4-(4-Bromo­benzyl­ideneamino)-1-(diphenyl­amino­meth­yl)-3-[1-(4-isobutyl­phen­yl)eth­yl]-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Jebas, S.R.; Sujith, K.V.; Patil, P.S.; Kalluraya, B.; Dharmaprakash, S.M.

doi:10.1107/S1600536808012713

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1001-o1002

doi:10.1107/S1600536808012713

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4-(4-Bromobenzylideneamino)-1-(diphenylaminomethyl)-3-[1-(4-isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ K. V. Sujith,^b P. S. Patil,^c B. Kalluraya ^b and S. M Dharmaprakash ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 April 2008; accepted 30 April 2008; online 7 May 2008)

In the title compound, C₃₄H₃₄BrN₅S, the two phenyl rings of the diphenylaminomethyl group are inclined at an angle of 73.86 (8)° and they form dihedral angles of 74.04 (8) and 48.74 (8)° with the triazole ring. Intramolecular C—H⋯S hydrogen bonds generate S(6) and S(5) ring motifs. The crystal structure is stabilized by weak C—H⋯π interactions.

Related literature

For related literature, see: Dave et al. (2007 ); Kalluraya et al. (2003 , 2004 , 2007 ); Kane et al. (1990 ). For literature on Mannich bases, see: Kalluraya et al. (2001 ). For bond-length data, see: Allen et al. (1987 ). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₄H₃₄BrN₅S
M_r = 624.63
Monoclinic, P 2₁ /c
a = 10.9672 (1) Å
b = 9.7833 (1) Å
c = 28.6210 (3) Å
β = 105.966 (1)°
V = 2952.44 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.50 mm⁻¹
T = 100.0 (1) K
0.35 × 0.31 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.623, T_max = 0.684
55283 measured reflections
13248 independent reflections
7914 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.098
S = 1.01
13248 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯S1	0.93	2.52	3.217 (2)	132
C22—H22B⋯S1	0.97	2.80	3.232 (2)	108
C6—H6A⋯Cg1ⁱ	0.93	2.81	3.717 (2)	165
C21—H21C⋯Cg2ⁱⁱ	0.96	2.89	3.829 (2)	168
Symmetry codes: (i) -x+1, -y, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 and Cg2 are the centroids of the C11–C16 and C23–C28 rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012713/ci2592sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012713/ci2592Isup2.hkl

checkCIF report

Comment top

Nitrogen-containing heterocyclic molecules constitute the largest portion of chemical entities, which are part of many natural products, fine chemicals, and biologically active pharmaceuticals vital for enhancing the quality of life (Kalluraya et al. 2003, 2007; Kane et al., 1990). Mannich bases are a class of heterocycles, which have attracted significant interest in medicinal chemistry (Kalluraya et al., 2004). Among the Mannich bases, 1,2,4-triazole derivatives have attracted considerable attention because of their wide variety of biological activities, such as antineoplastic, analgesic and antibiotic activity (Dave et al., 2007). Mannich bases are obtained by condensing an amine, formaldehyde and a compound containing active hydrogen atom (Kalluraya et al., 2001). It is interesting to note that the reaction is highly regioselective and furnishes only the N-Mannich base and none of the S-Mannich derivatives, though the intermediate Schiff bases can exist in the thiol-thione tautomeric equilibrium. In view of these impressive array of properties exhibited by Mannich bases, the crystal structure of the title compound is reported here.

Bond lengths and angles in the title compound have normal values (Allen et al., 1987). The triazole ring is planar with a maximium deviation of 0.010 (2) Å for atom C1. The planes through the C4—C9, C11—C16, C23—C28 and C29—C34 rings form dihedral angles of 25.10 (8), 81.35 (8), 74.04 (8) and 48.74 (8)°, respectively, with the the triazole ring. Weak C—H···S hydrogen bonds generating S(6) and S(5) ring motifs (Bernstein et al.,(1995) are observed in the molecular structure.

The crystal packing is stabilized by weak C—H···π interactions involving the C11–C16 (centroid Cg1) and C23–C28 (centroid Cg2) rings (Table 1).

