Ethyl 2-amino-4-(4-bromo­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate

El-Agrody, A.M.; Fouda, A.M.; Al-Omar, M.A.; Amr, A.E.-G.E.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681300490X

Volume 69
Part 3
Pages o435-o436
March 2013

Received 19 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R = 0.060
wR = 0.164
Data-to-parameter ratio = 17.6
Details

Ethyl 2-amino-4-(4-bromophenyl)-6-methoxy-4H-benzo[h]chromene-3-carboxylate

Ahmed M. El-Agrody,^a,^b Ahmed M. Fouda,^a Mohamed A. Al-Omar,^c,^d Abd El-Galil E. Amr,^d,^e ⁺ Seik Weng Ng ^f,^g and Edward R. T. Tiekink ^f ^*

^aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia,^bChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt,^cDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,^dDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,^eApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt,^fDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^gChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

In the title compound, C₂₃H₂₀BrNO₄, the pyran ring has a flattened boat conformation with the O and methine C atoms lying to one side of the plane [0.160 (5) and 0.256 (6) Å, respectively] defined by the remaining atoms. Nevertheless, the 4H-benzo[h]chromene ring system approximates a plane (r.m.s. deviation = 0.116 Å) with the bromobenzene ring almost perpendicular [dihedral angle = 83.27 (16)°] and the ester group coplanar [C-C-C-O = 3.4 (5)°]; the methoxy substituent is also coplanar [C-O-C-C = 174.5 (3)°]. In addition to an intramolecular N-HO(ester carbonyl) hydrogen bond, the ester carbonyl O atom also forms an intermolecular N-HO hydrogen bond with the second amine H atom, generating a zigzag supramolecular chain along the c axis in the crystal packing. The chains are linked into layers in the bc plane by N-HBr hydrogen bonds, and these layers are consolidated into a three-dimensional architecture by C-H [pi] interactions.

Related literature

For background to the pharmaceutical activity of 4H-chromene and its derivatives, see: Abd-El-Aziz et al. (2004, 2007); Kemnitzer et al. (2007); Alvey et al. (2009). For the isostructural 4-fluoro analogue, see: El-Agrody et al. (2012).

Experimental

Crystal data

C₂₃H₂₀BrNO₄
M_r = 454.31
Monoclinic, P 2₁ /c
a = 13.1543 (14) Å
b = 16.8110 (18) Å
c = 9.3672 (12) Å
= 96.628 (10)°
V = 2057.6 (4) Å³
Z = 4
Mo K radiation
= 2.03 mm^-1
T = 295 K
0.30 × 0.20 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.828, T_max = 1.000
12041 measured reflections
4740 independent reflections
2533 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.164
S = 1.02
4740 reflections
270 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.91 e Å^-3
_min = -0.90 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1,C2,C7-C10, C17-C22 and C2-C7 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N1-H2O2	0.88 (1)	2.09 (5)	2.744 (5)	131 (5)
N1-H1O2ⁱ	0.88 (1)	2.22 (2)	3.075 (5)	163 (3)
N1-H2Br1ⁱⁱ	0.88 (4)	2.76 (4)	3.547 (4)	149 (5)
C4-H4Cg1ⁱ	0.93	2.90	3.673 (5)	142
C6-H6Cg2ⁱⁱⁱ	0.93	2.98	3.743 (5)	140
C23-H23CCg3ⁱⁱⁱ	0.96	2.70	3.593 (5)	154
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5295 ).

Acknowledgements

The authors are grateful for the sponsorship of the Research Center, College of Pharmacy and the Deanship of Scientific Research, King Saud University. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Abd-El-Aziz, A. S., El-Agrody, A. M., Bedair, A. H., Corkery, T. C. & Ata, A. (2004). Heterocycles, 63, 1793-1812.
Abd-El-Aziz, A. S., Mohamed, H. M., Mohammed, S., Zahid, S., Ata, A., Bedair, A. H., El-Agrody, A. M. & Harvey, P. D. (2007). J. Heterocycl. Chem. 44, 1287-1301.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Alvey, L., Prado, S., Saint-Joanis, B., Michel, S., Koch, M., Cole, S. T., Tillequin, F. & Janin, Y. L. (2009). Eur. J. Med. Chem. 44, 2497-2505.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
El-Agrody, A. M., Al-Omar, M. A., Amr, A.-G. E., Chia, T. S. & Fun, H.-K. (2012). Acta Cryst. E68, o1803-o1804.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kemnitzer, W., Drewe, J., Jiang, S., Zhang, H., Zhao, J., Crogan-Grundy, C., Xu, L., Lamothe, S., Gourdeau, H., Denis, R., Tseng, B., Kasibhatla, S. & Cai, S. X. (2007). J. Med. Chem. 50, 2858-2864.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds