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Apremilast (APR), an anti-psoriatic agent, easily forms isostructural cocrystals and solvates with aromatic entities, often disobeying at the same time Kitaigorodsky's rule as to the saturation of possible hydrogen-bonding sites. In this paper the reasons for this peculiar behavior are investigated, employing a joint experimental and theoretical approach. This includes the design of cocrystals with coformers having a high propensity towards the formation of both aromatic–aromatic and hydrogen-bonding interactions, determination of their structure, using solid-state NMR spectroscopy and X-ray crystallography, as well as calculations of stabilization energies of formation of the obtained cocrystals, followed by crystal structure prediction calculations and solubility measurements. The findings indicate that the stabilization energies of cocrystal formation are positive in all cases, which results from strain in the APR conformation in these crystal forms. On the other hand, solubility measurements show that the Gibbs free energy of formation of the apremilast:picolinamide cocrystal is negative, suggesting that the formation of the studied cocrystals is entropy driven. This entropic stabilization is associated with the disorder observed in almost all known cocrystals and solvates of APR.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061900917X/xk5057sup1.cif
Contains datablocks apre1, cocr1l, cocr2l, cocr3lf, cocr4lf

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S205252061900917X/xk5057sup2.pdf
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061900917X/xk5057apre1sup3.hkl
Contains datablock apre1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061900917X/xk5057cocr1lsup4.hkl
Contains datablock cocr1l

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061900917X/xk5057cocr2lsup5.hkl
Contains datablock cocr2l

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061900917X/xk5057cocr3lfsup6.hkl
Contains datablock cocr3lf

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205252061900917X/xk5057cocr4lfsup7.hkl
Contains datablock cocr4lf

CCDC references: 1916487; 1916491; 1916488; 1916489; 1916490

Computing details top

For all structures, data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32); cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32); data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(apre1) top
Crystal data top
C22H24N2O7SF(000) = 1936
Mr = 460.49Dx = 1.360 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 8.71353 (13) ÅCell parameters from 14995 reflections
b = 29.4960 (6) Åθ = 2.9–74.2°
c = 17.6717 (2) ŵ = 1.68 mm1
β = 97.9370 (14)°T = 293 K
V = 4498.36 (12) Å30.31 × 0.06 × 0.02 mm
Z = 8
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
17606 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source14660 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.038
Detector resolution: 4.1685 pixels mm-1θmax = 75.4°, θmin = 2.5°
ω scansh = 910
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 3636
Tmin = 0.817, Tmax = 1.000l = 2222
43359 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.3705P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.17 e Å3
17606 reflectionsΔρmin = 0.30 e Å3
1169 parametersAbsolute structure: Flack x determined using 5723 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraintAbsolute structure parameter: 0.004 (8)
Primary atom site location: structure-invariant direct methods
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*/Ueq
S1A1.13126 (12)0.24313 (4)0.33826 (6)0.0605 (3)
O1A0.7488 (4)0.15813 (13)0.3638 (2)0.0759 (9)
O2A1.1061 (4)0.21159 (11)0.55654 (16)0.0576 (7)
O3A1.3046 (7)0.06551 (18)0.7028 (3)0.1191 (18)
O4A1.2683 (4)0.26942 (18)0.3397 (2)0.0917 (12)
O5A1.1468 (6)0.19552 (15)0.3507 (3)0.0964 (13)
O6A0.7826 (3)0.34366 (12)0.63702 (18)0.0639 (8)
O7A0.4883 (3)0.32723 (12)0.6093 (2)0.0667 (8)
N1A0.9157 (4)0.19633 (11)0.45461 (18)0.0486 (7)
N2A1.2048 (5)0.12631 (15)0.6355 (2)0.0651 (10)
H2A1.21250.15530.63310.078*
C1A1.0956 (5)0.10711 (15)0.5807 (3)0.0564 (10)
C2A1.0580 (7)0.06036 (17)0.5742 (4)0.0740 (14)
H2AA1.10980.03980.60850.089*
C3A0.9450 (6)0.04523 (18)0.5172 (4)0.0768 (15)
H3A0.92080.01450.51540.092*
C4A0.8663 (6)0.07344 (17)0.4629 (3)0.0690 (12)
H4A0.79130.06250.42470.083*
C5A1.0138 (4)0.13529 (14)0.5259 (2)0.0498 (8)
C6A1.0222 (4)0.18512 (13)0.5178 (2)0.0468 (8)
C7A0.9051 (5)0.11878 (15)0.4685 (3)0.0544 (9)
C8A0.8427 (5)0.15768 (16)0.4209 (2)0.0554 (9)
C9A1.3031 (7)0.1060 (2)0.6935 (3)0.0787 (16)
C10A1.4047 (7)0.1378 (3)0.7433 (3)0.0933 (19)
H10A1.35150.14800.78420.140*
H10B1.42950.16340.71370.140*
H10C1.49840.12250.76400.140*
C11A0.8818 (4)0.24160 (14)0.4228 (2)0.0504 (8)
H11A0.82090.23710.37250.061*
C12A1.0290 (5)0.26663 (15)0.4090 (2)0.0559 (9)
H12A1.09840.26770.45690.067*
H12B1.00130.29760.39460.067*
C13A1.0119 (8)0.2526 (4)0.2516 (3)0.116 (3)
H13A0.98450.28410.24740.174*
H13B0.91960.23460.24990.174*
H13C1.06620.24420.21000.174*
C14A0.7786 (4)0.26766 (14)0.4704 (2)0.0486 (8)
C15A0.6204 (5)0.26208 (16)0.4531 (3)0.0566 (10)
H15A0.58040.24490.41080.068*
C16A0.5207 (5)0.28176 (16)0.4980 (3)0.0601 (10)
H16A0.41430.27770.48580.072*
C17A0.7373 (5)0.31566 (14)0.5767 (2)0.0506 (8)
C18A0.5782 (5)0.30742 (15)0.5610 (3)0.0541 (9)
C19A0.8370 (4)0.29491 (15)0.5322 (2)0.0519 (9)
H19A0.94340.29920.54380.062*
C20A0.9374 (5)0.36016 (17)0.6488 (3)0.0618 (11)
H20A0.96330.37390.60230.074*
H20B1.00910.33550.66310.074*
C21A0.9478 (7)0.3949 (2)0.7119 (3)0.0870 (17)
H21A0.88130.42000.69570.131*
H21B1.05280.40530.72340.131*
H21C0.91590.38140.75660.131*
C22A0.3295 (6)0.3142 (2)0.6016 (4)0.0872 (18)
H22A0.27360.32890.55770.131*
H22B0.28640.32310.64660.131*
H22C0.32140.28190.59550.131*
S1B0.39251 (15)0.45270 (5)0.62227 (7)0.0751 (3)
O1B0.7444 (4)0.52389 (12)0.59477 (19)0.0718 (9)
O2B0.3537 (4)0.50744 (11)0.39455 (17)0.0612 (7)
O4B0.3924 (7)0.50073 (18)0.6346 (3)0.1180 (18)
O5B0.2629 (4)0.4319 (3)0.5767 (3)0.123 (2)
O6B0.7389 (3)0.34674 (13)0.31471 (18)0.0638 (8)
O7B1.0245 (3)0.37108 (11)0.35207 (19)0.0602 (7)
N1B0.5556 (4)0.50291 (12)0.49455 (19)0.0527 (7)
N2B0.2854 (4)0.60340 (13)0.3564 (2)0.0598 (9)
H2B0.32420.58730.32330.072*
C1B0.3983 (5)0.61156 (15)0.4195 (2)0.0530 (9)
C2B0.4451 (5)0.65444 (16)0.4485 (3)0.0621 (10)
H2BA0.39610.68030.42670.075*
C3B0.5629 (5)0.65877 (16)0.5088 (3)0.0617 (10)
H3B0.59250.68770.52610.074*
C4B0.6391 (5)0.62136 (16)0.5448 (2)0.0573 (10)
H4B0.71880.62460.58520.069*
C5B0.5899 (5)0.57956 (14)0.5172 (2)0.0506 (8)
C7B0.6439 (5)0.53379 (15)0.5434 (2)0.0562 (10)
C8X0.4496 (5)0.52585 (14)0.4421 (2)0.0499 (8)
C8B0.4732 (4)0.57479 (14)0.4561 (2)0.0487 (8)
C9B0.1917 (6)0.63401 (18)0.3141 (3)0.0638 (11)
C10B0.0983 (7)0.6143 (2)0.2446 (3)0.0796 (14)
H10D0.15160.61890.20120.119*
H10E0.00100.62890.23600.119*
H10F0.08440.58240.25210.119*
C11B0.5566 (5)0.45321 (13)0.5003 (2)0.0526 (9)
H11B0.45850.44250.47210.063*
C12B0.5608 (5)0.43727 (15)0.5824 (3)0.0596 (10)
H12C0.65090.45020.61330.072*
H12D0.57160.40450.58410.072*
C13B0.4156 (8)0.4255 (2)0.7115 (3)0.0897 (17)
H13D0.49810.43970.74480.135*
H13E0.44030.39410.70500.135*
H13F0.32110.42770.73350.135*
C14B0.6856 (5)0.43187 (14)0.4624 (2)0.0526 (9)
C15B0.8394 (5)0.44239 (16)0.4858 (3)0.0619 (11)
H15B0.86610.46280.52560.074*
C16B0.9544 (5)0.42233 (16)0.4496 (3)0.0606 (10)
H16B1.05760.42980.46510.073*
C17B0.9180 (5)0.39175 (15)0.3917 (2)0.0513 (9)
C18B0.7640 (5)0.37933 (15)0.3694 (2)0.0508 (9)
C19B0.6489 (4)0.40012 (15)0.4047 (2)0.0510 (9)
H19B0.54570.39260.38940.061*
C20B0.5804 (5)0.33448 (19)0.2868 (3)0.0662 (12)
H20C0.52640.35990.26060.079*
H20D0.52640.32570.32900.079*
C21B0.5862 (7)0.2957 (2)0.2331 (3)0.0856 (17)
H21D0.65210.30330.19580.128*
H21E0.48370.28940.20790.128*
H21F0.62650.26940.26110.128*
C22B1.1824 (5)0.3844 (2)0.3698 (4)0.0782 (15)
H22D1.24400.36800.33800.117*
H22E1.21820.37780.42250.117*
H22F1.19150.41630.36090.117*
S1C0.86399 (12)0.41913 (4)0.11460 (6)0.0619 (3)
O1C1.2674 (5)0.34555 (14)0.1294 (2)0.0844 (11)
O2C0.9242 (4)0.36645 (11)0.08825 (18)0.0669 (8)
O3C0.7233 (6)0.20267 (15)0.1516 (3)0.0949 (12)
O4C0.8627 (6)0.37052 (15)0.1149 (3)0.0969 (14)
O5C0.7203 (4)0.44299 (19)0.1074 (2)0.0958 (14)
O6C1.2105 (3)0.51470 (15)0.18452 (19)0.0741 (10)
O7C1.5047 (3)0.50402 (13)0.1531 (2)0.0713 (9)
N1C1.1071 (4)0.36761 (12)0.0206 (2)0.0561 (8)
N2C0.8401 (5)0.27108 (15)0.1276 (2)0.0682 (10)
H2C0.83880.29870.14350.082*
C1C0.9470 (6)0.26152 (15)0.0633 (3)0.0600 (10)
C2C0.9871 (6)0.21813 (18)0.0355 (3)0.0706 (12)
H2CA0.93980.19300.06060.085*
C3C1.0953 (6)0.21180 (18)0.0281 (3)0.0749 (13)
H3C1.11940.18240.04460.090*
C4C1.1698 (6)0.24770 (18)0.0686 (3)0.0690 (12)
H4C1.24240.24310.11160.083*
C5C1.1299 (5)0.29068 (16)0.0413 (3)0.0598 (10)
C6C1.1819 (5)0.33581 (17)0.0713 (3)0.0629 (11)
C7C1.0079 (5)0.34650 (16)0.0369 (2)0.0550 (9)
C8C1.0226 (5)0.29745 (15)0.0235 (2)0.0559 (9)
C9C0.7367 (6)0.2423 (2)0.1689 (3)0.0721 (13)
C10C0.6422 (7)0.2632 (2)0.2373 (3)0.0888 (17)
H10G0.66780.24910.28290.133*
H10H0.66420.29500.23860.133*
H10I0.53410.25880.23420.133*
C11C1.1210 (5)0.41647 (15)0.0355 (2)0.0553 (9)
H11C1.17790.41940.08710.066*
C12C0.9629 (5)0.43827 (15)0.0386 (2)0.0555 (9)
H12E0.89760.43250.00950.067*
H12F0.97680.47080.04320.067*
C13C0.9756 (7)0.4387 (2)0.1986 (3)0.0805 (15)
H13G0.92110.43320.24130.121*
H13H0.99370.47060.19430.121*
H13I1.07290.42300.20610.121*
C14C1.2197 (5)0.44011 (14)0.0170 (2)0.0538 (9)
C15C1.1595 (5)0.46622 (16)0.0792 (2)0.0571 (10)
H15C1.05280.46950.09130.068*
C16C1.2571 (5)0.48744 (16)0.1235 (2)0.0554 (10)
C17C1.4177 (5)0.48164 (16)0.1062 (3)0.0566 (10)
C18C1.4762 (5)0.45574 (18)0.0448 (3)0.0635 (11)
H18C1.58280.45190.03300.076*
C19C1.3774 (5)0.43526 (17)0.0000 (3)0.0632 (11)
H19C1.41850.41800.04200.076*
C20C1.0496 (5)0.5256 (2)0.2021 (3)0.0724 (13)
H20E1.01130.53800.15750.087*
H20F0.99040.49860.21810.087*
C21C1.0330 (8)0.5598 (3)0.2654 (4)0.119 (3)
H21G1.07460.54770.30870.178*
H21H1.08830.58690.24830.178*
H21I0.92530.56690.27980.178*
C22C1.6688 (6)0.4962 (3)0.1402 (4)0.0934 (19)
H22G1.71610.51040.18010.140*
H22H1.68870.46420.14010.140*
H22I1.71140.50890.09180.140*
S1D1.58527 (13)0.63238 (5)0.17125 (6)0.0674 (3)
O1D1.2430 (4)0.70438 (11)0.11523 (17)0.0645 (8)
O2D1.6356 (3)0.66231 (11)0.07166 (15)0.0571 (7)
O3D1.7832 (6)0.81306 (15)0.2139 (3)0.0966 (14)
O6D1.2557 (3)0.51776 (11)0.14024 (17)0.0584 (7)
O4D1.7108 (4)0.60859 (18)0.1271 (2)0.0919 (13)
O7D0.9671 (3)0.54095 (11)0.1048 (2)0.0616 (7)
O5D1.5955 (6)0.68090 (17)0.1733 (3)0.0992 (14)
N1D1.4371 (4)0.67134 (11)0.02876 (18)0.0480 (7)
N2D1.7159 (4)0.75019 (14)0.14381 (19)0.0574 (8)
H2D1.73700.72190.14020.069*
C1D1.6021 (5)0.76709 (15)0.0872 (2)0.0514 (9)
C2D1.5577 (6)0.81261 (17)0.0773 (3)0.0622 (10)
H2DA1.60760.83470.10920.075*
C3D1.4397 (6)0.82465 (16)0.0202 (3)0.0635 (11)
H3D1.41150.85500.01520.076*
C4D1.3614 (5)0.79360 (16)0.0300 (2)0.0587 (10)
H4D1.28250.80240.06800.070*
C5D1.4071 (4)0.74881 (14)0.0204 (2)0.0489 (8)
C6D1.3476 (5)0.70783 (15)0.0627 (2)0.0512 (9)
C7D1.5435 (4)0.68655 (14)0.0317 (2)0.0473 (8)
C8D1.5241 (4)0.73602 (14)0.0363 (2)0.0468 (8)
C9D1.7978 (6)0.77241 (18)0.2037 (3)0.0634 (11)
C10D1.9046 (6)0.7430 (2)0.2561 (3)0.0787 (14)
H10J2.00220.75820.26910.118*
H10K1.92050.71490.23100.118*
H10L1.85970.73720.30170.118*
C11D1.4239 (4)0.62291 (14)0.0500 (2)0.0510 (8)
H11D1.52110.60850.02780.061*
C12D1.4111 (5)0.61660 (16)0.1364 (2)0.0575 (9)
H12G1.32630.63490.16130.069*
H12H1.38810.58510.14900.069*
C13D1.5627 (7)0.6115 (3)0.2647 (3)0.0900 (19)
H13J1.65380.61820.28760.135*
H13K1.47430.62560.29390.135*
H13L1.54750.57930.26390.135*
C14D1.2957 (5)0.59998 (14)0.0143 (2)0.0512 (9)
C15D1.3374 (4)0.56947 (14)0.0454 (2)0.0500 (8)
H15D1.44150.56270.06010.060*
C16D1.2257 (4)0.54907 (14)0.0832 (2)0.0476 (8)
C17D1.0702 (5)0.56070 (14)0.0620 (2)0.0513 (9)
C18D1.0281 (5)0.58973 (16)0.0012 (3)0.0599 (10)
H18D0.92410.59620.01430.072*
C19D1.1412 (5)0.60930 (16)0.0370 (3)0.0585 (10)
H19D1.11230.62870.07800.070*
C20D1.4164 (5)0.50701 (17)0.1659 (3)0.0592 (10)
H20G1.46940.53330.19000.071*
H20H1.46770.49810.12290.071*
C21D1.4200 (6)0.4687 (2)0.2221 (3)0.0720 (13)
H21J1.38820.44120.19550.108*
H21K1.35080.47530.25850.108*
H21L1.52340.46520.24830.108*
C22D0.8127 (5)0.5578 (2)0.0945 (4)0.0791 (15)
H22J0.76330.55040.04410.119*
H22K0.81450.59020.10100.119*
H22L0.75610.54430.13170.119*
O10.1857 (5)0.67368 (14)0.3319 (2)0.0841 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0480 (5)0.0798 (7)0.0538 (5)0.0055 (5)0.0072 (4)0.0041 (5)
O1A0.0656 (19)0.078 (2)0.078 (2)0.0093 (17)0.0105 (16)0.0156 (18)
O2A0.0631 (17)0.0545 (16)0.0518 (14)0.0033 (14)0.0039 (13)0.0013 (12)
O3A0.135 (4)0.088 (3)0.126 (4)0.027 (3)0.015 (3)0.038 (3)
O4A0.0533 (18)0.132 (4)0.093 (2)0.017 (2)0.0215 (18)0.009 (2)
O5A0.115 (3)0.078 (3)0.105 (3)0.034 (2)0.049 (3)0.008 (2)
O6A0.0467 (15)0.074 (2)0.0714 (17)0.0051 (14)0.0087 (13)0.0175 (16)
O7A0.0488 (15)0.071 (2)0.084 (2)0.0072 (14)0.0212 (15)0.0125 (17)
N1A0.0483 (17)0.0439 (16)0.0520 (16)0.0012 (13)0.0018 (14)0.0014 (13)
N2A0.071 (2)0.064 (2)0.061 (2)0.0139 (19)0.0090 (18)0.0144 (17)
C1A0.057 (2)0.052 (2)0.064 (2)0.0066 (18)0.022 (2)0.0057 (18)
C2A0.079 (3)0.048 (2)0.102 (4)0.013 (2)0.036 (3)0.014 (2)
C3A0.074 (3)0.050 (3)0.113 (4)0.002 (2)0.037 (3)0.005 (3)
C4A0.063 (3)0.053 (2)0.096 (3)0.011 (2)0.025 (2)0.019 (2)
C5A0.0464 (19)0.048 (2)0.057 (2)0.0021 (16)0.0152 (16)0.0015 (16)
C6A0.0475 (19)0.047 (2)0.0459 (17)0.0003 (16)0.0082 (15)0.0022 (15)
C7A0.052 (2)0.047 (2)0.068 (2)0.0037 (17)0.0199 (18)0.0090 (18)
C8A0.047 (2)0.057 (2)0.062 (2)0.0093 (18)0.0072 (18)0.0119 (19)
C9A0.078 (3)0.095 (4)0.066 (3)0.031 (3)0.021 (2)0.021 (3)
C10A0.092 (4)0.123 (5)0.062 (3)0.031 (4)0.001 (3)0.003 (3)
C11A0.0493 (19)0.053 (2)0.0478 (18)0.0007 (17)0.0039 (15)0.0029 (16)
C12A0.056 (2)0.053 (2)0.059 (2)0.0012 (18)0.0079 (18)0.0054 (17)
C13A0.081 (4)0.213 (9)0.053 (3)0.008 (5)0.008 (3)0.012 (4)
C14A0.0436 (18)0.049 (2)0.0520 (18)0.0002 (16)0.0035 (15)0.0060 (16)
C15A0.046 (2)0.058 (2)0.064 (2)0.0040 (18)0.0036 (18)0.0031 (19)
C16A0.0412 (19)0.063 (3)0.076 (3)0.0038 (18)0.0066 (19)0.004 (2)
C17A0.0461 (19)0.051 (2)0.0539 (19)0.0001 (16)0.0052 (16)0.0002 (16)
C18A0.0443 (19)0.053 (2)0.066 (2)0.0020 (17)0.0114 (18)0.0022 (18)
C19A0.0396 (18)0.058 (2)0.057 (2)0.0001 (17)0.0014 (16)0.0018 (17)
C20A0.050 (2)0.068 (3)0.065 (2)0.0027 (19)0.0017 (19)0.004 (2)
C21A0.071 (3)0.100 (4)0.085 (3)0.004 (3)0.007 (3)0.026 (3)
C22A0.051 (3)0.103 (4)0.113 (4)0.017 (3)0.031 (3)0.025 (4)
S1B0.0646 (7)0.0953 (10)0.0656 (6)0.0177 (6)0.0103 (5)0.0063 (6)
O1B0.0684 (19)0.065 (2)0.0736 (19)0.0025 (16)0.0182 (16)0.0052 (16)
O2B0.0618 (17)0.0579 (17)0.0600 (15)0.0034 (14)0.0050 (13)0.0089 (13)
O4B0.147 (4)0.091 (3)0.126 (4)0.053 (3)0.057 (3)0.020 (3)
O5B0.0517 (19)0.238 (7)0.078 (2)0.006 (3)0.0021 (18)0.004 (3)
O6B0.0459 (14)0.081 (2)0.0637 (16)0.0025 (14)0.0058 (13)0.0175 (15)
O7B0.0411 (13)0.0632 (18)0.0776 (19)0.0006 (13)0.0134 (13)0.0032 (15)
N1B0.0523 (17)0.0434 (16)0.0587 (17)0.0009 (14)0.0049 (15)0.0021 (14)
N2B0.060 (2)0.058 (2)0.0605 (19)0.0094 (17)0.0051 (17)0.0019 (16)
C1B0.056 (2)0.051 (2)0.055 (2)0.0020 (18)0.0177 (18)0.0009 (17)
C2B0.064 (3)0.051 (2)0.074 (3)0.002 (2)0.018 (2)0.000 (2)
C3B0.066 (3)0.051 (2)0.071 (3)0.005 (2)0.023 (2)0.008 (2)
C4B0.056 (2)0.058 (2)0.059 (2)0.0081 (19)0.0133 (18)0.0120 (18)
C5B0.051 (2)0.048 (2)0.055 (2)0.0033 (17)0.0124 (16)0.0067 (16)
C7B0.053 (2)0.056 (2)0.058 (2)0.0021 (18)0.0025 (18)0.0056 (18)
C8X0.049 (2)0.052 (2)0.0484 (18)0.0008 (17)0.0053 (16)0.0022 (16)
C8B0.050 (2)0.047 (2)0.0505 (18)0.0024 (16)0.0100 (16)0.0015 (15)
C9B0.065 (3)0.066 (3)0.062 (2)0.012 (2)0.016 (2)0.010 (2)
C10B0.079 (3)0.090 (4)0.067 (3)0.011 (3)0.002 (2)0.003 (3)
C11B0.0466 (19)0.0438 (19)0.065 (2)0.0008 (16)0.0002 (17)0.0024 (17)
C12B0.057 (2)0.050 (2)0.070 (2)0.0036 (18)0.004 (2)0.0040 (18)
C13B0.098 (4)0.104 (5)0.067 (3)0.001 (4)0.011 (3)0.006 (3)
C14B0.049 (2)0.046 (2)0.061 (2)0.0046 (16)0.0021 (17)0.0009 (16)
C15B0.051 (2)0.056 (2)0.077 (3)0.0051 (18)0.001 (2)0.012 (2)
C16B0.0437 (19)0.058 (2)0.077 (3)0.0077 (18)0.0014 (19)0.001 (2)
C17B0.0438 (19)0.051 (2)0.060 (2)0.0004 (16)0.0071 (17)0.0101 (17)
C18B0.0457 (19)0.057 (2)0.0496 (18)0.0008 (17)0.0041 (16)0.0009 (16)
C19B0.0380 (17)0.058 (2)0.056 (2)0.0014 (16)0.0016 (16)0.0003 (17)
C20B0.048 (2)0.082 (3)0.065 (2)0.004 (2)0.0064 (19)0.010 (2)
C21B0.071 (3)0.112 (5)0.070 (3)0.001 (3)0.003 (2)0.031 (3)
C22B0.042 (2)0.094 (4)0.099 (4)0.005 (2)0.012 (2)0.002 (3)
S1C0.0516 (5)0.0724 (7)0.0619 (6)0.0098 (5)0.0083 (4)0.0060 (5)
O1C0.078 (2)0.085 (2)0.082 (2)0.000 (2)0.0189 (19)0.0138 (19)
O2C0.081 (2)0.0585 (18)0.0579 (16)0.0023 (16)0.0016 (15)0.0014 (13)
O3C0.114 (3)0.070 (3)0.103 (3)0.024 (2)0.020 (2)0.006 (2)
O4C0.116 (3)0.068 (2)0.115 (3)0.037 (2)0.044 (3)0.012 (2)
O5C0.0534 (18)0.151 (4)0.084 (2)0.016 (2)0.0119 (17)0.009 (3)
O6C0.0466 (15)0.106 (3)0.0690 (18)0.0022 (17)0.0049 (14)0.0209 (18)
O7C0.0457 (15)0.083 (2)0.087 (2)0.0028 (16)0.0166 (15)0.0039 (19)
N1C0.0562 (19)0.0504 (18)0.0602 (18)0.0013 (15)0.0025 (16)0.0025 (15)
N2C0.085 (3)0.057 (2)0.065 (2)0.008 (2)0.017 (2)0.0040 (18)
C1C0.068 (3)0.053 (2)0.063 (2)0.002 (2)0.024 (2)0.0005 (19)
C2C0.081 (3)0.055 (3)0.081 (3)0.000 (2)0.030 (3)0.004 (2)
C3C0.080 (3)0.056 (3)0.096 (3)0.009 (2)0.035 (3)0.013 (3)
C4C0.065 (3)0.064 (3)0.081 (3)0.009 (2)0.023 (2)0.020 (2)
C5C0.057 (2)0.057 (2)0.069 (2)0.0060 (19)0.020 (2)0.008 (2)
C6C0.052 (2)0.068 (3)0.068 (2)0.005 (2)0.005 (2)0.012 (2)
C7C0.057 (2)0.057 (2)0.052 (2)0.0002 (19)0.0085 (17)0.0007 (17)
C8C0.060 (2)0.050 (2)0.060 (2)0.0024 (19)0.0194 (19)0.0023 (18)
C9C0.082 (3)0.071 (3)0.068 (3)0.011 (3)0.029 (2)0.014 (2)
C10C0.093 (4)0.099 (4)0.075 (3)0.014 (3)0.014 (3)0.016 (3)
C11C0.053 (2)0.055 (2)0.057 (2)0.0005 (18)0.0026 (17)0.0030 (17)
C12C0.053 (2)0.057 (2)0.055 (2)0.0003 (18)0.0036 (17)0.0053 (17)
C13C0.084 (3)0.099 (4)0.058 (2)0.016 (3)0.006 (2)0.007 (3)
C14C0.050 (2)0.050 (2)0.060 (2)0.0024 (17)0.0053 (18)0.0065 (17)
C15C0.044 (2)0.067 (3)0.059 (2)0.0033 (18)0.0013 (17)0.0032 (19)
C16C0.046 (2)0.063 (3)0.057 (2)0.0012 (18)0.0058 (17)0.0010 (18)
C17C0.0428 (19)0.062 (3)0.065 (2)0.0018 (18)0.0084 (18)0.011 (2)
C18C0.041 (2)0.071 (3)0.078 (3)0.0039 (19)0.0060 (19)0.006 (2)
C19C0.054 (2)0.062 (3)0.071 (3)0.007 (2)0.003 (2)0.000 (2)
C20C0.048 (2)0.100 (4)0.066 (3)0.006 (2)0.004 (2)0.005 (3)
C21C0.073 (4)0.186 (9)0.089 (4)0.010 (4)0.016 (3)0.057 (5)
C22C0.047 (2)0.109 (5)0.127 (5)0.001 (3)0.020 (3)0.012 (4)
S1D0.0565 (6)0.0944 (9)0.0502 (5)0.0020 (6)0.0038 (4)0.0019 (5)
O1D0.0616 (17)0.0675 (19)0.0590 (16)0.0061 (15)0.0114 (14)0.0036 (14)
O2D0.0601 (16)0.0565 (16)0.0513 (14)0.0058 (14)0.0047 (12)0.0008 (13)
O3D0.116 (3)0.072 (2)0.091 (3)0.008 (2)0.023 (2)0.018 (2)
O6D0.0445 (14)0.0655 (18)0.0652 (16)0.0059 (13)0.0077 (12)0.0143 (14)
O4D0.0522 (18)0.158 (4)0.0615 (18)0.013 (2)0.0038 (15)0.007 (2)
O7D0.0419 (14)0.0578 (17)0.087 (2)0.0018 (12)0.0141 (14)0.0033 (15)
O5D0.112 (3)0.093 (3)0.095 (3)0.032 (3)0.025 (3)0.001 (2)
N1D0.0502 (17)0.0462 (17)0.0458 (15)0.0033 (13)0.0003 (13)0.0002 (12)
N2D0.0574 (19)0.059 (2)0.0544 (17)0.0012 (16)0.0028 (15)0.0085 (16)
C1D0.050 (2)0.053 (2)0.0519 (19)0.0029 (17)0.0105 (17)0.0002 (16)
C2D0.068 (3)0.054 (2)0.067 (2)0.003 (2)0.014 (2)0.0041 (19)
C3D0.070 (3)0.048 (2)0.074 (3)0.003 (2)0.015 (2)0.003 (2)
C4D0.062 (2)0.058 (2)0.057 (2)0.005 (2)0.0108 (19)0.0087 (19)
C5D0.0497 (19)0.050 (2)0.0481 (17)0.0034 (17)0.0124 (15)0.0070 (16)
C6D0.0479 (19)0.061 (2)0.0449 (17)0.0049 (18)0.0054 (16)0.0057 (16)
C7D0.0462 (19)0.054 (2)0.0411 (17)0.0026 (16)0.0040 (15)0.0003 (15)
C8D0.0480 (19)0.050 (2)0.0431 (16)0.0009 (16)0.0091 (15)0.0019 (15)
C9D0.062 (3)0.069 (3)0.058 (2)0.009 (2)0.0045 (19)0.009 (2)
C10D0.073 (3)0.092 (4)0.067 (3)0.005 (3)0.007 (2)0.005 (3)
C11D0.0463 (19)0.051 (2)0.0535 (19)0.0021 (16)0.0009 (16)0.0020 (16)
C12D0.055 (2)0.061 (2)0.054 (2)0.0005 (19)0.0006 (17)0.0063 (18)
C13D0.082 (3)0.134 (6)0.054 (2)0.028 (4)0.006 (2)0.000 (3)
C14D0.048 (2)0.048 (2)0.057 (2)0.0007 (16)0.0029 (17)0.0011 (16)
C15D0.0424 (18)0.050 (2)0.057 (2)0.0006 (16)0.0047 (16)0.0024 (16)
C16D0.0431 (18)0.046 (2)0.0526 (19)0.0019 (15)0.0033 (15)0.0003 (15)
C17D0.0441 (19)0.046 (2)0.064 (2)0.0018 (16)0.0066 (17)0.0045 (17)
C18D0.043 (2)0.056 (2)0.077 (3)0.0039 (18)0.0038 (19)0.004 (2)
C19D0.051 (2)0.056 (2)0.065 (2)0.0027 (18)0.0018 (19)0.0057 (19)
C20D0.044 (2)0.069 (3)0.061 (2)0.0037 (19)0.0035 (17)0.003 (2)
C21D0.067 (3)0.084 (3)0.062 (2)0.008 (3)0.001 (2)0.013 (2)
C22D0.045 (2)0.082 (4)0.112 (4)0.009 (2)0.019 (3)0.004 (3)
O10.097 (3)0.066 (2)0.087 (2)0.023 (2)0.005 (2)0.0089 (18)
Geometric parameters (Å, º) top
S1A—O4A1.421 (4)S1C—O4C1.434 (4)
S1A—O5A1.425 (5)S1C—O5C1.427 (4)
S1A—C12A1.774 (4)S1C—C12C1.785 (4)
S1A—C13A1.751 (5)S1C—C13C1.756 (5)
O1A—C8A1.209 (5)O1C—C6C1.216 (6)
O2A—C6A1.215 (5)O2C—C7C1.232 (5)
O3A—C9A1.204 (8)O3C—C9C1.217 (7)
O6A—C17A1.363 (5)O6C—C16C1.361 (6)
O6A—C20A1.422 (5)O6C—C20C1.430 (6)
O7A—C18A1.368 (6)O7C—C17C1.367 (6)
O7A—C22A1.424 (6)O7C—C22C1.435 (6)
N1A—C6A1.389 (5)N1C—C6C1.395 (6)
N1A—C8A1.398 (5)N1C—C7C1.388 (5)
N1A—C11A1.463 (5)N1C—C11C1.467 (6)
N2A—C1A1.382 (6)N2C—C1C1.395 (6)
N2A—C9A1.379 (6)N2C—C9C1.373 (7)
C1A—C2A1.418 (7)C1C—C2C1.398 (7)
C1A—C5A1.395 (6)C1C—C8C1.387 (6)
C2A—C3A1.382 (8)C2C—C3C1.377 (8)
C3A—C4A1.379 (8)C3C—C4C1.388 (8)
C4A—C7A1.380 (6)C4C—C5C1.383 (7)
C5A—C6A1.479 (6)C5C—C6C1.480 (7)
C5A—C7A1.378 (6)C5C—C8C1.390 (6)
C7A—C8A1.481 (7)C7C—C8C1.469 (6)
C9A—C10A1.492 (9)C9C—C10C1.498 (9)
C11A—C12A1.528 (6)C11C—C12C1.528 (6)
C11A—C14A1.522 (6)C11C—C14C1.518 (6)
C14A—C15A1.380 (6)C14C—C15C1.385 (6)
C14A—C19A1.395 (6)C14C—C19C1.374 (6)
C15A—C16A1.383 (7)C15C—C16C1.382 (6)
C16A—C18A1.381 (6)C16C—C17C1.401 (6)
C17A—C18A1.397 (6)C17C—C18C1.367 (7)
C17A—C19A1.391 (6)C18C—C19C1.385 (7)
C20A—C21A1.507 (7)C20C—C21C1.499 (8)
S1B—O4B1.434 (6)S1D—O4D1.435 (4)
S1B—O5B1.432 (5)S1D—O5D1.435 (5)
S1B—C12B1.771 (5)S1D—C12D1.776 (5)
S1B—C13B1.756 (6)S1D—C13D1.747 (5)
O1B—C7B1.207 (5)O1D—C6D1.212 (5)
O2B—C8X1.227 (5)O2D—C7D1.224 (5)
O6B—C18B1.359 (5)O3D—C9D1.222 (7)
O6B—C20B1.446 (5)O6D—C16D1.366 (5)
O7B—C17B1.379 (5)O6D—C20D1.446 (5)
O7B—C22B1.424 (5)O7D—C17D1.381 (5)
N1B—C7B1.408 (5)O7D—C22D1.422 (5)
N1B—C8X1.391 (5)N1D—C6D1.413 (5)
N1B—C11B1.469 (5)N1D—C7D1.389 (5)
N2B—C1B1.402 (6)N1D—C11D1.477 (5)
N2B—C9B1.368 (6)N2D—C1D1.400 (5)
C1B—C2B1.404 (6)N2D—C9D1.360 (5)
C1B—C8B1.379 (6)C1D—C2D1.401 (7)
C2B—C3B1.380 (7)C1D—C8D1.393 (6)
C3B—C4B1.395 (7)C2D—C3D1.384 (7)
C4B—C5B1.372 (6)C3D—C4D1.386 (7)
C5B—C7B1.482 (6)C4D—C5D1.383 (6)
C5B—C8B1.385 (6)C5D—C6D1.478 (6)
C8X—C8B1.474 (6)C5D—C8D1.379 (5)
C9B—C10B1.494 (7)C7D—C8D1.472 (6)
C9B—O11.215 (6)C9D—C10D1.495 (7)
C11B—C12B1.521 (6)C11D—C12D1.528 (5)
C11B—C14B1.522 (6)C11D—C14D1.515 (6)
C14B—C15B1.382 (6)C14D—C15D1.395 (6)
C14B—C19B1.389 (6)C14D—C19D1.379 (6)
C15B—C16B1.393 (7)C15D—C16D1.391 (6)
C16B—C17B1.368 (6)C16D—C17D1.398 (5)
C17B—C18B1.394 (6)C17D—C18D1.383 (6)
C18B—C19B1.394 (6)C18D—C19D1.394 (7)
C20B—C21B1.492 (7)C20D—C21D1.502 (7)
O4A—S1A—O5A118.3 (3)O4C—S1C—C12C108.9 (2)
O4A—S1A—C12A106.1 (2)O4C—S1C—C13C109.2 (3)
O4A—S1A—C13A109.0 (3)O5C—S1C—O4C119.1 (3)
O5A—S1A—C12A108.8 (2)O5C—S1C—C12C106.6 (2)
O5A—S1A—C13A108.9 (4)O5C—S1C—C13C106.9 (3)
C13A—S1A—C12A105.0 (3)C13C—S1C—C12C105.3 (2)
C17A—O6A—C20A119.2 (3)C16C—O6C—C20C118.8 (4)
C18A—O7A—C22A117.3 (4)C17C—O7C—C22C116.7 (4)
C6A—N1A—C8A111.2 (3)C6C—N1C—C11C121.7 (4)
C6A—N1A—C11A127.1 (3)C7C—N1C—C6C111.0 (4)
C8A—N1A—C11A121.7 (3)C7C—N1C—C11C126.9 (4)
C9A—N2A—C1A129.8 (5)C9C—N2C—C1C128.5 (5)
N2A—C1A—C2A125.8 (4)N2C—C1C—C2C125.3 (5)
N2A—C1A—C5A118.6 (4)C8C—C1C—N2C118.4 (4)
C5A—C1A—C2A115.7 (5)C8C—C1C—C2C116.3 (5)
C3A—C2A—C1A120.4 (5)C3C—C2C—C1C121.4 (5)
C4A—C3A—C2A123.2 (5)C2C—C3C—C4C122.4 (5)
C3A—C4A—C7A116.2 (5)C5C—C4C—C3C116.3 (5)
C1A—C5A—C6A129.2 (4)C4C—C5C—C6C130.5 (4)
C7A—C5A—C1A122.3 (4)C4C—C5C—C8C121.8 (5)
C7A—C5A—C6A108.5 (4)C8C—C5C—C6C107.7 (4)
O2A—C6A—N1A125.7 (4)O1C—C6C—N1C124.1 (5)
O2A—C6A—C5A128.1 (4)O1C—C6C—C5C129.5 (4)
N1A—C6A—C5A106.1 (3)N1C—C6C—C5C106.4 (4)
C4A—C7A—C8A130.0 (4)O2C—C7C—N1C124.8 (4)
C5A—C7A—C4A122.1 (5)O2C—C7C—C8C128.2 (4)
C5A—C7A—C8A107.8 (4)N1C—C7C—C8C107.0 (4)
O1A—C8A—N1A124.2 (4)C1C—C8C—C5C121.8 (4)
O1A—C8A—C7A129.5 (4)C1C—C8C—C7C130.2 (4)
N1A—C8A—C7A106.3 (3)C5C—C8C—C7C107.9 (4)
O3A—C9A—N2A121.8 (6)O3C—C9C—N2C122.6 (6)
O3A—C9A—C10A123.3 (5)O3C—C9C—C10C122.5 (5)
N2A—C9A—C10A114.9 (5)N2C—C9C—C10C114.9 (5)
N1A—C11A—C12A111.9 (3)N1C—C11C—C12C111.5 (3)
N1A—C11A—C14A110.6 (3)N1C—C11C—C14C112.4 (4)
C14A—C11A—C12A114.7 (3)C14C—C11C—C12C114.7 (4)
C11A—C12A—S1A116.0 (3)C11C—C12C—S1C115.2 (3)
C15A—C14A—C11A117.8 (4)C15C—C14C—C11C123.8 (4)
C15A—C14A—C19A119.2 (4)C19C—C14C—C11C116.9 (4)
C19A—C14A—C11A123.0 (3)C19C—C14C—C15C119.3 (4)
C14A—C15A—C16A120.7 (4)C16C—C15C—C14C120.4 (4)
C18A—C16A—C15A120.4 (4)O6C—C16C—C15C125.2 (4)
O6A—C17A—C18A115.7 (4)O6C—C16C—C17C115.1 (4)
O6A—C17A—C19A124.9 (4)C15C—C16C—C17C119.7 (4)
C19A—C17A—C18A119.4 (4)O7C—C17C—C16C115.4 (4)
O7A—C18A—C16A124.2 (4)C18C—C17C—O7C125.0 (4)
O7A—C18A—C17A116.1 (4)C18C—C17C—C16C119.6 (4)
C16A—C18A—C17A119.7 (4)C17C—C18C—C19C120.3 (4)
C17A—C19A—C14A120.5 (4)C14C—C19C—C18C120.8 (4)
O6A—C20A—C21A107.4 (4)O6C—C20C—C21C107.7 (5)
O4B—S1B—C12B109.4 (3)O4D—S1D—C12D107.9 (2)
O4B—S1B—C13B108.5 (3)O4D—S1D—C13D108.6 (3)
O5B—S1B—O4B119.5 (4)O5D—S1D—O4D117.1 (3)
O5B—S1B—C12B107.3 (3)O5D—S1D—C12D109.2 (3)
O5B—S1B—C13B107.0 (3)O5D—S1D—C13D109.0 (3)
C13B—S1B—C12B103.9 (3)C13D—S1D—C12D104.2 (3)
C18B—O6B—C20B118.1 (3)C16D—O6D—C20D117.3 (3)
C17B—O7B—C22B117.6 (4)C17D—O7D—C22D117.3 (4)
C7B—N1B—C11B127.3 (3)C6D—N1D—C11D127.5 (3)
C8X—N1B—C7B110.5 (3)C7D—N1D—C6D110.6 (3)
C8X—N1B—C11B121.9 (3)C7D—N1D—C11D121.9 (3)
C9B—N2B—C1B128.4 (4)C9D—N2D—C1D128.9 (4)
N2B—C1B—C2B125.6 (4)N2D—C1D—C2D125.9 (4)
C8B—C1B—N2B118.2 (4)C8D—C1D—N2D117.5 (4)
C8B—C1B—C2B116.3 (4)C8D—C1D—C2D116.6 (4)
C3B—C2B—C1B120.9 (4)C3D—C2D—C1D120.1 (4)
C2B—C3B—C4B122.4 (4)C2D—C3D—C4D123.1 (5)
C5B—C4B—C3B116.3 (4)C5D—C4D—C3D116.4 (4)
C4B—C5B—C7B129.6 (4)C4D—C5D—C6D130.1 (4)
C4B—C5B—C8B121.8 (4)C8D—C5D—C4D121.4 (4)
C8B—C5B—C7B108.5 (3)C8D—C5D—C6D108.5 (3)
O1B—C7B—N1B125.7 (4)O1D—C6D—N1D125.0 (4)
O1B—C7B—C5B128.4 (4)O1D—C6D—C5D129.1 (4)
N1B—C7B—C5B106.0 (3)N1D—C6D—C5D105.9 (3)
O2B—C8X—N1B124.6 (4)O2D—C7D—N1D124.7 (4)
O2B—C8X—C8B127.9 (4)O2D—C7D—C8D128.2 (4)
N1B—C8X—C8B107.5 (3)N1D—C7D—C8D107.0 (3)
C1B—C8B—C5B122.3 (4)C1D—C8D—C7D129.6 (4)
C1B—C8B—C8X130.2 (4)C5D—C8D—C1D122.3 (4)
C5B—C8B—C8X107.5 (3)C5D—C8D—C7D108.1 (3)
N2B—C9B—C10B114.1 (5)O3D—C9D—N2D122.3 (5)
O1—C9B—N2B122.6 (5)O3D—C9D—C10D123.1 (4)
O1—C9B—C10B123.3 (5)N2D—C9D—C10D114.7 (5)
N1B—C11B—C12B112.0 (3)N1D—C11D—C12D111.3 (3)
N1B—C11B—C14B112.3 (3)N1D—C11D—C14D111.2 (3)
C12B—C11B—C14B111.7 (3)C14D—C11D—C12D114.0 (3)
C11B—C12B—S1B112.8 (3)C11D—C12D—S1D111.5 (3)
C15B—C14B—C11B121.4 (4)C15D—C14D—C11D118.2 (3)
C15B—C14B—C19B119.1 (4)C19D—C14D—C11D122.4 (4)
C19B—C14B—C11B119.5 (3)C19D—C14D—C15D119.4 (4)
C14B—C15B—C16B119.8 (4)C16D—C15D—C14D121.0 (4)
C17B—C16B—C15B121.1 (4)O6D—C16D—C15D124.9 (3)
O7B—C17B—C18B115.4 (4)O6D—C16D—C17D116.3 (4)
C16B—C17B—O7B124.6 (4)C15D—C16D—C17D118.8 (4)
C16B—C17B—C18B119.9 (4)O7D—C17D—C16D115.5 (4)
O6B—C18B—C17B116.2 (4)O7D—C17D—C18D124.3 (4)
O6B—C18B—C19B125.1 (4)C18D—C17D—C16D120.2 (4)
C19B—C18B—C17B118.8 (4)C17D—C18D—C19D120.2 (4)
C14B—C19B—C18B121.2 (4)C14D—C19D—C18D120.2 (4)
O6B—C20B—C21B107.1 (4)O6D—C20D—C21D107.7 (4)
(cocr1l) top
Crystal data top
C22H24N2O7S·0.5(C6H6O2)·0.5(H2O)Dx = 1.421 Mg m3
Mr = 524.55Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P41212Cell parameters from 29116 reflections
a = 12.89179 (7) Åθ = 3.4–74.6°
c = 29.5087 (3) ŵ = 1.66 mm1
V = 4904.29 (7) Å3T = 100 K
Z = 80.48 × 0.30 × 0.16 mm
F(000) = 2208
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
5001 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source4965 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.048
Detector resolution: 4.1685 pixels mm-1θmax = 74.8°, θmin = 3.7°
ω scansh = 1515
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1615
Tmin = 0.250, Tmax = 1.000l = 3635
38451 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0752P)2 + 4.1347P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.047(Δ/σ)max = 0.001
wR(F2) = 0.132Δρmax = 0.90 e Å3
S = 1.08Δρmin = 0.63 e Å3
5001 reflectionsExtinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
360 parametersExtinction coefficient: 0.00080 (16)
96 restraintsAbsolute structure: Flack x determined using 1998 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.001 (6)
Hydrogen site location: mixed
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)
N10.4669 (2)0.6556 (2)0.35330 (9)0.0197 (5)
C10.2922 (3)0.6355 (3)0.45136 (11)0.0211 (7)
C20.2101 (3)0.5648 (3)0.45584 (12)0.0257 (7)
H20.17050.56460.48220.031*
C30.1872 (3)0.4948 (3)0.42127 (13)0.0295 (8)
H30.13190.44930.42520.035*
C40.2440 (3)0.4903 (3)0.38093 (12)0.0266 (7)
H40.22870.44280.35820.032*
C50.3240 (3)0.5606 (3)0.37703 (11)0.0223 (7)
C60.4005 (3)0.5761 (3)0.33970 (11)0.0217 (7)
C70.4378 (3)0.6939 (3)0.39592 (11)0.0213 (6)
C80.3477 (3)0.6319 (3)0.41069 (11)0.0213 (7)
O10.4068 (2)0.53014 (19)0.30370 (8)0.0253 (5)
O20.4814 (2)0.76488 (19)0.41554 (8)0.0247 (5)
C90.2822 (3)0.7241 (3)0.52649 (11)0.0236 (7)
C100.3436 (3)0.7970 (3)0.55515 (11)0.0283 (8)
H10A0.40420.76230.56640.043*
H10B0.30190.81990.58020.043*
H10C0.36400.85590.53730.043*
N20.3239 (2)0.7068 (2)0.48419 (9)0.0228 (6)
H2A0.37620.74490.47710.027*
O30.2019 (2)0.6829 (2)0.53957 (8)0.0286 (6)
C110.5484 (3)0.7026 (3)0.32499 (11)0.0219 (7)
H110.57490.76300.34150.026*
C120.5038 (3)0.7428 (3)0.28002 (11)0.0230 (7)
H12A0.47550.68460.26320.028*
H12B0.55970.77210.26220.028*
S10.40570 (7)0.83756 (7)0.28669 (3)0.0236 (2)
O40.4469 (2)0.9251 (2)0.31135 (9)0.0309 (6)
O50.3138 (2)0.7883 (2)0.30451 (9)0.0296 (6)
C130.3810 (3)0.8753 (3)0.23037 (13)0.0348 (9)
H13A0.35790.81630.21330.052*
H13B0.44340.90220.21710.052*
H13C0.32830.92780.23000.052*
C140.6395 (3)0.6302 (3)0.31731 (12)0.0225 (7)
C150.6528 (3)0.5752 (3)0.27652 (11)0.0233 (7)
H150.60450.58270.25330.028*
C160.7373 (3)0.5099 (3)0.27058 (11)0.0232 (7)
C170.8110 (3)0.4989 (3)0.30517 (12)0.0259 (7)
C180.7980 (3)0.5536 (3)0.34559 (12)0.0273 (7)
H180.84640.54670.36880.033*
C190.7124 (3)0.6185 (3)0.35123 (12)0.0251 (7)
H190.70430.65450.37830.030*
O60.7558 (2)0.4530 (2)0.23185 (9)0.0290 (6)
C200.6806 (3)0.4618 (3)0.19604 (12)0.0285 (8)
H20A0.67750.53280.18520.034*
H20B0.61240.44230.20700.034*
C210.7137 (4)0.3900 (4)0.15807 (15)0.0436 (10)
H21A0.66390.39340.13390.065*
H21B0.71770.32020.16930.065*
H21C0.78050.41100.14700.065*
O70.8923 (2)0.4340 (2)0.29598 (9)0.0338 (6)
