organic compounds
1-Hydroxy-3,4-dimethoxy-10-methylacridin-9-one
aLaboratory of Synthesis and Drug Delivery, Center of Applied Biological and Social Sciences, State University of Paraiba-Campus V; 58071-160, João Pessoa, Paraiba, Brazil, bLaboratory of Medicinal Chemistry, Departament of Organic Chemistry, Faculty of Sciences, University of Yaounde I; POBOX 812, Yaounde, Cameroon, and cDepartamento de Física e Informática, Instituto de Física de São Carlos, Universidade de São Paulo - USP, 13560-970 - São Carlos, SP, Brazil
*Correspondence e-mail: casimone@ifsc.usp.br
There are two independent molecules in the 16H15NO4, which was isolated from fruits of Zanthoxylum leprieurii. The atoms of the three rings of each molecule are close to coplanar with the largest deviations from the least-squares planes being 0.084 (3) Å and 0.069 (2) Å. Each molecule features an intramolecular O—H⋯·O hydrogen bond. In the crystal, C—H⋯·O hydrogen-bonding interactions link the molecules into a three-dimensional network.
of the title compound, CKeywords: crystal structure; Zanthoxylum leprieurii; acridone derivative.
CCDC reference: 2018018
Structure description
Zanthoxyllum leprieurii is one of the 549 species of the Zanthoxyllum genus (Rutaceae). It is widely distributed in tropical Africa (Wansi et al., 2016), and is used in traditional medicine for the treatment of anaemia, arthritis, rheumatism, pain, leprosy, HIV, malaria, stomach problems and urinary diseases, as well as having vermifuge, diuretic and laxative properties (Guetchueng et al., 2017). Its anticancer, antimicrobial, antiplasmodial and antioxidant activities have also recently been well studied (Misra et al., 2013). For its biological activity, see: Lamorde et al., (2010); Ngane et al., (2000). For related structures, see: Baudouin et al. (1985); Tchinda et al., (2009).
One of the most important et al., 2010), of which we can highlight 1-hydroxy-3,4-dimethoxy-N-methylacridone, which was first described by Baudouin et al. (1985) and has been isolated and evaluated for its bioactive potential in a single or synergistic action with other natural constituents (Baudouin et al., 1985). For background to 1-hydroxy-3,4-dimethoxy-N-methyl-acridone, see: Ladino & Suárez (2010). In this work, we describe the of the title compound, isolated from Z. leprieurii.
described in Z. leprieurii are acridone derivatives (NgoumfoThere are two independent molecules in the . The atoms of the three rings of the molecule are close to coplanar, the largest deviations from their least-square planes being exhibited by atoms C12 [0.084 (3) Å] and C26 [0.069 (2) Å]. Atoms O1, O2, O3 and C16 lie close to the mean least-squares plane of the ring system with deviations of 0.068 (2), 0.053 (2), 0.067 (2) and 0.102 (2) Å, respectively [O5 −0.082 (1), O6 0.013 (2), O7 −0.120 (2), C32 0.033 (3) Å in the second independent molecule]. Atoms C14 and C15 are −0.502 (2) and 1.374 (2) Å, respectively, out of the ring-system plane. The deviations for the second molecule are 0.440 (2) for C30 and −1.409 (2) Å for C31. The outer rings make dihedral angles of 3.26 (8) and 2.46 (7) ° with the central ring in the first molecule [2.84 (5) and 1.53 (4)° in the second.
of the title compound, as shown in Fig. 1In the crystal molecules are linked by weak C—H⋯O interactions (Table 1).
Synthesis and crystallization
The powder obtained after the pulverization of the plant material was soaked in a mixture of methylene chloride and methanol. The crude extract was subjected to
on a silica gel column eluted with an increasing polarity of ethyl acetate in hexane. The title compound, red in colour, soluble in acetone was obtained from fractions 111–120 (90 mg) by recrystallization from hexane/ethyl acetate 80/20 solution. The solvent used for single-crystal formation was absolute ethanol.Spectroscopic data the title compound are in agreement with literature data (Baudouin et al., 1985).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 2018018
https://doi.org/10.1107/S2414314620010056/ex4002sup1.cif
contains datablocks I, default. DOI:Supporting information file. DOI: https://doi.org/10.1107/S2414314620010056/ex4002Isup2.cml
Data collection: COLLECT (Nonius, 1997); cell
HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).C16H15NO4 | Z = 4 |
Mr = 285.29 | F(000) = 600 |
Triclinic, P1 | Dx = 1.420 Mg m−3 |
a = 8.3360 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.1780 (3) Å | Cell parameters from 11197 reflections |
c = 16.3260 (4) Å | θ = 2.6–27.5° |
α = 82.284 (2)° | µ = 0.10 mm−1 |
β = 76.557 (2)° | T = 293 K |
γ = 87.081 (2)° | Prism, colourless |
V = 1334.73 (6) Å3 | 0.36 × 0.23 × 0.15 mm |
Nonius KappaCCD diffractometer | 4671 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | Rint = 0.022 |
Horizonally mounted graphite crystal monochromator | θmax = 27.5°, θmin = 3.1° |
Detector resolution: 9 pixels mm-1 | h = −10→10 |
CCD rotation images,thick slices scans | k = −13→12 |
19726 measured reflections | l = −18→21 |
6073 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.184 | w = 1/[σ2(Fo2) + (0.1054P)2 + 0.3107P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
6073 reflections | Δρmax = 0.44 e Å−3 |
380 parameters | Δρmin = −0.40 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. |
Refinement. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (rings) or C—H = 0.96 Å (methyl snd hydroxy) with Uiso(H) = 1.2Ueq(C). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.34832 (15) | 0.29142 (11) | 0.15710 (8) | 0.0453 (3) | |
O2 | 0.64583 (16) | 0.21124 (12) | 0.09702 (9) | 0.0515 (3) | |
O3 | 0.84531 (15) | 0.65229 (13) | 0.03086 (9) | 0.0523 (3) | |
O4 | 0.64390 (16) | 0.83835 (12) | 0.05781 (9) | 0.0545 (3) | |
O5 | 0.27751 (16) | 0.74356 (12) | 0.61638 (8) | 0.0490 (3) | |
O6 | 0.19210 (18) | 0.86749 (12) | 0.48348 (9) | 0.0535 (3) | |
O7 | 0.14839 (19) | 0.46740 (13) | 0.37138 (8) | 0.0563 (4) | |
O8 | 0.2317 (2) | 0.25560 (13) | 0.44761 (9) | 0.0576 (4) | |
N1 | 0.26613 (16) | 0.57543 (13) | 0.14686 (8) | 0.0371 (3) | |
N2 | 0.34120 (17) | 0.45683 (13) | 0.62919 (9) | 0.0396 (3) | |
C1 | 0.2369 (2) | 0.71041 (16) | 0.15183 (10) | 0.0390 (4) | |
C2 | 0.3625 (2) | 0.80256 (16) | 0.11976 (10) | 0.0398 (4) | |
C3 | 0.5293 (2) | 0.75708 (16) | 0.08543 (10) | 0.0384 (3) | |
C4 | 0.55708 (18) | 0.61589 (15) | 0.08865 (9) | 0.0343 (3) | |
C5 | 0.42538 (18) | 0.52538 (15) | 0.12017 (9) | 0.0329 (3) | |
C6 | 0.46427 (19) | 0.38806 (15) | 0.12420 (10) | 0.0356 (3) | |
C7 | 0.6265 (2) | 0.34534 (16) | 0.09288 (10) | 0.0385 (3) | |
C8 | 0.7552 (2) | 0.43262 (17) | 0.06184 (11) | 0.0413 (4) | |
H8 | 0.8624 | 0.4015 | 0.0425 | 0.050* | |
C9 | 0.72055 (19) | 0.56693 (16) | 0.06034 (10) | 0.0383 (3) | |
C10 | 0.3281 (2) | 0.93932 (18) | 0.12005 (13) | 0.0508 (4) | |
H10 | 0.4120 | 0.9996 | 0.0974 | 0.061* | |
C11 | 0.1715 (3) | 0.9843 (2) | 0.15353 (15) | 0.0614 (5) | |
H11 | 0.1481 | 1.0747 | 0.1525 | 0.074* | |
C12 | 0.0491 (3) | 0.8930 (2) | 0.18875 (16) | 0.0641 (6) | |
H12 | −0.0561 | 0.9233 | 0.2132 | 0.077* | |
C13 | 0.0781 (2) | 0.7589 (2) | 0.18874 (13) | 0.0538 (5) | |
H13 | −0.0066 | 0.7000 | 0.2130 | 0.065* | |
C14 | 0.1194 (2) | 0.49385 (19) | 0.15926 (13) | 0.0494 (4) | |
H14A | 0.0218 | 0.5462 | 0.1777 | 0.074* | |
H14B | 0.1163 | 0.4627 | 0.1067 | 0.074* | |
H14C | 0.1245 | 0.4194 | 0.2015 | 0.074* | |
C15 | 0.3563 (3) | 0.2314 (2) | 0.24026 (12) | 0.0567 (5) | |
H15A | 0.2732 | 0.1653 | 0.2599 | 0.085* | |
H15B | 0.4632 | 0.1907 | 0.2387 | 0.085* | |
H15C | 0.3378 | 0.2979 | 0.2781 | 0.085* | |
C16 | 0.8075 (3) | 0.1570 (2) | 0.06854 (15) | 0.0583 (5) | |
H16A | 0.8029 | 0.0620 | 0.0751 | 0.087* | |
H16B | 0.8493 | 0.1896 | 0.0098 | 0.087* | |
H16C | 0.8791 | 0.1829 | 0.1016 | 0.087* | |
C17 | 0.28342 (19) | 0.52898 (15) | 0.56263 (10) | 0.0360 (3) | |
C18 | 0.2465 (2) | 0.45975 (15) | 0.49895 (10) | 0.0375 (3) | |
C19 | 0.2651 (2) | 0.31822 (16) | 0.50310 (11) | 0.0418 (4) | |
C20 | 0.3209 (2) | 0.24810 (16) | 0.57486 (11) | 0.0403 (4) | |
C21 | 0.3513 (2) | 0.31925 (16) | 0.63754 (10) | 0.0389 (3) | |
C22 | 0.2578 (2) | 0.66750 (16) | 0.55527 (10) | 0.0394 (4) | |
C23 | 0.2074 (2) | 0.73401 (16) | 0.48463 (11) | 0.0425 (4) | |
C24 | 0.1726 (2) | 0.66747 (18) | 0.42197 (11) | 0.0461 (4) | |
H24 | 0.1396 | 0.7139 | 0.3754 | 0.055* | |
C25 | 0.1881 (2) | 0.53179 (17) | 0.43046 (11) | 0.0422 (4) | |
C26 | 0.3953 (3) | 0.24636 (19) | 0.70890 (12) | 0.0522 (4) | |
H26 | 0.4102 | 0.2903 | 0.7529 | 0.063* | |
C27 | 0.4164 (3) | 0.1110 (2) | 0.71424 (14) | 0.0600 (5) | |
H27 | 0.4455 | 0.0647 | 0.7619 | 0.072* | |
C28 | 0.3953 (3) | 0.04215 (19) | 0.64993 (15) | 0.0587 (5) | |
H28 | 0.4147 | −0.0490 | 0.6531 | 0.070* | |
C29 | 0.3454 (2) | 0.11009 (18) | 0.58159 (13) | 0.0500 (4) | |
H29 | 0.3276 | 0.0641 | 0.5391 | 0.060* | |
C30 | 0.4188 (3) | 0.5227 (2) | 0.68466 (13) | 0.0562 (5) | |
H30A | 0.4042 | 0.6170 | 0.6733 | 0.084* | |
H30B | 0.3684 | 0.4935 | 0.7430 | 0.084* | |
H30C | 0.5345 | 0.5005 | 0.6738 | 0.084* | |
C31 | 0.1259 (3) | 0.7728 (2) | 0.67321 (14) | 0.0658 (6) | |
H31A | 0.1471 | 0.8255 | 0.7139 | 0.099* | |
H31B | 0.0530 | 0.8210 | 0.6417 | 0.099* | |
H31C | 0.0755 | 0.6915 | 0.7022 | 0.099* | |
C32 | 0.1415 (3) | 0.94238 (19) | 0.41295 (15) | 0.0621 (5) | |
H32A | 0.1355 | 1.0349 | 0.4197 | 0.093* | |
H32B | 0.2201 | 0.9287 | 0.3614 | 0.093* | |
H32C | 0.0351 | 0.9139 | 0.4103 | 0.093* | |
H1 | 0.7961 | 0.7434 | 0.0350 | 0.094 (6)* | |
H2 | 0.1696 | 0.3765 | 0.3915 | 0.094 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0453 (7) | 0.0403 (6) | 0.0503 (7) | −0.0098 (5) | −0.0123 (5) | −0.0002 (5) |
O2 | 0.0498 (7) | 0.0375 (6) | 0.0649 (8) | 0.0037 (5) | −0.0077 (6) | −0.0100 (6) |
O3 | 0.0331 (6) | 0.0481 (7) | 0.0706 (9) | −0.0067 (5) | −0.0031 (6) | −0.0028 (6) |
O4 | 0.0450 (7) | 0.0406 (6) | 0.0731 (9) | −0.0082 (5) | −0.0079 (6) | 0.0031 (6) |
O5 | 0.0582 (8) | 0.0420 (6) | 0.0514 (7) | −0.0085 (5) | −0.0129 (6) | −0.0182 (5) |
O6 | 0.0693 (9) | 0.0340 (6) | 0.0591 (8) | −0.0027 (6) | −0.0186 (6) | −0.0044 (5) |
O7 | 0.0781 (9) | 0.0519 (7) | 0.0504 (7) | 0.0021 (6) | −0.0344 (7) | −0.0144 (6) |
O8 | 0.0878 (10) | 0.0419 (7) | 0.0548 (8) | −0.0002 (6) | −0.0334 (7) | −0.0177 (6) |
N1 | 0.0306 (6) | 0.0409 (7) | 0.0388 (7) | −0.0026 (5) | −0.0078 (5) | −0.0009 (5) |
N2 | 0.0459 (8) | 0.0390 (7) | 0.0380 (7) | −0.0055 (6) | −0.0149 (6) | −0.0085 (5) |
C1 | 0.0374 (8) | 0.0434 (8) | 0.0370 (8) | 0.0038 (6) | −0.0117 (6) | −0.0043 (6) |
C2 | 0.0404 (8) | 0.0395 (8) | 0.0412 (8) | 0.0028 (6) | −0.0153 (7) | −0.0024 (6) |
C3 | 0.0383 (8) | 0.0394 (8) | 0.0376 (8) | −0.0021 (6) | −0.0119 (6) | 0.0010 (6) |
C4 | 0.0337 (7) | 0.0385 (8) | 0.0312 (7) | −0.0013 (6) | −0.0109 (6) | −0.0002 (6) |
C5 | 0.0322 (7) | 0.0392 (8) | 0.0283 (7) | −0.0010 (6) | −0.0101 (6) | −0.0019 (6) |
C6 | 0.0363 (8) | 0.0372 (8) | 0.0341 (7) | −0.0046 (6) | −0.0101 (6) | −0.0018 (6) |
C7 | 0.0424 (8) | 0.0379 (8) | 0.0372 (8) | 0.0029 (6) | −0.0126 (7) | −0.0064 (6) |
C8 | 0.0334 (8) | 0.0471 (9) | 0.0430 (9) | 0.0029 (7) | −0.0084 (6) | −0.0063 (7) |
C9 | 0.0322 (7) | 0.0443 (8) | 0.0378 (8) | −0.0033 (6) | −0.0082 (6) | −0.0026 (6) |
C10 | 0.0532 (10) | 0.0410 (9) | 0.0624 (11) | 0.0042 (7) | −0.0237 (9) | −0.0045 (8) |
C11 | 0.0575 (12) | 0.0487 (10) | 0.0840 (15) | 0.0164 (9) | −0.0267 (11) | −0.0177 (10) |
C12 | 0.0476 (11) | 0.0653 (13) | 0.0804 (14) | 0.0181 (9) | −0.0140 (10) | −0.0214 (11) |
C13 | 0.0393 (9) | 0.0592 (11) | 0.0614 (11) | 0.0042 (8) | −0.0078 (8) | −0.0106 (9) |
C14 | 0.0335 (8) | 0.0531 (10) | 0.0605 (11) | −0.0079 (7) | −0.0105 (7) | −0.0011 (8) |
C15 | 0.0694 (13) | 0.0494 (10) | 0.0464 (10) | −0.0116 (9) | −0.0058 (9) | 0.0018 (8) |
C16 | 0.0537 (11) | 0.0490 (10) | 0.0731 (13) | 0.0145 (8) | −0.0156 (10) | −0.0147 (9) |
C17 | 0.0356 (8) | 0.0378 (8) | 0.0353 (8) | −0.0056 (6) | −0.0069 (6) | −0.0072 (6) |
C18 | 0.0398 (8) | 0.0375 (8) | 0.0373 (8) | −0.0032 (6) | −0.0099 (6) | −0.0096 (6) |
C19 | 0.0465 (9) | 0.0404 (8) | 0.0418 (8) | −0.0040 (7) | −0.0123 (7) | −0.0116 (7) |
C20 | 0.0391 (8) | 0.0390 (8) | 0.0447 (9) | −0.0030 (6) | −0.0111 (7) | −0.0081 (7) |
C21 | 0.0364 (8) | 0.0403 (8) | 0.0413 (8) | −0.0038 (6) | −0.0098 (6) | −0.0070 (7) |
C22 | 0.0423 (8) | 0.0363 (8) | 0.0413 (8) | −0.0071 (6) | −0.0087 (7) | −0.0104 (6) |
C23 | 0.0429 (9) | 0.0359 (8) | 0.0482 (9) | −0.0041 (6) | −0.0080 (7) | −0.0067 (7) |
C24 | 0.0517 (10) | 0.0442 (9) | 0.0443 (9) | −0.0001 (7) | −0.0159 (8) | −0.0037 (7) |
C25 | 0.0461 (9) | 0.0445 (9) | 0.0397 (8) | −0.0015 (7) | −0.0140 (7) | −0.0113 (7) |
C26 | 0.0618 (11) | 0.0513 (10) | 0.0489 (10) | −0.0043 (8) | −0.0242 (9) | −0.0039 (8) |
C27 | 0.0666 (13) | 0.0526 (11) | 0.0653 (12) | −0.0021 (9) | −0.0310 (10) | 0.0046 (9) |
C28 | 0.0628 (12) | 0.0400 (9) | 0.0783 (14) | 0.0001 (8) | −0.0296 (11) | −0.0018 (9) |
C29 | 0.0521 (10) | 0.0411 (9) | 0.0627 (11) | −0.0006 (7) | −0.0213 (9) | −0.0126 (8) |
C30 | 0.0723 (13) | 0.0528 (11) | 0.0552 (11) | −0.0033 (9) | −0.0324 (10) | −0.0163 (9) |
C31 | 0.0763 (14) | 0.0600 (12) | 0.0560 (12) | −0.0111 (10) | 0.0046 (10) | −0.0200 (10) |
C32 | 0.0764 (14) | 0.0402 (9) | 0.0699 (13) | 0.0006 (9) | −0.0228 (11) | 0.0021 (9) |
O1—C6 | 1.3798 (19) | C13—H13 | 0.9300 |
O1—C15 | 1.427 (2) | C14—H14A | 0.9600 |
O2—C7 | 1.3606 (19) | C14—H14B | 0.9600 |
O2—C16 | 1.428 (2) | C14—H14C | 0.9600 |
O3—C9 | 1.347 (2) | C15—H15A | 0.9600 |
O3—H1 | 1.00 | C15—H15B | 0.9600 |
O4—C3 | 1.257 (2) | C15—H15C | 0.9600 |
O5—C22 | 1.3849 (19) | C16—H16A | 0.9600 |
O5—C31 | 1.427 (2) | C16—H16B | 0.9600 |
O6—C23 | 1.356 (2) | C16—H16C | 0.9600 |
O6—C32 | 1.429 (2) | C17—C22 | 1.408 (2) |
O7—C25 | 1.345 (2) | C17—C18 | 1.428 (2) |
O7—H2 | 0.96 | C18—C25 | 1.421 (2) |
O8—C19 | 1.263 (2) | C18—C19 | 1.435 (2) |
N1—C5 | 1.3905 (19) | C19—C20 | 1.447 (2) |
N1—C1 | 1.393 (2) | C20—C29 | 1.402 (2) |
N1—C14 | 1.473 (2) | C20—C21 | 1.405 (2) |
N2—C21 | 1.389 (2) | C21—C26 | 1.408 (2) |
N2—C17 | 1.395 (2) | C22—C23 | 1.397 (2) |
N2—C30 | 1.472 (2) | C23—C24 | 1.390 (2) |
C1—C2 | 1.401 (2) | C24—C25 | 1.372 (2) |
C1—C13 | 1.414 (2) | C24—H24 | 0.9300 |
C2—C10 | 1.407 (2) | C26—C27 | 1.374 (3) |
C2—C3 | 1.450 (2) | C26—H26 | 0.9300 |
C3—C4 | 1.440 (2) | C27—C28 | 1.386 (3) |
C4—C9 | 1.421 (2) | C27—H27 | 0.9300 |
C4—C5 | 1.425 (2) | C28—C29 | 1.369 (3) |
C5—C6 | 1.415 (2) | C28—H28 | 0.9300 |
C6—C7 | 1.399 (2) | C29—H29 | 0.9300 |
C7—C8 | 1.386 (2) | C30—H30A | 0.9600 |
C8—C9 | 1.381 (2) | C30—H30B | 0.9600 |
C8—H8 | 0.9300 | C30—H30C | 0.9600 |
C10—C11 | 1.374 (3) | C31—H31A | 0.9600 |
C10—H10 | 0.9300 | C31—H31B | 0.9600 |
C11—C12 | 1.384 (3) | C31—H31C | 0.9600 |
C11—H11 | 0.9300 | C32—H32A | 0.9600 |
C12—C13 | 1.374 (3) | C32—H32B | 0.9600 |
C12—H12 | 0.9300 | C32—H32C | 0.9600 |
C6—O1—C15 | 113.10 (13) | O2—C16—H16A | 109.5 |
C7—O2—C16 | 118.42 (15) | O2—C16—H16B | 109.5 |
C9—O3—H1 | 106.7 | H16A—C16—H16B | 109.5 |
C22—O5—C31 | 113.22 (15) | O2—C16—H16C | 109.5 |
C23—O6—C32 | 117.70 (15) | H16A—C16—H16C | 109.5 |
C25—O7—H2 | 101.9 | H16B—C16—H16C | 109.5 |
C5—N1—C1 | 120.95 (13) | N2—C17—C22 | 123.21 (14) |
C5—N1—C14 | 122.23 (14) | N2—C17—C18 | 118.85 (14) |
C1—N1—C14 | 116.26 (13) | C22—C17—C18 | 117.94 (15) |
C21—N2—C17 | 121.03 (13) | C25—C18—C17 | 119.60 (15) |
C21—N2—C30 | 116.86 (14) | C25—C18—C19 | 119.06 (14) |
C17—N2—C30 | 121.38 (14) | C17—C18—C19 | 121.34 (15) |
N1—C1—C2 | 121.35 (14) | O8—C19—C18 | 122.04 (16) |
N1—C1—C13 | 120.78 (16) | O8—C19—C20 | 120.53 (15) |
C2—C1—C13 | 117.87 (16) | C18—C19—C20 | 117.42 (14) |
C1—C2—C10 | 120.56 (16) | C29—C20—C21 | 120.19 (16) |
C1—C2—C3 | 119.91 (15) | C29—C20—C19 | 120.23 (15) |
C10—C2—C3 | 119.53 (16) | C21—C20—C19 | 119.58 (14) |
O4—C3—C4 | 122.44 (15) | N2—C21—C20 | 121.49 (15) |
O4—C3—C2 | 120.66 (15) | N2—C21—C26 | 120.81 (15) |
C4—C3—C2 | 116.82 (14) | C20—C21—C26 | 117.69 (16) |
C9—C4—C5 | 119.82 (14) | O5—C22—C23 | 116.96 (14) |
C9—C4—C3 | 118.60 (14) | O5—C22—C17 | 123.00 (15) |
C5—C4—C3 | 121.57 (14) | C23—C22—C17 | 120.03 (14) |
N1—C5—C6 | 123.14 (14) | O6—C23—C24 | 123.22 (16) |
N1—C5—C4 | 118.88 (14) | O6—C23—C22 | 114.49 (15) |
C6—C5—C4 | 117.96 (14) | C24—C23—C22 | 122.28 (15) |
O1—C6—C7 | 117.14 (14) | C25—C24—C23 | 118.45 (16) |
O1—C6—C5 | 123.08 (14) | C25—C24—H24 | 120.8 |
C7—C6—C5 | 119.78 (14) | C23—C24—H24 | 120.8 |
O2—C7—C8 | 123.57 (15) | O7—C25—C24 | 118.28 (15) |
O2—C7—C6 | 113.88 (14) | O7—C25—C18 | 120.19 (15) |
C8—C7—C6 | 122.54 (15) | C24—C25—C18 | 121.53 (15) |
C9—C8—C7 | 118.40 (15) | C27—C26—C21 | 120.69 (17) |
C9—C8—H8 | 120.8 | C27—C26—H26 | 119.7 |
C7—C8—H8 | 120.8 | C21—C26—H26 | 119.7 |
O3—C9—C8 | 118.70 (14) | C26—C27—C28 | 121.28 (18) |
O3—C9—C4 | 119.92 (15) | C26—C27—H27 | 119.4 |
C8—C9—C4 | 121.38 (15) | C28—C27—H27 | 119.4 |
C11—C10—C2 | 120.43 (19) | C29—C28—C27 | 119.12 (18) |
C11—C10—H10 | 119.8 | C29—C28—H28 | 120.4 |
C2—C10—H10 | 119.8 | C27—C28—H28 | 120.4 |
C10—C11—C12 | 119.01 (18) | C28—C29—C20 | 120.86 (17) |
C10—C11—H11 | 120.5 | C28—C29—H29 | 119.6 |
C12—C11—H11 | 120.5 | C20—C29—H29 | 119.6 |
C13—C12—C11 | 121.98 (18) | N2—C30—H30A | 109.5 |
C13—C12—H12 | 119.0 | N2—C30—H30B | 109.5 |
C11—C12—H12 | 119.0 | H30A—C30—H30B | 109.5 |
C12—C13—C1 | 120.04 (19) | N2—C30—H30C | 109.5 |
C12—C13—H13 | 120.0 | H30A—C30—H30C | 109.5 |
C1—C13—H13 | 120.0 | H30B—C30—H30C | 109.5 |
N1—C14—H14A | 109.5 | O5—C31—H31A | 109.5 |
N1—C14—H14B | 109.5 | O5—C31—H31B | 109.5 |
H14A—C14—H14B | 109.5 | H31A—C31—H31B | 109.5 |
N1—C14—H14C | 109.5 | O5—C31—H31C | 109.5 |
H14A—C14—H14C | 109.5 | H31A—C31—H31C | 109.5 |
H14B—C14—H14C | 109.5 | H31B—C31—H31C | 109.5 |
O1—C15—H15A | 109.5 | O6—C32—H32A | 109.5 |
O1—C15—H15B | 109.5 | O6—C32—H32B | 109.5 |
H15A—C15—H15B | 109.5 | H32A—C32—H32B | 109.5 |
O1—C15—H15C | 109.5 | O6—C32—H32C | 109.5 |
H15A—C15—H15C | 109.5 | H32A—C32—H32C | 109.5 |
H15B—C15—H15C | 109.5 | H32B—C32—H32C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O3i | 0.93 | 2.52 | 3.441 (2) | 170 |
C32—H32A···O8ii | 0.96 | 2.55 | 3.460 (3) | 157 |
C30—H30C···O7iii | 0.96 | 2.59 | 3.513 (3) | 159 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, y+1, z; (iii) −x+1, −y+1, −z+1. |
Acknowledgements
The authors are grateful to the Instituto de Física de São Carlos for access to the KappaCCD diffractometer and thank the Nucleus of Analysis and Research in Nuclear Magnetic Resonance (NAPRMN–UFAL) for providing the NMR spectra.
Funding information
This work was partly supported by the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (grant No. 308590/2017–1) and was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) – Finance Code 001. ENTZ thanks the World Academy of Science/Brazilian National Council for Scientific and Technological Development (TWAS/CNPq) for the 2017 Postdoctoral Fellowship Programme attributed to PhD Ernestine Nkwengoua T. Zondegoumba. and CAS is thankful to the CNPq for a fellowship.
References
Baudouin, G., Tillequin, F., Koch, M., Dau, M. T. H., Guilhem, J., Pusset, J. & Chauviere, G. (1985). J. Nat. Prod. 48, 260–265. CSD CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Guetchueng, S. T., Nahar, L., Ritchie, K. J., Ismail, F. M., Wansi, J. D., Evans, A. R. & Sarker, S. D. (2017). Rec. Nat. Prod. 11, 304–309. CAS Google Scholar
Ladino, O. J. P. & Suárez, L. E. C. (2010). Quím. Nova, 33, 1019-1021. Google Scholar
Misra, L. N., Wouatsa, N. A. V., Kumar, S., Kumar, R. V. & Tchoumbougnang, F. (2013). J. Ethnopharmacol. 148, 74–80. Web of Science CrossRef CAS PubMed Google Scholar
Ngoumfo, R. M., Jouda, J.-B., Mouafo, F. T., Komguem, J., Mbazoa, C. D., Shiao, T. C., Choudhary, M. I., Laatsch, H., Legault, J., Pichette, A. & Roy, A. (2010). Bioorg. Med. Chem. 18, 3601–3605. Web of Science CrossRef CAS PubMed Google Scholar
Nonius (1997). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wansi, J. D., Tcho, A. T., Toze, F. A. A., Nahar, L., Martin, C. & Sarker, S. D. (2016). Phytochemistry Lett. 17, 293–298. Web of Science CrossRef CAS Google Scholar
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