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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161706
https://doi.org/10.1107/S2414314616017065

[1–9-NαC]-Linusorb B3 (cyclo­linopeptide A) aceto­nitrile disolvate

CROSSMARK_Color_square_no_text.svg
Jackson Mulenga Chitanda,a Jianfeng Zhu,b Philip Mausberg,a Peta-Gaye Gillian Burnetta and Martin J. T. Reaneya,c*

aDepartment of Plant Sciences, College of Agriculture and Bioresources, University of Saskatchewan, Saskatoon, Saskatchewan S7N 5A8, Canada, bSaskatchewan Structural Sciences Centre, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada, and cGuangdong Saskatchewan Oilseed Joint Laboratory, Department of Food Science and Engineering, Jinan University, Guangzhou, Guangdong 510632, People's Republic of China
*Correspondence e-mail: martin.reaney@usask.ca

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 18 October 2016; accepted 24 October 2016; online 8 November 2016)

The title compound, C57H85N9O9·2C2H3N [systematic name: cyclo-(prolyl-prolyl-phenyl­alanyl-phenyl­alanyl-leucyl-isoleucyl-isoleucylleucyl-val­yl) aceto­nitrile disolvate; synonym: cyclo­linopeptide aceto­nitrile disolvate], is a polypeptide with nine amino acids, viz. NαC-(Pro1–Pro2–Phe3–Phe4–Leu5–Ile6–Ile7–Leu8–Val9). It was extracted from flaxseed oil and crystallized from aceto­nitrile as a disolvate. In the title mol­ecule, there are four intra­molecular N—H⋯O hydrogen bonds. One of the two aceto­nitrile mol­ecules is hydrogen bonded to Phe3 via an N—H⋯N hydrogen bond, while the second aceto­nitrile mol­ecule is located at the other side of the peptide ring and is linked to the title mol­ecule by a C—H⋯N hydrogen bond. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming chains along the a-axis direction. The chains are linked by C—H⋯O hydrogen bonds, forming undulating layers parallel to the ac plane.

CCDC reference: 1511350

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

Structure description

Several cyclic peptides have been isolated from flaxseed (Linum usitatissimum L). The isolation and purification procedures used have been reported (Kaufmann & Tobschirbel, 1959[Kaufmann, H. P. & Tobschirbel, A. (1959). Chem. Ber. 92, 2805-2809.]; 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.]), as have the amino acid composition and sequencing methods (Prox & Weygand, 1966[Prox, A. & Weygand, F. (1966). Peptides. Proceedings of the 8th European Peptide Symposium, edited by H. C. Beyerman, A. van del Linde & W. Massen van den Brink, pp. 158-172. Amsterdam, New York: Elsevier/North-Holland Biomedical Press.]). Different solvents have been used to grow crystals of the title compound, and the crystal structures of a number of polymorphs have been reported. For example, different ortho­rhom­bic polymorphs have been obtained from chloro­form (Huben et al., 2014[Huben, K., Jewginski, M., Pabis, A., Paluch, P., Luy, B. & Jankowski, S. (2014). J. Pept. Sci. 20, 901-907.]), methanol (Quail et al., 2009[Quail, J. W., Shen, J., Reaney, M. J. T. & Sammynaiken, R. (2009). Acta Cryst. E65, o1913-o1914.]), methanol/2-propanol (Matsumoto et al., 2002[Matsumoto, T., Shishido, A., Morita, H., Itokawa, H. & Takeya, K. (2002). Tetrahedron, 58, 5135-5140.]), water/2-2-propanol (Di Blasio et al., 1987[Di Blasio, B., Benedetti, E., Pavone, V., Pedone, C. & Goodman, M. (1987). Biopolymers, 26, 2099-2101.], 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.]) and benzene/aceto­nitrile (Saviano et al., 1995[Saviano, M., Rossi, F., Filizola, M., Di Blasio, B. & Pedone, C. (1995). Acta Cryst. C51, 663-666.]). The last polymorph crystallized as an aceto­nitrile monosolvate monohydrate. It has been shown that the title compound tends to self-assemble, under suitable conditions, from zero-dimensional objects to one-dimensional nanofibers and finally producing a three-dimensional supra­molecular gel network (Rogers et al., 2016[Rogers, M. A., Feng, Q., Ladizhansky, V., Good, D. B., Smith, A. K., Corridini, M., Grahame, D. A. S., Bryksa, B. C., Jadhav, P. D., Sammynaiken, R., Lim, L. T., Guild, B., Shim, Y. Y., Burnett, P.-G. & Reaney, M. J. T. (2016). RSC Adv. 6, 40765-40776.]).

A systematic naming system specifically for the Type VI cyclic peptides, such as the title compound, that `reflects the taxonomic name of the species producing the orbitides and a numbering system that enables systematic representation of amino acid residues and modifications' has been proposed by our group (Shim et al., 2015[Shim, Y. Y., Young, L. W., Arnison, P. G., Gilding, E. & Reaney, M. J. T. (2015). J. Nat. Prod. 78, 645-652.]). Hence the name of the title compound [1–9-NαC]-linusorb B3 (cyclo­linopeptide A). Herein, we report on the crystal structure of a new ortho­rhom­bic polymorph of the title compound that crystallized as an acteo­nitrile disolvate.

The mol­ecular structure of the title [1–9-NαC]-linusorb B3 mol­ecule is illustrated in Fig. 1[link]. The peptide backbone ring is twisted to form four intra­molecular hydrogen bonds between the amino acids (N4—H4N⋯O9, N9—H9N⋯O4, N8—H8⋯O5 and N7—H7⋯O5), as shown in Fig. 1[link] and Table 1[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N4—H4N⋯O9 0.88 2.08 2.834 (5) 144
N7—H7⋯O4 0.88 2.30 3.112 (5) 153
N8—H8⋯O5 0.88 2.12 2.985 (5) 168
N9—H9N⋯O4 0.88 2.23 3.058 (5) 157
N3—H3⋯N1S 0.88 2.31 3.136 (7) 157
C13—H13A⋯N1S 0.99 2.67 3.451 (7) 136
N5—H5⋯O8i 0.88 2.60 3.103 (5) 117
N6—H6⋯O8i 0.88 2.42 3.153 (5) 141
C1—H1A⋯O3ii 0.99 2.48 3.378 (7) 150
C31—H31B⋯O8i 0.99 2.63 3.435 (6) 139
C37—H37⋯O7i 1.00 2.17 3.041 (6) 145
C53—H53⋯O3ii 1.00 2.35 3.187 (6) 140
C2S—H2S1⋯O6iii 0.98 2.37 3.268 (7) 152
C4S—H4S1⋯O5 0.98 2.55 3.463 (9) 155
C4S—H4S2⋯O6 0.98 2.62 3.246 (9) 122
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) [-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}].
[Figure 1]
Figure 1
Crystal structure of the title [1–9-NαC]-linusorb B3 mol­ecule, with atom labelling and 50% displacement ellipsoids. The intra­molecular hydrogen bonds (see Table 1[link]) are shown as dashed lines. For clarity, the solvent acteo­nitrile mol­ecules and the C-bound H atoms have been omitted.

