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Proton-pump inhibitors (PPI) are prodrugs used widely to treat acid-related diseases since the late 1980s. After an extensive research effort it has become clear that the fundamental interactions between metal atoms and PPIs are of paramount importance for both drug release and long-term therapeutic safety. Unfortunately, until now, very little information has been available on this topic. In this paper, we report the crystal structure analysis of a novel calcium–PPI compound incorporating bridging and terminal deprotonated (
R)-rabeprazole tricyclic ligands (
L), namely bis[μ-(
R)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3
H-benzofuro[5,6-
d]imidazol-1-ido]bis{dimethanol[(
R)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3
H-benzofuro[5,6-
d]imidazol-1-ido]calcium(II)} methanol hexasolvate, [Ca
2(C
20H
22N
3O
4S)
4(CH
3OH)
4]·6CH
3OH or [Ca
2(
L)
4(CH
3OH)
4]·6CH
3OH, which crystallizes from methanol in the polar
C2 space group. Using low-temperature microcrystal synchrotron radiation, we demonstrate that this compound is in the form of a beautiful `butterfly molecule', consisting of a
C2-symmetric dinuclear (CH
3OH)
2LCa
II(μ
2-
L)
2Ca
IIL(HOCH
3)
2 framework. A large amount of disorder is found within the bridging
L ligand and the conformation of the fused tetrahydrofuran ring exhibits great variety. All the sulfinyl groups remain intact and the nonbonded Ca
Ca distance is significantly longer than in other calcium dimers, indicating steric hindrance in the bridging ligands. Considerable hydrogen bonding and aromatic C—H
π interactions co-operate to stabilize the whole complex, as well as to facilitate supramolecular assembly. Additional investigations into the bond nature were made using density functional theory (DFT) methods at the B3LYP/6-31G(d) level; geometry optimization, Mulliken atomic charges, MEP (molecular electrostatic potential), HOMO–LUMO (highest occupied molecular orbital–lowest unoccupied molecular orbital), TDOS (total density of states), PDOS (partial density of states), COOP (crystal orbital overlap population) and vibrational spectra were calculated/recorded and assessed carefully.
Supporting information
CCDC reference: 885451
Data collection: ADSC Quantum Q315r software; cell refinement: XDS (Kabsch, 2010); data reduction: XDS (Kabsch, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Bis[µ-(
R)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3
H-benzofuro[5,6-
d]imidazol-1-ido]bis{dimethanol[(
R)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3
H-benzofuro[5,6-
d]imidazol-1-ido]calcium(II)} methanol hexasolvate
top
Crystal data top
[Ca2(C20H22N3SO4)4(CH4O)4]·6CH4O | F(000) = 2128 |
Mr = 2002.44 | Dx = 1.327 Mg m−3 |
Monoclinic, C2 | Synchrotron radiation, λ = 0.79987 Å |
a = 32.100 (6) Å | Cell parameters from 3062 reflections |
b = 10.560 (2) Å | θ = 2.9–32.8° |
c = 15.800 (3) Å | µ = 0.37 mm−1 |
β = 110.70 (3)° | T = 100 K |
V = 5010 (2) Å3 | Needle, yellow |
Z = 2 | 0.05 × 0.03 × 0.01 mm |
Data collection top
ADSC Q315r CCD area-detector diffractometer | Rint = 0.028 |
φ scans | θmax = 32.8°, θmin = 2.9° |
39409 measured reflections | h = −43→43 |
11723 independent reflections | k = −13→14 |
11544 reflections with I > 2σ(I) | l = −21→21 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0536P)2 + 2.6948P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.036 | (Δ/σ)max = 0.001 |
wR(F2) = 0.095 | Δρmax = 0.54 e Å−3 |
S = 1.08 | Δρmin = −0.36 e Å−3 |
11723 reflections | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
772 parameters | Extinction coefficient: 0.0096 (14) |
171 restraints | Absolute structure: Flack x determined using 5262 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Hydrogen site location: mixed | Absolute structure parameter: 0.049 (4) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ca1 | 0.06822 (2) | 0.70157 (4) | 1.04395 (3) | 0.02369 (12) | |
S1 | −0.00161 (2) | 0.65606 (6) | 0.82227 (4) | 0.02588 (14) | |
S2 | 0.13937 (2) | 0.78815 (6) | 0.93215 (4) | 0.02643 (14) | |
C22 | 0.22024 (8) | 0.8284 (2) | 1.17579 (17) | 0.0296 (5) | |
C24 | 0.25831 (9) | 0.8404 (3) | 1.33317 (19) | 0.0393 (6) | |
C29 | 0.18329 (8) | 0.7725 (2) | 1.19040 (16) | 0.0282 (5) | |
O6 | 0.22814 (11) | 0.7677 (4) | 1.44084 (17) | 0.0733 (8) | |
C28 | 0.18349 (9) | 0.7484 (3) | 1.27802 (17) | 0.0356 (5) | |
C27 | 0.22172 (10) | 0.7844 (3) | 1.34751 (18) | 0.0408 (6) | |
C23 | 0.25906 (9) | 0.8629 (3) | 1.2482 (2) | 0.0355 (6) | |
N4 | 0.21012 (7) | 0.8443 (2) | 1.08363 (15) | 0.0316 (4) | |
N5 | 0.15014 (7) | 0.7512 (2) | 1.10723 (14) | 0.0284 (4) | |
C21 | 0.16912 (7) | 0.7967 (2) | 1.05042 (16) | 0.0277 (4) | |
O5 | 0.09118 (5) | 0.77251 (17) | 0.92345 (11) | 0.0280 (3) | |
