research communications
E)-3-(anthracen-9-yl)-1-(4-nitrophenyl)prop-2-en-1-one
and optical properties of fused-ring chalcone (aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bSchool of Fundamental Science, Universiti Malaysia Terengganu, 21030, Kuala Terengganu, Terengganu, Malaysia
*Correspondence e-mail: suhanaarshad@usm.my
The title compound, C23H15NO3, adopts an s-cis conformation with respect to the ethylene C=C and carbonyl C=O double bonds in the enone unit. The molecule is significantly twisted with a dihedral angle of 48.63 (14)° between the anthracene ring system and the benzene ring. In the crystal, molecules are linked into inversion dimers with an R22(10) graph-set motif via pairs of C—H⋯O hydrogen bonds. The intermolecular interactions were analysed and quantified by Hirshfeld surface analysis. The molecular structure was optimized and a small HOMO–LUMO energy gap of 2.55 eV was obtained using the DFT method at the B3LYP/6–311 G++(d,p) level of theory. This value is in close agreement with the experimental value of 2.52 eV obtained from the UV–vis analysis. The crystal used was a two-component twin with a refined ratio of 0.1996 (16):0.8004 (16).
Keywords: chalcone; crystal structure; DFT; Hirshfeld surface; UV–Vis; HOMO–LUMO.
CCDC reference: 1905274
1. Chemical context
Conjugated organic molecules with multiple fused aromatic rings have attracted a great deal of interest from researchers because of their excellent performance in organic semiconductor devices (Gu et al., 2015). These organic molecules with a delocalized π-system represent attractive targets for applications in light-emitting diodes. In addition, the selection of the organic π-system with an (D) and an (A) is important because it exhibits an essential role in charge transfer in the molecule, where the aromatic groups may lead to delocalization of electronic charge distribution, imparting higher polarization of the push–pull configuration and generation of a molecular dipole (Bureš, 2014). An organic chalcone derivative with a π-conjugated system provides a large transfer axis with appropriate substituent groups on both terminal aromatic rings. The chalcone π-bridge consists of a α,β-unsaturated carbonyl unit which is responsible for intramolecular charge transfer. From the previous studies by Xu et al. (2015), the introduction of fused aromatic rings into the push–pull system could lead to enhanced carrier mobility and a lower band gap. In a continuation of our previous work on the effect of a fused-ring substituent, i.e. naphthalene or pyrene, on anthracene (Zaini et al., 2018), we have synthesized the title compound and report herein on its molecular and and optical properties.
2. Structural commentary
The title chalcone compound consists of an anthracene ring system and a para-substituted nitrobenzene unit, representing a donor–π–acceptor (D–π–A) system (Fig. 1a). The molecular structure was optimized with the Gaussian09W software package (Frisch et al., 2009) using the DFT method at the B3LYP/6-311G++(d,p) level of theory. All geometrical parameters calculated agree well with the experimental values. The compound adopts an s-cis conformation with respect to the C15=C16 [1.326 (5) Å; 1.347 (DFT) Å] and C17=O1 [1.232 (4) Å; 1.223 (DFT) Å] double bonds in the enone unit (C15=C16—C17=O1) and the structure is twisted around the C14—C15 bond with a C1—C14—C15—C16 torsion angle of 51.1 (6)° and slightly deviated around the C17—C18 bond with a C16—C17—C18—C19 torsion angle of −15.6 (5)°. The corresponding values by DFT are 44.8 and 18.5°, respectively (Fig. 1b). These large twist angles are due to the bulkiness of the strong-electron-donor anthracene ring system (Zainuri et al., 2018) and are also expected from the steric repulsion between the H atoms of the anthracene ring system and the ethylene group. In addition, the enone unit [maximum deviation 0.020 (3) Å at C17] forms dihedral angles of 52.0 (2) and 15.8 (2)°, respectively, with the anthracene ring system [C1–C14, maximum deviation of 0.034 (4) Å at C5] and the nitrobenzene ring [C18–C23, maximum deviation 0.011 (4) Å at C20] (Fig. 1c). Furthermore, a large dihedral angle of 48.63 (14)° is observed between the anthracene ring system and the nitrobenzene ring (Fig. 1d); this could diminish the electronic effect between the two ring systems (Jung et al., 2008).
3. Supramolecular features
In the crystal, the molecules are linked via pairs of intermolecular C—H⋯O interactions [C23—H23⋯O1i; symmetry code (i): −x + 1, −y + 2, −z + 1; Table 1), forming inversion dimers with an (10) graph-set motif. These dimers are stacked along the b-axis direction (Fig. 2).
The Hirshfeld surfaces and the related two dimensional fingerprint plots were generated using Crystal Explorer3.1 (Wolff et al., 2012). The dnorm and de surfaces are presented in Fig. 3a and Fig. 3b, respectively. In the dnorm surface, the bright-red spots indicate the intermolecular C—H⋯O interactions. These contacts are also confirmed by the pale-orange region marked with arrows in the de surface. The fingerprint plots (Ternavisk et al., 2014) of the intermolecular contacts with the corresponding dnorm surfaces (Fig. 4) show that the percentage contributions to the total Hirshfeld surface are 23.8, 19.6 and 12.6%, respectively, for the O⋯H/H⋯O, C⋯H/H⋯C and C⋯C contacts.
4. UV–vis analysis and frontier molecular orbitals
The measurement of the UV–vis −5 M) with cut-off wavelength of 190 nm. Two major peaks at 253 and 427 nm were observed (Fig. 5). The strong band of 253 nm was assigned to the n–π* transition. This sharp absorption peak arises due to the presence of carbonyl (C=O) and nitro substituent (NO2) functional groups (Zaini et al., 2018). The energy band gap of 2.52 eV was evaluated from the UV–vis (λa.e) at 492.06 nm (Fig. 5). This small band-gap energy is suitable for optoelectronic applications as previously reported for the structure of chalcone (Prabhu et al., 2016), and therefore exhibits a semiconducting nature (Rosencher & Vinter, 2002). The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO), known as obtained with the B3LYP/6-311G++(d,p) level calculation are illustrated in Fig. 6. The HOMO is mainly delocalized at the anthracene ring system. After excitation, the charge is localized at the enone and nitrobenzene moieties as depicted in the LUMO. The calculated HOMO–LUMO energy gap is 2.55 eV which is comparable with the UV–vis energy band gap obtained from the UV–vis absorption edge.
was carried out in an acetonitrile solution (105. Database survey
A search of the Cambridge Structural Database (Version 5.40, last update February 2019; Groom et al., 2016) revealed six closely related fused-ring namely, trans-3-(9-anthryl)-1-(4-methoxyphenyl)prop-2-en-1-one (refcode EMULIT; Zhang et al., 2016), 3-(anthracen-9-yl)-1-(4-chlorophenyl)prop-2-en-1-one (JAHPUG; Yu et al., 2017), (E)-3-(anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one (POPBAY; Suwunwong et al., 2009), (Z)-3-(anthracen-9-yl)-1-(2-ethoxyphenyl)prop-2-en-1-one (KABHUS; Joothamongkhon et al., 2010), (E)-3-(anthracen-9-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (UNUDUD; Jasinski et al., 2011; UNUDUD01; Chantrapromma et al., 2011), (E)-3-(anthracen-9-yl)-1-(2-bromophenyl)prop-2-en-1-one (WAFGOB; Fun et al., 2010). Compounds EMULIT, JAHPUG and POPBAY are methoxy, chloro and bromo derivatives, respectively, substituted at the para position on the phenyl ring, while compounds KABHUS, UNUDUD (UNUDUD01) and WAFGOB are ortho-substituted ethoxy, hydroxy and bromo derivatives, respectively. Dihedral angles between the enone unit and the anthracene ring system and between the enone unit and the benzene ring are 81.6 (3) and 8.2 (4)°, respectively, for EMULIJ, 47.1 (3) and 22.9 (3)° for JAHPUG, 45.79 (10) and 20.88 (11)° for POPBAY, 82.49 (11) and 35.54 (13)° for KABHUS, 61.51 (9) and 14.56 (10)° [62.05 (9) and 11.04 (10)°] for UNUDUD, and 42.62 (16) and 63.00 (17)° for WAFGOB. The large dihedral angle of 82.49 (11)° between the enone unit and the anthracene ring system observed for KABHUS is due to the Z configuration of the molecule. Interestingly, EMULIJ with an E configuration also shows a large dihedral angle of 81.6 (3)° between the enone unit and the anthracene ring system, whereas the dihedral angle between the enone unit and the benzene ring is extremely small [8.2 (4)°].
