Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022129/ac6180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022129/ac6180Isup2.hkl |
CCDC reference: 282224
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.006 Å
- R factor = 0.049
- wR factor = 0.126
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.20 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.54 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 26.01 From the CIF: _reflns_number_total 1928 Count of symmetry unique reflns 1928 Completeness (_total/calc) 100.00% 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 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).
C20H23NO4 | Dx = 1.334 Mg m−3 |
Mr = 341.39 | Melting point = 405–406 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 22 reflections |
a = 8.628 (2) Å | θ = 18.3–19.7° |
b = 12.727 (2) Å | µ = 0.09 mm−1 |
c = 15.4842 (19) Å | T = 290 K |
V = 1700.3 (5) Å3 | Prism, colorles |
Z = 4 | 0.25 × 0.25 × 0.25 mm |
F(000) = 728 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.077 |
Radiation source: fine-focus sealed tube | θmax = 26.0°, θmin = 2.1° |
Graphite monochromator | h = 0→10 |
non–profiled ω/2θ scans | k = 0→15 |
4181 measured reflections | l = −19→19 |
1928 independent reflections | 3 standard reflections every 120 min |
1093 reflections with I > 2σ(I) | intensity decay: 5% |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0562P)2] where P = (Fo2 + 2Fc2)/3 |
1928 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Experimental. Spectroscopic analysis: IR (KBr pellet, cm-1). The νC—H vibrations of the aromatic ring (A) appears at 3065w and 3024m. The bend at 3000 was assigned to the νC—H of double C—C bond. The middle intensity bands between 2961 and 2811 are attributed to νC—H vibrations of methine, methilene. The very strong band at 1735 was ascribed to νC=O of the acetyl group. The middle band at 1617 is attributed to νC=C bond. The band at 1609 belongs to 8a radial vibration of aromatic ring A. The bands at 1504 an 1449 could be attributed to 19a and 19b vibrations of the aromatic ring. The series of very strong bands between 1202 and 1234 can be assigned to different νC—O vibrations. The bands between 821 and 741 could be attributed to out-of-plane C—H vibrations of aromatic ring. |
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 | ||
C1 | 0.6225 (6) | 0.3247 (4) | 0.1383 (3) | 0.0483 (12) | |
H1 | 0.5502 | 0.3233 | 0.0938 | 0.058* | |
C2 | 0.7799 (5) | 0.3328 (4) | 0.1186 (3) | 0.0473 (12) | |
H2 | 0.8102 | 0.3344 | 0.0610 | 0.057* | |
C3 | 0.8914 (5) | 0.3385 (4) | 0.1818 (3) | 0.0439 (11) | |
C4 | 0.8413 (5) | 0.3333 (3) | 0.2660 (2) | 0.0370 (10) | |
C5 | 0.8181 (5) | 0.3677 (4) | 0.4090 (3) | 0.0400 (11) | |
H5 | 0.8542 | 0.3394 | 0.4643 | 0.048* | |
C6 | 0.8011 (5) | 0.4887 (4) | 0.4152 (3) | 0.0466 (12) | |
H6 | 0.8361 | 0.5108 | 0.4726 | 0.056* | |
C7 | 0.6423 (5) | 0.5318 (4) | 0.4006 (3) | 0.0484 (12) | |
H7 | 0.6329 | 0.6041 | 0.3933 | 0.058* | |
C8 | 0.5146 (5) | 0.4752 (4) | 0.3975 (3) | 0.0476 (12) | |
H8 | 0.4208 | 0.5098 | 0.3890 | 0.057* | |
C9 | 0.3877 (5) | 0.3035 (4) | 0.3535 (3) | 0.0447 (12) | |
H9 | 0.2883 | 0.3352 | 0.3696 | 0.054* | |
C10 | 0.4069 (5) | 0.3193 (4) | 0.2553 (3) | 0.0456 (12) | |
H10A | 0.3505 | 0.2640 | 0.2257 | 0.055* | |
H10B | 0.3596 | 0.3857 | 0.2394 | 0.055* | |
C11 | 0.5721 (5) | 0.3189 (3) | 0.2236 (2) | 0.0396 (11) | |
C12 | 0.6867 (5) | 0.3202 (3) | 0.2853 (2) | 0.0353 (10) | |
C13 | 0.6682 (5) | 0.3110 (4) | 0.3811 (2) | 0.0377 (11) | |
C14 | 0.5126 (5) | 0.3586 (4) | 0.4068 (3) | 0.0446 (12) | |
H14 | 0.4942 | 0.3421 | 0.4677 | 0.054* | |
C15 | 0.6655 (5) | 0.1945 (3) | 0.4083 (3) | 0.0459 (12) | |
H15A | 0.7613 | 0.1610 | 0.3906 | 0.055* | |
H15B | 0.6583 | 0.1899 | 0.4707 | 0.055* | |
C16 | 0.5293 (6) | 0.1374 (4) | 0.3679 (3) | 0.0517 (13) | |
H16A | 0.5464 | 0.1306 | 0.3062 | 0.062* | |
H16B | 0.5219 | 0.0673 | 0.3921 | 0.062* | |
C17 | 0.2511 (6) | 0.1353 (5) | 0.3509 (3) | 0.0714 (17) | |
H17A | 0.1580 | 0.1742 | 0.3622 | 0.107* | |
H17B | 0.2458 | 0.0685 | 0.3796 | 0.107* | |
H17C | 0.2619 | 0.1245 | 0.2899 | 0.107* | |
C18 | 1.1006 (6) | 0.3568 (7) | 0.0835 (3) | 0.113 (3) | |
H19A | 1.2114 | 0.3635 | 0.0829 | 0.170* | |
H19B | 1.0549 | 0.4177 | 0.0572 | 0.170* | |
H19C | 1.0709 | 0.2952 | 0.0517 | 0.170* | |
C19 | 1.0504 (6) | 0.5448 (4) | 0.3678 (4) | 0.0550 (13) | |
C20 | 1.1353 (6) | 0.5749 (4) | 0.2888 (3) | 0.0673 (16) | |
H20A | 1.0627 | 0.5894 | 0.2434 | 0.101* | |
H20B | 1.2022 | 0.5184 | 0.2716 | 0.101* | |
H20C | 1.1962 | 0.6365 | 0.3001 | 0.101* | |
N1 | 0.3838 (4) | 0.1937 (3) | 0.3830 (2) | 0.0490 (10) | |
O1 | 1.0489 (4) | 0.3480 (3) | 0.16893 (19) | 0.0593 (10) | |
O2 | 0.9292 (3) | 0.3416 (2) | 0.34055 (16) | 0.0445 (8) | |
O3 | 0.8967 (4) | 0.5397 (3) | 0.3518 (2) | 0.0510 (8) | |
O4 | 1.1055 (4) | 0.5238 (4) | 0.4367 (3) | 0.0827 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (3) | 0.064 (3) | 0.031 (2) | 0.005 (3) | −0.007 (2) | 0.005 (2) |
