Literature DB >> 22091178

3-Amino-N'-(2-oxoindolin-3-yl-idene)benzohydrazide.

Rifat Ara Jamal, Uzma Ashiq, Sammer Yousuf, Qurrat Ul Ain.   

Abstract

The title compound, C(15)H(12)N(4)O(2), contains two substituted benzohydrazide and indole rings linked via a C=N double bond. The dihedral angle between the benzene ring and the indole ring system is 11.38 (10)°. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond, forming a six-membered ring. The crystal structure is consolidated by inter-molecular N-H⋯O and C-H⋯O inter-actions, which result in sheets.

Entities:  

Year:  2011        PMID： 22091178      PMCID： PMC3213601          DOI： 10.1107/S1600536811029242

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


Related literature

For the biological activity of related compounds, see: Ashiq et al. (2008 ▶); Maqsood et al. (2006 ▶); Sarangapani & Reddy (1994 ▶). For related structures, see: Bai et al. (2006 ▶); Yang & Pan (2004 ▶).

Experimental

Crystal data

C15H12N4O2 M = 280.29 Monoclinic, a = 8.8036 (8) Å b = 8.9040 (7) Å c = 17.0732 (14) Å β = 92.335 (2)° V = 1337.21 (19) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 273 K 0.17 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.984, T max = 0.989 7637 measured reflections 2491 independent reflections 1551 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.122 S = 0.99 2491 reflections 198 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.18 e Å−3 Δρmin = −0.17 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029242/pv2431sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029242/pv2431Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811029242/pv2431Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H12N4O2F(000) = 584
Mr = 280.29Dx = 1.392 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1161 reflections
a = 8.8036 (8) Åθ = 2.4–27.8°
b = 8.9040 (7) ŵ = 0.10 mm−1
c = 17.0732 (14) ÅT = 273 K
β = 92.335 (2)°Block, colorless
V = 1337.21 (19) Å30.17 × 0.17 × 0.12 mm
Z = 4
Bruker SMART APEX CCD area-detector diffractometer2491 independent reflections
Radiation source: fine-focus sealed tube1551 reflections with I > 2σ(I)
graphiteRint = 0.047
ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −10→10
Tmin = 0.984, Tmax = 0.989k = −10→10
7637 measured reflectionsl = −20→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.99w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3
2491 reflections(Δ/σ)max < 0.001
198 parametersΔρmax = 0.18 e Å−3
1 restraintΔρmin = −0.17 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
O10.66942 (18)0.35101 (18)−0.07613 (8)0.0531 (5)
O20.53184 (19)0.37905 (18)0.20442 (8)0.0568 (5)
N10.5172 (2)0.1671 (2)−0.13475 (10)0.0470 (5)
H1A0.55780.1631−0.17970.056*
N20.4730 (2)0.27880 (19)0.06115 (9)0.0407 (5)
N30.5848 (2)0.38136 (19)0.07676 (9)0.0415 (5)
H3A0.63770.41690.03980.050*
N40.8354 (3)0.8078 (3)0.32398 (15)0.0676 (7)
C10.2412 (3)0.0351 (3)−0.00233 (13)0.0488 (6)
H1B0.21750.05450.04930.059*
C20.1601 (3)−0.0703 (3)−0.04635 (15)0.0557 (7)
H2A0.0815−0.1229−0.02410.067*
C30.1950 (3)−0.0980 (3)−0.12350 (14)0.0569 (7)
H3B0.1379−0.1682−0.15240.068*
C40.3119 (3)−0.0245 (3)−0.15845 (13)0.0523 (7)
H4A0.3354−0.0442−0.21010.063*
C50.3923 (2)0.0790 (2)−0.11405 (12)0.0417 (6)
C60.5659 (3)0.2585 (3)−0.07583 (12)0.0409 (6)
C70.4654 (2)0.2238 (2)−0.00862 (11)0.0374 (5)
C80.3583 (2)0.1110 (2)−0.03664 (12)0.0391 (5)
C90.6110 (2)0.4264 (2)0.15255 (12)0.0406 (6)
C100.7362 (2)0.5353 (2)0.16743 (12)0.0400 (6)
C110.8540 (3)0.5576 (3)0.11661 (13)0.0518 (6)
H11A0.85820.50270.07040.062*
C120.9645 (3)0.6629 (3)0.13619 (15)0.0606 (7)
H12A1.04420.67780.10300.073*
C130.9587 (3)0.7457 (3)0.20365 (16)0.0586 (7)
H13A1.03420.81610.21540.070*
C140.8416 (3)0.7259 (3)0.25467 (14)0.0490 (6)
C150.7329 (3)0.6181 (2)0.23602 (13)0.0440 (6)
H15A0.65550.60090.27040.053*
H4C0.7478 (19)0.819 (3)0.3435 (17)0.099 (12)*
H4B0.889 (4)0.894 (3)0.3239 (17)0.101 (11)*
U11U22U33U12U13U23
O10.0485 (10)0.0635 (11)0.0480 (9)−0.0019 (9)0.0114 (8)0.0040 (8)
O20.0650 (11)0.0715 (12)0.0346 (8)−0.0188 (9)0.0111 (8)−0.0022 (8)
N10.0485 (12)0.0630 (12)0.0299 (9)0.0067 (11)0.0055 (9)0.0003 (9)
N20.0402 (11)0.0452 (11)0.0366 (10)0.0030 (9)0.0024 (9)0.0015 (8)
N30.0439 (11)0.0476 (11)0.0334 (10)−0.0005 (10)0.0080 (9)0.0016 (8)
N40.0598 (18)0.0655 (16)0.0765 (16)−0.0067 (14)−0.0089 (14)−0.0142 (14)
C10.0431 (14)0.0557 (15)0.0473 (13)0.0064 (13)0.0012 (12)0.0011 (12)
C20.0413 (15)0.0549 (16)0.0704 (17)0.0005 (13)−0.0028 (13)0.0059 (14)
C30.0515 (16)0.0529 (15)0.0644 (17)0.0076 (13)−0.0192 (14)−0.0053 (13)
C40.0566 (17)0.0566 (15)0.0429 (13)0.0126 (14)−0.0088 (13)−0.0042 (12)
C50.0392 (13)0.0476 (13)0.0377 (12)0.0125 (12)−0.0042 (11)0.0000 (11)
C60.0366 (14)0.0488 (14)0.0372 (12)0.0113 (12)0.0017 (11)0.0042 (11)
C70.0364 (13)0.0432 (13)0.0326 (11)0.0115 (11)0.0013 (10)0.0028 (10)
C80.0354 (12)0.0437 (13)0.0379 (11)0.0089 (11)−0.0004 (10)0.0025 (10)
C90.0436 (14)0.0440 (13)0.0345 (12)0.0075 (11)0.0040 (11)0.0023 (10)
C100.0361 (13)0.0412 (13)0.0426 (12)0.0055 (11)0.0021 (10)0.0070 (11)
C110.0452 (15)0.0603 (16)0.0504 (13)0.0042 (13)0.0079 (12)0.0053 (12)
C120.0403 (15)0.0737 (18)0.0685 (17)−0.0012 (14)0.0084 (14)0.0180 (15)
C130.0447 (16)0.0558 (16)0.0743 (17)−0.0074 (13)−0.0084 (14)0.0100 (14)
C140.0428 (15)0.0479 (14)0.0557 (14)0.0047 (12)−0.0055 (13)0.0030 (12)
C150.0377 (13)0.0472 (14)0.0470 (13)0.0014 (11)−0.0012 (11)0.0047 (11)
O1—C61.228 (2)C3—H3B0.9300
O2—C91.224 (2)C4—C51.372 (3)
N1—C61.351 (3)C4—H4A0.9300
N1—C51.407 (3)C5—C81.396 (3)
