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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2883.
Published online 2009 October 28. doi:  10.1107/S1600536809043281
PMCID: PMC2971376

1-Chloro­acetyl-r-2,c-6-bis­(4-methoxy­phen­yl)-t-3-methyl­piperidin-4-one

Abstract

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C22H24ClNO4. The piperidine ring in both mol­ecules adopts a distorted boat conformation. The crystal packing is stabilized by C—H(...)O and C—H(...)Cl inter­actions.

Related literature

For ring puckering parameters, see: Cremer & Pople (1975 [triangle]); Nardelli (1983 [triangle]). For the pharmacological properties of piperidin-4-ones, see: El-Subbagh, Abu-Zaid, Mahran, Badria & Al-obaid (2000 [triangle]); Ganellin & Spickett (1965 [triangle]); Hagenbach & Gysin (1952 [triangle]); Jerom & Spencer (1988 [triangle]); Katritzky & Fan (1990 [triangle]); Mobio et al. (1989 [triangle]); Perumal et al. (2001 [triangle]).

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Object name is e-65-o2883-scheme1.jpg

Experimental

Crystal data

  • C22H24ClNO4
  • M r = 401.87
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2883-efi1.jpg
  • a = 8.9147 (8) Å
  • b = 11.9648 (10) Å
  • c = 19.1365 (16) Å
  • α = 99.729 (5)°
  • β = 93.665 (5)°
  • γ = 90.112 (6)°
  • V = 2007.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 293 K
  • 0.15 × 0.15 × 0.14 mm

Data collection

  • Bruker Kappa APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001 [triangle]) T min = 0.968, T max = 0.970
  • 37036 measured reflections
  • 9971 independent reflections
  • 5739 reflections with I > 2σ(I)
  • R int = 0.043

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.164
  • S = 1.05
  • 9971 reflections
  • 512 parameters
  • H-atom parameters constrained
  • Δρmax = 0.49 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043281/bt5090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043281/bt5090Isup2.hkl

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

Acknowledgments

KR thanks the GNR X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the management of Kandaswami Kandar’s College, Velur, Namakkal, TN, India, for the encouragement to pursue the programme.

supplementary crystallographic information

Comment

In the family of heterocyclic compounds, nitrogen containing heterocycles especially piperidin-4-ones presumably gaining considerable importance owing to their varied biological properties such as antiviral, antitumour (El-Subbagh et al., 2000), analgesic (Jerom et al., 1988), local anaesthetic (Perumal et al., 2001; Hagenbach & Gysin, 1952), antimicrobial, bactericidal, fungicidal, herbicidal, insecticidal, antihistaminic, anti-inflammatory, anticancer, CNS stimulant and depressant activities (Mobio et al., 1989; Katritzky & Fan, 1990; Ganellin & Spickett, 1965). In view of these importance and to ascertain the molecular conformation, a crystallographic study of the title compound has been carried out.

The ORTEP diagram of the title compound is shown in Fig.1. There are two crystallographically independent molecules in the asymmetric unit. The piperidine ring in both the molecules adopts a distorted boat conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: for molecule A: q2 = 0.654 (3) Å, q3 = -0.071 (2) Å, [var phi]2 = 248.9 (2)° and Δs(C2A & C5A)= 9.6 (2)°; for molecule B: q2 = 0.655 (3) Å, q3 = 0.065 (3) Å, [var phi]2 = 69.3 (2)° and Δs(C2B & C5B)= 10.0 (2)°. The sum of the bond angles around N atoms [N1A(358.2°) & N1B(357.9°)] of the piperidine ring in both the molecules are accordance with sp2 hybridization. One of the methoxy phenyl rings in both the molecules are approaximately orthogonal to the piperidine ring, which is evident from the interplanar angles of 87.6 (1)° & 88.3 (1)°, whereas the other rings are twisted by 76.3 (1) ° & 74.4 (1) °, respectively. The chloroacetyl group in each molecule is in extended conformation as can be seen from the torsion angles N1A—C7A—C8A—Cl1A (-179.7 (2)°) and N1B—C7B—C8B—Cl1B (-177.7 (1) °).

The crystal packing is stabilized by C—H···O and C—H···Cl interactions, which link the molecules into a chain extending along a–axis. Atoms C6A and C6B of the molecules at (x, y, z) donate one proton each to atoms O1B and O1A of the molecules at (x + 1, y, z) and (x, y, z), respectively, forming a C5 zig–zag chain running along a–axis.

Experimental

To a solution of r-2,c-6-bis(4-methoxyphenyl)-t-3-methylpiperidin-4-one (1.625 g) in anhydrous benzene (60 ml) was added triethylamine (2.78 ml) and Chloroacetylchloride (1.59 ml). The reaction mixture was allowed to stirr at room temperature for 2hrs. The resulting solution was washed with sodium bicarbonate solution (10%), water and the organic layer was dried over anhydrous sodium sulfate, evaporated and crystallized from benzene: pet- ether (60–80°C) in the ratio of 95:05.

