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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 9| September 2015| Pages o663-o664
https://doi.org/10.1107/S2056989015014887

Crystal structure of 5-benzoyl-2,4-di­phenyl-4,5-di­hydro­furan-3-carbo­nitrile

CROSSMARK_Color_square_no_text.svg
V. Rajni Swamy,a R.V. Krishnakumar,a* S. Sivakumar,b N. Srinivasana and R. Ranjith Kumarb

aDepartment of Physics, Thiagarajar College, Madurai 625 009, Tamil Nadu, India, and bSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, Tamil Nadu, India
*Correspondence e-mail: mailtorvkk@yahoo.co.in

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 31 July 2015; accepted 8 August 2015; online 15 August 2015)

In the title compound, C24H17NO2, the carbonyl O atom of the benzoyl group is cis with respect to the furanyl O atom, and the associated O—C—C—O torsion angle is 4.62 (19)°. The puckering of the dihydro­furan ring is close to twisted (4T5), with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. Mol­ecules are inter­connected via a C—H⋯N and a C—H⋯O hydrogen bond, leading to layers parallel to the (200) plane and characterized by R44(28) and R44(36) graph-set motifs. The furan O atom does not participate in inter­molecular hydrogen bonding. The crystal lattice encompasses a solvent-accessible void of 24.7 (8) Å3.

CCDC reference: 1023392

Similar articles

1. Related literature

For biological activity of di­hydro­furans, see: Simmonds et al. (1990[Simmonds, M. S. J., Blaney, W. M., Ley, S. V., Anderson, J. C. & Toogood, P. L. (1990). Entomol. Exp. Appl. 55, 169-181.]); Gebbinck et al. (1999[Gebbinck, E. A. K., Stork, G. A., Jansen, B. J. M. & de Groot, A. (1999). Tetrahedron, 55, 11077-11094.]); Ley et al. (1987[Ley, S. V., Santafianos, D., Blaney, W. M. & Simmonds, M. S. J. (1987). Tetrahedron Lett. 28, 221-224.]); Kumar et al. (2003[Kumar, V. T., Rao, S. K., Narayana, L. V., Dubey, P. K. & Aparna, V. (2003). Heterocycl. Commun. 9, 51-56.]); Pour et al. (2003[Pour, M., Špulák, M., Balšánek, V., Kuneš, J., Kubanová, P. & Buchta, V. (2003). Bioorg. Med. Chem. 11, 2843-2866.]); Loğoğlu et al. (2010[Loğoğlu, E., Yilmaz, M., Katircioğlu, H., Yakut, M. & Mercan, S. (2010). Med. Chem. Res. 19, 490-497.]). For Cambridge Structural Database, see: Groom & Allen (2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering of rings, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For related structures, see: Rajni Swamy et al. (2012[Rajni Swamy, V., Krishnakumar, R. V., Srinivasan, N., Gunasekaran, P. & Perumal, S. (2012). Acta Cryst. E68, o3441.]); Suresh et al. (2012a[Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012a). Acta Cryst. E68, o2397.],b[Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012b). Acta Cryst. E68, o1124.],c[Suresh, J., Vishnupriya, R., Gunasekaran, P., Perumal, S. & Lakshman, P. L. N. (2012c). Acta Cryst. E68, o1576.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C24H17NO2

  • Mr = 351.38

  • Monoclinic, P 21 /n

  • a = 10.0704 (7) Å

  • b = 15.7994 (12) Å

  • c = 11.8632 (9) Å

  • β = 98.886 (3)°

  • V = 1864.9 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 K

  • 0.35 × 0.24 × 0.08 mm

2.2. Data collection

  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.994

  • 34345 measured reflections

  • 4648 independent reflections

  • 2305 reflections with I > 2σ(I)

  • Rint = 0.063

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.147

  • S = 0.99

  • 4648 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11⋯N1i 0.93 2.63 3.487 (2) 154
C21—H21⋯O2ii 0.93 2.58 3.277 (2) 132
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1023392

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989015014887/xu5865sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015014887/xu5865Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015014887/xu5865Isup3.cml

checkCIF report


Introduction top

The title compound 5-benzoyl-2,4-di­phenyl-4,5-di­hydro­furan-3-carbo­nitrile (I) is a di­hydro­furan carbo­nitrile derivative. Di­hydro­furans belong to an important class of heterocycles and are known for distinct insect anti­feedant activities (Gebbinck et al., 1999). Di­hydro­furans have also been found to possess anti­fungal (Pour et al., 2003) and anti-inflammatory properties (Kumar et al., 2003). The di­hydro­furan derivatives with their reactive functional groups like meth­oxy, carbonyl etc. may prove to be promising candidates for the synthesis of novel heterocyclic compounds. The in vitro anti­bacterial and anti­fungal activities of some furan derivatives, specifically, 4,5-di­hydro­furan-3-carbo­nitriles were investigated against some bacteria and fungi and were found to show activity against bacteria better than some known anti­biotics (Loğoğlu et al., 2010).

Experimental top

Synthesis and crystallization top

A mixture of benzoyl­aceto­nitrile (1.0 mmol), benzaldehyde (1.0 mmol) and imidazolium salt (1-methyl-3-(2-oxo-2-phenyl­ethyl)-1H-imidazol-3-ium bromide) (1.0 mmol) were dissolved in EtOH (10 mL) then Et3N(tri­ethyl­amine) (1.0 mmol) was added slowly and refluxed on a water bath. The consumption of starting material was monitored by TLC. After 3hours the reaction mixture was cooled and the precipitated solid product was filtered and washed. Crystals of (1) suitable for diffraction were obtained.

Refinement top

All H atoms were included into the model at geometrically calculated positions (C—H target distance = 0.98 Å for methine H atoms and 0.93 Å for all other aromatic H atoms) and refined using a riding model. The Uiso values of all H atoms were constrained to 1.2 times Ueq of the respective atom to which the H atom binds.

Results and discussion top

The carbonyl O of the benzoyl group is cis with the furanyl O atom with the value of the associated torsion angle being 4.62°. The puckering of the hydro­furan ring is close to twisted (4T5) with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. The angle between the mean plane about the furan ring atoms and the 2-phenyl ring is 22.5 (1)° while those with respect to the 4-phenyl and the 5-benzoyl group atoms are 88.6 (1) and 78.4 (1)°, respectively.

A search in the CSD [version 5.53, update 3, May 2013] for organic nonpolymeric single crystal structures for which 3D coordinates determined with no disorder, no ions and no other errors with R-factors less than 0.05 revealed 6287 structures of which 2498 had the furan O involved in C—H···O inter­actions with the H···A ranging from 2.127 to 2.720 Å. Also, four structures bearing close relationships to the title compound with refcodes LEFJUD (Suresh et al., 2012a), YAXGOV (Suresh et al., 2012b), ZARBEB (Suresh et al., 2012c) and EDUZAG (Rajni Rajni et al., 2012) were found. These structures differ by an indole ring replaced by a phenyl in the title compound and inter­estingly none display any change in the crystal system or lattice type. However, there are drastic differences in the inter­molecular inter­action patterns. The molecules are inter­connected via a C—H···N and a C—H···O hydrogen-bond leading to a layers parallel to the (200) plane and characterized by R44(28) and R44(36) graph-set motifs. The furan O atom does not participate in the inter­molecular hydrogen bonding. The crystal lattice encompasses a solvent accessible void of 24.7 (8) Å3.

Related literature top

For biological activity of dihydrofurans, see: Simmonds et al. (1990); Gebbinck et al. (1999); Ley et al. (1987); Kumar et al. (2003); Pour et al. (2003); Loğoğlu et al. (2010). For Cambridge Structural Database, see: Groom & Allen (2014). For graph-set motifs, see: Bernstein et al. (1995). For puckering of rings, see: Cremer & Pople (1975). For related structures, see: Rajni Swamy et al. (2012); Suresh et al. (2012a,b,c).

