Literature DB >> 21587860

4-(3-Iodo-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide.

Humayun Pervez, Muhammad Yaqub, Muhammad Ramzan, M Nawaz Tahir.   

Abstract

In the title compound, C(15)H(11)IN(4)OS, intra-molecular N-H⋯N, N-H⋯O and C-H⋯S inter-actions generate one S(5) and two S(6) ring motifs. In the crystal, mol-ecules form centrosymmetric dimers via pairs of N-H⋯O inter-actions, generating R(2) (2)(8) ring motifs. In addition a short inter-molecular I⋯S contact of 3.352 (3) Å is observed.

Entities:  

Year:  2010        PMID： 21587860      PMCID： PMC3006823          DOI： 10.1107/S1600536810021938

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


Related literature

For the preparation of biologically important N 4-aryl-substituted isatin-3-thio­semicarbazones, see: Pervez et al. (2007 ▶, 2008 ▶, 2010a ▶). For a related structure, see: Pervez et al. (2010b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H11IN4OS M = 422.24 Monoclinic, a = 5.7620 (3) Å b = 16.7989 (11) Å c = 16.152 (1) Å β = 100.153 (4)° V = 1538.96 (16) Å3 Z = 4 Mo Kα radiation μ = 2.22 mm−1 T = 296 K 0.32 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.742, T max = 0.752 11310 measured reflections 2778 independent reflections 1677 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.055 wR(F 2) = 0.157 S = 1.01 2778 reflections 199 parameters H-atom parameters constrained Δρmax = 2.76 e Å−3 Δρmin = −0.48 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021938/gk2281sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021938/gk2281Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H11IN4OSF(000) = 824
Mr = 422.24Dx = 1.822 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1677 reflections
a = 5.7620 (3) Åθ = 2.7–25.3°
b = 16.7989 (11) ŵ = 2.22 mm−1
c = 16.152 (1) ÅT = 296 K
β = 100.153 (4)°Needle, yellow
V = 1538.96 (16) Å30.32 × 0.14 × 0.12 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer2778 independent reflections
Radiation source: fine-focus sealed tube1677 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 2.7°
ω scansh = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −20→20
Tmin = 0.742, Tmax = 0.752l = −16→19
11310 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0776P)2 + 1.1429P] where P = (Fo2 + 2Fc2)/3
2778 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 2.76 e Å−3
0 restraintsΔρmin = −0.47 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
I11.07185 (10)0.31162 (4)0.23986 (4)0.0483 (3)
S10.4332 (4)0.20616 (18)0.59942 (16)0.0586 (10)
O1−0.2092 (9)0.0552 (4)0.5161 (4)0.045 (2)
N1−0.4370 (12)0.0106 (4)0.3922 (4)0.040 (3)
N20.0812 (11)0.1226 (4)0.3935 (4)0.034 (2)
N30.1620 (11)0.1406 (4)0.4736 (4)0.037 (3)
N40.4525 (10)0.2139 (4)0.4329 (4)0.034 (2)
C1−0.2557 (14)0.0481 (5)0.4378 (6)0.039 (3)
C2−0.4343 (14)0.0140 (5)0.3070 (6)0.038 (3)
C3−0.5883 (15)−0.0147 (6)0.2406 (6)0.050 (3)
C4−0.5463 (17)−0.0022 (6)0.1609 (7)0.058 (4)
C5−0.3504 (17)0.0387 (6)0.1472 (6)0.055 (4)
C6−0.1928 (16)0.0702 (6)0.2141 (6)0.049 (3)
C7−0.2329 (13)0.0575 (5)0.2942 (5)0.035 (3)
C8−0.1107 (13)0.0803 (5)0.3755 (5)0.036 (3)
C90.3534 (13)0.1884 (5)0.4975 (5)0.036 (3)
C100.6498 (14)0.2638 (5)0.4318 (5)0.035 (3)
C110.7303 (13)0.2695 (5)0.3565 (6)0.038 (3)
C120.9304 (14)0.3131 (5)0.3511 (5)0.038 (3)
C131.0440 (15)0.3535 (5)0.4199 (6)0.044 (3)
C140.9691 (16)0.3505 (6)0.4947 (6)0.050 (3)
C150.7723 (16)0.3050 (6)0.5021 (6)0.048 (3)
H1−0.54474−0.013240.413440.0478*
H3−0.72140−0.042690.249130.0602*
H3A0.090850.121470.511760.0443*
H4−0.65213−0.021710.115250.0694*
H4A0.384840.197190.384280.0404*
H5−0.323070.045390.092580.0658*
H6−0.062630.099340.204730.0588*
H110.649380.243870.308990.0460*
H131.176080.383840.415140.0529*
H141.048530.378620.540720.0598*
H150.721300.301790.553510.0580*
U11U22U33U12U13U23
I10.0373 (4)0.0617 (5)0.0487 (4)0.0009 (3)0.0153 (3)0.0093 (3)
S10.0525 (15)0.083 (2)0.0409 (14)−0.0148 (14)0.0096 (11)0.0018 (14)
O10.038 (3)0.052 (4)0.050 (4)−0.003 (3)0.021 (3)−0.001 (3)
N10.034 (4)0.039 (4)0.052 (5)−0.007 (3)0.020 (3)0.000 (4)
N20.026 (4)0.041 (4)0.038 (4)−0.002 (3)0.011 (3)0.002 (3)
N30.032 (4)0.048 (5)0.034 (4)−0.006 (3)0.012 (3)0.005 (4)
N40.026 (4)0.037 (4)0.040 (4)−0.005 (3)0.009 (3)0.001 (3)
C10.030 (5)0.033 (5)0.058 (7)0.004 (4)0.023 (4)0.005 (5)
C20.027 (4)0.036 (5)0.054 (6)−0.002 (4)0.013 (4)0.008 (5)
C30.039 (5)0.048 (6)0.063 (7)−0.014 (4)0.010 (5)0.002 (5)
C40.051 (6)0.063 (7)0.058 (7)−0.013 (5)0.006 (5)−0.001 (6)
C50.063 (6)0.063 (7)0.039 (6)−0.016 (5)0.011 (5)0.001 (5)
C60.049 (5)0.049 (6)0.051 (6)−0.015 (5)0.016 (5)0.000 (5)
C70.036 (4)0.032 (5)0.040 (5)−0.005 (4)0.016 (4)0.002 (4)
C80.027 (4)0.044 (6)0.039 (5)0.006 (4)0.010 (4)0.007 (4)
C90.026 (4)0.037 (5)0.045 (5)0.001 (4)0.007 (4)0.006 (4)
C100.035 (5)0.036 (5)0.036 (5)0.005 (4)0.010 (4)0.003 (4)
C110.027 (4)0.036 (5)0.051 (6)0.005 (4)0.004 (4)0.005 (5)
C120.029 (4)0.035 (5)0.049 (6)0.009 (4)0.008 (4)0.010 (5)
C130.032 (5)0.039 (6)0.061 (7)−0.004 (4)0.005 (4)0.003 (5)
C140.047 (6)0.048 (6)0.057 (6)−0.012 (5)0.014 (5)−0.012 (5)
C150.040 (5)0.055 (6)0.052 (6)−0.008 (5)0.014 (4)−0.005 (5)
I1—C122.100 (8)C5—C61.388 (14)
S1—C91.656 (8)C6—C71.371 (12)
O1—C11.251 (11)C7—C81.429 (11)
N1—C11.326 (11)C10—C151.409 (13)
N1—C21.380 (11)C10—C111.379 (12)
N2—N31.330 (9)C11—C121.382 (11)
N2—C81.303 (10)C12—C131.367 (12)
N3—C91.364 (10)C13—C141.354 (13)
N4—C91.345 (10)C14—C151.390 (14)
N4—C101.415 (10)C3—H30.9300
N1—H10.8600C4—H40.9300
N3—H3A0.8600C5—H50.9300
N4—H4A0.8600C6—H60.9300
C1—C81.517 (12)C11—H110.9300
C2—C31.355 (13)C13—H130.9300
C2—C71.417 (11)C14—H140.9300
C3—C41.367 (14)C15—H150.9300
C4—C51.372 (14)
I1···S1i3.352 (3)C9···O1iv3.344 (10)
I1···S1ii3.979 (3)C10···C8iv3.560 (12)
I1···H3iii3.2000C11···C8iv3.307 (12)
I1···H4Aiv3.3000C11···N2iv3.180 (11)
S1···C153.183 (10)C12···N2iv3.355 (11)
S1···I1v3.352 (3)C13···N4iv3.303 (11)
S1···I1vi3.979 (3)C13···C9iv3.414 (12)
S1···H152.5100C14···C9iv3.505 (13)
O1···N23.028 (9)C15···S13.183 (10)
O1···N32.761 (9)C1···H3A2.4700
O1···C9vii3.344 (10)C1···H1ix2.9000
O1···C1viii3.168 (10)C1···H3Aviii3.0700
