In the title compound, C
10H
17NO
4, the urethane group is planar and the oxazolidinone ring adopts an envelope conformation. Intermolecular C—H
O interactions link the screw- and glide-related molecules into a two-dimensional network parallel to (101).
Supporting information
CCDC reference: 293858
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.001 Å
- R factor = 0.034
- wR factor = 0.086
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C5 .. 5.52 su
PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C10 .. 2.99 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
tert-Butyl 4,4-dimethyl-5-oxo-1,3-oxazolidine-3-carboxylate
top
Crystal data top
C10H17NO4 | F(000) = 464 |
Mr = 215.25 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2624 reflections |
a = 10.8869 (9) Å | θ = 4.5–27.6° |
b = 6.1138 (5) Å | µ = 0.10 mm−1 |
c = 17.3497 (14) Å | T = 100 K |
β = 90.182 (7)° | Block, colourless |
V = 1154.80 (16) Å3 | 0.45 × 0.30 × 0.26 mm |
Z = 4 | |
Data collection top
Oxford diffraction CCD area-detector diffractometer | 2419 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 27.6°, θmin = 4.5° |
ω scans | h = −13→14 |
8044 measured reflections | k = −7→7 |
2624 independent reflections | l = −22→20 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0384P)2 + 0.3972P] where P = (Fo2 + 2Fc2)/3 |
2624 reflections | (Δ/σ)max = 0.001 |
141 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Special details top
Experimental. N-(tert-butoxycarbonyl)-isobutyryl-5-oxazolidinone |
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 | Uiso*/Ueq | |
C1 | 0.59756 (10) | 1.09731 (18) | 0.63674 (6) | 0.0271 (2) | |
H1A | 0.5204 | 1.1708 | 0.6298 | 0.041* | |
H1B | 0.6480 | 1.1200 | 0.5922 | 0.041* | |
H1C | 0.6384 | 1.1549 | 0.6815 | 0.041* | |
C2 | 0.69576 (10) | 0.7314 (2) | 0.65693 (7) | 0.0296 (2) | |
H2A | 0.6794 | 0.5797 | 0.6668 | 0.044* | |
H2B | 0.7411 | 0.7923 | 0.6994 | 0.044* | |
H2C | 0.7430 | 0.7450 | 0.6106 | 0.044* | |
C3 | 0.49899 (10) | 0.75656 (19) | 0.58294 (6) | 0.0269 (2) | |
H3A | 0.4817 | 0.6060 | 0.5942 | 0.040* | |
H3B | 0.5437 | 0.7661 | 0.5355 | 0.040* | |
H3C | 0.4233 | 0.8360 | 0.5782 | 0.040* | |
C4 | 0.57519 (9) | 0.85370 (16) | 0.64756 (5) | 0.0191 (2) | |
C5 | 0.40752 (8) | 0.90392 (15) | 0.74075 (5) | 0.01702 (19) | |
C6 | 0.43748 (8) | 0.72477 (15) | 0.87205 (5) | 0.01661 (19) | |
C7 | 0.46497 (9) | 0.49095 (16) | 0.84632 (6) | 0.0199 (2) | |
H7A | 0.3924 | 0.4277 | 0.8240 | 0.030* | |
H7B | 0.4902 | 0.4056 | 0.8900 | 0.030* | |
H7C | 0.5296 | 0.4926 | 0.8088 | 0.030* | |
C8 | 0.55246 (9) | 0.83682 (18) | 0.90455 (6) | 0.0248 (2) | |
H8A | 0.5315 | 0.9807 | 0.9224 | 0.037* | |
H8B | 0.6135 | 0.8476 | 0.8649 | 0.037* | |
H8C | 0.5844 | 0.7523 | 0.9467 | 0.037* | |
C9 | 0.33877 (9) | 0.71916 (17) | 0.93418 (6) | 0.0225 (2) | |
C10 | 0.26060 (8) | 0.95188 (16) | 0.84293 (5) | 0.0188 (2) | |
H10A | 0.2660 | 1.1100 | 0.8463 | 0.023* | |
H10B | 0.1923 | 0.9134 | 0.8095 | 0.023* | |
N1 | 0.37501 (7) | 0.85941 (14) | 0.81417 (5) | 0.01758 (18) | |
O1 | 0.51613 (6) | 0.81352 (12) | 0.72316 (4) | 0.02018 (17) | |
O2 | 0.34301 (6) | 1.01302 (12) | 0.69794 (4) | 0.02290 (17) | |
O3 | 0.34010 (8) | 0.61276 (16) | 0.99208 (5) | 0.0374 (2) | |
O4 | 0.24576 (6) | 0.85745 (12) | 0.91756 (4) | 0.02274 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0309 (6) | 0.0250 (5) | 0.0255 (5) | −0.0072 (4) | 0.0019 (4) | 0.0043 (4) |
C2 | 0.0218 (5) | 0.0398 (6) | 0.0272 (5) | 0.0057 (4) | 0.0084 (4) | 0.0090 (5) |
C3 | 0.0267 (5) | 0.0326 (6) | 0.0213 (5) | −0.0062 (4) | 0.0033 (4) | −0.0031 (4) |
C4 | 0.0187 (4) | 0.0233 (5) | 0.0154 (4) | −0.0015 (4) | 0.0049 (3) | 0.0040 (4) |
C5 | 0.0158 (4) | 0.0167 (4) | 0.0186 (4) | −0.0005 (3) | 0.0004 (3) | 0.0016 (3) |
C6 | 0.0158 (4) | 0.0190 (4) | 0.0150 (4) | 0.0017 (3) | 0.0004 (3) | 0.0029 (3) |
C7 | 0.0213 (5) | 0.0185 (5) | 0.0201 (5) | 0.0021 (3) | 0.0002 (3) | 0.0025 (3) |
C8 | 0.0222 (5) | 0.0268 (5) | 0.0252 (5) | −0.0018 (4) | −0.0053 (4) | −0.0001 (4) |
C9 | 0.0218 (5) | 0.0272 (5) | 0.0184 (5) | 0.0044 (4) | 0.0034 (4) | 0.0012 (4) |
C10 | 0.0166 (4) | 0.0188 (4) | 0.0212 (5) | 0.0032 (3) | 0.0035 (3) | 0.0017 (4) |
N1 | 0.0143 (4) | 0.0206 (4) | 0.0178 (4) | 0.0047 (3) | 0.0020 (3) | 0.0037 (3) |
O1 | 0.0175 (3) | 0.0264 (4) | 0.0167 (3) | 0.0053 (3) | 0.0048 (2) | 0.0070 (3) |
O2 | 0.0209 (3) | 0.0258 (4) | 0.0220 (4) | 0.0051 (3) | −0.0011 (3) | 0.0074 (3) |
O3 | 0.0380 (5) | 0.0514 (6) | 0.0227 (4) | 0.0157 (4) | 0.0119 (3) | 0.0151 (4) |
O4 | 0.0208 (3) | 0.0279 (4) | 0.0195 (3) | 0.0056 (3) | 0.0052 (3) | 0.0009 (3) |
Geometric parameters (Å, º) top
C1—C4 | 1.5209 (14) | C6—N1 | 1.4643 (11) |
C1—H1A | 0.96 | C6—C9 | 1.5248 (13) |
C1—H1B | 0.96 | C6—C7 | 1.5275 (13) |
C1—H1C | 0.96 | C6—C8 | 1.5330 (13) |
C2—C4 | 1.5188 (14) | C7—H7A | 0.96 |
C2—H2A | 0.96 | C7—H7B | 0.96 |
C2—H2B | 0.96 | C7—H7C | 0.96 |
C2—H2C | 0.96 | C8—H8A | 0.96 |
C3—C4 | 1.5138 (14) | C8—H8B | 0.96 |
C3—H3A | 0.96 | C8—H8C | 0.96 |
C3—H3B | 0.96 | C9—O3 | 1.197 (1) |
C3—H3C | 0.96 | C9—O4 | 1.350 (1) |
C4—O1 | 1.483 (1) | C10—O4 | 1.4273 (12) |
C5—O2 | 1.219 (1) | C10—N1 | 1.457 (1) |
C5—O1 | 1.341 (1) | C10—H10A | 0.97 |
C5—N1 | 1.351 (1) | C10—H10B | 0.97 |
| | | |
C4—C1—H1A | 109.5 | N1—C6—C8 | 112.21 (8) |
C4—C1—H1B | 109.5 | C9—C6—C8 | 109.06 (8) |
H1A—C1—H1B | 109.5 | C7—C6—C8 | 111.42 (8) |
C4—C1—H1C | 109.5 | C6—C7—H7A | 109.5 |
H1A—C1—H1C | 109.5 | C6—C7—H7B | 109.5 |
H1B—C1—H1C | 109.5 | H7A—C7—H7B | 109.5 |
C4—C2—H2A | 109.5 | C6—C7—H7C | 109.5 |
C4—C2—H2B | 109.5 | H7A—C7—H7C | 109.5 |
H2A—C2—H2B | 109.5 | H7B—C7—H7C | 109.5 |
C4—C2—H2C | 109.5 | C6—C8—H8A | 109.5 |
H2A—C2—H2C | 109.5 | C6—C8—H8B | 109.5 |
H2B—C2—H2C | 109.5 | H8A—C8—H8B | 109.5 |
C4—C3—H3A | 109.5 | C6—C8—H8C | 109.5 |
C4—C3—H3B | 109.5 | H8A—C8—H8C | 109.5 |
H3A—C3—H3B | 109.5 | H8B—C8—H8C | 109.5 |
C4—C3—H3C | 109.5 | O3—C9—O4 | 121.79 (9) |
H3A—C3—H3C | 109.5 | O3—C9—C6 | 126.79 (9) |
H3B—C3—H3C | 109.5 | O4—C9—C6 | 111.40 (8) |
O1—C4—C3 | 110.61 (8) | O4—C10—N1 | 104.66 (7) |
O1—C4—C2 | 101.6 (1) | O4—C10—H10A | 110.8 |
C3—C4—C2 | 110.95 (9) | N1—C10—H10A | 110.8 |
O1—C4—C1 | 109.96 (8) | O4—C10—H10B | 110.8 |
C3—C4—C1 | 112.4 (1) | N1—C10—H10B | 110.8 |
C2—C4—C1 | 110.88 (9) | H10A—C10—H10B | 108.9 |
O2—C5—O1 | 126.40 (9) | C5—N1—C10 | 118.13 (8) |
O2—C5—N1 | 122.17 (9) | C5—N1—C6 | 129.59 (8) |
O1—C5—N1 | 111.4 (1) | C10—N1—C6 | 112.26 (7) |
N1—C6—C9 | 99.82 (7) | C5—O1—C4 | 121.2 (1) |
N1—C6—C7 | 114.63 (8) | C9—O4—C10 | 111.11 (7) |
C9—C6—C7 | 108.95 (8) | | |
| | | |
N1—C6—C9—O3 | 173.07 (11) | C7—C6—N1—C5 | −54.69 (13) |
C7—C6—C9—O3 | 52.63 (14) | C8—C6—N1—C5 | 73.70 (12) |
C8—C6—C9—O3 | −69.18 (14) | C9—C6—N1—C10 | 8.04 (10) |
N1—C6—C9—O4 | −8.46 (10) | C7—C6—N1—C10 | 124.27 (9) |
C7—C6—C9—O4 | −128.90 (9) | C8—C6—N1—C10 | −107.34 (9) |
C8—C6—C9—O4 | 109.30 (9) | O2—C5—O1—C4 | 4.74 (15) |
O2—C5—N1—C10 | −1.95 (14) | N1—C5—O1—C4 | −175.42 (8) |
O1—C5—N1—C10 | 178.20 (8) | C3—C4—O1—C5 | −65.4 (1) |
O2—C5—N1—C6 | 176.96 (9) | C2—C4—O1—C5 | 176.8 (1) |
O1—C5—N1—C6 | −2.9 (1) | C1—C4—O1—C5 | 59.3 (1) |
O4—C10—N1—C5 | 173.91 (8) | O3—C9—O4—C10 | −175.44 (11) |
O4—C10—N1—C6 | −5.19 (10) | C6—C9—O4—C10 | 6.00 (11) |
C9—C6—N1—C5 | −170.92 (10) | N1—C10—O4—C9 | −0.65 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O2 | 0.96 | 2.46 | 3.015 (1) | 116 |
C2—H2C···O3i | 0.96 | 2.47 | 3.404 (2) | 164 |
C3—H3C···O2 | 0.96 | 2.50 | 3.057 (1) | 117 |
C7—H7C···O1 | 0.96 | 2.46 | 2.962 (1) | 112 |
C10—H10B···O2ii | 0.97 | 2.48 | 2.995 (1) | 113 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z+3/2. |