N6 | 0.09664 (8) | 0.5174 (2) | 0.81720 (17) | 0.0357 (5) | |
C35 | 0.14860 (8) | 0.6063 (2) | 0.75366 (17) | 0.0289 (5) | |
C31 | 0.13428 (8) | 0.5815 (2) | 0.82573 (17) | 0.0295 (5) | |
C30 | 0.15926 (9) | 0.6294 (3) | 0.91889 (18) | 0.0319 (5) | |
C34 | 0.12140 (8) | 0.5627 (2) | 0.66782 (17) | 0.0293 (5) | |
C32 | 0.07210 (10) | 0.4776 (3) | 0.7350 (2) | 0.0399 (6) | |
C33 | 0.08258 (9) | 0.4967 (3) | 0.65823 (19) | 0.0341 (5) | |
C36 | 0.19027 (9) | 0.6806 (3) | 0.76534 (18) | 0.0383 (6) | |
H36A | 0.1868 | 0.7672 | 0.7841 | 0.057* | |
H36B | 0.1955 | 0.6827 | 0.7079 | 0.057* | |
H36C | 0.2157 | 0.6402 | 0.8117 | 0.057* | |
O7 | 0.13589 (6) | 0.5910 (2) | 0.59946 (12) | 0.0351 (4) | |
C39 | 0.12775 (10) | 0.7728 (3) | 0.46104 (19) | 0.0393 (6) | |
C38 | 0.12635 (10) | 0.6310 (3) | 0.44593 (19) | 0.0384 (6) | |
C37 | 0.10781 (10) | 0.5600 (3) | 0.50824 (18) | 0.0370 (6) | |
O8 | 0.08504 (7) | 0.8137 (2) | 0.45738 (14) | 0.0396 (4) | |
C40 | 0.08297 (15) | 0.9461 (4) | 0.4633 (3) | 0.0652 (10) | |
H40A | 0.1057 | 0.9751 | 0.5196 | 0.098* | |
H40B | 0.0534 | 0.9709 | 0.4627 | 0.098* | |
H40C | 0.0883 | 0.9848 | 0.4116 | 0.098* | |
C15 | 0.03251 (11) | 0.9171 (3) | 0.72652 (17) | 0.0375 (6) | |
C18 | 0.13815 (12) | 1.1694 (3) | 0.6628 (2) | 0.0449 (7) | |
C11 | 0.00030 (11) | 0.8997 (3) | 0.76606 (18) | 0.0401 (6) | |
C19 | 0.17490 (12) | 1.0734 (4) | 0.6860 (3) | 0.0603 (11) | |
H19A | 0.1985 | 1.0965 | 0.7439 | 0.072* | |
H19B | 0.1632 | 0.9890 | 0.6934 | 0.072* | |
O9 | 0.07459 (6) | 0.50652 (18) | 0.97169 (13) | 0.0332 (4) | |
C41 | 0.05948 (10) | 0.3819 (3) | 0.9802 (2) | 0.0379 (6) | |
H41A | 0.0530 | 0.3759 | 1.0363 | 0.057* | |
H41B | 0.0826 | 0.3205 | 0.9819 | 0.057* | |
H41C | 0.0324 | 0.3637 | 0.9284 | 0.057* | |
C10 | −0.02921 (9) | 0.7841 (3) | 0.74592 (16) | 0.0333 (5) | |
C16 | 0.04041 (10) | 0.8240 (3) | 0.6626 (2) | 0.0384 (6) | |
H16A | 0.0547 | 0.7480 | 0.6960 | 0.058* | |
H16B | 0.0599 | 0.8620 | 0.6337 | 0.058* | |
H16C | 0.0119 | 0.8009 | 0.6162 | 0.058* | |
O11 | 0.15687 (10) | 0.2604 (3) | 0.9435 (2) | 0.0703 (8) | |
C43 | 0.17391 (18) | 0.1652 (5) | 1.0055 (5) | 0.0883 (16) | |
H43A | 0.2057 | 0.1550 | 1.0164 | 0.132* | |
H43B | 0.1583 | 0.0858 | 0.9819 | 0.132* | |
H43C | 0.1698 | 0.1869 | 1.0624 | 0.132* | |
O1 | −0.00056 (5) | 0.70304 (19) | 0.91445 (10) | 0.0282 (3) | |
N1 | −0.04585 (7) | 0.4451 (2) | 0.74046 (17) | 0.0344 (5) | |
C1 | −0.04603 (8) | 0.5458 (2) | 0.79054 (16) | 0.0264 (4) | |
N2 | −0.07982 (7) | 0.5626 (2) | 0.82100 (14) | 0.0291 (4) | |
C9 | −0.10572 (8) | 0.4569 (2) | 0.78553 (17) | 0.0304 (5) | |
C2 | −0.08507 (9) | 0.3854 (2) | 0.7362 (2) | 0.0369 (6) | |
C8 | −0.14608 (9) | 0.4188 (3) | 0.7945 (2) | 0.0389 (6) | |
H8 | −0.1605 | 0.4673 | 0.8267 | 0.047* | |
C3 | −0.10333 (12) | 0.2705 (3) | 0.6944 (3) | 0.0605 (10) | |
H3 | −0.0897 | 0.2221 | 0.6606 | 0.073* | |
O2 | −0.20248 (9) | 0.2528 (3) | 0.7528 (2) | 0.0676 (8) | |
O13 | 0.22822 (7) | 0.4258 (3) | −0.01411 (16) | 0.0505 (6) | |
C45 | 0.24726 (13) | 0.4639 (4) | 0.0777 (2) | 0.0591 (10) | |
H45A | 0.2798 | 0.4650 | 0.0960 | 0.089* | |
H45B | 0.2385 | 0.4042 | 0.1159 | 0.089* | |
H45C | 0.2366 | 0.5489 | 0.0847 | 0.089* | |
C17 | 0.1194 (4) | 1.1544 (10) | 0.7346 (9) | 0.041 (2) | 0.52 (2) |
H17A | 0.1436 | 1.1506 | 0.7946 | 0.049* | 0.52 (2) |
H17B | 0.0997 | 1.2266 | 0.7343 | 0.049* | 0.52 (2) |
O3 | 0.0944 (3) | 1.0372 (10) | 0.7161 (8) | 0.0305 (16) | 0.52 (2) |
C14 | 0.0644 (4) | 1.0180 (10) | 0.7578 (7) | 0.0286 (17) | 0.52 (2) |
C13 | 0.0610 (4) | 1.0960 (9) | 0.8256 (7) | 0.038 (2) | 0.52 (2) |
H13 | 0.0799 | 1.1674 | 0.8463 | 0.046* | 0.52 (2) |
C12 | 0.0290 (4) | 1.0657 (9) | 0.8619 (7) | 0.040 (2) | 0.52 (2) |
H12 | 0.0271 | 1.1173 | 0.9097 | 0.048* | 0.52 (2) |
N3 | 0.0004 (3) | 0.9694 (9) | 0.8349 (7) | 0.0328 (16) | 0.52 (2) |
O3' | 0.0810 (4) | 1.0556 (11) | 0.7031 (9) | 0.0333 (17) | 0.48 (2) |
C17' | 0.1026 (5) | 1.1789 (12) | 0.7143 (8) | 0.043 (2) | 0.48 (2) |
H17C | 0.1180 | 1.1982 | 0.7792 | 0.052* | 0.48 (2) |
H17D | 0.0805 | 1.2463 | 0.6871 | 0.052* | 0.48 (2) |
C14' | 0.0504 (4) | 1.0412 (11) | 0.7407 (8) | 0.034 (2) | 0.48 (2) |
C13' | 0.0405 (5) | 1.1295 (8) | 0.7968 (7) | 0.042 (2) | 0.48 (2) |
H13' | 0.0558 | 1.2081 | 0.8102 | 0.050* | 0.48 (2) |
C12' | 0.0084 (5) | 1.1008 (9) | 0.8322 (7) | 0.042 (2) | 0.48 (2) |
H12' | 0.0025 | 1.1608 | 0.8714 | 0.050* | 0.48 (2) |
N3' | −0.0154 (4) | 0.9926 (9) | 0.8147 (7) | 0.0370 (19) | 0.48 (2) |
C42 | 0.0897 (2) | 1.0227 (7) | 1.0804 (12) | 0.057 (3) | 0.73 (3) |
H42A | 0.0825 | 1.0957 | 1.1111 | 0.086* | 0.73 (3) |
H42B | 0.0825 | 1.0425 | 1.0162 | 0.086* | 0.73 (3) |
H42C | 0.1215 | 1.0033 | 1.1081 | 0.086* | 0.73 (3) |
C42' | 0.0909 (5) | 1.0093 (14) | 1.1213 (15) | 0.033 (4) | 0.27 (3) |
