Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680201125X/ya6104sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680201125X/ya6104Isup2.hkl |
CCDC reference: 193730
Data collection: SMART (Siemens 1996); cell refinement: SAINT (Bruker 1997b); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C26H30N2O | Dx = 1.246 Mg m−3 |
Mr = 386.52 | Melting point = 451–453 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.120 (1) Å | Cell parameters from 3250 reflections |
b = 8.950 (1) Å | θ = 2.2–24.7° |
c = 37.622 (4) Å | µ = 0.08 mm−1 |
V = 2060.7 (5) Å3 | T = 133 K |
Z = 4 | Block, colourless |
F(000) = 832 | 0.3 × 0.2 × 0.2 mm |
Locally modified Stoe-Siemens-Huber four-circles diffractometer | 1939 independent reflections |
Radiation source: fine-focus sealed tube | 1669 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 0 pixels mm-1 | θmax = 24.7°, θmin = 2.2° |
φ and ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | k = 0→10 |
Tmin = 0.978, Tmax = 0.985 | l = 0→43 |
23229 measured reflections |
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) = 0.092 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.5351P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1939 reflections | Δρmax = 0.13 e Å−3 |
264 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Absolute structure: Flack (1983); Friedel pairs were merged due to the lack of anomalous scatterers |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1 (3) |
Experimental. intnesities were measured with a SIEMENS CCD area-detector |
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. The hydrogen atoms were included in calculated positions and refined using a riding model. |
x | y | z | Uiso*/Ueq | ||
O | 0.0061 (4) | −0.5755 (2) | −0.06171 (4) | 0.0400 (5) | |
N1 | 0.1372 (4) | −0.1795 (2) | 0.23953 (5) | 0.0379 (6) | |
C1 | 0.2376 (5) | −0.3910 (3) | 0.01525 (7) | 0.0359 (7) | |
H1 | 0.3548 | −0.3242 | 0.0199 | 0.043* | |
C1' | 0.2936 (5) | −0.1872 (3) | 0.26636 (7) | 0.0348 (7) | |
N2 | 0.2147 (4) | −0.1367 (2) | 0.20503 (6) | 0.0372 (6) | |
C2 | 0.2025 (5) | −0.4380 (3) | −0.01926 (7) | 0.0384 (7) | |
H2 | 0.2949 | −0.4038 | −0.0378 | 0.046* | |
C2' | 0.4724 (5) | −0.0914 (3) | 0.26608 (7) | 0.0389 (7) | |
H2' | 0.4921 | −0.0239 | 0.2469 | 0.047* | |
C3 | 0.0318 (5) | −0.5355 (3) | −0.02674 (7) | 0.0349 (7) | |
C3' | 0.6211 (6) | −0.0938 (4) | 0.29356 (7) | 0.0476 (8) | |
H3' | 0.7416 | −0.0269 | 0.2933 | 0.057* | |
C4 | −0.1009 (5) | −0.5840 (3) | 0.00060 (7) | 0.0385 (7) | |
H4 | −0.2186 | −0.6500 | −0.0043 | 0.046* | |
C4' | 0.5972 (5) | −0.1927 (4) | 0.32168 (7) | 0.0465 (8) | |
H4' | 0.7019 | −0.1953 | 0.3403 | 0.056* | |
C5 | −0.0633 (5) | −0.5362 (3) | 0.03582 (7) | 0.0364 (7) | |
C5' | 0.4206 (6) | −0.2867 (3) | 0.32223 (8) | 0.0458 (8) | |
H5' | 0.4025 | −0.3539 | 0.3415 | 0.055* | |
C6 | −0.2191 (6) | −0.5950 (3) | 0.06378 (7) | 0.0460 (8) | |
H6A | −0.2337 | −0.7045 | 0.0609 | 0.055* | |
H6B | −0.3649 | −0.5500 | 0.0599 | 0.055* | |
C6' | 0.2672 (6) | −0.2850 (3) | 0.29488 (7) | 0.0403 (7) | |
H6' | 0.1450 | −0.3504 | 0.2957 | 0.048* | |
C7 | −0.1462 (6) | −0.5618 (3) | 0.10172 (7) | 0.0416 (8) | |
H7A | −0.2707 | −0.5754 | 0.1182 | 0.050* | |
H7B | −0.0290 | −0.6321 | 0.1087 | 0.050* | |
C8 | −0.0625 (5) | −0.4022 (3) | 0.10416 (7) | 0.0329 (7) | |
H8 | −0.1757 | −0.3341 | 0.0939 | 0.039* | |
C9 | 0.1472 (5) | −0.3875 (3) | 0.08187 (7) | 0.0309 (7) | |
H9 | 0.2555 | −0.4589 | 0.0923 | 0.037* | |
C10 | 0.1070 (5) | −0.4381 (3) | 0.04355 (7) | 0.0317 (7) | |
C11 | 0.2501 (5) | −0.2307 (3) | 0.08453 (6) | 0.0329 (7) | |
H11A | 0.1577 | −0.1590 | 0.0713 | 0.039* | |
H11B | 0.3956 | −0.2325 | 0.0730 | 0.039* | |
C12 | 0.2763 (5) | −0.1752 (3) | 0.12311 (6) | 0.0338 (7) | |
H12A | 0.3888 | −0.2359 | 0.1353 | 0.041* | |
H12B | 0.3264 | −0.0700 | 0.1229 | 0.041* | |
C13 | 0.0623 (5) | −0.1861 (3) | 0.14338 (7) | 0.0331 (7) | |
C14 | −0.0145 (5) | −0.3523 (3) | 0.14183 (7) | 0.0314 (7) | |
H14 | 0.1131 | −0.4133 | 0.1499 | 0.038* | |
C15 | −0.1902 (5) | −0.3701 (3) | 0.17088 (7) | 0.0355 (7) | |
H15A | −0.1857 | −0.4716 | 0.1813 | 0.043* | |
H15B | −0.3380 | −0.3520 | 0.1611 | 0.043* | |
C16 | −0.1316 (5) | −0.2510 (3) | 0.19906 (7) | 0.0389 (7) | |
H16 | −0.2552 | −0.1790 | 0.2020 | 0.047* | |
C16A | −0.0369 (5) | −0.2924 (3) | 0.23511 (7) | 0.0371 (7) | |
H16A | −0.1482 | −0.2843 | 0.2541 | 0.044* | |
H16B | 0.0237 | −0.3950 | 0.2350 | 0.044* | |
C17 | 0.0650 (5) | −0.1723 (3) | 0.18332 (7) | 0.0355 (7) | |
C18 | −0.1070 (5) | −0.0766 (3) | 0.12888 (7) | 0.0427 (8) | |
H18A | −0.0566 | 0.0260 | 0.1329 | 0.064* | |
H18B | −0.2465 | −0.0919 | 0.1411 | 0.064* | |
H18C | −0.1264 | −0.0935 | 0.1033 | 0.064* | |
C19 | −0.1755 (6) | −0.6699 (3) | −0.06984 (8) | 0.0459 (9) | |
H19A | −0.3116 | −0.6194 | −0.0632 | 0.069* | |
H19B | −0.1626 | −0.7636 | −0.0565 | 0.069* | |
H19C | −0.1769 | −0.6916 | −0.0954 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O | 0.0492 (14) | 0.0333 (10) | 0.0376 (10) | 0.0016 (11) | −0.0036 (10) | −0.0042 (9) |
N1 | 0.0433 (16) | 0.0369 (12) | 0.0335 (12) | −0.0074 (13) | 0.0108 (12) | −0.0024 (10) |
C1 | 0.0304 (17) | 0.0346 (14) | 0.0428 (15) | −0.0052 (15) | 0.0014 (14) | 0.0016 (12) |
C1' | 0.041 (2) | 0.0317 (14) | 0.0319 (14) | −0.0019 (15) | 0.0124 (14) | −0.0100 (12) |
N2 | 0.0441 (17) | 0.0315 (12) | 0.0362 (12) | −0.0047 (12) | 0.0096 (13) | −0.0021 (10) |
C2 | 0.037 (2) | 0.0389 (15) | 0.0393 (15) | 0.0008 (16) | 0.0040 (14) | 0.0018 (13) |
C2' | 0.0415 (19) | 0.0409 (15) | 0.0344 (14) | −0.0075 (16) | 0.0149 (15) | −0.0057 (13) |
C3 | 0.0400 (19) | 0.0283 (13) | 0.0363 (15) | 0.0091 (15) | 0.0020 (14) | 0.0008 (12) |
C3' | 0.041 (2) | 0.0625 (19) | 0.0390 (16) | −0.0132 (18) | 0.0128 (16) | −0.0093 (15) |
C4 | 0.0400 (19) | 0.0277 (13) | 0.0480 (16) | −0.0063 (15) | −0.0068 (15) | −0.0027 (12) |
C4' | 0.039 (2) | 0.063 (2) | 0.0374 (15) | −0.0033 (19) | 0.0044 (15) | −0.0028 (16) |
C5 | 0.038 (2) | 0.0294 (13) | 0.0415 (15) | −0.0034 (15) | 0.0015 (14) | 0.0035 (12) |
C5' | 0.055 (2) | 0.0425 (16) | 0.0394 (16) | −0.0010 (18) | 0.0033 (17) | 0.0047 (13) |
C6 | 0.046 (2) | 0.0447 (17) | 0.0479 (16) | −0.0188 (17) | 0.0091 (16) | −0.0040 (14) |
C6' | 0.044 (2) | 0.0323 (14) | 0.0443 (16) | −0.0052 (15) | 0.0094 (16) | −0.0026 (12) |
C7 | 0.044 (2) | 0.0359 (15) | 0.0445 (16) | −0.0121 (16) | 0.0059 (15) | 0.0031 (13) |
C8 | 0.0294 (18) | 0.0331 (14) | 0.0360 (14) | −0.0008 (14) | 0.0022 (13) | 0.0058 (12) |
C9 | 0.0232 (16) | 0.0305 (14) | 0.0391 (14) | −0.0025 (13) | 0.0015 (13) | 0.0039 (12) |
C10 | 0.0288 (17) | 0.0267 (13) | 0.0397 (14) | 0.0007 (14) | −0.0001 (14) | 0.0026 (11) |
C11 | 0.0273 (17) | 0.0359 (14) | 0.0356 (13) | −0.0056 (14) | −0.0001 (14) | 0.0040 (12) |
C12 | 0.0278 (18) | 0.0339 (14) | 0.0396 (14) | −0.0059 (14) | −0.0032 (13) | 0.0019 (12) |
C13 | 0.0306 (19) | 0.0303 (13) | 0.0385 (15) | −0.0017 (14) | 0.0025 (13) | 0.0033 (12) |
C14 | 0.0270 (18) | 0.0275 (13) | 0.0396 (14) | −0.0004 (14) | 0.0010 (13) | 0.0052 (12) |
C15 | 0.0288 (18) | 0.0356 (15) | 0.0420 (15) | −0.0003 (13) | 0.0046 (14) | 0.0040 (12) |
C16 | 0.0330 (18) | 0.0372 (15) | 0.0467 (16) | 0.0013 (15) | 0.0125 (15) | −0.0017 (13) |
C16A | 0.0358 (18) | 0.0348 (14) | 0.0406 (15) | −0.0051 (14) | 0.0119 (14) | −0.0040 (13) |
C17 | 0.039 (2) | 0.0270 (13) | 0.0400 (15) | −0.0007 (15) | 0.0034 (15) | 0.0006 (12) |
C18 | 0.043 (2) | 0.0350 (14) | 0.0504 (17) | 0.0031 (16) | 0.0023 (16) | 0.0049 (13) |
C19 | 0.056 (2) | 0.0346 (15) | 0.0471 (16) | 0.0048 (17) | −0.0088 (16) | −0.0064 (13) |
O—C3 | 1.373 (3) | C5—C6 | 1.514 (4) |
O—C19 | 1.430 (4) | C5'—C6' | 1.393 (4) |
N1—C1' | 1.393 (3) | C6—C7 | 1.525 (4) |
N1—N2 | 1.434 (3) | C7—C8 | 1.521 (4) |
N1—C16A | 1.478 (3) | C8—C14 | 1.514 (4) |
C1—C2 | 1.382 (4) | C8—C9 | 1.539 (4) |
C1—C10 | 1.397 (4) | C9—C10 | 1.531 (4) |
C1'—C2' | 1.390 (4) | C9—C11 | 1.542 (4) |
C1'—C6' | 1.395 (4) | C11—C12 | 1.543 (3) |
N2—C17 | 1.268 (4) | C12—C13 | 1.519 (4) |
C2—C3 | 1.390 (4) | C13—C17 | 1.508 (4) |
C2'—C3' | 1.378 (4) | C13—C18 | 1.527 (4) |
C3—C4 | 1.381 (4) | C13—C14 | 1.562 (4) |
C3'—C4' | 1.387 (4) | C14—C15 | 1.542 (4) |
C4—C5 | 1.411 (4) | C15—C16 | 1.546 (4) |
C4'—C5' | 1.369 (4) | C16—C17 | 1.514 (4) |
C5—C10 | 1.393 (4) | C16—C16A | 1.521 (4) |
C3—O—C19 | 116.7 (2) | C7—C8—C9 | 109.2 (2) |
C1'—N1—N2 | 116.2 (2) | C10—C9—C8 | 110.7 (2) |
C1'—N1—C16A | 122.9 (2) | C10—C9—C11 | 113.3 (2) |
N2—N1—C16A | 108.6 (2) | C8—C9—C11 | 112.5 (2) |
C2—C1—C10 | 122.4 (3) | C5—C10—C1 | 117.3 (2) |
C2'—C1'—N1 | 120.3 (2) | C5—C10—C9 | 120.2 (2) |
C2'—C1'—C6' | 119.0 (3) | C1—C10—C9 | 122.5 (2) |
N1—C1'—C6' | 120.6 (3) | C9—C11—C12 | 113.4 (2) |
C17—N2—N1 | 106.1 (2) | C13—C12—C11 | 111.2 (2) |
C1—C2—C3 | 119.9 (3) | C17—C13—C12 | 119.1 (2) |
C3'—C2'—C1' | 120.3 (3) | C17—C13—C18 | 108.1 (2) |
O—C3—C4 | 124.4 (3) | C12—C13—C18 | 111.4 (2) |
O—C3—C2 | 116.4 (2) | C17—C13—C14 | 96.8 (2) |
C4—C3—C2 | 119.3 (2) | C12—C13—C14 | 107.6 (2) |
C2'—C3'—C4' | 120.9 (3) | C18—C13—C14 | 113.2 (2) |
C3—C4—C5 | 120.5 (3) | C8—C14—C15 | 119.8 (2) |
C5'—C4'—C3' | 119.1 (3) | C8—C14—C13 | 112.0 (2) |
C10—C5—C4 | 120.6 (3) | C15—C14—C13 | 106.4 (2) |
C10—C5—C6 | 123.0 (2) | C14—C15—C16 | 104.7 (2) |
C4—C5—C6 | 116.4 (3) | C17—C16—C16A | 99.2 (2) |
C4'—C5'—C6' | 120.9 (3) | C17—C16—C15 | 103.7 (2) |
C5—C6—C7 | 113.5 (3) | C16A—C16—C15 | 122.2 (2) |
C5'—C6'—C1' | 119.8 (3) | N1—C16A—C16 | 102.0 (2) |
C8—C7—C6 | 109.8 (2) | N2—C17—C13 | 132.1 (3) |
C14—C8—C7 | 113.5 (2) | N2—C17—C16 | 116.1 (2) |
C14—C8—C9 | 108.8 (2) | C13—C17—C16 | 110.1 (2) |