organic compounds
4,4′-Methylenebis{N-[(E)-quinolin-2-ylmethylidene]aniline}
aLaboratoire d'Électrochimie des Matériaux Moléculaires et Complexes, (LEMMC), Département de Génie des Procèdes Faculté de Technologie, Université Ferhat Abbas, Setif 19000, Algeria
*Correspondence e-mail: daoudkamal88@yahoo.fr
The title compound, C33H24N4, was prepared by the reaction of a bifunctional aromatic diamine (4,4′-diaminodiphenylmethane) and an aldehyde (quinoline-2-carboxaldhyde). The molecule consists of two nearly planar (or r.m.s. deviation = 0.017 Å) 4-methyl-N-[(E)-quinolin-2-ylmethylidene]aniline moieties, which are linked by the methylene group. The angle between the mean planes of the two benzene rings connected to the methylene group is 77.86 (11)°.
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
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Data collection: APEX2 (Bruker, 2002); cell 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).
Supporting information
10.1107/S1600536811016011/fy2004sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811016011/fy2004Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811016011/fy2004Isup3.cml
The studied Schiff base compound was synthesized, as reported in the literature (Issaadi et al., 2005; Ghames et al., 2006; Kaabi et al., 2007), by reacting the mixture of 4,4'-Diaminodiphenyl methane (0.396 mg, 0.002 mol) and 2-quinolinecarboxaldhyde (0.64 mg, 0.004 mol) in 20 ml of boiling ethanol for 5 h. After completion of the reaction the separated solid was filtered, washed with alcohol, and finally recrystallized from ethanol and dried under vacuum. The single crystals suitable for X-ray analysis were obtained by slow evaporation from ethanol-dichloromethane (1:1).
H atoms were included in geometric positions with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C) and were refined in riding mode. In the absence of significant
Friedel opposites were merged.Data collection: APEX2 (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).Fig. 1. The title molecule with displacement ellipsoids for non–H atoms drawn at the 50% probability level. |
C33H24N4 | F(000) = 250 |
Mr = 476.56 | Dx = 1.314 Mg m−3 |
Triclinic, P1 | Melting point: 472 K |
a = 4.6051 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.0189 (2) Å | Cell parameters from 3977 reflections |
c = 22.2172 (8) Å | θ = 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) Å3 | 0.10 × 0.07 × 0.02 mm |
Z = 1 |
Bruker APEXII diffractometer | 2415 reflections with I > 2σ(I) |
Radiation source: Enraf Nonius FR590 | Rint = 0.025 |
Graphite monochromator | θmax = 27.4°, θmin = 3.5° |
CCD rotation images, thick slices scans | h = −5→5 |
9094 measured reflections | k = −7→7 |
2707 independent reflections | l = −28→28 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0373P)2 + 0.1098P] where P = (Fo2 + 2Fc2)/3 |
2707 reflections | (Δ/σ)max = 0.001 |
335 parameters | Δρmax = 0.21 e Å−3 |
3 restraints | Δρmin = −0.16 e Å−3 |
C33H24N4 | γ = 78.044 (2)° |
Mr = 476.56 | V = 602.09 (4) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.6051 (2) Å | Mo Kα radiation |
b = 6.0189 (2) Å | µ = 0.08 mm−1 |
c = 22.2172 (8) Å | T = 293 K |
α = 88.393 (2)° | 0.10 × 0.07 × 0.02 mm |
β = 88.521 (2)° |
Bruker APEXII diffractometer | 2415 reflections with I > 2σ(I) |
9094 measured reflections | Rint = 0.025 |
2707 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | 3 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.21 e Å−3 |
2707 reflections | Δρmin = −0.16 e Å−3 |
335 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6501 (4) | 0.5318 (3) | 0.77370 (8) | 0.0237 (4) | |
N2 | 1.0442 (4) | 0.6798 (3) | 0.89610 (8) | 0.0238 (4) | |
N4 | 1.0206 (4) | −0.2145 (3) | 1.38522 (9) | 0.0268 (4) | |
C5 | 0.2926 (5) | 0.8583 (4) | 0.73373 (10) | 0.0253 (5) | |
C10 | 0.9472 (5) | 0.5623 (4) | 0.85769 (10) | 0.0247 (5) | |
H10 | 1.0207 | 0.4063 | 0.8569 | 0.03* | |
C24 | 1.3130 (5) | −0.1462 (4) | 1.29921 (10) | 0.0278 (5) | |
H24 | 1.2005 | 0.0007 | 1.2957 | 0.033* | |
C17 | 1.9310 (5) | 0.3232 (4) | 1.07135 (10) | 0.0269 (5) | |
H17A | 1.9971 | 0.4504 | 1.0884 | 0.032* | |
H17B | 2.1015 | 0.2279 | 1.052 | 0.032* | |
N3 | 1.5292 (4) | −0.2108 (3) | 1.26316 (8) | 0.0276 (4) | |
C21 | 1.6114 (5) | −0.0656 (4) | 1.21714 (10) | 0.0253 (5) | |
C29 | 0.9465 (5) | −0.3569 (4) | 1.42954 (10) | 0.0248 (5) | |
C9 | 0.7206 (5) | 0.6683 (4) | 0.81435 (10) | 0.0228 (5) | |
C12 | 1.3477 (5) | 0.7218 (4) | 0.97880 (10) | 0.0258 (5) | |
H12 | 1.2586 | 0.8754 | 0.9777 | 0.031* | |
C6 | 0.4393 (5) | 0.6264 (4) | 0.73269 (10) | 0.0228 (5) | |
C11 | 1.2656 (4) | 0.5772 (4) | 0.93764 (9) | 0.0219 (5) | |
C25 | 1.2375 (5) | −0.3021 (4) | 1.34684 (10) | 0.0258 (5) | |
C16 | 1.4071 (5) | 0.3483 (4) | 0.93972 (10) | 0.0251 (5) | |
H16 | 1.3565 | 0.2488 | 0.9125 | 0.03* | |
C28 | 1.0849 (5) | −0.5901 (4) | 1.43483 (10) | 0.0265 (5) | |
C15 | 1.6231 (5) | 0.2676 (4) | 0.98216 (10) | 0.0250 (5) | |
H15 | 1.7168 | 0.1151 | 0.9826 | 0.03* | |
C22 | 1.8462 (5) | −0.1645 (4) | 1.17962 (10) | 0.0272 (5) | |
H22 | 1.9367 | −0.3162 | 1.1859 | 0.033* | |
C4 | 0.0736 (5) | 0.9418 (4) | 0.69045 (11) | 0.0327 (5) | |
H4 | −0.0249 | 1.0932 | 0.6911 | 0.039* | |
C7 | 0.3754 (5) | 0.9952 (4) | 0.77817 (10) | 0.0296 (5) | |
H7 | 0.2831 | 1.1476 | 0.7804 | 0.035* | |
C8 | 0.5909 (5) | 0.9030 (4) | 0.81772 (10) | 0.0267 (5) | |
H8 | 0.6519 | 0.9923 | 0.8464 | 0.032* | |
C13 | 1.5611 (5) | 0.6402 (4) | 1.02157 (10) | 0.0262 (5) | |
H13 | 1.611 | 0.7397 | 1.0489 | 0.031* | |
C33 | 0.9868 (5) | −0.7265 (4) | 1.48092 (11) | 0.0309 (5) | |