C2 | 0.052 (3) | 0.065 (3) | 0.025 (2) | 0.006 (3) | 0.004 (2) | −0.001 (2) |
C3 | 0.041 (3) | 0.053 (3) | 0.038 (2) | 0.005 (3) | 0.003 (2) | −0.002 (2) |
C4 | 0.039 (3) | 0.045 (3) | 0.0275 (19) | 0.009 (2) | −0.004 (2) | 0.002 (2) |
C5 | 0.036 (3) | 0.063 (3) | 0.0212 (19) | 0.005 (2) | 0.0028 (19) | −0.001 (2) |
C6 | 0.047 (3) | 0.061 (3) | 0.032 (2) | 0.001 (3) | −0.001 (2) | −0.002 (2) |
C7 | 0.045 (3) | 0.051 (3) | 0.049 (3) | 0.008 (3) | 0.006 (2) | −0.004 (2) |
C8 | 0.037 (3) | 0.066 (3) | 0.039 (2) | 0.007 (3) | 0.002 (2) | −0.010 (2) |
C9 | 0.032 (2) | 0.065 (3) | 0.037 (2) | 0.001 (2) | 0.005 (2) | −0.002 (2) |
C10 | 0.040 (3) | 0.058 (3) | 0.039 (2) | −0.001 (3) | −0.004 (2) | 0.002 (2) |
C11 | 0.043 (3) | 0.047 (3) | 0.029 (2) | 0.004 (2) | −0.004 (2) | −0.002 (2) |
C12 | 0.039 (3) | 0.038 (2) | 0.029 (2) | 0.004 (2) | 0.0005 (19) | −0.0011 (18) |
C13 | 0.035 (2) | 0.052 (3) | 0.0257 (19) | 0.003 (2) | −0.0005 (19) | 0.0003 (19) |
C14 | 0.041 (3) | 0.059 (3) | 0.034 (2) | 0.002 (2) | 0.005 (2) | −0.004 (2) |
C15 | 0.045 (3) | 0.057 (3) | 0.036 (2) | 0.003 (3) | −0.001 (2) | 0.006 (2) |
C16 | 0.063 (3) | 0.049 (3) | 0.043 (2) | −0.005 (3) | 0.001 (3) | 0.003 (2) |
C17 | 0.055 (4) | 0.090 (4) | 0.070 (4) | −0.024 (3) | −0.004 (3) | 0.001 (3) |
C18 | 0.053 (4) | 0.239 (9) | 0.048 (3) | 0.001 (5) | 0.017 (3) | 0.027 (5) |
C19 | 0.049 (3) | 0.051 (3) | 0.065 (3) | 0.001 (3) | 0.002 (3) | 0.005 (3) |
C20 | 0.055 (3) | 0.063 (3) | 0.084 (4) | 0.002 (3) | 0.018 (3) | 0.015 (3) |
N1 | 0.043 (2) | 0.064 (3) | 0.041 (2) | −0.007 (2) | 0.0013 (18) | −0.0004 (19) |
O1 | 0.0383 (18) | 0.101 (3) | 0.0390 (17) | 0.004 (2) | 0.0098 (15) | 0.0068 (19) |
O2 | 0.0371 (18) | 0.061 (2) | 0.0358 (16) | 0.0061 (16) | 0.0032 (13) | −0.0018 (15) |
O3 | 0.0388 (19) | 0.061 (2) | 0.0531 (19) | −0.0020 (17) | 0.0007 (16) | 0.0095 (16) |
O4 | 0.052 (2) | 0.125 (4) | 0.071 (3) | −0.013 (2) | −0.013 (2) | 0.016 (2) |
C1—C11 | 1.392 (6) | C10—H10B | 0.9700 |
C1—C2 | 1.396 (6) | C11—C12 | 1.374 (5) |
C1—H1 | 0.9300 | C12—C13 | 1.497 (5) |
C2—C3 | 1.374 (6) | C13—C14 | 1.526 (6) |
C2—H2 | 0.9300 | C13—C15 | 1.541 (6) |
C3—C4 | 1.376 (6) | C14—H14 | 0.9800 |
C3—O1 | 1.379 (5) | C15—C16 | 1.517 (6) |
C4—C12 | 1.377 (6) | C15—H15A | 0.9700 |
C4—O2 | 1.385 (4) | C15—H15B | 0.9700 |
C5—O2 | 1.467 (5) | C16—N1 | 1.464 (6) |
C5—C13 | 1.542 (6) | C16—H16A | 0.9700 |
C5—C6 | 1.550 (6) | C16—H16B | 0.9700 |
C5—H5 | 0.9800 | C17—N1 | 1.453 (6) |
C6—O3 | 1.437 (5) | C17—H17A | 0.9600 |
C6—C7 | 1.493 (6) | C17—H17B | 0.9600 |
C6—H6 | 0.9800 | C17—H17C | 0.9600 |
C7—C8 | 1.318 (7) | C18—O1 | 1.401 (5) |
C7—H7 | 0.9300 | C18—H19A | 0.9600 |
C8—C14 | 1.491 (7) | C18—H19B | 0.9600 |
C8—H8 | 0.9300 | C18—H19C | 0.9600 |
C9—N1 | 1.471 (6) | C19—O4 | 1.198 (6) |
C9—C14 | 1.527 (6) | C19—O3 | 1.350 (6) |
C9—C10 | 1.543 (6) | C19—C20 | 1.476 (7) |
C9—H9 | 0.9800 | C20—H20A | 0.9600 |
C10—C11 | 1.508 (5) | C20—H20B | 0.9600 |
C10—H10A | 0.9700 | C20—H20C | 0.9600 |
C11—C1—C2 | 121.0 (4) | C14—C13—C15 | 107.3 (4) |
C11—C1—H1 | 119.5 | C12—C13—C5 | 98.7 (3) |
C2—C1—H1 | 119.5 | C14—C13—C5 | 118.6 (3) |
C3—C2—C1 | 121.9 (4) | C15—C13—C5 | 112.7 (4) |
C3—C2—H2 | 119.0 | C8—C14—C13 | 111.1 (4) |
C1—C2—H2 | 119.0 | C8—C14—C9 | 114.4 (4) |
C2—C3—C4 | 116.9 (4) | C13—C14—C9 | 107.3 (3) |
C2—C3—O1 | 126.3 (4) | C8—C14—H14 | 107.9 |
C4—C3—O1 | 116.8 (4) | C13—C14—H14 | 107.9 |
C3—C4—C12 | 121.0 (4) | C9—C14—H14 | 107.9 |
C3—C4—O2 | 127.9 (4) | C16—C15—C13 | 111.1 (4) |
C12—C4—O2 | 111.1 (3) | C16—C15—H15A | 109.4 |
O2—C5—C13 | 103.9 (3) | C13—C15—H15A | 109.4 |
O2—C5—C6 | 109.3 (3) | C16—C15—H15B | 109.4 |
C13—C5—C6 | 113.8 (4) | C13—C15—H15B | 109.4 |
O2—C5—H5 | 109.9 | H15A—C15—H15B | 108.0 |
C13—C5—H5 | 109.9 | N1—C16—C15 | 111.3 (4) |
C6—C5—H5 | 109.9 | N1—C16—H16A | 109.4 |
O3—C6—C7 | 104.9 (4) | C15—C16—H16A | 109.4 |
O3—C6—C5 | 110.7 (4) | N1—C16—H16B | 109.4 |
C7—C6—C5 | 116.3 (4) | C15—C16—H16B | 109.4 |
O3—C6—H6 | 108.2 | H16A—C16—H16B | 108.0 |
C7—C6—H6 | 108.2 | N1—C17—H17A | 109.5 |
C5—C6—H6 | 108.2 | N1—C17—H17B | 109.5 |
C8—C7—C6 | 124.9 (5) | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 117.6 | N1—C17—H17C | 109.5 |
C6—C7—H7 | 117.6 | H17A—C17—H17C | 109.5 |
C7—C8—C14 | 123.4 (5) | H17B—C17—H17C | 109.5 |
C7—C8—H8 | 118.3 | O1—C18—H19A | 109.5 |
C14—C8—H8 | 118.3 | O1—C18—H19B | 109.5 |
N1—C9—C14 | 106.5 (4) | H19A—C18—H19B | 109.5 |
N1—C9—C10 | 115.6 (4) | O1—C18—H19C | 109.5 |
C14—C9—C10 | 113.4 (4) | H19A—C18—H19C | 109.5 |
N1—C9—H9 | 106.9 | H19B—C18—H19C | 109.5 |
C14—C9—H9 | 106.9 | O4—C19—O3 | 122.9 (5) |
C10—C9—H9 | 106.9 | O4—C19—C20 | 126.8 (5) |
C11—C10—C9 | 114.9 (3) | O3—C19—C20 | 110.3 (5) |
C11—C10—H10A | 108.5 | C19—C20—H20A | 109.5 |
C9—C10—H10A | 108.5 | C19—C20—H20B | 109.5 |
C11—C10—H10B | 108.5 | H20A—C20—H20B | 109.5 |
C9—C10—H10B | 108.5 | C19—C20—H20C | 109.5 |
H10A—C10—H10B | 107.5 | H20A—C20—H20C | 109.5 |
C12—C11—C1 | 115.7 (4) | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 117.0 (3) | C17—N1—C16 | 111.7 (4) |
C1—C11—C10 | 127.1 (4) | C17—N1—C9 | 113.5 (4) |
C11—C12—C4 | 123.2 (4) | C16—N1—C9 | 113.3 (4) |
C11—C12—C13 | 127.7 (4) | C3—O1—C18 | 117.2 (4) |
C4—C12—C13 | 109.1 (4) | C4—O2—C5 | 105.1 (3) |
C12—C13—C14 | 108.7 (4) | C19—O3—C6 | 117.3 (4) |
C12—C13—C15 | 110.4 (4) | ||
C11—C1—C2—C3 | −2.0 (8) | C10—C9—N1—C16 | 64.5 (5) |
C2—C1—C11—C10 | 174.3 (5) | C10—C9—N1—C17 | −64.4 (5) |
C2—C1—C11—C12 | −0.8 (8) | C14—C9—N1—C16 | −62.5 (4) |
C1—C2—C3—O1 | −179.1 (5) | C14—C9—N1—C17 | 168.7 (4) |
C1—C2—C3—C4 | 1.6 (7) | N1—C9—C10—C11 | −85.6 (5) |
C2—C3—O1—C18 | 2.6 (8) | C14—C9—C10—C11 | 37.8 (6) |
C4—C3—O1—C18 | −178.0 (5) | N1—C9—C14—C8 | −169.5 (4) |
O1—C3—C4—O2 | 3.4 (7) | N1—C9—C14—C13 | 66.8 (4) |
O1—C3—C4—C12 | −177.8 (4) | C10—C9—C14—C8 | 62.2 (5) |
C2—C3—C4—O2 | −177.2 (4) | C10—C9—C14—C13 | −61.5 (5) |
C2—C3—C4—C12 | 1.7 (7) | C9—C10—C11—C1 | 175.7 (4) |
C3—C4—O2—C5 | 160.7 (4) | C9—C10—C11—C12 | −9.2 (6) |
C12—C4—O2—C5 | −18.2 (5) | C1—C11—C12—C4 | 4.1 (7) |
O2—C4—C12—C11 | 174.3 (4) | C1—C11—C12—C13 | −177.6 (4) |
O2—C4—C12—C13 | −4.3 (5) | C10—C11—C12—C4 | −171.5 (4) |
C3—C4—C12—C11 | −4.7 (7) | C10—C11—C12—C13 | 6.8 (7) |
C3—C4—C12—C13 | 176.7 (4) | C4—C12—C13—C5 | 23.3 (5) |
C6—C5—O2—C4 | −89.3 (4) | C4—C12—C13—C14 | 147.6 (4) |
C13—C5—O2—C4 | 32.5 (4) | C4—C12—C13—C15 | −95.0 (5) |
O2—C5—C6—O3 | 0.8 (5) | C11—C12—C13—C5 | −155.3 (5) |
O2—C5—C6—C7 | 120.4 (4) | C11—C12—C13—C14 | −30.9 (6) |
C13—C5—C6—O3 | −114.7 (4) | C11—C12—C13—C15 | 86.5 (5) |
C13—C5—C6—C7 | 4.8 (5) | C5—C13—C14—C8 | 40.8 (5) |
O2—C5—C13—C12 | −33.0 (4) | C5—C13—C14—C9 | 166.5 (4) |
O2—C5—C13—C14 | −150.1 (4) | C12—C13—C14—C8 | −70.8 (5) |
O2—C5—C13—C15 | 83.4 (4) | C12—C13—C14—C9 | 54.9 (5) |
C6—C5—C13—C12 | 85.7 (4) | C15—C13—C14—C8 | 169.8 (4) |
C6—C5—C13—C14 | −31.3 (5) | C15—C13—C14—C9 | −64.5 (4) |
C6—C5—C13—C15 | −157.8 (4) | C5—C13—C15—C16 | −171.0 (3) |
C5—C6—O3—C19 | −76.4 (5) | C12—C13—C15—C16 | −61.7 (5) |
C7—C6—O3—C19 | 157.5 (4) | C14—C13—C15—C16 | 56.6 (5) |
O3—C6—C7—C8 | 134.4 (5) | C13—C15—C16—N1 | −51.2 (5) |
C5—C6—C7—C8 | 11.8 (7) | C15—C16—N1—C9 | 55.2 (5) |
C6—C7—C8—C14 | −1.0 (8) | C15—C16—N1—C17 | −175.1 (4) |
C7—C8—C14—C9 | −146.5 (4) | O4—C19—O3—C6 | −11.8 (7) |
C7—C8—C14—C13 | −24.8 (6) | C20—C19—O3—C6 | 166.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N1i | 0.98 | 2.42 | 3.363 (5) | 163 |
C20—H20C···Cg1ii | 0.96 | 2.52 | 3.421 (2) | 157 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+2, y+1/2, −z+1/2. |
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