Crystal structure of 5-phenylhydantoic acid ...

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The N- and C-bonded Η atoms were placed in calculated posi- tions and refined using a riding atom model with fixed distances. [Ν—H: 0.86 Ä, C(sp2 )—H: 0.93 ...

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Ζ. Kristallogr. N C S 2 1 5 (2000) 1 6 7 - 1 6 8 © by Oldenbourg Wissenschaftsverlag, München

Crystal structure of 5-phenylhydantoic acid, C6H5NHCONHCH2COOH R. Isea1, Μ. V. Capparelli*·1, D. Gomez11 and H. Gil" 1

Centre de Quimica, Instituto Venezolano de Investigaciones Cientificas (IVIC), Apartado 21827, Caracas 1020-A, Venezuela " Universidad de Los Andes, Facultad de Ciencias, Departamento de Quimica, Merida 5101, Venezuela Received August 7, 1999, CCDC-No. 1267/259

Table 1. Data collection and handling.

012

Crystal: Wavelength: μ: Diffractometer, scan mode:

white prism, size 0.38 χ 0.40 χ 0.59 mm Mo Ka radiation (0.71069 A) 1.07 cm" 1 Rigaku AFC7S, ω/2θ 49.96° 26max: N(hkl)measured, N(hkl)unique: 956, 956 Criterion for/ 0 bs, N(hkl)g 1: /obs > 2 a(/obJ, 887 141 N(param)re fined: Programs: TEXSAN [5], SAPI [6], SHELXL-93 [7], ZORTEP [8]

Abstract C9H10N2O3, o r t h o r h o m b i c , P 2 , 2 , 2 | ( N o . 19), a = 9 . 4 5 6 ( 6 ) Ä , b= 11.218(3) Ä , с = 8 . 6 5 8 ( 6 ) Ä , V= 9 1 8 . 4 Ä 3 , Z = 4 , Rgf(F) = 0 . 0 3 5 , wR(F2) = 0 . 0 9 1 , T= 2 9 8 K.

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

3"

Atom

Site

X

H(ll) H(2A) H(2B) H(3) H(5) H(52) H(53) H(54) H(55) H(56)

4a 4a 4a 4a 4a 4a 4a 4a 4a 4a

0.509(4) 0.7571(3) 0.8206(3) 0.7276(2) 0.7984(2) 0.7325(3) 0.7880(4) 0.9488(4) 1.0574(3) 1.0049(3)

Source of material T h e title c o m p o u n d w a s s y n t h e s i z e d as d e s c r i b e d e l s e w h e r e [ 1 ].

Discussion T h e N - a n d C - b o n d e d Η a t o m s w e r e p l a c e d in c a l c u l a t e d p o s i tions a n d r e f i n e d u s i n g a riding a t o m m o d e l w i t h f i x e d d i s t a n c e s [ Ν — H : 0.86 Ä, C ( s p 2 ) — H : 0.93 Ä, C ( s p 3 ) — H : 0.97 Ä] and l/iso. T h e O - b o n d e d Η a t o m ( H I 1) w a s r e f i n e d w i t h o u t c o n s t r a i n t s . A n e m0p. 0i r0i1c aχl Fc extinction o r r e c t i o nww [1 + λ / sin c(2Θ)] i tahst ah pe pplai er ad ms ue ct ehr that χ reF f icn*e =d кt oFac fi-

-0.396(3) -0.2898(2) -0.2513(2) -0.0993(2) 0.0804(2) 0.2852(2) 0.4699(2) 0.4869(3) 0.3181(3) 0.1325(2)

ζ

i/iso

0.531(4) 0.7782(3) 0.6187(3) 0.8378(2) 0.8288(2) 0.8062(3) 0.7064(4) 0.5069(4) 0.4125(3) 0.5122(3)

0.08(1) 0.059(8) 0.050(7) 0.054(8) 0.050(7) 0.060(8) 0.08(1) 0.067(9) 0.07(1) 0.066(9)

nal v a l u e of 0 . 0 2 0 ( 5 ) . A l l b o n d l e n g t h s are in g o o d a g r e e m e n t with t h e s t a n d a r d v a l u e s t a b u l a t e d [2]. T h e m o l e c u l e s a r e l i n k e d b y a t h r e e - d i m e n s i o n a l n e t w o r k of Ο — Η — O ( c a r b o n y l ) [ ί / ( 0 1 1 - 0 4 1 ' ) = 2 . 6 9 4 ( 3 ) Ä ] (i: - 0 . 5 + * , - O . 5 - 3 U - Z ) a n d N - H • · · О ( c a r b o n y 1) [ < / ( N 3 - 0 4 1 " ) = 3 . 1 1 3 ( 3 ) Ä ; < / ( N 5 - 0 4 1 ' ' ) = 2 . 9 6 7 ( 3 ) Ä ] (и: 1 . 5 - х , - у , 0 . 5 + г ) h y d r o g e n b o n d s . T h e p a t t e r n of t h e latter b o n d s is similar t o t h o s e f r e q u e n t l y o b s e r v e d in M W - d i s u b s t i t u t e d u r e a s [ 3 , 4 ] . Table 3. Atomic coordinates and displacement parameters (in Ä2). Atom

Site

C(l) 0(11) CK 12) C(2) N(3) C(4) 0(41) N(5) C(51) C(52)

4a 4a 4a 4a 4a 4a 4a 4a 4a 4a

0.6059(3) 0.5903(2) 0.5214(2) 0.7445(3) 0.7554(2) 0.8064(2) 0.8430(2) 0.8182(2) 0.8595(2) 0.7972(3)

-0.2640(2) -0.3803(2) -0.1917(2) -0.2362(2) -0.1152(2) -0.0269(2) -0.0418(1) 0.0796(2) 0.1897(2) 0.2914(2)

0.6141(2) 0.5951(2) 0.5731(3) 0.6913(3) 0.7455(2) 0.6591(2) 0.5218(2) 0.7319(2) 0.6662(2) 0.7257(3)



С/22

С/зз

0.043(1) 0.056(1) 0.056(1) 0.046(1) 0.053(1) 0.031(1) 0.0448(9) 0.059(1) 0.041(1) 0.055(2)

0.038(1) 0.0395(9) 0.0470(9) 0.039(1) 0.043(1) 0.041(1) 0.0432(8) 0.042(1) 0.041(1) 0.049(1)

0.040(1) 0.072(1) 0.085(1) 0.047(1) 0.0372(9) 0.0335(9) 0.0346(7) 0.0322(8) 0.038(1) 0.061(2)

* Correspondence author (e-mail: [email protected])

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и 12

0.000(1) -0.0023(8) 0.0076(9) -0.001(1) -0.0087(9) 0.0017(9) 0.0015(7) -0.0032(9) -0.003(1) 0.003(1)

и 13 -0.000(1) -0.020(1) -0.021(1) -0.005(1) 0.0010(9) -0.0015(9) 0.0022(7) 0.0048(9) -0.008(1) 0.002(1)

f/23

0.0042(9) -0.0023(8) 0.0023(9) 0.006(1) -0.0011(8) -0.0009(9) -0.0039(7) -0.0028(8) -0.0025(9) -0.005(1)

168

5 - P h e n y l h y d a n t o i c acid

Table 3. Continued. Atom

Site

X

У

г

U и

U22

t/зз

C(53) C(54) C(55) C(56)

4a

0.8308(4) 0.9272(4) 0.9913(3) 0.9595(3)

0.4020(2) 0.4125(3) 0.3113(3) 0.1999(2)

0.6662(4) 0.5481(4) 0.4916(3) 0.5503(3)

0.070(2) 0.076(2) 0.061(2) 0.045(1)

0.041(1) 0.052(2) 0.071(2) 0.051(1)

0.095(2) 0.080(2) 0.059(2) 0.049(1)

4a

4a 4a

References 1. Bergon, M.; Calmon, J.-P.: Kinetics and Mechanism of Hydantoic Ring Opening. The Alkaline Hydrolysis of 3-Arylimidazoline-2,4-diones to 5-Arylhydantoic Acids. J. Chem. Soc., Perkin Trans. II (1978) 493-497. 2. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R.: Tables of Bond Lengths determined by X-Ray and Neutron Diffraction. Part 1. Bond Lengths in Organic Compounds. J. Chem. Soc. Perkin Trans. II (1987) S1-S19. 3. Zhao, X.; Chang, Y.-L.; Fowler, F. W.; Lauher, J. W.: An Approach to the Design of Molecular Solids. The Ureylenedicarboxylic Acids. J. Am. Chem. Soc. 112 (1990) 6627-6634.

U12 0.004(1) -0.020(2) -0.028(2) -0.008(1)

U13 -0.014(2) -0.021(2) -0.005(2) -0.001(1)

ί/23 -0.003(2) 0.019(2) 0.008(2) -0.003(1)

4. Chang, Y.-L.; West, M.-A.; Fowler, F. W.; Lauher, J. W.: An Approach to the Design of Molecular Solids. Strategies for Controlling the Assembly of Molecules into Two-Dimensional Layered Structures. J. Am. Chem. Soc. 115 (1993) 5991-6000. 5. Molecular Structure Corporation. TEXSAN. Single Crystal Structure Analysis Software, Version 1.6 (Molecular Structure Corporation, The Woodlands, TX, USA 1993. 6. Fan, H. F.: SAPI-91. Structure Analysis Programs with Intelligent Control. Rigaku Corporation, Tokyo, Japan 1991. 7. Sheldrick, G. M.: SHELXL93. Program for Crystal Structure Refinement. University of Göttingen, Germany 1993. 8. Zsolnai, L., Pritzkow, H.: ZORTEP. ORTEP Program for Silicon Graphics. University of Heidelberg. Germany 1995.

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