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In the title compound, C14H17NO, the piperidine ring is in a half-chair conformation. The mol­ecules are linked into C(7) chains by an inter­molecular C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605152X/bx2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605152X/bx2042Isup2.hkl
Contains datablock I

CCDC reference: 633637

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.051
  • wR factor = 0.199
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker (1999); 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) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

(2E)-2-(1-Methylpiperidin-2-ylidene)-1-phenylethanone top
Crystal data top
C14H17NOF(000) = 464
Mr = 215.29Dx = 1.223 Mg m3
Monoclinic, P21/cMelting point = 340–343 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.006 (2) ÅCell parameters from 979 reflections
b = 9.441 (3) Åθ = 2.6–27.7°
c = 15.535 (4) ŵ = 0.08 mm1
β = 95.197 (6)°T = 173 K
V = 1169.5 (6) Å3Block, pale brown
Z = 40.38 × 0.28 × 0.24 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1563 reflections with I > 2σ(I)
φ and ω scansRint = 0.037
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 25.5°, θmin = 2.5°
Tmin = 0.962, Tmax = 0.982h = 99
5068 measured reflectionsk = 911
2178 independent reflectionsl = 1814
Refinement top
Refinement on F2205 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.1371P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.199(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.24 e Å3
2178 reflectionsΔρmin = 0.34 e Å3
164 parameters
Special details top

Experimental. absorption corrections were made using the program SADABS (Sheldrick, 1996).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C20.4632 (2)0.2460 (2)0.49237 (12)0.0264 (5)
C30.3064 (3)0.2206 (3)0.53690 (13)0.0355 (5)
H3A0.27150.31070.56250.043*0.607 (6)
H3B0.33180.15230.58460.043*0.607 (6)
H3C0.2290.30140.52480.043*0.393 (6)
H3D0.33640.21730.60010.043*0.393 (6)
C4A0.1590 (4)0.1624 (4)0.4753 (2)0.0338 (10)0.607 (6)
H4A10.06430.13560.50870.041*0.607 (6)
H4A20.11940.2360.43280.041*0.607 (6)
C5A0.2206 (6)0.0339 (5)0.4288 (3)0.0378 (11)0.607 (6)
H5A10.12660.01110.3930.045*0.607 (6)
H5A20.26920.03660.47110.045*0.607 (6)
C4B0.2162 (8)0.0849 (7)0.5090 (3)0.0420 (18)0.393 (6)
H4B10.10930.07650.5360.05*0.393 (6)
H4B20.28680.00130.52540.05*0.393 (6)
C5B0.1842 (7)0.0962 (10)0.4113 (4)0.0401 (18)0.393 (6)
H5B10.12980.18790.39540.048*0.393 (6)
H5B20.10880.0190.38890.048*0.393 (6)
C60.3532 (3)0.0854 (3)0.37209 (14)0.0366 (6)
H6A0.41630.00250.35330.044*0.607 (6)
H6B0.29620.12980.31960.044*0.607 (6)
H6C0.39840.01170.38020.044*0.393 (6)
H6D0.33680.10480.30930.044*0.393 (6)
C70.6145 (3)0.2210 (3)0.36359 (14)0.0369 (6)
H7A0.60170.16990.30850.055*
H7B0.71960.19240.39620.055*
H7C0.61690.32320.35250.055*
C80.5942 (2)0.3273 (2)0.53132 (13)0.0288 (5)
H80.69110.33770.50080.035*
C90.5953 (2)0.3961 (2)0.61296 (12)0.0279 (5)
C100.7548 (2)0.4703 (2)0.64782 (12)0.0267 (5)
C110.7452 (3)0.5667 (2)0.71523 (12)0.0326 (5)
H110.63990.58470.73670.039*
C120.8861 (3)0.6365 (3)0.75130 (13)0.0365 (5)
H120.87670.70270.79660.044*
C131.0406 (3)0.6102 (2)0.72174 (13)0.0357 (5)
H131.13760.65810.74670.043*
C141.0535 (3)0.5139 (2)0.65557 (15)0.0382 (6)
H141.15980.4950.63540.046*
C150.9121 (2)0.4451 (2)0.61866 (14)0.0336 (5)
H150.92220.37990.57290.04*
N10.4733 (2)0.18768 (19)0.41371 (11)0.0311 (5)
O10.47471 (18)0.40113 (18)0.65909 (9)0.0412 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0262 (10)0.0293 (11)0.0245 (10)0.0030 (8)0.0069 (8)0.0023 (8)
C30.0286 (11)0.0471 (13)0.0322 (11)0.0085 (9)0.0112 (9)0.0064 (9)
C4A0.0268 (17)0.041 (2)0.034 (2)0.0064 (16)0.0062 (15)0.0007 (17)
C5A0.044 (2)0.035 (3)0.036 (2)0.0089 (19)0.0073 (18)0.0006 (18)
C4B0.042 (3)0.052 (4)0.033 (3)0.019 (3)0.009 (2)0.001 (3)
C5B0.035 (3)0.049 (5)0.037 (3)0.020 (3)0.005 (3)0.002 (3)
C60.0361 (12)0.0426 (13)0.0318 (11)0.0089 (9)0.0065 (9)0.0068 (9)
C70.0312 (11)0.0520 (14)0.0293 (11)0.0066 (10)0.0121 (9)0.0081 (10)
C80.0233 (10)0.0362 (12)0.0279 (10)0.0012 (8)0.0082 (8)0.0003 (8)
C90.0233 (10)0.0341 (12)0.0270 (10)0.0024 (8)0.0065 (8)0.0046 (8)
C100.0294 (10)0.0285 (11)0.0225 (10)0.0024 (8)0.0035 (8)0.0055 (8)
C110.0334 (11)0.0404 (12)0.0249 (10)0.0004 (9)0.0081 (8)0.0015 (8)
C120.0415 (12)0.0437 (13)0.0248 (11)0.0053 (10)0.0052 (9)0.0033 (9)
C130.0333 (11)0.0400 (13)0.0330 (12)0.0078 (10)0.0016 (9)0.0037 (9)
C140.0300 (11)0.0413 (13)0.0441 (13)0.0003 (9)0.0075 (9)0.0003 (10)
C150.0302 (11)0.0338 (12)0.0373 (12)0.0012 (8)0.0053 (9)0.0040 (9)
N10.0296 (9)0.0394 (11)0.0252 (9)0.0043 (7)0.0081 (7)0.0033 (7)
O10.0312 (8)0.0633 (12)0.0304 (8)0.0060 (7)0.0096 (6)0.0112 (7)
Geometric parameters (Å, º) top
C2—N11.350 (3)C6—H6B0.99
C2—C81.393 (3)C6—H6C0.99
C2—C31.506 (3)C6—H6D0.99
C3—C4B1.515 (5)C7—N11.464 (2)
C3—C4A1.551 (4)C7—H7A0.98
C3—H3A0.99C7—H7B0.98
C3—H3B0.99C7—H7C0.98
C3—H3C0.99C8—C91.424 (3)
C3—H3D0.99C8—H80.95
C4A—C5A1.518 (5)C9—O11.255 (2)
C4A—H4A10.99C9—C101.513 (3)
C4A—H4A20.99C10—C111.395 (3)
C5A—C61.520 (4)C10—C151.397 (3)
C5A—H5A10.99C11—C121.380 (3)
C5A—H5A20.99C11—H110.95
C4B—C5B1.520 (6)C12—C131.380 (3)
C4B—H4B10.99C12—H120.95
C4B—H4B20.99C13—C141.383 (3)
C5B—C61.537 (5)C13—H130.95
C5B—H5B10.99C14—C151.384 (3)
C5B—H5B20.99C14—H140.95
C6—N11.470 (3)C15—H150.95
C6—H6A0.99
N1—C2—C8120.91 (18)C5A—C6—H6A108.6
N1—C2—C3118.14 (17)N1—C6—H6B108.6
C8—C2—C3120.96 (17)C5A—C6—H6B108.6
C2—C3—C4B113.5 (3)H6A—C6—H6B107.6
C2—C3—C4A113.09 (19)N1—C6—H6C109.6
C2—C3—H3A109C5B—C6—H6C109.6
C4A—C3—H3A109N1—C6—H6D109.6
C2—C3—H3B109C5B—C6—H6D109.6
C4A—C3—H3B109H6C—C6—H6D108.1
H3A—C3—H3B107.8N1—C7—H7A109.5
C2—C3—H3C108.9N1—C7—H7B109.5
C4B—C3—H3C108.9H7A—C7—H7B109.5
C2—C3—H3D108.9N1—C7—H7C109.5
C4B—C3—H3D108.9H7A—C7—H7C109.5
H3C—C3—H3D107.7H7B—C7—H7C109.5
C5A—C4A—C3108.3 (3)C2—C8—C9125.59 (18)
C5A—C4A—H4A1110C2—C8—H8117.2
C3—C4A—H4A1110C9—C8—H8117.2
C5A—C4A—H4A2110O1—C9—C8125.65 (18)
C3—C4A—H4A2110O1—C9—C10116.50 (17)
H4A1—C4A—H4A2108.4C8—C9—C10117.85 (17)
C4A—C5A—C6107.1 (3)C11—C10—C15117.83 (19)
C4A—C5A—H5A1110.3C11—C10—C9117.98 (18)
C6—C5A—H5A1110.3C15—C10—C9124.16 (18)
C4A—C5A—H5A2110.3C12—C11—C10121.2 (2)
C6—C5A—H5A2110.3C12—C11—H11119.4
H5A1—C5A—H5A2108.5C10—C11—H11119.4
C3—C4B—C5B105.0 (5)C13—C12—C11120.2 (2)
C3—C4B—H4B1110.7C13—C12—H12119.9
C5B—C4B—H4B1110.7C11—C12—H12119.9
C3—C4B—H4B2110.7C12—C13—C14119.6 (2)
C5B—C4B—H4B2110.7C12—C13—H13120.2
H4B1—C4B—H4B2108.8C14—C13—H13120.2
C4B—C5B—C6108.4 (5)C13—C14—C15120.2 (2)
C4B—C5B—H5B1110C13—C14—H14119.9
C6—C5B—H5B1110C15—C14—H14119.9
C4B—C5B—H5B2110C14—C15—C10120.9 (2)
C6—C5B—H5B2110C14—C15—H15119.5
H5B1—C5B—H5B2108.4C10—C15—H15119.5
N1—C6—C5A114.7 (2)C2—N1—C7120.42 (17)
N1—C6—C5B110.3 (3)C2—N1—C6125.16 (17)
N1—C6—H6A108.6C7—N1—C6114.39 (16)
N1—C2—C3—C4B26.1 (4)C8—C9—C10—C11164.01 (19)
C8—C2—C3—C4B153.8 (4)O1—C9—C10—C15162.0 (2)
N1—C2—C3—C4A15.0 (3)C8—C9—C10—C1518.1 (3)
C8—C2—C3—C4A165.1 (2)C15—C10—C11—C120.8 (3)
C2—C3—C4A—C5A52.2 (4)C9—C10—C11—C12178.82 (19)
C4B—C3—C4A—C5A46.8 (4)C10—C11—C12—C130.9 (3)
C3—C4A—C5A—C665.2 (4)C11—C12—C13—C140.2 (3)
C2—C3—C4B—C5B55.6 (6)C12—C13—C14—C150.6 (3)
C4A—C3—C4B—C5B42.2 (4)C13—C14—C15—C100.6 (3)
C3—C4B—C5B—C669.1 (7)C11—C10—C15—C140.1 (3)
C4A—C5A—C6—N143.5 (4)C9—C10—C15—C14177.94 (19)
C4A—C5A—C6—C5B42.5 (6)C8—C2—N1—C76.6 (3)
C4B—C5B—C6—N152.1 (7)C3—C2—N1—C7173.54 (18)
C4B—C5B—C6—C5A53.0 (6)C8—C2—N1—C6171.43 (19)
N1—C2—C8—C9178.57 (19)C3—C2—N1—C68.5 (3)
C3—C2—C8—C91.5 (3)C5A—C6—N1—C26.6 (4)
C2—C8—C9—O14.9 (3)C5B—C6—N1—C221.7 (4)
C2—C8—C9—C10175.31 (19)C5A—C6—N1—C7171.5 (3)
O1—C9—C10—C1115.8 (3)C5B—C6—N1—C7160.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3D···O10.992.212.804 (3)117
C7—H7A···O1i0.982.543.469 (3)159
Symmetry code: (i) x, y+1/2, z1/2.
 

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