Refinement

H atoms were positioned geometrically (C—H=0.93–0.98 Å) and allowed to ride on their parent atoms, with 1.5Ueq(C) for methyl H and 1.2 Ueq(C) for other H atoms.

Figures

Fig. 1.
Perspective view of one of the two molecules in the asymmetric unit of the title compound showing displacement ellipsoids at 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
The crystal packing of the molecules viewed down b–axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C22H24ClNO4Z = 4
Mr = 401.87F(000) = 848
Triclinic, P1Dx = 1.330 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9147 (8) ÅCell parameters from 4567 reflections
b = 11.9648 (10) Åθ = 1.1–28.4°
c = 19.1365 (16) ŵ = 0.22 mm1
α = 99.729 (5)°T = 293 K
β = 93.665 (5)°Block, colorless
γ = 90.112 (6)°0.15 × 0.15 × 0.14 mm
V = 2007.5 (3) Å3

Data collection

Bruker Kappa APEXII area-detector diffractometer9971 independent reflections
Radiation source: fine-focus sealed tube5739 reflections with I > 2σ(I)
graphiteRint = 0.043
ω and [var phi] scansθmax = 28.4°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)h = −11→11
Tmin = 0.968, Tmax = 0.970k = −15→15
37036 measured reflectionsl = −25→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.164w = 1/[σ2(Fo2) + (0.0715P)2 + 0.4246P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
9971 reflectionsΔρmax = 0.49 e Å3
512 parametersΔρmin = −0.37 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0045 (11)

Special details

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)

xyzUiso*/Ueq
Cl1A0.69594 (8)0.10702 (6)0.06473 (4)0.0702 (2)
O1A0.65647 (19)0.09415 (15)0.21138 (9)0.0626 (5)
O2A0.7515 (2)−0.36334 (16)0.42043 (11)0.0770 (6)
O3A1.2325 (2)0.12592 (16)0.38722 (10)0.0706 (5)
O4A1.1117 (2)−0.44641 (14)0.05999 (10)0.0697 (5)
N1A0.8822 (2)0.02377 (14)0.24329 (9)0.0446 (4)
C2A0.8500 (3)0.04894 (19)0.31906 (12)0.0494 (5)
H2A0.75560.09080.32140.059*
C3A0.9715 (3)0.1301 (2)0.35698 (14)0.0578 (6)
H3A0.96390.20090.33880.069*
H3B0.95410.14630.40720.069*
C4A1.1273 (3)0.08538 (18)0.34847 (13)0.0512 (6)
C5A1.1443 (2)−0.01490 (19)0.29002 (13)0.0497 (5)
H5A1.1169−0.08240.30940.060*
C6A1.0360 (2)−0.01290 (17)0.22340 (12)0.0449 (5)
H6A1.07590.04280.19710.054*
C7A0.7816 (3)0.06039 (18)0.19605 (12)0.0475 (5)
C8A0.8334 (3)0.0573 (2)0.12192 (13)0.0605 (6)
H8A0.8585−0.01990.10220.073*
H8B0.92380.10360.12470.073*
C9A0.8240 (2)−0.05747 (19)0.35050 (11)0.0453 (5)
C10A0.7107 (3)−0.1336 (2)0.32057 (13)0.0574 (6)
H10A0.6485−0.11670.28290.069*
C11A0.6880 (3)−0.2336 (2)0.34529 (14)0.0631 (7)
H11A0.6117−0.28350.32410.076*
C12A0.7778 (3)−0.2598 (2)0.40118 (13)0.0563 (6)
C13A0.8878 (3)−0.1850 (2)0.43326 (13)0.0579 (6)
H13A0.9478−0.20140.47170.070*
C14A0.9092 (3)−0.0844 (2)0.40798 (12)0.0551 (6)
H14A0.9833−0.03360.43050.066*
C15A0.8486 (4)−0.3965 (3)0.47465 (18)0.0905 (10)
H15A0.9501−0.39840.46060.136*
H15B0.8193−0.47060.48230.136*
H15C0.8420−0.34320.51780.136*
C16A1.3063 (3)−0.0307 (3)0.27004 (17)0.0746 (8)
H16A1.33290.02670.24340.112*
H16B1.3165−0.10420.24170.112*
H16C1.3716−0.02460.31240.112*
C17A1.0383 (2)−0.12792 (17)0.17620 (11)0.0420 (5)
C18A1.1144 (3)−0.1434 (2)0.11456 (13)0.0537 (6)
H18A1.1528−0.08060.09860.064*
C19A1.1343 (3)−0.2505 (2)0.07620 (13)0.0564 (6)
H19A1.1851−0.25910.03470.068*
C20A1.0794 (3)−0.34451 (19)0.09928 (12)0.0498 (5)
C21A0.9971 (3)−0.33057 (19)0.15832 (13)0.0544 (6)
H21A0.9544−0.39320.17270.065*
C22A0.9780 (3)−0.22299 (19)0.19627 (13)0.0506 (5)
H22A0.9230−0.21460.23650.061*
C23A1.0734 (4)−0.5463 (2)0.08604 (16)0.0838 (9)
H23A1.1205−0.54390.13280.126*
H23B1.1075−0.61150.05490.126*
H23C0.9663−0.55110.08800.126*
Cl1B0.18993 (8)0.15752 (6)0.06531 (4)0.0739 (2)
O1B0.15794 (18)0.24812 (15)0.21225 (9)0.0618 (5)
O2B0.2506 (2)0.81846 (16)0.42158 (11)0.0777 (6)
O3B0.7357 (2)0.31515 (16)0.38623 (10)0.0720 (5)
O4B0.5886 (3)0.70404 (15)0.05185 (10)0.0773 (6)
N1B0.38311 (19)0.33705 (14)0.24239 (10)0.0452 (4)
C2B0.3520 (3)0.35249 (19)0.31822 (12)0.0491 (5)
H2B0.25800.31130.32100.059*
C3B0.4754 (3)0.2927 (2)0.35614 (14)0.0587 (6)
H3C0.45910.30420.40650.070*
H3D0.46800.21190.33830.070*
C4B0.6295 (3)0.33301 (19)0.34681 (13)0.0531 (6)
C5B0.6454 (2)0.40160 (19)0.28828 (13)0.0512 (6)
H5B0.61760.47940.30760.061*
C6B0.5369 (2)0.36252 (18)0.22178 (12)0.0462 (5)
H6B0.57640.29250.19550.055*
C7B0.2822 (3)0.27392 (17)0.19570 (12)0.0472 (5)
C8B0.3329 (3)0.2340 (2)0.12212 (13)0.0582 (6)
H8C0.41990.18600.12510.070*
H8D0.36300.29910.10200.070*
C9B0.3264 (2)0.47558 (19)0.35026 (11)0.0460 (5)
C10B0.2110 (3)0.5346 (2)0.32129 (13)0.0567 (6)
H10B0.14810.49680.28410.068*
C11B0.1870 (3)0.6480 (2)0.34620 (14)0.0630 (7)
H11B0.10930.68570.32550.076*
C12B0.2780 (3)0.7051 (2)0.40158 (13)0.0571 (6)
C13B0.3896 (3)0.6475 (2)0.43301 (13)0.0592 (6)
H13B0.44970.68470.47140.071*
C14B0.4119 (3)0.5341 (2)0.40725 (13)0.0559 (6)
H14B0.48730.49600.42920.067*
C15B0.3483 (4)0.8816 (3)0.47489 (19)0.0936 (10)
H15D0.34160.85300.51860.140*
H15E0.32020.95990.48170.140*
H15F0.44970.87470.46070.140*
C16B0.8068 (3)0.4073 (3)0.26829 (17)0.0766 (8)
H16D0.87200.42530.31060.115*
H16E0.81650.46500.23950.115*
H16F0.83390.33540.24210.115*
C17B0.5366 (2)0.45185 (17)0.17413 (12)0.0442 (5)
C18B0.6123 (3)0.4349 (2)0.11269 (13)0.0562 (6)
H18B0.65450.36450.09790.067*
C19B0.6272 (3)0.5191 (2)0.07250 (14)0.0610 (6)
H19B0.67780.50500.03100.073*
C20B0.5665 (3)0.6245 (2)0.09421 (13)0.0531 (6)
C21B0.4870 (3)0.6429 (2)0.15428 (14)0.0560 (6)
H21B0.44290.71280.16840.067*
C22B0.4730 (3)0.55669 (19)0.19369 (13)0.0513 (6)
H22B0.41950.56990.23440.062*
C23B0.5585 (4)0.8176 (2)0.08017 (17)0.0823 (9)
H23D0.45280.82580.08620.124*
H23E0.58890.86600.04830.124*
H23F0.61340.83830.12540.124*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.0836 (5)0.0706 (4)0.0615 (4)0.0252 (3)0.0072 (3)0.0245 (3)
O1A0.0493 (10)0.0767 (12)0.0659 (11)0.0196 (8)0.0120 (8)0.0209 (9)
O2A0.0729 (12)0.0712 (12)0.0928 (14)−0.0160 (10)−0.0030 (11)0.0344 (11)
O3A0.0686 (12)0.0707 (12)0.0683 (12)−0.0169 (9)−0.0010 (10)0.0023 (9)
O4A0.0953 (14)0.0449 (9)0.0646 (11)0.0087 (9)0.0128 (10)−0.0055 (8)
N1A0.0456 (10)0.0415 (9)0.0482 (11)0.0085 (8)0.0088 (8)0.0096 (8)
C2A0.0477 (13)0.0493 (12)0.0506 (13)0.0117 (10)0.0096 (10)0.0045 (10)
C3A0.0674 (16)0.0426 (12)0.0602 (15)0.0061 (11)0.0056 (12)−0.0012 (11)
C4A0.0565 (14)0.0390 (11)0.0591 (14)−0.0064 (10)0.0023 (11)0.0121 (10)
C5A0.0453 (12)0.0427 (12)0.0615 (14)0.0036 (9)0.0046 (11)0.0092 (10)
C6A0.0423 (12)0.0388 (11)0.0557 (13)0.0040 (9)0.0111 (10)0.0112 (9)
C7A0.0490 (13)0.0394 (11)0.0559 (14)0.0040 (9)0.0086 (11)0.0114 (10)
C8A0.0552 (14)0.0681 (16)0.0647 (16)0.0121 (12)0.0104 (12)0.0272 (13)
C9A0.0417 (12)0.0519 (12)0.0427 (12)0.0065 (9)0.0106 (9)0.0063 (10)
C10A0.0425 (13)0.0775 (17)0.0544 (14)−0.0012 (11)−0.0010 (11)0.0193 (13)
C11A0.0517 (14)0.0775 (18)0.0613 (16)−0.0163 (13)−0.0013 (12)0.0173 (13)
C12A0.0520 (14)0.0608 (15)0.0587 (15)−0.0044 (11)0.0087 (12)0.0158 (12)
C13A0.0590 (15)0.0670 (16)0.0490 (14)−0.0031 (12)−0.0023 (11)0.0158 (12)