Structure description top

The title compound 5-benzoyl-2,4-di­phenyl-4,5-di­hydro­furan-3-carbo­nitrile (I) is a di­hydro­furan carbo­nitrile derivative. Di­hydro­furans belong to an important class of heterocycles and are known for distinct insect anti­feedant activities (Gebbinck et al., 1999). Di­hydro­furans have also been found to possess anti­fungal (Pour et al., 2003) and anti-inflammatory properties (Kumar et al., 2003). The di­hydro­furan derivatives with their reactive functional groups like meth­oxy, carbonyl etc. may prove to be promising candidates for the synthesis of novel heterocyclic compounds. The in vitro anti­bacterial and anti­fungal activities of some furan derivatives, specifically, 4,5-di­hydro­furan-3-carbo­nitriles were investigated against some bacteria and fungi and were found to show activity against bacteria better than some known anti­biotics (Loğoğlu et al., 2010).

The carbonyl O of the benzoyl group is cis with the furanyl O atom with the value of the associated torsion angle being 4.62°. The puckering of the hydro­furan ring is close to twisted (4T5) with parameters Q = 0.1856 (16) Å and φ = 313.5 (5)°. The angle between the mean plane about the furan ring atoms and the 2-phenyl ring is 22.5 (1)° while those with respect to the 4-phenyl and the 5-benzoyl group atoms are 88.6 (1) and 78.4 (1)°, respectively.

A search in the CSD [version 5.53, update 3, May 2013] for organic nonpolymeric single crystal structures for which 3D coordinates determined with no disorder, no ions and no other errors with R-factors less than 0.05 revealed 6287 structures of which 2498 had the furan O involved in C—H···O inter­actions with the H···A ranging from 2.127 to 2.720 Å. Also, four structures bearing close relationships to the title compound with refcodes LEFJUD (Suresh et al., 2012a), YAXGOV (Suresh et al., 2012b), ZARBEB (Suresh et al., 2012c) and EDUZAG (Rajni Rajni et al., 2012) were found. These structures differ by an indole ring replaced by a phenyl in the title compound and inter­estingly none display any change in the crystal system or lattice type. However, there are drastic differences in the inter­molecular inter­action patterns. The molecules are inter­connected via a C—H···N and a C—H···O hydrogen-bond leading to a layers parallel to the (200) plane and characterized by R44(28) and R44(36) graph-set motifs. The furan O atom does not participate in the inter­molecular hydrogen bonding. The crystal lattice encompasses a solvent accessible void of 24.7 (8) Å3.

For biological activity of dihydrofurans, see: Simmonds et al. (1990); Gebbinck et al. (1999); Ley et al. (1987); Kumar et al. (2003); Pour et al. (2003); Loğoğlu et al. (2010). For Cambridge Structural Database, see: Groom & Allen (2014). For graph-set motifs, see: Bernstein et al. (1995). For puckering of rings, see: Cremer & Pople (1975). For related structures, see: Rajni Swamy et al. (2012); Suresh et al. (2012a,b,c).

Synthesis and crystallization top

A mixture of benzoyl­aceto­nitrile (1.0 mmol), benzaldehyde (1.0 mmol) and imidazolium salt (1-methyl-3-(2-oxo-2-phenyl­ethyl)-1H-imidazol-3-ium bromide) (1.0 mmol) were dissolved in EtOH (10 mL) then Et3N(tri­ethyl­amine) (1.0 mmol) was added slowly and refluxed on a water bath. The consumption of starting material was monitored by TLC. After 3hours the reaction mixture was cooled and the precipitated solid product was filtered and washed. Crystals of (1) suitable for diffraction were obtained.

Refinement details top

All H atoms were included into the model at geometrically calculated positions (C—H target distance = 0.98 Å for methine H atoms and 0.93 Å for all other aromatic H atoms) and refined using a riding model. The Uiso values of all H atoms were constrained to 1.2 times Ueq of the respective atom to which the H atom binds.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view down the b axis, showing molecules interconnected via C—H···N and a C—H···O hydrogen bonds, leading to layers parallel to the (200) plane.
[Figure 3] Fig. 3. A view of the molecules of the unit cell, showing C—H···N and C—H···O hydrogen bonds.
5-Benzoyl-2,4-diphenyl-4,5-dihydrofuran-3-carbonitrile top
Crystal data top
C24H17NO2F(000) = 736
Mr = 351.38Dx = 1.252 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.0704 (7) ÅCell parameters from 2305 reflections
b = 15.7994 (12) Åθ = 2.2–28.6°
c = 11.8632 (9) ŵ = 0.08 mm−1
β = 98.886 (3)°T = 298 K
V = 1864.9 (2) Å3Block, colourless
Z = 40.35 × 0.24 × 0.08 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer		2305 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
ω and φ scansθmax = 28.6°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −13→12
Tmin = 0.973, Tmax = 0.994k = −21→21
34345 measured reflectionsl = −15→15
4648 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0717P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.15 e Å−3
4648 reflectionsΔρmin = −0.16 e Å−3
245 parametersExtinction correction: SHELXL2014 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0097 (17)
Crystal data top
C24H17NO2V = 1864.9 (2) Å3
Mr = 351.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0704 (7) ŵ = 0.08 mm−1
b = 15.7994 (12) ÅT = 298 K
c = 11.8632 (9) Å0.35 × 0.24 × 0.08 mm
β = 98.886 (3)°
Data collection top
Bruker SMART APEXII CCD
diffractometer		4648 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2305 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.994Rint = 0.063
34345 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 0.99Δρmax = 0.15 e Å−3
4648 reflectionsΔρmin = −0.16 e Å−3
245 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.65312 (11)0.12681 (7)−0.07149 (10)0.0503 (3)
O20.63839 (11)0.02849 (7)0.10317 (10)0.0584 (4)
N10.84295 (18)0.37076 (11)0.11942 (17)0.0817 (6)
C10.74999 (16)0.18513 (10)−0.03978 (14)0.0430 (4)
C20.70930 (15)0.24665 (10)0.02407 (13)0.0423 (4)
C30.56268 (15)0.23450 (9)0.03502 (13)0.0416 (4)
H30.55150.23650.11560.050*
C40.54406 (15)0.14312 (9)−0.00964 (14)0.0432 (4)
H40.45860.1385−0.06140.052*
C50.54745 (15)0.07881 (10)0.08555 (14)0.0425 (4)
C60.43803 (15)0.08113 (10)0.15584 (14)0.0436 (4)
C70.32474 (17)0.13099 (11)0.12818 (16)0.0529 (5)
H70.31580.16510.06350.063*
C80.22520 (18)0.13050 (12)0.19565 (18)0.0639 (5)
H80.14870.16350.17590.077*
C90.23861 (19)0.08169 (13)0.29133 (18)0.0673 (6)
H90.17200.08210.33760.081*
C100.3498 (2)0.03227 (13)0.31933 (18)0.0690 (6)
H100.3584−0.00110.38460.083*
C110.44916 (18)0.03135 (11)0.25209 (16)0.0557 (5)
H110.5242−0.00300.27160.067*
C120.87832 (16)0.16935 (11)−0.07951 (14)0.0466 (4)
C130.9140 (2)0.08775 (12)−0.10240 (16)0.0633 (5)
H130.85580.0433−0.09410.076*
C141.0350 (2)0.07193 (15)−0.13726 (19)0.0773 (6)
H141.05910.0165−0.15130.093*
C151.12049 (19)0.13654 (15)−0.15166 (17)0.0702 (6)
H151.20210.1253−0.17600.084*
C161.08594 (19)0.21745 (15)−0.13026 (17)0.0691 (6)
H161.14410.2616−0.14020.083*
C170.96536 (17)0.23435 (12)−0.09402 (16)0.0594 (5)
H170.94250.2898−0.07930.071*
C180.47459 (14)0.29991 (9)−0.03105 (13)0.0414 (4)
C190.44746 (16)0.29744 (10)−0.14855 (15)0.0488 (4)
H190.47970.2527−0.18760.059*
C200.37323 (16)0.36044 (11)−0.20860 (16)0.0565 (5)
H200.35510.3577−0.28780.068*
C210.32609 (18)0.42665 (12)−0.15322 (19)0.0635 (5)
H210.27630.4692−0.19420.076*
C220.3523 (2)0.43001 (12)−0.03784 (19)0.0745 (6)
H220.32070.47540.00030.089*
C230.42525 (19)0.36704 (11)0.02362 (17)0.0646 (5)
H230.44130.36990.10290.078*
C240.78533 (16)0.31484 (11)0.07499 (16)0.0513 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0546 (7)0.0452 (7)0.0539 (7)−0.0099 (6)0.0172 (6)−0.0127 (5)
O20.0528 (7)0.0550 (8)0.0674 (9)0.0109 (6)0.0097 (6)0.0034 (6)
N10.0806 (12)0.0659 (11)0.0966 (14)−0.0206 (10)0.0077 (10)−0.0269 (10)
C10.0468 (9)0.0375 (9)0.0443 (10)−0.0054 (8)0.0060 (8)0.0005 (8)
C20.0430 (9)0.0367 (9)0.0463 (10)−0.0020 (7)0.0035 (7)−0.0019 (8)
C30.0487 (9)0.0389 (9)0.0379 (9)−0.0027 (7)0.0094 (7)−0.0017 (7)
C40.0427 (9)0.0431 (9)0.0445 (10)−0.0044 (7)0.0089 (8)−0.0045 (8)
C50.0413 (9)0.0364 (9)0.0482 (10)−0.0045 (8)0.0021 (8)−0.0038 (8)
C60.0445 (9)0.0393 (9)0.0466 (10)−0.0038 (8)0.0059 (8)0.0007 (8)
C70.0467 (10)0.0562 (11)0.0559 (11)0.0022 (9)0.0081 (9)0.0100 (9)
C80.0515 (11)0.0690 (13)0.0716 (14)0.0094 (10)0.0111 (10)0.0070 (11)
C90.0635 (13)0.0747 (13)0.0692 (14)−0.0002 (11)0.0281 (11)0.0056 (11)
C100.0703 (13)0.0761 (14)0.0635 (13)0.0015 (11)0.0192 (11)0.0218 (11)
C110.0564 (11)0.0520 (11)0.0589 (12)0.0038 (9)0.0092 (9)0.0108 (9)
C120.0482 (10)0.0476 (10)0.0445 (10)0.0023 (8)0.0084 (8)0.0031 (8)
C130.0719 (13)0.0543 (12)0.0687 (14)0.0009 (10)0.0264 (10)−0.0070 (10)
C140.0773 (14)0.0734 (15)0.0873 (17)0.0169 (13)0.0319 (12)−0.0070 (12)
C150.0540 (12)0.1010 (18)0.0580 (13)0.0167 (13)0.0167 (10)0.0003 (12)
C160.0489 (11)0.0859 (16)0.0743 (15)−0.0054 (11)0.0151 (10)0.0106 (12)
C170.0522 (11)0.0547 (11)0.0727 (14)0.0007 (9)0.0144 (10)0.0062 (10)
C180.0399 (9)0.0406 (9)0.0450 (10)−0.0033 (7)0.0106 (7)−0.0037 (8)
C190.0503 (10)0.0482 (10)0.0487 (11)0.0018 (8)0.0100 (8)−0.0028 (8)
C200.0543 (11)0.0626 (12)0.0510 (11)−0.0020 (10)0.0032 (9)0.0056 (10)
C210.0557 (11)0.0582 (12)0.0752 (15)0.0094 (10)0.0050 (10)0.0093 (11)
C220.0857 (15)0.0630 (13)0.0764 (16)0.0308 (12)0.0173 (12)−0.0053 (11)
C230.0802 (13)0.0641 (12)0.0503 (12)0.0166 (11)0.0125 (10)−0.0083 (10)
C240.0503 (10)0.0459 (10)0.0564 (11)−0.0014 (9)0.0047 (9)−0.0047 (9)
Geometric parameters (Å, º) top
O1—C11.3523 (18)C11—H110.9300
O1—C41.4352 (18)C12—C131.377 (2)
O2—C51.2064 (17)C12—C171.378 (2)
N1—C241.140 (2)C13—C141.368 (3)
C1—C21.335 (2)C13—H130.9300
C1—C121.464 (2)C14—C151.363 (3)
C2—C241.403 (2)C14—H140.9300
C2—C31.514 (2)C15—C161.359 (3)
C3—C181.502 (2)C15—H150.9300
C3—C41.539 (2)C16—C171.375 (2)
C3—H30.9800C16—H160.9300
C4—C51.516 (2)C17—H170.9300
C4—H40.9800C18—C231.375 (2)
C5—C61.481 (2)C18—C191.379 (2)
C6—C111.377 (2)C19—C201.376 (2)
C6—C71.384 (2)C19—H190.9300
C7—C81.376 (2)C20—C211.359 (3)
C7—H70.9300C20—H200.9300
C8—C91.362 (3)C21—C221.354 (3)
C8—H80.9300C21—H210.9300
C9—C101.363 (3)C22—C231.377 (3)
C9—H90.9300C22—H220.9300
C10—C111.373 (2)C23—H230.9300
C10—H100.9300
C1—O1—C4108.15 (11)C6—C11—H11119.9
C2—C1—O1112.48 (14)C13—C12—C17118.86 (16)
C2—C1—C12132.09 (15)C13—C12—C1119.57 (16)
O1—C1—C12115.42 (13)C17—C12—C1121.57 (16)
C1—C2—C24127.47 (15)C14—C13—C12120.16 (19)
C1—C2—C3110.19 (13)C14—C13—H13119.9
C24—C2—C3122.34 (14)C12—C13—H13119.9
C18—C3—C2111.91 (12)C15—C14—C13120.7 (2)
C18—C3—C4115.79 (13)C15—C14—H14119.7
C2—C3—C499.09 (12)C13—C14—H14119.7
C18—C3—H3109.9C16—C15—C14119.74 (18)
C2—C3—H3109.9C16—C15—H15120.1
C4—C3—H3109.9C14—C15—H15120.1
O1—C4—C5109.25 (12)C15—C16—C17120.32 (19)
O1—C4—C3106.39 (12)C15—C16—H16119.8
C5—C4—C3112.63 (13)C17—C16—H16119.8
O1—C4—H4109.5C16—C17—C12120.24 (18)
C5—C4—H4109.5C16—C17—H17119.9
C3—C4—H4109.5C12—C17—H17119.9
O2—C5—C6121.97 (15)C23—C18—C19117.96 (15)
O2—C5—C4120.00 (14)C23—C18—C3120.79 (15)
C6—C5—C4118.02 (14)C19—C18—C3121.13 (14)
C11—C6—C7118.72 (16)C20—C19—C18120.66 (16)
C11—C6—C5118.71 (15)C20—C19—H19119.7
C7—C6—C5122.57 (15)C18—C19—H19119.7
C8—C7—C6120.46 (17)C21—C20—C19120.59 (18)
C8—C7—H7119.8C21—C20—H20119.7
C6—C7—H7119.8C19—C20—H20119.7
C9—C8—C7120.05 (18)C22—C21—C20119.37 (18)
C9—C8—H8120.0C22—C21—H21120.3
C7—C8—H8120.0C20—C21—H21120.3
C8—C9—C10119.96 (18)C21—C22—C23120.77 (18)
C8—C9—H9120.0C21—C22—H22119.6
C10—C9—H9120.0C23—C22—H22119.6
C9—C10—C11120.62 (18)C18—C23—C22120.63 (18)
C9—C10—H10119.7C18—C23—H23119.7
C11—C10—H10119.7C22—C23—H23119.7
C10—C11—C6120.17 (17)N1—C24—C2177.0 (2)
C10—C11—H11119.9
C4—O1—C1—C2−9.45 (18)C8—C9—C10—C110.2 (3)
C4—O1—C1—C12169.86 (13)C9—C10—C11—C60.6 (3)
O1—C1—C2—C24177.16 (15)C7—C6—C11—C10−0.6 (3)
C12—C1—C2—C24−2.0 (3)C5—C6—C11—C10179.74 (17)
O1—C1—C2—C3−3.50 (19)C2—C1—C12—C13153.06 (19)
C12—C1—C2—C3177.34 (16)O1—C1—C12—C13−26.1 (2)
C1—C2—C3—C18−109.07 (15)C2—C1—C12—C17−26.5 (3)
C24—C2—C3—C1870.31 (19)O1—C1—C12—C17154.34 (15)
C1—C2—C3—C413.56 (16)C17—C12—C13—C141.0 (3)
C24—C2—C3—C4−167.06 (15)C1—C12—C13—C14−178.61 (17)
C1—O1—C4—C5−103.83 (13)C12—C13—C14—C15−1.1 (3)
C1—O1—C4—C318.00 (16)C13—C14—C15—C160.6 (3)
C18—C3—C4—O1101.41 (15)C14—C15—C16—C170.1 (3)
C2—C3—C4—O1−18.39 (15)C15—C16—C17—C12−0.2 (3)
C18—C3—C4—C5−138.92 (14)C13—C12—C17—C16−0.3 (3)
C2—C3—C4—C5101.28 (14)C1—C12—C17—C16179.27 (16)
O1—C4—C5—O24.62 (19)C2—C3—C18—C23−103.03 (18)
C3—C4—C5—O2−113.38 (16)C4—C3—C18—C23144.42 (16)
O1—C4—C5—C6−176.36 (12)C2—C3—C18—C1972.97 (17)
C3—C4—C5—C665.64 (17)C4—C3—C18—C19−39.6 (2)
O2—C5—C6—C117.9 (2)C23—C18—C19—C200.0 (2)
C4—C5—C6—C11−171.09 (15)C3—C18—C19—C20−176.12 (14)
O2—C5—C6—C7−171.69 (15)C18—C19—C20—C210.5 (3)
C4—C5—C6—C79.3 (2)C19—C20—C21—C22−0.3 (3)
C11—C6—C7—C8−0.1 (3)C20—C21—C22—C23−0.4 (3)
C5—C6—C7—C8179.46 (16)C19—C18—C23—C22−0.7 (3)
C6—C7—C8—C91.0 (3)C3—C18—C23—C22175.45 (16)
C7—C8—C9—C10−1.0 (3)C21—C22—C23—C180.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···N1i0.932.633.487 (2)154
C21—H21···O2ii0.932.583.277 (2)132
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···N1i0.932.633.487 (2)153.9
C21—H21···O2ii0.932.583.277 (2)131.7
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2.
 

Acknowledgements

The authors thank Sophisticated Analytic Instrumentation Facility (SAIF), IIT Madras, Chennai, for single-crystal X-ray intensity data collection. RRK thanks the University Grants Commission, New Delhi, for funds through Major Research Project F. No. 42-242/2013 (SR).

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ISSN: 2056-9890
Volume 71| Part 9| September 2015| Pages o663-o664
https://doi.org/10.1107/S2056989015014887
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