Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1181
doi:10.1107/S1600536808015717

t-3-Benzyl-r-2,c-6-bis­­(4-meth­oxy­phen­yl)­piperidin-4-one

J. Jayabharathi,a A. Thangamani,a S. Balamurugan,b A. Thiruvalluvarb* and A. Lindenc

aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, and cInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
*Correspondence e-mail: athiru@vsnl.net

(Received 22 May 2008; accepted 25 May 2008; online 7 June 2008)

In the title compound, C26H27NO3, the piperidine ring adopts a chair conformation. The two methoxy­phenyl groups attached to the piperidine ring at positions 2 and 6 have equatorial orientations and make a dihedral angle of 87.33 (8)°. The benzyl group at position 3 has an equatorial orientation. The phenyl ring of the benzyl group makes dihedral angles of 75.60 (9) and 73.69 (9)° with the two benzene rings. Mol­ecules are linked by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds and by C—H⋯π inter­actions.

Related literature

For related literature, see: Jayabharathi et al. (2007[Jayabharathi, J., Manimekalai, A., Consalata Vani, T. & Padmavathy, M. (2007). Eur. J. Med. Chem. 42, 593-605.]); Thiruvalluvar et al. (2007[Thiruvalluvar, A., Balamurugan, S., Butcher, R. J., Manimekalai, A. & Jayabharathi, J. (2007). Acta Cryst. E63, o4533.]); Noller & Baliah (1948[Noller, C. R. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853-3855.]).

[Scheme 1]

Experimental

Crystal data

  • C26H27NO3

  • Mr = 401.49

  • Triclinic, [P \overline 1]

  • a = 5.5612 (2) Å

  • b = 13.8097 (5) Å

  • c = 14.5119 (6) Å

  • α = 71.629 (2)°

  • β = 79.928 (2)°

  • γ = 82.526 (2)°

  • V = 1038.04 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 160 (1) K

  • 0.30 × 0.18 × 0.13 mm
Data collection

  • Nonius KappaCCD area-detector diffractometer

  • Absorption correction: none

  • 25390 measured reflections

  • 4740 independent reflections

  • 3325 reflections with I > 2σ(I)

  • Rint = 0.052
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.177

  • S = 1.09

  • 4740 reflections

  • 275 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.92 (2) 2.56 (2) 3.420 (2) 154.9 (14)
C5—H5B⋯O4ii 0.99 2.51 3.490 (2) 173
C16—H16B⋯Cg1iii 0.98 2.85 3.659 (2) 140
C16—H16C⋯Cg2iv 0.98 2.98 3.587 (2) 121
C34—H34⋯Cg3v 0.95 2.91 3.719 (2) 144
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z; (iii) x+1, y, z; (iv) -x+2, -y+1, -z; (v) -x, -y+1, -z+1. Cg1, Cg2 and Cg3 are the centroids of the C61–C66, C31–C36 and C21–26 rings, respectively.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. London: Academic Press.]); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. London: Academic Press.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015717/wn2265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015717/wn2265Isup2.hkl

checkCIF report


Comment top

Jayabharathi et al. (2007) have reported the synthesis, stereochemistry and antimicrobial evaluation of t3-benzyl-r2,c6-diarylpiperidin- 4-one and its derivatives. Thiruvalluvar et al. (2007) have reported the crystal structure of t3-benzyl-1-formyl-r2,c-6-diphenylpiperidin-4-one, in which the piperidine ring is in a distorted boat form.

In the title compound, (Fig. 1), the piperidine ring adopts a chair conformation. The two methoxyphenyl groups attached to the piperidine ring at positions 2 and 6 have equatorial orientations, and make a dihedral angle of 87.33 (8)°. The benzyl group at position 3 has an equatorial orientation. The phenyl ring of the benzyl group makes a dihedral angle of 75.60 (9)° with the benzene ring at C2, and 73.69 (9)° with the benzene ring at C6. Molecules are linked by intermolecular N1—H1···O2 and C5—H5B···O4 hydrogen bonds (Fig. 2). There are C16—H16B···π (1 + x, y, z) interactions involving the benzene ring at C6, C16—H16C···π (2 - x, 1 - y, -z) interactions involving the phenyl ring at C13 and C34—H34···π (-x, 1 - y, 1 - z) interactions involving the benzene ring at C2.

Related literature top

For related literature, see: Jayabharathi et al. (2007); Thiruvalluvar et al. (2007); Noller & Baliah (1948). Cg1, Cg2 and Cg3 are the centroids of the C61–C66, C31–C36 and C21–26 rings.

Experimental top

The title compound was prepared according to the literature procedure (Noller & Baliah, 1948). A mixture of ammonium acetate (0.1 mol, 7.7 g), redistilled 4-methoxybenzaldehyde (0.2 mol, 24.3 ml) and benzylacetone (0.1 mol, 15 ml) in distilled ethanol was heated to boiling. The mixture was cooled and 10 ml hydrochloric acid was added. The precipitated 3-benzyl-r2,c6-bis(p-methoxyphenyl)piperidin-4-one hydrochlorides were treated with aqueous ammonia and diluted with water. The separated solid was filtered off and recrystallized from ethanol. The yield of the isolated pure product was 10.5 g (70%).

Refinement top

The H atom bonded to N1 was located in a difference Fourier map and refined isotropically to an N—H bond length of 0.92 (2) Å. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–1.00 Å and Uiso(H) = xUeq(carrier atom), where x = 1.5 for methyl and 1.2 for all other C atoms.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. The molecular 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.
t-3-Benzyl-r-2,c-6-bis(4-methoxyphenyl)piperidin-4-one top
Crystal data top
C26H27NO3Z = 2
Mr = 401.49F(000) = 428
Triclinic, P1Dx = 1.285 Mg m−3
Hall symbol: -P 1Melting point: 471 K
a = 5.5612 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.8097 (5) ÅCell parameters from 4566 reflections
c = 14.5119 (6) Åθ = 2.0–27.5°
α = 71.629 (2)°µ = 0.08 mm−1
β = 79.928 (2)°T = 160 K
γ = 82.526 (2)°Prism, colourless
V = 1038.04 (7) Å30.30 × 0.18 × 0.13 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer		3325 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.052
Horizontally mounted graphite crystal monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 9 pixels mm-1h = −7→7
ϕ and ω scans with κ offsetsk = −17→17
25390 measured reflectionsl = −17→18
4740 independent reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.1039P)2 + 0.0262P]
where P = (Fo2 + 2Fc2)/3
4740 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
C26H27NO3γ = 82.526 (2)°
Mr = 401.49V = 1038.04 (7) Å3
Triclinic, P1Z = 2
a = 5.5612 (2) ÅMo Kα radiation
b = 13.8097 (5) ŵ = 0.08 mm−1
c = 14.5119 (6) ÅT = 160 K
α = 71.629 (2)°0.30 × 0.18 × 0.13 mm
β = 79.928 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer		3325 reflections with I > 2σ(I)
25390 measured reflectionsRint = 0.052
4740 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.177H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.28 e Å−3
4740 reflectionsΔρmin = −0.32 e Å−3
275 parameters
Special details top

Experimental. Solvent used:Ethanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.788 (2) Frames collected: 372 Seconds exposure per frame: 40 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 32.0

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 > 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
O20.3480 (3)0.01839 (10)0.69755 (9)0.0380 (4)
O40.2802 (3)0.48862 (10)0.13605 (9)0.0404 (4)
O61.5838 (2)0.14802 (10)−0.07836 (10)0.0409 (5)
N10.7126 (3)0.23805 (11)0.24454 (10)0.0265 (5)
C20.4629 (3)0.25237 (12)0.29523 (12)0.0245 (5)
C30.4009 (3)0.36832 (12)0.28311 (12)0.0250 (5)
C40.4384 (3)0.42694 (12)0.17505 (12)0.0279 (5)
C50.6790 (3)0.40193 (13)0.11763 (12)0.0301 (5)
C60.7249 (3)0.28549 (13)0.13751 (12)0.0273 (5)
C120.5115 (5)0.0257 (2)0.75990 (16)0.0691 (10)
C130.1459 (3)0.39167 (13)0.33331 (13)0.0279 (5)
C161.7542 (4)0.21784 (17)−0.14188 (14)0.0428 (7)
C210.4411 (3)0.18956 (12)0.40212 (12)0.0249 (5)
C220.2541 (3)0.12454 (12)0.44361 (12)0.0262 (5)
C230.2270 (3)0.06881 (12)0.54173 (12)0.0278 (5)
C240.3891 (3)0.07709 (12)0.60121 (12)0.0267 (5)
C250.5762 (3)0.14155 (13)0.56151 (13)0.0287 (5)
C260.6007 (3)0.19672 (12)0.46278 (12)0.0271 (5)
C310.0983 (3)0.49710 (12)0.34677 (12)0.0258 (5)
C320.2424 (3)0.52745 (13)0.40038 (13)0.0300 (6)
C330.1909 (4)0.62079 (14)0.41958 (13)0.0346 (6)
C34−0.0083 (4)0.68498 (14)0.38666 (14)0.0366 (6)
C35−0.1530 (3)0.65645 (14)0.33296 (15)0.0380 (6)
C36−0.0982 (3)0.56370 (14)0.31217 (14)0.0333 (6)
C610.9614 (3)0.25342 (13)0.08147 (12)0.0274 (5)
C621.1216 (3)0.32162 (14)0.01856 (13)0.0317 (6)
C631.3309 (3)0.29035 (14)−0.03643 (13)0.0326 (6)
C641.3824 (3)0.18795 (14)−0.02915 (13)0.0303 (6)
C651.2233 (4)0.11740 (14)0.03294 (14)0.0356 (6)
C661.0172 (3)0.14985 (14)0.08710 (13)0.0332 (6)
H10.750 (3)0.1682 (16)0.2598 (14)0.033 (5)*
H20.345310.229210.263230.0294*
H30.521280.390340.314730.0300*
H5A0.813710.428100.137040.0361*
H5B0.675130.435570.046670.0361*
H60.587250.261830.116190.0328*
H12A0.46528−0.019390.826360.1039*
H12B0.502640.096540.761440.1039*
H12C0.679120.005040.734860.1039*
H13A0.024100.383910.294370.0335*
H13B0.118820.340080.398580.0335*
H16A1.889150.17995−0.172370.0641*
H16B1.819210.25311−0.103720.0641*
H16C1.670910.26824−0.193010.0641*
H220.142460.118320.403550.0314*
H230.097730.024900.568540.0333*
H250.687320.147960.601690.0344*
H260.730090.240550.436000.0325*
H320.378580.483440.424280.0360*
H330.293030.640580.455480.0415*
H34−0.045590.748340.400850.0439*
H35−0.290420.700320.310130.0455*
H36−0.196600.545600.273760.0400*
H621.087910.392390.012590.0380*
H631.437640.33931−0.078790.0391*
H651.256460.046800.038050.0426*
H660.910400.100790.129280.0398*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0459 (8)0.0394 (8)0.0250 (7)−0.0122 (6)−0.0048 (6)−0.0012 (6)
O40.0440 (8)0.0385 (8)0.0300 (7)0.0116 (6)−0.0047 (6)−0.0042 (6)
O60.0350 (8)0.0445 (8)0.0406 (8)−0.0017 (6)0.0080 (6)−0.0169 (7)
N10.0293 (8)0.0239 (8)0.0234 (8)−0.0005 (6)−0.0018 (6)−0.0045 (6)
C20.0257 (9)0.0248 (9)0.0228 (8)−0.0035 (7)−0.0020 (7)−0.0069 (7)
C30.0257 (9)0.0245 (9)0.0248 (9)−0.0025 (7)−0.0035 (7)−0.0071 (7)
C40.0333 (10)0.0226 (9)0.0275 (9)−0.0031 (7)−0.0034 (8)−0.0073 (7)
C50.0342 (10)0.0293 (9)0.0229 (9)−0.0009 (8)−0.0003 (7)−0.0051 (7)
C60.0304 (10)0.0280 (9)0.0227 (9)−0.0022 (7)−0.0026 (7)−0.0070 (7)
C120.0737 (18)0.098 (2)0.0292 (11)−0.0421 (15)−0.0179 (12)0.0097 (12)
C130.0279 (10)0.0281 (9)0.0265 (9)−0.0027 (7)−0.0018 (7)−0.0075 (7)
C160.0341 (11)0.0567 (13)0.0335 (11)−0.0044 (9)0.0053 (9)−0.0130 (10)
C210.0264 (9)0.0209 (8)0.0269 (9)0.0004 (7)−0.0019 (7)−0.0084 (7)
C220.0282 (9)0.0240 (9)0.0277 (9)−0.0032 (7)−0.0034 (7)−0.0093 (7)
C230.0277 (10)0.0257 (9)0.0297 (9)−0.0066 (7)0.0004 (7)−0.0085 (7)
C240.0314 (10)0.0227 (9)0.0228 (8)−0.0007 (7)−0.0006 (7)−0.0046 (7)
C250.0302 (10)0.0264 (9)0.0298 (9)−0.0019 (7)−0.0065 (7)−0.0078 (7)
C260.0251 (9)0.0241 (9)0.0303 (9)−0.0040 (7)−0.0021 (7)−0.0060 (7)
C310.0242 (9)0.0259 (9)0.0233 (8)−0.0027 (7)0.0031 (7)−0.0051 (7)
C320.0284 (10)0.0315 (10)0.0288 (9)0.0007 (7)−0.0006 (7)−0.0101 (8)
C330.0383 (11)0.0351 (10)0.0317 (10)−0.0065 (8)0.0011 (8)−0.0135 (8)
C340.0406 (11)0.0273 (9)0.0400 (11)−0.0034 (8)0.0073 (9)−0.0142 (8)
C350.0299 (10)0.0301 (10)0.0483 (12)0.0038 (8)−0.0016 (9)−0.0085 (9)
C360.0276 (10)0.0346 (10)0.0376 (10)−0.0019 (8)−0.0040 (8)−0.0111 (8)
C610.0298 (10)0.0292 (9)0.0225 (8)−0.0010 (7)−0.0046 (7)−0.0067 (7)
C620.0357 (11)0.0293 (9)0.0289 (10)−0.0019 (8)−0.0018 (8)−0.0090 (8)
C630.0337 (10)0.0360 (10)0.0260 (9)−0.0078 (8)0.0017 (8)−0.0075 (8)
C640.0290 (10)0.0374 (10)0.0252 (9)0.0012 (8)−0.0025 (7)−0.0125 (8)
C650.0412 (11)0.0281 (9)0.0349 (10)−0.0006 (8)−0.0006 (8)−0.0093 (8)
C660.0342 (10)0.0292 (9)0.0317 (10)−0.0036 (8)0.0040 (8)−0.0071 (8)
Geometric parameters (Å, º) top
O2—C121.423 (3)C62—C631.393 (3)
O2—C241.373 (2)C63—C641.380 (3)
O4—C41.223 (2)C64—C651.391 (3)
O6—C161.432 (3)C65—C661.380 (3)
O6—C641.370 (2)C2—H21.0000
N1—C21.474 (2)C3—H31.0000
N1—C61.476 (2)C5—H5A0.9900
N1—H10.92 (2)C5—H5B0.9900
C2—C31.554 (2)C6—H61.0000
C2—C211.512 (2)C12—H12A0.9800
C3—C41.512 (2)C12—H12B0.9800
C3—C131.521 (2)C12—H12C0.9800
C4—C51.508 (2)C13—H13A0.9900
C5—C61.536 (3)C13—H13B0.9900
C6—C611.513 (2)C16—H16A0.9800
C13—C311.513 (3)C16—H16B0.9800
C21—C261.387 (2)C16—H16C0.9800
C21—C221.391 (2)C22—H220.9500
C22—C231.381 (2)C23—H230.9500
C23—C241.390 (2)C25—H250.9500
C24—C251.384 (2)C26—H260.9500
C25—C261.387 (2)C32—H320.9500
C31—C321.391 (2)C33—H330.9500
C31—C361.390 (3)C34—H340.9500
C32—C331.387 (3)C35—H350.9500
C33—C341.380 (3)C36—H360.9500
C34—C351.380 (3)C62—H620.9500
C35—C361.391 (3)C63—H630.9500
C61—C661.403 (3)C65—H650.9500
C61—C621.381 (2)C66—H660.9500
O4···C363.355 (2)H3···C262.8900
O4···C313.082 (2)H3···C322.7500
O6···C12i3.396 (3)H3···H262.5500
O2···H1ii2.56 (2)H3···H322.3200
O2···H66ii2.8000H5A···O4xii2.8200
O4···H5Aiii2.8200H5A···C622.8200
O4···H5Biv2.5100H5A···H622.2900
O4···H63v2.8400H5B···C622.8000
O4···H13A2.5900H5B···H622.3000
O6···H12Bi2.7600H5B···O4iv2.5100
O6···H65vi2.6300H6···C62iii3.0600
N1···H262.8100H6···C63iii2.7400
N1···H662.9000H6···C64iii3.0500
C12···O6vii3.396 (3)H6···H22.2600
C12···C65viii3.488 (3)H12A···C65viii2.8100
C13···C223.545 (3)H12A···H66ii2.3900
C16···C35v3.382 (3)H12B···O6vii2.7600
C16···C34v3.486 (3)H12B···C16vii3.0800
C22···C133.545 (3)H12B···C252.7400
C22···C24ii3.371 (2)H12B···H252.2900
C23···C24ii3.590 (2)H12C···C252.7300
C24···C22ii3.371 (2)H12C···H252.2800
C24···C23ii3.590 (2)H13A···O42.5900
C31···O43.082 (2)H13A···H362.3600
C31···C33ix3.468 (2)H13B···C212.5600
C32···C32ix3.553 (2)H13B···C222.8700
C32···C33ix3.540 (3)H13B···H26iii2.6000
C33···C31ix3.468 (2)H13B···C33ix3.0500
C33···C32ix3.540 (3)H13B···C34ix2.9900
C34···C16v3.486 (3)H16A···C34v3.0900
C35···C16v3.382 (3)H16A···C35v3.0100
C36···O43.355 (2)H16B···C61xii2.9300
C65···C12viii3.488 (3)H16B···C62xii3.0600
C3···H322.9400H16B···C632.7600
C3···H263.0800H16B···C66xii3.0100
C5···H622.5200H16B···H632.3200
C12···H66ii3.0200H16C···C632.7600
C12···H252.5100H16C···H632.3100
C16···H12Bi3.0800H16C···C34v3.0300
C16···H632.5300H22···H22.3300
C21···H13B2.5600H22···H23x2.4200
C22···H23x3.0900H23···C22x3.0900
C22···H13B2.8700H23···H22x2.4200
C23···H34ix2.9100H25···C122.5100
C24···H34ix2.8700H25···H12B2.2900
C25···H12B2.7400H25···H12C2.2800
C25···H12C2.7300H25···H34xi2.5900
C26···H33xi3.0100H26···N12.8100
C26···H32.8900H26···C33.0800
C26···H13.05 (2)H26···H32.5500
C32···H32.7500H26···H13Bxii2.6000
C33···H13Bix3.0500H26···H33xi2.5900
C34···H16Av3.0900H32···C32.9400
C34···H16Cv3.0300H32···H32.3200
C34···H13Bix2.9900H33···C26xi3.0100
C35···H16Av3.0100H33···H26xi2.5900
C61···H16Biii2.9300H34···C23ix2.9100
C62···H5A2.8200H34···C24ix2.8700
C62···H6xii3.0600H34···H25xi2.5900
C62···H16Biii3.0600H36···H13A2.3600
C62···H5B2.8000H62···C52.5200
C63···H6xii2.7400H62···H5A2.2900
C63···H16C2.7600H62···H5B2.3000
C63···H16B2.7600H63···C162.5300
C64···H6xii3.0500H63···H16B2.3200
C65···H12Aviii2.8100H63···H16C2.3100
C66···H12.748 (19)H63···O4v2.8400
C66···H16Biii3.0100H65···O6vi2.6300
H1···C263.05 (2)H66···N12.9000
H1···C662.748 (19)H66···H12.3600
H1···H662.3600H66···O2ii2.8000
H1···O2ii2.56 (2)H66···C12ii3.0200
H2···H62.2600H66···H12Aii2.3900
H2···H222.3300
C12—O2—C24116.63 (16)C13—C3—H3107.00
C16—O6—C64117.48 (16)C4—C5—H5A110.00
C2—N1—C6111.11 (14)C4—C5—H5B110.00
C2—N1—H1106.0 (11)C6—C5—H5A110.00
C6—N1—H1111.0 (12)C6—C5—H5B110.00
N1—C2—C3108.50 (14)H5A—C5—H5B108.00
N1—C2—C21110.89 (14)N1—C6—H6108.00
C3—C2—C21111.61 (14)C5—C6—H6108.00
C2—C3—C4108.85 (14)C61—C6—H6108.00
C4—C3—C13112.38 (14)O2—C12—H12A109.00
C2—C3—C13112.83 (14)O2—C12—H12B109.00
O4—C4—C5122.03 (15)O2—C12—H12C109.00
O4—C4—C3121.98 (15)H12A—C12—H12B109.00
C3—C4—C5115.96 (14)H12A—C12—H12C109.00
C4—C5—C6109.84 (14)H12B—C12—H12C109.00
N1—C6—C5107.86 (14)C3—C13—H13A108.00
C5—C6—C61113.46 (14)C3—C13—H13B108.00
N1—C6—C61112.45 (14)C31—C13—H13A108.00
C3—C13—C31115.19 (15)C31—C13—H13B108.00
C2—C21—C26121.64 (15)H13A—C13—H13B107.00
C22—C21—C26117.68 (15)O6—C16—H16A109.00
C2—C21—C22120.65 (15)O6—C16—H16B109.00
C21—C22—C23121.49 (16)O6—C16—H16C109.00
C22—C23—C24119.89 (16)H16A—C16—H16B109.00
O2—C24—C23115.62 (15)H16A—C16—H16C109.00
C23—C24—C25119.60 (15)H16B—C16—H16C109.00
O2—C24—C25124.79 (16)C21—C22—H22119.00
C24—C25—C26119.66 (16)C23—C22—H22119.00
C21—C26—C25121.68 (16)C22—C23—H23120.00
C32—C31—C36117.90 (16)C24—C23—H23120.00
C13—C31—C32120.30 (15)C24—C25—H25120.00
C13—C31—C36121.67 (16)C26—C25—H25120.00
C31—C32—C33121.20 (17)C21—C26—H26119.00
C32—C33—C34120.17 (19)C25—C26—H26119.00
C33—C34—C35119.51 (18)C31—C32—H32119.00
C34—C35—C36120.21 (17)C33—C32—H32119.00
C31—C36—C35120.98 (17)C32—C33—H33120.00
C62—C61—C66116.82 (16)C34—C33—H33120.00
C6—C61—C62123.61 (17)C33—C34—H34120.00
C6—C61—C66119.41 (15)C35—C34—H34120.00
C61—C62—C63122.34 (18)C34—C35—H35120.00
C62—C63—C64119.71 (17)C36—C35—H35120.00
O6—C64—C65115.68 (17)C31—C36—H36120.00
O6—C64—C63124.97 (16)C35—C36—H36120.00
C63—C64—C65119.34 (17)C61—C62—H62119.00
C64—C65—C66120.09 (18)C63—C62—H62119.00
C61—C66—C65121.70 (17)C62—C63—H63120.00
N1—C2—H2109.00C64—C63—H63120.00
C3—C2—H2109.00C64—C65—H65120.00
C21—C2—H2109.00C66—C65—H65120.00
C2—C3—H3108.00C61—C66—H66119.00
C4—C3—H3108.00C65—C66—H66119.00
C12—O2—C24—C23−179.92 (18)C3—C13—C31—C32−59.1 (2)
C12—O2—C24—C250.2 (3)C3—C13—C31—C36125.18 (18)
C16—O6—C64—C630.3 (3)C2—C21—C22—C23−178.11 (16)
C16—O6—C64—C65−179.06 (16)C26—C21—C22—C230.0 (3)
C6—N1—C2—C3−66.26 (17)C2—C21—C26—C25177.96 (16)
C6—N1—C2—C21170.83 (14)C22—C21—C26—C25−0.2 (3)
C2—N1—C6—C566.38 (17)C21—C22—C23—C24−0.1 (3)
C2—N1—C6—C61−167.76 (14)C22—C23—C24—O2−179.71 (16)
N1—C2—C3—C454.73 (17)C22—C23—C24—C250.2 (3)
N1—C2—C3—C13−179.81 (13)O2—C24—C25—C26179.58 (17)
C21—C2—C3—C4177.22 (14)C23—C24—C25—C26−0.3 (3)
C21—C2—C3—C13−57.32 (19)C24—C25—C26—C210.3 (3)
N1—C2—C21—C22−128.35 (17)C13—C31—C32—C33−175.30 (16)
N1—C2—C21—C2653.6 (2)C36—C31—C32—C330.6 (3)
C3—C2—C21—C22110.55 (18)C13—C31—C36—C35173.98 (17)
C3—C2—C21—C26−67.5 (2)C32—C31—C36—C35−1.8 (3)
C2—C3—C4—O4128.46 (18)C31—C32—C33—C341.0 (3)
C2—C3—C4—C5−49.42 (19)C32—C33—C34—C35−1.2 (3)
C13—C3—C4—O42.7 (2)C33—C34—C35—C360.0 (3)
C13—C3—C4—C5−175.14 (15)C34—C35—C36—C311.6 (3)
C2—C3—C13—C31165.03 (14)C6—C61—C62—C63−176.17 (16)
C4—C3—C13—C31−71.44 (19)C66—C61—C62—C63−0.7 (3)
O4—C4—C5—C6−127.52 (18)C6—C61—C66—C65176.14 (17)
C3—C4—C5—C650.36 (19)C62—C61—C66—C650.5 (3)
C4—C5—C6—N1−55.62 (18)C61—C62—C63—C640.4 (3)
C4—C5—C6—C61179.12 (14)C62—C63—C64—O6−179.03 (16)
N1—C6—C61—C62−122.67 (18)C62—C63—C64—C650.3 (3)
N1—C6—C61—C6662.0 (2)O6—C64—C65—C66178.87 (17)
C5—C6—C61—C620.1 (2)C63—C64—C65—C66−0.5 (3)
C5—C6—C61—C66−175.27 (15)C64—C65—C66—C610.1 (3)
Symmetry codes: (i) x+1, y, z−1; (ii) −x+1, −y, −z+1; (iii) x−1, y, z; (iv) −x+1, −y+1, −z; (v) −x+2, −y+1, −z; (vi) −x+3, −y, −z; (vii) x−1, y, z+1; (viii) −x+2, −y, −z+1; (ix) −x, −y+1, −z+1; (x) −x, −y, −z+1; (xi) −x+1, −y+1, −z+1; (xii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2ii0.92 (2)2.56 (2)3.420 (2)154.9 (14)
C5—H5B···O4iv0.992.513.490 (2)173
C16—H16B···Cg1xii0.982.853.659 (2)140
C16—H16C···Cg2v0.982.983.587 (2)121
C34—H34···Cg3ix0.952.913.719 (2)144
Symmetry codes: (ii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z; (v) −x+2, −y+1, −z; (ix) −x, −y+1, −z+1; (xii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC26H27NO3
Mr401.49
Crystal system, space groupTriclinic, P1
Temperature (K)160
a, b, c (Å)5.5612 (2), 13.8097 (5), 14.5119 (6)
α, β, γ (°)71.629 (2), 79.928 (2), 82.526 (2)
V (Å3)1038.04 (7)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.30 × 0.18 × 0.13
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		25390, 4740, 3325
Rint0.052
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.177, 1.09
No. of reflections4740
No. of parameters275
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.28, −0.32

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.92 (2)2.56 (2)3.420 (2)154.9 (14)
C5—H5B···O4ii0.992.513.490 (2)173
C16—H16B···Cg1iii0.982.853.659 (2)140
C16—H16C···Cg2iv0.982.983.587 (2)121
C34—H34···Cg3v0.952.913.719 (2)144
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) −x+2, −y+1, −z; (v) −x, −y+1, −z+1.
 

Acknowledgements

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].

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationJayabharathi, J., Manimekalai, A., Consalata Vani, T. & Padmavathy, M. (2007). Eur. J. Med. Chem. 42, 593–605.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationNoller, C. R. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853–3855.  CrossRef PubMed CAS Web of Science Google Scholar
 First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. London: Academic Press.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationThiruvalluvar, A., Balamurugan, S., Butcher, R. J., Manimekalai, A. & Jayabharathi, J. (2007). Acta Cryst. E63, o4533.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 7| July 2008| Page o1181
doi:10.1107/S1600536808015717
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS