organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

N,N,N-Tri­ethyl­ethanaminium 5,11,17,23-tetra-tert-butyl-25-[(eth­­oxy­carbon­yl)­meth­oxy]-26,28-dihy­dr­oxy-27-oxido-2,8,14,20-tetra­thia­calix[4]arene: a mol­ecular salt

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eChemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt, and fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 14 September 2016; accepted 16 September 2016; online 23 September 2016)

In the title mol­ecular salt, C8H20N+·C44H53O6S4, the conformation of the anionic tetra­thia­calix[4]arene, which is cone-shaped, is primarily determined by intra­molecular O—H⋯O hydrogen bonds. There are also short intra­molecular C— H⋯O contacts present. The guest species do not sit within the bowl of the calixarene. One of the t-butyl groups in the anion is disordered over two sets of sites with refined occupancies of 0.706 (6) and 0.294 (6). Atoms of both cations are equally disordered over centers of symmetry. In the crystal, extensive O—H⋯O and C—H⋯O hydrogen bonds and weak O—H⋯S inter­actions link the thia­calixarene anions and tetra­ethyl­ammonium cations, forming a three-dimensional network.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Calixarenes (Gutsche, 1989[Gutsche, C. D. (1989). Calixarenes Revisited. In Monograph in Supramolecular Chemistry, edited by J. F. Stoddart. Cambridge: The Royal Society of Chemistry.]) have been used extensively as mol­ecular platforms to build up supra­molecular structures. The design of this kind of structure consists of function­alizing the upper and lower rims of the calixarenes with ligands able to bind to metal cations or other active functional groups. Their numerous applications include catalysis (Homden & Redshaw, 2008[Homden, D. M. & Redshaw, C. (2008). Chem. Rev. 108, 5086-5130.]) and metal recognition (Arora et al., 2007[Arora, V., Chawla, H. M. & Singh, S. P. (2007). ARKIVOC, (ii), 172-200.]). Since its discovery in 1997, p-tert-butyl­thia­calixarene, which is a calixarene analogue with additional features due to the presence of the bridging sulfur atoms in the skeleton structure, has attracted a great deal of research beyond that on the classical calixarenes. This includes work on a wide range of applications in supra­molecular chemistry (Iki & Miyano, 2001[Iki, N. & Miyano, S. (2001). J. Inclusion Phenom. Macrocyclic Chem. 41, 99-105.]). Based on these findings and as an extension of our work on related compounds, we report here the synthesis and crystal structure of the title thia­calixarene salt.

The calixarene unit (Fig. 1[link]) displays a cone conformation. Its bond lengths and bond angles are comparable to those in the inclusion complex 25-benzoyl­meth­oxy-5,11,17,23-tetra-tert-butyl-26,27,28-trihy­droxy-2,8,14,20-tetra­thia­calix[4]-arene–tetra­ethyl­ammonium chloride (1/1) (Akkurt et al., 2015[Akkurt, M., Jasinski, J. P., Mohamed, S. K., Omran, O. A. & Albayati, M. R. (2015). Acta Cryst. E71, o830-o831.]) and the mol­ecular salt N,N,N-triethyl-3-ethanaminium-5,11,17,23-tetra-tert-butyl-25-cyano­meth­oxy-26,28-dihy­droxy-27-oxido-2,8,14,20-tetra­thia­calix[4]arene (Omran et al., 2016[Omran, O. A., Mague, J. T., Mohamed, S. K., Akkurt, M. & Mohamed, A. F. (2016). IUCrData, 1, x160115.]). The conformation of the anionic calix[4]arene anion is primarily determined by the intra­molecular O—H⋯O hydrogen bonds and to a lesser extent by short C—H⋯O contacts (Fig. 1[link] and Table 1[link]). In the crystal, anions and cations are linked by C—H⋯O hydrogen bonds, forming a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O2 0.87 1.75 2.607 (3) 166
O3—H3A⋯O2 0.87 1.69 2.539 (3) 166
C3—H3⋯O5ii 0.95 2.57 3.347 (4) 139
C41—H41A⋯O3 0.99 2.48 3.444 (4) 165
C52—H52B⋯O4i 0.96 2.60 3.544 (16) 169
C57—H57A⋯O2iii 0.97 2.30 3.158 (7) 147
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1.
[Figure 1]
Figure 1
The anion of the title salt with labeling scheme and 50% probability ellipsoids. Intra­molecular hydrogen bonds are shown as dashed lines. Only the major occupancy component of the disordered t-butyl group is shown and, for clarity, the two fully disordered cations are omitted.

Synthesis and crystallization

A mixture of p-tert-butyl thia­calix[4]arene (TCA) (1 g, 1.38 mmol), anhydrous K2CO3 (5.0 g), tetra­ethyl­ammonium bromide (TEAB; 0.5 g) and ethyl bromo­acetate (0.15 ml, 1.38 mmol) in 50 ml benzene was heated under reflux at 373 K for 2 d. The mixture was filtered to remove any impurities and non-reacted material. The filtrate was evaporated to almost dryness. The viscous residue was treated with 50 ml methanol and left overnight. The colourless crystals that formed were filtered off and dried under vacuum (yield ca 90%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. One t-butyl group is rotationally disordered over two resolved sites with an occupancy ratio 0.706 (6):0.294 (6). The two components were refined subject to restraints that their geometries be approximately the same. Both cations are equally disordered over centers of symmetry and were refined subject to restraints that their geometries be regular.

Table 2
Experimental details

Crystal data
Chemical formula C8H20N+·C44H53O6S4
Mr 936.35
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 150
a, b, c (Å) 9.9806 (4), 15.6499 (6), 17.5330 (7)
α, β, γ (°) 87.413 (2), 83.429 (2), 81.713 (2)
V3) 2691.03 (18)
Z 2
Radiation type Cu Kα
μ (mm−1) 1.98
Crystal size (mm) 0.22 × 0.12 × 0.07
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.71, 0.87
No. of measured, independent and observed [I > 2σ(I)] reflections 46349, 10841, 9347
Rint 0.048
(sin θ/λ)max−1) 0.626
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.188, 1.11
No. of reflections 10841
No. of parameters 654
No. of restraints 153
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 2.06, −0.53
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014/7 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N,N,N-Triethylethanaminium 5,11,17,23-tetra-tert-butyl-25-[(ethoxycarbonyl)methoxy]-26,28-dihydroxy-27-oxido-2,8,14,20-tetrathiacalix[4]arene: a molecular salt top
Crystal data top
C8H20N+·C44H53O6S4Z = 2
Mr = 936.35F(000) = 1008
Triclinic, P1Dx = 1.156 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 9.9806 (4) ÅCell parameters from 9537 reflections
b = 15.6499 (6) Åθ = 2.5–74.5°
c = 17.5330 (7) ŵ = 1.98 mm1
α = 87.413 (2)°T = 150 K
β = 83.429 (2)°Column, colourless
γ = 81.713 (2)°0.22 × 0.12 × 0.07 mm
V = 2691.03 (18) Å3
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
10841 independent reflections
Radiation source: INCOATEC IµS micro-focus source9347 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.048
Detector resolution: 10.4167 pixels mm-1θmax = 74.7°, θmin = 2.9°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1919
Tmin = 0.71, Tmax = 0.87l = 2121
46349 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: mixed
wR(F2) = 0.188H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0698P)2 + 5.6956P]
where P = (Fo2 + 2Fc2)/3
10841 reflections(Δ/σ)max = 0.001
654 parametersΔρmax = 2.06 e Å3
153 restraintsΔρmin = 0.53 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.46809 (8)0.49576 (5)0.38104 (5)0.0289 (2)
S20.13554 (7)0.31004 (5)0.24231 (5)0.0275 (2)
S30.52535 (8)0.02517 (5)0.22563 (5)0.0286 (2)
S40.84948 (8)0.20761 (5)0.37261 (4)0.0258 (2)
O10.3530 (2)0.33889 (14)0.34716 (13)0.0291 (7)
O20.3563 (2)0.18145 (14)0.30363 (12)0.0273 (6)
O30.5936 (2)0.14732 (15)0.34589 (13)0.0309 (7)
O40.6659 (2)0.35546 (14)0.44602 (12)0.0261 (6)
O50.6979 (3)0.28423 (19)0.58736 (15)0.0443 (9)
O60.4813 (4)0.2546 (2)0.59910 (16)0.0620 (11)
C10.2972 (3)0.4091 (2)0.30901 (17)0.0243 (8)
C20.3371 (3)0.4894 (2)0.32156 (17)0.0249 (8)
C30.2747 (3)0.5643 (2)0.28872 (18)0.0270 (9)
C40.1715 (3)0.5645 (2)0.24076 (18)0.0279 (9)
C50.1373 (3)0.4840 (2)0.22570 (18)0.0275 (9)
C60.1982 (3)0.4072 (2)0.25863 (17)0.0240 (8)
C70.1082 (4)0.6498 (2)0.2051 (2)0.0363 (11)
C80.2193 (5)0.6896 (3)0.1552 (3)0.0538 (14)
C90.0468 (4)0.7118 (2)0.2694 (2)0.0421 (11)
C100.0038 (5)0.6369 (3)0.1564 (3)0.0588 (16)
C110.3580 (3)0.1824 (2)0.22850 (18)0.0242 (8)
C120.2732 (3)0.2460 (2)0.18884 (18)0.0252 (9)
C130.2868 (3)0.2526 (2)0.10933 (18)0.0262 (9)
C140.3810 (3)0.1971 (2)0.06355 (18)0.0256 (8)
C150.4551 (3)0.1294 (2)0.10176 (18)0.0263 (9)
C160.4433 (3)0.12080 (19)0.18184 (18)0.0246 (8)
C170.3929 (3)0.2070 (2)0.02452 (19)0.0305 (9)
C180.2708 (5)0.1757 (4)0.0540 (2)0.0567 (18)
C190.3916 (6)0.3020 (3)0.0494 (3)0.0589 (16)
C200.5233 (5)0.1563 (3)0.0624 (2)0.0569 (16)
C210.6987 (3)0.10936 (19)0.29917 (17)0.0245 (8)
C220.6868 (3)0.05206 (19)0.24193 (18)0.0253 (8)
C230.8029 (3)0.01268 (19)0.19769 (18)0.0250 (8)
C240.9336 (3)0.02840 (19)0.20733 (17)0.0235 (8)
C250.9440 (3)0.08845 (19)0.26252 (17)0.0244 (8)
C260.8306 (3)0.12798 (19)0.30730 (17)0.0245 (8)
C271.0618 (3)0.0117 (2)0.15774 (18)0.0273 (9)
C281.0304 (3)0.0785 (2)0.10379 (19)0.0317 (10)
C291.1681 (4)0.0550 (3)0.2085 (2)0.0377 (11)
C301.1207 (4)0.0601 (3)0.1081 (2)0.0406 (11)
C310.6762 (3)0.35961 (19)0.36644 (16)0.0220 (8)
C320.5989 (3)0.42567 (19)0.32802 (18)0.0246 (8)
C330.6177 (3)0.4328 (2)0.24818 (18)0.0270 (9)
C340.7089 (3)0.3731 (2)0.20490 (18)0.0260 (9)
C350.7833 (3)0.3065 (2)0.24414 (17)0.0245 (8)
C360.7663 (3)0.29866 (19)0.32440 (17)0.0226 (8)
C370.7281 (4)0.3785 (2)0.11688 (19)0.0339 (10)
C380.6134 (8)0.4411 (5)0.0832 (4)0.059 (2)0.706 (6)
C390.7155 (9)0.2896 (4)0.0858 (3)0.059 (2)0.706 (6)
C400.8640 (8)0.4062 (7)0.0899 (4)0.069 (3)0.706 (6)
C410.5647 (3)0.3054 (2)0.47958 (17)0.0288 (9)
C420.5938 (4)0.2804 (2)0.56065 (19)0.0344 (10)
C430.4916 (8)0.2275 (5)0.6789 (3)0.093 (3)
C440.3632 (9)0.1984 (6)0.7084 (4)0.127 (4)
C38A0.5941 (13)0.3871 (11)0.0869 (9)0.059 (2)0.294 (6)
C39A0.8170 (17)0.2982 (9)0.0817 (8)0.059 (2)0.294 (6)
C40A0.7998 (19)0.4590 (10)0.0951 (10)0.069 (3)0.294 (6)
N11.000000.500000.500000.0450 (14)
C450.9800 (6)0.5207 (5)0.4162 (2)0.048 (2)0.500
C460.8365 (9)0.5479 (12)0.3991 (5)0.058 (2)0.500
C470.9322 (7)0.4206 (3)0.5234 (4)0.053 (3)0.500
C481.0034 (17)0.3371 (4)0.4915 (10)0.083 (4)0.500
C491.1519 (3)0.4855 (5)0.5063 (3)0.048 (2)0.500
C501.1933 (9)0.4517 (12)0.5826 (5)0.058 (2)0.500
C510.9333 (7)0.5744 (3)0.5499 (4)0.062 (3)0.500
C520.9833 (16)0.6592 (4)0.5308 (9)0.073 (4)0.500
N20.8401 (4)0.0345 (2)0.5115 (2)0.0351 (17)0.500
C530.7118 (6)0.0254 (4)0.4961 (4)0.051 (3)0.500
C540.6053 (8)0.0420 (6)0.5630 (6)0.074 (3)0.500
C550.9329 (6)0.0409 (4)0.4366 (3)0.040 (2)0.500
C561.0600 (10)0.1045 (8)0.4360 (6)0.050 (4)0.500
C570.8002 (7)0.1210 (4)0.5410 (4)0.0491 (17)0.500
C580.7307 (10)0.1667 (5)0.4870 (6)0.074 (3)0.500
C590.9115 (8)0.0013 (5)0.5724 (4)0.055 (3)0.500
C600.9523 (19)0.0889 (7)0.5552 (9)0.076 (7)0.500
H50.070200.481300.191900.0330*
H8A0.287300.703000.187300.0810*
H8B0.179200.742800.130000.0810*
H8C0.263100.648700.116200.0810*
H1A0.342600.289900.328700.0440*
H30.302700.617800.299000.0320*
H3A0.513500.150400.330100.0460*
H10A0.042700.692900.135300.0880*
H10B0.075300.610800.188300.0880*
H10C0.034500.598600.114200.0880*
H130.229600.296900.085100.0310*
H150.515700.087700.072400.0320*
H18A0.274800.185900.109800.0850*
H18B0.186300.207300.029200.0850*
H18C0.272800.113800.042100.0850*
H19A0.468000.324200.030300.0880*
H19B0.305700.335400.028300.0880*
H19C0.400200.307200.105600.0880*
H20A0.530200.168000.118000.0860*
H9A0.118200.721600.300700.0630*
H9B0.024900.686400.301800.0630*
H9C0.007900.766900.246800.0630*
H251.031300.102400.269400.0290*
H28A1.114800.103000.073500.0470*
H28B0.965700.050600.069200.0470*
H28C0.990700.124700.134000.0470*
H29A1.196100.011400.239400.0570*
H29B1.247500.082900.176100.0570*
H29C1.128900.098600.242600.0570*
H30A1.148200.101600.141400.0610*
H30B1.051500.089600.077000.0610*
H30C1.200200.034900.074300.0610*
H330.567300.479400.222700.0320*
H350.847000.265500.215800.0290*
H38A0.525000.422600.101000.0880*0.706 (6)
H38B0.614600.499700.100300.0880*0.706 (6)
H38C0.627800.440500.027000.0880*0.706 (6)
H39A0.625800.273600.104500.0880*0.706 (6)
H39B0.725700.292700.029500.0880*0.706 (6)
H39C0.786800.246100.103700.0880*0.706 (6)
H40A0.876000.409700.033600.1040*0.706 (6)
H40B0.868100.463000.110100.1040*0.706 (6)
H40C0.936500.364100.108300.1040*0.706 (6)
H41A0.567500.252900.449700.0350*
H41B0.473100.339500.479500.0350*
H43A0.568500.180400.682500.1120*
H43B0.507400.276500.708900.1120*
H44A0.288500.245800.704000.1900*
H44B0.365900.180100.762500.1900*
H44C0.348700.149600.678700.1900*
H20B0.521700.094400.052000.0860*
H20C0.602000.173800.041700.0860*
H230.792200.026300.159600.0300*
H38D0.607000.390600.030600.0880*0.294 (6)
H38E0.549200.336800.103800.0880*0.294 (6)
H38F0.537400.439700.106300.0880*0.294 (6)
H39D0.906600.291200.100800.0880*0.294 (6)
H39E0.772900.246900.096200.0880*0.294 (6)
H39F0.828100.305400.025600.0880*0.294 (6)
H40D0.888100.451500.115700.1040*0.294 (6)
H40E0.813700.466000.039000.1040*0.294 (6)
H40F0.742900.510400.116700.1040*0.294 (6)
H45A1.016000.472300.384700.0580*0.500
H45B1.027400.568200.398300.0580*0.500
