Bis[4-(2-benzyl-idenepropyl-idene-amino)phen-yl] ether.

The title compound, C(32)H(28)N(2)O, is a flexible Schiff base displaying a trans configuration across the C=N double bond. It was prepared in high yield by condensation of α-methyl-cinnamaldehyde and bis-(4-amino-phen-yl) ether in methanol at room temperature. The sample, with pseudo-ortho-rhom-bic cell parameters, exhibited merohedral twinning by rotation 180° around a*, with a refined twin domain fraction of 0.722 (1). The elongated shape of the elementary cell corresponds to the shape and direction of the mol-ecules. The dihedral angle between the O-linked aromatic rings is 57.86 (8)°.

Related literature

For the synthesis of the title compound, see: Khalaji & Ng (2008 ▶). For related structures, see: Hu et al. (2008 ▶); Xu et al. (2008 ▶). For background to transition metal complexes, see: Laye (2007 ▶); Huang et al. (2005 ▶); Chu & Huang (2007 ▶).

Experimental

Crystal data

C32H28N2O

M = 456.6

Monoclinic,

a = 7.4737 (3) Å

b = 55.929 (3) Å

c = 6.0275 (3) Å

β = 90.022 (4)°

V = 2519.5 (2) Å3

Z = 4

Cu Kα radiation

μ = 0.56 mm−1

T = 295 K

0.51 × 0.38 × 0.02 mm

Data collection

Oxford Diffraction Gemini diffractometer with Atlas CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.682, T max = 0.99

15440 measured reflections

3838 independent reflections

3428 reflections with I > 3σ(I)

R int = 0.016

θmax = 61.4°

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.120

S = 2.32

3838 reflections

317 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis n class="Disease">RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005005/bt2870sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005005/bt2870Isup2.hkl

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

C32H28N2O	F(000) = 968
Mr = 456.6	Dx = 1.203 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 9034 reflections
a = 7.4737 (3) Å	θ = 3.2–61.2°
b = 55.929 (3) Å	µ = 0.56 mm−1
c = 6.0275 (3) Å	T = 295 K
β = 90.022 (4)°	Plate, yellow
V = 2519.5 (2) Å3	0.51 × 0.38 × 0.02 mm
Z = 4

Oxford Diffraction Gemini diffractometer with Atlas CCD detector	3838 independent reflections
Radiation source: X-ray tube	3428 reflections with I > 3σ(I)
mirrors	Rint = 0.016
Detector resolution: 20.7567 pixels mm-1	θmax = 61.4°, θmin = 3.2°
Rotation method data acquisition using ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −62→62
Tmin = 0.682, Tmax = 0.99	l = −6→6
15440 measured reflections

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.120	H-atom parameters constrained
S = 2.32	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
3838 reflections	(Δ/σ)max = 0.001
317 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3
112 constraints

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
O1	0.41159 (19)	0.25020 (2)	1.1527 (2)	0.0638 (4)
N1	0.4123 (2)	0.33936 (3)	0.7401 (3)	0.0617 (5)
N2	0.4264 (2)	0.16126 (3)	0.7377 (3)	0.0623 (5)
C1	0.4131 (2)	0.27183 (3)	1.0403 (3)	0.0548 (5)
C2	0.4984 (2)	0.29047 (3)	1.1464 (3)	0.0613 (6)
C3	0.4970 (2)	0.31299 (3)	1.0534 (3)	0.0635 (6)
C4	0.4118 (2)	0.31709 (3)	0.8503 (3)	0.0568 (5)
C5	0.3295 (2)	0.29795 (3)	0.7467 (3)	0.0601 (6)
C6	0.3268 (2)	0.27553 (3)	0.8402 (3)	0.0616 (6)
C7	0.4096 (2)	0.35875 (3)	0.8483 (3)	0.0636 (6)
C8	0.4215 (2)	0.38208 (3)	0.7420 (3)	0.0600 (6)
C9	0.4227 (2)	0.40156 (3)	0.8727 (3)	0.0639 (6)
C10	0.4388 (2)	0.42689 (3)	0.8176 (3)	0.0602 (6)
C11	0.5287 (3)	0.43555 (4)	0.6318 (4)	0.0723 (7)
C12	0.5396 (3)	0.45964 (4)	0.5896 (4)	0.0859 (9)
C13	0.4641 (3)	0.47591 (4)	0.7318 (4)	0.0875 (9)
C14	0.3778 (3)	0.46796 (4)	0.9185 (4)	0.0842 (8)
C15	0.3661 (3)	0.44386 (4)	0.9620 (4)	0.0712 (7)
C16	0.4273 (3)	0.38214 (4)	0.4939 (3)	0.0780 (8)
C17	0.4135 (2)	0.22865 (3)	1.0395 (3)	0.0555 (5)
C18	0.3308 (2)	0.20971 (3)	1.1439 (3)	0.0613 (6)
C19	0.3356 (2)	0.18727 (3)	1.0517 (3)	0.0628 (6)
C20	0.4223 (2)	0.18353 (3)	0.8484 (3)	0.0574 (5)
C21	0.5012 (2)	0.20285 (3)	0.7441 (3)	0.0606 (6)
C22	0.5005 (2)	0.22525 (3)	0.8389 (3)	0.0612 (6)
C23	0.4375 (2)	0.14192 (4)	0.8456 (3)	0.0648 (6)
C24	0.4369 (2)	0.11855 (3)	0.7384 (3)	0.0609 (6)
C25	0.4481 (2)	0.09907 (3)	0.8688 (3)	0.0644 (6)
C26	0.4490 (2)	0.07366 (3)	0.8136 (3)	0.0612 (6)
C27	0.3678 (3)	0.06393 (4)	0.6255 (4)	0.0716 (7)
C28	0.3726 (3)	0.03972 (4)	0.5842 (4)	0.0843 (8)
C29	0.4589 (3)	0.02459 (4)	0.7274 (4)	0.0854 (8)
C30	0.5381 (3)	0.03360 (4)	0.9145 (4)	0.0862 (9)
C31	0.5324 (3)	0.05778 (4)	0.9586 (4)	0.0741 (7)
C32	0.4306 (3)	0.11845 (4)	0.4907 (3)	0.0773 (8)
H2	0.558692	0.287765	1.284787	0.0735*
H3	0.555012	0.325979	1.128755	0.0762*
H5	0.272697	0.300391	0.605623	0.0721*
H6	0.265779	0.262608	0.76752	0.0739*
H11	0.584073	0.424477	0.531363	0.0868*
H12	0.600738	0.46515	0.459163	0.1031*
H13	0.471712	0.492723	0.700898	0.105*
H14	0.325198	0.479257	1.01914	0.1011*
H15	0.306821	0.438587	1.094548	0.0855*
H18	0.26953	0.212226	1.281899	0.0736*
H19	0.279415	0.174115	1.126614	0.0753*
H21	0.557768	0.200601	0.602612	0.0728*
H22	0.559553	0.238363	0.76685	0.0734*
H27	0.307393	0.074305	0.523036	0.0859*
H28	0.315201	0.033414	0.454239	0.1011*
H29	0.463802	0.00776	0.696717	0.1024*
H30	0.597998	0.023017	1.01551	0.1035*
H31	0.586783	0.063783	1.091686	0.0889*
H7	0.399203	0.358045	1.006914	0.0763*
H9	0.410947	0.398259	1.028338	0.0767*
H23	0.446597	0.142663	1.004279	0.0778*
H25	0.457048	0.102463	1.024492	0.0773*
H16a	0.359347	0.36888	0.438036	0.0936*
H16b	0.37714	0.396808	0.439336	0.0936*
H16c	0.549168	0.380782	0.445248	0.0936*
H32a	0.493257	0.132162	0.434681	0.0927*
H32b	0.486302	0.104148	0.435939	0.0927*
H32c	0.308313	0.118963	0.442292	0.0927*

	U11	U22	U33	U12	U13	U23
O1	0.0715 (8)	0.0641 (7)	0.0559 (7)	−0.0001 (5)	0.0032 (7)	0.0004 (6)
N1	0.0581 (8)	0.0672 (9)	0.0598 (9)	−0.0006 (6)	0.0011 (7)	0.0000 (7)
N2	0.0611 (8)	0.0675 (9)	0.0585 (9)	−0.0007 (7)	0.0045 (7)	0.0004 (7)
C1	0.0445 (8)	0.0641 (10)	0.0559 (9)	0.0018 (7)	0.0061 (7)	−0.0017 (8)
C2	0.0571 (9)	0.0713 (11)	0.0554 (9)	0.0006 (8)	−0.0064 (8)	−0.0025 (9)
C3	0.0600 (10)	0.0670 (11)	0.0634 (11)	−0.0034 (8)	−0.0054 (8)	−0.0080 (9)
C4	0.0503 (8)	0.0659 (10)	0.0543 (9)	0.0003 (7)	0.0039 (8)	−0.0023 (8)
C5	0.0541 (9)	0.0719 (11)	0.0543 (9)	0.0012 (7)	−0.0042 (8)	−0.0032 (8)
C6	0.0505 (8)	0.0688 (11)	0.0655 (11)	−0.0027 (7)	−0.0066 (8)	−0.0065 (9)
C7	0.0698 (11)	0.0701 (11)	0.0508 (9)	0.0010 (8)	0.0035 (9)	0.0014 (9)
C8	0.0553 (9)	0.0703 (11)	0.0543 (10)	0.0018 (8)	0.0024 (8)	0.0043 (8)
C9	0.0703 (11)	0.0720 (11)	0.0495 (9)	0.0028 (8)	0.0028 (8)	0.0042 (9)
C10	0.0555 (9)	0.0704 (11)	0.0547 (10)	0.0015 (8)	−0.0040 (8)	0.0020 (8)
C11	0.0742 (11)	0.0766 (13)	0.0662 (11)	0.0011 (9)	0.0119 (10)	0.0048 (10)
C12	0.0964 (15)	0.0807 (14)	0.0807 (15)	−0.0061 (11)	0.0132 (12)	0.0151 (11)
C13	0.0925 (15)	0.0701 (13)	0.1000 (17)	−0.0013 (11)	−0.0004 (14)	0.0106 (12)
C14	0.0870 (14)	0.0745 (13)	0.0912 (16)	0.0068 (10)	0.0064 (13)	−0.0108 (12)
C15	0.0702 (12)	0.0789 (13)	0.0645 (11)	−0.0009 (9)	0.0054 (9)	−0.0040 (9)
C16	0.0973 (16)	0.0812 (13)	0.0555 (11)	−0.0032 (11)	0.0008 (11)	0.0019 (9)
C17	0.0456 (8)	0.0639 (10)	0.0572 (9)	0.0009 (7)	−0.0010 (7)	0.0014 (8)
C18	0.0559 (9)	0.0714 (11)	0.0568 (10)	0.0012 (8)	0.0096 (8)	0.0040 (9)
C19	0.0580 (9)	0.0670 (11)	0.0634 (11)	−0.0028 (8)	0.0117 (8)	0.0062 (9)
C20	0.0493 (8)	0.0668 (10)	0.0562 (9)	0.0013 (7)	0.0027 (8)	0.0026 (8)
C21	0.0560 (9)	0.0718 (11)	0.0541 (9)	0.0001 (7)	0.0104 (8)	0.0029 (8)
C22	0.0539 (9)	0.0674 (11)	0.0623 (10)	−0.0032 (7)	0.0109 (8)	0.0061 (8)
C23	0.0715 (11)	0.0708 (11)	0.0522 (9)	0.0025 (8)	0.0015 (9)	−0.0015 (9)
C24	0.0593 (10)	0.0709 (11)	0.0524 (10)	0.0004 (8)	0.0033 (8)	−0.0021 (8)
C25	0.0706 (11)	0.0733 (11)	0.0493 (9)	−0.0008 (8)	0.0002 (8)	−0.0044 (9)
C26	0.0570 (9)	0.0723 (11)	0.0543 (10)	−0.0016 (8)	0.0022 (8)	−0.0002 (8)
C27	0.0707 (11)	0.0774 (12)	0.0667 (12)	−0.0016 (9)	−0.0099 (10)	−0.0022 (10)
C28	0.0925 (15)	0.0827 (14)	0.0776 (14)	−0.0149 (11)	−0.0013 (12)	−0.0131 (12)
C29	0.0934 (15)	0.0725 (13)	0.0901 (16)	−0.0043 (11)	0.0137 (13)	−0.0041 (12)
C30	0.0947 (15)	0.0747 (13)	0.0892 (16)	0.0011 (11)	−0.0021 (13)	0.0167 (12)
C31	0.0793 (13)	0.0799 (14)	0.0630 (11)	−0.0062 (10)	−0.0057 (10)	0.0078 (10)
C32	0.0954 (15)	0.0798 (13)	0.0567 (11)	−0.0036 (11)	0.0032 (11)	−0.0016 (9)

O1—C1	1.386 (2)	C16—H16a	0.96
O1—C17	1.385 (2)	C16—H16b	0.96
N1—C4	1.412 (2)	C16—H16c	0.96
N1—C7	1.266 (2)	C17—C18	1.378 (2)
N2—C20	1.414 (2)	C17—C22	1.386 (3)
N2—C23	1.264 (2)	C18—C19	1.373 (3)
C1—C2	1.379 (2)	C18—H18	0.96
C1—C6	1.384 (3)	C19—C20	1.402 (3)
C2—C3	1.379 (3)	C19—H19	0.96
C2—H2	0.96	C20—C21	1.383 (3)
C3—C4	1.398 (3)	C21—C22	1.377 (3)
C3—H3	0.96	C21—H21	0.96
C4—C5	1.384 (2)	C22—H22	0.96
C5—C6	1.375 (3)	C23—C24	1.458 (3)
C5—H5	0.96	C23—H23	0.96
C6—H6	0.96	C24—C25	1.346 (3)
C7—C8	1.456 (3)	C24—C32	1.494 (3)
C7—H7	0.96	C25—C26	1.459 (3)
C8—C9	1.345 (3)	C25—H25	0.96
C8—C16	1.496 (3)	C26—C27	1.396 (3)
C9—C10	1.460 (3)	C26—C31	1.393 (3)
C9—H9	0.96	C27—C28	1.377 (3)
C10—C11	1.393 (3)	C27—H27	0.96
C10—C15	1.398 (3)	C28—C29	1.370 (3)
C11—C12	1.374 (3)	C28—H28	0.96
C11—H11	0.96	C29—C30	1.370 (4)
C12—C13	1.372 (3)	C29—H29	0.96
C12—H12	0.96	C30—C31	1.379 (3)
C13—C14	1.372 (4)	C30—H30	0.96
C13—H13	0.96	C31—H31	0.96
C14—C15	1.376 (3)	C32—H32a	0.96
C14—H14	0.96	C32—H32b	0.96
C15—H15	0.96	C32—H32c	0.96
C1—O1—C17	121.25 (14)	H16b—C16—H16c	109.4707
C4—N1—C7	120.89 (16)	O1—C17—C18	116.07 (16)
C20—N2—C23	120.83 (16)	O1—C17—C22	123.64 (15)
O1—C1—C2	115.92 (15)	C18—C17—C22	120.20 (16)
O1—C1—C6	123.52 (15)	C17—C18—C19	120.40 (17)
C2—C1—C6	120.45 (16)	C17—C18—H18	119.7986
C1—C2—C3	119.92 (17)	C19—C18—H18	119.8003
C1—C2—H2	120.0388	C18—C19—C20	120.14 (16)
C3—C2—H2	120.0374	C18—C19—H19	119.9296
C2—C3—C4	120.58 (17)	C20—C19—H19	119.9325
C2—C3—H3	119.7093	N2—C20—C19	123.66 (15)
C4—C3—H3	119.7097	N2—C20—C21	117.67 (16)
N1—C4—C3	123.73 (15)	C19—C20—C21	118.60 (16)
N1—C4—C5	118.11 (16)	C20—C21—C22	121.35 (17)
C3—C4—C5	118.09 (16)	C20—C21—H21	119.326
C4—C5—C6	121.81 (17)	C22—C21—H21	119.3271
C4—C5—H5	119.0935	C17—C22—C21	119.28 (16)
C6—C5—H5	119.0919	C17—C22—H22	120.3631
C1—C6—C5	119.12 (16)	C20—C22—H22	149.7198
C1—C6—H6	120.4391	N2—C23—C24	122.61 (18)
C5—C6—H6	120.4404	N2—C23—H23	118.6934
N1—C7—C8	122.68 (17)	C24—C23—H23	118.6931
N1—C7—H7	118.6563	C23—C24—C25	117.85 (17)
C8—C7—H7	118.6616	C23—C24—C32	116.50 (16)
C7—C8—C9	117.94 (17)	C25—C24—C32	125.61 (17)
C7—C8—C16	116.35 (16)	C24—C25—C26	130.95 (17)
C9—C8—C16	125.70 (17)	C24—C25—H25	114.5252
C8—C9—C10	130.80 (17)	C26—C25—H25	114.5237
C8—C9—H9	114.598	C25—C26—C27	124.25 (17)
C10—C9—H9	114.6038	C25—C26—C31	118.67 (17)
C9—C10—C11	124.07 (17)	C27—C26—C31	117.06 (18)
C9—C10—C15	119.02 (17)	C26—C27—C28	121.3 (2)
C11—C10—C15	116.87 (18)	C26—C27—H27	119.375
C10—C11—C12	121.3 (2)	C28—C27—H27	119.3729
C10—C11—H11	119.3764	C27—C28—C29	120.4 (2)
C12—C11—H11	119.3736	C27—C28—H28	119.8062
C11—C12—C13	120.7 (2)	C29—C28—H28	119.8072
C11—C12—H12	119.6501	C28—C29—C30	119.7 (2)
C13—C12—H12	119.6503	C28—C29—H29	120.1738
C12—C13—C14	119.4 (2)	C30—C29—H29	120.1722
C12—C13—H13	120.2841	C29—C30—C31	120.4 (2)
C14—C13—H13	120.2831	C29—C30—H30	119.7998
C13—C14—C15	120.3 (2)	C31—C30—H30	119.7949
C13—C14—H14	119.8703	C26—C31—C30	121.2 (2)
C15—C14—H14	119.8702	C26—C31—H31	119.3916
C10—C15—C14	121.5 (2)	C30—C31—H31	119.3905
C10—C15—H15	119.2735	C24—C32—H32a	109.4703
C14—C15—H15	119.2764	C24—C32—H32b	109.4721
C8—C16—H16a	109.4718	C24—C32—H32c	109.4709
C8—C16—H16b	109.4708	H32a—C32—H32b	109.4716
C8—C16—H16c	109.4712	H32a—C32—H32c	109.4711
H16a—C16—H16b	109.4705	H32b—C32—H32c	109.4713
H16a—C16—H16c	109.4723
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
?—?···?	?	?	?	?