Literature DB >> 21754716

4,4'-Methylenebis{N-[(E)-quinolin-2-yl-methylidene]aniline}.

Daoud Djamel1, Douadi Tahar, Haffar Djahida, Hammani Hanane, Chafaa Salah.   

Abstract

The title compound, C(33)H(24)N(4), was prepared by the reaction of a bifunctional aromatic diamine (4,4'-diamino-diphenyl-methane) and an aldehyde (quinoline-2-carboxaldhyde). The mol-ecule consists of two nearly planar (or r.m.s. deviation = 0.017 Å) 4-methyl-N-[(E)-quinolin-2-yl-methyl-idene]aniline moieties, which are linked by the methyl-ene group. The angle between the mean planes of the two benzene rings connected to the methyl-ene group is 77.86 (11)°.

Entities:  

Year:  2011        PMID： 21754716      PMCID： PMC3120396          DOI： 10.1107/S1600536811016011

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


Related literature

For the biological and pharmacological activity of quinolines and their derivatives, see: Kidwai et al. (2000 ▶); Souza (2005 ▶); Musiol et al. (2006 ▶); Gómez-Barrio et al. (2006 ▶); Vinsova et al. (2008 ▶); Jain et al. (2005 ▶); Chen et al. (2006 ▶). For water treatment applications, see: Izatt et al. (1995 ▶); Kalcher et al. (1995 ▶); Gilmartin & Hart (1995 ▶). For use in corrosion inhibitors, see: Ahamad et al. (2010 ▶); Negm et al. (2010 ▶). For related structures, see: Girija et al. (2004 ▶); Gowda et al. (2007 ▶). For the synthesis, see: Issaadi et al. (2005 ▶); Ghames et al. (2006 ▶); Kaabi et al. (2007 ▶).

Experimental

Crystal data

C33H24N4 M = 476.56 Triclinic, a = 4.6051 (2) Å b = 6.0189 (2) Å c = 22.2172 (8) Å α = 88.393 (2)° β = 88.521 (2)° γ = 78.044 (2)° V = 602.09 (4) Å3 Z = 1 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.10 × 0.07 × 0.02 mm

