[(4E)-3-Ethyl-1-methyl-2,6-di-phenyl-piperidin-4-yl-idene]amino 3-methyl-benzoate.

In the title compound, C28H30N2O2, the piperidine ring exists in a chair conformation with an equatorial orientation of the phenyl rings and methyl group substituted on the heterocycle. In the crystal, C-H⋯π inter-actions result in chains of mol-ecules running parallel to the a-axis direction.

Related literature

For the synthesis and background to the biological activity of piperidinyl-4-one derivatives, see: Parthiban et al. (2009 ▶, 2011 ▶). For crystal structures of related compounds, see: Park et al. (2012a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H30N2O2

M = 426.54

Triclinic,

a = 10.5220 (15) Å

b = 11.8295 (16) Å

c = 11.987 (3) Å

α = 112.871 (11)°

β = 97.939 (11)°

γ = 110.123 (8)°

V = 1225.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.986, T max = 0.986

18615 measured reflections

5042 independent reflections

3610 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.139

S = 1.03

5042 reflections

292 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813024276/pv2635sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813024276/pv2635Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813024276/pv2635Isup3.cml

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

C28H30N2O2	Z = 2
Mr = 426.54	F(000) = 456
Triclinic, P1	Dx = 1.156 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5220 (15) Å	Cell parameters from 5087 reflections
b = 11.8295 (16) Å	θ = 1.9–26.5°
c = 11.987 (3) Å	µ = 0.07 mm−1
α = 112.871 (11)°	T = 293 K
β = 97.939 (11)°	Block, colorless
γ = 110.123 (8)°	0.20 × 0.20 × 0.20 mm
V = 1225.5 (4) Å3

Bruker SMART APEXII CCD diffractometer	5042 independent reflections
Radiation source: fine-focus sealed tube	3610 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.986, Tmax = 0.986	k = −14→14
18615 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.1881P] where P = (Fo2 + 2Fc2)/3
5042 reflections	(Δ/σ)max < 0.001
292 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.17 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	0.89609 (15)	0.09484 (14)	0.34733 (14)	0.0517 (3)
H1	0.9758	0.0793	0.3798	0.062*
C2	0.88999 (15)	0.21364 (15)	0.45884 (13)	0.0532 (3)
H2	0.8121	0.2300	0.4241	0.064*
C3	1.02600 (15)	0.33834 (14)	0.49960 (14)	0.0535 (3)
C4	1.04934 (17)	0.37330 (15)	0.39518 (14)	0.0571 (4)
H4A	1.1390	0.4536	0.4267	0.069*
H4B	0.9733	0.3934	0.3654	0.069*
C5	1.05203 (15)	0.25298 (14)	0.28511 (13)	0.0517 (3)
H5	1.1339	0.2390	0.3154	0.062*
C6	0.76059 (16)	−0.03556 (14)	0.29564 (14)	0.0542 (4)
C7	0.7643 (2)	−0.15236 (18)	0.29179 (19)	0.0775 (5)
H7	0.8509	−0.1509	0.3238	0.093*
C8	0.6392 (3)	−0.27266 (19)	0.2404 (2)	0.0977 (7)
H8	0.6432	−0.3515	0.2361	0.117*
C9	0.5122 (3)	−0.2753 (2)	0.1966 (2)	0.0937 (6)
H9	0.4288	−0.3555	0.1635	0.112*
C10	0.5065 (2)	−0.1611 (2)	0.20100 (19)	0.0807 (5)
H10	0.4189	−0.1630	0.1713	0.097*
C11	0.62958 (17)	−0.04179 (16)	0.24912 (16)	0.0639 (4)
H11	0.6241	0.0354	0.2502	0.077*
C12	0.85682 (19)	0.18214 (18)	0.56631 (16)	0.0724 (5)
H12A	0.7807	0.0907	0.5294	0.087*
H12B	0.9405	0.1839	0.6139	0.087*
C13	0.8129 (2)	0.2812 (3)	0.6574 (2)	0.1013 (7)
H13A	0.8910	0.3707	0.7004	0.152*
H13B	0.7872	0.2525	0.7191	0.152*
H13C	0.7327	0.2832	0.6105	0.152*
C14	1.31474 (16)	0.59266 (16)	0.75477 (14)	0.0573 (4)
C15	1.43652 (16)	0.71158 (16)	0.76655 (15)	0.0590 (4)
C16	1.51466 (19)	0.81891 (18)	0.88722 (18)	0.0763 (5)
H16	1.4912	0.8145	0.9579	0.092*
C17	1.6272 (2)	0.9324 (2)	0.9027 (3)	0.0959 (7)
H17	1.6793	1.0050	0.9839	0.115*
C18	1.6625 (2)	0.9387 (2)	0.7998 (3)	0.0988 (8)
H18	1.7391	1.0160	0.8119	0.119*
C19	1.5872 (2)	0.8331 (2)	0.6777 (2)	0.0920 (7)
C20	1.47272 (18)	0.71950 (19)	0.66290 (18)	0.0723 (5)
H20	1.4196	0.6475	0.5815	0.087*
C21	1.6253 (3)	0.8389 (4)	0.5631 (3)	0.1622 (15)
H21A	1.5714	0.8753	0.5285	0.243*
H21B	1.6037	0.7487	0.4997	0.243*
H21C	1.7253	0.8963	0.5878	0.243*
C22	1.07151 (17)	0.28834 (14)	0.17812 (14)	0.0547 (4)
C23	1.19935 (19)	0.31668 (16)	0.15166 (16)	0.0679 (4)
H23	1.2729	0.3102	0.1977	0.081*
C24	1.2191 (3)	0.35446 (18)	0.0577 (2)	0.0875 (6)
H24	1.3055	0.3727	0.0408	0.105*
C25	1.1128 (3)	0.36531 (19)	−0.0108 (2)	0.0965 (7)
H25	1.1268	0.3912	−0.0738	0.116*
C26	0.9851 (3)	0.3376 (2)	0.01431 (18)	0.0893 (6)
H26	0.9123	0.3446	−0.0321	0.107*
C27	0.9640 (2)	0.29925 (17)	0.10809 (15)	0.0687 (4)
H27	0.8771	0.2807	0.1243	0.082*
C28	0.9312 (2)	0.01436 (16)	0.14152 (17)	0.0701 (5)
H28A	0.9489	0.0364	0.0744	0.105*
H28B	0.8433	−0.0664	0.1083	0.105*
H28C	1.0079	−0.0012	0.1756	0.105*
N1	0.92147 (12)	0.12787 (11)	0.24286 (11)	0.0493 (3)
N2	1.10892 (13)	0.39464 (13)	0.61306 (12)	0.0616 (3)
O1	1.23463 (11)	0.50961 (11)	0.63113 (10)	0.0681 (3)
O2	1.28828 (14)	0.57319 (14)	0.84073 (11)	0.0882 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0478 (8)	0.0499 (8)	0.0622 (8)	0.0209 (7)	0.0187 (7)	0.0307 (7)
C2	0.0504 (8)	0.0505 (8)	0.0542 (8)	0.0156 (7)	0.0179 (6)	0.0255 (7)
C3	0.0539 (8)	0.0482 (8)	0.0518 (8)	0.0164 (7)	0.0176 (7)	0.0222 (7)
C4	0.0621 (9)	0.0454 (8)	0.0526 (8)	0.0131 (7)	0.0163 (7)	0.0221 (7)
C5	0.0467 (8)	0.0494 (8)	0.0586 (8)	0.0176 (7)	0.0188 (6)	0.0270 (7)
C6	0.0576 (9)	0.0454 (8)	0.0618 (8)	0.0195 (7)	0.0245 (7)	0.0279 (7)
C7	0.0865 (13)	0.0599 (11)	0.1044 (14)	0.0362 (10)	0.0408 (11)	0.0483 (10)
C8	0.126 (2)	0.0494 (11)	0.1286 (18)	0.0337 (12)	0.0604 (16)	0.0492 (12)
C9	0.0915 (16)	0.0567 (12)	0.1021 (15)	0.0041 (11)	0.0354 (12)	0.0313 (11)
C10	0.0603 (11)	0.0702 (12)	0.0894 (13)	0.0080 (9)	0.0193 (9)	0.0360 (10)
C11	0.0579 (9)	0.0524 (9)	0.0750 (10)	0.0160 (8)	0.0192 (8)	0.0312 (8)
C12	0.0696 (11)	0.0687 (11)	0.0636 (10)	0.0087 (9)	0.0225 (8)	0.0348 (9)
C13	0.0995 (16)	0.1203 (18)	0.0744 (12)	0.0333 (14)	0.0482 (11)	0.0423 (12)
C14	0.0551 (9)	0.0585 (9)	0.0520 (8)	0.0213 (8)	0.0133 (7)	0.0241 (7)
C15	0.0485 (8)	0.0579 (9)	0.0647 (9)	0.0204 (7)	0.0097 (7)	0.0285 (8)
C16	0.0624 (11)	0.0660 (11)	0.0757 (11)	0.0228 (9)	0.0083 (9)	0.0190 (9)
C17	0.0648 (12)	0.0629 (12)	0.1178 (18)	0.0174 (10)	0.0008 (12)	0.0214 (12)
C18	0.0517 (11)	0.0727 (14)	0.159 (2)	0.0133 (10)	0.0089 (13)	0.0625 (16)
C19	0.0600 (11)	0.1018 (16)	0.1250 (18)	0.0199 (12)	0.0197 (12)	0.0798 (15)
C20	0.0551 (9)	0.0785 (12)	0.0759 (11)	0.0147 (9)	0.0111 (8)	0.0449 (10)
C21	0.1018 (19)	0.216 (4)	0.180 (3)	0.011 (2)	0.0387 (19)	0.156 (3)
C22	0.0625 (9)	0.0416 (7)	0.0548 (8)	0.0174 (7)	0.0242 (7)	0.0205 (6)
C23	0.0717 (11)	0.0522 (9)	0.0771 (11)	0.0199 (8)	0.0379 (9)	0.0292 (8)
C24	0.1104 (16)	0.0569 (11)	0.0910 (14)	0.0218 (11)	0.0622 (13)	0.0335 (10)
C25	0.157 (2)	0.0591 (11)	0.0719 (12)	0.0315 (13)	0.0545 (14)	0.0364 (10)
C26	0.1257 (18)	0.0718 (12)	0.0653 (11)	0.0371 (12)	0.0196 (11)	0.0359 (10)
C27	0.0769 (11)	0.0651 (10)	0.0615 (9)	0.0275 (9)	0.0206 (8)	0.0307 (8)
C28	0.0791 (11)	0.0522 (9)	0.0778 (11)	0.0282 (9)	0.0415 (9)	0.0241 (8)
N1	0.0489 (7)	0.0413 (6)	0.0549 (6)	0.0166 (5)	0.0219 (5)	0.0207 (5)
N2	0.0531 (7)	0.0586 (8)	0.0584 (8)	0.0078 (6)	0.0162 (6)	0.0285 (6)
O1	0.0575 (7)	0.0676 (7)	0.0544 (6)	0.0030 (6)	0.0117 (5)	0.0287 (5)
O2	0.0914 (9)	0.0885 (9)	0.0587 (7)	0.0120 (7)	0.0212 (6)	0.0347 (7)

C1—N1	1.4809 (17)	C14—O1	1.3511 (18)
C1—C6	1.515 (2)	C14—C15	1.482 (2)
C1—C2	1.547 (2)	C15—C20	1.376 (2)
C1—H1	0.9800	C15—C16	1.381 (2)
C2—C3	1.502 (2)	C16—C17	1.375 (3)
C2—C12	1.526 (2)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.358 (3)
C3—N2	1.2740 (19)	C17—H17	0.9300
C3—C4	1.4884 (19)	C18—C19	1.381 (3)
C4—C5	1.532 (2)	C18—H18	0.9300
C4—H4A	0.9700	C19—C20	1.390 (2)
C4—H4B	0.9700	C19—C21	1.503 (3)
C5—N1	1.4699 (17)	C20—H20	0.9300
C5—C22	1.5142 (19)	C21—H21A	0.9600
C5—H5	0.9800	C21—H21B	0.9600
C6—C11	1.379 (2)	C21—H21C	0.9600
C6—C7	1.379 (2)	C22—C23	1.383 (2)
C7—C8	1.394 (3)	C22—C27	1.387 (2)
C7—H7	0.9300	C23—C24	1.380 (3)
C8—C9	1.352 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.367 (3)
C9—C10	1.354 (3)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.375 (3)
C10—C11	1.380 (2)	C25—H25	0.9300
C10—H10	0.9300	C26—C27	1.384 (2)
C11—H11	0.9300	C26—H26	0.9300
C12—C13	1.516 (3)	C27—H27	0.9300
C12—H12A	0.9700	C28—N1	1.4666 (19)
C12—H12B	0.9700	C28—H28A	0.9600
C13—H13A	0.9600	C28—H28B	0.9600
C13—H13B	0.9600	C28—H28C	0.9600
C13—H13C	0.9600	N2—O1	1.4492 (16)
C14—O2	1.1883 (18)
N1—C1—C6	109.65 (11)	O2—C14—O1	124.24 (15)
N1—C1—C2	111.57 (11)	O2—C14—C15	125.66 (14)
C6—C1—C2	111.31 (11)	O1—C14—C15	110.08 (13)
N1—C1—H1	108.1	C20—C15—C16	119.39 (16)
C6—C1—H1	108.1	C20—C15—C14	122.82 (15)
C2—C1—H1	108.1	C16—C15—C14	117.79 (16)
C3—C2—C12	114.71 (12)	C17—C16—C15	119.9 (2)
C3—C2—C1	107.06 (11)	C17—C16—H16	120.1
C12—C2—C1	113.67 (12)	C15—C16—H16	120.1
C3—C2—H2	107.0	C18—C17—C16	120.2 (2)
C12—C2—H2	107.0	C18—C17—H17	119.9
C1—C2—H2	107.0	C16—C17—H17	119.9
N2—C3—C4	128.60 (13)	C17—C18—C19	121.6 (2)
N2—C3—C2	117.74 (13)	C17—C18—H18	119.2
C4—C3—C2	113.50 (12)	C19—C18—H18	119.2
C3—C4—C5	109.35 (12)	C18—C19—C20	117.8 (2)
C3—C4—H4A	109.8	C18—C19—C21	122.1 (2)
C5—C4—H4A	109.8	C20—C19—C21	120.2 (2)
C3—C4—H4B	109.8	C15—C20—C19	121.16 (18)
C5—C4—H4B	109.8	C15—C20—H20	119.4
H4A—C4—H4B	108.3	C19—C20—H20	119.4
N1—C5—C22	111.99 (11)	C19—C21—H21A	109.5
N1—C5—C4	110.54 (11)	C19—C21—H21B	109.5
C22—C5—C4	108.78 (11)	H21A—C21—H21B	109.5
N1—C5—H5	108.5	C19—C21—H21C	109.5
C22—C5—H5	108.5	H21A—C21—H21C	109.5
C4—C5—H5	108.5	H21B—C21—H21C	109.5
C11—C6—C7	117.80 (15)	C23—C22—C27	118.32 (15)
C11—C6—C1	121.02 (12)	C23—C22—C5	120.77 (15)
C7—C6—C1	121.17 (14)	C27—C22—C5	120.84 (14)
C6—C7—C8	120.51 (19)	C24—C23—C22	120.75 (19)
C6—C7—H7	119.7	C24—C23—H23	119.6
C8—C7—H7	119.7	C22—C23—H23	119.6
C9—C8—C7	120.33 (18)	C25—C24—C23	120.65 (19)
C9—C8—H8	119.8	C25—C24—H24	119.7
C7—C8—H8	119.8	C23—C24—H24	119.7
C8—C9—C10	119.89 (19)	C24—C25—C26	119.32 (18)
C8—C9—H9	120.1	C24—C25—H25	120.3
C10—C9—H9	120.1	C26—C25—H25	120.3
C9—C10—C11	120.6 (2)	C25—C26—C27	120.5 (2)
C9—C10—H10	119.7	C25—C26—H26	119.7
C11—C10—H10	119.7	C27—C26—H26	119.7
C6—C11—C10	120.88 (16)	C26—C27—C22	120.43 (18)
C6—C11—H11	119.6	C26—C27—H27	119.8
C10—C11—H11	119.6	C22—C27—H27	119.8
C13—C12—C2	113.43 (16)	N1—C28—H28A	109.5
C13—C12—H12A	108.9	N1—C28—H28B	109.5
C2—C12—H12A	108.9	H28A—C28—H28B	109.5
C13—C12—H12B	108.9	N1—C28—H28C	109.5
C2—C12—H12B	108.9	H28A—C28—H28C	109.5
H12A—C12—H12B	107.7	H28B—C28—H28C	109.5
C12—C13—H13A	109.5	C28—N1—C5	108.74 (11)
C12—C13—H13B	109.5	C28—N1—C1	109.56 (11)
H13A—C13—H13B	109.5	C5—N1—C1	113.06 (11)
C12—C13—H13C	109.5	C3—N2—O1	108.75 (11)
H13A—C13—H13C	109.5	C14—O1—N2	113.11 (11)
H13B—C13—H13C	109.5
N1—C1—C2—C3	−55.08 (15)	C16—C17—C18—C19	0.3 (3)
C6—C1—C2—C3	−177.93 (11)	C17—C18—C19—C20	0.4 (3)
N1—C1—C2—C12	177.19 (12)	C17—C18—C19—C21	−179.9 (2)
C6—C1—C2—C12	54.34 (16)	C16—C15—C20—C19	0.5 (3)
C12—C2—C3—N2	9.1 (2)	C14—C15—C20—C19	179.61 (16)
C1—C2—C3—N2	−118.05 (15)	C18—C19—C20—C15	−0.8 (3)
C12—C2—C3—C4	−175.05 (13)	C21—C19—C20—C15	179.5 (2)
C1—C2—C3—C4	57.83 (16)	N1—C5—C22—C23	−129.64 (14)
N2—C3—C4—C5	116.68 (18)	C4—C5—C22—C23	107.88 (16)
C2—C3—C4—C5	−58.66 (17)	N1—C5—C22—C27	53.35 (18)
C3—C4—C5—N1	55.01 (16)	C4—C5—C22—C27	−69.13 (17)
C3—C4—C5—C22	178.37 (12)	C27—C22—C23—C24	−0.2 (2)
N1—C1—C6—C11	−65.70 (17)	C5—C22—C23—C24	−177.26 (14)
C2—C1—C6—C11	58.24 (18)	C22—C23—C24—C25	0.3 (3)
N1—C1—C6—C7	113.34 (16)	C23—C24—C25—C26	−0.3 (3)
C2—C1—C6—C7	−122.72 (16)	C24—C25—C26—C27	0.1 (3)
C11—C6—C7—C8	1.1 (3)	C25—C26—C27—C22	0.0 (3)
C1—C6—C7—C8	−178.01 (16)	C23—C22—C27—C26	0.0 (2)
C6—C7—C8—C9	−1.7 (3)	C5—C22—C27—C26	177.10 (15)
C7—C8—C9—C10	0.9 (3)	C22—C5—N1—C28	61.00 (15)
C8—C9—C10—C11	0.4 (3)	C4—C5—N1—C28	−177.53 (12)
C7—C6—C11—C10	0.3 (2)	C22—C5—N1—C1	−177.08 (11)
C1—C6—C11—C10	179.37 (15)	C4—C5—N1—C1	−55.61 (14)
C9—C10—C11—C6	−1.1 (3)	C6—C1—N1—C28	−58.12 (15)
C3—C2—C12—C13	71.5 (2)	C2—C1—N1—C28	178.09 (12)
C1—C2—C12—C13	−164.88 (15)	C6—C1—N1—C5	−179.58 (11)
O2—C14—C15—C20	170.94 (17)	C2—C1—N1—C5	56.63 (15)
O1—C14—C15—C20	−10.5 (2)	C4—C3—N2—O1	3.1 (2)
O2—C14—C15—C16	−10.0 (2)	C2—C3—N2—O1	178.31 (12)
O1—C14—C15—C16	168.57 (14)	O2—C14—O1—N2	1.7 (2)
C20—C15—C16—C17	0.2 (3)	C15—C14—O1—N2	−176.83 (11)
C14—C15—C16—C17	−178.97 (16)	C3—N2—O1—C14	166.95 (14)
C15—C16—C17—C18	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···Cg1i	0.93	2.93	3.761 (2)	149
C23—H23···Cg1ii	0.93	2.89	3.730 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯Cg1i	0.93	2.93	3.761 (2)	149
C23—H23⋯Cg1ii	0.93	2.89	3.730 (3)	151

Symmetry codes: (i) ; (ii) .