research papers
In recent years, a series of non-linear optically active bis(benzylidene) ketones have been synthesized and investigated by electron crystallography. In most cases, structure refinement was possible by combining electron diffraction analysis and quantum-mechanical calculations with maximum-entropy methods. However, when the torsional angles between the phenyl rings and the C=C double bonds are strongly affected by the crystal field, this method fails because packing-energy calculations are not sufficiently sensitive. This problem can be solved by refining the approximate model with SHELXL, if the data set is sufficiently accurate and the model close to the correct structure. Here it is shown that a considerably superior data set can be obtained at 300 kV with on-line data acquisition.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108767300006668/au0194sup1.cif |
CCDC reference: 153322
Computing details top
(sim) top
Crystal data top
C22H22O5 | β = 91.710 (7)° |
Mr = 366.40 | V = 1861.9 (3) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 15.95 (2) Å | Dx = 1.307 Mg m−3 |
b = 13.87 (5) Å | Cu radiation, λ = 1.54178 Å |
c = 8.42 (1) Å | × × mm |
Crystal data top
C22H22O5 | β = 91.710 (7)° |
Mr = 366.40 | V = 1861.9 (3) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 15.95 (2) Å | Cu radiation, λ = 1.54178 Å |
b = 13.87 (5) Å | × × mm |
c = 8.42 (1) Å |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Biso*/Beq | ||
C1 | 0.5561 | 0.4578 | −0.2412 | ||
C2 | 0.4866 | 0.5028 | −0.3135 | ||
C3 | 0.4058 | 0.4826 | −0.2604 | ||
C4 | 0.3911 | 0.4159 | −0.1360 | ||
C5 | 0.4625 | 0.3715 | −0.0620 | ||
C6 | 0.5432 | 0.3923 | −0.1136 | ||
C7 | 0.3044 | 0.3995 | −0.0912 | ||
C8 | 0.2612 | 0.3177 | −0.0515 | ||
C9 | 0.1713 | 0.3335 | −0.0057 | ||
C10 | 0.1216 | 0.2483 | 0.0521 | ||
C11 | 0.1606 | 0.1488 | 0.0490 | ||
C12 | 0.2273 | 0.1401 | −0.0790 | ||
C13 | 0.2962 | 0.2161 | −0.0546 | ||
C14 | 0.0419 | 0.2688 | 0.1005 | ||
C15 | −0.0233 | 0.2081 | 0.1671 | ||
C16 | −0.0918 | 0.2557 | 0.2407 | ||
C17 | −0.1583 | 0.2051 | 0.3082 | ||
C18 | −0.1570 | 0.1022 | 0.3063 | ||
C19 | −0.0889 | 0.0546 | 0.2377 | ||
C20 | −0.0230 | 0.1060 | 0.1686 | ||
O21 | 0.6353 | 0.4764 | −0.2892 | ||
O22 | 0.6169 | 0.3554 | −0.0519 | ||
C23 | 0.6132 | 0.2900 | 0.0771 | ||
O24 | 0.1395 | 0.4150 | −0.0116 | ||
O25 | −0.2225 | 0.0558 | 0.3739 | ||
O26 | −0.2259 | 0.2456 | 0.3785 | ||
C27 | −0.2308 | 0.3474 | 0.3854 |
Geometric parameters (Å, º) top
C1—C2 | 1.402 | C10—C14 | 1.371 |
C1—C6 | 1.425 | C11—C12 | 1.534 |
C1—O21 | 1.357 | C12—C13 | 1.534 |
C2—C3 | 1.400 | C14—C15 | 1.460 |
C3—C4 | 1.421 | C15—C16 | 1.428 |
C4—C5 | 1.428 | C15—C20 | 1.417 |
C4—C7 | 1.458 | C16—C17 | 1.400 |
C5—C6 | 1.397 | C17—C18 | 1.428 |
C6—O22 | 1.375 | C17—O26 | 1.361 |
C7—C8 | 1.373 | C18—C19 | 1.404 |
C8—C9 | 1.508 | C18—O25 | 1.361 |
C8—C13 | 1.516 | C19—C20 | 1.404 |
C9—C10 | 1.509 | O22—C23 | 1.418 |
C9—O24 | 1.240 | O26—C27 | 1.416 |
C10—C11 | 1.515 | ||
C6—C1—C2 | 119.2 | C14—C10—C9 | 115.4 |
O21—C1—C2 | 121.3 | C14—C10—C11 | 125.2 |
O21—C1—C6 | 119.6 | C12—C11—C10 | 111.9 |
C3—C2—C1 | 119.9 | C13—C12—C11 | 110.9 |
C4—C3—C2 | 122.0 | C12—C13—C8 | 112.2 |
C5—C4—C3 | 117.5 | C15—C14—C10 | 131.8 |
C7—C4—C3 | 117.5 | C16—C15—C14 | 117.2 |
C7—C4—C5 | 125.0 | C20—C15—C14 | 125.3 |
C6—C5—C4 | 120.5 | C20—C15—C16 | 117.5 |
C5—C6—C1 | 120.9 | C17—C16—C15 | 122.3 |
O22—C6—C1 | 112.9 | C18—C17—C16 | 119.0 |
O22—C6—C5 | 126.3 | O26—C17—C16 | 125.6 |
C8—C7—C4 | 132.4 | O26—C17—C18 | 115.5 |
C9—C8—C7 | 115.2 | C19—C18—C17 | 119.1 |
C13—C8—C7 | 125.3 | O25—C18—C17 | 117.2 |
C13—C8—C9 | 119.5 | O25—C18—C19 | 123.7 |
C10—C9—C8 | 118.4 | C20—C19—C18 | 121.5 |
O24—C9—C8 | 120.8 | C19—C20—C15 | 120.5 |
O24—C9—C10 | 120.7 | C23—O22—C6 | 118.8 |
C11—C10—C9 | 119.4 | C27—O26—C17 | 118.3 |
(Xray) top
Crystal data top
C22H22O5 | β = 91.710 (7)° |
Mr = 366.40 | V = 1824.5 (3) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 15.937 (2) Å | Dx = 1.334 Mg m−3 |
b = 13.819 (1) Å | Cu radiation, λ = 1.54178 Å |
c = 8.288 (1) Å | × × mm |
Crystal data top
C22H22O5 | β = 91.710 (7)° |
Mr = 366.40 | V = 1824.5 (3) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 15.937 (2) Å | Cu radiation, λ = 1.54178 Å |
b = 13.819 (1) Å | × × mm |
c = 8.288 (1) Å |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Biso*/Beq | ||
C1 | 0.5674 (2) | 0.4447 (2) | −0.1976 (3) | ||
C2 | 0.5049 (2) | 0.4922 (2) | −0.2844 (3) | ||
C3 | 0.4216 (2) | 0.4723 (2) | −0.2558 (3) | ||
C4 | 0.3995 (2) | 0.4015 (2) | −0.1435 (3) | ||
C5 | 0.4637 (2) | 0.3537 (2) | −0.0563 (3) | ||
C6 | 0.5462 (2) | 0.3759 (2) | −0.0830 (3) | ||
C7 | 0.3102 (6) | 0.3873 (2) | −0.1140 (3) | ||
C8 | 0.2686 (2) | 0.3089 (2) | −0.0627 (3) | ||
C9 | 0.1778 (2) | 0.3216 (2) | −0.0315 (3) | ||
C10 | 0.1274 (2) | 0.2384 (2) | 0.0226 (3) | ||
C11 | 0.1636 (2) | 0.1377 (2) | 0.0108 (3) | ||
C12 | 0.2412 (2) | 0.1324 (2) | −0.0924 (4) | ||
C13 | 0.3054 (2) | 0.2093 (2) | −0.0408 (4) | ||
C14 | 0.0526 (2) | 0.2613 (2) | 0.0849 (3) | ||
C15 | −0.0107 (2) | 0.2047 (2) | 0.1661 (3) | ||
C16 | −0.0795 (2) | 0.2572 (2) | 0.2228 (3) | ||
C17 | −0.1409 (2) | 0.2131 (2) | 0.3114 (3) | ||
C18 | −0.1352 (2) | 0.1142 (2) | 0.3450 (3) | ||
C19 | −0.0687 (2) | 0.0617 (2) | 0.2876 (4) | ||
C20 | −0.0064 (2) | 0.1057 (2) | 0.2000 (4) | ||
O21 | 0.6488 (1) | 0.4654 (2) | −0.2271 (3) | ||
O22 | 0.6149 (1) | 0.3368 (2) | −0.0032 (3) | ||
C23 | 0.6018 (2) | 0.2641 (3) | 0.1120 (5) | ||
O24 | 0.1454 (1) | 0.4035 (1) | −0.0438 (3) | ||
O25 | −0.1958 (1) | 0.0742 (2) | 0.4360 (3) | ||
O26 | −0.2087 (1) | 0.2594 (2) | 0.3738 (8) | ||
C27 | −0.2087 (2) | 0.3620 (3) | 0.3710 (5) |
Geometric parameters (Å, º) top
C1—C2 | 1.378 (4) | C10—C14 | 1.351 (4) |
C1—C6 | 1.391 (4) | C11—C12 | 1.526 (4) |
C1—O21 | 1.357 (3) | C12—C13 | 1.529 (4) |
C2—C3 | 1.384 (4) | C14—C15 | 1.457 (4) |
C3—C4 | 1.402 (4) | C15—C16 | 1.407 (4) |
C4—C5 | 1.401 (4) | C15—C20 | 1.398 (4) |
C4—C7 | 1.465 (4) | C16—C17 | 1.382 (4) |
C5—C6 | 1.379 (4) | C17—C18 | 1.397 (4) |
C6—O22 | 1.370 (3) | C17—O26 | 1.370 (3) |
C7—C8 | 1.346 (4) | C18—C19 | 1.380 (4) |
C8—C9 | 1.487 (4) | C18—O25 | 1.361 (3) |
C8—C13 | 1.505 (4) | C19—C20 | 1.388 (4) |
C9—C10 | 1.480 (4) | O22—C23 | 1.406 (5) |
C9—O24 | 1.247 (3) | O26—C27 | 1.418 (4) |
C10—C11 | 1.511 (4) | ||
C6—C1—C2 | 119.9 (2) | C14—C10—C9 | 115.3 (2) |
O21—C1—C2 | 119.0 (2) | C14—C10—C11 | 125.7 (2) |
O21—C1—C6 | 121.1 (2) | C12—C11—C10 | 113.4 (2) |
C3—C2—C1 | 119.8 (2) | C13—C12—C11 | 110.9 (2) |
C4—C3—C2 | 121.0 (2) | C12—C13—C8 | 110.3 (2) |
C5—C4—C3 | 118.5 (2) | C15—C14—C10 | 133.0 (2) |
C7—C4—C3 | 118.0 (2) | C16—C15—C14 | 115.8 (2) |
C7—C4—C5 | 123.3 (2) | C20—C15—C14 | 125.9 (2) |
C6—C5—C4 | 119.9 (2) | C20—C15—C16 | 118.1 (2) |
C5—C6—C1 | 120.8 (2) | C17—C16—C15 | 121.4 (2) |
O22—C6—C1 | 113.3 (2) | C18—C17—C16 | 119.6 (2) |
O22—C6—C5 | 125.9 (2) | O26—C17—C16 | 125.0 (2) |
C8—C7—C4 | 130.7 (2) | O26—C17—C18 | 115.4 (2) |
C9—C8—C7 | 116.8 (2) | C19—C18—C17 | 119.4 (2) |
C13—C8—C7 | 125.4 (2) | O25—C18—C17 | 117.7 (2) |
C13—C8—C9 | 117.7 (2) | O25—C18—C19 | 122.9 (2) |
C10—C9—C8 | 120.1 (2) | C20—C19—C18 | 121.3 (2) |
O24—C9—C8 | 119.7 (2) | C19—C20—C15 | 120.1 (2) |
O24—C9—C10 | 120.2 (2) | C23—O22—C6 | 118.5 (2) |
C11—C10—C9 | 119.0 (2) | C27—O26—C17 | 117.5 (2) |
(em) top
Crystal data top
C22H22O5 | β = 91.710 (7)° |
Mr = 366.40 | V = 1824.5 (3) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 15.937 (2) Å | Dx = 1.334 Mg m−3 |
b = 13.819 (1) Å | Cu radiation, λ = 1.54178 Å |
c = 8.288 (1) Å | × × mm |
Crystal data top
C22H22O5 | β = 91.710 (7)° |
Mr = 366.40 | V = 1824.5 (3) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 15.937 (2) Å | Cu radiation, λ = 1.54178 Å |
b = 13.819 (1) Å | × × mm |
c = 8.288 (1) Å |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Biso*/Beq | ||
C1 | 0.570 (1) | 0.440 (2) | −0.198 (2) | ||
C2 | 0.508 (2) | 0.491 (1) | −0.282 (1) | ||
C3 | 0.424 (2) | 0.473 (1) | −0.252 (2) | ||
C4 | 0.402 (1) | 0.405 (2) | −0.138 (2) | ||
C5 | 0.465 (2) | 0.354 (1) | −0.053 (2) | ||
C6 | 0.549 (2) | 0.372 (1) | −0.083 (2) | ||
C7 | 0.312 (3) | 0.380 (2) | −0.120 (3) | ||
C8 | 0.270 (3) | 0.316 (2) | −0.066 (3) | ||
C9 | 0.182 (3) | 0.325 (2) | −0.031 (3) | ||
C10 | 0.120 (3) | 0.238 (2) | 0.022 (3) | ||
C11 | 0.164 (2) | 0.140 (1) | 0.023 (3) | ||
C12 | 0.233 (2) | 0.129 (2) | −0.091 (3) | ||
C13 | 0.304 (2) | 0.210 (1) | −0.040 (3) | ||
C14 | 0.055 (3) | 0.262 (2) | 0.091 (3) | ||
C15 | −0.019 (1) | 0.205 (1) | 0.163 (2) | ||
C16 | −0.084 (1) | 0.260 (1) | 0.225 (2) | ||
C17 | −0.143 (1) | 0.215 (1) | 0.321 (2) | ||
C18 | −0.137 (1) | 0.117 (2) | 0.355 (2) | ||
C19 | −0.072 (2) | 0.063 (1) | 0.292 (2) | ||
C20 | −0.013 (1) | 0.107 (1) | 0.196 (2) | ||
O21 | 0.637 (2) | 0.469 (1) | −0.234 (2) | ||
O22 | 0.614 (2) | 0.342 (1) | −0.011 (3) | ||
C23 | 0.602 (2) | 0.269 (2) | 0.110 (2) | ||
O24 | 0.142 (2) | 0.413 (2) | −0.042 (3) | ||
O25 | −0.194 (2) | 0.068 (2) | 0.428 (2) | ||
O26 | −0.212 (3) | 0.259 (2) | 0.367 (3) | ||
C27 | −0.208 (2) | 0.358 (1) | 0.372 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.39 (3) | C10—C14 | 1.25 (6) |
C1—C6 | 1.39 (3) | C11—C12 | 1.48 (5) |
C1—O21 | 1.19 (4) | C12—C13 | 1.64 (4) |
C2—C3 | 1.39 (4) | C14—C15 | 1.55 (4) |
C3—C4 | 1.39 (3) | C15—C16 | 1.39 (3) |
C4—C5 | 1.39 (3) | C15—C20 | 1.39 (3) |
C4—C7 | 1.50 (5) | C16—C17 | 1.39 (3) |
C5—C6 | 1.39 (4) | C17—C18 | 1.39 (3) |
C6—O22 | 1.26 (4) | C17—O26 | 1.32 (4) |
C7—C8 | 1.20 (5) | C18—C19 | 1.39 (3) |
C8—C9 | 1.45 (7) | C18—O25 | 1.30 (3) |
C8—C13 | 1.57 (4) | C19—C20 | 1.39 (3) |
C9—C10 | 1.62 (5) | O22—C23 | 1.44 (3) |
C9—O24 | 1.37 (5) | O26—C27 | 1.36 (3) |
C10—C11 | 1.53 (4) | ||
C6—C1—C2 | 120 (2) | C14—C10—C9 | 116 (3) |
O21—C1—C2 | 110 (2) | C14—C10—C11 | 129 (3) |
O21—C1—C6 | 130 (2) | C12—C11—C10 | 115 (2) |
C3—C2—C1 | 120 (2) | C13—C12—C11 | 107 (2) |
C4—C3—C2 | 120 (2) | C12—C13—C8 | 111 (2) |
C5—C4—C3 | 120 (2) | C15—C14—C10 | 134 (3) |
C7—C4—C3 | 119 (2) | C16—C15—C14 | 117 (2) |
C7—C4—C5 | 121 (2) | C20—C15—C14 | 122 (2) |
C6—C5—C4 | 120 (2) | C20—C15—C16 | 120 (1) |
C5—C6—C1 | 120 (2) | C17—C16—C15 | 120 (1) |
O22—C6—C1 | 110 (2) | C18—C17—C16 | 120 (2) |
O22—C6—C5 | 130 (2) | O26—C17—C16 | 123 (2) |
C8—C7—C4 | 139 (3) | O26—C17—C18 | 116 (2) |
C9—C8—C7 | 124 (3) | C19—C18—C17 | 120 (2) |
C13—C8—C7 | 123 (3) | O25—C18—C17 | 124 (2) |
C13—C8—C9 | 113 (3) | O25—C18—C19 | 116 (2) |
C10—C9—C8 | 126 (3) | C20—C19—C18 | 120 (2) |
O24—C9—C8 | 121 (3) | C19—C20—C15 | 120 (1) |
O24—C9—C10 | 113 (3) | C23—O22—C6 | 116 (2) |
C11—C10—C9 | 113 (3) | C27—O26—C17 | 115 (3) |
Experimental details
(sim) | (Xray) | (em) | |
Crystal data | |||
Chemical formula | C22H22O5 | C22H22O5 | C22H22O5 |
Mr | 366.40 | 366.40 | 366.40 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | ? | ? | ? |
a, b, c (Å) | 15.95 (2), 13.87 (5), 8.42 (1) | 15.937 (2), 13.819 (1), 8.288 (1) | 15.937 (2), 13.819 (1), 8.288 (1) |
β (°) | ?, 91.710 (7), ? | ?, 91.710 (7), ? | ?, 91.710 (7), ? |
V (Å3) | 1861.9 (3) | 1824.5 (3) | 1824.5 (3) |
Z | 4 | 4 | 4 |
Radiation type | Cu, λ = 1.54178 Å | Cu, λ = 1.54178 Å | Cu, λ = 1.54178 Å |
µ (mm−1) | ? | ? | ? |
Crystal size (mm) | × × | × × | × × |
Data collection | |||
Diffractometer | ? | ? | ? |
Absorption correction | ? | ? | ? |
No. of measured, independent and observed (?) reflections | ?, ?, ? | ?, ?, ? | ?, ?, ? |
Rint | ? | ? | ? |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | ?, ?, ? | ?, ?, ? | ?, ?, ? |
No. of reflections | ? | ? | ? |
No. of parameters | ? | ? | ? |
No. of restraints | ? | ? | ? |
Δρmax, Δρmin (e Å−3) | ?, ? | ?, ? | ?, ? |
Selected geometric parameters (Å, º) for (sim) top
C1—C2 | 1.402 | C10—C14 | 1.371 |
C1—C6 | 1.425 | C11—C12 | 1.534 |
C1—O21 | 1.357 | C12—C13 | 1.534 |
C2—C3 | 1.400 | C14—C15 | 1.460 |
C3—C4 | 1.421 | C15—C16 | 1.428 |
C4—C5 | 1.428 | C15—C20 | 1.417 |
C4—C7 | 1.458 | C16—C17 | 1.400 |
C5—C6 | 1.397 | C17—C18 | 1.428 |
C6—O22 | 1.375 | C17—O26 | 1.361 |
C7—C8 | 1.373 | C18—C19 | 1.404 |
C8—C9 | 1.508 | C18—O25 | 1.361 |
C8—C13 | 1.516 | C19—C20 | 1.404 |
C9—C10 | 1.509 | O22—C23 | 1.418 |
C9—O24 | 1.240 | O26—C27 | 1.416 |
C10—C11 | 1.515 | ||
C6—C1—C2 | 119.2 | C14—C10—C9 | 115.4 |
O21—C1—C2 | 121.3 | C14—C10—C11 | 125.2 |
O21—C1—C6 | 119.6 | C12—C11—C10 | 111.9 |
C3—C2—C1 | 119.9 | C13—C12—C11 | 110.9 |
C4—C3—C2 | 122.0 | C12—C13—C8 | 112.2 |
C5—C4—C3 | 117.5 | C15—C14—C10 | 131.8 |
C7—C4—C3 | 117.5 | C16—C15—C14 | 117.2 |
C7—C4—C5 | 125.0 | C20—C15—C14 | 125.3 |
C6—C5—C4 | 120.5 | C20—C15—C16 | 117.5 |
C5—C6—C1 | 120.9 | C17—C16—C15 | 122.3 |
O22—C6—C1 | 112.9 | C18—C17—C16 | 119.0 |
O22—C6—C5 | 126.3 | O26—C17—C16 | 125.6 |
C8—C7—C4 | 132.4 | O26—C17—C18 | 115.5 |
C9—C8—C7 | 115.2 | C19—C18—C17 | 119.1 |
C13—C8—C7 | 125.3 | O25—C18—C17 | 117.2 |
C13—C8—C9 | 119.5 | O25—C18—C19 | 123.7 |
C10—C9—C8 | 118.4 | C20—C19—C18 | 121.5 |
O24—C9—C8 | 120.8 | C19—C20—C15 | 120.5 |
O24—C9—C10 | 120.7 | C23—O22—C6 | 118.8 |
C11—C10—C9 | 119.4 | C27—O26—C17 | 118.3 |
Selected geometric parameters (Å, º) for (Xray) top
C1—C2 | 1.378 (4) | C10—C14 | 1.351 (4) |
C1—C6 | 1.391 (4) | C11—C12 | 1.526 (4) |
C1—O21 | 1.357 (3) | C12—C13 | 1.529 (4) |
C2—C3 | 1.384 (4) | C14—C15 | 1.457 (4) |
C3—C4 | 1.402 (4) | C15—C16 | 1.407 (4) |
C4—C5 | 1.401 (4) | C15—C20 | 1.398 (4) |
C4—C7 | 1.465 (4) | C16—C17 | 1.382 (4) |
C5—C6 | 1.379 (4) | C17—C18 | 1.397 (4) |
C6—O22 | 1.370 (3) | C17—O26 | 1.370 (3) |
C7—C8 | 1.346 (4) | C18—C19 | 1.380 (4) |
C8—C9 | 1.487 (4) | C18—O25 | 1.361 (3) |
C8—C13 | 1.505 (4) | C19—C20 | 1.388 (4) |
C9—C10 | 1.480 (4) | O22—C23 | 1.406 (5) |
C9—O24 | 1.247 (3) | O26—C27 | 1.418 (4) |
C10—C11 | 1.511 (4) | ||
C6—C1—C2 | 119.9 (2) | C14—C10—C9 | 115.3 (2) |
O21—C1—C2 | 119.0 (2) | C14—C10—C11 | 125.7 (2) |
O21—C1—C6 | 121.1 (2) | C12—C11—C10 | 113.4 (2) |
C3—C2—C1 | 119.8 (2) | C13—C12—C11 | 110.9 (2) |
C4—C3—C2 | 121.0 (2) | C12—C13—C8 | 110.3 (2) |
C5—C4—C3 | 118.5 (2) | C15—C14—C10 | 133.0 (2) |
C7—C4—C3 | 118.0 (2) | C16—C15—C14 | 115.8 (2) |
C7—C4—C5 | 123.3 (2) | C20—C15—C14 | 125.9 (2) |
C6—C5—C4 | 119.9 (2) | C20—C15—C16 | 118.1 (2) |
C5—C6—C1 | 120.8 (2) | C17—C16—C15 | 121.4 (2) |
O22—C6—C1 | 113.3 (2) | C18—C17—C16 | 119.6 (2) |
O22—C6—C5 | 125.9 (2) | O26—C17—C16 | 125.0 (2) |
C8—C7—C4 | 130.7 (2) | O26—C17—C18 | 115.4 (2) |
C9—C8—C7 | 116.8 (2) | C19—C18—C17 | 119.4 (2) |
C13—C8—C7 | 125.4 (2) | O25—C18—C17 | 117.7 (2) |
C13—C8—C9 | 117.7 (2) | O25—C18—C19 | 122.9 (2) |
C10—C9—C8 | 120.1 (2) | C20—C19—C18 | 121.3 (2) |
O24—C9—C8 | 119.7 (2) | C19—C20—C15 | 120.1 (2) |
O24—C9—C10 | 120.2 (2) | C23—O22—C6 | 118.5 (2) |
C11—C10—C9 | 119.0 (2) | C27—O26—C17 | 117.5 (2) |
Selected geometric parameters (Å, º) for (em) top
C1—C2 | 1.39 (3) | C10—C14 | 1.25 (6) |
C1—C6 | 1.39 (3) | C11—C12 | 1.48 (5) |
C1—O21 | 1.19 (4) | C12—C13 | 1.64 (4) |
C2—C3 | 1.39 (4) | C14—C15 | 1.55 (4) |
C3—C4 | 1.39 (3) | C15—C16 | 1.39 (3) |
C4—C5 | 1.39 (3) | C15—C20 | 1.39 (3) |
C4—C7 | 1.50 (5) | C16—C17 | 1.39 (3) |
C5—C6 | 1.39 (4) | C17—C18 | 1.39 (3) |
C6—O22 | 1.26 (4) | C17—O26 | 1.32 (4) |
C7—C8 | 1.20 (5) | C18—C19 | 1.39 (3) |
C8—C9 | 1.45 (7) | C18—O25 | 1.30 (3) |
C8—C13 | 1.57 (4) | C19—C20 | 1.39 (3) |
C9—C10 | 1.62 (5) | O22—C23 | 1.44 (3) |
C9—O24 | 1.37 (5) | O26—C27 | 1.36 (3) |
C10—C11 | 1.53 (4) | ||
C6—C1—C2 | 120 (2) | C14—C10—C9 | 116 (3) |
O21—C1—C2 | 110 (2) | C14—C10—C11 | 129 (3) |
O21—C1—C6 | 130 (2) | C12—C11—C10 | 115 (2) |
C3—C2—C1 | 120 (2) | C13—C12—C11 | 107 (2) |
C4—C3—C2 | 120 (2) | C12—C13—C8 | 111 (2) |
C5—C4—C3 | 120 (2) | C15—C14—C10 | 134 (3) |
C7—C4—C3 | 119 (2) | C16—C15—C14 | 117 (2) |
C7—C4—C5 | 121 (2) | C20—C15—C14 | 122 (2) |
C6—C5—C4 | 120 (2) | C20—C15—C16 | 120 (1) |
C5—C6—C1 | 120 (2) | C17—C16—C15 | 120 (1) |
O22—C6—C1 | 110 (2) | C18—C17—C16 | 120 (2) |
O22—C6—C5 | 130 (2) | O26—C17—C16 | 123 (2) |
C8—C7—C4 | 139 (3) | O26—C17—C18 | 116 (2) |
C9—C8—C7 | 124 (3) | C19—C18—C17 | 120 (2) |
C13—C8—C7 | 123 (3) | O25—C18—C17 | 124 (2) |
C13—C8—C9 | 113 (3) | O25—C18—C19 | 116 (2) |
C10—C9—C8 | 126 (3) | C20—C19—C18 | 120 (2) |
O24—C9—C8 | 121 (3) | C19—C20—C15 | 120 (1) |
O24—C9—C10 | 113 (3) | C23—O22—C6 | 116 (2) |
C11—C10—C9 | 113 (3) | C27—O26—C17 | 115 (3) |