(4S,5S)-4-Benzyl-2-oxooxazolidine-5-carboxyl­ic acid

In the title compound, C₁₁H₁₁NO₄, the five-membered ring has an envelope conformation. N—H...O and O—H...O hydrogen bonds link the mol­ecules into chains.

Key indicators

• Single-crystal X-ray study
• T = 160 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.027
• wR factor = 0.074
• Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



RADNW_01  Alert C The radiation wavelength lies outside the expected range
          for the supplied radiation type. Expected range 1.54175-1.54180
          Wavelength given =    1.54184

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           67.30
         From the CIF: _reflns_number_total               1851
         Count of symmetry unique reflns         1036
         Completeness (_total/calc)            178.67%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       815
         Fraction of Friedel pairs measured     0.787
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: DIF4 (Stoe & Cie, 1988); cell refinement: DIF4; data reduction: local programs; program(s) used to solve structure: SHELXTL (Sheldrick, 1994); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

(4S,5S)-4-Benzyl-2-oxooxazolidine-5-carboxylic acid

Crystal data

C11H11NO4	F(000) = 232
Mr = 221.21	Dx = 1.411 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 7.244 (3) Å	Cell parameters from 39 reflections
b = 6.3067 (19) Å	θ = 20.6–24.9°
c = 11.554 (3) Å	µ = 0.92 mm^−1
β = 99.41 (3)°	T = 160 K
V = 520.7 (3) Å^3	Block, colourless
Z = 2	0.61 × 0.40 × 0.36 mm

Data collection

Stoe–Siemens four-circle diffractometer	1841 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 67.3°, θmin = 3.9°
ω/θ scans with on–line profile fitting (Clegg, 1981)	h = −8→8
Absorption correction: ψ scan (XPREP in SHELXTL; Sheldrick, 1994)	k = −7→7
Tmin = 0.605, Tmax = 0.720	l = −13→13
2697 measured reflections	5 standard reflections every 60 min
1851 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 0.1206P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.19 e Å^−3
1851 reflections	Δρmin = −0.14 e Å^−3
150 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.044 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 816 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.10 (18)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.46909 (19)	0.9653 (2)	0.87923 (12)	0.0191 (3)
H1	0.4708	1.1232	0.8713	0.023*
O1	0.59408 (12)	0.91003 (18)	0.98597 (8)	0.0214 (3)
C2	0.76640 (18)	0.8784 (2)	0.95726 (12)	0.0194 (3)
N1	0.75525 (16)	0.8763 (2)	0.84128 (10)	0.0204 (3)
H1A	0.843 (3)	0.848 (3)	0.8123 (15)	0.024*
C3	0.56163 (17)	0.8708 (2)	0.77977 (11)	0.0183 (3)
H3	0.5457	0.9685	0.7107	0.022*
O2	0.90231 (13)	0.85652 (19)	1.03383 (8)	0.0259 (3)
C4	0.26896 (17)	0.8996 (2)	0.88681 (12)	0.0192 (3)
O3	0.24353 (13)	0.8680 (2)	0.99507 (8)	0.0233 (2)
H3A	0.1289	0.8509	0.9966	0.028*
O4	0.15062 (13)	0.8926 (2)	0.80017 (8)	0.0276 (3)
C5	0.5001 (2)	0.6452 (2)	0.74110 (12)	0.0208 (3)
H5A	0.5054	0.5534	0.8111	0.025*
H5B	0.3691	0.6480	0.6998	0.025*
C6	0.6248 (2)	0.5547 (2)	0.66082 (12)	0.0196 (3)
C7	0.6263 (2)	0.6411 (2)	0.54973 (12)	0.0215 (3)
H7	0.5461	0.7567	0.5237	0.026*
C8	0.7432 (2)	0.5603 (3)	0.47713 (13)	0.0232 (3)
H8	0.7436	0.6217	0.4021	0.028*
C9	0.8601 (2)	0.3896 (3)	0.51326 (13)	0.0285 (3)
H9	0.9388	0.3329	0.4628	0.034*
C10	0.8608 (2)	0.3032 (3)	0.62325 (15)	0.0316 (4)
H10	0.9404	0.1869	0.6486	0.038*
C11	0.7447 (2)	0.3866 (3)	0.69699 (12)	0.0258 (3)
H11	0.7476	0.3278	0.7730	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0192 (7)	0.0195 (7)	0.0184 (7)	0.0009 (5)	0.0027 (6)	0.0002 (5)
O1	0.0152 (5)	0.0314 (6)	0.0180 (5)	−0.0006 (4)	0.0041 (4)	−0.0014 (4)
C2	0.0164 (6)	0.0196 (7)	0.0231 (7)	−0.0025 (6)	0.0063 (5)	0.0024 (6)
N1	0.0145 (5)	0.0272 (7)	0.0204 (6)	−0.0006 (5)	0.0060 (4)	−0.0025 (5)
C3	0.0163 (6)	0.0215 (7)	0.0177 (6)	0.0012 (5)	0.0045 (5)	0.0008 (6)
O2	0.0161 (5)	0.0392 (7)	0.0223 (5)	−0.0020 (4)	0.0023 (4)	0.0017 (5)
C4	0.0161 (6)	0.0204 (7)	0.0218 (6)	0.0041 (6)	0.0048 (5)	−0.0025 (6)
O3	0.0141 (4)	0.0351 (6)	0.0213 (5)	0.0011 (4)	0.0050 (3)	0.0019 (5)
O4	0.0178 (4)	0.0426 (6)	0.0223 (5)	0.0024 (5)	0.0031 (4)	−0.0023 (5)
C5	0.0207 (7)	0.0217 (7)	0.0208 (6)	−0.0005 (6)	0.0058 (5)	−0.0013 (6)
C6	0.0180 (7)	0.0213 (7)	0.0195 (7)	−0.0028 (6)	0.0034 (5)	−0.0051 (6)
C7	0.0196 (7)	0.0219 (7)	0.0228 (7)	−0.0010 (6)	0.0029 (5)	−0.0010 (6)
C8	0.0225 (7)	0.0271 (7)	0.0204 (7)	−0.0055 (6)	0.0051 (5)	−0.0018 (6)
C9	0.0241 (7)	0.0327 (8)	0.0312 (7)	0.0009 (7)	0.0120 (6)	−0.0040 (7)
C10	0.0289 (8)	0.0307 (9)	0.0364 (9)	0.0120 (7)	0.0087 (7)	0.0041 (7)
C11	0.0283 (7)	0.0261 (8)	0.0235 (7)	0.0021 (7)	0.0061 (5)	0.0037 (7)

Geometric parameters (Å, º)

C1—H1	1.000	C5—H5A	0.990
C1—O1	1.4481 (17)	C5—H5B	0.990
C1—C3	1.5420 (19)	C5—C6	1.509 (2)
C1—C4	1.524 (2)	C6—C7	1.396 (2)
O1—C2	1.3578 (16)	C6—C11	1.391 (2)
C2—N1	1.3293 (19)	C7—H7	0.950
C2—O2	1.2191 (17)	C7—C8	1.383 (2)
N1—H1A	0.785 (19)	C8—H8	0.950
N1—C3	1.4655 (18)	C8—C9	1.391 (2)
C3—H3	1.000	C9—H9	0.950
C3—C5	1.535 (2)	C9—C10	1.382 (2)
C4—O3	1.3090 (17)	C10—H10	0.950
C4—O4	1.2076 (16)	C10—C11	1.394 (2)
O3—H3A	0.840	C11—H11	0.950
H1—C1—O1	107.6	C3—C5—H5B	109.5
H1—C1—C3	107.6	C3—C5—C6	110.78 (12)
H1—C1—C4	107.6	H5A—C5—H5B	108.1
O1—C1—C3	104.71 (11)	H5A—C5—C6	109.5
O1—C1—C4	110.71 (12)	H5B—C5—C6	109.5
C3—C1—C4	118.10 (12)	C5—C6—C7	120.87 (13)
C1—O1—C2	107.41 (10)	C5—C6—C11	120.73 (13)
O1—C2—N1	109.93 (11)	C7—C6—C11	118.38 (14)
O1—C2—O2	120.33 (12)	C6—C7—H7	119.6
N1—C2—O2	129.73 (13)	C6—C7—C8	120.76 (14)
C2—N1—H1A	120.8 (13)	H7—C7—C8	119.6
C2—N1—C3	112.62 (12)	C7—C8—H8	119.8
H1A—N1—C3	124.4 (13)	C7—C8—C9	120.42 (14)
C1—C3—N1	97.33 (11)	H8—C8—C9	119.8
C1—C3—H3	110.4	C8—C9—H9	120.3
C1—C3—C5	115.75 (12)	C8—C9—C10	119.45 (14)
N1—C3—H3	110.4	H9—C9—C10	120.3
N1—C3—C5	111.89 (12)	C9—C10—H10	119.9
H3—C3—C5	110.4	C9—C10—C11	120.10 (15)
C1—C4—O3	112.34 (11)	H10—C10—C11	119.9
C1—C4—O4	121.01 (12)	C6—C11—C10	120.88 (14)
O3—C4—O4	126.50 (12)	C6—C11—H11	119.6
C4—O3—H3A	109.5	C10—C11—H11	119.6
C3—C5—H5A	109.5
C3—C1—O1—C2	23.86 (15)	C3—C1—C4—O3	139.49 (14)
C4—C1—O1—C2	152.17 (12)	C3—C1—C4—O4	−44.6 (2)
C1—O1—C2—N1	−9.54 (16)	C1—C3—C5—C6	−169.25 (11)
C1—O1—C2—O2	170.56 (13)	N1—C3—C5—C6	−58.99 (15)
O1—C2—N1—C3	−10.06 (18)	C3—C5—C6—C7	−66.39 (17)
O2—C2—N1—C3	169.83 (15)	C3—C5—C6—C11	111.94 (15)
C2—N1—C3—C1	23.13 (15)	C5—C6—C7—C8	178.85 (13)
C2—N1—C3—C5	−98.45 (14)	C11—C6—C7—C8	0.5 (2)
O1—C1—C3—N1	−26.95 (13)	C6—C7—C8—C9	0.7 (2)
O1—C1—C3—C5	91.69 (13)	C7—C8—C9—C10	−1.0 (2)
C4—C1—C3—N1	−150.64 (12)	C8—C9—C10—C11	0.1 (2)
C4—C1—C3—C5	−32.01 (17)	C5—C6—C11—C10	−179.71 (14)
O1—C1—C4—O3	18.84 (17)	C7—C6—C11—C10	−1.3 (2)
O1—C1—C4—O4	−165.24 (13)	C9—C10—C11—C6	1.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4^i	0.785 (19)	2.274 (19)	2.9806 (19)	150.1 (18)
O3—H3A···O2^ii	0.84	1.76	2.5841 (16)	165

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