4-[(5-Bromo-2-hy­droxy­benzyl­idene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione

Wu, X.; Yuan, C.-X.; Ma, L.; Zhai, K.-L.; Zhu, M.-L.

doi:10.1107/S1600536812019745

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1674

doi:10.1107/S1600536812019745

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4-[(5-Bromo-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione

Xin Wu,^a Cai-Xia Yuan,^b ^* Ling Ma,^c Kai-Lu Zhai ^d and Miao-Li Zhu ^b

^aCollege of Arts and Sciences, Shanxi Agricultural University, Taigu, Shanxi 030801, People's Republic of China, ^bInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China, ^cDepartment of Biochemistry and Molecular Biology, Shanxi Medical University, Taiyuan, Shanxi 030001, People's Republic of China, and ^dJincheng Tap Water Company, Jincheng, Shanxi 048000, People's Republic of China
^*Correspondence e-mail: cxyuan@sxu.edu.cn, miaoli@sxu.edu.cn

(Received 7 April 2012; accepted 2 May 2012; online 12 May 2012)

The asymmetric unit of the title compound, C₁₂H₁₃BrN₄OS, contains two independent molecules in which the dihedral angles between the triazole and benzene rings are 2.9 (3) and 7.5 (3)°. The thione group is of the form R₂C=S. An intramolecular O—H⋯N hydrogen bond occurs in each molecule. The crystal structure features weak N—H⋯S interactions and π–π stacking of the benzene rings [centroid–centroid distance = 3.667 (3) Å].

Related literature

For the pharmacological activity of 1,2,4-triazole-substituted and Schiff base compounds, see: Isloor et al. (2009 ); Ma et al. (2011 ). For copper complexes containing 1,2,4-triazole Schiff base ligands, see: Wen et al. (2004 ).

Experimental

Crystal data

C₁₂H₁₃BrN₄OS
M_r = 341.23
Triclinic, $[P \overline 1]$
a = 8.042 (5) Å
b = 13.187 (8) Å
c = 13.408 (8) Å
α = 97.406 (9)°
β = 92.956 (10)°
γ = 95.916 (9)°
V = 1399.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 298 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.458, T_max = 0.578
14278 measured reflections
4939 independent reflections
3061 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.102
S = 0.93
4939 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N4	0.82	1.93	2.644 (4)	145
O2—H2⋯N8	0.82	1.90	2.612 (4)	144
N1—H1A⋯S1ⁱ	0.86	2.46	3.300 (4)	164
N5—H5⋯S2ⁱⁱ	0.86	2.41	3.252 (4)	165
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019745/jj2128sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019745/jj2128Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019745/jj2128Isup3.cml

checkCIF report

Comment top

1,2,4-triazole and its derivatives possess a variety of pharmacological properties (Isloor et al., 2009). Schiff bases derived from substituted salicylaldehydes form numerous metal complexes (Wen et al., 2004). Also, copper complexes containing 1,2,4-triazole Schiff base ligands are potential inhibitors of PTP1B (protein tyrosine phosphatase 1B), TCPTP (T-cell protein tyrosine phosphatase), PTP-MEG2 (megakaryocyte protein tyrosine phosphatase) and SHP-1 (Src homology phosphatase 1) (Ma et al., 2011). In continuation of our work in this area, we report here the synthesis and crystal structure of the title compound, C₁₂H₁₃BrN₄OS, (I).

The title compound, (I), crystallizes with two independent molecules in the asymmetric unit (Fig. 1). The dihedral angles between the triazole and phenyl rings are 2.9 (3)° and 7.5 (3)°, respectively. The thione group is of the form R₂C=S with a Cdb\S distance of 1.673 (4)Å and 1.675 (4)Å indicating significant double bond character. Intramolecular O—H···N hydrogen bonds, weak N—H···S intermolecular interactions (Table 1) and π–π stacking of the benzene rings [centroid–centroid distance = 3.667 (3) Å] are observed that may influence crystal packing.

Related literature top

For the pharmacological activity of 1,2,4-triazole-substituted and Schiff base compounds, see: Isloor et al. (2009); Ma et al. (2011). For copper complexes containing 1,2,4-triazole Schiff base ligands, see: Wen et al. (2004).

