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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1181.
Published online 2008 June 7. doi:  10.1107/S1600536808015717
PMCID: PMC2961717

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

Abstract

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 [triangle]); Thiruvalluvar et al. (2007 [triangle]); Noller & Baliah (1948 [triangle]).

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Object name is e-64-o1181-scheme1.jpg

Experimental

Crystal data

  • C26H27NO3
  • M r = 401.49
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1181-efi1.jpg
  • 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)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 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

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/S1600536808015717/wn2265sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015717/wn2265Isup2.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

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.

Experimental

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

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.

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

C26H27NO3Z = 2
Mr = 401.49F000 = 428
Triclinic, P1Dx = 1.285 Mg m3
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 = 2.0–27.5º
α = 71.629 (2)ºµ = 0.08 mm1
β = 79.928 (2)ºT = 160 (1) K
γ = 82.526 (2)ºPrism, colourless
V = 1038.04 (7) Å30.30 × 0.18 × 0.13 mm

Data collection

Nonius KappaCCD area-detector diffractometer4740 independent reflections
Radiation source: Nonius FR590 sealed tube generator3325 reflections with I > 2σ(I)
Monochromator: horizontally mounted graphite crystalRint = 0.052
Detector resolution: 9 pixels mm-1θmax = 27.5º
T = 160(1) Kθmin = 3.0º
[var phi] and ω scans with κ offsetsh = −7→7
Absorption correction: nonek = −17→17
25390 measured reflectionsl = −17→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.177  w = 1/[σ2(Fo2) + (0.1039P)2 + 0.0262P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
4740 reflectionsΔρmax = 0.28 e Å3
275 parametersΔρmin = −0.32 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

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)

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, °)

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, °)

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; (xii) x+1, y, z; (v) −x+2, −y+1, −z; (ix) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2265).

References

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