organic compounds
The title compound, C11H19NO5, is a protected derivative of trans-4-hydroxy-L-proline. The pyrrolidine ring has a twisted conformation. The N atom has planar coordination and is conjugated with the attached ester group. The methyl ester substituent is pseudo-equatorial, while the hydroxy group is pseudo-axial and acts as a hydrogen-bond donor to a carbonyl O atom in an adjacent molecule, forming molecular chains.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026412/bt6386sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026412/bt6386Isup2.hkl |
CCDC reference: 227904
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: local programs; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
1-tert-Butyl 2-methyl
4-(R)-hydroxypyrrolidine-1,2-(2S)-dicarboxylate top
Crystal data top
C11H19NO5 | Dx = 1.293 Mg m−3 |
Mr = 245.27 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 4967 reflections |
a = 9.1813 (10) Å | θ = 2.7–28.9° |
b = 10.7862 (12) Å | µ = 0.10 mm−1 |
c = 12.7242 (14) Å | T = 160 K |
V = 1260.1 (2) Å3 | Plate, colourless |
Z = 4 | 0.53 × 0.24 × 0.09 mm |
F(000) = 528 |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 1486 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 28.9°, θmin = 2.5° |
Detector resolution: 8.192 pixels mm-1 | h = −11→12 |
thin–slice ω scans | k = −10→14 |
7889 measured reflections | l = −16→16 |
1786 independent reflections |
Refinement top
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)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0493P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
1786 reflections | Δρmax = 0.20 e Å−3 |
160 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2001), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (3) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.70934 (13) | 0.42434 (13) | 0.55057 (10) | 0.0226 (3) | |
C2 | 0.85332 (17) | 0.41999 (15) | 0.50152 (12) | 0.0217 (3) | |
H2 | 0.9060 | 0.4994 | 0.5154 | 0.026* | |
C3 | 0.92829 (17) | 0.31374 (15) | 0.56131 (13) | 0.0260 (4) | |
H3A | 0.9083 | 0.2328 | 0.5276 | 0.031* | |
H3B | 1.0349 | 0.3266 | 0.5648 | 0.031* | |
C4 | 0.85984 (18) | 0.32068 (16) | 0.67008 (12) | 0.0266 (4) | |
H4 | 0.8718 | 0.2411 | 0.7095 | 0.032* | |
C5 | 0.69962 (17) | 0.34752 (16) | 0.64609 (13) | 0.0241 (3) | |
H5A | 0.6448 | 0.2701 | 0.6327 | 0.029* | |
H5B | 0.6527 | 0.3934 | 0.7044 | 0.029* | |
C6 | 0.60692 (17) | 0.50151 (15) | 0.51369 (12) | 0.0210 (3) | |
O1 | 0.62695 (12) | 0.56988 (11) | 0.43801 (9) | 0.0263 (3) | |
O2 | 0.48411 (11) | 0.49252 (10) | 0.57003 (9) | 0.0235 (3) | |
C7 | 0.35807 (17) | 0.57536 (16) | 0.54995 (13) | 0.0264 (3) | |
C8 | 0.2575 (2) | 0.5435 (2) | 0.64053 (15) | 0.0386 (5) | |
H8A | 0.2330 | 0.4551 | 0.6378 | 0.058* | |
H8B | 0.1681 | 0.5928 | 0.6351 | 0.058* | |
H8C | 0.3063 | 0.5620 | 0.7072 | 0.058* | |
C9 | 0.28893 (19) | 0.54084 (18) | 0.44555 (14) | 0.0336 (4) | |
H9A | 0.3593 | 0.5542 | 0.3888 | 0.050* | |
H9B | 0.2028 | 0.5926 | 0.4336 | 0.050* | |
H9C | 0.2601 | 0.4534 | 0.4469 | 0.050* | |
C10 | 0.4041 (2) | 0.71036 (17) | 0.55570 (19) | 0.0475 (6) | |
H10A | 0.4578 | 0.7248 | 0.6211 | 0.071* | |
H10B | 0.3175 | 0.7634 | 0.5541 | 0.071* | |
H10C | 0.4667 | 0.7300 | 0.4956 | 0.071* | |
C11 | 0.85210 (18) | 0.39420 (16) | 0.38437 (13) | 0.0244 (3) | |
O3 | 0.94519 (14) | 0.43041 (14) | 0.32595 (10) | 0.0387 (3) | |
O4 | 0.74198 (13) | 0.32101 (11) | 0.35597 (9) | 0.0302 (3) | |
C12 | 0.7372 (2) | 0.2874 (2) | 0.24574 (14) | 0.0399 (5) | |
H12A | 0.7288 | 0.3625 | 0.2029 | 0.060* | |
H12B | 0.6528 | 0.2338 | 0.2329 | 0.060* | |
H12C | 0.8266 | 0.2430 | 0.2269 | 0.060* | |
O5 | 0.92777 (14) | 0.42095 (14) | 0.72302 (9) | 0.0363 (3) | |
H5 | 0.9024 | 0.4208 | 0.7865 | 0.055* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0206 (6) | 0.0283 (7) | 0.0189 (6) | 0.0039 (6) | 0.0035 (5) | 0.0025 (6) |
C2 | 0.0180 (7) | 0.0253 (8) | 0.0218 (7) | 0.0008 (7) | 0.0018 (6) | −0.0009 (7) |
C3 | 0.0225 (7) | 0.0297 (9) | 0.0258 (8) | 0.0043 (7) | −0.0012 (7) | 0.0012 (7) |
C4 | 0.0257 (8) | 0.0311 (9) | 0.0230 (8) | 0.0018 (7) | −0.0009 (7) | 0.0050 (7) |
C5 | 0.0231 (7) | 0.0270 (8) | 0.0223 (8) | 0.0009 (7) | 0.0002 (6) | 0.0051 (7) |
C6 | 0.0210 (7) | 0.0228 (7) | 0.0191 (7) | −0.0017 (6) | −0.0013 (6) | −0.0038 (6) |
O1 | 0.0259 (6) | 0.0290 (6) | 0.0240 (5) | −0.0006 (5) | −0.0005 (5) | 0.0058 (5) |
O2 | 0.0186 (5) | 0.0284 (6) | 0.0235 (6) | 0.0041 (5) | 0.0010 (5) | 0.0028 (5) |
C7 | 0.0185 (7) | 0.0279 (8) | 0.0329 (9) | 0.0044 (7) | −0.0020 (7) | 0.0003 (8) |
C8 | 0.0262 (8) | 0.0549 (12) | 0.0345 (9) | 0.0085 (9) | 0.0029 (8) | −0.0035 (9) |
C9 | 0.0276 (8) | 0.0414 (10) | 0.0317 (9) | 0.0025 (8) | −0.0059 (7) | 0.0048 (8) |
C10 | 0.0331 (10) | 0.0274 (10) | 0.0821 (16) | 0.0038 (8) | −0.0010 (11) | −0.0077 (11) |
C11 | 0.0212 (8) | 0.0264 (8) | 0.0256 (8) | 0.0021 (7) | 0.0022 (6) | 0.0030 (6) |
O3 | 0.0313 (6) | 0.0574 (9) | 0.0272 (6) | −0.0105 (7) | 0.0078 (5) | 0.0027 (7) |
O4 | 0.0330 (6) | 0.0348 (7) | 0.0229 (6) | −0.0073 (6) | 0.0045 (5) | −0.0048 (5) |
C12 | 0.0504 (11) | 0.0454 (11) | 0.0238 (9) | −0.0121 (10) | 0.0041 (8) | −0.0096 (8) |
O5 | 0.0312 (7) | 0.0560 (9) | 0.0218 (6) | −0.0069 (7) | −0.0012 (5) | −0.0039 (6) |
Geometric parameters (Å, º) top
N1—C2 | 1.463 (2) | C7—C9 | 1.519 (2) |
N1—C5 | 1.4738 (19) | C7—C10 | 1.518 (3) |
N1—C6 | 1.341 (2) | C8—H8A | 0.980 |
C2—H2 | 1.000 | C8—H8B | 0.980 |
C2—C3 | 1.538 (2) | C8—H8C | 0.980 |
C2—C11 | 1.516 (2) | C9—H9A | 0.980 |
C3—H3A | 0.990 | C9—H9B | 0.980 |
C3—H3B | 0.990 | C9—H9C | 0.980 |
C3—C4 | 1.522 (2) | C10—H10A | 0.980 |
C4—H4 | 1.000 | C10—H10B | 0.980 |
C4—C5 | 1.530 (2) | C10—H10C | 0.980 |
C4—O5 | 1.419 (2) | C11—O3 | 1.198 (2) |
C5—H5A | 0.990 | C11—O4 | 1.333 (2) |
C5—H5B | 0.990 | O4—C12 | 1.450 (2) |
C6—O1 | 1.2267 (19) | C12—H12A | 0.980 |
C6—O2 | 1.3397 (19) | C12—H12B | 0.980 |
O2—C7 | 1.4842 (19) | C12—H12C | 0.980 |
C7—C8 | 1.516 (2) | O5—H5 | 0.840 |
C2—N1—C5 | 112.86 (12) | O2—C7—C10 | 110.62 (13) |
C2—N1—C6 | 120.30 (13) | C8—C7—C9 | 110.77 (15) |
C5—N1—C6 | 126.54 (13) | C8—C7—C10 | 110.51 (16) |
N1—C2—H2 | 109.5 | C9—C7—C10 | 113.19 (16) |
N1—C2—C3 | 102.55 (12) | C7—C8—H8A | 109.5 |
N1—C2—C11 | 114.75 (13) | C7—C8—H8B | 109.5 |
H2—C2—C3 | 109.5 | C7—C8—H8C | 109.5 |
H2—C2—C11 | 109.5 | H8A—C8—H8B | 109.5 |
C3—C2—C11 | 110.66 (13) | H8A—C8—H8C | 109.5 |
C2—C3—H3A | 111.1 | H8B—C8—H8C | 109.5 |
C2—C3—H3B | 111.1 | C7—C9—H9A | 109.5 |
C2—C3—C4 | 103.20 (13) | C7—C9—H9B | 109.5 |
H3A—C3—H3B | 109.1 | C7—C9—H9C | 109.5 |
H3A—C3—C4 | 111.1 | H9A—C9—H9B | 109.5 |
H3B—C3—C4 | 111.1 | H9A—C9—H9C | 109.5 |
C3—C4—H4 | 111.6 | H9B—C9—H9C | 109.5 |
C3—C4—C5 | 103.00 (13) | C7—C10—H10A | 109.5 |
C3—C4—O5 | 106.72 (13) | C7—C10—H10B | 109.5 |
H4—C4—C5 | 111.6 | C7—C10—H10C | 109.5 |
H4—C4—O5 | 111.6 | H10A—C10—H10B | 109.5 |
C5—C4—O5 | 111.91 (15) | H10A—C10—H10C | 109.5 |
N1—C5—C4 | 102.28 (13) | H10B—C10—H10C | 109.5 |
N1—C5—H5A | 111.3 | C2—C11—O3 | 123.01 (16) |
N1—C5—H5B | 111.3 | C2—C11—O4 | 112.39 (14) |
C4—C5—H5A | 111.3 | O3—C11—O4 | 124.47 (15) |
C4—C5—H5B | 111.3 | C11—O4—C12 | 115.72 (13) |
H5A—C5—H5B | 109.2 | O4—C12—H12A | 109.5 |
N1—C6—O1 | 122.88 (14) | O4—C12—H12B | 109.5 |
N1—C6—O2 | 110.98 (13) | O4—C12—H12C | 109.5 |
O1—C6—O2 | 126.14 (15) | H12A—C12—H12B | 109.5 |
C6—O2—C7 | 121.37 (12) | H12A—C12—H12C | 109.5 |
O2—C7—C8 | 101.97 (13) | H12B—C12—H12C | 109.5 |
O2—C7—C9 | 109.20 (13) | C4—O5—H5 | 109.5 |
C5—N1—C2—C3 | 10.55 (17) | C5—N1—C6—O1 | 174.16 (15) |
C5—N1—C2—C11 | 130.59 (14) | C5—N1—C6—O2 | −5.9 (2) |
C6—N1—C2—C3 | −175.32 (14) | N1—C6—O2—C7 | 175.30 (13) |
C6—N1—C2—C11 | −55.3 (2) | O1—C6—O2—C7 | −4.8 (2) |
N1—C2—C3—C4 | −31.25 (15) | C6—O2—C7—C8 | −172.30 (14) |
C11—C2—C3—C4 | −154.08 (14) | C6—O2—C7—C9 | 70.46 (18) |
C2—C3—C4—C5 | 40.51 (16) | C6—O2—C7—C10 | −54.8 (2) |
C2—C3—C4—O5 | −77.48 (15) | N1—C2—C11—O3 | 151.76 (17) |
C2—N1—C5—C4 | 14.25 (18) | N1—C2—C11—O4 | −32.2 (2) |
C6—N1—C5—C4 | −159.43 (15) | C3—C2—C11—O3 | −92.81 (19) |
C3—C4—C5—N1 | −33.36 (16) | C3—C2—C11—O4 | 83.22 (17) |
O5—C4—C5—N1 | 80.92 (16) | C2—C11—O4—C12 | −177.28 (15) |
C2—N1—C6—O1 | 0.9 (2) | O3—C11—O4—C12 | −1.3 (2) |
C2—N1—C6—O2 | −179.20 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O1i | 0.84 | 1.95 | 2.7831 (16) | 171 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |