4,4′-Methylenebis{N-[(E)-quinolin-2-yl­methylidene]aniline}

Djamel, D.; Tahar, D.; Djahida, H.; Hanane, H.; Salah, C.

doi:10.1107/S1600536811016011

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1318

doi:10.1107/S1600536811016011

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4,4′-Methylenebis{N-[(E)-quinolin-2-ylmethylidene]aniline}

Daoud Djamel,^a ^* Douadi Tahar,^a Haffar Djahida,^a Hammani Hanane ^a and Chafaa Salah ^a

^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

(Received 25 March 2011; accepted 27 April 2011; online 7 May 2011)

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

C₃₃H₂₄N₄
M_r = 476.56
Triclinic, P 1
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[F² > 2σ(F²)] = 0.035
wR(F²) = 0.087
S = 1.10
2707 reflections
335 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016011/fy2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016011/fy2004Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016011/fy2004Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2002); cell refinement: 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).

Figures top

Fig. 1. The title molecule with displacement ellipsoids for non–H atoms drawn at the 50% probability level.

4,4'-Methylenebis{N-[(E)-quinolin-2-ylmethylidene]aniline} top

Crystal data top

C₃₃H₂₄N₄	F(000) = 250
M_r = 476.56	D_x = 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

Data collection top

Bruker APEXII diffractometer	2415 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	R_int = 0.025
Graphite monochromator	θ_max = 27.4°, θ_min = 3.5°
CCD rotation images, thick slices scans	h = −5→5
9094 measured reflections	k = −7→7
2707 independent reflections	l = −28→28

Refinement top

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(F_o²) + (0.0373P)² + 0.1098P] where P = (F_o² + 2F_c²)/3
2707 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 0.21 e Å⁻³
3 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₃₃H₂₄N₄	γ = 78.044 (2)°
M_r = 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)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.035	3 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.10	Δρ_max = 0.21 e Å⁻³
2707 reflections	Δρ_min = −0.16 e Å⁻³
335 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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.

References

Ahamad, I., Prasad, R. & Quraishi, M. A. (2010). Corros. Sci. 52, 933–942. Web of Science CrossRef CAS Google Scholar
Bruker (2002). APEX2, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Y., Zhao, Y., Lu, C., Tzeng, C. & Wang, J. (2006). Bioorg. Med. Chem. 14, 4373–4378. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Ghames, A., Douadi, T., Haffar, D., Chafaa, S., Allain, M., Khan, M. A. & Bouet, G. M. (2006). Polyhedron, 25, 3201–3208. Web of Science CSD CrossRef CAS Google Scholar
Gilmartin, M. A. T. & Hart, J. P. (1995). Analyst, 120, 1029–1045. CrossRef CAS PubMed Web of Science Google Scholar
Girija, C. R., Begum, N. S., Sridhar, M. A., Lokanath, N. K. & Prasad, J. S. (2004). Acta Cryst. E60, o586–o588. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gómez-Barrio, A., Montero-Pereira, D., Nogal-Ruiz, J. J., Escario, J. A., Muelas-Serrano, S., Kouznetsov, V. V., Vargas Mendez, L. Y., Urbina González, J. M. & Ochoa, C. (2006). Acta Parasitol. 51, 73–78. Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o3087. Web of Science CSD CrossRef IUCr Journals Google Scholar
Issaadi, S., Haffar, D., Douadi, T., Chafaa, S., Séraphin, D., Khan, M. A. & Bouet, G. M. (2005). Synth. React. Inorg. Met. Org. Nano-Met. Chem. 35, 875–882. CrossRef CAS Google Scholar
Izatt, R. M., Pawlak, M. K. & Bardshaw, I. S. (1995). Chem. Rev. 95, 2529–2586. CrossRef CAS Web of Science Google Scholar
Jain, M., Khan, S., Tekwani, B., Jacob, M., Singh, S., Singh, B. & Jain, R. (2005). Bioorg. Med. Chem. 13, 4458–4466. Web of Science CrossRef PubMed CAS Google Scholar
Kaabi, I., Haffar, D., Douadi, T., Chafaa, S., Allain, M., Khan, M. A. & Bouet, G. M. (2007). Transition Met. Chem. 32, 666–673. CSD CrossRef CAS Google Scholar
Kalcher, K., Kauffman, J. M., Wank, J., Vaneare, I. S., Vitras, K., Neuhal, C. & Yang, Z. (1995). Electroanalysis, 7, 5–22. CrossRef CAS Web of Science Google Scholar
Kidwai, M., Bhushan, K., Sapra, P., Saxena, R. & Gupta, R. (2000). Bioorg. Med. Chem. 8, 69–72. Web of Science CrossRef PubMed CAS Google Scholar
Musiol, R., Jampilek, J., Buchta, V., Silva, L., Niebala, H., Podeszwa, B., Palka, A., Majerz-Maniecka, K., Oleksyn, B. & Polanski, J. (2006). Bioorg. Med. Chem. 14, 3592–3598. Web of Science CrossRef PubMed CAS Google Scholar
Negm, N. A., Elkholy, Y. M., Zahran, M. K. & Tawfik, S. M. (2010). Corros. Sci. 52, 3523–3536. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Souza, M. V. N. (2005). Mini Rev. Med. Chem. 5, 1009–1017. Web of Science PubMed Google Scholar
Vinsova, J., Imramovsky, A., Jampilek, J., Monreal-Ferriz, J. & Dolezal, M. (2008). Anti-Infect. Agent. Med. Chem. 7, 12–31. CrossRef CAS Google Scholar