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

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ISSN: 2414-3146

[1–9-NαC]-Linusorb B3 (Cyclo­linopeptide A) di­methyl sulfoxide monosolvate

aDepartment of Plant Sciences, College of Agriculture and Bioresources, University of Saskatchewan, 51 Campus Dr., Saskatoon, Saskatchewan, S7N 5A8, Canada, bCanadian Light Source Inc., 44 Innovation Blvd., Saskatoon, Saskatchewan, S7N 3V4, Canada, and cGuangdong Saskatchewan Oilseed Joint Laboratory, Department of Food Science and Engineering, Jinan University, 601 Huangpu Avenue West, Guangdong, Guangzhou, 510632, People's Republic of China
*Correspondence e-mail: sarah.purdy@usask.ca

Edited by A. J. Lough, University of Toronto, Canada (Received 15 February 2020; accepted 6 March 2020; online 13 March 2020)

Crystals of the dimethyl sulfoxide (DMSO) solvate of [1–9-NαC]-linusorb B3 (Cyclo­linopeptide A; CLP-A; C57H84N9O9·C2H6OS), a cyclic polypeptide were obtained following peptide extraction and purification from flaxseed oil. There are four intramolecular N—H⋯O hydrogen bonds. In the crystal, the mol­ecules are linked in chains along the a axis by N—H⋯O hydrogen bonds. Each DMSO O atom accepts a hydrogen bond from an NH group at the Phe6 location in the CLP-A mol­ecule.

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

Structure description

The mol­ecular structure of the title compound is shown in Fig. 1[link]. The cyclic polypeptide or orbitide [1–9-NαC]-linusorb B3 (Cyclo­linopeptide A; CLP-A) has nine amino acids (Ile1–Leu2–Val3–Pro4–Pro5–Phe6–Phe7–Leu8–Ile9). The nomenclature and amino-acid numbering for orbitides was standardized by Craik et al. (2016[Craik, D. J., Shim, Y. Y., Göransson, U., Moss, G. P., Tan, N. H., Jadhav, P. D., Shen, J. H. & Reaney, M. J. T. (2016). Biopolymers, 106, 917-924.]). The title compound was first isolated from flax seed by Kaufmann & Tobschirbel (1959[Kaufmann, H. P. & Tobschirbel, A. (1959). Chem. Ber. 92, 2805-2809.]). The current method involves the use of silica gel chromatography to extract cyclic peptides from unrefined flaxseed oil, followed by isolation of the orbitide using high performance liquid chromatography (Reaney et al., 2013[Reaney, M. J. T., Burnet, P.-G., Jadhav, P. J., Okinyo-Owiti, D. P., Shen, J. & Shim, Y. Y. (2013). Patent WO 2013091070 A1.]). The isolated orbitide was then dissolved in dimethyl sulfoxide (DMSO) and stored under ambient conditions. The mol­ecule has four intra­molecular N—H⋯O hydrogen bonds, and the DMSO solvate mol­ecule is bound to the Phe6 amino acid by an N—H⋯O hydrogen bond (Table 1[link]). The packing is shown in Fig. 2[link]. The first crystal structure for CLP-A 2-propanol solvate was published by Di Blasio et al., 1989[Di Blasio, B., Rossi, F., Benedetti, E., Pavone, V., Pedone, C., Temussi, P. A., Zanotti, G. & Tancredi, T. (1989). J. Am. Chem. Soc. 111, 9089-9098.]), followed by the same compound in methanol/2-propanol (Matsumoto et al., 2002[Matsumoto, T., Shishido, A., Morita, H., Itokawa, H. & Takeya, K. (2002). Tetrahedron, 58, 5135-5140.]), methanol (Quail et al., 2009[Quail, J. W., Shen, J., Reaney, M. J. T. & Sammynaiken, R. (2009). Acta Cryst. E65, o1913-o1914.]), and in aceto­nitrile (Chitanda et al., 2016[Chitanda, J. M., Zhu, J., Mausberg, P., Burnett, P. G. & Reaney, M. J. T. (2016). IUCrData, 1, x161706.]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2N⋯O7 0.88 2.12 2.970 (3) 162
N3—H3N⋯O6 0.88 2.16 3.023 (3) 166
N4—H4N⋯O7 0.88 2.29 3.117 (3) 157
N5—H5N⋯O3i 0.88 2.38 3.094 (3) 139
N6—H6N⋯O8 0.88 2.16 2.926 (3) 145
N8—H8N⋯O1S 0.88 2.05 2.800 (3) 150
Symmetry code: (i) x+1, y, z.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at 50% probability level. The DMSO solvent mol­ecule is not shown.
[Figure 2]
Figure 2
View along the b axis showing crystal packing of the title compound. The hydrogen bonds are shown as dashed lines and H atoms have been omitted for clarity.

The compound, [1–9-NαC]-linusorb B3, has shown to induce potentially beneficial responses in living organisms. The biomolecular inter­action with human albumin has been reported by Rempel et al. (2010[Rempel, B., Gui, B., Maley, J., Reaney, M. & Sammynaiken, R. (2010). J. Biomed. Biotechnol. pp. 1-8.]). It has demonstrated cytoprotective activity in liver cells by inhibiting cholate uptake (Kessler et al., 1986[Kessler, H., Klein, M., Müller, A., Wagner, K., Bats, J. W., Ziegler, K. & Frimmer, M. (1986). Angew. Chem. Int. Ed. Engl. 25, 997-999.]). The title compound has been shown to have immunosuppressive activity, and no toxicity at high doses (Wieczorek et al., 1991[Wieczorek, Z., Bengtsson, B., Trojnar, I. & Siemion, I. Z. (1991). Pept. Res. 4, 275-283.]; Gaymes et al., 1997[Gaymes, T. J., Cebrat, M., Siemion, I. Z. & Kay, J. E. (1997). FEBS Lett. 418, 224-227.]).

Synthesis and crystallization

The crystals were found unintentionally after the title compound was dissolved in DMSO, and allowed to evaporate slowly at ambient temperature. Single crystal X-ray diffraction data for the title compound were collected using the Canadian Macromolecular Crystallography Facility CMCF-BM beamline at the Canadian Light Source (CLS), described by Grochulski et al. (2011[Grochulski, P., Fodje, M. N., Gorin, J., Labiuk, S. L. & Berg, R. (2011). J. Synchrotron Rad. 18, 681-684.]). The CMCF-BM is a bending magnet beamline equipped with an Si (111) double-crystal monochromator, Rayonix MX300HE CCD detector and MD2 microdiffractometer equipped with Mini Kappa Goniometer Head. Data for the title compound were collected at 18.000 keV (0.68882 Å) and 100 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Cell refinement and data reduction were performed using XDS (Kabsch, 1993[Kabsch, W. (1993). J. Appl. Cryst. 26, 795-800.]). A semi-empirical absorption correction, based on the multiple measurements of equivalent reflections, and merging of data was performed using SADABS (Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.]). Data conversion from XDS file format to SADABS file format was performed using XDS2SAD (Sheldrick, 2008a[Sheldrick, G. M. (2008a). XDS2SAD University of Göttingen, Germany.]). The space group was confirmed by XPREP routines (Bruker, 2014[Bruker (2014). XPREP. Bruker AXS Inc. Madison, Wisconsin, USA.]). The structures were solved by direct-methods and refined by full-matrix least squares and difference-Fourier techniques with SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]). All non-H atoms were refined by full-matrix least squares with anisotropic displacement parameters. A final verification of possible voids was performed using the VOID routine of PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]). The checkCIF routine and structure-factor analyses were performed by PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]). All publication materials were prepared using LinXTL (Spasyuk, 2009[Spasyuk, D. M. (2009). LinXTL. University of Montreal, Canada. http://sourceforge.net/projects/linxtl/]) and Mercury (Macrae et al., 2020[Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226-235.]).

Table 2
Experimental details

Crystal data
Chemical formula C57H84N9O9·C2H6OS
Mr 1117.45
Crystal system, space group Orthorhombic, P212121
Temperature (K) 100
a, b, c (Å) 9.942 (2), 22.986 (5), 26.512 (5)
V3) 6059 (2)
Z 4
Radiation type Synchrotron, λ = 0.68882 Å
μ (mm−1) 0.11
Crystal size (mm) 0.05 × 0.01 × 0.01
 
Data collection
Diffractometer Rayonix MX300HE CCD area detector
Absorption correction Multi-scan (SADABS; Sheldrick, 1996)
Tmin, Tmax 0.415, 0.494
No. of measured, independent and observed [I > 2σ(I)] reflections 83438, 11739, 10684
Rint 0.083
(sin θ/λ)max−1) 0.614
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.101, 1.04
No. of reflections 11739
No. of parameters 726
No. of restraints 6
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.39, −0.30
Absolute structure Flack x determined using 4488 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.00 (4)
Computer programs: MxDC (Fodje, 2012[Fodje, M., Janzen, K., Berg, R., Black, G., Labiuk, S., Gorin, J. & Grochulski, P. (2012). J. Synchrotron Rad. 19, 274-280.]), XDS (Kabsch, 2010[Kabsch, W. (2010). Acta Cryst. D66, 125-132.]), SHELXS (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]), SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ShelXle (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]), LinXTL (Spasyuk, 2009[Spasyuk, D. M. (2009). LinXTL. University of Montreal, Canada. http://sourceforge.net/projects/linxtl/]) and Mercury (Macrae et al., 2020[Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226-235.]).

Structural data


Computing details top

Data collection: MxDC (Fodje, 2012); cell refinement: XDS (Kabsch, 2010); data reduction: XDS (Kabsch, 2010); program(s) used to solve structure: SHELXS (Sheldrick, 2008b); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ShelXle (Hübschle et al., 2011); software used to prepare material for publication: LinXTL (Spasyuk, 2009) and Mercury (Macrae et al., 2020).

24,27-Dibenzyl-15,18-bis(butan-2-yl)-12,21-bis(2-methylpropyl)-9-(propan-2-yl)-1,7,10,13,16,19,22,25,28-nonaazatricyclo[28.3.0.03,7]tritriacontane-2,8,11,14,17,20,23,26,29-nonone dimethyl sulfoxide monosolvate top
Crystal data top
C57H84N9O9·C2H6OSDx = 1.225 Mg m3
Mr = 1117.45Synchrotron radiation, λ = 0.68882 Å
Orthorhombic, P212121Cell parameters from 17346 reflections
a = 9.942 (2) Åθ = 1.1–30.5°
b = 22.986 (5) ŵ = 0.11 mm1
c = 26.512 (5) ÅT = 100 K
V = 6059 (2) Å3Needle, colourless
Z = 40.05 × 0.01 × 0.01 mm
F(000) = 2412
Data collection top
Rayonix MX300HE CCD area detector
diffractometer
10684 reflections with I > 2σ(I)
Radiation source: synchrotronRint = 0.083
κ and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.415, Tmax = 0.494k = 2828
83438 measured reflectionsl = 3232
11739 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0567P)2 + 1.3012P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max = 0.001
wR(F2) = 0.101Δρmax = 0.39 e Å3
S = 1.04Δρmin = 0.29 e Å3
11739 reflectionsExtinction correction: SHELXL2016 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
726 parametersExtinction coefficient: 0.0137 (8)
6 restraintsAbsolute structure: Flack x determined using 4488 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sitesAbsolute structure parameter: 0.00 (4)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The H atoms were generated geometrically (C—H 0.93 to 0.98, N—H 0.86 and O—H 0.82?Å) and were included in the refinement in the riding model approximation; their displacement parameterwere set to 1.5 times those of the equivalent isotropic temperature factors of the parent site (methyl) and 1.2 times for others.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2960 (3)0.28363 (12)0.63624 (9)0.0186 (5)
H10.3933020.2828220.6457920.022*
C20.2427 (3)0.22180 (12)0.62660 (10)0.0237 (6)
H2A0.2524390.2108910.5906590.028*
H2B0.2905730.1929080.6476900.028*
C30.0946 (3)0.22615 (13)0.64156 (10)0.0251 (6)
H3A0.0405340.2436910.6141340.030*
H3B0.0573250.1873720.6498310.030*
C40.0969 (3)0.26534 (12)0.68789 (10)0.0206 (5)
H4A0.0125610.2880290.6907200.025*
H4B0.1096750.2423530.7190970.025*
C50.2395 (3)0.35445 (12)0.70124 (9)0.0187 (5)
C60.1467 (3)0.37058 (12)0.74561 (9)0.0188 (5)
H60.0525900.3595390.7362890.023*
C70.1481 (3)0.43575 (12)0.75826 (10)0.0223 (6)
H70.2419190.4475260.7672430.027*
C80.1014 (3)0.47150 (13)0.71281 (11)0.0314 (7)
H8A0.0093800.4602730.7038210.047*
H8B0.1613040.4641480.6841590.047*
H8C0.1036140.5129660.7213630.047*
C90.0561 (3)0.44747 (14)0.80322 (10)0.0260 (6)
H9A0.0360050.4358870.7947610.039*
H9B0.0580220.4890420.8113880.039*
H9C0.0873480.4250080.8323760.039*
C100.1040 (3)0.29885 (12)0.81360 (9)0.0196 (5)
C110.1734 (3)0.25834 (12)0.85275 (9)0.0189 (5)
H110.2186670.2270670.8327700.023*
C120.0714 (3)0.22740 (12)0.88682 (10)0.0217 (6)
H12A0.1081890.2252770.9214690.026*
H12B0.0122870.2507150.8881190.026*
C130.0374 (3)0.16610 (12)0.86894 (10)0.0229 (6)
H130.0322290.1665340.8312700.027*
C140.0994 (3)0.14716 (13)0.88945 (12)0.0309 (7)
H14A0.0955340.1451960.9263420.046*
H14B0.1223570.1087580.8759000.046*
H14C0.1680820.1754000.8792490.046*
C150.1460 (4)0.12289 (15)0.88447 (13)0.0405 (8)
H15A0.2337090.1365660.8724300.061*
H15B0.1264230.0847630.8696420.061*
H15C0.1478530.1195450.9213100.061*
C160.2541 (3)0.33778 (11)0.90634 (9)0.0175 (5)
C170.3714 (3)0.36376 (11)0.93570 (9)0.0173 (5)
H170.3674200.3469280.9704490.021*
C180.3572 (3)0.42997 (11)0.94141 (10)0.0197 (5)
H180.2655420.4379520.9553220.024*
C190.3683 (3)0.46159 (12)0.89083 (11)0.0264 (6)
H19A0.4644860.4662990.8821380.032*
H19B0.3260860.4373820.8643000.032*
C200.3014 (4)0.52111 (14)0.89121 (15)0.0450 (9)
H20A0.2041730.5164470.8956600.067*
H20B0.3192190.5409210.8591610.067*
H20C0.3378420.5443240.9190460.067*
C210.4601 (3)0.45288 (12)0.97960 (10)0.0237 (6)
H21A0.4471750.4331781.0120170.036*
H21B0.4476310.4948630.9840280.036*
H21C0.5512060.4452470.9671590.036*
C220.5943 (3)0.31953 (11)0.94307 (9)0.0159 (5)
C230.7263 (3)0.30260 (11)0.91749 (9)0.0161 (5)
H230.7610080.2666140.9342160.019*
C240.8330 (3)0.35108 (11)0.92385 (9)0.0179 (5)
H240.9178340.3361210.9082760.021*
C250.8658 (3)0.36478 (12)0.97918 (10)0.0227 (6)
H25A0.9362200.3952070.9800960.027*
H25B0.7843290.3810110.9953990.027*
C260.9137 (3)0.31302 (14)1.00990 (11)0.0308 (7)
H26A0.8395590.2853031.0140030.046*
H26B0.9438180.3263451.0431380.046*
H26C0.9884940.2939970.9923800.046*
C270.7970 (3)0.40725 (12)0.89575 (10)0.0219 (6)
H27A0.7194290.4256570.9120330.033*
H27B0.7747330.3980840.8606320.033*
H27C0.8738920.4339150.8966300.033*
C280.6247 (3)0.25351 (11)0.84263 (9)0.0156 (5)
C290.6293 (3)0.24907 (11)0.78470 (9)0.0166 (5)
H290.5374320.2379600.7727170.020*
C300.7264 (3)0.20104 (11)0.76897 (9)0.0188 (5)
H30A0.6971600.1642770.7850290.023*
H30B0.8165880.2105730.7824830.023*
C310.7395 (3)0.19054 (12)0.71180 (10)0.0210 (6)
H310.7847090.2251320.6964440.025*
C320.8294 (3)0.13762 (13)0.70376 (11)0.0291 (7)
H32A0.9172240.1445330.7194720.044*
H32B0.8414720.1309520.6675290.044*
H32C0.7874440.1033490.7191080.044*
C330.6040 (3)0.18198 (14)0.68568 (11)0.0299 (7)
H33A0.6185020.1753610.6495660.045*
H33B0.5485820.2168230.6903580.045*
H33C0.5580230.1482810.7003400.045*
C340.5851 (3)0.35148 (11)0.76922 (9)0.0153 (5)
C350.6307 (3)0.40770 (11)0.74322 (9)0.0157 (5)
H350.7236930.4165260.7553470.019*
C360.5415 (3)0.45916 (11)0.75762 (10)0.0192 (5)
H36A0.4611460.4591140.7355530.023*
H36B0.5101840.4537250.7927530.023*
C370.6096 (3)0.51789 (11)0.75357 (9)0.0186 (5)
C380.7203 (3)0.53083 (12)0.78370 (11)0.0256 (6)
H380.7541960.5023970.8063830.031*
C390.7816 (3)0.58518 (14)0.78079 (13)0.0337 (7)
H390.8576980.5935630.8012110.040*
C400.7316 (4)0.62720 (14)0.74804 (12)0.0350 (8)
H400.7735000.6642840.7460130.042*
C410.6213 (4)0.61485 (13)0.71858 (11)0.0325 (7)
H410.5865840.6434790.6962510.039*
C420.5607 (3)0.56058 (12)0.72150 (11)0.0244 (6)
H420.4843650.5525150.7011330.029*
C430.7495 (3)0.37703 (11)0.66673 (9)0.0171 (5)
C440.7523 (3)0.37092 (11)0.60924 (10)0.0176 (5)
H440.8213660.3407370.6010480.021*
C450.7996 (3)0.42808 (12)0.58501 (10)0.0218 (6)
H45A0.7326580.4589190.5920220.026*
H45B0.8859020.4399870.6005380.026*
C460.8183 (3)0.42259 (11)0.52855 (10)0.0205 (6)
C470.7286 (3)0.44815 (12)0.49512 (11)0.0258 (6)
H470.6541320.4695970.5076720.031*
C480.7473 (3)0.44256 (14)0.44313 (11)0.0304 (7)
H480.6849510.4599840.4205500.036*
C490.8557 (4)0.41183 (13)0.42429 (10)0.0299 (7)
H490.8687520.4085690.3889070.036*
C500.9456 (3)0.38574 (12)0.45745 (11)0.0264 (6)
H501.0197830.3642290.4446970.032*
C510.9273 (3)0.39105 (12)0.50941 (10)0.0215 (6)
H510.9891080.3731590.5319080.026*
C520.6105 (3)0.29527 (11)0.57304 (9)0.0189 (5)
C530.4766 (3)0.27766 (11)0.54925 (10)0.0194 (5)
H530.4461350.2400400.5643450.023*
C540.4909 (3)0.27020 (13)0.49163 (10)0.0260 (6)
H54A0.5837100.2588240.4823630.031*
H54B0.4273860.2405710.4786950.031*
C550.4568 (3)0.33019 (13)0.47142 (10)0.0269 (6)
H55A0.4294800.3282070.4355570.032*
H55B0.5345190.3568760.4746360.032*
C560.3405 (3)0.34999 (13)0.50447 (9)0.0246 (6)
H56A0.3403780.3928090.5085300.029*
H56B0.2530800.3375720.4901960.029*
C570.2729 (3)0.32246 (12)0.59002 (9)0.0186 (5)
N10.2127 (2)0.30369 (10)0.67852 (8)0.0182 (5)
N20.1890 (2)0.33375 (10)0.78791 (8)0.0195 (5)
H2N0.2740790.3344400.7969990.023*
N30.2804 (2)0.28902 (9)0.87956 (8)0.0175 (4)
H3N0.3631790.2755630.8782570.021*
N40.5000 (2)0.34647 (9)0.91426 (8)0.0156 (4)
H4N0.5169720.3535520.8822650.019*
N50.7134 (2)0.29074 (9)0.86333 (8)0.0162 (4)
H5N0.7678760.3094180.8427830.019*
N60.6638 (2)0.30463 (10)0.76177 (8)0.0172 (4)
H6N0.7363520.3075910.7429530.021*
N70.6377 (2)0.39981 (9)0.68821 (8)0.0171 (4)
N80.6252 (2)0.35076 (9)0.58825 (8)0.0177 (4)
H8N0.5572780.3751220.5854890.021*
N90.3678 (2)0.32044 (10)0.55315 (8)0.0191 (5)
O10.17144 (19)0.35242 (9)0.58599 (7)0.0232 (4)
O20.33654 (19)0.38488 (9)0.68831 (7)0.0238 (4)
O30.01718 (19)0.29596 (9)0.80507 (7)0.0246 (4)
O40.14142 (19)0.35982 (8)0.90759 (7)0.0224 (4)
O50.58021 (19)0.31123 (9)0.98829 (6)0.0217 (4)
O60.5431 (2)0.22437 (8)0.86719 (7)0.0200 (4)
O70.48473 (18)0.34897 (8)0.79686 (6)0.0186 (4)
O80.84805 (19)0.36238 (9)0.69175 (7)0.0248 (4)
O90.6992 (2)0.25795 (9)0.57647 (8)0.0298 (5)
O1S0.4825 (2)0.45567 (10)0.59265 (12)0.0515 (7)
S1S0.38431 (7)0.49945 (3)0.61123 (3)0.02677 (17)
C1S0.2354 (4)0.48972 (14)0.57543 (12)0.0349 (7)
H1S10.2561380.4936170.5394530.052*
H1S20.1691470.5192670.5851140.052*
H1S30.1984480.4509070.5819310.052*
C2S0.4379 (4)0.56766 (14)0.58597 (14)0.0403 (8)
H2S10.5290010.5763310.5978720.060*
H2S20.3763370.5983860.5971280.060*
H2S30.4376200.5656970.5490420.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0184 (13)0.0231 (13)0.0142 (11)0.0022 (11)0.0009 (10)0.0006 (10)
C20.0310 (16)0.0221 (14)0.0181 (12)0.0020 (12)0.0031 (11)0.0027 (11)
C30.0286 (16)0.0250 (14)0.0219 (13)0.0061 (12)0.0020 (12)0.0029 (11)
C40.0185 (14)0.0220 (13)0.0212 (12)0.0029 (11)0.0024 (11)0.0016 (10)
C50.0129 (12)0.0299 (14)0.0132 (11)0.0023 (11)0.0023 (10)0.0002 (11)
C60.0155 (13)0.0275 (14)0.0133 (11)0.0014 (11)0.0003 (10)0.0025 (10)
C70.0171 (14)0.0298 (15)0.0202 (12)0.0018 (11)0.0007 (11)0.0036 (11)
C80.0385 (18)0.0297 (15)0.0259 (14)0.0008 (14)0.0057 (13)0.0006 (12)
C90.0235 (15)0.0359 (16)0.0187 (13)0.0032 (12)0.0014 (11)0.0049 (12)
C100.0186 (14)0.0261 (13)0.0141 (11)0.0031 (11)0.0035 (10)0.0059 (10)
C110.0173 (14)0.0218 (13)0.0175 (12)0.0058 (10)0.0011 (10)0.0058 (10)
C120.0189 (14)0.0261 (14)0.0201 (12)0.0060 (11)0.0037 (11)0.0013 (11)
C130.0291 (16)0.0198 (13)0.0199 (13)0.0041 (12)0.0009 (11)0.0025 (11)
C140.0320 (17)0.0263 (15)0.0345 (15)0.0097 (13)0.0002 (13)0.0065 (13)
C150.047 (2)0.0341 (17)0.0405 (18)0.0166 (16)0.0101 (16)0.0112 (15)
C160.0151 (13)0.0232 (13)0.0142 (11)0.0033 (11)0.0024 (10)0.0016 (10)
C170.0156 (13)0.0233 (13)0.0131 (11)0.0002 (10)0.0027 (10)0.0004 (10)
C180.0176 (13)0.0227 (13)0.0190 (12)0.0001 (11)0.0019 (10)0.0040 (11)
C190.0285 (16)0.0235 (14)0.0272 (14)0.0029 (12)0.0065 (12)0.0028 (12)
C200.052 (2)0.0257 (16)0.057 (2)0.0045 (15)0.0255 (19)0.0011 (16)
C210.0241 (15)0.0276 (14)0.0194 (13)0.0033 (12)0.0015 (11)0.0063 (11)
C220.0162 (13)0.0160 (12)0.0153 (11)0.0039 (10)0.0012 (10)0.0006 (9)
C230.0164 (13)0.0192 (12)0.0128 (11)0.0005 (10)0.0004 (10)0.0010 (10)
C240.0145 (13)0.0204 (13)0.0188 (12)0.0013 (10)0.0002 (10)0.0010 (10)
C250.0214 (14)0.0253 (14)0.0214 (13)0.0004 (11)0.0034 (11)0.0036 (11)
C260.0331 (17)0.0364 (17)0.0228 (13)0.0029 (13)0.0104 (12)0.0004 (12)
C270.0201 (14)0.0217 (13)0.0239 (13)0.0022 (11)0.0016 (11)0.0015 (11)
C280.0151 (13)0.0150 (11)0.0165 (11)0.0001 (10)0.0023 (10)0.0000 (10)
C290.0172 (13)0.0177 (12)0.0149 (11)0.0008 (10)0.0008 (10)0.0000 (10)
C300.0209 (14)0.0181 (13)0.0172 (12)0.0014 (11)0.0007 (10)0.0015 (10)
C310.0252 (15)0.0212 (13)0.0164 (12)0.0027 (11)0.0028 (11)0.0032 (10)
C320.0321 (17)0.0267 (15)0.0286 (14)0.0006 (13)0.0070 (12)0.0077 (12)
C330.0315 (17)0.0390 (17)0.0192 (13)0.0021 (14)0.0030 (12)0.0053 (12)
C340.0139 (12)0.0215 (13)0.0105 (10)0.0011 (10)0.0022 (9)0.0016 (9)
C350.0141 (13)0.0186 (12)0.0144 (11)0.0014 (10)0.0001 (10)0.0012 (10)
C360.0190 (13)0.0175 (13)0.0212 (13)0.0006 (10)0.0022 (11)0.0016 (10)
C370.0201 (13)0.0191 (12)0.0167 (12)0.0007 (10)0.0039 (10)0.0032 (10)
C380.0262 (15)0.0241 (14)0.0265 (14)0.0035 (12)0.0027 (12)0.0018 (12)
C390.0321 (18)0.0314 (16)0.0376 (17)0.0091 (13)0.0005 (14)0.0080 (14)
C400.044 (2)0.0220 (15)0.0387 (17)0.0102 (14)0.0149 (15)0.0047 (13)
C410.0455 (19)0.0232 (14)0.0289 (15)0.0042 (14)0.0113 (14)0.0031 (12)
C420.0266 (15)0.0235 (14)0.0231 (13)0.0025 (12)0.0026 (11)0.0001 (11)
C430.0159 (13)0.0173 (12)0.0182 (12)0.0008 (10)0.0003 (10)0.0016 (10)
C440.0135 (12)0.0208 (12)0.0185 (12)0.0015 (10)0.0002 (10)0.0005 (10)
C450.0212 (14)0.0240 (14)0.0203 (12)0.0029 (11)0.0018 (11)0.0009 (11)
C460.0230 (15)0.0194 (13)0.0192 (12)0.0056 (11)0.0003 (11)0.0034 (10)
C470.0240 (15)0.0257 (14)0.0277 (14)0.0023 (12)0.0025 (12)0.0066 (12)
C480.0351 (17)0.0323 (16)0.0236 (14)0.0093 (14)0.0097 (13)0.0092 (12)
C490.049 (2)0.0266 (15)0.0142 (12)0.0116 (14)0.0001 (13)0.0025 (11)
C500.0329 (17)0.0210 (14)0.0254 (14)0.0064 (12)0.0051 (12)0.0025 (11)
C510.0228 (14)0.0202 (13)0.0216 (13)0.0023 (11)0.0004 (11)0.0018 (10)
C520.0211 (14)0.0222 (13)0.0134 (11)0.0001 (11)0.0037 (10)0.0012 (10)
C530.0231 (15)0.0168 (12)0.0184 (12)0.0020 (11)0.0017 (10)0.0025 (10)
C540.0302 (16)0.0296 (15)0.0181 (13)0.0024 (12)0.0021 (11)0.0073 (11)
C550.0319 (16)0.0339 (16)0.0149 (12)0.0011 (13)0.0033 (11)0.0010 (11)
C560.0342 (16)0.0256 (14)0.0139 (12)0.0032 (12)0.0016 (11)0.0019 (11)
C570.0193 (14)0.0231 (13)0.0132 (11)0.0011 (11)0.0013 (10)0.0038 (10)
N10.0157 (11)0.0247 (11)0.0142 (10)0.0012 (9)0.0018 (8)0.0009 (9)
N20.0129 (11)0.0337 (13)0.0120 (10)0.0049 (9)0.0003 (8)0.0004 (9)
N30.0138 (11)0.0208 (11)0.0177 (10)0.0011 (9)0.0007 (8)0.0021 (9)
N40.0150 (11)0.0202 (11)0.0115 (9)0.0010 (9)0.0026 (8)0.0010 (8)
N50.0152 (11)0.0202 (11)0.0133 (10)0.0027 (9)0.0003 (8)0.0005 (8)
N60.0169 (11)0.0196 (11)0.0150 (10)0.0003 (9)0.0036 (8)0.0012 (9)
N70.0166 (11)0.0200 (11)0.0148 (10)0.0028 (9)0.0018 (8)0.0008 (8)
N80.0169 (11)0.0205 (11)0.0159 (10)0.0011 (9)0.0009 (8)0.0007 (9)
N90.0209 (12)0.0217 (11)0.0147 (10)0.0031 (9)0.0011 (9)0.0008 (9)
O10.0200 (10)0.0300 (10)0.0196 (9)0.0059 (8)0.0007 (8)0.0016 (8)
O20.0180 (10)0.0328 (11)0.0206 (9)0.0071 (8)0.0035 (8)0.0056 (8)
O30.0150 (10)0.0387 (11)0.0202 (9)0.0064 (8)0.0000 (7)0.0022 (8)
O40.0149 (10)0.0278 (10)0.0245 (9)0.0009 (8)0.0010 (7)0.0054 (8)
O50.0213 (10)0.0316 (10)0.0123 (8)0.0013 (8)0.0016 (7)0.0030 (7)
O60.0219 (10)0.0198 (9)0.0185 (9)0.0042 (8)0.0014 (7)0.0007 (8)
O70.0146 (9)0.0233 (9)0.0180 (9)0.0010 (7)0.0029 (7)0.0017 (7)
O80.0159 (10)0.0387 (11)0.0199 (9)0.0038 (8)0.0009 (8)0.0013 (8)
O90.0274 (12)0.0242 (10)0.0379 (11)0.0059 (9)0.0018 (9)0.0037 (9)
O1S0.0295 (13)0.0225 (11)0.102 (2)0.0109 (10)0.0132 (14)0.0067 (13)
S1S0.0244 (4)0.0258 (3)0.0301 (4)0.0021 (3)0.0009 (3)0.0077 (3)
C1S0.0402 (19)0.0315 (16)0.0331 (16)0.0116 (14)0.0101 (14)0.0058 (13)
C2S0.044 (2)0.0269 (16)0.050 (2)0.0049 (15)0.0154 (17)0.0083 (15)
Geometric parameters (Å, º) top
C1—N11.468 (3)C29—C301.525 (4)
C1—C571.533 (4)C29—H291.0000
C1—C21.538 (4)C30—C311.540 (3)
C1—H11.0000C30—H30A0.9900
C2—C31.528 (4)C30—H30B0.9900
C2—H2A0.9900C31—C321.525 (4)
C2—H2B0.9900C31—C331.528 (4)
C3—C41.523 (4)C31—H311.0000
C3—H3A0.9900C32—H32A0.9800
C3—H3B0.9900C32—H32B0.9800
C4—N11.472 (3)C32—H32C0.9800
C4—H4A0.9900C33—H33A0.9800
C4—H4B0.9900C33—H33B0.9800
C5—O21.240 (3)C33—H33C0.9800
C5—N11.340 (3)C34—O71.239 (3)
C5—C61.540 (3)C34—N61.345 (3)
C6—N21.467 (3)C34—C351.533 (4)
C6—C71.535 (4)C35—N71.471 (3)
C6—H61.0000C35—C361.527 (4)
C7—C91.526 (4)C35—H351.0000
C7—C81.531 (4)C36—C371.514 (4)
C7—H71.0000C36—H36A0.9900
C8—H8A0.9800C36—H36B0.9900
C8—H8B0.9800C37—C421.386 (4)
C8—H8C0.9800C37—C381.392 (4)
C9—H9A0.9800C38—C391.392 (4)
C9—H9B0.9800C38—H380.9500
C9—H9C0.9800C39—C401.391 (5)
C10—O31.228 (3)C39—H390.9500
C10—N21.349 (3)C40—C411.376 (5)
C10—C111.556 (4)C40—H400.9500
C11—N31.461 (3)C41—C421.387 (4)
C11—C121.533 (4)C41—H410.9500
C11—H111.0000C42—H420.9500
C12—C131.525 (4)C43—O81.230 (3)
C12—H12A0.9900C43—N71.355 (3)
C12—H12B0.9900C43—C441.531 (4)
C13—C151.524 (4)C44—N81.457 (3)
C13—C141.528 (4)C44—C451.536 (4)
C13—H131.0000C44—H441.0000
C14—H14A0.9800C45—C461.514 (4)
C14—H14B0.9800C45—H45A0.9900
C14—H14C0.9800C45—H45B0.9900
C15—H15A0.9800C46—C471.388 (4)
C15—H15B0.9800C46—C511.399 (4)
C15—H15C0.9800C47—C481.397 (4)
C16—O41.230 (3)C47—H470.9500
C16—N31.352 (3)C48—C491.383 (5)
C16—C171.524 (4)C48—H480.9500
C17—N41.455 (3)C49—C501.390 (5)
C17—C181.536 (4)C49—H490.9500
C17—H171.0000C50—C511.395 (4)
C18—C191.529 (4)C50—H500.9500
C18—C211.532 (4)C51—H510.9500
C18—H181.0000C52—O91.234 (3)
C19—C201.521 (4)C52—N81.346 (3)
C19—H19A0.9900C52—C531.527 (4)
C19—H19B0.9900C53—N91.466 (3)
C20—H20A0.9800C53—C541.544 (4)
C20—H20B0.9800C53—H531.0000
C20—H20C0.9800C54—C551.518 (4)
C21—H21A0.9800C54—H54A0.9900
C21—H21B0.9800C54—H54B0.9900
C21—H21C0.9800C55—C561.521 (4)
C22—O51.222 (3)C55—H55A0.9900
C22—N41.358 (3)C55—H55B0.9900
C22—C231.528 (4)C56—N91.483 (3)
C23—N51.467 (3)C56—H56A0.9900
C23—C241.548 (4)C56—H56B0.9900
C23—H231.0000C57—O11.226 (3)
C24—C271.533 (4)C57—N91.359 (3)
C24—C251.535 (4)N2—H2N0.8800
C24—H241.0000N3—H3N0.8800
C25—C261.518 (4)N4—H4N0.8800
C25—H25A0.9900N5—H5N0.8800
C25—H25B0.9900N6—H6N0.8800
C26—H26A0.9800N8—H8N0.8800
C26—H26B0.9800O1S—S1S1.486 (2)
C26—H26C0.9800S1S—C1S1.773 (3)
C27—H27A0.9800S1S—C2S1.786 (3)
C27—H27B0.9800C1S—H1S10.9800
C27—H27C0.9800C1S—H1S20.9800
C28—O61.237 (3)C1S—H1S30.9800
C28—N51.346 (3)C2S—H2S10.9800
C28—C291.540 (3)C2S—H2S20.9800
C29—N61.455 (3)C2S—H2S30.9800
N1—C1—C57110.1 (2)C29—C30—H30A108.3
N1—C1—C2102.9 (2)C31—C30—H30A108.3
C57—C1—C2110.7 (2)C29—C30—H30B108.3
N1—C1—H1111.0C31—C30—H30B108.3
C57—C1—H1111.0H30A—C30—H30B107.4
C2—C1—H1111.0C32—C31—C33110.6 (2)
C3—C2—C1103.2 (2)C32—C31—C30108.2 (2)
C3—C2—H2A111.1C33—C31—C30113.1 (2)
C1—C2—H2A111.1C32—C31—H31108.3
C3—C2—H2B111.1C33—C31—H31108.3
C1—C2—H2B111.1C30—C31—H31108.3
H2A—C2—H2B109.1C31—C32—H32A109.5
C4—C3—C2103.5 (2)C31—C32—H32B109.5
C4—C3—H3A111.1H32A—C32—H32B109.5
C2—C3—H3A111.1C31—C32—H32C109.5
C4—C3—H3B111.1H32A—C32—H32C109.5
C2—C3—H3B111.1H32B—C32—H32C109.5
H3A—C3—H3B109.0C31—C33—H33A109.5
N1—C4—C3103.3 (2)C31—C33—H33B109.5
N1—C4—H4A111.1H33A—C33—H33B109.5
C3—C4—H4A111.1C31—C33—H33C109.5
N1—C4—H4B111.1H33A—C33—H33C109.5
C3—C4—H4B111.1H33B—C33—H33C109.5
H4A—C4—H4B109.1O7—C34—N6121.2 (2)
O2—C5—N1121.4 (2)O7—C34—C35122.9 (2)
O2—C5—C6122.8 (2)N6—C34—C35115.9 (2)
N1—C5—C6115.7 (2)N7—C35—C36111.8 (2)
N2—C6—C7113.2 (2)N7—C35—C34110.8 (2)
N2—C6—C5105.9 (2)C36—C35—C34111.7 (2)
C7—C6—C5113.3 (2)N7—C35—H35107.4
N2—C6—H6108.1C36—C35—H35107.4
C7—C6—H6108.1C34—C35—H35107.4
C5—C6—H6108.1C37—C36—C35114.4 (2)
C9—C7—C8109.8 (2)C37—C36—H36A108.7
C9—C7—C6109.7 (2)C35—C36—H36A108.7
C8—C7—C6110.4 (2)C37—C36—H36B108.7
C9—C7—H7109.0C35—C36—H36B108.7
C8—C7—H7109.0H36A—C36—H36B107.6
C6—C7—H7109.0C42—C37—C38118.5 (3)
C7—C8—H8A109.5C42—C37—C36121.2 (2)
C7—C8—H8B109.5C38—C37—C36120.2 (2)
H8A—C8—H8B109.5C37—C38—C39120.4 (3)
C7—C8—H8C109.5C37—C38—H38119.8
H8A—C8—H8C109.5C39—C38—H38119.8
H8B—C8—H8C109.5C40—C39—C38120.1 (3)
C7—C9—H9A109.5C40—C39—H39120.0
C7—C9—H9B109.5C38—C39—H39120.0
H9A—C9—H9B109.5C41—C40—C39119.7 (3)
C7—C9—H9C109.5C41—C40—H40120.1
H9A—C9—H9C109.5C39—C40—H40120.1
H9B—C9—H9C109.5C40—C41—C42120.0 (3)
O3—C10—N2123.6 (3)C40—C41—H41120.0
O3—C10—C11121.7 (2)C42—C41—H41120.0
N2—C10—C11114.5 (2)C37—C42—C41121.3 (3)
N3—C11—C12114.8 (2)C37—C42—H42119.4
N3—C11—C10111.0 (2)C41—C42—H42119.4
C12—C11—C10112.2 (2)O8—C43—N7122.2 (2)
N3—C11—H11106.1O8—C43—C44119.8 (2)
C12—C11—H11106.1N7—C43—C44118.0 (2)
C10—C11—H11106.1N8—C44—C43113.2 (2)
C13—C12—C11113.1 (2)N8—C44—C45112.2 (2)
C13—C12—H12A109.0C43—C44—C45110.1 (2)
C11—C12—H12A109.0N8—C44—H44107.0
C13—C12—H12B109.0C43—C44—H44107.0
C11—C12—H12B109.0C45—C44—H44107.0
H12A—C12—H12B107.8C46—C45—C44112.3 (2)
C15—C13—C12111.2 (3)C46—C45—H45A109.1
C15—C13—C14110.4 (2)C44—C45—H45A109.1
C12—C13—C14110.5 (2)C46—C45—H45B109.1
C15—C13—H13108.2C44—C45—H45B109.1
C12—C13—H13108.2H45A—C45—H45B107.9
C14—C13—H13108.2C47—C46—C51119.0 (3)
C13—C14—H14A109.5C47—C46—C45121.2 (3)
C13—C14—H14B109.5C51—C46—C45119.8 (2)
H14A—C14—H14B109.5C46—C47—C48120.4 (3)
C13—C14—H14C109.5C46—C47—H47119.8
H14A—C14—H14C109.5C48—C47—H47119.8
H14B—C14—H14C109.5C49—C48—C47120.5 (3)
C13—C15—H15A109.5C49—C48—H48119.8
C13—C15—H15B109.5C47—C48—H48119.8
H15A—C15—H15B109.5C48—C49—C50119.6 (3)
C13—C15—H15C109.5C48—C49—H49120.2
H15A—C15—H15C109.5C50—C49—H49120.2
H15B—C15—H15C109.5C49—C50—C51120.2 (3)
O4—C16—N3122.1 (2)C49—C50—H50119.9
O4—C16—C17121.5 (2)C51—C50—H50119.9
N3—C16—C17116.4 (2)C50—C51—C46120.3 (3)
N4—C17—C16111.5 (2)C50—C51—H51119.8
N4—C17—C18112.9 (2)C46—C51—H51119.8
C16—C17—C18111.6 (2)O9—C52—N8124.0 (3)
N4—C17—H17106.8O9—C52—C53118.0 (2)
C16—C17—H17106.8N8—C52—C53118.0 (2)
C18—C17—H17106.8N9—C53—C52115.9 (2)
C19—C18—C21111.6 (2)N9—C53—C54102.3 (2)
C19—C18—C17112.2 (2)C52—C53—C54111.0 (2)
C21—C18—C17110.1 (2)N9—C53—H53109.1
C19—C18—H18107.6C52—C53—H53109.1
C21—C18—H18107.6C54—C53—H53109.1
C17—C18—H18107.6C55—C54—C53103.2 (2)
C20—C19—C18113.0 (3)C55—C54—H54A111.1
C20—C19—H19A109.0C53—C54—H54A111.1
C18—C19—H19A109.0C55—C54—H54B111.1
C20—C19—H19B109.0C53—C54—H54B111.1
C18—C19—H19B109.0H54A—C54—H54B109.1
H19A—C19—H19B107.8C54—C55—C56103.8 (2)
C19—C20—H20A109.5C54—C55—H55A111.0
C19—C20—H20B109.5C56—C55—H55A111.0
H20A—C20—H20B109.5C54—C55—H55B111.0
C19—C20—H20C109.5C56—C55—H55B111.0
H20A—C20—H20C109.5H55A—C55—H55B109.0
H20B—C20—H20C109.5N9—C56—C55103.0 (2)
C18—C21—H21A109.5N9—C56—H56A111.2
C18—C21—H21B109.5C55—C56—H56A111.2
H21A—C21—H21B109.5N9—C56—H56B111.2
C18—C21—H21C109.5C55—C56—H56B111.2
H21A—C21—H21C109.5H56A—C56—H56B109.1
H21B—C21—H21C109.5O1—C57—N9121.8 (2)
O5—C22—N4123.0 (2)O1—C57—C1121.3 (2)
O5—C22—C23119.6 (2)N9—C57—C1116.8 (2)
N4—C22—C23117.3 (2)C5—N1—C1120.3 (2)
N5—C23—C22114.0 (2)C5—N1—C4126.9 (2)
N5—C23—C24107.5 (2)C1—N1—C4112.5 (2)
C22—C23—C24110.9 (2)C10—N2—C6123.3 (2)
N5—C23—H23108.1C10—N2—H2N118.3
C22—C23—H23108.1C6—N2—H2N118.3
C24—C23—H23108.1C16—N3—C11121.0 (2)
C27—C24—C25109.9 (2)C16—N3—H3N119.5
C27—C24—C23113.2 (2)C11—N3—H3N119.5
C25—C24—C23113.4 (2)C22—N4—C17120.7 (2)
C27—C24—H24106.6C22—N4—H4N119.6
C25—C24—H24106.6C17—N4—H4N119.6
C23—C24—H24106.6C28—N5—C23125.1 (2)
C26—C25—C24114.7 (2)C28—N5—H5N117.5
C26—C25—H25A108.6C23—N5—H5N117.5
C24—C25—H25A108.6C34—N6—C29120.3 (2)
C26—C25—H25B108.6C34—N6—H6N119.9
C24—C25—H25B108.6C29—N6—H6N119.9
H25A—C25—H25B107.6C43—N7—C35120.2 (2)
C25—C26—H26A109.5C52—N8—C44120.7 (2)
C25—C26—H26B109.5C52—N8—H8N119.7
H26A—C26—H26B109.5C44—N8—H8N119.7
C25—C26—H26C109.5C57—N9—C53125.9 (2)
H26A—C26—H26C109.5C57—N9—C56118.9 (2)
H26B—C26—H26C109.5C53—N9—C56112.4 (2)
C24—C27—H27A109.5O1S—S1S—C1S106.62 (16)
C24—C27—H27B109.5O1S—S1S—C2S105.92 (15)
H27A—C27—H27B109.5C1S—S1S—C2S99.15 (18)
C24—C27—H27C109.5S1S—C1S—H1S1109.5
H27A—C27—H27C109.5S1S—C1S—H1S2109.5
H27B—C27—H27C109.5H1S1—C1S—H1S2109.5
O6—C28—N5124.0 (2)S1S—C1S—H1S3109.5
O6—C28—C29120.6 (2)H1S1—C1S—H1S3109.5
N5—C28—C29115.4 (2)H1S2—C1S—H1S3109.5
N6—C29—C30111.8 (2)S1S—C2S—H2S1109.5
N6—C29—C28111.4 (2)S1S—C2S—H2S2109.5
C30—C29—C28109.9 (2)H2S1—C2S—H2S2109.5
N6—C29—H29107.8S1S—C2S—H2S3109.5
C30—C29—H29107.8H2S1—C2S—H2S3109.5
C28—C29—H29107.8H2S2—C2S—H2S3109.5
C29—C30—C31115.9 (2)
N1—C1—C2—C331.1 (3)C44—C45—C46—C47107.3 (3)
C57—C1—C2—C386.5 (3)C44—C45—C46—C5172.4 (3)
C1—C2—C3—C438.7 (3)C51—C46—C47—C480.2 (4)
C2—C3—C4—N130.8 (3)C45—C46—C47—C48179.9 (3)
O2—C5—C6—N2101.8 (3)C46—C47—C48—C490.5 (4)
N1—C5—C6—N275.2 (3)C47—C48—C49—C500.9 (4)
O2—C5—C6—C722.8 (4)C48—C49—C50—C510.7 (4)
N1—C5—C6—C7160.2 (2)C49—C50—C51—C460.1 (4)
N2—C6—C7—C958.2 (3)C47—C46—C51—C500.3 (4)
C5—C6—C7—C9178.7 (2)C45—C46—C51—C50179.9 (3)
N2—C6—C7—C8179.3 (2)O9—C52—C53—N9170.8 (2)
C5—C6—C7—C860.1 (3)N8—C52—C53—N910.3 (3)
O3—C10—C11—N3143.9 (2)O9—C52—C53—C5473.2 (3)
N2—C10—C11—N340.5 (3)N8—C52—C53—C54105.7 (3)
O3—C10—C11—C1214.1 (3)N9—C53—C54—C5533.0 (3)
N2—C10—C11—C12170.4 (2)C52—C53—C54—C5591.1 (3)
N3—C11—C12—C13135.4 (2)C53—C54—C55—C5639.7 (3)
C10—C11—C12—C1396.7 (3)C54—C55—C56—N930.2 (3)
C11—C12—C13—C1580.0 (3)N1—C1—C57—O120.4 (3)
C11—C12—C13—C14157.0 (2)C2—C1—C57—O192.7 (3)
O4—C16—C17—N4157.3 (2)N1—C1—C57—N9161.9 (2)
N3—C16—C17—N423.5 (3)C2—C1—C57—N985.1 (3)
O4—C16—C17—C1830.0 (3)O2—C5—N1—C12.1 (4)
N3—C16—C17—C18150.8 (2)C6—C5—N1—C1179.2 (2)
N4—C17—C18—C1960.2 (3)O2—C5—N1—C4175.9 (2)
C16—C17—C18—C1966.3 (3)C6—C5—N1—C47.0 (4)
N4—C17—C18—C2164.7 (3)C57—C1—N1—C568.9 (3)
C16—C17—C18—C21168.7 (2)C2—C1—N1—C5173.1 (2)
C21—C18—C19—C2078.8 (3)C57—C1—N1—C4105.7 (2)
C17—C18—C19—C20157.0 (3)C2—C1—N1—C412.3 (3)
O5—C22—C23—N5155.1 (2)C3—C4—N1—C5162.6 (2)
N4—C22—C23—N528.6 (3)C3—C4—N1—C111.6 (3)
O5—C22—C23—C2483.5 (3)O3—C10—N2—C62.3 (4)
N4—C22—C23—C2492.9 (3)C11—C10—N2—C6173.1 (2)
N5—C23—C24—C2758.5 (3)C7—C6—N2—C10109.7 (3)
C22—C23—C24—C2766.7 (3)C5—C6—N2—C10125.5 (3)
N5—C23—C24—C25175.3 (2)O4—C16—N3—C113.3 (4)
C22—C23—C24—C2559.4 (3)C17—C16—N3—C11175.9 (2)
C27—C24—C25—C26175.4 (2)C12—C11—N3—C1669.8 (3)
C23—C24—C25—C2656.7 (3)C10—C11—N3—C1658.7 (3)
O6—C28—C29—N6145.9 (2)O5—C22—N4—C174.1 (4)
N5—C28—C29—N633.8 (3)C23—C22—N4—C17179.7 (2)
O6—C28—C29—C3089.6 (3)C16—C17—N4—C22124.2 (2)
N5—C28—C29—C3090.7 (3)C18—C17—N4—C22109.2 (3)
N6—C29—C30—C3156.9 (3)O6—C28—N5—C230.4 (4)
C28—C29—C30—C31178.8 (2)C29—C28—N5—C23179.3 (2)
C29—C30—C31—C32174.6 (2)C22—C23—N5—C2852.7 (3)
C29—C30—C31—C3351.8 (3)C24—C23—N5—C28176.0 (2)
O7—C34—C35—N7122.8 (2)O7—C34—N6—C292.4 (4)
N6—C34—C35—N759.4 (3)C35—C34—N6—C29179.9 (2)
O7—C34—C35—C362.5 (3)C30—C29—N6—C34176.5 (2)
N6—C34—C35—C36175.2 (2)C28—C29—N6—C3460.1 (3)
N7—C35—C36—C3780.8 (3)O8—C43—N7—C350.1 (4)
C34—C35—C36—C37154.4 (2)C44—C43—N7—C35178.8 (2)
C35—C36—C37—C42119.6 (3)C36—C35—N7—C43149.9 (2)
C35—C36—C37—C3862.9 (3)C34—C35—N7—C4384.8 (3)
C42—C37—C38—C391.2 (4)O9—C52—N8—C441.5 (4)
C36—C37—C38—C39178.8 (3)C53—C52—N8—C44177.3 (2)
C37—C38—C39—C400.7 (5)C43—C44—N8—C52103.3 (3)
C38—C39—C40—C410.1 (5)C45—C44—N8—C52131.3 (2)
C39—C40—C41—C420.3 (5)O1—C57—N9—C53166.3 (2)
C38—C37—C42—C411.0 (4)C1—C57—N9—C5311.4 (4)
C36—C37—C42—C41178.6 (3)O1—C57—N9—C567.0 (4)
C40—C41—C42—C370.3 (4)C1—C57—N9—C56170.8 (2)
O8—C43—C44—N8140.3 (2)C52—C53—N9—C5793.4 (3)
N7—C43—C44—N840.9 (3)C54—C53—N9—C57145.8 (3)
O8—C43—C44—C4593.2 (3)C52—C53—N9—C56106.1 (3)
N7—C43—C44—C4585.6 (3)C54—C53—N9—C5614.7 (3)
N8—C44—C45—C4659.0 (3)C55—C56—N9—C57171.5 (2)
C43—C44—C45—C46174.0 (2)C55—C56—N9—C539.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···O70.882.122.970 (3)162
N3—H3N···O60.882.163.023 (3)166
N4—H4N···O70.882.293.117 (3)157
N5—H5N···O3i0.882.383.094 (3)139
N6—H6N···O80.882.162.926 (3)145
N8—H8N···O1S0.882.052.800 (3)150
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

The authors wish to thank F. Nelson and J. Shen for assistance with the manuscript preparation. The measurements described in this article were performed using the Canadian Macromolecular Crystallography Facility (CMCF-BM) beamline at the Canadian Light Source, a national research facility of the University of Saskatchewan, which is supported by the Canada Foundation for Innovation (CFI), the Natural Sciences and Engineering Research Council (NSERC), the National Research Council (NRC), the Canadian Institutes of Health Research (CIHR), the Government of Saskatchewan, and the University of Saskatchewan.

Funding information

Funding for this research was provided by: Saskatchewan Agricultural Development Fund; Natural Sciences and Engineering Research Council of Canada; Canada Foundation for Innovation; National Research Council of Canada; Canadian Institute for Health Research; Government of Saskatchewan; University of Saskatchewan.

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