organic compounds
2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-[4-(methylsulfanyl)phenyl]hydrazine-1-carbothioamide
aİlke Education and Health Foundation, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Yüzüncü Yıl University, 65080 Tuşba, Van, Turkey, cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ístanbul University, 34116 Beyazıt–Ístanbul, Turkey, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and eDepartment of Physics, Faculty of Arts and Sciences, Sinop University, 57010 Sinop, Turkey
*Correspondence e-mail: zeliha.atioglu@kapadokya.edu.tr
The title molecule, C17H15FN4OS2, obtained from 5-fluoro-1-methyl-1H-indol-2,3-dione, and 3-[4-(methylsulfanyl)phenyl]thiosemicarbazide, has an essentially planar conformation (r.m.s deviation for all non-H atoms = 0.116 Å). Intramolecular N—H⋯N and N—H⋯O hydrogen bonds generate S(5) and S(6) ring motifs, respectively. In the crystal, C—H⋯S hydrogen bonds occur between layers of molecules parallel to the (10-1) plane. Face-to-face π–π stacking interactions are also observed.
Keywords: crystal structure; intramolecular hydrogen bonds; π–π stacking interactions; synthesis; 5-fluoro-1H-indole-2,3-dione.
CCDC reference: 1547812
Structure description
The indole ring system is an important structural component in many pharmaceutical agents, including compounds with antiviral, anti-inflammatory and antitumor properties (Ma et al., 2015). 1H-Indole-2,3-dione (isatin) has a wide spectrum of biological properties, such as cytotoxic and antineoplastic effects. Isatin derivatives with halogens and N-alkylhaloisatins have been reported to exhibit anticancer activity (Podichetty et al., 2009). The biological activities of thiosemicarbazones, such as anticancer, antiviral, antimicrobial etc, have been known for a long time. Isatin 3-thiosemicarbazone derivatives, which have anti-HIV effects, are used as prophylaxes against smallpox and vaccinia viruses (Bal et al., 2005; Hall et al., 2009). Isatin 3-[N4-(phenyl substituted) thiosemicarbazone] derivatives have been shown to be have significantly more multidrug resistant-selective activity than N4-alkyl and N4-cycloalkyl thiosemicarbazone derivatives (Hall et al., 2009, 2011).
In the title compound (Fig. 1), the N—N—C=S and N—N—C(=S)—N torsion angles are 170.0 (3) and −9.6 (6)°, respectively. Intramolecular N—H⋯N and N—H⋯O hydrogen bonds (Table 1) generate S(5) and S(6) ring motifs, respectively (Fig. 2). All bond lengths and angles are within normal ranges and agree with those reported for (3E)-3-[(4-butylphenyl)imino]-1,3-dihydro-2H-indol-2-one (Akkurt et al., 2003), N′-[(2Z)-3-allyl-4-oxo-1,3-thiazolidin-2-ylidene]-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (Akkurt et al., 2009), 2-(4-isobutylphenyl)-N′-[(3Z)-2-oxoindolin-3-ylidene]propanohydrazide (Mohamed et al., 2012), 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazone derivatives (Özbey et al., 2006; Karayel et al., 2015) and 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives (Kaynak et al., 2013).
In the crystal, C—H⋯S hydrogen bonds (Table 1) occur between layers of molecules located parallel to the (10) plane (Fig. 3). Face-to-face π–π stacking interactions [Cg1⋯Cg3(x, 1 − y, − + z) = 3.615 (3) Å and Cg2⋯Cg3(−1 + x, 1 − y, − + z) = 3.835 (3) Å, where Cg1, Cg2 and Cg3 are the centroids of the N1/C1/C6–C8, C1–C6 and C11–C16 rings, respectively] are also observed.
Synthesis and crystallization
Steps in the synthesis of the title compound (5) are shown in Fig. 4.
