organic compounds
3-(2-Hydroxy-4-methoxyphenyl)-N-(2-methoxyphenyl)-5-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
aDivision of Bioscience and Biotechnology, BMIC, Konkuk University, Seoul 143-701, Republic of Korea, and bDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
*Correspondence e-mail: dskoh@dongduk.ac.kr
In the title molecule, C28H25N3O3S, the dihedral angles formed by the naphthalene ring system and the benzene rings are 73.03 (13) and 74.04 (11)°. The benzene rings attached to the central pyrazoline ring are almost coplanar, as indicated by the dihedral angle of 2.22 (10)° between them. The C atom of the methoxy group of the phenol ring is essentially coplanar with the ring [C—C—O—C = −0.3 (3)°], whereas the C atom of the methoxy group of the thioamide benzene ring is slightly twisted [C—C—O—C = 5.4 (3)°]. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, pairs of very weak C—H⋯S interactions form inversion dimers with an R22(18) motif.
Keywords: crystal structure; pyrazoline; thioamide.
CCDC reference: 1550731
Structure description
Pyrazolines show a broad spectrum of biological activities including the dual function of antimalarial and antimicrobial (Mishra, et al., 2017), antibacterial (Viveka et al., 2015), anti-inflammatory (Kharbanda, et al., 2014) and antitumor activities (Bashir et al., 2011). In continuation of our studies of new pyrazoline derivatives which may show broad range of biological activities (Jung et al. 2015), the title compound I was synthesized and its was determined. For related structures, see: Abdel-Wahab et al. (2013); Koh et al. (2014).
The molecular structure of I is shown in Fig. 1. The benzene ring and naphthalene ring system are attached at the C1 and C3 position of central pyrazoline ring and another benzene ring is attached at N1 by a carbothioamide linkage. The dihedral angles formed by the naphthalene ring system at C3 and the benzene rings at C1 and N1 are 73.03 (13) and 74.04 (11)°, respectively. The benzene rings attached to the pyrazoline ring at C1 and N1 are almost in the same plane [dihedral angle = 2.22 (10)°]. The C atom of the methoxy group of the phenol ring is essentially co-planar with the ring [C8—C7—O2—C10 = −0.3 (3)°], whereas the C atom of the methoxy group at the thioamide benzene ring is slightly twisted from the ring plane [C24—C23—O3—C28 = 5.4 (3)°]. An intramolecular O1—H1O⋯N1 hydrogen bond forms an S(6) ring motif (Table 1). In the crystal, pairs of week C—H⋯S interactions form inversion dimers (Fig. 2).
Synthesis and crystallization
By the previously reported method (Jung et al. 2015), chalcone intermediate III was prepared and converted into pyrazoline intermediate IV via imine formation followed by Michael addition of hydrazine. The reaction between IV and isothiocyanate V gave the desired pyrazoline carbothiamide (see Fig. 3).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1550731
https://doi.org/10.1107/S2414314617007325/hb4146sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617007325/hb4146Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617007325/hb4146Isup3.cml
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C28H25N3O3S | F(000) = 1016 |
Mr = 483.57 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5750 reflections |
a = 6.8521 (4) Å | θ = 2.2–27.9° |
b = 23.1503 (13) Å | µ = 0.17 mm−1 |
c = 15.0422 (8) Å | T = 173 K |
β = 99.365 (1)° | Block, yellow |
V = 2354.3 (2) Å3 | 0.22 × 0.16 × 0.10 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 3091 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
phi and ω scans | h = −8→9 |
17230 measured reflections | k = −23→30 |
5827 independent reflections | l = −20→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0716P)2] where P = (Fo2 + 2Fc2)/3 |
5827 reflections | (Δ/σ)max = 0.001 |
319 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.24 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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6669 (2) | 0.68425 (6) | 0.92398 (10) | 0.0466 (4) | |
N2 | 0.7136 (2) | 0.74261 (6) | 0.93947 (10) | 0.0443 (4) | |
C1 | 0.8947 (3) | 0.74602 (8) | 0.98041 (11) | 0.0405 (4) | |
C2 | 0.9924 (3) | 0.68823 (7) | 0.99689 (12) | 0.0431 (4) | |
H2A | 1.0532 | 0.6837 | 1.0609 | 0.052* | |
H2B | 1.0951 | 0.6826 | 0.9584 | 0.052* | |
C3 | 0.8196 (3) | 0.64595 (8) | 0.97126 (12) | 0.0437 (5) | |
H3 | 0.8551 | 0.6155 | 0.9296 | 0.052* | |
C4 | 0.9887 (3) | 0.80096 (8) | 1.00541 (12) | 0.0406 (4) | |
C5 | 0.8889 (3) | 0.85421 (8) | 0.99168 (12) | 0.0448 (5) | |
O1 | 0.69489 (19) | 0.85814 (6) | 0.95457 (10) | 0.0583 (4) | |
H1 | 0.6497 | 0.8249 | 0.9416 | 0.087* | |
C6 | 0.9869 (3) | 0.90568 (8) | 1.01527 (13) | 0.0478 (5) | |
H6 | 0.9175 | 0.9413 | 1.0064 | 0.057* | |
C7 | 1.1853 (3) | 0.90539 (8) | 1.05168 (12) | 0.0457 (5) | |
C8 | 1.2875 (3) | 0.85359 (8) | 1.06688 (13) | 0.0490 (5) | |
H8 | 1.4235 | 0.8533 | 1.0928 | 0.059* | |
