2-(4-Methyl-phen-yl)-5-[({[5-(4-methyl-phen-yl)-1,3,4-thia-diazol-2-yl]sulfan-yl}meth-yl)sulfan-yl]-1,3,4-thia-diazole.

In the title compound, C(19)H(16)N(4)S(4), the mol-ecules exhibit a butterfly conformation, where the thia-diazole and attached benzene rings in two wings are almost coplanar, with dihedral angles of 0.8 (3) and 0.9 (3)°, respectively, while the two thia-diazole rings form a dihedral angle of 46.3 (3)°.

Related literature

For the biological properties of 1,3,4-thia­diazole derivatives, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶); Carvalho et al. (2004 ▶). For the crystal structures of related compounds, see: Li et al. (2011 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C19H16N4S4

M = 428.60

Monoclinic,

a = 16.8944 (14) Å

b = 4.1959 (5) Å

c = 27.107 (2) Å

β = 96.084 (8)°

V = 1910.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 113 K

0.50 × 0.04 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.785, T max = 0.980

14969 measured reflections

4535 independent reflections

2927 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.142

S = 0.96

4535 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.60 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007520/cv5245sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007520/cv5245Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007520/cv5245Isup3.cml

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

C19H16N4S4	F(000) = 888
Mr = 428.60	Dx = 1.490 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5461 reflections
a = 16.8944 (14) Å	θ = 1.4–27.8°
b = 4.1959 (5) Å	µ = 0.51 mm−1
c = 27.107 (2) Å	T = 113 K
β = 96.084 (8)°	Prism, colourless
V = 1910.7 (3) Å3	0.50 × 0.04 × 0.04 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	4535 independent reflections
Radiation source: rotating anode	2927 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.094
Detector resolution: 14.22 pixels mm-1	θmax = 27.8°, θmin = 1.4°
φ and ω scans	h = −22→22
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −5→4
Tmin = 0.785, Tmax = 0.980	l = −35→31
14969 measured reflections

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3
4535 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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
S1	0.41711 (5)	0.77165 (19)	−0.01333 (3)	0.0266 (2)
S2	0.39123 (5)	1.1072 (2)	0.08165 (3)	0.0282 (2)
S3	0.26282 (5)	1.06832 (19)	0.15267 (3)	0.0270 (2)
S4	0.33462 (5)	1.07934 (19)	0.26002 (3)	0.0268 (2)
N1	0.26848 (16)	0.6479 (6)	−0.02748 (10)	0.0285 (6)
N2	0.27897 (16)	0.8187 (6)	0.01681 (10)	0.0288 (6)
N3	0.39960 (17)	1.3525 (6)	0.18983 (10)	0.0292 (6)
N4	0.44931 (16)	1.4137 (6)	0.23312 (10)	0.0289 (6)
C1	0.3546 (2)	−0.0838 (8)	−0.23078 (12)	0.0349 (8)
H1A	0.3223	−0.2782	−0.2313	0.052*
H1B	0.4101	−0.1403	−0.2341	0.052*
H1C	0.3343	0.0547	−0.2584	0.052*
C2	0.3500 (2)	0.0891 (7)	−0.18231 (12)	0.0263 (7)
C3	0.4179 (2)	0.2240 (8)	−0.15616 (12)	0.0296 (8)
H3	0.4680	0.2007	−0.1687	0.036*
C4	0.4135 (2)	0.3902 (7)	−0.11251 (12)	0.0283 (7)
H4	0.4602	0.4807	−0.0955	0.034*
C5	0.34068 (19)	0.4251 (7)	−0.09335 (11)	0.0237 (7)
C6	0.27246 (19)	0.2897 (7)	−0.11872 (12)	0.0268 (7)
H6	0.2225	0.3126	−0.1060	0.032*
C7	0.2776 (2)	0.1227 (7)	−0.16224 (12)	0.0275 (7)
H7	0.2309	0.0289	−0.1788	0.033*
C8	0.33463 (19)	0.6019 (7)	−0.04729 (11)	0.0242 (7)
C9	0.35275 (19)	0.8994 (7)	0.02832 (11)	0.0255 (7)
C10	0.2996 (2)	1.2661 (7)	0.10072 (12)	0.0277 (7)
H10A	0.3080	1.4939	0.1092	0.033*
H10B	0.2581	1.2551	0.0721	0.033*
C11	0.33781 (19)	1.1814 (7)	0.19861 (12)	0.0247 (7)
C12	0.42392 (18)	1.2861 (7)	0.27270 (12)	0.0258 (7)
C13	0.46511 (19)	1.3186 (7)	0.32295 (12)	0.0262 (7)
C14	0.43531 (19)	1.1764 (8)	0.36363 (12)	0.0278 (7)
H14	0.3872	1.0580	0.3591	0.033*
C15	0.4755 (2)	1.2068 (8)	0.41067 (12)	0.0292 (7)
H15	0.4540	1.1096	0.4380	0.035*
C16	0.54653 (19)	1.3758 (7)	0.41906 (12)	0.0285 (7)
C17	0.5753 (2)	1.5225 (8)	0.37799 (12)	0.0286 (7)
H17	0.6231	1.6434	0.3826	0.034*
C18	0.53548 (19)	1.4947 (8)	0.33077 (12)	0.0279 (7)
H18	0.5562	1.5961	0.3035	0.033*
C19	0.5928 (2)	1.3981 (9)	0.46959 (12)	0.0346 (8)
H19A	0.6398	1.2602	0.4708	0.052*
H19B	0.5590	1.3294	0.4949	0.052*
H19C	0.6096	1.6190	0.4760	0.052*

	U11	U22	U33	U12	U13	U23
S1	0.0174 (4)	0.0334 (5)	0.0289 (4)	−0.0015 (3)	0.0025 (3)	−0.0022 (4)
S2	0.0207 (4)	0.0359 (5)	0.0279 (4)	−0.0021 (3)	0.0019 (3)	−0.0029 (4)
S3	0.0204 (4)	0.0320 (5)	0.0285 (4)	−0.0002 (3)	0.0022 (3)	−0.0018 (3)
S4	0.0197 (4)	0.0329 (5)	0.0279 (4)	−0.0018 (3)	0.0022 (3)	0.0007 (3)
N1	0.0230 (15)	0.0343 (16)	0.0279 (14)	0.0008 (12)	0.0014 (12)	−0.0048 (12)
N2	0.0242 (15)	0.0342 (16)	0.0282 (14)	0.0000 (12)	0.0035 (12)	−0.0044 (12)
N3	0.0228 (15)	0.0352 (16)	0.0296 (14)	−0.0016 (12)	0.0026 (12)	0.0011 (12)
N4	0.0211 (15)	0.0357 (16)	0.0297 (15)	−0.0025 (12)	0.0013 (12)	0.0020 (12)
C1	0.034 (2)	0.037 (2)	0.0336 (19)	0.0041 (16)	0.0044 (16)	−0.0033 (16)
C2	0.0266 (18)	0.0262 (17)	0.0261 (16)	0.0032 (14)	0.0024 (14)	0.0034 (13)
C3	0.0204 (17)	0.0360 (19)	0.0332 (18)	0.0014 (14)	0.0064 (15)	0.0030 (15)
C4	0.0199 (17)	0.0312 (18)	0.0332 (18)	−0.0029 (14)	0.0003 (14)	−0.0010 (14)
C5	0.0209 (17)	0.0231 (16)	0.0262 (16)	0.0013 (13)	−0.0009 (13)	0.0034 (13)
C6	0.0203 (17)	0.0292 (17)	0.0311 (17)	0.0002 (13)	0.0035 (14)	0.0023 (14)
C7	0.0214 (17)	0.0306 (18)	0.0303 (17)	−0.0017 (14)	0.0012 (14)	−0.0005 (14)
C8	0.0196 (16)	0.0231 (16)	0.0290 (16)	0.0002 (13)	−0.0020 (13)	0.0030 (13)
C9	0.0230 (17)	0.0279 (17)	0.0261 (16)	0.0001 (14)	0.0045 (14)	0.0043 (14)
C10	0.0249 (18)	0.0283 (17)	0.0290 (17)	0.0051 (14)	−0.0019 (14)	−0.0024 (14)
C11	0.0185 (16)	0.0265 (17)	0.0291 (16)	0.0049 (13)	0.0034 (13)	0.0005 (13)
C12	0.0151 (16)	0.0272 (17)	0.0355 (18)	0.0012 (13)	0.0041 (14)	−0.0025 (14)
C13	0.0169 (16)	0.0276 (17)	0.0342 (18)	0.0044 (13)	0.0029 (14)	−0.0012 (14)
C14	0.0156 (16)	0.0309 (18)	0.0371 (18)	0.0004 (13)	0.0028 (14)	−0.0020 (15)
C15	0.0217 (17)	0.0355 (19)	0.0308 (17)	−0.0002 (14)	0.0044 (14)	−0.0010 (15)
C16	0.0193 (17)	0.0306 (18)	0.0350 (18)	0.0046 (14)	0.0001 (14)	−0.0035 (15)
C17	0.0169 (16)	0.0317 (18)	0.0373 (19)	0.0002 (14)	0.0027 (14)	−0.0037 (15)
C18	0.0210 (17)	0.0300 (17)	0.0329 (17)	0.0012 (14)	0.0043 (14)	−0.0028 (15)
C19	0.0221 (18)	0.046 (2)	0.0344 (18)	0.0029 (15)	−0.0023 (15)	−0.0011 (16)

S1—C9	1.733 (3)	C4—H4	0.9500
S1—C8	1.739 (3)	C5—C6	1.398 (4)
S2—C9	1.753 (3)	C5—C8	1.465 (4)
S2—C10	1.810 (3)	C6—C7	1.383 (4)
S3—C11	1.745 (3)	C6—H6	0.9500
S3—C10	1.801 (3)	C7—H7	0.9500
S4—C11	1.725 (3)	C10—H10A	0.9900
S4—C12	1.743 (3)	C10—H10B	0.9900
N1—C8	1.304 (4)	C12—C13	1.469 (4)
N1—N2	1.393 (4)	C13—C14	1.394 (4)
N2—C9	1.297 (4)	C13—C18	1.397 (4)
N3—C11	1.310 (4)	C14—C15	1.386 (4)
N3—N4	1.393 (4)	C14—H14	0.9500
N4—C12	1.311 (4)	C15—C16	1.391 (4)
C1—C2	1.510 (4)	C15—H15	0.9500
C1—H1A	0.9800	C16—C17	1.403 (5)
C1—H1B	0.9800	C16—C19	1.506 (4)
C1—H1C	0.9800	C17—C18	1.386 (5)
C2—C7	1.398 (4)	C17—H17	0.9500
C2—C3	1.403 (4)	C18—H18	0.9500
C3—C4	1.382 (4)	C19—H19A	0.9800
C3—H3	0.9500	C19—H19B	0.9800
C4—C5	1.393 (4)	C19—H19C	0.9800
C9—S1—C8	87.06 (15)	S1—C9—S2	119.18 (19)
C9—S2—C10	99.51 (15)	S3—C10—S2	115.46 (17)
C11—S3—C10	98.52 (15)	S3—C10—H10A	108.4
C11—S4—C12	87.24 (15)	S2—C10—H10A	108.4
C8—N1—N2	113.2 (3)	S3—C10—H10B	108.4
C9—N2—N1	111.9 (3)	S2—C10—H10B	108.4
C11—N3—N4	111.6 (3)	H10A—C10—H10B	107.5
C12—N4—N3	113.2 (3)	N3—C11—S4	114.7 (2)
C2—C1—H1A	109.5	N3—C11—S3	123.5 (2)
C2—C1—H1B	109.5	S4—C11—S3	121.77 (18)
H1A—C1—H1B	109.5	N4—C12—C13	123.9 (3)
C2—C1—H1C	109.5	N4—C12—S4	113.2 (2)
H1A—C1—H1C	109.5	C13—C12—S4	123.0 (2)
H1B—C1—H1C	109.5	C14—C13—C18	118.6 (3)
C7—C2—C3	117.7 (3)	C14—C13—C12	121.2 (3)
C7—C2—C1	121.0 (3)	C18—C13—C12	120.1 (3)
C3—C2—C1	121.3 (3)	C15—C14—C13	120.3 (3)
C4—C3—C2	121.4 (3)	C15—C14—H14	119.8
C4—C3—H3	119.3	C13—C14—H14	119.8
C2—C3—H3	119.3	C14—C15—C16	121.9 (3)
C3—C4—C5	120.2 (3)	C14—C15—H15	119.1
C3—C4—H4	119.9	C16—C15—H15	119.1
C5—C4—H4	119.9	C15—C16—C17	117.3 (3)
C4—C5—C6	119.2 (3)	C15—C16—C19	122.4 (3)
C4—C5—C8	121.0 (3)	C17—C16—C19	120.3 (3)
C6—C5—C8	119.8 (3)	C18—C17—C16	121.4 (3)
C7—C6—C5	120.2 (3)	C18—C17—H17	119.3
C7—C6—H6	119.9	C16—C17—H17	119.3
C5—C6—H6	119.9	C17—C18—C13	120.4 (3)
C6—C7—C2	121.3 (3)	C17—C18—H18	119.8
C6—C7—H7	119.3	C13—C18—H18	119.8
C2—C7—H7	119.3	C16—C19—H19A	109.5
N1—C8—C5	124.5 (3)	C16—C19—H19B	109.5
N1—C8—S1	113.2 (2)	H19A—C19—H19B	109.5
C5—C8—S1	122.3 (2)	C16—C19—H19C	109.5
N2—C9—S1	114.6 (2)	H19A—C19—H19C	109.5
N2—C9—S2	126.2 (3)	H19B—C19—H19C	109.5
C8—N1—N2—C9	1.0 (4)	C11—S3—C10—S2	67.8 (2)
C11—N3—N4—C12	0.4 (4)	C9—S2—C10—S3	104.05 (19)
C7—C2—C3—C4	−1.3 (5)	N4—N3—C11—S4	−0.1 (3)
C1—C2—C3—C4	178.2 (3)	N4—N3—C11—S3	178.8 (2)
C2—C3—C4—C5	0.4 (5)	C12—S4—C11—N3	−0.2 (3)
C3—C4—C5—C6	0.1 (5)	C12—S4—C11—S3	−179.1 (2)
C3—C4—C5—C8	−179.6 (3)	C10—S3—C11—N3	−2.0 (3)
C4—C5—C6—C7	0.2 (5)	C10—S3—C11—S4	176.80 (19)
C8—C5—C6—C7	179.9 (3)	N3—N4—C12—C13	−179.3 (3)
C5—C6—C7—C2	−1.0 (5)	N3—N4—C12—S4	−0.6 (3)
C3—C2—C7—C6	1.6 (5)	C11—S4—C12—N4	0.4 (2)
C1—C2—C7—C6	−177.9 (3)	C11—S4—C12—C13	179.2 (3)
N2—N1—C8—C5	178.9 (3)	N4—C12—C13—C14	−179.8 (3)
N2—N1—C8—S1	−0.9 (3)	S4—C12—C13—C14	1.6 (4)
C4—C5—C8—N1	179.1 (3)	N4—C12—C13—C18	0.3 (5)
C6—C5—C8—N1	−0.7 (5)	S4—C12—C13—C18	−178.3 (2)
C4—C5—C8—S1	−1.2 (4)	C18—C13—C14—C15	−0.8 (5)
C6—C5—C8—S1	179.1 (2)	C12—C13—C14—C15	179.3 (3)
C9—S1—C8—N1	0.4 (2)	C13—C14—C15—C16	−0.5 (5)
C9—S1—C8—C5	−179.4 (3)	C14—C15—C16—C17	1.5 (5)
N1—N2—C9—S1	−0.7 (3)	C14—C15—C16—C19	−177.1 (3)
N1—N2—C9—S2	−178.4 (2)	C15—C16—C17—C18	−1.3 (5)
C8—S1—C9—N2	0.2 (3)	C19—C16—C17—C18	177.4 (3)
C8—S1—C9—S2	178.1 (2)	C16—C17—C18—C13	0.0 (5)
C10—S2—C9—N2	−16.9 (3)	C14—C13—C18—C17	1.0 (5)
C10—S2—C9—S1	165.53 (19)	C12—C13—C18—C17	−179.1 (3)