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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2056–o2057.
Published online 2010 July 17. doi:  10.1107/S1600536810027169
PMCID: PMC3007348

4,4′-Ethyl­enedipyridinium bis­(3,4,5-trihy­droxy­benzoate) sesquihydrate

Abstract

The asymmetric unit of the title compound, C12H14N2 2+·2C7H5O5 ·1.5H2O, contains two 4,4′-ethyl­enedipyridinium cations, four gallate anions and three water mol­ecules. In the 4,4′-ethyl­enedipyridinium cations, the dihedral angles between the pyridinium rings are 4.3 (3) and 18.6 (3)°. Extensive classical N—H(...)O and O—H(...)O hydrogen bonding and weak C—H(...)O hydrogen bonding and C—H(...)π inter­actions are present in the crystal structure. π–π stacking is also observed, the centroid–centroid separations between the benzene and pyridine rings being 3.611 (3), 3.448 (3) and 3.536 (3) Å.

Related literature

For related structures, see: Bebout & Pagola (2009 [triangle]); Li & Guo (2007 [triangle]); Okabe et al. (2001 [triangle]). For the biological activity of gallic acid (3,4,5-trihy­droxy­benzoic acid) and its derivatives, see: Fukumoto & Mazza (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2056-scheme1.jpg

Experimental

Crystal data

  • C12H14N2 2+·2C7H5O5 ·1.5H2O
  • M r = 551.50
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2056-efi1.jpg
  • a = 9.4445 (19) Å
  • b = 15.331 (3) Å
  • c = 18.307 (4) Å
  • α = 109.88 (3)°
  • β = 93.68 (3)°
  • γ = 92.90 (3)°
  • V = 2480.2 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 295 K
  • 0.32 × 0.30 × 0.22 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 [triangle]) T min = 0.928, T max = 1.016
  • 26683 measured reflections
  • 8520 independent reflections
  • 5004 reflections with I > 2σ(I)
  • R int = 0.104

Refinement

  • R[F 2 > 2σ(F 2)] = 0.099
  • wR(F 2) = 0.221
  • S = 1.35
  • 8520 reflections
  • 713 parameters
  • H-atom parameters constrained
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO (Otwinowski & Minor, 1997 [triangle]) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027169/xu2790sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027169/xu2790Isup2.hkl

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

Acknowledgments

This work was financial supported by Yuanpei University, Taiwan.

supplementary crystallographic information

Comment

Gallic acid, 3,4,5-trihydroxybenzoic acid, and derivatives have been found to be antitumor and antioxidative activities (Fukumoto & Mazza,2000). Their related structures have been reported (Okabe et al.,2001; Li & Guo, 2007; Bebout & Pagola, 2009).

The crystal structure of the hydrated proton-transfer compound of gallic acid with 4,4'-ethylenedipyridine, 2(C12 H14 N22+2), 4(C7 H5 O5-). 3(H2O), contains two 4,4'-ethylenedipyridinium cations, four gallate anions and three water molecules in the asymmetry unit (shown as Fig.1). In the two 4,4'-ethylenedipyridinium cations, the dihedral angles between the pyridyl rings are 4.3 (3) and 18.6 (3) °. Three gallate anions have intramolecular hydrogen bonding. The hydroxyl H atoms bound to O4, O9, O10 and O14 (donors) form intramolecular hydrogen bonds to O5, O10, O9 and O15 (acceptors), respectively. The 4,4'-ethylenedipyridinium cations is linked by N—H···O hydrogen bonds to adjacent gallate anions, forming linear hydrogen bonded chains parallel to [1 0 1]. The structure exhibits a three dimension hydrogen-bonding network by involving OH···O(carboxylate) interactions. Intermolecular N—H···O, O—H···O and C—H···O hydrogen bondings are observed in the crystal structure (shown as Table 1, Fig. 2).

On the other hand, π–π ring stacking interactions are between benzene and pyridinium rings with centroid-centroid distances in the range 3.446 (3)\sim 3.612 (3) Å, the shortest distance between Cg4(N4/C20—C24)···Cg5(C26—C31) is 3.446 (3)Å and dihedral angle between two rings is 3.6 (2)° [symmetry code: 1+X,Y,Z]. In addition, C—H···π interactions C4—H4···Cg6(C33—C38), C16—H16A···Cg8(C47—C52); full details and symmetry codes are given in Table 1) are also present.

Experimental

The gallic acid (171.0 mg, 1.0 mmol) and 4,4'-ethylenedipyridine (184 mg, 1.0 mmol) were dissolved in 20 ml e thanol-water(2:1), the solution was refluxed for 30 min. The filtered solution was transferred to a 25 ml tube after one week at room temperature and pale pink transparent crystals formed (yield 48.19%).

Refinement

Water H atoms were located in a difference Fourier map and refined with the distances constraints of O—H = 0.86 Å, Uiso(H) = 1.5Ueq(O). Other H atoms were positioned geometrically with O—H = 0.82, N—H = 0.86, C—H = 0.93 (aromatic) and 0.97 Å (methylene), and were refined using a riding model with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O).

Figures

Fig. 1.
View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
Fig. 2.
The molecular packing for the title compound. Hydrogen-bonding associations are shown as dotted lines.

Crystal data

C12H14N22+·2C7H5O5·1.5H2OZ = 4
Mr = 551.50F(000) = 1156
Triclinic, P1Dx = 1.477 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4445 (19) ÅCell parameters from 6466 reflections
b = 15.331 (3) Åθ = 2.0–25.4°
c = 18.307 (4) ŵ = 0.12 mm1
α = 109.88 (3)°T = 295 K
β = 93.68 (3)°Prism, pale pink
γ = 92.90 (3)°0.32 × 0.30 × 0.22 mm
V = 2480.2 (10) Å3

Data collection

Nonius KappaCCD diffractometer8520 independent reflections
Radiation source: fine-focus sealed tube5004 reflections with I > 2σ(I)
graphiteRint = 0.104
Detector resolution: 9 pixels mm-1θmax = 25.0°, θmin = 2.3°
ω/2θ scansh = −10→11
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)k = −18→18
Tmin = 0.928, Tmax = 1.016l = −21→21
26683 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.099H-atom parameters constrained
wR(F2) = 0.221w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
S = 1.35(Δ/σ)max < 0.001
8520 reflectionsΔρmax = 0.47 e Å3
713 parametersΔρmin = −0.34 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (11)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.0070 (4)0.1378 (3)−0.5346 (2)0.0429 (14)
N20.3616 (4)0.1056 (3)−0.0603 (2)0.0511 (16)
C10.1482 (5)0.1376 (4)−0.5309 (3)0.0588 (19)
C20.2202 (5)0.1285 (4)−0.4683 (3)0.059 (2)
C30.1489 (5)0.1181 (3)−0.4071 (3)0.0436 (17)
C40.0033 (5)0.1187 (4)−0.4146 (3)0.0528 (19)
C5−0.0657 (5)0.1285 (4)−0.4789 (3)0.0538 (19)
C60.2334 (6)0.1095 (5)−0.3369 (3)0.066 (2)
C70.1507 (6)0.1160 (4)−0.2694 (3)0.061 (2)
C80.2315 (5)0.1118 (3)−0.1966 (3)0.0478 (17)
C90.3767 (6)0.1152 (4)−0.1849 (3)0.063 (2)
C100.4416 (6)0.1120 (4)−0.1156 (3)0.062 (2)
C110.2211 (6)0.1015 (4)−0.0708 (3)0.058 (2)
C120.1541 (6)0.1044 (4)−0.1371 (3)0.0601 (19)
N30.4594 (5)0.3694 (3)−0.0725 (2)0.0559 (18)
N40.8108 (4)0.3965 (3)0.4206 (2)0.0424 (14)
C130.5989 (6)0.3883 (5)−0.0571 (3)0.070 (3)
C140.6672 (5)0.3919 (4)0.0115 (3)0.061 (2)
C150.5926 (5)0.3742 (3)0.0680 (3)0.0408 (17)
C160.4471 (5)0.3556 (4)0.0523 (3)0.0543 (19)
C170.3848 (5)0.3548 (4)−0.0184 (3)0.060 (2)
C180.6711 (5)0.3755 (4)0.1427 (2)0.0446 (19)
C190.5841 (5)0.3929 (4)0.2125 (3)0.0420 (17)
C200.6656 (5)0.3950 (3)0.2859 (2)0.0354 (16)
C210.8103 (5)0.3868 (3)0.2908 (3)0.0452 (17)
C220.8806 (5)0.3879 (3)0.3587 (3)0.0487 (17)
C230.6707 (5)0.4047 (3)0.4187 (3)0.0446 (17)
C240.5966 (5)0.4043 (3)0.3523 (3)0.0425 (17)
O1−0.3781 (4)0.6359 (3)0.2075 (2)0.0792 (16)
O2−0.1568 (4)0.6257 (3)0.1798 (2)0.0803 (16)
O30.0893 (3)0.6021 (2)0.43137 (17)0.0480 (13)
O4−0.1136 (3)0.6249 (2)0.52719 (17)0.0487 (11)
O5−0.3839 (3)0.6427 (3)0.48367 (18)0.0563 (14)
C25−0.2473 (5)0.6308 (3)0.2254 (3)0.0441 (17)
C26−0.2122 (5)0.6294 (3)0.3059 (2)0.0352 (16)
C27−0.0736 (5)0.6189 (3)0.3292 (2)0.0380 (17)
C28−0.0425 (4)0.6155 (3)0.4034 (2)0.0349 (16)
C29−0.1483 (5)0.6252 (3)0.4543 (2)0.0355 (16)
C30−0.2869 (5)0.6346 (3)0.4293 (2)0.0382 (17)
C31−0.3195 (5)0.6361 (3)0.3551 (2)0.0377 (16)
O60.4085 (3)0.7394 (2)0.45724 (16)0.0445 (11)
O70.2951 (3)0.6363 (2)0.35056 (17)0.0410 (11)
O80.1899 (3)0.8332 (2)0.17878 (17)0.0523 (11)
O90.3017 (4)1.0079 (2)0.26833 (18)0.0576 (14)
O100.4411 (3)1.0399 (2)0.41025 (17)0.0493 (11)
C320.3465 (5)0.7175 (3)0.3894 (3)0.0353 (17)
C330.3355 (4)0.7930 (3)0.3552 (2)0.0332 (14)
C340.2652 (4)0.7745 (3)0.2810 (2)0.0366 (17)
C350.2552 (5)0.8458 (3)0.2510 (2)0.0379 (17)
C360.3112 (5)0.9355 (3)0.2946 (3)0.0367 (17)
C370.3818 (5)0.9525 (3)0.3671 (2)0.0360 (17)
C380.3918 (4)0.8822 (3)0.3980 (2)0.0343 (14)
O110.4349 (4)0.1139 (3)0.07976 (17)0.0547 (13)
O120.6552 (4)0.1230 (3)0.0530 (2)0.0733 (16)
O130.9199 (3)0.1324 (2)0.31510 (17)0.0454 (11)
O140.7270 (3)0.1783 (2)0.41445 (16)0.0447 (11)
O150.4537 (3)0.2027 (2)0.37189 (15)0.0372 (10)
C390.5680 (5)0.1251 (3)0.0995 (3)0.0431 (17)
C400.6112 (5)0.1418 (3)0.1840 (2)0.0355 (16)
C410.7500 (5)0.1325 (3)0.2087 (2)0.0378 (16)
C420.7860 (4)0.1435 (3)0.2851 (3)0.0363 (16)
C430.6847 (5)0.1665 (3)0.3391 (2)0.0329 (16)
C440.5473 (4)0.1789 (3)0.3151 (2)0.0319 (16)
C450.5111 (5)0.1657 (3)0.2376 (2)0.0336 (16)
O160.2520 (3)0.3050 (2)0.33605 (17)0.0447 (11)
O170.1281 (3)0.1815 (2)0.25025 (18)0.0440 (11)
O18−0.0104 (4)0.2787 (2)0.01976 (17)0.0511 (11)
O190.0747 (4)0.4575 (2)0.06270 (17)0.0515 (11)
O200.2244 (4)0.5481 (2)0.20255 (17)0.0505 (11)
C460.1795 (5)0.2653 (3)0.2719 (3)0.0340 (17)
C470.1545 (4)0.3173 (3)0.2172 (2)0.0304 (14)
C480.0839 (4)0.2722 (3)0.1439 (2)0.0366 (16)
C490.0586 (4)0.3185 (3)0.0922 (2)0.0353 (16)
C500.1037 (5)0.4130 (3)0.1146 (2)0.0373 (17)
C510.1760 (5)0.4580 (3)0.1875 (3)0.0366 (17)
C520.2004 (4)0.4110 (3)0.2388 (2)0.0339 (16)
O210.0657 (3)0.6585 (2)0.10650 (17)0.0476 (11)
O220.2050 (3)0.0315 (2)0.13403 (17)0.0516 (11)
O23−0.0887 (4)0.1058 (2)0.0027 (2)0.0589 (12)
H1A−0.037700.14420−0.574600.0510*
H1B0.197100.14380−0.571600.0710*
H2A0.401600.10420−0.017200.0610*
H2B0.318900.12910−0.465900.0710*
H4A−0.049200.11230−0.375200.0630*
H5A−0.164300.12860−0.483100.0640*
H6A0.275600.05030−0.352800.0790*
H6B0.310600.15810−0.320000.0790*
H7A0.075900.06580−0.286100.0740*
H7B0.104900.17400−0.255400.0740*
H9A0.432400.11960−0.223700.0760*
H10A0.540200.11440−0.108100.0750*
H11A0.167300.09640−0.031400.0700*
H12A0.055200.10140−0.142900.0720*
H3B0.418300.36670−0.116600.0670*
H4C0.856400.396900.462900.0510*
H13B0.651700.39940−0.094600.0840*
H14B0.765000.406500.020500.0730*
H16A0.391900.343900.088600.0650*
H17A0.286600.34350−0.028300.0730*
H18B0.749300.423200.156300.0530*
H18C0.712000.316200.133000.0530*
H19B0.542300.451900.222200.0500*
H19C0.506700.344700.199500.0500*
H21'0.860600.380500.247500.0540*
H22'0.978300.382600.361300.0590*
H23'0.623500.410700.463000.0540*
H24A0.499000.410300.351500.0510*
H3A0.149500.613200.404700.0720*
H4B−0.173700.650300.556000.0730*
H5B−0.448900.672600.475400.0850*
H27A−0.002200.614200.295700.0460*
H31A−0.412700.641500.338400.0450*
H8A0.153500.779800.159500.0790*
H9B0.303901.056600.305500.0860*
H10B0.458801.068700.381100.0740*
H34A0.225800.714900.252200.0440*
H38A0.436600.894800.447600.0410*
H13A0.980900.149100.291700.0680*
H14A0.667500.205500.442800.0670*
H15A0.393100.233400.360300.0560*
H41A0.818700.118700.173100.0460*
H45A0.418400.173000.221400.0400*
H18A0.030200.23320−0.005000.0770*
H19A0.149400.478300.052300.0770*
H20A0.156600.579700.203200.0760*
H48A0.053200.209600.129500.0440*
H52A0.247400.442000.287800.0410*
H21A0.009600.667900.143100.0710*
H21B0.022600.619400.064400.0710*
H22A0.239000.017500.172900.0780*
H22B0.274700.055900.117600.0780*
H23A−0.165100.111500.026500.0880*
H23B−0.118300.06250−0.040500.0880*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.042 (2)0.060 (3)0.032 (2)0.009 (2)−0.0031 (18)0.023 (2)
N20.056 (3)0.070 (3)0.028 (2)0.016 (2)−0.007 (2)0.018 (2)
C10.043 (3)0.096 (4)0.049 (3)0.011 (3)0.006 (3)0.039 (3)
C20.032 (3)0.107 (5)0.049 (3)0.012 (3)0.002 (2)0.040 (3)
C30.046 (3)0.058 (3)0.028 (3)0.013 (2)−0.002 (2)0.016 (2)
C40.046 (3)0.084 (4)0.036 (3)0.017 (3)0.008 (2)0.028 (3)
C50.044 (3)0.081 (4)0.042 (3)0.015 (3)−0.002 (3)0.028 (3)
C60.062 (4)0.101 (5)0.042 (3)0.030 (3)−0.004 (3)0.031 (3)
C70.067 (4)0.090 (4)0.035 (3)0.016 (3)−0.005 (3)0.032 (3)
C80.053 (3)0.054 (3)0.037 (3)0.009 (3)−0.008 (2)0.018 (2)
C90.054 (4)0.104 (5)0.043 (3)0.016 (3)0.009 (3)0.037 (3)
C100.051 (3)0.092 (5)0.049 (3)0.011 (3)0.002 (3)0.030 (3)
C110.056 (4)0.082 (4)0.037 (3)0.018 (3)0.002 (3)0.021 (3)
C120.055 (3)0.094 (4)0.041 (3)0.019 (3)0.003 (3)0.034 (3)
N30.052 (3)0.089 (4)0.031 (2)0.014 (2)−0.007 (2)0.027 (2)
N40.054 (3)0.047 (2)0.027 (2)0.000 (2)−0.0111 (19)0.0169 (18)
C130.055 (4)0.123 (6)0.044 (3)0.008 (3)−0.003 (3)0.045 (3)
C140.032 (3)0.108 (5)0.048 (3)0.000 (3)−0.003 (2)0.037 (3)
C150.039 (3)0.052 (3)0.033 (3)0.005 (2)0.000 (2)0.017 (2)
C160.046 (3)0.087 (4)0.036 (3)0.005 (3)−0.001 (2)0.030 (3)
C170.036 (3)0.108 (5)0.038 (3)0.014 (3)−0.005 (2)0.027 (3)
C180.035 (3)0.072 (4)0.032 (3)0.007 (2)−0.006 (2)0.026 (2)
C190.034 (3)0.059 (3)0.035 (3)0.008 (2)−0.007 (2)0.020 (2)
C200.038 (3)0.036 (3)0.028 (2)0.003 (2)−0.004 (2)0.007 (2)
C210.046 (3)0.061 (3)0.033 (3)0.010 (3)−0.001 (2)0.022 (2)
C220.052 (3)0.061 (3)0.034 (3)0.008 (3)−0.007 (2)0.019 (3)
C230.048 (3)0.047 (3)0.040 (3)−0.007 (2)0.003 (2)0.018 (2)
C240.040 (3)0.054 (3)0.034 (3)0.000 (2)−0.001 (2)0.017 (2)
O10.054 (2)0.160 (4)0.038 (2)0.025 (3)0.0006 (18)0.051 (2)
O20.052 (2)0.163 (4)0.044 (2)0.007 (3)0.0105 (19)0.058 (3)
O30.0293 (18)0.084 (3)0.0347 (18)0.0022 (17)−0.0039 (14)0.0272 (18)
O40.049 (2)0.078 (2)0.0246 (17)0.0121 (18)−0.0006 (15)0.0246 (17)
O50.048 (2)0.096 (3)0.037 (2)0.0267 (19)0.0122 (16)0.0341 (19)
C250.047 (3)0.057 (3)0.033 (3)0.005 (2)0.000 (2)0.022 (2)
C260.039 (3)0.042 (3)0.024 (2)0.001 (2)−0.004 (2)0.012 (2)
C270.037 (3)0.053 (3)0.030 (3)0.002 (2)0.005 (2)0.022 (2)
C280.031 (2)0.043 (3)0.031 (3)0.006 (2)−0.005 (2)0.014 (2)
C290.045 (3)0.039 (3)0.023 (2)0.007 (2)−0.004 (2)0.012 (2)
C300.039 (3)0.049 (3)0.030 (3)0.007 (2)0.001 (2)0.018 (2)
C310.034 (3)0.055 (3)0.024 (2)0.008 (2)−0.003 (2)0.014 (2)
O60.059 (2)0.048 (2)0.0269 (18)0.0137 (16)−0.0055 (15)0.0139 (15)
O70.053 (2)0.040 (2)0.0322 (17)0.0013 (16)−0.0031 (15)0.0168 (15)
O80.075 (2)0.049 (2)0.0322 (18)−0.0060 (18)−0.0190 (17)0.0188 (16)
O90.090 (3)0.0366 (19)0.047 (2)−0.0062 (18)−0.0157 (19)0.0209 (17)
O100.069 (2)0.041 (2)0.0363 (18)−0.0134 (17)−0.0082 (16)0.0162 (16)
C320.037 (3)0.042 (3)0.029 (3)0.010 (2)0.002 (2)0.014 (2)
C330.031 (2)0.039 (3)0.030 (2)0.004 (2)−0.002 (2)0.013 (2)
C340.039 (3)0.036 (3)0.032 (3)0.001 (2)−0.007 (2)0.010 (2)
C350.042 (3)0.043 (3)0.029 (3)0.007 (2)−0.007 (2)0.014 (2)
C360.038 (3)0.040 (3)0.035 (3)0.000 (2)−0.001 (2)0.018 (2)
C370.040 (3)0.037 (3)0.031 (3)−0.001 (2)0.000 (2)0.013 (2)
C380.030 (2)0.047 (3)0.026 (2)0.006 (2)−0.0007 (19)0.013 (2)
O110.046 (2)0.090 (3)0.0287 (18)0.0067 (19)−0.0037 (15)0.0224 (18)
O120.055 (2)0.130 (4)0.038 (2)0.005 (2)0.0115 (18)0.032 (2)
O130.0320 (18)0.072 (2)0.0417 (19)0.0050 (16)0.0023 (14)0.0317 (18)
O140.0412 (18)0.064 (2)0.0291 (18)0.0093 (16)−0.0045 (14)0.0169 (16)
O150.0407 (18)0.0471 (19)0.0261 (16)0.0080 (15)0.0012 (14)0.0153 (14)
C390.042 (3)0.055 (3)0.033 (3)0.006 (2)0.001 (2)0.016 (2)
C400.041 (3)0.035 (3)0.029 (2)0.005 (2)0.001 (2)0.009 (2)
C410.037 (3)0.054 (3)0.024 (2)0.006 (2)0.004 (2)0.015 (2)
C420.030 (2)0.040 (3)0.041 (3)−0.001 (2)−0.002 (2)0.018 (2)
C430.040 (3)0.037 (3)0.022 (2)−0.002 (2)−0.006 (2)0.013 (2)
C440.039 (3)0.036 (3)0.021 (2)0.004 (2)−0.0001 (19)0.0104 (19)
C450.033 (2)0.037 (3)0.032 (3)0.004 (2)−0.001 (2)0.014 (2)
O160.054 (2)0.052 (2)0.0302 (18)0.0075 (16)−0.0033 (15)0.0175 (16)
O170.045 (2)0.045 (2)0.0454 (19)0.0023 (16)0.0053 (15)0.0200 (16)
O180.077 (2)0.0431 (19)0.0268 (17)−0.0013 (17)−0.0189 (16)0.0086 (15)
O190.069 (2)0.053 (2)0.0364 (19)−0.0007 (18)−0.0103 (16)0.0239 (17)
O200.075 (2)0.0326 (19)0.043 (2)−0.0025 (17)−0.0101 (17)0.0156 (15)
C460.037 (3)0.041 (3)0.030 (3)0.012 (2)0.007 (2)0.018 (2)
C470.028 (2)0.038 (3)0.024 (2)0.007 (2)−0.0002 (18)0.009 (2)
C480.044 (3)0.034 (3)0.031 (2)−0.001 (2)−0.004 (2)0.012 (2)
C490.041 (3)0.039 (3)0.022 (2)0.002 (2)−0.010 (2)0.008 (2)
C500.044 (3)0.040 (3)0.030 (3)0.002 (2)−0.002 (2)0.016 (2)
C510.045 (3)0.033 (3)0.032 (3)0.003 (2)0.001 (2)0.012 (2)
C520.036 (3)0.039 (3)0.026 (2)0.005 (2)−0.0030 (19)0.011 (2)
O210.052 (2)0.060 (2)0.0297 (17)−0.0049 (17)0.0001 (15)0.0159 (16)
O220.062 (2)0.053 (2)0.0400 (19)−0.0076 (17)−0.0063 (16)0.0198 (17)
O230.055 (2)0.056 (2)0.051 (2)−0.0081 (18)0.0041 (17)0.0012 (18)

Geometric parameters (Å, °)

O1—C251.271 (6)C6—H6B0.9700
O2—C251.220 (6)C7—H7A0.9700
O3—C281.367 (5)C7—H7B0.9700
O4—C291.355 (5)C9—H9A0.9300
O5—C301.375 (5)C10—H10A0.9300
O3—H3A0.8200C11—H11A0.9300
O4—H4B0.8200C12—H12A0.9300
O5—H5B0.8200C13—C141.357 (8)
O6—C321.265 (6)C14—C151.380 (7)
O7—C321.258 (6)C15—C181.507 (6)
O8—C351.369 (5)C15—C161.381 (7)
O9—C361.356 (6)C16—C171.383 (7)
O10—C371.371 (5)C18—C191.518 (6)
O8—H8A0.8200C19—C201.495 (6)
O9—H9B0.8200C20—C211.379 (7)
O10—H10B0.8200C20—C241.384 (6)
O11—C391.272 (6)C21—C221.366 (7)
O12—C391.216 (6)C23—C241.361 (7)
O13—C421.388 (5)C13—H13B0.9300
O14—C431.359 (5)C14—H14B0.9300
O15—C441.374 (5)C16—H16A0.9300
O13—H13A0.8200C17—H17A0.9300
O14—H14A0.8200C18—H18B0.9700
O15—H15A0.8200C18—H18C0.9700
N1—C11.331 (6)C19—H19B0.9700
N1—C51.308 (6)C19—H19C0.9700
N2—C101.328 (7)C21—H21'0.9300
N2—C111.324 (7)C22—H22'0.9300
O16—C461.260 (6)C23—H23'0.9300
O17—C461.269 (6)C24—H24A0.9300
O18—C491.362 (5)C25—C261.497 (6)
O19—C501.367 (5)C26—C311.383 (6)
O20—C511.362 (6)C26—C271.385 (7)
N1—H1A0.8600C27—C281.390 (5)
N2—H2A0.8600C28—C291.389 (6)
O18—H18A0.8200C29—C301.390 (7)
O19—H19A0.8200C30—C311.382 (5)
O20—H20A0.8200C27—H27A0.9300
N3—C131.326 (7)C31—H31A0.9300
N3—C171.324 (7)C32—C331.496 (7)
N4—C231.335 (6)C33—C341.403 (5)
N4—C221.319 (6)C33—C381.382 (6)
N3—H3B0.8600C34—C351.385 (7)
N4—H4C0.8600C35—C361.391 (7)
O21—H21A0.8600C36—C371.381 (6)
O21—H21B0.8600C37—C381.382 (6)
O22—H22B0.8600C34—H34A0.9300
O22—H22A0.8600C38—H38A0.9300
O23—H23A0.8600C39—C401.505 (6)
O23—H23B0.8600C40—C411.389 (7)
C1—C21.347 (7)C40—C451.379 (6)
C2—C31.393 (7)C41—C421.369 (6)
C3—C41.374 (7)C42—C431.391 (6)
C3—C61.517 (8)C43—C441.386 (6)
C4—C51.366 (8)C44—C451.381 (5)
C6—C71.482 (8)C41—H41A0.9300
C7—C81.515 (7)C45—H45A0.9300
C8—C91.370 (7)C46—C471.492 (7)
C8—C121.383 (7)C47—C481.390 (5)
C9—C101.390 (8)C47—C521.392 (7)
C11—C121.348 (8)C48—C491.379 (6)
C1—H1B0.9300C49—C501.400 (7)
C2—H2B0.9300C50—C511.390 (6)
C4—H4A0.9300C51—C521.380 (7)
C5—H5A0.9300C48—H48A0.9300
C6—H6A0.9700C52—H52A0.9300
O1···C13i3.249 (7)C16···H19C2.7800
O1···N3i2.514 (5)C16···H19B3.0100
O2···O212.680 (5)C17···H19A3.0500
O3···C323.217 (6)C18···H21'2.5200
O3···O72.652 (4)C19···H16A2.6800
O3···O42.637 (4)C21···H18C2.7900
O3···N4ii2.804 (5)C21···H18B2.7400
O4···O32.637 (4)C25···H18Biv3.0000
O4···O52.680 (4)C25···H3Bi2.4900
O4···C22ii2.996 (6)C25···H21A3.0600
O4···N4ii3.026 (5)C25···H7Bi3.0700
O4···O16iii2.804 (4)C28···H4Cii2.9900
O5···O6iv2.634 (5)C32···H5Ai3.0800
O5···O42.680 (4)C32···H3A2.4800
O5···O15iii3.027 (5)C32···H31Av2.6800
O6···O5v2.634 (5)C32···H14Aii2.9100
O6···O14ii2.698 (4)C32···H5Bv2.6800
O6···O15ii3.121 (4)C33···H5Ai2.8800
O6···C31v3.409 (5)C34···H20A2.9300
O6···C30v3.349 (6)C34···H4Ai2.9900
O7···C523.400 (5)C35···H4Ai3.0100
O7···O32.652 (4)C36···H22Avi2.9700
O7···O202.608 (4)C38···H5Ai2.7600
O7···C513.370 (6)C39···H2A2.4900
O8···O212.715 (4)C39···H18C3.0100
O8···O92.735 (5)C39···H22B2.9900
O9···O15vi3.153 (4)C45···H22B3.0200
O9···C45vi3.266 (6)C45···H19C3.0500
O9···O22vi2.713 (4)C46···H22'iv2.8800
O9···O102.712 (4)C46···H4Biii2.9800
O9···O82.735 (5)C46···H45A2.7700
O9···C44vi3.254 (6)C46···H15A2.6700
O10···C44vi3.334 (5)C47···H21'iv3.0100
O10···C1vii3.280 (6)C48···H21'iv3.0900
O10···C2vii3.157 (6)C50···H16A2.9800
O10···O15vi2.812 (5)C51···H16A3.0300
O10···O92.712 (4)H1A···H13Aix2.4900
O11···N22.571 (5)H1A···O13ix1.9800
O11···O222.855 (5)H1A···C43ix3.0700
O11···C113.256 (6)H1A···O14ix2.3200
O13···O142.609 (4)H1A···C42ix2.9700
O13···C46v3.410 (6)H1B···H9Bx2.5000
O13···O17v2.569 (4)H1B···O10x2.8400
O14···O152.729 (4)H1B···O15xii2.9100
O14···O132.609 (4)H2A···O111.7400
O15···O5iii3.027 (5)H2A···O122.6000
O15···O142.729 (4)H2A···C392.4900
O15···O162.713 (4)H2B···O10x2.5900
O16···O4iii2.804 (4)H2B···H38Axi2.3800
O16···O152.713 (4)H2B···H6B2.5600
O17···O222.717 (4)H2B···C38xi2.9700
O18···O192.647 (5)H3A···H27A2.3900
O18···O232.623 (5)H3A···H4Cii2.4800
O19···O212.916 (5)H3A···O71.8300
O19···O202.721 (4)H3A···C322.4800
O19···O182.647 (5)H3B···O1i1.6700
O20···C343.265 (6)H3B···C25i2.4900
O20···O192.721 (4)H3B···O2i2.6800
O20···O72.608 (4)H4A···C72.6000
O20···O213.185 (5)H4A···C35i3.0100
O21···O22.680 (5)H4A···H7A2.2800
O21···O192.916 (5)H4A···H7B2.4200
O21···O82.715 (4)H4A···C34i2.9900
O21···O203.185 (5)H4B···O52.2900
O22···O172.717 (4)H4B···C46iii2.9800
O22···O112.855 (5)H4B···O16iii2.0600
O23···C483.225 (5)H4B···H22'ii2.4900
O23···C493.297 (6)H4C···O4ii2.4700
O23···O182.623 (5)H4C···H3Aii2.4800
O23···C113.293 (7)H4C···O3ii1.9700
O1···H3Bi1.6700H4C···C28ii2.9900
O1···H31A2.4100H5A···C38i2.7600
O2···H7Bi2.9100H5A···C32i3.0800
O2···H21B2.7700H5A···H14Aix2.6000
O2···H3Bi2.6800H5A···C33i2.8800
O2···H21A1.9200H5A···O14ix2.4400
O2···H27A2.5600H5B···O15iii2.8000
O3···H4Cii1.9700H5B···C32iv2.6800
O4···H22'ii2.3800H5B···H23'iii2.5700
O4···H4Cii2.4700H5B···O6iv1.8100
O5···H4B2.2900H5B···H31A2.4400
O5···H15Aiii2.8500H6A···C92.9700
O5···H23'iii2.7200H6A···H9A2.5700
O6···H31Av2.8900H6B···H2B2.5600
O6···H38A2.4500H6B···H9A2.3000
O6···H5Bv1.8100H6B···C92.8100
O6···H14Aii1.9400H7A···C42.7900
O7···H3A1.8300H7A···O13xiii2.9000
O7···H52A2.8000H7A···H4A2.2800
O7···H31Av2.7800H7A···H12A2.5100
O7···H27A2.8800H7B···H4A2.4200
O7···H20A2.7500H7B···C42.8300
O7···H34A2.5500H7B···O2i2.9100
O8···H22Avi2.8800H7B···C25i3.0700
O8···H12Ai2.7000H8A···O211.9000
O8···H21A2.8400H8A···H34A2.3200
O9···H10B2.3400H8A···H21A2.0600
O9···H22Avi1.8600H9A···H6B2.3000
O10···H2Bvii2.5900H9A···H6A2.5700
O10···H1Bvii2.8400H9A···C35xi3.0700
O10···H9B2.3400H9A···C36xi2.8500
O10···H38Aviii2.6100H9A···C62.6700
O11···H2A1.7400H9B···O15vi2.4700
O11···H22B1.9900H9B···H22Avi2.3300
O11···H45A2.4600H9B···H10B1.9000
O12···H41A2.6300H9B···O102.3400
O12···H18C2.8300H9B···H1Bvii2.5000
O12···H2A2.6000H9B···C45vi3.0900
O15···H5Biii2.8000H9B···C44vi2.8500
O15···H14A2.3200H10B···C43vi2.8400
O16···H52A2.5400H10B···C44vi2.5300
O16···H22'iv2.9000H10B···O92.3400
O16···H24A2.7100H10B···H9B1.9000
O16···H4Biii2.0600H10B···O15vi2.1200
O16···H15A1.8900H10B···O14vi2.8800
O17···H22A2.7300H11A···O232.5300
O17···H48A2.4600H11A···H18A2.4400
O17···H45A2.8300H12A···H7A2.5100
O19···H20A2.6500H12A···O8i2.7000
O19···H21B2.5400H13A···H41A2.4700
O20···H19A2.6200H13A···C46v2.6500
O20···H34A2.4000H13A···O17v1.7500
O20···H27A2.8300H13B···H19Axi2.4700
O21···H34A2.8200H13B···O21xi2.8500
O21···H8A1.9000H13B···O20xi2.6800
O21···H20A2.5900H14A···O152.3200
O21···H19A2.7700H14B···H18B2.4300
O22···H45A2.8500H14B···H21Bxi2.5800
O23···H11A2.5300H14B···O21xi2.8300
O23···H48A2.5700H15A···H45A2.4200
O23···H18A2.2500H15A···O5iii2.8500
N1···O13ix2.793 (5)H15A···C462.6700
N1···O14ix2.914 (5)H15A···O161.8900
N2···O112.571 (5)H16A···C513.0300
N2···C393.326 (6)H16A···C502.9800
N3···C25i3.335 (6)H16A···C192.6800
N3···O1i2.514 (5)H16A···H19C2.2400
N4···C29v3.344 (7)H17A···H19A2.5600
N4···C433.442 (6)H18A···O232.2500
N4···O3ii2.804 (5)H18A···H11A2.4400
N4···O4ii3.026 (5)H18A···C122.9100
C1···O13ix3.414 (6)H18A···C112.7900
C1···O10x3.280 (6)H18B···H14B2.4300
C1···C30i3.490 (8)H18B···H21'2.2200
C1···C29i3.424 (8)H18B···C212.7400
C2···C30i3.471 (8)H18B···C25v3.0000
C2···O10x3.157 (6)H18C···H21'2.3300
C2···C31i3.538 (7)H18C···C393.0100
C5···O14ix2.984 (6)H18C···C212.7900
C5···C38i3.522 (6)H18C···O122.8300
C5···C33i3.502 (6)H19A···H21B2.4800
C11···O113.256 (6)H19A···O212.7700
C11···O233.293 (7)H19A···O202.6200
C13···O21xi3.395 (6)H19A···H17A2.5600
C13···O1i3.249 (7)H19A···C173.0500
C14···O21xi3.375 (6)H19B···C163.0100
C16···C503.560 (7)H19C···C453.0500
C20···C31v3.468 (7)H19C···C162.7800
C20···C453.531 (7)H19C···H16A2.2400
C21···C27v3.488 (7)H20A···O212.5900
C21···C28v3.564 (7)H20A···H34A2.0100
C22···C28v3.331 (7)H20A···O72.7500
C22···C423.567 (7)H20A···H27A2.2800
C22···C29v3.494 (7)H20A···C342.9300
C22···O4ii2.996 (6)H20A···H21A2.4400
C23···C30v3.465 (7)H20A···O192.6500
C23···C29v3.542 (7)H21'···C48v3.0900
C23···C433.454 (7)H21'···H18C2.3300
C23···C443.433 (7)H21'···C182.5200
C24···C443.289 (7)H21'···C47v3.0100
C24···C453.564 (7)H21'···H18B2.2200
C24···C31v3.584 (7)H21A···O82.8400
C24···C30v3.419 (7)H21A···O21.9200
C25···N3i3.335 (6)H21A···C253.0600
C27···C21iv3.488 (7)H21A···H20A2.4400
C28···C21iv3.564 (7)H21A···H8A2.0600
C28···C22iv3.331 (7)H21B···O22.7700
C29···C22iv3.494 (7)H21B···H19A2.4800
C29···C23iv3.542 (7)H21B···O192.5400
C29···C1i3.424 (8)H22'···H4Bii2.4900
C29···N4iv3.344 (7)H22'···O4ii2.3800
C30···C24iv3.419 (7)H22'···C46v2.8800
C30···C23iv3.465 (7)H22'···O16v2.9000
C30···C2i3.471 (8)H22A···O172.7300
C30···C1i3.490 (8)H22B···C392.9900
C30···O6iv3.349 (6)H22B···H45A2.4000
C31···C32iv3.467 (7)H22B···O111.9900
C31···C2i3.538 (7)H22B···C453.0200
C31···C24iv3.584 (7)H23'···O5iii2.7200
C31···O6iv3.409 (5)H23'···H5Biii2.5700
C31···C20iv3.468 (7)H24A···O162.7100
C32···C31v3.467 (7)H27A···O202.8300
C32···O33.217 (6)H27A···H3A2.3900
C33···C5i3.502 (6)H27A···O72.8800
C34···O203.265 (6)H27A···O22.5600
C38···C5i3.522 (6)H27A···H20A2.2800
C39···N23.326 (6)H31A···O12.4100
C42···C223.567 (7)H31A···H5B2.4400
C42···O17v3.393 (5)H31A···C32iv2.6800
C43···C233.454 (7)H31A···O6iv2.8900
C43···N43.442 (6)H31A···O7iv2.7800
C44···C233.433 (7)H34A···O202.4000
C44···C243.289 (7)H34A···O212.8200
C45···C463.552 (7)H34A···H20A2.0100
C45···C243.564 (7)H34A···H8A2.3200
C45···C203.531 (7)H34A···O72.5500
C46···C453.552 (7)H38A···O10viii2.6100
C48···O233.225 (5)H38A···O62.4500
C49···O233.297 (6)H41A···O122.6300
C50···C163.560 (7)H41A···H13A2.4700
C51···O73.370 (6)H45A···O172.8300
C52···O73.400 (5)H45A···O222.8500
C4···H7B2.8300H45A···C462.7700
C4···H7A2.7900H45A···H15A2.4200
C6···H9A2.6700H45A···H22B2.4000
C7···H4A2.6000H45A···O112.4600
C9···H6B2.8100H48A···O172.4600
C9···H6A2.9700H48A···O232.5700
C11···H18A2.7900H52A···O72.8000
C12···H18A2.9100H52A···O162.5400
C13···H19Axi3.0300
C28—O3—H3A110C18—C19—H19C109
C29—O4—H4B109C20—C19—H19B109
C30—O5—H5B109H19B—C19—H19C108
C35—O8—H8A109C20—C19—H19C109
C36—O9—H9B110C18—C19—H19B109
C37—O10—H10B109C22—C21—H21'120
C42—O13—H13A110C20—C21—H21'120
C43—O14—H14A110N4—C22—H22'120
C44—O15—H15A109C21—C22—H22'120
C1—N1—C5121.8 (4)N4—C23—H23'120
C10—N2—C11120.7 (4)C24—C23—H23'120
C1—N1—H1A119C23—C24—H24A120
C5—N1—H1A119C20—C24—H24A120
C11—N2—H2A120O1—C25—C26115.4 (4)
C10—N2—H2A120O1—C25—O2122.4 (5)
C49—O18—H18A109O2—C25—C26122.2 (4)
C50—O19—H19A109C25—C26—C27119.5 (4)
C51—O20—H20A110C25—C26—C31119.5 (4)
C13—N3—C17118.5 (4)C27—C26—C31121.0 (4)
C22—N4—C23121.1 (4)C26—C27—C28119.2 (4)
C17—N3—H3B121C27—C28—C29120.4 (4)
C13—N3—H3B121O3—C28—C29115.6 (3)
C22—N4—H4C119O3—C28—C27124.0 (4)
C23—N4—H4C119C28—C29—C30119.4 (3)
H21A—O21—H21B109O4—C29—C30121.6 (4)
H22A—O22—H22B107O4—C29—C28119.0 (4)
H23A—O23—H23B100C29—C30—C31120.7 (4)
N1—C1—C2120.1 (5)O5—C30—C31124.5 (4)
C1—C2—C3121.0 (5)O5—C30—C29114.9 (3)
C2—C3—C6119.6 (4)C26—C31—C30119.3 (4)
C2—C3—C4116.1 (5)C26—C27—H27A120
C4—C3—C6124.3 (5)C28—C27—H27A120
C3—C4—C5121.2 (5)C26—C31—H31A120
N1—C5—C4120.0 (4)C30—C31—H31A120
C3—C6—C7115.2 (5)O6—C32—C33117.3 (4)
C6—C7—C8117.2 (5)O7—C32—C33119.7 (4)
C7—C8—C9124.8 (5)O6—C32—O7123.0 (4)
C9—C8—C12117.1 (5)C32—C33—C38119.6 (4)
C7—C8—C12118.1 (5)C34—C33—C38119.8 (4)
C8—C9—C10120.7 (5)C32—C33—C34120.5 (4)
N2—C10—C9119.5 (5)C33—C34—C35119.4 (4)
N2—C11—C12121.7 (5)O8—C35—C36116.6 (4)
C8—C12—C11120.4 (5)C34—C35—C36120.5 (4)
C2—C1—H1B120O8—C35—C34123.0 (4)
N1—C1—H1B120O9—C36—C37117.9 (4)
C3—C2—H2B120C35—C36—C37119.5 (4)
C1—C2—H2B120O9—C36—C35122.6 (4)
C5—C4—H4A119C36—C37—C38120.6 (4)
C3—C4—H4A119O10—C37—C38118.8 (3)
C4—C5—H5A120O10—C37—C36120.5 (4)
N1—C5—H5A120C33—C38—C37120.1 (3)
C3—C6—H6A109C35—C34—H34A120
H6A—C6—H6B107C33—C34—H34A120
C7—C6—H6B108C33—C38—H38A120
C3—C6—H6B109C37—C38—H38A120
C7—C6—H6A108O11—C39—O12122.0 (5)
C6—C7—H7A108O11—C39—C40116.0 (4)
C6—C7—H7B108O12—C39—C40121.9 (4)
C8—C7—H7B108C41—C40—C45119.5 (3)
H7A—C7—H7B107C39—C40—C45119.5 (4)
C8—C7—H7A108C39—C40—C41121.0 (4)
C10—C9—H9A120C40—C41—C42120.3 (4)
C8—C9—H9A120C41—C42—C43120.2 (4)
C9—C10—H10A120O13—C42—C41124.9 (4)
N2—C10—H10A120O13—C42—C43114.9 (4)
N2—C11—H11A119C42—C43—C44119.5 (4)
C12—C11—H11A119O14—C43—C44122.7 (4)
C8—C12—H12A120O14—C43—C42117.7 (4)
C11—C12—H12A120O15—C44—C45124.0 (4)
N3—C13—C14122.3 (5)C43—C44—C45119.8 (4)
C13—C14—C15120.5 (5)O15—C44—C43116.2 (3)
C16—C15—C18123.1 (5)C40—C45—C44120.5 (4)
C14—C15—C16117.2 (5)C42—C41—H41A120
C14—C15—C18119.7 (4)C40—C41—H41A120
C15—C16—C17118.9 (5)C40—C45—H45A120
N3—C17—C16122.6 (5)C44—C45—H45A120
C15—C18—C19116.3 (4)O16—C46—O17123.0 (4)
C18—C19—C20114.9 (4)O16—C46—C47119.4 (4)
C19—C20—C21122.4 (4)O17—C46—C47117.6 (4)
C21—C20—C24117.1 (4)C46—C47—C52120.8 (3)
C19—C20—C24120.5 (4)C48—C47—C52119.3 (4)
C20—C21—C22120.6 (4)C46—C47—C48119.9 (4)
N4—C22—C21120.4 (4)C47—C48—C49121.3 (4)
N4—C23—C24120.4 (5)O18—C49—C48124.3 (4)
C20—C24—C23120.4 (4)O18—C49—C50116.6 (4)
C14—C13—H13B119C48—C49—C50119.1 (3)
N3—C13—H13B119C49—C50—C51119.7 (4)
C13—C14—H14B120O19—C50—C49117.8 (3)
C15—C14—H14B120O19—C50—C51122.5 (4)
C17—C16—H16A120O20—C51—C50115.9 (4)
C15—C16—H16A121O20—C51—C52123.5 (4)
C16—C17—H17A119C50—C51—C52120.6 (4)
N3—C17—H17A119C47—C52—C51120.0 (4)
C19—C18—H18C108C47—C48—H48A119
C15—C18—H18B108C49—C48—H48A119
C19—C18—H18B108C47—C52—H52A120
C15—C18—H18C108C51—C52—H52A120
H18B—C18—H18C107
C5—N1—C1—C2−0.6 (9)C29—C30—C31—C26−0.9 (7)
C1—N1—C5—C40.3 (9)O6—C32—C33—C34−178.5 (4)
C10—N2—C11—C12−0.6 (9)O6—C32—C33—C38−0.2 (6)
C11—N2—C10—C90.6 (9)O7—C32—C33—C341.6 (6)
C13—N3—C17—C16−2.1 (9)O7—C32—C33—C38179.9 (4)
C17—N3—C13—C140.9 (10)C32—C33—C34—C35179.3 (4)
C23—N4—C22—C21−0.3 (8)C38—C33—C34—C351.1 (6)
C22—N4—C23—C240.0 (8)C32—C33—C38—C37−179.8 (4)
N1—C1—C2—C30.8 (9)C34—C33—C38—C37−1.5 (6)
C1—C2—C3—C6−179.1 (6)C33—C34—C35—O8179.2 (4)
C1—C2—C3—C4−0.6 (9)C33—C34—C35—C36−1.5 (6)
C4—C3—C6—C7−9.0 (9)O8—C35—C36—O90.6 (7)
C6—C3—C4—C5178.7 (6)O8—C35—C36—C37−178.3 (4)
C2—C3—C6—C7169.4 (6)C34—C35—C36—O9−178.8 (4)
C2—C3—C4—C50.3 (9)C34—C35—C36—C372.4 (7)
C3—C4—C5—N1−0.2 (9)O9—C36—C37—O10−0.6 (7)
C3—C6—C7—C8−177.6 (5)O9—C36—C37—C38178.3 (4)
C6—C7—C8—C12−171.0 (6)C35—C36—C37—O10178.3 (4)
C6—C7—C8—C99.3 (9)C35—C36—C37—C38−2.8 (7)
C7—C8—C9—C10179.2 (6)O10—C37—C38—C33−178.7 (4)
C7—C8—C12—C11−179.2 (6)C36—C37—C38—C332.4 (6)
C12—C8—C9—C10−0.5 (9)O11—C39—C40—C41164.2 (5)
C9—C8—C12—C110.5 (9)O11—C39—C40—C45−15.1 (7)
C8—C9—C10—N20.0 (9)O12—C39—C40—C41−16.3 (8)
N2—C11—C12—C80.0 (9)O12—C39—C40—C45164.5 (5)
N3—C13—C14—C151.1 (10)C39—C40—C41—C42−176.8 (5)
C13—C14—C15—C18178.0 (6)C45—C40—C41—C422.5 (7)
C13—C14—C15—C16−1.8 (9)C39—C40—C45—C44178.2 (4)
C16—C15—C18—C19−23.1 (8)C41—C40—C45—C44−1.1 (7)
C18—C15—C16—C17−179.2 (5)C40—C41—C42—O13177.6 (4)
C14—C15—C18—C19157.1 (5)C40—C41—C42—C43−1.7 (7)
C14—C15—C16—C170.6 (8)O13—C42—C43—O141.9 (6)
C15—C16—C17—N31.4 (9)O13—C42—C43—C44−179.8 (4)
C15—C18—C19—C20−179.2 (5)C41—C42—C43—O14−178.8 (4)
C18—C19—C20—C24−175.8 (5)C41—C42—C43—C44−0.5 (7)
C18—C19—C20—C213.4 (8)O14—C43—C44—O15−1.0 (7)
C24—C20—C21—C220.0 (7)O14—C43—C44—C45−179.9 (4)
C19—C20—C21—C22−179.2 (5)C42—C43—C44—O15−179.2 (4)
C19—C20—C24—C23179.0 (5)C42—C43—C44—C451.9 (7)
C21—C20—C24—C23−0.3 (7)O15—C44—C45—C40−180.0 (4)
C20—C21—C22—N40.3 (8)C43—C44—C45—C40−1.1 (7)
N4—C23—C24—C200.3 (8)O16—C46—C47—C48175.2 (4)
O1—C25—C26—C27176.5 (5)O16—C46—C47—C52−5.2 (6)
O1—C25—C26—C31−1.7 (7)O17—C46—C47—C48−3.4 (6)
O2—C25—C26—C27−2.2 (7)O17—C46—C47—C52176.2 (4)
O2—C25—C26—C31179.5 (5)C46—C47—C48—C49179.7 (4)
C25—C26—C27—C28−178.5 (4)C52—C47—C48—C490.0 (6)
C31—C26—C27—C28−0.3 (7)C46—C47—C52—C51−179.8 (4)
C25—C26—C31—C30179.9 (4)C48—C47—C52—C51−0.2 (6)
C27—C26—C31—C301.6 (7)C47—C48—C49—O18−179.7 (4)
C26—C27—C28—O3177.6 (4)C47—C48—C49—C50−0.7 (6)
C26—C27—C28—C29−1.8 (7)O18—C49—C50—O190.3 (6)
O3—C28—C29—O42.8 (6)O18—C49—C50—C51−179.4 (4)
O3—C28—C29—C30−176.9 (4)C48—C49—C50—O19−178.8 (4)
C27—C28—C29—O4−177.7 (4)C48—C49—C50—C511.6 (6)
C27—C28—C29—C302.6 (7)O19—C50—C51—O20−3.9 (7)
O4—C29—C30—O5−0.5 (7)O19—C50—C51—C52178.6 (4)
O4—C29—C30—C31179.0 (4)C49—C50—C51—O20175.7 (4)
C28—C29—C30—O5179.3 (4)C49—C50—C51—C52−1.7 (7)
C28—C29—C30—C31−1.2 (7)O20—C51—C52—C47−176.2 (4)
O5—C30—C31—C26178.6 (5)C50—C51—C52—C471.1 (7)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z; (v) x+1, y, z; (vi) x, y+1, z; (vii) x, y+1, z+1; (viii) −x+1, −y+2, −z+1; (ix) x−1, y, z−1; (x) x, y−1, z−1; (xi) −x+1, −y+1, −z; (xii) x, y, z−1; (xiii) −x+1, −y, −z.

Hydrogen-bond geometry (Å, °)

Cg6 and Cg8 are the centroids of the C33–C38 and C47–C52 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1A···O13ix0.861.982.793 (5)158
N1—H1A···O14ix0.862.322.914 (5)127
N2—H2A···O110.861.742.571 (5)163
N2—H2A···O120.862.603.297 (5)139
N3—H3B···O1i0.861.672.514 (5)166
N4—H4C···O3ii0.861.972.804 (5)165
N4—H4C···O4ii0.862.473.026 (5)123
O3—H3A···O70.821.832.652 (4)175
O4—H4B···O16iii0.822.062.804 (4)151
O5—H5B···O6iv0.821.812.634 (5)180
O8—H8A···O210.821.902.715 (4)175
O9—H9B···O15vi0.822.473.153 (4)141
O10—H10B···O15vi0.822.122.812 (5)142
O13—H13A···O17v0.821.752.569 (4)172
O14—H14A···O150.822.322.729 (4)111
O15—H15A···O160.821.892.713 (4)179
O18—H18A···O230.822.252.623 (5)108
O20—H20A···O210.822.593.185 (5)131
O21—H21A···O20.861.922.680 (5)148
O21—H21B···O19i0.862.323.163 (4)165
O22—H22A···O9xiv0.861.862.713 (4)170
O22—H22B···O110.861.992.855 (5)179
O23—H23A···O12iv0.861.802.637 (5)166
O23—H23B···O22xv0.861.922.781 (5)174
C11—H11A···O230.932.533.293 (7)139
C34—H34A···O200.932.403.265 (6)154
C4—H4A···Cg6i0.932.813.571 (5)140
C16—H16A···Cg80.932.913.737 (5)149

Symmetry codes: (ix) x−1, y, z−1; (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, y, z; (vi) x, y+1, z; (v) x+1, y, z; (xiv) x, y−1, z; (xv) −x, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2790).

References

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  • Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.
  • Okabe, N., Kyoyama, H. & Suzuki, M. (2001). Acta Cryst. E57, o764–o766.
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