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Crystal structure of 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)

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, eMedical Laboratory Department, College of Science, Majmaah University, 11932, Saudi Arabia, fChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and gKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 8 September 2015; accepted 5 October 2015; online 10 October 2015)

The asymmetric unit of the title compound, C48H54O5S4·N(C2H5)4+·Cl, contains two tetra-tert-butyl-[(benzo­yl)meth­oxy]-trihy­droxy-tetra­thia­calix[4]arene mol­ecules, two tetra­ethyl­ammonium cations and two chloride anions. The two calixarene molecules in the asymmetric unit each display a cone conformation. There are no significant differences between the two independent molecules. The guest species do not sit within the calixarene `buckets'. In the crystal, extensive O—H⋯O, O—H⋯S and O—H⋯Cl hydrogen bonds and weak C—H⋯O, C—H⋯S and C—H⋯Cl inter­actions link the thia­calixarene mol­ecules, tetra­ethyl­ammonium cations and chloride anions, forming a three-dimensional network encompassing channels running parallel to the a-axis direction. The structure contains a solvent-accessible void of 76 (3) Å3, but no solvent mol­ecule could reasonably be located. The crystal studied was an inversion twin with a 0.57 (8):0.43 (8) domain ratio.

1. Related literature

For chemistry background and applications of thia­calixarenes, see: Gutsche (1998[Gutsche, C. D. (1998). Calixarenes Revisited. Monographs in Supramolecular Chemistry, edited by J. F. Stoddart. London: RSC.]); Shokova & Kovalev (2003[Shokova, E. A. & Kovalev, V. V. (2003). Russ. J. Org. Chem. 39, 1-28.]); Stoikov et al. (2003[Stoikov, I. I., Omran, O. A., Solovieva, S. E., Latypov, S. K., Enikeev, K. M., Gubaidullin, A. T., Antipin, I. S. & Konovalov, A. I. (2003). Tetrahedron, 59, 1469-1476.]); Agrawal & Pancholi (2007[Agrawal, Y. K. & Pancholi, J. P. (2007). Indian J. Chem. Sect. A, 46, 1377-1382.]); Ben Ali et al. (2001[Ben Ali, M., Lemiti, M., Jaffrezic-Renault, N., Martelet, C., Chovelon, J. M. & Ben Ouada, H. (2001). Thin Layer Films, 383, 292-295.]); Desroches et al. (2003[Desroches, C., Lopes, C., Kessler, V. & Parola, S. (2003). Dalton Trans. pp. 2085-2092.]); Higuchi et al. (2000[Higuchi, Y., Narita, M., Niimi, T., Ogawa, N., Hamada, F., Kumagai, H., Iki, N., Miyano, S. & Kabuto, C. (2000). Tetrahedron, 56, 4659-4666.]); Iki & Miyano (2001[Iki, N. & Miyano, S. (2001). J. Inclusion Phenom. Macrocyclic Chem. 41, 99-105.]); Morohashi et al. (2002[Morohashi, N., Iki, N. & Miyano, S. (2002). J. Syn. Org. Chem. Jpn, 60, 550-562.]); Odo et al. (2000[Odo, J., Kawahara, N., Inomata, Y., Inoue, A., Takeya, H., Miyanari, S. & Kumagai, H. (2000). Anal. Sci. 16, 963-966.], 2001[Odo, J., Inomata, Y., Takeya, H., Miyanari, S. & Kumagai, H. (2001). Anal. Sci. 17, 1425-1429.]); Omran & Anti­pin (2014[Omran, A. O. & Antipin, I. S. (2014). J. Incl Phenom. Macrocycl Chem. 78, 121-126.]). Many calixarene derivatives are being used in both environmental and biomedical monitoring, see: McMahon et al. (2003[McMahon, G., O'Malley, S., Nolan, K. & Diamond, D. (2003). Arkkivoc, vii, 23-31]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C48H54O5S4·C8H20N+·Cl

  • Mr = 1004.85

  • Monoclinic, P 21

  • a = 19.4338 (6) Å

  • b = 14.2147 (3) Å

  • c = 20.8631 (6) Å

  • β = 103.184 (3)°

  • V = 5611.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 293 K

  • 0.42 × 0.38 × 0.22 mm

2.2. Data collection

  • Agilent Xcalibur, Eos, Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.922, Tmax = 1.000

  • 40706 measured reflections

  • 25992 independent reflections

  • 18033 reflections with I > 2σ(I)

  • Rint = 0.035

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 0.241

  • S = 1.05

  • 25992 reflections

  • 1208 parameters

  • 8 restraints

  • H-atom parameters constrained

  • Δρmax = 0.98 e Å−3

  • Δρmin = −0.88 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Absolute structure parameter: 0.43 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯S2 0.82 2.61 3.110 (4) 121
O1—H1O⋯O2 0.82 1.85 2.581 (6) 147
O2—H2O⋯Cl2 0.82 2.30 3.048 (10) 152
O3—H3O⋯S3 0.82 2.57 3.077 (4) 121
O3—H3O⋯O2 0.82 1.91 2.567 (6) 136
O1′—H6O⋯S2′ 0.82 2.60 3.105 (4) 121
O1′—H6O⋯O2′ 0.82 1.85 2.580 (5) 147
O1′—H6O⋯Cl1i 0.82 2.81 3.338 (11) 124
O2′—H7O⋯Cl1i 0.82 2.27 3.006 (10) 150
O3′—H8O⋯S3′ 0.82 2.57 3.078 (4) 121
O3′—H8O⋯O2′ 0.82 1.90 2.567 (5) 138
C103—H10L⋯Cl2 0.97 2.43 3.397 (17) 174
C106—H10V⋯Cl2 0.96 2.64 3.382 (19) 135
C202—H20I⋯O5 0.96 2.58 3.459 (16) 152
C203—H20L⋯Cl1ii 0.97 2.41 3.373 (15) 173
C204—H20P⋯Cl2ii 0.96 2.78 3.63 (2) 147
C206—H20V⋯Cl1ii 0.96 2.55 3.353 (18) 141
C41—H41A⋯O3 0.97 2.45 3.318 (6) 149
C41—H41B⋯O1 0.97 2.46 3.253 (6) 139
C41′—H41C⋯S4′ 0.97 2.87 3.414 (6) 116
C41′—H41C⋯O3′ 0.97 2.45 3.313 (6) 148
C41′—H41D⋯O1′ 0.97 2.47 3.265 (6) 139
C44—H44⋯O2iii 0.93 2.54 3.431 (7) 160
C44′—H44′⋯O2′iv 0.93 2.57 3.447 (6) 158
C47—H47⋯O4v 0.93 2.55 3.368 (6) 146
C47—H47⋯O5v 0.93 2.45 3.255 (7) 145
C47′—H47′⋯O4′vi 0.93 2.57 3.380 (6) 146
C47′—H47′⋯O5′vi 0.93 2.47 3.277 (7) 145
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) x, y+1, z; (iii) [-x+2, y+{\script{1\over 2}}, -z+2]; (iv) [-x+1, y-{\script{1\over 2}}, -z]; (v) [-x+2, y-{\script{1\over 2}}, -z+2]; (vi) [-x+1, y+{\script{1\over 2}}, -z].

Data collection: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Calixarenes have been found to be an outstanding platform for creating attractive host molecules and have prominent host–guest recognition ability towards different ions. These macrocylic have been used for catalysis, molecular recognition or ion separtion and sensors (Gutsche, 1998; Shokova & Kovalev, 2003; Stoikov et al., 2003). Since the discovery of p-tert-butylthiacalixarene in 1997 as a calixarene analogy with some additional features because of sulfur bridging atom in its skeleton structure, it attracts much attention in research rather than the classical calixarenes and exhibits a wide range of applications in supramolecular chemistry (Iki & Miyano, 2001; Morohashi et al., 2002; Desroches et al., 2003; Odo et al., 2000; Odo et al., 2001; Ben Ali et al., 2001; Agrawal & Pancholi, 2007; Higuchi et al., 2000; Omran & Antipin, 2014). Many calixarene derivatives are being used in both environmental and biomedical monitoring (McMahon et al., 2003). Based on these findings we report here the synthesis and crystal structure of the title compound.

Two crystallographically independent molecules (A and B) in the asymmetric unit are shown in Figs 1 and 2, respectively, and together with two tetraethylammonium chloride molecules in Fig. 3. The bond lengths and bond angles of molecules A and B are within the normal ranges.

In the crystal structure, molecules are linked by C—H···O, C—H···S, C—H···Cl, O—H···O, O—H···S and O—H···Cl interactions, forming a three-dimensional network (Table 1). These lead to the formation of channels running parallel to the a-axis direction (Fig. 4).

Related literature top

For chemistry background and applications of thiacalixarenes, see: Gutsche (1998); Shokova & Kovalev (2003); Stoikov et al. (2003); Agrawal & Pancholi (2007); Ben Ali et al. (2001); Desroches et al. (2003); Higuchi et al. (2000); Iki & Miyano (2001); Morohashi et al. (2002); Odo et al. (2000, 2001); Omran & Antipin (2014). Many calixarene derivatives are being used in both environmental and biomedical monitoring, see: McMahon et al. (2003).

Experimental top

A mixture of p-tert-butylthiacalix[4]arene 1 g (1.38 mmol), anhydrous K2CO3 5.0 g, TEAB 0.4 g and phenacyl bromide 0.28–0.55 g (1.38–2.76 mmol) in 50 ml benzene was heated at 373 K for 48 h. the mixture was filtered and the benzene layer was evaporated to dryness. The solid residue was washed by diluted hydrochloric acid solution, extracted with methylene chloride. The methylene chloride layer was dried over magnesium sulfate then filtered and concentrated. The residue was treated with methyl alcohol to deposit a white solid product. The product was filtered off, dried under vacuum and recrystalized from a mixture of methylene chloride/methanol (1v/1v) to give colourless crystals suitable for X-ray diffraction in 90% yield.

Refinement top

All H atoms were positioned geometrically and constrained to ride on their parent atoms (C—H = 0.93, 0.96 and 0.97 Å, O—H = 0.82 Å). Uiso(H) values were set to a multiple of Ueq(C,O) with 1.5 for CH3 and OH, and 1.2 for CH and CH2. The (3 0 1), (4 0 8), (3 0 6), (-21 0 5), (1 4 0), (2 0 4), (-4 -9 22), (-4 -3 4), (1 0 8), (-12 5 3), (-2 0 10), (1 2 1), (-6 -3 6), (-4 3 4), (1 -4 0), (0 1 3), (3 0 0), (6 3 8) and (1 0 10) reflections were omitted owing to very bad agreement.

Structure description top

Calixarenes have been found to be an outstanding platform for creating attractive host molecules and have prominent host–guest recognition ability towards different ions. These macrocylic have been used for catalysis, molecular recognition or ion separtion and sensors (Gutsche, 1998; Shokova & Kovalev, 2003; Stoikov et al., 2003). Since the discovery of p-tert-butylthiacalixarene in 1997 as a calixarene analogy with some additional features because of sulfur bridging atom in its skeleton structure, it attracts much attention in research rather than the classical calixarenes and exhibits a wide range of applications in supramolecular chemistry (Iki & Miyano, 2001; Morohashi et al., 2002; Desroches et al., 2003; Odo et al., 2000; Odo et al., 2001; Ben Ali et al., 2001; Agrawal & Pancholi, 2007; Higuchi et al., 2000; Omran & Antipin, 2014). Many calixarene derivatives are being used in both environmental and biomedical monitoring (McMahon et al., 2003). Based on these findings we report here the synthesis and crystal structure of the title compound.

Two crystallographically independent molecules (A and B) in the asymmetric unit are shown in Figs 1 and 2, respectively, and together with two tetraethylammonium chloride molecules in Fig. 3. The bond lengths and bond angles of molecules A and B are within the normal ranges.

In the crystal structure, molecules are linked by C—H···O, C—H···S, C—H···Cl, O—H···O, O—H···S and O—H···Cl interactions, forming a three-dimensional network (Table 1). These lead to the formation of channels running parallel to the a-axis direction (Fig. 4).

