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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 9| September 2014| Pages o1056-o1057

Crystal structure of 1-cyclo­propane­carbon­yl-3-methyl-2,6-di-p-tolyl­piperidin-4-one

aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Chidambaram, Tamilnadu, India, bDepartment of Physics, SRM University, Ramapuram Campus, Chennai 600 089, India, and cPost Graduate and Research Department of Botany, Pachaiyappa's College, Chennai 600 030, Tamil Nadu, India
*Correspondence e-mail: krishnasamybala56@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 27 July 2014; accepted 14 August 2014; online 30 August 2014)

The title compound, C24H27NO2, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The two mol­ecules have very similar conformations and each exhibits an intra­molecular C—H⋯π inter­action. The central piperidine rings adopt boat conformations and the p-tolyl rings are inclined to the mean plane of the piperidine ring by 71.21 (11) and 89.86 (12)° in mol­ecule A and by 68.01 (12) and 89.33 (12)° in mol­ecule B. The cyclopropanecarbonyl group is oriented at an angle of 68.5 (2)° with respect to the mean plane of the piperidine ring in mol­ecule A and 66.2 (2)° in mol­ecule B. In the crystal, the A and B mol­ecules are linked by C—H⋯O hydrogen bonds, enclosing R21(6) ring motifs, forming ribbons running along the a-axis direction.

1. Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009[Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S. & Jeong, Y. T. (2009). Eur. J. Med. Chem. 44, 577-592.]); Nalanishi et al. (1974[Nalanishi, M., Shiraki, M., Kobayakawa, T. & Kobayashi, R. (1974). Jpn. Patent. 74-3987.]); Michael (2001[Michael, J. P. (2001). The Alkaloids. Chemistry and Biology, Vol. 55, edited by G. A. Cordell, pp. 91-258. New York: Academic Press.]); Pinder (1992[Pinder, A. R. (1992). Nat. Prod. Rep. 9, 491-504.]); Rubiralta et al. (1991[Rubiralta, M., Giralt, E. & Diez, A. (1991). Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives, pp. 225-312. Amsterdam: Elsevier.]). For the crystal structure of the related compound, 2,2-di­chloro-1-(4-eth­oxy­phen­yl)cyclo­propanylpiperidin-1-yl ketone, see: Sun et al. (2006[Sun, N.-B., Shen, D.-L., Zheng, R.-H., Tan, C.-X. & Weng, J.-Q. (2006). Acta Cryst. E62, o5679-o5680.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C24H27NO2

  • Mr = 361.47

  • Triclinic, [P \overline 1]

  • a = 10.494 (3) Å

  • b = 11.464 (2) Å

  • c = 17.425 (3) Å

  • α = 80.265 (15)°

  • β = 86.064 (17)°

  • γ = 89.877 (18)°

  • V = 2061.1 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.25 × 0.22 × 0.19 mm

2.2. Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany.]) Tmin = 0.982, Tmax = 0.986

  • 13683 measured reflections

  • 7267 independent reflections

  • 4028 reflections with I > 2σ(I)

  • Rint = 0.032

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.156

  • S = 0.95

  • 7276 reflections

  • 493 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C7A–C12A and C7B–C12B rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C23A—H23ACg1 0.93 2.86 3.787 (3) 173
C23B—H23BCg2 0.93 2.85 3.777 (3) 173
C5A—H5A⋯O2Bi 0.98 2.41 3.366 (3) 166
C5B—H5B⋯O2A 0.98 2.42 3.381 (3) 166
C19A—H19A⋯O2Bi 0.93 2.59 3.435 (3) 151
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Synthesis and crystallization top

To a well stirred solution of 3-methyl-2,6-di-p-tolyl­piperidin-4-one (1 equiv) and tri­ethyl­amine (1 equiv) in 30 ml of dry benzene, cyclo­propane­carbonyl chloride (1 equiv) in 20 ml of benzene was added drop wise over a period of 30 min. Stirring was continued with mild heating using a magnetic stirrer. After the completion of reaction, it was poured into water and extracted with ether in three 50 ml portions. The combined ether extract was then washed well with 3% sodium bicarbonate solution and dried over anhydrous sodium sulfate. Crystal were obtained by slow evaporation of a solution of the title compound in ethanol.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms were fixed geometrically and allowed to ride on their parent atoms: C—H = 0.93–0.97 Å with Uiso(H) = 1.5Ueq(C-methyl) and = 1.2Ueq(C) for other H atoms.

Related literature top

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009); Nalanishi et al. (1974); Michael (2001); Pinder (1992); Rubiralta et al. (1991). For the crystal structure of the related compound, 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanylpiperidin-1-yl ketone, see: Sun et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the two independent molecules of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the b axis, in which hydrogen bonds form R21(6) bifurcated ring motifs forming ribbons running along a axis. For the sake of clarity, H atoms not involved in hydrogen bonds have been omitted.
1-Cyclopropanecarbonyl-3-methyl-2,6-di-p-tolylpiperidin-4-one top
Crystal data top
C24H27NO2Z = 4
Mr = 361.47F(000) = 776
Triclinic, P1Dx = 1.165 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.494 (3) ÅCell parameters from 7267 reflections
b = 11.464 (2) Åθ = 2.7–25°
c = 17.425 (3) ŵ = 0.07 mm1
α = 80.265 (15)°T = 293 K
β = 86.064 (17)°Block, white crystalline
γ = 89.877 (18)°0.25 × 0.22 × 0.19 mm
V = 2061.1 (7) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7267 independent reflections
Radiation source: fine-focus sealed tube4028 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and ϕ scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.982, Tmax = 0.986k = 1113
13683 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.0688P)2]
where P = (Fo2 + 2Fc2)/3
7276 reflections(Δ/σ)max = 0.011
493 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.14 e Å3
Crystal data top
C24H27NO2γ = 89.877 (18)°
Mr = 361.47V = 2061.1 (7) Å3
Triclinic, P1Z = 4
a = 10.494 (3) ÅMo Kα radiation
b = 11.464 (2) ŵ = 0.07 mm1
c = 17.425 (3) ÅT = 293 K
α = 80.265 (15)°0.25 × 0.22 × 0.19 mm
β = 86.064 (17)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7267 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4028 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.986Rint = 0.032
13683 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 0.95Δρmax = 0.16 e Å3
7276 reflectionsΔρmin = 0.14 e Å3
493 parameters
Special details top

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) top
xyzUiso*/Ueq
C1A0.2419 (2)0.2299 (2)0.33693 (13)0.0591 (6)
H1A0.29130.30400.32740.071*
C1B0.7385 (2)0.3525 (2)0.34051 (14)0.0598 (6)
H1B0.78730.28220.33210.072*
C2A0.1458 (2)0.2385 (2)0.40535 (15)0.0755 (8)
H2A10.18970.22360.45320.091*
H2A20.11370.31880.39960.091*
C2B0.6410 (2)0.3116 (2)0.40856 (15)0.0755 (8)
H2B10.60820.23440.40350.091*
H2B20.68400.30250.45670.091*
C3A0.0349 (3)0.1549 (2)0.41292 (14)0.0699 (8)
C3B0.5316 (3)0.3931 (3)0.41428 (15)0.0722 (8)
C4A0.0335 (2)0.0760 (2)0.35270 (13)0.0553 (6)
H4A0.10210.01850.36300.066*
C4B0.5318 (2)0.5027 (2)0.35287 (13)0.0563 (6)
H4B0.60100.55420.36280.068*
C5A0.06279 (19)0.14576 (18)0.27003 (12)0.0459 (5)
H5A0.01280.19290.25590.055*
C5B0.56099 (18)0.47286 (19)0.27085 (12)0.0475 (5)
H5B0.48480.43400.25700.057*
C6A0.0910 (2)0.0064 (2)0.35850 (16)0.0757 (8)
H6A10.10700.03590.41070.114*
H6A20.08470.04870.32270.114*
H6A30.15990.05990.34580.114*
C6B0.4085 (2)0.5713 (3)0.35773 (16)0.0816 (9)
H6B10.33840.52330.34820.122*
H6B20.41420.64210.31930.122*
H6B30.39500.59190.40880.122*
C7A0.3389 (2)0.1305 (2)0.34870 (14)0.0571 (6)
C7B0.8357 (2)0.4449 (2)0.35131 (13)0.0555 (6)
C8A0.4362 (2)0.1284 (2)0.29136 (15)0.0654 (7)
H8A0.44160.18770.24770.078*
C8B0.9348 (2)0.4739 (2)0.29481 (14)0.0619 (7)
H8B0.94100.43480.25210.074*
C9A0.5255 (2)0.0395 (2)0.29806 (17)0.0743 (8)
H9A0.59060.04110.25890.089*
C9B1.0245 (2)0.5594 (2)0.30002 (16)0.0679 (7)
H9B1.09010.57640.26100.082*
C10A0.5215 (2)0.0512 (2)0.36060 (18)0.0731 (8)
C10B1.0187 (2)0.6200 (2)0.36181 (17)0.0679 (7)
C11A0.4260 (3)0.0472 (3)0.41769 (17)0.0862 (9)
H11A0.42100.10660.46140.103*
C11B0.9221 (3)0.5888 (3)0.41889 (16)0.0809 (8)
H11B0.91660.62670.46210.097*
C12A0.3370 (3)0.0417 (3)0.41257 (15)0.0783 (8)
H12A0.27450.04160.45310.094*
C12B0.8330 (2)0.5025 (3)0.41386 (15)0.0769 (8)
H12B0.76960.48330.45400.092*
C13A0.6162 (3)0.1515 (3)0.3662 (2)0.1086 (11)
H13A0.58240.21520.34410.163*
H13B0.63090.17910.42000.163*
H13C0.69520.12390.33800.163*
C13B1.1129 (2)0.7172 (3)0.3665 (2)0.0964 (10)
H13D1.07150.79240.35630.145*
H13E1.18320.71500.32850.145*
H13F1.14400.70600.41780.145*
C14A0.1987 (2)0.3155 (2)0.20440 (14)0.0529 (6)
C14B0.6965 (2)0.3324 (2)0.20803 (14)0.0531 (6)
C15A0.1157 (2)0.3300 (2)0.13864 (14)0.0601 (6)
H15A0.03750.28170.14550.072*
C15B0.6111 (2)0.3498 (2)0.14333 (13)0.0573 (6)
H15B0.53130.39200.15140.069*
C16A0.1098 (3)0.4497 (2)0.09105 (16)0.0867 (9)
H16A0.02880.47460.07040.104*
H16B0.15980.51230.10600.104*
C16B0.6711 (3)0.3653 (3)0.06201 (15)0.0875 (9)
H16C0.62930.41750.02180.105*
H16D0.76360.36600.05530.105*
C17A0.1782 (3)0.3580 (3)0.05831 (16)0.0987 (10)
H17A0.27070.36330.05290.118*
H17B0.13970.32560.01730.118*
C17B0.6075 (3)0.2534 (2)0.09552 (15)0.0814 (8)
H17C0.66080.18490.10960.098*
H17D0.52640.23630.07600.098*
C18A0.08307 (19)0.06132 (18)0.21231 (13)0.0464 (5)
C18B0.58476 (18)0.58418 (18)0.21128 (13)0.0464 (5)
C19A0.0090 (2)0.0473 (2)0.16252 (14)0.0565 (6)
H19A0.08200.09340.16210.068*
C19B0.4943 (2)0.6257 (2)0.16086 (14)0.0593 (6)
H19B0.41810.58380.16260.071*
C20A0.0054 (2)0.0349 (2)0.11287 (14)0.0651 (7)
H20A0.05830.04240.07940.078*
C20B0.5143 (2)0.7287 (2)0.10750 (15)0.0689 (7)
H20B0.45110.75460.07390.083*
C21A0.1108 (3)0.1056 (2)0.11164 (15)0.0662 (7)
C21B0.6248 (2)0.7937 (2)0.10268 (17)0.0757 (8)
C22A0.2031 (2)0.0902 (2)0.16063 (16)0.0735 (8)
H22A0.27640.13590.16050.088*
C22B0.7141 (2)0.7521 (2)0.15385 (18)0.0873 (9)
H22B0.78990.79450.15270.105*
C23A0.1904 (2)0.0082 (2)0.21062 (14)0.0631 (7)
H23A0.25490.00000.24340.076*
C23B0.6951 (2)0.6490 (2)0.20716 (15)0.0672 (7)
H23B0.75820.62320.24080.081*
C24A0.1234 (3)0.1974 (3)0.05885 (18)0.1032 (11)
H24A0.04360.23890.06070.155*
H24B0.18890.25240.07600.155*
H24C0.14570.15910.00630.155*
C24B0.6486 (3)0.9056 (3)0.0430 (2)0.1278 (14)
H24D0.57990.91620.00880.192*
H24E0.72770.89880.01300.192*
H24F0.65310.97240.06930.192*
N1A0.17108 (15)0.22916 (15)0.26704 (10)0.0496 (5)
N1B0.66769 (15)0.38776 (15)0.27005 (10)0.0493 (5)
O1A0.0479 (2)0.1532 (2)0.46437 (12)0.1125 (8)
O1B0.4475 (2)0.3708 (2)0.46545 (12)0.1167 (8)
O2A0.29081 (15)0.38296 (15)0.20209 (11)0.0766 (5)
O2B0.78989 (15)0.26785 (16)0.20523 (10)0.0792 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0691 (15)0.0556 (15)0.0546 (16)0.0053 (12)0.0155 (12)0.0106 (12)
C1B0.0675 (15)0.0546 (15)0.0560 (16)0.0074 (12)0.0123 (12)0.0021 (12)
C2A0.0923 (19)0.080 (2)0.0613 (18)0.0145 (16)0.0129 (15)0.0281 (15)
C2B0.0910 (19)0.0755 (19)0.0538 (17)0.0197 (15)0.0091 (14)0.0088 (14)
C3A0.0815 (18)0.0777 (19)0.0480 (16)0.0174 (15)0.0027 (14)0.0064 (14)
C3B0.0752 (18)0.091 (2)0.0496 (17)0.0203 (15)0.0045 (14)0.0141 (15)
C4A0.0569 (14)0.0553 (15)0.0496 (15)0.0052 (11)0.0054 (11)0.0007 (12)
C4B0.0530 (13)0.0669 (16)0.0498 (15)0.0043 (11)0.0039 (11)0.0146 (13)
C5A0.0463 (12)0.0448 (13)0.0457 (13)0.0011 (9)0.0007 (10)0.0065 (11)
C5B0.0420 (12)0.0532 (14)0.0487 (14)0.0027 (10)0.0003 (10)0.0138 (11)
C6A0.0624 (15)0.0814 (19)0.0753 (19)0.0104 (13)0.0108 (14)0.0039 (15)
C6B0.0585 (15)0.110 (2)0.083 (2)0.0064 (15)0.0099 (14)0.0417 (18)
C7A0.0594 (14)0.0585 (16)0.0539 (16)0.0055 (11)0.0152 (12)0.0061 (13)
C7B0.0583 (14)0.0611 (15)0.0473 (15)0.0093 (11)0.0104 (11)0.0069 (12)
C8A0.0609 (15)0.0619 (17)0.0667 (17)0.0073 (13)0.0027 (13)0.0076 (13)
C8B0.0599 (15)0.0656 (17)0.0630 (17)0.0120 (12)0.0042 (13)0.0188 (13)
C9A0.0542 (15)0.0771 (19)0.086 (2)0.0043 (13)0.0022 (14)0.0000 (17)
C9B0.0537 (14)0.0768 (19)0.0741 (19)0.0055 (13)0.0004 (13)0.0171 (15)
C10A0.0649 (16)0.0589 (17)0.092 (2)0.0104 (13)0.0176 (15)0.0027 (16)
C10B0.0577 (15)0.0664 (17)0.084 (2)0.0142 (13)0.0157 (14)0.0206 (16)
C11A0.086 (2)0.083 (2)0.077 (2)0.0012 (16)0.0144 (17)0.0248 (16)
C11B0.0786 (19)0.103 (2)0.070 (2)0.0010 (17)0.0097 (16)0.0391 (17)
C12A0.0778 (18)0.097 (2)0.0528 (17)0.0059 (16)0.0081 (13)0.0088 (16)
C12B0.0719 (17)0.107 (2)0.0532 (17)0.0045 (16)0.0018 (13)0.0202 (16)
C13A0.085 (2)0.070 (2)0.166 (3)0.0032 (16)0.020 (2)0.001 (2)
C13B0.0794 (19)0.082 (2)0.136 (3)0.0029 (16)0.0143 (18)0.040 (2)
C14A0.0558 (14)0.0444 (14)0.0570 (16)0.0012 (11)0.0006 (12)0.0053 (12)
C14B0.0526 (13)0.0484 (14)0.0578 (16)0.0002 (11)0.0021 (11)0.0100 (12)
C15A0.0652 (15)0.0558 (16)0.0557 (16)0.0081 (11)0.0087 (12)0.0026 (13)
C15B0.0632 (14)0.0586 (15)0.0526 (15)0.0025 (11)0.0003 (12)0.0186 (12)
C16A0.111 (2)0.0654 (19)0.076 (2)0.0039 (16)0.0194 (17)0.0155 (16)
C16B0.100 (2)0.103 (2)0.0568 (18)0.0139 (18)0.0126 (16)0.0108 (17)
C17A0.110 (2)0.123 (3)0.060 (2)0.006 (2)0.0074 (17)0.0110 (19)
C17B0.106 (2)0.075 (2)0.0696 (19)0.0024 (16)0.0055 (16)0.0301 (16)
C18A0.0457 (12)0.0433 (13)0.0487 (14)0.0048 (10)0.0020 (10)0.0059 (11)
C18B0.0434 (12)0.0448 (13)0.0523 (14)0.0038 (10)0.0021 (10)0.0124 (11)
C19A0.0549 (13)0.0547 (15)0.0610 (16)0.0002 (11)0.0036 (12)0.0128 (13)
C19B0.0542 (13)0.0618 (16)0.0622 (16)0.0004 (11)0.0092 (12)0.0090 (14)
C20A0.0701 (16)0.0656 (17)0.0629 (17)0.0116 (13)0.0086 (13)0.0184 (14)
C20B0.0656 (16)0.0656 (18)0.0734 (19)0.0127 (13)0.0210 (13)0.0009 (15)
C21A0.0795 (18)0.0570 (16)0.0638 (18)0.0051 (14)0.0076 (14)0.0204 (13)
C21B0.0747 (17)0.0571 (17)0.088 (2)0.0014 (14)0.0151 (15)0.0117 (15)
C22A0.0673 (17)0.0725 (19)0.086 (2)0.0148 (13)0.0004 (15)0.0308 (16)
C22B0.0638 (16)0.0688 (19)0.117 (3)0.0151 (13)0.0227 (16)0.0273 (18)
C23A0.0545 (14)0.0678 (17)0.0697 (18)0.0053 (12)0.0036 (12)0.0196 (14)
C23B0.0530 (14)0.0607 (16)0.0824 (19)0.0025 (12)0.0193 (13)0.0092 (14)
C24A0.133 (3)0.085 (2)0.102 (3)0.0090 (19)0.001 (2)0.049 (2)
C24B0.126 (3)0.086 (2)0.153 (3)0.016 (2)0.048 (2)0.050 (2)
N1A0.0550 (11)0.0465 (11)0.0467 (12)0.0049 (8)0.0083 (9)0.0045 (9)
N1B0.0522 (11)0.0483 (11)0.0478 (12)0.0059 (8)0.0029 (9)0.0092 (9)
O1A0.1181 (16)0.147 (2)0.0728 (14)0.0047 (14)0.0338 (13)0.0354 (14)
O1B0.1148 (16)0.150 (2)0.0722 (15)0.0259 (14)0.0368 (13)0.0034 (14)
O2A0.0700 (11)0.0646 (11)0.0909 (14)0.0230 (9)0.0138 (9)0.0031 (10)
O2B0.0688 (11)0.0805 (13)0.0948 (14)0.0267 (10)0.0071 (9)0.0332 (11)
Geometric parameters (Å, º) top
C1A—N1A1.471 (3)C13A—H13A0.9600
C1A—C7A1.523 (3)C13A—H13B0.9600
C1A—C2A1.524 (3)C13A—H13C0.9600
C1A—H1A0.9800C13B—H13D0.9600
C1B—N1B1.476 (3)C13B—H13E0.9600
C1B—C7B1.515 (3)C13B—H13F0.9600
C1B—C2B1.523 (3)C14A—O2A1.233 (2)
C1B—H1B0.9800C14A—O2A1.233 (2)
C2A—C3A1.494 (3)C14A—N1A1.360 (3)
C2A—H2A10.9700C14A—C15A1.473 (3)
C2A—H2A20.9700C14B—O2B1.230 (2)
C2B—C3B1.487 (3)C14B—N1B1.359 (3)
C2B—H2B10.9700C14B—C15B1.475 (3)
C2B—H2B20.9700C15A—C16A1.482 (3)
C3A—O1A1.202 (3)C15A—C17A1.488 (3)
C3A—C4A1.497 (3)C15A—H15A0.9800
C3B—O1B1.206 (3)C15B—C16B1.493 (3)
C3B—C4B1.506 (4)C15B—C17B1.495 (3)
C4A—C6A1.521 (3)C15B—H15B0.9800
C4A—C5A1.536 (3)C16A—C17A1.445 (4)
C4A—H4A0.9800C16A—H16A0.9700
C4B—C6B1.517 (3)C16A—H16B0.9700
C4B—C5B1.536 (3)C16B—C17B1.460 (3)
C4B—H4B0.9800C16B—H16C0.9700
C5A—N1A1.479 (2)C16B—H16D0.9700
C5A—C18A1.514 (3)C17A—H17A0.9700
C5A—H5A0.9800C17A—H17B0.9700
C5B—N1B1.484 (2)C17B—H17C0.9700
C5B—C18B1.512 (3)C17B—H17D0.9700
C5B—H5B0.9800C18A—C19A1.370 (3)
C6A—H6A10.9600C18A—C23A1.380 (3)
C6A—H6A20.9600C18B—C19B1.368 (3)
C6A—H6A30.9600C18B—C23B1.368 (3)
C6B—H6B10.9600C19A—C20A1.384 (3)
C6B—H6B20.9600C19A—H19A0.9300
C6B—H6B30.9600C19B—C20B1.380 (3)
C7A—C12A1.375 (3)C19B—H19B0.9300
C7A—C8A1.382 (3)C20A—C21A1.371 (3)
C7B—C12B1.366 (3)C20A—H20A0.9300
C7B—C8B1.382 (3)C20B—C21B1.370 (3)
C8A—C9A1.379 (3)C20B—H20B0.9300
C8A—H8A0.9300C21A—C22A1.365 (4)
C8B—C9B1.379 (3)C21A—C24A1.510 (3)
C8B—H8B0.9300C21B—C22B1.367 (4)
C9A—C10A1.372 (4)C21B—C24B1.518 (4)
C9A—H9A0.9300C22A—C23A1.386 (3)
C9B—C10B1.374 (3)C22A—H22A0.9300
C9B—H9B0.9300C22B—C23B1.380 (3)
C10A—C11A1.369 (3)C22B—H22B0.9300
C10A—C13A1.513 (4)C23A—H23A0.9300
C10B—C11B1.374 (3)C23B—H23B0.9300
C10B—C13B1.507 (3)C24A—H24A0.9600
C11A—C12A1.376 (3)C24A—H24B0.9600
C11A—H11A0.9300C24A—H24C0.9600
C11B—C12B1.380 (4)C24B—H24D0.9600
C11B—H11B0.9300C24B—H24E0.9600
C12A—H12A0.9300C24B—H24F0.9600
C12B—H12B0.9300
N1A—C1A—C7A112.45 (18)H13A—C13A—H13C109.5
N1A—C1A—C2A108.28 (18)H13B—C13A—H13C109.5
C7A—C1A—C2A116.9 (2)C10B—C13B—H13D109.5
N1A—C1A—H1A106.2C10B—C13B—H13E109.5
C7A—C1A—H1A106.2H13D—C13B—H13E109.5
C2A—C1A—H1A106.2C10B—C13B—H13F109.5
N1B—C1B—C7B112.72 (19)H13D—C13B—H13F109.5
N1B—C1B—C2B107.62 (18)H13E—C13B—H13F109.5
C7B—C1B—C2B117.1 (2)O2A—C14A—N1A121.2 (2)
N1B—C1B—H1B106.2O2A—C14A—N1A121.2 (2)
C7B—C1B—H1B106.2O2A—C14A—C15A119.4 (2)
C2B—C1B—H1B106.2O2A—C14A—C15A119.4 (2)
C3A—C2A—C1A114.4 (2)N1A—C14A—C15A119.3 (2)
C3A—C2A—H2A1108.7O2B—C14B—N1B121.9 (2)
C1A—C2A—H2A1108.7O2B—C14B—C15B119.8 (2)
C3A—C2A—H2A2108.7N1B—C14B—C15B118.29 (19)
C1A—C2A—H2A2108.7C14A—C15A—C16A117.1 (2)
H2A1—C2A—H2A2107.6C14A—C15A—C17A117.6 (2)
C3B—C2B—C1B114.3 (2)C16A—C15A—C17A58.24 (17)
C3B—C2B—H2B1108.7C14A—C15A—H15A117.0
C1B—C2B—H2B1108.7C16A—C15A—H15A117.0
C3B—C2B—H2B2108.7C17A—C15A—H15A117.0
C1B—C2B—H2B2108.7C14B—C15B—C16B117.8 (2)
H2B1—C2B—H2B2107.6C14B—C15B—C17B116.7 (2)
O1A—C3A—C2A121.0 (2)C16B—C15B—C17B58.50 (16)
O1A—C3A—C4A123.0 (3)C14B—C15B—H15B117.0
C2A—C3A—C4A116.00 (19)C16B—C15B—H15B117.0
O1B—C3B—C2B120.9 (3)C17B—C15B—H15B117.0
O1B—C3B—C4B122.6 (3)C17A—C16A—C15A61.10 (18)
C2B—C3B—C4B116.46 (19)C17A—C16A—H16A117.7
C3A—C4A—C6A112.08 (19)C15A—C16A—H16A117.7
C3A—C4A—C5A111.48 (18)C17A—C16A—H16B117.7
C6A—C4A—C5A111.3 (2)C15A—C16A—H16B117.7
C3A—C4A—H4A107.2H16A—C16A—H16B114.8
C6A—C4A—H4A107.2C17B—C16B—C15B60.81 (16)
C5A—C4A—H4A107.2C17B—C16B—H16C117.7
C3B—C4B—C6B112.18 (19)C15B—C16B—H16C117.7
C3B—C4B—C5B111.23 (19)C17B—C16B—H16D117.7
C6B—C4B—C5B111.4 (2)C15B—C16B—H16D117.7
C3B—C4B—H4B107.2H16C—C16B—H16D114.8
C6B—C4B—H4B107.2C16A—C17A—C15A60.66 (17)
C5B—C4B—H4B107.2C16A—C17A—H17A117.7
N1A—C5A—C18A112.76 (15)C15A—C17A—H17A117.7
N1A—C5A—C4A111.62 (18)C16A—C17A—H17B117.7
C18A—C5A—C4A110.06 (17)C15A—C17A—H17B117.7
N1A—C5A—H5A107.4H17A—C17A—H17B114.8
C18A—C5A—H5A107.4C16B—C17B—C15B60.69 (16)
C4A—C5A—H5A107.4C16B—C17B—H17C117.7
N1B—C5B—C18B112.55 (15)C15B—C17B—H17C117.7
N1B—C5B—C4B111.12 (17)C16B—C17B—H17D117.7
C18B—C5B—C4B110.95 (18)C15B—C17B—H17D117.7
N1B—C5B—H5B107.3H17C—C17B—H17D114.8
C18B—C5B—H5B107.3C19A—C18A—C23A117.8 (2)
C4B—C5B—H5B107.3C19A—C18A—C5A120.37 (19)
C4A—C6A—H6A1109.5C23A—C18A—C5A121.8 (2)
C4A—C6A—H6A2109.5C19B—C18B—C23B117.5 (2)
H6A1—C6A—H6A2109.5C19B—C18B—C5B120.83 (19)
C4A—C6A—H6A3109.5C23B—C18B—C5B121.7 (2)
H6A1—C6A—H6A3109.5C18A—C19A—C20A120.7 (2)
H6A2—C6A—H6A3109.5C18A—C19A—H19A119.6
C4B—C6B—H6B1109.5C20A—C19A—H19A119.6
C4B—C6B—H6B2109.5C18B—C19B—C20B121.1 (2)
H6B1—C6B—H6B2109.5C18B—C19B—H19B119.4
C4B—C6B—H6B3109.5C20B—C19B—H19B119.4
H6B1—C6B—H6B3109.5C21A—C20A—C19A121.9 (2)
H6B2—C6B—H6B3109.5C21A—C20A—H20A119.1
C12A—C7A—C8A117.0 (2)C19A—C20A—H20A119.1
C12A—C7A—C1A124.8 (2)C21B—C20B—C19B121.8 (2)
C8A—C7A—C1A118.3 (2)C21B—C20B—H20B119.1
C12B—C7B—C8B116.8 (2)C19B—C20B—H20B119.1
C12B—C7B—C1B124.4 (2)C22A—C21A—C20A117.2 (2)
C8B—C7B—C1B118.8 (2)C22A—C21A—C24A121.5 (3)
C9A—C8A—C7A120.9 (2)C20A—C21A—C24A121.3 (3)
C9A—C8A—H8A119.5C22B—C21B—C20B116.7 (2)
C7A—C8A—H8A119.5C22B—C21B—C24B121.3 (3)
C9B—C8B—C7B121.8 (2)C20B—C21B—C24B122.0 (3)
C9B—C8B—H8B119.1C21A—C22A—C23A121.7 (2)
C7B—C8B—H8B119.1C21A—C22A—H22A119.1
C10A—C9A—C8A122.2 (2)C23A—C22A—H22A119.1
C10A—C9A—H9A118.9C21B—C22B—C23B121.9 (2)
C8A—C9A—H9A118.9C21B—C22B—H22B119.1
C10B—C9B—C8B121.2 (2)C23B—C22B—H22B119.1
C10B—C9B—H9B119.4C18A—C23A—C22A120.7 (2)
C8B—C9B—H9B119.4C18A—C23A—H23A119.6
C11A—C10A—C9A116.4 (3)C22A—C23A—H23A119.6
C11A—C10A—C13A121.4 (3)C18B—C23B—C22B121.1 (2)
C9A—C10A—C13A122.1 (3)C18B—C23B—H23B119.5
C11B—C10B—C9B116.9 (2)C22B—C23B—H23B119.5
C11B—C10B—C13B121.4 (3)C21A—C24A—H24A109.5
C9B—C10B—C13B121.7 (2)C21A—C24A—H24B109.5
C10A—C11A—C12A122.2 (3)H24A—C24A—H24B109.5
C10A—C11A—H11A118.9C21A—C24A—H24C109.5
C12A—C11A—H11A118.9H24A—C24A—H24C109.5
C10B—C11B—C12B121.8 (3)H24B—C24A—H24C109.5
C10B—C11B—H11B119.1C21B—C24B—H24D109.5
C12B—C11B—H11B119.1C21B—C24B—H24E109.5
C7A—C12A—C11A121.2 (2)H24D—C24B—H24E109.5
C7A—C12A—H12A119.4C21B—C24B—H24F109.5
C11A—C12A—H12A119.4H24D—C24B—H24F109.5
C7B—C12B—C11B121.5 (2)H24E—C24B—H24F109.5
C7B—C12B—H12B119.2C14A—N1A—C1A117.82 (18)
C11B—C12B—H12B119.2C14A—N1A—C5A121.97 (19)
C10A—C13A—H13A109.5C1A—N1A—C5A119.75 (17)
C10A—C13A—H13B109.5C14B—N1B—C1B117.74 (18)
H13A—C13A—H13B109.5C14B—N1B—C5B121.91 (19)
C10A—C13A—H13C109.5C1B—N1B—C5B120.12 (16)
N1A—C1A—C2A—C3A47.4 (3)O2B—C14B—C15B—C17B25.2 (3)
C7A—C1A—C2A—C3A80.8 (3)N1B—C14B—C15B—C17B153.8 (2)
N1B—C1B—C2B—C3B47.6 (3)C14A—C15A—C16A—C17A107.2 (2)
C7B—C1B—C2B—C3B80.6 (3)C14B—C15B—C16B—C17B105.9 (3)
C1A—C2A—C3A—O1A179.8 (2)C14A—C15A—C17A—C16A106.3 (3)
C1A—C2A—C3A—C4A0.4 (3)C14B—C15B—C17B—C16B107.6 (2)
C1B—C2B—C3B—O1B179.8 (2)N1A—C5A—C18A—C19A129.1 (2)
C1B—C2B—C3B—C4B0.3 (3)C4A—C5A—C18A—C19A105.6 (2)
O1A—C3A—C4A—C6A7.1 (4)N1A—C5A—C18A—C23A54.4 (3)
C2A—C3A—C4A—C6A172.2 (2)C4A—C5A—C18A—C23A70.9 (2)
O1A—C3A—C4A—C5A132.6 (3)N1B—C5B—C18B—C19B130.0 (2)
C2A—C3A—C4A—C5A46.7 (3)C4B—C5B—C18B—C19B104.7 (2)
O1B—C3B—C4B—C6B6.8 (4)N1B—C5B—C18B—C23B52.0 (3)
C2B—C3B—C4B—C6B172.7 (2)C4B—C5B—C18B—C23B73.2 (2)
O1B—C3B—C4B—C5B132.4 (3)C23A—C18A—C19A—C20A0.6 (3)
C2B—C3B—C4B—C5B47.1 (3)C5A—C18A—C19A—C20A176.07 (19)
C3A—C4A—C5A—N1A44.4 (2)C23B—C18B—C19B—C20B0.5 (3)
C6A—C4A—C5A—N1A170.28 (17)C5B—C18B—C19B—C20B178.6 (2)
C3A—C4A—C5A—C18A170.35 (18)C18A—C19A—C20A—C21A0.4 (4)
C6A—C4A—C5A—C18A63.7 (2)C18B—C19B—C20B—C21B0.1 (4)
C3B—C4B—C5B—N1B43.7 (2)C19A—C20A—C21A—C22A1.2 (4)
C6B—C4B—C5B—N1B169.65 (18)C19A—C20A—C21A—C24A178.2 (2)
C3B—C4B—C5B—C18B169.69 (18)C19B—C20B—C21B—C22B0.5 (4)
C6B—C4B—C5B—C18B64.3 (2)C19B—C20B—C21B—C24B178.6 (3)
N1A—C1A—C7A—C12A118.7 (3)C20A—C21A—C22A—C23A1.1 (4)
C2A—C1A—C7A—C12A7.4 (4)C24A—C21A—C22A—C23A178.3 (2)
N1A—C1A—C7A—C8A61.2 (3)C20B—C21B—C22B—C23B0.8 (5)
C2A—C1A—C7A—C8A172.7 (2)C24B—C21B—C22B—C23B178.4 (3)
N1B—C1B—C7B—C12B118.2 (3)C19A—C18A—C23A—C22A0.7 (3)
C2B—C1B—C7B—C12B7.5 (3)C5A—C18A—C23A—C22A175.9 (2)
N1B—C1B—C7B—C8B61.9 (3)C21A—C22A—C23A—C18A0.1 (4)
C2B—C1B—C7B—C8B172.4 (2)C19B—C18B—C23B—C22B0.2 (4)
C12A—C7A—C8A—C9A1.1 (4)C5B—C18B—C23B—C22B178.3 (2)
C1A—C7A—C8A—C9A178.8 (2)C21B—C22B—C23B—C18B0.4 (4)
C12B—C7B—C8B—C9B1.8 (4)O2A—C14A—N1A—C1A9.3 (3)
C1B—C7B—C8B—C9B178.3 (2)O2A—C14A—N1A—C1A9.3 (3)
C7A—C8A—C9A—C10A0.9 (4)C15A—C14A—N1A—C1A169.75 (18)
C7B—C8B—C9B—C10B0.3 (4)O2A—C14A—N1A—C5A178.56 (18)
C8A—C9A—C10A—C11A1.9 (4)O2A—C14A—N1A—C5A178.56 (18)
C8A—C9A—C10A—C13A177.3 (3)C15A—C14A—N1A—C5A2.4 (3)
C8B—C9B—C10B—C11B2.0 (4)C7A—C1A—N1A—C14A107.7 (2)
C8B—C9B—C10B—C13B177.4 (2)C2A—C1A—N1A—C14A121.7 (2)
C9A—C10A—C11A—C12A1.0 (4)C7A—C1A—N1A—C5A80.0 (2)
C13A—C10A—C11A—C12A178.2 (3)C2A—C1A—N1A—C5A50.7 (3)
C9B—C10B—C11B—C12B1.5 (4)C18A—C5A—N1A—C14A68.3 (2)
C13B—C10B—C11B—C12B177.9 (3)C4A—C5A—N1A—C14A167.24 (17)
C8A—C7A—C12A—C11A2.0 (4)C18A—C5A—N1A—C1A119.7 (2)
C1A—C7A—C12A—C11A177.9 (2)C4A—C5A—N1A—C1A4.8 (2)
C10A—C11A—C12A—C7A1.0 (5)O2B—C14B—N1B—C1B10.3 (3)
C8B—C7B—C12B—C11B2.3 (4)C15B—C14B—N1B—C1B168.65 (19)
C1B—C7B—C12B—C11B177.8 (2)O2B—C14B—N1B—C5B175.21 (19)
C10B—C11B—C12B—C7B0.7 (4)C15B—C14B—N1B—C5B5.8 (3)
O2A—C14A—C15A—C16A26.0 (3)C7B—C1B—N1B—C14B106.7 (2)
O2A—C14A—C15A—C16A26.0 (3)C2B—C1B—N1B—C14B122.6 (2)
N1A—C14A—C15A—C16A153.0 (2)C7B—C1B—N1B—C5B78.8 (2)
O2A—C14A—C15A—C17A40.4 (3)C2B—C1B—N1B—C5B51.9 (3)
O2A—C14A—C15A—C17A40.4 (3)C18B—C5B—N1B—C14B66.5 (2)
N1A—C14A—C15A—C17A140.5 (2)C4B—C5B—N1B—C14B168.39 (19)
O2B—C14B—C15B—C16B41.4 (3)C18B—C5B—N1B—C1B119.2 (2)
N1B—C14B—C15B—C16B139.6 (2)C4B—C5B—N1B—C1B5.9 (3)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C7A–C12A and C7B–C12B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C23A—H23A···Cg10.932.863.787 (3)173
C23B—H23B···Cg20.932.853.777 (3)173
C5A—H5A···O2Bi0.982.413.366 (3)166
C5B—H5B···O2A0.982.423.381 (3)166
C19A—H19A···O2Bi0.932.593.435 (3)151
Symmetry code: (i) x1, y, z.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg2 are the centroids of the C7A–C12A and C7B–C12B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C23A—H23A···Cg10.932.863.787 (3)173
C23B—H23B···Cg20.932.853.777 (3)173
C5A—H5A···O2Bi0.982.413.366 (3)166
C5B—H5B···O2A0.982.423.381 (3)166
C19A—H19A···O2Bi0.932.593.435 (3)151
Symmetry code: (i) x1, y, z.
 

Acknowledgements

KK thanks the University Grant Commission for the financial support (major research project, F. No. 42–342/2013) of this research work. The authors are grateful to the UGC Networking Resource Centre, University of Hyderabad, for providing characterization facilities and Dr R. Nagarajan, School of Chemistry, University of Hyderabad, for providing laboratory facilities.

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Volume 70| Part 9| September 2014| Pages o1056-o1057
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