1,5-Bis[1-(4-bromo­phen­yl)ethyl­idene]thio­carbonohydrazide

Gao, Z.

doi:10.1107/S1600536813009720

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o723

https://doi.org/10.1107/S1600536813009720

Open

access

1,5-Bis[1-(4-bromophenyl)ethylidene]thiocarbonohydrazide

Zhiqing Gao ^a ^*

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: gaozq08@163.com

(Received 30 March 2013; accepted 9 April 2013; online 13 April 2013)

The asymmetric unit of the title compound, C₁₇H₁₆Br₂N₄S, contains two independent molecules in which the benzene rings form dihedral angles of 20.0 (1) and 55.3 (1)°. In the crystal, a pair of N—H⋯S hydrogen bonds link the two different independent molecules into a dimer.

Related literature

For the crystal structures of related compounds, see: Feng et al. (2011 ); Zhao (2011 ); Schmitt et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₆Br₂N₄S
M_r = 468.22
Triclinic, $[P \overline 1]$
a = 11.5800 (11) Å
b = 13.6950 (12) Å
c = 14.2860 (13) Å
α = 118.401 (2)°
β = 90.977 (1)°
γ = 108.404 (1)°
V = 1852.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 4.49 mm⁻¹
T = 298 K
0.43 × 0.37 × 0.33 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.248, T_max = 0.319
9457 measured reflections
6456 independent reflections
2949 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.214
S = 0.96
6456 reflections
438 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −1.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5B⋯S1	0.86	2.71	3.551 (8)	168
N1—H1⋯S2	0.86	2.69	3.551 (8)	174

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813009720/cv5398sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009720/cv5398Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009720/cv5398Isup3.cml

checkCIF report

Comment top

In a continuation of our structural study of thiocarbonohydrazides (Feng et al., 2011), we present here the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related thiocarbonohydrazides (Feng et al., 2011; Zhao, 2011; Schmitt et al., 2011). The benzene rings C4—C9 and C12—C17 form a dihedral angle of 20.0 (1)°, while benzene rings C21—C26 and C29—C34 form a dihedral angle of 55.3 (1)°.

In the crystal, intermolecular N—H···S hydrogen bonds link two independent molecules into dimer (Fig. 1).

Related literature top

For the crystal structures of related compounds, see: Feng et al. (2011); Zhao (2011); Schmitt et al. (2011).

Experimental top

p-Br-Acetophenone (1.0 mmol) and thiocarbohydrazide (0.5 mmol) were mixed in 25 ml flash in the methanol. After 6 h stirring at 354 K, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid.

Structure description top

In a continuation of our structural study of thiocarbonohydrazides (Feng et al., 2011), we present here the title compound (I).

In the crystal, intermolecular N—H···S hydrogen bonds link two independent molecules into dimer (Fig. 1).

For the crystal structures of related compounds, see: Feng et al. (2011); Zhao (2011); Schmitt et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A hydrogen-bonded (dashed lines) dimer in the asymmetric unit of (I) showing the atomic numbering and 50% probability displacement ellipsoids

1,5-Bis[1-(4-bromophenyl)ethylidene]thiocarbonohydrazide top

Crystal data top

C₁₇H₁₆Br₂N₄S	Z = 4
M_r = 468.22	F(000) = 928
Triclinic, P1	D_x = 1.679 Mg m⁻³
a = 11.5800 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.6950 (12) Å	Cell parameters from 2095 reflections
c = 14.2860 (13) Å	θ = 2.8–21.2°
α = 118.401 (2)°	µ = 4.49 mm⁻¹
β = 90.977 (1)°	T = 298 K
γ = 108.404 (1)°	Yellow, block
V = 1852.6 (3) Å³	0.43 × 0.37 × 0.33 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6456 independent reflections
Radiation source: fine-focus sealed tube	2949 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
phi and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→13
T_min = 0.248, T_max = 0.319	k = −16→14
9457 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.073	H-atom parameters constrained
wR(F²) = 0.214	w = 1/[σ²(F_o²) + (0.1033P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
6456 reflections	Δρ_max = 0.90 e Å⁻³
438 parameters	Δρ_min = −1.33 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0038 (8)

Crystal data top

C₁₇H₁₆Br₂N₄S	γ = 108.404 (1)°
M_r = 468.22	V = 1852.6 (3) Å³
Triclinic, P1	Z = 4
a = 11.5800 (11) Å	Mo Kα radiation
b = 13.6950 (12) Å	µ = 4.49 mm⁻¹
c = 14.2860 (13) Å	T = 298 K
α = 118.401 (2)°	0.43 × 0.37 × 0.33 mm
β = 90.977 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	6456 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2949 reflections with I > 2σ(I)
T_min = 0.248, T_max = 0.319	R_int = 0.081
9457 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.214	H-atom parameters constrained
S = 0.96	Δρ_max = 0.90 e Å⁻³
6456 reflections	Δρ_min = −1.33 e Å⁻³
438 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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	0.86326 (12)	1.60584 (12)	1.59389 (9)	0.0846 (5)
Br2	1.15040 (11)	0.55332 (10)	0.95650 (10)	0.0669 (4)
Br3	0.32652 (11)	0.37660 (11)	−0.03711 (8)	0.0723 (4)
Br4	−0.09677 (12)	1.33393 (11)	0.64953 (10)	0.0787 (5)
N5	0.4538 (7)	0.8654 (6)	0.6079 (6)	0.045 (2)
H5B	0.4943	0.8559	0.6519	0.055*
N6	0.4306 (7)	0.7886 (6)	0.4978 (6)	0.046 (2)
N7	0.3534 (7)	0.9606 (6)	0.5655 (6)	0.049 (2)
H7	0.3550	0.9157	0.4987	0.058*
N8	0.2919 (7)	1.0377 (6)	0.5921 (6)	0.047 (2)
S2	0.4295 (3)	1.0494 (3)	0.7779 (2)	0.0688 (9)
C18	0.4121 (9)	0.9556 (8)	0.6457 (7)	0.045 (2)
C19	0.4609 (8)	0.6957 (8)	0.4612 (7)	0.041 (2)
C20	0.5183 (9)	0.6633 (9)	0.5305 (7)	0.056 (3)
H20A	0.6005	0.7214	0.5670	0.084*
H20B	0.5226	0.5860	0.4861	0.084*
H20C	0.4688	0.6615	0.5834	0.084*
C21	0.4303 (8)	0.6187 (8)	0.3412 (7)	0.042 (2)
C22	0.4345 (9)	0.6678 (8)	0.2735 (8)	0.052 (3)
H22	0.4588	0.7501	0.3053	0.062*
C23	0.4042 (9)	0.5988 (9)	0.1630 (8)	0.057 (3)
H23	0.4086	0.6328	0.1196	0.069*
C24	0.3668 (8)	0.4769 (9)	0.1180 (7)	0.047 (3)
C25	0.3645 (9)	0.4233 (9)	0.1799 (8)	0.051 (3)
H25	0.3407	0.3409	0.1470	0.061*
C26	0.3982 (9)	0.4952 (8)	0.2910 (8)	0.050 (3)
H26	0.3998	0.4610	0.3335	0.060*
C27	0.2443 (9)	1.0463 (7)	0.5156 (8)	0.044 (2)
C28	0.2551 (10)	0.9804 (9)	0.3973 (8)	0.061 (3)
H28A	0.3316	0.9665	0.3933	0.091*
H28B	0.2540	1.0277	0.3651	0.091*
H28C	0.1865	0.9053	0.3588	0.091*
C29	0.1686 (8)	1.1214 (8)	0.5468 (7)	0.041 (2)
C30	0.1683 (9)	1.1928 (8)	0.6561 (8)	0.051 (3)
H30	0.2209	1.1971	0.7091	0.061*
C31	0.0914 (10)	1.2570 (9)	0.6868 (9)	0.058 (3)
H31	0.0928	1.3050	0.7600	0.069*
C32	0.0137 (9)	1.2497 (8)	0.6096 (8)	0.048 (3)
C33	0.0121 (10)	1.1817 (9)	0.5017 (9)	0.061 (3)
H33	−0.0413	1.1780	0.4497	0.073*
C34	0.0898 (10)	1.1187 (9)	0.4703 (8)	0.053 (3)
H34	0.0896	1.0736	0.3968	0.064*
C1	0.6961 (9)	0.9711 (8)	0.9249 (7)	0.044 (2)
C2	0.6406 (8)	1.2301 (8)	1.1112 (7)	0.042 (2)
C3	0.5534 (10)	1.2427 (9)	1.0443 (8)	0.061 (3)
H3A	0.5938	1.2585	0.9922	0.091*
H3B	0.5283	1.3077	1.0904	0.091*
H3C	0.4816	1.1702	1.0071	0.091*
C4	0.6932 (8)	1.3211 (8)	1.2269 (7)	0.043 (2)
C5	0.6906 (8)	1.4327 (8)	1.2704 (7)	0.044 (2)
H5A	0.6540	1.4526	1.2269	0.053*
C6	0.7420 (9)	1.5178 (9)	1.3795 (8)	0.056 (3)
H6	0.7399	1.5939	1.4082	0.068*
C7	0.7958 (9)	1.4894 (9)	1.4448 (7)	0.051 (3)
C8	0.7975 (10)	1.3767 (10)	1.4055 (8)	0.066 (3)
H8	0.8305	1.3562	1.4504	0.079*
C9	0.7471 (10)	1.2936 (10)	1.2942 (8)	0.059 (3)
H9	0.7500	1.2177	1.2649	0.071*
C10	0.9075 (9)	0.9240 (8)	1.0604 (7)	0.042 (2)
C11	0.9352 (11)	1.0257 (10)	1.1749 (8)	0.076 (4)
H11A	0.9116	1.0871	1.1756	0.114*
H11B	1.0225	1.0573	1.2043	0.114*
H11C	0.8893	0.9976	1.2182	0.114*
C12	0.9696 (8)	0.8369 (8)	1.0347 (7)	0.042 (2)
C13	0.9539 (9)	0.7456 (8)	0.9292 (7)	0.050 (3)
H13	0.9045	0.7403	0.8736	0.060*
C14	1.0085 (10)	0.6628 (9)	0.9037 (8)	0.056 (3)
H14	0.9979	0.6037	0.8320	0.067*
C15	1.0793 (9)	0.6687 (9)	0.9861 (9)	0.050 (3)
C16	1.0998 (10)	0.7599 (10)	1.0913 (8)	0.062 (3)
H16	1.1509	0.7664	1.1465	0.074*
C17	1.0443 (10)	0.8407 (10)	1.1137 (8)	0.061 (3)
H17	1.0573	0.9010	1.1854	0.073*
S1	0.6625 (3)	0.8667 (2)	0.79389 (19)	0.0573 (8)
N1	0.6438 (7)	1.0560 (6)	0.9636 (6)	0.046 (2)
H1	0.5879	1.0546	0.9220	0.055*
N2	0.6838 (7)	1.1437 (7)	1.0710 (6)	0.045 (2)
N3	0.7716 (7)	0.9799 (7)	1.0024 (6)	0.051 (2)
H3	0.7833	1.0366	1.0681	0.061*
N4	0.8306 (7)	0.9031 (7)	0.9815 (6)	0.046 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0993 (10)	0.0729 (10)	0.0402 (7)	0.0114 (7)	0.0123 (6)	0.0105 (6)
Br2	0.0741 (8)	0.0582 (8)	0.0797 (9)	0.0427 (6)	0.0312 (6)	0.0316 (6)
Br3	0.0858 (9)	0.0716 (9)	0.0357 (6)	0.0361 (7)	0.0156 (5)	0.0051 (6)
Br4	0.0866 (9)	0.0617 (9)	0.0857 (9)	0.0481 (7)	0.0081 (7)	0.0234 (7)
N5	0.060 (5)	0.032 (5)	0.037 (5)	0.026 (4)	0.007 (4)	0.007 (4)
N6	0.059 (5)	0.031 (5)	0.038 (5)	0.022 (4)	0.011 (4)	0.008 (4)
N7	0.064 (6)	0.038 (5)	0.036 (5)	0.030 (4)	0.004 (4)	0.006 (4)
N8	0.067 (6)	0.035 (5)	0.034 (5)	0.032 (4)	0.003 (4)	0.006 (4)
S2	0.112 (3)	0.0566 (19)	0.0339 (15)	0.0562 (17)	0.0061 (14)	0.0046 (13)
C18	0.056 (6)	0.031 (6)	0.042 (6)	0.023 (5)	0.006 (5)	0.009 (5)
C19	0.049 (6)	0.035 (6)	0.041 (6)	0.023 (5)	0.012 (4)	0.015 (5)
C20	0.074 (7)	0.052 (7)	0.039 (6)	0.037 (6)	0.013 (5)	0.011 (5)
C21	0.040 (6)	0.038 (6)	0.043 (6)	0.018 (5)	0.012 (4)	0.014 (5)
C22	0.070 (7)	0.031 (6)	0.043 (6)	0.020 (5)	0.007 (5)	0.009 (5)
C23	0.074 (8)	0.056 (8)	0.048 (7)	0.029 (6)	0.023 (5)	0.028 (6)
C24	0.037 (6)	0.044 (7)	0.043 (6)	0.023 (5)	0.013 (4)	0.006 (5)
C25	0.062 (7)	0.034 (6)	0.050 (7)	0.024 (5)	0.015 (5)	0.014 (5)
C26	0.057 (7)	0.025 (6)	0.062 (7)	0.014 (5)	0.010 (5)	0.019 (5)
C27	0.053 (6)	0.017 (5)	0.045 (6)	0.010 (4)	−0.002 (5)	0.006 (4)
C28	0.067 (7)	0.065 (8)	0.051 (7)	0.033 (6)	0.013 (5)	0.025 (6)
C29	0.044 (6)	0.030 (6)	0.049 (6)	0.011 (4)	0.011 (4)	0.021 (5)
C30	0.067 (7)	0.043 (6)	0.041 (6)	0.030 (5)	0.009 (5)	0.013 (5)
C31	0.071 (8)	0.039 (7)	0.056 (7)	0.029 (6)	0.015 (6)	0.014 (5)
C32	0.059 (7)	0.030 (6)	0.053 (7)	0.024 (5)	0.000 (5)	0.016 (5)
C33	0.072 (8)	0.042 (7)	0.066 (8)	0.021 (6)	−0.004 (6)	0.026 (6)
C34	0.071 (7)	0.037 (6)	0.045 (6)	0.018 (5)	−0.008 (5)	0.017 (5)
C1	0.051 (6)	0.032 (6)	0.041 (6)	0.013 (5)	0.007 (5)	0.015 (5)
C2	0.041 (6)	0.046 (6)	0.042 (6)	0.022 (5)	0.010 (4)	0.020 (5)
C3	0.076 (8)	0.068 (8)	0.039 (6)	0.046 (6)	0.017 (5)	0.016 (5)
C4	0.050 (6)	0.032 (6)	0.042 (6)	0.020 (5)	0.008 (4)	0.013 (5)
C5	0.056 (7)	0.033 (6)	0.041 (6)	0.020 (5)	0.015 (4)	0.015 (5)
C6	0.066 (7)	0.031 (6)	0.060 (7)	0.015 (5)	0.020 (6)	0.015 (5)
C7	0.063 (7)	0.040 (7)	0.034 (6)	0.014 (5)	0.012 (5)	0.009 (5)
C8	0.085 (9)	0.068 (9)	0.048 (7)	0.036 (7)	0.015 (6)	0.026 (6)
C9	0.075 (8)	0.057 (7)	0.049 (7)	0.034 (6)	0.019 (5)	0.021 (6)
C10	0.061 (7)	0.031 (6)	0.036 (6)	0.024 (5)	0.016 (5)	0.013 (5)
C11	0.105 (9)	0.067 (8)	0.043 (6)	0.050 (7)	−0.008 (6)	0.007 (6)
C12	0.044 (6)	0.027 (5)	0.045 (6)	0.016 (4)	0.015 (4)	0.009 (5)
C13	0.065 (7)	0.041 (6)	0.027 (5)	0.019 (5)	0.008 (4)	0.006 (5)
C14	0.073 (8)	0.049 (7)	0.041 (6)	0.034 (6)	0.016 (5)	0.011 (5)
C15	0.046 (6)	0.047 (7)	0.066 (7)	0.026 (5)	0.019 (5)	0.030 (6)
C16	0.073 (8)	0.064 (8)	0.043 (7)	0.037 (6)	0.007 (5)	0.016 (6)
C17	0.085 (8)	0.063 (8)	0.035 (6)	0.049 (6)	0.009 (5)	0.011 (5)
S1	0.081 (2)	0.0479 (17)	0.0348 (14)	0.0368 (15)	0.0041 (12)	0.0074 (12)
N1	0.055 (5)	0.038 (5)	0.041 (5)	0.026 (4)	0.005 (4)	0.013 (4)
N2	0.050 (5)	0.047 (5)	0.032 (4)	0.028 (4)	0.017 (4)	0.009 (4)
N3	0.074 (6)	0.037 (5)	0.035 (5)	0.030 (4)	0.002 (4)	0.006 (4)
N4	0.052 (5)	0.046 (5)	0.038 (5)	0.030 (4)	0.009 (4)	0.012 (4)

Geometric parameters (Å, º) top

Br1—C7	1.902 (9)	C33—H33	0.9300
Br2—C15	1.885 (10)	C34—H34	0.9300
Br3—C24	1.918 (9)	C1—N3	1.333 (11)
Br4—C32	1.903 (10)	C1—N1	1.367 (11)
N5—C18	1.342 (11)	C1—S1	1.667 (9)
N5—N6	1.374 (10)	C2—N2	1.310 (11)
N5—H5B	0.8600	C2—C4	1.478 (12)
N6—C19	1.292 (11)	C2—C3	1.482 (12)
N7—C18	1.363 (11)	C3—H3A	0.9600
N7—N8	1.366 (10)	C3—H3B	0.9600
N7—H7	0.8600	C3—H3C	0.9600
N8—C27	1.285 (11)	C4—C5	1.360 (12)
S2—C18	1.666 (9)	C4—C9	1.388 (13)
C19—C21	1.484 (12)	C5—C6	1.394 (13)
C19—C20	1.484 (12)	C5—H5A	0.9300
C20—H20A	0.9600	C6—C7	1.373 (14)
C20—H20B	0.9600	C6—H6	0.9300
C20—H20C	0.9600	C7—C8	1.376 (14)
C21—C26	1.397 (12)	C8—C9	1.412 (13)
C21—C22	1.410 (13)	C8—H8	0.9300
C22—C23	1.364 (13)	C9—H9	0.9300
C22—H22	0.9300	C10—N4	1.282 (11)
C23—C24	1.378 (13)	C10—C12	1.486 (12)
C23—H23	0.9300	C10—C11	1.501 (13)
C24—C25	1.388 (13)	C11—H11A	0.9600
C25—C26	1.375 (13)	C11—H11B	0.9600
C25—H25	0.9300	C11—H11C	0.9600
C26—H26	0.9300	C12—C17	1.382 (13)
C27—C29	1.474 (13)	C12—C13	1.386 (12)
C27—C28	1.522 (13)	C13—C14	1.374 (13)
C28—H28A	0.9600	C13—H13	0.9300
C28—H28B	0.9600	C14—C15	1.378 (13)
C28—H28C	0.9600	C14—H14	0.9300
C29—C34	1.391 (12)	C15—C16	1.374 (13)
C29—C30	1.395 (13)	C16—C17	1.363 (14)
C30—C31	1.378 (13)	C16—H16	0.9300
C30—H30	0.9300	C17—H17	0.9300
C31—C32	1.357 (13)	N1—N2	1.372 (10)
C31—H31	0.9300	N1—H1	0.8600
C32—C33	1.366 (14)	N3—N4	1.350 (10)
C33—C34	1.374 (14)	N3—H3	0.8600

C18—N5—N6	118.9 (8)	N3—C1—N1	113.2 (8)
C18—N5—H5B	120.5	N3—C1—S1	125.1 (8)
N6—N5—H5B	120.5	N1—C1—S1	121.7 (7)
C19—N6—N5	119.3 (8)	N2—C2—C4	115.2 (8)
C18—N7—N8	119.5 (8)	N2—C2—C3	123.0 (8)
C18—N7—H7	120.3	C4—C2—C3	121.5 (8)
N8—N7—H7	120.3	C2—C3—H3A	109.5
C27—N8—N7	118.1 (8)	C2—C3—H3B	109.5
N5—C18—N7	113.3 (8)	H3A—C3—H3B	109.5
N5—C18—S2	122.5 (7)	C2—C3—H3C	109.5
N7—C18—S2	124.2 (7)	H3A—C3—H3C	109.5
N6—C19—C21	114.5 (8)	H3B—C3—H3C	109.5
N6—C19—C20	124.5 (8)	C5—C4—C9	118.4 (9)
C21—C19—C20	121.0 (8)	C5—C4—C2	121.7 (9)
C19—C20—H20A	109.5	C9—C4—C2	120.0 (9)
C19—C20—H20B	109.5	C4—C5—C6	120.8 (9)
H20A—C20—H20B	109.5	C4—C5—H5A	119.6
C19—C20—H20C	109.5	C6—C5—H5A	119.6
H20A—C20—H20C	109.5	C7—C6—C5	120.1 (9)
H20B—C20—H20C	109.5	C7—C6—H6	119.9
C26—C21—C22	117.5 (9)	C5—C6—H6	119.9
C26—C21—C19	121.3 (9)	C6—C7—C8	121.3 (9)
C22—C21—C19	121.1 (8)	C6—C7—Br1	119.5 (8)
C23—C22—C21	122.3 (9)	C8—C7—Br1	119.1 (8)
C23—C22—H22	118.8	C7—C8—C9	117.0 (10)
C21—C22—H22	118.8	C7—C8—H8	121.5
C22—C23—C24	117.7 (10)	C9—C8—H8	121.5
C22—C23—H23	121.2	C4—C9—C8	122.3 (10)
C24—C23—H23	121.2	C4—C9—H9	118.9
C23—C24—C25	122.8 (9)	C8—C9—H9	118.9
C23—C24—Br3	119.1 (8)	N4—C10—C12	116.0 (8)
C25—C24—Br3	117.9 (7)	N4—C10—C11	125.2 (9)
C26—C25—C24	118.3 (9)	C12—C10—C11	118.7 (8)
C26—C25—H25	120.9	C10—C11—H11A	109.5
C24—C25—H25	120.9	C10—C11—H11B	109.5
C25—C26—C21	121.3 (9)	H11A—C11—H11B	109.5
C25—C26—H26	119.4	C10—C11—H11C	109.5
C21—C26—H26	119.4	H11A—C11—H11C	109.5
N8—C27—C29	115.9 (9)	H11B—C11—H11C	109.5
N8—C27—C28	125.0 (9)	C17—C12—C13	116.2 (9)
C29—C27—C28	119.0 (8)	C17—C12—C10	122.4 (8)
C27—C28—H28A	109.5	C13—C12—C10	121.4 (9)
C27—C28—H28B	109.5	C14—C13—C12	122.5 (9)
H28A—C28—H28B	109.5	C14—C13—H13	118.8
C27—C28—H28C	109.5	C12—C13—H13	118.8
H28A—C28—H28C	109.5	C13—C14—C15	119.0 (10)
H28B—C28—H28C	109.5	C13—C14—H14	120.5
C34—C29—C30	117.6 (9)	C15—C14—H14	120.5
C34—C29—C27	122.3 (9)	C16—C15—C14	120.2 (9)
C30—C29—C27	119.9 (8)	C16—C15—Br2	119.1 (8)
C31—C30—C29	121.0 (9)	C14—C15—Br2	120.8 (8)
C31—C30—H30	119.5	C17—C16—C15	119.3 (10)
C29—C30—H30	119.5	C17—C16—H16	120.4
C32—C31—C30	119.6 (10)	C15—C16—H16	120.4
C32—C31—H31	120.2	C16—C17—C12	122.9 (10)
C30—C31—H31	120.2	C16—C17—H17	118.6
C31—C32—C33	121.1 (10)	C12—C17—H17	118.6
C31—C32—Br4	120.5 (8)	C1—N1—N2	117.6 (7)
C33—C32—Br4	118.4 (7)	C1—N1—H1	121.2
C32—C33—C34	119.7 (9)	N2—N1—H1	121.2
C32—C33—H33	120.1	C2—N2—N1	120.2 (8)
C34—C33—H33	120.1	C1—N3—N4	122.5 (8)
C33—C34—C29	120.9 (10)	C1—N3—H3	118.8
C33—C34—H34	119.5	N4—N3—H3	118.8
C29—C34—H34	119.5	C10—N4—N3	117.5 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···S1	0.86	2.71	3.551 (8)	168
N1—H1···S2	0.86	2.69	3.551 (8)	174

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆Br₂N₄S
M_r	468.22
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	11.5800 (11), 13.6950 (12), 14.2860 (13)
α, β, γ (°)	118.401 (2), 90.977 (1), 108.404 (1)
V (Å³)	1852.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.49
Crystal size (mm)	0.43 × 0.37 × 0.33

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.248, 0.319
No. of measured, independent and observed [I > 2σ(I)] reflections	9457, 6456, 2949
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.214, 0.96
No. of reflections	6456
No. of parameters	438
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −1.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5B···S1	0.86	2.71	3.551 (8)	168
N1—H1···S2	0.86	2.69	3.551 (8)	174

Acknowledgements

The author acknowledges financial support by Dongchang College, Liaocheng University.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Feng, L., Ji, H., Wang, R., Ge, H. & Li, L. (2011). Acta Cryst. E67, o1514. Web of Science CSD CrossRef IUCr Journals Google Scholar
Schmitt, B., Gerber, T., Hosten, E. & Betz, R. (2011). Acta Cryst. E67, o2206–o2207. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhao, X. (2011). Acta Cryst. E67, o2132. Web of Science CSD CrossRef IUCr Journals Google Scholar