(Z)-7-[2-(4-Bromo­phen­yl)hydrazin-1-yl­idene]-6-methyl-3-(pyridin-4-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

Fun, H.-K.; Chantrapromma, S.; Bhat, M.A.; Abdel-Aziz, H.A.

doi:10.1107/S1600536812017412

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1512-o1513

doi:10.1107/S1600536812017412

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(Z)-7-[2-(4-Bromophenyl)hydrazin-1-ylidene]-6-methyl-3-(pyridin-4-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine

Hoong-Kun Fun,^a ^*‡ Suchada Chantrapromma,^b § Mashooq A. Bhat ^c and Hatem A. Abdel-Aziz ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: hkfun@usm.my

(Received 18 April 2012; accepted 19 April 2012; online 25 April 2012)

In the asymmetric unit of the title compound, C₁₆H₁₂BrN₇S, there are two crystallographically independent molecules with similar conformations. Both molecules are slightly twisted; the central 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine ring system makes dihedral angles of 9.65 (15) and 13.29 (15)° with the pyridine and benzene rings, respectively, in one molecule, whereas the corresponding values in the other molecule are 9.30 (15) and 4.84 (15)°. A weak intramolecular C—H⋯N interaction with an S(6) ring motif is observed in each molecule. In the crystal, the independent molecules are each linked through N—H⋯N hydrogen bonds and weak C—H⋯N interactions into ribbons along the c axis. The ribbons are further linked together by weak C—H⋯N, C—H⋯π and π–π [centroid–centroid distances = 3.572 (2)–3.884 (2) Å] interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For background to and the biological activity of [1,2,4]thiazolo[3,4-b][1,3,4]thiadiazine derivatives, see: Abdel-Aziz et al. (2007 ); Abdel-Wahab et al. (2009 ); Dawood et al. (2005 ); Holla et al. (2001 ); Janin (2007 ); Prasad et al. (1998 ). For the stability of the temperature controller, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₂BrN₇S
M_r = 414.30
Monoclinic, P 2₁ /c
a = 17.9868 (7) Å
b = 10.3830 (3) Å
c = 21.2154 (6) Å
β = 124.671 (2)°
V = 3258.6 (2) Å³
Z = 8
Mo Kα radiation
μ = 2.67 mm⁻¹
T = 100 K
0.19 × 0.19 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.629, T_max = 0.644
30220 measured reflections
9252 independent reflections
4788 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.112
S = 0.99
9252 reflections
453 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.87 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6A/N4A/C7A/N5A/N6A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—HN1A⋯N7Aⁱ	0.82	2.18	2.979 (4)	165
N1B—HN1B⋯N7Bⁱ	0.88	2.15	3.015 (4)	167
C1A—H1AA⋯N3A	0.95	2.40	3.022 (5)	123
C2A—H2AA⋯N5Bⁱⁱ	0.95	2.61	3.512 (4)	159
C4A—H4AA⋯N6Bⁱⁱⁱ	0.95	2.46	3.257 (5)	141
C1B—H1BA⋯N3B	0.95	2.39	3.023 (5)	123
C4B—H4BA⋯N6Aⁱⁱⁱ	0.95	2.41	3.210 (5)	142
C16A—H16B⋯N3B	0.98	2.57	3.445 (5)	149
C16A—H16C⋯Cg1^iv	0.98	2.72	3.469 (4)	133
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+2; (iv) -x+1, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: 10.1107/S1600536812017412/is5121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017412/is5121Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017412/is5121Isup3.cml

checkCIF report

Comment top

One of the most effective first-line anti-TB drugs is isoniazid (INH). Many analogues featuring the structure of INH have been synthesized and tested as antimycobacterials (Janin, 2007). On the other hand, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives have been well documented (Holla et al., 2001; Prasad et al., 1998). In continuation of our interests in the chemistry of the analogs of the title compound (Abdel-Aziz et al., 2007; Abdel-Wahab et al., 2009; Dawood et al., 2005), we reported the synthesis and crystal structure of the title compound (I).

In Fig. 1, there are two crystallographic independent molecules A and B in the asymmetric unit of (I) with differences in bond angles. The molecule of (I), C₁₆H₁₂BrN₇S, is slightly twisted. The middle 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine ring system (C6–C9/N3–N6/S1) makes the dihedral angles of 9.65 (15) and 13.29 (15)° with the pyridyl and benzene rings, respectively in molecule A whereas these values are 9.30 (15) and 4.84 (15)° in molecule B. Atoms of the 4-bromophenyl-hydrazono fragment (C10–C15/N1/N2/Br1) lie on the same plane with an r.m.s. deviation of 0.0270 (1) Å for molecule A and 0.0176 (1) Å for molecule B. In each molecule a weak intramolecular C—H···N interaction (Fig.1 and Table 1) generates an S(6) ring motif (Bernstein et al., 1995). The bond distances agree with the literature values (Allen et al., 1987).

In the crystal packing (Fig. 2), the molecules are linked into ribbons along the c axis by N—H···N hydrogen bonds together with weak C—H···N interactions (Table 1). These ribbons are further stacked along the a axis by π–π interactions with the distances of Cg2···Cg5 = 3.572 (2) Å, Cg3···Cg4^v = 3.884 (2) Å and Cg6···Cg7^iv = 3.617 (2) Å [symmetry code (v) = 1-x, 2-y, 2-z]; Cg2, Cg3, Cg4, Cg5, Cg6 and Cg7 are the centroids of C7A–C9A/N3A/N4A/S1A, C1A–C5A/N7A, C10A–C15A, C6B–C7B/N4B–N6B, C7B–C9B/N3B/N4B/S1B and C10B–C15B rings, respectively. A C—H···π interaction was presented (see Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For background to and the biological activity of [1,2,4]thiazolo[3,4-b][1,3,4]thiadiazine derivatives, see: Abdel-Aziz et al. (2007); Abdel-Wahab et al. (2009); Dawood et al. (2005); Holla et al. (2001); Janin (2007); Prasad et al. (1998). For the stability of the temperature controller, see: Cosier & Glazer (1986).

Experimental top

To a mixture of 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol (0.49 g, 2 mmol) and (Z)-N'-(4-bromophenyl)-2-oxopropanehydrazonoyl chloride (0.55 g, 2 mmol) in ethanol (30 mL), triethylamine (0.2 mL, 2 mmol) was added. The reaction mixture was heated under reflux for 3 h, then left to cool. The precipitated solid was collected by filtration, washed with ethanol, and dried. Golden block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvent at room temperature after several days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 asymmetric unit of the title compound, showing 40% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are drawn as dash lines.
	Fig. 2. A crystal packing diagram of the title compound viewed along the a axis. Hydrogen bonds are shown as dashed lines.

(Z)-7-[2-(4-Bromophenyl)hydrazin-1-ylidene]-6-methyl-3-(pyridin-4-yl)- 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine top

Crystal data top

C₁₆H₁₂BrN₇S	F(000) = 1664
M_r = 414.30	D_x = 1.689 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9252 reflections
a = 17.9868 (7) Å	θ = 1.9–30.0°
b = 10.3830 (3) Å	µ = 2.67 mm⁻¹
c = 21.2154 (6) Å	T = 100 K
β = 124.671 (2)°	Block, gold
V = 3258.6 (2) Å³	0.19 × 0.19 × 0.18 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	9252 independent reflections
Radiation source: sealed tube	4788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −24→16
T_min = 0.629, T_max = 0.644	k = −14→14
30220 measured reflections	l = −29→29

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0435P)²] where P = (F_o² + 2F_c²)/3
9252 reflections	(Δ/σ)_max = 0.002
453 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.87 e Å⁻³

Crystal data top

C₁₆H₁₂BrN₇S	V = 3258.6 (2) Å³
M_r = 414.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.9868 (7) Å	µ = 2.67 mm⁻¹
b = 10.3830 (3) Å	T = 100 K
c = 21.2154 (6) Å	0.19 × 0.19 × 0.18 mm
β = 124.671 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	9252 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4788 reflections with I > 2σ(I)
T_min = 0.629, T_max = 0.644	R_int = 0.058
30220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 0.99	Δρ_max = 0.58 e Å⁻³
9252 reflections	Δρ_min = −0.87 e Å⁻³
453 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 120.0 (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
Br1A	0.21285 (2)	−0.04237 (3)	1.17919 (2)	0.02953 (11)
S1A	0.47832 (6)	0.62207 (8)	1.11464 (5)	0.0252 (2)
N1A	0.36955 (18)	0.4220 (2)	1.11905 (15)	0.0209 (6)
HN1A	0.3936	0.4800	1.1511	0.025*
N2A	0.35167 (19)	0.4379 (2)	1.04891 (15)	0.0213 (6)
N3A	0.40347 (18)	0.6140 (3)	0.93433 (15)	0.0211 (6)
N4A	0.46926 (18)	0.7005 (3)	0.98702 (14)	0.0200 (6)
N5A	0.56814 (19)	0.8050 (3)	1.09318 (15)	0.0254 (7)
N6A	0.56960 (19)	0.8564 (3)	1.03296 (15)	0.0262 (7)
N7A	0.46123 (19)	0.9059 (3)	0.75564 (15)	0.0246 (7)
C1A	0.4377 (2)	0.7531 (3)	0.82800 (18)	0.0239 (8)
H1AA	0.4095	0.6761	0.8284	0.029*
C2A	0.4246 (2)	0.7974 (3)	0.76041 (18)	0.0255 (8)
H2AA	0.3875	0.7478	0.7152	0.031*
C3A	0.5160 (2)	0.9708 (3)	0.82084 (19)	0.0256 (8)
H3AB	0.5447	1.0462	0.8191	0.031*
C4A	0.5333 (2)	0.9342 (3)	0.89063 (19)	0.0252 (8)
H4AA	0.5725	0.9842	0.9352	0.030*
C5A	0.4928 (2)	0.8238 (3)	0.89486 (18)	0.0211 (8)
C6A	0.5110 (2)	0.7934 (3)	0.97021 (18)	0.0192 (7)
C7A	0.5078 (2)	0.7137 (3)	1.06399 (18)	0.0214 (8)
C8A	0.3948 (2)	0.5257 (3)	1.03816 (19)	0.0223 (8)
C9A	0.3703 (2)	0.5347 (3)	0.95940 (18)	0.0195 (7)
C10A	0.3285 (2)	0.3169 (3)	1.13031 (18)	0.0197 (7)
C11A	0.3397 (2)	0.3044 (3)	1.20077 (18)	0.0228 (8)
H11A	0.3716	0.3685	1.2391	0.027*
C12A	0.3042 (2)	0.1983 (3)	1.21474 (19)	0.0250 (8)
H12A	0.3118	0.1893	1.2627	0.030*
C13A	0.2580 (2)	0.1064 (3)	1.15898 (19)	0.0221 (8)
C14A	0.2448 (2)	0.1186 (3)	1.08789 (18)	0.0241 (8)
H14A	0.2121	0.0547	1.0496	0.029*
C15A	0.2797 (2)	0.2241 (3)	1.07330 (18)	0.0231 (8)
H15A	0.2705	0.2336	1.0248	0.028*
C16A	0.2991 (2)	0.4455 (3)	0.89978 (18)	0.0251 (8)
H16A	0.2913	0.4608	0.8507	0.038*
H16B	0.2419	0.4615	0.8940	0.038*
H16C	0.3178	0.3561	0.9157	0.038*
Br1B	−0.05294 (3)	−0.04795 (4)	1.15572 (2)	0.03264 (11)
S1B	0.20433 (6)	0.63491 (8)	1.09173 (4)	0.0215 (2)
N1B	0.11302 (18)	0.4113 (3)	1.10112 (15)	0.0224 (7)
HN1B	0.1418	0.4704	1.1370	0.027*
N2B	0.09887 (18)	0.4247 (2)	1.03202 (15)	0.0206 (6)
N3B	0.14408 (18)	0.6097 (3)	0.91571 (14)	0.0204 (6)
N4B	0.20336 (17)	0.7039 (2)	0.96629 (13)	0.0175 (6)
N5B	0.2957 (2)	0.8157 (3)	1.07072 (15)	0.0266 (7)
N6B	0.30106 (19)	0.8623 (3)	1.01197 (15)	0.0256 (7)
N7B	0.19972 (19)	0.9085 (3)	0.73658 (15)	0.0246 (7)
C1B	0.1683 (2)	0.7606 (3)	0.80669 (17)	0.0213 (8)
H1BA	0.1353	0.6880	0.8055	0.026*
C2B	0.1566 (2)	0.8074 (3)	0.74018 (18)	0.0228 (8)
H2BA	0.1144	0.7640	0.6936	0.027*
C3B	0.2610 (2)	0.9640 (3)	0.80338 (19)	0.0255 (8)
H3BB	0.2944	1.0345	0.8029	0.031*
C4B	0.2795 (2)	0.9255 (3)	0.87374 (18)	0.0248 (8)
H4BA	0.3248	0.9676	0.9197	0.030*
C5B	0.2301 (2)	0.8236 (3)	0.87509 (18)	0.0200 (8)
C6B	0.2458 (2)	0.7942 (3)	0.94951 (18)	0.0203 (8)
C7B	0.2370 (2)	0.7218 (3)	1.04183 (18)	0.0203 (7)
C8B	0.1359 (2)	0.5194 (3)	1.01993 (17)	0.0197 (8)
C9B	0.1158 (2)	0.5258 (3)	0.94249 (18)	0.0202 (8)
C10B	0.0730 (2)	0.3056 (3)	1.11196 (18)	0.0203 (8)
C11B	0.0878 (2)	0.2884 (3)	1.18328 (18)	0.0266 (8)
H11B	0.1244	0.3477	1.2235	0.032*
C12B	0.0489 (2)	0.1838 (3)	1.19575 (19)	0.0281 (9)
H12B	0.0590	0.1715	1.2444	0.034*
C13B	−0.0038 (2)	0.0990 (3)	1.1373 (2)	0.0247 (8)
C14B	−0.0197 (2)	0.1152 (3)	1.06614 (19)	0.0250 (8)
H14B	−0.0570	0.0560	1.0261	0.030*
C15B	0.0189 (2)	0.2178 (3)	1.05332 (19)	0.0242 (8)
H15B	0.0087	0.2286	1.0045	0.029*
C16B	0.0553 (2)	0.4243 (3)	0.88683 (18)	0.0285 (9)
H16D	0.0413	0.4447	0.8360	0.043*
H16E	−0.0008	0.4209	0.8843	0.043*
H16F	0.0858	0.3406	0.9037	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.0337 (2)	0.0289 (2)	0.0316 (2)	−0.00298 (18)	0.02195 (19)	0.00247 (17)
S1A	0.0290 (5)	0.0318 (5)	0.0180 (4)	−0.0060 (4)	0.0152 (4)	−0.0021 (4)
N1A	0.0248 (17)	0.0234 (15)	0.0168 (14)	−0.0031 (13)	0.0133 (13)	−0.0014 (11)
N2A	0.0245 (17)	0.0243 (16)	0.0159 (14)	0.0023 (13)	0.0119 (13)	0.0016 (12)
N3A	0.0201 (16)	0.0252 (16)	0.0195 (15)	−0.0024 (14)	0.0122 (13)	−0.0040 (13)
N4A	0.0198 (16)	0.0267 (15)	0.0144 (14)	0.0002 (13)	0.0103 (13)	−0.0007 (12)
N5A	0.0294 (18)	0.0316 (17)	0.0175 (15)	−0.0040 (15)	0.0148 (14)	0.0003 (13)
N6A	0.0287 (18)	0.0312 (17)	0.0186 (15)	−0.0044 (14)	0.0134 (15)	0.0008 (13)
N7A	0.0254 (18)	0.0296 (16)	0.0210 (15)	0.0036 (14)	0.0146 (14)	0.0035 (13)
C1A	0.026 (2)	0.0269 (19)	0.0203 (18)	−0.0006 (16)	0.0140 (17)	0.0012 (15)
C2A	0.020 (2)	0.035 (2)	0.0160 (18)	0.0024 (18)	0.0072 (16)	−0.0011 (16)
C3A	0.026 (2)	0.029 (2)	0.0249 (19)	−0.0016 (17)	0.0158 (17)	0.0027 (16)
C4A	0.0192 (19)	0.031 (2)	0.0198 (18)	−0.0011 (16)	0.0079 (16)	0.0012 (15)
C5A	0.0165 (19)	0.0266 (19)	0.0212 (18)	0.0062 (16)	0.0113 (16)	0.0027 (15)
C6A	0.0160 (19)	0.0242 (18)	0.0167 (17)	0.0004 (15)	0.0088 (16)	0.0000 (15)
C7A	0.022 (2)	0.0267 (18)	0.0158 (17)	0.0005 (16)	0.0107 (16)	0.0017 (15)
C8A	0.0216 (19)	0.028 (2)	0.0178 (17)	0.0022 (17)	0.0115 (16)	0.0008 (15)
C9A	0.0172 (18)	0.0246 (18)	0.0169 (17)	0.0029 (16)	0.0098 (15)	0.0011 (15)
C10A	0.0158 (18)	0.0219 (17)	0.0209 (17)	0.0024 (15)	0.0102 (16)	0.0031 (14)
C11A	0.0205 (19)	0.0308 (19)	0.0181 (17)	−0.0032 (16)	0.0116 (16)	−0.0019 (15)
C12A	0.025 (2)	0.031 (2)	0.0224 (19)	0.0028 (17)	0.0152 (17)	0.0016 (16)
C13A	0.020 (2)	0.0263 (18)	0.0213 (18)	0.0025 (16)	0.0127 (16)	0.0028 (15)
C14A	0.024 (2)	0.0242 (19)	0.0214 (18)	−0.0004 (17)	0.0110 (17)	−0.0014 (15)
C15A	0.0193 (19)	0.031 (2)	0.0185 (18)	0.0030 (17)	0.0102 (16)	0.0034 (16)
C16A	0.027 (2)	0.0300 (19)	0.0217 (18)	−0.0035 (17)	0.0162 (17)	−0.0045 (16)
Br1B	0.0373 (2)	0.0280 (2)	0.0405 (2)	−0.00200 (19)	0.0268 (2)	0.00421 (18)
S1B	0.0253 (5)	0.0267 (5)	0.0144 (4)	−0.0035 (4)	0.0124 (4)	−0.0015 (4)
N1B	0.0283 (18)	0.0259 (15)	0.0159 (15)	−0.0047 (14)	0.0143 (14)	−0.0020 (12)
N2B	0.0185 (16)	0.0257 (16)	0.0177 (15)	0.0020 (13)	0.0103 (13)	0.0016 (12)
N3B	0.0212 (16)	0.0213 (15)	0.0192 (15)	−0.0031 (13)	0.0117 (14)	−0.0046 (12)
N4B	0.0174 (15)	0.0235 (15)	0.0113 (13)	−0.0003 (13)	0.0079 (13)	0.0000 (11)
N5B	0.0315 (18)	0.0340 (17)	0.0162 (15)	−0.0068 (15)	0.0146 (14)	−0.0012 (13)
N6B	0.0284 (18)	0.0310 (16)	0.0185 (15)	−0.0072 (14)	0.0140 (14)	−0.0008 (13)
N7B	0.0292 (18)	0.0309 (16)	0.0171 (15)	0.0028 (14)	0.0151 (15)	0.0016 (13)
C1B	0.023 (2)	0.0227 (18)	0.0177 (17)	0.0019 (16)	0.0116 (16)	0.0027 (14)
C2B	0.026 (2)	0.0247 (19)	0.0165 (17)	0.0066 (17)	0.0110 (17)	0.0002 (15)
C3B	0.028 (2)	0.0287 (19)	0.0247 (19)	0.0005 (18)	0.0180 (17)	0.0041 (16)
C4B	0.022 (2)	0.034 (2)	0.0142 (17)	−0.0019 (17)	0.0085 (16)	0.0015 (15)
C5B	0.0199 (19)	0.0259 (18)	0.0144 (17)	0.0042 (16)	0.0098 (16)	0.0042 (14)
C6B	0.021 (2)	0.0224 (18)	0.0178 (17)	−0.0001 (16)	0.0112 (16)	0.0013 (15)
C7B	0.0190 (19)	0.0259 (18)	0.0167 (17)	−0.0007 (16)	0.0105 (16)	0.0010 (15)
C8B	0.0182 (18)	0.0262 (19)	0.0155 (17)	0.0019 (16)	0.0102 (15)	−0.0010 (15)
C9B	0.0198 (19)	0.0256 (19)	0.0181 (17)	0.0005 (16)	0.0125 (16)	−0.0033 (15)
C10B	0.022 (2)	0.0219 (18)	0.0221 (18)	−0.0018 (16)	0.0153 (17)	−0.0008 (15)
C11B	0.034 (2)	0.0278 (19)	0.0216 (19)	−0.0062 (18)	0.0175 (18)	−0.0042 (15)
C12B	0.033 (2)	0.034 (2)	0.0225 (19)	0.0019 (18)	0.0188 (18)	0.0031 (16)
C13B	0.022 (2)	0.0236 (18)	0.031 (2)	0.0010 (17)	0.0168 (18)	0.0042 (16)
C14B	0.022 (2)	0.0259 (19)	0.0236 (19)	−0.0023 (17)	0.0110 (17)	−0.0021 (16)
C15B	0.023 (2)	0.032 (2)	0.0195 (18)	0.0016 (17)	0.0127 (17)	0.0017 (16)
C16B	0.033 (2)	0.034 (2)	0.0200 (18)	−0.0089 (18)	0.0166 (18)	−0.0064 (15)

Geometric parameters (Å, º) top

Br1A—C13A	1.904 (3)	Br1B—C13B	1.912 (3)
S1A—C7A	1.728 (3)	S1B—C7B	1.728 (3)
S1A—C8A	1.766 (4)	S1B—C8B	1.772 (3)
N1A—N2A	1.342 (3)	N1B—N2B	1.345 (3)
N1A—C10A	1.413 (4)	N1B—C10B	1.401 (4)
N1A—HN1A	0.8231	N1B—HN1B	0.8809
N2A—C8A	1.298 (4)	N2B—C8B	1.293 (4)
N3A—C9A	1.295 (4)	N3B—C9B	1.292 (4)
N3A—N4A	1.397 (3)	N3B—N4B	1.394 (3)
N4A—C7A	1.371 (4)	N4B—C7B	1.366 (4)
N4A—C6A	1.388 (4)	N4B—C6B	1.377 (4)
N5A—C7A	1.303 (4)	N5B—C7B	1.306 (4)
N5A—N6A	1.398 (3)	N5B—N6B	1.391 (3)
N6A—C6A	1.309 (4)	N6B—C6B	1.322 (4)
N7A—C3A	1.337 (4)	N7B—C3B	1.333 (4)
N7A—C2A	1.338 (4)	N7B—C2B	1.333 (4)
C1A—C5A	1.391 (4)	C1B—C2B	1.390 (4)
C1A—C2A	1.392 (4)	C1B—C5B	1.391 (4)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.381 (4)	C3B—C4B	1.391 (4)
C3A—H3AB	0.9500	C3B—H3BB	0.9500
C4A—C5A	1.388 (4)	C4B—C5B	1.393 (4)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.472 (4)	C5B—C6B	1.469 (4)
C8A—C9A	1.469 (4)	C8B—C9B	1.469 (4)
C9A—C16A	1.501 (4)	C9B—C16B	1.493 (4)
C10A—C11A	1.396 (4)	C10B—C11B	1.391 (4)
C10A—C15A	1.397 (4)	C10B—C15B	1.396 (4)
C11A—C12A	1.387 (4)	C11B—C12B	1.396 (4)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.371 (4)	C12B—C13B	1.368 (5)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.393 (4)	C13B—C14B	1.378 (4)
C14A—C15A	1.382 (4)	C14B—C15B	1.380 (4)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9800	C16B—H16D	0.9800
C16A—H16B	0.9800	C16B—H16E	0.9800
C16A—H16C	0.9800	C16B—H16F	0.9800

C7A—S1A—C8A	98.18 (16)	C7B—S1B—C8B	97.95 (16)
N2A—N1A—C10A	117.7 (3)	N2B—N1B—C10B	117.6 (3)
N2A—N1A—HN1A	120.6	N2B—N1B—HN1B	121.6
C10A—N1A—HN1A	120.2	C10B—N1B—HN1B	120.5
C8A—N2A—N1A	119.4 (3)	C8B—N2B—N1B	119.7 (3)
C9A—N3A—N4A	117.3 (3)	C9B—N3B—N4B	117.0 (3)
C7A—N4A—C6A	104.8 (3)	C7B—N4B—C6B	105.7 (3)
C7A—N4A—N3A	129.9 (3)	C7B—N4B—N3B	129.3 (3)
C6A—N4A—N3A	125.2 (3)	C6B—N4B—N3B	124.9 (2)
C7A—N5A—N6A	106.7 (3)	C7B—N5B—N6B	106.8 (3)
C6A—N6A—N5A	108.4 (3)	C6B—N6B—N5B	108.4 (3)
C3A—N7A—C2A	116.8 (3)	C3B—N7B—C2B	115.8 (3)
C5A—C1A—C2A	118.7 (3)	C2B—C1B—C5B	117.7 (3)
C5A—C1A—H1AA	120.6	C2B—C1B—H1BA	121.2
C2A—C1A—H1AA	120.6	C5B—C1B—H1BA	121.2
N7A—C2A—C1A	123.6 (3)	N7B—C2B—C1B	125.2 (3)
N7A—C2A—H2AA	118.2	N7B—C2B—H2BA	117.4
C1A—C2A—H2AA	118.2	C1B—C2B—H2BA	117.4
N7A—C3A—C4A	123.7 (3)	N7B—C3B—C4B	124.4 (3)
N7A—C3A—H3AB	118.2	N7B—C3B—H3BB	117.8
C4A—C3A—H3AB	118.2	C4B—C3B—H3BB	117.8
C3A—C4A—C5A	119.3 (3)	C3B—C4B—C5B	118.3 (3)
C3A—C4A—H4AA	120.4	C3B—C4B—H4BA	120.8
C5A—C4A—H4AA	120.4	C5B—C4B—H4BA	120.8
C4A—C5A—C1A	117.8 (3)	C1B—C5B—C4B	118.4 (3)
C4A—C5A—C6A	116.6 (3)	C1B—C5B—C6B	125.1 (3)
C1A—C5A—C6A	125.7 (3)	C4B—C5B—C6B	116.5 (3)
N6A—C6A—N4A	109.0 (3)	N6B—C6B—N4B	108.5 (3)
N6A—C6A—C5A	123.3 (3)	N6B—C6B—C5B	122.8 (3)
N4A—C6A—C5A	127.6 (3)	N4B—C6B—C5B	128.6 (3)
N5A—C7A—N4A	111.0 (3)	N5B—C7B—N4B	110.6 (3)
N5A—C7A—S1A	124.9 (2)	N5B—C7B—S1B	124.6 (2)
N4A—C7A—S1A	124.0 (3)	N4B—C7B—S1B	124.8 (3)
N2A—C8A—C9A	115.0 (3)	N2B—C8B—C9B	115.4 (3)
N2A—C8A—S1A	121.2 (3)	N2B—C8B—S1B	121.9 (2)
C9A—C8A—S1A	123.8 (3)	C9B—C8B—S1B	122.7 (3)
N3A—C9A—C8A	126.7 (3)	N3B—C9B—C8B	127.9 (3)
N3A—C9A—C16A	114.7 (3)	N3B—C9B—C16B	114.9 (3)
C8A—C9A—C16A	118.6 (3)	C8B—C9B—C16B	117.2 (3)
C11A—C10A—C15A	120.0 (3)	C11B—C10B—C15B	119.4 (3)
C11A—C10A—N1A	118.8 (3)	C11B—C10B—N1B	118.8 (3)
C15A—C10A—N1A	121.2 (3)	C15B—C10B—N1B	121.9 (3)
C12A—C11A—C10A	119.9 (3)	C10B—C11B—C12B	120.0 (3)
C12A—C11A—H11A	120.0	C10B—C11B—H11B	120.0
C10A—C11A—H11A	120.0	C12B—C11B—H11B	120.0
C13A—C12A—C11A	119.6 (3)	C13B—C12B—C11B	119.5 (3)
C13A—C12A—H12A	120.2	C13B—C12B—H12B	120.3
C11A—C12A—H12A	120.2	C11B—C12B—H12B	120.3
C12A—C13A—C14A	121.2 (3)	C12B—C13B—C14B	121.3 (3)
C12A—C13A—Br1A	119.8 (3)	C12B—C13B—Br1B	119.4 (3)
C14A—C13A—Br1A	119.1 (3)	C14B—C13B—Br1B	119.3 (3)
C15A—C14A—C13A	119.7 (3)	C13B—C14B—C15B	119.7 (3)
C15A—C14A—H14A	120.2	C13B—C14B—H14B	120.1
C13A—C14A—H14A	120.2	C15B—C14B—H14B	120.1
C14A—C15A—C10A	119.6 (3)	C14B—C15B—C10B	120.1 (3)
C14A—C15A—H15A	120.2	C14B—C15B—H15B	119.9
C10A—C15A—H15A	120.2	C10B—C15B—H15B	119.9
C9A—C16A—H16A	109.5	C9B—C16B—H16D	109.5
C9A—C16A—H16B	109.5	C9B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C9A—C16A—H16C	109.5	C9B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5

C10A—N1A—N2A—C8A	−173.4 (3)	C10B—N1B—N2B—C8B	−178.7 (3)
C9A—N3A—N4A—C7A	2.0 (5)	C9B—N3B—N4B—C7B	−0.1 (5)
C9A—N3A—N4A—C6A	−178.9 (3)	C9B—N3B—N4B—C6B	174.5 (3)
C7A—N5A—N6A—C6A	−0.7 (4)	C7B—N5B—N6B—C6B	−0.5 (4)
C3A—N7A—C2A—C1A	2.7 (5)	C3B—N7B—C2B—C1B	2.7 (5)
C5A—C1A—C2A—N7A	−0.9 (5)	C5B—C1B—C2B—N7B	−0.2 (5)
C2A—N7A—C3A—C4A	−2.5 (5)	C2B—N7B—C3B—C4B	−2.0 (5)
N7A—C3A—C4A—C5A	0.5 (5)	N7B—C3B—C4B—C5B	−1.1 (5)
C3A—C4A—C5A—C1A	1.4 (5)	C2B—C1B—C5B—C4B	−3.0 (5)
C3A—C4A—C5A—C6A	−177.5 (3)	C2B—C1B—C5B—C6B	174.8 (3)
C2A—C1A—C5A—C4A	−1.2 (5)	C3B—C4B—C5B—C1B	3.6 (5)
C2A—C1A—C5A—C6A	177.6 (3)	C3B—C4B—C5B—C6B	−174.4 (3)
N5A—N6A—C6A—N4A	0.4 (4)	N5B—N6B—C6B—N4B	0.6 (4)
N5A—N6A—C6A—C5A	178.4 (3)	N5B—N6B—C6B—C5B	175.8 (3)
C7A—N4A—C6A—N6A	−0.1 (3)	C7B—N4B—C6B—N6B	−0.4 (4)
N3A—N4A—C6A—N6A	−179.4 (3)	N3B—N4B—C6B—N6B	−176.1 (3)
C7A—N4A—C6A—C5A	−177.9 (3)	C7B—N4B—C6B—C5B	−175.3 (3)
N3A—N4A—C6A—C5A	2.8 (5)	N3B—N4B—C6B—C5B	9.0 (5)
C4A—C5A—C6A—N6A	−7.5 (5)	C1B—C5B—C6B—N6B	−175.5 (3)
C1A—C5A—C6A—N6A	173.8 (3)	C4B—C5B—C6B—N6B	2.3 (5)
C4A—C5A—C6A—N4A	170.1 (3)	C1B—C5B—C6B—N4B	−1.3 (5)
C1A—C5A—C6A—N4A	−8.6 (5)	C4B—C5B—C6B—N4B	176.5 (3)
N6A—N5A—C7A—N4A	0.6 (4)	N6B—N5B—C7B—N4B	0.2 (4)
N6A—N5A—C7A—S1A	−178.5 (2)	N6B—N5B—C7B—S1B	−178.3 (2)
C6A—N4A—C7A—N5A	−0.4 (4)	C6B—N4B—C7B—N5B	0.1 (4)
N3A—N4A—C7A—N5A	178.9 (3)	N3B—N4B—C7B—N5B	175.5 (3)
C6A—N4A—C7A—S1A	178.8 (2)	C6B—N4B—C7B—S1B	178.6 (2)
N3A—N4A—C7A—S1A	−1.9 (5)	N3B—N4B—C7B—S1B	−5.9 (5)
C8A—S1A—C7A—N5A	179.2 (3)	C8B—S1B—C7B—N5B	−174.2 (3)
C8A—S1A—C7A—N4A	0.1 (3)	C8B—S1B—C7B—N4B	7.5 (3)
N1A—N2A—C8A—C9A	179.8 (3)	N1B—N2B—C8B—C9B	−179.7 (3)
N1A—N2A—C8A—S1A	1.4 (4)	N1B—N2B—C8B—S1B	−0.8 (4)
C7A—S1A—C8A—N2A	179.7 (3)	C7B—S1B—C8B—N2B	175.8 (3)
C7A—S1A—C8A—C9A	1.5 (3)	C7B—S1B—C8B—C9B	−5.5 (3)
N4A—N3A—C9A—C8A	0.0 (5)	N4B—N3B—C9B—C8B	2.4 (5)
N4A—N3A—C9A—C16A	179.3 (3)	N4B—N3B—C9B—C16B	−177.8 (3)
N2A—C8A—C9A—N3A	179.9 (3)	N2B—C8B—C9B—N3B	−179.8 (3)
S1A—C8A—C9A—N3A	−1.8 (5)	S1B—C8B—C9B—N3B	1.3 (5)
N2A—C8A—C9A—C16A	0.7 (5)	N2B—C8B—C9B—C16B	0.4 (4)
S1A—C8A—C9A—C16A	179.0 (2)	S1B—C8B—C9B—C16B	−178.5 (2)
N2A—N1A—C10A—C11A	−174.6 (3)	N2B—N1B—C10B—C11B	178.9 (3)
N2A—N1A—C10A—C15A	7.4 (4)	N2B—N1B—C10B—C15B	−1.1 (4)
C15A—C10A—C11A—C12A	1.5 (5)	C15B—C10B—C11B—C12B	0.1 (5)
N1A—C10A—C11A—C12A	−176.5 (3)	N1B—C10B—C11B—C12B	−179.9 (3)
C10A—C11A—C12A—C13A	−0.2 (5)	C10B—C11B—C12B—C13B	−0.1 (5)
C11A—C12A—C13A—C14A	−1.0 (5)	C11B—C12B—C13B—C14B	−0.3 (5)
C11A—C12A—C13A—Br1A	177.8 (2)	C11B—C12B—C13B—Br1B	177.5 (3)
C12A—C13A—C14A—C15A	0.8 (5)	C12B—C13B—C14B—C15B	0.8 (5)
Br1A—C13A—C14A—C15A	−178.0 (2)	Br1B—C13B—C14B—C15B	−177.1 (2)
C13A—C14A—C15A—C10A	0.6 (5)	C13B—C14B—C15B—C10B	−0.7 (5)
C11A—C10A—C15A—C14A	−1.7 (5)	C11B—C10B—C15B—C14B	0.3 (5)
N1A—C10A—C15A—C14A	176.3 (3)	N1B—C10B—C15B—C14B	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6A/N4A/C7A/N5A/N6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—HN1A···N7Aⁱ	0.82	2.18	2.979 (4)	165
N1B—HN1B···N7Bⁱ	0.88	2.15	3.015 (4)	167
C1A—H1AA···N3A	0.95	2.40	3.022 (5)	123
C2A—H2AA···N5Bⁱⁱ	0.95	2.61	3.512 (4)	159
C4A—H4AA···N6Bⁱⁱⁱ	0.95	2.46	3.257 (5)	141
C1B—H1BA···N3B	0.95	2.39	3.023 (5)	123
C4B—H4BA···N6Aⁱⁱⁱ	0.95	2.41	3.210 (5)	142
C16A—H16B···N3B	0.98	2.57	3.445 (5)	149
C16A—H16C···Cg1^iv	0.98	2.72	3.469 (4)	133

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂BrN₇S
M_r	414.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	17.9868 (7), 10.3830 (3), 21.2154 (6)
β (°)	124.671 (2)
V (Å³)	3258.6 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.67
Crystal size (mm)	0.19 × 0.19 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.629, 0.644
No. of measured, independent and observed [I > 2σ(I)] reflections	30220, 9252, 4788
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.112, 0.99
No. of reflections	9252
No. of parameters	453
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.87

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C6A/N4A/C7A/N5A/N6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—HN1A···N7Aⁱ	0.82	2.18	2.979 (4)	165
N1B—HN1B···N7Bⁱ	0.88	2.15	3.015 (4)	167
C1A—H1AA···N3A	0.95	2.40	3.022 (5)	123
C2A—H2AA···N5Bⁱⁱ	0.95	2.61	3.512 (4)	159
C4A—H4AA···N6Bⁱⁱⁱ	0.95	2.46	3.257 (5)	141
C1B—H1BA···N3B	0.95	2.39	3.023 (5)	123
C4B—H4BA···N6Aⁱⁱⁱ	0.95	2.41	3.210 (5)	142
C16A—H16B···N3B	0.98	2.57	3.445 (5)	149
C16A—H16C···Cg1^iv	0.98	2.72	3.469 (4)	133

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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Volume 68| Part 5| May 2012| Pages o1512-o1513

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

(Z)-7-[2-(4-Bromo­phen­yl)hydrazin-1-yl­­idene]-6-methyl-3-(pyridin-4-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine

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Experimental

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Data collection

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organic compounds

(Z)-7-[2-(4-Bromophenyl)hydrazin-1-ylidene]-6-methyl-3-(pyridin-4-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine