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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-3H-benzofuro[5,6-d]imidazol-1-ido]bis­{di­methanol[(R)-2-({[4-(3-meth­oxy­prop­oxy)-3-methyl­pyridin-2-yl]meth­yl}sulfin­yl)-6,7-di­hydro-3H-benzofuro[5,6-d]imidazol-1-ido]calcium(II)} methanol hexa­solvate, [Ca2(C20H22N3O4S)4(CH3OH)4]·6CH3OH or [Ca2(L)4(CH3OH)4]·6CH3OH, 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 (CH3OH)2LCaII2-L)2CaIIL(HOCH3)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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616004216/lf3028sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004216/lf3028Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616004216/lf3028sup3.pdf
Supplementary figures and tables

CCDC reference: 885451

Computing details top

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-3H-benzofuro[5,6-d]imidazol-1-ido]bis{dimethanol[(R)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3H-benzofuro[5,6-d]imidazol-1-ido]calcium(II)} methanol hexasolvate top
Crystal data top
[Ca2(C20H22N3SO4)4(CH4O)4]·6CH4OF(000) = 2128
Mr = 2002.44Dx = 1.327 Mg m3
Monoclinic, C2Synchrotron radiation, λ = 0.79987 Å
a = 32.100 (6) ÅCell parameters from 3062 reflections
b = 10.560 (2) Åθ = 2.9–32.8°
c = 15.800 (3) ŵ = 0.37 mm1
β = 110.70 (3)°T = 100 K
V = 5010 (2) Å3Needle, yellow
Z = 20.05 × 0.03 × 0.01 mm
Data collection top
ADSC Q315r CCD area-detector
diffractometer
Rint = 0.028
φ scansθmax = 32.8°, θmin = 2.9°
39409 measured reflectionsh = 4343
11723 independent reflectionsk = 1314
11544 reflections with I > 2σ(I)l = 2121
Refinement top
Refinement on F2H 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) = 0.095Δρmax = 0.54 e Å3
S = 1.08Δρmin = 0.36 e Å3
11723 reflectionsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
772 parametersExtinction coefficient: 0.0096 (14)
171 restraintsAbsolute structure: Flack x determined using 5262 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixedAbsolute 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
xyzUiso*/UeqOcc. (<1)
Ca10.06822 (2)0.70157 (4)1.04395 (3)0.02369 (12)
S10.00161 (2)0.65606 (6)0.82227 (4)0.02588 (14)
S20.13937 (2)0.78815 (6)0.93215 (4)0.02643 (14)
C220.22024 (8)0.8284 (2)1.17579 (17)0.0296 (5)
C240.25831 (9)0.8404 (3)1.33317 (19)0.0393 (6)
C290.18329 (8)0.7725 (2)1.19040 (16)0.0282 (5)
O60.22814 (11)0.7677 (4)1.44084 (17)0.0733 (8)
C280.18349 (9)0.7484 (3)1.27802 (17)0.0356 (5)
C270.22172 (10)0.7844 (3)1.34751 (18)0.0408 (6)
C230.25906 (9)0.8629 (3)1.2482 (2)0.0355 (6)
N40.21012 (7)0.8443 (2)1.08363 (15)0.0316 (4)
N50.15014 (7)0.7512 (2)1.10723 (14)0.0284 (4)
C210.16912 (7)0.7967 (2)1.05042 (16)0.0277 (4)
O50.09118 (5)0.77251 (17)0.92345 (11)0.0280 (3)
N60.09664 (8)0.5174 (2)0.81720 (17)0.0357 (5)
C350.14860 (8)0.6063 (2)0.75366 (17)0.0289 (5)
C310.13428 (8)0.5815 (2)0.82573 (17)0.0295 (5)
C300.15926 (9)0.6294 (3)0.91889 (18)0.0319 (5)
C340.12140 (8)0.5627 (2)0.66782 (17)0.0293 (5)
C320.07210 (10)0.4776 (3)0.7350 (2)0.0399 (6)
C330.08258 (9)0.4967 (3)0.65823 (19)0.0341 (5)
C360.19027 (9)0.6806 (3)0.76534 (18)0.0383 (6)
H36A0.18680.76720.78410.057*
H36B0.19550.68270.70790.057*
H36C0.21570.64020.81170.057*
O70.13589 (6)0.5910 (2)0.59946 (12)0.0351 (4)
C390.12775 (10)0.7728 (3)0.46104 (19)0.0393 (6)
C380.12635 (10)0.6310 (3)0.44593 (19)0.0384 (6)
C370.10781 (10)0.5600 (3)0.50824 (18)0.0370 (6)
O80.08504 (7)0.8137 (2)0.45738 (14)0.0396 (4)
C400.08297 (15)0.9461 (4)0.4633 (3)0.0652 (10)
H40A0.10570.97510.51960.098*
H40B0.05340.97090.46270.098*
H40C0.08830.98480.41160.098*
C150.03251 (11)0.9171 (3)0.72652 (17)0.0375 (6)
C180.13815 (12)1.1694 (3)0.6628 (2)0.0449 (7)
C110.00030 (11)0.8997 (3)0.76606 (18)0.0401 (6)
C190.17490 (12)1.0734 (4)0.6860 (3)0.0603 (11)
H19A0.19851.09650.74390.072*
H19B0.16320.98900.69340.072*
O90.07459 (6)0.50652 (18)0.97169 (13)0.0332 (4)
C410.05948 (10)0.3819 (3)0.9802 (2)0.0379 (6)
H41A0.05300.37591.03630.057*
H41B0.08260.32050.98190.057*
H41C0.03240.36370.92840.057*
C100.02921 (9)0.7841 (3)0.74592 (16)0.0333 (5)
C160.04041 (10)0.8240 (3)0.6626 (2)0.0384 (6)
H16A0.05470.74800.69600.058*
H16B0.05990.86200.63370.058*
H16C0.01190.80090.61620.058*
O110.15687 (10)0.2604 (3)0.9435 (2)0.0703 (8)
C430.17391 (18)0.1652 (5)1.0055 (5)0.0883 (16)
H43A0.20570.15501.01640.132*
H43B0.15830.08580.98190.132*
H43C0.16980.18691.06240.132*
O10.00056 (5)0.70304 (19)0.91445 (10)0.0282 (3)
N10.04585 (7)0.4451 (2)0.74046 (17)0.0344 (5)
C10.04603 (8)0.5458 (2)0.79054 (16)0.0264 (4)
N20.07982 (7)0.5626 (2)0.82100 (14)0.0291 (4)
C90.10572 (8)0.4569 (2)0.78553 (17)0.0304 (5)
C20.08507 (9)0.3854 (2)0.7362 (2)0.0369 (6)
C80.14608 (9)0.4188 (3)0.7945 (2)0.0389 (6)
H80.16050.46730.82670.047*
C30.10333 (12)0.2705 (3)0.6944 (3)0.0605 (10)
H30.08970.22210.66060.073*
O20.20248 (9)0.2528 (3)0.7528 (2)0.0676 (8)
O130.22822 (7)0.4258 (3)0.01411 (16)0.0505 (6)
C450.24726 (13)0.4639 (4)0.0777 (2)0.0591 (10)
H45A0.27980.46500.09600.089*
H45B0.23850.40420.11590.089*
H45C0.23660.54890.08470.089*
C170.1194 (4)1.1544 (10)0.7346 (9)0.041 (2)0.52 (2)
H17A0.14361.15060.79460.049*0.52 (2)
H17B0.09971.22660.73430.049*0.52 (2)
O30.0944 (3)1.0372 (10)0.7161 (8)0.0305 (16)0.52 (2)
C140.0644 (4)1.0180 (10)0.7578 (7)0.0286 (17)0.52 (2)
C130.0610 (4)1.0960 (9)0.8256 (7)0.038 (2)0.52 (2)
H130.07991.16740.84630.046*0.52 (2)
C120.0290 (4)1.0657 (9)0.8619 (7)0.040 (2)0.52 (2)
H120.02711.11730.90970.048*0.52 (2)
N30.0004 (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)
H17C0.11801.19820.77920.052*0.48 (2)
H17D0.08051.24630.68710.052*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)
H13'0.05581.20810.81020.050*0.48 (2)
C12'0.0084 (5)1.1008 (9)0.8322 (7)0.042 (2)0.48 (2)
H12'0.00251.16080.87140.050*0.48 (2)
N3'0.0154 (4)0.9926 (9)0.8147 (7)0.0370 (19)0.48 (2)
C420.0897 (2)1.0227 (7)1.0804 (12)0.057 (3)0.73 (3)
H42A0.08251.09571.11110.086*0.73 (3)
H42B0.08251.04251.01620.086*0.73 (3)
H42C0.12151.00331.10810.086*0.73 (3)
C42'0.0909 (5)1.0093 (14)1.1213 (15)0.033 (4)0.27 (3)
H42D0.09791.01621.18670.050*0.27 (3)
H42E0.07671.08761.09180.050*0.27 (3)
H42F0.11850.99531.10910.050*0.27 (3)
O100.06343 (7)0.9126 (2)1.08924 (14)0.0382 (4)
H10O0.04450.93251.11430.046*
C200.2312 (3)0.9892 (9)0.6666 (12)0.059 (3)0.52 (3)
H20A0.25031.03430.72050.089*0.52 (3)
H20B0.24810.97030.62720.089*0.52 (3)
H20C0.22080.91000.68470.089*0.52 (3)
C20'0.2288 (3)0.9920 (7)0.6159 (14)0.053 (4)0.48 (3)
H20D0.25611.01880.66430.079*0.48 (3)
H20E0.23251.00110.55730.079*0.48 (3)
H20F0.22260.90320.62520.079*0.48 (3)
C250.29295 (11)0.8709 (4)1.4185 (3)0.0615 (9)0.575 (10)
H25A0.29270.96201.43320.074*0.575 (10)
H25B0.32280.84721.41840.074*0.575 (10)
C260.2786 (2)0.7849 (8)1.4866 (4)0.0736 (16)0.575 (10)
H26A0.29400.70211.49590.088*0.575 (10)
H26B0.28580.82741.54590.088*0.575 (10)
C25'0.29295 (11)0.8709 (4)1.4185 (3)0.0615 (9)0.425 (10)
H25C0.30630.95511.41750.074*0.425 (10)
H25D0.31660.80561.43720.074*0.425 (10)
C26'0.2624 (3)0.8692 (11)1.4801 (6)0.0715 (18)0.425 (10)
H26C0.28060.84951.54380.086*0.425 (10)
H26D0.24790.95241.47810.086*0.425 (10)
C70.16295 (10)0.3054 (3)0.7528 (3)0.0487 (7)
C40.14233 (12)0.2323 (3)0.7053 (3)0.0593 (9)
C60.20737 (16)0.1320 (4)0.7060 (5)0.0794 (12)
H6A0.23780.12460.66070.095*0.575 (10)
H6B0.20280.06180.74990.095*0.575 (10)
H6C0.23200.13640.64670.095*0.425 (10)
H6D0.21420.06410.74230.095*0.425 (10)
C50.1726 (3)0.1227 (8)0.6580 (8)0.0683 (17)0.575 (10)
H5A0.15670.04070.66990.082*0.575 (10)
H5B0.18640.13650.59200.082*0.575 (10)
C5'0.1649 (4)0.1052 (10)0.6931 (11)0.067 (2)0.425 (10)
H5'10.17010.07100.63180.081*0.425 (10)
H5'20.14680.04380.73860.081*0.425 (10)
C440.0398 (5)0.2588 (12)0.4399 (7)0.075 (4)0.48 (2)
H44A0.07220.26700.46760.112*0.48 (2)
H44B0.03240.20020.38860.112*0.48 (2)
H44C0.02790.22620.48470.112*0.48 (2)
C44'0.0101 (4)0.2440 (10)0.3988 (11)0.087 (5)0.52 (2)
H44D0.03530.19540.39430.130*0.52 (2)
H44E0.01590.23260.34340.130*0.52 (2)
H44F0.00310.21400.45090.130*0.52 (2)
O120.02164 (11)0.3745 (4)0.4103 (2)0.0729 (8)
H12O0.029 (2)0.407 (6)0.360 (3)0.087*
O40.19259 (8)1.0688 (2)0.6174 (2)0.0621 (7)
H330.0637 (14)0.462 (5)0.605 (2)0.075*
H10A0.0351 (17)0.755 (5)0.686 (2)0.075*
H10B0.0571 (11)0.803 (5)0.754 (3)0.075*
H30A0.1535 (18)0.575 (6)0.964 (4)0.075*
H30B0.1883 (18)0.634 (5)0.927 (4)0.075*
H280.1564 (17)0.708 (6)1.287 (3)0.075*
H37A0.0756 (10)0.585 (5)0.497 (3)0.075*
H37B0.1045 (17)0.468 (6)0.500 (4)0.075*
H39A0.1349 (17)0.815 (6)0.412 (4)0.075*
H39B0.1499 (17)0.809 (5)0.524 (3)0.075*
H38A0.1081 (18)0.612 (5)0.386 (4)0.075*
H38B0.1571 (18)0.593 (6)0.459 (4)0.075*
H230.2841 (18)0.901 (5)1.239 (3)0.075*
H320.0444 (18)0.430 (5)0.731 (4)0.075*
H18A0.1193 (15)1.160 (6)0.599 (2)0.075*
H18B0.1505 (9)1.260 (2)0.6666 (19)0.075*
H9O0.08200.51100.92330.075*
H13O0.25050.39350.03170.075*
H11O0.17790.31940.93820.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.01931 (19)0.0268 (2)0.0233 (2)0.00009 (16)0.00540 (15)0.00255 (16)
S10.0235 (2)0.0305 (3)0.0230 (2)0.0076 (2)0.00733 (19)0.0031 (2)
S20.0220 (2)0.0288 (3)0.0264 (3)0.00028 (19)0.00589 (19)0.0027 (2)
C220.0242 (10)0.0261 (10)0.0321 (11)0.0036 (8)0.0020 (9)0.0010 (9)
C240.0290 (11)0.0355 (12)0.0395 (13)0.0081 (10)0.0049 (10)0.0137 (10)
C290.0237 (10)0.0266 (11)0.0304 (11)0.0043 (8)0.0049 (8)0.0030 (9)
O60.0779 (16)0.103 (2)0.0373 (11)0.0177 (16)0.0185 (11)0.0065 (13)
C280.0318 (12)0.0430 (14)0.0282 (11)0.0078 (11)0.0058 (9)0.0032 (10)
C270.0376 (12)0.0494 (15)0.0301 (11)0.0125 (12)0.0053 (10)0.0089 (11)
C230.0250 (11)0.0272 (11)0.0427 (14)0.0037 (9)0.0025 (10)0.0046 (10)
N40.0239 (9)0.0311 (10)0.0346 (10)0.0013 (8)0.0038 (8)0.0028 (8)
N50.0235 (9)0.0320 (10)0.0267 (9)0.0028 (8)0.0051 (7)0.0011 (8)
C210.0238 (10)0.0273 (11)0.0276 (10)0.0007 (8)0.0037 (8)0.0013 (8)
O50.0229 (7)0.0299 (8)0.0277 (7)0.0006 (6)0.0046 (6)0.0017 (6)
N60.0393 (12)0.0349 (11)0.0398 (12)0.0025 (9)0.0224 (10)0.0042 (9)
C350.0273 (10)0.0258 (10)0.0337 (12)0.0052 (9)0.0110 (9)0.0034 (9)
C310.0310 (11)0.0267 (11)0.0324 (11)0.0066 (9)0.0131 (9)0.0020 (9)
C300.0305 (11)0.0331 (13)0.0330 (12)0.0082 (9)0.0122 (10)0.0043 (9)
C340.0305 (11)0.0258 (11)0.0342 (12)0.0050 (9)0.0148 (10)0.0011 (9)
C320.0396 (14)0.0366 (14)0.0495 (16)0.0079 (11)0.0231 (12)0.0099 (12)
C330.0339 (12)0.0306 (12)0.0397 (13)0.0001 (10)0.0155 (10)0.0074 (10)
C360.0341 (12)0.0487 (17)0.0323 (11)0.0063 (11)0.0120 (10)0.0004 (11)
O70.0332 (9)0.0443 (11)0.0277 (8)0.0024 (8)0.0105 (7)0.0003 (7)
C390.0407 (14)0.0462 (16)0.0291 (12)0.0025 (12)0.0100 (10)0.0004 (11)
C380.0401 (14)0.0454 (16)0.0293 (12)0.0027 (12)0.0117 (11)0.0020 (11)
C370.0399 (13)0.0370 (14)0.0314 (12)0.0026 (11)0.0093 (11)0.0044 (10)
O80.0417 (10)0.0387 (11)0.0355 (9)0.0009 (8)0.0100 (8)0.0052 (8)
C400.065 (2)0.0461 (19)0.074 (3)0.0002 (17)0.0115 (19)0.0177 (18)
C150.0544 (16)0.0290 (12)0.0285 (12)0.0158 (11)0.0138 (11)0.0032 (9)
C180.0569 (17)0.0321 (14)0.0485 (15)0.0184 (13)0.0223 (14)0.0042 (12)
C110.0614 (17)0.0306 (13)0.0302 (12)0.0188 (12)0.0187 (12)0.0033 (10)
C190.0478 (17)0.0427 (17)0.068 (2)0.0159 (14)0.0070 (16)0.0184 (16)
O90.0407 (10)0.0277 (8)0.0368 (9)0.0049 (7)0.0206 (8)0.0051 (7)
C410.0440 (14)0.0292 (12)0.0432 (14)0.0059 (11)0.0188 (12)0.0051 (11)
C100.0406 (13)0.0306 (12)0.0235 (10)0.0100 (10)0.0052 (9)0.0014 (9)
C160.0440 (14)0.0281 (12)0.0449 (14)0.0094 (11)0.0179 (12)0.0039 (11)
O110.0514 (14)0.0664 (19)0.082 (2)0.0008 (13)0.0094 (14)0.0150 (15)
C430.071 (3)0.057 (2)0.125 (5)0.001 (2)0.019 (3)0.002 (3)
O10.0226 (7)0.0383 (9)0.0225 (7)0.0035 (7)0.0064 (6)0.0020 (7)
N10.0301 (10)0.0244 (10)0.0479 (13)0.0038 (8)0.0128 (9)0.0040 (9)
C10.0240 (10)0.0254 (10)0.0264 (10)0.0036 (8)0.0048 (8)0.0023 (8)
N20.0245 (9)0.0320 (10)0.0288 (9)0.0082 (8)0.0070 (7)0.0006 (8)
C90.0274 (11)0.0268 (11)0.0319 (11)0.0048 (9)0.0042 (9)0.0048 (9)
C20.0318 (12)0.0213 (11)0.0527 (15)0.0025 (9)0.0090 (11)0.0011 (10)
C80.0294 (12)0.0397 (14)0.0454 (14)0.0088 (11)0.0107 (11)0.0031 (12)
C30.0461 (17)0.0269 (14)0.109 (3)0.0081 (12)0.0287 (19)0.0197 (16)
O20.0447 (12)0.0476 (13)0.109 (2)0.0223 (11)0.0254 (13)0.0009 (14)
O130.0382 (10)0.0593 (14)0.0489 (12)0.0150 (10)0.0092 (9)0.0146 (11)
C450.0547 (19)0.069 (2)0.0448 (17)0.0287 (18)0.0067 (15)0.0058 (16)
C170.042 (5)0.032 (4)0.056 (5)0.016 (4)0.027 (4)0.013 (3)
O30.028 (4)0.026 (3)0.041 (4)0.009 (3)0.017 (3)0.004 (2)
C140.033 (4)0.023 (4)0.029 (4)0.005 (3)0.010 (3)0.001 (3)
C130.044 (4)0.031 (3)0.046 (4)0.016 (3)0.024 (4)0.014 (3)
C120.049 (5)0.035 (3)0.041 (4)0.011 (3)0.024 (4)0.013 (3)
N30.035 (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)
C420.053 (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)
O100.0381 (9)0.0338 (10)0.0434 (10)0.0013 (8)0.0152 (8)0.0095 (8)
C200.049 (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)
C250.0367 (13)0.0509 (16)0.0636 (17)0.0134 (12)0.0236 (12)0.0291 (13)
C260.071 (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)
C70.0332 (12)0.0318 (13)0.076 (2)0.0101 (11)0.0124 (13)0.0104 (13)
C40.0421 (15)0.0216 (12)0.107 (3)0.0102 (11)0.0180 (16)0.0034 (14)
C60.059 (2)0.0428 (18)0.131 (3)0.0227 (16)0.026 (2)0.003 (2)
C50.053 (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)
C440.072 (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)
O120.0686 (18)0.083 (2)0.0690 (18)0.0034 (16)0.0266 (15)0.0075 (16)
O40.0377 (11)0.0375 (12)0.106 (2)0.0024 (10)0.0192 (13)0.0023 (13)
Geometric parameters (Å, º) top
Ca1—O102.362 (2)C43—H43C0.9800
Ca1—O52.3920 (18)O1—Ca1i2.4814 (17)
Ca1—O92.3986 (19)N1—C11.327 (3)
Ca1—O12.4225 (19)N1—C21.388 (3)
Ca1—O1i2.4814 (17)C1—N21.345 (3)
