1-Acetyl-2-r,6-c-bis­(4-chloro­phen­yl)-3-methyl-1,2,5,6-tetra­hydro­pyridin-4-yl acetate

Vimalraj, V.; Pandiarajan, K.

doi:10.1107/S1600536810047586

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3259

https://doi.org/10.1107/S1600536810047586

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1-Acetyl-2-r,6-c-bis(4-chlorophenyl)-3-methyl-1,2,5,6-tetrahydropyridin-4-yl acetate

V. Vimalraj ^a and K. Pandiarajan ^a ^*

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India
^*Correspondence e-mail: profkprajan@yahoo.co.in

(Received 17 October 2010; accepted 16 November 2010; online 20 November 2010)

In the title compound, C₂₂H₂₁Cl₂NO₃, the pyridine ring adopts a half-chair conformation and the 4-chlorophenyl groups occupy axial positions. The 4-chlorophenyl groups are almost perpendicular to the plane of the tetrahydropyridine ring forming dihedral angles 84.62 (6) and 85.55 (5)°; the dihedral angle between the two 4-chlorophenyl rings is 12.16 (4)°. The crystal structure is stabilized by intermolecular C—H⋯O interactions.

Related literature

For a related structure, see: Subha Nandhini et al. (2003 ).

Experimental

Crystal data

C₂₂H₂₁Cl₂NO₃
M_r = 418.30
Monoclinic, C c
a = 16.560 (3) Å
b = 14.809 (3) Å
c = 10.241 (2) Å
β = 124.27 (3)°
V = 2075.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.866, T_max = 0.936
13520 measured reflections
5546 independent reflections
4578 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.04
5546 reflections
256 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 2649 Friedel pairs
Flack parameter: 0.02 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.98	2.44	3.341 (3)	152
C4—H4B⋯O1ⁱⁱ	0.97	2.35	3.308 (3)	169
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Bruno et al., 2002 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810047586/pv2343sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047586/pv2343Isup2.hkl

checkCIF report

Comment top

The X-ray crystal structure determination of the title compound was undertaken to determine the effect of substitution of acetyl and acetoxy groups at positions 1 and 4, respectively, on the conformation of the tetrahydropyridine ring. The tetrahydropyridine ring adopts a half chair conformation with N1 and C3 atoms 0.324 (3) and -0.328 (3) Å, respectively, out of the basal plane formed by the remaining ring atoms (C4/C5/C6/C7) and the aryl groups occupy axial positions. The 4-chlorophenyl groups, C11–C16/Cl1 and C17–C22/Cl2, are almost perpendicular to the tetrahydropyridine ring forming dihedral angles 84.62 (6) and 85.55 (5)°, respectively; the dihedral angle between the two 4-chlorophenyl rings is 12.16 (4)°. The aryl groups take axial positions to avoid A1,3 strain. The acetoxy group O2/O3/C9/C10 is almost perpendicular (88.05 (6)°) to the tetrahydropyridine ring. The crystal structure is stabilized by intermolecular C—H···O interactions. The bond distances and angles in the title compound are comparable to a similar structure reported earlier (Subha Nandhini et al., (2003).

Related literature top

For a related structure, see: Subha Nandhini et al. (2003).

Experimental top

A mixture of 3 t-methyl-2r,6c-bis(4-chlorophenyl)-piperidin-4-one (0.01 mol) and hippuric acid in acetic anhydride (20 ml) was refluxed for about 2 h. After the completion of reaction, excess of acetic anhydride was removed by distillation and water (50 ml) was added. The title compound thus obtained as a solid product was separated and colourless crystals were grown by slow evaporation method using ethanol as solvent.

Structure description top

For a related structure, see: Subha Nandhini et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT (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 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure showing the formation of the possible three C—H···O hydrogen bonds C4—H4B···O1ⁱ, C3—H3···O3ⁱⁱ and C21—H21···O1ⁱⁱⁱ [symmetry code: (i) x, -y+1, z+1/2, (ii) x+1/2, -y+1/2, z+1/2 /and (iii) x,-y+1,+z-1/2] with in the unit cell.

1-Acetyl-2-r,6-c-bis(4-chlorophenyl)-3-methyl-1,2,5,6-tetrahydropyridin-4-yl acetate top

Crystal data top

C₂₂H₂₁Cl₂NO₃	F(000) = 872
M_r = 418.30	D_x = 1.339 Mg m⁻³
Monoclinic, Cc	Melting point: 411 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 16.560 (3) Å	Cell parameters from 6663 reflections
b = 14.809 (3) Å	θ = 2.8–59.2°
c = 10.241 (2) Å	µ = 0.34 mm⁻¹
β = 124.27 (3)°	T = 293 K
V = 2075.5 (10) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5546 independent reflections
Radiation source: fine-focus sealed tube	4578 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and φ scans	θ_max = 29.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −22→22
T_min = 0.866, T_max = 0.936	k = −20→20
13520 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0528P)² + 0.2729P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.011
5546 reflections	Δρ_max = 0.27 e Å⁻³
256 parameters	Δρ_min = −0.17 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 2649 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

Crystal data top

C₂₂H₂₁Cl₂NO₃	V = 2075.5 (10) Å³
M_r = 418.30	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 16.560 (3) Å	µ = 0.34 mm⁻¹
b = 14.809 (3) Å	T = 293 K
c = 10.241 (2) Å	0.30 × 0.25 × 0.20 mm
β = 124.27 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5546 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4578 reflections with I > 2σ(I)
T_min = 0.866, T_max = 0.936	R_int = 0.020
13520 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.27 e Å⁻³
S = 1.04	Δρ_min = −0.17 e Å⁻³
5546 reflections	Absolute structure: Flack (1983), 2649 Friedel pairs
256 parameters	Absolute structure parameter: 0.02 (5)
2 restraints

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
Cl2	0.12844 (5)	0.18128 (4)	−0.47636 (7)	0.07210 (17)
Cl1	0.25477 (6)	−0.00598 (5)	−0.08332 (9)	0.0858 (2)
O2	0.03552 (10)	0.37134 (10)	0.21164 (17)	0.0576 (4)
N1	0.26481 (10)	0.40891 (9)	0.16833 (17)	0.0389 (3)
C2	0.33771 (12)	0.46887 (12)	0.2128 (2)	0.0478 (4)
O1	0.32636 (10)	0.53254 (10)	0.1281 (2)	0.0664 (4)
C20	0.13277 (14)	0.25613 (13)	−0.3423 (2)	0.0488 (4)
C17	0.14951 (12)	0.36840 (12)	−0.1132 (2)	0.0395 (3)
O3	−0.01433 (13)	0.24011 (13)	0.0838 (2)	0.0784 (5)
C19	0.08085 (13)	0.23746 (14)	−0.2795 (2)	0.0496 (4)
H19	0.0403	0.1871	−0.3131	0.059*
C3	0.27461 (12)	0.33000 (11)	0.2627 (2)	0.0398 (3)
H3	0.3404	0.3321	0.3604	0.048*
C7	0.16844 (11)	0.42629 (12)	0.0235 (2)	0.0398 (3)
H7	0.1680	0.4894	−0.0058	0.048*
C4	0.20259 (13)	0.33908 (12)	0.3092 (2)	0.0457 (4)
H4A	0.1924	0.2803	0.3393	0.055*
H4B	0.2301	0.3785	0.4003	0.055*
C11	0.26760 (11)	0.24311 (10)	0.17759 (19)	0.0391 (3)
C18	0.08892 (12)	0.29388 (13)	−0.1653 (2)	0.0442 (4)
H18	0.0531	0.2815	−0.1229	0.053*
C21	0.19096 (16)	0.33134 (13)	−0.2975 (3)	0.0539 (5)
H21	0.2246	0.3444	−0.3435	0.065*
C16	0.32496 (13)	0.23387 (13)	0.1197 (2)	0.0492 (4)
H16	0.3668	0.2807	0.1349	0.059*
C15	0.32233 (15)	0.15862 (14)	0.0411 (3)	0.0557 (5)
H15	0.3611	0.1545	0.0022	0.067*
C5	0.10804 (13)	0.37564 (13)	0.1803 (2)	0.0446 (4)
C12	0.20837 (14)	0.17175 (12)	0.1571 (2)	0.0462 (4)
H12	0.1699	0.1757	0.1966	0.055*
C22	0.19884 (14)	0.38696 (13)	−0.1840 (2)	0.0497 (4)
H22	0.2380	0.4382	−0.1537	0.060*
C6	0.08920 (12)	0.41668 (12)	0.0530 (2)	0.0437 (4)
C14	0.26133 (15)	0.08872 (13)	0.0203 (2)	0.0518 (4)
C13	0.20498 (15)	0.09451 (14)	0.0792 (2)	0.0536 (4)
H13	0.1648	0.0467	0.0666	0.064*
C9	−0.02127 (14)	0.29704 (16)	0.1591 (3)	0.0569 (5)
C8	−0.00692 (15)	0.45758 (17)	−0.0687 (3)	0.0646 (5)
H8A	−0.0584	0.4164	−0.0930	0.097*
H8B	−0.0091	0.4697	−0.1627	0.097*
H8C	−0.0152	0.5130	−0.0289	0.097*
C1	0.43369 (16)	0.45659 (18)	0.3692 (3)	0.0773 (7)
H1A	0.4787	0.5024	0.3819	0.116*
H1B	0.4598	0.3981	0.3727	0.116*
H1C	0.4239	0.4615	0.4528	0.116*
C10	−0.0915 (2)	0.2967 (2)	0.2046 (4)	0.0833 (8)
H10A	−0.1459	0.3350	0.1341	0.125*
H10B	−0.0599	0.3187	0.3108	0.125*
H10C	−0.1143	0.2363	0.1985	0.125*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.0966 (4)	0.0705 (3)	0.0709 (3)	−0.0064 (3)	0.0603 (3)	−0.0127 (3)
Cl1	0.1101 (5)	0.0630 (3)	0.0896 (4)	0.0059 (3)	0.0595 (4)	−0.0197 (3)
O2	0.0616 (8)	0.0641 (9)	0.0680 (9)	−0.0104 (7)	0.0490 (8)	−0.0149 (7)
N1	0.0354 (6)	0.0352 (6)	0.0391 (7)	−0.0014 (6)	0.0166 (6)	0.0038 (6)
C2	0.0403 (9)	0.0400 (9)	0.0554 (11)	−0.0051 (7)	0.0222 (9)	−0.0003 (8)
O1	0.0557 (8)	0.0515 (8)	0.0809 (11)	−0.0070 (6)	0.0317 (8)	0.0186 (8)
C20	0.0537 (10)	0.0509 (10)	0.0419 (9)	0.0050 (9)	0.0269 (9)	0.0031 (8)
C17	0.0355 (7)	0.0441 (9)	0.0363 (8)	0.0034 (7)	0.0186 (7)	0.0069 (7)
O3	0.0740 (10)	0.0830 (11)	0.0867 (12)	−0.0323 (9)	0.0504 (10)	−0.0365 (10)
C19	0.0419 (9)	0.0561 (11)	0.0468 (10)	−0.0072 (8)	0.0226 (8)	−0.0041 (8)
C3	0.0401 (8)	0.0393 (8)	0.0349 (8)	−0.0014 (7)	0.0179 (7)	0.0031 (6)
C7	0.0383 (8)	0.0390 (8)	0.0402 (9)	0.0005 (7)	0.0211 (8)	0.0046 (7)
C4	0.0556 (10)	0.0439 (9)	0.0417 (9)	−0.0039 (8)	0.0299 (9)	−0.0022 (7)
C11	0.0364 (8)	0.0363 (8)	0.0362 (8)	0.0031 (6)	0.0154 (7)	0.0054 (6)
C18	0.0396 (8)	0.0535 (10)	0.0425 (9)	−0.0022 (7)	0.0249 (8)	0.0005 (8)
C21	0.0649 (11)	0.0550 (11)	0.0584 (11)	0.0003 (9)	0.0447 (10)	0.0088 (9)
C16	0.0416 (9)	0.0492 (9)	0.0576 (11)	0.0014 (8)	0.0284 (9)	0.0054 (8)
C15	0.0552 (11)	0.0560 (11)	0.0627 (12)	0.0108 (9)	0.0372 (10)	0.0038 (9)
C5	0.0480 (9)	0.0459 (9)	0.0488 (10)	−0.0057 (7)	0.0326 (8)	−0.0114 (8)
C12	0.0522 (9)	0.0416 (9)	0.0519 (10)	0.0010 (8)	0.0335 (9)	0.0043 (8)
C22	0.0562 (10)	0.0459 (10)	0.0548 (11)	−0.0036 (8)	0.0360 (10)	0.0056 (8)
C6	0.0387 (8)	0.0449 (9)	0.0479 (10)	−0.0021 (7)	0.0246 (8)	−0.0063 (8)
C14	0.0596 (11)	0.0439 (9)	0.0473 (10)	0.0126 (8)	0.0273 (9)	0.0026 (8)
C13	0.0600 (11)	0.0434 (10)	0.0539 (11)	−0.0042 (8)	0.0299 (10)	−0.0004 (8)
C9	0.0465 (10)	0.0690 (13)	0.0547 (11)	−0.0071 (9)	0.0283 (10)	−0.0039 (10)
C8	0.0464 (10)	0.0793 (15)	0.0663 (13)	0.0130 (10)	0.0305 (10)	0.0061 (11)
C1	0.0444 (11)	0.0672 (15)	0.0794 (17)	−0.0147 (10)	0.0100 (11)	0.0094 (12)
C10	0.0653 (14)	0.105 (2)	0.100 (2)	−0.0069 (15)	0.0590 (16)	0.0042 (17)

Geometric parameters (Å, º) top

Cl2—C20	1.7343 (19)	C11—C16	1.381 (2)
Cl1—C14	1.725 (2)	C18—H18	0.9300
O2—C9	1.347 (3)	C21—C22	1.369 (3)
O2—C5	1.409 (2)	C21—H21	0.9300
N1—C2	1.354 (2)	C16—C15	1.361 (3)
N1—C7	1.465 (2)	C16—H16	0.9300
N1—C3	1.466 (2)	C15—C14	1.377 (3)
C2—O1	1.222 (2)	C15—H15	0.9300
C2—C1	1.503 (3)	C5—C6	1.307 (3)
C20—C19	1.361 (2)	C12—C13	1.378 (3)
C20—C21	1.372 (3)	C12—H12	0.9300
C17—C18	1.381 (3)	C22—H22	0.9300
C17—C22	1.391 (2)	C6—C8	1.490 (3)
C17—C7	1.516 (2)	C14—C13	1.369 (3)
O3—C9	1.191 (3)	C13—H13	0.9300
C19—C18	1.381 (3)	C9—C10	1.475 (3)
C19—H19	0.9300	C8—H8A	0.9600
C3—C4	1.519 (2)	C8—H8B	0.9600
C3—C11	1.521 (2)	C8—H8C	0.9600
C3—H3	0.9800	C1—H1A	0.9600
C7—C6	1.510 (2)	C1—H1B	0.9600
C7—H7	0.9800	C1—H1C	0.9600
C4—C5	1.470 (3)	C10—H10A	0.9600
C4—H4A	0.9700	C10—H10B	0.9600
C4—H4B	0.9700	C10—H10C	0.9600
C11—C12	1.375 (2)

C9—O2—C5	116.06 (15)	C15—C16—H16	118.9
C2—N1—C7	118.79 (14)	C11—C16—H16	118.9
C2—N1—C3	123.66 (14)	C16—C15—C14	118.94 (18)
C7—N1—C3	117.42 (13)	C16—C15—H15	120.5
O1—C2—N1	121.05 (17)	C14—C15—H15	120.5
O1—C2—C1	119.84 (18)	C6—C5—O2	119.56 (17)
N1—C2—C1	119.11 (17)	C6—C5—C4	127.06 (15)
C19—C20—C21	121.22 (17)	O2—C5—C4	113.09 (16)
C19—C20—Cl2	119.27 (15)	C11—C12—C13	121.28 (17)
C21—C20—Cl2	119.48 (14)	C11—C12—H12	119.4
C18—C17—C22	117.96 (17)	C13—C12—H12	119.4
C18—C17—C7	122.41 (14)	C21—C22—C17	121.33 (18)
C22—C17—C7	119.52 (16)	C21—C22—H22	119.3
C20—C19—C18	119.45 (17)	C17—C22—H22	119.3
C20—C19—H19	120.3	C5—C6—C8	124.46 (16)
C18—C19—H19	120.3	C5—C6—C7	119.81 (15)
N1—C3—C4	108.74 (14)	C8—C6—C7	115.73 (16)
N1—C3—C11	110.61 (13)	C13—C14—C15	120.48 (18)
C4—C3—C11	115.75 (14)	C13—C14—Cl1	119.96 (17)
N1—C3—H3	107.1	C15—C14—Cl1	119.55 (15)
C4—C3—H3	107.1	C14—C13—C12	119.44 (18)
C11—C3—H3	107.1	C14—C13—H13	120.3
N1—C7—C6	110.78 (13)	C12—C13—H13	120.3
N1—C7—C17	112.11 (14)	O3—C9—O2	122.43 (18)
C6—C7—C17	112.35 (14)	O3—C9—C10	125.6 (2)
N1—C7—H7	107.1	O2—C9—C10	111.9 (2)
C6—C7—H7	107.1	C6—C8—H8A	109.5
C17—C7—H7	107.1	C6—C8—H8B	109.5
C5—C4—C3	112.22 (14)	H8A—C8—H8B	109.5
C5—C4—H4A	109.2	C6—C8—H8C	109.5
C3—C4—H4A	109.2	H8A—C8—H8C	109.5
C5—C4—H4B	109.2	H8B—C8—H8C	109.5
C3—C4—H4B	109.2	C2—C1—H1A	109.5
H4A—C4—H4B	107.9	C2—C1—H1B	109.5
C12—C11—C16	117.53 (16)	H1A—C1—H1B	109.5
C12—C11—C3	123.71 (15)	C2—C1—H1C	109.5
C16—C11—C3	118.74 (15)	H1A—C1—H1C	109.5
C17—C18—C19	120.89 (15)	H1B—C1—H1C	109.5
C17—C18—H18	119.6	C9—C10—H10A	109.5
C19—C18—H18	119.6	C9—C10—H10B	109.5
C22—C21—C20	119.07 (16)	H10A—C10—H10B	109.5
C22—C21—H21	120.5	C9—C10—H10C	109.5
C20—C21—H21	120.5	H10A—C10—H10C	109.5
C15—C16—C11	122.30 (17)	H10B—C10—H10C	109.5

C7—N1—C2—O1	−5.9 (3)	Cl2—C20—C21—C22	−175.81 (16)
C3—N1—C2—O1	178.46 (18)	C12—C11—C16—C15	1.7 (3)
C7—N1—C2—C1	173.89 (19)	C3—C11—C16—C15	−179.45 (18)
C3—N1—C2—C1	−1.8 (3)	C11—C16—C15—C14	−0.8 (3)
C21—C20—C19—C18	−1.8 (3)	C9—O2—C5—C6	93.2 (2)
Cl2—C20—C19—C18	175.93 (15)	C9—O2—C5—C4	−92.5 (2)
C2—N1—C3—C4	117.77 (18)	C3—C4—C5—C6	−15.7 (3)
C7—N1—C3—C4	−57.97 (18)	C3—C4—C5—O2	170.56 (14)
C2—N1—C3—C11	−114.08 (18)	C16—C11—C12—C13	−1.2 (3)
C7—N1—C3—C11	70.18 (18)	C3—C11—C12—C13	−179.91 (18)
C2—N1—C7—C6	−130.70 (16)	C20—C21—C22—C17	0.3 (3)
C3—N1—C7—C6	45.2 (2)	C18—C17—C22—C21	−2.6 (3)
C2—N1—C7—C17	102.91 (18)	C7—C17—C22—C21	173.71 (17)
C3—N1—C7—C17	−81.14 (17)	O2—C5—C6—C8	−2.5 (3)
C18—C17—C7—N1	103.99 (18)	C4—C5—C6—C8	−175.8 (2)
C22—C17—C7—N1	−72.1 (2)	O2—C5—C6—C7	176.44 (15)
C18—C17—C7—C6	−21.5 (2)	C4—C5—C6—C7	3.1 (3)
C22—C17—C7—C6	162.36 (16)	N1—C7—C6—C5	−16.0 (2)
N1—C3—C4—C5	39.76 (19)	C17—C7—C6—C5	110.29 (17)
C11—C3—C4—C5	−85.43 (19)	N1—C7—C6—C8	163.06 (16)
N1—C3—C11—C12	−131.11 (17)	C17—C7—C6—C8	−70.7 (2)
C4—C3—C11—C12	−6.9 (2)	C16—C15—C14—C13	−0.7 (3)
N1—C3—C11—C16	50.2 (2)	C16—C15—C14—Cl1	178.36 (16)
C4—C3—C11—C16	174.38 (15)	C15—C14—C13—C12	1.2 (3)
C22—C17—C18—C19	2.7 (3)	Cl1—C14—C13—C12	−177.82 (16)
C7—C17—C18—C19	−173.48 (16)	C11—C12—C13—C14	−0.3 (3)
C20—C19—C18—C17	−0.6 (3)	C5—O2—C9—O3	−3.6 (3)
C19—C20—C21—C22	1.9 (3)	C5—O2—C9—C10	177.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.98	2.44	3.341 (3)	152
C4—H4B···O1ⁱⁱ	0.97	2.35	3.308 (3)	169
C7—H7···O1	0.98	2.26	2.701 (2)	106

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁Cl₂NO₃
M_r	418.30
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	16.560 (3), 14.809 (3), 10.241 (2)
β (°)	124.27 (3)
V (Å³)	2075.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.866, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	13520, 5546, 4578
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.696

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.04
No. of reflections	5546
No. of parameters	256
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.17
Absolute structure	Flack (1983), 2649 Friedel pairs
Absolute structure parameter	0.02 (5)

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.98	2.44	3.341 (3)	152
C4—H4B···O1ⁱⁱ	0.97	2.35	3.308 (3)	169
C7—H7···O1	0.98	2.26	2.701 (2)	106

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, −y+1, z+1/2.

Acknowledgements

The authors are grateful to Dr Babu Varghese, Senior Scientist, Indian Institute of Technology Madras, for his valuable suggestions and for the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389–397. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Subha Nandhini, M., Vijayakumar, V., Mostad, A., Sundaravadivelu, M. & Natarajan, S. (2003). Acta Cryst. E59, o1672–o1674. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

1-Acetyl-2-r,6-c-bis­­(4-chloro­phen­yl)-3-methyl-1,2,5,6-tetra­hydro­pyridin-4-yl acetate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Acetyl-2-r,6-c-bis(4-chlorophenyl)-3-methyl-1,2,5,6-tetrahydropyridin-4-yl acetate