Methyl 4-oxo-r-2,c-6-di­phenyl­piperidine-3-carboxyl­ate

The crystal structure of the title compound, C₁₉H₁₉NO₃, was determined because it is believed to possess medicinal properties. The piperidine ring assumes a chair conformation. The benzene-ring and methoxy­carbonyl substituents are oriented equatorially. Whereas C—H...O intermolecular hydrogen bonds stabilize the crystal packing, the NH group does not form any hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.136
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?
PLAT707_ALERT_1_C D...A   Calc  3.3834(19), Rep    3.386(2), Dev..       1.37 Sigma
              C8   -O2      1.555   3.756

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

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

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Computing details

Data collection: SMART (Siemens, 2000); cell refinement: SAINT (Siemens, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1998) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Methyl 4-oxo-r-2,c-6-diphenylpiperidine-3-carboxylate

Crystal data

C19H19NO3	F(000) = 656
Mr = 309.35	Dx = 1.226 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7563 (13) Å	Cell parameters from 3296 reflections
b = 7.710 (1) Å	θ = 1.8–26.0°
c = 22.810 (3) Å	µ = 0.08 mm^−1
β = 102.348 (4)°	T = 293 K
V = 1676.1 (4) Å^3	Block, pale yellow
Z = 4	0.41 × 0.20 × 0.12 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.077
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
ω scans	h = −12→12
12559 measured reflections	k = −8→9
3296 independent reflections	l = −28→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 0.137P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3296 reflections	Δρmax = 0.17 e Å^−3
213 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

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
N1	0.71975 (11)	0.18726 (15)	0.55272 (4)	0.0517 (3)
H1	0.6560 (16)	0.116 (2)	0.5644 (6)	0.066 (4)*
C6	0.71963 (13)	0.15034 (17)	0.48980 (5)	0.0514 (3)
H6	0.7517	0.0312	0.4861	0.062*
C7	0.57575 (13)	0.17356 (16)	0.45010 (5)	0.0508 (3)
C8	0.54901 (15)	0.1069 (2)	0.39227 (6)	0.0631 (4)
H8	0.6176	0.0419	0.3796	0.076*
C9	0.42225 (17)	0.1355 (2)	0.35339 (7)	0.0731 (4)
H9	0.4063	0.0907	0.3147	0.088*
C10	0.31945 (16)	0.2298 (2)	0.37138 (8)	0.0742 (5)
H10	0.2341	0.2497	0.3450	0.089*
C11	0.34365 (17)	0.2944 (2)	0.42868 (8)	0.0751 (5)
H11	0.2738	0.3571	0.4413	0.090*
C12	0.47070 (15)	0.26719 (19)	0.46768 (7)	0.0624 (4)
H12	0.4859	0.3124	0.5063	0.075*
C2	0.85514 (13)	0.15684 (17)	0.59352 (5)	0.0503 (3)
H2	0.8849	0.0371	0.5889	0.060*
C13	0.84070 (14)	0.18508 (17)	0.65771 (5)	0.0538 (3)
C14	0.75181 (17)	0.3099 (2)	0.67176 (6)	0.0655 (4)
H14	0.6995	0.3779	0.6414	0.079*
C15	0.7394 (2)	0.3353 (3)	0.73052 (7)	0.0860 (5)
H15	0.6786	0.4194	0.7394	0.103*
C16	0.8168 (2)	0.2360 (3)	0.77546 (7)	0.0920 (6)
H16	0.8082	0.2520	0.8149	0.110*
C17	0.9063 (2)	0.1141 (3)	0.76232 (7)	0.0894 (6)
H17	0.9595	0.0479	0.7930	0.107*
C3	0.96430 (13)	0.28280 (18)	0.57697 (5)	0.0520 (3)
H3	0.9393	0.4011	0.5865	0.062*
C18	0.91886 (16)	0.0875 (2)	0.70368 (6)	0.0703 (4)
H18	0.9803	0.0036	0.6952	0.084*
C4	0.96309 (15)	0.2740 (2)	0.51030 (6)	0.0614 (4)
C5	0.82156 (15)	0.2770 (2)	0.46995 (6)	0.0637 (4)
H5A	0.8302	0.2478	0.4295	0.076*
H5B	0.7836	0.3935	0.4691	0.076*
C19	1.11106 (15)	0.24618 (19)	0.61132 (6)	0.0588 (4)
C20	1.33186 (19)	0.3722 (3)	0.65082 (11)	0.1084 (7)
H20A	1.3747	0.4845	0.6578	0.163*
H20B	1.3772	0.3071	0.6245	0.163*
H20C	1.3415	0.3118	0.6883	0.163*
O1	1.07038 (12)	0.2678 (2)	0.49241 (5)	0.0937 (4)
O2	1.15769 (11)	0.10441 (15)	0.62429 (5)	0.0829 (4)
O3	1.18499 (10)	0.39191 (14)	0.62358 (5)	0.0740 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0527 (6)	0.0596 (7)	0.0465 (6)	−0.0002 (5)	0.0187 (5)	0.0034 (5)
C6	0.0565 (7)	0.0528 (7)	0.0480 (6)	0.0037 (5)	0.0184 (5)	−0.0011 (5)
C7	0.0557 (7)	0.0470 (7)	0.0525 (7)	−0.0007 (5)	0.0180 (6)	0.0043 (5)
C8	0.0640 (8)	0.0674 (9)	0.0588 (8)	0.0033 (7)	0.0153 (6)	−0.0054 (6)
C9	0.0754 (10)	0.0768 (10)	0.0625 (8)	−0.0046 (8)	0.0042 (7)	−0.0013 (7)
C10	0.0619 (9)	0.0711 (10)	0.0836 (11)	0.0003 (7)	0.0020 (8)	0.0150 (8)
C11	0.0636 (9)	0.0729 (10)	0.0919 (11)	0.0162 (8)	0.0239 (8)	0.0104 (8)
C12	0.0652 (8)	0.0632 (9)	0.0622 (8)	0.0094 (6)	0.0212 (7)	0.0021 (6)
C2	0.0553 (7)	0.0482 (7)	0.0500 (7)	0.0036 (5)	0.0173 (5)	0.0029 (5)
C13	0.0602 (8)	0.0546 (7)	0.0485 (7)	−0.0057 (6)	0.0159 (6)	0.0045 (5)
C14	0.0817 (10)	0.0648 (9)	0.0542 (7)	0.0023 (7)	0.0237 (7)	0.0009 (6)
C15	0.1118 (14)	0.0887 (12)	0.0674 (10)	−0.0075 (10)	0.0415 (10)	−0.0153 (8)
C16	0.1178 (15)	0.1143 (16)	0.0483 (8)	−0.0308 (13)	0.0277 (9)	−0.0045 (9)
C17	0.1004 (13)	0.1101 (15)	0.0528 (8)	−0.0153 (11)	0.0056 (8)	0.0214 (9)
C3	0.0528 (7)	0.0534 (7)	0.0527 (7)	0.0021 (5)	0.0180 (5)	0.0003 (5)
C18	0.0706 (9)	0.0777 (10)	0.0611 (8)	−0.0015 (8)	0.0106 (7)	0.0151 (7)
C4	0.0603 (8)	0.0726 (9)	0.0571 (8)	−0.0082 (7)	0.0256 (6)	−0.0020 (6)
C5	0.0639 (8)	0.0850 (10)	0.0463 (7)	−0.0085 (7)	0.0208 (6)	0.0041 (6)
C19	0.0569 (8)	0.0641 (9)	0.0587 (8)	0.0049 (6)	0.0196 (6)	−0.0007 (6)
C20	0.0664 (11)	0.1096 (16)	0.1336 (17)	−0.0018 (10)	−0.0131 (10)	−0.0165 (13)
O1	0.0642 (7)	0.1559 (13)	0.0700 (7)	−0.0146 (7)	0.0345 (6)	−0.0128 (7)
O2	0.0625 (6)	0.0715 (7)	0.1151 (9)	0.0134 (5)	0.0199 (6)	0.0120 (6)
O3	0.0621 (6)	0.0721 (7)	0.0814 (7)	−0.0019 (5)	0.0012 (5)	−0.0092 (5)

