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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2985.
Published online 2009 November 4. doi:  10.1107/S1600536809045358
PMCID: PMC2971901

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

Abstract

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 [triangle]).

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Object name is e-65-o2985-scheme1.jpg

Experimental

Crystal data

  • C20H20ClNO2
  • M r = 341.82
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2985-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 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 [triangle]), 3002 Friedel pairs
  • Flack parameter: 0.04 (5)

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

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Experimental

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

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).

Figures

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

Crystal data

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

Bruker SMART CCD area-detector diffractometer7013 independent reflections
Radiation source: fine-focus sealed tube4933 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] 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

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) = 0.094w = 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 = −0.13 e Å3
2 restraintsAbsolute structure: Flack (1983), 3002 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (5)

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2956).

References

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