rac-1-(6-Hy­droxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetra­hydro-2,1-benzoxazol-5-yl)ethanone

Maharramov, A.M.; Ismiyev, A.I.; Rashidov, B.A.

doi:10.1107/S1600536810043667

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o3030

https://doi.org/10.1107/S1600536810043667

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rac-1-(6-Hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro-2,1-benzoxazol-5-yl)ethanone

Abel M. Maharramov,^a Arif I. Ismiyev ^a and Bahruz A. Rashidov ^a ^*

^aBaku State University, Z. Khalilov Street 23, Baku AZ-1148, Azerbaijan
^*Correspondence e-mail: Bahruz_81@mail.ru

(Received 8 October 2010; accepted 26 October 2010; online 31 October 2010)

The structure of the title compound, C₁₇H₁₉NO₃, is of interest with respect to antibacterial properties, antibiotic properties and biological activity. The structure displays intermolecular O—H⋯N hydrogen bonding.

Related literature

For general background to Schiff bases and their uses, see: Lau et al. (1999 ); Shawali et al. (1985 ); Raman et al. (2003 ); Yuxia et al. (2002 ).

Experimental

Crystal data

C₁₇H₁₉NO₃
M_r = 285.33
Monoclinic, P 2₁ /c
a = 16.1518 (9) Å
b = 5.5353 (3) Å
c = 17.2956 (9) Å
β = 103.496 (1)°
V = 1503.61 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.09 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 = 0.975, T_max = 0.983
16629 measured reflections
3724 independent reflections
2840 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.141
S = 1.00
3724 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯N1ⁱ	0.82	2.08	2.8689 (17)	162
Symmetry code: (i) -x, -y+2, -z+1.

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: https://doi.org/10.1107/S1600536810043667/pb2043sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043667/pb2043Isup2.hkl

checkCIF report

Comment top

Schiff bases are characterized by the –CH═N– (imine) group which is impotantant in elucidating the mechanism of transamination and racemization reactions in biological systems (Lau et al., 1999; Shawali et al., 1985). Due to the great flexibility and diverse structural aspects, a wide range of Schiff bases have been synthesized and their complexation behaviour studied (Raman et al., 2003). Literature survey shows that Schiff bases show bacteriostatic and bactericidal activity (Yuxia et al., 2002). Antibacterial, antifungal, antitumor, anticancer activity has been reported and they are also active against a wide range of organisms. We have synthesized the title compound, (rac)-5-acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-2H-4,5,6,7-tetrahydrobenzo[c]isoxazole (I), and its structure is reported here. (I) have good antibacterial properties. In the title compound (Fig. 1) all bond lengths and angles are normal. Intermolecular O—H···N hydrogen bonds (Table 1; Fig.2) link molecules into centrosymmetric dimer. The cystal packing is further stablized by van der Waals forces. The two [(C2(R),C4(R)] of three stereogenic centres of tetrahydrobenzo[c]izoxazole moiety are of the same chirality. As the crystal crystallizes in the centrosymmetric space group, the racemate (1:1) is present.

Related literature top

For general background to Schiff bases and their uses, see: Lau et al. (1999); Shawali et al. (1985); Raman et al. (2003); Yuxia et al. (2002).

Experimental top

(rac)-2,4-diacetyl-5-hydroxy-5-methyl-3-phenylcyclohexanon (20 mmol), hydroxylamine hydrochloride (20 mmol) were dissolved in 20 ml ethanol. The mixture was stirred at 345–350 K within 10 h. After cooling to a room temperature obtained white crystals. The crystals was filtered and washed with ethanol. Have been then dissolved in ethanol (50 ml) and recrystallized to yield colourless block-shaped crystals of the title compound.The melting point 140 °C.

Structure description top

For general background to Schiff bases and their uses, see: Lau et al. (1999); Shawali et al. (1985); Raman et al. (2003); Yuxia et al. (2002).

