Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101019163/fr1354sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101019163/fr1354Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101019163/fr1354IIsup3.hkl |
CCDC references: 180162; 180163
Calixarenes (I) and (II) were synthesized by reaction of calix[4]arene with the appropriate bromoalkyl acetate according to previously described procedures (Aoki et al., 1992). Calixarene (I) was recrystallized from a methanol/chloroform mixture. Crystals of (II) suitable for diffraction analysis were obtained by recrystallization from an ethyl acetate/chloroform mixture and immediately transferred to the diffractometer, as the crystals degraded, losing solvent, after standing for a short time in air.
All H atoms were included in idealized positions with X—H distances of 0.84, 0.95, 0.99 and 0.98 Å for hydroxyl, methine, methylene and methyl H, respectively. The coordinates of these fixed atoms were allowed to ride on those of the parent atoms. The displacement parameters of the H atoms were constrained to be a factor of 1.2 greater than those of the parent atoms for those associated with aromatic moities and 1.5 greater than the parent values for the others. A Flack (1983) parameter of -0.10 (4), determined by refinement using 3510 Friedel pairs, indicated that the correct absolute structure of (II) has been identified.
For both compounds, cell refinement: DENZO (Hooft 1998) and COLLECT (Otwinowski & Minor, 1997); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).
Fig. 1. View of (I) shown with 50% probability displacement ellipsoids. | |
Fig. 2. View of (II) shown with 50% probability displacement ellipsoids. | |
Fig. 3. The supramolecular structure exhibited by (I). |
C34H32O8 | F(000) = 5400 |
Mr = 568.6 | Dx = 1.307 Mg m−3 |
Rhombohedral, R3 | Mo Kα radiation, λ = 0.71073 Å |
a = 32.840 (5) Å | Cell parameters from 13396 reflections |
c = 13.918 (3) Å | θ = 1.0–30.5° |
α = 90° | µ = 0.09 mm−1 |
γ = 120° | T = 150 K |
V = 13000 (4) Å3 | Block, colourless |
Z = 18 | 0.3 × 0.2 × 0.2 mm |
Nonius KappaCCD area-detector diffractometer | 4617 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.044 |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | θmax = 27.5°, θmin = 2.2° |
Tmin = 0.973, Tmax = 0.982 | h = −42→33 |
25617 measured reflections | k = −30→42 |
6609 independent reflections | l = −17→18 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0542P)2 + 5.423P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.044 | (Δ/σ)max = 0.002 |
wR(F2) = 0.114 | Δρmax = 0.24 e Å−3 |
S = 1.04 | Δρmin = −0.20 e Å−3 |
6609 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
384 parameters | Extinction coefficient: 0.00040 (7) |
0 restraints |
C34H32O8 | V = 13000 (4) Å3 |
Mr = 568.6 | Z = 18 |
Rhombohedral, R3 | Mo Kα radiation |
a = 32.840 (5) Å | µ = 0.09 mm−1 |
c = 13.918 (3) Å | T = 150 K |
α = 90° | 0.3 × 0.2 × 0.2 mm |
γ = 120° |
Nonius KappaCCD area-detector diffractometer | 6609 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 4617 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.982 | Rint = 0.044 |
25617 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
6609 reflections | Δρmin = −0.20 e Å−3 |
384 parameters |
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 | 0.56335 (5) | 0.78110 (5) | 0.16352 (10) | 0.0320 (3) | |
H1A | 0.5298 | 0.7715 | 0.1715 | 0.038* | |
H1B | 0.5732 | 0.7948 | 0.0985 | 0.038* | |
C2 | 0.56859 (5) | 0.73802 (5) | 0.17118 (10) | 0.0311 (3) | |
C3 | 0.59427 (5) | 0.72950 (6) | 0.10245 (11) | 0.0375 (4) | |
H3 | 0.6084 | 0.7511 | 0.0509 | 0.045* | |
C4 | 0.59978 (5) | 0.69053 (6) | 0.10721 (12) | 0.0420 (4) | |
H4 | 0.6173 | 0.6853 | 0.0593 | 0.050* | |
C5 | 0.57964 (5) | 0.65926 (6) | 0.18224 (12) | 0.0396 (4) | |
H5 | 0.5835 | 0.6325 | 0.1857 | 0.048* | |
C6 | 0.55384 (5) | 0.66618 (5) | 0.25266 (11) | 0.0341 (4) | |
C7 | 0.54816 (5) | 0.70557 (5) | 0.24602 (10) | 0.0300 (3) | |
C8 | 0.53106 (6) | 0.63158 (5) | 0.33435 (12) | 0.0367 (4) | |
H8A | 0.4984 | 0.6251 | 0.3426 | 0.044* | |
H8B | 0.5296 | 0.6016 | 0.3171 | 0.044* | |
C9 | 0.55699 (5) | 0.64900 (5) | 0.42880 (11) | 0.0322 (3) | |
C10 | 0.59991 (6) | 0.65119 (5) | 0.44250 (13) | 0.0401 (4) | |
H10 | 0.6124 | 0.6410 | 0.3926 | 0.048* | |
C11 | 0.62482 (5) | 0.66790 (6) | 0.52713 (13) | 0.0426 (4) | |
H11 | 0.6534 | 0.6678 | 0.5363 | 0.051* | |
C12 | 0.60802 (5) | 0.68476 (6) | 0.59812 (12) | 0.0389 (4) | |
H12 | 0.6258 | 0.6974 | 0.6552 | 0.047* | |
C13 | 0.56553 (5) | 0.68366 (5) | 0.58774 (11) | 0.0319 (3) | |
C14 | 0.53999 (5) | 0.66399 (5) | 0.50432 (11) | 0.0295 (3) | |
C15 | 0.54940 (6) | 0.70594 (6) | 0.66286 (11) | 0.0373 (4) | |
H15A | 0.5152 | 0.6934 | 0.6560 | 0.045* | |
H15B | 0.5552 | 0.6975 | 0.7277 | 0.045* | |
C16 | 0.57482 (5) | 0.75888 (5) | 0.65322 (10) | 0.0329 (3) | |
C17 | 0.61101 (6) | 0.78698 (6) | 0.71592 (11) | 0.0426 (4) | |
H17 | 0.6198 | 0.7725 | 0.7646 | 0.051* | |
C18 | 0.63446 (6) | 0.83522 (6) | 0.70923 (12) | 0.0467 (4) | |
H18 | 0.6586 | 0.8538 | 0.7537 | 0.056* | |
C19 | 0.62265 (5) | 0.85650 (6) | 0.63738 (11) | 0.0378 (4) | |
H19 | 0.6388 | 0.8898 | 0.6331 | 0.045* | |
C20 | 0.58757 (5) | 0.82999 (5) | 0.57129 (10) | 0.0296 (3) | |
C21 | 0.56329 (5) | 0.78108 (5) | 0.58095 (10) | 0.0286 (3) | |
C22 | 0.57563 (5) | 0.85367 (5) | 0.49139 (10) | 0.0311 (3) | |
H22A | 0.5864 | 0.8866 | 0.5101 | 0.037* | |
