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The title compound, C11H19NO4, is a precursor for the preparation of (1S,2R,4R)-4-amino-2-(hydroxy­methyl)­cyclo­pentanol, which is an important carbocyclic analogue of β-2-deoxy­ribosyl­amine. The crystal packing of the title compound is stabilized by intermolecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031563/cv6423sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031563/cv6423Isup2.hkl
Contains datablock I

CCDC reference: 262429

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.087
  • Data-to-parameter ratio = 9.1

checkCIF/PLATON results

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Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
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 26.24 From the CIF: _reflns_number_total 1428 Count of symmetry unique reflns 1434 Completeness (_total/calc) 99.58% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2003); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Diamond (Brandenburg, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1S,2R,4R,5R)-tert-Butyl N-(4-hydroxymethyl-6-oxabicyclo[3.1.0]hex-2-yl)carbamate top
Crystal data top
C11H19NO4Dx = 1.245 Mg m3
Mr = 229.27Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 15158 reflections
a = 9.4088 (6) Åθ = 2–26°
b = 10.2617 (8) ŵ = 0.09 mm1
c = 12.6689 (8) ÅT = 193 K
V = 1223.19 (15) Å3Prism, colourless
Z = 40.35 × 0.3 × 0.28 mm
F(000) = 496
Data collection top
Stoe IPDS-II
diffractometer
1256 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 26.2°, θmin = 2.6°
area detector, ω scansh = 1111
17917 measured reflectionsk = 1212
1428 independent reflectionsl = 1515
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0613P)2 + 0.0043P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.032(Δ/σ)max < 0.001
wR(F2) = 0.087Δρmax = 0.17 e Å3
S = 1.06Δρmin = 0.14 e Å3
1428 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
157 parametersExtinction coefficient: 0.051 (8)
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.70776 (17)1.02960 (17)0.37727 (12)0.0445 (4)
O10.50575 (18)1.30213 (14)0.49559 (11)0.0606 (4)
C10.6226 (2)1.2350 (2)0.44583 (15)0.0482 (5)
H10.71491.26950.45640.058*
O20.58230 (16)1.14434 (16)0.19918 (11)0.0539 (4)
C20.60267 (18)1.09014 (19)0.44512 (13)0.0400 (4)
H20.61581.04890.51730.048*
O30.82637 (15)0.91699 (16)0.50292 (10)0.0525 (4)
C30.45105 (19)1.07299 (19)0.40280 (15)0.0435 (4)
H320.38211.06980.46150.052*
H310.44610.98910.36050.052*
O40.89085 (14)0.91190 (15)0.32971 (10)0.0497 (4)
C40.4165 (2)1.1949 (2)0.33648 (15)0.0473 (5)
H40.31341.21960.34530.057*
C50.5128 (3)1.2961 (2)0.38177 (15)0.0540 (5)
H50.5311.3780.34550.065*
C60.4390 (2)1.1787 (2)0.21842 (15)0.0512 (5)
H620.37251.10050.18860.061*
H610.41441.2620.17970.061*
C70.81084 (18)0.95041 (17)0.41163 (13)0.0378 (4)
C81.0166 (2)0.82927 (19)0.34463 (15)0.0442 (4)
C91.1217 (2)0.8950 (3)0.4152 (2)0.0681 (7)
H931.08050.90550.48570.102*
H921.14570.98070.38620.102*
H911.20790.84170.41990.102*
C100.9740 (3)0.6976 (2)0.3869 (3)0.0817 (9)
H1030.93430.70760.45790.123*
H1021.05770.64080.38980.123*
H1010.90240.65880.34030.123*
C111.0738 (3)0.8180 (4)0.2343 (2)0.0912 (11)
H1131.160.76440.23490.137*
H1121.09650.9050.20730.137*
H1111.00220.77720.18890.137*
H100.703 (3)1.043 (2)0.311 (2)0.058 (7)*
H200.598 (3)1.133 (3)0.136 (2)0.072 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0427 (8)0.0580 (9)0.0326 (7)0.0137 (7)0.0028 (6)0.0049 (7)
