N-[(1-Benzoyl­piperidin-4-yl)meth­yl]benzamide

Prathebha, K.; Reuben Jonathan, D.; Shanmugam, S.; Usha, G.

doi:10.1107/S1600536814012793

N-[(1-Benzoylpiperidin-4-yl)methyl]benzamide

K. Prathebha, D. Reuben Jonathan, S. Shanmugam and G. Usha

In the title compound, C₂₀H₂₂N₂O₂, the piperidine ring adopts a chair conformation. The phenyl rings are inclined to one another by 80.1 (1)° and make dihedral angles of 46.1 (1) and 40.2 (1)° with the mean plane of the piperidine ring. In the crystal, pairs of N—H

O hydrogen bonds link the molecules into inversion dimers. C—H

O interactions further link the molecules, forming a three-dimensional supramolecular network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814012793/bt6968sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814012793/bt6968Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814012793/bt6968Isup3.cml Supplementary material

CCDC reference: 987515

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.043
wR factor = 0.125
Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.60 Why ?
PLAT411_ALERT_2_C Short Inter H...H Contact  H5     ..  H5      ..       2.08 Ang.

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Why ?
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         29 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   4 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Biologically active alkaloids of substituted piperidines have been targeted for their total or partial synthesis (Ramalingan et al., 2004). Piperidines are known to have CNS depressant action at low dosage levels and stimulant activity with increased doses. In addition, the nucleus also possesses analgesic, anglionic blocking and anesthetic properties as well (Sergeant & May, 1970). We report in this communication, the synthesis and crystal structure of a new piperidine derivative.

The phenyl rings form dihedral angles of 46.1 (1)° and 40.2 (1)°, respectively, with the best plane through the piperidine ring atoms. The C—N distances [1.337 (2)- 1.468 (2) Å] are in the normal range and are in good agreement with values of a similar reported structure (Ávila et al., 2010). The piperdine ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) of q2 = 0.0351 (1) Å, phi2 = -50.61 (3)° q3 = 0.5633 (1) Å, QT = 0.5644 (2) Å and θ2 = 3.67 (2)°.

The crystal packing shows N-H···O hydrogen bonds linking the molecules to centrosymmetric dimers (Fig. 2).

Related literature top

For the synthesis of the title compound, see: Prathebha et al. (2013); Venkatraj et al. (2008). For the biological activity of piperdine derivatives, see: Ramalingan et al. (2004); Sergeant & May (1970). For bond-length data, see: Allen et al. (1987). For related structures, see: Al-abbasi et al. (2010); Ávila et al. (2010). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The procedure (Prathebha et al., 2013, Venkatraj et al., 2008) adopted in the synthesis of the typical diamide is as follows: In a 250 mL round-bottomed flask 4-methyl piperidine (0.01 mol) was taken in, to which 100 mL of ethyl methyl ketone was added and stirred at room temperature. After 5 minutes, triethylamine (0.02 mol) was added and the mixture was stirred for 15 minutes. Then, benzoyl chloride (0.02 mol) was added and the reaction mixture was stirred at room temperature for about 2 h. A white precipitate of triethyl ammonium chloride was formed. It was filtered and the filterate was evaporated to get the crude product. The crude product was recrystallized twice from ethyl methyl ketone. Melting Point: 127 °C, yield: 85%.

Structure description top

The crystal packing shows N-H···O hydrogen bonds linking the molecules to centrosymmetric dimers (Fig. 2).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds.
	Fig. 3. Experimental procedure

N-[(1-Benzoylpiperidin-4-yl)methyl]benzamide top

Crystal data top

C₂₀H₂₂N₂O₂	Z = 2
M_r = 322.40	F(000) = 344
Triclinic, P1	D_x = 1.244 Mg m⁻³ D_m = 1.188 Mg m⁻³ D_m measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8039 (2) Å	Cell parameters from 3562 reflections
b = 10.4453 (2) Å	θ = 2.3–26.5°
c = 10.6765 (2) Å	µ = 0.08 mm⁻¹
α = 62.208 (1)°	T = 293 K
β = 66.009 (1)°	Block, colourless
γ = 68.150 (1)°	0.22 × 0.20 × 0.20 mm
V = 860.80 (3) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3562 independent reflections
Radiation source: fine-focus sealed tube	2929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and φ scan	θ_max = 26.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.982, T_max = 0.984	k = −13→13
12912 measured reflections	l = −13→13

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0625P)² + 0.1352P] where P = (F_o² + 2F_c²)/3
3531 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O₂	γ = 68.150 (1)°
M_r = 322.40	V = 860.80 (3) Å³
Triclinic, P1	Z = 2
a = 9.8039 (2) Å	Mo Kα radiation
b = 10.4453 (2) Å	µ = 0.08 mm⁻¹
c = 10.6765 (2) Å	T = 293 K
α = 62.208 (1)°	0.22 × 0.20 × 0.20 mm
β = 66.009 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3562 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2929 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.984	R_int = 0.028
12912 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.04	Δρ_max = 0.56 e Å⁻³
3531 reflections	Δρ_min = −0.21 e Å⁻³
217 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.8259 (2)	0.13083 (19)	−0.42562 (19)	0.0716 (5)
H1	0.8464	0.0451	−0.4428	0.086*
C2	0.9233 (2)	0.14731 (18)	−0.37349 (19)	0.0687 (4)
H2	1.0097	0.0725	−0.3554	0.082*
C3	0.89322 (16)	0.27493 (16)	−0.34793 (16)	0.0557 (3)
H3	0.9605	0.2865	−0.3147	0.067*
C4	0.76373 (14)	0.38484 (14)	−0.37167 (13)	0.0462 (3)
C5	0.6671 (2)	0.3663 (2)	−0.4234 (2)	0.0706 (4)
H5	0.5791	0.4396	−0.4391	0.085*
C6	0.6987 (2)	0.2410 (2)	−0.4522 (2)	0.0805 (5)
H6	0.6338	0.2313	−0.4895	0.097*
C7	0.75109 (14)	0.87255 (14)	0.19275 (14)	0.0459 (3)
C8	0.68184 (17)	0.89913 (16)	0.32258 (16)	0.0555 (3)
H8	0.6521	0.8227	0.4115	0.067*
C9	0.65695 (19)	1.03945 (18)	0.32005 (18)	0.0655 (4)
H9	0.6091	1.0571	0.4075	0.079*
C10	0.7016 (2)	1.15236 (17)	0.1911 (2)	0.0705 (4)
H10	0.6842	1.2465	0.1904	0.085*
C11	0.7722 (2)	1.12603 (19)	0.0627 (2)	0.0797 (5)
H11	0.8044	1.2023	−0.0254	0.096*
C12	0.7961 (2)	0.98681 (18)	0.06295 (17)	0.0687 (4)
H12	0.8428	0.9704	−0.0251	0.082*
C13	0.74162 (16)	0.54026 (13)	0.13846 (15)	0.0491 (3)
H13A	0.6493	0.5026	0.1824	0.059*
H13B	0.8142	0.4717	0.1942	0.059*
C14	0.80986 (15)	0.55186 (13)	−0.02091 (15)	0.0489 (3)
H14A	0.8293	0.4553	−0.0244	0.059*
H14B	0.9072	0.5801	−0.0608	0.059*
C15	0.70474 (15)	0.66528 (13)	−0.11683 (15)	0.0485 (3)
H15	0.6124	0.6289	−0.0839	0.058*
C16	0.65720 (17)	0.81395 (14)	−0.09792 (16)	0.0545 (3)
H16A	0.7453	0.8581	−0.1435	0.065*
H16B	0.5798	0.8810	−0.1483	0.065*
C17	0.59429 (16)	0.79586 (15)	0.06342 (16)	0.0535 (3)
H17A	0.5726	0.8908	0.0712	0.064*
H17B	0.4992	0.7629	0.1067	0.064*
C18	0.78445 (14)	0.71670 (14)	0.20002 (14)	0.0455 (3)
C19	0.78213 (19)	0.68686 (15)	−0.27908 (16)	0.0573 (3)
H19A	0.7154	0.7658	−0.3369	0.069*
H19B	0.8762	0.7184	−0.3109	0.069*
C20	0.71745 (15)	0.52476 (14)	−0.34233 (14)	0.0483 (3)
N1	0.70509 (12)	0.68746 (11)	0.14379 (12)	0.0470 (3)
N2	0.81811 (14)	0.55385 (12)	−0.30954 (13)	0.0534 (3)
H2A	0.9056	0.4929	−0.3064	0.064*
O1	0.59104 (12)	0.60806 (12)	−0.34789 (13)	0.0697 (3)
O2	0.88170 (13)	0.62016 (11)	0.25938 (13)	0.0689 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0865 (11)	0.0708 (10)	0.0764 (10)	−0.0293 (9)	−0.0096 (9)	−0.0448 (9)
C2	0.0719 (10)	0.0632 (9)	0.0812 (11)	−0.0047 (7)	−0.0229 (8)	−0.0417 (8)
C3	0.0563 (8)	0.0607 (8)	0.0644 (8)	−0.0080 (6)	−0.0217 (6)	−0.0346 (7)
C4	0.0523 (7)	0.0514 (7)	0.0393 (6)	−0.0144 (5)	−0.0127 (5)	−0.0186 (5)
C5	0.0704 (10)	0.0781 (11)	0.0874 (11)	−0.0067 (8)	−0.0393 (9)	−0.0430 (9)
C6	0.0848 (12)	0.0992 (13)	0.0971 (13)	−0.0290 (10)	−0.0304 (10)	−0.0573 (11)
C7	0.0473 (7)	0.0477 (7)	0.0529 (7)	−0.0087 (5)	−0.0160 (5)	−0.0267 (6)
C8	0.0653 (8)	0.0561 (8)	0.0526 (7)	−0.0163 (6)	−0.0129 (6)	−0.0274 (6)
C9	0.0734 (10)	0.0675 (9)	0.0698 (9)	−0.0176 (7)	−0.0082 (8)	−0.0455 (8)
C10	0.0833 (11)	0.0542 (8)	0.0871 (11)	−0.0199 (8)	−0.0168 (9)	−0.0393 (8)
C11	0.1130 (14)	0.0594 (9)	0.0692 (10)	−0.0401 (9)	−0.0106 (10)	−0.0232 (8)
C12	0.0919 (11)	0.0662 (9)	0.0542 (8)	−0.0308 (8)	−0.0042 (8)	−0.0314 (7)
C13	0.0590 (7)	0.0381 (6)	0.0579 (8)	−0.0068 (5)	−0.0231 (6)	−0.0217 (5)
C14	0.0568 (7)	0.0382 (6)	0.0582 (8)	−0.0033 (5)	−0.0214 (6)	−0.0244 (5)
C15	0.0561 (7)	0.0432 (7)	0.0580 (8)	−0.0076 (5)	−0.0229 (6)	−0.0251 (6)
C16	0.0682 (8)	0.0403 (7)	0.0666 (8)	0.0011 (6)	−0.0362 (7)	−0.0249 (6)
C17	0.0558 (7)	0.0474 (7)	0.0720 (9)	0.0045 (6)	−0.0318 (7)	−0.0344 (6)
C18	0.0471 (6)	0.0467 (7)	0.0497 (7)	−0.0062 (5)	−0.0158 (5)	−0.0249 (5)
C19	0.0773 (9)	0.0465 (7)	0.0576 (8)	−0.0108 (6)	−0.0268 (7)	−0.0228 (6)
C20	0.0530 (7)	0.0493 (7)	0.0442 (6)	−0.0080 (6)	−0.0163 (5)	−0.0190 (5)
N1	0.0534 (6)	0.0408 (5)	0.0580 (6)	−0.0019 (4)	−0.0242 (5)	−0.0265 (5)
N2	0.0609 (7)	0.0520 (6)	0.0609 (7)	−0.0032 (5)	−0.0262 (5)	−0.0314 (5)
O1	0.0602 (6)	0.0635 (6)	0.0921 (8)	0.0024 (5)	−0.0320 (6)	−0.0379 (6)
O2	0.0756 (7)	0.0571 (6)	0.0973 (8)	0.0054 (5)	−0.0534 (6)	−0.0382 (6)

Geometric parameters (Å, º) top

C1—C6	1.369 (3)	C13—N1	1.4665 (14)
C1—C2	1.377 (2)	C13—C14	1.5166 (18)
C1—H1	0.9300	C13—H13A	0.9700
C2—C3	1.3854 (19)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.5272 (18)
C3—C4	1.3782 (19)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.3788 (19)	C15—C19	1.5236 (19)
C4—C20	1.5026 (17)	C15—C16	1.5319 (16)
C5—C6	1.378 (2)	C15—H15	0.9800
C5—H5	0.9300	C16—C17	1.517 (2)
C6—H6	0.9300	C16—H16A	0.9700
C7—C12	1.376 (2)	C16—H16B	0.9700
C7—C8	1.3830 (18)	C17—N1	1.4610 (16)
C7—C18	1.5065 (16)	C17—H17A	0.9700
C8—C9	1.3823 (19)	C17—H17B	0.9700
C8—H8	0.9300	C18—O2	1.2277 (15)
C9—C10	1.363 (2)	C18—N1	1.3367 (16)
C9—H9	0.9300	C19—N2	1.4573 (16)
C10—C11	1.369 (2)	C19—H19A	0.9700
C10—H10	0.9300	C19—H19B	0.9700
C11—C12	1.383 (2)	C20—O1	1.2270 (16)
C11—H11	0.9300	C20—N2	1.3387 (17)
C12—H12	0.9300	N2—H2A	0.8600

C6—C1—C2	119.84 (14)	C13—C14—C15	112.38 (10)
C6—C1—H1	120.1	C13—C14—H14A	109.1
C2—C1—H1	120.1	C15—C14—H14A	109.1
C1—C2—C3	120.26 (15)	C13—C14—H14B	109.1
C1—C2—H2	119.9	C15—C14—H14B	109.1
C3—C2—H2	119.9	H14A—C14—H14B	107.9
C4—C3—C2	120.12 (13)	C19—C15—C14	111.50 (11)
C4—C3—H3	119.9	C19—C15—C16	109.95 (11)
C2—C3—H3	119.9	C14—C15—C16	109.78 (10)
C3—C4—C5	118.85 (13)	C19—C15—H15	108.5
C3—C4—C20	124.40 (11)	C14—C15—H15	108.5
C5—C4—C20	116.74 (12)	C16—C15—H15	108.5
C6—C5—C4	121.14 (15)	C17—C16—C15	111.99 (11)
C6—C5—H5	119.4	C17—C16—H16A	109.2
C4—C5—H5	119.4	C15—C16—H16A	109.2
C1—C6—C5	119.76 (14)	C17—C16—H16B	109.2
C1—C6—H6	120.1	C15—C16—H16B	109.2
C5—C6—H6	120.1	H16A—C16—H16B	107.9
C12—C7—C8	118.99 (12)	N1—C17—C16	110.21 (10)
C12—C7—C18	122.18 (12)	N1—C17—H17A	109.6
C8—C7—C18	118.70 (12)	C16—C17—H17A	109.6
C9—C8—C7	119.91 (13)	N1—C17—H17B	109.6
C9—C8—H8	120.0	C16—C17—H17B	109.6
C7—C8—H8	120.0	H17A—C17—H17B	108.1
C10—C9—C8	120.86 (14)	O2—C18—N1	122.09 (11)
C10—C9—H9	119.6	O2—C18—C7	119.08 (11)
C8—C9—H9	119.6	N1—C18—C7	118.82 (11)
C9—C10—C11	119.43 (14)	N2—C19—C15	113.75 (11)
C9—C10—H10	120.3	N2—C19—H19A	108.8
C11—C10—H10	120.3	C15—C19—H19A	108.8
C10—C11—C12	120.43 (15)	N2—C19—H19B	108.8
C10—C11—H11	119.8	C15—C19—H19B	108.8
C12—C11—H11	119.8	H19A—C19—H19B	107.7
C7—C12—C11	120.36 (14)	O1—C20—N2	121.84 (12)
C7—C12—H12	119.8	O1—C20—C4	120.44 (12)
C11—C12—H12	119.8	N2—C20—C4	117.72 (11)
N1—C13—C14	109.34 (10)	C18—N1—C17	126.14 (10)
N1—C13—H13A	109.8	C18—N1—C13	120.63 (10)
C14—C13—H13A	109.8	C17—N1—C13	112.60 (9)
N1—C13—H13B	109.8	C20—N2—C19	121.23 (11)
C14—C13—H13B	109.8	C20—N2—H2A	119.4
H13A—C13—H13B	108.3	C19—N2—H2A	119.4

C6—C1—C2—C3	−0.1 (3)	C12—C7—C18—O2	107.97 (17)
C1—C2—C3—C4	1.3 (2)	C8—C7—C18—O2	−67.72 (17)
C2—C3—C4—C5	−1.1 (2)	C12—C7—C18—N1	−73.19 (18)
C2—C3—C4—C20	177.72 (13)	C8—C7—C18—N1	111.12 (14)
C3—C4—C5—C6	−0.4 (2)	C14—C15—C19—N2	63.59 (15)
C20—C4—C5—C6	−179.32 (15)	C16—C15—C19—N2	−174.42 (11)
C2—C1—C6—C5	−1.4 (3)	C3—C4—C20—O1	−170.49 (13)
C4—C5—C6—C1	1.7 (3)	C5—C4—C20—O1	8.4 (2)
C12—C7—C8—C9	0.9 (2)	C3—C4—C20—N2	9.15 (19)
C18—C7—C8—C9	176.74 (12)	C5—C4—C20—N2	−172.00 (13)
C7—C8—C9—C10	−0.8 (2)	O2—C18—N1—C17	−176.01 (13)
C8—C9—C10—C11	−0.1 (3)	C7—C18—N1—C17	5.18 (19)
C9—C10—C11—C12	1.0 (3)	O2—C18—N1—C13	−5.8 (2)
C8—C7—C12—C11	0.0 (2)	C7—C18—N1—C13	175.39 (11)
C18—C7—C12—C11	−175.70 (15)	C16—C17—N1—C18	110.77 (14)
C10—C11—C12—C7	−1.0 (3)	C16—C17—N1—C13	−60.11 (14)
N1—C13—C14—C15	−56.11 (14)	C14—C13—N1—C18	−111.16 (13)
C13—C14—C15—C19	174.11 (10)	C14—C13—N1—C17	60.29 (14)
C13—C14—C15—C16	52.02 (15)	O1—C20—N2—C19	−0.2 (2)
C19—C15—C16—C17	−174.15 (11)	C4—C20—N2—C19	−179.78 (11)
C14—C15—C16—C17	−51.14 (15)	C15—C19—N2—C20	89.66 (15)
C15—C16—C17—N1	55.05 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.97	2.60	3.5548 (18)	169
C3—H3···O2ⁱⁱ	0.93	2.47	3.3803 (17)	167
N2—H2A···O2ⁱⁱ	0.86	2.11	2.9401 (15)	162
C8—H8···O1ⁱⁱⁱ	0.93	2.52	3.4506 (19)	176

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