Literature DB >> 24109407

1-(5-Bromo-2-oxoindolin-3-yl-idene)-4-phenyl-thio-semicarbazide.

Katlen C T Bandeira1, Leandro Bresolin, Christian Näther, Inke Jess, Adriano Bof de Oliveira.   

Abstract

In the title compound, C15H11BrN4OS, the least-squares plane through the 5-bromo-isatin fragment forms a dihedral angle of 13.63 (14)° with the phenyl ring. The mol-ecular conformation features intra-molecular N-H⋯N and N-H⋯O hydrogen bonds. In the crystal, mol-ecules are connected via pairs of N-H⋯O inter-actions into centrosymmetric dimers. Additionally, π-π stacking inter-actions link mol-ecules into chains parallel to the a axis with short C⋯C distances being observed between the phenyl and thio-carbonyl [3.236 (8) Å] groups and between the thio-carbonyl and carbonyl [3.351 (4) Å] groups of stacked mol-ecules.

Entities:  

Year:  2013        PMID： 24109407      PMCID： PMC3793820          DOI： 10.1107/S1600536813020497

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


Related literature

For the pharmacological properties of isatin-thio­semi­carbazone derivatives against cruzain, falcipain-2 and rhodesain, see: Chiyanzu et al. (2003 ▶). For the synthesis of 5-bromo­isatin-3-thio­semicarbazone, see: Campaigne & Archer (1952 ▶). For the crystal structure of 1-(5-bromo-2-oxoindolin-3-yl­idene)thio­semicarbazide aceto­nitrile monosolvate, see: Pederzolli et al. (2011 ▶).

Experimental

Crystal data

C15H11BrN4OS M = 375.25 Monoclinic, a = 5.6882 (3) Å b = 18.4086 (9) Å c = 14.4668 (10) Å β = 91.272 (8)° V = 1514.47 (15) Å3 Z = 4 Mo Kα radiation μ = 2.86 mm−1 T = 200 K 0.12 × 0.10 × 0.08 mm

Data collection

Stoe IPDS-1 diffractometer Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 ▶) T min = 0.633, T max = 0.677 13502 measured reflections 2903 independent reflections 2235 reflections with I > 2σ(I) R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.105 S = 1.04 2903 reflections 199 parameters H-atom parameters constrained Δρmax = 0.67 e Å−3 Δρmin = −1.11 e Å−3 Data collection: X-AREA (Stoe & Cie, 2008 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I, publication_text. DOI: 10.1107/S1600536813020497/fy2102sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020497/fy2102Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813020497/fy2102Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H11BrN4OSF(000) = 752
Mr = 375.25Dx = 1.646 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 13698 reflections
a = 5.6882 (3) Åθ = 2.6–26.0°
b = 18.4086 (9) ŵ = 2.86 mm−1
c = 14.4668 (10) ÅT = 200 K
β = 91.272 (8)°Block, yellow
V = 1514.47 (15) Å30.12 × 0.10 × 0.08 mm
Z = 4
Stoe IPDS-1 diffractometer2903 independent reflections
Radiation source: fine-focus sealed tube, Stoe IPDS-12235 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
φ scansθmax = 26.0°, θmin = 2.6°
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008)h = −6→6
Tmin = 0.633, Tmax = 0.677k = −22→22
13502 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0517P)2 + 1.4796P] where P = (Fo2 + 2Fc2)/3
2903 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.67 e Å−3
0 restraintsΔρmin = −1.11 e Å−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
N10.0836 (5)0.47322 (14)1.38606 (19)0.0312 (6)
H1−0.02710.45831.42310.037*
C10.2595 (5)0.51911 (16)1.4116 (2)0.0283 (7)
O10.2888 (4)0.54902 (12)1.48762 (15)0.0316 (5)
C20.4124 (5)0.52739 (15)1.3285 (2)0.0247 (6)
C30.3024 (5)0.48403 (15)1.2553 (2)0.0261 (6)
C40.3560 (6)0.47236 (17)1.1638 (2)0.0324 (7)
H40.49150.49341.13740.039*
C50.2042 (7)0.42873 (18)1.1120 (2)0.0374 (8)
Br10.28023 (10)0.40737 (3)0.98769 (3)0.0688 (2)
C60.0060 (6)0.39716 (18)1.1491 (3)0.0381 (8)
H6−0.09340.36751.11130.046*
C7−0.0482 (6)0.40850 (17)1.2412 (3)0.0351 (8)
H7−0.18260.38681.26750.042*
C80.1004 (5)0.45251 (16)1.2930 (2)0.0283 (7)
N20.6012 (4)0.56591 (13)1.32193 (18)0.0256 (5)
N30.6730 (5)0.60375 (13)1.39722 (17)0.0260 (5)
H30.60040.59761.44970.031*
C90.8582 (5)0.65192 (15)1.3933 (2)0.0245 (6)
S10.91317 (16)0.70212 (5)1.48665 (6)0.0369 (2)
N40.9676 (4)0.65094 (13)1.31167 (17)0.0260 (5)
H4A0.91230.61861.27210.031*
C101.1570 (5)0.69326 (15)1.2785 (2)0.0241 (6)
C111.3184 (5)0.72936 (16)1.3353 (2)0.0270 (6)
H111.30350.72831.40050.032*
C121.5030 (6)0.76727 (17)1.2954 (3)0.0348 (7)
H121.61350.79221.33400.042*
C131.5277 (6)0.76906 (19)1.2009 (3)0.0373 (8)
H131.65370.79521.17450.045*
C141.3681 (6)0.7327 (2)1.1451 (2)0.0410 (8)
H141.38470.73351.07990.049*
C151.1830 (6)0.6949 (2)1.1832 (2)0.0355 (8)
H151.07360.67001.14400.043*
U11U22U33U12U13U23
N10.0231 (15)0.0324 (14)0.0385 (15)−0.0034 (10)0.0124 (11)0.0030 (11)
C10.0216 (17)0.0269 (15)0.0367 (18)0.0058 (11)0.0065 (13)0.0074 (12)
O10.0272 (13)0.0369 (12)0.0312 (12)0.0018 (9)0.0096 (9)0.0014 (9)
C20.0189 (16)0.0248 (14)0.0307 (16)0.0013 (11)0.0065 (12)0.0032 (11)
C30.0218 (17)0.0222 (14)0.0344 (17)−0.0003 (11)0.0059 (12)0.0043 (12)
C40.0320 (19)0.0305 (16)0.0350 (18)−0.0055 (13)0.0058 (14)0.0036 (13)
C50.047 (2)0.0325 (17)0.0329 (18)−0.0087 (15)0.0038 (15)0.0041 (13)
Br10.1019 (4)0.0700 (3)0.0350 (2)−0.0476 (3)0.0120 (2)−0.00818 (19)
C60.036 (2)0.0311 (17)0.046 (2)−0.0080 (14)−0.0056 (15)0.0015 (14)
C70.0242 (18)0.0318 (16)0.050 (2)−0.0061 (13)0.0075 (14)0.0040 (14)
C80.0219 (17)0.0252 (14)0.0380 (18)0.0012 (11)0.0067 (13)0.0059 (12)
N20.0233 (14)0.0235 (12)0.0300 (14)0.0007 (10)0.0042 (10)0.0025 (10)
N30.0251 (14)0.0289 (13)0.0245 (13)−0.0019 (10)0.0072 (10)0.0029 (10)
C90.0223 (16)0.0254 (14)0.0259 (15)0.0028 (11)0.0025 (12)0.0038 (11)
S10.0411 (5)0.0419 (5)0.0279 (4)−0.0053 (4)0.0071 (3)−0.0087 (3)
N40.0242 (14)0.0281 (12)0.0260 (13)−0.0050 (10)0.0048 (10)−0.0026 (10)
C100.0208 (16)0.0257 (14)0.0258 (15)0.0011 (11)0.0024 (11)0.0032 (11)
C110.0240 (17)0.0273 (15)0.0297 (16)0.0001 (12)−0.0003 (12)−0.0007 (12)
C120.0236 (18)0.0298 (16)0.051 (2)−0.0014 (12)−0.0024 (14)0.0018 (14)
C130.0224 (18)0.0391 (18)0.051 (2)−0.0013 (13)0.0071 (15)0.0145 (15)
C140.031 (2)0.062 (2)0.0303 (18)−0.0024 (16)0.0070 (14)0.0084 (16)
C150.0253 (18)0.053 (2)0.0278 (17)−0.0086 (15)0.0007 (13)−0.0007 (14)
N1—C11.355 (4)N3—C91.379 (4)
N1—C81.405 (4)N3—H30.8800
N1—H10.8800C9—N41.347 (4)
C1—O11.238 (4)C9—S11.660 (3)
C1—C21.507 (4)N4—C101.421 (4)
C2—N21.292 (4)N4—H4A0.8800
C2—C31.456 (4)C10—C111.388 (4)
C3—C41.382 (5)C10—C151.391 (4)
C3—C81.408 (4)C11—C121.397 (5)
C4—C51.387 (5)C11—H110.9500
C4—H40.9500C12—C131.378 (5)
C5—C61.387 (5)C12—H120.9500
C5—Br11.899 (4)C13—C141.375 (5)
C6—C71.390 (5)C13—H130.9500
C6—H60.9500C14—C151.386 (5)
C7—C81.380 (5)C14—H140.9500
C7—H70.9500C15—H150.9500
N2—N31.349 (4)
C1—N1—C8111.4 (3)N2—N3—C9121.1 (2)
C1—N1—H1124.3N2—N3—H3119.4
C8—N1—H1124.3C9—N3—H3119.4
O1—C1—N1127.1 (3)N4—C9—N3113.3 (3)
O1—C1—C2126.5 (3)N4—C9—S1129.7 (2)
N1—C1—C2106.3 (3)N3—C9—S1117.0 (2)
N2—C2—C3126.3 (3)C9—N4—C10131.0 (3)
N2—C2—C1127.5 (3)C9—N4—H4A114.5
C3—C2—C1106.2 (3)C10—N4—H4A114.5
C4—C3—C8120.4 (3)C11—C10—C15119.5 (3)
C4—C3—C2133.0 (3)C11—C10—N4124.0 (3)
C8—C3—C2106.6 (3)C15—C10—N4116.4 (3)
C3—C4—C5117.4 (3)C10—C11—C12119.2 (3)
C3—C4—H4121.3C10—C11—H11120.4
C5—C4—H4121.3C12—C11—H11120.4
C6—C5—C4122.3 (3)C13—C12—C11121.1 (3)
C6—C5—Br1118.9 (3)C13—C12—H12119.5
C4—C5—Br1118.6 (3)C11—C12—H12119.5
C5—C6—C7120.5 (3)C14—C13—C12119.3 (3)
C5—C6—H6119.7C14—C13—H13120.3
C7—C6—H6119.7C12—C13—H13120.3
C8—C7—C6117.5 (3)C13—C14—C15120.6 (3)
C8—C7—H7121.2C13—C14—H14119.7
C6—C7—H7121.2C15—C14—H14119.7
C7—C8—N1128.8 (3)C14—C15—C10120.2 (3)
C7—C8—C3121.8 (3)C14—C15—H15119.9
N1—C8—C3109.4 (3)C10—C15—H15119.9
C2—N2—N3117.5 (3)
C8—N1—C1—O1177.1 (3)C4—C3—C8—C71.0 (5)
C8—N1—C1—C2−2.2 (3)C2—C3—C8—C7179.0 (3)
O1—C1—C2—N21.1 (5)C4—C3—C8—N1−179.2 (3)
N1—C1—C2—N2−179.6 (3)C2—C3—C8—N1−1.2 (3)
O1—C1—C2—C3−177.9 (3)C3—C2—N2—N3178.6 (3)
N1—C1—C2—C31.5 (3)C1—C2—N2—N3−0.2 (4)
N2—C2—C3—C4−1.5 (5)C2—N2—N3—C9−173.3 (3)
C1—C2—C3—C4177.5 (3)N2—N3—C9—N4−6.0 (4)
N2—C2—C3—C8−179.2 (3)N2—N3—C9—S1173.5 (2)
C1—C2—C3—C8−0.2 (3)N3—C9—N4—C10177.3 (3)
C8—C3—C4—C5−0.2 (5)S1—C9—N4—C10−2.2 (5)
C2—C3—C4—C5−177.6 (3)C9—N4—C10—C1121.9 (5)
C3—C4—C5—C6−0.3 (5)C9—N4—C10—C15−161.0 (3)
C3—C4—C5—Br1−176.8 (2)C15—C10—C11—C120.6 (4)
C4—C5—C6—C70.1 (6)N4—C10—C11—C12177.7 (3)
Br1—C5—C6—C7176.6 (3)C10—C11—C12—C13−0.3 (5)
C5—C6—C7—C80.6 (5)C11—C12—C13—C14−0.2 (5)
C6—C7—C8—N1179.0 (3)C12—C13—C14—C150.4 (5)
C6—C7—C8—C3−1.2 (5)C13—C14—C15—C10−0.1 (6)
C1—N1—C8—C7−178.0 (3)C11—C10—C15—C14−0.4 (5)
C1—N1—C8—C32.2 (3)N4—C10—C15—C14−177.7 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.002.858 (3)166
N3—H3···O10.882.072.762 (3)135
N4—H4A···N20.882.162.613 (4)112
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.882.002.858 (3)166
N3—H3⋯O10.882.072.762 (3)135
N4—H4A⋯N20.882.162.613 (4)112

Symmetry code: (i) .

  3 in total

1.  A short history of SHELX.

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

2.  Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain.

Authors:  Idan Chiyanzu; Elizabeth Hansell; Jiri Gut; Philip J Rosenthal; James H McKerrow; Kelly Chibale
Journal:  Bioorg Med Chem Lett       Date:  2003-10-20       Impact factor: 2.823

3.  1-(5-Bromo-2-oxoindolin-3-yl-idene)thio-semicarbazide acetonitrile monosolvate.

Authors:  Fernanda Rosi Soares Pederzolli; Leandro Bresolin; Vanessa Santana Carratu; Aline Locatelli; Adriano Bof de Oliveira
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-25
  3 in total

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