C9 | 1.1890 (3) | 0.80279 (8) | 1.04382 (12) | 0.0456 (5) | |
H9 | 1.2594 | 0.7675 | 1.0543 | 0.055* | |
O2 | 1.2692 (2) | 0.95858 (5) | 1.06886 (9) | 0.0563 (4) | |
C10 | 1.4744 (3) | 0.96092 (9) | 1.10511 (15) | 0.0614 (6) | |
H10A | 1.4972 | 0.9425 | 1.1645 | 0.092* | |
H10B | 1.5173 | 1.0013 | 1.1109 | 0.092* | |
H10C | 1.5500 | 0.9406 | 1.0648 | 0.092* | |
C11 | 0.7552 (3) | 0.61868 (8) | 1.05338 (13) | 0.0477 (5) | |
C12 | 0.5914 (3) | 0.63734 (10) | 1.08515 (15) | 0.0646 (6) | |
H12 | 0.5114 | 0.6666 | 1.0533 | 0.078* | |
C13 | 0.5384 (4) | 0.61442 (16) | 1.1636 (2) | 0.1038 (11) | |
H13 | 0.4251 | 0.6287 | 1.1855 | 0.125* | |
C14 | 0.6474 (5) | 0.57218 (16) | 1.2083 (2) | 0.1130 (12) | |
H14 | 0.6082 | 0.5565 | 1.2611 | 0.136* | |
C15 | 0.8173 (4) | 0.55059 (11) | 1.17942 (17) | 0.0820 (9) | |
C16 | 0.8761 (3) | 0.57470 (8) | 1.10030 (14) | 0.0574 (6) | |
C17 | 1.0517 (4) | 0.55469 (8) | 1.07327 (16) | 0.0678 (7) | |
H17 | 1.0942 | 0.5709 | 1.0217 | 0.081* | |
C18 | 1.1624 (5) | 0.51184 (10) | 1.1209 (2) | 0.0945 (10) | |
H18 | 1.2799 | 0.4984 | 1.1018 | 0.113* | |
C19 | 1.1014 (6) | 0.48799 (11) | 1.1980 (2) | 0.1073 (14) | |
H19 | 1.1788 | 0.4588 | 1.2312 | 0.129* | |
C20 | 0.9358 (6) | 0.50619 (14) | 1.2246 (2) | 0.1161 (14) | |
H20 | 0.8958 | 0.4887 | 1.2759 | 0.139* | |
C21 | 0.4949 (3) | 0.66760 (9) | 0.87116 (12) | 0.0486 (5) | |
S1 | 0.43887 (9) | 0.59834 (2) | 0.85550 (4) | 0.0700 (2) | |
N3 | 0.3851 (2) | 0.71315 (7) | 0.83677 (11) | 0.0572 (5) | |
H3A | 0.4489 | 0.7463 | 0.8429 | 0.069* | |
C22 | 0.1887 (3) | 0.71777 (9) | 0.79305 (12) | 0.0484 (5) | |
C23 | 0.1202 (3) | 0.77489 (9) | 0.78290 (12) | 0.0491 (5) | |
C24 | −0.0711 (3) | 0.78644 (9) | 0.74395 (13) | 0.0547 (5) | |
H24 | −0.1168 | 0.8252 | 0.7370 | 0.066* | |
C25 | −0.1979 (3) | 0.74061 (10) | 0.71471 (14) | 0.0604 (6) | |
H25 | −0.3308 | 0.7482 | 0.6880 | 0.073* | |
C26 | −0.1321 (3) | 0.68513 (10) | 0.72435 (13) | 0.0584 (6) | |
H26 | −0.2202 | 0.6543 | 0.7046 | 0.070* | |
C27 | 0.0604 (3) | 0.67287 (9) | 0.76234 (13) | 0.0550 (5) | |
H27 | 0.1051 | 0.6340 | 0.7675 | 0.066* | |
O3 | 0.2590 (2) | 0.81574 (6) | 0.81542 (9) | 0.0614 (4) | |
C28 | 0.1973 (3) | 0.87432 (9) | 0.81590 (14) | 0.0618 (6) | |
H28A | 0.1587 | 0.8878 | 0.7538 | 0.093* | |
H28B | 0.3065 | 0.8981 | 0.8463 | 0.093* | |
H28C | 0.0843 | 0.8775 | 0.8480 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0468 (10) | 0.0413 (9) | 0.0474 (9) | −0.0097 (7) | −0.0052 (7) | 0.0015 (7) |
N2 | 0.0457 (10) | 0.0427 (9) | 0.0416 (8) | −0.0089 (7) | −0.0018 (7) | 0.0023 (7) |
C1 | 0.0398 (11) | 0.0484 (11) | 0.0330 (9) | −0.0060 (8) | 0.0049 (8) | −0.0007 (8) |
C2 | 0.0391 (11) | 0.0472 (11) | 0.0425 (10) | −0.0044 (8) | 0.0052 (8) | −0.0030 (8) |
C3 | 0.0443 (12) | 0.0426 (10) | 0.0416 (10) | −0.0029 (8) | −0.0011 (8) | −0.0047 (8) |
C4 | 0.0375 (10) | 0.0453 (11) | 0.0390 (9) | −0.0053 (8) | 0.0062 (8) | 0.0010 (8) |
C5 | 0.0374 (11) | 0.0499 (11) | 0.0462 (11) | −0.0061 (8) | 0.0045 (8) | −0.0007 (9) |
O1 | 0.0385 (8) | 0.0512 (8) | 0.0806 (10) | −0.0040 (6) | −0.0037 (7) | −0.0002 (8) |
C6 | 0.0466 (12) | 0.0451 (11) | 0.0511 (11) | −0.0032 (8) | 0.0060 (9) | −0.0033 (9) |
C7 | 0.0474 (12) | 0.0442 (11) | 0.0455 (11) | −0.0113 (8) | 0.0072 (9) | −0.0056 (8) |
C8 | 0.0390 (11) | 0.0533 (12) | 0.0517 (11) | −0.0077 (9) | −0.0016 (9) | −0.0039 (9) |
C9 | 0.0418 (11) | 0.0448 (11) | 0.0485 (11) | −0.0020 (8) | 0.0028 (8) | −0.0011 (8) |
O2 | 0.0505 (9) | 0.0485 (8) | 0.0671 (9) | −0.0129 (6) | 0.0012 (7) | −0.0081 (7) |
C10 | 0.0521 (14) | 0.0600 (13) | 0.0706 (14) | −0.0201 (10) | 0.0055 (11) | −0.0133 (11) |
C11 | 0.0416 (11) | 0.0451 (11) | 0.0510 (11) | −0.0138 (9) | −0.0082 (9) | 0.0026 (9) |
C12 | 0.0386 (13) | 0.0925 (17) | 0.0606 (14) | −0.0154 (11) | 0.0019 (10) | 0.0154 (12) |
C13 | 0.0488 (16) | 0.177 (3) | 0.0843 (19) | −0.0222 (18) | 0.0083 (14) | 0.044 (2) |
C14 | 0.068 (2) | 0.168 (3) | 0.097 (2) | −0.049 (2) | −0.0050 (17) | 0.068 (2) |
C15 | 0.0709 (18) | 0.0750 (17) | 0.0855 (18) | −0.0386 (14) | −0.0308 (14) | 0.0361 (14) |
C16 | 0.0543 (13) | 0.0409 (11) | 0.0670 (13) | −0.0190 (10) | −0.0199 (11) | 0.0028 (10) |
C17 | 0.0742 (17) | 0.0421 (12) | 0.0733 (14) | 0.0039 (11) | −0.0293 (12) | −0.0160 (11) |
C18 | 0.105 (2) | 0.0466 (14) | 0.108 (2) | 0.0161 (14) | −0.0562 (18) | −0.0294 (15) |
C19 | 0.125 (3) | 0.0394 (14) | 0.124 (3) | −0.0210 (16) | −0.082 (2) | 0.0112 (15) |
C20 | 0.114 (3) | 0.080 (2) | 0.127 (3) | −0.056 (2) | −0.061 (2) | 0.0490 (19) |
C21 | 0.0492 (12) | 0.0522 (12) | 0.0403 (10) | −0.0096 (9) | −0.0050 (9) | 0.0028 (9) |
S1 | 0.0692 (4) | 0.0499 (3) | 0.0790 (4) | −0.0112 (3) | −0.0234 (3) | −0.0076 (3) |
N3 | 0.0526 (11) | 0.0499 (10) | 0.0607 (10) | −0.0181 (8) | −0.0158 (8) | 0.0122 (8) |
C22 | 0.0467 (12) | 0.0584 (13) | 0.0360 (10) | −0.0129 (9) | −0.0055 (8) | 0.0083 (9) |
C23 | 0.0503 (12) | 0.0588 (13) | 0.0358 (10) | −0.0164 (10) | −0.0002 (8) | 0.0081 (9) |
C24 | 0.0514 (13) | 0.0651 (13) | 0.0459 (11) | −0.0063 (10) | 0.0028 (9) | 0.0078 (10) |
C25 | 0.0412 (12) | 0.0847 (17) | 0.0532 (12) | −0.0121 (11) | 0.0010 (9) | 0.0001 (11) |
C26 | 0.0512 (13) | 0.0697 (15) | 0.0507 (12) | −0.0208 (11) | −0.0028 (10) | −0.0012 (11) |
C27 | 0.0540 (13) | 0.0604 (13) | 0.0466 (11) | −0.0157 (10) | −0.0042 (9) | 0.0019 (10) |
O3 | 0.0631 (10) | 0.0515 (9) | 0.0618 (9) | −0.0154 (7) | −0.0130 (7) | 0.0138 (7) |
C28 | 0.0714 (16) | 0.0558 (14) | 0.0570 (13) | −0.0106 (11) | 0.0066 (11) | 0.0007 (10) |
N1—C21 | 1.365 (2) | C13—C14 | 1.343 (4) |
N1—N2 | 1.399 (2) | C13—H13 | 0.9500 |
N1—N2 | 1.399 (2) | C14—C15 | 1.400 (4) |
N1—C3 | 1.464 (2) | C14—H14 | 0.9500 |
N2—C1 | 1.295 (2) | C15—C20 | 1.414 (4) |
C1—N2 | 1.295 (2) | C15—C16 | 1.430 (3) |
C1—C4 | 1.448 (2) | C16—C17 | 1.410 (3) |
C1—C2 | 1.499 (2) | C17—C18 | 1.377 (3) |
C2—C3 | 1.536 (2) | C17—H17 | 0.9500 |
C2—H2A | 0.9900 | C18—C19 | 1.408 (5) |
C2—H2B | 0.9900 | C18—H18 | 0.9500 |
C3—C11 | 1.515 (3) | C19—C20 | 1.332 (5) |
C3—H3 | 1.0000 | C19—H19 | 0.9500 |
C4—C9 | 1.400 (2) | C20—H20 | 0.9500 |
C4—C5 | 1.409 (2) | C21—N3 | 1.349 (2) |
C5—O1 | 1.359 (2) | C21—S1 | 1.657 (2) |
C5—C6 | 1.385 (2) | N3—C22 | 1.403 (2) |
O1—H1 | 0.8400 | N3—H3A | 0.8800 |
C6—C7 | 1.380 (3) | C22—C27 | 1.391 (3) |
C6—H6 | 0.9500 | C22—C23 | 1.403 (3) |
C7—O2 | 1.366 (2) | C23—C24 | 1.372 (3) |
C7—C8 | 1.389 (3) | C23—O3 | 1.374 (2) |
C8—C9 | 1.372 (2) | C24—C25 | 1.396 (3) |
C8—H8 | 0.9500 | C24—H24 | 0.9500 |
C9—H9 | 0.9500 | C25—C26 | 1.361 (3) |
O2—C10 | 1.424 (2) | C25—H25 | 0.9500 |
C10—H10A | 0.9800 | C26—C27 | 1.379 (3) |
C10—H10B | 0.9800 | C26—H26 | 0.9500 |
C10—H10C | 0.9800 | C27—H27 | 0.9500 |
C11—C12 | 1.360 (3) | O3—C28 | 1.421 (2) |
C11—C16 | 1.425 (3) | C28—H28A | 0.9800 |
C12—C13 | 1.395 (3) | C28—H28B | 0.9800 |
C12—H12 | 0.9500 | C28—H28C | 0.9800 |
C21—N1—N2 | 121.46 (15) | C14—C13—C12 | 120.0 (3) |
C21—N1—N2 | 121.46 (15) | C14—C13—H13 | 120.0 |
C21—N1—C3 | 126.33 (15) | C12—C13—H13 | 120.0 |
N2—N1—C3 | 112.20 (13) | C13—C14—C15 | 121.8 (3) |
N2—N1—C3 | 112.20 (13) | C13—C14—H14 | 119.1 |
C1—N2—N1 | 108.27 (14) | C15—C14—H14 | 119.1 |
N2—C1—C4 | 121.93 (16) | C14—C15—C20 | 123.5 (3) |
N2—C1—C4 | 121.93 (16) | C14—C15—C16 | 118.7 (2) |
N2—C1—C2 | 113.09 (15) | C20—C15—C16 | 117.8 (3) |
N2—C1—C2 | 113.09 (15) | C17—C16—C11 | 123.1 (2) |
C4—C1—C2 | 124.98 (15) | C17—C16—C15 | 118.7 (2) |
C1—C2—C3 | 102.81 (14) | C11—C16—C15 | 118.1 (2) |
C1—C2—H2A | 111.2 | C18—C17—C16 | 120.7 (3) |
C3—C2—H2A | 111.2 | C18—C17—H17 | 119.7 |
C1—C2—H2B | 111.2 | C16—C17—H17 | 119.7 |
C3—C2—H2B | 111.2 | C17—C18—C19 | 119.9 (3) |
H2A—C2—H2B | 109.1 | C17—C18—H18 | 120.0 |
N1—C3—C11 | 111.62 (16) | C19—C18—H18 | 120.0 |
N1—C3—C2 | 101.35 (14) | C20—C19—C18 | 120.4 (3) |
C11—C3—C2 | 112.06 (14) | C20—C19—H19 | 119.8 |
N1—C3—H3 | 110.5 | C18—C19—H19 | 119.8 |
C11—C3—H3 | 110.5 | C19—C20—C15 | 122.4 (3) |
C2—C3—H3 | 110.5 | C19—C20—H20 | 118.8 |
C9—C4—C5 | 116.99 (16) | C15—C20—H20 | 118.8 |
C9—C4—C1 | 119.93 (16) | N3—C21—N1 | 112.16 (16) |
C5—C4—C1 | 123.08 (16) | N3—C21—S1 | 126.88 (14) |
O1—C5—C6 | 116.67 (17) | N1—C21—S1 | 120.95 (15) |
O1—C5—C4 | 122.55 (16) | C21—N3—C22 | 132.25 (16) |
C6—C5—C4 | 120.77 (17) | C21—N3—H3A | 113.9 |
C5—O1—H1 | 109.5 | C22—N3—H3A | 113.9 |
C7—C6—C5 | 120.16 (18) | C27—C22—N3 | 127.24 (19) |
C7—C6—H6 | 119.9 | C27—C22—C23 | 119.08 (18) |
C5—C6—H6 | 119.9 | N3—C22—C23 | 113.67 (16) |
O2—C7—C6 | 115.31 (17) | C24—C23—O3 | 125.16 (19) |
O2—C7—C8 | 124.18 (17) | C24—C23—C22 | 120.62 (18) |
C6—C7—C8 | 120.49 (17) | O3—C23—C22 | 114.21 (17) |
C9—C8—C7 | 118.95 (18) | C23—C24—C25 | 119.3 (2) |
C9—C8—H8 | 120.5 | C23—C24—H24 | 120.4 |
C7—C8—H8 | 120.5 | C25—C24—H24 | 120.4 |
C8—C9—C4 | 122.63 (18) | C26—C25—C24 | 120.3 (2) |
C8—C9—H9 | 118.7 | C26—C25—H25 | 119.8 |
C4—C9—H9 | 118.7 | C24—C25—H25 | 119.8 |
C7—O2—C10 | 117.75 (16) | C25—C26—C27 | 121.11 (19) |
O2—C10—H10A | 109.5 | C25—C26—H26 | 119.4 |
O2—C10—H10B | 109.5 | C27—C26—H26 | 119.4 |
H10A—C10—H10B | 109.5 | C26—C27—C22 | 119.6 (2) |
O2—C10—H10C | 109.5 | C26—C27—H27 | 120.2 |
H10A—C10—H10C | 109.5 | C22—C27—H27 | 120.2 |
H10B—C10—H10C | 109.5 | C23—O3—C28 | 118.02 (16) |
C12—C11—C16 | 120.0 (2) | O3—C28—H28A | 109.5 |
C12—C11—C3 | 121.35 (18) | O3—C28—H28B | 109.5 |
C16—C11—C3 | 118.59 (19) | H28A—C28—H28B | 109.5 |
C11—C12—C13 | 121.3 (2) | O3—C28—H28C | 109.5 |
C11—C12—H12 | 119.3 | H28A—C28—H28C | 109.5 |
C13—C12—H12 | 119.3 | H28B—C28—H28C | 109.5 |
C21—N1—N2—N2 | 0.00 (19) | C2—C3—C11—C16 | −75.0 (2) |
C3—N1—N2—N2 | 0.0 (2) | C16—C11—C12—C13 | 0.2 (3) |
C21—N1—N2—C1 | −170.99 (17) | C3—C11—C12—C13 | −176.4 (2) |
N2—N1—N2—C1 | 0 (100) | C11—C12—C13—C14 | −1.5 (4) |
C3—N1—N2—C1 | 9.8 (2) | C12—C13—C14—C15 | 1.1 (5) |
N1—N2—C1—N2 | 0 (100) | C13—C14—C15—C20 | −180.0 (3) |
N2—N2—C1—C4 | 0.0 (9) | C13—C14—C15—C16 | 0.4 (4) |
N1—N2—C1—C4 | 179.45 (15) | C12—C11—C16—C17 | −177.63 (18) |
