4-({[4-Amino-6-(p-bromo-benz-yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan-yl}acet-yl)-3-phenyl-sydnone.

In the title compound, C(20)H(15)BrN(6)O(4)S [symstematic name: 4-({[4-amino-6-(p-bromo-benz-yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan-yl}acet-yl)-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate], the 4,5-dihydro-1,2,4-triazine ring is essentially planar [maximum deviation = 0.020 (1) Å] and is inclined at dihedral angles of 89.06 (9), 82.21 (8) and 83.98 (8)° with respect to the oxadiazol-3-ium, phenyl and benzene rings. The oxadiazol-3-ium ring forms dihedral angles of 52.71 (9) and 8.77 (9)°, respectively, with the phenyl and benzene rings. In the crystal, the mol-ecules are linked via pairs of inter-molecular N-H⋯O hydrogen bonds, generating R(2) (2)(10) ring motifs and are further linked via inter-molecular N-H⋯N and weak C-H⋯O hydrogen bonds into infinite columns along [100].

Related literature

For general background to and the biological activity of sydnone derivatives, see: Rai et al. (2008) ▶; Jyothi et al. (2008 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H15BrN6O4S

M = 515.35

Triclinic,

a = 6.3842 (3) Å

b = 10.0832 (5) Å

c = 17.1563 (8) Å

α = 104.873 (1)°

β = 93.507 (1)°

γ = 98.189 (1)°

V = 1050.99 (9) Å3

Z = 2

Mo Kα radiation

μ = 2.10 mm−1

T = 100 K

0.32 × 0.26 × 0.06 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.553, T max = 0.892

21938 measured reflections

6161 independent reflections

5241 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.03

6161 reflections

297 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.95 e Å−3

Δρmin = −0.50 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/S1600536811010798/lh5224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010798/lh5224Isup2.hkl

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

C20H15BrN6O4S	Z = 2
Mr = 515.35	F(000) = 520
Triclinic, P1	Dx = 1.628 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3842 (3) Å	Cell parameters from 8506 reflections
b = 10.0832 (5) Å	θ = 2.5–30.1°
c = 17.1563 (8) Å	µ = 2.10 mm−1
α = 104.873 (1)°	T = 100 K
β = 93.507 (1)°	Plate, colourless
γ = 98.189 (1)°	0.32 × 0.26 × 0.06 mm
V = 1050.99 (9) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	6161 independent reflections
Radiation source: fine-focus sealed tube	5241 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 30.2°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→8
Tmin = 0.553, Tmax = 0.892	k = −14→14
21938 measured reflections	l = −24→24

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.5765P] where P = (Fo2 + 2Fc2)/3
6161 reflections	(Δ/σ)max = 0.001
297 parameters	Δρmax = 0.95 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
Br1	0.14494 (4)	0.177407 (19)	−0.446529 (11)	0.02915 (7)
S1	0.25040 (6)	0.42973 (4)	0.10384 (3)	0.01811 (9)
O1	−0.50655 (19)	0.68942 (12)	0.23590 (8)	0.0188 (2)
O2	−0.2801 (2)	0.71471 (13)	0.14077 (8)	0.0208 (3)
O3	−0.0592 (2)	0.36960 (13)	0.21831 (8)	0.0220 (3)
O4	0.3090 (2)	−0.01318 (13)	−0.08910 (8)	0.0205 (3)
N1	−0.3930 (2)	0.52932 (14)	0.27862 (9)	0.0149 (3)
N2	−0.5387 (2)	0.60958 (15)	0.28897 (9)	0.0186 (3)
N3	−0.0707 (2)	0.26436 (15)	0.00189 (9)	0.0170 (3)
N4	−0.1524 (2)	0.14792 (15)	−0.06048 (9)	0.0181 (3)
N5	0.2602 (2)	0.18642 (14)	0.00230 (9)	0.0143 (3)
N6	0.4749 (2)	0.22357 (17)	0.03542 (11)	0.0206 (3)
C1	−0.2106 (3)	0.44195 (17)	0.37978 (11)	0.0196 (3)
H1A	−0.0839	0.4967	0.3756	0.024*
C2	−0.2207 (3)	0.36200 (19)	0.43441 (11)	0.0238 (4)
H2A	−0.0994	0.3628	0.4675	0.029*
C3	−0.4115 (3)	0.28031 (19)	0.44025 (12)	0.0259 (4)
H3A	−0.4172	0.2280	0.4777	0.031*
C4	−0.5930 (3)	0.2768 (2)	0.39032 (12)	0.0248 (4)
H4A	−0.7196	0.2214	0.3940	0.030*
C5	−0.5857 (3)	0.35610 (18)	0.33486 (11)	0.0200 (3)
H5A	−0.7060	0.3541	0.3009	0.024*
C6	−0.3950 (3)	0.43812 (16)	0.33132 (10)	0.0159 (3)
C7	−0.3307 (3)	0.65627 (16)	0.19113 (10)	0.0158 (3)
C8	−0.2595 (3)	0.54977 (16)	0.22188 (10)	0.0147 (3)
C9	−0.0958 (3)	0.46663 (16)	0.19248 (10)	0.0155 (3)
C10	0.0227 (3)	0.51392 (17)	0.12772 (11)	0.0171 (3)
H10A	0.0694	0.6137	0.1461	0.021*
H10B	−0.0740	0.4948	0.0789	0.021*
C11	0.1283 (2)	0.28045 (16)	0.02926 (10)	0.0140 (3)
C12	−0.0334 (3)	0.05691 (17)	−0.09056 (10)	0.0155 (3)
C13	0.1916 (3)	0.06871 (16)	−0.06161 (10)	0.0150 (3)
C14	−0.1255 (3)	−0.06046 (17)	−0.16342 (11)	0.0186 (3)
H14A	−0.2789	−0.0807	−0.1640	0.022*
H14B	−0.0672	−0.1437	−0.1621	0.022*
C15	−0.0681 (3)	−0.01499 (16)	−0.23796 (10)	0.0169 (3)
C16	−0.1898 (3)	0.07165 (18)	−0.26599 (11)	0.0204 (3)
H16A	−0.3123	0.0922	−0.2421	0.024*
C17	−0.1300 (3)	0.12721 (18)	−0.32900 (11)	0.0229 (4)
H17A	−0.2116	0.1841	−0.3479	0.027*
C18	0.0541 (3)	0.09602 (17)	−0.36308 (11)	0.0204 (3)
C19	0.1758 (3)	0.00851 (18)	−0.33787 (11)	0.0208 (3)
H19A	0.2972	−0.0125	−0.3625	0.025*
C20	0.1132 (3)	−0.04737 (17)	−0.27502 (11)	0.0191 (3)
H20A	0.1929	−0.1067	−0.2577	0.023*
H1N6	0.538 (4)	0.226 (3)	−0.0038 (17)	0.032 (7)*
H2N6	0.512 (4)	0.153 (3)	0.0487 (14)	0.021 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.04790 (14)	0.02057 (9)	0.01944 (10)	0.00057 (8)	0.00410 (8)	0.00878 (7)
S1	0.01188 (18)	0.01887 (18)	0.0231 (2)	0.00468 (14)	0.00303 (15)	0.00339 (15)
O1	0.0194 (6)	0.0176 (5)	0.0236 (6)	0.0084 (4)	0.0060 (5)	0.0094 (5)
O2	0.0218 (6)	0.0192 (6)	0.0270 (7)	0.0074 (5)	0.0063 (5)	0.0132 (5)
O3	0.0233 (6)	0.0210 (6)	0.0275 (7)	0.0115 (5)	0.0070 (5)	0.0118 (5)
O4	0.0215 (6)	0.0212 (6)	0.0228 (6)	0.0122 (5)	0.0050 (5)	0.0075 (5)
N1	0.0147 (6)	0.0137 (6)	0.0175 (7)	0.0047 (5)	0.0021 (5)	0.0048 (5)
N2	0.0192 (7)	0.0186 (6)	0.0221 (7)	0.0086 (5)	0.0057 (6)	0.0088 (5)
N3	0.0129 (6)	0.0191 (6)	0.0196 (7)	0.0047 (5)	0.0035 (5)	0.0046 (5)
N4	0.0138 (6)	0.0205 (6)	0.0205 (7)	0.0030 (5)	0.0039 (5)	0.0060 (5)
N5	0.0105 (6)	0.0176 (6)	0.0183 (7)	0.0064 (5)	0.0035 (5)	0.0080 (5)
N6	0.0103 (6)	0.0258 (7)	0.0270 (8)	0.0081 (5)	0.0019 (6)	0.0064 (6)
C1	0.0211 (8)	0.0175 (7)	0.0207 (8)	0.0038 (6)	0.0011 (6)	0.0057 (6)
C2	0.0283 (9)	0.0234 (8)	0.0210 (8)	0.0065 (7)	−0.0025 (7)	0.0080 (7)
C3	0.0376 (11)	0.0219 (8)	0.0211 (9)	0.0050 (7)	0.0044 (8)	0.0106 (7)
C4	0.0277 (9)	0.0236 (8)	0.0236 (9)	−0.0007 (7)	0.0056 (7)	0.0093 (7)
C5	0.0203 (8)	0.0199 (7)	0.0205 (8)	0.0027 (6)	0.0028 (6)	0.0069 (6)
C6	0.0197 (8)	0.0137 (6)	0.0162 (7)	0.0049 (6)	0.0032 (6)	0.0061 (6)
C7	0.0139 (7)	0.0136 (6)	0.0207 (8)	0.0041 (5)	0.0028 (6)	0.0049 (6)
C8	0.0146 (7)	0.0135 (6)	0.0178 (7)	0.0045 (5)	0.0032 (6)	0.0058 (6)
C9	0.0140 (7)	0.0148 (7)	0.0178 (8)	0.0048 (5)	0.0014 (6)	0.0033 (6)
C10	0.0150 (7)	0.0164 (7)	0.0222 (8)	0.0066 (6)	0.0047 (6)	0.0062 (6)
C11	0.0131 (7)	0.0158 (7)	0.0162 (7)	0.0061 (5)	0.0059 (5)	0.0070 (6)
C12	0.0155 (7)	0.0175 (7)	0.0167 (7)	0.0032 (6)	0.0049 (6)	0.0094 (6)
C13	0.0168 (7)	0.0166 (7)	0.0161 (7)	0.0062 (6)	0.0050 (6)	0.0101 (6)
C14	0.0190 (8)	0.0161 (7)	0.0219 (8)	0.0021 (6)	0.0040 (6)	0.0071 (6)
C15	0.0190 (8)	0.0143 (7)	0.0177 (8)	0.0038 (6)	0.0005 (6)	0.0044 (6)
C16	0.0215 (8)	0.0188 (7)	0.0221 (8)	0.0086 (6)	0.0019 (6)	0.0047 (6)
C17	0.0310 (9)	0.0177 (7)	0.0216 (8)	0.0094 (7)	−0.0017 (7)	0.0062 (6)
C18	0.0301 (9)	0.0150 (7)	0.0158 (8)	0.0018 (6)	0.0018 (7)	0.0047 (6)
C19	0.0219 (8)	0.0216 (8)	0.0201 (8)	0.0059 (6)	0.0055 (7)	0.0056 (6)
C20	0.0217 (8)	0.0176 (7)	0.0203 (8)	0.0078 (6)	0.0021 (6)	0.0068 (6)

Br1—C18	1.9049 (18)	C3—H3A	0.9300
S1—C11	1.7508 (17)	C4—C5	1.390 (3)
S1—C10	1.8020 (16)	C4—H4A	0.9300
O1—N2	1.3680 (19)	C5—C6	1.385 (2)
O1—C7	1.429 (2)	C5—H5A	0.9300
O2—C7	1.200 (2)	C7—C8	1.428 (2)
O3—C9	1.218 (2)	C8—C9	1.465 (2)
O4—C13	1.2187 (19)	C9—C10	1.519 (2)
N1—N2	1.3088 (19)	C10—H10A	0.9700
N1—C8	1.368 (2)	C10—H10B	0.9700
N1—C6	1.445 (2)	C12—C13	1.469 (2)
N3—C11	1.300 (2)	C12—C14	1.504 (2)
N3—N4	1.381 (2)	C14—C15	1.514 (2)
N4—C12	1.300 (2)	C14—H14A	0.9700
N5—C11	1.3680 (19)	C14—H14B	0.9700
N5—C13	1.389 (2)	C15—C20	1.393 (2)
N5—N6	1.4112 (19)	C15—C16	1.401 (2)
N6—H1N6	0.81 (3)	C16—C17	1.389 (3)
N6—H2N6	0.86 (3)	C16—H16A	0.9300
C1—C2	1.383 (3)	C17—C18	1.384 (3)
C1—C6	1.389 (2)	C17—H17A	0.9300
C1—H1A	0.9300	C18—C19	1.386 (2)
C2—C3	1.394 (3)	C19—C20	1.393 (3)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.389 (3)	C20—H20A	0.9300
C11—S1—C10	99.93 (8)	C8—C9—C10	113.52 (13)
N2—O1—C7	110.81 (12)	C9—C10—S1	112.99 (11)
N2—N1—C8	114.46 (14)	C9—C10—H10A	109.0
N2—N1—C6	114.57 (14)	S1—C10—H10A	109.0
C8—N1—C6	130.92 (14)	C9—C10—H10B	109.0
N1—N2—O1	105.56 (13)	S1—C10—H10B	109.0
C11—N3—N4	118.15 (13)	H10A—C10—H10B	107.8
C12—N4—N3	120.73 (14)	N3—C11—N5	124.05 (15)
C11—N5—C13	121.19 (13)	N3—C11—S1	121.47 (12)
C11—N5—N6	116.73 (13)	N5—C11—S1	114.47 (12)
C13—N5—N6	121.61 (13)	N4—C12—C13	123.59 (15)
N5—N6—H1N6	103.2 (19)	N4—C12—C14	118.19 (15)
N5—N6—H2N6	107.7 (15)	C13—C12—C14	118.02 (14)
H1N6—N6—H2N6	103 (2)	O4—C13—N5	122.36 (15)
C2—C1—C6	118.14 (17)	O4—C13—C12	125.46 (16)
C2—C1—H1A	120.9	N5—C13—C12	112.17 (13)
C6—C1—H1A	120.9	C12—C14—C15	107.41 (13)
C1—C2—C3	120.50 (17)	C12—C14—H14A	110.2
C1—C2—H2A	119.8	C15—C14—H14A	110.2
C3—C2—H2A	119.8	C12—C14—H14B	110.2
C4—C3—C2	120.25 (18)	C15—C14—H14B	110.2
C4—C3—H3A	119.9	H14A—C14—H14B	108.5
C2—C3—H3A	119.9	C20—C15—C16	119.23 (16)
C3—C4—C5	120.06 (18)	C20—C15—C14	121.51 (15)
C3—C4—H4A	120.0	C16—C15—C14	119.03 (15)
C5—C4—H4A	120.0	C17—C16—C15	120.87 (17)
C6—C5—C4	118.46 (17)	C17—C16—H16A	119.6
C6—C5—H5A	120.8	C15—C16—H16A	119.6
C4—C5—H5A	120.8	C18—C17—C16	118.47 (16)
C5—C6—C1	122.58 (16)	C18—C17—H17A	120.8
C5—C6—N1	118.14 (15)	C16—C17—H17A	120.8
C1—C6—N1	119.16 (15)	C17—C18—C19	122.11 (17)
O2—C7—C8	136.11 (16)	C17—C18—Br1	119.06 (14)
O2—C7—O1	120.39 (14)	C19—C18—Br1	118.83 (14)
C8—C7—O1	103.49 (14)	C18—C19—C20	118.84 (16)
N1—C8—C7	105.67 (13)	C18—C19—H19A	120.6
N1—C8—C9	126.27 (14)	C20—C19—H19A	120.6
C7—C8—C9	127.67 (15)	C19—C20—C15	120.45 (16)
O3—C9—C8	122.63 (16)	C19—C20—H20A	119.8
O3—C9—C10	123.85 (15)	C15—C20—H20A	119.8
C8—N1—N2—O1	0.65 (18)	N4—N3—C11—N5	−2.7 (2)
C6—N1—N2—O1	178.30 (13)	N4—N3—C11—S1	176.05 (12)
C7—O1—N2—N1	−0.32 (17)	C13—N5—C11—N3	4.4 (2)
C11—N3—N4—C12	0.3 (2)	N6—N5—C11—N3	176.67 (16)
C6—C1—C2—C3	−0.1 (3)	C13—N5—C11—S1	−174.36 (12)
C1—C2—C3—C4	0.9 (3)	N6—N5—C11—S1	−2.14 (19)
C2—C3—C4—C5	−0.7 (3)	C10—S1—C11—N3	6.15 (16)
C3—C4—C5—C6	−0.4 (3)	C10—S1—C11—N5	−175.02 (12)
C4—C5—C6—C1	1.3 (3)	N3—N4—C12—C13	0.4 (2)
C4—C5—C6—N1	−174.73 (16)	N3—N4—C12—C14	−174.35 (15)
C2—C1—C6—C5	−1.1 (3)	C11—N5—C13—O4	176.57 (15)
C2—C1—C6—N1	174.91 (15)	N6—N5—C13—O4	4.7 (2)
N2—N1—C6—C5	51.6 (2)	C11—N5—C13—C12	−3.4 (2)
C8—N1—C6—C5	−131.18 (18)	N6—N5—C13—C12	−175.22 (15)
N2—N1—C6—C1	−124.54 (17)	N4—C12—C13—O4	−178.76 (17)
C8—N1—C6—C1	52.6 (2)	C14—C12—C13—O4	−4.1 (2)
N2—O1—C7—O2	179.06 (15)	N4—C12—C13—N5	1.2 (2)
N2—O1—C7—C8	−0.09 (17)	C14—C12—C13—N5	175.89 (14)
N2—N1—C8—C7	−0.71 (19)	N4—C12—C14—C15	92.39 (18)
C6—N1—C8—C7	−177.89 (16)	C13—C12—C14—C15	−82.61 (17)
N2—N1—C8—C9	−173.89 (15)	C12—C14—C15—C20	93.65 (18)
C6—N1—C8—C9	8.9 (3)	C12—C14—C15—C16	−80.78 (19)
O2—C7—C8—N1	−178.5 (2)	C20—C15—C16—C17	−1.1 (3)
O1—C7—C8—N1	0.44 (17)	C14—C15—C16—C17	173.41 (16)
O2—C7—C8—C9	−5.4 (3)	C15—C16—C17—C18	−0.6 (3)
O1—C7—C8—C9	173.50 (15)	C16—C17—C18—C19	1.9 (3)
N1—C8—C9—O3	−1.7 (3)	C16—C17—C18—Br1	−177.44 (13)
C7—C8—C9—O3	−173.40 (16)	C17—C18—C19—C20	−1.4 (3)
N1—C8—C9—C10	178.64 (15)	Br1—C18—C19—C20	177.91 (13)
C7—C8—C9—C10	6.9 (2)	C18—C19—C20—C15	−0.4 (3)
O3—C9—C10—S1	−9.0 (2)	C16—C15—C20—C19	1.6 (3)
C8—C9—C10—S1	170.66 (11)	C14—C15—C20—C19	−172.79 (16)
C11—S1—C10—C9	87.24 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H1N6···N3i	0.81 (3)	2.47 (3)	2.9835 (19)	123 (2)
N6—H1N6···N4i	0.81 (3)	2.40 (3)	3.050 (2)	138 (3)
N6—H2N6···O4ii	0.86 (3)	2.15 (3)	2.989 (2)	164 (2)
C14—H14B···O3iii	0.97	2.50	3.416 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H1N6⋯N3i	0.81 (3)	2.47 (3)	2.9835 (19)	123 (2)
N6—H1N6⋯N4i	0.81 (3)	2.40 (3)	3.050 (2)	138 (3)
N6—H2N6⋯O4ii	0.86 (3)	2.15 (3)	2.989 (2)	164 (2)
C14—H14B⋯O3iii	0.97	2.50	3.416 (2)	157

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