N1—H1A0.8600C6—C71.509 (3)
N2—C71.287 (2)C7—C81.446 (3)
N2—N31.361 (2)C9—C101.482 (3)
N3—C91.365 (2)C10—C151.385 (3)
N3—H3A0.8600C10—C111.393 (3)
N4—C141.393 (3)C11—C121.382 (3)
N4—H4C0.858 (10)C11—H11A0.9300
N4—H4B0.90 (3)C12—C131.370 (3)
C1—C21.382 (3)C12—H12A0.9300
C1—C81.383 (3)C13—C141.388 (3)
C1—H1B0.9300C13—H13A0.9300
C2—C31.387 (3)C14—C151.383 (3)
C2—H2A0.9300C15—H15A0.9300
C3—C41.376 (3)
C6—N1—C5112.13 (18)N2—C7—C8125.39 (19)
C6—N1—H1A123.9N2—C7—C6128.0 (2)
C5—N1—H1A123.9C8—C7—C6106.59 (17)
C7—N2—N3116.52 (17)C1—C8—C5119.6 (2)
N2—N3—C9118.39 (17)C1—C8—C7133.39 (19)
N2—N3—H3A120.8C5—C8—C7107.01 (18)
C9—N3—H3A120.8O2—C9—N3120.4 (2)
C14—N4—H4C117 (2)O2—C9—C10122.86 (19)
C14—N4—H4B113.9 (19)N3—C9—C10116.76 (18)
H4C—N4—H4B113 (3)C15—C10—C11119.5 (2)
C2—C1—C8118.6 (2)C15—C10—C9116.88 (19)
C2—C1—H1B120.7C11—C10—C9123.6 (2)
C8—C1—H1B120.7C12—C11—C10118.7 (2)
C1—C2—C3120.5 (2)C12—C11—H11A120.6
C1—C2—H2A119.7C10—C11—H11A120.6
C3—C2—H2A119.7C13—C12—C11121.2 (2)
C4—C3—C2121.7 (2)C13—C12—H12A119.4
C4—C3—H3B119.2C11—C12—H12A119.4
C2—C3—H3B119.2C12—C13—C14120.9 (2)
C5—C4—C3117.3 (2)C12—C13—H13A119.6
C5—C4—H4A121.4C14—C13—H13A119.6
C3—C4—H4A121.4C15—C14—C13117.9 (2)
C4—C5—C8122.3 (2)C15—C14—N4120.5 (2)
C4—C5—N1128.8 (2)C13—C14—N4121.5 (2)
C8—C5—N1108.91 (19)C14—C15—C10121.7 (2)
O1—C6—N1127.9 (2)C14—C15—H15A119.1
O1—C6—C7126.8 (2)C10—C15—H15A119.1
N1—C6—C7105.3 (2)
C7—N2—N3—C9−170.74 (18)N1—C5—C8—C70.4 (2)
C8—C1—C2—C3−0.5 (3)N2—C7—C8—C10.8 (4)
C1—C2—C3—C41.1 (4)C6—C7—C8—C1179.3 (2)
C2—C3—C4—C5−0.6 (3)N2—C7—C8—C5−177.82 (19)
C3—C4—C5—C8−0.4 (3)C6—C7—C8—C50.6 (2)
C3—C4—C5—N1178.9 (2)N2—N3—C9—O2−2.5 (3)
C6—N1—C5—C4179.2 (2)N2—N3—C9—C10178.53 (17)
C6—N1—C5—C8−1.4 (2)O2—C9—C10—C15−19.6 (3)
C5—N1—C6—O1−178.1 (2)N3—C9—C10—C15159.37 (19)
C5—N1—C6—C71.7 (2)O2—C9—C10—C11160.6 (2)
N3—N2—C7—C8178.30 (18)N3—C9—C10—C11−20.5 (3)
N3—N2—C7—C60.2 (3)C15—C10—C11—C12−0.2 (3)
O1—C6—C7—N2−3.2 (4)C9—C10—C11—C12179.6 (2)
N1—C6—C7—N2177.0 (2)C10—C11—C12—C13−0.7 (4)
O1—C6—C7—C8178.4 (2)C11—C12—C13—C140.2 (4)
N1—C6—C7—C8−1.4 (2)C12—C13—C14—C151.2 (4)
C2—C1—C8—C5−0.5 (3)C12—C13—C14—N4179.1 (2)
C2—C1—C8—C7−179.0 (2)C13—C14—C15—C10−2.2 (3)
C4—C5—C8—C11.0 (3)N4—C14—C15—C10179.9 (2)
N1—C5—C8—C1−178.47 (19)C11—C10—C15—C141.7 (3)
C4—C5—C8—C7179.85 (19)C9—C10—C15—C14−178.15 (19)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.022.785 (2)148
N3—H3A···O10.862.092.757 (2)133
N4—H4C···N2ii0.86 (2)2.61 (2)3.423 (3)158 (2)
C12—H12A···O1iii0.932.593.424 (3)149
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O2i0.862.022.785 (2)148
N3—H3A⋯O10.862.092.757 (2)133
N4—H4C⋯N2ii0.86 (2)2.61 (2)3.423 (3)158 (2)
C12—H12A⋯O1iii0.932.593.424 (3)149

Symmetry codes: (i) ; (ii) ; (iii) .

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