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 were drawn at the 30% probability level.
	Fig. 2. A hydrogen-bonded (dashed lines) ribbon in the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

rac-1-(6-Hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro- 2,1-benzoxazol-5-yl)ethanone top

Crystal data top

C₁₇H₁₉NO₃	F(000) = 608
M_r = 285.33	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5396 reflections
a = 16.1518 (9) Å	θ = 2.4–28.2°
b = 5.5353 (3) Å	µ = 0.09 mm⁻¹
c = 17.2956 (9) Å	T = 296 K
β = 103.496 (1)°	Prism, colourless
V = 1503.61 (14) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3724 independent reflections
Radiation source: fine-focus sealed tube	2840 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −21→21
T_min = 0.975, T_max = 0.983	k = −7→7
16629 measured reflections	l = −23→22

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0748P)² + 0.3882P] where P = (F_o² + 2F_c²)/3
3724 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₉NO₃	V = 1503.61 (14) Å³
M_r = 285.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.1518 (9) Å	µ = 0.09 mm⁻¹
b = 5.5353 (3) Å	T = 296 K
c = 17.2956 (9) Å	0.30 × 0.20 × 0.20 mm
β = 103.496 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3724 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2840 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.021
16629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	Δρ_max = 0.28 e Å⁻³
3724 reflections	Δρ_min = −0.21 e Å⁻³
190 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
N1	0.01908 (8)	1.0929 (3)	0.62899 (8)	0.0564 (4)
O1	0.03792 (7)	0.9296 (3)	0.69321 (7)	0.0604 (3)
C1	0.11922 (9)	0.8524 (3)	0.70211 (9)	0.0487 (4)
C1A	0.15432 (8)	0.9589 (3)	0.64670 (8)	0.0396 (3)
C2	0.24052 (8)	0.9339 (2)	0.62856 (7)	0.0345 (3)
H2A	0.2427	0.7768	0.6030	0.041*
C3	0.25009 (8)	1.1335 (2)	0.56826 (8)	0.0359 (3)
H3A	0.2545	1.2872	0.5970	0.043*
C4	0.16899 (9)	1.1510 (2)	0.49910 (8)	0.0385 (3)
O3	0.14932 (6)	0.90993 (17)	0.47197 (6)	0.0418 (2)
H3B	0.1068	0.9106	0.4352	0.063*
C5	0.09667 (9)	1.2536 (3)	0.53313 (9)	0.0467 (3)
H5A	0.1089	1.4201	0.5492	0.056*
H5B	0.0436	1.2497	0.4928	0.056*
C5A	0.08853 (9)	1.1061 (3)	0.60280 (8)	0.0431 (3)
C6	0.14961 (12)	0.6749 (4)	0.76606 (11)	0.0655 (5)
H6A	0.1053	0.6434	0.7933	0.098*
H6B	0.1986	0.7384	0.8030	0.098*
H6C	0.1647	0.5275	0.7435	0.098*
C7	0.31251 (8)	0.9425 (2)	0.70323 (8)	0.0365 (3)
