Both title compounds are analogs of 1-indanone that are substituted at

Both title compounds are analogs of 1-indanone that are substituted at the 6-position with chlorine and bromine. & Steiner 1999 ?) as well as specifically in the case of 1-indanone itself (Ruiz van der Waals contacts specifically C-H?O inter-actions without any π-stacking. The C-H?O inter-actions (Fig.?3 ? and Table?1 ?) connect the indanone oxygen atom with methyl-ene hydrogen atoms AMG 208 on neighboring mol-ecules into a two-mol-ecule-thick AMG 208 sheet parallel to the (100) plane (Fig.?4 ?). These sheets further pack together without any notable inter-molecular contacts. Mouse monoclonal to CD8/CD45RA (FITC/PE). The closest Cl?Cl contact between the sheets 3.728 is somewhat longer than the sum of the van der Waals radii of chlorine 3.5 (Bondi 1964 ?). Figure 3 A view of the inter-molecular C-H?O contacts in 6-chloro-indan-1-one (I). See Table?1 ? for symmetry codes (i) and (ii). In this and subsequent figures the C-H?inter-actions are … Figure 4 A view of the sheet structure in 6-chloro-indan-1-one (I) formed by C-H?O contacts. See Table?1 ? for symmetry codes (i) and (ii). Table 1 Hydrogen-bond geometry (? °) for (I) The mol-ecular packing in the bromo analog 6 (II) is distinct from that found in (I). The notable inter-molecular inter-actions observed include π-stacking Br?O C-H?O and C-H?Br inter-actions. The offset face-to-face π-stacking can be seen to extend along the crystallographic axis (Fig.?5 ?) with the mol-ecules stacking in an alternating head-to-tail fashion featuring a C-H?Br inter-action with an H?Br distance of 3.05?? (Fig.?5 ? and Table?2 ?). The π-stacking is characterized by a centroid-to-centroid distance of 3.850?(3)?? centroid-to-plane distances of 3.530?(2) and 3.603?(2)?? and ring offsets of 1 1.358?(3) and 1.536?(3)?? that result in a plane-to-plane angle of 3.1?(1)°. The π-stacked chains of (II) are linked into a three-dimensional lattice by C-H?O inter-actions and a Br?O contact (Fig.?6 ? and Table?2 ?). The Br?O contact at a distance of 3.018?(2)?? is slightly shorter than the sum of the van der Waals radii 3.37 (Bondi 1964 ?). This inter-action is even shorter than the Br?O contact in the isomeric 4-bromo-indan-1-one [3.129?(1)??; Aldeborgh = 5.9?Hz C= 5.9?Hz C= 8.2?Hz Car-yl = 1.6?Hz = 8.1?Hz Car-yl = 5.8?Hz C= 5.9?Hz C= 8.1?Hz Car-yl = 1.9?Hz = 8.1?Hz Car-yl (Sheldrick 2008 ?) 6 AMG 208 (II) was refined as a two-component non-merohedral twin BASF 0.0762?(5). Carbon-bound hydrogen atoms were included in calculated positions and refined using a riding model at C-H = 0.95 and 0.99?? and = 211.06= 6.489 (2) ?Cell parameters from 9955 reflections= 17.101 (6) ?θ = 2.4-30.6°= 7.224 (3) ?μ = 5.19 mm?1β = 102.964 (5)°= 125 K= 781.2 (5) ?3Block colourless= 40.40 × 0.21 × 0.05 mm View it in a separate window AMG 208 Data collection Bruker APEXII CCD diffractometer4453 independent reflectionsRadiation source: fine-focus sealed tube3600 reflections with > 2σ(= ?9→9Absorption correction: multi-scan (= 0→24= 0→104453 measured reflections View it in a separate window Refinement Refinement on = 1/[σ2(= (= 1.03(Δ/σ)max = 0.0014453 reflectionsΔρmax = 1.15 e ??3101 parametersΔρmin = ?1.15 e ??3 View it in a separate window Special details Experimental. BASF 0.0762?(5)Geometry. All esds AMG 208 (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 AMG 208 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. Refined as a 2-component twin View it in a separate window Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (?2) xyzUiso*/UeqBr10.34409 (5)0.45945 (2)0.19485 (4)0.02009 (16)O10.4929 (3)0.12531 (11)0.2717 (4)0.0233 (5)C10.3083 (4)0.14135 (17)0.2062 (4)0.0159 (5)C20.1260 (4)0.08352 (17)0.1453 (4)0.0179 (5)H2A0.11170.05020.25370.021*H2B0.15150.04940.04190.021*C3?0.0764 (5)0.13304 (17)0.0755 (4)0.0192.