1-(2-Chloro­acet­yl)-3-methyl-2,6-diphenyl­piperidin-4-one

Khan, F.N.; Nithya, P.; Krishna Kumar, V.; Hathwar, V.R.; Ng, S.W.

doi:10.1107/S1600536809045358

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2985

doi:10.1107/S1600536809045358

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1-(2-Chloroacetyl)-3-methyl-2,6-diphenylpiperidin-4-one

F. Nawaz Khan,^a P. Nithya,^a V. Krishna Kumar,^a Venkatesha R. Hathwar ^b and Seik Weng Ng ^c ^*

^aChemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 October 2009; accepted 29 October 2009; online 4 November 2009)

The asymmetric unit of the title compound, C₂₀H₂₀ClNO₂, contains two crystallographically independent molecules of similar geometry. The piperidine ring adopts a distorted boat conformation in both molecules, in which the N atom assumes an almost planar configuration.

Related literature

For the crystal structure of 3,5-dimethyl-bis(2-methoxyphenyl)piperidin-4-one, see: Parthiban et al. (2008 ).

Experimental

Crystal data

C₂₀H₂₀ClNO₂
M_r = 341.82
Monoclinic, C c
a = 31.026 (6) Å
b = 12.417 (2) Å
c = 9.3209 (17) Å
β = 101.423 (4)°
V = 3519.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 290 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.945, T_max = 0.956
14797 measured reflections
7013 independent reflections
4933 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.094
S = 1.05
7013 reflections
435 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 3002 Friedel pairs
Flack parameter: 0.04 (5)

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045358/ci2956sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045358/ci2956Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of 3,5-dimethyl-bis(2-methoxyphenyl)piperidin-4-one, see: Parthiban et al. (2008).

Experimental top

To a solution of 3-methyl-2,6-diphenylpiperidin-4-one (0.005 mol) and triethylamine (0.005 mol) dissolved in benzene (50 ml), chloroacetyl chloride (0.005 mol) dissolved in benzene (10 ml) was added. The mixture was stirred for an hour. The mixture was then poured into water and the organic product extracted with ether. The ether phase was washed with 3% sodium bicarbonate solution and then dried over anhydrous sodium sulfate. The compound was purified by recrystallization from ethanol.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C₂₀H₂₀ClNO₂ at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.

1-(2-Chloroacetyl)-3-methyl-2,6-diphenylpiperidin-4-one top

Crystal data top

C₂₀H₂₀ClNO₂	F(000) = 1440
M_r = 341.82	D_x = 1.290 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1325 reflections
a = 31.026 (6) Å	θ = 3.0–20.7°
b = 12.417 (2) Å	µ = 0.23 mm⁻¹
c = 9.3209 (17) Å	T = 290 K
β = 101.423 (4)°	Block, colourless
V = 3519.8 (11) Å³	0.25 × 0.23 × 0.20 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	7013 independent reflections
Radiation source: fine-focus sealed tube	4933 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −38→40
T_min = 0.945, T_max = 0.956	k = −16→16
14797 measured reflections	l = −11→12

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0334P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
7013 reflections	Δρ_max = 0.31 e Å⁻³
435 parameters	Δρ_min = −0.14 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 3002 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (5)

