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

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ISSN: 2056-9890

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

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[Parthiban, P., Ramkumar, V., Kumar, N. A., Kim, J. S. & Jeong, Y. T. (2008). Acta Cryst. E64, o1631.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20ClNO2

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.945, Tmax = 0.956

  • 14797 measured reflections

  • 7013 independent reflections

  • 4933 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.14 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3002 Friedel pairs

  • Flack parameter: 0.04 (5)

Data collection: SMART (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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.

Refinement top

C-bound H-atoms were placed in calculated positions (C-H = 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C).

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
[Figure 1] 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
C20H20ClNO2F(000) = 1440
Mr = 341.82Dx = 1.290 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1325 reflections
a = 31.026 (6) Åθ = 3.0–20.7°
b = 12.417 (2) ŵ = 0.23 mm1
c = 9.3209 (17) ÅT = 290 K
β = 101.423 (4)°Block, colourless
V = 3519.8 (11) Å30.25 × 0.23 × 0.20 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
7013 independent reflections
Radiation source: fine-focus sealed tube4933 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3840
Tmin = 0.945, Tmax = 0.956k = 1616
14797 measured reflectionsl = 1112
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0334P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
7013 reflectionsΔρmax = 0.31 e Å3
435 parametersΔρmin = 0.14 e Å3
2 restraintsAbsolute structure: Flack (1983), 3002 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (5)
Crystal data top
C20H20ClNO2V = 3519.8 (11) Å3
Mr = 341.82Z = 8
Monoclinic, CcMo Kα radiation
a = 31.026 (6) ŵ = 0.23 mm1
b = 12.417 (2) ÅT = 290 K
c = 9.3209 (17) Å0.25 × 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)
Tmin = 0.945, Tmax = 0.956Rint = 0.036
14797 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.31 e Å3
S = 1.05Δρmin = 0.14 e Å3
7013 reflectionsAbsolute structure: Flack (1983), 3002 Friedel pairs
435 parametersAbsolute structure parameter: 0.04 (5)
2 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.50000 (3)0.64105 (6)0.50836 (9)0.0634 (2)
Cl20.41803 (3)0.49823 (7)0.15694 (9)0.0608 (2)
O10.63439 (8)0.1780 (2)0.3091 (3)0.0758 (7)
O20.57673 (8)0.53213 (18)0.6705 (3)0.0685 (7)
O30.22780 (8)0.6049 (2)0.4959 (3)0.0728 (7)
O40.32828 (7)0.55176 (18)0.0346 (2)0.0622 (6)
