Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006470/ya6154sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006470/ya6154Isup2.hkl |
CCDC reference: 209985
Key indicators
- Single-crystal X-ray study
- T = 168 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.084
- Data-to-parameter ratio = 7.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.50 From the CIF: _reflns_number_total 2493 Count of symmetry unique reflns 2547 Completeness (_total/calc) 97.88% 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 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.
The title alkaloid was isolated from the leaves of Kopsia fruticosa (Ker.) A. DC. (Kam et al., 2001), and crystals were grown from its ether solution.
Refinement of the Flack parameter (Flack & Schwarzenbach, 1988) was suppressed by the MERG 4 command in SHELXL97 (Sheldrick, 1997) as the lack of anomalous scatterers did not allow for the absolute configuration to be determined from the X-ray measurements. The absolute configuration was taken as reported in the solution NMR study of the compound (Kam et al., 2001). That study had assumed the configuration to be that of a structurally related compound, meloscine (Bernauer et al., 1969), whose absolute configuration was determined from the X-ray structure of the brominated derivative (Oberha¨nsli, 1969). The C-bound H atoms were positioned geometrically, and were allowed to ride on their parent atoms [Uiso(H) = 1.2Ueq(C) for the aromatic, methylene and methine C atoms, and 1.5Ueq(C) for the methyl C atoms]. The hydroxyl H atom was located and refined [O9—H1o = 0.80 (4) Å].
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
C25H28N2O9 | F(000) = 1056 |
Mr = 500.49 | Dx = 1.450 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
a = 29.005 (2) Å | Cell parameters from 5856 reflections |
b = 8.5430 (6) Å | θ = 2.2–26.5° |
c = 9.3081 (7) Å | µ = 0.11 mm−1 |
β = 96.163 (1)° | T = 168 K |
V = 2293.1 (3) Å3 | Plate, colorless |
Z = 4 | 0.50 × 0.16 × 0.14 mm |
Bruker AXS CCD area-detector diffractometer | 2173 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 26.5°, θmin = 2.2° |
ω scans | h = −35→36 |
15060 measured reflections | k = −10→5 |
2493 independent reflections | l = −11→11 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.061P)2] where P = (Fo2 + 2Fc2)/3 |
2493 reflections | (Δ/σ)max = 0.001 |
329 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.18 e Å−3 |
C25H28N2O9 | V = 2293.1 (3) Å3 |
Mr = 500.49 | Z = 4 |
Monoclinic, C2 | Mo Kα radiation |
a = 29.005 (2) Å | µ = 0.11 mm−1 |
b = 8.5430 (6) Å | T = 168 K |
c = 9.3081 (7) Å | 0.50 × 0.16 × 0.14 mm |
β = 96.163 (1)° |
Bruker AXS CCD area-detector diffractometer | 2173 reflections with I > 2σ(I) |
15060 measured reflections | Rint = 0.039 |
2493 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 1 restraint |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.20 e Å−3 |
2493 reflections | Δρmin = −0.18 e Å−3 |
329 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1925 (1) | 0.5001 (2) | 0.1924 (2) | 0.030 (1) | |
O2 | 0.2132 (1) | 0.7325 (2) | 0.1080 (2) | 0.033 (1) | |
O3 | 0.2199 (1) | 0.8567 (3) | 0.4023 (2) | 0.037 (1) | |
O4 | 0.2141 (1) | 1.0595 (3) | 0.2515 (3) | 0.054 (1) | |
O5 | 0.1349 (1) | 1.2190 (2) | 0.7433 (2) | 0.035 (1) | |
O6 | 0.1472 (1) | 0.9758 (2) | 0.8187 (2) | 0.032 (1) | |
O7 | 0.1051 (1) | 0.4502 (3) | 0.0505 (2) | 0.041 (1) | |
O8 | 0.0415 (1) | 0.3113 (3) | 0.1143 (2) | 0.046 (1) | |
O9 | 0.1320 (1) | 0.9547 (2) | 0.1180 (2) | 0.039 (1) | |
N1 | 0.1503 (1) | 0.7125 (3) | 0.2319 (2) | 0.024 (1) | |
N2 | 0.0793 (1) | 0.7490 (3) | 0.6923 (2) | 0.028 (1) | |
C1 | 0.2323 (1) | 0.4322 (4) | 0.1339 (3) | 0.035 (1) | |
C2 | 0.1876 (1) | 0.6517 (3) | 0.1697 (2) | 0.025 (1) | |
C3 | 0.1493 (1) | 0.8818 (3) | 0.2467 (2) | 0.027 (1) | |
C4 | 0.1984 (1) | 0.9437 (3) | 0.2959 (3) | 0.035 (1) | |
C5 | 0.2644 (1) | 0.9136 (5) | 0.4666 (4) | 0.056 (1) | |
C6 | 0.1156 (1) | 0.9272 (3) | 0.3580 (2) | 0.024 (1) | |
C7 | 0.1096 (1) | 0.8009 (3) | 0.4738 (2) | 0.022 (1) | |
C8 | 0.0894 (1) | 0.6634 (3) | 0.3871 (2) | 0.023 (1) | |
C9 | 0.1112 (1) | 0.6233 (3) | 0.2640 (2) | 0.023 (1) | |
C10 | 0.0917 (1) | 0.5058 (3) | 0.1777 (2) | 0.026 (1) | |
C11 | 0.0723 (1) | 0.3299 (4) | 0.0061 (3) | 0.050 (1) | |
C12 | 0.0533 (1) | 0.4262 (3) | 0.2140 (3) | 0.029 (1) | |
C13 | 0.0315 (1) | 0.4608 (3) | 0.3326 (3) | 0.029 (1) | |
C14 | 0.0506 (1) | 0.5817 (3) | 0.4190 (2) | 0.028 (1) | |
C15 | 0.1501 (1) | 0.7419 (3) | 0.5824 (2) | 0.024 (1) | |
C16 | 0.1245 (1) | 0.6718 (3) | 0.7036 (3) | 0.030 (1) | |
C17 | 0.0565 (1) | 0.7866 (4) | 0.8212 (3) | 0.038 (1) | |
C18 | 0.0328 (1) | 0.9398 (4) | 0.8112 (3) | 0.040 (1) | |
C19 | 0.0435 (1) | 1.0548 (4) | 0.7264 (3) | 0.035 (1) | |
C20 | 0.0828 (1) | 1.0328 (3) | 0.6324 (3) | 0.027 (1) | |
C21 | 0.0762 (1) | 0.8625 (3) | 0.5783 (2) | 0.024 (1) | |
C22 | 0.1258 (1) | 1.0671 (3) | 0.7389 (2) | 0.026 (1) | |
C23 | 0.1721 (1) | 1.2677 (3) | 0.8502 (3) | 0.038 (1) | |
C24 | 0.0823 (1) | 1.1384 (3) | 0.5005 (3) | 0.032 (1) | |
C25 | 0.1224 (1) | 1.0928 (3) | 0.4151 (3) | 0.031 (1) | |
H1o | 0.150 (1) | 0.944 (5) | 0.061 (4) | 0.06 (1)* | |
H1a | 0.2336 | 0.3198 | 0.1549 | 0.052* | |
H1b | 0.2607 | 0.4827 | 0.1783 | 0.052* | |
H1c | 0.2295 | 0.4484 | 0.0291 | 0.052* | |
H5a | 0.2768 | 0.8418 | 0.5432 | 0.084* | |
H5b | 0.2605 | 1.0178 | 0.5077 | 0.084* | |
H5c | 0.2859 | 0.9198 | 0.3925 | 0.084* | |
H6 | 0.0846 | 0.9307 | 0.2995 | 0.029* | |
H11a | 0.0546 | 0.3588 | −0.0870 | 0.060* | |
H11b | 0.0887 | 0.2302 | −0.0074 | 0.060* | |
H13 | 0.0047 | 0.4055 | 0.3547 | 0.035* | |
H14 | 0.0366 | 0.6092 | 0.5032 | 0.033* | |
H15a | 0.1687 | 0.6615 | 0.5382 | 0.029* | |
H15b | 0.1706 | 0.8291 | 0.6186 | 0.029* | |
H16a | 0.1207 | 0.5573 | 0.6908 | 0.036* | |
H16b | 0.1418 | 0.6923 | 0.7992 | 0.036* | |
H17a | 0.0800 | 0.7866 | 0.9066 | 0.046* | |
H17b | 0.0335 | 0.7039 | 0.8357 | 0.046* | |
H18 | 0.0083 | 0.9565 | 0.8696 | 0.048* | |
H19 | 0.0268 | 1.1506 | 0.7241 | 0.042* | |
H21 | 0.0442 | 0.8549 | 0.5270 | 0.029* | |
H23a | 0.1761 | 1.3814 | 0.8448 | 0.057* | |
H23b | 0.2010 | 1.2156 | 0.8313 | 0.057* | |
H23c | 0.1645 | 1.2391 | 0.9468 | 0.057* | |
H24a | 0.0856 | 1.2491 | 0.5314 | 0.038* | |
H24b | 0.0525 | 1.1270 | 0.4389 | 0.038* | |
H25a | 0.1239 | 1.1662 | 0.3335 | 0.037* | |
H25b | 0.1520 | 1.0998 | 0.4783 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.026 (1) | 0.030 (1) | 0.033 (1) | −0.001 (1) | 0.005 (1) | −0.005 (1) |
O2 | 0.029 (1) | 0.039 (1) | 0.033 (1) | −0.004 (1) | 0.012 (1) | −0.002 (1) |
O3 | 0.032 (1) | 0.051 (1) | 0.028 (1) | −0.018 (1) | 0.002 (1) | −0.006 (1) |
O4 | 0.065 (1) | 0.037 (1) | 0.065 (1) | −0.021 (1) | 0.025 (1) | −0.002 (1) |
O5 | 0.035 (1) | 0.031 (1) | 0.036 (1) | 0.002 (1) | −0.008 (1) | −0.008 (1) |
O6 | 0.034 (1) | 0.038 (1) | 0.024 (1) | 0.001 (1) | −0.005 (1) | −0.001 (1) |
O7 | 0.033 (1) | 0.057 (1) | 0.034 (1) | −0.012 (1) | 0.010 (1) | −0.026 (1) |
O8 | 0.040 (1) | 0.048 (1) | 0.051 (1) | −0.016 (1) | 0.012 (1) | −0.028 (1) |
O9 | 0.060 (1) | 0.039 (1) | 0.020 (1) | 0.006 (1) | 0.008 (1) | 0.006 (1) |
N1 | 0.026 (1) | 0.026 (1) | 0.022 (1) | −0.003 (1) | 0.005 (1) | −0.006 (1) |
N2 | 0.029 (1) | 0.037 (1) | 0.020 (1) | −0.001 (1) | 0.006 (1) | −0.002 (1) |
C1 | 0.024 (1) | 0.038 (2) | 0.043 (1) | 0.002 (1) | 0.004 (1) | −0.009 (1) |
C2 | 0.024 (1) | 0.034 (1) | 0.019 (1) | −0.004 (1) | 0.002 (1) | −0.004 (1) |
C3 | 0.037 (1) | 0.027 (1) | 0.018 (1) | −0.002 (1) | 0.004 (1) | −0.001 (1) |
C4 | 0.043 (2) | 0.031 (1) | 0.034 (1) | −0.010 (1) | 0.017 (1) | −0.010 (1) |
C5 | 0.035 (2) | 0.081 (3) | 0.053 (2) | −0.022 (2) | 0.003 (1) | −0.024 (2) |
C6 | 0.030 (1) | 0.024 (1) | 0.018 (1) | 0.002 (1) | 0.000 (1) | −0.001 (1) |
C7 | 0.022 (1) | 0.025 (1) | 0.018 (1) | 0.001 (1) | 0.003 (1) | −0.003 (1) |
C8 | 0.024 (1) | 0.024 (1) | 0.022 (1) | 0.004 (1) | 0.001 (1) | −0.001 (1) |
C9 | 0.023 (1) | 0.025 (1) | 0.020 (1) | 0.001 (1) | 0.001 (1) | −0.001 (1) |
C10 | 0.023 (1) | 0.033 (1) | 0.023 (1) | 0.004 (1) | 0.005 (1) | −0.005 (1) |
C11 | 0.045 (2) | 0.058 (2) | 0.048 (2) | −0.016 (2) | 0.012 (1) | −0.031 (2) |
C12 | 0.028 (1) | 0.027 (1) | 0.030 (1) | −0.002 (1) | −0.001 (1) | −0.009 (1) |
C13 | 0.024 (1) | 0.032 (1) | 0.034 (1) | −0.004 (1) | 0.007 (1) | −0.003 (1) |
C14 | 0.028 (1) | 0.032 (1) | 0.024 (1) | 0.000 (1) | 0.007 (1) | −0.004 (1) |
C15 | 0.025 (1) | 0.026 (1) | 0.021 (1) | 0.002 (1) | 0.001 (1) | −0.001 (1) |
C16 | 0.035 (1) | 0.032 (2) | 0.023 (1) | −0.001 (1) | 0.001 (1) | 0.001 (1) |
C17 | 0.040 (2) | 0.053 (2) | 0.024 (1) | −0.011 (1) | 0.010 (1) | −0.009 (1) |
C18 | 0.030 (1) | 0.061 (2) | 0.031 (1) | −0.002 (1) | 0.008 (1) | −0.018 (1) |
C19 | 0.026 (1) | 0.045 (2) | 0.033 (1) | 0.005 (1) | −0.002 (1) | −0.020 (1) |
C20 | 0.028 (1) | 0.032 (2) | 0.021 (1) | 0.006 (1) | −0.001 (1) | −0.007 (1) |
C21 | 0.022 (1) | 0.033 (1) | 0.019 (1) | 0.001 (1) | 0.002 (1) | −0.006 (1) |
C22 | 0.025 (1) | 0.033 (1) | 0.020 (1) | 0.004 (1) | 0.005 (1) | −0.006 (1) |
C23 | 0.031 (1) | 0.037 (2) | 0.043 (1) | −0.002 (1) | −0.008 (1) | −0.011 (1) |
C24 | 0.041 (1) | 0.027 (1) | 0.026 (1) | 0.010 (1) | −0.008 (1) | −0.006 (1) |
C25 | 0.045 (2) | 0.024 (1) | 0.023 (1) | 0.000 (1) | −0.001 (1) | −0.002 (1) |
O1—C1 | 1.449 (3) | C18—C19 | 1.319 (4) |
O1—C2 | 1.317 (3) | C19—C20 | 1.520 (3) |
O2—C2 | 1.206 (3) | C20—C21 | 1.545 (3) |
O3—C4 | 1.337 (4) | C20—C22 | 1.536 (3) |
O3—C5 | 1.447 (3) | C20—C24 | 1.523 (4) |
O4—C4 | 1.182 (3) | C24—C25 | 1.526 (4) |
O5—C22 | 1.325 (4) | O9—H1o | 0.80 (4) |
O5—C23 | 1.448 (3) | C1—H1a | 0.98 |
O6—C22 | 1.202 (3) | C1—H1b | 0.98 |
O7—C10 | 1.370 (3) | C1—H1c | 0.98 |
O7—C11 | 1.432 (3) | C5—H5a | 0.98 |
O8—C11 | 1.425 (3) | C5—H5b | 0.98 |
O8—C12 | 1.369 (3) | C5—H5c | 0.98 |
O9—C3 | 1.396 (3) | C6—H6 | 1 |
N1—C2 | 1.381 (3) | C11—H11a | 0.99 |
N1—C3 | 1.453 (3) | C11—H11b | 0.99 |
N1—C9 | 1.423 (3) | C13—H13 | 0.95 |
N2—C16 | 1.459 (3) | C14—H14 | 0.95 |
N2—C17 | 1.467 (3) | C15—H15a | 0.99 |
N2—C21 | 1.433 (3) | C15—H15b | 0.99 |
C3—C4 | 1.541 (4) | C16—H16a | 0.99 |
C3—C6 | 1.549 (3) | C16—H16b | 0.99 |
C6—C7 | 1.548 (3) | C17—H17a | 0.99 |
C7—C8 | 1.508 (3) | C17—H17b | 0.99 |
C6—C25 | 1.517 (3) | C18—H18 | 0.95 |
C7—C15 | 1.549 (3) | C19—H19 | 0.95 |
C7—C21 | 1.537 (3) | C21—H21 | 1 |
