Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801016087/wn6054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801016087/wn6054Isup2.hkl |
CCDC reference: 175999
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.097
- Data-to-parameter ratio = 19.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -0.400 From the CIF: _refine_ls_abs_structure_Flack_su 0.700 Alert C Flack parameter is too small PLAT_301 Alert C Main Residue Disorder ........................ 4.00 Perc. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.02 From the CIF: _reflns_number_total 9327 Count of symmetry unique reflns 5323 Completeness (_total/calc) 175.22% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4004 Fraction of Friedel pairs measured 0.752 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The title compound, (II), was synthesized from 1,1'-bi-2-naphthol, (I), in n-propanol in the presence of dioxygen under the catalysis of the CuCl2–ethanolamine complex. Compound (II) was isolated as the main product, in a yield of 92%. The single-crystal used for X-ray analysis was recrystallized from acetone. Elemental analysis calculated for C23H18O3 (%): C 80.68, H 5.30; found: C 80.97, H 5.34%; m.p. 422–423 K. νmax: 2959, 2931, 1700 (s, C═O), 1454, 1004, 814 cm-1. δH (500 MHz in CDCl3/TMS): 0.62 (t, J = 7.2 Hz, 3H, –CH3), 1.24–1.38 (m, 2H, –CH2–), 2.81 (t, J = 6.5 Hz, 2H, –OCH2–), 6.26 (d, J = 9.8 Hz, 1H, 2-H), 7.04 (d, J = 7.2 Hz, 1H, 4-H), 7.07 (d, J = 8.5 Hz, 1H, 6-H), 7.16 (d, J = 10.4 Hz, 1H, 3-H), 7.30 (d, J = 9.1 Hz, 1H, 9-H), 7.35 (t, J5H-4H = 7.0 Hz, J6H-5H = 8.5 Hz, 1H, 5-H), 7.38–7.42 (m, 2H, 10-H, 13-H), 7.77–7.80 (m, 1H, 11-H), 7.87 (d, J = 9.1 Hz, 1H, 8-H), 8.14–8.17 (m, 1H, 12-H). δC (125 MHz): 10.65 (CH3), 22.93 (CH2), 66.06 (OCH2), 75.15 (13c-C), 108.31, 116.34, 116.84, 117.20, 123.79, 124.59, 125.65, 126.27, 127.91, 128.10, 130.51, 130.95, 131.74, 132.88, 133.50, 139.00, 151.24, 152.02, 197.91 (C═O). FAB-MS m/z (%): 343 (M++1, 12), 342 (M+, 20), 299 (M+—C3H7, 30), 284 (54), 283 (M+—OC3H7, 100).
The structure was solved by direct methods and all non-H atoms were refined by the full-matrix least-squares method (SHELXTL97) with anisotropic displacement parameters, except for C22 and C23 which are disordered over two positions. The H atoms were placed in calculated positions and refined using a riding model.
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. View of the title structure showing the atomic numbering scheme and displacement ellipsoids at the 50% probability level. |
C23H18O3 | F(000) = 720 |
Mr = 342.37 | Dx = 1.316 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.584 (3) Å | Cell parameters from 5917 reflections |
b = 10.083 (2) Å | θ = 4.2–23.2° |
c = 13.956 (3) Å | µ = 0.09 mm−1 |
β = 102.57 (3)° | T = 293 K |
V = 1728.4 (7) Å3 | Block, yellow |
Z = 4 | 0.41 × 0.30 × 0.25 mm |
CCD diffractometer | 9327 independent reflections |
Radiation source: fine-focus sealed tube | 6047 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.015 |
ϕ and ω scans | θmax = 30.0°, θmin = 4.2° |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | h = −17→17 |
Tmin = 0.965, Tmax = 0.979 | k = −13→14 |
12441 measured reflections | l = −7→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)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0398P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.010 |
9327 reflections | Δρmax = 0.17 e Å−3 |
482 parameters | Δρmin = −0.22 e Å−3 |
16 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.4 (7) |
C23H18O3 | V = 1728.4 (7) Å3 |
Mr = 342.37 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 12.584 (3) Å | µ = 0.09 mm−1 |
b = 10.083 (2) Å | T = 293 K |
c = 13.956 (3) Å | 0.41 × 0.30 × 0.25 mm |
β = 102.57 (3)° |
CCD diffractometer | 9327 independent reflections |
Absorption correction: empirical (using intensity measurements) (Blessing, 1995) | 6047 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.979 | Rint = 0.015 |
12441 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | Δρmax = 0.17 e Å−3 |
S = 1.05 | Δρmin = −0.22 e Å−3 |
9327 reflections | Absolute structure: Flack (1983) |
482 parameters | Absolute structure parameter: −0.4 (7) |
16 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. |
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 | Occ. (<1) | |
C20' | 0.05716 (12) | 0.25837 (16) | 0.72465 (12) | 0.0423 (4) | |
C8' | 0.07005 (12) | 0.47277 (17) | 0.63739 (11) | 0.0429 (4) | |
O2' | 0.09660 (8) | 0.46708 (11) | 0.81448 (8) | 0.0455 (3) | |
O3' | 0.15659 (10) | 0.27599 (12) | 0.59350 (9) | 0.0584 (3) | |
C20 | −0.45331 (13) | 0.76612 (16) | 0.72483 (12) | 0.0440 (4) | |
C8 | −0.50536 (13) | 0.97931 (17) | 0.63593 (12) | 0.0458 (4) | |
C7' | 0.03772 (12) | 0.40607 (15) | 0.72388 (11) | 0.0395 (4) | |
O3 | −0.61601 (10) | 0.78444 (13) | 0.59354 (10) | 0.0608 (3) | |
C14' | 0.04491 (15) | 0.03473 (18) | 0.79227 (14) | 0.0550 (5) | |
C6' | −0.08107 (13) | 0.44930 (17) | 0.71652 (12) | 0.0444 (4) | |
O2 | −0.44428 (9) | 0.97623 (12) | 0.81303 (8) | 0.0511 (3) | |
C7 | −0.43183 (13) | 0.91247 (16) | 0.72276 (12) | 0.0428 (4) | |
C10' | 0.16634 (15) | 0.4734 (2) | 0.50509 (13) | 0.0603 (5) | |
H10A | 0.2060 | 0.4280 | 0.4665 | 0.072* | |
C12' | 0.13812 (16) | 0.0682 (2) | 0.66046 (15) | 0.0614 (5) | |
H12A | 0.1778 | 0.0351 | 0.6168 | 0.074* | |
C18' | −0.02503 (14) | 0.21964 (19) | 0.87074 (13) | 0.0519 (4) | |
H18A | −0.0364 | 0.3102 | 0.8764 | 0.062* | |
O1 | −0.24681 (10) | 0.87211 (14) | 0.70410 (9) | 0.0607 (3) | |
C9 | −0.59411 (14) | 0.91600 (18) | 0.57959 (14) | 0.0514 (4) | |
C6 | −0.31565 (13) | 0.95189 (18) | 0.71468 (12) | 0.0471 (4) | |
C3 | −0.48467 (14) | 1.11145 (18) | 0.61309 (13) | 0.0509 (4) | |
C10 | −0.66625 (15) | 0.9809 (2) | 0.50396 (14) | 0.0628 (5) | |
H10B | −0.7253 | 0.9361 | 0.4660 | 0.075* | |
C4' | −0.03992 (14) | 0.66647 (18) | 0.66421 (13) | 0.0545 (5) | |
H4'A | −0.0508 | 0.7577 | 0.6598 | 0.065* | |
C18 | −0.30159 (15) | 0.7255 (2) | 0.87188 (13) | 0.0556 (5) | |
H18B | −0.2889 | 0.8162 | 0.8798 | 0.067* | |
O1' | −0.15637 (9) | 0.37166 (13) | 0.70526 (9) | 0.0594 (3) | |
C5 | −0.29880 (15) | 1.09645 (19) | 0.71014 (14) | 0.0538 (4) | |
H5A | −0.2329 | 1.1347 | 0.7408 | 0.065* | |
C2' | 0.07980 (15) | 0.6716 (2) | 0.54322 (14) | 0.0593 (5) | |
H2'A | 0.0640 | 0.7610 | 0.5312 | 0.071* | |
C16' | −0.04117 (18) | −0.0014 (2) | 0.92878 (17) | 0.0732 (6) | |
H16A | −0.0652 | −0.0585 | 0.9719 | 0.088* | |
C17' | −0.05611 (17) | 0.1345 (2) | 0.93547 (15) | 0.0659 (6) | |
H17A | −0.0878 | 0.1679 | 0.9848 | 0.079* | |
C11 | −0.54129 (13) | 0.71164 (18) | 0.66147 (13) | 0.0505 (4) | |
C16 | −0.2547 (2) | 0.5016 (2) | 0.92547 (17) | 0.0774 (6) | |
H16B | −0.2091 | 0.4434 | 0.9670 | 0.093* | |
C14 | −0.40812 (16) | 0.54066 (19) | 0.79089 (14) | 0.0565 (5) | |
C3' | 0.04045 (13) | 0.60565 (18) | 0.61596 (12) | 0.0486 (4) | |
C2 | −0.55838 (16) | 1.1779 (2) | 0.54034 (15) | 0.0633 (5) | |
H2A | −0.5472 | 1.2668 | 0.5277 | 0.076* | |
C19 | −0.38703 (13) | 0.67932 (17) | 0.79566 (13) | 0.0486 (4) | |
C11' | 0.11461 (13) | 0.20410 (17) | 0.66166 (13) | 0.0489 (4) | |
C23' | 0.2604 (2) | 0.6743 (2) | 0.8746 (2) | 0.1081 (9) | |
H23A | 0.2987 | 0.7321 | 0.9252 | 0.162* | |
H23B | 0.1852 | 0.7000 | 0.8570 | 0.162* | |
H23C | 0.2919 | 0.6805 | 0.8180 | 0.162* | |
C19' | 0.02437 (13) | 0.17282 (17) | 0.79500 (12) | 0.0458 (4) | |
C12 | −0.56601 (16) | 0.5760 (2) | 0.66003 (16) | 0.0636 (5) | |
H12B | −0.6275 | 0.5433 | 0.6171 | 0.076* | |
C17 | −0.23761 (17) | 0.6385 (2) | 0.93392 (15) | 0.0691 (6) | |
H17B | −0.1814 | 0.6710 | 0.9829 | 0.083* | |
C4 | −0.38010 (15) | 1.17057 (19) | 0.66121 (14) | 0.0566 (5) | |
H4A | −0.3705 | 1.2617 | 0.6574 | 0.068* | |
C9' | 0.13049 (14) | 0.40843 (18) | 0.58052 (13) | 0.0490 (4) | |
C5' | −0.09748 (14) | 0.59395 (18) | 0.71410 (13) | 0.0520 (4) | |
H5'A | −0.1466 | 0.6333 | 0.7465 | 0.062* | |
C13' | 0.10304 (16) | −0.01378 (19) | 0.72262 (16) | 0.0662 (5) | |
H13A | 0.1169 | −0.1042 | 0.7202 | 0.079* | |
C21' | 0.21110 (14) | 0.4387 (2) | 0.83746 (15) | 0.0599 (5) | |
H21A | 0.2396 | 0.4440 | 0.7783 | 0.072* | |
H21B | 0.2233 | 0.3495 | 0.8635 | 0.072* | |
C13 | −0.49952 (18) | 0.4934 (2) | 0.72171 (16) | 0.0671 (6) | |
H13B | −0.5142 | 0.4029 | 0.7186 | 0.081* | |
C15 | −0.33852 (19) | 0.4553 (2) | 0.85602 (17) | 0.0734 (6) | |
H15A | −0.3507 | 0.3643 | 0.8510 | 0.088* | |
C22' | 0.26860 (17) | 0.5357 (2) | 0.91107 (17) | 0.0746 (6) | |
H22A | 0.2384 | 0.5308 | 0.9692 | 0.089* | |
H22B | 0.3448 | 0.5112 | 0.9300 | 0.089* | |
C1 | −0.64830 (17) | 1.1122 (2) | 0.48668 (15) | 0.0670 (6) | |
H1A | −0.6973 | 1.1576 | 0.4382 | 0.080* | |
C15' | 0.00833 (17) | −0.0509 (2) | 0.85961 (16) | 0.0686 (6) | |
H15B | 0.0186 | −0.1420 | 0.8560 | 0.082* | |
C1' | 0.14227 (16) | 0.6046 (2) | 0.48891 (15) | 0.0654 (5) | |
H1'A | 0.1683 | 0.6496 | 0.4406 | 0.079* | |
C21 | −0.54955 (18) | 0.9626 (2) | 0.83509 (18) | 0.0807 (7) | |
H21C | −0.5613 | 0.8708 | 0.8507 | 0.097* | |
H21D | −0.6051 | 0.9872 | 0.7781 | 0.097* | |
C22 | −0.5588 (4) | 1.0456 (5) | 0.9169 (3) | 0.0635 (12) | 0.50 |
H22C | −0.6352 | 1.0432 | 0.9191 | 0.076* | 0.50 |
H22D | −0.5207 | 0.9981 | 0.9747 | 0.076* | 0.50 |
C23 | −0.5283 (4) | 1.1755 (6) | 0.9335 (4) | 0.0778 (14) | 0.50 |
H23D | −0.5451 | 1.2045 | 0.9940 | 0.117* | 0.50 |
H23E | −0.5670 | 1.2293 | 0.8805 | 0.117* | 0.50 |
H23F | −0.4514 | 1.1836 | 0.9376 | 0.117* | 0.50 |
C22" | −0.5962 (4) | 1.1026 (9) | 0.8500 (5) | 0.118 (3) | 0.50 |
H22E | −0.6326 | 1.1299 | 0.7844 | 0.142* | 0.50 |
H22F | −0.6541 | 1.0849 | 0.8843 | 0.142* | 0.50 |
C23" | −0.5574 (9) | 1.1951 (10) | 0.8847 (7) | 0.152 (4)* | 0.50 |
H23G | −0.6112 | 1.2639 | 0.8787 | 0.228* | 0.50 |
H23H | −0.5010 | 1.2222 | 0.8525 | 0.228* | 0.50 |
H23I | −0.5267 | 1.1790 | 0.9529 | 0.228* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C20' | 0.0369 (8) | 0.0420 (9) | 0.0455 (9) | −0.0050 (7) | 0.0036 (7) | −0.0050 (7) |
C8' | 0.0374 (8) | 0.0461 (10) | 0.0432 (9) | −0.0063 (8) | 0.0049 (7) | −0.0015 (7) |
O2' | 0.0412 (6) | 0.0461 (6) | 0.0462 (6) | −0.0018 (5) | 0.0034 (5) | −0.0084 (5) |
O3' | 0.0583 (8) | 0.0578 (8) | 0.0644 (8) | 0.0022 (6) | 0.0248 (7) | −0.0050 (6) |
C20 | 0.0388 (8) | 0.0456 (10) | 0.0487 (10) | −0.0044 (7) | 0.0119 (7) | −0.0063 (8) |
C8 | 0.0418 (9) | 0.0481 (10) | 0.0485 (9) | 0.0018 (8) | 0.0124 (7) | −0.0048 (8) |
C7' | 0.0373 (8) | 0.0382 (9) | 0.0424 (9) | −0.0037 (7) | 0.0074 (7) | −0.0063 (7) |
O3 | 0.0445 (7) | 0.0582 (8) | 0.0728 (9) | −0.0060 (6) | −0.0024 (6) | −0.0075 (7) |
C14' | 0.0492 (10) | 0.0473 (11) | 0.0628 (12) | −0.0010 (8) | −0.0001 (9) | 0.0011 (9) |
C6' | 0.0406 (9) | 0.0486 (10) | 0.0434 (9) | −0.0018 (8) | 0.0080 (7) | −0.0003 (8) |
O2 | 0.0489 (6) | 0.0548 (7) | 0.0533 (7) | −0.0081 (6) | 0.0193 (5) | −0.0119 (6) |
C7 | 0.0379 (8) | 0.0424 (9) | 0.0494 (10) | −0.0047 (7) | 0.0121 (7) | −0.0081 (7) |
C10' | 0.0516 (10) | 0.0797 (15) | 0.0530 (11) | −0.0110 (11) | 0.0188 (8) | −0.0025 (11) |
C12' | 0.0596 (12) | 0.0539 (12) | 0.0722 (13) | 0.0074 (9) | 0.0178 (10) | −0.0116 (10) |
C18' | 0.0523 (10) | 0.0524 (11) | 0.0487 (10) | −0.0040 (8) | 0.0058 (8) | 0.0004 (8) |
O1 | 0.0467 (7) | 0.0631 (8) | 0.0759 (9) | 0.0055 (6) | 0.0217 (6) | −0.0004 (7) |
C9 | 0.0434 (9) | 0.0526 (11) | 0.0582 (11) | 0.0012 (8) | 0.0112 (8) | −0.0030 (8) |
C6 | 0.0423 (9) | 0.0528 (11) | 0.0468 (9) | −0.0052 (8) | 0.0109 (7) | −0.0049 (8) |
C3 | 0.0495 (10) | 0.0487 (10) | 0.0580 (11) | 0.0004 (8) | 0.0192 (9) | −0.0010 (9) |
C10 | 0.0470 (10) | 0.0781 (15) | 0.0600 (12) | 0.0086 (10) | 0.0042 (9) | −0.0031 (11) |
C4' | 0.0504 (10) | 0.0442 (10) | 0.0662 (12) | 0.0031 (9) | 0.0065 (9) | 0.0019 (9) |
C18 | 0.0525 (10) | 0.0624 (12) | 0.0521 (11) | −0.0029 (9) | 0.0115 (8) | −0.0012 (9) |
O1' | 0.0398 (7) | 0.0600 (8) | 0.0763 (9) | −0.0075 (6) | 0.0083 (6) | 0.0023 (7) |
C5 | 0.0470 (10) | 0.0531 (11) | 0.0635 (11) | −0.0139 (9) | 0.0168 (9) | −0.0038 (9) |
C2' | 0.0545 (11) | 0.0585 (11) | 0.0610 (12) | −0.0073 (10) | 0.0042 (9) | 0.0148 (10) |
C16' | 0.0765 (14) | 0.0689 (15) | 0.0717 (14) | −0.0103 (12) | 0.0105 (12) | 0.0250 (12) |
C17' | 0.0697 (13) | 0.0744 (15) | 0.0532 (11) | −0.0083 (11) | 0.0124 (10) | 0.0094 (10) |
C11 | 0.0425 (9) | 0.0494 (10) | 0.0587 (11) | −0.0044 (8) | 0.0091 (8) | −0.0068 (9) |
C16 | 0.0762 (15) | 0.0768 (17) | 0.0764 (15) | 0.0174 (12) | 0.0108 (12) | 0.0238 (12) |
C14 | 0.0621 (12) | 0.0498 (11) | 0.0604 (12) | −0.0026 (9) | 0.0194 (9) | 0.0017 (9) |
C3' | 0.0433 (9) | 0.0490 (10) | 0.0502 (10) | −0.0057 (8) | 0.0030 (8) | 0.0035 (8) |
C2 | 0.0639 (12) | 0.0609 (12) | 0.0686 (12) | 0.0099 (11) | 0.0219 (10) | 0.0106 (10) |
C19 | 0.0473 (10) | 0.0497 (11) | 0.0514 (10) | −0.0035 (8) | 0.0167 (8) | −0.0027 (8) |
C11' | 0.0441 (9) | 0.0476 (11) | 0.0546 (11) | −0.0011 (8) | 0.0099 (8) | −0.0041 (8) |
C23' | 0.0972 (19) | 0.0662 (17) | 0.158 (3) | −0.0257 (15) | 0.0214 (18) | −0.0118 (17) |
C19' | 0.0415 (9) | 0.0432 (10) | 0.0486 (10) | −0.0045 (8) | 0.0011 (7) | −0.0010 (8) |
C12 | 0.0549 (11) | 0.0533 (12) | 0.0798 (14) | −0.0147 (10) | 0.0086 (10) | −0.0141 (10) |
C17 | 0.0631 (13) | 0.0854 (17) | 0.0560 (12) | 0.0020 (11) | 0.0069 (10) | 0.0074 (11) |
C4 | 0.0582 (12) | 0.0463 (11) | 0.0694 (13) | −0.0042 (9) | 0.0227 (10) | −0.0001 (9) |
C9' | 0.0402 (9) | 0.0531 (11) | 0.0527 (11) | −0.0048 (8) | 0.0079 (8) | −0.0044 (8) |
C5' | 0.0441 (9) | 0.0497 (11) | 0.0620 (11) | 0.0057 (8) | 0.0112 (8) | −0.0051 (9) |
C13' | 0.0617 (12) | 0.0431 (11) | 0.0886 (15) | 0.0068 (10) | 0.0055 (11) | −0.0065 (11) |
C21' | 0.0435 (10) | 0.0576 (12) | 0.0709 (12) | 0.0018 (9) | −0.0040 (8) | −0.0075 (10) |
C13 | 0.0735 (13) | 0.0445 (11) | 0.0847 (15) | −0.0126 (10) | 0.0200 (12) | −0.0076 (10) |
C15 | 0.0892 (16) | 0.0514 (12) | 0.0829 (15) | 0.0066 (12) | 0.0260 (13) | 0.0112 (12) |
C22' | 0.0532 (12) | 0.0764 (15) | 0.0844 (15) | −0.0028 (11) | −0.0061 (11) | −0.0156 (12) |
C1 | 0.0593 (12) | 0.0770 (16) | 0.0626 (12) | 0.0174 (11) | 0.0089 (10) | 0.0116 (11) |
C15' | 0.0710 (13) | 0.0492 (12) | 0.0786 (14) | −0.0048 (10) | 0.0009 (11) | 0.0155 (11) |
C1' | 0.0583 (12) | 0.0801 (16) | 0.0585 (12) | −0.0141 (11) | 0.0142 (9) | 0.0154 (11) |
C21 | 0.0723 (14) | 0.0816 (16) | 0.1032 (18) | −0.0206 (13) | 0.0517 (13) | −0.0210 (14) |
C22 | 0.062 (3) | 0.090 (3) | 0.042 (2) | 0.009 (2) | 0.0183 (19) | −0.004 (2) |
C23 | 0.074 (3) | 0.079 (4) | 0.080 (4) | 0.012 (3) | 0.017 (3) | −0.024 (3) |
C22" | 0.044 (3) | 0.201 (7) | 0.114 (5) | −0.012 (4) | 0.026 (3) | −0.085 (5) |
C20'—C11' | 1.368 (2) | C18'—C17' | 1.364 (3) |
C20'—C19' | 1.433 (2) | C18'—C19' | 1.419 (2) |
C20'—C7' | 1.509 (2) | O1—C6 | 1.214 (2) |
C8'—C9' | 1.376 (2) | C9—C10 | 1.396 (3) |
C8'—C3' | 1.405 (2) | C6—C5 | 1.476 (3) |
C8'—C7' | 1.513 (2) | C3—C2 | 1.389 (3) |
O2'—C21' | 1.435 (2) | C3—C4 | 1.467 (2) |
O2'—C7' | 1.4554 (18) | C10—C1 | 1.373 (3) |
O3'—C9' | 1.378 (2) | C4'—C5' | 1.328 (2) |
O3'—C11' | 1.389 (2) | C4'—C3' | 1.466 (2) |
C20—C11 | 1.372 (2) | C18—C17 | 1.366 (3) |
C20—C19 | 1.442 (2) | C18—C19 | 1.417 (2) |
C20—C7 | 1.502 (2) | C5—C4 | 1.329 (3) |
C8—C9 | 1.375 (2) | C2'—C1' | 1.381 (3) |
C8—C3 | 1.407 (2) | C2'—C3' | 1.392 (2) |
C8—C7 | 1.514 (2) | C16'—C15' | 1.353 (3) |
C7'—C6' | 1.539 (2) | C16'—C17' | 1.389 (3) |
O3—C9 | 1.377 (2) | C11—C12 | 1.402 (3) |
O3—C11 | 1.391 (2) | C16—C15 | 1.351 (3) |
C14'—C19' | 1.418 (2) | C16—C17 | 1.397 (3) |
C14'—C13' | 1.424 (3) | C14—C15 | 1.410 (3) |
C14'—C15' | 1.424 (3) | C14—C13 | 1.414 (3) |
C6'—O1' | 1.2126 (19) | C14—C19 | 1.422 (2) |
C6'—C5' | 1.472 (2) | C2—C1 | 1.382 (3) |
O2—C21 | 1.430 (2) | C23'—C22' | 1.483 (3) |
O2—C7 | 1.4529 (19) | C12—C13 | 1.349 (3) |
C7—C6 | 1.543 (2) | C21'—C22' | 1.487 (3) |
C10'—C1' | 1.366 (3) | C21—C22 | 1.441 (5) |
C10'—C9' | 1.395 (2) | C21—C22" | 1.560 (8) |
C12'—C13' | 1.341 (3) | C22—C23 | 1.370 (6) |
C12'—C11' | 1.403 (3) | C22"—C23" | 1.114 (9) |
C11'—C20'—C19' | 118.08 (15) | C5'—C4'—C3' | 121.34 (17) |
C11'—C20'—C7' | 119.85 (15) | C17—C18—C19 | 120.72 (19) |
C19'—C20'—C7' | 121.90 (14) | C4—C5—C6 | 118.39 (17) |
C9'—C8'—C3' | 118.76 (15) | C1'—C2'—C3' | 120.11 (19) |
C9'—C8'—C7' | 121.95 (15) | C15'—C16'—C17' | 120.1 (2) |
C3'—C8'—C7' | 119.26 (14) | C18'—C17'—C16' | 120.9 (2) |
C21'—O2'—C7' | 113.99 (12) | C20—C11—O3 | 123.99 (16) |
C9'—O3'—C11' | 118.73 (13) | C20—C11—C12 | 123.04 (17) |
C11—C20—C19 | 117.64 (15) | O3—C11—C12 | 112.97 (15) |
C11—C20—C7 | 120.29 (15) | C15—C16—C17 | 119.0 (2) |
C19—C20—C7 | 121.99 (14) | C15—C14—C13 | 122.23 (19) |
C9—C8—C3 | 118.50 (16) | C15—C14—C19 | 119.13 (19) |
C9—C8—C7 | 122.01 (16) | C13—C14—C19 | 118.63 (18) |
C3—C8—C7 | 119.46 (14) | C2'—C3'—C8' | 119.41 (17) |
O2'—C7'—C20' | 111.09 (13) | C2'—C3'—C4' | 121.71 (17) |
O2'—C7'—C8' | 109.32 (12) | C8'—C3'—C4' | 118.59 (15) |
C20'—C7'—C8' | 111.91 (13) | C1—C2—C3 | 120.2 (2) |
O2'—C7'—C6' | 103.99 (12) | C18—C19—C14 | 117.52 (17) |
C20'—C7'—C6' | 115.70 (13) | C18—C19—C20 | 123.11 (16) |
C8'—C7'—C6' | 104.29 (13) | C14—C19—C20 | 119.36 (16) |
C9—O3—C11 | 118.58 (13) | C20'—C11'—O3' | 124.37 (15) |
C19'—C14'—C13' | 118.64 (18) | C20'—C11'—C12' | 122.73 (17) |
C19'—C14'—C15' | 119.37 (19) | O3'—C11'—C12' | 112.90 (16) |
C13'—C14'—C15' | 121.99 (18) | C18'—C19'—C14' | 117.31 (17) |
O1'—C6'—C5' | 122.33 (15) | C18'—C19'—C20' | 123.24 (16) |
O1'—C6'—C7' | 123.10 (15) | C14'—C19'—C20' | 119.41 (16) |
C5'—C6'—C7' | 114.29 (14) | C13—C12—C11 | 119.21 (18) |
C21—O2—C7 | 115.07 (13) | C18—C17—C16 | 121.5 (2) |
O2—C7—C20 | 111.37 (13) | C5—C4—C3 | 121.32 (18) |
O2—C7—C8 | 109.55 (13) | O3'—C9'—C8' | 121.82 (16) |
C20—C7—C8 | 111.82 (14) | O3'—C9'—C10' | 116.56 (17) |
O2—C7—C6 | 103.42 (12) | C8'—C9'—C10' | 121.61 (17) |
C20—C7—C6 | 115.60 (14) | C4'—C5'—C6' | 117.88 (17) |
C8—C7—C6 | 104.52 (13) | C12'—C13'—C14' | 121.35 (18) |
C1'—C10'—C9' | 118.88 (18) | O2'—C21'—C22' | 109.73 (16) |
C13'—C12'—C11' | 119.63 (18) | C12—C13—C14 | 121.81 (18) |
C17'—C18'—C19' | 121.28 (18) | C16—C15—C14 | 122.0 (2) |
O3—C9—C8 | 121.93 (16) | C23'—C22'—C21' | 113.3 (2) |
O3—C9—C10 | 116.18 (17) | C10—C1—C2 | 120.88 (19) |
C8—C9—C10 | 121.88 (18) | C16'—C15'—C14' | 120.8 (2) |
O1—C6—C5 | 122.40 (16) | C10'—C1'—C2' | 121.03 (19) |
O1—C6—C7 | 123.41 (16) | O2—C21—C22 | 110.7 (2) |
C5—C6—C7 | 113.88 (15) | O2—C21—C22" | 109.6 (3) |
C2—C3—C8 | 119.67 (17) | C22—C21—C22" | 43.2 (3) |
C2—C3—C4 | 121.88 (18) | C23—C22—C21 | 128.4 (4) |
C8—C3—C4 | 118.20 (16) | C23"—C22"—C21 | 132.4 (7) |
C1—C10—C9 | 118.68 (19) | ||
C21'—O2'—C7'—C20' | 54.27 (18) | C8—C3—C2—C1 | −3.8 (3) |
C21'—O2'—C7'—C8' | −69.71 (17) | C4—C3—C2—C1 | 170.42 (17) |
C21'—O2'—C7'—C6' | 179.37 (14) | C17—C18—C19—C14 | 4.4 (3) |
C11'—C20'—C7'—O2' | −112.36 (16) | C17—C18—C19—C20 | −176.57 (17) |
C19'—C20'—C7'—O2' | 62.74 (18) | C15—C14—C19—C18 | −5.2 (3) |
C11'—C20'—C7'—C8' | 10.1 (2) | C13—C14—C19—C18 | 173.87 (17) |
C19'—C20'—C7'—C8' | −174.76 (13) | C15—C14—C19—C20 | 175.72 (16) |
C11'—C20'—C7'—C6' | 129.40 (16) | C13—C14—C19—C20 | −5.2 (3) |
C19'—C20'—C7'—C6' | −55.5 (2) | C11—C20—C19—C18 | −172.76 (16) |
C9'—C8'—C7'—O2' | 110.82 (16) | C7—C20—C19—C18 | 4.0 (2) |
C3'—C8'—C7'—O2' | −67.24 (17) | C11—C20—C19—C14 | 6.3 (2) |
C9'—C8'—C7'—C20' | −12.7 (2) | C7—C20—C19—C14 | −176.94 (16) |
C3'—C8'—C7'—C20' | 169.26 (13) | C19'—C20'—C11'—O3' | −176.39 (14) |
C9'—C8'—C7'—C6' | −138.47 (15) | C7'—C20'—C11'—O3' | −1.1 (2) |
C3'—C8'—C7'—C6' | 43.47 (18) | C19'—C20'—C11'—C12' | 2.9 (2) |
O2'—C7'—C6'—O1' | −127.00 (16) | C7'—C20'—C11'—C12' | 178.20 (16) |
C20'—C7'—C6'—O1' | −4.9 (2) | C9'—O3'—C11'—C20' | −6.8 (2) |
C8'—C7'—C6'—O1' | 118.46 (17) | C9'—O3'—C11'—C12' | 173.84 (16) |
O2'—C7'—C6'—C5' | 58.98 (17) | C13'—C12'—C11'—C20' | 0.4 (3) |
C20'—C7'—C6'—C5' | −178.92 (15) | C13'—C12'—C11'—O3' | 179.78 (17) |
C8'—C7'—C6'—C5' | −55.56 (18) | C17'—C18'—C19'—C14' | −3.0 (2) |
C21—O2—C7—C20 | −59.2 (2) | C17'—C18'—C19'—C20' | 179.24 (16) |
C21—O2—C7—C8 | 65.04 (19) | C13'—C14'—C19'—C18' | −174.52 (16) |
C21—O2—C7—C6 | 176.04 (16) | C15'—C14'—C19'—C18' | 4.7 (2) |
C11—C20—C7—O2 | 114.07 (17) | C13'—C14'—C19'—C20' | 3.3 (2) |
C19—C20—C7—O2 | −62.60 (19) | C15'—C14'—C19'—C20' | −177.45 (15) |
C11—C20—C7—C8 | −8.9 (2) | C11'—C20'—C19'—C18' | 173.00 (15) |
C19—C20—C7—C8 | 174.46 (14) | C7'—C20'—C19'—C18' | −2.2 (2) |
C11—C20—C7—C6 | −128.30 (16) | C11'—C20'—C19'—C14' | −4.7 (2) |
C19—C20—C7—C6 | 55.0 (2) | C7'—C20'—C19'—C14' | −179.92 (15) |
C9—C8—C7—O2 | −111.78 (17) | C20—C11—C12—C13 | −1.7 (3) |
C3—C8—C7—O2 | 66.51 (18) | O3—C11—C12—C13 | 179.37 (17) |
C9—C8—C7—C20 | 12.2 (2) | C19—C18—C17—C16 | −0.8 (3) |
C3—C8—C7—C20 | −169.52 (14) | C15—C16—C17—C18 | −2.0 (3) |
C9—C8—C7—C6 | 137.95 (16) | C6—C5—C4—C3 | 0.4 (3) |
C3—C8—C7—C6 | −43.76 (19) | C2—C3—C4—C5 | −161.69 (18) |
C11—O3—C9—C8 | −5.1 (2) | C8—C3—C4—C5 | 12.6 (3) |
C11—O3—C9—C10 | 173.96 (16) | C11'—O3'—C9'—C8' | 4.2 (2) |
C3—C8—C9—O3 | 176.02 (16) | C11'—O3'—C9'—C10' | −174.32 (14) |
C7—C8—C9—O3 | −5.7 (2) | C3'—C8'—C9'—O3' | −175.92 (15) |
C3—C8—C9—C10 | −3.0 (3) | C7'—C8'—C9'—O3' | 6.0 (2) |
C7—C8—C9—C10 | 175.32 (16) | C3'—C8'—C9'—C10' | 2.5 (2) |
O2—C7—C6—O1 | 126.68 (17) | C7'—C8'—C9'—C10' | −175.53 (15) |
C20—C7—C6—O1 | 4.7 (2) | C1'—C10'—C9'—O3' | 179.77 (16) |
C8—C7—C6—O1 | −118.66 (18) | C1'—C10'—C9'—C8' | 1.2 (3) |
O2—C7—C6—C5 | −59.60 (18) | C3'—C4'—C5'—C6' | −2.2 (3) |
C20—C7—C6—C5 | 178.42 (15) | O1'—C6'—C5'—C4' | −136.00 (18) |
C8—C7—C6—C5 | 55.06 (18) | C7'—C6'—C5'—C4' | 38.1 (2) |
C9—C8—C3—C2 | 5.3 (2) | C11'—C12'—C13'—C14' | −1.9 (3) |
C7—C8—C3—C2 | −173.06 (16) | C19'—C14'—C13'—C12' | 0.0 (3) |
C9—C8—C3—C4 | −169.13 (15) | C15'—C14'—C13'—C12' | −179.19 (18) |
C7—C8—C3—C4 | 12.5 (2) | C7'—O2'—C21'—C22' | 162.47 (16) |
O3—C9—C10—C1 | −179.94 (17) | C11—C12—C13—C14 | 2.9 (3) |
C8—C9—C10—C1 | −0.9 (3) | C15—C14—C13—C12 | 179.63 (19) |
O1—C6—C5—C4 | 137.16 (19) | C19—C14—C13—C12 | 0.6 (3) |
C7—C6—C5—C4 | −36.6 (2) | C17—C16—C15—C14 | 1.0 (3) |
C19'—C18'—C17'—C16' | −0.5 (3) | C13—C14—C15—C16 | −176.4 (2) |
C15'—C16'—C17'—C18' | 2.4 (3) | C19—C14—C15—C16 | 2.6 (3) |
C19—C20—C11—O3 | 175.92 (15) | O2'—C21'—C22'—C23' | −63.2 (3) |
C7—C20—C11—O3 | −0.9 (2) | C9—C10—C1—C2 | 2.5 (3) |
C19—C20—C11—C12 | −2.9 (3) | C3—C2—C1—C10 | −0.2 (3) |
C7—C20—C11—C12 | −179.72 (17) | C17'—C16'—C15'—C14' | −0.6 (3) |
C9—O3—C11—C20 | 8.6 (2) | C19'—C14'—C15'—C16' | −3.0 (3) |
C9—O3—C11—C12 | −172.50 (16) | C13'—C14'—C15'—C16' | 176.14 (19) |
C1'—C2'—C3'—C8' | 3.7 (3) | C9'—C10'—C1'—C2' | −2.6 (3) |
C1'—C2'—C3'—C4' | −170.06 (17) | C3'—C2'—C1'—C10' | 0.2 (3) |
C9'—C8'—C3'—C2' | −4.9 (2) | C7—O2—C21—C22 | −171.1 (2) |
C7'—C8'—C3'—C2' | 173.18 (15) | C7—O2—C21—C22" | −125.0 (3) |
C9'—C8'—C3'—C4' | 168.97 (15) | O2—C21—C22—C23 | 45.6 (6) |
C7'—C8'—C3'—C4' | −12.9 (2) | C22"—C21—C22—C23 | −51.4 (5) |
C5'—C4'—C3'—C2' | 162.62 (17) | O2—C21—C22"—C23" | −37.6 (13) |
C5'—C4'—C3'—C8' | −11.1 (3) | C22—C21—C22"—C23" | 62.1 (10) |
Experimental details
Crystal data | |
Chemical formula | C23H18O3 |
Mr | 342.37 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 12.584 (3), 10.083 (2), 13.956 (3) |
β (°) | 102.57 (3) |
V (Å3) | 1728.4 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.41 × 0.30 × 0.25 |
Data collection | |
Diffractometer | CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (Blessing, 1995) |
Tmin, Tmax | 0.965, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12441, 9327, 6047 |
Rint | 0.015 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.097, 1.05 |
No. of reflections | 9327 |
No. of parameters | 482 |
No. of restraints | 16 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.22 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −0.4 (7) |
Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
C20'—C7' | 1.509 (2) | C8—C7 | 1.514 (2) |
C8'—C7' | 1.513 (2) | C7'—C6' | 1.539 (2) |
O2'—C21' | 1.435 (2) | O2—C21 | 1.430 (2) |
O2'—C7' | 1.4554 (18) | O2—C7 | 1.4529 (19) |
C20—C7 | 1.502 (2) | C7—C6 | 1.543 (2) |
C21'—O2'—C7' | 113.99 (12) | C21—O2—C7 | 115.07 (13) |
O2'—C7'—C20' | 111.09 (13) | O2—C7—C20 | 111.37 (13) |
O2'—C7'—C8' | 109.32 (12) | O2—C7—C8 | 109.55 (13) |
C20'—C7'—C8' | 111.91 (13) | C20—C7—C8 | 111.82 (14) |
O2'—C7'—C6' | 103.99 (12) | O2—C7—C6 | 103.42 (12) |
C20'—C7'—C6' | 115.70 (13) | C20—C7—C6 | 115.60 (14) |
C8'—C7'—C6' | 104.29 (13) | C8—C7—C6 | 104.52 (13) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
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It is well known that most biological reactions are catalysed by enzymes under mild conditions, with high efficiency and selectivity. It is interesting to develop small molecules or complexes as catalysts to mimic some aspect of enzyme function in organic reactions, especially in the synthesis of structurally complicated compounds. Copper–amine complexes have been frequently used to mimic oxidases (Liang et al., 1999; Mahadevan et al., 2000) since many oxidases contained copper in their active sites (McGuirl & Dooley, 1999). Catalytic oxidation using dioxygen as sole oxidant was believed to be environmentally friendly since the resulting product was water (Choudary et al., 2000). Successful application of copper–amine complexes in aerobic oxidative synthesis had been reported (Marko et al., 1996; Nakajima et al., 1999; Tan et al., 2001). In our work, similar to that of Nakajima et al. (1999), the complex of CuCl2–ethanolamine (Tan et al., 2001) in n-propanol led to a domino reaction from 1,1'-bi-2-naphthol, (I), to yield the title compound, (II), a racemic multicyclic unsaturated ketone containing an n-propoxy group derived from the solvent n-propanol. The reaction could even take place at room temperature in high yield. Three conversions occurred from (I) to (II), i.e. 2'-O—C8 coupling, 2-OH oxidation and C1–OCH2CH2CH3 coupling. The racemic structure of (II) was confirmed by 1H NMR, 13C NMR, IR, FAB–MS and elemental analysis, further confirmed by this single-crystal X-ray analysis.
As shown in Fig. 1, the molecule is composed of five fused rings with the propoxy group attached to a chiral C atom. The geometries of the two molecules show no unexpected features.