4,4'-Oxybis{N-[(E)-quinolin-2-yl-methyl-idene]aniline}.

The title Schiff base compound, C(32)H(22)N(4)O, was prepared by a reaction of 4,4'-diamino-diphenyl ether and 2-quinoline-carboxaldehyde. The mol-ecule consists of two 4-{N-[(E)-quinolin-2-yl-methyl-idene]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. Inter-molecular 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 = 478.54

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.150

S = 1.1

5473 reflections

334 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.30 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/S1600536811012955/xu5181sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C32H22N4O	Dx = 1.338 Mg m−3
Mr = 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

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

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(Fo2) + (0.0834P)2 + 0.4121P] where P = (Fo2 + 2Fc2)/3
5473 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.30 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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .