3-Benzyl-7-(2,4-dichloro-phen-yl)-4H-1,3,4-thia-diazolo[2,3-c][1,2,4]triazin-4-one.

In the title compound, C(17)H(10)Cl(2)N(4)OS, 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-thia-diazolo[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 mol-ecules, forming inversion dimers with an R(2) (2)(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 = 389.25

Triclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.129

S = 1.04

4086 reflections

281 parameters

180 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.38 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: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021253/is5127sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812021253/is5127Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H10Cl2N4OS	Z = 2
Mr = 389.25	F(000) = 396
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0449P)2 + 0.2058P] where P = (Fo2 + 2Fc2)/3
4086 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.42 e Å−3
180 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) .