Crystal data top

C₂₀H₂₀ClNO₂	V = 3519.8 (11) Å³
M_r = 341.82	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 31.026 (6) Å	µ = 0.23 mm⁻¹
b = 12.417 (2) Å	T = 290 K
c = 9.3209 (17) Å	0.25 × 0.23 × 0.20 mm
β = 101.423 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7013 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4933 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.956	R_int = 0.036
14797 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.31 e Å⁻³
S = 1.05	Δρ_min = −0.14 e Å⁻³
7013 reflections	Absolute structure: Flack (1983), 3002 Friedel pairs
435 parameters	Absolute structure parameter: 0.04 (5)
2 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.50000 (3)	0.64105 (6)	0.50836 (9)	0.0634 (2)
Cl2	0.41803 (3)	0.49823 (7)	0.15694 (9)	0.0608 (2)
O1	0.63439 (8)	0.1780 (2)	0.3091 (3)	0.0758 (7)
O2	0.57673 (8)	0.53213 (18)	0.6705 (3)	0.0685 (7)
O3	0.22780 (8)	0.6049 (2)	0.4959 (3)	0.0728 (7)
O4	0.32828 (7)	0.55176 (18)	0.0346 (2)	0.0622 (6)
N1	0.57108 (8)	0.3715 (2)	0.5510 (2)	0.0430 (6)
N2	0.30973 (8)	0.64746 (17)	0.2214 (2)	0.0405 (6)
C1	0.61735 (10)	0.2246 (3)	0.3972 (3)	0.0510 (8)
C2	0.63947 (11)	0.3156 (3)	0.4873 (4)	0.0598 (9)
H2A	0.6395	0.3782	0.4251	0.072*
H2B	0.6698	0.2961	0.5258	0.072*
C3	0.61746 (10)	0.3449 (3)	0.6139 (3)	0.0501 (8)
H3	0.6313	0.4118	0.6560	0.060*
C4	0.54533 (10)	0.2968 (2)	0.4414 (3)	0.0422 (7)
H4	0.5391	0.3344	0.3471	0.051*
C5	0.57193 (10)	0.1944 (2)	0.4222 (3)	0.0470 (8)
H5	0.5761	0.1545	0.5146	0.056*
C6	0.62226 (10)	0.2644 (3)	0.7379 (3)	0.0472 (8)
C7	0.64743 (11)	0.1717 (3)	0.7463 (4)	0.0602 (9)
H7	0.6631	0.1574	0.6730	0.072*
C8	0.64984 (12)	0.1004 (3)	0.8605 (4)	0.0675 (10)
H8	0.6670	0.0388	0.8640	0.081*
C9	0.62698 (13)	0.1204 (3)	0.9686 (4)	0.0695 (10)
H9	0.6279	0.0713	1.0446	0.083*
C10	0.60264 (12)	0.2128 (3)	0.9652 (4)	0.0698 (11)
H10	0.5875	0.2274	1.0397	0.084*
C11	0.60076 (11)	0.2835 (3)	0.8510 (3)	0.0598 (9)
H11	0.5844	0.3464	0.8501	0.072*
C12	0.50134 (10)	0.2664 (2)	0.4800 (3)	0.0443 (7)
C13	0.49875 (13)	0.2290 (3)	0.6171 (4)	0.0621 (10)
H13	0.5242	0.2204	0.6880	0.074*
C14	0.45792 (15)	0.2039 (3)	0.6495 (4)	0.0744 (12)
H14	0.4562	0.1790	0.7423	0.089*
C15	0.42043 (14)	0.2160 (3)	0.5452 (5)	0.0713 (11)
H15	0.3932	0.1996	0.5672	0.086*
C16	0.42293 (12)	0.2519 (3)	0.4098 (5)	0.0649 (9)
H16	0.3974	0.2601	0.3392	0.078*
C17	0.46276 (10)	0.2760 (2)	0.3765 (4)	0.0524 (8)
H17	0.4640	0.2993	0.2826	0.063*
C18	0.55669 (10)	0.4715 (2)	0.5775 (4)	0.0480 (8)
C19	0.51356 (11)	0.5052 (2)	0.4795 (4)	0.0570 (9)
H19A	0.4902	0.4589	0.4985	0.068*
H19B	0.5158	0.4958	0.3780	0.068*
C20	0.54732 (12)	0.1207 (3)	0.3038 (4)	0.0682 (10)
H20A	0.5666	0.0647	0.2840	0.102*
H20B	0.5371	0.1616	0.2163	0.102*
H20C	0.5226	0.0893	0.3363	0.102*
C21	0.32251 (10)	0.6907 (2)	0.3728 (3)	0.0411 (7)
H21	0.3375	0.6327	0.4347	0.049*
C22	0.28172 (11)	0.7229 (3)	0.4345 (3)	0.0492 (8)
H22	0.2696	0.7884	0.3833	0.059*
C23	0.24657 (10)	0.6372 (3)	0.4037 (4)	0.0510 (8)
C24	0.23644 (11)	0.5946 (3)	0.2506 (3)	0.0520 (8)
H24A	0.2054	0.6053	0.2109	0.062*
H24B	0.2420	0.5177	0.2534	0.062*
C25	0.26308 (10)	0.6470 (2)	0.1472 (3)	0.0446 (7)
H25	0.2611	0.5977	0.0641	0.054*
C26	0.24783 (10)	0.7553 (2)	0.0823 (3)	0.0470 (8)
C27	0.21257 (12)	0.8110 (3)	0.1142 (4)	0.0613 (9)
H27	0.1970	0.7822	0.1806	0.074*
C28	0.20001 (14)	0.9089 (3)	0.0493 (4)	0.0825 (12)
H28	0.1762	0.9455	0.0730	0.099*
C29	0.22233 (16)	0.9526 (3)	−0.0500 (5)	0.0910 (14)
H29	0.2141	1.0192	−0.0923	0.109*
C30	0.25681 (15)	0.8972 (4)	−0.0860 (4)	0.0827 (12)
H30	0.2719	0.9256	−0.1543	0.099*
C31	0.26915 (12)	0.7997 (3)	−0.0212 (4)	0.0644 (10)
H31	0.2924	0.7624	−0.0474	0.077*
C32	0.35415 (10)	0.7850 (2)	0.3844 (3)	0.0427 (7)
C33	0.39264 (11)	0.7851 (3)	0.4903 (3)	0.0525 (8)
H33	0.3992	0.7256	0.5513	0.063*
C34	0.42113 (12)	0.8708 (3)	0.5068 (4)	0.0656 (10)
H34	0.4466	0.8688	0.5787	0.079*
C35	0.41234 (14)	0.9586 (3)	0.4187 (5)	0.0741 (12)
H35	0.4318	1.0164	0.4298	0.089*
C36	0.37464 (15)	0.9612 (3)	0.3134 (5)	0.0749 (11)
H36	0.3686	1.0211	0.2528	0.090*
C37	0.34551 (13)	0.8754 (2)	0.2963 (4)	0.0597 (9)
H37	0.3199	0.8785	0.2249	0.072*
C38	0.33837 (10)	0.5885 (2)	0.1586 (3)	0.0439 (7)
C39	0.38335 (10)	0.5695 (3)	0.2533 (3)	0.0506 (8)
H39A	0.3802	0.5288	0.3395	0.061*
H39B	0.3967	0.6382	0.2856	0.061*
C40	0.29396 (13)	0.7496 (4)	0.5967 (4)	0.0788 (12)
H40A	0.3109	0.6916	0.6477	0.118*
H40B	0.2677	0.7594	0.6349	0.118*
H40C	0.3110	0.8146	0.6098	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0701 (6)	0.0429 (4)	0.0813 (6)	0.0046 (4)	0.0246 (5)	0.0002 (4)
Cl2	0.0606 (5)	0.0579 (5)	0.0667 (5)	0.0203 (4)	0.0193 (4)	−0.0063 (4)
O1	0.0668 (16)	0.109 (2)	0.0558 (15)	0.0238 (15)	0.0222 (13)	−0.0105 (14)
O2	0.0717 (17)	0.0582 (14)	0.0703 (16)	−0.0018 (12)	0.0007 (14)	−0.0201 (13)
O3	0.0627 (17)	0.100 (2)	0.0621 (16)	−0.0086 (14)	0.0277 (14)	0.0125 (14)
O4	0.0593 (15)	0.0758 (15)	0.0515 (15)	0.0092 (12)	0.0109 (12)	−0.0225 (13)
N1	0.0408 (15)	0.0484 (15)	0.0405 (15)	0.0006 (12)	0.0094 (12)	−0.0013 (11)
N2	0.0452 (15)	0.0410 (13)	0.0375 (15)	0.0034 (12)	0.0134 (13)	−0.0056 (11)
C1	0.050 (2)	0.068 (2)	0.0367 (18)	0.0147 (17)	0.0124 (16)	0.0043 (16)
C2	0.049 (2)	0.075 (2)	0.060 (2)	0.0018 (17)	0.0217 (18)	0.0043 (18)
C3	0.0388 (19)	0.0572 (19)	0.055 (2)	−0.0025 (15)	0.0105 (16)	−0.0061 (16)
C4	0.0461 (18)	0.0433 (17)	0.0394 (18)	0.0002 (14)	0.0137 (15)	0.0031 (13)
C5	0.050 (2)	0.0525 (18)	0.0387 (18)	0.0098 (15)	0.0086 (15)	−0.0024 (14)
C6	0.0353 (17)	0.061 (2)	0.0430 (19)	0.0040 (15)	0.0025 (15)	−0.0085 (15)
C7	0.054 (2)	0.076 (2)	0.050 (2)	0.0153 (18)	0.0106 (17)	−0.0104 (18)
C8	0.069 (3)	0.069 (2)	0.060 (2)	0.019 (2)	0.002 (2)	−0.005 (2)
C9	0.065 (3)	0.083 (3)	0.055 (2)	0.006 (2)	−0.003 (2)	0.014 (2)
C10	0.056 (2)	0.108 (3)	0.046 (2)	0.019 (2)	0.0111 (18)	0.009 (2)
C11	0.056 (2)	0.076 (2)	0.047 (2)	0.0232 (18)	0.0069 (17)	−0.0036 (18)
C12	0.0487 (19)	0.0378 (15)	0.049 (2)	−0.0010 (14)	0.0154 (17)	−0.0046 (14)
C13	0.069 (3)	0.072 (2)	0.047 (2)	−0.0169 (19)	0.0184 (19)	0.0010 (18)
C14	0.099 (3)	0.080 (3)	0.053 (2)	−0.034 (2)	0.037 (3)	−0.011 (2)
C15	0.069 (3)	0.065 (2)	0.091 (3)	−0.024 (2)	0.044 (3)	−0.027 (2)
C16	0.051 (2)	0.0567 (19)	0.088 (3)	−0.0036 (17)	0.018 (2)	−0.013 (2)
C17	0.049 (2)	0.0485 (18)	0.061 (2)	0.0009 (15)	0.0143 (19)	0.0016 (16)
C18	0.051 (2)	0.0435 (18)	0.053 (2)	−0.0006 (15)	0.0169 (17)	0.0006 (15)
C19	0.061 (2)	0.0439 (17)	0.068 (2)	0.0047 (15)	0.0152 (19)	−0.0038 (16)
C20	0.075 (3)	0.063 (2)	0.066 (2)	0.0087 (19)	0.013 (2)	−0.0142 (19)
C21	0.0509 (19)	0.0379 (15)	0.0357 (17)	0.0038 (14)	0.0117 (14)	0.0004 (13)
C22	0.055 (2)	0.0528 (19)	0.0436 (19)	0.0015 (16)	0.0183 (16)	−0.0069 (15)
C23	0.0430 (19)	0.058 (2)	0.055 (2)	0.0062 (16)	0.0172 (17)	0.0040 (17)
C24	0.049 (2)	0.0507 (18)	0.058 (2)	−0.0066 (15)	0.0133 (17)	−0.0029 (16)
C25	0.0441 (19)	0.0495 (18)	0.0411 (18)	−0.0006 (14)	0.0105 (15)	−0.0066 (15)
C26	0.049 (2)	0.0549 (18)	0.0374 (18)	0.0057 (15)	0.0101 (15)	−0.0041 (14)
C27	0.056 (2)	0.074 (2)	0.057 (2)	0.0151 (18)	0.0185 (18)	0.0047 (19)
C28	0.090 (3)	0.081 (3)	0.080 (3)	0.041 (2)	0.025 (2)	0.004 (2)
C29	0.125 (4)	0.069 (3)	0.080 (3)	0.035 (3)	0.023 (3)	0.020 (2)
C30	0.103 (3)	0.088 (3)	0.064 (3)	0.015 (3)	0.033 (2)	0.022 (2)
C31	0.070 (2)	0.072 (2)	0.056 (2)	0.0188 (19)	0.0251 (19)	0.0126 (19)
C32	0.054 (2)	0.0362 (16)	0.0416 (18)	0.0032 (14)	0.0196 (16)	−0.0060 (13)
C33	0.058 (2)	0.0447 (19)	0.055 (2)	0.0006 (16)	0.0115 (18)	−0.0064 (15)
C34	0.059 (2)	0.057 (2)	0.079 (3)	−0.0010 (18)	0.009 (2)	−0.021 (2)
C35	0.071 (3)	0.050 (2)	0.108 (3)	−0.015 (2)	0.034 (3)	−0.027 (2)
C36	0.093 (3)	0.042 (2)	0.097 (3)	−0.002 (2)	0.034 (3)	0.009 (2)
C37	0.069 (2)	0.0425 (18)	0.069 (2)	0.0015 (17)	0.0165 (19)	0.0029 (17)
C38	0.047 (2)	0.0411 (16)	0.0456 (19)	0.0016 (14)	0.0133 (16)	−0.0030 (15)
C39	0.055 (2)	0.0508 (19)	0.0492 (19)	0.0109 (15)	0.0166 (17)	−0.0045 (15)
C40	0.077 (3)	0.106 (3)	0.059 (2)	−0.009 (2)	0.029 (2)	−0.026 (2)

Geometric parameters (Å, º) top

Cl1—C19	1.771 (3)	C18—C19	1.522 (4)
Cl2—C39	1.769 (3)	C19—H19A	0.97
O1—C1	1.208 (3)	C19—H19B	0.97
O2—C18	1.221 (4)	C20—H20A	0.96
O3—C23	1.198 (3)	C20—H20B	0.96
O4—C38	1.224 (3)	C20—H20C	0.96
N1—C18	1.360 (4)	C21—C32	1.518 (4)
N1—C3	1.480 (4)	C21—C22	1.543 (4)
N1—C4	1.489 (4)	C21—H21	0.98
N2—C38	1.368 (3)	C22—C23	1.510 (4)
N2—C25	1.475 (4)	C22—C40	1.521 (4)
N2—C21	1.489 (3)	C22—H22	0.98
C1—C2	1.491 (5)	C23—C24	1.496 (4)
C1—C5	1.520 (4)	C24—C25	1.534 (4)
C2—C3	1.520 (4)	C24—H24A	0.97
C2—H2A	0.97	C24—H24B	0.97
C2—H2B	0.97	C25—C26	1.511 (4)
C3—C6	1.513 (4)	C25—H25	0.98
C3—H3	0.98	C26—C27	1.376 (4)
C4—C12	1.526 (4)	C26—C31	1.387 (4)
C4—C5	1.546 (4)	C27—C28	1.379 (5)
C4—H4	0.98	C27—H27	0.93
C5—C20	1.517 (4)	C28—C29	1.373 (6)
C5—H5	0.98	C28—H28	0.93
C6—C11	1.375 (4)	C29—C30	1.368 (5)
C6—C7	1.384 (4)	C29—H29	0.93
C7—C8	1.375 (5)	C30—C31	1.373 (5)
C7—H7	0.93	C30—H30	0.93
C8—C9	1.365 (5)	C31—H31	0.93
C8—H8	0.93	C32—C37	1.385 (4)
C9—C10	1.371 (5)	C32—C33	1.390 (4)
C9—H9	0.93	C33—C34	1.373 (4)
C10—C11	1.372 (5)	C33—H33	0.93
C10—H10	0.93	C34—C35	1.360 (5)
C11—H11	0.93	C34—H34	0.93
C12—C13	1.377 (4)	C35—C36	1.370 (5)
C12—C17	1.386 (4)	C35—H35	0.93
C13—C14	1.394 (5)	C36—C37	1.386 (5)
C13—H13	0.93	C36—H36	0.93
C14—C15	1.369 (5)	C37—H37	0.93
C14—H14	0.93	C38—C39	1.515 (4)
C15—C16	1.354 (5)	C39—H39A	0.97
C15—H15	0.93	C39—H39B	0.97
C16—C17	1.366 (5)	C40—H40A	0.96
C16—H16	0.93	C40—H40B	0.96
C17—H17	0.93	C40—H40C	0.96

C18—N1—C3	117.4 (3)	C5—C20—H20C	109.5
C18—N1—C4	122.9 (2)	H20A—C20—H20C	109.5
C3—N1—C4	118.7 (2)	H20B—C20—H20C	109.5
C38—N2—C25	117.2 (2)	N2—C21—C32	113.1 (2)
C38—N2—C21	121.6 (2)	N2—C21—C22	111.3 (2)
C25—N2—C21	119.9 (2)	C32—C21—C22	109.9 (2)
O1—C1—C2	122.1 (3)	N2—C21—H21	107.4
O1—C1—C5	122.0 (3)	C32—C21—H21	107.4
C2—C1—C5	116.0 (3)	C22—C21—H21	107.4
C1—C2—C3	113.0 (3)	C23—C22—C40	111.8 (3)
C1—C2—H2A	109.0	C23—C22—C21	111.2 (2)
C3—C2—H2A	109.0	C40—C22—C21	111.4 (3)
C1—C2—H2B	109.0	C23—C22—H22	107.4
C3—C2—H2B	109.0	C40—C22—H22	107.4
H2A—C2—H2B	107.8	C21—C22—H22	107.4
N1—C3—C6	113.0 (3)	O3—C23—C24	121.7 (3)
N1—C3—C2	107.3 (3)	O3—C23—C22	122.3 (3)
C6—C3—C2	116.3 (3)	C24—C23—C22	116.0 (3)
N1—C3—H3	106.6	C23—C24—C25	114.3 (3)
C6—C3—H3	106.6	C23—C24—H24A	108.7
C2—C3—H3	106.6	C25—C24—H24A	108.7
N1—C4—C12	112.0 (2)	C23—C24—H24B	108.7
N1—C4—C5	111.4 (2)	C25—C24—H24B	108.7
C12—C4—C5	110.3 (2)	H24A—C24—H24B	107.6
N1—C4—H4	107.6	N2—C25—C26	112.6 (2)
C12—C4—H4	107.6	N2—C25—C24	107.9 (2)
C5—C4—H4	107.6	C26—C25—C24	117.7 (3)
C20—C5—C1	112.7 (3)	N2—C25—H25	105.9
C20—C5—C4	112.1 (3)	C26—C25—H25	105.9
C1—C5—C4	110.3 (2)	C24—C25—H25	105.9
C20—C5—H5	107.1	C27—C26—C31	117.4 (3)
C1—C5—H5	107.1	C27—C26—C25	124.0 (3)
C4—C5—H5	107.1	C31—C26—C25	118.5 (3)
C11—C6—C7	117.0 (3)	C26—C27—C28	121.1 (3)
C11—C6—C3	118.8 (3)	C26—C27—H27	119.5
C7—C6—C3	124.2 (3)	C28—C27—H27	119.5
C8—C7—C6	121.5 (3)	C29—C28—C27	120.5 (4)
C8—C7—H7	119.2	C29—C28—H28	119.7
C6—C7—H7	119.2	C27—C28—H28	119.7
C9—C8—C7	119.9 (3)	C30—C29—C28	119.3 (4)
C9—C8—H8	120.0	C30—C29—H29	120.3
C7—C8—H8	120.0	C28—C29—H29	120.3
C8—C9—C10	119.9 (4)	C29—C30—C31	119.9 (4)
C8—C9—H9	120.0	C29—C30—H30	120.0
C10—C9—H9	120.0	C31—C30—H30	120.0
C9—C10—C11	119.5 (3)	C30—C31—C26	121.8 (3)
C9—C10—H10	120.2	C30—C31—H31	119.1
C11—C10—H10	120.2	C26—C31—H31	119.1
C10—C11—C6	122.1 (3)	C37—C32—C33	117.3 (3)
C10—C11—H11	118.9	C37—C32—C21	122.4 (3)
C6—C11—H11	118.9	C33—C32—C21	120.2 (3)
C13—C12—C17	118.3 (3)	C34—C33—C32	121.6 (3)
C13—C12—C4	121.4 (3)	C34—C33—H33	119.2
C17—C12—C4	120.3 (3)	C32—C33—H33	119.2
C12—C13—C14	119.9 (4)	C35—C34—C33	120.4 (4)
C12—C13—H13	120.0	C35—C34—H34	119.8
C14—C13—H13	120.0	C33—C34—H34	119.8
C15—C14—C13	120.1 (3)	C34—C35—C36	119.5 (3)
C15—C14—H14	119.9	C34—C35—H35	120.3
C13—C14—H14	119.9	C36—C35—H35	120.3
C16—C15—C14	120.0 (4)	C35—C36—C37	120.6 (4)
C16—C15—H15	120.0	C35—C36—H36	119.7
C14—C15—H15	120.0	C37—C36—H36	119.7
C15—C16—C17	120.4 (4)	C32—C37—C36	120.6 (4)
C15—C16—H16	119.8	C32—C37—H37	119.7
C17—C16—H16	119.8	C36—C37—H37	119.7
C16—C17—C12	121.2 (3)	O4—C38—N2	122.5 (3)
C16—C17—H17	119.4	O4—C38—C39	121.7 (3)
C12—C17—H17	119.4	N2—C38—C39	115.8 (3)
O2—C18—N1	123.6 (3)	C38—C39—Cl2	111.4 (2)
O2—C18—C19	121.4 (3)	C38—C39—H39A	109.3
N1—C18—C19	115.1 (3)	Cl2—C39—H39A	109.3
C18—C19—Cl1	112.2 (2)	C38—C39—H39B	109.3
C18—C19—H19A	109.2	Cl2—C39—H39B	109.3
Cl1—C19—H19A	109.2	H39A—C39—H39B	108.0
C18—C19—H19B	109.2	C22—C40—H40A	109.5
Cl1—C19—H19B	109.2	C22—C40—H40B	109.5
H19A—C19—H19B	107.9	H40A—C40—H40B	109.5
C5—C20—H20A	109.5	C22—C40—H40C	109.5
C5—C20—H20B	109.5	H40A—C40—H40C	109.5
H20A—C20—H20B	109.5	H40B—C40—H40C	109.5

O1—C1—C2—C3	−166.7 (3)	C38—N2—C21—C32	73.0 (3)
C5—C1—C2—C3	13.7 (4)	C25—N2—C21—C32	−120.2 (3)
C18—N1—C3—C6	109.4 (3)	C38—N2—C21—C22	−162.7 (2)
C4—N1—C3—C6	−81.7 (3)	C25—N2—C21—C22	4.1 (3)
C18—N1—C3—C2	−121.1 (3)	N2—C21—C22—C23	45.2 (3)
C4—N1—C3—C2	47.8 (3)	C32—C21—C22—C23	171.3 (3)
C1—C2—C3—N1	−57.4 (3)	N2—C21—C22—C40	170.7 (3)
C1—C2—C3—C6	70.2 (4)	C32—C21—C22—C40	−63.2 (3)
C18—N1—C4—C12	−62.3 (3)	C40—C22—C23—O3	7.8 (5)
C3—N1—C4—C12	129.4 (3)	C21—C22—C23—O3	133.1 (3)
C18—N1—C4—C5	173.6 (3)	C40—C22—C23—C24	−172.2 (3)
C3—N1—C4—C5	5.3 (3)	C21—C22—C23—C24	−46.9 (4)
O1—C1—C5—C20	−13.2 (4)	O3—C23—C24—C25	178.8 (3)
C2—C1—C5—C20	166.4 (3)	C22—C23—C24—C25	−1.2 (4)
O1—C1—C5—C4	−139.4 (3)	C38—N2—C25—C26	−111.9 (3)
C2—C1—C5—C4	40.2 (4)	C21—N2—C25—C26	80.7 (3)
N1—C4—C5—C20	−176.3 (3)	C38—N2—C25—C24	116.5 (3)
C12—C4—C5—C20	58.6 (3)	C21—N2—C25—C24	−50.8 (3)
N1—C4—C5—C1	−49.8 (3)	C23—C24—C25—N2	48.3 (3)
C12—C4—C5—C1	−174.9 (2)	C23—C24—C25—C26	−80.4 (4)
N1—C3—C6—C11	−51.3 (4)	N2—C25—C26—C27	−124.2 (3)
C2—C3—C6—C11	−176.0 (3)	C24—C25—C26—C27	2.3 (4)
N1—C3—C6—C7	129.2 (3)	N2—C25—C26—C31	59.0 (4)
C2—C3—C6—C7	4.5 (4)	C24—C25—C26—C31	−174.5 (3)
C11—C6—C7—C8	1.8 (5)	C31—C26—C27—C28	−2.2 (5)
C3—C6—C7—C8	−178.7 (3)	C25—C26—C27—C28	−179.0 (3)
C6—C7—C8—C9	0.2 (5)	C26—C27—C28—C29	0.5 (6)
C7—C8—C9—C10	−1.8 (5)	C27—C28—C29—C30	1.1 (7)
C8—C9—C10—C11	1.4 (6)	C28—C29—C30—C31	−1.0 (7)
C9—C10—C11—C6	0.7 (6)	C29—C30—C31—C26	−0.7 (6)
C7—C6—C11—C10	−2.2 (5)	C27—C26—C31—C30	2.3 (5)
C3—C6—C11—C10	178.3 (3)	C25—C26—C31—C30	179.3 (3)
N1—C4—C12—C13	−50.8 (4)	N2—C21—C32—C37	53.2 (4)
C5—C4—C12—C13	74.0 (3)	C22—C21—C32—C37	−71.8 (4)
N1—C4—C12—C17	129.3 (3)	N2—C21—C32—C33	−129.5 (3)
C5—C4—C12—C17	−105.9 (3)	C22—C21—C32—C33	105.5 (3)
C17—C12—C13—C14	−1.3 (5)	C37—C32—C33—C34	−0.3 (4)
C4—C12—C13—C14	178.8 (3)	C21—C32—C33—C34	−177.7 (3)
C12—C13—C14—C15	0.3 (5)	C32—C33—C34—C35	−0.2 (5)
C13—C14—C15—C16	0.3 (5)	C33—C34—C35—C36	0.3 (5)
C14—C15—C16—C17	0.1 (5)	C34—C35—C36—C37	0.1 (6)
C15—C16—C17—C12	−1.1 (5)	C33—C32—C37—C36	0.7 (5)
C13—C12—C17—C16	1.8 (4)	C21—C32—C37—C36	178.0 (3)
C4—C12—C17—C16	−178.3 (3)	C35—C36—C37—C32	−0.6 (6)
C3—N1—C18—O2	−14.2 (4)	C25—N2—C38—O4	12.3 (4)
C4—N1—C18—O2	177.4 (3)	C21—N2—C38—O4	179.5 (3)
C3—N1—C18—C19	164.4 (3)	C25—N2—C38—C39	−166.5 (2)
C4—N1—C18—C19	−4.0 (4)	C21—N2—C38—C39	0.6 (4)
O2—C18—C19—Cl1	4.6 (4)	O4—C38—C39—Cl2	4.0 (4)
N1—C18—C19—Cl1	−174.0 (2)	N2—C38—C39—Cl2	−177.1 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀ClNO₂
M_r	341.82
Crystal system, space group	Monoclinic, Cc
Temperature (K)	290
a, b, c (Å)	31.026 (6), 12.417 (2), 9.3209 (17)
β (°)	101.423 (4)
V (Å³)	3519.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.23 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	14797, 7013, 4933
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.094, 1.05
No. of reflections	7013
No. of parameters	435
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.14
Absolute structure	Flack (1983), 3002 Friedel pairs
Absolute structure parameter	0.04 (5)

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

The authors thank the Department of Science and Technology, India, for use of the diffraction facility set up under the IRHPA–DST programme at IISc. FNK thanks the DST for Fast Track Proposal funding. The authors also thank VIT University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kumar, N. A., Kim, J. S. & Jeong, Y. T. (2008). Acta Cryst. E64, o1631. Web of Science CSD CrossRef IUCr Journals 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
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar