4-[3-(1-Naphthyl­oxymeth­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl]-3-p-tolyl­sydnone

Goh, J.H.; Fun, H.-K.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536810017812

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1394-o1395

https://doi.org/10.1107/S1600536810017812

Open

access

4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone

Jia Hao Goh,^a ‡ Hoong-Kun Fun,^a ^*§ Nithinchandra ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 May 2010; accepted 14 May 2010; online 22 May 2010)

In the title sydnone compound, C₂₄H₁₈N₆O₃S {systematic name: 4-[3-(1-naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-5-olate} an intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. The 3,6-dihydro-1,3,4-thiadiazine ring adopts a twist-boat conformation. The essentially planar 1,2,3-oxadiazole and 1,2,4-triazole rings [maximum deviations of 0.006 (1) and 0.008 (1) Å, respectively] are inclined to one another at interplanar angle of 44.11 (4)°. The naphthalene unit forms an interplanar angle of 66.40 (4)° with the 1,2,4-triazole ring. In the crystal packing, pairs of intermolecular C—H⋯O hydrogen bonds link adjacent molecules into dimers incorporating R₂²(12) ring motifs. Further stabilization is provided by weak C—H⋯π interactions.

Related literature

For general background to and applications of the title sydnone compound, see: Baker et al. (1949 ); Hedge et al. (2008 ); Rai et al. (2008 ). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ). For related structures, see: Baker & Ollis (1957 ); Goh et al. (2010a ,b ,c ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₄H₁₈N₆O₃S
M_r = 470.50
Monoclinic, P 2₁ /c
a = 21.6096 (8) Å
b = 8.3622 (3) Å
c = 11.9272 (4) Å
β = 94.694 (1)°
V = 2148.06 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 100 K
0.82 × 0.28 × 0.22 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.857, T_max = 0.959
30407 measured reflections
9432 independent reflections
8048 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.110
S = 1.08
9432 reflections
379 parameters
All H-atom parameters refined
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C23 and C1/C6–C10 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O3	0.973 (13)	2.401 (14)	3.0928 (10)	127.7 (10)
C14—H14B⋯O3ⁱ	0.973 (13)	2.396 (13)	3.1612 (10)	135.2 (11)
C8—H8A⋯Cg1ⁱⁱ	0.980 (17)	2.603 (17)	3.3928 (11)	138.0 (13)
C24—H24C⋯Cg2	0.993 (19)	2.95 (2)	3.7066 (14)	134.3 (17)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{3\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810017812/lh5045sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017812/lh5045Isup2.hkl

checkCIF report

Comment top

Sydnones constitute a well-defined class of mesoionic compounds consisting of 1,2,3-oxadiazole ring system. The introduction of the concept of mesoionic structure for certain heterocyclic compounds in the year 1949 has proved to be a fruitful development in heterocyclic chemistry (Baker et al., 1949). The study of sydnones still remains a field of interest because of their electronic structures and also because of the various types of biological activities displayed by some of them. Interest in sydnone derivatives has also been encouraged by the discovery that they exhibit various pharmacological activities (Hedge et al., 2008; Rai et al., 2008).

A series of triazolothiadiazines were synthesized by the condensation of 4-bromoacetyl-3-aryl sydnones with 3-aryloxymethyl-4-amino-5-mercapto-1,2,4-triazoles. 4-Bromoacetyl-3-aryl sydnones were in turn obtained by the photochemical bromination of 4-acetyl-3-aryl sydnones. 3-Aryloxymethyl-4-amino-5-mercapto-1,2,4-triazoles were prepared, starting from the potassium salt of aryloxyacetyl hydrazines with carbon disulphide in alcoholic KOH. The hydrazides were in turn prepared from the corresponding esters. These aryloxymethyl esters were prepared by the reaction of appropriately substituted phenol with ethylchloroacetate in presence of anhydrous potassium carbonate in dry acetone medium.

In the title sydnone compound, an intramolecular C14—H14B···O3 hydrogen bond (Table 1) generates a six-membered ring, producing an S(6) hydrogen bond ring motif (Fig. 1, Bernstein et al., 1995). The 3,6-dihydro-1,3,4-thiadiazine ring adopts a twist-boat conformation, with puckering parameters of Q = 0.6251 (7) Å, θ = 112.76 (6)° and φ = 142.75 (7)° (Cremer & Pople, 1975). The 1,2,3-oxadiazole (C16/C17/O2/N5/N6) and 1,2,4-triazole (C12/N1/N2/C13/N3) rings are essentially planar, with maximum deviations of 0.006 (1) and -0.008 (1) Å, respectively, at atoms C16 and N1. The interplanar angle between these two rings is 44.11 (4)°. The C18–C23 benzene ring and C1–C10 naphthalene ring system are making interplanar angles of 69.72 (4) and 66.40 (4)°, with the 1,2,3-oxadiazole and 1,2,4-triazole rings, respectively. As reported previously (Goh et al., 2010a,b), the exocyclic C17–O3 bond length [1.2126 (9) Å] of the sydnone unit is inconsistent with the formulation of Baker & Ollis (1957), which reported the delocalization of a positive charge in the 1,2,3-oxadiazole ring, and a negative charge in the exocyclic oxygen. The bond lengths and angles are within normal ranges and comparable to those reported in closely related sydnone (Goh et al., 2010a,b) and 1,2,4-triazole (Goh et al., 2010c) structures.

In the crystal packing, pairs of intermolecular C14—H14B···O3[-x, -y+2, -z+1] hydrogen bonds (Table 1) link adjacent molecules into dimers incorporating R²₂(12) ring motifs (Fig. 2, Bernstein et al., 1995). Further stabilization is provided by weak C8—H8A···Cg1 [x, -y+3/2, z-3/2] and C24—H24C···Cg2 interactions (Table 1) involving the C18-C23 (Cg1) and C1/C6-C10 (Cg2) benzene rings.

Related literature top

For general background to and applications of the title sydnone compound, see: Baker et al. (1949); Hedge et al. (2008); Rai et al. (2008). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For related structures, see: Baker & Ollis (1957); Goh et al. (2010a,b,c). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

An equimolar mixture of 3-naphthyloxymethyl-4-amino-5-mercapto-1,2,4-triazoles (0.01 mol) and 4-bromoacetyl-3-tolylsydnones (0.01 mol) in absolute ethanol was heated under reflux for 10-12 h. The solution was concentrated, cooled to room temperature and neutralized with 10 % sodium bicarbonate solution. Solid product formed was collected by filtration and recrystallized from ethanol. Single crystals for X-ray analysis were obtained from a 1:2 mixture of DMF and ethanol by slow evaporation.

Structure description top

For general background to and applications of the title sydnone compound, see: Baker et al. (1949); Hedge et al. (2008); Rai et al. (2008). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For related structures, see: Baker & Ollis (1957); Goh et al. (2010a,b,c). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

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 for non-H atoms and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis, showing adjacent molecules being linked into dimers. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

4-[3-(1-naphthyloxymethyl)-7H-1,2,4-triazolo[3,4- b][1,3,4]thiadiazin-6-yl]-3-p-tolyl-4,5-dihydro-1,2,3- oxadiazol-3-ium-5-olate top

Crystal data top

C₂₄H₁₈N₆O₃S	F(000) = 976
M_r = 470.50	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9918 reflections
a = 21.6096 (8) Å	θ = 2.6–35.1°
b = 8.3622 (3) Å	µ = 0.19 mm⁻¹
c = 11.9272 (4) Å	T = 100 K
β = 94.694 (1)°	Block, colourless
V = 2148.06 (13) Å³	0.82 × 0.28 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	9432 independent reflections
Radiation source: fine-focus sealed tube	8048 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 35.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −34→34
T_min = 0.857, T_max = 0.959	k = −13→11
30407 measured reflections	l = −19→17

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	All H-atom parameters refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0621P)² + 0.4207P] where P = (F_o² + 2F_c²)/3
9432 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₄H₁₈N₆O₃S	V = 2148.06 (13) Å³
M_r = 470.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.6096 (8) Å	µ = 0.19 mm⁻¹
b = 8.3622 (3) Å	T = 100 K
c = 11.9272 (4) Å	0.82 × 0.28 × 0.22 mm
β = 94.694 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	9432 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	8048 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.959	R_int = 0.023
30407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.110	All H-atom parameters refined
S = 1.08	Δρ_max = 0.58 e Å⁻³
9432 reflections	Δρ_min = −0.31 e Å⁻³
379 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.054237 (8)	0.64796 (2)	0.368050 (17)	0.01458 (5)
O1	0.25803 (3)	0.72732 (8)	0.06654 (5)	0.01628 (11)
O2	0.09850 (3)	1.30606 (7)	0.46932 (5)	0.01662 (11)
O3	0.00745 (3)	1.17152 (8)	0.43365 (5)	0.01799 (11)
N1	0.14829 (3)	0.50393 (9)	0.12173 (6)	0.01643 (12)
N2	0.11061 (3)	0.46927 (8)	0.20910 (6)	0.01603 (12)
N3	0.12737 (3)	0.72984 (8)	0.20468 (6)	0.01263 (11)
N4	0.13693 (3)	0.88576 (8)	0.24115 (6)	0.01300 (11)
N5	0.15806 (3)	1.29814 (8)	0.43898 (6)	0.01614 (12)
N6	0.15941 (3)	1.17335 (8)	0.37354 (5)	0.01269 (11)
C1	0.35987 (4)	0.77223 (11)	0.01602 (7)	0.01752 (14)
C2	0.38308 (4)	0.65856 (13)	0.09650 (8)	0.02498 (18)
C3	0.44556 (5)	0.62503 (19)	0.10958 (11)	0.0366 (3)
C4	0.48733 (5)	0.7049 (2)	0.04353 (11)	0.0389 (3)
C5	0.46585 (5)	0.81610 (17)	−0.03400 (10)	0.0320 (2)
C6	0.40179 (4)	0.85376 (12)	−0.05035 (8)	0.02161 (16)
C7	0.37898 (5)	0.97005 (13)	−0.12929 (8)	0.02567 (18)
C8	0.31662 (5)	0.99837 (12)	−0.14608 (8)	0.02419 (17)
C9	0.27387 (4)	0.91590 (10)	−0.08351 (7)	0.01914 (14)
C10	0.29522 (4)	0.80784 (10)	−0.00217 (7)	0.01503 (13)
C11	0.19294 (3)	0.75150 (10)	0.04109 (7)	0.01550 (13)
C12	0.15819 (3)	0.65872 (9)	0.12197 (7)	0.01378 (12)
C13	0.09846 (3)	0.60679 (9)	0.25608 (7)	0.01354 (12)
C14	0.03560 (3)	0.85027 (9)	0.31981 (7)	0.01418 (12)
C15	0.09438 (3)	0.94058 (9)	0.30182 (6)	0.01176 (11)
C16	0.10454 (3)	1.09342 (9)	0.35705 (6)	0.01216 (11)
C17	0.06224 (4)	1.18116 (9)	0.41931 (6)	0.01406 (12)
C18	0.21821 (3)	1.14204 (9)	0.32812 (6)	0.01316 (12)
C19	0.22339 (4)	1.16937 (10)	0.21476 (7)	0.01628 (13)
C20	0.28120 (4)	1.14737 (11)	0.17364 (7)	0.01943 (15)
C21	0.33262 (4)	1.10009 (11)	0.24445 (8)	0.02073 (15)
C22	0.32506 (4)	1.07116 (11)	0.35765 (8)	0.02126 (15)
C23	0.26765 (4)	1.09216 (10)	0.40109 (7)	0.01746 (14)
C24	0.39559 (5)	1.08553 (16)	0.19990 (11)	0.0326 (2)
H2A	0.3546 (7)	0.602 (2)	0.1375 (14)	0.036 (4)*
H3A	0.4629 (9)	0.548 (3)	0.1663 (17)	0.056 (5)*
H4A	0.5305 (9)	0.677 (3)	0.0521 (16)	0.053 (5)*
H5A	0.4945 (7)	0.876 (2)	−0.0788 (14)	0.033 (4)*
H7A	0.4102 (7)	1.029 (2)	−0.1753 (13)	0.035 (4)*
H8A	0.3011 (7)	1.076 (2)	−0.2028 (14)	0.038 (4)*
H9A	0.2288 (6)	0.9413 (19)	−0.0985 (11)	0.024 (3)*
H11A	0.1812 (6)	0.7163 (18)	−0.0368 (11)	0.020 (3)*
H11B	0.1818 (6)	0.8606 (17)	0.0462 (12)	0.021 (3)*
H14A	0.0118 (6)	0.8427 (17)	0.2483 (12)	0.020 (3)*
H14B	0.0114 (6)	0.8965 (17)	0.3770 (11)	0.017 (3)*
H19A	0.1867 (6)	1.1991 (18)	0.1683 (12)	0.022 (3)*
H20A	0.2844 (7)	1.1636 (18)	0.0939 (13)	0.026 (3)*
H22A	0.3595 (7)	1.039 (2)	0.4079 (12)	0.029 (4)*
H23A	0.2619 (6)	1.0695 (19)	0.4794 (12)	0.026 (3)*
H24A	0.4217 (10)	1.175 (3)	0.2286 (18)	0.059 (6)*
H24B	0.4133 (8)	0.985 (3)	0.2221 (16)	0.049 (5)*
H24C	0.3950 (8)	1.088 (3)	0.1166 (16)	0.048 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01306 (8)	0.01134 (8)	0.01984 (9)	−0.00084 (5)	0.00436 (6)	0.00005 (6)
O1	0.0125 (2)	0.0195 (3)	0.0170 (2)	0.00011 (19)	0.00242 (18)	0.0030 (2)
O2	0.0204 (2)	0.0124 (2)	0.0174 (3)	0.00013 (19)	0.00400 (19)	−0.00343 (19)
O3	0.0160 (2)	0.0173 (3)	0.0211 (3)	0.00308 (19)	0.0046 (2)	−0.0018 (2)
N1	0.0154 (3)	0.0131 (3)	0.0211 (3)	0.0009 (2)	0.0029 (2)	−0.0035 (2)
N2	0.0145 (2)	0.0116 (3)	0.0221 (3)	0.0004 (2)	0.0027 (2)	−0.0025 (2)
N3	0.0116 (2)	0.0099 (2)	0.0166 (3)	−0.00056 (18)	0.00252 (19)	−0.0028 (2)
N4	0.0138 (2)	0.0095 (2)	0.0160 (3)	−0.00074 (19)	0.0026 (2)	−0.0023 (2)
N5	0.0197 (3)	0.0124 (3)	0.0165 (3)	−0.0018 (2)	0.0026 (2)	−0.0030 (2)
N6	0.0151 (2)	0.0103 (2)	0.0127 (2)	−0.00127 (19)	0.00128 (19)	−0.00056 (19)
C1	0.0156 (3)	0.0205 (4)	0.0168 (3)	−0.0006 (3)	0.0035 (2)	0.0003 (3)
C2	0.0160 (3)	0.0350 (5)	0.0239 (4)	0.0015 (3)	0.0015 (3)	0.0093 (4)
C3	0.0175 (4)	0.0562 (8)	0.0361 (5)	0.0061 (4)	0.0015 (4)	0.0177 (5)
C4	0.0160 (4)	0.0603 (8)	0.0409 (6)	0.0026 (4)	0.0059 (4)	0.0126 (6)
C5	0.0191 (4)	0.0453 (6)	0.0330 (5)	−0.0026 (4)	0.0101 (3)	0.0052 (5)
C6	0.0192 (3)	0.0255 (4)	0.0211 (4)	−0.0014 (3)	0.0076 (3)	0.0003 (3)
C7	0.0299 (4)	0.0239 (4)	0.0250 (4)	−0.0017 (3)	0.0131 (3)	0.0031 (3)
C8	0.0317 (4)	0.0186 (4)	0.0238 (4)	0.0049 (3)	0.0116 (3)	0.0057 (3)
C9	0.0232 (3)	0.0163 (3)	0.0187 (3)	0.0054 (3)	0.0064 (3)	0.0023 (3)
C10	0.0163 (3)	0.0147 (3)	0.0145 (3)	0.0004 (2)	0.0043 (2)	−0.0007 (2)
C11	0.0135 (3)	0.0165 (3)	0.0167 (3)	0.0022 (2)	0.0025 (2)	−0.0007 (2)
C12	0.0127 (3)	0.0127 (3)	0.0161 (3)	0.0013 (2)	0.0021 (2)	−0.0032 (2)
C13	0.0108 (2)	0.0109 (3)	0.0189 (3)	−0.0006 (2)	0.0010 (2)	−0.0012 (2)
C14	0.0111 (3)	0.0116 (3)	0.0199 (3)	0.0005 (2)	0.0022 (2)	−0.0014 (2)
C15	0.0114 (2)	0.0099 (3)	0.0140 (3)	0.0004 (2)	0.0010 (2)	−0.0006 (2)
C16	0.0130 (3)	0.0099 (3)	0.0138 (3)	−0.0001 (2)	0.0023 (2)	−0.0011 (2)
C17	0.0171 (3)	0.0111 (3)	0.0142 (3)	0.0018 (2)	0.0023 (2)	−0.0007 (2)
C18	0.0131 (3)	0.0115 (3)	0.0149 (3)	−0.0018 (2)	0.0018 (2)	−0.0002 (2)
C19	0.0180 (3)	0.0167 (3)	0.0142 (3)	−0.0019 (2)	0.0018 (2)	−0.0010 (2)
C20	0.0211 (3)	0.0196 (4)	0.0182 (3)	−0.0039 (3)	0.0059 (3)	−0.0048 (3)
C21	0.0164 (3)	0.0175 (3)	0.0289 (4)	−0.0023 (3)	0.0054 (3)	−0.0079 (3)
C22	0.0153 (3)	0.0194 (4)	0.0286 (4)	−0.0002 (3)	−0.0009 (3)	0.0002 (3)
C23	0.0169 (3)	0.0162 (3)	0.0189 (3)	−0.0019 (2)	−0.0010 (2)	0.0029 (3)
C24	0.0192 (4)	0.0360 (6)	0.0440 (6)	−0.0028 (4)	0.0112 (4)	−0.0160 (5)

Geometric parameters (Å, º) top

S1—C13	1.7390 (8)	C7—C8	1.3667 (14)
S1—C14	1.8214 (8)	C7—H7A	1.028 (16)
O1—C10	1.3707 (10)	C8—C9	1.4138 (12)
O1—C11	1.4289 (9)	C8—H8A	0.980 (17)
O2—N5	1.3667 (9)	C9—C10	1.3775 (12)
O2—C17	1.4086 (10)	C9—H9A	0.998 (14)
O3—C17	1.2126 (9)	C11—C12	1.4882 (11)
N1—C12	1.3119 (10)	C11—H11A	0.988 (14)
N1—N2	1.4044 (10)	C11—H11B	0.946 (14)
N2—C13	1.3151 (10)	C14—C15	1.5080 (10)
N3—C12	1.3704 (10)	C14—H14A	0.962 (14)
N3—C13	1.3739 (10)	C14—H14B	0.974 (13)
N3—N4	1.3846 (9)	C15—C16	1.4464 (10)
N4—C15	1.2994 (9)	C16—C17	1.4272 (10)
N5—N6	1.3049 (9)	C18—C19	1.3849 (11)
N6—C16	1.3612 (9)	C18—C23	1.3860 (11)
N6—C18	1.4454 (10)	C19—C20	1.3910 (12)
C1—C2	1.4134 (13)	C19—H19A	0.962 (14)
C1—C6	1.4246 (12)	C20—C21	1.3967 (13)
C1—C10	1.4275 (11)	C20—H20A	0.969 (15)
C2—C3	1.3752 (13)	C21—C22	1.3943 (14)
C2—H2A	0.945 (17)	C21—C24	1.5058 (13)
C3—C4	1.4134 (16)	C22—C23	1.3941 (12)
C3—H3A	0.99 (2)	C22—H22A	0.954 (15)
C4—C5	1.3659 (18)	C23—H23A	0.971 (14)
C4—H4A	0.96 (2)	C24—H24A	0.98 (2)
C5—C6	1.4174 (14)	C24—H24B	0.96 (2)
C5—H5A	0.986 (16)	C24—H24C	0.993 (19)
C6—C7	1.4139 (14)

C13—S1—C14	93.58 (4)	C12—C11—H11B	108.4 (8)
C10—O1—C11	114.75 (6)	H11A—C11—H11B	107.5 (12)
N5—O2—C17	110.81 (6)	N1—C12—N3	109.94 (7)
C12—N1—N2	107.84 (6)	N1—C12—C11	127.14 (7)
C13—N2—N1	106.48 (6)	N3—C12—C11	122.76 (7)
C12—N3—C13	105.17 (6)	N2—C13—N3	110.54 (7)
C12—N3—N4	124.47 (6)	N2—C13—S1	129.92 (6)
C13—N3—N4	128.81 (6)	N3—C13—S1	119.53 (6)
C15—N4—N3	114.39 (6)	C15—C14—S1	110.06 (5)
N6—N5—O2	105.36 (6)	C15—C14—H14A	107.6 (8)
N5—N6—C16	114.66 (6)	S1—C14—H14A	107.9 (8)
N5—N6—C18	115.62 (6)	C15—C14—H14B	114.1 (8)
C16—N6—C18	129.71 (6)	S1—C14—H14B	105.4 (8)
C2—C1—C6	119.52 (8)	H14A—C14—H14B	111.6 (11)
C2—C1—C10	122.14 (8)	N4—C15—C16	118.51 (6)
C6—C1—C10	118.34 (8)	N4—C15—C14	123.04 (7)
C3—C2—C1	120.31 (9)	C16—C15—C14	118.43 (6)
C3—C2—H2A	121.0 (10)	N6—C16—C17	105.06 (6)
C1—C2—H2A	118.6 (10)	N6—C16—C15	126.71 (6)
C2—C3—C4	120.42 (11)	C17—C16—C15	127.69 (6)
C2—C3—H3A	121.6 (11)	O3—C17—O2	120.35 (7)
C4—C3—H3A	117.9 (11)	O3—C17—C16	135.53 (7)
C5—C4—C3	120.13 (10)	O2—C17—C16	104.10 (6)
C5—C4—H4A	120.8 (12)	C19—C18—C23	122.88 (7)
C3—C4—H4A	119.1 (12)	C19—C18—N6	118.68 (7)
C4—C5—C6	121.22 (9)	C23—C18—N6	118.38 (7)
C4—C5—H5A	121.1 (10)	C18—C19—C20	117.98 (7)
C6—C5—H5A	117.6 (10)	C18—C19—H19A	118.5 (8)
C7—C6—C5	121.86 (9)	C20—C19—H19A	123.5 (8)
C7—C6—C1	119.75 (8)	C19—C20—C21	121.14 (8)
C5—C6—C1	118.39 (9)	C19—C20—H20A	117.8 (9)
C8—C7—C6	120.17 (8)	C21—C20—H20A	121.0 (9)
C8—C7—H7A	121.4 (9)	C22—C21—C20	118.96 (8)
C6—C7—H7A	118.4 (9)	C22—C21—C24	120.57 (9)
C7—C8—C9	121.15 (9)	C20—C21—C24	120.44 (9)
C7—C8—H8A	119.6 (9)	C23—C22—C21	121.09 (8)
C9—C8—H8A	119.2 (9)	C23—C22—H22A	118.3 (8)
C10—C9—C8	119.73 (8)	C21—C22—H22A	120.6 (8)
C10—C9—H9A	122.1 (8)	C18—C23—C22	117.92 (8)
C8—C9—H9A	118.1 (8)	C18—C23—H23A	120.7 (8)
O1—C10—C9	124.35 (7)	C22—C23—H23A	121.4 (8)
O1—C10—C1	114.90 (7)	C21—C24—H24A	108.9 (12)
C9—C10—C1	120.74 (7)	C21—C24—H24B	109.1 (11)
O1—C11—C12	109.19 (6)	H24A—C24—H24B	111.9 (16)
O1—C11—H11A	109.2 (8)	C21—C24—H24C	114.4 (10)
C12—C11—H11A	110.5 (8)	H24A—C24—H24C	107.1 (17)
O1—C11—H11B	112.0 (8)	H24B—C24—H24C	105.4 (16)

C12—N1—N2—C13	1.48 (8)	C12—N3—C13—N2	0.23 (8)
C12—N3—N4—C15	165.86 (7)	N4—N3—C13—N2	−165.83 (7)
C13—N3—N4—C15	−30.53 (10)	C12—N3—C13—S1	179.55 (5)
C17—O2—N5—N6	−0.43 (8)	N4—N3—C13—S1	13.50 (10)
O2—N5—N6—C16	−0.38 (9)	C14—S1—C13—N2	−153.37 (8)
O2—N5—N6—C18	178.66 (6)	C14—S1—C13—N3	27.46 (6)
C6—C1—C2—C3	−0.97 (16)	C13—S1—C14—C15	−53.80 (6)
C10—C1—C2—C3	178.48 (11)	N3—N4—C15—C16	171.38 (6)
C1—C2—C3—C4	0.6 (2)	N3—N4—C15—C14	−6.97 (10)
C2—C3—C4—C5	0.0 (2)	S1—C14—C15—N4	51.78 (9)
C3—C4—C5—C6	−0.2 (2)	S1—C14—C15—C16	−126.57 (6)
C4—C5—C6—C7	179.19 (13)	N5—N6—C16—C17	1.00 (9)
C4—C5—C6—C1	−0.20 (18)	C18—N6—C16—C17	−177.88 (7)
C2—C1—C6—C7	−178.65 (9)	N5—N6—C16—C15	−171.03 (7)
C10—C1—C6—C7	1.88 (13)	C18—N6—C16—C15	10.09 (12)
C2—C1—C6—C5	0.75 (14)	N4—C15—C16—N6	−15.34 (11)
C10—C1—C6—C5	−178.72 (9)	C14—C15—C16—N6	163.09 (7)
C5—C6—C7—C8	177.25 (11)	N4—C15—C16—C17	174.40 (7)
C1—C6—C7—C8	−3.36 (15)	C14—C15—C16—C17	−7.18 (11)
C6—C7—C8—C9	1.64 (16)	N5—O2—C17—O3	−177.66 (7)
C7—C8—C9—C10	1.61 (15)	N5—O2—C17—C16	1.00 (8)
C11—O1—C10—C9	5.75 (11)	N6—C16—C17—O3	177.21 (9)
C11—O1—C10—C1	−174.30 (7)	C15—C16—C17—O3	−10.86 (15)
C8—C9—C10—O1	176.86 (8)	N6—C16—C17—O2	−1.15 (8)
C8—C9—C10—C1	−3.09 (13)	C15—C16—C17—O2	170.78 (7)
C2—C1—C10—O1	1.93 (12)	N5—N6—C18—C19	−108.58 (8)
C6—C1—C10—O1	−178.61 (7)	C16—N6—C18—C19	70.29 (11)
C2—C1—C10—C9	−178.12 (9)	N5—N6—C18—C23	68.82 (9)
C6—C1—C10—C9	1.34 (12)	C16—N6—C18—C23	−112.31 (9)
C10—O1—C11—C12	−179.64 (6)	C23—C18—C19—C20	−0.86 (12)
N2—N1—C12—N3	−1.37 (9)	N6—C18—C19—C20	176.42 (7)
N2—N1—C12—C11	−176.75 (7)	C18—C19—C20—C21	−0.37 (13)
C13—N3—C12—N1	0.74 (8)	C19—C20—C21—C22	1.50 (13)
N4—N3—C12—N1	167.57 (7)	C19—C20—C21—C24	−176.65 (9)
C13—N3—C12—C11	176.36 (7)	C20—C21—C22—C23	−1.45 (14)
N4—N3—C12—C11	−16.80 (11)	C24—C21—C22—C23	176.69 (9)
O1—C11—C12—N1	−76.16 (10)	C19—C18—C23—C22	0.90 (12)
O1—C11—C12—N3	109.01 (8)	N6—C18—C23—C22	−176.38 (7)
N1—N2—C13—N3	−1.03 (8)	C21—C22—C23—C18	0.29 (13)
N1—N2—C13—S1	179.73 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C18–C23 and C1/C6–C10 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3	0.973 (13)	2.401 (14)	3.0928 (10)	127.7 (10)
C14—H14B···O3ⁱ	0.973 (13)	2.396 (13)	3.1612 (10)	135.2 (11)
C8—H8A···Cg1ⁱⁱ	0.980 (17)	2.603 (17)	3.3928 (11)	138.0 (13)
C24—H24C···Cg2	0.993 (19)	2.95 (2)	3.7066 (14)	134.3 (17)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, −y+3/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈N₆O₃S
M_r	470.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	21.6096 (8), 8.3622 (3), 11.9272 (4)
β (°)	94.694 (1)
V (Å³)	2148.06 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.82 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.857, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	30407, 9432, 8048
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.808

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.110, 1.08
No. of reflections	9432
No. of parameters	379
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.31

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C18–C23 and C1/C6–C10 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3	0.973 (13)	2.401 (14)	3.0928 (10)	127.7 (10)
C14—H14B···O3ⁱ	0.973 (13)	2.396 (13)	3.1612 (10)	135.2 (11)
C8—H8A···Cg1ⁱⁱ	0.980 (17)	2.603 (17)	3.3928 (11)	138.0 (13)
C24—H24C···Cg2	0.993 (19)	2.95 (2)	3.7066 (14)	134.3 (17)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, −y+3/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: C-7576-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

References

Baker, W. & Ollis, W. D. (1957). Q. Rev. Chem. Soc. 11, 15–29. CrossRef CAS Web of Science Google Scholar
Baker, W., Ollis, W. D. & Poole, V. D. (1949). J. Chem. Soc. pp. 307–314. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra & Kalluraya, B. (2010a). Acta Cryst. E66, o1303. Google Scholar
Goh, J. H., Fun, H.-K., Nithinchandra & Kalluraya, B. (2010b). Acta Cryst. E66, o1225–o1226. Google Scholar
Goh, J. H., Fun, H.-K., Vinayaka, A. C. & Kalluraya, B. (2010c). Acta Cryst. E66, o1233–o1234. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hedge, J. C., Girisha, K. S., Adhikari, A. & Kalluraya, B. (2008). Eur. J. Med. Chem. 43, 2831–2834. Web of Science PubMed Google Scholar
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715–1720. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1394-o1395

https://doi.org/10.1107/S1600536810017812

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

4-[3-(1-Naphthyl­oxymeth­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl]-3-p-tolyl­sydnone

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-[3-(1-Naphthyloxymethyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-3-p-tolylsydnone