H22B | 0.5410 | 0.8374 | 0.4837 | 0.037* | |
C23 | 0.59770 (5) | 0.85348 (5) | 0.39546 (10) | 0.0263 (3) | |
C24 | 0.64517 (5) | 0.88396 (5) | 0.37778 (10) | 0.0285 (3) | |
H24 | 0.6637 | 0.9064 | 0.4253 | 0.034* | |
C25 | 0.66603 (5) | 0.88238 (5) | 0.29275 (10) | 0.0291 (3) | |
H25 | 0.6983 | 0.9042 | 0.2816 | 0.035* | |
C26 | 0.63988 (5) | 0.84906 (5) | 0.22396 (10) | 0.0283 (3) | |
H26 | 0.6547 | 0.8471 | 0.1669 | 0.034* | |
C27 | 0.59210 (5) | 0.81839 (5) | 0.23756 (10) | 0.0266 (3) | |
C28 | 0.57179 (5) | 0.82241 (5) | 0.32210 (10) | 0.0252 (3) | |
C29 | 0.49624 (5) | 0.81350 (5) | 0.30570 (12) | 0.0321 (3) | |
H29A | 0.5073 | 0.8293 | 0.2428 | 0.039* | |
H29B | 0.4997 | 0.8373 | 0.3537 | 0.039* | |
C30 | 0.44584 (5) | 0.77557 (5) | 0.29865 (10) | 0.0265 (3) | |
C31 | 0.36809 (5) | 0.76153 (6) | 0.28930 (12) | 0.0428 (4) | |
H31A | 0.3619 | 0.7452 | 0.2275 | 0.064* | |
H31B | 0.3509 | 0.7787 | 0.2924 | 0.064* | |
H31C | 0.3577 | 0.7385 | 0.3416 | 0.064* | |
C32 | 0.45809 (5) | 0.61746 (5) | 0.52656 (13) | 0.0378 (4) | |
H32A | 0.4654 | 0.6084 | 0.5893 | 0.045* | |
H32B | 0.4521 | 0.5926 | 0.4792 | 0.045* | |
C33 | 0.41585 (5) | 0.62333 (5) | 0.53537 (10) | 0.0304 (3) | |
C34 | 0.33309 (5) | 0.58229 (7) | 0.54553 (13) | 0.0472 (4) | |
H34A | 0.3329 | 0.5970 | 0.6066 | 0.071* | |
H34B | 0.3065 | 0.5500 | 0.5437 | 0.071* | |
H34C | 0.3304 | 0.6003 | 0.4923 | 0.071* | |
O2 | 0.52051 (4) | 0.70860 (4) | 0.31499 (7) | 0.0357 (3) | |
H2 | 0.5191 | 0.7332 | 0.3067 | 0.054* | |
O1 | 0.49634 (3) | 0.66134 (3) | 0.49579 (7) | 0.0319 (3) | |
O3 | 0.52325 (3) | 0.79260 (3) | 0.33383 (7) | 0.0281 (2) | |
O4 | 0.52754 (4) | 0.75722 (4) | 0.51796 (8) | 0.0363 (3) | |
H4A | 0.5166 | 0.7282 | 0.5253 | 0.054* | |
O5 | 0.41717 (4) | 0.66008 (4) | 0.54139 (9) | 0.0470 (3) | |
O6 | 0.37676 (4) | 0.58146 (4) | 0.53655 (8) | 0.0402 (3) | |
O7 | 0.43258 (4) | 0.73475 (4) | 0.29201 (9) | 0.0451 (3) | |
O8 | 0.41804 (3) | 0.79429 (4) | 0.29878 (8) | 0.0367 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0305 (8) | 0.0292 (8) | 0.0334 (8) | 0.0127 (7) | −0.0068 (6) | 0.0002 (6) |
C2 | 0.0255 (8) | 0.0271 (8) | 0.0351 (8) | 0.0090 (7) | −0.0108 (6) | −0.0092 (6) |
C3 | 0.0253 (8) | 0.0359 (9) | 0.0412 (9) | 0.0077 (7) | −0.0078 (7) | −0.0103 (7) |
C4 | 0.0267 (8) | 0.0406 (10) | 0.0544 (10) | 0.0136 (8) | −0.0051 (7) | −0.0202 (8) |
C5 | 0.0278 (8) | 0.0293 (9) | 0.0608 (11) | 0.0135 (7) | −0.0118 (7) | −0.0178 (8) |
C6 | 0.0290 (8) | 0.0260 (8) | 0.0469 (9) | 0.0135 (7) | −0.0130 (7) | −0.0111 (7) |
C7 | 0.0282 (8) | 0.0258 (8) | 0.0359 (8) | 0.0134 (7) | −0.0093 (6) | −0.0091 (6) |
C8 | 0.0329 (9) | 0.0206 (8) | 0.0572 (10) | 0.0138 (7) | −0.0090 (7) | −0.0081 (7) |
C9 | 0.0259 (8) | 0.0182 (7) | 0.0527 (9) | 0.0111 (6) | −0.0046 (7) | 0.0009 (6) |
C10 | 0.0309 (9) | 0.0310 (9) | 0.0639 (11) | 0.0196 (7) | −0.0035 (8) | −0.0044 (8) |
C11 | 0.0235 (8) | 0.0340 (9) | 0.0718 (12) | 0.0155 (7) | −0.0069 (8) | 0.0020 (8) |
C12 | 0.0286 (9) | 0.0336 (9) | 0.0521 (10) | 0.0138 (7) | −0.0102 (7) | 0.0025 (7) |
C13 | 0.0265 (8) | 0.0254 (8) | 0.0424 (9) | 0.0118 (7) | 0.0003 (6) | 0.0091 (6) |
C14 | 0.0199 (7) | 0.0198 (7) | 0.0490 (9) | 0.0101 (6) | −0.0011 (6) | 0.0077 (6) |
C15 | 0.0367 (9) | 0.0393 (9) | 0.0348 (8) | 0.0183 (8) | 0.0024 (7) | 0.0104 (7) |
C16 | 0.0316 (8) | 0.0368 (9) | 0.0305 (8) | 0.0173 (7) | 0.0052 (6) | 0.0038 (6) |
C17 | 0.0473 (10) | 0.0492 (11) | 0.0308 (8) | 0.0237 (9) | −0.0035 (7) | 0.0026 (7) |
C18 | 0.0452 (10) | 0.0481 (11) | 0.0375 (9) | 0.0164 (9) | −0.0097 (8) | −0.0082 (8) |
C19 | 0.0340 (9) | 0.0339 (9) | 0.0392 (9) | 0.0121 (7) | 0.0009 (7) | −0.0063 (7) |
C20 | 0.0285 (8) | 0.0319 (8) | 0.0306 (7) | 0.0168 (7) | 0.0046 (6) | −0.0018 (6) |
C21 | 0.0245 (8) | 0.0306 (8) | 0.0300 (7) | 0.0131 (7) | 0.0029 (6) | −0.0021 (6) |
C22 | 0.0292 (8) | 0.0241 (8) | 0.0418 (9) | 0.0148 (7) | 0.0010 (6) | −0.0038 (6) |
C23 | 0.0245 (7) | 0.0211 (7) | 0.0367 (8) | 0.0140 (6) | −0.0023 (6) | 0.0017 (6) |
C24 | 0.0247 (8) | 0.0205 (7) | 0.0386 (8) | 0.0101 (6) | −0.0075 (6) | −0.0024 (6) |
C25 | 0.0203 (7) | 0.0235 (7) | 0.0416 (8) | 0.0094 (6) | −0.0026 (6) | 0.0045 (6) |
C26 | 0.0270 (8) | 0.0283 (8) | 0.0320 (8) | 0.0156 (7) | −0.0005 (6) | 0.0048 (6) |
C27 | 0.0270 (8) | 0.0220 (7) | 0.0327 (7) | 0.0138 (6) | −0.0065 (6) | 0.0030 (6) |
C28 | 0.0189 (7) | 0.0175 (7) | 0.0390 (8) | 0.0088 (6) | −0.0032 (6) | 0.0051 (6) |
C29 | 0.0233 (8) | 0.0236 (8) | 0.0506 (9) | 0.0127 (6) | −0.0035 (6) | 0.0076 (6) |
C30 | 0.0240 (7) | 0.0267 (8) | 0.0273 (7) | 0.0116 (6) | −0.0007 (6) | 0.0037 (6) |
C31 | 0.0203 (8) | 0.0534 (11) | 0.0504 (10) | 0.0152 (8) | −0.0034 (7) | 0.0028 (8) |
C32 | 0.0229 (8) | 0.0270 (8) | 0.0600 (10) | 0.0098 (7) | 0.0015 (7) | 0.0127 (7) |
C33 | 0.0251 (8) | 0.0340 (9) | 0.0298 (7) | 0.0131 (7) | −0.0002 (6) | 0.0053 (6) |
C34 | 0.0222 (8) | 0.0604 (12) | 0.0525 (10) | 0.0158 (8) | 0.0048 (7) | 0.0040 (9) |
O2 | 0.0453 (7) | 0.0253 (6) | 0.0426 (6) | 0.0221 (5) | 0.0027 (5) | 0.0029 (4) |
O1 | 0.0185 (5) | 0.0251 (5) | 0.0512 (6) | 0.0102 (4) | 0.0012 (4) | 0.0105 (4) |
O3 | 0.0185 (5) | 0.0205 (5) | 0.0441 (6) | 0.0088 (4) | −0.0038 (4) | 0.0056 (4) |
O4 | 0.0340 (6) | 0.0251 (6) | 0.0475 (6) | 0.0131 (5) | −0.0082 (5) | 0.0013 (5) |
O5 | 0.0359 (7) | 0.0363 (7) | 0.0718 (8) | 0.0204 (6) | 0.0098 (6) | 0.0041 (6) |
O6 | 0.0217 (6) | 0.0368 (6) | 0.0543 (7) | 0.0089 (5) | 0.0032 (5) | 0.0048 (5) |
O7 | 0.0308 (6) | 0.0250 (6) | 0.0738 (8) | 0.0098 (5) | −0.0114 (5) | −0.0039 (5) |
O8 | 0.0222 (5) | 0.0360 (6) | 0.0526 (7) | 0.0149 (5) | −0.0040 (5) | 0.0010 (5) |
C31—O8 | 1.4495 (18) | C12—H12 | 0.9500 |
C31—H31A | 0.9800 | C13—C14 | 1.388 (2) |
C31—H31B | 0.9800 | C13—C15 | 1.515 (2) |
C31—H31C | 0.9800 | C14—O1 | 1.3969 (17) |
C32—O1 | 1.4241 (17) | C15—C16 | 1.512 (2) |
C32—C33 | 1.498 (2) | C15—H15A | 0.9900 |
C32—H32A | 0.9900 | C15—H15B | 0.9900 |
C32—H32B | 0.9900 | C16—C17 | 1.389 (2) |
C33—O5 | 1.1889 (18) | C16—C21 | 1.401 (2) |
C33—O6 | 1.3317 (18) | C17—C18 | 1.375 (2) |
C34—O6 | 1.4534 (19) | C17—H17 | 0.9500 |
C34—H34A | 0.9800 | C18—C19 | 1.382 (2) |
C34—H34B | 0.9800 | C18—H18 | 0.9500 |
C34—H34C | 0.9800 | C19—C20 | 1.389 (2) |
C1—C2 | 1.512 (2) | C19—H19 | 0.9500 |
C1—C27 | 1.516 (2) | C20—C21 | 1.397 (2) |
C1—H1A | 0.9900 | C20—C22 | 1.516 (2) |
C1—H1B | 0.9900 | C21—O4 | 1.3569 (17) |
C2—C3 | 1.393 (2) | C22—C23 | 1.521 (2) |
C2—C7 | 1.398 (2) | C22—H22A | 0.9900 |
C3—C4 | 1.381 (2) | C22—H22B | 0.9900 |
C3—H3 | 0.9500 | C23—C24 | 1.390 (2) |
C4—C5 | 1.380 (2) | C23—C28 | 1.3925 (19) |
C4—H4 | 0.9500 | C24—C25 | 1.381 (2) |
C5—C6 | 1.387 (2) | C24—H24 | 0.9500 |
C5—H5 | 0.9500 | C25—C26 | 1.383 (2) |
C6—C7 | 1.399 (2) | C25—H25 | 0.9500 |
C6—C8 | 1.514 (2) | C26—C27 | 1.390 (2) |
C7—O2 | 1.3587 (18) | C26—H26 | 0.9500 |
C8—C9 | 1.514 (2) | C27—C28 | 1.391 (2) |
C8—H8A | 0.9900 | C28—O3 | 1.4018 (16) |
C8—H8B | 0.9900 | C29—O3 | 1.4212 (16) |
C9—C10 | 1.388 (2) | C29—C30 | 1.496 (2) |
C9—C14 | 1.391 (2) | C29—H29A | 0.9900 |
C10—C11 | 1.382 (2) | C29—H29B | 0.9900 |
C10—H10 | 0.9500 | C30—O7 | 1.1883 (17) |
C11—C12 | 1.376 (2) | C30—O8 | 1.3314 (17) |
C11—H11 | 0.9500 | O2—H2 | 0.8400 |
C12—C13 | 1.385 (2) | O4—H4A | 0.8400 |
O8—C31—H31A | 109.5 | C13—C14—C9 | 122.73 (13) |
O8—C31—H31B | 109.4 | C13—C14—O1 | 117.55 (13) |
H31A—C31—H31B | 109.5 | C9—C14—O1 | 119.66 (13) |
O8—C31—H31C | 109.5 | C16—C15—C13 | 111.63 (12) |
H31A—C31—H31C | 109.5 | C16—C15—H15A | 109.3 |
H31B—C31—H31C | 109.5 | C13—C15—H15A | 109.3 |
O1—C32—C33 | 107.43 (12) | C16—C15—H15B | 109.3 |
O1—C32—H32A | 110.2 | C13—C15—H15B | 109.3 |
C33—C32—H32A | 110.2 | H15A—C15—H15B | 108.0 |
O1—C32—H32B | 110.2 | C17—C16—C21 | 117.99 (15) |
C33—C32—H32B | 110.2 | C17—C16—C15 | 120.36 (14) |
H32A—C32—H32B | 108.5 | C21—C16—C15 | 121.64 (14) |
O5—C33—O6 | 125.06 (14) | C18—C17—C16 | 121.55 (15) |
O5—C33—C32 | 124.77 (14) | C18—C17—H17 | 119.2 |
O6—C33—C32 | 110.16 (13) | C16—C17—H17 | 119.2 |
O6—C34—H34A | 109.5 | C17—C18—C19 | 119.63 (15) |
O6—C34—H34B | 109.5 | C17—C18—H18 | 120.2 |
H34A—C34—H34B | 109.5 | C19—C18—H18 | 120.2 |
O6—C34—H34C | 109.5 | C18—C19—C20 | 121.13 (15) |
H34A—C34—H34C | 109.5 | C18—C19—H19 | 119.4 |
H34B—C34—H34C | 109.5 | C20—C19—H19 | 119.4 |
C2—C1—C27 | 113.07 (11) | C19—C20—C21 | 118.33 (14) |
C2—C1—H1A | 109.0 | C19—C20—C22 | 120.69 (14) |
C27—C1—H1A | 109.0 | C21—C20—C22 | 120.98 (13) |
C2—C1—H1B | 109.0 | O4—C21—C20 | 115.68 (12) |
C27—C1—H1B | 109.0 | O4—C21—C16 | 122.97 (13) |
H1A—C1—H1B | 107.8 | C20—C21—C16 | 121.33 (13) |
C3—C2—C7 | 117.80 (14) | C20—C22—C23 | 113.31 (12) |
C3—C2—C1 | 120.21 (14) | C20—C22—H22A | 108.9 |
C7—C2—C1 | 121.99 (13) | C23—C22—H22A | 108.9 |
C4—C3—C2 | 121.75 (16) | C20—C22—H22B | 108.9 |
C4—C3—H3 | 119.1 | C23—C22—H22B | 108.9 |
C2—C3—H3 | 119.1 | H22A—C22—H22B | 107.7 |
C5—C4—C3 | 119.34 (15) | C24—C23—C28 | 116.89 (13) |
C5—C4—H4 | 120.3 | C24—C23—C22 | 121.17 (13) |
C3—C4—H4 | 120.3 | C28—C23—C22 | 121.93 (13) |
C4—C5—C6 | 121.18 (15) | C25—C24—C23 | 121.55 (13) |
C4—C5—H5 | 119.4 | C25—C24—H24 | 119.2 |
C6—C5—H5 | 119.4 | C23—C24—H24 | 119.2 |
C5—C6—C7 | 118.67 (15) | C24—C25—C26 | 119.96 (13) |
C5—C6—C8 | 121.39 (14) | C24—C25—H25 | 120.0 |
C7—C6—C8 | 119.93 (14) | C26—C25—H25 | 120.0 |
O2—C7—C2 | 123.64 (13) | C25—C26—C27 | 120.57 (13) |
O2—C7—C6 | 115.08 (13) | C25—C26—H26 | 119.7 |
C2—C7—C6 | 121.24 (14) | C27—C26—H26 | 119.7 |
C9—C8—C6 | 113.26 (12) | C26—C27—C28 | 117.88 (12) |
C9—C8—H8A | 108.9 | C26—C27—C1 | 120.96 (13) |
C6—C8—H8A | 108.9 | C28—C27—C1 | 121.15 (13) |
C9—C8—H8B | 108.9 | C27—C28—C23 | 122.91 (13) |
C6—C8—H8B | 108.9 | C27—C28—O3 | 117.64 (12) |
H8A—C8—H8B | 107.7 | C23—C28—O3 | 119.42 (12) |
C10—C9—C14 | 117.06 (14) | O3—C29—C30 | 108.29 (11) |
C10—C9—C8 | 120.24 (14) | O3—C29—H29A | 110.0 |
C14—C9—C8 | 122.70 (13) | C30—C29—H29A | 110.1 |
C11—C10—C9 | 121.46 (15) | O3—C29—H29B | 110.0 |
C11—C10—H10 | 119.3 | C30—C29—H29B | 110.0 |
C9—C10—H10 | 119.3 | H29A—C29—H29B | 108.4 |
C12—C11—C10 | 119.70 (15) | O7—C30—O8 | 124.88 (13) |
C12—C11—H11 | 120.2 | O7—C30—C29 | 124.97 (13) |
C10—C11—H11 | 120.1 | O8—C30—C29 | 110.13 (12) |
C11—C12—C13 | 121.06 (15) | C7—O2—H2 | 109.5 |
C11—C12—H12 | 119.5 | C14—O1—C32 | 113.33 (10) |
C13—C12—H12 | 119.5 | C28—O3—C29 | 113.38 (10) |
C12—C13—C14 | 117.77 (14) | C21—O4—H4A | 109.5 |
C12—C13—C15 | 120.40 (14) | C33—O6—C34 | 115.62 (13) |
C14—C13—C15 | 121.73 (13) | C30—O8—C31 | 116.11 (12) |
O1—C32—C33—O5 | −18.6 (2) | C17—C18—C19—C20 | −0.3 (3) |
O1—C32—C33—O6 | 162.14 (12) | C18—C19—C20—C21 | 2.0 (2) |
C27—C1—C2—C3 | −107.33 (15) | C18—C19—C20—C22 | −178.63 (14) |
C27—C1—C2—C7 | 72.80 (18) | C19—C20—C21—O4 | 176.15 (13) |
C7—C2—C3—C4 | −0.1 (2) | C22—C20—C21—O4 | −3.18 (19) |
C1—C2—C3—C4 | 179.99 (13) | C19—C20—C21—C16 | −2.2 (2) |
C2—C3—C4—C5 | −0.4 (2) | C22—C20—C21—C16 | 178.52 (13) |
C3—C4—C5—C6 | 0.3 (2) | C17—C16—C21—O4 | −177.63 (14) |
C4—C5—C6—C7 | 0.5 (2) | C15—C16—C21—O4 | 3.1 (2) |
C4—C5—C6—C8 | 179.08 (14) | C17—C16—C21—C20 | 0.5 (2) |
C3—C2—C7—O2 | −176.85 (13) | C15—C16—C21—C20 | −178.70 (13) |
C1—C2—C7—O2 | 3.0 (2) | C19—C20—C22—C23 | 99.81 (16) |
C3—C2—C7—C6 | 0.9 (2) | C21—C20—C22—C23 | −80.88 (17) |
C1—C2—C7—C6 | −179.21 (13) | C20—C22—C23—C24 | −76.00 (17) |
C5—C6—C7—O2 | 176.84 (13) | C20—C22—C23—C28 | 102.80 (15) |
C8—C6—C7—O2 | −1.75 (19) | C28—C23—C24—C25 | −2.2 (2) |
C5—C6—C7—C2 | −1.1 (2) | C22—C23—C24—C25 | 176.61 (13) |
C8—C6—C7—C2 | −179.70 (13) | C23—C24—C25—C26 | −1.8 (2) |
C5—C6—C8—C9 | 104.44 (16) | C24—C25—C26—C27 | 3.0 (2) |
C7—C6—C8—C9 | −77.01 (17) | C25—C26—C27—C28 | 0.0 (2) |
C6—C8—C9—C10 | −72.20 (18) | C25—C26—C27—C1 | −178.71 (12) |
C6—C8—C9—C14 | 106.82 (16) | C2—C1—C27—C26 | 80.57 (17) |
C14—C9—C10—C11 | −0.5 (2) | C2—C1—C27—C28 | −98.09 (16) |
C8—C9—C10—C11 | 178.55 (14) | C26—C27—C28—C23 | −4.3 (2) |
C9—C10—C11—C12 | −2.9 (2) | C1—C27—C28—C23 | 174.40 (12) |
C10—C11—C12—C13 | 2.5 (2) | C26—C27—C28—O3 | 177.63 (11) |
C11—C12—C13—C14 | 1.5 (2) | C1—C27—C28—O3 | −3.67 (18) |
C11—C12—C13—C15 | −174.99 (14) | C24—C23—C28—C27 | 5.4 (2) |
C12—C13—C14—C9 | −5.1 (2) | C22—C23—C28—C27 | −173.47 (12) |
C15—C13—C14—C9 | 171.26 (13) | C24—C23—C28—O3 | −176.58 (11) |
C12—C13—C14—O1 | 177.63 (12) | C22—C23—C28—O3 | 4.57 (19) |
C15—C13—C14—O1 | −6.0 (2) | O3—C29—C30—O7 | −18.4 (2) |
C10—C9—C14—C13 | 4.7 (2) | O3—C29—C30—O8 | 162.94 (11) |
C8—C9—C14—C13 | −174.40 (13) | C13—C14—O1—C32 | −94.09 (15) |
C10—C9—C14—O1 | −178.17 (12) | C9—C14—O1—C32 | 88.58 (16) |
C8—C9—C14—O1 | 2.8 (2) | C33—C32—O1—C14 | 167.04 (12) |
C12—C13—C15—C16 | 77.23 (17) | C27—C28—O3—C29 | −95.19 (14) |
C14—C13—C15—C16 | −99.07 (17) | C23—C28—O3—C29 | 86.68 (15) |
C13—C15—C16—C17 | −102.87 (17) | C30—C29—O3—C28 | 166.48 (11) |
C13—C15—C16—C21 | 76.36 (18) | O5—C33—O6—C34 | 0.3 (2) |
C21—C16—C17—C18 | 1.3 (2) | C32—C33—O6—C34 | 179.61 (13) |
C15—C16—C17—C18 | −179.49 (15) | O7—C30—O8—C31 | −0.5 (2) |
C16—C17—C18—C19 | −1.4 (3) | C29—C30—O8—C31 | 178.17 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.92 | 2.7273 (14) | 160 |
O4—H4A···O1 | 0.84 | 1.99 | 2.7987 (15) | 161 |
O2—H2···O7 | 0.84 | 2.88 | 3.4142 (16) | 124 |
O4—H4A···O5 | 0.84 | 2.90 | 3.4434 (16) | 124 |
C36H36O8·CH3Cl | F(000) = 748 |
Mr = 716.02 | Dx = 1.397 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.027 (2) Å | Cell parameters from 14325 reflections |
b = 10.243 (2) Å | θ = 1–27.5° |
c = 16.852 (3) Å | µ = 0.32 mm−1 |
β = 100.39 (3)° | T = 100 K |
V = 1702.6 (6) Å3 | Block, colourless |
Z = 2 | 0.10 × 0.08 × 0.06 mm |
Nonius KappaCCD area-detector diffractometer | 6130 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.052 |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | θmax = 27.5°, θmin = 2.5° |
Tmin = 0.969, Tmax = 0.981 | h = −13→13 |
24715 measured reflections | k = −13→13 |
7629 independent reflections | l = −21→21 |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max = 0.03 |
R[F2 > 2σ(F2)] = 0.041 | Δρmax = 0.29 e Å−3 |
wR(F2) = 0.100 | Δρmin = −0.25 e Å−3 |
S = 0.95 | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
7629 reflections | Extinction coefficient: 0.0153 (14) |
438 parameters | Absolute structure: Flack (1983) |
1 restraint | Absolute structure parameter: −0.10 (4) |
H-atom parameters constrained |
C36H36O8·CH3Cl | V = 1702.6 (6) Å3 |
Mr = 716.02 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.027 (2) Å | µ = 0.32 mm−1 |
b = 10.243 (2) Å | T = 100 K |
c = 16.852 (3) Å | 0.10 × 0.08 × 0.06 mm |
β = 100.39 (3)° |
Nonius KappaCCD area-detector diffractometer | 7629 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 6130 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.981 | Rint = 0.052 |
24715 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.100 | Δρmax = 0.29 e Å−3 |
S = 0.95 | Δρmin = −0.25 e Å−3 |
7629 reflections | Absolute structure: Flack (1983) |
438 parameters | Absolute structure parameter: −0.10 (4) |
1 restraint |
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 | 0.6949 (2) | 0.7611 (2) | 0.20101 (13) | 0.0240 (5) | |
C2 | 0.8342 (2) | 0.7631 (2) | 0.20199 (13) | 0.0274 (5) | |
H2 | 0.8674 | 0.7599 | 0.1527 | 0.033* | |
C3 | 0.9247 (2) | 0.7698 (2) | 0.27465 (14) | 0.0292 (5) | |
H3 | 1.0194 | 0.7721 | 0.2748 | 0.035* | |
C4 | 0.8776 (2) | 0.7730 (2) | 0.34662 (13) | 0.0263 (5) | |
H4 | 0.9407 | 0.7761 | 0.3959 | 0.032* | |
C5 | 0.7389 (2) | 0.7717 (2) | 0.34842 (13) | 0.0238 (5) | |
C6 | 0.6497 (2) | 0.7684 (2) | 0.27421 (12) | 0.0226 (5) | |
C7 | 0.6919 (2) | 0.7688 (2) | 0.42875 (12) | 0.0264 (5) | |
H7A | 0.5927 | 0.7833 | 0.4200 | 0.032* | |
H7B | 0.7363 | 0.8403 | 0.4632 | 0.032* | |
C8 | 0.7250 (2) | 0.6401 (2) | 0.47125 (12) | 0.0249 (5) | |
C9 | 0.8421 (2) | 0.6223 (2) | 0.52891 (13) | 0.0296 (5) | |
H9 | 0.9022 | 0.6936 | 0.5433 | 0.036* | |
C10 | 0.8721 (2) | 0.5024 (2) | 0.56551 (13) | 0.0322 (6) | |
H10 | 0.9517 | 0.4918 | 0.6051 | 0.039* | |
C11 | 0.7860 (2) | 0.3987 (3) | 0.54424 (13) | 0.0305 (5) | |
H11 | 0.8070 | 0.3168 | 0.5699 | 0.037* | |
C12 | 0.6687 (2) | 0.4105 (2) | 0.48588 (13) | 0.0262 (5) | |
C13 | 0.6389 (2) | 0.5334 (2) | 0.45111 (12) | 0.0245 (5) | |
C14 | 0.5782 (2) | 0.2921 (2) | 0.46107 (13) | 0.0290 (5) | |
H14A | 0.5970 | 0.2248 | 0.5038 | 0.035* | |
H14B | 0.4821 | 0.3184 | 0.4560 | 0.035* | |
C15 | 0.6005 (2) | 0.2338 (2) | 0.38182 (13) | 0.0254 (5) | |
C16 | 0.7087 (2) | 0.1504 (2) | 0.37861 (14) | 0.0290 (5) | |
H16 | 0.7672 | 0.1259 | 0.4271 | 0.035* | |
C17 | 0.7324 (2) | 0.1026 (2) | 0.30549 (15) | 0.0294 (5) | |
H17 | 0.8052 | 0.0437 | 0.3043 | 0.035* | |
C18 | 0.6502 (2) | 0.1404 (2) | 0.23423 (15) | 0.0285 (5) | |
H18 | 0.6687 | 0.1089 | 0.1843 | 0.034* | |
C19 | 0.5406 (2) | 0.2240 (2) | 0.23463 (13) | 0.0238 (5) | |
C20 | 0.5159 (2) | 0.2657 (2) | 0.30901 (13) | 0.0228 (5) | |
C21 | 0.4574 (2) | 0.2692 (2) | 0.15481 (13) | 0.0247 (5) | |
H21A | 0.4350 | 0.1930 | 0.1188 | 0.030* | |
H21B | 0.3712 | 0.3076 | 0.1646 | 0.030* | |
C22 | 0.5326 (2) | 0.3693 (2) | 0.11360 (12) | 0.0237 (5) | |
C23 | 0.6129 (2) | 0.3321 (3) | 0.05827 (13) | 0.0282 (5) | |
H23 | 0.6186 | 0.2424 | 0.0449 | 0.034* | |
C24 | 0.6847 (2) | 0.4233 (3) | 0.02247 (13) | 0.0327 (6) | |
H24 | 0.7384 | 0.3967 | −0.0157 | 0.039* | |
C25 | 0.6776 (2) | 0.5529 (2) | 0.04276 (13) | 0.0287 (5) | |
H25 | 0.7280 | 0.6151 | 0.0185 | 0.034* | |
C26 | 0.5990 (2) | 0.5956 (2) | 0.09756 (12) | 0.0238 (5) | |
C27 | 0.5261 (2) | 0.5019 (2) | 0.13216 (12) | 0.0214 (5) | |
C28 | 0.5985 (2) | 0.7382 (2) | 0.12169 (13) | 0.0259 (5) | |
H28A | 0.5056 | 0.7643 | 0.1273 | 0.031* | |
H28B | 0.6263 | 0.7928 | 0.0790 | 0.031* | |
C29 | 0.4400 (2) | 0.8813 (2) | 0.27686 (16) | 0.0342 (6) | |
H29A | 0.4972 | 0.9550 | 0.2651 | 0.041* | |
H29B | 0.4201 | 0.8933 | 0.3318 | 0.041* | |
C30 | 0.3107 (2) | 0.8790 (2) | 0.21677 (13) | 0.0242 (5) | |
C31 | 0.1150 (3) | 0.9994 (3) | 0.16073 (15) | 0.0449 (7) | |
H31A | 0.0738 | 0.9115 | 0.1520 | 0.054* | |
H31B | 0.1325 | 1.0320 | 0.1083 | 0.054* | |
C32 | 0.0213 (3) | 1.0874 (3) | 0.19128 (15) | 0.0377 (6) | |
H32A | 0.0179 | 1.0651 | 0.2474 | 0.057* | |
H32B | −0.0694 | 1.0784 | 0.1584 | 0.057* | |
H32C | 0.0526 | 1.1776 | 0.1884 | 0.057* | |
C33 | 0.2809 (2) | 0.2891 (2) | 0.31157 (15) | 0.0297 (5) | |
H33A | 0.2923 | 0.2072 | 0.3433 | 0.036* | |
H33B | 0.2387 | 0.2679 | 0.2553 | 0.036* | |
C34 | 0.1931 (2) | 0.3843 (2) | 0.34768 (13) | 0.0253 (5) | |
C35 | −0.0389 (2) | 0.4354 (3) | 0.35154 (14) | 0.0318 (6) | |
H35A | −0.0033 | 0.5245 | 0.3644 | 0.038* | |
H35B | −0.0608 | 0.3961 | 0.4013 | 0.038* | |
C36 | −0.1627 (2) | 0.4406 (2) | 0.28741 (14) | 0.0311 (5) | |
H36A | −0.1404 | 0.4820 | 0.2390 | 0.047* | |
H36B | −0.2331 | 0.4915 | 0.3068 | 0.047* | |
H36C | −0.1958 | 0.3518 | 0.2743 | 0.047* | |
C37 | −0.1481 (2) | 1.0586 (2) | −0.07061 (13) | 0.0286 (5) | |
H37 | −0.2299 | 1.1002 | −0.1037 | 0.034* | |
O1 | 0.50990 (14) | 0.76174 (15) | 0.27263 (8) | 0.0231 (3) | |
O2 | 0.52623 (16) | 0.56023 (16) | 0.39538 (9) | 0.0300 (4) | |
H2A | 0.4816 | 0.4913 | 0.3837 | 0.045* | |
O3 | 0.40849 (14) | 0.35053 (15) | 0.31349 (9) | 0.0232 (3) | |
O4 | 0.44131 (15) | 0.53302 (15) | 0.18481 (9) | 0.0255 (3) | |
H4A | 0.4662 | 0.6039 | 0.2079 | 0.038* | |
O5 | 0.27314 (19) | 0.7906 (2) | 0.17372 (12) | 0.0494 (5) | |
O6 | 0.24262 (17) | 0.99057 (17) | 0.21792 (10) | 0.0361 (4) | |
O7 | 0.23446 (16) | 0.46840 (19) | 0.39445 (10) | 0.0375 (4) | |
O8 | 0.06216 (15) | 0.35562 (16) | 0.32079 (9) | 0.0276 (4) | |
Cl1 | −0.06484 (8) | 0.96828 (8) | −0.13453 (5) | 0.0563 (2) | |
Cl2 | −0.04219 (6) | 1.18233 (6) | −0.02198 (3) | 0.03249 (15) | |
Cl3 | −0.20159 (7) | 0.95519 (7) | 0.00142 (4) | 0.04352 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0228 (12) | 0.0183 (11) | 0.0297 (11) | −0.0010 (10) | 0.0012 (9) | 0.0036 (9) |
C2 | 0.0266 (13) | 0.0247 (12) | 0.0301 (12) | −0.0023 (10) | 0.0032 (10) | 0.0045 (10) |
C3 | 0.0196 (12) | 0.0263 (13) | 0.0407 (13) | −0.0040 (10) | 0.0028 (10) | 0.0049 (11) |
C4 | 0.0230 (12) | 0.0187 (12) | 0.0341 (12) | 0.0026 (10) | −0.0030 (9) | 0.0001 (10) |
C5 | 0.0226 (12) | 0.0158 (11) | 0.0307 (12) | −0.0004 (9) | −0.0009 (9) | −0.0023 (9) |
C6 | 0.0197 (12) | 0.0163 (11) | 0.0303 (12) | −0.0004 (9) | 0.0000 (9) | 0.0010 (9) |
C7 | 0.0247 (12) | 0.0286 (13) | 0.0239 (11) | 0.0027 (11) | −0.0012 (9) | −0.0040 (10) |
C8 | 0.0241 (12) | 0.0305 (13) | 0.0197 (10) | 0.0046 (10) | 0.0032 (8) | −0.0047 (9) |
C9 | 0.0278 (13) | 0.0342 (14) | 0.0249 (11) | 0.0042 (11) | −0.0005 (9) | −0.0082 (10) |
C10 | 0.0316 (14) | 0.0389 (15) | 0.0225 (11) | 0.0105 (12) | −0.0048 (10) | −0.0056 (10) |
C11 | 0.0327 (14) | 0.0348 (14) | 0.0236 (12) | 0.0084 (11) | 0.0036 (10) | 0.0019 (10) |
C12 | 0.0252 (12) | 0.0334 (13) | 0.0209 (11) | 0.0026 (10) | 0.0062 (9) | 0.0015 (9) |
C13 | 0.0190 (12) | 0.0325 (14) | 0.0213 (11) | 0.0065 (10) | 0.0018 (8) | −0.0003 (9) |
C14 | 0.0276 (13) | 0.0314 (14) | 0.0281 (12) | 0.0048 (11) | 0.0051 (9) | 0.0097 (10) |
C15 | 0.0219 (12) | 0.0214 (12) | 0.0325 (12) | −0.0024 (9) | 0.0043 (9) | 0.0069 (9) |
C16 | 0.0207 (12) | 0.0239 (13) | 0.0411 (14) | 0.0008 (10) | 0.0022 (10) | 0.0093 (10) |
C17 | 0.0215 (12) | 0.0202 (12) | 0.0476 (15) | 0.0010 (10) | 0.0094 (10) | 0.0035 (10) |
C18 | 0.0245 (13) | 0.0229 (13) | 0.0384 (13) | −0.0016 (10) | 0.0065 (10) | −0.0012 (10) |
C19 | 0.0218 (12) | 0.0163 (11) | 0.0334 (12) | −0.0036 (9) | 0.0055 (9) | −0.0019 (9) |
C20 | 0.0166 (11) | 0.0170 (11) | 0.0354 (12) | 0.0012 (9) | 0.0065 (9) | 0.0026 (9) |
C21 | 0.0210 (11) | 0.0235 (12) | 0.0287 (11) | 0.0002 (10) | 0.0022 (9) | −0.0076 (9) |
C22 | 0.0203 (12) | 0.0295 (14) | 0.0196 (11) | 0.0000 (10) | −0.0015 (8) | −0.0020 (9) |
C23 | 0.0245 (13) | 0.0325 (14) | 0.0268 (12) | 0.0035 (10) | 0.0027 (9) | −0.0094 (10) |
C24 | 0.0299 (14) | 0.0478 (17) | 0.0218 (11) | 0.0041 (12) | 0.0087 (10) | −0.0018 (10) |
C25 | 0.0239 (13) | 0.0379 (15) | 0.0243 (12) | −0.0025 (11) | 0.0041 (9) | 0.0026 (10) |
C26 | 0.0208 (12) | 0.0295 (13) | 0.0199 (11) | −0.0006 (10) | 0.0003 (9) | 0.0013 (9) |
C27 | 0.0170 (11) | 0.0283 (13) | 0.0178 (10) | 0.0029 (9) | 0.0003 (8) | −0.0012 (9) |
C28 | 0.0231 (12) | 0.0282 (13) | 0.0257 (11) | −0.0020 (10) | 0.0024 (9) | 0.0076 (9) |
C29 | 0.0254 (13) | 0.0252 (14) | 0.0486 (15) | 0.0066 (11) | −0.0024 (11) | −0.0081 (11) |
C30 | 0.0212 (12) | 0.0232 (13) | 0.0284 (12) | 0.0039 (10) | 0.0051 (9) | 0.0017 (10) |
C31 | 0.0337 (15) | 0.065 (2) | 0.0325 (14) | 0.0191 (14) | −0.0035 (11) | −0.0030 (13) |
C32 | 0.0310 (14) | 0.0409 (16) | 0.0392 (15) | 0.0032 (12) | 0.0010 (11) | −0.0085 (12) |
C33 | 0.0200 (12) | 0.0278 (14) | 0.0419 (14) | −0.0019 (11) | 0.0078 (10) | −0.0031 (10) |
C34 | 0.0203 (12) | 0.0269 (13) | 0.0292 (12) | 0.0013 (10) | 0.0059 (9) | 0.0066 (10) |
C35 | 0.0235 (13) | 0.0353 (15) | 0.0383 (13) | 0.0063 (11) | 0.0096 (10) | −0.0036 (11) |
C36 | 0.0236 (13) | 0.0281 (14) | 0.0416 (14) | 0.0009 (11) | 0.0060 (10) | 0.0021 (11) |
C37 | 0.0260 (13) | 0.0302 (14) | 0.0289 (12) | −0.0030 (11) | 0.0028 (10) | 0.0018 (10) |
O1 | 0.0162 (8) | 0.0204 (8) | 0.0315 (8) | 0.0017 (6) | 0.0010 (6) | 0.0001 (7) |
O2 | 0.0255 (9) | 0.0275 (9) | 0.0325 (9) | −0.0018 (7) | −0.0065 (7) | 0.0043 (7) |
O3 | 0.0163 (8) | 0.0221 (8) | 0.0312 (8) | −0.0001 (7) | 0.0047 (6) | 0.0020 (6) |
O4 | 0.0257 (9) | 0.0227 (9) | 0.0300 (8) | −0.0027 (7) | 0.0101 (6) | −0.0035 (6) |
O5 | 0.0357 (11) | 0.0448 (12) | 0.0581 (12) | 0.0122 (9) | −0.0175 (9) | −0.0221 (10) |
O6 | 0.0283 (9) | 0.0329 (11) | 0.0440 (10) | 0.0110 (8) | −0.0016 (7) | −0.0010 (8) |
O7 | 0.0258 (9) | 0.0458 (11) | 0.0405 (10) | −0.0011 (9) | 0.0046 (7) | −0.0167 (9) |
O8 | 0.0192 (8) | 0.0278 (9) | 0.0360 (9) | 0.0025 (7) | 0.0056 (6) | −0.0012 (7) |
Cl1 | 0.0497 (4) | 0.0625 (5) | 0.0613 (5) | −0.0083 (4) | 0.0224 (3) | −0.0275 (4) |
Cl2 | 0.0317 (3) | 0.0304 (3) | 0.0330 (3) | −0.0039 (3) | −0.0004 (2) | 0.0026 (2) |
Cl3 | 0.0426 (4) | 0.0462 (4) | 0.0388 (3) | −0.0154 (3) | −0.0004 (3) | 0.0137 (3) |
C1—C6 | 1.390 (3) | C22—C27 | 1.398 (3) |
C1—C2 | 1.395 (3) | C23—C24 | 1.382 (4) |
C1—C28 | 1.520 (3) | C23—H23 | 0.9500 |
C2—C3 | 1.388 (3) | C24—C25 | 1.376 (4) |
C2—H2 | 0.9500 | C24—H24 | 0.9500 |
C3—C4 | 1.379 (3) | C25—C26 | 1.388 (3) |
C3—H3 | 0.9500 | C25—H25 | 0.9500 |
C4—C5 | 1.396 (3) | C26—C27 | 1.396 (3) |
C4—H4 | 0.9500 | C26—C28 | 1.517 (3) |
C5—C6 | 1.401 (3) | C27—O4 | 1.372 (3) |
C5—C7 | 1.512 (3) | C28—H28A | 0.9900 |
C6—O1 | 1.399 (3) | C28—H28B | 0.9900 |
C7—C8 | 1.508 (3) | C29—O1 | 1.419 (3) |
C7—H7A | 0.9900 | C29—C30 | 1.495 (3) |
C7—H7B | 0.9900 | C29—H29A | 0.9900 |
C8—C9 | 1.395 (3) | C29—H29B | 0.9900 |
C8—C13 | 1.396 (3) | C30—O5 | 1.179 (3) |
C9—C10 | 1.382 (3) | C30—O6 | 1.333 (3) |
C9—H9 | 0.9500 | C31—O6 | 1.459 (3) |
C10—C11 | 1.375 (4) | C31—C32 | 1.461 (4) |
C10—H10 | 0.9500 | C31—H31A | 0.9900 |
C11—C12 | 1.396 (3) | C31—H31B | 0.9900 |
C11—H11 | 0.9500 | C32—H32A | 0.9800 |
C12—C13 | 1.398 (3) | C32—H32B | 0.9800 |
C12—C14 | 1.527 (3) | C32—H32C | 0.9800 |
C13—O2 | 1.360 (3) | C33—O3 | 1.421 (3) |
C14—C15 | 1.516 (3) | C33—C34 | 1.513 (3) |
C14—H14A | 0.9900 | C33—H33A | 0.9900 |
C14—H14B | 0.9900 | C33—H33B | 0.9900 |
C15—C16 | 1.390 (3) | C34—O7 | 1.191 (3) |
C15—C20 | 1.399 (3) | C34—O8 | 1.342 (3) |
C16—C17 | 1.386 (3) | C35—O8 | 1.467 (3) |
C16—H16 | 0.9500 | C35—C36 | 1.492 (3) |
C17—C18 | 1.384 (3) | C35—H35A | 0.9900 |
C17—H17 | 0.9500 | C35—H35B | 0.9900 |
C18—C19 | 1.395 (3) | C36—H36A | 0.9800 |
C18—H18 | 0.9500 | C36—H36B | 0.9800 |
C19—C20 | 1.388 (3) | C36—H36C | 0.9800 |
C19—C21 | 1.522 (3) | C37—Cl1 | 1.743 (2) |
C20—O3 | 1.396 (3) | C37—Cl2 | 1.758 (2) |
C21—C22 | 1.514 (3) | C37—Cl3 | 1.766 (2) |
C21—H21A | 0.9900 | C37—H37 | 1.0000 |
C21—H21B | 0.9900 | O2—H2A | 0.8400 |
C22—C23 | 1.391 (3) | O4—H4A | 0.8400 |
C6—C1—C2 | 118.32 (19) | C24—C23—C22 | 121.2 (2) |
C6—C1—C28 | 122.12 (19) | C24—C23—H23 | 119.4 |
C2—C1—C28 | 119.3 (2) | C22—C23—H23 | 119.4 |
C3—C2—C1 | 120.3 (2) | C25—C24—C23 | 119.3 (2) |
C3—C2—H2 | 119.8 | C25—C24—H24 | 120.4 |
C1—C2—H2 | 119.8 | C23—C24—H24 | 120.4 |
C4—C3—C2 | 120.3 (2) | C24—C25—C26 | 122.0 (2) |
C4—C3—H3 | 119.9 | C24—C25—H25 | 119.0 |
C2—C3—H3 | 119.9 | C26—C25—H25 | 119.0 |
C3—C4—C5 | 121.3 (2) | C25—C26—C27 | 117.7 (2) |
C3—C4—H4 | 119.4 | C25—C26—C28 | 120.8 (2) |
C5—C4—H4 | 119.4 | C27—C26—C28 | 121.51 (19) |
C4—C5—C6 | 117.3 (2) | O4—C27—C26 | 122.9 (2) |
C4—C5—C7 | 119.48 (19) | O4—C27—C22 | 115.5 (2) |
C6—C5—C7 | 123.2 (2) | C26—C27—C22 | 121.7 (2) |
C1—C6—C5 | 122.4 (2) | C26—C28—C1 | 110.62 (18) |
C1—C6—O1 | 117.76 (18) | C26—C28—H28A | 109.5 |
C5—C6—O1 | 119.64 (19) | C1—C28—H28A | 109.5 |
C5—C7—C8 | 111.43 (18) | C26—C28—H28B | 109.5 |
C5—C7—H7A | 109.3 | C1—C28—H28B | 109.5 |
C8—C7—H7A | 109.3 | H28A—C28—H28B | 108.1 |
C5—C7—H7B | 109.3 | O1—C29—C30 | 109.17 (19) |
C8—C7—H7B | 109.3 | O1—C29—H29A | 109.8 |
H7A—C7—H7B | 108.0 | C30—C29—H29A | 109.8 |
C9—C8—C13 | 118.2 (2) | O1—C29—H29B | 109.8 |
C9—C8—C7 | 122.1 (2) | C30—C29—H29B | 109.8 |
C13—C8—C7 | 119.67 (19) | H29A—C29—H29B | 108.3 |
C10—C9—C8 | 121.0 (2) | O5—C30—O6 | 124.1 (2) |
C10—C9—H9 | 119.5 | O5—C30—C29 | 124.8 (2) |
C8—C9—H9 | 119.5 | O6—C30—C29 | 111.13 (19) |
C11—C10—C9 | 119.6 (2) | O6—C31—C32 | 110.4 (2) |
