In the title compound, C
21H
31NO, 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
CCDC reference: 274606
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
C21H31NO | F(000) = 688 |
Mr = 313.47 | Dx = 1.146 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 30333 reflections |
a = 13.3063 (7) Å | θ = 2.1–28.0° |
b = 9.8112 (3) Å | µ = 0.07 mm−1 |
c = 13.9186 (7) Å | T = 100 K |
β = 91.702 (4)° | Prism, light yellow |
V = 1816.28 (14) Å3 | 0.46 × 0.32 × 0.20 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 4334 independent reflections |
Radiation source: sealed X-ray tube | 3647 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.090 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.0°, θmin = 2.1° |
ω scans | h = −17→17 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −12→12 |
Tmin = 0.666, Tmax = 0.948 | l = −18→18 |
30598 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-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 reflections | Δρmax = 0.34 e Å−3 |
212 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.06810 (7) | 0.19550 (9) | 0.58883 (6) | 0.0256 (2) | |
N1 | −0.16428 (7) | 0.07644 (10) | 0.66170 (7) | 0.0191 (2) | |
C1 | −0.17716 (9) | 0.01687 (12) | 0.56520 (8) | 0.0199 (2) | |
H1A | −0.1122 | −0.0105 | 0.5420 | 0.024* | |
H1B | −0.2051 | 0.0848 | 0.5214 | 0.024* | |
C2 | −0.24637 (9) | −0.10590 (13) | 0.56677 (9) | 0.0249 (3) | |
H2A | −0.2168 | −0.1760 | 0.6078 | 0.030* | |
H2B | −0.2546 | −0.1429 | 0.5024 | 0.030* | |
C3 | −0.34829 (10) | −0.06537 (16) | 0.60404 (11) | 0.0335 (3) | |
H3A | −0.3895 | −0.1460 | 0.6115 | 0.040* | |
H3B | −0.3822 | −0.0055 | 0.5581 | 0.040* | |
C4 | −0.33534 (11) | 0.00713 (16) | 0.70044 (10) | 0.0333 (3) | |
H4A | −0.4000 | 0.0412 | 0.7202 | 0.040* | |
H4B | −0.3110 | −0.0572 | 0.7487 | 0.040* | |
C5 | −0.26168 (9) | 0.12509 (13) | 0.69430 (9) | 0.0255 (3) | |
H5A | −0.2883 | 0.1930 | 0.6498 | 0.031* | |
H5B | −0.2530 | 0.1675 | 0.7570 | 0.031* | |
C6 | 0.05195 (9) | 0.02263 (11) | 0.70807 (8) | 0.0183 (2) | |
H6 | 0.0299 | 0.0345 | 0.7741 | 0.022* | |
C7 | 0.03092 (9) | −0.12561 (11) | 0.67320 (8) | 0.0184 (2) | |
H7A | 0.0196 | −0.1334 | 0.6042 | 0.022* | |
H7B | −0.0218 | −0.1712 | 0.7076 | 0.022* | |
C8 | 0.13952 (8) | −0.16661 (11) | 0.70825 (8) | 0.0170 (2) | |
C9 | 0.16442 (8) | −0.01080 (11) | 0.70776 (8) | 0.0185 (2) | |
H9A | 0.2012 | 0.0198 | 0.7650 | 0.022* | |
H9B | 0.1972 | 0.0192 | 0.6501 | 0.022* | |
C10 | −0.09240 (9) | 0.18804 (12) | 0.65933 (9) | 0.0217 (2) | |
H10A | −0.0951 | 0.2389 | 0.7190 | 0.026* | |
H10B | −0.1113 | 0.2493 | 0.6072 | 0.026* | |
C11 | 0.01471 (9) | 0.13877 (11) | 0.64581 (8) | 0.0189 (2) | |
C12 | 0.14055 (10) | −0.22104 (12) | 0.81163 (8) | 0.0227 (2) | |
H12A | 0.1028 | −0.1608 | 0.8512 | 0.034* | |
H12B | 0.2087 | −0.2262 | 0.8361 | 0.034* | |
H12C | 0.1109 | −0.3102 | 0.8122 | 0.034* | |
C13 | 0.19875 (8) | −0.25923 (11) | 0.64257 (7) | 0.0164 (2) | |
C14 | 0.15210 (8) | −0.37112 (11) | 0.59552 (8) | 0.0179 (2) | |
C15 | 0.20585 (9) | −0.45011 (12) | 0.53145 (8) | 0.0207 (2) | |
H15 | 0.1739 | −0.5233 | 0.5011 | 0.025* | |
C16 | 0.30558 (9) | −0.42308 (12) | 0.51144 (8) | 0.0214 (2) | |
C17 | 0.35248 (9) | −0.31813 (12) | 0.56246 (8) | 0.0201 (2) | |
H17 | 0.4200 | −0.3005 | 0.5522 | 0.024* | |
C18 | 0.30209 (8) | −0.23817 (11) | 0.62851 (8) | 0.0180 (2) | |
C19 | 0.04484 (9) | −0.41305 (12) | 0.61224 (9) | 0.0218 (2) | |
H19A | 0.0002 | −0.3601 | 0.5717 | 0.033* | |
H19B | 0.0295 | −0.3977 | 0.6783 | 0.033* | |
H19C | 0.0366 | −0.5080 | 0.5974 | 0.033* | |
C20 | 0.36053 (11) | −0.50581 (15) | 0.43835 (9) | 0.0302 (3) | |
H20A | 0.3376 | −0.4802 | 0.3748 | 0.045* | |
H20B | 0.3476 | −0.6009 | 0.4483 | 0.045* | |
H20C | 0.4314 | −0.4889 | 0.4454 | 0.045* | |
C21 | 0.36385 (9) | −0.13319 (12) | 0.68359 (9) | 0.0235 (3) | |
H21A | 0.4335 | −0.1585 | 0.6834 | 0.035* | |
H21B | 0.3420 | −0.1288 | 0.7486 | 0.035* | |
H21C | 0.3552 | −0.0456 | 0.6537 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0289 (5) | 0.0218 (4) | 0.0265 (4) | 0.0021 (4) | 0.0051 (3) | 0.0039 (3) |
N1 | 0.0210 (5) | 0.0184 (5) | 0.0179 (4) | 0.0020 (4) | 0.0022 (3) | −0.0004 (3) |
C1 | 0.0215 (5) | 0.0223 (6) | 0.0160 (5) | 0.0008 (4) | 0.0012 (4) | 0.0015 (4) |
C2 | 0.0255 (6) | 0.0273 (6) | 0.0221 (5) | −0.0037 (5) | 0.0026 (4) | −0.0024 (5) |
C3 | 0.0241 (6) | 0.0399 (8) | 0.0367 (7) | −0.0075 (6) | 0.0059 (5) | −0.0048 (6) |
C4 | 0.0290 (7) | 0.0381 (7) | 0.0336 (7) | −0.0042 (6) | 0.0144 (5) | −0.0051 (6) |
