organic compounds
Ethyl (2RS,3SR,4RS)-1-ethyl-2-(furan-2-yl)-4-hydroxy-5-oxopyrrolidine-3-carboxylate
aFaculty of Applied Sciences, Universiti Teknologi MARA (UiTM) Pahang, Jengka Campus 26400, Bandar Tun Abdul Razak Jengka, Pahang, Malaysia, bCentre of Chemical Synthesis & Polymer Technology, Institute of Science, Universiti Teknologi MARA Puncak Alam, 42300 Puncak Alam, Selangor, Malaysia, cFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia, and dEaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, United Kingdom
*Correspondence e-mail: abdfatah@uitm.edu.my
The title racemic oxopyrrolidine compound, C13H17NO5, contains three stereogenic centres and crystallizes with two molecules in the The five-membered pyrrolidine rings in both molecules exhibit envelope conformations. The N-ethyl group of one of the molecules is disordered over two sets of sites in a 0.836 (4):0.164 (4) ratio. In the crystal, both molecules form inversion dimers through pairwise O—H⋯O hydrogen bonds, generating R22(10) loops, which are linked into a three-dimensional network by weak C—H⋯O hydrogen bonds.
Keywords: crystal structure; oxopyrrolidine; racemic; envelope conformation; hydrogen bonds.
CCDC reference: 2401488
Structure description
Pyrrolidine compounds have sparked interest as a motif in drug candidate molecules due to the non-planar ring structure and stereochemistry that allow for diverse spatial orientations of substituents, which can affect biological functions by altering binding affinity with the target protein (Petri et al., 2021). The versatility of these scaffolds is highlighted by their occurrences across a range of pharmacological uses, predominantly as antivirals, antidiabetics, and anticancer agents (Esposito et al., 2020; Wang et al., 2022). Hence, various strategies have been employed to obtain stereoselective reactions by exploiting the versatility of the pyrrolidine ring. For instance, a domino reaction of enynal and amino ketone with ZnCl2 followed by an aldol reaction yielded functionalized 2-furyl-pyrrolidine derivatives with high (Ou et al., 2023). Herein, we report a facile synthesis approach and of the title compound, C13H17NO5, as a continuation of our work to obtain pyrrolidine analogues with potential bioactivity.
The title compound, illustrated in Fig. 1, crystallizes in the monoclinic P21/n with two independent molecules in the each consisting of the five-membered pyrrolidine ring with furan, ethyl ester, and hydroxyl substituents at the 2, 3, and 4 ring positions, respectively. The stereogenic centres of each heterocycle have the relative stereochemistries RS, SR, RS at C2, C3, and C4, respectively. The core pyrrolidine rings in both molecules exhibit envelope conformations. Otherwise, the bond lengths and angles in the title compound agree well with similar pyrrolidine containing systems (e.g., Abdul Rashid et al., 2023).
In the extended structure of the title compound, both independent molecules form reciprocal O—H⋯O hydrogen bonded dimers with inversion-symmetry-related neighbours, in a R22(10) fashion, between the hydroxy and carbonyl substituents of the pyrrolidine ring. (Table 1, Fig. 2). These dimers then stack together, with independent molecules alternating, along [100] through non-classical C—H⋯O hydrogen bonds between adjacent furan moieties, which then further assemble into a three-dimensional network with support from non-classical hydrogen bonds between furan moieties and adjacent ester carbonyl O atoms.
Synthesis and crystallization
The 2-furyl-pyrrolecarboxylate precursor was synthesized using our published methods for related compounds (Mohammat et al., 2015) through the multiple-component reaction of sodium diethyl oxalacetate, furfural and ethylamine. The title compound was synthesized by adding acetic acid (0.28 ml, 3.83 mmol) followed by sodium borohydride (0.16 g, 4.21 mmol) to a stirred solution of 2-furyl-pyrrolecarboxylate (1.02 g, 3.83 mmol) in 20 ml dichloromethane at 0°C. The mixture was allowed to stir for 1 h at 0°C and a further 8 h at room temperature. The solvent was removed in vacuo and the crude product was dissolved in ethyl acetate and was extracted with water. The combined organic layers were washed with NaHCO3, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude product was subjected to using mixed eluents of ethyl acetate: hexane (1:1) (yield: 0.44 g, 43%). m.p. 259–260°C; FT—IR (ATR, ν, cm−1) 1733 (C=O), 1695 (C=O); 1H NMR (400 MHz, chloroform-d1) δ 7.39 (d, J = 1.9 Hz, 1H, HC=C), 6.38 (d, J = 3.0 Hz, 1H, HC=C) 6.32 (dd, J = 3.2, 1.8 Hz, 1H, HC=C), 4.75 (d, J = 8.5 Hz, 1H, NCH), 4.52 (d, J = 8.7 Hz, 1H, HCOH), 4.13 (m, J = 7.8, 6.7 Hz, 2H, OCH2), 3.46 (m, J = 14.6, 7.3 Hz, 1H, NCH2), 3.32 (t, J = 8.6 Hz, 1H, HCC=O), 2.73 (m, J = 14.2, 7.2 Hz, 1H, NCH2), 1.17 (t, J = 7.1 Hz, 3H, CH3), 0.89 (t, J = 7.3 Hz, 3H, CH3); 13C NMR (101 MHz, chloroform-d1) δ 171.73 (C=O), 171.08 (C=O), 149.17 (quat. C), 143.84 (HC=C), 110.83 (HC=C), 110.72 (HC=C), 72.29 (HCOH), 61.82 (CH2), 54.13 (NCH), 51.93 (HCC=O), 36.19 (NCH2), 14.18 (CH3), 12.43 (CH3); GC–MS: m/z [M+] = calculated for C13H17NO5: 267.11; found 267.1. Crystals suitable for X-ray diffraction studies were grown by slow evaporation of an ethyl acetate solution at room temperature.
