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

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

doi:10.1107/S1600536811012955

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1119-o1120

doi:10.1107/S1600536811012955

Open

access

4,4′-Oxybis{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 24 March 2011; accepted 6 April 2011; online 13 April 2011)

The title Schiff base compound, C₃₂H₂₂N₄O, was prepared by a reaction of 4,4′-diaminodiphenyl ether and 2-quinolinecarboxaldehyde. The molecule consists of two 4-{N-[(E)-quinolin-2-ylmethylidene]amino}phenyl units linked by an oxygen bridge. The dihedral angles between two benzene rings and between the two quinoline ring systems are 53.81 (7) and 42.56 (4)°, respectively. Intermolecular C—H⋯N hydrogen bonding is present in the crystal structure.

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 applications of Schiff base compounds formed by aromatic diamine and a quinolinealdehyde, see: Izatt et al. (1995 ); Kalcher et al. (1995 ); Gilmartin & Hart (1995 ); 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

C₃₂H₂₂N₄O
M_r = 478.54
Monoclinic, P 2₁ /n
a = 17.4533 (7) Å
b = 5.0836 (2) Å
c = 26.817 (1) Å
β = 92.839 (1)°
V = 2376.43 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.05 × 0.05 mm

Data collection

Bruker APEXII diffractometer
20425 measured reflections
5473 independent reflections
4143 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.150
S = 1.1
5473 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯N3ⁱ	0.93	2.57	3.434 (2)	156
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811012955/xu5181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012955/xu5181Isup2.hkl

checkCIF report

Comment top

Quinolines and their derivatives are often used for designing of many synthetic compounds with diverse pharmacological and medicinal proprieties. Literature survey reveled that substituted quinolines possess diverse chemotherapeutic activities such as 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 in water treatment, they have a great capacity for complexation of transition metals (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) reveal their importance.

The compound, C₃₂H₂₂N₄O prepared is a condensation product of quinolinealdehyde with bifunctional aromatic diamine as shown in Fig (1). All the molecule is found in a single asymmetric unit although, the two 4-{N-[(E) -quinolin-2-ylmethylidene] amino}phenyl moieties are related by a pseudo mirror plane. A dihedral angle of 53.15° is found between the planes defined as (O(1)—C(17)—C(18)—C(19)—C(20)—C(21)—C(22) and O(1)—C(11)—C(12)—C(13)—C(14)—C(15)—C(16). Whereas the dihedral angle between each imine phenyl plane and the attached quinolinecarboxy plane are 8.33° for C(10)—N(2)—C(11) and 17.74° for C(25)—N(1)—C(20). The bond lengths N(2)—C(10), N(2)—C(11), O(1)—C(14).. and bond angles C(10)—N(2)—C(11), C(16)—C(11)—N(2), C(9)—N(3)—C(1), N(3)—C(1)—C(2) of one 4-{N-[(E) -quinolin-2-ylmethylidene] amino}phenyl moiety are similar the corresponding ones N(1)—C(25), N(1)—C20), O(1)—C(17).. and C(25)—N(1)—C(20), C(19)—C(20)—N(1), C(26)—N(4)—C(30, N(4)—C(30)—C(31)..of the second 4-{N-[(E) -quinolin-2-ylmethylidene] amino}phenyl. The bond distances shown in table 3 indicate that the N(1)—C(25) imine (C=N) bond length of 1.268 (17) A agree with similar double bond usually observed in related compounds (Girija et al., 2004) but much shorter than single C—N 1.4175 (16) A of N(1)—C(20) (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 applications of Schiff base compounds formed by aromatic diamine and a quinolinealdehyde, see: Izatt et al. (1995); Kalcher et al. (1995); Gilmartin & Hart (1995); 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 in proper literature (Issaadi et al., 2005; Ghames et al., 2006; Kaabi et al., 2007). by reacting the mixture of 4,4'-diaminodiphenyl ether (0.4 mg, 0.002 mol) and 2-quinolinecarboxaldehyde (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.
	Fig. 2. Packing of the molecules along the b–axis.

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

Crystal data top

C₃₂H₂₂N₄O	D_x = 1.338 Mg m⁻³
M_r = 478.54	Melting point: 491 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.4533 (7) Å	Cell parameters from 5947 reflections
b = 5.0836 (2) Å	θ = 2.3–27.4°
c = 26.817 (1) Å	µ = 0.08 mm⁻¹
β = 92.839 (1)°	T = 293 K
V = 2376.43 (16) Å³	Needle, colourless
Z = 4	0.25 × 0.05 × 0.05 mm
F(000) = 1000

Data collection top

Bruker APEXII diffractometer	4143 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	R_int = 0.035
Graphite monochromator	θ_max = 27.5°, θ_min = 1.4°
CCD rotation images, thick slices scans	h = −22→22
20425 measured reflections	k = −6→6
5473 independent reflections	l = −34→34

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.1	w = 1/[σ²(F_o²) + (0.0834P)² + 0.4121P] where P = (F_o² + 2F_c²)/3
5473 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₃₂H₂₂N₄O	V = 2376.43 (16) Å³
M_r = 478.54	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 17.4533 (7) Å	µ = 0.08 mm⁻¹
b = 5.0836 (2) Å	T = 293 K
c = 26.817 (1) Å	0.25 × 0.05 × 0.05 mm
β = 92.839 (1)°

Data collection top

Bruker APEXII diffractometer	4143 reflections with I > 2σ(I)
20425 measured reflections	R_int = 0.035
5473 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.1	Δρ_max = 0.31 e Å⁻³
5473 reflections	Δρ_min = −0.30 e Å⁻³
334 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	0.44063 (7)	0.2230 (2)	0.11249 (4)	0.0237 (3)
N4	0.57723 (7)	−0.2658 (2)	0.14573 (4)	0.0227 (3)
O1	0.32016 (6)	0.7878 (2)	−0.05150 (4)	0.0302 (3)
C25	0.49844 (8)	0.0726 (3)	0.11071 (5)	0.0239 (3)
H25	0.5257	0.0662	0.0818	0.029*
N3	−0.04347 (7)	1.8407 (3)	−0.14217 (5)	0.0282 (3)
C26	0.52279 (8)	−0.0916 (3)	0.15378 (5)	0.0221 (3)
N2	0.04205 (8)	1.3301 (3)	−0.06988 (5)	0.0294 (3)
C30	0.60189 (8)	−0.4232 (3)	0.18480 (5)	0.0220 (3)
C14	0.25109 (8)	0.9214 (3)	−0.05263 (5)	0.0242 (3)
C22	0.39182 (8)	0.4332 (3)	−0.01897 (5)	0.0250 (3)
H22	0.3994	0.382	−0.0517	0.03*
C21	0.42483 (8)	0.2911 (3)	0.02053 (5)	0.0250 (3)
H21	0.4545	0.144	0.0143	0.03*
C18	0.33675 (9)	0.7328 (3)	0.03893 (6)	0.0259 (3)
H18	0.3079	0.8823	0.045	0.031*
C11	0.11440 (9)	1.2017 (3)	−0.06541 (5)	0.0258 (3)
C9	−0.04232 (9)	1.6533 (3)	−0.10785 (5)	0.0263 (3)
C13	0.24528 (9)	1.1256 (3)	−0.08705 (6)	0.0271 (3)
H13	0.2869	1.1686	−0.1058	0.033*
C6	−0.18146 (9)	1.8825 (3)	−0.13310 (6)	0.0269 (3)
C12	0.17775 (9)	1.2639 (3)	−0.09323 (6)	0.0304 (4)
H12	0.1741	1.4008	−0.1162	0.036*
C20	0.41394 (8)	0.3668 (3)	0.06980 (5)	0.0216 (3)
C16	0.12138 (9)	0.9950 (3)	−0.03153 (6)	0.0281 (3)
H16	0.0798	0.9508	−0.0128	0.034*
C17	0.34752 (8)	0.6517 (3)	−0.00961 (5)	0.0234 (3)
C29	0.57228 (8)	−0.4008 (3)	0.23301 (5)	0.0235 (3)
C10	0.03217 (9)	1.5231 (3)	−0.09934 (6)	0.0298 (3)
H10	0.0738	1.5847	−0.1163	0.036*
C31	0.65914 (9)	−0.6133 (3)	0.17642 (6)	0.0264 (3)
H31	0.6786	−0.6303	0.1449	0.032*
C19	0.36957 (8)	0.5879 (3)	0.07820 (5)	0.0247 (3)
H19	0.3618	0.6396	0.1108	0.03*
C34	0.60200 (9)	−0.5671 (3)	0.27190 (6)	0.0278 (3)
H34	0.5836	−0.5531	0.3038	0.033*
C28	0.51373 (9)	−0.2130 (3)	0.23956 (6)	0.0269 (3)
H28	0.4925	−0.1939	0.2705	0.032*
C1	−0.11244 (9)	1.9575 (3)	−0.15479 (5)	0.0260 (3)
C33	0.65745 (9)	−0.7475 (3)	0.26262 (6)	0.0311 (4)
H33	0.6767	−0.8554	0.2883	0.037*
C27	0.48872 (9)	−0.0606 (3)	0.20035 (5)	0.0258 (3)
H27	0.4499	0.062	0.204	0.031*
C15	0.18910 (9)	0.8532 (3)	−0.02517 (6)	0.0290 (3)
H15	0.1928	0.7139	−0.0027	0.035*
C5	−0.25113 (9)	2.0034 (3)	−0.15027 (6)	0.0315 (4)
H5	−0.2971	1.9519	−0.1371	0.038*
C32	0.68574 (9)	−0.7717 (3)	0.21458 (6)	0.0300 (4)
H32	0.723	−0.8972	0.2088	0.036*
C7	−0.17651 (9)	1.6876 (3)	−0.09530 (6)	0.0345 (4)
H7	−0.2201	1.6375	−0.0792	0.041*
C8	−0.10793 (10)	1.5743 (3)	−0.08275 (6)	0.0337 (4)
H8	−0.1041	1.4464	−0.058	0.04*
C4	−0.25106 (10)	2.1942 (4)	−0.18585 (6)	0.0369 (4)
H4	−0.297	2.2737	−0.1966	0.044*
C2	−0.11438 (10)	2.1559 (3)	−0.19178 (6)	0.0364 (4)
H2	−0.0692	2.207	−0.2061	0.044*
C3	−0.18194 (11)	2.2725 (4)	−0.20663 (6)	0.0400 (4)
H3	−0.1825	2.4047	−0.2306	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0243 (6)	0.0236 (6)	0.0232 (6)	0.0024 (5)	−0.0005 (5)	0.0004 (5)
N4	0.0221 (6)	0.0231 (6)	0.0229 (6)	0.0018 (5)	0.0005 (5)	0.0003 (5)
O1	0.0309 (6)	0.0349 (6)	0.0252 (5)	0.0122 (5)	0.0048 (4)	0.0085 (5)
C25	0.0242 (7)	0.0250 (7)	0.0226 (7)	0.0017 (6)	0.0025 (6)	0.0008 (6)
N3	0.0258 (7)	0.0310 (7)	0.0280 (7)	0.0043 (5)	0.0030 (5)	0.0047 (5)
C26	0.0203 (7)	0.0224 (7)	0.0234 (7)	−0.0010 (6)	0.0000 (5)	0.0003 (6)
N2	0.0285 (7)	0.0292 (7)	0.0304 (7)	0.0052 (6)	0.0017 (5)	0.0042 (6)
C30	0.0205 (7)	0.0206 (7)	0.0247 (7)	−0.0018 (6)	−0.0021 (5)	0.0005 (5)
C14	0.0255 (7)	0.0241 (7)	0.0228 (7)	0.0043 (6)	−0.0008 (6)	−0.0010 (6)
C22	0.0237 (7)	0.0290 (8)	0.0224 (7)	0.0025 (6)	0.0027 (6)	−0.0012 (6)
C21	0.0235 (7)	0.0236 (7)	0.0279 (7)	0.0065 (6)	0.0022 (6)	−0.0018 (6)
C18	0.0273 (8)	0.0205 (7)	0.0299 (8)	0.0053 (6)	0.0031 (6)	−0.0003 (6)
C11	0.0259 (8)	0.0257 (7)	0.0255 (7)	0.0023 (6)	−0.0012 (6)	0.0002 (6)
C9	0.0282 (8)	0.0269 (8)	0.0239 (7)	0.0035 (6)	0.0017 (6)	0.0011 (6)
C13	0.0269 (8)	0.0304 (8)	0.0243 (7)	0.0027 (6)	0.0038 (6)	0.0042 (6)
C6	0.0275 (8)	0.0260 (7)	0.0273 (7)	0.0022 (6)	0.0017 (6)	−0.0055 (6)
C12	0.0334 (9)	0.0290 (8)	0.0288 (8)	0.0052 (7)	0.0020 (6)	0.0085 (6)
C20	0.0195 (7)	0.0211 (7)	0.0242 (7)	0.0004 (6)	0.0009 (5)	0.0016 (5)
C16	0.0270 (8)	0.0285 (8)	0.0289 (8)	0.0007 (6)	0.0032 (6)	0.0040 (6)
C17	0.0216 (7)	0.0238 (7)	0.0248 (7)	0.0011 (6)	0.0007 (5)	0.0051 (6)
C29	0.0234 (7)	0.0222 (7)	0.0246 (7)	−0.0041 (6)	−0.0015 (6)	0.0002 (6)
C10	0.0263 (8)	0.0336 (8)	0.0297 (8)	0.0025 (7)	0.0027 (6)	0.0050 (7)
C31	0.0260 (7)	0.0262 (7)	0.0271 (7)	0.0012 (6)	0.0014 (6)	−0.0007 (6)
C19	0.0262 (7)	0.0245 (7)	0.0235 (7)	0.0018 (6)	0.0024 (6)	−0.0025 (6)
C34	0.0302 (8)	0.0290 (8)	0.0237 (7)	−0.0046 (6)	−0.0030 (6)	0.0028 (6)
C28	0.0291 (8)	0.0295 (8)	0.0223 (7)	0.0003 (6)	0.0043 (6)	−0.0020 (6)
C1	0.0280 (8)	0.0276 (7)	0.0226 (7)	0.0038 (6)	0.0015 (6)	−0.0011 (6)
C33	0.0318 (8)	0.0283 (8)	0.0322 (8)	−0.0019 (7)	−0.0090 (6)	0.0072 (6)
C27	0.0246 (7)	0.0260 (7)	0.0269 (7)	0.0036 (6)	0.0025 (6)	−0.0019 (6)
C15	0.0299 (8)	0.0271 (8)	0.0301 (8)	0.0029 (7)	0.0019 (6)	0.0092 (6)
C5	0.0255 (8)	0.0334 (8)	0.0359 (8)	0.0066 (7)	0.0033 (6)	−0.0085 (7)
C32	0.0261 (8)	0.0252 (8)	0.0380 (9)	0.0036 (6)	−0.0047 (7)	0.0002 (6)
C7	0.0284 (8)	0.0351 (9)	0.0410 (9)	0.0015 (7)	0.0128 (7)	0.0036 (7)
C8	0.0348 (9)	0.0325 (8)	0.0345 (8)	0.0055 (7)	0.0088 (7)	0.0111 (7)
C4	0.0349 (9)	0.0431 (10)	0.0317 (8)	0.0172 (8)	−0.0071 (7)	−0.0092 (7)
C2	0.0368 (9)	0.0402 (9)	0.0328 (8)	0.0088 (8)	0.0081 (7)	0.0092 (7)
C3	0.0486 (11)	0.0412 (10)	0.0302 (8)	0.0152 (8)	0.0012 (7)	0.0089 (7)

Geometric parameters (Å, º) top

N1—C25	1.2686 (18)	C6—C7	1.417 (2)
N1—C20	1.4177 (18)	C6—C5	1.419 (2)
N4—C26	1.3241 (18)	C12—H12	0.93
N4—C30	1.3706 (18)	C20—C19	1.389 (2)
O1—C14	1.3828 (18)	C16—C15	1.388 (2)
O1—C17	1.3841 (17)	C16—H16	0.93
C25—C26	1.471 (2)	C29—C28	1.416 (2)
C25—H25	0.93	C29—C34	1.421 (2)
N3—C9	1.3240 (19)	C10—H10	0.93
N3—C1	1.3697 (19)	C31—C32	1.365 (2)
C26—C27	1.418 (2)	C31—H31	0.93
N2—C10	1.266 (2)	C19—H19	0.93
N2—C11	1.4213 (19)	C34—C33	1.365 (2)
C30—C31	1.416 (2)	C34—H34	0.93
C30—C29	1.420 (2)	C28—C27	1.361 (2)
C14—C15	1.383 (2)	C28—H28	0.93
C14—C13	1.389 (2)	C1—C2	1.414 (2)
C22—C17	1.384 (2)	C33—C32	1.408 (2)
C22—C21	1.384 (2)	C33—H33	0.93
C22—H22	0.93	C27—H27	0.93
C21—C20	1.398 (2)	C15—H15	0.93
C21—H21	0.93	C5—C4	1.361 (2)
C18—C19	1.386 (2)	C5—H5	0.93
C18—C17	1.387 (2)	C32—H32	0.93
C18—H18	0.93	C7—C8	1.355 (2)
C11—C16	1.391 (2)	C7—H7	0.93
C11—C12	1.400 (2)	C8—H8	0.93
C9—C8	1.415 (2)	C4—C3	1.411 (3)
C9—C10	1.467 (2)	C4—H4	0.93
C13—C12	1.375 (2)	C2—C3	1.362 (2)
C13—H13	0.93	C2—H2	0.93
C6—C1	1.416 (2)	C3—H3	0.93

C25—N1—C20	120.70 (13)	C28—C29—C34	123.35 (14)
C26—N4—C30	117.80 (12)	C30—C29—C34	118.97 (14)
C14—O1—C17	121.91 (11)	N2—C10—C9	122.63 (15)
N1—C25—C26	120.80 (13)	N2—C10—H10	118.7
N1—C25—H25	119.6	C9—C10—H10	118.7
C26—C25—H25	119.6	C32—C31—C30	120.01 (14)
C9—N3—C1	117.82 (13)	C32—C31—H31	120
N4—C26—C27	123.60 (13)	C30—C31—H31	120
N4—C26—C25	115.68 (13)	C18—C19—C20	121.29 (13)
C27—C26—C25	120.72 (13)	C18—C19—H19	119.4
C10—N2—C11	120.10 (14)	C20—C19—H19	119.4
N4—C30—C31	118.33 (13)	C33—C34—C29	120.17 (14)
N4—C30—C29	122.30 (13)	C33—C34—H34	119.9
C31—C30—C29	119.37 (13)	C29—C34—H34	119.9
C15—C14—O1	124.71 (13)	C27—C28—C29	119.59 (14)
C15—C14—C13	120.53 (14)	C27—C28—H28	120.2
O1—C14—C13	114.60 (13)	C29—C28—H28	120.2
C17—C22—C21	119.69 (13)	N3—C1—C2	118.23 (14)
C17—C22—H22	120.2	N3—C1—C6	122.47 (14)
C21—C22—H22	120.2	C2—C1—C6	119.28 (14)
C22—C21—C20	120.59 (13)	C34—C33—C32	120.64 (14)
C22—C21—H21	119.7	C34—C33—H33	119.7
C20—C21—H21	119.7	C32—C33—H33	119.7
C19—C18—C17	119.01 (13)	C28—C27—C26	119.00 (14)
C19—C18—H18	120.5	C28—C27—H27	120.5
C17—C18—H18	120.5	C26—C27—H27	120.5
C16—C11—C12	118.21 (14)	C14—C15—C16	119.23 (14)
C16—C11—N2	116.80 (14)	C14—C15—H15	120.4
C12—C11—N2	124.97 (14)	C16—C15—H15	120.4
N3—C9—C8	123.37 (14)	C4—C5—C6	120.38 (16)
N3—C9—C10	114.56 (14)	C4—C5—H5	119.8
C8—C9—C10	122.00 (14)	C6—C5—H5	119.8
C12—C13—C14	119.72 (14)	C31—C32—C33	120.83 (15)
C12—C13—H13	120.1	C31—C32—H32	119.6
C14—C13—H13	120.1	C33—C32—H32	119.6
C1—C6—C7	117.34 (14)	C8—C7—C6	119.76 (15)
C1—C6—C5	118.88 (14)	C8—C7—H7	120.1
C7—C6—C5	123.78 (15)	C6—C7—H7	120.1
C13—C12—C11	121.00 (14)	C7—C8—C9	119.14 (15)
C13—C12—H12	119.5	C7—C8—H8	120.4
C11—C12—H12	119.5	C9—C8—H8	120.4
C19—C20—C21	118.61 (13)	C5—C4—C3	120.57 (15)
C19—C20—N1	116.72 (13)	C5—C4—H4	119.7
C21—C20—N1	124.52 (13)	C3—C4—H4	119.7
C15—C16—C11	121.29 (14)	C3—C2—C1	120.41 (16)
C15—C16—H16	119.4	C3—C2—H2	119.8
C11—C16—H16	119.4	C1—C2—H2	119.8
C22—C17—O1	115.31 (13)	C2—C3—C4	120.44 (16)
C22—C17—C18	120.79 (13)	C2—C3—H3	119.8
O1—C17—C18	123.77 (13)	C4—C3—H3	119.8
C28—C29—C30	117.68 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N3ⁱ	0.93	2.57	3.434 (2)	156

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₂N₄O
M_r	478.54
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	17.4533 (7), 5.0836 (2), 26.817 (1)
β (°)	92.839 (1)
V (Å³)	2376.43 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.05 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20425, 5473, 4143
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.150, 1.1
No. of reflections	5473
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.30

Computer programs: APEX2 (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28···N3ⁱ	0.93	2.57	3.434 (2)	156

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Acknowledgements

The authors thank 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 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., uelas-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. & Boue, 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-Infec. Agents Med. Chem. 7, 12–31. CrossRef CAS Google Scholar