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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1572.
Published online 2010 June 5. doi:  10.1107/S1600536810016764
PMCID: PMC3006681

(5S*,6R*,7R*)-6-Formyl-5-phenyl-7-propyl­perhydro­pyrazolo[1,2-a]pyrazol-1-one

Abstract

The title compound, C16H20N2O2, was obtained by catalytic asymmetric cyclo­addition of trans-3-propyl­acrolein with 1-benzyl­idenepyrazolid-3-one betaine. There are two symmetry-independent mol­ecules in the asymmetric unit. In both mol­ecules, the two five-membered heterocyclic rings adopt envelope conformations.

Related literature

For the biological activity of bicylic pyrazolidinone derivatives, see: Indelicato & Pasini (1988 [triangle]); Jungheim & Sigmund (1987 [triangle]). For synthetic methods of five-membered bicyclic heterocycles, see: Chen et al. (2006 [triangle], 2007 [triangle]).

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Object name is e-66-o1572-scheme1.jpg

Experimental

Crystal data

  • C16H20N2O2
  • M r = 272.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1572-efi1.jpg
  • a = 8.557 (2) Å
  • b = 13.839 (3) Å
  • c = 13.905 (3) Å
  • α = 60.50 (3)°
  • β = 81.12 (3)°
  • γ = 81.22 (3)°
  • V = 1410.4 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 113 K
  • 0.18 × 0.16 × 0.14 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.985, T max = 0.988
  • 12841 measured reflections
  • 6619 independent reflections
  • 3540 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.112
  • S = 0.89
  • 6619 reflections
  • 365 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016764/lx2144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016764/lx2144Isup2.hkl

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

Acknowledgments

The authors thank the Beijing Institute of Technology for financial support.

supplementary crystallographic information

Comment

Bicylic pyrazolidinone derivatives are biologically active compounds, such as LY186826 exhibits high anti-bacterial activity (Jungheim et al. 1987; Indelicato et al. 1988). Recently, small organic molecules-catalysed asymmetric [3 + 2] dipolar cycloaddition of azomethine imines with alpha, beta-unsaturated aldehydes provides one of the most powerful strategies for the stereoselective synthesis of this five-membered bicyclic heterocycle (Chen et al.., 2006, 2007).). We observed that trifluoroacetic acid salt of 2-(pyrrolidinylmethyl)pyrrolidine catalyzes the synthesis of a series of bipyrazolidinone with excellent stereoselectivity.

We report the crystal structure of title compound, (2R,3R,4S)-2-propyl-3-formyl-4-phenyl-2,3,4,5- tetrahydropyrazolo [1,2-a] pyrazolidin-8-one (Fig. 1). There are two symmetry-independent molecules (A & B) in the asymmetric unit. In the title compound, two 5-membered heterocyclic rings adopt envelope conformation, and the configuration of the chiral centers, C7 (C23)S, C8 (C24)R and C9 (C25)R was assigned.

Experimental

The trans-3-propyl-acrolein (39.3 mg, 0.4 mmol) was added to a mixture of 1-phenylidenepyrazolid-3-one (32.4 mg, 0.2 mmol), catalyst trifluoroacetic acid salt of 2-(pyrrolidinylmethyl)pyrrolidine (5.4 mg, 0.02 mmol) and water (6 muL) in THF (2.0 ml) at 10 °. the mixture was stirred at this temperature for 12 h. EtOAc (10 ml) was added, and the solution was washed with water, The organic phase was dried (Na2SO4), and concentrated under reduced pressure. The residue was isolated through short column chromatography on silica gel,which was eluded with EtOAc–petroleum to give the target compound(51.4 mg, 94%). 30 mg of the obtained product was dissolved in ethyl acetate (4 ml) and petroleum (1 ml) and the solution was kept at room temperature for 3 days to give colorless single crystals.

Refinement

C—H were included in the riding model approximation with C—H distances 0.95–1.00 Å, and with Uiso = 1.2Ueq or 1.5Ueq(methyl).

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small cycles of arbitrary radius.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis

Crystal data

C16H20N2O2Z = 4
Mr = 272.34F(000) = 584
Triclinic, P1Dx = 1.283 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.557 (2) ÅCell parameters from 4363 reflections
b = 13.839 (3) Åθ = 1.7–27.9°
c = 13.905 (3) ŵ = 0.09 mm1
α = 60.50 (3)°T = 113 K
β = 81.12 (3)°Block, colourless
γ = 81.22 (3)°0.18 × 0.16 × 0.14 mm
V = 1410.4 (7) Å3

Data collection

Rigaku Saturn CCD area-detector diffractometer6619 independent reflections
Radiation source: rotating anode3540 reflections with I > 2σ(I)
confocalRint = 0.058
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.7°
ω and [var phi] scansh = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −18→17
Tmin = 0.985, Tmax = 0.988l = −18→18
12841 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)] = 0.043H-atom parameters constrained
wR(F2) = 0.112w = 1/[σ2(Fo2) + (0.039P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.001
6619 reflectionsΔρmax = 0.30 e Å3
365 parametersΔρmin = −0.23 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: 0.032 (2)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. 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
O1−0.36894 (19)0.16690 (15)0.55617 (16)0.0407 (5)
O20.24237 (17)0.28648 (12)0.22370 (13)0.0234 (4)
N10.1158 (2)0.12298 (14)0.50583 (15)0.0182 (4)
N20.1077 (2)0.21896 (14)0.39611 (15)0.0183 (4)
C1−0.0489 (3)0.11013 (18)0.77713 (19)0.0225 (5)
H1−0.03660.18410.76010.027*
C2−0.0993 (3)0.03419 (19)0.8840 (2)0.0262 (5)
H2−0.12210.05620.93980.031*
C3−0.1168 (3)−0.07422 (19)0.9102 (2)0.0254 (5)
H3−0.1509−0.12670.98390.031*
C4−0.0848 (3)−0.10551 (18)0.82884 (19)0.0231 (5)
H4−0.0969−0.17970.84650.028*
C5−0.0344 (2)−0.02851 (18)0.72022 (19)0.0205 (5)
H5−0.0127−0.05060.66440.025*
C6−0.0159 (2)0.07985 (17)0.69382 (18)0.0181 (5)
C70.0306 (2)0.16824 (17)0.57711 (18)0.0181 (4)
H70.09780.21980.57990.022*
C8−0.1124 (2)0.23707 (18)0.50937 (18)0.0182 (5)
H8−0.16310.29300.53300.022*
C9−0.0349 (2)0.29584 (17)0.38872 (18)0.0177 (5)
H9−0.10570.29800.33670.021*
C100.0068 (2)0.41278 (17)0.35206 (19)0.0203 (5)
H10A0.05580.41210.41240.024*
H10B0.08590.43570.28650.024*
C11−0.1376 (3)0.49711 (18)0.3231 (2)0.0233 (5)
H11A−0.22200.46890.38510.028*
H11B−0.17820.50470.25660.028*
C12−0.1025 (3)0.61126 (19)0.3005 (2)0.0361 (6)
H12A−0.06380.60460.36650.054*
H12B−0.19970.66200.28290.054*
H12C−0.02130.64070.23770.054*
C130.2890 (2)0.09474 (19)0.51073 (19)0.0229 (5)
H13A0.31430.01490.56290.028*
H13B0.33640.14060.53330.028*
C140.3474 (2)0.12225 (18)0.39071 (19)0.0220 (5)
H14A0.45760.14390.37140.026*
H14B0.34240.05820.37840.026*
C150.2308 (2)0.22009 (18)0.32376 (18)0.0193 (5)
C16−0.2324 (3)0.16164 (19)0.52082 (19)0.0247 (5)
H16−0.19770.10640.49860.030*
O30.75718 (19)0.66942 (15)0.05764 (16)0.0376 (5)
O40.25782 (17)0.78835 (12)−0.27499 (13)0.0240 (4)
N30.3203 (2)0.62734 (14)0.00751 (15)0.0185 (4)
N40.3364 (2)0.72338 (14)−0.10197 (15)0.0193 (4)
C170.3464 (3)0.60910 (19)0.28130 (19)0.0241 (5)
H170.30530.68260.26580.029*
C180.3752 (3)0.5307 (2)0.3887 (2)0.0278 (6)
H180.35450.55040.44620.033*
C190.4346 (3)0.42289 (19)0.4124 (2)0.0258 (5)
H190.45350.36840.48630.031*
C200.4659 (3)0.39539 (19)0.3285 (2)0.0236 (5)
H200.50750.32180.34460.028*
C210.4371 (2)0.47424 (18)0.22027 (19)0.0212 (5)
H210.45890.45430.16290.025*
C220.3764 (2)0.58269 (18)0.19570 (19)0.0182 (5)
C230.3467 (2)0.67224 (18)0.07920 (18)0.0180 (5)
H230.25260.72370.08200.022*
C240.4902 (2)0.74133 (18)0.01171 (18)0.0195 (5)
H240.50230.79680.03580.023*
C250.4435 (2)0.80044 (17)−0.10890 (18)0.0183 (5)
H250.53960.8023−0.16070.022*
C260.3621 (2)0.91800 (17)−0.14786 (19)0.0200 (5)
H26A0.31510.9424−0.21790.024*
H26B0.27440.9163−0.09170.024*
C270.4735 (3)1.00255 (19)−0.1668 (2)0.0273 (5)
H27A0.51920.9790−0.09650.033*
H27B0.56211.0036−0.22220.033*
C280.3917 (3)1.11944 (18)−0.2072 (2)0.0310 (6)
H28A0.34691.1436−0.27710.047*
H28B0.46901.1706−0.21900.047*
H28C0.30631.1196−0.15150.047*
C290.6404 (3)0.66558 (19)0.02194 (19)0.0258 (5)
H290.64290.6113−0.00130.031*
C300.1594 (2)0.5981 (2)0.0128 (2)0.0238 (5)
H30A0.07720.64390.03490.029*
H30B0.14800.51820.06510.029*
C310.1497 (3)0.62509 (18)−0.10728 (19)0.0226 (5)
H31A0.19360.5608−0.11900.027*
H31B0.03880.6462−0.12710.027*
C320.2509 (3)0.72308 (18)−0.17447 (19)0.0202 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0188 (9)0.0407 (12)0.0407 (12)−0.0039 (8)0.0014 (8)−0.0037 (9)
O20.0257 (9)0.0238 (9)0.0185 (9)−0.0027 (7)0.0015 (7)−0.0093 (7)
N10.0192 (9)0.0164 (10)0.0148 (10)0.0001 (8)−0.0005 (8)−0.0051 (7)
N20.0186 (9)0.0161 (10)0.0147 (10)−0.0001 (7)0.0003 (8)−0.0041 (7)
C10.0258 (12)0.0205 (12)0.0215 (13)0.0000 (9)−0.0036 (10)−0.0106 (10)
C20.0286 (13)0.0319 (14)0.0196 (13)−0.0005 (10)−0.0018 (10)−0.0142 (11)
C30.0237 (12)0.0272 (13)0.0185 (12)−0.0025 (10)−0.0006 (10)−0.0061 (10)
C40.0221 (12)0.0188 (12)0.0237 (13)−0.0019 (9)−0.0036 (10)−0.0062 (10)
C50.0217 (12)0.0197 (12)0.0206 (12)0.0001 (9)−0.0033 (10)−0.0101 (10)
C60.0144 (11)0.0195 (12)0.0192 (12)0.0015 (9)−0.0047 (9)−0.0082 (9)
C70.0205 (11)0.0169 (11)0.0173 (12)−0.0025 (9)−0.0018 (9)−0.0082 (9)
C80.0183 (11)0.0172 (11)0.0159 (11)0.0004 (9)−0.0001 (9)−0.0064 (9)
C90.0157 (11)0.0174 (11)0.0186 (12)0.0008 (9)−0.0020 (9)−0.0081 (9)
C100.0195 (11)0.0198 (12)0.0210 (12)−0.0031 (9)0.0001 (9)−0.0094 (9)
C110.0246 (12)0.0185 (12)0.0225 (13)−0.0004 (10)−0.0030 (10)−0.0068 (10)
C120.0433 (16)0.0225 (14)0.0423 (17)0.0022 (11)−0.0065 (13)−0.0162 (12)
C130.0188 (11)0.0244 (13)0.0231 (13)0.0015 (9)−0.0035 (10)−0.0100 (10)
C140.0186 (11)0.0205 (12)0.0255 (13)−0.0004 (9)0.0016 (10)−0.0115 (10)
C150.0201 (11)0.0194 (12)0.0199 (13)−0.0037 (9)0.0008 (9)−0.0108 (10)
C160.0197 (12)0.0240 (13)0.0207 (13)−0.0032 (10)−0.0055 (10)−0.0022 (10)
O30.0236 (9)0.0385 (11)0.0368 (11)−0.0081 (8)−0.0111 (8)−0.0039 (8)
O40.0277 (9)0.0255 (9)0.0189 (9)−0.0003 (7)−0.0049 (7)−0.0105 (7)
N30.0213 (10)0.0181 (10)0.0148 (10)−0.0049 (8)−0.0023 (8)−0.0059 (7)
N40.0208 (10)0.0199 (10)0.0149 (10)−0.0029 (8)−0.0030 (8)−0.0059 (8)
C170.0243 (12)0.0252 (13)0.0227 (13)0.0016 (10)−0.0029 (10)−0.0122 (10)
C180.0302 (13)0.0331 (14)0.0196 (13)0.0004 (11)−0.0022 (11)−0.0131 (11)
C190.0255 (12)0.0267 (13)0.0204 (13)−0.0050 (10)−0.0033 (10)−0.0065 (10)
C200.0204 (12)0.0211 (12)0.0256 (13)−0.0017 (9)−0.0053 (10)−0.0075 (10)
C210.0218 (12)0.0211 (12)0.0210 (12)−0.0032 (9)−0.0016 (10)−0.0101 (10)
C220.0156 (10)0.0204 (12)0.0195 (12)−0.0039 (9)−0.0017 (9)−0.0097 (9)
C230.0182 (11)0.0200 (12)0.0171 (12)−0.0016 (9)−0.0017 (9)−0.0099 (9)
C240.0212 (11)0.0180 (12)0.0167 (12)−0.0044 (9)−0.0016 (9)−0.0055 (9)
C250.0173 (11)0.0221 (12)0.0168 (12)−0.0039 (9)−0.0010 (9)−0.0099 (9)
C260.0188 (11)0.0188 (12)0.0202 (12)0.0010 (9)−0.0030 (9)−0.0082 (9)
C270.0260 (13)0.0242 (13)0.0295 (14)−0.0024 (10)−0.0054 (11)−0.0104 (11)
C280.0386 (15)0.0221 (13)0.0335 (15)−0.0028 (11)−0.0036 (12)−0.0140 (11)
C290.0190 (12)0.0253 (13)0.0216 (13)−0.0050 (10)−0.0024 (10)−0.0014 (10)
C300.0209 (12)0.0280 (13)0.0229 (13)−0.0061 (10)−0.0039 (10)−0.0109 (10)
C310.0236 (12)0.0212 (12)0.0245 (13)−0.0034 (10)−0.0078 (10)−0.0101 (10)
C320.0201 (11)0.0204 (12)0.0214 (13)0.0027 (9)−0.0051 (10)−0.0115 (10)

Geometric parameters (Å, °)

O1—C161.201 (3)O3—C291.201 (3)
O2—C151.231 (3)O4—C321.233 (3)
N1—N21.451 (2)N3—N41.450 (2)
N1—C71.468 (3)N3—C231.468 (3)
N1—C131.478 (3)N3—C301.475 (3)
N2—C151.336 (3)N4—C321.336 (3)
N2—C91.472 (3)N4—C251.468 (3)
C1—C21.379 (3)C17—C181.380 (3)
C1—C61.392 (3)C17—C221.386 (3)
C1—H10.9500C17—H170.9500
C2—C31.386 (3)C18—C191.389 (3)
C2—H20.9500C18—H180.9500
C3—C41.375 (3)C19—C201.373 (3)
C3—H30.9500C19—H190.9500
C4—C51.399 (3)C20—C211.390 (3)
C4—H40.9500C20—H200.9500
C5—C61.386 (3)C21—C221.397 (3)
C5—H50.9500C21—H210.9500
C6—C71.511 (3)C22—C231.509 (3)
C7—C81.552 (3)C23—C241.556 (3)
C7—H71.0000C23—H231.0000
C8—C161.511 (3)C24—C291.507 (3)
C8—C91.547 (3)C24—C251.548 (3)
C8—H81.0000C24—H241.0000
C9—C101.521 (3)C25—C261.526 (3)
C9—H91.0000C25—H251.0000
C10—C111.517 (3)C26—C271.519 (3)
C10—H10A0.9900C26—H26A0.9900
C10—H10B0.9900C26—H26B0.9900
C11—C121.521 (3)C27—C281.518 (3)
C11—H11A0.9900C27—H27A0.9900
C11—H11B0.9900C27—H27B0.9900
C12—H12A0.9800C28—H28A0.9800
C12—H12B0.9800C28—H28B0.9800
C12—H12C0.9800C28—H28C0.9800
C13—C141.534 (3)C29—H290.9500
C13—H13A0.9900C30—C311.533 (3)
C13—H13B0.9900C30—H30A0.9900
C14—C151.526 (3)C30—H30B0.9900
C14—H14A0.9900C31—C321.524 (3)
C14—H14B0.9900C31—H31A0.9900
C16—H160.9500C31—H31B0.9900
N2—N1—C7102.06 (15)N4—N3—C23102.11 (16)
N2—N1—C13101.67 (16)N4—N3—C30102.18 (16)
C7—N1—C13118.14 (17)C23—N3—C30118.16 (17)
C15—N2—N1114.00 (17)C32—N4—N3113.52 (18)
C15—N2—C9133.46 (19)C32—N4—C25133.84 (19)
N1—N2—C9112.53 (16)N3—N4—C25112.64 (17)
C2—C1—C6120.9 (2)C18—C17—C22121.2 (2)
C2—C1—H1119.5C18—C17—H17119.4
C6—C1—H1119.5C22—C17—H17119.4
C1—C2—C3120.2 (2)C17—C18—C19119.8 (2)
C1—C2—H2119.9C17—C18—H18120.1
C3—C2—H2119.9C19—C18—H18120.1
C4—C3—C2119.7 (2)C20—C19—C18119.7 (2)
C4—C3—H3120.2C20—C19—H19120.1
C2—C3—H3120.2C18—C19—H19120.1
C3—C4—C5120.3 (2)C19—C20—C21120.6 (2)
C3—C4—H4119.9C19—C20—H20119.7
C5—C4—H4119.9C21—C20—H20119.7
C6—C5—C4120.2 (2)C20—C21—C22120.1 (2)
C6—C5—H5119.9C20—C21—H21119.9
C4—C5—H5119.9C22—C21—H21119.9
C5—C6—C1118.8 (2)C17—C22—C21118.5 (2)
C5—C6—C7122.7 (2)C17—C22—C23119.19 (19)
C1—C6—C7118.45 (19)C21—C22—C23122.3 (2)
N1—C7—C6113.67 (17)N3—C23—C22113.02 (18)
N1—C7—C8100.75 (17)N3—C23—C24100.72 (17)
C6—C7—C8114.04 (18)C22—C23—C24114.75 (18)
N1—C7—H7109.3N3—C23—H23109.3
C6—C7—H7109.3C22—C23—H23109.3
C8—C7—H7109.3C24—C23—H23109.3
C16—C8—C9110.58 (18)C29—C24—C25110.15 (18)
C16—C8—C7110.91 (18)C29—C24—C23110.62 (18)
C9—C8—C7103.10 (16)C25—C24—C23102.79 (17)
C16—C8—H8110.7C29—C24—H24111.0
C9—C8—H8110.7C25—C24—H24111.0
C7—C8—H8110.7C23—C24—H24111.0
N2—C9—C10111.97 (17)N4—C25—C26111.88 (17)
N2—C9—C8100.87 (16)N4—C25—C24100.99 (17)
C10—C9—C8113.29 (18)C26—C25—C24114.60 (17)
N2—C9—H9110.1N4—C25—H25109.7
C10—C9—H9110.1C26—C25—H25109.7
C8—C9—H9110.1C24—C25—H25109.7
C11—C10—C9112.23 (18)C27—C26—C25113.39 (18)
C11—C10—H10A109.2C27—C26—H26A108.9
C9—C10—H10A109.2C25—C26—H26A108.9
C11—C10—H10B109.2C27—C26—H26B108.9
C9—C10—H10B109.2C25—C26—H26B108.9
H10A—C10—H10B107.9H26A—C26—H26B107.7
C10—C11—C12113.0 (2)C28—C27—C26112.88 (19)
C10—C11—H11A109.0C28—C27—H27A109.0
C12—C11—H11A109.0C26—C27—H27A109.0
C10—C11—H11B109.0C28—C27—H27B109.0
C12—C11—H11B109.0C26—C27—H27B109.0
H11A—C11—H11B107.8H27A—C27—H27B107.8
C11—C12—H12A109.5C27—C28—H28A109.5
C11—C12—H12B109.5C27—C28—H28B109.5
H12A—C12—H12B109.5H28A—C28—H28B109.5
C11—C12—H12C109.5C27—C28—H28C109.5
H12A—C12—H12C109.5H28A—C28—H28C109.5
H12B—C12—H12C109.5H28B—C28—H28C109.5
N1—C13—C14102.53 (17)O3—C29—C24124.2 (2)
N1—C13—H13A111.3O3—C29—H29117.9
C14—C13—H13A111.3C24—C29—H29117.9
N1—C13—H13B111.3N3—C30—C31101.93 (18)
C14—C13—H13B111.3N3—C30—H30A111.4
H13A—C13—H13B109.2C31—C30—H30A111.4
C15—C14—C13102.67 (17)N3—C30—H30B111.4
C15—C14—H14A111.2C31—C30—H30B111.4
C13—C14—H14A111.2H30A—C30—H30B109.2
C15—C14—H14B111.2C32—C31—C30103.10 (18)
C13—C14—H14B111.2C32—C31—H31A111.1
H14A—C14—H14B109.1C30—C31—H31A111.1
O2—C15—N2125.6 (2)C32—C31—H31B111.1
O2—C15—C14128.6 (2)C30—C31—H31B111.1
N2—C15—C14105.74 (19)H31A—C31—H31B109.1
O1—C16—C8124.3 (2)O4—C32—N4125.8 (2)
O1—C16—H16117.9O4—C32—C31128.5 (2)
C8—C16—H16117.9N4—C32—C31105.67 (19)
C7—N1—N2—C15150.02 (17)C23—N3—N4—C32−150.98 (17)
C13—N1—N2—C1527.6 (2)C30—N3—N4—C32−28.3 (2)
C7—N1—N2—C9−29.2 (2)C23—N3—N4—C2528.8 (2)
C13—N1—N2—C9−151.60 (16)C30—N3—N4—C25151.51 (16)
C6—C1—C2—C30.4 (3)C22—C17—C18—C19−0.3 (4)
C1—C2—C3—C4−0.4 (3)C17—C18—C19—C200.7 (4)
C2—C3—C4—C50.1 (3)C18—C19—C20—C21−0.6 (3)
C3—C4—C5—C60.2 (3)C19—C20—C21—C220.2 (3)
C4—C5—C6—C1−0.2 (3)C18—C17—C22—C21−0.1 (3)
C4—C5—C6—C7−177.06 (19)C18—C17—C22—C23−178.5 (2)
C2—C1—C6—C5−0.1 (3)C20—C21—C22—C170.2 (3)
C2—C1—C6—C7176.88 (19)C20—C21—C22—C23178.49 (19)
N2—N1—C7—C6165.37 (16)N4—N3—C23—C22−165.83 (16)
C13—N1—C7—C6−84.2 (2)C30—N3—C23—C2283.1 (2)
N2—N1—C7—C842.96 (19)N4—N3—C23—C24−42.91 (18)
C13—N1—C7—C8153.36 (18)C30—N3—C23—C24−153.98 (17)
C5—C6—C7—N1−23.8 (3)C17—C22—C23—N3−156.73 (19)
C1—C6—C7—N1159.38 (19)C21—C22—C23—N325.0 (3)
C5—C6—C7—C891.0 (2)C17—C22—C23—C2488.5 (2)
C1—C6—C7—C8−85.9 (2)C21—C22—C23—C24−89.7 (2)
N1—C7—C8—C1675.4 (2)N3—C23—C24—C29−74.4 (2)
C6—C7—C8—C16−46.8 (2)C22—C23—C24—C2947.3 (2)
N1—C7—C8—C9−42.98 (19)N3—C23—C24—C2543.14 (19)
C6—C7—C8—C9−165.13 (17)C22—C23—C24—C25164.84 (17)
C15—N2—C9—C10−56.6 (3)C32—N4—C25—C2656.3 (3)
N1—N2—C9—C10122.41 (19)N3—N4—C25—C26−123.46 (19)
C15—N2—C9—C8−177.3 (2)C32—N4—C25—C24178.6 (2)
N1—N2—C9—C81.6 (2)N3—N4—C25—C24−1.1 (2)
C16—C8—C9—N2−93.61 (19)C29—C24—C25—N492.5 (2)
C7—C8—C9—N225.0 (2)C23—C24—C25—N4−25.39 (19)
C16—C8—C9—C10146.57 (18)C29—C24—C25—C26−147.07 (19)
C7—C8—C9—C10−94.83 (19)C23—C24—C25—C2695.0 (2)
N2—C9—C10—C11169.09 (18)N4—C25—C26—C27−174.41 (18)
C8—C9—C10—C11−77.6 (2)C24—C25—C26—C2771.4 (2)
C9—C10—C11—C12172.6 (2)C25—C26—C27—C28179.12 (19)
N2—N1—C13—C14−35.4 (2)C25—C24—C29—O3125.5 (2)
C7—N1—C13—C14−146.05 (18)C23—C24—C29—O3−121.5 (2)
N1—C13—C14—C1532.4 (2)N4—N3—C30—C3135.74 (19)
N1—N2—C15—O2172.3 (2)C23—N3—C30—C31146.78 (18)
C9—N2—C15—O2−8.8 (4)N3—C30—C31—C32−32.3 (2)
N1—N2—C15—C14−6.5 (2)N3—N4—C32—O4−171.5 (2)
C9—N2—C15—C14172.5 (2)C25—N4—C32—O48.7 (4)
C13—C14—C15—O2164.7 (2)N3—N4—C32—C317.1 (2)
C13—C14—C15—N2−16.6 (2)C25—N4—C32—C31−172.7 (2)
C9—C8—C16—O1−124.8 (2)C30—C31—C32—O4−165.3 (2)
C7—C8—C16—O1121.5 (2)C30—C31—C32—N416.2 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2144).

References

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