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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1913–o1914.
Published online 2009 July 18. doi:  10.1107/S1600536809026841
PMCID: PMC2977324

Cyclo­linopeptide A methanol solvate

Abstract

Crystals of the title compound, C57H85N9O9·CH4O, the methanol solvate of a nine peptide polypeptide, cyclo-(Pro-Pro-Phe-Phe-Leu-Ile-Ile-Leu-Val), were obtained after separation of the cyclic peptide from flax oil. The cyclo­linopeptide A (CLP-A) mol­ecules are linked in chains along the a axis by N—H(...)O hydrogen bonds. Each methanol O atom is hydrogen bonded to one O atom and two N—H groups in the same CLP-A mol­ecule. There are a total of eight hydrogen bonds in each CLP-A–MeOH unit.

Related literature

For the isolation of CLP-A, see: Kaufmann & Tobschirbel (1959 [triangle]). For its synthesis and absolute configuration, see: Prox & Weygand (1966 [triangle]). For the crystal structure of the 2-propanol solvate, see: Di Blasio et al. (1989 [triangle]). For NMR studies and the crystal structure of a solvate of unstated composition of CLP-A, see: Matsumoto et al. (2002 [triangle]). For the cytoprotective ability of CLP-A, see: Kessler et al. (1986 [triangle]).

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Object name is e-65-o1913-scheme1.jpg

Experimental

Crystal data

  • C57H85N9O9·CH4O
  • M r = 1072.38
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1913-efi1.jpg
  • a = 9.8650 (4) Å
  • b = 22.6135 (5) Å
  • c = 26.5723 (10) Å
  • V = 5927.8 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 K
  • 0.20 × 0.05 × 0.05 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: none
  • 10352 measured reflections
  • 5817 independent reflections
  • 3987 reflections with I > 2σ(I)
  • R int = 0.070

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.110
  • S = 1.04
  • 5817 reflections
  • 707 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: COLLECT (Nonius, 1998 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026841/pv2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026841/pv2179Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial assistance for this project was provided by the Natural Sciences and Engineering Research Council of Canada. This work was also supported by a grant to MJTR from the Saskatchewan Agricultural Development Fund.

supplementary crystallographic information

Experimental

The title compound was extracted from flax oil by successive elution of a mixture of 700 ml of flax oil and 700 ml of 5% ethyl acetate in hexane. Fractions containing several cyclicpeptides were collected and dried by rotary evaporation. Further separation was achieved by using HPLC and acetonitrile/water solvent gradient. Each cyclicpeptide fraction was collectedand identified by NMR and MS. CLP-A was crystallized by dissolving it in minimum amount of methanol and then adding a few drops of water to the solution. After two days of slow evaporation of the methanol at room temperature, suitable crystals were harvested for crystallographic studies.

Refinement

H atoms bonded to N atoms were located in a difference map and then positioned geometrically with Uiso constrained to be 1.2 times Ueq(N).and the bond length constrained to 0.88 Å. Other H atoms were positioned geometrically and refined using a riding model (including free rotation for methyl groups with C—H = 0.95–0.99 Å and with Uiso(H) = 1.2(1.5 for methyl groups) times Ueq(C).

The chirality of the amino acids can not be determined from the anomalous dispersion, but the relative chirality is clearly all the same. The structure has no atom with Z>8. With Mo radiation and low resolution data, it is impossible to determine the absolute chirality from these data. Based on the synthesis of the molecule by Prox & Weygand (1966), we have assumed that all amino acids are S. All Friedel mates (4536) were merged in the refinement.

Figures

Fig. 1.
The stereo molecular structure of the title compound, with atom labels and 20% probability displacement ellipsoids for non-H atoms. Only H atoms on N or O atoms are included. The methanol molecule (C58—O10) has the C atom pointing toward the viewer. ...

Crystal data

C57H85N9O9·CH4OF(000) = 2320
Mr = 1072.38Dx = 1.202 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5719 reflections
a = 9.8650 (4) Åθ = 1.0–25.0°
b = 22.6135 (5) ŵ = 0.08 mm1
c = 26.5723 (10) ÅT = 173 K
V = 5927.8 (4) Å3Rod, colourless
Z = 40.20 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer3987 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.070
horizonally mounted graphite crystalθmax = 25.0°, θmin = 2.5°
Detector resolution: 9 pixels mm-1h = −11→11
[var phi] scans and ω scans with κ offsetsk = −26→26
10352 measured reflectionsl = −31→31
5817 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055w = 1/[σ2(Fo2) + (0.0289P)2 + 2.503P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.18 e Å3
5817 reflectionsΔρmin = −0.18 e Å3
707 parametersExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0040 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: syn
Secondary atom site location: difference Fourier map

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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)

xyzUiso*/Ueq
O10.6490 (4)0.14168 (15)0.41141 (12)0.0430 (9)
O21.1761 (4)0.24064 (13)0.42479 (13)0.0478 (9)
O31.3224 (3)0.14204 (15)0.30740 (11)0.0416 (8)
O40.9549 (3)0.15024 (13)0.20281 (11)0.0347 (8)
O51.0026 (3)0.27819 (12)0.13135 (10)0.0339 (8)
O61.0140 (4)0.20528 (15)0.00902 (12)0.0473 (9)
O70.6008 (3)0.14060 (13)0.09504 (11)0.0378 (8)
O80.4485 (3)0.20492 (14)0.19539 (12)0.0396 (8)
O90.8048 (3)0.11313 (13)0.31070 (11)0.0366 (8)
N10.6840 (4)0.19658 (15)0.32071 (13)0.0315 (9)
N20.8407 (4)0.17833 (15)0.44576 (13)0.0326 (9)
N31.0975 (4)0.14799 (15)0.40928 (13)0.0301 (9)
H31.02700.12420.41050.036*
N41.1175 (4)0.09880 (15)0.30765 (13)0.0311 (9)
H41.04870.08650.32600.037*
N51.1410 (4)0.19582 (14)0.23273 (12)0.0293 (9)
H51.21810.19280.24920.035*
N61.1765 (4)0.21291 (14)0.12955 (12)0.0306 (9)
H61.23360.19160.14740.037*
N70.9621 (4)0.15497 (15)0.08001 (13)0.0297 (9)
H70.99070.14310.10970.036*
N80.7432 (4)0.21286 (14)0.11963 (13)0.0300 (9)
H80.82670.22660.11980.036*
N90.6568 (4)0.16721 (15)0.21162 (13)0.0303 (9)
H90.74240.16680.20220.036*
C10.7682 (5)0.21527 (17)0.36348 (15)0.0317 (11)
H10.86610.21660.35380.038*
C20.7145 (5)0.27780 (19)0.37430 (18)0.0396 (12)
H2A0.72170.28730.41060.047*
H2B0.76530.30780.35480.047*
C30.5667 (5)0.2754 (2)0.35773 (18)0.0413 (13)
H3A0.50920.25660.38380.050*
H3B0.53130.31540.35040.050*
C40.5729 (5)0.23786 (19)0.31047 (17)0.0349 (12)
H4A0.48650.21650.30500.042*
H4B0.59260.26240.28050.042*
C50.7468 (5)0.17461 (19)0.40867 (17)0.0329 (11)
C60.9504 (5)0.22168 (18)0.45025 (16)0.0318 (11)
H6A0.92020.26010.43540.038*
C70.9657 (6)0.2288 (2)0.50758 (17)0.0472 (14)
H7A1.05960.23990.51670.057*
H7B0.90250.25910.52080.057*
C80.9302 (6)0.1678 (2)0.52744 (18)0.0493 (15)
H8A1.00900.14080.52500.059*
H8B0.90050.16990.56300.059*
C90.8159 (6)0.1470 (2)0.49388 (16)0.0444 (13)
H9A0.81900.10360.48920.053*
H9B0.72670.15800.50820.053*
C101.0851 (5)0.20366 (19)0.42662 (16)0.0322 (11)
C111.2247 (5)0.12615 (18)0.38849 (15)0.0297 (11)
H111.29660.15520.39820.036*
C121.2646 (5)0.06659 (18)0.41182 (16)0.0349 (12)
H12A1.19280.03720.40470.042*
H12B1.34960.05250.39600.042*
C131.2848 (5)0.07110 (18)0.46802 (16)0.0333 (11)
C141.3965 (6)0.1017 (2)0.48615 (18)0.0409 (13)
H141.45960.11860.46330.049*
C151.4166 (6)0.1079 (2)0.53792 (19)0.0485 (14)
H151.49200.12980.55000.058*
C161.3284 (7)0.0826 (2)0.5714 (2)0.0557 (17)
H161.34330.08620.60650.067*
C171.2180 (7)0.0521 (2)0.5536 (2)0.0598 (17)
H171.15560.03490.57650.072*
C181.1972 (6)0.0460 (2)0.5022 (2)0.0485 (14)
H181.12120.02430.49040.058*
C191.2238 (5)0.12317 (19)0.33097 (16)0.0314 (11)
C201.1107 (5)0.09171 (17)0.25296 (15)0.0269 (10)
H201.20490.08420.24060.032*
C211.0242 (5)0.03878 (16)0.23827 (17)0.0329 (11)
H21A0.93980.03920.25840.039*
H21B0.99860.04240.20240.039*
C221.0956 (5)−0.01974 (17)0.24623 (16)0.0298 (11)
C401.0429 (5)0.18986 (18)0.05201 (17)0.0326 (11)
C231.0602 (6)−0.0571 (2)0.28522 (18)0.0439 (13)
H230.9903−0.04620.30800.053*
C241.1268 (6)−0.1108 (2)0.2911 (2)0.0524 (15)
H241.1013−0.13660.31770.063*
C251.2290 (6)−0.1269 (2)0.2589 (2)0.0529 (15)
H251.2744−0.16360.26330.064*
C261.2657 (6)−0.0897 (2)0.2200 (2)0.0483 (14)
H261.3366−0.10060.19760.058*
C271.1989 (5)−0.03658 (19)0.21373 (17)0.0380 (12)
H271.2239−0.01120.18680.046*
C281.0596 (5)0.14826 (19)0.22772 (15)0.0284 (11)
C291.1011 (5)0.25230 (17)0.21081 (15)0.0279 (11)
H291.00960.26270.22440.033*
C301.1993 (5)0.30132 (18)0.22619 (15)0.0323 (11)
H30A1.16690.33890.21130.039*
H30B1.28880.29250.21110.039*
C311.2193 (5)0.31099 (18)0.28272 (16)0.0348 (12)
H311.26660.27550.29680.042*
C321.3105 (6)0.3640 (2)0.28986 (19)0.0497 (14)
H32A1.39690.35720.27260.075*
H32B1.32710.37010.32590.075*
H32C1.26670.39920.27570.075*
C331.0869 (6)0.3191 (2)0.31117 (18)0.0483 (14)
H33A1.10610.32470.34700.072*
H33B1.03020.28380.30680.072*
H33C1.03910.35380.29810.072*
C341.0895 (5)0.24901 (18)0.15363 (16)0.0279 (11)
C351.1790 (5)0.20796 (19)0.07441 (15)0.0327 (11)
H351.20180.24790.06070.039*
C361.2942 (5)0.16549 (19)0.05862 (17)0.0380 (12)
H361.37960.18160.07360.046*
C371.2770 (6)0.1035 (2)0.0797 (2)0.0570 (16)
H37A1.25460.10580.11550.085*
H37B1.36170.08130.07540.085*
H37C1.20380.08320.06170.085*
C381.3130 (6)0.1670 (2)0.00099 (18)0.0566 (16)
H38A1.23240.1490−0.01500.068*
H38B1.31760.2088−0.01010.068*
C391.4375 (6)0.1354 (3)−0.0172 (2)0.0685 (18)
H39A1.51830.1544−0.00310.103*
H39B1.44130.1372−0.05400.103*
H39C1.43410.0940−0.00640.103*
C410.8284 (5)0.13627 (18)0.06258 (16)0.0302 (11)
H410.81800.15220.02770.036*
C420.8155 (5)0.06915 (17)0.05847 (16)0.0334 (11)
H420.71870.06000.05040.040*
C430.9024 (6)0.04506 (19)0.01514 (17)0.0432 (13)
H43A0.87370.0634−0.01650.065*
H43B0.89090.00210.01290.065*
H43C0.99790.05430.02140.065*
C440.8494 (6)0.03857 (19)0.10812 (17)0.0430 (13)
H44A0.81010.06190.13610.052*
H44B0.94900.03830.11250.052*
C450.7974 (7)−0.0249 (2)0.1119 (2)0.0662 (19)
H45A0.6985−0.02510.10830.099*
H45B0.8222−0.04140.14470.099*
H45C0.8381−0.04880.08510.099*
C460.7138 (5)0.16320 (19)0.09380 (16)0.0293 (11)
C470.6373 (5)0.24396 (18)0.14739 (16)0.0296 (11)
H470.68520.27510.16740.036*
C480.5339 (5)0.27708 (18)0.11482 (17)0.0349 (12)
H48A0.56870.27890.07990.042*
H48B0.44850.25410.11420.042*
C490.5025 (5)0.33970 (18)0.13241 (17)0.0381 (12)
H490.49570.33950.17000.046*
C500.6146 (6)0.3831 (2)0.1172 (2)0.0574 (16)
H50A0.61240.38910.08070.086*
H50B0.70300.36700.12700.086*
H50C0.60010.42100.13420.086*
C510.3655 (6)0.3595 (2)0.1108 (2)0.0532 (15)
H51A0.36890.35810.07400.080*
H51B0.34620.40010.12170.080*
H51C0.29390.33310.12300.080*
C520.5702 (5)0.20273 (19)0.18643 (16)0.0318 (11)
C530.6163 (5)0.12948 (18)0.25350 (15)0.0299 (11)
H530.52140.14030.26300.036*
C540.6182 (5)0.06326 (19)0.24054 (16)0.0352 (12)
H540.71310.05130.23210.042*
C550.5690 (6)0.0265 (2)0.28561 (19)0.0494 (14)
H55A0.47570.03770.29400.074*
H55B0.62780.03390.31460.074*
H55C0.5720−0.01560.27700.074*
C560.5271 (5)0.05127 (19)0.19503 (17)0.0418 (13)
H56A0.53410.00950.18550.063*
H56B0.55600.07610.16680.063*
H56C0.43290.06050.20370.063*
C570.7083 (5)0.14515 (19)0.29755 (15)0.0316 (11)
O100.9112 (4)0.05125 (13)0.38798 (13)0.0459 (9)
H100.85680.06750.36800.069*
C580.8484 (7)0.0016 (2)0.4104 (2)0.077 (2)
H58A0.9140−0.01900.43180.115*
H58B0.8163−0.02530.38400.115*
H58C0.77140.01470.43090.115*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.036 (2)0.056 (2)0.0375 (19)−0.0097 (19)0.0011 (17)0.0004 (17)
O20.039 (2)0.0397 (18)0.065 (2)−0.0085 (18)0.000 (2)−0.0096 (17)
O30.028 (2)0.065 (2)0.0321 (18)−0.0092 (18)0.0015 (17)−0.0004 (16)
O40.025 (2)0.0398 (17)0.0397 (18)−0.0002 (15)−0.0053 (16)0.0026 (15)
O50.035 (2)0.0353 (16)0.0312 (17)0.0046 (16)−0.0063 (16)0.0005 (14)
O60.036 (2)0.074 (2)0.0314 (19)−0.009 (2)−0.0023 (17)0.0084 (17)
O70.027 (2)0.0432 (18)0.043 (2)0.0017 (17)−0.0029 (17)−0.0028 (16)
O80.024 (2)0.0544 (19)0.0400 (19)0.0091 (17)−0.0007 (16)0.0018 (16)
O90.033 (2)0.0461 (18)0.0306 (18)0.0125 (17)−0.0018 (16)0.0001 (15)
N10.027 (2)0.040 (2)0.027 (2)0.0016 (19)−0.0005 (18)−0.0023 (17)
N20.027 (2)0.042 (2)0.029 (2)−0.0045 (19)−0.0007 (19)0.0025 (17)
N30.027 (2)0.0294 (19)0.034 (2)−0.0047 (17)−0.0002 (18)−0.0032 (17)
N40.028 (2)0.039 (2)0.027 (2)−0.0071 (18)−0.0003 (19)−0.0032 (17)
N50.027 (2)0.0325 (19)0.028 (2)0.0026 (18)−0.0056 (18)−0.0006 (16)
N60.031 (2)0.032 (2)0.029 (2)0.0040 (18)−0.0012 (18)−0.0013 (16)
N70.028 (2)0.034 (2)0.027 (2)0.0058 (18)−0.0013 (18)0.0046 (16)
N80.022 (2)0.036 (2)0.032 (2)0.0002 (18)−0.0001 (17)−0.0021 (17)
N90.023 (2)0.043 (2)0.025 (2)0.0054 (18)0.0006 (17)−0.0012 (17)
C10.024 (3)0.040 (2)0.031 (2)0.000 (2)−0.005 (2)0.001 (2)
C20.042 (3)0.043 (3)0.035 (3)0.004 (3)−0.004 (2)−0.002 (2)
C30.038 (3)0.043 (3)0.043 (3)0.008 (2)0.000 (3)−0.004 (2)
C40.027 (3)0.040 (2)0.037 (3)0.010 (2)−0.001 (2)−0.003 (2)
C50.028 (3)0.038 (3)0.032 (3)0.001 (2)−0.001 (2)−0.004 (2)
C60.027 (3)0.032 (2)0.036 (3)0.000 (2)−0.004 (2)−0.004 (2)
C70.049 (4)0.059 (3)0.033 (3)0.001 (3)−0.004 (3)−0.011 (2)
C80.059 (4)0.059 (3)0.030 (3)0.005 (3)−0.007 (3)−0.005 (2)
C90.054 (4)0.049 (3)0.029 (3)0.000 (3)0.001 (3)0.007 (2)
C100.034 (3)0.033 (2)0.031 (2)−0.006 (2)−0.005 (2)−0.005 (2)
C110.022 (3)0.037 (2)0.030 (2)0.000 (2)−0.002 (2)0.003 (2)
C120.032 (3)0.036 (2)0.037 (3)0.004 (2)0.001 (2)0.003 (2)
C130.031 (3)0.037 (2)0.032 (3)0.006 (2)−0.002 (2)0.005 (2)
C140.035 (3)0.051 (3)0.037 (3)0.007 (3)0.001 (3)0.007 (2)
C150.055 (4)0.048 (3)0.043 (3)0.009 (3)−0.008 (3)−0.002 (2)
C160.088 (5)0.042 (3)0.037 (3)0.017 (3)0.001 (3)0.001 (3)
C170.087 (5)0.047 (3)0.045 (3)0.010 (3)0.023 (4)0.016 (3)
C180.046 (4)0.042 (3)0.057 (4)−0.001 (3)0.003 (3)0.009 (3)
C190.028 (3)0.035 (2)0.031 (3)0.003 (2)0.000 (2)0.003 (2)
C200.020 (3)0.034 (2)0.027 (2)0.000 (2)0.001 (2)−0.0012 (19)
C210.031 (3)0.032 (2)0.035 (3)0.004 (2)−0.004 (2)−0.003 (2)
C220.032 (3)0.028 (2)0.029 (2)−0.002 (2)−0.008 (2)−0.004 (2)
C400.030 (3)0.036 (2)0.032 (3)0.001 (2)0.000 (2)0.001 (2)
C230.048 (4)0.048 (3)0.036 (3)−0.007 (3)−0.005 (3)0.002 (2)
C240.059 (4)0.043 (3)0.054 (4)−0.009 (3)−0.015 (3)0.015 (3)
C250.056 (4)0.035 (3)0.068 (4)0.005 (3)−0.015 (3)0.000 (3)
C260.049 (4)0.042 (3)0.054 (3)0.008 (3)−0.002 (3)−0.011 (3)
C270.043 (3)0.037 (2)0.034 (3)0.003 (2)−0.004 (3)−0.001 (2)
C280.027 (3)0.034 (2)0.025 (2)0.006 (2)0.000 (2)−0.0059 (19)
C290.027 (3)0.026 (2)0.030 (2)0.005 (2)−0.002 (2)−0.0034 (19)
C300.034 (3)0.033 (2)0.030 (2)0.001 (2)0.002 (2)−0.002 (2)
C310.035 (3)0.035 (2)0.035 (3)0.007 (2)−0.006 (2)−0.001 (2)
C320.046 (4)0.049 (3)0.054 (3)0.000 (3)−0.009 (3)−0.018 (3)
C330.047 (4)0.062 (3)0.035 (3)0.003 (3)0.003 (3)−0.008 (2)
C340.024 (3)0.029 (2)0.031 (2)−0.005 (2)−0.004 (2)−0.003 (2)
C350.034 (3)0.037 (2)0.027 (2)0.001 (2)0.011 (2)−0.005 (2)
C360.031 (3)0.045 (3)0.038 (3)0.002 (2)−0.003 (2)−0.010 (2)
C370.044 (4)0.045 (3)0.082 (4)0.010 (3)0.004 (3)−0.002 (3)
C380.052 (4)0.078 (4)0.040 (3)0.015 (3)0.000 (3)−0.017 (3)
C390.058 (4)0.098 (4)0.050 (4)0.013 (4)0.006 (3)−0.014 (3)
C410.024 (3)0.036 (2)0.031 (2)0.002 (2)−0.004 (2)−0.001 (2)
C420.031 (3)0.034 (2)0.035 (3)−0.001 (2)−0.003 (2)−0.003 (2)
C430.049 (4)0.038 (3)0.042 (3)0.007 (3)0.005 (3)−0.006 (2)
C440.048 (4)0.039 (3)0.042 (3)0.005 (3)0.003 (3)0.006 (2)
C450.082 (5)0.047 (3)0.070 (4)0.001 (3)0.025 (4)0.005 (3)
C460.024 (3)0.038 (3)0.027 (2)0.003 (2)−0.005 (2)0.002 (2)
C470.025 (3)0.031 (2)0.033 (2)0.008 (2)−0.001 (2)−0.004 (2)
C480.032 (3)0.036 (2)0.036 (3)0.009 (2)−0.006 (2)0.003 (2)
C490.044 (3)0.037 (2)0.033 (3)0.004 (2)−0.001 (3)0.002 (2)
C500.065 (4)0.049 (3)0.059 (4)−0.009 (3)−0.006 (3)0.010 (3)
C510.053 (4)0.052 (3)0.054 (3)0.022 (3)0.002 (3)0.008 (3)
C520.031 (3)0.037 (2)0.027 (2)0.007 (2)−0.003 (2)−0.008 (2)
C530.025 (3)0.041 (2)0.024 (2)0.004 (2)−0.001 (2)−0.003 (2)
C540.028 (3)0.045 (3)0.032 (3)0.003 (2)−0.001 (2)−0.005 (2)
C550.056 (4)0.041 (3)0.051 (3)−0.005 (3)0.000 (3)0.006 (2)
C560.041 (3)0.042 (3)0.043 (3)−0.005 (3)0.000 (3)−0.005 (2)
C570.027 (3)0.043 (3)0.025 (2)0.001 (2)0.008 (2)0.002 (2)
O100.040 (2)0.0381 (18)0.060 (2)−0.0069 (17)−0.0121 (19)0.0105 (16)
C580.085 (5)0.062 (4)0.083 (5)−0.034 (4)−0.002 (4)0.017 (3)

Geometric parameters (Å, °)

O1—C51.221 (5)C23—H230.9500
O2—C101.228 (5)C24—C251.372 (8)
O3—C191.233 (5)C24—H240.9500
O4—C281.227 (5)C25—C261.381 (7)
O5—C341.233 (5)C25—H250.9500
O6—C401.228 (5)C26—C271.380 (6)
O7—C461.227 (5)C26—H260.9500
O8—C521.225 (6)C27—H270.9500
O9—C571.246 (5)C29—C341.526 (6)
N1—C571.337 (5)C29—C301.528 (6)
N1—C41.465 (5)C29—H291.0000
N1—C11.470 (5)C30—C311.531 (6)
N2—C51.355 (6)C30—H30A0.9900
N2—C61.465 (5)C30—H30B0.9900
N2—C91.482 (5)C31—C321.512 (6)
N3—C101.346 (5)C31—C331.520 (7)
N3—C111.457 (6)C31—H311.0000
N3—H30.8800C32—H32A0.9800
N4—C191.337 (6)C32—H32B0.9800
N4—C201.464 (5)C32—H32C0.9800
N4—H40.8800C33—H33A0.9800
N5—C281.349 (5)C33—H33B0.9800
N5—C291.458 (5)C33—H33C0.9800
N5—H50.8800C35—C361.546 (6)
N6—C341.346 (5)C35—H351.0000
N6—C351.470 (5)C36—C371.520 (6)
N6—H60.8800C36—C381.543 (6)
N7—C401.346 (6)C36—H361.0000
N7—C411.460 (6)C37—H37A0.9800
N7—H70.8800C37—H37B0.9800
N8—C461.348 (5)C37—H37C0.9800
N8—C471.459 (5)C38—C391.502 (8)
N8—H80.8800C38—H38A0.9900
N9—C521.350 (6)C38—H38B0.9900
N9—C531.458 (5)C39—H39A0.9800
N9—H90.8800C39—H39B0.9800
C1—C51.527 (6)C39—H39C0.9800
C1—C21.537 (6)C41—C421.527 (6)
C1—H11.0000C41—C461.529 (6)
C2—C31.524 (7)C41—H411.0000
C2—H2A0.9900C42—C441.526 (6)
C2—H2B0.9900C42—C431.535 (6)
C3—C41.517 (6)C42—H421.0000
C3—H3A0.9900C43—H43A0.9800
C3—H3B0.9900C43—H43B0.9800
C4—H4A0.9900C43—H43C0.9800
C4—H4B0.9900C44—C451.527 (6)
C6—C101.525 (6)C44—H44A0.9900
C6—C71.539 (6)C44—H44B0.9900
C6—H6A1.0000C45—H45A0.9800
C7—C81.519 (6)C45—H45B0.9800
C7—H7A0.9900C45—H45C0.9800
C7—H7B0.9900C47—C481.533 (6)
C8—C91.513 (7)C47—C521.544 (6)
C8—H8A0.9900C47—H471.0000
C8—H8B0.9900C48—C491.523 (6)
C9—H9A0.9900C48—H48A0.9900
C9—H9B0.9900C48—H48B0.9900
C11—C191.530 (6)C49—C501.533 (7)
C11—C121.534 (6)C49—C511.535 (7)
C11—H111.0000C49—H491.0000
C12—C131.510 (6)C50—H50A0.9800
C12—H12A0.9900C50—H50B0.9800
C12—H12B0.9900C50—H50C0.9800
C13—C181.376 (7)C51—H51A0.9800
C13—C141.388 (7)C51—H51B0.9800
C14—C151.397 (7)C51—H51C0.9800
C14—H140.9500C53—C571.523 (6)
C15—C161.369 (8)C53—C541.537 (6)
C15—H150.9500C53—H531.0000
C16—C171.374 (8)C54—C561.531 (6)
C16—H160.9500C54—C551.537 (6)
C17—C181.386 (7)C54—H541.0000
C17—H170.9500C55—H55A0.9800
C18—H180.9500C55—H55B0.9800
C20—C211.521 (6)C55—H55C0.9800
C20—C281.530 (6)C56—H56A0.9800
C20—H201.0000C56—H56B0.9800
C21—C221.514 (6)C56—H56C0.9800
C21—H21A0.9900O10—C581.414 (6)
C21—H21B0.9900O10—H100.8400
C22—C231.383 (6)C58—H58A0.9800
C22—C271.388 (6)C58—H58B0.9800
C40—C351.525 (7)C58—H58C0.9800
C23—C241.389 (7)
C57—N1—C4127.1 (4)C29—C30—H30A108.1
C57—N1—C1120.3 (4)C31—C30—H30A108.1
C4—N1—C1112.5 (3)C29—C30—H30B108.1
C5—N2—C6127.3 (4)C31—C30—H30B108.1
C5—N2—C9119.0 (4)H30A—C30—H30B107.3
C6—N2—C9111.8 (4)C32—C31—C33110.7 (4)
C10—N3—C11121.7 (4)C32—C31—C30108.3 (4)
C10—N3—H3119.2C33—C31—C30113.2 (4)
C11—N3—H3119.2C32—C31—H31108.2
C19—N4—C20122.7 (4)C33—C31—H31108.2
C19—N4—H4118.6C30—C31—H31108.2
C20—N4—H4118.6C31—C32—H32A109.5
C28—N5—C29119.9 (4)C31—C32—H32B109.5
C28—N5—H5120.1H32A—C32—H32B109.5
C29—N5—H5120.1C31—C32—H32C109.5
C34—N6—C35122.1 (4)H32A—C32—H32C109.5
C34—N6—H6119.0H32B—C32—H32C109.5
C35—N6—H6119.0C31—C33—H33A109.5
C40—N7—C41121.9 (4)C31—C33—H33B109.5
C40—N7—H7119.0H33A—C33—H33B109.5
C41—N7—H7119.0C31—C33—H33C109.5
C46—N8—C47120.3 (4)H33A—C33—H33C109.5
C46—N8—H8119.8H33B—C33—H33C109.5
C47—N8—H8119.8O5—C34—N6122.6 (4)
C52—N9—C53123.5 (4)O5—C34—C29120.3 (4)
C52—N9—H9118.2N6—C34—C29117.1 (4)
C53—N9—H9118.2N6—C35—C40113.2 (4)
N1—C1—C5110.9 (4)N6—C35—C36109.3 (4)
N1—C1—C2102.4 (3)C40—C35—C36112.0 (3)
C5—C1—C2111.0 (4)N6—C35—H35107.3
N1—C1—H1110.8C40—C35—H35107.3
C5—C1—H1110.8C36—C35—H35107.3
C2—C1—H1110.8C37—C36—C38113.5 (4)
C3—C2—C1104.1 (4)C37—C36—C35113.1 (4)
C3—C2—H2A110.9C38—C36—C35110.1 (4)
C1—C2—H2A110.9C37—C36—H36106.5
C3—C2—H2B110.9C38—C36—H36106.5
C1—C2—H2B110.9C35—C36—H36106.5
H2A—C2—H2B109.0C36—C37—H37A109.5
C4—C3—C2102.8 (4)C36—C37—H37B109.5
C4—C3—H3A111.2H37A—C37—H37B109.5
C2—C3—H3A111.2C36—C37—H37C109.5
C4—C3—H3B111.2H37A—C37—H37C109.5
C2—C3—H3B111.2H37B—C37—H37C109.5
H3A—C3—H3B109.1C39—C38—C36114.0 (5)
N1—C4—C3103.5 (4)C39—C38—H38A108.7
N1—C4—H4A111.1C36—C38—H38A108.7
C3—C4—H4A111.1C39—C38—H38B108.7
N1—C4—H4B111.1C36—C38—H38B108.7
C3—C4—H4B111.1H38A—C38—H38B107.6
H4A—C4—H4B109.0C38—C39—H39A109.5
O1—C5—N2122.3 (4)C38—C39—H39B109.5
O1—C5—C1121.6 (4)H39A—C39—H39B109.5
N2—C5—C1116.1 (4)C38—C39—H39C109.5
N2—C6—C10115.6 (3)H39A—C39—H39C109.5
N2—C6—C7102.9 (4)H39B—C39—H39C109.5
C10—C6—C7110.5 (4)N7—C41—C42112.7 (4)
N2—C6—H6A109.2N7—C41—C46112.4 (3)
C10—C6—H6A109.2C42—C41—C46111.9 (4)
C7—C6—H6A109.2N7—C41—H41106.4
C8—C7—C6103.1 (4)C42—C41—H41106.4
C8—C7—H7A111.2C46—C41—H41106.4
C6—C7—H7A111.2C44—C42—C41111.7 (3)
C8—C7—H7B111.2C44—C42—C43111.4 (4)
C6—C7—H7B111.2C41—C42—C43111.1 (4)
H7A—C7—H7B109.1C44—C42—H42107.4
C9—C8—C7104.4 (4)C41—C42—H42107.4
C9—C8—H8A110.9C43—C42—H42107.4
C7—C8—H8A110.9C42—C43—H43A109.5
C9—C8—H8B110.9C42—C43—H43B109.5
C7—C8—H8B110.9H43A—C43—H43B109.5
H8A—C8—H8B108.9C42—C43—H43C109.5
N2—C9—C8103.7 (4)H43A—C43—H43C109.5
N2—C9—H9A111.0H43B—C43—H43C109.5
C8—C9—H9A111.0C42—C44—C45114.1 (4)
N2—C9—H9B111.0C42—C44—H44A108.7
C8—C9—H9B111.0C45—C44—H44A108.7
H9A—C9—H9B109.0C42—C44—H44B108.7
O2—C10—N3123.9 (4)C45—C44—H44B108.7
O2—C10—C6118.1 (4)H44A—C44—H44B107.6
N3—C10—C6118.0 (4)C44—C45—H45A109.5
N3—C11—C19112.9 (4)C44—C45—H45B109.5
N3—C11—C12111.4 (4)H45A—C45—H45B109.5
C19—C11—C12111.5 (4)C44—C45—H45C109.5
N3—C11—H11106.9H45A—C45—H45C109.5
C19—C11—H11106.9H45B—C45—H45C109.5
C12—C11—H11106.9O7—C46—N8121.9 (4)
C13—C12—C11112.0 (3)O7—C46—C41121.4 (4)
C13—C12—H12A109.2N8—C46—C41116.7 (4)
C11—C12—H12A109.2N8—C47—C48115.2 (4)
C13—C12—H12B109.2N8—C47—C52110.8 (3)
C11—C12—H12B109.2C48—C47—C52112.9 (4)
H12A—C12—H12B107.9N8—C47—H47105.7
C18—C13—C14118.3 (4)C48—C47—H47105.7
C18—C13—C12122.9 (5)C52—C47—H47105.7
C14—C13—C12118.8 (4)C49—C48—C47114.6 (4)
C13—C14—C15120.3 (5)C49—C48—H48A108.6
C13—C14—H14119.9C47—C48—H48A108.6
C15—C14—H14119.9C49—C48—H48B108.6
C16—C15—C14120.5 (6)C47—C48—H48B108.6
C16—C15—H15119.7H48A—C48—H48B107.6
C14—C15—H15119.7C48—C49—C50111.6 (4)
C15—C16—C17119.4 (5)C48—C49—C51109.6 (4)
C15—C16—H16120.3C50—C49—C51110.5 (4)
C17—C16—H16120.3C48—C49—H49108.4
C16—C17—C18120.4 (6)C50—C49—H49108.4
C16—C17—H17119.8C51—C49—H49108.4
C18—C17—H17119.8C49—C50—H50A109.5
C13—C18—C17121.1 (6)C49—C50—H50B109.5
C13—C18—H18119.4H50A—C50—H50B109.5
C17—C18—H18119.4C49—C50—H50C109.5
O3—C19—N4121.7 (4)H50A—C50—H50C109.5
O3—C19—C11119.2 (4)H50B—C50—H50C109.5
N4—C19—C11119.0 (4)C49—C51—H51A109.5
N4—C20—C21111.5 (4)C49—C51—H51B109.5
N4—C20—C28111.0 (3)H51A—C51—H51B109.5
C21—C20—C28111.1 (4)C49—C51—H51C109.5
N4—C20—H20107.7H51A—C51—H51C109.5
C21—C20—H20107.7H51B—C51—H51C109.5
C28—C20—H20107.7O8—C52—N9123.2 (5)
C22—C21—C20113.0 (4)O8—C52—C47121.8 (4)
C22—C21—H21A109.0N9—C52—C47114.9 (4)
C20—C21—H21A109.0N9—C53—C57106.7 (3)
C22—C21—H21B109.0N9—C53—C54113.3 (3)
C20—C21—H21B109.0C57—C53—C54113.0 (4)
H21A—C21—H21B107.8N9—C53—H53107.9
C23—C22—C27118.9 (4)C57—C53—H53107.9
C23—C22—C21121.4 (4)C54—C53—H53107.9
C27—C22—C21119.6 (4)C56—C54—C53110.0 (4)
O6—C40—N7122.9 (5)C56—C54—C55109.5 (4)
O6—C40—C35119.4 (4)C53—C54—C55110.4 (4)
N7—C40—C35117.6 (4)C56—C54—H54108.9
C22—C23—C24119.9 (5)C53—C54—H54108.9
C22—C23—H23120.0C55—C54—H54108.9
C24—C23—H23120.0C54—C55—H55A109.5
C25—C24—C23120.6 (5)C54—C55—H55B109.5
C25—C24—H24119.7H55A—C55—H55B109.5
C23—C24—H24119.7C54—C55—H55C109.5
C24—C25—C26119.9 (5)H55A—C55—H55C109.5
C24—C25—H25120.1H55B—C55—H55C109.5
C26—C25—H25120.1C54—C56—H56A109.5
C27—C26—C25119.7 (5)C54—C56—H56B109.5
C27—C26—H26120.2H56A—C56—H56B109.5
C25—C26—H26120.2C54—C56—H56C109.5
C26—C27—C22121.0 (5)H56A—C56—H56C109.5
C26—C27—H27119.5H56B—C56—H56C109.5
C22—C27—H27119.5O9—C57—N1120.9 (4)
O4—C28—N5121.7 (4)O9—C57—C53122.4 (4)
O4—C28—C20123.0 (4)N1—C57—C53116.7 (4)
N5—C28—C20115.3 (4)C58—O10—H10109.5
N5—C29—C34112.1 (3)O10—C58—H58A109.5
N5—C29—C30110.9 (4)O10—C58—H58B109.5
C34—C29—C30110.4 (3)H58A—C58—H58B109.5
N5—C29—H29107.7O10—C58—H58C109.5
C34—C29—H29107.7H58A—C58—H58C109.5
C30—C29—H29107.7H58B—C58—H58C109.5
C29—C30—C31116.6 (4)
C57—N1—C1—C5−66.9 (5)C29—N5—C28—O43.8 (6)
C4—N1—C1—C5109.6 (4)C29—N5—C28—C20−179.0 (3)
C57—N1—C1—C2174.6 (4)N4—C20—C28—O4−118.6 (4)
C4—N1—C1—C2−8.9 (5)C21—C20—C28—O46.1 (6)
N1—C1—C2—C329.3 (4)N4—C20—C28—N564.3 (5)
C5—C1—C2—C3−89.1 (5)C21—C20—C28—N5−171.0 (4)
C1—C2—C3—C4−38.9 (5)C28—N5—C29—C34−62.7 (5)
C57—N1—C4—C3161.1 (4)C28—N5—C29—C30173.4 (4)
C1—N1—C4—C3−15.1 (5)N5—C29—C30—C31−56.4 (5)
C2—C3—C4—N132.7 (5)C34—C29—C30—C31178.7 (4)
C6—N2—C5—O1−170.5 (4)C29—C30—C31—C32−175.6 (4)
C9—N2—C5—O1−7.6 (7)C29—C30—C31—C33−52.4 (5)
C6—N2—C5—C18.1 (6)C35—N6—C34—O53.3 (7)
C9—N2—C5—C1170.9 (4)C35—N6—C34—C29−177.3 (4)
N1—C1—C5—O1−16.6 (6)N5—C29—C34—O5145.4 (4)
C2—C1—C5—O196.5 (5)C30—C29—C34—O5−90.4 (5)
N1—C1—C5—N2164.8 (4)N5—C29—C34—N6−33.9 (6)
C2—C1—C5—N2−82.1 (5)C30—C29—C34—N690.3 (4)
C5—N2—C6—C10−91.5 (5)C34—N6—C35—C40−57.2 (5)
C9—N2—C6—C10104.6 (4)C34—N6—C35—C36177.2 (4)
C5—N2—C6—C7148.0 (4)O6—C40—C35—N6152.2 (4)
C9—N2—C6—C7−15.9 (5)N7—C40—C35—N6−30.8 (5)
N2—C6—C7—C832.5 (5)O6—C40—C35—C36−83.6 (5)
C10—C6—C7—C8−91.4 (5)N7—C40—C35—C3693.3 (5)
C6—C7—C8—C9−37.8 (5)N6—C35—C36—C3760.5 (5)
C5—N2—C9—C8−172.7 (4)C40—C35—C36—C37−65.8 (5)
C6—N2—C9—C8−7.3 (5)N6—C35—C36—C38−171.4 (4)
C7—C8—C9—N228.0 (5)C40—C35—C36—C3862.3 (5)
C11—N3—C10—O22.7 (7)C37—C36—C38—C39−62.0 (7)
C11—N3—C10—C6−176.8 (4)C35—C36—C38—C39170.1 (5)
N2—C6—C10—O2172.7 (4)C40—N7—C41—C42119.7 (4)
C7—C6—C10—O2−71.0 (5)C40—N7—C41—C46−112.7 (4)
N2—C6—C10—N3−7.7 (6)N7—C41—C42—C4455.7 (5)
C7—C6—C10—N3108.6 (4)C46—C41—C42—C44−72.1 (5)
C10—N3—C11—C19−103.2 (5)N7—C41—C42—C43−69.5 (5)
C10—N3—C11—C12130.5 (4)C46—C41—C42—C43162.8 (4)
N3—C11—C12—C13−60.8 (5)C41—C42—C44—C45161.9 (4)
C19—C11—C12—C13172.1 (4)C43—C42—C44—C45−73.2 (6)
C11—C12—C13—C18109.8 (5)C47—N8—C46—O7−4.4 (6)
C11—C12—C13—C14−70.3 (6)C47—N8—C46—C41175.4 (4)
C18—C13—C14—C15−1.6 (7)N7—C41—C46—O7−158.5 (4)
C12—C13—C14—C15178.5 (4)C42—C41—C46—O7−30.6 (6)
C13—C14—C15—C161.7 (7)N7—C41—C46—N821.7 (5)
C14—C15—C16—C17−1.3 (8)C42—C41—C46—N8149.6 (4)
C15—C16—C17—C181.0 (8)C46—N8—C47—C48−72.2 (5)
C14—C13—C18—C171.3 (7)C46—N8—C47—C5257.5 (5)
C12—C13—C18—C17−178.9 (5)N8—C47—C48—C49−134.0 (4)
C16—C17—C18—C13−1.0 (8)C52—C47—C48—C4997.3 (5)
C20—N4—C19—O31.1 (7)C47—C48—C49—C5078.3 (5)
C20—N4—C19—C11−177.2 (4)C47—C48—C49—C51−159.0 (4)
N3—C11—C19—O3134.6 (4)C53—N9—C52—O8−2.6 (7)
C12—C11—C19—O3−99.1 (5)C53—N9—C52—C47173.5 (3)
N3—C11—C19—N4−47.0 (5)N8—C47—C52—O8−142.7 (4)
C12—C11—C19—N479.3 (5)C48—C47—C52—O8−11.7 (6)
C19—N4—C20—C21151.1 (4)N8—C47—C52—N941.1 (5)
C19—N4—C20—C28−84.4 (5)C48—C47—C52—N9172.1 (4)
N4—C20—C21—C22−76.0 (5)C52—N9—C53—C57−125.3 (4)
C28—C20—C21—C22159.6 (4)C52—N9—C53—C54109.7 (5)
C20—C21—C22—C23106.8 (5)N9—C53—C54—C56−56.7 (5)
C20—C21—C22—C27−73.3 (5)C57—C53—C54—C56−178.2 (4)
C41—N7—C40—O6−4.6 (6)N9—C53—C54—C55−177.7 (4)
C41—N7—C40—C35178.5 (3)C57—C53—C54—C5560.8 (5)
C27—C22—C23—C24−0.6 (7)C4—N1—C57—O9−178.1 (4)
C21—C22—C23—C24179.3 (4)C1—N1—C57—O9−2.2 (6)
C22—C23—C24—C250.8 (8)C4—N1—C57—C534.3 (6)
C23—C24—C25—C26−0.4 (8)C1—N1—C57—C53−179.8 (4)
C24—C25—C26—C27−0.2 (8)N9—C53—C57—O9−103.7 (5)
C25—C26—C27—C220.4 (8)C54—C53—C57—O921.5 (6)
C23—C22—C27—C26−0.1 (7)N9—C53—C57—N173.9 (5)
C21—C22—C27—C26−179.9 (4)C54—C53—C57—N1−160.9 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O100.882.092.912 (5)154
N4—H4···O100.882.283.139 (5)166
N4—H4···O90.882.513.103 (5)125
N5—H5···O30.882.182.935 (5)143
N6—H6···O8i0.882.493.208 (5)139
N7—H7···O40.882.503.266 (5)145
N8—H8···O50.882.112.971 (5)165
N9—H9···O40.882.132.975 (5)161
O10—H10···O90.841.912.698 (4)156

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2179).

References

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