Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039389/rz2071sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039389/rz2071Isup2.hkl |
CCDC reference: 624970
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C24H29NO2 | F(000) = 784 |
Mr = 363.48 | Dx = 1.126 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3930 reflections |
a = 10.0061 (12) Å | θ = 2.3–21.2° |
b = 11.5146 (14) Å | µ = 0.07 mm−1 |
c = 18.602 (2) Å | T = 273 K |
V = 2143.3 (4) Å3 | Block, colourless |
Z = 4 | 0.19 × 0.13 × 0.09 mm |
Bruker SMART APEX CCD area-detector diffractometer | 1832 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ω scans | h = −11→11 |
10985 measured reflections | k = −13→13 |
2069 independent reflections | l = −19→20 |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.202P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2069 reflections | Δρmax = 0.11 e Å−3 |
265 parameters | Δρmin = −0.18 e Å−3 |
4 restraints | Absolute structure: Flack (1983), 1532 Friedels pairs |
Primary atom site location: structure-invariant direct methods |
Experimental. 1H NMR (CDCl3): δ 1.55 (s, 3H), 1.65 (s, 3H), 1.89 (d, 1H, J = 12.8 Hz), 2.20–2.60 (m, 3H), 2.75 (dd, 1H, J = 4.5, 12.8 Hz), 2.85 (m, 1H), 3.20 (dd, 1H, J = 9.8, 12.8 Hz), 3.61–3.75 (m, 1H), 3.85 (m, 1H), 5.14 (dd, 2H, J = 8.6, 128 Hz), 5.80 (m, 1H), 7.01 (d, 2H, J = 6.8 Hz), 7.11–7.32 (m, 8H). |
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 | Occ. (<1) | |
O1 | 0.53561 (18) | 0.73286 (14) | 0.79416 (9) | 0.0686 (5) | |
O2 | 0.70312 (18) | 0.80858 (14) | 0.99131 (9) | 0.0685 (5) | |
N1 | 0.61033 (17) | 0.84793 (14) | 0.88289 (10) | 0.0482 (4) | |
C1 | 0.6490 (2) | 0.75085 (19) | 0.93062 (13) | 0.0586 (6) | |
C2 | 0.6435 (3) | 0.9197 (2) | 0.99535 (13) | 0.0654 (7) | |
H2A | 0.6965 | 0.9720 | 1.0247 | 0.079* | |
H2B | 0.5539 | 0.9151 | 1.0151 | 0.079* | |
C3 | 0.6408 (2) | 0.95905 (18) | 0.91781 (12) | 0.0497 (5) | |
H3 | 0.5684 | 1.0150 | 0.9099 | 0.060* | |
C4 | 0.7741 (2) | 1.0089 (2) | 0.89280 (15) | 0.0562 (6) | |
H4A | 0.8456 | 0.9581 | 0.9085 | 0.067* | |
H4B | 0.7754 | 1.0111 | 0.8407 | 0.067* | |
C5 | 0.7989 (2) | 1.12866 (19) | 0.92122 (13) | 0.0546 (6) | |
C6 | 0.7340 (2) | 1.22289 (19) | 0.89251 (15) | 0.0626 (6) | |
H6 | 0.6768 | 1.2121 | 0.8536 | 0.075* | |
C7 | 0.7513 (3) | 1.3327 (2) | 0.91975 (17) | 0.0767 (8) | |
H7 | 0.7047 | 1.3949 | 0.9000 | 0.092* | |
C8 | 0.8366 (4) | 1.3506 (2) | 0.97577 (18) | 0.0910 (10) | |
H8 | 0.8494 | 1.4249 | 0.9941 | 0.109* | |
C9 | 0.9025 (4) | 1.2591 (3) | 1.0044 (2) | 0.1195 (14) | |
H9 | 0.9601 | 1.2705 | 1.0430 | 0.143* | |
C10 | 0.8851 (4) | 1.1494 (2) | 0.9770 (2) | 0.0986 (11) | |
H10 | 0.9330 | 1.0879 | 0.9966 | 0.118* | |
C11 | 0.5534 (2) | 0.83061 (18) | 0.81805 (13) | 0.0520 (5) | |
C12 | 0.5063 (2) | 0.9344 (2) | 0.77493 (13) | 0.0573 (6) | |
H12 | 0.5379 | 1.0060 | 0.7979 | 0.069* | |
C13 | 0.5603 (3) | 0.9283 (3) | 0.69837 (14) | 0.0676 (7) | |
H13A | 0.5399 | 0.8525 | 0.6784 | 0.081* | |
H13B | 0.5151 | 0.9861 | 0.6692 | 0.081* | |
C14 | 0.7080 (3) | 0.9483 (2) | 0.69401 (14) | 0.0626 (6) | |
C15 | 0.7591 (3) | 1.0588 (3) | 0.69392 (15) | 0.0723 (7) | |
H15 | 0.7005 | 1.1215 | 0.6946 | 0.087* | |
C16 | 0.8934 (4) | 1.0795 (4) | 0.69289 (19) | 0.0982 (11) | |
H16 | 0.9259 | 1.1551 | 0.6925 | 0.118* | |
C17 | 0.9789 (4) | 0.9873 (5) | 0.6924 (2) | 0.1218 (15) | |
H17 | 1.0706 | 1.0004 | 0.6929 | 0.146* | |
C18 | 0.9319 (4) | 0.8770 (5) | 0.6912 (3) | 0.1350 (17) | |
H18 | 0.9910 | 0.8147 | 0.6896 | 0.162* | |
C19 | 0.7955 (4) | 0.8576 (3) | 0.6924 (2) | 0.1001 (10) | |
H19 | 0.7632 | 0.7819 | 0.6921 | 0.120* | |
C20 | 0.7597 (3) | 0.6792 (2) | 0.89876 (18) | 0.0832 (9) | |
H20A | 0.7915 | 0.6248 | 0.9340 | 0.125* | |
H20B | 0.8316 | 0.7292 | 0.8843 | 0.125* | |
H20C | 0.7266 | 0.6378 | 0.8577 | 0.125* | |
C21 | 0.5285 (3) | 0.6798 (2) | 0.95281 (17) | 0.0855 (9) | |
H21A | 0.4634 | 0.7296 | 0.9748 | 0.128* | |
H21B | 0.5555 | 0.6211 | 0.9865 | 0.128* | |
H21C | 0.4901 | 0.6435 | 0.9112 | 0.128* | |
C22 | 0.3524 (3) | 0.9341 (3) | 0.77338 (15) | 0.0768 (8) | |
H22A | 0.3232 | 1.0043 | 0.7492 | 0.092* | |
H22B | 0.3237 | 0.8690 | 0.7441 | 0.092* | |
C23 | 0.2799 (8) | 0.9268 (8) | 0.8450 (4) | 0.078 (3) | 0.578 (14) |
H23 | 0.2969 | 0.8633 | 0.8745 | 0.093* | 0.578 (14) |
C24 | 0.1974 (10) | 1.0030 (10) | 0.8666 (6) | 0.120 (4) | 0.578 (14) |
H24A | 0.1787 | 1.0673 | 0.8381 | 0.144* | 0.578 (14) |
H24B | 0.1556 | 0.9945 | 0.9110 | 0.144* | 0.578 (14) |
C23A | 0.2993 (10) | 0.9857 (12) | 0.8426 (5) | 0.085 (4) | 0.422 (14) |
H23A | 0.3208 | 1.0600 | 0.8583 | 0.102* | 0.422 (14) |
C24A | 0.223 (2) | 0.9184 (14) | 0.8768 (8) | 0.146 (7) | 0.422 (14) |
H24C | 0.2048 | 0.8447 | 0.8589 | 0.175* | 0.422 (14) |
H24D | 0.1857 | 0.9424 | 0.9201 | 0.175* | 0.422 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0831 (12) | 0.0529 (9) | 0.0699 (11) | −0.0158 (9) | −0.0081 (9) | −0.0130 (8) |
O2 | 0.0807 (11) | 0.0639 (10) | 0.0609 (11) | 0.0000 (9) | −0.0163 (9) | 0.0069 (8) |
N1 | 0.0515 (10) | 0.0421 (9) | 0.0509 (11) | −0.0014 (8) | −0.0021 (8) | −0.0023 (8) |
C1 | 0.0644 (13) | 0.0494 (12) | 0.0620 (15) | −0.0009 (11) | −0.0053 (13) | 0.0046 (11) |
C2 | 0.0751 (15) | 0.0658 (15) | 0.0555 (16) | −0.0013 (14) | −0.0032 (13) | −0.0048 (12) |
C3 | 0.0526 (12) | 0.0473 (11) | 0.0491 (14) | 0.0037 (10) | −0.0041 (10) | −0.0069 (10) |
C4 | 0.0550 (14) | 0.0534 (12) | 0.0601 (16) | 0.0000 (10) | −0.0035 (11) | −0.0084 (11) |
C5 | 0.0548 (12) | 0.0519 (12) | 0.0570 (14) | −0.0051 (10) | −0.0080 (12) | −0.0022 (10) |
C6 | 0.0686 (15) | 0.0551 (12) | 0.0642 (16) | −0.0087 (11) | −0.0159 (13) | 0.0036 (12) |
C7 | 0.0873 (18) | 0.0526 (13) | 0.090 (2) | −0.0048 (13) | −0.0182 (17) | 0.0082 (13) |
C8 | 0.120 (3) | 0.0523 (15) | 0.100 (2) | −0.0141 (16) | −0.026 (2) | −0.0071 (16) |
C9 | 0.157 (3) | 0.0738 (18) | 0.127 (3) | −0.012 (2) | −0.088 (3) | −0.0119 (18) |
C10 | 0.114 (2) | 0.0596 (16) | 0.122 (3) | 0.0034 (16) | −0.066 (2) | −0.0003 (17) |
C11 | 0.0484 (11) | 0.0545 (13) | 0.0531 (14) | −0.0071 (10) | −0.0003 (10) | −0.0056 (11) |
C12 | 0.0567 (13) | 0.0606 (13) | 0.0548 (15) | −0.0030 (11) | −0.0104 (11) | −0.0028 (11) |
C13 | 0.0749 (17) | 0.0763 (16) | 0.0515 (16) | −0.0054 (14) | −0.0096 (12) | 0.0007 (13) |
C14 | 0.0668 (15) | 0.0740 (16) | 0.0470 (15) | 0.0021 (13) | 0.0009 (11) | 0.0023 (12) |
C15 | 0.0745 (18) | 0.0820 (17) | 0.0604 (18) | −0.0042 (15) | −0.0009 (13) | 0.0048 (14) |
C16 | 0.083 (2) | 0.130 (3) | 0.081 (2) | −0.030 (2) | 0.0013 (17) | 0.016 (2) |
C17 | 0.064 (2) | 0.180 (4) | 0.122 (3) | −0.008 (3) | 0.011 (2) | 0.038 (3) |
C18 | 0.092 (3) | 0.152 (4) | 0.161 (4) | 0.038 (3) | 0.036 (3) | 0.044 (4) |
C19 | 0.098 (2) | 0.089 (2) | 0.114 (3) | 0.0113 (19) | 0.027 (2) | 0.011 (2) |
C20 | 0.0876 (19) | 0.0590 (14) | 0.103 (2) | 0.0194 (14) | −0.0152 (18) | −0.0024 (15) |
C21 | 0.0934 (19) | 0.0775 (18) | 0.086 (2) | −0.0248 (16) | −0.0024 (17) | 0.0197 (16) |
C22 | 0.0588 (14) | 0.105 (2) | 0.0667 (17) | 0.0108 (16) | −0.0122 (13) | −0.0055 (16) |
C23 | 0.058 (4) | 0.101 (6) | 0.073 (5) | −0.012 (4) | 0.003 (3) | −0.010 (4) |
C24 | 0.104 (6) | 0.147 (8) | 0.107 (6) | 0.024 (6) | 0.026 (4) | −0.005 (6) |
C23A | 0.049 (5) | 0.099 (8) | 0.108 (7) | −0.004 (6) | −0.008 (4) | −0.014 (7) |
C24A | 0.145 (13) | 0.178 (15) | 0.114 (10) | −0.017 (13) | 0.056 (9) | 0.029 (10) |
O1—C11 | 1.223 (3) | C13—H13A | 0.9700 |
O2—C2 | 1.414 (3) | C13—H13B | 0.9700 |
O2—C1 | 1.418 (3) | C14—C19 | 1.364 (4) |
N1—C11 | 1.349 (3) | C14—C15 | 1.370 (4) |
N1—C3 | 1.467 (3) | C15—C16 | 1.365 (4) |
N1—C1 | 1.479 (3) | C15—H15 | 0.9300 |
C1—C20 | 1.503 (4) | C16—C17 | 1.363 (6) |
C1—C21 | 1.515 (4) | C16—H16 | 0.9300 |
C2—C3 | 1.512 (3) | C17—C18 | 1.355 (6) |
C2—H2A | 0.9700 | C17—H17 | 0.9300 |
C2—H2B | 0.9700 | C18—C19 | 1.383 (6) |
C3—C4 | 1.525 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9800 | C19—H19 | 0.9300 |
C4—C5 | 1.498 (3) | C20—H20A | 0.9600 |
C4—H4A | 0.9700 | C20—H20B | 0.9600 |
C4—H4B | 0.9700 | C20—H20C | 0.9600 |
C5—C10 | 1.370 (4) | C21—H21A | 0.9600 |
C5—C6 | 1.373 (3) | C21—H21B | 0.9600 |
C6—C7 | 1.373 (3) | C21—H21C | 0.9600 |
C6—H6 | 0.9300 | C22—C23A | 1.513 (8) |
C7—C8 | 1.363 (4) | C22—C23 | 1.519 (7) |
C7—H7 | 0.9300 | C22—H22A | 0.9700 |
C8—C9 | 1.353 (5) | C22—H22B | 0.9700 |
C8—H8 | 0.9300 | C23—C24 | 1.270 (8) |
C9—C10 | 1.373 (4) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—H24A | 0.9300 |
C10—H10 | 0.9300 | C24—H24B | 0.9300 |
C11—C12 | 1.515 (3) | C23A—C24A | 1.259 (10) |
C12—C13 | 1.525 (4) | C23A—H23A | 0.9300 |
C12—C22 | 1.540 (3) | C24A—H24C | 0.9300 |
C12—H12 | 0.9800 | C24A—H24D | 0.9300 |
C13—C14 | 1.498 (4) | ||
C2—O2—C1 | 107.79 (18) | C14—C13—H13A | 109.0 |
C11—N1—C3 | 127.79 (17) | C12—C13—H13A | 109.0 |
C11—N1—C1 | 122.39 (17) | C14—C13—H13B | 109.0 |
C3—N1—C1 | 109.81 (16) | C12—C13—H13B | 109.0 |
O2—C1—N1 | 102.92 (16) | H13A—C13—H13B | 107.8 |
O2—C1—C20 | 106.9 (2) | C19—C14—C15 | 118.1 (3) |
N1—C1—C20 | 111.8 (2) | C19—C14—C13 | 121.1 (3) |
O2—C1—C21 | 109.9 (2) | C15—C14—C13 | 120.7 (3) |
N1—C1—C21 | 111.3 (2) | C16—C15—C14 | 122.0 (3) |
C20—C1—C21 | 113.4 (2) | C16—C15—H15 | 119.0 |
O2—C2—C3 | 103.17 (19) | C14—C15—H15 | 119.0 |
O2—C2—H2A | 111.1 | C17—C16—C15 | 118.8 (4) |
C3—C2—H2A | 111.1 | C17—C16—H16 | 120.6 |
O2—C2—H2B | 111.1 | C15—C16—H16 | 120.6 |
C3—C2—H2B | 111.1 | C18—C17—C16 | 120.8 (4) |
H2A—C2—H2B | 109.1 | C18—C17—H17 | 119.6 |
N1—C3—C2 | 99.49 (17) | C16—C17—H17 | 119.6 |
N1—C3—C4 | 112.01 (18) | C17—C18—C19 | 119.5 (4) |
C2—C3—C4 | 112.9 (2) | C17—C18—H18 | 120.2 |
N1—C3—H3 | 110.7 | C19—C18—H18 | 120.2 |
C2—C3—H3 | 110.7 | C14—C19—C18 | 120.7 (4) |
C4—C3—H3 | 110.7 | C14—C19—H19 | 119.6 |
C5—C4—C3 | 112.6 (2) | C18—C19—H19 | 119.6 |
C5—C4—H4A | 109.1 | C1—C20—H20A | 109.5 |
C3—C4—H4A | 109.1 | C1—C20—H20B | 109.5 |
C5—C4—H4B | 109.1 | H20A—C20—H20B | 109.5 |
C3—C4—H4B | 109.1 | C1—C20—H20C | 109.5 |
H4A—C4—H4B | 107.8 | H20A—C20—H20C | 109.5 |
C10—C5—C6 | 117.0 (2) | H20B—C20—H20C | 109.5 |
C10—C5—C4 | 122.2 (2) | C1—C21—H21A | 109.5 |
C6—C5—C4 | 120.8 (2) | C1—C21—H21B | 109.5 |
C5—C6—C7 | 121.6 (2) | H21A—C21—H21B | 109.5 |
C5—C6—H6 | 119.2 | C1—C21—H21C | 109.5 |
C7—C6—H6 | 119.2 | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 120.0 (3) | H21B—C21—H21C | 109.5 |
C8—C7—H7 | 120.0 | C23A—C22—C12 | 109.5 (5) |
C6—C7—H7 | 120.0 | C23—C22—C12 | 117.5 (4) |
C9—C8—C7 | 119.2 (3) | C23A—C22—H22A | 87.8 |
C9—C8—H8 | 120.4 | C23—C22—H22A | 107.9 |
C7—C8—H8 | 120.4 | C12—C22—H22A | 107.9 |
C8—C9—C10 | 120.6 (3) | C23A—C22—H22B | 132.6 |
C8—C9—H9 | 119.7 | C23—C22—H22B | 107.9 |
C10—C9—H9 | 119.7 | C12—C22—H22B | 107.9 |
C5—C10—C9 | 121.4 (3) | H22A—C22—H22B | 107.2 |
C5—C10—H10 | 119.3 | C24—C23—C22 | 123.4 (11) |
C9—C10—H10 | 119.3 | C24—C23—H23 | 118.3 |
O1—C11—N1 | 121.5 (2) | C22—C23—H23 | 118.3 |
O1—C11—C12 | 119.3 (2) | C23—C24—H24A | 120.0 |
N1—C11—C12 | 119.22 (18) | C23—C24—H24B | 120.0 |
C11—C12—C13 | 110.4 (2) | H24A—C24—H24B | 120.0 |
C11—C12—C22 | 108.6 (2) | C24A—C23A—C22 | 113.7 (15) |
C13—C12—C22 | 109.7 (2) | C24A—C23A—H23A | 123.2 |
C11—C12—H12 | 109.4 | C22—C23A—H23A | 123.2 |
C13—C12—H12 | 109.4 | C23A—C24A—H24C | 120.0 |
C22—C12—H12 | 109.4 | C23A—C24A—H24D | 120.0 |
C14—C13—C12 | 113.1 (2) | H24C—C24A—H24D | 120.0 |
C2—O2—C1—N1 | 26.5 (2) | C3—N1—C11—O1 | 178.5 (2) |
C2—O2—C1—C20 | 144.3 (2) | C1—N1—C11—O1 | −2.9 (3) |
C2—O2—C1—C21 | −92.2 (2) | C3—N1—C11—C12 | −3.5 (3) |
C11—N1—C1—O2 | −179.85 (18) | C1—N1—C11—C12 | 175.0 (2) |
C3—N1—C1—O2 | −1.1 (2) | O1—C11—C12—C13 | −52.3 (3) |
C11—N1—C1—C20 | 65.8 (3) | N1—C11—C12—C13 | 129.7 (2) |
C3—N1—C1—C20 | −115.4 (2) | O1—C11—C12—C22 | 68.0 (3) |
C11—N1—C1—C21 | −62.2 (3) | N1—C11—C12—C22 | −110.1 (2) |
C3—N1—C1—C21 | 116.6 (2) | C11—C12—C13—C14 | −70.1 (3) |
C1—O2—C2—C3 | −41.4 (2) | C22—C12—C13—C14 | 170.3 (2) |
C11—N1—C3—C2 | 156.6 (2) | C12—C13—C14—C19 | 95.8 (3) |
C1—N1—C3—C2 | −22.1 (2) | C12—C13—C14—C15 | −82.0 (3) |
C11—N1—C3—C4 | −83.9 (3) | C19—C14—C15—C16 | −0.6 (5) |
C1—N1—C3—C4 | 97.4 (2) | C13—C14—C15—C16 | 177.3 (3) |
O2—C2—C3—N1 | 37.4 (2) | C14—C15—C16—C17 | −0.4 (6) |
O2—C2—C3—C4 | −81.5 (2) | C15—C16—C17—C18 | 1.6 (7) |
N1—C3—C4—C5 | 173.19 (19) | C16—C17—C18—C19 | −1.7 (8) |
C2—C3—C4—C5 | −75.5 (2) | C15—C14—C19—C18 | 0.4 (6) |
C3—C4—C5—C10 | 103.4 (3) | C13—C14—C19—C18 | −177.4 (4) |
C3—C4—C5—C6 | −75.8 (3) | C17—C18—C19—C14 | 0.7 (8) |
C10—C5—C6—C7 | −2.0 (4) | C11—C12—C22—C23A | 81.1 (6) |
C4—C5—C6—C7 | 177.3 (3) | C13—C12—C22—C23A | −158.2 (6) |
C5—C6—C7—C8 | 1.3 (5) | C11—C12—C22—C23 | 53.0 (5) |
C6—C7—C8—C9 | −0.6 (5) | C13—C12—C22—C23 | 173.6 (5) |
C7—C8—C9—C10 | 0.8 (7) | C23A—C22—C23—C24 | 42.7 (13) |
C6—C5—C10—C9 | 2.1 (5) | C12—C22—C23—C24 | 121.6 (10) |
C4—C5—C10—C9 | −177.2 (4) | C23—C22—C23A—C24A | −9.9 (13) |
C8—C9—C10—C5 | −1.5 (7) | C12—C22—C23A—C24A | −122.4 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13A···O1 | 0.97 | 2.56 | 2.881 (4) | 100 |
C20—H20C···O1 | 0.96 | 2.50 | 3.032 (4) | 115 |
C21—H21C···O1 | 0.96 | 2.45 | 3.015 (4) | 117 |
C4—H4B···Cg1 | 0.97 | 2.88 | 3.815 (2) | 163 |
C2—H2A···Cg1i | 0.97 | 3.23 | 3.896 (2) | 128 |
Symmetry code: (i) −x+3/2, −y+2, z+1/2. |