2-(5-Bromo­thio­phen-2-yl)-5-[5-(10-ethyl­phenothia­zin-3-yl)thio­phen-2-yl]-1,3,4-oxadiazole

Pan, Y.-Z.; Wang, Y.-G.; Liu, J.-H.; Sun, L.-C.

doi:10.1107/S160053681201361X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1383-o1384

doi:10.1107/S160053681201361X

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2-(5-Bromothiophen-2-yl)-5-[5-(10-ethylphenothiazin-3-yl)thiophen-2-yl]-1,3,4-oxadiazole

Yu-Zhen Pan,^a You-Gui Wang,^a Jian-Hui Liu ^b ^* and Li-Cheng Sun ^b,^c ^*

^aCollege of Chemistry, Dalian University of Technology, 116024 Dalian, Liaoning, People's Republic of China, ^bState Key Laboratory of Fine Chemicals, DUT-KTH Joint Education and Research Center on Molecular Devices, Dalian University of Technology, 116024 Dalian, Liaoning, People's Republic of China, and ^cDepartment of Chemistry, School of Chemical Science and Engineering, KTH Royal Institute of Technology, Stockholm 10044, Sweden
^*Correspondence e-mail: liujh@dlut.edu.cn, lichengs@kth.se

(Received 19 March 2012; accepted 29 March 2012; online 13 April 2012)

The molecule of the title compound, C₂₄H₁₆BrN₃OS₃, contains three approximately planar fragments, viz. an oxadiazole ring plus two adjacent thiophene groups, and two phenothiazine benzene rings, with largest deviations from the least-squares planes of 0.051 (3), 0.019 (4) and 0.014 (3) Å, respectively. The phenothiazine unit adopts a butterfly conformation, with a dihedral angle of 38.06 (15)° between the terminal benzene rings. The dihedral angle between the 2,5-bis(thiophen-2-yl)oxadiazole unit and the attached benzene ring is 15.35 (11)°. In the crystal, molecules form stacks along the b-axis direction; neighboring molecules within the stack are related by inversion centers, with shortest intercentroid separations of 3.741 (2) and 3.767 (2) Å.

Related literature

For electro-optical properties of phenothiazine derivatives, see: Lai et al. (2001 , 2003 ); Han et al. (2008 ); Meng et al. (2010 ); Zhang et al. (2005 ); Park et al. (2011 ); Kim et al. (2011 ); Hagfeldt et al. (2010 ); Wu et al. (2010 ). For related structures, see: Chu & Van der Helm (1975 ); Hdii et al. (1998 ); Li et al. (2009a ,b ); Yu et al. (2011 ); Pan et al. (2012 ).

Experimental

Crystal data

C₂₄H₁₆BrN₃OS₃
M_r = 538.49
Triclinic, $[P \overline 1]$
a = 7.4300 (5) Å
b = 7.6019 (5) Å
c = 22.1933 (14) Å
α = 89.315 (4)°
β = 89.170 (4)°
γ = 64.891 (4)°
V = 1134.93 (13) Å³
Z = 2
Mo Kα radiation
μ = 2.11 mm⁻¹
T = 296 K
0.10 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.812, T_max = 0.860
11444 measured reflections
3972 independent reflections
3138 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.136
S = 1.06
3972 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2004 ) and SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681201361X/yk2050sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201361X/yk2050Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201361X/yk2050Isup3.cml

checkCIF report

Comment top

The derivatives of phenothiazine have attracted much interest since they can serve as photoactive and electroactive materials in many fields, such as electrogenerated chemiluminescence (Lai et al., 2001, 2003), environment sensitive fluorophores (Han et al., 2008; Meng et al., 2010), organic light-emitting diodes (Zhang et al., 2005; Park et al., 2011) and solar cells (Hagfeldt et al., 2010; Kim et al., 2011; Wu et al., 2010). As part of our studies on these materials, here we report the crystal structure of the title compound, C₂₄H₁₆BrN₃OS₃.

In the molecule of the title compound (Fig. 1), two benzene rings of the phenothiazine group display a noncoplanar butterfly conformation with a dihedral angle of 38.06 (15)°. Both thiophene rings, oxadiazole group and benzene ring with C9 atom of phenthiazine lie almost in the same plane. In the crystal, there are C—H···N contacts and π-π interactions between neighbouring molecules.

Related literature top

For electro-optical properties of phenothiazine derivatives, see: Lai et al. (2001, 2003); Han et al. (2008); Meng et al. (2010); Zhang et al. (2005); Park et al. (2011); Kim et al. (2011); Hagfeldt et al. (2010); Wu et al. (2010). For related structures, see: Chu & Van der Helm (1975); Hdii et al. (1998); Li et al. (2009a,b); Yu et al. (2011); Pan et al. (2012).

Experimental top

3-dihydroxyboryl-10-ethylphenothiazine (320 mg, 1.2 mmol), 2,5-bis(5-bromo-2-thiophen-2-yl)-1,3,4-oxadiazole (350 mg, 0.9 mmol) and Pd(PPh₃)₄ (21 mg, 0.02 mmol) were dissolved in 20 ml THF under nitrogen atmosphere, then aqueous solution of Na₂CO₃ (2.0 M, 6 mL) was added to reaction mixture. The mixture was stirred at 80°C for 24 hrs, then it was poured into water and extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate. After removal of the solvent, the crude product was purified by chromatography on a silica gel column using dichloromethane-ethyl acetate (v/v = 150:1) as eluent and isolated as a yellow powder. Yield: 145 mg (30%). The yellow single crystals suitable for X-ray analysis were obtained after several days by slow evaporation of a mixture solution in dichloromethane and petroleum ether.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2004) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Fig. 1. Structure of the title compound with atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level.

2-(5-Bromothiophen-2-yl)-5-[5-(10-ethylphenothiazin-3-yl)thiophen-2-yl]- 1,3,4-oxadiazole top

Crystal data top

C₂₄H₁₆BrN₃OS₃	Z = 2
M_r = 538.49	F(000) = 544
Triclinic, P1	D_x = 1.576 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4300 (5) Å	Cell parameters from 4410 reflections
b = 7.6019 (5) Å	θ = 2.8–25.6°
c = 22.1933 (14) Å	µ = 2.11 mm⁻¹
α = 89.315 (4)°	T = 296 K
β = 89.170 (4)°	Block, yellow
γ = 64.891 (4)°	0.10 × 0.08 × 0.07 mm
V = 1134.93 (13) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3972 independent reflections
Radiation source: fine-focus sealed tube	3138 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
phi and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.812, T_max = 0.860	k = −8→9
11444 measured reflections	l = −26→26

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0813P)² + 0.0555P] where P = (F_o² + 2F_c²)/3
3972 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₂₄H₁₆BrN₃OS₃	γ = 64.891 (4)°
M_r = 538.49	V = 1134.93 (13) Å³
Triclinic, P1	Z = 2
a = 7.4300 (5) Å	Mo Kα radiation
b = 7.6019 (5) Å	µ = 2.11 mm⁻¹
c = 22.1933 (14) Å	T = 296 K
α = 89.315 (4)°	0.10 × 0.08 × 0.07 mm
β = 89.170 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3972 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3138 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.860	R_int = 0.052
11444 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.06	Δρ_max = 0.47 e Å⁻³
3972 reflections	Δρ_min = −0.62 e Å⁻³
290 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 > σ(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	−0.64760 (7)	0.55973 (6)	0.18906 (2)	0.0835 (2)
C1	0.3622 (6)	0.2273 (5)	0.96143 (15)	0.0594 (9)
H1	0.2281	0.2762	0.9718	0.071*
C2	0.4887 (7)	0.2710 (5)	0.99607 (17)	0.0673 (10)
H2	0.4416	0.3463	1.0304	0.081*
C3	0.6867 (7)	0.2023 (5)	0.97957 (17)	0.0682 (11)
H3	0.7731	0.2313	1.0031	0.082*
C4	0.7577 (5)	0.0905 (5)	0.92832 (16)	0.0587 (9)
H4	0.8904	0.0489	0.9170	0.070*
C5	0.6325 (5)	0.0397 (4)	0.89353 (14)	0.0456 (7)
C6	0.4320 (5)	0.1113 (4)	0.91116 (13)	0.0465 (7)
C7	0.9127 (5)	−0.2003 (6)	0.83409 (18)	0.0666 (10)
H7A	0.9822	−0.1174	0.8320	0.080*
H7B	0.9341	−0.2683	0.7961	0.080*
C8	0.9994 (6)	−0.3473 (6)	0.8843 (2)	0.0839 (13)
H8A	0.9828	−0.2808	0.9219	0.126*
H8B	1.1383	−0.4238	0.8765	0.126*
H8C	0.9320	−0.4307	0.8863	0.126*
C9	0.5786 (5)	−0.0232 (4)	0.79035 (14)	0.0437 (7)
C10	0.6538 (5)	−0.0294 (5)	0.73245 (15)	0.0522 (8)
H10	0.7888	−0.0638	0.7269	0.063*
C11	0.5316 (5)	0.0147 (4)	0.68302 (15)	0.0501 (8)
H11	0.5870	0.0038	0.6446	0.060*
C12	0.3283 (5)	0.0748 (4)	0.68915 (13)	0.0450 (7)
C13	0.2503 (5)	0.0895 (4)	0.74764 (14)	0.0465 (7)
H13	0.1138	0.1335	0.7532	0.056*
C14	0.3721 (5)	0.0401 (4)	0.79706 (14)	0.0452 (7)
C15	0.1960 (5)	0.1204 (4)	0.63696 (14)	0.0468 (7)
C16	0.0059 (5)	0.1390 (4)	0.63392 (15)	0.0508 (8)
H16	−0.0620	0.1199	0.6671	0.061*
C17	−0.0786 (5)	0.1891 (4)	0.57703 (14)	0.0516 (8)
H17	−0.2075	0.2072	0.5685	0.062*
C18	0.0480 (5)	0.2087 (4)	0.53520 (15)	0.0488 (7)
C19	0.0111 (5)	0.2606 (4)	0.47247 (14)	0.0469 (7)
C20	−0.1542 (5)	0.3449 (4)	0.39177 (14)	0.0448 (7)
C21	−0.3225 (5)	0.3959 (4)	0.35297 (14)	0.0449 (7)
C22	−0.5041 (5)	0.4019 (4)	0.36531 (16)	0.0546 (8)
H22	−0.5420	0.3753	0.4032	0.065*
C23	−0.6299 (5)	0.4525 (4)	0.31502 (17)	0.0570 (8)
H23	−0.7589	0.4620	0.3157	0.068*
C24	−0.5401 (5)	0.4854 (4)	0.26594 (14)	0.0515 (8)
N1	0.6991 (4)	−0.0788 (4)	0.84232 (12)	0.0492 (6)
N2	0.1313 (4)	0.2746 (4)	0.43185 (12)	0.0563 (7)
N3	0.0218 (4)	0.3301 (4)	0.37835 (12)	0.0554 (7)
O1	−0.1732 (3)	0.3035 (3)	0.45107 (9)	0.0466 (5)
S1	0.27273 (13)	0.04182 (14)	0.86988 (4)	0.0583 (3)
S2	0.27462 (13)	0.16405 (12)	0.56662 (4)	0.0537 (2)
S3	−0.30112 (13)	0.45375 (12)	0.27857 (4)	0.0536 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1064 (4)	0.0847 (3)	0.0675 (3)	−0.0479 (3)	−0.0321 (3)	0.0175 (2)
C1	0.070 (2)	0.0534 (17)	0.0436 (19)	−0.0159 (16)	0.0046 (17)	0.0046 (15)
C2	0.101 (3)	0.0543 (18)	0.046 (2)	−0.032 (2)	−0.005 (2)	−0.0026 (15)
C3	0.102 (3)	0.066 (2)	0.052 (2)	−0.051 (2)	−0.014 (2)	0.0023 (17)
C4	0.065 (2)	0.0672 (19)	0.056 (2)	−0.0394 (17)	−0.0077 (17)	0.0088 (17)
C5	0.0504 (18)	0.0507 (15)	0.0412 (17)	−0.0270 (14)	−0.0026 (14)	0.0072 (13)
C6	0.0567 (19)	0.0486 (15)	0.0362 (17)	−0.0243 (14)	−0.0032 (14)	0.0072 (13)
C7	0.047 (2)	0.078 (2)	0.068 (3)	−0.0199 (17)	0.0001 (18)	−0.0067 (19)
C8	0.071 (3)	0.077 (2)	0.083 (3)	−0.011 (2)	−0.022 (2)	0.000 (2)
C9	0.0466 (17)	0.0477 (15)	0.0412 (17)	−0.0242 (13)	0.0027 (14)	−0.0011 (13)
C10	0.0461 (18)	0.0637 (18)	0.050 (2)	−0.0267 (15)	0.0068 (15)	−0.0067 (15)
C11	0.054 (2)	0.0569 (17)	0.0405 (18)	−0.0245 (15)	0.0095 (15)	−0.0066 (14)
C12	0.0524 (19)	0.0425 (14)	0.0420 (18)	−0.0219 (13)	0.0056 (14)	−0.0029 (13)
C13	0.0435 (17)	0.0532 (16)	0.0441 (18)	−0.0219 (13)	0.0037 (14)	−0.0011 (13)
C14	0.0495 (18)	0.0504 (15)	0.0415 (17)	−0.0267 (14)	0.0020 (14)	−0.0004 (13)
C15	0.059 (2)	0.0415 (14)	0.0412 (17)	−0.0224 (14)	0.0048 (15)	−0.0023 (12)
C16	0.056 (2)	0.0576 (17)	0.0407 (18)	−0.0262 (15)	0.0045 (15)	0.0028 (14)
C17	0.0516 (19)	0.0571 (17)	0.0462 (19)	−0.0231 (15)	0.0030 (15)	−0.0027 (14)
C18	0.0534 (19)	0.0445 (14)	0.0458 (18)	−0.0184 (13)	0.0029 (15)	−0.0016 (13)
C19	0.0511 (19)	0.0452 (15)	0.0428 (18)	−0.0189 (13)	0.0016 (15)	−0.0026 (13)
C20	0.0490 (18)	0.0435 (14)	0.0403 (17)	−0.0183 (13)	0.0085 (14)	−0.0030 (12)
C21	0.0519 (18)	0.0408 (14)	0.0429 (17)	−0.0208 (13)	0.0075 (14)	−0.0007 (12)
C22	0.057 (2)	0.0539 (17)	0.052 (2)	−0.0230 (15)	0.0095 (17)	0.0028 (15)
C23	0.0512 (19)	0.0544 (17)	0.066 (2)	−0.0227 (15)	0.0007 (17)	0.0030 (16)
C24	0.063 (2)	0.0463 (15)	0.0466 (19)	−0.0247 (15)	−0.0021 (16)	0.0022 (14)
N1	0.0415 (14)	0.0610 (14)	0.0447 (16)	−0.0214 (12)	−0.0002 (12)	−0.0031 (12)
N2	0.0556 (17)	0.0717 (16)	0.0431 (16)	−0.0287 (14)	0.0030 (13)	0.0036 (13)
N3	0.0538 (17)	0.0719 (16)	0.0417 (16)	−0.0282 (13)	0.0047 (13)	0.0035 (13)
O1	0.0484 (13)	0.0497 (11)	0.0405 (12)	−0.0197 (9)	0.0060 (10)	0.0007 (9)
S1	0.0539 (5)	0.0906 (6)	0.0417 (5)	−0.0418 (4)	0.0041 (4)	0.0022 (4)
S2	0.0562 (5)	0.0677 (5)	0.0411 (5)	−0.0300 (4)	0.0038 (4)	0.0003 (4)
S3	0.0612 (5)	0.0636 (5)	0.0419 (5)	−0.0326 (4)	0.0042 (4)	0.0040 (4)

Geometric parameters (Å, º) top

Br1—C24	1.871 (3)	C12—C13	1.400 (4)
C1—C2	1.370 (5)	C12—C15	1.471 (4)
C1—C6	1.382 (4)	C13—C14	1.376 (4)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.381 (6)	C14—S1	1.765 (3)
C2—H2	0.9300	C15—C16	1.361 (5)
C3—C4	1.385 (5)	C15—S2	1.736 (3)
C3—H3	0.9300	C16—C17	1.394 (5)
C4—C5	1.394 (4)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.363 (4)
C5—C6	1.403 (4)	C17—H17	0.9300
C5—N1	1.406 (4)	C18—C19	1.441 (4)
C6—S1	1.758 (3)	C18—S2	1.726 (3)
C7—N1	1.469 (4)	C19—N2	1.295 (4)
C7—C8	1.511 (6)	C19—O1	1.358 (4)
C7—H7A	0.9700	C20—N3	1.295 (4)
C7—H7B	0.9700	C20—O1	1.369 (4)
C8—H8A	0.9600	C20—C21	1.438 (5)
C8—H8B	0.9600	C21—C22	1.355 (5)
C8—H8C	0.9600	C21—S3	1.726 (3)
C9—C10	1.387 (4)	C22—C23	1.407 (5)
C9—C14	1.406 (4)	C22—H22	0.9300
C9—N1	1.417 (4)	C23—C24	1.344 (5)
C10—C11	1.379 (5)	C23—H23	0.9300
C10—H10	0.9300	C24—S3	1.715 (4)
C11—C12	1.385 (4)	N2—N3	1.405 (4)
C11—H11	0.9300

C2—C1—C6	120.6 (4)	C12—C13—H13	119.4
C2—C1—H1	119.7	C13—C14—C9	120.9 (3)
C6—C1—H1	119.7	C13—C14—S1	120.3 (2)
C1—C2—C3	119.5 (3)	C9—C14—S1	118.7 (2)
C1—C2—H2	120.2	C16—C15—C12	129.4 (3)
C3—C2—H2	120.2	C16—C15—S2	110.0 (2)
C2—C3—C4	120.6 (4)	C12—C15—S2	120.6 (2)
C2—C3—H3	119.7	C15—C16—C17	114.4 (3)
C4—C3—H3	119.7	C15—C16—H16	122.8
C3—C4—C5	120.7 (3)	C17—C16—H16	122.8
C3—C4—H4	119.6	C18—C17—C16	112.8 (3)
C5—C4—H4	119.6	C18—C17—H17	123.6
C4—C5—C6	117.6 (3)	C16—C17—H17	123.6
C4—C5—N1	122.9 (3)	C17—C18—C19	128.1 (3)
C6—C5—N1	119.5 (3)	C17—C18—S2	111.1 (3)
C1—C6—C5	120.9 (3)	C19—C18—S2	120.8 (2)
C1—C6—S1	120.4 (3)	N2—C19—O1	113.1 (3)
C5—C6—S1	118.6 (2)	N2—C19—C18	128.8 (3)
N1—C7—C8	112.8 (3)	O1—C19—C18	118.0 (3)
N1—C7—H7A	109.0	N3—C20—O1	112.7 (3)
C8—C7—H7A	109.0	N3—C20—C21	128.5 (3)
N1—C7—H7B	109.0	O1—C20—C21	118.8 (3)
C8—C7—H7B	109.0	C22—C21—C20	129.4 (3)
H7A—C7—H7B	107.8	C22—C21—S3	111.6 (3)
C7—C8—H8A	109.5	C20—C21—S3	119.0 (2)
C7—C8—H8B	109.5	C21—C22—C23	113.3 (3)
H8A—C8—H8B	109.5	C21—C22—H22	123.4
C7—C8—H8C	109.5	C23—C22—H22	123.4
H8A—C8—H8C	109.5	C24—C23—C22	111.5 (3)
H8B—C8—H8C	109.5	C24—C23—H23	124.2
C10—C9—C14	117.6 (3)	C22—C23—H23	124.2
C10—C9—N1	123.4 (3)	C23—C24—S3	113.5 (3)
C14—C9—N1	119.0 (3)	C23—C24—Br1	127.3 (3)
C11—C10—C9	121.1 (3)	S3—C24—Br1	119.19 (18)
C11—C10—H10	119.4	C5—N1—C9	117.9 (2)
C9—C10—H10	119.4	C5—N1—C7	119.3 (3)
C10—C11—C12	121.6 (3)	C9—N1—C7	118.0 (3)
C10—C11—H11	119.2	C19—N2—N3	106.0 (3)
C12—C11—H11	119.2	C20—N3—N2	106.1 (3)
C11—C12—C13	117.6 (3)	C19—O1—C20	102.1 (2)
C11—C12—C15	122.4 (3)	C6—S1—C14	98.95 (15)
C13—C12—C15	120.1 (3)	C18—S2—C15	91.68 (16)
C14—C13—C12	121.1 (3)	C24—S3—C21	90.13 (16)
C14—C13—H13	119.4

Experimental details

Crystal data
Chemical formula	C₂₄H₁₆BrN₃OS₃
M_r	538.49
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.4300 (5), 7.6019 (5), 22.1933 (14)
α, β, γ (°)	89.315 (4), 89.170 (4), 64.891 (4)
V (Å³)	1134.93 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.10 × 0.08 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.812, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	11444, 3972, 3138
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.136, 1.06
No. of reflections	3972
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.62

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), DIAMOND (Brandenburg, 2004) and SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and local programs.

Acknowledgements

The authors thank the China Natural Science Foundation (21120102036) and the National Basic Research Program of China (2009CB220009) for financial support.

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