Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010401323X/hj1009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010401323X/hj1009Isup2.hkl |
CCDC reference: 245931
Compound (I) was prepared as described by Collins et al. (1991) and was recrystallized from DMF/H2O (Ratio?).
H atoms were placed in geometric positions, with O—H distances of 0.84 Å and C—H distances in the range 0.95–0.99 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C,O). Please check added text.
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C48H60O8·3C3H7NO | F(000) = 2128 |
Mr = 984.25 | Dx = 1.200 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 7352 reflections |
a = 11.3624 (3) Å | θ = 5.0–131.9° |
b = 35.224 (1) Å | µ = 0.66 mm−1 |
c = 13.7180 (4) Å | T = 100 K |
β = 96.991 (2)° | Needle, colorless |
V = 5449.6 (3) Å3 | 0.30 × 0.11 × 0.07 mm |
Z = 4 |
Bruker SMART 1000 CCD area-detector diffractometer | 9142 independent reflections |
Radiation source: fine-focus sealed tube | 6845 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 66.2°, θmin = 2.5° |
Absorption correction: integration face-indexing of crystal Reference | h = −12→13 |
Tmin = 0.862, Tmax = 0.961 | k = −41→41 |
25773 measured reflections | l = −15→16 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3 |
9142 reflections | (Δ/σ)max = 0.012 |
662 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C48H60O8·3C3H7NO | V = 5449.6 (3) Å3 |
Mr = 984.25 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 11.3624 (3) Å | µ = 0.66 mm−1 |
b = 35.224 (1) Å | T = 100 K |
c = 13.7180 (4) Å | 0.30 × 0.11 × 0.07 mm |
β = 96.991 (2)° |
Bruker SMART 1000 CCD area-detector diffractometer | 9142 independent reflections |
Absorption correction: integration face-indexing of crystal Reference | 6845 reflections with I > 2σ(I) |
Tmin = 0.862, Tmax = 0.961 | Rint = 0.056 |
25773 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.25 e Å−3 |
9142 reflections | Δρmin = −0.28 e Å−3 |
662 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. |
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. Full matrix refinement of F2 against all reflections until complete convergence was attained. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.31598 (10) | 0.12410 (3) | 0.94587 (9) | 0.0178 (3) | |
O2 | 0.34102 (11) | 0.06257 (4) | 0.82534 (9) | 0.0245 (3) | |
H2 | 0.3183 | 0.0805 | 0.8587 | 0.029* | |
O3 | 0.59093 (11) | 0.03554 (3) | 0.89186 (9) | 0.0233 (3) | |
O4 | 0.56290 (11) | 0.10848 (3) | 0.96288 (10) | 0.0229 (3) | |
H4 | 0.5848 | 0.0871 | 0.9449 | 0.027* | |
O5 | 0.10168 (12) | 0.09340 (4) | 0.98019 (10) | 0.0289 (3) | |
O6 | 0.10918 (12) | 0.12491 (4) | 1.12268 (10) | 0.0284 (3) | |
H6 | 0.0480 | 0.1123 | 1.1293 | 0.034* | |
O7 | 0.70029 (14) | −0.05300 (4) | 0.86587 (12) | 0.0405 (4) | |
O8 | 0.50933 (13) | −0.04164 (4) | 0.88456 (11) | 0.0357 (4) | |
H8 | 0.4973 | −0.0620 | 0.8530 | 0.043* | |
C1 | 0.24570 (15) | 0.15702 (5) | 0.79782 (13) | 0.0172 (4) | |
C2 | 0.16915 (15) | 0.12320 (5) | 0.76170 (13) | 0.0189 (4) | |
H2A | 0.0930 | 0.1325 | 0.7272 | 0.023* | |
H2B | 0.1515 | 0.1080 | 0.8188 | 0.023* | |
C3 | 0.22973 (15) | 0.09805 (5) | 0.69245 (13) | 0.0189 (4) | |
C4 | 0.20678 (16) | 0.10365 (5) | 0.59103 (13) | 0.0214 (4) | |
H4A | 0.1526 | 0.1230 | 0.5673 | 0.026* | |
C5 | 0.25977 (16) | 0.08206 (6) | 0.52325 (14) | 0.0241 (4) | |
C6 | 0.33886 (16) | 0.05401 (6) | 0.56190 (14) | 0.0246 (4) | |
H6A | 0.3748 | 0.0383 | 0.5176 | 0.030* | |
C7 | 0.36754 (16) | 0.04798 (5) | 0.66177 (14) | 0.0210 (4) | |
C8 | 0.46173 (16) | 0.01909 (5) | 0.69972 (15) | 0.0241 (4) | |
H8A | 0.4620 | −0.0020 | 0.6521 | 0.029* | |
H8B | 0.4429 | 0.0084 | 0.7628 | 0.029* | |
C9 | 0.58372 (16) | 0.03755 (5) | 0.71473 (15) | 0.0226 (4) | |
C10 | 0.63838 (16) | 0.04808 (5) | 0.63327 (15) | 0.0249 (4) | |
H10 | 0.6011 | 0.0414 | 0.5698 | 0.030* | |
C11 | 0.74489 (17) | 0.06790 (6) | 0.64050 (15) | 0.0256 (4) | |
C12 | 0.79476 (16) | 0.07819 (5) | 0.73512 (15) | 0.0238 (4) | |
H12 | 0.8662 | 0.0925 | 0.7423 | 0.029* | |
C13 | 0.74451 (16) | 0.06844 (5) | 0.81873 (14) | 0.0211 (4) | |
C14 | 0.79754 (16) | 0.08400 (5) | 0.91776 (14) | 0.0214 (4) | |
H14A | 0.8850 | 0.0820 | 0.9233 | 0.026* | |
H14B | 0.7702 | 0.0684 | 0.9706 | 0.026* | |
C15 | 0.76307 (15) | 0.12517 (5) | 0.93182 (13) | 0.0189 (4) | |
C16 | 0.84545 (16) | 0.15416 (5) | 0.92653 (13) | 0.0198 (4) | |