Refinement
Crystal data, data collection and structure . The NEt group on one molecule (N21—C26—C27) is disordered over two orientations and was modelled with geometric and displacement-factor restraints on the minor component.
details are summarized in Table 2
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Structural data
CCDC reference: 2401488
https://doi.org/10.1107/S2414314624010885/hb4491sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624010885/hb4491Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314624010885/hb4491Isup3.cml
C13H17NO5 | F(000) = 1136 |
Mr = 267.27 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 11.15335 (7) Å | Cell parameters from 50600 reflections |
b = 17.41068 (9) Å | θ = 4.1–75.1° |
c = 14.06240 (9) Å | µ = 0.89 mm−1 |
β = 108.1547 (7)° | T = 100 K |
V = 2594.80 (3) Å3 | Prism, colourless |
Z = 8 | 0.14 × 0.07 × 0.03 mm |
Rigaku XtaLAB P200K diffractometer | 5344 independent reflections |
Radiation source: Rotating Anode, Rigaku MM-007HF | 4906 reflections with I > 2σ(I) |
Rigaku Osmic Confocal Optical System monochromator | Rint = 0.069 |
Detector resolution: 5.8140 pixels mm-1 | θmax = 75.5°, θmin = 4.2° |
shutterless scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2024) | k = −21→21 |
Tmin = 0.790, Tmax = 1.000 | l = −17→17 |
95957 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.0599P)2 + 0.6008P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
5344 reflections | Δρmax = 0.31 e Å−3 |
384 parameters | Δρmin = −0.20 e Å−3 |
22 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The O-bound H atoms were located in a difference map and refined isotropically with a distance restraint. The C-bound H atoms were located geometrically (C—H = 0.95–1.00 Å) and refined as riding atoms. The constraint Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C) was applied in all cases. The NEt group on one molecule (N21—C26—C27) was disordered over two positions and modelled with geometric and thermal restraints on minor component due to instability from low (<20%) occupancy. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O4 | 0.92054 (7) | 0.53494 (4) | 0.34391 (6) | 0.02196 (18) | |
H4 | 0.9694 (13) | 0.5029 (8) | 0.3919 (10) | 0.036 (4)* | |
O5 | 0.89935 (7) | 0.56424 (5) | 0.54461 (6) | 0.02841 (19) | |
O12 | 0.74321 (7) | 0.78349 (4) | 0.32650 (6) | 0.02110 (17) | |
O13 | 0.62305 (7) | 0.50977 (4) | 0.17572 (6) | 0.02460 (18) | |
O14 | 0.57795 (7) | 0.63387 (4) | 0.13538 (5) | 0.02211 (17) | |
O24 | 0.57281 (7) | 0.46110 (4) | 0.65771 (6) | 0.02178 (17) | |
H24 | 0.5220 (13) | 0.4929 (8) | 0.6090 (10) | 0.037 (4)* | |
O25 | 0.62108 (7) | 0.45310 (5) | 0.46170 (6) | 0.02536 (18) | |
O32 | 0.75626 (7) | 0.22738 (4) | 0.67378 (6) | 0.02102 (17) | |
O33 | 0.86974 (7) | 0.49392 (4) | 0.83546 (6) | 0.02598 (18) | |