O10.0857 (11)0.0529 (8)0.0431 (7)0.0100 (8)0.0097 (7)0.0121 (7)
C10.0530 (11)0.0510 (11)0.0407 (9)0.0088 (9)0.0041 (8)0.0090 (8)
O20.0478 (8)0.0800 (10)0.0340 (7)0.0136 (7)0.0007 (6)0.0009 (7)
C20.0396 (9)0.0456 (9)0.0348 (8)0.0038 (8)0.0053 (7)0.0015 (7)
O30.0483 (8)0.0711 (9)0.0380 (6)0.0099 (7)0.0021 (6)0.0137 (7)
C30.0377 (9)0.0452 (10)0.0478 (10)0.0025 (8)0.0076 (7)0.0004 (8)
O40.0503 (8)0.0609 (8)0.0381 (6)0.0229 (7)0.0009 (6)0.0021 (6)
C40.0431 (10)0.0544 (11)0.0445 (10)0.0130 (9)0.0033 (8)0.0014 (8)
C50.0818 (15)0.0393 (9)0.0410 (10)0.0057 (10)0.0086 (10)0.0016 (7)
C60.0487 (11)0.0622 (12)0.0427 (10)0.0140 (9)0.0031 (8)0.0008 (9)
C70.0361 (9)0.0413 (9)0.0362 (8)0.0006 (7)0.0011 (7)0.0039 (7)
C80.0404 (10)0.0449 (10)0.0474 (10)0.0104 (8)0.0017 (8)0.0016 (8)
C90.0381 (10)0.0783 (16)0.0879 (17)0.0037 (11)0.0014 (11)0.0193 (14)
C100.0599 (14)0.0440 (12)0.141 (3)0.0050 (11)0.0007 (15)0.0090 (15)
C110.098 (2)0.121 (2)0.0542 (13)0.067 (2)0.0142 (13)0.0002 (15)
Geometric parameters (Å, º) top
N1—C71.338 (2)C4—C51.493 (3)
N1—C21.450 (2)C4—C61.520 (3)
N1—H100.85 (2)C4—H41.0083
O1—C11.443 (2)C5—H50.9725
O1—C51.445 (2)C6—H621.0853
C1—C51.456 (3)C6—H611.0123
C1—C21.498 (3)C8—C91.494 (3)
C1—H10.9468C8—C111.502 (3)
O2—C61.415 (2)C8—C101.507 (3)
O2—H200.83 (3)C9—H930.98
C2—C31.534 (3)C9—H920.98
C2—H21.0157C9—H910.98
O3—C71.215 (2)C10—H1030.98
C3—C41.542 (3)C10—H1020.98
C3—H320.9875C10—H1010.98
C3—H311.0154C11—H1130.98
O4—C71.342 (2)C11—H1120.98
O4—C81.467 (2)C11—H1110.98
C7—N1—C2124.17 (15)C4—C5—H5121.8
C7—N1—H10117.1 (17)O2—C6—C4109.26 (16)
C2—N1—H10118.7 (17)O2—C6—H62107.8
C1—O1—C560.57 (14)C4—C6—H62110
O1—C1—C559.78 (13)O2—C6—H61110.2
O1—C1—C2112.39 (17)C4—C6—H61110.7
C5—C1—C2109.57 (17)H62—C6—H61108.9
O1—C1—H1117.3O3—C7—N1124.62 (17)
C5—C1—H1124.6O3—C7—O4125.85 (17)
C2—C1—H1119.1N1—C7—O4109.51 (15)
C6—O2—H20112.2 (19)O4—C8—C9110.50 (16)
N1—C2—C1110.06 (16)O4—C8—C11102.34 (16)
N1—C2—C3112.20 (15)C9—C8—C11110.7 (2)
C1—C2—C3103.44 (16)O4—C8—C10110.46 (17)
N1—C2—H2105.8C9—C8—C10111.6 (2)
C1—C2—H2113.1C11—C8—C10110.9 (2)
C3—C2—H2112.4C8—C9—H93109.5
C2—C3—C4107.07 (15)C8—C9—H92109.5
C2—C3—H32110.6H93—C9—H92109.5
C4—C3—H32107.4C8—C9—H91109.5
C2—C3—H31109H93—C9—H91109.5
C4—C3—H31113H92—C9—H91109.5
H32—C3—H31109.8C8—C10—H103109.5
C7—O4—C8121.52 (14)C8—C10—H102109.5
C5—C4—C6111.69 (18)H103—C10—H102109.5
C5—C4—C3103.12 (15)C8—C10—H101109.5
C6—C4—C3114.72 (16)H103—C10—H101109.5
C5—C4—H4111.5H102—C10—H101109.5
C6—C4—H4105.7C8—C11—H113109.5
C3—C4—H4110.2C8—C11—H112109.5
O1—C5—C159.64 (13)H113—C11—H112109.5
O1—C5—C4112.69 (18)C8—C11—H111109.5
C1—C5—C4110.20 (17)H113—C11—H111109.5
O1—C5—H5116.3H112—C11—H111109.5
C1—C5—H5120.7
C5—O1—C1—C2100.33 (19)C2—C1—C5—C40.0 (2)
C7—N1—C2—C1114.1 (2)C6—C4—C5—O1172.90 (17)
C7—N1—C2—C3131.33 (18)C3—C4—C5—O149.2 (2)
O1—C1—C2—N1169.07 (15)C6—C4—C5—C1108.36 (18)
C5—C1—C2—N1104.62 (18)C3—C4—C5—C115.3 (2)
O1—C1—C2—C349.02 (19)C5—C4—C6—O258.3 (2)
C5—C1—C2—C315.44 (19)C3—C4—C6—O258.5 (2)
N1—C2—C3—C493.73 (18)C2—N1—C7—O32.1 (3)
C1—C2—C3—C424.85 (18)C2—N1—C7—O4179.40 (17)
C2—C3—C4—C524.80 (18)C8—O4—C7—O34.6 (3)
C2—C3—C4—C696.9 (2)C8—O4—C7—N1176.95 (16)
C1—O1—C5—C4100.89 (19)C7—O4—C8—C959.4 (2)
C2—C1—C5—O1105.11 (17)C7—O4—C8—C11177.3 (2)
O1—C1—C5—C4105.11 (19)C7—O4—C8—C1064.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H10···O20.85 (2)2.10 (2)2.805 (2)141 (2)
O2—H20···O3i0.83 (3)1.90 (3)2.7050 (18)166 (3)
Symmetry code: (i) x+3/2, y+2, z1/2.
 

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