3-[4-(Methylsulfanyl)phenyl]thiosemicarbazide (2)
To a solution of hydrazine hydrate (5 mmol) in ethanol (10 ml), a suspension of 4-(methylsulfanyl)phenylisothiocyanate (1) (5 mmol) in ethanol (10 ml) was added dropwise with vigorous stirring and cooling in an ice bath. The mixture was allowed to stand overnight. The crystals formed were recrystallized from ethanol solution.
5-Fluoro-1-methyl-1H-indole-2,3-dione (4)
A suspension of 5-fluoro-1H-indole-2,3-dione (3) (5 mmol), K2CO3 (7 mmol) and KI (1 mmol) in anhydrous DMF (5 ml) was stirred for 30 min at room temperature. After addition of iodomethane (15 mmol), the mixture was refluxed for 4 h. The product was poured onto ice–water then filtered.
5-Fluoro-1-methyl-1H-indole-2,3-dione 3-[4-(methylsulfanyl)phenyl] thiosemicarbazone (5)
A solution of N-[(4-methylsulfanyl)phenyl]thiosemicarbazide (2) (2.5 mmol) in ethanol (10 ml) was added to a solution of 5-fluoro-1-methyl-1H-indole-2,3-dione (4) (2.5 mmol) in ethanol (20 ml). The mixture was refluxed on a water bath for 10 h. The product formed after cooling was filtered and washed with ethanol or recrystallized from ethanol. Orange crystals were obtained in 94% yield, m.p. 508–511 K.
IR (KBr): ν 3269, 3226 (NH), 1681 (C=O), 1274 (C=S); 1H NMR (DMSO-d6; 400 MHz): δ 2.49 (s, 3H, SCH3), 3.21 (s, 3H, ind. N—CH3), 7.15 (dd, J = 8.60, 4.00 Hz, 1H, ind. C7—H), 7.26–7.32 (m, 1H, ind. C6—H), 7.30 (d, J = 8.60 Hz, 2H, fen. C3,5-H), 7.55 (d, J = 8.60 Hz, 2H, fen. C2,6-H), 7.64 (dd, J = 8.00, 2.66 Hz, 1H, ind. C4—H), 10.81 (s, 1H, N4—H), 12.56 (s, 1H, N2—H). Analysis calculated for C17H15FN4OS2 (374.45): C, 54.53; H, 4.04; N, 14.96. Found: C, 54.24; H, 4.09; N, 14.99. 3.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1547812
https://doi.org/10.1107/S241431461700671X/bt4047sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700671X/bt4047Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461700671X/bt4047Isup3.cml
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C17H15FN4OS2 | F(000) = 776 |
Mr = 374.45 | Dx = 1.434 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 9917 reflections |
a = 7.9661 (6) Å | θ = 3.2–26.4° |
b = 20.8680 (17) Å | µ = 0.33 mm−1 |
c = 10.4774 (9) Å | T = 296 K |
β = 95.257 (3)° | Block, orange |
V = 1734.4 (2) Å3 | 0.19 × 0.15 × 0.14 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 2910 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.036 |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | θmax = 26.4°, θmin = 3.2° |
Tmin = 0.663, Tmax = 0.745 | h = −9→8 |
18078 measured reflections | k = −26→26 |
3245 independent reflections | l = −13→13 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0199P)2 + 2.3048P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.044 | (Δ/σ)max < 0.001 |
wR(F2) = 0.096 | Δρmax = 0.18 e Å−3 |
S = 1.10 | Δρmin = −0.23 e Å−3 |
3245 reflections | Extinction correction: SHELXL-2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
236 parameters | Extinction coefficient: 0.016 (2) |
2 restraints | Absolute structure: Flack (1983) |
Hydrogen site location: mixed | Absolute structure parameter: 0.09 (12) |
Experimental. The melting point was estimated with a Buchi 540 melting-point apparatus in an open capillary and is uncorrected. Elemental analysis was performed on a Thermo Finnigan Flash EA 1112 elemental analyzer. IR spectra was recorded on a KBr disc using a Perkin– Elmer Model 1600 FT–IR spectrometer. The 1H NMR spectra were obtained on Bruker Avance DPX 400 spectrophotometer using DMSO-d6. All chemicals and solvents were purchased from Merck–Schuchardt and Aldrich. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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. C-bound H atoms were placed in calculated positions (C—H = 0.93 Å and 0.96 Å) and N-bound H atoms were found from a difference Fourier map. All H atoms were refined using the riding-model approximation with Uiso(H) = 1.2 or 1.5 Ueq(C,N). The coordinates of the H atoms bonded to N were refined. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.7480 (2) | 0.42568 (6) | 0.83501 (13) | 0.0655 (5) | |
S2 | 0.8897 (2) | 0.76426 (7) | 0.92299 (15) | 0.0745 (6) | |
F1 | 0.1155 (5) | 0.53841 (19) | 0.0901 (3) | 0.0908 (16) | |
O1 | 0.4820 (5) | 0.30064 (15) | 0.5192 (3) | 0.0583 (13) | |
N1 | 0.3211 (5) | 0.31394 (17) | 0.3247 (3) | 0.0492 (14) | |
N2 | 0.4943 (5) | 0.44513 (16) | 0.5056 (3) | 0.0428 (11) | |
N3 | 0.5831 (5) | 0.41981 (18) | 0.6103 (3) | 0.0459 (11) | |
N4 | 0.6774 (5) | 0.52015 (16) | 0.6595 (3) | 0.0428 (10) | |
C1 | 0.2595 (6) | 0.3667 (2) | 0.2503 (4) | 0.0452 (16) | |
C2 | 0.1575 (6) | 0.3670 (3) | 0.1361 (4) | 0.0603 (18) | |
C3 | 0.1126 (6) | 0.4254 (3) | 0.0825 (4) | 0.0639 (18) | |
C4 | 0.1651 (6) | 0.4813 (3) | 0.1437 (4) | 0.0591 (19) | |
C5 | 0.2671 (6) | 0.4819 (2) | 0.2571 (4) | 0.0503 (17) | |
C6 | 0.3147 (5) | 0.4240 (2) | 0.3100 (4) | 0.0426 (12) | |
C7 | 0.4150 (5) | 0.40606 (19) | 0.4266 (4) | 0.0407 (11) | |
C8 | 0.4131 (6) | 0.33431 (19) | 0.4325 (4) | 0.0450 (14) | |
C9 | 0.2977 (8) | 0.2468 (2) | 0.2914 (6) | 0.072 (2) | |
C10 | 0.6701 (6) | 0.45967 (19) | 0.6982 (4) | 0.0432 (14) | |
C11 | 0.7340 (5) | 0.57666 (19) | 0.7249 (3) | 0.0379 (11) | |
C12 | 0.8323 (6) | 0.5784 (2) | 0.8413 (4) | 0.0467 (14) | |
C13 | 0.8783 (6) | 0.6365 (2) | 0.8973 (4) | 0.0502 (16) | |
C14 | 0.8271 (6) | 0.6943 (2) | 0.8390 (4) | 0.0497 (16) | |
C15 | 0.7321 (6) | 0.6925 (2) | 0.7212 (4) | 0.0498 (14) | |
C16 | 0.6853 (6) | 0.63372 (19) | 0.6650 (4) | 0.0448 (14) | |
C17 | 0.8004 (10) | 0.8275 (3) | 0.8227 (7) | 0.090 (3) | |
H2 | 0.12060 | 0.32900 | 0.09680 | 0.0720* | |
H3 | 0.04650 | 0.42720 | 0.00470 | 0.0760* | |
H3N | 0.578 (7) | 0.379 (2) | 0.626 (5) | 0.0550* | |
H4N | 0.621 (6) | 0.529 (2) | 0.583 (5) | 0.0520* | |
H5 | 0.30230 | 0.52030 | 0.29620 | 0.0600* | |
H9A | 0.34370 | 0.23840 | 0.21150 | 0.1080* | |
H9B | 0.17950 | 0.23680 | 0.28330 | 0.1080* | |
H9C | 0.35430 | 0.22070 | 0.35740 | 0.1080* | |
H12 | 0.86720 | 0.54040 | 0.88170 | 0.0560* | |
H13 | 0.94450 | 0.63710 | 0.97510 | 0.0600* | |
H15 | 0.69950 | 0.73050 | 0.67970 | 0.0600* | |
H16 | 0.62070 | 0.63290 | 0.58650 | 0.0540* | |
H17A | 0.84050 | 0.82420 | 0.73930 | 0.1350* | |
H17B | 0.83330 | 0.86820 | 0.86000 | 0.1350* | |
H17C | 0.67980 | 0.82410 | 0.81520 | 0.1350* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0947 (11) | 0.0465 (6) | 0.0489 (6) | −0.0041 (7) | −0.0286 (6) | 0.0070 (6) |
S2 | 0.0981 (12) | 0.0552 (8) | 0.0695 (9) | −0.0178 (8) | 0.0044 (8) | −0.0215 (7) |
F1 | 0.086 (3) | 0.104 (3) | 0.078 (2) | 0.023 (2) | −0.0169 (19) | 0.031 (2) |
O1 | 0.076 (3) | 0.0428 (17) | 0.055 (2) | −0.0027 (16) | −0.0003 (17) | 0.0041 (14) |
N1 | 0.052 (3) | 0.047 (2) | 0.048 (2) | −0.0094 (17) | 0.0018 (18) | −0.0098 (16) |
N2 | 0.047 (2) | 0.0440 (19) | 0.0349 (17) | −0.0005 (16) | −0.0093 (15) | −0.0005 (14) |
N3 | 0.058 (2) | 0.0360 (18) | 0.0401 (19) | −0.0043 (16) | −0.0151 (16) | 0.0027 (15) |
N4 | 0.055 (2) | 0.0383 (18) | 0.0321 (16) | −0.0053 (16) | −0.0123 (15) | 0.0016 (13) |
C1 | 0.040 (3) | 0.058 (3) | 0.038 (2) | −0.0052 (19) | 0.0055 (19) | −0.0100 (18) |
C2 | 0.043 (3) | 0.094 (4) | 0.042 (2) | −0.006 (3) | −0.006 (2) | −0.021 (3) |
C3 | 0.044 (3) | 0.104 (4) | 0.041 (2) | 0.002 (3) | −0.011 (2) | −0.008 (3) |
C4 | 0.046 (3) | 0.083 (4) | 0.047 (3) | 0.012 (2) | −0.003 (2) | 0.018 (2) |
C5 | 0.047 (3) | 0.054 (3) | 0.048 (3) | −0.003 (2) | −0.006 (2) | 0.0053 (19) |
C6 | 0.037 (2) | 0.054 (2) | 0.035 (2) | −0.0059 (19) | −0.0065 (17) | −0.0047 (17) |
C7 | 0.043 (2) | 0.042 (2) | 0.0356 (19) | −0.0073 (18) | −0.0044 (17) | −0.0022 (17) |
C8 | 0.050 (3) | 0.040 (2) | 0.045 (2) | −0.0059 (19) | 0.0037 (19) | −0.0038 (19) |
C9 | 0.082 (4) | 0.052 (3) | 0.083 (4) | −0.014 (3) | 0.009 (3) | −0.028 (3) |
C10 | 0.051 (3) | 0.038 (2) | 0.039 (2) | −0.0008 (19) | −0.0039 (18) | −0.0011 (17) |
C11 | 0.038 (2) | 0.043 (2) | 0.0323 (19) | −0.0045 (17) | 0.0010 (16) | −0.0023 (16) |
C12 | 0.051 (3) | 0.043 (2) | 0.044 (2) | −0.0045 (19) | −0.007 (2) | 0.0008 (18) |
C13 | 0.057 (3) | 0.056 (3) | 0.036 (2) | −0.010 (2) | −0.005 (2) | −0.0051 (19) |
C14 | 0.055 (3) | 0.050 (3) | 0.045 (2) | −0.011 (2) | 0.010 (2) | −0.0097 (19) |
C15 | 0.059 (3) | 0.041 (2) | 0.049 (2) | 0.0017 (19) | 0.003 (2) | 0.0015 (18) |
C16 | 0.055 (3) | 0.039 (2) | 0.039 (2) | 0.0029 (19) | −0.0030 (19) | −0.0009 (16) |
C17 | 0.137 (7) | 0.044 (3) | 0.092 (4) | −0.012 (3) | 0.022 (4) | −0.013 (3) |
S1—C10 | 1.667 (4) | C6—C7 | 1.446 (6) |
S2—C14 | 1.753 (4) | C7—C8 | 1.499 (6) |
S2—C17 | 1.793 (7) | C11—C16 | 1.385 (6) |
F1—C4 | 1.361 (7) | C11—C12 | 1.388 (5) |
O1—C8 | 1.236 (5) | C12—C13 | 1.382 (6) |
N1—C1 | 1.411 (5) | C13—C14 | 1.396 (6) |
N1—C8 | 1.357 (5) | C14—C15 | 1.388 (6) |
N1—C9 | 1.452 (6) | C15—C16 | 1.397 (6) |
N2—N3 | 1.357 (5) | C2—H2 | 0.9300 |
N2—C7 | 1.286 (5) | C3—H3 | 0.9300 |
N3—C10 | 1.380 (6) | C5—H5 | 0.9300 |
N4—C10 | 1.329 (5) | C9—H9A | 0.9600 |
N4—C11 | 1.417 (5) | C9—H9B | 0.9600 |
C1—C2 | 1.383 (6) | C9—H9C | 0.9600 |
C1—C6 | 1.401 (6) | C12—H12 | 0.9300 |
C2—C3 | 1.375 (8) | C13—H13 | 0.9300 |
C3—C4 | 1.378 (8) | C15—H15 | 0.9300 |
N3—H3N | 0.87 (4) | C16—H16 | 0.9300 |
N4—H4N | 0.90 (5) | C17—H17A | 0.9600 |
C4—C5 | 1.377 (6) | C17—H17B | 0.9600 |
C5—C6 | 1.368 (6) | C17—H17C | 0.9600 |
C14—S2—C17 | 103.9 (3) | N4—C11—C12 | 125.2 (4) |
C1—N1—C8 | 110.5 (3) | C11—C12—C13 | 120.2 (4) |
C1—N1—C9 | 126.2 (4) | C12—C13—C14 | 121.1 (4) |
C8—N1—C9 | 123.4 (4) | S2—C14—C13 | 116.2 (3) |
N3—N2—C7 | 117.6 (3) | C13—C14—C15 | 118.7 (4) |
N2—N3—C10 | 119.9 (4) | S2—C14—C15 | 125.2 (3) |
C10—N4—C11 | 131.6 (3) | C14—C15—C16 | 120.1 (4) |
N1—C1—C2 | 128.9 (4) | C11—C16—C15 | 120.8 (4) |
N1—C1—C6 | 109.9 (4) | C1—C2—H2 | 121.00 |
C2—C1—C6 | 121.2 (4) | C3—C2—H2 | 121.00 |
C1—C2—C3 | 117.9 (5) | C2—C3—H3 | 120.00 |
C2—C3—C4 | 120.3 (4) | C4—C3—H3 | 120.00 |
N2—N3—H3N | 120 (3) | C4—C5—H5 | 121.00 |
C10—N3—H3N | 120 (4) | C6—C5—H5 | 121.00 |
F1—C4—C3 | 119.0 (4) | N1—C9—H9A | 110.00 |
C10—N4—H4N | 116 (3) | N1—C9—H9B | 110.00 |
F1—C4—C5 | 118.3 (5) | N1—C9—H9C | 109.00 |
C3—C4—C5 | 122.7 (5) | H9A—C9—H9B | 109.00 |
C11—N4—H4N | 112 (3) | H9A—C9—H9C | 109.00 |
C4—C5—C6 | 117.5 (4) | H9B—C9—H9C | 109.00 |
C1—C6—C5 | 120.6 (4) | C11—C12—H12 | 120.00 |
C1—C6—C7 | 106.4 (4) | C13—C12—H12 | 120.00 |
C5—C6—C7 | 133.0 (4) | C12—C13—H13 | 119.00 |
N2—C7—C8 | 127.8 (4) | C14—C13—H13 | 119.00 |
C6—C7—C8 | 106.7 (3) | C14—C15—H15 | 120.00 |
N2—C7—C6 | 125.5 (4) | C16—C15—H15 | 120.00 |
O1—C8—N1 | 127.1 (4) | C11—C16—H16 | 120.00 |
O1—C8—C7 | 126.3 (4) | C15—C16—H16 | 120.00 |
N1—C8—C7 | 106.6 (3) | S2—C17—H17A | 109.00 |
N3—C10—N4 | 113.7 (4) | S2—C17—H17B | 109.00 |
S1—C10—N3 | 116.2 (3) | S2—C17—H17C | 110.00 |
S1—C10—N4 | 130.0 (3) | H17A—C17—H17B | 109.00 |
N4—C11—C16 | 115.7 (3) | H17A—C17—H17C | 110.00 |
C12—C11—C16 | 119.2 (4) | H17B—C17—H17C | 109.00 |
C17—S2—C14—C15 | 0.8 (5) | C1—C2—C3—C4 | −1.7 (7) |
C17—S2—C14—C13 | −179.1 (4) | C2—C3—C4—F1 | −178.4 (4) |
C9—N1—C1—C2 | 4.2 (8) | C2—C3—C4—C5 | 2.0 (7) |
C8—N1—C1—C6 | 0.9 (5) | C3—C4—C5—C6 | −0.9 (7) |
C8—N1—C1—C2 | −178.1 (5) | F1—C4—C5—C6 | 179.6 (4) |
C9—N1—C8—C7 | 176.4 (4) | C4—C5—C6—C1 | −0.5 (7) |
C1—N1—C8—O1 | 178.5 (5) | C4—C5—C6—C7 | −178.3 (4) |
C9—N1—C1—C6 | −176.8 (5) | C1—C6—C7—C8 | −0.8 (5) |
C1—N1—C8—C7 | −1.4 (5) | C1—C6—C7—N2 | 176.8 (4) |
C9—N1—C8—O1 | −3.7 (8) | C5—C6—C7—C8 | 177.2 (5) |
N3—N2—C7—C6 | −179.8 (4) | C5—C6—C7—N2 | −5.1 (8) |
C7—N2—N3—C10 | −179.8 (4) | C6—C7—C8—O1 | −178.5 (5) |
N3—N2—C7—C8 | −2.6 (7) | C6—C7—C8—N1 | 1.3 (5) |
N2—N3—C10—N4 | −9.6 (6) | N2—C7—C8—O1 | 3.9 (8) |
N2—N3—C10—S1 | 170.0 (3) | N2—C7—C8—N1 | −176.2 (4) |
C10—N4—C11—C12 | 15.7 (7) | N4—C11—C16—C15 | 179.3 (4) |
C11—N4—C10—S1 | −8.7 (8) | C12—C11—C16—C15 | −0.9 (7) |
C11—N4—C10—N3 | 170.8 (4) | N4—C11—C12—C13 | −179.1 (4) |
C10—N4—C11—C16 | −164.5 (5) | C16—C11—C12—C13 | 1.1 (7) |
N1—C1—C2—C3 | 179.2 (4) | C11—C12—C13—C14 | 0.2 (7) |
C2—C1—C6—C7 | 179.1 (4) | C12—C13—C14—C15 | −1.7 (7) |
N1—C1—C6—C7 | 0.0 (5) | C12—C13—C14—S2 | 178.3 (4) |
C6—C1—C2—C3 | 0.4 (7) | S2—C14—C15—C16 | −178.1 (4) |
C2—C1—C6—C5 | 0.8 (7) | C13—C14—C15—C16 | 1.9 (7) |
N1—C1—C6—C5 | −178.3 (4) | C14—C15—C16—C11 | −0.6 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3N···O1 | 0.87 (4) | 2.09 (5) | 2.757 (5) | 133 (5) |
N4—H4N···N2 | 0.90 (5) | 2.14 (5) | 2.598 (5) | 110 (3) |
C3—H3···S1i | 0.93 | 2.84 | 3.712 (5) | 158 |
C9—H9B···S2ii | 0.96 | 2.84 | 3.652 (7) | 142 |
C9—H9C···O1 | 0.96 | 2.52 | 2.911 (7) | 104 |
C12—H12···S1 | 0.93 | 2.61 | 3.256 (4) | 128 |
Symmetry codes: (i) x−1, y, z−1; (ii) x−1, −y+1, z−1/2. |
Acknowledgements
The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.
Funding information
Funding for this research was provided by: TÜBİTAK (award No. 1003–215S011).
References
Akkurt, M., Karaca, S., Cihan, G., Çapan, G. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1009–o1010. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akkurt, M., Öztürk, S., Erçağ, A., Özgür, M. Ü. & Heinemann, F. W. (2003). Acta Cryst. E59, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bal, T. R., Anand, B., Yogeeswari, P. & Sriram, D. (2005). Bioorg. Med. Chem. Lett. 15, 4451–4455. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hall, M. D., Brimacombe, K. R., Varonka, M. S., Pluchino, K. M., Monda, J. K., Li, J., Walsh, M. J., Boxer, M. B., Warren, T. H., Fales, H. M. & Gottesman, M. M. (2011). J. Med. Chem. 54, 5878–5889. Web of Science CSD CrossRef CAS PubMed Google Scholar
Hall, M. D., Salam, N. K., Hellawell, J. L., Fales, H. M., Kensler, C. B., Ludwig, J. A., Szakács, G., Hibbs, D. E. & Gottesman, M. M. (2009). J. Med. Chem. 52, 3191–3204. Web of Science CrossRef PubMed CAS Google Scholar
Karayel, A., Kaynak, F. B., Karalı, N. & Özbey, S. (2015). Acta Cryst. A71, s468. CrossRef IUCr Journals Google Scholar
Kaynak, F. B., Özbey, S. & Karalı, N. (2013). J. Mol. Struct. 1049, 157–164. Web of Science CSD CrossRef CAS Google Scholar
Ma, J., Bao, G., Wang, L., Li, W., Xu, B., Du, B., Lv, J., Zhai, X. & Gong, P. (2015). Eur. J. Med. Chem. 96, 173–186. Web of Science CrossRef CAS PubMed Google Scholar
Mohamed, S. K., Akkurt, M., Albayati, M. R., Singh, K. & Potgieter, H. (2012). Acta Cryst. E68, o1222–o1223. CSD CrossRef IUCr Journals Google Scholar
Özbey, S., Kaynak, F. B., Eriksson, L., Karali, N. & Gürsoy, A. (2006). Acta Cryst. A62, s174. CrossRef IUCr Journals Google Scholar
Podichetty, A. K., Faust, A., Kopka, K., Wagner, S., Schober, O., Schäfers, M. & Haufe, G. (2009). Bioorg. Med. Chem. 17, 2680–2688. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef IUCr Journals Google Scholar
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