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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o456.
Published online 2009 February 4. doi:  10.1107/S1600536809001305
PMCID: PMC2968627

2-Cyclo­hexyl-4-[(3,5-dimethyl­piperidin-1-yl)meth­yl]-5-methyl­phenol

Abstract

The title compound, C21H33NO, crystallizes with three independent mol­ecules in the asymmetric unit. The cyclo­hexane and piperidine rings adopt chair conformations. The crystal packing is stabilized by inter­molecular O—H(...)N and C—H(...)O hydrogen bonds, and by weak π–π stacking inter­actions [centroid–centroid distance = 3.876 (2) Å].

Related literature

For the biological activity of amidomethylphenol derivatives, see: Zhang et al. (1986 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-0o456-scheme1.jpg

Experimental

Crystal data

  • C21H33NO
  • M r = 315.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o456-efi1.jpg
  • a = 12.0551 (7) Å
  • b = 16.5513 (10) Å
  • c = 16.7371 (10) Å
  • α = 78.969 (1)°
  • β = 69.354 (1)°
  • γ = 71.951 (1)°
  • V = 2958.6 (3) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.06 mm−1
  • T = 273 (2) K
  • 0.18 × 0.15 × 0.12 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 15478 measured reflections
  • 10326 independent reflections
  • 6658 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.219
  • S = 1.03
  • 10326 reflections
  • 634 parameters
  • 1296 restraints
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.60 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001305/hg2466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001305/hg2466Isup2.hkl

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

supplementary crystallographic information

Comment

4-amidomethyl-phenol derivatives have anti-inflammatory active [Zhang et al., 1986]. The title compound is a derivative of it. In this paper, we report the crystal structure of the title compound.

The title compound, C21H33NO, crystallizes with three independent molecules in the asymmetric unit; all bond lengths are normal (Allen et al., 1987). The cyclohexane (C7—C12; C28—C33; C49—C54) and piperidine ring (N1/C15—C19; N2/C36—C40; N3/C57—C61) adopt chair conformations. The relatively short distance of 3.876 (2)Å between the centroids of benzene ring C43—C48 [at (–X,-Y,1-Z)] indicates the presence of weak π-π interactions, which contribute to the stability of the crystal packing. The crystal packing is also stabilized by intermolecular O—H···N and C—H···O hydrogen bonds,

Experimental

The title compound was prepared by reaction of 2-cyclohexyl-5-methylphenol (1.90 g, 0.01 mol) with 3,5-dimethylpiperidine(1.13 g, 0.01 mol) and 36% formaldehyde solution(1.00 g, 0.012 mol) in 10 mL of 95% alcohol under reflux for 3 h. After removing of the solvent, the residue was recrystallized from ethanol to afford 2.74 g of the title compound with yield of 87%. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution at room temperature for two weeks.

Refinement

All C atoms closer than 3.8Å are restrained with effective standard deviation 0.01Å to have the same Uij components. All H atoms were placed in calculated positions, with C—H = 0.93–0.98Å, O—H = 0.82Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 (1.5 for methyl and phenol)times Ueq(C, O).

Figures

Fig. 1.
View of the title compound (I), with displacement ellipsoids drawn at the 35% probability level.

Crystal data

C21H33NOZ = 6
Mr = 315.48F(000) = 1044
Triclinic, P1Dx = 1.062 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.0551 (7) ÅCell parameters from 4912 reflections
b = 16.5513 (10) Åθ = 2.6–24.6°
c = 16.7371 (10) ŵ = 0.06 mm1
α = 78.969 (1)°T = 273 K
β = 69.354 (1)°Block, colourless
γ = 71.951 (1)°0.18 × 0.15 × 0.12 mm
V = 2958.6 (3) Å3

Data collection

Bruker SMART CCD area-detector diffractometer6658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 25.1°, θmin = 1.3°
[var phi] and ω scansh = −13→14
15478 measured reflectionsk = −19→19
10326 independent reflectionsl = −19→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.1179P)2 + 0.8741P] where P = (Fo2 + 2Fc2)/3
10326 reflections(Δ/σ)max = 0.003
634 parametersΔρmax = 0.67 e Å3
1296 restraintsΔρmin = −0.60 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
O11.10328 (19)0.64137 (14)0.37255 (14)0.0619 (5)
H11.15840.61150.39150.093*
O20.6324 (2)0.59539 (14)0.06614 (15)0.0715 (6)
H20.60970.62630.02720.107*
O3−0.21541 (19)−0.00005 (13)0.43573 (14)0.0584 (5)
H3−0.2175−0.03550.47750.088*
N10.6856 (2)0.46313 (14)0.58429 (14)0.0487 (5)
N20.4452 (2)0.28225 (16)0.06114 (17)0.0611 (7)
N30.2293 (2)0.13009 (14)0.42672 (15)0.0494 (6)
C10.9930 (3)0.62786 (17)0.42522 (19)0.0510 (7)
C20.8988 (3)0.64123 (17)0.38983 (18)0.0519 (7)
C30.7938 (3)0.61861 (17)0.44360 (19)0.0532 (7)
H3A0.73120.62460.42100.064*
C40.7757 (3)0.58758 (17)0.52915 (18)0.0501 (6)
C50.8661 (3)0.58369 (16)0.56485 (18)0.0495 (6)
C60.9730 (3)0.60285 (16)0.51190 (18)0.0503 (6)
H61.03440.59890.53510.060*
C70.9133 (3)0.6773 (2)0.2981 (2)0.0706 (8)
H70.99910.65320.26520.085*
C80.8928 (6)0.7691 (3)0.2858 (3)0.1133 (13)
H8A0.94910.78430.30600.136*
H8B0.80980.79530.32010.136*
C90.9104 (7)0.8048 (4)0.1929 (4)0.1432 (17)
H9A0.88290.86650.19100.172*
H9B0.99770.78960.16180.172*
C100.8498 (6)0.7776 (4)0.1498 (3)0.1223 (15)
H10A0.88170.79360.08890.147*
H10B0.76310.80720.16880.147*
C110.8626 (6)0.6886 (4)0.1629 (3)0.1261 (15)
H11A0.94540.65940.13090.151*
H11B0.80600.67580.14090.151*
C120.8373 (5)0.6555 (3)0.2571 (3)0.1059 (12)
H12A0.75120.67900.28760.127*
H12B0.85260.59390.26220.127*
C130.8491 (3)0.5612 (2)0.65912 (19)0.0664 (8)
H13A0.92230.56030.67040.100*
H13B0.83350.50590.67590.100*
H13C0.78080.60290.69120.100*
C140.6631 (3)0.55707 (18)0.5806 (2)0.0574 (7)
H14A0.63540.57350.63860.069*
H14B0.59800.58510.55550.069*
C150.6948 (3)0.43837 (18)0.50216 (18)0.0519 (7)
H15A0.76000.45810.45700.062*
H15B0.61850.46620.48950.062*
C160.7207 (3)0.34242 (18)0.50235 (18)0.0534 (7)
H160.79940.31550.51330.064*
C170.6217 (3)0.3107 (2)0.5750 (2)0.0617 (8)
H17A0.54480.33140.56200.074*
H17B0.64380.24880.57940.074*
C180.6036 (3)0.3397 (2)0.66034 (19)0.0605 (7)
H180.67820.31180.67640.073*
C190.5851 (3)0.4355 (2)0.65256 (19)0.0577 (7)
H19A0.50830.46410.64090.069*
H19B0.57920.45220.70670.069*
C200.7321 (3)0.3187 (2)0.4159 (2)0.0706 (9)
H20A0.74730.25800.41810.106*
H20B0.79900.33670.37240.106*
H20C0.65710.34640.40270.106*
C210.4957 (4)0.3140 (3)0.7307 (3)0.0894 (11)
H21A0.42140.34110.71640.134*
H21B0.48820.33160.78420.134*
H21C0.50970.25320.73570.134*
C220.5783 (3)0.5293 (2)0.09074 (18)0.0602 (7)
C230.6489 (3)0.4483 (2)0.11016 (19)0.0619 (8)
C240.5923 (3)0.3825 (2)0.1302 (2)0.0663 (8)
H240.63680.32810.14460.080*
C250.4732 (3)0.3923 (2)0.13011 (19)0.0630 (8)
C260.4017 (3)0.4754 (2)0.11550 (18)0.0620 (8)
C270.4568 (3)0.5415 (2)0.09701 (18)0.0622 (8)
H270.41000.59680.08840.075*
C280.7785 (3)0.4360 (2)0.1079 (2)0.0700 (8)
H280.80960.48050.06620.084*
C290.7838 (4)0.4489 (3)0.1931 (3)0.0876 (10)
H29A0.74680.40890.23690.105*
H29B0.73560.50610.20770.105*
C300.9135 (4)0.4367 (3)0.1936 (3)0.1053 (12)
H30A0.94470.48340.15800.126*
H30B0.91120.43910.25160.126*
C310.9995 (4)0.3547 (3)0.1620 (3)0.1037 (12)
H31A1.08230.35370.15750.124*
H31B0.97710.30770.20290.124*
C320.9964 (4)0.3432 (3)0.0769 (3)0.1060 (13)
H32A1.04880.28760.05990.127*
H32B1.02840.38610.03450.127*
C330.8665 (4)0.3505 (3)0.0791 (3)0.0946 (11)
H33A0.83710.30460.11800.113*
H33B0.86750.34420.02240.113*
C340.2702 (3)0.4943 (2)0.1181 (2)0.0763 (10)
H34A0.23770.55480.10860.114*
H34B0.22280.47370.17320.114*
H34C0.26640.46640.07430.114*
C350.4258 (4)0.3152 (2)0.1425 (2)0.0731 (9)
H35A0.46650.27030.17730.088*
H35B0.33860.32990.17380.088*
C360.5750 (3)0.2413 (2)0.0207 (2)0.0756 (9)
H36A0.60340.19410.05920.091*
H36B0.62280.28200.01040.091*
C370.5955 (4)0.2089 (3)−0.0631 (3)0.0869 (11)
H370.56650.2577−0.10090.104*
C380.5210 (4)0.1466 (3)−0.0487 (3)0.0957 (12)
H38A0.55330.0954−0.01580.115*
H38B0.52900.1305−0.10370.115*
C390.3860 (4)0.1833 (2)−0.0015 (3)0.0838 (10)
H390.35300.2305−0.03920.101*
C400.3732 (4)0.2195 (2)0.0780 (3)0.0780 (9)
H40A0.28720.24680.10500.094*
H40B0.39980.17310.11800.094*
C410.7318 (5)0.1706 (4)−0.1068 (4)0.147 (2)
H41A0.76370.1247−0.06960.221*
H41B0.77500.2138−0.11920.221*
H41C0.74250.1493−0.15930.221*
C420.3106 (5)0.1188 (3)0.0200 (4)0.1225 (17)
H42A0.33240.07640.06360.184*
H42B0.32720.0919−0.03050.184*
H42C0.22480.14750.04030.184*
C43−0.1430 (2)0.05018 (16)0.43318 (19)0.0480 (6)
C44−0.0715 (3)0.07848 (16)0.35358 (18)0.0480 (6)
C450.0061 (3)0.12507 (16)0.35401 (19)0.0499 (6)
H450.05430.14500.30150.060*
C460.0160 (3)0.14376 (16)0.42838 (19)0.0496 (6)
C47−0.0631 (3)0.11979 (16)0.50753 (19)0.0507 (7)
C48−0.1412 (3)0.07321 (17)0.50803 (19)0.0506 (6)
H48−0.19400.05690.56020.061*
C49−0.0817 (3)0.05966 (18)0.27171 (19)0.0533 (7)
H49−0.09950.00390.28270.064*
C500.0341 (3)0.0550 (3)0.1946 (2)0.0772 (9)
H50A0.10200.01140.20800.093*
H50B0.05480.10920.18250.093*
C510.0166 (4)0.0342 (3)0.1154 (2)0.0842 (10)
H51A0.09010.03460.06680.101*
H51B0.0044−0.02260.12550.101*
C52−0.0920 (4)0.0976 (3)0.0949 (2)0.0906 (11)
H52A−0.07490.15300.07730.109*
H52B−0.10490.08000.04760.109*
C53−0.2063 (4)0.1049 (3)0.1706 (3)0.0969 (12)
H53A−0.22970.05170.18320.116*
H53B−0.27260.14960.15650.116*
C54−0.1892 (3)0.1251 (2)0.2497 (2)0.0748 (9)
H54A−0.17510.18130.23950.090*
H54B−0.26360.12590.29790.090*
C55−0.0657 (3)0.14181 (19)0.5918 (2)0.0628 (8)
H55A−0.12090.11550.63820.094*
H55B−0.09320.20260.59380.094*
H55C0.01540.12130.59710.094*
C560.1100 (3)0.18862 (17)0.4224 (2)0.0565 (7)
H56A0.12390.22480.36890.068*
H56B0.07720.22520.46880.068*
C570.2979 (3)0.08899 (19)0.3469 (2)0.0596 (7)
H57A0.31130.13260.29940.072*
H57B0.24920.05720.33700.072*
C580.4213 (3)0.0288 (2)0.3492 (2)0.0686 (8)
H580.4057−0.01580.39630.082*
C590.4963 (3)0.0770 (2)0.3680 (2)0.0721 (9)
H59A0.57120.03710.37510.087*
H59B0.51930.11790.31950.087*
C600.4267 (3)0.1235 (2)0.4478 (2)0.0648 (8)
H600.41210.08070.49690.078*
C610.3019 (3)0.17908 (19)0.4420 (2)0.0588 (7)
H61A0.25610.20580.49500.071*
H61B0.31440.22400.39580.071*
C620.4879 (4)−0.0142 (3)0.2659 (3)0.1078 (14)
H62A0.50480.02830.21870.162*
H62B0.4370−0.04410.25710.162*
H62C0.5637−0.05390.26940.162*
C630.4964 (4)0.1775 (3)0.4643 (3)0.0931 (12)
H63A0.57500.14220.46750.140*
H63B0.45030.20240.51750.140*
H63C0.50790.22190.41850.140*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0532 (12)0.0626 (13)0.0691 (14)−0.0152 (10)−0.0237 (11)0.0043 (10)
O20.0892 (17)0.0569 (13)0.0712 (15)−0.0115 (12)−0.0379 (13)−0.0005 (11)
O30.0615 (13)0.0554 (12)0.0710 (14)−0.0242 (10)−0.0341 (11)0.0048 (10)
N10.0448 (13)0.0522 (13)0.0446 (13)−0.0079 (10)−0.0132 (10)−0.0036 (10)
N20.0621 (16)0.0525 (14)0.0649 (16)−0.0071 (12)−0.0263 (13)0.0020 (12)
N30.0512 (13)0.0420 (12)0.0612 (15)−0.0105 (10)−0.0254 (12)−0.0068 (10)
C10.0568 (16)0.0406 (13)0.0564 (16)−0.0098 (12)−0.0206 (13)−0.0061 (11)
C20.0574 (16)0.0460 (14)0.0536 (15)−0.0100 (12)−0.0228 (13)−0.0031 (12)
C30.0551 (15)0.0501 (14)0.0571 (16)−0.0066 (12)−0.0272 (13)−0.0051 (12)
C40.0505 (15)0.0404 (13)0.0536 (15)−0.0025 (11)−0.0146 (12)−0.0100 (11)
C50.0571 (16)0.0386 (13)0.0494 (15)−0.0014 (12)−0.0194 (13)−0.0095 (11)
C60.0562 (16)0.0416 (13)0.0575 (16)−0.0043 (12)−0.0280 (13)−0.0093 (12)
C70.077 (2)0.0777 (19)0.0601 (17)−0.0229 (16)−0.0304 (15)0.0085 (15)
C80.173 (3)0.089 (2)0.092 (2)−0.048 (2)−0.061 (2)0.016 (2)
C90.208 (4)0.119 (3)0.112 (3)−0.064 (3)−0.067 (3)0.035 (3)
C100.148 (3)0.135 (3)0.085 (3)−0.034 (3)−0.063 (3)0.032 (3)
C110.178 (4)0.137 (3)0.077 (2)−0.049 (3)−0.057 (3)0.004 (2)
C120.146 (3)0.108 (2)0.078 (2)−0.045 (2)−0.049 (2)0.0006 (19)
C130.081 (2)0.0647 (19)0.0506 (17)−0.0082 (16)−0.0224 (16)−0.0126 (14)
C140.0505 (16)0.0531 (15)0.0585 (16)−0.0005 (12)−0.0147 (13)−0.0091 (13)
C150.0454 (14)0.0581 (15)0.0487 (15)−0.0057 (12)−0.0197 (12)−0.0005 (12)
C160.0506 (16)0.0551 (16)0.0542 (16)−0.0066 (13)−0.0226 (13)−0.0045 (12)
C170.0588 (17)0.0635 (17)0.0653 (18)−0.0193 (14)−0.0229 (15)−0.0001 (14)
C180.0585 (17)0.0688 (18)0.0538 (17)−0.0207 (14)−0.0192 (14)0.0047 (14)
C190.0490 (16)0.0680 (17)0.0502 (16)−0.0107 (13)−0.0136 (13)−0.0037 (13)
C200.074 (2)0.076 (2)0.063 (2)−0.0099 (17)−0.0256 (17)−0.0169 (16)
C210.092 (3)0.097 (3)0.074 (2)−0.040 (2)−0.013 (2)0.005 (2)
C220.0768 (19)0.0560 (16)0.0434 (15)−0.0065 (14)−0.0221 (14)−0.0067 (12)
C230.0769 (19)0.0579 (16)0.0490 (15)−0.0081 (15)−0.0262 (14)−0.0046 (13)
C240.081 (2)0.0585 (16)0.0548 (16)−0.0058 (15)−0.0313 (15)0.0031 (13)
C250.0766 (19)0.0645 (17)0.0440 (15)−0.0138 (15)−0.0224 (14)0.0027 (13)
C260.0727 (19)0.0670 (18)0.0366 (14)−0.0059 (15)−0.0168 (13)−0.0042 (13)
C270.0743 (19)0.0570 (16)0.0446 (15)0.0020 (15)−0.0213 (14)−0.0073 (13)
C280.0757 (19)0.0617 (17)0.0690 (18)−0.0042 (15)−0.0324 (16)−0.0025 (14)
C290.087 (2)0.095 (2)0.087 (2)−0.0045 (19)−0.0407 (18)−0.0270 (18)
C300.101 (3)0.114 (3)0.114 (3)−0.010 (2)−0.053 (2)−0.032 (2)
C310.089 (3)0.102 (3)0.119 (3)−0.003 (2)−0.052 (2)−0.008 (2)
C320.086 (3)0.106 (3)0.113 (3)0.003 (2)−0.032 (2)−0.027 (2)
C330.093 (2)0.091 (2)0.094 (2)0.0031 (19)−0.035 (2)−0.0286 (19)
C340.070 (2)0.089 (2)0.0533 (19)−0.0045 (18)−0.0156 (16)−0.0017 (17)
C350.084 (2)0.0686 (18)0.0595 (18)−0.0156 (16)−0.0249 (16)0.0062 (15)
C360.070 (2)0.0692 (19)0.083 (2)0.0011 (16)−0.0373 (17)−0.0032 (16)
C370.079 (2)0.078 (2)0.093 (2)0.0077 (18)−0.0316 (19)−0.0208 (19)
C380.105 (3)0.072 (2)0.108 (3)0.003 (2)−0.047 (2)−0.019 (2)
C390.089 (2)0.0624 (19)0.105 (3)−0.0099 (18)−0.048 (2)−0.0024 (18)
C400.078 (2)0.0641 (19)0.090 (2)−0.0140 (16)−0.0344 (18)0.0059 (17)
C410.096 (4)0.152 (5)0.155 (5)0.024 (3)−0.015 (3)−0.067 (4)
C420.142 (4)0.089 (3)0.162 (5)−0.040 (3)−0.077 (4)0.000 (3)
C430.0455 (14)0.0388 (13)0.0641 (16)−0.0054 (11)−0.0290 (13)−0.0019 (12)
C440.0506 (15)0.0379 (13)0.0588 (16)−0.0049 (11)−0.0288 (13)−0.0010 (11)
C450.0507 (15)0.0407 (13)0.0606 (16)−0.0087 (11)−0.0253 (12)−0.0003 (11)
C460.0511 (15)0.0352 (12)0.0676 (17)−0.0045 (11)−0.0304 (13)−0.0046 (12)
C470.0546 (16)0.0375 (13)0.0642 (17)0.0002 (12)−0.0332 (14)−0.0073 (12)
C480.0488 (15)0.0424 (14)0.0599 (16)−0.0047 (12)−0.0238 (13)−0.0020 (12)
C490.0592 (16)0.0489 (14)0.0597 (16)−0.0138 (12)−0.0302 (13)−0.0019 (12)
C500.073 (2)0.086 (2)0.074 (2)−0.0092 (17)−0.0258 (17)−0.0241 (17)
C510.098 (3)0.085 (2)0.072 (2)−0.020 (2)−0.0243 (19)−0.0259 (18)
C520.118 (3)0.086 (2)0.068 (2)−0.012 (2)−0.042 (2)−0.0094 (18)
C530.095 (3)0.118 (3)0.081 (2)0.004 (2)−0.057 (2)−0.016 (2)
C540.0678 (19)0.086 (2)0.0661 (18)0.0032 (16)−0.0348 (16)−0.0106 (16)
C550.067 (2)0.0528 (17)0.071 (2)−0.0017 (14)−0.0328 (16)−0.0148 (14)
C560.0582 (16)0.0414 (14)0.0776 (18)−0.0100 (12)−0.0335 (14)−0.0054 (13)
C570.0646 (17)0.0523 (15)0.0641 (17)−0.0143 (13)−0.0231 (14)−0.0064 (13)
C580.0635 (19)0.0571 (17)0.078 (2)−0.0057 (15)−0.0186 (16)−0.0125 (15)
C590.0561 (18)0.0654 (19)0.090 (2)−0.0106 (15)−0.0238 (17)−0.0035 (17)
C600.0588 (18)0.0593 (17)0.085 (2)−0.0185 (14)−0.0322 (16)−0.0022 (15)
C610.0570 (17)0.0498 (15)0.0788 (19)−0.0168 (13)−0.0296 (15)−0.0069 (14)
C620.092 (3)0.106 (3)0.109 (3)−0.001 (2)−0.015 (3)−0.047 (3)
C630.069 (2)0.094 (3)0.137 (4)−0.025 (2)−0.050 (2)−0.020 (2)

Geometric parameters (Å, °)

O1—C11.370 (3)C30—H30B0.9700
O1—H10.8200C31—C321.488 (6)
O2—C221.367 (4)C31—H31A0.9700
O2—H20.8200C31—H31B0.9700
O3—C431.366 (3)C32—C331.521 (6)
O3—H30.8200C32—H32A0.9700
N1—C151.466 (3)C32—H32B0.9700
N1—C191.467 (4)C33—H33A0.9700
N1—C141.486 (4)C33—H33B0.9700
N2—C361.462 (4)C34—H34A0.9600
N2—C401.478 (4)C34—H34B0.9600
N2—C351.480 (4)C34—H34C0.9600
N3—C571.467 (4)C35—H35A0.9700
N3—C611.471 (3)C35—H35B0.9700
N3—C561.482 (4)C36—C371.509 (5)
C1—C61.386 (4)C36—H36A0.9700
C1—C21.399 (4)C36—H36B0.9700
C2—C31.383 (4)C37—C381.502 (6)
C2—C71.507 (4)C37—C411.523 (6)
C3—C41.389 (4)C37—H370.9800
C3—H3A0.9300C38—C391.519 (6)
C4—C51.397 (4)C38—H38A0.9700
C4—C141.507 (4)C38—H38B0.9700
C5—C61.374 (4)C39—C401.503 (5)
C5—C131.505 (4)C39—C421.522 (6)
C6—H60.9300C39—H390.9800
C7—C81.447 (5)C40—H40A0.9700
C7—C121.478 (5)C40—H40B0.9700
C7—H70.9800C41—H41A0.9600
C8—C91.518 (7)C41—H41B0.9600
C8—H8A0.9700C41—H41C0.9600
C8—H8B0.9700C42—H42A0.9600
C9—C101.398 (7)C42—H42B0.9600
C9—H9A0.9700C42—H42C0.9600
C9—H9B0.9700C43—C481.386 (4)
C10—C111.415 (7)C43—C441.392 (4)
C10—H10A0.9700C44—C451.387 (4)
C10—H10B0.9700C44—C491.515 (4)
C11—C121.521 (6)C45—C461.391 (4)
C11—H11A0.9700C45—H450.9300
C11—H11B0.9700C46—C471.402 (4)
C12—H12A0.9700C46—C561.503 (4)
C12—H12B0.9700C47—C481.386 (4)
C13—H13A0.9600C47—C551.511 (4)
C13—H13B0.9600C48—H480.9300
C13—H13C0.9600C49—C541.517 (4)
C14—H14A0.9700C49—C501.524 (5)
C14—H14B0.9700C49—H490.9800
C15—C161.520 (4)C50—C511.529 (5)
C15—H15A0.9700C50—H50A0.9700
C15—H15B0.9700C50—H50B0.9700
C16—C171.517 (4)C51—C521.503 (6)
C16—C201.520 (4)C51—H51A0.9700
C16—H160.9800C51—H51B0.9700
C17—C181.515 (4)C52—C531.498 (6)
C17—H17A0.9700C52—H52A0.9700
C17—H17B0.9700C52—H52B0.9700
C18—C191.517 (4)C53—C541.520 (5)
C18—C211.526 (5)C53—H53A0.9700
C18—H180.9800C53—H53B0.9700
C19—H19A0.9700C54—H54A0.9700
C19—H19B0.9700C54—H54B0.9700
C20—H20A0.9600C55—H55A0.9600
C20—H20B0.9600C55—H55B0.9600
C20—H20C0.9600C55—H55C0.9600
C21—H21A0.9600C56—H56A0.9700
C21—H21B0.9600C56—H56B0.9700
C21—H21C0.9600C57—C581.522 (4)
C22—C271.383 (5)C57—H57A0.9700
C22—C231.397 (4)C57—H57B0.9700
C23—C241.386 (5)C58—C591.515 (5)
C23—C281.500 (5)C58—C621.527 (5)
C24—C251.394 (5)C58—H580.9800
C24—H240.9300C59—C601.512 (5)
C25—C261.407 (4)C59—H59A0.9700
C25—C351.505 (5)C59—H59B0.9700
C26—C271.383 (5)C60—C631.518 (4)
C26—C341.503 (5)C60—C611.526 (4)
C27—H270.9300C60—H600.9800
C28—C291.509 (5)C61—H61A0.9700
C28—C331.527 (5)C61—H61B0.9700
C28—H280.9800C62—H62A0.9600
C29—C301.516 (6)C62—H62B0.9600
C29—H29A0.9700C62—H62C0.9600
C29—H29B0.9700C63—H63A0.9600
C30—C311.488 (6)C63—H63B0.9600
C30—H30A0.9700C63—H63C0.9600
C1—O1—H1109.5C32—C33—C28111.8 (4)
C22—O2—H2109.5C32—C33—H33A109.2
C43—O3—H3109.5C28—C33—H33A109.2
C15—N1—C19109.5 (2)C32—C33—H33B109.2
C15—N1—C14110.7 (2)C28—C33—H33B109.2
C19—N1—C14109.7 (2)H33A—C33—H33B107.9
C36—N2—C40109.1 (3)C26—C34—H34A109.5
C36—N2—C35111.3 (3)C26—C34—H34B109.5
C40—N2—C35109.5 (3)H34A—C34—H34B109.5
C57—N3—C61109.7 (2)C26—C34—H34C109.5
C57—N3—C56111.1 (2)H34A—C34—H34C109.5
C61—N3—C56108.9 (2)H34B—C34—H34C109.5
O1—C1—C6121.5 (3)N2—C35—C25113.4 (3)
O1—C1—C2118.4 (3)N2—C35—H35A108.9
C6—C1—C2120.1 (3)C25—C35—H35A108.9
C3—C2—C1116.1 (3)N2—C35—H35B108.9
C3—C2—C7122.7 (3)C25—C35—H35B108.9
C1—C2—C7121.2 (3)H35A—C35—H35B107.7
C2—C3—C4124.4 (3)N2—C36—C37111.4 (3)
C2—C3—H3A117.8N2—C36—H36A109.3
C4—C3—H3A117.8C37—C36—H36A109.3
C3—C4—C5118.0 (3)N2—C36—H36B109.3
C3—C4—C14120.6 (3)C37—C36—H36B109.3
C5—C4—C14121.4 (3)H36A—C36—H36B108.0
C6—C5—C4118.5 (3)C38—C37—C36110.2 (4)
C6—C5—C13119.2 (3)C38—C37—C41112.1 (4)
C4—C5—C13122.3 (3)C36—C37—C41110.9 (4)
C5—C6—C1122.5 (3)C38—C37—H37107.8
C5—C6—H6118.7C36—C37—H37107.8
C1—C6—H6118.7C41—C37—H37107.8
C8—C7—C12107.5 (4)C37—C38—C39112.2 (3)
C8—C7—C2113.5 (3)C37—C38—H38A109.2
C12—C7—C2115.8 (3)C39—C38—H38A109.2
C8—C7—H7106.5C37—C38—H38B109.2
C12—C7—H7106.5C39—C38—H38B109.2
C2—C7—H7106.5H38A—C38—H38B107.9
C7—C8—C9113.2 (4)C40—C39—C38109.8 (3)
C7—C8—H8A108.9C40—C39—C42110.9 (4)
C9—C8—H8A108.9C38—C39—C42113.0 (4)
C7—C8—H8B108.9C40—C39—H39107.7
C9—C8—H8B108.9C38—C39—H39107.7
H8A—C8—H8B107.8C42—C39—H39107.7
C10—C9—C8116.2 (5)N2—C40—C39113.3 (3)
C10—C9—H9A108.2N2—C40—H40A108.9
C8—C9—H9A108.2C39—C40—H40A108.9
C10—C9—H9B108.2N2—C40—H40B108.9
C8—C9—H9B108.2C39—C40—H40B108.9
H9A—C9—H9B107.4H40A—C40—H40B107.7
C9—C10—C11113.6 (5)C37—C41—H41A109.5
C9—C10—H10A108.9C37—C41—H41B109.5
C11—C10—H10A108.9H41A—C41—H41B109.5
C9—C10—H10B108.9C37—C41—H41C109.5
C11—C10—H10B108.9H41A—C41—H41C109.5
H10A—C10—H10B107.7H41B—C41—H41C109.5
C10—C11—C12112.2 (4)C39—C42—H42A109.5
C10—C11—H11A109.2C39—C42—H42B109.5
C12—C11—H11A109.2H42A—C42—H42B109.5
C10—C11—H11B109.2C39—C42—H42C109.5
C12—C11—H11B109.2H42A—C42—H42C109.5
H11A—C11—H11B107.9H42B—C42—H42C109.5
C7—C12—C11113.2 (4)O3—C43—C48120.9 (3)
C7—C12—H12A108.9O3—C43—C44118.5 (2)
C11—C12—H12A108.9C48—C43—C44120.6 (2)
C7—C12—H12B108.9C45—C44—C43116.6 (3)
C11—C12—H12B108.9C45—C44—C49122.9 (3)
H12A—C12—H12B107.7C43—C44—C49120.5 (2)
C5—C13—H13A109.5C44—C45—C46123.8 (3)
C5—C13—H13B109.5C44—C45—H45118.1
H13A—C13—H13B109.5C46—C45—H45118.1
C5—C13—H13C109.5C45—C46—C47118.4 (2)
H13A—C13—H13C109.5C45—C46—C56119.9 (3)
H13B—C13—H13C109.5C47—C46—C56121.7 (3)
N1—C14—C4112.9 (2)C48—C47—C46118.2 (3)
N1—C14—H14A109.0C48—C47—C55119.0 (3)
C4—C14—H14A109.0C46—C47—C55122.8 (3)
N1—C14—H14B109.0C47—C48—C43122.1 (3)
C4—C14—H14B109.0C47—C48—H48119.0
H14A—C14—H14B107.8C43—C48—H48119.0
N1—C15—C16112.5 (2)C44—C49—C54110.1 (2)
N1—C15—H15A109.1C44—C49—C50114.7 (2)
C16—C15—H15A109.1C54—C49—C50109.6 (3)
N1—C15—H15B109.1C44—C49—H49107.4
C16—C15—H15B109.1C54—C49—H49107.4
H15A—C15—H15B107.8C50—C49—H49107.4
C17—C16—C20112.2 (3)C49—C50—C51111.3 (3)
C17—C16—C15109.4 (2)C49—C50—H50A109.4
C20—C16—C15111.2 (2)C51—C50—H50A109.4
C17—C16—H16108.0C49—C50—H50B109.4
C20—C16—H16108.0C51—C50—H50B109.4
C15—C16—H16108.0H50A—C50—H50B108.0
C18—C17—C16112.4 (2)C52—C51—C50111.3 (3)
C18—C17—H17A109.1C52—C51—H51A109.4
C16—C17—H17A109.1C50—C51—H51A109.4
C18—C17—H17B109.1C52—C51—H51B109.4
C16—C17—H17B109.1C50—C51—H51B109.4
H17A—C17—H17B107.8H51A—C51—H51B108.0
C17—C18—C19110.4 (2)C53—C52—C51111.6 (3)
C17—C18—C21111.4 (3)C53—C52—H52A109.3
C19—C18—C21110.5 (3)C51—C52—H52A109.3
C17—C18—H18108.1C53—C52—H52B109.3
C19—C18—H18108.1C51—C52—H52B109.3
C21—C18—H18108.1H52A—C52—H52B108.0
N1—C19—C18112.3 (2)C52—C53—C54112.2 (3)
N1—C19—H19A109.1C52—C53—H53A109.2
C18—C19—H19A109.1C54—C53—H53A109.2
N1—C19—H19B109.1C52—C53—H53B109.2
C18—C19—H19B109.1C54—C53—H53B109.2
H19A—C19—H19B107.9H53A—C53—H53B107.9
C16—C20—H20A109.5C49—C54—C53111.3 (3)
C16—C20—H20B109.5C49—C54—H54A109.4
H20A—C20—H20B109.5C53—C54—H54A109.4
C16—C20—H20C109.5C49—C54—H54B109.4
H20A—C20—H20C109.5C53—C54—H54B109.4
H20B—C20—H20C109.5H54A—C54—H54B108.0
C18—C21—H21A109.5C47—C55—H55A109.5
C18—C21—H21B109.5C47—C55—H55B109.5
H21A—C21—H21B109.5H55A—C55—H55B109.5
C18—C21—H21C109.5C47—C55—H55C109.5
H21A—C21—H21C109.5H55A—C55—H55C109.5
H21B—C21—H21C109.5H55B—C55—H55C109.5
O2—C22—C27121.6 (3)N3—C56—C46113.9 (2)
O2—C22—C23118.3 (3)N3—C56—H56A108.8
C27—C22—C23120.1 (3)C46—C56—H56A108.8
C24—C23—C22116.2 (3)N3—C56—H56B108.8
C24—C23—C28123.7 (3)C46—C56—H56B108.8
C22—C23—C28120.1 (3)H56A—C56—H56B107.7
C23—C24—C25124.4 (3)N3—C57—C58112.3 (2)
C23—C24—H24117.8N3—C57—H57A109.2
C25—C24—H24117.8C58—C57—H57A109.2
C24—C25—C26118.1 (3)N3—C57—H57B109.2
C24—C25—C35120.1 (3)C58—C57—H57B109.2
C26—C25—C35121.8 (3)H57A—C57—H57B107.9
C27—C26—C25117.6 (3)C59—C58—C57109.6 (3)
C27—C26—C34119.5 (3)C59—C58—C62112.7 (3)
C25—C26—C34122.9 (3)C57—C58—C62110.5 (3)
C26—C27—C22123.2 (3)C59—C58—H58108.0
C26—C27—H27118.4C57—C58—H58108.0
C22—C27—H27118.4C62—C58—H58108.0
C23—C28—C29111.5 (3)C60—C59—C58112.2 (3)
C23—C28—C33114.8 (3)C60—C59—H59A109.2
C29—C28—C33109.4 (3)C58—C59—H59A109.2
C23—C28—H28106.9C60—C59—H59B109.2
C29—C28—H28106.9C58—C59—H59B109.2
C33—C28—H28106.9H59A—C59—H59B107.9
C28—C29—C30113.1 (3)C59—C60—C63113.2 (3)
C28—C29—H29A108.9C59—C60—C61109.9 (3)
C30—C29—H29A108.9C63—C60—C61109.9 (3)
C28—C29—H29B108.9C59—C60—H60107.9
C30—C29—H29B108.9C63—C60—H60107.9
H29A—C29—H29B107.8C61—C60—H60107.9
C31—C30—C29113.5 (4)N3—C61—C60112.5 (2)
C31—C30—H30A108.9N3—C61—H61A109.1
C29—C30—H30A108.9C60—C61—H61A109.1
C31—C30—H30B108.9N3—C61—H61B109.1
C29—C30—H30B108.9C60—C61—H61B109.1
H30A—C30—H30B107.7H61A—C61—H61B107.8
C32—C31—C30111.2 (4)C58—C62—H62A109.5
C32—C31—H31A109.4C58—C62—H62B109.5
C30—C31—H31A109.4H62A—C62—H62B109.5
C32—C31—H31B109.4C58—C62—H62C109.5
C30—C31—H31B109.4H62A—C62—H62C109.5
H31A—C31—H31B108.0H62B—C62—H62C109.5
C31—C32—C33111.4 (4)C60—C63—H63A109.5
C31—C32—H32A109.3C60—C63—H63B109.5
C33—C32—H32A109.3H63A—C63—H63B109.5
C31—C32—H32B109.3C60—C63—H63C109.5
C33—C32—H32B109.3H63A—C63—H63C109.5
H32A—C32—H32B108.0H63B—C63—H63C109.5
O1—C1—C2—C3173.8 (2)C28—C29—C30—C31−51.8 (6)
C6—C1—C2—C3−7.2 (4)C29—C30—C31—C3252.4 (6)
O1—C1—C2—C7−5.6 (4)C30—C31—C32—C33−55.0 (6)
C6—C1—C2—C7173.4 (3)C31—C32—C33—C2857.5 (5)
C1—C2—C3—C42.7 (4)C23—C28—C33—C32179.1 (3)
C7—C2—C3—C4−178.0 (3)C29—C28—C33—C32−54.8 (5)
C2—C3—C4—C54.0 (4)C36—N2—C35—C2571.5 (4)
C2—C3—C4—C14−174.4 (3)C40—N2—C35—C25−167.8 (3)
C3—C4—C5—C6−6.1 (4)C24—C25—C35—N2−92.3 (4)
C14—C4—C5—C6172.3 (2)C26—C25—C35—N285.6 (4)
C3—C4—C5—C13172.5 (3)C40—N2—C36—C3760.0 (4)
C14—C4—C5—C13−9.0 (4)C35—N2—C36—C37−179.1 (3)
C4—C5—C6—C11.7 (4)N2—C36—C37—C38−58.3 (4)
C13—C5—C6—C1−177.0 (2)N2—C36—C37—C41177.0 (4)
O1—C1—C6—C5−175.8 (2)C36—C37—C38—C3953.4 (4)
C2—C1—C6—C55.3 (4)C41—C37—C38—C39177.4 (4)
C3—C2—C7—C8100.7 (4)C37—C38—C39—C40−51.1 (5)
C1—C2—C7—C8−79.9 (4)C37—C38—C39—C42−175.4 (4)
C3—C2—C7—C12−24.4 (5)C36—N2—C40—C39−58.8 (4)
C1—C2—C7—C12155.0 (4)C35—N2—C40—C39179.2 (3)
C12—C7—C8—C9−51.9 (6)C38—C39—C40—N254.1 (4)
C2—C7—C8—C9178.7 (4)C42—C39—C40—N2179.6 (3)
C7—C8—C9—C1049.2 (8)O3—C43—C44—C45−176.3 (2)
C8—C9—C10—C11−45.8 (9)C48—C43—C44—C454.2 (4)
C9—C10—C11—C1247.8 (8)O3—C43—C44—C494.8 (4)
C8—C7—C12—C1155.9 (6)C48—C43—C44—C49−174.7 (2)
C2—C7—C12—C11−176.0 (4)C43—C44—C45—C460.5 (4)
C10—C11—C12—C7−54.8 (7)C49—C44—C45—C46179.4 (2)
C15—N1—C14—C4−74.1 (3)C44—C45—C46—C47−4.9 (4)
C19—N1—C14—C4164.9 (2)C44—C45—C46—C56175.1 (2)
C3—C4—C14—N196.3 (3)C45—C46—C47—C484.6 (4)
C5—C4—C14—N1−82.1 (3)C56—C46—C47—C48−175.4 (2)
C19—N1—C15—C16−60.2 (3)C45—C46—C47—C55−176.1 (2)
C14—N1—C15—C16178.7 (2)C56—C46—C47—C553.9 (4)
N1—C15—C16—C1756.6 (3)C46—C47—C48—C43−0.1 (4)
N1—C15—C16—C20−178.9 (2)C55—C47—C48—C43−179.5 (2)
C20—C16—C17—C18−175.8 (3)O3—C43—C48—C47176.0 (2)
C15—C16—C17—C18−51.9 (3)C44—C43—C48—C47−4.5 (4)
C16—C17—C18—C1951.5 (3)C45—C44—C49—C54−95.5 (3)
C16—C17—C18—C21174.7 (3)C43—C44—C49—C5483.3 (3)
C15—N1—C19—C1859.1 (3)C45—C44—C49—C5028.6 (4)
C14—N1—C19—C18−179.2 (2)C43—C44—C49—C50−152.6 (3)
C17—C18—C19—N1−55.0 (3)C44—C49—C50—C51179.0 (3)
C21—C18—C19—N1−178.8 (3)C54—C49—C50—C51−56.6 (4)
O2—C22—C23—C24−176.5 (3)C49—C50—C51—C5256.0 (5)
C27—C22—C23—C243.8 (4)C50—C51—C52—C53−54.2 (5)
O2—C22—C23—C282.9 (4)C51—C52—C53—C5454.2 (5)
C27—C22—C23—C28−176.7 (3)C44—C49—C54—C53−176.8 (3)
C22—C23—C24—C251.4 (5)C50—C49—C54—C5356.2 (4)
C28—C23—C24—C25−178.0 (3)C52—C53—C54—C49−55.7 (5)
C23—C24—C25—C26−5.3 (5)C57—N3—C56—C4673.1 (3)
C23—C24—C25—C35172.7 (3)C61—N3—C56—C46−166.0 (3)
C24—C25—C26—C273.8 (4)C45—C46—C56—N3−92.0 (3)
C35—C25—C26—C27−174.2 (3)C47—C46—C56—N388.0 (3)
C24—C25—C26—C34−177.0 (3)C61—N3—C57—C5859.3 (3)
C35—C25—C26—C345.0 (4)C56—N3—C57—C58179.7 (2)
C25—C26—C27—C221.3 (4)N3—C57—C58—C59−56.7 (4)
C34—C26—C27—C22−177.9 (3)N3—C57—C58—C62178.5 (3)
O2—C22—C27—C26175.1 (3)C57—C58—C59—C6053.2 (4)
C23—C22—C27—C26−5.3 (4)C62—C58—C59—C60176.7 (3)
C24—C23—C28—C29−92.1 (4)C58—C59—C60—C63−175.8 (3)
C22—C23—C28—C2988.5 (4)C58—C59—C60—C61−52.5 (4)
C24—C23—C28—C3333.0 (5)C57—N3—C61—C60−58.6 (3)
C22—C23—C28—C33−146.4 (3)C56—N3—C61—C60179.7 (3)
C23—C28—C29—C30179.8 (3)C59—C60—C61—N355.3 (4)
C33—C28—C29—C3051.7 (5)C63—C60—C61—N3−179.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.032.843 (3)170
C13—H13B···O1i0.962.523.335 (4)143
O2—H2···N2ii0.822.032.845 (3)171
C34—H34C···O2ii0.962.493.348 (4)149
O3—H3···N3iii0.822.022.831 (3)174
C55—H55C···O3iii0.962.583.404 (4)145

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2466).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, Y. S., Cao, G. K., Peng, S. X., Dai, D. Z. & Jin, L. (1986). Acta Pharm. Sin.21, 265–272.

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