Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008489/fr1265sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008489/fr1265Isup2.hkl |
CCDC reference: 150855
Data collection: SMART (Bruker, 1997a); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C14H21NO5 | Z = 2 |
Mr = 283.32 | F(000) = 304 |
Triclinic, P1 | Dx = 1.279 Mg m−3 |
a = 8.5710 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5382 (9) Å | Cell parameters from 74 reflections |
c = 10.3449 (9) Å | θ = 2.1–27.0° |
α = 105.7991 (10)° | µ = 0.10 mm−1 |
β = 94.1123 (11)° | T = 193 K |
γ = 112.6952 (13)° | Block, colorless |
V = 735.72 (12) Å3 | 0.40 × 0.20 × 0.20 mm |
CCD area detector diffractometer | 2392 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 25.4°, θmin = 2.1° |
phi and ω scans | h = −10→9 |
3851 measured reflections | k = −10→12 |
2688 independent reflections | l = −12→10 |
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.4327P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.005 |
2688 reflections | Δρmax = 0.30 e Å−3 |
182 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Bruker, 1997b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (4) |
Experimental. Data were acquired on a three-circle Bruker CCD diffractometer and detector with mounted LT-2 low temperature apparatus operating at 213 K. The crystal was mounted on the glass fiber of the goniometer head using silicone grease for adhesion. The cell constants were determined from 60 thirty-second frames. Data were measured using omega scans of 0.3° and 30 - s per frame until completion of the collection hemisphere. A complete hemisphere consisting of 1272 frames was collected in all with a maximum 0.83 Angstrom resolution. A fourth data collection iteration of 50 frames was collected in order to monitor for crystal decay (<1%). Cell parameters were retrieved using SMART (Bruker, 1997) software and refined using SAINT (Bruker, 1997) on all observed reflections. Data reduction was achieved through the use of the SAINT software, which corrects for Lp and decay. Absorption corrections were applied using SADABS supplied by George Sheldrick based on method of Blessing(1995). The structures are solved by the direct method using the SHELXS97 program (Sheldrick, 1990) and refined by least squares method on F2 SHELXL97 (Sheldrick, 1997), incorporated in SHELXTL-PC V 5.10 (Bruker, 1997). Non hydrogen atoms were refined anisotropically, whereas hydrogen atoms were located from difference map and subsequently refined isotropically. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.68566 (16) | 0.50891 (15) | 0.94588 (13) | 0.0346 (3) | |
O2 | 0.4294 (2) | −0.01121 (17) | 0.73592 (14) | 0.0453 (4) | |
O3 | 0.31381 (18) | 0.05417 (15) | 0.91888 (13) | 0.0371 (3) | |
O4 | 0.21280 (15) | 0.15184 (14) | 0.61285 (12) | 0.0292 (3) | |
O5 | 0.34379 (15) | 0.40112 (14) | 0.57755 (12) | 0.0286 (3) | |
N1 | 0.6131 (2) | 0.35593 (19) | 0.96175 (15) | 0.0340 (4) | |
C1 | 0.6080 (2) | 0.5001 (2) | 0.82283 (17) | 0.0289 (4) | |
C2 | 0.4866 (2) | 0.3484 (2) | 0.75691 (17) | 0.0255 (4) | |
C3 | 0.4981 (2) | 0.2639 (2) | 0.84897 (17) | 0.0281 (4) | |
C4 | 0.4097 (2) | 0.0868 (2) | 0.82610 (17) | 0.0296 (4) | |
C5 | 0.2298 (3) | −0.1158 (2) | 0.9064 (2) | 0.0427 (5) | |
H5A | 0.3157 | −0.1617 | 0.9042 | 0.051* | |
H5B | 0.1413 | −0.1766 | 0.8208 | 0.051* | |
C6 | 0.1474 (3) | −0.1264 (3) | 1.0288 (2) | 0.0471 (5) | |
H6A | 0.0898 | −0.2392 | 1.0238 | 0.071* | |
H6B | 0.0623 | −0.0810 | 1.0297 | 0.071* | |
H6C | 0.2362 | −0.0658 | 1.1128 | 0.071* | |
C7 | 0.6729 (3) | 0.6518 (2) | 0.7889 (2) | 0.0383 (5) | |
H7A | 0.6093 | 0.6334 | 0.6989 | 0.057* | |
H7B | 0.7960 | 0.6870 | 0.7872 | 0.057* | |
H7C | 0.6560 | 0.7350 | 0.8585 | 0.057* | |
C8 | 0.3712 (2) | 0.2792 (2) | 0.61569 (17) | 0.0259 (4) | |
C9 | 0.1001 (2) | 0.2027 (2) | 0.68997 (19) | 0.0313 (4) | |
H9A | 0.1541 | 0.2488 | 0.7886 | 0.038* | |
H9B | −0.0099 | 0.1084 | 0.6777 | 0.038* | |
C10 | 0.0629 (2) | 0.3280 (2) | 0.64413 (19) | 0.0308 (4) | |
C11 | 0.2389 (2) | 0.4620 (2) | 0.65640 (18) | 0.0290 (4) | |
H11A | 0.2233 | 0.5450 | 0.6237 | 0.035* | |
H11B | 0.2981 | 0.5131 | 0.7539 | 0.035* | |
C12 | 0.4534 (3) | 0.2072 (2) | 0.50732 (19) | 0.0378 (5) | |
H12A | 0.3765 | 0.1636 | 0.4175 | 0.057* | |
H12B | 0.4732 | 0.1209 | 0.5290 | 0.057* | |
H12C | 0.5638 | 0.2907 | 0.5053 | 0.057* | |
C13 | −0.0370 (3) | 0.2545 (2) | 0.4957 (2) | 0.0411 (5) | |
H13A | −0.0598 | 0.3362 | 0.4678 | 0.062* | |
H13B | −0.1467 | 0.1644 | 0.4887 | 0.062* | |
H13C | 0.0315 | 0.2159 | 0.4357 | 0.062* | |
C14 | −0.0375 (3) | 0.3947 (3) | 0.7400 (2) | 0.0438 (5) | |
H14A | 0.0288 | 0.4411 | 0.8342 | 0.066* | |
H14B | −0.1488 | 0.3077 | 0.7350 | 0.066* | |
H14C | −0.0569 | 0.4780 | 0.7124 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0337 (7) | 0.0352 (7) | 0.0308 (7) | 0.0134 (6) | −0.0007 (5) | 0.0079 (5) |
O2 | 0.0656 (10) | 0.0397 (8) | 0.0409 (8) | 0.0308 (7) | 0.0196 (7) | 0.0134 (6) |
O3 | 0.0488 (8) | 0.0312 (7) | 0.0368 (7) | 0.0187 (6) | 0.0152 (6) | 0.0150 (6) |
O4 | 0.0291 (6) | 0.0258 (6) | 0.0337 (7) | 0.0128 (5) | 0.0038 (5) | 0.0098 (5) |
O5 | 0.0337 (7) | 0.0325 (7) | 0.0279 (6) | 0.0180 (5) | 0.0087 (5) | 0.0157 (5) |
N1 | 0.0392 (9) | 0.0358 (9) | 0.0301 (8) | 0.0188 (7) | 0.0032 (7) | 0.0118 (7) |
C1 | 0.0272 (9) | 0.0349 (9) | 0.0267 (9) | 0.0157 (7) | 0.0055 (7) | 0.0090 (7) |
C2 | 0.0259 (8) | 0.0314 (9) | 0.0260 (8) | 0.0170 (7) | 0.0092 (7) | 0.0113 (7) |
C3 | 0.0310 (9) | 0.0339 (9) | 0.0255 (8) | 0.0194 (8) | 0.0076 (7) | 0.0102 (7) |
C4 | 0.0352 (9) | 0.0351 (10) | 0.0259 (9) | 0.0215 (8) | 0.0037 (7) | 0.0118 (7) |
C5 | 0.0543 (12) | 0.0320 (10) | 0.0445 (11) | 0.0169 (9) | 0.0101 (10) | 0.0183 (9) |
C6 | 0.0498 (13) | 0.0466 (12) | 0.0552 (13) | 0.0211 (10) | 0.0156 (10) | 0.0298 (10) |
C7 | 0.0363 (10) | 0.0332 (10) | 0.0402 (11) | 0.0089 (8) | 0.0050 (8) | 0.0132 (8) |
C8 | 0.0296 (9) | 0.0269 (8) | 0.0262 (8) | 0.0151 (7) | 0.0064 (7) | 0.0114 (7) |
C9 | 0.0272 (9) | 0.0338 (10) | 0.0377 (10) | 0.0140 (7) | 0.0088 (7) | 0.0169 (8) |
C10 | 0.0283 (9) | 0.0326 (9) | 0.0365 (10) | 0.0162 (8) | 0.0054 (7) | 0.0142 (8) |
C11 | 0.0312 (9) | 0.0289 (9) | 0.0321 (9) | 0.0164 (7) | 0.0060 (7) | 0.0126 (7) |
C12 | 0.0478 (11) | 0.0470 (12) | 0.0276 (9) | 0.0295 (10) | 0.0118 (8) | 0.0109 (8) |
C13 | 0.0379 (10) | 0.0385 (11) | 0.0450 (11) | 0.0175 (9) | −0.0062 (9) | 0.0127 (9) |
C14 | 0.0390 (11) | 0.0503 (12) | 0.0551 (13) | 0.0274 (10) | 0.0169 (10) | 0.0220 (10) |
O1—C1 | 1.359 (2) | C7—H7A | 0.9800 |
O1—N1 | 1.410 (2) | C7—H7B | 0.9800 |
O2—C4 | 1.201 (2) | C7—H7C | 0.9800 |
O3—C4 | 1.331 (2) | C8—C12 | 1.514 (2) |
O3—C5 | 1.462 (2) | C9—C10 | 1.528 (2) |
O4—C8 | 1.422 (2) | C9—H9A | 0.9900 |
O4—C9 | 1.438 (2) | C9—H9B | 0.9900 |
O5—C8 | 1.418 (2) | C10—C11 | 1.523 (2) |
O5—C11 | 1.436 (2) | C10—C14 | 1.526 (3) |
N1—C3 | 1.309 (2) | C10—C13 | 1.531 (3) |
C1—C2 | 1.357 (2) | C11—H11A | 0.9900 |
C1—C7 | 1.486 (3) | C11—H11B | 0.9900 |
C2—C3 | 1.425 (2) | C12—H12A | 0.9800 |
C2—C8 | 1.520 (2) | C12—H12B | 0.9800 |
C3—C4 | 1.501 (2) | C12—H12C | 0.9800 |
C5—C6 | 1.502 (3) | C13—H13A | 0.9800 |
C5—H5A | 0.9900 | C13—H13B | 0.9800 |
C5—H5B | 0.9900 | C13—H13C | 0.9800 |
C6—H6A | 0.9800 | C14—H14A | 0.9800 |
C6—H6B | 0.9800 | C14—H14B | 0.9800 |
C6—H6C | 0.9800 | C14—H14C | 0.9800 |
C1—O1—N1 | 108.82 (13) | O4—C8—C2 | 110.15 (13) |
C4—O3—C5 | 115.16 (14) | C12—C8—C2 | 111.17 (14) |
C8—O4—C9 | 114.37 (12) | O4—C9—C10 | 111.44 (14) |
C8—O5—C11 | 113.54 (12) | O4—C9—H9A | 109.3 |
C3—N1—O1 | 104.81 (14) | C10—C9—H9A | 109.3 |
C2—C1—O1 | 110.05 (15) | O4—C9—H9B | 109.3 |
C2—C1—C7 | 134.39 (16) | C10—C9—H9B | 109.3 |
O1—C1—C7 | 115.55 (15) | H9A—C9—H9B | 108.0 |
C1—C2—C3 | 103.36 (15) | C11—C10—C14 | 109.40 (15) |
C1—C2—C8 | 129.33 (15) | C11—C10—C9 | 105.59 (14) |
C3—C2—C8 | 127.23 (15) | C14—C10—C9 | 109.82 (16) |
N1—C3—C2 | 112.96 (16) | C11—C10—C13 | 110.58 (16) |
N1—C3—C4 | 118.36 (15) | C14—C10—C13 | 110.89 (16) |
C2—C3—C4 | 128.40 (15) | C9—C10—C13 | 110.41 (15) |
O2—C4—O3 | 125.16 (17) | O5—C11—C10 | 111.16 (14) |
O2—C4—C3 | 122.60 (17) | O5—C11—H11A | 109.4 |
O3—C4—C3 | 112.21 (14) | C10—C11—H11A | 109.4 |
O3—C5—C6 | 107.30 (16) | O5—C11—H11B | 109.4 |
O3—C5—H5A | 110.3 | C10—C11—H11B | 109.4 |
C6—C5—H5A | 110.3 | H11A—C11—H11B | 108.0 |
O3—C5—H5B | 110.3 | C8—C12—H12A | 109.5 |
C6—C5—H5B | 110.3 | C8—C12—H12B | 109.5 |
H5A—C5—H5B | 108.5 | H12A—C12—H12B | 109.5 |
C5—C6—H6A | 109.5 | C8—C12—H12C | 109.5 |
C5—C6—H6B | 109.5 | H12A—C12—H12C | 109.5 |
H6A—C6—H6B | 109.5 | H12B—C12—H12C | 109.5 |
C5—C6—H6C | 109.5 | C10—C13—H13A | 109.5 |
H6A—C6—H6C | 109.5 | C10—C13—H13B | 109.5 |
H6B—C6—H6C | 109.5 | H13A—C13—H13B | 109.5 |
C1—C7—H7A | 109.5 | C10—C13—H13C | 109.5 |
C1—C7—H7B | 109.5 | H13A—C13—H13C | 109.5 |
H7A—C7—H7B | 109.5 | H13B—C13—H13C | 109.5 |
C1—C7—H7C | 109.5 | C10—C14—H14A | 109.5 |
H7A—C7—H7C | 109.5 | C10—C14—H14B | 109.5 |
H7B—C7—H7C | 109.5 | H14A—C14—H14B | 109.5 |
O5—C8—O4 | 111.63 (13) | C10—C14—H14C | 109.5 |
O5—C8—C12 | 106.73 (14) | H14A—C14—H14C | 109.5 |
O4—C8—C12 | 106.27 (14) | H14B—C14—H14C | 109.5 |
O5—C8—C2 | 110.76 (13) | ||
C1—O1—N1—C3 | 0.43 (18) | C11—O5—C8—C12 | 169.54 (14) |
N1—O1—C1—C2 | 0.34 (18) | C11—O5—C8—C2 | −69.31 (17) |
N1—O1—C1—C7 | −178.79 (15) | C9—O4—C8—O5 | −52.55 (18) |
O1—C1—C2—C3 | −0.89 (18) | C9—O4—C8—C12 | −168.54 (14) |
C7—C1—C2—C3 | 178.00 (19) | C9—O4—C8—C2 | 70.94 (17) |
O1—C1—C2—C8 | −177.80 (15) | C1—C2—C8—O5 | −26.4 (2) |
C7—C1—C2—C8 | 1.1 (3) | C3—C2—C8—O5 | 157.39 (15) |
O1—N1—C3—C2 | −1.03 (19) | C1—C2—C8—O4 | −150.38 (16) |
O1—N1—C3—C4 | 173.42 (14) | C3—C2—C8—O4 | 33.4 (2) |
C1—C2—C3—N1 | 1.23 (19) | C1—C2—C8—C12 | 92.1 (2) |
C8—C2—C3—N1 | 178.22 (16) | C3—C2—C8—C12 | −84.1 (2) |
C1—C2—C3—C4 | −172.54 (16) | C8—O4—C9—C10 | 55.23 (19) |
C8—C2—C3—C4 | 4.5 (3) | O4—C9—C10—C11 | −54.89 (18) |
C5—O3—C4—O2 | 0.5 (3) | O4—C9—C10—C14 | −172.74 (15) |
C5—O3—C4—C3 | −177.43 (15) | O4—C9—C10—C13 | 64.67 (19) |
N1—C3—C4—O2 | −113.8 (2) | C8—O5—C11—C10 | −58.18 (18) |
C2—C3—C4—O2 | 59.7 (3) | C14—C10—C11—O5 | 174.55 (14) |
N1—C3—C4—O3 | 64.2 (2) | C9—C10—C11—O5 | 56.42 (18) |
C2—C3—C4—O3 | −122.30 (18) | C13—C10—C11—O5 | −63.03 (18) |
C4—O3—C5—C6 | 172.98 (16) | C2—C8—O4—C9 | 70.9 (2) |
C11—O5—C8—O4 | 53.83 (17) | C2—C8—O5—C11 | −69.3 (2) |
Compound | C2-C3-C4-O3_angles(°) |
(I) | 62.8 (1) |
(II) | 175.8 (2) |
(III) | -1.6 (3) |
(IV) | 108.2 (3) |
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