Geometric parameters (Å, º)

N1—C6	1.4628 (15)	C14—C15	1.385 (2)
N1—C2	1.4631 (17)	C14—H14	0.9300
N1—H1	0.914 (16)	C15—C16	1.370 (3)
C6—C7	1.5096 (18)	C15—H15	0.9300
C6—C5	1.5300 (19)	C16—C17	1.359 (3)
C6—H6	0.9800	C16—H16	0.9300
C7—C12	1.3813 (19)	C17—C18	1.384 (2)
C7—C8	1.3877 (18)	C17—H17	0.9300
C8—C9	1.377 (2)	C3—C19	1.5047 (19)
C8—H8	0.9300	C3—C4	1.5199 (18)
C9—C10	1.371 (2)	C3—H3	0.9800
C9—H9	0.9300	C18—H18	0.9300
C10—C11	1.371 (2)	C4—O1	1.2030 (17)
C10—H10	0.9300	C4—C5	1.487 (2)
C11—C12	1.379 (2)	C5—H5A	0.9700
C11—H11	0.9300	C5—H5B	0.9700
C12—H12	0.9300	C19—O2	1.1965 (17)
C2—C13	1.5163 (17)	C19—O3	1.3321 (17)
C2—C3	1.5466 (18)	C20—O3	1.443 (2)
C2—H2	0.9800	C20—H20A	0.9600
C13—C14	1.378 (2)	C20—H20B	0.9600
C13—C18	1.3801 (19)	C20—H20C	0.9600
C6—N1—C2	113.84 (10)	C15—C14—H14	119.6
C6—N1—H1	108.1 (9)	C16—C15—C14	119.79 (18)
C2—N1—H1	107.2 (9)	C16—C15—H15	120.1
N1—C6—C7	111.78 (10)	C14—C15—H15	120.1
N1—C6—C5	107.57 (11)	C17—C16—C15	119.92 (16)
C7—C6—C5	109.06 (10)	C17—C16—H16	120.0
N1—C6—H6	109.5	C15—C16—H16	120.0
C7—C6—H6	109.5	C16—C17—C18	120.62 (16)
C5—C6—H6	109.5	C16—C17—H17	119.7
C12—C7—C8	117.98 (13)	C18—C17—H17	119.7
C12—C7—C6	122.71 (11)	C19—C3—C4	108.41 (11)
C8—C7—C6	119.21 (12)	C19—C3—C2	112.54 (10)
C9—C8—C7	120.88 (14)	C4—C3—C2	110.98 (11)
C9—C8—H8	119.6	C19—C3—H3	108.3
C7—C8—H8	119.6	C4—C3—H3	108.3
C10—C9—C8	120.42 (15)	C2—C3—H3	108.3
C10—C9—H9	119.8	C13—C18—C17	120.31 (17)
C8—C9—H9	119.8	C13—C18—H18	119.8
C9—C10—C11	119.35 (14)	C17—C18—H18	119.8
C9—C10—H10	120.3	O1—C4—C5	123.43 (12)
C11—C10—H10	120.3	O1—C4—C3	121.33 (13)
C10—C11—C12	120.50 (15)	C5—C4—C3	115.23 (12)
C10—C11—H11	119.8	C4—C5—C6	112.54 (11)
C12—C11—H11	119.8	C4—C5—H5A	109.1
C11—C12—C7	120.86 (14)	C6—C5—H5A	109.1
C11—C12—H12	119.6	C4—C5—H5B	109.1
C7—C12—H12	119.6	C6—C5—H5B	109.1
N1—C2—C13	109.49 (10)	H5A—C5—H5B	107.8
N1—C2—C3	108.61 (10)	O2—C19—O3	123.95 (14)
C13—C2—C3	110.89 (10)	O2—C19—C3	124.70 (13)
N1—C2—H2	109.3	O3—C19—C3	111.30 (11)
C13—C2—H2	109.3	O3—C20—H20A	109.5
C3—C2—H2	109.3	O3—C20—H20B	109.5
C14—C13—C18	118.47 (13)	H20A—C20—H20B	109.5
C14—C13—C2	121.19 (11)	O3—C20—H20C	109.5
C18—C13—C2	120.33 (13)	H20A—C20—H20C	109.5
C13—C14—C15	120.89 (15)	H20B—C20—H20C	109.5
C13—C14—H14	119.6	C19—O3—C20	116.41 (13)
C2—N1—C6—C7	176.64 (10)	C14—C15—C16—C17	0.5 (3)
C2—N1—C6—C5	−63.66 (14)	C15—C16—C17—C18	−0.8 (3)
N1—C6—C7—C12	18.28 (17)	N1—C2—C3—C19	−172.71 (10)
C5—C6—C7—C12	−100.54 (14)	C13—C2—C3—C19	66.93 (14)
N1—C6—C7—C8	−165.37 (12)	N1—C2—C3—C4	−51.02 (14)
C5—C6—C7—C8	75.81 (15)	C13—C2—C3—C4	−171.38 (11)
C12—C7—C8—C9	0.9 (2)	C14—C13—C18—C17	0.7 (2)
C6—C7—C8—C9	−175.57 (13)	C2—C13—C18—C17	179.61 (14)
C7—C8—C9—C10	−0.5 (2)	C16—C17—C18—C13	0.1 (3)
C8—C9—C10—C11	−0.4 (2)	C19—C3—C4—O1	−11.1 (2)
C9—C10—C11—C12	0.9 (2)	C2—C3—C4—O1	−135.20 (16)
C10—C11—C12—C7	−0.4 (2)	C19—C3—C4—C5	169.90 (12)
C8—C7—C12—C11	−0.5 (2)	C2—C3—C4—C5	45.82 (16)
C6—C7—C12—C11	175.90 (13)	O1—C4—C5—C6	133.58 (17)
C6—N1—C2—C13	−175.53 (10)	C3—C4—C5—C6	−47.47 (17)
C6—N1—C2—C3	63.25 (14)	N1—C6—C5—C4	53.33 (15)
N1—C2—C13—C14	−34.55 (17)	C7—C6—C5—C4	174.75 (11)
C3—C2—C13—C14	85.28 (15)	C4—C3—C19—O2	−86.19 (17)
N1—C2—C13—C18	146.60 (13)	C2—C3—C19—O2	36.94 (19)
C3—C2—C13—C18	−93.57 (15)	C4—C3—C19—O3	91.35 (13)
C18—C13—C14—C15	−1.0 (2)	C2—C3—C19—O3	−145.52 (11)
C2—C13—C14—C15	−179.85 (14)	O2—C19—O3—C20	3.9 (2)
C13—C14—C15—C16	0.4 (3)	C3—C19—O3—C20	−173.64 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2^i	0.93	2.49	3.386 (2)	163

Symmetry code: (i) −x+2, −y, −z+1.