rac-Ethyl 6-hy­droxy-6-methyl-3-oxo-4-phenyl-1,3,4,5,6,7-hexa­hydro­benzo[c][1,2]oxazole-5-carboxyl­ate

Ismiyev, A.I.; Maharramov, A.M.; Rashidov, B.A.; Mammadova, G.Z.; Askerov, R.K.

doi:10.1107/S1600536811042395

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3018

doi:10.1107/S1600536811042395

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rac-Ethyl 6-hydroxy-6-methyl-3-oxo-4-phenyl-1,3,4,5,6,7-hexahydrobenzo[c][1,2]oxazole-5-carboxylate

Arif I. Ismiyev,^a Abel M. Maharramov,^a ^* Bahruz A. Rashidov,^a Gunay Z. Mammadova ^a and Rizvan K. Askerov ^a

^aBaku State University, Z. Khalilov St. 23, Baku AZ-1148, Azerbaijan
^*Correspondence e-mail: mammadova.87@mail.ru

(Received 1 June 2011; accepted 13 October 2011; online 22 October 2011)

In the title compound, C₁₇H₁₉NO₅, the cyclohexene ring is in a half-chair conformation and the isoxazole ring in an envelope conformation with the N atom as the flap. The C atoms in the 4- and 6-positions are of the same absolute configuration, whereas the C atom in the 5-position is of the opposite configuration, i.e. (4S*,5R*,6S*). The methyl fragment of the ethoxycarbonyl group at position 5 is disordered over two sets of sites in a 0.60:0.40 ratio. The crystal packing displays intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For general background to the synthesis of isoxazoles, see: Kashima et al. (1981 ); Goda et al. (2003 ).

Experimental

Crystal data

C₁₇H₁₉NO₅
M_r = 317.33
Monoclinic, P 2₁
a = 6.0712 (6) Å
b = 13.4343 (13) Å
c = 10.0821 (10) Å
β = 96.882 (2)°
V = 816.39 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.972, T_max = 0.981
9534 measured reflections
4059 independent reflections
2458 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.115
S = 1.00
4059 reflections
218 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6	0.90	1.991	2.846 (3)	159
O6—H6A⋯O3	0.82	1.95	2.767 (3)	171

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811042395/kp2333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042395/kp2333Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042395/kp2333Isup3.cml

checkCIF report

Comment top

The wide range of biological activities of isoxazoles has made them popular synthetic targets. Numerous methods for the synthesis of these heterocycles involve approaches based on either intermolecular cycloaddition of 1,3-dipoles to alkynes or condensations of hydroxylamine with β-diketone equivalent with three carbon 1,3-difunctionalized units bearing sp or sp² carbons, such as propargylic ketones (Kashima et al.1981). Synthesis of isoxazole derivatives has been a subject of consistent interest because of the wide applications of such heterocycles in pharmaceutical and agrochemical industry (Goda et al. 2003). The structure of ethyl-6-hydroxy-6-methyl-3-oxo-4-phenyl-1,3,4,5,6,7- hexahydrobenzo[c]\ isoxazole-5-carboxylate is (I) reported here (Fig. 1). The cyclohexene ring has a half-chair conformation. The phenyl ring is in a pseudo-equatorial position. The torsion angle between the ethoxycarbonyl group and the phenyl substituent C8—C4—C5—C14 is 60.6 (3) which indicates the pseudo-axial location of hydrogen atoms at C4 and C5. The izoxazole ring has an envelope conformation [the torsion angles C7a—N1—O2—C3 is -6.9 (3)° and N1—O2—C3—C3A is 5.2 (3)°]. The title compound (I) is chiral with three stereogenic centres-(4S*,5R*,6S*). The crystal structure involves intermolecular N—H···O and O—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

For general background to the synthesis of isoxazoles, see: Kashima et al. (1981); Goda et al. (2003).

