3-Benzyl-7-(2,4-dichloro­phen­yl)-4H-1,3,4-thia­diazolo[2,3-c][1,2,4]triazin-4-one

Fun, H.-K.; Arshad, S.; Sarojini, B.K.; Imran, U.A.; Krishna, B.G.

doi:10.1107/S1600536812021253

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1736-o1737

doi:10.1107/S1600536812021253

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3-Benzyl-7-(2,4-dichlorophenyl)-4H-1,3,4-thiadiazolo[2,3-c][1,2,4]triazin-4-one

Hoong-Kun Fun,^a ^*‡ Suhana Arshad,^a B. K. Sarojini,^b U. A. Imran ^b and B.G. Krishna ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, P. A. College of Engineering, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 24 April 2012; accepted 10 May 2012; online 16 May 2012)

In the title compound, C₁₇H₁₀Cl₂N₄OS, the phenyl ring and the H atoms attached to the adjacent C atom are disordered over two positions, with refined site occupancies of 0.509 (8) and 0.491 (8). The planar 4H-1,3,4-thiadiazolo[2,3-c][1,2,4]triazine ring system [maximum deviation = 0.048 (3) Å] forms dihedral angles of 76.9 (5), 74.9 (5) and 9.88 (12)°, respectively, with the major and minor parts of the disordered phenyl ring and with the dichloro-substituted benzene ring. In the crystal, pairs of C—H⋯O hydrogen bonds link the molecules, forming inversion dimers with an R₂²(18) graph-set motif. A short S⋯N contact of 2.801 (3) Å is observed between the dimers.

Related literature

For applications of thiadiazole derivatives, see: Kurtzer (1965 ); Sandstrom (1968 ); Eue & Tietz (1970 ); Holla et al. (1988 , 1998 ). For a related structure, see: Zhang et al. (2011 ); Fun et al. (2011 ); Ma & Yang (2008 ); Yu et al. (2007 ); Jia et al. (2011 ). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₀Cl₂N₄OS
M_r = 389.25
Triclinic, $[P \overline 1]$
a = 4.4961 (1) Å
b = 13.4412 (5) Å
c = 14.4588 (5) Å
α = 70.620 (2)°
β = 85.956 (2)°
γ = 83.063 (2)°
V = 817.81 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.54 mm⁻¹
T = 100 K
0.21 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.894, T_max = 0.955
8906 measured reflections
4086 independent reflections
2479 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.129
S = 1.04
4086 reflections
281 parameters
180 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	0.95	2.36	3.226 (5)	151
Symmetry code: (i) -x+1, -y+2, -z+2.

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: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021253/is5127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021253/is5127Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021253/is5127Isup3.cml

checkCIF report

Comment top

Several thiadiazoles find important application in the field of medicine, agriculture and industry (Kurtzer, 1965; Sandstrom, 1968). Thiadiazoles were also used as effective herbicides and fungicides (Eue & Tietz, 1970). The antibacterial activity of some of the thiadiazolotriazinone derivatives were reported (Holla et al., 1998). The presence of substituents like aryloxymethyl and anilinomethyl on thiadiazole moiety were known to enhance the biological activities (Holla et al., 1988). The crystal structures of some of the thiadiazole derivatives have been reported (Zhang et al., 2011; Fun et al., 2011; Ma & Yang, 2008). The present work describes the synthesis and crystal structure of the title compound (C₁₇H₁₀Cl₂N₄OS), 3-benzyl-7-(2,4-dichlorophenyl)-4H -[1,3,4]thiadiazolo[2,3-c][1,2,4]triazin-4-one. The compound was prepared by the reaction of 4-amino-6-benzyl-3-mercapto-1,2,4-triazin- 5(4H)-one with 2,4 dichlorobenzoic acid.

The molecular structure is shown in Fig. 1. The benzene ring and the hydrogen atoms which are attached to atom C11 are disordered over two positions with refined site-occupancies of 0.509 (8): 0.491 (8) ratio. Bond lengths and angles are within normal ranges. The 4H-[1,3,4]thiadiazolo [2,3-c][1,2,4]triazine ring (S1/N1/N2/N3/N4/C7–C10; maximum deviation = 0.048 (3) Å at atom C9) forms dihedral angles of 76.9 (5), 74.9 (5) and 9.88 (12)° with the major and minor parts of the disordered benzene ring (C12–C17 & C12X–C17X) and the dichloro-substituted benzene ring (C1–C6), respectively.

In the crystal packing (Fig. 2), two neighbouring molecules are linked by intermolecular C2—H2A···O1 hydrogen bonds (Table 1) into inversion dimers, forming R²₂(18) graph-set motifs (Bernstein et al., 1995). A short S1···N3 contact [2.801 (3) Å, symmetry code: -x,1 - y,2 - z] is observed between the dimers and comparable with those short contacts of the previously reported structures (Yu et al., 2007; Jia et al., 2011).

Related literature top

For applications of thiadiazole derivatives, see: Kurtzer (1965); Sandstrom (1968); Eue & Tietz (1970); Holla et al. (1988, 1998). For a related structure, see: Zhang et al. (2011); Fun et al. (2011); Ma & Yang (2008); Yu et al. (2007); Jia et al. (2011). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986). for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 4-amino-6-benzyl-3-mercapto-1,2,4-triazin-5(4H)-one (2.34 g, 0.01 mol), 2,4-dichlorobenzoic acid (1.91 g, 0.01 mol) and phosphorus oxychloride (10 ml) was refluxed on a water bath for about 5 h. Excess of phosphorus oxychloride was removed under reduced pressure. The reaction mixture was cooled and poured onto crushed ice. The resulting solid product was filtered, washed with sodium bicarbonate solution (2%), followed by distilled water. It was dried and recrystallized from aqueous dioxane. The single crystals were grown by slow evaporation from a mixture of ethanol and dichloromethane. (1:1) (M.p. = 473–475 K).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. All disordered components are shown.
	Fig. 2. A packing diagram of the title compound viewed along the a axis. Dashed lines represent the intermolecular hydrogen bonds. Only major disordered component is shown.

3-Benzyl-7-(2,4-dichlorophenyl)-4H-1,3,4- thiadiazolo[2,3-c][1,2,4]triazin-4-one top

Crystal data top

C₁₇H₁₀Cl₂N₄OS	Z = 2
M_r = 389.25	F(000) = 396
Triclinic, P1	D_x = 1.581 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.4961 (1) Å	Cell parameters from 5482 reflections
b = 13.4412 (5) Å	θ = 2.5–31.5°
c = 14.4588 (5) Å	µ = 0.54 mm⁻¹
α = 70.620 (2)°	T = 100 K
β = 85.956 (2)°	Block, yellow
γ = 83.063 (2)°	0.21 × 0.10 × 0.09 mm
V = 817.81 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4086 independent reflections
Radiation source: fine-focus sealed tube	2479 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
T_min = 0.894, T_max = 0.955	k = −18→18
8906 measured reflections	l = −18→19

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0449P)² + 0.2058P] where P = (F_o² + 2F_c²)/3
4086 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.42 e Å⁻³
180 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₇H₁₀Cl₂N₄OS	γ = 83.063 (2)°
M_r = 389.25	V = 817.81 (5) Å³
Triclinic, P1	Z = 2
a = 4.4961 (1) Å	Mo Kα radiation
b = 13.4412 (5) Å	µ = 0.54 mm⁻¹
c = 14.4588 (5) Å	T = 100 K
α = 70.620 (2)°	0.21 × 0.10 × 0.09 mm
β = 85.956 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4086 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2479 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.955	R_int = 0.053
8906 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	180 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.04	Δρ_max = 0.42 e Å⁻³
4086 reflections	Δρ_min = −0.38 e Å⁻³
281 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	Occ. (<1)
Cl1	−0.1885 (2)	1.03193 (7)	1.30609 (7)	0.0514 (3)
Cl2	−0.2647 (2)	0.66171 (7)	1.25574 (6)	0.0410 (3)
S1	0.00839 (17)	0.62886 (7)	1.07446 (5)	0.0301 (2)
O1	0.7716 (5)	0.79090 (18)	0.84041 (16)	0.0380 (6)
N1	0.3542 (6)	0.7790 (2)	0.99367 (18)	0.0301 (6)
N2	0.3951 (5)	0.7091 (2)	0.94181 (18)	0.0284 (6)
N3	0.2316 (5)	0.5525 (2)	0.92944 (17)	0.0321 (7)
N4	0.4208 (5)	0.5638 (2)	0.84780 (18)	0.0330 (7)
C1	0.1722 (7)	0.9123 (3)	1.1014 (2)	0.0338 (8)
H1A	0.3000	0.9339	1.0447	0.041*
C2	0.0985 (8)	0.9801 (3)	1.1546 (2)	0.0376 (8)
H2A	0.1744	1.0473	1.1351	0.045*
C3	−0.0885 (7)	0.9488 (3)	1.2373 (2)	0.0360 (8)
C4	−0.1976 (7)	0.8511 (3)	1.2661 (2)	0.0354 (8)
H4A	−0.3251	0.8301	1.3230	0.043*
C5	−0.1205 (7)	0.7840 (3)	1.2119 (2)	0.0296 (7)
C6	0.0653 (7)	0.8122 (3)	1.1278 (2)	0.0292 (7)
C7	0.1560 (7)	0.7466 (3)	1.0647 (2)	0.0281 (7)
C8	0.2259 (7)	0.6250 (3)	0.9714 (2)	0.0294 (7)
C9	0.6039 (7)	0.7215 (3)	0.8630 (2)	0.0309 (8)
C10	0.5922 (7)	0.6403 (3)	0.8173 (2)	0.0313 (8)
C11	0.7890 (7)	0.6472 (3)	0.7261 (2)	0.0371 (9)
H11A	0.9216	0.5801	0.7374	0.045*	0.509 (8)
H11B	0.9176	0.7053	0.7140	0.045*	0.509 (8)
H11C	0.9466	0.6944	0.7210	0.045*	0.491 (8)
H11D	0.8881	0.5759	0.7305	0.045*	0.491 (8)
C12	0.600 (6)	0.6676 (16)	0.6331 (18)	0.020 (3)	0.509 (8)
C13	0.4824 (18)	0.7651 (7)	0.5769 (5)	0.0307 (18)	0.509 (8)
H13A	0.5246	0.8266	0.5899	0.037*	0.509 (8)
C14	0.302 (4)	0.7744 (17)	0.5012 (10)	0.044 (3)	0.509 (8)
H14A	0.2146	0.8423	0.4631	0.053*	0.509 (8)
C15	0.248 (3)	0.6858 (12)	0.4802 (8)	0.049 (3)	0.509 (8)
H15A	0.1266	0.6927	0.4268	0.059*	0.509 (8)
C16	0.3718 (17)	0.5854 (7)	0.5380 (5)	0.042 (2)	0.509 (8)
H16A	0.3364	0.5239	0.5237	0.051*	0.509 (8)
C17	0.546 (2)	0.5769 (7)	0.6159 (7)	0.034 (2)	0.509 (8)
H17A	0.6267	0.5093	0.6569	0.041*	0.509 (8)
C12X	0.611 (7)	0.6874 (18)	0.6421 (19)	0.023 (3)	0.491 (8)
C13X	0.5639 (18)	0.7976 (7)	0.5985 (6)	0.0300 (18)	0.491 (8)
H13B	0.6560	0.8415	0.6253	0.036*	0.491 (8)
C14X	0.3859 (17)	0.8449 (7)	0.5171 (5)	0.041 (2)	0.491 (8)
H14B	0.3532	0.9199	0.4898	0.050*	0.491 (8)
C15X	0.256 (4)	0.7806 (18)	0.4761 (10)	0.042 (3)	0.491 (8)
H15B	0.1343	0.8127	0.4208	0.050*	0.491 (8)
C16X	0.302 (3)	0.6708 (13)	0.5142 (7)	0.041 (2)	0.491 (8)
H16B	0.2120	0.6277	0.4861	0.049*	0.491 (8)
C17X	0.483 (2)	0.6257 (8)	0.5948 (7)	0.033 (2)	0.491 (8)
H17B	0.5238	0.5507	0.6193	0.040*	0.491 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0638 (7)	0.0300 (5)	0.0509 (6)	0.0054 (5)	0.0255 (5)	−0.0094 (4)
Cl2	0.0471 (5)	0.0458 (6)	0.0308 (5)	−0.0175 (4)	0.0167 (4)	−0.0126 (4)
S1	0.0230 (4)	0.0477 (5)	0.0195 (4)	−0.0078 (4)	0.0029 (3)	−0.0101 (4)
O1	0.0324 (13)	0.0363 (14)	0.0368 (13)	−0.0029 (11)	0.0121 (10)	−0.0035 (11)
N1	0.0250 (14)	0.0336 (16)	0.0261 (14)	0.0025 (12)	0.0024 (11)	−0.0049 (12)
N2	0.0209 (13)	0.0383 (16)	0.0228 (13)	0.0010 (12)	0.0022 (11)	−0.0076 (12)
N3	0.0220 (14)	0.059 (2)	0.0178 (13)	−0.0098 (14)	0.0029 (10)	−0.0146 (13)
N4	0.0189 (13)	0.065 (2)	0.0189 (13)	−0.0113 (14)	0.0041 (10)	−0.0174 (13)
C1	0.0279 (18)	0.0290 (19)	0.0327 (18)	0.0058 (15)	0.0077 (14)	0.0008 (15)
C2	0.038 (2)	0.0248 (18)	0.0365 (19)	0.0046 (16)	0.0101 (16)	0.0027 (15)
C3	0.0323 (19)	0.0298 (19)	0.038 (2)	0.0105 (15)	0.0043 (15)	−0.0056 (15)
C4	0.0338 (19)	0.034 (2)	0.0289 (18)	0.0028 (16)	0.0108 (14)	−0.0020 (15)
C5	0.0270 (17)	0.0313 (18)	0.0253 (16)	−0.0021 (15)	0.0027 (13)	−0.0031 (14)
C6	0.0231 (17)	0.0342 (19)	0.0235 (16)	0.0048 (14)	0.0010 (13)	−0.0036 (14)
C7	0.0210 (16)	0.0343 (19)	0.0219 (16)	0.0001 (14)	−0.0002 (12)	−0.0007 (13)
C8	0.0194 (16)	0.050 (2)	0.0169 (15)	−0.0035 (15)	−0.0006 (12)	−0.0079 (14)
C9	0.0232 (17)	0.040 (2)	0.0215 (16)	0.0038 (16)	0.0003 (13)	−0.0014 (14)
C10	0.0175 (15)	0.054 (2)	0.0195 (15)	−0.0005 (16)	−0.0001 (12)	−0.0087 (15)
C11	0.0227 (17)	0.064 (3)	0.0236 (17)	−0.0066 (17)	0.0083 (13)	−0.0135 (17)
C12	0.019 (5)	0.034 (7)	0.011 (4)	0.005 (5)	0.002 (3)	−0.013 (4)
C13	0.038 (4)	0.035 (4)	0.018 (3)	0.000 (3)	0.008 (3)	−0.010 (3)
C14	0.033 (6)	0.064 (5)	0.020 (6)	0.013 (5)	−0.002 (4)	0.000 (6)
C15	0.033 (5)	0.080 (7)	0.025 (5)	−0.002 (5)	−0.005 (4)	−0.007 (5)
C16	0.048 (4)	0.058 (5)	0.029 (4)	−0.012 (4)	0.013 (3)	−0.027 (4)
C17	0.041 (5)	0.035 (5)	0.024 (4)	−0.004 (4)	0.007 (3)	−0.006 (4)
C12X	0.019 (4)	0.035 (7)	0.016 (6)	−0.008 (5)	0.008 (4)	−0.011 (4)
C13X	0.028 (4)	0.036 (4)	0.022 (4)	0.003 (3)	0.006 (3)	−0.008 (3)
C14X	0.039 (4)	0.051 (5)	0.022 (3)	0.005 (4)	0.009 (3)	0.000 (3)
C15X	0.019 (5)	0.083 (7)	0.014 (6)	0.009 (5)	0.001 (4)	−0.010 (6)
C16X	0.024 (5)	0.074 (6)	0.023 (5)	−0.004 (5)	0.003 (4)	−0.015 (5)
C17X	0.039 (5)	0.042 (5)	0.019 (4)	−0.005 (4)	0.011 (3)	−0.012 (4)

Geometric parameters (Å, º) top

Cl1—C3	1.730 (4)	C11—H11A	0.9900
Cl2—C5	1.741 (3)	C11—H11B	0.9900
S1—C8	1.736 (3)	C11—H11C	0.9900
S1—C7	1.749 (3)	C11—H11D	0.9900
O1—C9	1.216 (4)	C12—C13	1.36 (2)
N1—C7	1.306 (4)	C12—C17	1.375 (18)
N1—N2	1.373 (4)	C13—C14	1.370 (14)
N2—C8	1.371 (4)	C13—H13A	0.9500
N2—C9	1.403 (4)	C14—C15	1.37 (3)
N3—C8	1.305 (4)	C14—H14A	0.9500
N3—N4	1.382 (3)	C15—C16	1.402 (16)
N4—C10	1.299 (4)	C15—H15A	0.9500
C1—C2	1.374 (5)	C16—C17	1.382 (12)
C1—C6	1.406 (4)	C16—H16A	0.9500
C1—H1A	0.9500	C17—H17A	0.9500
C2—C3	1.387 (4)	C12X—C13X	1.40 (2)
C2—H2A	0.9500	C12X—C17X	1.425 (19)
C3—C4	1.379 (5)	C13X—C14X	1.395 (10)
C4—C5	1.380 (4)	C13X—H13B	0.9500
C4—H4A	0.9500	C14X—C15X	1.40 (2)
C5—C6	1.395 (4)	C14X—H14B	0.9500
C6—C7	1.474 (4)	C15X—C16X	1.39 (3)
C9—C10	1.458 (5)	C15X—H15B	0.9500
C10—C11	1.518 (4)	C16X—C17X	1.391 (14)
C11—C12X	1.42 (3)	C16X—H16B	0.9500
C11—C12	1.57 (2)	C17X—H17B	0.9500

C8—S1—C7	88.09 (16)	H11A—C11—H11B	107.9
C7—N1—N2	109.0 (3)	C12X—C11—H11C	109.8
C8—N2—N1	117.1 (2)	C10—C11—H11C	109.8
C8—N2—C9	121.1 (3)	C12X—C11—H11D	109.8
N1—N2—C9	121.9 (3)	C10—C11—H11D	109.8
C8—N3—N4	116.4 (3)	H11C—C11—H11D	108.2
C10—N4—N3	121.4 (3)	C13—C12—C17	121.7 (16)
C2—C1—C6	122.4 (3)	C13—C12—C11	124.0 (12)
C2—C1—H1A	118.8	C17—C12—C11	114.2 (16)
C6—C1—H1A	118.8	C12—C13—C14	119.8 (13)
C1—C2—C3	118.8 (3)	C12—C13—H13A	120.1
C1—C2—H2A	120.6	C14—C13—H13A	120.1
C3—C2—H2A	120.6	C13—C14—C15	120.3 (15)
C4—C3—C2	120.7 (3)	C13—C14—H14A	119.9
C4—C3—Cl1	118.9 (3)	C15—C14—H14A	119.9
C2—C3—Cl1	120.4 (3)	C14—C15—C16	119.7 (10)
C3—C4—C5	119.6 (3)	C14—C15—H15A	120.1
C3—C4—H4A	120.2	C16—C15—H15A	120.1
C5—C4—H4A	120.2	C17—C16—C15	119.4 (9)
C4—C5—C6	121.8 (3)	C17—C16—H16A	120.3
C4—C5—Cl2	115.9 (2)	C15—C16—H16A	120.3
C6—C5—Cl2	122.2 (3)	C12—C17—C16	119.1 (12)
C5—C6—C1	116.6 (3)	C12—C17—H17A	120.5
C5—C6—C7	125.7 (3)	C16—C17—H17A	120.5
C1—C6—C7	117.7 (3)	C13X—C12X—C11	117.8 (13)
N1—C7—C6	118.7 (3)	C13X—C12X—C17X	116.3 (19)
N1—C7—S1	116.4 (2)	C11—C12X—C17X	125.9 (17)
C6—C7—S1	124.9 (2)	C14X—C13X—C12X	122.0 (12)
N3—C8—N2	125.2 (3)	C14X—C13X—H13B	119.0
N3—C8—S1	125.4 (2)	C12X—C13X—H13B	119.0
N2—C8—S1	109.4 (2)	C13X—C14X—C15X	119.1 (10)
O1—C9—N2	121.9 (3)	C13X—C14X—H14B	120.4
O1—C9—C10	127.1 (3)	C15X—C14X—H14B	120.4
N2—C9—C10	111.0 (3)	C16X—C15X—C14X	121.5 (11)
N4—C10—C9	124.8 (3)	C16X—C15X—H15B	119.3
N4—C10—C11	117.6 (3)	C14X—C15X—H15B	119.3
C9—C10—C11	117.6 (3)	C15X—C16X—C17X	118.2 (13)
C12X—C11—C10	109.5 (13)	C15X—C16X—H16B	120.9
C10—C11—C12	112.3 (11)	C17X—C16X—H16B	120.9
C10—C11—H11A	109.2	C16X—C17X—C12X	122.7 (14)
C12—C11—H11A	109.2	C16X—C17X—H17B	118.7
C10—C11—H11B	109.2	C12X—C17X—H17B	118.7
C12—C11—H11B	109.2

C7—N1—N2—C8	1.3 (4)	N1—N2—C9—O1	4.5 (5)
C7—N1—N2—C9	−177.7 (3)	C8—N2—C9—C10	4.1 (4)
C8—N3—N4—C10	2.7 (4)	N1—N2—C9—C10	−177.0 (3)
C6—C1—C2—C3	−0.1 (5)	N3—N4—C10—C9	−0.7 (5)
C1—C2—C3—C4	0.4 (5)	N3—N4—C10—C11	−179.1 (3)
C1—C2—C3—Cl1	−179.7 (3)	O1—C9—C10—N4	175.7 (3)
C2—C3—C4—C5	−0.2 (5)	N2—C9—C10—N4	−2.7 (4)
Cl1—C3—C4—C5	179.8 (3)	O1—C9—C10—C11	−5.8 (5)
C3—C4—C5—C6	−0.2 (5)	N2—C9—C10—C11	175.7 (3)
C3—C4—C5—Cl2	178.9 (2)	N4—C10—C11—C12X	75.2 (9)
C4—C5—C6—C1	0.4 (5)	C9—C10—C11—C12X	−103.4 (9)
Cl2—C5—C6—C1	−178.6 (2)	N4—C10—C11—C12	62.9 (9)
C4—C5—C6—C7	−179.1 (3)	C9—C10—C11—C12	−115.7 (8)
Cl2—C5—C6—C7	1.9 (5)	C10—C11—C12—C13	84 (2)
C2—C1—C6—C5	−0.3 (5)	C10—C11—C12—C17	−92.4 (19)
C2—C1—C6—C7	179.3 (3)	C17—C12—C13—C14	0 (3)
N2—N1—C7—C6	−177.3 (3)	C11—C12—C13—C14	−175.2 (18)
N2—N1—C7—S1	0.6 (3)	C12—C13—C14—C15	−2 (3)
C5—C6—C7—N1	−173.5 (3)	C13—C14—C15—C16	1 (3)
C1—C6—C7—N1	7.0 (4)	C14—C15—C16—C17	0.4 (19)
C5—C6—C7—S1	8.8 (5)	C13—C12—C17—C16	1 (3)
C1—C6—C7—S1	−170.7 (2)	C11—C12—C17—C16	177.5 (13)
C8—S1—C7—N1	−1.7 (3)	C15—C16—C17—C12	−1.9 (19)
C8—S1—C7—C6	176.0 (3)	C10—C11—C12X—C13X	87 (2)
N4—N3—C8—N2	−1.2 (5)	C10—C11—C12X—C17X	−95 (2)
N4—N3—C8—S1	−180.0 (2)	C11—C12X—C13X—C14X	−178.3 (14)
N1—N2—C8—N3	178.5 (3)	C17X—C12X—C13X—C14X	4 (3)
C9—N2—C8—N3	−2.5 (5)	C12X—C13X—C14X—C15X	−1.6 (19)
N1—N2—C8—S1	−2.5 (3)	C13X—C14X—C15X—C16X	0 (2)
C9—N2—C8—S1	176.5 (2)	C14X—C15X—C16X—C17X	0 (2)
C7—S1—C8—N3	−178.9 (3)	C15X—C16X—C17X—C12X	3 (2)
C7—S1—C8—N2	2.2 (2)	C13X—C12X—C17X—C16X	−5 (3)
C8—N2—C9—O1	−174.4 (3)	C11—C12X—C17X—C16X	177.7 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.95	2.36	3.226 (5)	151

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀Cl₂N₄OS
M_r	389.25
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.4961 (1), 13.4412 (5), 14.4588 (5)
α, β, γ (°)	70.620 (2), 85.956 (2), 83.063 (2)
V (Å³)	817.81 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.54
Crystal size (mm)	0.21 × 0.10 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.894, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	8906, 4086, 2479
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.129, 1.04
No. of reflections	4086
No. of parameters	281
No. of restraints	180
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.38

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.95	2.36	3.226 (5)	151

Symmetry code: (i) −x+1, −y+2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and SA thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of Academic Staff Training Scheme (ASTS). BKS gratefully acknowledges the Department of Atomic Energy (DAE)/BRNS, Government of India, for providing financial assistance in the BRNS Project (grant No. 2011/34/20-BRNS/0846).

References

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Volume 68| Part 6| June 2012| Pages o1736-o1737

doi:10.1107/S1600536812021253

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

3-Benzyl-7-(2,4-di­chloro­phen­yl)-4H-1,3,4-thia­diazolo[2,3-c][1,2,4]triazin-4-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-Benzyl-7-(2,4-dichlorophenyl)-4H-1,3,4-thiadiazolo[2,3-c][1,2,4]triazin-4-one