Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydro­furan-3-carboxyl­ate

Nirmala, S.; Murugan, R.; Kamala, E.T.S.; Sudha, L.; Narayanan, S.S.

doi:10.1107/S1600536808035988

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2315

doi:10.1107/S1600536808035988

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Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydrofuran-3-carboxylate

S. Nirmala,^a R. Murugan,^b E. Theboral Sugi Kamala,^a L. Sudha ^c ^* and S. Sriman Narayanan ^b

^aDepartment of Physics, Easwari Engineering College, Ramapuram, Chennai 600 089, India, ^bDepartment of Analytical Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India
^*Correspondence e-mail: sudharose18@gmail.com

(Received 19 October 2008; accepted 3 November 2008; online 13 November 2008)

In the title compound, C₂₀H₁₉NO₅, the dihydrofuran ring is almost planar [maximum deviation of 0.021 (2)°] and makes dihedral angles of 28.1 (7) and 54.5 (5)° with the benzyl and phenylamino rings, respectively. The molecular packing is stabilized by intramolecular N—H⋯O hydrogen bonds and intermolecular C—H⋯O interactions.

Related literature

For background on the development of effective and tolerable therapeutic options for cervical cancer, see: Huang et al. (2007 ); Lu et al. (2008 ). For the analysis of apoptosis induced by dihydrofuran carboxylate compounds, see: Chen et al. (2006 ); Lin et al. (2006 ); Zhang & Wei (2007 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Erdsack et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₉NO₅
M_r = 353.36
Triclinic, $[P \overline 1]$
a = 9.1315 (3) Å
b = 10.4040 (3) Å
c = 11.1162 (4) Å
α = 84.848 (2)°
β = 66.436 (2)°
γ = 64.121 (2)°
V = 866.34 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.976, T_max = 0.981
22596 measured reflections
5349 independent reflections
3665 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.163
S = 1.03
5349 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.86	2.12	2.7485 (15)	129
C6—H6⋯O3ⁱ	0.93	2.51	3.3951 (18)	160
C17—H17⋯O4ⁱⁱ	0.93	2.58	3.465 (2)	160
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035988/bq2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808035988/bq2103Isup2.hkl

checkCIF report

Comment top

Human cervical cancer is potentially lethal, and therefore the development of effective and tolerable therapeutic options is vital (Huang et al., 2007; Lu et al., 2008). Dihydrofuran carboxylate compounds induced morphological changes and cytotoxicity in a dose - dependent manner. Dihydrofuran carboxylate compounds induced apoptosis which was analyzed by flow cytometric methods and confirmed by DAPI staining and DNA fragmentation analyzed by DNA gel electrophoresis (Chen et al., 2006; Lin et al., 2006; Zhang & Wei, 2007). In view of this medicinal importance, an X-ray study of the title compound, (I), was carried out.

An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig. 1. The bond lengths in (I) show normal values (Allen et al., 1987) and are comparable to the related structure (Erdsack et al., 2007). The dihydrofuran ring (O2/C1—C4) is planar with a maximum deviation of -0.021 (2)° for C3 from the least square plane defined by all non hydrogen atoms in the molecule. The dihydrofuran ring makes dihedral angles of 28.1 (7)° and 54.5 (5)°, respectively, with the benzyl ring (C12—C17) and phenylamino ring (C5—C10), whereas the benzyl and phenylamino rings are oriented at an angle of 78.6 (6)° with respect to each other.

The crystal structure is stabilized by intramolecular N—H···O interactions. In addition to the van der Waals interactions, the molecular packing in the crystal is also stabilized by intermolecular C—H···O interactions (Table 1, Fig. 2).

Related literature top

For background on the development of effective and tolerable therapeutic options for cervical cancer, see: Huang et al. (2007); Lu et al. (2008). For the analysis of apoptosis induced by dihydrofuran carboxylate compounds, see: Chen et al. (2006); Lin et al. (2006); Zhang & Wei (2007). For bond-length data, see: Allen et al. (1987). For a related structure, see: Erdsack et al. (2007).

Experimental top

1.0 mol of 4-(benzyloxy) aniline (1.0 g) and 1.0 mol of ethyl 2-chloro-4- oxo-4,5-dihydrofuran-3-carboxylate (0.9 g) was allowed to stir in 10 ml of dichloromethane which contains 0.5 ml of triethylamine at room temperature for about 8 hrs. The completion of the reaction was monitored by TLC. After the completion of reaction the crude solid was filtered and then recrystallized in ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids. Dashed line indicates hydrogen bond.
	Fig. 2. The packing of the molecules viewed down the c axis. Dashed lines indicate hydrogen bonds. H atoms not involed in hydrogen bonds have been omitted.

Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydrofuran-3-carboxylate top

Crystal data top

C₂₀H₁₉NO₅	Z = 2
M_r = 353.36	F(000) = 372
Triclinic, P1	D_x = 1.355 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1315 (3) Å	Cell parameters from 6361 reflections
b = 10.4040 (3) Å	θ = 2.6–30.7°
c = 11.1162 (4) Å	µ = 0.10 mm⁻¹
α = 84.848 (2)°	T = 293 K
β = 66.436 (2)°	Prism, yellow
γ = 64.121 (2)°	0.25 × 0.20 × 0.20 mm
V = 866.34 (5) Å³

Data collection top

Bruker Kappa APEXII diffractometer	5349 independent reflections
Radiation source: fine-focus sealed tube	3665 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Bruker axs (kappa apex2) scans	θ_max = 30.7°, θ_min = 2.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −13→13
T_min = 0.976, T_max = 0.981	k = −14→14
22596 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0812P)² + 0.1488P] where P = (F_o² + 2F_c²)/3
5349 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₁₉NO₅	γ = 64.121 (2)°
M_r = 353.36	V = 866.34 (5) Å³
Triclinic, P1	Z = 2
a = 9.1315 (3) Å	Mo Kα radiation
b = 10.4040 (3) Å	µ = 0.10 mm⁻¹
c = 11.1162 (4) Å	T = 293 K
α = 84.848 (2)°	0.25 × 0.20 × 0.20 mm
β = 66.436 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	5349 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3665 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.981	R_int = 0.025
22596 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
5349 reflections	Δρ_min = −0.20 e Å⁻³
235 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	1.26357 (19)	0.57501 (15)	0.0775 (2)	0.0570 (4)
H1A	1.3252	0.5714	0.1323	0.068*
H1B	1.3224	0.6003	−0.0086	0.068*
C2	1.26228 (18)	0.43137 (14)	0.06491 (15)	0.0437 (3)
C3	1.07887 (17)	0.46034 (12)	0.12356 (14)	0.0386 (3)
C4	0.98080 (17)	0.60818 (13)	0.15886 (14)	0.0396 (3)
C5	0.71086 (17)	0.83503 (13)	0.24252 (14)	0.0421 (3)
C6	0.58376 (19)	0.91391 (14)	0.19371 (16)	0.0496 (3)
H6	0.5628	0.8684	0.1383	0.060*
C7	0.4878 (2)	1.06059 (15)	0.22738 (17)	0.0517 (4)
H7	0.4011	1.1138	0.1956	0.062*
C8	0.52074 (18)	1.12851 (14)	0.30861 (15)	0.0447 (3)
C9	0.6476 (2)	1.04905 (15)	0.35756 (16)	0.0515 (4)
H9	0.6699	1.0941	0.4122	0.062*
C10	0.7412 (2)	0.90186 (15)	0.32472 (16)	0.0513 (4)
H10	0.8253	0.8479	0.3587	0.062*
C11	0.4551 (2)	1.34824 (16)	0.41338 (19)	0.0572 (4)
H11A	0.5762	1.3371	0.3698	0.069*
H11B	0.4396	1.3104	0.4983	0.069*
C12	0.3260 (2)	1.50396 (14)	0.43163 (15)	0.0464 (3)
C13	0.1520 (2)	1.54983 (19)	0.51716 (18)	0.0639 (4)
H13	0.1136	1.4836	0.5635	0.077*
C14	0.0329 (3)	1.6920 (2)	0.5359 (2)	0.0798 (6)
H14	−0.0853	1.7216	0.5940	0.096*
C15	0.0884 (3)	1.78924 (19)	0.4692 (3)	0.0816 (7)
H15	0.0083	1.8858	0.4818	0.098*
C16	0.2604 (4)	1.7455 (2)	0.3842 (3)	0.0888 (7)
H16	0.2983	1.8124	0.3390	0.107*
C17	0.3794 (3)	1.6028 (2)	0.3642 (2)	0.0678 (5)
H17	0.4968	1.5734	0.3045	0.081*
C18	0.99189 (18)	0.36906 (13)	0.14162 (14)	0.0416 (3)
C19	1.0226 (3)	0.13250 (17)	0.1330 (3)	0.0729 (6)
H19A	0.9252	0.1571	0.2193	0.088*
H19B	0.9755	0.1409	0.0669	0.088*
C20	1.1542 (3)	−0.01258 (19)	0.1230 (3)	0.0969 (8)
H20A	1.1010	−0.0772	0.1362	0.145*
H20B	1.1996	−0.0205	0.1892	0.145*
H20C	1.2498	−0.0367	0.0372	0.145*
N1	0.80732 (15)	0.68332 (11)	0.20754 (13)	0.0465 (3)
H1	0.7456	0.6366	0.2196	0.056*
O1	0.42051 (15)	1.27356 (10)	0.33465 (12)	0.0582 (3)
O2	1.07889 (13)	0.67841 (9)	0.13778 (12)	0.0516 (3)
O3	1.39676 (13)	0.32190 (11)	0.01100 (13)	0.0599 (3)
O4	0.83217 (13)	0.41370 (11)	0.18030 (13)	0.0568 (3)
O5	1.10361 (13)	0.22984 (10)	0.11310 (12)	0.0522 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0359 (7)	0.0384 (7)	0.0945 (12)	−0.0144 (6)	−0.0230 (7)	−0.0096 (7)
C2	0.0369 (6)	0.0328 (6)	0.0618 (8)	−0.0125 (5)	−0.0221 (6)	−0.0017 (5)
C3	0.0350 (6)	0.0269 (5)	0.0514 (7)	−0.0118 (4)	−0.0164 (5)	0.0010 (5)
C4	0.0365 (6)	0.0293 (5)	0.0512 (7)	−0.0138 (5)	−0.0161 (5)	0.0010 (5)
C5	0.0329 (6)	0.0283 (5)	0.0550 (8)	−0.0099 (5)	−0.0111 (5)	−0.0017 (5)
C6	0.0440 (7)	0.0350 (6)	0.0669 (9)	−0.0108 (6)	−0.0241 (7)	−0.0080 (6)
C7	0.0477 (8)	0.0345 (6)	0.0683 (10)	−0.0062 (6)	−0.0297 (7)	−0.0062 (6)
C8	0.0396 (7)	0.0313 (6)	0.0531 (8)	−0.0074 (5)	−0.0159 (6)	−0.0064 (5)
C9	0.0499 (8)	0.0383 (7)	0.0627 (9)	−0.0108 (6)	−0.0261 (7)	−0.0081 (6)
C10	0.0473 (8)	0.0365 (7)	0.0638 (9)	−0.0073 (6)	−0.0275 (7)	−0.0013 (6)
C11	0.0551 (9)	0.0374 (7)	0.0748 (11)	−0.0102 (6)	−0.0299 (8)	−0.0108 (7)
C12	0.0490 (8)	0.0342 (6)	0.0518 (8)	−0.0126 (6)	−0.0204 (6)	−0.0068 (5)
C13	0.0594 (10)	0.0494 (9)	0.0610 (10)	−0.0147 (8)	−0.0135 (8)	0.0040 (7)
C14	0.0601 (11)	0.0616 (11)	0.0776 (13)	0.0030 (9)	−0.0178 (10)	−0.0184 (10)
C15	0.0951 (16)	0.0345 (8)	0.1246 (18)	−0.0077 (9)	−0.0732 (15)	−0.0061 (10)
C16	0.1034 (18)	0.0548 (11)	0.144 (2)	−0.0476 (12)	−0.0750 (17)	0.0374 (12)
C17	0.0592 (10)	0.0604 (10)	0.0887 (13)	−0.0320 (9)	−0.0288 (10)	0.0112 (9)
C18	0.0398 (7)	0.0289 (5)	0.0547 (8)	−0.0148 (5)	−0.0179 (6)	0.0041 (5)
C19	0.0681 (11)	0.0381 (8)	0.1251 (17)	−0.0328 (8)	−0.0411 (11)	0.0130 (9)
C20	0.0866 (15)	0.0382 (9)	0.163 (3)	−0.0326 (10)	−0.0444 (16)	0.0207 (12)
N1	0.0357 (6)	0.0280 (5)	0.0686 (8)	−0.0124 (4)	−0.0146 (5)	−0.0015 (5)
O1	0.0597 (7)	0.0308 (5)	0.0779 (8)	−0.0033 (4)	−0.0362 (6)	−0.0140 (5)
O2	0.0383 (5)	0.0299 (4)	0.0823 (8)	−0.0144 (4)	−0.0185 (5)	−0.0058 (4)
O3	0.0359 (5)	0.0388 (5)	0.0931 (9)	−0.0083 (4)	−0.0198 (5)	−0.0128 (5)
O4	0.0388 (5)	0.0388 (5)	0.0878 (8)	−0.0184 (4)	−0.0185 (5)	0.0037 (5)
O5	0.0450 (5)	0.0266 (4)	0.0821 (8)	−0.0160 (4)	−0.0215 (5)	0.0018 (4)