O1···O1viii3.157 (8)C5···H13x3.0200
O1···N1ix2.939 (9)C9···H152.8700
O1···C8viii3.241 (10)C12···H3iii3.0400
O1···H3A2.0700C13···H4iii3.0600
O1···H1ix2.0900C14···H5xi3.0500
N1···O1ix2.939 (9)C15···H5xi3.0100
N2···O13.028 (9)H1···O1ix2.0900
N2···N42.618 (9)H1···C1ix2.9000
N2···C11vii3.180 (11)H3···I1xii3.2000
N2···C12vii3.355 (11)H3···C12xii3.0400
N3···O12.761 (9)H3A···O12.0700
N4···C1iv3.247 (11)H3A···C12.4700
N4···N22.618 (9)H3A···C1viii3.0700
N4···C13vii3.303 (11)H4···C13xii3.0600
N2···H4A2.1800H4A···I1vii3.3000
C1···N4vii3.247 (11)H4A···N22.1800
C1···C9vii3.511 (12)H4A···H112.2500
C1···O1viii3.168 (10)H5···C14xiii3.0500
C8···O1viii3.241 (10)H5···C15xiii3.0100
C8···C10vii3.560 (12)H11···H4A2.2500
C8···C11vii3.307 (12)H13···C5xiv3.0200
C9···C14vii3.505 (13)H15···S12.5100
C9···C1iv3.511 (12)H15···C92.8700
C9···C13vii3.414 (12)
C1—N1—C2112.8 (7)S1—C9—N4129.2 (6)
N3—N2—C8118.6 (7)C11—C10—C15118.6 (8)
N2—N3—C9122.4 (6)N4—C10—C15124.8 (7)
C9—N4—C10130.6 (7)N4—C10—C11116.6 (7)
C2—N1—H1124.00C10—C11—C12120.4 (8)
C1—N1—H1124.00I1—C12—C13119.9 (6)
N2—N3—H3A119.00I1—C12—C11120.1 (6)
C9—N3—H3A119.00C11—C12—C13119.8 (8)
C10—N4—H4A115.00C12—C13—C14121.7 (8)
C9—N4—H4A115.00C13—C14—C15119.4 (9)
O1—C1—N1127.9 (8)C10—C15—C14120.1 (8)
N1—C1—C8105.9 (7)C2—C3—H3120.00
O1—C1—C8126.3 (7)C4—C3—H3120.00
C3—C2—C7120.5 (8)C3—C4—H4119.00
N1—C2—C3130.8 (8)C5—C4—H4119.00
N1—C2—C7108.7 (7)C4—C5—H5120.00
C2—C3—C4119.4 (9)C6—C5—H5120.00
C3—C4—C5121.1 (10)C5—C6—H6121.00
C4—C5—C6120.6 (9)C7—C6—H6121.00
C5—C6—C7118.7 (9)C10—C11—H11120.00
C6—C7—C8133.5 (8)C12—C11—H11120.00
C2—C7—C6119.8 (8)C12—C13—H13119.00
C2—C7—C8106.7 (7)C14—C13—H13119.00
N2—C8—C1126.3 (7)C13—C14—H14120.00
C1—C8—C7105.9 (7)C15—C14—H14120.00
N2—C8—C7127.8 (7)C10—C15—H15120.00
S1—C9—N3117.2 (6)C14—C15—H15120.00
N3—C9—N4113.6 (7)
C1—N1—C2—C3−178.2 (9)C3—C2—C7—C6−0.4 (13)
C2—N1—C1—O1−179.7 (8)C3—C2—C7—C8179.0 (8)
C2—N1—C1—C8−0.6 (9)C2—C3—C4—C50.2 (15)
C1—N1—C2—C70.2 (10)C3—C4—C5—C6−1.7 (16)
N3—N2—C8—C7176.9 (8)C4—C5—C6—C72.0 (15)
C8—N2—N3—C9−176.1 (7)C5—C6—C7—C8179.8 (9)
N3—N2—C8—C1−0.3 (12)C5—C6—C7—C2−1.0 (13)
N2—N3—C9—S1179.6 (6)C2—C7—C8—N2−178.4 (8)
N2—N3—C9—N4−1.0 (11)C6—C7—C8—N20.9 (16)
C10—N4—C9—S1−1.0 (13)C6—C7—C8—C1178.6 (10)
C9—N4—C10—C15−7.2 (14)C2—C7—C8—C1−0.7 (9)
C10—N4—C9—N3179.7 (7)N4—C10—C11—C12−176.1 (7)
C9—N4—C10—C11170.5 (8)C15—C10—C11—C121.6 (13)
O1—C1—C8—N2−2.3 (14)N4—C10—C15—C14177.9 (8)
O1—C1—C8—C7180.0 (8)C11—C10—C15—C140.3 (14)
N1—C1—C8—N2178.5 (8)C10—C11—C12—I1173.5 (6)
N1—C1—C8—C70.8 (9)C10—C11—C12—C13−2.7 (13)
N1—C2—C3—C4179.0 (9)I1—C12—C13—C14−174.5 (7)
C7—C2—C3—C40.8 (14)C11—C12—C13—C141.7 (13)
N1—C2—C7—C6−179.0 (8)C12—C13—C14—C150.3 (14)
N1—C2—C7—C80.4 (9)C13—C14—C15—C10−1.3 (14)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ix0.862.092.939 (9)169
N3—H3A···O10.862.072.761 (9)137
N4—H4A···N20.862.182.618 (9)111
C15—H15···S10.932.513.183 (10)129
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O1i0.862.092.939 (9)169
N3—H3A⋯O10.862.072.761 (9)137
N4—H4A⋯N20.862.182.618 (9)111
C15—H15⋯S10.932.513.183 (10)129

