Ethyl 4-anilino-2,6-bis-(4-chloro-phen-yl)-1-phenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

The title compound, C32H28Cl2N2O2, was synthesized by a multicomponent reaction of 4-chloro-benzaldehyde, aniline and ethyl aceto-acetate. The central 1,2,5,6-tetra-hydro-pyridine ring exhibits a distorted boat conformation and the two chloro-phenyl rings attached to the central ring at positions 2 and 6 are oriented in opposite directions. The two O atoms of the eth-oxy-carbonyl group are involved in intra-molecular N-H⋯O and C-H⋯O hydrogen bonds. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules related by translation along the b axis into chains.

Related literature

For applications of functionalized piperidines, see: Viegas et al. (2004 ▶); Kobayashi et al. (1999 ▶). For the crystal structures of related compounds, see: Khan et al. (2008 ▶); Brahmachari & Das (2012 ▶).

Experimental

Crystal data

C32H28Cl2N2O2

M = 543.46

Triclinic,

a = 9.559 (4) Å

b = 9.656 (3) Å

c = 16.392 (6) Å

α = 78.584 (6)°

β = 82.056 (6)°

γ = 68.390 (6)°

V = 1375.3 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.26 × 0.22 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.934, T max = 0.951

6863 measured reflections

4767 independent reflections

3177 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.310

S = 1.08

4767 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.47 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813013573/cv5409sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013573/cv5409Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013573/cv5409Isup3.cml

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

C32H28Cl2N2O2	Z = 2
Mr = 543.46	F(000) = 568
Triclinic, P1	Dx = 1.312 Mg m−3
a = 9.559 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.656 (3) Å	Cell parameters from 1798 reflections
c = 16.392 (6) Å	θ = 2.5–25.5°
α = 78.584 (6)°	µ = 0.27 mm−1
β = 82.056 (6)°	T = 296 K
γ = 68.390 (6)°	Block, yellow
V = 1375.3 (8) Å3	0.26 × 0.22 × 0.19 mm

Bruker SMART CCD area-detector diffractometer	4767 independent reflections
Radiation source: fine-focus sealed tube	3177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.934, Tmax = 0.951	k = −11→8
6863 measured reflections	l = −19→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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.310	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.2P)2 + 0.5326P] where P = (Fo2 + 2Fc2)/3
4767 reflections	(Δ/σ)max = 0.019
344 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.47 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
Cl1	1.27799 (17)	0.38291 (18)	0.06256 (10)	0.0849 (6)
Cl2	0.09798 (15)	1.31946 (16)	0.46084 (8)	0.0691 (5)
N1	0.6407 (5)	0.5253 (4)	0.3247 (2)	0.0506 (9)
H1	0.6027	0.4977	0.2889	0.061*
N2	0.7215 (4)	0.9294 (4)	0.2401 (2)	0.0402 (8)
O1	0.4493 (4)	0.6217 (4)	0.2051 (2)	0.0678 (10)
O2	0.4070 (4)	0.8552 (4)	0.1351 (2)	0.0603 (9)
C1	0.6425 (5)	0.6679 (5)	0.3057 (3)	0.0419 (10)
C2	0.7482 (5)	0.7082 (5)	0.3480 (2)	0.0421 (9)
H2A	0.8212	0.6170	0.3754	0.051*
H2B	0.6920	0.7693	0.3902	0.051*
C3	0.8308 (5)	0.7960 (4)	0.2840 (2)	0.0405 (9)
H3	0.8882	0.8310	0.3152	0.049*
C4	0.5689 (4)	0.9325 (4)	0.2344 (2)	0.0371 (9)
H4	0.5410	0.9801	0.1775	0.045*
C5	0.5638 (4)	0.7749 (4)	0.2465 (2)	0.0388 (9)
C6	0.6926 (5)	0.4163 (5)	0.3953 (3)	0.0494 (11)
C7	0.7525 (6)	0.2653 (5)	0.3857 (4)	0.0641 (13)
H7	0.7638	0.2389	0.3330	0.077*
C8	0.7951 (8)	0.1552 (7)	0.4538 (5)	0.088 (2)
H8	0.8324	0.0542	0.4472	0.106*
C9	0.7834 (9)	0.1921 (9)	0.5310 (5)	0.099 (3)
H9	0.8170	0.1170	0.5764	0.119*
C10	0.7204 (7)	0.3435 (8)	0.5415 (4)	0.0806 (18)
H10	0.7077	0.3691	0.5945	0.097*
C11	0.6774 (6)	0.4544 (6)	0.4736 (3)	0.0603 (13)
H11	0.6379	0.5553	0.4804	0.072*
C12	0.9429 (4)	0.6958 (4)	0.2266 (2)	0.0382 (9)
C13	0.9158 (5)	0.7039 (5)	0.1448 (3)	0.0454 (10)
H13	0.8267	0.7731	0.1235	0.054*
C14	1.0212 (5)	0.6088 (5)	0.0943 (3)	0.0516 (11)
H14	1.0037	0.6157	0.0390	0.062*
C15	1.1500 (5)	0.5056 (5)	0.1261 (3)	0.0503 (11)
C16	1.1801 (5)	0.4959 (5)	0.2059 (3)	0.0584 (13)
H16	1.2691	0.4253	0.2267	0.070*
C17	1.0788 (5)	0.5906 (5)	0.2554 (3)	0.0469 (10)
H17	1.1007	0.5850	0.3098	0.056*
C18	0.7597 (5)	1.0556 (4)	0.2053 (2)	0.0403 (9)
C19	0.9054 (5)	1.0534 (5)	0.2023 (3)	0.0464 (10)
H19	0.9813	0.9653	0.2230	0.056*
C20	0.9399 (6)	1.1826 (6)	0.1684 (3)	0.0581 (12)
H20	1.0386	1.1794	0.1675	0.070*
C21	0.8328 (6)	1.3126 (5)	0.1367 (3)	0.0603 (13)
H21	0.8570	1.3980	0.1146	0.072*
C22	0.6888 (6)	1.3157 (5)	0.1378 (3)	0.0541 (12)
H22	0.6148	1.4036	0.1151	0.065*
C23	0.6513 (5)	1.1904 (5)	0.1721 (3)	0.0463 (10)
H23	0.5519	1.1959	0.1731	0.056*
C24	0.4517 (4)	1.0286 (4)	0.2940 (2)	0.0362 (9)
C25	0.4924 (5)	1.0732 (5)	0.3592 (3)	0.0504 (11)
H25	0.5940	1.0438	0.3683	0.060*
C26	0.3851 (5)	1.1606 (6)	0.4112 (3)	0.0552 (12)
H26	0.4137	1.1895	0.4552	0.066*
C27	0.2356 (5)	1.2047 (5)	0.3973 (3)	0.0472 (10)
C28	0.1902 (5)	1.1639 (5)	0.3319 (3)	0.0502 (11)
H28	0.0886	1.1953	0.3223	0.060*
C29	0.2995 (5)	1.0758 (5)	0.2818 (3)	0.0462 (10)
H29	0.2705	1.0466	0.2379	0.055*
C30	0.4708 (5)	0.7404 (5)	0.1958 (3)	0.0453 (10)
C31	0.3141 (7)	0.8271 (7)	0.0817 (4)	0.0794 (18)
H31A	0.2309	0.8039	0.1148	0.095*
H31B	0.3736	0.7420	0.0538	0.095*
C32	0.2570 (9)	0.9630 (8)	0.0205 (4)	0.096 (2)
H32A	0.1894	1.0437	0.0483	0.145*
H32B	0.2042	0.9438	−0.0193	0.145*
H32C	0.3399	0.9908	−0.0079	0.145*

	U11	U22	U33	U12	U13	U23
Cl1	0.0700 (10)	0.0711 (10)	0.0914 (11)	0.0050 (7)	0.0067 (8)	−0.0297 (8)
Cl2	0.0595 (8)	0.0782 (9)	0.0611 (8)	−0.0053 (6)	0.0006 (6)	−0.0325 (7)
N1	0.065 (2)	0.0365 (19)	0.056 (2)	−0.0222 (17)	−0.0190 (18)	−0.0033 (16)
N2	0.0390 (18)	0.0324 (17)	0.049 (2)	−0.0133 (14)	−0.0061 (15)	−0.0038 (14)
O1	0.076 (2)	0.0438 (19)	0.095 (3)	−0.0248 (17)	−0.043 (2)	−0.0047 (18)
O2	0.079 (2)	0.0481 (18)	0.059 (2)	−0.0205 (17)	−0.0343 (17)	−0.0056 (15)
C1	0.049 (2)	0.037 (2)	0.044 (2)	−0.0191 (18)	−0.0037 (18)	−0.0065 (17)
C2	0.045 (2)	0.044 (2)	0.039 (2)	−0.0160 (19)	−0.0061 (17)	−0.0052 (17)
C3	0.050 (2)	0.035 (2)	0.041 (2)	−0.0171 (18)	−0.0121 (18)	−0.0060 (17)
C4	0.037 (2)	0.037 (2)	0.039 (2)	−0.0149 (17)	−0.0053 (16)	−0.0046 (16)
C5	0.038 (2)	0.036 (2)	0.044 (2)	−0.0111 (17)	−0.0048 (17)	−0.0114 (17)
C6	0.050 (3)	0.041 (2)	0.059 (3)	−0.023 (2)	−0.011 (2)	0.005 (2)
C7	0.069 (3)	0.046 (3)	0.080 (4)	−0.023 (2)	−0.012 (3)	−0.004 (2)
C8	0.085 (4)	0.051 (3)	0.126 (6)	−0.028 (3)	−0.035 (4)	0.018 (4)
C9	0.106 (5)	0.088 (5)	0.105 (6)	−0.053 (4)	−0.041 (4)	0.044 (4)
C10	0.080 (4)	0.103 (5)	0.062 (3)	−0.047 (4)	−0.009 (3)	0.011 (3)
C11	0.057 (3)	0.068 (3)	0.053 (3)	−0.026 (3)	0.007 (2)	−0.003 (2)
C12	0.038 (2)	0.031 (2)	0.044 (2)	−0.0117 (17)	−0.0122 (16)	0.0014 (16)
C13	0.044 (2)	0.041 (2)	0.045 (2)	−0.0073 (18)	−0.0086 (18)	−0.0044 (18)
C14	0.052 (3)	0.051 (3)	0.047 (2)	−0.012 (2)	−0.007 (2)	−0.010 (2)
C15	0.044 (2)	0.040 (2)	0.064 (3)	−0.014 (2)	−0.001 (2)	−0.006 (2)
C16	0.043 (3)	0.045 (3)	0.074 (3)	−0.003 (2)	−0.017 (2)	0.006 (2)
C17	0.037 (2)	0.045 (2)	0.053 (2)	−0.0064 (19)	−0.0157 (18)	0.0011 (19)
C18	0.054 (2)	0.032 (2)	0.039 (2)	−0.0166 (18)	0.0011 (17)	−0.0121 (16)
C19	0.049 (2)	0.045 (2)	0.050 (2)	−0.021 (2)	−0.0018 (19)	−0.0106 (19)
C20	0.069 (3)	0.062 (3)	0.054 (3)	−0.038 (3)	−0.006 (2)	−0.006 (2)
C21	0.071 (3)	0.046 (3)	0.067 (3)	−0.028 (3)	−0.001 (3)	−0.004 (2)
C22	0.072 (3)	0.036 (2)	0.053 (3)	−0.017 (2)	−0.005 (2)	−0.007 (2)
C23	0.054 (3)	0.040 (2)	0.045 (2)	−0.017 (2)	−0.0001 (19)	−0.0088 (18)
C24	0.042 (2)	0.0295 (19)	0.038 (2)	−0.0125 (16)	−0.0084 (16)	−0.0028 (15)
C25	0.046 (2)	0.058 (3)	0.052 (2)	−0.017 (2)	−0.0110 (19)	−0.016 (2)
C26	0.055 (3)	0.069 (3)	0.048 (3)	−0.021 (2)	−0.002 (2)	−0.027 (2)
C27	0.053 (3)	0.043 (2)	0.044 (2)	−0.013 (2)	−0.0071 (19)	−0.0077 (18)
C28	0.040 (2)	0.048 (3)	0.058 (3)	−0.005 (2)	−0.013 (2)	−0.011 (2)
C29	0.050 (2)	0.041 (2)	0.050 (2)	−0.0119 (19)	−0.0154 (19)	−0.0117 (19)
C30	0.042 (2)	0.037 (2)	0.056 (3)	−0.0080 (18)	−0.0125 (19)	−0.0126 (19)
C31	0.094 (4)	0.069 (4)	0.081 (4)	−0.018 (3)	−0.046 (3)	−0.018 (3)
C32	0.119 (6)	0.091 (5)	0.070 (4)	−0.010 (4)	−0.045 (4)	−0.020 (3)

Cl1—C15	1.747 (5)	C13—C14	1.390 (6)
Cl2—C27	1.746 (5)	C13—H13	0.9300
N1—C1	1.356 (5)	C14—C15	1.360 (6)
N1—C6	1.410 (6)	C14—H14	0.9300
N1—H1	0.8600	C15—C16	1.356 (7)
N2—C18	1.393 (5)	C16—C17	1.363 (7)
N2—C3	1.455 (5)	C16—H16	0.9300
N2—C4	1.463 (5)	C17—H17	0.9300
O1—C30	1.215 (5)	C18—C19	1.379 (6)
O2—C30	1.350 (5)	C18—C23	1.395 (6)
O2—C31	1.454 (6)	C19—C20	1.397 (6)
C1—C5	1.344 (6)	C19—H19	0.9300
C1—C2	1.499 (6)	C20—C21	1.355 (7)
C2—C3	1.534 (6)	C20—H20	0.9300
C2—H2A	0.9700	C21—C22	1.363 (7)
C2—H2B	0.9700	C21—H21	0.9300
C3—C12	1.513 (6)	C22—C23	1.379 (6)
C3—H3	0.9800	C22—H22	0.9300
C4—C5	1.513 (5)	C23—H23	0.9300
C4—C24	1.537 (5)	C24—C25	1.379 (6)
C4—H4	0.9800	C24—C29	1.386 (6)
C5—C30	1.458 (6)	C25—C26	1.377 (6)
C6—C11	1.378 (7)	C25—H25	0.9300
C6—C7	1.389 (7)	C26—C27	1.370 (6)
C7—C8	1.371 (8)	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.384 (6)
C8—C9	1.359 (11)	C28—C29	1.370 (6)
C8—H8	0.9300	C28—H28	0.9300
C9—C10	1.397 (10)	C29—H29	0.9300
C9—H9	0.9300	C31—C32	1.460 (8)
C10—C11	1.373 (8)	C31—H31A	0.9700
C10—H10	0.9300	C31—H31B	0.9700
C11—H11	0.9300	C32—H32A	0.9600
C12—C13	1.382 (6)	C32—H32B	0.9600
C12—C17	1.397 (5)	C32—H32C	0.9600
C1—N1—C6	128.7 (4)	C16—C15—Cl1	119.8 (4)
C1—N1—H1	115.7	C14—C15—Cl1	119.0 (4)
C6—N1—H1	115.7	C15—C16—C17	119.4 (4)
C18—N2—C3	120.5 (3)	C15—C16—H16	120.3
C18—N2—C4	119.7 (3)	C17—C16—H16	120.3
C3—N2—C4	119.8 (3)	C16—C17—C12	121.6 (4)
C30—O2—C31	116.2 (4)	C16—C17—H17	119.2
C5—C1—N1	124.8 (4)	C12—C17—H17	119.2
C5—C1—C2	116.4 (3)	C19—C18—N2	121.8 (4)
N1—C1—C2	118.7 (4)	C19—C18—C23	117.1 (4)
C1—C2—C3	110.2 (3)	N2—C18—C23	121.1 (4)
C1—C2—H2A	109.6	C18—C19—C20	120.5 (4)
C3—C2—H2A	109.6	C18—C19—H19	119.7
C1—C2—H2B	109.6	C20—C19—H19	119.7
C3—C2—H2B	109.6	C21—C20—C19	121.4 (5)
H2A—C2—H2B	108.1	C21—C20—H20	119.3
N2—C3—C12	113.6 (3)	C19—C20—H20	119.3
N2—C3—C2	109.8 (3)	C20—C21—C22	118.7 (4)
C12—C3—C2	111.5 (3)	C20—C21—H21	120.6
N2—C3—H3	107.2	C22—C21—H21	120.6
C12—C3—H3	107.2	C21—C22—C23	121.0 (5)
C2—C3—H3	107.2	C21—C22—H22	119.5
N2—C4—C5	111.6 (3)	C23—C22—H22	119.5
N2—C4—C24	112.6 (3)	C22—C23—C18	121.2 (4)
C5—C4—C24	111.3 (3)	C22—C23—H23	119.4
N2—C4—H4	107.0	C18—C23—H23	119.4
C5—C4—H4	107.0	C25—C24—C29	118.0 (4)
C24—C4—H4	107.0	C25—C24—C4	122.2 (3)
C1—C5—C30	120.2 (4)	C29—C24—C4	119.8 (3)
C1—C5—C4	119.7 (3)	C26—C25—C24	121.0 (4)
C30—C5—C4	120.1 (3)	C26—C25—H25	119.5
C11—C6—C7	119.5 (4)	C24—C25—H25	119.5
C11—C6—N1	122.1 (4)	C27—C26—C25	119.4 (4)
C7—C6—N1	118.3 (5)	C27—C26—H26	120.3
C8—C7—C6	120.1 (6)	C25—C26—H26	120.3
C8—C7—H7	120.0	C26—C27—C28	121.4 (4)
C6—C7—H7	120.0	C26—C27—Cl2	120.1 (3)
C9—C8—C7	120.7 (6)	C28—C27—Cl2	118.5 (3)
C9—C8—H8	119.7	C29—C28—C27	117.9 (4)
C7—C8—H8	119.7	C29—C28—H28	121.1
C8—C9—C10	119.6 (6)	C27—C28—H28	121.1
C8—C9—H9	120.2	C28—C29—C24	122.4 (4)
C10—C9—H9	120.2	C28—C29—H29	118.8
C11—C10—C9	120.0 (6)	C24—C29—H29	118.8
C11—C10—H10	120.0	O1—C30—O2	121.2 (4)
C9—C10—H10	120.0	O1—C30—C5	125.2 (4)
C10—C11—C6	120.0 (6)	O2—C30—C5	113.6 (4)
C10—C11—H11	120.0	O2—C31—C32	107.8 (5)
C6—C11—H11	120.0	O2—C31—H31A	110.1
C13—C12—C17	117.7 (4)	C32—C31—H31A	110.2
C13—C12—C3	122.1 (3)	O2—C31—H31B	110.2
C17—C12—C3	120.3 (4)	C32—C31—H31B	110.1
C12—C13—C14	120.2 (4)	H31A—C31—H31B	108.5
C12—C13—H13	119.9	C31—C32—H32A	109.5
C14—C13—H13	119.9	C31—C32—H32B	109.5
C15—C14—C13	119.8 (4)	H32A—C32—H32B	109.5
C15—C14—H14	120.1	C31—C32—H32C	109.5
C13—C14—H14	120.1	H32A—C32—H32C	109.5
C16—C15—C14	121.3 (4)	H32B—C32—H32C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.02	2.659 (5)	130
C4—H4···O2	0.98	2.30	2.761 (5)	108
C22—H22···O1i	0.93	2.69	3.287 (6)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.02	2.659 (5)	130
C4—H4⋯O2	0.98	2.30	2.761 (5)	108
C22—H22⋯O1i	0.93	2.69	3.287 (6)	122

Symmetry code: (i) .