In the crystal, one of the two aceto­nitrile mol­ecules is hydrogen bonded to phe3 via an N3—H3⋯N1S hydrogen bond (Table 1[link] and Fig. 2[link]). The second aceto­nitrile mol­ecule is located at the other side of the peptide ring and the C≡N bond is positioned proximate to a CHx-rich environment, and is linked to the title mol­ecule by a C—H⋯N hydrogen bond. The [1–9-NαC]-linusorb B3 mol­ecules are linked in chains along the a-axis direction by two inter­molecular hydrogen bonds, namely N5—H5⋯O8i and N6—H6⋯O8i (Table 1[link]), as shown in Fig. 2[link]. The chains are linked via C—H⋯O hydrogen bonds, forming undulating layers parallel to the ac plane (Fig. 3[link]).

[Figure 2]
Figure 2
A partial view along the b axis of the crystal packing of the title compound. The hydrogen bonds (see Table 1[link]) are shown as dashed lines, and, for clarity, the C-bound H atoms have been omitted.
[Figure 3]
Figure 3
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds (see Table 1[link]) are shown as dashed lines, and, for clarity, only the C-bound H atoms involved in hydrogen bonding have been included.

Synthesis and crystallization

Suitable crystals of the title compound were isolated from a solution of [1–9-NαC]-linusorb B3 in aceto­nitrile when the solvent was allowed to evaporate slowly at ambient temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The reflections 140, 038, 060, 119, 108, [\overline{1}]19, [\overline{1}]77 and 360 were affected by the beam-stop and were omitted from the final refinement.

Table 2
Experimental details

Crystal data
Chemical formula C57H85N9O9·2C2H3N
Mr 1122.44
Crystal system, space group Orthorhombic, P212121
Temperature (K) 100
a, b, c (Å) 9.6524 (6), 22.6947 (13), 29.0945 (17)
V (Å3) 6373.4 (7)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.64
Crystal size (mm) 0.55 × 0.06 × 0.06
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.587, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections 47444, 11348, 9085
Rint 0.086
(sin θ/λ)max (Å−1) 0.603
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.166, 1.05
No. of reflections 11348
No. of parameters 742
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.29, −0.31
Absolute structure Flack x determined using 3356 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 −0.16 (11)
Computer programs: APEX2 and SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXTL (Sheldrick 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]).

Structural data

CCDC reference: 1511350

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314616017065/su4085sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616017065/su4085Isup2.hkl

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

Cyclo-(prolyl-prolyl-phenylalanyl-phenylalanyl-leucyl-isoleucyl-isoleucylleucyl-valyl) acetonitrile disolvate top
Crystal data top
C57H85N9O9·2C2H3NDx = 1.170 Mg m−3
Mr = 1122.44Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 9122 reflections
a = 9.6524 (6) Åθ = 2.5–68.3°
b = 22.6947 (13) ŵ = 0.64 mm−1
c = 29.0945 (17) ÅT = 100 K
V = 6373.4 (7) Å3Rod, colourless
Z = 40.55 × 0.06 × 0.06 mm
F(000) = 2424
Data collection top
Bruker APEXII CCD
diffractometer		9085 reflections with I > 2σ(I)
φ and ω scansRint = 0.086
Absorption correction: multi-scan
(SADABS; Bruker, 2012)		θmax = 68.4°, θmin = 2.5°
Tmin = 0.587, Tmax = 0.753h = −11→6
47444 measured reflectionsk = −26→27
11348 independent reflectionsl = −33→34
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.0949P)2 + 1.8264P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
11348 reflectionsΔρmax = 0.29 e Å−3
742 parametersΔρmin = −0.31 e Å−3
0 restraintsAbsolute structure: Flack x determined using 3356 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: −0.16 (11)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.9530 (4)0.69914 (15)0.15822 (12)0.0353 (8)
O20.4072 (4)0.75979 (15)0.21331 (12)0.0371 (8)
O30.2530 (4)0.58487 (16)0.22979 (12)0.0350 (8)
O40.6377 (3)0.55765 (14)0.34502 (10)0.0259 (7)
O50.5884 (3)0.64306 (13)0.45172 (11)0.0270 (7)
O60.5764 (4)0.51419 (15)0.52030 (11)0.0321 (8)
O71.0051 (3)0.50867 (14)0.42400 (11)0.0297 (8)
O81.1564 (4)0.61766 (15)0.36511 (11)0.0311 (8)
O90.7741 (4)0.60902 (15)0.24898 (12)0.0329 (8)
N10.9425 (4)0.67747 (17)0.25304 (14)0.0278 (9)
N20.7444 (4)0.74399 (17)0.15876 (14)0.0290 (9)
N30.5053 (4)0.68133 (16)0.17730 (13)0.0254 (9)
H30.58190.66580.16620.031*
N40.4845 (4)0.59019 (15)0.24245 (13)0.0250 (9)
H4N0.56340.60670.23450.030*
N50.4659 (4)0.62382 (16)0.33677 (13)0.0241 (8)
H50.38930.63300.32200.029*
N60.4176 (4)0.58452 (16)0.42480 (12)0.0229 (8)
H60.36030.57730.40190.028*
N70.6405 (4)0.51027 (16)0.44540 (13)0.0235 (8)
H70.61440.51620.41680.028*
N80.8594 (4)0.58549 (16)0.43117 (12)0.0231 (8)
H80.77440.59700.43740.028*
N90.9410 (4)0.59572 (17)0.33834 (13)0.0263 (9)
H9N0.85290.59300.34590.032*
C11.0742 (6)0.7023 (2)0.26951 (19)0.0346 (12)
H1A1.15400.67920.25790.042*
H1B1.07730.70300.30350.042*
C21.0744 (6)0.7641 (2)0.24993 (19)0.0371 (12)
H2A1.12680.79150.26990.044*
H2B1.11480.76480.21870.044*
C30.9219 (6)0.7797 (2)0.24890 (18)0.0329 (11)
H3A0.90370.81250.22730.039*
H3B0.88820.79080.27990.039*
C40.8534 (5)0.7222 (2)0.23222 (17)0.0287 (11)
H40.75650.71890.24410.034*
C50.8555 (5)0.71933 (19)0.17980 (17)0.0280 (11)
C60.7463 (6)0.7547 (2)0.10845 (16)0.0342 (12)
H6A0.74490.71700.09130.041*
H6B0.82960.77730.09940.041*
C70.6159 (6)0.7898 (2)0.09956 (18)0.0382 (13)
H7A0.53710.76350.09220.046*
H7B0.62940.81790.07390.046*
C80.5911 (6)0.8225 (2)0.14493 (17)0.0337 (12)
H8A0.49310.83480.14800.040*
H8B0.65140.85760.14750.040*
C90.6295 (5)0.7757 (2)0.18099 (16)0.0277 (11)
H90.66360.79550.20950.033*
C100.5051 (5)0.7374 (2)0.19241 (16)0.0272 (11)
C110.3796 (5)0.6465 (2)0.17925 (16)0.0268 (10)
H110.29980.67460.18080.032*
C120.3674 (5)0.6048 (2)0.22016 (16)0.0270 (11)
C130.3627 (5)0.6099 (2)0.13493 (16)0.0261 (10)
H13A0.44440.58400.13120.031*
H13B0.27980.58450.13790.031*
C140.3478 (5)0.6482 (2)0.09237 (15)0.0265 (10)
C150.4476 (6)0.6463 (2)0.05815 (16)0.0313 (11)
H150.52630.62160.06160.038*
C160.4331 (7)0.6806 (2)0.01861 (18)0.0403 (14)
H160.50100.6787−0.00500.048*
C170.3207 (7)0.7169 (2)0.01388 (19)0.0430 (15)
H170.31210.7412−0.01260.052*
C180.2198 (7)0.7183 (2)0.04750 (19)0.0423 (14)
H180.14010.74230.04360.051*
C190.2348 (6)0.6847 (2)0.08716 (17)0.0325 (12)
H190.16680.68680.11070.039*
C200.4821 (5)0.54731 (19)0.27970 (15)0.0236 (10)
H200.38300.53680.28540.028*
C210.5373 (5)0.57641 (19)0.32338 (15)0.0221 (10)
C220.5582 (5)0.4906 (2)0.26685 (16)0.0287 (11)
H22A0.65620.49960.25970.034*
H22B0.55620.46280.29310.034*
C230.4892 (6)0.46284 (19)0.22550 (17)0.0294 (11)
C240.5391 (6)0.4724 (2)0.18170 (17)0.0348 (12)
H240.62330.49340.17750.042*
C250.4671 (7)0.4515 (2)0.14341 (18)0.0450 (15)
H250.50320.45780.11340.054*
C260.3453 (7)0.4220 (2)0.1488 (2)0.0457 (15)
H260.29550.40900.12260.055*
C270.2942 (6)0.4111 (2)0.1919 (2)0.0421 (14)
H270.21070.38940.19560.050*
C280.3660 (6)0.4320 (2)0.23042 (19)0.0356 (12)
H280.32980.42510.26030.043*
C290.5101 (5)0.66102 (19)0.37490 (15)0.0239 (10)
H290.60810.67300.36890.029*
C300.5073 (5)0.62878 (19)0.42061 (15)0.0232 (10)
C310.4234 (5)0.7166 (2)0.37657 (16)0.0266 (10)
H31A0.45530.74090.40270.032*
H31B0.32600.70540.38260.032*
C320.4282 (5)0.7545 (2)0.33260 (16)0.0282 (11)
H320.38180.73190.30740.034*
C330.5744 (6)0.7671 (2)0.31781 (19)0.0409 (13)
H33A0.57340.79400.29150.061*
H33B0.61990.73020.30900.061*
H33C0.62520.78520.34330.061*
C340.3463 (6)0.8111 (2)0.3403 (2)0.0401 (13)
H34A0.38960.83400.36500.060*
H34B0.25090.80130.34900.060*
H34C0.34570.83440.31200.060*
C350.4103 (5)0.54745 (19)0.46583 (15)0.0232 (10)
H350.37650.57260.49170.028*
C360.5510 (5)0.52287 (19)0.47959 (16)0.0251 (10)
C370.3024 (5)0.4991 (2)0.45781 (16)0.0249 (10)
H370.21370.51960.45010.030*
C380.2740 (6)0.4624 (2)0.50061 (17)0.0327 (11)
H38A0.20510.43160.49290.039*
H38B0.36070.44230.50990.039*
C390.2204 (7)0.4982 (2)0.5410 (2)0.0447 (15)
H39A0.29270.52530.55150.067*
H39B0.19520.47150.56620.067*
H39C0.13870.52070.53150.067*
C400.3364 (6)0.4590 (2)0.41696 (17)0.0317 (11)
H40A0.41940.43580.42390.048*
H40B0.35310.48310.38960.048*
H40C0.25830.43230.41130.048*
C410.7780 (5)0.4874 (2)0.45410 (17)0.0255 (10)
H410.79030.48700.48820.031*
C420.8912 (5)0.5279 (2)0.43471 (16)0.0249 (10)
C430.7972 (5)0.4237 (2)0.43773 (18)0.0321 (11)
H430.89660.41280.44240.039*
C440.7639 (6)0.4165 (2)0.38658 (19)0.0361 (12)
H44A0.66220.41850.38250.043*
H44B0.80510.44990.36950.043*
C450.8158 (7)0.3598 (3)0.3658 (2)0.0533 (16)
H45A0.91690.35820.36840.080*
H45B0.78920.35810.33330.080*
H45C0.77490.32630.38220.080*
C460.7089 (6)0.3826 (2)0.4677 (2)0.0411 (13)
H46A0.61130.39400.46530.062*
H46B0.73910.38570.49980.062*
H46C0.72010.34190.45710.062*
C470.9618 (5)0.62935 (19)0.41727 (16)0.0252 (10)
H470.90960.66670.41140.030*
C481.0320 (5)0.6122 (2)0.37119 (16)0.0258 (10)
C491.0681 (5)0.6434 (2)0.45468 (16)0.0263 (10)
H49A1.13230.60960.45750.032*
H49B1.12320.67790.44480.032*
C501.0069 (5)0.6563 (2)0.50175 (17)0.0307 (11)
H500.95950.61980.51280.037*
C510.9008 (6)0.7058 (3)0.5012 (2)0.0436 (14)
H51A0.94320.74150.48840.065*
H51B0.86910.71360.53260.065*
H51C0.82160.69420.48210.065*
C521.1236 (6)0.6707 (2)0.53541 (18)0.0351 (12)
H52A1.19630.64070.53300.053*
H52B1.08690.67120.56680.053*
H52C1.16250.70950.52800.053*
C530.9795 (5)0.5821 (2)0.29114 (16)0.0285 (11)
H531.07960.59170.28650.034*
C540.8905 (5)0.6238 (2)0.26157 (16)0.0273 (11)
C550.9558 (5)0.5164 (2)0.28067 (17)0.0303 (11)
H550.86010.50580.29090.036*
C561.0589 (6)0.4799 (2)0.30845 (18)0.0357 (12)
H56A1.04010.43790.30370.054*
H56B1.04940.48950.34120.054*
H56C1.15330.48900.29830.054*
C570.9683 (6)0.5025 (2)0.22992 (18)0.0388 (13)
H57A0.89950.52530.21270.058*
H57B0.95200.46030.22500.058*
H57C1.06140.51280.21920.058*
C1S0.8290 (6)0.5854 (2)0.12039 (18)0.0355 (12)
C2S0.9706 (6)0.5686 (3)0.1108 (2)0.0489 (15)
H2S10.97140.53390.09080.073*
H2S21.01790.55930.13970.073*
H2S31.01830.60130.09550.073*
C3S0.4920 (9)0.6854 (3)0.5991 (3)0.068 (2)
C4S0.5619 (11)0.6418 (4)0.5704 (3)0.088 (3)
H4S10.56330.65550.53850.131*
H4S20.51210.60420.57220.131*
H4S30.65710.63640.58130.131*
N1S0.7185 (5)0.5986 (2)0.12775 (17)0.0437 (12)
N2S0.4386 (8)0.7210 (3)0.6218 (2)0.086 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.034 (2)0.0395 (19)0.032 (2)0.0004 (16)0.0068 (16)−0.0039 (15)
O20.041 (2)0.0338 (18)0.036 (2)0.0014 (16)0.0054 (16)−0.0083 (16)
O30.024 (2)0.048 (2)0.033 (2)−0.0012 (16)0.0033 (15)0.0133 (16)
O40.0266 (18)0.0322 (16)0.0188 (17)0.0017 (14)−0.0005 (14)−0.0004 (13)
O50.0324 (19)0.0253 (15)0.0234 (18)−0.0024 (14)−0.0041 (14)−0.0028 (13)
O60.033 (2)0.0434 (19)0.0199 (19)0.0029 (16)−0.0015 (14)0.0056 (14)
O70.0212 (19)0.0322 (17)0.036 (2)0.0024 (15)−0.0032 (14)−0.0001 (14)
O80.024 (2)0.0426 (19)0.0262 (18)−0.0033 (15)−0.0004 (14)−0.0019 (15)
O90.029 (2)0.0381 (18)0.0311 (19)−0.0088 (15)−0.0047 (15)0.0056 (15)
N10.024 (2)0.033 (2)0.027 (2)−0.0026 (17)−0.0006 (17)−0.0008 (17)
N20.035 (2)0.028 (2)0.025 (2)0.0025 (18)0.0012 (17)0.0008 (17)
N30.029 (2)0.0278 (19)0.019 (2)0.0003 (17)0.0026 (16)0.0006 (15)
N40.028 (2)0.0234 (18)0.024 (2)−0.0012 (16)−0.0006 (16)−0.0006 (15)
N50.026 (2)0.0272 (19)0.019 (2)0.0025 (17)−0.0039 (16)0.0006 (15)
N60.025 (2)0.0258 (19)0.0182 (19)−0.0008 (17)−0.0027 (15)0.0013 (15)
N70.024 (2)0.0261 (19)0.020 (2)−0.0001 (17)−0.0013 (16)−0.0015 (15)
N80.020 (2)0.0252 (19)0.024 (2)0.0009 (16)−0.0025 (16)−0.0019 (15)
N90.023 (2)0.033 (2)0.022 (2)−0.0006 (17)0.0016 (16)−0.0022 (16)
C10.031 (3)0.035 (3)0.038 (3)−0.004 (2)−0.003 (2)0.000 (2)
C20.043 (3)0.034 (3)0.034 (3)−0.006 (2)−0.007 (2)−0.001 (2)
C30.039 (3)0.030 (2)0.029 (3)0.000 (2)−0.004 (2)−0.002 (2)
C40.028 (3)0.031 (2)0.027 (3)0.003 (2)−0.001 (2)0.0010 (19)
C50.031 (3)0.024 (2)0.030 (3)−0.003 (2)0.001 (2)0.000 (2)
C60.047 (3)0.037 (3)0.018 (3)−0.003 (2)0.002 (2)0.003 (2)
C70.053 (4)0.034 (3)0.027 (3)−0.007 (2)−0.005 (2)0.004 (2)
C80.041 (3)0.027 (2)0.033 (3)0.002 (2)−0.001 (2)0.007 (2)
C90.033 (3)0.023 (2)0.026 (3)0.004 (2)−0.002 (2)−0.0024 (19)
C100.034 (3)0.027 (2)0.021 (2)0.002 (2)−0.001 (2)0.0018 (19)
C110.028 (3)0.029 (2)0.023 (2)−0.004 (2)−0.0011 (19)0.0024 (19)
C120.031 (3)0.028 (2)0.022 (2)0.003 (2)0.001 (2)−0.0060 (19)
C130.029 (3)0.027 (2)0.023 (2)−0.002 (2)−0.003 (2)0.0017 (19)
C140.036 (3)0.023 (2)0.021 (2)−0.005 (2)−0.003 (2)−0.0002 (18)
C150.044 (3)0.026 (2)0.024 (3)−0.005 (2)0.003 (2)0.000 (2)
C160.060 (4)0.036 (3)0.024 (3)−0.013 (3)0.004 (3)−0.003 (2)
C170.076 (5)0.028 (3)0.025 (3)−0.009 (3)−0.007 (3)0.005 (2)
C180.059 (4)0.034 (3)0.034 (3)0.006 (3)−0.013 (3)0.002 (2)
C190.039 (3)0.030 (3)0.028 (3)−0.001 (2)−0.003 (2)0.000 (2)
C200.028 (3)0.023 (2)0.019 (2)−0.0024 (19)−0.0014 (19)0.0022 (17)
C210.024 (3)0.024 (2)0.019 (2)−0.0009 (19)0.0017 (19)0.0051 (18)
C220.034 (3)0.027 (2)0.025 (3)0.003 (2)−0.006 (2)−0.0001 (19)
C230.040 (3)0.021 (2)0.027 (3)0.006 (2)−0.003 (2)−0.0034 (18)
C240.052 (4)0.024 (2)0.028 (3)0.003 (2)0.002 (2)−0.001 (2)
C250.076 (5)0.036 (3)0.022 (3)0.019 (3)−0.002 (3)−0.002 (2)
C260.067 (4)0.029 (3)0.042 (3)0.009 (3)−0.019 (3)−0.011 (2)
C270.044 (4)0.028 (3)0.055 (4)0.004 (2)−0.014 (3)−0.013 (2)
C280.043 (3)0.025 (2)0.038 (3)0.002 (2)−0.001 (2)−0.005 (2)
C290.027 (3)0.025 (2)0.019 (2)−0.0042 (19)0.0006 (19)−0.0019 (17)
C300.022 (3)0.026 (2)0.022 (2)0.0018 (19)0.0002 (19)−0.0060 (17)
C310.030 (3)0.026 (2)0.023 (3)−0.001 (2)0.002 (2)−0.0017 (18)
C320.036 (3)0.026 (2)0.022 (2)−0.002 (2)−0.004 (2)−0.0005 (19)
C330.054 (4)0.037 (3)0.032 (3)−0.007 (3)0.006 (3)0.006 (2)
C340.054 (4)0.026 (2)0.040 (3)0.000 (2)−0.012 (3)0.002 (2)
C350.026 (3)0.025 (2)0.018 (2)0.001 (2)0.0031 (19)0.0001 (18)
C360.029 (3)0.023 (2)0.023 (3)−0.0001 (19)−0.002 (2)−0.0004 (18)
C370.023 (3)0.025 (2)0.027 (3)0.0028 (19)0.0005 (19)−0.0011 (19)
C380.035 (3)0.030 (2)0.033 (3)−0.002 (2)0.005 (2)0.006 (2)
C390.062 (4)0.036 (3)0.037 (3)−0.005 (3)0.017 (3)0.007 (2)
C400.034 (3)0.030 (2)0.032 (3)−0.001 (2)−0.003 (2)−0.005 (2)
C410.023 (3)0.029 (2)0.024 (3)0.002 (2)−0.0027 (19)0.0009 (19)
C420.022 (3)0.030 (2)0.022 (2)−0.003 (2)−0.0058 (19)−0.0002 (19)
C430.029 (3)0.027 (2)0.041 (3)0.003 (2)−0.001 (2)0.003 (2)
C440.033 (3)0.030 (2)0.046 (3)−0.005 (2)0.001 (2)−0.006 (2)
C450.057 (4)0.037 (3)0.066 (4)0.002 (3)0.004 (3)−0.017 (3)
C460.041 (3)0.028 (3)0.055 (4)−0.002 (2)0.002 (3)0.005 (2)
C470.029 (3)0.021 (2)0.027 (3)0.0000 (19)0.001 (2)−0.0010 (18)
C480.029 (3)0.026 (2)0.023 (2)−0.002 (2)−0.003 (2)0.0026 (18)
C490.027 (3)0.026 (2)0.027 (3)−0.003 (2)0.000 (2)−0.0027 (19)
C500.032 (3)0.033 (2)0.027 (3)−0.003 (2)−0.003 (2)−0.002 (2)
C510.046 (4)0.047 (3)0.037 (3)0.009 (3)−0.009 (3)−0.017 (3)
C520.040 (3)0.035 (3)0.030 (3)0.001 (2)−0.005 (2)−0.004 (2)
C530.028 (3)0.031 (2)0.026 (3)−0.003 (2)−0.001 (2)−0.003 (2)
C540.026 (3)0.035 (3)0.021 (2)−0.001 (2)0.0046 (19)−0.0010 (19)
C550.030 (3)0.032 (2)0.029 (3)−0.001 (2)0.002 (2)−0.004 (2)
C560.037 (3)0.035 (3)0.035 (3)0.003 (2)0.004 (2)−0.005 (2)
C570.042 (3)0.045 (3)0.030 (3)−0.001 (2)0.000 (2)−0.009 (2)
C1S0.037 (4)0.040 (3)0.029 (3)−0.005 (3)−0.003 (2)−0.002 (2)
C2S0.038 (4)0.060 (4)0.049 (4)0.003 (3)0.006 (3)−0.015 (3)
C3S0.090 (6)0.062 (4)0.052 (4)0.002 (4)−0.004 (4)−0.006 (4)
C4S0.117 (7)0.080 (5)0.066 (5)0.007 (5)−0.016 (5)−0.029 (4)
N1S0.036 (3)0.045 (3)0.049 (3)0.000 (2)0.001 (2)0.001 (2)
N2S0.109 (6)0.086 (5)0.062 (4)0.022 (4)−0.001 (4)−0.008 (4)
Geometric parameters (Å, º) top
O1—C51.221 (6)C26—C271.369 (9)
O2—C101.233 (6)C26—H260.9500
O3—C121.226 (6)C27—C281.402 (8)
O4—C211.232 (5)C27—H270.9500
O5—C301.240 (5)C28—H280.9500
O6—C361.226 (6)C29—C311.514 (7)
O7—C421.223 (6)C29—C301.518 (6)
O8—C481.220 (6)C29—H291.0000
O9—C541.229 (6)C31—C321.542 (6)
N1—C541.340 (6)C31—H31A0.9900
N1—C41.462 (6)C31—H31B0.9900
N1—C11.470 (7)C32—C331.503 (8)
N2—C51.355 (6)C32—C341.525 (7)
N2—C91.472 (6)C32—H321.0000
N2—C61.484 (6)C33—H33A0.9800
N3—C101.347 (6)C33—H33B0.9800
N3—C111.449 (6)C33—H33C0.9800
N3—H30.8800C34—H34A0.9800
N4—C121.345 (6)C34—H34B0.9800
N4—C201.457 (6)C34—H34C0.9800
N4—H4N0.8800C35—C361.522 (7)
N5—C211.336 (6)C35—C371.530 (6)
N5—C291.458 (6)C35—H351.0000
N5—H50.8800C37—C381.523 (7)
N6—C301.332 (6)C37—C401.533 (7)
N6—C351.462 (6)C37—H371.0000
N6—H60.8800C38—C391.520 (8)
N7—C361.348 (6)C38—H38A0.9900
N7—C411.448 (6)C38—H38B0.9900
N7—H70.8800C39—H39A0.9800
N8—C421.346 (6)C39—H39B0.9800
N8—C471.460 (6)C39—H39C0.9800
N8—H80.8800C40—H40A0.9800
N9—C481.351 (6)C40—H40B0.9800
N9—C531.456 (6)C40—H40C0.9800
N9—H9N0.8800C41—C431.533 (7)
C1—C21.515 (7)C41—C421.536 (7)
C1—H1A0.9900C41—H411.0000
C1—H1B0.9900C43—C441.531 (8)
C2—C31.514 (8)C43—C461.535 (7)
C2—H2A0.9900C43—H431.0000
C2—H2B0.9900C44—C451.506 (7)
C3—C41.541 (7)C44—H44A0.9900
C3—H3A0.9900C44—H44B0.9900
C3—H3B0.9900C45—H45A0.9800
C4—C51.527 (7)C45—H45B0.9800
C4—H41.0000C45—H45C0.9800
C6—C71.512 (8)C46—H46A0.9800
C6—H6A0.9900C46—H46B0.9800
C6—H6B0.9900C46—H46C0.9800
C7—C81.533 (7)C47—C491.529 (7)
C7—H7A0.9900C47—C481.552 (7)
C7—H7B0.9900C47—H471.0000
C8—C91.538 (7)C49—C501.520 (7)
C8—H8A0.9900C49—H49A0.9900
C8—H8B0.9900C49—H49B0.9900
C9—C101.519 (7)C50—C511.520 (8)
C9—H91.0000C50—C521.528 (7)
C11—C121.526 (7)C50—H501.0000
C11—C131.542 (7)C51—H51A0.9800
C11—H111.0000C51—H51B0.9800
C13—C141.519 (6)C51—H51C0.9800
C13—H13A0.9900C52—H52A0.9800
C13—H13B0.9900C52—H52B0.9800
C14—C191.378 (7)C52—H52C0.9800
C14—C151.386 (7)C53—C551.538 (7)
C15—C161.396 (7)C53—C541.541 (7)
C15—H150.9500C53—H531.0000
C16—C171.370 (9)C55—C571.515 (7)
C16—H160.9500C55—C561.526 (7)
C17—C181.380 (9)C55—H551.0000
C17—H170.9500C56—H56A0.9800
C18—C191.391 (7)C56—H56B0.9800
C18—H180.9500C56—H56C0.9800
C19—H190.9500C57—H57A0.9800
C20—C221.528 (6)C57—H57B0.9800
C20—C211.528 (6)C57—H57C0.9800
C20—H201.0000C1S—N1S1.128 (7)
C22—C231.513 (7)C1S—C2S1.445 (9)
C22—H22A0.9900C2S—H2S10.9800
C22—H22B0.9900C2S—H2S20.9800
C23—C241.380 (7)C2S—H2S30.9800
C23—C281.387 (8)C3S—N2S1.164 (10)
C24—C251.397 (8)C3S—C4S1.458 (11)
C24—H240.9500C4S—H4S10.9800
C25—C261.361 (9)C4S—H4S20.9800
C25—H250.9500C4S—H4S30.9800
C54—N1—C4119.1 (4)C32—C31—H31B108.5
C54—N1—C1127.7 (4)H31A—C31—H31B107.5
C4—N1—C1112.2 (4)C33—C32—C34111.7 (4)
C5—N2—C9126.8 (4)C33—C32—C31111.8 (4)
C5—N2—C6120.2 (4)C34—C32—C31109.4 (4)
C9—N2—C6111.3 (4)C33—C32—H32108.0
C10—N3—C11120.1 (4)C34—C32—H32108.0
C10—N3—H3120.0C31—C32—H32108.0
C11—N3—H3120.0C32—C33—H33A109.5
C12—N4—C20120.6 (4)C32—C33—H33B109.5
C12—N4—H4N119.7H33A—C33—H33B109.5
C20—N4—H4N119.7C32—C33—H33C109.5
C21—N5—C29122.5 (4)H33A—C33—H33C109.5
C21—N5—H5118.7H33B—C33—H33C109.5
C29—N5—H5118.7C32—C34—H34A109.5
C30—N6—C35122.7 (4)C32—C34—H34B109.5
C30—N6—H6118.7H34A—C34—H34B109.5
C35—N6—H6118.7C32—C34—H34C109.5
C36—N7—C41122.3 (4)H34A—C34—H34C109.5
C36—N7—H7118.8H34B—C34—H34C109.5
C41—N7—H7118.8N6—C35—C36112.5 (4)
C42—N8—C47121.9 (4)N6—C35—C37108.7 (4)
C42—N8—H8119.0C36—C35—C37112.6 (4)
C47—N8—H8119.0N6—C35—H35107.6
C48—N9—C53124.0 (4)C36—C35—H35107.6
C48—N9—H9N118.0C37—C35—H35107.6
C53—N9—H9N118.0O6—C36—N7123.4 (5)
N1—C1—C2103.5 (4)O6—C36—C35119.5 (4)
N1—C1—H1A111.1N7—C36—C35117.1 (4)
C2—C1—H1A111.1C38—C37—C35113.0 (4)
N1—C1—H1B111.1C38—C37—C40110.3 (4)
C2—C1—H1B111.1C35—C37—C40113.5 (4)
H1A—C1—H1B109.0C38—C37—H37106.5
C3—C2—C1102.8 (4)C35—C37—H37106.5
C3—C2—H2A111.2C40—C37—H37106.5
C1—C2—H2A111.2C39—C38—C37113.7 (4)
C3—C2—H2B111.2C39—C38—H38A108.8
C1—C2—H2B111.2C37—C38—H38A108.8
H2A—C2—H2B109.1C39—C38—H38B108.8
C2—C3—C4103.1 (4)C37—C38—H38B108.8
C2—C3—H3A111.2H38A—C38—H38B107.7
C4—C3—H3A111.2C38—C39—H39A109.5
C2—C3—H3B111.2C38—C39—H39B109.5
C4—C3—H3B111.2H39A—C39—H39B109.5
H3A—C3—H3B109.1C38—C39—H39C109.5
N1—C4—C5112.1 (4)H39A—C39—H39C109.5
N1—C4—C3101.8 (4)H39B—C39—H39C109.5
C5—C4—C3110.2 (4)C37—C40—H40A109.5
N1—C4—H4110.8C37—C40—H40B109.5
C5—C4—H4110.8H40A—C40—H40B109.5
C3—C4—H4110.8C37—C40—H40C109.5
O1—C5—N2122.2 (5)H40A—C40—H40C109.5
O1—C5—C4122.6 (5)H40B—C40—H40C109.5
N2—C5—C4115.1 (4)N7—C41—C43113.2 (4)
N2—C6—C7104.2 (4)N7—C41—C42111.9 (4)
N2—C6—H6A110.9C43—C41—C42111.4 (4)
C7—C6—H6A110.9N7—C41—H41106.6
N2—C6—H6B110.9C43—C41—H41106.6
C7—C6—H6B110.9C42—C41—H41106.6
H6A—C6—H6B108.9O7—C42—N8122.1 (4)
C6—C7—C8103.8 (4)O7—C42—C41121.3 (4)
C6—C7—H7A111.0N8—C42—C41116.6 (4)
C8—C7—H7A111.0C44—C43—C41112.2 (4)
C6—C7—H7B111.0C44—C43—C46111.8 (4)
C8—C7—H7B111.0C41—C43—C46109.2 (4)
H7A—C7—H7B109.0C44—C43—H43107.8
C7—C8—C9102.5 (4)C41—C43—H43107.8
C7—C8—H8A111.3C46—C43—H43107.8
C9—C8—H8A111.3C45—C44—C43114.3 (5)
C7—C8—H8B111.3C45—C44—H44A108.7
C9—C8—H8B111.3C43—C44—H44A108.7
H8A—C8—H8B109.2C45—C44—H44B108.7
N2—C9—C10114.3 (4)C43—C44—H44B108.7
N2—C9—C8102.7 (4)H44A—C44—H44B107.6
C10—C9—C8110.7 (4)C44—C45—H45A109.5
N2—C9—H9109.6C44—C45—H45B109.5
C10—C9—H9109.6H45A—C45—H45B109.5
C8—C9—H9109.6C44—C45—H45C109.5
O2—C10—N3123.5 (5)H45A—C45—H45C109.5
O2—C10—C9118.5 (4)H45B—C45—H45C109.5
N3—C10—C9117.9 (4)C43—C46—H46A109.5
N3—C11—C12115.7 (4)C43—C46—H46B109.5
N3—C11—C13110.4 (4)H46A—C46—H46B109.5
C12—C11—C13108.1 (4)C43—C46—H46C109.5
N3—C11—H11107.4H46A—C46—H46C109.5
C12—C11—H11107.4H46B—C46—H46C109.5
C13—C11—H11107.4N8—C47—C49113.5 (4)
O3—C12—N4123.8 (4)N8—C47—C48111.4 (4)
O3—C12—C11118.5 (4)C49—C47—C48112.0 (4)
N4—C12—C11117.7 (4)N8—C47—H47106.5
C14—C13—C11112.6 (4)C49—C47—H47106.5
C14—C13—H13A109.1C48—C47—H47106.5
C11—C13—H13A109.1O8—C48—N9124.4 (4)
C14—C13—H13B109.1O8—C48—C47122.0 (4)
C11—C13—H13B109.1N9—C48—C47113.4 (4)
H13A—C13—H13B107.8C50—C49—C47114.9 (4)
C19—C14—C15119.3 (4)C50—C49—H49A108.5
C19—C14—C13120.5 (5)C47—C49—H49A108.5
C15—C14—C13120.1 (4)C50—C49—H49B108.5
C14—C15—C16120.3 (5)C47—C49—H49B108.5
C14—C15—H15119.8H49A—C49—H49B107.5
C16—C15—H15119.8C51—C50—C49113.2 (4)
C17—C16—C15119.8 (5)C51—C50—C52110.2 (4)
C17—C16—H16120.1C49—C50—C52109.4 (4)
C15—C16—H16120.1C51—C50—H50107.9
C16—C17—C18120.1 (5)C49—C50—H50107.9
C16—C17—H17119.9C52—C50—H50107.9
C18—C17—H17119.9C50—C51—H51A109.5
C17—C18—C19120.1 (6)C50—C51—H51B109.5
C17—C18—H18119.9H51A—C51—H51B109.5
C19—C18—H18119.9C50—C51—H51C109.5
C14—C19—C18120.2 (5)H51A—C51—H51C109.5
C14—C19—H19119.9H51B—C51—H51C109.5
C18—C19—H19119.9C50—C52—H52A109.5
N4—C20—C22111.9 (4)C50—C52—H52B109.5
N4—C20—C21108.9 (3)H52A—C52—H52B109.5
C22—C20—C21113.6 (4)C50—C52—H52C109.5
N4—C20—H20107.4H52A—C52—H52C109.5
C22—C20—H20107.4H52B—C52—H52C109.5
C21—C20—H20107.4N9—C53—C55110.8 (4)
O4—C21—N5122.3 (4)N9—C53—C54104.7 (4)
O4—C21—C20123.4 (4)C55—C53—C54113.7 (4)
N5—C21—C20114.3 (4)N9—C53—H53109.2
C23—C22—C20109.5 (4)C55—C53—H53109.2
C23—C22—H22A109.8C54—C53—H53109.2
C20—C22—H22A109.8O9—C54—N1122.4 (5)
C23—C22—H22B109.8O9—C54—C53120.5 (4)
C20—C22—H22B109.8N1—C54—C53116.9 (4)
H22A—C22—H22B108.2C57—C55—C56110.5 (4)
C24—C23—C28118.3 (5)C57—C55—C53112.6 (4)
C24—C23—C22121.0 (5)C56—C55—C53108.9 (4)
C28—C23—C22120.4 (5)C57—C55—H55108.2
C23—C24—C25120.7 (5)C56—C55—H55108.2
C23—C24—H24119.7C53—C55—H55108.2
C25—C24—H24119.7C55—C56—H56A109.5
C26—C25—C24120.3 (5)C55—C56—H56B109.5
C26—C25—H25119.9H56A—C56—H56B109.5
C24—C25—H25119.9C55—C56—H56C109.5
C25—C26—C27120.5 (5)H56A—C56—H56C109.5
C25—C26—H26119.8H56B—C56—H56C109.5
C27—C26—H26119.8C55—C57—H57A109.5
C26—C27—C28119.5 (6)C55—C57—H57B109.5
C26—C27—H27120.3H57A—C57—H57B109.5
C28—C27—H27120.3C55—C57—H57C109.5
C23—C28—C27120.8 (5)H57A—C57—H57C109.5
C23—C28—H28119.6H57B—C57—H57C109.5
C27—C28—H28119.6N1S—C1S—C2S179.8 (8)
N5—C29—C31110.2 (4)C1S—C2S—H2S1109.5
N5—C29—C30112.5 (4)C1S—C2S—H2S2109.5
C31—C29—C30111.3 (4)H2S1—C2S—H2S2109.5
N5—C29—H29107.5C1S—C2S—H2S3109.5
C31—C29—H29107.5H2S1—C2S—H2S3109.5
C30—C29—H29107.5H2S2—C2S—H2S3109.5
O5—C30—N6122.7 (4)N2S—C3S—C4S178.5 (10)
O5—C30—C29120.2 (4)C3S—C4S—H4S1109.5
N6—C30—C29117.1 (4)C3S—C4S—H4S2109.5
C29—C31—C32114.9 (4)H4S1—C4S—H4S2109.5
C29—C31—H31A108.5C3S—C4S—H4S3109.5
C32—C31—H31A108.5H4S1—C4S—H4S3109.5
C29—C31—H31B108.5H4S2—C4S—H4S3109.5
C54—N1—C1—C2−178.5 (5)C25—C26—C27—C282.1 (8)
C4—N1—C1—C2−10.0 (5)C24—C23—C28—C270.1 (7)
N1—C1—C2—C331.4 (5)C22—C23—C28—C27173.7 (5)
C1—C2—C3—C4−41.0 (5)C26—C27—C28—C23−1.1 (7)
C54—N1—C4—C5−87.7 (5)C21—N5—C29—C31170.1 (4)
C1—N1—C4—C5102.7 (5)C21—N5—C29—C30−65.0 (5)
C54—N1—C4—C3154.5 (4)C35—N6—C30—O5−2.3 (7)
C1—N1—C4—C3−15.1 (5)C35—N6—C30—C29176.0 (4)
C2—C3—C4—N134.2 (5)N5—C29—C30—O5151.1 (4)
C2—C3—C4—C5−84.9 (5)C31—C29—C30—O5−84.7 (5)
C9—N2—C5—O1−172.3 (4)N5—C29—C30—N6−27.2 (6)
C6—N2—C5—O1−8.4 (7)C31—C29—C30—N696.9 (5)
C9—N2—C5—C44.1 (6)N5—C29—C31—C32−58.5 (5)
C6—N2—C5—C4168.0 (4)C30—C29—C31—C32176.0 (4)
N1—C4—C5—O1−25.4 (6)C29—C31—C32—C33−51.3 (6)
C3—C4—C5—O187.3 (5)C29—C31—C32—C34−175.5 (4)
N1—C4—C5—N2158.3 (4)C30—N6—C35—C36−51.3 (5)
C3—C4—C5—N2−89.1 (5)C30—N6—C35—C37−176.7 (4)
C5—N2—C6—C7−172.2 (4)C41—N7—C36—O6−2.6 (7)
C9—N2—C6—C7−6.0 (5)C41—N7—C36—C35179.2 (4)
N2—C6—C7—C828.2 (5)N6—C35—C36—O6148.2 (4)
C6—C7—C8—C9−39.5 (5)C37—C35—C36—O6−88.5 (5)
C5—N2—C9—C10−93.4 (5)N6—C35—C36—N7−33.5 (5)
C6—N2—C9—C10101.5 (5)C37—C35—C36—N789.7 (5)
C5—N2—C9—C8146.6 (5)N6—C35—C37—C38−173.1 (4)
C6—N2—C9—C8−18.5 (5)C36—C35—C37—C3861.5 (5)
C7—C8—C9—N235.1 (5)N6—C35—C37—C4060.4 (5)
C7—C8—C9—C10−87.4 (5)C36—C35—C37—C40−65.0 (5)
C11—N3—C10—O29.1 (7)C35—C37—C38—C3959.7 (6)
C11—N3—C10—C9−167.9 (4)C40—C37—C38—C39−172.1 (5)
N2—C9—C10—O2176.2 (4)C36—N7—C41—C43112.4 (5)
C8—C9—C10—O2−68.5 (6)C36—N7—C41—C42−120.7 (4)
N2—C9—C10—N3−6.7 (6)C47—N8—C42—O7−4.2 (7)
C8—C9—C10—N3108.7 (5)C47—N8—C42—C41174.3 (4)
C10—N3—C11—C12−98.5 (5)N7—C41—C42—O7−154.2 (4)
C10—N3—C11—C13138.4 (4)C43—C41—C42—O7−26.3 (6)
C20—N4—C12—O31.7 (7)N7—C41—C42—N827.3 (6)
C20—N4—C12—C11−175.6 (4)C43—C41—C42—N8155.2 (4)
N3—C11—C12—O3163.1 (4)N7—C41—C43—C4456.3 (6)
C13—C11—C12—O3−72.6 (5)C42—C41—C43—C44−70.9 (5)
N3—C11—C12—N4−19.5 (6)N7—C41—C43—C46−68.2 (5)
C13—C11—C12—N4104.8 (5)C42—C41—C43—C46164.6 (4)
N3—C11—C13—C14−62.6 (5)C41—C43—C44—C45164.7 (5)
C12—C11—C13—C14170.0 (4)C46—C43—C44—C45−72.2 (6)
C11—C13—C14—C19−64.5 (6)C42—N8—C47—C49−73.9 (5)
C11—C13—C14—C15116.0 (5)C42—N8—C47—C4853.6 (5)
C19—C14—C15—C16−0.7 (7)C53—N9—C48—O80.1 (7)
C13—C14—C15—C16178.9 (4)C53—N9—C48—C47174.9 (4)
C14—C15—C16—C171.0 (7)N8—C47—C48—O8−137.5 (5)
C15—C16—C17—C18−1.9 (8)C49—C47—C48—O8−9.2 (6)
C16—C17—C18—C192.6 (8)N8—C47—C48—N947.5 (5)
C15—C14—C19—C181.3 (7)C49—C47—C48—N9175.8 (4)
C13—C14—C19—C18−178.2 (4)N8—C47—C49—C50−48.7 (5)
C17—C18—C19—C14−2.3 (8)C48—C47—C49—C50−175.9 (4)
C12—N4—C20—C22112.4 (5)C47—C49—C50—C51−55.5 (6)
C12—N4—C20—C21−121.3 (4)C47—C49—C50—C52−178.9 (4)
C29—N5—C21—O47.2 (7)C48—N9—C53—C55113.3 (5)
C29—N5—C21—C20−173.8 (4)C48—N9—C53—C54−123.7 (5)
N4—C20—C21—O4−122.1 (5)C4—N1—C54—O96.4 (7)
C22—C20—C21—O43.3 (6)C1—N1—C54—O9174.2 (5)
N4—C20—C21—N558.9 (5)C4—N1—C54—C53−169.4 (4)
C22—C20—C21—N5−175.8 (4)C1—N1—C54—C53−1.6 (7)
N4—C20—C22—C23−60.5 (5)N9—C53—C54—O9−88.4 (5)
C21—C20—C22—C23175.7 (4)C55—C53—C54—O932.6 (6)
C20—C22—C23—C2496.4 (5)N9—C53—C54—N187.5 (5)
C20—C22—C23—C28−77.0 (5)C55—C53—C54—N1−151.5 (4)
C28—C23—C24—C250.0 (7)N9—C53—C55—C57169.1 (4)
C22—C23—C24—C25−173.6 (4)C54—C53—C55—C5751.6 (6)
C23—C24—C25—C260.9 (8)N9—C53—C55—C56−67.9 (5)
C24—C25—C26—C27−2.0 (8)C54—C53—C55—C56174.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O90.882.082.834 (5)144
N7—H7···O40.882.303.112 (5)153
N8—H8···O50.882.122.985 (5)168
N9—H9N···O40.882.233.058 (5)157
N3—H3···N1S0.882.313.136 (7)157
C13—H13A···N1S0.992.673.451 (7)136
N5—H5···O8i0.882.603.103 (5)117
N6—H6···O8i0.882.423.153 (5)141
C1—H1A···O3ii0.992.483.378 (7)150
C31—H31B···O8i0.992.633.435 (6)139
C37—H37···O7i1.002.173.041 (6)145
C53—H53···O3ii1.002.353.187 (6)140
C2S—H2S1···O6iii0.982.373.268 (7)152
C4S—H4S1···O50.982.553.463 (9)155
C4S—H4S2···O60.982.623.246 (9)122
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+3/2, −y+1, z−1/2.
 

Acknowledgements

The authors acknowledge the kind contribution of [1–9-NαC]-linusorb B3 from Prairie Tide Chemicals Inc. (Saskatchewan, Canada), and the assistance of Dr Youn Young Shim (University of Saskatchewan) with proof-reading this article. We are also grateful to the Natural Sciences and Engineering Research Council of Canada (NSERC) and the Saskatchewan Ministry of Agriculture, through the Agricultural Development Fund (grant Nos. 20080205, 20120099 and 20120146), for financial support.

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2414-3146
Volume 1| Part 11| November 2016| x161706
https://doi.org/10.1107/S2414314616017065
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