Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037530/cf2002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037530/cf2002Isup2.hkl |
CCDC reference: 293847
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C)= 0.004 Å
- R factor = 0.068
- wR factor = 0.145
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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 Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.
C26H23NO | F(000) = 776 |
Mr = 365.45 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3275 reflections |
a = 10.1554 (9) Å | θ = 2.4–21.4° |
b = 16.5088 (15) Å | µ = 0.08 mm−1 |
c = 11.7903 (11) Å | T = 273 K |
β = 97.154 (2)° | Block, colorless |
V = 1961.3 (3) Å3 | 0.21 × 0.13 × 0.08 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2759 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω scans | h = −12→12 |
18504 measured reflections | k = −19→19 |
3437 independent reflections | l = −14→13 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6492P] where P = (Fo2 + 2Fc2)/3 |
3437 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.13 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 | ||
C1 | 0.2912 (2) | 0.25311 (14) | 0.27571 (18) | 0.0406 (6) | |
H1 | 0.2210 | 0.2923 | 0.2511 | 0.049* | |
C3 | 0.3342 (2) | 0.12064 (13) | 0.37012 (19) | 0.0420 (6) | |
H3 | 0.3407 | 0.1137 | 0.4532 | 0.050* | |
C4 | 0.4709 (2) | 0.14989 (15) | 0.3423 (2) | 0.0464 (6) | |
H4 | 0.5401 | 0.1106 | 0.3694 | 0.056* | |
C5 | 0.4990 (2) | 0.23061 (15) | 0.3999 (2) | 0.0468 (6) | |
C6 | 0.4010 (2) | 0.29321 (14) | 0.35494 (18) | 0.0405 (6) | |
C7 | 0.3481 (3) | 0.21810 (16) | 0.1722 (2) | 0.0523 (7) | |
H7A | 0.3767 | 0.2617 | 0.1259 | 0.063* | |
H7B | 0.2803 | 0.1872 | 0.1257 | 0.063* | |
C8 | 0.4662 (3) | 0.16306 (16) | 0.2131 (2) | 0.0554 (7) | |
H8A | 0.4564 | 0.1115 | 0.1736 | 0.067* | |
H8B | 0.5480 | 0.1880 | 0.1964 | 0.067* | |
C9 | 0.1419 (2) | 0.20103 (14) | 0.41199 (18) | 0.0402 (5) | |
C10 | 0.0935 (2) | 0.13700 (16) | 0.4720 (2) | 0.0513 (6) | |
H10 | 0.1250 | 0.0848 | 0.4628 | 0.062* | |
C11 | −0.0009 (3) | 0.15029 (18) | 0.5451 (2) | 0.0636 (8) | |
H11 | −0.0328 | 0.1068 | 0.5836 | 0.076* | |
C12 | −0.0479 (3) | 0.2266 (2) | 0.5615 (3) | 0.0716 (9) | |
H12 | −0.1107 | 0.2353 | 0.6112 | 0.086* | |
C13 | −0.0001 (3) | 0.29031 (19) | 0.5025 (3) | 0.0692 (8) | |
H13 | −0.0309 | 0.3425 | 0.5132 | 0.083* | |
C14 | 0.0925 (2) | 0.27782 (16) | 0.4282 (2) | 0.0520 (7) | |
H14 | 0.1221 | 0.3215 | 0.3885 | 0.062* | |
C15 | 0.2940 (2) | 0.03950 (15) | 0.31577 (19) | 0.0449 (6) | |
C16 | 0.1857 (3) | 0.03093 (16) | 0.2337 (2) | 0.0578 (7) | |
H16 | 0.1355 | 0.0762 | 0.2094 | 0.069* | |
C17 | 0.1506 (3) | −0.04382 (18) | 0.1870 (2) | 0.0688 (8) | |
H17 | 0.0767 | −0.0484 | 0.1323 | 0.083* | |
C18 | 0.2234 (3) | −0.11109 (18) | 0.2204 (3) | 0.0677 (8) | |
H18 | 0.2007 | −0.1612 | 0.1875 | 0.081* | |
C19 | 0.3299 (3) | −0.10405 (18) | 0.3029 (3) | 0.0724 (9) | |
H19 | 0.3792 | −0.1497 | 0.3273 | 0.087* | |
C20 | 0.3643 (3) | −0.02953 (16) | 0.3496 (2) | 0.0644 (8) | |
H20 | 0.4371 | −0.0256 | 0.4056 | 0.077* | |
C21 | 0.4142 (2) | 0.37012 (15) | 0.3876 (2) | 0.0465 (6) | |
H21 | 0.4846 | 0.3804 | 0.4441 | 0.056* | |
C22 | 0.3352 (2) | 0.44092 (14) | 0.3484 (2) | 0.0455 (6) | |
C23 | 0.2799 (3) | 0.45047 (16) | 0.2347 (2) | 0.0583 (7) | |
H23 | 0.2905 | 0.4100 | 0.1818 | 0.070* | |
C24 | 0.2098 (3) | 0.51933 (18) | 0.2006 (3) | 0.0696 (8) | |
H24 | 0.1728 | 0.5248 | 0.1248 | 0.084* | |
C25 | 0.1939 (3) | 0.58008 (18) | 0.2769 (3) | 0.0689 (8) | |
H25 | 0.1463 | 0.6265 | 0.2530 | 0.083* | |
C26 | 0.2485 (3) | 0.57211 (18) | 0.3887 (3) | 0.0651 (8) | |
H26 | 0.2385 | 0.6133 | 0.4407 | 0.078* | |
C27 | 0.3180 (3) | 0.50326 (16) | 0.4240 (2) | 0.0546 (7) | |
H27 | 0.3543 | 0.4984 | 0.5001 | 0.066* | |
N2 | 0.23783 (18) | 0.18577 (11) | 0.33854 (15) | 0.0404 (5) | |
O28 | 0.59236 (18) | 0.24337 (12) | 0.47327 (17) | 0.0696 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0428 (13) | 0.0441 (14) | 0.0347 (12) | 0.0031 (11) | 0.0039 (10) | 0.0016 (10) |
C3 | 0.0471 (14) | 0.0450 (14) | 0.0340 (12) | 0.0062 (11) | 0.0058 (10) | −0.0019 (10) |
C4 | 0.0426 (13) | 0.0507 (15) | 0.0465 (14) | 0.0107 (12) | 0.0078 (11) | −0.0015 (11) |
C5 | 0.0402 (13) | 0.0566 (16) | 0.0437 (14) | 0.0006 (12) | 0.0059 (11) | 0.0005 (12) |
C6 | 0.0422 (13) | 0.0472 (14) | 0.0330 (12) | 0.0018 (11) | 0.0081 (10) | 0.0013 (10) |
C7 | 0.0612 (16) | 0.0630 (17) | 0.0338 (13) | −0.0047 (13) | 0.0102 (11) | −0.0042 (12) |
C8 | 0.0618 (16) | 0.0579 (17) | 0.0504 (15) | 0.0043 (14) | 0.0220 (13) | −0.0056 (13) |
C9 | 0.0342 (12) | 0.0503 (14) | 0.0351 (12) | 0.0036 (11) | 0.0000 (10) | −0.0022 (11) |
C10 | 0.0543 (15) | 0.0519 (16) | 0.0490 (15) | 0.0015 (13) | 0.0111 (12) | 0.0007 (12) |
C11 | 0.0620 (17) | 0.073 (2) | 0.0598 (17) | −0.0012 (15) | 0.0222 (14) | 0.0095 (15) |
C12 | 0.0644 (19) | 0.086 (2) | 0.0702 (19) | 0.0205 (17) | 0.0330 (15) | 0.0082 (17) |
C13 | 0.0668 (18) | 0.071 (2) | 0.0735 (19) | 0.0290 (16) | 0.0225 (16) | 0.0086 (16) |
C14 | 0.0490 (14) | 0.0552 (16) | 0.0537 (15) | 0.0139 (12) | 0.0137 (12) | 0.0069 (12) |
C15 | 0.0516 (15) | 0.0471 (15) | 0.0375 (13) | 0.0042 (12) | 0.0118 (11) | 0.0005 (11) |
C16 | 0.0629 (17) | 0.0522 (17) | 0.0565 (16) | 0.0040 (13) | −0.0004 (14) | −0.0024 (13) |
C17 | 0.078 (2) | 0.0597 (19) | 0.0658 (19) | −0.0081 (16) | −0.0016 (15) | −0.0128 (15) |
C18 | 0.088 (2) | 0.0516 (18) | 0.0662 (19) | −0.0096 (16) | 0.0195 (17) | −0.0135 (15) |
C19 | 0.090 (2) | 0.0475 (18) | 0.078 (2) | 0.0108 (16) | 0.0066 (18) | −0.0004 (15) |
C20 | 0.0727 (19) | 0.0529 (18) | 0.0645 (18) | 0.0090 (15) | −0.0038 (15) | −0.0029 (14) |
C21 | 0.0468 (14) | 0.0542 (16) | 0.0384 (13) | −0.0030 (12) | 0.0048 (11) | −0.0042 (12) |
C22 | 0.0435 (14) | 0.0449 (14) | 0.0492 (15) | −0.0047 (11) | 0.0099 (11) | −0.0034 (11) |
C23 | 0.0733 (19) | 0.0492 (16) | 0.0523 (16) | 0.0014 (14) | 0.0075 (14) | −0.0027 (13) |
C24 | 0.079 (2) | 0.0560 (18) | 0.070 (2) | 0.0007 (16) | −0.0047 (16) | 0.0071 (15) |
C25 | 0.0545 (17) | 0.0500 (18) | 0.102 (2) | 0.0063 (14) | 0.0064 (17) | 0.0010 (17) |
C26 | 0.0539 (17) | 0.0586 (19) | 0.085 (2) | 0.0029 (14) | 0.0176 (16) | −0.0184 (16) |
C27 | 0.0510 (15) | 0.0563 (17) | 0.0582 (16) | −0.0041 (13) | 0.0132 (13) | −0.0113 (13) |
N2 | 0.0415 (11) | 0.0422 (11) | 0.0379 (10) | 0.0058 (9) | 0.0066 (9) | 0.0000 (9) |
O28 | 0.0576 (12) | 0.0722 (13) | 0.0721 (13) | 0.0052 (10) | −0.0197 (10) | −0.0038 (10) |
C1—N2 | 1.476 (3) | C13—C14 | 1.379 (4) |
C1—C6 | 1.515 (3) | C13—H13 | 0.930 |
C1—C7 | 1.527 (3) | C14—H14 | 0.930 |
C1—H1 | 0.980 | C15—C20 | 1.377 (3) |
C3—N2 | 1.470 (3) | C15—C16 | 1.379 (3) |
C3—C15 | 1.519 (3) | C16—C17 | 1.380 (4) |
C3—C4 | 1.544 (3) | C16—H16 | 0.930 |
C3—H3 | 0.980 | C17—C18 | 1.365 (4) |
C4—C5 | 1.506 (3) | C17—H17 | 0.930 |
C4—C8 | 1.534 (3) | C18—C19 | 1.366 (4) |
C4—H4 | 0.980 | C18—H18 | 0.930 |
C5—O28 | 1.220 (3) | C19—C20 | 1.375 (4) |
C5—C6 | 1.486 (3) | C19—H19 | 0.930 |
C6—C21 | 1.329 (3) | C20—H20 | 0.930 |
C7—C8 | 1.534 (4) | C21—C22 | 1.460 (3) |
C7—H7A | 0.970 | C21—H21 | 0.930 |
C7—H7B | 0.970 | C22—C27 | 1.387 (3) |
C8—H8A | 0.970 | C22—C23 | 1.396 (3) |
C8—H8B | 0.970 | C23—C24 | 1.374 (4) |
C9—C14 | 1.385 (3) | C23—H23 | 0.930 |
C9—C10 | 1.395 (3) | C24—C25 | 1.371 (4) |
C9—N2 | 1.404 (3) | C24—H24 | 0.930 |
C10—C11 | 1.383 (4) | C25—C26 | 1.371 (4) |
C10—H10 | 0.930 | C25—H25 | 0.930 |
C11—C12 | 1.369 (4) | C26—C27 | 1.375 (4) |
C11—H11 | 0.930 | C26—H26 | 0.930 |
C12—C13 | 1.382 (4) | C27—H27 | 0.930 |
C12—H12 | 0.930 | ||
N2—C1—C6 | 107.93 (17) | C14—C13—C12 | 121.1 (3) |
N2—C1—C7 | 108.36 (19) | C14—C13—H13 | 119.5 |
C6—C1—C7 | 109.62 (19) | C12—C13—H13 | 119.5 |
N2—C1—H1 | 110.3 | C13—C14—C9 | 120.8 (3) |
C6—C1—H1 | 110.3 | C13—C14—H14 | 119.6 |
C7—C1—H1 | 110.3 | C9—C14—H14 | 119.6 |
N2—C3—C15 | 113.74 (18) | C20—C15—C16 | 117.3 (2) |
N2—C3—C4 | 107.79 (18) | C20—C15—C3 | 120.3 (2) |
C15—C3—C4 | 112.84 (19) | C16—C15—C3 | 122.4 (2) |
N2—C3—H3 | 107.4 | C15—C16—C17 | 121.0 (3) |
C15—C3—H3 | 107.4 | C15—C16—H16 | 119.5 |
C4—C3—H3 | 107.4 | C17—C16—H16 | 119.5 |
C5—C4—C8 | 107.6 (2) | C18—C17—C16 | 120.6 (3) |
C5—C4—C3 | 107.82 (18) | C18—C17—H17 | 119.7 |
C8—C4—C3 | 109.7 (2) | C16—C17—H17 | 119.7 |
C5—C4—H4 | 110.5 | C17—C18—C19 | 119.3 (3) |
C8—C4—H4 | 110.5 | C17—C18—H18 | 120.4 |
C3—C4—H4 | 110.5 | C19—C18—H18 | 120.4 |
O28—C5—C6 | 124.0 (2) | C18—C19—C20 | 120.0 (3) |
O28—C5—C4 | 124.0 (2) | C18—C19—H19 | 120.0 |
C6—C5—C4 | 111.9 (2) | C20—C19—H19 | 120.0 |
C21—C6—C5 | 121.5 (2) | C19—C20—C15 | 121.8 (3) |
C21—C6—C1 | 129.5 (2) | C19—C20—H20 | 119.1 |
C5—C6—C1 | 109.0 (2) | C15—C20—H20 | 119.1 |
C1—C7—C8 | 109.38 (19) | C6—C21—C22 | 129.9 (2) |
C1—C7—H7A | 109.8 | C6—C21—H21 | 115.1 |
C8—C7—H7A | 109.8 | C22—C21—H21 | 115.1 |
C1—C7—H7B | 109.8 | C27—C22—C23 | 117.8 (2) |
C8—C7—H7B | 109.8 | C27—C22—C21 | 119.9 (2) |
H7A—C7—H7B | 108.2 | C23—C22—C21 | 122.3 (2) |
C4—C8—C7 | 108.84 (19) | C24—C23—C22 | 120.4 (3) |
C4—C8—H8A | 109.9 | C24—C23—H23 | 119.8 |
C7—C8—H8A | 109.9 | C22—C23—H23 | 119.8 |
C4—C8—H8B | 109.9 | C25—C24—C23 | 120.8 (3) |
C7—C8—H8B | 109.9 | C25—C24—H24 | 119.6 |
H8A—C8—H8B | 108.3 | C23—C24—H24 | 119.6 |
C14—C9—C10 | 117.8 (2) | C24—C25—C26 | 119.6 (3) |
C14—C9—N2 | 122.7 (2) | C24—C25—H25 | 120.2 |
C10—C9—N2 | 119.5 (2) | C26—C25—H25 | 120.2 |
C11—C10—C9 | 120.7 (2) | C25—C26—C27 | 120.1 (3) |
C11—C10—H10 | 119.6 | C25—C26—H26 | 119.9 |
C9—C10—H10 | 119.6 | C27—C26—H26 | 119.9 |
C12—C11—C10 | 121.0 (3) | C26—C27—C22 | 121.3 (3) |
C12—C11—H11 | 119.5 | C26—C27—H27 | 119.4 |
C10—C11—H11 | 119.5 | C22—C27—H27 | 119.4 |
C11—C12—C13 | 118.6 (3) | C9—N2—C3 | 117.77 (18) |
C11—C12—H12 | 120.7 | C9—N2—C1 | 120.04 (18) |
C13—C12—H12 | 120.7 | C3—N2—C1 | 113.79 (17) |
N2—C3—C4—C5 | 53.2 (2) | C20—C15—C16—C17 | −0.6 (4) |
C15—C3—C4—C5 | 179.59 (19) | C3—C15—C16—C17 | −179.1 (2) |
N2—C3—C4—C8 | −63.8 (2) | C15—C16—C17—C18 | −0.6 (4) |
C15—C3—C4—C8 | 62.7 (2) | C16—C17—C18—C19 | 1.5 (5) |
C8—C4—C5—O28 | −123.6 (3) | C17—C18—C19—C20 | −1.2 (5) |
C3—C4—C5—O28 | 118.2 (3) | C18—C19—C20—C15 | 0.0 (5) |
C8—C4—C5—C6 | 55.3 (2) | C16—C15—C20—C19 | 0.9 (4) |
C3—C4—C5—C6 | −62.9 (2) | C3—C15—C20—C19 | 179.5 (3) |
O28—C5—C6—C21 | 4.5 (4) | C5—C6—C21—C22 | 175.3 (2) |
C4—C5—C6—C21 | −174.4 (2) | C1—C6—C21—C22 | −7.3 (4) |
O28—C5—C6—C1 | −173.4 (2) | C6—C21—C22—C27 | 147.3 (3) |
C4—C5—C6—C1 | 7.7 (3) | C6—C21—C22—C23 | −35.7 (4) |
N2—C1—C6—C21 | −123.8 (3) | C27—C22—C23—C24 | −0.7 (4) |
C7—C1—C6—C21 | 118.4 (3) | C21—C22—C23—C24 | −177.8 (2) |
N2—C1—C6—C5 | 53.8 (2) | C22—C23—C24—C25 | 0.6 (4) |
C7—C1—C6—C5 | −64.0 (2) | C23—C24—C25—C26 | 0.0 (5) |
N2—C1—C7—C8 | −64.4 (2) | C24—C25—C26—C27 | −0.5 (4) |
C6—C1—C7—C8 | 53.1 (3) | C25—C26—C27—C22 | 0.3 (4) |
C5—C4—C8—C7 | −64.8 (3) | C23—C22—C27—C26 | 0.3 (4) |
C3—C4—C8—C7 | 52.2 (3) | C21—C22—C27—C26 | 177.5 (2) |
C1—C7—C8—C4 | 10.1 (3) | C14—C9—N2—C3 | 146.9 (2) |
C14—C9—C10—C11 | 0.1 (4) | C10—C9—N2—C3 | −33.0 (3) |
N2—C9—C10—C11 | 179.9 (2) | C14—C9—N2—C1 | 0.7 (3) |
C9—C10—C11—C12 | −0.8 (4) | C10—C9—N2—C1 | −179.2 (2) |
C10—C11—C12—C13 | 0.6 (5) | C15—C3—N2—C9 | 94.3 (2) |
C11—C12—C13—C14 | 0.3 (5) | C4—C3—N2—C9 | −139.84 (19) |
C12—C13—C14—C9 | −1.1 (4) | C15—C3—N2—C1 | −117.5 (2) |
C10—C9—C14—C13 | 0.9 (4) | C4—C3—N2—C1 | 8.4 (2) |
N2—C9—C14—C13 | −179.0 (2) | C6—C1—N2—C9 | 83.1 (2) |
N2—C3—C15—C20 | −170.8 (2) | C7—C1—N2—C9 | −158.28 (19) |
C4—C3—C15—C20 | 66.0 (3) | C6—C1—N2—C3 | −64.4 (2) |
N2—C3—C15—C16 | 7.7 (3) | C7—C1—N2—C3 | 54.2 (2) |
C4—C3—C15—C16 | −115.5 (3) |
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