research communications
The crystal structures of two E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one
(2aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
In the crystal of compound (I), C14H11ClOS, molecules are linked by C—H⋯O hydrogen bonds to form simple C(5) chains. Compound (II), C26H22O, crystallizes with Z′ = 2 in P-1; one of the molecules is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.644 (3) and 0.356 (3). The two disordered components differ from one another in the orientation of the isopropyl substituents, and both differ from the ordered molecules in the arrangement of the central propenone spacer unit, so that the crystal of (II) contains three distinct conformers. The ordered and disordered conformers each form a C(8) chain built from a single type of C—H⋯O hydrogen bond but those formed by the disordered conformers differ from that formed by the ordered form.
1. Chemical context
R1—C(=O)—CH=CH—R2, are versatile intermediates in synthesis (Baktır et al., 2011; Samshuddin et al., 2011, 2012, 2014; Nayak et al., 2014; Salian et al., 2015; Mohan et al., 2016). Compounds of this class also exhibit a wide range of biological activity, including anti-bacterial (Tran et al., 2012), anti-cancer (Syam et al., 2012; Kumar et al., 2014), anti-fungal (López et al., 2001), anti-inflammatory (Fang et al., 2015), anti-malarial (Agarwal et al., 2005) and antitubercular activities (Dimmock et al., 1999). Accordingly, the synthesis and characterization of new examples of this type is of interest and potentially of value and herein we report on the synthesis and crystal structures of two further examples; (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)-prop-2-en-1-one (I), and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one (II). Compounds (I) and (II) were prepared by base-induced condensation of an aryl aldehyde, 2-methylbenzaldehyde in the case of (I) or 4-isopropylbenzaldehyde for (II) with, respectively, 2-acetyl-5-chlorothiophene or 9-acetylanthracene.
2. Structural commentary
In the molecule of compound (I), Fig. 1, the central spacer unit comprising the atoms (C12,C1,C2,C3,C31) is effectively planar: the maximum deviation from the mean plane of these atoms is 0.21 (2) Å, with an r.m.s. deviation of 0.025 Å. The heterocyclic ring is nearly co-planar with the spacer unit, making with it a dihedral angle of 1.41 (1)°. The dihedral angles between the phenyl group and the spacer unit, and between the two rings are 10.95 (11) and 9.81 (10)°, respectively. The bond distances within the molecule of (I) show clearly the localized double bond between atoms C2 and C3, and the distances within the thiophene ring clearly rule out the possibility of any orientational disorder of the type sometimes found in thiophene rings (Cobo et al., 2005; Trilleras et al., 2005, 2009; Insuasty et al., 2014).
Compound (II) crystallizes with Z′ = 2 in P. The molecule containing atom O11 (Fig. 2) is fully ordered, but the other molecule is disordered over two sets of atomic sites: the major-disorder component containing atom O21 (Fig. 3) has occupancy 0.644 (3) while the minor-disorder component containing atom O31 (Fig. 4) has occupancy 0.356 (3). All three forms exhibit different conformations, as discussed below, and it will be convenient to refer to the molecules containing atoms O11, O21 or O31 as conformers of types 1, 2 or 3, respectively.
In the fully ordered molecule containing atom O11 the torsional angle C119—C11—C12—C13 is 177.72 (16)° whereas in the two disordered components containing atoms O21 and O31 the values of the corresponding torsional angles Cn19—Cn1—Cn2—Cn3 are 11 (3)° and 12 (5)° for n = 2 and 3 respectively, corresponding to a rotation of approximately 180° about the bond Cn1—Cn2 in conformers 2 and 3 as compared with conformer 1. In addition, in conformers 2 and 3 the torsional angles Cn33—Cn34—Cn37—Hn37 are −14° and −170° for n = 2 and 3, respectively, so that the orientation of the CHMe2 group in these two forms differs by a rotation of approximately 180° about the bond Cn34—Cn37; the corresponding value in conformer 1 is ca 162°. Hence three different conformations of compound (II) co-exist in the same crystal (cf. Figs. 2–4) with relative abundances 1.000:0.644 (3):0.356 (3) in the crystal selected for data collection. Conformer 1 thus differs from conformers 2 and 3 in the arrangement of the central spacer unit, while conformers 1 and 3 exhibit similar orientations of the isopropyl unit relative to the adjacent phenyl ring, but different from that in conformer 2.
In each conformer, the central spacer unit encompassing atoms Cn19,Cn1,Cn2,Cn3,Cn31 is effectively planar with r.m.s. deviations from the mean planes of 0.011, 0.036 and 0.043 Å for n = 1–3, respectively. This spacer unit makes dihedral angles with the central ring of the anthracene unit of 67.70 (11), 65.7 (5) and 71.7 (10)° for n = 1–3, respectively, and the corresponding dihedral angles with the adjacent aryl rings Cn31—Cn36 are 6.26 (18), 1.5 (11) and 7(2)°, respectively. These values confirm that the principal difference between conformer 1 and conformers 2 and 3 is simply a rotation about the bond Cn1—Cn2.
Within each of the anthracene units, the distances Cn11—Cn12, Cn13—Cn14, Cn15—Cn16 and Cn17—Cn18 are very much shorter than the other C—C bonds in these units, while the C—C distances in the central rings show rather little variation. These observations are consistent with an electronic structure for the anthracene units where a central ring displaying aromatic delocalization is flanked by two isolated diene units (Glidewell & Lloyd, 1984,1986).
3. Supramolecular features
In the crystal of compound (I), molecule related by a c-glide plane are linked by a single C—H⋯O hydrogen bond (Table 1) to form a C(5) chain running parallel to the [001] direction (Fig. 5). In the crystal of compound (II), molecules are also linked into chains by C—H⋯O hydrogen bonds (Table 2), but the chains formed by the ordered and disordered forms are different, in that in the chain of ordered molecules the donor is a phenyl C—H unit, while in the disordered forms the donors are part of the anthracene units. In both types of chain molecules related by translation form C(8) chains running parallel to the [100] direction (Fig. 6). In addition, inversion-related pairs of the chains built from the disordered components are weakly linked by C—H⋯π interactions (Table 2).
4. Database survey
The structures of a number of have been reported recently (Naik, Shettigar et al., 2015; Naik, Yathirajan et al., 2015). There are no hydrogen bonds of any kind in the crystals of the isostructural compounds (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one and (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one, but in the isostructural compounds (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one and (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one the molecules are linked by C—H⋯O hydrogen bonds to form simple C(7) chains, while C(5) chains are present in the structure of (2E)-1-(5-bromothiophen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one. In the structure of (2E, 2'E)-3, 3′-(1,3-phenylene)-bis(1-(anthracene-9-yl)prop-2-en-1-one), which is related to compound (II), inversion-related pairs of molecules are linked by multiple C—H⋯O hydrogen bonds to form centrosymmetric dimers (Kant et al., 2015). In the recently reported structure of (2E)-3-(2,4-dichlorophenyl)-1-(2-methoxyphenyl)prop-2-en-1-one (Salian et al., 2016), there are no hydrogen bonds of any kind, but the molecules are linked into chains by π–π stacking interactions.
containing substituted thiophene units, and thus closely related to compound (I)5. Synthesis and crystallization
For the synthesis of compound (I), a solution of 2-methylbenzaldehyde (0.075 g, 0.625 mol) in methanol (20 ml) was added to solution of with 2-acetyl-5-chlorothiophene (0.100 g, 0.625 mol) in methanol (10 ml) and to this mixture was added aqueous sodium hydroxide solution (40% w/v, 5 ml). The reaction mixture was then stirred at 301 K for 4 h, when the resulting solid product was collected by filtration, washed with cold water and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature, of a solution in acetone-dimethylformamide (1:1, v/v): m. p. 387–389 K. For the synthesis of compound (II), aqueous sodium hydroxide solution (10%, w/v, 15 ml) was added to a mixture of 4-isopropylbenzaldehyde (1.5 ml, 0.01 mol) and 9-acetylanthracene (2.2 g, 0.01 mol) in ethanol (50 ml), and the resulting mixture was stirred at 278 K for 3 h. The resulting solid product was collected by filtration and recrystallized from ethanol solution: m.p. 369–371 K. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature, of a solution in dimethylformamide.
6. Refinement
Crystal data, data collection and structure . It was obvious from an early stage in the of compound (II) that one of the two independent molecules was disordered over two sets of atomic sites having unequal occupancies. For the minor-disorder component the bonded distances and the one-angle non-bonded distances were restrained to be the same as the corresponding distances in the major component, subject to s.u.s of 0.005 and 0.01 Å respectively. In addition, the anisotropic displacement parameters for corresponding atomic pairs of atomic sites in the two disorder components were constrained to be identical and, subject to these conditions the occupancies for the two components refined to values of 0.645 (4) and 0.355 (4). The H atoms in all but the minor-disorder component of compound (II) were located in difference maps and then treated as riding atoms in geometrically idealized positions with C—H distances 0.93 Å (alkenyl, aromatic and heteroaromatic), 0.96 Å (methyl) or 0.98 Å (aliphatic C—H) and with Uiso(H) = kUeq(C) where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other H atoms. The H atoms in the minor-disorder component were included in the in calculated positions under exactly the same conditions. For compound (II), 16 bad outliers of low intensity were omitted from the final refinements. In the final analysis of variance for compound (I) there was a fairly large value, 2.583, of K = mean (Fo2)/mean (Fc2) for the group of 287 very weak reflections having Fc/Fc(max) in the range 0.000 < Fc/Fc(max) < 0.006. For compound (II), there was a large value of K, 10.808, for the group of 733 very weak reflections having Fc/Fc(max) in the range 0.000 < Fc/Fc(max) < 0.005.
details are summarized in Table 3
|
Supporting information
https://doi.org/10.1107/S2056989016011592/su5313sup1.cif
contains datablocks global, I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016011592/su5313Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989016011592/su5313IIsup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989016011592/su5313Isup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989016011592/su5313IIsup5.cml
For both compounds, data collection: CrysAlis PRO (Agilent, 2014); cell
CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C14H11ClOS | F(000) = 544 |
Mr = 262.74 | Dx = 1.391 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.7179 (7) Å | Cell parameters from 2913 reflections |
b = 7.5783 (4) Å | θ = 3.0–29.4° |
c = 11.5451 (5) Å | µ = 0.45 mm−1 |
β = 102.999 (4)° | T = 298 K |
V = 1254.70 (11) Å3 | Block, colourless |
Z = 4 | 0.26 × 0.22 × 0.15 mm |
Agilent Xcalibur Eos Gemini diffractometer | 2053 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.028 |
φ and ω scans | θmax = 27.6°, θmin = 3.0° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −17→18 |
Tmin = 0.832, Tmax = 0.935 | k = −5→9 |
6097 measured reflections | l = −14→14 |
2785 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0304P)2 + 0.3588P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.18 e Å−3 |
2785 reflections | Δρmin = −0.19 e Å−3 |
156 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0028 (8) |
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 | 0.43382 (14) | 0.2903 (3) | 0.56191 (17) | 0.0443 (5) | |
O1 | 0.41785 (10) | 0.3013 (2) | 0.66164 (12) | 0.0649 (5) | |
C2 | 0.36322 (13) | 0.3328 (3) | 0.45350 (17) | 0.0451 (5) | |
H2 | 0.3771 | 0.3155 | 0.3796 | 0.054* | |
C3 | 0.28068 (14) | 0.3950 (3) | 0.45918 (17) | 0.0458 (5) | |
H3 | 0.2706 | 0.4129 | 0.5350 | 0.055* | |
S11 | 0.60913 (4) | 0.18403 (8) | 0.67339 (4) | 0.04994 (18) | |
C12 | 0.52502 (13) | 0.2307 (3) | 0.54715 (16) | 0.0398 (5) | |
C13 | 0.55665 (13) | 0.1979 (3) | 0.44730 (16) | 0.0441 (5) | |
H13 | 0.5207 | 0.2148 | 0.3709 | 0.053* | |
C14 | 0.64871 (14) | 0.1362 (3) | 0.47103 (17) | 0.0485 (5) | |
H14 | 0.6808 | 0.1076 | 0.4128 | 0.058* | |
C15 | 0.68504 (13) | 0.1233 (3) | 0.58937 (17) | 0.0434 (5) | |
Cl15 | 0.79457 (4) | 0.05248 (8) | 0.65700 (5) | 0.0609 (2) | |
C31 | 0.20305 (13) | 0.4390 (3) | 0.35977 (16) | 0.0418 (5) | |
C32 | 0.12392 (14) | 0.5248 (3) | 0.38106 (19) | 0.0474 (5) | |
C33 | 0.05096 (15) | 0.5622 (3) | 0.2844 (2) | 0.0569 (6) | |
H33 | −0.0020 | 0.6185 | 0.2974 | 0.068* | |
C34 | 0.05518 (16) | 0.5185 (3) | 0.1710 (2) | 0.0623 (7) | |
H34 | 0.0054 | 0.5449 | 0.1081 | 0.075* | |
C35 | 0.13302 (15) | 0.4352 (3) | 0.14948 (19) | 0.0588 (6) | |
H35 | 0.1362 | 0.4061 | 0.0722 | 0.071* | |
C36 | 0.20586 (14) | 0.3957 (3) | 0.24326 (17) | 0.0499 (5) | |
H36 | 0.2582 | 0.3388 | 0.2287 | 0.060* | |
C37 | 0.11721 (16) | 0.5819 (4) | 0.5038 (2) | 0.0667 (7) | |
H37A | 0.1232 | 0.4808 | 0.5550 | 0.100* | |
H37B | 0.0579 | 0.6372 | 0.4999 | 0.100* | |
H37C | 0.1662 | 0.6643 | 0.5347 | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0463 (11) | 0.0518 (13) | 0.0340 (10) | −0.0035 (10) | 0.0071 (8) | −0.0033 (9) |
O1 | 0.0549 (9) | 0.1060 (14) | 0.0336 (8) | 0.0117 (9) | 0.0097 (6) | −0.0032 (8) |
C2 | 0.0449 (11) | 0.0563 (13) | 0.0330 (10) | −0.0021 (10) | 0.0063 (8) | −0.0011 (9) |
C3 | 0.0497 (12) | 0.0521 (13) | 0.0365 (10) | 0.0002 (10) | 0.0113 (8) | −0.0001 (9) |
S11 | 0.0493 (3) | 0.0704 (4) | 0.0272 (2) | 0.0019 (3) | 0.0024 (2) | −0.0003 (2) |
C12 | 0.0404 (10) | 0.0463 (12) | 0.0304 (9) | −0.0043 (9) | 0.0031 (7) | 0.0003 (8) |
C13 | 0.0439 (11) | 0.0570 (13) | 0.0293 (9) | −0.0010 (10) | 0.0039 (8) | 0.0033 (9) |
C14 | 0.0465 (11) | 0.0648 (14) | 0.0350 (10) | 0.0018 (11) | 0.0107 (8) | 0.0006 (10) |
C15 | 0.0406 (10) | 0.0469 (12) | 0.0405 (11) | −0.0031 (10) | 0.0042 (8) | 0.0019 (9) |
Cl15 | 0.0479 (3) | 0.0704 (4) | 0.0579 (4) | 0.0077 (3) | −0.0016 (2) | 0.0077 (3) |
C31 | 0.0420 (11) | 0.0417 (11) | 0.0407 (11) | −0.0055 (9) | 0.0074 (8) | 0.0037 (9) |
C32 | 0.0450 (11) | 0.0456 (12) | 0.0523 (12) | −0.0067 (10) | 0.0124 (9) | 0.0000 (10) |
C33 | 0.0407 (11) | 0.0606 (15) | 0.0679 (15) | 0.0019 (11) | 0.0090 (10) | 0.0045 (12) |
C34 | 0.0505 (13) | 0.0740 (17) | 0.0557 (14) | −0.0022 (13) | −0.0021 (10) | 0.0132 (13) |
C35 | 0.0564 (13) | 0.0760 (17) | 0.0413 (12) | −0.0036 (13) | 0.0048 (9) | 0.0076 (11) |
C36 | 0.0469 (11) | 0.0598 (14) | 0.0425 (11) | 0.0013 (11) | 0.0090 (9) | 0.0039 (10) |
C37 | 0.0559 (14) | 0.0811 (19) | 0.0661 (16) | 0.0043 (13) | 0.0199 (11) | −0.0140 (14) |
C1—O1 | 1.229 (2) | C31—C36 | 1.394 (3) |
C1—C12 | 1.462 (3) | C31—C32 | 1.403 (3) |
C1—C2 | 1.471 (3) | C32—C33 | 1.393 (3) |
C2—C3 | 1.318 (3) | C32—C37 | 1.506 (3) |
C2—H2 | 0.9300 | C33—C34 | 1.365 (3) |
C3—C31 | 1.464 (3) | C33—H33 | 0.9300 |
C3—H3 | 0.9300 | C34—C35 | 1.379 (3) |
S11—C15 | 1.700 (2) | C34—H34 | 0.9300 |
S11—C12 | 1.7234 (18) | C35—C36 | 1.375 (3) |
C12—C13 | 1.360 (3) | C35—H35 | 0.9300 |
C13—C14 | 1.401 (3) | C36—H36 | 0.9300 |
C13—H13 | 0.9300 | C37—H37A | 0.9600 |
C14—C15 | 1.354 (3) | C37—H37B | 0.9600 |
C14—H14 | 0.9300 | C37—H37C | 0.9600 |
C15—Cl15 | 1.7118 (19) | ||
O1—C1—C12 | 120.29 (17) | C36—C31—C3 | 121.03 (18) |
O1—C1—C2 | 122.34 (18) | C32—C31—C3 | 120.03 (18) |
C12—C1—C2 | 117.37 (17) | C33—C32—C31 | 118.3 (2) |
C3—C2—C1 | 121.22 (18) | C33—C32—C37 | 119.6 (2) |
C3—C2—H2 | 119.4 | C31—C32—C37 | 122.06 (18) |
C1—C2—H2 | 119.4 | C34—C33—C32 | 121.7 (2) |
C2—C3—C31 | 127.43 (18) | C34—C33—H33 | 119.1 |
C2—C3—H3 | 116.3 | C32—C33—H33 | 119.1 |
C31—C3—H3 | 116.3 | C33—C34—C35 | 120.2 (2) |
C15—S11—C12 | 90.70 (9) | C33—C34—H34 | 119.9 |
C13—C12—C1 | 130.82 (17) | C35—C34—H34 | 119.9 |
C13—C12—S11 | 111.20 (14) | C36—C35—C34 | 119.4 (2) |
C1—C12—S11 | 117.94 (14) | C36—C35—H35 | 120.3 |
C12—C13—C14 | 113.31 (17) | C34—C35—H35 | 120.3 |
C12—C13—H13 | 123.3 | C35—C36—C31 | 121.4 (2) |
C14—C13—H13 | 123.3 | C35—C36—H36 | 119.3 |
C15—C14—C13 | 111.50 (18) | C31—C36—H36 | 119.3 |
C15—C14—H14 | 124.3 | C32—C37—H37A | 109.5 |
C13—C14—H14 | 124.3 | C32—C37—H37B | 109.5 |
C14—C15—S11 | 113.28 (15) | H37A—C37—H37B | 109.5 |
C14—C15—Cl15 | 126.91 (17) | C32—C37—H37C | 109.5 |
S11—C15—Cl15 | 119.81 (11) | H37A—C37—H37C | 109.5 |
C36—C31—C32 | 118.95 (18) | H37B—C37—H37C | 109.5 |
O1—C1—C2—C3 | 4.0 (3) | C12—S11—C15—Cl15 | −179.75 (14) |
C12—C1—C2—C3 | −176.9 (2) | C2—C3—C31—C36 | 8.6 (3) |
C1—C2—C3—C31 | −178.39 (19) | C2—C3—C31—C32 | −171.9 (2) |
O1—C1—C12—C13 | 175.4 (2) | C36—C31—C32—C33 | 0.4 (3) |
C2—C1—C12—C13 | −3.7 (3) | C3—C31—C32—C33 | −179.11 (19) |
O1—C1—C12—S11 | −2.0 (3) | C36—C31—C32—C37 | −177.6 (2) |
C2—C1—C12—S11 | 178.92 (15) | C3—C31—C32—C37 | 2.8 (3) |
C15—S11—C12—C13 | 0.45 (17) | C31—C32—C33—C34 | −0.4 (3) |
C15—S11—C12—C1 | 178.33 (17) | C37—C32—C33—C34 | 177.7 (2) |
C1—C12—C13—C14 | −177.9 (2) | C32—C33—C34—C35 | −0.1 (4) |
S11—C12—C13—C14 | −0.4 (2) | C33—C34—C35—C36 | 0.5 (4) |
C12—C13—C14—C15 | 0.1 (3) | C34—C35—C36—C31 | −0.4 (4) |
C13—C14—C15—S11 | 0.3 (3) | C32—C31—C36—C35 | 0.0 (3) |
C13—C14—C15—Cl15 | 179.56 (17) | C3—C31—C36—C35 | 179.5 (2) |
C12—S11—C15—C14 | −0.43 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O1i | 0.93 | 2.55 | 3.467 (2) | 169 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
C26H22O | Z = 4 |
Mr = 350.44 | F(000) = 744 |
Triclinic, P1 | Dx = 1.195 Mg m−3 |
a = 9.0150 (4) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 14.0601 (6) Å | Cell parameters from 7095 reflections |
c = 16.2611 (8) Å | θ = 3.5–68.0° |
α = 105.146 (4)° | µ = 0.55 mm−1 |
β = 95.967 (4)° | T = 296 K |
γ = 98.057 (4)° | Block, colourless |
V = 1948.46 (16) Å3 | 0.21 × 0.14 × 0.10 mm |
Agilent Xcalibur Eos Gemini diffractometer | 5485 reflections with I > 2σ(I) |
Detector resolution: 16.0416 pixels mm-1 | Rint = 0.035 |
φ and ω scans | θmax = 68.0°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −10→10 |
Tmin = 0.737, Tmax = 0.947 | k = −16→15 |
12946 measured reflections | l = −19→17 |
7079 independent reflections |
Refinement on F2 | 72 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0689P)2 + 0.2921P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
7079 reflections | Δρmax = 0.22 e Å−3 |
575 parameters | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C11 | 0.71500 (19) | 0.10252 (14) | 0.34353 (11) | 0.0392 (4) | |
O11 | 0.80294 (15) | 0.04914 (12) | 0.31426 (9) | 0.0570 (4) | |
C12 | 0.55261 (18) | 0.08287 (13) | 0.30901 (11) | 0.0390 (4) | |
H12 | 0.4899 | 0.1246 | 0.3359 | 0.047* | |
C13 | 0.49356 (18) | 0.00672 (13) | 0.24008 (10) | 0.0366 (4) | |
H13 | 0.5608 | −0.0324 | 0.2149 | 0.044* | |
C111 | 0.8247 (3) | 0.08400 (15) | 0.51371 (13) | 0.0549 (5) | |
H111 | 0.7926 | 0.0267 | 0.4678 | 0.066* | |
C112 | 0.8752 (3) | 0.07482 (18) | 0.59246 (15) | 0.0702 (7) | |
H112 | 0.8780 | 0.0116 | 0.5997 | 0.084* | |
C113 | 0.9235 (3) | 0.16040 (19) | 0.66349 (14) | 0.0706 (7) | |
H113 | 0.9579 | 0.1533 | 0.7171 | 0.085* | |
C114 | 0.9198 (2) | 0.25229 (17) | 0.65374 (12) | 0.0554 (5) | |
H114 | 0.9512 | 0.3079 | 0.7012 | 0.066* | |
C115 | 0.8165 (2) | 0.47150 (15) | 0.47098 (14) | 0.0509 (5) | |
H115 | 0.8472 | 0.5275 | 0.5182 | 0.061* | |
C116 | 0.7706 (2) | 0.48406 (17) | 0.39327 (16) | 0.0591 (5) | |
H116 | 0.7697 | 0.5481 | 0.3876 | 0.071* | |
C117 | 0.7240 (2) | 0.39997 (17) | 0.32061 (14) | 0.0534 (5) | |
H117 | 0.6926 | 0.4091 | 0.2673 | 0.064* | |
C118 | 0.72458 (19) | 0.30582 (15) | 0.32776 (12) | 0.0434 (4) | |
H118 | 0.6952 | 0.2515 | 0.2790 | 0.052* | |
C119 | 0.76971 (17) | 0.19321 (13) | 0.41974 (10) | 0.0350 (3) | |
C120 | 0.86656 (18) | 0.36079 (13) | 0.56169 (11) | 0.0413 (4) | |
H120 | 0.8978 | 0.4166 | 0.6091 | 0.050* | |
C121 | 0.81986 (19) | 0.17963 (13) | 0.49995 (11) | 0.0397 (4) | |
C122 | 0.86911 (19) | 0.26655 (14) | 0.57270 (11) | 0.0406 (4) | |
C123 | 0.81887 (17) | 0.37492 (13) | 0.48214 (11) | 0.0388 (4) | |
C124 | 0.76959 (16) | 0.28911 (13) | 0.40878 (10) | 0.0354 (4) | |
C131 | 0.33555 (18) | −0.02239 (12) | 0.19949 (10) | 0.0334 (3) | |
C132 | 0.22085 (19) | 0.02522 (13) | 0.23310 (11) | 0.0388 (4) | |
H132 | 0.2444 | 0.0772 | 0.2839 | 0.047* | |
C133 | 0.07321 (19) | −0.00304 (14) | 0.19272 (11) | 0.0415 (4) | |
H133 | −0.0010 | 0.0301 | 0.2168 | 0.050* | |
C134 | 0.03292 (18) | −0.08023 (12) | 0.11669 (10) | 0.0346 (3) | |
C135 | 0.14636 (19) | −0.12848 (13) | 0.08311 (10) | 0.0379 (4) | |
H135 | 0.1222 | −0.1806 | 0.0325 | 0.045* | |
C136 | 0.29520 (19) | −0.10051 (13) | 0.12369 (10) | 0.0384 (4) | |
H136 | 0.3691 | −0.1343 | 0.1000 | 0.046* | |
C137 | −0.12965 (19) | −0.11137 (14) | 0.07197 (11) | 0.0418 (4) | |
H137 | −0.1283 | −0.1496 | 0.0124 | 0.050* | |
C138 | −0.2217 (2) | −0.17970 (16) | 0.11443 (17) | 0.0579 (5) | |
H18A | −0.1753 | −0.2374 | 0.1131 | 0.087* | |
H18B | −0.3229 | −0.2006 | 0.0838 | 0.087* | |
H18C | −0.2247 | −0.1441 | 0.1731 | 0.087* | |
C139 | −0.2078 (2) | −0.02305 (17) | 0.06944 (15) | 0.0592 (6) | |
H19A | −0.2207 | 0.0115 | 0.1268 | 0.089* | |
H19B | −0.3050 | −0.0466 | 0.0342 | 0.089* | |
H19C | −0.1469 | 0.0218 | 0.0457 | 0.089* | |
C21 | 0.9228 (7) | 0.7212 (7) | 0.8184 (4) | 0.0348 (4) | 0.644 (3) |
O21 | 1.039 (2) | 0.767 (3) | 0.8666 (11) | 0.0455 (13) | 0.644 (3) |
C22 | 0.8944 (14) | 0.7333 (14) | 0.7316 (7) | 0.0352 (12) | 0.644 (3) |
H22 | 0.9723 | 0.7693 | 0.7131 | 0.042* | 0.644 (3) |
C23 | 0.7644 (14) | 0.6963 (12) | 0.6766 (6) | 0.0345 (14) | 0.644 (3) |
H23 | 0.6905 | 0.6548 | 0.6930 | 0.041* | 0.644 (3) |
C211 | 1.0065 (10) | 0.5367 (9) | 0.8411 (12) | 0.0385 (13) | 0.644 (3) |
H211 | 1.0698 | 0.5772 | 0.8175 | 0.046* | 0.644 (3) |
C212 | 1.0495 (10) | 0.4529 (8) | 0.8551 (10) | 0.0470 (11) | 0.644 (3) |
H212 | 1.1438 | 0.4383 | 0.8434 | 0.056* | 0.644 (3) |
C213 | 0.9526 (6) | 0.3874 (6) | 0.8874 (8) | 0.0501 (13) | 0.644 (3) |
H213 | 0.9858 | 0.3322 | 0.8996 | 0.060* | 0.644 (3) |
C214 | 0.8124 (7) | 0.4050 (6) | 0.9006 (9) | 0.0455 (12) | 0.644 (3) |
H214 | 0.7470 | 0.3587 | 0.9173 | 0.055* | 0.644 (3) |
C215 | 0.4326 (8) | 0.6279 (5) | 0.9197 (7) | 0.0391 (10) | 0.644 (3) |
H215 | 0.3670 | 0.5831 | 0.9380 | 0.047* | 0.644 (3) |
C216 | 0.3911 (8) | 0.7152 (4) | 0.9141 (7) | 0.0413 (12) | 0.644 (3) |
H216 | 0.2972 | 0.7292 | 0.9275 | 0.050* | 0.644 (3) |
C217 | 0.4909 (10) | 0.7852 (5) | 0.8880 (9) | 0.0407 (10) | 0.644 (3) |
H217 | 0.4633 | 0.8461 | 0.8862 | 0.049* | 0.644 (3) |
C218 | 0.6263 (12) | 0.7646 (6) | 0.8655 (13) | 0.0365 (10) | 0.644 (3) |
H218 | 0.6882 | 0.8104 | 0.8463 | 0.044* | 0.644 (3) |
C219 | 0.8136 (8) | 0.6487 (6) | 0.8467 (7) | 0.0312 (9) | 0.644 (3) |
C220 | 0.6222 (7) | 0.5163 (5) | 0.9079 (7) | 0.0375 (9) | 0.644 (3) |
H220 | 0.5581 | 0.4720 | 0.9275 | 0.045* | 0.644 (3) |
C221 | 0.8648 (10) | 0.5636 (9) | 0.8621 (13) | 0.0327 (11) | 0.644 (3) |
C222 | 0.7624 (10) | 0.4933 (8) | 0.8892 (12) | 0.0366 (8) | 0.644 (3) |
C223 | 0.5748 (10) | 0.6032 (6) | 0.8982 (10) | 0.0339 (8) | 0.644 (3) |
C224 | 0.6750 (13) | 0.6737 (9) | 0.8708 (15) | 0.0322 (6) | 0.644 (3) |
C231 | 0.7290 (9) | 0.7158 (7) | 0.5930 (4) | 0.0336 (11) | 0.644 (3) |
C232 | 0.8287 (5) | 0.7781 (5) | 0.5618 (3) | 0.0379 (7) | 0.644 (3) |
H232 | 0.9225 | 0.8087 | 0.5942 | 0.046* | 0.644 (3) |
C233 | 0.7891 (4) | 0.7948 (3) | 0.4830 (2) | 0.0399 (7) | 0.644 (3) |
H233 | 0.8569 | 0.8372 | 0.4636 | 0.048* | 0.644 (3) |
C234 | 0.6504 (4) | 0.7499 (3) | 0.43184 (18) | 0.0400 (7) | 0.644 (3) |
C235 | 0.5513 (4) | 0.6873 (3) | 0.4631 (2) | 0.0434 (8) | 0.644 (3) |
H235 | 0.4581 | 0.6559 | 0.4303 | 0.052* | 0.644 (3) |
C236 | 0.5898 (4) | 0.6713 (3) | 0.5423 (2) | 0.0393 (8) | 0.644 (3) |
H236 | 0.5212 | 0.6298 | 0.5622 | 0.047* | 0.644 (3) |
C237 | 0.6140 (3) | 0.7666 (3) | 0.34365 (19) | 0.0523 (7) | 0.644 (3) |
H237 | 0.6886 | 0.8228 | 0.3403 | 0.063* | 0.644 (3) |
C238 | 0.630 (3) | 0.6736 (15) | 0.2717 (5) | 0.0767 (12) | 0.644 (3) |
H28A | 0.6142 | 0.6872 | 0.2169 | 0.115* | 0.644 (3) |
H28B | 0.5550 | 0.6179 | 0.2722 | 0.115* | 0.644 (3) |
H28C | 0.7289 | 0.6578 | 0.2813 | 0.115* | 0.644 (3) |
C239 | 0.4590 (6) | 0.7932 (5) | 0.3291 (4) | 0.105 (2) | 0.644 (3) |
H29A | 0.4493 | 0.8494 | 0.3754 | 0.158* | 0.644 (3) |
H29B | 0.3832 | 0.7371 | 0.3270 | 0.158* | 0.644 (3) |
H29C | 0.4460 | 0.8101 | 0.2756 | 0.158* | 0.644 (3) |
C31 | 0.9247 (13) | 0.7242 (12) | 0.8178 (7) | 0.0348 (4) | 0.356 (3) |
O31 | 1.047 (4) | 0.767 (5) | 0.861 (2) | 0.0455 (13) | 0.356 (3) |
C32 | 0.884 (3) | 0.737 (3) | 0.7321 (12) | 0.0352 (12) | 0.356 (3) |
H32 | 0.9451 | 0.7860 | 0.7159 | 0.042* | 0.356 (3) |
C33 | 0.763 (3) | 0.683 (2) | 0.6756 (12) | 0.0345 (14) | 0.356 (3) |
H33 | 0.7045 | 0.6333 | 0.6924 | 0.041* | 0.356 (3) |
C311 | 0.9927 (19) | 0.5405 (17) | 0.851 (2) | 0.0385 (13) | 0.356 (3) |
H311 | 1.0682 | 0.5840 | 0.8382 | 0.046* | 0.356 (3) |
C312 | 1.0239 (18) | 0.4537 (15) | 0.8647 (19) | 0.0470 (11) | 0.356 (3) |
H312 | 1.1206 | 0.4386 | 0.8608 | 0.056* | 0.356 (3) |
C313 | 0.9114 (16) | 0.3855 (12) | 0.8845 (17) | 0.0501 (13) | 0.356 (3) |
H313 | 0.9311 | 0.3233 | 0.8876 | 0.060* | 0.356 (3) |
C314 | 0.7757 (16) | 0.4111 (12) | 0.8990 (17) | 0.0455 (12) | 0.356 (3) |
H314 | 0.7050 | 0.3678 | 0.9157 | 0.055* | 0.356 (3) |
C315 | 0.4254 (15) | 0.6532 (10) | 0.9175 (15) | 0.0391 (10) | 0.356 (3) |
H315 | 0.3529 | 0.6096 | 0.9326 | 0.047* | 0.356 (3) |
C316 | 0.3952 (16) | 0.7435 (10) | 0.9131 (14) | 0.0413 (12) | 0.356 (3) |
H316 | 0.3042 | 0.7624 | 0.9273 | 0.050* | 0.356 (3) |
C317 | 0.5024 (19) | 0.8090 (11) | 0.8869 (18) | 0.0407 (10) | 0.356 (3) |
H317 | 0.4805 | 0.8706 | 0.8833 | 0.049* | 0.356 (3) |
C318 | 0.637 (2) | 0.7833 (14) | 0.867 (2) | 0.0365 (10) | 0.356 (3) |
H318 | 0.7070 | 0.8287 | 0.8523 | 0.044* | 0.356 (3) |
C319 | 0.8138 (15) | 0.6609 (12) | 0.8538 (13) | 0.0312 (9) | 0.356 (3) |
C320 | 0.5989 (14) | 0.5309 (10) | 0.9031 (15) | 0.0375 (9) | 0.356 (3) |
H320 | 0.5247 | 0.4858 | 0.9155 | 0.045* | 0.356 (3) |
C321 | 0.845 (2) | 0.5661 (16) | 0.857 (3) | 0.0327 (11) | 0.356 (3) |
C322 | 0.7383 (19) | 0.5032 (15) | 0.889 (2) | 0.0366 (8) | 0.356 (3) |
C323 | 0.5666 (19) | 0.6235 (12) | 0.899 (2) | 0.0339 (8) | 0.356 (3) |
C324 | 0.671 (2) | 0.6876 (16) | 0.868 (3) | 0.0322 (6) | 0.356 (3) |
C331 | 0.7119 (16) | 0.6938 (15) | 0.5904 (8) | 0.0336 (11) | 0.356 (3) |
C332 | 0.7896 (11) | 0.7611 (10) | 0.5540 (6) | 0.0379 (7) | 0.356 (3) |
H332 | 0.8793 | 0.8019 | 0.5842 | 0.046* | 0.356 (3) |
C333 | 0.7358 (7) | 0.7684 (6) | 0.4732 (4) | 0.0399 (7) | 0.356 (3) |
H333 | 0.7904 | 0.8136 | 0.4500 | 0.048* | 0.356 (3) |
C334 | 0.6015 (7) | 0.7093 (5) | 0.4264 (3) | 0.0400 (7) | 0.356 (3) |
C335 | 0.5251 (7) | 0.6414 (5) | 0.4627 (4) | 0.0434 (8) | 0.356 (3) |
H335 | 0.4364 | 0.5998 | 0.4320 | 0.052* | 0.356 (3) |
C336 | 0.5774 (8) | 0.6341 (6) | 0.5432 (4) | 0.0393 (8) | 0.356 (3) |
H336 | 0.5224 | 0.5889 | 0.5663 | 0.047* | 0.356 (3) |
C337 | 0.5407 (6) | 0.7158 (4) | 0.3371 (3) | 0.0523 (7) | 0.356 (3) |
H337 | 0.4377 | 0.6773 | 0.3196 | 0.063* | 0.356 (3) |
C338 | 0.643 (5) | 0.671 (3) | 0.2714 (9) | 0.0767 (12) | 0.356 (3) |
H38A | 0.6069 | 0.6779 | 0.2159 | 0.115* | 0.356 (3) |
H38B | 0.6394 | 0.6015 | 0.2677 | 0.115* | 0.356 (3) |
H33C | 0.7450 | 0.7061 | 0.2899 | 0.115* | 0.356 (3) |
C339 | 0.5370 (11) | 0.8232 (7) | 0.3378 (7) | 0.105 (2) | 0.356 (3) |
H39A | 0.4816 | 0.8247 | 0.2846 | 0.158* | 0.356 (3) |
H39B | 0.6387 | 0.8584 | 0.3443 | 0.158* | 0.356 (3) |
H39C | 0.4885 | 0.8546 | 0.3849 | 0.158* | 0.356 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0341 (8) | 0.0458 (10) | 0.0339 (8) | 0.0065 (7) | 0.0038 (6) | 0.0054 (7) |
O11 | 0.0388 (7) | 0.0710 (10) | 0.0470 (7) | 0.0172 (6) | 0.0010 (5) | −0.0098 (6) |
C12 | 0.0333 (8) | 0.0402 (10) | 0.0385 (8) | 0.0069 (7) | 0.0029 (6) | 0.0030 (7) |
C13 | 0.0340 (8) | 0.0394 (9) | 0.0347 (8) | 0.0080 (6) | 0.0055 (6) | 0.0060 (7) |
C111 | 0.0733 (14) | 0.0409 (11) | 0.0443 (10) | 0.0019 (9) | −0.0023 (9) | 0.0096 (8) |
C112 | 0.103 (2) | 0.0526 (13) | 0.0551 (12) | 0.0093 (12) | −0.0021 (12) | 0.0232 (11) |
C113 | 0.0945 (18) | 0.0703 (16) | 0.0436 (11) | 0.0048 (13) | −0.0097 (11) | 0.0228 (11) |
C114 | 0.0621 (12) | 0.0557 (12) | 0.0372 (9) | −0.0015 (9) | −0.0069 (8) | 0.0054 (9) |
C115 | 0.0426 (10) | 0.0402 (10) | 0.0669 (12) | 0.0042 (8) | 0.0052 (9) | 0.0123 (9) |
C116 | 0.0509 (11) | 0.0526 (12) | 0.0834 (15) | 0.0114 (9) | 0.0116 (10) | 0.0340 (11) |
C117 | 0.0444 (10) | 0.0693 (14) | 0.0582 (11) | 0.0158 (9) | 0.0121 (8) | 0.0333 (11) |
C118 | 0.0328 (8) | 0.0566 (11) | 0.0422 (9) | 0.0081 (7) | 0.0073 (7) | 0.0155 (8) |
C119 | 0.0260 (7) | 0.0406 (9) | 0.0340 (8) | 0.0025 (6) | 0.0033 (6) | 0.0050 (7) |
C120 | 0.0316 (8) | 0.0402 (10) | 0.0410 (9) | −0.0021 (7) | −0.0001 (6) | −0.0015 (7) |
C121 | 0.0359 (8) | 0.0411 (10) | 0.0375 (8) | 0.0006 (7) | 0.0012 (6) | 0.0078 (7) |
C122 | 0.0345 (8) | 0.0436 (10) | 0.0371 (8) | −0.0012 (7) | 0.0000 (6) | 0.0061 (7) |
C123 | 0.0262 (7) | 0.0400 (9) | 0.0477 (9) | 0.0020 (6) | 0.0050 (6) | 0.0103 (7) |
C124 | 0.0229 (7) | 0.0436 (9) | 0.0396 (8) | 0.0042 (6) | 0.0060 (6) | 0.0117 (7) |
C131 | 0.0341 (8) | 0.0324 (8) | 0.0321 (8) | 0.0033 (6) | 0.0033 (6) | 0.0084 (6) |
C132 | 0.0360 (8) | 0.0368 (9) | 0.0350 (8) | 0.0009 (7) | 0.0053 (6) | −0.0021 (7) |
C133 | 0.0324 (8) | 0.0441 (10) | 0.0430 (9) | 0.0065 (7) | 0.0091 (7) | 0.0024 (8) |
C134 | 0.0345 (8) | 0.0362 (9) | 0.0323 (8) | −0.0001 (6) | 0.0042 (6) | 0.0120 (7) |
C135 | 0.0407 (9) | 0.0369 (9) | 0.0304 (8) | 0.0037 (7) | 0.0020 (6) | 0.0027 (7) |
C136 | 0.0378 (9) | 0.0386 (9) | 0.0353 (8) | 0.0097 (7) | 0.0052 (6) | 0.0029 (7) |
C137 | 0.0336 (8) | 0.0479 (10) | 0.0382 (8) | 0.0011 (7) | 0.0013 (6) | 0.0067 (7) |
C138 | 0.0333 (9) | 0.0473 (11) | 0.0949 (16) | 0.0004 (8) | 0.0018 (9) | 0.0294 (11) |
C139 | 0.0498 (11) | 0.0594 (13) | 0.0692 (13) | 0.0014 (9) | −0.0123 (10) | 0.0320 (11) |
C21 | 0.0289 (8) | 0.0351 (10) | 0.0393 (8) | 0.0075 (6) | 0.0055 (6) | 0.0073 (7) |
O21 | 0.0344 (19) | 0.0502 (8) | 0.046 (2) | −0.0007 (16) | −0.001 (2) | 0.010 (2) |
C22 | 0.0293 (18) | 0.0388 (16) | 0.0411 (9) | 0.0091 (18) | 0.0101 (9) | 0.0138 (9) |
C23 | 0.0330 (8) | 0.036 (4) | 0.0365 (8) | 0.0082 (15) | 0.0107 (6) | 0.0093 (15) |
C211 | 0.0384 (17) | 0.0397 (13) | 0.035 (4) | 0.0100 (11) | 0.0113 (12) | 0.003 (2) |
C212 | 0.044 (3) | 0.0512 (12) | 0.050 (4) | 0.0248 (19) | 0.018 (2) | 0.0079 (15) |
C213 | 0.055 (4) | 0.0447 (12) | 0.0589 (15) | 0.025 (3) | 0.014 (4) | 0.0179 (11) |
C214 | 0.053 (4) | 0.0430 (15) | 0.0487 (12) | 0.017 (2) | 0.018 (4) | 0.0179 (11) |
C215 | 0.0320 (11) | 0.053 (4) | 0.0346 (10) | 0.0083 (18) | 0.0064 (10) | 0.015 (3) |
C216 | 0.0313 (10) | 0.055 (4) | 0.0394 (10) | 0.016 (2) | 0.0055 (7) | 0.011 (3) |
C217 | 0.0403 (17) | 0.044 (4) | 0.0405 (10) | 0.017 (3) | 0.0026 (13) | 0.012 (3) |
C218 | 0.0358 (16) | 0.039 (4) | 0.0338 (11) | 0.007 (2) | 0.0021 (16) | 0.009 (4) |
C219 | 0.0310 (8) | 0.035 (2) | 0.0246 (17) | 0.0045 (10) | 0.0025 (8) | 0.0036 (18) |
C220 | 0.037 (2) | 0.043 (2) | 0.0362 (16) | 0.0079 (12) | 0.008 (2) | 0.0168 (17) |
C221 | 0.031 (2) | 0.0375 (11) | 0.027 (2) | 0.0063 (14) | 0.000 (3) | 0.0055 (7) |
C222 | 0.040 (3) | 0.040 (2) | 0.0331 (8) | 0.0126 (13) | 0.010 (3) | 0.0109 (19) |
C223 | 0.0322 (12) | 0.039 (4) | 0.0300 (9) | 0.0087 (16) | 0.0046 (10) | 0.008 (3) |
C224 | 0.0304 (9) | 0.039 (3) | 0.0270 (15) | 0.0079 (14) | 0.0006 (10) | 0.010 (3) |
C231 | 0.0298 (19) | 0.037 (5) | 0.0360 (9) | 0.0092 (12) | 0.0104 (9) | 0.0099 (18) |
C232 | 0.025 (3) | 0.046 (3) | 0.0436 (13) | 0.0042 (16) | 0.0064 (13) | 0.0144 (15) |
C233 | 0.032 (2) | 0.044 (2) | 0.0473 (13) | 0.0029 (14) | 0.0112 (14) | 0.0195 (15) |
C234 | 0.0310 (19) | 0.047 (2) | 0.0451 (12) | 0.0090 (13) | 0.0074 (13) | 0.0159 (15) |
C235 | 0.0305 (14) | 0.056 (3) | 0.0450 (11) | 0.0028 (17) | 0.0042 (10) | 0.0187 (18) |
C236 | 0.0304 (11) | 0.048 (3) | 0.0421 (10) | 0.0039 (17) | 0.0100 (8) | 0.0164 (16) |
C237 | 0.0462 (17) | 0.062 (2) | 0.0557 (15) | 0.0058 (12) | 0.0034 (13) | 0.0323 (15) |
C238 | 0.095 (4) | 0.092 (2) | 0.0423 (11) | 0.0142 (16) | 0.0016 (12) | 0.0234 (12) |
C239 | 0.083 (4) | 0.170 (5) | 0.116 (3) | 0.066 (4) | 0.028 (4) | 0.105 (4) |
C31 | 0.0289 (8) | 0.0351 (10) | 0.0393 (8) | 0.0075 (6) | 0.0055 (6) | 0.0073 (7) |
O31 | 0.0344 (19) | 0.0502 (8) | 0.046 (2) | −0.0007 (16) | −0.001 (2) | 0.010 (2) |
C32 | 0.0293 (18) | 0.0388 (16) | 0.0411 (9) | 0.0091 (18) | 0.0101 (9) | 0.0138 (9) |
C33 | 0.0330 (8) | 0.036 (4) | 0.0365 (8) | 0.0082 (15) | 0.0107 (6) | 0.0093 (15) |
C311 | 0.0384 (17) | 0.0397 (13) | 0.035 (4) | 0.0100 (11) | 0.0113 (12) | 0.003 (2) |
C312 | 0.044 (3) | 0.0512 (12) | 0.050 (4) | 0.0248 (19) | 0.018 (2) | 0.0079 (15) |
C313 | 0.055 (4) | 0.0447 (12) | 0.0589 (15) | 0.025 (3) | 0.014 (4) | 0.0179 (11) |
C314 | 0.053 (4) | 0.0430 (15) | 0.0487 (12) | 0.017 (2) | 0.018 (4) | 0.0179 (11) |
C315 | 0.0320 (11) | 0.053 (4) | 0.0346 (10) | 0.0083 (18) | 0.0064 (10) | 0.015 (3) |
C316 | 0.0313 (10) | 0.055 (4) | 0.0394 (10) | 0.016 (2) | 0.0055 (7) | 0.011 (3) |
C317 | 0.0403 (17) | 0.044 (4) | 0.0405 (10) | 0.017 (3) | 0.0026 (13) | 0.012 (3) |
C318 | 0.0358 (16) | 0.039 (4) | 0.0338 (11) | 0.007 (2) | 0.0021 (16) | 0.009 (4) |
C319 | 0.0310 (8) | 0.035 (2) | 0.0246 (17) | 0.0045 (10) | 0.0025 (8) | 0.0036 (18) |
C320 | 0.037 (2) | 0.043 (2) | 0.0362 (16) | 0.0079 (12) | 0.008 (2) | 0.0168 (17) |
C321 | 0.031 (2) | 0.0375 (11) | 0.027 (2) | 0.0063 (14) | 0.000 (3) | 0.0055 (7) |
C322 | 0.040 (3) | 0.040 (2) | 0.0331 (8) | 0.0126 (13) | 0.010 (3) | 0.0109 (19) |
C323 | 0.0322 (12) | 0.039 (4) | 0.0300 (9) | 0.0087 (16) | 0.0046 (10) | 0.008 (3) |
C324 | 0.0304 (9) | 0.039 (3) | 0.0270 (15) | 0.0079 (14) | 0.0006 (10) | 0.010 (3) |
C331 | 0.0298 (19) | 0.037 (5) | 0.0360 (9) | 0.0092 (12) | 0.0104 (9) | 0.0099 (18) |
C332 | 0.025 (3) | 0.046 (3) | 0.0436 (13) | 0.0042 (16) | 0.0064 (13) | 0.0144 (15) |
C333 | 0.032 (2) | 0.044 (2) | 0.0473 (13) | 0.0029 (14) | 0.0112 (14) | 0.0195 (15) |
C334 | 0.0310 (19) | 0.047 (2) | 0.0451 (12) | 0.0090 (13) | 0.0074 (13) | 0.0159 (15) |
C335 | 0.0305 (14) | 0.056 (3) | 0.0450 (11) | 0.0028 (17) | 0.0042 (10) | 0.0187 (18) |
C336 | 0.0304 (11) | 0.048 (3) | 0.0421 (10) | 0.0039 (17) | 0.0100 (8) | 0.0164 (16) |
C337 | 0.0462 (17) | 0.062 (2) | 0.0557 (15) | 0.0058 (12) | 0.0034 (13) | 0.0323 (15) |
C338 | 0.095 (4) | 0.092 (2) | 0.0423 (11) | 0.0142 (16) | 0.0016 (12) | 0.0234 (12) |
C339 | 0.083 (4) | 0.170 (5) | 0.116 (3) | 0.066 (4) | 0.028 (4) | 0.105 (4) |
C11—O11 | 1.215 (2) | C219—C221 | 1.413 (3) |
C11—C12 | 1.473 (2) | C220—C223 | 1.390 (3) |
C11—C119 | 1.509 (2) | C220—C222 | 1.392 (3) |
C12—C13 | 1.332 (2) | C220—H220 | 0.9300 |
C12—H12 | 0.9300 | C221—C222 | 1.441 (3) |
C13—C131 | 1.460 (2) | C223—C224 | 1.435 (3) |
C13—H13 | 0.9300 | C231—C232 | 1.393 (4) |
C111—C112 | 1.358 (3) | C231—C236 | 1.394 (4) |
C111—C121 | 1.425 (3) | C232—C233 | 1.383 (3) |
C111—H111 | 0.9300 | C232—H232 | 0.9300 |
C112—C113 | 1.412 (3) | C233—C234 | 1.394 (4) |
C112—H112 | 0.9300 | C233—H233 | 0.9300 |
C113—C114 | 1.347 (3) | C234—C235 | 1.392 (4) |
C113—H113 | 0.9300 | C234—C237 | 1.523 (3) |
C114—C122 | 1.423 (3) | C235—C236 | 1.382 (3) |
C114—H114 | 0.9300 | C235—H235 | 0.9300 |
C115—C116 | 1.352 (3) | C236—H236 | 0.9300 |
C115—C123 | 1.419 (3) | C237—C239 | 1.507 (5) |
C115—H115 | 0.9300 | C237—C238 | 1.545 (11) |
C116—C117 | 1.413 (3) | C237—H237 | 0.9800 |
C116—H116 | 0.9300 | C238—H28A | 0.9600 |
C117—C118 | 1.359 (3) | C238—H28B | 0.9600 |
C117—H117 | 0.9300 | C238—H28C | 0.9600 |
C118—C124 | 1.426 (2) | C239—H29A | 0.9600 |
C118—H118 | 0.9300 | C239—H29B | 0.9600 |
C119—C121 | 1.405 (2) | C239—H29C | 0.9600 |
C119—C124 | 1.406 (2) | C31—O31 | 1.221 (4) |
C120—C122 | 1.386 (3) | C31—C32 | 1.468 (4) |
C120—C123 | 1.393 (3) | C31—C319 | 1.510 (4) |
C120—H120 | 0.9300 | C32—C33 | 1.345 (6) |
C121—C122 | 1.440 (2) | C32—H32 | 0.9300 |
C123—C124 | 1.436 (2) | C33—C331 | 1.465 (4) |
C131—C132 | 1.392 (2) | C33—H33 | 0.9300 |
C131—C136 | 1.395 (2) | C311—C312 | 1.356 (4) |
C132—C133 | 1.376 (2) | C311—C321 | 1.433 (5) |
C132—H132 | 0.9300 | C311—H311 | 0.9300 |
C133—C134 | 1.390 (2) | C312—C313 | 1.417 (5) |
C133—H133 | 0.9300 | C312—H312 | 0.9300 |
C134—C135 | 1.386 (2) | C313—C314 | 1.349 (5) |
C134—C137 | 1.517 (2) | C313—H313 | 0.9300 |
C135—C136 | 1.387 (2) | C314—C322 | 1.427 (4) |
C135—H135 | 0.9300 | C314—H314 | 0.9300 |
C136—H136 | 0.9300 | C315—C316 | 1.353 (5) |
C137—C139 | 1.518 (3) | C315—C323 | 1.430 (4) |
C137—C138 | 1.526 (3) | C315—H315 | 0.9300 |
C137—H137 | 0.9800 | C316—C317 | 1.416 (5) |
C138—H18A | 0.9600 | C316—H316 | 0.9300 |
C138—H18B | 0.9600 | C317—C318 | 1.358 (4) |
C138—H18C | 0.9600 | C317—H317 | 0.9300 |
C139—H19A | 0.9600 | C318—C324 | 1.429 (5) |
C139—H19B | 0.9600 | C318—H318 | 0.9300 |
C139—H19C | 0.9600 | C319—C324 | 1.412 (4) |
C21—O21 | 1.222 (3) | C319—C321 | 1.414 (5) |
C21—C22 | 1.466 (3) | C320—C323 | 1.390 (4) |
C21—C219 | 1.509 (3) | C320—C322 | 1.390 (4) |
C22—C23 | 1.346 (5) | C320—H320 | 0.9300 |
C22—H22 | 0.9300 | C321—C322 | 1.443 (4) |
C23—C231 | 1.467 (3) | C323—C324 | 1.436 (4) |
C23—H23 | 0.9300 | C331—C332 | 1.390 (5) |
C211—C212 | 1.356 (3) | C331—C336 | 1.396 (5) |
C211—C221 | 1.432 (4) | C332—C333 | 1.387 (4) |
C211—H211 | 0.9300 | C332—H332 | 0.9300 |
C212—C213 | 1.417 (4) | C333—C334 | 1.390 (5) |
C212—H212 | 0.9300 | C333—H333 | 0.9300 |
C213—C214 | 1.350 (4) | C334—C335 | 1.389 (5) |
C213—H213 | 0.9300 | C334—C337 | 1.528 (4) |
C214—C222 | 1.428 (3) | C335—C336 | 1.380 (5) |
C214—H214 | 0.9300 | C335—H335 | 0.9300 |
C215—C216 | 1.354 (4) | C336—H336 | 0.9300 |
C215—C223 | 1.430 (3) | C337—C339 | 1.511 (6) |
C215—H215 | 0.9300 | C337—C338 | 1.549 (13) |
C216—C217 | 1.417 (4) | C337—H337 | 0.9800 |
C216—H216 | 0.9300 | C338—H38A | 0.9600 |
C217—C218 | 1.358 (3) | C338—H38B | 0.9600 |
C217—H217 | 0.9300 | C338—H33C | 0.9600 |
C218—C224 | 1.428 (3) | C339—H39A | 0.9600 |
C218—H218 | 0.9300 | C339—H39B | 0.9600 |
C219—C224 | 1.411 (3) | C339—H39C | 0.9600 |
O11—C11—C12 | 123.20 (16) | C214—C222—C221 | 118.5 (2) |
O11—C11—C119 | 120.18 (15) | C220—C223—C215 | 122.1 (3) |
C12—C11—C119 | 116.61 (14) | C220—C223—C224 | 119.4 (3) |
C13—C12—C11 | 121.47 (16) | C215—C223—C224 | 118.5 (2) |
C13—C12—H12 | 119.3 | C219—C224—C218 | 122.9 (3) |
C11—C12—H12 | 119.3 | C219—C224—C223 | 119.0 (2) |
C12—C13—C131 | 127.53 (16) | C218—C224—C223 | 118.1 (2) |
C12—C13—H13 | 116.2 | C232—C231—C236 | 117.9 (2) |
C131—C13—H13 | 116.2 | C232—C231—C23 | 122.7 (3) |
C112—C111—C121 | 121.36 (19) | C236—C231—C23 | 119.4 (3) |
C112—C111—H111 | 119.3 | C233—C232—C231 | 120.4 (3) |
C121—C111—H111 | 119.3 | C233—C232—H232 | 119.8 |
C111—C112—C113 | 120.6 (2) | C231—C232—H232 | 119.8 |
C111—C112—H112 | 119.7 | C232—C233—C234 | 121.8 (3) |
C113—C112—H112 | 119.7 | C232—C233—H233 | 119.1 |
C114—C113—C112 | 120.14 (19) | C234—C233—H233 | 119.1 |
C114—C113—H113 | 119.9 | C235—C234—C233 | 117.6 (2) |
C112—C113—H113 | 119.9 | C235—C234—C237 | 122.2 (3) |
C113—C114—C122 | 121.74 (18) | C233—C234—C237 | 120.2 (3) |
C113—C114—H114 | 119.1 | C236—C235—C234 | 120.8 (3) |
C122—C114—H114 | 119.1 | C236—C235—H235 | 119.6 |
C116—C115—C123 | 121.54 (19) | C234—C235—H235 | 119.6 |
C116—C115—H115 | 119.2 | C235—C236—C231 | 121.5 (3) |
C123—C115—H115 | 119.2 | C235—C236—H236 | 119.3 |
C115—C116—C117 | 120.09 (19) | C231—C236—H236 | 119.3 |
C115—C116—H116 | 120.0 | C239—C237—C234 | 112.7 (3) |
C117—C116—H116 | 120.0 | C239—C237—C238 | 110.2 (9) |
C118—C117—C116 | 120.72 (18) | C234—C237—C238 | 110.5 (4) |
C118—C117—H117 | 119.6 | C239—C237—H237 | 107.7 |
C116—C117—H117 | 119.6 | C234—C237—H237 | 107.7 |
C117—C118—C124 | 121.02 (18) | C238—C237—H237 | 107.7 |
C117—C118—H118 | 119.5 | C237—C238—H28A | 109.5 |
C124—C118—H118 | 119.5 | C237—C238—H28B | 109.5 |
C121—C119—C124 | 121.64 (15) | H28A—C238—H28B | 109.5 |
C121—C119—C11 | 119.09 (15) | C237—C238—H28C | 109.5 |
C124—C119—C11 | 119.28 (14) | H28A—C238—H28C | 109.5 |
C122—C120—C123 | 122.30 (15) | H28B—C238—H28C | 109.5 |
C122—C120—H120 | 118.9 | C237—C239—H29A | 109.5 |
C123—C120—H120 | 118.9 | C237—C239—H29B | 109.5 |
C119—C121—C111 | 123.58 (16) | H29A—C239—H29B | 109.5 |
C119—C121—C122 | 118.70 (16) | C237—C239—H29C | 109.5 |
C111—C121—C122 | 117.71 (16) | H29A—C239—H29C | 109.5 |
C120—C122—C114 | 122.24 (16) | H29B—C239—H29C | 109.5 |
C120—C122—C121 | 119.33 (16) | O31—C31—C32 | 120.0 (5) |
C114—C122—C121 | 118.43 (17) | O31—C31—C319 | 120.1 (5) |
C120—C123—C115 | 122.21 (17) | C32—C31—C319 | 119.8 (5) |
C120—C123—C124 | 119.17 (16) | C33—C32—C31 | 124.1 (7) |
C115—C123—C124 | 118.62 (16) | C33—C32—H32 | 118.0 |
C119—C124—C118 | 123.16 (16) | C31—C32—H32 | 118.0 |
C119—C124—C123 | 118.85 (15) | C32—C33—C331 | 127.1 (7) |
C118—C124—C123 | 117.99 (16) | C32—C33—H33 | 116.4 |
C132—C131—C136 | 117.53 (15) | C331—C33—H33 | 116.4 |
C132—C131—C13 | 122.65 (15) | C312—C311—C321 | 120.9 (5) |
C136—C131—C13 | 119.81 (15) | C312—C311—H311 | 119.5 |
C133—C132—C131 | 121.31 (15) | C321—C311—H311 | 119.5 |
C133—C132—H132 | 119.3 | C311—C312—C313 | 121.0 (5) |
C131—C132—H132 | 119.3 | C311—C312—H312 | 119.5 |
C132—C133—C134 | 121.27 (16) | C313—C312—H312 | 119.5 |
C132—C133—H133 | 119.4 | C314—C313—C312 | 119.9 (5) |
C134—C133—H133 | 119.4 | C314—C313—H313 | 120.0 |
C135—C134—C133 | 117.76 (15) | C312—C313—H313 | 120.0 |
C135—C134—C137 | 120.87 (15) | C313—C314—C322 | 121.4 (5) |
C133—C134—C137 | 121.37 (15) | C313—C314—H314 | 119.3 |
C134—C135—C136 | 121.19 (15) | C322—C314—H314 | 119.3 |
C134—C135—H135 | 119.4 | C316—C315—C323 | 121.4 (5) |
C136—C135—H135 | 119.4 | C316—C315—H315 | 119.3 |
C135—C136—C131 | 120.92 (16) | C323—C315—H315 | 119.3 |
C135—C136—H136 | 119.5 | C315—C316—C317 | 119.8 (5) |
C131—C136—H136 | 119.5 | C315—C316—H316 | 120.1 |
C134—C137—C139 | 113.05 (15) | C317—C316—H316 | 120.1 |
C134—C137—C138 | 110.88 (15) | C318—C317—C316 | 121.1 (5) |
C139—C137—C138 | 109.53 (16) | C318—C317—H317 | 119.5 |
C134—C137—H137 | 107.7 | C316—C317—H317 | 119.5 |
C139—C137—H137 | 107.7 | C317—C318—C324 | 121.0 (5) |
C138—C137—H137 | 107.7 | C317—C318—H318 | 119.5 |
C137—C138—H18A | 109.5 | C324—C318—H318 | 119.5 |
C137—C138—H18B | 109.5 | C324—C319—C321 | 121.0 (5) |
H18A—C138—H18B | 109.5 | C324—C319—C31 | 120.4 (5) |
C137—C138—H18C | 109.5 | C321—C319—C31 | 117.7 (5) |
H18A—C138—H18C | 109.5 | C323—C320—C322 | 122.3 (5) |
H18B—C138—H18C | 109.5 | C323—C320—H320 | 118.9 |
C137—C139—H19A | 109.5 | C322—C320—H320 | 118.9 |
C137—C139—H19B | 109.5 | C319—C321—C311 | 122.2 (8) |
H19A—C139—H19B | 109.5 | C319—C321—C322 | 118.6 (5) |
C137—C139—H19C | 109.5 | C311—C321—C322 | 117.3 (6) |
H19A—C139—H19C | 109.5 | C320—C322—C314 | 122.4 (5) |
H19B—C139—H19C | 109.5 | C320—C322—C321 | 118.9 (4) |
O21—C21—C22 | 119.9 (3) | C314—C322—C321 | 118.5 (4) |
O21—C21—C219 | 119.8 (3) | C320—C323—C315 | 122.0 (5) |
C22—C21—C219 | 120.2 (3) | C320—C323—C324 | 119.2 (4) |
C23—C22—C21 | 125.1 (5) | C315—C323—C324 | 118.6 (4) |
C23—C22—H22 | 117.4 | C319—C324—C318 | 122.6 (6) |
C21—C22—H22 | 117.4 | C319—C324—C323 | 118.8 (5) |
C22—C23—C231 | 125.7 (4) | C318—C324—C323 | 117.7 (5) |
C22—C23—H23 | 117.1 | C332—C331—C336 | 117.8 (4) |
C231—C23—H23 | 117.1 | C332—C331—C33 | 123.7 (5) |
C212—C211—C221 | 120.8 (3) | C336—C331—C33 | 118.5 (5) |
C212—C211—H211 | 119.6 | C333—C332—C331 | 121.2 (5) |
C221—C211—H211 | 119.6 | C333—C332—H332 | 119.4 |
C211—C212—C213 | 120.9 (3) | C331—C332—H332 | 119.4 |
C211—C212—H212 | 119.5 | C332—C333—C334 | 121.1 (5) |
C213—C212—H212 | 119.5 | C332—C333—H333 | 119.5 |
C214—C213—C212 | 120.2 (3) | C334—C333—H333 | 119.5 |
C214—C213—H213 | 119.9 | C335—C334—C333 | 117.5 (4) |
C212—C213—H213 | 119.9 | C335—C334—C337 | 120.6 (5) |
C213—C214—C222 | 121.3 (3) | C333—C334—C337 | 121.9 (5) |
C213—C214—H214 | 119.4 | C336—C335—C334 | 121.8 (4) |
C222—C214—H214 | 119.4 | C336—C335—H335 | 119.1 |
C216—C215—C223 | 121.5 (3) | C334—C335—H335 | 119.1 |
C216—C215—H215 | 119.3 | C335—C336—C331 | 120.7 (5) |
C223—C215—H215 | 119.3 | C335—C336—H336 | 119.7 |
C215—C216—C217 | 120.0 (3) | C331—C336—H336 | 119.7 |
C215—C216—H216 | 120.0 | C339—C337—C334 | 110.9 (5) |
C217—C216—H216 | 120.0 | C339—C337—C338 | 109.2 (12) |
C218—C217—C216 | 120.8 (3) | C334—C337—C338 | 109.6 (6) |
C218—C217—H217 | 119.6 | C339—C337—H337 | 109.0 |
C216—C217—H217 | 119.6 | C334—C337—H337 | 109.0 |
C217—C218—C224 | 121.1 (3) | C338—C337—H337 | 109.0 |
C217—C218—H218 | 119.4 | C337—C338—H38A | 109.5 |
C224—C218—H218 | 119.4 | C337—C338—H38B | 109.5 |
C224—C219—C221 | 120.7 (3) | H38A—C338—H38B | 109.5 |
C224—C219—C21 | 120.6 (3) | C337—C338—H33C | 109.5 |
C221—C219—C21 | 117.9 (3) | H38A—C338—H33C | 109.5 |
C223—C220—C222 | 122.2 (3) | H38B—C338—H33C | 109.5 |
C223—C220—H220 | 118.9 | C337—C339—H39A | 109.5 |
C222—C220—H220 | 118.9 | C337—C339—H39B | 109.5 |
C219—C221—C211 | 122.8 (3) | H39A—C339—H39B | 109.5 |
C219—C221—C222 | 118.8 (3) | C337—C339—H39C | 109.5 |
C211—C221—C222 | 117.8 (3) | H39A—C339—H39C | 109.5 |
C220—C222—C214 | 122.3 (3) | H39B—C339—H39C | 109.5 |
C220—C222—C221 | 119.1 (3) | ||
O11—C11—C12—C13 | −3.2 (3) | C216—C215—C223—C220 | 176.6 (13) |
C119—C11—C12—C13 | 177.72 (16) | C216—C215—C223—C224 | 0 (2) |
C11—C12—C13—C131 | 179.25 (17) | C221—C219—C224—C218 | 172.8 (19) |
C121—C111—C112—C113 | 0.5 (4) | C21—C219—C224—C218 | 4 (3) |
C111—C112—C113—C114 | 0.0 (4) | C221—C219—C224—C223 | −10 (3) |
C112—C113—C114—C122 | −0.5 (4) | C21—C219—C224—C223 | −179.4 (14) |
C123—C115—C116—C117 | −0.2 (3) | C217—C218—C224—C219 | 179.0 (18) |
C115—C116—C117—C118 | 0.0 (3) | C217—C218—C224—C223 | 2 (3) |
C116—C117—C118—C124 | 1.1 (3) | C220—C223—C224—C219 | 6 (3) |
O11—C11—C119—C121 | −66.5 (2) | C215—C223—C224—C219 | −178.0 (16) |
C12—C11—C119—C121 | 112.60 (18) | C220—C223—C224—C218 | −177.0 (18) |
O11—C11—C119—C124 | 113.3 (2) | C215—C223—C224—C218 | −1 (3) |
C12—C11—C119—C124 | −67.5 (2) | C22—C23—C231—C232 | −1 (3) |
C124—C119—C121—C111 | −178.78 (18) | C22—C23—C231—C236 | 179.3 (19) |
C11—C119—C121—C111 | 1.1 (3) | C236—C231—C232—C233 | 0.2 (15) |
C124—C119—C121—C122 | 1.3 (2) | C23—C231—C232—C233 | −179.3 (13) |
C11—C119—C121—C122 | −178.81 (15) | C231—C232—C233—C234 | −0.6 (12) |
C112—C111—C121—C119 | 179.5 (2) | C232—C233—C234—C235 | 0.3 (7) |
C112—C111—C121—C122 | −0.6 (3) | C232—C233—C234—C237 | −177.3 (5) |
C123—C120—C122—C114 | 179.13 (18) | C233—C234—C235—C236 | 0.4 (6) |
C123—C120—C122—C121 | −0.5 (3) | C237—C234—C235—C236 | 178.0 (3) |
C113—C114—C122—C120 | −179.2 (2) | C234—C235—C236—C231 | −0.9 (8) |
C113—C114—C122—C121 | 0.4 (3) | C232—C231—C236—C235 | 0.6 (14) |
C119—C121—C122—C120 | −0.3 (2) | C23—C231—C236—C235 | −180.0 (12) |
C111—C121—C122—C120 | 179.76 (18) | C235—C234—C237—C239 | 50.0 (5) |
C119—C121—C122—C114 | −179.99 (17) | C233—C234—C237—C239 | −132.5 (5) |
C111—C121—C122—C114 | 0.1 (3) | C235—C234—C237—C238 | −73.9 (11) |
C122—C120—C123—C115 | −179.93 (17) | C233—C234—C237—C238 | 103.7 (12) |
C122—C120—C123—C124 | 0.4 (3) | O31—C31—C32—C33 | 170 (6) |
C116—C115—C123—C120 | 179.68 (18) | C319—C31—C32—C33 | −12 (5) |
C116—C115—C123—C124 | −0.6 (3) | C31—C32—C33—C331 | 178 (3) |
C121—C119—C124—C118 | 177.72 (15) | C321—C311—C312—C313 | 0 (5) |
C11—C119—C124—C118 | −2.1 (2) | C311—C312—C313—C314 | −7 (5) |
C121—C119—C124—C123 | −1.4 (2) | C312—C313—C314—C322 | 4 (5) |
C11—C119—C124—C123 | 178.69 (14) | C323—C315—C316—C317 | 2 (4) |
C117—C118—C124—C119 | 178.90 (16) | C315—C316—C317—C318 | −1 (4) |
C117—C118—C124—C123 | −1.9 (2) | C316—C317—C318—C324 | 3 (5) |
C120—C123—C124—C119 | 0.6 (2) | O31—C31—C319—C324 | 116 (5) |
C115—C123—C124—C119 | −179.11 (15) | C32—C31—C319—C324 | −61 (4) |
C120—C123—C124—C118 | −178.63 (15) | O31—C31—C319—C321 | −75 (5) |
C115—C123—C124—C118 | 1.7 (2) | C32—C31—C319—C321 | 107 (3) |
C12—C13—C131—C132 | −4.1 (3) | C324—C319—C321—C311 | −174 (3) |
C12—C13—C131—C136 | 175.54 (17) | C31—C319—C321—C311 | 18 (4) |
C136—C131—C132—C133 | −0.5 (3) | C324—C319—C321—C322 | −10 (5) |
C13—C131—C132—C133 | 179.11 (17) | C31—C319—C321—C322 | −178 (3) |
C131—C132—C133—C134 | −0.1 (3) | C312—C311—C321—C319 | 172 (3) |
C132—C133—C134—C135 | 0.5 (3) | C312—C311—C321—C322 | 8 (5) |
C132—C133—C134—C137 | −179.87 (17) | C323—C320—C322—C314 | 175 (3) |
C133—C134—C135—C136 | −0.3 (3) | C323—C320—C322—C321 | −9 (5) |
C137—C134—C135—C136 | −179.92 (16) | C313—C314—C322—C320 | 180 (3) |
C134—C135—C136—C131 | −0.3 (3) | C313—C314—C322—C321 | 4 (5) |
C132—C131—C136—C135 | 0.8 (3) | C319—C321—C322—C320 | 9 (5) |
C13—C131—C136—C135 | −178.92 (16) | C311—C321—C322—C320 | 174 (3) |
C135—C134—C137—C139 | −137.63 (18) | C319—C321—C322—C314 | −175 (3) |
C133—C134—C137—C139 | 42.8 (2) | C311—C321—C322—C314 | −10 (5) |
C135—C134—C137—C138 | 98.9 (2) | C322—C320—C323—C315 | −177 (3) |
C133—C134—C137—C138 | −80.7 (2) | C322—C320—C323—C324 | 9 (5) |
O21—C21—C22—C23 | −172 (3) | C316—C315—C323—C320 | −180 (3) |
C219—C21—C22—C23 | 11 (3) | C316—C315—C323—C324 | −6 (5) |
C21—C22—C23—C231 | 173.8 (18) | C321—C319—C324—C318 | 179 (4) |
C221—C211—C212—C213 | 3 (3) | C31—C319—C324—C318 | −13 (5) |
C211—C212—C213—C214 | 3 (2) | C321—C319—C324—C323 | 10 (5) |
C212—C213—C214—C222 | −5 (2) | C31—C319—C324—C323 | 178 (3) |
C223—C215—C216—C217 | −1 (2) | C317—C318—C324—C319 | −175 (3) |
C215—C216—C217—C218 | 2 (2) | C317—C318—C324—C323 | −6 (6) |
C216—C217—C218—C224 | −3 (3) | C320—C323—C324—C319 | −9 (5) |
O21—C21—C219—C224 | 106 (3) | C315—C323—C324—C319 | 177 (3) |
C22—C21—C219—C224 | −77.3 (19) | C320—C323—C324—C318 | −178 (3) |
O21—C21—C219—C221 | −64 (3) | C315—C323—C324—C318 | 7 (5) |
C22—C21—C219—C221 | 113.1 (16) | C32—C33—C331—C332 | 3 (6) |
C224—C219—C221—C211 | −178.3 (18) | C32—C33—C331—C336 | −176 (4) |
C21—C219—C221—C211 | −9 (2) | C336—C331—C332—C333 | 0 (3) |
C224—C219—C221—C222 | 10 (2) | C33—C331—C332—C333 | −180 (3) |
C21—C219—C221—C222 | −180.0 (13) | C331—C332—C333—C334 | 1 (2) |
C212—C211—C221—C219 | −178.4 (17) | C332—C333—C334—C335 | −1.3 (14) |
C212—C211—C221—C222 | −7 (3) | C332—C333—C334—C337 | −179.7 (10) |
C223—C220—C222—C214 | 178.9 (15) | C333—C334—C335—C336 | 1.7 (12) |
C223—C220—C222—C221 | 3 (3) | C337—C334—C335—C336 | −179.9 (7) |
C213—C214—C222—C220 | −175.6 (15) | C334—C335—C336—C331 | −1.4 (18) |
C213—C214—C222—C221 | 1 (3) | C332—C331—C336—C335 | 1 (3) |
C219—C221—C222—C220 | −7 (3) | C33—C331—C336—C335 | −180 (2) |
C211—C221—C222—C220 | −178.3 (17) | C335—C334—C337—C339 | 131.4 (7) |
C219—C221—C222—C214 | 177.0 (16) | C333—C334—C337—C339 | −50.3 (9) |
C211—C221—C222—C214 | 5 (3) | C335—C334—C337—C338 | −108 (2) |
C222—C220—C223—C215 | −178.2 (15) | C333—C334—C337—C338 | 70 (2) |
C222—C220—C223—C224 | −2 (3) |
Cg1 and Cg2 are the centroids of rings (C111–C114/C122/C111) and (C114–C118/C124/C113), respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C133—H133···O11i | 0.93 | 2.49 | 3.336 (2) | 151 |
C216—H216···O21i | 0.93 | 2.61 | 3.41 (2) | 144 |
C216—H216···O31i | 0.93 | 2.58 | 3.36 (4) | 142 |
C316—H316···O21i | 0.93 | 2.51 | 3.30 (3) | 144 |
C316—H316···O31i | 0.93 | 2.47 | 3.25 (4) | 142 |
C233—H233···Cg1ii | 0.93 | 2.64 | 3.355 (4) | 134 |
C236—H236···Cg2iii | 0.93 | 2.75 | 3.519 (4) | 140 |
C336—H336···Cg2iii | 0.93 | 2.80 | 3.354 (7) | 119 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+1. |
Acknowledgements
MG thanks the UGC for the award of a Rajeev Gandhi fellowship and HSY thanks the University of Mysore for research facilities. JPJ acknowledges the NSF–MRI program (grant No. 1039027) for funds to purchase the X-ray diffractometer.
References
Agarwal, A., Srivastava, K., Puri, S. K. & Chauhan, P. M. S. (2005). Bioorg. Med. Chem. 13, 4645–4650. Web of Science CrossRef PubMed CAS Google Scholar
Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England. Google Scholar
Baktır, Z., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1292–o1293. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cobo, D., Quiroga, J., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o3639–o3641. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
Fang, Q., Zhao, L., Wang, Y., Zhang, Y., Li, Z., Pan, Y., Kanchana, K., Wang, J., Tong, C., Li, D. & Liang, G. (2015). Toxicol. Appl. Pharmacol. 282, 129–138. CrossRef CAS PubMed Google Scholar
Glidewell, C. & Lloyd, D. (1984). Tetrahedron, 40, 4455–4472. CrossRef CAS Web of Science Google Scholar
Glidewell, C. & Lloyd, D. (1986). J. Chem. Educ. 63, 306–309. CrossRef CAS Google Scholar
Insuasty, H., Insuasty, B., Castro, E., Cobo, J. & Glidewell, C. (2014). Acta Cryst. C70, 908–911. CSD CrossRef IUCr Journals Google Scholar
Kant, R., Sharma, R., Salian, V. V., Sarojini, B. K. & Narayana, B. (2015). Eur. Chem. Bull. 4, 327–330. CAS Google Scholar
Kumar, D., Maruthi Kumar, N., Tantak, M. P., Ogura, M., Kusaka, E. & Ito, T. (2014). Bioorg. Med. Chem. Lett. 24, 5170–5174. CrossRef CAS PubMed Google Scholar
López, S. N., Castelli, M. V., Zacchino, S. A., Domínguez, J. N., Lobo, G., Charris-Charris, J., Cortés, J. C. G., Ribas, J. C., Devia, C., Rodríguez, A. M. & Enriz, R. D. (2001). Bioorg. Med. Chem. 9, 1999–2013. PubMed Google Scholar
Mohan, B. J., Sarojini, B. K., Yathirajan, H. S., Rathore, R. & Glidewell, C. (2016). Acta Cryst. E72, 31–34. CSD CrossRef IUCr Journals Google Scholar
Naik, V. S., Shettigar, V., Berglin, T. S., Coburn, J. S., Jasinski, J. P. & Yathirajan, H. S. (2015). Acta Cryst. E71, 965–971. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naik, V. S., Yathirajan, H. S., Jasinski, J. P., Smolenski, V. A. & Glidewell, C. (2015). Acta Cryst. E71, 1093–1099. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nayak, P. S., Narayana, B., Yathirajan, H. S., Hosten, E. C., Betz, R. & Glidewell, C. (2014). Acta Cryst. C70, 1011–1016. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salian, V. V., Narayana, B., Yathirajan, H. S., Akkurt, M., Çelik, Ö., Ersanlı, C. C. & Glidewell, C. (2015). Acta Cryst. C71, 610–617. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salian, V. V., Narayana, B., Yathirajan, H. S., Rathore, R. S., Jasinski, J. P. & Glidewell, C. (2016). Private communication (refcode: CCDC 1481314). CCDC, Cambridge, England. Google Scholar
Samshuddin, S., Jasinski, J. P., Butcher, R. J., Neuhardt, E. A., Narayana, B., Yathirajan, H. S. & Glidewell, C. (2014). Acta Cryst. C70, 953–959. Web of Science CSD CrossRef IUCr Journals Google Scholar
Samshuddin, S., Narayana, B., Sarojini, B. K., Yathirajan, H. S. & Raghavendra, R. (2012). Pharma Chemica, 4, 1445–1457. CAS Google Scholar
Samshuddin, S., Narayana, B., Shetty, D. N. & Raghavendra, R. (2011). Pharma Chemica, 3, 232–240. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Syam, S., Abdelwahab, S. I., Al-Mamary, M. A. & Mohan, S. (2012). Molecules, 17, 6179–6195. CrossRef CAS PubMed Google Scholar
Tran, T.-D., Nguyen, T.-T.-N., Do, T.-H., Huynh, T.-N.-P., Tran, C.-D. & Thai, K.-M. (2012). Molecules, 17, 6684–6696. CrossRef CAS PubMed Google Scholar
Trilleras, J., Quiroga, J., Cobo, J. & Glidewell, C. (2009). Acta Cryst. C65, o284–o286. Web of Science CSD CrossRef IUCr Journals Google Scholar
Trilleras, J., Quiroga, J., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. E61, o1892–o1894. Web of Science CSD CrossRef IUCr Journals 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.