C220.9610 (3)0.4118 (5)0.33264 (15)0.0474 (12)
H22A1.01490.36620.32240.071*
H22B0.92310.37920.35670.071*
H22C0.99120.47520.34350.071*
C510.5385 (4)0.5008 (4)0.46254 (14)0.0354 (18)0.5
C520.4609 (5)0.4479 (4)0.48561 (18)0.0262 (16)0.5
H520.42390.39550.47110.031*0.5
C530.4384 (5)0.4731 (5)0.53034 (18)0.049 (2)0.5
C540.4936 (5)0.5514 (5)0.55199 (15)0.0381 (19)0.5
H540.47850.56830.58190.046*0.5
C550.5712 (6)0.6044 (6)0.5289 (2)0.051 (3)0.5
H550.60820.65670.54340.061*0.5
C560.5937 (5)0.5791 (6)0.4842 (2)0.0323 (17)0.5
H560.64570.61450.46880.039*0.5
O510.5543 (6)0.4722 (7)0.4189 (3)0.063 (2)0.5
H510.61520.48200.41210.094*0.5
O530.3633 (6)0.4238 (7)0.5488 (3)0.069 (2)0.5
H530.34150.37980.53110.083*0.5
O1W0.2757 (4)0.2757 (4)0.50000.0712 (16)
H1WA0.21170.28320.49390.085*0.5
H1WB0.28310.21180.50620.085*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0220 (13)0.0205 (13)0.0166 (12)0.0002 (11)0.0002 (10)0.0012 (10)
C10.0218 (16)0.0215 (16)0.0200 (15)0.0034 (12)0.0016 (12)0.0017 (12)
C20.0255 (17)0.0250 (17)0.0267 (16)0.0010 (13)0.0023 (13)0.0005 (13)
C30.0264 (18)0.0273 (18)0.0348 (18)0.0054 (14)0.0017 (15)0.0039 (15)
C40.0283 (18)0.0254 (17)0.0262 (16)0.0018 (14)0.0004 (14)0.0041 (14)
C50.0239 (17)0.0210 (15)0.0221 (14)0.0020 (13)0.0017 (13)0.0004 (13)
C60.0248 (16)0.0188 (15)0.0215 (15)0.0003 (13)0.0041 (13)0.0001 (12)
C70.0241 (16)0.0216 (15)0.0181 (14)0.0026 (12)0.0022 (12)0.0009 (12)
C80.0219 (16)0.0226 (16)0.0194 (15)0.0030 (12)0.0026 (13)0.0011 (12)
O10.0317 (13)0.0235 (12)0.0207 (11)0.0004 (10)0.0011 (10)0.0050 (10)
O20.0255 (12)0.0280 (12)0.0205 (11)0.0051 (10)0.0008 (9)0.0051 (10)
C90.0268 (17)0.0263 (17)0.0178 (14)0.0030 (13)0.0011 (13)0.0010 (13)
C100.0308 (18)0.0335 (19)0.0208 (15)0.0004 (15)0.0017 (14)0.0051 (14)
N20.0220 (14)0.0263 (15)0.0199 (12)0.0032 (11)0.0020 (11)0.0028 (11)
O30.0287 (13)0.0344 (14)0.0226 (11)0.0035 (11)0.0046 (10)0.0005 (10)
C110.0231 (16)0.0217 (16)0.0208 (14)0.0026 (13)0.0002 (13)0.0006 (12)
C120.0278 (17)0.0228 (16)0.0185 (14)0.0015 (12)0.0012 (13)0.0014 (12)
S10.0245 (4)0.0246 (4)0.0216 (4)0.0041 (3)0.0012 (3)0.0020 (3)
O40.0345 (14)0.0254 (13)0.0327 (13)0.0034 (11)0.0012 (11)0.0047 (11)
O50.0232 (13)0.0359 (14)0.0297 (12)0.0021 (11)0.0029 (10)0.0040 (11)
C130.036 (2)0.039 (2)0.0299 (19)0.0064 (16)0.0005 (16)0.0104 (16)
C140.0237 (17)0.0233 (16)0.0205 (15)0.0023 (13)0.0010 (12)0.0012 (12)
C150.0229 (16)0.0258 (17)0.0211 (15)0.0010 (13)0.0042 (13)0.0013 (13)
C160.0255 (17)0.0218 (16)0.0225 (15)0.0007 (13)0.0008 (13)0.0010 (13)
C170.0212 (16)0.0278 (17)0.0286 (17)0.0021 (13)0.0015 (13)0.0052 (14)
C180.0242 (17)0.0329 (19)0.0249 (16)0.0022 (14)0.0031 (14)0.0060 (14)
C190.0240 (17)0.0301 (18)0.0212 (15)0.0015 (13)0.0013 (13)0.0018 (14)
O60.0289 (13)0.0307 (13)0.0272 (12)0.0061 (11)0.0004 (10)0.0038 (10)
C200.0233 (17)0.0343 (19)0.0279 (17)0.0011 (14)0.0016 (14)0.0036 (15)
C210.041 (2)0.050 (3)0.039 (2)0.005 (2)0.0010 (19)0.017 (2)
O70.0273 (14)0.0423 (16)0.0318 (13)0.0133 (11)0.0016 (11)0.0081 (12)
C220.030 (2)0.077 (3)0.035 (2)0.024 (2)0.0043 (17)0.023 (2)
C510.033 (3)0.033 (3)0.040 (3)0.001 (2)0.002 (2)0.003 (2)
C520.022 (2)0.024 (2)0.032 (3)0.0000 (19)0.001 (2)0.009 (2)
C530.050 (3)0.049 (3)0.050 (3)0.000 (2)0.001 (2)0.001 (2)
C540.042 (3)0.041 (3)0.031 (3)0.001 (2)0.001 (2)0.001 (2)
C550.051 (3)0.050 (3)0.051 (3)0.001 (2)0.002 (2)0.001 (2)
C560.028 (2)0.031 (3)0.038 (3)0.001 (2)0.000 (2)0.003 (2)
O510.054 (4)0.057 (4)0.077 (4)0.000 (3)0.001 (4)0.002 (4)
O530.057 (4)0.066 (4)0.084 (5)0.006 (3)0.001 (4)0.014 (4)
O1W0.066 (2)0.066 (2)0.082 (4)0.001 (3)0.008 (2)0.008 (2)
Geometric parameters (Å, º) top
N1—C61.395 (4)S1—O51.444 (3)
N1—C71.402 (4)S1—C131.760 (4)
N1—C111.473 (4)C14—C151.407 (5)
C1—C21.404 (5)C14—C191.381 (5)
C1—C81.398 (5)C15—C161.388 (5)
C1—N21.397 (4)C16—C171.402 (5)
C2—C31.393 (5)C16—O61.379 (4)
C3—C41.399 (5)C17—C181.396 (5)
C4—C51.378 (5)C17—O71.367 (4)
C5—C61.491 (5)C18—C191.395 (5)
C5—C81.387 (5)O6—C201.438 (4)
C6—O11.219 (4)C20—C211.514 (5)
C7—C81.476 (5)O7—C221.427 (5)
C7—O21.220 (4)C51—C521.3900
C9—C101.492 (5)C51—C561.3900
C9—N21.377 (4)C51—O511.356 (8)
C9—O31.226 (5)C52—C531.3900
C11—C121.536 (4)C53—C541.3900
C11—C141.518 (5)C53—O531.280 (7)
C12—S11.770 (4)C54—C551.3900
S1—O41.444 (3)C55—C561.3900
C6—N1—C7110.6 (3)O4—S1—O5117.53 (16)
C6—N1—C11125.3 (3)O4—S1—C13109.05 (19)
C7—N1—C11123.7 (3)O5—S1—C12108.87 (16)
C8—C1—C2116.5 (3)O5—S1—C13108.47 (19)
N2—C1—C2125.6 (3)C13—S1—C12102.40 (17)
N2—C1—C8117.9 (3)C15—C14—C11122.1 (3)
C3—C2—C1120.7 (3)C19—C14—C11119.1 (3)
C2—C3—C4122.7 (3)C19—C14—C15118.8 (3)
C5—C4—C3115.8 (3)C16—C15—C14120.6 (3)
C4—C5—C6130.1 (3)C15—C16—C17120.1 (3)
C4—C5—C8122.7 (3)O6—C16—C15124.2 (3)
C8—C5—C6107.1 (3)O6—C16—C17115.6 (3)
N1—C6—C5107.0 (3)C18—C17—C16119.3 (3)
O1—C6—N1124.5 (3)O7—C17—C16115.9 (3)
O1—C6—C5128.5 (3)O7—C17—C18124.8 (3)
N1—C7—C8106.6 (3)C19—C18—C17120.0 (3)
O2—C7—N1124.5 (3)C14—C19—C18121.2 (3)
O2—C7—C8129.0 (3)C16—O6—C20116.8 (3)
C1—C8—C7129.7 (3)O6—C20—C21107.8 (3)
C5—C8—C1121.6 (3)C17—O7—C22116.6 (3)
C5—C8—C7108.7 (3)C52—C51—C56120.0
N2—C9—C10114.1 (3)O51—C51—C52116.1 (5)
O3—C9—C10122.8 (3)O51—C51—C56123.9 (5)
O3—C9—N2123.0 (3)C51—C52—C53120.0
C9—N2—C1128.4 (3)C54—C53—C52120.0
N1—C11—C12111.2 (3)O53—C53—C52116.4 (6)
N1—C11—C14112.6 (3)O53—C53—C54123.5 (6)
C14—C11—C12111.6 (3)C53—C54—C55120.0
C11—C12—S1113.8 (2)C56—C55—C54120.0
O4—S1—C12109.45 (17)C55—C56—C51120.0
(cocr2l) top
Crystal data top
C22H24N2O7S·0.5(C6H6N2O)Dx = 1.420 Mg m3
Mr = 521.55Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P41212Cell parameters from 32527 reflections
a = 12.81222 (8) Åθ = 3.4–75.2°
c = 29.7274 (3) ŵ = 1.65 mm1
V = 4879.84 (7) Å3T = 100 K
Z = 80.41 × 0.28 × 0.25 mm
F(000) = 2192
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
4980 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source4953 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 4.1685 pixels mm-1θmax = 75.2°, θmin = 3.8°
ω scansh = 1616
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1516
Tmin = 0.746, Tmax = 1.000l = 2636
38165 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0952P)2 + 6.1533P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.058(Δ/σ)max = 0.001
wR(F2) = 0.160Δρmax = 1.06 e Å3
S = 1.07Δρmin = 0.63 e Å3
4980 reflectionsExtinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
363 parametersExtinction coefficient: 0.0009 (2)
115 restraintsAbsolute structure: Flack x determined using 2008 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.002 (4)
Hydrogen site location: inferred from neighbouring sites
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)
N10.4639 (3)0.6556 (3)0.35308 (11)0.0217 (7)
C10.2910 (3)0.6329 (3)0.45080 (14)0.0226 (8)
C20.2070 (3)0.5623 (3)0.45511 (14)0.0266 (9)
H20.16750.56150.48140.032*
C30.1831 (3)0.4941 (3)0.42044 (15)0.0288 (9)
H30.12680.44910.42410.035*
C40.2395 (3)0.4899 (3)0.38036 (15)0.0273 (9)
H40.22290.44320.35750.033*
C50.3218 (3)0.5594 (3)0.37665 (13)0.0231 (8)
C60.3971 (3)0.5762 (3)0.33938 (13)0.0220 (8)
C70.4378 (3)0.6910 (3)0.39614 (12)0.0215 (8)
C80.3460 (3)0.6293 (3)0.41090 (13)0.0215 (8)
O10.4021 (2)0.5308 (2)0.30346 (10)0.0274 (6)
O20.4830 (2)0.7608 (2)0.41635 (10)0.0263 (6)
C90.2815 (3)0.7206 (3)0.52621 (13)0.0241 (8)
C100.3442 (4)0.7931 (4)0.55460 (14)0.0301 (9)
H10A0.40440.75710.56590.045*
H10B0.30240.81710.57930.045*
H10C0.36610.85170.53680.045*
N20.3233 (3)0.7030 (3)0.48401 (11)0.0239 (7)
H2A0.37670.74050.47720.029*
O30.2012 (2)0.6787 (2)0.53907 (10)0.0302 (7)
C110.5461 (3)0.7040 (3)0.32535 (13)0.0229 (8)
H110.57200.76510.34180.027*
C120.5014 (3)0.7429 (3)0.28044 (13)0.0249 (8)
H12A0.47260.68400.26410.030*
H12B0.55780.77170.26250.030*
