Methyl 4-(piperidin-1-ylcarbon-yl)benzoate.

In the title compound, C(14)H(17)NO(3), the piperidine ring has a chair conformation and an intra-molecular C-H⋯O inter-action stabilizes the mol-ecular conformation. In the crystal, weak inter-molecular C-H⋯O inter-actions occur.

Related literature

For Pd(0)-catalysed carbonyl­ation of aryl halides, see: Jia & Morris (1991 ▶); Stille & Wong (1975 ▶); Magerlein, et al. (2001 ▶); Zhao et al. (2008 ▶). For procedural modifications for carbonyl­ation reactions, see: Lagerlund & Larhed (2006 ▶). For the preparation of other piperidine derivatives, see Lima et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H17NO3

M = 247.29

Triclinic,

a = 5.879 (5) Å

b = 9.693 (5) Å

c = 12.190 (5) Å

α = 69.684 (5)°

β = 82.535 (5)°

γ = 77.502 (5)°

V = 634.9 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.05 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer

4958 measured reflections

2958 independent reflections

2036 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.122

S = 1.01

2958 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021720/zs2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021720/zs2043Isup2.hkl

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

C14H17NO3	Z = 2
Mr = 247.29	F(000) = 264
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.879 (5) Å	Cell parameters from 2414 reflections
b = 9.693 (5) Å	θ = 3.3–29.4°
c = 12.190 (5) Å	µ = 0.09 mm−1
α = 69.684 (5)°	T = 150 K
β = 82.535 (5)°	Prism, colourless
γ = 77.502 (5)°	0.05 × 0.05 × 0.05 mm
V = 634.9 (7) Å3

Oxford Diffraction Xcalibur Atlas Gemini Ultra diffractometer	Rint = 0.033
Detector resolution: 10.4186 pixels mm-1	θmax = 29.4°, θmin = 3.3°
ω scans	h = −7→7
4958 measured reflections	k = −11→12
2958 independent reflections	l = −13→16
2036 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044	w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.25 e Å−3
2958 reflections	Δρmin = −0.26 e Å−3
164 parameters

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.

	x	y	z	Uiso*/Ueq
O3	0.73762 (16)	0.78416 (10)	0.51830 (8)	0.0285 (2)
O2	1.10549 (18)	0.65801 (11)	0.54066 (9)	0.0377 (3)
O1	1.41852 (17)	1.30674 (12)	0.11938 (9)	0.0378 (3)
N1	1.14709 (19)	1.30851 (12)	0.00274 (9)	0.0232 (3)
C7	1.1642 (2)	1.13450 (14)	0.20582 (11)	0.0214 (3)
C11	0.8703 (2)	1.03005 (14)	0.34869 (11)	0.0220 (3)
H11	0.7179	1.0388	0.3812	0.026*
C10	1.0327 (2)	0.90031 (14)	0.39573 (11)	0.0211 (3)
C13	0.9679 (2)	0.76837 (15)	0.49291 (11)	0.0240 (3)
C4	1.3404 (3)	1.36011 (16)	−0.19405 (12)	0.0285 (3)
H4A	1.4773	1.2843	−0.167	0.034*
H4B	1.389	1.439	−0.2616	0.034*
C8	1.3275 (2)	1.00679 (15)	0.25594 (12)	0.0256 (3)
H8	1.482	1	0.2262	0.031*
C12	0.9354 (2)	1.14597 (14)	0.25349 (11)	0.0234 (3)
H12	0.8259	1.2316	0.2214	0.028*
C5	1.2352 (3)	1.42408 (15)	−0.09739 (12)	0.0281 (3)
H5A	1.3527	1.4615	−0.0725	0.034*
H5B	1.1085	1.5071	−0.1269	0.034*
C3	1.1643 (3)	1.29141 (15)	−0.22919 (12)	0.0275 (3)
H3A	1.2388	1.2434	−0.2858	0.033*
H3B	1.0372	1.3697	−0.266	0.033*
C2	1.0677 (2)	1.17679 (15)	−0.12294 (11)	0.0260 (3)
H2A	0.9453	1.1417	−0.1463	0.031*
H2B	1.1909	1.0915	−0.093	0.031*
C6	1.2522 (2)	1.25752 (15)	0.10503 (12)	0.0233 (3)
C9	1.2617 (2)	0.89002 (15)	0.34957 (12)	0.0259 (3)
H9	1.3711	0.8044	0.3817	0.031*
C1	0.9701 (2)	1.24338 (16)	−0.02665 (12)	0.0258 (3)
H1A	0.8338	1.3201	−0.0527	0.031*
H1B	0.9226	1.1659	0.0424	0.031*
C14	0.6585 (3)	0.65522 (17)	0.60534 (13)	0.0328 (3)
H14A	0.7227	0.5674	0.5842	0.049*
H14B	0.4912	0.6707	0.6088	0.049*
H14C	0.7094	0.6423	0.6806	0.049*

	U11	U22	U33	U12	U13	U23
O3	0.0247 (5)	0.0288 (5)	0.0255 (5)	−0.0082 (4)	0.0020 (4)	−0.0002 (4)
O2	0.0287 (6)	0.0328 (6)	0.0408 (6)	−0.0048 (5)	−0.0073 (5)	0.0027 (5)
O1	0.0341 (6)	0.0479 (6)	0.0359 (6)	−0.0257 (5)	−0.0023 (5)	−0.0085 (5)
N1	0.0275 (6)	0.0235 (6)	0.0219 (6)	−0.0127 (5)	0.0033 (4)	−0.0085 (5)
C7	0.0230 (7)	0.0256 (6)	0.0204 (7)	−0.0095 (5)	0.0002 (5)	−0.0110 (5)
C11	0.0180 (7)	0.0274 (7)	0.0226 (7)	−0.0067 (5)	0.0020 (5)	−0.0102 (6)
C10	0.0228 (7)	0.0254 (7)	0.0184 (6)	−0.0077 (5)	−0.0025 (5)	−0.0088 (5)
C13	0.0234 (7)	0.0286 (7)	0.0215 (7)	−0.0067 (6)	−0.0033 (5)	−0.0083 (6)
C4	0.0320 (8)	0.0276 (7)	0.0240 (7)	−0.0118 (6)	0.0052 (6)	−0.0050 (6)
C8	0.0175 (7)	0.0344 (7)	0.0260 (7)	−0.0073 (6)	0.0012 (5)	−0.0108 (6)
C12	0.0216 (7)	0.0233 (7)	0.0260 (7)	−0.0030 (5)	−0.0020 (5)	−0.0095 (6)
C5	0.0356 (8)	0.0213 (7)	0.0279 (7)	−0.0126 (6)	0.0033 (6)	−0.0064 (6)
C3	0.0311 (8)	0.0294 (7)	0.0221 (7)	−0.0055 (6)	−0.0010 (5)	−0.0090 (6)
C2	0.0286 (8)	0.0279 (7)	0.0251 (7)	−0.0089 (6)	−0.0044 (6)	−0.0099 (6)
C6	0.0214 (7)	0.0252 (7)	0.0259 (7)	−0.0077 (5)	0.0034 (5)	−0.0113 (6)
C9	0.0221 (7)	0.0291 (7)	0.0257 (7)	−0.0020 (6)	−0.0053 (5)	−0.0083 (6)
C1	0.0235 (7)	0.0308 (7)	0.0250 (7)	−0.0103 (6)	−0.0004 (5)	−0.0087 (6)
C14	0.0298 (8)	0.0348 (8)	0.0278 (8)	−0.0132 (6)	0.0000 (6)	0.0008 (6)

O3—C13	1.337 (2)	C4—H4B	0.97
O3—C14	1.4514 (17)	C8—C9	1.3826 (19)
O2—C13	1.2054 (17)	C8—H8	0.93
O1—C6	1.2320 (18)	C12—H12	0.93
N1—C6	1.3496 (18)	C5—H5A	0.97
N1—C1	1.4655 (19)	C5—H5B	0.97
N1—C5	1.4664 (17)	C3—C2	1.5223 (19)
C7—C12	1.391 (2)	C3—H3A	0.97
C7—C8	1.393 (2)	C3—H3B	0.97
C7—C6	1.5113 (18)	C2—C1	1.5213 (19)
C11—C12	1.3861 (18)	C2—H2A	0.97
C11—C10	1.3942 (19)	C2—H2B	0.97
C11—H11	0.93	C9—H9	0.93
C10—C9	1.387 (2)	C1—H1A	0.97
C10—C13	1.4918 (19)	C1—H1B	0.97
C4—C5	1.5191 (19)	C14—H14A	0.96
C4—C3	1.520 (2)	C14—H14B	0.96
C4—H4A	0.97	C14—H14C	0.96
C13—O3—C14	115.47 (10)	C4—C5—H5B	109.6
C6—N1—C1	125.92 (11)	H5A—C5—H5B	108.1
C6—N1—C5	119.70 (12)	C4—C3—C2	110.94 (12)
C1—N1—C5	113.67 (11)	C4—C3—H3A	109.5
C12—C7—C8	119.40 (12)	C2—C3—H3A	109.5
C12—C7—C6	123.66 (11)	C4—C3—H3B	109.5
C8—C7—C6	116.86 (12)	C2—C3—H3B	109.5
C12—C11—C10	120.13 (12)	H3A—C3—H3B	108
C12—C11—H11	119.9	C1—C2—C3	111.32 (11)
C10—C11—H11	119.9	C1—C2—H2A	109.4
C9—C10—C11	119.69 (12)	C3—C2—H2A	109.4
C9—C10—C13	118.03 (11)	C1—C2—H2B	109.4
C11—C10—C13	122.26 (12)	C3—C2—H2B	109.4
O2—C13—O3	123.63 (13)	H2A—C2—H2B	108
O2—C13—C10	124.22 (13)	O1—C6—N1	122.56 (12)
O3—C13—C10	112.10 (11)	O1—C6—C7	118.58 (12)
C5—C4—C3	110.68 (12)	N1—C6—C7	118.86 (12)
C5—C4—H4A	109.5	C8—C9—C10	120.14 (12)
C3—C4—H4A	109.5	C8—C9—H9	119.9
C5—C4—H4B	109.5	C10—C9—H9	119.9
C3—C4—H4B	109.5	N1—C1—C2	110.13 (12)
H4A—C4—H4B	108.1	N1—C1—H1A	109.6
C9—C8—C7	120.44 (13)	C2—C1—H1A	109.6
C9—C8—H8	119.8	N1—C1—H1B	109.6
C7—C8—H8	119.8	C2—C1—H1B	109.6
C11—C12—C7	120.15 (12)	H1A—C1—H1B	108.1
C11—C12—H12	119.9	O3—C14—H14A	109.5
C7—C12—H12	119.9	O3—C14—H14B	109.5
N1—C5—C4	110.27 (11)	H14A—C14—H14B	109.5
N1—C5—H5A	109.6	O3—C14—H14C	109.5
C4—C5—H5A	109.6	H14A—C14—H14C	109.5
N1—C5—H5B	109.6	H14B—C14—H14C	109.5
C12—C11—C10—C9	2.35 (19)	C5—C4—C3—C2	−54.04 (15)
C12—C11—C10—C13	−175.86 (12)	C4—C3—C2—C1	53.59 (15)
C14—O3—C13—O2	−2.60 (19)	C1—N1—C6—O1	171.43 (13)
C14—O3—C13—C10	175.10 (11)	C5—N1—C6—O1	1.71 (19)
C9—C10—C13—O2	6.5 (2)	C1—N1—C6—C7	−8.12 (19)
C11—C10—C13—O2	−175.28 (13)	C5—N1—C6—C7	−177.84 (11)
C9—C10—C13—O3	−171.20 (11)	C12—C7—C6—O1	122.57 (15)
C11—C10—C13—O3	7.03 (18)	C8—C7—C6—O1	−54.07 (17)
C12—C7—C8—C9	2.31 (19)	C12—C7—C6—N1	−57.86 (18)
C6—C7—C8—C9	179.10 (12)	C8—C7—C6—N1	125.50 (14)
C10—C11—C12—C7	−1.17 (19)	C7—C8—C9—C10	−1.1 (2)
C8—C7—C12—C11	−1.15 (19)	C11—C10—C9—C8	−1.19 (19)
C6—C7—C12—C11	−177.71 (12)	C13—C10—C9—C8	177.09 (12)
C6—N1—C5—C4	112.46 (14)	C6—N1—C1—C2	−112.70 (14)
C1—N1—C5—C4	−58.47 (15)	C5—N1—C1—C2	57.56 (15)
C3—C4—C5—N1	55.55 (15)	C3—C2—C1—N1	−54.21 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1	0.97	2.33	2.750 (3)	105
C14—H14B···O2i	0.96	2.56	3.436 (4)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1	0.97	2.33	2.750 (3)	105
C14—H14B⋯O2i	0.96	2.56	3.436 (4)	153

Symmetry code: (i) .