(5Z)-3-(2-Oxoprop­yl)-5-(3,4,5-tri­meth­oxy­benzyl­idene)-1,3-thia­zol­idine-2,4-dione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; El-Kashef, H.; Lebegue, N.; Albayati, M.R.

doi:10.1107/S2414314616019593

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 12| December 2016| x161959

https://doi.org/10.1107/S2414314616019593

Open

access

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Hussein El-Kashef,^e Nicolas Lebegue ^f and Mustafa R. Albayati ^g ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt, ^fUniv. Lille, Inserm, CHU Lille, UMR-S 1172–JPArc–Centre de Recherche Jean-Pierre AUBERT Neurosciences et Cancer, F-59000 Lille, France, and ^gKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by P. C. Healy, Griffith University, Australia (Received 7 December 2016; accepted 7 December 2016; online 13 December 2016)

In the crystal of the title molecule, C₁₆H₁₇NO₆S, there are three sets of intermolecular C—H⋯O hydrogen bonds, as well as two sets of intermolecular C—H⋯π(ring) interactions. In addition, the thiazolidene rings participate in offset π–π stacking interactions [centroid–centroid distance = 3.685 (1) Å]. These generate small channels running parallel to the a axis with approximate cross-sections of 3.7 × 8.1 Å.

Keywords: crystal structure; hydrogen bonds; C—H⋯π(ring) interactions; thiazolidinones; azomethene.

CCDC reference: 1521358

Structure description

Thiazolidine-2,4-dione scaffold compounds are considered to be an important class of heterocycles due to their diverse biological activities. They have been reported to exhibit anti-cancer (Ashok & Vanaja, 2016 ; Wei et al., 2009 ; Xia et al., 2009 ), anti-plasmodial inhibitor (Sharma et al., 2015 ), anti-leishmanial (Leite et al., 2016 ), anti-inflammatory (Barros et al., 2010 ), anti-microbial (Liu et al., 2011 ), anti-oxidant and anti-hyperglycemic activities (Koppireddi et al., 2013 ; Oakes et al., 1994 ). In this context, we report herein the synthesis and crystal structure of the title compound.

In the title molecule (Fig. 1), the dihedral angle between the five- and six-membered ring is 17.67 (7)°. In the crystal, there are small channels of approximately 3.7 x 8.1 Å running parallel to the a axis (Fig. 2). In addition to the three sets of C—H⋯O hydrogen bonds (Table 1 and Figs. 2 and 3), there is an offset π–π stacking interaction between the thiazolidene ring and its counterpart at 1 − x, 1 − y, −z [centroid–centroid distance = 3.6854 (7) Å] and two intermolecular C—H⋯π(ring) interactions (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and S1/N1/C11–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O6ⁱ	0.942 (14)	2.398 (14)	3.3108 (14)	163.2 (12)
C7—H7A⋯O5ⁱⁱ	0.971 (15)	2.482 (15)	3.4434 (15)	170.4 (13)
C14—H14A⋯O5ⁱⁱⁱ	1.016 (15)	2.335 (15)	3.2659 (14)	151.8 (11)
C7—H7C⋯Cg1^iv	0.994 (15)	2.755 (15)	3.5131 (14)	133.3 (11)
C9—H9C⋯Cg2ⁱ	1.001 (14)	2.900 (15)	3.8441 (14)	157.5 (11)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z; (iv) -x, -y+1, -z+1.

Figure 1
The title molecule, showing the atom-labeling scheme and 50% probability ellipsoids.

Figure 2
Packing viewed along the a axis with C—H⋯O hydrogen bonds shown as dotted lines.

Figure 3
Detail of the intermolecular interactions: offset π-stacking (purple dotted line); C—H⋯π(ring) (orange dotted lines); C—H⋯O (black dotted lines) [symmetry codes: (i) 1 − x, 1 − y, −z; (ii) −1 + x, y, z; (iii) −x, 1 − y, 1 − z].

Synthesis and crystallization

A mixture of 5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione potassium salt (10 mmol, 3.33 g) and chloroacetone (11 mmol, 1.02 g, 0.91 mL), in DMF (10 mL) was heated under gentle reflux for 8 h. The reaction mixture was cooled to room temperature and the resulting precipitate was filtered off, washed with water and recrystallized from ethanol and a few drops of dioxane to give good quality crystals suitable for X-ray diffraction (m.p. 411–413 K, 86% yield).

¹H NMR (300 MHz, DMSO-d₆): d 2.52 (s, 3H), 3.74 (s, 3H), 3.84 (s, 6H), 4.68 (s, 2H), 6.96 (s, 2H), 7.92 (s, 1H); ¹³C NMR (75 MHz, DMSO-d₆): d 27.5, 50.7, 56.5, 60.6, 108.1, 120.2, 128.7, 134.3, 140.1, 153.7 165.4, 167.2, and 200.8. m/z = 352 [M + H]⁺.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₆S
M_r	351.36
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.2771 (5), 9.9612 (7), 11.9257 (8)
α, β, γ (°)	78.778 (1), 75.616 (1), 72.829 (1)
V (Å³)	793.16 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.33 × 0.22 × 0.21

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.88, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	15337, 4235, 3660
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.111, 1.12
No. of reflections	4235
No. of parameters	285
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.24
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1521358

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616019593/hg4018sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616019593/hg4018Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione top

Crystal data top

C₁₆H₁₇NO₆S	Z = 2
M_r = 351.36	F(000) = 368
Triclinic, P1	D_x = 1.471 Mg m⁻³
a = 7.2771 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9612 (7) Å	Cell parameters from 9211 reflections
c = 11.9257 (8) Å	θ = 2.6–29.3°
α = 78.778 (1)°	µ = 0.24 mm⁻¹
β = 75.616 (1)°	T = 100 K
γ = 72.829 (1)°	Block, colourless
V = 793.16 (9) Å³	0.33 × 0.22 × 0.21 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4235 independent reflections
Radiation source: fine-focus sealed tube	3660 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.3°, θ_min = 1.8°
φ and ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
T_min = 0.88, T_max = 0.95	l = −16→16
15337 measured reflections

Refinement top

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	All H-atom parameters refined
S = 1.12	w = 1/[σ²(F_o²) + (0.0762P)² + 0.0197P] where P = (F_o² + 2F_c²)/3
4235 reflections	(Δ/σ)_max < 0.001
285 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames,

each of width 0.5° in ω, colllected at φ = 0.00,

90.00 and 180.00° and 2 sets of 800 frames, each of

width 0.45° in φ, collected at ω = –30.00 and 210.00°.

The scan time was 15 sec/frame.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.48040 (4)	0.43973 (3)	0.23681 (2)	0.01742 (10)
O1	0.03935 (12)	0.33614 (9)	0.63528 (7)	0.01876 (18)
O2	−0.28654 (12)	0.25762 (9)	0.64722 (7)	0.01887 (18)
O3	−0.33832 (11)	0.15463 (9)	0.46574 (7)	0.01978 (19)
O4	0.52749 (13)	0.21005 (10)	0.00080 (7)	0.0234 (2)
O5	0.80964 (14)	0.50044 (10)	0.11411 (8)	0.0261 (2)
O6	0.97444 (13)	0.12856 (9)	0.08413 (7)	0.02220 (19)
N1	0.68693 (13)	0.35869 (10)	0.03734 (8)	0.0158 (2)
C1	0.12221 (16)	0.26129 (12)	0.33290 (9)	0.0155 (2)
C2	0.15413 (16)	0.30468 (12)	0.42980 (9)	0.0161 (2)
H2	0.270 (2)	0.3321 (17)	0.4249 (14)	0.030 (4)*
C3	0.02037 (16)	0.29904 (11)	0.53540 (9)	0.0149 (2)
C4	−0.14759 (16)	0.25128 (11)	0.54493 (9)	0.0153 (2)
C5	−0.17503 (16)	0.20396 (12)	0.44871 (10)	0.0158 (2)
C6	−0.04092 (16)	0.20892 (12)	0.34351 (10)	0.0159 (2)
H6	−0.058 (2)	0.1776 (14)	0.2782 (13)	0.021 (4)*
C7	0.21364 (18)	0.38004 (13)	0.62923 (10)	0.0199 (2)
H7A	0.203 (2)	0.4033 (16)	0.7063 (13)	0.027 (4)*
H7B	0.328 (2)	0.2998 (15)	0.6124 (13)	0.022 (4)*
H7C	0.218 (2)	0.4641 (15)	0.5688 (13)	0.020 (3)*
C8	−0.2732 (2)	0.12561 (14)	0.72236 (11)	0.0234 (3)
H8A	−0.297 (2)	0.0581 (17)	0.6826 (14)	0.030 (4)*
H8B	−0.382 (2)	0.1412 (16)	0.7911 (14)	0.029 (4)*
H8C	−0.145 (3)	0.0923 (17)	0.7438 (14)	0.034 (4)*
C9	−0.33885 (18)	0.07211 (13)	0.38013 (11)	0.0201 (2)
H9A	−0.228 (2)	−0.0124 (15)	0.3783 (12)	0.022 (4)*
H9B	−0.462 (2)	0.0468 (14)	0.4033 (12)	0.017 (3)*
H9C	−0.333 (2)	0.1296 (15)	0.3011 (13)	0.022 (4)*
C10	0.25748 (16)	0.25979 (12)	0.21977 (10)	0.0166 (2)
H10	0.239 (2)	0.2061 (14)	0.1678 (12)	0.017 (3)*
C11	0.40602 (16)	0.32201 (12)	0.17634 (9)	0.0157 (2)
C12	0.53935 (16)	0.28850 (12)	0.06331 (9)	0.0160 (2)
C13	0.68703 (17)	0.43854 (12)	0.12030 (10)	0.0177 (2)
C14	0.85791 (16)	0.32219 (12)	−0.05548 (10)	0.0166 (2)
H14A	0.922 (2)	0.4040 (16)	−0.0822 (13)	0.024 (4)*
H14B	0.819 (2)	0.3053 (15)	−0.1204 (13)	0.020 (3)*
C15	1.00626 (16)	0.18907 (12)	−0.01512 (9)	0.0162 (2)
C16	1.19038 (18)	0.14177 (14)	−0.10274 (11)	0.0206 (2)
H16A	1.154 (2)	0.1391 (18)	−0.1711 (15)	0.037 (4)*
H16B	1.270 (2)	0.0529 (17)	−0.0750 (14)	0.025 (4)*
H16C	1.254 (3)	0.2144 (19)	−0.1146 (16)	0.045 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01803 (16)	0.02014 (16)	0.01488 (15)	−0.00891 (11)	0.00277 (11)	−0.00591 (11)
O1	0.0189 (4)	0.0252 (4)	0.0137 (4)	−0.0090 (3)	−0.0002 (3)	−0.0052 (3)
O2	0.0161 (4)	0.0196 (4)	0.0167 (4)	−0.0048 (3)	0.0070 (3)	−0.0055 (3)
O3	0.0143 (4)	0.0281 (4)	0.0190 (4)	−0.0113 (3)	0.0031 (3)	−0.0072 (3)
O4	0.0235 (4)	0.0344 (5)	0.0172 (4)	−0.0160 (4)	0.0027 (3)	−0.0105 (3)
O5	0.0280 (5)	0.0328 (5)	0.0228 (4)	−0.0206 (4)	0.0054 (4)	−0.0099 (4)
O6	0.0254 (5)	0.0255 (4)	0.0154 (4)	−0.0080 (4)	−0.0023 (3)	−0.0022 (3)
N1	0.0134 (4)	0.0203 (5)	0.0133 (4)	−0.0073 (4)	0.0027 (3)	−0.0039 (3)
C1	0.0135 (5)	0.0184 (5)	0.0136 (5)	−0.0058 (4)	0.0004 (4)	−0.0014 (4)
C2	0.0136 (5)	0.0196 (5)	0.0154 (5)	−0.0065 (4)	−0.0009 (4)	−0.0024 (4)
C3	0.0148 (5)	0.0150 (5)	0.0139 (5)	−0.0029 (4)	−0.0017 (4)	−0.0028 (4)
C4	0.0133 (5)	0.0151 (5)	0.0143 (5)	−0.0033 (4)	0.0031 (4)	−0.0027 (4)
C5	0.0114 (5)	0.0169 (5)	0.0181 (5)	−0.0052 (4)	−0.0001 (4)	−0.0016 (4)
C6	0.0141 (5)	0.0194 (5)	0.0144 (5)	−0.0061 (4)	−0.0003 (4)	−0.0031 (4)
C7	0.0210 (6)	0.0246 (6)	0.0170 (5)	−0.0091 (5)	−0.0039 (4)	−0.0045 (4)
C8	0.0253 (6)	0.0266 (6)	0.0151 (5)	−0.0088 (5)	0.0036 (5)	−0.0021 (5)
C9	0.0193 (6)	0.0239 (6)	0.0206 (6)	−0.0111 (5)	−0.0029 (4)	−0.0039 (5)
C10	0.0146 (5)	0.0215 (5)	0.0140 (5)	−0.0062 (4)	−0.0009 (4)	−0.0034 (4)
C11	0.0142 (5)	0.0190 (5)	0.0136 (5)	−0.0047 (4)	−0.0010 (4)	−0.0034 (4)
C12	0.0134 (5)	0.0205 (5)	0.0142 (5)	−0.0067 (4)	−0.0009 (4)	−0.0017 (4)
C13	0.0178 (5)	0.0192 (5)	0.0165 (5)	−0.0080 (4)	−0.0001 (4)	−0.0028 (4)
C14	0.0138 (5)	0.0207 (5)	0.0143 (5)	−0.0072 (4)	0.0025 (4)	−0.0029 (4)
C15	0.0167 (5)	0.0197 (5)	0.0158 (5)	−0.0092 (4)	−0.0021 (4)	−0.0051 (4)
C16	0.0162 (5)	0.0231 (6)	0.0217 (6)	−0.0063 (5)	0.0005 (4)	−0.0049 (5)

Geometric parameters (Å, º) top

S1—C11	1.7567 (11)	C5—C6	1.3874 (15)
S1—C13	1.7747 (12)	C6—H6	0.942 (14)
O1—C3	1.3629 (13)	C7—H7A	0.971 (15)
O1—C7	1.4405 (14)	C7—H7B	0.979 (15)
O2—C4	1.3762 (13)	C7—H7C	0.994 (15)
O2—C8	1.4320 (15)	C8—H8A	0.969 (16)
O3—C5	1.3714 (13)	C8—H8B	0.988 (15)
O3—C9	1.4312 (14)	C8—H8C	0.977 (17)
O4—C12	1.2134 (14)	C9—H9A	0.980 (15)
O5—C13	1.2067 (14)	C9—H9B	0.966 (14)
O6—C15	1.2191 (14)	C9—H9C	1.001 (14)
N1—C13	1.3851 (14)	C10—C11	1.3466 (15)
N1—C12	1.3900 (14)	C10—H10	0.948 (14)
N1—C14	1.4529 (14)	C11—C12	1.4845 (15)
C1—C6	1.4009 (14)	C14—C15	1.5231 (16)
C1—C2	1.4012 (15)	C14—H14A	1.016 (15)
C1—C10	1.4590 (15)	C14—H14B	0.947 (14)
C2—C3	1.3901 (15)	C15—C16	1.4941 (16)
C2—H2	0.946 (16)	C16—H16A	0.926 (17)
C3—C4	1.4094 (15)	C16—H16B	0.951 (16)
C4—C5	1.3996 (15)	C16—H16C	0.937 (19)

C11—S1—C13	91.48 (5)	H8A—C8—H8C	111.8 (13)
C3—O1—C7	116.50 (9)	H8B—C8—H8C	112.4 (13)
C4—O2—C8	114.25 (8)	O3—C9—H9A	110.0 (8)
C5—O3—C9	115.87 (9)	O3—C9—H9B	106.0 (8)
C13—N1—C12	116.31 (9)	H9A—C9—H9B	111.2 (12)
C13—N1—C14	120.69 (9)	O3—C9—H9C	110.8 (8)
C12—N1—C14	121.22 (9)	H9A—C9—H9C	110.3 (12)
C6—C1—C2	120.03 (10)	H9B—C9—H9C	108.4 (11)
C6—C1—C10	116.52 (9)	C11—C10—C1	130.61 (10)
C2—C1—C10	123.37 (10)	C11—C10—H10	114.0 (9)
C3—C2—C1	119.64 (10)	C1—C10—H10	115.4 (9)
C3—C2—H2	120.0 (9)	C10—C11—C12	119.86 (10)
C1—C2—H2	120.3 (9)	C10—C11—S1	129.49 (9)
O1—C3—C2	124.35 (10)	C12—C11—S1	110.60 (8)
O1—C3—C4	115.33 (9)	O4—C12—N1	123.07 (10)
C2—C3—C4	120.32 (10)	O4—C12—C11	126.41 (10)
O2—C4—C5	120.89 (10)	N1—C12—C11	110.51 (9)
O2—C4—C3	119.44 (9)	O5—C13—N1	124.82 (11)
C5—C4—C3	119.61 (10)	O5—C13—S1	124.25 (9)
O3—C5—C6	123.72 (10)	N1—C13—S1	110.93 (8)
O3—C5—C4	116.29 (10)	N1—C14—C15	111.00 (9)
C6—C5—C4	119.99 (10)	N1—C14—H14A	110.1 (8)
C5—C6—C1	120.34 (10)	C15—C14—H14A	109.8 (8)
C5—C6—H6	120.6 (9)	N1—C14—H14B	109.6 (9)
C1—C6—H6	119.1 (9)	C15—C14—H14B	108.5 (9)
O1—C7—H7A	105.8 (9)	H14A—C14—H14B	107.8 (12)
O1—C7—H7B	108.4 (9)	O6—C15—C16	123.34 (11)
H7A—C7—H7B	109.4 (12)	O6—C15—C14	120.60 (10)
O1—C7—H7C	109.2 (8)	C16—C15—C14	116.04 (10)
H7A—C7—H7C	111.3 (12)	C15—C16—H16A	107.2 (10)
H7B—C7—H7C	112.5 (12)	C15—C16—H16B	111.7 (10)
O2—C8—H8A	108.7 (9)	H16A—C16—H16B	112.3 (14)
O2—C8—H8B	107.5 (9)	C15—C16—H16C	104.2 (11)
H8A—C8—H8B	106.5 (13)	H16A—C16—H16C	109.2 (15)
O2—C8—H8C	109.8 (10)	H16B—C16—H16C	111.7 (14)

C6—C1—C2—C3	−1.73 (17)	C2—C1—C10—C11	−15.5 (2)
C10—C1—C2—C3	−178.19 (10)	C1—C10—C11—C12	172.00 (11)
C7—O1—C3—C2	−1.74 (15)	C1—C10—C11—S1	−5.3 (2)
C7—O1—C3—C4	177.64 (10)	C13—S1—C11—C10	175.08 (11)
C1—C2—C3—O1	178.73 (10)	C13—S1—C11—C12	−2.42 (8)
C1—C2—C3—C4	−0.62 (17)	C13—N1—C12—O4	−176.61 (11)
C8—O2—C4—C5	82.74 (13)	C14—N1—C12—O4	−11.70 (17)
C8—O2—C4—C3	−100.09 (12)	C13—N1—C12—C11	2.50 (14)
O1—C3—C4—O2	6.01 (15)	C14—N1—C12—C11	167.41 (9)
C2—C3—C4—O2	−174.59 (9)	C10—C11—C12—O4	1.81 (18)
O1—C3—C4—C5	−176.78 (10)	S1—C11—C12—O4	179.59 (10)
C2—C3—C4—C5	2.62 (16)	C10—C11—C12—N1	−177.26 (10)
C9—O3—C5—C6	16.49 (16)	S1—C11—C12—N1	0.52 (12)
C9—O3—C5—C4	−163.65 (10)	C12—N1—C13—O5	176.35 (11)
O2—C4—C5—O3	−4.97 (15)	C14—N1—C13—O5	11.36 (18)
C3—C4—C5—O3	177.86 (10)	C12—N1—C13—S1	−4.36 (13)
O2—C4—C5—C6	174.89 (10)	C14—N1—C13—S1	−169.35 (8)
C3—C4—C5—C6	−2.27 (16)	C11—S1—C13—O5	−176.90 (11)
O3—C5—C6—C1	179.79 (10)	C11—S1—C13—N1	3.80 (9)
C4—C5—C6—C1	−0.06 (17)	C13—N1—C14—C15	85.05 (12)
C2—C1—C6—C5	2.08 (17)	C12—N1—C14—C15	−79.20 (12)
C10—C1—C6—C5	178.78 (10)	N1—C14—C15—O6	−0.64 (14)
C6—C1—C10—C11	167.88 (12)	N1—C14—C15—C16	−179.20 (9)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and S1/N1/C11–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O6ⁱ	0.942 (14)	2.398 (14)	3.3108 (14)	163.2 (12)
C7—H7A···O5ⁱⁱ	0.971 (15)	2.482 (15)	3.4434 (15)	170.4 (13)
C14—H14A···O5ⁱⁱⁱ	1.016 (15)	2.335 (15)	3.2659 (14)	151.8 (11)
C7—H7C···Cg1^iv	0.994 (15)	2.755 (15)	3.5131 (14)	133.3 (11)
C9—H9C···Cg2ⁱ	1.001 (14)	2.900 (15)	3.8441 (14)	157.5 (11)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z; (iv) −x, −y+1, −z+1.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

Ashok, D. & Vanaja, B. (2016). Russ. J. Gen. Chem. 86, 681–685. CrossRef CAS Google Scholar
Barros, C. D., Amato, A. A., de Oliveira, T. B., Iannini, K. B. R., da Silva, A. L., da Silva, T. G., Leite, E. S., Hernandes, M. Z., Lima, M., de do, C. A. & Galdino, S. L. (2010). Bioorg. Med. Chem. 18, 3805–3811. CrossRef CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Koppireddi, S., Komsani, J. R., Avula, S., Pombala, S., Vasamsetti, S., Kotamraju, S. & Yadla, R. (2013). Eur. J. Med. Chem. 66, 305–313. CSD CrossRef CAS Google Scholar
Leite, F. H. A., Santiago, P. B. G. da S., Froes, T. Q., da Silva Filho, J., da Silva, S. G., Ximenes, R. M., de Faria, A. R., Brondani, D. J., de Albuquerque, J. F. C. & Castilho, M. S. (2016). Eur. J. Med. Chem. 123, 639–648. CrossRef CAS Google Scholar
Liu, X.-F., Zheng, C.-J., Sun, L.-P., Liu, X.-K. & Piao, H.-R. (2011). Eur. J. Med. Chem. 46, 3469–3473. Web of Science CrossRef CAS PubMed Google Scholar
Oakes, N. D., Kennedy, C. J., Jenkins, A. B., Laybutt, D. R., Chisholm, D. J. & Kraegen, E. W. (1994). Diabetes, 43, 1203–1210. CrossRef CAS Google Scholar
Sharma, R. K., Younis, Y., Mugumbate, G., Njoroge, M., Gut, J., Rosenthal, P. J. & Chibale, K. (2015). Eur. J. Med. Chem. 90, 507–518. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wei, S., Yang, J., Lee, S.-L., Kulp, S. K. & Chen, C.-S. (2009). Cancer Lett. 276, 119–124. CrossRef CAS Google Scholar
Xia, Z., Knaak, C., Ma, J., Beharry, Z. M., McInnes, C., Wang, W., Kraft, A. S. & Smith, C. D. (2009). J. Med. Chem. 52, 74–86. CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.