3-Phenyl-4-{3-[(p-tol-yloxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}sydnone.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 3-phenyl-4-{3-[(p-tol-yloxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-1,2,3-oxadiazol-3-ium-5-olate), C(20)H(16)N(6)O(3)S, an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The 1,2,3-oxadiazole and 1,2,4-triazole rings are inclined to each other at an inter-planar angle of 44.13 (13)°. The phenyl ring makes an inter-planar angle of 67.40 (13)° with the attached 1,2,3-oxadiazole ring. In the crystal structure, adjacent mol-ecules are inter-connected into two-mol-ecule-thick arrays parallel to (100) via C-H⋯O and C-H⋯N hydrogen bonds. A short S⋯O contact [2.9512 (18) Å] is observed.

Related literature

For general background to, and applications of materials related to the title compound, see: Hedge et al. (2008 ▶), Kalluraya & Rahiman (1997 ▶); Kalluraya et al. (2003 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Goh et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H16N6O3S

M = 420.45

Monoclinic,

a = 42.0781 (12) Å

b = 8.2304 (2) Å

c = 11.1488 (3) Å

β = 101.630 (2)°

V = 3781.78 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.29 × 0.13 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.989

11383 measured reflections

3486 independent reflections

2496 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.101

S = 1.03

3486 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.40 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 datablocks global, I. DOI: 10.1107/S160053681002982X/hb5565sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002982X/hb5565Isup2.hkl

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

C20H16N6O3S	F(000) = 1744
Mr = 420.45	Dx = 1.477 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2771 reflections
a = 42.0781 (12) Å	θ = 2.5–30.0°
b = 8.2304 (2) Å	µ = 0.21 mm−1
c = 11.1488 (3) Å	T = 100 K
β = 101.630 (2)°	Block, colourless
V = 3781.78 (17) Å3	0.29 × 0.13 × 0.05 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	2496 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −50→48
Tmin = 0.942, Tmax = 0.989	k = −9→9
11383 measured reflections	l = −13→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0388P)2 + 2.5537P] where P = (Fo2 + 2Fc2)/3
3486 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.220066 (15)	0.57970 (8)	0.11452 (6)	0.01457 (18)
O1	0.10960 (4)	0.4996 (2)	0.35734 (14)	0.0177 (4)
O2	0.19581 (4)	−0.0842 (2)	−0.00307 (14)	0.0172 (4)
O3	0.24309 (4)	0.0525 (2)	0.06238 (15)	0.0184 (4)
N1	0.16869 (5)	0.7388 (3)	0.34427 (18)	0.0153 (5)
N2	0.19003 (5)	0.7681 (3)	0.26397 (18)	0.0152 (5)
N3	0.17980 (5)	0.5056 (3)	0.26683 (17)	0.0129 (5)
N4	0.17428 (5)	0.3462 (3)	0.22624 (17)	0.0129 (5)
N5	0.16398 (5)	−0.0737 (3)	0.00868 (18)	0.0167 (5)
N6	0.16286 (5)	0.0537 (3)	0.07725 (18)	0.0132 (5)
C1	0.05562 (6)	0.4348 (4)	0.3630 (2)	0.0206 (7)
H1A	0.0495	0.4827	0.2862	0.025*
C2	0.03244 (6)	0.3680 (4)	0.4195 (2)	0.0245 (7)
H2A	0.0108	0.3711	0.3796	0.029*
C3	0.04051 (6)	0.2958 (4)	0.5348 (2)	0.0204 (7)
C4	0.07298 (6)	0.2943 (3)	0.5906 (2)	0.0211 (7)
H4A	0.0790	0.2479	0.6679	0.025*
C5	0.09682 (6)	0.3592 (3)	0.5357 (2)	0.0187 (6)
H5A	0.1185	0.3552	0.5753	0.022*
C6	0.08808 (6)	0.4304 (3)	0.4209 (2)	0.0159 (6)
C7	0.14297 (6)	0.4960 (4)	0.4192 (2)	0.0163 (6)
H7A	0.1503	0.3844	0.4318	0.020*
H7B	0.1454	0.5481	0.4986	0.020*
C8	0.16269 (6)	0.5830 (3)	0.3431 (2)	0.0135 (6)
C9	0.19615 (6)	0.6265 (3)	0.2203 (2)	0.0129 (6)
C10	0.22834 (6)	0.3743 (3)	0.1735 (2)	0.0139 (6)
H10A	0.2405	0.3153	0.1223	0.017*
H10B	0.2414	0.3788	0.2558	0.017*
C11	0.19694 (6)	0.2875 (3)	0.1751 (2)	0.0111 (6)
C12	0.19158 (6)	0.1326 (3)	0.1140 (2)	0.0117 (6)
C13	0.21431 (6)	0.0430 (3)	0.0616 (2)	0.0138 (6)
C14	0.13078 (6)	0.0942 (3)	0.0973 (2)	0.0145 (6)
C15	0.10783 (6)	0.1424 (3)	−0.0032 (2)	0.0178 (6)
H15A	0.1131	0.1511	−0.0802	0.021*
C16	0.07679 (6)	0.1774 (4)	0.0136 (2)	0.0230 (7)
H16A	0.0608	0.2094	−0.0526	0.028*
C17	0.06952 (6)	0.1648 (3)	0.1288 (2)	0.0225 (7)
H17A	0.0487	0.1896	0.1399	0.027*
C18	0.09303 (6)	0.1153 (3)	0.2280 (2)	0.0210 (7)
H18A	0.0879	0.1066	0.3050	0.025*
C19	0.12400 (6)	0.0791 (3)	0.2130 (2)	0.0173 (6)
H19A	0.1399	0.0453	0.2789	0.021*
C20	0.01502 (7)	0.2227 (4)	0.5972 (3)	0.0314 (8)
H20D	0.0252	0.1820	0.6764	0.047*
H20A	0.0043	0.1352	0.5483	0.047*
H20B	−0.0006	0.3044	0.6066	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0188 (3)	0.0096 (4)	0.0166 (3)	0.0008 (3)	0.0066 (2)	−0.0007 (3)
O1	0.0168 (9)	0.0222 (12)	0.0141 (9)	−0.0022 (9)	0.0028 (7)	0.0017 (9)
O2	0.0226 (10)	0.0125 (11)	0.0172 (9)	0.0016 (9)	0.0059 (7)	−0.0051 (9)
O3	0.0185 (10)	0.0192 (12)	0.0184 (9)	0.0015 (9)	0.0057 (7)	−0.0013 (9)
N1	0.0197 (12)	0.0147 (14)	0.0119 (11)	0.0013 (11)	0.0039 (9)	−0.0007 (11)
N2	0.0194 (12)	0.0124 (14)	0.0144 (11)	0.0007 (10)	0.0050 (9)	−0.0002 (11)
N3	0.0160 (11)	0.0083 (13)	0.0140 (11)	0.0006 (10)	0.0026 (9)	−0.0036 (11)
N4	0.0200 (11)	0.0073 (13)	0.0116 (10)	0.0006 (10)	0.0033 (9)	0.0009 (11)
N5	0.0208 (12)	0.0139 (14)	0.0156 (11)	0.0019 (11)	0.0044 (9)	−0.0011 (12)
N6	0.0202 (12)	0.0088 (13)	0.0101 (10)	0.0031 (10)	0.0021 (8)	0.0001 (11)
C1	0.0234 (14)	0.0203 (18)	0.0171 (14)	−0.0002 (14)	0.0020 (11)	−0.0008 (14)
C2	0.0171 (14)	0.0258 (19)	0.0298 (16)	−0.0009 (14)	0.0030 (11)	−0.0038 (15)
C3	0.0232 (15)	0.0153 (17)	0.0245 (15)	−0.0003 (13)	0.0093 (12)	−0.0029 (14)
C4	0.0292 (16)	0.0193 (18)	0.0164 (14)	0.0005 (14)	0.0086 (12)	0.0016 (14)
C5	0.0179 (14)	0.0181 (17)	0.0202 (14)	0.0017 (13)	0.0036 (11)	0.0007 (14)
C6	0.0206 (14)	0.0108 (16)	0.0179 (13)	0.0008 (13)	0.0074 (10)	−0.0028 (13)
C7	0.0163 (13)	0.0182 (17)	0.0141 (13)	0.0026 (13)	0.0024 (10)	0.0003 (13)
C8	0.0142 (13)	0.0140 (16)	0.0119 (12)	0.0023 (13)	0.0015 (10)	−0.0012 (14)
C9	0.0162 (13)	0.0105 (16)	0.0112 (13)	−0.0009 (12)	0.0004 (10)	0.0014 (13)
C10	0.0171 (13)	0.0079 (16)	0.0168 (13)	0.0030 (12)	0.0035 (10)	0.0011 (13)
C11	0.0171 (13)	0.0072 (15)	0.0078 (12)	0.0042 (12)	−0.0003 (10)	0.0019 (12)
C12	0.0139 (13)	0.0099 (15)	0.0110 (12)	0.0008 (12)	0.0018 (10)	0.0013 (12)
C13	0.0263 (15)	0.0057 (16)	0.0086 (12)	−0.0009 (13)	0.0016 (10)	0.0015 (12)
C14	0.0152 (13)	0.0099 (16)	0.0181 (13)	−0.0043 (12)	0.0025 (10)	−0.0021 (13)
C15	0.0222 (14)	0.0157 (17)	0.0149 (13)	−0.0029 (13)	0.0026 (11)	0.0012 (13)
C16	0.0210 (15)	0.0209 (19)	0.0256 (15)	−0.0005 (14)	0.0009 (11)	0.0035 (15)
C17	0.0207 (14)	0.0170 (18)	0.0316 (16)	0.0002 (13)	0.0094 (12)	−0.0016 (15)
C18	0.0284 (15)	0.0171 (18)	0.0198 (14)	−0.0048 (14)	0.0105 (12)	−0.0033 (13)
C19	0.0253 (14)	0.0123 (16)	0.0131 (13)	−0.0032 (13)	0.0010 (10)	0.0009 (13)
C20	0.0276 (16)	0.031 (2)	0.0377 (18)	−0.0037 (15)	0.0126 (13)	−0.0001 (17)

S1—C9	1.741 (2)	C4—H4A	0.9300
S1—C10	1.822 (3)	C5—C6	1.387 (3)
O1—C6	1.381 (3)	C5—H5A	0.9300
O1—C7	1.435 (3)	C7—C8	1.485 (3)
O2—N5	1.375 (2)	C7—H7A	0.9700
O2—C13	1.413 (3)	C7—H7B	0.9700
O3—C13	1.212 (3)	C10—C11	1.505 (3)
N1—C8	1.306 (3)	C10—H10A	0.9700
N1—N2	1.411 (3)	C10—H10B	0.9700
N2—C9	1.309 (3)	C11—C12	1.442 (4)
N3—C9	1.369 (3)	C12—C13	1.423 (3)
N3—C8	1.376 (3)	C14—C19	1.382 (3)
N3—N4	1.392 (3)	C14—C15	1.382 (3)
N4—C11	1.299 (3)	C15—C16	1.387 (3)
N5—N6	1.304 (3)	C15—H15A	0.9300
N6—C12	1.360 (3)	C16—C17	1.382 (4)
N6—C14	1.451 (3)	C16—H16A	0.9300
C1—C2	1.378 (4)	C17—C18	1.388 (4)
C1—C6	1.389 (3)	C17—H17A	0.9300
C1—H1A	0.9300	C18—C19	1.380 (3)
C2—C3	1.395 (4)	C18—H18A	0.9300
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.382 (3)	C20—H20D	0.9600
C3—C20	1.516 (4)	C20—H20A	0.9600
C4—C5	1.384 (3)	C20—H20B	0.9600
C9—S1—C10	93.16 (12)	N2—C9—S1	129.3 (2)
C6—O1—C7	115.08 (18)	N3—C9—S1	119.9 (2)
N5—O2—C13	110.62 (18)	C11—C10—S1	109.88 (17)
C8—N1—N2	107.9 (2)	C11—C10—H10A	109.7
C9—N2—N1	106.4 (2)	S1—C10—H10A	109.7
C9—N3—C8	105.3 (2)	C11—C10—H10B	109.7
C9—N3—N4	128.70 (19)	S1—C10—H10B	109.7
C8—N3—N4	124.3 (2)	H10A—C10—H10B	108.2
C11—N4—N3	113.8 (2)	N4—C11—C12	118.5 (2)
N6—N5—O2	104.90 (18)	N4—C11—C10	123.5 (2)
N5—N6—C12	115.2 (2)	C12—C11—C10	117.9 (2)
N5—N6—C14	114.8 (2)	N6—C12—C13	105.0 (2)
C12—N6—C14	129.9 (2)	N6—C12—C11	127.6 (2)
C2—C1—C6	119.8 (2)	C13—C12—C11	126.7 (2)
C2—C1—H1A	120.1	O3—C13—O2	119.9 (2)
C6—C1—H1A	120.1	O3—C13—C12	135.8 (2)
C1—C2—C3	121.9 (2)	O2—C13—C12	104.3 (2)
C1—C2—H2A	119.1	C19—C14—C15	122.7 (2)
C3—C2—H2A	119.1	C19—C14—N6	119.8 (2)
C4—C3—C2	117.0 (2)	C15—C14—N6	117.5 (2)
C4—C3—C20	121.1 (2)	C14—C15—C16	118.2 (2)
C2—C3—C20	121.9 (2)	C14—C15—H15A	120.9
C3—C4—C5	122.4 (3)	C16—C15—H15A	120.9
C3—C4—H4A	118.8	C17—C16—C15	120.1 (2)
C5—C4—H4A	118.8	C17—C16—H16A	120.0
C4—C5—C6	119.3 (2)	C15—C16—H16A	120.0
C4—C5—H5A	120.3	C16—C17—C18	120.4 (2)
C6—C5—H5A	120.3	C16—C17—H17A	119.8
O1—C6—C5	124.7 (2)	C18—C17—H17A	119.8
O1—C6—C1	115.8 (2)	C19—C18—C17	120.4 (2)
C5—C6—C1	119.5 (2)	C19—C18—H18A	119.8
O1—C7—C8	108.69 (19)	C17—C18—H18A	119.8
O1—C7—H7A	110.0	C18—C19—C14	118.1 (2)
C8—C7—H7A	110.0	C18—C19—H19A	120.9
O1—C7—H7B	110.0	C14—C19—H19A	120.9
C8—C7—H7B	110.0	C3—C20—H20D	109.5
H7A—C7—H7B	108.3	C3—C20—H20A	109.5
N1—C8—N3	109.7 (2)	H20D—C20—H20A	109.5
N1—C8—C7	126.6 (2)	C3—C20—H20B	109.5
N3—C8—C7	123.5 (2)	H20D—C20—H20B	109.5
N2—C9—N3	110.8 (2)	H20A—C20—H20B	109.5
C8—N1—N2—C9	−1.1 (3)	C10—S1—C9—N2	154.0 (2)
C9—N3—N4—C11	30.0 (3)	C10—S1—C9—N3	−28.0 (2)
C8—N3—N4—C11	−167.4 (2)	C9—S1—C10—C11	54.13 (18)
C13—O2—N5—N6	0.0 (2)	N3—N4—C11—C12	−171.17 (19)
O2—N5—N6—C12	0.0 (3)	N3—N4—C11—C10	7.4 (3)
O2—N5—N6—C14	176.97 (18)	S1—C10—C11—N4	−52.4 (3)
C6—C1—C2—C3	0.4 (4)	S1—C10—C11—C12	126.2 (2)
C1—C2—C3—C4	0.1 (4)	N5—N6—C12—C13	0.0 (3)
C1—C2—C3—C20	179.9 (3)	C14—N6—C12—C13	−176.4 (2)
C2—C3—C4—C5	−0.6 (4)	N5—N6—C12—C11	170.7 (2)
C20—C3—C4—C5	179.6 (3)	C14—N6—C12—C11	−5.7 (4)
C3—C4—C5—C6	0.7 (4)	N4—C11—C12—N6	16.6 (4)
C7—O1—C6—C5	−0.8 (4)	C10—C11—C12—N6	−162.0 (2)
C7—O1—C6—C1	179.2 (2)	N4—C11—C12—C13	−174.6 (2)
C4—C5—C6—O1	179.7 (3)	C10—C11—C12—C13	6.8 (4)
C4—C5—C6—C1	−0.2 (4)	N5—O2—C13—O3	179.4 (2)
C2—C1—C6—O1	179.8 (2)	N5—O2—C13—C12	0.0 (2)
C2—C1—C6—C5	−0.3 (4)	N6—C12—C13—O3	−179.3 (3)
C6—O1—C7—C8	−176.7 (2)	C11—C12—C13—O3	9.9 (5)
N2—N1—C8—N3	1.3 (3)	N6—C12—C13—O2	0.0 (2)
N2—N1—C8—C7	176.2 (2)	C11—C12—C13—O2	−170.8 (2)
C9—N3—C8—N1	−1.1 (3)	N5—N6—C14—C19	112.8 (3)
N4—N3—C8—N1	−167.0 (2)	C12—N6—C14—C19	−70.9 (4)
C9—N3—C8—C7	−176.1 (2)	N5—N6—C14—C15	−65.3 (3)
N4—N3—C8—C7	18.0 (3)	C12—N6—C14—C15	111.1 (3)
O1—C7—C8—N1	87.1 (3)	C19—C14—C15—C16	0.3 (4)
O1—C7—C8—N3	−98.7 (3)	N6—C14—C15—C16	178.3 (2)
N1—N2—C9—N3	0.5 (3)	C14—C15—C16—C17	0.4 (4)
N1—N2—C9—S1	178.59 (18)	C15—C16—C17—C18	−0.7 (4)
C8—N3—C9—N2	0.3 (3)	C16—C17—C18—C19	0.4 (4)
N4—N3—C9—N2	165.4 (2)	C17—C18—C19—C14	0.3 (4)
C8—N3—C9—S1	−178.00 (17)	C15—C14—C19—C18	−0.7 (4)
N4—N3—C9—S1	−12.9 (3)	N6—C14—C19—C18	−178.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O3	0.97	2.27	3.041 (3)	135
C10—H10A···O3i	0.97	2.54	3.162 (3)	122
C10—H10B···O3ii	0.97	2.46	3.292 (3)	144
C19—H19A···N5iii	0.93	2.57	3.386 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O3	0.97	2.27	3.041 (3)	135
C10—H10A⋯O3i	0.97	2.54	3.162 (3)	122
C10—H10B⋯O3ii	0.97	2.46	3.292 (3)	144
C19—H19A⋯N5iii	0.93	2.57	3.386 (3)	147

Symmetry codes: (i) ; (ii) ; (iii) .