O34 | 0.92397 (7) | 0.37003 (4) | 0.86969 (5) | 0.02279 (18) | |
N1 | 0.74582 (8) | 0.64686 (5) | 0.45417 (6) | 0.01942 (19) | |
N21A | 0.7786 (3) | 0.37341 (15) | 0.5535 (2) | 0.0190 (5) | 0.836 (4) |
N21B | 0.7542 (12) | 0.3575 (7) | 0.5456 (10) | 0.010 (2) | 0.164 (4) |
C2 | 0.66128 (9) | 0.65746 (6) | 0.35129 (7) | 0.0165 (2) | |
H2 | 0.578316 | 0.632617 | 0.344977 | 0.020* | |
C3 | 0.73003 (9) | 0.61026 (6) | 0.28976 (7) | 0.0170 (2) | |
H3 | 0.790211 | 0.644986 | 0.270707 | 0.020* | |
C4 | 0.80571 (9) | 0.55040 (6) | 0.36278 (7) | 0.0177 (2) | |
H4A | 0.755443 | 0.502061 | 0.356627 | 0.021* | |
C5 | 0.82458 (9) | 0.58678 (6) | 0.46509 (8) | 0.0199 (2) | |
C6 | 0.73069 (10) | 0.69195 (6) | 0.53755 (8) | 0.0236 (2) | |
H6A | 0.742435 | 0.747037 | 0.525414 | 0.028* | |
H6B | 0.796986 | 0.676924 | 0.599909 | 0.028* | |
C7 | 0.60199 (11) | 0.68079 (7) | 0.55144 (9) | 0.0272 (2) | |
H7A | 0.536009 | 0.696876 | 0.490555 | 0.041* | |
H7B | 0.596623 | 0.711818 | 0.608110 | 0.041* | |
H7C | 0.590373 | 0.626466 | 0.564593 | 0.041* | |
C8 | 0.63972 (9) | 0.73994 (6) | 0.32359 (7) | 0.0171 (2) | |
C9 | 0.53472 (10) | 0.78358 (6) | 0.29576 (8) | 0.0235 (2) | |
H9 | 0.451126 | 0.767162 | 0.288571 | 0.028* | |
C10 | 0.57344 (11) | 0.85940 (6) | 0.27913 (9) | 0.0275 (2) | |
H10 | 0.520635 | 0.903043 | 0.258338 | 0.033* | |
C11 | 0.69883 (11) | 0.85672 (6) | 0.29865 (8) | 0.0241 (2) | |
H11 | 0.750015 | 0.899272 | 0.293969 | 0.029* | |
C13 | 0.63899 (9) | 0.57705 (6) | 0.19511 (7) | 0.0180 (2) | |
C15 | 0.48291 (10) | 0.61143 (6) | 0.04229 (8) | 0.0240 (2) | |
H15A | 0.515009 | 0.567984 | 0.011778 | 0.029* | |
H15B | 0.466014 | 0.654974 | −0.005324 | 0.029* | |
C16 | 0.36226 (11) | 0.58807 (7) | 0.06123 (9) | 0.0299 (3) | |
H16A | 0.298029 | 0.576211 | −0.002580 | 0.045* | |
H16B | 0.332593 | 0.630269 | 0.094239 | 0.045* | |
H16C | 0.377678 | 0.542549 | 0.104343 | 0.045* | |
C22 | 0.84715 (9) | 0.35231 (6) | 0.65609 (7) | 0.0187 (2) | |
H22 | 0.933196 | 0.375704 | 0.673823 | 0.022* | 0.836 (4) |
H22A | 0.929708 | 0.377914 | 0.663058 | 0.022* | 0.164 (4) |
C23 | 0.77142 (9) | 0.39493 (6) | 0.71602 (7) | 0.0175 (2) | |
H23 | 0.712657 | 0.357492 | 0.732273 | 0.021* | |
C24 | 0.69331 (9) | 0.45539 (6) | 0.64507 (8) | 0.0183 (2) | |
H24A | 0.737082 | 0.506209 | 0.658916 | 0.022* | |
C25 | 0.68947 (10) | 0.42710 (6) | 0.54179 (8) | 0.0206 (2) | |
C26A | 0.81388 (15) | 0.34238 (9) | 0.46906 (10) | 0.0226 (4) | 0.836 (4) |
H26A | 0.905578 | 0.331540 | 0.491361 | 0.027* | 0.836 (4) |
H26B | 0.797032 | 0.381674 | 0.415622 | 0.027* | 0.836 (4) |
C27A | 0.74323 (14) | 0.26966 (10) | 0.42640 (11) | 0.0280 (4) | 0.836 (4) |
H27A | 0.769527 | 0.252054 | 0.369743 | 0.042* | 0.836 (4) |
H27B | 0.652344 | 0.280025 | 0.403650 | 0.042* | 0.836 (4) |
H27C | 0.762064 | 0.229808 | 0.478174 | 0.042* | 0.836 (4) |
C26B | 0.7672 (7) | 0.3099 (5) | 0.4613 (5) | 0.0171 (16) | 0.164 (4) |
H26C | 0.700974 | 0.324577 | 0.398667 | 0.020* | 0.164 (4) |
H26D | 0.755223 | 0.255071 | 0.474579 | 0.020* | 0.164 (4) |
C27B | 0.8968 (6) | 0.3210 (4) | 0.4482 (5) | 0.0252 (19) | 0.164 (4) |
H27D | 0.901656 | 0.291392 | 0.390257 | 0.038* | 0.164 (4) |
H27E | 0.962137 | 0.303087 | 0.508468 | 0.038* | 0.164 (4) |
H27F | 0.909998 | 0.375552 | 0.437640 | 0.038* | 0.164 (4) |
C28 | 0.86200 (9) | 0.26813 (6) | 0.67484 (7) | 0.0180 (2) | |
C29 | 0.96131 (10) | 0.22029 (6) | 0.68922 (8) | 0.0221 (2) | |
H29 | 1.044985 | 0.234227 | 0.692887 | 0.027* | |
C30 | 0.91611 (11) | 0.14452 (6) | 0.69787 (8) | 0.0265 (2) | |
H30 | 0.963761 | 0.098313 | 0.708368 | 0.032* | |
C31 | 0.79324 (11) | 0.15164 (6) | 0.68823 (8) | 0.0251 (2) | |
H31 | 0.739075 | 0.110162 | 0.690986 | 0.030* | |
C33 | 0.85854 (9) | 0.42696 (6) | 0.81275 (8) | 0.0191 (2) | |
C35 | 1.02196 (10) | 0.39294 (6) | 0.96107 (8) | 0.0231 (2) | |
H35A | 1.047642 | 0.348019 | 1.005995 | 0.028* | |
H35B | 0.988199 | 0.432567 | 0.996345 | 0.028* | |
C36 | 1.13534 (11) | 0.42451 (7) | 0.93702 (9) | 0.0298 (3) | |
H36A | 1.111568 | 0.471708 | 0.897679 | 0.045* | |
H36B | 1.165443 | 0.386445 | 0.898403 | 0.045* | |
H36C | 1.202567 | 0.435838 | 0.999384 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0195 (4) | 0.0234 (4) | 0.0257 (4) | 0.0059 (3) | 0.0110 (3) | 0.0062 (3) |
O5 | 0.0287 (4) | 0.0316 (4) | 0.0220 (4) | 0.0112 (3) | 0.0038 (3) | 0.0033 (3) |
O12 | 0.0218 (4) | 0.0168 (4) | 0.0264 (4) | −0.0026 (3) | 0.0099 (3) | 0.0002 (3) |
O13 | 0.0269 (4) | 0.0170 (4) | 0.0282 (4) | 0.0017 (3) | 0.0063 (3) | −0.0030 (3) |
O14 | 0.0263 (4) | 0.0180 (4) | 0.0188 (4) | −0.0001 (3) | 0.0024 (3) | 0.0013 (3) |
O24 | 0.0194 (4) | 0.0245 (4) | 0.0237 (4) | 0.0049 (3) | 0.0098 (3) | 0.0054 (3) |
O25 | 0.0261 (4) | 0.0287 (4) | 0.0228 (4) | 0.0069 (3) | 0.0098 (3) | 0.0084 (3) |
O32 | 0.0213 (4) | 0.0184 (4) | 0.0241 (4) | −0.0016 (3) | 0.0081 (3) | −0.0003 (3) |
O33 | 0.0294 (4) | 0.0167 (4) | 0.0289 (4) | 0.0024 (3) | 0.0048 (3) | −0.0032 (3) |
O34 | 0.0269 (4) | 0.0171 (4) | 0.0207 (4) | 0.0014 (3) | 0.0021 (3) | −0.0001 (3) |
N1 | 0.0212 (4) | 0.0200 (4) | 0.0169 (4) | 0.0024 (3) | 0.0057 (3) | 0.0005 (3) |
N21A | 0.0234 (12) | 0.0158 (11) | 0.0194 (9) | −0.0009 (7) | 0.0093 (8) | 0.0001 (7) |
N21B | 0.012 (4) | 0.008 (4) | 0.005 (3) | 0.000 (3) | −0.002 (3) | −0.003 (3) |
C2 | 0.0171 (5) | 0.0156 (5) | 0.0173 (5) | 0.0006 (3) | 0.0060 (4) | 0.0012 (4) |
C3 | 0.0175 (5) | 0.0149 (5) | 0.0201 (5) | 0.0004 (4) | 0.0080 (4) | 0.0012 (4) |
C4 | 0.0175 (5) | 0.0160 (5) | 0.0207 (5) | 0.0012 (4) | 0.0075 (4) | 0.0019 (4) |
C5 | 0.0189 (5) | 0.0202 (5) | 0.0213 (5) | 0.0011 (4) | 0.0071 (4) | 0.0029 (4) |
C6 | 0.0286 (6) | 0.0215 (5) | 0.0202 (5) | 0.0026 (4) | 0.0070 (4) | −0.0017 (4) |
C7 | 0.0345 (6) | 0.0262 (6) | 0.0252 (5) | 0.0023 (4) | 0.0154 (5) | −0.0002 (4) |
C8 | 0.0192 (5) | 0.0167 (5) | 0.0166 (4) | −0.0019 (4) | 0.0074 (4) | −0.0001 (4) |
C9 | 0.0222 (5) | 0.0200 (5) | 0.0283 (5) | 0.0027 (4) | 0.0081 (4) | 0.0024 (4) |
C10 | 0.0351 (6) | 0.0181 (5) | 0.0294 (6) | 0.0056 (4) | 0.0100 (5) | 0.0041 (4) |
C11 | 0.0364 (6) | 0.0148 (5) | 0.0226 (5) | −0.0034 (4) | 0.0113 (4) | 0.0006 (4) |
C13 | 0.0184 (5) | 0.0179 (5) | 0.0198 (5) | 0.0013 (4) | 0.0090 (4) | 0.0012 (4) |
C15 | 0.0276 (6) | 0.0257 (5) | 0.0167 (5) | −0.0021 (4) | 0.0039 (4) | 0.0001 (4) |
C16 | 0.0255 (6) | 0.0341 (6) | 0.0271 (6) | −0.0007 (5) | 0.0040 (5) | 0.0045 (5) |
C22 | 0.0192 (5) | 0.0186 (5) | 0.0200 (5) | 0.0021 (4) | 0.0085 (4) | 0.0015 (4) |
C23 | 0.0185 (5) | 0.0148 (5) | 0.0205 (5) | −0.0001 (4) | 0.0081 (4) | 0.0004 (4) |
C24 | 0.0177 (5) | 0.0160 (5) | 0.0222 (5) | 0.0008 (4) | 0.0078 (4) | 0.0025 (4) |
C25 | 0.0218 (5) | 0.0197 (5) | 0.0230 (5) | 0.0008 (4) | 0.0109 (4) | 0.0047 (4) |
C26A | 0.0303 (8) | 0.0201 (7) | 0.0219 (7) | 0.0029 (6) | 0.0144 (6) | 0.0013 (6) |
C27A | 0.0349 (8) | 0.0277 (9) | 0.0230 (7) | −0.0010 (6) | 0.0110 (6) | −0.0053 (6) |
C26B | 0.023 (3) | 0.010 (3) | 0.017 (3) | −0.007 (3) | 0.005 (2) | −0.006 (3) |
C27B | 0.026 (4) | 0.029 (4) | 0.022 (3) | −0.001 (3) | 0.010 (3) | 0.003 (3) |
C28 | 0.0199 (5) | 0.0187 (5) | 0.0160 (4) | −0.0008 (4) | 0.0066 (4) | −0.0006 (4) |
C29 | 0.0217 (5) | 0.0227 (5) | 0.0219 (5) | 0.0036 (4) | 0.0065 (4) | −0.0018 (4) |
C30 | 0.0351 (6) | 0.0182 (5) | 0.0257 (5) | 0.0060 (4) | 0.0087 (5) | −0.0019 (4) |
C31 | 0.0356 (6) | 0.0155 (5) | 0.0240 (5) | −0.0030 (4) | 0.0090 (5) | −0.0023 (4) |
C33 | 0.0195 (5) | 0.0172 (5) | 0.0219 (5) | 0.0014 (4) | 0.0085 (4) | 0.0010 (4) |
C35 | 0.0258 (5) | 0.0225 (5) | 0.0185 (5) | 0.0004 (4) | 0.0035 (4) | −0.0010 (4) |
C36 | 0.0257 (6) | 0.0356 (6) | 0.0263 (6) | 0.0001 (5) | 0.0055 (5) | 0.0009 (5) |
O4—H4 | 0.913 (12) | C10—H10 | 0.9500 |
O4—C4 | 1.4125 (12) | C10—C11 | 1.3394 (17) |
O5—C5 | 1.2324 (13) | C11—H11 | 0.9500 |
O12—C8 | 1.3709 (12) | C15—H15A | 0.9900 |
O12—C11 | 1.3796 (13) | C15—H15B | 0.9900 |
O13—C13 | 1.2033 (13) | C15—C16 | 1.5068 (15) |
O14—C13 | 1.3384 (12) | C16—H16A | 0.9800 |
O14—C15 | 1.4578 (12) | C16—H16B | 0.9800 |
O24—H24 | 0.925 (12) | C16—H16C | 0.9800 |
O24—C24 | 1.4130 (12) | C22—H22 | 1.0000 |
O25—C25 | 1.2328 (13) | C22—H22A | 1.0000 |
O32—C28 | 1.3725 (12) | C22—C23 | 1.5549 (13) |
O32—C31 | 1.3777 (13) | C22—C28 | 1.4892 (14) |
O33—C33 | 1.2048 (13) | C23—H23 | 1.0000 |
O34—C33 | 1.3387 (12) | C23—C24 | 1.5234 (13) |
O34—C35 | 1.4594 (12) | C23—C33 | 1.5107 (14) |
N1—C2 | 1.4718 (12) | C24—H24A | 1.0000 |
N1—C5 | 1.3437 (13) | C24—C25 | 1.5215 (14) |
N1—C6 | 1.4639 (13) | C26A—H26A | 0.9900 |
N21A—C22 | 1.453 (3) | C26A—H26B | 0.9900 |
N21A—C25 | 1.337 (3) | C26A—C27A | 1.513 (2) |
N21A—C26A | 1.466 (3) | C27A—H27A | 0.9800 |
N21B—C22 | 1.579 (13) | C27A—H27B | 0.9800 |
N21B—C25 | 1.403 (13) | C27A—H27C | 0.9800 |
N21B—C26B | 1.491 (14) | C26B—H26C | 0.9900 |
C2—H2 | 1.0000 | C26B—H26D | 0.9900 |
C2—C3 | 1.5574 (13) | C26B—C27B | 1.525 (9) |
C2—C8 | 1.4877 (13) | C27B—H27D | 0.9800 |
C3—H3 | 1.0000 | C27B—H27E | 0.9800 |
C3—C4 | 1.5208 (13) | C27B—H27F | 0.9800 |
C3—C13 | 1.5148 (14) | C28—C29 | 1.3497 (14) |
C4—H4A | 1.0000 | C29—H29 | 0.9500 |
C4—C5 | 1.5252 (14) | C29—C30 | 1.4310 (15) |
C6—H6A | 0.9900 | C30—H30 | 0.9500 |
C6—H6B | 0.9900 | C30—C31 | 1.3402 (17) |
C6—C7 | 1.5202 (15) | C31—H31 | 0.9500 |
C7—H7A | 0.9800 | C35—H35A | 0.9900 |
C7—H7B | 0.9800 | C35—H35B | 0.9900 |
C7—H7C | 0.9800 | C35—C36 | 1.5107 (15) |
C8—C9 | 1.3477 (14) | C36—H36A | 0.9800 |
C9—H9 | 0.9500 | C36—H36B | 0.9800 |
C9—C10 | 1.4306 (15) | C36—H36C | 0.9800 |
C4—O4—H4 | 110.1 (9) | N21A—C22—C28 | 114.80 (13) |
C8—O12—C11 | 106.17 (8) | N21B—C22—H22A | 111.9 |
C13—O14—C15 | 116.79 (8) | C23—C22—N21B | 101.8 (5) |
C24—O24—H24 | 109.6 (9) | C23—C22—H22 | 108.2 |
C28—O32—C31 | 106.05 (8) | C23—C22—H22A | 111.9 |
C33—O34—C35 | 116.32 (8) | C28—C22—N21B | 103.5 (4) |
C5—N1—C2 | 113.94 (8) | C28—C22—H22 | 108.2 |
C5—N1—C6 | 124.09 (9) | C28—C22—H22A | 111.9 |
C6—N1—C2 | 121.44 (8) | C28—C22—C23 | 115.02 (8) |
C22—N21A—C26A | 121.3 (2) | C22—C23—H23 | 108.6 |
C25—N21A—C22 | 116.1 (2) | C24—C23—C22 | 105.74 (8) |
C25—N21A—C26A | 122.3 (2) | C24—C23—H23 | 108.6 |
C25—N21B—C22 | 105.0 (7) | C33—C23—C22 | 111.02 (8) |
C25—N21B—C26B | 128.8 (11) | C33—C23—H23 | 108.6 |
C26B—N21B—C22 | 123.6 (10) | C33—C23—C24 | 114.25 (8) |
N1—C2—H2 | 108.9 | O24—C24—C23 | 109.79 (8) |
N1—C2—C3 | 101.80 (7) | O24—C24—H24A | 109.8 |
N1—C2—C8 | 112.34 (8) | O24—C24—C25 | 113.44 (8) |
C3—C2—H2 | 108.9 | C23—C24—H24A | 109.8 |
C8—C2—H2 | 108.9 | C25—C24—C23 | 103.99 (8) |
C8—C2—C3 | 115.55 (8) | C25—C24—H24A | 109.8 |
C2—C3—H3 | 108.5 | O25—C25—N21A | 126.46 (16) |
C4—C3—C2 | 104.61 (8) | O25—C25—N21B | 121.1 (6) |
C4—C3—H3 | 108.5 | O25—C25—C24 | 125.35 (9) |
C13—C3—C2 | 112.23 (8) | N21A—C25—C24 | 108.04 (16) |
C13—C3—H3 | 108.5 | N21B—C25—C24 | 112.5 (6) |
C13—C3—C4 | 114.26 (8) | N21A—C26A—H26A | 109.0 |
O4—C4—C3 | 110.41 (8) | N21A—C26A—H26B | 109.0 |
O4—C4—H4A | 109.9 | N21A—C26A—C27A | 113.06 (14) |
O4—C4—C5 | 112.93 (8) | H26A—C26A—H26B | 107.8 |
C3—C4—H4A | 109.9 | C27A—C26A—H26A | 109.0 |
C3—C4—C5 | 103.70 (8) | C27A—C26A—H26B | 109.0 |
C5—C4—H4A | 109.9 | C26A—C27A—H27A | 109.5 |
O5—C5—N1 | 125.80 (10) | C26A—C27A—H27B | 109.5 |
O5—C5—C4 | 125.39 (9) | C26A—C27A—H27C | 109.5 |
N1—C5—C4 | 108.80 (8) | H27A—C27A—H27B | 109.5 |
N1—C6—H6A | 109.1 | H27A—C27A—H27C | 109.5 |
N1—C6—H6B | 109.1 | H27B—C27A—H27C | 109.5 |
N1—C6—C7 | 112.55 (9) | N21B—C26B—H26C | 109.5 |
H6A—C6—H6B | 107.8 | N21B—C26B—H26D | 109.5 |
C7—C6—H6A | 109.1 | N21B—C26B—C27B | 110.9 (8) |
C7—C6—H6B | 109.1 | H26C—C26B—H26D | 108.1 |
C6—C7—H7A | 109.5 | C27B—C26B—H26C | 109.5 |
C6—C7—H7B | 109.5 | C27B—C26B—H26D | 109.5 |
C6—C7—H7C | 109.5 | C26B—C27B—H27D | 109.5 |
H7A—C7—H7B | 109.5 | C26B—C27B—H27E | 109.5 |
H7A—C7—H7C | 109.5 | C26B—C27B—H27F | 109.5 |
H7B—C7—H7C | 109.5 | H27D—C27B—H27E | 109.5 |
O12—C8—C2 | 117.40 (8) | H27D—C27B—H27F | 109.5 |
C9—C8—O12 | 110.13 (9) | H27E—C27B—H27F | 109.5 |
C9—C8—C2 | 132.46 (9) | O32—C28—C22 | 117.33 (8) |
C8—C9—H9 | 126.6 | C29—C28—O32 | 110.18 (9) |
C8—C9—C10 | 106.76 (10) | C29—C28—C22 | 132.42 (9) |
C10—C9—H9 | 126.6 | C28—C29—H29 | 126.7 |
C9—C10—H10 | 126.8 | C28—C29—C30 | 106.69 (10) |
C11—C10—C9 | 106.47 (10) | C30—C29—H29 | 126.7 |
C11—C10—H10 | 126.8 | C29—C30—H30 | 126.8 |
O12—C11—H11 | 124.8 | C31—C30—C29 | 106.40 (9) |
C10—C11—O12 | 110.47 (9) | C31—C30—H30 | 126.8 |
C10—C11—H11 | 124.8 | O32—C31—H31 | 124.7 |
O13—C13—O14 | 124.54 (9) | C30—C31—O32 | 110.68 (9) |
O13—C13—C3 | 125.59 (9) | C30—C31—H31 | 124.7 |
O14—C13—C3 | 109.87 (8) | O33—C33—O34 | 124.45 (10) |
O14—C15—H15A | 109.5 | O33—C33—C23 | 125.48 (9) |
O14—C15—H15B | 109.5 | O34—C33—C23 | 110.06 (8) |
O14—C15—C16 | 110.68 (9) | O34—C35—H35A | 109.5 |
H15A—C15—H15B | 108.1 | O34—C35—H35B | 109.5 |
C16—C15—H15A | 109.5 | O34—C35—C36 | 110.60 (9) |
C16—C15—H15B | 109.5 | H35A—C35—H35B | 108.1 |
C15—C16—H16A | 109.5 | C36—C35—H35A | 109.5 |
C15—C16—H16B | 109.5 | C36—C35—H35B | 109.5 |
C15—C16—H16C | 109.5 | C35—C36—H36A | 109.5 |
H16A—C16—H16B | 109.5 | C35—C36—H36B | 109.5 |
H16A—C16—H16C | 109.5 | C35—C36—H36C | 109.5 |
H16B—C16—H16C | 109.5 | H36A—C36—H36B | 109.5 |
N21A—C22—H22 | 108.2 | H36A—C36—H36C | 109.5 |
N21A—C22—C23 | 102.16 (14) | H36B—C36—H36C | 109.5 |
O4—C4—C5—O5 | −46.93 (14) | C13—C3—C4—O4 | 91.18 (10) |
O4—C4—C5—N1 | 133.51 (9) | C13—C3—C4—C5 | −147.57 (8) |
O12—C8—C9—C10 | 0.49 (12) | C15—O14—C13—O13 | 2.18 (14) |
O24—C24—C25—O25 | 49.78 (14) | C15—O14—C13—C3 | −177.78 (8) |
O24—C24—C25—N21A | −134.40 (14) | C22—N21A—C25—O25 | 179.90 (12) |
O24—C24—C25—N21B | −118.3 (5) | C22—N21A—C25—C24 | 4.1 (2) |
O32—C28—C29—C30 | −0.01 (12) | C22—N21A—C26A—C27A | 91.9 (2) |
N1—C2—C3—C4 | 25.90 (9) | C22—N21B—C25—O25 | 170.5 (4) |
N1—C2—C3—C13 | 150.32 (8) | C22—N21B—C25—C24 | −20.8 (8) |
N1—C2—C8—O12 | 60.01 (11) | C22—N21B—C26B—C27B | −56.6 (12) |
N1—C2—C8—C9 | −119.12 (12) | C22—C23—C24—O24 | 141.47 (8) |
N21A—C22—C23—C24 | −17.32 (13) | C22—C23—C24—C25 | 19.78 (10) |
N21A—C22—C23—C33 | −141.75 (12) | C22—C23—C33—O33 | 118.97 (11) |
N21A—C22—C28—O32 | −71.41 (16) | C22—C23—C33—O34 | −59.94 (10) |
N21A—C22—C28—C29 | 105.14 (18) | C22—C28—C29—C30 | −176.75 (11) |
N21B—C22—C23—C24 | −31.2 (4) | C23—C22—C28—O32 | 46.74 (12) |
N21B—C22—C23—C33 | −155.6 (4) | C23—C22—C28—C29 | −136.71 (11) |
N21B—C22—C28—O32 | −63.4 (5) | C23—C24—C25—O25 | 169.01 (10) |
N21B—C22—C28—C29 | 113.1 (5) | C23—C24—C25—N21A | −15.17 (15) |
C2—N1—C5—O5 | −176.23 (10) | C23—C24—C25—N21B | 0.9 (5) |
C2—N1—C5—C4 | 3.34 (11) | C24—C23—C33—O33 | −0.48 (14) |
C2—N1—C6—C7 | 59.57 (12) | C24—C23—C33—O34 | −179.40 (8) |
C2—C3—C4—O4 | −145.71 (8) | C25—N21A—C22—C23 | 8.5 (2) |
C2—C3—C4—C5 | −24.46 (10) | C25—N21A—C22—C28 | 133.66 (16) |
C2—C3—C13—O13 | −118.21 (11) | C25—N21A—C26A—C27A | −93.8 (2) |
C2—C3—C13—O14 | 61.74 (10) | C25—N21B—C22—C23 | 31.7 (8) |
C2—C8—C9—C10 | 179.67 (10) | C25—N21B—C22—C28 | 151.3 (6) |
C3—C2—C8—O12 | −56.19 (12) | C25—N21B—C26B—C27B | 102.6 (11) |
C3—C2—C8—C9 | 124.68 (12) | C26A—N21A—C22—C23 | −176.88 (17) |
C3—C4—C5—O5 | −166.46 (10) | C26A—N21A—C22—C28 | −51.7 (2) |
C3—C4—C5—N1 | 13.97 (10) | C26A—N21A—C25—O25 | 5.3 (3) |
C4—C3—C13—O13 | 0.67 (14) | C26A—N21A—C25—C24 | −170.44 (17) |
C4—C3—C13—O14 | −179.38 (8) | C26B—N21B—C22—C23 | −165.0 (9) |
C5—N1—C2—C3 | −18.63 (10) | C26B—N21B—C22—C28 | −45.4 (11) |
C5—N1—C2—C8 | −142.84 (9) | C26B—N21B—C25—O25 | 8.4 (14) |
C5—N1—C6—C7 | −111.54 (11) | C26B—N21B—C25—C24 | 177.1 (9) |
C6—N1—C2—C3 | 169.42 (9) | C28—O32—C31—C30 | −0.07 (12) |
C6—N1—C2—C8 | 45.21 (12) | C28—C22—C23—C24 | −142.36 (9) |
C6—N1—C5—O5 | −4.52 (17) | C28—C22—C23—C33 | 93.21 (10) |
C6—N1—C5—C4 | 175.04 (9) | C28—C29—C30—C31 | −0.03 (12) |
C8—O12—C11—C10 | 0.04 (12) | C29—C30—C31—O32 | 0.06 (12) |
C8—C2—C3—C4 | 147.93 (8) | C31—O32—C28—C22 | 177.33 (9) |
C8—C2—C3—C13 | −87.66 (10) | C31—O32—C28—C29 | 0.05 (11) |
C8—C9—C10—C11 | −0.45 (13) | C33—O34—C35—C36 | −74.74 (11) |
C9—C10—C11—O12 | 0.25 (13) | C33—C23—C24—O24 | −96.14 (10) |
C11—O12—C8—C2 | −179.65 (8) | C33—C23—C24—C25 | 142.16 (8) |
C11—O12—C8—C9 | −0.34 (11) | C35—O34—C33—O33 | −5.23 (15) |
C13—O14—C15—C16 | 78.82 (11) | C35—O34—C33—C23 | 173.70 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O5i | 0.91 (1) | 1.87 (1) | 2.7408 (10) | 159 (1) |
O24—H24···O25ii | 0.93 (1) | 1.85 (1) | 2.7323 (10) | 158 (1) |
C9—H9···O32ii | 0.95 | 2.53 | 3.4086 (13) | 154 |
C11—H11···O13iii | 0.95 | 2.35 | 3.2758 (13) | 165 |
C29—H29···O12i | 0.95 | 2.48 | 3.3717 (13) | 156 |
C31—H31···O33iv | 0.95 | 2.33 | 3.2525 (13) | 164 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+1/2; (iv) −x+3/2, y−1/2, −z+3/2. |
Acknowledgements
The authors acknowledge Universiti Teknologi MARA for financial support and the Centre of Chemical Synthesis & Polymer Technology (CCSPT), Institute of Science, Universiti Teknologi MARA Puncak Alam, Selangor, Malaysia for the provision of laboratory facilities.
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