For chemistry background and applications of thiacalixarenes, see: Gutsche (1998); Shokova & Kovalev (2003); Stoikov et al. (2003); Agrawal & Pancholi (2007); Ben Ali et al. (2001); Desroches et al. (2003); Higuchi et al. (2000); Iki & Miyano (2001); Morohashi et al. (2002); Odo et al. (2000, 2001); Omran & Antipin (2014). Many calixarene derivatives are being used in both environmental and biomedical monitoring, see: McMahon et al. (2003).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the molecule A of two molecules in the asymmetric unit with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. All H atoms are omitted for clarity.
[Figure 2] Fig. 2. View of the molecule B of two molecules in the asymmetric unit with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. All H atoms are omitted for clarity.
[Figure 3] Fig. 3. View of two molecules (A and B) with two solvent molecules in the asymmetric unit with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. All H atoms are omitted for clarity.
[Figure 4] Fig. 4. A view of the molecular packing down b axis. H atoms not involved in H bonding are omitted for clarity.
25-Benzoylmethoxy-5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-2,8,14,20-tetrathiacalix[4]arene–tetraethylammonium chloride (1/1) top
Crystal data top
C48H54O5S4·C8H20N+·ClF(000) = 2152
Mr = 1004.85Dx = 1.189 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9238 reflections
a = 19.4338 (6) Åθ = 3.2–31.7°
b = 14.2147 (3) ŵ = 0.26 mm1
c = 20.8631 (6) ÅT = 293 K
β = 103.184 (3)°Prism, colourless
V = 5611.4 (3) Å30.42 × 0.38 × 0.22 mm
Z = 4
Data collection top
Agilent Xcalibur, Eos, Gemini
diffractometer
25992 independent reflections
Radiation source: Enhance (Mo) X-ray Source18033 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 16.0416 pixels mm-1θmax = 32.8°, θmin = 3.1°
ω scansh = 2727
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 1921
Tmin = 0.922, Tmax = 1.000l = 3131
40706 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.079 w = 1/[σ2(Fo2) + (0.1278P)2 + 2.7781P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.241(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.98 e Å3
25992 reflectionsΔρmin = 0.88 e Å3
1208 parametersAbsolute structure: Flack (1983)
8 restraintsAbsolute structure parameter: 0.43 (8)
Crystal data top
C48H54O5S4·C8H20N+·ClV = 5611.4 (3) Å3
Mr = 1004.85Z = 4
Monoclinic, P21Mo Kα radiation
a = 19.4338 (6) ŵ = 0.26 mm1
b = 14.2147 (3) ÅT = 293 K
c = 20.8631 (6) Å0.42 × 0.38 × 0.22 mm
β = 103.184 (3)°
Data collection top
Agilent Xcalibur, Eos, Gemini
diffractometer
25992 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
18033 reflections with I > 2σ(I)
Tmin = 0.922, Tmax = 1.000Rint = 0.035
40706 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.241Δρmax = 0.98 e Å3
S = 1.05Δρmin = 0.88 e Å3
25992 reflectionsAbsolute structure: Flack (1983)
1208 parametersAbsolute structure parameter: 0.43 (8)
8 restraints
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*/Ueq
S10.80181 (8)0.70396 (10)0.81392 (7)0.0378 (4)
S20.79798 (8)0.32086 (9)0.76697 (7)0.0375 (4)
S31.08437 (7)0.32100 (10)0.78599 (7)0.0386 (3)
S41.08698 (7)0.70419 (9)0.83087 (6)0.0352 (3)
S1'0.39116 (7)0.32712 (10)0.18651 (6)0.0364 (3)
S2'0.41163 (7)0.70921 (10)0.23426 (7)0.0376 (4)
S3'0.68815 (7)0.70828 (10)0.21467 (7)0.0371 (3)
S4'0.66803 (7)0.32534 (9)0.16843 (6)0.0336 (3)
Cl10.5890 (5)0.1924 (8)0.9383 (4)0.272 (5)
O10.8589 (2)0.5115 (3)0.82787 (19)0.0398 (11)
O20.9501 (2)0.3800 (3)0.82638 (16)0.0332 (10)
O31.0475 (2)0.5057 (3)0.84746 (18)0.0393 (11)
O40.9539 (2)0.7408 (2)0.87704 (15)0.0354 (9)
O50.9786 (4)0.7796 (3)1.00075 (19)0.071 (2)
Cl20.8781 (5)0.3360 (8)0.9383 (4)0.269 (5)
C10.6904 (3)0.6073 (4)0.7405 (3)0.0373 (17)
O1'0.4415 (2)0.5191 (3)0.17254 (19)0.0386 (11)
C20.7589 (3)0.6001 (4)0.7784 (3)0.0345 (14)
O2'0.53388 (19)0.6500 (2)0.17442 (16)0.0316 (10)
C30.7947 (3)0.5140 (4)0.7881 (2)0.0323 (14)
O3'0.6206 (2)0.5239 (3)0.15314 (17)0.0370 (11)
C40.7594 (3)0.4353 (4)0.7545 (2)0.0336 (14)
O4'0.5115 (2)0.2898 (2)0.12228 (15)0.0319 (9)
C50.6911 (3)0.4432 (4)0.7169 (3)0.0367 (16)
O5'0.4777 (4)0.2509 (3)0.00141 (19)0.072 (2)
C60.6547 (3)0.5280 (4)0.7093 (3)0.0399 (17)
C70.5784 (4)0.5339 (5)0.6676 (3)0.0467 (17)
C80.5516 (6)0.6335 (8)0.6604 (7)0.119 (5)
C90.5321 (4)0.4741 (8)0.7010 (4)0.075 (3)
C100.5757 (6)0.4932 (11)0.5992 (5)0.105 (5)
C110.8604 (3)0.2973 (4)0.6625 (2)0.0331 (12)
C120.8709 (2)0.3240 (4)0.7288 (2)0.0283 (11)
C130.9400 (3)0.3436 (3)0.7676 (2)0.0290 (14)
C140.9963 (2)0.3213 (3)0.7379 (2)0.0292 (11)
C150.9840 (3)0.2946 (3)0.6716 (2)0.0318 (14)
C160.9163 (3)0.2858 (4)0.6318 (2)0.0311 (12)
C170.9045 (3)0.2603 (4)0.5588 (2)0.0402 (16)
C180.8299 (5)0.2777 (9)0.5210 (3)0.091 (4)
C190.9228 (5)0.1576 (6)0.5523 (4)0.069 (3)
C200.9535 (5)0.3218 (8)0.5270 (3)0.083 (3)
C211.1611 (3)0.4491 (4)0.7343 (3)0.0384 (17)
C221.1141 (3)0.4370 (4)0.7740 (2)0.0349 (14)
C231.0916 (3)0.5131 (4)0.8073 (2)0.0301 (11)
C241.1186 (3)0.6025 (4)0.7965 (2)0.0351 (12)
C251.1662 (3)0.6138 (4)0.7564 (3)0.0375 (16)
C261.1876 (3)0.5385 (4)0.7232 (3)0.0394 (17)
C271.2369 (4)0.5485 (5)0.6768 (3)0.0490 (19)
C281.1999 (5)0.5128 (8)0.6084 (4)0.077 (3)
C291.3035 (4)0.4928 (8)0.7018 (5)0.077 (3)
C301.2592 (8)0.6506 (7)0.6711 (7)0.114 (6)
C310.9866 (2)0.6758 (3)0.7159 (2)0.0258 (11)
C320.9990 (2)0.7007 (3)0.78212 (19)0.0243 (10)
C330.9425 (3)0.7144 (3)0.81181 (19)0.0277 (13)
C340.8743 (3)0.7014 (4)0.7749 (2)0.0278 (11)
C350.8624 (3)0.6776 (4)0.7084 (2)0.0298 (11)
C360.9189 (3)0.6639 (3)0.6779 (2)0.0271 (11)
C370.9057 (3)0.6351 (4)0.6048 (2)0.0340 (13)
C380.9711 (4)0.5952 (9)0.5879 (3)0.084 (4)
C390.8830 (6)0.7202 (7)0.5621 (3)0.079 (3)
C400.8473 (5)0.5604 (7)0.5886 (3)0.070 (3)
C410.9633 (3)0.6610 (3)0.9205 (2)0.0348 (14)
C420.9788 (3)0.6964 (4)0.9898 (2)0.0351 (13)
C430.9947 (3)0.6261 (3)1.0436 (2)0.0312 (14)
C441.0124 (3)0.6590 (4)1.1089 (2)0.0360 (14)
C451.0281 (4)0.5972 (4)1.1603 (2)0.0417 (18)
C461.0254 (4)0.5011 (4)1.1481 (3)0.0433 (18)
C471.0081 (4)0.4679 (4)1.0844 (3)0.0424 (16)
C480.9926 (3)0.5301 (4)1.0321 (2)0.0365 (14)
C1'0.3177 (3)0.4237 (4)0.2627 (3)0.0391 (16)
C2'0.3667 (3)0.4301 (4)0.2231 (3)0.0346 (14)
C3'0.3975 (3)0.5166 (4)0.2133 (2)0.0314 (12)
C4'0.3794 (3)0.5954 (4)0.2468 (3)0.0344 (12)
C5'0.3303 (3)0.5871 (4)0.2864 (3)0.0383 (17)
C6'0.2988 (3)0.5021 (4)0.2947 (3)0.0400 (17)
C7'0.2441 (4)0.4977 (5)0.3373 (4)0.052 (2)
C8'0.2295 (7)0.3968 (7)0.3541 (6)0.102 (5)
C9'0.1775 (4)0.5495 (8)0.3007 (4)0.073 (3)
C10'0.2704 (5)0.5479 (8)0.4020 (4)0.082 (3)
C11'0.5250 (3)0.7316 (4)0.3387 (3)0.0363 (16)
C12'0.5031 (3)0.7055 (4)0.2726 (2)0.0312 (11)
C13'0.5528 (3)0.6864 (3)0.2336 (2)0.0285 (12)
C14'0.6242 (2)0.7080 (4)0.2634 (2)0.0298 (11)
C15'0.6439 (3)0.7340 (4)0.3291 (3)0.0339 (12)
C16'0.5966 (3)0.7429 (4)0.3697 (3)0.0368 (14)
C17'0.6204 (4)0.7690 (5)0.4425 (3)0.0492 (18)
C18'0.5621 (6)0.7607 (10)0.4780 (4)0.096 (4)
C19'0.6451 (10)0.8685 (8)0.4470 (5)0.149 (7)
C20'0.6783 (6)0.6990 (11)0.4766 (4)0.116 (5)
C21'0.7901 (3)0.5798 (4)0.2654 (3)0.0337 (14)
C22'0.7226 (3)0.5926 (4)0.2258 (2)0.0311 (12)
C23'0.6846 (3)0.5165 (4)0.1927 (2)0.0283 (11)
C24'0.7168 (3)0.4263 (4)0.2027 (2)0.0321 (14)
C25'0.7840 (3)0.4154 (4)0.2423 (2)0.0332 (14)
C26'0.8225 (3)0.4916 (4)0.2757 (3)0.0353 (16)
C27'0.8948 (3)0.4798 (4)0.3216 (3)0.0407 (17)
C28'0.8932 (4)0.5136 (6)0.3901 (3)0.057 (2)
C29'0.9488 (4)0.5381 (7)0.2947 (4)0.063 (3)
C30'0.9196 (5)0.3764 (6)0.3288 (4)0.067 (3)
C31'0.6250 (3)0.3515 (3)0.2838 (2)0.0272 (11)
C32'0.6039 (2)0.3282 (3)0.2173 (2)0.0254 (11)
C33'0.5331 (2)0.3155 (3)0.18780 (19)0.0248 (10)
C34'0.4828 (2)0.3283 (4)0.2256 (2)0.0277 (11)
C35'0.5043 (3)0.3506 (4)0.2918 (2)0.0308 (11)
C36'0.5755 (3)0.3630 (4)0.3224 (2)0.0292 (11)
C37'0.5979 (3)0.3920 (4)0.3949 (2)0.0369 (15)
C38'0.6710 (5)0.4311 (9)0.4127 (4)0.089 (4)
C39'0.5951 (8)0.3079 (8)0.4373 (3)0.106 (5)
C40'0.5481 (5)0.4694 (9)0.4094 (4)0.098 (4)
C41'0.5008 (3)0.3695 (3)0.0793 (2)0.0317 (13)
C42'0.4819 (3)0.3344 (4)0.0099 (2)0.0343 (14)
C43'0.4714 (3)0.4048 (4)0.0438 (2)0.0312 (14)
C44'0.4567 (3)0.3710 (4)0.1090 (2)0.0372 (14)
C45'0.4467 (4)0.4330 (4)0.1606 (2)0.0439 (18)
C46'0.4517 (4)0.5298 (4)0.1485 (3)0.0426 (18)
C47'0.4655 (3)0.5623 (4)0.0849 (3)0.0427 (18)
C48'0.4762 (3)0.5000 (4)0.0325 (2)0.0356 (14)
N10.7316 (3)0.5160 (5)0.9884 (3)0.0496 (17)
C1010.6644 (5)0.5741 (8)0.9824 (6)0.091 (4)
C1020.6541 (8)0.6476 (10)0.9349 (10)0.148 (8)
C1030.7320 (7)0.4724 (9)0.9252 (5)0.098 (4)
C1040.6633 (9)0.4157 (13)0.8927 (6)0.148 (8)
C1050.7357 (8)0.4551 (14)1.0466 (6)0.179 (8)
C1060.7984 (10)0.3894 (17)1.0618 (7)0.200 (12)
C1070.7949 (7)0.5819 (12)1.0075 (7)0.119 (6)
C1080.8067 (9)0.6162 (19)1.0767 (9)0.202 (12)
N20.7630 (3)1.0163 (4)0.9884 (3)0.0482 (16)
C2010.8276 (4)0.9585 (7)0.9832 (5)0.073 (3)
C2020.8157 (7)0.8812 (9)0.9367 (9)0.137 (7)
C2030.7296 (5)1.0612 (8)0.9248 (4)0.080 (3)
C2040.7792 (8)1.1205 (12)0.8923 (6)0.133 (6)
C2050.7912 (5)1.0878 (9)1.0404 (5)0.107 (4)
C2060.7330 (8)1.1501 (13)1.0580 (7)0.168 (8)
C2070.7100 (6)0.9540 (11)1.0089 (6)0.103 (5)
C2080.7315 (7)0.9154 (16)1.0784 (8)0.173 (8)
H10.667900.665400.735700.0450*
H1O0.874400.457700.829500.0600*
H2O0.925900.351800.847600.0500*
H3O1.035900.450600.849500.0590*
H50.668800.389900.696000.0440*
H8A0.553400.659600.703200.1780*
H8B0.503700.634100.635100.1780*
H8C0.580700.670300.638400.1780*
H9A0.532700.499500.743800.1120*
H9B0.549800.410800.705500.1120*
H9C0.484500.474200.674900.1120*
H10A0.593100.429700.603500.1580*
H10B0.604600.530600.577400.1580*
H10C0.527800.493600.573900.1580*
H110.814600.287000.638300.0390*
H151.022600.282200.653500.0380*
H18A0.818200.342900.524600.1360*
H18B0.798000.239400.538700.1360*
H18C0.825800.262100.475500.1360*
H19A0.970500.146300.576100.1030*
H19B0.918500.142700.506600.1030*
H19C0.891200.118800.569900.1030*
H20A1.001800.312000.549800.1240*
H20B0.941500.386900.530000.1240*
H20C0.947700.304700.481600.1240*
H211.175800.396800.714200.0460*
H251.184200.673400.751700.0450*
H28A1.231200.519100.579100.1160*
H28B1.157900.549200.592100.1160*
H28C1.187400.447900.611200.1160*
H29A1.326600.514800.744900.1150*
H29B1.334600.500700.672400.1150*
H29C1.292000.427400.704100.1150*
H30A1.282400.673600.713800.1710*
H30B1.218200.688300.653800.1710*
H30C1.291100.654100.642200.1710*
H311.024900.667000.696800.0310*
H350.816300.670800.683900.0360*
H38A0.985800.540100.614000.1270*
H38B1.008100.641300.596800.1270*
H38C0.961000.578700.542100.1270*
H39A0.919500.767200.571700.1180*
H39B0.840200.745200.570900.1180*
H39C0.875000.702500.516600.1180*
H40A0.861200.506000.615800.1050*
H40B0.839900.542900.543100.1050*
H40C0.804300.585500.596900.1050*
H41A1.002200.622500.913500.0420*
H41B0.920800.622900.911800.0420*
H441.013400.723301.117100.0430*
H451.040700.619401.203300.0500*
H461.035200.458901.183100.0520*
H471.006900.403401.076600.0510*
H480.980700.507400.989100.0440*
H1'0.297300.365800.267700.0470*
H8A'0.212500.361900.314300.1520*
H8B'0.194600.396000.380000.1520*
H8C'0.272400.368600.378700.1520*
H9A'0.159100.519200.259200.1100*
H5'0.318700.640200.307700.0460*
H9B'0.189200.613600.293300.1100*
H9C'0.142700.548100.326700.1100*
H6O0.456100.572900.170700.0580*
H7O0.498300.676700.153800.0470*
H8O0.607700.579000.151600.0550*
H10D0.280400.612300.393900.1230*
H10E0.312700.517800.426100.1230*
H10F0.234900.545300.427300.1230*
H11'0.491100.741700.363000.0440*
H15'0.691400.746100.347000.0410*
H18D0.545400.696900.475500.1440*
H18E0.524000.801700.458000.1440*
H18F0.579300.778000.523300.1440*
H19D0.682900.875100.424600.2210*
H19E0.661700.885600.492400.2210*
H19F0.606700.909000.426800.2210*
H20D0.659500.636300.472400.1740*
H20E0.693600.714800.522400.1740*
H20F0.717700.702500.456100.1740*
H21'0.814600.632000.285800.0400*
H25'0.804300.355800.246900.0390*
H28D0.939200.506000.418700.0850*
H28E0.859400.477300.406700.0850*
H28F0.880000.578800.388400.0850*
H29D0.994700.531400.323300.0940*
H29E0.935100.603100.292400.0940*
H29F0.950100.516100.251400.0940*
H30D0.965400.372900.358200.1000*
H30E0.922200.352100.286500.1000*
H30F0.886500.339700.346200.1000*
H31'0.672800.359500.302900.0330*
H35'0.470400.357400.316500.0370*
H38D0.673600.486200.386700.1330*
H38E0.703800.384800.404200.1330*
H38F0.682700.447400.458500.1330*
H39D0.626400.260200.427800.1590*
H39E0.547700.283800.428400.1590*
H39F0.609500.325600.482800.1590*
H40D0.550900.523400.382400.1470*
H40E0.561900.486900.455000.1470*
H40F0.500400.446200.399800.1470*
H41C0.543600.407100.086300.0380*
H41D0.463000.408600.088000.0380*
H44'0.453700.306600.117000.0440*
H45'0.436600.410800.203600.0530*
H46'0.445800.572000.183400.0510*
H47'0.467600.626700.076900.0510*
H48'0.486600.522800.010400.0430*
H1QW0.765300.648801.082600.3040*
H10G0.624200.531900.971700.1090*
H10H0.664900.601601.025100.1090*
H10I0.611100.680500.935400.2220*
H10J0.651100.621300.891900.2220*
H10K0.693200.690600.945200.2220*
H10L0.772100.430100.931200.1180*
H10M0.738900.521300.894900.1180*
H10N0.668400.389500.851600.2220*
H10O0.623300.457200.884900.2220*
H10P0.656300.365900.921600.2220*
H10Q0.846400.658201.085700.3040*
H10R0.692800.417901.039900.2130*
H10S0.737200.494901.084700.2130*
H10T0.795700.350701.098800.2980*
H10U0.841200.425501.071900.2980*
H10V0.798000.350201.024200.2980*
H10W0.816000.563601.106300.3040*
H10Y0.836900.549201.001900.1430*
H10Z0.787600.635500.978000.1430*
H2QW0.773800.878801.082900.2600*
H20G0.862001.000600.971400.0880*
H20H0.848600.933201.026400.0880*
H20I0.859600.849400.938000.2050*
H20J0.797200.905200.893100.2050*
H20K0.782600.837900.948100.2050*
H20L0.691701.101500.931700.0960*
H20M0.708501.012300.894200.0960*
H20N0.752801.145800.851400.1990*
H20O0.816601.081400.884200.1990*
H20P0.799001.171100.921100.1990*
H20Q0.694300.876401.087000.2600*
H20R0.824801.127701.025400.1280*
H20S0.816401.055601.079800.1280*
H20T0.754101.194301.091600.2520*
H20U0.700001.111301.073800.2520*
H20V0.708701.183601.019500.2520*
H20W0.739900.966601.109200.2600*
H20Y0.700100.901500.978600.1230*
H20Z0.666400.989101.004800.1230*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0502 (7)0.0276 (6)0.0421 (6)0.0061 (6)0.0242 (5)0.0121 (6)
S20.0481 (7)0.0233 (5)0.0469 (7)0.0079 (6)0.0232 (6)0.0039 (6)
S30.0391 (6)0.0228 (5)0.0477 (7)0.0044 (6)0.0029 (5)0.0039 (6)
S40.0399 (6)0.0267 (5)0.0322 (5)0.0033 (5)0.0057 (4)0.0051 (5)
S1'0.0349 (6)0.0282 (6)0.0407 (6)0.0020 (6)0.0024 (5)0.0047 (5)
S2'0.0340 (6)0.0250 (6)0.0509 (7)0.0050 (5)0.0035 (5)0.0017 (6)
S3'0.0425 (6)0.0236 (5)0.0490 (7)0.0033 (6)0.0182 (5)0.0043 (6)
S4'0.0453 (6)0.0283 (6)0.0307 (5)0.0011 (6)0.0160 (5)0.0082 (5)
Cl10.269 (8)0.315 (11)0.201 (6)0.065 (9)0.013 (6)0.056 (7)
O10.046 (2)0.0318 (19)0.0434 (19)0.0051 (18)0.0139 (17)0.0103 (16)
O20.049 (2)0.0238 (16)0.0258 (15)0.0009 (16)0.0066 (14)0.0030 (13)
O30.053 (2)0.0269 (17)0.0362 (18)0.0054 (17)0.0062 (16)0.0052 (15)
O40.066 (2)0.0207 (15)0.0177 (13)0.0040 (17)0.0061 (14)0.0029 (12)
O50.158 (6)0.0225 (19)0.0256 (17)0.005 (3)0.008 (3)0.0005 (15)
Cl20.285 (9)0.313 (11)0.217 (6)0.072 (9)0.073 (6)0.024 (7)
C10.048 (3)0.031 (3)0.042 (3)0.000 (2)0.029 (2)0.003 (2)
O1'0.040 (2)0.0313 (19)0.045 (2)0.0028 (17)0.0109 (16)0.0065 (16)
C20.045 (3)0.029 (2)0.036 (2)0.007 (2)0.023 (2)0.008 (2)
O2'0.0395 (18)0.0229 (16)0.0308 (16)0.0003 (15)0.0046 (14)0.0044 (13)
C30.041 (3)0.031 (2)0.032 (2)0.010 (2)0.023 (2)0.0080 (19)
O3'0.045 (2)0.0293 (18)0.0340 (17)0.0031 (17)0.0033 (15)0.0058 (15)
C40.043 (3)0.028 (2)0.036 (2)0.007 (2)0.022 (2)0.005 (2)
O4'0.052 (2)0.0217 (15)0.0186 (13)0.0006 (15)0.0011 (13)0.0004 (12)
C50.049 (3)0.030 (3)0.036 (2)0.008 (2)0.020 (2)0.005 (2)
O5'0.155 (6)0.026 (2)0.0244 (17)0.008 (3)0.000 (2)0.0017 (16)
C60.053 (3)0.033 (3)0.040 (3)0.008 (3)0.024 (2)0.006 (2)
C70.054 (3)0.040 (3)0.045 (3)0.001 (3)0.009 (3)0.005 (3)
C80.096 (8)0.060 (6)0.161 (11)0.013 (6)0.051 (8)0.006 (7)
C90.049 (4)0.103 (7)0.074 (5)0.004 (5)0.017 (4)0.006 (5)
C100.086 (6)0.162 (12)0.062 (5)0.003 (8)0.004 (5)0.043 (7)
C110.037 (2)0.029 (2)0.033 (2)0.002 (2)0.0072 (18)0.0043 (19)
C120.037 (2)0.0188 (19)0.031 (2)0.003 (2)0.0117 (17)0.0015 (18)
C130.044 (3)0.016 (2)0.0256 (19)0.0004 (18)0.0050 (18)0.0030 (15)
C140.035 (2)0.0163 (18)0.034 (2)0.0021 (19)0.0032 (17)0.0014 (18)
C150.040 (3)0.022 (2)0.035 (2)0.001 (2)0.0122 (19)0.0015 (18)
C160.040 (2)0.028 (2)0.026 (2)0.003 (2)0.0091 (18)0.0025 (18)
C170.049 (3)0.040 (3)0.030 (2)0.005 (3)0.006 (2)0.004 (2)
C180.085 (6)0.146 (10)0.030 (3)0.046 (6)0.009 (3)0.018 (4)
C190.097 (6)0.059 (4)0.046 (3)0.017 (4)0.008 (4)0.020 (3)
C200.114 (7)0.101 (7)0.039 (3)0.014 (7)0.031 (4)0.001 (4)
C210.035 (3)0.032 (3)0.043 (3)0.003 (2)0.002 (2)0.003 (2)
C220.038 (3)0.025 (2)0.034 (2)0.003 (2)0.0076 (19)0.0024 (19)
C230.033 (2)0.026 (2)0.0250 (19)0.0000 (19)0.0063 (16)0.0010 (17)
C240.036 (2)0.028 (2)0.034 (2)0.002 (2)0.0070 (19)0.0021 (19)
C250.035 (3)0.030 (2)0.040 (3)0.000 (2)0.007 (2)0.000 (2)
C260.033 (3)0.036 (3)0.044 (3)0.002 (2)0.002 (2)0.002 (2)
C270.050 (3)0.044 (3)0.055 (4)0.001 (3)0.016 (3)0.001 (3)
C280.064 (5)0.112 (8)0.056 (4)0.007 (5)0.015 (4)0.005 (5)
C290.042 (4)0.104 (7)0.082 (5)0.007 (5)0.010 (4)0.003 (5)
C300.169 (12)0.052 (5)0.162 (11)0.030 (7)0.122 (10)0.013 (6)
C310.032 (2)0.026 (2)0.0192 (17)0.0020 (18)0.0052 (15)0.0003 (16)
C320.033 (2)0.0168 (18)0.0203 (16)0.0033 (18)0.0005 (14)0.0020 (15)
C330.049 (3)0.0166 (19)0.0166 (16)0.001 (2)0.0056 (16)0.0005 (15)
C340.037 (2)0.022 (2)0.0267 (18)0.001 (2)0.0123 (16)0.0022 (17)
C350.033 (2)0.030 (2)0.0246 (19)0.001 (2)0.0030 (16)0.0044 (17)
C360.036 (2)0.025 (2)0.0196 (17)0.0012 (19)0.0047 (16)0.0021 (16)
C370.037 (2)0.045 (3)0.0186 (18)0.000 (2)0.0036 (17)0.0048 (19)
C380.069 (5)0.147 (10)0.035 (3)0.012 (6)0.007 (3)0.036 (5)
C390.137 (8)0.071 (5)0.025 (3)0.002 (6)0.011 (4)0.007 (3)
C400.091 (6)0.080 (5)0.041 (3)0.040 (5)0.019 (4)0.026 (4)
C410.063 (3)0.019 (2)0.0212 (19)0.000 (2)0.007 (2)0.0022 (17)
C420.060 (3)0.023 (2)0.0207 (18)0.002 (2)0.0056 (19)0.0012 (17)
C430.047 (3)0.021 (2)0.026 (2)0.007 (2)0.0092 (19)0.0029 (17)
C440.061 (3)0.026 (2)0.0207 (19)0.001 (2)0.009 (2)0.0033 (18)
C450.070 (4)0.034 (3)0.021 (2)0.007 (3)0.010 (2)0.001 (2)
C460.065 (4)0.033 (3)0.032 (2)0.010 (3)0.011 (2)0.013 (2)
C470.072 (4)0.021 (2)0.035 (2)0.008 (3)0.014 (3)0.001 (2)
C480.056 (3)0.027 (2)0.028 (2)0.001 (2)0.013 (2)0.0021 (19)
C1'0.031 (2)0.037 (3)0.045 (3)0.001 (2)0.000 (2)0.007 (2)
C2'0.031 (2)0.032 (3)0.036 (2)0.001 (2)0.0024 (19)0.001 (2)
C3'0.024 (2)0.032 (2)0.033 (2)0.0054 (19)0.0044 (16)0.0002 (19)
C4'0.029 (2)0.032 (2)0.038 (2)0.004 (2)0.0013 (18)0.001 (2)
C5'0.039 (3)0.033 (3)0.040 (3)0.006 (2)0.003 (2)0.002 (2)
C6'0.039 (3)0.038 (3)0.041 (3)0.005 (2)0.005 (2)0.004 (2)
C7'0.052 (4)0.046 (3)0.061 (4)0.002 (3)0.021 (3)0.006 (3)
C8'0.152 (10)0.066 (6)0.120 (8)0.014 (7)0.100 (8)0.007 (6)
C9'0.047 (4)0.107 (7)0.070 (5)0.017 (5)0.021 (3)0.009 (5)
C10'0.087 (6)0.100 (7)0.068 (5)0.008 (6)0.037 (5)0.015 (5)
C11'0.043 (3)0.032 (3)0.034 (2)0.004 (2)0.009 (2)0.002 (2)
C12'0.033 (2)0.0198 (19)0.039 (2)0.003 (2)0.0045 (17)0.001 (2)
C13'0.037 (2)0.016 (2)0.032 (2)0.0019 (18)0.0066 (18)0.0036 (16)
C14'0.032 (2)0.0191 (19)0.039 (2)0.000 (2)0.0098 (17)0.0002 (19)
C15'0.035 (2)0.025 (2)0.039 (2)0.001 (2)0.0029 (19)0.004 (2)
C16'0.043 (3)0.030 (2)0.035 (2)0.004 (2)0.004 (2)0.002 (2)
C17'0.061 (4)0.049 (3)0.033 (2)0.003 (3)0.001 (2)0.009 (3)
C18'0.108 (7)0.139 (10)0.043 (4)0.016 (8)0.020 (4)0.015 (5)
C19'0.29 (2)0.080 (7)0.055 (5)0.045 (10)0.004 (8)0.028 (5)
C20'0.103 (7)0.171 (13)0.056 (5)0.055 (9)0.021 (5)0.019 (7)
C21'0.034 (2)0.033 (3)0.036 (2)0.003 (2)0.0121 (19)0.004 (2)
C22'0.038 (2)0.029 (2)0.030 (2)0.001 (2)0.0152 (19)0.0038 (19)
C23'0.038 (2)0.029 (2)0.0202 (17)0.001 (2)0.0113 (16)0.0022 (17)
C24'0.048 (3)0.027 (2)0.026 (2)0.001 (2)0.018 (2)0.0054 (18)
C25'0.045 (3)0.028 (2)0.031 (2)0.001 (2)0.018 (2)0.0020 (19)
C26'0.040 (3)0.035 (3)0.034 (2)0.001 (2)0.015 (2)0.003 (2)
C27'0.041 (3)0.043 (3)0.039 (3)0.003 (3)0.011 (2)0.008 (2)
C28'0.059 (4)0.069 (5)0.039 (3)0.001 (4)0.004 (3)0.005 (3)
C29'0.046 (4)0.085 (6)0.060 (4)0.003 (4)0.019 (3)0.000 (4)
C30'0.069 (5)0.049 (4)0.070 (5)0.020 (4)0.011 (4)0.007 (4)
C31'0.030 (2)0.029 (2)0.0218 (17)0.0049 (18)0.0041 (15)0.0021 (16)
C32'0.036 (2)0.0187 (18)0.0228 (17)0.0021 (19)0.0094 (15)0.0025 (16)
C33'0.040 (2)0.0149 (18)0.0179 (16)0.0010 (18)0.0031 (15)0.0005 (15)
C34'0.030 (2)0.023 (2)0.0277 (19)0.003 (2)0.0015 (15)0.0018 (18)
C35'0.034 (2)0.033 (2)0.0255 (19)0.001 (2)0.0068 (17)0.0017 (18)
C36'0.036 (2)0.030 (2)0.0212 (18)0.004 (2)0.0057 (17)0.0015 (17)
C37'0.043 (3)0.047 (3)0.0205 (19)0.001 (3)0.0068 (18)0.003 (2)
C38'0.067 (5)0.156 (11)0.040 (3)0.018 (6)0.004 (3)0.038 (5)
C39'0.201 (13)0.083 (7)0.026 (3)0.013 (8)0.012 (5)0.008 (4)
C40'0.079 (6)0.138 (9)0.066 (5)0.040 (6)0.007 (4)0.066 (6)
C41'0.052 (3)0.019 (2)0.0211 (18)0.002 (2)0.0021 (18)0.0002 (16)
C42'0.053 (3)0.024 (2)0.0237 (19)0.002 (2)0.0040 (19)0.0012 (17)
C43'0.044 (3)0.024 (2)0.0228 (19)0.006 (2)0.0019 (18)0.0019 (17)
C44'0.059 (3)0.028 (2)0.0201 (19)0.001 (2)0.000 (2)0.0028 (18)
C45'0.072 (4)0.036 (3)0.020 (2)0.005 (3)0.003 (2)0.001 (2)
C46'0.064 (4)0.030 (3)0.032 (2)0.004 (3)0.007 (2)0.010 (2)
C47'0.065 (4)0.024 (2)0.036 (3)0.002 (3)0.005 (2)0.003 (2)
C48'0.050 (3)0.027 (2)0.027 (2)0.005 (2)0.003 (2)0.0018 (19)
N10.051 (3)0.059 (3)0.047 (3)0.001 (3)0.028 (2)0.017 (3)
C1010.072 (6)0.092 (7)0.112 (8)0.020 (6)0.028 (5)0.040 (6)
C1020.119 (10)0.093 (9)0.248 (19)0.028 (8)0.076 (12)0.085 (11)
C1030.123 (9)0.105 (8)0.081 (6)0.043 (7)0.055 (6)0.039 (6)
C1040.158 (13)0.199 (17)0.094 (8)0.106 (13)0.042 (8)0.058 (10)
C1050.171 (12)0.29 (2)0.114 (9)0.168 (14)0.114 (9)0.145 (12)
C1060.202 (17)0.31 (3)0.110 (10)0.180 (19)0.083 (11)0.110 (14)
C1070.097 (8)0.145 (12)0.126 (9)0.001 (9)0.047 (7)0.010 (9)
C1080.129 (12)0.33 (3)0.164 (13)0.081 (16)0.067 (11)0.150 (18)
N20.034 (2)0.058 (3)0.046 (3)0.004 (2)0.0045 (19)0.017 (2)
C2010.053 (4)0.076 (5)0.086 (5)0.006 (4)0.006 (4)0.035 (5)
C2020.089 (8)0.090 (8)0.231 (16)0.011 (7)0.035 (9)0.077 (10)
C2030.068 (5)0.102 (7)0.060 (4)0.010 (5)0.005 (4)0.024 (5)
C2040.125 (10)0.161 (13)0.097 (8)0.059 (10)0.006 (7)0.051 (9)
C2050.079 (6)0.139 (10)0.081 (6)0.038 (6)0.028 (5)0.077 (7)
C2060.113 (9)0.219 (18)0.140 (11)0.091 (11)0.039 (8)0.127 (12)
C2070.069 (6)0.140 (11)0.102 (8)0.016 (7)0.026 (5)0.025 (8)
C2080.089 (8)0.29 (2)0.141 (12)0.002 (13)0.028 (8)0.129 (15)
Geometric parameters (Å, º) top
S1—C21.773 (6)C11'—C16'1.404 (9)
S1—C341.781 (6)C12'—C13'1.424 (8)
S2—C41.785 (6)C13'—C14'1.419 (7)
S2—C121.777 (4)C14'—C15'1.387 (7)
S3—C141.776 (4)C15'—C16'1.391 (9)
S3—C221.784 (6)C16'—C17'1.529 (9)
S4—C241.784 (6)C17'—C20'1.548 (15)
S4—C321.780 (4)C17'—C19'1.490 (14)
S1'—C34'1.782 (4)C17'—C18'1.493 (13)
S1'—C2'1.766 (6)C21'—C22'1.394 (8)
S2'—C12'1.776 (6)C21'—C26'1.397 (8)
S2'—C4'1.776 (6)C22'—C23'1.400 (8)
S3'—C14'1.776 (4)C23'—C24'1.421 (8)
S3'—C22'1.771 (6)C24'—C25'1.386 (8)
S4'—C24'1.778 (6)C25'—C26'1.407 (8)
S4'—C32'1.782 (4)C26'—C27'1.518 (9)
O1—C31.332 (7)C27'—C30'1.543 (10)
O2—C131.304 (5)C27'—C28'1.515 (9)
O3—C231.332 (7)C27'—C29'1.540 (10)
O4—C331.380 (5)C31'—C32'1.394 (6)
O4—C411.438 (5)C31'—C36'1.398 (8)
O5—C421.205 (7)C32'—C33'1.385 (6)
O1—H1O0.8200C33'—C34'1.401 (6)
O2—H2O0.8200C34'—C35'1.385 (6)
O3—H3O0.8200C35'—C36'1.397 (8)
C1—C61.404 (8)C36'—C37'1.532 (6)
C1—C21.388 (9)C37'—C38'1.491 (12)
O1'—C3'1.337 (7)C37'—C39'1.496 (11)
C2—C31.400 (8)C37'—C40'1.540 (13)
O2'—C13'1.312 (5)C41'—C42'1.496 (6)
C3—C41.412 (8)C42'—C43'1.481 (7)
O3'—C23'1.331 (7)C43'—C48'1.373 (8)
C4—C51.384 (8)C43'—C44'1.409 (6)
O4'—C33'1.384 (5)C44'—C45'1.370 (7)
O4'—C41'1.430 (5)C45'—C46'1.398 (8)
C5—C61.388 (8)C46'—C47'1.373 (9)
O5'—C42'1.209 (7)C47'—C48'1.385 (8)
C6—C71.541 (10)N1—C1051.479 (17)
C7—C101.530 (13)N1—C1071.525 (17)
C7—C91.518 (12)N1—C1011.526 (12)
C7—C81.504 (14)N1—C1031.459 (13)
C11—C121.404 (6)C1'—H1'0.9300
C11—C161.391 (8)C5'—H5'0.9300
C12—C131.428 (7)C8'—H8B'0.9600
C13—C141.411 (7)C8'—H8C'0.9600
C14—C151.401 (6)C8'—H8A'0.9600
C15—C161.392 (8)C9'—H9C'0.9600
C16—C171.531 (6)C9'—H9A'0.9600
C17—C201.549 (11)C9'—H9B'0.9600
C17—C181.505 (11)C10'—H10E0.9600
C17—C191.516 (10)C10'—H10F0.9600
C21—C221.377 (8)C10'—H10D0.9600
C21—C261.410 (8)C11'—H11'0.9300
C22—C231.408 (8)C15'—H15'0.9300
C23—C241.412 (8)C18'—H18D0.9600
C24—C251.391 (8)C18'—H18E0.9600
C25—C261.389 (8)C18'—H18F0.9600
C26—C271.516 (9)C19'—H19E0.9600
C27—C281.531 (11)C19'—H19F0.9600
C27—C301.527 (13)C19'—H19D0.9600
C27—C291.505 (12)C20'—H20D0.9600
C31—C361.383 (7)C20'—H20F0.9600
C31—C321.393 (6)C20'—H20E0.9600
C32—C331.392 (7)C21'—H21'0.9300
C33—C341.385 (8)C25'—H25'0.9300
C34—C351.395 (6)C28'—H28E0.9600
C35—C361.403 (8)C28'—H28F0.9600
C36—C371.543 (6)C28'—H28D0.9600
C37—C381.505 (10)C29'—H29D0.9600
C37—C401.535 (11)C29'—H29E0.9600
C37—C391.507 (10)C29'—H29F0.9600
C41—C421.495 (6)C30'—H30D0.9600
C42—C431.482 (6)C30'—H30E0.9600
C43—C481.385 (7)C30'—H30F0.9600
C43—C441.407 (6)C31'—H31'0.9300
C44—C451.366 (7)C35'—H35'0.9300
C45—C461.388 (8)C38'—H38D0.9600
C46—C471.378 (9)C38'—H38E0.9600
C47—C481.383 (8)C38'—H38F0.9600
C1—H10.9300C39'—H39F0.9600
O1'—H6O0.8200C39'—H39D0.9600
O2'—H7O0.8200C39'—H39E0.9600
O3'—H8O0.8200C40'—H40E0.9600
C5—H50.9300C40'—H40F0.9600
C8—H8A0.9600C40'—H40D0.9600
C8—H8B0.9600C41'—H41C0.9700
C8—H8C0.9600C41'—H41D0.9700
C9—H9B0.9600C44'—H44'0.9300
C9—H9A0.9600C45'—H45'0.9300
C9—H9C0.9600C46'—H46'0.9300
C10—H10C0.9600C47'—H47'0.9300
C10—H10B0.9600C48'—H48'0.9300
C10—H10A0.9600C101—C1021.42 (2)
C11—H110.9300C103—C1041.57 (2)
C15—H150.9300C105—C1061.51 (3)
C18—H18B0.9600C107—C1081.49 (2)
C18—H18A0.9600N2—C2051.496 (13)
C18—H18C0.9600N2—C2071.493 (15)
C19—H19B0.9600N2—C2011.525 (11)
C19—H19C0.9600N2—C2031.482 (11)
C19—H19A0.9600C101—H10G0.9700
C20—H20B0.9600C101—H10H0.9700
C20—H20A0.9600C102—H10J0.9600
C20—H20C0.9600C102—H10K0.9600
C21—H210.9300C102—H10I0.9600
C25—H250.9300C103—H10L0.9700
C28—H28A0.9600C103—H10M0.9700
C28—H28C0.9600C104—H10P0.9600
C28—H28B0.9600C104—H10N0.9600
C29—H29B0.9600C104—H10O0.9600
C29—H29C0.9600C105—H10S0.9700
C29—H29A0.9600C105—H10R0.9700
C30—H30C0.9600C106—H10T0.9600
C30—H30B0.9600C106—H10U0.9600
C30—H30A0.9600C106—H10V0.9600
C31—H310.9300C107—H10Y0.9700
C35—H350.9300C107—H10Z0.9700
C38—H38C0.9600C108—H10Q0.9600
C38—H38A0.9600C108—H10W0.9600
C38—H38B0.9600C108—H1QW0.9600
C39—H39C0.9600C201—C2021.449 (18)
C39—H39B0.9600C203—C2041.548 (19)
C39—H39A0.9600C205—C2061.55 (2)
C40—H40B0.9600C207—C2081.52 (2)
C40—H40A0.9600C201—H20G0.9700
C40—H40C0.9600C201—H20H0.9700
C41—H41B0.9700C202—H20I0.9600
C41—H41A0.9700C202—H20J0.9600
C44—H440.9300C202—H20K0.9600
C45—H450.9300C203—H20L0.9700
C46—H460.9300C203—H20M0.9700
C47—H470.9300C204—H20N0.9600
C48—H480.9300C204—H20O0.9600
C1'—C2'1.399 (9)C204—H20P0.9600
C1'—C6'1.391 (8)C205—H20R0.9700
C2'—C3'1.403 (8)C205—H20S0.9700
C3'—C4'1.407 (8)C206—H20T0.9600
C4'—C5'1.402 (9)C206—H20U0.9600
C5'—C6'1.383 (8)C206—H20V0.9600
C6'—C7'1.535 (10)C207—H20Y0.9700
C7'—C8'1.519 (13)C207—H20Z0.9700
C7'—C9'1.533 (12)C208—H2QW0.9600
C7'—C10'1.509 (12)C208—H20Q0.9600
C11'—C12'1.397 (7)C208—H20W0.9600
C2—S1—C3497.9 (3)C22'—C23'—C24'117.4 (5)
C4—S2—C12105.3 (3)C23'—C24'—C25'120.8 (5)
C14—S3—C22102.7 (2)S4'—C24'—C25'119.5 (4)
C24—S4—C3297.0 (2)S4'—C24'—C23'119.5 (4)
C2'—S1'—C34'97.7 (3)C24'—C25'—C26'122.1 (5)
C4'—S2'—C12'104.9 (3)C21'—C26'—C25'116.4 (5)
C14'—S3'—C22'102.5 (3)C21'—C26'—C27'121.1 (5)
C24'—S4'—C32'97.5 (2)C25'—C26'—C27'122.6 (5)
C33—O4—C41112.1 (3)C28'—C27'—C29'109.6 (6)
C3—O1—H1O110.00C28'—C27'—C30'106.5 (6)
C13—O2—H2O109.00C29'—C27'—C30'108.9 (6)
C23—O3—H3O109.00C26'—C27'—C30'113.0 (5)
C2—C1—C6120.9 (5)C26'—C27'—C28'110.2 (5)
S1—C2—C3119.8 (4)C26'—C27'—C29'108.7 (5)
C1—C2—C3121.8 (5)C32'—C31'—C36'121.1 (5)
S1—C2—C1118.4 (4)C31'—C32'—C33'120.7 (4)
O1—C3—C4124.6 (5)S4'—C32'—C33'119.8 (3)
O1—C3—C2118.5 (5)S4'—C32'—C31'119.3 (4)
C2—C3—C4116.9 (5)C32'—C33'—C34'118.9 (4)
S2—C4—C3120.6 (4)O4'—C33'—C34'119.8 (4)
C3—C4—C5120.8 (5)O4'—C33'—C32'121.3 (4)
S2—C4—C5118.2 (4)S1'—C34'—C33'119.6 (3)
C33'—O4'—C41'112.2 (3)S1'—C34'—C35'120.1 (4)
C4—C5—C6122.2 (5)C33'—C34'—C35'120.0 (4)
C5—C6—C7120.8 (5)C34'—C35'—C36'121.8 (5)
C1—C6—C5117.3 (5)C35'—C36'—C37'120.9 (5)
C1—C6—C7121.9 (5)C31'—C36'—C35'117.5 (4)
C8—C7—C9110.2 (8)C31'—C36'—C37'121.5 (5)
C6—C7—C9107.8 (5)C36'—C37'—C38'112.7 (5)
C6—C7—C10109.3 (7)C36'—C37'—C39'109.2 (5)
C8—C7—C10109.0 (9)C36'—C37'—C40'109.7 (5)
C9—C7—C10108.6 (8)C39'—C37'—C40'110.2 (7)
C6—C7—C8112.0 (7)C38'—C37'—C39'108.2 (8)
C12—C11—C16122.2 (5)C38'—C37'—C40'106.9 (7)
S2—C12—C11118.9 (4)O4'—C41'—C42'108.1 (4)
S2—C12—C13119.6 (3)O5'—C42'—C41'120.5 (4)
C11—C12—C13121.2 (4)O5'—C42'—C43'121.6 (4)
O2—C13—C14122.5 (5)C41'—C42'—C43'117.9 (4)
O2—C13—C12122.1 (5)C42'—C43'—C44'117.5 (5)
C12—C13—C14115.5 (4)C42'—C43'—C48'122.9 (4)
C13—C14—C15121.3 (4)C44'—C43'—C48'119.5 (4)
S3—C14—C13119.8 (3)C43'—C44'—C45'120.0 (5)
S3—C14—C15118.9 (4)C44'—C45'—C46'120.0 (4)
C14—C15—C16122.6 (5)C45'—C46'—C47'119.7 (5)
C11—C16—C15116.5 (4)C46'—C47'—C48'120.6 (5)
C15—C16—C17121.4 (5)C43'—C48'—C47'120.2 (4)
C11—C16—C17122.0 (5)C105—N1—C107104.8 (9)
C16—C17—C19109.4 (5)C101—N1—C107108.3 (8)
C16—C17—C20109.0 (5)C101—N1—C103109.7 (8)
C18—C17—C20107.2 (6)C101—N1—C105105.6 (9)
C16—C17—C18113.0 (5)C103—N1—C105118.9 (10)
C19—C17—C20109.0 (6)C103—N1—C107109.1 (8)
C18—C17—C19109.2 (7)C6'—C1'—H1'119.00
C22—C21—C26121.9 (5)C2'—C1'—H1'119.00
C21—C22—C23121.6 (5)C4'—C5'—H5'119.00
S3—C22—C21118.7 (4)C6'—C5'—H5'119.00
S3—C22—C23119.6 (4)H8A'—C8'—H8C'109.00
O3—C23—C24119.1 (5)C7'—C8'—H8A'110.00
O3—C23—C22124.5 (5)C7'—C8'—H8B'110.00
C22—C23—C24116.4 (5)C7'—C8'—H8C'109.00
S4—C24—C23119.4 (4)H8A'—C8'—H8B'109.00
C23—C24—C25121.5 (5)H8B'—C8'—H8C'109.00
S4—C24—C25119.1 (4)H9A'—C9'—H9C'110.00
C24—C25—C26121.8 (5)C7'—C9'—H9B'109.00
C21—C26—C25116.8 (5)H9B'—C9'—H9C'110.00
C21—C26—C27119.8 (5)C7'—C9'—H9A'109.00
C25—C26—C27123.4 (5)C7'—C9'—H9C'109.00
C26—C27—C28109.5 (6)H9A'—C9'—H9B'110.00
C26—C27—C29110.4 (6)C7'—C10'—H10E109.00
C26—C27—C30111.8 (7)C7'—C10'—H10D110.00
C28—C27—C29109.4 (7)H10D—C10'—H10F109.00
C28—C27—C30108.9 (8)C7'—C10'—H10F110.00
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C11—C12—C13—C148.8 (7)C24'—C25'—C26'—C27'177.2 (5)
S2—C12—C13—O215.9 (7)C24'—C25'—C26'—C21'1.7 (8)
C11—C12—C13—O2171.0 (5)C21'—C26'—C27'—C29'61.8 (8)
O2—C13—C14—S312.2 (6)C25'—C26'—C27'—C30'1.7 (8)
O2—C13—C14—C15171.0 (4)C25'—C26'—C27'—C28'120.6 (6)
C12—C13—C14—C158.7 (6)C21'—C26'—C27'—C28'58.3 (8)
C12—C13—C14—S3168.1 (4)C25'—C26'—C27'—C29'119.3 (6)
C13—C14—C15—C161.9 (7)C21'—C26'—C27'—C30'177.2 (6)
S3—C14—C15—C16174.9 (4)C36'—C31'—C32'—S4'174.1 (4)
C14—C15—C16—C17177.5 (5)C32'—C31'—C36'—C37'177.8 (5)
C14—C15—C16—C115.2 (7)C36'—C31'—C32'—C33'0.2 (7)
C11—C16—C17—C1817.2 (9)C32'—C31'—C36'—C35'0.2 (7)
C11—C16—C17—C19104.6 (7)S4'—C32'—C33'—C34'173.0 (4)
C15—C16—C17—C18165.6 (7)S4'—C32'—C33'—O4'7.6 (6)
C11—C16—C17—C20136.3 (6)C31'—C32'—C33'—O4'178.2 (4)
C15—C16—C17—C1972.5 (7)C31'—C32'—C33'—C34'1.3 (7)
C15—C16—C17—C2046.6 (8)O4'—C33'—C34'—S1'8.5 (6)
C26—C21—C22—S3179.2 (5)C32'—C33'—C34'—C35'1.9 (7)
C26—C21—C22—C232.0 (9)C32'—C33'—C34'—S1'172.1 (4)
C22—C21—C26—C252.5 (9)O4'—C33'—C34'—C35'177.6 (5)
C22—C21—C26—C27177.5 (6)C33'—C34'—C35'—C36'1.4 (8)
C21—C22—C23—C241.4 (7)S1'—C34'—C35'—C36'172.4 (4)
S3—C22—C23—C24178.6 (4)C34'—C35'—C36'—C31'0.4 (8)
C21—C22—C23—O3178.5 (5)C34'—C35'—C36'—C37'177.2 (5)
S3—C22—C23—O31.3 (7)C31'—C36'—C37'—C39'104.3 (8)
C22—C23—C24—C251.6 (7)C31'—C36'—C37'—C40'134.9 (6)
O3—C23—C24—C25178.3 (5)C31'—C36'—C37'—C38'16.0 (9)
C22—C23—C24—S4174.5 (4)C35'—C36'—C37'—C39'78.2 (9)
O3—C23—C24—S45.6 (6)C35'—C36'—C37'—C40'42.6 (8)
C23—C24—C25—C262.3 (9)C35'—C36'—C37'—C38'161.6 (7)
S4—C24—C25—C26173.8 (5)O4'—C41'—C42'—O5'0.4 (8)
C24—C25—C26—C27177.3 (6)O4'—C41'—C42'—C43'177.3 (5)
C24—C25—C26—C212.7 (9)O5'—C42'—C43'—C44'0.4 (9)
C21—C26—C27—C30179.6 (8)O5'—C42'—C43'—C48'179.7 (7)
C25—C26—C27—C29118.4 (8)C41'—C42'—C43'—C44'177.3 (5)
C21—C26—C27—C2961.6 (8)C41'—C42'—C43'—C48'2.0 (9)
C21—C26—C27—C2858.9 (8)C42'—C43'—C44'—C45'179.8 (6)
C25—C26—C27—C28121.1 (7)C48'—C43'—C44'—C45'0.6 (9)
C25—C26—C27—C300.4 (10)C42'—C43'—C48'—C47'179.7 (6)
C32—C31—C36—C350.1 (7)C44'—C43'—C48'—C47'1.1 (9)
C32—C31—C36—C37179.2 (4)C43'—C44'—C45'—C46'0.6 (10)
C36—C31—C32—C330.1 (7)C44'—C45'—C46'—C47'1.1 (11)
C36—C31—C32—S4174.0 (3)C45'—C46'—C47'—C48'1.6 (11)
C31—C32—C33—C341.1 (7)C46'—C47'—C48'—C43'1.6 (9)
C31—C32—C33—O4178.8 (4)C103—N1—C101—C10259.0 (13)
S4—C32—C33—O47.2 (6)C105—N1—C101—C102171.7 (12)
S4—C32—C33—C34173.0 (4)C107—N1—C101—C10259.9 (13)
C32—C33—C34—C351.9 (7)C101—N1—C103—C10451.6 (13)
O4—C33—C34—S18.0 (6)C105—N1—C103—C10470.0 (14)
C32—C33—C34—S1172.2 (4)C107—N1—C103—C104170.0 (11)
O4—C33—C34—C35178.0 (5)C101—N1—C105—C106179.2 (13)
C33—C34—C35—C361.7 (8)C103—N1—C105—C10655.6 (17)
S1—C34—C35—C36172.4 (4)C107—N1—C105—C10666.6 (16)
C34—C35—C36—C310.7 (7)C101—N1—C107—C10871.3 (15)
C34—C35—C36—C37178.4 (5)C103—N1—C107—C108169.4 (14)
C35—C36—C37—C4041.7 (7)C105—N1—C107—C10841.0 (17)
C31—C36—C37—C40137.3 (6)C203—N2—C201—C20260.6 (12)
C31—C36—C37—C3817.0 (8)C205—N2—C201—C202178.7 (10)
C31—C36—C37—C39102.9 (7)C207—N2—C201—C20259.9 (12)
C35—C36—C37—C38162.1 (6)C201—N2—C203—C20453.0 (11)
C35—C36—C37—C3978.0 (7)C205—N2—C203—C20463.3 (11)
O4—C41—C42—O53.1 (8)C207—N2—C203—C204173.9 (10)
O4—C41—C42—C43176.5 (5)C201—N2—C205—C206175.4 (9)
C41—C42—C43—C44177.2 (5)C203—N2—C205—C20664.0 (11)
C41—C42—C43—C483.0 (9)C207—N2—C205—C20657.6 (12)
O5—C42—C43—C48177.5 (7)C201—N2—C207—C20867.7 (14)
O5—C42—C43—C442.3 (10)C203—N2—C207—C208170.1 (12)
C44—C43—C48—C470.3 (9)C205—N2—C207—C20846.8 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···S20.822.613.110 (4)121
O1—H1O···O20.821.852.581 (6)147
O2—H2O···Cl20.822.303.048 (10)152
O2—H2O···S20.822.703.051 (4)108
O3—H3O···S30.822.573.077 (4)121
O3—H3O···O20.821.912.567 (6)136
O1—H6O···S20.822.603.105 (4)121
O1—H6O···O20.821.852.580 (5)147
O1—H6O···Cl1i0.822.813.338 (11)124
O2—H7O···S20.822.683.044 (4)109
O2—H7O···Cl1i0.822.273.006 (10)150
O3—H8O···S30.822.573.078 (4)121
O3—H8O···O20.821.902.567 (5)138
C103—H10L···Cl20.972.433.397 (17)174
C106—H10V···Cl20.962.643.382 (19)135
C202—H20I···O50.962.583.459 (16)152
C203—H20L···Cl1ii0.972.413.373 (15)173
C204—H20P···Cl2ii0.962.783.63 (2)147
C206—H20V···Cl1ii0.962.553.353 (18)141
C41—H41A···O30.972.453.318 (6)149
C41—H41B···O10.972.463.253 (6)139
C41—H41C···S40.972.873.414 (6)116
C41—H41C···O30.972.453.313 (6)148
C41—H41D···O10.972.473.265 (6)139
C44—H44···O2iii0.932.543.431 (7)160
C44—H44···O2iv0.932.573.447 (6)158
C47—H47···O4v0.932.553.368 (6)146
C47—H47···O5v0.932.453.255 (7)145
C47—H47···O4vi0.932.573.380 (6)146
C47—H47···O5vi0.932.473.277 (7)145
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y+1, z; (iii) x+2, y+1/2, z+2; (iv) x+1, y1/2, z; (v) x+2, y1/2, z+2; (vi) x+1, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···S20.82002.61003.110 (4)121.00
O1—H1O···O20.82001.85002.581 (6)147.00
O2—H2O···Cl20.82002.30003.048 (10)152.00
O3—H3O···S30.82002.57003.077 (4)121.00
O3—H3O···O20.82001.91002.567 (6)136.00
O1'—H6O···S2'0.82002.60003.105 (4)121.00
O1'—H6O···O2'0.82001.85002.580 (5)147.00
O1'—H6O···Cl1i0.82002.81003.338 (11)124.00
O2'—H7O···Cl1i0.82002.27003.006 (10)150.00
O3'—H8O···S3'0.82002.57003.078 (4)121.00
O3'—H8O···O2'0.82001.90002.567 (5)138.00
C103—H10L···Cl20.97002.43003.397 (17)174.00
C106—H10V···Cl20.96002.64003.382 (19)135.00
C202—H20I···O50.96002.58003.459 (16)152.00
C203—H20L···Cl1ii0.97002.41003.373 (15)173.00
C204—H20P···Cl2ii0.96002.78003.63 (2)147.00
C206—H20V···Cl1ii0.96002.55003.353 (18)141.00
C41—H41A···O30.97002.45003.318 (6)149.00
C41—H41B···O10.97002.46003.253 (6)139.00
C41'—H41C···S4'0.97002.87003.414 (6)116.00
C41'—H41C···O3'0.97002.45003.313 (6)148.00
C41'—H41D···O1'0.97002.47003.265 (6)139.00
C44—H44···O2iii0.93002.54003.431 (7)160.00
C44'—H44'···O2'iv0.93002.57003.447 (6)158.00
C47—H47···O4v0.93002.55003.368 (6)146.00
C47—H47···O5v0.93002.45003.255 (7)145.00
C47'—H47'···O4'vi0.93002.57003.380 (6)146.00
C47'—H47'···O5'vi0.93002.47003.277 (7)145.00
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y+1, z; (iii) x+2, y+1/2, z+2; (iv) x+1, y1/2, z; (v) x+2, y1/2, z+2; (vi) x+1, y+1/2, z.
 

Acknowledgements

The authors acknowledge support from the Deanship of Scientific Research, and thank Majmaah University for funding this work under project No. 1. JPJ would like to acknowledge the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

First citationAgilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.  Google Scholar
First citationAgrawal, Y. K. & Pancholi, J. P. (2007). Indian J. Chem. Sect. A, 46, 1377–1382.  Google Scholar
First citationBen Ali, M., Lemiti, M., Jaffrezic-Renault, N., Martelet, C., Chovelon, J. M. & Ben Ouada, H. (2001). Thin Layer Films, 383, 292–295.  Google Scholar
First citationDesroches, C., Lopes, C., Kessler, V. & Parola, S. (2003). Dalton Trans. pp. 2085–2092.  Web of Science CSD CrossRef Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGutsche, C. D. (1998). Calixarenes Revisited. Monographs in Supramolecular Chemistry, edited by J. F. Stoddart. London: RSC.  Google Scholar
First citationHiguchi, Y., Narita, M., Niimi, T., Ogawa, N., Hamada, F., Kumagai, H., Iki, N., Miyano, S. & Kabuto, C. (2000). Tetrahedron, 56, 4659–4666.  Web of Science CSD CrossRef CAS Google Scholar
First citationIki, N. & Miyano, S. (2001). J. Inclusion Phenom. Macrocyclic Chem. 41, 99–105.  Web of Science CrossRef CAS Google Scholar
First citationMcMahon, G., O'Malley, S., Nolan, K. & Diamond, D. (2003). Arkkivoc, vii, 23–31  Google Scholar
First citationMorohashi, N., Iki, N. & Miyano, S. (2002). J. Syn. Org. Chem. Jpn, 60, 550–562.  CrossRef CAS Google Scholar
First citationOdo, J., Inomata, Y., Takeya, H., Miyanari, S. & Kumagai, H. (2001). Anal. Sci. 17, 1425–1429.  Web of Science CrossRef PubMed CAS Google Scholar
First citationOdo, J., Kawahara, N., Inomata, Y., Inoue, A., Takeya, H., Miyanari, S. & Kumagai, H. (2000). Anal. Sci. 16, 963–966.  Web of Science CrossRef CAS Google Scholar
First citationOmran, A. O. & Antipin, I. S. (2014). J. Incl Phenom. Macrocycl Chem. 78, 121–126.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationShokova, E. A. & Kovalev, V. V. (2003). Russ. J. Org. Chem. 39, 1–28.  Web of Science CrossRef CAS Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoikov, I. I., Omran, O. A., Solovieva, S. E., Latypov, S. K., Enikeev, K. M., Gubaidullin, A. T., Antipin, I. S. & Konovalov, A. I. (2003). Tetrahedron, 59, 1469–1476.  Web of Science CSD CrossRef CAS Google Scholar

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