Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o832-o833
https://doi.org/10.1107/S2056989015018666

Crystal structure of 2-[4(E)-2,6-bis­­(4-chloro­phen­yl)-3-ethyl­piperidin-4-yl­­idene]acetamide

K. Priya,a K. Saravanan,a S. Selvanayagamb‡ and S. Kabilana*

aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: profskabilan@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 17 September 2015; accepted 5 October 2015; online 10 October 2015)

In the title piperidine derivative, C21H22Cl2N2O, the piperidine ring adopts a chair conformation. The chloro­phenyl rings are oriented at an angle of 45.59 (14)° with respect to each other. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds, forming C(4) chains along [100]. The chains are linked by C—H⋯O hydrogen bonds, forming sheets parallel to the ab plane. Within the sheets, there are N—H⋯π inter­actions present. The crystal studied was refined as an inversion twin.

CCDC reference: 1064003

Similar articles

1. Related literature

For background to piperidienes, their properties and syntheses, see: Deopura et al. (2008[Deopura, L., Gupta, B., Joshi, M. & Alagirusami, R. (2008). Editors. Polyesters and Polyamides. Boca Raton, FL: CRC Press.]); Greenberg et al. (2000[Greenberg, A., Breneman, C. M. & Liebman, F. (2000). Editors. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science. New York: Wiley.]); Johnsson (2004[Johnsson, I. (2004). Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 2, p. 442. New York: Wiley.]); Katritzky et al. (1989[Katritzky, A. R., Pilarski, B. & Urogdi, L. (1989). Synthesis, pp. 949-950.]); Kornblum & Singaram (1979[Kornblum, N. & Singaram, S. (1979). J. Org. Chem. 44, 4727-4729.]); Moorthy & Singhal (2005[Moorthy, J. N. & Singhal, N. (2005). J. Org. Chem. 70, 1926-1929.]); Prostakov & Gaivoronskaya (1978[Prostakov, N. S. & Gaivoronskaya, L. A. (1978). Russ. Chem. Rev. 47, 447-469.]); Yu et al. (2002[Yu, V. K., Nagimova, A. D., Praliev, K. D., Shin, S. N. & Kempe, N. (2002). Pharm. Chem. J. 36, 382-384.]); Zabicky (1970[Zabicky, J. (1970). Editor. The Chemistry of Amides. New York: Wiley.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H22Cl2N2O

  • Mr = 389.30

  • Orthorhombic, P n a 21

  • a = 8.3293 (2) Å

  • b = 12.2924 (3) Å

  • c = 19.3226 (4) Å

  • V = 1978.39 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 296 K

  • 0.22 × 0.20 × 0.18 mm

2.2. Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • 31733 measured reflections

  • 4427 independent reflections

  • 4220 reflections with I > 2σ(I)

  • Rint = 0.022

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.097

  • S = 1.04

  • 4427 reflections

  • 248 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.30 e Å−3

  • Absolute structure: Refined as an inversion twin

  • Absolute structure parameter: 0.37 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2NB⋯O1i 0.82 (1) 2.17 (2) 2.973 (3) 165 (4)
C6—H6⋯O1ii 0.93 2.55 3.454 (3) 163
N1—H1N⋯Cgii 0.82 (1) 2.85 (4) 3.626 (2) 157 (3)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). 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: SHELXL2014/7 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2014/7 and PLATON.

Supporting information

CCDC reference: 1064003

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989015018666/su5218sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015018666/su5218Isup2.hkl

checkCIF report


Chemical context top

The significance of piperidin-4-one as inter­mediates in the synthesis of a range of physiologically active compounds have been reviewed by (Prostakov & Gaivoronskaya, 1978). 4-piperidone derivatives were found to be superior raw materials for preparation of analgesics (Yu et al., 2002). The amide bond is one of the most important functional groups in current chemistry since amides are multipurpose synthetic inter­mediates used in the manufacture of several pharmacological products, polymers, detergents, lubricants, and drug stabilizers, as well as key structural motifs present in numerous natural products (Zabicky, 1970; Greenberg et al., 2000; Deopura et al., 2008; Johnsson, 2004). Usually, amides have been synthesized by the hydration of nitriles, catalyzed by strong acids (Moorthy & Singhal, 2005) and bases (Kornblum & Singaram, 1979; Katritzky et al., 1989). In view of the many inter­esting applications of piperidine derivatives we synthesized the title compound and report herein its crystal structure.

Structural commentary top

The molecular structure of the title compound is illustrated in Fig. 1. The piperidine ring adopts a chair conformation: puckering parameters q2 = 0.007 (3) Å, q3 = -0.609 (3) Å, QT = 0.609 (3) Å, and φ = -175.0 (1)°. Atoms C10 and C7 deviate by 0.724 (3) and -0.714 (3) Å, respectively, from the mean plane through the remaining four atoms. The chlorine atoms, Cl1 and Cl2, deviate by -0.019 (1) and 0.135 (1) Å, respectively, from the chloro­phenyl rings (C1—C6) and (C12—C17) to which they are attached. The two chloro­phenyl rings (C1—C6 and C12—C17) are oriented at a dihedral angle of 45.59 (14)°, and are inclined to the mean plane through the piper­idene ring by 76.32 (13) and 46.27 (12) °, respectively.

Supra­molecular features top

In the crystal, moleculesare linked via N—H···O hydrogen bonds into C(4) chains propagating along [100] (Table 1 and Fig. 2). The chains are linked by C—H···O hydrogen bonds forming sheets parallel to the ab plane (Table 1 and Fig. 2). Within the sheets there are N—H···π inter­actions present (see Table 1 and Fig. 3).

Synthesis and crystallization top

The title (2,6-di­aryl­piperidin-4-yl­idene)aceto­nitrile was refluxed with a few drops of diluted Sulphuric acid for 30-45 mins. After completion of the reaction (monitored by TLC) the mixture was neutralized with saturated sodiumbicarbonate solution, until the disappearance of brisk effervescence. After the solid that appeared was filtered and dried. This crude product mass was purified by column-chromatography over silica-gel (100–200 mesh) using petroleum ether and ethyl­acetate (25%) as eluent to give the title compound. Suitable colourless block-like crystals were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Atoms H1N, H2NA and H2NB were located from a difference Fourier map and freely refined. The remaining H atoms were positioned geometrically and treated as riding on their parent C atoms: C—H = 0.93-0.98 Å with Uiso(H) = 1.5Ueq (C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

Related literature top

For background to piperidienes, their properties and syntheses, see: Deopura et al. (2008); Greenberg et al. (2000); Johnsson (2004); Katritzky et al. (1989); Kornblum & Singaram (1979); Moorthy & Singhal (2005); Prostakov & Gaivoronskaya (1978); Yu et al. (2002); Zabicky (1970).

Structure description top

The significance of piperidin-4-one as inter­mediates in the synthesis of a range of physiologically active compounds have been reviewed by (Prostakov & Gaivoronskaya, 1978). 4-piperidone derivatives were found to be superior raw materials for preparation of analgesics (Yu et al., 2002). The amide bond is one of the most important functional groups in current chemistry since amides are multipurpose synthetic inter­mediates used in the manufacture of several pharmacological products, polymers, detergents, lubricants, and drug stabilizers, as well as key structural motifs present in numerous natural products (Zabicky, 1970; Greenberg et al., 2000; Deopura et al., 2008; Johnsson, 2004). Usually, amides have been synthesized by the hydration of nitriles, catalyzed by strong acids (Moorthy & Singhal, 2005) and bases (Kornblum & Singaram, 1979; Katritzky et al., 1989). In view of the many inter­esting applications of piperidine derivatives we synthesized the title compound and report herein its crystal structure.

The molecular structure of the title compound is illustrated in Fig. 1. The piperidine ring adopts a chair conformation: puckering parameters q2 = 0.007 (3) Å, q3 = -0.609 (3) Å, QT = 0.609 (3) Å, and φ = -175.0 (1)°. Atoms C10 and C7 deviate by 0.724 (3) and -0.714 (3) Å, respectively, from the mean plane through the remaining four atoms. The chlorine atoms, Cl1 and Cl2, deviate by -0.019 (1) and 0.135 (1) Å, respectively, from the chloro­phenyl rings (C1—C6) and (C12—C17) to which they are attached. The two chloro­phenyl rings (C1—C6 and C12—C17) are oriented at a dihedral angle of 45.59 (14)°, and are inclined to the mean plane through the piper­idene ring by 76.32 (13) and 46.27 (12) °, respectively.

In the crystal, moleculesare linked via N—H···O hydrogen bonds into C(4) chains propagating along [100] (Table 1 and Fig. 2). The chains are linked by C—H···O hydrogen bonds forming sheets parallel to the ab plane (Table 1 and Fig. 2). Within the sheets there are N—H···π inter­actions present (see Table 1 and Fig. 3).

For background to piperidienes, their properties and syntheses, see: Deopura et al. (2008); Greenberg et al. (2000); Johnsson (2004); Katritzky et al. (1989); Kornblum & Singaram (1979); Moorthy & Singhal (2005); Prostakov & Gaivoronskaya (1978); Yu et al. (2002); Zabicky (1970).

Synthesis and crystallization top

The title (2,6-di­aryl­piperidin-4-yl­idene)aceto­nitrile was refluxed with a few drops of diluted Sulphuric acid for 30-45 mins. After completion of the reaction (monitored by TLC) the mixture was neutralized with saturated sodiumbicarbonate solution, until the disappearance of brisk effervescence. After the solid that appeared was filtered and dried. This crude product mass was purified by column-chromatography over silica-gel (100–200 mesh) using petroleum ether and ethyl­acetate (25%) as eluent to give the title compound. Suitable colourless block-like crystals were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. Atoms H1N, H2NA and H2NB were located from a difference Fourier map and freely refined. The remaining H atoms were positioned geometrically and treated as riding on their parent C atoms: C—H = 0.93-0.98 Å with Uiso(H) = 1.5Ueq (C) for methyl H atoms and 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound, viewed along the c axis. The N—H···O and C-H···O hydrogen bonds are shown as dashed lines (see Table 1). For clarity H atoms not involved in these hydrogen bonds have been omitted.
[Figure 3] Fig. 3. Crystal packing of the title compound, showing the N—H···π interactions as dashed lines (see Table 1). For clarity H atoms not involved in these interactions have been omitted.
2-[4(E)-2,6-Bis(4-chlorophenyl)-3-ethylpiperidin-4-ylidene]acetamide top
Crystal data top
C21H22Cl2N2ODx = 1.307 Mg m−3
Mr = 389.30Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 24148 reflections
a = 8.3293 (2) Åθ = 2.2–27.4°
b = 12.2924 (3) ŵ = 0.34 mm−1
c = 19.3226 (4) ÅT = 296 K
V = 1978.39 (8) Å3Block, colourless
Z = 40.22 × 0.20 × 0.18 mm
F(000) = 816
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		Rint = 0.022
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.0°
ω scansh = −10→10
31733 measured reflectionsk = −15→15
4427 independent reflectionsl = −25→23
4220 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.4463P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4427 reflectionsΔρmax = 0.40 e Å−3
248 parametersΔρmin = −0.30 e Å−3
4 restraintsAbsolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.37 (7)
Crystal data top
C21H22Cl2N2OV = 1978.39 (8) Å3
Mr = 389.30Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 8.3293 (2) ŵ = 0.34 mm−1
b = 12.2924 (3) ÅT = 296 K
c = 19.3226 (4) Å0.22 × 0.20 × 0.18 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		4220 reflections with I > 2σ(I)
31733 measured reflectionsRint = 0.022
4427 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097Δρmax = 0.40 e Å−3
S = 1.04Δρmin = −0.30 e Å−3
4427 reflectionsAbsolute structure: Refined as an inversion twin
248 parametersAbsolute structure parameter: 0.37 (7)
4 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.04419 (14)0.50344 (7)0.45059 (5)0.0738 (3)
Cl20.93853 (17)0.89463 (11)−0.00442 (7)0.1046 (5)
O1−0.1377 (2)1.14174 (17)0.30563 (13)0.0563 (5)
N10.3564 (2)0.88167 (15)0.23773 (11)0.0350 (4)
N20.0334 (3)1.2760 (2)0.33460 (15)0.0547 (6)
C10.1001 (3)0.6176 (2)0.40293 (14)0.0424 (6)
C20.0568 (4)0.7187 (2)0.42740 (14)0.0464 (6)
H2−0.00330.72540.46770.056*
C30.1046 (3)0.8104 (2)0.39085 (14)0.0432 (5)
H30.07990.87910.40800.052*
C40.1888 (3)0.80111 (17)0.32911 (12)0.0323 (4)
C50.2270 (3)0.69817 (19)0.30503 (13)0.0358 (5)
H50.28180.69070.26340.043*
C60.1841 (3)0.60526 (19)0.34250 (14)0.0402 (5)
H60.21220.53640.32670.048*
C70.2364 (3)0.90357 (17)0.29068 (12)0.0332 (5)
H70.28240.95490.32410.040*
C80.0906 (3)0.95793 (18)0.25622 (14)0.0361 (5)
H8A0.04330.90930.22240.043*
H8B0.00990.97510.29070.043*
C90.1484 (2)1.06071 (18)0.22138 (13)0.0336 (5)
C100.2759 (2)1.03897 (18)0.16737 (12)0.0328 (4)
H100.23080.98710.13410.039*
C110.4174 (2)0.98078 (18)0.20494 (13)0.0326 (4)
H110.45971.02920.24090.039*
C120.5523 (2)0.95166 (19)0.15563 (13)0.0346 (5)
C130.6907 (3)1.0149 (2)0.15428 (18)0.0477 (6)
H130.70321.07070.18640.057*
C140.8102 (3)0.9962 (3)0.1058 (2)0.0583 (8)
H140.90141.03980.10470.070*
C150.7925 (4)0.9128 (3)0.05980 (18)0.0587 (8)
C160.6613 (4)0.8458 (3)0.06195 (18)0.0600 (8)
H160.65300.78740.03150.072*
C170.5407 (3)0.8655 (2)0.10996 (16)0.0470 (6)
H170.45120.82040.11140.056*
C180.3314 (3)1.1388 (2)0.12639 (14)0.0401 (5)
H18A0.36251.19550.15860.048*
H18B0.42551.11940.09950.048*
C190.2027 (4)1.1833 (2)0.07772 (17)0.0519 (7)
H19A0.24401.24550.05350.078*
H19B0.17311.12820.04490.078*
H19C0.11001.20430.10410.078*
C200.1091 (3)1.16038 (19)0.24254 (13)0.0368 (5)
H200.16101.21800.22080.044*
C21−0.0092 (3)1.18930 (19)0.29731 (14)0.0393 (5)
H1N0.430 (3)0.850 (3)0.2575 (17)0.050 (9)*
H2NA−0.032 (3)1.298 (3)0.3633 (15)0.047 (9)*
H2NB0.125 (2)1.301 (3)0.334 (2)0.066 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1153 (8)0.0524 (4)0.0536 (4)−0.0239 (4)0.0060 (5)0.0144 (3)
Cl20.1058 (8)0.1019 (8)0.1062 (9)0.0398 (7)0.0651 (8)0.0203 (7)
O10.0416 (10)0.0438 (10)0.0835 (16)0.0000 (8)0.0188 (10)−0.0017 (10)
N10.0271 (9)0.0326 (9)0.0453 (11)0.0044 (7)−0.0004 (8)0.0075 (8)
N20.0546 (14)0.0479 (13)0.0615 (16)−0.0027 (11)0.0157 (13)−0.0105 (12)
C10.0502 (14)0.0401 (12)0.0370 (13)−0.0066 (10)−0.0053 (11)0.0088 (10)
C20.0533 (14)0.0520 (15)0.0339 (12)0.0017 (12)0.0073 (11)0.0025 (10)
C30.0492 (14)0.0391 (12)0.0413 (13)0.0082 (10)0.0035 (11)−0.0012 (10)
C40.0303 (9)0.0321 (10)0.0345 (11)0.0019 (8)−0.0046 (9)0.0032 (8)
C50.0326 (10)0.0372 (11)0.0375 (12)−0.0005 (9)0.0011 (9)−0.0016 (9)
C60.0454 (13)0.0317 (11)0.0436 (13)−0.0005 (9)−0.0047 (11)−0.0017 (9)
C70.0315 (10)0.0293 (10)0.0387 (12)−0.0006 (8)−0.0021 (9)0.0009 (8)
C80.0265 (9)0.0305 (10)0.0514 (14)0.0017 (8)0.0029 (9)0.0078 (9)
C90.0247 (9)0.0319 (10)0.0443 (12)0.0013 (8)−0.0018 (9)0.0068 (9)
C100.0271 (9)0.0308 (9)0.0406 (12)0.0001 (8)−0.0003 (8)0.0019 (9)
C110.0254 (9)0.0326 (10)0.0399 (12)−0.0016 (8)−0.0016 (8)−0.0008 (9)
C120.0280 (9)0.0342 (10)0.0416 (12)0.0036 (8)−0.0007 (9)0.0041 (9)
C130.0318 (11)0.0512 (14)0.0602 (16)−0.0026 (10)0.0024 (12)−0.0017 (13)
C140.0344 (13)0.0653 (19)0.075 (2)0.0031 (12)0.0135 (13)0.0118 (16)
C150.0528 (16)0.0614 (18)0.0619 (18)0.0242 (14)0.0213 (14)0.0157 (14)
C160.079 (2)0.0479 (15)0.0534 (17)0.0151 (15)0.0114 (16)−0.0061 (12)
C170.0484 (14)0.0404 (12)0.0522 (16)0.0003 (11)0.0026 (12)−0.0026 (11)
C180.0355 (11)0.0383 (11)0.0465 (14)0.0017 (9)0.0071 (10)0.0073 (10)
C190.0494 (15)0.0527 (15)0.0537 (16)0.0108 (12)0.0062 (13)0.0176 (13)
C200.0338 (10)0.0308 (10)0.0457 (13)0.0001 (8)0.0032 (10)0.0057 (9)
C210.0387 (12)0.0299 (11)0.0494 (14)0.0060 (9)0.0053 (10)0.0065 (9)
Geometric parameters (Å, º) top
Cl1—C11.742 (3)C9—C201.332 (3)
Cl2—C151.752 (3)C9—C101.513 (3)
O1—C211.230 (3)C10—C181.531 (3)
N1—C71.455 (3)C10—C111.558 (3)
N1—C111.464 (3)C10—H100.9800
N1—H1N0.821 (14)C11—C121.516 (3)
N2—C211.334 (4)C11—H110.9800
N2—H2NA0.824 (14)C12—C171.381 (4)
N2—H2NB0.824 (14)C12—C131.390 (3)
C1—C61.370 (4)C13—C141.386 (4)
C1—C21.378 (4)C13—H130.9300
C2—C31.389 (4)C14—C151.365 (5)
C2—H20.9300C14—H140.9300
C3—C41.388 (4)C15—C161.370 (5)
C3—H30.9300C16—C171.389 (4)
C4—C51.385 (3)C16—H160.9300
C4—C71.515 (3)C17—H170.9300
C5—C61.399 (3)C18—C191.528 (4)
C5—H50.9300C18—H18A0.9700
C6—H60.9300C18—H18B0.9700
C7—C81.538 (3)C19—H19A0.9600
C7—H70.9800C19—H19B0.9600
C8—C91.510 (3)C19—H19C0.9600
C8—H8A0.9700C20—C211.489 (4)
C8—H8B0.9700C20—H200.9300
C7—N1—C11112.88 (17)C11—C10—H10107.3
C7—N1—H1N106 (3)N1—C11—C12109.44 (18)
C11—N1—H1N110 (2)N1—C11—C10108.71 (17)
C21—N2—H2NA117 (2)C12—C11—C10112.1 (2)
C21—N2—H2NB123 (3)N1—C11—H11108.8
H2NA—N2—H2NB120 (4)C12—C11—H11108.8
C6—C1—C2121.7 (2)C10—C11—H11108.8
C6—C1—Cl1119.9 (2)C17—C12—C13118.3 (2)
C2—C1—Cl1118.4 (2)C17—C12—C11122.1 (2)
C1—C2—C3118.9 (2)C13—C12—C11119.6 (2)
C1—C2—H2120.6C14—C13—C12121.0 (3)
C3—C2—H2120.6C14—C13—H13119.5
C4—C3—C2121.0 (2)C12—C13—H13119.5
C4—C3—H3119.5C15—C14—C13119.1 (3)
C2—C3—H3119.5C15—C14—H14120.4
C5—C4—C3118.7 (2)C13—C14—H14120.4
C5—C4—C7122.3 (2)C14—C15—C16121.2 (3)
C3—C4—C7119.0 (2)C14—C15—Cl2118.8 (3)
C4—C5—C6120.9 (2)C16—C15—Cl2119.9 (3)
C4—C5—H5119.6C15—C16—C17119.5 (3)
C6—C5—H5119.6C15—C16—H16120.3
C1—C6—C5118.8 (2)C17—C16—H16120.3
C1—C6—H6120.6C12—C17—C16120.7 (3)
C5—C6—H6120.6C12—C17—H17119.7
N1—C7—C4111.75 (18)C16—C17—H17119.7
N1—C7—C8108.56 (19)C19—C18—C10113.2 (2)
C4—C7—C8111.50 (18)C19—C18—H18A108.9
N1—C7—H7108.3C10—C18—H18A108.9
C4—C7—H7108.3C19—C18—H18B108.9
C8—C7—H7108.3C10—C18—H18B108.9
C9—C8—C7107.72 (18)H18A—C18—H18B107.8
C9—C8—H8A110.2C18—C19—H19A109.5
C7—C8—H8A110.2C18—C19—H19B109.5
C9—C8—H8B110.2H19A—C19—H19B109.5
C7—C8—H8B110.2C18—C19—H19C109.5
H8A—C8—H8B108.5H19A—C19—H19C109.5
C20—C9—C8123.6 (2)H19B—C19—H19C109.5
C20—C9—C10123.1 (2)C9—C20—C21126.9 (2)
C8—C9—C10112.56 (19)C9—C20—H20116.6
C9—C10—C18115.28 (18)C21—C20—H20116.6
C9—C10—C11106.90 (18)O1—C21—N2122.7 (3)
C18—C10—C11112.36 (18)O1—C21—C20123.7 (2)
C9—C10—H10107.3N2—C21—C20113.5 (2)
C18—C10—H10107.3
C6—C1—C2—C3−2.2 (4)C7—N1—C11—C10−62.6 (2)
Cl1—C1—C2—C3178.2 (2)C9—C10—C11—N157.4 (2)
C1—C2—C3—C42.7 (4)C18—C10—C11—N1−175.2 (2)
C2—C3—C4—C5−1.1 (4)C9—C10—C11—C12178.48 (18)
C2—C3—C4—C7179.2 (2)C18—C10—C11—C12−54.1 (3)
C3—C4—C5—C6−1.0 (3)N1—C11—C12—C1745.3 (3)
C7—C4—C5—C6178.6 (2)C10—C11—C12—C17−75.4 (3)
C2—C1—C6—C50.1 (4)N1—C11—C12—C13−136.7 (2)
Cl1—C1—C6—C5179.7 (2)C10—C11—C12—C13102.6 (3)
C4—C5—C6—C11.5 (4)C17—C12—C13—C143.6 (4)
C11—N1—C7—C4−173.73 (18)C11—C12—C13—C14−174.5 (3)
C11—N1—C7—C862.9 (2)C12—C13—C14—C15−1.3 (5)
C5—C4—C7—N1−14.2 (3)C13—C14—C15—C16−1.9 (5)
C3—C4—C7—N1165.5 (2)C13—C14—C15—Cl2176.3 (2)
C5—C4—C7—C8107.5 (3)C14—C15—C16—C172.7 (5)
C3—C4—C7—C8−72.8 (3)Cl2—C15—C16—C17−175.5 (2)
N1—C7—C8—C9−58.3 (2)C13—C12—C17—C16−2.8 (4)
C4—C7—C8—C9178.2 (2)C11—C12—C17—C16175.2 (3)
C7—C8—C9—C20−111.6 (2)C15—C16—C17—C12−0.3 (5)
C7—C8—C9—C1059.3 (3)C9—C10—C18—C19−68.9 (3)
C20—C9—C10—C18−13.2 (3)C11—C10—C18—C19168.3 (2)
C8—C9—C10—C18175.8 (2)C8—C9—C20—C21−7.2 (4)
C20—C9—C10—C11112.5 (2)C10—C9—C20—C21−177.2 (2)
C8—C9—C10—C11−58.5 (2)C9—C20—C21—O1−39.1 (4)
C7—N1—C11—C12174.66 (19)C9—C20—C21—N2144.3 (3)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2NB···O1i0.82 (1)2.17 (2)2.973 (3)165 (4)
C6—H6···O1ii0.932.553.454 (3)163
N1—H1N···Cgii0.82 (1)2.85 (4)3.626 (2)157 (3)
Symmetry codes: (i) x+1/2, −y+5/2, z; (ii) x+1/2, −y+3/2, z.
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2NB···O1i0.82 (1)2.17 (2)2.973 (3)165 (4)
C6—H6···O1ii0.932.553.454 (3)163
N1—H1N···Cgii0.82 (1)2.85 (4)3.626 (2)157 (3)
Symmetry codes: (i) x+1/2, −y+5/2, z; (ii) x+1/2, −y+3/2, z.
 

Footnotes

‡Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.

Acknowledgements

KP is thankful to the UGC, New Delhi for the award of a UGC–BSR-RFSMS Fellowship. The authors would also like thank to the Department of Biotechnology (DBT & NEC), New Delhi, for financial support.

References

First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDeopura, L., Gupta, B., Joshi, M. & Alagirusami, R. (2008). Editors. Polyesters and Polyamides. Boca Raton, FL: CRC Press.  Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationGreenberg, A., Breneman, C. M. & Liebman, F. (2000). Editors. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science. New York: Wiley.  Google Scholar
 First citationJohnsson, I. (2004). Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 2, p. 442. New York: Wiley.  Google Scholar
 First citationKatritzky, A. R., Pilarski, B. & Urogdi, L. (1989). Synthesis, pp. 949–950.  CrossRef Google Scholar
 First citationKornblum, N. & Singaram, S. (1979). J. Org. Chem. 44, 4727–4729.  CrossRef CAS Web of Science Google Scholar
 First citationMoorthy, J. N. & Singhal, N. (2005). J. Org. Chem. 70, 1926–1929.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationProstakov, N. S. & Gaivoronskaya, L. A. (1978). Russ. Chem. Rev. 47, 447–469.  CrossRef Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationYu, V. K., Nagimova, A. D., Praliev, K. D., Shin, S. N. & Kempe, N. (2002). Pharm. Chem. J. 36, 382–384.  CrossRef CAS Google Scholar
 First citationZabicky, J. (1970). Editor. The Chemistry of Amides. New York: Wiley.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 11| November 2015| Pages o832-o833
https://doi.org/10.1107/S2056989015018666
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS