Crystal structure of 4-methyl-N-{[1-(4-methyl-benzo-yl)piperidin-4-yl]meth-yl}benzamide.

In the title compound, C22H27N2O2, the piperidine ring adopts a half-chair conformation with the benzene rings inclined in a trans orientation with respect to the piperidine ring [dihedral angle between the benzene rings = 89.1 (1)°]. In the crystal, a three-centre asymmetric N-H⋯O/C-H⋯O hydrogen-bonding inter-action leads to the formation of chains extending along the a-axis direction.

Related literature

For the synthesis of the title compound, see: Prathebha et al. (2013 ▶, 2014 ▶). For the biological activity of piperdine derivatives, see: Prostakov & Gaivoronskaya (1978 ▶); O’Hagan (2000 ▶); Pinder (1992 ▶). For related structures, see: Prathebha et al. (2014 ▶); Luo et al. (2011 ▶).

Experimental

Crystal data

C22H26N2O2

M = 350.45

Orthorhombic,

a = 15.3749 (6) Å

b = 13.1575 (5) Å

c = 19.2929 (9) Å

V = 3902.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.975, T max = 0.998

26551 measured reflections

4831 independent reflections

1847 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.172

S = 0.93

4831 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 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: SHELXS97 (Sheldrick, 2008 ▶); 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/S1600536814021965/zs2314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814021965/zs2314Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814021965/zs2314Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814021965/zs2314fig1.tif

The mol­ecular structure of the title compound showing atom numbering, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814021965/zs2314fig2.tif

The packing of the mol­ecules in the crystal structure. Unassociated H-atoms are omitted and dashed lines indicate the hydrogen bonds.

Click here for additional data file.

. DOI: 10.1107/S1600536814021965/zs2314fig3.tif

Experimental procedure

CCDC reference: 1027556

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

C22H26N2O2	F(000) = 1504
Mr = 350.45	Dx = 1.193 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4831 reflections
a = 15.3749 (6) Å	θ = 2.3–28.3°
b = 13.1575 (5) Å	µ = 0.08 mm−1
c = 19.2929 (9) Å	T = 293 K
V = 3902.9 (3) Å3	Block, colourless
Z = 8	0.20 × 0.15 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	4831 independent reflections
Radiation source: fine-focus sealed tube	1847 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω and φ scan	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −17→20
Tmin = 0.975, Tmax = 0.998	k = −17→12
26551 measured reflections	l = −12→25

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0588P)2 + 1.589P] where P = (Fo2 + 2Fc2)/3
4831 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 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
C22	0.6965 (2)	−0.4676 (2)	0.47887 (18)	0.0948 (10)
H22A	0.7516	−0.4377	0.4902	0.114*
H22B	0.7033	−0.5122	0.4399	0.114*
H22C	0.6753	−0.5055	0.5179	0.114*
N1	0.24058 (14)	0.06231 (14)	0.21465 (13)	0.0678 (7)
C1	−0.00836 (15)	0.31788 (17)	0.17840 (14)	0.0539 (7)
C2	0.03275 (17)	0.28524 (18)	0.11916 (15)	0.0634 (7)
H2	0.0216	0.3183	0.0775	0.076*
C3	0.08988 (16)	0.20487 (19)	0.12001 (15)	0.0631 (7)
H3	0.1158	0.1835	0.0790	0.076*
C4	0.10897 (14)	0.15576 (17)	0.18134 (14)	0.0504 (6)
C5	0.06856 (16)	0.18834 (19)	0.24129 (14)	0.0566 (7)
H5	0.0809	0.1563	0.2831	0.068*
C6	0.01028 (15)	0.26771 (18)	0.23982 (14)	0.0571 (7)
H6	−0.0170	0.2880	0.2806	0.069*
C7	−0.07222 (18)	0.4045 (2)	0.17671 (17)	0.0831 (9)
H7A	−0.0943	0.4163	0.2225	0.100*
H7B	−0.1195	0.3878	0.1462	0.100*
H7C	−0.0436	0.4647	0.1603	0.100*
C8	0.16482 (16)	0.0623 (2)	0.18032 (15)	0.0582 (7)
C9	0.29448 (18)	−0.0291 (2)	0.21712 (17)	0.0756 (9)
H9A	0.3451	−0.0199	0.1878	0.091*
H9B	0.2616	−0.0865	0.1995	0.091*
C10	0.32335 (16)	−0.05074 (18)	0.29030 (15)	0.0653 (8)
H10A	0.3618	−0.1092	0.2904	0.078*
H10B	0.2730	−0.0672	0.3184	0.078*
C11	0.37020 (15)	0.03968 (18)	0.32161 (15)	0.0595 (7)
H11	0.4215	0.0535	0.2930	0.071*
C12	0.31090 (17)	0.13214 (18)	0.31724 (16)	0.0704 (8)
H12A	0.2602	0.1211	0.3463	0.084*
H12B	0.3415	0.1912	0.3348	0.084*
C13	0.28185 (17)	0.15248 (19)	0.24409 (17)	0.0758 (9)
H13A	0.2410	0.2087	0.2437	0.091*
H13B	0.3316	0.1714	0.2160	0.091*
C14	0.40150 (18)	0.0214 (2)	0.39565 (15)	0.0701 (8)
H14A	0.4287	0.0831	0.4126	0.084*
H14B	0.3514	0.0076	0.4247	0.084*
C15	0.43907 (18)	−0.1546 (2)	0.42462 (14)	0.0650 (7)
C16	0.50989 (17)	−0.2317 (2)	0.43383 (13)	0.0596 (7)
C17	0.48785 (18)	−0.3334 (2)	0.42988 (14)	0.0682 (8)
H17	0.4311	−0.3516	0.4186	0.082*
C18	0.5486 (2)	−0.4082 (2)	0.44237 (15)	0.0724 (8)
H18	0.5324	−0.4760	0.4381	0.087*
C19	0.63257 (19)	−0.3850 (2)	0.46102 (14)	0.0695 (8)
C20	0.65476 (19)	−0.2835 (2)	0.46459 (16)	0.0776 (9)
H20	0.7112	−0.2656	0.4770	0.093*
C21	0.59503 (18)	−0.2076 (2)	0.45019 (14)	0.0688 (8)
H21	0.6123	−0.1399	0.4515	0.083*
N2	0.46281 (13)	−0.06195 (16)	0.40288 (12)	0.0649 (6)
H2A	0.5165	−0.0514	0.3928	0.078*
O1	0.13858 (11)	−0.01377 (14)	0.14932 (11)	0.0784 (6)
O2	0.36348 (13)	−0.17709 (15)	0.43739 (12)	0.0903 (7)

	U11	U22	U33	U12	U13	U23
C22	0.094 (2)	0.103 (2)	0.088 (3)	0.014 (2)	−0.0037 (19)	0.0161 (19)
N1	0.0524 (13)	0.0512 (13)	0.0998 (19)	0.0038 (11)	−0.0208 (13)	−0.0054 (12)
C1	0.0500 (15)	0.0491 (14)	0.0626 (19)	0.0003 (12)	−0.0012 (13)	−0.0051 (13)
C2	0.0760 (19)	0.0608 (16)	0.0534 (18)	0.0120 (15)	−0.0029 (14)	0.0044 (13)
C3	0.0696 (18)	0.0681 (17)	0.0518 (18)	0.0097 (15)	0.0032 (13)	−0.0024 (14)
C4	0.0442 (14)	0.0494 (14)	0.0575 (17)	−0.0011 (11)	−0.0046 (12)	−0.0013 (13)
C5	0.0592 (17)	0.0620 (16)	0.0486 (17)	−0.0039 (14)	−0.0040 (13)	0.0010 (13)
C6	0.0566 (16)	0.0605 (16)	0.0543 (18)	−0.0043 (14)	0.0087 (13)	−0.0079 (13)
C7	0.079 (2)	0.0688 (18)	0.102 (3)	0.0132 (16)	0.0057 (17)	−0.0044 (17)
C8	0.0517 (16)	0.0571 (17)	0.0659 (19)	−0.0026 (13)	−0.0026 (14)	−0.0014 (14)
C9	0.0630 (18)	0.0685 (18)	0.095 (3)	0.0176 (15)	−0.0140 (16)	−0.0107 (17)
C10	0.0535 (16)	0.0542 (16)	0.088 (2)	0.0099 (13)	−0.0041 (15)	−0.0025 (15)
C11	0.0425 (14)	0.0619 (16)	0.074 (2)	−0.0021 (13)	0.0008 (13)	0.0039 (14)
C12	0.0559 (16)	0.0542 (16)	0.101 (3)	−0.0060 (13)	−0.0106 (16)	−0.0082 (15)
C13	0.0550 (17)	0.0574 (17)	0.115 (3)	−0.0053 (14)	−0.0228 (16)	0.0050 (17)
C14	0.0614 (17)	0.0717 (18)	0.077 (2)	−0.0026 (15)	0.0065 (15)	−0.0039 (15)
C15	0.0598 (19)	0.080 (2)	0.0554 (18)	−0.0082 (16)	0.0033 (14)	0.0081 (15)
C16	0.0611 (18)	0.0724 (19)	0.0451 (16)	−0.0070 (15)	−0.0011 (12)	0.0101 (13)
C17	0.0668 (18)	0.082 (2)	0.0558 (19)	−0.0141 (17)	−0.0077 (14)	0.0083 (15)
C18	0.084 (2)	0.0709 (19)	0.062 (2)	−0.0063 (18)	−0.0051 (15)	0.0078 (15)
C19	0.070 (2)	0.083 (2)	0.0557 (19)	0.0009 (17)	0.0004 (14)	0.0113 (15)
C20	0.0625 (19)	0.091 (2)	0.079 (2)	−0.0083 (18)	−0.0071 (15)	0.0125 (18)
C21	0.0663 (19)	0.0714 (18)	0.069 (2)	−0.0080 (16)	−0.0049 (15)	0.0095 (15)
N2	0.0518 (13)	0.0738 (15)	0.0691 (17)	−0.0011 (12)	0.0025 (11)	0.0105 (12)
O1	0.0663 (12)	0.0677 (12)	0.1013 (17)	0.0074 (10)	−0.0196 (11)	−0.0242 (11)
O2	0.0584 (13)	0.1027 (15)	0.1098 (18)	−0.0099 (11)	0.0146 (11)	0.0269 (13)

C22—C19	1.505 (4)	C10—H10A	0.9700
C22—H22A	0.9600	C10—H10B	0.9700
C22—H22B	0.9600	C11—C12	1.523 (3)
C22—H22C	0.9600	C11—C14	1.526 (4)
N1—C8	1.340 (3)	C11—H11	0.9800
N1—C13	1.460 (3)	C12—C13	1.504 (4)
N1—C9	1.461 (3)	C12—H12A	0.9700
C1—C2	1.375 (3)	C12—H12B	0.9700
C1—C6	1.386 (3)	C13—H13A	0.9700
C1—C7	1.505 (3)	C13—H13B	0.9700
C2—C3	1.375 (3)	C14—N2	1.452 (3)
C2—H2	0.9300	C14—H14A	0.9700
C3—C4	1.380 (3)	C14—H14B	0.9700
C3—H3	0.9300	C15—O2	1.224 (3)
C4—C5	1.381 (3)	C15—N2	1.340 (3)
C4—C8	1.500 (3)	C15—C16	1.499 (4)
C5—C6	1.376 (3)	C16—C17	1.382 (3)
C5—H5	0.9300	C16—C21	1.383 (3)
C6—H6	0.9300	C17—C18	1.379 (4)
C7—H7A	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—C19	1.374 (4)
C7—H7C	0.9600	C18—H18	0.9300
C8—O1	1.233 (3)	C19—C20	1.381 (4)
C9—C10	1.507 (4)	C20—C21	1.384 (4)
C9—H9A	0.9700	C20—H20	0.9300
C9—H9B	0.9700	C21—H21	0.9300
C10—C11	1.516 (3)	N2—H2A	0.8600
C19—C22—H22A	109.5	C10—C11—C12	108.7 (2)
C19—C22—H22B	109.5	C10—C11—C14	113.5 (2)
H22A—C22—H22B	109.5	C12—C11—C14	111.5 (2)
C19—C22—H22C	109.5	C10—C11—H11	107.6
H22A—C22—H22C	109.5	C12—C11—H11	107.6
H22B—C22—H22C	109.5	C14—C11—H11	107.6
C8—N1—C13	124.8 (2)	C13—C12—C11	111.8 (2)
C8—N1—C9	120.6 (2)	C13—C12—H12A	109.2
C13—N1—C9	114.2 (2)	C11—C12—H12A	109.2
C2—C1—C6	117.8 (2)	C13—C12—H12B	109.2
C2—C1—C7	121.2 (2)	C11—C12—H12B	109.2
C6—C1—C7	120.9 (2)	H12A—C12—H12B	107.9
C1—C2—C3	121.6 (2)	N1—C13—C12	110.4 (2)
C1—C2—H2	119.2	N1—C13—H13A	109.6
C3—C2—H2	119.2	C12—C13—H13A	109.6
C2—C3—C4	120.4 (2)	N1—C13—H13B	109.6
C2—C3—H3	119.8	C12—C13—H13B	109.6
C4—C3—H3	119.8	H13A—C13—H13B	108.1
C3—C4—C5	118.5 (2)	N2—C14—C11	114.4 (2)
C3—C4—C8	119.6 (2)	N2—C14—H14A	108.7
C5—C4—C8	121.5 (2)	C11—C14—H14A	108.7
C6—C5—C4	120.7 (2)	N2—C14—H14B	108.7
C6—C5—H5	119.6	C11—C14—H14B	108.7
C4—C5—H5	119.6	H14A—C14—H14B	107.6
C5—C6—C1	120.9 (2)	O2—C15—N2	122.8 (3)
C5—C6—H6	119.6	O2—C15—C16	120.2 (3)
C1—C6—H6	119.6	N2—C15—C16	117.1 (2)
C1—C7—H7A	109.5	C17—C16—C21	117.8 (3)
C1—C7—H7B	109.5	C17—C16—C15	118.1 (2)
H7A—C7—H7B	109.5	C21—C16—C15	124.0 (3)
C1—C7—H7C	109.5	C16—C17—C18	121.0 (3)
H7A—C7—H7C	109.5	C16—C17—H17	119.5
H7B—C7—H7C	109.5	C18—C17—H17	119.5
O1—C8—N1	121.6 (2)	C19—C18—C17	121.6 (3)
O1—C8—C4	119.0 (2)	C19—C18—H18	119.2
N1—C8—C4	119.4 (2)	C17—C18—H18	119.2
N1—C9—C10	110.7 (2)	C18—C19—C20	117.4 (3)
N1—C9—H9A	109.5	C18—C19—C22	120.9 (3)
C10—C9—H9A	109.5	C20—C19—C22	121.7 (3)
N1—C9—H9B	109.5	C19—C20—C21	121.6 (3)
C10—C9—H9B	109.5	C19—C20—H20	119.2
H9A—C9—H9B	108.1	C21—C20—H20	119.2
C9—C10—C11	111.4 (2)	C16—C21—C20	120.5 (3)
C9—C10—H10A	109.4	C16—C21—H21	119.7
C11—C10—H10A	109.4	C20—C21—H21	119.7
C9—C10—H10B	109.4	C15—N2—C14	122.7 (2)
C11—C10—H10B	109.4	C15—N2—H2A	118.7
H10A—C10—H10B	108.0	C14—N2—H2A	118.7
C6—C1—C2—C3	0.7 (4)	C14—C11—C12—C13	178.4 (2)
C7—C1—C2—C3	−178.7 (2)	C8—N1—C13—C12	132.7 (3)
C1—C2—C3—C4	−1.4 (4)	C9—N1—C13—C12	−55.1 (3)
C2—C3—C4—C5	0.8 (4)	C11—C12—C13—N1	55.1 (3)
C2—C3—C4—C8	174.3 (2)	C10—C11—C14—N2	60.6 (3)
C3—C4—C5—C6	0.3 (3)	C12—C11—C14—N2	−176.3 (2)
C8—C4—C5—C6	−173.0 (2)	O2—C15—C16—C17	25.0 (4)
C4—C5—C6—C1	−1.0 (3)	N2—C15—C16—C17	−155.7 (2)
C2—C1—C6—C5	0.5 (3)	O2—C15—C16—C21	−151.0 (3)
C7—C1—C6—C5	179.9 (2)	N2—C15—C16—C21	28.4 (4)
C13—N1—C8—O1	170.9 (3)	C21—C16—C17—C18	0.5 (4)
C9—N1—C8—O1	−0.8 (4)	C15—C16—C17—C18	−175.7 (2)
C13—N1—C8—C4	−11.1 (4)	C16—C17—C18—C19	1.8 (4)
C9—N1—C8—C4	177.3 (2)	C17—C18—C19—C20	−2.1 (4)
C3—C4—C8—O1	−63.0 (3)	C17—C18—C19—C22	176.1 (3)
C5—C4—C8—O1	110.2 (3)	C18—C19—C20—C21	0.2 (4)
C3—C4—C8—N1	118.9 (3)	C22—C19—C20—C21	−178.0 (3)
C5—C4—C8—N1	−67.9 (3)	C17—C16—C21—C20	−2.4 (4)
C8—N1—C9—C10	−132.0 (3)	C15—C16—C21—C20	173.6 (3)
C13—N1—C9—C10	55.5 (3)	C19—C20—C21—C16	2.1 (4)
N1—C9—C10—C11	−55.6 (3)	O2—C15—N2—C14	2.9 (4)
C9—C10—C11—C12	55.8 (3)	C16—C15—N2—C14	−176.4 (2)
C9—C10—C11—C14	−179.5 (2)	C11—C14—N2—C15	−99.6 (3)
C10—C11—C12—C13	−55.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.10	2.953 (3)	169
C21—H21···O1i	0.93	2.59	3.262 (3)	130
C9—H9B···O1	0.97	2.33	2.738 (3)	104
C14—H14B···O2	0.97	2.45	2.794 (3)	100

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2H2AO1i	0.86	2.10	2.953(3)	169
C21H21O1i	0.93	2.59	3.262(3)	130

Symmetry code: (i) .