C8—C9 | 1.410 (3) | C23—H23a | 0.98 |
C8—C14 | 1.382 (3) | C23—H23b | 0.98 |
C9—C10 | 1.370 (3) | C23—H23c | 0.98 |
C10—C12 | 1.377 (4) | C24—H24a | 0.99 |
C12—C13 | 1.362 (3) | C24—H24b | 0.99 |
C13—C14 | 1.388 (4) | C25—H25a | 0.99 |
C15—C16 | 1.537 (3) | C25—H25b | 0.99 |
C17—C18 | 1.476 (4) | ||
C1—O1—C2 | 114.2 (2) | C6—C25—C24 | 110.1 (2) |
C4—O3—C5 | 116.3 (2) | C3—O9—H1o | 108 (3) |
C22—O5—C23 | 115.8 (2) | O1—C1—H1a | 109.5 |
C10—O7—C11 | 104.8 (2) | O1—C1—H1b | 109.5 |
C11—O8—C12 | 105.6 (2) | H1a—C1—H1b | 109.5 |
C2—N1—C3 | 116.0 (2) | O1—C1—H1C | 109.5 |
C2—N1—C9 | 124.2 (2) | H1a—C1—H1C | 109.5 |
C3—N1—C9 | 119.3 (2) | H1b—C1—H1C | 109.5 |
C16—N2—C17 | 121.3 (2) | O3—C5—H5a | 109.5 |
C16—N2—C21 | 110.1 (2) | O3—C5—H5b | 109.5 |
C17—N2—C21 | 117.4 (2) | H5a—C5—H5b | 109.5 |
O1—C2—O2 | 125.2 (2) | O3—C5—H5C | 109.5 |
O1—C2—N1 | 112.3 (2) | H5a—C5—H5C | 109.5 |
O2—C2—N1 | 122.4 (2) | H5b—C5—H5C | 109.5 |
O9—C3—N1 | 111.8 (2) | C25—C6—H6 | 103.8 |
O9—C3—C4 | 109.8 (2) | C7—C6—H6 | 103.8 |
O9—C3—C6 | 105.5 (2) | C3—C6—H6 | 103.8 |
N1—C3—C4 | 110.1 (2) | O8—C11—H11a | 109.9 |
N1—C3—C6 | 109.4 (2) | O7—C11—H11a | 109.9 |
C4—C3—C6 | 110.2 (2) | O8—C11—H11b | 109.9 |
O3—C4—O4 | 123.9 (3) | O7—C11—H11b | 109.9 |
O3—C4—C3 | 111.8 (2) | H11a—C11—H11b | 108.3 |
O4—C4—C3 | 124.1 (3) | C12—C13—H13 | 122.0 |
C3—C6—C25 | 113.6 (2) | C14—C13—H13 | 122.0 |
C7—C6—C25 | 115.2 (2) | C8—C14—H14 | 118.8 |
C3—C6—C7 | 114.7 (2) | C13—C14—H14 | 118.8 |
C6—C7—C8 | 103.7 (2) | C16—C15—H15a | 111.3 |
C6—C7—C21 | 109.1 (2) | C7—C15—H15a | 111.3 |
C8—C7—C15 | 108.6 (2) | C16—C15—H15b | 111.3 |
C8—C7—C21 | 111.7 (2) | C7—C15—H15b | 111.3 |
C6—C7—C15 | 123.2 (2) | H15a—C15—H15b | 109.2 |
C15—C7—C21 | 100.6 (2) | N2—C16—H16a | 110.6 |
C7—C8—C9 | 116.2 (2) | C15—C16—H16a | 110.6 |
C7—C8—C14 | 123.8 (2) | N2—C16—H16b | 110.6 |
C9—C8—C14 | 119.9 (2) | C15—C16—H16b | 110.6 |
C8—C9—C10 | 117.4 (2) | H16a—C16—H16b | 108.7 |
C8—C9—N1 | 118.6 (2) | N2—C17—H17a | 109.0 |
C10—C9—N1 | 123.9 (2) | C18—C17—H17a | 109.0 |
O7—C10—C9 | 128.5 (2) | N2—C17—H17b | 109.0 |
O7—C10—C12 | 110.7 (2) | C18—C17—H17b | 109.0 |
C9—C10—C12 | 120.8 (2) | H17a—C17—H17b | 107.8 |
O7—C11—O8 | 108.9 (2) | C19—C18—H18 | 118.0 |
C13—C12—O8 | 126.9 (2) | C17—C18—H18 | 118.0 |
C10—C12—C13 | 123.4 (2) | C18—C19—H19 | 120.3 |
O8—C12—C10 | 109.7 (2) | C20—C19—H19 | 120.3 |
C12—C13—C14 | 116.0 (2) | N2—C21—H21 | 107.0 |
C8—C14—C13 | 122.4 (2) | C7—C21—H21 | 107.0 |
C7—C15—C16 | 102.4 (2) | C20—C21—H21 | 107.0 |
N2—C16—C15 | 105.7 (2) | O5—C23—H23a | 109.5 |
N2—C17—C18 | 113.0 (2) | O5—C23—H23b | 109.5 |
C17—C18—C19 | 124.1 (2) | H23a—C23—H23b | 109.5 |
C18—C19—C20 | 119.5 (3) | O5—C23—H23C | 109.5 |
C19—C20—C22 | 102.2 (2) | H23a—C23—H23C | 109.5 |
C19—C20—C24 | 116.7 (2) | H23b—C23—H23C | 109.5 |
C19—C20—C21 | 103.3 (2) | C20—C24—H24a | 109.9 |
C21—C20—C22 | 117.0 (2) | C25—C24—H24a | 109.9 |
C21—C20—C24 | 107.8 (2) | C20—C24—H24b | 109.9 |
C22—C20—C24 | 110.1 (2) | C25—C24—H24b | 109.9 |
N2—C21—C7 | 104.1 (2) | H24a—C24—H24b | 108.3 |
N2—C21—C20 | 113.6 (2) | C6—C25—H25a | 109.6 |
C7—C21—C20 | 117.7 (2) | C24—C25—H25a | 109.6 |
O5—C22—O6 | 121.9 (2) | C6—C25—H25b | 109.6 |
O5—C22—C20 | 110.7 (2) | C24—C25—H25b | 109.6 |
O6—C22—C20 | 127.2 (2) | H25a—C25—H25b | 108.2 |
C20—C24—C25 | 109.1 (2) | ||
C1—O1—C2—O2 | −0.8 (3) | C11—O8—C12—C13 | 175.6 (3) |
C1—O1—C2—N1 | −177.7 (2) | C11—O8—C12—C10 | −4.4 (3) |
C9—N1—C2—O2 | 159.0 (2) | O7—C10—C12—C13 | −177.6 (2) |
C3—N1—C2—O2 | −12.9 (3) | C9—C10—C12—C13 | 2.3 (4) |
C9—N1—C2—O1 | −24.1 (3) | O7—C10—C12—O8 | 2.5 (3) |
C3—N1—C2—O1 | 164.1 (2) | C9—C10—C12—O8 | −177.7 (2) |
C2—N1—C3—O9 | 81.2 (3) | O8—C12—C13—C14 | 178.9 (2) |
C9—N1—C3—O9 | −91.1 (2) | C10—C12—C13—C14 | −1.0 (4) |
C2—N1—C3—C4 | −41.1 (3) | C9—C8—C14—C13 | −0.9 (4) |
C9—N1—C3—C4 | 146.6 (2) | C7—C8—C14—C13 | 176.5 (2) |
C2—N1—C3—C6 | −162.3 (2) | C12—C13—C14—C8 | 0.4 (4) |
C9—N1—C3—C6 | 25.4 (3) | C8—C7—C15—C16 | −79.5 (2) |
C5—O3—C4—O4 | 1.6 (4) | C21—C7—C15—C16 | 37.9 (2) |
C5—O3—C4—C3 | −174.0 (2) | C6—C7—C15—C16 | 159.3 (2) |
O9—C3—C4—O4 | 16.5 (4) | C21—N2—C16—C15 | −1.9 (3) |
N1—C3—C4—O4 | 140.0 (3) | C17—N2—C16—C15 | −144.6 (2) |
C6—C3—C4—O4 | −99.3 (3) | C7—C15—C16—N2 | −23.3 (2) |
O9—C3—C4—O3 | −168.0 (2) | C21—N2—C17—C18 | 0.6 (3) |
N1—C3—C4—O3 | −44.5 (3) | C16—N2—C17—C18 | 140.8 (2) |
C6—C3—C4—O3 | 76.3 (3) | N2—C17—C18—C19 | −23.1 (4) |
O9—C3—C6—C25 | −76.8 (2) | C17—C18—C19—C20 | −0.5 (4) |
N1—C3—C6—C25 | 162.8 (2) | C18—C19—C20—C24 | 158.1 (2) |
C4—C3—C6—C25 | 41.6 (3) | C18—C19—C20—C22 | −81.8 (3) |
O9—C3—C6—C7 | 147.7 (2) | C18—C19—C20—C21 | 40.0 (3) |
N1—C3—C6—C7 | 27.3 (3) | C16—N2—C21—C7 | 26.7 (2) |
C4—C3—C6—C7 | −93.9 (3) | C17—N2—C21—C7 | 171.1 (2) |
C25—C6—C7—C8 | 163.3 (2) | C16—N2—C21—C20 | −102.5 (2) |
C3—C6—C7—C8 | −61.9 (2) | C17—N2—C21—C20 | 41.9 (3) |
C25—C6—C7—C21 | 44.1 (3) | C8—C7—C21—N2 | 75.2 (2) |
C3—C6—C7—C21 | 178.9 (2) | C6—C7—C21—N2 | −170.7 (2) |
C25—C6—C7—C15 | −73.2 (3) | C15—C7—C21—N2 | −39.9 (2) |
C3—C6—C7—C15 | 61.6 (3) | C8—C7—C21—C20 | −158.2 (2) |
C21—C7—C8—C14 | −13.1 (3) | C6—C7—C21—C20 | −44.1 (2) |
C6—C7—C8—C14 | −130.6 (2) | C15—C7—C21—C20 | 86.7 (2) |
C15—C7—C8—C14 | 96.9 (3) | C19—C20—C21—N2 | −60.2 (2) |
C21—C7—C8—C9 | 164.3 (2) | C24—C20—C21—N2 | 175.7 (2) |
C6—C7—C8—C9 | 46.9 (2) | C22—C20—C21—N2 | 51.1 (3) |
C15—C7—C8—C9 | −85.6 (2) | C19—C20—C21—C7 | 177.9 (2) |
C14—C8—C9—C10 | 2.0 (3) | C24—C20—C21—C7 | 53.8 (3) |
C7—C8—C9—C10 | −175.6 (2) | C22—C20—C21—C7 | −70.7 (3) |
C14—C8—C9—N1 | 178.3 (2) | C23—O5—C22—O6 | −0.1 (3) |
C7—C8—C9—N1 | 0.7 (3) | C23—O5—C22—C20 | 174.3 (2) |
C2—N1—C9—C10 | −37.8 (3) | C19—C20—C22—O6 | 87.4 (3) |
C3—N1—C9—C10 | 133.8 (2) | C24—C20—C22—O6 | −148.0 (2) |
C2—N1—C9—C8 | 146.2 (2) | C21—C20—C22—O6 | −24.6 (3) |
C3—N1—C9—C8 | −42.2 (3) | C19—C20—C22—O5 | −86.6 (2) |
C11—O7—C10—C9 | −179.2 (3) | C24—C20—C22—O5 | 38.0 (3) |
C11—O7—C10—C12 | 0.6 (3) | C21—C20—C22—O5 | 161.4 (2) |
C8—C9—C10—O7 | 177.2 (2) | C19—C20—C24—C25 | −176.6 (2) |
N1—C9—C10—O7 | 1.1 (4) | C22—C20—C24—C25 | 67.6 (3) |
C8—C9—C10—C12 | −2.6 (3) | C21—C20—C24—C25 | −61.0 (2) |
N1—C9—C10—C12 | −178.7 (2) | C7—C6—C25—C24 | −55.6 (3) |
C12—O8—C11—O7 | 4.8 (3) | C3—C6—C25—C24 | 169.1 (2) |
C10—O7—C11—O8 | −3.4 (3) | C20—C24—C25—C6 | 63.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H1o···O6i | 0.80 (4) | 2.26 (4) | 2.873 (2) | 133 (3) |
Symmetry code: (i) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C25H28N2O9 |
Mr | 500.49 |
Crystal system, space group | Monoclinic, C2 |
Temperature (K) | 168 |
a, b, c (Å) | 29.005 (2), 8.5430 (6), 9.3081 (7) |
β (°) | 96.163 (1) |
V (Å3) | 2293.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.50 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker AXS CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15060, 2493, 2173 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.084, 1.02 |
No. of reflections | 2493 |
No. of parameters | 329 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.18 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
O1—C1 | 1.449 (3) | C3—C6 | 1.549 (3) |
O1—C2 | 1.317 (3) | C6—C7 | 1.548 (3) |
O2—C2 | 1.206 (3) | C7—C8 | 1.508 (3) |
O3—C4 | 1.337 (4) | C6—C25 | 1.517 (3) |
O3—C5 | 1.447 (3) | C7—C15 | 1.549 (3) |
O4—C4 | 1.182 (3) | C7—C21 | 1.537 (3) |
O5—C22 | 1.325 (4) | C8—C9 | 1.410 (3) |
O5—C23 | 1.448 (3) | C8—C14 | 1.382 (3) |
O6—C22 | 1.202 (3) | C9—C10 | 1.370 (3) |
O7—C10 | 1.370 (3) | C10—C12 | 1.377 (4) |
O7—C11 | 1.432 (3) | C12—C13 | 1.362 (3) |
O8—C11 | 1.425 (3) | C13—C14 | 1.388 (4) |
O8—C12 | 1.369 (3) | C15—C16 | 1.537 (3) |
O9—C3 | 1.396 (3) | C17—C18 | 1.476 (4) |
N1—C2 | 1.381 (3) | C18—C19 | 1.319 (4) |
N1—C3 | 1.453 (3) | C19—C20 | 1.520 (3) |
N1—C9 | 1.423 (3) | C20—C21 | 1.545 (3) |
N2—C16 | 1.459 (3) | C20—C22 | 1.536 (3) |
N2—C17 | 1.467 (3) | C20—C24 | 1.523 (4) |
N2—C21 | 1.433 (3) | C24—C25 | 1.526 (4) |
C3—C4 | 1.541 (4) | ||
C1—O1—C2 | 114.2 (2) | C7—C8—C14 | 123.8 (2) |
C4—O3—C5 | 116.3 (2) | C9—C8—C14 | 119.9 (2) |
C22—O5—C23 | 115.8 (2) | C8—C9—C10 | 117.4 (2) |
C10—O7—C11 | 104.8 (2) | C8—C9—N1 | 118.6 (2) |
C11—O8—C12 | 105.6 (2) | C10—C9—N1 | 123.9 (2) |
C2—N1—C3 | 116.0 (2) | O7—C10—C9 | 128.5 (2) |
C2—N1—C9 | 124.2 (2) | O7—C10—C12 | 110.7 (2) |
C3—N1—C9 | 119.3 (2) | C9—C10—C12 | 120.8 (2) |
C16—N2—C17 | 121.3 (2) | O7—C11—O8 | 108.9 (2) |
C16—N2—C21 | 110.1 (2) | C13—C12—O8 | 126.9 (2) |
C17—N2—C21 | 117.4 (2) | C10—C12—C13 | 123.4 (2) |
O1—C2—O2 | 125.2 (2) | O8—C12—C10 | 109.7 (2) |
O1—C2—N1 | 112.3 (2) | C12—C13—C14 | 116.0 (2) |
O2—C2—N1 | 122.4 (2) | C8—C14—C13 | 122.4 (2) |
O9—C3—N1 | 111.8 (2) | C7—C15—C16 | 102.4 (2) |
O9—C3—C4 | 109.8 (2) | N2—C16—C15 | 105.7 (2) |
O9—C3—C6 | 105.5 (2) | N2—C17—C18 | 113.0 (2) |
N1—C3—C4 | 110.1 (2) | C17—C18—C19 | 124.1 (2) |
N1—C3—C6 | 109.4 (2) | C18—C19—C20 | 119.5 (3) |
C4—C3—C6 | 110.2 (2) | C19—C20—C22 | 102.2 (2) |
O3—C4—O4 | 123.9 (3) | C19—C20—C24 | 116.7 (2) |
O3—C4—C3 | 111.8 (2) | C19—C20—C21 | 103.3 (2) |
O4—C4—C3 | 124.1 (3) | C21—C20—C22 | 117.0 (2) |
C3—C6—C25 | 113.6 (2) | C21—C20—C24 | 107.8 (2) |
C7—C6—C25 | 115.2 (2) | C22—C20—C24 | 110.1 (2) |
C3—C6—C7 | 114.7 (2) | N2—C21—C7 | 104.1 (2) |
C6—C7—C8 | 103.7 (2) | N2—C21—C20 | 113.6 (2) |
C6—C7—C21 | 109.1 (2) | C7—C21—C20 | 117.7 (2) |
C8—C7—C15 | 108.6 (2) | O5—C22—O6 | 121.9 (2) |
C8—C7—C21 | 111.7 (2) | O5—C22—C20 | 110.7 (2) |
C6—C7—C15 | 123.2 (2) | O6—C22—C20 | 127.2 (2) |
C15—C7—C21 | 100.6 (2) | C20—C24—C25 | 109.1 (2) |
C7—C8—C9 | 116.2 (2) | C6—C25—C24 | 110.1 (2) |
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Mersinines A and B, and mersiloscine are pentacyclic quinolinic alkaloids that are found within the genus Kopsia. These alkaloids contain a meloscine skeleton whose five-membered C ring has an additional C atom. The title alkaloid, mersinine A, (I), isolated from the leaves of Kopsia fruticosa (Ker.) A. DC., possesses a tetrahydroquinoline chromophore and its structure has been determined by solution NMR spectroscopy (Kam et al., 2001). The present study reports the solid-state structure, which confirms the NMR results (Fig. 1). The hydroxyl group forms a hydrogen bond to the carbonyl O atom of an adjacent carboxyl unit [O9···O6i 2.873 (2) Å and O9—H9o···O6i 133 (3)°; symmetry code: (i) x, y, z − 1], thus giving rise to linear chains running along the c axis of the crystal.