H16 | 0.9225 | 0.1477 | 0.9118 | 0.024* | |
C17 | 0.81946 (15) | 0.19216 (5) | 0.94192 (13) | 0.0182 (4) | |
C18 | 0.70517 (15) | 0.20050 (5) | 0.96389 (13) | 0.0178 (4) | |
H18 | 0.6849 | 0.2262 | 0.9747 | 0.021* | |
C19 | 0.62031 (15) | 0.17253 (5) | 0.97038 (13) | 0.0169 (4) | |
C20 | 0.49912 (15) | 0.18234 (5) | 0.99909 (13) | 0.0169 (4) | |
H20A | 0.5040 | 0.2071 | 1.0336 | 0.020* | |
H20B | 0.4764 | 0.1629 | 1.0455 | 0.020* | |
C21 | 0.40318 (15) | 0.18457 (5) | 0.91173 (13) | 0.0159 (4) | |
C22 | 0.39801 (15) | 0.21723 (5) | 0.85309 (13) | 0.0182 (4) | |
H22 | 0.4518 | 0.2374 | 0.8711 | 0.022* | |
C23 | 0.31639 (15) | 0.22103 (5) | 0.76922 (13) | 0.0185 (4) | |
C24 | 0.24388 (15) | 0.18981 (5) | 0.74201 (13) | 0.0187 (4) | |
H24 | 0.1912 | 0.1911 | 0.6828 | 0.022* | |
C25 | 0.32193 (15) | 0.15580 (5) | 0.88565 (13) | 0.0165 (4) | |
C26 | 0.64955 (15) | 0.13468 (5) | 0.95281 (13) | 0.0179 (4) | |
C27 | 0.64114 (16) | 0.04650 (5) | 0.80746 (14) | 0.0210 (4) | |
C28 | 0.31214 (15) | 0.07023 (5) | 0.72758 (14) | 0.0203 (4) | |
C29 | 0.30050 (16) | 0.25810 (5) | 0.71075 (14) | 0.0226 (4) | |
C30 | 0.29568 (17) | 0.24998 (6) | 0.59996 (14) | 0.0274 (5) | |
H30A | 0.2846 | 0.2739 | 0.5633 | 0.041* | |
H30B | 0.2293 | 0.2329 | 0.5793 | 0.041* | |
H30C | 0.3701 | 0.2380 | 0.5868 | 0.041* | |
C31 | 0.40149 (19) | 0.28580 (6) | 0.74001 (16) | 0.0325 (5) | |
H31A | 0.4052 | 0.2916 | 0.8102 | 0.049* | |
H31B | 0.3877 | 0.3093 | 0.7019 | 0.049* | |
H31C | 0.4766 | 0.2744 | 0.7267 | 0.049* | |
C32 | 0.18311 (19) | 0.27648 (6) | 0.73175 (16) | 0.0350 (5) | |
H32A | 0.1862 | 0.2815 | 0.8023 | 0.053* | |
H32B | 0.1172 | 0.2592 | 0.7110 | 0.053* | |
H32C | 0.1713 | 0.3004 | 0.6953 | 0.053* | |
C33 | 0.91014 (16) | 0.22424 (5) | 0.93626 (14) | 0.0224 (4) | |
C34 | 0.8755 (2) | 0.24774 (7) | 0.84402 (19) | 0.0500 (7) | |
H34A | 0.9332 | 0.2682 | 0.8406 | 0.075* | |
H34B | 0.7965 | 0.2587 | 0.8462 | 0.075* | |
H34C | 0.8744 | 0.2315 | 0.7860 | 0.075* | |
C35 | 0.9123 (2) | 0.25015 (7) | 1.0259 (2) | 0.0532 (7) | |
H35A | 0.9314 | 0.2351 | 1.0859 | 0.080* | |
H35B | 0.8344 | 0.2620 | 1.0263 | 0.080* | |
H35C | 0.9725 | 0.2699 | 1.0229 | 0.080* | |
C36 | 1.03490 (17) | 0.20917 (6) | 0.93302 (17) | 0.0336 (5) | |
H36A | 1.0365 | 0.1934 | 0.8744 | 0.050* | |
H36B | 1.0588 | 0.1939 | 0.9918 | 0.050* | |
H36C | 1.0899 | 0.2305 | 0.9308 | 0.050* | |
C37 | 0.80728 (18) | 0.07844 (6) | 0.55114 (15) | 0.0307 (5) | |
C38 | 0.84109 (19) | 0.12065 (6) | 0.55457 (16) | 0.0343 (5) | |
H38A | 0.8806 | 0.1270 | 0.4970 | 0.051* | |
H38B | 0.8949 | 0.1258 | 0.6145 | 0.051* | |
H38C | 0.7694 | 0.1361 | 0.5544 | 0.051* | |
C39 | 0.7291 (2) | 0.07112 (8) | 0.45466 (16) | 0.0495 (7) | |
H39A | 0.6531 | 0.0842 | 0.4553 | 0.074* | |
H39B | 0.7151 | 0.0438 | 0.4466 | 0.074* | |
H39C | 0.7687 | 0.0806 | 0.4000 | 0.074* | |
C40 | 0.9205 (2) | 0.05453 (7) | 0.55418 (19) | 0.0445 (6) | |
H40A | 0.8995 | 0.0276 | 0.5498 | 0.067* | |
H40B | 0.9714 | 0.0593 | 0.6159 | 0.067* | |
H40C | 0.9630 | 0.0615 | 0.4988 | 0.067* | |
C41 | 0.23573 (18) | 0.08807 (6) | 0.41193 (14) | 0.0297 (5) | |
C42 | 0.18277 (19) | 0.05193 (6) | 0.36245 (15) | 0.0357 (5) | |
H42A | 0.1064 | 0.0465 | 0.3859 | 0.054* | |
H42B | 0.2371 | 0.0306 | 0.3787 | 0.054* | |
H42C | 0.1709 | 0.0556 | 0.2911 | 0.054* | |
C43 | 0.1498 (2) | 0.12097 (7) | 0.38517 (16) | 0.0458 (6) | |
H43A | 0.1376 | 0.1241 | 0.3137 | 0.069* | |
H43B | 0.1832 | 0.1444 | 0.4156 | 0.069* | |
H43C | 0.0738 | 0.1155 | 0.4091 | 0.069* | |
C44 | 0.3528 (2) | 0.09693 (8) | 0.37082 (16) | 0.0441 (6) | |
H44A | 0.3375 | 0.1002 | 0.2994 | 0.066* | |
H44B | 0.4086 | 0.0759 | 0.3861 | 0.066* | |
H44C | 0.3870 | 0.1203 | 0.4007 | 0.066* | |
C45 | 0.65036 (18) | 0.00402 (5) | 0.94496 (15) | 0.0288 (5) | |
H45A | 0.6251 | 0.0028 | 1.0115 | 0.035* | |
H45B | 0.7370 | 0.0085 | 0.9525 | 0.035* | |
C46 | 0.62358 (18) | −0.03334 (6) | 0.89346 (15) | 0.0282 (5) | |
C47 | 0.27178 (16) | 0.13161 (5) | 1.03710 (13) | 0.0201 (4) | |
H47A | 0.2667 | 0.1594 | 1.0464 | 0.024* | |
H47B | 0.3281 | 0.1213 | 1.0915 | 0.024* | |
C48 | 0.15161 (16) | 0.11430 (5) | 1.04161 (14) | 0.0211 (4) | |
O9 | −0.06440 (13) | 0.08202 (4) | 1.15967 (11) | 0.0348 (4) | |
O10 | 0.57827 (13) | 0.21186 (4) | 0.49546 (10) | 0.0376 (4) | |
O11 | 0.44046 (14) | −0.10180 (4) | 0.78636 (11) | 0.0404 (4) | |
N1 | −0.08627 (15) | 0.01792 (5) | 1.17031 (13) | 0.0294 (4) | |
N2 | 0.56878 (13) | 0.17466 (4) | 0.63073 (12) | 0.0240 (4) | |
N3 | 0.29204 (15) | −0.14556 (5) | 0.76332 (12) | 0.0294 (4) | |
C49 | −0.03327 (18) | 0.04883 (6) | 1.14392 (16) | 0.0309 (5) | |
H49 | 0.0342 | 0.0456 | 1.1101 | 0.037* | |
C50 | −0.1865 (2) | 0.02034 (7) | 1.2258 (2) | 0.0554 (7) | |
H50A | −0.2000 | 0.0469 | 1.2424 | 0.083* | |
H50B | −0.1702 | 0.0055 | 1.2863 | 0.083* | |
H50C | −0.2573 | 0.0103 | 1.1863 | 0.083* | |
C51 | −0.0476 (3) | −0.01966 (7) | 1.1479 (2) | 0.0660 (9) | |
H51A | 0.0179 | −0.0179 | 1.1077 | 0.099* | |
H51B | −0.1136 | −0.0336 | 1.1116 | 0.099* | |
H51C | −0.0206 | −0.0331 | 1.2091 | 0.099* | |
C52 | 0.53787 (18) | 0.18500 (6) | 0.53816 (16) | 0.0296 (5) | |
H52 | 0.4786 | 0.1702 | 0.5011 | 0.036* | |
C53 | 0.51504 (18) | 0.14287 (6) | 0.67597 (16) | 0.0313 (5) | |
H53A | 0.4573 | 0.1305 | 0.6273 | 0.047* | |
H53B | 0.4749 | 0.1520 | 0.7307 | 0.047* | |
H53C | 0.5767 | 0.1246 | 0.7005 | 0.047* | |
C54 | 0.65705 (19) | 0.19631 (7) | 0.69364 (16) | 0.0397 (6) | |
H54A | 0.6878 | 0.2168 | 0.6555 | 0.060* | |
H54B | 0.7223 | 0.1795 | 0.7193 | 0.060* | |
H54C | 0.6205 | 0.2072 | 0.7484 | 0.060* | |
C55 | 0.34690 (19) | −0.11609 (6) | 0.80825 (15) | 0.0308 (5) | |
H55 | 0.3123 | −0.1050 | 0.8611 | 0.037* | |
C56 | 0.3373 (2) | −0.16370 (7) | 0.68058 (16) | 0.0390 (6) | |
H56A | 0.4070 | −0.1498 | 0.6642 | 0.058* | |
H56B | 0.2758 | −0.1636 | 0.6239 | 0.058* | |
H56C | 0.3595 | −0.1900 | 0.6978 | 0.058* | |
C57 | 0.18544 (19) | −0.16116 (7) | 0.79615 (16) | 0.0365 (5) | |
H57A | 0.1653 | −0.1467 | 0.8528 | 0.055* | |
H57B | 0.1991 | −0.1878 | 0.8150 | 0.055* | |
H57C | 0.1199 | −0.1596 | 0.7428 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0180 (7) | 0.0161 (6) | 0.0200 (7) | −0.0006 (5) | 0.0053 (5) | 0.0024 (5) |
O2 | 0.0273 (7) | 0.0230 (7) | 0.0228 (7) | 0.0045 (6) | 0.0014 (6) | −0.0013 (6) |
O3 | 0.0223 (7) | 0.0185 (7) | 0.0298 (8) | 0.0011 (6) | 0.0059 (5) | 0.0007 (6) |
O4 | 0.0183 (7) | 0.0152 (6) | 0.0356 (8) | −0.0017 (5) | 0.0055 (5) | −0.0029 (6) |
O5 | 0.0250 (8) | 0.0349 (8) | 0.0275 (8) | −0.0104 (6) | 0.0057 (6) | −0.0041 (7) |
O6 | 0.0268 (8) | 0.0313 (8) | 0.0296 (8) | −0.0086 (6) | 0.0134 (6) | −0.0038 (7) |
O7 | 0.0413 (9) | 0.0309 (8) | 0.0507 (10) | 0.0079 (7) | 0.0118 (8) | −0.0050 (7) |
O8 | 0.0347 (9) | 0.0268 (8) | 0.0456 (10) | −0.0047 (7) | 0.0047 (7) | −0.0066 (7) |
C1 | 0.0114 (9) | 0.0202 (10) | 0.0210 (10) | 0.0015 (7) | 0.0065 (7) | −0.0014 (8) |
C2 | 0.0133 (9) | 0.0221 (10) | 0.0211 (10) | −0.0012 (8) | 0.0019 (7) | 0.0012 (8) |
C3 | 0.0136 (9) | 0.0203 (9) | 0.0230 (10) | −0.0063 (8) | 0.0030 (7) | −0.0017 (8) |
C4 | 0.0171 (10) | 0.0235 (10) | 0.0234 (10) | −0.0043 (8) | 0.0013 (7) | −0.0009 (9) |
C5 | 0.0201 (10) | 0.0299 (11) | 0.0227 (11) | −0.0094 (8) | 0.0038 (8) | −0.0048 (9) |
C6 | 0.0184 (10) | 0.0265 (11) | 0.0301 (11) | −0.0056 (8) | 0.0074 (8) | −0.0092 (9) |
C7 | 0.0145 (9) | 0.0205 (10) | 0.0281 (11) | −0.0055 (8) | 0.0028 (7) | −0.0024 (9) |
C8 | 0.0184 (10) | 0.0205 (10) | 0.0337 (11) | −0.0032 (8) | 0.0050 (8) | −0.0062 (9) |
C9 | 0.0171 (10) | 0.0159 (9) | 0.0353 (12) | −0.0002 (8) | 0.0058 (8) | −0.0056 (9) |
C10 | 0.0201 (10) | 0.0240 (10) | 0.0301 (11) | −0.0006 (8) | 0.0009 (8) | −0.0074 (9) |
C11 | 0.0187 (10) | 0.0252 (10) | 0.0336 (12) | 0.0007 (8) | 0.0069 (8) | −0.0054 (9) |
C12 | 0.0149 (9) | 0.0206 (10) | 0.0357 (12) | −0.0007 (8) | 0.0029 (8) | −0.0058 (9) |
C13 | 0.0167 (10) | 0.0156 (9) | 0.0310 (11) | 0.0035 (7) | 0.0031 (8) | −0.0016 (8) |
C14 | 0.0144 (9) | 0.0184 (9) | 0.0309 (11) | 0.0006 (8) | 0.0013 (8) | −0.0019 (8) |
C15 | 0.0169 (9) | 0.0193 (9) | 0.0200 (10) | 0.0027 (8) | 0.0003 (7) | −0.0012 (8) |
C16 | 0.0134 (9) | 0.0219 (10) | 0.0243 (10) | 0.0009 (8) | 0.0031 (7) | −0.0006 (8) |
C17 | 0.0150 (9) | 0.0196 (9) | 0.0197 (10) | −0.0011 (8) | 0.0010 (7) | 0.0005 (8) |
C18 | 0.0165 (9) | 0.0156 (9) | 0.0208 (10) | 0.0016 (7) | 0.0008 (7) | −0.0007 (8) |
C19 | 0.0139 (9) | 0.0187 (9) | 0.0178 (10) | 0.0006 (7) | 0.0006 (7) | 0.0003 (8) |
C20 | 0.0147 (9) | 0.0168 (9) | 0.0194 (10) | 0.0001 (7) | 0.0033 (7) | −0.0007 (8) |
C21 | 0.0120 (9) | 0.0177 (9) | 0.0189 (10) | 0.0024 (7) | 0.0059 (7) | −0.0017 (8) |
C22 | 0.0151 (9) | 0.0181 (9) | 0.0222 (10) | −0.0020 (8) | 0.0061 (7) | −0.0012 (8) |
C23 | 0.0170 (9) | 0.0192 (9) | 0.0203 (10) | 0.0023 (8) | 0.0063 (7) | 0.0013 (8) |
C24 | 0.0151 (9) | 0.0226 (10) | 0.0183 (10) | 0.0012 (8) | 0.0018 (7) | 0.0011 (8) |
C25 | 0.0138 (9) | 0.0158 (9) | 0.0210 (10) | 0.0017 (7) | 0.0064 (7) | 0.0014 (8) |
C26 | 0.0138 (9) | 0.0193 (9) | 0.0202 (10) | −0.0021 (7) | 0.0005 (7) | 0.0004 (8) |
C27 | 0.0173 (10) | 0.0150 (9) | 0.0309 (11) | 0.0036 (7) | 0.0041 (8) | −0.0024 (8) |
C28 | 0.0156 (9) | 0.0191 (10) | 0.0261 (11) | −0.0056 (8) | 0.0027 (7) | −0.0010 (8) |
C29 | 0.0234 (10) | 0.0195 (10) | 0.0251 (11) | 0.0006 (8) | 0.0037 (8) | 0.0053 (8) |
C30 | 0.0278 (11) | 0.0277 (11) | 0.0265 (11) | −0.0014 (9) | 0.0021 (8) | 0.0070 (9) |
C31 | 0.0410 (13) | 0.0245 (11) | 0.0307 (12) | −0.0072 (10) | −0.0010 (9) | 0.0079 (10) |
C32 | 0.0382 (13) | 0.0273 (11) | 0.0420 (13) | 0.0114 (10) | 0.0149 (10) | 0.0110 (10) |
C33 | 0.0158 (9) | 0.0193 (10) | 0.0325 (11) | −0.0028 (8) | 0.0044 (8) | −0.0016 (9) |
C34 | 0.0294 (13) | 0.0432 (14) | 0.0735 (18) | −0.0150 (11) | −0.0091 (12) | 0.0303 (13) |
C35 | 0.0367 (14) | 0.0505 (16) | 0.0766 (19) | −0.0250 (12) | 0.0247 (13) | −0.0334 (14) |
C36 | 0.0184 (11) | 0.0277 (11) | 0.0556 (15) | −0.0039 (9) | 0.0085 (9) | 0.0016 (11) |
C37 | 0.0232 (11) | 0.0369 (12) | 0.0334 (12) | −0.0056 (9) | 0.0088 (9) | −0.0054 (10) |
C38 | 0.0291 (12) | 0.0412 (13) | 0.0333 (12) | −0.0011 (10) | 0.0065 (9) | 0.0033 (11) |
C39 | 0.0484 (15) | 0.0701 (18) | 0.0319 (13) | −0.0218 (13) | 0.0135 (11) | −0.0090 (13) |
C40 | 0.0367 (14) | 0.0433 (14) | 0.0591 (16) | 0.0010 (11) | 0.0284 (12) | −0.0028 (12) |
C41 | 0.0281 (11) | 0.0396 (12) | 0.0219 (11) | −0.0045 (10) | 0.0053 (8) | −0.0031 (10) |
C42 | 0.0295 (12) | 0.0510 (14) | 0.0264 (12) | −0.0066 (10) | 0.0025 (9) | −0.0074 (11) |
C43 | 0.0652 (17) | 0.0515 (15) | 0.0203 (12) | 0.0062 (13) | 0.0031 (11) | 0.0033 (11) |
C44 | 0.0436 (14) | 0.0641 (17) | 0.0261 (12) | −0.0205 (12) | 0.0108 (10) | −0.0051 (12) |
C45 | 0.0281 (11) | 0.0244 (11) | 0.0333 (12) | 0.0013 (9) | 0.0016 (9) | 0.0013 (9) |
C46 | 0.0311 (12) | 0.0248 (11) | 0.0289 (11) | 0.0023 (9) | 0.0043 (9) | 0.0039 (9) |
C47 | 0.0205 (10) | 0.0199 (10) | 0.0205 (10) | −0.0016 (8) | 0.0048 (7) | 0.0006 (8) |
C48 | 0.0215 (10) | 0.0196 (10) | 0.0221 (10) | 0.0004 (8) | 0.0031 (8) | 0.0024 (9) |
O9 | 0.0362 (9) | 0.0268 (8) | 0.0437 (9) | −0.0061 (7) | 0.0142 (7) | −0.0023 (7) |
O10 | 0.0486 (10) | 0.0306 (8) | 0.0343 (9) | −0.0028 (7) | 0.0078 (7) | 0.0065 (7) |
O11 | 0.0421 (10) | 0.0398 (9) | 0.0402 (9) | −0.0127 (8) | 0.0087 (7) | −0.0061 (8) |
N1 | 0.0281 (9) | 0.0241 (9) | 0.0374 (10) | −0.0019 (8) | 0.0094 (7) | −0.0004 (8) |
N2 | 0.0203 (8) | 0.0245 (9) | 0.0275 (9) | −0.0044 (7) | 0.0037 (7) | 0.0007 (7) |
N3 | 0.0320 (10) | 0.0280 (9) | 0.0280 (10) | −0.0033 (8) | 0.0031 (7) | −0.0016 (8) |
C49 | 0.0254 (11) | 0.0328 (12) | 0.0353 (13) | −0.0006 (9) | 0.0076 (9) | 0.0007 (10) |
C50 | 0.0590 (18) | 0.0344 (14) | 0.081 (2) | −0.0094 (12) | 0.0417 (15) | −0.0019 (13) |
C51 | 0.078 (2) | 0.0292 (14) | 0.099 (2) | 0.0151 (14) | 0.0421 (18) | 0.0074 (15) |
C52 | 0.0277 (11) | 0.0287 (11) | 0.0320 (12) | 0.0014 (9) | 0.0017 (9) | −0.0029 (10) |
C53 | 0.0298 (12) | 0.0287 (11) | 0.0373 (13) | −0.0014 (9) | 0.0111 (9) | 0.0039 (10) |
C54 | 0.0359 (13) | 0.0468 (14) | 0.0357 (13) | −0.0159 (11) | 0.0019 (10) | −0.0045 (11) |
C55 | 0.0358 (13) | 0.0297 (12) | 0.0264 (11) | −0.0023 (10) | 0.0022 (9) | 0.0012 (10) |
C56 | 0.0411 (14) | 0.0369 (13) | 0.0393 (14) | 0.0002 (11) | 0.0063 (10) | −0.0098 (11) |
C57 | 0.0340 (13) | 0.0390 (13) | 0.0367 (13) | −0.0042 (10) | 0.0042 (10) | −0.0042 (11) |
O1—C25 | 1.396 (2) | C32—H32C | 0.9800 |
O1—C47 | 1.429 (2) | C33—C36 | 1.519 (3) |
O2—C28 | 1.368 (2) | C33—C34 | 1.523 (3) |
O2—H2 | 0.8400 | C33—C35 | 1.529 (3) |
O3—C27 | 1.406 (2) | C34—H34A | 0.9800 |
O3—C45 | 1.449 (2) | C34—H34B | 0.9800 |
O4—C26 | 1.369 (2) | C34—H34C | 0.9800 |
O4—H4 | 0.8400 | C35—H35A | 0.9800 |
O5—C48 | 1.207 (2) | C35—H35B | 0.9800 |
O6—C48 | 1.319 (2) | C35—H35C | 0.9800 |
O6—H6 | 0.8400 | C36—H36A | 0.9800 |
O7—C46 | 1.210 (2) | C36—H36B | 0.9800 |
O8—C46 | 1.322 (2) | C36—H36C | 0.9800 |
O8—H8 | 0.8400 | C37—C39 | 1.524 (3) |
C1—C24 | 1.384 (2) | C37—C38 | 1.535 (3) |
C1—C25 | 1.396 (2) | C37—C40 | 1.534 (3) |
C1—C2 | 1.522 (2) | C38—H38A | 0.9800 |
C2—C3 | 1.523 (2) | C38—H38B | 0.9800 |
C2—H2A | 0.9900 | C38—H38C | 0.9800 |
C2—H2B | 0.9900 | C39—H39A | 0.9800 |
C3—C4 | 1.398 (3) | C39—H39B | 0.9800 |
C3—C28 | 1.400 (3) | C39—H39C | 0.9800 |
C4—C5 | 1.393 (3) | C40—H40A | 0.9800 |
C4—H4A | 0.9500 | C40—H40B | 0.9800 |
C5—C6 | 1.396 (3) | C40—H40C | 0.9800 |
C5—C41 | 1.533 (3) | C41—C42 | 1.531 (3) |
C6—C7 | 1.386 (3) | C41—C43 | 1.531 (3) |
C6—H6A | 0.9500 | C41—C44 | 1.539 (3) |
C7—C28 | 1.401 (3) | C42—H42A | 0.9800 |
C7—C8 | 1.522 (3) | C42—H42B | 0.9800 |
C8—C9 | 1.522 (2) | C42—H42C | 0.9800 |
C8—H8A | 0.9900 | C43—H43A | 0.9800 |
C8—H8B | 0.9900 | C43—H43B | 0.9800 |
C9—C10 | 1.393 (3) | C43—H43C | 0.9800 |
C9—C27 | 1.393 (3) | C44—H44A | 0.9800 |
C10—C11 | 1.390 (3) | C44—H44B | 0.9800 |
C10—H10 | 0.9500 | C44—H44C | 0.9800 |
C11—C12 | 1.399 (3) | C45—C46 | 1.507 (3) |
C11—C37 | 1.535 (3) | C45—H45A | 0.9900 |
C12—C13 | 1.385 (3) | C45—H45B | 0.9900 |
C12—H12 | 0.9500 | C47—C48 | 1.504 (3) |
C13—C27 | 1.399 (3) | C47—H47A | 0.9900 |
C13—C14 | 1.520 (3) | C47—H47B | 0.9900 |
C14—C15 | 1.520 (2) | O9—C49 | 1.248 (2) |
C14—H14A | 0.9900 | O10—C52 | 1.230 (2) |
C14—H14B | 0.9900 | O11—C55 | 1.246 (2) |
C15—C16 | 1.393 (3) | N1—C49 | 1.316 (3) |
C15—C26 | 1.396 (2) | N1—C51 | 1.440 (3) |
C16—C17 | 1.392 (2) | N1—C50 | 1.447 (3) |
C16—H16 | 0.9500 | N2—C52 | 1.327 (3) |
C17—C18 | 1.400 (2) | N2—C53 | 1.451 (2) |
C17—C33 | 1.538 (2) | N2—C54 | 1.457 (3) |
C18—C19 | 1.389 (2) | N3—C55 | 1.324 (3) |
C18—H18 | 0.9500 | N3—C57 | 1.451 (3) |
C19—C26 | 1.402 (2) | N3—C56 | 1.450 (3) |
C19—C20 | 1.517 (2) | C49—H49 | 0.9500 |
C20—C21 | 1.521 (2) | C50—H50A | 0.9800 |
C20—H20A | 0.9900 | C50—H50B | 0.9800 |
C20—H20B | 0.9900 | C50—H50C | 0.9800 |
C21—C25 | 1.388 (2) | C51—H51A | 0.9800 |
C21—C22 | 1.401 (2) | C51—H51B | 0.9800 |
C22—C23 | 1.394 (2) | C51—H51C | 0.9800 |
C22—H22 | 0.9500 | C52—H52 | 0.9500 |
C23—C24 | 1.397 (2) | C53—H53A | 0.9800 |
C23—C29 | 1.531 (2) | C53—H53B | 0.9800 |
C24—H24 | 0.9500 | C53—H53C | 0.9800 |
C29—C31 | 1.522 (3) | C54—H54A | 0.9800 |
C29—C30 | 1.541 (3) | C54—H54B | 0.9800 |
C29—C32 | 1.541 (3) | C54—H54C | 0.9800 |
C30—H30A | 0.9800 | C55—H55 | 0.9500 |
C30—H30B | 0.9800 | C56—H56A | 0.9800 |
C30—H30C | 0.9800 | C56—H56B | 0.9800 |
C31—H31A | 0.9800 | C56—H56C | 0.9800 |
C31—H31B | 0.9800 | C57—H57A | 0.9800 |
C31—H31C | 0.9800 | C57—H57B | 0.9800 |
C32—H32A | 0.9800 | C57—H57C | 0.9800 |
C32—H32B | 0.9800 | ||
C25—O1—C47 | 114.70 (13) | C33—C34—H34C | 109.5 |
C28—O2—H2 | 109.5 | H34A—C34—H34C | 109.5 |
C27—O3—C45 | 114.42 (14) | H34B—C34—H34C | 109.5 |
C26—O4—H4 | 109.5 | C33—C35—H35A | 109.5 |
C48—O6—H6 | 109.5 | C33—C35—H35B | 109.5 |
C46—O8—H8 | 109.5 | H35A—C35—H35B | 109.5 |
C24—C1—C25 | 117.95 (16) | C33—C35—H35C | 109.5 |
C24—C1—C2 | 120.24 (16) | H35A—C35—H35C | 109.5 |
C25—C1—C2 | 121.79 (16) | H35B—C35—H35C | 109.5 |
C1—C2—C3 | 112.00 (14) | C33—C36—H36A | 109.5 |
C1—C2—H2A | 109.2 | C33—C36—H36B | 109.5 |
C3—C2—H2A | 109.2 | H36A—C36—H36B | 109.5 |
C1—C2—H2B | 109.2 | C33—C36—H36C | 109.5 |
C3—C2—H2B | 109.2 | H36A—C36—H36C | 109.5 |
H2A—C2—H2B | 107.9 | H36B—C36—H36C | 109.5 |
C4—C3—C28 | 118.52 (17) | C39—C37—C38 | 107.94 (19) |
C4—C3—C2 | 119.65 (16) | C39—C37—C40 | 109.23 (19) |
C28—C3—C2 | 121.77 (16) | C38—C37—C40 | 108.96 (17) |
C5—C4—C3 | 122.92 (18) | C39—C37—C11 | 112.07 (17) |
C5—C4—H4A | 118.5 | C38—C37—C11 | 110.38 (17) |
C3—C4—H4A | 118.5 | C40—C37—C11 | 108.23 (18) |
C4—C5—C6 | 116.32 (18) | C37—C38—H38A | 109.5 |
C4—C5—C41 | 123.39 (18) | C37—C38—H38B | 109.5 |
C6—C5—C41 | 120.29 (17) | H38A—C38—H38B | 109.5 |
C7—C6—C5 | 123.17 (18) | C37—C38—H38C | 109.5 |
C7—C6—H6A | 118.4 | H38A—C38—H38C | 109.5 |
C5—C6—H6A | 118.4 | H38B—C38—H38C | 109.5 |
C6—C7—C28 | 118.77 (17) | C37—C39—H39A | 109.5 |
C6—C7—C8 | 120.78 (17) | C37—C39—H39B | 109.5 |
C28—C7—C8 | 120.39 (17) | H39A—C39—H39B | 109.5 |
C7—C8—C9 | 110.57 (15) | C37—C39—H39C | 109.5 |
C7—C8—H8A | 109.5 | H39A—C39—H39C | 109.5 |
C9—C8—H8A | 109.5 | H39B—C39—H39C | 109.5 |
C7—C8—H8B | 109.5 | C37—C40—H40A | 109.5 |
C9—C8—H8B | 109.5 | C37—C40—H40B | 109.5 |
H8A—C8—H8B | 108.1 | H40A—C40—H40B | 109.5 |
C10—C9—C27 | 117.85 (17) | C37—C40—H40C | 109.5 |
C10—C9—C8 | 119.52 (17) | H40A—C40—H40C | 109.5 |
C27—C9—C8 | 122.52 (17) | H40B—C40—H40C | 109.5 |
C11—C10—C9 | 123.07 (19) | C42—C41—C43 | 108.57 (18) |
C11—C10—H10 | 118.5 | C42—C41—C5 | 109.86 (17) |
C9—C10—H10 | 118.5 | C43—C41—C5 | 111.99 (17) |
C10—C11—C12 | 116.55 (18) | C42—C41—C44 | 108.48 (17) |
C10—C11—C37 | 123.18 (18) | C43—C41—C44 | 108.23 (19) |
C12—C11—C37 | 120.27 (17) | C5—C41—C44 | 109.63 (17) |
C13—C12—C11 | 122.86 (18) | C41—C42—H42A | 109.5 |
C13—C12—H12 | 118.6 | C41—C42—H42B | 109.5 |
C11—C12—H12 | 118.6 | H42A—C42—H42B | 109.5 |
C12—C13—C27 | 118.08 (18) | C41—C42—H42C | 109.5 |
C12—C13—C14 | 119.48 (17) | H42A—C42—H42C | 109.5 |
C27—C13—C14 | 122.30 (17) | H42B—C42—H42C | 109.5 |
C13—C14—C15 | 112.17 (15) | C41—C43—H43A | 109.5 |
C13—C14—H14A | 109.2 | C41—C43—H43B | 109.5 |
C15—C14—H14A | 109.2 | H43A—C43—H43B | 109.5 |
C13—C14—H14B | 109.2 | C41—C43—H43C | 109.5 |
C15—C14—H14B | 109.2 | H43A—C43—H43C | 109.5 |
H14A—C14—H14B | 107.9 | H43B—C43—H43C | 109.5 |
C16—C15—C26 | 118.59 (17) | C41—C44—H44A | 109.5 |
C16—C15—C14 | 120.49 (16) | C41—C44—H44B | 109.5 |
C26—C15—C14 | 120.90 (16) | H44A—C44—H44B | 109.5 |
C17—C16—C15 | 122.71 (17) | C41—C44—H44C | 109.5 |
C17—C16—H16 | 118.6 | H44A—C44—H44C | 109.5 |
C15—C16—H16 | 118.6 | H44B—C44—H44C | 109.5 |
C16—C17—C18 | 117.00 (16) | O3—C45—C46 | 112.23 (16) |
C16—C17—C33 | 122.90 (16) | O3—C45—H45A | 109.2 |
C18—C17—C33 | 120.10 (16) | C46—C45—H45A | 109.2 |
C19—C18—C17 | 122.30 (17) | O3—C45—H45B | 109.2 |
C19—C18—H18 | 118.9 | C46—C45—H45B | 109.2 |
C17—C18—H18 | 118.9 | H45A—C45—H45B | 107.9 |
C18—C19—C26 | 118.86 (16) | O7—C46—O8 | 125.6 (2) |
C18—C19—C20 | 120.93 (16) | O7—C46—C45 | 122.31 (19) |
C26—C19—C20 | 120.18 (16) | O8—C46—C45 | 112.11 (17) |
C19—C20—C21 | 113.16 (14) | O1—C47—C48 | 112.26 (15) |
C19—C20—H20A | 108.9 | O1—C47—H47A | 109.2 |
C21—C20—H20A | 108.9 | C48—C47—H47A | 109.2 |
C19—C20—H20B | 108.9 | O1—C47—H47B | 109.2 |
C21—C20—H20B | 108.9 | C48—C47—H47B | 109.2 |
H20A—C20—H20B | 107.8 | H47A—C47—H47B | 107.9 |
C25—C21—C22 | 118.12 (16) | O5—C48—O6 | 124.92 (18) |
C25—C21—C20 | 123.78 (16) | O5—C48—C47 | 124.79 (17) |
C22—C21—C20 | 118.08 (15) | O6—C48—C47 | 110.28 (16) |
C23—C22—C21 | 122.01 (16) | C49—N1—C51 | 122.67 (19) |
C23—C22—H22 | 119.0 | C49—N1—C50 | 120.78 (18) |
C21—C22—H22 | 119.0 | C51—N1—C50 | 116.54 (19) |
C22—C23—C24 | 117.15 (16) | C52—N2—C53 | 123.05 (17) |
C22—C23—C29 | 122.58 (16) | C52—N2—C54 | 120.43 (17) |
C24—C23—C29 | 120.20 (16) | C53—N2—C54 | 116.48 (17) |
C1—C24—C23 | 122.70 (17) | C55—N3—C57 | 121.07 (18) |
C1—C24—H24 | 118.6 | C55—N3—C56 | 121.23 (18) |
C23—C24—H24 | 118.6 | C57—N3—C56 | 117.69 (17) |
C21—C25—O1 | 120.67 (15) | O9—C49—N1 | 125.35 (19) |
C21—C25—C1 | 121.56 (16) | O9—C49—H49 | 117.3 |
O1—C25—C1 | 117.75 (15) | N1—C49—H49 | 117.3 |
O4—C26—C15 | 123.58 (16) | N1—C50—H50A | 109.5 |
O4—C26—C19 | 115.81 (15) | N1—C50—H50B | 109.5 |
C15—C26—C19 | 120.51 (16) | H50A—C50—H50B | 109.5 |
C9—C27—C13 | 121.30 (18) | N1—C50—H50C | 109.5 |
C9—C27—O3 | 119.87 (16) | H50A—C50—H50C | 109.5 |
C13—C27—O3 | 118.69 (17) | H50B—C50—H50C | 109.5 |
O2—C28—C3 | 123.10 (16) | N1—C51—H51A | 109.5 |
O2—C28—C7 | 116.64 (16) | N1—C51—H51B | 109.5 |
C3—C28—C7 | 120.25 (17) | H51A—C51—H51B | 109.5 |
C31—C29—C23 | 111.79 (15) | N1—C51—H51C | 109.5 |
C31—C29—C30 | 108.31 (16) | H51A—C51—H51C | 109.5 |
C23—C29—C30 | 110.24 (15) | H51B—C51—H51C | 109.5 |
C31—C29—C32 | 108.87 (17) | O10—C52—N2 | 126.59 (19) |
C23—C29—C32 | 108.05 (15) | O10—C52—H52 | 116.7 |
C30—C29—C32 | 109.56 (16) | N2—C52—H52 | 116.7 |
C29—C30—H30A | 109.5 | N2—C53—H53A | 109.5 |
C29—C30—H30B | 109.5 | N2—C53—H53B | 109.5 |
H30A—C30—H30B | 109.5 | H53A—C53—H53B | 109.5 |
C29—C30—H30C | 109.5 | N2—C53—H53C | 109.5 |
H30A—C30—H30C | 109.5 | H53A—C53—H53C | 109.5 |
H30B—C30—H30C | 109.5 | H53B—C53—H53C | 109.5 |
C29—C31—H31A | 109.5 | N2—C54—H54A | 109.5 |
C29—C31—H31B | 109.5 | N2—C54—H54B | 109.5 |
H31A—C31—H31B | 109.5 | H54A—C54—H54B | 109.5 |
C29—C31—H31C | 109.5 | N2—C54—H54C | 109.5 |
H31A—C31—H31C | 109.5 | H54A—C54—H54C | 109.5 |
H31B—C31—H31C | 109.5 | H54B—C54—H54C | 109.5 |
C29—C32—H32A | 109.5 | O11—C55—N3 | 124.9 (2) |
C29—C32—H32B | 109.5 | O11—C55—H55 | 117.6 |
H32A—C32—H32B | 109.5 | N3—C55—H55 | 117.6 |
C29—C32—H32C | 109.5 | N3—C56—H56A | 109.5 |
H32A—C32—H32C | 109.5 | N3—C56—H56B | 109.5 |
H32B—C32—H32C | 109.5 | H56A—C56—H56B | 109.5 |
C36—C33—C34 | 108.26 (17) | N3—C56—H56C | 109.5 |
C36—C33—C35 | 107.95 (17) | H56A—C56—H56C | 109.5 |
C34—C33—C35 | 108.72 (19) | H56B—C56—H56C | 109.5 |
C36—C33—C17 | 112.21 (15) | N3—C57—H57A | 109.5 |
C34—C33—C17 | 109.53 (16) | N3—C57—H57B | 109.5 |
C35—C33—C17 | 110.09 (16) | H57A—C57—H57B | 109.5 |
C33—C34—H34A | 109.5 | N3—C57—H57C | 109.5 |
C33—C34—H34B | 109.5 | H57A—C57—H57C | 109.5 |
H34A—C34—H34B | 109.5 | H57B—C57—H57C | 109.5 |
C24—C1—C2—C3 | 84.9 (2) | C16—C15—C26—C19 | −1.5 (3) |
C25—C1—C2—C3 | −93.1 (2) | C14—C15—C26—C19 | 176.88 (16) |
C1—C2—C3—C4 | −94.13 (19) | C18—C19—C26—O4 | 178.40 (15) |
C1—C2—C3—C28 | 83.2 (2) | C20—C19—C26—O4 | 0.3 (2) |
C28—C3—C4—C5 | 1.9 (3) | C18—C19—C26—C15 | 1.8 (3) |
C2—C3—C4—C5 | 179.30 (16) | C20—C19—C26—C15 | −176.36 (16) |
C3—C4—C5—C6 | −0.2 (3) | C10—C9—C27—C13 | 5.9 (3) |
C3—C4—C5—C41 | −179.72 (17) | C8—C9—C27—C13 | −170.33 (17) |
C4—C5—C6—C7 | −1.8 (3) | C10—C9—C27—O3 | −178.30 (16) |
C41—C5—C6—C7 | 177.75 (17) | C8—C9—C27—O3 | 5.4 (3) |
C5—C6—C7—C28 | 2.0 (3) | C12—C13—C27—C9 | −5.8 (3) |
C5—C6—C7—C8 | −175.09 (17) | C14—C13—C27—C9 | 169.77 (16) |
C6—C7—C8—C9 | 89.2 (2) | C12—C13—C27—O3 | 178.33 (15) |
C28—C7—C8—C9 | −87.8 (2) | C14—C13—C27—O3 | −6.1 (3) |
C7—C8—C9—C10 | −71.2 (2) | C45—O3—C27—C9 | 105.98 (19) |
C7—C8—C9—C27 | 104.9 (2) | C45—O3—C27—C13 | −78.1 (2) |
C27—C9—C10—C11 | −1.9 (3) | C4—C3—C28—O2 | 179.88 (16) |
C8—C9—C10—C11 | 174.44 (17) | C2—C3—C28—O2 | 2.5 (3) |
C9—C10—C11—C12 | −1.9 (3) | C4—C3—C28—C7 | −1.7 (3) |
C9—C10—C11—C37 | 178.02 (18) | C2—C3—C28—C7 | −179.02 (16) |
C10—C11—C12—C13 | 2.0 (3) | C6—C7—C28—O2 | 178.37 (16) |
C37—C11—C12—C13 | −177.92 (18) | C8—C7—C28—O2 | −4.5 (2) |
C11—C12—C13—C27 | 1.7 (3) | C6—C7—C28—C3 | −0.2 (3) |
C11—C12—C13—C14 | −174.00 (17) | C8—C7—C28—C3 | 176.91 (16) |
C12—C13—C14—C15 | 77.2 (2) | C22—C23—C29—C31 | 13.6 (2) |
C27—C13—C14—C15 | −98.3 (2) | C24—C23—C29—C31 | −169.48 (17) |
C13—C14—C15—C16 | −106.17 (19) | C22—C23—C29—C30 | 134.12 (17) |
C13—C14—C15—C26 | 75.5 (2) | C24—C23—C29—C30 | −48.9 (2) |
C26—C15—C16—C17 | 0.4 (3) | C22—C23—C29—C32 | −106.2 (2) |
C14—C15—C16—C17 | −177.92 (17) | C24—C23—C29—C32 | 70.8 (2) |
C15—C16—C17—C18 | 0.3 (3) | C16—C17—C33—C36 | −11.6 (3) |
C15—C16—C17—C33 | 179.93 (17) | C18—C17—C33—C36 | 168.02 (17) |
C16—C17—C18—C19 | 0.0 (3) | C16—C17—C33—C34 | 108.6 (2) |
C33—C17—C18—C19 | −179.63 (16) | C18—C17—C33—C34 | −71.7 (2) |
C17—C18—C19—C26 | −1.0 (3) | C16—C17—C33—C35 | −131.9 (2) |
C17—C18—C19—C20 | 177.07 (16) | C18—C17—C33—C35 | 47.8 (2) |
C18—C19—C20—C21 | 100.76 (19) | C10—C11—C37—C39 | 10.3 (3) |
C26—C19—C20—C21 | −81.2 (2) | C12—C11—C37—C39 | −169.77 (19) |
C19—C20—C21—C25 | 100.88 (19) | C10—C11—C37—C38 | 130.6 (2) |
C19—C20—C21—C22 | −77.8 (2) | C12—C11—C37—C38 | −49.4 (2) |
C25—C21—C22—C23 | −1.6 (3) | C10—C11—C37—C40 | −110.2 (2) |
C20—C21—C22—C23 | 177.19 (16) | C12—C11—C37—C40 | 69.7 (2) |
C21—C22—C23—C24 | −3.9 (2) | C4—C5—C41—C42 | −119.3 (2) |
C21—C22—C23—C29 | 173.17 (16) | C6—C5—C41—C42 | 61.2 (2) |
C25—C1—C24—C23 | 1.3 (3) | C4—C5—C41—C43 | 1.4 (3) |
C2—C1—C24—C23 | −176.87 (16) | C6—C5—C41—C43 | −178.06 (18) |
C22—C23—C24—C1 | 4.0 (3) | C4—C5—C41—C44 | 121.6 (2) |
C29—C23—C24—C1 | −173.07 (16) | C6—C5—C41—C44 | −57.9 (2) |
C22—C21—C25—O1 | −174.36 (14) | C27—O3—C45—C46 | −74.6 (2) |
C20—C21—C25—O1 | 6.9 (3) | O3—C45—C46—O7 | 119.8 (2) |
C22—C21—C25—C1 | 7.2 (3) | O3—C45—C46—O8 | −61.3 (2) |
C20—C21—C25—C1 | −171.49 (16) | C25—O1—C47—C48 | 110.92 (16) |
C47—O1—C25—C21 | 69.0 (2) | O1—C47—C48—O5 | 6.7 (3) |
C47—O1—C25—C1 | −112.54 (17) | O1—C47—C48—O6 | −173.95 (15) |
C24—C1—C25—C21 | −7.1 (3) | C51—N1—C49—O9 | 178.5 (2) |
C2—C1—C25—C21 | 171.04 (16) | C50—N1—C49—O9 | −2.7 (4) |
C24—C1—C25—O1 | 174.46 (15) | C53—N2—C52—O10 | 178.92 (19) |
C2—C1—C25—O1 | −7.4 (2) | C54—N2—C52—O10 | 1.4 (3) |
C16—C15—C26—O4 | −177.84 (16) | C57—N3—C55—O11 | 177.8 (2) |
C14—C15—C26—O4 | 0.5 (3) | C56—N3—C55—O11 | −1.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.84 | 1.95 | 2.762 (2) | 163 |
O4—H4···O3 | 0.84 | 1.96 | 2.780 (2) | 165 |
O6—H6···O9 | 0.84 | 1.75 | 2.584 (2) | 170 |
O8—H8···O11 | 0.84 | 1.75 | 2.581 (2) | 168 |
Experimental details
Crystal data | |
Chemical formula | C48H60O8·3C3H7NO |
Mr | 984.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 11.3624 (3), 35.224 (1), 13.7180 (4) |
β (°) | 96.991 (2) |
V (Å3) | 5449.6 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.66 |
Crystal size (mm) | 0.30 × 0.11 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Integration face-indexing of crystal Reference |
