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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2328.
Published online 2008 November 13. doi:  10.1107/S1600536808036830
PMCID: PMC2959826

r-2,c-6-Bis(4-methoxy­phen­yl)-c-3,t-3-dimethyl­piperidin-4-one

Abstract

The asymmetric unit of the title compound, C21H25NO3, contains two crystallographically independent mol­ecules (A and B). In both mol­ecules, the piperidine ring adopts a chair conformation, with the methoxy­phenyl rings attached equatorially. The dihedral angle between the two benzene rings in mol­ecule A is 73.79 (8)°; the corresponding value in mol­ecule B is 77.71 (8)°. The mol­ecules are linked by N—H(...)O hydrogen bonds. In addition, C—H(...)π inter­actions are also found in the crystal structure.

Related literature

For a related crystal structure, see: Gayathri et al. (2008 [triangle]). For the biological and pharmacological activities of piperidones, see: Dimmock et al. (1990 [triangle]); Mutus et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2328-scheme1.jpg

Experimental

Crystal data

  • C21H25NO3
  • M r = 339.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2328-efi1.jpg
  • a = 5.9772 (2) Å
  • b = 23.0858 (8) Å
  • c = 26.7611 (8) Å
  • β = 93.543 (3)°
  • V = 3685.7 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 200 (2) K
  • 0.47 × 0.39 × 0.21 mm

Data collection

  • Oxford Diffraction Gemini R diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.866, T max = 1.000 (expected range = 0.852–0.983)
  • 31849 measured reflections
  • 12080 independent reflections
  • 3437 reflections with I > 2σ(I)
  • R int = 0.087

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.100
  • S = 0.74
  • 12080 reflections
  • 459 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; 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]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036830/wn2288sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036830/wn2288Isup2.hkl

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

Acknowledgments

AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007]. RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

supplementary crystallographic information

Comment

2,6-Disubstituted 4-piperidones have various biological and pharmacological activities (Dimmock et al., 1990; Mutus et al., 1989). The crystal structure of r-2,c-6-bis(4-chlorophenyl)-t-3-isopropyl-1-nitrosopiperidin-4-one has been reported, in which the piperidine ring adopts a chair conformation (Gayathri et al., 2008).

The asymmetric unit of the title compound, C21H25NO3, contains two crystallographically independent molecules A and B. In both molecules, the piperidine ring adopts a chair conformation, with the methoxyphenyl rings and one of the methyl groups attached equatorially. The dihedral angle between the two benzene rings in molecule A is 73.79 (8)°; the corresponding value in molecule B is 77.71 (8)°. Both molecules are nearly identical, the r.m.s deviation of an overlay of all non-hydrogen atoms being 0.127 Å. The molecules are linked by N1A—H1A···O4B hydrogen bonds. Furthermore, C25B—H25B···π, C32A—H32B···π and C5B—H52B···π interactions are also found in the crystal structure (Fig. 3, Table 1).

Experimental

Anisaldehyde (24.2 ml, 0.20 mol), 3-methyl-2-butanone (10.7 ml, 0.10 mol) and ammonium acetate (7.7 g, 0.10 mol) were dissolved in 80 ml of distilled ethanol and heated over a boiling water bath, with shaking until a yellow colour developed, which changed to orange. The solution was left undisturbed for 14 h. The precipitated solid was filtered and purified by recrystallization from ethanol. The yield obtained was 72.4% (24.6 g).

Refinement

Atoms H1A at N1A and H1B at N1B were located in a difference Fourier map and refined isotropically; N1A—H1A = 0.92 (2) Å and N1B—H1B = 0.87 (2) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95, 0.98, 0.99 and 1.00 Å for Csp2, methyl, methylene and methine C, respectively; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the independent molecule A, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for H atoms).
Fig. 2.
The molecular structure of the independent molecule B, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for H atoms).
Fig. 3.
The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C21H25NO3F000 = 1456
Mr = 339.42Dx = 1.223 Mg m3
Monoclinic, P21/cMelting point: 344(1) K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 5.9772 (2) ÅCell parameters from 4399 reflections
b = 23.0858 (8) Åθ = 4.6–32.5º
c = 26.7611 (8) ŵ = 0.08 mm1
β = 93.543 (3)ºT = 200 (2) K
V = 3685.7 (2) Å3Rectangular prism, colourless
Z = 80.47 × 0.39 × 0.21 mm

Data collection

Oxford Diffraction R Gemini diffractometer12080 independent reflections
Radiation source: fine-focus sealed tube3437 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.087
Detector resolution: 10.5081 pixels mm-1θmax = 32.6º
T = 200(2) Kθmin = 4.6º
[var phi] and ω scansh = −8→8
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)k = −34→34
Tmin = 0.866, Tmax = 1.000l = −40→36
31849 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)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100  w = 1/[σ2(Fo2) + (0.0352P)2] where P = (Fo2 + 2Fc2)/3
S = 0.74(Δ/σ)max = 0.001
12080 reflectionsΔρmax = 0.19 e Å3
459 parametersΔρmin = −0.19 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 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 > 2σ(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
O2A0.34797 (17)0.45889 (5)0.11995 (4)0.0454 (4)
O4A0.99167 (18)0.16935 (5)−0.03347 (4)0.0541 (5)
O6A1.13775 (19)0.04235 (5)0.27582 (4)0.0563 (5)
N1A0.8561 (2)0.21976 (6)0.10498 (5)0.0343 (5)
C2A0.8410 (2)0.26156 (7)0.06365 (5)0.0331 (5)
C3A0.7590 (2)0.23032 (7)0.01421 (5)0.0364 (6)
C4A0.9137 (3)0.17926 (8)0.00670 (6)0.0410 (6)
C5A0.9674 (3)0.14121 (7)0.05153 (6)0.0449 (6)
C6A1.0314 (3)0.17631 (7)0.09858 (6)0.0355 (6)
C12A0.1806 (3)0.45333 (8)0.15555 (6)0.0533 (7)
C16A1.3376 (3)0.04489 (9)0.30714 (7)0.0666 (8)
C21A0.7009 (2)0.31252 (7)0.07778 (5)0.0313 (6)
C22A0.5117 (3)0.30645 (7)0.10449 (5)0.0358 (6)
C23A0.3878 (2)0.35387 (7)0.11913 (5)0.0348 (6)
C24A0.4556 (3)0.40885 (7)0.10728 (5)0.0343 (6)
C25A0.6440 (3)0.41628 (8)0.08030 (6)0.0407 (6)
C26A0.7644 (3)0.36880 (7)0.06602 (5)0.0376 (6)
C31A0.5213 (3)0.20584 (8)0.01718 (6)0.0537 (7)
C32A0.7646 (3)0.27174 (8)−0.02963 (6)0.0553 (7)
C61A1.0661 (3)0.14007 (7)0.14514 (6)0.0366 (6)
C62A1.2642 (3)0.14233 (7)0.17425 (6)0.0400 (6)
C63A1.2967 (3)0.11037 (7)0.21842 (6)0.0442 (6)
C64A1.1263 (3)0.07565 (7)0.23337 (6)0.0434 (6)
C65A0.9261 (3)0.07281 (8)0.20450 (7)0.0471 (7)
C66A0.8967 (3)0.10444 (8)0.16116 (6)0.0443 (7)
O2B0.3867 (2)0.50938 (5)0.43235 (4)0.0595 (5)
O4B0.98221 (18)0.30041 (5)0.19962 (4)0.0512 (5)
O6B1.06971 (18)0.05432 (5)0.45240 (4)0.0526 (4)
N1B0.8531 (2)0.28789 (6)0.34345 (5)0.0341 (5)
C2B0.8492 (2)0.34464 (7)0.31903 (5)0.0326 (5)
C3B0.7574 (2)0.33823 (7)0.26337 (5)0.0358 (6)
C4B0.8988 (3)0.29235 (8)0.23961 (6)0.0398 (6)
C5B0.9335 (3)0.23664 (8)0.26753 (6)0.0480 (7)
C6B1.0127 (3)0.24800 (7)0.32211 (6)0.0373 (6)
C12B0.2267 (3)0.49004 (9)0.46597 (7)0.0654 (8)
C16B1.2452 (3)0.05251 (9)0.49107 (6)0.0583 (7)
C21B0.7197 (2)0.38739 (7)0.34875 (5)0.0341 (5)
C22B0.5352 (3)0.37097 (7)0.37446 (6)0.0395 (6)
C23B0.4186 (3)0.40994 (8)0.40256 (6)0.0428 (6)
C24B0.4860 (3)0.46684 (8)0.40507 (6)0.0454 (7)
C25B0.6680 (3)0.48488 (8)0.37891 (6)0.0516 (7)
C26B0.7830 (3)0.44501 (8)0.35184 (6)0.0447 (6)
C31B0.5139 (3)0.31671 (8)0.25968 (6)0.0513 (7)
C32B0.7731 (3)0.39571 (8)0.23597 (6)0.0513 (7)
C61B1.0357 (3)0.19431 (7)0.35393 (6)0.0351 (6)
C62B1.2267 (3)0.18511 (7)0.38464 (6)0.0436 (6)
C63B1.2468 (3)0.13897 (8)0.41753 (6)0.0467 (7)
C64B1.0700 (3)0.10078 (7)0.42025 (6)0.0399 (6)
C65B0.8794 (3)0.10823 (7)0.38913 (6)0.0398 (6)
C66B0.8624 (3)0.15445 (7)0.35672 (6)0.0394 (6)
H1A0.893 (2)0.2402 (7)0.1339 (6)0.051 (5)*
H2A0.995940.276220.059160.0398*
H6A1.174610.197170.093230.0426*
H12A0.114410.491370.161470.0799*
H12B0.063410.426680.142510.0799*
H12C0.249140.438120.187080.0799*
H16A1.324010.019300.336020.0998*
H16B1.464430.032370.288270.0998*
H16C1.362620.084740.318800.0998*
H22A0.464650.268650.113160.0429*
H23A0.257450.348310.137150.0417*
H25A0.690290.454150.071640.0488*
H26A0.893830.374540.047720.0451*
H31A0.518190.179170.045620.0806*
H31B0.416030.237700.021660.0806*
H31C0.477980.18504−0.013850.0806*
H32A0.664120.30445−0.024440.0829*
H32B0.917750.28607−0.032240.0829*
H32C0.715460.25149−0.060570.0829*
H51A0.835320.116880.057580.0539*
H52A1.092800.115090.044390.0539*
H62A1.382030.166320.163990.0480*
H63A1.434810.112610.237890.0530*
H65A0.808290.048790.214770.0565*
H66A0.758440.101980.141760.0532*
H1B0.896 (2)0.2920 (7)0.3749 (6)0.043 (5)*
H2B1.007320.358760.318910.0391*
H6B1.162160.267530.322610.0448*
H12D0.167060.523410.483460.0981*
H12E0.103860.470040.447120.0981*
H12F0.299010.463350.490440.0981*
H16D1.228960.017640.511420.0874*
H16E1.390580.051700.476040.0874*
H16F1.236510.086930.512290.0874*
H22B0.487250.331750.372770.0475*
H23B0.293340.397410.419900.0513*
H25B0.712650.524370.379700.0619*
H26B0.909250.457500.334820.0536*
H31D0.417570.345430.274660.0769*
H31E0.464380.311100.224410.0769*
H31F0.504270.279860.277600.0769*
H32D0.679970.424610.251660.0770*
H32E0.929320.408850.237750.0770*
H32F0.720190.390700.200840.0770*
H51B0.791270.214580.266330.0575*
H52B1.046630.212960.251330.0575*
H62B1.348330.211400.383110.0522*
H63B1.380660.133590.438030.0560*
H65B0.759500.081330.390110.0477*
H66B0.729480.159260.335790.0473*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O2A0.0505 (7)0.0399 (8)0.0464 (7)0.0074 (6)0.0077 (6)−0.0011 (6)
O4A0.0528 (7)0.0718 (10)0.0386 (7)0.0077 (7)0.0099 (6)−0.0160 (6)
O6A0.0631 (8)0.0521 (9)0.0540 (8)0.0058 (7)0.0063 (7)0.0173 (7)
N1A0.0429 (8)0.0325 (9)0.0280 (8)0.0028 (7)0.0057 (7)−0.0020 (7)
C2A0.0319 (9)0.0377 (10)0.0301 (9)−0.0046 (8)0.0042 (7)0.0011 (8)
C3A0.0341 (9)0.0478 (11)0.0274 (9)0.0013 (9)0.0036 (7)−0.0045 (8)
C4A0.0359 (10)0.0518 (12)0.0357 (10)−0.0056 (9)0.0052 (8)−0.0149 (9)
C5A0.0512 (10)0.0410 (11)0.0435 (11)0.0023 (9)0.0108 (8)−0.0082 (9)
C6A0.0366 (9)0.0319 (10)0.0390 (10)0.0018 (8)0.0096 (7)−0.0007 (8)
C12A0.0455 (10)0.0593 (13)0.0559 (12)0.0027 (10)0.0099 (9)−0.0118 (10)
C16A0.0769 (14)0.0720 (16)0.0493 (12)0.0099 (12)−0.0078 (11)0.0159 (11)
C21A0.0308 (9)0.0368 (11)0.0261 (9)0.0018 (8)0.0011 (7)0.0013 (8)
C22A0.0413 (10)0.0337 (10)0.0328 (9)−0.0060 (9)0.0052 (8)−0.0007 (8)
C23A0.0331 (9)0.0406 (11)0.0309 (9)−0.0058 (9)0.0047 (7)−0.0023 (8)
C24A0.0365 (9)0.0348 (11)0.0311 (9)0.0047 (9)−0.0027 (7)−0.0003 (8)
C25A0.0449 (10)0.0357 (11)0.0417 (10)−0.0040 (9)0.0036 (8)0.0112 (9)
C26A0.0365 (9)0.0417 (12)0.0351 (10)−0.0006 (9)0.0073 (7)0.0057 (9)
C31A0.0378 (10)0.0767 (15)0.0470 (11)−0.0055 (10)0.0055 (8)−0.0226 (10)
C32A0.0658 (12)0.0645 (14)0.0359 (11)0.0176 (10)0.0057 (9)0.0023 (10)
C61A0.0388 (10)0.0303 (10)0.0417 (10)0.0020 (9)0.0103 (8)−0.0007 (8)
C62A0.0391 (10)0.0324 (10)0.0494 (11)−0.0008 (9)0.0093 (9)−0.0017 (9)
C63A0.0425 (10)0.0406 (12)0.0490 (11)0.0031 (9)−0.0003 (8)0.0020 (9)
C64A0.0510 (11)0.0357 (11)0.0443 (11)0.0078 (10)0.0098 (9)0.0054 (9)
C65A0.0398 (10)0.0432 (12)0.0596 (12)−0.0008 (9)0.0130 (9)0.0093 (10)
C66A0.0378 (10)0.0432 (12)0.0520 (12)0.0002 (9)0.0032 (8)0.0066 (10)
O2B0.0756 (9)0.0433 (8)0.0625 (9)0.0166 (7)0.0272 (7)0.0037 (7)
O4B0.0599 (8)0.0637 (9)0.0308 (7)−0.0078 (7)0.0104 (6)−0.0002 (6)
O6B0.0638 (8)0.0435 (8)0.0486 (7)0.0014 (7)−0.0118 (6)0.0089 (6)
N1B0.0410 (8)0.0355 (9)0.0258 (8)0.0039 (7)0.0033 (7)0.0037 (7)
C2B0.0335 (9)0.0342 (10)0.0302 (9)−0.0016 (8)0.0032 (7)0.0047 (8)
C3B0.0356 (9)0.0414 (11)0.0308 (9)−0.0024 (8)0.0045 (7)0.0079 (8)
C4B0.0388 (9)0.0510 (12)0.0295 (10)−0.0102 (9)0.0012 (8)−0.0014 (9)
C5B0.0592 (11)0.0495 (13)0.0361 (10)0.0016 (10)0.0106 (8)−0.0046 (9)
C6B0.0345 (9)0.0407 (11)0.0372 (10)−0.0012 (8)0.0066 (8)−0.0001 (9)
C12B0.0748 (13)0.0640 (14)0.0608 (13)0.0176 (12)0.0316 (11)0.0027 (11)
C16B0.0679 (12)0.0560 (13)0.0488 (12)0.0137 (10)−0.0139 (10)0.0079 (10)
C21B0.0351 (9)0.0332 (10)0.0341 (9)−0.0019 (8)0.0042 (7)0.0053 (8)
C22B0.0428 (10)0.0374 (11)0.0390 (10)−0.0033 (9)0.0071 (8)0.0048 (9)
C23B0.0429 (10)0.0467 (12)0.0401 (10)0.0002 (10)0.0129 (8)0.0087 (9)
C24B0.0538 (11)0.0405 (12)0.0431 (11)0.0133 (10)0.0125 (9)0.0072 (9)
C25B0.0663 (12)0.0361 (11)0.0538 (12)−0.0023 (10)0.0157 (10)0.0033 (10)
C26B0.0474 (10)0.0420 (12)0.0463 (11)−0.0023 (10)0.0163 (8)0.0080 (9)
C31B0.0437 (10)0.0721 (14)0.0381 (10)−0.0084 (10)0.0017 (8)0.0035 (9)
C32B0.0655 (12)0.0513 (13)0.0372 (10)0.0009 (10)0.0042 (9)0.0116 (9)
C61B0.0342 (9)0.0343 (10)0.0374 (10)0.0049 (9)0.0064 (8)−0.0009 (8)
C62B0.0350 (10)0.0400 (11)0.0555 (11)−0.0034 (9)0.0016 (9)−0.0010 (10)
C63B0.0400 (10)0.0417 (12)0.0568 (12)0.0061 (10)−0.0089 (9)0.0019 (10)
C64B0.0468 (11)0.0349 (11)0.0376 (10)0.0028 (10)0.0004 (8)−0.0013 (9)
C65B0.0380 (10)0.0391 (11)0.0420 (10)−0.0048 (9)0.0003 (8)−0.0010 (9)
C66B0.0361 (9)0.0440 (12)0.0376 (10)−0.0015 (9)−0.0024 (8)0.0033 (9)

Geometric parameters (Å, °)

O2A—C12A1.429 (2)C31A—H31B0.9800
O2A—C24A1.375 (2)C32A—H32B0.9800
O4A—C4A1.220 (2)C32A—H32C0.9800
O6A—C16A1.417 (2)C32A—H32A0.9800
O6A—C64A1.3699 (19)C62A—H62A0.9500
O2B—C12B1.425 (2)C63A—H63A0.9500
O2B—C24B1.380 (2)C65A—H65A0.9500
O4B—C4B1.223 (2)C66A—H66A0.9500
O6B—C16B1.428 (2)C2B—C3B1.5623 (19)
O6B—C64B1.375 (2)C2B—C21B1.511 (2)
N1A—C2A1.466 (2)C3B—C31B1.535 (2)
N1A—C6A1.468 (2)C3B—C32B1.522 (2)
N1A—H1A0.922 (16)C3B—C4B1.519 (2)
N1B—C6B1.467 (2)C4B—C5B1.495 (3)
N1B—C2B1.464 (2)C5B—C6B1.530 (2)
N1B—H1B0.870 (16)C6B—C61B1.505 (2)
C2A—C3A1.559 (2)C21B—C22B1.388 (2)
C2A—C21A1.506 (2)C21B—C26B1.384 (2)
C3A—C31A1.536 (2)C22B—C23B1.388 (2)
C3A—C32A1.516 (2)C23B—C24B1.374 (3)
C3A—C4A1.519 (2)C24B—C25B1.393 (2)
C4A—C5A1.505 (2)C25B—C26B1.381 (3)
C5A—C6A1.526 (2)C61B—C66B1.391 (2)
C6A—C61A1.505 (2)C61B—C62B1.381 (2)
C21A—C26A1.395 (2)C62B—C63B1.382 (2)
C21A—C22A1.382 (2)C63B—C64B1.382 (3)
C22A—C23A1.392 (2)C64B—C65B1.380 (2)
C23A—C24A1.375 (2)C65B—C66B1.375 (2)
C24A—C25A1.385 (2)C2B—H2B1.0000
C25A—C26A1.378 (2)C5B—H51B0.9900
C61A—C66A1.393 (2)C5B—H52B0.9900
C61A—C62A1.378 (2)C6B—H6B1.0000
C62A—C63A1.397 (2)C12B—H12D0.9800
C63A—C64A1.375 (2)C12B—H12E0.9800
C64A—C65A1.385 (3)C12B—H12F0.9800
C65A—C66A1.373 (3)C16B—H16D0.9800
C2A—H2A1.0000C16B—H16E0.9800
C5A—H51A0.9900C16B—H16F0.9800
C5A—H52A0.9900C22B—H22B0.9500
C6A—H6A1.0000C23B—H23B0.9500
C12A—H12A0.9800C25B—H25B0.9500
C12A—H12C0.9800C26B—H26B0.9500
C12A—H12B0.9800C31B—H31D0.9800
C16A—H16B0.9800C31B—H31E0.9800
C16A—H16A0.9800C31B—H31F0.9800
C16A—H16C0.9800C32B—H32D0.9800
C22A—H22A0.9500C32B—H32E0.9800
C23A—H23A0.9500C32B—H32F0.9800
C25A—H25A0.9500C62B—H62B0.9500
C26A—H26A0.9500C63B—H63B0.9500
C31A—H31C0.9800C65B—H65B0.9500
C31A—H31A0.9800C66B—H66B0.9500
O2A···C16Ai3.291 (2)H12B···C25Axiv2.9300
O4B···N1A3.1958 (17)H12B···C23A2.6700
O6A···C12Aii3.413 (2)H12B···C26Axiv2.9500
O2A···H65Biii2.9100H12B···H23A2.1600
O2A···H16Ai2.6300H12C···C23A2.8200
O2B···H51Aiii2.8300H12C···H23A2.4700
O2B···H12Fiv2.7800H12C···H32Exiv2.5000
O4A···H23Bv2.7300H12D···C5Aiii2.9700
O4A···H1Bvi2.639 (16)H12D···H12Dxi2.4800
O4A···H32C2.5900H12D···H51Aiii2.4200
O4A···H32B2.7300H12D···C12Bxi2.8000
O4B···H32F2.6100H12D···H12Exi2.5400
O4B···H32E2.7300H12E···H23B2.1700
O4B···H1A2.279 (16)H12E···C23B2.6800
O4B···H23Avii2.6600H12E···H12Dxi2.5400
O6A···H12Aii2.6000H12F···O2Biv2.7800
O6B···H25Aviii2.8200H12F···C23B2.7900
O6B···H16Dix2.6600H12F···H23B2.4200
N1A···O4B3.1958 (17)H16A···O2Aviii2.6300
N1A···H22A2.6200H16B···C63A2.7400
N1A···H31A2.6600H16B···H63A2.2900
N1B···H31F2.6500H16C···C62B3.0500
N1B···H22B2.5800H16C···C63A2.7600
N1B···H32Cx2.8900H16C···C63B3.0400
C12A···O6Aiii3.413 (2)H16C···H63A2.3200
C12B···C12Bxi3.389 (3)H16D···O6Bix2.6600
C16A···O2Aviii3.291 (2)H16E···H63B2.1500
C16B···C25Axii3.347 (2)H16E···C63B2.6600
C16B···C24Axii3.401 (2)H16F···H26Ax2.4700
C22A···C31A3.298 (2)H16F···C63B2.8100
C22B···C31B3.312 (2)H16F···H63B2.4600
C24A···C16Bxiii3.401 (2)H16F···C24Axii2.7900
C25A···C16Bxiii3.347 (2)H16F···C25Axii2.9500
C26A···C32A3.402 (2)H22A···N1A2.6200
C26B···C32B3.300 (2)H22A···C31A2.9900
C31A···C22A3.298 (2)H22A···H6Axiv2.4300
C31B···C22B3.312 (2)H22A···H31B2.5500
C32A···C26A3.402 (2)H22B···C31B3.0600
C32A···C66Bvi3.566 (2)H22B···N1B2.5800
C32B···C26B3.300 (2)H23A···C12A2.5200
C66B···C32Ax3.566 (2)H23A···O4Bxiv2.6600
C4B···H1A3.073 (16)H23A···H12B2.1600
C5A···H31A2.8200H23A···H12C2.4700
C5A···H12Dii2.9700H23B···C12B2.5100
C5A···H66A2.9300H23B···O4Axv2.7300
C5B···H31F2.7800H23B···H12E2.1700
C5B···H66B2.8800H23B···H12F2.4200
C12A···H23A2.5200H25A···O6Bi2.8200
C12A···H32Exiv2.9300H25A···C16Bi2.8600
C12B···H12Dxi2.8000H25B···C61Ai3.0700
C12B···H51Aiii3.0100H25B···C62Ai3.0900
C12B···H23B2.5100H26A···H16Fvi2.4700
C16A···H63A2.5200H26A···H2A2.3700
C16B···H63B2.5100H26B···C65Ai3.0500
C16B···H25Aviii2.8600H26B···C32B3.0700
C21A···H32A2.7400H26B···H2B2.4000
C21A···H31B2.8000H31A···C5A2.8200
C21B···H32D2.7300H31A···H6Axiv2.5200
C21B···H31D2.7700H31A···H51A2.3900
C22A···H1A2.816 (14)H31A···N1A2.6600
C22A···H31B2.7600H31B···H22A2.5500
C22B···H1B2.823 (14)H31B···H32A2.5100
C22B···H31D2.7800H31B···C21A2.8000
C23A···H32F2.9900H31B···C22A2.7600
C23A···H12C2.8200H31C···H32C2.4800
C23A···H31E2.9900H31D···C21B2.7700
C23A···H12B2.6700H31D···H32D2.5100
C23B···H12F2.7900H31D···C22B2.7800
C23B···H12E2.6800H31E···H32F2.5000
C24A···H16Fxiii2.7900H31E···C23A2.9900
C24A···H32F2.9100H31F···H51B2.3200
C25A···H16Fxiii2.9500H31F···N1B2.6500
C25A···H12Bvii2.9300H31F···C5B2.7800
C26A···H12Bvii2.9500H31F···H6Bxiv2.4500
C26A···H32A2.8700H32A···C26A2.8700
C26B···H32D2.7500H32A···H31B2.5100
C31A···H51A2.9400H32A···H63Bxiii2.3900
C31A···H6Axiv3.0000H32A···C21A2.7400
C31A···H22A2.9900H32B···C64Bvi3.0700
C31B···H22B3.0600H32B···H2A2.4700
C31B···H51B2.8800H32B···C62Bvi3.0500
C31B···H6Bxiv3.0000H32B···O4A2.7300
C32A···H1Bvi3.092 (16)H32B···C63Bvi3.0000
C32B···H26B3.0700H32C···O4A2.5900
C61A···H25Bviii3.0700H32C···H31C2.4800
C62A···H52B2.9900H32C···N1Bvi2.8900
C62A···H25Bviii3.0900H32C···H1Bvi2.3200
C62B···H16C3.0500H32D···C21B2.7300
C62B···H32Bx3.0500H32D···C26B2.7500
C63A···H52B2.9600H32D···H31D2.5100
C63A···H16B2.7400H32E···O4B2.7300
C63A···H16C2.7600H32E···H12Cvii2.5000
C63B···H16F2.8100H32E···C12Avii2.9300
C63B···H16C3.0400H32E···H2B2.4800
C63B···H16E2.6600H32F···O4B2.6100
C63B···H32Bx3.0000H32F···H31E2.5000
C64B···H32Bx3.0700H32F···C23A2.9900
C65A···H26Bviii3.0500H32F···C24A2.9100
C65B···H12Aii3.0200H51A···C31A2.9400
C66A···H51A2.7900H51A···C66A2.7900
C66B···H51B2.8000H51A···H31A2.3900
H1A···O4B2.279 (16)H51A···H66A2.3500
H1A···C4B3.073 (16)H51A···O2Bii2.8300
H1A···C22A2.816 (14)H51A···C12Bii3.0100
H1B···C22B2.823 (14)H51A···H12Dii2.4200
H1B···H32Cx2.3200H51B···C66B2.8000
H1B···O4Ax2.639 (16)H51B···H31F2.3200
H1B···C32Ax3.092 (16)H51B···H66B2.3000
H2A···H6A2.2800H51B···C31B2.8800
H2A···H26A2.3700H52B···C63A2.9600
H2A···H32B2.4700H52B···C62A2.9900
H2B···H6B2.3000H62A···H6A2.3100
H2B···H32E2.4800H62B···H6B2.3100
H2B···H26B2.4000H63A···C16A2.5200
H6A···H2A2.2800H63A···H16B2.2900
H6A···C31Avii3.0000H63A···H16C2.3200
H6A···H62A2.3100H63B···H16E2.1500
H6A···H22Avii2.4300H63B···H16F2.4600
H6A···H31Avii2.5200H63B···C16B2.5100
H6B···C31Bvii3.0000H63B···H32Axii2.3900
H6B···H2B2.3000H65B···O2Aii2.9100
H6B···H31Fvii2.4500H66A···H51A2.3500
H6B···H62B2.3100H66A···C5A2.9300
H12A···O6Aiii2.6000H66B···C5B2.8800
H12A···C65Biii3.0200H66B···H51B2.3000
C12A—O2A—C24A116.51 (13)C62A—C63A—H63A120.00
C16A—O6A—C64A117.66 (13)C64A—C65A—H65A120.00
C12B—O2B—C24B116.02 (14)C66A—C65A—H65A120.00
C16B—O6B—C64B116.55 (13)C61A—C66A—H66A119.00
C2A—N1A—C6A111.88 (12)C65A—C66A—H66A119.00
C6A—N1A—H1A108.2 (8)N1B—C2B—C21B110.14 (11)
C2A—N1A—H1A107.3 (10)N1B—C2B—C3B109.63 (12)
C2B—N1B—C6B112.39 (12)C3B—C2B—C21B113.75 (11)
C6B—N1B—H1B106.6 (9)C2B—C3B—C31B111.57 (11)
C2B—N1B—H1B109.3 (11)C2B—C3B—C4B107.07 (11)
N1A—C2A—C3A109.70 (13)C4B—C3B—C32B110.73 (12)
N1A—C2A—C21A109.51 (11)C31B—C3B—C32B109.73 (12)
C3A—C2A—C21A115.09 (11)C4B—C3B—C31B107.29 (13)
C4A—C3A—C32A110.15 (12)C2B—C3B—C32B110.39 (13)
C31A—C3A—C32A109.70 (12)O4B—C4B—C5B121.12 (16)
C4A—C3A—C31A107.09 (14)O4B—C4B—C3B121.87 (15)
C2A—C3A—C31A111.69 (11)C3B—C4B—C5B117.01 (14)
C2A—C3A—C32A110.14 (13)C4B—C5B—C6B110.78 (14)
C2A—C3A—C4A108.01 (11)N1B—C6B—C5B108.00 (14)
O4A—C4A—C3A122.08 (15)C5B—C6B—C61B114.27 (14)
O4A—C4A—C5A121.25 (16)N1B—C6B—C61B109.61 (13)
C3A—C4A—C5A116.67 (13)C2B—C21B—C26B120.82 (13)
C4A—C5A—C6A112.21 (14)C2B—C21B—C22B122.09 (14)
C5A—C6A—C61A113.75 (13)C22B—C21B—C26B117.09 (14)
N1A—C6A—C61A110.25 (13)C21B—C22B—C23B122.18 (15)
N1A—C6A—C5A108.34 (14)C22B—C23B—C24B119.38 (16)
C2A—C21A—C26A120.51 (12)C23B—C24B—C25B119.79 (16)
C22A—C21A—C26A117.00 (14)O2B—C24B—C25B115.34 (16)
C2A—C21A—C22A122.43 (14)O2B—C24B—C23B124.88 (16)
C21A—C22A—C23A122.19 (15)C24B—C25B—C26B119.60 (17)
C22A—C23A—C24A119.45 (13)C21B—C26B—C25B121.94 (16)
O2A—C24A—C25A115.61 (14)C62B—C61B—C66B117.21 (15)
C23A—C24A—C25A119.67 (15)C6B—C61B—C62B120.43 (15)
O2A—C24A—C23A124.72 (14)C6B—C61B—C66B122.20 (15)
C24A—C25A—C26A120.08 (16)C61B—C62B—C63B122.24 (16)
C21A—C26A—C25A121.61 (15)C62B—C63B—C64B119.25 (16)
C62A—C61A—C66A117.66 (15)O6B—C64B—C65B116.23 (15)
C6A—C61A—C66A121.18 (15)O6B—C64B—C63B124.14 (15)
C6A—C61A—C62A121.13 (15)C63B—C64B—C65B119.63 (15)
C61A—C62A—C63A121.89 (16)C64B—C65B—C66B120.24 (16)
C62A—C63A—C64A119.17 (16)C61B—C66B—C65B121.40 (16)
C63A—C64A—C65A119.69 (15)N1B—C2B—H2B108.00
O6A—C64A—C65A115.67 (15)C3B—C2B—H2B108.00
O6A—C64A—C63A124.65 (15)C21B—C2B—H2B108.00
C64A—C65A—C66A120.48 (17)C4B—C5B—H51B110.00
C61A—C66A—C65A121.12 (16)C4B—C5B—H52B109.00
C3A—C2A—H2A107.00C6B—C5B—H51B109.00
C21A—C2A—H2A107.00C6B—C5B—H52B109.00
N1A—C2A—H2A107.00H51B—C5B—H52B108.00
H51A—C5A—H52A108.00N1B—C6B—H6B108.00
C4A—C5A—H51A109.00C5B—C6B—H6B108.00
C4A—C5A—H52A109.00C61B—C6B—H6B108.00
C6A—C5A—H52A109.00O2B—C12B—H12D109.00
C6A—C5A—H51A109.00O2B—C12B—H12E109.00
C5A—C6A—H6A108.00O2B—C12B—H12F109.00
C61A—C6A—H6A108.00H12D—C12B—H12E109.00
N1A—C6A—H6A108.00H12D—C12B—H12F109.00
H12B—C12A—H12C109.00H12E—C12B—H12F109.00
O2A—C12A—H12A109.00O6B—C16B—H16D109.00
H12A—C12A—H12B109.00O6B—C16B—H16E109.00
H12A—C12A—H12C109.00O6B—C16B—H16F109.00
O2A—C12A—H12B109.00H16D—C16B—H16E109.00
O2A—C12A—H12C109.00H16D—C16B—H16F109.00
O6A—C16A—H16A109.00H16E—C16B—H16F109.00
H16B—C16A—H16C109.00C21B—C22B—H22B119.00
O6A—C16A—H16B109.00C23B—C22B—H22B119.00
O6A—C16A—H16C109.00C22B—C23B—H23B120.00
H16A—C16A—H16B109.00C24B—C23B—H23B120.00
H16A—C16A—H16C109.00C24B—C25B—H25B120.00
C21A—C22A—H22A119.00C26B—C25B—H25B120.00
C23A—C22A—H22A119.00C21B—C26B—H26B119.00
C24A—C23A—H23A120.00C25B—C26B—H26B119.00
C22A—C23A—H23A120.00C3B—C31B—H31D109.00
C26A—C25A—H25A120.00C3B—C31B—H31E109.00
C24A—C25A—H25A120.00C3B—C31B—H31F109.00
C21A—C26A—H26A119.00H31D—C31B—H31E109.00
C25A—C26A—H26A119.00H31D—C31B—H31F109.00
C3A—C31A—H31C109.00H31E—C31B—H31F109.00
H31A—C31A—H31B109.00C3B—C32B—H32D109.00
C3A—C31A—H31B109.00C3B—C32B—H32E109.00
C3A—C31A—H31A109.00C3B—C32B—H32F109.00
H31A—C31A—H31C109.00H32D—C32B—H32E109.00
H31B—C31A—H31C109.00H32D—C32B—H32F109.00
H32A—C32A—H32B109.00H32E—C32B—H32F109.00
C3A—C32A—H32B109.00C61B—C62B—H62B119.00
H32A—C32A—H32C109.00C63B—C62B—H62B119.00
C3A—C32A—H32C109.00C62B—C63B—H63B120.00
C3A—C32A—H32A109.00C64B—C63B—H63B120.00
H32B—C32A—H32C109.00C64B—C65B—H65B120.00
C63A—C62A—H62A119.00C66B—C65B—H65B120.00
C61A—C62A—H62A119.00C61B—C66B—H66B119.00
C64A—C63A—H63A120.00C65B—C66B—H66B119.00
C12A—O2A—C24A—C23A12.1 (2)C62A—C61A—C66A—C65A0.2 (3)
C12A—O2A—C24A—C25A−168.43 (13)C66A—C61A—C62A—C63A−0.1 (3)
C16A—O6A—C64A—C63A1.5 (2)C61A—C62A—C63A—C64A0.0 (3)
C16A—O6A—C64A—C65A−178.59 (15)C62A—C63A—C64A—C65A0.1 (3)
C12B—O2B—C24B—C25B−169.55 (15)C62A—C63A—C64A—O6A−179.98 (14)
C12B—O2B—C24B—C23B10.2 (2)C63A—C64A—C65A—C66A−0.1 (3)
C16B—O6B—C64B—C63B12.0 (2)O6A—C64A—C65A—C66A−180.00 (17)
C16B—O6B—C64B—C65B−168.29 (14)C64A—C65A—C66A—C61A−0.1 (3)
C6A—N1A—C2A—C3A66.28 (14)C21B—C2B—C3B—C31B−60.64 (17)
C2A—N1A—C6A—C5A−63.66 (16)N1B—C2B—C3B—C32B−174.56 (11)
C2A—N1A—C6A—C61A171.27 (13)C21B—C2B—C3B—C4B−177.75 (13)
C6A—N1A—C2A—C21A−166.52 (12)N1B—C2B—C21B—C26B145.00 (14)
C2B—N1B—C6B—C5B−63.96 (16)C3B—C2B—C21B—C22B89.25 (17)
C6B—N1B—C2B—C21B−168.54 (12)C3B—C2B—C21B—C26B−91.48 (16)
C2B—N1B—C6B—C61B170.98 (12)N1B—C2B—C3B—C31B63.15 (15)
C6B—N1B—C2B—C3B65.58 (14)C21B—C2B—C3B—C32B61.65 (15)
C3A—C2A—C21A—C22A85.52 (16)N1B—C2B—C21B—C22B−34.27 (17)
C3A—C2A—C21A—C26A−97.35 (15)N1B—C2B—C3B—C4B−53.96 (14)
N1A—C2A—C21A—C26A138.54 (13)C2B—C3B—C4B—C5B49.08 (18)
N1A—C2A—C21A—C22A−38.59 (17)C32B—C3B—C4B—O4B−10.1 (2)
N1A—C2A—C3A—C4A−54.13 (14)C32B—C3B—C4B—C5B169.46 (14)
C21A—C2A—C3A—C32A61.54 (15)C2B—C3B—C4B—O4B−130.49 (16)
N1A—C2A—C3A—C31A63.39 (15)C31B—C3B—C4B—O4B109.62 (18)
C21A—C2A—C3A—C31A−60.62 (17)C31B—C3B—C4B—C5B−70.82 (17)
C21A—C2A—C3A—C4A−178.14 (12)C3B—C4B—C5B—C6B−50.2 (2)
N1A—C2A—C3A—C32A−174.46 (11)O4B—C4B—C5B—C6B129.34 (17)
C32A—C3A—C4A—C5A166.77 (14)C4B—C5B—C6B—C61B175.78 (15)
C2A—C3A—C4A—O4A−133.38 (16)C4B—C5B—C6B—N1B53.53 (18)
C32A—C3A—C4A—O4A−13.1 (2)N1B—C6B—C61B—C62B−106.34 (18)
C2A—C3A—C4A—C5A46.45 (18)C5B—C6B—C61B—C66B−52.6 (2)
C31A—C3A—C4A—C5A−73.99 (17)C5B—C6B—C61B—C62B132.31 (17)
C31A—C3A—C4A—O4A106.18 (18)N1B—C6B—C61B—C66B68.76 (19)
O4A—C4A—C5A—C6A133.11 (17)C22B—C21B—C26B—C25B−0.4 (2)
C3A—C4A—C5A—C6A−46.7 (2)C2B—C21B—C26B—C25B−179.75 (14)
C4A—C5A—C6A—C61A174.80 (15)C2B—C21B—C22B—C23B178.75 (14)
C4A—C5A—C6A—N1A51.82 (18)C26B—C21B—C22B—C23B−0.6 (2)
C5A—C6A—C61A—C66A−57.7 (2)C21B—C22B—C23B—C24B0.3 (3)
N1A—C6A—C61A—C62A−113.79 (17)C22B—C23B—C24B—C25B0.9 (3)
N1A—C6A—C61A—C66A64.2 (2)C22B—C23B—C24B—O2B−178.81 (15)
C5A—C6A—C61A—C62A124.29 (17)O2B—C24B—C25B—C26B177.89 (15)
C26A—C21A—C22A—C23A0.2 (2)C23B—C24B—C25B—C26B−1.9 (3)
C2A—C21A—C22A—C23A177.45 (13)C24B—C25B—C26B—C21B1.6 (3)
C2A—C21A—C26A—C25A−177.36 (14)C6B—C61B—C66B—C65B−174.47 (15)
C22A—C21A—C26A—C25A−0.1 (2)C62B—C61B—C66B—C65B0.8 (2)
C21A—C22A—C23A—C24A−0.7 (2)C6B—C61B—C62B—C63B174.43 (16)
C22A—C23A—C24A—C25A1.0 (2)C66B—C61B—C62B—C63B−0.9 (2)
C22A—C23A—C24A—O2A−179.58 (13)C61B—C62B—C63B—C64B−0.5 (3)
C23A—C24A—C25A—C26A−0.9 (2)C62B—C63B—C64B—C65B2.0 (3)
O2A—C24A—C25A—C26A179.66 (14)C62B—C63B—C64B—O6B−178.38 (15)
C24A—C25A—C26A—C21A0.4 (2)O6B—C64B—C65B—C66B178.22 (15)
C6A—C61A—C66A—C65A−177.91 (16)C63B—C64B—C65B—C66B−2.1 (3)
C6A—C61A—C62A—C63A177.96 (15)C64B—C65B—C66B—C61B0.7 (3)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1A—H1A···O4B0.92 (2)2.28 (2)3.1958 (17)173.2 (14)
C25B—H25B···Cg1i0.952.953.6993 (19)137
C32A—H32B···Cg2vi0.982.823.4573 (19)124
C5B—H52B···Cg10.992.973.7989 (19)142

Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (vi) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2288).

References

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