Related literature top

For related literature, see: Dave et al. (2007); Kalluraya et al. (2003,2004,2007); Kane et al. (1990). For literature on Mannich bases, see: Kalluraya et al. (2001). For bond-length data, see: Allen et al. (1987). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995). Cg1 and Cg2 are the centroids of the C11-C16 and C23–C28 rings, respectively.

Experimental top

The title compound, a Mannich base, was obtained by the aminomethylation of a Schiff base, 4-{[(4-bromophenyl)methylene]amino}-5-[1-(4-isobutylphenyl)ethyl]-3-mercapto- 1,2,4-triazole which was in turn obtained by refluxing 4-amino-3-mercapto-5- [1-(4-isobutylphenyl)ethyl]-1,2,4-triazole (0.01 mol) and 4-bromo benzaldehyde (0.01 mol) in ethanol (30 ml) by adding 2 drops of concentrated sulfuric acid for 3 h. A mixture of the obtained Schiff base (0.01 mol), formaldehyde (40%, 1 ml) and diphenyl amine (0.01 mol) in ethanol (50 ml) was stirred at room temperature for 16 h. The solid product was collected by filtration, washed with ethanol and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from an acetone-N,N-dimethylformamide (DMF) (1:3) solution by slow evaporation (yield 68%; m.p. 381–382 K). Analysis (%) for C₃₄H₃₄N₅BrS found (calculated): C 65.23 (65.38), H 5.33 (5.44), N 11.21 (11.17).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonds.

4-(4-Bromobenzylideneamino)-1-(diphenylaminomethyl)-3-[1-(4- isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₃₄H₃₄BrN₅S	F(000) = 1296
M_r = 624.63	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8665 reflections
a = 10.9672 (1) Å	θ = 2.2–29.2°
b = 9.7833 (1) Å	µ = 1.50 mm⁻¹
c = 28.6210 (3) Å	T = 100 K
β = 105.966 (1)°	Block, colourless
V = 2952.44 (5) Å³	0.35 × 0.31 × 0.27 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	13248 independent reflections
Radiation source: fine-focus sealed tube	7914 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ϕ and ω scans	θ_max = 35.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −17→17
T_min = 0.623, T_max = 0.684	k = −15→15
55283 measured reflections	l = −46→46

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) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0352P)² + 0.5449P] where P = (F_o² + 2F_c²)/3
13248 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

C₃₄H₃₄BrN₅S	V = 2952.44 (5) Å³
M_r = 624.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9672 (1) Å	µ = 1.50 mm⁻¹
b = 9.7833 (1) Å	T = 100 K
c = 28.6210 (3) Å	0.35 × 0.31 × 0.27 mm
β = 105.966 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	13248 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	7914 reflections with I > 2σ(I)
T_min = 0.623, T_max = 0.684	R_int = 0.059
55283 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.02	Δρ_max = 0.46 e Å⁻³
13248 reflections	Δρ_min = −0.57 e Å⁻³
372 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.543981 (15)	−0.004817 (17)	−0.133261 (6)	0.02529 (5)
S1	0.15515 (5)	−0.27622 (4)	0.091481 (16)	0.02758 (10)
N1	0.11707 (12)	−0.00549 (12)	0.06174 (4)	0.0177 (2)
N2	0.01822 (12)	0.07970 (13)	0.11283 (5)	0.0194 (3)
N3	0.05163 (13)	−0.05530 (13)	0.12340 (4)	0.0192 (3)
N4	0.05997 (13)	−0.03122 (13)	0.20801 (5)	0.0213 (3)
N5	0.16650 (12)	0.00579 (12)	0.02217 (4)	0.0186 (2)
C1	0.11076 (15)	−0.11338 (15)	0.09263 (5)	0.0194 (3)
C2	0.05841 (14)	0.10666 (15)	0.07525 (5)	0.0176 (3)
C3	0.25133 (14)	−0.08055 (15)	0.01851 (5)	0.0191 (3)
H3A	0.2737	−0.1521	0.0406	0.023*
C4	0.31254 (14)	−0.06601 (15)	−0.02038 (5)	0.0170 (3)
C5	0.41316 (15)	−0.15262 (15)	−0.02088 (5)	0.0193 (3)
H5A	0.4342	−0.2231	0.0017	0.023*
C6	0.48243 (15)	−0.13606 (15)	−0.05424 (5)	0.0194 (3)
H6A	0.5502	−0.1935	−0.0539	0.023*
C7	0.44857 (15)	−0.03203 (15)	−0.08809 (5)	0.0194 (3)
C8	0.34706 (15)	0.05398 (16)	−0.08930 (5)	0.0202 (3)
H8A	0.3250	0.1224	−0.1127	0.024*
C9	0.27910 (15)	0.03763 (15)	−0.05571 (5)	0.0195 (3)
H9A	0.2111	0.0951	−0.0564	0.023*
C10	0.04978 (14)	0.24247 (15)	0.05043 (5)	0.0196 (3)
H10A	0.0236	0.2270	0.0152	0.023*
C11	0.17723 (14)	0.31489 (14)	0.06341 (5)	0.0181 (3)
C12	0.21998 (15)	0.37842 (15)	0.02736 (5)	0.0203 (3)
H12A	0.1743	0.3683	−0.0050	0.024*
C13	0.32967 (16)	0.45656 (16)	0.03905 (6)	0.0220 (3)
H13A	0.3565	0.4979	0.0143	0.026*
C14	0.40058 (15)	0.47425 (15)	0.08733 (6)	0.0198 (3)
C15	0.35851 (15)	0.40810 (16)	0.12319 (6)	0.0218 (3)
H15A	0.4047	0.4170	0.1556	0.026*
C16	0.24913 (15)	0.32926 (16)	0.11149 (5)	0.0208 (3)
H16A	0.2235	0.2855	0.1361	0.025*
C17	−0.05057 (16)	0.33197 (16)	0.06350 (6)	0.0258 (3)
H17A	−0.1306	0.2851	0.0550	0.039*
H17B	−0.0586	0.4165	0.0459	0.039*
H17C	−0.0254	0.3504	0.0978	0.039*
C18	0.51856 (15)	0.56133 (16)	0.09975 (6)	0.0228 (3)
H18A	0.5288	0.6009	0.1317	0.027*
H18B	0.5065	0.6360	0.0766	0.027*
C19	0.64115 (15)	0.48568 (15)	0.09976 (5)	0.0193 (3)
H19A	0.6274	0.4395	0.0683	0.023*
C20	0.74986 (16)	0.58645 (16)	0.10501 (6)	0.0262 (3)
H20A	0.7281	0.6517	0.0790	0.039*
H20B	0.8250	0.5380	0.1038	0.039*
H20C	0.7650	0.6332	0.1356	0.039*
C21	0.67544 (15)	0.37717 (16)	0.13955 (6)	0.0227 (3)
H21A	0.7493	0.3281	0.1371	0.034*
H21B	0.6059	0.3147	0.1357	0.034*
H21C	0.6927	0.4204	0.1708	0.034*
C22	0.02950 (16)	−0.12061 (16)	0.16644 (5)	0.0224 (3)
H22A	−0.0588	−0.1475	0.1593	0.027*
H22B	0.0808	−0.2026	0.1740	0.027*
C23	0.18209 (15)	0.02413 (15)	0.22580 (5)	0.0196 (3)
C24	0.29008 (16)	−0.04544 (17)	0.22172 (6)	0.0227 (3)
H24A	0.2821	−0.1297	0.2061	0.027*
C25	0.40981 (16)	0.01206 (17)	0.24111 (6)	0.0258 (3)
H25A	0.4816	−0.0355	0.2391	0.031*
C26	0.42321 (16)	0.13885 (18)	0.26334 (6)	0.0275 (4)
H26A	0.5032	0.1768	0.2761	0.033*
C27	0.31547 (17)	0.20828 (17)	0.26626 (6)	0.0275 (4)
H27A	0.3236	0.2940	0.2808	0.033*
C28	0.19685 (15)	0.15264 (16)	0.24802 (6)	0.0231 (3)
H28A	0.1258	0.2009	0.2505	0.028*
