3-Bromo-2-[4-(methyl­sulfan­yl)phen­yl]-5,6,7,8-tetra­hydro-1,3-benzo­thia­zolo[3,2-a]imidazole

Bunev, A.S.; Sukhonosova, E.V.; Statsyuk, V.E.; Ostapenko, G.I.; Khrustalev, V.N.

doi:10.1107/S1600536814008976

organic compounds

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ISSN: 2056-9890

Volume 70| Part 5| May 2014| Pages o596-o597

doi:10.1107/S1600536814008976

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3-Bromo-2-[4-(methylsulfanyl)phenyl]-5,6,7,8-tetrahydro-1,3-benzothiazolo[3,2-a]imidazole

Alexander S. Bunev,^a ^* Elena V. Sukhonosova,^b Vladimir E. Statsyuk,^a Gennady I. Ostapenko ^a and Victor N. Khrustalev ^c

^aDepartment of Chemistry and Chemical Technology, Togliatti State University, 14 Belorusskaya St, Togliatti 445667, Russian Federation, ^bDepartment of Organic, Bioorganic and Medicinal Chemistry, Samara State University, 1 Akademician Pavlov St, Samara 443011, Russian Federation, and ^cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, B-334, Moscow 119991, Russian Federation
^*Correspondence e-mail: a.s.bunev@gmail.com

(Received 31 March 2014; accepted 20 April 2014; online 26 April 2014)

In the title molecule, C₁₆H₁₅BrN₂S₂, the central imidazo[2,1-b]thiazole fragment is almost planar (r.m.s. deviation = 0.012 Å), and the fused 5,6,7,8-tetrahydrobenzene ring adopts an unsymmetrical half-chair conformation. The dihedral angle between the imidazo[2,1-b]thiazole and benzene planes is 18.25 (4)°. The terminal methylsulfanyl substituent lies practically within the benzene plane [the dihedral angle between the corresponding planes is 7.20 (10)°] and is turned toward the C—Br bond. In the crystal, molecules form infinite chains along [100] via secondary Br⋯N interactions [3.1861 (16) Å]. The chains are arranged at van der Waals distances.

CCDC reference: 998505

Related literature

For applications of imidazo[2,1-b][1,3]benzothiazoles, see: Ager et al. (1988 ); Sanfilippo et al. (1988 ); Barchéchath et al. (2005 ); Andreani et al. (2008 ); Chao et al. (2009 ); Kumbhare et al. (2011 ); Chandak et al. (2013 ). For the crystal structures of related compounds, see: Landreau et al. (2002 ); Adib et al. (2008 ); Fun, Asik et al. (2011 ); Fun, Hemamalini et al. (2011 ); Ghabbour et al. (2012 ); Bunev et al. (2013 , 2014 ).

Experimental

Crystal data

C₁₆H₁₅BrN₂S₂
M_r = 379.34
Triclinic, $[P \overline 1]$
a = 7.3132 (3) Å
b = 7.5663 (3) Å
c = 14.4543 (7) Å
α = 95.033 (1)°
β = 97.188 (1)°
γ = 101.938 (1)°
V = 771.03 (6) Å³
Z = 2
Mo Kα radiation
μ = 2.93 mm⁻¹
T = 120 K
0.15 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.668, T_max = 0.758
10352 measured reflections
4508 independent reflections
3927 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.073
S = 1.05
4508 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 998505

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814008976/rk2426sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814008976/rk2426Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814008976/rk2426Isup3.cml

checkCIF report

Comment top

Imidazo[2,1–b][1,3]benzothiazole are of great interest due to their biological properties. These compounds and their derivatives demonstrate the antitumor (Andreani et al., 2008), antiallergic (Ager et al., 1988), anesthetic (Sanfilippo et al., 1988) and anti–cancer (Kumbhare et al., 2011) activities as well as the inhibition activity of apoptosis in testiculargerm cells (Chandak et al., 2013), lymphocytes (Barchéchath et al., 2005), and FMS–like tyrosine kinase–3 (FLT3) (Chao et al., 2009).

In this work, a new halogensubstituted 5,6,7,8–tetrahydrobenzo[d]imidazo[2,1–b]thiazole, C₁₆H₁₅BrN₂S₂, I, was prepared by the reaction of 5,6,7,8–tetrahydrobenzo[d]imidazo[2,1–b]thiazole with bromine at room temperature (Fig. 1), and its structure was unambiguously established by the X–ray diffraction study (Fig. 2).

In the title molecule (I) the central imidazo[2,1–b]thiazole fragment is almost planar (r.m.s. deviation = 0.012 Å), and the fused 5,6,7,8-tetrahydrobenzene ring adopts an unsymmetrical half–chair conformation (the C6 and C7 carbon atoms are out of the plane passed through the other atoms of the ring by -0.246 (2) and 0.508 (2) Å, respectively). The bond lengths and angles within the molecule of I are in a good agreement with those found in the related compounds (Landreau et al., 2002; Adib et al., 2008; Fun, Asik et al., 2011; Fun, Hemamalini et al., 2011; Ghabbour et al., 2012; Bunev et al., 2013, 2014). The dihedral angle between the imidazo[2,1–b]thiazole and benzene planes is 18.25 (4)°. The terminal methylthio substituent lies practically within the benzene plane (the dihedral angle between the corresponding planes is 7.20 (10)°) and is turned toward the C—Br bond.

In the crystal, the molecules of I form infinite chains along [100] by intermolecular secondary Br1···N1ⁱ interactions (3.1861 (16) Å) (Fig. 3). The chains are arranged at van der Waals distances. Symmetry code: (i) 1 + x, y, z.

Related literature top

For applications of imidazo[2,1-b][1,3]benzothiazoles, see: Ager et al. (1988); Sanfilippo et al. (1988); Barchéchath et al. (2005); Andreani et al. (2008); Chao et al. (2009); Kumbhare et al. (2011); Chandak et al. (2013). For the crystal structures of related compounds, see: Landreau et al. (2002); Adib et al. (2008); Fun, Asik et al. (2011); Fun, Hemamalini et al. (2011); Ghabbour et al. (2012); Bunev et al. (2013, 2014).

Experimental top

A solution of bromine (139 µL, 430.4 mg, 2.69 mmol) in dry CHCl₃ (10 mL) was added to a solutions 2–(4–(methylthio)phenyl)–5,6,7,8–tetrahydrobenzo[d]imidazo[2,1–b]thiazole (808.3 mg, 2.69 mmol) in dry CHCl₃ (30 mL). The reaction mixture was stirred at room temperature for 3 h. the solvent was evaporated from the reaction mixture on rotavapor. The crude product was diluted with 5% solution Na₂CO₃ in water (25 mL). The precipitate was filtered and crystallized from DMF. Yield is 75%. The single–crystal of the product I was obtained by slow crystallization from DMF. M.p. = 439–441 K. IR (KBr), ν/cm^-1: 3131, 3073, 1580, 1523, 1501, 1337, 1144, 815, 714. ¹H NMR (600 MHz, DMSO–d₆, 304 K): 7.63 (d, 2H, J = 8.9), 7.54 (d, 2H, J = 8.9), 3.39–3.33 (m, 2H), 3.02–2.96 (m, 2H), 2.45 (s, 3H), 1.91–1.81 (m, 4H). Anal. Calcd for C₁₆H₁₅BrN₂S: C, 50.66; H, 3.99. Found: C, 50.57; H, 4.08.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

	Fig. 1. The synthesis of 3-bromo-2-[4-(methylsulfanyl)phenyl]-5,6,7,8-tetrahydro-1,3-benzothiazolo[3,2-a]imidazole.
	Fig. 2. Molecular structure of I. Displacement ellipsoids are presented at the 50% probability level. H atoms are depicted as small spheres of arbitrary radius.
	Fig. 3. A portion of the crystal structure of I demonstrating the chains along [100]. The intermolecular secondary Br···N interactions are depicted by dashed lines.

3-Bromo-2-[4-(methylsulfanyl)phenyl]-5,6,7,8-tetrahydro-1,3-benzothiazolo[3,2-a]imidazole top

Crystal data top

C₁₆H₁₅BrN₂S₂	Z = 2
M_r = 379.34	F(000) = 384
Triclinic, P1	D_x = 1.634 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3132 (3) Å	Cell parameters from 4428 reflections
b = 7.5663 (3) Å	θ = 2.8–32.3°
c = 14.4543 (7) Å	µ = 2.93 mm⁻¹
α = 95.033 (1)°	T = 120 K
β = 97.188 (1)°	Prism, colourless
γ = 101.938 (1)°	0.15 × 0.10 × 0.10 mm
V = 771.03 (6) Å³

Data collection top

Bruker APEXII CCD diffractometer	4508 independent reflections
Radiation source: fine-focus sealed tube	3927 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
T_min = 0.668, T_max = 0.758	k = −10→10
10352 measured reflections	l = −20→20

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0377P)² + 0.1351P] where P = (F_o² + 2F_c²)/3
4508 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₅BrN₂S₂	γ = 101.938 (1)°
M_r = 379.34	V = 771.03 (6) Å³
Triclinic, P1	Z = 2
a = 7.3132 (3) Å	Mo Kα radiation
b = 7.5663 (3) Å	µ = 2.93 mm⁻¹
c = 14.4543 (7) Å	T = 120 K
α = 95.033 (1)°	0.15 × 0.10 × 0.10 mm
β = 97.188 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4508 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	3927 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.758	R_int = 0.025
10352 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.05	Δρ_max = 0.67 e Å⁻³
4508 reflections	Δρ_min = −0.32 e Å⁻³
191 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
Br1	0.52846 (2)	0.33371 (2)	0.103656 (13)	0.01782 (6)
S1	0.31673 (8)	0.75383 (8)	0.55165 (4)	0.02712 (12)
N1	−0.0318 (2)	0.3490 (2)	0.10823 (11)	0.0169 (3)
C2	0.1565 (3)	0.3866 (2)	0.15151 (13)	0.0150 (3)
C3	0.2697 (2)	0.3284 (2)	0.09002 (13)	0.0146 (3)
N4	0.1494 (2)	0.2541 (2)	0.00724 (10)	0.0136 (3)
C4A	0.1551 (3)	0.1754 (2)	−0.08424 (13)	0.0147 (3)
C5	0.3302 (3)	0.1399 (2)	−0.11797 (13)	0.0159 (3)
H5A	0.3921	0.0696	−0.0739	0.019*
H5B	0.4195	0.2568	−0.1199	0.019*
C6	0.2819 (3)	0.0326 (3)	−0.21646 (14)	0.0194 (4)
H6A	0.3978	0.0462	−0.2464	0.023*
H6B	0.2372	−0.0981	−0.2106	0.023*
C7	0.1308 (3)	0.0964 (3)	−0.27918 (13)	0.0208 (4)
H7A	0.1110	0.0295	−0.3429	0.025*
H7B	0.1735	0.2276	−0.2844	0.025*
C8	−0.0560 (3)	0.0635 (3)	−0.23845 (13)	0.0186 (4)
H8A	−0.1458	0.1253	−0.2726	0.022*
H8B	−0.1133	−0.0684	−0.2457	0.022*
C8A	−0.0175 (3)	0.1366 (2)	−0.13656 (13)	0.0154 (3)
S9	−0.19453 (6)	0.18940 (6)	−0.07481 (3)	0.01700 (10)
C9A	−0.0272 (2)	0.2722 (2)	0.02379 (13)	0.0153 (3)
C10	0.2059 (3)	0.4782 (2)	0.24789 (13)	0.0164 (3)
C11	0.0607 (3)	0.4836 (3)	0.30255 (14)	0.0191 (4)
H11	−0.0658	0.4267	0.2767	0.023*
C12	0.0991 (3)	0.5705 (3)	0.39362 (14)	0.0204 (4)
H12	−0.0014	0.5733	0.4291	0.024*
C13	0.2850 (3)	0.6542 (3)	0.43388 (13)	0.0199 (4)
C14	0.4292 (3)	0.6527 (3)	0.37994 (14)	0.0232 (4)
H14	0.5554	0.7108	0.4058	0.028*
C15	0.3898 (3)	0.5664 (3)	0.28802 (14)	0.0217 (4)
H15	0.4900	0.5676	0.2520	0.026*
C16	0.5684 (3)	0.8198 (3)	0.58283 (16)	0.0302 (5)
H16A	0.6001	0.8615	0.6502	0.045*
H16B	0.6187	0.9185	0.5472	0.045*
H16C	0.6242	0.7154	0.5682	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01313 (9)	0.02030 (10)	0.01932 (10)	0.00599 (7)	−0.00109 (6)	−0.00219 (7)
S1	0.0271 (3)	0.0327 (3)	0.0173 (2)	0.0007 (2)	0.0029 (2)	−0.0057 (2)
N1	0.0157 (7)	0.0163 (7)	0.0187 (8)	0.0026 (6)	0.0042 (6)	0.0015 (6)
C2	0.0154 (8)	0.0140 (8)	0.0158 (8)	0.0029 (7)	0.0033 (7)	0.0023 (6)
C3	0.0134 (8)	0.0155 (8)	0.0154 (8)	0.0051 (7)	0.0010 (6)	0.0008 (6)
N4	0.0109 (7)	0.0153 (7)	0.0145 (7)	0.0034 (6)	0.0011 (5)	0.0010 (6)
C4A	0.0145 (8)	0.0121 (8)	0.0175 (9)	0.0030 (6)	0.0023 (7)	0.0016 (6)
C5	0.0140 (8)	0.0160 (8)	0.0186 (9)	0.0050 (7)	0.0036 (7)	0.0004 (7)
C6	0.0195 (9)	0.0217 (9)	0.0179 (9)	0.0083 (8)	0.0030 (7)	−0.0010 (7)
C7	0.0221 (9)	0.0247 (10)	0.0159 (9)	0.0070 (8)	0.0025 (7)	−0.0004 (7)
C8	0.0178 (9)	0.0193 (9)	0.0167 (9)	0.0036 (7)	−0.0016 (7)	−0.0013 (7)
C8A	0.0136 (8)	0.0140 (8)	0.0182 (8)	0.0025 (7)	0.0028 (7)	0.0007 (6)
S9	0.01080 (19)	0.0210 (2)	0.0186 (2)	0.00355 (17)	0.00092 (16)	0.00057 (17)
C9A	0.0119 (8)	0.0160 (8)	0.0186 (8)	0.0030 (7)	0.0033 (7)	0.0031 (7)
C10	0.0192 (9)	0.0129 (8)	0.0167 (8)	0.0027 (7)	0.0028 (7)	0.0010 (6)
C11	0.0176 (9)	0.0174 (9)	0.0208 (9)	0.0017 (7)	0.0021 (7)	0.0001 (7)
C12	0.0211 (9)	0.0208 (9)	0.0193 (9)	0.0037 (8)	0.0051 (7)	0.0010 (7)
C13	0.0252 (10)	0.0187 (9)	0.0145 (8)	0.0037 (8)	0.0019 (7)	−0.0011 (7)
C14	0.0196 (9)	0.0252 (10)	0.0208 (10)	−0.0006 (8)	0.0014 (7)	−0.0028 (8)
C15	0.0205 (9)	0.0235 (10)	0.0194 (9)	0.0009 (8)	0.0063 (7)	−0.0012 (8)
C16	0.0286 (11)	0.0311 (12)	0.0249 (11)	−0.0003 (9)	−0.0030 (9)	−0.0030 (9)

Geometric parameters (Å, º) top

Br1—C3	1.8693 (18)	C7—H7B	0.9900
S1—C13	1.7673 (19)	C8—C8A	1.498 (3)
S1—C16	1.793 (2)	C8—H8A	0.9900
N1—C9A	1.312 (2)	C8—H8B	0.9900
N1—C2	1.400 (2)	C8A—S9	1.7529 (19)
C2—C3	1.391 (2)	S9—C9A	1.7354 (19)
C2—C10	1.467 (3)	C10—C15	1.399 (3)
C3—N4	1.391 (2)	C10—C11	1.405 (3)
N4—C9A	1.374 (2)	C11—C12	1.387 (3)
N4—C4A	1.411 (2)	C11—H11	0.9500
C4A—C8A	1.349 (2)	C12—C13	1.403 (3)
C4A—C5	1.492 (2)	C12—H12	0.9500
C5—C6	1.537 (3)	C13—C14	1.389 (3)
C5—H5A	0.9900	C14—C15	1.396 (3)
C5—H5B	0.9900	C14—H14	0.9500
C6—C7	1.524 (3)	C15—H15	0.9500
C6—H6A	0.9900	C16—H16A	0.9800
C6—H6B	0.9900	C16—H16B	0.9800
C7—C8	1.537 (3)	C16—H16C	0.9800
C7—H7A	0.9900

C13—S1—C16	103.71 (10)	C8A—C8—H8B	109.9
C9A—N1—C2	104.13 (15)	C7—C8—H8B	109.9
C3—C2—N1	110.13 (16)	H8A—C8—H8B	108.3
C3—C2—C10	130.54 (17)	C4A—C8A—C8	124.20 (17)
N1—C2—C10	119.33 (16)	C4A—C8A—S9	113.31 (14)
C2—C3—N4	106.03 (15)	C8—C8A—S9	122.44 (13)
C2—C3—Br1	131.99 (14)	C9A—S9—C8A	89.99 (9)
N4—C3—Br1	121.98 (13)	N1—C9A—N4	114.32 (16)
C9A—N4—C3	105.38 (15)	N1—C9A—S9	134.58 (14)
C9A—N4—C4A	114.32 (15)	N4—C9A—S9	111.08 (13)
C3—N4—C4A	140.26 (16)	C15—C10—C11	117.62 (17)
C8A—C4A—N4	111.27 (16)	C15—C10—C2	123.61 (17)
C8A—C4A—C5	124.77 (17)	C11—C10—C2	118.73 (17)
N4—C4A—C5	123.97 (16)	C12—C11—C10	121.15 (18)
C4A—C5—C6	110.25 (15)	C12—C11—H11	119.4
C4A—C5—H5A	109.6	C10—C11—H11	119.4
C6—C5—H5A	109.6	C11—C12—C13	120.61 (18)
C4A—C5—H5B	109.6	C11—C12—H12	119.7
C6—C5—H5B	109.6	C13—C12—H12	119.7
H5A—C5—H5B	108.1	C14—C13—C12	118.75 (18)
C7—C6—C5	112.55 (15)	C14—C13—S1	124.86 (16)
C7—C6—H6A	109.1	C12—C13—S1	116.38 (15)
C5—C6—H6A	109.1	C13—C14—C15	120.45 (19)
C7—C6—H6B	109.1	C13—C14—H14	119.8
C5—C6—H6B	109.1	C15—C14—H14	119.8
H6A—C6—H6B	107.8	C14—C15—C10	121.38 (18)
C6—C7—C8	110.44 (16)	C14—C15—H15	119.3
C6—C7—H7A	109.6	C10—C15—H15	119.3
C8—C7—H7A	109.6	S1—C16—H16A	109.5
C6—C7—H7B	109.6	S1—C16—H16B	109.5
C8—C7—H7B	109.6	H16A—C16—H16B	109.5
H7A—C7—H7B	108.1	S1—C16—H16C	109.5
C8A—C8—C7	109.02 (15)	H16A—C16—H16C	109.5
C8A—C8—H8A	109.9	H16B—C16—H16C	109.5
C7—C8—H8A	109.9

C9A—N1—C2—C3	−0.4 (2)	C8—C8A—S9—C9A	−175.86 (16)
C9A—N1—C2—C10	178.60 (16)	C2—N1—C9A—N4	0.5 (2)
N1—C2—C3—N4	0.2 (2)	C2—N1—C9A—S9	−178.31 (16)
C10—C2—C3—N4	−178.66 (17)	C3—N4—C9A—N1	−0.4 (2)
N1—C2—C3—Br1	−178.84 (14)	C4A—N4—C9A—N1	−178.63 (15)
C10—C2—C3—Br1	2.3 (3)	C3—N4—C9A—S9	178.71 (12)
C2—C3—N4—C9A	0.07 (19)	C4A—N4—C9A—S9	0.45 (19)
Br1—C3—N4—C9A	179.24 (12)	C8A—S9—C9A—N1	177.7 (2)
C2—C3—N4—C4A	177.6 (2)	C8A—S9—C9A—N4	−1.11 (14)
Br1—C3—N4—C4A	−3.2 (3)	C3—C2—C10—C15	17.2 (3)
C9A—N4—C4A—C8A	0.7 (2)	N1—C2—C10—C15	−161.53 (18)
C3—N4—C4A—C8A	−176.6 (2)	C3—C2—C10—C11	−164.91 (19)
C9A—N4—C4A—C5	−179.12 (16)	N1—C2—C10—C11	16.3 (3)
C3—N4—C4A—C5	3.5 (3)	C15—C10—C11—C12	−1.1 (3)
C8A—C4A—C5—C6	−6.7 (3)	C2—C10—C11—C12	−179.12 (17)
N4—C4A—C5—C6	173.18 (16)	C10—C11—C12—C13	−0.5 (3)
C4A—C5—C6—C7	39.6 (2)	C11—C12—C13—C14	1.7 (3)
C5—C6—C7—C8	−63.1 (2)	C11—C12—C13—S1	−177.96 (15)
C6—C7—C8—C8A	49.1 (2)	C16—S1—C13—C14	−6.6 (2)
N4—C4A—C8A—C8	175.79 (16)	C16—S1—C13—C12	173.04 (16)
C5—C4A—C8A—C8	−4.3 (3)	C12—C13—C14—C15	−1.2 (3)
N4—C4A—C8A—S9	−1.6 (2)	S1—C13—C14—C15	178.47 (16)
C5—C4A—C8A—S9	178.26 (14)	C13—C14—C15—C10	−0.5 (3)
C7—C8—C8A—C4A	−17.4 (3)	C11—C10—C15—C14	1.7 (3)
C7—C8—C8A—S9	159.79 (14)	C2—C10—C15—C14	179.55 (18)
C4A—C8A—S9—C9A	1.59 (15)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅BrN₂S₂
M_r	379.34
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	7.3132 (3), 7.5663 (3), 14.4543 (7)
α, β, γ (°)	95.033 (1), 97.188 (1), 101.938 (1)
V (Å³)	771.03 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.93
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.668, 0.758
No. of measured, independent and observed [I > 2σ(I)] reflections	10352, 4508, 3927
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.073, 1.05
No. of reflections	4508
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.32

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the Ministry of Education and Science of the Russian Federation (State program No. 426).

References

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