N2—N2—C1—C2 | 0.0 (8) | C3—C11—C16—C17 | −0.9 (3) |
N1—N2—C1—C2 | 0.3 (2) | C12—C11—C16—C15 | 1.3 (3) |
N2—C1—C2—C3 | −9.4 (2) | C3—C11—C16—C15 | 177.99 (17) |
N2—C1—C2—C3 | −9.4 (2) | C14—C15—C16—C17 | 177.4 (2) |
C4—C1—C2—C3 | 171.51 (16) | C20—C15—C16—C17 | −2.3 (3) |
C21—N1—C3—C11 | −74.5 (2) | C14—C15—C16—C11 | −1.6 (3) |
N2—N1—C3—C11 | 104.57 (16) | C20—C15—C16—C11 | 178.78 (19) |
N2—N1—C3—C11 | 104.57 (16) | C11—C16—C17—C18 | −179.67 (18) |
C21—N1—C3—C2 | 166.01 (18) | C15—C16—C17—C18 | 1.4 (3) |
N2—N1—C3—C2 | −14.88 (18) | C16—C17—C18—C19 | −0.6 (3) |
N2—N1—C3—C2 | −14.88 (18) | C17—C18—C19—C20 | 0.8 (4) |
C1—C2—C3—N1 | 13.60 (17) | C18—C19—C20—C15 | −1.7 (4) |
C1—C2—C3—C11 | −105.54 (17) | C14—C15—C20—C19 | −177.1 (3) |
N2—C1—C4—C9 | −175.47 (17) | C16—C15—C20—C19 | 2.5 (4) |
N2—C1—C4—C9 | −175.47 (17) | N2—N1—C21—N3 | 1.1 (3) |
C2—C1—C4—C9 | 3.6 (3) | N2—N1—C21—N3 | 1.1 (3) |
N2—C1—C4—C5 | 3.4 (3) | C3—N1—C21—N3 | −179.84 (17) |
N2—C1—C4—C5 | 3.4 (3) | N2—N1—C21—S1 | −178.43 (13) |
C2—C1—C4—C5 | −177.52 (17) | N2—N1—C21—S1 | −178.43 (13) |
C9—C4—C5—O1 | 179.67 (17) | C3—N1—C21—S1 | 0.6 (3) |
C1—C4—C5—O1 | 0.7 (3) | N1—C21—N3—C22 | −167.46 (19) |
C9—C4—C5—C6 | 0.2 (3) | S1—C21—N3—C22 | 12.1 (3) |
C1—C4—C5—C6 | −178.75 (17) | C21—N3—C22—C27 | −9.8 (4) |
O1—C5—C6—C7 | −178.71 (18) | C21—N3—C22—C23 | 168.6 (2) |
C4—C5—C6—C7 | 0.8 (3) | C27—C22—C23—C24 | 0.6 (3) |
C5—C6—C7—O2 | 177.29 (16) | N3—C22—C23—C24 | −177.93 (17) |
C5—C6—C7—C8 | −1.4 (3) | C27—C22—C23—O3 | −179.93 (17) |
O2—C7—C8—C9 | −177.58 (17) | N3—C22—C23—O3 | 1.6 (2) |
C6—C7—C8—C9 | 1.0 (3) | O3—C23—C24—C25 | −179.18 (18) |
C7—C8—C9—C4 | 0.0 (3) | C22—C23—C24—C25 | 0.3 (3) |
C5—C4—C9—C8 | −0.6 (3) | C23—C24—C25—C26 | −0.3 (3) |
C1—C4—C9—C8 | 178.38 (17) | C24—C25—C26—C27 | −0.5 (3) |
C6—C7—O2—C10 | −178.99 (17) | C25—C26—C27—C22 | 1.3 (3) |
C8—C7—O2—C10 | −0.3 (3) | N3—C22—C27—C26 | 176.93 (18) |
N1—C3—C11—C12 | −11.2 (2) | C23—C22—C27—C26 | −1.4 (3) |
C2—C3—C11—C12 | 101.7 (2) | C24—C23—O3—C28 | 5.4 (3) |
N1—C3—C11—C16 | 172.14 (15) | C22—C23—O3—C28 | −174.03 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.84 | 1.96 | 2.6889 (19) | 145 |
C18—H18···S1i | 0.95 | 2.96 | 3.712 (2) | 137 |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Funding information
Funding for this research was provided by: the Basic Science Research Program (award No. NRF-2016R1D1A1B03931623).
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