Data collection

Bruker APEXII diffractometer 9094 measured reflections 2707 independent reflections 2415 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.087 S = 1.10 2707 reflections 335 parameters 3 restraints H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.16 e Å−3 Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016011/fy2004sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016011/fy2004Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811016011/fy2004Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C33H24N4F(000) = 250
Mr = 476.56Dx = 1.314 Mg m−3
Triclinic, P1Melting point: 472 K
a = 4.6051 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.0189 (2) ÅCell parameters from 3977 reflections
c = 22.2172 (8) Åθ = 2.8–27.4°
α = 88.393 (2)°µ = 0.08 mm−1
β = 88.521 (2)°T = 293 K
γ = 78.044 (2)°Plate, white
V = 602.09 (4) Å30.10 × 0.07 × 0.02 mm
Z = 1
Bruker APEXII diffractometer2415 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590Rint = 0.025
graphiteθmax = 27.4°, θmin = 3.5°
CCD rotation images, thick slices scansh = −5→5
9094 measured reflectionsk = −7→7
2707 independent reflectionsl = −28→28
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0373P)2 + 0.1098P] where P = (Fo2 + 2Fc2)/3
2707 reflections(Δ/σ)max = 0.001
335 parametersΔρmax = 0.21 e Å−3
3 restraintsΔρmin = −0.16 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
N10.6501 (4)0.5318 (3)0.77370 (8)0.0237 (4)
N21.0442 (4)0.6798 (3)0.89610 (8)0.0238 (4)
N41.0206 (4)−0.2145 (3)1.38522 (9)0.0268 (4)
C50.2926 (5)0.8583 (4)0.73373 (10)0.0253 (5)
C100.9472 (5)0.5623 (4)0.85769 (10)0.0247 (5)
H101.02070.40630.85690.03*
C241.3130 (5)−0.1462 (4)1.29921 (10)0.0278 (5)
H241.20050.00071.29570.033*
C171.9310 (5)0.3232 (4)1.07135 (10)0.0269 (5)
H17A1.99710.45041.08840.032*
H17B2.10150.22791.0520.032*
N31.5292 (4)−0.2108 (3)1.26316 (8)0.0276 (4)
C211.6114 (5)−0.0656 (4)1.21714 (10)0.0253 (5)
C290.9465 (5)−0.3569 (4)1.42954 (10)0.0248 (5)
C90.7206 (5)0.6683 (4)0.81435 (10)0.0228 (5)
C121.3477 (5)0.7218 (4)0.97880 (10)0.0258 (5)
H121.25860.87540.97770.031*
C60.4393 (5)0.6264 (4)0.73269 (10)0.0228 (5)
C111.2656 (4)0.5772 (4)0.93764 (9)0.0219 (5)
C251.2375 (5)−0.3021 (4)1.34684 (10)0.0258 (5)
C161.4071 (5)0.3483 (4)0.93972 (10)0.0251 (5)
H161.35650.24880.91250.03*
C281.0849 (5)−0.5901 (4)1.43483 (10)0.0265 (5)
C151.6231 (5)0.2676 (4)0.98216 (10)0.0250 (5)
H151.71680.11510.98260.03*
C221.8462 (5)−0.1645 (4)1.17962 (10)0.0272 (5)
H221.9367−0.31621.18590.033*
C40.0736 (5)0.9418 (4)0.69045 (11)0.0327 (5)
H4−0.02491.09320.69110.039*
C70.3754 (5)0.9952 (4)0.77817 (10)0.0296 (5)
H70.28311.14760.78040.035*
C80.5909 (5)0.9030 (4)0.81772 (10)0.0267 (5)
H80.65190.99230.84640.032*
C131.5611 (5)0.6402 (4)1.02157 (10)0.0262 (5)
H131.6110.73971.04890.031*
C330.9868 (5)−0.7265 (4)1.48092 (11)0.0309 (5)
H331.0742−0.881.48430.037*
C320.7644 (6)−0.6344 (4)1.52053 (11)0.0340 (6)
H320.702−0.72541.55060.041*
C300.7182 (5)−0.2664 (4)1.47154 (11)0.0301 (5)
H300.6277−0.11341.46890.036*
C10.3662 (5)0.4863 (4)0.68751 (10)0.0272 (5)
H10.46370.33490.68570.033*
C141.7009 (5)0.4130 (4)1.02415 (10)0.0237 (5)
C191.5822 (5)0.2860 (4)1.15999 (10)0.0273 (5)
H191.49270.4381.15370.033*
C231.9483 (5)−0.0403 (4)1.13279 (11)0.0286 (5)
H232.1062−0.10981.10830.034*
C30.0056 (5)0.8029 (5)0.64793 (12)0.0359 (6)
H3−0.13850.86010.61980.043*
C20.1522 (5)0.5731 (4)0.64641 (11)0.0322 (5)
H20.10370.47950.61730.039*
C181.8167 (5)0.1865 (4)1.12220 (10)0.0240 (5)
C271.3166 (5)−0.6745 (4)1.39298 (10)0.0304 (5)
H271.4141−0.8261.39510.036*
C261.3957 (5)−0.5313 (4)1.34953 (10)0.0287 (5)
H261.5499−0.5831.32230.034*
C201.4791 (5)0.1629 (4)1.20683 (10)0.0276 (5)
H201.32180.23261.23140.033*
C310.6299 (5)−0.4020 (4)1.51582 (11)0.0333 (5)
H310.4799−0.34041.5430.04*
U11U22U33U12U13U23
N10.0219 (9)0.0260 (9)0.0232 (9)−0.0050 (8)0.0006 (7)−0.0012 (7)
N20.0213 (9)0.0274 (10)0.0233 (9)−0.0064 (8)0.0020 (7)−0.0009 (7)
N40.0286 (10)0.0285 (10)0.0242 (10)−0.0084 (8)−0.0018 (8)0.0014 (8)
C50.0194 (11)0.0292 (12)0.0257 (11)−0.0026 (9)0.0053 (9)0.0032 (9)
C100.0232 (11)0.0251 (11)0.0245 (11)−0.0025 (9)0.0016 (9)−0.0010 (9)
C240.0323 (13)0.0281 (11)0.0241 (11)−0.0085 (10)−0.0032 (10)0.0005 (9)
C170.0204 (11)0.0363 (13)0.0259 (11)−0.0107 (10)−0.0012 (9)0.0023 (10)
N30.0275 (11)0.0335 (11)0.0222 (10)−0.0072 (9)−0.0013 (8)0.0007 (8)
C210.0258 (12)0.0319 (12)0.0203 (11)−0.0097 (10)−0.0038 (9)−0.0018 (9)
C290.0239 (11)0.0304 (12)0.0217 (11)−0.0090 (9)−0.0054 (9)0.0014 (9)
C90.0195 (11)0.0278 (12)0.0210 (10)−0.0051 (9)0.0048 (9)0.0007 (9)
C120.0229 (11)0.0246 (11)0.0301 (12)−0.0055 (9)0.0025 (9)−0.0042 (9)
C60.0185 (11)0.0269 (12)0.0230 (11)−0.0056 (9)0.0055 (8)0.0025 (9)
C110.0196 (11)0.0276 (12)0.0196 (10)−0.0079 (9)0.0028 (8)−0.0010 (9)
C250.0299 (12)0.0303 (12)0.0195 (10)−0.0109 (10)−0.0045 (9)0.0002 (9)
C160.0258 (12)0.0281 (12)0.0225 (11)−0.0074 (9)0.0016 (9)−0.0052 (9)
C280.0286 (12)0.0291 (12)0.0240 (11)−0.0101 (9)−0.0066 (9)0.0000 (9)
C150.0222 (11)0.0259 (11)0.0265 (11)−0.0038 (9)0.0006 (9)−0.0007 (9)
C220.0261 (12)0.0281 (12)0.0265 (12)−0.0036 (9)−0.0007 (10)−0.0017 (9)
C40.0241 (12)0.0336 (13)0.0367 (13)0.0010 (10)0.0018 (10)0.0072 (10)
C70.0297 (13)0.0248 (12)0.0313 (12)0.0001 (10)0.0067 (10)−0.0004 (9)
C80.0301 (12)0.0265 (11)0.0229 (11)−0.0043 (9)0.0038 (9)−0.0046 (9)
C130.0238 (11)0.0331 (13)0.0239 (11)−0.0105 (10)0.0005 (9)−0.0055 (9)
C330.0335 (14)0.0297 (12)0.0311 (13)−0.0101 (11)−0.0069 (10)0.0057 (10)
C320.0382 (14)0.0379 (13)0.0296 (12)−0.0175 (11)−0.0027 (10)0.0092 (10)
C300.0290 (12)0.0337 (12)0.0283 (11)−0.0075 (10)−0.0024 (9)0.0005 (9)
C10.0253 (11)0.0307 (12)0.0259 (11)−0.0072 (9)0.0015 (9)0.0008 (9)
C140.0170 (10)0.0346 (13)0.0210 (10)−0.0094 (9)0.0046 (8)0.0017 (9)
C190.0260 (12)0.0300 (12)0.0258 (11)−0.0060 (9)−0.0024 (9)0.0015 (9)
C230.0233 (11)0.0365 (13)0.0263 (11)−0.0063 (10)0.0040 (9)−0.0075 (10)
C30.0251 (12)0.0507 (16)0.0315 (12)−0.0080 (11)−0.0064 (10)0.0125 (11)
C20.0289 (12)0.0443 (14)0.0262 (12)−0.0145 (11)−0.0013 (9)0.0013 (10)
C180.0175 (10)0.0363 (12)0.0201 (10)−0.0098 (9)−0.0032 (8)−0.0013 (9)
C270.0349 (13)0.0259 (11)0.0294 (12)−0.0033 (10)−0.0062 (10)−0.0006 (9)
C260.0315 (12)0.0321 (12)0.0218 (10)−0.0049 (10)−0.0005 (9)−0.0030 (9)
C200.0240 (11)0.0347 (12)0.0233 (11)−0.0043 (9)0.0020 (9)−0.0021 (9)
C310.0302 (13)0.0433 (14)0.0283 (12)−0.0124 (11)0.0005 (10)−0.0003 (10)
N1—C91.328 (3)C28—C331.418 (3)
N1—C61.373 (3)C15—C141.399 (3)
N2—C101.270 (3)C15—H150.93
N2—C111.424 (3)C22—C231.393 (3)
N4—C251.329 (3)C22—H220.93
N4—C291.370 (3)C4—C31.363 (4)
C5—C71.412 (3)C4—H40.93
C5—C41.417 (3)C7—C81.362 (3)
C5—C61.420 (3)C7—H70.93
C10—C91.471 (3)C8—H80.93
C10—H100.93C13—C141.386 (3)
C24—N31.265 (3)C13—H130.93
C24—C251.477 (3)C33—C321.370 (4)
C24—H240.93C33—H330.93
C17—C141.517 (3)C32—C311.409 (4)
C17—C181.526 (3)C32—H320.93
C17—H17A0.97C30—C311.368 (3)
C17—H17B0.97C30—H300.93
N3—C211.421 (3)C1—C21.373 (3)
C21—C221.390 (3)C1—H10.93
C21—C201.399 (3)C19—C201.391 (3)
C29—C301.419 (3)C19—C181.394 (3)
C29—C281.419 (3)C19—H190.93
C9—C81.418 (3)C23—C181.390 (3)
C12—C131.390 (3)C23—H230.93
C12—C111.392 (3)C3—C21.408 (4)
C12—H120.93C3—H30.93
C6—C11.419 (3)C2—H20.93
C11—C161.397 (3)C27—C261.368 (3)
C25—C261.421 (3)C27—H270.93
C16—C151.392 (3)C26—H260.93
C16—H160.93C20—H200.93
C28—C271.418 (3)C31—H310.93
C9—N1—C6117.22 (19)C3—C4—H4119.6
C10—N2—C11121.13 (17)C5—C4—H4119.6
C25—N4—C29117.13 (19)C8—C7—C5119.7 (2)
C7—C5—C4123.2 (2)C8—C7—H7120.1
C7—C5—C6117.7 (2)C5—C7—H7120.1
C4—C5—C6119.1 (2)C7—C8—C9118.8 (2)
N2—C10—C9121.21 (18)C7—C8—H8120.6
N2—C10—H10119.4C9—C8—H8120.6
C9—C10—H10119.4C14—C13—C12121.1 (2)
N3—C24—C25120.6 (2)C14—C13—H13119.4
N3—C24—H24119.7C12—C13—H13119.4
C25—C24—H24119.7C32—C33—C28120.6 (2)
C14—C17—C18113.55 (17)C32—C33—H33119.7
C14—C17—H17A108.9C28—C33—H33119.7
C18—C17—H17A108.9C33—C32—C31120.2 (2)
C14—C17—H17B108.9C33—C32—H32119.9
C18—C17—H17B108.9C31—C32—H32119.9
H17A—C17—H17B107.7C31—C30—C29120.7 (2)
C24—N3—C21122.4 (2)C31—C30—H30119.7
C22—C21—C20118.4 (2)C29—C30—H30119.7
C22—C21—N3115.5 (2)C2—C1—C6120.3 (2)
C20—C21—N3126.1 (2)C2—C1—H1119.8
N4—C29—C30118.1 (2)C6—C1—H1119.8
N4—C29—C28123.1 (2)C13—C14—C15118.2 (2)
C30—C29—C28118.8 (2)C13—C14—C17121.1 (2)
N1—C9—C8124.0 (2)C15—C14—C17120.7 (2)
N1—C9—C10116.01 (18)C20—C19—C18121.4 (2)
C8—C9—C10120.03 (18)C20—C19—H19119.3
C13—C12—C11121.0 (2)C18—C19—H19119.3
C13—C12—H12119.5C18—C23—C22120.7 (2)
C11—C12—H12119.5C18—C23—H23119.7
N1—C6—C5122.56 (19)C22—C23—H23119.7
N1—C6—C1118.5 (2)C4—C3—C2120.4 (2)
C5—C6—C1118.9 (2)C4—C3—H3119.8
C12—C11—C16118.22 (19)C2—C3—H3119.8
C12—C11—N2115.96 (19)C1—C2—C3120.5 (2)
C16—C11—N2125.81 (18)C1—C2—H2119.7
N4—C25—C26124.0 (2)C3—C2—H2119.7
N4—C25—C24116.30 (19)C23—C18—C19118.2 (2)
C26—C25—C24119.7 (2)C23—C18—C17120.7 (2)
C15—C16—C11120.7 (2)C19—C18—C17121.1 (2)
C15—C16—H16119.7C26—C27—C28119.5 (2)
C11—C16—H16119.7C26—C27—H27120.2
C27—C28—C33123.3 (2)C28—C27—H27120.2
C27—C28—C29117.5 (2)C27—C26—C25118.7 (2)
C33—C28—C29119.2 (2)C27—C26—H26120.6
C16—C15—C14120.9 (2)C25—C26—H26120.6
C16—C15—H15119.6C19—C20—C21120.2 (2)
C14—C15—H15119.6C19—C20—H20119.9
C21—C22—C23121.1 (2)C21—C20—H20119.9
C21—C22—H22119.4C30—C31—C32120.5 (2)
C23—C22—H22119.4C30—C31—H31119.7
C3—C4—C5120.8 (2)C32—C31—H31119.7
  7 in total

1.  Alumina-supported synthesis of antibacterial quinolines using microwaves.

Authors:  M Kidwai; K R Bhushan; P Sapra; R K Saxena; R Gupta
Journal:  Bioorg Med Chem       Date:  2000-01       Impact factor: 3.641

Review 2.  New fluoroquinolones: a class of potent antibiotics.

Authors:  Marcus Vinícius Nora De Souza
Journal:  Mini Rev Med Chem       Date:  2005-11       Impact factor: 3.862

3.  A short history of SHELX.

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

Review 4.  Sensing with chemically and biologically modified carbon electrodes. A review.

Authors:  M A Gilmartin; J P Hart
Journal:  Analyst       Date:  1995-04       Impact factor: 4.616

5.  Antifungal properties of new series of quinoline derivatives.

Authors:  Robert Musiol; Josef Jampilek; Vladimir Buchta; Luis Silva; Halina Niedbala; Barbara Podeszwa; Anna Palka; Katarzyna Majerz-Maniecka; Barbara Oleksyn; Jaroslaw Polanski
Journal:  Bioorg Med Chem       Date:  2006-02-03       Impact factor: 3.641

6.  Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues.

Authors:  Meenakshi Jain; Shabana I Khan; Babu L Tekwani; Melissa R Jacob; Savita Singh; Prati Pal Singh; Rahul Jain
Journal:  Bioorg Med Chem       Date:  2005-07-15       Impact factor: 3.641

7.  Synthesis, cytotoxicity, and anti-inflammatory evaluation of 2-(furan-2-yl)-4-(phenoxy)quinoline derivatives. Part 4.

Authors:  Yeh-Long Chen; Yue-Ling Zhao; Chih-Ming Lu; Cherng-Chyi Tzeng; Jih-Pyang Wang
Journal:  Bioorg Med Chem       Date:  2006-03-09       Impact factor: 3.641
  7 in total

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