Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038419/bh6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038419/bh6051Isup2.hkl |
CCDC reference: 293827
Key indicators
- Single-crystal X-ray study
- T = 287 K
- Mean (C-C)= 0.003 Å
- R factor = 0.040
- wR factor = 0.121
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: DREAR (Blessing, 1987); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Bruno et al., 2002) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
C25H23NO5 | F(000) = 880 |
Mr = 417.44 | Dx = 1.306 Mg m−3 |
Monoclinic, P21/c | Melting point: 451 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.785 (5) Å | Cell parameters from 25 reflections |
b = 10.357 (2) Å | θ = 7.5–21.8° |
c = 13.502 (1) Å | µ = 0.09 mm−1 |
β = 105.96 (2)° | T = 287 K |
V = 2122.2 (8) Å3 | Rhomboid, red-orange |
Z = 4 | 0.3 × 0.2 × 0.2 mm |
Enraf–Nonius MACH3 diffractometer | Rint = 0.011 |
Radiation source: fine-focus sealed tube | θmax = 25.3°, θmin = 1.3° |
Graphite monochromator | h = −18→18 |
ω/2θ scans | k = −12→4 |
4890 measured reflections | l = −16→0 |
3880 independent reflections | 3 standard reflections every 60 min |
2320 reflections with I > 2σ(I) | intensity decay: 1.5% |
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)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.121 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.3937P] where P = (Fo2 + 2Fc2)/3 |
3880 reflections | (Δ/σ)max < 0.001 |
372 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | ||
O46 | 0.31193 (9) | 0.92938 (13) | 0.77035 (10) | 0.0556 (4) | |
O42 | 0.21210 (9) | 0.57320 (14) | 0.55387 (11) | 0.0612 (4) | |
O44 | 0.47551 (10) | 0.80455 (17) | 0.54253 (12) | 0.0739 (5) | |
C41 | 0.26307 (12) | 0.74666 (18) | 0.66547 (13) | 0.0433 (4) | |
C4 | −0.18582 (13) | 0.6229 (2) | 1.09063 (15) | 0.0507 (5) | |
C42 | 0.27383 (12) | 0.66837 (19) | 0.58474 (14) | 0.0471 (4) | |
C24 | 0.06833 (12) | 0.63745 (18) | 0.76996 (14) | 0.0469 (5) | |
C44 | 0.40338 (13) | 0.7806 (2) | 0.57725 (15) | 0.0531 (5) | |
C46 | 0.32509 (12) | 0.84750 (19) | 0.69592 (13) | 0.0458 (5) | |
N1 | −0.37402 (14) | 0.5676 (2) | 1.25683 (16) | 0.0733 (6) | |
C21 | −0.05229 (12) | 0.60648 (19) | 0.89040 (15) | 0.0484 (5) | |
C1 | −0.30872 (14) | 0.5884 (2) | 1.19953 (17) | 0.0580 (6) | |
C27 | 0.12820 (13) | 0.6498 (2) | 0.70529 (15) | 0.0498 (5) | |
C45 | 0.39434 (13) | 0.8636 (2) | 0.65373 (15) | 0.0521 (5) | |
C26 | 0.01835 (14) | 0.6922 (2) | 0.91974 (16) | 0.0547 (5) | |
O1 | −0.42445 (12) | 0.4753 (2) | 1.23247 (16) | 0.0883 (6) | |
C28 | 0.19698 (13) | 0.7287 (2) | 0.72155 (15) | 0.0475 (5) | |
C8 | −0.11775 (13) | 0.5883 (2) | 0.94735 (16) | 0.0521 (5) | |
C43 | 0.34257 (13) | 0.6847 (2) | 0.54037 (15) | 0.0518 (5) | |
C22 | −0.06000 (13) | 0.5351 (2) | 0.80089 (16) | 0.0536 (5) | |
C23 | −0.00161 (14) | 0.5501 (2) | 0.74276 (16) | 0.0527 (5) | |
C5 | −0.17465 (15) | 0.6787 (2) | 1.18674 (17) | 0.0591 (6) | |
C7 | −0.11897 (14) | 0.6430 (2) | 1.03552 (16) | 0.0523 (5) | |
C25 | 0.07664 (14) | 0.7069 (2) | 0.86104 (16) | 0.0549 (5) | |
O2 | −0.37513 (14) | 0.6428 (2) | 1.32600 (15) | 0.1036 (7) | |
C2 | −0.32233 (16) | 0.5307 (3) | 1.10489 (19) | 0.0694 (7) | |
C6 | −0.23589 (16) | 0.6630 (2) | 1.24115 (18) | 0.0652 (6) | |
C3 | −0.26102 (15) | 0.5491 (3) | 1.05150 (18) | 0.0686 (7) | |
C56 | 0.3666 (2) | 1.0413 (3) | 0.7947 (2) | 0.0675 (6) | |
C52 | 0.22186 (19) | 0.4812 (3) | 0.47907 (19) | 0.0651 (6) | |
C54 | 0.4886 (2) | 0.7279 (4) | 0.4609 (2) | 0.0815 (8) | |
H28 | 0.2061 (13) | 0.780 (2) | 0.7816 (16) | 0.061 (6)* | |
H43 | 0.3493 (13) | 0.631 (2) | 0.4901 (16) | 0.057 (6)* | |
H8 | −0.1649 (13) | 0.529 (2) | 0.9156 (16) | 0.057 (6)* | |
H45 | 0.4374 (14) | 0.931 (2) | 0.6744 (16) | 0.062 (6)* | |
H23 | −0.0094 (13) | 0.496 (2) | 0.6817 (16) | 0.061 (6)* | |
H7 | −0.0725 (15) | 0.702 (2) | 1.0698 (16) | 0.065 (6)* | |
H6 | −0.2269 (16) | 0.699 (2) | 1.3036 (19) | 0.082 (8)* | |
H22 | −0.1093 (14) | 0.475 (2) | 0.7784 (16) | 0.064 (6)* | |
H561 | 0.3436 (14) | 1.095 (2) | 0.8414 (19) | 0.077 (7)* | |
H27 | 0.1151 (13) | 0.596 (2) | 0.6478 (16) | 0.060 (6)* | |
H562 | 0.4294 (17) | 1.018 (2) | 0.8249 (18) | 0.078 (8)* | |
H541 | 0.4397 (17) | 0.742 (2) | 0.399 (2) | 0.081 (8)* | |
H563 | 0.3602 (16) | 1.097 (2) | 0.733 (2) | 0.088 (8)* | |
H25 | 0.1242 (15) | 0.763 (2) | 0.8854 (16) | 0.066 (6)* | |
H26 | 0.0284 (14) | 0.746 (2) | 0.9807 (18) | 0.076 (7)* | |
H3 | −0.2716 (16) | 0.511 (2) | 0.986 (2) | 0.090 (8)* | |
H521 | 0.2789 (16) | 0.430 (2) | 0.5044 (18) | 0.075 (7)* | |
H5 | −0.1220 (16) | 0.728 (2) | 1.2156 (18) | 0.081 (8)* | |
H522 | 0.1716 (17) | 0.418 (3) | 0.4716 (19) | 0.087 (8)* | |
H543 | 0.5401 (18) | 0.761 (3) | 0.4507 (19) | 0.091 (8)* | |
H2 | −0.3763 (18) | 0.482 (3) | 1.077 (2) | 0.093 (8)* | |
H523 | 0.2184 (16) | 0.524 (2) | 0.417 (2) | 0.081 (8)* | |
H542 | 0.4932 (18) | 0.630 (3) | 0.478 (2) | 0.096 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O46 | 0.0598 (8) | 0.0598 (9) | 0.0539 (8) | −0.0076 (7) | 0.0267 (7) | −0.0105 (7) |
O42 | 0.0695 (9) | 0.0630 (9) | 0.0582 (8) | −0.0119 (8) | 0.0294 (7) | −0.0153 (7) |
O44 | 0.0606 (9) | 0.1017 (13) | 0.0721 (10) | −0.0155 (9) | 0.0396 (8) | −0.0250 (9) |
C41 | 0.0431 (10) | 0.0493 (11) | 0.0384 (9) | 0.0056 (9) | 0.0126 (8) | 0.0037 (8) |
C4 | 0.0484 (11) | 0.0558 (12) | 0.0491 (11) | 0.0036 (9) | 0.0156 (9) | 0.0035 (9) |
C42 | 0.0485 (10) | 0.0499 (11) | 0.0428 (10) | 0.0007 (9) | 0.0126 (8) | 0.0016 (9) |
C24 | 0.0476 (10) | 0.0462 (11) | 0.0478 (10) | 0.0044 (9) | 0.0145 (8) | 0.0037 (9) |
C44 | 0.0464 (11) | 0.0698 (14) | 0.0469 (11) | 0.0001 (10) | 0.0191 (9) | −0.0008 (10) |
C46 | 0.0460 (10) | 0.0533 (12) | 0.0383 (9) | 0.0062 (9) | 0.0116 (8) | −0.0002 (9) |
N1 | 0.0649 (13) | 0.0932 (16) | 0.0709 (13) | 0.0313 (12) | 0.0341 (11) | 0.0292 (13) |
C21 | 0.0443 (10) | 0.0522 (11) | 0.0498 (11) | 0.0010 (9) | 0.0149 (9) | 0.0068 (9) |
C1 | 0.0514 (12) | 0.0682 (14) | 0.0607 (13) | 0.0164 (11) | 0.0258 (10) | 0.0147 (11) |
C27 | 0.0496 (11) | 0.0549 (12) | 0.0466 (11) | 0.0013 (10) | 0.0160 (9) | 0.0000 (10) |
C45 | 0.0470 (11) | 0.0630 (13) | 0.0471 (11) | −0.0040 (10) | 0.0143 (9) | −0.0028 (10) |
C26 | 0.0578 (12) | 0.0601 (13) | 0.0496 (11) | −0.0056 (10) | 0.0205 (10) | −0.0047 (10) |
O1 | 0.0676 (11) | 0.1025 (15) | 0.1066 (14) | 0.0156 (10) | 0.0441 (11) | 0.0390 (12) |
C28 | 0.0498 (11) | 0.0503 (11) | 0.0459 (11) | 0.0064 (9) | 0.0187 (9) | 0.0026 (9) |
C8 | 0.0458 (11) | 0.0578 (13) | 0.0533 (12) | −0.0015 (10) | 0.0148 (9) | 0.0034 (10) |
C43 | 0.0549 (12) | 0.0612 (13) | 0.0431 (10) | 0.0026 (10) | 0.0197 (9) | −0.0041 (10) |
C22 | 0.0475 (11) | 0.0592 (13) | 0.0547 (12) | −0.0084 (10) | 0.0150 (9) | −0.0027 (10) |
C23 | 0.0523 (11) | 0.0573 (13) | 0.0492 (11) | −0.0043 (10) | 0.0155 (9) | −0.0065 (10) |
C5 | 0.0600 (13) | 0.0626 (14) | 0.0574 (12) | −0.0021 (11) | 0.0209 (11) | −0.0087 (11) |
C7 | 0.0504 (11) | 0.0551 (13) | 0.0533 (12) | −0.0002 (10) | 0.0171 (10) | 0.0023 (10) |
C25 | 0.0533 (12) | 0.0570 (13) | 0.0575 (12) | −0.0119 (10) | 0.0204 (10) | −0.0035 (11) |
O2 | 0.1112 (15) | 0.1366 (18) | 0.0825 (12) | 0.0399 (13) | 0.0596 (12) | 0.0072 (13) |
C2 | 0.0543 (13) | 0.0911 (19) | 0.0663 (14) | −0.0115 (13) | 0.0227 (12) | −0.0061 (13) |
C6 | 0.0740 (15) | 0.0709 (16) | 0.0552 (13) | 0.0093 (13) | 0.0252 (12) | −0.0060 (12) |
C3 | 0.0601 (14) | 0.0951 (19) | 0.0543 (13) | −0.0133 (13) | 0.0221 (11) | −0.0149 (13) |
C56 | 0.0804 (18) | 0.0602 (15) | 0.0699 (16) | −0.0110 (13) | 0.0340 (14) | −0.0132 (13) |
C52 | 0.0784 (17) | 0.0646 (15) | 0.0558 (14) | −0.0079 (14) | 0.0244 (13) | −0.0136 (12) |
C54 | 0.0761 (19) | 0.106 (3) | 0.0778 (18) | −0.0081 (18) | 0.0461 (17) | −0.0240 (18) |
C4—C7 | 1.464 (3) | C1—C6 | 1.371 (3) |
C7—C8 | 1.324 (3) | C1—C2 | 1.373 (3) |
C8—C21 | 1.460 (3) | C27—H27 | 0.93 (2) |
C21—C22 | 1.393 (3) | C45—H45 | 0.96 (2) |
C22—C23 | 1.374 (3) | C26—C25 | 1.378 (3) |
C23—C24 | 1.396 (3) | C26—H26 | 0.97 (2) |
C24—C27 | 1.458 (3) | C28—H28 | 0.95 (2) |
C27—C28 | 1.328 (3) | C8—H8 | 0.97 (2) |
C28—C41 | 1.460 (3) | C43—H43 | 0.91 (2) |
O46—C46 | 1.374 (2) | C22—H22 | 0.98 (2) |
O46—C56 | 1.428 (3) | C23—H23 | 0.98 (2) |
O42—C42 | 1.368 (2) | C5—C6 | 1.375 (3) |
O42—C52 | 1.428 (3) | C5—H5 | 0.96 (2) |
O44—C44 | 1.368 (2) | C7—H7 | 0.97 (2) |
O44—C54 | 1.419 (3) | C25—H25 | 0.93 (2) |
C41—C42 | 1.406 (3) | C2—C3 | 1.370 (3) |
C41—C46 | 1.413 (3) | C2—H2 | 0.98 (3) |
C4—C5 | 1.387 (3) | C6—H6 | 0.90 (2) |
C4—C3 | 1.388 (3) | C3—H3 | 0.94 (3) |
C42—C43 | 1.387 (3) | C56—H561 | 0.98 (2) |
C24—C25 | 1.399 (3) | C56—H562 | 0.99 (2) |
C44—C43 | 1.375 (3) | C56—H563 | 1.00 (3) |
C44—C45 | 1.381 (3) | C52—H521 | 1.02 (2) |
C46—C45 | 1.375 (3) | C52—H522 | 1.01 (3) |
N1—O2 | 1.220 (3) | C52—H523 | 0.94 (3) |
N1—O1 | 1.230 (3) | C54—H541 | 0.98 (3) |
N1—C1 | 1.465 (3) | C54—H543 | 0.93 (3) |
C21—C26 | 1.395 (3) | C54—H542 | 1.04 (3) |
C46—O46—C56 | 117.78 (16) | C44—C43—C42 | 118.88 (19) |
C42—O42—C52 | 119.36 (17) | C44—C43—H43 | 120.1 (13) |
C44—O44—C54 | 118.5 (2) | C42—C43—H43 | 120.9 (13) |
C42—C41—C46 | 115.47 (16) | C23—C22—C21 | 121.6 (2) |
C42—C41—C28 | 125.80 (18) | C23—C22—H22 | 119.8 (13) |
C46—C41—C28 | 118.68 (17) | C21—C22—H22 | 118.7 (12) |
C5—C4—C3 | 117.45 (19) | C22—C23—C24 | 122.0 (2) |
C5—C4—C7 | 119.5 (2) | C22—C23—H23 | 117.9 (12) |
C3—C4—C7 | 123.07 (19) | C24—C23—H23 | 120.1 (12) |
O42—C42—C43 | 122.20 (18) | C6—C5—C4 | 121.6 (2) |
O42—C42—C41 | 115.09 (16) | C6—C5—H5 | 120.2 (14) |
C43—C42—C41 | 122.70 (19) | C4—C5—H5 | 118.3 (14) |
C23—C24—C25 | 116.14 (18) | C8—C7—C4 | 125.9 (2) |
C23—C24—C27 | 119.70 (18) | C8—C7—H7 | 120.3 (13) |
C25—C24—C27 | 124.15 (18) | C4—C7—H7 | 113.8 (13) |
O44—C44—C43 | 124.81 (18) | C26—C25—C24 | 122.2 (2) |
O44—C44—C45 | 114.21 (19) | C26—C25—H25 | 117.7 (13) |
C43—C44—C45 | 120.97 (18) | C24—C25—H25 | 120.1 (13) |
O46—C46—C45 | 121.72 (18) | C3—C2—C1 | 118.5 (2) |
O46—C46—C41 | 115.91 (15) | C3—C2—H2 | 122.3 (15) |
C45—C46—C41 | 122.37 (18) | C1—C2—H2 | 119.2 (15) |
O2—N1—O1 | 123.8 (2) | C1—C6—C5 | 118.8 (2) |
O2—N1—C1 | 118.1 (3) | C1—C6—H6 | 121.3 (16) |
O1—N1—C1 | 118.1 (2) | C5—C6—H6 | 119.9 (16) |
C22—C21—C26 | 117.15 (18) | C2—C3—C4 | 122.0 (2) |
C22—C21—C8 | 118.88 (19) | C2—C3—H3 | 117.8 (16) |
C26—C21—C8 | 123.97 (19) | C4—C3—H3 | 120.2 (16) |
C6—C1—C2 | 121.7 (2) | O46—C56—H561 | 107.7 (14) |
C6—C1—N1 | 119.9 (2) | O46—C56—H562 | 111.6 (14) |
C2—C1—N1 | 118.4 (2) | H561—C56—H562 | 112.3 (19) |
C28—C27—C24 | 126.2 (2) | O46—C56—H563 | 111.1 (15) |
C28—C27—H27 | 119.2 (13) | H561—C56—H563 | 104 (2) |
C24—C27—H27 | 114.6 (13) | H562—C56—H563 | 110 (2) |
C46—C45—C44 | 119.5 (2) | O42—C52—H521 | 111.6 (13) |
C46—C45—H45 | 123.1 (12) | O42—C52—H522 | 105.5 (14) |
C44—C45—H45 | 117.4 (12) | H521—C52—H522 | 106.9 (19) |
C25—C26—C21 | 121.0 (2) | O42—C52—H523 | 109.1 (15) |
C25—C26—H26 | 116.5 (14) | H521—C52—H523 | 112 (2) |
C21—C26—H26 | 122.5 (13) | H522—C52—H523 | 111 (2) |
C27—C28—C41 | 131.4 (2) | O44—C54—H541 | 109.3 (15) |
C27—C28—H28 | 114.3 (12) | O44—C54—H543 | 103.1 (17) |
C41—C28—H28 | 114.3 (12) | H541—C54—H543 | 109 (2) |
C7—C8—C21 | 127.3 (2) | O44—C54—H542 | 113.3 (15) |
C7—C8—H8 | 118.0 (12) | H541—C54—H542 | 109 (2) |
C21—C8—H8 | 114.7 (12) | H543—C54—H542 | 113 (2) |
C52—O42—C42—C43 | 4.9 (3) | C46—C41—C28—C27 | 174.4 (2) |
C52—O42—C42—C41 | −174.23 (19) | C22—C21—C8—C7 | 176.9 (2) |
C46—C41—C42—O42 | −178.30 (16) | C26—C21—C8—C7 | −3.4 (3) |
C28—C41—C42—O42 | 4.5 (3) | O44—C44—C43—C42 | 178.0 (2) |
C46—C41—C42—C43 | 2.6 (3) | C45—C44—C43—C42 | −3.1 (3) |
C28—C41—C42—C43 | −174.63 (19) | O42—C42—C43—C44 | −178.39 (18) |
C54—O44—C44—C43 | 1.5 (4) | C41—C42—C43—C44 | 0.6 (3) |
C54—O44—C44—C45 | −177.4 (2) | C26—C21—C22—C23 | −1.2 (3) |
C56—O46—C46—C45 | 7.0 (3) | C8—C21—C22—C23 | 178.51 (19) |
C56—O46—C46—C41 | −172.7 (2) | C21—C22—C23—C24 | −0.1 (3) |
C42—C41—C46—O46 | 176.13 (16) | C25—C24—C23—C22 | 1.3 (3) |
C28—C41—C46—O46 | −6.4 (2) | C27—C24—C23—C22 | −179.79 (19) |
C42—C41—C46—C45 | −3.6 (3) | C3—C4—C5—C6 | −0.6 (3) |
C28—C41—C46—C45 | 173.82 (18) | C7—C4—C5—C6 | 179.7 (2) |
O2—N1—C1—C6 | 19.3 (3) | C21—C8—C7—C4 | 179.88 (19) |
O1—N1—C1—C6 | −160.6 (2) | C5—C4—C7—C8 | 174.7 (2) |
O2—N1—C1—C2 | −161.2 (2) | C3—C4—C7—C8 | −5.0 (4) |
O1—N1—C1—C2 | 18.8 (3) | C21—C26—C25—C24 | 0.0 (3) |
C23—C24—C27—C28 | 179.8 (2) | C23—C24—C25—C26 | −1.2 (3) |
C25—C24—C27—C28 | −1.4 (3) | C27—C24—C25—C26 | 179.9 (2) |
O46—C46—C45—C44 | −178.37 (18) | C6—C1—C2—C3 | 0.0 (4) |
C41—C46—C45—C44 | 1.4 (3) | N1—C1—C2—C3 | −179.5 (2) |
O44—C44—C45—C46 | −178.88 (18) | C2—C1—C6—C5 | −0.8 (3) |
C43—C44—C45—C46 | 2.1 (3) | N1—C1—C6—C5 | 178.6 (2) |
C22—C21—C26—C25 | 1.3 (3) | C4—C5—C6—C1 | 1.2 (3) |
C8—C21—C26—C25 | −178.4 (2) | C1—C2—C3—C4 | 0.6 (4) |
C24—C27—C28—C41 | 177.42 (19) | C5—C4—C3—C2 | −0.3 (4) |
C42—C41—C28—C27 | −8.5 (3) | C7—C4—C3—C2 | 179.4 (2) |
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