C14A0.0587 (15)0.0570 (14)0.0477 (13)−0.0064 (11)−0.0011 (11)0.0053 (11)
C15A0.101 (2)0.085 (2)0.096 (2)−0.0094 (18)−0.0058 (19)0.0486 (19)
C16A0.0462 (14)0.0823 (19)0.090 (2)0.0076 (13)0.0011 (14)0.0000 (16)
C17A0.0397 (11)0.0389 (11)0.0479 (12)0.0058 (8)0.0077 (9)0.0069 (9)
C18A0.0614 (15)0.0453 (12)0.0576 (15)0.0022 (10)0.0159 (12)0.0131 (11)
C19A0.0677 (16)0.0535 (14)0.0495 (14)0.0022 (11)0.0180 (12)0.0073 (11)
C20A0.0561 (14)0.0437 (12)0.0476 (13)0.0075 (10)0.0035 (11)0.0023 (10)
C21A0.0629 (15)0.0389 (12)0.0624 (15)−0.0046 (10)0.0107 (12)0.0086 (10)
C22A0.0529 (13)0.0452 (12)0.0551 (14)−0.0002 (10)0.0176 (11)0.0074 (10)
C23A0.132 (3)0.0422 (14)0.0745 (19)0.0136 (15)−0.0016 (18)0.0047 (13)
Cl1B0.0847 (5)0.0642 (4)0.0679 (4)−0.0272 (3)0.0132 (4)−0.0059 (3)
O1B0.0498 (10)0.0651 (11)0.0693 (11)−0.0137 (8)0.0118 (8)0.0053 (8)
O2B0.0761 (13)0.0598 (11)0.0915 (14)0.0171 (9)−0.0023 (11)−0.0006 (10)
O3B0.0679 (12)0.0776 (12)0.0729 (12)0.0189 (9)−0.0030 (10)0.0221 (10)
O4B0.1166 (16)0.0590 (11)0.0629 (11)−0.0122 (11)0.0186 (11)0.0247 (9)
N1B0.0441 (10)0.0406 (9)0.0524 (11)−0.0041 (7)0.0094 (8)0.0097 (8)
C2B0.0477 (13)0.0494 (12)0.0535 (14)−0.0056 (10)0.0096 (10)0.0164 (10)
C3B0.0702 (16)0.0482 (13)0.0621 (15)−0.0013 (11)0.0054 (13)0.0214 (11)
C4B0.0587 (14)0.0409 (12)0.0597 (15)0.0095 (10)0.0025 (12)0.0091 (10)
C5B0.0459 (13)0.0451 (12)0.0640 (15)0.0017 (10)0.0046 (11)0.0131 (11)
C6B0.0421 (12)0.0402 (11)0.0577 (14)−0.0005 (9)0.0108 (10)0.0098 (10)
C7B0.0478 (13)0.0349 (10)0.0596 (14)0.0001 (9)0.0083 (11)0.0082 (10)
C8B0.0526 (14)0.0541 (14)0.0656 (16)−0.0057 (11)0.0119 (12)0.0008 (12)
C9B0.0411 (12)0.0550 (13)0.0445 (12)−0.0024 (10)0.0120 (9)0.0124 (10)
C10B0.0422 (13)0.0705 (16)0.0555 (14)0.0039 (11)0.0018 (11)0.0057 (12)
C11B0.0536 (14)0.0705 (17)0.0635 (16)0.0189 (12)0.0004 (12)0.0082 (13)
C12B0.0514 (14)0.0604 (15)0.0599 (15)0.0098 (11)0.0110 (12)0.0083 (12)
C13B0.0601 (15)0.0618 (15)0.0520 (14)0.0022 (12)−0.0016 (12)0.0013 (12)
C14B0.0571 (14)0.0602 (15)0.0517 (14)0.0078 (11)0.0001 (11)0.0145 (11)
C15B0.101 (2)0.0663 (19)0.101 (2)0.0106 (17)−0.009 (2)−0.0164 (17)
C16B0.0470 (15)0.097 (2)0.090 (2)−0.0051 (14)0.0015 (14)0.0308 (17)
C17B0.0413 (11)0.0410 (11)0.0517 (13)−0.0035 (9)0.0083 (10)0.0096 (9)
C18B0.0637 (15)0.0447 (12)0.0604 (15)−0.0017 (11)0.0162 (12)0.0052 (11)
C19B0.0740 (17)0.0560 (15)0.0542 (15)−0.0080 (12)0.0215 (12)0.0062 (12)
C20B0.0623 (15)0.0493 (13)0.0499 (13)−0.0106 (11)0.0033 (11)0.0150 (11)
C21B0.0631 (15)0.0436 (12)0.0641 (16)0.0052 (11)0.0088 (12)0.0153 (11)
C22B0.0534 (13)0.0483 (13)0.0555 (14)0.0037 (10)0.0158 (11)0.0137 (11)
C23B0.104 (2)0.0595 (17)0.091 (2)−0.0104 (16)0.0120 (18)0.0324 (16)

Geometric parameters (Å, °)

Cl1A—C8A1.762 (2)Cl1B—C8B1.768 (2)
O1A—C7A1.223 (3)O1B—C7B1.225 (3)
O2A—C12A1.375 (3)O2B—C12B1.372 (3)
O2A—C15A1.417 (4)O2B—C15B1.412 (4)
O3A—C4A1.205 (3)O3B—C4B1.215 (3)
O4A—C20A1.362 (3)O4B—C20B1.372 (3)
O4A—C23A1.420 (3)O4B—C23B1.408 (4)
N1A—C7A1.359 (3)N1B—C7B1.358 (3)
N1A—C2A1.477 (3)N1B—C2B1.476 (3)
N1A—C6A1.494 (3)N1B—C6B1.496 (3)
C2A—C3A1.517 (3)C2B—C9B1.520 (3)
C2A—C9A1.521 (3)C2B—C3B1.525 (3)
C2A—H2A0.9800C2B—H2B0.9800
C3A—C4A1.499 (3)C3B—C4B1.486 (3)
C3A—H3A0.9700C3B—H3C0.9700
C3A—H3B0.9700C3B—H3D0.9700
C4A—C5A1.511 (3)C4B—C5B1.510 (3)
C5A—C16A1.521 (3)C5B—C16B1.516 (3)
C5A—C6A1.553 (3)C5B—C6B1.553 (3)
C5A—H5A0.9800C5B—H5B0.9800
C6A—C17A1.514 (3)C6B—C17B1.518 (3)
C6A—H6A0.9800C6B—H6B0.9800
C7A—C8A1.515 (3)C7B—C8B1.507 (3)
C8A—H8A0.9700C8B—H8C0.9700
C8A—H8B0.9700C8B—H8D0.9700
C9A—C14A1.380 (3)C9B—C14B1.376 (3)
C9A—C10A1.387 (3)C9B—C10B1.388 (3)
C10A—C11A1.378 (4)C10B—C11B1.382 (4)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.374 (3)C11B—C12B1.376 (4)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.369 (3)C12B—C13B1.375 (3)
C13A—C14A1.388 (3)C13B—C14B1.383 (3)
C13A—H13A0.9300C13B—H13B0.9300
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9600C15B—H15D0.9600
C15A—H15B0.9600C15B—H15E0.9600
C15A—H15C0.9600C15B—H15F0.9600
C16A—H16A0.9600C16B—H16D0.9600
C16A—H16B0.9600C16B—H16E0.9600
C16A—H16C0.9600C16B—H16F0.9600
C17A—C22A1.379 (3)C17B—C18B1.379 (3)
C17A—C18A1.384 (3)C17B—C22B1.380 (3)
C18A—C19A1.383 (3)C18B—C19B1.378 (3)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.376 (3)C19B—C20B1.382 (4)
C19A—H19A0.9300C19B—H19B0.9300
C20A—C21A1.373 (3)C20B—C21B1.375 (3)
C21A—C22A1.383 (3)C21B—C22B1.387 (3)
C21A—H21A0.9300C21B—H21B0.9300
C22A—H22A0.9300C22B—H22B0.9300
C23A—H23A0.9600C23B—H23D0.9600
C23A—H23B0.9600C23B—H23E0.9600
C23A—H23C0.9600C23B—H23F0.9600
C12A—O2A—C15A117.9 (2)C12B—O2B—C15B118.1 (2)
C20A—O4A—C23A118.0 (2)C20B—O4B—C23B117.1 (2)
C7A—N1A—C2A117.15 (18)C7B—N1B—C2B116.88 (17)
C7A—N1A—C6A121.55 (18)C7B—N1B—C6B121.37 (18)
C2A—N1A—C6A119.48 (17)C2B—N1B—C6B119.69 (17)
N1A—C2A—C3A107.47 (19)N1B—C2B—C9B113.03 (17)
N1A—C2A—C9A112.76 (17)N1B—C2B—C3B107.54 (19)
C3A—C2A—C9A116.32 (19)C9B—C2B—C3B115.62 (19)
N1A—C2A—H2A106.6N1B—C2B—H2B106.7
C3A—C2A—H2A106.6C9B—C2B—H2B106.7
C9A—C2A—H2A106.6C3B—C2B—H2B106.7
C4A—C3A—C2A113.41 (19)C4B—C3B—C2B113.53 (19)
C4A—C3A—H3A108.9C4B—C3B—H3C108.9
C2A—C3A—H3A108.9C2B—C3B—H3C108.9
C4A—C3A—H3B108.9C4B—C3B—H3D108.9
C2A—C3A—H3B108.9C2B—C3B—H3D108.9
H3A—C3A—H3B107.7H3C—C3B—H3D107.7
O3A—C4A—C3A121.6 (2)O3B—C4B—C3B121.3 (2)
O3A—C4A—C5A122.0 (2)O3B—C4B—C5B122.0 (2)
C3A—C4A—C5A116.36 (19)C3B—C4B—C5B116.6 (2)
C4A—C5A—C16A112.2 (2)C4B—C5B—C16B112.1 (2)
C4A—C5A—C6A113.58 (18)C4B—C5B—C6B113.52 (18)
C16A—C5A—C6A111.3 (2)C16B—C5B—C6B111.3 (2)
C4A—C5A—H5A106.4C4B—C5B—H5B106.5
C16A—C5A—H5A106.4C16B—C5B—H5B106.5
C6A—C5A—H5A106.4C6B—C5B—H5B106.5
N1A—C6A—C17A113.52 (17)N1B—C6B—C17B112.70 (17)
N1A—C6A—C5A111.62 (18)N1B—C6B—C5B111.29 (18)
C17A—C6A—C5A108.61 (17)C17B—C6B—C5B108.99 (17)
N1A—C6A—H6A107.6N1B—C6B—H6B107.9
C17A—C6A—H6A107.6C17B—C6B—H6B107.9
C5A—C6A—H6A107.6C5B—C6B—H6B107.9
O1A—C7A—N1A123.0 (2)O1B—C7B—N1B122.5 (2)
O1A—C7A—C8A121.1 (2)O1B—C7B—C8B121.2 (2)
N1A—C7A—C8A115.8 (2)N1B—C7B—C8B116.25 (19)
C7A—C8A—Cl1A112.47 (17)C7B—C8B—Cl1B112.11 (16)
C7A—C8A—H8A109.1C7B—C8B—H8C109.2
Cl1A—C8A—H8A109.1Cl1B—C8B—H8C109.2
C7A—C8A—H8B109.1C7B—C8B—H8D109.2
Cl1A—C8A—H8B109.1Cl1B—C8B—H8D109.2
H8A—C8A—H8B107.8H8C—C8B—H8D107.9
C14A—C9A—C10A116.9 (2)C14B—C9B—C10B116.8 (2)
C14A—C9A—C2A123.3 (2)C14B—C9B—C2B123.9 (2)
C10A—C9A—C2A119.7 (2)C10B—C9B—C2B119.4 (2)
C11A—C10A—C9A121.6 (2)C11B—C10B—C9B121.8 (2)
C11A—C10A—H10A119.2C11B—C10B—H10B119.1
C9A—C10A—H10A119.2C9B—C10B—H10B119.1
C12A—C11A—C10A120.2 (2)C12B—C11B—C10B119.9 (2)
C12A—C11A—H11A119.9C12B—C11B—H11B120.0
C10A—C11A—H11A119.9C10B—C11B—H11B120.0
C13A—C12A—C11A119.7 (2)O2B—C12B—C13B124.1 (2)
C13A—C12A—O2A124.0 (2)O2B—C12B—C11B116.5 (2)
C11A—C12A—O2A116.3 (2)C13B—C12B—C11B119.4 (2)
C12A—C13A—C14A119.5 (2)C12B—C13B—C14B119.8 (2)
C12A—C13A—H13A120.3C12B—C13B—H13B120.1
C14A—C13A—H13A120.3C14B—C13B—H13B120.1
C9A—C14A—C13A122.1 (2)C9B—C14B—C13B122.2 (2)
C9A—C14A—H14A119.0C9B—C14B—H14B118.9
C13A—C14A—H14A119.0C13B—C14B—H14B118.9
O2A—C15A—H15A109.5O2B—C15B—H15D109.5
O2A—C15A—H15B109.5O2B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
O2A—C15A—H15C109.5O2B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C5A—C16A—H16A109.5C5B—C16B—H16D109.5
C5A—C16A—H16B109.5C5B—C16B—H16E109.5
H16A—C16A—H16B109.5H16D—C16B—H16E109.5
C5A—C16A—H16C109.5C5B—C16B—H16F109.5
H16A—C16A—H16C109.5H16D—C16B—H16F109.5
H16B—C16A—H16C109.5H16E—C16B—H16F109.5
C22A—C17A—C18A117.4 (2)C18B—C17B—C22B117.4 (2)
C22A—C17A—C6A121.5 (2)C18B—C17B—C6B120.8 (2)
C18A—C17A—C6A120.81 (19)C22B—C17B—C6B121.5 (2)
C19A—C18A—C17A121.2 (2)C19B—C18B—C17B121.9 (2)
C19A—C18A—H18A119.4C19B—C18B—H18B119.0
C17A—C18A—H18A119.4C17B—C18B—H18B119.0
C20A—C19A—C18A120.2 (2)C18B—C19B—C20B119.7 (2)
C20A—C19A—H19A119.9C18B—C19B—H19B120.2
C18A—C19A—H19A119.9C20B—C19B—H19B120.2
O4A—C20A—C21A124.9 (2)O4B—C20B—C21B124.4 (2)
O4A—C20A—C19A115.7 (2)O4B—C20B—C19B116.0 (2)
C21A—C20A—C19A119.4 (2)C21B—C20B—C19B119.6 (2)
C20A—C21A—C22A119.7 (2)C20B—C21B—C22B119.6 (2)
C20A—C21A—H21A120.1C20B—C21B—H21B120.2
C22A—C21A—H21A120.1C22B—C21B—H21B120.2
C17A—C22A—C21A121.9 (2)C17B—C22B—C21B121.7 (2)
C17A—C22A—H22A119.1C17B—C22B—H22B119.1
C21A—C22A—H22A119.1C21B—C22B—H22B119.1
O4A—C23A—H23A109.5O4B—C23B—H23D109.5
O4A—C23A—H23B109.5O4B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
O4A—C23A—H23C109.5O4B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C7A—N1A—C2A—C3A−114.3 (2)C7B—N1B—C2B—C9B−116.8 (2)
C6A—N1A—C2A—C3A50.6 (2)C6B—N1B—C2B—C9B79.3 (2)
C7A—N1A—C2A—C9A116.2 (2)C7B—N1B—C2B—C3B114.3 (2)
C6A—N1A—C2A—C9A−78.9 (2)C6B—N1B—C2B—C3B−49.6 (2)
N1A—C2A—C3A—C4A−57.1 (3)N1B—C2B—C3B—C4B56.5 (3)
C9A—C2A—C3A—C4A70.4 (3)C9B—C2B—C3B—C4B−70.9 (3)
C2A—C3A—C4A—O3A−162.9 (2)C2B—C3B—C4B—O3B162.0 (2)
C2A—C3A—C4A—C5A15.6 (3)C2B—C3B—C4B—C5B−15.2 (3)
O3A—C4A—C5A—C16A−19.6 (3)O3B—C4B—C5B—C16B20.4 (3)
C3A—C4A—C5A—C16A161.9 (2)C3B—C4B—C5B—C16B−162.4 (2)
O3A—C4A—C5A—C6A−146.9 (2)O3B—C4B—C5B—C6B147.6 (2)
C3A—C4A—C5A—C6A34.7 (3)C3B—C4B—C5B—C6B−35.2 (3)
C7A—N1A—C6A—C17A−74.5 (2)C7B—N1B—C6B—C17B75.1 (2)
C2A—N1A—C6A—C17A121.3 (2)C2B—N1B—C6B—C17B−121.8 (2)
C7A—N1A—C6A—C5A162.34 (18)C7B—N1B—C6B—C5B−162.16 (19)
C2A—N1A—C6A—C5A−1.9 (2)C2B—N1B—C6B—C5B1.0 (3)
C4A—C5A—C6A—N1A−41.6 (2)C4B—C5B—C6B—N1B42.3 (3)
C16A—C5A—C6A—N1A−169.42 (19)C16B—C5B—C6B—N1B169.9 (2)
C4A—C5A—C6A—C17A−167.52 (18)C4B—C5B—C6B—C17B167.23 (19)
C16A—C5A—C6A—C17A64.7 (2)C16B—C5B—C6B—C17B−65.2 (2)
C2A—N1A—C7A—O1A−13.2 (3)C2B—N1B—C7B—O1B13.3 (3)
C6A—N1A—C7A—O1A−177.7 (2)C6B—N1B—C7B—O1B176.9 (2)
C2A—N1A—C7A—C8A166.74 (19)C2B—N1B—C7B—C8B−165.06 (19)
C6A—N1A—C7A—C8A2.2 (3)C6B—N1B—C7B—C8B−1.5 (3)
O1A—C7A—C8A—Cl1A0.2 (3)O1B—C7B—C8B—Cl1B3.9 (3)
N1A—C7A—C8A—Cl1A−179.68 (16)N1B—C7B—C8B—Cl1B−177.72 (16)
N1A—C2A—C9A—C14A121.4 (2)N1B—C2B—C9B—C14B−121.1 (2)
C3A—C2A—C9A—C14A−3.4 (3)C3B—C2B—C9B—C14B3.5 (3)
N1A—C2A—C9A—C10A−57.8 (3)N1B—C2B—C9B—C10B58.8 (3)
C3A—C2A—C9A—C10A177.4 (2)C3B—C2B—C9B—C10B−176.7 (2)
C14A—C9A—C10A—C11A−2.5 (4)C14B—C9B—C10B—C11B2.8 (4)
C2A—C9A—C10A—C11A176.8 (2)C2B—C9B—C10B—C11B−177.0 (2)
C9A—C10A—C11A—C12A0.5 (4)C9B—C10B—C11B—C12B−0.6 (4)
C10A—C11A—C12A—C13A1.4 (4)C15B—O2B—C12B—C13B3.9 (4)
C10A—C11A—C12A—O2A−177.3 (2)C15B—O2B—C12B—C11B−175.7 (3)
C15A—O2A—C12A—C13A−2.9 (4)C10B—C11B—C12B—O2B177.7 (2)
C15A—O2A—C12A—C11A175.8 (3)C10B—C11B—C12B—C13B−1.9 (4)
C11A—C12A—C13A—C14A−1.2 (4)O2B—C12B—C13B—C14B−177.6 (2)
O2A—C12A—C13A—C14A177.4 (2)C11B—C12B—C13B—C14B2.0 (4)
C10A—C9A—C14A—C13A2.6 (4)C10B—C9B—C14B—C13B−2.8 (4)
C2A—C9A—C14A—C13A−176.6 (2)C2B—C9B—C14B—C13B177.1 (2)
C12A—C13A—C14A—C9A−0.8 (4)C12B—C13B—C14B—C9B0.4 (4)
N1A—C6A—C17A—C22A−55.9 (3)N1B—C6B—C17B—C18B−131.7 (2)
C5A—C6A—C17A—C22A68.8 (3)C5B—C6B—C17B—C18B104.2 (2)
N1A—C6A—C17A—C18A130.6 (2)N1B—C6B—C17B—C22B54.4 (3)
C5A—C6A—C17A—C18A−104.6 (2)C5B—C6B—C17B—C22B−69.6 (3)
C22A—C17A—C18A—C19A−2.5 (3)C22B—C17B—C18B—C19B1.1 (3)
C6A—C17A—C18A—C19A171.2 (2)C6B—C17B—C18B—C19B−173.0 (2)
C17A—C18A—C19A—C20A−0.6 (4)C17B—C18B—C19B—C20B0.8 (4)
C23A—O4A—C20A—C21A−7.8 (4)C23B—O4B—C20B—C21B15.2 (4)
C23A—O4A—C20A—C19A172.7 (2)C23B—O4B—C20B—C19B−166.2 (3)
C18A—C19A—C20A—O4A−176.6 (2)C18B—C19B—C20B—O4B178.9 (2)
C18A—C19A—C20A—C21A3.8 (4)C18B—C19B—C20B—C21B−2.4 (4)
O4A—C20A—C21A—C22A176.6 (2)O4B—C20B—C21B—C22B−179.3 (2)
C19A—C20A—C21A—C22A−3.8 (4)C19B—C20B—C21B—C22B2.2 (4)
C18A—C17A—C22A—C21A2.5 (3)C18B—C17B—C22B—C21B−1.4 (3)
C6A—C17A—C22A—C21A−171.2 (2)C6B—C17B—C22B—C21B172.7 (2)
C20A—C21A—C22A—C17A0.7 (4)C20B—C21B—C22B—C17B−0.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3A—H3A···O3B0.972.583.063 (3)111
C6A—H6A···O1Bi0.982.533.350 (3)142
C6B—H6B···O1A0.982.543.363 (3)142
C8A—H8B···Cl1Bi0.972.813.684 (3)150

Symmetry codes: (i) x+1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5090).

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