trans-4-(1-Naphth­yl)-2-oxo-1,3-oxazolidine-5-carboxylic acid

Yang, J.-Y.; Ming, Z.-H.; An, J.; Hua, Q.-L.; Lu, L.-Q.

doi:10.1107/S1600536808019132

organic compounds

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Volume 64| Part 8| August 2008| Page o1484

doi:10.1107/S1600536808019132

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trans-4-(1-Naphthyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid

Jiao-Yan Yang,^a Zhi-Hui Ming,^b Jing An,^b Qiu-Lin Hua ^b and Liang-Qiu Lu ^b ^*

^aCollege of Life Sciences, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: luliangqiu@mails.ccnu.edu.cn

(Received 25 May 2008; accepted 24 June 2008; online 12 July 2008)

The crystal structure of the title compound, C₁₄H₁₁NO₄, is influenced by N—H⋯O and O—H⋯O hydrogen bonds, linking molecules into one-dimensional tapes running along the [010] direction.

Related literature

For general backgroud regarding the title compound, see: Lu et al. (2008 ). For patterns in hydrogen bonding, see: Bernstein et al. (1995 ). For related literature, see: Barbachyn & Ford (2003 ); Evans (1982 ); Mukhtar & Wright (2005 ).

Experimental

Crystal data

C₁₄H₁₁NO₄
M_r = 257.24
Orthorhombic, P b c a
a = 8.7159 (17) Å
b = 12.817 (3) Å
c = 20.737 (4) Å
V = 2316.6 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 292 (2) K
0.47 × 0.38 × 0.35 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
12484 measured reflections
2266 independent reflections
2008 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.093
S = 1.04
2266 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 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
O1—H1A⋯O4ⁱ	0.94 (2)	1.72 (2)	2.6591 (15)	174 (2)
N1—H1⋯O2ⁱⁱ	0.834 (17)	2.247 (17)	3.0097 (18)	152.0 (15)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019132/bg2191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808019132/bg2191Isup2.hkl

checkCIF report

Comment top

Oxazolidin-2-ones are prevalent in biologically active molecules (Mukhtar et al., 2005; Barbachyn, et al., 2003), as well as versatile synthons in organic synthesis (Evans, 1982). Recently we reported a new cascade reaction to synthesize these compounds from stable sulfur ylides and nitroolefins (Lu et al., 2008). In order to demostrate the utility of this method we continued to hydrolyze trans-ethyl 4-(naphthalen-1-yl)-2-oxooxazolidine-5-carboxylate with LiOH to obtain trans-4-(naphthalen-1-yl)-2-oxooxazolidine-5-carboxylic acid, and we are presenting herein the X-ray crystallographic analysis of the title compound, thus obtained (Fig. 1),

The crystal structure is determined by N—H···O and O—H···O hydrogen bonds, defining R₂²(8) rings (Bernstein et al. (1995), which link molecules into one-dimensional hydrogen-bonded tapes along [010] ( Fig. 2).

Related literature top

For general backgroud regarding the title compound, see: Lu et al., 2008. For patterns in hydrogen bonding, see: Bernstein et al. (1995). For related literature, see: Barbachyn & Ford (2003); Evans (1982); Mukhtar & Wright (2005).

Experimental top

The starting material, 4-(naphthalen-1-yl)-2-oxooxazolidine-5-carboxylate (100.0 mg, 0.35 mmol) was added to the aqueous solution of LiOH (88.1 mg, 2.10 mmol, 2.5 ml H2O) and the reaction mixture was stirred for 2.5 h. By adjusting the pH = 6–7 with concentrated HCl and 1M diluted HCl solution, the white solid precipitated and was filtrated. The residue was washed with cold water and diethyl ester, the desired product was collected as white power after dryness with 93% yield. Recrystallization from CH3OH—H2O provided the crystalline solid.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of (I) with hydrogen bonds drawn as dashed lines showing the formation of hydrogen-bonded R₂²(8) loops involving NH···O and OH···O hydrogen bonds. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) -x, y - 1/2, -z + 1/2; (ii) -x, y + 1/2, z + 1/2]

trans-4-(1-Naphthyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid top

Crystal data top

C₁₄H₁₁NO₄	F(000) = 1072
M_r = 257.24	D_x = 1.475 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5223 reflections
a = 8.7159 (17) Å	θ = 2.8–28.9°
b = 12.817 (3) Å	µ = 0.11 mm⁻¹
c = 20.737 (4) Å	T = 292 K
V = 2316.6 (8) Å³	Block, colorless
Z = 8	0.47 × 0.38 × 0.35 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2008 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 26.0°, θ_min = 3.0°
ϕ and ω scans	h = −9→10
12484 measured reflections	k = −15→15
2266 independent reflections	l = −25→25