C29	−0.03703 (14)	0.00563 (15)	0.22995 (5)	0.0183 (3)
C30	−0.14889 (15)	0.06584 (17)	0.20375 (6)	0.0234 (3)
H30A	−0.1623	0.0840	0.1708	0.028*
C31	−0.24132 (15)	0.09931 (17)	0.22671 (6)	0.0252 (3)
H31A	−0.3170	0.1389	0.2090	0.030*
C32	−0.22099 (15)	0.07391 (16)	0.27591 (6)	0.0238 (3)
H32A	−0.2830	0.0962	0.2912	0.029*
C33	−0.10801 (15)	0.01518 (15)	0.30232 (6)	0.0222 (3)
H33A	−0.0938	−0.0006	0.3354	0.027*
C34	−0.01663 (15)	−0.01996 (15)	0.27969 (6)	0.0207 (3)
H34A	0.0585	−0.0606	0.2974	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02348 (8)	0.03478 (9)	0.01983 (7)	0.00250 (7)	0.00969 (6)	0.00190 (7)
S1	0.0432 (3)	0.01778 (18)	0.0276 (2)	0.00609 (17)	0.01949 (19)	0.00226 (15)
N1	0.0210 (6)	0.0184 (6)	0.0148 (5)	0.0036 (5)	0.0069 (5)	0.0005 (5)
N2	0.0205 (6)	0.0183 (6)	0.0200 (6)	0.0040 (5)	0.0064 (5)	0.0002 (5)
N3	0.0237 (6)	0.0183 (6)	0.0171 (6)	0.0025 (5)	0.0079 (5)	0.0003 (5)
N4	0.0200 (6)	0.0272 (7)	0.0181 (6)	−0.0008 (5)	0.0076 (5)	−0.0047 (5)
N5	0.0207 (6)	0.0199 (6)	0.0161 (5)	−0.0001 (5)	0.0066 (5)	−0.0017 (5)
C1	0.0221 (7)	0.0199 (7)	0.0168 (7)	0.0015 (6)	0.0067 (6)	−0.0008 (5)
C2	0.0165 (7)	0.0195 (7)	0.0168 (6)	0.0023 (5)	0.0044 (6)	−0.0018 (5)
C3	0.0225 (7)	0.0192 (7)	0.0156 (6)	0.0008 (6)	0.0052 (6)	0.0002 (5)
C4	0.0188 (7)	0.0173 (7)	0.0144 (6)	−0.0004 (5)	0.0037 (5)	−0.0014 (5)
C5	0.0251 (8)	0.0165 (7)	0.0160 (6)	0.0018 (6)	0.0053 (6)	−0.0006 (5)
C6	0.0208 (7)	0.0178 (7)	0.0193 (7)	0.0025 (6)	0.0051 (6)	−0.0032 (5)
C7	0.0209 (7)	0.0231 (7)	0.0146 (6)	−0.0007 (6)	0.0056 (6)	−0.0030 (5)
C8	0.0215 (7)	0.0212 (7)	0.0170 (7)	0.0027 (6)	0.0037 (6)	0.0018 (6)
C9	0.0197 (7)	0.0206 (7)	0.0175 (7)	0.0033 (6)	0.0040 (6)	−0.0008 (5)
C10	0.0209 (7)	0.0191 (7)	0.0178 (7)	0.0040 (6)	0.0036 (6)	0.0001 (5)
C11	0.0206 (7)	0.0151 (6)	0.0191 (7)	0.0051 (5)	0.0062 (6)	0.0004 (5)
C12	0.0242 (7)	0.0200 (7)	0.0151 (6)	0.0052 (6)	0.0028 (6)	0.0019 (5)
C13	0.0256 (8)	0.0210 (7)	0.0200 (7)	0.0043 (6)	0.0075 (6)	0.0048 (6)
C14	0.0222 (7)	0.0162 (7)	0.0212 (7)	0.0043 (5)	0.0061 (6)	0.0011 (5)
C15	0.0239 (8)	0.0240 (8)	0.0172 (7)	0.0031 (6)	0.0052 (6)	−0.0019 (6)
C16	0.0245 (8)	0.0220 (7)	0.0175 (7)	0.0024 (6)	0.0088 (6)	0.0013 (6)
C17	0.0220 (8)	0.0230 (8)	0.0317 (9)	0.0060 (6)	0.0059 (7)	0.0004 (7)
C18	0.0265 (8)	0.0180 (7)	0.0239 (8)	0.0008 (6)	0.0068 (6)	0.0011 (6)
C19	0.0242 (7)	0.0185 (7)	0.0163 (6)	−0.0004 (6)	0.0074 (6)	−0.0008 (5)
C20	0.0297 (9)	0.0208 (8)	0.0320 (9)	0.0001 (7)	0.0151 (7)	0.0009 (7)
C21	0.0251 (8)	0.0213 (7)	0.0213 (7)	0.0005 (6)	0.0059 (6)	0.0012 (6)
C22	0.0266 (8)	0.0234 (8)	0.0191 (7)	−0.0006 (6)	0.0099 (6)	−0.0016 (6)
C23	0.0218 (7)	0.0220 (8)	0.0164 (6)	0.0015 (6)	0.0074 (6)	0.0027 (5)
C24	0.0265 (8)	0.0241 (7)	0.0201 (7)	0.0031 (6)	0.0108 (6)	0.0007 (6)
C25	0.0218 (7)	0.0350 (9)	0.0231 (7)	0.0051 (7)	0.0106 (6)	0.0053 (7)
C26	0.0216 (8)	0.0352 (9)	0.0270 (8)	−0.0035 (7)	0.0088 (7)	0.0029 (7)
C27	0.0297 (9)	0.0237 (8)	0.0301 (9)	−0.0030 (7)	0.0101 (7)	0.0006 (7)
C28	0.0218 (7)	0.0215 (8)	0.0278 (8)	0.0019 (6)	0.0102 (7)	0.0033 (6)
C29	0.0196 (6)	0.0181 (7)	0.0179 (6)	0.0001 (6)	0.0062 (5)	−0.0011 (6)
C30	0.0260 (8)	0.0258 (8)	0.0171 (7)	0.0016 (7)	0.0038 (6)	0.0019 (6)
C31	0.0194 (7)	0.0266 (8)	0.0280 (8)	0.0029 (6)	0.0035 (6)	0.0025 (7)
C32	0.0200 (7)	0.0243 (8)	0.0299 (8)	0.0005 (6)	0.0116 (6)	−0.0030 (7)
C33	0.0254 (8)	0.0246 (8)	0.0182 (7)	−0.0008 (6)	0.0087 (6)	0.0004 (6)
C34	0.0203 (7)	0.0231 (8)	0.0180 (7)	0.0030 (6)	0.0042 (6)	0.0020 (6)

Geometric parameters (Å, º) top

Br1—C7	1.8925 (16)	C17—H17A	0.96
S1—C1	1.6688 (15)	C17—H17B	0.96
N1—C2	1.3800 (19)	C17—H17C	0.96
N1—N5	1.3879 (18)	C18—C19	1.535 (2)
N1—C1	1.3907 (19)	C18—H18A	0.97
N2—C2	1.2968 (19)	C18—H18B	0.97
N2—N3	1.3818 (18)	C19—C20	1.522 (2)
N3—C1	1.354 (2)	C19—C21	1.526 (2)
N3—C22	1.466 (2)	C19—H19A	0.98
N4—C23	1.404 (2)	C20—H20A	0.96
N4—C29	1.422 (2)	C20—H20B	0.96
N4—C22	1.4399 (19)	C20—H20C	0.96
N5—C3	1.2821 (19)	C21—H21A	0.96
C2—C10	1.497 (2)	C21—H21B	0.96
C3—C4	1.456 (2)	C21—H21C	0.96
C3—H3A	0.93	C22—H22A	0.97
C4—C5	1.395 (2)	C22—H22B	0.97
C4—C9	1.408 (2)	C23—C28	1.398 (2)
C5—C6	1.383 (2)	C23—C24	1.398 (2)
C5—H5A	0.93	C24—C25	1.396 (2)
C6—C7	1.384 (2)	C24—H24A	0.93
C6—H6A	0.93	C25—C26	1.383 (2)
C7—C8	1.388 (2)	C25—H25A	0.93
C8—C9	1.378 (2)	C26—C27	1.385 (2)
C8—H8A	0.93	C26—H26A	0.93
C9—H9A	0.93	C27—C28	1.374 (2)
C10—C11	1.519 (2)	C27—H27A	0.93
C10—C17	1.531 (2)	C28—H28A	0.93
C10—H10A	0.98	C29—C30	1.381 (2)
C11—C12	1.392 (2)	C29—C34	1.402 (2)
C11—C16	1.392 (2)	C30—C31	1.390 (2)
C12—C13	1.386 (2)	C30—H30A	0.93
C12—H12A	0.93	C31—C32	1.386 (2)
C13—C14	1.397 (2)	C31—H31A	0.93
C13—H13A	0.93	C32—C33	1.386 (2)
C14—C15	1.395 (2)	C32—H32A	0.93
C14—C18	1.508 (2)	C33—C34	1.378 (2)
C15—C16	1.387 (2)	C33—H33A	0.93
C15—H15A	0.93	C34—H34A	0.93
C16—H16A	0.93