Experimental top

0.5 mmol 5-Bromosalicylaldehyde in 10 ml of ethanol was added to a solution of 4-amino-5-propyl-1,2,4-triazole-3-thione (0.5 mmol) in 20 ml of ethanol, and then refluxed for 2 h. The resulting solution was filterd and recrystallized from ethanol. X-ray quality Yellow crystals of the title compound were formed upon slow evaporation of the resulting soluton.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound, (I), with displacement ellipsoids drawn at the 50% probability level. Dashed lines indicate O—H···N intramolecular hydrogen bonding.
	Fig. 2. Packing of the title compound, (I),viewed along the aaxis. Dashed lines indicate O—H···N intramolecular hydrogen bonds and weak N—H···S intermolecular interactions. Remaining hydrogen atoms have been removed for clarity.

4-[(5-Bromo-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole- 5(4H)-thione top

Crystal data top

C₁₂H₁₃BrN₄OS	Z = 4
M_r = 341.23	F(000) = 688
Triclinic, P1	D_x = 1.620 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.042 (5) Å	Cell parameters from 2374 reflections
b = 13.187 (8) Å	θ = 2.5–23.6°
c = 13.408 (8) Å	µ = 3.08 mm⁻¹
α = 97.406 (9)°	T = 298 K
β = 92.956 (10)°	Block, yellow
γ = 95.916 (9)°	0.30 × 0.25 × 0.20 mm
V = 1399.5 (15) Å³

Data collection top

Bruker SMART 1K CCD diffractometer	4939 independent reflections
Radiation source: fine-focus sealed tube	3061 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 11.72 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −15→15
T_min = 0.458, T_max = 0.578	l = −15→15
14278 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0516P)²] where P = (F_o² + 2F_c²)/3
4939 reflections	(Δ/σ)_max < 0.001
347 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₂H₁₃BrN₄OS	γ = 95.916 (9)°
M_r = 341.23	V = 1399.5 (15) Å³
Triclinic, P1	Z = 4
a = 8.042 (5) Å	Mo Kα radiation
b = 13.187 (8) Å	µ = 3.08 mm⁻¹
c = 13.408 (8) Å	T = 298 K
α = 97.406 (9)°	0.30 × 0.25 × 0.20 mm
β = 92.956 (10)°

