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

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

doi:10.1107/S1600536810022506

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1691-o1692

doi:10.1107/S1600536810022506

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N-[(2S)-2-(4-Bromophenyl)-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 Arts and 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 June 2010; accepted 11 June 2010; online 18 June 2010)

In the title compound, C₁₅H₁₂BrN₃O₂S, the dihedral angle between the pyridine and benzene rings is 73.17 (19)°. The five-membered 1,3-thiazolidine ring has an envelope conformation, with the S atom displaced by 0.196 (1) Å from the mean plane of the four other ring atoms. An intramolecular C—H⋯N interaction occurs. The crystal structure is stabilized by intermolecular N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions. In addition, a weak π–π stacking interaction is also observed between the 1,3-thiazolidine and pyridine rings [centroid–centroid distance = 3.805 (2) Å].

Related literature

For the cytoprotective and antiviral properties of nicotinamide, see: Gaudineau & Auclair (2004 ); Moell et al. (2009 ). For 3-pyridinecarboxamide derivatives with antitumor activity, see: Elbaum et al. (2003 ). For the various biological activities of thiazolidinones, see: Capan et al. (1999 ) and Ozkırımlı et al. (2009 ) (antifungal); Guzel et al. (2006 ) (antituberculosis); Rawal et al. (2007 ) (RT Inhibitor); Vanderlinden et al. (2010 ) (antiviral). For standard bond-length data, see: Allen et al. (1987 ). For puckering and asymmetry parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₂BrN₃O₂S
M_r = 378.25
Trigonal, $[R \overline 3]$
a = 24.9588 (9) Å
c = 12.8013 (5) Å
V = 6906.1 (4) Å³
Z = 18
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 296 K
0.28 × 0.23 × 0.19 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.505, T_max = 0.616
13554 measured reflections
3174 independent reflections
1963 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.085
S = 0.95
3174 reflections
202 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.85 (3)	2.07 (3)	2.914 (4)	172 (4)
C3—H3⋯O2ⁱ	0.93	2.43	3.237 (5)	146
C15—H15⋯N2	0.93	2.54	2.864 (5)	101
C15—H15⋯O1ⁱ	0.93	2.50	3.399 (5)	162
C14—H14⋯Cg3ⁱⁱ	0.93	2.79	3.692 (4)	164
Symmetry codes: (i) $[-y+{\script{4\over 3}}, x-y+{\script{5\over 3}}, z-{\script{1\over 3}}]$ ; (ii) x+1, y, z+2.

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/S1600536810022506/lh5067sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022506/lh5067Isup2.hkl

checkCIF report

Comment top

Development of new active compounds for viral infections is a high priority goal. The rapid onset of resistance and hypersensitivity reactions limit the use of antiviral compounds and therefore, there is an ongoing need for novel antiviral agents. A number of diverse chemical structures have been shown to be potent RT Inhibitors. Nicotinamide is gaining attention for its cytoprotective and antiviral properties (Gaudineau et al., 2004). Antiviral effect of nicotinamide and its inhibitory effect on enterovirus induced chemokine secretion have been recently shown (Moell et al., 2009). Furthermore, 3-pyridinecarboxamide derivatives with antitumor activity have been reported (Elbaum et al., 2003). Thiazolidinones exhibit various biological activities such as antifungal (Capan et al., 1999; Ozkırımlı et al., 2009); antituberculosis (Guzel et al., 2006); RT Inhibitor (Rawal et al., 2007); antiviral (Vanderlinden et al., 2010). We combine these two moities as part of an ongoing project directed towards the design and synthesis of bioactive molecules bearing 4-thiazolidinone and pyridine-3-carboxamide scaffolds together.

In the title molecule (I) shown in Fig. 1, the bond lengths and the bond angles are in the normal ranges (Allen et al., 1987). The C2—C1—C7—N1, C2—C1—C7—S1, N1—N2—C10—O2 and N1—N2—C10—C11 torsion angles are 40.2 (4), -76.2 (3), -0.7 (5) and -179.7 (3) °, respectively. The dihedral angle between the pyridine (N3/C11–C15) and benzene (C1–C6) rings is 73.17 (19) °. The five-membered 1,3-thiazolidine ring has an envelope conformation, with atom S1 displaced by -0.196 (1) Å from the S1/N1/C7–C9 plane [the puckering parameters (Cremer & Pople, 1975) are Q₂ = 0.361 (3) Å and ϕ₂ = 188.0 (5) °].

