1-Acetyl-2-phenylper­hydro­quinolin-4-yl acetate

The piperidine and cyclo­hexane rings in the title compound, C₁₉H₂₅NO₃, are trans-fused and adopt boat and chair conformations, respectively. The phenyl and ester substituents are oriented axially with respect to the deca­hydro­quinoline moiety. The N atom of the piperidine ring exists in a planar configuration. The keto O atom of the ester group exhibits positional disorder, with an 80:20 population ratio. The crystal structure is stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.154
• Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.32 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C42
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A    ..  O12     ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13C   ..  O12     ..       2.78 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1-Acetyl-2-phenyl-4-acetoxy-decahydroquinoline

Crystal data

C19H25NO3	Z = 2
Mr = 315.40	F(000) = 340
Triclinic, P1	Dx = 1.174 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.856 (1) Å	Cell parameters from 25 reflections
b = 9.050 (2) Å	θ = 10–20°
c = 12.343 (1) Å	µ = 0.08 mm^−1
α = 85.35 (1)°	T = 293 K
β = 87.82 (1)°	Prism, colourless
γ = 64.82 (1)°	0.42 × 0.38 × 0.30 mm
V = 892.3 (2) Å^3

Data collection

Enraf-Nonius CAD4 diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 2.5°
Graphite monochromator	h = −1→11
ω/2θ scans	k = −11→11
4839 measured reflections	l = −16→16
4056 independent reflections	2 standard reflections every 100 reflections
2925 reflections with I > 2σ(I)	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0836P)^2 + 0.0334P] where P = (Fo^2 + 2Fc^2)/3
4056 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.02979 (14)	0.71921 (14)	0.37956 (8)	0.0418 (3)
C2	−0.09576 (16)	0.76641 (16)	0.29334 (10)	0.0411 (3)
H2	−0.2011	0.7813	0.3297	0.049*
C3	−0.04910 (18)	0.62145 (17)	0.22372 (11)	0.0474 (3)
H3A	−0.0555	0.5307	0.2680	0.057*
H3B	−0.1297	0.6516	0.1655	0.057*
C4	0.12486 (19)	0.56558 (16)	0.17455 (11)	0.0482 (3)
H4	0.1160	0.5924	0.0958	0.058*
C5	0.4114 (2)	0.5621 (2)	0.19180 (16)	0.0678 (5)
H5A	0.4607	0.4495	0.2221	0.081*
H5B	0.4217	0.5612	0.1133	0.081*
C6	0.5043 (2)	0.6516 (3)	0.2326 (2)	0.0857 (7)
H6A	0.4647	0.7597	0.1952	0.103*
H6B	0.6221	0.5930	0.2163	0.103*
C7	0.4814 (2)	0.6678 (3)	0.3535 (2)	0.0938 (7)
H7A	0.5346	0.7346	0.3756	0.113*
H7B	0.5361	0.5603	0.3912	0.113*
C8	0.2973 (2)	0.7450 (2)	0.38675 (16)	0.0678 (5)
H8A	0.2448	0.8572	0.3560	0.081*
H8B	0.2883	0.7461	0.4653	0.081*
C9	0.20798 (17)	0.64820 (17)	0.34669 (12)	0.0464 (3)
H9	0.2631 (18)	0.5358 (19)	0.3778 (12)	0.049 (4)*
C10	0.22660 (17)	0.64202 (17)	0.22300 (11)	0.0469 (3)
H10	0.1840 (18)	0.7536 (18)	0.1913 (12)	0.044 (4)*
C11	−0.0042 (2)	0.69508 (18)	0.48589 (11)	0.0510 (4)
O12	0.10751 (17)	0.61613 (15)	0.55101 (9)	0.0701 (4)
C13	−0.1827 (2)	0.7711 (2)	0.52406 (13)	0.0706 (5)
H13A	−0.2376	0.8805	0.4912	0.106*
H13B	−0.1856	0.7740	0.6017	0.106*
H13C	−0.2387	0.7072	0.5036	0.106*
C21	−0.12599 (16)	0.93084 (16)	0.23267 (10)	0.0418 (3)
C22	−0.1697 (2)	0.96372 (19)	0.12409 (12)	0.0609 (4)
H22	−0.1783	0.8833	0.0857	0.073*
C23	−0.2007 (3)	1.1149 (2)	0.07185 (14)	0.0769 (6)
H23	−0.2297	1.1346	−0.0013	0.092*
C24	−0.1894 (2)	1.2356 (2)	0.12555 (14)	0.0684 (5)
H24	−0.2103	1.3368	0.0897	0.082*
C25	−0.1465 (2)	1.20538 (19)	0.23357 (15)	0.0666 (5)
H25	−0.1377	1.2863	0.2712	0.080*
C26	−0.1163 (2)	1.05500 (18)	0.28638 (12)	0.0557 (4)
H26	−0.0889	1.0367	0.3598	0.067*
O41	0.20872 (15)	0.38795 (12)	0.19629 (8)	0.0595 (3)
C42	0.2627 (3)	0.2941 (2)	0.11395 (14)	0.0691 (5)
O43	0.2613 (3)	0.3449 (3)	0.01907 (15)	0.0971 (8)	0.80
O43'	0.1716 (14)	0.3508 (14)	0.0380 (8)	0.0971 (8)	0.20
C44	0.3441 (3)	0.1177 (2)	0.15198 (19)	0.0970 (7)
H44A	0.4143	0.1033	0.2130	0.146*
H44B	0.4103	0.0556	0.0942	0.146*
H44C	0.2601	0.0803	0.1733	0.146*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0459 (6)	0.0479 (6)	0.0344 (5)	−0.0228 (5)	−0.0049 (4)	0.0015 (4)
C2	0.0399 (7)	0.0510 (7)	0.0342 (6)	−0.0212 (6)	−0.0025 (5)	−0.0002 (5)
C3	0.0577 (9)	0.0518 (7)	0.0409 (7)	−0.0310 (7)	−0.0065 (6)	0.0002 (6)
C4	0.0646 (9)	0.0419 (7)	0.0360 (6)	−0.0213 (7)	0.0023 (6)	0.0010 (5)
C5	0.0499 (9)	0.0524 (9)	0.0911 (13)	−0.0146 (7)	0.0146 (8)	0.0035 (8)
C6	0.0470 (10)	0.0703 (12)	0.135 (2)	−0.0235 (9)	0.0116 (11)	0.0057 (12)
C7	0.0511 (11)	0.0884 (14)	0.150 (2)	−0.0373 (10)	−0.0271 (12)	0.0027 (14)
C8	0.0606 (10)	0.0706 (11)	0.0829 (12)	−0.0372 (9)	−0.0167 (9)	−0.0034 (9)
C9	0.0434 (8)	0.0450 (7)	0.0514 (8)	−0.0200 (6)	−0.0096 (6)	0.0047 (6)
C10	0.0436 (8)	0.0407 (7)	0.0520 (8)	−0.0153 (6)	0.0031 (6)	0.0056 (6)
C11	0.0730 (10)	0.0518 (8)	0.0359 (7)	−0.0337 (7)	−0.0046 (7)	−0.0012 (6)
O12	0.0921 (9)	0.0788 (8)	0.0410 (5)	−0.0387 (7)	−0.0189 (6)	0.0094 (5)
C13	0.0854 (13)	0.0840 (12)	0.0442 (8)	−0.0384 (10)	0.0151 (8)	−0.0073 (8)
C21	0.0362 (7)	0.0457 (7)	0.0378 (6)	−0.0120 (5)	−0.0007 (5)	−0.0018 (5)
C22	0.0800 (11)	0.0530 (8)	0.0419 (8)	−0.0199 (8)	−0.0104 (7)	−0.0022 (6)
C23	0.1096 (16)	0.0587 (10)	0.0420 (8)	−0.0171 (10)	−0.0081 (9)	0.0060 (7)
C24	0.0830 (12)	0.0462 (8)	0.0600 (10)	−0.0140 (8)	0.0048 (9)	0.0054 (7)
C25	0.0811 (12)	0.0449 (8)	0.0679 (10)	−0.0208 (8)	−0.0063 (9)	−0.0039 (7)
C26	0.0683 (10)	0.0499 (8)	0.0440 (7)	−0.0199 (7)	−0.0089 (7)	−0.0020 (6)
O41	0.0861 (8)	0.0408 (5)	0.0440 (5)	−0.0199 (5)	0.0030 (5)	−0.0034 (4)
C42	0.0885 (13)	0.0570 (9)	0.0571 (10)	−0.0244 (9)	−0.0011 (9)	−0.0153 (8)
O43	0.144 (2)	0.0827 (10)	0.0456 (10)	−0.0281 (16)	0.0133 (11)	−0.0203 (8)
O43'	0.144 (2)	0.0827 (10)	0.0456 (10)	−0.0281 (16)	0.0133 (11)	−0.0203 (8)
C44	0.125 (2)	0.0529 (10)	0.0951 (16)	−0.0191 (11)	0.0085 (14)	−0.0187 (10)

Geometric parameters (Å, º)

N1—C11	1.3565 (17)	C9—H9	0.974 (15)
N1—C2	1.4707 (16)	C10—H10	0.968 (15)
N1—C9	1.4827 (18)	C11—O12	1.2251 (18)
C2—C3	1.5248 (19)	C11—C13	1.505 (2)
C2—C21	1.5305 (18)	C13—H13A	0.9600
C2—H2	0.9800	C13—H13B	0.9600
C3—C4	1.521 (2)	C13—H13C	0.9600
C3—H3A	0.9700	C21—C22	1.3825 (19)
C3—H3B	0.9700	C21—C26	1.384 (2)
C4—O41	1.4619 (16)	C22—C23	1.384 (2)
C4—C10	1.512 (2)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.363 (3)
C5—C6	1.500 (3)	C23—H23	0.9300
C5—C10	1.529 (2)	C24—C25	1.374 (2)
C5—H5A	0.9700	C24—H24	0.9300
C5—H5B	0.9700	C25—C26	1.381 (2)
C6—C7	1.509 (3)	C25—H25	0.9300
C6—H6A	0.9700	C26—H26	0.9300
C6—H6B	0.9700	O41—C42	1.3192 (19)
C7—C8	1.530 (3)	C42—O43'	1.192 (11)
C7—H7A	0.9700	C42—O43	1.222 (3)
C7—H7B	0.9700	C42—C44	1.488 (3)
C8—C9	1.525 (2)	C44—H44A	0.9600
C8—H8A	0.9700	C44—H44B	0.9600
C8—H8B	0.9700	C44—H44C	0.9600
C9—C10	1.532 (2)
C11—N1—C2	122.98 (12)	N1—C9—H9	109.4 (9)
C11—N1—C9	116.86 (11)	C8—C9—H9	108.4 (9)
C2—N1—C9	117.65 (10)	C10—C9—H9	106.9 (9)
N1—C2—C3	108.01 (11)	C4—C10—C5	113.31 (13)
N1—C2—C21	112.62 (10)	C4—C10—C9	113.20 (11)
C3—C2—C21	116.34 (11)	C5—C10—C9	110.02 (13)
N1—C2—H2	106.4	C4—C10—H10	106.1 (9)
C3—C2—H2	106.4	C5—C10—H10	105.9 (9)
C21—C2—H2	106.4	C9—C10—H10	107.8 (9)
C4—C3—C2	113.17 (11)	O12—C11—N1	121.29 (15)
C4—C3—H3A	108.9	O12—C11—C13	119.91 (14)
C2—C3—H3A	108.9	N1—C11—C13	118.79 (13)
C4—C3—H3B	108.9	C11—C13—H13A	109.5
C2—C3—H3B	108.9	C11—C13—H13B	109.5
H3A—C3—H3B	107.8	H13A—C13—H13B	109.5
O41—C4—C10	108.92 (12)	C11—C13—H13C	109.5
O41—C4—C3	106.92 (11)	H13A—C13—H13C	109.5
C10—C4—C3	112.79 (11)	H13B—C13—H13C	109.5
O41—C4—H4	109.4	C22—C21—C26	117.43 (13)
C10—C4—H4	109.4	C22—C21—C2	121.83 (12)
C3—C4—H4	109.4	C26—C21—C2	120.69 (12)
C6—C5—C10	111.52 (15)	C21—C22—C23	120.70 (15)
C6—C5—H5A	109.3	C21—C22—H22	119.6
C10—C5—H5A	109.3	C23—C22—H22	119.6
C6—C5—H5B	109.3	C24—C23—C22	121.23 (16)
C10—C5—H5B	109.3	C24—C23—H23	119.4
H5A—C5—H5B	108.0	C22—C23—H23	119.4
C5—C6—C7	111.55 (16)	C23—C24—C25	118.93 (15)
C5—C6—H6A	109.3	C23—C24—H24	120.5
C7—C6—H6A	109.3	C25—C24—H24	120.5
C5—C6—H6B	109.3	C24—C25—C26	120.15 (16)
C7—C6—H6B	109.3	C24—C25—H25	119.9
H6A—C6—H6B	108.0	C26—C25—H25	119.9
C6—C7—C8	112.34 (16)	C25—C26—C21	121.56 (14)
C6—C7—H7A	109.1	C25—C26—H26	119.2
C8—C7—H7A	109.1	C21—C26—H26	119.2
C6—C7—H7B	109.1	C42—O41—C4	119.25 (12)
C8—C7—H7B	109.1	O43'—C42—O41	111.0 (5)
H7A—C7—H7B	107.9	O43—C42—O41	124.56 (18)
C7—C8—C9	110.26 (15)	O43'—C42—C44	125.7 (6)
C7—C8—H8A	109.6	O43—C42—C44	123.62 (18)
C9—C8—H8A	109.6	O41—C42—C44	111.45 (16)
C7—C8—H8B	109.6	C42—C44—H44A	109.5
C9—C8—H8B	109.6	C42—C44—H44B	109.5
H8A—C8—H8B	108.1	H44A—C44—H44B	109.5
N1—C9—C8	111.24 (12)	C42—C44—H44C	109.5
N1—C9—C10	111.16 (11)	H44A—C44—H44C	109.5
C8—C9—C10	109.60 (12)	H44B—C44—H44C	109.5
C11—N1—C2—C3	−110.65 (14)	C8—C9—C10—C4	−173.21 (12)
C9—N1—C2—C3	50.78 (14)	N1—C9—C10—C5	−177.74 (11)
C11—N1—C2—C21	119.49 (14)	C8—C9—C10—C5	58.88 (16)
C9—N1—C2—C21	−79.08 (14)	C2—N1—C11—O12	160.51 (13)
N1—C2—C3—C4	−57.53 (13)	C9—N1—C11—O12	−1.06 (19)
C21—C2—C3—C4	70.23 (15)	C2—N1—C11—C13	−21.1 (2)
C2—C3—C4—O41	131.39 (12)	C9—N1—C11—C13	177.35 (13)
C2—C3—C4—C10	11.68 (15)	N1—C2—C21—C22	148.53 (14)
C10—C5—C6—C7	54.7 (2)	C3—C2—C21—C22	23.07 (19)
C5—C6—C7—C8	−53.7 (2)	N1—C2—C21—C26	−33.87 (18)
C6—C7—C8—C9	55.3 (2)	C3—C2—C21—C26	−159.32 (13)
C11—N1—C9—C8	−73.41 (16)	C26—C21—C22—C23	0.6 (3)
C2—N1—C9—C8	124.01 (13)	C2—C21—C22—C23	178.27 (16)
C11—N1—C9—C10	164.15 (12)	C21—C22—C23—C24	−0.1 (3)
C2—N1—C9—C10	1.57 (15)	C22—C23—C24—C25	−0.1 (3)
C7—C8—C9—N1	179.08 (15)	C23—C24—C25—C26	−0.3 (3)
C7—C8—C9—C10	−57.58 (19)	C24—C25—C26—C21	0.9 (3)
O41—C4—C10—C5	49.77 (15)	C22—C21—C26—C25	−1.0 (2)
C3—C4—C10—C5	168.32 (12)	C2—C21—C26—C25	−178.68 (15)
O41—C4—C10—C9	−76.41 (14)	C10—C4—O41—C42	−117.31 (16)
C3—C4—C10—C9	42.14 (15)	C3—C4—O41—C42	120.52 (16)
C6—C5—C10—C4	174.55 (14)	C4—O41—C42—O43'	−34.6 (6)
C6—C5—C10—C9	−57.61 (18)	C4—O41—C42—O43	6.8 (3)
N1—C9—C10—C4	−49.83 (15)	C4—O41—C42—C44	−179.92 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O43^i	0.97	2.59	3.521 (3)	161
C3—H3B···O43′^i	0.97	2.56	3.403 (11)	146
C25—H25···O12^ii	0.93	2.50	3.322 (2)	148
C3—H3A···O12^iii	0.97	2.63	3.5340 (18)	155
C13—H13C···O12^iii	0.96	2.78	3.475 (2)	130

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1.