S10.40293 (8)0.83929 (8)0.28677 (3)0.0239 (3)
O40.4442 (3)0.9256 (2)0.31231 (11)0.0318 (7)
O50.3085 (2)0.7906 (3)0.30279 (11)0.0313 (7)
C130.3824 (4)0.8798 (4)0.23078 (16)0.0367 (11)
H13A0.36520.82040.21260.055*
H13B0.44480.91190.21950.055*
H13C0.32610.92920.22990.055*
C140.6389 (3)0.6310 (3)0.31758 (14)0.0235 (8)
C150.6532 (3)0.5773 (3)0.27696 (13)0.0239 (8)
H150.60480.58500.25390.029*
C160.7393 (3)0.5124 (3)0.27091 (14)0.0238 (8)
C170.8121 (3)0.5021 (3)0.30596 (14)0.0248 (8)
C180.7979 (3)0.5551 (3)0.34571 (14)0.0262 (8)
H180.84630.54790.36880.031*
C190.7106 (3)0.6201 (3)0.35169 (14)0.0269 (9)
H190.70140.65560.37870.032*
O60.7579 (2)0.4561 (2)0.23242 (10)0.0283 (7)
C200.6800 (3)0.4621 (4)0.19772 (15)0.0292 (9)
H20A0.67760.53220.18540.035*
H20B0.61180.44570.21010.035*
C210.7076 (4)0.3851 (4)0.16123 (16)0.0394 (11)
H21A0.65250.38300.13940.059*
H21B0.71660.31710.17420.059*
H21C0.77130.40640.14690.059*
O70.8954 (2)0.4374 (3)0.29705 (10)0.0309 (7)
C220.9654 (4)0.4194 (5)0.33412 (16)0.0402 (12)
H22A1.01880.37120.32510.060*
H22B0.92710.39090.35900.060*
H22C0.99690.48420.34300.060*
C510.4344 (8)0.4863 (9)0.5361 (3)0.091 (3)0.5
N520.4653 (9)0.4614 (8)0.4925 (3)0.055 (3)0.5
C530.5473 (8)0.5152 (9)0.4725 (3)0.073 (3)0.5
H530.56800.49850.44340.087*0.5
C540.5984 (10)0.5938 (11)0.4960 (4)0.086 (3)0.5
H540.65330.62980.48260.103*0.5
C550.5675 (11)0.6188 (10)0.5395 (4)0.101 (4)0.5
H550.60170.67140.55530.122*0.5
C560.4855 (9)0.5650 (9)0.5596 (3)0.095 (4)0.5
H560.46480.58170.58870.114*0.5
C570.3670 (10)0.4342 (11)0.5471 (5)0.120 (5)0.5
N0AA0.3326 (13)0.3584 (11)0.5151 (5)0.113 (6)0.5
H0AA0.36250.35420.48920.135*0.5
H0AB0.28200.31700.52170.135*0.5
O1AA0.317 (2)0.424 (2)0.5829 (7)0.251 (10)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0253 (17)0.0211 (15)0.0188 (15)0.0002 (13)0.0007 (13)0.0002 (13)
C10.0234 (19)0.0205 (18)0.0240 (19)0.0028 (15)0.0036 (15)0.0001 (14)
C20.025 (2)0.027 (2)0.028 (2)0.0003 (16)0.0013 (16)0.0011 (16)
C30.028 (2)0.024 (2)0.034 (2)0.0026 (17)0.0010 (17)0.0018 (17)
C40.028 (2)0.0238 (19)0.030 (2)0.0003 (17)0.0024 (17)0.0057 (16)
C50.0258 (19)0.0201 (17)0.0233 (18)0.0027 (15)0.0034 (15)0.0007 (15)
C60.0278 (19)0.0192 (18)0.0189 (18)0.0030 (15)0.0061 (15)0.0013 (14)
C70.0247 (19)0.0212 (18)0.0185 (17)0.0025 (14)0.0013 (14)0.0012 (14)
C80.0236 (18)0.0202 (17)0.0209 (18)0.0020 (14)0.0028 (15)0.0001 (14)
O10.0355 (16)0.0249 (15)0.0217 (13)0.0010 (12)0.0020 (12)0.0036 (11)
O20.0263 (14)0.0296 (15)0.0228 (13)0.0037 (11)0.0019 (11)0.0052 (12)
C90.026 (2)0.0253 (19)0.0213 (18)0.0018 (15)0.0005 (15)0.0007 (15)
C100.034 (2)0.033 (2)0.0230 (19)0.0033 (18)0.0009 (18)0.0053 (17)
N20.0237 (17)0.0268 (17)0.0212 (16)0.0032 (13)0.0023 (13)0.0053 (13)
O30.0310 (15)0.0333 (16)0.0263 (15)0.0059 (13)0.0051 (12)0.0011 (13)
C110.0224 (18)0.0248 (19)0.0215 (18)0.0010 (15)0.0004 (15)0.0006 (15)
C120.030 (2)0.0242 (19)0.0204 (18)0.0024 (15)0.0008 (16)0.0018 (15)
S10.0250 (5)0.0234 (5)0.0232 (5)0.0043 (4)0.0017 (4)0.0008 (4)
O40.0352 (16)0.0256 (15)0.0346 (16)0.0032 (12)0.0013 (13)0.0053 (13)
O50.0253 (15)0.0341 (16)0.0345 (16)0.0009 (12)0.0068 (13)0.0013 (13)
C130.039 (3)0.039 (3)0.032 (2)0.006 (2)0.0024 (19)0.0097 (19)
C140.027 (2)0.0223 (19)0.0211 (18)0.0021 (16)0.0009 (15)0.0003 (14)
C150.0237 (19)0.0251 (19)0.0230 (19)0.0029 (15)0.0050 (15)0.0016 (15)
C160.0243 (19)0.0223 (19)0.0249 (19)0.0011 (15)0.0004 (15)0.0020 (15)
C170.0214 (19)0.0252 (19)0.028 (2)0.0007 (15)0.0022 (15)0.0020 (16)
C180.0239 (19)0.029 (2)0.0254 (19)0.0001 (16)0.0051 (16)0.0036 (16)
C190.026 (2)0.031 (2)0.0239 (19)0.0012 (16)0.0008 (16)0.0018 (16)
O60.0254 (14)0.0312 (16)0.0283 (15)0.0051 (12)0.0033 (12)0.0082 (12)
C200.0220 (19)0.036 (2)0.029 (2)0.0019 (17)0.0038 (16)0.0089 (18)
C210.034 (2)0.051 (3)0.033 (2)0.004 (2)0.0010 (19)0.016 (2)
O70.0236 (14)0.0381 (17)0.0310 (16)0.0093 (13)0.0014 (12)0.0029 (13)
C220.027 (2)0.061 (3)0.032 (2)0.015 (2)0.0008 (19)0.015 (2)
C510.092 (5)0.094 (5)0.088 (6)0.040 (5)0.000 (5)0.013 (5)
N520.059 (5)0.059 (5)0.047 (6)0.025 (3)0.003 (4)0.021 (4)
C530.071 (5)0.079 (5)0.068 (5)0.029 (5)0.004 (5)0.013 (5)
C540.081 (6)0.082 (6)0.095 (6)0.016 (5)0.015 (5)0.016 (5)
C550.097 (6)0.093 (6)0.114 (6)0.007 (5)0.001 (6)0.009 (6)
C560.089 (6)0.088 (6)0.107 (6)0.022 (5)0.008 (5)0.017 (5)
C570.109 (7)0.124 (7)0.127 (7)0.040 (6)0.001 (6)0.030 (6)
N0AA0.073 (8)0.111 (10)0.154 (13)0.043 (7)0.005 (9)0.093 (9)
O1AA0.234 (15)0.260 (15)0.260 (15)0.026 (14)0.001 (13)0.021 (14)
Geometric parameters (Å, º) top
N1—C61.391 (5)S1—C131.763 (5)
N1—C71.399 (5)C14—C151.402 (6)
N1—C111.474 (5)C14—C191.376 (6)
C1—C21.413 (6)C15—C161.393 (6)
C1—C81.381 (6)C16—C171.405 (6)
C1—N21.396 (5)C16—O61.373 (5)
C2—C31.385 (6)C17—C181.375 (6)
C3—C41.395 (6)C17—O71.377 (5)
C4—C51.383 (6)C18—C191.405 (6)
C5—C61.485 (6)O6—C201.437 (5)
C5—C81.391 (5)C20—C211.508 (6)
C6—O11.218 (5)O7—C221.439 (5)
C7—C81.483 (6)C51—N521.3900
C7—O21.223 (5)C51—C561.3900
C9—C101.490 (6)C51—C571.140 (8)
C9—N21.383 (5)N52—C531.3900
C9—O31.222 (5)C53—C541.3900
C11—C121.536 (5)C54—C551.3900
C11—C141.531 (6)C55—C561.3900
C12—S11.775 (4)C57—N0AA1.429 (12)
S1—O41.441 (3)C57—O1AA1.247 (13)
S1—O51.442 (3)
C6—N1—C7110.9 (3)O4—S1—C13109.0 (2)
C6—N1—C11125.7 (3)O5—S1—C12109.28 (19)
C7—N1—C11123.1 (3)O5—S1—C13108.3 (2)
C8—C1—C2116.5 (4)C13—S1—C12102.2 (2)
C8—C1—N2118.6 (4)C15—C14—C11122.1 (4)
N2—C1—C2125.0 (4)C19—C14—C11118.0 (4)
C3—C2—C1120.3 (4)C19—C14—C15119.9 (4)
C2—C3—C4123.0 (4)C16—C15—C14120.5 (4)
C5—C4—C3116.0 (4)C15—C16—C17119.1 (4)
C4—C5—C6130.4 (4)O6—C16—C15123.9 (4)
C4—C5—C8121.7 (4)O6—C16—C17117.0 (4)
C8—C5—C6107.9 (3)C18—C17—C16120.2 (4)
N1—C6—C5106.7 (3)C18—C17—O7124.4 (4)
O1—C6—N1125.0 (4)O7—C17—C16115.4 (4)
O1—C6—C5128.3 (4)C17—C18—C19120.5 (4)
N1—C7—C8106.7 (3)C14—C19—C18119.9 (4)
O2—C7—N1125.0 (4)C16—O6—C20116.8 (3)
O2—C7—C8128.3 (4)O6—C20—C21108.6 (4)
C1—C8—C5122.4 (4)C17—O7—C22115.6 (3)
C1—C8—C7129.9 (4)N52—C51—C56120.0
C5—C8—C7107.7 (3)C57—C51—N52110.4 (8)
N2—C9—C10114.0 (4)C57—C51—C56129.6 (8)
O3—C9—C10123.4 (4)C51—N52—C53120.0
O3—C9—N2122.5 (4)C54—C53—N52120.0
C9—N2—C1129.2 (4)C53—C54—C55120.0
N1—C11—C12110.9 (3)C56—C55—C54120.0
N1—C11—C14112.4 (3)C55—C56—C51120.0
C14—C11—C12110.9 (3)C51—C57—N0AA116.2 (12)
C11—C12—S1113.5 (3)C51—C57—O1AA133.7 (19)
O4—S1—C12109.2 (2)O1AA—C57—N0AA110.1 (15)
O4—S1—O5117.74 (19)
(cocr3lf) top
Crystal data top
C22H24N2O7S·0.5(C3H6N2O)Dx = 1.363 Mg m3
Mr = 501.52Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P41212Cell parameters from 26834 reflections
a = 12.85808 (14) Åθ = 3.7–74.9°
c = 29.5715 (4) ŵ = 1.62 mm1
V = 4889.07 (13) Å3T = 100 K
Z = 80.47 × 0.24 × 0.12 mm
F(000) = 2104
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
5005 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source4888 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.040
Detector resolution: 4.1685 pixels mm-1θmax = 75.0°, θmin = 3.8°
ω scansh = 1515
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1515
Tmin = 0.576, Tmax = 1.000l = 3636
38007 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.1179P)2 + 6.0959P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.063(Δ/σ)max = 0.001
wR(F2) = 0.179Δρmax = 1.98 e Å3
S = 1.05Δρmin = 0.96 e Å3
5005 reflectionsExtinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
335 parametersExtinction coefficient: 0.0008 (3)
66 restraintsAbsolute structure: Flack x determined using 1984 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.006 (6)
Hydrogen site location: mixed
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)
N10.4649 (3)0.6546 (3)0.35360 (11)0.0222 (7)
C10.2893 (3)0.6339 (3)0.45127 (14)0.0230 (8)
C20.2053 (3)0.5645 (3)0.45526 (15)0.0262 (9)
H20.16490.56490.48130.031*
C30.1821 (4)0.4953 (4)0.42066 (16)0.0295 (10)
H30.12610.45030.42430.035*
C40.2395 (3)0.4904 (3)0.38033 (16)0.0272 (9)
H40.22310.44400.35730.033*
C50.3223 (3)0.5594 (3)0.37698 (14)0.0232 (8)
C60.3981 (4)0.5745 (3)0.33982 (14)0.0231 (8)
C70.4375 (3)0.6911 (3)0.39637 (13)0.0217 (8)
C80.3454 (3)0.6294 (3)0.41127 (14)0.0227 (8)
O10.4038 (3)0.5296 (2)0.30362 (10)0.0269 (7)
O20.4816 (3)0.7605 (2)0.41676 (10)0.0264 (7)
C90.2797 (4)0.7222 (4)0.52644 (14)0.0260 (9)
C100.3421 (4)0.7952 (4)0.55506 (15)0.0316 (10)
H10A0.40510.76150.56450.047*
H10B0.30240.81460.58120.047*
H10C0.35890.85620.53780.047*
N20.3211 (3)0.7050 (3)0.48438 (12)0.0247 (7)
H2A0.37370.74300.47740.030*
O30.2005 (3)0.6801 (3)0.53965 (10)0.0304 (7)
C110.5465 (3)0.7015 (3)0.32538 (14)0.0229 (8)
H110.57270.76220.34190.027*
C120.5021 (3)0.7416 (3)0.28060 (14)0.0245 (8)
H12A0.47360.68330.26390.029*
H12B0.55850.77060.26280.029*
S10.40402 (8)0.83733 (8)0.28678 (3)0.0248 (3)
O40.4454 (3)0.9244 (3)0.31175 (11)0.0326 (8)
O50.3107 (3)0.7890 (3)0.30390 (11)0.0314 (7)
C130.3825 (4)0.8757 (4)0.23034 (17)0.0366 (11)
H13A0.35820.81720.21320.055*
H13B0.44640.90080.21750.055*
H13C0.33130.93000.22960.055*
C140.6389 (3)0.6295 (3)0.31770 (14)0.0234 (8)
C150.6536 (3)0.5768 (3)0.27695 (14)0.0243 (8)
H150.60550.58480.25370.029*
C160.7397 (3)0.5122 (3)0.27064 (14)0.0253 (8)
C170.8124 (3)0.5017 (4)0.30584 (16)0.0271 (9)
C180.7982 (4)0.5543 (4)0.34599 (15)0.0285 (9)
H180.84670.54760.36910.034*
C190.7103 (4)0.6182 (4)0.35208 (15)0.0268 (9)
H190.70050.65280.37940.032*
O60.7586 (2)0.4563 (3)0.23211 (11)0.0294 (7)
C200.6804 (4)0.4614 (4)0.19724 (15)0.0299 (10)
H20A0.67670.53130.18500.036*
H20B0.61280.44370.20970.036*
C210.7092 (4)0.3856 (5)0.16050 (17)0.0387 (12)
H21A0.65410.38210.13870.058*
H21B0.72000.31800.17350.058*
H21C0.77200.40830.14600.058*
O70.8960 (3)0.4387 (3)0.29662 (11)0.0319 (8)
C220.9647 (4)0.4198 (5)0.33402 (18)0.0420 (13)
H22A1.02160.37710.32420.063*
H22B0.92740.38490.35770.063*
H22C0.99100.48480.34520.063*
N510.4527 (12)0.4626 (13)0.5050 (5)0.025 (2)0.5
H510.40920.41340.49950.030*0.5
C520.4582 (16)0.5225 (17)0.5452 (4)0.174 (12)0.5
H520.41530.51540.57040.208*0.5
C530.541 (2)0.595 (2)0.5404 (7)0.228 (14)0.5
H530.56130.64390.56180.273*0.5
N540.5862 (17)0.5801 (18)0.4971 (7)0.071 (3)0.5
C550.5318 (8)0.4982 (8)0.4752 (3)0.041 (2)0.5
H550.54560.47240.44650.049*0.5
O1W0.3451 (14)0.3451 (14)0.50000.228 (8)
H1WB0.28500.35170.48810.274*0.5
H1WA0.34710.28960.51190.274*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0229 (17)0.0236 (17)0.0201 (15)0.0006 (14)0.0005 (13)0.0010 (14)
C10.023 (2)0.022 (2)0.0243 (19)0.0018 (15)0.0034 (16)0.0007 (15)
C20.026 (2)0.025 (2)0.028 (2)0.0004 (16)0.0004 (16)0.0010 (16)
C30.028 (2)0.024 (2)0.036 (2)0.0057 (18)0.0009 (18)0.0021 (18)
C40.026 (2)0.024 (2)0.031 (2)0.0010 (17)0.0034 (17)0.0037 (17)
C50.022 (2)0.0231 (19)0.0243 (18)0.0002 (16)0.0026 (16)0.0002 (16)
C60.028 (2)0.0190 (19)0.0225 (19)0.0001 (16)0.0052 (16)0.0013 (15)
C70.0218 (19)0.024 (2)0.0196 (17)0.0005 (15)0.0008 (15)0.0001 (15)
C80.023 (2)0.0219 (19)0.0235 (19)0.0016 (15)0.0018 (16)0.0012 (15)
O10.0320 (16)0.0256 (15)0.0232 (14)0.0006 (13)0.0021 (13)0.0049 (12)
O20.0278 (16)0.0284 (16)0.0231 (13)0.0018 (12)0.0009 (12)0.0045 (12)
C90.029 (2)0.028 (2)0.0214 (19)0.0019 (17)0.0002 (17)0.0001 (16)
C100.032 (2)0.037 (3)0.026 (2)0.002 (2)0.0030 (19)0.0044 (19)
N20.0237 (18)0.0291 (19)0.0215 (16)0.0044 (14)0.0023 (14)0.0034 (14)
O30.0315 (17)0.0333 (17)0.0264 (14)0.0048 (14)0.0058 (13)0.0000 (13)
C110.021 (2)0.023 (2)0.0242 (19)0.0007 (16)0.0006 (16)0.0016 (15)
C120.028 (2)0.023 (2)0.0228 (18)0.0017 (15)0.0007 (16)0.0011 (16)
S10.0257 (5)0.0254 (5)0.0233 (5)0.0038 (4)0.0010 (4)0.0012 (4)
O40.0370 (18)0.0276 (16)0.0334 (16)0.0037 (13)0.0011 (14)0.0040 (13)
O50.0240 (16)0.0375 (18)0.0327 (16)0.0021 (13)0.0046 (13)0.0012 (14)
C130.038 (3)0.039 (3)0.033 (2)0.005 (2)0.002 (2)0.007 (2)
C140.024 (2)0.0229 (19)0.0235 (19)0.0002 (16)0.0007 (16)0.0009 (15)
C150.023 (2)0.025 (2)0.0248 (19)0.0004 (16)0.0028 (16)0.0010 (16)
C160.026 (2)0.025 (2)0.0244 (19)0.0004 (16)0.0003 (16)0.0012 (16)
C170.022 (2)0.029 (2)0.030 (2)0.0020 (17)0.0000 (17)0.0025 (17)
C180.025 (2)0.032 (2)0.029 (2)0.0006 (17)0.0036 (17)0.0019 (18)
C190.027 (2)0.031 (2)0.0229 (19)0.0007 (17)0.0014 (17)0.0004 (17)
O60.0255 (16)0.0340 (17)0.0286 (15)0.0067 (13)0.0022 (12)0.0064 (13)
C200.024 (2)0.036 (2)0.029 (2)0.0006 (18)0.0038 (17)0.0044 (19)
C210.036 (3)0.046 (3)0.034 (2)0.003 (2)0.001 (2)0.012 (2)
O70.0244 (16)0.0407 (19)0.0306 (16)0.0101 (14)0.0016 (13)0.0044 (14)
C220.029 (2)0.062 (4)0.034 (2)0.016 (2)0.001 (2)0.014 (2)
N510.027 (4)0.029 (4)0.018 (5)0.007 (3)0.002 (4)0.004 (4)
C520.167 (13)0.173 (13)0.181 (13)0.006 (7)0.007 (7)0.021 (7)
C530.230 (16)0.224 (15)0.228 (15)0.002 (7)0.004 (7)0.006 (7)
N540.064 (6)0.070 (6)0.080 (5)0.007 (4)0.003 (5)0.013 (5)
C550.041 (4)0.044 (5)0.037 (4)0.009 (4)0.004 (4)0.003 (4)
O1W0.215 (9)0.215 (9)0.254 (13)0.099 (10)0.072 (7)0.072 (7)
Geometric parameters (Å, º) top
N1—C61.401 (5)S1—O41.443 (4)
N1—C71.394 (5)S1—O51.443 (3)
N1—C111.471 (5)S1—C131.762 (5)
C1—C21.407 (6)C14—C151.395 (6)
C1—C81.387 (6)C14—C191.377 (6)
C1—N21.400 (5)C15—C161.396 (6)
C2—C31.388 (6)C16—C171.406 (6)
C3—C41.404 (7)C16—O61.369 (5)
C4—C51.389 (6)C17—C181.379 (7)
C5—C61.481 (6)C17—O71.372 (5)
C5—C81.388 (6)C18—C191.408 (6)
C6—O11.219 (5)O6—C201.442 (5)
C7—C81.491 (6)C20—C211.506 (7)
C7—O21.217 (5)O7—C221.436 (6)
C9—C101.497 (6)N51—C521.4200
C9—N21.371 (5)N51—C551.4200
C9—O31.217 (6)C52—C531.4200
C11—C121.532 (6)C53—N541.4200
C11—C141.523 (6)N54—C551.4200
C12—S11.772 (4)
C6—N1—C11125.0 (3)C11—C12—S1114.2 (3)
C7—N1—C6110.9 (3)O4—S1—C12109.2 (2)
C7—N1—C11123.8 (4)O4—S1—C13109.0 (2)
C8—C1—C2116.4 (4)O5—S1—C12109.2 (2)
C8—C1—N2118.2 (4)O5—S1—O4117.5 (2)
N2—C1—C2125.4 (4)O5—S1—C13108.8 (2)
C3—C2—C1120.6 (4)C13—S1—C12102.0 (2)
C2—C3—C4122.8 (4)C15—C14—C11122.0 (4)
C5—C4—C3115.8 (4)C19—C14—C11118.3 (4)
C4—C5—C6129.9 (4)C19—C14—C15119.7 (4)
C8—C5—C4121.7 (4)C14—C15—C16120.8 (4)
C8—C5—C6108.4 (4)C15—C16—C17119.0 (4)
N1—C6—C5106.5 (3)O6—C16—C15124.4 (4)
O1—C6—N1124.5 (4)O6—C16—C17116.6 (4)
O1—C6—C5129.0 (4)C18—C17—C16120.1 (4)
N1—C7—C8106.8 (3)O7—C17—C16115.5 (4)
O2—C7—N1125.3 (4)O7—C17—C18124.4 (4)
O2—C7—C8127.9 (4)C17—C18—C19120.2 (4)
C1—C8—C5122.6 (4)C14—C19—C18120.1 (4)
C1—C8—C7130.0 (4)C16—O6—C20116.6 (3)
C5—C8—C7107.4 (4)O6—C20—C21108.4 (4)
N2—C9—C10113.9 (4)C17—O7—C22115.4 (4)
O3—C9—C10123.1 (4)C55—N51—C52108.0
O3—C9—N2123.0 (4)C53—C52—N51108.0
C9—N2—C1128.8 (4)N54—C53—C52108.0
N1—C11—C12111.3 (3)C53—N54—C55108.0
N1—C11—C14113.1 (3)N51—C55—N54108.0
C14—C11—C12111.5 (3)
(cocr4lf) top
Crystal data top
C22H24N2O7S·0.5(C6H8O3)Dx = 1.421 Mg m3
Mr = 524.55Cu Kα radiation, λ = 1.54184 Å
Tetragonal, P41212Cell parameters from 31560 reflections
a = 12.88747 (7) Åθ = 3.7–75.2°
c = 29.5246 (3) ŵ = 1.66 mm1
V = 4903.65 (7) Å3T = 100 K
Z = 80.26 × 0.16 × 0.12 mm
F(000) = 2208
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
5046 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source5005 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.027
Detector resolution: 4.1685 pixels mm-1θmax = 75.4°, θmin = 3.7°
ω scansh = 1615
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1515
Tmin = 0.603, Tmax = 1.000l = 2636
38399 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.1156P)2 + 5.1206P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.060(Δ/σ)max = 0.011
wR(F2) = 0.172Δρmax = 1.23 e Å3
S = 1.06Δρmin = 0.97 e Å3
5046 reflectionsExtinction correction: SHELXL-2014/7 (Sheldrick 2014, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
359 parametersExtinction coefficient: 0.0014 (3)
114 restraintsAbsolute structure: Flack x determined using 2039 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.003 (4)
Hydrogen site location: mixed
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)
N10.4651 (3)0.6554 (3)0.35354 (10)0.0218 (7)
C10.2906 (3)0.6352 (3)0.45141 (13)0.0219 (8)
C20.2072 (3)0.5641 (3)0.45568 (14)0.0277 (8)
H20.16740.56380.48190.033*
C30.1842 (3)0.4945 (3)0.42077 (15)0.0304 (9)
H30.12840.44940.42440.036*
C40.2415 (3)0.4900 (3)0.38079 (14)0.0276 (8)
H40.22620.44280.35790.033*
C50.3226 (3)0.5599 (3)0.37716 (13)0.0245 (8)
C60.3985 (3)0.5757 (3)0.33977 (13)0.0230 (8)
C70.4371 (3)0.6918 (3)0.39631 (12)0.0217 (7)
C80.3465 (3)0.6305 (3)0.41098 (13)0.0229 (8)
O10.4040 (2)0.5307 (2)0.30356 (10)0.0281 (6)
O20.4814 (2)0.7619 (2)0.41669 (9)0.0268 (6)
C90.2798 (3)0.7227 (3)0.52673 (13)0.0253 (8)
C100.3417 (4)0.7957 (4)0.55544 (14)0.0297 (9)
H10A0.40060.75980.56780.045*
H10B0.29920.82120.57970.045*
H10C0.36510.85280.53730.045*
N20.3218 (3)0.7058 (3)0.48444 (11)0.0241 (7)
H2A0.37420.74390.47750.029*
O30.2001 (2)0.6807 (3)0.53947 (10)0.0310 (7)
C110.5465 (3)0.7022 (3)0.32520 (13)0.0238 (8)
H110.57290.76270.34170.029*
C120.5021 (3)0.7425 (3)0.28043 (13)0.0251 (8)
H12A0.47370.68430.26360.030*
H12B0.55820.77150.26260.030*
S10.40433 (8)0.83764 (8)0.28677 (3)0.0253 (3)
O40.4448 (3)0.9240 (2)0.31234 (11)0.0341 (7)
O50.3110 (2)0.7888 (3)0.30332 (11)0.0312 (7)
C130.3832 (4)0.8776 (4)0.23061 (16)0.0385 (11)
H13A0.36200.81910.21270.058*
H13B0.44610.90600.21850.058*
H13C0.32980.92950.23000.058*
C140.6381 (3)0.6304 (3)0.31741 (14)0.0245 (8)
C150.6526 (3)0.5767 (3)0.27641 (13)0.0245 (8)
H150.60440.58430.25320.029*
C160.7377 (3)0.5126 (3)0.27010 (14)0.0255 (8)
C170.8116 (3)0.5025 (3)0.30478 (15)0.0283 (9)
C180.7973 (3)0.5550 (4)0.34527 (15)0.0299 (9)
H180.84560.54790.36850.036*
C190.7104 (3)0.6188 (3)0.35144 (14)0.0286 (9)
H190.70140.65370.37870.034*
O60.7563 (2)0.4572 (2)0.23120 (10)0.0303 (7)
C200.6791 (3)0.4631 (4)0.19619 (15)0.0315 (9)
H20A0.67470.53340.18460.038*
H20B0.61170.44390.20820.038*
C210.7095 (4)0.3899 (5)0.15889 (18)0.0459 (13)
H21A0.65730.39060.13570.069*
H21B0.71620.32100.17090.069*
H21C0.77470.41140.14620.069*
O70.8942 (3)0.4394 (3)0.29568 (11)0.0370 (8)
C220.9622 (4)0.4177 (5)0.33275 (17)0.0474 (14)
H22A1.01570.37090.32300.071*
H22B0.92350.38650.35700.071*
H22C0.99320.48110.34320.071*
C510.4508 (8)0.4438 (8)0.4947 (3)0.047 (2)0.5
C520.4253 (8)0.4741 (8)0.5385 (3)0.086 (4)0.5
H520.37190.44070.55390.103*0.5
C530.4796 (8)0.5541 (8)0.5593 (2)0.065 (3)0.5
H530.46250.57440.58860.077*0.5
C540.5595 (9)0.6039 (9)0.5363 (3)0.107 (4)0.5
C550.5850 (8)0.5737 (9)0.4925 (3)0.069 (3)0.5
H550.63840.60700.47710.083*0.5
C560.5307 (7)0.4936 (7)0.4717 (2)0.062 (3)0.5
H560.54780.47330.44240.074*0.5
O510.4033 (12)0.3598 (11)0.4762 (5)0.162 (7)0.5
H510.36030.33680.49400.242*0.5
O540.5925 (18)0.6980 (14)0.5521 (6)0.221 (10)0.5
H540.65150.70950.54280.331*0.5
O1W0.2851 (15)0.2851 (15)0.50000.248 (9)
H1WA0.22110.28320.49390.298*0.5
H1WB0.29250.21180.50620.298*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0250 (16)0.0216 (15)0.0188 (14)0.0015 (13)0.0032 (12)0.0022 (12)
C10.0240 (18)0.0206 (17)0.0211 (17)0.0020 (14)0.0033 (14)0.0012 (14)
C20.027 (2)0.027 (2)0.028 (2)0.0022 (16)0.0004 (16)0.0003 (16)
C30.031 (2)0.027 (2)0.034 (2)0.0051 (17)0.0004 (17)0.0033 (16)
C40.031 (2)0.0229 (18)0.029 (2)0.0014 (16)0.0014 (16)0.0052 (16)
C50.030 (2)0.0220 (17)0.0219 (17)0.0010 (15)0.0029 (15)0.0017 (14)
C60.0270 (18)0.0194 (17)0.0225 (18)0.0001 (15)0.0045 (15)0.0011 (14)
C70.0236 (18)0.0220 (17)0.0194 (16)0.0005 (14)0.0015 (14)0.0006 (14)
C80.0245 (18)0.0230 (18)0.0211 (18)0.0003 (14)0.0027 (15)0.0011 (14)
O10.0366 (16)0.0257 (14)0.0221 (13)0.0004 (12)0.0029 (12)0.0054 (11)
O20.0294 (14)0.0301 (15)0.0209 (13)0.0050 (11)0.0022 (11)0.0060 (11)
C90.029 (2)0.0257 (19)0.0208 (18)0.0028 (15)0.0012 (15)0.0008 (15)
C100.031 (2)0.036 (2)0.0222 (18)0.0010 (17)0.0004 (16)0.0035 (17)
N20.0254 (16)0.0278 (17)0.0191 (14)0.0045 (13)0.0024 (13)0.0021 (13)
O30.0322 (15)0.0351 (16)0.0256 (14)0.0042 (13)0.0046 (12)0.0005 (12)
C110.0236 (19)0.0264 (19)0.0215 (17)0.0029 (15)0.0000 (15)0.0012 (14)
C120.030 (2)0.0254 (18)0.0195 (17)0.0016 (15)0.0009 (15)0.0016 (15)
S10.0268 (5)0.0264 (5)0.0227 (4)0.0035 (4)0.0001 (4)0.0020 (4)
O40.0375 (17)0.0282 (15)0.0367 (16)0.0035 (13)0.0004 (13)0.0065 (13)
O50.0259 (15)0.0344 (16)0.0332 (15)0.0011 (12)0.0031 (12)0.0039 (13)
C130.041 (3)0.044 (3)0.030 (2)0.007 (2)0.0024 (19)0.0119 (19)
C140.027 (2)0.0252 (18)0.0214 (18)0.0005 (16)0.0020 (15)0.0009 (14)
C150.0247 (19)0.0272 (19)0.0216 (18)0.0005 (15)0.0023 (15)0.0010 (15)
C160.0280 (19)0.0239 (19)0.0246 (18)0.0002 (15)0.0004 (15)0.0015 (15)
C170.0229 (19)0.032 (2)0.030 (2)0.0007 (16)0.0019 (16)0.0054 (16)
C180.027 (2)0.033 (2)0.030 (2)0.0015 (16)0.0062 (17)0.0044 (17)
C190.030 (2)0.034 (2)0.0217 (18)0.0004 (17)0.0045 (16)0.0007 (16)
O60.0300 (15)0.0326 (16)0.0284 (14)0.0047 (12)0.0014 (12)0.0039 (12)
C200.0239 (19)0.038 (2)0.032 (2)0.0020 (17)0.0002 (16)0.0077 (18)
C210.039 (3)0.058 (3)0.041 (3)0.005 (2)0.000 (2)0.021 (2)
O70.0298 (16)0.0481 (19)0.0331 (16)0.0134 (14)0.0028 (13)0.0087 (14)
C220.033 (2)0.072 (4)0.037 (2)0.023 (3)0.005 (2)0.022 (3)
C510.045 (5)0.061 (6)0.034 (5)0.028 (4)0.015 (4)0.025 (4)
C520.080 (6)0.086 (7)0.093 (7)0.017 (6)0.006 (6)0.013 (6)
C530.063 (6)0.061 (6)0.070 (6)0.011 (5)0.006 (5)0.018 (5)
C540.090 (7)0.114 (7)0.117 (7)0.009 (6)0.015 (6)0.037 (7)
C550.045 (5)0.079 (6)0.084 (7)0.016 (4)0.018 (5)0.043 (6)
C560.045 (5)0.070 (6)0.070 (6)0.021 (5)0.008 (5)0.032 (5)
O510.160 (12)0.154 (11)0.170 (12)0.046 (11)0.008 (11)0.053 (10)
O540.214 (16)0.238 (17)0.210 (16)0.025 (15)0.016 (14)0.009 (14)
O1W0.246 (10)0.246 (10)0.253 (15)0.087 (13)0.037 (9)0.037 (9)
Geometric parameters (Å, º) top
N1—C61.399 (5)S1—O51.443 (3)
N1—C71.395 (5)S1—C131.757 (5)
N1—C111.472 (5)C14—C151.407 (6)
C1—C21.418 (6)C14—C191.378 (6)
C1—C81.396 (6)C15—C161.385 (6)
C1—N21.393 (5)C16—C171.405 (6)
C2—C31.398 (6)C16—O61.374 (5)
C3—C41.394 (6)C17—C181.386 (6)
C4—C51.385 (6)C17—O71.365 (5)
C5—C61.488 (6)C18—C191.402 (6)
C5—C81.386 (5)O6—C201.437 (5)
C6—O11.218 (5)C20—C211.502 (6)
C7—C81.474 (5)O7—C221.430 (6)
C7—O21.227 (5)C51—C521.3900
C9—C101.496 (6)C51—C561.3900
C9—N21.378 (5)C51—O511.359 (5)
C9—O31.221 (5)C52—C531.3900
C11—C121.531 (5)C53—C541.3900
C11—C141.518 (6)C54—C551.3900
C12—S11.769 (4)C54—O541.367 (6)
S1—O41.443 (3)C55—C561.3900
C6—N1—C11125.0 (3)O4—S1—O5117.4 (2)
C7—N1—C6110.6 (3)O4—S1—C13108.9 (2)
C7—N1—C11124.2 (3)O5—S1—C12109.11 (19)
C8—C1—C2116.1 (4)O5—S1—C13108.5 (2)
N2—C1—C2125.3 (4)C13—S1—C12102.4 (2)
N2—C1—C8118.5 (4)C15—C14—C11122.3 (4)
C3—C2—C1120.7 (4)C19—C14—C11118.8 (4)
C4—C3—C2122.6 (4)C19—C14—C15119.0 (4)
C5—C4—C3116.0 (4)C16—C15—C14120.9 (4)
C4—C5—C6129.9 (4)C15—C16—C17119.6 (4)
C4—C5—C8122.7 (4)O6—C16—C15124.1 (4)
C8—C5—C6107.4 (4)O6—C16—C17116.3 (4)
N1—C6—C5106.7 (3)C18—C17—C16119.5 (4)
O1—C6—N1124.6 (4)O7—C17—C16116.1 (4)
O1—C6—C5128.7 (4)O7—C17—C18124.3 (4)
N1—C7—C8106.9 (3)C17—C18—C19120.3 (4)
O2—C7—N1124.8 (4)C14—C19—C18120.6 (4)
O2—C7—C8128.3 (3)C16—O6—C20116.9 (3)
C1—C8—C7129.6 (4)O6—C20—C21108.2 (4)
C5—C8—C1122.0 (4)C17—O7—C22116.3 (4)
C5—C8—C7108.4 (3)C52—C51—C56120.0
N2—C9—C10113.8 (4)O51—C51—C52119.4 (4)
O3—C9—C10123.6 (4)O51—C51—C56120.3 (4)
O3—C9—N2122.6 (4)C51—C52—C53120.0
C9—N2—C1128.7 (4)C54—C53—C52120.0
N1—C11—C12111.3 (3)C55—C54—C53120.0
N1—C11—C14113.0 (3)O54—C54—C53118.3 (5)
C14—C11—C12111.5 (3)O54—C54—C55119.5 (5)
C11—C12—S1114.2 (3)C54—C55—C56120.0
O4—S1—C12109.5 (2)C55—C56—C51120.0
 

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