H33 | 1.0742 | −0.88 | 1.4843 | 0.037* | |
C32 | 0.7644 (6) | −0.6344 (4) | 1.52053 (11) | 0.0340 (6) | |
H32 | 0.702 | −0.7254 | 1.5506 | 0.041* | |
C30 | 0.7182 (5) | −0.2664 (4) | 1.47154 (11) | 0.0301 (5) | |
H30 | 0.6277 | −0.1134 | 1.4689 | 0.036* | |
C1 | 0.3662 (5) | 0.4863 (4) | 0.68751 (10) | 0.0272 (5) | |
H1 | 0.4637 | 0.3349 | 0.6857 | 0.033* | |
C14 | 1.7009 (5) | 0.4130 (4) | 1.02415 (10) | 0.0237 (5) | |
C19 | 1.5822 (5) | 0.2860 (4) | 1.15999 (10) | 0.0273 (5) | |
H19 | 1.4927 | 0.438 | 1.1537 | 0.033* | |
C23 | 1.9483 (5) | −0.0403 (4) | 1.13279 (11) | 0.0286 (5) | |
H23 | 2.1062 | −0.1098 | 1.1083 | 0.034* | |
C3 | 0.0056 (5) | 0.8029 (5) | 0.64793 (12) | 0.0359 (6) | |
H3 | −0.1385 | 0.8601 | 0.6198 | 0.043* | |
C2 | 0.1522 (5) | 0.5731 (4) | 0.64641 (11) | 0.0322 (5) | |
H2 | 0.1037 | 0.4795 | 0.6173 | 0.039* | |
C18 | 1.8167 (5) | 0.1865 (4) | 1.12220 (10) | 0.0240 (5) | |
C27 | 1.3166 (5) | −0.6745 (4) | 1.39298 (10) | 0.0304 (5) | |
H27 | 1.4141 | −0.826 | 1.3951 | 0.036* | |
C26 | 1.3957 (5) | −0.5313 (4) | 1.34953 (10) | 0.0287 (5) | |
H26 | 1.5499 | −0.583 | 1.3223 | 0.034* | |
C20 | 1.4791 (5) | 0.1629 (4) | 1.20683 (10) | 0.0276 (5) | |
H20 | 1.3218 | 0.2326 | 1.2314 | 0.033* | |
C31 | 0.6299 (5) | −0.4020 (4) | 1.51582 (11) | 0.0333 (5) | |
H31 | 0.4799 | −0.3404 | 1.543 | 0.04* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0219 (9) | 0.0260 (9) | 0.0232 (9) | −0.0050 (8) | 0.0006 (7) | −0.0012 (7) |
N2 | 0.0213 (9) | 0.0274 (10) | 0.0233 (9) | −0.0064 (8) | 0.0020 (7) | −0.0009 (7) |
N4 | 0.0286 (10) | 0.0285 (10) | 0.0242 (10) | −0.0084 (8) | −0.0018 (8) | 0.0014 (8) |
C5 | 0.0194 (11) | 0.0292 (12) | 0.0257 (11) | −0.0026 (9) | 0.0053 (9) | 0.0032 (9) |
C10 | 0.0232 (11) | 0.0251 (11) | 0.0245 (11) | −0.0025 (9) | 0.0016 (9) | −0.0010 (9) |
C24 | 0.0323 (13) | 0.0281 (11) | 0.0241 (11) | −0.0085 (10) | −0.0032 (10) | 0.0005 (9) |
C17 | 0.0204 (11) | 0.0363 (13) | 0.0259 (11) | −0.0107 (10) | −0.0012 (9) | 0.0023 (10) |
N3 | 0.0275 (11) | 0.0335 (11) | 0.0222 (10) | −0.0072 (9) | −0.0013 (8) | 0.0007 (8) |
C21 | 0.0258 (12) | 0.0319 (12) | 0.0203 (11) | −0.0097 (10) | −0.0038 (9) | −0.0018 (9) |
C29 | 0.0239 (11) | 0.0304 (12) | 0.0217 (11) | −0.0090 (9) | −0.0054 (9) | 0.0014 (9) |
C9 | 0.0195 (11) | 0.0278 (12) | 0.0210 (10) | −0.0051 (9) | 0.0048 (9) | 0.0007 (9) |
C12 | 0.0229 (11) | 0.0246 (11) | 0.0301 (12) | −0.0055 (9) | 0.0025 (9) | −0.0042 (9) |
C6 | 0.0185 (11) | 0.0269 (12) | 0.0230 (11) | −0.0056 (9) | 0.0055 (8) | 0.0025 (9) |
C11 | 0.0196 (11) | 0.0276 (12) | 0.0196 (10) | −0.0079 (9) | 0.0028 (8) | −0.0010 (9) |
C25 | 0.0299 (12) | 0.0303 (12) | 0.0195 (10) | −0.0109 (10) | −0.0045 (9) | 0.0002 (9) |
C16 | 0.0258 (12) | 0.0281 (12) | 0.0225 (11) | −0.0074 (9) | 0.0016 (9) | −0.0052 (9) |
C28 | 0.0286 (12) | 0.0291 (12) | 0.0240 (11) | −0.0101 (9) | −0.0066 (9) | 0.0000 (9) |
C15 | 0.0222 (11) | 0.0259 (11) | 0.0265 (11) | −0.0038 (9) | 0.0006 (9) | −0.0007 (9) |
C22 | 0.0261 (12) | 0.0281 (12) | 0.0265 (12) | −0.0036 (9) | −0.0007 (10) | −0.0017 (9) |
C4 | 0.0241 (12) | 0.0336 (13) | 0.0367 (13) | 0.0010 (10) | 0.0018 (10) | 0.0072 (10) |
C7 | 0.0297 (13) | 0.0248 (12) | 0.0313 (12) | 0.0001 (10) | 0.0067 (10) | −0.0004 (9) |
C8 | 0.0301 (12) | 0.0265 (11) | 0.0229 (11) | −0.0043 (9) | 0.0038 (9) | −0.0046 (9) |
C13 | 0.0238 (11) | 0.0331 (13) | 0.0239 (11) | −0.0105 (10) | 0.0005 (9) | −0.0055 (9) |
C33 | 0.0335 (14) | 0.0297 (12) | 0.0311 (13) | −0.0101 (11) | −0.0069 (10) | 0.0057 (10) |
C32 | 0.0382 (14) | 0.0379 (13) | 0.0296 (12) | −0.0175 (11) | −0.0027 (10) | 0.0092 (10) |
C30 | 0.0290 (12) | 0.0337 (12) | 0.0283 (11) | −0.0075 (10) | −0.0024 (9) | 0.0005 (9) |
C1 | 0.0253 (11) | 0.0307 (12) | 0.0259 (11) | −0.0072 (9) | 0.0015 (9) | 0.0008 (9) |
C14 | 0.0170 (10) | 0.0346 (13) | 0.0210 (10) | −0.0094 (9) | 0.0046 (8) | 0.0017 (9) |
C19 | 0.0260 (12) | 0.0300 (12) | 0.0258 (11) | −0.0060 (9) | −0.0024 (9) | 0.0015 (9) |
C23 | 0.0233 (11) | 0.0365 (13) | 0.0263 (11) | −0.0063 (10) | 0.0040 (9) | −0.0075 (10) |
C3 | 0.0251 (12) | 0.0507 (16) | 0.0315 (12) | −0.0080 (11) | −0.0064 (10) | 0.0125 (11) |
C2 | 0.0289 (12) | 0.0443 (14) | 0.0262 (12) | −0.0145 (11) | −0.0013 (9) | 0.0013 (10) |
C18 | 0.0175 (10) | 0.0363 (12) | 0.0201 (10) | −0.0098 (9) | −0.0032 (8) | −0.0013 (9) |
C27 | 0.0349 (13) | 0.0259 (11) | 0.0294 (12) | −0.0033 (10) | −0.0062 (10) | −0.0006 (9) |
C26 | 0.0315 (12) | 0.0321 (12) | 0.0218 (10) | −0.0049 (10) | −0.0005 (9) | −0.0030 (9) |
C20 | 0.0240 (11) | 0.0347 (12) | 0.0233 (11) | −0.0043 (9) | 0.0020 (9) | −0.0021 (9) |
C31 | 0.0302 (13) | 0.0433 (14) | 0.0283 (12) | −0.0124 (11) | 0.0005 (10) | −0.0003 (10) |
N1—C9 | 1.328 (3) | C28—C33 | 1.418 (3) |
N1—C6 | 1.373 (3) | C15—C14 | 1.399 (3) |
N2—C10 | 1.270 (3) | C15—H15 | 0.93 |
N2—C11 | 1.424 (3) | C22—C23 | 1.393 (3) |
N4—C25 | 1.329 (3) | C22—H22 | 0.93 |
N4—C29 | 1.370 (3) | C4—C3 | 1.363 (4) |
C5—C7 | 1.412 (3) | C4—H4 | 0.93 |
C5—C4 | 1.417 (3) | C7—C8 | 1.362 (3) |
C5—C6 | 1.420 (3) | C7—H7 | 0.93 |
C10—C9 | 1.471 (3) | C8—H8 | 0.93 |
C10—H10 | 0.93 | C13—C14 | 1.386 (3) |
C24—N3 | 1.265 (3) | C13—H13 | 0.93 |
C24—C25 | 1.477 (3) | C33—C32 | 1.370 (4) |
C24—H24 | 0.93 | C33—H33 | 0.93 |
C17—C14 | 1.517 (3) | C32—C31 | 1.409 (4) |
C17—C18 | 1.526 (3) | C32—H32 | 0.93 |
C17—H17A | 0.97 | C30—C31 | 1.368 (3) |
C17—H17B | 0.97 | C30—H30 | 0.93 |
N3—C21 | 1.421 (3) | C1—C2 | 1.373 (3) |
C21—C22 | 1.390 (3) | C1—H1 | 0.93 |
C21—C20 | 1.399 (3) | C19—C20 | 1.391 (3) |
C29—C30 | 1.419 (3) | C19—C18 | 1.394 (3) |
C29—C28 | 1.419 (3) | C19—H19 | 0.93 |
C9—C8 | 1.418 (3) | C23—C18 | 1.390 (3) |
C12—C13 | 1.390 (3) | C23—H23 | 0.93 |
C12—C11 | 1.392 (3) | C3—C2 | 1.408 (4) |
C12—H12 | 0.93 | C3—H3 | 0.93 |
C6—C1 | 1.419 (3) | C2—H2 | 0.93 |
C11—C16 | 1.397 (3) | C27—C26 | 1.368 (3) |
C25—C26 | 1.421 (3) | C27—H27 | 0.93 |
C16—C15 | 1.392 (3) | C26—H26 | 0.93 |
C16—H16 | 0.93 | C20—H20 | 0.93 |
C28—C27 | 1.418 (3) | C31—H31 | 0.93 |
C9—N1—C6 | 117.22 (19) | C3—C4—H4 | 119.6 |
C10—N2—C11 | 121.13 (17) | C5—C4—H4 | 119.6 |
C25—N4—C29 | 117.13 (19) | C8—C7—C5 | 119.7 (2) |
C7—C5—C4 | 123.2 (2) | C8—C7—H7 | 120.1 |
C7—C5—C6 | 117.7 (2) | C5—C7—H7 | 120.1 |
C4—C5—C6 | 119.1 (2) | C7—C8—C9 | 118.8 (2) |
N2—C10—C9 | 121.21 (18) | C7—C8—H8 | 120.6 |
N2—C10—H10 | 119.4 | C9—C8—H8 | 120.6 |
C9—C10—H10 | 119.4 | C14—C13—C12 | 121.1 (2) |
N3—C24—C25 | 120.6 (2) | C14—C13—H13 | 119.4 |
N3—C24—H24 | 119.7 | C12—C13—H13 | 119.4 |
C25—C24—H24 | 119.7 | C32—C33—C28 | 120.6 (2) |
C14—C17—C18 | 113.55 (17) | C32—C33—H33 | 119.7 |
C14—C17—H17A | 108.9 | C28—C33—H33 | 119.7 |
C18—C17—H17A | 108.9 | C33—C32—C31 | 120.2 (2) |
C14—C17—H17B | 108.9 | C33—C32—H32 | 119.9 |
C18—C17—H17B | 108.9 | C31—C32—H32 | 119.9 |
H17A—C17—H17B | 107.7 | C31—C30—C29 | 120.7 (2) |
C24—N3—C21 | 122.4 (2) | C31—C30—H30 | 119.7 |
C22—C21—C20 | 118.4 (2) | C29—C30—H30 | 119.7 |
C22—C21—N3 | 115.5 (2) | C2—C1—C6 | 120.3 (2) |
C20—C21—N3 | 126.1 (2) | C2—C1—H1 | 119.8 |
N4—C29—C30 | 118.1 (2) | C6—C1—H1 | 119.8 |
N4—C29—C28 | 123.1 (2) | C13—C14—C15 | 118.2 (2) |
C30—C29—C28 | 118.8 (2) | C13—C14—C17 | 121.1 (2) |
N1—C9—C8 | 124.0 (2) | C15—C14—C17 | 120.7 (2) |
N1—C9—C10 | 116.01 (18) | C20—C19—C18 | 121.4 (2) |
C8—C9—C10 | 120.03 (18) | C20—C19—H19 | 119.3 |
C13—C12—C11 | 121.0 (2) | C18—C19—H19 | 119.3 |
C13—C12—H12 | 119.5 | C18—C23—C22 | 120.7 (2) |
C11—C12—H12 | 119.5 | C18—C23—H23 | 119.7 |
N1—C6—C5 | 122.56 (19) | C22—C23—H23 | 119.7 |
N1—C6—C1 | 118.5 (2) | C4—C3—C2 | 120.4 (2) |
C5—C6—C1 | 118.9 (2) | C4—C3—H3 | 119.8 |
C12—C11—C16 | 118.22 (19) | C2—C3—H3 | 119.8 |
C12—C11—N2 | 115.96 (19) | C1—C2—C3 | 120.5 (2) |
C16—C11—N2 | 125.81 (18) | C1—C2—H2 | 119.7 |
N4—C25—C26 | 124.0 (2) | C3—C2—H2 | 119.7 |
N4—C25—C24 | 116.30 (19) | C23—C18—C19 | 118.2 (2) |
C26—C25—C24 | 119.7 (2) | C23—C18—C17 | 120.7 (2) |
C15—C16—C11 | 120.7 (2) | C19—C18—C17 | 121.1 (2) |
C15—C16—H16 | 119.7 | C26—C27—C28 | 119.5 (2) |
C11—C16—H16 | 119.7 | C26—C27—H27 | 120.2 |
C27—C28—C33 | 123.3 (2) | C28—C27—H27 | 120.2 |
C27—C28—C29 | 117.5 (2) | C27—C26—C25 | 118.7 (2) |
C33—C28—C29 | 119.2 (2) | C27—C26—H26 | 120.6 |
C16—C15—C14 | 120.9 (2) | C25—C26—H26 | 120.6 |
C16—C15—H15 | 119.6 | C19—C20—C21 | 120.2 (2) |
C14—C15—H15 | 119.6 | C19—C20—H20 | 119.9 |
C21—C22—C23 | 121.1 (2) | C21—C20—H20 | 119.9 |
C21—C22—H22 | 119.4 | C30—C31—C32 | 120.5 (2) |
C23—C22—H22 | 119.4 | C30—C31—H31 | 119.7 |
C3—C4—C5 | 120.8 (2) | C32—C31—H31 | 119.7 |
Experimental details
Crystal data | |
Chemical formula | C33H24N4 |
Mr | 476.56 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 4.6051 (2), 6.0189 (2), 22.2172 (8) |
α, β, γ (°) | 88.393 (2), 88.521 (2), 78.044 (2) |
V (Å3) | 602.09 (4) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.10 × 0.07 × 0.02 |
Data collection | |
Diffractometer | Bruker APEXII diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9094, 2707, 2415 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.087, 1.10 |
No. of reflections | 2707 |
No. of parameters | 335 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.16 |
Computer programs: APEX2 (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Acknowledgements
The authors thanks Dr Lahcène Ouahab for the data collection at the Centre de Diffractomtétrie de l'Université de Rennes 1 CDiFX.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Quinolines and their derivatives are often used for the desig of synthetic compounds with diverse pharmacological and medicinal proprieties. Substituted quinolines have been reported in the literature to show antibacterial (Kidwai et al., 2000), antimalarial (Souza et al., 2005), antifungal (Musiol et al., 2006), antiparasitical (Gómez-Barrio et al., 2006), antimycobacterial (Vinsova et al., 2008), antileishmanial (Jain et al., 2005), and anti-inflammatory behavior (Chen et al., 2006). Schiff base compounds are typically formed by condensation of an aromatic diamine and a quinolinealdehyde. These kinds of compounds have a wide variety of applications in many fields. For example, their capacity for complexation of transition metals is useful in water treatment (Izatt et al., 1995; Kalcher et al., 1995; Gilmartin et al., 1995). They also serve as intermediates in certain enzymatic reactions and their use as corrosion inhibitors (Ahamad et al., 2010; Negm et al., 2010) shows their importance. The title compound, C33H24N4, is a condensation product of quinolinealdehyde with a bifunctional aromatic diamine. The two 4-methyl-N-[(E)-quinolin-2-ylmethylidene]aniline moieties are nearly planar. A dihedral angle of 77.86 (11)° is found between the mean planes of the benzene rings C11—C12—C13—C14—C15—C16 and C18—C19—C20—C21—C22—C23. The dihedral angle between the mean planes of the attached benzene and quinoline rings is 2.66 (9)° for the groups linked via N2 and 2.57 (9)° for those linked via N3. The corresponding bond lengths and bond angles are similar in both 4-methyl-N-[(E)-quinolin-2-ylmethylidene]aniline moieties. The N2—C10 imine (C=N) bond length of 1.270 (3) Å agrees with similar double bonds usually observed in related compounds (Girija et al., 2004), and it is much shorter than the N2—C11 single C—N bond of 1.425 (2) Å (Gowda et al., 2007).