In the title compound, C
14H
17NO, 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
CCDC reference: 633637
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C14H17NO | F(000) = 464 |
Mr = 215.29 | Dx = 1.223 Mg m−3 |
Monoclinic, P21/c | Melting point = 340–343 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.006 (2) Å | Cell parameters from 979 reflections |
b = 9.441 (3) Å | θ = 2.6–27.7° |
c = 15.535 (4) Å | µ = 0.08 mm−1 |
β = 95.197 (6)° | T = 173 K |
V = 1169.5 (6) Å3 | Block, pale brown |
Z = 4 | 0.38 × 0.28 × 0.24 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1563 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.037 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 25.5°, θmin = 2.5° |
Tmin = 0.962, Tmax = 0.982 | h = −9→9 |
5068 measured reflections | k = −9→11 |
2178 independent reflections | l = −18→14 |
Refinement top
Refinement on F2 | 205 restraints |
Least-squares matrix: full | H-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 = 1.06 | Δρmax = 0.24 e Å−3 |
2178 reflections | Δρmin = −0.34 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C2 | 0.4632 (2) | 0.2460 (2) | 0.49237 (12) | 0.0264 (5) | |
C3 | 0.3064 (3) | 0.2206 (3) | 0.53690 (13) | 0.0355 (5) | |
H3A | 0.2715 | 0.3107 | 0.5625 | 0.043* | 0.607 (6) |
H3B | 0.3318 | 0.1523 | 0.5846 | 0.043* | 0.607 (6) |
H3C | 0.229 | 0.3014 | 0.5248 | 0.043* | 0.393 (6) |
H3D | 0.3364 | 0.2173 | 0.6001 | 0.043* | 0.393 (6) |
C4A | 0.1590 (4) | 0.1624 (4) | 0.4753 (2) | 0.0338 (10) | 0.607 (6) |
H4A1 | 0.0643 | 0.1356 | 0.5087 | 0.041* | 0.607 (6) |
H4A2 | 0.1194 | 0.236 | 0.4328 | 0.041* | 0.607 (6) |
C5A | 0.2206 (6) | 0.0339 (5) | 0.4288 (3) | 0.0378 (11) | 0.607 (6) |
H5A1 | 0.1266 | −0.0111 | 0.393 | 0.045* | 0.607 (6) |
H5A2 | 0.2692 | −0.0366 | 0.4711 | 0.045* | 0.607 (6) |
C4B | 0.2162 (8) | 0.0849 (7) | 0.5090 (3) | 0.0420 (18) | 0.393 (6) |
H4B1 | 0.1093 | 0.0765 | 0.536 | 0.05* | 0.393 (6) |
H4B2 | 0.2868 | 0.0013 | 0.5254 | 0.05* | 0.393 (6) |
C5B | 0.1842 (7) | 0.0962 (10) | 0.4113 (4) | 0.0401 (18) | 0.393 (6) |
H5B1 | 0.1298 | 0.1879 | 0.3954 | 0.048* | 0.393 (6) |
H5B2 | 0.1088 | 0.019 | 0.3889 | 0.048* | 0.393 (6) |
C6 | 0.3532 (3) | 0.0854 (3) | 0.37209 (14) | 0.0366 (6) | |
H6A | 0.4163 | 0.0025 | 0.3533 | 0.044* | 0.607 (6) |
H6B | 0.2962 | 0.1298 | 0.3196 | 0.044* | 0.607 (6) |
H6C | 0.3984 | −0.0117 | 0.3802 | 0.044* | 0.393 (6) |
H6D | 0.3368 | 0.1048 | 0.3093 | 0.044* | 0.393 (6) |
C7 | 0.6145 (3) | 0.2210 (3) | 0.36359 (14) | 0.0369 (6) | |
H7A | 0.6017 | 0.1699 | 0.3085 | 0.055* | |
H7B | 0.7196 | 0.1924 | 0.3962 | 0.055* | |
H7C | 0.6169 | 0.3232 | 0.3525 | 0.055* | |
C8 | 0.5942 (2) | 0.3273 (2) | 0.53132 (13) | 0.0288 (5) | |
H8 | 0.6911 | 0.3377 | 0.5008 | 0.035* | |
C9 | 0.5953 (2) | 0.3961 (2) | 0.61296 (12) | 0.0279 (5) | |
C10 | 0.7548 (2) | 0.4703 (2) | 0.64782 (12) | 0.0267 (5) | |
C11 | 0.7452 (3) | 0.5667 (2) | 0.71523 (12) | 0.0326 (5) | |
H11 | 0.6399 | 0.5847 | 0.7367 | 0.039* | |
C12 | 0.8861 (3) | 0.6365 (3) | 0.75130 (13) | 0.0365 (5) | |
H12 | 0.8767 | 0.7027 | 0.7966 | 0.044* | |
C13 | 1.0406 (3) | 0.6102 (2) | 0.72174 (13) | 0.0357 (5) | |
H13 | 1.1376 | 0.6581 | 0.7467 | 0.043* | |
C14 | 1.0535 (3) | 0.5139 (2) | 0.65557 (15) | 0.0382 (6) | |
H14 | 1.1598 | 0.495 | 0.6354 | 0.046* | |
C15 | 0.9121 (2) | 0.4451 (2) | 0.61866 (14) | 0.0336 (5) | |
H15 | 0.9222 | 0.3799 | 0.5729 | 0.04* | |
N1 | 0.4733 (2) | 0.18768 (19) | 0.41371 (11) | 0.0311 (5) | |
O1 | 0.47471 (18) | 0.40113 (18) | 0.65909 (9) | 0.0412 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0262 (10) | 0.0293 (11) | 0.0245 (10) | 0.0030 (8) | 0.0069 (8) | 0.0023 (8) |
C3 | 0.0286 (11) | 0.0471 (13) | 0.0322 (11) | −0.0085 (9) | 0.0112 (9) | −0.0064 (9) |
C4A | 0.0268 (17) | 0.041 (2) | 0.034 (2) | −0.0064 (16) | 0.0062 (15) | −0.0007 (17) |
C5A | 0.044 (2) | 0.035 (3) | 0.036 (2) | −0.0089 (19) | 0.0073 (18) | −0.0006 (18) |
C4B | 0.042 (3) | 0.052 (4) | 0.033 (3) | −0.019 (3) | 0.009 (2) | 0.001 (3) |
C5B | 0.035 (3) | 0.049 (5) | 0.037 (3) | −0.020 (3) | 0.005 (3) | −0.002 (3) |
C6 | 0.0361 (12) | 0.0426 (13) | 0.0318 (11) | −0.0089 (9) | 0.0065 (9) | −0.0068 (9) |
C7 | 0.0312 (11) | 0.0520 (14) | 0.0293 (11) | −0.0066 (10) | 0.0121 (9) | −0.0081 (10) |
C8 | 0.0233 (10) | 0.0362 (12) | 0.0279 (10) | −0.0012 (8) | 0.0082 (8) | 0.0003 (8) |
C9 | 0.0233 (10) | 0.0341 (12) | 0.0270 (10) | 0.0024 (8) | 0.0065 (8) | 0.0046 (8) |
C10 | 0.0294 (10) | 0.0285 (11) | 0.0225 (10) | 0.0024 (8) | 0.0035 (8) | 0.0055 (8) |
C11 | 0.0334 (11) | 0.0404 (12) | 0.0249 (10) | −0.0004 (9) | 0.0081 (8) | 0.0015 (8) |
