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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1211.
Published online 2008 June 7. doi:  10.1107/S1600536808016449
PMCID: PMC2961741

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

Abstract

In the title mol­ecule, C26H28N2O3, 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 80.72 (15)°. The benzyl group at position 3 has an equatorial orientation. The oxime group at position 4 has a bi­sectional orientation. The ring of the benzyl group makes dihedral angles of 64.71 (16) and 84.79 (17)° with the two benzene rings. Mol­ecules are linked by inter­molecular N—H(...)O, O—H(...)N and C—H(...)O hydrogen bonds, and C—H(...)π inter­actions. There is also a C—H(...)O intra­molecular inter­action.

Related literature

For related literature, see: Jayabharathi et al. (2007 [triangle]); Thiruvalluvar et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1211-scheme1.jpg

Experimental

Crystal data

  • C26H28N2O3
  • M r = 416.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1211-efi1.jpg
  • a = 10.2472 (4) Å
  • b = 11.2723 (4) Å
  • c = 38.4188 (15) Å
  • V = 4437.7 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 160 (1) K
  • 0.25 × 0.13 × 0.10 mm

Data collection

  • Nonius KappaCCD area-detector diffractometer
  • Absorption correction: none
  • 36542 measured reflections
  • 3910 independent reflections
  • 2305 reflections with I > 2σ(I)
  • R int = 0.092

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.211
  • S = 1.08
  • 3910 reflections
  • 286 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.88 e Å−3
  • Δρmin = −0.75 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997 [triangle]); 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/S1600536808016449/wn2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016449/wn2266Isup2.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].

supplementary crystallographic information

Comment

In a wide research program toward new and efficient antimicrobial agents, a series of t3-benzyl-r2,c6-diarylpiperidin-4-ones have been synthesized and tested for their in vitro antibacterial and antifungal activities (Jayabharathi et al., 2007). 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 80.72 (15)°. The benzyl group at position 3 has an equatorial orientation. The oxime group at position 4 has a bisectional orientation. The phenyl ring of the benzyl group makes a dihedral angle of 64.71 (16)° with the benzene ring at C2, and 84.79 (17)° with the benzene ring at C6. Molecules are linked by intermolecular N1—H1···O6, O4—H4···N1 and C65—H65···O4 hydrogen bonds (Fig. 2). There are C12—H12B···π (-1 + x, y, z) interactions involving the phenyl ring at C13 and C16—H16A···π (1 - x, 1 - y, -z) interactions involving the benzene ring at C2. There is also a C5—H5A···O4 intramolecular interaction.

Experimental

The title compound was prepared according to the literature procedure (Jayabharathi et al., 2007). t3-Benzyl-r2,c6-bis(p-methoxyphenyl)piperidin-4-one (ca 0.05 mol, 20 g) and sodium acetate trihydrate (0.15 mol, 20.41 g) were dissolved in boiling ethanol and hydroxylamine hydrochloride (0.06 mol, 4.17 g) was added. The mixture was heated to 313 K and stirred for 3-4 h. It was allowed to stand overnight and then poured into crushed ice. The separated solid was filtered off and recrystallized from ethanol. The yield of the isolated pure product was 16 g (80%).

Refinement

The H atom bonded to N1 was located in a difference Fourier map and refined isotropically to an N—H bond length of 0.97 (3) 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 O—H = 0.84 Å; Uiso(H) = xUeq(carrier atom), where x = 1.5 for methyl and O, 1.2 for all others.

Figures

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.
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.

Crystal data

C26H28N2O3Dx = 1.247 Mg m3
Mr = 416.50Melting point: 460 K
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4402 reflections
a = 10.2472 (4) Åθ = 2.0–25.0º
b = 11.2723 (4) ŵ = 0.08 mm1
c = 38.4188 (15) ÅT = 160 (1) K
V = 4437.7 (3) Å3Tablet, colourless
Z = 80.25 × 0.13 × 0.10 mm
F000 = 1776

Data collection

Nonius KappaCCD area-detector diffractometer3910 independent reflections
Radiation source: Nonius FR590 sealed tube generator2305 reflections with I > 2σ(I)
Monochromator: horizontally mounted graphite crystalRint = 0.092
Detector resolution: 9 pixels mm-1θmax = 25.0º
T = 160(1) Kθmin = 3.1º
[var phi] and ω scans with κ offsetsh = −12→12
Absorption correction: nonek = −13→13
36542 measured reflectionsl = −45→45