H46A0.824200.562100.346300.0860*0.500
H46B0.789200.500100.416100.0860*0.500
H46C0.800700.596900.429900.0860*0.500
H47A0.836400.434100.519200.0640*0.500
H47B0.943600.406600.576400.0640*0.500
H48A0.957400.288900.509100.1240*0.500
H48B0.990600.350400.438600.1240*0.500
H48C1.098900.322700.496400.1240*0.500
H49A1.194000.536800.496300.0570*0.500
H49B1.197600.440300.473500.0570*0.500
H50A1.283100.437800.598300.0860*0.500
H50B1.143400.497900.612800.0860*0.500
H50C1.147000.401800.590100.0860*0.500
H51A0.958500.566100.601200.0740*0.500
H51B0.837100.574100.550700.0740*0.500
H52A0.938800.708400.559200.1090*0.500
H52B1.080200.656500.529700.1090*0.500
H52C0.958800.664600.479300.1090*0.500
H53A0.669100.001200.456600.0610*0.500
H53B0.738400.080100.476200.0610*0.500
H54A0.543800.095000.552900.1110*0.500
H54B0.649600.048700.609000.1110*0.500
H54C0.553100.006700.571100.1110*0.500
H55A0.948200.016000.418400.0480*0.500
H55B0.887400.065100.393500.0480*0.500
H56A1.113100.106200.386700.0760*0.500
H56B1.107400.080000.472400.0760*0.500
H56C1.046000.162000.452900.0760*0.500
H57A0.744300.114300.590000.0590*0.500
H57B0.884100.157900.549700.0590*0.500
H58A0.645700.130400.476800.1110*0.500
H58B0.710100.221800.510900.1110*0.500
H58C0.789200.177400.438600.1110*0.500
H59A0.991000.037400.579000.0660*0.500
H59B0.852100.000800.619400.0660*0.500
H60A0.994900.101200.599000.1140*0.500
H60B1.014800.092100.509600.1140*0.500
H60C0.872400.130300.550800.1140*0.500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0270 (4)0.0264 (4)0.0338 (4)0.0025 (3)0.0098 (3)0.0108 (3)
S20.0183 (3)0.0311 (4)0.0337 (4)0.0034 (3)0.0026 (3)0.0076 (3)
S30.0261 (4)0.0219 (4)0.0398 (4)0.0045 (3)0.0103 (3)0.0027 (3)
S40.0283 (4)0.0246 (4)0.0256 (4)0.0011 (3)0.0120 (3)0.0050 (3)
O10.0325 (12)0.0235 (11)0.0329 (12)0.0009 (9)0.0131 (9)0.0028 (9)
O20.0257 (11)0.0308 (11)0.0260 (11)0.0056 (9)0.0031 (8)0.0020 (9)
O30.0237 (11)0.0381 (13)0.0315 (12)0.0001 (9)0.0073 (9)0.0104 (10)
O40.0282 (11)0.0304 (11)0.0211 (10)0.0054 (9)0.0057 (8)0.0046 (9)
O50.0498 (16)0.0520 (16)0.0312 (13)0.0028 (12)0.0157 (12)0.0062 (11)
O60.074 (2)0.088 (2)0.0310 (14)0.0394 (19)0.0065 (14)0.0145 (15)
C10.0211 (14)0.0274 (15)0.0228 (14)0.0013 (11)0.0012 (11)0.0021 (12)
C20.0238 (14)0.0259 (15)0.0246 (14)0.0004 (11)0.0039 (11)0.0052 (12)
C30.0275 (15)0.0260 (15)0.0267 (15)0.0002 (12)0.0018 (12)0.0065 (12)
C40.0292 (16)0.0295 (16)0.0235 (15)0.0019 (12)0.0035 (12)0.0020 (12)
C50.0235 (14)0.0348 (17)0.0232 (14)0.0015 (12)0.0032 (11)0.0056 (13)
C60.0191 (13)0.0296 (15)0.0222 (14)0.0001 (11)0.0003 (11)0.0062 (12)
C70.0416 (19)0.0319 (18)0.0344 (18)0.0027 (14)0.0114 (15)0.0031 (14)
C80.063 (3)0.047 (2)0.045 (2)0.003 (2)0.001 (2)0.0159 (19)
C90.046 (2)0.0301 (18)0.046 (2)0.0096 (15)0.0074 (17)0.0021 (16)
C100.076 (3)0.040 (2)0.064 (3)0.006 (2)0.044 (3)0.007 (2)
C110.0203 (14)0.0272 (15)0.0272 (15)0.0084 (11)0.0044 (11)0.0035 (12)
C120.0224 (14)0.0245 (15)0.0301 (16)0.0046 (11)0.0056 (12)0.0051 (12)
C130.0249 (15)0.0241 (15)0.0312 (16)0.0052 (11)0.0070 (12)0.0037 (12)
C140.0237 (14)0.0275 (15)0.0278 (15)0.0081 (12)0.0046 (12)0.0043 (12)
C150.0223 (14)0.0257 (15)0.0324 (16)0.0039 (11)0.0054 (12)0.0082 (13)
C160.0203 (13)0.0218 (14)0.0331 (16)0.0037 (11)0.0063 (12)0.0061 (12)
C170.0335 (17)0.0340 (17)0.0250 (15)0.0091 (13)0.0007 (13)0.0026 (13)
C180.059 (3)0.092 (4)0.0280 (19)0.037 (3)0.0103 (18)0.002 (2)
C190.095 (4)0.041 (2)0.039 (2)0.012 (2)0.001 (2)0.0055 (18)
C200.053 (3)0.073 (3)0.037 (2)0.008 (2)0.0066 (19)0.001 (2)
C210.0250 (15)0.0229 (14)0.0255 (15)0.0002 (11)0.0068 (12)0.0009 (12)
C220.0274 (15)0.0202 (14)0.0298 (15)0.0035 (11)0.0096 (12)0.0003 (12)
C230.0302 (15)0.0195 (14)0.0266 (15)0.0029 (11)0.0086 (12)0.0014 (12)
C240.0272 (15)0.0204 (14)0.0235 (14)0.0029 (11)0.0068 (12)0.0007 (11)
C250.0252 (14)0.0230 (14)0.0264 (15)0.0037 (11)0.0088 (12)0.0006 (12)
C260.0259 (15)0.0241 (15)0.0245 (14)0.0012 (11)0.0099 (12)0.0009 (12)
C270.0291 (16)0.0280 (16)0.0254 (15)0.0050 (12)0.0035 (12)0.0041 (12)
C280.0325 (17)0.0319 (17)0.0310 (16)0.0039 (13)0.0025 (13)0.0097 (14)
C290.0294 (17)0.045 (2)0.0373 (19)0.0058 (14)0.0070 (14)0.0130 (16)
C300.048 (2)0.041 (2)0.0344 (18)0.0198 (17)0.0075 (16)0.0053 (16)
C310.0215 (13)0.0255 (14)0.0206 (14)0.0057 (11)0.0050 (11)0.0046 (11)
C320.0230 (14)0.0223 (14)0.0295 (15)0.0031 (11)0.0060 (12)0.0053 (12)
C330.0284 (15)0.0237 (15)0.0298 (16)0.0031 (12)0.0088 (12)0.0015 (12)
C340.0262 (15)0.0275 (15)0.0258 (15)0.0083 (12)0.0038 (12)0.0005 (12)
C350.0225 (14)0.0275 (15)0.0238 (14)0.0044 (11)0.0014 (11)0.0048 (12)
C360.0190 (13)0.0237 (14)0.0260 (15)0.0030 (11)0.0059 (11)0.0031 (12)
C370.0381 (18)0.0396 (19)0.0251 (16)0.0082 (15)0.0059 (13)0.0025 (14)
C380.077 (4)0.062 (4)0.032 (2)0.016 (4)0.018 (2)0.006 (3)
C390.098 (5)0.050 (3)0.031 (2)0.008 (3)0.023 (3)0.007 (2)
C400.062 (4)0.118 (6)0.035 (3)0.042 (4)0.003 (3)0.013 (4)
C410.0308 (16)0.0349 (17)0.0216 (15)0.0069 (13)0.0037 (12)0.0011 (13)
C420.046 (2)0.0327 (18)0.0254 (16)0.0061 (15)0.0055 (14)0.0037 (13)
C430.120 (5)0.136 (6)0.037 (3)0.064 (5)0.020 (3)0.026 (3)
C440.137 (7)0.149 (8)0.073 (4)0.001 (6)0.037 (5)0.043 (5)
C38A0.077 (4)0.062 (4)0.032 (2)0.016 (4)0.018 (2)0.006 (3)
C39A0.098 (5)0.050 (3)0.031 (2)0.008 (3)0.023 (3)0.007 (2)
C40A0.062 (4)0.118 (6)0.035 (3)0.042 (4)0.003 (3)0.013 (4)
N10.037 (2)0.074 (3)0.029 (2)0.029 (2)0.0085 (17)0.020 (2)
C450.044 (4)0.069 (5)0.034 (3)0.013 (3)0.000 (3)0.016 (3)
C460.050 (4)0.069 (3)0.061 (4)0.020 (3)0.017 (3)0.012 (4)
C470.047 (4)0.076 (5)0.045 (4)0.035 (4)0.002 (3)0.008 (4)
C480.093 (7)0.092 (7)0.073 (7)0.039 (5)0.005 (5)0.034 (5)
C490.038 (4)0.066 (4)0.043 (4)0.023 (3)0.000 (3)0.008 (3)
C500.050 (4)0.069 (3)0.061 (4)0.020 (3)0.017 (3)0.012 (4)
C510.053 (4)0.084 (5)0.051 (4)0.021 (4)0.011 (3)0.036 (4)
C520.074 (6)0.080 (6)0.074 (7)0.030 (5)0.008 (5)0.040 (5)
N20.042 (3)0.032 (3)0.029 (3)0.002 (2)0.001 (2)0.008 (2)
C530.048 (5)0.038 (4)0.059 (5)0.006 (3)0.005 (4)0.014 (4)
C540.050 (4)0.054 (4)0.114 (7)0.003 (3)0.002 (4)0.003 (4)
C550.043 (4)0.046 (4)0.027 (3)0.004 (3)0.002 (3)0.009 (3)
C560.047 (7)0.060 (7)0.036 (6)0.008 (5)0.007 (5)0.006 (5)
C570.045 (3)0.042 (3)0.058 (3)0.008 (3)0.000 (3)0.015 (3)
C580.050 (4)0.054 (4)0.114 (7)0.003 (3)0.002 (4)0.003 (4)
C590.081 (7)0.051 (5)0.032 (4)0.001 (4)0.018 (4)0.001 (4)
C600.100 (14)0.050 (8)0.082 (12)0.011 (7)0.025 (10)0.015 (7)
Geometric parameters (Å, º) top
S1—C21.779 (3)C19—H19A0.9800
S1—C321.781 (3)C19—H19B0.9800
S2—C61.772 (3)C20—H20B0.9800
S2—C121.779 (3)C20—H20C0.9800
S3—C161.785 (3)C20—H20A0.9800
S3—C221.780 (3)C23—H230.9500
S4—C261.774 (3)C25—H250.9500
S4—C361.773 (3)C28—H28A0.9800
O1—C11.344 (4)C28—H28C0.9800
O2—C111.315 (4)C28—H28B0.9800
O3—C211.339 (4)C29—H29B0.9800
O4—C311.387 (3)C29—H29A0.9800
O4—C411.425 (4)C29—H29C0.9800
O5—C421.198 (5)C30—H30B0.9800
O6—C421.346 (5)C30—H30A0.9800
O6—C431.454 (6)C30—H30C0.9800
O1—H1A0.8700C33—H330.9500
O3—H3A0.8700C35—H350.9500
N1—C45i1.520 (4)C38—H38C0.9800
N1—C47i1.518 (6)C38—H38B0.9800
N1—C511.516 (6)C38—H38A0.9800
N1—C51i1.516 (6)C38A—H38E0.9800
N1—C451.520 (4)C38A—H38D0.9800
N1—C49i1.516 (3)C38A—H38F0.9800
N1—C471.518 (6)C39—H39C0.9800
N1—C491.516 (3)C39—H39A0.9800
N2—C571.518 (7)C39—H39B0.9800
N2—C591.518 (8)C39A—H39F0.9800
N2—C531.517 (7)C39A—H39D0.9800
N2—C551.516 (7)C39A—H39E0.9800
C1—C21.406 (4)C40—H40C0.9800
C1—C61.403 (4)C40—H40B0.9800
C2—C31.380 (4)C40—H40A0.9800
C3—C41.402 (4)C40A—H40F0.9800
C4—C51.396 (4)C40A—H40D0.9800
C4—C71.531 (5)C40A—H40E0.9800
C5—C61.398 (4)C41—H41B0.9900
C7—C91.535 (5)C41—H41A0.9900
C7—C81.520 (6)C43—H43A0.9900
C7—C101.523 (6)C43—H43B0.9900
C11—C121.421 (4)C44—H44A0.9800
C11—C161.414 (4)C44—H44B0.9800
C12—C131.386 (4)C44—H44C0.9800
C13—C141.392 (4)C45—C461.494 (12)
C14—C151.394 (4)C47—C481.494 (11)
C14—C171.538 (5)C49—C501.497 (12)
C15—C161.398 (4)C51—C521.495 (11)
C17—C201.522 (6)C45—H45A0.9600
C17—C181.527 (6)C45—H45B0.9600
C17—C191.529 (6)C46—H46B0.9600
C21—C221.402 (4)C46—H46C0.9600
C21—C261.413 (4)C46—H46A0.9600
C22—C231.399 (4)C47—H47A0.9600
C23—C241.392 (4)C47—H47B0.9600
C24—C251.401 (4)C48—H48C0.9600
C24—C271.533 (4)C48—H48A0.9600
C25—C261.385 (4)C48—H48B0.9600
C27—C281.529 (4)C49—H49B0.9600
C27—C301.533 (5)C49—H49A0.9600
C27—C291.527 (5)C50—H50A0.9600
C31—C321.394 (4)C50—H50B0.9600
C31—C361.388 (4)C50—H50C0.9600
C32—C331.393 (4)C51—H51A0.9600
C33—C341.392 (4)C51—H51B0.9600
C34—C371.533 (5)C52—H52B0.9600
C34—C351.393 (4)C52—H52C0.9600
C35—C361.400 (4)C52—H52A0.9600
C37—C401.502 (9)C53—C541.495 (12)
C37—C39A1.540 (15)C55—C561.495 (13)
C37—C40A1.549 (17)C57—C581.498 (12)
C37—C391.544 (7)C59—C601.494 (15)
C37—C381.549 (9)C53—H53A0.9700
C37—C38A1.478 (14)C53—H53B0.9700
C41—C421.506 (4)C54—H54A0.9800
C43—C441.453 (12)C54—H54B0.9800
C3—H30.9500C54—H54C0.9800
C5—H50.9500C55—H55A0.9600
C8—H8B0.9800C55—H55B1.0400
C8—H8C0.9800C56—H56A0.9600
C8—H8A0.9800C56—H56B0.9600
C9—H9C0.9800C56—H56C0.9600
C9—H9A0.9800C57—H57A0.9700
C9—H9B0.9800C57—H57B0.9700
C10—H10B0.9800C58—H58A0.9800
C10—H10A0.9800C58—H58B0.9800
C10—H10C0.9800C58—H58C0.9800
C13—H130.9500C59—H59A0.9400
C15—H150.9500C59—H59B0.9600
C18—H18B0.9800C60—H60A0.9600
C18—H18A0.9800C60—H60B0.9600
C18—H18C0.9800C60—H60C0.9600
C19—H19C0.9800
C2—S1—C3297.27 (15)H20A—C20—H20C109.00
C6—S2—C12105.11 (14)C22—C23—H23119.00
C16—S3—C22104.12 (14)C24—C23—H23119.00
C26—S4—C3698.04 (14)C24—C25—H25119.00
C31—O4—C41113.2 (2)C26—C25—H25119.00
C42—O6—C43115.8 (4)C27—C28—H28A109.00
C1—O1—H1A115.00C27—C28—H28B109.00
C21—O3—H3A116.00C27—C28—H28C110.00
C47—N1—C49112.9 (4)H28B—C28—H28C109.00
C47—N1—C51109.2 (3)H28A—C28—H28B109.00
C47—N1—C47i180.00H28A—C28—H28C109.00
C47—N1—C49i67.1 (4)C27—C29—H29C110.00
C45i—N1—C4773.0 (4)H29A—C29—H29B110.00
C45—N1—C51i69.4 (4)C27—C29—H29B109.00
C45i—N1—C4972.3 (3)H29A—C29—H29C109.00
C47i—N1—C4967.1 (4)C27—C29—H29A109.00
C49—N1—C49i180.00H29B—C29—H29C109.00
C49—N1—C51i70.7 (4)C27—C30—H30B109.00
C45i—N1—C5169.4 (4)H30A—C30—H30B110.00
C47—N1—C51i70.8 (3)C27—C30—H30C109.00
C49—N1—C51109.3 (4)H30B—C30—H30C109.00
C51—N1—C51i180.00H30A—C30—H30C109.00
C45i—N1—C47i107.0 (4)C27—C30—H30A109.00
C45i—N1—C49i107.7 (3)C32—C33—H33119.00
C45i—N1—C51i110.7 (4)C34—C33—H33119.00
C47i—N1—C49i112.9 (4)C36—C35—H35119.00
C47i—N1—C51i109.2 (3)C34—C35—H35119.00
C49i—N1—C51i109.3 (4)H38B—C38—H38C110.00
C49i—N1—C5170.7 (4)C37—C38—H38A109.00
C45—N1—C49i72.3 (3)H38A—C38—H38C109.00
C45—N1—C47i73.0 (4)C37—C38—H38B110.00
C45—N1—C47107.0 (4)H38A—C38—H38B109.00
C45—N1—C49107.7 (3)C37—C38—H38C109.00
C45—N1—C51110.7 (4)H38D—C38A—H38F109.00
C47i—N1—C5170.8 (3)H38E—C38A—H38F109.00
C45—N1—C45i180.00C37—C38A—H38D109.00
C53—N2—C57108.4 (4)C37—C38A—H38E109.00
C53—N2—C59110.9 (4)H38D—C38A—H38E110.00
C53—N2—C55107.0 (4)C37—C38A—H38F110.00
C55—N2—C57112.9 (4)H39A—C39—H39C109.00
C55—N2—C59109.4 (4)H39B—C39—H39C110.00
C57—N2—C59108.2 (4)H39A—C39—H39B109.00
O1—C1—C6123.6 (3)C37—C39—H39A109.00
C2—C1—C6117.9 (3)C37—C39—H39B109.00
O1—C1—C2118.5 (3)C37—C39—H39C109.00
C1—C2—C3120.7 (3)H39D—C39A—H39F109.00
S1—C2—C1120.2 (2)H39E—C39A—H39F109.00
S1—C2—C3119.1 (2)C37—C39A—H39E109.00
C2—C3—C4122.5 (3)C37—C39A—H39F109.00
C3—C4—C5116.4 (3)H39D—C39A—H39E110.00
C5—C4—C7123.8 (3)C37—C39A—H39D109.00
C3—C4—C7119.8 (3)H40A—C40—H40C110.00
C4—C5—C6122.3 (3)H40A—C40—H40B109.00
S2—C6—C1121.3 (2)C37—C40—H40C110.00
C1—C6—C5120.2 (3)C37—C40—H40A109.00
S2—C6—C5118.2 (2)H40B—C40—H40C109.00
C4—C7—C8108.8 (3)C37—C40—H40B109.00
C4—C7—C9109.2 (3)C37—C40A—H40F109.00
C8—C7—C9109.1 (3)H40D—C40A—H40F110.00
C8—C7—C10109.3 (3)C37—C40A—H40D109.00
C9—C7—C10108.6 (3)H40E—C40A—H40F109.00
C4—C7—C10111.9 (3)H40D—C40A—H40E109.00
O2—C11—C16122.7 (3)C37—C40A—H40E109.00
C12—C11—C16115.6 (3)C42—C41—H41A110.00
O2—C11—C12121.8 (3)O4—C41—H41A110.00
S2—C12—C11118.8 (2)O4—C41—H41B110.00
S2—C12—C13119.6 (2)H41A—C41—H41B108.00
C11—C12—C13121.3 (3)C42—C41—H41B110.00
C12—C13—C14122.7 (3)O6—C43—H43A110.00
C13—C14—C17120.9 (3)H43A—C43—H43B108.00
C15—C14—C17122.6 (3)C44—C43—H43B110.00
C13—C14—C15116.3 (3)O6—C43—H43B110.00
C14—C15—C16122.2 (3)C44—C43—H43A111.00
S3—C16—C11119.3 (2)C43—C44—H44A110.00
S3—C16—C15119.1 (2)H44A—C44—H44B109.00
C11—C16—C15121.3 (3)C43—C44—H44B109.00
C14—C17—C19110.3 (3)C43—C44—H44C109.00
C18—C17—C20109.0 (3)H44A—C44—H44C110.00
C18—C17—C19107.7 (4)H44B—C44—H44C109.00
C14—C17—C18109.4 (3)N1—C45—C46116.1 (5)
C19—C17—C20108.0 (3)N1—C47—C48116.1 (7)
C14—C17—C20112.2 (3)N1—C49—C50115.8 (5)
O3—C21—C22124.2 (3)N1—C51—C52115.8 (7)
C22—C21—C26117.3 (3)N1—C45—H45A111.00
O3—C21—C26118.5 (3)H45A—C45—H45B108.00
C21—C22—C23120.4 (3)C46—C45—H45B105.00
S3—C22—C23118.5 (2)N1—C45—H45B109.00
S3—C22—C21121.2 (2)C46—C45—H45A107.00
C22—C23—C24122.6 (3)C45—C46—H46A116.00
C25—C24—C27119.8 (3)H46A—C46—H46B109.00
C23—C24—C27123.4 (3)C45—C46—H46B105.00
C23—C24—C25116.7 (3)C45—C46—H46C107.00
C24—C25—C26121.8 (3)H46A—C46—H46C109.00
S4—C26—C25119.6 (2)H46B—C46—H46C109.00
S4—C26—C21119.1 (2)N1—C47—H47B108.00
C21—C26—C25121.2 (3)N1—C47—H47A109.00
C24—C27—C29110.4 (3)C48—C47—H47A117.00
C24—C27—C30108.7 (3)C48—C47—H47B97.00
C29—C27—C30109.3 (3)H47A—C47—H47B108.00
C28—C27—C29108.9 (3)H48A—C48—H48B109.00
C24—C27—C28111.9 (2)H48A—C48—H48C109.00
C28—C27—C30107.7 (3)H48B—C48—H48C110.00
O4—C31—C32120.6 (3)C47—C48—H48A113.00
O4—C31—C36119.9 (3)C47—C48—H48B97.00
C32—C31—C36119.5 (3)C47—C48—H48C118.00
S1—C32—C33120.3 (2)C50—C49—H49A105.00
C31—C32—C33120.0 (3)N1—C49—H49A113.00
S1—C32—C31119.6 (2)N1—C49—H49B111.00
C32—C33—C34121.4 (3)C50—C49—H49B101.00
C35—C34—C37120.0 (3)H49A—C49—H49B110.00
C33—C34—C37122.2 (3)C49—C50—H50B97.00
C33—C34—C35117.8 (3)C49—C50—H50A129.00
C34—C35—C36121.5 (3)H50A—C50—H50B109.00
C31—C36—C35119.7 (3)H50A—C50—H50C109.00
S4—C36—C31119.5 (2)C49—C50—H50C101.00
S4—C36—C35120.7 (2)H50B—C50—H50C109.00
C34—C37—C38A109.8 (7)C52—C51—H51A98.00
C38A—C37—C40A111.3 (10)C52—C51—H51B116.00
C34—C37—C40109.6 (4)N1—C51—H51A111.00
C39A—C37—C40A109.2 (9)N1—C51—H51B105.00
C38A—C37—C39A108.0 (9)H51A—C51—H51B110.00
C34—C37—C39108.8 (3)H52B—C52—H52C109.00
C38—C37—C40109.9 (5)C51—C52—H52A118.00
C34—C37—C39A112.6 (6)C51—C52—H52B114.00
C38—C37—C39104.4 (5)C51—C52—H52C96.00
C34—C37—C40A106.0 (7)H52A—C52—H52B109.00
C39—C37—C40111.6 (5)H52A—C52—H52C109.00
C34—C37—C38112.5 (4)N2—C53—C54116.3 (6)
O4—C41—C42108.1 (3)N2—C55—C56116.3 (6)
O6—C42—C41108.4 (3)N2—C57—C58115.4 (6)
O5—C42—O6125.3 (3)N2—C59—C60116.0 (8)
O5—C42—C41126.3 (3)N2—C53—H53A109.00
O6—C43—C44107.0 (6)N2—C53—H53B108.00
C4—C3—H3119.00C54—C53—H53A107.00
C2—C3—H3119.00C54—C53—H53B109.00
C4—C5—H5119.00H53A—C53—H53B108.00
C6—C5—H5119.00C53—C54—H54A110.00
C7—C8—H8C109.00C53—C54—H54B109.00
H8A—C8—H8B109.00C53—C54—H54C110.00
C7—C8—H8B110.00H54A—C54—H54B109.00
C7—C8—H8A109.00H54A—C54—H54C109.00
H8B—C8—H8C109.00H54B—C54—H54C109.00
H8A—C8—H8C109.00N2—C55—H55A109.00
H9A—C9—H9C109.00N2—C55—H55B112.00
H9B—C9—H9C109.00C56—C55—H55A114.00
C7—C9—H9A109.00C56—C55—H55B100.00
C7—C9—H9B109.00H55A—C55—H55B105.00
H9A—C9—H9B109.00C55—C56—H56A112.00
C7—C9—H9C109.00C55—C56—H56B101.00
C7—C10—H10A109.00C55—C56—H56C115.00
C7—C10—H10B109.00H56A—C56—H56B109.00
H10B—C10—H10C109.00H56A—C56—H56C110.00
H10A—C10—H10C109.00H56B—C56—H56C109.00
C7—C10—H10C109.00N2—C57—H57A110.00
H10A—C10—H10B109.00N2—C57—H57B106.00
C14—C13—H13119.00C58—C57—H57A110.00
C12—C13—H13119.00C58—C57—H57B107.00
C14—C15—H15119.00H57A—C57—H57B108.00
C16—C15—H15119.00C57—C58—H58A109.00
H18B—C18—H18C109.00C57—C58—H58B109.00
C17—C18—H18B110.00C57—C58—H58C110.00
C17—C18—H18A109.00H58A—C58—H58B109.00
H18A—C18—H18C109.00H58A—C58—H58C109.00
C17—C18—H18C109.00H58B—C58—H58C110.00
H18A—C18—H18B109.00N2—C59—H59A108.00
C17—C19—H19A110.00N2—C59—H59B106.00
C17—C19—H19B109.00C60—C59—H59A108.00
C17—C19—H19C109.00C60—C59—H59B112.00
H19A—C19—H19B110.00H59A—C59—H59B107.00
H19A—C19—H19C109.00C59—C60—H60A105.00
H19B—C19—H19C110.00C59—C60—H60B114.00
C17—C20—H20C110.00C59—C60—H60C109.00
H20A—C20—H20B109.00H60A—C60—H60B110.00
C17—C20—H20B110.00H60A—C60—H60C110.00
C17—C20—H20A109.00H60B—C60—H60C109.00
H20B—C20—H20C109.00
C32—S1—C2—C158.5 (3)C7—C4—C5—C6179.3 (3)
C32—S1—C2—C3122.2 (3)C3—C4—C7—C860.4 (4)
C2—S1—C32—C31131.5 (3)C3—C4—C7—C958.5 (4)
C2—S1—C32—C3344.0 (3)C3—C4—C7—C10178.8 (3)
C12—S2—C6—C170.3 (3)C4—C5—C6—C10.2 (5)
C12—S2—C6—C5115.7 (3)C4—C5—C6—S2174.3 (2)
C6—S2—C12—C1197.0 (3)O2—C11—C16—S313.7 (4)
C6—S2—C12—C1389.8 (3)C16—C11—C12—C137.6 (4)
C22—S3—C16—C1192.9 (3)O2—C11—C12—S214.5 (4)
C22—S3—C16—C1592.8 (3)O2—C11—C12—C13172.4 (3)
C16—S3—C22—C2172.0 (3)C16—C11—C12—S2165.4 (2)
C16—S3—C22—C23109.9 (3)C12—C11—C16—C157.9 (4)
C36—S4—C26—C2166.2 (3)O2—C11—C16—C15172.2 (3)
C36—S4—C26—C25110.6 (3)C12—C11—C16—S3166.3 (2)
C26—S4—C36—C31136.8 (3)S2—C12—C13—C14171.6 (2)
C26—S4—C36—C3538.7 (3)C11—C12—C13—C141.4 (5)
C41—O4—C31—C3290.6 (3)C12—C13—C14—C17179.8 (3)
C41—O4—C31—C3690.8 (3)C12—C13—C14—C154.8 (5)
C31—O4—C41—C42161.1 (2)C13—C14—C15—C164.5 (5)
C43—O6—C42—O51.7 (6)C17—C14—C15—C16179.8 (3)
C43—O6—C42—C41179.7 (4)C15—C14—C17—C19140.0 (4)
C42—O6—C43—C44177.2 (5)C15—C14—C17—C2019.5 (4)
C49i—N1—C45—C467.3 (9)C13—C14—C17—C20165.4 (3)
C51i—N1—C45—C46126.7 (10)C13—C14—C17—C1873.5 (4)
C45—N1—C47—C4872.4 (9)C13—C14—C17—C1944.9 (4)
C49—N1—C47—C4846.0 (9)C15—C14—C17—C18101.6 (4)
C51—N1—C47—C48167.8 (9)C14—C15—C16—S3172.2 (2)
C45i—N1—C47—C48107.6 (9)C14—C15—C16—C112.0 (5)
C49i—N1—C47—C48134.0 (9)C26—C21—C22—C232.8 (4)
C51i—N1—C47—C4812.2 (9)O3—C21—C26—C25177.7 (3)
C45—N1—C49—C50171.5 (9)C22—C21—C26—S4174.2 (2)
C47—N1—C49—C5053.6 (10)O3—C21—C26—S45.6 (4)
C51—N1—C49—C5068.3 (9)O3—C21—C22—S30.7 (4)
C45i—N1—C49—C508.5 (9)O3—C21—C22—C23177.5 (3)
C47i—N1—C49—C50126.5 (10)C26—C21—C22—S3179.1 (2)
C51i—N1—C49—C50111.7 (9)C22—C21—C26—C252.5 (4)
C45—N1—C51—C5259.0 (9)S3—C22—C23—C24178.7 (2)
C47—N1—C51—C52176.5 (8)C21—C22—C23—C240.6 (5)
C49—N1—C51—C5259.5 (8)C22—C23—C24—C27177.9 (3)
C45i—N1—C51—C52121.0 (9)C22—C23—C24—C252.0 (4)
C47i—N1—C51—C523.5 (8)C23—C24—C25—C262.3 (4)
C49i—N1—C51—C52120.5 (8)C27—C24—C25—C26178.4 (3)
C47—N1—C45—C4665.6 (10)C25—C24—C27—C3063.8 (4)
C49—N1—C45—C46172.7 (9)C25—C24—C27—C2956.0 (4)
C51—N1—C45—C4653.3 (10)C23—C24—C27—C286.8 (4)
C47i—N1—C45—C46114.4 (10)C23—C24—C27—C29128.2 (3)
C57—N2—C55—C5654.4 (8)C23—C24—C27—C30112.0 (3)
C59—N2—C55—C5666.2 (7)C25—C24—C27—C28177.4 (3)
C53—N2—C57—C5860.9 (7)C24—C25—C26—S4176.7 (2)
C55—N2—C53—C54179.4 (6)C24—C25—C26—C210.0 (5)
C57—N2—C53—C5458.6 (7)O4—C31—C32—C33175.2 (3)
C59—N2—C53—C5460.1 (7)O4—C31—C32—S19.3 (4)
C53—N2—C55—C56173.6 (6)C32—C31—C36—C353.0 (4)
C57—N2—C59—C60177.0 (9)O4—C31—C36—S48.9 (4)
C55—N2—C59—C6059.7 (10)C36—C31—C32—S1172.1 (2)
C55—N2—C57—C5857.5 (7)C36—C31—C32—C333.4 (5)
C59—N2—C57—C58178.7 (6)O4—C31—C36—C35175.6 (3)
C53—N2—C59—C6058.2 (10)C32—C31—C36—S4172.5 (2)
C6—C1—C2—S1176.9 (2)S1—C32—C33—C34172.9 (2)
C6—C1—C2—C33.7 (4)C31—C32—C33—C342.6 (5)
O1—C1—C6—S21.1 (4)C32—C33—C34—C351.2 (5)
O1—C1—C2—C3174.6 (3)C32—C33—C34—C37178.3 (3)
O1—C1—C2—S14.7 (4)C33—C34—C37—C3814.1 (5)
C2—C1—C6—S2177.1 (2)C33—C34—C37—C39129.2 (5)
C2—C1—C6—C53.3 (4)C33—C34—C37—C40108.4 (5)
O1—C1—C6—C5175.0 (3)C33—C34—C35—C360.8 (5)
C1—C2—C3—C41.1 (5)C37—C34—C35—C36178.7 (3)
S1—C2—C3—C4179.5 (2)C35—C34—C37—C3950.3 (5)
C2—C3—C4—C7179.0 (3)C35—C34—C37—C4072.0 (5)
C2—C3—C4—C51.9 (5)C35—C34—C37—C38165.4 (4)
C5—C4—C7—C8116.4 (4)C34—C35—C36—C311.8 (5)
C5—C4—C7—C9124.7 (3)C34—C35—C36—S4173.8 (2)
C5—C4—C7—C104.4 (5)O4—C41—C42—O6163.3 (3)
C3—C4—C5—C62.4 (5)O4—C41—C42—O515.3 (4)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···S20.872.673.093 (2)111
O1—H1A···O20.871.752.607 (3)166
O3—H3A···S30.872.723.104 (2)108
O3—H3A···O20.871.692.539 (3)166
C3—H3···O5ii0.952.573.347 (4)139
C41—H41A···O30.992.483.444 (4)165
C52—H52B···O4i0.962.603.544 (16)169
C57—H57A···O2iii0.972.303.158 (7)147
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1.
 

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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