research communications
of 2-(4-acetylanilino)-2-oxoethyl 3-(4-hydroxyphenyl)propionate
aDepartment of Biology, College of Natural Sciences, Kongju National University, Gongju 314-701, Republic of Korea, bDepartment of Chemistry, Allama Iqbal Open University, Islamabad 44000, Pakistan, and cDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
*Correspondence e-mail: skkang@cnu.ac.kr
In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms. The 4-hydroxyhydrocinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12). The N—(C=O)—C plane of the acetamide group and the acetate O—(C=O)—C plane are almost co-planar; the acetamide plane makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the acetate planes of the major and minor occupancy components. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds link the molecules into a supramolecular sheet structure parallel to (102).
CCDC reference: 1483293
1. Chemical context
Hydroxy-substituted aromatic compounds with additional ester and amide functionalities have been reported to be potential tyrosinase inhibitors (Miliovsky et al., 2013; Takahashi & Miyazawa, 2011). Tyrosinase is a key enzyme present in melanocytes, which is involved in the biosynthesis of melanin. The abnormal production and accumulation of melanin causes a number of hyperpigmentation disorders such as freckles, melasma, lentigo senilis and pigmented acne scars (Lynde et al., 2006; Cullen, 1998). Tyrosinase has also been linked to melanoma, a skin-cancer type that arises from the aberrant proliferation of melanocytes (Uong & Zon, 2010). It has also been reported that tyrosinase is one of the main causes of most fruit and vegetable damage during post-harvest handling and processing, leading to quicker degradation and shorter shelf life (Yi et al., 2010). Therefore, the synthesis of safe and effective tyrosinase inhibitors is of great concern in the medical, agricultural and cosmetic industries. The synthesis and tyrosinase inhibitory activity of hydroxy-substituted phenyl is currently an ongoing research topic in our lab (Ashraf et al., 2015). In view of the tyrosinase inhibitory potential of hydroxy-substituted aromatic compounds, the title compound (Fig. 1) has been synthesized and characterized by single crystal X-ray diffraction.
2. Structural commentary
The fragment O1/O12/N10/C2–C9/C11/C13 including the acetamide group is almost planar with an r.m.s. deviation of 0.034 (11) Å. The 4-hydroxyhydrocinnamate fragment is disordered over two positions with occupancy ratio of 0.729 (12):0.271 (12). The acetamide plane O12/N10/C11/C12 makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the disordered acetate planes O14/O16/C15/C17 and O14A/O16A/C15A/C17A. The carbonyl O1 and O16 atoms are positioned anti with respect to the carbonyl O12 atom. These C=O bond lengths are in the range 1.176 (12)–1.226 (6) Å.
3. Supramolecular features
In the crystal, molecules are linked via N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds (N10—H10⋯O1i, O25—H25⋯O12ii, C4—H4A⋯O16iii and C24—H24⋯O12ii; Table 1), forming a sheet parallel to (102) (Fig. 2). In the sheet, these hydrogen bonds form R21(6), R33(19) and R33(31) graph-set motifs. There are also weak C—H⋯O hydrogen bonds (C13—H13B⋯O25iv and C13—H13B⋯O25Aiv; Table 1) between the sheets (Fig. 3).
4. Database survey
A search of the Cambridge Structural Database (Version 5.37 with two updates, Groom et al., 2016) returned three entries for crystal structures with ethyl hydrocinnamate as the main skeleton (BESTIC: Böjthe-Horváth et al., 1982; FUZYOQ: Wang et al., 2015; NAXVIR: Hassan & Wang, 1997). There are 76 entries of organic compounds with the 4-acetylanilino group.
5. Synthesis and crystallization
The title compound was synthesized by direct condensation of 4-hydroxyphenyl propanoic acid with N-(4-acetylphenyl)-2-chloroacetamide in the presence of dimethyl formamide (DMF) solvent and triethylamine base (Fig. 4). The reaction mixture was stirred overnight at room temperature. Then the mixture was poured into finely crushed ice and extracted with ethyl acetate. It was washed with 5% HCl and 5% sodium hydroxide, and finally with aqueous NaCl solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure to afford the crude product. The title compound was purified by silica gel using ethyl acetate and n-hexane (3:1) as The single crystals were obtained from a solvent mixture of ethyl acetate/n-hexane (3:1) upon slow evaporation at room temperature (yield 78%, m.p. 419–421 K). FTIR νmax cm−1: 3428 (N—H), 3354 (O—H), 2971 (sp2 C—H), 2887 (sp3 C—H), 1735 (C=O ester), 1646 (C=O amide), 1601 (C=C aromatic), 1154 (C—O, ester).
6. Refinement
Crystal data, data collection and structure . The 4-hydroxyhydrocinnamate fragment, O16/O25/C15–C24, was found to be disordered over two positions and the occupancy ratio was refined to 0.729 (12):0.271 (12). Atoms O16A, O25A and C15A–C24A of the minor component were refined isotropically. Planarity restraints were applied for atoms C18–C24, O25, C18A–C24A and O25A. Bond-distance restraints were also applied for C20, C22, C23, O16A and C15A–C24A. H10 and H25 of the NH and OH groups, respectively, were located in a difference Fourier map and the coordinates were refined with Uiso(H) = 1.2Ueq(N) and 1.5Ueq(O) [N—H = 0.86 (5) Å and O—H = 0.95 (12) Å]. H25A of the minor occupancy OH group was refined with a restraint of O—H = 0.90 (2) Å, and with Uiso(H) = 1.5Ueq(O). All other H atoms were included as riding atoms, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) otherwise.
details are summarized in Table 2
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Supporting information
CCDC reference: 1483293
https://doi.org/10.1107/S205698901600894X/is5453sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901600894X/is5453Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S205698901600894X/is5453Isup3.cml
Data collection: SMART (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip,2010).C19H19NO5 | F(000) = 360 |
Mr = 341.35 | Dx = 1.306 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.510 (3) Å | Cell parameters from 1529 reflections |
b = 14.809 (9) Å | θ = 2.4–20.5° |
c = 10.824 (7) Å | µ = 0.10 mm−1 |
β = 100.757 (7)° | T = 296 K |
V = 867.7 (9) Å3 | Block, colourless |
Z = 2 | 0.26 × 0.25 × 0.23 mm |
Bruker SMART CCD area-detector diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 26.5°, θmin = 1.9° |
φ and ω scans | h = −6→6 |
6909 measured reflections | k = −18→18 |
3403 independent reflections | l = −13→13 |
1798 reflections with I > 2σ(I) |
Refinement on F2 | 25 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.0787P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3403 reflections | Δρmax = 0.14 e Å−3 |
276 parameters | Δρmin = −0.17 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 1.0367 (8) | 1.4286 (2) | 0.0585 (4) | 0.0831 (15) | |
C2 | 0.8795 (10) | 1.3999 (4) | 0.1151 (5) | 0.0551 (15) | |
C3 | 0.8377 (10) | 1.3024 (3) | 0.1253 (5) | 0.0451 (14) | |
C4 | 0.7281 (11) | 1.4662 (3) | 0.1753 (6) | 0.0689 (18) | |