C11—C10—H10 | 120.2 | O6—C31—H31A | 109.6 |
C9—C10—H10 | 120.2 | C32—C31—H31A | 109.6 |
C10—C11—C12 | 121.7 (2) | O6—C31—H31B | 109.6 |
C10—C11—H11 | 119.1 | C32—C31—H31B | 109.6 |
C12—C11—H11 | 119.1 | H31A—C31—H31B | 108.1 |
C13—C12—C11 | 117.5 (2) | C31—C32—H32A | 109.5 |
C13—C12—C14 | 122.0 (2) | C31—C32—H32B | 109.5 |
C11—C12—C14 | 120.5 (2) | H32A—C32—H32B | 109.5 |
O2—C13—C12 | 124.0 (2) | C31—C32—H32C | 109.5 |
O2—C13—C8 | 114.2 (2) | H32A—C32—H32C | 109.5 |
C12—C13—C8 | 121.8 (2) | H32B—C32—H32C | 109.5 |
C15—C14—C12 | 112.28 (18) | O3—C33—C34 | 107.01 (19) |
C15—C14—H14A | 109.1 | O3—C33—H33A | 110.3 |
C12—C14—H14A | 109.1 | C34—C33—H33A | 110.3 |
C15—C14—H14B | 109.1 | O3—C33—H33B | 110.3 |
C12—C14—H14B | 109.1 | C34—C33—H33B | 110.3 |
H14A—C14—H14B | 107.9 | H33A—C33—H33B | 108.6 |
C16—C15—C20 | 117.6 (2) | O7—C34—O8 | 125.8 (2) |
C16—C15—C14 | 121.1 (2) | O7—C34—C33 | 125.0 (2) |
C20—C15—C14 | 121.2 (2) | O8—C34—C33 | 109.2 (2) |
C17—C16—C15 | 120.8 (2) | O8—C35—C36 | 107.53 (18) |
C17—C16—H16 | 119.6 | O8—C35—H35A | 110.2 |
C15—C16—H16 | 119.6 | C36—C35—H35A | 110.2 |
C18—C17—C16 | 120.1 (2) | O8—C35—H35B | 110.2 |
C18—C17—H17 | 119.9 | C36—C35—H35B | 110.2 |
C16—C17—H17 | 119.9 | H35A—C35—H35B | 108.5 |
C17—C18—C19 | 121.0 (2) | C35—C36—H36A | 109.5 |
C17—C18—H18 | 119.5 | C35—C36—H36B | 109.5 |
C19—C18—H18 | 119.5 | H36A—C36—H36B | 109.5 |
C20—C19—C18 | 117.5 (2) | C35—C36—H36C | 109.5 |
C20—C19—C21 | 123.1 (2) | H36A—C36—H36C | 109.5 |
C18—C19—C21 | 119.3 (2) | H36B—C36—H36C | 109.5 |
C19—C20—O3 | 120.34 (19) | Cl1—C37—Cl2 | 110.74 (13) |
C19—C20—C15 | 122.8 (2) | Cl1—C37—Cl3 | 110.17 (14) |
O3—C20—C15 | 116.72 (19) | Cl2—C37—Cl3 | 110.17 (12) |
C22—C21—C19 | 111.87 (18) | Cl1—C37—H37 | 108.6 |
C22—C21—H21A | 109.2 | Cl2—C37—H37 | 108.6 |
C19—C21—H21A | 109.2 | Cl3—C37—H37 | 108.6 |
C22—C21—H21B | 109.2 | C6—O1—C29 | 117.35 (17) |
C19—C21—H21B | 109.2 | C13—O2—H2A | 109.5 |
H21A—C21—H21B | 107.9 | C20—O3—C33 | 115.05 (17) |
C23—C22—C27 | 118.2 (2) | C27—O4—H4A | 109.5 |
C23—C22—C21 | 121.2 (2) | C30—O6—C31 | 115.7 (2) |
C27—C22—C21 | 120.5 (2) | C34—O8—C35 | 117.06 (18) |
C6—C1—C2—C3 | 1.2 (3) | C18—C19—C20—C15 | 4.1 (3) |
C28—C1—C2—C3 | −173.1 (2) | C21—C19—C20—C15 | −173.7 (2) |
C1—C2—C3—C4 | 0.8 (4) | C16—C15—C20—C19 | −4.0 (3) |
C2—C3—C4—C5 | −1.0 (4) | C14—C15—C20—C19 | 173.8 (2) |
C3—C4—C5—C6 | −0.6 (3) | C16—C15—C20—O3 | −179.5 (2) |
C3—C4—C5—C7 | 177.1 (2) | C14—C15—C20—O3 | −1.7 (3) |
C2—C1—C6—C5 | −2.9 (3) | C20—C19—C21—C22 | 104.0 (2) |
C28—C1—C6—C5 | 171.2 (2) | C18—C19—C21—C22 | −73.7 (3) |
C2—C1—C6—O1 | −177.8 (2) | C19—C21—C22—C23 | 91.8 (2) |
C28—C1—C6—O1 | −3.8 (3) | C19—C21—C22—C27 | −86.3 (2) |
C4—C5—C6—C1 | 2.6 (3) | C27—C22—C23—C24 | 0.1 (3) |
C7—C5—C6—C1 | −175.0 (2) | C21—C22—C23—C24 | −178.1 (2) |
C4—C5—C6—O1 | 177.45 (19) | C22—C23—C24—C25 | 0.8 (3) |
C7—C5—C6—O1 | −0.1 (3) | C23—C24—C25—C26 | −0.8 (4) |
C4—C5—C7—C8 | −68.5 (3) | C24—C25—C26—C27 | 0.0 (3) |
C6—C5—C7—C8 | 109.0 (2) | C24—C25—C26—C28 | 177.1 (2) |
C5—C7—C8—C9 | 95.3 (2) | C25—C26—C27—O4 | −177.6 (2) |
C5—C7—C8—C13 | −82.6 (3) | C28—C26—C27—O4 | 5.4 (3) |
C13—C8—C9—C10 | −0.3 (3) | C25—C26—C27—C22 | 0.9 (3) |
C7—C8—C9—C10 | −178.3 (2) | C28—C26—C27—C22 | −176.2 (2) |
C8—C9—C10—C11 | 0.7 (4) | C23—C22—C27—O4 | 177.69 (18) |
C9—C10—C11—C12 | 0.4 (4) | C21—C22—C27—O4 | −4.2 (3) |
C10—C11—C12—C13 | −1.9 (3) | C23—C22—C27—C26 | −0.9 (3) |
C10—C11—C12—C14 | 177.5 (2) | C21—C22—C27—C26 | 177.26 (19) |
C11—C12—C13—O2 | −178.0 (2) | C25—C26—C28—C1 | −97.6 (2) |
C14—C12—C13—O2 | 2.7 (3) | C27—C26—C28—C1 | 79.3 (3) |
C11—C12—C13—C8 | 2.3 (3) | C6—C1—C28—C26 | −98.7 (3) |
C14—C12—C13—C8 | −177.0 (2) | C2—C1—C28—C26 | 75.3 (3) |
C9—C8—C13—O2 | 179.02 (19) | O1—C29—C30—O5 | 0.8 (3) |
C7—C8—C13—O2 | −2.9 (3) | O1—C29—C30—O6 | −179.08 (18) |
C9—C8—C13—C12 | −1.3 (3) | O3—C33—C34—O7 | −25.3 (3) |
C7—C8—C13—C12 | 176.8 (2) | O3—C33—C34—O8 | 156.88 (17) |
C13—C12—C14—C15 | 78.2 (3) | C1—C6—O1—C29 | −98.8 (2) |
C11—C12—C14—C15 | −101.2 (2) | C5—C6—O1—C29 | 86.2 (3) |
C12—C14—C15—C16 | 80.8 (3) | C30—C29—O1—C6 | 136.33 (19) |
C12—C14—C15—C20 | −96.9 (2) | C19—C20—O3—C33 | 85.3 (2) |
C20—C15—C16—C17 | 1.0 (3) | C15—C20—O3—C33 | −99.1 (2) |
C14—C15—C16—C17 | −176.8 (2) | C34—C33—O3—C20 | 159.09 (18) |
C15—C16—C17—C18 | 1.8 (4) | O5—C30—O6—C31 | −0.6 (3) |
C16—C17—C18—C19 | −1.7 (4) | C29—C30—O6—C31 | 179.4 (2) |
C17—C18—C19—C20 | −1.2 (3) | C32—C31—O6—C30 | 152.1 (2) |
C17—C18—C19—C21 | 176.7 (2) | O7—C34—O8—C35 | 0.3 (3) |
C18—C19—C20—O3 | 179.40 (19) | C33—C34—O8—C35 | 178.09 (19) |
C21—C19—C20—O3 | 1.7 (3) | C36—C35—O8—C34 | 149.92 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3 | 0.84 | 1.92 | 2.706 (2) | 154 |
O2—H2A···O7 | 0.84 | 2.53 | 3.071 (2) | 123 |
O4—H4A···O1 | 0.84 | 1.96 | 2.790 (2) | 172 |
O4—H4A···O5 | 0.84 | 2.71 | 3.119 (3) | 112 |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C34H32O8 | C36H36O8·CH3Cl |
Mr | 568.6 | 716.02 |
Crystal system, space group | Rhombohedral, R3 | Monoclinic, P21 |
Temperature (K) | 150 | 100 |
a, b, c (Å) | 32.840 (5), 32.840 (5), 13.918 (3) | 10.027 (2), 10.243 (2), 16.852 (3) |
α, β, γ (°) | 90, 90, 120 | 90, 100.39 (3), 90 |
V (Å3) | 13000 (4) | 1702.6 (6) |
Z | 18 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.32 |
Crystal size (mm) | 0.3 × 0.2 × 0.2 | 0.10 × 0.08 × 0.06 |
Data collection | ||
Diffractometer | Nonius KappaCCD area-detector diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.973, 0.982 | 0.969, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25617, 6609, 4617 | 24715, 7629, 6130 |
Rint | 0.044 | 0.052 |
(sin θ/λ)max (Å−1) | 0.650 | 0.649 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.114, 1.04 | 0.041, 0.100, 0.95 |
No. of reflections | 6609 | 7629 |
No. of parameters | 384 | 438 |
No. of restraints | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.20 | 0.29, −0.25 |
Absolute structure | ? | Flack (1983) |
Absolute structure parameter | ? | −0.10 (4) |
Computer programs: DENZO (Hooft 1998) and COLLECT (Otwinowski & Minor, 1997), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.92 | 2.7273 (14) | 159.8 |
O4—H4A···O1 | 0.84 | 1.99 | 2.7987 (15) | 160.5 |
O2—H2···O7 | 0.84 | 2.88 | 3.4142 (16) | 123.7 |
O4—H4A···O5 | 0.84 | 2.90 | 3.4434 (16) | 124.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O3 | 0.84 | 1.92 | 2.706 (2) | 154.4 |
O2—H2A···O7 | 0.84 | 2.53 | 3.071 (2) | 123.3 |
O4—H4A···O1 | 0.84 | 1.96 | 2.790 (2) | 172.3 |
O4—H4A···O5 | 0.84 | 2.71 | 3.119 (3) | 111.7 |
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There is much current interest in the design of supramolecular structures where the guest–host assembly is formed by non-covalent interactions (Lehn, 1995; Gutsche, 1998). Calixarenes are a promising platform as good candidates for self-assembly (Mandolini & Ungaro, 2000), owing to their high symmetry and ease of chemical modification. The title calix[4]arenes, 2,4-dihydroxy-1,3-bis(methoxycarbonylmethoxy)calix[4]arene, (I), and 2,4-dihydroxy-1,3-bis(ethoxycarbonylmethoxy)calix[4]arene chloroform solvate, (II), are well established in the literature as building blocks for more elaborate calixarenes (Beer et al., 1998). In addition, compound (I) has been shown to extract Cs+ and Sr2+ (Arena et al., 1999; Grunder et al., 1999), however, their crystal structures have not been reported in the literature.
The molecular structures of (I) and (II) are shown in Figs. 1 and 2, respectively, whilst the supramolecular structure of (I) is shown in Fig. 3. The crystal structure of (I) is unusual in that it forms a honeycomb structure of columnar hexagonal tubes. These tubes have an internal diameter of 4.83 (9) Å and are constructed by the stacking of three calixarenes alternatively offset by 60°, giving overall C3 symmetry. The driving force to the formation of this structure is π–π-stacking/interlocking between the calixarene rings and dipole–dipole interactions between the lower rim methyl ester groups. This is demonstrated by the head-to-tail arrangement of the carbonyl groups on the lower rim. To our knowledge, this is the first example of a honeycomb structure for a purely organic calixarene. Calixarene (II) failed to form a nanotubular array, a result of the carbonyl groups on the ethyl ester pendant arms being directed away from each other due to their conformational rearrangement in order to accommodate the chloroform guest.
The structures of (I) and (II) are best described comparatively, and hence the values in brackets refer to the equivalent parameter in (II) to that stated for (I). The angles about the meso-C atoms [C1, C8, C17 and C24 for (I), and C7, C14, C21 and C28 for (II)], given in Tables 1 and 2, are reasonably close to ideal tetrahedral geometry, indicating a strain-free macrocycle. The upper rim of calixarene (I) forms a cavity with separations between meso-C atoms of 5.067 (2), 5.075 (2), 5.079 (2) and 5.070 (2) Å [5.066 (3), 5.090 (3), 5.067 (3) and 5.099 (3) Å] and cross-ring distances between meso-C atoms of 7.312 (2) and 7.031 (2) Å [7.352 (3) and 7.008 (3) Å]. The asymmetry of the macrocycle is caused by the lower-rim substituents, which form a number of intramolecular hydrogen bonds with each other. In addition, the angles of the aromatic rings in the calixarene with respect to the mean plane of the macrocyle (defined by the meso-C atoms) are 71.70 (4) and 68.46 (3)° [73.68 (7) and 68.42 (6)°] for the alkyl ester functionalized rings, whilst those for the hydroxy-substituted rings are 42.35 (4) and 37.86 (5)° [45.52 (7) and 49.17 (6)°]. Thus, the hydroxy-substituted rings are allowed to lie more in the plane of the macrocycle due to their relatively small functional groups on the lower rim and the intramolecular interactions in which they are involved. The separation of the terminal methyl groups of the ester function is 6.475 (2) Å [7.141 (3) Å], reflecting the dilation of the lower rim substituents in calixarene (II) in order to accommodate the chloroform moiety.
Pertinent hydrogen-bonding parameters are given in Tables 2 and 4. The pendant ester groups are locked in position by strong hydrogen bonding between the hydroxy substituent and the oxy-linkage between the calixarene and the ester and these are of comparable strength in (I) and (II). There is a further interaction between the carbonyl group of the ester and the hydroxy substituent, making it a bifurcated donor. This interaction is weaker in (I) compared with (II) as the arms are allowed to adopt the most favourable conformation, as opposed to those of (II) which interact with the chloroform guest molecule. Non-classical interactions, presumably electrostatic, occur in (II) between the guest and host [D···A = Cl2···O5 = 3.316 (2) Å, Cl1···O8 = 3.349 (2) Å, C37···O4 = 3.221 (3) Å and C37···O5 = 3.075 (3) Å].