N10.57108 (8)0.3715 (2)0.5510 (2)0.0430 (6)
N20.30973 (8)0.64746 (17)0.2214 (2)0.0405 (6)
C10.61735 (10)0.2246 (3)0.3972 (3)0.0510 (8)
C20.63947 (11)0.3156 (3)0.4873 (4)0.0598 (9)
H2A0.63950.37820.42510.072*
H2B0.66980.29610.52580.072*
C30.61746 (10)0.3449 (3)0.6139 (3)0.0501 (8)
H30.63130.41180.65600.060*
C40.54533 (10)0.2968 (2)0.4414 (3)0.0422 (7)
H40.53910.33440.34710.051*
C50.57193 (10)0.1944 (2)0.4222 (3)0.0470 (8)
H50.57610.15450.51460.056*
C60.62226 (10)0.2644 (3)0.7379 (3)0.0472 (8)
C70.64743 (11)0.1717 (3)0.7463 (4)0.0602 (9)
H70.66310.15740.67300.072*
C80.64984 (12)0.1004 (3)0.8605 (4)0.0675 (10)
H80.66700.03880.86400.081*
C90.62698 (13)0.1204 (3)0.9686 (4)0.0695 (10)
H90.62790.07131.04460.083*
C100.60264 (12)0.2128 (3)0.9652 (4)0.0698 (11)
H100.58750.22741.03970.084*
C110.60076 (11)0.2835 (3)0.8510 (3)0.0598 (9)
H110.58440.34640.85010.072*
C120.50134 (10)0.2664 (2)0.4800 (3)0.0443 (7)
C130.49875 (13)0.2290 (3)0.6171 (4)0.0621 (10)
H130.52420.22040.68800.074*
C140.45792 (15)0.2039 (3)0.6495 (4)0.0744 (12)
H140.45620.17900.74230.089*
C150.42043 (14)0.2160 (3)0.5452 (5)0.0713 (11)
H150.39320.19960.56720.086*
C160.42293 (12)0.2519 (3)0.4098 (5)0.0649 (9)
H160.39740.26010.33920.078*
C170.46276 (10)0.2760 (2)0.3765 (4)0.0524 (8)
H170.46400.29930.28260.063*
C180.55669 (10)0.4715 (2)0.5775 (4)0.0480 (8)
C190.51356 (11)0.5052 (2)0.4795 (4)0.0570 (9)
H19A0.49020.45890.49850.068*
H19B0.51580.49580.37800.068*
C200.54732 (12)0.1207 (3)0.3038 (4)0.0682 (10)
H20A0.56660.06470.28400.102*
H20B0.53710.16160.21630.102*
H20C0.52260.08930.33630.102*
C210.32251 (10)0.6907 (2)0.3728 (3)0.0411 (7)
H210.33750.63270.43470.049*
C220.28172 (11)0.7229 (3)0.4345 (3)0.0492 (8)
H220.26960.78840.38330.059*
C230.24657 (10)0.6372 (3)0.4037 (4)0.0510 (8)
C240.23644 (11)0.5946 (3)0.2506 (3)0.0520 (8)
H24A0.20540.60530.21090.062*
H24B0.24200.51770.25340.062*
C250.26308 (10)0.6470 (2)0.1472 (3)0.0446 (7)
H250.26110.59770.06410.054*
C260.24783 (10)0.7553 (2)0.0823 (3)0.0470 (8)
C270.21257 (12)0.8110 (3)0.1142 (4)0.0613 (9)
H270.19700.78220.18060.074*
C280.20001 (14)0.9089 (3)0.0493 (4)0.0825 (12)
H280.17620.94550.07300.099*
C290.22233 (16)0.9526 (3)0.0500 (5)0.0910 (14)
H290.21411.01920.09230.109*
C300.25681 (15)0.8972 (4)0.0860 (4)0.0827 (12)
H300.27190.92560.15430.099*
C310.26915 (12)0.7997 (3)0.0212 (4)0.0644 (10)
H310.29240.76240.04740.077*
C320.35415 (10)0.7850 (2)0.3844 (3)0.0427 (7)
C330.39264 (11)0.7851 (3)0.4903 (3)0.0525 (8)
H330.39920.72560.55130.063*
C340.42113 (12)0.8708 (3)0.5068 (4)0.0656 (10)
H340.44660.86880.57870.079*
C350.41234 (14)0.9586 (3)0.4187 (5)0.0741 (12)
H350.43181.01640.42980.089*
C360.37464 (15)0.9612 (3)0.3134 (5)0.0749 (11)
