research communications
S,8aR)-3,5a-dimethyl-8-methylidene-2-oxododecahydrooxireno[2′,3′:6,7]naphtho[1,2-b]furan-6-yl (Z)-2-methylbut-2-enoate extracted from Ferula persica
and Hirshfeld surface analysis of (5aaAzerbaijan Medical University, Bakikhanov st. 23, AZ1022, Baku, Azerbaijan, bPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation, cN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, e"Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan, fDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan, and gDepartment of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal
*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np
In the title compound, C20H26O5, the two cyclohexane rings adopt boat and half-chair conformations. In the crystal, adjacent molecules are connected by intermolecular C—H⋯O hydrogen bonds, forming a three-dimensional network. According to a Hirshfeld surface study, H⋯H interactions are the most significant contributors to the crystal packing (63.0%).
Keywords: crystal structure; hydrogen bonds; sesquiterpene lactones; Ferula persica; Hirshfeld surface analysis.
CCDC reference: 2255517
1. Chemical context
Sesquiterpene Ferula genus is rich in specifically sesquiterpene Ferula species are found in the Mediterranean region, Central Asia, Siberia, China, Afghanistan, Iran, North Africa and the Caucasus (Mir-Babayev & Houghton, 2002). The members of this genus typically have a heavy fragrance due to the presence of essential oils or oleoresins in their content. This genus is applied for the cure of various organ disorders in folk medicine (Salehi et al., 2019). These herbs have been used for oleo-gum resin, plant extracts, and essential oils. Moreover, the essential oils and extracts of different species of this herb can be used as natural food preservatives due to their antioxidant and antimicrobial activity (Daneshniya et al., 2021).
are a significant group of natural products isolated from the extracts of various parts of medicinal plants. As a medicinal plant, theHerein, in the framework of our ongoing structural studies, we report the S,8aR)-3,5a-dimethyl-8-methylidene-2-oxododecahydrooxireno[2′,3′:6,7]naphtho[1,2-b]furan-6-yl (Z)-2-methylbut-2-enoate extracted from Ferula persica.
and Hirshfeld surface analysis of the title compound, (5a2. Structural commentary
A view of the molecular structure of the title compound is shown in Fig. 1. The cyclohexane rings (A: C3A/C4/C5/C5A/C9A/C9B; B: C5A/C6–C9/C9A) adopt boat and half-chair conformations, respectively. The puckering parameters (Cremer & Pople, 1975) of the A and B rings are QT = 0.7259 (19) Å, θ = 83.29 (15)°, φ = 51.45 (15)°, and QT = 0.5337 (18) Å, θ = 52.1 (2)°, φ = 331.7 (3)°, respectively.
3. Supramolecular features and Hirshfeld surface analysis
In the crystal of the title compound, adjacent molecules are connected by intermolecular C—H⋯O hydrogen bonds, forming a three dimensional network (Tables 1 and 2). Figs. 2, 3 and 4 show packing views of the title compound down the a, b and c axes, respectively.
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CrystalExplorer17 (Spackman et al., 2021) was used to compute Hirshfeld surfaces of the title molecule. The dnorm mappings for the molecule were performed in the range −0.1633 to +1.3364 a.u. The locations of the C—H⋯O interactions are shown by intense red circles on the dnorm surface (Fig. 5a,b).
Fig. 6 shows the full two-dimensional fingerprint plots for the molecule and those delineated into the major contacts. H⋯H interactions (Fig. 6b; 63.0% contribution) are the major contributor to the crystal packing with O⋯H/H⋯O (Fig. 6c; 28.3%) and C⋯H/H⋯C (Fig. 6d; 7.5%) interactions representing the next highest contributions. The percentage contributions of comparatively weaker interactions are O⋯C/C⋯O (0.5%) , O⋯O (0.4%) and C⋯C (0.3%). Relevant short intermolecular atomic contacts are summarized in Table 2.
4. Database survey
Two closely related compounds are 1β-angeloyloxy-2β,3β-epoxy-5βH,7αH-l0α-methyleudesma-4(15),11(13)-dien-6,12-olide (I) (Rychlewska et al., 1992) and 1β-angeloyloxy-5βH,6αH,7αH,11αH-10α-methyleudesma-2,4(15)-dien-6,12-olide (II) (Rychlewska et al., 1992).
The largest difference between the two structures (I and II) lies in the cyclohexane B ring, which is of the rigid-chair type in I and of the flexible boat type in II. In both crystal structures, the molecules are held together mostly by van der Waals forces.
5. Synthesis and crystallization
The title compound has previously been isolated from the roots of the Ferula oopoda plant and fully characterized (Serkerov, 1972). The compound used for the current study was isolated from the roots of the Ferula persica herb by a similar method.
6. Refinement
Crystal data, data collection and structure . H atoms of the –C=CH2 group were located in a difference-Fourier map and refined freely [C17—H17A = 0.94 (2) Å, C17—H17B = 0.97 (2) Å]. All other H atoms were placed at calculated positions and refined using a riding model, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C). The remaining maximum electron density peak (0.56 e− Å−3) is 1.41 Å away from C17 and the minimum density peak (–0.16 e Å−3) is 0.92 Å away from C9.
details are summarized in Table 3Supporting information
CCDC reference: 2255517
https://doi.org/10.1107/S205698902300333X/wm5679sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902300333X/wm5679Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2022); cell
CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).C20H26O5 | Dx = 1.305 Mg m−3 |
Mr = 346.41 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 16716 reflections |
a = 7.11296 (5) Å | θ = 3.9–77.3° |
b = 15.4597 (10) Å | µ = 0.76 mm−1 |
c = 16.0358 (10) Å | T = 100 K |
V = 1763.36 (16) Å3 | Prism, yellow |
Z = 4 | 0.21 × 0.18 × 0.13 mm |
F(000) = 744 |
XtaLAB Synergy, Dualflex, HyPix diffractometer | 3717 reflections with I > 2σ(I) |
Radiation source: micro-focus sealed X-ray tube | Rint = 0.024 |
φ and ω scans | θmax = 77.8°, θmin = 4.0° |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2022) | h = −9→8 |
Tmin = 0.674, Tmax = 1.000 | k = −19→16 |
19755 measured reflections | l = −18→20 |
3751 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.4585P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3751 reflections | Δρmax = 0.56 e Å−3 |
238 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al, 2013). |
Primary atom site location: difference Fourier map | Absolute structure parameter: 0.01 (4) |
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 | ||
O1 | 0.27214 (18) | 0.55551 (9) | 0.81184 (8) | 0.0258 (3) | |
O2 | 0.1708 (2) | 0.66397 (9) | 0.89164 (9) | 0.0325 (3) | |
O3 | 0.62078 (17) | 0.61814 (8) | 0.55679 (8) | 0.0217 (3) | |
O4 | 0.7139 (2) | 0.60760 (8) | 0.42338 (8) | 0.0316 (3) | |
C2 | 0.2969 (3) | 0.61638 (12) | 0.87107 (10) | 0.0257 (4) | |
C3 | 0.4949 (3) | 0.61151 (12) | 0.90431 (11) | 0.0278 (4) | |
H3 | 0.4936 | 0.5693 | 0.9516 | 0.033* | |
C3A | 0.6045 (3) | 0.56914 (11) | 0.83285 (11) | 0.0237 (4) | |
H3A | 0.7026 | 0.5300 | 0.8568 | 0.028* | |
C4 | 0.6965 (3) | 0.62980 (11) | 0.76998 (11) | 0.0259 (4) | |
H4A | 0.7893 | 0.6675 | 0.7983 | 0.031* | |
H4B | 0.6003 | 0.6670 | 0.7434 | 0.031* | |
C5 | 0.7941 (3) | 0.57422 (12) | 0.70428 (12) | 0.0270 (4) | |
H5A | 0.8994 | 0.5429 | 0.7311 | 0.032* | |
H5B | 0.8483 | 0.6127 | 0.6612 | 0.032* | |
C5A | 0.6636 (2) | 0.50725 (11) | 0.66081 (11) | 0.0220 (3) | |
C6 | 0.6543 (3) | 0.52614 (11) | 0.56680 (11) | 0.0226 (3) | |
H6 | 0.7798 | 0.5124 | 0.5420 | 0.027* | |
C7 | 0.5062 (3) | 0.47385 (11) | 0.52056 (11) | 0.0234 (4) | |
H7 | 0.5477 | 0.4454 | 0.4677 | 0.028* | |
C8 | 0.3552 (3) | 0.42987 (11) | 0.56746 (11) | 0.0227 (3) | |
H8 | 0.3055 | 0.3750 | 0.5428 | 0.027* | |
C9 | 0.3431 (2) | 0.43826 (11) | 0.65931 (11) | 0.0217 (3) | |
C9A | 0.4598 (2) | 0.51073 (10) | 0.69607 (10) | 0.0194 (3) | |
H9A | 0.4033 | 0.5660 | 0.6756 | 0.023* | |
C9B | 0.4515 (2) | 0.51404 (11) | 0.79115 (10) | 0.0219 (3) | |
H9B | 0.4543 | 0.4540 | 0.8143 | 0.026* | |
O10 | 0.31873 (19) | 0.50878 (8) | 0.52107 (8) | 0.0254 (3) | |
C10 | 0.5680 (4) | 0.69679 (14) | 0.93885 (14) | 0.0379 (5) | |
H10A | 0.5624 | 0.7412 | 0.8953 | 0.057* | |
H10B | 0.6984 | 0.6895 | 0.9572 | 0.057* | |
H10C | 0.4902 | 0.7146 | 0.9863 | 0.057* | |
C11 | 0.7473 (3) | 0.41612 (12) | 0.67128 (13) | 0.0295 (4) | |
H11A | 0.7450 | 0.3999 | 0.7303 | 0.044* | |
H11B | 0.8774 | 0.4159 | 0.6511 | 0.044* | |
H11C | 0.6729 | 0.3746 | 0.6390 | 0.044* | |
C12 | 0.6677 (3) | 0.65206 (11) | 0.48211 (11) | 0.0214 (3) | |
C13 | 0.6622 (2) | 0.74835 (11) | 0.48349 (10) | 0.0201 (3) | |
C14 | 0.6640 (2) | 0.79339 (11) | 0.41196 (11) | 0.0215 (3) | |
H14 | 0.6658 | 0.8546 | 0.4177 | 0.026* | |
C15 | 0.6619 (3) | 0.79287 (11) | 0.56742 (11) | 0.0224 (3) | |
H15A | 0.5441 | 0.7800 | 0.5966 | 0.034* | |
H15B | 0.6732 | 0.8555 | 0.5594 | 0.034* | |
H15C | 0.7682 | 0.7720 | 0.6007 | 0.034* | |
C16 | 0.6635 (3) | 0.75991 (11) | 0.32443 (11) | 0.0245 (4) | |
H16A | 0.6156 | 0.8048 | 0.2868 | 0.037* | |
H16B | 0.5826 | 0.7087 | 0.3210 | 0.037* | |
H16C | 0.7918 | 0.7443 | 0.3081 | 0.037* | |
C17 | 0.2362 (3) | 0.38217 (12) | 0.70195 (12) | 0.0251 (4) | |
H17A | 0.165 (3) | 0.3387 (14) | 0.6752 (13) | 0.018 (5)* | |
H17B | 0.218 (3) | 0.3870 (14) | 0.7618 (15) | 0.028 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0248 (6) | 0.0325 (6) | 0.0203 (6) | −0.0019 (5) | 0.0003 (5) | −0.0013 (5) |
O2 | 0.0399 (8) | 0.0341 (7) | 0.0234 (6) | 0.0069 (6) | 0.0046 (6) | 0.0021 (5) |
O3 | 0.0268 (6) | 0.0167 (5) | 0.0218 (6) | 0.0001 (5) | 0.0052 (5) | 0.0007 (5) |
O4 | 0.0485 (8) | 0.0216 (6) | 0.0247 (6) | −0.0013 (6) | 0.0106 (6) | −0.0019 (5) |
C2 | 0.0347 (10) | 0.0268 (8) | 0.0156 (7) | −0.0025 (8) | 0.0019 (7) | 0.0039 (6) |
C3 | 0.0355 (10) | 0.0264 (9) | 0.0214 (8) | −0.0034 (8) | −0.0035 (8) | 0.0013 (7) |
C3A | 0.0269 (9) | 0.0224 (8) | 0.0219 (8) | −0.0020 (7) | −0.0054 (7) | 0.0025 (7) |
C4 | 0.0273 (9) | 0.0230 (8) | 0.0275 (9) | −0.0057 (7) | −0.0051 (7) | 0.0015 (7) |
C5 | 0.0221 (8) | 0.0304 (9) | 0.0286 (9) | −0.0043 (7) | −0.0033 (7) | 0.0025 (7) |
C5A | 0.0206 (8) | 0.0205 (8) | 0.0251 (8) | 0.0016 (6) | −0.0003 (7) | 0.0015 (6) |
C6 | 0.0248 (8) | 0.0169 (7) | 0.0261 (8) | 0.0022 (6) | 0.0045 (7) | 0.0012 (7) |
C7 | 0.0322 (9) | 0.0173 (7) | 0.0209 (8) | 0.0030 (7) | 0.0016 (7) | 0.0002 (6) |
C8 | 0.0279 (8) | 0.0170 (7) | 0.0231 (8) | 0.0015 (6) | −0.0018 (7) | 0.0004 (6) |
C9 | 0.0216 (8) | 0.0207 (8) | 0.0230 (8) | 0.0005 (7) | −0.0013 (7) | −0.0001 (6) |
C9A | 0.0211 (8) | 0.0184 (7) | 0.0188 (7) | 0.0001 (6) | −0.0010 (6) | 0.0019 (6) |
C9B | 0.0251 (9) | 0.0206 (8) | 0.0199 (8) | −0.0018 (7) | −0.0019 (6) | 0.0027 (6) |
O10 | 0.0308 (7) | 0.0197 (6) | 0.0258 (6) | 0.0008 (5) | −0.0053 (5) | 0.0020 (5) |
C10 | 0.0463 (12) | 0.0327 (10) | 0.0348 (11) | −0.0077 (9) | 0.0000 (10) | −0.0097 (9) |
C11 | 0.0271 (9) | 0.0261 (9) | 0.0355 (10) | 0.0064 (7) | −0.0023 (8) | 0.0062 (8) |
C12 | 0.0230 (8) | 0.0204 (8) | 0.0208 (8) | −0.0017 (7) | 0.0022 (7) | −0.0003 (6) |
C13 | 0.0183 (7) | 0.0195 (7) | 0.0225 (8) | −0.0017 (6) | 0.0016 (7) | −0.0004 (6) |
C14 | 0.0196 (8) | 0.0200 (7) | 0.0248 (8) | −0.0011 (6) | 0.0004 (7) | −0.0002 (6) |
C15 | 0.0239 (8) | 0.0203 (7) | 0.0230 (8) | −0.0013 (7) | 0.0010 (7) | −0.0016 (6) |
C16 | 0.0261 (9) | 0.0261 (8) | 0.0212 (8) | 0.0014 (7) | 0.0011 (7) | 0.0007 (7) |
C17 | 0.0234 (8) | 0.0258 (8) | 0.0262 (9) | −0.0036 (7) | −0.0017 (7) | −0.0006 (7) |
O1—C2 | 1.349 (2) | C8—O10 | 1.452 (2) |
O1—C9B | 1.466 (2) | C8—C9 | 1.481 (2) |
O2—C2 | 1.206 (2) | C8—H8 | 1.0000 |
O3—C12 | 1.349 (2) | C9—C17 | 1.341 (3) |
O3—C6 | 1.4510 (19) | C9—C9A | 1.514 (2) |
O4—C12 | 1.211 (2) | C9A—C9B | 1.527 (2) |
C2—C3 | 1.508 (3) | C9A—H9A | 1.0000 |
C3—C10 | 1.522 (3) | C9B—H9B | 1.0000 |
C3—C3A | 1.533 (3) | C10—H10A | 0.9800 |
C3—H3 | 1.0000 | C10—H10B | 0.9800 |
C3A—C4 | 1.525 (2) | C10—H10C | 0.9800 |
C3A—C9B | 1.535 (2) | C11—H11A | 0.9800 |
C3A—H3A | 1.0000 | C11—H11B | 0.9800 |
C4—C5 | 1.526 (3) | C11—H11C | 0.9800 |
C4—H4A | 0.9900 | C12—C13 | 1.489 (2) |
C4—H4B | 0.9900 | C13—C14 | 1.342 (2) |
C5—C5A | 1.556 (2) | C13—C15 | 1.512 (2) |
C5—H5A | 0.9900 | C14—C16 | 1.496 (2) |
C5—H5B | 0.9900 | C14—H14 | 0.9500 |
C5A—C6 | 1.537 (2) | C15—H15A | 0.9800 |
C5A—C11 | 1.539 (2) | C15—H15B | 0.9800 |
C5A—C9A | 1.557 (2) | C15—H15C | 0.9800 |
C6—C7 | 1.521 (3) | C16—H16A | 0.9800 |
C6—H6 | 1.0000 | C16—H16B | 0.9800 |
C7—O10 | 1.439 (2) | C16—H16C | 0.9800 |
C7—C8 | 1.477 (3) | C17—H17A | 0.94 (2) |
C7—H7 | 1.0000 | C17—H17B | 0.97 (2) |
C2—O1—C9B | 110.55 (14) | C17—C9—C8 | 118.92 (16) |
C12—O3—C6 | 116.01 (13) | C17—C9—C9A | 126.23 (16) |
O2—C2—O1 | 121.42 (18) | C8—C9—C9A | 114.83 (15) |
O2—C2—C3 | 128.94 (17) | C9—C9A—C9B | 113.11 (14) |
O1—C2—C3 | 109.64 (16) | C9—C9A—C5A | 110.09 (14) |
C2—C3—C10 | 113.86 (17) | C9B—C9A—C5A | 113.57 (14) |
C2—C3—C3A | 103.43 (14) | C9—C9A—H9A | 106.5 |
C10—C3—C3A | 117.94 (17) | C9B—C9A—H9A | 106.5 |
C2—C3—H3 | 107.0 | C5A—C9A—H9A | 106.5 |
C10—C3—H3 | 107.0 | O1—C9B—C9A | 105.92 (13) |
C3A—C3—H3 | 107.0 | O1—C9B—C3A | 106.01 (13) |
C4—C3A—C3 | 116.74 (15) | C9A—C9B—C3A | 115.22 (14) |
C4—C3A—C9B | 110.96 (14) | O1—C9B—H9B | 109.8 |
C3—C3A—C9B | 101.65 (15) | C9A—C9B—H9B | 109.8 |
C4—C3A—H3A | 109.0 | C3A—C9B—H9B | 109.8 |
C3—C3A—H3A | 109.0 | C7—O10—C8 | 61.44 (11) |
C9B—C3A—H3A | 109.0 | C3—C10—H10A | 109.5 |
C3A—C4—C5 | 107.78 (15) | C3—C10—H10B | 109.5 |
C3A—C4—H4A | 110.2 | H10A—C10—H10B | 109.5 |
C5—C4—H4A | 110.2 | C3—C10—H10C | 109.5 |
C3A—C4—H4B | 110.2 | H10A—C10—H10C | 109.5 |
C5—C4—H4B | 110.2 | H10B—C10—H10C | 109.5 |
H4A—C4—H4B | 108.5 | C5A—C11—H11A | 109.5 |
C4—C5—C5A | 114.37 (16) | C5A—C11—H11B | 109.5 |
C4—C5—H5A | 108.7 | H11A—C11—H11B | 109.5 |
C5A—C5—H5A | 108.7 | C5A—C11—H11C | 109.5 |
C4—C5—H5B | 108.7 | H11A—C11—H11C | 109.5 |
C5A—C5—H5B | 108.7 | H11B—C11—H11C | 109.5 |
H5A—C5—H5B | 107.6 | O4—C12—O3 | 122.45 (16) |
C6—C5A—C11 | 107.32 (15) | O4—C12—C13 | 125.87 (16) |
C6—C5A—C5 | 109.79 (14) | O3—C12—C13 | 111.64 (14) |
C11—C5A—C5 | 109.24 (15) | C14—C13—C12 | 120.38 (15) |
C6—C5A—C9A | 108.03 (14) | C14—C13—C15 | 121.65 (15) |
C11—C5A—C9A | 110.64 (14) | C12—C13—C15 | 117.93 (15) |
C5—C5A—C9A | 111.71 (14) | C13—C14—C16 | 128.49 (15) |
O3—C6—C7 | 110.69 (14) | C13—C14—H14 | 115.8 |
O3—C6—C5A | 107.57 (13) | C16—C14—H14 | 115.8 |
C7—C6—C5A | 114.02 (14) | C13—C15—H15A | 109.5 |
O3—C6—H6 | 108.1 | C13—C15—H15B | 109.5 |
C7—C6—H6 | 108.1 | H15A—C15—H15B | 109.5 |
C5A—C6—H6 | 108.1 | C13—C15—H15C | 109.5 |
O10—C7—C8 | 59.73 (11) | H15A—C15—H15C | 109.5 |
O10—C7—C6 | 116.08 (13) | H15B—C15—H15C | 109.5 |
C8—C7—C6 | 120.00 (15) | C14—C16—H16A | 109.5 |
O10—C7—H7 | 116.3 | C14—C16—H16B | 109.5 |
C8—C7—H7 | 116.3 | H16A—C16—H16B | 109.5 |
C6—C7—H7 | 116.3 | C14—C16—H16C | 109.5 |
O10—C8—C7 | 58.83 (11) | H16A—C16—H16C | 109.5 |
O10—C8—C9 | 115.17 (14) | H16B—C16—H16C | 109.5 |
C7—C8—C9 | 120.57 (16) | C9—C17—H17A | 122.2 (13) |
O10—C8—H8 | 116.5 | C9—C17—H17B | 122.1 (14) |
C7—C8—H8 | 116.5 | H17A—C17—H17B | 115.5 (19) |
C9—C8—H8 | 116.5 | ||
C9B—O1—C2—O2 | 172.91 (16) | O10—C8—C9—C9A | −52.2 (2) |
C9B—O1—C2—C3 | −8.26 (18) | C7—C8—C9—C9A | 15.0 (2) |
O2—C2—C3—C10 | −28.0 (3) | C17—C9—C9A—C9B | 1.8 (3) |
O1—C2—C3—C10 | 153.32 (16) | C8—C9—C9A—C9B | −176.92 (15) |
O2—C2—C3—C3A | −157.18 (18) | C17—C9—C9A—C5A | 130.09 (19) |
O1—C2—C3—C3A | 24.10 (18) | C8—C9—C9A—C5A | −48.67 (19) |
C2—C3—C3A—C4 | 92.11 (18) | C6—C5A—C9A—C9 | 65.44 (17) |
C10—C3—C3A—C4 | −34.6 (2) | C11—C5A—C9A—C9 | −51.76 (19) |
C2—C3—C3A—C9B | −28.74 (17) | C5—C5A—C9A—C9 | −173.70 (14) |
C10—C3—C3A—C9B | −155.42 (17) | C6—C5A—C9A—C9B | −166.57 (14) |
C3—C3A—C4—C5 | −179.07 (15) | C11—C5A—C9A—C9B | 76.22 (19) |
C9B—C3A—C4—C5 | −63.29 (19) | C5—C5A—C9A—C9B | −45.71 (19) |
C3A—C4—C5—C5A | 55.2 (2) | C2—O1—C9B—C9A | −133.99 (14) |
C4—C5—C5A—C6 | 118.63 (17) | C2—O1—C9B—C3A | −11.12 (17) |
C4—C5—C5A—C11 | −123.94 (17) | C9—C9A—C9B—O1 | −78.72 (17) |
C4—C5—C5A—C9A | −1.2 (2) | C5A—C9A—C9B—O1 | 154.87 (13) |
C12—O3—C6—C7 | −75.56 (18) | C9—C9A—C9B—C3A | 164.45 (14) |
C12—O3—C6—C5A | 159.27 (14) | C5A—C9A—C9B—C3A | 38.0 (2) |
C11—C5A—C6—O3 | −166.03 (14) | C4—C3A—C9B—O1 | −99.98 (16) |
C5—C5A—C6—O3 | −47.40 (18) | C3—C3A—C9B—O1 | 24.83 (16) |
C9A—C5A—C6—O3 | 74.64 (17) | C4—C3A—C9B—C9A | 16.8 (2) |
C11—C5A—C6—C7 | 70.81 (18) | C3—C3A—C9B—C9A | 141.61 (15) |
C5—C5A—C6—C7 | −170.56 (14) | C6—C7—O10—C8 | −111.03 (17) |
C9A—C5A—C6—C7 | −48.52 (18) | C9—C8—O10—C7 | 111.87 (18) |
O3—C6—C7—O10 | −36.6 (2) | C6—O3—C12—O4 | 8.5 (3) |
C5A—C6—C7—O10 | 84.87 (18) | C6—O3—C12—C13 | −169.25 (15) |
O3—C6—C7—C8 | −105.14 (17) | O4—C12—C13—C14 | 16.9 (3) |
C5A—C6—C7—C8 | 16.3 (2) | O3—C12—C13—C14 | −165.42 (16) |
C6—C7—C8—O10 | 104.52 (16) | O4—C12—C13—C15 | −160.91 (18) |
O10—C7—C8—C9 | −102.71 (17) | O3—C12—C13—C15 | 16.8 (2) |
C6—C7—C8—C9 | 1.8 (2) | C12—C13—C14—C16 | 2.7 (3) |
O10—C8—C9—C17 | 128.89 (18) | C15—C13—C14—C16 | −179.63 (18) |
C7—C8—C9—C17 | −163.85 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···O4i | 1.00 | 2.45 | 3.353 (2) | 149 |
C5—H5B···O3 | 0.99 | 2.33 | 2.752 (2) | 105 |
C8—H8···O2ii | 1.00 | 2.50 | 3.176 (2) | 124 |
C9A—H9A···O3 | 1.00 | 2.58 | 3.010 (2) | 106 |
C14—H14···O10iii | 0.95 | 2.57 | 3.423 (2) | 149 |
C16—H16B···O4 | 0.98 | 2.45 | 2.862 (2) | 105 |
Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z−1/2; (iii) x+1/2, −y+3/2, −z+1. |
H15A···H16C | 2.39 | -1/2 + x, 3/2 - y, 1 - z |
O2···H8 | 2.50 | 1/2 - x, 1 - y, 1/2 + z |
O4···H3A | 2.45 | 3/2 - x, 1 - y, -1/2 + z |
H8···H10A | 2.48 | 1 - x, -1/2 + y, 3/2 - z |
H11B···H17A | 2.40 | 1 + x, y, z |
Acknowledgements
Authors' contributions are as follows. Conceptualization, ANK and IGM; methodology, ANK, EGK and IGM; investigation, ANK, MA and EGK; writing (original draft), MA and ANK; writing (review and editing of the manuscript), MA and ANK; visualization, MA, ANK and IGM; funding acquisition, VNK, AB and ANK; resources, AB, VNK and MNK; supervision, ANK and MA.
Funding information
This study was supported by Azerbaijan Medical University, Baku State University and the RUDN University Strategic Academic Leadership Program.
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