research communications
Different packing motifs mediated by weak interactions and
in the crystal structures of five 2-(benzylidene)benzosuberone derivativesaDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, bFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos Manguinhos, 21041-250 Rio de Janeiro, RJ, Brazil, and cCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
*Correspondence e-mail: w.harrison@abdn.ac.uk
The syntheses and crystal structures of five 2-benzylidene-1-benzosuberone [1-benzosuberone is 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one] derivatives, viz. 2-(4-methoxybenzylidene)-1-benzosuberone, C19H18O2, (I), 2-(4-ethoxybenzylidene)-1-benzosuberone, C20H20O2, (II), 2-(4-benzylbenzylidene)-1-benzosuberone, C25H22O2, (III), 2-(4-chlorobenzylidene)-1-benzosuberone, C18H15ClO, (IV) and 2-(4-cyanobenzylidene)-1-benzosuberone, C19H15NO, (V), are described. The conformations of the benzosuberone fused six- plus seven-membered ring fragments are very similar in each case, but the dihedral angles between the fused benzene ring and the pendant benzene ring differ somewhat, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). Key features of the packing include pairwise C—H⋯O hydrogen bonds for (II) and (IV), and pairwise C—H⋯N hydrogen bonds for (V), which generate inversion dimers in each case. The packing for (I) and (III) feature C—H⋯O hydrogen bonds, which lead to [010] and [100] chains, respectively. Weak C—H⋯π interactions consolidate the structures and weak aromatic π–π stacking is seen in (II) [centroid–centroid separation = 3.8414 (7) Å] and (III) [3.9475 (7) Å]. A polymorph of (I) crystallized from a different solvent has been reported previously [Dimmock et al. (1999) J. Med. Chem. 42, 1358–1366] in the same but with a packing motif based on inversion dimers resembling that seen in (IV) in the present study. The Hirshfeld surfaces and fingerprint plots for (I) and its polymorph are compared and structural features of the 2-benzylidene-1-benzosuberone family of phases are surveyed.
Keywords: crystal structure; suberone; polymorphism.
1. Chemical context
The structurally related 2-benzylidenebenzocycloalkanone compounds, viz. (E)-2-benzylidene-2,3-dihydro-1H-inden-1-one (n = 1), (E)-2-benzylidene-1-tetralone (n = 2) and (E)-2-benzylidene-1-benzosuberone (n = 3), which differ with respect to the number of methylene groups, n, in the alkanone ring fused to the benzene ring (see Scheme 1) have attracted attention in a number of areas. Their biological activities include antitumour (e.g. Gautam et al., 2016: Dimmock et al., 1999, 2002), antimycotic (Al-Nakib et al., 1997) and antifungal (Gupta & Jain, 2015) properties. Their physical properties include nonlinear optical (Watson et al., 1993) and UV hypsochromic shifts and fluorescence effects (Fodor et al., 2011). It may be noted that these compounds can be considered as fused-ring analogues of (i.e. the `n = 0' family), which might allow for `tuneable' conformational control of the molecule by changing the number of methylene groups in the cycloalkanone ring (Dimmock et al., 1999).
In continuation of our earlier reports of the crystal structures and Hirshfeld surface analyses of a number of (E)-2-benzylidene-2,3-dihydro-1H-inden-1-one derivatives (Baddeley et al., 2017a) and (E)-2-benzylidene-1-tetralone (Baddeley et al., 2017b), we now describe the syntheses and crystal structures of 2-(4-methoxybenzylidene)-1-benzosuberone, (I), 2-(4-ethoxybenzylidene)-1-benzosuberone, (II), 2-(4-benzylbenzylidene)-1-benzosuberone, (III), 2-(4-chlorobenzylidene)-1-benzosuberone, (IV), and 2-(4-cyanobenzylidene)-1-benzosuberone, (V) (see Scheme 2).
2. Structural commentary
The molecular structures of (I)–(V) are shown in Figs. 1–5, respectively. Each molecule is the expected product arising from the base-catalysed condensation reaction between 1-benzosuberone and the appropriate 4-substituted benzaldehyde derivative (see Experimental section). The conformations of the benzosuberone fragments in (I)–(V) are almost identical, as shown by the overlay plot generated with QMOL (Gans & Shalloway, 2001) shown in Fig. 6. The seven-membered ring, which is conformationally constrained by being fused to the C6–C11 benzene ring and by the presence of the sp2-hybridized atoms C1 and C2, at least approximates to a boat conformation; in the case of (I), atoms C3/C4/C6/C11 are roughly coplanar (r.m.s. deviation = 0.095 Å), with C5 as the prow [deviation = 0.6139 (15) Å] and C1 and C2 as the stern [deviations = 1.0114 (16) and 1.0154 (16) Å, respectively]. This conformation results in a substantial degree of twist about the C11—C1 bond [C10—C11—C1=O1 = 36.06 (14)°] and O1 deviates from the C6–C11 benzene-ring plane by 0.7212 (17) Å. The corresponding data for the seven-membered rings in (II)–(V) are very similar to those for (I) and are not stated here.
The dihedral angles between the C6–C11 fused benzene ring and the C13–C18 pendant benzene ring are clustered in a ∼12° range, with values of 23.79 (3) for (I), 24.60 (4) for (II), 33.72 (4) for (III), 29.93 (8) for (IV) and 21.81 (7)° for (V). A comparison of the C1—C2—C12—C13 and C2—C12—C13—C14 torsion angles for (I) [−179.67 (10) and −33.81 (17)°, respectively] indicates that the twisting largely occurs about the C12—C13 bond, and the same conclusion can be drawn for (II)–(V).
For (I), the C19 atom of the methoxy group is close to coplanar with its attached benzene ring [deviation = 0.1079 (19) Å] and for (II) the ethoxy group has an extended conformation [C16—O2—C19—C20 = 178.58 (10)°]. For (III), an additional dihedral angle between the C13–C18 benzene ring and the terminal C20–C25 benzene ring of 78.78 (3)° is observed. Otherwise, the geometrical data for (I)–(V) are unexceptional and similar to those for related compounds (Dimmock et al., 1999, 2002).
It may be noted that a polymorph of (I) [Cambridge Structural Database (CSD; Groom et al., 2016) refcode VENQUA; Dimmock et al., 1999] has been reported in the same i.e. P21/c; VENQUA was recrystallized from methanol solution rather than ethanol for (I). The bond lengths and angles in (I) and VENQUA are very similar, although there is a ∼10° difference in the dihedral angle between the benzene rings [value for VENQUA = 35.88 (11)°, calculated with PLATON (Spek, 2009)]; for an overlay plot of (I) and VENQUA, see the supporting information.
3. Supramolecular features
There are obviously no classical hydrogen bonds in these structures and, in each case, just one C—H group can be identified as the donor for a weak hydrogen bond with atom O1 as the acceptor in (I)–(IV) and atom N1 in (V); geometrical data for these interactions are listed in Tables 1–5 and illustrated in Figs. 7–11. All the structures also feature weak C—H⋯π interactions with either the fused or pendant benzene rings as acceptors, but (II) and (III) are the only structures to display weak aromatic π–π stacking, in both cases between inversion-related C13–C18 rings. For (II), the centroid–centroid separation is 3.8414 (7) Å and the slippage is 1.72 Å; equivalent data for (III) are 3.9475 (7) and 1.89 Å, respectively.
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The packing motifs for the extended structures of (I) and (III) are infinite C—H⋯O hydrogen-bonded chains, which propagate in the [010] and [100] directions, respectively. In each case, adjacent molecules are related only by unit-cell translational symmetry and a C(8) graph-set motif results for both structures with the methyne group (C15—H15, ortho to the 4-substituent) involved as the donor.
The packing motifs for (II) and (IV) feature inversion dimers. In (II), C18—H18 (meta to the 4-substituent) is the donor group and R22(14) loops arise. In this motif, C12—H12 is `sandwiched' between the donor and acceptor and the H12⋯O1 separation of 2.60 Å (see Fig. 8) is borderline to be regarded as a directional bond. The donor group in (IV) is C10—H10 in the fused benzene ring, which generates an R22(10) loop. The only possible interaction involving the Cl atom is a long contact from C8—H8, with H⋯Cl = 2.93 Å. The presence of the cyano group in (V) allows for the formation of pairwise C—H⋯N hydrogen bonds and an R22(10) graph-set motif arises; the shortest H⋯O contact in (V) is 2.72 Å.
Rather than the C(8) chains arising from C15—H15⋯O1 hydrogen bonds seen in (I), the packing for VENQUA (see above) features inversion dimers built from pairwise C10—H10⋯O1 interactions, which are very similar to those seen in 4-chloro derivative (IV) in the present study. It may be noted that the density of VENQUA (ρ = 1.368 Mg m−3) is significantly greater than that of (I) (ρ = 1.284 Mg m−3), suggesting that the former might be the more stable polymorph if the `rational packing rule' (Kitaigorodskii, 1961) is applicable in this case.
In order to gain further insight into these different packing motifs, the Hirshfeld surfaces and fingerprint plots for (I) and VENQUA were calculated using CrystalExplorer (Turner et al., 2017), following the approach recently described by Tan et al. (2019). The Hirshfeld surface for (I) (see supporting information) shows the expected large red spots (close contacts) in the vicinity of H15 and O1 corresponding to the C15—H15⋯O1 interaction noted above, but there is little if any evidence of close contacts in the vicinity of H19A and H19C corresponding to the C—H⋯π contacts listed in Table 1. The surface for VENQUA (see supporting information) shows red spots in the vicinity of H10 and O1 corresponding to the C10—H10⋯O1 hydrogen bond and H2A (our numbering scheme) corresponding to a C3—H2A⋯π interaction (H⋯π = 2.69 Å) to the centroid of the C6–C11 benzene ring, but there are also probably spurious features close to H8 and H17 corresponding to a short H⋯H contact of 2.07 Å between these atoms, which possibly arose because the H atoms of the C19 methyl group in VENQUA were geometrically placed and not treated using a rotating-group model. Notwithstanding this, the fingerprint plots for (I) and VENQUA (see supporting information) decomposed into the different percentage contact types (Table 6) are almost identical; H⋯H (van der Waals) contacts dominate both structures, followed by C⋯H/H⋯C and then O⋯H/H⋯O. The percentage contributions of the other contact types are negligible.
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4. Database survey
A survey of the Cambridge Structural Database (CSD; Groom et al., 2016) revealed 167 structures incorporating a 1-benzosuberone fragment but only 20 hits when an exocyclic C=C double bond at the 2-position was added to the search structure. The key papers reporting the structures of closely related, differently substituted, 2-benzylidene-1-benzosuberones are Dimmock et al. (1999, 2002). The hydrogen-bond data for (I)–(V) and the 12 structures reported in the two papers by Dimmock et al. are summarized in Table 7. The most frequently observed motif is the centrosymmetric R22(10) loop involving C10—H10 as the donor group, but there are many others involving different C—H groups as donor and we see no obvious connection to the nature and position of the substituent(s) on the remote benzene ring. There are no structures in which the fused and pendant benzene rings tend towards being perpendicular (dihedral angle > 60°).
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The fact that (I) and VENQUA have similar conformations but distinct packing motifs mediated by different C—H⋯O interactions to the same acceptor O atom may be compared with the fascinating recent survey of weak-interaction polymorphs by Lo Presti (2018). He concluded that weak hydrogen bonds and solvent effects may play an important kinetic role in promoting polymorph formation (after all, something has to favour a situation where the lowest-energy packing motif is not adopted) but they do not play a dominant energetic role in polymorph formation and that the overall energy balance between dispersive (attractive) and repulsive interactions is the most important consideration.
5. Synthesis and crystallization
Compounds (I)–(V) were obtained from the reaction of 1-benzosuberone (1 mmol) with the appropriate 4-substituted benzaldehyde (1 mmol) in ethanol (5 ml) treated with an ethanolic solution of sodium hydroxide (30 mg in 5 ml ethanol). After stirring for 3–4 h at room temperature, each reaction mixture was cooled to 0 °C and the precipitated solid was recovered by filtration and rinsing with ice-cold ethanol. Recrystallization from ethanol solution at room temperature yielded colourless blocks [(I), (III) and (V)] and plates [(II) and (IV)]. Spectroscopic data for (I)–(V) are available as supporting information.
6. Refinement
Crystal data, data collection and structure . All H atoms were located geometrically (C—H = 0.95–0.99 Å) and refined as riding atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups in (I) and (II) were allowed to rotate, but not to tip, to best fit the electron density.
details are summarized in Table 8
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Supporting information
https://doi.org/10.1107/S2056989019014245/eb2024sup1.cif
contains datablocks I, II, III, IV, V, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019014245/eb2024Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019014245/eb2024IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989019014245/eb2024IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989019014245/eb2024IVsup5.hkl
Structure factors: contains datablock V. DOI: https://doi.org/10.1107/S2056989019014245/eb2024Vsup6.hkl
For all structures, data collection: CrysAlis PRO (Rigaku, 2017); cell
CrysAlis PRO (Rigaku, 2017); data reduction: CrysAlis PRO (Rigaku, 2017); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).C19H18O2 | F(000) = 592 |
Mr = 278.33 | Dx = 1.284 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9171 (3) Å | Cell parameters from 6994 reflections |
b = 9.1262 (2) Å | θ = 3.6–30.6° |
c = 15.2539 (3) Å | µ = 0.08 mm−1 |
β = 108.618 (3)° | T = 100 K |
V = 1440.24 (6) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.15 × 0.05 mm |
XtaLAB AFC12 (RCD3): Kappa single CCD diffractometer | 3296 independent reflections |
Radiation source: Rotating-anode X-ray tube | 2843 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017) | h = −13→14 |
Tmin = 0.877, Tmax = 1.000 | k = −11→11 |
16988 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0435P)2 + 0.435P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3296 reflections | Δρmax = 0.25 e Å−3 |
191 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
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 | ||
C1 | 0.21223 (10) | 0.67551 (12) | 0.33073 (7) | 0.0185 (2) | |
C2 | 0.25289 (10) | 0.51984 (12) | 0.35285 (7) | 0.0176 (2) | |
C3 | 0.26700 (10) | 0.42493 (12) | 0.27568 (7) | 0.0192 (2) | |
H3A | 0.3201 | 0.3384 | 0.3032 | 0.023* | |
H3B | 0.3146 | 0.4809 | 0.2413 | 0.023* | |
C4 | 0.13905 (11) | 0.37140 (12) | 0.20672 (7) | 0.0235 (2) | |
H4A | 0.1543 | 0.3392 | 0.1491 | 0.028* | |
H4B | 0.1077 | 0.2858 | 0.2333 | 0.028* | |
C5 | 0.03505 (11) | 0.49088 (12) | 0.18348 (8) | 0.0228 (2) | |
H5A | −0.0381 | 0.4586 | 0.1296 | 0.027* | |
H5B | 0.0022 | 0.5024 | 0.2365 | 0.027* | |
C6 | 0.08193 (10) | 0.63762 (12) | 0.16175 (7) | 0.0187 (2) | |
C7 | 0.03877 (11) | 0.69424 (13) | 0.07205 (7) | 0.0220 (2) | |
H7 | −0.0170 | 0.6369 | 0.0237 | 0.026* | |
C8 | 0.07549 (11) | 0.83208 (13) | 0.05212 (8) | 0.0237 (2) | |
H8 | 0.0461 | 0.8677 | −0.0096 | 0.028* | |
C9 | 0.15527 (11) | 0.91857 (13) | 0.12212 (8) | 0.0227 (2) | |
H9 | 0.1795 | 1.0139 | 0.1087 | 0.027* | |
C10 | 0.19928 (10) | 0.86472 (12) | 0.21178 (7) | 0.0199 (2) | |
H10 | 0.2534 | 0.9237 | 0.2600 | 0.024* | |
C11 | 0.16467 (10) | 0.72442 (12) | 0.23167 (7) | 0.0178 (2) | |
C12 | 0.28541 (10) | 0.48266 (12) | 0.44276 (7) | 0.0184 (2) | |
H12 | 0.2785 | 0.5598 | 0.4828 | 0.022* | |
C13 | 0.32958 (10) | 0.34296 (12) | 0.48884 (7) | 0.0179 (2) | |
C14 | 0.28868 (10) | 0.20616 (12) | 0.44938 (7) | 0.0186 (2) | |
H14 | 0.2300 | 0.2016 | 0.3881 | 0.022* | |
C15 | 0.33124 (10) | 0.07653 (12) | 0.49704 (7) | 0.0192 (2) | |
H15 | 0.3014 | −0.0152 | 0.4689 | 0.023* | |
C16 | 0.41828 (10) | 0.08253 (12) | 0.58673 (7) | 0.0182 (2) | |
C17 | 0.45955 (10) | 0.21776 (12) | 0.62786 (7) | 0.0205 (2) | |
H17 | 0.5189 | 0.2220 | 0.6889 | 0.025* | |
C18 | 0.41448 (11) | 0.34552 (12) | 0.58016 (7) | 0.0204 (2) | |
H18 | 0.4414 | 0.4371 | 0.6096 | 0.024* | |
C19 | 0.41639 (11) | −0.17646 (12) | 0.60092 (8) | 0.0220 (2) | |
H19A | 0.3224 | −0.1777 | 0.5874 | 0.033* | |
H19B | 0.4555 | −0.2544 | 0.6452 | 0.033* | |
H19C | 0.4370 | −0.1924 | 0.5436 | 0.033* | |
O1 | 0.21902 (8) | 0.76586 (9) | 0.39153 (5) | 0.0253 (2) | |
O2 | 0.46646 (7) | −0.03768 (8) | 0.63967 (5) | 0.02142 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0175 (5) | 0.0198 (5) | 0.0189 (5) | −0.0002 (4) | 0.0067 (4) | −0.0003 (4) |
C2 | 0.0171 (5) | 0.0181 (5) | 0.0178 (5) | −0.0003 (4) | 0.0058 (4) | −0.0001 (4) |
C3 | 0.0236 (6) | 0.0186 (5) | 0.0166 (5) | 0.0020 (4) | 0.0081 (4) | 0.0007 (4) |
C4 | 0.0305 (6) | 0.0199 (6) | 0.0183 (5) | −0.0024 (5) | 0.0054 (5) | −0.0002 (4) |
C5 | 0.0215 (6) | 0.0247 (6) | 0.0204 (5) | −0.0040 (4) | 0.0041 (4) | 0.0002 (4) |
C6 | 0.0165 (5) | 0.0211 (5) | 0.0192 (5) | 0.0020 (4) | 0.0065 (4) | 0.0011 (4) |
C7 | 0.0195 (5) | 0.0265 (6) | 0.0186 (5) | 0.0036 (4) | 0.0041 (4) | 0.0004 (4) |
C8 | 0.0246 (6) | 0.0283 (6) | 0.0192 (5) | 0.0083 (5) | 0.0083 (4) | 0.0070 (4) |
C9 | 0.0250 (6) | 0.0203 (6) | 0.0260 (6) | 0.0048 (4) | 0.0127 (5) | 0.0057 (4) |
C10 | 0.0196 (5) | 0.0194 (5) | 0.0220 (5) | 0.0027 (4) | 0.0086 (4) | −0.0001 (4) |
C11 | 0.0174 (5) | 0.0192 (5) | 0.0182 (5) | 0.0032 (4) | 0.0076 (4) | 0.0015 (4) |
C12 | 0.0187 (5) | 0.0193 (5) | 0.0181 (5) | 0.0003 (4) | 0.0070 (4) | −0.0014 (4) |
C13 | 0.0177 (5) | 0.0213 (5) | 0.0159 (5) | 0.0009 (4) | 0.0071 (4) | 0.0008 (4) |
C14 | 0.0178 (5) | 0.0233 (6) | 0.0142 (5) | −0.0003 (4) | 0.0042 (4) | 0.0008 (4) |
C15 | 0.0200 (5) | 0.0204 (5) | 0.0175 (5) | −0.0015 (4) | 0.0065 (4) | −0.0002 (4) |
C16 | 0.0179 (5) | 0.0218 (5) | 0.0163 (5) | 0.0027 (4) | 0.0076 (4) | 0.0037 (4) |
C17 | 0.0193 (5) | 0.0271 (6) | 0.0140 (5) | 0.0004 (4) | 0.0037 (4) | 0.0003 (4) |
C18 | 0.0222 (5) | 0.0218 (5) | 0.0176 (5) | −0.0011 (4) | 0.0071 (4) | −0.0024 (4) |
C19 | 0.0241 (6) | 0.0199 (5) | 0.0226 (5) | 0.0015 (4) | 0.0081 (4) | 0.0041 (4) |
O1 | 0.0349 (5) | 0.0208 (4) | 0.0187 (4) | 0.0036 (3) | 0.0066 (3) | −0.0019 (3) |
O2 | 0.0239 (4) | 0.0209 (4) | 0.0177 (4) | 0.0025 (3) | 0.0043 (3) | 0.0037 (3) |
C1—O1 | 1.2254 (13) | C9—H9 | 0.9500 |
C1—C2 | 1.4945 (15) | C10—C11 | 1.3955 (15) |
C1—C11 | 1.5003 (14) | C10—H10 | 0.9500 |
C2—C12 | 1.3458 (15) | C12—C13 | 1.4614 (15) |
C2—C3 | 1.5085 (14) | C12—H12 | 0.9500 |
C3—C4 | 1.5356 (15) | C13—C14 | 1.3959 (15) |
C3—H3A | 0.9900 | C13—C18 | 1.4056 (15) |
C3—H3B | 0.9900 | C14—C15 | 1.3887 (15) |
C4—C5 | 1.5319 (16) | C14—H14 | 0.9500 |
C4—H4A | 0.9900 | C15—C16 | 1.3956 (15) |
C4—H4B | 0.9900 | C15—H15 | 0.9500 |
C5—C6 | 1.5078 (15) | C16—O2 | 1.3642 (12) |
C5—H5A | 0.9900 | C16—C17 | 1.3926 (15) |
C5—H5B | 0.9900 | C17—C18 | 1.3793 (15) |
C6—C7 | 1.3962 (15) | C17—H17 | 0.9500 |
C6—C11 | 1.4021 (15) | C18—H18 | 0.9500 |
C7—C8 | 1.3832 (16) | C19—O2 | 1.4304 (13) |
C7—H7 | 0.9500 | C19—H19A | 0.9800 |
C8—C9 | 1.3885 (17) | C19—H19B | 0.9800 |
C8—H8 | 0.9500 | C19—H19C | 0.9800 |
C9—C10 | 1.3869 (15) | ||
O1—C1—C2 | 121.79 (10) | C8—C9—H9 | 120.3 |
O1—C1—C11 | 118.68 (10) | C9—C10—C11 | 120.47 (11) |
C2—C1—C11 | 119.51 (9) | C9—C10—H10 | 119.8 |
C12—C2—C1 | 115.63 (9) | C11—C10—H10 | 119.8 |
C12—C2—C3 | 126.23 (10) | C10—C11—C6 | 120.42 (10) |
C1—C2—C3 | 117.81 (9) | C10—C11—C1 | 117.47 (10) |
C2—C3—C4 | 114.83 (9) | C6—C11—C1 | 121.99 (9) |
C2—C3—H3A | 108.6 | C2—C12—C13 | 130.49 (10) |
C4—C3—H3A | 108.6 | C2—C12—H12 | 114.8 |
C2—C3—H3B | 108.6 | C13—C12—H12 | 114.8 |
C4—C3—H3B | 108.6 | C14—C13—C18 | 117.46 (10) |
H3A—C3—H3B | 107.5 | C14—C13—C12 | 124.18 (9) |
C5—C4—C3 | 112.15 (9) | C18—C13—C12 | 118.30 (10) |
C5—C4—H4A | 109.2 | C15—C14—C13 | 121.92 (10) |
C3—C4—H4A | 109.2 | C15—C14—H14 | 119.0 |
C5—C4—H4B | 109.2 | C13—C14—H14 | 119.0 |
C3—C4—H4B | 109.2 | C14—C15—C16 | 119.28 (10) |
H4A—C4—H4B | 107.9 | C14—C15—H15 | 120.4 |
C6—C5—C4 | 113.86 (9) | C16—C15—H15 | 120.4 |
C6—C5—H5A | 108.8 | O2—C16—C17 | 115.97 (9) |
C4—C5—H5A | 108.8 | O2—C16—C15 | 124.19 (10) |
C6—C5—H5B | 108.8 | C17—C16—C15 | 119.84 (10) |
C4—C5—H5B | 108.8 | C18—C17—C16 | 120.12 (10) |
H5A—C5—H5B | 107.7 | C18—C17—H17 | 119.9 |
C7—C6—C11 | 118.05 (10) | C16—C17—H17 | 119.9 |
C7—C6—C5 | 120.80 (10) | C17—C18—C13 | 121.34 (10) |
C11—C6—C5 | 121.07 (9) | C17—C18—H18 | 119.3 |
C8—C7—C6 | 121.41 (11) | C13—C18—H18 | 119.3 |
C8—C7—H7 | 119.3 | O2—C19—H19A | 109.5 |
C6—C7—H7 | 119.3 | O2—C19—H19B | 109.5 |
C7—C8—C9 | 120.18 (10) | H19A—C19—H19B | 109.5 |
C7—C8—H8 | 119.9 | O2—C19—H19C | 109.5 |
C9—C8—H8 | 119.9 | H19A—C19—H19C | 109.5 |
C10—C9—C8 | 119.45 (11) | H19B—C19—H19C | 109.5 |
C10—C9—H9 | 120.3 | C16—O2—C19 | 116.31 (8) |
O1—C1—C2—C12 | 6.07 (15) | O1—C1—C11—C10 | 36.06 (14) |
C11—C1—C2—C12 | −175.42 (9) | C2—C1—C11—C10 | −142.50 (10) |
O1—C1—C2—C3 | −167.73 (10) | O1—C1—C11—C6 | −140.03 (11) |
C11—C1—C2—C3 | 10.78 (14) | C2—C1—C11—C6 | 41.42 (14) |
C12—C2—C3—C4 | 110.47 (12) | C1—C2—C12—C13 | −179.67 (10) |
C1—C2—C3—C4 | −76.47 (12) | C3—C2—C12—C13 | −6.47 (19) |
C2—C3—C4—C5 | 40.48 (13) | C2—C12—C13—C14 | −33.81 (17) |
C3—C4—C5—C6 | 46.53 (12) | C2—C12—C13—C18 | 148.98 (11) |
C4—C5—C6—C7 | 110.60 (11) | C18—C13—C14—C15 | −1.16 (15) |
C4—C5—C6—C11 | −72.74 (13) | C12—C13—C14—C15 | −178.38 (10) |
C11—C6—C7—C8 | −0.30 (16) | C13—C14—C15—C16 | −0.55 (15) |
C5—C6—C7—C8 | 176.46 (10) | C14—C15—C16—O2 | −179.87 (9) |
C6—C7—C8—C9 | −1.05 (17) | C14—C15—C16—C17 | 1.11 (15) |
C7—C8—C9—C10 | 0.97 (16) | O2—C16—C17—C18 | −179.03 (9) |
C8—C9—C10—C11 | 0.46 (16) | C15—C16—C17—C18 | 0.07 (15) |
C9—C10—C11—C6 | −1.83 (15) | C16—C17—C18—C13 | −1.85 (16) |
C9—C10—C11—C1 | −177.98 (9) | C14—C13—C18—C17 | 2.36 (15) |
C7—C6—C11—C10 | 1.73 (15) | C12—C13—C18—C17 | 179.75 (9) |
C5—C6—C11—C10 | −175.02 (10) | C17—C16—O2—C19 | 174.98 (9) |
C7—C6—C11—C1 | 177.70 (9) | C15—C16—O2—C19 | −4.07 (14) |
C5—C6—C11—C1 | 0.95 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1i | 0.95 | 2.35 | 3.2971 (14) | 176 |
C19—H19A···Cg1ii | 0.98 | 2.76 | 3.6165 (13) | 146 |
C19—H19C···Cg2iii | 0.98 | 2.74 | 3.6029 (13) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y, −z+1. |
C20H20O2 | F(000) = 624 |
Mr = 292.36 | Dx = 1.291 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 12.6208 (2) Å | Cell parameters from 4578 reflections |
b = 14.99690 (17) Å | θ = 3.7–69.7° |
c = 8.39151 (12) Å | µ = 0.64 mm−1 |
β = 108.6814 (17)° | T = 100 K |
V = 1504.60 (4) Å3 | Plate, colourless |
Z = 4 | 0.20 × 0.11 × 0.03 mm |
XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer | 2704 independent reflections |
Radiation source: Rotating-anode X-ray tube | 2486 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.024 |
ω scans | θmax = 68.3°, θmin = 3.7° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku, 2017) | h = −14→15 |
Tmin = 0.772, Tmax = 1.000 | k = −18→12 |
9197 measured reflections | l = −9→9 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.4554P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.25 e Å−3 |
2704 reflections | Δρmin = −0.20 e Å−3 |
201 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0019 (3) |
Primary atom site location: structure-invariant direct methods |
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 | ||
C1 | 0.29882 (10) | 0.41642 (7) | 0.43555 (14) | 0.0187 (3) | |
C2 | 0.34088 (9) | 0.37739 (8) | 0.60870 (14) | 0.0181 (3) | |
C3 | 0.27266 (9) | 0.30342 (8) | 0.64912 (14) | 0.0183 (3) | |
H3A | 0.3219 | 0.2668 | 0.7414 | 0.022* | |
H3B | 0.2438 | 0.2646 | 0.5492 | 0.022* | |
C4 | 0.17406 (9) | 0.33720 (8) | 0.70118 (14) | 0.0196 (3) | |
H4A | 0.2021 | 0.3603 | 0.8178 | 0.024* | |
H4B | 0.1226 | 0.2870 | 0.6990 | 0.024* | |
C5 | 0.10987 (10) | 0.41143 (8) | 0.58327 (14) | 0.0203 (3) | |
H5A | 0.0363 | 0.4193 | 0.6001 | 0.024* | |
H5B | 0.1517 | 0.4680 | 0.6155 | 0.024* | |
C6 | 0.09109 (10) | 0.39437 (7) | 0.39855 (14) | 0.0187 (3) | |
C7 | −0.01602 (10) | 0.37634 (8) | 0.28964 (15) | 0.0218 (3) | |
H7 | −0.0757 | 0.3683 | 0.3342 | 0.026* | |
C8 | −0.03708 (10) | 0.36985 (8) | 0.11691 (15) | 0.0239 (3) | |
H8 | −0.1104 | 0.3564 | 0.0451 | 0.029* | |
C9 | 0.04853 (10) | 0.38295 (8) | 0.04913 (15) | 0.0233 (3) | |
H9 | 0.0337 | 0.3808 | −0.0692 | 0.028* | |
C10 | 0.15569 (10) | 0.39914 (8) | 0.15573 (14) | 0.0201 (3) | |
H10 | 0.2145 | 0.4080 | 0.1097 | 0.024* | |
C11 | 0.17889 (10) | 0.40265 (7) | 0.33013 (14) | 0.0183 (3) | |
C12 | 0.43722 (9) | 0.41219 (8) | 0.71077 (14) | 0.0182 (3) | |
H12 | 0.4688 | 0.4565 | 0.6587 | 0.022* | |
C13 | 0.50252 (10) | 0.39471 (7) | 0.88640 (14) | 0.0183 (3) | |
C14 | 0.46487 (10) | 0.35195 (8) | 1.00672 (15) | 0.0207 (3) | |
H14 | 0.3911 | 0.3284 | 0.9737 | 0.025* | |
C15 | 0.53262 (10) | 0.34296 (8) | 1.17341 (15) | 0.0209 (3) | |
H15 | 0.5052 | 0.3134 | 1.2523 | 0.025* | |
C16 | 0.64063 (10) | 0.37742 (7) | 1.22393 (14) | 0.0186 (3) | |
C17 | 0.67988 (9) | 0.42064 (8) | 1.10640 (14) | 0.0193 (3) | |
H17 | 0.7537 | 0.4441 | 1.1399 | 0.023* | |
C18 | 0.61171 (10) | 0.42937 (8) | 0.94187 (14) | 0.0186 (3) | |
H18 | 0.6393 | 0.4597 | 0.8639 | 0.022* | |
C19 | 0.67659 (10) | 0.33225 (8) | 1.51117 (15) | 0.0229 (3) | |
H19A | 0.6531 | 0.2700 | 1.4798 | 0.028* | |
H19B | 0.6122 | 0.3655 | 1.5247 | 0.028* | |
C20 | 0.77366 (11) | 0.33441 (9) | 1.67216 (15) | 0.0271 (3) | |
H20A | 0.7515 | 0.3069 | 1.7626 | 0.041* | |
H20B | 0.7960 | 0.3964 | 1.7018 | 0.041* | |
H20C | 0.8367 | 0.3014 | 1.6569 | 0.041* | |
O1 | 0.36138 (7) | 0.45674 (6) | 0.37458 (10) | 0.0264 (2) | |
O2 | 0.71428 (7) | 0.37337 (6) | 1.38349 (10) | 0.0217 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0219 (6) | 0.0195 (6) | 0.0159 (6) | −0.0012 (4) | 0.0076 (5) | −0.0007 (4) |
C2 | 0.0192 (6) | 0.0212 (6) | 0.0155 (6) | 0.0017 (4) | 0.0077 (5) | 0.0005 (4) |
C3 | 0.0182 (6) | 0.0208 (6) | 0.0155 (5) | −0.0006 (4) | 0.0049 (4) | 0.0011 (4) |
C4 | 0.0195 (6) | 0.0250 (6) | 0.0154 (5) | −0.0014 (5) | 0.0071 (5) | 0.0005 (4) |
C5 | 0.0196 (6) | 0.0251 (6) | 0.0171 (6) | 0.0020 (5) | 0.0072 (5) | −0.0011 (4) |
C6 | 0.0204 (6) | 0.0187 (5) | 0.0171 (6) | 0.0027 (4) | 0.0059 (5) | 0.0012 (4) |
C7 | 0.0203 (6) | 0.0255 (6) | 0.0203 (6) | 0.0027 (5) | 0.0073 (5) | −0.0004 (5) |
C8 | 0.0197 (6) | 0.0297 (6) | 0.0195 (6) | 0.0019 (5) | 0.0023 (5) | −0.0015 (5) |
C9 | 0.0260 (6) | 0.0279 (6) | 0.0144 (6) | 0.0027 (5) | 0.0045 (5) | −0.0007 (5) |
C10 | 0.0233 (6) | 0.0213 (6) | 0.0169 (6) | 0.0008 (5) | 0.0081 (5) | 0.0007 (4) |
C11 | 0.0205 (6) | 0.0173 (5) | 0.0167 (6) | 0.0004 (4) | 0.0056 (5) | 0.0002 (4) |
C12 | 0.0184 (6) | 0.0207 (6) | 0.0176 (6) | 0.0010 (4) | 0.0087 (5) | 0.0007 (4) |
C13 | 0.0188 (6) | 0.0198 (5) | 0.0170 (6) | 0.0010 (4) | 0.0067 (5) | −0.0008 (4) |
C14 | 0.0169 (6) | 0.0258 (6) | 0.0195 (6) | −0.0022 (5) | 0.0063 (5) | 0.0001 (5) |
C15 | 0.0216 (6) | 0.0254 (6) | 0.0175 (6) | −0.0014 (5) | 0.0090 (5) | 0.0022 (4) |
C16 | 0.0202 (6) | 0.0200 (6) | 0.0149 (6) | 0.0026 (4) | 0.0049 (5) | −0.0009 (4) |
C17 | 0.0174 (6) | 0.0220 (6) | 0.0187 (6) | −0.0008 (4) | 0.0060 (5) | −0.0012 (4) |
C18 | 0.0205 (6) | 0.0199 (6) | 0.0173 (6) | 0.0003 (4) | 0.0089 (5) | 0.0002 (4) |
C19 | 0.0277 (6) | 0.0260 (6) | 0.0160 (6) | −0.0015 (5) | 0.0084 (5) | 0.0017 (5) |
C20 | 0.0329 (7) | 0.0287 (7) | 0.0174 (6) | −0.0010 (5) | 0.0049 (5) | 0.0016 (5) |
O1 | 0.0244 (5) | 0.0366 (5) | 0.0183 (4) | −0.0081 (4) | 0.0071 (3) | 0.0043 (4) |
O2 | 0.0207 (4) | 0.0296 (5) | 0.0137 (4) | −0.0018 (3) | 0.0041 (3) | 0.0025 (3) |
C1—O1 | 1.2286 (14) | C10—C11 | 1.3985 (16) |
C1—C2 | 1.4971 (16) | C10—H10 | 0.9500 |
C1—C11 | 1.5027 (16) | C12—C13 | 1.4635 (16) |
C2—C12 | 1.3481 (17) | C12—H12 | 0.9500 |
C2—C3 | 1.5079 (16) | C13—C14 | 1.4014 (16) |
C3—C4 | 1.5311 (15) | C13—C18 | 1.4053 (17) |
C3—H3A | 0.9900 | C14—C15 | 1.3927 (16) |
C3—H3B | 0.9900 | C14—H14 | 0.9500 |
C4—C5 | 1.5365 (16) | C15—C16 | 1.3909 (17) |
C4—H4A | 0.9900 | C15—H15 | 0.9500 |
C4—H4B | 0.9900 | C16—O2 | 1.3650 (14) |
C5—C6 | 1.5130 (16) | C16—C17 | 1.3968 (16) |
C5—H5A | 0.9900 | C17—C18 | 1.3794 (16) |
C5—H5B | 0.9900 | C17—H17 | 0.9500 |
C6—C7 | 1.3944 (17) | C18—H18 | 0.9500 |
C6—C11 | 1.4074 (16) | C19—O2 | 1.4426 (14) |
C7—C8 | 1.3908 (17) | C19—C20 | 1.5056 (17) |
C7—H7 | 0.9500 | C19—H19A | 0.9900 |
C8—C9 | 1.3868 (18) | C19—H19B | 0.9900 |
C8—H8 | 0.9500 | C20—H20A | 0.9800 |
C9—C10 | 1.3832 (18) | C20—H20B | 0.9800 |
C9—H9 | 0.9500 | C20—H20C | 0.9800 |
O1—C1—C2 | 121.41 (10) | C11—C10—H10 | 119.4 |
O1—C1—C11 | 118.88 (10) | C10—C11—C6 | 119.69 (11) |
C2—C1—C11 | 119.65 (10) | C10—C11—C1 | 117.07 (10) |
C12—C2—C1 | 115.63 (10) | C6—C11—C1 | 123.24 (10) |
C12—C2—C3 | 127.28 (10) | C2—C12—C13 | 132.29 (11) |
C1—C2—C3 | 117.09 (10) | C2—C12—H12 | 113.9 |
C2—C3—C4 | 113.30 (9) | C13—C12—H12 | 113.9 |
C2—C3—H3A | 108.9 | C14—C13—C18 | 116.96 (11) |
C4—C3—H3A | 108.9 | C14—C13—C12 | 126.59 (11) |
C2—C3—H3B | 108.9 | C18—C13—C12 | 116.32 (10) |
C4—C3—H3B | 108.9 | C15—C14—C13 | 121.81 (11) |
H3A—C3—H3B | 107.7 | C15—C14—H14 | 119.1 |
C3—C4—C5 | 111.41 (9) | C13—C14—H14 | 119.1 |
C3—C4—H4A | 109.3 | C16—C15—C14 | 119.77 (11) |
C5—C4—H4A | 109.3 | C16—C15—H15 | 120.1 |
C3—C4—H4B | 109.3 | C14—C15—H15 | 120.1 |
C5—C4—H4B | 109.3 | O2—C16—C15 | 125.13 (10) |
H4A—C4—H4B | 108.0 | O2—C16—C17 | 115.41 (10) |
C6—C5—C4 | 114.49 (10) | C15—C16—C17 | 119.46 (11) |
C6—C5—H5A | 108.6 | C18—C17—C16 | 120.15 (11) |
C4—C5—H5A | 108.6 | C18—C17—H17 | 119.9 |
C6—C5—H5B | 108.6 | C16—C17—H17 | 119.9 |
C4—C5—H5B | 108.6 | C17—C18—C13 | 121.83 (10) |
H5A—C5—H5B | 107.6 | C17—C18—H18 | 119.1 |
C7—C6—C11 | 118.32 (11) | C13—C18—H18 | 119.1 |
C7—C6—C5 | 120.34 (11) | O2—C19—C20 | 106.86 (10) |
C11—C6—C5 | 121.17 (10) | O2—C19—H19A | 110.3 |
C8—C7—C6 | 121.21 (11) | C20—C19—H19A | 110.3 |
C8—C7—H7 | 119.4 | O2—C19—H19B | 110.3 |
C6—C7—H7 | 119.4 | C20—C19—H19B | 110.3 |
C9—C8—C7 | 120.24 (11) | H19A—C19—H19B | 108.6 |
C9—C8—H8 | 119.9 | C19—C20—H20A | 109.5 |
C7—C8—H8 | 119.9 | C19—C20—H20B | 109.5 |
C10—C9—C8 | 119.24 (11) | H20A—C20—H20B | 109.5 |
C10—C9—H9 | 120.4 | C19—C20—H20C | 109.5 |
C8—C9—H9 | 120.4 | H20A—C20—H20C | 109.5 |
C9—C10—C11 | 121.14 (11) | H20B—C20—H20C | 109.5 |
C9—C10—H10 | 119.4 | C16—O2—C19 | 117.69 (9) |
O1—C1—C2—C12 | 20.55 (16) | O1—C1—C11—C10 | 27.78 (16) |
C11—C1—C2—C12 | −162.35 (10) | C2—C1—C11—C10 | −149.40 (11) |
O1—C1—C2—C3 | −158.66 (11) | O1—C1—C11—C6 | −151.50 (11) |
C11—C1—C2—C3 | 18.45 (15) | C2—C1—C11—C6 | 31.33 (16) |
C12—C2—C3—C4 | 97.96 (14) | C1—C2—C12—C13 | 177.92 (11) |
C1—C2—C3—C4 | −82.94 (12) | C3—C2—C12—C13 | −3.0 (2) |
C2—C3—C4—C5 | 45.35 (13) | C2—C12—C13—C14 | −17.9 (2) |
C3—C4—C5—C6 | 42.50 (13) | C2—C12—C13—C18 | 166.41 (12) |
C4—C5—C6—C7 | 110.32 (12) | C18—C13—C14—C15 | −0.80 (17) |
C4—C5—C6—C11 | −74.39 (14) | C12—C13—C14—C15 | −176.51 (11) |
C11—C6—C7—C8 | −2.33 (17) | C13—C14—C15—C16 | 0.32 (18) |
C5—C6—C7—C8 | 173.09 (11) | C14—C15—C16—O2 | 179.45 (11) |
C6—C7—C8—C9 | −1.20 (18) | C14—C15—C16—C17 | −0.06 (17) |
C7—C8—C9—C10 | 2.45 (18) | O2—C16—C17—C18 | −179.24 (10) |
C8—C9—C10—C11 | −0.12 (18) | C15—C16—C17—C18 | 0.32 (17) |
C9—C10—C11—C6 | −3.44 (17) | C16—C17—C18—C13 | −0.85 (17) |
C9—C10—C11—C1 | 177.26 (11) | C14—C13—C18—C17 | 1.07 (17) |
C7—C6—C11—C10 | 4.59 (16) | C12—C13—C18—C17 | 177.23 (10) |
C5—C6—C11—C10 | −170.79 (10) | C15—C16—O2—C19 | −1.70 (16) |
C7—C6—C11—C1 | −176.16 (11) | C17—C16—O2—C19 | 177.83 (10) |
C5—C6—C11—C1 | 8.46 (17) | C20—C19—O2—C16 | 178.58 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O1i | 0.95 | 2.36 | 3.2653 (14) | 159 |
C4—H4B···Cg1ii | 0.98 | 2.72 | 3.6429 (13) | 155 |
C19—H19A···Cg2ii | 0.98 | 2.71 | 3.5969 (13) | 149 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2. |
C25H22O2 | Z = 2 |
Mr = 354.42 | F(000) = 376 |
Triclinic, P1 | Dx = 1.285 Mg m−3 |
a = 9.2870 (2) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.8727 (2) Å | Cell parameters from 19041 reflections |
c = 12.2944 (3) Å | θ = 3.9–70.3° |
α = 67.098 (3)° | µ = 0.63 mm−1 |
β = 81.472 (2)° | T = 100 K |
γ = 61.989 (3)° | Block, colourless |
V = 915.92 (5) Å3 | 0.17 × 0.11 × 0.04 mm |
XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer | 3336 independent reflections |
Radiation source: Rotating-anode X-ray tube | 3073 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.036 |
ω scans | θmax = 68.2°, θmin = 3.9° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku, 2017) | h = −11→11 |
Tmin = 0.781, Tmax = 1.000 | k = −11→11 |
29818 measured reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0343P)2 + 0.2601P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.080 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.19 e Å−3 |
3336 reflections | Δρmin = −0.16 e Å−3 |
245 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0027 (4) |
Primary atom site location: structure-invariant direct methods |
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 | ||
C1 | −0.05094 (13) | 0.41786 (13) | 0.37210 (9) | 0.0206 (2) | |
C2 | 0.11044 (12) | 0.39278 (12) | 0.40498 (9) | 0.0201 (2) | |
C3 | 0.15112 (13) | 0.53459 (13) | 0.34098 (9) | 0.0218 (2) | |
H3A | 0.2299 | 0.5293 | 0.3905 | 0.026* | |
H3B | 0.0507 | 0.6397 | 0.3286 | 0.026* | |
C4 | 0.22435 (13) | 0.53175 (14) | 0.22121 (9) | 0.0253 (2) | |
H4A | 0.3404 | 0.4482 | 0.2340 | 0.030* | |
H4B | 0.2204 | 0.6406 | 0.1732 | 0.030* | |
C5 | 0.13332 (14) | 0.49174 (14) | 0.15296 (9) | 0.0261 (2) | |
H5A | 0.1675 | 0.5174 | 0.0702 | 0.031* | |
H5B | 0.1661 | 0.3720 | 0.1880 | 0.031* | |
C6 | −0.05030 (13) | 0.58461 (13) | 0.15292 (9) | 0.0232 (2) | |
C7 | −0.14024 (15) | 0.70291 (13) | 0.04850 (10) | 0.0286 (3) | |
H7 | −0.0846 | 0.7283 | −0.0221 | 0.034* | |
C8 | −0.30954 (15) | 0.78425 (14) | 0.04574 (10) | 0.0311 (3) | |
H8 | −0.3685 | 0.8652 | −0.0262 | 0.037* | |
C9 | −0.39279 (14) | 0.74770 (14) | 0.14755 (11) | 0.0295 (3) | |
H9 | −0.5087 | 0.8033 | 0.1457 | 0.035* | |
C10 | −0.30610 (13) | 0.62955 (13) | 0.25218 (10) | 0.0254 (2) | |
H10 | −0.3632 | 0.6033 | 0.3218 | 0.030* | |
C11 | −0.13575 (13) | 0.54864 (12) | 0.25643 (9) | 0.0214 (2) | |
C12 | 0.20322 (12) | 0.24621 (13) | 0.48767 (9) | 0.0203 (2) | |
H12 | 0.1549 | 0.1733 | 0.5162 | 0.024* | |
C13 | 0.36457 (13) | 0.17816 (13) | 0.54185 (9) | 0.0208 (2) | |
C14 | 0.48036 (13) | 0.23711 (13) | 0.49726 (9) | 0.0232 (2) | |
H14 | 0.4568 | 0.3274 | 0.4241 | 0.028* | |
C15 | 0.62886 (13) | 0.16712 (13) | 0.55709 (9) | 0.0239 (2) | |
H15 | 0.7051 | 0.2099 | 0.5253 | 0.029* | |
C16 | 0.66527 (12) | 0.03382 (13) | 0.66400 (9) | 0.0214 (2) | |
C17 | 0.55458 (13) | −0.03095 (12) | 0.70815 (9) | 0.0213 (2) | |
H17 | 0.5800 | −0.1236 | 0.7799 | 0.026* | |
C18 | 0.40818 (13) | 0.03976 (13) | 0.64743 (9) | 0.0211 (2) | |
H18 | 0.3344 | −0.0065 | 0.6779 | 0.025* | |
C19 | 0.92156 (13) | 0.02302 (14) | 0.68813 (10) | 0.0291 (3) | |
H19A | 0.8709 | 0.1402 | 0.6798 | 0.035* | |
H19B | 0.9567 | 0.0162 | 0.6096 | 0.035* | |
C20 | 1.06575 (13) | −0.07617 (13) | 0.77387 (9) | 0.0230 (2) | |
C21 | 1.18414 (13) | −0.22910 (13) | 0.77295 (10) | 0.0251 (2) | |
H21 | 1.1719 | −0.2709 | 0.7190 | 0.030* | |
C22 | 1.31964 (13) | −0.32064 (13) | 0.85007 (10) | 0.0266 (2) | |
H22 | 1.3985 | −0.4259 | 0.8499 | 0.032* | |
C23 | 1.34081 (13) | −0.25957 (14) | 0.92737 (10) | 0.0273 (3) | |
H23 | 1.4350 | −0.3216 | 0.9791 | 0.033* | |
C24 | 1.22388 (14) | −0.10747 (14) | 0.92885 (10) | 0.0283 (3) | |
H24 | 1.2376 | −0.0652 | 0.9819 | 0.034* | |
C25 | 1.08673 (13) | −0.01680 (13) | 0.85305 (10) | 0.0257 (2) | |
H25 | 1.0063 | 0.0868 | 0.8552 | 0.031* | |
O1 | −0.11776 (9) | 0.33551 (9) | 0.43769 (6) | 0.02637 (19) | |
O2 | 0.80574 (9) | −0.04221 (9) | 0.73220 (6) | 0.02490 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0216 (5) | 0.0216 (5) | 0.0211 (5) | −0.0107 (4) | 0.0026 (4) | −0.0097 (4) |
C2 | 0.0206 (5) | 0.0227 (5) | 0.0199 (5) | −0.0118 (4) | 0.0035 (4) | −0.0089 (4) |
C3 | 0.0214 (5) | 0.0210 (5) | 0.0235 (5) | −0.0110 (4) | 0.0009 (4) | −0.0069 (4) |
C4 | 0.0233 (6) | 0.0246 (5) | 0.0255 (6) | −0.0122 (5) | 0.0037 (4) | −0.0060 (4) |
C5 | 0.0296 (6) | 0.0267 (6) | 0.0219 (5) | −0.0135 (5) | 0.0058 (4) | −0.0094 (4) |
C6 | 0.0298 (6) | 0.0209 (5) | 0.0224 (5) | −0.0128 (5) | 0.0001 (4) | −0.0091 (4) |
C7 | 0.0407 (7) | 0.0254 (6) | 0.0226 (6) | −0.0172 (5) | −0.0016 (5) | −0.0077 (5) |
C8 | 0.0413 (7) | 0.0218 (6) | 0.0280 (6) | −0.0106 (5) | −0.0124 (5) | −0.0065 (5) |
C9 | 0.0269 (6) | 0.0248 (6) | 0.0362 (6) | −0.0062 (5) | −0.0092 (5) | −0.0140 (5) |
C10 | 0.0252 (6) | 0.0254 (6) | 0.0291 (6) | −0.0113 (5) | −0.0011 (4) | −0.0129 (5) |
C11 | 0.0240 (5) | 0.0197 (5) | 0.0232 (5) | −0.0101 (4) | −0.0012 (4) | −0.0096 (4) |
C12 | 0.0211 (5) | 0.0232 (5) | 0.0205 (5) | −0.0129 (4) | 0.0036 (4) | −0.0091 (4) |
C13 | 0.0208 (5) | 0.0212 (5) | 0.0219 (5) | −0.0097 (4) | 0.0017 (4) | −0.0092 (4) |
C14 | 0.0227 (5) | 0.0230 (5) | 0.0217 (5) | −0.0114 (4) | 0.0006 (4) | −0.0046 (4) |
C15 | 0.0226 (5) | 0.0256 (5) | 0.0243 (5) | −0.0144 (5) | 0.0030 (4) | −0.0063 (4) |
C16 | 0.0192 (5) | 0.0221 (5) | 0.0230 (5) | −0.0088 (4) | −0.0002 (4) | −0.0086 (4) |
C17 | 0.0223 (5) | 0.0197 (5) | 0.0210 (5) | −0.0105 (4) | 0.0011 (4) | −0.0055 (4) |
C18 | 0.0214 (5) | 0.0217 (5) | 0.0235 (5) | −0.0122 (4) | 0.0033 (4) | −0.0092 (4) |
C19 | 0.0242 (6) | 0.0305 (6) | 0.0307 (6) | −0.0183 (5) | −0.0022 (5) | −0.0008 (5) |
C20 | 0.0205 (5) | 0.0242 (5) | 0.0242 (5) | −0.0146 (4) | 0.0018 (4) | −0.0033 (4) |
C21 | 0.0288 (6) | 0.0261 (6) | 0.0255 (6) | −0.0174 (5) | 0.0023 (4) | −0.0088 (4) |
C22 | 0.0236 (6) | 0.0217 (5) | 0.0303 (6) | −0.0103 (5) | 0.0030 (4) | −0.0062 (5) |
C23 | 0.0236 (6) | 0.0296 (6) | 0.0250 (6) | −0.0153 (5) | −0.0030 (4) | −0.0009 (5) |
C24 | 0.0355 (6) | 0.0325 (6) | 0.0231 (6) | −0.0209 (5) | 0.0015 (5) | −0.0093 (5) |
C25 | 0.0260 (6) | 0.0224 (5) | 0.0273 (6) | −0.0115 (5) | 0.0056 (4) | −0.0085 (4) |
O1 | 0.0258 (4) | 0.0314 (4) | 0.0242 (4) | −0.0182 (3) | 0.0011 (3) | −0.0058 (3) |
O2 | 0.0201 (4) | 0.0269 (4) | 0.0257 (4) | −0.0141 (3) | −0.0028 (3) | −0.0019 (3) |
C1—O1 | 1.2294 (12) | C13—C14 | 1.4001 (14) |
C1—C2 | 1.4914 (14) | C13—C18 | 1.4042 (15) |
C1—C11 | 1.5025 (14) | C14—C15 | 1.3895 (15) |
C2—C12 | 1.3467 (15) | C14—H14 | 0.9500 |
C2—C3 | 1.5077 (14) | C15—C16 | 1.3933 (15) |
C3—C4 | 1.5326 (15) | C15—H15 | 0.9500 |
C3—H3A | 0.9900 | C16—O2 | 1.3723 (12) |
C3—H3B | 0.9900 | C16—C17 | 1.3936 (14) |
C4—C5 | 1.5352 (15) | C17—C18 | 1.3774 (14) |
C4—H4A | 0.9900 | C17—H17 | 0.9500 |
C4—H4B | 0.9900 | C18—H18 | 0.9500 |
C5—C6 | 1.5099 (15) | C19—O2 | 1.4392 (12) |
C5—H5A | 0.9900 | C19—C20 | 1.4990 (15) |
C5—H5B | 0.9900 | C19—H19A | 0.9900 |
C6—C7 | 1.3945 (15) | C19—H19B | 0.9900 |
C6—C11 | 1.4102 (15) | C20—C25 | 1.3916 (16) |
C7—C8 | 1.3881 (17) | C20—C21 | 1.3925 (16) |
C7—H7 | 0.9500 | C21—C22 | 1.3849 (16) |
C8—C9 | 1.3850 (18) | C21—H21 | 0.9500 |
C8—H8 | 0.9500 | C22—C23 | 1.3850 (16) |
C9—C10 | 1.3859 (16) | C22—H22 | 0.9500 |
C9—H9 | 0.9500 | C23—C24 | 1.3850 (17) |
C10—C11 | 1.3960 (15) | C23—H23 | 0.9500 |
C10—H10 | 0.9500 | C24—C25 | 1.3871 (16) |
C12—C13 | 1.4637 (14) | C24—H24 | 0.9500 |
C12—H12 | 0.9500 | C25—H25 | 0.9500 |
O1—C1—C2 | 121.81 (9) | C13—C12—H12 | 114.0 |
O1—C1—C11 | 118.85 (9) | C14—C13—C18 | 116.95 (9) |
C2—C1—C11 | 119.33 (9) | C14—C13—C12 | 125.98 (9) |
C12—C2—C1 | 116.43 (9) | C18—C13—C12 | 117.06 (9) |
C12—C2—C3 | 127.54 (9) | C15—C14—C13 | 121.79 (10) |
C1—C2—C3 | 116.03 (9) | C15—C14—H14 | 119.1 |
C2—C3—C4 | 111.93 (9) | C13—C14—H14 | 119.1 |
C2—C3—H3A | 109.2 | C14—C15—C16 | 119.59 (10) |
C4—C3—H3A | 109.2 | C14—C15—H15 | 120.2 |
C2—C3—H3B | 109.2 | C16—C15—H15 | 120.2 |
C4—C3—H3B | 109.2 | O2—C16—C15 | 124.70 (9) |
H3A—C3—H3B | 107.9 | O2—C16—C17 | 115.57 (9) |
C3—C4—C5 | 112.28 (9) | C15—C16—C17 | 119.73 (10) |
C3—C4—H4A | 109.1 | C18—C17—C16 | 119.83 (10) |
C5—C4—H4A | 109.1 | C18—C17—H17 | 120.1 |
C3—C4—H4B | 109.1 | C16—C17—H17 | 120.1 |
C5—C4—H4B | 109.1 | C17—C18—C13 | 122.01 (9) |
H4A—C4—H4B | 107.9 | C17—C18—H18 | 119.0 |
C6—C5—C4 | 114.06 (9) | C13—C18—H18 | 119.0 |
C6—C5—H5A | 108.7 | O2—C19—C20 | 108.38 (8) |
C4—C5—H5A | 108.7 | O2—C19—H19A | 110.0 |
C6—C5—H5B | 108.7 | C20—C19—H19A | 110.0 |
C4—C5—H5B | 108.7 | O2—C19—H19B | 110.0 |
H5A—C5—H5B | 107.6 | C20—C19—H19B | 110.0 |
C7—C6—C11 | 118.30 (10) | H19A—C19—H19B | 108.4 |
C7—C6—C5 | 120.45 (10) | C25—C20—C21 | 118.80 (10) |
C11—C6—C5 | 121.17 (9) | C25—C20—C19 | 121.35 (10) |
C8—C7—C6 | 121.25 (11) | C21—C20—C19 | 119.83 (10) |
C8—C7—H7 | 119.4 | C22—C21—C20 | 120.46 (10) |
C6—C7—H7 | 119.4 | C22—C21—H21 | 119.8 |
C9—C8—C7 | 120.17 (10) | C20—C21—H21 | 119.8 |
C9—C8—H8 | 119.9 | C21—C22—C23 | 120.37 (10) |
C7—C8—H8 | 119.9 | C21—C22—H22 | 119.8 |
C8—C9—C10 | 119.62 (11) | C23—C22—H22 | 119.8 |
C8—C9—H9 | 120.2 | C24—C23—C22 | 119.60 (10) |
C10—C9—H9 | 120.2 | C24—C23—H23 | 120.2 |
C9—C10—C11 | 120.72 (11) | C22—C23—H23 | 120.2 |
C9—C10—H10 | 119.6 | C23—C24—C25 | 120.12 (10) |
C11—C10—H10 | 119.6 | C23—C24—H24 | 119.9 |
C10—C11—C6 | 119.92 (10) | C25—C24—H24 | 119.9 |
C10—C11—C1 | 117.49 (9) | C24—C25—C20 | 120.64 (10) |
C6—C11—C1 | 122.50 (9) | C24—C25—H25 | 119.7 |
C2—C12—C13 | 132.05 (9) | C20—C25—H25 | 119.7 |
C2—C12—H12 | 114.0 | C16—O2—C19 | 116.40 (8) |
O1—C1—C2—C12 | 20.98 (15) | C3—C2—C12—C13 | 0.73 (19) |
C11—C1—C2—C12 | −159.81 (9) | C2—C12—C13—C14 | −17.70 (19) |
O1—C1—C2—C3 | −159.38 (10) | C2—C12—C13—C18 | 163.17 (11) |
C11—C1—C2—C3 | 19.82 (13) | C18—C13—C14—C15 | −2.86 (16) |
C12—C2—C3—C4 | 95.36 (13) | C12—C13—C14—C15 | 178.01 (10) |
C1—C2—C3—C4 | −84.23 (11) | C13—C14—C15—C16 | 0.48 (16) |
C2—C3—C4—C5 | 43.11 (12) | C14—C15—C16—O2 | −178.18 (10) |
C3—C4—C5—C6 | 45.09 (12) | C14—C15—C16—C17 | 1.83 (16) |
C4—C5—C6—C7 | 112.75 (11) | O2—C16—C17—C18 | 178.36 (9) |
C4—C5—C6—C11 | −70.46 (13) | C15—C16—C17—C18 | −1.65 (16) |
C11—C6—C7—C8 | 0.23 (16) | C16—C17—C18—C13 | −0.86 (16) |
C5—C6—C7—C8 | 177.11 (10) | C14—C13—C18—C17 | 3.06 (15) |
C6—C7—C8—C9 | −0.60 (17) | C12—C13—C18—C17 | −177.73 (9) |
C7—C8—C9—C10 | 0.04 (16) | O2—C19—C20—C25 | −102.31 (11) |
C8—C9—C10—C11 | 0.89 (16) | O2—C19—C20—C21 | 79.43 (12) |
C9—C10—C11—C6 | −1.26 (15) | C25—C20—C21—C22 | 0.41 (15) |
C9—C10—C11—C1 | −177.85 (9) | C19—C20—C21—C22 | 178.72 (9) |
C7—C6—C11—C10 | 0.69 (15) | C20—C21—C22—C23 | −1.38 (16) |
C5—C6—C11—C10 | −176.17 (9) | C21—C22—C23—C24 | 1.27 (16) |
C7—C6—C11—C1 | 177.10 (9) | C22—C23—C24—C25 | −0.20 (16) |
C5—C6—C11—C1 | 0.25 (15) | C23—C24—C25—C20 | −0.77 (16) |
O1—C1—C11—C10 | 32.34 (14) | C21—C20—C25—C24 | 0.67 (16) |
C2—C1—C11—C10 | −146.89 (10) | C19—C20—C25—C24 | −177.61 (10) |
O1—C1—C11—C6 | −144.16 (10) | C15—C16—O2—C19 | 0.07 (15) |
C2—C1—C11—C6 | 36.61 (14) | C17—C16—O2—C19 | −179.94 (9) |
C1—C2—C12—C13 | −179.68 (10) | C20—C19—O2—C16 | −179.68 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O1i | 0.95 | 2.40 | 3.3477 (13) | 176 |
C18—H18···Cg3ii | 0.95 | 2.64 | 3.5147 (13) | 153 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
C18H15ClO | F(000) = 592 |
Mr = 282.75 | Dx = 1.326 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.6273 (5) Å | Cell parameters from 4926 reflections |
b = 11.6191 (4) Å | θ = 4.8–70.0° |
c = 12.1114 (5) Å | µ = 2.31 mm−1 |
β = 108.777 (4)° | T = 100 K |
V = 1415.92 (11) Å3 | Plate, colourless |
Z = 4 | 0.28 × 0.20 × 0.03 mm |
XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer | 2568 independent reflections |
Radiation source: Rotating-anode X-ray tube | 2203 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.073 |
ω scans | θmax = 68.2°, θmin = 4.8° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku, 2017) | h = −12→11 |
Tmin = 0.722, Tmax = 1.000 | k = −13→13 |
11747 measured reflections | l = −14→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.1145P)2 + 0.0344P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
2568 reflections | Δρmax = 0.32 e Å−3 |
181 parameters | Δρmin = −0.41 e Å−3 |
0 restraints |
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 | ||
C1 | 0.2086 (2) | 0.65193 (16) | 0.58219 (17) | 0.0292 (4) | |
C2 | 0.34239 (19) | 0.67189 (16) | 0.67264 (17) | 0.0292 (4) | |
C3 | 0.34206 (19) | 0.73875 (16) | 0.77902 (17) | 0.0311 (5) | |
H3A | 0.4244 | 0.7207 | 0.8436 | 0.037* | |
H3B | 0.2658 | 0.7131 | 0.8029 | 0.037* | |
C4 | 0.3330 (2) | 0.86976 (16) | 0.76058 (18) | 0.0333 (5) | |
H4A | 0.4225 | 0.9004 | 0.7685 | 0.040* | |
H4B | 0.3028 | 0.9057 | 0.8218 | 0.040* | |
C5 | 0.2366 (2) | 0.90247 (17) | 0.64003 (18) | 0.0323 (5) | |
H5A | 0.2215 | 0.9866 | 0.6372 | 0.039* | |
H5B | 0.2775 | 0.8829 | 0.5796 | 0.039* | |
C6 | 0.1047 (2) | 0.84132 (17) | 0.61283 (17) | 0.0301 (5) | |
C7 | −0.0085 (2) | 0.90160 (19) | 0.61159 (17) | 0.0353 (5) | |
H7 | −0.0024 | 0.9820 | 0.6268 | 0.042* | |
C8 | −0.1309 (2) | 0.84680 (19) | 0.58856 (19) | 0.0367 (5) | |
H8 | −0.2071 | 0.8896 | 0.5885 | 0.044* | |
C9 | −0.1412 (2) | 0.72966 (19) | 0.56571 (17) | 0.0361 (5) | |
H9 | −0.2242 | 0.6917 | 0.5506 | 0.043* | |
C10 | −0.0297 (2) | 0.66851 (18) | 0.56509 (17) | 0.0330 (5) | |
H10 | −0.0369 | 0.5884 | 0.5486 | 0.040* | |
C11 | 0.09310 (19) | 0.72291 (16) | 0.58837 (16) | 0.0294 (5) | |
C12 | 0.4476 (2) | 0.62505 (16) | 0.65047 (18) | 0.0317 (5) | |
H12 | 0.4264 | 0.5825 | 0.5798 | 0.038* | |
C13 | 0.5893 (2) | 0.62893 (16) | 0.71748 (18) | 0.0303 (5) | |
C14 | 0.6506 (2) | 0.71561 (17) | 0.79718 (18) | 0.0334 (5) | |
H14 | 0.5983 | 0.7765 | 0.8116 | 0.040* | |
C15 | 0.7861 (2) | 0.71376 (17) | 0.85517 (18) | 0.0339 (5) | |
H15 | 0.8263 | 0.7730 | 0.9090 | 0.041* | |
C16 | 0.8629 (2) | 0.62534 (17) | 0.83450 (19) | 0.0341 (5) | |
C17 | 0.8062 (2) | 0.53886 (18) | 0.75589 (19) | 0.0391 (5) | |
H17 | 0.8593 | 0.4783 | 0.7421 | 0.047* | |
C18 | 0.6709 (2) | 0.54195 (18) | 0.69764 (18) | 0.0360 (5) | |
H18 | 0.6321 | 0.4833 | 0.6425 | 0.043* | |
O1 | 0.19203 (14) | 0.57880 (12) | 0.50600 (12) | 0.0347 (4) | |
Cl1 | 1.03346 (5) | 0.62611 (5) | 0.90563 (5) | 0.0469 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0308 (11) | 0.0267 (9) | 0.0297 (10) | −0.0017 (8) | 0.0091 (8) | 0.0023 (8) |
C2 | 0.0292 (10) | 0.0258 (9) | 0.0307 (10) | −0.0012 (7) | 0.0068 (8) | 0.0018 (7) |
C3 | 0.0273 (10) | 0.0325 (10) | 0.0309 (10) | 0.0007 (8) | 0.0056 (8) | −0.0006 (8) |
C4 | 0.0274 (11) | 0.0321 (11) | 0.0371 (12) | −0.0021 (8) | 0.0056 (9) | −0.0064 (8) |
C5 | 0.0308 (11) | 0.0277 (9) | 0.0362 (11) | −0.0004 (8) | 0.0076 (9) | −0.0006 (8) |
C6 | 0.0289 (11) | 0.0296 (10) | 0.0295 (10) | −0.0005 (8) | 0.0063 (8) | 0.0004 (8) |
C7 | 0.0330 (11) | 0.0362 (11) | 0.0330 (11) | 0.0017 (9) | 0.0056 (9) | −0.0004 (9) |
C8 | 0.0286 (11) | 0.0469 (12) | 0.0328 (11) | 0.0045 (9) | 0.0074 (9) | −0.0001 (9) |
C9 | 0.0289 (11) | 0.0455 (12) | 0.0312 (11) | −0.0047 (9) | 0.0059 (9) | 0.0015 (9) |
C10 | 0.0323 (11) | 0.0344 (11) | 0.0295 (10) | −0.0043 (8) | 0.0062 (8) | 0.0008 (8) |
C11 | 0.0280 (11) | 0.0318 (10) | 0.0263 (10) | 0.0004 (8) | 0.0058 (8) | 0.0017 (7) |
C12 | 0.0350 (12) | 0.0274 (10) | 0.0303 (11) | −0.0015 (8) | 0.0073 (9) | 0.0008 (7) |
C13 | 0.0306 (11) | 0.0317 (10) | 0.0284 (10) | 0.0020 (8) | 0.0090 (9) | 0.0025 (8) |
C14 | 0.0296 (11) | 0.0314 (10) | 0.0384 (11) | 0.0005 (8) | 0.0099 (9) | −0.0030 (8) |
C15 | 0.0325 (11) | 0.0338 (10) | 0.0350 (11) | −0.0023 (8) | 0.0101 (9) | −0.0016 (8) |
C16 | 0.0281 (11) | 0.0383 (11) | 0.0356 (12) | 0.0005 (8) | 0.0099 (9) | 0.0045 (8) |
C17 | 0.0339 (11) | 0.0373 (12) | 0.0465 (13) | 0.0049 (9) | 0.0134 (10) | −0.0025 (9) |
C18 | 0.0334 (11) | 0.0344 (11) | 0.0397 (12) | −0.0005 (8) | 0.0110 (9) | −0.0059 (8) |
O1 | 0.0348 (8) | 0.0318 (8) | 0.0354 (8) | −0.0029 (6) | 0.0083 (6) | −0.0060 (6) |
Cl1 | 0.0268 (4) | 0.0552 (4) | 0.0545 (4) | 0.0032 (2) | 0.0071 (3) | 0.0000 (2) |
C1—O1 | 1.225 (2) | C8—H8 | 0.9500 |
C1—C11 | 1.501 (3) | C9—C10 | 1.384 (3) |
C1—C2 | 1.507 (3) | C9—H9 | 0.9500 |
C2—C12 | 1.346 (3) | C10—C11 | 1.395 (3) |
C2—C3 | 1.506 (3) | C10—H10 | 0.9500 |
C3—C4 | 1.537 (3) | C12—C13 | 1.464 (3) |
C3—H3A | 0.9900 | C12—H12 | 0.9500 |
C3—H3B | 0.9900 | C13—C18 | 1.402 (3) |
C4—C5 | 1.537 (3) | C13—C14 | 1.402 (3) |
C4—H4A | 0.9900 | C14—C15 | 1.385 (3) |
C4—H4B | 0.9900 | C14—H14 | 0.9500 |
C5—C6 | 1.510 (3) | C15—C16 | 1.384 (3) |
C5—H5A | 0.9900 | C15—H15 | 0.9500 |
C5—H5B | 0.9900 | C16—C17 | 1.382 (3) |
C6—C7 | 1.388 (3) | C16—Cl1 | 1.739 (2) |
C6—C11 | 1.404 (3) | C17—C18 | 1.383 (3) |
C7—C8 | 1.393 (3) | C17—H17 | 0.9500 |
C7—H7 | 0.9500 | C18—H18 | 0.9500 |
C8—C9 | 1.386 (3) | ||
O1—C1—C11 | 119.82 (18) | C7—C8—H8 | 120.1 |
O1—C1—C2 | 121.84 (18) | C10—C9—C8 | 119.48 (19) |
C11—C1—C2 | 118.33 (16) | C10—C9—H9 | 120.3 |
C12—C2—C3 | 127.61 (18) | C8—C9—H9 | 120.3 |
C12—C2—C1 | 116.26 (17) | C9—C10—C11 | 120.90 (19) |
C3—C2—C1 | 116.09 (16) | C9—C10—H10 | 119.6 |
C2—C3—C4 | 113.82 (16) | C11—C10—H10 | 119.6 |
C2—C3—H3A | 108.8 | C10—C11—C6 | 119.99 (18) |
C4—C3—H3A | 108.8 | C10—C11—C1 | 117.91 (17) |
C2—C3—H3B | 108.8 | C6—C11—C1 | 122.07 (17) |
C4—C3—H3B | 108.8 | C2—C12—C13 | 130.51 (18) |
H3A—C3—H3B | 107.7 | C2—C12—H12 | 114.7 |
C3—C4—C5 | 111.98 (16) | C13—C12—H12 | 114.7 |
C3—C4—H4A | 109.2 | C18—C13—C14 | 117.39 (19) |
C5—C4—H4A | 109.2 | C18—C13—C12 | 117.75 (18) |
C3—C4—H4B | 109.2 | C14—C13—C12 | 124.81 (17) |
C5—C4—H4B | 109.2 | C15—C14—C13 | 120.99 (18) |
H4A—C4—H4B | 107.9 | C15—C14—H14 | 119.5 |
C6—C5—C4 | 112.27 (17) | C13—C14—H14 | 119.5 |
C6—C5—H5A | 109.1 | C16—C15—C14 | 119.82 (19) |
C4—C5—H5A | 109.1 | C16—C15—H15 | 120.1 |
C6—C5—H5B | 109.1 | C14—C15—H15 | 120.1 |
C4—C5—H5B | 109.1 | C17—C16—C15 | 120.9 (2) |
H5A—C5—H5B | 107.9 | C17—C16—Cl1 | 119.91 (16) |
C7—C6—C11 | 118.35 (19) | C15—C16—Cl1 | 119.19 (17) |
C7—C6—C5 | 120.36 (18) | C16—C17—C18 | 118.90 (19) |
C11—C6—C5 | 121.30 (18) | C16—C17—H17 | 120.6 |
C6—C7—C8 | 121.4 (2) | C18—C17—H17 | 120.6 |
C6—C7—H7 | 119.3 | C17—C18—C13 | 122.0 (2) |
C8—C7—H7 | 119.3 | C17—C18—H18 | 119.0 |
C9—C8—C7 | 119.8 (2) | C13—C18—H18 | 119.0 |
C9—C8—H8 | 120.1 | ||
O1—C1—C2—C12 | 14.6 (3) | C5—C6—C11—C1 | −3.0 (3) |
C11—C1—C2—C12 | −166.52 (17) | O1—C1—C11—C10 | 38.8 (3) |
O1—C1—C2—C3 | −163.47 (18) | C2—C1—C11—C10 | −140.10 (18) |
C11—C1—C2—C3 | 15.4 (2) | O1—C1—C11—C6 | −139.2 (2) |
C12—C2—C3—C4 | 101.3 (2) | C2—C1—C11—C6 | 42.0 (3) |
C1—C2—C3—C4 | −80.8 (2) | C3—C2—C12—C13 | −3.2 (3) |
C2—C3—C4—C5 | 39.8 (2) | C1—C2—C12—C13 | 178.97 (18) |
C3—C4—C5—C6 | 48.7 (2) | C2—C12—C13—C18 | 157.7 (2) |
C4—C5—C6—C7 | 108.5 (2) | C2—C12—C13—C14 | −24.7 (3) |
C4—C5—C6—C11 | −71.4 (2) | C18—C13—C14—C15 | −1.1 (3) |
C11—C6—C7—C8 | 1.0 (3) | C12—C13—C14—C15 | −178.65 (19) |
C5—C6—C7—C8 | −178.97 (19) | C13—C14—C15—C16 | 0.0 (3) |
C6—C7—C8—C9 | −0.3 (3) | C14—C15—C16—C17 | 0.5 (3) |
C7—C8—C9—C10 | −0.5 (3) | C14—C15—C16—Cl1 | 178.57 (16) |
C8—C9—C10—C11 | 0.7 (3) | C15—C16—C17—C18 | 0.1 (3) |
C9—C10—C11—C6 | 0.0 (3) | Cl1—C16—C17—C18 | −178.02 (16) |
C9—C10—C11—C1 | −177.98 (18) | C16—C17—C18—C13 | −1.2 (3) |
C7—C6—C11—C10 | −0.8 (3) | C14—C13—C18—C17 | 1.6 (3) |
C5—C6—C11—C10 | 179.14 (17) | C12—C13—C18—C17 | 179.39 (18) |
C7—C6—C11—C1 | 177.07 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···O1i | 0.95 | 2.50 | 3.319 (2) | 145 |
C3—H3A···Cg1ii | 0.99 | 2.83 | 3.572 (2) | 132 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2. |
C19H15NO | F(000) = 576 |
Mr = 273.32 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 12.4725 (4) Å | Cell parameters from 3885 reflections |
b = 7.1718 (2) Å | θ = 5.7–69.4° |
c = 15.9983 (5) Å | µ = 0.64 mm−1 |
β = 106.120 (3)° | T = 100 K |
V = 1374.79 (8) Å3 | Block, colourless |
Z = 4 | 0.17 × 0.10 × 0.03 mm |
XtaLAB AFC11 (RCD3): quarter-chi single CCD diffractometer | 2511 independent reflections |
Radiation source: Rotating-anode X-ray tube | 2302 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.059 |
ω scans | θmax = 68.2°, θmin = 3.7° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku, 2017) | h = −14→15 |
Tmin = 0.895, Tmax = 1.000 | k = −7→8 |
9732 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.068 | H-atom parameters constrained |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.1396P)2 + 0.1712P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2511 reflections | Δρmax = 0.49 e Å−3 |
190 parameters | Δρmin = −0.32 e Å−3 |
0 restraints |
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 | ||
C1 | 0.34825 (12) | 0.5911 (2) | 0.45058 (9) | 0.0284 (4) | |
C2 | 0.29525 (12) | 0.4044 (2) | 0.42080 (9) | 0.0275 (4) | |
C3 | 0.32674 (12) | 0.3153 (2) | 0.34549 (9) | 0.0279 (4) | |
H3A | 0.3150 | 0.1790 | 0.3474 | 0.033* | |
H3B | 0.4073 | 0.3366 | 0.3529 | 0.033* | |
C4 | 0.26091 (13) | 0.3882 (2) | 0.25527 (10) | 0.0292 (4) | |
H4A | 0.3080 | 0.3783 | 0.2148 | 0.035* | |
H4B | 0.1941 | 0.3093 | 0.2323 | 0.035* | |
C5 | 0.22444 (13) | 0.5911 (2) | 0.25887 (10) | 0.0296 (4) | |
H5A | 0.1850 | 0.6337 | 0.1994 | 0.036* | |
H5B | 0.1717 | 0.5993 | 0.2950 | 0.036* | |
C6 | 0.32277 (12) | 0.7168 (2) | 0.29642 (9) | 0.0279 (4) | |
C7 | 0.35894 (13) | 0.8371 (2) | 0.24193 (10) | 0.0304 (4) | |
H7 | 0.3192 | 0.8421 | 0.1820 | 0.037* | |
C8 | 0.45193 (14) | 0.9506 (2) | 0.27303 (11) | 0.0319 (4) | |
H8 | 0.4759 | 1.0306 | 0.2344 | 0.038* | |
C9 | 0.50973 (13) | 0.9462 (2) | 0.36109 (11) | 0.0318 (4) | |
H9 | 0.5734 | 1.0232 | 0.3829 | 0.038* | |
C10 | 0.47389 (13) | 0.8293 (2) | 0.41635 (10) | 0.0305 (4) | |
H10 | 0.5128 | 0.8279 | 0.4765 | 0.037* | |
C11 | 0.38136 (12) | 0.7129 (2) | 0.38553 (10) | 0.0279 (4) | |
C12 | 0.23202 (13) | 0.3273 (2) | 0.46664 (10) | 0.0294 (4) | |
H12 | 0.2248 | 0.3944 | 0.5160 | 0.035* | |
C13 | 0.17236 (13) | 0.1477 (2) | 0.44785 (10) | 0.0284 (4) | |
C14 | 0.11644 (13) | 0.0939 (2) | 0.36261 (10) | 0.0304 (4) | |
H14 | 0.1162 | 0.1752 | 0.3157 | 0.036* | |
C15 | 0.06168 (13) | −0.0752 (2) | 0.34565 (10) | 0.0304 (4) | |
H15 | 0.0252 | −0.1102 | 0.2874 | 0.036* | |
C16 | 0.05996 (12) | −0.1944 (2) | 0.41403 (10) | 0.0288 (4) | |
C17 | 0.11421 (14) | −0.1427 (2) | 0.49975 (10) | 0.0327 (4) | |
H17 | 0.1138 | −0.2237 | 0.5466 | 0.039* | |
C18 | 0.16847 (13) | 0.0273 (2) | 0.51552 (10) | 0.0320 (4) | |
H18 | 0.2040 | 0.0630 | 0.5738 | 0.038* | |
C19 | −0.00015 (13) | −0.3676 (2) | 0.39548 (10) | 0.0308 (4) | |
N1 | −0.05047 (12) | −0.5036 (2) | 0.37711 (9) | 0.0374 (4) | |
O1 | 0.36770 (11) | 0.63971 (17) | 0.52639 (7) | 0.0376 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0239 (8) | 0.0341 (9) | 0.0233 (8) | 0.0023 (6) | 0.0002 (6) | −0.0017 (6) |
C2 | 0.0235 (7) | 0.0299 (8) | 0.0234 (8) | 0.0018 (6) | −0.0028 (6) | 0.0020 (6) |
C3 | 0.0228 (7) | 0.0306 (8) | 0.0273 (8) | 0.0001 (6) | 0.0020 (6) | −0.0004 (6) |
C4 | 0.0263 (8) | 0.0345 (9) | 0.0243 (8) | −0.0036 (6) | 0.0030 (6) | −0.0032 (6) |
C5 | 0.0256 (8) | 0.0356 (9) | 0.0231 (8) | −0.0009 (6) | −0.0009 (6) | 0.0006 (6) |
C6 | 0.0248 (8) | 0.0304 (8) | 0.0264 (8) | 0.0042 (6) | 0.0034 (6) | −0.0011 (6) |
C7 | 0.0278 (8) | 0.0311 (8) | 0.0307 (9) | 0.0048 (6) | 0.0054 (7) | 0.0001 (6) |
C8 | 0.0314 (8) | 0.0286 (8) | 0.0375 (9) | 0.0031 (6) | 0.0122 (7) | 0.0008 (6) |
C9 | 0.0244 (8) | 0.0305 (8) | 0.0391 (9) | −0.0001 (6) | 0.0065 (7) | −0.0044 (7) |
C10 | 0.0254 (8) | 0.0307 (8) | 0.0317 (9) | 0.0019 (6) | 0.0016 (6) | −0.0038 (6) |
C11 | 0.0235 (7) | 0.0288 (8) | 0.0292 (8) | 0.0015 (6) | 0.0035 (6) | −0.0021 (6) |
C12 | 0.0272 (8) | 0.0323 (8) | 0.0243 (8) | 0.0018 (6) | −0.0002 (6) | −0.0001 (6) |
C13 | 0.0236 (8) | 0.0321 (9) | 0.0277 (8) | 0.0015 (6) | 0.0042 (6) | −0.0011 (6) |
C14 | 0.0274 (8) | 0.0340 (9) | 0.0257 (8) | −0.0011 (6) | 0.0009 (6) | 0.0060 (6) |
C15 | 0.0263 (8) | 0.0354 (9) | 0.0248 (8) | −0.0013 (6) | −0.0006 (6) | 0.0005 (6) |
C16 | 0.0239 (7) | 0.0300 (8) | 0.0294 (8) | 0.0004 (6) | 0.0025 (6) | 0.0006 (6) |
C17 | 0.0332 (8) | 0.0359 (9) | 0.0256 (8) | −0.0014 (7) | 0.0027 (7) | 0.0045 (6) |
C18 | 0.0312 (8) | 0.0371 (9) | 0.0245 (8) | −0.0022 (7) | 0.0024 (6) | −0.0005 (6) |
C19 | 0.0300 (8) | 0.0339 (9) | 0.0259 (8) | 0.0023 (7) | 0.0033 (6) | 0.0036 (6) |
N1 | 0.0377 (8) | 0.0359 (9) | 0.0338 (8) | −0.0053 (6) | 0.0018 (6) | 0.0021 (6) |
O1 | 0.0426 (7) | 0.0412 (7) | 0.0259 (6) | −0.0094 (5) | 0.0042 (5) | −0.0047 (5) |
C1—O1 | 1.2199 (19) | C8—H8 | 0.9500 |
C1—C11 | 1.502 (2) | C9—C10 | 1.380 (2) |
C1—C2 | 1.510 (2) | C9—H9 | 0.9500 |
C2—C12 | 1.337 (2) | C10—C11 | 1.399 (2) |
C2—C3 | 1.509 (2) | C10—H10 | 0.9500 |
C3—C4 | 1.540 (2) | C12—C13 | 1.476 (2) |
C3—H3A | 0.9900 | C12—H12 | 0.9500 |
C3—H3B | 0.9900 | C13—C18 | 1.396 (2) |
C4—C5 | 1.531 (2) | C13—C14 | 1.402 (2) |
C4—H4A | 0.9900 | C14—C15 | 1.381 (2) |
C4—H4B | 0.9900 | C14—H14 | 0.9500 |
C5—C6 | 1.506 (2) | C15—C16 | 1.393 (2) |
C5—H5A | 0.9900 | C15—H15 | 0.9500 |
C5—H5B | 0.9900 | C16—C17 | 1.400 (2) |
C6—C7 | 1.388 (2) | C16—C19 | 1.439 (2) |
C6—C11 | 1.410 (2) | C17—C18 | 1.383 (2) |
C7—C8 | 1.391 (2) | C17—H17 | 0.9500 |
C7—H7 | 0.9500 | C18—H18 | 0.9500 |
C8—C9 | 1.393 (2) | C19—N1 | 1.153 (2) |
O1—C1—C11 | 120.38 (14) | C9—C8—H8 | 120.2 |
O1—C1—C2 | 121.05 (14) | C10—C9—C8 | 119.53 (15) |
C11—C1—C2 | 118.52 (13) | C10—C9—H9 | 120.2 |
C12—C2—C3 | 125.92 (15) | C8—C9—H9 | 120.2 |
C12—C2—C1 | 117.85 (14) | C9—C10—C11 | 121.29 (14) |
C3—C2—C1 | 116.04 (13) | C9—C10—H10 | 119.4 |
C2—C3—C4 | 114.54 (13) | C11—C10—H10 | 119.4 |
C2—C3—H3A | 108.6 | C10—C11—C6 | 119.32 (14) |
C4—C3—H3A | 108.6 | C10—C11—C1 | 117.50 (14) |
C2—C3—H3B | 108.6 | C6—C11—C1 | 123.17 (14) |
C4—C3—H3B | 108.6 | C2—C12—C13 | 126.19 (14) |
H3A—C3—H3B | 107.6 | C2—C12—H12 | 116.9 |
C5—C4—C3 | 111.96 (12) | C13—C12—H12 | 116.9 |
C5—C4—H4A | 109.2 | C18—C13—C14 | 117.97 (14) |
C3—C4—H4A | 109.2 | C18—C13—C12 | 120.39 (14) |
C5—C4—H4B | 109.2 | C14—C13—C12 | 121.63 (14) |
C3—C4—H4B | 109.2 | C15—C14—C13 | 121.18 (14) |
H4A—C4—H4B | 107.9 | C15—C14—H14 | 119.4 |
C6—C5—C4 | 111.51 (12) | C13—C14—H14 | 119.4 |
C6—C5—H5A | 109.3 | C14—C15—C16 | 119.93 (14) |
C4—C5—H5A | 109.3 | C14—C15—H15 | 120.0 |
C6—C5—H5B | 109.3 | C16—C15—H15 | 120.0 |
C4—C5—H5B | 109.3 | C15—C16—C17 | 119.88 (15) |
H5A—C5—H5B | 108.0 | C15—C16—C19 | 119.24 (14) |
C7—C6—C11 | 118.67 (14) | C17—C16—C19 | 120.86 (14) |
C7—C6—C5 | 119.49 (13) | C18—C17—C16 | 119.40 (15) |
C11—C6—C5 | 121.83 (14) | C18—C17—H17 | 120.3 |
C6—C7—C8 | 121.55 (15) | C16—C17—H17 | 120.3 |
C6—C7—H7 | 119.2 | C17—C18—C13 | 121.62 (14) |
C8—C7—H7 | 119.2 | C17—C18—H18 | 119.2 |
C7—C8—C9 | 119.64 (15) | C13—C18—H18 | 119.2 |
C7—C8—H8 | 120.2 | N1—C19—C16 | 177.09 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···N1i | 0.95 | 2.54 | 3.438 (2) | 157 |
C3—H3A···Cg1ii | 0.99 | 2.84 | 3.6730 (16) | 142 |
C8—H8···Cg1iii | 0.95 | 2.88 | 3.7868 (17) | 161 |
Symmetry codes: (i) −x, −y−1, −z+1; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1/2. |
Contact type | (I) | VENQUA |
H···H | 54.8 | 55.3 |
C···H/H···C | 28.1 | 29.2 |
O—H/H···O | 15.3 | 14.5 |
C···C | 1.1 | 0.0 |
C···O/O···C | 0.8 | 0.8 |
O···O | 0.0 | 0.2 |
Code/refcode | Substituent(s) | Space group | φ | Donor atom(s) | Packing motif |
(I) | 4-OMe | P21/c | 23.79 (3) | C15 | C(8) chain |
(II) | 4-OEt | P21/c | 24.60 (4) | C18 | R22(14) loop |
(III) | 4-OBz | P1 | 33.72 (4) | C15 | C(8) chain |
(IV) | 4-Cl | P21/n | 29.93 (8) | C10 | R22(10) loop |
(V) | 4-CN | P21/c | 21.81 (7) | C17 | R22(10) loop |
VENQOU | 4-Me | P21/n | 29.72 (11) | C10 | R22(10) loop |
VENQUA | 4-OMe | P21/n | 35.88 (11) | C10 | R22(10) loop |
VENSIQ | 4-NMe2 | P21/n | 29.43 (11) | C10 | R22(10) loop |
XUGXOM | 2-NO2 | P21/a | 27.56 (6) | C17 | C(5) chain |
VENREL | 3-NO2 | P1 | 18.54 (9) | C7,C14,C16 | double chain |
VENRIP | 4-NO2 | P1 | 45.32 (9) | C9,C15 | sheet |
XUGYED | 2-Cl | P21/c | 28.40 (19) | C14 | C(7) chain |
XUGXUS | 3,4-Cl | P21/c | 39.01 (16) | C15 | C(8) chain |
XUGYAZ | 2,4-Cl | P21/c | 30.54 (12) | C14 | C(7) chain |
XUGYUT | 2-OMe | P21 | 25.82 (17) | None | – |
XUGYON | 3,4-OMe | P1 | 23.48 (9) | C8,C15 | sheet |
XUGYIH | 3,4,5-OMe | P21/n | 35.08 (10) | C7 | C(6) chain |
Packing analyses carried out using PLATON (Spek, 2009); φ is the dihedral angle between the C6–C11 and C13–C18 benzene rings; for the `VEN' refcode family, see Dimmock et al. (1999); for the `XUG' family, see Dimmock et al. (2002); the donor atom labels correspond to our atom numbering scheme. |
Acknowledgements
We thank the EPSRC National Crystallography Service (University of Southampton) for the X-ray data collections and Edward Tiekink for assistance with the overlay plot.
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