N-[2-(4-Bromo­phen­yl)-5-methyl-4-oxo-1,3-thia­zolidin-3-yl]pyridine-3-carboxamide

Akkurt, M.; Çelik, Í.; Demir, H.; Özkırımlı, S.; Büyükgüngör, O.

doi:10.1107/S1600536811009603

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o914-o915

doi:10.1107/S1600536811009603

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N-[2-(4-Bromophenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide

Mehmet Akkurt,^a ^* Ísmail Çelik,^b Hale Demir,^c Sumru Özkırımlı ^c and Orhan Büyükgüngör ^d

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, 34116 Beyazit, Istanbul, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 7 March 2011; accepted 14 March 2011; online 19 March 2011)

In the title compound, C₁₆H₁₄BrN₃O₂S, the atoms of the 1,3-thiazolidine group, except for the N and the C atoms attached to the bromobenzene ring, are disordered over two sets of sites with occupancies of 0.605 (13) and 0.395 (13). The benzene and pyridine rings make a dihedral angle of 86.2 (2)°. In the crystal, molecules are linked by intermolecular N—H⋯N and C—H⋯O hydrogen bonds, forming a three-dimensional network. Furthermore, there is a π–π stacking interaction [centroid–centroid distance = 3.758 (2) Å] between the pyridine and benzene rings.

Related literature

For the diverse pharmacological properties of pyridine-3-carboxamides, see: Abdel-Alim et al. (2005 ); Girgis et al. (2006 ); Slominska et al. (2008 ); Spanka et al. (2010 ); activities. For the pharmacological properties of 4-thiazolidinone derivatives, see: Vigorita et al. (1992 ); Barreca et al. (2003 ); Rao et al. (2004 ); Jacop & Kutty (2004 ); Kalia et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₄BrN₃O₂S
M_r = 392.27
Tetragonal, I 4₁ /a
a = 24.5799 (8) Å
c = 10.9601 (6) Å
V = 6621.8 (5) Å³
Z = 16
Mo Kα radiation
μ = 2.62 mm⁻¹
T = 296 K
0.37 × 0.30 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.444, T_max = 0.527
13377 measured reflections
3644 independent reflections
1834 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.119
S = 1.02
3644 reflections
259 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—HN2⋯N3ⁱ	0.861 (19)	2.05 (2)	2.899 (5)	167 (4)
C1—H1⋯O2ⁱⁱ	0.93	2.47	3.295 (5)	149
C15—H15⋯O1Aⁱⁱⁱ	0.93	2.38	3.062 (16)	130
Symmetry codes: (i) $[y+{\script{1\over 4}}, -x+{\script{3\over 4}}, -z+{\script{3\over 4}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, -y+{\script{1\over 2}}, z]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009603/om2414sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009603/om2414Isup2.hkl

checkCIF report

Comment top

Pyridine-3-carboxamides have gained attention because of their diverse pharmacological properties such as anti-inflammatory (Abdel-Alim et al., 2005), anticancer (Girgis et al. 2006), cytoprotective (Slominska et al., 2008), and anxiolytic (Spanka et al., 2010) activities. 4-Thiazolidinone derivatives have antineoplastic (Vigorita et al., 1992), HIV-1 RT inhibitory (Barreca et al., 2003; Rao et al., 2004), hypolipidemic (Jacop & Kutty, 2004), and anti-inflammatory (Kalia et al., 2007) activities. In an effort to evaluate bioactive molecules bearing both 4-thiazolidinone and pyridine-3-carboxamide scaffolds together, we synthesized N-(thiazolidin-3-yl)pyridine-3-carboxamide derivatives to examine their antiviral and anticancer properties.

In the 1,3-thiazolidine group of the title molecule (Fig. 1), all except the N1 and C7 atoms are disordered. The dihedral angle between the ring planes (S1A/N1/C7/C8A/C9A and S1B/N1/C7/C8B/C9B) formed by the major and minor disorder components is 18.5 (8) °.

The benzene (C1–C6) and pyridine (N3/C12–C16) rings make a dihedral angle of 86.21 (19) ° with each other. The N1—N2—C11—C12, N1—N2—C11—O2, N2—C11—C12—C13 and O2—C11—C12—C13 torsion angles are 180.0 (3), 1.2 (6), 172.2 (3) and -9.0 (6)°, respectively.

The molecular structure has two weak intramolecular C—H···N interactions (Table 1), generating S(5) ring motifs, and the crystal structure is stabilized by intermolecular N—H···N and C—H···O hydrogen bonds (Table 1 and Fig. 2). In addition, a π-π stacking interaction is observed [Cg3···Cg4(1/4 + y, 1/4 - x, 1/4 + z) = 3.758 (2) Å, where Cg3 and Cg4 are the centroids of the pyridine N3/C12–C16 and benzene C1–C6 rings, respectively].

Related literature top

For the diverse pharmacological properties of pyridine-3-carboxamides, see: Abdel-Alim et al. (2005); Girgis et al. (2006); Slominska et al. (2008); Spanka et al. (2010); activities. For the pharmacological properties of 4-thiazolidinone derivatives, see: Vigorita et al. (1992); Barreca et al. (2003); Rao et al. (2004); Jacop & Kutty (2004); Kalia et al. (2007).

Experimental top

N'-(4-bromobenzylidine)pyridine-3-carbohydrazide (0.01 mol) was reacted with 0.028 mol of 2-mercaptopropanoic acid in anhydrous benzene for 7 h using a Dean-Stark trap. Excess benzene was removed under reduced pressure. The residue was triturated with saturated sodium bicarbonate solution. The separated solid was filtered, washed with water and crystallized from methanol to yield white crystalline N-[5-methyl-2-(4-bromophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide. Yield: 58.92%; m.p.: 466.0–470.0 K. UV (EtOH) λ max: 203.0, 220.6, 262.0 nm. IR (KBr) υ: 1674 (amide C=O), 1727 (thia C=O) cm^-1; ¹H-NMR (DMSO-d₆, 500 MHz): 1.54, 1.55 (3H, 2 d, J=7.0 Hz, 6.8 Hz, CH₃-thia.), 4.12, 4.22 (1H, 2q, J=6.8 Hz, 6.8 Hz, H5-thia.), 5.90 (1H, s, H2-thia), 7.44–7.46 (2H, m, 2-C₆H₄-(H2,6)-thia.), 7.49–7.56 (1H, m, H5-pyridine), 7.57–7.60 (2H, m, 2-C₆H₄-(H3,5)-thia.), 8.05–8.09 (1H, m, H4-pyridine), 8.72–8.73 (1H, m, H6-pyridine), 8.86 (1H, 2 t, J=1 Hz, H2-pyridine), 10.94, 10.95 (1H, 2 s, CONH) p.p.m.; ESI– (m/z, relative abundance): 392.0 ([M—H+2]^-, 100), 390.01 ([M—H]^-, 79.69). Analysis calculated for C₁₆H₁₄BrN₃O₂S: C 48.99, H 3.60, N 10.71%. Found: C 49.03, H 3.54, N 10.58%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Only the major component of the disorder is shown.
	Fig. 2. The packing and hydrogen bonding interactions viewed down the c axis. All hydrogen atoms not involved in hydrogen bonding and the minor component of the disorder have been omitted for clarity.

N-[2-(4-Bromophenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]pyridine-3- carboxamide top

Crystal data top

C₁₆H₁₄BrN₃O₂S	D_x = 1.574 Mg m⁻³
M_r = 392.27	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 9828 reflections
Hall symbol: -I 4ad	θ = 1.7–27.6°
a = 24.5799 (8) Å	µ = 2.62 mm⁻¹
c = 10.9601 (6) Å	T = 296 K
V = 6621.8 (5) Å³	Block, colourless
Z = 16	0.37 × 0.30 × 0.28 mm
F(000) = 3168

