4-{[Bis(2-hy­droxy­eth­yl)amino]­meth­yl}-6-meth­oxy-2H-chromen-2-one

Naik, R.; Sankolli, R.; Anil Kumar, G.N.; Row, T.N.G.; Kulkarni, M.V.

doi:10.1107/S1600536812030759

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2413-o2414

https://doi.org/10.1107/S1600536812030759

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4-{[Bis(2-hydroxyethyl)amino]methyl}-6-methoxy-2H-chromen-2-one

Reshma Naik,^a Ravish Sankolli,^b G. N. Anil Kumar,^c T. N. Guru Row ^b and Manohar V. Kulkarni ^a ^*

^aP.G. Department of Chemistry, Karnatak University, Dharwad 580 003, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India, and ^cDepartment of Physics, M.S. Ramaiah Institute of Technology, Bangalore 560054, India
^*Correspondence e-mail: manohar274@gmail.com

(Received 6 June 2012; accepted 5 July 2012; online 10 July 2012)

In the title compound, C₁₅H₁₉NO₅, an intramolecular O—H⋯O hydrogen bond links the hydroxyethyl side chains, forming a seven-membered ring. In the crystal, molecules are linked into chains via O—H⋯O hydrogen bonds along the b axis. Further, molecules are linked by weak intermolecular C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.707 (4) Å].

Related literature

For the properties of coumarins, see: Meng et al. (1989 ); Baures et al. (2002 ); Jadhav et al. (2010 ); Basanagouda et al. (2011 ); Kokila et al. (1995 ); Khan et al. (2008 ). For 4-bromomethyl-6-methoxy-2H-chromen-2-one, see: Basanagouda et al. (2011). For aromatic compounds containing a β-hydroxyethyl side chain, see: Khan et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For C—H ⋯O interactions, see: Desiraju (2005 ). For stacking interactions, see: Janiak (2000 ). For related literature on 4-bromomethyl-2H-chromen-2-one, see: Basanagouda & Kulkarni (2011 ).

Experimental

Crystal data

C₁₅H₁₉NO₅
M_r = 293.31
Monoclinic, P 2₁ /c
a = 9.3038 (5) Å
b = 7.9290 (5) Å
c = 19.6216 (12) Å
β = 92.944 (5)°
V = 1445.56 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 123 K
0.2 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.98, T_max = 0.982
14012 measured reflections
2694 independent reflections
1994 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.149
S = 1.02
2694 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4ⁱ	0.84	1.85	2.685 (3)	174
O4—H4A⋯O3	0.84	2.06	2.875 (3)	164
C7—H7⋯O5ⁱⁱ	0.95	2.56	3.494 (2)	167
C14—H14B⋯O2ⁱⁱⁱ	0.99	2.48	3.206 (3)	130
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x, -y, -z+1.

Data collection: SMART (Bruker, 2008); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and CAMERON (Watkin et al., 1996 ); software used to prepare material for publication: PARST (Nardelli, 1995 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812030759/zj2082sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030759/zj2082Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812030759/zj2082Isup3.cml

checkCIF report

Comment top

Coumarins have been shown to be important molecular models, revealing different aspects of solid state organic chemistry. Derivatives of coumarin have been investigated for their solid state dimerisation (Meng et al., 1989), self association in the solid state (Baures et al., 2002), and host of other interesting features which have come to light by their crystal structure studies (Jadhav et al., 2010). Our earlier studies have shown that 4-aryloxymethyl coumarins exhibit a Head-tail packing (Gupta et al., 2011), whereas 4-arylamino methyl coumarins exhibit a layer like arrangement (Kokila et al., 1995) in solid state.

Diethanol amines are the key intermediate in the synthesis of nitrogen mustards and there are few reports on the structures possessing β-hydroxy ethyl side chain (Khan et al., 2008). In the light of above observations it was thought of considerable interest to study the title compound (Fig. 1) which was intermediate in a series of Nitrogen mustards synthesised for their anti-cancer activities.

The X-ray crystal structures of the title compound reveal that molecule is non-planar. The diethanol amine side chain is oriented towards the coumarin ring with the nitrogen being out of the plane of the molecule shown by the dihedral angles of C7-C8-C11-N1 -122.53 (2)° and C9-C8-C11-N1 62.23 (2)° . The shortened C2-O5 bond distance of 1.371 (3)Å compared to the C1-O5 bond distance of 1.417 (3) Å indicates the delocalization of lone pair of electrons on the O5 oxygen atom across the coumarin ring. The crystal structure of the compound is stabilized by of both intra and intermolecular O-H···O hydrogen bonds and inter molecular C-H···O interactions. The intramolecular O-H···O hydrogen bond connects diethanol amine side chains. In the solid state, molecules are linked via O-H···O hydrogen bonds. Further molecules are connected by weak C-H···O interactions and π–π stacking interactions [centroid-centroid distance = 3.707 (4)Å symmetry -x,-y,1-z]. (Table1)

Related literature top

For the properties of coumarins, see: Meng et al. (1989); Baures et al. (2002); Jadhav et al. (2010); Gupta et al. (2011); Kokila et al. (1995); Khan et al. (2008). For 4-(bromomethyl)-6-methoxy-2H-chromen-2-one, see: Basanagouda et al. (2011). For [the structure of a?] β-hydroxyethyl side chain containing coumarins, see: Khan et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995). For C—H ···O interactions, see: Desiraju (2005). For stacking interactions, see: Janiak (2000). For related literature [on what subject?], see: Basanagouda & Kulkarni (2011).

Experimental top

The mixture of 4-(bromomethyl)-6-methoxy-2H-chromen-2-one (2.68 g, 0.01 mol) and diethanol amine (1.05 g, 0.015 mol) in a 1:1 (25 ml) mixture of ethylalcohol and ethyl acetate was refluxed for 5-6 h. After completion of the reaction, solvent was removed using rotary evaporator. Obtained viscous mass was diluted with ice cold water and extracted with ethyl acetate and purified by column chromatography using hexane/ ethyl acetate (6:4) as eluting solvent. A slow evaporation technique was used to grow crystals suitable for diffraction studies in ethyl acetate/ hexane (1:1.5) solvent mixture. Light yellow solid; yield 70%; m.p.98-100^oC; IR (KBr, ν in cm^-1) 1716 (C=O), 3319 (OH); ¹H NMR (CDCl₃, 300 MHz, TMS): δ ppm 2.15 (s, br, 1H, OH, D₂O exchangeable), 2.82 (t, 4H, J = 6Hz, 2N-CH₂), 3.34 (s, br, 1H, OH, D₂O exchangeable), 3.69 (t, 4H, J = 6Hz, 2CH₂-OH), 3.86 (s, 3H, C₆-OCH₃), 3.89 (s, 2H, C₄-CH₂), 6.67 (s, 1H, C₃-H), 7.09 (d, 1H, J = 9Hz, Ar-H), 7.23-7.28 (m, 2H, Ar-H). MS m/z (M+1) 294. Anal. Calcd for C₁₅H₁₉NO₅(%):Calcd. C, 61.42; H, 6.53; N, 4.78. Found: C, 61.28; H, 6.39; N, 4.62.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SMART (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. Packing diagram showing intermolecular O—H···O and C—H···O interactions

4-{[Bis(2-hydroxyethyl)amino]methyl}-6-methoxy-2H-chromen-2-one top

Crystal data top

C₁₅H₁₉NO₅	F(000) = 624
M_r = 293.31	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2837 reflections
a = 9.3038 (5) Å	θ = 2.8–29.6°
b = 7.9290 (5) Å	µ = 0.10 mm⁻¹
c = 19.6216 (12) Å	T = 123 K
β = 92.944 (5)°	Block, white
V = 1445.56 (15) Å³	0.2 × 0.18 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX CCD detector diffractometer	1994 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
T_min = 0.98, T_max = 0.982	k = −9→9
14012 measured reflections	l = −23→23
2694 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0607P)² + 0.6914P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2694 reflections	Δρ_max = 0.51 e Å⁻³
194 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (14)

