trans-4-(1-Naphth-yl)-2-oxo-1,3-oxazolidine-5-carboxylic acid.

The crystal structure of the title compound, C(14)H(11)NO(4), is influenced by N-H⋯O and O-H⋯O hydrogen bonds, linking mol-ecules 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 = 257.24

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.093

S = 1.04

2266 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H11NO4	F000 = 1072
Mr = 257.24	Dx = 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 = 2.8–28.9º
b = 12.817 (3) Å	µ = 0.11 mm−1
c = 20.737 (4) Å	T = 292 (2) K
V = 2316.6 (8) Å3	Block, colorless
Z = 8	0.47 × 0.38 × 0.35 mm

Bruker SMART 4K CCD area-detector diffractometer	2008 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Monochromator: graphite	θmax = 26.0º
T = 292(2) K	θmin = 3.0º
φ and ω scans	h = −9→10
Absorption correction: none	k = −15→15
12484 measured reflections	l = −25→25
2266 independent reflections

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.7823P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2266 reflections	Δρmax = 0.19 e Å−3
178 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) ; (ii) .