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organic compounds
2-Benzoylamino-N-[5-(4-bromophenyl)-1,3,4-thiadiazol-2-yl]ethanamide
aState Key Laboratory of Food Science and Technology, Nanchang University, 330047 Nanchang, JiangXi, People's Republic of China, and bDepartment of Pharmacy, NanChang University Medical College, 330006 Nanchang, JiangXi, People's Republic of China
*Correspondence e-mail: [email protected]
In the structure of the title compound, C17H13BrN4O2S, the dihedral angle between the two benzene rings is 38.5 (1)°; the angle between the 4-bromobenzene and thiadiazole rings is 1.3 (1)°. The conformations of the N—H and C=O bonds are anti with respect to each other. The structure displays intermolecular N—H⋯O and C—H⋯O hydrogen bonding, with both interactions leading to inversion dimers.
Related literature
For 1,3,4-thiadiazole scaffold compounds and their biological activity, see: Tu et al. (2008). For the synthesis, see: Foroumadi et al. (1999
); Levy & Palmer (1942
); Song et al. (1992
). For related structures, see: Gowda et al. (2008
); Li, Huang et al. (2008
); Li, Li et al. (2008
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: APEX2 (Bruker, 2004
); software used to prepare material for publication: APEX2 (Bruker, 2004
) and publCIF (Westrip, 2009
).
Supporting information
10.1107/S160053680900124X/wn2304sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680900124X/wn2304Isup2.hkl
N,N-Dicyclohexylcarbodiimide (5.7 mmol) was added to a cooled solution of N-benzoylglycine (5.6 mmol) and N-hydroxysuccinimide (5.6 mmol) in freshly distilled dioxane (30 ml). The reaction mixture was stirred overnight at room temperature. The insoluble material was filtered off and washed with cold dioxane. 2-Amino-5-(4-bromophenyl)-1,3,4-thiadiazole (5.5 mmol) was added to the filtrate and the reaction mixture was stirred for 48 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and the insoluble material was filtered off. The filtrate was washed successively with saturated Na2CO3 solution (20 ml, x 3), water (20 ml, x 1), 0.1 M HCl (20 ml, x 3) and water (20 ml, x 1). The organic layer evaporated in vacuo, and the residue was recrystallized from methanol. Colorless block-shaped single crystals of the title compound suitable for X-ray
precipitated after several days.Yield: 37.0%; mp: 271–273°C.H atoms were positioned geometrically and refined using a riding model; Csp2—H = 0.93 Å, Csp3—H = 0.97 Å and N—H = 0.86 Å; Uĩso(H) = 1.2 Ueq(C,N). We made several attempts to obtain better quality data for this structure. However, due to poor crystal quality and possible disorder, the R and wR values are high. The maximum residual electron density occurs 1.23 Å from atom Br1, and the minimum residual electron density is located 1.29 Å from atom Br1.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: APEX2 (Bruker, 2004); software used to prepare material for publication: APEX2 (Bruker, 2004) and publCIF (Westrip, 2009).C17H13BrN4O2S | Z = 2 |
Mr = 417.28 | F(000) = 420.0 |
Triclinic, P1 | Dx = 1.700 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.020 (4) Å | Cell parameters from 1179 reflections |
b = 13.706 (9) Å | θ = 2.6–23.7° |
c = 16.210 (5) Å | µ = 2.67 mm−1 |
α = 113.334 (17)° | T = 298 K |
β = 94.018 (19)° | Block, colourless |
γ = 92.78 (2)° | 0.54 × 0.17 × 0.04 mm |
V = 815.2 (10) Å3 |
Bruker X8 APEXII diffractometer | 2592 independent reflections |
Radiation source: fine-focus sealed tube | 1097 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −4→4 |
Tmin = 0.591, Tmax = 0.914 | k = −16→16 |
4633 measured reflections | l = −19→19 |
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)] = 0.109 | H-atom parameters constrained |
wR(F2) = 0.281 | w = 1/[σ2(Fo2) + (0.1951P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.82 | (Δ/σ)max = 0.019 |
2592 reflections | Δρmax = 1.67 e Å−3 |
227 parameters | Δρmin = −1.40 e Å−3 |
6 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (2) |
C17H13BrN4O2S | γ = 92.78 (2)° |
Mr = 417.28 | V = 815.2 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 4.020 (4) Å | Mo Kα radiation |
b = 13.706 (9) Å | µ = 2.67 mm−1 |
c = 16.210 (5) Å | T = 298 K |
α = 113.334 (17)° | 0.54 × 0.17 × 0.04 mm |
β = 94.018 (19)° |
Bruker X8 APEXII diffractometer | 2592 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 1097 reflections with I > 2σ(I) |
Tmin = 0.591, Tmax = 0.914 | Rint = 0.082 |
4633 measured reflections |
R[F2 > 2σ(F2)] = 0.109 | 6 restraints |
wR(F2) = 0.281 | H-atom parameters constrained |
S = 0.82 | Δρmax = 1.67 e Å−3 |
2592 reflections | Δρmin = −1.40 e Å−3 |
227 parameters |
Experimental. 1H-NMR (DMSO-d6): δ 4.24–4.25(d, J=5.08 Hz, 2H), 7.49–7.57 (m, 3H),7.73–7.75 (d, J=8.04 Hz, 2H), 7.89–7.91(t, J=3.60 Hz, 4H), 9.01 (s, 1H),12.91 (s, 1H). ESI-MS: m/z [M+H]+ 417.3. |
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 > σ(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 | 0.19570 (14) | 0.16142 (4) | 0.64242 (3) | 0.07526 (19) | |
S1 | 0.3284 (3) | 0.41677 (8) | 0.33059 (7) | 0.0550 (4) | |
O1 | 0.2257 (8) | 0.6333 (2) | −0.00717 (17) | 0.0636 (9) | |
O2 | 0.2253 (9) | 0.5689 (2) | 0.25867 (18) | 0.0687 (8) | |
N1 | 0.2711 (9) | 0.6635 (2) | 0.1388 (2) | 0.0551 (12) | |
H1A | 0.2352 | 0.7034 | 0.1931 | 0.066* | |
N3 | 0.5949 (10) | 0.2787 (3) | 0.1998 (2) | 0.0621 (13) | |
N4 | 0.5645 (10) | 0.2351 (2) | 0.2632 (2) | 0.0597 (8) | |
N2 | 0.4834 (9) | 0.4276 (2) | 0.1728 (2) | 0.0539 (8) | |
H2A | 0.5726 | 0.3992 | 0.1229 | 0.065* | |
C4 | −0.2078 (13) | 0.9136 (3) | 0.0368 (3) | 0.0711 (18) | |
H4B | −0.3108 | 0.9254 | −0.0112 | 0.085* | |
C5 | −0.0907 (12) | 0.8176 (3) | 0.0241 (3) | 0.0610 (16) | |
H5A | −0.1231 | 0.7628 | −0.0332 | 0.073* | |
C10 | 0.4756 (11) | 0.3703 (3) | 0.2263 (3) | 0.0512 (11) | |
C16 | 0.1797 (12) | 0.3039 (3) | 0.5556 (3) | 0.0632 (17) | |
H16A | 0.0838 | 0.3486 | 0.6061 | 0.076* | |
C15 | 0.2691 (13) | 0.2067 (3) | 0.5481 (3) | 0.0603 (10) | |
C12 | 0.3711 (10) | 0.2674 (3) | 0.4098 (2) | 0.0471 (9) | |
C14 | 0.4058 (11) | 0.1370 (3) | 0.4729 (3) | 0.0598 (11) | |
H14A | 0.4596 | 0.0701 | 0.4688 | 0.072* | |
C17 | 0.2354 (12) | 0.3345 (3) | 0.4857 (3) | 0.0587 (11) | |
H17A | 0.1807 | 0.4014 | 0.4900 | 0.070* | |
C8 | 0.4114 (12) | 0.5638 (3) | 0.1200 (3) | 0.0560 (15) | |
H8A | 0.6486 | 0.5723 | 0.1144 | 0.067* | |
H8B | 0.3068 | 0.5116 | 0.0627 | 0.067* | |
C9 | 0.3647 (11) | 0.5237 (3) | 0.1913 (2) | 0.0475 (10) | |
C11 | 0.4297 (11) | 0.2963 (3) | 0.3341 (2) | 0.0483 (10) | |
C13 | 0.4598 (12) | 0.1698 (3) | 0.4041 (3) | 0.0601 (16) | |
H13A | 0.5571 | 0.1253 | 0.3537 | 0.072* | |
C7 | 0.1970 (11) | 0.6938 (3) | 0.0722 (3) | 0.0521 (13) | |
C6 | 0.0730 (11) | 0.7991 (3) | 0.0926 (2) | 0.0489 (14) | |
C2 | −0.0154 (12) | 0.9776 (3) | 0.1919 (3) | 0.0601 (16) | |
H2B | 0.0074 | 1.0320 | 0.2494 | 0.072* | |
C3 | −0.1698 (12) | 0.9930 (3) | 0.1230 (3) | 0.0643 (17) | |
H3B | −0.2533 | 1.0585 | 0.1332 | 0.077* | |
C1 | 0.1113 (12) | 0.8805 (3) | 0.1780 (3) | 0.0555 (15) | |
H1B | 0.2216 | 0.8701 | 0.2259 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0941 (4) | 0.0888 (3) | 0.0604 (2) | 0.0226 (3) | 0.0361 (2) | 0.04206 (19) |
S1 | 0.0804 (8) | 0.0441 (5) | 0.0406 (5) | 0.0193 (5) | 0.0286 (5) | 0.0118 (4) |
O1 | 0.106 (2) | 0.0501 (14) | 0.0414 (6) | 0.0279 (14) | 0.0433 (10) | 0.0174 (7) |
O2 | 0.1043 (12) | 0.0616 (16) | 0.0469 (7) | 0.0256 (13) | 0.0439 (6) | 0.0207 (9) |
N1 | 0.082 (3) | 0.0452 (17) | 0.0435 (16) | 0.0255 (16) | 0.0332 (18) | 0.0165 (13) |
N3 | 0.099 (3) | 0.0488 (17) | 0.0448 (17) | 0.0288 (18) | 0.0270 (19) | 0.0193 (13) |
N4 | 0.1059 (15) | 0.0386 (15) | 0.0399 (8) | 0.0252 (12) | 0.0297 (7) | 0.0154 (8) |
N2 | 0.075 (2) | 0.0474 (5) | 0.0474 (5) | 0.0157 (15) | 0.0353 (16) | 0.0212 (3) |
C4 | 0.097 (4) | 0.049 (2) | 0.070 (3) | 0.025 (2) | 0.022 (3) | 0.022 (2) |
C5 | 0.080 (3) | 0.042 (2) | 0.053 (2) | 0.012 (2) | 0.009 (2) | 0.0102 (18) |
C10 | 0.073 (3) | 0.0390 (7) | 0.0442 (7) | 0.0091 (19) | 0.024 (2) | 0.0156 (4) |
C16 | 0.080 (3) | 0.054 (2) | 0.051 (2) | 0.012 (2) | 0.034 (2) | 0.0102 (19) |
C15 | 0.0825 (16) | 0.0564 (19) | 0.0442 (9) | −0.0018 (12) | 0.0194 (8) | 0.0211 (8) |
C12 | 0.0546 (15) | 0.0498 (18) | 0.0351 (9) | 0.0036 (12) | 0.0172 (7) | 0.0131 (8) |
C14 | 0.066 (2) | 0.066 (2) | 0.0600 (12) | 0.0136 (14) | 0.0282 (10) | 0.0337 (10) |
C17 | 0.078 (2) | 0.050 (2) | 0.0448 (11) | 0.0131 (15) | 0.0261 (10) | 0.0109 (10) |
C8 | 0.064 (3) | 0.061 (2) | 0.053 (2) | 0.026 (2) | 0.035 (2) | 0.0269 (16) |
C9 | 0.0644 (16) | 0.041 (2) | 0.0353 (8) | 0.0082 (16) | 0.0210 (7) | 0.0104 (12) |
C11 | 0.0753 (18) | 0.0407 (18) | 0.0336 (10) | 0.0106 (14) | 0.0223 (9) | 0.0165 (9) |
C13 | 0.094 (3) | 0.042 (2) | 0.046 (2) | 0.010 (2) | 0.030 (2) | 0.0159 (16) |
C7 | 0.071 (3) | 0.047 (2) | 0.0344 (7) | 0.0104 (19) | 0.0185 (14) | 0.0105 (9) |
C6 | 0.061 (3) | 0.047 (2) | 0.0339 (18) | 0.0118 (19) | 0.030 (2) | 0.0067 (16) |
C2 | 0.078 (3) | 0.043 (2) | 0.050 (2) | 0.009 (2) | 0.019 (2) | 0.0062 (18) |
C3 | 0.080 (3) | 0.052 (2) | 0.065 (3) | 0.031 (2) | 0.025 (3) | 0.0211 (19) |
C1 | 0.071 (3) | 0.047 (2) | 0.046 (2) | 0.016 (2) | 0.023 (2) | 0.0120 (17) |
Br1—C15 | 1.898 (5) | C16—C17 | 1.382 (7) |
S1—C10 | 1.714 (4) | C16—H16A | 0.9300 |
S1—C11 | 1.741 (5) | C15—C14 | 1.387 (6) |
O1—C7 | 1.242 (4) | C12—C13 | 1.370 (6) |
O2—C9 | 1.214 (5) | C12—C17 | 1.380 (5) |
N1—C7 | 1.323 (6) | C12—C11 | 1.461 (6) |
N1—C8 | 1.430 (5) | C14—C13 | 1.383 (7) |
N1—H1A | 0.8600 | C14—H14A | 0.9300 |
N3—C10 | 1.285 (5) | C17—H17A | 0.9300 |
N3—N4 | 1.387 (6) | C8—C9 | 1.483 (7) |
N4—C11 | 1.299 (5) | C8—H8A | 0.9700 |
N2—C9 | 1.349 (5) | C8—H8B | 0.9700 |
N2—C10 | 1.381 (6) | C13—H13A | 0.9300 |
N2—H2A | 0.8600 | C7—C6 | 1.469 (6) |
C4—C5 | 1.361 (7) | C6—C1 | 1.383 (5) |
C4—C3 | 1.382 (6) | C2—C3 | 1.335 (7) |
C4—H4B | 0.9300 | C2—C1 | 1.388 (6) |
C5—C6 | 1.367 (7) | C2—H2B | 0.9300 |
C5—H5A | 0.9300 | C3—H3B | 0.9300 |
C16—C15 | 1.359 (7) | C1—H1B | 0.9300 |
C10—S1—C11 | 86.0 (2) | C16—C17—H17A | 119.5 |
C7—N1—C8 | 119.6 (3) | N1—C8—C9 | 112.3 (3) |
C7—N1—H1A | 120.2 | N1—C8—H8A | 109.1 |
C8—N1—H1A | 120.2 | C9—C8—H8A | 109.1 |
C10—N3—N4 | 110.7 (4) | N1—C8—H8B | 109.1 |
C11—N4—N3 | 113.3 (3) | C9—C8—H8B | 109.1 |
C9—N2—C10 | 126.3 (3) | H8A—C8—H8B | 107.9 |
C9—N2—H2A | 116.8 | O2—C9—N2 | 121.9 (4) |
C10—N2—H2A | 116.8 | O2—C9—C8 | 125.0 (4) |
C5—C4—C3 | 118.3 (5) | N2—C9—C8 | 113.1 (3) |
C5—C4—H4B | 120.9 | N4—C11—C12 | 123.3 (4) |
C3—C4—H4B | 120.9 | N4—C11—S1 | 113.4 (3) |
C4—C5—C6 | 122.2 (4) | C12—C11—S1 | 123.3 (3) |
C4—C5—H5A | 118.9 | C12—C13—C14 | 120.4 (4) |
C6—C5—H5A | 118.9 | C12—C13—H13A | 119.8 |
N3—C10—N2 | 119.8 (4) | C14—C13—H13A | 119.8 |
N3—C10—S1 | 116.5 (4) | O1—C7—N1 | 120.5 (4) |
N2—C10—S1 | 123.6 (3) | O1—C7—C6 | 120.0 (4) |
C15—C16—C17 | 118.0 (4) | N1—C7—C6 | 119.4 (3) |
C15—C16—H16A | 121.0 | C5—C6—C1 | 118.3 (4) |
C17—C16—H16A | 121.0 | C5—C6—C7 | 118.5 (3) |
C16—C15—C14 | 122.6 (5) | C1—C6—C7 | 123.2 (4) |
C16—C15—Br1 | 119.4 (3) | C3—C2—C1 | 120.2 (4) |
C14—C15—Br1 | 118.0 (4) | C3—C2—H2B | 119.9 |
C13—C12—C17 | 119.7 (4) | C1—C2—H2B | 119.9 |
C13—C12—C11 | 117.6 (3) | C2—C3—C4 | 121.2 (4) |
C17—C12—C11 | 122.6 (4) | C2—C3—H3B | 119.4 |
C13—C14—C15 | 118.2 (4) | C4—C3—H3B | 119.4 |
C13—C14—H14A | 120.9 | C6—C1—C2 | 119.8 (4) |
C15—C14—H14A | 120.9 | C6—C1—H1B | 120.1 |
C12—C17—C16 | 121.0 (4) | C2—C1—H1B | 120.1 |
C12—C17—H17A | 119.5 | ||
C10—N3—N4—C11 | −1.0 (5) | C13—C12—C11—N4 | −0.9 (6) |
C3—C4—C5—C6 | −2.5 (8) | C17—C12—C11—N4 | 178.3 (4) |
N4—N3—C10—N2 | 179.7 (4) | C13—C12—C11—S1 | 179.6 (3) |
N4—N3—C10—S1 | 2.2 (5) | C17—C12—C11—S1 | −1.2 (6) |
C9—N2—C10—N3 | 179.2 (4) | C10—S1—C11—N4 | 1.5 (3) |
C9—N2—C10—S1 | −3.6 (6) | C10—S1—C11—C12 | −178.9 (4) |
C11—S1—C10—N3 | −2.2 (4) | C17—C12—C13—C14 | 1.8 (6) |
C11—S1—C10—N2 | −179.5 (4) | C11—C12—C13—C14 | −179.0 (4) |
C17—C16—C15—C14 | −1.5 (7) | C15—C14—C13—C12 | −1.8 (7) |
C17—C16—C15—Br1 | −179.8 (3) | C8—N1—C7—O1 | 5.2 (6) |
C16—C15—C14—C13 | 1.7 (7) | C8—N1—C7—C6 | −176.1 (4) |
Br1—C15—C14—C13 | −179.9 (3) | C4—C5—C6—C1 | 1.8 (7) |
C13—C12—C17—C16 | −1.6 (6) | C4—C5—C6—C7 | −178.7 (5) |
C11—C12—C17—C16 | 179.2 (4) | O1—C7—C6—C5 | 17.2 (7) |
C15—C16—C17—C12 | 1.4 (7) | N1—C7—C6—C5 | −161.5 (4) |
C7—N1—C8—C9 | −159.0 (4) | O1—C7—C6—C1 | −163.3 (4) |
C10—N2—C9—O2 | −2.3 (6) | N1—C7—C6—C1 | 18.0 (7) |
C10—N2—C9—C8 | −180.0 (4) | C1—C2—C3—C4 | 0.1 (8) |
N1—C8—C9—O2 | −0.2 (6) | C5—C4—C3—C2 | 1.6 (8) |
N1—C8—C9—N2 | 177.4 (3) | C5—C6—C1—C2 | 0.0 (7) |
N3—N4—C11—C12 | 179.8 (4) | C7—C6—C1—C2 | −179.5 (4) |
N3—N4—C11—S1 | −0.6 (5) | C3—C2—C1—C6 | −0.9 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O2i | 0.93 | 2.49 | 3.400 (5) | 168 |
N2—H2A···O1ii | 0.86 | 1.99 | 2.835 (5) | 167 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H13BrN4O2S |
Mr | 417.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 4.020 (4), 13.706 (9), 16.210 (5) |
α, β, γ (°) | 113.334 (17), 94.018 (19), 92.78 (2) |
V (Å3) | 815.2 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.67 |
Crystal size (mm) | 0.54 × 0.17 × 0.04 |
Data collection | |
Diffractometer | Bruker X8 APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.591, 0.914 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4633, 2592, 1097 |
Rint | 0.082 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.109, 0.281, 0.82 |
No. of reflections | 2592 |
No. of parameters | 227 |
No. of restraints | 6 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.67, −1.40 |
Computer programs: , SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), APEX2 (Bruker, 2004) and publCIF (Westrip, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O2i | 0.93 | 2.49 | 3.400 (5) | 167.6 |
N2—H2A···O1ii | 0.86 | 1.99 | 2.835 (5) | 166.8 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
Footnotes
‡Additional correspondence author, e-mail: [email protected].
Acknowledgements
The work was supported by the Science and Technology Research Project of JiangXi Provincial Educational Department (No. GJJ09076), the Science and Technology Planning Project of JiangXi Provincial Health Department (No. 20082015) and the Natural Science Foundation of JiangXi Province, China.
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In our previous work, 1,3,4-thiadiazole scaffold compounds and their biological activity have been studied (Tu et al., 2008). In view of the importance of these organic materials, the title compound (Fig. 1) was synthesized (Foroumadi et al., 1999; Levy & Palmer 1942; Song et al., 1992) and its crystal structure is reported here.
In the structure of the title compound, C17H13BrN4O2S, the dihedral angle between the p-bromobenzene and thiadiazole rings is 1.3 (1)°; the angle between the two benzene rings is 38.5 (1)°. The conformations of the N—H and C═O bonds are anti with respect to each other. Bond lengths and angles are in normal ranges and comparable to those in related structures (Gowda et al., 2008; Li, Huang et al., 2008; Li, Li et al., 2008). In the crystal structure, molecules are linked through intermolecular C—H···O and N—H···O hydrogen bonds, forming a three-dimensional network (Table 1, Figure 2).