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0416P)² + 0.7823P] where P = (F_o² + 2F_c²)/3
2266 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₄H₁₁NO₄	V = 2316.6 (8) Å³
M_r = 257.24	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.7159 (17) Å	µ = 0.11 mm⁻¹
b = 12.817 (3) Å	T = 292 K
c = 20.737 (4) Å	0.47 × 0.38 × 0.35 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2008 reflections with I > 2σ(I)
12484 measured reflections	R_int = 0.016
2266 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
2266 reflections	Δρ_min = −0.20 e Å⁻³
178 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	0.10060 (15)	0.89669 (10)	0.40612 (6)	0.0322 (3)
C2	0.18399 (17)	0.98662 (11)	0.40013 (7)	0.0415 (3)
H2	0.1971	1.0159	0.3595	0.050*
C3	0.25014 (19)	1.03567 (11)	0.45381 (7)	0.0474 (4)
H3	0.3063	1.0967	0.4484	0.057*
C4	0.23264 (17)	0.99464 (12)	0.51357 (7)	0.0438 (4)
H4	0.2764	1.0280	0.5489	0.053*
C5	0.14847 (15)	0.90147 (11)	0.52271 (6)	0.0363 (3)
C6	0.13034 (17)	0.85684 (12)	0.58449 (7)	0.0435 (4)
H6	0.1731	0.8900	0.6201	0.052*
C7	0.05170 (18)	0.76650 (13)	0.59291 (7)	0.0468 (4)
H7	0.0424	0.7377	0.6339	0.056*
C8	−0.01545 (17)	0.71659 (12)	0.53978 (7)	0.0435 (3)
H8	−0.0694	0.6548	0.5458	0.052*
C9	−0.00239 (15)	0.75784 (10)	0.47936 (6)	0.0359 (3)
H9	−0.0490	0.7242	0.4448	0.043*
C10	0.08091 (14)	0.85104 (10)	0.46843 (6)	0.0315 (3)
C11	0.03291 (15)	0.84401 (10)	0.34692 (6)	0.0326 (3)
H11	−0.0684	0.8149	0.3567	0.039*
C12	0.13968 (15)	0.75872 (10)	0.31821 (6)	0.0356 (3)
H12	0.2150	0.7374	0.3507	0.043*
C13	0.13627 (16)	0.89576 (10)	0.24897 (7)	0.0370 (3)
C14	0.05709 (17)	0.66298 (10)	0.29259 (6)	0.0390 (3)
N1	0.02505 (13)	0.91215 (9)	0.29122 (5)	0.0363 (3)
H1	−0.0281 (18)	0.9662 (13)	0.2897 (7)	0.044*
O1	−0.01994 (14)	0.61525 (9)	0.33777 (5)	0.0538 (3)
H1A	−0.068 (3)	0.5549 (17)	0.3222 (10)	0.081*
O2	0.0653 (2)	0.63355 (10)	0.23870 (5)	0.0869 (5)
O3	0.21709 (11)	0.80945 (7)	0.26568 (5)	0.0429 (3)
O4	0.17042 (13)	0.94603 (8)	0.20100 (5)	0.0497 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0341 (6)	0.0298 (6)	0.0328 (7)	0.0010 (5)	0.0002 (5)	−0.0034 (5)
C2	0.0503 (8)	0.0350 (7)	0.0394 (7)	−0.0056 (6)	0.0002 (6)	0.0012 (6)
C3	0.0529 (9)	0.0346 (8)	0.0545 (9)	−0.0125 (6)	−0.0010 (7)	−0.0056 (6)
C4	0.0452 (8)	0.0422 (8)	0.0439 (8)	−0.0054 (6)	−0.0044 (6)	−0.0138 (6)
C5	0.0358 (7)	0.0378 (7)	0.0353 (7)	0.0037 (6)	−0.0010 (5)	−0.0071 (6)
C6	0.0452 (8)	0.0538 (9)	0.0316 (7)	0.0033 (7)	−0.0036 (6)	−0.0071 (6)
C7	0.0544 (9)	0.0542 (9)	0.0319 (7)	0.0063 (7)	0.0019 (6)	0.0065 (6)
C8	0.0505 (8)	0.0383 (8)	0.0415 (8)	−0.0020 (6)	0.0059 (6)	0.0035 (6)
C9	0.0402 (7)	0.0339 (7)	0.0337 (7)	−0.0017 (6)	0.0008 (5)	−0.0038 (5)
C10	0.0322 (6)	0.0306 (6)	0.0317 (6)	0.0032 (5)	0.0004 (5)	−0.0042 (5)
C11	0.0363 (7)	0.0314 (7)	0.0302 (6)	−0.0008 (5)	−0.0008 (5)	−0.0002 (5)
C12	0.0421 (7)	0.0314 (7)	0.0333 (7)	0.0010 (6)	0.0005 (6)	0.0009 (5)
C13	0.0407 (7)	0.0313 (7)	0.0389 (7)	0.0004 (6)	0.0004 (6)	0.0004 (6)
C14	0.0563 (9)	0.0307 (7)	0.0301 (7)	−0.0004 (6)	0.0037 (6)	−0.0003 (5)
N1	0.0398 (6)	0.0369 (6)	0.0322 (6)	0.0083 (5)	0.0001 (5)	0.0023 (5)
O1	0.0767 (8)	0.0478 (6)	0.0370 (6)	−0.0233 (6)	0.0127 (5)	−0.0085 (5)
O2	0.1626 (15)	0.0612 (8)	0.0371 (6)	−0.0509 (9)	0.0266 (8)	−0.0154 (6)
O3	0.0437 (5)	0.0328 (5)	0.0521 (6)	0.0043 (4)	0.0128 (5)	0.0052 (4)
O4	0.0620 (7)	0.0415 (6)	0.0457 (6)	0.0059 (5)	0.0143 (5)	0.0106 (5)

Geometric parameters (Å, º) top

C1—C2	1.3682 (19)	C8—H8	0.9300
C1—C10	1.4289 (17)	C9—C10	1.4160 (18)
C1—C11	1.5202 (17)	C9—H9	0.9300
C2—C3	1.403 (2)	C11—N1	1.4497 (16)
C2—H2	0.9300	C11—C12	1.5542 (18)
C3—C4	1.355 (2)	C11—H11	0.9800
C3—H3	0.9300	C12—O3	1.4368 (16)
C4—C5	1.414 (2)	C12—C14	1.5185 (19)
C4—H4	0.9300	C12—H12	0.9800
C5—C6	1.4117 (19)	C13—O4	1.2220 (16)
C5—C10	1.4253 (18)	C13—N1	1.3233 (18)
C6—C7	1.357 (2)	C13—O3	1.3565 (16)
C6—H6	0.9300	C14—O2	1.1817 (17)
C7—C8	1.402 (2)	C14—O1	1.3049 (17)
C7—H7	0.9300	N1—H1	0.834 (17)
C8—C9	1.3647 (19)	O1—H1A	0.94 (2)

C2—C1—C10	119.40 (12)	C9—C10—C5	117.90 (12)
C2—C1—C11	120.46 (12)	C9—C10—C1	123.49 (11)
C10—C1—C11	120.12 (11)	C5—C10—C1	118.61 (12)
C1—C2—C3	121.59 (13)	N1—C11—C1	113.21 (11)
C1—C2—H2	119.2	N1—C11—C12	98.44 (10)
C3—C2—H2	119.2	C1—C11—C12	112.92 (11)
C4—C3—C2	120.38 (13)	N1—C11—H11	110.6
C4—C3—H3	119.8	C1—C11—H11	110.6
C2—C3—H3	119.8	C12—C11—H11	110.6
C3—C4—C5	120.58 (13)	O3—C12—C14	108.85 (10)
C3—C4—H4	119.7	O3—C12—C11	104.67 (10)
C5—C4—H4	119.7	C14—C12—C11	114.74 (11)
C6—C5—C4	121.45 (13)	O3—C12—H12	109.5
C6—C5—C10	119.12 (13)	C14—C12—H12	109.5
C4—C5—C10	119.43 (12)	C11—C12—H12	109.5
C7—C6—C5	121.27 (13)	O4—C13—N1	129.31 (13)
C7—C6—H6	119.4	O4—C13—O3	120.76 (12)
C5—C6—H6	119.4	N1—C13—O3	109.92 (12)
C6—C7—C8	119.93 (13)	O2—C14—O1	124.10 (14)
C6—C7—H7	120.0	O2—C14—C12	124.05 (13)
C8—C7—H7	120.0	O1—C14—C12	111.81 (11)
C9—C8—C7	120.66 (14)	C13—N1—C11	113.40 (11)
C9—C8—H8	119.7	C13—N1—H1	120.9 (11)
C7—C8—H8	119.7	C11—N1—H1	123.9 (11)
C8—C9—C10	121.10 (12)	C14—O1—H1A	111.7 (13)
C8—C9—H9	119.5	C13—O3—C12	108.59 (10)
C10—C9—H9	119.5

C10—C1—C2—C3	−0.4 (2)	C2—C1—C11—N1	−17.73 (18)
C11—C1—C2—C3	−178.76 (13)	C10—C1—C11—N1	163.91 (11)
C1—C2—C3—C4	0.0 (2)	C2—C1—C11—C12	93.05 (15)
C2—C3—C4—C5	0.4 (2)	C10—C1—C11—C12	−85.31 (14)
C3—C4—C5—C6	179.30 (15)	N1—C11—C12—O3	21.29 (12)
C3—C4—C5—C10	−0.4 (2)	C1—C11—C12—O3	−98.41 (12)
C4—C5—C6—C7	−178.87 (14)	N1—C11—C12—C14	−97.95 (12)
C10—C5—C6—C7	0.8 (2)	C1—C11—C12—C14	142.36 (11)
C5—C6—C7—C8	−1.0 (2)	O3—C12—C14—O2	4.2 (2)
C6—C7—C8—C9	0.1 (2)	C11—C12—C14—O2	121.12 (18)
C7—C8—C9—C10	0.9 (2)	O3—C12—C14—O1	−177.87 (12)
C8—C9—C10—C5	−1.09 (19)	C11—C12—C14—O1	−61.00 (16)
C8—C9—C10—C1	178.86 (13)	O4—C13—N1—C11	−171.98 (14)
C6—C5—C10—C9	0.22 (19)	O3—C13—N1—C11	7.85 (16)
C4—C5—C10—C9	179.92 (12)	C1—C11—N1—C13	101.23 (13)
C6—C5—C10—C1	−179.73 (12)	C12—C11—N1—C13	−18.24 (14)
C4—C5—C10—C1	−0.03 (19)	O4—C13—O3—C12	−172.25 (13)
C2—C1—C10—C9	−179.53 (13)	N1—C13—O3—C12	7.90 (15)
C11—C1—C10—C9	−1.16 (19)	C14—C12—O3—C13	104.23 (12)
C2—C1—C10—C5	0.42 (19)	C11—C12—O3—C13	−18.91 (13)
C11—C1—C10—C5	178.79 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ⁱ	0.94 (2)	1.72 (2)	2.6591 (15)	174 (2)
N1—H1···O2ⁱⁱ	0.834 (17)	2.247 (17)	3.0097 (18)	152.0 (15)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁NO₄
M_r	257.24
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	8.7159 (17), 12.817 (3), 20.737 (4)
V (Å³)	2316.6 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.47 × 0.38 × 0.35

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12484, 2266, 2008
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.093, 1.05
No. of reflections	2266
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O4ⁱ	0.94 (2)	1.72 (2)	2.6591 (15)	174 (2)
N1—H1···O2ⁱⁱ	0.834 (17)	2.247 (17)	3.0097 (18)	152.0 (15)

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

Acknowledgements

We thank Dr Xiang-Gao Meng for the X-ray data collection.

References

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