research communications
of ethyl 4-[(4-methylbenzyl)oxy]benzoate
aDepartment of Chemistry, Rajshahi University, Rajshahi-6205, Bangladesh, bCenter for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan, cDepartment of Applied Science, Faculty of Science, Okayama University of Science, Japan, and dDepartment of Chemical and Pharmaceutical Sciences, University of Trieste, Italy
*Correspondence e-mail: ansary_chem@ru.ac.bd
The title compound, C17H18O3, crystallizes with three molecules in the The molecules differ in the conformation related to the ethoxy group and in the orientation of the two phenyl rings, one of which has the ethoxy group disordered over two positions with refined occupancies of 0.735:0.265 (9). In the crystal packing, the molecules are connected by weak C—H⋯π interactions.
Keywords: crystal structure; ester; ether; conformational flexibility.
CCDC reference: 2174691
1. Chemical context
Alkylbenzoates are an important class of compounds with interesting physical properties and applications in industry. For example, 4-hydroxybenzoic acid and its et al., 1999; Yang et al., 2014).
are widely used as preservatives in cosmetic and pharmaceutical products known as parabens, for which the physical properties and crystal structures have been widely described (GiordanoAlkylbenzoates of different properties have been designed, amongst other things, with the aim of preparing liquid crystalline compounds (Abser et al., 1993), functionalized poly(benzyl ether) dendrimers with methyl ester decorations as efficient organogelators (Feng et al., 2009), or non-linear optical materials (Perumal et al., 2002). Moreover, the ester bond has a prominent position in cell biology and medicinal chemistry (Lavis, 2008), and carbohydrazones can be obtained by reacting corresponding with suitable hydrazine derivatives.
We report here the synthesis and
of another example of a derivatized alkylbenzoate with an ether group.2. Structural commentary
Three molecules, which slightly differ in their conformations, are present in the –3). The main conformational differences of molecules A, B and C are related to the ethoxy group with C—O—CH2—CH3 torsion angles of 174.0 (6), 82.6 (6) and 89.6 (7)°, and in the orientation of the two phenyl rings that form a dihedral angle of 46.4 (1), 70.3 (1), and 62.2 (1)°, respectively. A side view of the molecules displayed in Fig. 4 highlights these differences. All these features are indicative of the conformational freedom of this molecule. Nevertheless, all bond lengths and angles in the three molecules relating to the ether and the ester groups are similar within their standard uncertainties. In general, bond lengths (Allen et al., 1987) and angles are within normal ranges. In molecule C, the ethoxy group O9/C5/C51 is disordered over two sets of sites (Fig. 3).
of the title compound (Figs. 1In the parent methyl 4-(benzyloxy)-3-methoxybenzoate compound, which is an important organic intermediate for the synthesis of the antineoplastic drug Cediranib (Wang et al., 2013), the two aromatic rings are almost normal to each other forming a dihedral angle of 85.81 (10)° and bond lengths are close comparable with those determined here.
3. Supramolecular features
Despite the number of phenyl rings, the aromatic rings have rather distant centroid-to-centroid distances of between 4.727 (3) and 4.946 (3) Å, but with unsuitable orientations for efficient π-stacking interactions. On the other hand, the crystal packing indicates a series of C—H⋯π ring interactions in the range 2.65–2.94 Å (Table 1), as derived with PLATON (Spek, 2020). A view of the is displayed in Fig. 5, showing these kinds of interactions. In addition, non-conventional C—H⋯O hydrogen bonds are observed in the crystal packing (Table 2).
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4. Database survey
The conformations of the three independent molecules present in the ) and 69.19 (6)° (Qin et al., 2019). However, a few structures exhibit almost coplanar orientations of the phenyl rings (Jasinski et al., 2008; Feng et al., 2009), or small dihedral angles such as the 4.1 (2) and 10.9 (4)° reported for 3,5-bis(benzyloxy)benzoic acid (Moreno-Fuquen et al. 2012). The latter conformations favour electron delocalization between the two rings, but packing requirements also play a role.
of the title compound agree with previous structurally characterized species containing the (benzyloxy)phenyl fragment, where the two aromatic rings form dihedral angles of 64.5 (2)° (mean value of two independent molecules; Bats & Canenbley, 19845. Synthesis and crystallization
A mixture of ethyl-4-hydroxybenzoate (8.75 g, 52.65 mmol) and 4-methylbenzylbromide (9.75 g, 52.68 mmol) in acetone (100 ml) was refluxed for 14 h over anhydrous potassium carbonate (20 g). The solvent was removed in vacuo, and the remaining solid was dissolved in water and extracted with dichloromethane. Left overnight, colourless needle-shaped crystals were formed, filtered off, washed, and dried over silica gel in a desiccator. Yield: 12.58 g, 88% Melting point: 323 −324 K. FT–IR: 1706 ν (C=O), 1258, 1276 ν (C—Oester), 1106, 1102 ν (C—Oether). 1H NMR (CDCl3,600 MHz): δ = 1.37 (t, 3H, CH3CH2-, J = 10.5 Hz), 2.36 (s, 3H, C6H4–CH3),4.35 (q, 2H, CH3–CH2, J = 10.5 Hz), 5.07 (s, 2H, C6H4–CH2–), 6.98 (d, 2H, H-5,6, J =7.8 Hz), 7.20 (d, 2H, H-10,11, J = 11.4 Hz), 7.31 (d, 2H, H-8,9, J = 12 Hz), 7.99 (d, 2H, H-3,4, J = 6.6 Hz), ppm. 13C NMR (CDCl3, 600 MHz): 14.4 (C11), 21.3 (C7), 60.7 (C10), 70.1 (C8), 114.4 (C-3,5), 123.15 (C1), 127.73 (C-2′,6′), 129.1 (C-3′,5′), 131.6 (C-2,6), 133.31 (C1′),138.13 (C4), 162.5 (C4′), 166.4 (C9), ppm. LC–MS (ESI) m/z: [M + H]+. Calculated for C17H18O3 271.13; found 271.13.
6. Refinement
Crystal data, data collection and structure . The structure was refined as a two-component The –OCH2CH3 moiety of molecule C was found to be disordered over two sets of sites with refined occupancies of 0.735 (9):0.265 (9). For modelling the minor disordered part, all atoms were refined with isotropic displacement parameters, and C—C and C—O bond lengths were restrained by using DFIX commands.
details are summarized in Table 3Supporting information
CCDC reference: 2174691
https://doi.org/10.1107/S2056989022009380/wm5660sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022009380/wm5660Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009380/wm5660Isup3.cml
Data collection: CrystalStructure (Rigaku, 2018); cell
CrystalStructure (Rigaku, 2018); data reduction: CrystalStructure (Rigaku, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012).C17H18O3 | F(000) = 864 |
Mr = 270.31 | Dx = 1.242 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71075 Å |
a = 16.1906 (10) Å | Cell parameters from 13948 reflections |
b = 7.5752 (4) Å | θ = 2.3–27.5° |
c = 17.7591 (9) Å | µ = 0.08 mm−1 |
β = 95.360 (7)° | T = 173 K |
V = 2168.6 (2) Å3 | Prism, colorless |
Z = 6 | 0.30 × 0.20 × 0.05 mm |
Rigaku R-AXIS RAPID diffractometer | 5301 reflections with I > 2σ(I) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.042 |
ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.533, Tmax = 0.996 | k = −9→9 |
16200 measured reflections | l = −21→21 |
7609 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0667P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.125 | (Δ/σ)max = 0.001 |
S = 0.97 | Δρmax = 0.16 e Å−3 |
7609 reflections | Δρmin = −0.17 e Å−3 |
560 parameters | Absolute structure: Refined as an inversion twin |
5 restraints | Absolute structure parameter: 0.6 (14) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.10822 (15) | 0.3014 (4) | 0.12187 (14) | 0.0520 (7) | |
O2 | 0.19050 (18) | 0.4249 (6) | 0.47508 (17) | 0.0864 (12) | |
O3 | 0.06054 (17) | 0.3271 (5) | 0.47163 (14) | 0.0648 (8) | |
O4 | 0.24935 (14) | 0.7272 (4) | 1.05090 (15) | 0.0496 (7) | |
O5 | 0.14434 (17) | 0.5821 (4) | 0.70340 (16) | 0.0648 (8) | |
O6 | 0.26005 (16) | 0.7442 (4) | 0.69644 (15) | 0.0625 (8) | |
O7 | 0.40986 (15) | 0.2922 (3) | 1.18050 (15) | 0.0510 (7) | |
O8 | 0.44677 (16) | 0.0780 (4) | 0.83691 (16) | 0.0599 (8) | |
C1 | 0.0495 (2) | 0.2152 (5) | −0.0013 (2) | 0.0443 (9) | |
C2 | −0.0147 (2) | 0.2495 (5) | −0.0573 (2) | 0.0489 (10) | |
H2 | −0.066049 | 0.293542 | −0.043362 | 0.059* | |
C3 | −0.0046 (2) | 0.2202 (6) | −0.1331 (2) | 0.0543 (11) | |
H3 | −0.049429 | 0.242504 | −0.170299 | 0.065* | |
C4 | 0.0702 (2) | 0.1589 (6) | −0.1552 (2) | 0.0497 (10) | |
C5 | 0.1338 (2) | 0.1273 (6) | −0.0996 (2) | 0.0527 (10) | |
H5 | 0.185817 | 0.087533 | −0.113626 | 0.063* | |
C6 | 0.1236 (2) | 0.1522 (6) | −0.0237 (2) | 0.0510 (10) | |
H6 | 0.167989 | 0.125624 | 0.013392 | 0.061* | |
C7 | 0.0823 (3) | 0.1340 (7) | −0.2379 (2) | 0.0659 (13) | |
H7A | 0.029618 | 0.098181 | −0.265425 | 0.079* | |
H7B | 0.124086 | 0.042428 | −0.243164 | 0.079* | |
H7C | 0.100868 | 0.245290 | −0.258874 | 0.079* | |
C8 | 0.0345 (2) | 0.2349 (6) | 0.0806 (2) | 0.0482 (10) | |
H8A | −0.012131 | 0.317425 | 0.085443 | 0.058* | |
H8B | 0.019711 | 0.119154 | 0.101448 | 0.058* | |
C9 | 0.1080 (2) | 0.3143 (6) | 0.1992 (2) | 0.0461 (9) | |
C10 | 0.1767 (2) | 0.3941 (6) | 0.2365 (2) | 0.0558 (11) | |
H10 | 0.219776 | 0.438259 | 0.208893 | 0.067* | |
C11 | 0.1824 (2) | 0.4095 (6) | 0.3143 (2) | 0.0578 (11) | |
H11 | 0.229986 | 0.463783 | 0.339851 | 0.069* | |
C12 | 0.1200 (2) | 0.3471 (6) | 0.3559 (2) | 0.0498 (10) | |
C13 | 0.0515 (2) | 0.2667 (5) | 0.3178 (2) | 0.0497 (10) | |
H13 | 0.008507 | 0.222475 | 0.345492 | 0.060* | |
C14 | 0.0448 (2) | 0.2498 (5) | 0.2392 (2) | 0.0487 (10) | |
H14 | −0.002383 | 0.194827 | 0.213432 | 0.058* | |
C15 | 0.1293 (2) | 0.3687 (7) | 0.4396 (2) | 0.0584 (12) | |
C16 | 0.0629 (3) | 0.3580 (9) | 0.5529 (2) | 0.0770 (15) | |
H16A | 0.079550 | 0.481406 | 0.564682 | 0.092* | |
H16B | 0.103932 | 0.278330 | 0.580244 | 0.092* | |
C17 | −0.0198 (3) | 0.3242 (9) | 0.5765 (3) | 0.0857 (16) | |
H17A | −0.059461 | 0.407351 | 0.551013 | 0.103* | |
H17B | −0.018733 | 0.339427 | 0.631386 | 0.103* | |
H17C | −0.036552 | 0.203129 | 0.562945 | 0.103* | |
C18 | 0.3073 (2) | 0.8300 (5) | 1.1705 (2) | 0.0478 (10) | |
C19 | 0.3626 (2) | 0.7371 (6) | 1.2195 (2) | 0.0524 (10) | |
H19 | 0.406274 | 0.672221 | 1.200302 | 0.063* | |
C20 | 0.3545 (2) | 0.7383 (6) | 1.2969 (2) | 0.0583 (11) | |
H20 | 0.393475 | 0.675592 | 1.330204 | 0.070* | |
C21 | 0.2907 (3) | 0.8295 (6) | 1.3260 (2) | 0.0594 (11) | |
C22 | 0.2347 (3) | 0.9185 (6) | 1.2765 (3) | 0.0628 (12) | |
H22 | 0.189626 | 0.979302 | 1.295321 | 0.075* | |
C23 | 0.2433 (2) | 0.9204 (6) | 1.1995 (2) | 0.0572 (11) | |
H23 | 0.204792 | 0.984611 | 1.166346 | 0.069* | |
C24 | 0.2827 (3) | 0.8334 (8) | 1.4110 (2) | 0.0822 (16) | |
H24A | 0.336608 | 0.806262 | 1.438416 | 0.099* | |
H24B | 0.241827 | 0.745422 | 1.423610 | 0.099* | |
H24C | 0.264674 | 0.951011 | 1.425594 | 0.099* | |
C25 | 0.3159 (2) | 0.8310 (6) | 1.0874 (2) | 0.0523 (10) | |
H25A | 0.312822 | 0.953494 | 1.067897 | 0.063* | |
H25B | 0.370048 | 0.780204 | 1.077218 | 0.063* | |
C26 | 0.2446 (2) | 0.7150 (5) | 0.9736 (2) | 0.0432 (9) | |
C27 | 0.1790 (2) | 0.6128 (5) | 0.9411 (2) | 0.0470 (10) | |
H27 | 0.142358 | 0.556082 | 0.972200 | 0.056* | |
C28 | 0.1676 (2) | 0.5945 (5) | 0.8635 (2) | 0.0489 (10) | |
H28 | 0.122810 | 0.525418 | 0.841335 | 0.059* | |
C29 | 0.2212 (2) | 0.6763 (5) | 0.8173 (2) | 0.0457 (9) | |
C30 | 0.2876 (2) | 0.7729 (5) | 0.8507 (2) | 0.0476 (10) | |
H30 | 0.325151 | 0.826994 | 0.819724 | 0.057* | |
C31 | 0.3002 (2) | 0.7918 (5) | 0.9286 (2) | 0.0476 (10) | |
H31 | 0.346440 | 0.856677 | 0.950938 | 0.057* | |
C32 | 0.2039 (2) | 0.6608 (6) | 0.7346 (2) | 0.0517 (10) | |
C33 | 0.2436 (3) | 0.7472 (8) | 0.6140 (2) | 0.0743 (15) | |
H33A | 0.220428 | 0.632046 | 0.596184 | 0.089* | |
H33B | 0.296151 | 0.766405 | 0.590866 | 0.089* | |
C34 | 0.1840 (3) | 0.8902 (10) | 0.5902 (3) | 0.0973 (19) | |
H34A | 0.174983 | 0.892892 | 0.534905 | 0.117* | |
H34B | 0.206633 | 1.003831 | 0.608704 | 0.117* | |
H34C | 0.131214 | 0.868111 | 0.611367 | 0.117* | |
C35 | 0.4655 (2) | 0.2889 (5) | 1.3101 (2) | 0.0491 (10) | |
C36 | 0.5264 (2) | 0.3902 (6) | 1.3491 (2) | 0.0564 (11) | |
H36 | 0.574469 | 0.421203 | 1.325178 | 0.068* | |
C37 | 0.5190 (3) | 0.4475 (6) | 1.4222 (3) | 0.0598 (11) | |
H37 | 0.562457 | 0.514344 | 1.448032 | 0.072* | |
C38 | 0.4486 (3) | 0.4081 (6) | 1.4581 (2) | 0.0572 (11) | |
C39 | 0.3864 (3) | 0.3103 (6) | 1.4183 (2) | 0.0602 (11) | |
H39 | 0.337265 | 0.283573 | 1.441409 | 0.072* | |
C40 | 0.3948 (2) | 0.2508 (6) | 1.3455 (2) | 0.0579 (11) | |
H40 | 0.351576 | 0.183268 | 1.319594 | 0.070* | |
C41 | 0.4391 (3) | 0.4632 (7) | 1.5379 (2) | 0.0780 (14) | |
H41A | 0.380484 | 0.456245 | 1.547340 | 0.094* | |
H41B | 0.458706 | 0.584850 | 1.545643 | 0.094* | |
H41C | 0.471799 | 0.384621 | 1.572923 | 0.094* | |
C42 | 0.4754 (2) | 0.2209 (6) | 1.2318 (2) | 0.0536 (10) | |
H42A | 0.529913 | 0.257174 | 1.216028 | 0.064* | |
H42B | 0.472692 | 0.090338 | 1.231359 | 0.064* | |
C43 | 0.4135 (2) | 0.2591 (5) | 1.1059 (2) | 0.0462 (10) | |
C44 | 0.3508 (2) | 0.3376 (5) | 1.0580 (2) | 0.0493 (10) | |
H44 | 0.308706 | 0.404410 | 1.078743 | 0.059* | |
C45 | 0.3497 (2) | 0.3187 (5) | 0.9804 (2) | 0.0531 (10) | |
H45 | 0.307418 | 0.374312 | 0.948115 | 0.064* | |
C46 | 0.4106 (2) | 0.2179 (5) | 0.9493 (2) | 0.0476 (10) | |
C47 | 0.4712 (2) | 0.1361 (5) | 0.9978 (2) | 0.0482 (10) | |
H47 | 0.511533 | 0.064016 | 0.977267 | 0.058* | |
C48 | 0.4739 (2) | 0.1577 (5) | 1.0761 (2) | 0.0464 (9) | |
H48 | 0.516601 | 0.103709 | 1.108483 | 0.056* | |
C49 | 0.4124 (2) | 0.1963 (6) | 0.8672 (3) | 0.0584 (11) | |
O9 | 0.3807 (3) | 0.3384 (6) | 0.8254 (2) | 0.0544 (16) | 0.735 (9) |
C50 | 0.3807 (5) | 0.3379 (13) | 0.7433 (6) | 0.064 (2) | 0.735 (9) |
H50A | 0.432423 | 0.282505 | 0.729022 | 0.077* | 0.735 (9) |
H50B | 0.378868 | 0.460869 | 0.724260 | 0.077* | 0.735 (9) |
C51 | 0.3068 (4) | 0.2372 (9) | 0.7079 (4) | 0.067 (2) | 0.735 (9) |
H51A | 0.307393 | 0.237694 | 0.652755 | 0.101* | 0.735 (9) |
H51B | 0.309176 | 0.115223 | 0.726315 | 0.101* | 0.735 (9) |
H51C | 0.255724 | 0.293246 | 0.721562 | 0.101* | 0.735 (9) |
O9B | 0.3346 (8) | 0.2613 (17) | 0.8386 (6) | 0.056 (4)* | 0.265 (9) |
C50B | 0.3182 (13) | 0.228 (3) | 0.7576 (11) | 0.078 (6)* | 0.265 (9) |
H50C | 0.260686 | 0.263008 | 0.740216 | 0.093* | 0.265 (9) |
H50D | 0.324382 | 0.100218 | 0.747293 | 0.093* | 0.265 (9) |
C51B | 0.377 (2) | 0.330 (5) | 0.7170 (19) | 0.081 (12)* | 0.265 (9) |
H51D | 0.366615 | 0.307989 | 0.662536 | 0.122* | 0.265 (9) |
H51E | 0.370481 | 0.455896 | 0.727113 | 0.122* | 0.265 (9) |
H51F | 0.433994 | 0.293573 | 0.734169 | 0.122* | 0.265 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0389 (14) | 0.0603 (19) | 0.0572 (17) | −0.0066 (13) | 0.0069 (11) | −0.0051 (15) |
O2 | 0.0544 (19) | 0.136 (4) | 0.069 (2) | −0.016 (2) | 0.0050 (15) | −0.028 (2) |
O3 | 0.0547 (17) | 0.085 (2) | 0.0546 (17) | −0.0051 (17) | 0.0072 (13) | −0.0107 (17) |
O4 | 0.0407 (14) | 0.0462 (16) | 0.0617 (18) | −0.0072 (13) | 0.0043 (12) | 0.0012 (14) |
O5 | 0.0518 (17) | 0.072 (2) | 0.0698 (19) | −0.0104 (17) | 0.0028 (14) | −0.0147 (17) |
O6 | 0.0508 (16) | 0.079 (2) | 0.0583 (18) | −0.0110 (16) | 0.0111 (13) | −0.0097 (16) |
O7 | 0.0411 (14) | 0.0503 (17) | 0.0619 (18) | 0.0051 (13) | 0.0060 (12) | 0.0001 (15) |
O8 | 0.0538 (16) | 0.0573 (19) | 0.0695 (19) | 0.0051 (15) | 0.0096 (13) | −0.0054 (16) |
C1 | 0.039 (2) | 0.036 (2) | 0.058 (2) | −0.0038 (18) | 0.0085 (17) | −0.0015 (19) |
C2 | 0.040 (2) | 0.045 (2) | 0.063 (3) | −0.0003 (18) | 0.0106 (18) | 0.002 (2) |
C3 | 0.046 (2) | 0.056 (3) | 0.060 (3) | −0.007 (2) | −0.0004 (18) | 0.007 (2) |
C4 | 0.051 (2) | 0.043 (2) | 0.056 (2) | −0.0052 (19) | 0.0115 (19) | 0.002 (2) |
C5 | 0.042 (2) | 0.052 (3) | 0.066 (3) | 0.0035 (19) | 0.0130 (19) | −0.002 (2) |
C6 | 0.041 (2) | 0.052 (2) | 0.061 (3) | 0.0001 (19) | 0.0054 (18) | 0.003 (2) |
C7 | 0.078 (3) | 0.063 (3) | 0.058 (3) | −0.016 (3) | 0.014 (2) | −0.004 (2) |
C8 | 0.040 (2) | 0.050 (2) | 0.055 (2) | −0.0056 (19) | 0.0085 (17) | −0.002 (2) |
C9 | 0.040 (2) | 0.047 (2) | 0.052 (2) | 0.0026 (19) | 0.0081 (16) | −0.004 (2) |
C10 | 0.044 (2) | 0.060 (3) | 0.066 (3) | −0.008 (2) | 0.0137 (19) | −0.008 (2) |
C11 | 0.044 (2) | 0.059 (3) | 0.071 (3) | −0.009 (2) | 0.0030 (19) | −0.012 (2) |
C12 | 0.041 (2) | 0.052 (3) | 0.056 (2) | 0.003 (2) | 0.0038 (17) | −0.006 (2) |
C13 | 0.040 (2) | 0.050 (3) | 0.059 (3) | −0.0032 (19) | 0.0079 (17) | −0.003 (2) |
C14 | 0.037 (2) | 0.052 (3) | 0.056 (3) | −0.0034 (19) | 0.0025 (17) | −0.008 (2) |
C15 | 0.045 (2) | 0.069 (3) | 0.061 (3) | 0.003 (2) | 0.003 (2) | −0.012 (2) |
C16 | 0.072 (3) | 0.112 (4) | 0.048 (3) | 0.004 (3) | 0.005 (2) | −0.010 (3) |
C17 | 0.086 (4) | 0.111 (5) | 0.061 (3) | −0.012 (3) | 0.012 (2) | −0.002 (3) |
C18 | 0.041 (2) | 0.039 (2) | 0.063 (3) | −0.0033 (19) | 0.0035 (18) | 0.001 (2) |
C19 | 0.042 (2) | 0.049 (3) | 0.066 (3) | 0.004 (2) | 0.0088 (18) | 0.000 (2) |
C20 | 0.049 (2) | 0.058 (3) | 0.067 (3) | 0.000 (2) | −0.0007 (19) | 0.011 (2) |
C21 | 0.063 (3) | 0.053 (3) | 0.063 (3) | −0.011 (2) | 0.011 (2) | −0.001 (2) |
C22 | 0.055 (3) | 0.058 (3) | 0.077 (3) | 0.008 (2) | 0.014 (2) | −0.009 (3) |
C23 | 0.051 (2) | 0.053 (3) | 0.067 (3) | 0.006 (2) | 0.001 (2) | −0.004 (2) |
C24 | 0.093 (4) | 0.088 (4) | 0.067 (3) | −0.011 (3) | 0.019 (3) | −0.003 (3) |
C25 | 0.040 (2) | 0.055 (3) | 0.062 (3) | −0.007 (2) | 0.0046 (17) | −0.007 (2) |
C26 | 0.0363 (19) | 0.038 (2) | 0.056 (2) | 0.0034 (18) | 0.0050 (16) | −0.0020 (19) |
C27 | 0.033 (2) | 0.040 (2) | 0.069 (3) | 0.0010 (17) | 0.0104 (18) | 0.000 (2) |
C28 | 0.0320 (19) | 0.041 (2) | 0.073 (3) | 0.0008 (18) | 0.0020 (18) | −0.005 (2) |
C29 | 0.0339 (19) | 0.043 (2) | 0.060 (3) | 0.0045 (17) | 0.0030 (17) | −0.005 (2) |
C30 | 0.039 (2) | 0.043 (2) | 0.062 (3) | −0.0006 (18) | 0.0115 (17) | −0.003 (2) |
C31 | 0.036 (2) | 0.044 (2) | 0.062 (3) | −0.0045 (17) | 0.0033 (17) | −0.004 (2) |
C32 | 0.039 (2) | 0.051 (3) | 0.065 (3) | 0.000 (2) | 0.0068 (19) | −0.013 (2) |
C33 | 0.064 (3) | 0.105 (4) | 0.056 (3) | −0.018 (3) | 0.018 (2) | −0.022 (3) |
C34 | 0.084 (4) | 0.141 (6) | 0.067 (3) | 0.000 (4) | 0.006 (3) | 0.009 (4) |
C35 | 0.041 (2) | 0.043 (2) | 0.064 (3) | 0.0045 (18) | 0.0064 (18) | 0.006 (2) |
C36 | 0.043 (2) | 0.050 (3) | 0.076 (3) | −0.003 (2) | 0.006 (2) | 0.007 (2) |
C37 | 0.051 (2) | 0.050 (3) | 0.077 (3) | −0.007 (2) | −0.003 (2) | 0.000 (2) |
C38 | 0.060 (3) | 0.048 (3) | 0.063 (3) | 0.000 (2) | 0.001 (2) | 0.000 (2) |
C39 | 0.050 (2) | 0.063 (3) | 0.070 (3) | −0.005 (2) | 0.018 (2) | 0.000 (2) |
C40 | 0.042 (2) | 0.057 (3) | 0.075 (3) | −0.009 (2) | 0.0052 (19) | −0.001 (2) |
C41 | 0.093 (4) | 0.068 (3) | 0.073 (3) | 0.001 (3) | 0.009 (3) | −0.008 (3) |
C42 | 0.039 (2) | 0.057 (3) | 0.065 (3) | 0.004 (2) | 0.0051 (18) | 0.006 (2) |
C43 | 0.0341 (19) | 0.040 (2) | 0.066 (3) | −0.0026 (18) | 0.0103 (17) | −0.003 (2) |
C44 | 0.036 (2) | 0.042 (2) | 0.070 (3) | 0.0046 (18) | 0.0045 (18) | −0.005 (2) |
C45 | 0.040 (2) | 0.042 (2) | 0.075 (3) | 0.0058 (19) | −0.0065 (18) | −0.006 (2) |
C46 | 0.039 (2) | 0.041 (2) | 0.061 (3) | −0.0001 (19) | −0.0004 (17) | −0.006 (2) |
C47 | 0.037 (2) | 0.036 (2) | 0.073 (3) | 0.0008 (18) | 0.0074 (18) | −0.002 (2) |
C48 | 0.0339 (19) | 0.042 (2) | 0.063 (3) | −0.0001 (18) | 0.0018 (17) | 0.003 (2) |
C49 | 0.049 (2) | 0.052 (3) | 0.072 (3) | 0.009 (2) | −0.005 (2) | −0.011 (2) |
O9 | 0.061 (3) | 0.046 (3) | 0.056 (3) | 0.008 (2) | 0.0020 (18) | 0.001 (2) |
C50 | 0.058 (4) | 0.062 (5) | 0.074 (7) | −0.006 (3) | 0.012 (4) | −0.005 (5) |
C51 | 0.052 (4) | 0.064 (4) | 0.084 (6) | −0.003 (3) | −0.002 (3) | 0.000 (4) |
O1—C9 | 1.377 (4) | C25—H25B | 0.9900 |
O1—C8 | 1.432 (4) | C26—C31 | 1.387 (5) |
O2—C15 | 1.201 (5) | C26—C27 | 1.395 (5) |
O3—C15 | 1.335 (5) | C27—C28 | 1.380 (5) |
O3—C16 | 1.459 (4) | C27—H27 | 0.9500 |
O4—C26 | 1.371 (4) | C28—C29 | 1.393 (5) |
O4—C25 | 1.438 (4) | C28—H28 | 0.9500 |
O5—C32 | 1.222 (4) | C29—C30 | 1.387 (5) |
O6—C32 | 1.341 (5) | C29—C32 | 1.475 (5) |
O6—C33 | 1.463 (5) | C30—C31 | 1.387 (5) |
O7—C43 | 1.355 (4) | C30—H30 | 0.9500 |
O7—C42 | 1.438 (4) | C31—H31 | 0.9500 |
O8—C49 | 1.207 (5) | C33—C34 | 1.485 (8) |
C1—C6 | 1.383 (5) | C33—H33A | 0.9900 |
C1—C2 | 1.393 (5) | C33—H33B | 0.9900 |
C1—C8 | 1.505 (5) | C34—H34A | 0.9800 |
C2—C3 | 1.390 (5) | C34—H34B | 0.9800 |
C2—H2 | 0.9500 | C34—H34C | 0.9800 |
C3—C4 | 1.387 (5) | C35—C36 | 1.384 (5) |
C3—H3 | 0.9500 | C35—C40 | 1.387 (5) |
C4—C5 | 1.379 (5) | C35—C42 | 1.505 (5) |
C4—C7 | 1.512 (5) | C36—C37 | 1.384 (6) |
C5—C6 | 1.386 (5) | C36—H36 | 0.9500 |
C5—H5 | 0.9500 | C37—C38 | 1.389 (6) |
C6—H6 | 0.9500 | C37—H37 | 0.9500 |
C7—H7A | 0.9800 | C38—C39 | 1.389 (6) |
C7—H7B | 0.9800 | C38—C41 | 1.500 (6) |
C7—H7C | 0.9800 | C39—C40 | 1.388 (6) |
C8—H8A | 0.9900 | C39—H39 | 0.9500 |
C8—H8B | 0.9900 | C40—H40 | 0.9500 |
C9—C10 | 1.380 (5) | C41—H41A | 0.9800 |
C9—C14 | 1.388 (5) | C41—H41B | 0.9800 |
C10—C11 | 1.380 (5) | C41—H41C | 0.9800 |
C10—H10 | 0.9500 | C42—H42A | 0.9900 |
C11—C12 | 1.389 (5) | C42—H42B | 0.9900 |
C11—H11 | 0.9500 | C43—C48 | 1.387 (5) |
C12—C13 | 1.386 (5) | C43—C44 | 1.395 (5) |
C12—C15 | 1.488 (5) | C44—C45 | 1.384 (5) |
C13—C14 | 1.395 (5) | C44—H44 | 0.9500 |
C13—H13 | 0.9500 | C45—C46 | 1.401 (5) |
C14—H14 | 0.9500 | C45—H45 | 0.9500 |
C16—C17 | 1.463 (6) | C46—C47 | 1.389 (5) |
C16—H16A | 0.9900 | C46—C49 | 1.471 (6) |
C16—H16B | 0.9900 | C47—C48 | 1.397 (5) |
C17—H17A | 0.9800 | C47—H47 | 0.9500 |
C17—H17B | 0.9800 | C48—H48 | 0.9500 |
C17—H17C | 0.9800 | C49—O9 | 1.379 (6) |
C18—C23 | 1.381 (5) | C49—O9B | 1.403 (12) |
C18—C19 | 1.382 (5) | O9—C50 | 1.458 (11) |
C18—C25 | 1.495 (5) | C50—C51 | 1.507 (10) |
C19—C20 | 1.394 (5) | C50—H50A | 0.9900 |
C19—H19 | 0.9500 | C50—H50B | 0.9900 |
C20—C21 | 1.383 (6) | C51—H51A | 0.9800 |
C20—H20 | 0.9500 | C51—H51B | 0.9800 |
C21—C22 | 1.379 (6) | C51—H51C | 0.9800 |
C21—C24 | 1.527 (5) | O9B—C50B | 1.459 (19) |
C22—C23 | 1.388 (5) | C50B—C51B | 1.47 (2) |
C22—H22 | 0.9500 | C50B—H50C | 0.9900 |
C23—H23 | 0.9500 | C50B—H50D | 0.9900 |
C24—H24A | 0.9800 | C51B—H51D | 0.9800 |
C24—H24B | 0.9800 | C51B—H51E | 0.9800 |
C24—H24C | 0.9800 | C51B—H51F | 0.9800 |
C25—H25A | 0.9900 | ||
C9—O1—C8 | 117.1 (3) | C27—C28—H28 | 119.6 |
C15—O3—C16 | 115.9 (3) | C29—C28—H28 | 119.6 |
C26—O4—C25 | 117.3 (3) | C30—C29—C28 | 118.9 (4) |
C32—O6—C33 | 116.3 (3) | C30—C29—C32 | 122.4 (3) |
C43—O7—C42 | 117.0 (3) | C28—C29—C32 | 118.7 (3) |
C6—C1—C2 | 117.9 (4) | C31—C30—C29 | 121.1 (3) |
C6—C1—C8 | 122.3 (3) | C31—C30—H30 | 119.4 |
C2—C1—C8 | 119.6 (3) | C29—C30—H30 | 119.4 |
C3—C2—C1 | 120.9 (3) | C26—C31—C30 | 119.2 (4) |
C3—C2—H2 | 119.5 | C26—C31—H31 | 120.4 |
C1—C2—H2 | 119.5 | C30—C31—H31 | 120.4 |
C4—C3—C2 | 120.8 (4) | O5—C32—O6 | 123.0 (4) |
C4—C3—H3 | 119.6 | O5—C32—C29 | 124.0 (4) |
C2—C3—H3 | 119.6 | O6—C32—C29 | 113.0 (3) |
C5—C4—C3 | 117.9 (4) | O6—C33—C34 | 110.4 (4) |
C5—C4—C7 | 121.3 (4) | O6—C33—H33A | 109.6 |
C3—C4—C7 | 120.8 (4) | C34—C33—H33A | 109.6 |
C4—C5—C6 | 121.6 (4) | O6—C33—H33B | 109.6 |
C4—C5—H5 | 119.2 | C34—C33—H33B | 109.6 |
C6—C5—H5 | 119.2 | H33A—C33—H33B | 108.1 |
C1—C6—C5 | 120.7 (4) | C33—C34—H34A | 109.5 |
C1—C6—H6 | 119.6 | C33—C34—H34B | 109.5 |
C5—C6—H6 | 119.6 | H34A—C34—H34B | 109.5 |
C4—C7—H7A | 109.5 | C33—C34—H34C | 109.5 |
C4—C7—H7B | 109.5 | H34A—C34—H34C | 109.5 |
H7A—C7—H7B | 109.5 | H34B—C34—H34C | 109.5 |
C4—C7—H7C | 109.5 | C36—C35—C40 | 118.0 (4) |
H7A—C7—H7C | 109.5 | C36—C35—C42 | 121.3 (3) |
H7B—C7—H7C | 109.5 | C40—C35—C42 | 120.7 (4) |
O1—C8—C1 | 109.1 (3) | C35—C36—C37 | 121.5 (4) |
O1—C8—H8A | 109.9 | C35—C36—H36 | 119.2 |
C1—C8—H8A | 109.9 | C37—C36—H36 | 119.2 |
O1—C8—H8B | 109.9 | C36—C37—C38 | 120.7 (4) |
C1—C8—H8B | 109.9 | C36—C37—H37 | 119.7 |
H8A—C8—H8B | 108.3 | C38—C37—H37 | 119.7 |
O1—C9—C10 | 115.7 (3) | C37—C38—C39 | 118.0 (4) |
O1—C9—C14 | 123.8 (3) | C37—C38—C41 | 122.4 (4) |
C10—C9—C14 | 120.5 (4) | C39—C38—C41 | 119.6 (4) |
C9—C10—C11 | 119.6 (4) | C40—C39—C38 | 121.1 (4) |
C9—C10—H10 | 120.2 | C40—C39—H39 | 119.4 |
C11—C10—H10 | 120.2 | C38—C39—H39 | 119.4 |
C10—C11—C12 | 121.3 (4) | C35—C40—C39 | 120.8 (4) |
C10—C11—H11 | 119.3 | C35—C40—H40 | 119.6 |
C12—C11—H11 | 119.3 | C39—C40—H40 | 119.6 |
C13—C12—C11 | 118.6 (4) | C38—C41—H41A | 109.5 |
C13—C12—C15 | 122.5 (4) | C38—C41—H41B | 109.5 |
C11—C12—C15 | 118.9 (4) | H41A—C41—H41B | 109.5 |
C12—C13—C14 | 120.8 (4) | C38—C41—H41C | 109.5 |
C12—C13—H13 | 119.6 | H41A—C41—H41C | 109.5 |
C14—C13—H13 | 119.6 | H41B—C41—H41C | 109.5 |
C9—C14—C13 | 119.2 (3) | O7—C42—C35 | 108.7 (3) |
C9—C14—H14 | 120.4 | O7—C42—H42A | 109.9 |
C13—C14—H14 | 120.4 | C35—C42—H42A | 109.9 |
O2—C15—O3 | 122.7 (4) | O7—C42—H42B | 109.9 |
O2—C15—C12 | 124.3 (4) | C35—C42—H42B | 109.9 |
O3—C15—C12 | 112.9 (3) | H42A—C42—H42B | 108.3 |
O3—C16—C17 | 108.4 (4) | O7—C43—C48 | 124.9 (4) |
O3—C16—H16A | 110.0 | O7—C43—C44 | 114.9 (3) |
C17—C16—H16A | 110.0 | C48—C43—C44 | 120.2 (4) |
O3—C16—H16B | 110.0 | C45—C44—C43 | 120.2 (4) |
C17—C16—H16B | 110.0 | C45—C44—H44 | 119.9 |
H16A—C16—H16B | 108.4 | C43—C44—H44 | 119.9 |
C16—C17—H17A | 109.5 | C44—C45—C46 | 120.4 (4) |
C16—C17—H17B | 109.5 | C44—C45—H45 | 119.8 |
H17A—C17—H17B | 109.5 | C46—C45—H45 | 119.8 |
C16—C17—H17C | 109.5 | C47—C46—C45 | 118.7 (4) |
H17A—C17—H17C | 109.5 | C47—C46—C49 | 119.1 (4) |
H17B—C17—H17C | 109.5 | C45—C46—C49 | 122.2 (4) |
C23—C18—C19 | 118.9 (4) | C46—C47—C48 | 121.3 (3) |
C23—C18—C25 | 120.5 (4) | C46—C47—H47 | 119.3 |
C19—C18—C25 | 120.6 (3) | C48—C47—H47 | 119.3 |
C18—C19—C20 | 120.2 (4) | C43—C48—C47 | 119.1 (4) |
C18—C19—H19 | 119.9 | C43—C48—H48 | 120.4 |
C20—C19—H19 | 119.9 | C47—C48—H48 | 120.4 |
C21—C20—C19 | 120.9 (4) | O8—C49—O9 | 120.3 (4) |
C21—C20—H20 | 119.5 | O8—C49—O9B | 122.3 (6) |
C19—C20—H20 | 119.5 | O8—C49—C46 | 125.2 (4) |
C22—C21—C20 | 118.4 (4) | O9—C49—C46 | 113.9 (4) |
C22—C21—C24 | 120.7 (4) | O9B—C49—C46 | 102.7 (5) |
C20—C21—C24 | 120.9 (4) | C49—O9—C50 | 120.1 (5) |
C21—C22—C23 | 120.9 (4) | O9—C50—C51 | 110.1 (7) |
C21—C22—H22 | 119.5 | O9—C50—H50A | 109.6 |
C23—C22—H22 | 119.5 | C51—C50—H50A | 109.6 |
C18—C23—C22 | 120.7 (4) | O9—C50—H50B | 109.6 |
C18—C23—H23 | 119.7 | C51—C50—H50B | 109.6 |
C22—C23—H23 | 119.7 | H50A—C50—H50B | 108.2 |
C21—C24—H24A | 109.5 | C50—C51—H51A | 109.5 |
C21—C24—H24B | 109.5 | C50—C51—H51B | 109.5 |
H24A—C24—H24B | 109.5 | H51A—C51—H51B | 109.5 |
C21—C24—H24C | 109.5 | C50—C51—H51C | 109.5 |
H24A—C24—H24C | 109.5 | H51A—C51—H51C | 109.5 |
H24B—C24—H24C | 109.5 | H51B—C51—H51C | 109.5 |
O4—C25—C18 | 107.9 (3) | C49—O9B—C50B | 111.7 (11) |
O4—C25—H25A | 110.1 | O9B—C50B—C51B | 109 (2) |
C18—C25—H25A | 110.1 | O9B—C50B—H50C | 109.9 |
O4—C25—H25B | 110.1 | C51B—C50B—H50C | 109.9 |
C18—C25—H25B | 110.1 | O9B—C50B—H50D | 109.9 |
H25A—C25—H25B | 108.4 | C51B—C50B—H50D | 109.9 |
O4—C26—C31 | 124.7 (3) | H50C—C50B—H50D | 108.3 |
O4—C26—C27 | 114.9 (3) | C50B—C51B—H51D | 109.5 |
C31—C26—C27 | 120.3 (4) | C50B—C51B—H51E | 109.5 |
C28—C27—C26 | 119.6 (3) | H51D—C51B—H51E | 109.5 |
C28—C27—H27 | 120.2 | C50B—C51B—H51F | 109.5 |
C26—C27—H27 | 120.2 | H51D—C51B—H51F | 109.5 |
C27—C28—C29 | 120.7 (4) | H51E—C51B—H51F | 109.5 |
C6—C1—C2—C3 | 0.4 (6) | C27—C28—C29—C32 | −176.7 (3) |
C8—C1—C2—C3 | −175.3 (4) | C28—C29—C30—C31 | −1.3 (5) |
C1—C2—C3—C4 | −1.1 (6) | C32—C29—C30—C31 | 177.0 (4) |
C2—C3—C4—C5 | 0.3 (6) | O4—C26—C31—C30 | −178.7 (3) |
C2—C3—C4—C7 | −177.6 (4) | C27—C26—C31—C30 | 3.1 (6) |
C3—C4—C5—C6 | 1.2 (6) | C29—C30—C31—C26 | −1.0 (6) |
C7—C4—C5—C6 | 179.1 (4) | C33—O6—C32—O5 | 4.1 (6) |
C2—C1—C6—C5 | 1.2 (6) | C33—O6—C32—C29 | −175.2 (4) |
C8—C1—C6—C5 | 176.7 (4) | C30—C29—C32—O5 | −177.3 (4) |
C4—C5—C6—C1 | −2.0 (6) | C28—C29—C32—O5 | 1.0 (6) |
C9—O1—C8—C1 | −174.9 (3) | C30—C29—C32—O6 | 2.0 (5) |
C6—C1—C8—O1 | 40.1 (5) | C28—C29—C32—O6 | −179.6 (4) |
C2—C1—C8—O1 | −144.3 (4) | C32—O6—C33—C34 | 81.8 (5) |
C8—O1—C9—C10 | −174.1 (4) | C40—C35—C36—C37 | 2.2 (6) |
C8—O1—C9—C14 | 7.1 (6) | C42—C35—C36—C37 | −177.5 (4) |
O1—C9—C10—C11 | −178.7 (4) | C35—C36—C37—C38 | −1.6 (7) |
C14—C9—C10—C11 | 0.1 (6) | C36—C37—C38—C39 | −0.1 (7) |
C9—C10—C11—C12 | −0.4 (7) | C36—C37—C38—C41 | 178.3 (4) |
C10—C11—C12—C13 | 0.6 (7) | C37—C38—C39—C40 | 1.1 (7) |
C10—C11—C12—C15 | −179.5 (4) | C41—C38—C39—C40 | −177.3 (4) |
C11—C12—C13—C14 | −0.5 (6) | C36—C35—C40—C39 | −1.1 (6) |
C15—C12—C13—C14 | 179.6 (4) | C42—C35—C40—C39 | 178.6 (4) |
O1—C9—C14—C13 | 178.8 (4) | C38—C39—C40—C35 | −0.5 (7) |
C10—C9—C14—C13 | 0.0 (6) | C43—O7—C42—C35 | 173.7 (3) |
C12—C13—C14—C9 | 0.2 (6) | C36—C35—C42—O7 | −118.9 (4) |
C16—O3—C15—O2 | 1.5 (7) | C40—C35—C42—O7 | 61.4 (5) |
C16—O3—C15—C12 | −175.5 (4) | C42—O7—C43—C48 | 2.1 (5) |
C13—C12—C15—O2 | 173.9 (5) | C42—O7—C43—C44 | −177.2 (3) |
C11—C12—C15—O2 | −6.0 (7) | O7—C43—C44—C45 | 177.6 (3) |
C13—C12—C15—O3 | −9.3 (6) | C48—C43—C44—C45 | −1.6 (6) |
C11—C12—C15—O3 | 170.9 (4) | C43—C44—C45—C46 | 1.2 (6) |
C15—O3—C16—C17 | 173.7 (5) | C44—C45—C46—C47 | 0.8 (6) |
C23—C18—C19—C20 | −1.3 (6) | C44—C45—C46—C49 | −179.1 (4) |
C25—C18—C19—C20 | 179.4 (4) | C45—C46—C47—C48 | −2.2 (6) |
C18—C19—C20—C21 | 1.0 (7) | C49—C46—C47—C48 | 177.6 (4) |
C19—C20—C21—C22 | 0.4 (7) | O7—C43—C48—C47 | −179.0 (3) |
C19—C20—C21—C24 | −178.9 (4) | C44—C43—C48—C47 | 0.2 (5) |
C20—C21—C22—C23 | −1.6 (7) | C46—C47—C48—C43 | 1.8 (5) |
C24—C21—C22—C23 | 177.7 (4) | C47—C46—C49—O8 | 21.5 (6) |
C19—C18—C23—C22 | 0.1 (6) | C45—C46—C49—O8 | −158.6 (4) |
C25—C18—C23—C22 | 179.4 (4) | C47—C46—C49—O9 | −149.8 (4) |
C21—C22—C23—C18 | 1.4 (7) | C45—C46—C49—O9 | 30.1 (6) |
C26—O4—C25—C18 | 178.3 (3) | C47—C46—C49—O9B | 167.6 (7) |
C23—C18—C25—O4 | −70.6 (5) | C45—C46—C49—O9B | −12.5 (8) |
C19—C18—C25—O4 | 108.7 (4) | O8—C49—O9—C50 | 6.4 (8) |
C25—O4—C26—C31 | 1.6 (5) | C46—C49—O9—C50 | 178.2 (5) |
C25—O4—C26—C27 | 180.0 (3) | C49—O9—C50—C51 | 82.8 (8) |
O4—C26—C27—C28 | 178.8 (3) | O8—C49—O9B—C50B | −24.0 (16) |
C31—C26—C27—C28 | −2.7 (6) | C46—C49—O9B—C50B | −171.4 (12) |
C26—C27—C28—C29 | 0.3 (6) | C49—O9B—C50B—C51B | −66 (2) |
C27—C28—C29—C30 | 1.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C42—H42A···O8i | 0.99 | 2.65 | 3.269 (5) | 121 |
C44—H44···O4 | 0.95 | 2.66 | 3.374 (5) | 133 |
Symmetry code: (i) −x+1, y+1/2, −z+2. |
C—H···π = angle of the X—H bond with the π-plane (perpendicular = 90°, parallel = 0°). Ring Cg1 = C35–C40; Cg2 = C43–C48; Cg3 = C1–C6; Cg4 = C9–C14; Cg6 = C26–C31 |
C—H | Cg(J) | Symmetry code (J) | H···Cg | C—H···Cg | C···Cg | C—H···π |
C8—H8A | Cg3 | -x, 1/2 + y, -z | 2.90 | 144 | 3.749 (5) | 59 |
C20—H20 | Cg1 | x, y, z | 2.81 | 147 | 3.653 (6) | 62 |
C22—H22 | Cg4 | x, 1 + y, 1 + z | 2.93 | 137 | 3.688 (6) | 50 |
C25—H25A | Cg2 | x, 1 + y, z | 2.81 | 143 | 3.654 (6) | 50 |
C41—H41B | Cg1 | 1 - x, 1/2 + y, 3 - z | 2.67 | 156 | 3.590 (5) | 75 |
C45—H45 | Cg6 | x, y, z | 2.82 | 147 | 3.654 (4) | 51 |
C47—H47 | Cg2 | 1 - x, -1/2 + y, 2 - z | 2.77 | 148 | 3.615 (4) | 65 |
Acknowledgements
The authors are grateful to the Department of Chemistry, University of Rajshahi for laboratory facilities. MCS thanks the Department of Applied Chemistry, Faculty of Engineering, University of Toyama for analytical facilities.
Funding information
Funding for this research was provided by: University Grants Commission Bangladesh.
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