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Acta Cryst. (2009). E65, o456    [ doi:10.1107/S1600536809001305 ]

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

G.-Y. Duan, F.-G. Guo and C.-C. Xia

Abstract top

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 [pi]-[pi] stacking interactions [centroid-centroid distance = 3.876 (2) Å].

Comment top

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,

Related literature top

For the biological activity: Zhang et al. (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 35% probability level.
2-Cyclohexyl-4-[(3,5-dimethylpiperidin-1-yl)methyl]-5-methylphenol top
Crystal data top
C21H33NOZ = 6
Mr = 315.48F(000) = 1044
Triclinic, P1Dx = 1.062 Mg m−3
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 mm−1
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 top
Bruker SMART CCD area-detector
diffractometer		6658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
graphiteθmax = 25.1°, θmin = 1.3°
φ and ω scansh = −13→14
15478 measured reflectionsk = −19→19
10326 independent reflectionsl = −19→15
Refinement top
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 = 1.03 w = 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 Å−3
1296 restraintsΔρmin = −0.60 e Å−3
Crystal data top
C21H33NOγ = 71.951 (1)°
Mr = 315.48V = 2958.6 (3) Å3
Triclinic, P1Z = 6
a = 12.0551 (7) ÅMo Kα radiation
b = 16.5513 (10) ŵ = 0.06 mm−1
c = 16.7371 (10) ÅT = 273 K
α = 78.969 (1)°0.18 × 0.15 × 0.12 mm
β = 69.354 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		6658 reflections with I > 2σ(I)
15478 measured reflectionsRint = 0.016
10326 independent reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.219Δρmax = 0.67 e Å−3
S = 1.03Δρmin = −0.60 e Å−3
10326 reflectionsAbsolute structure: ?
634 parametersFlack parameter: ?
1296 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
references
References top

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.

Zhang, Y. S., Cao, G. K., Peng, S. X., Dai, D. Z. & Jin, L. (1986). Acta Pharm. Sin. 21, 265–272.