Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028327/hg2071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028327/hg2071Isup2.hkl |
CCDC reference: 618224
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.187
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H25NO5 | Z = 2 |
Mr = 371.42 | F(000) = 396 |
Triclinic, P1 | Dx = 1.229 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 5.446 (3) Å | Cell parameters from 6175 reflections |
b = 10.454 (7) Å | θ = 3.3–27.5° |
c = 18.386 (12) Å | µ = 0.09 mm−1 |
α = 77.94 (3)° | T = 298 K |
β = 88.97 (2)° | Prism, orange |
γ = 78.68 (2)° | 0.4 × 0.35 × 0.12 mm |
V = 1003.5 (11) Å3 |
Rigaku R-AXIS RAPID diffractometer | Rint = 0.033 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.4° |
ω scans | h = −6→6 |
9965 measured reflections | k = −13→13 |
4536 independent reflections | l = −23→23 |
2368 reflections with I > 2σ(I) |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0923P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max < 0.001 |
wR(F2) = 0.187 | Δρmax = 0.22 e Å−3 |
S = 1.07 | Δρmin = −0.25 e Å−3 |
4536 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
253 parameters | Extinction coefficient: 0.014 (4) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.0208 (4) | 0.1852 (2) | 0.23010 (11) | 0.0643 (6) | |
O1 | 0.5302 (2) | 0.07593 (14) | 0.36235 (8) | 0.0521 (4) | |
O2 | 0.7095 (3) | 0.12529 (18) | 0.47732 (9) | 0.0683 (5) | |
O3 | 0.3671 (4) | 0.2607 (2) | 0.49970 (12) | 0.1023 (8) | |
O4 | −0.0159 (3) | 0.40111 (18) | 0.40422 (10) | 0.0791 (6) | |
O5 | −0.2237 (3) | 0.35838 (19) | 0.31329 (11) | 0.0836 (6) | |
C1 | 0.3838 (4) | 0.1723 (2) | 0.39088 (11) | 0.0507 (5) | |
C2 | 0.1744 (4) | 0.2268 (2) | 0.34706 (11) | 0.0507 (5) | |
C3 | 0.1926 (4) | 0.1574 (2) | 0.28668 (11) | 0.0509 (5) | |
C4 | 0.4148 (4) | 0.0652 (2) | 0.29842 (11) | 0.0506 (5) | |
C5 | 0.4793 (4) | 0.1939 (2) | 0.46097 (13) | 0.0563 (6) | |
C6 | 0.8236 (5) | 0.1403 (3) | 0.54386 (13) | 0.0706 (7) | |
H6A | 0.8771 | 0.2243 | 0.5349 | 0.106* | |
H6B | 0.9658 | 0.0692 | 0.5582 | 0.106* | |
H6C | 0.7044 | 0.1376 | 0.583 | 0.106* | |
C7 | −0.0411 (4) | 0.3351 (2) | 0.35261 (13) | 0.0559 (6) | |
C8 | −0.2234 (6) | 0.5063 (3) | 0.41290 (17) | 0.0906 (9) | |
H8A | −0.2561 | 0.5706 | 0.3668 | 0.136* | |
H8B | −0.1823 | 0.549 | 0.4512 | 0.136* | |
H8C | −0.3696 | 0.469 | 0.4264 | 0.136* | |
C9 | 0.0428 (4) | 0.1261 (2) | 0.16655 (12) | 0.0583 (6) | |
H9A | 0.0466 | 0.0312 | 0.1822 | 0.07* | |
H9B | 0.1989 | 0.1377 | 0.1422 | 0.07* | |
C10 | −0.1740 (4) | 0.1887 (3) | 0.11223 (13) | 0.0687 (7) | |
H10A | −0.3294 | 0.1805 | 0.1377 | 0.082* | |
H10B | −0.1734 | 0.2831 | 0.0958 | 0.082* | |
C11 | −0.1664 (6) | 0.1282 (4) | 0.04657 (17) | 0.1000 (10) | |
H11A | −0.1554 | 0.0329 | 0.0635 | 0.12* | |
H11B | −0.0147 | 0.1411 | 0.02 | 0.12* | |
C12 | −0.3835 (7) | 0.1810 (5) | −0.00650 (19) | 0.1274 (15) | |
H12A | −0.5316 | 0.1562 | 0.0166 | 0.191* | |
H12B | −0.3517 | 0.1444 | −0.0503 | 0.191* | |
H12C | −0.4072 | 0.2765 | −0.02 | 0.191* | |
C13 | 0.5398 (4) | −0.0370 (2) | 0.26238 (11) | 0.0528 (5) | |
H13 | 0.4617 | −0.0475 | 0.2201 | 0.063* | |
C14 | 0.7595 (4) | −0.1191 (2) | 0.28394 (12) | 0.0565 (6) | |
H14 | 0.8354 | −0.1089 | 0.3267 | 0.068* | |
C15 | 0.8913 (4) | −0.2224 (2) | 0.24745 (12) | 0.0548 (6) | |
C16 | 0.8000 (4) | −0.2538 (3) | 0.18531 (14) | 0.0719 (7) | |
H16 | 0.6446 | −0.2076 | 0.165 | 0.086* | |
C17 | 0.9335 (5) | −0.3520 (3) | 0.15284 (16) | 0.0801 (8) | |
H17 | 0.8673 | −0.3693 | 0.1105 | 0.096* | |
C18 | 1.1616 (5) | −0.4252 (2) | 0.18099 (16) | 0.0700 (7) | |
C19 | 1.2527 (5) | −0.3964 (3) | 0.24272 (18) | 0.0824 (8) | |
H19 | 1.4058 | −0.4451 | 0.2635 | 0.099* | |
C20 | 1.1226 (4) | −0.2963 (3) | 0.27523 (16) | 0.0764 (8) | |
H20 | 1.1921 | −0.278 | 0.3168 | 0.092* | |
C21 | 1.3072 (6) | −0.5352 (3) | 0.1462 (2) | 0.1036 (11) | |
H21A | 1.4771 | −0.5234 | 0.1393 | 0.155* | |
H21B | 1.2316 | −0.5318 | 0.0988 | 0.155* | |
H21C | 1.3052 | −0.6202 | 0.1782 | 0.155* | |
H1 | −0.111 (5) | 0.243 (3) | 0.2379 (14) | 0.085 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0552 (11) | 0.0757 (14) | 0.0579 (11) | 0.0121 (10) | −0.0141 (9) | −0.0269 (10) |
O1 | 0.0476 (7) | 0.0555 (9) | 0.0527 (8) | 0.0011 (6) | −0.0023 (6) | −0.0204 (7) |
O2 | 0.0566 (9) | 0.0863 (12) | 0.0589 (9) | 0.0073 (8) | −0.0134 (7) | −0.0270 (8) |
O3 | 0.0809 (12) | 0.1262 (18) | 0.1041 (15) | 0.0303 (11) | −0.0237 (10) | −0.0792 (14) |
O4 | 0.0841 (11) | 0.0669 (11) | 0.0794 (12) | 0.0234 (9) | −0.0128 (9) | −0.0343 (9) |
O5 | 0.0583 (9) | 0.0871 (13) | 0.1023 (14) | 0.0191 (9) | −0.0205 (9) | −0.0421 (11) |
C1 | 0.0491 (11) | 0.0509 (12) | 0.0520 (12) | −0.0028 (9) | 0.0007 (9) | −0.0167 (10) |
C2 | 0.0465 (11) | 0.0524 (13) | 0.0523 (12) | −0.0029 (9) | 0.0005 (9) | −0.0152 (10) |
C3 | 0.0481 (11) | 0.0521 (12) | 0.0510 (12) | −0.0017 (9) | −0.0003 (9) | −0.0149 (10) |
C4 | 0.0479 (10) | 0.0584 (13) | 0.0439 (11) | −0.0024 (9) | −0.0045 (9) | −0.0143 (9) |
C5 | 0.0510 (11) | 0.0607 (14) | 0.0603 (13) | −0.0061 (10) | −0.0025 (10) | −0.0241 (11) |
C6 | 0.0686 (14) | 0.0851 (18) | 0.0582 (14) | −0.0101 (12) | −0.0135 (11) | −0.0188 (13) |
C7 | 0.0522 (12) | 0.0534 (13) | 0.0585 (13) | 0.0002 (9) | −0.0001 (10) | −0.0135 (11) |
C8 | 0.096 (2) | 0.0718 (18) | 0.092 (2) | 0.0285 (15) | −0.0021 (16) | −0.0325 (15) |
C9 | 0.0530 (11) | 0.0654 (14) | 0.0547 (13) | −0.0017 (10) | −0.0062 (10) | −0.0169 (11) |
C10 | 0.0587 (13) | 0.0840 (18) | 0.0608 (14) | −0.0008 (12) | −0.0079 (11) | −0.0210 (13) |
C11 | 0.094 (2) | 0.134 (3) | 0.0739 (19) | −0.0046 (18) | −0.0197 (15) | −0.0394 (19) |
C12 | 0.110 (3) | 0.197 (4) | 0.075 (2) | −0.034 (3) | −0.0369 (19) | −0.022 (2) |
C13 | 0.0524 (11) | 0.0574 (13) | 0.0472 (11) | −0.0007 (9) | −0.0043 (9) | −0.0166 (10) |
C14 | 0.0550 (11) | 0.0575 (13) | 0.0562 (13) | 0.0003 (10) | −0.0073 (10) | −0.0199 (10) |
C15 | 0.0485 (11) | 0.0553 (13) | 0.0579 (13) | 0.0008 (9) | −0.0050 (10) | −0.0156 (10) |
C16 | 0.0628 (13) | 0.0747 (17) | 0.0757 (17) | 0.0115 (12) | −0.0140 (12) | −0.0323 (14) |
C17 | 0.0778 (16) | 0.0861 (19) | 0.0797 (18) | 0.0029 (14) | −0.0043 (14) | −0.0423 (15) |
C18 | 0.0637 (14) | 0.0540 (14) | 0.0904 (19) | −0.0006 (11) | 0.0140 (13) | −0.0220 (13) |
C19 | 0.0566 (13) | 0.0745 (18) | 0.108 (2) | 0.0155 (12) | −0.0076 (14) | −0.0275 (16) |
C20 | 0.0578 (13) | 0.0798 (18) | 0.0873 (18) | 0.0142 (12) | −0.0179 (12) | −0.0324 (15) |
C21 | 0.100 (2) | 0.076 (2) | 0.139 (3) | −0.0017 (16) | 0.032 (2) | −0.0466 (19) |
N1—C3 | 1.358 (3) | C10—H10A | 0.97 |
N1—C9 | 1.424 (3) | C10—H10B | 0.97 |
N1—H1 | 0.87 (3) | C11—C12 | 1.488 (4) |
O1—C1 | 1.348 (2) | C11—H11A | 0.97 |
O1—C4 | 1.378 (3) | C11—H11B | 0.97 |
O2—C5 | 1.322 (3) | C12—H12A | 0.96 |
O2—C6 | 1.433 (3) | C12—H12B | 0.96 |
O3—C5 | 1.180 (3) | C12—H12C | 0.96 |
O4—C7 | 1.308 (3) | C13—C14 | 1.340 (3) |
O4—C8 | 1.446 (3) | C13—H13 | 0.93 |
O5—C7 | 1.195 (3) | C14—C15 | 1.454 (3) |
C1—C2 | 1.364 (3) | C14—H14 | 0.93 |
C1—C5 | 1.474 (3) | C15—C16 | 1.379 (3) |
C2—C3 | 1.439 (3) | C15—C20 | 1.386 (3) |
C2—C7 | 1.481 (3) | C16—C17 | 1.373 (3) |
C3—C4 | 1.380 (3) | C16—H16 | 0.93 |
C4—C13 | 1.427 (3) | C17—C18 | 1.372 (4) |
C6—H6A | 0.96 | C17—H17 | 0.93 |
C6—H6B | 0.96 | C18—C19 | 1.359 (4) |
C6—H6C | 0.96 | C18—C21 | 1.514 (4) |
C8—H8A | 0.96 | C19—C20 | 1.382 (4) |
C8—H8B | 0.96 | C19—H19 | 0.93 |
C8—H8C | 0.96 | C20—H20 | 0.93 |
C9—C10 | 1.512 (3) | C21—H21A | 0.96 |
C9—H9A | 0.97 | C21—H21B | 0.96 |
C9—H9B | 0.97 | C21—H21C | 0.96 |
C10—C11 | 1.472 (4) | ||
C3—N1—C9 | 125.54 (19) | C11—C10—H10B | 108.9 |
C3—N1—H1 | 111.4 (18) | C9—C10—H10B | 108.9 |
C9—N1—H1 | 123.0 (19) | H10A—C10—H10B | 107.7 |
C1—O1—C4 | 108.35 (16) | C10—C11—C12 | 115.6 (3) |
C5—O2—C6 | 116.41 (19) | C10—C11—H11A | 108.4 |
C7—O4—C8 | 116.8 (2) | C12—C11—H11A | 108.4 |
O1—C1—C2 | 110.34 (19) | C10—C11—H11B | 108.4 |
O1—C1—C5 | 114.98 (18) | C12—C11—H11B | 108.4 |
C2—C1—C5 | 134.67 (19) | H11A—C11—H11B | 107.4 |
C1—C2—C3 | 106.37 (18) | C11—C12—H12A | 109.5 |
C1—C2—C7 | 132.0 (2) | C11—C12—H12B | 109.5 |
C3—C2—C7 | 121.59 (19) | H12A—C12—H12B | 109.5 |
N1—C3—C4 | 129.6 (2) | C11—C12—H12C | 109.5 |
N1—C3—C2 | 124.13 (18) | H12A—C12—H12C | 109.5 |
C4—C3—C2 | 106.24 (19) | H12B—C12—H12C | 109.5 |
O1—C4—C3 | 108.70 (18) | C14—C13—C4 | 126.0 (2) |
O1—C4—C13 | 115.90 (17) | C14—C13—H13 | 117 |
C3—C4—C13 | 135.3 (2) | C4—C13—H13 | 117 |
O3—C5—O2 | 122.8 (2) | C13—C14—C15 | 126.8 (2) |
O3—C5—C1 | 125.7 (2) | C13—C14—H14 | 116.6 |
O2—C5—C1 | 111.43 (19) | C15—C14—H14 | 116.6 |
O2—C6—H6A | 109.5 | C16—C15—C20 | 116.2 (2) |
O2—C6—H6B | 109.5 | C16—C15—C14 | 123.9 (2) |
H6A—C6—H6B | 109.5 | C20—C15—C14 | 119.9 (2) |
O2—C6—H6C | 109.5 | C17—C16—C15 | 121.4 (2) |
H6A—C6—H6C | 109.5 | C17—C16—H16 | 119.3 |
H6B—C6—H6C | 109.5 | C15—C16—H16 | 119.3 |
O5—C7—O4 | 123.3 (2) | C18—C17—C16 | 122.0 (3) |
O5—C7—C2 | 122.1 (2) | C18—C17—H17 | 119 |
O4—C7—C2 | 114.7 (2) | C16—C17—H17 | 119 |
O4—C8—H8A | 109.5 | C19—C18—C17 | 117.2 (2) |
O4—C8—H8B | 109.5 | C19—C18—C21 | 120.6 (3) |
H8A—C8—H8B | 109.5 | C17—C18—C21 | 122.2 (3) |
O4—C8—H8C | 109.5 | C18—C19—C20 | 121.4 (2) |
H8A—C8—H8C | 109.5 | C18—C19—H19 | 119.3 |
H8B—C8—H8C | 109.5 | C20—C19—H19 | 119.3 |
N1—C9—C10 | 110.97 (19) | C19—C20—C15 | 121.7 (3) |
N1—C9—H9A | 109.4 | C19—C20—H20 | 119.1 |
C10—C9—H9A | 109.4 | C15—C20—H20 | 119.1 |
N1—C9—H9B | 109.4 | C18—C21—H21A | 109.5 |
C10—C9—H9B | 109.4 | C18—C21—H21B | 109.5 |
H9A—C9—H9B | 108 | H21A—C21—H21B | 109.5 |
C11—C10—C9 | 113.5 (2) | C18—C21—H21C | 109.5 |
C11—C10—H10A | 108.9 | H21A—C21—H21C | 109.5 |
C9—C10—H10A | 108.9 | H21B—C21—H21C | 109.5 |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register