(E)-1-(4-Methoxyanthracen-1-yl)-2-phenyldiazene

(1)

( E )-1-(4-Methoxyanthracen-1-yl)-2- phenyldiazene

Aurelien Crochet,^aKatharina M. Fromm,^a* Vanya Kurteva^band Liudmil Antonov^b*

aUniversity of Fribourg, Department of Chemistry, Chemin du Musee 9, CH-1700 Fribourg, Switzerland, and^bInstitute of Organic Chemistry, Bulgarian Academy of Sciences, Acad. G. Bonchev str., bdg 9, Sofia 1113, Bulgaria

Correspondence e-mail: katharina.fromm@unifr.ch, lantonov@orgchm.bas.bg Received 10 February 2011; accepted 23 March 2011

Key indicators: single-crystal X-ray study;T= 150 K; mean(C–C) = 0.004 A˚;

Rfactor = 0.047;wRfactor = 0.086; data-to-parameter ratio = 11.9.

The title compound, C21H16N2O, has anE-conformation about the diazene N N bond. It is reasonably planar with the phenyl ring being inclined to the mean plane of the anthracene moiety [planar to within 0.077 (3) A˚ ] by 6.43 (10). The crystal structure is stabilized by C—H and weak–interactions [centroid–centroid distances of 3.7192 (16) and 3.8382 (15) A˚ ], leading to the formation of two-dimensional networks stacking along [001] and lying parallel to (110).

Related literature

For background to sensing molecules based on tautomeric switches, see: Nedeltchevaet al.(2009); Antonovet al.(2009, 2010). For investigations of the tautomerism of azodyes, see:

Kelemen (1981). For the synthesis of the title compound, see:

Nedeltchevaet al.(2010).

Experimental

Crystal data

C21H16N2O M_r= 312.36

Orthorhombic,P212121

a= 6.3021 (3) A˚ b= 9.0481 (4) A˚ c= 27.3935 (17) A˚ V= 1562.03 (14) A˚³

Z= 4

MoKradiation = 0.08 mm¹ T= 150 K

0.540.320.12 mm

Data collection

STOE IPDS 2T diffractometer 12181 measured reﬂections 2584 independent reﬂections

2096 reﬂections withI> 2(I) Rint= 0.072

Reﬁnement

R[F²> 2(F²)] = 0.047 wR(F²) = 0.086 S= 1.10 2584 reﬂections

218 parameters

H-atom parameters constrained max= 0.13 e A˚³

min=0.15 e A˚³

Table 1

C—H interactions (A˚ ,).

Cg1,Cg2 andCg3 are the centroids of the C1–C6, C7,C8,C17–C20 and C8–

C10,C15–C17) rings, respectively.

C—H Cg C—H H Cg C Cg C—H Cg

C21—H21A Cg1ⁱ 0.98 2.83 3.646 (4) 141

C12—H12 Cg2ⁱⁱ 0.95 2.80 3.681 (4) 154

C11—H11 Cg3ⁱⁱ 0.95 2.83 3.543 (3) 132

Symmetry codes: (i)xþ1;yþ1;z; (ii)xþ2;yþ¹2;zþ¹2.

Data collection:X-AREA(Stoe & Cie, 2009); cell reﬁnement:X- AREA; data reduction: X-RED32 (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97(Sheldrick, 2008); program(s) used to reﬁne structure: SHELXL97 (Sheldrick, 2008); molecular graphics:PLATON(Spek, 2009) andMercury(Macraeet al., 2006);

software used to prepare material for publication: SHELXL97, PLATONandpublCIF(Westrip, 2010).

The authors thank the Bulgarian National Science Fund (Project TK–X-1716), the SCOPES program of the Swiss National Science Foundation and FriMat for generous funding. They also thank Professor Helen Stoekli-Evans for valuable advice and assistance.

Supplementary data and ﬁgures for this paper are available from the IUCr electronic archives (Reference: NC2221).

References

Antonov, L., Deneva, V., Simeonov, S., Kurteva, V., Nedeltcheva, D. & Wirz, J.

(2009).Angew. Chem. Int. Ed.48, 7875–7878.

Antonov, L. M., Kurteva, V. B., Simeonov, S. P., Deneva, V. V., Crochet, A. &

Fromm, K. (2010).Tetrahedron,66, 4292–4297.

Kelemen, J. (1981).J. Dyes Pigm.2, 73–91.

Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006).J. Appl. Cryst.39, 453–457.

Nedeltcheva, D., Antonov, L., Lycka, A., Damyanova, B. & Popov, S. (2009).

Curr. Org. Chem.13, 217–240.

Nedeltcheva, D., Kurteva, V. & Topalova, I. (2010).Rapid Commun. Mass Spectrom.24, 714–720.

Sheldrick, G. M. (2008).Acta Cryst.A64, 112–122.

Spek, A. L. (2009).Acta Cryst.D65, 148–155.

Stoe & Cie (2009).X-AREAandX-RED32. Stoe & Cie GmbH, Darmstadt, Germany.

Westrip, S. P. (2010).J. Appl. Cryst.43, 920–925.

organic compounds

Acta Cryst.(2011). E67, o993 doi:10.1107/S1600536811010932 Crochetet al.

o993

Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

(2)

(3)

!"#" $

%& !'() **'+(, -.%-

!"#$% & '(%

%)!*!+! , -&( % #$% .%!)%

)#%#% /% #! %#*

*##%%%%!!$**!#0*% !%!)#% &

1#!(0( .%!)% 2*$!"!&%##

)$ $#!%)$!!$1#!( 3# $!#

$!#((&%# #!!#'% (!$#% & # -&$!%%! %# #!!!%2$!"!

3 !%!%%! !%!&43 !%!& )%

#"151)#!(!$!&$!6768 )!# *!

$6976 )$82 :

/$! !%!!'#)$67-;;;<3)! 3!&'<;;;<(!(

*$!6768 &696,6976

#6,766=769

$ $# >

###98 #,,= ?*(!$3!#

&# !!'&''!!$!!!!4

@ ! $! 2$!#"$! !) #($*)! %!

%### $!#((&$!##2*(!$1#!(

A'#)!'!'$!! *%#%)!B$#!$&&)$!&#%

! !%! *%#

C%($ *)!%%%#)!%%)# #3 4#!**& # 36)%#- &!%##!%!#*##

# D67-E=#,?6-#6-

- *(!$&

- E'F

_.

6 &'E

=6- - #'E!!-

(4)

40(& !%!%%! %#&!)!##!

!!##&=))!$!(!

40(&!$!%%! *%#3<;;;<#

67-;;;<#&##$!3)!#!>- (!(#() #!$

!"

6-81G E8=8 E8 E, ^H

G ) I#JE99?

-!!$ )!DK) 6!!* ,9!

E8 ? LE=M=:

E2,2 ? NE, ^H E9=9 ? E=+

E=82 ? C!'#

E2 =2FF

! "

@3G/KA@3

# 8!&#OP#

Q#%D%!#%) $E9

* L E28:L E=:

A!%D889*! %EH8R9 # &EHR

, %#! EHR

=,2#*#!

$'!"("

Q K $ !D%%(#

#

(5)

$

S.% D%!! @#$ !D#4% *

$OP E29 -$#!D# )%

)$ E,8 - * #

*E )ETP U2 U=

&EU T

=,2! VTP W

,* VX E?^H

VX EH=?^H

*+!!

/* 0!!%Y*%##!!)&&!*! #%%!!( 3

!!%Y'%#(#%!!$ %Y#!#!>!)&

%Y!!* !$%#&$##)$$!$ $0** * !!%Y

%# %Y(!(!*!

01 *Q 0SS!3&#$)$##*)#(!

$$)#&"(3!#*OP %#!$!%!$

#!(! $)#!!$)%&!

)##$)#0SS#&!!)(!

! " (! !""! +! ,-!."! +!!+("+(/0

¹

2

ZT.

6 922 H9 28, =8

6 2 H, 2=2 9

- 8 H2 2,= 29Z

6 == H9,9 2229 2=,

- H2 H 298 ==Z

62 8= H29 2=8 2,,

-2 H= H=8 2, =Z

6= == H2 89= 29

-= 8 H, 9 2Z

68 2 H22, 92 28

-8 2 H2, 28 2Z

69 ,282 2 8, 98

6, ,,2 2 =8, 9,8

6 22 82 , ,8

- , 9= 89 9Z

6 9=2 88 99, ,98 6 8=8= H, 9,,, =8

- 8 H8, = 2Z

6 8= H,9 8=, =9

- ,9= H8, 8 2Z

6 22 9= 9=9 ==9

- == 98 9 2Z

62 22,2 2,9 , ,8

(6)

-2 =8,, 2, Z

6= 2 29 99=, ,8

68 =2 9 ,, 8

-8 2=8 ,, = =Z

69 9,2 =,9, =,8

6, ,2 = 2=,, ,28

6 =2 , 299=, 8

- 8 9 28=8 8Z

6 ,882 , 2, 9

- 9899 ,= 2=,9 Z

6 2,== 2,2 222, 29

-0 8= ==,= 229 8Z

-C =8=8 =9 2 8Z

-6 2 29 292 8Z

1 =22 9 2=99 =

1 8=9 28= ,99 =

G ,= = 2=88 29=

(!!+("+(/0

¹

2

6 == 9=8 9= , =

6 ,=, 89 2,2 H2 9= H, 6 8, 22 =99 H98 ,= H2=

62 = , 8 2 == H2

6= 99, =, =8 H2= H82 H

68 8 28 = 92 2

69 = ,8 H2 8

6, 2= ,= 8 H 9

6 =2 28 H H2

6 9= 92= 2 = H,

6 =98 28 H, H2= H9

6 29 89 ,= H,2 H9 H8

6 8=9 99 82 = 29 H

62 8 =8 9, H2 =

6= 2= == 9 H =

68 29= ,8 2 H8

69 =2= 8= = 9 H,

6, 8== 9=8 H= H2,

6 88 28 98 H= H,

6 8 8,9 ,= 82 ,

6 28, 2, 2 H= H88 H88

1 = 2 =

1 28 2 = = 2

G = , H,8 H8, H8=,

3 (!+(/0452

676 9 67- =

(7)

%

6768 , 676 282

671 2= 67- =

676 22 6762 =,

67- = 67- =

6762 92 6276= 2=

67- = 627-2 =

6276= 9,2 6=768 ,

627-2 = 68769

6=768 ,82 687-8 =

6=7-= = 6976, 2

687-8 = 6,7G =

6976 =8 6,76 9

6971 2 676 22

6976, 22 67- =

6,76 67- =

6,769 222 67G 22

676 67-0 ,

67- = 67-C ,

676 2 67-6 ,

676= 292 171 82

676 =,2

676768 6767- 9

67671 =9 627676 8

687671 2 62767- 9

67676 6767- 9

6767- 676276= 9

6767- 67627-2 9

627676 6=7627-2 9

62767- 6876=762

6767- 6876=76 ,8

676276= 6276=76

67627-2 6976876= ,

6=7627-2 697687-8

6276=768 6=7687-8

6276=7-= , 6876976, 8

6876=7-= , 6876976, 2

6=76876 8 6,76976, ,

6=7687-8 G76,76 ==

67687-8 G76,769 2

676971 = 676,769

676976, 6,7676

176976, 28 6,767- 2

676,769 ,, 6767- 2

676,769 697676 =

6976,769 9 69767- ,9

6,7676 9 6767- ,9

6,767- G767-0 =

6767- G767-C =

67676 2 -0767-C =

(8)

&

67676= = G767-6 =

67676= , -0767-6 =

67676 -C767-6 =

6767- = 17176 =

6767- = 171769 =

67676 = 6,7G76 9=

6767- 9

68767676 H2 67676=762 92 1767676 9,2 6276=768769 9, 67676762 2 676=768769 H22 67676276= 2 6=76876976, H98 676276=768 H2 6=76876976, =2 6276=76876 H=2 676,769768 H2 67676876= 82 6976,769768 989 17676876= H9, 676,76976, 99 676976,76 H9=, 6976,76976, H 176976,76 2 6876976,7G

676976,769 =2 6,76976,7G H9,2 176976,769 H98 6876976,76 92 6976,7676 2 6,76976,76 2 6976,7676 H9,, G76,7676 H9 6,767676 H9 6976,7676 92 6,767676= 92 17697676 9,, 6767676 H, 6,7697676 H82 6=767676 H2 6,7676769 H=2

6767676 2 6767171 H9

67676762 H82 68767171 8=

67676276= 22 67171769 98 676276=768 H9 67697171 H2 676276=76 H22 6,7697171 892 67676=768 H92 676,7G76 2 67676=768 9 6976,7G76 H9=

67676=762 99

6 7" "7 (/0452

66#6#6M68696,69M6#6,M66=M69 *(!$

7-;;; 7- -;;; ;;; 7-;;;

67-0;;;6 , , 8282 2

67-;;;6 = , 8,2 =2

67-;;;6 = , =2

@$ $#D UU> HUUTHUT

(9)

'

#

(10)

(

#

(E)-1-(4-Methoxyanthracen-1-yl)-2-phenyldiazene