4-Amino-8-cyclo­pent­yloxy-7-meth­oxy-2H-chromen-2-one monohydrate

Man-Hua Ding; Xiao-Ping Jiang

doi:10.1107/S160053681201450X

. 2012 Apr 18;68(Pt 5):o1397. doi: 10.1107/S160053681201450X

4-Amino-8-cyclopentyloxy-7-methoxy-2H-chromen-2-one monohydrate

Man-Hua Ding ^a,^*, Xiao-Ping Jiang ^a

PMCID: PMC3344523 PMID: 22590285

Abstract

The asymmetric unit of the title compound, C₁₅H₁₇NO₄·H₂O, contains two organic molecules with marginal differences between them and two water molecules. The chromine rings in both molecules are essentially planar, with maximum deviations of 0.012 (2) and 0.060 (2) Å. The five-membered cyclopentane rings adopt envelope conformations in both molecules. In the crystal, the components are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds, resulting in a three-dimensional network.

Related literature

For applications of the title compound in the treatment or prevention of disease, see: Scherlach et al. (2011 ▶); Luan et al. (2011 ▶); Yang et al. (2011 ▶). For a related structure, see: Doriguetto et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₇NO₄·H₂O
M _r = 293.31
Monoclinic,
a = 20.3651 (4) Å
b = 7.43162 (16) Å
c = 19.4049 (4) Å
β = 91.0792 (18)°
V = 2936.32 (11) Å³
Z = 8
Cu Kα radiation
μ = 0.83 mm⁻¹
T = 153 K
0.36 × 0.31 × 0.20 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2006 ▶) T _min = 0.754, T _max = 0.851
13804 measured reflections
5167 independent reflections
4701 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.193
S = 1.08
5167 reflections
394 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2006 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201450X/pv2524sup1.cif

e-68-o1397-sup1.cif^{(28KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201450X/pv2524Isup2.hkl

e-68-o1397-Isup2.hkl^{(247.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201450X/pv2524Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.88	1.99	2.861 (3)	172
N1—H1B⋯O2Wⁱⁱ	0.88	2.00	2.816 (3)	153
N2—H2A⋯O1ⁱⁱⁱ	0.88	2.03	2.888 (3)	166
N2—H2B⋯O1Wⁱ	0.88	2.08	2.838 (3)	144
O1W—H1AA⋯O5^iv	0.84	1.94	2.769 (3)	170
O2W—H2AB⋯O1^v	0.84	1.94	2.767 (3)	168
O1W—H1AB⋯O7	0.84	2.17	2.956 (3)	156
O1W—H1AB⋯O8	0.84	2.39	2.994 (3)	130
O2W—H2AA⋯O3	0.84	2.00	2.833 (3)	171
C7—H7⋯O2Wⁱⁱ	0.95	2.60	3.493 (3)	158
C15—H15B⋯O2W^vi	0.99	2.56	3.309 (4)	133

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

The authors thank the Scientific Research Fund of Hunan Provincial Education Department (10B039, 09B037, 11C0596) for financial support.

supplementary crystallographic information

Comment

The title compound belongs to a class of important medicinal intermediates which may be useful for the treatment or prevention of inflammatory and other diseases (Scherlach et al., 2011; Luan et al., 2011; Yang et al., 2011).

There are two crystallographically independent molecules of the title compound in an asymmetric unit labeled as molecule I (Fig. 1) and molecule II (Fig. 2) containing chromine rings (O2/C1–C9) and (O6/C16–C24), respectively. There are only marginal differences between the two molecules. The chromine rings (O2/C1–C9) and (O6/C16–C24) in both molecules are essentially planar with maximum deviations for atoms C9 and C16 being 0.012 (2) and 0.060 (2) Å, respectively. The five-membered cyclopentane rings adopt C14- and C29- envelope conformations with these atoms lying 0.581 (5) and 0.604 (5) Å, respectively, out of the planes formed by the remaining reings atoms. In the crystal, a three-dimensional network is established through the N—H···O, O—H···O and C—H···O hydrogen bonds which stabilizes the crystal structure (Fig. 3, Tab. 1).

Experimental

To a solution of 8-(cyclopentyloxy)-4-hydroxy-7-methoxy -2H-chromen-2-one (0.292 g) in toluene (10 ml) were added ammonium acetate (1.63 g) and acetic acid (1.26 g). The resulting mixture was stirred at reflux for 2 h. The water formed was removed azeotropically using a Dean-Stark apparatus, then toluene was also removed. The resulting solution was stirred for an additional 3 h at reflux. The reaction mixture was quenched with ice water (20 ml). A filtration was performed. The filter cake was washed three times with H₂O (20 ml). The solid was dried in an oven under reduced pressure and the product was recrystallized from ethyl acetate to afford yellow crystals of the title compound.