C5 | 0.0251 (6) | 0.0253 (6) | 0.0265 (6) | 0.0045 (5) | 0.0062 (5) | −0.0019 (5) |
C6 | 0.0211 (5) | 0.0169 (5) | 0.0169 (5) | 0.0015 (4) | 0.0009 (4) | −0.0009 (4) |
C7 | 0.0188 (5) | 0.0160 (5) | 0.0205 (5) | 0.0008 (4) | 0.0000 (4) | 0.0003 (4) |
C8 | 0.0191 (5) | 0.0157 (5) | 0.0162 (5) | 0.0003 (4) | −0.0007 (4) | −0.0006 (4) |
C9 | 0.0200 (5) | 0.0159 (5) | 0.0197 (5) | 0.0002 (4) | −0.0012 (4) | −0.0020 (4) |
C10 | 0.0235 (6) | 0.0161 (5) | 0.0255 (6) | 0.0035 (4) | −0.0003 (4) | 0.0000 (4) |
C11 | 0.0236 (6) | 0.0151 (5) | 0.0180 (5) | 0.0005 (4) | −0.0005 (4) | −0.0029 (4) |
C12 | 0.0291 (6) | 0.0216 (6) | 0.0174 (5) | 0.0037 (5) | 0.0008 (4) | 0.0010 (4) |
C13 | 0.0189 (5) | 0.0152 (5) | 0.0150 (5) | 0.0018 (4) | −0.0018 (4) | 0.0018 (4) |
C14 | 0.0206 (5) | 0.0162 (5) | 0.0166 (5) | 0.0010 (4) | −0.0023 (4) | 0.0017 (4) |
C15 | 0.0248 (6) | 0.0177 (5) | 0.0193 (5) | 0.0015 (4) | −0.0038 (4) | −0.0028 (4) |
C16 | 0.0255 (6) | 0.0214 (6) | 0.0172 (5) | 0.0058 (5) | −0.0009 (4) | 0.0001 (4) |
C17 | 0.0184 (5) | 0.0208 (5) | 0.0212 (5) | 0.0021 (4) | 0.0007 (4) | 0.0032 (4) |
C18 | 0.0198 (5) | 0.0160 (5) | 0.0180 (5) | 0.0007 (4) | −0.0019 (4) | 0.0023 (4) |
C19 | 0.0218 (6) | 0.0183 (5) | 0.0251 (6) | −0.0024 (4) | −0.0010 (4) | −0.0020 (4) |
C20 | 0.0314 (7) | 0.0333 (7) | 0.0260 (6) | 0.0076 (6) | 0.0017 (5) | −0.0079 (5) |
C21 | 0.0186 (5) | 0.0212 (6) | 0.0306 (6) | −0.0002 (4) | −0.0028 (4) | −0.0032 (5) |
Geometric parameters (Å, º) top
O1—C11 | 1.2154 (14) | C9—H9A | 0.9700 |
N1—C10 | 1.4549 (15) | C9—H9B | 0.9700 |
N1—C5 | 1.4657 (15) | C10—C11 | 1.5219 (16) |
N1—C1 | 1.4702 (14) | C10—H10A | 0.9700 |
C1—C2 | 1.5168 (17) | C10—H10B | 0.9700 |
C1—H1A | 0.9700 | C12—H12A | 0.9600 |
C1—H1B | 0.9700 | C12—H12B | 0.9600 |
C2—C3 | 1.5192 (18) | C12—H12C | 0.9600 |
C2—H2A | 0.9700 | C13—C18 | 1.4099 (15) |
C2—H2B | 0.9700 | C13—C14 | 1.4125 (15) |
C3—C4 | 1.524 (2) | C14—C15 | 1.3947 (16) |
C3—H3A | 0.9700 | C14—C19 | 1.5100 (16) |
C3—H3B | 0.9700 | C15—C16 | 1.3896 (17) |
C4—C5 | 1.5207 (19) | C15—H15 | 0.9300 |
C4—H4A | 0.9700 | C16—C17 | 1.3883 (17) |
C4—H4B | 0.9700 | C16—C20 | 1.5075 (16) |
C5—H5A | 0.9700 | C17—C18 | 1.3953 (16) |
C5—H5B | 0.9700 | C17—H17 | 0.9300 |
C6—C11 | 1.5064 (15) | C18—C21 | 1.5121 (16) |
C6—C9 | 1.5322 (15) | C19—H19A | 0.9600 |
C6—C7 | 1.5560 (15) | C19—H19B | 0.9600 |
C6—H6 | 0.9800 | C19—H19C | 0.9600 |
C7—C8 | 1.5639 (15) | C20—H20A | 0.9600 |
C7—H7A | 0.9700 | C20—H20B | 0.9600 |
C7—H7B | 0.9700 | C20—H20C | 0.9600 |
C8—C13 | 1.5250 (15) | C21—H21A | 0.9600 |
C8—C12 | 1.5344 (15) | C21—H21B | 0.9600 |
C8—C9 | 1.5642 (15) | C21—H21C | 0.9600 |
| | | |
C10—N1—C5 | 110.48 (9) | C6—C9—H9B | 113.6 |
C10—N1—C1 | 109.71 (9) | C8—C9—H9B | 113.6 |
C5—N1—C1 | 109.40 (9) | H9A—C9—H9B | 110.9 |
N1—C1—C2 | 110.90 (9) | N1—C10—C11 | 112.49 (9) |
N1—C1—H1A | 109.5 | N1—C10—H10A | 109.1 |
C2—C1—H1A | 109.5 | C11—C10—H10A | 109.1 |
N1—C1—H1B | 109.5 | N1—C10—H10B | 109.1 |
C2—C1—H1B | 109.5 | C11—C10—H10B | 109.1 |
H1A—C1—H1B | 108.0 | H10A—C10—H10B | 107.8 |
C1—C2—C3 | 110.22 (11) | O1—C11—C6 | 122.22 (11) |
C1—C2—H2A | 109.6 | O1—C11—C10 | 120.19 (10) |
C3—C2—H2A | 109.6 | C6—C11—C10 | 117.54 (10) |
C1—C2—H2B | 109.6 | C8—C12—H12A | 109.5 |
C3—C2—H2B | 109.6 | C8—C12—H12B | 109.5 |
H2A—C2—H2B | 108.1 | H12A—C12—H12B | 109.5 |
C2—C3—C4 | 110.13 (11) | C8—C12—H12C | 109.5 |
C2—C3—H3A | 109.6 | H12A—C12—H12C | 109.5 |
C4—C3—H3A | 109.6 | H12B—C12—H12C | 109.5 |
C2—C3—H3B | 109.6 | C18—C13—C14 | 117.81 (10) |
C4—C3—H3B | 109.6 | C18—C13—C8 | 121.29 (10) |
H3A—C3—H3B | 108.1 | C14—C13—C8 | 120.88 (10) |
C5—C4—C3 | 111.22 (11) | C15—C14—C13 | 120.11 (10) |
C5—C4—H4A | 109.4 | C15—C14—C19 | 116.88 (10) |
C3—C4—H4A | 109.4 | C13—C14—C19 | 123.00 (10) |
C5—C4—H4B | 109.4 | C16—C15—C14 | 122.21 (11) |
C3—C4—H4B | 109.4 | C16—C15—H15 | 118.9 |
H4A—C4—H4B | 108.0 | C14—C15—H15 | 118.9 |
N1—C5—C4 | 110.30 (10) | C17—C16—C15 | 117.16 (11) |
N1—C5—H5A | 109.6 | C17—C16—C20 | 121.66 (11) |
C4—C5—H5A | 109.6 | C15—C16—C20 | 121.18 (11) |
N1—C5—H5B | 109.6 | C16—C17—C18 | 122.45 (11) |
C4—C5—H5B | 109.6 | C16—C17—H17 | 118.8 |
H5A—C5—H5B | 108.1 | C18—C17—H17 | 118.8 |
C11—C6—C9 | 117.71 (10) | C17—C18—C13 | 119.92 (10) |
C11—C6—C7 | 118.34 (9) | C17—C18—C21 | 116.90 (10) |
C9—C6—C7 | 88.03 (8) | C13—C18—C21 | 123.17 (10) |
C11—C6—H6 | 110.3 | C14—C19—H19A | 109.5 |
C9—C6—H6 | 110.3 | C14—C19—H19B | 109.5 |
C7—C6—H6 | 110.3 | H19A—C19—H19B | 109.5 |
C6—C7—C8 | 89.27 (8) | C14—C19—H19C | 109.5 |
C6—C7—H7A | 113.8 | H19A—C19—H19C | 109.5 |
C8—C7—H7A | 113.8 | H19B—C19—H19C | 109.5 |
C6—C7—H7B | 113.8 | C16—C20—H20A | 109.5 |
C8—C7—H7B | 113.8 | C16—C20—H20B | 109.5 |
H7A—C7—H7B | 111.0 | H20A—C20—H20B | 109.5 |
C13—C8—C12 | 111.37 (9) | C16—C20—H20C | 109.5 |
C13—C8—C7 | 117.09 (9) | H20A—C20—H20C | 109.5 |
C12—C8—C7 | 111.38 (9) | H20B—C20—H20C | 109.5 |
C13—C8—C9 | 117.80 (9) | C18—C21—H21A | 109.5 |
C12—C8—C9 | 110.38 (9) | C18—C21—H21B | 109.5 |
C7—C8—C9 | 86.63 (8) | H21A—C21—H21B | 109.5 |
C6—C9—C8 | 90.13 (8) | C18—C21—H21C | 109.5 |
C6—C9—H9A | 113.6 | H21A—C21—H21C | 109.5 |
C8—C9—H9A | 113.6 | H21B—C21—H21C | 109.5 |
| | | |
C10—N1—C1—C2 | 176.18 (9) | N1—C10—C11—O1 | 134.98 (11) |
C5—N1—C1—C2 | −62.47 (12) | N1—C10—C11—C6 | −47.46 (13) |
N1—C1—C2—C3 | 58.48 (13) | C12—C8—C13—C18 | −90.74 (12) |
C1—C2—C3—C4 | −53.05 (15) | C7—C8—C13—C18 | 139.49 (10) |
C2—C3—C4—C5 | 52.90 (16) | C9—C8—C13—C18 | 38.24 (14) |
C10—N1—C5—C4 | −177.78 (10) | C12—C8—C13—C14 | 87.76 (12) |
C1—N1—C5—C4 | 61.34 (13) | C7—C8—C13—C14 | −42.01 (14) |
C3—C4—C5—N1 | −57.30 (15) | C9—C8—C13—C14 | −143.25 (10) |
C11—C6—C7—C8 | 139.09 (10) | C18—C13—C14—C15 | −5.11 (15) |
C9—C6—C7—C8 | 18.42 (8) | C8—C13—C14—C15 | 176.33 (10) |
C6—C7—C8—C13 | −137.71 (10) | C18—C13—C14—C19 | 173.77 (10) |
C6—C7—C8—C12 | 92.53 (10) | C8—C13—C14—C19 | −4.79 (16) |
C6—C7—C8—C9 | −18.06 (8) | C13—C14—C15—C16 | 0.06 (17) |
C11—C6—C9—C8 | −139.64 (10) | C19—C14—C15—C16 | −178.89 (10) |
C7—C6—C9—C8 | −18.42 (8) | C14—C15—C16—C17 | 3.79 (17) |
C13—C8—C9—C6 | 137.33 (9) | C14—C15—C16—C20 | −177.03 (11) |
C12—C8—C9—C6 | −93.22 (10) | C15—C16—C17—C18 | −2.55 (17) |
C7—C8—C9—C6 | 18.34 (8) | C20—C16—C17—C18 | 178.27 (11) |
C5—N1—C10—C11 | 168.37 (9) | C16—C17—C18—C13 | −2.52 (17) |
C1—N1—C10—C11 | −70.94 (12) | C16—C17—C18—C21 | 176.27 (11) |
C9—C6—C11—O1 | 8.08 (16) | C14—C13—C18—C17 | 6.29 (15) |
C7—C6—C11—O1 | −95.75 (14) | C8—C13—C18—C17 | −175.16 (10) |
C9—C6—C11—C10 | −169.43 (9) | C14—C13—C18—C21 | −172.43 (10) |
C7—C6—C11—C10 | 86.74 (12) | C8—C13—C18—C21 | 6.12 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9B···O1 | 0.97 | 2.57 | 2.8903 (14) | 100 |
C1—H1A···O1i | 0.97 | 2.65 | 3.3508 (15) | 130 |
C9—H9A···Cg1ii | 0.97 | 2.61 | 3.5435 (14) | 160 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2. |