Literature DB >> 25484825

Crystal structure of N-[(E)-(1,3-benzodioxol-5-yl)-methyl-idene]-4-chloro-aniline.

J Pablo García-Merinos1, Yliana López1, J Betzabe González-Campos1, Judit A Aviña-Verduzco1, Rosa E Del Río1, Rosa Santillan2.   

Abstract

In the title compound, C14H10ClNO2, obtained by the condensation of 4-chloro-aniline and piperonal, the five-membered ring is almost planar (r.m.s. deviation = 0.023 Å) and the dihedral angle between the aromatic rings is 43.22 (14)°. In the crystal, a short O⋯Cl contact of 3.173 (2) Å is observed. The mol-ecules are arranged into corrugated (010) layers.

Entities:  

Keywords:  O⋯Cl contact; Schiff base; crystal structure

Year:  2014        PMID： 25484825      PMCID： PMC4257285          DOI： 10.1107/S1600536814022892

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


Related literature

Schiff bases have applications in fields, such as organic synthesis (Meyer et al., 2007 ▶), catalysis (Itsuno et al., 1990 ▶), materials science (Sliwa et al., 2008 ▶), supra­molecular (Sreenivasulu et al., 2012 ▶) and coordination chemistry (Drozdzak et al., 2005 ▶; MacLachlan et al., 1996 ▶). They display a broad spectrum of biological (Garavelli et al., 1997 ▶; Ren et al., 2002 ▶) and pharmacological properties, such as anti­bacterial, analgesic, anti­pyretic, anti-inflammatory and anti­cancer activities and can act as plant-growth regulators (Prakash et al., 2011 ▶ and Gaur 2003 ▶). For related structures, see: Tahir et al. (2010a ▶,b ▶). For further synthetic details, see: Rodríguez et al. (2007 ▶); Domínguez et al. (2011 ▶).

Experimental

Crystal data

C14H10ClNO2 M = 259.69 Orthorhombic, a = 6.0014 (4) Å b = 13.9015 (16) Å c = 28.867 (3) Å V = 2408.3 (4) Å3 Z = 8 Mo Kα radiation μ = 0.31 mm−1 T = 293 K 0.19 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer 5318 measured reflections 2377 independent reflections 882 reflections with I > 2σ(I) R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.121 S = 0.88 2377 reflections 203 parameters All H-atom parameters refined Δρmax = 0.14 e Å−3 Δρmin = −0.14 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: HKL DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; 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, 2012 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814022892/hb7302sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022892/hb7302Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814022892/hb7302Isup3.cml Click here for additional data file. I . DOI: 10.1107/S1600536814022892/hb7302fig1.tif View of (I), with displacement ellipsoids drawn at 30% probability level. CCDC reference: 1029773 Additional supporting information: crystallographic information; 3D view; checkCIF report
C14H10ClNO2Dx = 1.432 Mg m−3
Mr = 259.69Melting point: 347(2) K
Orthorhombic, PcabMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2acCell parameters from 600 reflections
a = 6.0014 (4) Åθ = 2.9–27.7°
b = 13.9015 (16) ŵ = 0.31 mm−1
c = 28.867 (3) ÅT = 293 K
V = 2408.3 (4) Å3Block, colourless
Z = 80.19 × 0.10 × 0.08 mm
F(000) = 1072
Nonius KappaCCD diffractometer882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.079
Graphite monochromatorθmax = 27.7°, θmin = 2.9°
φ and ω scansh = −7→5
5318 measured reflectionsk = −18→8
2377 independent reflectionsl = −33→37
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121All H-atom parameters refined
S = 0.88w = 1/[σ2(Fo2) + (0.0356P)2] where P = (Fo2 + 2Fc2)/3
2377 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.14 e Å−3
Experimental. Spectroscopic data for the title compound: IR(ATR) νmax cm-1: 2894 (CH2), 1600 (C=N), 1270 (C-O-C), 1490 (C=C), 827 (aromatic C-H), 789 (C-Cl) ; MS, (DIP 70 eV) for C14H10ClNO2m/z: (%): 259([M+],100), 261 ([M+2], 32), 138 (19), 121 (21), 75 (86). 1H NMR (400 MHz, CDCl3) δ: 8.30 (s, 1H, H-7), 7.51 (d, J= 1.6 Hz, 1H, H-9), 7.34 (d, J= 8.8 Hz, 2H,H-5,3), 7.26 (dd, J= 8.0, 1.6 Hz, 1H, H-13), 7.12 (d, J= 8.8 Hz, 2H, H-6,2), 6.88 (d, J= 8.0 Hz, 1H, H-12), 6.04 (s, 2H, H-14).13C NMR (100 MHz, CDCl3)δ: 159.70 (C-7), 150.69 (C-10), 150.44 (C-11), 148.45 (C-8), 131.12 (C-4), 130.87 (C-1), 129.16 (C-5,3), 125.93 (C-13), 122.17 (C-6,2), 108.22 (C-12), 106.77 (C-9), 101.65 (C-14).
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl11.12362 (17)0.14475 (7)0.07300 (4)0.0934 (5)
O10.5831 (4)0.12741 (17)0.47355 (10)0.0907 (12)
O20.9308 (4)0.07606 (17)0.45147 (10)0.0896 (11)
N10.9505 (4)0.10652 (15)0.27165 (11)0.0565 (10)
C10.9840 (5)0.11197 (19)0.22375 (14)0.0501 (14)
C20.8314 (6)0.0822 (2)0.19112 (17)0.0583 (14)
C30.8719 (6)0.0919 (2)0.14533 (17)0.0630 (14)
C41.0729 (6)0.13107 (19)0.13112 (13)0.0593 (14)
C51.2271 (6)0.1580 (2)0.16245 (17)0.0643 (16)
C61.1841 (5)0.1488 (2)0.20827 (18)0.0593 (14)
C70.7604 (6)0.1239 (2)0.28814 (15)0.0550 (14)
C80.7055 (5)0.12225 (18)0.33637 (13)0.0477 (14)
C90.8629 (6)0.0938 (2)0.36895 (15)0.0570 (14)
C100.8071 (6)0.0976 (2)0.41295 (16)0.0623 (14)
C110.5986 (6)0.1287 (2)0.42683 (15)0.0617 (14)
C120.4405 (6)0.1554 (2)0.39631 (15)0.0613 (14)
C130.4983 (5)0.1521 (2)0.35034 (15)0.0560 (14)
C140.7954 (9)0.0974 (6)0.4903 (2)0.110 (3)
H20.697 (5)0.0546 (18)0.1998 (10)0.066 (10)*
H30.772 (5)0.073 (2)0.1208 (12)0.082 (11)*
H51.351 (4)0.1855 (16)0.1520 (10)0.046 (8)*
H61.279 (5)0.1725 (16)0.2307 (11)0.059 (10)*
H70.649 (4)0.1402 (15)0.2697 (10)0.037 (8)*
H90.994 (4)0.0776 (16)0.3586 (10)0.042 (8)*
H120.296 (5)0.180 (2)0.4049 (11)0.079 (10)*
H130.389 (5)0.1706 (17)0.3261 (11)0.065 (9)*
H140.851 (10)0.150 (3)0.507 (2)0.20 (3)*
H14A0.770 (6)0.042 (2)0.5050 (16)0.115 (19)*
U11U22U33U12U13U23
Cl10.1101 (8)0.1037 (8)0.0663 (8)−0.0003 (6)0.0110 (7)0.0115 (6)
O10.075 (2)0.132 (2)0.065 (2)0.0176 (14)0.0076 (17)0.0032 (16)
O20.0707 (17)0.147 (2)0.051 (2)0.0218 (14)−0.0070 (17)0.0085 (16)
N10.0407 (17)0.0619 (16)0.067 (2)0.0055 (11)0.0016 (15)−0.0008 (14)
C10.046 (2)0.0462 (19)0.058 (3)0.0047 (14)0.004 (2)−0.0004 (16)
C20.051 (2)0.056 (2)0.068 (3)−0.0105 (16)−0.004 (2)−0.003 (2)
C30.063 (2)0.066 (2)0.060 (3)−0.0056 (18)−0.010 (2)−0.007 (2)
C40.068 (2)0.053 (2)0.057 (3)0.0078 (17)0.001 (2)0.0004 (17)
C50.050 (2)0.065 (2)0.078 (4)−0.0065 (17)0.007 (2)0.006 (2)
C60.043 (2)0.068 (2)0.067 (3)0.0002 (17)−0.007 (2)−0.006 (2)
C70.046 (2)0.052 (2)0.067 (3)0.0027 (15)−0.016 (2)0.0053 (18)
C80.043 (2)0.0461 (19)0.054 (3)0.0013 (14)−0.0044 (18)0.0058 (16)
C90.040 (2)0.064 (2)0.067 (3)0.0043 (16)0.009 (2)0.0027 (19)
C100.055 (2)0.069 (2)0.063 (3)0.0027 (16)−0.001 (2)0.005 (2)
C110.059 (2)0.071 (2)0.055 (3)−0.0004 (17)0.007 (2)0.001 (2)
C120.046 (2)0.066 (2)0.072 (3)0.0088 (18)0.003 (2)−0.004 (2)
C130.044 (2)0.060 (2)0.064 (3)0.0032 (15)−0.005 (2)0.0007 (19)
C140.098 (4)0.169 (7)0.062 (4)0.034 (4)0.003 (3)0.012 (4)
Cl1—C41.716 (4)C8—C131.372 (4)
O1—C111.352 (5)C9—C101.315 (6)
O1—C141.425 (6)C10—C111.383 (5)
O2—C101.370 (5)C11—C121.347 (5)
O2—C141.416 (6)C12—C131.372 (6)
N1—C11.399 (5)C2—H20.93 (3)
N1—C71.260 (4)C3—H30.96 (3)
C1—C21.377 (5)C5—H50.89 (2)
C1—C61.380 (4)C6—H60.92 (3)
C2—C31.351 (7)C7—H70.88 (3)
C3—C41.386 (5)C9—H90.87 (2)
C4—C51.347 (6)C12—H120.97 (3)
C5—C61.354 (7)C13—H130.99 (3)
C7—C81.431 (6)C14—H140.94 (5)
C8—C91.390 (5)C14—H14A0.89 (3)
C11—O1—C14106.3 (3)C11—C12—C13116.4 (3)
C10—O2—C14106.6 (3)C8—C13—C12121.6 (3)
C1—N1—C7119.6 (3)O1—C14—O2107.8 (4)
N1—C1—C2124.3 (3)C1—C2—H2121.2 (18)
N1—C1—C6117.7 (3)C3—C2—H2117.5 (18)
C2—C1—C6118.0 (4)C2—C3—H3125 (2)
C1—C2—C3121.3 (3)C4—C3—H3116 (2)
C2—C3—C4119.1 (4)C4—C5—H5117.8 (19)
Cl1—C4—C3119.2 (3)C6—C5—H5122.1 (19)
Cl1—C4—C5120.3 (3)C1—C6—H6116.3 (19)
C3—C4—C5120.6 (4)C5—C6—H6122.3 (19)
C4—C5—C6119.9 (3)N1—C7—H7120.4 (18)
C1—C6—C5121.2 (4)C8—C7—H7114.6 (18)
N1—C7—C8125.0 (3)C8—C9—H9117.1 (19)
C7—C8—C9120.4 (3)C10—C9—H9124.9 (19)
C7—C8—C13119.3 (3)C11—C12—H12124.3 (19)
C9—C8—C13120.2 (4)C13—C12—H12119.2 (19)
C8—C9—C10118.0 (3)C8—C13—H13118.0 (18)
O2—C10—C9129.6 (3)C12—C13—H13120.4 (18)
O2—C10—C11108.9 (4)O1—C14—H14105 (3)
C9—C10—C11121.5 (4)O1—C14—H14A105 (2)
O1—C11—C10110.3 (3)O2—C14—H14112 (4)
O1—C11—C12127.4 (3)O2—C14—H14A107 (3)
C10—C11—C12122.3 (4)H14—C14—H14A119 (4)
C14—O1—C11—C12−177.8 (4)C3—C4—C5—C6−1.5 (4)
C11—O1—C14—O2−3.3 (6)C4—C5—C6—C10.1 (4)
C14—O1—C11—C102.2 (5)N1—C7—C8—C9−4.5 (4)
C14—O2—C10—C11−1.7 (4)N1—C7—C8—C13173.3 (3)
C14—O2—C10—C9176.9 (4)C13—C8—C9—C10−0.7 (4)
C10—O2—C14—O13.1 (6)C9—C8—C13—C120.4 (4)
C7—N1—C1—C6142.4 (3)C7—C8—C9—C10177.1 (3)
C7—N1—C1—C2−38.2 (4)C7—C8—C13—C12−177.5 (3)
C1—N1—C7—C8−179.0 (3)C8—C9—C10—O2−178.4 (3)
C2—C1—C6—C51.8 (4)C8—C9—C10—C110.1 (4)
N1—C1—C6—C5−178.8 (3)O2—C10—C11—O1−0.4 (3)
N1—C1—C2—C3178.2 (3)O2—C10—C11—C12179.7 (3)
C6—C1—C2—C3−2.5 (4)C9—C10—C11—O1−179.1 (3)
C1—C2—C3—C41.2 (4)C9—C10—C11—C121.0 (5)
C2—C3—C4—Cl1−179.3 (2)O1—C11—C12—C13178.8 (3)
C2—C3—C4—C50.8 (4)C10—C11—C12—C13−1.3 (4)
Cl1—C4—C5—C6178.7 (2)C11—C12—C13—C80.6 (4)
  6 in total

1.  Coordination Compounds of Schiff-Base Ligands Derived from Diaminomaleonitrile (DMN): Mononuclear, Dinuclear, and Macrocyclic Derivatives.

Authors:  Mark J. MacLachlan; Murray K. Park; Laurence K. Thompson
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2.  A short history of SHELX.

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

3.  Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents.

Authors:  Shijun Ren; Rubin Wang; Kenichi Komatsu; Patricia Bonaz-Krause; Yegor Zyrianov; Charles E McKenna; Csaba Csipke; Zoltan A Tokes; Eric J Lien
Journal:  J Med Chem       Date:  2002-01-17       Impact factor: 7.446

Review 4.  Template-directed synthesis employing reversible imine bond formation.

Authors:  Cari D Meyer; C Steven Joiner; J Fraser Stoddart
Journal:  Chem Soc Rev       Date:  2007-11       Impact factor: 54.564

5.  N-[(E)-1,3-Benzodioxol-5-yl-methyl-idene]-4-methyl-aniline.

Authors:  M Nawaz Tahir; Hazoor Ahmad Shad; Muhammad Naeem Khan; Riaz H Tariq
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-24

6.  2-{[(E)-1,3-Benzodioxol-5-yl]methyl-idene-amino}-benzoic acid.

Authors:  M Nawaz Tahir; Hazoor Ahmad Shad; Muhammad Naeem Khan; Muhammad Ilyas Tariq
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-30
  6 in total

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