C2—N1—N5	118.83 (12)	H17B—C17—H17C	109.5
C2—N1—C1	108.47 (13)	C14—C18—C19	114.99 (13)
N5—N1—C1	132.69 (12)	C14—C18—H18A	108.5
C2—N2—N3	104.23 (12)	C19—C18—H18A	108.5
C1—N3—N2	113.84 (12)	C14—C18—H18B	108.5
C1—N3—C22	125.69 (13)	C19—C18—H18B	108.5
N2—N3—C22	120.35 (12)	H18A—C18—H18B	107.5
C23—N4—C29	119.80 (12)	C20—C19—C21	110.56 (13)
C23—N4—C22	121.01 (13)	C20—C19—C18	110.48 (12)
C29—N4—C22	119.14 (13)	C21—C19—C18	111.82 (13)
C3—N5—N1	118.00 (12)	C20—C19—H19A	107.9
N3—C1—N1	102.21 (12)	C21—C19—H19A	107.9
N3—C1—S1	127.43 (12)	C18—C19—H19A	107.9
N1—C1—S1	130.26 (12)	C19—C20—H20A	109.5
N2—C2—N1	111.21 (13)	C19—C20—H20B	109.5
N2—C2—C10	125.62 (13)	H20A—C20—H20B	109.5
N1—C2—C10	123.10 (13)	C19—C20—H20C	109.5
N5—C3—C4	119.71 (13)	H20A—C20—H20C	109.5
N5—C3—H3A	120.1	H20B—C20—H20C	109.5
C4—C3—H3A	120.1	C19—C21—H21A	109.5
C5—C4—C9	118.73 (14)	C19—C21—H21B	109.5
C5—C4—C3	118.76 (13)	H21A—C21—H21B	109.5
C9—C4—C3	122.39 (14)	C19—C21—H21C	109.5
C6—C5—C4	121.49 (14)	H21A—C21—H21C	109.5
C6—C5—H5A	119.3	H21B—C21—H21C	109.5
C4—C5—H5A	119.3	N4—C22—N3	112.04 (13)
C5—C6—C7	118.48 (14)	N4—C22—H22A	109.2
C5—C6—H6A	120.8	N3—C22—H22A	109.2
C7—C6—H6A	120.8	N4—C22—H22B	109.2
C6—C7—C8	121.48 (15)	N3—C22—H22B	109.2
C6—C7—Br1	119.31 (12)	H22A—C22—H22B	107.9
C8—C7—Br1	119.20 (12)	C28—C23—C24	118.75 (15)
C9—C8—C7	119.73 (14)	C28—C23—N4	119.42 (14)
C9—C8—H8A	120.1	C24—C23—N4	121.83 (14)
C7—C8—H8A	120.1	C25—C24—C23	119.77 (15)
C8—C9—C4	120.05 (14)	C25—C24—H24A	120.1
C8—C9—H9A	120.0	C23—C24—H24A	120.1
C4—C9—H9A	120.0	C26—C25—C24	120.90 (16)
C2—C10—C11	111.34 (12)	C26—C25—H25A	119.5
C2—C10—C17	110.33 (13)	C24—C25—H25A	119.5
C11—C10—C17	110.39 (12)	C25—C26—C27	118.88 (16)
C2—C10—H10A	108.2	C25—C26—H26A	120.6
C11—C10—H10A	108.2	C27—C26—H26A	120.6
C17—C10—H10A	108.2	C28—C27—C26	121.13 (16)
C12—C11—C16	118.23 (14)	C28—C27—H27A	119.4
C12—C11—C10	120.12 (13)	C26—C27—H27A	119.4
C16—C11—C10	121.44 (14)	C27—C28—C23	120.54 (15)
C13—C12—C11	120.94 (14)	C27—C28—H28A	119.7
C13—C12—H12A	119.5	C23—C28—H28A	119.7
C11—C12—H12A	119.5	C30—C29—C34	119.83 (14)
C12—C13—C14	121.13 (15)	C30—C29—N4	121.92 (14)
C12—C13—H13A	119.4	C34—C29—N4	118.25 (13)
C14—C13—H13A	119.4	C29—C30—C31	119.85 (14)
C15—C14—C13	117.60 (15)	C29—C30—H30A	120.1
C15—C14—C18	121.65 (14)	C31—C30—H30A	120.1
C13—C14—C18	120.75 (14)	C32—C31—C30	120.24 (15)
C16—C15—C14	121.29 (14)	C32—C31—H31A	119.9
C16—C15—H15A	119.4	C30—C31—H31A	119.9
C14—C15—H15A	119.4	C31—C32—C33	119.87 (15)
C15—C16—C11	120.77 (15)	C31—C32—H32A	120.1
C15—C16—H16A	119.6	C33—C32—H32A	120.1
C11—C16—H16A	119.6	C34—C33—C32	120.24 (15)
C10—C17—H17A	109.5	C34—C33—H33A	119.9
C10—C17—H17B	109.5	C32—C33—H33A	119.9
H17A—C17—H17B	109.5	C33—C34—C29	119.96 (14)
C10—C17—H17C	109.5	C33—C34—H34A	120.0
H17A—C17—H17C	109.5	C29—C34—H34A	120.0

C2—N2—N3—C1	−0.72 (16)	C11—C12—C13—C14	−0.1 (2)
C2—N2—N3—C22	175.64 (13)	C12—C13—C14—C15	1.3 (2)
C2—N1—N5—C3	159.63 (14)	C12—C13—C14—C18	−178.97 (14)
C1—N1—N5—C3	−21.9 (2)	C13—C14—C15—C16	−1.0 (2)
N2—N3—C1—N1	1.58 (16)	C18—C14—C15—C16	179.34 (14)
C22—N3—C1—N1	−174.54 (13)	C14—C15—C16—C11	−0.6 (2)
N2—N3—C1—S1	−175.19 (11)	C12—C11—C16—C15	1.8 (2)
C22—N3—C1—S1	8.7 (2)	C10—C11—C16—C15	−173.02 (14)
C2—N1—C1—N3	−1.81 (15)	C15—C14—C18—C19	91.60 (18)
N5—N1—C1—N3	179.61 (14)	C13—C14—C18—C19	−88.07 (18)
C2—N1—C1—S1	174.83 (12)	C14—C18—C19—C20	171.34 (13)
N5—N1—C1—S1	−3.7 (3)	C14—C18—C19—C21	−65.06 (17)
N3—N2—C2—N1	−0.53 (15)	C23—N4—C22—N3	−58.20 (18)
N3—N2—C2—C10	−177.61 (13)	C29—N4—C22—N3	119.16 (15)
N5—N1—C2—N2	−179.65 (12)	C1—N3—C22—N4	134.71 (15)
C1—N1—C2—N2	1.54 (17)	N2—N3—C22—N4	−41.18 (18)
N5—N1—C2—C10	−2.5 (2)	C29—N4—C23—C28	−28.3 (2)
C1—N1—C2—C10	178.71 (13)	C22—N4—C23—C28	149.07 (15)
N1—N5—C3—C4	−175.35 (12)	C29—N4—C23—C24	152.09 (15)
N5—C3—C4—C5	173.71 (14)	C22—N4—C23—C24	−30.6 (2)
N5—C3—C4—C9	−2.3 (2)	C28—C23—C24—C25	2.1 (2)
C9—C4—C5—C6	2.0 (2)	N4—C23—C24—C25	−178.29 (14)
C3—C4—C5—C6	−174.15 (14)	C23—C24—C25—C26	−1.6 (2)
C4—C5—C6—C7	−1.0 (2)	C24—C25—C26—C27	0.2 (2)
C5—C6—C7—C8	−0.5 (2)	C25—C26—C27—C28	0.7 (3)
C5—C6—C7—Br1	178.70 (11)	C26—C27—C28—C23	−0.2 (3)
C6—C7—C8—C9	1.0 (2)	C24—C23—C28—C27	−1.2 (2)
Br1—C7—C8—C9	−178.16 (11)	N4—C23—C28—C27	179.18 (15)
C7—C8—C9—C4	−0.1 (2)	C23—N4—C29—C30	121.59 (16)
C5—C4—C9—C8	−1.4 (2)	C22—N4—C29—C30	−55.8 (2)
C3—C4—C9—C8	174.57 (14)	C23—N4—C29—C34	−58.07 (19)
N2—C2—C10—C11	103.74 (17)	C22—N4—C29—C34	124.55 (15)
N1—C2—C10—C11	−73.02 (18)	C34—C29—C30—C31	−0.7 (2)
N2—C2—C10—C17	−19.2 (2)	N4—C29—C30—C31	179.60 (14)
N1—C2—C10—C17	164.05 (13)	C29—C30—C31—C32	0.7 (2)
C2—C10—C11—C12	135.56 (14)	C30—C31—C32—C33	0.1 (2)
C17—C10—C11—C12	−101.54 (16)	C31—C32—C33—C34	−1.0 (2)
C2—C10—C11—C16	−49.71 (19)	C32—C33—C34—C29	1.0 (2)
C17—C10—C11—C16	73.20 (17)	C30—C29—C34—C33	−0.1 (2)
C16—C11—C12—C13	−1.5 (2)	N4—C29—C34—C33	179.55 (14)
C10—C11—C12—C13	173.45 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S1	0.93	2.52	3.217 (2)	132
C22—H22B···S1	0.97	2.80	3.232 (2)	108
C6—H6A···Cg1ⁱ	0.93	2.81	3.717 (2)	165
C21—H21C···Cg2ⁱⁱ	0.96	2.89	3.829 (2)	168

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

Experimental details

Crystal data
Chemical formula	C₃₄H₃₄BrN₅S
M_r	624.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.9672 (1), 9.7833 (1), 28.6210 (3)
β (°)	105.966 (1)
V (Å³)	2952.44 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.35 × 0.31 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.623, 0.684
No. of measured, independent and observed [I > 2σ(I)] reflections	55283, 13248, 7914
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.815

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.098, 1.02
No. of reflections	13248
No. of parameters	372
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.57

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S1	0.93	2.52	3.217 (2)	132
C22—H22B···S1	0.97	2.80	3.232 (2)	108
C6—H6A···Cg1ⁱ	0.93	2.81	3.717 (2)	165
C21—H21C···Cg2ⁱⁱ	0.96	2.89	3.829 (2)	168

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dave, T. K., Purohit, D. H., Akbari, J. D. & Joshi, H. S. (2007). Indian J. Heterocycl. Chem. 46B, 352–356. CAS Google Scholar
Kalluraya, B., Isloor, A. M., Chimbalkar, R. M. & Shenoy, S. (2001). Indian J. Heterocycl. Chem. 10, 239–240. CAS Google Scholar
Kalluraya, B., Lingappa, B. & Rai, N. S. (2007). Phosphorus Sulfur Silicon Relat. Elem. 182, 1393–1401. Web of Science CrossRef CAS Google Scholar
Kalluraya, B. & Rai, G. (2003). Synth. Commun. 33, 3583–3589. Web of Science CrossRef Google Scholar
Kalluraya, B., Rai, G., Rai, S. & Shenoy, S. (2004). Indian J. Heterocycl. Chem. 14, 127–130. CAS Google Scholar
Kane, J. M., Baron, B. M., Dudley, M. W., Sorensen, S. M., Staeger, M. A. & Miller, F. P. (1990). J. Med. Chem. 33, 2772–2777. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 64| Part 6| June 2008| Pages o1001-o1002

doi:10.1107/S1600536808012713

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

4-(4-Bromo­benzyl­­idene­amino)-1-(di­phenyl­amino­meth­yl)-3-[1-(4-iso­butyl­phen­yl)eth­yl]-1H-1,2,4-triazole-5(4H)-thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-(4-Bromobenzylideneamino)-1-(diphenylaminomethyl)-3-[1-(4-isobutylphenyl)ethyl]-1H-1,2,4-triazole-5(4H)-thione