6. Synthesis and crystallization
A mixture of 4-nitroacetophenone (0.5 mmol) and 9-anthracencarboxaldehyde (0.5 mmol) was dissolved in methanol (20 ml) and the solution stirred continuously. A catalytic amount of NaOH (5 ml, 20%) was added to the solution dropwise until a precipitate formed and the reaction was stirred continuously for about 5 h at room temperature. After stirring, the solution was poured into 60 ml of ice-cold distilled water. The resultant crude product was filtered and washed several times with with distilled water until the filtrate turned colourless. The dried precipitate was further recrystallized to obtain the corresponding chalcone. Red plate-shaped single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.
7. Refinement
Crystal data, data collection and structure . The C-bound H atoms were placed in calculated positions (C—H = 0.93 Å) and were included in the in the riding-model approximation, with Uiso(H) = 1.2Ueq(C). Four outliers (002), (420), (300) and (52) were omitted in the last cycle of The crystal used was a two-component twin (twin law 0 0 0 0 1 0 1). The refined ratio of the twin components was 0.1996 (16):0.8004 (16).
details are summarized in Table 2Supporting information
CCDC reference: 1905274
https://doi.org/10.1107/S2056989019005243/is5513sup1.cif
contains datablocks I, mo_MFZ5_w_0m. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005243/is5513Isup2.hkl
Comparison of bond lengths and angles between experimental and theoretical studies. DOI: https://doi.org/10.1107/S2056989019005243/is5513sup3.docx
Supporting information file. DOI: https://doi.org/10.1107/S2056989019005243/is5513Isup4.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H15NO3 | F(000) = 736 |
Mr = 353.36 | Dx = 1.375 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8204 (10) Å | Cell parameters from 9886 reflections |
b = 3.9364 (3) Å | θ = 2.3–30.2° |
c = 40.420 (3) Å | µ = 0.09 mm−1 |
β = 97.651 (3)° | T = 296 K |
V = 1706.3 (2) Å3 | Plate, red |
Z = 4 | 0.26 × 0.17 × 0.08 mm |
Bruker APEXII CCD diffractometer | 2570 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.113 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 26.0°, θmin = 1.5° |
Tmin = 0.771, Tmax = 0.970 | h = −13→13 |
45734 measured reflections | k = −4→4 |
3608 independent reflections | l = −49→49 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.074 | H-atom parameters constrained |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.0651P)2 + 1.4385P], where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3608 reflections | Δρmax = 0.20 e Å−3 |
245 parameters | Δρmin = −0.21 e Å−3 |
Experimental. The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 0.71075 3.957 11.583 40.623 82.797 90.074 69.980 |
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 twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4171 (2) | 0.9048 (7) | 0.44992 (6) | 0.0512 (7) | |
O2 | 0.0772 (4) | 0.1119 (11) | 0.57047 (8) | 0.0950 (12) | |
O3 | 0.2506 (4) | 0.2855 (14) | 0.59652 (8) | 0.1070 (16) | |
N1 | 0.1793 (4) | 0.2508 (11) | 0.57135 (9) | 0.0638 (10) | |
C1 | 0.1551 (3) | 0.5116 (9) | 0.33952 (8) | 0.0394 (9) | |
C2 | 0.0565 (4) | 0.6557 (11) | 0.35514 (8) | 0.0487 (10) | |
H2A | 0.0749 | 0.7540 | 0.3761 | 0.058* | |
C3 | −0.0635 (4) | 0.6530 (12) | 0.34009 (9) | 0.0572 (11) | |
H3A | −0.1260 | 0.7449 | 0.3511 | 0.069* | |
C4 | −0.0939 (4) | 0.5133 (13) | 0.30826 (10) | 0.0601 (12) | |
H4A | −0.1765 | 0.5128 | 0.2983 | 0.072* | |
C5 | −0.0048 (4) | 0.3793 (11) | 0.29185 (9) | 0.0527 (10) | |
H5A | −0.0269 | 0.2860 | 0.2708 | 0.063* | |
C6 | 0.1232 (3) | 0.3783 (10) | 0.30643 (8) | 0.0420 (9) | |
C7 | 0.2156 (4) | 0.2487 (10) | 0.28935 (8) | 0.0469 (9) | |
H7A | 0.1936 | 0.1626 | 0.2679 | 0.056* | |
C8 | 0.3404 (4) | 0.2438 (10) | 0.30333 (8) | 0.0433 (9) | |
C9 | 0.4357 (4) | 0.1017 (11) | 0.28588 (9) | 0.0537 (10) | |
H9A | 0.4140 | 0.0136 | 0.2645 | 0.064* | |
C10 | 0.5562 (4) | 0.0937 (12) | 0.29994 (10) | 0.0598 (11) | |
H10A | 0.6172 | 0.0086 | 0.2880 | 0.072* | |
C11 | 0.5891 (4) | 0.2144 (12) | 0.33262 (10) | 0.0604 (11) | |
H11A | 0.6717 | 0.2002 | 0.3424 | 0.072* | |
C12 | 0.5027 (3) | 0.3513 (11) | 0.35013 (9) | 0.0513 (10) | |
H12A | 0.5275 | 0.4338 | 0.3715 | 0.062* | |
C13 | 0.3747 (3) | 0.3710 (9) | 0.33633 (8) | 0.0399 (8) | |
C14 | 0.2818 (3) | 0.5076 (9) | 0.35409 (8) | 0.0377 (8) | |
C15 | 0.3204 (3) | 0.6376 (9) | 0.38796 (8) | 0.0423 (9) | |
H15A | 0.3855 | 0.7937 | 0.3901 | 0.051* | |
C16 | 0.2745 (4) | 0.5611 (9) | 0.41586 (8) | 0.0424 (9) | |
H16A | 0.2055 | 0.4190 | 0.4149 | 0.051* | |
C17 | 0.3311 (3) | 0.6979 (9) | 0.44821 (8) | 0.0367 (8) | |
C18 | 0.2866 (3) | 0.5810 (8) | 0.47993 (7) | 0.0345 (8) | |
C19 | 0.1747 (3) | 0.4084 (10) | 0.48049 (8) | 0.0447 (9) | |
H19A | 0.1239 | 0.3599 | 0.4606 | 0.054* | |
C20 | 0.1392 (4) | 0.3096 (10) | 0.51059 (9) | 0.0481 (10) | |
H20A | 0.0636 | 0.1987 | 0.5111 | 0.058* | |
C21 | 0.2152 (3) | 0.3743 (10) | 0.53969 (8) | 0.0433 (9) | |
C22 | 0.3264 (3) | 0.5453 (10) | 0.53986 (8) | 0.0448 (9) | |
H22A | 0.3775 | 0.5890 | 0.5598 | 0.054* | |
C23 | 0.3599 (3) | 0.6495 (10) | 0.50987 (8) | 0.0412 (9) | |
H23A | 0.4338 | 0.7694 | 0.5097 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0545 (16) | 0.0532 (16) | 0.0449 (13) | −0.0130 (15) | 0.0028 (12) | −0.0031 (13) |
O2 | 0.087 (2) | 0.121 (3) | 0.083 (2) | −0.033 (3) | 0.0344 (19) | 0.006 (2) |
O3 | 0.095 (3) | 0.178 (5) | 0.0471 (17) | −0.025 (3) | 0.0076 (18) | 0.017 (2) |
N1 | 0.069 (2) | 0.073 (3) | 0.053 (2) | −0.001 (2) | 0.0200 (19) | 0.0001 (19) |
C1 | 0.051 (2) | 0.0347 (19) | 0.0338 (17) | 0.0008 (17) | 0.0093 (16) | 0.0037 (15) |
C2 | 0.058 (3) | 0.051 (2) | 0.0376 (18) | 0.007 (2) | 0.0070 (18) | 0.0028 (18) |
C3 | 0.052 (2) | 0.067 (3) | 0.053 (2) | 0.013 (2) | 0.0126 (19) | 0.012 (2) |
C4 | 0.050 (2) | 0.073 (3) | 0.055 (2) | 0.002 (2) | −0.003 (2) | 0.013 (2) |
C5 | 0.062 (3) | 0.053 (2) | 0.041 (2) | −0.007 (2) | −0.0009 (19) | 0.0046 (19) |
C6 | 0.051 (2) | 0.041 (2) | 0.0337 (17) | −0.0066 (19) | 0.0058 (16) | 0.0053 (16) |
C7 | 0.069 (3) | 0.039 (2) | 0.0327 (17) | −0.003 (2) | 0.0071 (18) | −0.0038 (16) |
C8 | 0.058 (2) | 0.0345 (19) | 0.0385 (18) | 0.0002 (19) | 0.0109 (18) | 0.0030 (16) |
C9 | 0.067 (3) | 0.049 (2) | 0.047 (2) | 0.002 (2) | 0.019 (2) | −0.0030 (19) |
C10 | 0.062 (3) | 0.055 (3) | 0.068 (3) | 0.009 (2) | 0.028 (2) | 0.004 (2) |
C11 | 0.050 (2) | 0.062 (3) | 0.070 (3) | 0.002 (2) | 0.012 (2) | 0.007 (2) |
C12 | 0.051 (2) | 0.054 (3) | 0.049 (2) | 0.001 (2) | 0.0065 (19) | 0.0017 (19) |
C13 | 0.050 (2) | 0.0312 (18) | 0.0397 (18) | 0.0006 (18) | 0.0097 (16) | 0.0052 (16) |
C14 | 0.047 (2) | 0.0307 (19) | 0.0352 (17) | −0.0004 (17) | 0.0048 (15) | 0.0031 (15) |
C15 | 0.048 (2) | 0.0350 (19) | 0.0425 (18) | −0.0003 (18) | 0.0015 (16) | −0.0009 (16) |
C16 | 0.052 (2) | 0.0357 (19) | 0.0382 (18) | 0.0012 (19) | 0.0019 (16) | 0.0003 (16) |
C17 | 0.035 (2) | 0.0345 (19) | 0.0395 (18) | 0.0067 (18) | 0.0008 (15) | −0.0026 (15) |
C18 | 0.0365 (19) | 0.0290 (17) | 0.0370 (17) | 0.0099 (16) | 0.0013 (14) | −0.0049 (15) |
C19 | 0.040 (2) | 0.050 (2) | 0.0421 (19) | 0.0021 (19) | −0.0001 (16) | −0.0099 (18) |
C20 | 0.044 (2) | 0.047 (2) | 0.055 (2) | −0.0051 (19) | 0.0129 (18) | −0.0060 (19) |
C21 | 0.047 (2) | 0.045 (2) | 0.0392 (18) | 0.011 (2) | 0.0118 (16) | −0.0021 (17) |
C22 | 0.042 (2) | 0.054 (2) | 0.0371 (18) | 0.007 (2) | 0.0015 (15) | −0.0059 (17) |
C23 | 0.039 (2) | 0.044 (2) | 0.0396 (18) | 0.0033 (18) | 0.0036 (15) | −0.0052 (17) |
O1—C17 | 1.232 (4) | C10—H10A | 0.9300 |
O2—N1 | 1.229 (5) | C11—C12 | 1.358 (5) |
O3—N1 | 1.200 (4) | C11—H11A | 0.9300 |
N1—C21 | 1.468 (5) | C12—C13 | 1.424 (5) |
C1—C14 | 1.418 (5) | C12—H12A | 0.9300 |
C1—C2 | 1.427 (5) | C13—C14 | 1.417 (5) |
C1—C6 | 1.435 (5) | C14—C15 | 1.469 (5) |
C2—C3 | 1.359 (5) | C15—C16 | 1.326 (5) |
C2—H2A | 0.9300 | C15—H15A | 0.9300 |
C3—C4 | 1.398 (6) | C16—C17 | 1.470 (5) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.348 (6) | C17—C18 | 1.500 (5) |
C4—H4A | 0.9300 | C18—C23 | 1.382 (4) |
C5—C6 | 1.431 (5) | C18—C19 | 1.392 (5) |
C5—H5A | 0.9300 | C19—C20 | 1.379 (5) |
C6—C7 | 1.386 (5) | C19—H19A | 0.9300 |
C7—C8 | 1.393 (5) | C20—C21 | 1.366 (5) |
C7—H7A | 0.9300 | C20—H20A | 0.9300 |
C8—C13 | 1.427 (5) | C21—C22 | 1.378 (5) |
C8—C9 | 1.438 (5) | C22—C23 | 1.373 (5) |
C9—C10 | 1.352 (6) | C22—H22A | 0.9300 |
C9—H9A | 0.9300 | C23—H23A | 0.9300 |
C10—C11 | 1.404 (6) | ||
O3—N1—O2 | 123.3 (4) | C11—C12—C13 | 121.2 (4) |
O3—N1—C21 | 119.1 (4) | C11—C12—H12A | 119.4 |
O2—N1—C21 | 117.6 (4) | C13—C12—H12A | 119.4 |
C14—C1—C2 | 123.9 (3) | C14—C13—C12 | 122.7 (3) |
C14—C1—C6 | 118.8 (3) | C14—C13—C8 | 119.5 (3) |
C2—C1—C6 | 117.2 (3) | C12—C13—C8 | 117.8 (3) |
C3—C2—C1 | 121.6 (3) | C13—C14—C1 | 120.4 (3) |
C3—C2—H2A | 119.2 | C13—C14—C15 | 118.1 (3) |
C1—C2—H2A | 119.2 | C1—C14—C15 | 121.5 (3) |
C2—C3—C4 | 120.6 (4) | C16—C15—C14 | 128.4 (4) |
C2—C3—H3A | 119.7 | C16—C15—H15A | 115.8 |
C4—C3—H3A | 119.7 | C14—C15—H15A | 115.8 |
C5—C4—C3 | 120.7 (4) | C15—C16—C17 | 121.0 (4) |
C5—C4—H4A | 119.6 | C15—C16—H16A | 119.5 |
C3—C4—H4A | 119.6 | C17—C16—H16A | 119.5 |
C4—C5—C6 | 121.0 (4) | O1—C17—C16 | 120.9 (3) |
C4—C5—H5A | 119.5 | O1—C17—C18 | 118.7 (3) |
C6—C5—H5A | 119.5 | C16—C17—C18 | 120.3 (3) |
C7—C6—C5 | 121.2 (3) | C23—C18—C19 | 118.7 (3) |
C7—C6—C1 | 119.9 (3) | C23—C18—C17 | 118.5 (3) |
C5—C6—C1 | 118.8 (3) | C19—C18—C17 | 122.8 (3) |
C6—C7—C8 | 121.8 (3) | C20—C19—C18 | 119.8 (3) |
C6—C7—H7A | 119.1 | C20—C19—H19A | 120.1 |
C8—C7—H7A | 119.1 | C18—C19—H19A | 120.1 |
C7—C8—C13 | 119.5 (3) | C21—C20—C19 | 120.1 (4) |
C7—C8—C9 | 121.8 (3) | C21—C20—H20A | 120.0 |
C13—C8—C9 | 118.7 (3) | C19—C20—H20A | 120.0 |
C10—C9—C8 | 121.2 (4) | C20—C21—C22 | 121.3 (3) |
C10—C9—H9A | 119.4 | C20—C21—N1 | 119.3 (4) |
C8—C9—H9A | 119.4 | C22—C21—N1 | 119.3 (3) |
C9—C10—C11 | 119.8 (4) | C23—C22—C21 | 118.3 (3) |
C9—C10—H10A | 120.1 | C23—C22—H22A | 120.9 |
C11—C10—H10A | 120.1 | C21—C22—H22A | 120.9 |
C12—C11—C10 | 121.2 (4) | C22—C23—C18 | 121.8 (4) |
C12—C11—H11A | 119.4 | C22—C23—H23A | 119.1 |
C10—C11—H11A | 119.4 | C18—C23—H23A | 119.1 |
C14—C1—C2—C3 | 180.0 (4) | C8—C13—C14—C15 | −179.7 (3) |
C6—C1—C2—C3 | 3.1 (6) | C2—C1—C14—C13 | −177.5 (3) |
C1—C2—C3—C4 | −1.3 (7) | C6—C1—C14—C13 | −0.6 (5) |
C2—C3—C4—C5 | −0.1 (7) | C2—C1—C14—C15 | 3.6 (6) |
C3—C4—C5—C6 | −0.4 (7) | C6—C1—C14—C15 | −179.5 (3) |
C4—C5—C6—C7 | −178.4 (4) | C13—C14—C15—C16 | −127.8 (4) |
C4—C5—C6—C1 | 2.3 (6) | C1—C14—C15—C16 | 51.1 (6) |
C14—C1—C6—C7 | 0.1 (5) | C14—C15—C16—C17 | 175.5 (3) |
C2—C1—C6—C7 | 177.1 (3) | C15—C16—C17—O1 | 5.0 (5) |
C14—C1—C6—C5 | 179.4 (3) | C15—C16—C17—C18 | −173.6 (3) |
C2—C1—C6—C5 | −3.5 (5) | O1—C17—C18—C23 | −13.9 (5) |
C5—C6—C7—C8 | −179.5 (4) | C16—C17—C18—C23 | 164.7 (3) |
C1—C6—C7—C8 | −0.2 (6) | O1—C17—C18—C19 | 165.7 (3) |
C6—C7—C8—C13 | 0.9 (6) | C16—C17—C18—C19 | −15.6 (5) |
C6—C7—C8—C9 | 178.5 (4) | C23—C18—C19—C20 | −0.1 (5) |
C7—C8—C9—C10 | −179.0 (4) | C17—C18—C19—C20 | −179.7 (3) |
C13—C8—C9—C10 | −1.4 (6) | C18—C19—C20—C21 | −1.4 (6) |
C8—C9—C10—C11 | 2.4 (7) | C19—C20—C21—C22 | 1.6 (6) |
C9—C10—C11—C12 | −2.4 (7) | C19—C20—C21—N1 | −176.7 (4) |
C10—C11—C12—C13 | 1.4 (7) | O3—N1—C21—C20 | 174.4 (4) |
C11—C12—C13—C14 | 179.0 (4) | O2—N1—C21—C20 | −4.7 (6) |
C11—C12—C13—C8 | −0.4 (6) | O3—N1—C21—C22 | −3.9 (6) |
C7—C8—C13—C14 | −1.5 (5) | O2—N1—C21—C22 | 177.1 (4) |
C9—C8—C13—C14 | −179.1 (3) | C20—C21—C22—C23 | −0.2 (6) |
C7—C8—C13—C12 | 178.0 (4) | N1—C21—C22—C23 | 178.1 (3) |
C9—C8—C13—C12 | 0.3 (5) | C21—C22—C23—C18 | −1.4 (5) |
C12—C13—C14—C1 | −178.1 (4) | C19—C18—C23—C22 | 1.5 (5) |
C8—C13—C14—C1 | 1.3 (5) | C17—C18—C23—C22 | −178.8 (3) |
C12—C13—C14—C15 | 0.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O1i | 0.93 | 2.49 | 3.240 (4) | 138 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Funding information
The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for providing facilities, Fundamental Research Grant Scheme (FRGS) No. 203.PFIZIK.6711606 and Research University Grant (RUI) No. 1001.PFIZIK.8011081 for supplying the chemicals to conduct this research.
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