Experimental top

(rac)-Diethyl-4-hydroxy-4-methyl-6-oxo-2-phenyl-1,3-dicarboxylate (20 mmol), hydroxylamine hydrochloride (20 mmol) were dissolved in 20 ml e thanol. Then, 2 drops of H₂SO₄ were added and mixture was stirred at 345–350 K for 10 h. After cooling to a room temperature white crystals were obtained. The crystals were filtered off and washed with ethanol. Then, they were dissolved in ethanol (50 ml)and recrystallized to yield colourless block-shaped crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The hydrogen-bonding (dashed lines) in crystal packing of the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

rac-Ethyl 6-hydroxy-6-methyl-3-oxo-4-phenyl-1,3,4,5,6,7- hexahydrobenzo[c][1,2]oxazole-5-carboxylate top

Crystal data top

C₁₇H₁₉NO₅	F(000) = 336
M_r = 317.33	D_x = 1.291 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1319 reflections
a = 6.0712 (6) Å	θ = 2.5–21.8°
b = 13.4343 (13) Å	µ = 0.10 mm⁻¹
c = 10.0821 (10) Å	T = 296 K
β = 96.882 (2)°	Prism, colourless
V = 816.39 (14) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	4059 independent reflections
Radiation source: fine-focus sealed tube	2458 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
phi and ω scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −8→8
T_min = 0.972, T_max = 0.981	k = −17→17
9534 measured reflections	l = −13→13

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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0469P)²] where P = (F_o² + 2F_c²)/3
4059 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.17 e Å⁻³
3 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₇H₁₉NO₅	V = 816.39 (14) Å³
M_r = 317.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.0712 (6) Å	µ = 0.10 mm⁻¹
b = 13.4343 (13) Å	T = 296 K
c = 10.0821 (10) Å	0.30 × 0.20 × 0.20 mm
β = 96.882 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4059 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2458 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.049
9534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	3 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.17 e Å⁻³
4059 reflections	Δρ_min = −0.15 e Å⁻³
218 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	Occ. (<1)
N1	1.0157 (4)	0.39444 (17)	1.0327 (2)	0.0438 (6)
H1A	1.144 (6)	0.412 (3)	1.008 (4)	0.080 (12)*
O2	1.0458 (3)	0.29676 (15)	1.08762 (19)	0.0483 (5)
O3	0.8411 (3)	0.15884 (16)	1.0854 (2)	0.0596 (6)
O4	0.0789 (3)	0.33341 (17)	0.7160 (2)	0.0632 (6)
O5	0.2738 (4)	0.33256 (18)	0.5417 (2)	0.0645 (6)
O6	0.3701 (3)	0.47677 (14)	0.90741 (18)	0.0455 (5)
H6A	0.3154	0.5327	0.9028	0.068*
C3	0.8575 (4)	0.2429 (2)	1.0425 (3)	0.0407 (7)
C3A	0.7212 (4)	0.30374 (18)	0.9509 (2)	0.0328 (6)
C4	0.5086 (4)	0.27814 (19)	0.8668 (3)	0.0351 (6)
H4A	0.3867	0.2849	0.9217	0.042*
C5	0.4751 (4)	0.35572 (19)	0.7527 (3)	0.0354 (6)
H5A	0.5890	0.3429	0.6937	0.042*
C6	0.5070 (4)	0.46411 (19)	0.8025 (3)	0.0398 (7)
C7	0.7502 (4)	0.4776 (2)	0.8598 (3)	0.0419 (6)
H7A	0.8412	0.4833	0.7874	0.050*
H7B	0.7665	0.5384	0.9119	0.050*
C7A	0.8259 (4)	0.39149 (19)	0.9458 (3)	0.0374 (7)
C8	0.5037 (4)	0.17410 (18)	0.8103 (3)	0.0339 (6)
C9	0.6769 (5)	0.1395 (2)	0.7449 (3)	0.0464 (7)
H9A	0.8001	0.1799	0.7398	0.056*
C10	0.6695 (6)	0.0463 (2)	0.6873 (4)	0.0627 (9)
H10A	0.7857	0.0248	0.6421	0.075*
C11	0.4910 (6)	−0.0146 (2)	0.6965 (3)	0.0619 (9)
H11A	0.4865	−0.0777	0.6584	0.074*
C12	0.3196 (5)	0.0175 (2)	0.7619 (3)	0.0548 (8)
H12A	0.1988	−0.0240	0.7687	0.066*
C13	0.3256 (5)	0.1115 (2)	0.8177 (3)	0.0425 (7)
H13A	0.2074	0.1329	0.8611	0.051*
C14	0.2531 (5)	0.3393 (2)	0.6713 (3)	0.0438 (7)
C15	0.0727 (7)	0.3158 (3)	0.4504 (4)	0.0902 (13)
H15A	0.0826	0.3450	0.3633	0.108*
H15B	−0.0578	0.3412	0.4860	0.108*
C16	0.074 (2)	0.2027 (3)	0.445 (2)	0.110 (4)	0.60
H16A	0.0366	0.1766	0.5284	0.165*	0.60
H16B	0.2192	0.1799	0.4310	0.165*	0.60
H16C	−0.0324	0.1802	0.3736	0.165*	0.60
C16'	−0.009 (4)	0.2095 (5)	0.427 (4)	0.110 (4)	0.40
H16D	0.0820	0.1757	0.3702	0.165*	0.40
H16E	−0.1601	0.2102	0.3862	0.165*	0.40
H16F	−0.0011	0.1753	0.5115	0.165*	0.40
C17	0.4449 (5)	0.5384 (2)	0.6916 (3)	0.0588 (9)
H17A	0.2885	0.5343	0.6630	0.088*
H17B	0.5256	0.5237	0.6176	0.088*
H17C	0.4812	0.6044	0.7237	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0367 (14)	0.0418 (15)	0.0536 (16)	−0.0085 (12)	0.0080 (12)	−0.0056 (12)
O2	0.0403 (10)	0.0500 (13)	0.0525 (12)	−0.0055 (10)	−0.0030 (9)	0.0039 (10)
O3	0.0580 (13)	0.0482 (14)	0.0691 (14)	−0.0091 (10)	−0.0063 (11)	0.0181 (11)
O4	0.0393 (11)	0.0811 (17)	0.0704 (15)	−0.0006 (11)	0.0108 (10)	−0.0120 (13)
O5	0.0652 (13)	0.0827 (17)	0.0436 (12)	−0.0143 (12)	−0.0020 (10)	−0.0021 (12)
O6	0.0438 (10)	0.0340 (10)	0.0620 (13)	0.0023 (9)	0.0194 (10)	−0.0033 (10)
C3	0.0399 (15)	0.0399 (18)	0.0424 (16)	−0.0038 (13)	0.0056 (13)	0.0003 (14)
C3A	0.0347 (13)	0.0279 (13)	0.0367 (14)	−0.0029 (12)	0.0082 (11)	−0.0040 (12)
C4	0.0309 (13)	0.0346 (15)	0.0413 (16)	−0.0029 (11)	0.0100 (12)	−0.0042 (12)
C5	0.0355 (14)	0.0330 (14)	0.0389 (15)	−0.0001 (11)	0.0098 (12)	−0.0003 (11)
C6	0.0436 (15)	0.0329 (15)	0.0450 (17)	−0.0020 (13)	0.0133 (13)	0.0037 (13)
C7	0.0443 (15)	0.0287 (14)	0.0551 (18)	−0.0060 (13)	0.0158 (13)	−0.0020 (13)
C7A	0.0347 (14)	0.0378 (16)	0.0409 (17)	−0.0025 (13)	0.0095 (12)	−0.0096 (13)
C8	0.0325 (14)	0.0347 (15)	0.0340 (15)	−0.0046 (12)	0.0025 (12)	−0.0011 (12)
C9	0.0431 (16)	0.0407 (17)	0.0568 (19)	−0.0052 (13)	0.0119 (15)	−0.0109 (14)
C10	0.061 (2)	0.053 (2)	0.076 (3)	0.0028 (18)	0.0198 (18)	−0.0212 (18)
C11	0.079 (2)	0.0389 (17)	0.066 (2)	−0.0043 (18)	0.0037 (19)	−0.0137 (17)
C12	0.062 (2)	0.0423 (18)	0.060 (2)	−0.0212 (15)	0.0069 (17)	−0.0048 (16)
C13	0.0433 (16)	0.0412 (17)	0.0438 (17)	−0.0043 (13)	0.0083 (13)	−0.0033 (13)
C14	0.0468 (16)	0.0352 (15)	0.0493 (18)	0.0044 (13)	0.0048 (14)	0.0009 (14)
C15	0.095 (3)	0.108 (4)	0.063 (2)	−0.032 (3)	−0.014 (2)	0.002 (2)
C16	0.105 (12)	0.125 (5)	0.087 (7)	−0.055 (4)	−0.043 (9)	−0.008 (4)
C16'	0.105 (12)	0.125 (5)	0.087 (7)	−0.055 (4)	−0.043 (9)	−0.008 (4)
C17	0.067 (2)	0.0434 (18)	0.067 (2)	−0.0003 (15)	0.0113 (17)	0.0132 (16)

Geometric parameters (Å, º) top

N1—C7A	1.361 (3)	C8—C13	1.379 (3)
N1—O2	1.428 (3)	C8—C9	1.387 (4)
N1—H1A	0.88 (3)	C9—C10	1.378 (4)
O2—C3	1.383 (3)	C9—H9A	0.9300
O3—C3	1.218 (3)	C10—C11	1.370 (4)
O4—C14	1.201 (3)	C10—H10A	0.9300
O5—C14	1.330 (3)	C11—C12	1.367 (4)
O5—C15	1.456 (4)	C11—H11A	0.9300
O6—C6	1.432 (3)	C12—C13	1.381 (4)
O6—H6A	0.8200	C12—H12A	0.9300
C3—C3A	1.422 (4)	C13—H13A	0.9300
C3A—C7A	1.343 (3)	C15—C16	1.521 (3)
C3A—C4	1.497 (3)	C15—C16'	1.522 (3)
C4—C8	1.508 (3)	C15—H15A	0.9700
C4—C5	1.548 (3)	C15—H15B	0.9700
C4—H4A	0.9800	C16—H16A	0.9600
C5—C14	1.508 (4)	C16—H16B	0.9600
C5—C6	1.545 (4)	C16—H16C	0.9600
C5—H5A	0.9800	C16'—H16D	0.9600
C6—C17	1.512 (4)	C16'—H16E	0.9600
C6—C7	1.531 (4)	C16'—H16F	0.9600
C7—C7A	1.486 (4)	C17—H17A	0.9600
C7—H7A	0.9700	C17—H17B	0.9600
C7—H7B	0.9700	C17—H17C	0.9600

C7A—N1—O2	106.4 (2)	C10—C9—H9A	119.5
C7A—N1—H1A	123 (2)	C8—C9—H9A	119.5
O2—N1—H1A	107 (2)	C11—C10—C9	120.0 (3)
C3—O2—N1	106.91 (19)	C11—C10—H10A	120.0
C14—O5—C15	117.4 (3)	C9—C10—H10A	120.0
C6—O6—H6A	109.5	C12—C11—C10	119.9 (3)
O3—C3—O2	117.9 (2)	C12—C11—H11A	120.0
O3—C3—C3A	134.3 (3)	C10—C11—H11A	120.0
O2—C3—C3A	107.8 (2)	C11—C12—C13	120.0 (3)
C7A—C3A—C3	106.7 (2)	C11—C12—H12A	120.0
C7A—C3A—C4	124.1 (2)	C13—C12—H12A	120.0
C3—C3A—C4	129.1 (2)	C8—C13—C12	121.2 (3)
C3A—C4—C8	113.8 (2)	C8—C13—H13A	119.4
C3A—C4—C5	107.1 (2)	C12—C13—H13A	119.4
C8—C4—C5	110.4 (2)	O4—C14—O5	123.7 (3)
C3A—C4—H4A	108.5	O4—C14—C5	125.1 (3)
C8—C4—H4A	108.5	O5—C14—C5	111.2 (2)
C5—C4—H4A	108.5	O5—C15—C16	99.6 (4)
C14—C5—C6	112.5 (2)	O5—C15—C16'	118.4 (8)
C14—C5—C4	109.6 (2)	C16—C15—C16'	19.9 (11)
C6—C5—C4	113.2 (2)	O5—C15—H15A	111.8
C14—C5—H5A	107.1	C16—C15—H15A	111.8
C6—C5—H5A	107.1	C16'—C15—H15A	107.2
C4—C5—H5A	107.1	O5—C15—H15B	111.8
O6—C6—C17	110.7 (2)	C16—C15—H15B	111.8
O6—C6—C7	109.0 (2)	C16'—C15—H15B	96.9
C17—C6—C7	110.2 (2)	H15A—C15—H15B	109.6
O6—C6—C5	106.90 (19)	C15—C16—H16A	109.5
C17—C6—C5	111.8 (2)	C15—C16—H16B	109.5
C7—C6—C5	108.2 (2)	C15—C16—H16C	109.5
C7A—C7—C6	110.2 (2)	C15—C16'—H16D	109.5
C7A—C7—H7A	109.6	C15—C16'—H16E	109.5
C6—C7—H7A	109.6	H16D—C16'—H16E	109.5
C7A—C7—H7B	109.6	C15—C16'—H16F	109.5
C6—C7—H7B	109.6	H16D—C16'—H16F	109.5
H7A—C7—H7B	108.1	H16E—C16'—H16F	109.5
C3A—C7A—N1	111.7 (2)	C6—C17—H17A	109.5
C3A—C7A—C7	126.2 (2)	C6—C17—H17B	109.5
N1—C7A—C7	122.1 (2)	H17A—C17—H17B	109.5
C13—C8—C9	117.7 (2)	C6—C17—H17C	109.5
C13—C8—C4	121.6 (2)	H17A—C17—H17C	109.5
C9—C8—C4	120.6 (2)	H17B—C17—H17C	109.5
C10—C9—C8	121.1 (3)

C7A—N1—O2—C3	−6.9 (3)	C3—C3A—C7A—C7	177.7 (2)
N1—O2—C3—O3	−174.8 (2)	C4—C3A—C7A—C7	1.1 (4)
N1—O2—C3—C3A	5.2 (3)	O2—N1—C7A—C3A	6.3 (3)
O3—C3—C3A—C7A	178.5 (3)	O2—N1—C7A—C7	−174.5 (2)
O2—C3—C3A—C7A	−1.4 (3)	C6—C7—C7A—C3A	14.4 (4)
O3—C3—C3A—C4	−5.0 (5)	C6—C7—C7A—N1	−164.6 (2)
O2—C3—C3A—C4	175.0 (2)	C3A—C4—C8—C13	132.5 (3)
C7A—C3A—C4—C8	137.7 (2)	C5—C4—C8—C13	−107.1 (3)
C3—C3A—C4—C8	−38.2 (3)	C3A—C4—C8—C9	−49.6 (3)
C7A—C3A—C4—C5	15.5 (3)	C5—C4—C8—C9	70.8 (3)
C3—C3A—C4—C5	−160.4 (2)	C13—C8—C9—C10	1.1 (4)
C3A—C4—C5—C14	−175.1 (2)	C4—C8—C9—C10	−176.9 (3)
C8—C4—C5—C14	60.6 (3)	C8—C9—C10—C11	−1.4 (5)
C3A—C4—C5—C6	−48.6 (3)	C9—C10—C11—C12	0.6 (5)
C8—C4—C5—C6	−172.89 (19)	C10—C11—C12—C13	0.4 (5)
C14—C5—C6—O6	73.4 (3)	C9—C8—C13—C12	0.0 (4)
C4—C5—C6—O6	−51.5 (3)	C4—C8—C13—C12	177.9 (3)
C14—C5—C6—C17	−47.8 (3)	C11—C12—C13—C8	−0.7 (5)
C4—C5—C6—C17	−172.7 (2)	C15—O5—C14—O4	−0.8 (4)
C14—C5—C6—C7	−169.3 (2)	C15—O5—C14—C5	179.5 (3)
C4—C5—C6—C7	65.8 (3)	C6—C5—C14—O4	−74.8 (3)
O6—C6—C7—C7A	71.3 (3)	C4—C5—C14—O4	52.1 (3)
C17—C6—C7—C7A	−167.1 (2)	C6—C5—C14—O5	104.9 (3)
C5—C6—C7—C7A	−44.6 (3)	C4—C5—C14—O5	−128.2 (2)
C3—C3A—C7A—N1	−3.1 (3)	C14—O5—C15—C16	−91.7 (10)
C4—C3A—C7A—N1	−179.8 (2)	C14—O5—C15—C16'	−84.6 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6	0.897	1.991	2.846 (3)	158.84
O6—H6A···O3	0.82	1.95	2.767 (3)	171

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₅
M_r	317.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.0712 (6), 13.4343 (13), 10.0821 (10)
β (°)	96.882 (2)
V (Å³)	816.39 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.972, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9534, 4059, 2458
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.115, 1.00
No. of reflections	4059
No. of parameters	218
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.15

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6	0.897	1.991	2.846 (3)	158.84
O6—H6A···O3	0.820	1.954	2.767 (3)	170.97

Acknowledgements

We thank Professor Victor N. Khrustalev for fruitful discussions and help in this work.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Goda, F. E., Maroul, A. R. & El-Bendory, E. R. (2003). Saudi Pharm. J. 3, 111–117. Google Scholar
Kashima, C., Yoshihara, N. & Shirai, S. I. (1981). Heterocycles, 16, 145. CrossRef Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3018

doi:10.1107/S1600536811042395

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-Ethyl 6-hy­dr­oxy-6-methyl-3-oxo-4-phenyl-1,3,4,5,6,7-hexa­hydro­benzo[c][1,2]oxazole-5-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-Ethyl 6-hydroxy-6-methyl-3-oxo-4-phenyl-1,3,4,5,6,7-hexahydrobenzo[c][1,2]oxazole-5-carboxylate