Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006414/bt6134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006414/bt6134Isup2.hkl |
CCDC reference: 185784
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.178
- Data-to-parameter ratio = 14.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Compound (I) was obtained by reduction of 1-oxo-13c-methoxy-1,13c-dihydrodibenzo[a,kl]xanthene, (II), in ethyl acetate in the presence of hydrogen under Pd/C catalysis. (I) was the main product in a yield of 90%. A single-crystal suitable for X-ray analysis was recrystallized from methanol (m.p. 427–428 K). νmax: 1727, 1581, 1456, 1267, 1066. δH (300 MHz in acetone/TMS): 2.61 (dt, J = 9.0 Hz, 17.7 Hz, 1H, –CH2), 2.80 (s, 3H, OCH3), 3.06 (dd, J = 8.4 Hz, 15.6 Hz 1H, –CH2), 3.29 (dd, J = 9.0 Hz, 17.7 Hz, 1H, –CH2), 3.88 (dt, J = 8.7 Hz, 15.9 Hz, 1H, –CH2), 7.13–7.17 (m, 2H, H4, H6), 7.35 (d, J = 9.0 Hz, 1H, H9), 7.42–7.47 (m, 3H, H5, H10, H13), 7.88–7.91 (m, 1H, H11), 7.98 (d, J = 9.0 Hz, 1H, H8), 8.09–8.12 (m, 1H, H12). δC (300 MHz): 28.36 (CH2), 30.52 (CH2), 50.60 (OCH3), 79.14 (13c-C), 109.28, 114.82, 116.95, 118.02, 123.86, 125.23, 126.85, 128.12, 129.20, 131.64, 131.92, 132.47, 133.29, 141.57, 152.09, 152.50, 203.08 (C═O). FAB–MS m/z (%): 317 (M+ + 1, 22), 316 (M+, 18), 285 (M+ –OCH3, 58).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids. | |
Fig. 2. The packing arrangement of (I) viewed along the a axis. |
C21H16O3 | Dx = 1.354 Mg m−3 |
Mr = 316.34 | Melting point: 427-428K K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.736 (4) Å | Cell parameters from 843 reflections |
b = 11.104 (6) Å | θ = 3.9–24.9° |
c = 18.183 (9) Å | µ = 0.09 mm−1 |
β = 96.570 (11)° | T = 293 K |
V = 1551.6 (14) Å3 | Column, colorless |
Z = 4 | 0.45 × 0.30 × 0.15 mm |
F(000) = 664 |
Bruker SMART1000 CCD diffractometer | 3166 independent reflections |
Radiation source: fine-focus sealed tube | 1817 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ϕ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | h = −8→9 |
Tmin = 0.961, Tmax = 0.987 | k = −11→13 |
8639 measured reflections | l = −22→19 |
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)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.178 | w = 1/[σ2(Fo2) + (0.1064P)2 + 0.0469P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3166 reflections | Δρmax = 0.19 e Å−3 |
218 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (3) |
C21H16O3 | V = 1551.6 (14) Å3 |
Mr = 316.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.736 (4) Å | µ = 0.09 mm−1 |
b = 11.104 (6) Å | T = 293 K |
c = 18.183 (9) Å | 0.45 × 0.30 × 0.15 mm |
β = 96.570 (11)° |
Bruker SMART1000 CCD diffractometer | 3166 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | 1817 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.987 | Rint = 0.032 |