Data collection top

Stoe IPDS 2 diffractometer	3644 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1834 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.055
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.1°, θ_min = 1.7°
ω scans	h = −31→21
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −31→31
T_min = 0.444, T_max = 0.527	l = −14→9
13377 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.046P)²] where P = (F_o² + 2F_c²)/3
3644 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.39 e Å⁻³
13 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₁₄BrN₃O₂S	Z = 16
M_r = 392.27	Mo Kα radiation
Tetragonal, I4₁/a	µ = 2.62 mm⁻¹
a = 24.5799 (8) Å	T = 296 K
c = 10.9601 (6) Å	0.37 × 0.30 × 0.28 mm
V = 6621.8 (5) Å³

Data collection top

Stoe IPDS 2 diffractometer	3644 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1834 reflections with I > 2σ(I)
T_min = 0.444, T_max = 0.527	R_int = 0.055
13377 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	13 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.39 e Å⁻³
3644 reflections	Δρ_min = −0.34 e Å⁻³
259 parameters

Special details top

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 e.s.d.'s 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 > σ(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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.16970 (2)	0.06678 (2)	0.30959 (7)	0.1147 (3)
S1A	0.2142 (3)	0.3258 (3)	0.5735 (10)	0.112 (3)	0.605 (13)
O1A	0.3622 (6)	0.3685 (8)	0.529 (2)	0.106 (7)	0.605 (13)
O2	0.36844 (13)	0.25700 (14)	0.7196 (3)	0.0950 (14)
N1	0.31204 (11)	0.29058 (12)	0.5238 (3)	0.0623 (13)
N2	0.35645 (13)	0.25553 (13)	0.5165 (3)	0.0595 (11)
N3	0.48519 (14)	0.14473 (13)	0.4828 (4)	0.0707 (14)
C1	0.20330 (14)	0.18614 (15)	0.5608 (4)	0.0640 (14)
C2	0.18240 (16)	0.14118 (16)	0.5027 (5)	0.0730 (16)
C3	0.19861 (16)	0.12919 (15)	0.3869 (5)	0.0673 (18)
C4	0.23459 (18)	0.16225 (18)	0.3269 (4)	0.0763 (17)
C5	0.25484 (16)	0.20793 (16)	0.3847 (4)	0.0653 (16)
C6	0.23981 (14)	0.22004 (14)	0.5022 (4)	0.0560 (14)
C7	0.26058 (14)	0.26964 (15)	0.5686 (4)	0.0703 (16)
C8A	0.2692 (4)	0.3725 (3)	0.5910 (13)	0.075 (4)	0.605 (13)
C9A	0.3197 (5)	0.3447 (3)	0.548 (2)	0.079 (8)	0.605 (13)
C10A	0.2598 (5)	0.4271 (4)	0.5333 (15)	0.125 (7)	0.605 (13)
C11	0.38243 (15)	0.24133 (15)	0.6199 (5)	0.0603 (14)
C12	0.42975 (14)	0.20345 (14)	0.6039 (4)	0.0510 (14)
C13	0.46220 (17)	0.19258 (16)	0.7037 (4)	0.0673 (16)
C14	0.50564 (16)	0.15811 (16)	0.6913 (5)	0.0713 (18)
C15	0.51542 (16)	0.13554 (16)	0.5804 (5)	0.0663 (16)
C16	0.44267 (16)	0.17785 (16)	0.4962 (4)	0.0630 (14)
O1B	0.3661 (9)	0.3633 (10)	0.482 (3)	0.077 (6)	0.395 (13)
C8B	0.2702 (5)	0.3783 (5)	0.5205 (14)	0.063 (5)	0.395 (13)
S1B	0.2171 (4)	0.3287 (4)	0.5249 (11)	0.078 (2)	0.395 (13)
C10B	0.2737 (7)	0.4152 (8)	0.6288 (16)	0.100 (7)	0.395 (13)
C9B	0.3209 (8)	0.3454 (4)	0.508 (3)	0.059 (7)	0.395 (13)
H5	0.27890	0.23070	0.34360	0.0780*
H7	0.26680	0.25850	0.65330	0.0840*
H4	0.24530	0.15400	0.24770	0.0910*
H10A	0.22620	0.44200	0.56260	0.1870*	0.605 (13)
H10B	0.25810	0.42300	0.44630	0.1870*	0.605 (13)
H8A	0.27360	0.37870	0.67870	0.07 (2)*	0.605 (13)
H13	0.45460	0.20850	0.77870	0.0810*
H14	0.52800	0.15030	0.75750	0.0850*
H15	0.54510	0.11230	0.57270	0.0800*
H16	0.42050	0.18400	0.42880	0.0760*
H1	0.19280	0.19380	0.64040	0.0770*
HN2	0.3657 (17)	0.2533 (17)	0.4409 (14)	0.0810*
H10C	0.28920	0.45110	0.55420	0.1870*	0.605 (13)
H2A	0.15730	0.11910	0.54230	0.0870*
H8B	0.26570	0.40050	0.44690	0.0750*	0.395 (13)
H10D	0.24060	0.43570	0.63580	0.1500*	0.395 (13)
H10E	0.30370	0.43980	0.61860	0.1500*	0.395 (13)
H10F	0.27900	0.39400	0.70120	0.1500*	0.395 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1245 (5)	0.0791 (3)	0.1405 (6)	−0.0194 (3)	−0.0237 (4)	−0.0275 (3)
S1A	0.0607 (18)	0.092 (3)	0.183 (8)	−0.0045 (15)	0.027 (3)	−0.069 (3)
O1A	0.066 (5)	0.084 (5)	0.167 (19)	−0.012 (4)	0.003 (7)	−0.028 (8)
O2	0.094 (2)	0.131 (3)	0.060 (2)	0.0395 (19)	0.0025 (17)	−0.029 (2)
N1	0.0498 (17)	0.0572 (18)	0.080 (3)	0.0016 (14)	0.0006 (16)	−0.0031 (17)
N2	0.0555 (18)	0.071 (2)	0.052 (2)	0.0053 (15)	0.0044 (18)	−0.0008 (19)
N3	0.076 (2)	0.074 (2)	0.062 (3)	0.0162 (18)	0.013 (2)	0.0013 (19)
C1	0.060 (2)	0.070 (2)	0.062 (3)	0.0051 (19)	0.014 (2)	−0.001 (2)
C2	0.061 (2)	0.059 (2)	0.099 (4)	−0.0032 (19)	0.004 (3)	0.009 (2)
C3	0.069 (3)	0.055 (2)	0.078 (4)	0.0041 (19)	−0.010 (2)	−0.005 (2)
C4	0.090 (3)	0.082 (3)	0.057 (3)	−0.004 (2)	0.002 (2)	−0.010 (3)
C5	0.070 (3)	0.068 (2)	0.058 (3)	−0.0105 (19)	0.004 (2)	0.003 (2)
C6	0.051 (2)	0.057 (2)	0.060 (3)	0.0035 (17)	0.003 (2)	−0.005 (2)
C7	0.059 (2)	0.077 (3)	0.075 (3)	−0.0095 (18)	0.009 (2)	−0.016 (2)
C8A	0.083 (6)	0.065 (6)	0.076 (10)	0.000 (4)	0.005 (7)	−0.012 (6)
C9A	0.050 (7)	0.076 (8)	0.11 (2)	−0.008 (5)	−0.009 (6)	−0.003 (5)
C10A	0.139 (9)	0.073 (7)	0.162 (16)	0.020 (6)	−0.004 (9)	−0.001 (8)
C11	0.061 (2)	0.067 (2)	0.053 (3)	0.0035 (18)	0.004 (2)	−0.007 (2)
C12	0.057 (2)	0.053 (2)	0.043 (3)	−0.0029 (16)	0.0041 (19)	−0.0006 (18)
C13	0.082 (3)	0.069 (2)	0.051 (3)	0.004 (2)	−0.006 (2)	−0.007 (2)
C14	0.070 (3)	0.066 (2)	0.078 (4)	0.008 (2)	−0.017 (2)	0.000 (3)
C15	0.061 (2)	0.060 (2)	0.078 (4)	0.0060 (18)	0.007 (2)	0.002 (2)
C16	0.070 (2)	0.070 (2)	0.049 (3)	0.012 (2)	0.003 (2)	−0.002 (2)
O1B	0.073 (8)	0.063 (9)	0.096 (14)	−0.008 (6)	0.006 (7)	0.010 (9)
C8B	0.072 (7)	0.063 (8)	0.053 (10)	0.008 (5)	0.001 (8)	0.012 (8)
S1B	0.049 (3)	0.069 (3)	0.115 (6)	0.0113 (17)	0.007 (3)	−0.030 (3)
C10B	0.110 (11)	0.078 (11)	0.112 (15)	−0.013 (8)	−0.001 (10)	−0.020 (11)
C9B	0.069 (12)	0.057 (10)	0.052 (14)	0.006 (8)	−0.001 (7)	−0.004 (6)

Geometric parameters (Å, º) top

Br1—C3	1.891 (4)	C8B—C9B	1.49 (2)
S1A—C7	1.791 (8)	C8B—C10B	1.50 (2)
S1A—C8A	1.784 (12)	C11—C12	1.500 (5)
S1B—C7	1.865 (11)	C12—C13	1.380 (6)
S1B—C8B	1.787 (16)	C12—C16	1.375 (6)
O1A—C9A	1.22 (2)	C13—C14	1.370 (6)
O1B—C9B	1.23 (3)	C14—C15	1.358 (7)
O2—C11	1.209 (6)	C1—H1	0.9300
N1—C9A	1.370 (9)	C2—H2A	0.9300
N1—N2	1.393 (4)	C4—H4	0.9300
N1—C7	1.451 (5)	C5—H5	0.9300
N1—C9B	1.376 (11)	C7—H7	0.9800
N2—C11	1.347 (6)	C8A—H8A	0.9800
N3—C15	1.322 (6)	C8B—H8B	0.9800
N3—C16	1.333 (5)	C10A—H10B	0.9600
N2—HN2	0.861 (19)	C10A—H10C	0.9600
C1—C6	1.383 (5)	C10A—H10A	0.9600
C1—C2	1.375 (6)	C10B—H10F	0.9600
C2—C3	1.363 (7)	C10B—H10D	0.9600
C3—C4	1.369 (6)	C10B—H10E	0.9600
C4—C5	1.382 (6)	C13—H13	0.9300
C5—C6	1.372 (6)	C14—H14	0.9300
C6—C7	1.509 (5)	C15—H15	0.9300
C8A—C9A	1.493 (16)	C16—H16	0.9300
C8A—C10A	1.502 (14)

Br1···C2ⁱ	3.679 (4)	C14···C1^vii	3.483 (6)
Br1···C3ⁱ	3.669 (4)	C15···O1Aⁱⁱⁱ	3.062 (16)
S1B···C15ⁱ	3.651 (12)	C15···O1Bⁱⁱⁱ	3.11 (2)
S1B···C14ⁱ	3.679 (11)	C15···S1B^vii	3.651 (12)
S1A···H14ⁱ	3.1300	C16···O1B^vi	3.23 (3)
S1B···H15ⁱ	3.0700	C5···H5ⁱⁱ	3.0400
S1B···H14ⁱ	3.1500	C5···HN2	3.01 (4)
S1B···H4ⁱⁱ	3.1600	C8B···H10E^viii	3.0800
O1A···N2	2.78 (2)	C8B···H4ⁱⁱ	3.0700
O1A···C15ⁱⁱⁱ	3.062 (16)	C10A···H10C^viii	3.0100
O1A···C11	3.32 (2)	C11···H7	2.9000
O1B···N2	2.69 (2)	C15···HN2^vi	3.048 (18)
O1B···C11	3.38 (3)	C16···HN2	2.72 (4)
O1B···C16^iv	3.23 (3)	C16···HN2^vi	2.88 (3)
O1B···C15ⁱⁱⁱ	3.11 (2)	H1···O2^v	2.4700
O2···N1	2.685 (5)	H1···H7	2.4200
O2···C7	3.141 (5)	HN2···C16	2.72 (4)
O2···C9A	3.102 (15)	HN2···H16	2.1800
O2···C1^v	3.295 (5)	HN2···C5	3.01 (4)
O2···C9B	3.39 (2)	HN2···N3^iv	2.05 (2)
O1A···H15ⁱⁱⁱ	2.3800	HN2···C15^iv	3.048 (18)
O1A···H10C	2.7200	HN2···O1B	2.74 (5)
O1B···H10E	2.8500	HN2···C16^iv	2.88 (3)
O1B···H15ⁱⁱⁱ	2.4700	HN2···H5	2.4500
O1B···HN2	2.74 (5)	H4···S1Bⁱⁱ	3.1600
O1B···H16^iv	2.5700	H4···H8Bⁱⁱ	2.5300
O2···H1^v	2.4700	H4···C8Bⁱⁱ	3.0700
O2···H7	2.6000	H5···C5ⁱⁱ	3.0400
O2···H13	2.5200	H5···HN2	2.4500
N1···O2	2.685 (5)	H5···N1	2.5900
N2···N3^iv	2.899 (5)	H5···N2	2.7600
N2···O1A	2.78 (2)	H7···C11	2.9000
N2···C5	3.113 (5)	H7···H1	2.4200
N2···O1B	2.69 (2)	H7···O2	2.6000
N3···N2^vi	2.899 (5)	H7···H7^v	2.3100
N1···H5	2.5900	H8B···H10E^viii	2.3400
N2···H16	2.5500	H8B···H4ⁱⁱ	2.5300
N2···H5	2.7600	H10B···H10C^viii	2.2900
N3···HN2^vi	2.05 (2)	H10C···O1A	2.7200
N3···H16^vi	2.7400	H10C···H10B^ix	2.2900
C1···C14ⁱ	3.483 (6)	H10C···C10A^ix	3.0100
C1···O2^v	3.295 (5)	H10E···C8B^ix	3.0800
C2···C13ⁱ	3.574 (6)	H10E···O1B	2.8500
C2···Br1^vii	3.679 (4)	H10E···H8B^ix	2.3400
C3···Br1^vii	3.669 (4)	H13···O2	2.5200
C5···N2	3.113 (5)	H14···S1A^vii	3.1300
C7···O2	3.141 (5)	H14···S1B^vii	3.1500
C9A···O2	3.102 (15)	H15···O1Bⁱⁱⁱ	2.4700
C9B···O2	3.39 (2)	H15···S1B^vii	3.0700
C11···O1A	3.32 (2)	H15···O1Aⁱⁱⁱ	2.3800
C11···O1B	3.38 (3)	H16···N2	2.5500
C13···C13ⁱⁱⁱ	3.380 (6)	H16···N3^iv	2.7400
C13···C2^vii	3.574 (6)	H16···O1B^vi	2.5700
C14···S1B^vii	3.679 (11)	H16···HN2	2.1800

C7—S1A—C8A	91.0 (4)	C11—C12—C13	118.4 (4)
C7—S1B—C8B	96.9 (6)	C12—C13—C14	119.5 (4)
N2—N1—C9A	120.3 (6)	C13—C14—C15	118.7 (4)
N2—N1—C9B	118.3 (9)	N3—C15—C14	123.7 (4)
C7—N1—C9A	113.5 (7)	N3—C16—C12	123.7 (4)
C7—N1—C9B	121.9 (9)	C2—C1—H1	120.00
N2—N1—C7	118.9 (3)	C6—C1—H1	120.00
N1—N2—C11	118.9 (3)	C1—C2—H2A	120.00
C15—N3—C16	117.1 (4)	C3—C2—H2A	120.00
C11—N2—HN2	132 (3)	C3—C4—H4	120.00
N1—N2—HN2	108 (3)	C5—C4—H4	120.00
C2—C1—C6	120.8 (4)	C4—C5—H5	120.00
C1—C2—C3	119.7 (4)	C6—C5—H5	120.00
Br1—C3—C4	120.6 (4)	S1A—C7—H7	107.00
Br1—C3—C2	118.9 (3)	N1—C7—H7	106.00
C2—C3—C4	120.5 (4)	C6—C7—H7	106.00
C3—C4—C5	119.7 (4)	S1B—C7—H7	123.00
C4—C5—C6	120.6 (4)	S1A—C8A—H8A	107.00
C1—C6—C7	118.9 (4)	C9A—C8A—H8A	107.00
C1—C6—C5	118.7 (4)	C10A—C8A—H8A	107.00
C5—C6—C7	122.5 (3)	C9B—C8B—H8B	109.00
N1—C7—C6	114.7 (3)	C10B—C8B—H8B	109.00
S1A—C7—C6	115.0 (4)	S1B—C8B—H8B	109.00
S1B—C7—N1	97.9 (4)	C8A—C10A—H10C	109.00
S1B—C7—C6	108.1 (4)	H10A—C10A—H10B	110.00
S1A—C7—N1	107.0 (4)	H10B—C10A—H10C	110.00
S1A—C8A—C9A	107.6 (7)	C8A—C10A—H10B	109.00
C9A—C8A—C10A	113.8 (11)	H10A—C10A—H10C	109.00
S1A—C8A—C10A	114.4 (9)	C8A—C10A—H10A	109.00
S1B—C8B—C10B	115.7 (11)	H10D—C10B—H10F	110.00
C9B—C8B—C10B	110.7 (15)	C8B—C10B—H10D	109.00
S1B—C8B—C9B	104.1 (9)	C8B—C10B—H10E	109.00
N1—C9A—C8A	113.0 (8)	C8B—C10B—H10F	110.00
O1A—C9A—C8A	123.3 (11)	H10D—C10B—H10E	109.00
O1A—C9A—N1	123.6 (14)	H10E—C10B—H10F	110.00
N1—C9B—C8B	112.8 (14)	C14—C13—H13	120.00
O1B—C9B—C8B	125.6 (15)	C12—C13—H13	120.00
O1B—C9B—N1	121.5 (17)	C15—C14—H14	121.00
O2—C11—N2	122.9 (4)	C13—C14—H14	121.00
O2—C11—C12	121.6 (4)	N3—C15—H15	118.00
N2—C11—C12	115.5 (4)	C14—C15—H15	118.00
C13—C12—C16	117.3 (3)	C12—C16—H16	118.00
C11—C12—C16	124.3 (4)	N3—C16—H16	118.00

C8A—S1A—C7—N1	−26.3 (7)	C2—C3—C4—C5	0.4 (6)
C8A—S1A—C7—C6	−154.9 (6)	Br1—C3—C4—C5	179.4 (3)
C7—S1A—C8A—C9A	19.9 (12)	C3—C4—C5—C6	0.9 (6)
C7—S1A—C8A—C10A	147.4 (10)	C4—C5—C6—C7	−179.6 (4)
C7—N1—N2—C11	−75.1 (4)	C4—C5—C6—C1	−1.1 (6)
C9A—N1—N2—C11	73.1 (11)	C5—C6—C7—N1	−24.1 (5)
C9A—N1—C7—S1A	26.8 (10)	C5—C6—C7—S1A	100.6 (5)
N2—N1—C7—C6	−54.3 (5)	C1—C6—C7—N1	157.4 (3)
C9A—N1—C7—C6	155.5 (9)	C1—C6—C7—S1A	−77.9 (5)
C7—N1—C9A—C8A	−12.1 (17)	C10A—C8A—C9A—N1	−136.2 (13)
N2—N1—C9A—O1A	23 (3)	S1A—C8A—C9A—N1	−8.3 (18)
C7—N1—C9A—O1A	172.4 (18)	C10A—C8A—C9A—O1A	39 (3)
N2—N1—C9A—C8A	−161.9 (10)	S1A—C8A—C9A—O1A	167 (2)
N2—N1—C7—S1A	177.0 (4)	N2—C11—C12—C13	172.2 (3)
N1—N2—C11—O2	1.2 (6)	O2—C11—C12—C13	−9.0 (6)
N1—N2—C11—C12	180.0 (3)	O2—C11—C12—C16	169.8 (4)
C16—N3—C15—C14	−0.5 (6)	N2—C11—C12—C16	−9.0 (5)
C15—N3—C16—C12	1.6 (6)	C16—C12—C13—C14	1.0 (6)
C2—C1—C6—C7	178.5 (3)	C11—C12—C16—N3	179.2 (4)
C2—C1—C6—C5	0.0 (6)	C11—C12—C13—C14	180.0 (4)
C6—C1—C2—C3	1.3 (6)	C13—C12—C16—N3	−1.9 (6)
C1—C2—C3—C4	−1.5 (6)	C12—C13—C14—C15	−0.1 (6)
C1—C2—C3—Br1	179.5 (3)	C13—C14—C15—N3	−0.2 (6)

Symmetry codes: (i) −y+1/4, x−1/4, z−1/4; (ii) −x+1/2, −y+1/2, −z+1/2; (iii) −x+1, −y+1/2, z; (iv) y+1/4, −x+3/4, −z+3/4; (v) −x+1/2, −y+1/2, −z+3/2; (vi) −y+3/4, x−1/4, −z+3/4; (vii) y+1/4, −x+1/4, z+1/4; (viii) y−1/4, −x+3/4, z−1/4; (ix) −y+3/4, x+1/4, z+1/4.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···N3^iv	0.861 (19)	2.05 (2)	2.899 (5)	167 (4)
C1—H1···O2^v	0.93	2.47	3.295 (5)	149
C5—H5···N1	0.93	2.59	2.903 (5)	100
C15—H15···O1Aⁱⁱⁱ	0.93	2.38	3.062 (16)	130
C16—H16···N2	0.93	2.55	2.861 (5)	100

Symmetry codes: (iii) −x+1, −y+1/2, z; (iv) y+1/4, −x+3/4, −z+3/4; (v) −x+1/2, −y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄BrN₃O₂S
M_r	392.27
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	296
a, c (Å)	24.5799 (8), 10.9601 (6)
V (Å³)	6621.8 (5)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	2.62
Crystal size (mm)	0.37 × 0.30 × 0.28

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.444, 0.527
No. of measured, independent and observed [I > 2σ(I)] reflections	13377, 3644, 1834
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.119, 1.02
No. of reflections	3644
No. of parameters	259
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.34

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN2···N3ⁱ	0.861 (19)	2.05 (2)	2.899 (5)	167 (4)
C1—H1···O2ⁱⁱ	0.93	2.47	3.295 (5)	149
C15—H15···O1Aⁱⁱⁱ	0.93	2.38	3.062 (16)	130

Symmetry codes: (i) y+1/4, −x+3/4, −z+3/4; (ii) −x+1/2, −y+1/2, −z+3/2; (iii) −x+1, −y+1/2, z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). This work was supported by the Scientific Research Projects Coordination Unit of Istanbul University (project No. T-3691).

References

Abdel-Alim, A. M., El-Shorbagi, A. A., Abdel-Mothy, S. G. & Abdel-Allah, H. H. M. (2005). Arch. Pharm. Res. 28, 637–647. Web of Science PubMed CAS Google Scholar
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Volume 67| Part 4| April 2011| Pages o914-o915

doi:10.1107/S1600536811009603

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[2-(4-Bromo­phen­yl)-5-methyl-4-oxo-1,3-thia­zolidin-3-yl]pyridine-3-carboxamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[2-(4-Bromophenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide