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The title compound, C10H11NO3, was synthesized by the reaction of ethyl 3-amin­oxy-2-benzyl-2-hydroxy­propanoate with potassium hydroxide. It was found to crystallize with two independent mol­ecules in the asymmetric unit. In the crystal structure, O—H...O and N—H...O inter­actions link the mol­ecules into one-dimensional chains along the crystallographic a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051816/bh2062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051816/bh2062Isup2.hkl
Contains datablock I

CCDC reference: 633601

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.106
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C2 .. 3.00 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O5 .. C12 .. 3.00 Ang.
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.84 From the CIF: _reflns_number_total 2246 Count of symmetry unique reflns 2268 Completeness (_total/calc) 99.03% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT792_ALERT_1_G Check the Absolute Configuration of C3 = ... S PLAT792_ALERT_1_G Check the Absolute Configuration of C13 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

(4S)-4-Benzyl-4-hydroxyisoxazolidin-3-one top
Crystal data top
C10H11NO3Dx = 1.371 Mg m3
Mr = 193.20Melting point: 421 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3044 reflections
a = 7.8287 (8) Åθ = 2.0–27.8°
b = 7.8026 (8) ŵ = 0.10 mm1
c = 30.6427 (18) ÅT = 113 K
V = 1871.8 (3) Å3Plate, colourless
Z = 80.22 × 0.20 × 0.10 mm
F(000) = 816
Data collection top
Rigaku Saturn
diffractometer
2246 independent reflections
Radiation source: rotating anode2179 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.043
Detector resolution: 7.31 pixels mm-1θmax = 27.8°, θmin = 2.7°
ω scansh = 1010
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 109
Tmin = 0.968, Tmax = 0.990l = 4040
13397 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0563P)2 + 0.3587P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2246 reflectionsΔρmax = 0.30 e Å3
266 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.018 (2)
Special details top

Experimental. IR (KBr pellet, cm-1): 3310m, 3029m, 2759w, 1690 s, 1653w, 1495w, 1460w, 1417w, 1372w, 1320m, 1296w, 1230w, 1142m, 1119w, 1092w, 1033m, 938m, 775m, 730w, 705m, 621w, 585w, 545m.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2845 (3)0.4441 (3)0.11620 (7)0.0204 (4)
H10.379 (4)0.392 (4)0.1169 (12)0.031*
N20.1184 (3)0.4421 (3)0.22242 (7)0.0208 (4)
H20.004 (4)0.389 (4)0.2181 (10)0.031*
O10.1027 (2)0.2155 (2)0.11770 (6)0.0218 (4)
O20.2848 (2)0.6215 (2)0.10854 (6)0.0232 (4)
O30.1284 (3)0.5087 (2)0.13906 (6)0.0204 (4)
H30.211 (5)0.445 (4)0.1319 (12)0.031*
O40.2991 (2)0.2147 (2)0.22006 (6)0.0227 (4)
O50.1185 (2)0.6211 (2)0.23074 (6)0.0227 (4)
O60.5307 (2)0.5085 (2)0.19898 (6)0.0211 (4)
H60.605 (4)0.423 (4)0.2049 (11)0.032*
C10.1325 (3)0.3724 (3)0.11398 (8)0.0177 (5)
C20.1083 (3)0.6741 (3)0.11480 (9)0.0194 (5)
H2A0.07750.76580.09390.023*
H2B0.09080.71740.14480.023*
C30.0006 (3)0.5142 (3)0.10679 (8)0.0180 (5)
C40.0781 (4)0.5002 (3)0.06049 (9)0.0214 (5)
H4A0.14180.39090.05830.026*
H4B0.16100.59470.05640.026*
C50.0523 (3)0.5074 (3)0.02397 (8)0.0225 (5)
C60.0916 (4)0.6620 (4)0.00384 (9)0.0287 (6)
H6A0.03610.76420.01300.034*
C70.2115 (4)0.6681 (4)0.02956 (9)0.0379 (7)
H70.23690.77420.04330.045*
C80.2943 (4)0.5202 (5)0.04293 (10)0.0408 (8)
H80.37690.52490.06560.049*
C90.2554 (4)0.3642 (4)0.02288 (9)0.0362 (7)
H90.31150.26220.03190.043*
C100.1343 (3)0.3591 (4)0.01027 (9)0.0285 (6)
H100.10730.25280.02370.034*
C110.2705 (3)0.3717 (3)0.22407 (8)0.0188 (5)
C120.2951 (3)0.6740 (3)0.22447 (9)0.0204 (5)
H12A0.32670.76400.24580.024*
H12B0.31220.71940.19460.024*
C130.4024 (3)0.5129 (3)0.23158 (8)0.0182 (5)
C140.4818 (3)0.4960 (3)0.27747 (8)0.0216 (5)
H14A0.54430.38580.27910.026*
H14B0.56620.58910.28150.026*
C150.3560 (3)0.5029 (3)0.31448 (9)0.0241 (6)
C160.3167 (4)0.6579 (4)0.33511 (10)0.0349 (7)
H160.37060.76040.32560.042*
C170.2004 (5)0.6641 (5)0.36911 (11)0.0494 (9)
H170.17660.77030.38300.059*
C180.1194 (5)0.5180 (6)0.38285 (11)0.0534 (11)
H180.03870.52350.40600.064*
C190.1543 (4)0.3639 (5)0.36335 (10)0.0480 (9)
H190.09800.26300.37310.058*
C200.2724 (4)0.3547 (4)0.32920 (9)0.0320 (7)
H200.29630.24730.31590.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0163 (10)0.0155 (10)0.0294 (11)0.0016 (8)0.0017 (9)0.0017 (8)
N20.0153 (10)0.0163 (10)0.0309 (11)0.0000 (8)0.0011 (9)0.0006 (9)
O10.0170 (8)0.0177 (8)0.0306 (9)0.0003 (6)0.0010 (7)0.0025 (7)
O20.0151 (9)0.0163 (8)0.0383 (11)0.0012 (7)0.0008 (7)0.0035 (7)
O30.0142 (9)0.0215 (8)0.0254 (8)0.0019 (6)0.0037 (7)0.0010 (7)
O40.0185 (9)0.0180 (8)0.0316 (9)0.0009 (6)0.0015 (7)0.0020 (7)
O50.0130 (9)0.0146 (8)0.0406 (11)0.0007 (6)0.0026 (7)0.0018 (7)
O60.0145 (9)0.0222 (8)0.0266 (9)0.0022 (7)0.0034 (7)0.0020 (7)
C10.0163 (11)0.0194 (11)0.0175 (10)0.0011 (9)0.0012 (9)0.0004 (9)
C20.0128 (11)0.0185 (12)0.0268 (11)0.0002 (9)0.0004 (9)0.0011 (10)
C30.0120 (11)0.0176 (11)0.0245 (11)0.0024 (8)0.0003 (9)0.0005 (8)
C40.0160 (13)0.0225 (11)0.0258 (12)0.0015 (9)0.0018 (9)0.0005 (9)
C50.0164 (13)0.0300 (13)0.0211 (12)0.0014 (10)0.0051 (9)0.0007 (9)
C60.0253 (14)0.0330 (14)0.0279 (13)0.0020 (11)0.0040 (11)0.0018 (11)
C70.0398 (19)0.0477 (18)0.0261 (14)0.0124 (14)0.0008 (12)0.0052 (12)
C80.0313 (17)0.066 (2)0.0247 (14)0.0061 (15)0.0022 (12)0.0020 (13)
C90.0298 (16)0.0521 (19)0.0268 (14)0.0093 (14)0.0012 (12)0.0046 (13)
C100.0272 (14)0.0335 (15)0.0249 (12)0.0044 (11)0.0021 (10)0.0010 (11)
C110.0161 (11)0.0196 (11)0.0206 (10)0.0026 (9)0.0012 (9)0.0004 (9)
C120.0131 (12)0.0208 (12)0.0272 (12)0.0017 (9)0.0026 (10)0.0013 (10)
C130.0144 (12)0.0186 (11)0.0214 (11)0.0002 (9)0.0019 (9)0.0017 (9)
C140.0145 (12)0.0254 (12)0.0248 (12)0.0002 (9)0.0032 (10)0.0020 (9)
C150.0190 (14)0.0319 (13)0.0214 (12)0.0009 (10)0.0023 (10)0.0000 (9)
C160.0389 (17)0.0381 (16)0.0278 (14)0.0050 (13)0.0017 (12)0.0076 (12)
C170.048 (2)0.070 (2)0.0306 (16)0.0204 (19)0.0006 (15)0.0140 (15)
C180.035 (2)0.100 (3)0.0252 (15)0.0057 (19)0.0082 (14)0.0016 (17)
C190.0339 (17)0.082 (3)0.0283 (15)0.0180 (17)0.0036 (13)0.0164 (16)
C200.0260 (15)0.0431 (17)0.0268 (14)0.0094 (12)0.0053 (11)0.0068 (12)
Geometric parameters (Å, º) top
N1—C11.317 (3)C7—C81.385 (5)
N1—O21.404 (3)C7—H70.9500
N1—H10.84 (3)C8—C91.397 (5)
N2—C111.313 (3)C8—H80.9500
N2—O51.420 (3)C9—C101.390 (4)
N2—H20.99 (3)C9—H90.9500
O1—C11.252 (3)C10—H100.9500
O2—C21.454 (3)C11—C131.527 (3)
O3—C31.407 (3)C12—C131.527 (3)
O3—H30.84 (4)C12—H12A0.9900
O4—C111.251 (3)C12—H12B0.9900
O5—C121.456 (3)C13—C141.543 (3)
O6—C131.417 (3)C14—C151.503 (4)
O6—H60.90 (4)C14—H14A0.9900
C1—C31.536 (3)C14—H14B0.9900
C2—C31.531 (3)C15—C161.399 (4)
C2—H2A0.9900C15—C201.403 (4)
C2—H2B0.9900C16—C171.384 (5)
C3—C41.547 (3)C16—H160.9500
C4—C51.516 (4)C17—C181.371 (6)
C4—H4A0.9900C17—H170.9500
C4—H4B0.9900C18—C191.369 (6)
C5—C101.388 (4)C18—H180.9500
C5—C61.389 (4)C19—C201.399 (4)
C6—C71.390 (4)C19—H190.9500
C6—H6A0.9500C20—H200.9500
C1—N1—O2114.3 (2)C10—C9—H9120.2
C1—N1—H1126 (2)C8—C9—H9120.2
O2—N1—H1119 (2)C5—C10—C9120.8 (3)
C11—N2—O5113.8 (2)C5—C10—H10119.6
C11—N2—H2130.3 (17)C9—C10—H10119.6
O5—N2—H2115.8 (17)O4—C11—N2124.6 (2)
N1—O2—C2104.74 (16)O4—C11—C13126.9 (2)
C3—O3—H3112 (2)N2—C11—C13108.5 (2)
N2—O5—C12104.81 (16)O5—C12—C13105.69 (19)
C13—O6—H6109 (2)O5—C12—H12A110.6
O1—C1—N1125.4 (2)C13—C12—H12A110.6
O1—C1—C3126.3 (2)O5—C12—H12B110.6
N1—C1—C3108.3 (2)C13—C12—H12B110.6
O2—C2—C3106.16 (19)H12A—C12—H12B108.7
O2—C2—H2A110.5O6—C13—C12108.02 (19)
C3—C2—H2A110.5O6—C13—C11110.79 (18)
O2—C2—H2B110.5C12—C13—C11101.6 (2)
C3—C2—H2B110.5O6—C13—C14110.8 (2)
H2A—C2—H2B108.7C12—C13—C14115.0 (2)
O3—C3—C2107.97 (19)C11—C13—C14110.4 (2)
O3—C3—C1111.08 (18)C15—C14—C13114.8 (2)
C2—C3—C1100.72 (19)C15—C14—H14A108.6
O3—C3—C4111.3 (2)C13—C14—H14A108.6
C2—C3—C4115.0 (2)C15—C14—H14B108.6
C1—C3—C4110.30 (19)C13—C14—H14B108.6
C5—C4—C3114.2 (2)H14A—C14—H14B107.5
C5—C4—H4A108.7C16—C15—C20117.7 (3)
C3—C4—H4A108.7C16—C15—C14121.1 (2)
C5—C4—H4B108.7C20—C15—C14121.2 (2)
C3—C4—H4B108.7C17—C16—C15121.0 (3)
H4A—C4—H4B107.6C17—C16—H16119.5
C10—C5—C6119.2 (3)C15—C16—H16119.5
C10—C5—C4120.3 (2)C18—C17—C16120.4 (3)
C6—C5—C4120.6 (2)C18—C17—H17119.8
C5—C6—C7120.4 (3)C16—C17—H17119.8
C5—C6—H6A119.8C19—C18—C17120.2 (3)
C7—C6—H6A119.8C19—C18—H18119.9
C8—C7—C6120.4 (3)C17—C18—H18119.9
C8—C7—H7119.8C18—C19—C20120.3 (3)
C6—C7—H7119.8C18—C19—H19119.9
C7—C8—C9119.6 (3)C20—C19—H19119.9
C7—C8—H8120.2C19—C20—C15120.4 (3)
C9—C8—H8120.2C19—C20—H20119.8
C10—C9—C8119.7 (3)C15—C20—H20119.8
C1—N1—O2—C218.2 (3)C8—C9—C10—C50.5 (4)
C11—N2—O5—C1217.9 (3)O5—N2—C11—O4176.1 (2)
O2—N1—C1—O1176.6 (2)O5—N2—C11—C133.9 (3)
O2—N1—C1—C34.2 (3)N2—O5—C12—C1323.6 (2)
N1—O2—C2—C324.0 (2)O5—C12—C13—O6137.6 (2)
O2—C2—C3—O3137.52 (19)O5—C12—C13—C1121.0 (2)
O2—C2—C3—C121.0 (2)O5—C12—C13—C1498.2 (2)
O2—C2—C3—C497.5 (2)O4—C11—C13—O654.6 (3)
O1—C1—C3—O354.3 (3)N2—C11—C13—O6125.4 (2)
N1—C1—C3—O3124.9 (2)O4—C11—C13—C12169.2 (2)
O1—C1—C3—C2168.5 (2)N2—C11—C13—C1210.9 (3)
N1—C1—C3—C210.7 (3)O4—C11—C13—C1468.4 (3)
O1—C1—C3—C469.6 (3)N2—C11—C13—C14111.5 (2)
N1—C1—C3—C4111.2 (2)O6—C13—C14—C15178.80 (19)
O3—C3—C4—C5179.33 (18)C12—C13—C14—C1556.0 (3)
C2—C3—C4—C556.1 (3)C11—C13—C14—C1558.1 (3)
C1—C3—C4—C556.9 (3)C13—C14—C15—C1692.4 (3)
C3—C4—C5—C1086.2 (3)C13—C14—C15—C2086.9 (3)
C3—C4—C5—C693.7 (3)C20—C15—C16—C170.5 (4)
C10—C5—C6—C70.1 (4)C14—C15—C16—C17179.8 (3)
C4—C5—C6—C7179.9 (2)C15—C16—C17—C180.9 (5)
C5—C6—C7—C80.5 (4)C16—C17—C18—C190.8 (5)
C6—C7—C8—C90.5 (5)C17—C18—C19—C200.2 (5)
C7—C8—C9—C100.0 (5)C18—C19—C20—C150.2 (5)
C6—C5—C10—C90.6 (4)C16—C15—C20—C190.0 (4)
C4—C5—C10—C9179.4 (2)C14—C15—C20—C19179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.84 (3)1.94 (3)2.786 (3)176 (3)
O3—H3···O1ii0.84 (4)1.97 (4)2.813 (3)177 (3)
N2—H2···O4ii0.99 (3)1.80 (3)2.784 (3)170 (3)
O6—H6···O4i0.90 (4)1.92 (4)2.805 (3)166 (3)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x1/2, y+1/2, z.
 

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