H4A | 0.7711 | 1.5267 | 0.1559 | 0.103* | |
H4B | 0.7615 | 1.4578 | 0.2648 | 0.103* | |
H4C | 0.5557 | 1.4562 | 0.1434 | 0.103* | |
C5 | 0.9784 (9) | 1.2426 (4) | 0.0675 (5) | 0.0555 (16) | |
H5 | 1.0986 | 1.2651 | 0.0258 | 0.067* | |
C6 | 0.9408 (10) | 1.1512 (3) | 0.0717 (5) | 0.0523 (15) | |
H6 | 1.0375 | 1.1123 | 0.0339 | 0.063* | |
C7 | 0.7613 (9) | 1.1162 (3) | 0.1315 (5) | 0.0459 (14) | |
C8 | 0.6218 (11) | 1.1739 (3) | 0.1902 (5) | 0.0572 (17) | |
H8 | 0.5016 | 1.1509 | 0.2315 | 0.069* | |
C9 | 0.6618 (9) | 1.2656 (3) | 0.1872 (5) | 0.0540 (16) | |
H9 | 0.5684 | 1.3039 | 0.2278 | 0.065* | |
N10 | 0.7347 (8) | 1.0214 (3) | 0.1292 (4) | 0.0511 (13) | |
H10 | 0.836 (9) | 0.995 (4) | 0.089 (4) | 0.061* | |
C11 | 0.5765 (10) | 0.9683 (4) | 0.1782 (5) | 0.0500 (15) | |
O12 | 0.4168 (7) | 0.9955 (2) | 0.2321 (4) | 0.0621 (11) | |
C13 | 0.6264 (11) | 0.8699 (3) | 0.1599 (5) | 0.0509 (15) | |
H13A | 0.6134 | 0.8570 | 0.0710 | 0.061* | |
H13B | 0.7923 | 0.8548 | 0.2024 | 0.061* | |
O14 | 0.4514 (7) | 0.8175 (2) | 0.2098 (4) | 0.0650 (12) | |
C15 | 0.4672 (17) | 0.7263 (6) | 0.1902 (11) | 0.044 (3) | 0.729 (12) |
O16 | 0.631 (3) | 0.6938 (5) | 0.1497 (16) | 0.074 (4) | 0.729 (12) |
C17 | 0.2874 (14) | 0.6724 (5) | 0.2509 (9) | 0.048 (2) | 0.729 (12) |
H17A | 0.2446 | 0.6169 | 0.2042 | 0.058* | 0.729 (12) |
H17B | 0.1372 | 0.7070 | 0.2487 | 0.058* | 0.729 (12) |
C18 | 0.4021 (15) | 0.6501 (7) | 0.3868 (8) | 0.070 (3) | 0.729 (12) |
H18A | 0.5659 | 0.6254 | 0.3893 | 0.084* | 0.729 (12) |
H18B | 0.4200 | 0.7054 | 0.4356 | 0.084* | 0.729 (12) |
C19 | 0.2509 (13) | 0.5829 (7) | 0.4479 (7) | 0.063 (3) | 0.729 (12) |
C20 | 0.2881 (15) | 0.4932 (7) | 0.4377 (8) | 0.065 (3) | 0.729 (12) |
H20 | 0.4061 | 0.4732 | 0.3928 | 0.078* | 0.729 (12) |
C21 | 0.0769 (17) | 0.6103 (8) | 0.5129 (10) | 0.063 (3) | 0.729 (12) |
H21 | 0.0479 | 0.6717 | 0.5202 | 0.076* | 0.729 (12) |
C22 | 0.154 (2) | 0.4300 (8) | 0.4927 (10) | 0.085 (3) | 0.729 (12) |
H22 | 0.1837 | 0.3686 | 0.4852 | 0.102* | 0.729 (12) |
C23 | −0.024 (2) | 0.4599 (14) | 0.5590 (11) | 0.065 (6) | 0.729 (12) |
C24 | −0.059 (2) | 0.5493 (11) | 0.5684 (12) | 0.060 (4) | 0.729 (12) |
H24 | −0.1759 | 0.5704 | 0.6130 | 0.072* | 0.729 (12) |
O25 | −0.156 (4) | 0.389 (2) | 0.6129 (17) | 0.079 (6) | 0.729 (12) |
H25 | −0.24 (2) | 0.420 (8) | 0.669 (14) | 0.119* | 0.729 (12) |
C15A | 0.526 (5) | 0.7305 (17) | 0.239 (2) | 0.033 (7)* | 0.271 (12) |
O16A | 0.647 (11) | 0.698 (3) | 0.164 (6) | 0.13 (2)* | 0.271 (12) |
C17A | 0.344 (5) | 0.6930 (19) | 0.317 (3) | 0.055 (8)* | 0.271 (12) |
H17C | 0.3841 | 0.7156 | 0.4029 | 0.066* | 0.271 (12) |
H17D | 0.1770 | 0.7116 | 0.2813 | 0.066* | 0.271 (12) |
C18A | 0.363 (4) | 0.5920 (18) | 0.317 (2) | 0.075 (8)* | 0.271 (12) |
H18C | 0.5348 | 0.5749 | 0.3420 | 0.090* | 0.271 (12) |
H18D | 0.3055 | 0.5702 | 0.2321 | 0.090* | 0.271 (12) |
C19A | 0.215 (3) | 0.5467 (15) | 0.4037 (16) | 0.044 (7)* | 0.271 (12) |
C20A | 0.256 (4) | 0.4531 (14) | 0.412 (2) | 0.045* | 0.271 (12) |
H20A | 0.3644 | 0.4259 | 0.3672 | 0.054* | 0.271 (12) |
C21A | 0.054 (5) | 0.5854 (17) | 0.471 (2) | 0.050 (9)* | 0.271 (12) |
H21A | 0.0273 | 0.6474 | 0.4649 | 0.060* | 0.271 (12) |
C22A | 0.135 (5) | 0.4023 (14) | 0.487 (2) | 0.042* | 0.271 (12) |
H22A | 0.1609 | 0.3403 | 0.4942 | 0.050* | 0.271 (12) |
C23A | −0.024 (5) | 0.444 (3) | 0.553 (2) | 0.037 (12)* | 0.271 (12) |
C24A | −0.071 (6) | 0.535 (2) | 0.548 (3) | 0.071 (18)* | 0.271 (12) |
H24A | −0.1794 | 0.5619 | 0.5932 | 0.085* | 0.271 (12) |
O25A | −0.135 (10) | 0.397 (6) | 0.622 (5) | 0.061 (13)* | 0.271 (12) |
H25A | −0.18 (5) | 0.439 (15) | 0.67 (3) | 0.091* | 0.271 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.110 (3) | 0.049 (2) | 0.112 (4) | −0.013 (2) | 0.075 (3) | 0.007 (2) |
C2 | 0.060 (4) | 0.049 (3) | 0.063 (4) | 0.004 (3) | 0.027 (3) | 0.003 (3) |
C3 | 0.057 (4) | 0.034 (3) | 0.048 (4) | 0.000 (2) | 0.018 (3) | 0.007 (2) |
C4 | 0.080 (4) | 0.040 (3) | 0.097 (5) | −0.001 (3) | 0.040 (4) | 0.002 (3) |
C5 | 0.054 (4) | 0.052 (4) | 0.070 (4) | 0.000 (3) | 0.034 (3) | 0.005 (3) |
C6 | 0.063 (4) | 0.035 (3) | 0.069 (4) | 0.009 (3) | 0.039 (3) | 0.002 (3) |
C7 | 0.052 (3) | 0.037 (3) | 0.056 (4) | 0.001 (3) | 0.030 (3) | 0.002 (2) |
C8 | 0.070 (4) | 0.035 (3) | 0.079 (4) | −0.003 (3) | 0.047 (3) | 0.001 (3) |
C9 | 0.059 (4) | 0.038 (3) | 0.076 (4) | 0.004 (3) | 0.043 (3) | 0.001 (3) |
N10 | 0.069 (3) | 0.030 (2) | 0.067 (3) | 0.003 (2) | 0.046 (3) | −0.001 (2) |
C11 | 0.052 (3) | 0.044 (3) | 0.058 (4) | −0.003 (3) | 0.021 (3) | 0.001 (3) |
O12 | 0.073 (3) | 0.040 (2) | 0.088 (3) | 0.0043 (18) | 0.054 (2) | 0.0006 (19) |
C13 | 0.061 (4) | 0.037 (3) | 0.063 (4) | −0.001 (3) | 0.033 (3) | 0.000 (2) |
O14 | 0.074 (3) | 0.040 (2) | 0.098 (3) | −0.0014 (18) | 0.058 (2) | 0.0079 (19) |
C15 | 0.044 (6) | 0.046 (6) | 0.038 (6) | −0.011 (4) | −0.004 (5) | 0.017 (5) |
