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Acta Cryst. (2009). E65, o2985    [ doi:10.1107/S1600536809045358 ]

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

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

Abstract top

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 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 m−3
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 mm−1
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)
graphiteRint = 0.036
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −38→40
Tmin = 0.945, Tmax = 0.956k = −16→16
14797 measured reflectionsl = −11→12
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 Å−3
435 parametersΔρmin = −0.13 e Å−3
2 restraintsAbsolute structure: Flack (1983), 3002 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack 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 mm−1
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 reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.31 e Å−3
S = 1.05Δρmin = −0.13 e Å−3
7013 reflectionsAbsolute structure: Flack (1983), 3002 Friedel pairs
435 parametersFlack 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)
H290.21411.0192−0.09230.109*
C300.25681 (15)0.8972 (4)−0.0860 (4)0.0827 (12)
H300.27190.9256−0.15430.099*
C310.26915 (12)0.7997 (3)−0.0212 (4)0.0644 (10)
H310.29240.7624−0.04740.077*
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, °) 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—C3−166.7 (3)C38—N2—C21—C3273.0 (3)
C5—C1—C2—C313.7 (4)C25—N2—C21—C32−120.2 (3)
C18—N1—C3—C6109.4 (3)C38—N2—C21—C22−162.7 (2)
C4—N1—C3—C6−81.7 (3)C25—N2—C21—C224.1 (3)
C18—N1—C3—C2−121.1 (3)N2—C21—C22—C2345.2 (3)
C4—N1—C3—C247.8 (3)C32—C21—C22—C23171.3 (3)
C1—C2—C3—N1−57.4 (3)N2—C21—C22—C40170.7 (3)
C1—C2—C3—C670.2 (4)C32—C21—C22—C40−63.2 (3)
C18—N1—C4—C12−62.3 (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—C24−172.2 (3)
C3—N1—C4—C55.3 (3)C21—C22—C23—C24−46.9 (4)
O1—C1—C5—C20−13.2 (4)O3—C23—C24—C25178.8 (3)
C2—C1—C5—C20166.4 (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—C440.2 (4)C21—N2—C25—C2680.7 (3)
N1—C4—C5—C20−176.3 (3)C38—N2—C25—C24116.5 (3)
C12—C4—C5—C2058.6 (3)C21—N2—C25—C24−50.8 (3)
N1—C4—C5—C1−49.8 (3)C23—C24—C25—N248.3 (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—C272.3 (4)
N1—C3—C6—C7129.2 (3)N2—C25—C26—C3159.0 (4)
C2—C3—C6—C74.5 (4)C24—C25—C26—C31−174.5 (3)
C11—C6—C7—C81.8 (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—C90.2 (5)C26—C27—C28—C290.5 (6)
C7—C8—C9—C10−1.8 (5)C27—C28—C29—C301.1 (7)
C8—C9—C10—C111.4 (6)C28—C29—C30—C31−1.0 (7)
C9—C10—C11—C60.7 (6)C29—C30—C31—C26−0.7 (6)
C7—C6—C11—C10−2.2 (5)C27—C26—C31—C302.3 (5)
C3—C6—C11—C10178.3 (3)C25—C26—C31—C30179.3 (3)
N1—C4—C12—C13−50.8 (4)N2—C21—C32—C3753.2 (4)
C5—C4—C12—C1374.0 (3)C22—C21—C32—C37−71.8 (4)
N1—C4—C12—C17129.3 (3)N2—C21—C32—C33−129.5 (3)
C5—C4—C12—C17−105.9 (3)C22—C21—C32—C33105.5 (3)
C17—C12—C13—C14−1.3 (5)C37—C32—C33—C34−0.3 (4)
C4—C12—C13—C14178.8 (3)C21—C32—C33—C34−177.7 (3)
C12—C13—C14—C150.3 (5)C32—C33—C34—C35−0.2 (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—C12−1.1 (5)C33—C32—C37—C360.7 (5)
C13—C12—C17—C161.8 (4)C21—C32—C37—C36178.0 (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—O412.3 (4)
C4—N1—C18—O2177.4 (3)C21—N2—C38—O4179.5 (3)
C3—N1—C18—C19164.4 (3)C25—N2—C38—C39−166.5 (2)
C4—N1—C18—C19−4.0 (4)C21—N2—C38—C390.6 (4)
O2—C18—C19—Cl14.6 (4)O4—C38—C39—Cl24.0 (4)
N1—C18—C19—Cl1−174.0 (2)N2—C38—C39—Cl2−177.1 (2)
Acknowledgements top

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
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

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

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.