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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1576.
Published online 2010 June 5. doi:  10.1107/S1600536810018714
PMCID: PMC3007067

(S)-tert-Butyl 3-(3-phenyl-1,2,4-oxa­diazol-5-yl)piperidine-1-carboxyl­ate

Abstract

The title compound, C18H23N3O3, crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The phenyl ring and the 1,2,4-oxadiazole ring are inclined to one another by 19.9 (3)° in mol­ecule A and 7.3 (3)° in mol­ecule B. The absolute structure of the title compound was referred to the transfered chiral center (S) of one of the starting reacta­nts. In the crystal, A mol­ecules are linked by C—H(...)N inter­actions involving the two oxadiazole N atoms.

Related literature

For the oxadiazole nucleus as a core structural unit of various muscarinic agonists, see: Orlek & Blaney (1991 [triangle]). For benzodiazepine receptor partial agonists, see: Watjen & Baker (1989 [triangle]). For dopamine transporters, see: Gray & Abrahm (1993 [triangle]). For 5-HT agonists, see: Swain & Baker (1991 [triangle]). For inhibitors of HIV, see: Matthew et al. (2007 [triangle]). For GABAA receptor agonists, see: Michaela & Holger (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1576-scheme1.jpg

Experimental

Crystal data

  • C18H23N3O3
  • M r = 329.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1576-efi1.jpg
  • a = 6.464 (3) Å
  • b = 15.515 (8) Å
  • c = 17.847 (9) Å
  • β = 99.880 (7)°
  • V = 1763.2 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.24 × 0.15 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008 [triangle]) T min = 0.980, T max = 0.990
  • 7378 measured reflections
  • 3258 independent reflections
  • 2520 reflections with I > 2σ(I)
  • R int = 0.073

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.198
  • S = 1.01
  • 3258 reflections
  • 440 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; 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: SHELXL97 and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810018714/su2175sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018714/su2175Isup2.hkl

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

supplementary crystallographic information

Comment

The oxadiazole nucleus is a well studied pharmacophoric scaffold that has emerged as a core structural unit of various muscarinic agonists (Orlek & Blaney, 1991), benzodiazepine receptor partial agonists (Watjen & Baker, 1989), dopamine transporters (Gray & Abrahm, 1993), 5-HT agonists (Swain & Baker, 1991), inhibitors of HIV (Matthew, 2007), and GABAA receptor agonists (Michaela & Holger,2008). Among the oxadiazoles, 1,2,4-oxadiazole derivatives have gained importance in medicinal chemistry. The interest in five-membered systems containing one oxygen and two nitrogen atoms (positions 1, 2, and 4) is due to the occurrence of 1,2,4-oxadiazoles in biological activite compounds and natural products. In spite of extensive investigations, there are few studies on the crystal structures of oxadiazol-piperidines. Herein, we report on the crystal structure of the title compound, a new oxadiazol-piperidine. It can be reacted with acid, sulfonlchloride and chloride, followed by deprotection of the protective group, to give many usefull compounds.

The title compound crystallized in the chiral monoclinic space group P21, with two independent molecules (A and B) in the asymmetric unit (Fig. 1). It was obtained from a chiral source, hence its absolute structure, (S), was confirmed by the transfered chiral center; atom C9 in molecule A and atom C27 in molecule B (Fig. 1). The bond distances in the two molecules are very similar and close to normal values (Allen et al., 1987). The two molecules differ in the orientation of the phenyl ring with respect to the oxadiazole mean plane. In molecule A this dihedral angle is 19.9 (3)°, while in molecule B it is only 7.3 (3)°. In both molecules the piperidine ring has a chair conformation.

In the crystal symmetry related A molecules are linked via C-H···N interactions (see Table 1 and Fig. 2 for details).

Experimental

A suspension of hydroxylamine hydrochloride (4.09 g), potassium carbonate (2.76 g), benzonitrile (1.03 g) in absolute ethanol (200 mL) was heated at reflux for 10 h. After the reaction was completed, monitored by TLC, the mixture was cooled, filtered to remove inorganic salts, and concentrated under vacuum. The residue was purified by column chromatography, by use of a gradient elution of dichloromethane to 40% acetone in dichloromethane, to give (E)-N-hydroxybenzamidine (1.36g). 1H NMR (300 MHz, DMSO-d6): 9.59 (s, 1H), 7.62-7.67 (m, 2H), 7.32-7.37 (m, 3H), 5.77 (s, 2H); EI (M+) 136 A mixture of (S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (1.15 g) in absolute THF (50 mL), isobutyl carbonochloridate (5ml) and trimethylamine (2ml) were mixted together and stirred for 30min at rt, followed by slow dropwise addition of (E)-N-Hydroxy-benzamidine (1.36g) in THF (15mL). After the reaction was completed, monitored by TLC, the mixture was injected into n-Bu4NF (1 M in THF, 3 mL), warmed to reflux and was stirred for 24 h. After this reaction was completed, monitored by TLC, the mixture was poured into EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography by use of a gradient elution of EtOAc/hexanes. The material was crystallized from EtOH to give the title compound as a white solid. Colourless-rod-like crystals, suitable for X-ray analysis, were obtained by recrystallization from EtOH. 1H NMR (300MHz, CDCl3): 8.05,-8.08 (m, 2H), 7.43-7.48 (m, 3H), 3.95 (d, 1H, J=8.4 Hz), 3.12-3.17 (m, 1H), 3.98 (t, 1H, J=12.6 Hz), 2.42 (d, 1H, J=12.6 Hz), 1.86 (t, 2H, J=12.6 Hz), 1.55-1.65 (m, 1H), 1.45 (s, 9H), 0.83-0.92 (m, 2H); ESI (M++23) 352.

Refinement

In the final cycles of refinement, in the absence of significant anomalous scattering effects, 4120 Friedel pairs were merged and Δf " set to zero. The H-atoms could all be located in difference Fourier maps. In the final cycles of refinment they were placed in calculated positions and treated as riding atoms: C—H 0.93, 0.96, 0.97 and 0.98 Å, for H-methine, H-methyl, H-methylene and H-aromtic, respectively, with Uiso(H) = k × Ueq(C), where k = 1.5 for H-methyl and = 1.2 for all other H-atoms.

Figures

Fig. 1.
The molecular structure of the two independent molecules (A and B) of the title compound, with atom labels and 30% probability displacement ellipsoids.
Fig. 2.
A view along the a-axis of the crystal packing of the title compound (Molecule A is black; Molecule B is red; C-H···N interactions are shown as dotted lines; see Table 1 for details).

Crystal data

C18H23N3O3F(000) = 704
Mr = 329.39Dx = 1.241 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 818 reflections
a = 6.464 (3) Åθ = 2.7–23.3°
b = 15.515 (8) ŵ = 0.09 mm1
c = 17.847 (9) ÅT = 293 K
β = 99.880 (7)°Rod, colourless
V = 1763.2 (15) Å30.24 × 0.15 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3258 independent reflections
Radiation source: fine-focus sealed tube2520 reflections with I > 2σ(I)
graphiteRint = 0.073
phi and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)h = −7→7
Tmin = 0.980, Tmax = 0.990k = −18→16
7378 measured reflectionsl = −21→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.073H-atom parameters constrained
wR(F2) = 0.198w = 1/[σ2(Fo2) + (0.1416P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3258 reflectionsΔρmax = 0.29 e Å3
440 parametersΔρmin = −0.44 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (4)

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 esds are taken into account in the estimation of distances, angles and torsion angles
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 > 2sigma(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
O10.4355 (6)0.9886 (3)0.68689 (18)0.0605 (12)
O21.1738 (6)0.7663 (3)0.79331 (18)0.0644 (15)
O31.2986 (7)0.7271 (3)0.6870 (2)0.0747 (16)
N10.5574 (6)0.9308 (3)0.7976 (2)0.0536 (14)
N20.3265 (7)1.0282 (3)0.7402 (2)0.0603 (17)
N31.0660 (7)0.8361 (3)0.6855 (2)0.0626 (16)
C10.3287 (8)1.0093 (3)0.8751 (3)0.0524 (19)
C20.1341 (9)1.0467 (4)0.8740 (3)0.062 (2)
C30.0626 (11)1.0639 (4)0.9411 (3)0.070 (2)
C40.1837 (11)1.0425 (4)1.0097 (3)0.072 (2)
C50.3769 (12)1.0042 (4)1.0113 (3)0.079 (2)
C60.4488 (9)0.9868 (4)0.9447 (3)0.067 (2)
C70.4026 (7)0.9904 (3)0.8048 (3)0.0496 (17)
C80.5670 (7)0.9310 (3)0.7267 (3)0.0496 (17)
C90.6996 (8)0.8775 (4)0.6851 (3)0.0529 (17)
C100.6740 (9)0.8942 (5)0.6013 (3)0.068 (2)
C110.8260 (9)0.8384 (5)0.5657 (3)0.067 (2)
C121.0481 (9)0.8513 (4)0.6046 (3)0.061 (2)
C130.9262 (8)0.8882 (4)0.7234 (2)0.0584 (18)
C141.1864 (8)0.7715 (4)0.7210 (3)0.0542 (17)
C151.2965 (10)0.7014 (4)0.8439 (3)0.067 (2)
C161.2285 (14)0.7220 (6)0.9186 (3)0.106 (3)
C171.2262 (15)0.6118 (5)0.8167 (4)0.102 (3)
C181.5243 (11)0.7145 (5)0.8480 (4)0.086 (3)
O40.6093 (6)0.1946 (3)0.82130 (18)0.0652 (13)
O5−0.2882 (7)0.4596 (3)0.8012 (2)0.0755 (16)
O6−0.1493 (6)0.4210 (3)0.69793 (18)0.0678 (15)
N40.7414 (7)0.1666 (4)0.7705 (2)0.0672 (19)
N50.4557 (7)0.2334 (3)0.7072 (2)0.0514 (14)
N60.0024 (7)0.3759 (3)0.8124 (2)0.0583 (15)
C190.7234 (8)0.1768 (3)0.6348 (3)0.0502 (17)
C200.9211 (9)0.1437 (4)0.6355 (3)0.0614 (17)
C210.9925 (10)0.1274 (4)0.5684 (3)0.072 (2)
C220.8669 (11)0.1471 (4)0.4995 (3)0.075 (3)
C230.6724 (10)0.1798 (4)0.4977 (3)0.070 (2)
C240.5980 (9)0.1963 (4)0.5641 (3)0.0617 (19)
C250.6435 (8)0.1934 (3)0.7043 (2)0.0489 (17)
C260.4423 (8)0.2318 (3)0.7778 (3)0.0500 (16)
C270.2658 (9)0.2633 (3)0.8154 (3)0.0514 (16)
C280.3205 (9)0.2705 (4)0.9012 (3)0.0626 (19)
C290.1270 (10)0.2999 (4)0.9314 (3)0.069 (2)
C300.0361 (10)0.3818 (4)0.8946 (3)0.0642 (19)
C310.1823 (9)0.3471 (4)0.7790 (3)0.0569 (19)
C32−0.1542 (9)0.4222 (4)0.7715 (3)0.0570 (19)
C33−0.2846 (9)0.4763 (4)0.6425 (3)0.0621 (19)
C34−0.2377 (13)0.5693 (5)0.6619 (4)0.088 (3)
C35−0.2098 (11)0.4529 (5)0.5692 (3)0.083 (3)
C36−0.5115 (10)0.4536 (5)0.6379 (4)0.081 (3)
H2A0.050801.060500.827700.0740*
H3A−0.067501.089900.939900.0850*
H4A0.135401.053801.054900.0870*
H5A0.459000.990001.057700.0950*
H6A0.578000.959800.946200.0800*
H9A0.661300.817200.691600.0640*
H10A0.700800.954600.592600.0820*
H10B0.530800.881500.577600.0820*
H11A0.788200.778200.569200.0800*
H11B0.814500.852800.512300.0800*
H12A1.139500.811900.583500.0730*
H12B1.092100.909700.595900.0730*
H13A0.965900.948400.721900.0700*
H13B0.940700.871000.776300.0700*
H16A1.265100.780500.932500.1590*
H16B1.297900.683900.957200.1590*
H16C1.079200.714800.913600.1590*
H17A1.262400.601900.767400.1530*
H17B1.076900.607000.813500.1530*
H17C1.295000.569800.851900.1530*
H18A1.555700.775000.852400.1300*
H18B1.566500.692200.802700.1300*
H18C1.599000.684800.891600.1300*
H20A1.007500.132200.681700.0740*
H21A1.124600.103300.569300.0860*
H22A0.916700.137700.454300.0900*
H23A0.587800.191400.451200.0840*
H24A0.465400.220300.562400.0740*
H27A0.152300.220900.804300.0620*
H28A0.366900.215100.923000.0750*
H28B0.433300.311800.915100.0750*
H29A0.021500.254800.922600.0830*
H29B0.163200.308700.985800.0830*
H30A−0.096500.393900.911000.0770*
H30B0.130900.429300.910900.0770*
H31A0.291700.390500.786900.0680*
H31B0.139500.338900.724600.0680*
H34A−0.290800.583800.707400.1320*
H34B−0.303700.605100.620800.1320*
H34C−0.088600.578400.670100.1320*
H35A−0.061400.462900.574700.1240*
H35B−0.281900.487800.528500.1240*
H35C−0.238800.393200.557900.1240*
H36A−0.559000.472500.683300.1220*
H36B−0.528500.392300.632800.1220*
H36C−0.592700.481500.594500.1220*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.058 (2)0.070 (2)0.052 (2)0.0050 (18)0.0049 (16)0.0100 (17)
O20.071 (3)0.081 (3)0.0403 (19)0.015 (2)0.0071 (16)0.0061 (17)
O30.083 (3)0.089 (3)0.053 (2)0.020 (2)0.0144 (18)0.0008 (19)
N10.052 (3)0.056 (2)0.051 (2)0.006 (2)0.0039 (17)0.0042 (19)
N20.052 (3)0.069 (3)0.060 (3)0.008 (2)0.0096 (19)0.011 (2)
N30.066 (3)0.085 (3)0.036 (2)0.019 (2)0.0064 (17)0.002 (2)
C10.060 (4)0.046 (3)0.050 (3)−0.004 (2)0.006 (2)0.003 (2)
C20.055 (4)0.055 (3)0.073 (4)−0.002 (3)0.007 (2)0.005 (3)
C30.084 (5)0.056 (3)0.076 (4)0.002 (3)0.028 (3)−0.005 (3)
C40.106 (5)0.057 (3)0.059 (3)−0.010 (3)0.029 (3)−0.006 (3)
C50.097 (5)0.078 (4)0.058 (3)−0.006 (4)0.002 (3)0.000 (3)
C60.066 (4)0.069 (4)0.062 (3)0.000 (3)0.002 (3)−0.001 (3)
C70.035 (3)0.052 (3)0.060 (3)−0.006 (2)0.003 (2)0.002 (2)
C80.037 (3)0.055 (3)0.054 (3)−0.003 (2)−0.0004 (19)0.004 (2)
C90.044 (3)0.058 (3)0.056 (3)−0.003 (2)0.007 (2)0.001 (2)
C100.048 (3)0.103 (5)0.048 (3)−0.003 (3)−0.007 (2)0.002 (3)
C110.066 (4)0.097 (4)0.036 (3)−0.003 (3)0.005 (2)0.002 (3)
C120.062 (4)0.078 (4)0.044 (3)0.005 (3)0.012 (2)0.008 (2)
C130.058 (3)0.078 (4)0.037 (2)0.013 (3)0.002 (2)−0.002 (2)
C140.057 (3)0.062 (3)0.042 (3)−0.002 (3)0.004 (2)−0.001 (2)
C150.074 (4)0.069 (4)0.053 (3)0.006 (3)−0.002 (2)0.019 (3)
C160.128 (7)0.137 (7)0.048 (3)0.004 (6)0.004 (4)0.024 (4)
C170.127 (7)0.081 (5)0.087 (5)−0.020 (5)−0.011 (4)0.022 (4)
C180.074 (5)0.083 (5)0.093 (4)0.003 (3)−0.012 (3)0.022 (4)
O40.052 (2)0.094 (3)0.0467 (18)0.017 (2)0.0005 (14)0.0030 (18)
O50.079 (3)0.100 (3)0.049 (2)0.026 (2)0.0150 (19)0.003 (2)
O60.072 (3)0.090 (3)0.0415 (18)0.026 (2)0.0104 (16)0.0123 (18)
N40.045 (3)0.099 (4)0.056 (3)0.016 (2)0.0039 (18)0.004 (2)
N50.054 (3)0.057 (2)0.042 (2)0.008 (2)0.0049 (16)0.0065 (17)
N60.073 (3)0.067 (3)0.0359 (19)0.017 (2)0.0124 (18)0.0042 (19)
C190.042 (3)0.053 (3)0.053 (3)−0.004 (2)0.001 (2)0.002 (2)
C200.055 (3)0.067 (3)0.061 (3)0.006 (3)0.007 (2)0.003 (3)
C210.060 (4)0.081 (4)0.075 (4)0.010 (3)0.015 (3)−0.005 (3)
C220.083 (5)0.081 (4)0.066 (4)0.002 (3)0.027 (3)−0.007 (3)
C230.073 (4)0.080 (4)0.055 (3)−0.008 (3)0.006 (3)0.001 (3)
C240.059 (3)0.076 (4)0.048 (3)0.004 (3)0.003 (2)0.004 (3)
C250.048 (3)0.050 (3)0.046 (3)−0.003 (2)0.0002 (19)0.005 (2)
C260.050 (3)0.051 (3)0.046 (2)0.006 (2)−0.0001 (19)0.001 (2)
C270.060 (3)0.055 (3)0.038 (2)0.007 (2)0.005 (2)0.001 (2)
C280.071 (4)0.071 (3)0.044 (3)0.010 (3)0.005 (2)0.006 (2)
C290.089 (4)0.083 (4)0.037 (3)0.014 (3)0.014 (3)0.014 (2)
C300.084 (4)0.070 (3)0.040 (3)0.007 (3)0.015 (2)0.002 (2)
C310.064 (4)0.065 (3)0.043 (3)0.011 (2)0.013 (2)0.009 (2)
C320.070 (4)0.059 (3)0.042 (3)0.009 (3)0.010 (2)0.000 (2)
C330.069 (4)0.071 (3)0.042 (3)0.006 (3)−0.003 (2)0.006 (2)
C340.108 (6)0.076 (4)0.075 (4)−0.009 (4)0.000 (4)0.008 (3)
C350.086 (5)0.111 (6)0.048 (3)0.005 (4)0.004 (3)0.007 (3)
C360.072 (5)0.092 (5)0.073 (4)−0.002 (3)−0.006 (3)0.017 (3)

Geometric parameters (Å, °)

O1—N21.417 (6)C13—H13A0.9700
O1—C81.349 (6)C13—H13B0.9700
O2—C141.309 (6)C16—H16A0.9600
O2—C151.487 (7)C16—H16B0.9600
O3—C141.233 (7)C16—H16C0.9600
O4—C261.347 (6)C17—H17C0.9600
O4—N41.416 (6)C17—H17A0.9600
O5—C321.235 (7)C17—H17B0.9600
O6—C331.477 (7)C18—H18B0.9600
O6—C321.319 (6)C18—H18C0.9600
N1—C71.385 (6)C18—H18A0.9600
N1—C81.278 (6)C19—C201.375 (8)
N2—C71.312 (6)C19—C241.411 (8)
N3—C131.462 (7)C19—C251.446 (7)
N3—C141.357 (7)C20—C211.379 (8)
N3—C121.448 (6)C21—C221.386 (8)
N4—C251.309 (6)C22—C231.351 (10)
N5—C251.372 (7)C23—C241.377 (8)
N5—C261.278 (6)C26—C271.501 (8)
N6—C311.465 (7)C27—C281.515 (8)
N6—C321.349 (7)C27—C311.511 (8)
N6—C301.449 (6)C28—C291.515 (9)
C1—C71.447 (7)C29—C301.503 (9)
C1—C21.382 (8)C33—C341.503 (10)
C1—C61.392 (8)C33—C351.515 (8)
C2—C31.382 (8)C33—C361.497 (9)
C3—C41.376 (8)C20—H20A0.9300
C4—C51.379 (10)C21—H21A0.9300
C5—C61.375 (8)C22—H22A0.9300
C8—C91.481 (7)C23—H23A0.9300
C9—C131.516 (7)C24—H24A0.9300
C9—C101.499 (8)C27—H27A0.9800
C10—C111.527 (9)C28—H28A0.9700
C11—C121.497 (8)C28—H28B0.9700
C15—C171.516 (10)C29—H29A0.9700
C15—C161.508 (9)C29—H29B0.9700
C15—C181.476 (10)C30—H30A0.9700
C2—H2A0.9300C30—H30B0.9700
C3—H3A0.9300C31—H31A0.9700
C4—H4A0.9300C31—H31B0.9700
C5—H5A0.9300C34—H34A0.9600
C6—H6A0.9300C34—H34B0.9600
C9—H9A0.9800C34—H34C0.9600
C10—H10A0.9700C35—H35A0.9600
C10—H10B0.9700C35—H35B0.9600
C11—H11A0.9700C35—H35C0.9600
C11—H11B0.9700C36—H36A0.9600
C12—H12B0.9700C36—H36B0.9600
C12—H12A0.9700C36—H36C0.9600
N2—O1—C8105.9 (3)H17B—C17—H17C110.00
C14—O2—C15121.5 (5)C15—C18—H18A109.00
N4—O4—C26105.9 (4)C15—C18—H18B109.00
C32—O6—C33123.1 (5)C15—C18—H18C109.00
C7—N1—C8104.4 (4)H18A—C18—H18B110.00
O1—N2—C7104.0 (4)H18A—C18—H18C109.00
C12—N3—C14121.8 (5)H18B—C18—H18C109.00
C13—N3—C14122.9 (4)C20—C19—C24118.6 (5)
C12—N3—C13114.9 (4)C20—C19—C25121.8 (5)
O4—N4—C25103.3 (4)C24—C19—C25119.6 (5)
C25—N5—C26103.8 (4)C19—C20—C21120.6 (5)
C30—N6—C32118.9 (5)C20—C21—C22119.8 (6)
C31—N6—C32121.1 (4)C21—C22—C23120.3 (5)
C30—N6—C31116.1 (4)C22—C23—C24120.7 (5)
C2—C1—C6119.0 (5)C19—C24—C23119.9 (5)
C2—C1—C7120.5 (5)N4—C25—N5113.8 (4)
C6—C1—C7120.4 (5)N4—C25—C19122.0 (5)
C1—C2—C3120.5 (5)N5—C25—C19124.2 (4)
C2—C3—C4120.1 (6)O4—C26—N5113.2 (5)
C3—C4—C5119.8 (5)O4—C26—C27118.5 (4)
C4—C5—C6120.4 (5)N5—C26—C27128.3 (5)
C1—C6—C5120.2 (6)C26—C27—C28114.4 (5)