Tmin, Tmax | 0.862, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25773, 9142, 6845 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.593 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.127, 1.07 |
No. of reflections | 9142 |
No. of parameters | 662 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.28 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.84 | 1.95 | 2.762 (2) | 163 |
O4—H4···O3 | 0.84 | 1.96 | 2.780 (2) | 165 |
O6—H6···O9 | 0.84 | 1.75 | 2.584 (2) | 170 |
O8—H8···O11 | 0.84 | 1.75 | 2.581 (2) | 168 |
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Calixarenes have macrocyclic structural frameworks that are known to exist in a variety of conformations, and well developed synthetic procedures are available for functionaliztion at the upper or lower rim. Modification of the basic framework has led to applications in catalysis, ionic and molecular separations, sensors, scaffolds for supramolecular arrays, ligands for metal binding, and in host–guest interactions (Gutsche, 1998). Calixarenes functionalized with carboxylic acid groups have been shown to be active towards extraction of heavy metals (Dung & Ludwig, 1999), as well as to display complexation properties toward alkali and alkali earth metal cations (McKervey et al., 1996), and lanthanide cations (Arnaud-Neu et al., 1997).
This report describes the crystal structure of the title compound, (I), initially prepared by Ungaro & Pochini (1984) and subsequently by Collins et al. (1991), but of which the structure has not been reported previously. \sch
Compound (I) is a calix[4]arene in the cone conformation which has been functionalized at the lower rim with distal carboxylic acid groups. Intramolecular hydrogen bonding between the phenols and the O atoms of adjacent ether groups on the lower rim stabilize the cone conformation. Carboxylic acids tend to crystallize as like-like acid pairs that make up a common synthon in crystal engineering (Frankenbach & Etter, 1992). It is rare to obtain unlike acid pairs, although they can occur when the balance of shapes and intermolecular van der Waals forces is suitable, such as with the facial amphiphile Kemp's triacid (Childs & Hagen, 2002). A number of crystallizations from different solvent systems, including ones with potential carboxylic acid co-crystals, resulted in the formation of very fine needles. It was only from DMF/H2O (Ratio?) that we were able to grow sufficiently large needles for this study, which have a DMF clathrate molecule inside the cone of the calix[4]arene. It is common for calixarenes to host solvent molecules inside the cone, although only one other example of a DMF clathrate has been reported (Froidevaux et al., 2000). In both cases, the DMF molecule adopts a `methyl in, carbonyl out' orientation.
The calixarenes in (I) crystallize in a face-to-face pattern with the acid groups directed towards, but not interacting directly with inversion-related pairs. Instead, the other two DMF solvate molecules participate in intermolecular hydrogen bonding with the carboxylic acid groups on the lower rim of the calix[4]arene. However, each of the carboxylic acid groups of the diacid interacts differently with a DMF molecule. In one carboxylic acid group, the OH is hydrogen-bonded to the carbonyl atom O9 of a DMF molecule [D···A 2.582 (2) Å], and atom O5 of the carboxylic acid forms a hydrogen bond to the carbonyl C—H atom of the DMF molecule [D···A 2.690 (2) Å].
There are only a few cases of DMF-carboxylic acid inclusion compounds in which the formyl group of the DMF is involved in (C)H···O-type weak hydrogen-bonding interactions in addition to traditional (O)H···O-type hydrogen bonding, resulting in cyclic hydrogen-bonded pairs (Desiraju & Steiner, 1999). This cyclic group is decidedly non-planar in (I), with an angle of 128° between the planes of the carboxylic acid and amide.
The other carboxylic acid group has only one hydrogen bond between the carboxylic acid OH and the carbonyl atom O11 of the DMF molecule [D···A 2.578 (2) Å]. Instead of being positioned toward the O atom of the carboxylic acid, the carbonyl C—H is oriented towards atom O4 of a neighboring molecule in the lattice [D···A 3.19 Å]. The net balance of all intermolecular forces results in close interactions between acid atom O7 and O8, and C atoms of neighboring calixarenes (O7···C47A 3.07, O7···C48A 2.93 and O8···C45A 3.40 Å).