N-[(1-Benzoyl-piperidin-4-yl)meth-yl]benzamide.

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 mol-ecules into inversion dimers. C-H⋯O inter-actions further link the mol-ecules, forming a three-dimensional supramolecular network.

Related literature

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

Crystal data

C20H22N2O2

M = 322.40

Triclinic,

a = 9.8039 (2) Å

b = 10.4453 (2) Å

c = 10.6765 (2) Å

α = 62.208 (1)°

β = 66.009 (1)°

γ = 68.150 (1)°

V = 860.80 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.22 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.982, T max = 0.984

12912 measured reflections

3562 independent reflections

2929 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.04

3531 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.21 e Å−3

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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814012793/bt6968sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012793/bt6968Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012793/bt6968Isup3.cml

CCDC reference: 987515

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H22N2O2	Z = 2
Mr = 322.40	F(000) = 344
Triclinic, P1	Dx = 1.244 Mg m−3Dm = 1.188 Mg m−3Dm 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

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

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(Fo2) + (0.0625P)2 + 0.1352P] where P = (Fo2 + 2Fc2)/3
3531 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) .