Literature DB >> 21581930

2-Benzoyl-amino-N-[5-(4-bromo-phen-yl)-1,3,4-thia-diazol-2-yl]ethanamide.

Hui-Ming Huang, Shi-Yuan Luo, Shao-Hua Li, Cheng-Mei Liu, Guo-Gang Tu.   

Abstract

In the structure of the title compound, C(17)H(13)BrN(4)O(2)S, the dihedral angle between the two benzene rings is 38.5 (1)°; the angle between the 4-bromo-benzene and thia-diazole 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 inter-molecular N-H⋯O and C-H⋯O hydrogen bonding, with both interactions leading to inversion dimers.

Entities:  

Year:  2009        PMID： 21581930      PMCID： PMC2968191          DOI： 10.1107/S160053680900124X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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

C17H13BrN4O2S M = 417.28 Triclinic, a = 4.020 (4) Å b = 13.706 (9) Å c = 16.210 (5) Å α = 113.334 (17)° β = 94.018 (19)° γ = 92.78 (2)° V = 815.2 (10) Å3 Z = 2 Mo Kα radiation μ = 2.67 mm−1 T = 298 (2) K 0.54 × 0.17 × 0.04 mm

Data collection

Bruker X8 APEXII diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.591, T max = 0.914 4633 measured reflections 2592 independent reflections 1097 reflections with I > 2σ(I) R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.109 wR(F 2) = 0.281 S = 0.82 2592 reflections 227 parameters 6 restraints H-atom parameters constrained Δρmax = 1.67 e Å−3 Δρmin = −1.40 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900124X/wn2304sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680900124X/wn2304Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H13BrN4O2SZ = 2
Mr = 417.28F(000) = 420.0
Triclinic, P1Dx = 1.700 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 4.020 (4) ÅCell parameters from 1179 reflections
b = 13.706 (9) Åθ = 2.6–23.7°
c = 16.210 (5) ŵ = 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 diffractometer2592 independent reflections
Radiation source: fine-focus sealed tube1097 reflections with I > 2σ(I)
graphiteRint = 0.082
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −4→4
Tmin = 0.591, Tmax = 0.914k = −16→16
4633 measured reflectionsl = −19→19
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.109H-atom parameters constrained
wR(F2) = 0.281w = 1/[σ2(Fo2) + (0.1951P)2] where P = (Fo2 + 2Fc2)/3
S = 0.82(Δ/σ)max = 0.019
2592 reflectionsΔρmax = 1.67 e Å−3
227 parametersΔρmin = −1.39 e Å−3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (2)
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.
xyzUiso*/Ueq
Br10.19570 (14)0.16142 (4)0.64242 (3)0.07526 (19)
S10.3284 (3)0.41677 (8)0.33059 (7)0.0550 (4)
O10.2257 (8)0.6333 (2)−0.00717 (17)0.0636 (9)
O20.2253 (9)0.5689 (2)0.25867 (18)0.0687 (8)
N10.2711 (9)0.6635 (2)0.1388 (2)0.0551 (12)
H1A0.23520.70340.19310.066*
N30.5949 (10)0.2787 (3)0.1998 (2)0.0621 (13)
N40.5645 (10)0.2351 (2)0.2632 (2)0.0597 (8)
N20.4834 (9)0.4276 (2)0.1728 (2)0.0539 (8)
H2A0.57260.39920.12290.065*
C4−0.2078 (13)0.9136 (3)0.0368 (3)0.0711 (18)
H4B−0.31080.9254−0.01120.085*
C5−0.0907 (12)0.8176 (3)0.0241 (3)0.0610 (16)
H5A−0.12310.7628−0.03320.073*
C100.4756 (11)0.3703 (3)0.2263 (3)0.0512 (11)
C160.1797 (12)0.3039 (3)0.5556 (3)0.0632 (17)
H16A0.08380.34860.60610.076*
C150.2691 (13)0.2067 (3)0.5481 (3)0.0603 (10)
C120.3711 (10)0.2674 (3)0.4098 (2)0.0471 (9)
C140.4058 (11)0.1370 (3)0.4729 (3)0.0598 (11)
H14A0.45960.07010.46880.072*
C170.2354 (12)0.3345 (3)0.4857 (3)0.0587 (11)
H17A0.18070.40140.49000.070*
C80.4114 (12)0.5638 (3)0.1200 (3)0.0560 (15)
H8A0.64860.57230.11440.067*
H8B0.30680.51160.06270.067*
C90.3647 (11)0.5237 (3)0.1913 (2)0.0475 (10)
C110.4297 (11)0.2963 (3)0.3341 (2)0.0483 (10)
C130.4598 (12)0.1698 (3)0.4041 (3)0.0601 (16)
H13A0.55710.12530.35370.072*
C70.1970 (11)0.6938 (3)0.0722 (3)0.0521 (13)
C60.0730 (11)0.7991 (3)0.0926 (2)0.0489 (14)
C2−0.0154 (12)0.9776 (3)0.1919 (3)0.0601 (16)
H2B0.00741.03200.24940.072*
C3−0.1698 (12)0.9930 (3)0.1230 (3)0.0643 (17)
H3B−0.25331.05850.13320.077*
C10.1113 (12)0.8805 (3)0.1780 (3)0.0555 (15)
H1B0.22160.87010.22590.067*
U11U22U33U12U13U23
Br10.0941 (4)0.0888 (3)0.0604 (2)0.0226 (3)0.0361 (2)0.04206 (19)
S10.0804 (8)0.0441 (5)0.0406 (5)0.0193 (5)0.0286 (5)0.0118 (4)
O10.106 (2)0.0501 (14)0.0414 (6)0.0279 (14)0.0433 (10)0.0174 (7)
O20.1043 (12)0.0616 (16)0.0469 (7)0.0256 (13)0.0439 (6)0.0207 (9)
N10.082 (3)0.0452 (17)0.0435 (16)0.0255 (16)0.0332 (18)0.0165 (13)
N30.099 (3)0.0488 (17)0.0448 (17)0.0288 (18)0.0270 (19)0.0193 (13)
N40.1059 (15)0.0386 (15)0.0399 (8)0.0252 (12)0.0297 (7)0.0154 (8)
N20.075 (2)0.0474 (5)0.0474 (5)0.0157 (15)0.0353 (16)0.0212 (3)
C40.097 (4)0.049 (2)0.070 (3)0.025 (2)0.022 (3)0.022 (2)
C50.080 (3)0.042 (2)0.053 (2)0.012 (2)0.009 (2)0.0102 (18)
C100.073 (3)0.0390 (7)0.0442 (7)0.0091 (19)0.024 (2)0.0156 (4)
C160.080 (3)0.054 (2)0.051 (2)0.012 (2)0.034 (2)0.0102 (19)
C150.0825 (16)0.0564 (19)0.0442 (9)−0.0018 (12)0.0194 (8)0.0211 (8)
C120.0546 (15)0.0498 (18)0.0351 (9)0.0036 (12)0.0172 (7)0.0131 (8)
C140.066 (2)0.066 (2)0.0600 (12)0.0136 (14)0.0282 (10)0.0337 (10)
C170.078 (2)0.050 (2)0.0448 (11)0.0131 (15)0.0261 (10)0.0109 (10)
C80.064 (3)0.061 (2)0.053 (2)0.026 (2)0.035 (2)0.0269 (16)
C90.0644 (16)0.041 (2)0.0353 (8)0.0082 (16)0.0210 (7)0.0104 (12)
C110.0753 (18)0.0407 (18)0.0336 (10)0.0106 (14)0.0223 (9)0.0165 (9)
C130.094 (3)0.042 (2)0.046 (2)0.010 (2)0.030 (2)0.0159 (16)
C70.071 (3)0.047 (2)0.0344 (7)0.0104 (19)0.0185 (14)0.0105 (9)
C60.061 (3)0.047 (2)0.0339 (18)0.0118 (19)0.030 (2)0.0067 (16)
C20.078 (3)0.043 (2)0.050 (2)0.009 (2)0.019 (2)0.0062 (18)
C30.080 (3)0.052 (2)0.065 (3)0.031 (2)0.025 (3)0.0211 (19)
C10.071 (3)0.047 (2)0.046 (2)0.016 (2)0.023 (2)0.0120 (17)
Br1—C151.898 (5)C16—C171.382 (7)
S1—C101.714 (4)C16—H16A0.9300
S1—C111.741 (5)C15—C141.387 (6)
O1—C71.242 (4)C12—C131.370 (6)
O2—C91.214 (5)C12—C171.380 (5)
N1—C71.323 (6)C12—C111.461 (6)
N1—C81.430 (5)C14—C131.383 (7)
N1—H1A0.8600C14—H14A0.9300
N3—C101.285 (5)C17—H17A0.9300
N3—N41.387 (6)C8—C91.483 (7)
N4—C111.299 (5)C8—H8A0.9700
N2—C91.349 (5)C8—H8B0.9700
N2—C101.381 (6)C13—H13A0.9300
N2—H2A0.8600C7—C61.469 (6)
C4—C51.361 (7)C6—C11.383 (5)
C4—C31.382 (6)C2—C31.335 (7)
C4—H4B0.9300C2—C11.388 (6)
C5—C61.367 (7)C2—H2B0.9300
C5—H5A0.9300C3—H3B0.9300
C16—C151.359 (7)C1—H1B0.9300
C10—S1—C1186.0 (2)C16—C17—H17A119.5
C7—N1—C8119.6 (3)N1—C8—C9112.3 (3)
C7—N1—H1A120.2N1—C8—H8A109.1
C8—N1—H1A120.2C9—C8—H8A109.1
C10—N3—N4110.7 (4)N1—C8—H8B109.1
C11—N4—N3113.3 (3)C9—C8—H8B109.1
C9—N2—C10126.3 (3)H8A—C8—H8B107.9
C9—N2—H2A116.8O2—C9—N2121.9 (4)
C10—N2—H2A116.8O2—C9—C8125.0 (4)
C5—C4—C3118.3 (5)N2—C9—C8113.1 (3)
C5—C4—H4B120.9N4—C11—C12123.3 (4)
C3—C4—H4B120.9N4—C11—S1113.4 (3)
C4—C5—C6122.2 (4)C12—C11—S1123.3 (3)
C4—C5—H5A118.9C12—C13—C14120.4 (4)
C6—C5—H5A118.9C12—C13—H13A119.8
N3—C10—N2119.8 (4)C14—C13—H13A119.8
N3—C10—S1116.5 (4)O1—C7—N1120.5 (4)
N2—C10—S1123.6 (3)O1—C7—C6120.0 (4)
C15—C16—C17118.0 (4)N1—C7—C6119.4 (3)
C15—C16—H16A121.0C5—C6—C1118.3 (4)
C17—C16—H16A121.0C5—C6—C7118.5 (3)
C16—C15—C14122.6 (5)C1—C6—C7123.2 (4)
C16—C15—Br1119.4 (3)C3—C2—C1120.2 (4)
C14—C15—Br1118.0 (4)C3—C2—H2B119.9
C13—C12—C17119.7 (4)C1—C2—H2B119.9
C13—C12—C11117.6 (3)C2—C3—C4121.2 (4)
C17—C12—C11122.6 (4)C2—C3—H3B119.4
C13—C14—C15118.2 (4)C4—C3—H3B119.4
C13—C14—H14A120.9C6—C1—C2119.8 (4)
C15—C14—H14A120.9C6—C1—H1B120.1
C12—C17—C16121.0 (4)C2—C1—H1B120.1
C12—C17—H17A119.5
C10—N3—N4—C11−1.0 (5)C13—C12—C11—N4−0.9 (6)
C3—C4—C5—C6−2.5 (8)C17—C12—C11—N4178.3 (4)
N4—N3—C10—N2179.7 (4)C13—C12—C11—S1179.6 (3)
N4—N3—C10—S12.2 (5)C17—C12—C11—S1−1.2 (6)
C9—N2—C10—N3179.2 (4)C10—S1—C11—N41.5 (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—C141.8 (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—O15.2 (6)
C16—C15—C14—C131.7 (7)C8—N1—C7—C6−176.1 (4)
Br1—C15—C14—C13−179.9 (3)C4—C5—C6—C11.8 (7)
C13—C12—C17—C16−1.6 (6)C4—C5—C6—C7−178.7 (5)
C11—C12—C17—C16179.2 (4)O1—C7—C6—C517.2 (7)
C15—C16—C17—C121.4 (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—C118.0 (7)
C10—N2—C9—C8−180.0 (4)C1—C2—C3—C40.1 (8)
N1—C8—C9—O2−0.2 (6)C5—C4—C3—C21.6 (8)
N1—C8—C9—N2177.4 (3)C5—C6—C1—C20.0 (7)
N3—N4—C11—C12179.8 (4)C7—C6—C1—C2−179.5 (4)
N3—N4—C11—S1−0.6 (5)C3—C2—C1—C6−0.9 (8)
D—H···AD—HH···AD···AD—H···A
C16—H16A···O2i0.932.493.400 (5)168
N2—H2A···O1ii0.861.992.835 (5)167
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C16—H16A⋯O2i0.932.493.400 (5)168
N2—H2A⋯O1ii0.861.992.835 (5)167

Symmetry codes: (i) ; (ii) .

  6 in total

1.  Synthesis and in vitro antifungal activity of 2-aryl-5-phenylsulfonyl-1,3,4-thiadiazole derivatives.

Authors:  A Foroumadi; M Daneshtalab; A Shafiee
Journal:  Arzneimittelforschung       Date:  1999-12

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  (2R)-N-[5-(4-Chloro-phen-yl)-1,3,4-thia-diazol-2-yl]-2-(cinnamoylamino)propanamide.

Authors:  Shao-Hua Li; Hui-Ming Huang; Bin-Hai Kuang; Guo-Gang Tu; Cheng-Mei Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-24

4.  N-(2,4-Dichloro-phen-yl)benzamide.

Authors:  B Thimme Gowda; Miroslav Tokarčík; Jozef Kožíšek; B P Sowmya; Hartmut Fuess
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-03

5.  Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold.

Authors:  GuoGang Tu; ShaoHua Li; HuiMing Huang; Gang Li; Fang Xiong; Xi Mai; HuaWei Zhu; BinHai Kuang; Wen Fang Xu
Journal:  Bioorg Med Chem       Date:  2008-06-05       Impact factor: 3.641

6.  (2R)-2-Cinnamoylamino-N-[5-(4-methoxy-phen-yl)-1,3,4-thia-diazol-2-yl]propanamide.

Authors:  Shao-Hua Li; Gang Li; Hui-Ming Huang; Guo-Gang Tu; Cheng-Mei Liu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-06
  6 in total

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