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.070  w = 1/[σ2(Fo2) + (0.1121P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.211(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.88 e Å3
3910 reflectionsΔρmin = −0.75 e Å3
286 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (3)
Secondary atom site location: difference Fourier map

Special details

Experimental. Solvent used: Ethanol Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.618 (1) Frames collected: 629 Seconds exposure per frame: 35 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 57.3
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)

xyzUiso*/Ueq
O20.0668 (2)0.34156 (19)0.18566 (6)0.0420 (8)
O40.9150 (2)0.03452 (19)0.09433 (6)0.0386 (8)
O60.7048 (2)0.5478 (2)−0.05739 (5)0.0443 (9)
N10.5498 (3)0.2892 (2)0.08373 (6)0.0311 (9)
N40.8055 (2)0.0468 (2)0.11664 (6)0.0335 (9)
C20.5128 (3)0.1965 (3)0.10941 (8)0.0322 (11)
C30.6286 (3)0.1719 (3)0.13407 (8)0.0301 (10)
C40.7480 (3)0.1470 (3)0.11248 (8)0.0315 (11)
C50.7802 (3)0.2386 (3)0.08540 (8)0.0354 (11)
C60.6613 (3)0.2506 (3)0.06163 (8)0.0332 (11)
C12−0.0455 (3)0.2668 (3)0.18763 (10)0.0550 (16)
C130.5957 (3)0.0740 (3)0.16052 (8)0.0356 (11)
C160.8212 (3)0.6119 (3)−0.06432 (9)0.0533 (14)
C210.3912 (3)0.2353 (3)0.12845 (7)0.0292 (10)
C220.3900 (3)0.3387 (3)0.14823 (8)0.0339 (11)
C230.2808 (3)0.3721 (3)0.16668 (8)0.0355 (11)
C240.1683 (3)0.3020 (3)0.16566 (8)0.0338 (11)
C250.1667 (3)0.1996 (3)0.14565 (8)0.0367 (12)
C260.2785 (3)0.1679 (3)0.12733 (8)0.0357 (11)
C310.6756 (3)0.0789 (3)0.19370 (8)0.0341 (11)
C320.6473 (3)0.1655 (3)0.21837 (8)0.0433 (12)
C330.7156 (4)0.1699 (4)0.24939 (10)0.0553 (16)
C340.8112 (4)0.0882 (4)0.25647 (10)0.0570 (16)
C350.8412 (4)0.0025 (3)0.23256 (10)0.0537 (14)
C360.7748 (3)−0.0020 (3)0.20113 (9)0.0433 (12)
C610.6775 (3)0.3337 (3)0.03083 (8)0.0323 (11)
C620.7835 (3)0.4086 (3)0.02694 (8)0.0413 (12)
C630.7969 (3)0.4812 (3)−0.00223 (8)0.0413 (12)
C640.7021 (3)0.4801 (3)−0.02775 (8)0.0350 (11)
C650.5951 (3)0.4067 (3)−0.02416 (8)0.0420 (12)
C660.5834 (3)0.3338 (3)0.00450 (8)0.0377 (12)
H10.473 (3)0.304 (2)0.0698 (8)0.030 (8)*
H20.492580.121790.096440.0385*
H30.645510.246320.147490.0362*
H40.94084−0.036200.094640.0578*
H5A0.857380.213560.071750.0422*
H5B0.799980.315600.096630.0422*
H60.640310.170030.052310.0397*
H12A−0.111350.303920.202580.0825*
H12B−0.020610.189720.197410.0825*
H12C−0.081650.255350.164250.0825*
H13A0.502110.080100.166670.0426*
H13B0.60941−0.004100.149340.0426*
H16A0.811340.65636−0.086070.0794*
H16B0.894310.55628−0.066500.0794*
H16C0.838400.66712−0.045170.0794*
H220.465830.387150.149030.0407*
H230.281820.442910.180100.0423*
H250.090430.151820.144480.0437*
H260.277380.097810.113620.0430*
H320.580530.221970.213880.0523*
H330.696110.230010.265930.0666*
H340.856560.091140.278010.0684*
H350.90752−0.054010.237490.0643*
H360.79716−0.060790.184450.0518*
H620.848540.410660.044540.0494*
H630.870980.53122−0.004530.0494*
H650.529220.40631−0.041550.0504*
H660.509950.282790.006390.0456*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O20.0306 (14)0.0431 (15)0.0524 (15)0.0035 (11)0.0109 (11)0.0070 (11)
O40.0371 (14)0.0361 (14)0.0425 (14)0.0086 (11)0.0105 (11)0.0036 (11)
O60.0489 (16)0.0493 (15)0.0346 (14)−0.0048 (12)−0.0022 (11)0.0123 (11)
N10.0307 (16)0.0346 (16)0.0281 (15)0.0018 (13)0.0001 (13)0.0027 (12)
N40.0346 (16)0.0354 (16)0.0305 (15)0.0030 (13)0.0040 (12)−0.0005 (12)
C20.037 (2)0.0283 (18)0.0314 (18)−0.0022 (15)0.0047 (15)0.0008 (14)
C30.0315 (18)0.0288 (18)0.0301 (17)−0.0003 (14)0.0031 (15)0.0009 (14)
C40.0330 (19)0.033 (2)0.0284 (18)0.0013 (16)0.0000 (14)−0.0007 (15)
C50.033 (2)0.039 (2)0.0341 (19)0.0052 (16)0.0058 (15)0.0046 (16)
C60.039 (2)0.0301 (18)0.0306 (18)0.0007 (15)0.0037 (16)−0.0001 (14)
C120.036 (2)0.060 (3)0.069 (3)−0.002 (2)0.0122 (19)0.013 (2)
C130.036 (2)0.0353 (19)0.0354 (18)0.0010 (15)0.0039 (15)0.0018 (16)
C160.060 (3)0.058 (2)0.042 (2)−0.006 (2)0.0018 (19)0.0152 (19)
C210.0304 (19)0.0284 (18)0.0288 (17)−0.0007 (15)0.0001 (14)0.0028 (14)
C220.0282 (19)0.0326 (19)0.041 (2)−0.0019 (15)0.0017 (16)0.0013 (16)
C230.038 (2)0.0306 (18)0.038 (2)0.0013 (17)0.0023 (16)0.0003 (15)
C240.030 (2)0.036 (2)0.0353 (19)0.0026 (16)0.0013 (15)0.0091 (16)
C250.033 (2)0.034 (2)0.043 (2)−0.0048 (16)0.0005 (16)0.0077 (16)
C260.040 (2)0.0319 (19)0.0353 (19)−0.0023 (16)−0.0020 (16)0.0001 (15)
C310.0357 (19)0.037 (2)0.0297 (18)−0.0054 (17)0.0040 (15)0.0056 (16)
C320.042 (2)0.053 (2)0.035 (2)−0.0030 (18)0.0065 (17)−0.0007 (18)
C330.059 (3)0.071 (3)0.036 (2)−0.017 (2)0.009 (2)−0.007 (2)
C340.058 (3)0.071 (3)0.042 (2)−0.025 (2)−0.010 (2)0.014 (2)
C350.050 (2)0.050 (2)0.061 (3)−0.005 (2)−0.014 (2)0.021 (2)
C360.047 (2)0.039 (2)0.044 (2)−0.0003 (18)0.0009 (18)0.0073 (17)
C610.0350 (19)0.0334 (19)0.0286 (18)0.0013 (16)0.0039 (15)−0.0022 (14)
C620.041 (2)0.049 (2)0.034 (2)−0.0036 (18)−0.0036 (16)0.0096 (17)
C630.042 (2)0.044 (2)0.038 (2)−0.0094 (17)0.0002 (17)0.0078 (17)
C640.042 (2)0.036 (2)0.0270 (19)0.0054 (16)0.0016 (16)0.0046 (15)
C650.045 (2)0.046 (2)0.035 (2)−0.0027 (18)−0.0090 (17)0.0028 (17)
C660.041 (2)0.036 (2)0.036 (2)−0.0047 (16)−0.0010 (16)0.0016 (16)

Geometric parameters (Å, °)

O2—C121.428 (4)C61—C621.384 (5)
O2—C241.368 (4)C62—C631.395 (5)
O4—N41.419 (3)C63—C641.380 (4)
O6—C161.420 (4)C64—C651.381 (5)
O6—C641.371 (4)C65—C661.379 (5)
O4—H40.8400C2—H21.0000
N1—C61.489 (4)C3—H31.0000
N1—C21.486 (4)C5—H5A0.9900
N4—C41.284 (4)C5—H5B0.9900
N1—H10.97 (3)C6—H61.0000
C2—C31.544 (4)C12—H12A0.9800
C2—C211.510 (4)C12—H12B0.9800
C3—C131.538 (5)C12—H12C0.9800
C3—C41.505 (4)C13—H13A0.9900
C4—C51.503 (5)C13—H13B0.9900
C5—C61.529 (4)C16—H16A0.9800
C6—C611.518 (5)C16—H16B0.9800
C13—C311.516 (4)C16—H16C0.9800
C21—C221.392 (5)C22—H220.9500
C21—C261.383 (4)C23—H230.9500
C22—C231.377 (4)C25—H250.9500
C23—C241.398 (4)C26—H260.9500
C24—C251.387 (5)C32—H320.9500
C25—C261.391 (4)C33—H330.9500
C31—C361.395 (5)C34—H340.9500
C31—C321.391 (5)C35—H350.9500
C32—C331.383 (5)C36—H360.9500
C33—C341.372 (6)C62—H620.9500
C34—C351.368 (6)C63—H630.9500
C35—C361.387 (5)C65—H650.9500
C61—C661.398 (4)C66—H660.9500
O2···C13i3.251 (4)H3···C322.8700
O4···N1ii2.818 (3)H3···H222.4300
O4···C65iii3.334 (4)H4···N1ii2.0100
O2···H13Bi2.8700H4···C6ii2.9100
O2···H33iv2.6100H4···C22ii3.0400
O2···H13Ai2.8700H4···H1ii2.2200
O4···H65iii2.4300H4···H22ii2.4600
O4···H5A2.2700H5A···O42.2700
O6···H26iii2.8100H5A···C622.8900
O6···H1v2.52 (3)H5A···H622.4600
N1···O4vi2.818 (3)H5A···H65iii2.5000
N4···C313.266 (4)H5B···C622.8800
N4···C363.307 (4)H5B···H622.3200
N1···H4vi2.0100H5B···N4vi2.9200
N1···H222.8700H6···H22.3400
N4···H13B2.4400H6···H662.5500
N4···H362.8700H6···C63ii3.0600
N4···H5Bii2.9200H12A···C32vii2.9900
C12···C36vii3.583 (5)H12A···C33vii2.9400
C12···C31vii3.565 (5)H12A···C36i2.7600
C12···C32vii3.551 (4)H12A···H36i2.5400
C12···C36i3.547 (5)H12B···C252.7700
C12···C33vii3.580 (5)H12B···C34vii3.0700
C13···O2viii3.251 (4)H12B···C35vii2.8800
C31···C12ix3.565 (5)H12B···C36vii3.0100
C31···N43.266 (4)H12B···H252.3700
C32···C12ix3.551 (4)H12C···C4vii2.9100
C33···C12ix3.580 (5)H12C···C252.7200
C36···C12ix3.583 (5)H12C···H252.2500
C36···C12viii3.547 (5)H13A···C212.5500
C36···N43.307 (4)H13A···C262.9200
C65···O4x3.334 (4)H13A···H322.5500
C65···C66v3.532 (5)H13A···H34iv2.6000
C65···C65v3.416 (5)H13A···O2viii2.8700
C66···C65v3.532 (5)H13B···N42.4400
C3···H223.0000H13B···H362.4400
C4···H12Cix2.9100H13B···O2viii2.8700
C5···H622.5900H13B···C12viii3.0400
C6···H4vi2.9100H16A···C21v2.9100
C12···H33iv3.0800H16A···C25v2.8200
C12···H13Bi3.0400H16A···C26v2.7000
C12···H252.5200H16B···C632.7900
C16···H26iii3.0600H16B···H632.4100
C16···H632.5200H16B···H2iii2.5200
C21···H13A2.5500H16C···C632.7000
C21···H16Av2.9100H16C···H632.2100
C22···H32.8200H16C···C65vi2.9000
C22···H4vi3.0400H16C···C66vi2.8000
C24···H33iv2.7700H22···N12.8700
C25···H16Av2.8200H22···C33.0000
C25···H12C2.7200H22···H32.4300
C25···H12B2.7700H22···H4vi2.4600
C26···H13A2.9200H23···C34xii3.0900
C26···H16Av2.7000H25···C122.5200
C32···H34iv3.1000H25···H12B2.3700
C32···H32.8700H25···H12C2.2500
C32···H12Aix2.9900H26···H22.3200
C33···H12Aix2.9400H26···O6x2.8100
C34···H12Bix3.0700H26···C16x3.0600
C34···H23xi3.0900H32···H13A2.5500
C35···H12Bix2.8800H33···O2xiii2.6100
C36···H12Bix3.0100H33···C12xiii3.0800
C36···H12Aviii2.7600H33···C24xiii2.7700
C62···H5B2.8800H34···C32xiii3.1000
C62···H5A2.8900H34···H13Axiii2.6000
C63···H16B2.7900H36···N42.8700
C63···H6vi3.0600H36···H13B2.4400
C63···H16C2.7000H36···H12Aviii2.5400
C65···H16Cii2.9000H62···C52.5900
C66···H12.77 (3)H62···H5A2.4600
C66···H16Cii2.8000H62···H5B2.3200
H1···C662.77 (3)H63···C162.5200
H1···H662.4800H63···H16B2.4100
H1···O6v2.52 (3)H63···H16C2.2100
H1···H4vi2.2200H65···O4x2.4300
H2···H62.3400H65···H5Ax2.5000
H2···H262.3200H66···H12.4800
H2···H16Bx2.5200H66···H62.5500
H3···C222.8200
C12—O2—C24116.8 (2)C4—C3—H3107.00
C16—O6—C64117.1 (2)C13—C3—H3107.00
N4—O4—H4109.00C4—C5—H5A110.00
C2—N1—C6111.7 (2)C4—C5—H5B110.00
O4—N4—C4111.9 (2)C6—C5—H5A110.00
C6—N1—H1111.1 (18)C6—C5—H5B110.00
C2—N1—H1106.3 (17)H5A—C5—H5B108.00
N1—C2—C3109.7 (3)N1—C6—H6108.00
N1—C2—C21109.2 (3)C5—C6—H6108.00
C3—C2—C21112.9 (2)C61—C6—H6108.00
C2—C3—C4108.7 (2)O2—C12—H12A110.00
C2—C3—C13111.5 (3)O2—C12—H12B109.00
C4—C3—C13114.1 (3)O2—C12—H12C109.00
N4—C4—C5126.2 (3)H12A—C12—H12B109.00
N4—C4—C3118.0 (3)H12A—C12—H12C109.00
C3—C4—C5115.6 (3)H12B—C12—H12C109.00
C4—C5—C6107.4 (3)C3—C13—H13A109.00
N1—C6—C5107.3 (2)C3—C13—H13B109.00
C5—C6—C61115.7 (3)C31—C13—H13A109.00
N1—C6—C61110.4 (3)C31—C13—H13B109.00
C3—C13—C31114.3 (3)H13A—C13—H13B108.00
C22—C21—C26118.0 (3)O6—C16—H16A109.00
C2—C21—C26121.0 (3)O6—C16—H16B109.00
C2—C21—C22121.0 (3)O6—C16—H16C109.00
C21—C22—C23121.2 (3)H16A—C16—H16B109.00
C22—C23—C24120.1 (3)H16A—C16—H16C110.00
O2—C24—C23115.3 (3)H16B—C16—H16C109.00
O2—C24—C25125.0 (3)C21—C22—H22119.00
C23—C24—C25119.7 (3)C23—C22—H22119.00
C24—C25—C26119.0 (3)C22—C23—H23120.00
C21—C26—C25122.1 (3)C24—C23—H23120.00
C13—C31—C32119.1 (3)C24—C25—H25121.00
C13—C31—C36122.8 (3)C26—C25—H25121.00
C32—C31—C36118.1 (3)C21—C26—H26119.00
C31—C32—C33120.5 (3)C25—C26—H26119.00
C32—C33—C34120.5 (4)C31—C32—H32120.00
C33—C34—C35120.1 (4)C33—C32—H32120.00
C34—C35—C36120.0 (3)C32—C33—H33120.00
C31—C36—C35120.8 (3)C34—C33—H33120.00
C6—C61—C62123.1 (3)C33—C34—H34120.00
C6—C61—C66119.3 (3)C35—C34—H34120.00
C62—C61—C66117.6 (3)C34—C35—H35120.00
C61—C62—C63121.5 (3)C36—C35—H35120.00
C62—C63—C64119.8 (3)C31—C36—H36120.00
O6—C64—C65115.6 (3)C35—C36—H36120.00
O6—C64—C63124.8 (3)C61—C62—H62119.00
C63—C64—C65119.6 (3)C63—C62—H62119.00
C64—C65—C66120.4 (3)C62—C63—H63120.00
C61—C66—C65121.2 (3)C64—C63—H63120.00
N1—C2—H2108.00C64—C65—H65120.00
C3—C2—H2108.00C66—C65—H65120.00
C21—C2—H2108.00C61—C66—H66119.00
C2—C3—H3107.00C65—C66—H66119.00
C12—O2—C24—C23−174.7 (3)C5—C6—C61—C66168.6 (3)
C12—O2—C24—C254.3 (4)C3—C13—C31—C3274.9 (4)
C16—O6—C64—C638.4 (4)C3—C13—C31—C36−106.8 (4)
C16—O6—C64—C65−171.6 (3)C2—C21—C22—C23−177.6 (3)
C6—N1—C2—C361.5 (3)C26—C21—C22—C231.2 (5)
C6—N1—C2—C21−174.2 (2)C2—C21—C26—C25177.7 (3)
C2—N1—C6—C5−65.7 (3)C22—C21—C26—C25−1.0 (5)
C2—N1—C6—C61167.5 (2)C21—C22—C23—C24−0.2 (5)
O4—N4—C4—C3179.1 (2)C22—C23—C24—O2178.3 (3)
O4—N4—C4—C55.6 (4)C22—C23—C24—C25−0.8 (5)
N1—C2—C3—C4−51.9 (3)O2—C24—C25—C26−178.1 (3)
N1—C2—C3—C13−178.5 (2)C23—C24—C25—C260.9 (5)
C21—C2—C3—C4−173.9 (3)C24—C25—C26—C210.0 (5)
C21—C2—C3—C1359.5 (4)C13—C31—C32—C33177.9 (3)
N1—C2—C21—C22−61.0 (4)C36—C31—C32—C33−0.4 (5)
N1—C2—C21—C26120.4 (3)C13—C31—C36—C35−176.9 (3)
C3—C2—C21—C2261.4 (4)C32—C31—C36—C351.4 (5)
C3—C2—C21—C26−117.3 (3)C31—C32—C33—C34−0.7 (6)
C2—C3—C4—N4−121.5 (3)C32—C33—C34—C351.0 (6)
C2—C3—C4—C552.7 (4)C33—C34—C35—C36−0.1 (6)
C13—C3—C4—N43.6 (4)C34—C35—C36—C31−1.1 (5)
C13—C3—C4—C5177.8 (3)C6—C61—C62—C63178.1 (3)
C2—C3—C13—C31−155.9 (3)C66—C61—C62—C63−0.4 (5)
C4—C3—C13—C3180.5 (3)C6—C61—C66—C65−179.1 (3)
N4—C4—C5—C6116.3 (3)C62—C61—C66—C65−0.6 (5)
C3—C4—C5—C6−57.3 (3)C61—C62—C63—C640.8 (5)
C4—C5—C6—N160.3 (3)C62—C63—C64—O6179.8 (3)
C4—C5—C6—C61−176.1 (3)C62—C63—C64—C65−0.2 (5)
N1—C6—C61—C62112.1 (3)O6—C64—C65—C66179.3 (3)
N1—C6—C61—C66−69.4 (4)C63—C64—C65—C66−0.8 (5)
C5—C6—C61—C62−9.9 (5)C64—C65—C66—C611.2 (5)

Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+3/2, y−1/2, z; (iii) x+1/2, −y+1/2, −z; (iv) x−1/2, y, −z+1/2; (v) −x+1, −y+1, −z; (vi) −x+3/2, y+1/2, z; (vii) x−1, y, z; (viii) −x+1/2, y−1/2, z; (ix) x+1, y, z; (x) x−1/2, −y+1/2, −z; (xi) −x+1, y−1/2, −z+1/2; (xii) −x+1, y+1/2, −z+1/2; (xiii) x+1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O6v0.97 (3)2.52 (3)3.348 (3)144 (2)
O4—H4···N1ii0.842.012.818 (3)160
C5—H5A···O40.992.272.705 (4)105
C65—H65···O4x0.952.433.334 (4)158
C12—H12B···Cg1vii0.982.893.314 (4)107
C16—H16A···Cg2v0.982.653.598 (4)162

Symmetry codes: (v) −x+1, −y+1, −z; (ii) −x+3/2, y−1/2, z; (x) x−1/2, −y+1/2, −z; (vii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2266).

References

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  • 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. New York: Academic Press.
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