H360.36861.02110.25280.090*
C370.34551 (13)0.8754 (2)0.2963 (4)0.0597 (9)
H370.31990.87850.22490.072*
C380.33837 (10)0.5885 (2)0.1586 (3)0.0439 (7)
C390.38335 (10)0.5695 (3)0.2533 (3)0.0506 (8)
H39A0.38020.52880.33950.061*
H39B0.39670.63820.28560.061*
C400.29396 (13)0.7496 (4)0.5967 (4)0.0788 (12)
H40A0.31090.69160.64770.118*
H40B0.26770.75940.63490.118*
H40C0.31100.81460.60980.118*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0701 (6)0.0429 (4)0.0813 (6)0.0046 (4)0.0246 (5)0.0002 (4)
Cl20.0606 (5)0.0579 (5)0.0667 (5)0.0203 (4)0.0193 (4)0.0063 (4)
O10.0668 (16)0.109 (2)0.0558 (15)0.0238 (15)0.0222 (13)0.0105 (14)
O20.0717 (17)0.0582 (14)0.0703 (16)0.0018 (12)0.0007 (14)0.0201 (13)
O30.0627 (17)0.100 (2)0.0621 (16)0.0086 (14)0.0277 (14)0.0125 (14)
O40.0593 (15)0.0758 (15)0.0515 (15)0.0092 (12)0.0109 (12)0.0225 (13)
N10.0408 (15)0.0484 (15)0.0405 (15)0.0006 (12)0.0094 (12)0.0013 (11)
N20.0452 (15)0.0410 (13)0.0375 (15)0.0034 (12)0.0134 (13)0.0056 (11)
C10.050 (2)0.068 (2)0.0367 (18)0.0147 (17)0.0124 (16)0.0043 (16)
C20.049 (2)0.075 (2)0.060 (2)0.0018 (17)0.0217 (18)0.0043 (18)
C30.0388 (19)0.0572 (19)0.055 (2)0.0025 (15)0.0105 (16)0.0061 (16)
C40.0461 (18)0.0433 (17)0.0394 (18)0.0002 (14)0.0137 (15)0.0031 (13)
C50.050 (2)0.0525 (18)0.0387 (18)0.0098 (15)0.0086 (15)0.0024 (14)
C60.0353 (17)0.061 (2)0.0430 (19)0.0040 (15)0.0025 (15)0.0085 (15)
C70.054 (2)0.076 (2)0.050 (2)0.0153 (18)0.0106 (17)0.0104 (18)
C80.069 (3)0.069 (2)0.060 (2)0.019 (2)0.002 (2)0.005 (2)
C90.065 (3)0.083 (3)0.055 (2)0.006 (2)0.003 (2)0.014 (2)
C100.056 (2)0.108 (3)0.046 (2)0.019 (2)0.0111 (18)0.009 (2)
C110.056 (2)0.076 (2)0.047 (2)0.0232 (18)0.0069 (17)0.0036 (18)
C120.0487 (19)0.0378 (15)0.049 (2)0.0010 (14)0.0154 (17)0.0046 (14)
C130.069 (3)0.072 (2)0.047 (2)0.0169 (19)0.0184 (19)0.0010 (18)
C140.099 (3)0.080 (3)0.053 (2)0.034 (2)0.037 (3)0.011 (2)
C150.069 (3)0.065 (2)0.091 (3)0.024 (2)0.044 (3)0.027 (2)
C160.051 (2)0.0567 (19)0.088 (3)0.0036 (17)0.018 (2)0.013 (2)
C170.049 (2)0.0485 (18)0.061 (2)0.0009 (15)0.0143 (19)0.0016 (16)
C180.051 (2)0.0435 (18)0.053 (2)0.0006 (15)0.0169 (17)0.0006 (15)
C190.061 (2)0.0439 (17)0.068 (2)0.0047 (15)0.0152 (19)0.0038 (16)
C200.075 (3)0.063 (2)0.066 (2)0.0087 (19)0.013 (2)0.0142 (19)
C210.0509 (19)0.0379 (15)0.0357 (17)0.0038 (14)0.0117 (14)0.0004 (13)
C220.055 (2)0.0528 (19)0.0436 (19)0.0015 (16)0.0183 (16)0.0069 (15)
C230.0430 (19)0.058 (2)0.055 (2)0.0062 (16)0.0172 (17)0.0040 (17)
C240.049 (2)0.0507 (18)0.058 (2)0.0066 (15)0.0133 (17)0.0029 (16)
C250.0441 (19)0.0495 (18)0.0411 (18)0.0006 (14)0.0105 (15)0.0066 (15)
C260.049 (2)0.0549 (18)0.0374 (18)0.0057 (15)0.0101 (15)0.0041 (14)
C270.056 (2)0.074 (2)0.057 (2)0.0151 (18)0.0185 (18)0.0047 (19)
C280.090 (3)0.081 (3)0.080 (3)0.041 (2)0.025 (2)0.004 (2)
C290.125 (4)0.069 (3)0.080 (3)0.035 (3)0.023 (3)0.020 (2)
C300.103 (3)0.088 (3)0.064 (3)0.015 (3)0.033 (2)0.022 (2)
C310.070 (2)0.072 (2)0.056 (2)0.0188 (19)0.0251 (19)0.0126 (19)
C320.054 (2)0.0362 (16)0.0416 (18)0.0032 (14)0.0196 (16)0.0060 (13)
C330.058 (2)0.0447 (19)0.055 (2)0.0006 (16)0.0115 (18)0.0064 (15)
C340.059 (2)0.057 (2)0.079 (3)0.0010 (18)0.009 (2)0.021 (2)
C350.071 (3)0.050 (2)0.108 (3)0.015 (2)0.034 (3)0.027 (2)
C360.093 (3)0.042 (2)0.097 (3)0.002 (2)0.034 (3)0.009 (2)
C370.069 (2)0.0425 (18)0.069 (2)0.0015 (17)0.0165 (19)0.0029 (17)
C380.047 (2)0.0411 (16)0.0456 (19)0.0016 (14)0.0133 (16)0.0030 (15)
C390.055 (2)0.0508 (19)0.0492 (19)0.0109 (15)0.0166 (17)0.0045 (15)
C400.077 (3)0.106 (3)0.059 (2)0.009 (2)0.029 (2)0.026 (2)
Geometric parameters (Å, º) top
Cl1—C191.771 (3)C18—C191.522 (4)
Cl2—C391.769 (3)C19—H19A0.97
O1—C11.208 (3)C19—H19B0.97
O2—C181.221 (4)C20—H20A0.96
O3—C231.198 (3)C20—H20B0.96
O4—C381.224 (3)C20—H20C0.96
N1—C181.360 (4)C21—C321.518 (4)
N1—C31.480 (4)C21—C221.543 (4)
N1—C41.489 (4)C21—H210.98
N2—C381.368 (3)C22—C231.510 (4)
N2—C251.475 (4)C22—C401.521 (4)
N2—C211.489 (3)C22—H220.98
C1—C21.491 (5)C23—C241.496 (4)
C1—C51.520 (4)C24—C251.534 (4)
C2—C31.520 (4)C24—H24A0.97
C2—H2A0.97C24—H24B0.97
C2—H2B0.97C25—C261.511 (4)
C3—C61.513 (4)C25—H250.98
C3—H30.98C26—C271.376 (4)
C4—C121.526 (4)C26—C311.387 (4)
C4—C51.546 (4)C27—C281.379 (5)
C4—H40.98C27—H270.93
C5—C201.517 (4)C28—C291.373 (6)
C5—H50.98C28—H280.93
C6—C111.375 (4)C29—C301.368 (5)
C6—C71.384 (4)C29—H290.93
C7—C81.375 (5)C30—C311.373 (5)
C7—H70.93C30—H300.93
C8—C91.365 (5)C31—H310.93
C8—H80.93C32—C371.385 (4)
C9—C101.371 (5)C32—C331.390 (4)
C9—H90.93C33—C341.373 (4)
C10—C111.372 (5)C33—H330.93
C10—H100.93C34—C351.360 (5)
C11—H110.93C34—H340.93
C12—C131.377 (4)C35—C361.370 (5)
C12—C171.386 (4)C35—H350.93
C13—C141.394 (5)C36—C371.386 (5)
C13—H130.93C36—H360.93
C14—C151.369 (5)C37—H370.93
C14—H140.93C38—C391.515 (4)
C15—C161.354 (5)C39—H39A0.97
C15—H150.93C39—H39B0.97
C16—C171.366 (5)C40—H40A0.96
C16—H160.93C40—H40B0.96
C17—H170.93C40—H40C0.96
C18—N1—C3117.4 (3)C5—C20—H20C109.5
C18—N1—C4122.9 (2)H20A—C20—H20C109.5
C3—N1—C4118.7 (2)H20B—C20—H20C109.5
C38—N2—C25117.2 (2)N2—C21—C32113.1 (2)
C38—N2—C21121.6 (2)N2—C21—C22111.3 (2)
C25—N2—C21119.9 (2)C32—C21—C22109.9 (2)
O1—C1—C2122.1 (3)N2—C21—H21107.4
O1—C1—C5122.0 (3)C32—C21—H21107.4
C2—C1—C5116.0 (3)C22—C21—H21107.4
C1—C2—C3113.0 (3)C23—C22—C40111.8 (3)
C1—C2—H2A109.0C23—C22—C21111.2 (2)
C3—C2—H2A109.0C40—C22—C21111.4 (3)
C1—C2—H2B109.0C23—C22—H22107.4
C3—C2—H2B109.0C40—C22—H22107.4
H2A—C2—H2B107.8C21—C22—H22107.4
N1—C3—C6113.0 (3)O3—C23—C24121.7 (3)
N1—C3—C2107.3 (3)O3—C23—C22122.3 (3)
C6—C3—C2116.3 (3)C24—C23—C22116.0 (3)
N1—C3—H3106.6C23—C24—C25114.3 (3)
C6—C3—H3106.6C23—C24—H24A108.7
C2—C3—H3106.6C25—C24—H24A108.7
N1—C4—C12112.0 (2)C23—C24—H24B108.7
N1—C4—C5111.4 (2)C25—C24—H24B108.7
C12—C4—C5110.3 (2)H24A—C24—H24B107.6
N1—C4—H4107.6N2—C25—C26112.6 (2)
C12—C4—H4107.6N2—C25—C24107.9 (2)
C5—C4—H4107.6C26—C25—C24117.7 (3)
C20—C5—C1112.7 (3)N2—C25—H25105.9
C20—C5—C4112.1 (3)C26—C25—H25105.9
C1—C5—C4110.3 (2)C24—C25—H25105.9
C20—C5—H5107.1C27—C26—C31117.4 (3)
C1—C5—H5107.1C27—C26—C25124.0 (3)
C4—C5—H5107.1C31—C26—C25118.5 (3)
C11—C6—C7117.0 (3)C26—C27—C28121.1 (3)
C11—C6—C3118.8 (3)C26—C27—H27119.5
C7—C6—C3124.2 (3)C28—C27—H27119.5
C8—C7—C6121.5 (3)C29—C28—C27120.5 (4)
C8—C7—H7119.2C29—C28—H28119.7
C6—C7—H7119.2C27—C28—H28119.7
C9—C8—C7119.9 (3)C30—C29—C28119.3 (4)
C9—C8—H8120.0C30—C29—H29120.3
C7—C8—H8120.0C28—C29—H29120.3
C8—C9—C10119.9 (4)C29—C30—C31119.9 (4)
C8—C9—H9120.0C29—C30—H30120.0
C10—C9—H9120.0C31—C30—H30120.0
C9—C10—C11119.5 (3)C30—C31—C26121.8 (3)
C9—C10—H10120.2C30—C31—H31119.1
C11—C10—H10120.2C26—C31—H31119.1
C10—C11—C6122.1 (3)C37—C32—C33117.3 (3)
C10—C11—H11118.9C37—C32—C21122.4 (3)
C6—C11—H11118.9C33—C32—C21120.2 (3)
C13—C12—C17118.3 (3)C34—C33—C32121.6 (3)
C13—C12—C4121.4 (3)C34—C33—H33119.2
C17—C12—C4120.3 (3)C32—C33—H33119.2
C12—C13—C14119.9 (4)C35—C34—C33120.4 (4)
C12—C13—H13120.0C35—C34—H34119.8
C14—C13—H13120.0C33—C34—H34119.8
C15—C14—C13120.1 (3)C34—C35—C36119.5 (3)
C15—C14—H14119.9C34—C35—H35120.3
C13—C14—H14119.9C36—C35—H35120.3
C16—C15—C14120.0 (4)C35—C36—C37120.6 (4)
C16—C15—H15120.0C35—C36—H36119.7
C14—C15—H15120.0C37—C36—H36119.7
C15—C16—C17120.4 (4)C32—C37—C36120.6 (4)
C15—C16—H16119.8C32—C37—H37119.7
C17—C16—H16119.8C36—C37—H37119.7
C16—C17—C12121.2 (3)O4—C38—N2122.5 (3)
C16—C17—H17119.4O4—C38—C39121.7 (3)
C12—C17—H17119.4N2—C38—C39115.8 (3)
O2—C18—N1123.6 (3)C38—C39—Cl2111.4 (2)
O2—C18—C19121.4 (3)C38—C39—H39A109.3
N1—C18—C19115.1 (3)Cl2—C39—H39A109.3
C18—C19—Cl1112.2 (2)C38—C39—H39B109.3
C18—C19—H19A109.2Cl2—C39—H39B109.3
Cl1—C19—H19A109.2H39A—C39—H39B108.0
C18—C19—H19B109.2C22—C40—H40A109.5
Cl1—C19—H19B109.2C22—C40—H40B109.5
H19A—C19—H19B107.9H40A—C40—H40B109.5
C5—C20—H20A109.5C22—C40—H40C109.5
C5—C20—H20B109.5H40A—C40—H40C109.5
H20A—C20—H20B109.5H40B—C40—H40C109.5
O1—C1—C2—C3166.7 (3)C38—N2—C21—C3273.0 (3)
C5—C1—C2—C313.7 (4)C25—N2—C21—C32120.2 (3)
C18—N1—C3—C6109.4 (3)C38—N2—C21—C22162.7 (2)
C4—N1—C3—C681.7 (3)C25—N2—C21—C224.1 (3)
C18—N1—C3—C2121.1 (3)N2—C21—C22—C2345.2 (3)
C4—N1—C3—C247.8 (3)C32—C21—C22—C23171.3 (3)
C1—C2—C3—N157.4 (3)N2—C21—C22—C40170.7 (3)
C1—C2—C3—C670.2 (4)C32—C21—C22—C4063.2 (3)
C18—N1—C4—C1262.3 (3)C40—C22—C23—O37.8 (5)
C3—N1—C4—C12129.4 (3)C21—C22—C23—O3133.1 (3)
C18—N1—C4—C5173.6 (3)C40—C22—C23—C24172.2 (3)
C3—N1—C4—C55.3 (3)C21—C22—C23—C2446.9 (4)
O1—C1—C5—C2013.2 (4)O3—C23—C24—C25178.8 (3)
C2—C1—C5—C20166.4 (3)C22—C23—C24—C251.2 (4)
O1—C1—C5—C4139.4 (3)C38—N2—C25—C26111.9 (3)
C2—C1—C5—C440.2 (4)C21—N2—C25—C2680.7 (3)
N1—C4—C5—C20176.3 (3)C38—N2—C25—C24116.5 (3)
C12—C4—C5—C2058.6 (3)C21—N2—C25—C2450.8 (3)
N1—C4—C5—C149.8 (3)C23—C24—C25—N248.3 (3)
C12—C4—C5—C1174.9 (2)C23—C24—C25—C2680.4 (4)
N1—C3—C6—C1151.3 (4)N2—C25—C26—C27124.2 (3)
C2—C3—C6—C11176.0 (3)C24—C25—C26—C272.3 (4)
N1—C3—C6—C7129.2 (3)N2—C25—C26—C3159.0 (4)
C2—C3—C6—C74.5 (4)C24—C25—C26—C31174.5 (3)
C11—C6—C7—C81.8 (5)C31—C26—C27—C282.2 (5)
C3—C6—C7—C8178.7 (3)C25—C26—C27—C28179.0 (3)
C6—C7—C8—C90.2 (5)C26—C27—C28—C290.5 (6)
C7—C8—C9—C101.8 (5)C27—C28—C29—C301.1 (7)
C8—C9—C10—C111.4 (6)C28—C29—C30—C311.0 (7)
C9—C10—C11—C60.7 (6)C29—C30—C31—C260.7 (6)
C7—C6—C11—C102.2 (5)C27—C26—C31—C302.3 (5)
C3—C6—C11—C10178.3 (3)C25—C26—C31—C30179.3 (3)
N1—C4—C12—C1350.8 (4)N2—C21—C32—C3753.2 (4)
C5—C4—C12—C1374.0 (3)C22—C21—C32—C3771.8 (4)
N1—C4—C12—C17129.3 (3)N2—C21—C32—C33129.5 (3)
C5—C4—C12—C17105.9 (3)C22—C21—C32—C33105.5 (3)
C17—C12—C13—C141.3 (5)C37—C32—C33—C340.3 (4)
C4—C12—C13—C14178.8 (3)C21—C32—C33—C34177.7 (3)
C12—C13—C14—C150.3 (5)C32—C33—C34—C350.2 (5)
C13—C14—C15—C160.3 (5)C33—C34—C35—C360.3 (5)
C14—C15—C16—C170.1 (5)C34—C35—C36—C370.1 (6)
C15—C16—C17—C121.1 (5)C33—C32—C37—C360.7 (5)
C13—C12—C17—C161.8 (4)C21—C32—C37—C36178.0 (3)
C4—C12—C17—C16178.3 (3)C35—C36—C37—C320.6 (6)
C3—N1—C18—O214.2 (4)C25—N2—C38—O412.3 (4)
C4—N1—C18—O2177.4 (3)C21—N2—C38—O4179.5 (3)
C3—N1—C18—C19164.4 (3)C25—N2—C38—C39166.5 (2)
C4—N1—C18—C194.0 (4)C21—N2—C38—C390.6 (4)
O2—C18—C19—Cl14.6 (4)O4—C38—C39—Cl24.0 (4)
N1—C18—C19—Cl1174.0 (2)N2—C38—C39—Cl2177.1 (2)

Experimental details

Crystal data
Chemical formulaC20H20ClNO2
Mr341.82
Crystal system, space groupMonoclinic, Cc
Temperature (K)290
a, b, c (Å)31.026 (6), 12.417 (2), 9.3209 (17)
β (°) 101.423 (4)
V3)3519.8 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.25 × 0.23 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.945, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
14797, 7013, 4933
Rint0.036
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.094, 1.05
No. of reflections7013
No. of parameters435
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.14
Absolute structureFlack (1983), 3002 Friedel pairs
Absolute structure parameter0.04 (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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationParthiban, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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