(E,E) N,N′ Bis(1 phenyl­ethyl­­idene)ethyl­enedi­amine

organic papers

Acta Cryst.(2006). E62, o1971–o1972 doi:10.1107/S1600536806013614 Bensonet al. _C

18H20N2

o1971

Acta Crystallographica Section E Structure Reports Online

ISSN 1600-5368

(

E

,

E

)-

N

,

N

_{-Bis(1-phenylethylidene)ethylenediamine}

Ronald E. Benson,aTapashi G. Roy,bBenu K. Dey,bKanak K. Baruab and Edward R. T. Tiekinkc*

a_{Rigaku Americas Corporation, 9009 New Trails}

Drive, The Woodlands, Texas 77381, USA,

b_{Department of Chemistry, University of}

Chit-tagong, Chittagong 4331, Bangladesh, and

c_{Department of Chemistry, The University of}

Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study T= 113 K

Mean(C–C) = 0.002 A˚ Rfactor = 0.043 wRfactor = 0.117

Data-to-parameter ratio = 18.1

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 13 April 2006 Accepted 15 April 2006

#2006 International Union of Crystallography All rights reserved

The essentially planar title compound, C18H20N2, is disposed

about a center of inversion located at the mid-point of the ethylene bond and features an E configuration about each C N bond.

Comment

The title compound, (I), was isolated in an attempt to prepare a macrocyclic ligand in connection with our ongoing interest in macrocyclic complexes of transition metals (e.g. Roy et al., 2006); see Experimental for details. This molecule was first reported by Ferguson & Goodwin (1949) and now attracts interest as a ligand for transition metals with biological activity, e.g. antibacterial (Patel et al., 2005). Compound (I) (Fig. 1 and Table 1) is centrosymmetric about the ethylene bridge and the configuration about the C N bond isE. The entire molecule is essentially planar as evidenced in the values of the N1—C1—C4—C5, C3—N1—C1—C4 and N1—C3— C3i—N1i torsion angles of 6.15 (14), 178.62 (9) and 179.98 (11)_{, respectively [symmetry code: (i) 1 x, 1 y,}

z]. The observed configuration found for (I) contrasts with that observed in the only known crystal structure containing (I), in which it functions as a chelating ligand to an Mo(CO)4

unit (Paz-Sandovalet al., 1995). While there are no significant –interactions in the crystal structure of (I), there are C— H interactions with the closest being 2.70 A˚ , occurring between C2/H2B and the ring centroid of (C4–C9)iiwith an angle at H of 141 _{[symmetry code: (ii) 1x, 1y, 1z].}

These interactions lead to the formation of columns comprising off-set molecules.

Experimental

Compound (I) was isolated during reactions designed to form a new macrocyclic ligand following literature precedents (e.g.Bembiet al., 1989; Roy et al., 2001; Gasperov et al., 2004). Thus, the reaction between acetophenone (excess), diaminoethane and HClO4 in

Crystal data

C18H20N2

Mr= 264.36

Monoclinic,P21=n

a= 5.4713 (7) A˚ b= 14.1328 (17) A˚ c= 9.7392 (13) A˚ = 105.7130 (5)

V= 724.94 (16) A˚3

Z= 2

Dx= 1.211 Mg m

3 MoKradiation = 0.07 mm1

T= 113 (2) K Prism, colorless 0.510.400.22 mm

Data collection

Rigaku R-AXIS SPIDER diffractometer !scans

Absorption correction: numerical (Katayama, 1986; Paturle & Coppens, 1988)

Tmin= 0.978,Tmax= 0.992

9051 measured reflections 1666 independent reflections 1617 reflections withI> 2(I) Rint= 0.034

max= 27.5

Refinement

Refinement onF2 R[F2_{> 2(F}2_{)] = 0.043}

wR(F2) = 0.117 S= 1.07 1666 reflections 92 parameters

H-atom parameters constrained

w= 1/[2 (Fo

2

) + (0.0589P)2 + 0.2225P]

whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001

max= 0.32 e A˚

3 min=0.15 e A˚

3

Table 1

Selected geometric parameters (A˚ ,_).

N1—C1 1.2772 (13)

N1—C3 1.4668 (13)

C1—C2 1.5120 (14)

C1—C4 1.4999 (14)

C1—N1—C3 119.82 (9)

N1—C1—C2 125.77 (9)

C2—C1—C4 117.18 (8)

N1—C3—C3i

108.95 (11)

Symmetry code: (i)xþ1;yþ1;z.

All H atoms were allowed to ride on their parent atoms at distances of 0.95 (aromatic H), 0.98 (methyl H) and 0.99 A˚ (methylene H), and withUiso(H) values of 1.2Ueq(parent atom) for

aromatic and methylene H atoms, and 1.5Ueq(parent atom) for

methyl H atoms.

Data collection:CrystalClear(Rigaku/MSC, 2005); cell refinement:

CrystalClear; data reduction:CrystalClear; program(s) used to solve structure:SIR92 (Altomareet al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:

ORTEPII (Johnson, 1976); software used to prepare material for publication:SHELXL97.

The authors are grateful to the University of Chittagong for providing a scholarship to KKB.

References

Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994).J. Appl. Cryst.27, 435.

Bembi, R., Sondhi, S. M., Singh, A. K., Jhanji, A. K., Roy, T. G., Lown, J. W. & Ball, R. G. (1989).Bull. Chem. Soc. Jpn,62, 3701–3705.

Ferguson, L. N. & Goodwin, T. C. (1949).J. Am. Chem. Soc.71, 633–637. Gasperov, V., Gloe, K., Lindoy, L. F. & Mahinai, M. S. (2004).Dalton Trans.

pp. 3829–3834.

Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Katayama, C. (1986).Acta Cryst.A42, 19–23.

Patel, N. H., Parekh, H. M. & Patel, M. N. (2005).Transition Met. Chem.30, 13–17.

Paturle, A. & Coppens, P. (1988).Acta Cryst.A44, 6–7.

Paz-Sandoval, M. A., Dominguez-Duran, M. E., Pazos-Mayen, C., Ariza-Castolo, A., de Jesus, R.-H. M. & Contreras, R. (1995).J. Organomet. Chem. 492, 1–9.

Rigaku/MSC (2005).CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.

Roy, T. G., Hazari, S. K. S., Dey, B. K., Miah, H. A. & Tiekink, E. R. T. (2001). Acta Cryst.E57, o524–o525.

Roy, T. G., Hazari, S. K. S., Dey, B. K., Sutradhar, R., Dey, L., Anowar, N. & Tiekink, E. R. T. (2006).J. Coord. Chem.59, 351–362.

Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany.

Figure 1

supporting information

sup-1 Acta Cryst. (2006). E62, o1971–o1972

supporting information

Acta Cryst. (2006). E62, o1971–o1972 [https://doi.org/10.1107/S1600536806013614]

(

E

,

E

)-

N

,

N

′

-Bis(1-phenylethylidene)ethylenediamine

Ronald E. Benson, Tapashi G. Roy, Benu K. Dey, Kanak K. Barua and Edward R. T. Tiekink

(E,E)—N,N′-Bis(1-phenylethylidene)ethylenediamine

Crystal data C18H20N2 Mr = 264.36 Monoclinic, P21/n Hall symbol: -P 2yn a = 5.4713 (7) Å b = 14.1328 (17) Å c = 9.7392 (13) Å β = 105.7130 (5)° V = 724.94 (16) Å3 Z = 2

F(000) = 284 Dx = 1.211 Mg m−3

Mo Kα radiation, λ = 0.71069 Å Cell parameters from 29 reflections θ = 3.6–27.5°

µ = 0.07 mm−1 T = 113 K Prism, colorless 0.51 × 0.40 × 0.22 mm

Data collection

Rigaku R-AXIS SPIDER diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

Absorption correction: numerical

(Katayama, 1986; Paturle & Coppens, 1988) Tmin = 0.978, Tmax = 0.992

9051 measured reflections 1666 independent reflections 1617 reflections with I > 2σ(I) Rint = 0.034

θmax = 27.5°, θmin = 2.6° h = −7→7

k = −18→18 l = −12→12

Refinement Refinement on F2 Least-squares matrix: full R[F2 _{> 2σ(F}2_{)] = 0.043} wR(F2_{) = 0.117} S = 1.07 1666 reflections 92 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained w = 1/[σ2_(F

o2) + (0.0589P)2 + 0.2225P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.32 e Å−3 Δρmin = −0.15 e Å−3

Special details

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq N1 0.46963 (17) 0.45029 (6) 0.17131 (9) 0.0209 (2) C1 0.34532 (19) 0.45979 (7) 0.26415 (10) 0.0180 (2) C2 0.1569 (2) 0.53757 (7) 0.26674 (11) 0.0226 (3) H2A 0.1540 0.5829 0.1902 0.034* H2B 0.2071 0.5701 0.3590 0.034* H2C −0.0126 0.5101 0.2527 0.034* C3 0.4324 (2) 0.51817 (8) 0.05352 (11) 0.0226 (3) H3A 0.5020 0.5806 0.0905 0.027* H3B 0.2489 0.5257 0.0066 0.027* C4 0.38798 (18) 0.38664 (7) 0.37980 (10) 0.0181 (2) C5 0.5753 (2) 0.31716 (7) 0.39142 (11) 0.0218 (2) H5 0.6782 0.3177 0.3270 0.026* C6 0.6125 (2) 0.24755 (8) 0.49584 (12) 0.0249 (3) H6 0.7413 0.2013 0.5028 0.030* C7 0.4617 (2) 0.24538 (8) 0.59016 (12) 0.0257 (3) H7 0.4855 0.1973 0.6607 0.031* C8 0.2767 (2) 0.31386 (9) 0.58056 (12) 0.0282 (3) H8 0.1740 0.3129 0.6451 0.034* C9 0.2405 (2) 0.38420 (8) 0.47661 (11) 0.0239 (3) H9 0.1139 0.4311 0.4715 0.029*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23 N1 0.0242 (5) 0.0214 (4) 0.0186 (4) −0.0016 (3) 0.0085 (3) 0.0007 (3) C1 0.0185 (5) 0.0188 (5) 0.0165 (5) −0.0027 (3) 0.0043 (4) −0.0019 (3) C2 0.0263 (5) 0.0231 (5) 0.0199 (5) 0.0040 (4) 0.0086 (4) 0.0027 (4) C3 0.0277 (5) 0.0222 (5) 0.0201 (5) 0.0001 (4) 0.0104 (4) 0.0020 (4) C4 0.0188 (5) 0.0188 (5) 0.0168 (5) −0.0020 (4) 0.0049 (4) −0.0013 (4) C5 0.0243 (5) 0.0220 (5) 0.0213 (5) 0.0010 (4) 0.0099 (4) −0.0014 (4) C6 0.0271 (6) 0.0211 (5) 0.0273 (5) 0.0044 (4) 0.0086 (4) 0.0006 (4) C7 0.0286 (6) 0.0240 (5) 0.0248 (5) 0.0006 (4) 0.0077 (4) 0.0075 (4) C8 0.0280 (6) 0.0332 (6) 0.0280 (6) 0.0038 (4) 0.0152 (4) 0.0086 (4) C9 0.0229 (5) 0.0267 (5) 0.0247 (5) 0.0057 (4) 0.0109 (4) 0.0051 (4)

Geometric parameters (Å, º)

supporting information

sup-3 Acta Cryst. (2006). E62, o1971–o1972

C1—C4 1.4999 (14) C6—C7 1.3915 (15) C2—H2A 0.9800 C6—H6 0.9500 C2—H2B 0.9800 C7—C8 1.3850 (16) C2—H2C 0.9800 C7—H7 0.9500 C3—C3i _{1.521 (2) C8—C9 1.3942 (15)} C3—H3A 0.9900 C8—H8 0.9500 C3—H3B 0.9900 C9—H9 0.9500 C4—C5 1.4016 (14)

C1—N1—C3 119.82 (9) C5—C4—C1 120.35 (9) N1—C1—C2 125.77 (9) C9—C4—C1 121.52 (9) N1—C1—C4 117.05 (9) C6—C5—C4 120.94 (9) C2—C1—C4 117.18 (8) C6—C5—H5 119.5 C1—C2—H2A 109.5 C4—C5—H5 119.5 C1—C2—H2B 109.5 C5—C6—C7 120.20 (10) H2A—C2—H2B 109.5 C5—C6—H6 119.9 C1—C2—H2C 109.5 C7—C6—H6 119.9 H2A—C2—H2C 109.5 C8—C7—C6 119.55 (10) H2B—C2—H2C 109.5 C8—C7—H7 120.2 N1—C3—C3i _{108.95 (11) C6—C7—H7 120.2} N1—C3—H3A 109.9 C7—C8—C9 120.32 (10) C3i_{—C3—H3A 109.9 C7—C8—H8 119.8} N1—C3—H3B 109.9 C9—C8—H8 119.8 C3i_{—C3—H3B 109.9 C8—C9—C4 120.86 (10)} H3A—C3—H3B 108.3 C8—C9—H9 119.6 C5—C4—C9 118.12 (9) C4—C9—H9 119.6