Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000839/hb2257sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000839/hb2257Isup2.hkl |
CCDC reference: 638515
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.057
- Data-to-parameter ratio = 9.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C20 H27 N O4
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 27.48 From the CIF: _reflns_number_total 2232 Count of symmetry unique reflns 2235 Completeness (_total/calc) 99.87% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C20H27NO4 | F(000) = 372 |
Mr = 345.43 | Dx = 1.248 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 11172 reflections |
a = 9.7530 (6) Å | θ = 3.0–27.5° |
b = 9.3216 (8) Å | µ = 0.09 mm−1 |
c = 10.792 (7) Å | T = 173 K |
β = 110.462 (4)° | Block, colourless |
V = 919.2 (6) Å3 | 0.50 × 0.50 × 0.45 mm |
Z = 2 |
Nonius KappaCCD diffractometer | 1472 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −12→12 |
380 frames via ω–rotation (ΔΩ= 1°) and two times 10 s per frame (four sets at different κ–angles) scans | k = −12→12 |
11172 measured reflections | l = −14→13 |
2232 independent reflections |
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)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.057 | w = 1/[σ2(Fo2) + (0.0224P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
2232 reflections | Δρmax = 0.16 e Å−3 |
232 parameters | Δρmin = −0.12 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.038 (2) |
Experimental. IR (KBr pellet), cm-1: 3012 (w), 2979 (m), 2952 (m), 2879 (m), 2837 (m), 1690 (s), 1393 (s), 1362 (s), 1083 (s), [α]D22: +127.5 (c 1/5, CHCl3). NMR (most of the signals are duplicated due to the slow conformational inversion), 1H (400 MHz, CDCl3, room temperature): δ 7.53–7.28 (m, 5H), 6.27 (d, 1H), 5.81 (d, 1H), 4.84 (br s, 2H), 4.18 (dd, 1H), 3.83 (m, 1H), 3.71 (m, 1H), 1.69–1.45 (m, 15H); 13C (100.6 MHz, CDCl3, room temperature): δ 152.0 (d), 139.8 (d), 132.5 (s), 128.7 (d), 128.1 (d), 126.4 (d), 123.4 (d), 94.6 (d), 84.4 (d), 80.1 (d), 76.1 (d), 62.7 (d), 59.1 (d), 28.6 (d), 25.8 (d), 24.3 (d), HRMS calculated for C20H27NO4: [M + H]+ = 346.2018; found 346.2043 [M + H]+. |
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 | 0.19109 (15) | 0.37201 (15) | −0.05010 (13) | 0.0402 (4) | |
O2 | −0.10422 (13) | 0.38839 (15) | −0.27736 (12) | 0.0338 (3) | |
O3 | 0.17075 (14) | 0.26211 (16) | −0.48039 (14) | 0.0376 (4) | |
O4 | 0.30194 (13) | 0.45437 (14) | −0.36983 (12) | 0.0300 (3) | |
N1 | 0.09469 (15) | 0.39617 (17) | −0.34033 (14) | 0.0276 (4) | |
C1 | 0.2773 (2) | 0.7649 (2) | −0.04852 (18) | 0.0290 (5) | |
C2 | 0.3607 (2) | 0.7913 (2) | −0.1273 (2) | 0.0359 (5) | |
H2 | 0.3949 | 0.7131 | −0.1650 | 0.043* | |
C3 | 0.3945 (2) | 0.9310 (2) | −0.1517 (2) | 0.0421 (6) | |
H3 | 0.4528 | 0.9476 | −0.2047 | 0.051* | |
C4 | 0.3439 (2) | 1.0453 (3) | −0.0994 (2) | 0.0435 (6) | |
H4 | 0.3660 | 1.1407 | −0.1170 | 0.052* | |
C5 | 0.2610 (2) | 1.0203 (2) | −0.0214 (2) | 0.0439 (6) | |
H5 | 0.2259 | 1.0990 | 0.0150 | 0.053* | |
C6 | 0.2284 (2) | 0.8821 (2) | 0.00421 (18) | 0.0358 (5) | |
H6 | 0.1716 | 0.8666 | 0.0588 | 0.043* | |
C7 | 0.2416 (2) | 0.6176 (2) | −0.0206 (2) | 0.0287 (5) | |
C8 | 0.2146 (2) | 0.5703 (2) | 0.0843 (2) | 0.0363 (5) | |
H8 | 0.2131 | 0.6291 | 0.1557 | 0.044* | |
C9 | 0.1868 (2) | 0.4128 (3) | 0.0756 (2) | 0.0423 (6) | |
H9A | 0.2631 | 0.3617 | 0.1475 | 0.051* | |
H9B | 0.0900 | 0.3911 | 0.0816 | 0.051* | |
C10 | 0.2281 (2) | 0.4934 (2) | −0.11403 (18) | 0.0300 (5) | |
H10 | 0.3248 | 0.4761 | −0.1242 | 0.036* | |
C11 | 0.11126 (19) | 0.5180 (2) | −0.25062 (17) | 0.0265 (5) | |
H11 | 0.1358 | 0.6062 | −0.2914 | 0.032* | |
C12 | −0.0442 (2) | 0.5302 (2) | −0.2491 (2) | 0.0320 (5) | |
H12A | −0.0430 | 0.5628 | −0.1614 | 0.038* | |
H12B | −0.1023 | 0.5990 | −0.3171 | 0.038* | |
C13 | −0.0493 (2) | 0.3239 (2) | −0.37114 (19) | 0.0313 (5) | |
C14 | −0.0338 (2) | 0.1652 (2) | −0.3410 (2) | 0.0406 (6) | |
H14A | 0.0327 | 0.1506 | −0.2499 | 0.061* | |
H14B | 0.0059 | 0.1175 | −0.4021 | 0.061* | |
H14C | −0.1299 | 0.1246 | −0.3516 | 0.061* | |
C15 | −0.1492 (2) | 0.3588 (2) | −0.51085 (19) | 0.0402 (6) | |
H15A | −0.2427 | 0.3087 | −0.5298 | 0.060* | |
H15B | −0.1031 | 0.3276 | −0.5737 | 0.060* | |
H15C | −0.1665 | 0.4625 | −0.5193 | 0.060* | |
C16 | 0.1879 (2) | 0.3624 (2) | −0.40352 (18) | 0.0294 (5) | |
C17 | 0.43261 (19) | 0.4217 (2) | −0.40335 (19) | 0.0292 (5) | |
C18 | 0.5320 (2) | 0.5473 (2) | −0.3428 (2) | 0.0376 (5) | |
H18A | 0.4842 | 0.6368 | −0.3829 | 0.056* | |
H18B | 0.6243 | 0.5366 | −0.3590 | 0.056* | |
H18C | 0.5519 | 0.5497 | −0.2473 | 0.056* | |
C19 | 0.3953 (2) | 0.4190 (2) | −0.55272 (18) | 0.0346 (5) | |
H19A | 0.3294 | 0.3385 | −0.5906 | 0.052* | |
H19B | 0.4854 | 0.4077 | −0.5727 | 0.052* | |
H19C | 0.3472 | 0.5091 | −0.5910 | 0.052* | |
C20 | 0.4995 (2) | 0.2824 (2) | −0.3386 (2) | 0.0383 (6) | |
H20A | 0.5142 | 0.2861 | −0.2441 | 0.057* | |
H20B | 0.5939 | 0.2679 | −0.3500 | 0.057* | |
H20C | 0.4338 | 0.2027 | −0.3799 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0570 (9) | 0.0312 (9) | 0.0288 (8) | −0.0044 (7) | 0.0104 (7) | 0.0004 (7) |
O2 | 0.0313 (7) | 0.0401 (9) | 0.0354 (7) | −0.0051 (7) | 0.0184 (6) | −0.0060 (8) |
O3 | 0.0403 (8) | 0.0389 (9) | 0.0377 (8) | −0.0093 (8) | 0.0190 (7) | −0.0152 (8) |
O4 | 0.0252 (7) | 0.0330 (8) | 0.0356 (8) | −0.0048 (6) | 0.0155 (6) | −0.0065 (6) |
N1 | 0.0244 (8) | 0.0310 (10) | 0.0290 (8) | −0.0072 (8) | 0.0114 (7) | −0.0093 (9) |
C1 | 0.0298 (11) | 0.0310 (12) | 0.0228 (11) | −0.0016 (10) | 0.0051 (9) | −0.0029 (10) |
C2 | 0.0355 (12) | 0.0353 (14) | 0.0376 (13) | −0.0027 (10) | 0.0139 (11) | −0.0051 (11) |
C3 | 0.0409 (12) | 0.0464 (17) | 0.0398 (14) | −0.0077 (11) | 0.0150 (11) | 0.0034 (12) |
C4 | 0.0519 (15) | 0.0322 (14) | 0.0376 (13) | −0.0094 (12) | 0.0044 (12) | 0.0004 (11) |
C5 | 0.0551 (15) | 0.0363 (15) | 0.0372 (13) | 0.0053 (12) | 0.0122 (12) | −0.0024 (11) |
C6 | 0.0441 (12) | 0.0332 (14) | 0.0305 (11) | 0.0018 (11) | 0.0137 (9) | −0.0026 (11) |
C7 | 0.0285 (11) | 0.0308 (12) | 0.0255 (11) | −0.0012 (9) | 0.0078 (9) | −0.0027 (10) |
C8 | 0.0411 (12) | 0.0389 (14) | 0.0277 (12) | −0.0048 (10) | 0.0106 (10) | −0.0072 (11) |
C9 | 0.0493 (13) | 0.0463 (15) | 0.0302 (11) | −0.0080 (12) | 0.0124 (10) | 0.0020 (11) |
C10 | 0.0310 (11) | 0.0293 (12) | 0.0287 (11) | 0.0011 (9) | 0.0090 (9) | 0.0003 (10) |
C11 | 0.0273 (10) | 0.0274 (12) | 0.0257 (11) | −0.0010 (9) | 0.0105 (9) | −0.0022 (9) |
C12 | 0.0311 (11) | 0.0344 (14) | 0.0318 (11) | 0.0005 (10) | 0.0126 (9) | −0.0019 (10) |
C13 | 0.0266 (11) | 0.0386 (13) | 0.0307 (12) | −0.0080 (9) | 0.0125 (9) | −0.0063 (10) |
C14 | 0.0395 (13) | 0.0362 (15) | 0.0497 (14) | −0.0097 (10) | 0.0201 (12) | −0.0033 (12) |
C15 | 0.0327 (11) | 0.0523 (16) | 0.0331 (11) | −0.0090 (11) | 0.0084 (9) | −0.0061 (12) |
C16 | 0.0291 (11) | 0.0335 (14) | 0.0258 (11) | −0.0053 (10) | 0.0099 (9) | −0.0005 (11) |
C17 | 0.0249 (10) | 0.0340 (13) | 0.0320 (11) | 0.0016 (9) | 0.0140 (9) | 0.0028 (10) |
C18 | 0.0280 (11) | 0.0390 (14) | 0.0483 (13) | −0.0029 (10) | 0.0164 (10) | 0.0019 (11) |
C19 | 0.0346 (11) | 0.0386 (14) | 0.0349 (12) | 0.0051 (10) | 0.0175 (9) | 0.0051 (11) |
C20 | 0.0351 (12) | 0.0407 (15) | 0.0389 (13) | 0.0068 (11) | 0.0126 (10) | 0.0046 (11) |
O1—C9 | 1.423 (2) | C9—H9B | 0.9900 |
O1—C10 | 1.435 (2) | C10—C11 | 1.533 (3) |
O2—C13 | 1.432 (2) | C10—H10 | 1.0000 |
O2—C12 | 1.435 (2) | C11—C12 | 1.526 (3) |
O3—C16 | 1.222 (2) | C11—H11 | 1.0000 |
O4—C16 | 1.350 (2) | C12—H12A | 0.9900 |
O4—C17 | 1.473 (2) | C12—H12B | 0.9900 |
N1—C16 | 1.350 (2) | C13—C14 | 1.511 (3) |
N1—C11 | 1.464 (2) | C13—C15 | 1.517 (3) |
N1—C13 | 1.487 (2) | C14—H14A | 0.9800 |
C1—C2 | 1.389 (3) | C14—H14B | 0.9800 |
C1—C6 | 1.390 (3) | C14—H14C | 0.9800 |
C1—C7 | 1.474 (3) | C15—H15A | 0.9800 |
C2—C3 | 1.391 (3) | C15—H15B | 0.9800 |
C2—H2 | 0.9500 | C15—H15C | 0.9800 |
C3—C4 | 1.375 (3) | C17—C20 | 1.510 (3) |
C3—H3 | 0.9500 | C17—C18 | 1.515 (3) |
C4—C5 | 1.376 (3) | C17—C19 | 1.524 (3) |
C4—H4 | 0.9500 | C18—H18A | 0.9800 |
C5—C6 | 1.378 (3) | C18—H18B | 0.9800 |
C5—H5 | 0.9500 | C18—H18C | 0.9800 |
C6—H6 | 0.9500 | C19—H19A | 0.9800 |
C7—C8 | 1.324 (3) | C19—H19B | 0.9800 |
C7—C10 | 1.511 (3) | C19—H19C | 0.9800 |
C8—C9 | 1.490 (3) | C20—H20A | 0.9800 |
C8—H8 | 0.9500 | C20—H20B | 0.9800 |
C9—H9A | 0.9900 | C20—H20C | 0.9800 |
C9—O1—C10 | 110.08 (16) | C11—C12—H12A | 110.7 |
C13—O2—C12 | 108.16 (13) | O2—C12—H12B | 110.7 |
C16—O4—C17 | 120.33 (15) | C11—C12—H12B | 110.7 |
C16—N1—C11 | 125.20 (16) | H12A—C12—H12B | 108.8 |
C16—N1—C13 | 122.10 (15) | O2—C13—N1 | 102.07 (14) |
C11—N1—C13 | 112.13 (13) | O2—C13—C14 | 107.05 (16) |
C2—C1—C6 | 118.0 (2) | N1—C13—C14 | 112.32 (16) |
C2—C1—C7 | 121.37 (19) | O2—C13—C15 | 110.07 (16) |
C6—C1—C7 | 120.61 (17) | N1—C13—C15 | 110.72 (15) |
C1—C2—C3 | 120.6 (2) | C14—C13—C15 | 113.88 (18) |
C1—C2—H2 | 119.7 | C13—C14—H14A | 109.5 |
C3—C2—H2 | 119.7 | C13—C14—H14B | 109.5 |
C4—C3—C2 | 120.34 (19) | H14A—C14—H14B | 109.5 |
C4—C3—H3 | 119.8 | C13—C14—H14C | 109.5 |
C2—C3—H3 | 119.8 | H14A—C14—H14C | 109.5 |
C3—C4—C5 | 119.5 (2) | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 120.3 | C13—C15—H15A | 109.5 |
C5—C4—H4 | 120.3 | C13—C15—H15B | 109.5 |
C4—C5—C6 | 120.4 (2) | H15A—C15—H15B | 109.5 |
C4—C5—H5 | 119.8 | C13—C15—H15C | 109.5 |
C6—C5—H5 | 119.8 | H15A—C15—H15C | 109.5 |
C5—C6—C1 | 121.09 (19) | H15B—C15—H15C | 109.5 |
C5—C6—H6 | 119.5 | O3—C16—O4 | 124.96 (16) |
C1—C6—H6 | 119.5 | O3—C16—N1 | 124.37 (17) |
C8—C7—C1 | 128.09 (18) | O4—C16—N1 | 110.67 (17) |
C8—C7—C10 | 108.58 (18) | O4—C17—C20 | 109.58 (15) |
C1—C7—C10 | 123.33 (17) | O4—C17—C18 | 102.26 (15) |
C7—C8—C9 | 111.12 (19) | C20—C17—C18 | 110.93 (16) |
C7—C8—H8 | 124.4 | O4—C17—C19 | 110.87 (14) |
C9—C8—H8 | 124.4 | C20—C17—C19 | 112.31 (17) |
O1—C9—C8 | 104.96 (18) | C18—C17—C19 | 110.44 (16) |
O1—C9—H9A | 110.8 | C17—C18—H18A | 109.5 |
C8—C9—H9A | 110.8 | C17—C18—H18B | 109.5 |
O1—C9—H9B | 110.8 | H18A—C18—H18B | 109.5 |
C8—C9—H9B | 110.8 | C17—C18—H18C | 109.5 |
H9A—C9—H9B | 108.8 | H18A—C18—H18C | 109.5 |
O1—C10—C7 | 105.15 (15) | H18B—C18—H18C | 109.5 |
O1—C10—C11 | 110.67 (15) | C17—C19—H19A | 109.5 |
C7—C10—C11 | 112.94 (16) | C17—C19—H19B | 109.5 |
O1—C10—H10 | 109.3 | H19A—C19—H19B | 109.5 |
C7—C10—H10 | 109.3 | C17—C19—H19C | 109.5 |
C11—C10—H10 | 109.3 | H19A—C19—H19C | 109.5 |
N1—C11—C12 | 100.65 (14) | H19B—C19—H19C | 109.5 |
N1—C11—C10 | 113.15 (16) | C17—C20—H20A | 109.5 |
C12—C11—C10 | 114.06 (15) | C17—C20—H20B | 109.5 |
N1—C11—H11 | 109.5 | H20A—C20—H20B | 109.5 |
C12—C11—H11 | 109.5 | C17—C20—H20C | 109.5 |
C10—C11—H11 | 109.5 | H20A—C20—H20C | 109.5 |
O2—C12—C11 | 105.17 (15) | H20B—C20—H20C | 109.5 |
O2—C12—H12A | 110.7 | ||
C6—C1—C2—C3 | 0.3 (3) | O1—C10—C11—N1 | −60.73 (19) |
C7—C1—C2—C3 | −179.37 (19) | C7—C10—C11—N1 | −178.30 (14) |
C1—C2—C3—C4 | −0.9 (3) | O1—C10—C11—C12 | 53.5 (2) |
C2—C3—C4—C5 | 0.8 (3) | C7—C10—C11—C12 | −64.0 (2) |
C3—C4—C5—C6 | −0.1 (3) | C13—O2—C12—C11 | −36.31 (19) |
C4—C5—C6—C1 | −0.5 (3) | N1—C11—C12—O2 | 26.85 (18) |
C2—C1—C6—C5 | 0.4 (3) | C10—C11—C12—O2 | −94.63 (18) |
C7—C1—C6—C5 | −179.9 (2) | C12—O2—C13—N1 | 28.89 (18) |
C2—C1—C7—C8 | 152.4 (2) | C12—O2—C13—C14 | 147.05 (16) |
C6—C1—C7—C8 | −27.4 (3) | C12—O2—C13—C15 | −88.70 (18) |
C2—C1—C7—C10 | −28.6 (3) | C16—N1—C13—O2 | 177.31 (16) |
C6—C1—C7—C10 | 151.67 (19) | C11—N1—C13—O2 | −10.93 (19) |
C1—C7—C8—C9 | −178.60 (19) | C16—N1—C13—C14 | 63.0 (2) |
C10—C7—C8—C9 | 2.3 (2) | C11—N1—C13—C14 | −125.26 (18) |
C10—O1—C9—C8 | 3.3 (2) | C16—N1—C13—C15 | −65.6 (2) |
C7—C8—C9—O1 | −3.5 (2) | C11—N1—C13—C15 | 106.20 (17) |
C9—O1—C10—C7 | −2.09 (19) | C17—O4—C16—O3 | −12.9 (3) |
C9—O1—C10—C11 | −124.34 (16) | C17—O4—C16—N1 | 166.95 (15) |
C8—C7—C10—O1 | −0.2 (2) | C11—N1—C16—O3 | −178.32 (18) |
C1—C7—C10—O1 | −179.34 (17) | C13—N1—C16—O3 | −7.7 (3) |
C8—C7—C10—C11 | 120.61 (18) | C11—N1—C16—O4 | 1.8 (2) |
C1—C7—C10—C11 | −58.6 (2) | C13—N1—C16—O4 | 172.44 (16) |
C16—N1—C11—C12 | 161.82 (17) | C16—O4—C17—C20 | −59.8 (2) |
C13—N1—C11—C12 | −9.64 (19) | C16—O4—C17—C18 | −177.57 (15) |
C16—N1—C11—C10 | −76.1 (2) | C16—O4—C17—C19 | 64.7 (2) |
C13—N1—C11—C10 | 112.48 (17) |