Ethyl 4-anilino-2,6-bis­(4-chloro­phen­yl)-1-phenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

Yu, J.; Tang, S.; Zeng, J.; Yan, Z.

doi:10.1107/S1600536813013573

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o947-o948

doi:10.1107/S1600536813013573

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Ethyl 4-anilino-2,6-bis(4-chlorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Jianfeng Yu,^a Shiming Tang,^a Jingbin Zeng ^a and Zifeng Yan ^b ^*

^aDepartment of Chemistry, College of Science, China University of Petroleum, Qingdao 266555, People's Republic of China, and ^bState Key Laboratory of Heavy Oil Processing, China University of Petroleum, Qingdao 266555, People's Republic of China
^*Correspondence e-mail: zfyancat@163.com

(Received 6 May 2013; accepted 17 May 2013; online 22 May 2013)

The title compound, C₃₂H₂₈Cl₂N₂O₂, was synthesized by a multicomponent reaction of 4-chlorobenzaldehyde, aniline and ethyl acetoacetate. The central 1,2,5,6-tetrahydropyridine ring exhibits a distorted boat conformation and the two chlorophenyl rings attached to the central ring at positions 2 and 6 are oriented in opposite directions. The two O atoms of the ethoxycarbonyl group are involved in intramolecular N—H⋯O and C—H⋯O hydrogen bonds. In the crystal, weak C—H⋯O hydrogen bonds link molecules 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_r = 543.46
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.070
wR(F²) = 0.310
S = 1.08
4767 reflections
344 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013573/cv5409sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813013573/cv5409Isup3.cml

checkCIF report

Comment top

Functionalized piperidines occur with great regularity in the natural product arena and as important units in pharmaceuticals (Viegas et al., 2004; Kobayashi et al., 1999). As a continuation of structural study of functionalized piperidines (Brahmachari et al., 2012; Khan et al., 2008), herewith we present the title compound.

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in anti-ethyl 4-anilino-1,2,6-triphenyl-1,2,5,6-tetrahydro-3- pyridinecarboxylate and ethyl 4-anilino-1,2,6-triphenyl-1,2,5,6-tetrahydropyridine-3-carboxylate (Khan et al., 2008; Brahmachari et al., 2012). The molecule of (I) contains one 1,2,5,6-tetrahydropyridine ring, ester group and four benzene rings. The central 1,2,5,6-tetrahydropyridine ring exhibits a distorted boat conformation, with the benzene rings attached to the C1, C3, N2 and C4 atoms. Two p-chorobenzene groups lie in the trans- position of the boat. The dihedral angles between the phenyl ring C6—C11 and phenyl rings C12—C17, C18—C23 and C24—C29 are 39.87 (1)°,85.04 (1)° and 65.60 (1)°, respectively. Two O atoms of the ethoxycarbonyl group are involved in intramolecular hydrogen bonds, N—H···O and C—H···O (Table 1), respectively.

In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules related by translation along the b axis into chains.

Related literature top

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 top

A 50 ml flask was charged with a magnetic stir bar, p-chlorobenzaldehyde (5 mmol), ethylacetoacetate (2.5 mmol) and bismuth nitrate (0.005 mmol) in 10 ml e thanol; the mixture was then started to stir at room temperature. After 1 h min, p-chlorobenzaldehyde (5 mmol) was added to the reaction mixture and stirring was continued up to completion of the reaction as monitored by TLC. After completion of the reaction, a thick precipitate was obtained. The solid was dissolved in hot ethyl acetate-ethanol mixture, the filtrate on standing afforded crystals of the pure product.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 30% probabilty displacement ellipsoids. H atoms omitted for clarity.

Ethyl 4-anilino-2,6-bis(4-chlorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate top

Crystal data top

C₃₂H₂₈Cl₂N₂O₂	Z = 2
M_r = 543.46	F(000) = 568
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	4767 independent reflections
Radiation source: fine-focus sealed tube	3177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 25.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.934, T_max = 0.951	k = −11→8
6863 measured reflections	l = −19→15

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.310	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.2P)² + 0.5326P] where P = (F_o² + 2F_c²)/3
4767 reflections	(Δ/σ)_max = 0.019
344 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₃₂H₂₈Cl₂N₂O₂	γ = 68.390 (6)°
M_r = 543.46	V = 1375.3 (8) Å³
Triclinic, P1	Z = 2
a = 9.559 (4) Å	Mo Kα radiation
b = 9.656 (3) Å	µ = 0.27 mm⁻¹
c = 16.392 (6) Å	T = 296 K
α = 78.584 (6)°	0.26 × 0.22 × 0.19 mm
β = 82.056 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4767 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3177 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.951	R_int = 0.022
6863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.310	H-atom parameters constrained
S = 1.08	Δρ_max = 0.49 e Å⁻³
4767 reflections	Δρ_min = −0.47 e Å⁻³
344 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₂₈Cl₂N₂O₂
M_r	543.46
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.559 (4), 9.656 (3), 16.392 (6)
α, β, γ (°)	78.584 (6), 82.056 (6), 68.390 (6)
V (Å³)	1375.3 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.26 × 0.22 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.934, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	6863, 4767, 3177
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.310, 1.08
No. of reflections	4767
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.47

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Acknowledgements

The authors gratefully acknowledge financial support by the Fundamental Research Funds for the Central Universities (grant No. 12CX04091A).

References

Brahmachari, G. & Das, S. (2012). Tetrahedron Lett. 53, 1479–1484. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khan, A. T., Parvin, T. & Choudhury, L. H. (2008). J. Org. Chem. 73, 8398–8402. Web of Science CSD CrossRef PubMed CAS Google Scholar
Kobayashi, S., Ueno, M., Suzuki, R., Ishitani, H., Kim, H. S. & Wataya, Y. (1999). J. Org. Chem. 64, 6833–6841. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Viegas, C., Bolzani, J. V. S., Furlan, M., Barreiro, E. J., Young, M. C. M., Tomazela, D. & Eberlin, M. N. (2004). J. Nat. Prod. 67, 908–910. Web of Science PubMed CAS Google Scholar

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Volume 69| Part 6| June 2013| Pages o947-o948

doi:10.1107/S1600536813013573

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 4-anilino-2,6-bis­­(4-chloro­phen­yl)-1-phenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

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Experimental

Crystal data

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Supporting information

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organic compounds

Ethyl 4-anilino-2,6-bis(4-chlorophenyl)-1-phenyl-1,2,5,6-tetrahydropyridine-3-carboxylate