The crystal structure is stabilized by intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2) and a C—H···π interactions (Table 1). A weak π-π stacking interaction is observed between the 1,3-thiazolidine and pyridine rings [Cg2···Cg2(2/3 - x, 7/3 - y, 1/3 - z) = 3.805 (2) Å, where Cg1 and Cg2 are the centroids of the S1/N1/C7–C9 1,3-thiazolidine and N3/C11–C15 pyridine rings, respectively].

Related literature top

For the cytoprotective and antiviral properties of nicotinamide, see: Gaudineau et al. (2004); Moell et al. (2009). For 3-pyridinecarboxamide derivatives with antitumor activity, see: Elbaum et al. (2003). For the various biological activities of thiazolidinones, see: Capan et al. (1999) and Ozkırımlı et al. (2009) (antifungal); Guzel et al. (2006) (antituberculosis); Rawal et al. (2007) (RT Inhibitor); Vanderlinden et al. (2010) (antiviral). For standard bond-length data, see: Allen et al. (1987). For puckering and asymmetry parameters, see: Cremer & Pople (1975).

Experimental top

0.01 mol of N'-(4-bromobenzylidine)pyridine-3-carbohydrazide was reacted with 0.03 mol of mercaptoacetic acid in anhydrous benzene for 8 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. White crystalline solid. Yield: 60.84%; m.p.: 446.1–450.0 K. UV (EtOH) max: 202.6, 221.2, 264.8 nm. IR (KBr) υ: 1666 (amide C=O), 1687 (thia C=O); ¹H-NMR (DMSO-d₆, 400 MHz): 3.80 (1H, d, J=16 Hz, H5-thia.), 3.95 (1H, dd, J=15.8, 2.8 Hz, H5-thia.), 5.92 (1H, s, H2-thia.), 7.46 (2H, d, J=8.4 Hz, 2-C₆H₄-(H2,6)-thia.), 7.47–7.49 (1H, m, H5-pyridine), 7.56 (1H, d, J=8.8 Hz, 2-C₆H₄-(H3,5)-thia.), 8.08 (1H, dt, J=8.4, 1.6, 1.6 Hz, H4-pyridine), 8.71 (1H, dd, J=4.6, 1.6 Hz, H6-pyridine), 8.87 (1H, d, J=1.6 Hz, H2-pyridine), 10.93 (1H, s, CONH); ESI+ (m/z): 380.23 ([MH+2]⁺, 100), 378.24([MH]⁺, 98.71). Analysis calculated for C₁₅H₁₂BrN₃O₂S: C 47.63, H 3.20, N 11.11%. Found: C 47.39, H 3.09, N 10.98%.

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.
	Fig. 2. View of the packing and hydrogen bonding interactions of (I). All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

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

Crystal data top

C₁₅H₁₂BrN₃O₂S	D_x = 1.637 Mg m⁻³
M_r = 378.25	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 10912 reflections
Hall symbol: -R 3	θ = 1.6–28.0°
a = 24.9588 (9) Å	µ = 2.82 mm⁻¹
c = 12.8013 (5) Å	T = 296 K
V = 6906.1 (4) Å³	Block, colourless
Z = 18	0.28 × 0.23 × 0.19 mm
F(000) = 3420

Data collection top

Stoe IPDS 2 diffractometer	3174 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1963 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.050
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.6°
ω scans	h = −30→27
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −31→31
T_min = 0.505, T_max = 0.616	l = −15→16
13554 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0375P)²] where P = (F_o² + 2F_c²)/3
3174 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₅H₁₂BrN₃O₂S	Z = 18
M_r = 378.25	Mo Kα radiation
Trigonal, R3	µ = 2.82 mm⁻¹
a = 24.9588 (9) Å	T = 296 K
c = 12.8013 (5) Å	0.28 × 0.23 × 0.19 mm
V = 6906.1 (4) Å³

Data collection top

Stoe IPDS 2 diffractometer	3174 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1963 reflections with I > 2σ(I)
T_min = 0.505, T_max = 0.616	R_int = 0.050
13554 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.22 e Å⁻³
3174 reflections	Δρ_min = −0.35 e Å⁻³
202 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
Br1	0.04324 (2)	0.93003 (2)	0.13333 (3)	0.0833 (2)
S1	0.18291 (4)	0.97254 (4)	0.63617 (6)	0.0594 (3)
O1	0.35556 (11)	1.03443 (11)	0.58153 (16)	0.0609 (9)
O2	0.33205 (10)	1.15286 (10)	0.51669 (15)	0.0561 (8)
N1	0.27161 (11)	1.03012 (11)	0.50268 (17)	0.0459 (8)
N2	0.30533 (11)	1.06767 (12)	0.41953 (17)	0.0456 (8)
N3	0.41259 (16)	1.17793 (16)	0.1703 (2)	0.0802 (13)
C1	0.16764 (13)	0.99737 (13)	0.4306 (2)	0.0403 (9)
C2	0.16483 (14)	0.95013 (14)	0.3696 (2)	0.0496 (11)
C3	0.12676 (15)	0.92888 (15)	0.2825 (2)	0.0533 (11)
C4	0.09162 (14)	0.95549 (15)	0.2568 (2)	0.0522 (11)
C5	0.09214 (14)	1.00079 (15)	0.3177 (2)	0.0534 (11)
C6	0.13042 (14)	1.02166 (14)	0.4045 (2)	0.0474 (10)
C7	0.21047 (13)	1.02331 (14)	0.5225 (2)	0.0444 (10)
C8	0.30194 (16)	1.02317 (14)	0.5850 (2)	0.0488 (11)
C9	0.26115 (15)	1.00121 (17)	0.6800 (2)	0.0610 (11)
C10	0.33513 (13)	1.13027 (15)	0.4341 (2)	0.0443 (10)
C11	0.37035 (14)	1.16854 (14)	0.3424 (2)	0.0451 (10)
C12	0.39270 (18)	1.23136 (16)	0.3450 (3)	0.0687 (14)
C13	0.4255 (2)	1.26670 (18)	0.2588 (3)	0.0816 (16)
C14	0.43328 (19)	1.2376 (2)	0.1757 (3)	0.0802 (17)
C15	0.38243 (17)	1.14490 (17)	0.2539 (3)	0.0653 (14)
H2	0.18870	0.93250	0.38740	0.0600*
H2A	0.3055 (19)	1.0477 (17)	0.366 (2)	0.1000*
H3	0.12500	0.89710	0.24190	0.0640*
H5	0.06710	1.01740	0.30110	0.0640*
H6	0.13100	1.05260	0.44590	0.0570*
H7	0.21550	1.06370	0.54110	0.0530*
H9A	0.27310	1.03500	0.72880	0.0730*
H9B	0.26480	0.96860	0.71470	0.0730*
H12	0.38610	1.24980	0.40290	0.0820*
H13	0.44160	1.30930	0.25830	0.0980*
H14	0.45490	1.26170	0.11850	0.0960*
H15	0.36840	1.10270	0.25250	0.0780*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0755 (3)	0.1114 (4)	0.0638 (2)	0.0473 (3)	−0.0204 (2)	−0.0167 (2)
S1	0.0544 (5)	0.0724 (6)	0.0463 (4)	0.0279 (5)	0.0077 (4)	0.0159 (4)
O1	0.0534 (15)	0.0774 (17)	0.0589 (13)	0.0380 (13)	−0.0050 (11)	0.0014 (11)
O2	0.0534 (14)	0.0621 (14)	0.0462 (12)	0.0240 (12)	0.0031 (9)	−0.0101 (10)
N1	0.0430 (14)	0.0531 (16)	0.0386 (12)	0.0218 (13)	0.0041 (11)	0.0096 (11)
N2	0.0462 (15)	0.0478 (16)	0.0370 (13)	0.0192 (13)	0.0057 (11)	0.0030 (11)
N3	0.095 (3)	0.068 (2)	0.0646 (18)	0.031 (2)	0.0335 (17)	0.0100 (16)
C1	0.0415 (17)	0.0418 (17)	0.0388 (14)	0.0217 (14)	0.0059 (12)	0.0077 (12)
C2	0.0474 (19)	0.052 (2)	0.0564 (17)	0.0300 (16)	0.0032 (14)	0.0058 (14)
C3	0.053 (2)	0.052 (2)	0.0570 (18)	0.0278 (17)	0.0042 (15)	−0.0056 (15)
C4	0.0463 (19)	0.058 (2)	0.0486 (16)	0.0233 (17)	0.0024 (14)	0.0021 (15)
C5	0.0477 (19)	0.056 (2)	0.0630 (19)	0.0309 (17)	−0.0008 (15)	0.0061 (16)
C6	0.0514 (19)	0.0434 (18)	0.0514 (16)	0.0268 (16)	0.0050 (14)	0.0040 (13)
C7	0.0421 (18)	0.0465 (18)	0.0456 (15)	0.0229 (15)	0.0027 (13)	0.0031 (13)
C8	0.058 (2)	0.0515 (19)	0.0404 (16)	0.0299 (17)	−0.0024 (14)	−0.0005 (13)
C9	0.064 (2)	0.076 (2)	0.0430 (17)	0.035 (2)	−0.0016 (15)	0.0114 (16)
C10	0.0359 (16)	0.053 (2)	0.0425 (16)	0.0212 (15)	−0.0028 (12)	−0.0033 (14)
C11	0.0401 (17)	0.0482 (19)	0.0452 (16)	0.0207 (15)	−0.0005 (13)	0.0004 (13)
C12	0.080 (3)	0.056 (2)	0.058 (2)	0.025 (2)	0.0008 (18)	−0.0047 (17)
C13	0.098 (3)	0.044 (2)	0.078 (3)	0.017 (2)	0.006 (2)	0.0110 (19)
C14	0.078 (3)	0.071 (3)	0.070 (3)	0.021 (2)	0.021 (2)	0.011 (2)
C15	0.076 (3)	0.057 (2)	0.0571 (19)	0.029 (2)	0.0231 (17)	0.0053 (17)

Geometric parameters (Å, º) top

Br1—C4	1.896 (3)	C5—C6	1.386 (4)
S1—C7	1.823 (3)	C8—C9	1.503 (4)
S1—C9	1.801 (4)	C10—C11	1.491 (4)
O1—C8	1.223 (5)	C11—C12	1.377 (5)
O2—C10	1.219 (3)	C11—C15	1.379 (5)
N1—N2	1.390 (3)	C12—C13	1.394 (6)
N1—C7	1.471 (5)	C13—C14	1.356 (6)
N1—C8	1.358 (4)	C2—H2	0.9300
N2—C10	1.366 (4)	C3—H3	0.9300
N3—C14	1.312 (6)	C5—H5	0.9300
N3—C15	1.331 (5)	C6—H6	0.9300
N2—H2A	0.85 (3)	C7—H7	0.9800
C1—C6	1.380 (5)	C9—H9A	0.9700
C1—C7	1.501 (4)	C9—H9B	0.9700
C1—C2	1.386 (4)	C12—H12	0.9300
C2—C3	1.387 (4)	C13—H13	0.9300
C3—C4	1.379 (5)	C14—H14	0.9300
C4—C5	1.368 (4)	C15—H15	0.9300

Br1···H5ⁱ	3.1900	C15···O1^vi	3.399 (5)
S1···C6ⁱⁱ	3.524 (4)	C1···H6ⁱⁱ	2.9800
S1···N3ⁱⁱⁱ	3.003 (3)	C2···H7ⁱⁱ	2.7800
S1···C14ⁱⁱⁱ	3.644 (5)	C3···H7ⁱⁱ	2.9100
S1···H6ⁱⁱ	3.0300	C4···H14^viii	3.0000
O1···N2	2.757 (4)	C5···H5ⁱ	3.0700
O1···C10	3.281 (4)	C5···H14^viii	2.9100
O1···N2^iv	2.914 (4)	C6···H14^viii	3.0100
O1···C2^iv	3.369 (4)	C6···H6ⁱⁱ	2.9700
O1···C15^iv	3.399 (6)	C8···H2A^iv	3.00 (6)
O2···C2^v	3.415 (6)	C10···H3^iv	2.9500
O2···C8	3.062 (4)	C10···H7	2.9300
O2···N1	2.659 (3)	C12···H9B^v	3.0200
O2···C7	3.140 (4)	C15···H2A	2.64 (4)
O2···C3^iv	3.237 (6)	H2···N1	2.7100
O1···H15^iv	2.5000	H2···O2ⁱⁱ	2.7500
O1···H2A^iv	2.07 (5)	H2A···C15	2.64 (4)
O2···H7	2.6500	H2A···H15	2.0700
O2···H2^v	2.7500	H2A···O1^vi	2.07 (3)
O2···H12	2.5600	H2A···C8^vi	3.00 (4)
O2···H3^iv	2.4300	H3···O2^vi	2.4300
N1···O2	2.659 (3)	H3···C10^vi	2.9500
N2···O1	2.757 (4)	H5···Br1^ix	3.1900
N2···C2	3.320 (4)	H5···C5^ix	3.0700
N2···O1^vi	2.914 (4)	H6···H7	2.3300
N3···C9^vii	3.262 (5)	H6···S1^v	3.0300
N3···S1^vii	3.003 (3)	H6···C1^v	2.9800
N1···H2	2.7100	H6···C6^v	2.9700
N2···H15	2.5400	H7···O2	2.6500
N3···H9B^vii	2.8500	H7···C10	2.9300
C2···N2	3.320 (4)	H7···H6	2.3300
C2···O2ⁱⁱ	3.415 (4)	H7···C2^v	2.7800
C2···O1^vi	3.369 (5)	H7···C3^v	2.9100
C3···O2^vi	3.237 (5)	H9B···C12ⁱⁱ	3.0200
C6···S1^v	3.524 (3)	H9B···N3ⁱⁱⁱ	2.8500
C7···O2	3.140 (4)	H12···O2	2.5600
C8···O2	3.062 (4)	H14···C4^viii	3.0000
C9···N3ⁱⁱⁱ	3.262 (5)	H14···C5^viii	2.9100
C10···O1	3.281 (4)	H14···C6^viii	3.0100
C14···S1^vii	3.644 (4)	H15···N2	2.5400
C14···C15^viii	3.507 (7)	H15···H2A	2.0700
C15···C14^viii	3.507 (7)	H15···O1^vi	2.5000

C7—S1—C9	90.87 (15)	C10—C11—C15	123.9 (3)
N2—N1—C7	117.0 (2)	C11—C12—C13	118.5 (3)
N2—N1—C8	119.5 (3)	C12—C13—C14	118.6 (4)
C7—N1—C8	117.6 (2)	N3—C14—C13	124.7 (4)
N1—N2—C10	117.8 (2)	N3—C15—C11	124.9 (3)
C14—N3—C15	116.1 (3)	C1—C2—H2	120.00
C10—N2—H2A	129 (2)	C3—C2—H2	120.00
N1—N2—H2A	114 (2)	C2—C3—H3	120.00
C2—C1—C7	122.0 (3)	C4—C3—H3	120.00
C2—C1—C6	118.6 (3)	C4—C5—H5	120.00
C6—C1—C7	119.4 (3)	C6—C5—H5	120.00
C1—C2—C3	120.8 (3)	C1—C6—H6	119.00
C2—C3—C4	119.1 (3)	C5—C6—H6	119.00
C3—C4—C5	121.1 (3)	S1—C7—H7	109.00
Br1—C4—C3	119.3 (2)	N1—C7—H7	109.00
Br1—C4—C5	119.6 (3)	C1—C7—H7	109.00
C4—C5—C6	119.2 (3)	S1—C9—H9A	110.00
C1—C6—C5	121.2 (3)	S1—C9—H9B	110.00
S1—C7—C1	112.7 (2)	C8—C9—H9A	110.00
S1—C7—N1	103.1 (2)	C8—C9—H9B	110.00
N1—C7—C1	112.9 (2)	H9A—C9—H9B	109.00
N1—C8—C9	110.8 (3)	C11—C12—H12	121.00
O1—C8—C9	125.3 (3)	C13—C12—H12	121.00
O1—C8—N1	123.9 (3)	C12—C13—H13	121.00
S1—C9—C8	107.2 (2)	C14—C13—H13	121.00
N2—C10—C11	115.8 (2)	N3—C14—H14	118.00
O2—C10—N2	121.6 (3)	C13—C14—H14	118.00
O2—C10—C11	122.7 (3)	N3—C15—H15	118.00
C12—C11—C15	117.2 (3)	C11—C15—H15	118.00
C10—C11—C12	118.9 (3)

C7—S1—C9—C8	−26.5 (3)	C7—C1—C2—C3	−177.2 (3)
C9—S1—C7—N1	29.0 (2)	C6—C1—C7—S1	104.9 (3)
C9—S1—C7—C1	151.0 (3)	C6—C1—C7—N1	−138.8 (3)
C7—N1—N2—C10	78.1 (4)	C1—C2—C3—C4	0.2 (5)
C8—N1—C7—S1	−26.4 (3)	C2—C3—C4—C5	−2.3 (5)
N2—N1—C7—C1	58.8 (3)	C2—C3—C4—Br1	176.3 (2)
N2—N1—C7—S1	−179.29 (19)	Br1—C4—C5—C6	−176.3 (2)
N2—N1—C8—O1	−19.3 (4)	C3—C4—C5—C6	2.4 (5)
C7—N1—C8—O1	−171.5 (3)	C4—C5—C6—C1	−0.3 (5)
N2—N1—C8—C9	159.6 (3)	O1—C8—C9—S1	−165.2 (3)
C7—N1—C8—C9	7.4 (4)	N1—C8—C9—S1	16.0 (3)
C8—N1—C7—C1	−148.3 (3)	N2—C10—C11—C12	169.1 (4)
C8—N1—N2—C10	−74.3 (4)	O2—C10—C11—C12	−9.9 (6)
N1—N2—C10—O2	−0.7 (5)	O2—C10—C11—C15	169.9 (4)
N1—N2—C10—C11	−179.7 (3)	N2—C10—C11—C15	−11.1 (6)
C14—N3—C15—C11	1.9 (7)	C15—C11—C12—C13	0.3 (6)
C15—N3—C14—C13	−0.6 (8)	C10—C11—C15—N3	178.5 (4)
C6—C1—C2—C3	1.8 (5)	C10—C11—C12—C13	−179.9 (4)
C2—C1—C6—C5	−1.7 (5)	C12—C11—C15—N3	−1.8 (7)
C2—C1—C7—N1	40.2 (4)	C11—C12—C13—C14	0.8 (7)
C7—C1—C6—C5	177.3 (3)	C12—C13—C14—N3	−0.7 (8)
C2—C1—C7—S1	−76.2 (3)

Symmetry codes: (i) −x+y−1, −x+1, z; (ii) y−1, −x+y, −z+1; (iii) −y+4/3, x−y+5/3, z+2/3; (iv) −x+y−1/3, −x+4/3, z+1/3; (v) x−y+1, x+1, −z+1; (vi) −y+4/3, x−y+5/3, z−1/3; (vii) −x+y−1/3, −x+4/3, z−2/3; (viii) −x+2/3, −y+7/3, −z+1/3; (ix) −y+1, x−y+2, z.

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^vi	0.85 (3)	2.07 (3)	2.914 (4)	172 (4)
C3—H3···O2^vi	0.93	2.43	3.237 (5)	146
C15—H15···N2	0.93	2.54	2.864 (5)	101
C15—H15···O1^vi	0.93	2.50	3.399 (5)	162
C14—H14···Cg3^x	0.93	2.79	3.692 (4)	164

Symmetry codes: (vi) −y+4/3, x−y+5/3, z−1/3; (x) x+1, y, z+2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrN₃O₂S
M_r	378.25
Crystal system, space group	Trigonal, R3
Temperature (K)	296
a, c (Å)	24.9588 (9), 12.8013 (5)
V (Å³)	6906.1 (4)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	2.82
Crystal size (mm)	0.28 × 0.23 × 0.19

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.505, 0.616
No. of measured, independent and observed [I > 2σ(I)] reflections	13554, 3174, 1963
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.085, 0.95
No. of reflections	3174
No. of parameters	202
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.35

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

Cg3 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.85 (3)	2.07 (3)	2.914 (4)	172 (4)
C3—H3···O2ⁱ	0.93	2.43	3.237 (5)	146
C15—H15···N2	0.93	2.54	2.864 (5)	101
C15—H15···O1ⁱ	0.93	2.50	3.399 (5)	162
C14—H14···Cg3ⁱⁱ	0.93	2.79	3.692 (4)	164

Symmetry codes: (i) −y+4/3, x−y+5/3, z−1/3; (ii) x+1, y, z+2.

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). HD and SO acknowledge the Scientific Research Projects Coordination Unit of Istanbul University (Project number T-3691).

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Volume 66| Part 7| July 2010| Pages o1691-o1692

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