Data collection top

Bruker SMART 1K CCD diffractometer	4939 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	3061 reflections with I > 2σ(I)
T_min = 0.458, T_max = 0.578	R_int = 0.055
14278 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 0.93	Δρ_max = 0.49 e Å⁻³
4939 reflections	Δρ_min = −0.55 e Å⁻³
347 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	0.38916 (7)	0.16296 (4)	0.59088 (4)	0.06736 (19)
S1	0.49656 (16)	0.40893 (8)	0.14062 (8)	0.0530 (3)
O1	0.1987 (5)	0.5771 (2)	0.5179 (2)	0.0666 (10)
H1	0.2089	0.5860	0.4590	0.100*
N1	0.4061 (5)	0.5891 (3)	0.0953 (2)	0.0521 (10)
H1A	0.4451	0.5805	0.0366	0.062*
N2	0.3314 (5)	0.6750 (3)	0.1302 (3)	0.0512 (10)
N3	0.3366 (4)	0.5663 (2)	0.2414 (2)	0.0378 (8)
N4	0.3044 (4)	0.5369 (2)	0.3350 (2)	0.0400 (8)
C1	0.4132 (5)	0.5203 (3)	0.1597 (3)	0.0389 (10)
C2	0.2882 (5)	0.6584 (3)	0.2197 (3)	0.0424 (10)
C3	0.1971 (6)	0.7272 (3)	0.2879 (3)	0.0462 (11)
H3A	0.2588	0.7428	0.3531	0.055*
H3B	0.0881	0.6922	0.2975	0.055*
C4	0.1740 (6)	0.8271 (3)	0.2457 (3)	0.0540 (12)
H4A	0.2832	0.8624	0.2370	0.065*
H4B	0.1143	0.8111	0.1799	0.065*
C5	0.0785 (7)	0.8980 (4)	0.3133 (4)	0.0833 (18)
H5A	−0.0316	0.8647	0.3197	0.125*
H5B	0.0695	0.9604	0.2844	0.125*
H5C	0.1368	0.9140	0.3786	0.125*
C6	0.3493 (5)	0.4529 (3)	0.3590 (3)	0.0420 (11)
H6	0.4027	0.4104	0.3131	0.050*
C7	0.3181 (5)	0.4230 (3)	0.4566 (3)	0.0368 (10)
C8	0.2452 (5)	0.4844 (3)	0.5321 (3)	0.0466 (11)
C9	0.2203 (6)	0.4511 (4)	0.6243 (3)	0.0554 (13)
H9	0.1734	0.4926	0.6743	0.066*
C10	0.2647 (6)	0.3566 (4)	0.6423 (3)	0.0562 (13)
H10	0.2475	0.3341	0.7043	0.067*
C11	0.3349 (5)	0.2955 (3)	0.5681 (3)	0.0458 (11)
C12	0.3633 (5)	0.3282 (3)	0.4773 (3)	0.0442 (11)
H12	0.4133	0.2868	0.4287	0.053*
Br2	0.51614 (6)	−0.08187 (4)	−0.31301 (4)	0.06348 (19)
S2	0.14032 (16)	0.37417 (8)	−0.08568 (8)	0.0509 (3)
O2	0.1831 (4)	−0.0214 (2)	0.0781 (2)	0.0544 (8)
H2	0.1680	0.0389	0.0943	0.082*
N6	−0.0208 (5)	0.3668 (3)	0.1823 (2)	0.0499 (9)
N5	0.0102 (5)	0.4074 (2)	0.0951 (2)	0.0516 (10)
H5	−0.0145	0.4674	0.0853	0.062*
N7	0.0963 (4)	0.2607 (2)	0.0741 (2)	0.0374 (8)
N8	0.1549 (4)	0.1671 (2)	0.0448 (2)	0.0385 (8)
C13	0.0814 (5)	0.3467 (3)	0.0267 (3)	0.0418 (10)
C14	0.0324 (5)	0.2768 (3)	0.1686 (3)	0.0413 (10)
C15	0.0280 (5)	0.2020 (3)	0.2411 (3)	0.0441 (11)
H15A	0.1416	0.1892	0.2590	0.053*
H15B	−0.0325	0.1375	0.2094	0.053*
C16	−0.0556 (6)	0.2392 (3)	0.3367 (3)	0.0495 (12)
H16A	0.0035	0.3043	0.3679	0.059*
H16B	−0.1700	0.2505	0.3191	0.059*
C17	−0.0559 (7)	0.1630 (4)	0.4107 (3)	0.0694 (15)
H17A	−0.1174	0.0991	0.3808	0.104*
H17B	−0.1078	0.1893	0.4701	0.104*
H17C	0.0573	0.1519	0.4285	0.104*
C18	0.2235 (5)	0.1495 (3)	−0.0384 (3)	0.0414 (10)
H18	0.2378	0.2006	−0.0799	0.050*
C19	0.2791 (5)	0.0495 (3)	−0.0681 (3)	0.0368 (10)
C20	0.2579 (5)	−0.0309 (3)	−0.0101 (3)	0.0395 (10)
C21	0.3146 (6)	−0.1252 (3)	−0.0421 (3)	0.0497 (12)
H21	0.3009	−0.1784	−0.0030	0.060*
C22	0.3909 (5)	−0.1398 (3)	−0.1314 (3)	0.0490 (11)
H22	0.4284	−0.2029	−0.1529	0.059*
C23	0.4117 (5)	−0.0604 (3)	−0.1893 (3)	0.0428 (10)
C24	0.3565 (5)	0.0322 (3)	−0.1588 (3)	0.0427 (11)
H24	0.3704	0.0846	−0.1989	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0834 (4)	0.0674 (3)	0.0629 (3)	0.0222 (3)	0.0151 (3)	0.0374 (3)
S1	0.0863 (9)	0.0448 (7)	0.0363 (6)	0.0296 (6)	0.0219 (6)	0.0124 (5)
O1	0.104 (3)	0.053 (2)	0.053 (2)	0.0347 (19)	0.038 (2)	0.0096 (16)
N1	0.081 (3)	0.045 (2)	0.039 (2)	0.027 (2)	0.028 (2)	0.0140 (17)
N2	0.076 (3)	0.042 (2)	0.043 (2)	0.0232 (19)	0.025 (2)	0.0148 (17)
N3	0.054 (2)	0.0365 (19)	0.0274 (18)	0.0125 (16)	0.0092 (16)	0.0128 (14)
N4	0.052 (2)	0.040 (2)	0.0313 (19)	0.0078 (17)	0.0147 (17)	0.0110 (15)
C1	0.052 (3)	0.039 (2)	0.030 (2)	0.011 (2)	0.008 (2)	0.0099 (18)
C2	0.048 (3)	0.043 (2)	0.040 (2)	0.011 (2)	0.010 (2)	0.0129 (19)
C3	0.057 (3)	0.039 (2)	0.049 (3)	0.018 (2)	0.021 (2)	0.015 (2)
C4	0.072 (3)	0.045 (3)	0.051 (3)	0.019 (2)	0.018 (3)	0.017 (2)
C5	0.115 (5)	0.056 (3)	0.097 (4)	0.045 (3)	0.057 (4)	0.028 (3)
C6	0.061 (3)	0.037 (2)	0.031 (2)	0.010 (2)	0.016 (2)	0.0079 (18)
C7	0.047 (3)	0.038 (2)	0.025 (2)	0.0033 (19)	0.0080 (19)	0.0050 (17)
C8	0.052 (3)	0.051 (3)	0.039 (3)	0.009 (2)	0.015 (2)	0.009 (2)
C9	0.074 (4)	0.061 (3)	0.034 (3)	0.013 (3)	0.023 (2)	0.003 (2)
C10	0.062 (3)	0.078 (4)	0.034 (3)	0.008 (3)	0.014 (2)	0.022 (2)
C11	0.052 (3)	0.049 (3)	0.040 (2)	0.004 (2)	0.009 (2)	0.020 (2)
C12	0.060 (3)	0.043 (2)	0.032 (2)	0.009 (2)	0.009 (2)	0.0082 (19)
Br2	0.0799 (4)	0.0558 (3)	0.0581 (3)	0.0235 (3)	0.0309 (3)	−0.0026 (2)
S2	0.0755 (9)	0.0429 (6)	0.0419 (6)	0.0249 (6)	0.0211 (6)	0.0133 (5)
O2	0.085 (2)	0.0426 (17)	0.0434 (18)	0.0200 (17)	0.0240 (17)	0.0158 (14)
N6	0.068 (3)	0.049 (2)	0.037 (2)	0.0223 (19)	0.0166 (19)	0.0066 (17)
N5	0.083 (3)	0.039 (2)	0.041 (2)	0.0294 (19)	0.023 (2)	0.0109 (16)
N7	0.051 (2)	0.0321 (18)	0.0332 (18)	0.0170 (16)	0.0127 (16)	0.0046 (14)
N8	0.051 (2)	0.0298 (18)	0.0369 (19)	0.0156 (16)	0.0104 (17)	0.0020 (14)
C13	0.055 (3)	0.034 (2)	0.038 (2)	0.015 (2)	0.007 (2)	0.0039 (18)
C14	0.049 (3)	0.041 (3)	0.036 (2)	0.013 (2)	0.013 (2)	0.0047 (19)
C15	0.055 (3)	0.044 (2)	0.037 (2)	0.015 (2)	0.010 (2)	0.0093 (19)
C16	0.063 (3)	0.053 (3)	0.034 (2)	0.015 (2)	0.014 (2)	0.002 (2)
C17	0.097 (4)	0.076 (4)	0.042 (3)	0.023 (3)	0.015 (3)	0.019 (3)
C18	0.055 (3)	0.036 (2)	0.037 (2)	0.014 (2)	0.014 (2)	0.0087 (18)
C19	0.044 (3)	0.031 (2)	0.037 (2)	0.0097 (19)	0.005 (2)	0.0057 (18)
C20	0.046 (3)	0.036 (2)	0.039 (2)	0.010 (2)	0.006 (2)	0.0096 (19)
C21	0.067 (3)	0.030 (2)	0.055 (3)	0.010 (2)	0.004 (3)	0.013 (2)
C22	0.060 (3)	0.037 (2)	0.053 (3)	0.021 (2)	0.007 (2)	0.001 (2)
C23	0.047 (3)	0.042 (2)	0.041 (2)	0.013 (2)	0.013 (2)	0.0011 (19)
C24	0.055 (3)	0.039 (2)	0.039 (2)	0.017 (2)	0.014 (2)	0.0085 (19)

Geometric parameters (Å, º) top

Br1—C11	1.902 (4)	Br2—C23	1.900 (4)
S1—C1	1.673 (4)	S2—C13	1.675 (4)
O1—C8	1.348 (5)	O2—C20	1.351 (4)
O1—H1	0.8200	O2—H2	0.8200
N1—C1	1.334 (5)	N6—C14	1.297 (5)
N1—N2	1.377 (4)	N6—N5	1.371 (4)
N1—H1A	0.8600	N5—C13	1.330 (5)
N2—C2	1.304 (5)	N5—H5	0.8600
N3—C2	1.375 (5)	N7—C13	1.381 (5)
N3—C1	1.385 (5)	N7—N8	1.384 (4)
N3—N4	1.390 (4)	N7—C14	1.391 (5)
N4—C6	1.274 (5)	N8—C18	1.274 (4)
C2—C3	1.479 (5)	C14—C15	1.470 (5)
C3—C4	1.524 (5)	C15—C16	1.527 (5)
C3—H3A	0.9700	C15—H15A	0.9700
C3—H3B	0.9700	C15—H15B	0.9700
C4—C5	1.512 (6)	C16—C17	1.500 (6)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—H5A	0.9600	C17—H17A	0.9600
C5—H5B	0.9600	C17—H17B	0.9600
C5—H5C	0.9600	C17—H17C	0.9600
C6—C7	1.442 (5)	C18—C19	1.450 (5)
C6—H6	0.9300	C18—H18	0.9300
C7—C12	1.394 (5)	C19—C20	1.395 (5)
C7—C8	1.404 (5)	C19—C24	1.398 (5)
C8—C9	1.381 (5)	C20—C21	1.392 (5)
C9—C10	1.378 (6)	C21—C22	1.374 (6)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.380 (6)	C22—C23	1.383 (6)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.366 (5)	C23—C24	1.363 (5)
C12—H12	0.9300	C24—H24	0.9300

C8—O1—H1	109.5	C20—O2—H2	109.5
C1—N1—N2	114.6 (3)	C14—N6—N5	104.5 (3)
C1—N1—H1A	122.7	C13—N5—N6	114.8 (3)
N2—N1—H1A	122.7	C13—N5—H5	122.6
C2—N2—N1	104.0 (3)	N6—N5—H5	122.6
C2—N3—C1	109.1 (3)	C13—N7—N8	133.1 (3)
C2—N3—N4	118.4 (3)	C13—N7—C14	108.8 (3)
C1—N3—N4	132.6 (3)	N8—N7—C14	118.0 (3)
C6—N4—N3	120.6 (3)	C18—N8—N7	121.2 (3)
N1—C1—N3	102.0 (3)	N5—C13—N7	102.2 (3)
N1—C1—S1	126.4 (3)	N5—C13—S2	126.8 (3)
N3—C1—S1	131.5 (3)	N7—C13—S2	131.0 (3)
N2—C2—N3	110.3 (3)	N6—C14—N7	109.7 (3)
N2—C2—C3	125.3 (4)	N6—C14—C15	125.9 (3)
N3—C2—C3	124.4 (3)	N7—C14—C15	124.3 (3)
C2—C3—C4	111.6 (3)	C14—C15—C16	112.5 (3)
C2—C3—H3A	109.3	C14—C15—H15A	109.1
C4—C3—H3A	109.3	C16—C15—H15A	109.1
C2—C3—H3B	109.3	C14—C15—H15B	109.1
C4—C3—H3B	109.3	C16—C15—H15B	109.1
H3A—C3—H3B	108.0	H15A—C15—H15B	107.8
C5—C4—C3	112.6 (3)	C17—C16—C15	111.8 (3)
C5—C4—H4A	109.1	C17—C16—H16A	109.3
C3—C4—H4A	109.1	C15—C16—H16A	109.3
C5—C4—H4B	109.1	C17—C16—H16B	109.3
C3—C4—H4B	109.1	C15—C16—H16B	109.3
H4A—C4—H4B	107.8	H16A—C16—H16B	107.9
C4—C5—H5A	109.5	C16—C17—H17A	109.5
C4—C5—H5B	109.5	C16—C17—H17B	109.5
H5A—C5—H5B	109.5	H17A—C17—H17B	109.5
C4—C5—H5C	109.5	C16—C17—H17C	109.5
H5A—C5—H5C	109.5	H17A—C17—H17C	109.5
H5B—C5—H5C	109.5	H17B—C17—H17C	109.5
N4—C6—C7	120.7 (4)	N8—C18—C19	119.7 (3)
N4—C6—H6	119.7	N8—C18—H18	120.1
C7—C6—H6	119.7	C19—C18—H18	120.1
C12—C7—C8	118.3 (4)	C20—C19—C24	118.3 (3)
C12—C7—C6	118.2 (3)	C20—C19—C18	122.8 (3)
C8—C7—C6	123.5 (4)	C24—C19—C18	118.9 (3)
O1—C8—C9	118.0 (4)	O2—C20—C21	117.4 (3)
O1—C8—C7	121.8 (4)	O2—C20—C19	122.4 (3)
C9—C8—C7	120.3 (4)	C21—C20—C19	120.2 (4)
C10—C9—C8	120.2 (4)	C22—C21—C20	120.2 (4)
C10—C9—H9	119.9	C22—C21—H21	119.9
C8—C9—H9	119.9	C20—C21—H21	119.9
C9—C10—C11	119.7 (4)	C21—C22—C23	119.8 (4)
C9—C10—H10	120.1	C21—C22—H22	120.1
C11—C10—H10	120.1	C23—C22—H22	120.1
C12—C11—C10	120.7 (4)	C24—C23—C22	120.6 (4)
C12—C11—Br1	119.3 (3)	C24—C23—Br2	120.0 (3)
C10—C11—Br1	120.0 (3)	C22—C23—Br2	119.4 (3)
C11—C12—C7	120.7 (4)	C23—C24—C19	120.9 (4)
C11—C12—H12	119.6	C23—C24—H24	119.6
C7—C12—H12	119.6	C19—C24—H24	119.6

C1—N1—N2—C2	−0.8 (5)	C14—N6—N5—C13	−0.2 (5)
C2—N3—N4—C6	−178.9 (4)	C13—N7—N8—C18	6.2 (6)
C1—N3—N4—C6	0.5 (6)	C14—N7—N8—C18	−176.1 (4)
N2—N1—C1—N3	0.2 (5)	N6—N5—C13—N7	0.2 (5)
N2—N1—C1—S1	−179.6 (3)	N6—N5—C13—S2	−178.1 (3)
C2—N3—C1—N1	0.5 (4)	N8—N7—C13—N5	177.7 (4)
N4—N3—C1—N1	−178.9 (4)	C14—N7—C13—N5	−0.1 (4)
C2—N3—C1—S1	−179.8 (3)	N8—N7—C13—S2	−4.1 (7)
N4—N3—C1—S1	0.8 (7)	C14—N7—C13—S2	178.1 (3)
N1—N2—C2—N3	1.1 (5)	N5—N6—C14—N7	0.0 (5)
N1—N2—C2—C3	−177.7 (4)	N5—N6—C14—C15	179.8 (4)
C1—N3—C2—N2	−1.0 (5)	C13—N7—C14—N6	0.1 (5)
N4—N3—C2—N2	178.5 (3)	N8—N7—C14—N6	−178.2 (3)
C1—N3—C2—C3	177.8 (4)	C13—N7—C14—C15	−179.7 (4)
N4—N3—C2—C3	−2.7 (6)	N8—N7—C14—C15	2.1 (6)
N2—C2—C3—C4	−5.9 (6)	N6—C14—C15—C16	2.6 (6)
N3—C2—C3—C4	175.5 (4)	N7—C14—C15—C16	−177.8 (4)
C2—C3—C4—C5	179.0 (4)	C14—C15—C16—C17	−178.8 (4)
N3—N4—C6—C7	179.1 (4)	N7—N8—C18—C19	−178.2 (3)
N4—C6—C7—C12	177.3 (4)	N8—C18—C19—C20	1.4 (6)
N4—C6—C7—C8	−3.0 (7)	N8—C18—C19—C24	−179.0 (4)
C12—C7—C8—O1	179.8 (4)	C24—C19—C20—O2	−179.4 (4)
C6—C7—C8—O1	0.0 (7)	C18—C19—C20—O2	0.3 (6)
C12—C7—C8—C9	0.3 (6)	C24—C19—C20—C21	0.7 (6)
C6—C7—C8—C9	−179.5 (4)	C18—C19—C20—C21	−179.7 (4)
O1—C8—C9—C10	179.6 (4)	O2—C20—C21—C22	179.6 (4)
C7—C8—C9—C10	−0.9 (7)	C19—C20—C21—C22	−0.4 (7)
C8—C9—C10—C11	0.3 (7)	C20—C21—C22—C23	0.2 (7)
C9—C10—C11—C12	1.0 (7)	C21—C22—C23—C24	−0.3 (7)
C9—C10—C11—Br1	−177.8 (4)	C21—C22—C23—Br2	−179.6 (3)
C10—C11—C12—C7	−1.6 (7)	C22—C23—C24—C19	0.6 (7)
Br1—C11—C12—C7	177.1 (3)	Br2—C23—C24—C19	179.9 (3)
C8—C7—C12—C11	1.0 (6)	C20—C19—C24—C23	−0.8 (6)
C6—C7—C12—C11	−179.3 (4)	C18—C19—C24—C23	179.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4	0.82	1.93	2.644 (4)	145
O2—H2···N8	0.82	1.90	2.612 (4)	144
N1—H1A···S1ⁱ	0.86	2.46	3.300 (4)	164
N5—H5···S2ⁱⁱ	0.86	2.41	3.252 (4)	165

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃BrN₄OS
M_r	341.23
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.042 (5), 13.187 (8), 13.408 (8)
α, β, γ (°)	97.406 (9), 92.956 (10), 95.916 (9)
V (Å³)	1399.5 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.458, 0.578
No. of measured, independent and observed [I > 2σ(I)] reflections	14278, 4939, 3061
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.102, 0.93
No. of reflections	4939
No. of parameters	347
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.55

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N4	0.82	1.93	2.644 (4)	144.9
O2—H2···N8	0.82	1.90	2.612 (4)	143.8
N1—H1A···S1ⁱ	0.86	2.46	3.300 (4)	164.1
N5—H5···S2ⁱⁱ	0.86	2.41	3.252 (4)	165.3

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China for Youth (grant No. 21001070), the Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 20111401110002) and the Natural Science Foundation of Shanxi Province of China (grant No. 2011021006–2).

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Isloor, A. M., Kalluraya, B. & Shetty, P. (2009). Eur. J. Med. Chem. 44, 3784–3787. Web of Science CrossRef PubMed CAS Google Scholar
Ma, L., Lu, L. P., Zhu, M. L., Wang, Q. M., Li, Y., Xing, S., Fu, X. Q., Gao, Z. Q. & Dong, Y. H. (2011). Dalton Trans. 40, 6532–6540. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2000). 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
Wen, L. R., Li, M., Wang, S. W., Zhang, S. S., Li, X. M. & Ou Yang, P. K. (2004). Chem. Res. Chin. Univ. 20, 722–724. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1674

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

4-[(5-Bromo-2-hy­dr­oxy­benzyl­­idene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(5-Bromo-2-hydroxybenzylidene)amino]-3-propyl-1H-1,2,4-triazole-5(4H)-thione