8639 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.19 e Å−3 |
3166 reflections | Δρmin = −0.18 e Å−3 |
218 parameters |
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 | 0.51108 (19) | 0.89425 (14) | 0.24474 (8) | 0.0534 (4) | |
O2 | 0.02682 (18) | 0.84231 (13) | 0.29130 (8) | 0.0463 (4) | |
O3 | 0.1503 (2) | 1.11628 (15) | 0.35660 (9) | 0.0628 (5) | |
C1 | 0.3752 (3) | 0.9294 (2) | 0.19416 (12) | 0.0485 (6) | |
C2 | 0.4122 (4) | 0.9473 (2) | 0.12249 (14) | 0.0628 (7) | |
H2A | 0.5213 | 0.9281 | 0.1089 | 0.075* | |
C3 | 0.2847 (4) | 0.9942 (3) | 0.07145 (14) | 0.0738 (8) | |
H3A | 0.3092 | 1.0084 | 0.0233 | 0.089* | |
C4 | 0.1214 (4) | 1.0204 (2) | 0.09044 (14) | 0.0666 (7) | |
H4A | 0.0379 | 1.0538 | 0.0555 | 0.080* | |
C5 | 0.0814 (3) | 0.9972 (2) | 0.16133 (12) | 0.0513 (6) | |
C6 | 0.2114 (3) | 0.94939 (18) | 0.21410 (11) | 0.0436 (5) | |
C7 | 0.1668 (3) | 0.92797 (18) | 0.29168 (11) | 0.0418 (5) | |
C8 | 0.0826 (3) | 1.04767 (19) | 0.31029 (13) | 0.0470 (6) | |
C9 | −0.0833 (3) | 1.0780 (2) | 0.26218 (13) | 0.0553 (6) | |
H9A | −0.0925 | 1.1648 | 0.2574 | 0.066* | |
H9B | −0.1813 | 1.0502 | 0.2865 | 0.066* | |
C10 | −0.0951 (3) | 1.0222 (2) | 0.18475 (14) | 0.0602 (7) | |
H10A | −0.1604 | 0.9476 | 0.1843 | 0.072* | |
H10B | −0.1577 | 1.0767 | 0.1495 | 0.072* | |
C11 | 0.0695 (3) | 0.7243 (2) | 0.27040 (14) | 0.0585 (7) | |
H11A | −0.0299 | 0.6728 | 0.2717 | 0.088* | |
H11B | 0.1642 | 0.6944 | 0.3041 | 0.088* | |
H11C | 0.1029 | 0.7255 | 0.2212 | 0.088* | |
C12 | 0.4830 (3) | 0.87999 (19) | 0.31825 (12) | 0.0456 (5) | |
C13 | 0.3243 (3) | 0.89315 (18) | 0.34337 (11) | 0.0423 (5) | |
C14 | 0.3144 (3) | 0.86835 (19) | 0.42057 (12) | 0.0461 (6) | |
C15 | 0.1566 (3) | 0.8709 (2) | 0.45268 (13) | 0.0555 (6) | |
H15A | 0.0545 | 0.8930 | 0.4238 | 0.067* | |
C16 | 0.1507 (4) | 0.8417 (3) | 0.52522 (14) | 0.0675 (7) | |
H16A | 0.0448 | 0.8432 | 0.5448 | 0.081* | |
C17 | 0.3016 (4) | 0.8095 (3) | 0.57033 (14) | 0.0732 (8) | |
H17A | 0.2958 | 0.7885 | 0.6195 | 0.088* | |
C18 | 0.4574 (4) | 0.8088 (2) | 0.54223 (13) | 0.0669 (7) | |
H18A | 0.5584 | 0.7900 | 0.5729 | 0.080* | |
C19 | 0.4669 (3) | 0.8364 (2) | 0.46712 (12) | 0.0525 (6) | |
C20 | 0.6268 (3) | 0.8297 (2) | 0.43747 (14) | 0.0592 (7) | |
H20A | 0.7277 | 0.8115 | 0.4683 | 0.071* | |
C21 | 0.6353 (3) | 0.8497 (2) | 0.36420 (14) | 0.0544 (6) | |
H21A | 0.7409 | 0.8433 | 0.3447 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0425 (9) | 0.0641 (10) | 0.0552 (10) | 0.0017 (7) | 0.0122 (7) | 0.0012 (8) |
O2 | 0.0355 (8) | 0.0410 (8) | 0.0625 (10) | −0.0030 (6) | 0.0060 (7) | 0.0002 (7) |
O3 | 0.0617 (11) | 0.0549 (10) | 0.0720 (11) | −0.0019 (8) | 0.0088 (9) | −0.0165 (8) |
C1 | 0.0460 (13) | 0.0479 (13) | 0.0521 (13) | −0.0032 (10) | 0.0081 (11) | −0.0044 (10) |
C2 | 0.0648 (17) | 0.0718 (17) | 0.0538 (15) | −0.0064 (13) | 0.0159 (13) | −0.0040 (12) |
C3 | 0.086 (2) | 0.089 (2) | 0.0483 (15) | −0.0110 (17) | 0.0125 (15) | −0.0017 (14) |
C4 | 0.0745 (19) | 0.0727 (18) | 0.0503 (15) | −0.0052 (14) | −0.0021 (13) | 0.0044 (12) |
C5 | 0.0533 (14) | 0.0467 (13) | 0.0524 (14) | −0.0041 (11) | 0.0001 (11) | 0.0000 (10) |
C6 | 0.0463 (13) | 0.0394 (11) | 0.0451 (12) | −0.0041 (9) | 0.0052 (10) | −0.0029 (9) |
C7 | 0.0379 (11) | 0.0388 (12) | 0.0491 (12) | −0.0037 (9) | 0.0066 (9) | −0.0021 (9) |
C8 | 0.0426 (12) | 0.0428 (13) | 0.0573 (14) | −0.0036 (10) | 0.0126 (10) | −0.0007 (10) |
C9 | 0.0485 (14) | 0.0471 (13) | 0.0701 (16) | 0.0069 (10) | 0.0061 (11) | 0.0054 (11) |
C10 | 0.0501 (15) | 0.0546 (15) | 0.0730 (17) | 0.0007 (11) | −0.0053 (12) | 0.0047 (12) |
C11 | 0.0565 (15) | 0.0411 (13) | 0.0767 (17) | −0.0043 (11) | 0.0023 (12) | −0.0060 (12) |
C12 | 0.0434 (13) | 0.0439 (12) | 0.0498 (13) | −0.0013 (10) | 0.0065 (10) | −0.0011 (10) |
C13 | 0.0367 (11) | 0.0421 (12) | 0.0485 (12) | −0.0003 (9) | 0.0063 (9) | −0.0031 (9) |
C14 | 0.0435 (13) | 0.0462 (13) | 0.0482 (13) | −0.0024 (10) | 0.0034 (10) | −0.0050 (10) |
C15 | 0.0522 (14) | 0.0652 (16) | 0.0494 (14) | 0.0017 (11) | 0.0070 (11) | −0.0020 (11) |
C16 | 0.0667 (17) | 0.084 (2) | 0.0541 (15) | −0.0009 (14) | 0.0160 (13) | −0.0021 (13) |
C17 | 0.085 (2) | 0.087 (2) | 0.0476 (15) | −0.0007 (16) | 0.0074 (14) | −0.0016 (13) |
C18 | 0.0710 (19) | 0.0742 (18) | 0.0522 (16) | 0.0011 (14) | −0.0081 (13) | −0.0025 (13) |
C19 | 0.0508 (14) | 0.0537 (14) | 0.0514 (14) | −0.0009 (11) | −0.0015 (11) | −0.0045 (10) |
C20 | 0.0440 (13) | 0.0633 (16) | 0.0675 (17) | −0.0005 (11) | −0.0059 (12) | −0.0020 (12) |
C21 | 0.0380 (13) | 0.0563 (15) | 0.0687 (17) | 0.0006 (10) | 0.0053 (11) | −0.0026 (12) |
O1—C1 | 1.372 (3) | C10—H10A | 0.9700 |
O1—C12 | 1.388 (3) | C10—H10B | 0.9700 |
O2—C11 | 1.414 (3) | C11—H11A | 0.9600 |
O2—C7 | 1.441 (2) | C11—H11B | 0.9600 |
O3—C8 | 1.209 (3) | C11—H11C | 0.9600 |
C1—C6 | 1.375 (3) | C12—C13 | 1.366 (3) |
C1—C2 | 1.380 (3) | C12—C21 | 1.405 (3) |
C2—C3 | 1.377 (4) | C13—C14 | 1.441 (3) |
C2—H2A | 0.9300 | C14—C15 | 1.413 (3) |
C3—C4 | 1.378 (4) | C14—C19 | 1.416 (3) |
C3—H3A | 0.9300 | C15—C16 | 1.364 (3) |
C4—C5 | 1.384 (3) | C15—H15A | 0.9300 |
C4—H4A | 0.9300 | C16—C17 | 1.394 (4) |
C5—C6 | 1.412 (3) | C16—H16A | 0.9300 |
C5—C10 | 1.502 (3) | C17—C18 | 1.362 (4) |
C6—C7 | 1.509 (3) | C17—H17A | 0.9300 |
C7—C13 | 1.502 (3) | C18—C19 | 1.410 (3) |
C7—C8 | 1.535 (3) | C18—H18A | 0.9300 |
C8—C9 | 1.506 (3) | C19—C20 | 1.406 (3) |
C9—C10 | 1.531 (3) | C20—C21 | 1.360 (3) |
C9—H9A | 0.9700 | C20—H20A | 0.9300 |
C9—H9B | 0.9700 | C21—H21A | 0.9300 |
C1—O1—C12 | 119.08 (17) | C9—C10—H10B | 109.2 |
C11—O2—C7 | 114.51 (16) | H10A—C10—H10B | 107.9 |
O1—C1—C6 | 121.8 (2) | O2—C11—H11A | 109.5 |
O1—C1—C2 | 116.6 (2) | O2—C11—H11B | 109.5 |
C6—C1—C2 | 121.5 (2) | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 118.7 (3) | O2—C11—H11C | 109.5 |
C3—C2—H2A | 120.6 | H11A—C11—H11C | 109.5 |
C1—C2—H2A | 120.6 | H11B—C11—H11C | 109.5 |
C2—C3—C4 | 121.2 (2) | C13—C12—O1 | 123.75 (19) |
C2—C3—H3A | 119.4 | C13—C12—C21 | 123.5 (2) |
C4—C3—H3A | 119.4 | O1—C12—C21 | 112.78 (19) |
C3—C4—C5 | 120.2 (3) | C12—C13—C14 | 117.06 (19) |
C3—C4—H4A | 119.9 | C12—C13—C7 | 120.95 (19) |
C5—C4—H4A | 119.9 | C14—C13—C7 | 121.96 (18) |
C4—C5—C6 | 119.0 (2) | C15—C14—C19 | 117.3 (2) |
C4—C5—C10 | 122.5 (2) | C15—C14—C13 | 122.9 (2) |
C6—C5—C10 | 118.5 (2) | C19—C14—C13 | 119.8 (2) |
C1—C6—C5 | 119.2 (2) | C16—C15—C14 | 121.4 (2) |
C1—C6—C7 | 122.51 (19) | C16—C15—H15A | 119.3 |
C5—C6—C7 | 118.2 (2) | C14—C15—H15A | 119.3 |
O2—C7—C13 | 112.86 (16) | C15—C16—C17 | 120.8 (3) |
O2—C7—C6 | 110.61 (16) | C15—C16—H16A | 119.6 |
C13—C7—C6 | 111.69 (18) | C17—C16—H16A | 119.6 |
O2—C7—C8 | 103.61 (16) | C18—C17—C16 | 119.9 (2) |
C13—C7—C8 | 114.79 (17) | C18—C17—H17A | 120.1 |
C6—C7—C8 | 102.58 (16) | C16—C17—H17A | 120.1 |
O3—C8—C9 | 122.4 (2) | C17—C18—C19 | 120.6 (2) |
O3—C8—C7 | 122.6 (2) | C17—C18—H18A | 119.7 |
C9—C8—C7 | 114.85 (18) | C19—C18—H18A | 119.7 |
C8—C9—C10 | 113.63 (19) | C20—C19—C18 | 120.4 (2) |
C8—C9—H9A | 108.8 | C20—C19—C14 | 119.5 (2) |
C10—C9—H9A | 108.8 | C18—C19—C14 | 120.1 (2) |
C8—C9—H9B | 108.8 | C21—C20—C19 | 120.7 (2) |
C10—C9—H9B | 108.8 | C21—C20—H20A | 119.7 |
H9A—C9—H9B | 107.7 | C19—C20—H20A | 119.7 |
C5—C10—C9 | 112.0 (2) | C20—C21—C12 | 119.4 (2) |
C5—C10—H10A | 109.2 | C20—C21—H21A | 120.3 |
C9—C10—H10A | 109.2 | C12—C21—H21A | 120.3 |
C5—C10—H10B | 109.2 | ||
C12—O1—C1—C6 | −0.9 (3) | C6—C5—C10—C9 | 41.0 (3) |
C12—O1—C1—C2 | 177.24 (19) | C8—C9—C10—C5 | −25.1 (3) |
O1—C1—C2—C3 | −173.6 (2) | C1—O1—C12—C13 | 3.4 (3) |
C6—C1—C2—C3 | 4.5 (4) | C1—O1—C12—C21 | −177.01 (19) |
C1—C2—C3—C4 | −1.5 (4) | O1—C12—C13—C14 | 176.40 (18) |
C2—C3—C4—C5 | −1.5 (4) | C21—C12—C13—C14 | −3.1 (3) |
C3—C4—C5—C6 | 1.6 (4) | O1—C12—C13—C7 | −1.6 (3) |
C3—C4—C5—C10 | −179.1 (2) | C21—C12—C13—C7 | 178.86 (19) |
O1—C1—C6—C5 | 173.61 (19) | O2—C7—C13—C12 | 123.1 (2) |
C2—C1—C6—C5 | −4.4 (3) | C6—C7—C13—C12 | −2.2 (3) |
O1—C1—C6—C7 | −3.3 (3) | C8—C7—C13—C12 | −118.5 (2) |
C2—C1—C6—C7 | 178.67 (19) | O2—C7—C13—C14 | −54.8 (3) |
C4—C5—C6—C1 | 1.3 (3) | C6—C7—C13—C14 | 179.84 (18) |
C10—C5—C6—C1 | −178.01 (19) | C8—C7—C13—C14 | 63.6 (3) |
C4—C5—C6—C7 | 178.3 (2) | C12—C13—C14—C15 | −175.8 (2) |
C10—C5—C6—C7 | −1.0 (3) | C7—C13—C14—C15 | 2.2 (3) |
C11—O2—C7—C13 | −59.2 (2) | C12—C13—C14—C19 | 2.3 (3) |
C11—O2—C7—C6 | 66.7 (2) | C7—C13—C14—C19 | −179.69 (19) |
C11—O2—C7—C8 | 176.02 (17) | C19—C14—C15—C16 | −1.2 (3) |
C1—C6—C7—O2 | −122.0 (2) | C13—C14—C15—C16 | 177.0 (2) |
C5—C6—C7—O2 | 61.1 (2) | C14—C15—C16—C17 | 0.7 (4) |
C1—C6—C7—C13 | 4.6 (3) | C15—C16—C17—C18 | 1.0 (4) |
C5—C6—C7—C13 | −172.28 (18) | C16—C17—C18—C19 | −2.2 (4) |
C1—C6—C7—C8 | 128.1 (2) | C17—C18—C19—C20 | −176.8 (2) |
C5—C6—C7—C8 | −48.8 (2) | C17—C18—C19—C14 | 1.7 (4) |
O2—C7—C8—O3 | 132.9 (2) | C15—C14—C19—C20 | 178.5 (2) |
C13—C7—C8—O3 | 9.4 (3) | C13—C14—C19—C20 | 0.2 (3) |
C6—C7—C8—O3 | −111.9 (2) | C15—C14—C19—C18 | 0.0 (3) |
O2—C7—C8—C9 | −51.9 (2) | C13—C14—C19—C18 | −178.2 (2) |
C13—C7—C8—C9 | −175.41 (18) | C18—C19—C20—C21 | 176.3 (2) |
C6—C7—C8—C9 | 63.2 (2) | C14—C19—C20—C21 | −2.2 (4) |
O3—C8—C9—C10 | 147.9 (2) | C19—C20—C21—C12 | 1.5 (4) |
C7—C8—C9—C10 | −27.2 (3) | C13—C12—C21—C20 | 1.3 (3) |
C4—C5—C10—C9 | −138.3 (2) | O1—C12—C21—C20 | −178.3 (2) |
Experimental details
Crystal data | |
Chemical formula | C21H16O3 |
Mr | 316.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.736 (4), 11.104 (6), 18.183 (9) |
β (°) | 96.570 (11) |
V (Å3) | 1551.6 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.45 × 0.30 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART1000 CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) |
Tmin, Tmax | 0.961, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8639, 3166, 1817 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.178, 1.01 |
No. of reflections | 3166 |
No. of parameters | 218 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.18 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
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Chiral amines are useful resolving agents, chiral building blocks and chiral auxiliaries in important stereoselective organic synthesis, such as asymmetric reduction, asymmetric epoxidation, asymmetric addition, asymmetric condensation, and resolution of racemic compounds. (Aldous et al., 2000; Kawamoto & Wills, 2000; Hashihayata et al., 1997; Dai et al., 2000; Enders & Ullrich, 2000). The title compound, (I), is a key intermediate for chiral amines that we are designing for potential use as chiral additives and auxiliaries in asymmetric synthesis. Information on the crystal structure (I) is useful for studying the stereoselection of its reductive amination reaction. Compound (I) was obtained by reduction of 1-oxo-13c-propoxy-1,13c-dihydrodibenzo[a,kl]xanthene(Tan et al., 2001) with hydrogen under Pd/C catalysis. The reduction reaction takes place at room temperature in high yield. The structure of (I) was also confirmed by 1H NMR, 13C NMR, IR and FAB-MS spectroscopic analysis. As shown in Fig. 1, (I) is composed of five fused rings, with the methoxy group attached to a chiral C atom. The three aromatic rings are almost coplanar, while the six-membered ring adopts a twisted boat conformation, with the methoxy and carbonyl groups pointing in opposite directions from the phenyl plane. Weak intermolecular C—H···O hydrogen bonds formed by phenyl C—H groups and the carbonyl O atoms create racemic dimers which pack along the a axis, as shown in Fig. 2.