3,6-Bis(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

In the mol-ecule of the title compound, C(21)H(22)N(4)O(6)S, the planar central heterocyclic ring system is oriented with respect to the trimethoxy-phenyl rings at dihedral angles of 2.60 (5) and 3.60 (6)°. Intra-molecular C-H⋯N and C-H⋯S hydrogen bonds result in the formation of planar five- and six-membered rings. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules. There is a C-H⋯π contact between a methyl group and a trimethoxy-phenyl ring, and a π-π contact between the central heterocyclic ring system and a trimethoxy-phenyl ring [centroid-centroid distance = 3.640 (1) Å].

Related literature

For general background, see: Karabasanagouda et al. (2007 ▶); Mathew et al. (2007 ▶).

Experimental

Crystal data

C21H22N4O6S

M = 458.49

Triclinic,

a = 8.6762 (17) Å

b = 8.9289 (18) Å

c = 13.735 (3) Å

α = 94.50 (3)°

β = 90.82 (3)°

γ = 90.47 (3)°

V = 1060.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 113 (2) K

0.22 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.957, T max = 0.980

6899 measured reflections

3720 independent reflections

3102 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.137

S = 1.19

3720 reflections

295 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.56 e Å−3

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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022502/hk2498sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022502/hk2498Isup2.hkl

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

C21H22N4O6S	Z = 2
Mr = 458.49	F000 = 480
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Melting point: 423 K
a = 8.6762 (17) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.9289 (18) Å	Cell parameters from 3022 reflections
c = 13.735 (3) Å	θ = 2.8–27.9º
α = 94.50 (3)º	µ = 0.20 mm−1
β = 90.82 (3)º	T = 113 (2) K
γ = 90.47 (3)º	Prism, colorless
V = 1060.6 (4) Å3	0.22 × 0.20 × 0.10 mm

Rigaku Saturn CCD area-detector diffractometer	3720 independent reflections
Radiation source: rotating anode	3102 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.022
T = 113(2) K	θmax = 25.0º
ω scans	θmin = 2.8º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	h = −7→10
Tmin = 0.957, Tmax = 0.980	k = −10→10
6899 measured reflections	l = −15→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0797P)2 + 0.2575P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max = 0.003
3720 reflections	Δρmax = 0.93 e Å−3
295 parameters	Δρmin = −0.55 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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	0.50010 (6)	0.76590 (6)	0.89162 (4)	0.01987 (19)
O1	−0.04182 (18)	0.27249 (17)	1.14986 (12)	0.0270 (4)
O2	−0.17317 (18)	0.40003 (18)	1.31069 (12)	0.0282 (4)
O3	−0.09095 (19)	0.67584 (18)	1.38496 (11)	0.0290 (4)
O4	0.6387 (2)	0.3996 (2)	0.57836 (12)	0.0352 (4)
O5	0.5139 (3)	0.1310 (2)	0.59409 (12)	0.0457 (5)
O6	0.3352 (2)	0.07371 (18)	0.74567 (12)	0.0305 (4)
N1	0.2808 (2)	0.88200 (19)	1.13007 (13)	0.0207 (4)
N2	0.3818 (2)	0.9307 (2)	1.06090 (13)	0.0220 (4)
N3	0.31915 (19)	0.69318 (18)	1.02331 (12)	0.0161 (4)
N4	0.3240 (2)	0.56265 (19)	0.96337 (12)	0.0173 (4)
C1	0.1406 (2)	0.6468 (2)	1.16140 (15)	0.0175 (4)
C2	0.1044 (2)	0.5002 (2)	1.12685 (15)	0.0197 (5)
H2	0.1477	0.4583	1.0695	0.024*
C3	0.0031 (2)	0.4170 (2)	1.17875 (16)	0.0204 (5)
C4	−0.0631 (2)	0.4788 (2)	1.26440 (16)	0.0209 (5)
C5	−0.0226 (2)	0.6260 (2)	1.29933 (15)	0.0205 (5)
C6	0.0775 (2)	0.7102 (2)	1.24824 (14)	0.0193 (5)
H6	0.1029	0.8082	1.2713	0.023*
C7	0.0400 (3)	0.1984 (3)	1.07097 (18)	0.0311 (6)
H7A	0.0241	0.2505	1.0131	0.047*
H7B	0.0029	0.0969	1.0596	0.047*
H7C	0.1480	0.1981	1.0871	0.047*
C8	−0.1128 (3)	0.3006 (3)	1.37736 (19)	0.0356 (6)
H8A	−0.0456	0.2300	1.3435	0.053*
H8B	−0.1961	0.2475	1.4051	0.053*
H8C	−0.0561	0.3572	1.4285	0.053*
C9	−0.0618 (3)	0.8283 (3)	1.41985 (17)	0.0354 (6)
H9A	0.0469	0.8435	1.4308	0.053*
H9B	−0.1152	0.8504	1.4800	0.053*
H9C	−0.0976	0.8936	1.3722	0.053*
C10	0.2438 (2)	0.7397 (2)	1.10791 (15)	0.0184 (5)
C11	0.4024 (2)	0.8140 (2)	0.99828 (15)	0.0178 (4)
C12	0.4137 (2)	0.5860 (2)	0.89114 (15)	0.0175 (4)
C13	0.4421 (2)	0.4679 (2)	0.81339 (15)	0.0179 (5)
C14	0.5310 (2)	0.4968 (3)	0.73302 (15)	0.0218 (5)
H14	0.5742	0.5916	0.7283	0.026*
C15	0.5545 (3)	0.3832 (3)	0.66039 (16)	0.0260 (5)
C16	0.4910 (3)	0.2408 (3)	0.66800 (16)	0.0285 (5)
C17	0.3990 (3)	0.2149 (2)	0.74754 (16)	0.0233 (5)
C18	0.3746 (2)	0.3271 (2)	0.82064 (15)	0.0201 (5)
H18	0.3140	0.3090	0.8739	0.024*
C19	0.6870 (3)	0.5477 (3)	0.56178 (19)	0.0390 (6)
H19A	0.5995	0.6131	0.5647	0.058*
H19B	0.7325	0.5476	0.4985	0.058*
H19C	0.7615	0.5827	0.6109	0.058*
C20	0.5942 (4)	−0.0017 (3)	0.6225 (2)	0.0512 (8)
H20A	0.6491	0.0223	0.6830	0.077*
H20B	0.6657	−0.0343	0.5727	0.077*
H20C	0.5207	−0.0806	0.6307	0.077*
C21	0.2401 (3)	0.0431 (3)	0.82573 (17)	0.0280 (5)
H21A	0.2991	0.0570	0.8855	0.042*
H21B	0.2029	−0.0587	0.8171	0.042*
H21C	0.1543	0.1105	0.8286	0.042*

	U11	U22	U33	U12	U13	U23
S1	0.0218 (3)	0.0164 (3)	0.0217 (3)	−0.0034 (2)	0.0056 (2)	0.0029 (2)
O1	0.0264 (9)	0.0190 (8)	0.0353 (9)	−0.0065 (7)	0.0089 (7)	−0.0005 (7)
O2	0.0202 (8)	0.0324 (9)	0.0340 (9)	−0.0024 (7)	0.0086 (7)	0.0152 (7)
O3	0.0334 (9)	0.0306 (9)	0.0232 (8)	0.0000 (7)	0.0118 (7)	0.0019 (7)
O4	0.0383 (10)	0.0439 (11)	0.0231 (8)	−0.0078 (8)	0.0124 (7)	−0.0015 (7)
O5	0.0724 (14)	0.0362 (10)	0.0262 (9)	−0.0092 (10)	0.0121 (9)	−0.0138 (8)
O6	0.0376 (10)	0.0214 (8)	0.0315 (9)	−0.0086 (7)	0.0036 (7)	−0.0039 (7)
N1	0.0232 (10)	0.0171 (9)	0.0219 (9)	−0.0036 (7)	0.0039 (8)	0.0027 (7)
N2	0.0260 (10)	0.0176 (9)	0.0226 (9)	−0.0041 (8)	0.0069 (8)	0.0029 (7)
N3	0.0166 (9)	0.0137 (8)	0.0181 (9)	−0.0016 (7)	0.0019 (7)	0.0022 (7)
N4	0.0177 (9)	0.0148 (9)	0.0194 (9)	−0.0006 (7)	0.0010 (7)	0.0013 (7)
C1	0.0142 (10)	0.0191 (10)	0.0197 (10)	0.0005 (8)	0.0003 (8)	0.0049 (8)
C2	0.0172 (11)	0.0219 (11)	0.0203 (11)	−0.0007 (9)	0.0046 (9)	0.0018 (9)
C3	0.0175 (11)	0.0172 (10)	0.0270 (11)	−0.0017 (8)	0.0006 (9)	0.0044 (9)
C4	0.0152 (10)	0.0232 (11)	0.0256 (11)	−0.0002 (8)	0.0031 (9)	0.0086 (9)
C5	0.0187 (11)	0.0252 (12)	0.0181 (10)	0.0043 (9)	0.0023 (9)	0.0049 (9)
C6	0.0206 (11)	0.0181 (10)	0.0193 (11)	0.0014 (9)	−0.0008 (9)	0.0025 (8)
C7	0.0317 (13)	0.0234 (12)	0.0373 (14)	−0.0052 (10)	0.0068 (11)	−0.0041 (10)
C8	0.0365 (14)	0.0379 (14)	0.0351 (14)	−0.0037 (11)	0.0067 (11)	0.0187 (11)
C9	0.0519 (17)	0.0324 (14)	0.0218 (12)	0.0057 (12)	0.0101 (11)	−0.0018 (10)
C10	0.0184 (11)	0.0192 (10)	0.0177 (10)	0.0007 (8)	0.0004 (8)	0.0018 (8)
C11	0.0174 (10)	0.0161 (10)	0.0205 (10)	−0.0034 (8)	0.0005 (8)	0.0060 (8)
C12	0.0159 (10)	0.0175 (10)	0.0195 (10)	0.0008 (8)	−0.0010 (8)	0.0049 (8)
C13	0.0155 (10)	0.0203 (11)	0.0181 (10)	0.0007 (8)	−0.0017 (8)	0.0028 (8)
C14	0.0189 (11)	0.0260 (11)	0.0207 (11)	−0.0031 (9)	0.0001 (9)	0.0034 (9)
C15	0.0228 (12)	0.0371 (13)	0.0179 (11)	−0.0019 (10)	0.0032 (9)	0.0006 (9)
C16	0.0325 (13)	0.0310 (13)	0.0204 (11)	−0.0034 (10)	0.0021 (10)	−0.0072 (10)
C17	0.0249 (12)	0.0190 (11)	0.0253 (12)	−0.0028 (9)	−0.0031 (9)	−0.0020 (9)
C18	0.0181 (11)	0.0227 (11)	0.0198 (10)	0.0006 (9)	0.0003 (9)	0.0025 (9)
C19	0.0391 (10)	0.0433 (10)	0.0349 (9)	−0.0054 (8)	0.0068 (8)	0.0050 (8)
C20	0.0504 (11)	0.0500 (11)	0.0512 (11)	0.0040 (9)	0.0021 (9)	−0.0090 (9)
C21	0.0274 (13)	0.0211 (11)	0.0357 (13)	−0.0031 (10)	−0.0010 (10)	0.0035 (10)

S1—C11	1.729 (2)	C6—H6	0.9300
S1—C12	1.766 (2)	C7—H7A	0.9600
O1—C3	1.372 (3)	C7—H7B	0.9600
O1—C7	1.426 (3)	C7—H7C	0.9600
O2—C4	1.374 (3)	C8—H8A	0.9600
O2—C8	1.422 (3)	C8—H8B	0.9600
O3—C5	1.369 (3)	C8—H8C	0.9600
O3—C9	1.427 (3)	C9—H9A	0.9600
O4—C15	1.369 (3)	C9—H9B	0.9600
O4—C19	1.420 (3)	C9—H9C	0.9600
O5—C16	1.372 (3)	C12—C13	1.465 (3)
O5—C20	1.456 (4)	C13—C18	1.394 (3)
O6—C17	1.371 (3)	C13—C14	1.395 (3)
O6—C21	1.426 (3)	C14—C15	1.384 (3)
N1—C10	1.319 (3)	C14—H14	0.9300
N1—N2	1.394 (3)	C15—C16	1.394 (3)
N2—C11	1.313 (3)	C16—C17	1.395 (3)
N3—C11	1.363 (3)	C17—C18	1.382 (3)
N3—N4	1.374 (2)	C18—H18	0.9300
N3—C10	1.379 (3)	C19—H19A	0.9600
N4—C12	1.299 (3)	C19—H19B	0.9600
C1—C2	1.389 (3)	C19—H19C	0.9600
C1—C6	1.400 (3)	C20—H20A	0.9600
C1—C10	1.460 (3)	C20—H20B	0.9600
C2—C3	1.387 (3)	C20—H20C	0.9600
C2—H2	0.9300	C21—H21A	0.9600
C3—C4	1.393 (3)	C21—H21B	0.9600
C4—C5	1.403 (3)	C21—H21C	0.9600
C5—C6	1.380 (3)
C11—S1—C12	87.61 (10)	H9A—C9—H9C	109.5
C3—O1—C7	116.73 (17)	H9B—C9—H9C	109.5
C4—O2—C8	114.35 (17)	N1—C10—N3	107.57 (18)
C5—O3—C9	116.88 (18)	N1—C10—C1	127.0 (2)
C15—O4—C19	116.8 (2)	N3—C10—C1	125.41 (19)
C16—O5—C20	115.3 (2)	N2—C11—N3	110.97 (18)
C17—O6—C21	116.75 (17)	N2—C11—S1	139.70 (16)
C10—N1—N2	109.70 (17)	N3—C11—S1	109.32 (15)
C11—N2—N1	105.61 (16)	N4—C12—C13	121.29 (19)
C11—N3—N4	118.40 (17)	N4—C12—S1	116.85 (16)
C11—N3—C10	106.15 (17)	C13—C12—S1	121.85 (16)
N4—N3—C10	135.43 (17)	C18—C13—C14	120.9 (2)
C12—N4—N3	107.81 (17)	C18—C13—C12	118.23 (19)
C2—C1—C6	120.74 (19)	C14—C13—C12	120.9 (2)
C2—C1—C10	121.14 (19)	C15—C14—C13	119.4 (2)
C6—C1—C10	118.12 (19)	C15—C14—H14	120.3
C3—C2—C1	119.3 (2)	C13—C14—H14	120.3
C3—C2—H2	120.4	O4—C15—C14	124.2 (2)
C1—C2—H2	120.4	O4—C15—C16	115.5 (2)
O1—C3—C2	123.7 (2)	C14—C15—C16	120.3 (2)
O1—C3—C4	115.37 (19)	O5—C16—C15	119.0 (2)
C2—C3—C4	120.9 (2)	O5—C16—C17	121.3 (2)
O2—C4—C3	120.4 (2)	C15—C16—C17	119.6 (2)
O2—C4—C5	120.5 (2)	O6—C17—C18	124.0 (2)
C3—C4—C5	118.98 (19)	O6—C17—C16	115.1 (2)
O3—C5—C6	124.52 (19)	C18—C17—C16	120.8 (2)
O3—C5—C4	114.81 (19)	C17—C18—C13	119.0 (2)
C6—C5—C4	120.67 (19)	C17—C18—H18	120.5
C5—C6—C1	119.37 (19)	C13—C18—H18	120.5
C5—C6—H6	120.3	O4—C19—H19A	109.5
C1—C6—H6	120.3	O4—C19—H19B	109.5
O1—C7—H7A	109.5	H19A—C19—H19B	109.5
O1—C7—H7B	109.5	O4—C19—H19C	109.5
H7A—C7—H7B	109.5	H19A—C19—H19C	109.5
O1—C7—H7C	109.5	H19B—C19—H19C	109.5
H7A—C7—H7C	109.5	O5—C20—H20A	109.5
H7B—C7—H7C	109.5	O5—C20—H20B	109.5
O2—C8—H8A	109.5	H20A—C20—H20B	109.5
O2—C8—H8B	109.5	O5—C20—H20C	109.5
H8A—C8—H8B	109.5	H20A—C20—H20C	109.5
O2—C8—H8C	109.5	H20B—C20—H20C	109.5
H8A—C8—H8C	109.5	O6—C21—H21A	109.5
H8B—C8—H8C	109.5	O6—C21—H21B	109.5
O3—C9—H9A	109.5	H21A—C21—H21B	109.5
O3—C9—H9B	109.5	O6—C21—H21C	109.5
H9A—C9—H9B	109.5	H21A—C21—H21C	109.5
O3—C9—H9C	109.5	H21B—C21—H21C	109.5
C10—N1—N2—C11	0.1 (2)	N4—N3—C11—N2	177.96 (17)
C11—N3—N4—C12	0.1 (2)	C10—N3—C11—N2	−0.6 (2)
C10—N3—N4—C12	178.2 (2)	N4—N3—C11—S1	−0.9 (2)
C6—C1—C2—C3	0.8 (3)	C10—N3—C11—S1	−179.49 (13)
C10—C1—C2—C3	−178.50 (19)	C12—S1—C11—N2	−177.3 (3)
C7—O1—C3—C2	10.3 (3)	C12—S1—C11—N3	1.03 (15)
C7—O1—C3—C4	−171.13 (19)	N3—N4—C12—C13	−179.48 (17)
C1—C2—C3—O1	178.88 (19)	N3—N4—C12—S1	0.8 (2)
C1—C2—C3—C4	0.4 (3)	C11—S1—C12—N4	−1.12 (17)
C8—O2—C4—C3	86.6 (3)	C11—S1—C12—C13	179.16 (18)
C8—O2—C4—C5	−97.3 (2)	N4—C12—C13—C18	−2.4 (3)
O1—C3—C4—O2	−4.2 (3)	S1—C12—C13—C18	177.34 (15)
C2—C3—C4—O2	174.44 (19)	N4—C12—C13—C14	176.02 (19)
O1—C3—C4—C5	179.64 (19)	S1—C12—C13—C14	−4.3 (3)
C2—C3—C4—C5	−1.7 (3)	C18—C13—C14—C15	−1.1 (3)
C9—O3—C5—C6	3.6 (3)	C12—C13—C14—C15	−179.42 (19)
C9—O3—C5—C4	−175.7 (2)	C19—O4—C15—C14	−8.6 (3)
O2—C4—C5—O3	5.2 (3)	C19—O4—C15—C16	171.6 (2)
C3—C4—C5—O3	−178.67 (18)	C13—C14—C15—O4	179.6 (2)
O2—C4—C5—C6	−174.19 (18)	C13—C14—C15—C16	−0.6 (3)
C3—C4—C5—C6	2.0 (3)	C20—O5—C16—C15	119.7 (3)
O3—C5—C6—C1	179.86 (19)	C20—O5—C16—C17	−63.8 (3)
C4—C5—C6—C1	−0.9 (3)	O4—C15—C16—O5	−1.3 (3)
C2—C1—C6—C5	−0.5 (3)	C14—C15—C16—O5	178.9 (2)
C10—C1—C6—C5	178.77 (18)	O4—C15—C16—C17	−177.9 (2)
N2—N1—C10—N3	−0.4 (2)	C14—C15—C16—C17	2.3 (4)
N2—N1—C10—C1	−179.76 (19)	C21—O6—C17—C18	−1.0 (3)
C11—N3—C10—N1	0.6 (2)	C21—O6—C17—C16	−179.9 (2)
N4—N3—C10—N1	−177.6 (2)	O5—C16—C17—O6	0.1 (3)
C11—N3—C10—C1	179.98 (19)	C15—C16—C17—O6	176.6 (2)
N4—N3—C10—C1	1.7 (4)	O5—C16—C17—C18	−178.8 (2)
C2—C1—C10—N1	176.3 (2)	C15—C16—C17—C18	−2.3 (4)
C6—C1—C10—N1	−3.1 (3)	O6—C17—C18—C13	−178.1 (2)
C2—C1—C10—N3	−2.9 (3)	C16—C17—C18—C13	0.7 (3)
C6—C1—C10—N3	177.75 (18)	C14—C13—C18—C17	1.1 (3)
N1—N2—C11—N3	0.4 (2)	C12—C13—C18—C17	179.43 (19)
N1—N2—C11—S1	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.93	2.36	3.047 (3)	130
C14—H14···S1	0.93	2.72	3.130 (3)	108
C19—H19B···O3i	0.96	2.53	3.384 (2)	148
C21—H21B···O1ii	0.96	2.43	3.331 (3)	156
C19—H19C···Cg3iii	0.96	3.30	4.057 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4	0.93	2.36	3.047 (3)	130
C14—H14⋯S1	0.93	2.72	3.130 (3)	108
C19—H19B⋯O3i	0.96	2.53	3.384 (2)	148
C21—H21B⋯O1ii	0.96	2.43	3.331 (3)	156
C19—H19C⋯Cg3iii	0.96	3.30	4.057 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) . Cg3 is the centroid of the trimethoxyphenyl ring C1–C6.