N2—C7—C1122.8 (4)C26—C27—C31109.3 (4)
N1—C7—N2112.7 (4)C28—C27—C31112.0 (4)
N1—C7—C1124.6 (4)C27—C28—C29108.5 (5)
O1—C8—N1113.0 (4)C28—C29—C30112.6 (5)
O1—C8—C9118.3 (4)N6—C30—C29111.6 (5)
N1—C8—C9128.8 (5)N6—C31—C27109.7 (4)
C8—C9—C10115.4 (5)O5—C32—O6124.9 (5)
C8—C9—C13108.1 (4)O5—C32—N6122.3 (5)
C10—C9—C13111.3 (4)O6—C32—N6112.8 (5)
C9—C10—C11110.4 (5)O6—C33—C34109.3 (5)
C10—C11—C12111.4 (5)O6—C33—C35101.5 (5)
N3—C12—C11110.3 (5)O6—C33—C36111.2 (5)
N3—C13—C9110.9 (4)C34—C33—C35110.3 (5)
O3—C14—N3121.4 (5)C34—C33—C36113.3 (6)
O2—C14—N3112.2 (5)C35—C33—C36110.6 (5)
O2—C14—O3126.3 (5)C19—C20—H20A120.00
C16—C15—C17111.1 (6)C21—C20—H20A120.00
O2—C15—C18111.1 (5)C20—C21—H21A120.00
O2—C15—C17109.1 (5)C22—C21—H21A120.00
O2—C15—C16100.8 (5)C21—C22—H22A120.00
C16—C15—C18111.5 (6)C23—C22—H22A120.00
C17—C15—C18112.6 (6)C22—C23—H23A120.00
C1—C2—H2A120.00C24—C23—H23A120.00
C3—C2—H2A120.00C19—C24—H24A120.00
C2—C3—H3A120.00C23—C24—H24A120.00
C4—C3—H3A120.00C26—C27—H27A107.00
C3—C4—H4A120.00C28—C27—H27A107.00
C5—C4—H4A120.00C31—C27—H27A107.00
C6—C5—H5A120.00C27—C28—H28A110.00
C4—C5—H5A120.00C27—C28—H28B110.00
C1—C6—H6A120.00C29—C28—H28A110.00
C5—C6—H6A120.00C29—C28—H28B110.00
C13—C9—H9A107.00H28A—C28—H28B108.00
C8—C9—H9A107.00C28—C29—H29A109.00
C10—C9—H9A107.00C28—C29—H29B109.00
C9—C10—H10A110.00C30—C29—H29A109.00
C9—C10—H10B110.00C30—C29—H29B109.00
C11—C10—H10A110.00H29A—C29—H29B108.00
C11—C10—H10B110.00N6—C30—H30A109.00
H10A—C10—H10B108.00N6—C30—H30B109.00
C10—C11—H11A109.00C29—C30—H30A109.00
C10—C11—H11B109.00C29—C30—H30B109.00
C12—C11—H11B109.00H30A—C30—H30B108.00
H11A—C11—H11B108.00N6—C31—H31A110.00
C12—C11—H11A109.00N6—C31—H31B110.00
H12A—C12—H12B108.00C27—C31—H31A110.00
C11—C12—H12B110.00C27—C31—H31B110.00
N3—C12—H12A110.00H31A—C31—H31B108.00
N3—C12—H12B110.00C33—C34—H34A109.00
C11—C12—H12A110.00C33—C34—H34B110.00
N3—C13—H13A109.00C33—C34—H34C110.00
N3—C13—H13B110.00H34A—C34—H34B110.00
C9—C13—H13A109.00H34A—C34—H34C109.00
C9—C13—H13B109.00H34B—C34—H34C110.00
H13A—C13—H13B108.00C33—C35—H35A110.00
C15—C16—H16A109.00C33—C35—H35B109.00
C15—C16—H16B109.00C33—C35—H35C109.00
C15—C16—H16C110.00H35A—C35—H35B109.00
H16B—C16—H16C110.00H35A—C35—H35C109.00
H16A—C16—H16B109.00H35B—C35—H35C109.00
H16A—C16—H16C109.00C33—C36—H36A110.00
H17A—C17—H17C109.00C33—C36—H36B109.00
C15—C17—H17A109.00C33—C36—H36C109.00
C15—C17—H17B109.00H36A—C36—H36B110.00
C15—C17—H17C109.00H36A—C36—H36C109.00
H17A—C17—H17B109.00H36B—C36—H36C109.00
N2—O1—C8—N1−1.4 (6)C2—C1—C7—N220.5 (8)
N2—O1—C8—C9178.5 (4)C6—C1—C2—C32.0 (9)
C8—O1—N2—C7−0.3 (5)C7—C1—C2—C3179.3 (5)
C15—O2—C14—O3−1.6 (9)C2—C1—C6—C5−2.0 (9)
C15—O2—C14—N3−178.6 (5)C7—C1—C6—C5−179.4 (5)
C14—O2—C15—C17−63.1 (7)C2—C1—C7—N1−158.8 (5)
C14—O2—C15—C1861.6 (7)C6—C1—C7—N2−162.2 (5)
C14—O2—C15—C16179.9 (6)C6—C1—C7—N118.5 (8)
N4—O4—C26—C27176.2 (4)C1—C2—C3—C4−1.1 (9)
N4—O4—C26—N5−2.2 (6)C2—C3—C4—C50.3 (10)
C26—O4—N4—C252.7 (6)C3—C4—C5—C6−0.4 (10)
C33—O6—C32—N6−171.1 (5)C4—C5—C6—C11.3 (9)
C32—O6—C33—C36−65.0 (7)N1—C8—C9—C10−179.6 (5)
C32—O6—C33—C3460.9 (7)O1—C8—C9—C13125.9 (5)
C33—O6—C32—O510.3 (9)O1—C8—C9—C100.6 (7)
C32—O6—C33—C35177.4 (5)N1—C8—C9—C13−54.3 (7)
C7—N1—C8—O12.3 (6)C8—C9—C10—C11177.3 (5)
C8—N1—C7—N2−2.5 (6)C13—C9—C10—C1153.6 (7)
C8—N1—C7—C1176.8 (5)C8—C9—C13—N3179.4 (4)
C7—N1—C8—C9−177.6 (5)C10—C9—C13—N3−52.9 (7)
O1—N2—C7—N11.7 (5)C9—C10—C11—C12−55.1 (7)
O1—N2—C7—C1−177.7 (4)C10—C11—C12—N354.9 (7)
C13—N3—C14—O3178.0 (5)C24—C19—C20—C21−2.0 (8)
C13—N3—C12—C11−55.9 (7)C25—C19—C20—C21179.1 (5)
C14—N3—C12—C11117.0 (6)C20—C19—C24—C231.8 (8)
C12—N3—C13—C954.8 (6)C25—C19—C24—C23−179.3 (5)
C14—N3—C13—C9−118.0 (5)C20—C19—C25—N4−10.0 (8)
C12—N3—C14—O2−177.1 (5)C20—C19—C25—N5173.9 (5)
C12—N3—C14—O35.7 (8)C24—C19—C25—N4171.1 (5)
C13—N3—C14—O2−4.8 (7)C24—C19—C25—N5−4.9 (8)
O4—N4—C25—N5−2.4 (6)C19—C20—C21—C222.1 (9)
O4—N4—C25—C19−178.8 (4)C20—C21—C22—C23−2.0 (10)
C26—N5—C25—C19177.4 (5)C21—C22—C23—C241.8 (10)
C25—N5—C26—O40.8 (6)C22—C23—C24—C19−1.7 (9)
C26—N5—C25—N41.1 (6)O4—C26—C27—C2815.2 (7)
C25—N5—C26—C27−177.4 (5)O4—C26—C27—C31141.7 (5)
C32—N6—C30—C29150.6 (5)N5—C26—C27—C28−166.7 (5)
C31—N6—C30—C29−51.5 (7)N5—C26—C27—C31−40.2 (7)
C32—N6—C31—C27−149.7 (5)C26—C27—C28—C29−178.1 (4)
C30—N6—C32—O5−10.6 (9)C31—C27—C28—C2956.8 (6)
C30—N6—C32—O6170.8 (5)C26—C27—C31—N6176.9 (4)
C31—N6—C32—O5−167.4 (6)C28—C27—C31—N6−55.3 (6)
C31—N6—C32—O614.0 (8)C27—C28—C29—C30−54.6 (6)
C30—N6—C31—C2752.9 (6)C28—C29—C30—N651.8 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13A···N2i0.972.613.352 (7)133
C18—H18A···N1i0.962.613.490 (9)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2175).

References

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