C8	0.31689 (10)	1.1287 (3)	0.75728 (9)	0.0529 (4)
H8A	0.2767	1.2521	0.7468	0.063*
C9	0.38009 (11)	1.1345 (4)	0.82687 (10)	0.0621 (5)
H9A	0.3818	1.2600	0.8630	0.075*
C10	0.44022 (10)	0.9549 (4)	0.84244 (10)	0.0601 (5)
H10A	0.4823	0.9574	0.8894	0.072*
C11	0.43813 (10)	0.7719 (4)	0.78874 (11)	0.0610 (5)
H11A	0.4796	0.6520	0.7987	0.073*
C12	0.37398 (9)	0.7651 (3)	0.71932 (9)	0.0473 (3)
H12A	0.3726	0.6394	0.6834	0.057*
C13	0.33153 (9)	1.1072 (3)	0.53928 (8)	0.0445 (3)
O2	0.37936 (8)	1.2779 (3)	0.54585 (9)	0.0725 (4)
C14	0.35025 (12)	0.8785 (4)	0.50168 (12)	0.0625 (5)
H14A	0.4038	0.8928	0.4870	0.094*
H14B	0.3060	0.8472	0.4551	0.094*
H14C	0.3530	0.7477	0.5387	0.094*
C15	0.18200 (11)	1.3114 (3)	0.43155 (9)	0.0532 (4)
H15A	0.1305	1.3163	0.3905	0.080*
H15B	0.2273	1.2474	0.4103	0.080*
H15C	0.1964	1.4718	0.4512	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0351 (6)	0.0810 (10)	0.0512 (7)	0.0097 (6)	0.0059 (5)	−0.0093 (7)
O1	0.0367 (6)	0.0925 (9)	0.0544 (6)	0.0057 (6)	0.0159 (5)	0.0004 (6)
C1	0.0355 (7)	0.0662 (10)	0.0456 (8)	0.0015 (7)	0.0119 (6)	−0.0035 (7)
C1A	0.0320 (6)	0.0459 (7)	0.0394 (6)	0.0020 (5)	0.0050 (5)	−0.0050 (6)
C2	0.0307 (6)	0.0357 (6)	0.0359 (6)	0.0021 (5)	0.0054 (5)	−0.0022 (5)
C3	0.0344 (6)	0.0332 (6)	0.0373 (6)	−0.0010 (5)	0.0025 (5)	−0.0031 (5)
C4	0.0373 (6)	0.0355 (7)	0.0386 (6)	0.0015 (5)	0.0005 (5)	−0.0021 (5)
O3	0.0384 (5)	0.0391 (5)	0.0426 (5)	0.0001 (4)	−0.0015 (4)	−0.0072 (4)
C5	0.0412 (7)	0.0453 (8)	0.0479 (8)	0.0106 (6)	−0.0014 (6)	−0.0046 (6)
C5A	0.0326 (6)	0.0512 (8)	0.0422 (7)	0.0062 (6)	0.0018 (5)	−0.0107 (6)
C6	0.0571 (10)	0.0857 (13)	0.0595 (10)	0.0068 (9)	0.0253 (8)	0.0179 (9)
C7	0.0293 (6)	0.0426 (7)	0.0375 (6)	0.0024 (5)	0.0072 (5)	0.0026 (5)
C8	0.0445 (8)	0.0609 (10)	0.0484 (8)	0.0134 (7)	0.0008 (6)	−0.0109 (7)
C9	0.0518 (9)	0.0840 (13)	0.0460 (8)	0.0013 (9)	0.0019 (7)	−0.0165 (8)
C10	0.0404 (8)	0.0890 (13)	0.0451 (8)	−0.0007 (8)	−0.0016 (6)	0.0098 (9)
C11	0.0415 (8)	0.0714 (11)	0.0644 (10)	0.0161 (8)	0.0010 (7)	0.0143 (9)
C12	0.0398 (7)	0.0487 (8)	0.0516 (8)	0.0091 (6)	0.0073 (6)	0.0031 (7)
C13	0.0356 (7)	0.0531 (8)	0.0416 (7)	−0.0058 (6)	0.0028 (5)	0.0071 (6)
O2	0.0510 (7)	0.0752 (9)	0.0902 (9)	−0.0263 (6)	0.0141 (6)	−0.0017 (7)
C14	0.0567 (10)	0.0662 (11)	0.0734 (11)	0.0039 (8)	0.0327 (9)	0.0002 (9)
C15	0.0560 (9)	0.0499 (9)	0.0483 (8)	−0.0014 (7)	0.0013 (7)	0.0101 (7)

Geometric parameters (Å, º) top

N1—C5A	1.306 (2)	C6—H6B	0.9600
N1—O1	1.4090 (19)	C6—H6C	0.9600
O1—C1	1.3550 (18)	C7—C8	1.382 (2)
C1—C1A	1.357 (2)	C7—C12	1.3779 (19)
C1—C6	1.475 (2)	C8—C9	1.385 (2)
C1A—C5A	1.4117 (19)	C8—H8A	0.9300
C1A—C2	1.5032 (18)	C9—C10	1.372 (3)
C2—C7	1.5236 (17)	C9—H9A	0.9300
C2—C3	1.5514 (18)	C10—C11	1.370 (3)
C2—H2A	0.9800	C10—H10A	0.9300
C3—C13	1.520 (2)	C11—C12	1.391 (2)
C3—C4	1.5572 (17)	C11—H11A	0.9300
C3—H3A	0.9800	C12—H12A	0.9300
C4—O3	1.4257 (16)	C13—O2	1.2089 (19)
C4—C15	1.520 (2)	C13—C14	1.486 (2)
C4—C5	1.534 (2)	C14—H14A	0.9600
O3—H3B	0.8200	C14—H14B	0.9600
C5—C5A	1.487 (2)	C14—H14C	0.9600
C5—H5A	0.9700	C15—H15A	0.9600
C5—H5B	0.9700	C15—H15B	0.9600
C6—H6A	0.9600	C15—H15C	0.9600

C5A—N1—O1	105.32 (12)	H6A—C6—H6B	109.5
C1—O1—N1	108.49 (12)	C1—C6—H6C	109.5
O1—C1—C1A	109.66 (14)	H6A—C6—H6C	109.5
O1—C1—C6	116.05 (14)	H6B—C6—H6C	109.5
C1A—C1—C6	134.27 (14)	C8—C7—C12	118.30 (13)
C1—C1A—C5A	104.14 (13)	C8—C7—C2	120.33 (12)
C1—C1A—C2	131.88 (13)	C12—C7—C2	121.36 (12)
C5A—C1A—C2	123.94 (13)	C7—C8—C9	121.07 (15)
C1A—C2—C7	112.40 (11)	C7—C8—H8A	119.5
C1A—C2—C3	108.51 (10)	C9—C8—H8A	119.5
C7—C2—C3	111.81 (10)	C8—C9—C10	119.88 (17)
C1A—C2—H2A	108.0	C8—C9—H9A	120.1
C7—C2—H2A	108.0	C10—C9—H9A	120.1
C3—C2—H2A	108.0	C11—C10—C9	119.92 (14)
C13—C3—C2	112.53 (11)	C11—C10—H10A	120.0
C13—C3—C4	112.97 (11)	C9—C10—H10A	120.0
C2—C3—C4	111.28 (10)	C10—C11—C12	120.04 (15)
C13—C3—H3A	106.5	C10—C11—H11A	120.0
C2—C3—H3A	106.5	C12—C11—H11A	120.0
C4—C3—H3A	106.5	C7—C12—C11	120.76 (15)
O3—C4—C15	110.73 (12)	C7—C12—H12A	119.6
O3—C4—C5	109.96 (12)	C11—C12—H12A	119.6
C15—C4—C5	109.44 (12)	O2—C13—C14	121.07 (15)
O3—C4—C3	106.10 (10)	O2—C13—C3	118.51 (15)
C15—C4—C3	112.61 (12)	C14—C13—C3	120.40 (13)
C5—C4—C3	107.92 (11)	C13—C14—H14A	109.5
C4—O3—H3B	109.5	C13—C14—H14B	109.5
C5A—C5—C4	109.10 (11)	H14A—C14—H14B	109.5
C5A—C5—H5A	109.9	C13—C14—H14C	109.5
C4—C5—H5A	109.9	H14A—C14—H14C	109.5
C5A—C5—H5B	109.9	H14B—C14—H14C	109.5
C4—C5—H5B	109.9	C4—C15—H15A	109.5
H5A—C5—H5B	108.3	C4—C15—H15B	109.5
N1—C5A—C1A	112.39 (14)	H15A—C15—H15B	109.5
N1—C5A—C5	123.88 (13)	C4—C15—H15C	109.5
C1A—C5A—C5	123.71 (13)	H15A—C15—H15C	109.5
C1—C6—H6A	109.5	H15B—C15—H15C	109.5
C1—C6—H6B	109.5

C5A—N1—O1—C1	−0.02 (17)	O1—N1—C5A—C1A	−0.19 (17)
N1—O1—C1—C1A	0.22 (18)	O1—N1—C5A—C5	178.08 (13)
N1—O1—C1—C6	−178.75 (15)	C1—C1A—C5A—N1	0.32 (17)
O1—C1—C1A—C5A	−0.32 (17)	C2—C1A—C5A—N1	178.46 (13)
C6—C1—C1A—C5A	178.4 (2)	C1—C1A—C5A—C5	−177.95 (14)
O1—C1—C1A—C2	−178.25 (14)	C2—C1A—C5A—C5	0.2 (2)
C6—C1—C1A—C2	0.5 (3)	C4—C5—C5A—N1	−157.04 (14)
C1—C1A—C2—C7	−46.1 (2)	C4—C5—C5A—C1A	21.04 (19)
C5A—C1A—C2—C7	136.34 (14)	C1A—C2—C7—C8	−51.35 (18)
C1—C1A—C2—C3	−170.25 (15)	C3—C2—C7—C8	70.98 (16)
C5A—C1A—C2—C3	12.17 (18)	C1A—C2—C7—C12	127.79 (14)
C1A—C2—C3—C13	−173.88 (11)	C3—C2—C7—C12	−109.88 (15)
C7—C2—C3—C13	61.59 (14)	C12—C7—C8—C9	−1.6 (2)
C1A—C2—C3—C4	−45.93 (14)	C2—C7—C8—C9	177.60 (16)
C7—C2—C3—C4	−170.45 (10)	C7—C8—C9—C10	0.8 (3)
C13—C3—C4—O3	79.39 (14)	C8—C9—C10—C11	0.7 (3)
C2—C3—C4—O3	−48.32 (14)	C9—C10—C11—C12	−1.5 (3)
C13—C3—C4—C15	−41.88 (16)	C8—C7—C12—C11	0.8 (2)
C2—C3—C4—C15	−169.60 (12)	C2—C7—C12—C11	−178.33 (14)
C13—C3—C4—C5	−162.78 (12)	C10—C11—C12—C7	0.7 (3)
C2—C3—C4—C5	69.50 (14)	C2—C3—C13—O2	−125.57 (14)
O3—C4—C5—C5A	62.22 (14)	C4—C3—C13—O2	107.38 (16)
C15—C4—C5—C5A	−175.95 (12)	C2—C3—C13—C14	56.16 (17)
C3—C4—C5—C5A	−53.09 (15)	C4—C3—C13—C14	−70.90 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···N1ⁱ	0.82	2.08	2.8689 (17)	162

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₃
M_r	285.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.1518 (9), 5.5353 (3), 17.2956 (9)
β (°)	103.496 (1)
V (Å³)	1503.61 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16629, 3724, 2840
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.141, 1.00
No. of reflections	3724
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

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
O3—H3B···N1ⁱ	0.82000	2.077	2.8689 (17)	162.34

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

The authors 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
Lau, K. Y., Mayr, A. & Cheung, K. K. (1999). Inorg. Chim. Acta, 285, 223–232. Web of Science CSD CrossRef CAS Google Scholar
Raman, N., Muthuraj, V., Ravichandran, S. & Kulandaisamy, A. (2003). Proc. Indian Acad. Sci. 115, 161–167. CrossRef CAS Google Scholar
Shawali, A. S., Harb, N. M. S. & Badahdah, K. O. (1985). J. Heterocycl. Chem. 22, 1397–1403. CrossRef CAS 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
Yuxia, Z., Tao, Z., Wanshan, M., Haibin, Z. & Suifeng, C. (2002). Hauxue Shiji, 24, 117. Google Scholar

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Volume 66| Part 11| November 2010| Page o3030

https://doi.org/10.1107/S1600536810043667

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

rac-1-(6-Hy­dr­oxy-3,6-di­methyl-4-phenyl-4,5,6,7-tetra­hydro-2,1-benzoxazol-5-yl)ethanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-1-(6-Hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro-2,1-benzoxazol-5-yl)ethanone