O16 | 0.076 (6) | 0.022 (3) | 0.148 (10) | 0.006 (3) | 0.081 (6) | 0.012 (3) |
C17 | 0.046 (5) | 0.045 (5) | 0.053 (6) | −0.006 (4) | 0.008 (4) | 0.010 (4) |
C18 | 0.070 (6) | 0.076 | 0.067 (7) | −0.017 (5) | 0.020 (5) | 0.015 (5) |
C19 | 0.054 (6) | 0.090 (7) | 0.044 (6) | −0.025 (5) | 0.009 (4) | 0.012 (5) |
C20 | 0.063 (5) | 0.064 | 0.083 (7) | −0.008 (5) | 0.052 (5) | −0.002 (6) |
C21 | 0.059 (6) | 0.081 (7) | 0.050 (7) | −0.016 (5) | 0.012 (5) | 0.014 (6) |
C22 | 0.089 (7) | 0.085 | 0.093 (8) | 0.010 (7) | 0.048 (6) | 0.002 (7) |
C23 | 0.056 (8) | 0.088 (12) | 0.057 (8) | −0.004 (6) | 0.031 (5) | 0.018 (6) |
C24 | 0.051 (7) | 0.071 (8) | 0.066 (7) | −0.005 (5) | 0.033 (5) | 0.013 (6) |
O25 | 0.085 (8) | 0.064 (9) | 0.108 (10) | −0.001 (5) | 0.068 (6) | 0.018 (6) |
O1—C2 | 1.226 (6) | C18—H18B | 0.9700 |
C2—C3 | 1.471 (7) | C19—C21 | 1.352 (13) |
C2—C4 | 1.512 (7) | C19—C20 | 1.353 (13) |
C3—C9 | 1.389 (6) | C20—C22 | 1.391 (12) |
C3—C5 | 1.398 (7) | C20—H20 | 0.9300 |
C4—H4A | 0.9600 | C21—C24 | 1.378 (13) |
C4—H4B | 0.9600 | C21—H21 | 0.9300 |
C4—H4C | 0.9600 | C22—C23 | 1.391 (13) |
C5—C6 | 1.372 (7) | C22—H22 | 0.9300 |
C5—H5 | 0.9300 | C23—C24 | 1.35 (2) |
C6—C7 | 1.380 (7) | C23—O25 | 1.46 (3) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—C8 | 1.381 (7) | O25—H25 | 0.95 (12) |
C7—N10 | 1.411 (6) | C15A—O16A | 1.24 (3) |
C8—C9 | 1.377 (7) | C15A—C17A | 1.53 (2) |
C8—H8 | 0.9300 | C17A—C18A | 1.50 (4) |
C9—H9 | 0.9300 | C17A—H17C | 0.9700 |
N10—C11 | 1.354 (6) | C17A—H17D | 0.9700 |
N10—H10 | 0.86 (5) | C18A—C19A | 1.51 (3) |
C11—O12 | 1.212 (6) | C18A—H18C | 0.9700 |
C11—C13 | 1.503 (7) | C18A—H18D | 0.9700 |
C13—O14 | 1.421 (5) | C19A—C21A | 1.37 (2) |
C13—H13A | 0.9700 | C19A—C20A | 1.41 (2) |
C13—H13B | 0.9700 | C20A—C22A | 1.37 (2) |
O14—C15A | 1.37 (3) | C20A—H20A | 0.9300 |
O14—C15 | 1.373 (11) | C21A—C24A | 1.39 (3) |
C15—O16 | 1.176 (12) | C21A—H21A | 0.9300 |
C15—C17 | 1.514 (10) | C22A—C23A | 1.38 (2) |
C17—C18 | 1.525 (13) | C22A—H22A | 0.9300 |
C17—H17A | 0.9700 | C23A—O25A | 1.26 (7) |
C17—H17B | 0.9700 | C23A—C24A | 1.37 (3) |
C18—C19 | 1.525 (11) | C24A—H24A | 0.9300 |
C18—H18A | 0.9700 | O25A—H25A | 0.90 (3) |
O1—C2—C3 | 120.8 (5) | H18A—C18—H18B | 107.7 |
O1—C2—C4 | 119.3 (5) | C21—C19—C20 | 118.0 (8) |
C3—C2—C4 | 119.9 (5) | C21—C19—C18 | 121.9 (9) |
C9—C3—C5 | 117.6 (4) | C20—C19—C18 | 120.1 (9) |
C9—C3—C2 | 123.7 (4) | C19—C20—C22 | 121.7 (8) |
C5—C3—C2 | 118.7 (5) | C19—C20—H20 | 119.2 |
C2—C4—H4A | 109.5 | C22—C20—H20 | 119.2 |
C2—C4—H4B | 109.5 | C19—C21—C24 | 121.7 (12) |
H4A—C4—H4B | 109.5 | C19—C21—H21 | 119.2 |
C2—C4—H4C | 109.5 | C24—C21—H21 | 119.2 |
H4A—C4—H4C | 109.5 | C20—C22—C23 | 119.2 (11) |
H4B—C4—H4C | 109.5 | C20—C22—H22 | 120.4 |
C6—C5—C3 | 120.6 (5) | C23—C22—H22 | 120.4 |
C6—C5—H5 | 119.7 | C24—C23—C22 | 118.5 (12) |
C3—C5—H5 | 119.7 | C24—C23—O25 | 126.0 (17) |
C5—C6—C7 | 120.8 (5) | C22—C23—O25 | 115.6 (19) |
C5—C6—H6 | 119.6 | C23—C24—C21 | 121.0 (12) |
C7—C6—H6 | 119.6 | C23—C24—H24 | 119.5 |
C6—C7—C8 | 119.5 (4) | C21—C24—H24 | 119.5 |
C6—C7—N10 | 116.5 (4) | C23—O25—H25 | 105 (8) |
C8—C7—N10 | 124.0 (4) | O16A—C15A—O14 | 113 (3) |
C9—C8—C7 | 119.6 (5) | O16A—C15A—C17A | 135 (3) |
C9—C8—H8 | 120.2 | O14—C15A—C17A | 105.6 (19) |
C7—C8—H8 | 120.2 | C18A—C17A—C15A | 108 (2) |
C8—C9—C3 | 121.8 (5) | C18A—C17A—H17C | 110.1 |
C8—C9—H9 | 119.1 | C15A—C17A—H17C | 110.1 |
C3—C9—H9 | 119.1 | C18A—C17A—H17D | 110.1 |
C11—N10—C7 | 130.0 (4) | C15A—C17A—H17D | 110.1 |
C11—N10—H10 | 118 (4) | H17C—C17A—H17D | 108.4 |
C7—N10—H10 | 112 (4) | C17A—C18A—C19A | 113 (2) |
O12—C11—N10 | 125.0 (5) | C17A—C18A—H18C | 108.9 |
O12—C11—C13 | 123.6 (5) | C19A—C18A—H18C | 108.9 |
N10—C11—C13 | 111.4 (4) | C17A—C18A—H18D | 108.9 |
O14—C13—C11 | 109.0 (4) | C19A—C18A—H18D | 108.9 |
O14—C13—H13A | 109.9 | H18C—C18A—H18D | 107.7 |
C11—C13—H13A | 109.9 | C21A—C19A—C20A | 119 (2) |
O14—C13—H13B | 109.9 | C21A—C19A—C18A | 128 (2) |
C11—C13—H13B | 109.9 | C20A—C19A—C18A | 112.3 (19) |
H13A—C13—H13B | 108.3 | C22A—C20A—C19A | 119 (2) |
C15A—O14—C13 | 113.9 (10) | C22A—C20A—H20A | 120.3 |
C15—O14—C13 | 114.3 (5) | C19A—C20A—H20A | 120.3 |
O16—C15—O14 | 122.3 (8) | C19A—C21A—C24A | 122 (2) |
O16—C15—C17 | 123.7 (9) | C19A—C21A—H21A | 118.8 |
O14—C15—C17 | 112.7 (8) | C24A—C21A—H21A | 118.8 |
C15—C17—C18 | 110.2 (7) | C20A—C22A—C23A | 119 (2) |
C15—C17—H17A | 109.6 | C20A—C22A—H22A | 120.5 |
C18—C17—H17A | 109.6 | C23A—C22A—H22A | 120.5 |
C15—C17—H17B | 109.6 | O25A—C23A—C24A | 117 (5) |
C18—C17—H17B | 109.6 | O25A—C23A—C22A | 119 (5) |
H17A—C17—H17B | 108.1 | C24A—C23A—C22A | 124 (3) |
C19—C18—C17 | 113.5 (5) | C23A—C24A—C21A | 116 (3) |
C19—C18—H18A | 108.9 | C23A—C24A—H24A | 122.0 |
C17—C18—H18A | 108.9 | C21A—C24A—H24A | 122.0 |
C19—C18—H18B | 108.9 | C23A—O25A—H25A | 103 (10) |
C17—C18—H18B | 108.9 | ||
O1—C2—C3—C9 | −179.6 (5) | C17—C18—C19—C20 | 88.3 (8) |
C4—C2—C3—C9 | 0.7 (8) | C21—C19—C20—C22 | −0.5 (5) |
O1—C2—C3—C5 | −0.9 (9) | C18—C19—C20—C22 | 179.7 (3) |
C4—C2—C3—C5 | 179.3 (5) | C20—C19—C21—C24 | 0.5 (8) |
C9—C3—C5—C6 | 0.5 (8) | C18—C19—C21—C24 | −179.7 (5) |
C2—C3—C5—C6 | −178.2 (5) | C19—C20—C22—C23 | 0.6 (7) |
C3—C5—C6—C7 | 0.9 (8) | C20—C22—C23—C24 | −0.6 (9) |
C5—C6—C7—C8 | −1.5 (9) | C20—C22—C23—O25 | 179.7 (5) |
C5—C6—C7—N10 | 179.1 (5) | C22—C23—C24—C21 | 0.6 (10) |
C6—C7—C8—C9 | 0.7 (9) | O25—C23—C24—C21 | −179.7 (6) |
N10—C7—C8—C9 | 180.0 (5) | C19—C21—C24—C23 | −0.6 (10) |
C7—C8—C9—C3 | 0.8 (9) | C15—O14—C15A—O16A | 60 (4) |
C5—C3—C9—C8 | −1.3 (8) | C13—O14—C15A—O16A | −36 (4) |
C2—C3—C9—C8 | 177.3 (6) | C15—O14—C15A—C17A | −96 (3) |
C6—C7—N10—C11 | −179.6 (5) | C13—O14—C15A—C17A | 167.6 (15) |
C8—C7—N10—C11 | 1.0 (10) | O16A—C15A—C17A—C18A | 14 (7) |
C7—N10—C11—O12 | 2.6 (10) | O14—C15A—C17A—C18A | 162 (2) |
C7—N10—C11—C13 | −176.3 (5) | C15A—C17A—C18A—C19A | 173.0 (16) |
O12—C11—C13—O14 | 2.7 (7) | C17A—C18A—C19A—C21A | 6 (2) |
N10—C11—C13—O14 | −178.4 (5) | C17A—C18A—C19A—C20A | −174 (2) |
C11—C13—O14—C15A | −158.1 (12) | C21A—C19A—C20A—C22A | −0.1 (5) |
C11—C13—O14—C15 | 175.5 (7) | C18A—C19A—C20A—C22A | 179.9 (4) |
C15A—O14—C15—O16 | −85 (3) | C20A—C19A—C21A—C24A | 0.0 (8) |
C13—O14—C15—O16 | 9.0 (15) | C18A—C19A—C21A—C24A | −180.0 (5) |
C15A—O14—C15—C17 | 82 (3) | C19A—C20A—C22A—C23A | 0.1 (8) |
C13—O14—C15—C17 | 176.8 (6) | C20A—C22A—C23A—O25A | 179.9 (6) |
O16—C15—C17—C18 | 80.5 (15) | C20A—C22A—C23A—C24A | −0.1 (11) |
O14—C15—C17—C18 | −87.2 (10) | O25A—C23A—C24A—C21A | −179.9 (7) |
C15—C17—C18—C19 | −170.4 (8) | C22A—C23A—C24A—C21A | 0.1 (11) |
C17—C18—C19—C21 | −91.5 (8) | C19A—C21A—C24A—C23A | −0.1 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10···O1i | 0.86 (5) | 2.11 (5) | 2.925 (5) | 159 (4) |
O25—H25···O12ii | 0.95 (12) | 1.93 (11) | 2.87 (3) | 172 (13) |
C4—H4A···O16iii | 0.96 | 2.59 | 3.416 (10) | 144 |
C13—H13B···O25iv | 0.97 | 2.60 | 3.458 (17) | 147 |
C13—H13B···O25Aiv | 0.97 | 2.50 | 3.34 (4) | 145 |
C24—H24···O12ii | 0.93 | 2.57 | 3.284 (11) | 133 |
Symmetry codes: (i) −x+2, y−1/2, −z; (ii) −x, y−1/2, −z+1; (iii) x, y+1, z; (iv) −x+1, y+1/2, −z+1. |
Acknowledgements
This work was supported by the research fund of Chungnam National University.
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