 | −1.5 (3) |
| C11—O2—C5—C6 | −173.7 (3) | C2—C1—C9—C8 | 177.2 (3) |
| C3—C4—C5—O2 | 179.9 (3) | C6—C1—C9—C8 | −3.6 (3) |
| C3—C4—C5—C6 | 0.2 (4) | C7—C8—C9—C1 | 3.0 (3) |
| C2—C1—C6—C5 | 2.1 (4) |
4-Bromo-5,7-dimethoxy-2,3-dihydro-1H-inden-1-one . Hydrogen-bond geometry (Å, º)
| D—H···A | D—H | H···A | D···A | D—H···A |
| C11—H11A···Br1i | 0.98 | 3.06 | 3.605 (4) | 116 |
| C11—H11C···Br1ii | 0.98 | 2.90 | 3.683 (3) | 137 |
| C11—H11C···O3iii | 0.98 | 2.58 | 3.288 (4) | 129 |
Symmetry codes: (i) −x+1/2, y−1/2, z−1/2; (ii) x+1/2, −y+3/2, z; (iii) −x+1, −y+1, z+1/2.
Funding Statement
This work was funded by National Institutes of Health grant 8G12MD007595-04; National Institutes of Health grant 3U54MD007595-15S1; National Science Foundation grant 2300447; Louisiana Board of Regents grant LEQSF-(2002-03)-ENH-TR-67.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989024006522/jy2050sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989024006522/jy2050Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989024006522/jy2050Isup4.cml
NMR and mass spectra. DOI: 10.1107/S2056989024006522/jy2050sup3.pdf
CCDC reference: 2367432
Additional supporting information: crystallographic information; 3D view; checkCIF report