1,1′-Binaphthyl-2,2′-dicarboxylic acid–urea (1/1)

Izotova, L.; Ashurov, J.; Talipov, S.; Ibragimov, B.; Weber, E.

doi:10.1107/S1600536808028997

Volume 64
Part 10
Page o1945
October 2008

Received 1 September 2008
Accepted 10 September 2008
Online 17 September 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.117
Data-to-parameter ratio = 11.5
Details

1,1'-Binaphthyl-2,2'-dicarboxylic acid-urea (1/1)

Lidiya Izotova,^a ^* Jamshid Ashurov,^a Samat Talipov,^a Bakhtiyar Ibragimov ^a and Edwin Weber ^b

^aInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, H. Abdullaev Street 83, Tashkent 100125, Uzbekistan, and ^bInstitute für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: l_izotova@yahoo.com

In the title co-crystal, C₂₂H₁₄O₄·CH₄N₂O, the 1,1'-binaphthyl-2,2'-dicarboxylic acid (BNDA) and urea molecules are connected via a system of hydrogen bonds into a chiral two-dimensional polymeric structure parallel to the (001) plane. As the crystal is centrosymmetric, it consists of alternately stacked BNDA-urea layers of opposite chirality. The urea H atoms trans to the C=O group are bonded in a chelating mode [R¹₂(6)] to the carbonyl O atom from one of the carboxylic acid groups which, in turn, acts as the donor of an O-HO hydrogen bond to another urea molecule. The [010] chains thus formed are further connected via an R²₂(8) hydrogen-bond motif formed between urea and the second carboxylic acid group of BNDA.

Related literature

For information on inclusion compounds of 1,1'-binaphthyl-2,2'-dicarboxylic acid, see: Weber (1996). For the synthesis of 1,1'-binaphthyl-2,2'-dicarboxylic acid, see: Weber et al. (1984).

Experimental

Crystal data

C₂₂H₁₄O₄·CH₄N₂O
M_r = 402.39
Monoclinic, P 2₁ /c
a = 9.2560 (19) Å
b = 12.033 (2) Å
c = 17.958 (4) Å
= 102.40 (3)°
V = 1953.5 (7) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 (2) K
0.21 × 0.17 × 0.12 mm

Data collection

Stoe STADI4 diffractometer
Absorption correction: none
3416 measured reflections
3416 independent reflections
2874 reflections with I > 2(I)
3 standard reflections every 100 reflections intensity decay: 2.1%

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.117
S = 1.09
3416 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO4	0.89 (3)	2.25 (3)	3.046 (3)	149 (2)
N1-H2NO1ⁱ	0.96 (3)	2.10 (3)	3.048 (3)	166 (2)
O2-H2O5ⁱⁱ	1.00 (3)	1.63 (3)	2.606 (2)	162 (2)
O3-H3O5ⁱⁱⁱ	0.98 (3)	1.70 (3)	2.637 (2)	160 (3)
N2-H3NO4	0.88 (3)	2.17 (3)	3.001 (3)	157 (3)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: STADI4 (Stoe & Cie, 1997); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2167 ).

Acknowledgements

Support of this research by the Uzbek Academy of Sciences (grant No. FA-F3-T141) is gratefully acknowledged.

References

Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1994). XP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Stoe & Cie (1997). STADI4 and X-RED. Stoe & Cie, Darmstadt, Germany.
Weber, E. (1996). Comprehensive Supramolecular Chemistry. Solid-State Supramolecular Chemistry: Crystal Engineering, Vol. 6, edited by D. D. MacNicol, F. Toda & R. Bishop, pp. 535-592. Oxford: Pergamon.
Weber, E., Csöregh, I., Stensland, B. & Czugler, M. (1984). J. Am. Chem. Soc. 106, 3297-3306.

organic compounds