Phenyl piperidine-1-carboxyl-ate.

In the title compound, C(12)H(15)NO(2), the dihedral angle between the benzene ring and the basal plane of the piperidine ring (which is in a chair conformation) is 49.55 (8)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and very weak C-H⋯π inter-actions.

Related literature

For related structures, see: Shahwar et al. (2009a ▶,b ▶).

Experimental

Crystal data

C12H15NO2

M = 205.25

Monoclinic,

a = 6.2091 (2) Å

b = 7.6881 (3) Å

c = 11.2838 (4) Å

β = 97.211 (2)°

V = 534.39 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.28 × 0.11 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.987, T max = 0.993

6213 measured reflections

1422 independent reflections

1243 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.05

1422 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050958/hb5246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050958/hb5246Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H15NO2	F(000) = 220
Mr = 205.25	Dx = 1.276 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1422 reflections
a = 6.2091 (2) Å	θ = 3.2–28.3°
b = 7.6881 (3) Å	µ = 0.09 mm−1
c = 11.2838 (4) Å	T = 296 K
β = 97.211 (2)°	Needles, colorless
V = 534.39 (3) Å3	0.28 × 0.11 × 0.09 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1422 independent reflections
Radiation source: fine-focus sealed tube	1243 reflections with I > 2σ(I)
graphite	Rint = 0.022
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 3.2°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→10
Tmin = 0.987, Tmax = 0.993	l = −15→14
6213 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.0354P] where P = (Fo2 + 2Fc2)/3
1422 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
O1	−0.00238 (19)	0.6920 (2)	0.32910 (10)	0.0497 (4)
O2	0.3128 (2)	0.83567 (19)	0.31583 (11)	0.0534 (4)
N1	0.2483 (2)	0.7051 (2)	0.48833 (12)	0.0442 (4)
C1	−0.0639 (3)	0.6857 (2)	0.20515 (14)	0.0395 (5)
C2	−0.2721 (3)	0.7369 (3)	0.16604 (16)	0.0465 (6)
C3	−0.3512 (3)	0.7125 (4)	0.04706 (18)	0.0599 (7)
C4	−0.2238 (4)	0.6384 (3)	−0.03033 (18)	0.0631 (8)
C5	−0.0147 (4)	0.5895 (3)	0.01023 (19)	0.0578 (7)
C6	0.0681 (3)	0.6137 (3)	0.12898 (16)	0.0485 (6)
C7	0.2001 (3)	0.7508 (2)	0.37356 (14)	0.0384 (5)
C8	0.1076 (3)	0.6065 (3)	0.55852 (15)	0.0474 (6)
C9	0.0725 (3)	0.7057 (3)	0.67042 (15)	0.0487 (6)
C10	0.2875 (3)	0.7539 (3)	0.74199 (17)	0.0538 (6)
C11	0.4301 (3)	0.8523 (3)	0.66545 (17)	0.0521 (6)
C12	0.4601 (3)	0.7516 (3)	0.55382 (17)	0.0486 (5)
H2	−0.35844	0.78703	0.21843	0.0558*
H3	−0.49220	0.74669	0.01916	0.0719*
H4	−0.27888	0.62132	−0.10998	0.0757*
H5	0.07179	0.53993	−0.04228	0.0693*
H6	0.21007	0.58190	0.15663	0.0582*
H8A	0.17346	0.49472	0.58031	0.0569*
H8B	−0.03120	0.58559	0.51088	0.0569*
H9A	−0.01098	0.63469	0.71919	0.0584*
H9B	−0.00986	0.81054	0.64855	0.0584*
H10A	0.26113	0.82542	0.80952	0.0646*
H10B	0.36158	0.64910	0.77265	0.0646*
H11A	0.36452	0.96411	0.64339	0.0626*
H11B	0.57069	0.87341	0.71114	0.0626*
H12A	0.54102	0.82153	0.50311	0.0584*
H12B	0.54274	0.64671	0.57525	0.0584*

	U11	U22	U33	U12	U13	U23
O1	0.0416 (7)	0.0749 (9)	0.0328 (6)	−0.0111 (7)	0.0056 (5)	0.0005 (7)
O2	0.0542 (7)	0.0587 (8)	0.0497 (7)	−0.0108 (7)	0.0159 (6)	0.0040 (7)
N1	0.0396 (7)	0.0565 (9)	0.0366 (7)	−0.0128 (7)	0.0047 (6)	−0.0020 (7)
C1	0.0429 (9)	0.0422 (9)	0.0336 (8)	−0.0044 (8)	0.0057 (7)	0.0045 (8)
C2	0.0404 (9)	0.0524 (10)	0.0481 (10)	−0.0005 (9)	0.0106 (8)	0.0029 (9)
C3	0.0429 (10)	0.0806 (16)	0.0539 (11)	0.0016 (10)	−0.0034 (8)	0.0127 (12)
C4	0.0619 (13)	0.0892 (18)	0.0366 (10)	−0.0035 (12)	−0.0003 (9)	0.0017 (10)
C5	0.0645 (12)	0.0676 (13)	0.0425 (10)	0.0097 (10)	0.0120 (9)	−0.0034 (9)
C6	0.0469 (10)	0.0573 (11)	0.0415 (9)	0.0120 (9)	0.0068 (8)	0.0056 (9)
C7	0.0368 (8)	0.0406 (8)	0.0395 (8)	−0.0010 (8)	0.0110 (7)	−0.0063 (8)
C8	0.0497 (10)	0.0552 (10)	0.0366 (9)	−0.0162 (9)	0.0027 (7)	0.0026 (8)
C9	0.0488 (9)	0.0599 (12)	0.0376 (9)	−0.0028 (9)	0.0066 (7)	0.0040 (8)
C10	0.0637 (12)	0.0561 (11)	0.0386 (9)	−0.0001 (10)	−0.0054 (8)	−0.0060 (9)
C11	0.0461 (10)	0.0503 (11)	0.0559 (11)	−0.0050 (9)	−0.0096 (8)	−0.0079 (9)
C12	0.0360 (8)	0.0536 (10)	0.0549 (10)	−0.0043 (8)	0.0002 (7)	−0.0031 (9)

O1—C1	1.4037 (19)	C2—H2	0.9300
O1—C7	1.371 (2)	C3—H3	0.9300
O2—C7	1.206 (2)	C4—H4	0.9300
N1—C7	1.339 (2)	C5—H5	0.9300
N1—C8	1.463 (2)	C6—H6	0.9300
N1—C12	1.470 (2)	C8—H8A	0.9700
C1—C2	1.370 (3)	C8—H8B	0.9700
C1—C6	1.376 (3)	C9—H9A	0.9700
C2—C3	1.383 (3)	C9—H9B	0.9700
C3—C4	1.373 (3)	C10—H10A	0.9700
C4—C5	1.374 (3)	C10—H10B	0.9700
C5—C6	1.386 (3)	C11—H11A	0.9700
C8—C9	1.514 (3)	C11—H11B	0.9700
C9—C10	1.517 (3)	C12—H12A	0.9700
C10—C11	1.515 (3)	C12—H12B	0.9700
C11—C12	1.510 (3)
C1—O1—C7	119.90 (13)	C1—C6—H6	121.00
C7—N1—C8	125.71 (14)	C5—C6—H6	121.00
C7—N1—C12	119.99 (15)	N1—C8—H8A	110.00
C8—N1—C12	114.30 (14)	N1—C8—H8B	110.00
O1—C1—C2	116.02 (15)	C9—C8—H8A	110.00
O1—C1—C6	121.82 (16)	C9—C8—H8B	110.00
C2—C1—C6	121.75 (16)	H8A—C8—H8B	108.00
C1—C2—C3	118.64 (18)	C8—C9—H9A	109.00
C2—C3—C4	120.71 (19)	C8—C9—H9B	109.00
C3—C4—C5	119.83 (19)	C10—C9—H9A	109.00
C4—C5—C6	120.4 (2)	C10—C9—H9B	109.00
C1—C6—C5	118.69 (18)	H9A—C9—H9B	108.00
O1—C7—O2	123.27 (15)	C9—C10—H10A	109.00
O1—C7—N1	110.54 (14)	C9—C10—H10B	109.00
O2—C7—N1	126.16 (16)	C11—C10—H10A	109.00
N1—C8—C9	110.42 (17)	C11—C10—H10B	109.00
C8—C9—C10	110.97 (16)	H10A—C10—H10B	108.00
C9—C10—C11	110.91 (16)	C10—C11—H11A	109.00
C10—C11—C12	111.21 (18)	C10—C11—H11B	109.00
N1—C12—C11	110.36 (15)	C12—C11—H11A	109.00
C1—C2—H2	121.00	C12—C11—H11B	109.00
C3—C2—H2	121.00	H11A—C11—H11B	108.00
C2—C3—H3	120.00	N1—C12—H12A	110.00
C4—C3—H3	120.00	N1—C12—H12B	110.00
C3—C4—H4	120.00	C11—C12—H12A	110.00
C5—C4—H4	120.00	C11—C12—H12B	110.00
C4—C5—H5	120.00	H12A—C12—H12B	108.00
C6—C5—H5	120.00
C7—O1—C1—C2	−139.17 (18)	O1—C1—C2—C3	−171.8 (2)
C7—O1—C1—C6	48.0 (2)	C6—C1—C2—C3	1.0 (3)
C1—O1—C7—O2	18.0 (3)	O1—C1—C6—C5	171.01 (18)
C1—O1—C7—N1	−163.81 (15)	C2—C1—C6—C5	−1.4 (3)
C8—N1—C7—O1	−0.1 (2)	C1—C2—C3—C4	0.0 (4)
C8—N1—C7—O2	178.06 (18)	C2—C3—C4—C5	−0.7 (4)
C12—N1—C7—O1	178.78 (15)	C3—C4—C5—C6	0.3 (4)
C12—N1—C7—O2	−3.1 (3)	C4—C5—C6—C1	0.7 (3)
C7—N1—C8—C9	−124.65 (18)	N1—C8—C9—C10	−54.5 (2)
C12—N1—C8—C9	56.5 (2)	C8—C9—C10—C11	54.4 (2)
C7—N1—C12—C11	124.72 (18)	C9—C10—C11—C12	−54.5 (2)
C8—N1—C12—C11	−56.3 (2)	C10—C11—C12—N1	54.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.93	2.47	3.342 (2)	157
C5—H5···Cg2ii	0.93	2.99	3.632 (2)	128
C10—H10A···Cg2iii	0.97	2.97	3.848 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.93	2.47	3.342 (2)	157
C5—H5⋯Cg2ii	0.93	2.99	3.632 (2)	128
C10—H10A⋯Cg2iii	0.97	2.97	3.848 (2)	151

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the C1–C6 ring.