H42D | 0.0979 | 1.0162 | 1.1867 | 0.050* | 0.27 (3) |
H42E | 0.0767 | 1.0876 | 1.0918 | 0.050* | 0.27 (3) |
H42F | 0.1185 | 0.9953 | 1.1091 | 0.050* | 0.27 (3) |
O10 | 0.06343 (7) | 0.9126 (2) | 1.08924 (14) | 0.0382 (4) | |
H10O | 0.0445 | 0.9325 | 1.1143 | 0.046* | |
C20 | 0.2312 (3) | 0.9892 (9) | 0.6666 (12) | 0.059 (3) | 0.52 (3) |
H20A | 0.2503 | 1.0343 | 0.7205 | 0.089* | 0.52 (3) |
H20B | 0.2481 | 0.9703 | 0.6272 | 0.089* | 0.52 (3) |
H20C | 0.2208 | 0.9100 | 0.6847 | 0.089* | 0.52 (3) |
C20' | 0.2288 (3) | 0.9920 (7) | 0.6159 (14) | 0.053 (4) | 0.48 (3) |
H20D | 0.2561 | 1.0188 | 0.6643 | 0.079* | 0.48 (3) |
H20E | 0.2325 | 1.0011 | 0.5573 | 0.079* | 0.48 (3) |
H20F | 0.2226 | 0.9032 | 0.6252 | 0.079* | 0.48 (3) |
C25 | 0.29295 (11) | 0.8709 (4) | 1.4185 (3) | 0.0615 (9) | 0.575 (10) |
H25A | 0.2927 | 0.9620 | 1.4332 | 0.074* | 0.575 (10) |
H25B | 0.3228 | 0.8472 | 1.4184 | 0.074* | 0.575 (10) |
C26 | 0.2786 (2) | 0.7849 (8) | 1.4866 (4) | 0.0736 (16) | 0.575 (10) |
H26A | 0.2940 | 0.7021 | 1.4959 | 0.088* | 0.575 (10) |
H26B | 0.2858 | 0.8274 | 1.5459 | 0.088* | 0.575 (10) |
C25' | 0.29295 (11) | 0.8709 (4) | 1.4185 (3) | 0.0615 (9) | 0.425 (10) |
H25C | 0.3063 | 0.9551 | 1.4175 | 0.074* | 0.425 (10) |
H25D | 0.3166 | 0.8056 | 1.4372 | 0.074* | 0.425 (10) |
C26' | 0.2624 (3) | 0.8692 (11) | 1.4801 (6) | 0.0715 (18) | 0.425 (10) |
H26C | 0.2806 | 0.8495 | 1.5438 | 0.086* | 0.425 (10) |
H26D | 0.2479 | 0.9524 | 1.4781 | 0.086* | 0.425 (10) |
C7 | −0.16295 (10) | 0.3054 (3) | 0.7528 (3) | 0.0487 (7) | |
C4 | −0.14233 (12) | 0.2323 (3) | 0.7053 (3) | 0.0593 (9) | |
C6 | −0.20737 (16) | 0.1320 (4) | 0.7060 (5) | 0.0794 (12) | |
H6A | −0.2378 | 0.1246 | 0.6607 | 0.095* | 0.575 (10) |
H6B | −0.2028 | 0.0618 | 0.7499 | 0.095* | 0.575 (10) |
H6C | −0.2320 | 0.1364 | 0.6467 | 0.095* | 0.425 (10) |
H6D | −0.2142 | 0.0641 | 0.7423 | 0.095* | 0.425 (10) |
C5 | −0.1726 (3) | 0.1227 (8) | 0.6580 (8) | 0.0683 (17) | 0.575 (10) |
H5A | −0.1567 | 0.0407 | 0.6699 | 0.082* | 0.575 (10) |
H5B | −0.1864 | 0.1365 | 0.5920 | 0.082* | 0.575 (10) |
C5' | −0.1649 (4) | 0.1052 (10) | 0.6931 (11) | 0.067 (2) | 0.425 (10) |
H5'1 | −0.1701 | 0.0710 | 0.6318 | 0.081* | 0.425 (10) |
H5'2 | −0.1468 | 0.0438 | 0.7386 | 0.081* | 0.425 (10) |
C44 | 0.0398 (5) | 0.2588 (12) | 0.4399 (7) | 0.075 (4) | 0.48 (2) |
H44A | 0.0722 | 0.2670 | 0.4676 | 0.112* | 0.48 (2) |
H44B | 0.0324 | 0.2002 | 0.3886 | 0.112* | 0.48 (2) |
H44C | 0.0279 | 0.2262 | 0.4847 | 0.112* | 0.48 (2) |
C44' | 0.0101 (4) | 0.2440 (10) | 0.3988 (11) | 0.087 (5) | 0.52 (2) |
H44D | 0.0353 | 0.1954 | 0.3943 | 0.130* | 0.52 (2) |
H44E | −0.0159 | 0.2326 | 0.3434 | 0.130* | 0.52 (2) |
H44F | 0.0031 | 0.2140 | 0.4509 | 0.130* | 0.52 (2) |
O12 | 0.02164 (11) | 0.3745 (4) | 0.4103 (2) | 0.0729 (8) | |
H12O | 0.029 (2) | 0.407 (6) | 0.360 (3) | 0.087* | |
O4 | 0.19259 (8) | 1.0688 (2) | 0.6174 (2) | 0.0621 (7) | |
H33 | 0.0637 (14) | 0.462 (5) | 0.605 (2) | 0.075* | |
H10A | −0.0351 (17) | 0.755 (5) | 0.686 (2) | 0.075* | |
H10B | −0.0571 (11) | 0.803 (5) | 0.754 (3) | 0.075* | |
H30A | 0.1535 (18) | 0.575 (6) | 0.964 (4) | 0.075* | |
H30B | 0.1883 (18) | 0.634 (5) | 0.927 (4) | 0.075* | |
H28 | 0.1564 (17) | 0.708 (6) | 1.287 (3) | 0.075* | |
H37A | 0.0756 (10) | 0.585 (5) | 0.497 (3) | 0.075* | |
H37B | 0.1045 (17) | 0.468 (6) | 0.500 (4) | 0.075* | |
H39A | 0.1349 (17) | 0.815 (6) | 0.412 (4) | 0.075* | |
H39B | 0.1499 (17) | 0.809 (5) | 0.524 (3) | 0.075* | |
H38A | 0.1081 (18) | 0.612 (5) | 0.386 (4) | 0.075* | |
H38B | 0.1571 (18) | 0.593 (6) | 0.459 (4) | 0.075* | |
H23 | 0.2841 (18) | 0.901 (5) | 1.239 (3) | 0.075* | |
H32 | 0.0444 (18) | 0.430 (5) | 0.731 (4) | 0.075* | |
H18A | 0.1193 (15) | 1.160 (6) | 0.599 (2) | 0.075* | |
H18B | 0.1505 (9) | 1.260 (2) | 0.6666 (19) | 0.075* | |
H9O | 0.0820 | 0.5110 | 0.9233 | 0.075* | |
H13O | 0.2505 | 0.3935 | −0.0317 | 0.075* | |
H11O | 0.1779 | 0.3194 | 0.9382 | 0.075* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ca1 | 0.01931 (19) | 0.0268 (2) | 0.0233 (2) | 0.00009 (16) | 0.00540 (15) | −0.00255 (16) |
S1 | 0.0235 (2) | 0.0305 (3) | 0.0230 (2) | −0.0076 (2) | 0.00733 (19) | −0.0031 (2) |
S2 | 0.0220 (2) | 0.0288 (3) | 0.0264 (3) | −0.00028 (19) | 0.00589 (19) | 0.0027 (2) |
C22 | 0.0242 (10) | 0.0261 (10) | 0.0321 (11) | 0.0036 (8) | 0.0020 (9) | −0.0010 (9) |
C24 | 0.0290 (11) | 0.0355 (12) | 0.0395 (13) | 0.0081 (10) | −0.0049 (10) | −0.0137 (10) |
C29 | 0.0237 (10) | 0.0266 (11) | 0.0304 (11) | 0.0043 (8) | 0.0049 (8) | −0.0030 (9) |
O6 | 0.0779 (16) | 0.103 (2) | 0.0373 (11) | 0.0177 (16) | 0.0185 (11) | −0.0065 (13) |
C28 | 0.0318 (12) | 0.0430 (14) | 0.0282 (11) | 0.0078 (11) | 0.0058 (9) | −0.0032 (10) |
C27 | 0.0376 (12) | 0.0494 (15) | 0.0301 (11) | 0.0125 (12) | 0.0053 (10) | −0.0089 (11) |
C23 | 0.0250 (11) | 0.0272 (11) | 0.0427 (14) | 0.0037 (9) | −0.0025 (10) | −0.0046 (10) |
N4 | 0.0239 (9) | 0.0311 (10) | 0.0346 (10) | −0.0013 (8) | 0.0038 (8) | 0.0028 (8) |
N5 | 0.0235 (9) | 0.0320 (10) | 0.0267 (9) | 0.0028 (8) | 0.0051 (7) | 0.0011 (8) |
C21 | 0.0238 (10) | 0.0273 (11) | 0.0276 (10) | 0.0007 (8) | 0.0037 (8) | 0.0013 (8) |
O5 | 0.0229 (7) | 0.0299 (8) | 0.0277 (7) | 0.0006 (6) | 0.0046 (6) | −0.0017 (6) |
N6 | 0.0393 (12) | 0.0349 (11) | 0.0398 (12) | −0.0025 (9) | 0.0224 (10) | −0.0042 (9) |
C35 | 0.0273 (10) | 0.0258 (10) | 0.0337 (12) | 0.0052 (9) | 0.0110 (9) | 0.0034 (9) |
C31 | 0.0310 (11) | 0.0267 (11) | 0.0324 (11) | 0.0066 (9) | 0.0131 (9) | 0.0020 (9) |
C30 | 0.0305 (11) | 0.0331 (13) | 0.0330 (12) | 0.0082 (9) | 0.0122 (10) | 0.0043 (9) |
C34 | 0.0305 (11) | 0.0258 (11) | 0.0342 (12) | 0.0050 (9) | 0.0148 (10) | 0.0011 (9) |
C32 | 0.0396 (14) | 0.0366 (14) | 0.0495 (16) | −0.0079 (11) | 0.0231 (12) | −0.0099 (12) |
C33 | 0.0339 (12) | 0.0306 (12) | 0.0397 (13) | −0.0001 (10) | 0.0155 (10) | −0.0074 (10) |
C36 | 0.0341 (12) | 0.0487 (17) | 0.0323 (11) | −0.0063 (11) | 0.0120 (10) | −0.0004 (11) |
O7 | 0.0332 (9) | 0.0443 (11) | 0.0277 (8) | −0.0024 (8) | 0.0105 (7) | 0.0003 (7) |
C39 | 0.0407 (14) | 0.0462 (16) | 0.0291 (12) | −0.0025 (12) | 0.0100 (10) | 0.0004 (11) |
C38 | 0.0401 (14) | 0.0454 (16) | 0.0293 (12) | 0.0027 (12) | 0.0117 (11) | −0.0020 (11) |
C37 | 0.0399 (13) | 0.0370 (14) | 0.0314 (12) | −0.0026 (11) | 0.0093 (11) | −0.0044 (10) |
O8 | 0.0417 (10) | 0.0387 (11) | 0.0355 (9) | 0.0009 (8) | 0.0100 (8) | −0.0052 (8) |
C40 | 0.065 (2) | 0.0461 (19) | 0.074 (3) | 0.0002 (17) | 0.0115 (19) | −0.0177 (18) |
C15 | 0.0544 (16) | 0.0290 (12) | 0.0285 (12) | −0.0158 (11) | 0.0138 (11) | −0.0032 (9) |
C18 | 0.0569 (17) | 0.0321 (14) | 0.0485 (15) | −0.0184 (13) | 0.0223 (14) | −0.0042 (12) |
C11 | 0.0614 (17) | 0.0306 (13) | 0.0302 (12) | −0.0188 (12) | 0.0187 (12) | −0.0033 (10) |
C19 | 0.0478 (17) | 0.0427 (17) | 0.068 (2) | −0.0159 (14) | −0.0070 (16) | 0.0184 (16) |
O9 | 0.0407 (10) | 0.0277 (8) | 0.0368 (9) | −0.0049 (7) | 0.0206 (8) | −0.0051 (7) |
C41 | 0.0440 (14) | 0.0292 (12) | 0.0432 (14) | −0.0059 (11) | 0.0188 (12) | −0.0051 (11) |
C10 | 0.0406 (13) | 0.0306 (12) | 0.0235 (10) | −0.0100 (10) | 0.0052 (9) | 0.0014 (9) |
C16 | 0.0440 (14) | 0.0281 (12) | 0.0449 (14) | −0.0094 (11) | 0.0179 (12) | −0.0039 (11) |
O11 | 0.0514 (14) | 0.0664 (19) | 0.082 (2) | −0.0008 (13) | 0.0094 (14) | −0.0150 (15) |
C43 | 0.071 (3) | 0.057 (2) | 0.125 (5) | −0.001 (2) | 0.019 (3) | 0.002 (3) |
O1 | 0.0226 (7) | 0.0383 (9) | 0.0225 (7) | −0.0035 (7) | 0.0064 (6) | −0.0020 (7) |
N1 | 0.0301 (10) | 0.0244 (10) | 0.0479 (13) | −0.0038 (8) | 0.0128 (9) | −0.0040 (9) |
C1 | 0.0240 (10) | 0.0254 (10) | 0.0264 (10) | −0.0036 (8) | 0.0048 (8) | 0.0023 (8) |
N2 | 0.0245 (9) | 0.0320 (10) | 0.0288 (9) | −0.0082 (8) | 0.0070 (7) | −0.0006 (8) |
C9 | 0.0274 (11) | 0.0268 (11) | 0.0319 (11) | −0.0048 (9) | 0.0042 (9) | 0.0048 (9) |
C2 | 0.0318 (12) | 0.0213 (11) | 0.0527 (15) | −0.0025 (9) | 0.0090 (11) | 0.0011 (10) |
C8 | 0.0294 (12) | 0.0397 (14) | 0.0454 (14) | −0.0088 (11) | 0.0107 (11) | 0.0031 (12) |
C3 | 0.0461 (17) | 0.0269 (14) | 0.109 (3) | −0.0081 (12) | 0.0287 (19) | −0.0197 (16) |
O2 | 0.0447 (12) | 0.0476 (13) | 0.109 (2) | −0.0223 (11) | 0.0254 (13) | −0.0009 (14) |
O13 | 0.0382 (10) | 0.0593 (14) | 0.0489 (12) | 0.0150 (10) | 0.0092 (9) | −0.0146 (11) |
C45 | 0.0547 (19) | 0.069 (2) | 0.0448 (17) | 0.0287 (18) | 0.0067 (15) | −0.0058 (16) |
C17 | 0.042 (5) | 0.032 (4) | 0.056 (5) | −0.016 (4) | 0.027 (4) | −0.013 (3) |
O3 | 0.028 (4) | 0.026 (3) | 0.041 (4) | −0.009 (3) | 0.017 (3) | −0.004 (2) |
C14 | 0.033 (4) | 0.023 (4) | 0.029 (4) | −0.005 (3) | 0.010 (3) | 0.001 (3) |
C13 | 0.044 (4) | 0.031 (3) | 0.046 (4) | −0.016 (3) | 0.024 (4) | −0.014 (3) |
C12 | 0.049 (5) | 0.035 (3) | 0.041 (4) | −0.011 (3) | 0.024 (4) | −0.013 (3) |
N3 | 0.035 (4) | 0.031 (3) | 0.036 (4) | −0.012 (3) | 0.016 (3) | −0.005 (3) |
O3' | 0.032 (4) | 0.027 (3) | 0.042 (4) | −0.007 (3) | 0.013 (4) | −0.005 (2) |
C17' | 0.048 (6) | 0.040 (5) | 0.046 (5) | −0.023 (4) | 0.021 (4) | −0.007 (3) |
C14' | 0.039 (6) | 0.027 (4) | 0.034 (4) | −0.006 (4) | 0.009 (4) | 0.007 (3) |
C13' | 0.053 (6) | 0.028 (3) | 0.047 (4) | −0.014 (4) | 0.023 (4) | −0.005 (3) |
C12' | 0.055 (6) | 0.032 (3) | 0.045 (4) | −0.012 (4) | 0.027 (4) | −0.010 (3) |
N3' | 0.044 (5) | 0.030 (3) | 0.035 (4) | −0.010 (3) | 0.012 (4) | −0.001 (3) |
C42 | 0.053 (3) | 0.033 (3) | 0.087 (7) | −0.010 (2) | 0.028 (4) | −0.019 (4) |
C42' | 0.029 (5) | 0.033 (6) | 0.036 (8) | 0.000 (4) | 0.008 (5) | −0.001 (5) |
O10 | 0.0381 (9) | 0.0338 (10) | 0.0434 (10) | 0.0013 (8) | 0.0152 (8) | −0.0095 (8) |
C20 | 0.049 (4) | 0.060 (5) | 0.067 (8) | −0.003 (3) | 0.019 (4) | 0.017 (4) |
C20' | 0.050 (4) | 0.034 (3) | 0.086 (10) | 0.005 (3) | 0.039 (5) | 0.011 (4) |
C25 | 0.0367 (13) | 0.0509 (16) | 0.0636 (17) | 0.0134 (12) | −0.0236 (12) | −0.0291 (13) |
C26 | 0.071 (3) | 0.086 (3) | 0.040 (2) | 0.039 (3) | −0.009 (2) | −0.022 (2) |
C25' | 0.0367 (13) | 0.0509 (16) | 0.0636 (17) | 0.0134 (12) | −0.0236 (12) | −0.0291 (13) |
C26' | 0.069 (3) | 0.074 (3) | 0.048 (3) | 0.019 (3) | −0.010 (2) | −0.017 (3) |
C7 | 0.0332 (12) | 0.0318 (13) | 0.076 (2) | −0.0101 (11) | 0.0124 (13) | 0.0104 (13) |
C4 | 0.0421 (15) | 0.0216 (12) | 0.107 (3) | −0.0102 (11) | 0.0180 (16) | −0.0034 (14) |
C6 | 0.059 (2) | 0.0428 (18) | 0.131 (3) | −0.0227 (16) | 0.026 (2) | −0.003 (2) |
C5 | 0.053 (3) | 0.025 (3) | 0.121 (4) | −0.010 (2) | 0.023 (3) | −0.005 (3) |
C5' | 0.049 (3) | 0.026 (3) | 0.113 (5) | −0.014 (3) | 0.011 (3) | 0.001 (3) |
C44 | 0.072 (9) | 0.085 (7) | 0.061 (5) | −0.001 (5) | 0.015 (5) | 0.007 (5) |
C44' | 0.067 (7) | 0.066 (6) | 0.132 (11) | 0.007 (5) | 0.041 (7) | 0.049 (6) |
O12 | 0.0686 (18) | 0.083 (2) | 0.0690 (18) | −0.0034 (16) | 0.0266 (15) | 0.0075 (16) |
O4 | 0.0377 (11) | 0.0375 (12) | 0.106 (2) | −0.0024 (10) | 0.0192 (13) | −0.0023 (13) |
Geometric parameters (Å, º) top
Ca1—O10 | 2.362 (2) | C43—H43C | 0.9800 |
Ca1—O5 | 2.3920 (18) | O1—Ca1i | 2.4814 (17) |
Ca1—O9 | 2.3986 (19) | N1—C1 | 1.327 (3) |
Ca1—O1 | 2.4225 (19) | N1—C2 | 1.388 (3) |
Ca1—O1i | 2.4814 (17) | C1—N2 | 1.345 (3) |
Ca1—N2i | 2.507 (2) | N2—C9 | 1.386 (3) |
Ca1—N5 | 2.516 (2) | N2—Ca1i | 2.507 (2) |
S1—O1 | 1.5277 (17) | C9—C2 | 1.409 (4) |
S1—C1 | 1.771 (2) | C9—C8 | 1.411 (4) |
S1—C10 | 1.820 (3) | C2—C3 | 1.406 (4) |
S2—O5 | 1.5129 (17) | C8—C7 | 1.382 (4) |
S2—C21 | 1.775 (2) | C8—H8 | 0.9500 |
S2—C30 | 1.832 (3) | C3—C4 | 1.383 (5) |
C22—N4 | 1.385 (3) | C3—H3 | 0.9500 |
C22—C23 | 1.409 (3) | O2—C7 | 1.385 (4) |
C22—C29 | 1.415 (4) | O2—C6 | 1.455 (6) |
C24—C23 | 1.372 (5) | O13—C45 | 1.419 (4) |
C24—C27 | 1.403 (5) | O13—H13O | 0.9194 |
C24—C25' | 1.448 (4) | C45—H45A | 0.9800 |
C24—C25 | 1.448 (4) | C45—H45B | 0.9800 |
C29—N5 | 1.386 (3) | C45—H45C | 0.9800 |
C29—C28 | 1.405 (4) | C17—O3 | 1.448 (15) |
O6—C27 | 1.426 (4) | C17—H17A | 0.9900 |
O6—C26' | 1.504 (11) | C17—H17B | 0.9900 |
O6—C26 | 1.533 (8) | O3—C14 | 1.362 (14) |
C28—C27 | 1.380 (4) | C14—C13 | 1.387 (12) |
C28—H28 | 1.02 (5) | C13—C12 | 1.379 (9) |
C23—H23 | 0.95 (5) | C13—H13 | 0.9500 |
N4—C21 | 1.331 (3) | C12—N3 | 1.334 (10) |
N5—C21 | 1.339 (3) | C12—H12 | 0.9500 |
N6—C32 | 1.327 (4) | O3'—C14' | 1.326 (17) |
N6—C31 | 1.350 (3) | O3'—C17' | 1.457 (16) |
C35—C31 | 1.395 (3) | C17'—H17C | 0.9900 |
C35—C34 | 1.406 (4) | C17'—H17D | 0.9900 |
C35—C36 | 1.505 (4) | C14'—C13' | 1.397 (15) |
C31—C30 | 1.494 (4) | C13'—C12' | 1.370 (10) |
C30—H30A | 0.98 (6) | C13'—H13' | 0.9500 |
C30—H30B | 0.90 (5) | C12'—N3' | 1.347 (11) |
C34—O7 | 1.352 (3) | C12'—H12' | 0.9500 |
C34—C33 | 1.388 (4) | C42—O10 | 1.471 (9) |
C32—C33 | 1.383 (4) | C42—H42A | 0.9800 |
C32—H32 | 1.00 (5) | C42—H42B | 0.9800 |
C33—H33 | 0.92 (3) | C42—H42C | 0.9800 |
C36—H36A | 0.9800 | C42'—O10 | 1.327 (14) |
C36—H36B | 0.9800 | C42'—H42D | 0.9800 |
C36—H36C | 0.9800 | C42'—H42E | 0.9800 |
O7—C37 | 1.442 (3) | C42'—H42F | 0.9800 |
C39—O8 | 1.419 (4) | O10—H10O | 0.8611 |
C39—C38 | 1.514 (4) | C20—O4 | 1.471 (9) |
C39—H39A | 0.98 (5) | C20—H20A | 0.9800 |
C39—H39B | 1.07 (5) | C20—H20B | 0.9800 |
C38—C37 | 1.516 (4) | C20—H20C | 0.9800 |
C38—H38A | 0.94 (6) | C20'—O4 | 1.423 (8) |
C38—H38B | 1.02 (6) | C20'—H20D | 0.9800 |
C37—H37A | 1.02 (3) | C20'—H20E | 0.9800 |
C37—H37B | 0.98 (6) | C20'—H20F | 0.9800 |
O8—C40 | 1.404 (5) | C25—C26 | 1.595 (11) |
C40—H40A | 0.9800 | C25—H25A | 0.9900 |
C40—H40B | 0.9800 | C25—H25B | 0.9900 |
C40—H40C | 0.9800 | C26—H26A | 0.9900 |
C15—C11 | 1.397 (4) | C26—H26B | 0.9900 |
C15—C14' | 1.416 (12) | C25'—C26' | 1.608 (12) |
C15—C14 | 1.438 (10) | C25'—H25C | 0.9900 |
C15—C16 | 1.494 (4) | C25'—H25D | 0.9900 |
C18—C17 | 1.468 (11) | C26'—H26C | 0.9900 |
C18—C19 | 1.500 (6) | C26'—H26D | 0.9900 |
C18—C17' | 1.620 (13) | C7—C4 | 1.396 (6) |
C18—H18A | 0.98 (3) | C4—C5' | 1.505 (11) |
C18—H18B | 1.03 (2) | C4—C5 | 1.526 (9) |
C11—N3 | 1.313 (9) | C6—C5' | 1.475 (14) |
C11—N3' | 1.443 (12) | C6—C5 | 1.558 (11) |
C11—C10 | 1.508 (4) | C6—H6A | 0.9900 |
C19—O4 | 1.391 (6) | C6—H6B | 0.9900 |
C19—H19A | 0.9900 | C6—H6C | 0.9900 |
C19—H19B | 0.9900 | C6—H6D | 0.9900 |
O9—C41 | 1.425 (3) | C5—H5A | 0.9900 |
O9—H9O | 0.8781 | C5—H5B | 0.9900 |
C41—H41A | 0.9800 | C5'—H5'1 | 0.9900 |
C41—H41B | 0.9800 | C5'—H5'2 | 0.9900 |
C41—H41C | 0.9800 | C44—O12 | 1.363 (13) |
C10—H10A | 0.95 (3) | C44—H44A | 0.9800 |
C10—H10B | 0.97 (3) | C44—H44B | 0.9800 |
C16—H16A | 0.9800 | C44—H44C | 0.9800 |
C16—H16B | 0.9800 | C44'—O12 | 1.422 (12) |
C16—H16C | 0.9800 | C44'—H44D | 0.9800 |
O11—C43 | 1.375 (7) | C44'—H44E | 0.9800 |
O11—H11O | 0.9436 | C44'—H44F | 0.9800 |
C43—H43A | 0.9800 | O12—H12O | 0.97 (3) |
C43—H43B | 0.9800 | | |
| | | |
O10—Ca1—O5 | 90.98 (7) | S1—O1—Ca1i | 121.60 (9) |
O10—Ca1—O9 | 168.52 (7) | Ca1—O1—Ca1i | 113.45 (6) |
O5—Ca1—O9 | 77.75 (6) | C1—N1—C2 | 101.4 (2) |
O10—Ca1—O1 | 96.45 (7) | N1—C1—N2 | 119.6 (2) |
O5—Ca1—O1 | 76.76 (6) | N1—C1—S1 | 121.54 (19) |
O9—Ca1—O1 | 78.99 (7) | N2—C1—S1 | 118.86 (18) |
O10—Ca1—O1i | 75.94 (7) | C1—N2—C9 | 101.2 (2) |
O5—Ca1—O1i | 138.91 (6) | C1—N2—Ca1i | 119.07 (15) |
O9—Ca1—O1i | 111.19 (7) | C9—N2—Ca1i | 134.66 (17) |
O1—Ca1—O1i | 66.55 (6) | N2—C9—C2 | 108.9 (2) |
O10—Ca1—N2i | 107.48 (8) | N2—C9—C8 | 129.0 (3) |
O5—Ca1—N2i | 150.00 (6) | C2—C9—C8 | 122.1 (2) |
O9—Ca1—N2i | 83.71 (7) | N1—C2—C3 | 129.4 (3) |
O1—Ca1—N2i | 122.66 (7) | N1—C2—C9 | 109.0 (2) |
O1i—Ca1—N2i | 70.05 (6) | C3—C2—C9 | 121.6 (3) |
O10—Ca1—N5 | 81.59 (7) | C7—C8—C9 | 114.7 (3) |
O5—Ca1—N5 | 71.23 (7) | C7—C8—H8 | 122.6 |
O9—Ca1—N5 | 96.61 (7) | C9—C8—H8 | 122.6 |
O1—Ca1—N5 | 147.87 (7) | C4—C3—C2 | 116.0 (3) |
O1i—Ca1—N5 | 141.54 (6) | C4—C3—H3 | 122.0 |
N2i—Ca1—N5 | 87.92 (7) | C2—C3—H3 | 122.0 |
O1—S1—C1 | 103.16 (11) | C7—O2—C6 | 106.6 (3) |
O1—S1—C10 | 103.43 (12) | C45—O13—H13O | 108.3 |
C1—S1—C10 | 98.41 (12) | O13—C45—H45A | 109.5 |
O5—S2—C21 | 104.69 (11) | O13—C45—H45B | 109.5 |
O5—S2—C30 | 106.03 (12) | H45A—C45—H45B | 109.5 |
C21—S2—C30 | 95.02 (12) | O13—C45—H45C | 109.5 |
N4—C22—C23 | 129.3 (3) | H45A—C45—H45C | 109.5 |
N4—C22—C29 | 108.8 (2) | H45B—C45—H45C | 109.5 |
C23—C22—C29 | 121.8 (3) | O3—C17—C18 | 106.5 (8) |
C23—C24—C27 | 122.4 (2) | O3—C17—H17A | 110.4 |
C23—C24—C25' | 126.8 (3) | C18—C17—H17A | 110.4 |
C27—C24—C25' | 110.7 (3) | O3—C17—H17B | 110.4 |
C23—C24—C25 | 126.8 (3) | C18—C17—H17B | 110.4 |
C27—C24—C25 | 110.7 (3) | H17A—C17—H17B | 108.6 |
N5—C29—C28 | 129.7 (2) | C14—O3—C17 | 117.8 (10) |
N5—C29—C22 | 108.7 (2) | O3—C14—C13 | 123.2 (9) |
C28—C29—C22 | 121.6 (2) | O3—C14—C15 | 119.0 (9) |
C27—O6—C26' | 99.0 (5) | C13—C14—C15 | 117.7 (7) |
C27—O6—C26 | 102.4 (4) | C12—C13—C14 | 117.2 (6) |
C27—C28—C29 | 115.3 (3) | C12—C13—H13 | 121.4 |
C27—C28—H28 | 124 (3) | C14—C13—H13 | 121.4 |
C29—C28—H28 | 120 (3) | N3—C12—C13 | 125.0 (6) |
C28—C27—C24 | 123.2 (3) | N3—C12—H12 | 117.5 |
C28—C27—O6 | 123.5 (3) | C13—C12—H12 | 117.5 |
C24—C27—O6 | 113.3 (3) | C11—N3—C12 | 119.5 (6) |
C24—C23—C22 | 115.7 (3) | C14'—O3'—C17' | 116.4 (11) |
C24—C23—H23 | 122 (3) | O3'—C17'—C18 | 105.9 (8) |
C22—C23—H23 | 123 (3) | O3'—C17'—H17C | 110.6 |
C21—N4—C22 | 101.6 (2) | C18—C17'—H17C | 110.6 |
C21—N5—C29 | 101.5 (2) | O3'—C17'—H17D | 110.6 |
C21—N5—Ca1 | 117.86 (15) | C18—C17'—H17D | 110.6 |
C29—N5—Ca1 | 139.01 (16) | H17C—C17'—H17D | 108.7 |
N4—C21—N5 | 119.5 (2) | O3'—C14'—C13' | 125.4 (10) |
N4—C21—S2 | 121.55 (19) | O3'—C14'—C15 | 111.0 (10) |
N5—C21—S2 | 118.98 (17) | C13'—C14'—C15 | 123.2 (9) |
S2—O5—Ca1 | 123.69 (10) | C12'—C13'—C14' | 119.0 (7) |
C32—N6—C31 | 117.2 (2) | C12'—C13'—H13' | 120.5 |
C31—C35—C34 | 117.0 (2) | C14'—C13'—H13' | 120.5 |
C31—C35—C36 | 122.2 (2) | N3'—C12'—C13' | 123.8 (7) |
C34—C35—C36 | 120.7 (2) | N3'—C12'—H12' | 118.1 |
N6—C31—C35 | 123.6 (2) | C13'—C12'—H12' | 118.1 |
N6—C31—C30 | 114.7 (2) | C12'—N3'—C11 | 114.0 (8) |
C35—C31—C30 | 121.6 (2) | O10—C42—H42A | 109.5 |
C31—C30—S2 | 109.58 (17) | O10—C42—H42B | 109.5 |
C31—C30—H30A | 110 (3) | H42A—C42—H42B | 109.5 |
S2—C30—H30A | 107 (3) | O10—C42—H42C | 109.5 |
C31—C30—H30B | 109 (3) | H42A—C42—H42C | 109.5 |
S2—C30—H30B | 109 (4) | H42B—C42—H42C | 109.5 |
H30A—C30—H30B | 113 (5) | O10—C42'—H42D | 109.5 |
O7—C34—C33 | 124.9 (2) | O10—C42'—H42E | 109.5 |
O7—C34—C35 | 115.2 (2) | H42D—C42'—H42E | 109.5 |
C33—C34—C35 | 119.8 (2) | O10—C42'—H42F | 109.5 |
N6—C32—C33 | 124.6 (3) | H42D—C42'—H42F | 109.5 |
N6—C32—H32 | 115 (3) | H42E—C42'—H42F | 109.5 |
C33—C32—H32 | 120 (3) | C42'—O10—Ca1 | 137.4 (7) |
C32—C33—C34 | 117.7 (3) | C42—O10—Ca1 | 128.0 (4) |
C32—C33—H33 | 117 (3) | C42'—O10—H10O | 96.8 |
C34—C33—H33 | 125 (3) | C42—O10—H10O | 111.8 |
C35—C36—H36A | 109.5 | Ca1—O10—H10O | 120.2 |
C35—C36—H36B | 109.5 | O4—C20—H20A | 109.5 |
H36A—C36—H36B | 109.5 | O4—C20—H20B | 109.5 |
C35—C36—H36C | 109.5 | H20A—C20—H20B | 109.5 |
H36A—C36—H36C | 109.5 | O4—C20—H20C | 109.5 |
H36B—C36—H36C | 109.5 | H20A—C20—H20C | 109.5 |
C34—O7—C37 | 118.6 (2) | H20B—C20—H20C | 109.5 |
O8—C39—C38 | 108.7 (3) | O4—C20'—H20D | 109.5 |
O8—C39—H39A | 109 (3) | O4—C20'—H20E | 109.5 |
C38—C39—H39A | 109 (3) | H20D—C20'—H20E | 109.5 |
O8—C39—H39B | 104 (3) | O4—C20'—H20F | 109.5 |
C38—C39—H39B | 118 (3) | H20D—C20'—H20F | 109.5 |
H39A—C39—H39B | 108 (4) | H20E—C20'—H20F | 109.5 |
C39—C38—C37 | 112.5 (2) | C24—C25—C26 | 101.1 (4) |
C39—C38—H38A | 110 (3) | C24—C25—H25A | 111.6 |
C37—C38—H38A | 107 (3) | C26—C25—H25A | 111.6 |
C39—C38—H38B | 113 (3) | C24—C25—H25B | 111.6 |
C37—C38—H38B | 105 (3) | C26—C25—H25B | 111.6 |
H38A—C38—H38B | 109 (4) | H25A—C25—H25B | 109.4 |
O7—C37—C38 | 106.7 (2) | O6—C26—C25 | 105.0 (4) |
O7—C37—H37A | 110 (3) | O6—C26—H26A | 110.8 |
C38—C37—H37A | 112 (3) | C25—C26—H26A | 110.8 |
O7—C37—H37B | 111 (3) | O6—C26—H26B | 110.8 |
C38—C37—H37B | 116 (3) | C25—C26—H26B | 110.8 |
H37A—C37—H37B | 100 (4) | H26A—C26—H26B | 108.8 |
C40—O8—C39 | 111.6 (3) | C24—C25'—C26' | 97.4 (4) |
O8—C40—H40A | 109.5 | C24—C25'—H25C | 112.3 |
O8—C40—H40B | 109.5 | C26'—C25'—H25C | 112.3 |
H40A—C40—H40B | 109.5 | C24—C25'—H25D | 112.3 |
O8—C40—H40C | 109.5 | C26'—C25'—H25D | 112.3 |
H40A—C40—H40C | 109.5 | H25C—C25'—H25D | 109.9 |
H40B—C40—H40C | 109.5 | O6—C26'—C25' | 105.7 (6) |
C11—C15—C14' | 111.9 (6) | O6—C26'—H26C | 110.6 |
C11—C15—C14 | 119.6 (5) | C25'—C26'—H26C | 110.6 |
C11—C15—C16 | 123.0 (2) | O6—C26'—H26D | 110.6 |
C14'—C15—C16 | 124.1 (6) | C25'—C26'—H26D | 110.6 |
C14—C15—C16 | 116.7 (5) | H26C—C26'—H26D | 108.7 |
C17—C18—C19 | 103.8 (6) | C8—C7—O2 | 123.5 (3) |
C19—C18—C17' | 123.5 (6) | C8—C7—C4 | 123.7 (3) |
C17—C18—H18A | 121 (3) | O2—C7—C4 | 112.7 (3) |
C19—C18—H18A | 109 (3) | C3—C4—C7 | 121.9 (3) |
C17'—C18—H18A | 104 (3) | C3—C4—C5' | 131.3 (6) |
C17—C18—H18B | 108.1 (16) | C7—C4—C5' | 105.3 (6) |
C19—C18—H18B | 111.0 (15) | C3—C4—C5 | 127.4 (5) |
C17'—C18—H18B | 103.9 (16) | C7—C4—C5 | 110.0 (4) |
H18A—C18—H18B | 104 (4) | O2—C6—C5' | 107.4 (5) |
N3—C11—C15 | 120.8 (4) | O2—C6—C5 | 109.6 (4) |
C15—C11—N3' | 127.0 (4) | O2—C6—H6A | 109.8 |
N3—C11—C10 | 116.5 (4) | C5—C6—H6A | 109.8 |
C15—C11—C10 | 121.4 (3) | O2—C6—H6B | 109.8 |
N3'—C11—C10 | 110.6 (5) | C5—C6—H6B | 109.8 |
O4—C19—C18 | 109.6 (3) | H6A—C6—H6B | 108.2 |
O4—C19—H19A | 109.8 | O2—C6—H6C | 110.2 |
C18—C19—H19A | 109.8 | C5'—C6—H6C | 110.2 |
O4—C19—H19B | 109.8 | O2—C6—H6D | 110.2 |
C18—C19—H19B | 109.8 | C5'—C6—H6D | 110.2 |
H19A—C19—H19B | 108.2 | H6C—C6—H6D | 108.5 |
C41—O9—Ca1 | 131.18 (16) | C4—C5—C6 | 99.0 (6) |
C41—O9—H9O | 109.8 | C4—C5—H5A | 112.0 |
Ca1—O9—H9O | 117.6 | C6—C5—H5A | 112.0 |
O9—C41—H41A | 109.5 | C4—C5—H5B | 112.0 |
O9—C41—H41B | 109.5 | C6—C5—H5B | 112.0 |
H41A—C41—H41B | 109.5 | H5A—C5—H5B | 109.7 |
O9—C41—H41C | 109.5 | C6—C5'—C4 | 103.7 (8) |
H41A—C41—H41C | 109.5 | C6—C5'—H5'1 | 111.0 |
H41B—C41—H41C | 109.5 | C4—C5'—H5'1 | 111.0 |
C11—C10—S1 | 109.81 (19) | C6—C5'—H5'2 | 111.0 |
C11—C10—H10A | 111 (3) | C4—C5'—H5'2 | 111.0 |
S1—C10—H10A | 107 (3) | H5'1—C5'—H5'2 | 109.0 |
C11—C10—H10B | 110 (3) | O12—C44—H44A | 109.5 |
S1—C10—H10B | 109 (3) | O12—C44—H44B | 109.5 |
H10A—C10—H10B | 109 (4) | H44A—C44—H44B | 109.5 |
C15—C16—H16A | 109.5 | O12—C44—H44C | 109.5 |
C15—C16—H16B | 109.5 | H44A—C44—H44C | 109.5 |
H16A—C16—H16B | 109.5 | H44B—C44—H44C | 109.5 |
C15—C16—H16C | 109.5 | O12—C44'—H44D | 109.5 |
H16A—C16—H16C | 109.5 | O12—C44'—H44E | 109.5 |
H16B—C16—H16C | 109.5 | H44D—C44'—H44E | 109.5 |
C43—O11—H11O | 115.4 | O12—C44'—H44F | 109.5 |
O11—C43—H43A | 109.5 | H44D—C44'—H44F | 109.5 |
O11—C43—H43B | 109.5 | H44E—C44'—H44F | 109.5 |
H43A—C43—H43B | 109.5 | C44—O12—H12O | 114 (4) |
O11—C43—H43C | 109.5 | C44'—O12—H12O | 112 (4) |
H43A—C43—H43C | 109.5 | C19—O4—C20' | 126.3 (8) |
H43B—C43—H43C | 109.5 | C19—O4—C20 | 96.2 (8) |
S1—O1—Ca1 | 120.64 (9) | | |
| | | |
N4—C22—C29—N5 | 1.0 (3) | C2—N1—C1—N2 | 0.2 (3) |
C23—C22—C29—N5 | 179.1 (2) | C2—N1—C1—S1 | 177.61 (19) |
N4—C22—C29—C28 | −178.2 (2) | O1—S1—C1—N1 | −148.4 (2) |
C23—C22—C29—C28 | −0.1 (4) | C10—S1—C1—N1 | 105.6 (2) |
N5—C29—C28—C27 | −178.2 (3) | O1—S1—C1—N2 | 29.1 (2) |
C22—C29—C28—C27 | 0.8 (4) | C10—S1—C1—N2 | −76.9 (2) |
C29—C28—C27—C24 | −0.4 (4) | N1—C1—N2—C9 | 0.0 (3) |
C29—C28—C27—O6 | 180.0 (3) | S1—C1—N2—C9 | −177.53 (17) |
C23—C24—C27—C28 | −0.6 (5) | N1—C1—N2—Ca1i | 158.33 (18) |
C25'—C24—C27—C28 | 178.4 (3) | S1—C1—N2—Ca1i | −19.2 (2) |
C25—C24—C27—C28 | 178.4 (3) | C1—N2—C9—C2 | −0.1 (3) |
C23—C24—C27—O6 | 179.0 (3) | Ca1i—N2—C9—C2 | −153.2 (2) |
C25'—C24—C27—O6 | −1.9 (4) | C1—N2—C9—C8 | 179.1 (3) |
C25—C24—C27—O6 | −1.9 (4) | Ca1i—N2—C9—C8 | 26.1 (4) |
C26'—O6—C27—C28 | −156.2 (5) | C1—N1—C2—C3 | −178.1 (4) |
C26—O6—C27—C28 | 164.1 (4) | C1—N1—C2—C9 | −0.2 (3) |
C26'—O6—C27—C24 | 24.2 (5) | N2—C9—C2—N1 | 0.2 (3) |
C26—O6—C27—C24 | −15.5 (5) | C8—C9—C2—N1 | −179.1 (2) |
C27—C24—C23—C22 | 1.3 (4) | N2—C9—C2—C3 | 178.3 (3) |
C25'—C24—C23—C22 | −177.6 (3) | C8—C9—C2—C3 | −1.1 (5) |
C25—C24—C23—C22 | −177.6 (3) | N2—C9—C8—C7 | −178.0 (3) |
N4—C22—C23—C24 | 176.8 (3) | C2—C9—C8—C7 | 1.2 (4) |
C29—C22—C23—C24 | −0.9 (4) | N1—C2—C3—C4 | 177.1 (3) |
C23—C22—N4—C21 | −178.6 (3) | C9—C2—C3—C4 | −0.5 (6) |
C29—C22—N4—C21 | −0.6 (3) | C19—C18—C17—O3 | −73.5 (7) |
C28—C29—N5—C21 | 178.2 (3) | C18—C17—O3—C14 | −162.9 (8) |
C22—C29—N5—C21 | −0.8 (3) | C17—O3—C14—C13 | −9.1 (12) |
C28—C29—N5—Ca1 | 14.5 (4) | C17—O3—C14—C15 | 166.7 (8) |
C22—C29—N5—Ca1 | −164.62 (19) | C11—C15—C14—O3 | −177.3 (6) |
C22—N4—C21—N5 | 0.1 (3) | C16—C15—C14—O3 | 12.0 (9) |
C22—N4—C21—S2 | −178.21 (18) | C11—C15—C14—C13 | −1.3 (9) |
C29—N5—C21—N4 | 0.5 (3) | C16—C15—C14—C13 | −172.0 (6) |
Ca1—N5—C21—N4 | 168.51 (18) | O3—C14—C13—C12 | 179.9 (8) |
C29—N5—C21—S2 | 178.83 (18) | C15—C14—C13—C12 | 4.1 (12) |
Ca1—N5—C21—S2 | −13.1 (3) | C14—C13—C12—N3 | −2.0 (14) |
O5—S2—C21—N4 | −161.4 (2) | C15—C11—N3—C12 | 6.3 (10) |
C30—S2—C21—N4 | 90.6 (2) | C10—C11—N3—C12 | 173.4 (6) |
O5—S2—C21—N5 | 20.3 (2) | C13—C12—N3—C11 | −3.4 (13) |
C30—S2—C21—N5 | −87.7 (2) | C14'—O3'—C17'—C18 | 179.7 (8) |
C21—S2—O5—Ca1 | −19.16 (15) | C19—C18—C17'—O3' | −58.0 (9) |
C30—S2—O5—Ca1 | 80.59 (13) | C17'—O3'—C14'—C13' | −6.5 (15) |
C32—N6—C31—C35 | −0.7 (4) | C17'—O3'—C14'—C15 | −178.9 (8) |
C32—N6—C31—C30 | 177.1 (2) | C11—C15—C14'—O3' | 179.7 (7) |
C34—C35—C31—N6 | 1.0 (4) | C16—C15—C14'—O3' | −11.3 (11) |
C36—C35—C31—N6 | 178.6 (3) | C11—C15—C14'—C13' | 7.1 (11) |
C34—C35—C31—C30 | −176.7 (2) | C16—C15—C14'—C13' | 176.1 (7) |
C36—C35—C31—C30 | 1.0 (4) | O3'—C14'—C13'—C12' | −179.0 (10) |
N6—C31—C30—S2 | −89.6 (2) | C15—C14'—C13'—C12' | −7.5 (14) |
C35—C31—C30—S2 | 88.2 (3) | C14'—C13'—C12'—N3' | −1.5 (15) |
O5—S2—C30—C31 | 64.2 (2) | C13'—C12'—N3'—C11 | 8.9 (13) |
C21—S2—C30—C31 | 171.04 (19) | C15—C11—N3'—C12' | −9.1 (9) |
C31—C35—C34—O7 | 178.5 (2) | C10—C11—N3'—C12' | −177.6 (6) |
C36—C35—C34—O7 | 0.9 (3) | C23—C24—C25—C26 | −163.4 (4) |
C31—C35—C34—C33 | −0.9 (4) | C27—C24—C25—C26 | 17.6 (4) |
C36—C35—C34—C33 | −178.6 (2) | C27—O6—C26—C25 | 25.3 (5) |
C31—N6—C32—C33 | 0.3 (4) | C24—C25—C26—O6 | −26.3 (5) |
N6—C32—C33—C34 | −0.3 (5) | C23—C24—C25'—C26' | 159.3 (5) |
O7—C34—C33—C32 | −178.8 (3) | C27—C24—C25'—C26' | −19.7 (5) |
C35—C34—C33—C32 | 0.6 (4) | C27—O6—C26'—C25' | −35.5 (6) |
C33—C34—O7—C37 | 5.1 (4) | C24—C25'—C26'—O6 | 34.5 (6) |
C35—C34—O7—C37 | −174.3 (2) | C9—C8—C7—O2 | −179.1 (3) |
O8—C39—C38—C37 | −51.8 (3) | C9—C8—C7—C4 | 0.2 (5) |
C34—O7—C37—C38 | 165.9 (2) | C6—O2—C7—C8 | −177.4 (4) |
C39—C38—C37—O7 | −58.3 (3) | C6—O2—C7—C4 | 3.3 (5) |
C38—C39—O8—C40 | −175.0 (3) | C2—C3—C4—C7 | 1.8 (6) |
C14—C15—C11—N3 | −4.0 (6) | C2—C3—C4—C5' | −162.0 (9) |
C16—C15—C11—N3 | 166.1 (6) | C2—C3—C4—C5 | 171.2 (6) |
C14'—C15—C11—N3' | 1.3 (7) | C8—C7—C4—C3 | −1.8 (6) |
C16—C15—C11—N3' | −167.8 (6) | O2—C7—C4—C3 | 177.6 (4) |
C14'—C15—C11—C10 | 168.8 (6) | C8—C7—C4—C5' | 165.7 (7) |
C14—C15—C11—C10 | −170.5 (6) | O2—C7—C4—C5' | −15.0 (7) |
C16—C15—C11—C10 | −0.4 (5) | C8—C7—C4—C5 | −172.8 (5) |
C17—C18—C19—O4 | 173.9 (5) | O2—C7—C4—C5 | 6.5 (7) |
C17'—C18—C19—O4 | 165.7 (5) | C7—O2—C6—C5' | 10.2 (8) |
N3—C11—C10—S1 | −80.3 (6) | C7—O2—C6—C5 | −11.6 (7) |
C15—C11—C10—S1 | 86.7 (3) | C3—C4—C5—C6 | 177.2 (5) |
N3'—C11—C10—S1 | −104.0 (5) | C7—C4—C5—C6 | −12.3 (7) |
O1—S1—C10—C11 | 68.0 (2) | O2—C6—C5—C4 | 14.3 (8) |
C1—S1—C10—C11 | 173.7 (2) | O2—C6—C5'—C4 | −18.5 (11) |
C1—S1—O1—Ca1 | 128.47 (12) | C3—C4—C5'—C6 | −174.2 (6) |
C10—S1—O1—Ca1 | −129.39 (13) | C7—C4—C5'—C6 | 20.1 (10) |
C1—S1—O1—Ca1i | −26.68 (14) | C18—C19—O4—C20' | 178.1 (6) |
C10—S1—O1—Ca1i | 75.46 (14) | C18—C19—O4—C20 | 169.9 (5) |
Symmetry code: (i) −x, y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17A···O11ii | 0.99 | 2.52 | 3.285 (12) | 134 |
C13—H13···O11ii | 0.95 | 2.60 | 3.451 (9) | 150 |
C17′—H17C···O11ii | 0.99 | 2.54 | 3.527 (12) | 177 |
O10—H10O···N3i | 0.86 | 1.92 | 2.780 (8) | 176 |
O10—H10O···N3′i | 0.86 | 1.81 | 2.654 (10) | 167 |
C26—H26A···O4iii | 0.99 | 2.43 | 3.137 (8) | 128 |
C25′—H25C···O7iv | 0.99 | 2.43 | 3.341 (5) | 152 |
C25′—H25D···O4iii | 0.99 | 2.63 | 3.301 (4) | 125 |
O12—H12O···N1v | 0.97 (3) | 1.89 (3) | 2.853 (4) | 171 (6) |
C10—H10A···O8v | 0.95 (3) | 2.35 (4) | 3.092 (3) | 135 (4) |
C30—H30B···O13vi | 0.90 (5) | 2.55 (6) | 2.998 (3) | 112 (4) |
C32—H32···O12v | 1.00 (5) | 2.54 (5) | 3.260 (5) | 128 (4) |
O9—H9O···N6 | 0.88 | 1.90 | 2.774 (3) | 178 |
O13—H13O···N4vii | 0.92 | 1.81 | 2.721 (3) | 170 |
O11—H11O···O13vi | 0.94 | 1.89 | 2.767 (4) | 153 |
C16—H16B···O3 | 0.98 | 2.31 | 2.785 (11) | 109 |
C19—H19B···O3 | 0.99 | 2.41 | 2.813 (11) | 104 |
C36—H36B···O7 | 0.98 | 2.28 | 2.753 (3) | 108 |
Symmetry codes: (i) −x, y, −z+2; (ii) x, y+1, z; (iii) −x+1/2, y−1/2, −z+2; (iv) −x+1/2, y+1/2, −z+2; (v) −x, y, −z+1; (vi) x, y, z+1; (vii) −x+1/2, y−1/2, −z+1. |
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