Crystal data top

C₁₅H₁₉NO₅	V = 1445.56 (15) Å³
M_r = 293.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3038 (5) Å	µ = 0.10 mm⁻¹
b = 7.9290 (5) Å	T = 123 K
c = 19.6216 (12) Å	0.2 × 0.18 × 0.18 mm
β = 92.944 (5)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	2694 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1994 reflections with I > 2σ(I)
T_min = 0.98, T_max = 0.982	R_int = 0.040
14012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
2694 reflections	Δρ_min = −0.26 e Å⁻³
194 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6985 (3)	0.3637 (5)	0.38763 (14)	0.0794 (9)
H1A	0.6439	0.2862	0.3572	0.119*
H1B	0.7954	0.3787	0.3713	0.119*
H1C	0.6494	0.473	0.3881	0.119*
C2	0.5821 (2)	0.2628 (3)	0.48505 (12)	0.0478 (6)
C3	0.5966 (3)	0.1769 (3)	0.54703 (13)	0.0576 (7)
H3	0.6895	0.1449	0.5648	0.069*
C4	0.4789 (3)	0.1386 (3)	0.58220 (12)	0.0582 (7)
H4	0.4892	0.0812	0.6247	0.07*
C5	0.3436 (3)	0.1843 (3)	0.55550 (11)	0.0477 (6)
C6	0.0911 (3)	0.1865 (3)	0.57398 (13)	0.0587 (6)
C7	0.0712 (2)	0.2717 (3)	0.50921 (11)	0.0489 (6)
H7	−0.0241	0.2978	0.4929	0.059*
C8	0.1804 (2)	0.3160 (3)	0.47075 (10)	0.0384 (5)
C9	0.3255 (2)	0.2694 (3)	0.49382 (10)	0.0388 (5)
C10	0.4483 (2)	0.3085 (3)	0.45839 (11)	0.0403 (5)
H10	0.4391	0.3666	0.416	0.048*
C11	0.1511 (2)	0.4227 (3)	0.40816 (10)	0.0396 (5)
H11A	0.0465	0.446	0.4035	0.048*
H11B	0.2009	0.5322	0.4151	0.048*
C12	0.1882 (2)	0.4748 (3)	0.28977 (11)	0.0533 (6)
H12A	0.1148	0.5608	0.2994	0.064*
H12B	0.1587	0.419	0.2461	0.064*
C13	0.3309 (3)	0.5588 (3)	0.28329 (13)	0.0631 (7)
H13A	0.3242	0.6448	0.2467	0.076*
H13B	0.3614	0.6154	0.3266	0.076*
C14	0.1223 (2)	0.1916 (3)	0.32783 (12)	0.0512 (6)
H14A	0.0226	0.2163	0.3107	0.061*
H14B	0.1171	0.1226	0.3697	0.061*
C15	0.1966 (3)	0.0928 (4)	0.27525 (14)	0.0663 (7)
H15A	0.159	−0.024	0.2744	0.08*
H15B	0.1741	0.1433	0.2298	0.08*
N1	0.19564 (16)	0.3493 (2)	0.34476 (8)	0.0376 (4)
O1	0.2286 (2)	0.1440 (2)	0.59428 (8)	0.0618 (5)
O2	−0.0017 (2)	0.1540 (3)	0.61251 (10)	0.0857 (7)
O3	0.43185 (19)	0.4325 (3)	0.26743 (10)	0.0751 (6)
H3A	0.506	0.4782	0.2532	0.113*
O4	0.34542 (19)	0.0885 (3)	0.28742 (12)	0.0841 (7)
H4A	0.3776	0.1875	0.2893	0.126*
O5	0.70828 (16)	0.2960 (2)	0.45453 (9)	0.0662 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0469 (14)	0.131 (3)	0.0604 (17)	−0.0038 (16)	0.0068 (12)	−0.0128 (18)
C2	0.0422 (12)	0.0498 (13)	0.0503 (13)	0.0045 (10)	−0.0086 (10)	−0.0120 (11)
C3	0.0588 (15)	0.0521 (14)	0.0592 (15)	0.0117 (12)	−0.0228 (12)	−0.0096 (12)
C4	0.0791 (18)	0.0484 (14)	0.0449 (13)	0.0037 (12)	−0.0171 (12)	0.0041 (11)
C5	0.0628 (14)	0.0406 (12)	0.0396 (12)	−0.0014 (10)	0.0002 (10)	0.0000 (10)
C6	0.0666 (16)	0.0563 (15)	0.0544 (15)	−0.0097 (13)	0.0150 (13)	0.0012 (12)
C7	0.0491 (12)	0.0529 (13)	0.0453 (13)	−0.0036 (10)	0.0101 (10)	−0.0010 (11)
C8	0.0420 (11)	0.0376 (11)	0.0357 (11)	0.0003 (9)	0.0038 (8)	−0.0056 (9)
C9	0.0465 (12)	0.0340 (11)	0.0354 (11)	0.0012 (9)	−0.0014 (9)	−0.0043 (9)
C10	0.0416 (11)	0.0404 (11)	0.0383 (11)	0.0023 (9)	−0.0026 (9)	−0.0053 (9)
C11	0.0349 (10)	0.0443 (12)	0.0400 (11)	0.0048 (9)	0.0040 (8)	−0.0015 (9)
C12	0.0523 (13)	0.0653 (16)	0.0421 (12)	0.0122 (11)	0.0014 (10)	0.0114 (11)
C13	0.0777 (17)	0.0579 (16)	0.0551 (15)	−0.0041 (14)	0.0164 (13)	0.0162 (12)
C14	0.0431 (12)	0.0556 (14)	0.0556 (14)	−0.0050 (10)	0.0102 (10)	−0.0145 (11)
C15	0.0559 (15)	0.0741 (18)	0.0695 (17)	0.0041 (13)	0.0103 (12)	−0.0231 (15)
N1	0.0332 (8)	0.0461 (10)	0.0336 (9)	0.0010 (7)	0.0036 (7)	0.0016 (7)
O1	0.0804 (12)	0.0614 (11)	0.0441 (9)	−0.0060 (9)	0.0082 (8)	0.0127 (8)
O2	0.0929 (14)	0.0930 (16)	0.0747 (13)	−0.0181 (12)	0.0384 (11)	0.0192 (12)
O3	0.0592 (11)	0.0812 (14)	0.0872 (14)	−0.0104 (10)	0.0272 (10)	0.0099 (11)
O4	0.0599 (11)	0.0792 (14)	0.1143 (17)	0.0198 (10)	0.0140 (11)	−0.0294 (13)
O5	0.0376 (9)	0.0929 (14)	0.0672 (12)	0.0067 (9)	−0.0067 (8)	−0.0087 (10)

Geometric parameters (Å, º) top

C1—O5	1.417 (3)	C10—H10	0.95
C1—H1A	0.98	C11—N1	1.453 (2)
C1—H1B	0.98	C11—H11A	0.99
C1—H1C	0.98	C11—H11B	0.99
C2—O5	1.370 (3)	C12—N1	1.467 (3)
C2—C10	1.374 (3)	C12—C13	1.497 (3)
C2—C3	1.394 (3)	C12—H12A	0.99
C3—C4	1.358 (4)	C12—H12B	0.99
C3—H3	0.95	C13—O3	1.419 (3)
C4—C5	1.386 (3)	C13—H13A	0.99
C4—H4	0.95	C13—H13B	0.99
C5—O1	1.382 (3)	C14—N1	1.455 (3)
C5—C9	1.388 (3)	C14—C15	1.493 (3)
C6—O2	1.204 (3)	C14—H14A	0.99
C6—O1	1.363 (3)	C14—H14B	0.99
C6—C7	1.443 (3)	C15—O4	1.393 (3)
C7—C8	1.343 (3)	C15—H15A	0.99
C7—H7	0.95	C15—H15B	0.99
C8—C9	1.450 (3)	O3—H3A	0.84
C8—C11	1.505 (3)	O4—H4A	0.84
C9—C10	1.402 (3)

O5—C1—H1A	109.5	C8—C11—H11A	108.5
O5—C1—H1B	109.5	N1—C11—H11B	108.5
H1A—C1—H1B	109.5	C8—C11—H11B	108.5
O5—C1—H1C	109.5	H11A—C11—H11B	107.5
H1A—C1—H1C	109.5	N1—C12—C13	110.84 (18)
H1B—C1—H1C	109.5	N1—C12—H12A	109.5
O5—C2—C10	124.2 (2)	C13—C12—H12A	109.5
O5—C2—C3	115.36 (19)	N1—C12—H12B	109.5
C10—C2—C3	120.4 (2)	C13—C12—H12B	109.5
C4—C3—C2	120.5 (2)	H12A—C12—H12B	108.1
C4—C3—H3	119.7	O3—C13—C12	107.7 (2)
C2—C3—H3	119.7	O3—C13—H13A	110.2
C3—C4—C5	119.3 (2)	C12—C13—H13A	110.2
C3—C4—H4	120.3	O3—C13—H13B	110.2
C5—C4—H4	120.3	C12—C13—H13B	110.2
O1—C5—C4	116.4 (2)	H13A—C13—H13B	108.5
O1—C5—C9	122.0 (2)	N1—C14—C15	112.37 (19)
C4—C5—C9	121.6 (2)	N1—C14—H14A	109.1
O2—C6—O1	117.1 (2)	C15—C14—H14A	109.1
O2—C6—C7	126.1 (3)	N1—C14—H14B	109.1
O1—C6—C7	116.7 (2)	C15—C14—H14B	109.1
C8—C7—C6	123.4 (2)	H14A—C14—H14B	107.9
C8—C7—H7	118.3	O4—C15—C14	112.7 (2)
C6—C7—H7	118.3	O4—C15—H15A	109.1
C7—C8—C9	118.5 (2)	C14—C15—H15A	109.1
C7—C8—C11	119.67 (19)	O4—C15—H15B	109.1
C9—C8—C11	121.66 (17)	C14—C15—H15B	109.1
C5—C9—C10	118.31 (19)	H15A—C15—H15B	107.8
C5—C9—C8	117.74 (19)	C11—N1—C14	112.88 (16)
C10—C9—C8	123.94 (19)	C11—N1—C12	110.68 (17)
C2—C10—C9	119.9 (2)	C14—N1—C12	114.28 (18)
C2—C10—H10	120.1	C6—O1—C5	121.58 (18)
C9—C10—H10	120.1	C13—O3—H3A	109.5
N1—C11—C8	115.19 (17)	C15—O4—H4A	109.5
N1—C11—H11A	108.5	C2—O5—C1	117.51 (17)

O5—C2—C3—C4	179.4 (2)	C5—C9—C10—C2	0.0 (3)
C10—C2—C3—C4	−0.6 (4)	C8—C9—C10—C2	178.38 (19)
C2—C3—C4—C5	0.7 (4)	C7—C8—C11—N1	−122.5 (2)
C3—C4—C5—O1	−179.1 (2)	C9—C8—C11—N1	62.1 (3)
C3—C4—C5—C9	−0.5 (4)	N1—C12—C13—O3	60.9 (3)
O2—C6—C7—C8	174.7 (3)	N1—C14—C15—O4	43.9 (3)
O1—C6—C7—C8	−3.0 (4)	C8—C11—N1—C14	61.4 (2)
C6—C7—C8—C9	2.9 (3)	C8—C11—N1—C12	−169.10 (17)
C6—C7—C8—C11	−172.6 (2)	C15—C14—N1—C11	−163.4 (2)
O1—C5—C9—C10	178.66 (19)	C15—C14—N1—C12	68.9 (3)
C4—C5—C9—C10	0.1 (3)	C13—C12—N1—C11	94.1 (2)
O1—C5—C9—C8	0.1 (3)	C13—C12—N1—C14	−137.1 (2)
C4—C5—C9—C8	−178.4 (2)	O2—C6—O1—C5	−176.4 (2)
C7—C8—C9—C5	−1.4 (3)	C7—C6—O1—C5	1.6 (3)
C11—C8—C9—C5	174.02 (19)	C4—C5—O1—C6	178.3 (2)
C7—C8—C9—C10	−179.8 (2)	C9—C5—O1—C6	−0.3 (3)
C11—C8—C9—C10	−4.4 (3)	C10—C2—O5—C1	−7.8 (3)
O5—C2—C10—C9	−179.68 (19)	C3—C2—O5—C1	172.2 (2)
C3—C2—C10—C9	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4ⁱ	0.84	1.85	2.685 (3)	174
O4—H4A···O3	0.84	2.06	2.875 (3)	164
C7—H7···O5ⁱⁱ	0.95	2.56	3.494 (2)	167
C14—H14B···O2ⁱⁱⁱ	0.99	2.48	3.206 (3)	130

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₉NO₅
M_r	293.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	9.3038 (5), 7.9290 (5), 19.6216 (12)
β (°)	92.944 (5)
V (Å³)	1445.56 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.2 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.98, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	14012, 2694, 1994
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.149, 1.02
No. of reflections	2694
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.26

Computer programs: SMART (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4ⁱ	0.84	1.85	2.685 (3)	174
O4—H4A···O3	0.84	2.06	2.875 (3)	164
C7—H7···O5ⁱⁱ	0.95	2.56	3.494 (2)	167
C14—H14B···O2ⁱⁱⁱ	0.99	2.48	3.206 (3)	130

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x, −y, −z+1.

Acknowledgements

RJN is grateful to DST, Delhi, India, for providing an INSPIRE fellowship.

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