Ca1—N2i2.507 (2)N2—C91.386 (3)
Ca1—N52.516 (2)N2—Ca1i2.507 (2)
S1—O11.5277 (17)C9—C21.409 (4)
S1—C11.771 (2)C9—C81.411 (4)
S1—C101.820 (3)C2—C31.406 (4)
S2—O51.5129 (17)C8—C71.382 (4)
S2—C211.775 (2)C8—H80.9500
S2—C301.832 (3)C3—C41.383 (5)
C22—N41.385 (3)C3—H30.9500
C22—C231.409 (3)O2—C71.385 (4)
C22—C291.415 (4)O2—C61.455 (6)
C24—C231.372 (5)O13—C451.419 (4)
C24—C271.403 (5)O13—H13O0.9194
C24—C25'1.448 (4)C45—H45A0.9800
C24—C251.448 (4)C45—H45B0.9800
C29—N51.386 (3)C45—H45C0.9800
C29—C281.405 (4)C17—O31.448 (15)
O6—C271.426 (4)C17—H17A0.9900
O6—C26'1.504 (11)C17—H17B0.9900
O6—C261.533 (8)O3—C141.362 (14)
C28—C271.380 (4)C14—C131.387 (12)
C28—H281.02 (5)C13—C121.379 (9)
C23—H230.95 (5)C13—H130.9500
N4—C211.331 (3)C12—N31.334 (10)
N5—C211.339 (3)C12—H120.9500
N6—C321.327 (4)O3'—C14'1.326 (17)
N6—C311.350 (3)O3'—C17'1.457 (16)
C35—C311.395 (3)C17'—H17C0.9900
C35—C341.406 (4)C17'—H17D0.9900
C35—C361.505 (4)C14'—C13'1.397 (15)
C31—C301.494 (4)C13'—C12'1.370 (10)
C30—H30A0.98 (6)C13'—H13'0.9500
C30—H30B0.90 (5)C12'—N3'1.347 (11)
C34—O71.352 (3)C12'—H12'0.9500
C34—C331.388 (4)C42—O101.471 (9)
C32—C331.383 (4)C42—H42A0.9800
C32—H321.00 (5)C42—H42B0.9800
C33—H330.92 (3)C42—H42C0.9800
C36—H36A0.9800C42'—O101.327 (14)
C36—H36B0.9800C42'—H42D0.9800
C36—H36C0.9800C42'—H42E0.9800
O7—C371.442 (3)C42'—H42F0.9800
C39—O81.419 (4)O10—H10O0.8611
C39—C381.514 (4)C20—O41.471 (9)
C39—H39A0.98 (5)C20—H20A0.9800
C39—H39B1.07 (5)C20—H20B0.9800
C38—C371.516 (4)C20—H20C0.9800
C38—H38A0.94 (6)C20'—O41.423 (8)
C38—H38B1.02 (6)C20'—H20D0.9800
C37—H37A1.02 (3)C20'—H20E0.9800
C37—H37B0.98 (6)C20'—H20F0.9800
O8—C401.404 (5)C25—C261.595 (11)
C40—H40A0.9800C25—H25A0.9900
C40—H40B0.9800C25—H25B0.9900
C40—H40C0.9800C26—H26A0.9900
C15—C111.397 (4)C26—H26B0.9900
C15—C14'1.416 (12)C25'—C26'1.608 (12)
C15—C141.438 (10)C25'—H25C0.9900
C15—C161.494 (4)C25'—H25D0.9900
C18—C171.468 (11)C26'—H26C0.9900
C18—C191.500 (6)C26'—H26D0.9900
C18—C17'1.620 (13)C7—C41.396 (6)
C18—H18A0.98 (3)C4—C5'1.505 (11)
C18—H18B1.03 (2)C4—C51.526 (9)
C11—N31.313 (9)C6—C5'1.475 (14)
C11—N3'1.443 (12)C6—C51.558 (11)
C11—C101.508 (4)C6—H6A0.9900
C19—O41.391 (6)C6—H6B0.9900
C19—H19A0.9900C6—H6C0.9900
C19—H19B0.9900C6—H6D0.9900
O9—C411.425 (3)C5—H5A0.9900
O9—H9O0.8781C5—H5B0.9900
C41—H41A0.9800C5'—H5'10.9900
C41—H41B0.9800C5'—H5'20.9900
C41—H41C0.9800C44—O121.363 (13)
C10—H10A0.95 (3)C44—H44A0.9800
C10—H10B0.97 (3)C44—H44B0.9800
C16—H16A0.9800C44—H44C0.9800
C16—H16B0.9800C44'—O121.422 (12)
C16—H16C0.9800C44'—H44D0.9800
O11—C431.375 (7)C44'—H44E0.9800
O11—H11O0.9436C44'—H44F0.9800
C43—H43A0.9800O12—H12O0.97 (3)
C43—H43B0.9800
O10—Ca1—O590.98 (7)S1—O1—Ca1i121.60 (9)
O10—Ca1—O9168.52 (7)Ca1—O1—Ca1i113.45 (6)
O5—Ca1—O977.75 (6)C1—N1—C2101.4 (2)
O10—Ca1—O196.45 (7)N1—C1—N2119.6 (2)
O5—Ca1—O176.76 (6)N1—C1—S1121.54 (19)
O9—Ca1—O178.99 (7)N2—C1—S1118.86 (18)
O10—Ca1—O1i75.94 (7)C1—N2—C9101.2 (2)
O5—Ca1—O1i138.91 (6)C1—N2—Ca1i119.07 (15)
O9—Ca1—O1i111.19 (7)C9—N2—Ca1i134.66 (17)
O1—Ca1—O1i66.55 (6)N2—C9—C2108.9 (2)
O10—Ca1—N2i107.48 (8)N2—C9—C8129.0 (3)
O5—Ca1—N2i150.00 (6)C2—C9—C8122.1 (2)
O9—Ca1—N2i83.71 (7)N1—C2—C3129.4 (3)
O1—Ca1—N2i122.66 (7)N1—C2—C9109.0 (2)
O1i—Ca1—N2i70.05 (6)C3—C2—C9121.6 (3)
O10—Ca1—N581.59 (7)C7—C8—C9114.7 (3)
O5—Ca1—N571.23 (7)C7—C8—H8122.6
O9—Ca1—N596.61 (7)C9—C8—H8122.6
O1—Ca1—N5147.87 (7)C4—C3—C2116.0 (3)
O1i—Ca1—N5141.54 (6)C4—C3—H3122.0
N2i—Ca1—N587.92 (7)C2—C3—H3122.0
O1—S1—C1103.16 (11)C7—O2—C6106.6 (3)
O1—S1—C10103.43 (12)C45—O13—H13O108.3
C1—S1—C1098.41 (12)O13—C45—H45A109.5
O5—S2—C21104.69 (11)O13—C45—H45B109.5
O5—S2—C30106.03 (12)H45A—C45—H45B109.5
C21—S2—C3095.02 (12)O13—C45—H45C109.5
N4—C22—C23129.3 (3)H45A—C45—H45C109.5
N4—C22—C29108.8 (2)H45B—C45—H45C109.5
C23—C22—C29121.8 (3)O3—C17—C18106.5 (8)
C23—C24—C27122.4 (2)O3—C17—H17A110.4
C23—C24—C25'126.8 (3)C18—C17—H17A110.4
C27—C24—C25'110.7 (3)O3—C17—H17B110.4
C23—C24—C25126.8 (3)C18—C17—H17B110.4
C27—C24—C25110.7 (3)H17A—C17—H17B108.6
N5—C29—C28129.7 (2)C14—O3—C17117.8 (10)
N5—C29—C22108.7 (2)O3—C14—C13123.2 (9)
C28—C29—C22121.6 (2)O3—C14—C15119.0 (9)
C27—O6—C26'99.0 (5)C13—C14—C15117.7 (7)
C27—O6—C26102.4 (4)C12—C13—C14117.2 (6)
C27—C28—C29115.3 (3)C12—C13—H13121.4
C27—C28—H28124 (3)C14—C13—H13121.4
C29—C28—H28120 (3)N3—C12—C13125.0 (6)
C28—C27—C24123.2 (3)N3—C12—H12117.5
C28—C27—O6123.5 (3)C13—C12—H12117.5
C24—C27—O6113.3 (3)C11—N3—C12119.5 (6)
C24—C23—C22115.7 (3)C14'—O3'—C17'116.4 (11)
C24—C23—H23122 (3)O3'—C17'—C18105.9 (8)
C22—C23—H23123 (3)O3'—C17'—H17C110.6
C21—N4—C22101.6 (2)C18—C17'—H17C110.6
C21—N5—C29101.5 (2)O3'—C17'—H17D110.6
C21—N5—Ca1117.86 (15)C18—C17'—H17D110.6
C29—N5—Ca1139.01 (16)H17C—C17'—H17D108.7
N4—C21—N5119.5 (2)O3'—C14'—C13'125.4 (10)
N4—C21—S2121.55 (19)O3'—C14'—C15111.0 (10)
N5—C21—S2118.98 (17)C13'—C14'—C15123.2 (9)
S2—O5—Ca1123.69 (10)C12'—C13'—C14'119.0 (7)
C32—N6—C31117.2 (2)C12'—C13'—H13'120.5
C31—C35—C34117.0 (2)C14'—C13'—H13'120.5
C31—C35—C36122.2 (2)N3'—C12'—C13'123.8 (7)
C34—C35—C36120.7 (2)N3'—C12'—H12'118.1
N6—C31—C35123.6 (2)C13'—C12'—H12'118.1
N6—C31—C30114.7 (2)C12'—N3'—C11114.0 (8)
C35—C31—C30121.6 (2)O10—C42—H42A109.5
C31—C30—S2109.58 (17)O10—C42—H42B109.5
C31—C30—H30A110 (3)H42A—C42—H42B109.5
S2—C30—H30A107 (3)O10—C42—H42C109.5
C31—C30—H30B109 (3)H42A—C42—H42C109.5
S2—C30—H30B109 (4)H42B—C42—H42C109.5
H30A—C30—H30B113 (5)O10—C42'—H42D109.5
O7—C34—C33124.9 (2)O10—C42'—H42E109.5
O7—C34—C35115.2 (2)H42D—C42'—H42E109.5
C33—C34—C35119.8 (2)O10—C42'—H42F109.5
N6—C32—C33124.6 (3)H42D—C42'—H42F109.5
N6—C32—H32115 (3)H42E—C42'—H42F109.5
C33—C32—H32120 (3)C42'—O10—Ca1137.4 (7)
C32—C33—C34117.7 (3)C42—O10—Ca1128.0 (4)
C32—C33—H33117 (3)C42'—O10—H10O96.8
C34—C33—H33125 (3)C42—O10—H10O111.8
C35—C36—H36A109.5Ca1—O10—H10O120.2
C35—C36—H36B109.5O4—C20—H20A109.5
H36A—C36—H36B109.5O4—C20—H20B109.5
C35—C36—H36C109.5H20A—C20—H20B109.5
H36A—C36—H36C109.5O4—C20—H20C109.5
H36B—C36—H36C109.5H20A—C20—H20C109.5
C34—O7—C37118.6 (2)H20B—C20—H20C109.5
O8—C39—C38108.7 (3)O4—C20'—H20D109.5
O8—C39—H39A109 (3)O4—C20'—H20E109.5
C38—C39—H39A109 (3)H20D—C20'—H20E109.5
O8—C39—H39B104 (3)O4—C20'—H20F109.5
C38—C39—H39B118 (3)H20D—C20'—H20F109.5
H39A—C39—H39B108 (4)H20E—C20'—H20F109.5
C39—C38—C37112.5 (2)C24—C25—C26101.1 (4)
C39—C38—H38A110 (3)C24—C25—H25A111.6
C37—C38—H38A107 (3)C26—C25—H25A111.6
C39—C38—H38B113 (3)C24—C25—H25B111.6
C37—C38—H38B105 (3)C26—C25—H25B111.6
H38A—C38—H38B109 (4)H25A—C25—H25B109.4
O7—C37—C38106.7 (2)O6—C26—C25105.0 (4)
O7—C37—H37A110 (3)O6—C26—H26A110.8
C38—C37—H37A112 (3)C25—C26—H26A110.8
O7—C37—H37B111 (3)O6—C26—H26B110.8
C38—C37—H37B116 (3)C25—C26—H26B110.8
H37A—C37—H37B100 (4)H26A—C26—H26B108.8
C40—O8—C39111.6 (3)C24—C25'—C26'97.4 (4)
O8—C40—H40A109.5C24—C25'—H25C112.3
O8—C40—H40B109.5C26'—C25'—H25C112.3
H40A—C40—H40B109.5C24—C25'—H25D112.3
O8—C40—H40C109.5C26'—C25'—H25D112.3
H40A—C40—H40C109.5H25C—C25'—H25D109.9
H40B—C40—H40C109.5O6—C26'—C25'105.7 (6)
C11—C15—C14'111.9 (6)O6—C26'—H26C110.6
C11—C15—C14119.6 (5)C25'—C26'—H26C110.6
C11—C15—C16123.0 (2)O6—C26'—H26D110.6
C14'—C15—C16124.1 (6)C25'—C26'—H26D110.6
C14—C15—C16116.7 (5)H26C—C26'—H26D108.7
C17—C18—C19103.8 (6)C8—C7—O2123.5 (3)
C19—C18—C17'123.5 (6)C8—C7—C4123.7 (3)
C17—C18—H18A121 (3)O2—C7—C4112.7 (3)
C19—C18—H18A109 (3)C3—C4—C7121.9 (3)
C17'—C18—H18A104 (3)C3—C4—C5'131.3 (6)
C17—C18—H18B108.1 (16)C7—C4—C5'105.3 (6)
C19—C18—H18B111.0 (15)C3—C4—C5127.4 (5)
C17'—C18—H18B103.9 (16)C7—C4—C5110.0 (4)
H18A—C18—H18B104 (4)O2—C6—C5'107.4 (5)
N3—C11—C15120.8 (4)O2—C6—C5109.6 (4)
C15—C11—N3'127.0 (4)O2—C6—H6A109.8
N3—C11—C10116.5 (4)C5—C6—H6A109.8
C15—C11—C10121.4 (3)O2—C6—H6B109.8
N3'—C11—C10110.6 (5)C5—C6—H6B109.8
O4—C19—C18109.6 (3)H6A—C6—H6B108.2
O4—C19—H19A109.8O2—C6—H6C110.2
C18—C19—H19A109.8C5'—C6—H6C110.2
O4—C19—H19B109.8O2—C6—H6D110.2
C18—C19—H19B109.8C5'—C6—H6D110.2
H19A—C19—H19B108.2H6C—C6—H6D108.5
C41—O9—Ca1131.18 (16)C4—C5—C699.0 (6)
C41—O9—H9O109.8C4—C5—H5A112.0
Ca1—O9—H9O117.6C6—C5—H5A112.0
O9—C41—H41A109.5C4—C5—H5B112.0
O9—C41—H41B109.5C6—C5—H5B112.0
H41A—C41—H41B109.5H5A—C5—H5B109.7
O9—C41—H41C109.5C6—C5'—C4103.7 (8)
H41A—C41—H41C109.5C6—C5'—H5'1111.0
H41B—C41—H41C109.5C4—C5'—H5'1111.0
C11—C10—S1109.81 (19)C6—C5'—H5'2111.0
C11—C10—H10A111 (3)C4—C5'—H5'2111.0
S1—C10—H10A107 (3)H5'1—C5'—H5'2109.0
C11—C10—H10B110 (3)O12—C44—H44A109.5
S1—C10—H10B109 (3)O12—C44—H44B109.5
H10A—C10—H10B109 (4)H44A—C44—H44B109.5
C15—C16—H16A109.5O12—C44—H44C109.5
C15—C16—H16B109.5H44A—C44—H44C109.5
H16A—C16—H16B109.5H44B—C44—H44C109.5
C15—C16—H16C109.5O12—C44'—H44D109.5
H16A—C16—H16C109.5O12—C44'—H44E109.5
H16B—C16—H16C109.5H44D—C44'—H44E109.5
C43—O11—H11O115.4O12—C44'—H44F109.5
O11—C43—H43A109.5H44D—C44'—H44F109.5
O11—C43—H43B109.5H44E—C44'—H44F109.5
H43A—C43—H43B109.5C44—O12—H12O114 (4)
O11—C43—H43C109.5C44'—O12—H12O112 (4)
H43A—C43—H43C109.5C19—O4—C20'126.3 (8)
H43B—C43—H43C109.5C19—O4—C2096.2 (8)
S1—O1—Ca1120.64 (9)
N4—C22—C29—N51.0 (3)C2—N1—C1—N20.2 (3)
C23—C22—C29—N5179.1 (2)C2—N1—C1—S1177.61 (19)
N4—C22—C29—C28178.2 (2)O1—S1—C1—N1148.4 (2)
C23—C22—C29—C280.1 (4)C10—S1—C1—N1105.6 (2)
N5—C29—C28—C27178.2 (3)O1—S1—C1—N229.1 (2)
C22—C29—C28—C270.8 (4)C10—S1—C1—N276.9 (2)
C29—C28—C27—C240.4 (4)N1—C1—N2—C90.0 (3)
C29—C28—C27—O6180.0 (3)S1—C1—N2—C9177.53 (17)
C23—C24—C27—C280.6 (5)N1—C1—N2—Ca1i158.33 (18)
C25'—C24—C27—C28178.4 (3)S1—C1—N2—Ca1i19.2 (2)
C25—C24—C27—C28178.4 (3)C1—N2—C9—C20.1 (3)
C23—C24—C27—O6179.0 (3)Ca1i—N2—C9—C2153.2 (2)
C25'—C24—C27—O61.9 (4)C1—N2—C9—C8179.1 (3)
C25—C24—C27—O61.9 (4)Ca1i—N2—C9—C826.1 (4)
C26'—O6—C27—C28156.2 (5)C1—N1—C2—C3178.1 (4)
C26—O6—C27—C28164.1 (4)C1—N1—C2—C90.2 (3)
C26'—O6—C27—C2424.2 (5)N2—C9—C2—N10.2 (3)
C26—O6—C27—C2415.5 (5)C8—C9—C2—N1179.1 (2)
C27—C24—C23—C221.3 (4)N2—C9—C2—C3178.3 (3)
C25'—C24—C23—C22177.6 (3)C8—C9—C2—C31.1 (5)
C25—C24—C23—C22177.6 (3)N2—C9—C8—C7178.0 (3)
N4—C22—C23—C24176.8 (3)C2—C9—C8—C71.2 (4)
C29—C22—C23—C240.9 (4)N1—C2—C3—C4177.1 (3)
C23—C22—N4—C21178.6 (3)C9—C2—C3—C40.5 (6)
C29—C22—N4—C210.6 (3)C19—C18—C17—O373.5 (7)
C28—C29—N5—C21178.2 (3)C18—C17—O3—C14162.9 (8)
C22—C29—N5—C210.8 (3)C17—O3—C14—C139.1 (12)
C28—C29—N5—Ca114.5 (4)C17—O3—C14—C15166.7 (8)
C22—C29—N5—Ca1164.62 (19)C11—C15—C14—O3177.3 (6)
C22—N4—C21—N50.1 (3)C16—C15—C14—O312.0 (9)
C22—N4—C21—S2178.21 (18)C11—C15—C14—C131.3 (9)
C29—N5—C21—N40.5 (3)C16—C15—C14—C13172.0 (6)
Ca1—N5—C21—N4168.51 (18)O3—C14—C13—C12179.9 (8)
C29—N5—C21—S2178.83 (18)C15—C14—C13—C124.1 (12)
Ca1—N5—C21—S213.1 (3)C14—C13—C12—N32.0 (14)
O5—S2—C21—N4161.4 (2)C15—C11—N3—C126.3 (10)
C30—S2—C21—N490.6 (2)C10—C11—N3—C12173.4 (6)
O5—S2—C21—N520.3 (2)C13—C12—N3—C113.4 (13)
C30—S2—C21—N587.7 (2)C14'—O3'—C17'—C18179.7 (8)
C21—S2—O5—Ca119.16 (15)C19—C18—C17'—O3'58.0 (9)
C30—S2—O5—Ca180.59 (13)C17'—O3'—C14'—C13'6.5 (15)
C32—N6—C31—C350.7 (4)C17'—O3'—C14'—C15178.9 (8)
C32—N6—C31—C30177.1 (2)C11—C15—C14'—O3'179.7 (7)
C34—C35—C31—N61.0 (4)C16—C15—C14'—O3'11.3 (11)
C36—C35—C31—N6178.6 (3)C11—C15—C14'—C13'7.1 (11)
C34—C35—C31—C30176.7 (2)C16—C15—C14'—C13'176.1 (7)
C36—C35—C31—C301.0 (4)O3'—C14'—C13'—C12'179.0 (10)
N6—C31—C30—S289.6 (2)C15—C14'—C13'—C12'7.5 (14)
C35—C31—C30—S288.2 (3)C14'—C13'—C12'—N3'1.5 (15)
O5—S2—C30—C3164.2 (2)C13'—C12'—N3'—C118.9 (13)
C21—S2—C30—C31171.04 (19)C15—C11—N3'—C12'9.1 (9)
C31—C35—C34—O7178.5 (2)C10—C11—N3'—C12'177.6 (6)
C36—C35—C34—O70.9 (3)C23—C24—C25—C26163.4 (4)
C31—C35—C34—C330.9 (4)C27—C24—C25—C2617.6 (4)
C36—C35—C34—C33178.6 (2)C27—O6—C26—C2525.3 (5)
C31—N6—C32—C330.3 (4)C24—C25—C26—O626.3 (5)
N6—C32—C33—C340.3 (5)C23—C24—C25'—C26'159.3 (5)
O7—C34—C33—C32178.8 (3)C27—C24—C25'—C26'19.7 (5)
C35—C34—C33—C320.6 (4)C27—O6—C26'—C25'35.5 (6)
C33—C34—O7—C375.1 (4)C24—C25'—C26'—O634.5 (6)
C35—C34—O7—C37174.3 (2)C9—C8—C7—O2179.1 (3)
O8—C39—C38—C3751.8 (3)C9—C8—C7—C40.2 (5)
C34—O7—C37—C38165.9 (2)C6—O2—C7—C8177.4 (4)
C39—C38—C37—O758.3 (3)C6—O2—C7—C43.3 (5)
C38—C39—O8—C40175.0 (3)C2—C3—C4—C71.8 (6)
C14—C15—C11—N34.0 (6)C2—C3—C4—C5'162.0 (9)
C16—C15—C11—N3166.1 (6)C2—C3—C4—C5171.2 (6)
C14'—C15—C11—N3'1.3 (7)C8—C7—C4—C31.8 (6)
C16—C15—C11—N3'167.8 (6)O2—C7—C4—C3177.6 (4)
C14'—C15—C11—C10168.8 (6)C8—C7—C4—C5'165.7 (7)
C14—C15—C11—C10170.5 (6)O2—C7—C4—C5'15.0 (7)
C16—C15—C11—C100.4 (5)C8—C7—C4—C5172.8 (5)
C17—C18—C19—O4173.9 (5)O2—C7—C4—C56.5 (7)
C17'—C18—C19—O4165.7 (5)C7—O2—C6—C5'10.2 (8)
N3—C11—C10—S180.3 (6)C7—O2—C6—C511.6 (7)
C15—C11—C10—S186.7 (3)C3—C4—C5—C6177.2 (5)
N3'—C11—C10—S1104.0 (5)C7—C4—C5—C612.3 (7)
O1—S1—C10—C1168.0 (2)O2—C6—C5—C414.3 (8)
C1—S1—C10—C11173.7 (2)O2—C6—C5'—C418.5 (11)
C1—S1—O1—Ca1128.47 (12)C3—C4—C5'—C6174.2 (6)
C10—S1—O1—Ca1129.39 (13)C7—C4—C5'—C620.1 (10)
C1—S1—O1—Ca1i26.68 (14)C18—C19—O4—C20'178.1 (6)
C10—S1—O1—Ca1i75.46 (14)C18—C19—O4—C20169.9 (5)
Symmetry code: (i) x, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O11ii0.992.523.285 (12)134
C13—H13···O11ii0.952.603.451 (9)150
C17—H17C···O11ii0.992.543.527 (12)177
O10—H10O···N3i0.861.922.780 (8)176
O10—H10O···N3i0.861.812.654 (10)167
C26—H26A···O4iii0.992.433.137 (8)128
C25—H25C···O7iv0.992.433.341 (5)152
C25—H25D···O4iii0.992.633.301 (4)125
O12—H12O···N1v0.97 (3)1.89 (3)2.853 (4)171 (6)
C10—H10A···O8v0.95 (3)2.35 (4)3.092 (3)135 (4)
C30—H30B···O13vi0.90 (5)2.55 (6)2.998 (3)112 (4)
C32—H32···O12v1.00 (5)2.54 (5)3.260 (5)128 (4)
O9—H9O···N60.881.902.774 (3)178
O13—H13O···N4vii0.921.812.721 (3)170
O11—H11O···O13vi0.941.892.767 (4)153
C16—H16B···O30.982.312.785 (11)109
C19—H19B···O30.992.412.813 (11)104
C36—H36B···O70.982.282.753 (3)108
Symmetry codes: (i) x, y, z+2; (ii) x, y+1, z; (iii) x+1/2, y1/2, 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, y1/2, z+1.
 

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