C12 | 0.0415 (12) | 0.0437 (13) | 0.0248 (11) | −0.0053 (10) | 0.0052 (9) | −0.0033 (9) |
C13 | 0.0333 (11) | 0.0400 (13) | 0.0330 (12) | −0.0078 (10) | −0.0016 (9) | 0.0037 (9) |
C14 | 0.0300 (11) | 0.0413 (13) | 0.0441 (13) | 0.0003 (9) | 0.0075 (9) | −0.0003 (10) |
C15 | 0.0302 (11) | 0.0338 (12) | 0.0373 (12) | 0.0012 (8) | 0.0053 (9) | −0.0040 (9) |
N1 | 0.0296 (9) | 0.0394 (11) | 0.0252 (9) | −0.0043 (7) | 0.0081 (7) | −0.0033 (7) |
O1 | 0.0312 (8) | 0.0633 (12) | 0.0304 (8) | −0.0060 (7) | 0.0096 (6) | −0.0112 (7) |
Geometric parameters (Å, º) top
C2—N1 | 1.350 (3) | C6—H6B | 0.99 |
C2—C8 | 1.393 (3) | C6—H6C | 0.99 |
C2—C3 | 1.506 (3) | C6—H6D | 0.99 |
C3—C4B | 1.515 (5) | C7—N1 | 1.464 (2) |
C3—C4A | 1.551 (4) | C7—H7A | 0.98 |
C3—H3A | 0.99 | C7—H7B | 0.98 |
C3—H3B | 0.99 | C7—H7C | 0.98 |
C3—H3C | 0.99 | C8—C9 | 1.424 (3) |
C3—H3D | 0.99 | C8—H8 | 0.95 |
C4A—C5A | 1.518 (5) | C9—O1 | 1.255 (2) |
C4A—H4A1 | 0.99 | C9—C10 | 1.513 (3) |
C4A—H4A2 | 0.99 | C10—C11 | 1.395 (3) |
C5A—C6 | 1.520 (4) | C10—C15 | 1.397 (3) |
C5A—H5A1 | 0.99 | C11—C12 | 1.380 (3) |
C5A—H5A2 | 0.99 | C11—H11 | 0.95 |
C4B—C5B | 1.520 (6) | C12—C13 | 1.380 (3) |
C4B—H4B1 | 0.99 | C12—H12 | 0.95 |
C4B—H4B2 | 0.99 | C13—C14 | 1.383 (3) |
C5B—C6 | 1.537 (5) | C13—H13 | 0.95 |
C5B—H5B1 | 0.99 | C14—C15 | 1.384 (3) |
C5B—H5B2 | 0.99 | C14—H14 | 0.95 |
C6—N1 | 1.470 (3) | C15—H15 | 0.95 |
C6—H6A | 0.99 | | |
| | | |
N1—C2—C8 | 120.91 (18) | C5A—C6—H6A | 108.6 |
N1—C2—C3 | 118.14 (17) | N1—C6—H6B | 108.6 |
C8—C2—C3 | 120.96 (17) | C5A—C6—H6B | 108.6 |
C2—C3—C4B | 113.5 (3) | H6A—C6—H6B | 107.6 |
C2—C3—C4A | 113.09 (19) | N1—C6—H6C | 109.6 |
C2—C3—H3A | 109 | C5B—C6—H6C | 109.6 |
C4A—C3—H3A | 109 | N1—C6—H6D | 109.6 |
C2—C3—H3B | 109 | C5B—C6—H6D | 109.6 |
C4A—C3—H3B | 109 | H6C—C6—H6D | 108.1 |
H3A—C3—H3B | 107.8 | N1—C7—H7A | 109.5 |
C2—C3—H3C | 108.9 | N1—C7—H7B | 109.5 |
C4B—C3—H3C | 108.9 | H7A—C7—H7B | 109.5 |
C2—C3—H3D | 108.9 | N1—C7—H7C | 109.5 |
C4B—C3—H3D | 108.9 | H7A—C7—H7C | 109.5 |
H3C—C3—H3D | 107.7 | H7B—C7—H7C | 109.5 |
C5A—C4A—C3 | 108.3 (3) | C2—C8—C9 | 125.59 (18) |
C5A—C4A—H4A1 | 110 | C2—C8—H8 | 117.2 |
C3—C4A—H4A1 | 110 | C9—C8—H8 | 117.2 |
C5A—C4A—H4A2 | 110 | O1—C9—C8 | 125.65 (18) |
C3—C4A—H4A2 | 110 | O1—C9—C10 | 116.50 (17) |
H4A1—C4A—H4A2 | 108.4 | C8—C9—C10 | 117.85 (17) |
C4A—C5A—C6 | 107.1 (3) | C11—C10—C15 | 117.83 (19) |
C4A—C5A—H5A1 | 110.3 | C11—C10—C9 | 117.98 (18) |
C6—C5A—H5A1 | 110.3 | C15—C10—C9 | 124.16 (18) |
C4A—C5A—H5A2 | 110.3 | C12—C11—C10 | 121.2 (2) |
C6—C5A—H5A2 | 110.3 | C12—C11—H11 | 119.4 |
H5A1—C5A—H5A2 | 108.5 | C10—C11—H11 | 119.4 |
C3—C4B—C5B | 105.0 (5) | C13—C12—C11 | 120.2 (2) |
C3—C4B—H4B1 | 110.7 | C13—C12—H12 | 119.9 |
C5B—C4B—H4B1 | 110.7 | C11—C12—H12 | 119.9 |
C3—C4B—H4B2 | 110.7 | C12—C13—C14 | 119.6 (2) |
C5B—C4B—H4B2 | 110.7 | C12—C13—H13 | 120.2 |
H4B1—C4B—H4B2 | 108.8 | C14—C13—H13 | 120.2 |
C4B—C5B—C6 | 108.4 (5) | C13—C14—C15 | 120.2 (2) |
C4B—C5B—H5B1 | 110 | C13—C14—H14 | 119.9 |
C6—C5B—H5B1 | 110 | C15—C14—H14 | 119.9 |
C4B—C5B—H5B2 | 110 | C14—C15—C10 | 120.9 (2) |
C6—C5B—H5B2 | 110 | C14—C15—H15 | 119.5 |
H5B1—C5B—H5B2 | 108.4 | C10—C15—H15 | 119.5 |
N1—C6—C5A | 114.7 (2) | C2—N1—C7 | 120.42 (17) |
N1—C6—C5B | 110.3 (3) | C2—N1—C6 | 125.16 (17) |
N1—C6—H6A | 108.6 | C7—N1—C6 | 114.39 (16) |
| | | |
N1—C2—C3—C4B | 26.1 (4) | C8—C9—C10—C11 | 164.01 (19) |
C8—C2—C3—C4B | −153.8 (4) | O1—C9—C10—C15 | 162.0 (2) |
N1—C2—C3—C4A | −15.0 (3) | C8—C9—C10—C15 | −18.1 (3) |
C8—C2—C3—C4A | 165.1 (2) | C15—C10—C11—C12 | 0.8 (3) |
C2—C3—C4A—C5A | 52.2 (4) | C9—C10—C11—C12 | 178.82 (19) |
C4B—C3—C4A—C5A | −46.8 (4) | C10—C11—C12—C13 | −0.9 (3) |
C3—C4A—C5A—C6 | −65.2 (4) | C11—C12—C13—C14 | 0.2 (3) |
C2—C3—C4B—C5B | −55.6 (6) | C12—C13—C14—C15 | 0.6 (3) |
C4A—C3—C4B—C5B | 42.2 (4) | C13—C14—C15—C10 | −0.6 (3) |
C3—C4B—C5B—C6 | 69.1 (7) | C11—C10—C15—C14 | −0.1 (3) |
C4A—C5A—C6—N1 | 43.5 (4) | C9—C10—C15—C14 | −177.94 (19) |
C4A—C5A—C6—C5B | −42.5 (6) | C8—C2—N1—C7 | −6.6 (3) |
C4B—C5B—C6—N1 | −52.1 (7) | C3—C2—N1—C7 | 173.54 (18) |
C4B—C5B—C6—C5A | 53.0 (6) | C8—C2—N1—C6 | 171.43 (19) |
N1—C2—C8—C9 | 178.57 (19) | C3—C2—N1—C6 | −8.5 (3) |
C3—C2—C8—C9 | −1.5 (3) | C5A—C6—N1—C2 | −6.6 (4) |
C2—C8—C9—O1 | −4.9 (3) | C5B—C6—N1—C2 | 21.7 (4) |
C2—C8—C9—C10 | 175.31 (19) | C5A—C6—N1—C7 | 171.5 (3) |
O1—C9—C10—C11 | −15.8 (3) | C5B—C6—N1—C7 | −160.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3D···O1 | 0.99 | 2.21 | 2.804 (3) | 117 |
C7—H7A···O1i | 0.98 | 2.54 | 3.469 (3) | 159 |
Symmetry code: (i) x, −y+1/2, z−1/2. |