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In the title compound, C21H31NO, the cyclo­butane ring is puckered, with a dihedral angle of 25.74 (6)°. The mesit­yl and 2-N-piperidino-1-oxoeth­yl groups are in cis positions. The piperidine fragment adopts a chair conformation. Inter­molecular C—H...O inter­actions involving the piperidine CH group and the keto O atom lead to the formation of dimers, and inter­molecular C—H...π inter­actions involving the cyclo­butane CH group and the benzene ring are responsible for the formation of a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501487X/ob6518sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501487X/ob6518Isup2.hkl
Contains datablock I

CCDC reference: 274606

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.112
  • Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. O1 .. 2.65 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H31 N O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

1-(3-Mesityl-3-methylcyclobutyl)-2-(piperidin-1-yl)ethanone top
Crystal data top
C21H31NOF(000) = 688
Mr = 313.47Dx = 1.146 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 30333 reflections
a = 13.3063 (7) Åθ = 2.1–28.0°
b = 9.8112 (3) ŵ = 0.07 mm1
c = 13.9186 (7) ÅT = 100 K
β = 91.702 (4)°Prism, light yellow
V = 1816.28 (14) Å30.46 × 0.32 × 0.20 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
4334 independent reflections
Radiation source: sealed X-ray tube3647 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.090
Detector resolution: 6.67 pixels mm-1θmax = 28.0°, θmin = 2.1°
ω scansh = 1717
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)
k = 1212
Tmin = 0.666, Tmax = 0.948l = 1818
30598 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0538P)2 + 0.587P]
where P 97 = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4334 reflectionsΔρmax = 0.34 e Å3
212 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0109 (17)
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
O10.06810 (7)0.19550 (9)0.58883 (6)0.0256 (2)
N10.16428 (7)0.07644 (10)0.66170 (7)0.0191 (2)
C10.17716 (9)0.01687 (12)0.56520 (8)0.0199 (2)
H1A0.11220.01050.54200.024*
H1B0.20510.08480.52140.024*
C20.24637 (9)0.10590 (13)0.56677 (9)0.0249 (3)
H2A0.21680.17600.60780.030*
H2B0.25460.14290.50240.030*
C30.34829 (10)0.06537 (16)0.60404 (11)0.0335 (3)
H3A0.38950.14600.61150.040*
H3B0.38220.00550.55810.040*
C40.33534 (11)0.00713 (16)0.70044 (10)0.0333 (3)
H4A0.40000.04120.72020.040*
H4B0.31100.05720.74870.040*
C50.26168 (9)0.12509 (13)0.69430 (9)0.0255 (3)
H5A0.28830.19300.64980.031*
H5B0.25300.16750.75700.031*
C60.05195 (9)0.02263 (11)0.70807 (8)0.0183 (2)
H60.02990.03450.77410.022*
C70.03092 (9)0.12561 (11)0.67320 (8)0.0184 (2)
H7A0.01960.13340.60420.022*
H7B0.02180.17120.70760.022*
C80.13952 (8)0.16661 (11)0.70825 (8)0.0170 (2)
C90.16442 (8)0.01080 (11)0.70776 (8)0.0185 (2)
H9A0.20120.01980.76500.022*
H9B0.19720.01920.65010.022*
C100.09240 (9)0.18804 (12)0.65933 (9)0.0217 (2)
H10A0.09510.23890.71900.026*
H10B0.11130.24930.60720.026*
C110.01471 (9)0.13877 (11)0.64581 (8)0.0189 (2)
C120.14055 (10)0.22104 (12)0.81163 (8)0.0227 (2)
H12A0.10280.16080.85120.034*
H12B0.20870.22620.83610.034*
H12C0.11090.31020.81220.034*
C130.19875 (8)0.25923 (11)0.64257 (7)0.0164 (2)
C140.15210 (8)0.37112 (11)0.59552 (8)0.0179 (2)
C150.20585 (9)0.45011 (12)0.53145 (8)0.0207 (2)
H150.17390.52330.50110.025*
C160.30558 (9)0.42308 (12)0.51144 (8)0.0214 (2)
C170.35248 (9)0.31813 (12)0.56246 (8)0.0201 (2)
H170.42000.30050.55220.024*
C180.30209 (8)0.23817 (11)0.62851 (8)0.0180 (2)
C190.04484 (9)0.41305 (12)0.61224 (9)0.0218 (2)
H19A0.00020.36010.57170.033*
H19B0.02950.39770.67830.033*
H19C0.03660.50800.59740.033*
C200.36053 (11)0.50581 (15)0.43835 (9)0.0302 (3)
H20A0.33760.48020.37480.045*
H20B0.34760.60090.44830.045*
H20C0.43140.48890.44540.045*
C210.36385 (9)0.13319 (12)0.68359 (9)0.0235 (3)
H21A0.43350.15850.68340.035*
H21B0.34200.12880.74860.035*
H21C0.35520.04560.65370.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0289 (5)0.0218 (4)0.0265 (4)0.0021 (4)0.0051 (3)0.0039 (3)
N10.0210 (5)0.0184 (5)0.0179 (4)0.0020 (4)0.0022 (3)0.0004 (3)
C10.0215 (5)0.0223 (6)0.0160 (5)0.0008 (4)0.0012 (4)0.0015 (4)
C20.0255 (6)0.0273 (6)0.0221 (5)0.0037 (5)0.0026 (4)0.0024 (5)
C30.0241 (6)0.0399 (8)0.0367 (7)0.0075 (6)0.0059 (5)0.0048 (6)
C40.0290 (7)0.0381 (7)0.0336 (7)0.0042 (6)0.0144 (5)0.0051 (6)
C50.0251 (6)0.0253 (6)0.0265 (6)0.0045 (5)0.0062 (5)0.0019 (5)
C60.0211 (5)0.0169 (5)0.0169 (5)0.0015 (4)0.0009 (4)0.0009 (4)
C70.0188 (5)0.0160 (5)0.0205 (5)0.0008 (4)0.0000 (4)0.0003 (4)
C80.0191 (5)0.0157 (5)0.0162 (5)0.0003 (4)0.0007 (4)0.0006 (4)
C90.0200 (5)0.0159 (5)0.0197 (5)0.0002 (4)0.0012 (4)0.0020 (4)
C100.0235 (6)0.0161 (5)0.0255 (6)0.0035 (4)0.0003 (4)0.0000 (4)
C110.0236 (6)0.0151 (5)0.0180 (5)0.0005 (4)0.0005 (4)0.0029 (4)
C120.0291 (6)0.0216 (6)0.0174 (5)0.0037 (5)0.0008 (4)0.0010 (4)
C130.0189 (5)0.0152 (5)0.0150 (5)0.0018 (4)0.0018 (4)0.0018 (4)
C140.0206 (5)0.0162 (5)0.0166 (5)0.0010 (4)0.0023 (4)0.0017 (4)
C150.0248 (6)0.0177 (5)0.0193 (5)0.0015 (4)0.0038 (4)0.0028 (4)
C160.0255 (6)0.0214 (6)0.0172 (5)0.0058 (5)0.0009 (4)0.0001 (4)
C170.0184 (5)0.0208 (5)0.0212 (5)0.0021 (4)0.0007 (4)0.0032 (4)
C180.0198 (5)0.0160 (5)0.0180 (5)0.0007 (4)0.0019 (4)0.0023 (4)
C190.0218 (6)0.0183 (5)0.0251 (6)0.0024 (4)0.0010 (4)0.0020 (4)
C200.0314 (7)0.0333 (7)0.0260 (6)0.0076 (6)0.0017 (5)0.0079 (5)
C210.0186 (5)0.0212 (6)0.0306 (6)0.0002 (4)0.0028 (4)0.0032 (5)
Geometric parameters (Å, º) top
O1—C111.2154 (14)C9—H9A0.9700
N1—C101.4549 (15)C9—H9B0.9700
N1—C51.4657 (15)C10—C111.5219 (16)
N1—C11.4702 (14)C10—H10A0.9700
C1—C21.5168 (17)C10—H10B0.9700
C1—H1A0.9700C12—H12A0.9600
C1—H1B0.9700C12—H12B0.9600
C2—C31.5192 (18)C12—H12C0.9600
C2—H2A0.9700C13—C181.4099 (15)
C2—H2B0.9700C13—C141.4125 (15)
C3—C41.524 (2)C14—C151.3947 (16)
C3—H3A0.9700C14—C191.5100 (16)
C3—H3B0.9700C15—C161.3896 (17)
C4—C51.5207 (19)C15—H150.9300
C4—H4A0.9700C16—C171.3883 (17)
C4—H4B0.9700C16—C201.5075 (16)
C5—H5A0.9700C17—C181.3953 (16)
C5—H5B0.9700C17—H170.9300
C6—C111.5064 (15)C18—C211.5121 (16)
C6—C91.5322 (15)C19—H19A0.9600
C6—C71.5560 (15)C19—H19B0.9600
C6—H60.9800C19—H19C0.9600
C7—C81.5639 (15)C20—H20A0.9600
C7—H7A0.9700C20—H20B0.9600
C7—H7B0.9700C20—H20C0.9600
C8—C131.5250 (15)C21—H21A0.9600
C8—C121.5344 (15)C21—H21B0.9600
C8—C91.5642 (15)C21—H21C0.9600
C10—N1—C5110.48 (9)C6—C9—H9B113.6
C10—N1—C1109.71 (9)C8—C9—H9B113.6
C5—N1—C1109.40 (9)H9A—C9—H9B110.9
N1—C1—C2110.90 (9)N1—C10—C11112.49 (9)
N1—C1—H1A109.5N1—C10—H10A109.1
C2—C1—H1A109.5C11—C10—H10A109.1
N1—C1—H1B109.5N1—C10—H10B109.1
C2—C1—H1B109.5C11—C10—H10B109.1
H1A—C1—H1B108.0H10A—C10—H10B107.8
C1—C2—C3110.22 (11)O1—C11—C6122.22 (11)
C1—C2—H2A109.6O1—C11—C10120.19 (10)
C3—C2—H2A109.6C6—C11—C10117.54 (10)
C1—C2—H2B109.6C8—C12—H12A109.5
C3—C2—H2B109.6C8—C12—H12B109.5
H2A—C2—H2B108.1H12A—C12—H12B109.5
C2—C3—C4110.13 (11)C8—C12—H12C109.5
C2—C3—H3A109.6H12A—C12—H12C109.5
C4—C3—H3A109.6H12B—C12—H12C109.5
C2—C3—H3B109.6C18—C13—C14117.81 (10)
C4—C3—H3B109.6C18—C13—C8121.29 (10)
H3A—C3—H3B108.1C14—C13—C8120.88 (10)
C5—C4—C3111.22 (11)C15—C14—C13120.11 (10)
C5—C4—H4A109.4C15—C14—C19116.88 (10)
C3—C4—H4A109.4C13—C14—C19123.00 (10)
C5—C4—H4B109.4C16—C15—C14122.21 (11)
C3—C4—H4B109.4C16—C15—H15118.9
H4A—C4—H4B108.0C14—C15—H15118.9
N1—C5—C4110.30 (10)C17—C16—C15117.16 (11)
N1—C5—H5A109.6C17—C16—C20121.66 (11)
C4—C5—H5A109.6C15—C16—C20121.18 (11)
N1—C5—H5B109.6C16—C17—C18122.45 (11)
C4—C5—H5B109.6C16—C17—H17118.8
H5A—C5—H5B108.1C18—C17—H17118.8
C11—C6—C9117.71 (10)C17—C18—C13119.92 (10)
C11—C6—C7118.34 (9)C17—C18—C21116.90 (10)
C9—C6—C788.03 (8)C13—C18—C21123.17 (10)
C11—C6—H6110.3C14—C19—H19A109.5
C9—C6—H6110.3C14—C19—H19B109.5
C7—C6—H6110.3H19A—C19—H19B109.5
C6—C7—C889.27 (8)C14—C19—H19C109.5
C6—C7—H7A113.8H19A—C19—H19C109.5
C8—C7—H7A113.8H19B—C19—H19C109.5
C6—C7—H7B113.8C16—C20—H20A109.5
C8—C7—H7B113.8C16—C20—H20B109.5
H7A—C7—H7B111.0H20A—C20—H20B109.5
C13—C8—C12111.37 (9)C16—C20—H20C109.5
C13—C8—C7117.09 (9)H20A—C20—H20C109.5
C12—C8—C7111.38 (9)H20B—C20—H20C109.5
C13—C8—C9117.80 (9)C18—C21—H21A109.5
C12—C8—C9110.38 (9)C18—C21—H21B109.5
C7—C8—C986.63 (8)H21A—C21—H21B109.5
C6—C9—C890.13 (8)C18—C21—H21C109.5
C6—C9—H9A113.6H21A—C21—H21C109.5
C8—C9—H9A113.6H21B—C21—H21C109.5
C10—N1—C1—C2176.18 (9)N1—C10—C11—O1134.98 (11)
C5—N1—C1—C262.47 (12)N1—C10—C11—C647.46 (13)
N1—C1—C2—C358.48 (13)C12—C8—C13—C1890.74 (12)
C1—C2—C3—C453.05 (15)C7—C8—C13—C18139.49 (10)
C2—C3—C4—C552.90 (16)C9—C8—C13—C1838.24 (14)
C10—N1—C5—C4177.78 (10)C12—C8—C13—C1487.76 (12)
C1—N1—C5—C461.34 (13)C7—C8—C13—C1442.01 (14)
C3—C4—C5—N157.30 (15)C9—C8—C13—C14143.25 (10)
C11—C6—C7—C8139.09 (10)C18—C13—C14—C155.11 (15)
C9—C6—C7—C818.42 (8)C8—C13—C14—C15176.33 (10)
C6—C7—C8—C13137.71 (10)C18—C13—C14—C19173.77 (10)
C6—C7—C8—C1292.53 (10)C8—C13—C14—C194.79 (16)
C6—C7—C8—C918.06 (8)C13—C14—C15—C160.06 (17)
C11—C6—C9—C8139.64 (10)C19—C14—C15—C16178.89 (10)
C7—C6—C9—C818.42 (8)C14—C15—C16—C173.79 (17)
C13—C8—C9—C6137.33 (9)C14—C15—C16—C20177.03 (11)
C12—C8—C9—C693.22 (10)C15—C16—C17—C182.55 (17)
C7—C8—C9—C618.34 (8)C20—C16—C17—C18178.27 (11)
C5—N1—C10—C11168.37 (9)C16—C17—C18—C132.52 (17)
C1—N1—C10—C1170.94 (12)C16—C17—C18—C21176.27 (11)
C9—C6—C11—O18.08 (16)C14—C13—C18—C176.29 (15)
C7—C6—C11—O195.75 (14)C8—C13—C18—C17175.16 (10)
C9—C6—C11—C10169.43 (9)C14—C13—C18—C21172.43 (10)
C7—C6—C11—C1086.74 (12)C8—C13—C18—C216.12 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O10.972.572.8903 (14)100
C1—H1A···O1i0.972.653.3508 (15)130
C9—H9A···Cg1ii0.972.613.5435 (14)160
Symmetry codes: (i) x, y, z+1; (ii) x+3/2, y1/2, z+1/2.
 

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