Geometric parameters (Å, º) top

C1—O2	1.4466 (17)	C11—H11A	0.9700
C1—C2	1.5190 (19)	C11—H11B	0.9700
C1—H1A	0.9700	C12—C17	1.365 (2)
C1—H1B	0.9700	C12—C13	1.367 (2)
C2—O3	1.2156 (16)	C13—C14	1.373 (2)
C2—C3	1.4291 (19)	C13—H13	0.9300
C3—C4	1.3953 (16)	C14—C15	1.357 (3)
C3—C18	1.4386 (17)	C14—H14	0.9300
C4—N1	1.3126 (17)	C15—C16	1.354 (4)
C4—O2	1.3281 (15)	C15—H15	0.9300
C5—C10	1.371 (2)	C16—C17	1.376 (3)
C5—C6	1.381 (2)	C16—H16	0.9300
C5—N1	1.4287 (15)	C17—H17	0.9300
C6—C7	1.3820 (18)	C18—O4	1.2128 (17)
C6—H6	0.9300	C18—O5	1.3316 (15)
C7—C8	1.387 (2)	C19—C20	1.441 (3)
C7—H7	0.9300	C19—O5	1.4506 (17)
C8—O1	1.3637 (15)	C19—H19A	0.9700
C8—C9	1.381 (2)	C19—H19B	0.9700
C9—C10	1.3847 (19)	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—O1	1.4238 (18)	N1—H1	0.8600
C11—C12	1.5022 (19)

O2—C1—C2	105.83 (11)	C17—C12—C13	118.54 (15)
O2—C1—H1A	110.6	C17—C12—C11	121.00 (15)
C2—C1—H1A	110.6	C13—C12—C11	120.46 (15)
O2—C1—H1B	110.6	C12—C13—C14	121.09 (18)
C2—C1—H1B	110.6	C12—C13—H13	119.5
H1A—C1—H1B	108.7	C14—C13—H13	119.5
O3—C2—C3	131.81 (12)	C15—C14—C13	119.7 (2)
O3—C2—C1	122.98 (13)	C15—C14—H14	120.1
C3—C2—C1	105.18 (11)	C13—C14—H14	120.1
C4—C3—C2	106.96 (11)	C16—C15—C14	119.92 (17)
C4—C3—C18	121.03 (12)	C16—C15—H15	120.0
C2—C3—C18	131.90 (11)	C14—C15—H15	120.0
N1—C4—O2	117.79 (11)	C15—C16—C17	120.4 (2)
N1—C4—C3	127.88 (12)	C15—C16—H16	119.8
O2—C4—C3	114.33 (11)	C17—C16—H16	119.8
C10—C5—C6	120.12 (12)	C12—C17—C16	120.32 (19)
C10—C5—N1	120.95 (13)	C12—C17—H17	119.8
C6—C5—N1	118.92 (13)	C16—C17—H17	119.8
C5—C6—C7	119.82 (13)	O4—C18—O5	122.88 (12)
C5—C6—H6	120.1	O4—C18—C3	123.59 (12)
C7—C6—H6	120.1	O5—C18—C3	113.52 (11)
C6—C7—C8	120.03 (14)	C20—C19—O5	109.29 (15)
C6—C7—H7	120.0	C20—C19—H19A	109.8
C8—C7—H7	120.0	O5—C19—H19A	109.8
O1—C8—C9	124.60 (13)	C20—C19—H19B	109.8
O1—C8—C7	115.48 (13)	O5—C19—H19B	109.8
C9—C8—C7	119.92 (12)	H19A—C19—H19B	108.3
C8—C9—C10	119.57 (14)	C19—C20—H20A	109.5
C8—C9—H9	120.2	C19—C20—H20B	109.5
C10—C9—H9	120.2	H20A—C20—H20B	109.5
C5—C10—C9	120.52 (14)	C19—C20—H20C	109.5
C5—C10—H10	119.7	H20A—C20—H20C	109.5
C9—C10—H10	119.7	H20B—C20—H20C	109.5
O1—C11—C12	107.46 (12)	C4—N1—C5	126.48 (11)
O1—C11—H11A	110.2	C4—N1—H1	116.8
C12—C11—H11A	110.2	C5—N1—H1	116.8
O1—C11—H11B	110.2	C8—O1—C11	117.26 (12)
C12—C11—H11B	110.2	C4—O2—C1	107.56 (10)
H11A—C11—H11B	108.5	C18—O5—C19	115.87 (12)

O2—C1—C2—O3	175.75 (15)	C12—C13—C14—C15	−0.4 (3)
O2—C1—C2—C3	−2.44 (18)	C13—C14—C15—C16	0.3 (3)
O3—C2—C3—C4	−174.22 (17)	C14—C15—C16—C17	0.4 (4)
C1—C2—C3—C4	3.74 (17)	C13—C12—C17—C16	1.0 (3)
O3—C2—C3—C18	1.9 (3)	C11—C12—C17—C16	−178.56 (18)
C1—C2—C3—C18	179.84 (16)	C15—C16—C17—C12	−1.1 (3)
C2—C3—C4—N1	174.99 (15)	C4—C3—C18—O4	4.4 (2)
C18—C3—C4—N1	−1.6 (2)	C2—C3—C18—O4	−171.19 (16)
C2—C3—C4—O2	−4.03 (17)	C4—C3—C18—O5	−174.86 (13)
C18—C3—C4—O2	179.36 (13)	C2—C3—C18—O5	9.5 (2)
C10—C5—C6—C7	0.3 (2)	O2—C4—N1—C5	−0.9 (2)
N1—C5—C6—C7	179.38 (14)	C3—C4—N1—C5	−179.88 (14)
C5—C6—C7—C8	0.8 (2)	C10—C5—N1—C4	−52.3 (2)
C6—C7—C8—O1	179.24 (15)	C6—C5—N1—C4	128.62 (17)
C6—C7—C8—C9	−1.1 (2)	C9—C8—O1—C11	2.8 (2)
O1—C8—C9—C10	179.81 (15)	C7—C8—O1—C11	−177.55 (15)
C7—C8—C9—C10	0.1 (3)	C12—C11—O1—C8	−178.33 (13)
C6—C5—C10—C9	−1.3 (2)	N1—C4—O2—C1	−176.74 (14)
N1—C5—C10—C9	179.71 (14)	C3—C4—O2—C1	2.39 (18)
C8—C9—C10—C5	1.0 (3)	C2—C1—O2—C4	0.15 (18)
O1—C11—C12—C17	−104.90 (19)	O4—C18—O5—C19	−0.9 (2)
O1—C11—C12—C13	75.5 (2)	C3—C18—O5—C19	178.40 (16)
C17—C12—C13—C14	−0.3 (3)	C20—C19—O5—C18	−168.96 (18)
C11—C12—C13—C14	179.31 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.12	2.7485 (15)	129
C6—H6···O3ⁱ	0.93	2.51	3.3951 (18)	160
C17—H17···O4ⁱⁱ	0.93	2.58	3.465 (2)	160

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉NO₅
M_r	353.36
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.1315 (3), 10.4040 (3), 11.1162 (4)
α, β, γ (°)	84.848 (2), 66.436 (2), 64.121 (2)
V (Å³)	866.34 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.976, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	22596, 5349, 3665
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.718

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.163, 1.03
No. of reflections	5349
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.86	2.12	2.7485 (15)	129.4
C6—H6···O3ⁱ	0.93	2.51	3.3951 (18)	160.3
C17—H17···O4ⁱⁱ	0.93	2.58	3.465 (2)	160.2

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

Acknowledgements

SN thanks Professor M. N. Ponnuswamy, Department of Crystallography and Biophysics, University of Madras, India, for his guidance and valuable suggestions, and also the Management of SRM, India, for their support.

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