Crystal structure of (la,5ß,8ß,8aß)-l-methyl-l,2,3,5,8,8a-hexahydro-5,8- epoxychinolin(N-B)boran, C9HIONO(CH3)(BH3)

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600 Z. Kristallogr. NCS 215 (2000) ) by Oldenbourg Wissenschaftsverlag, München

Crystal structure of (la,5ß,8ß,8aß)-l-methyl-l,2,3,5,8,8a-hexahydro-5,8- epoxychinolin(N-B)boran, C

⁹

HIONO(CH

³

)(BH3)

K. Peters

¹

, E.-M. Peters*

¹

, S. Drinkuth", S. Groetsch

¹¹

and M. Christi

¹¹

I Max-Planck-Institut für Festkörperforschung, Heisenbergstraße 1, D-70506 Stuttgart, Germany

II Universität WUrzburg, Institut f ü r Organische Chemie, A m Hubland, D-97074 Würzburg, Germany Received April 12, 2000, CCDC-No. 1267/444

Table 1. Data collection and handling.

Abstract

CioHifiBNO, monoclinic, P 1 2 i / c l (No. 14), a = 7.764(1) À,

b = 17.758(2) Â, c = 7.869(1) Â, ß = 113.28(1)°, V = 996.6 Â3

,

Z = 4 , Rgt(F) = 0 . 0 5 6 , wRreffF2) = 0 . 1 6 5 , 7 = 2 9 3 K .

Source of material

The title compound was prepared by treatment of 5-bromo- 1 -methyl-1,2,3,6- tetrahydropyridin(N-B)boran in furan with po- tassium ieri-butoxide [1],

References

1. Groetsch, S.: Dissertation, Universität WUrzburg, Germany, in prepara- tion.

2. Sheldrick, G. M.: SHELXL-97, a program for refining crystal structures.

University of Göttingen, Germany 1997.

Table 3. Atomic coordinates and displacement parameters (in Â2).

Crystal: colourless, plate, size 0.15 x 0.45 x 0.5 mm Wavelength: M o Ka radiation (0.71073 À)

n: 0.74 cm"1

Diffractometer, scan mode: Bruker AXS, co

29max: 54.98°

N(hkl)mcasured, N(hkl)miquc- 2919, 2258 Criterion for /0bs, N(hkl)gC. /obs > 2 crf/obs), 1542

N(param)rci\nci- 118

Program: SHELXL-97 [2]

Table 2. Atomic coordinates and displacement parameters (in Â2).

Atom Site X y z Uiso

H(2A) 4e -0.1671 - 0 . 1 9 3 7 - 0 . 2 2 3 4 0.08 H(2B) 4e - 0 . 0 7 8 4 - 0 . 1 1 3 5 - 0 . 2 0 8 0 0.08 H(3A) 4e - 0 . 2 5 5 7 - 0 . 0 8 4 6 - 0 . 5 0 2 3 0.08 H(3B) 4e - 0 . 2 1 0 7 - 0 . 1 6 9 8 - 0 . 5 1 6 5 0.08 H(4) 4e - 0 . 5 4 2 1 - 0 . 1 5 4 4 - 0 . 6 8 3 6 0.08 H(6) 4e - 0 . 4 5 0 5 - 0 . 2 1 2 7 - 0 . 2 0 3 6 0.08 H(7) 4e - 0 . 6 5 4 4 - 0 . 1 5 5 7 - 0 . 0 7 6 2 0.08 H(8) 4e - 0 . 7 7 5 8 - 0 . 0 3 2 0 - 0 . 2 3 2 0 0.08 H(9) 4e - 0 . 9 1 0 0 - 0 . 0 5 4 6 - 0 . 5 6 4 2 0.08 H(10) 4e - 0 . 8 6 5 3 - 0 . 1 9 2 1 - 0 . 6 1 6 1 0.08 H( 12A) 4e - 0 . 1 9 6 2 - 0 . 1 7 2 1 0.0855 0.08 H(12B) 4e - 0 . 3 0 5 4 -0.1011 0.1074 0.08 H(12C) 4e - 0 . 1 0 8 5 - 0 . 0 9 1 7 0.0984 0.08 H(13A) 4e - 0 . 4 4 5 0 - 0 . 0 1 2 5 - 0 . 1 6 1 2 0.08 H(13B) 4e - 0 . 4 2 2 6 - 0 . 0 2 5 4 - 0 . 3 4 8 5 0.08 H(13C) 4e - 0 . 2 4 8 0 - 0 . 0 0 3 2 - 0 . 1 7 0 3 0.08

Atom Site Un Un Un Un U13 Un

N ( l ) 4e - 0 . 3 2 3 2 ( 2 ) - 0 . 1 1 2 0 2 ( 9 ) -0.1702(2) 0.0346(8) 0.0391(8) 0.0336(7) - 0 . 0 0 1 5 ( 6 ) 0.0083(6) 0.0006(6) C(2) 4e -0.1954(3) - 0 . 1 4 1 3 ( 1 ) -0.2577(3) 0.036(1) 0.056(1) 0.052(1) 0.0018(9) 0.0140(9) -0.0042(9) C(3) 4e -0.2768(3) - 0 . 1 3 5 1 ( 1 ) -0.4681(3) 0.050(1) 0.060(1) 0.051(1) - 0 . 0 0 3 ( 1 ) 0.025(1) -0.009(1) C(4) 4e - 0 . 4 8 2 1 ( 3 ) - 0 . 1 5 2 1 ( 1 ) -0.5554(3) 0.049(1) 0.046(1) 0.0366(9) 0.0015(9) 0.0138(9) -0.0078(8) C(5) 4e - 0 . 5 7 8 3 ( 3 ) - 0 . 1 6 3 6 ( 1 ) -0.4540(2) 0.0376(9) 0.0321(9) 0.0379(9) -0.0010(7) 0.0074(8) -0.0038(7) C(6) 4e - 0 . 4 9 3 2 ( 3 ) - 0 . 1 6 1 4 ( 1 ) -0.2450(2) 0.0390(9) 0.0353(9) 0.0374(9) -0.0031(7) 0.0097(7) 0.0041(7) C(7) 4e - 0 . 6 7 1 4 ( 3 ) - 0 . 1 4 8 4 ( 1 ) -0.2053(3) 0.044(1) 0.064(1) 0.040(1) - 0 . 0 0 6 5 ( 9 ) 0.0173(9) 0.0062(9) C(8) 4e - 0 . 7 6 8 5 ( 3 ) - 0 . 0 7 6 1 ( 1 ) -0.2926(3) 0.038(1) 0.059(1) 0.055(1) -0.0015(9) 0.0214(9) - 0 . 0 0 7 ( 1 ) C(9) 4e - 0 . 8 4 0 6 ( 3 ) - 0 . 0 8 8 3 ( 1 ) -0.4721(3) 0.0334(9) 0.051(1) 0.051(1) 0.0016(8) 0.0111(8) 0.0010(9) C(10) 4e - 0 . 7 8 7 9 ( 3 ) - 0 . 1 6 8 1 ( 1 ) -0.4985(3) 0.038(1) 0.048(1) 0.044(1) -0.0062(8) 0.0081(8) -0.0037(9) O ( I l ) 4e - 0 . 7 8 7 1 ( 2 ) - 0 . 2 0 3 9 9 ( 9 ) -0.3333(2) 0.0483(8) 0.0551(9) 0.063(1) -0.0159(7) 0.0173(7) 0.0082(7) B(12) 4e - 0 . 2 2 3 1 ( 4 ) - 0 . 1 2 0 1 ( 2 ) 0.0530(3) 0.057(2) 0.064(2) 0.035(1) - 0 . 0 0 1 ( 1 ) 0.003(1) 0.002(1) C(13) 4e - 0 . 3 6 3 3 ( 3 ) - 0 . 0 3 1 1 ( 1 ) -0.2166(3) 0.048(1) 0.039(1) 0.043(1) - 0 . 0 0 6 2 ( 8 ) 0.0126(9) -0.0023(8)

* C o r r e s p o n d e n c e author

(e-mai 1 : peters @ v s i b m 1 . m p i - s t u t t g a r t . m p g . d e )

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Z. Kristallogr. N C S 215 (2000) 6 0 1 - 6 0 2

© by Oldenbourg Wissenschaftsverlag, München

601

Crystal structure of 6,7-dihydro-5,7-methano-5//-cycIopenta[i/]pyridazin- 1,4-dicarboxylic acid dimethyl ester, C12H12N2O4

K. Peters

1

, E.-M. Peters*

1

, C. Cohrs", H. Reuchlein" and M. Christi"

1 Max-Planck-Institut für Festkörperforschung, Heisenbergstraße 1, D-70506 Stuttgart, Germany

" Universität Würzburg, Institut für Organische Chemie, Am Hubland, D-97074 Würzburg, Germany Received April 20, 2000, CCDC-No. 1267/445

Abstract

C12H12N2O4, orthorhombic, Prima ( N o . 6 2 ) , a = 2 1 . 4 9 1 ( 3 ) A , b = 6 . 8 9 0 0 ( 8 ) A , c = 7 . 8 3 9 9 ( 8 ) A , V= 1 1 6 0 . 9 A3, Z = 4, Rgt(F) = 0 . 0 5 3 , wRKf{F2) = 0 . 1 6 2 , 7 = 2 9 3 K.

Source of material

T h e title c o m p o u n d w a s prepared b y reaction o f dimethyl- l , 2 , 4 , 5 - t e t r a z i n e - 3 , 6 - d i c a r b o x y l a t e w i t h b i c y c l o [ 2 . 1 . 1 ] h e x - 2 - e n e and d e h y d r o g e n a t i o n of the product by 4 , 5 - d i c h l o r o - 3 , 6 - d i o x o c y c l o h e x a - l , 4 - d i e n e - l , 2 - d i c a r b o n i t r i l e [1, 2],

Table 3. Atomic coordinates and displacement parameters (in A2).

Table 1. Data collection and handling.

Crystal: colourless prism, size 0.15 x 0.2 x 0.45 mm Wavelength: Mo Ka radiation (0.71073 Â)

1.08 cm"1

Diffractometer, scan mode: Bruker AXS, œ

29max: 55°

N(hkl)measured, N(hkl)anique: 3746, 1442 Criterion for /0bs, N(hkl)tc /obs > 2 crf/obs), 1002 N(param) refined: 115

Program: SHELXL-97 [3]

Table 2. Atomic coordinates and displacement parameters (in Ä²).

Atom Site X _y _z U¡,o

H(5) 4c 0.6693 1/4 0.8280 0.053(8)

H(6) 4c 0.4922 1/4 0.9368 0.07(1)

H(7A) 8 d 0.5921 0.0747 1.0266 0.070(7)

H(7B) 8 d 0.5778 -0.0231 0.8447 0.055(6)

H(12A) 4c 0.7560 1/4 0.0817 0.17(2)

H(12B) 8 d 0.7752 0.3638 0.2467 0.15(1)

H(15A) Ac 0.3326 1/4 0.8903 0.13(2)

H(15B) 8 d 0.3186 0.3638 0.7214 0.15(1)

Atom Site x y z U¡¡ U22 t/33 U12 U13 t/23

N(l) 4c 0.51028(9) 1/4 0.3825(3) 0.041(1) 0.059(1) 0.034(1) 0 -0.0036(9) 0

N(2) 4c 0.5701(1) 1/4 0.3477(2) 0.043(1) 0.062(1) 0.030(1) 0 -0.0008(8) 0

C(3) 4c 0.6125(1) 1/4 0.4756(3) 0.037(1) 0.046(1) 0.033(1) 0 -0.0001(9) 0

C(4) 4c 0.5950(1) 1/4 0.6438(3) 0.037(1) 0.050(1) 0.031(1) 0 -0.0023(9) 0

C(5) 4c 0.6245(1) 1/4 0.8190(3) 0.043(1) 0.081(2) 0.032(1) 0 -0.007(1) 0

C(6) 4c 0.5310(1) 1/4 0.8746(3) 0.052(2) 0.067(2) 0.028(1) 0 0.005(1) 0

C(7) 8 d 0.58267(9) 0.0974(3) 0.9073(2) 0.065(1) 0.071(1) 0.0316(8) 0.005(1) -0.0044(8) 0.008(1)

C(8) 4c 0.5311(1) 1/4 0.6813(3) 0.040(1) 0.046(1) 0.030(1) 0 0.002(1) 0

C(9) 4c 0.4902(1) 1/4 0.5469(3) 0.037(1) 0.043(1) 0.036(1) 0 -0.0030(9)" 0

C(10) 4c 0.6798(1) 1/4 0.4258(4) 0.041(1) 0.063(2) 0.041(1) 0 0.004(1) 0

O(10) 4c 0.7206(1) 1/4 0.5277(3) 0.039(1) 0.209(4) 0.059(1) 0 -0.002(1) 0

0(11) 4c 0.68907(9) 1/4 0.2605(3) 0.048(1) 0.098(2) 0.049(1) 0 0.0164(9) 0

C(12) 4c 0.7532(2) 1/4 0.2033(5) 0.052(2) 0.120(3) 0.079(2) 0 0.032(2) 0

* Correspondence author

(e-mail: peters@vsibml .mpi-stuttgart.mpg.de)

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602

C12H12N2O4

Table 3. Continued.

Atom S i t e X y z Un U22 U33 Un U\i t / 2 3

C ( 13 ) 4c 0.4206(1) 1 / 4 0.5650(3) 0.039(1) 0.046(2) 0.049(2) 0 -0.000(1) 0

CK 13) 4c 0.3850(1) 1/4 0.4496(3) 0.042(1) 0.141(2) 0.062(1) 0 -0.015(1) 0

0 ( l 4) 4c 0.40443(9) 1/4 0.7274(3) 0.0355(9) 0.096(2) 0.059(1) 0 0.0099(9) 0

C(15) 4c 0.3390(1) 1/ 4 0.7669(5) 0.039(2) 0.082(2) 0.087(3) 0 0.020(2) 0

References

1. Reuchlein, H.: Synthesen in der Bicyclo[2.2. l]hexan-Reihe. Dissertation, University of Würzburg, Germany 1990.

2. Cohrs, C.: Unpublished results, University of Würzburg, Germany 2000.

3. Sheldrick, G. M.: SHELXL-97, a program for refining crystal structures.

University of Göttingen, Germany 1997.