Symmetry code: (i) .

  5 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 of some N4-substituted isatin-3-thiosemicarbazones.

Authors:  H Pervez; M S Iqbal; M Y Tahir; M I Choudhary; K M Khan
Journal:  Nat Prod Res       Date:  2007-11       Impact factor: 2.861

3.  In vitro cytotoxic, antibacterial, antifungal and urease inhibitory activities of some N4- substituted isatin-3-thiosemicarbazones.

Authors:  Humayun Pervez; Mohammad S Iqbal; Muhammad Younas Tahir; Faiz-ul-Hassan Nasim; Muhammad Iqbal Choudhary; Khalid Mohammed Khan
Journal:  J Enzyme Inhib Med Chem       Date:  2008-12       Impact factor: 5.051

4.  4-(3-Methoxy-phen-yl)-1-(2-oxoindolin-3-yl-idene)thio-semicarbazide.

Authors:  Humayun Pervez; Mohammad S Iqbal; Naveeda Saira; Muhammad Yaqub; M Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-22

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein.

Authors:  Matthew D Hall; Kyle R Brimacombe; Matthew S Varonka; Kristen M Pluchino; Julie K Monda; Jiayang Li; Martin J Walsh; Matthew B Boxer; Timothy H Warren; Henry M Fales; Michael M Gottesman
Journal:  J Med Chem       Date:  2011-08-01       Impact factor: 7.446
  1 in total

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