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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 68| Part 7| July 2012| Page o2098
https://doi.org/10.1107/S1600536812024506

1-Benzyl-3-[(4-methyl­phen­yl)imino]­indolin-2-one

Adebomi A. Ikotun,a Pius O. Adelanib and Gabriel O. Egharevbac*

aChemistry and Industrial Chemistry Department, Bowen University, Iwo, Nigeria, bDepartment of Civil Engineering and Geological Sciences and Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA, and cChemistry Department, Obafemi Awolowo University, Ile-ife, Nigeria
*Correspondence e-mail: gegharev@yahoo.com

(Received 13 May 2012; accepted 29 May 2012; online 13 June 2012)

In the title compound, C22H18N2O, the phenyl and tolyl rings make dihedral angles of 84.71 (7) and 65.11 (6)°, respectively, with the isatin group. The aromatic rings make a dihedral angle of 60.90 (8)°. The imino C=N double bond, exists in an E conformation. In the crystal, mol­ecules are linked by weak π–π stacking inter­actions [centroid–centroid distance = 3.6598 (13) Å].

Related literature

For background to isatin, its derivatives and their biological significance, see: Chazeau et al. (1992[Chazeau, V., Gussac, M. & Boucherle, A. (1992). Eur. J. Med. Chem. 27, 615-625.]); Igosheva et al. (2004[Igosheva, N., Matta, S. & Glover, V. (2004). Physiol. Behav. 80, 665-668.]); Medvedev et al. (1996[Medvedev, A. G., Clow, A., Sandler, M. & Glover, V. (1996). Biochem. Pharmacol. 52, 385-391.]); Abele et al. (2003[Abele, E., Abele, R., Dzenitis, O. & Lukevics, E. (2003). Chem. Heterocycl. Compd, 39, 3-35.]). For metal complexes of isatin derivatives and their biological significance, see: Rodriguez-Arguelles et al. (2004[Rodriguez-Arguelles, M. C., Ferrari, M. B., Bisceglie, F., Pelizzi, C., Pelosi, G., Pinelli, S. & Sassi, M. (2004). J. Inorg. Biochem. 98, 313-321.]); Singh et al. (2005[Singh, R. V., Fahmi, N. & Biyala, M. K. (2005). J. Iran. Chem. Soc. 2, 40-46.]); Chohan et al. (2006[Chohan, Z. H., Shaikh, A. U. & Naseer, M. M. (2006). Appl. Organomet. Chem. 20, 729-739.]); Adetoye et al. (2009[Adetoye, A. A., Egharevba, G. O., Obafemi, C. A. & Kelly, D. R. (2009). Toxicol. Environ. Chem. 91, 837-846.]); Ikotun et al. (2012[Ikotun, A. A., Egharevba, G. O., Obafemi, C. A. & Owoseni, O. O. (2012). J. Chem. Pharm. 4, 416-422.]). For N-benzyl isatin, its derivatives and biological significance, see Akkurt et al. (2006[Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.]); Jarrahpour & Khalili (2007[Jarrahpour, A. & Khalili, D. (2007). Tetrahedron Lett. 48, 7140-7143.]); Cao et al. (2009[Cao, J., Gao, H., Bemis, G., Salituro, F., Ledeboer, M., Harrington, E., Wilke, S., Taslimi, P., Pazhanisamy, S., Xie, X., Jacobs, M. & Green, J. (2009). Bioorg. Med. Chem. Lett. 19, 2891-2895.]).

[Scheme 1]

Experimental

Crystal data

  • C22H18N2O

  • Mr = 326.38

  • Monoclinic, P 21 /c

  • a = 10.174 (2) Å

  • b = 15.086 (4) Å

  • c = 11.714 (3) Å

  • β = 113.596 (3)°

  • V = 1647.5 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.04 × 0.02 × 0.01 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • 18815 measured reflections

  • 3763 independent reflections

  • 2456 reflections with I > 2σ(I)

  • Rint = 0.067
Refinement

  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.105

  • S = 0.92

  • 3763 reflections

  • 227 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812024506/bx2411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812024506/bx2411Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812024506/bx2411Isup3.cml

checkCIF report


Comment top

Indole-2, 3-dione commonly known as isatin is an endogenous indole present in mammalian tissues and fluids (Igosheva et al., 2004). It has largely been used as a versatile reagent in organic synthesis, to obtain heterocyclic compounds, and as a raw material for drugs (Abele et al., 2003). Several novel Schiff bases of isatin have been reported with a variety of pharmacological actions, including anticonvulsant, antimicrobial and antiviral activities, inhibition of monoamine oxidase (Medvedev et al., 1996). The study of the metal complexes of the Schiff base ligands derived from isatin and their biological applications has also received much attention (Singh et al., 2005; Chohan et al., 2006; Ikotun et al., 2012). Some first row transition metal complexes of the Schiff base of isatin derivatives were designed, prepared and characterized by spectroscopic means (Adetoye et al., 2009). The significance of these metal complexes of isatin derivatives has even been extended to the design of novel anticancer drugs (Rodriguez-Arguelles et al., 2004). N-benzylindole-2, 3-dione (N-benzylisatin) has also been prepared and the X-ray crystallographic structure has been established (Akkurt et al., 2006). N-alkylated isatins have interesting pharmacological activities such as antibacterial and anticancer (Chazeau et al., 1992). They are also reversible and competitive inhibitors of monoamine oxidase A and B (Medvedev et al., 1996). Some mono- and bis-spiro-b- benzylisatin have been prepared and characterized by spectroscopic means (Jarrahpour et al., 2007). A series of N-benzyl isatin oximes have also been developed as inhibitors of the mitogen-activated kinase, KNK3 (Cao et al., 2009). Thus the motivation and need to design novel Schiff bases of N-benzyl isatin, which would be of great biological significance, is the propelling force for this research. In the title compound , C22H18N2O, Fig. 1, the phenyl and benzene rings make dihedral angles of 84.71 (7)° and 65.11 (6)° with isatin group respectively. The aromatic rings make a dihedral angle of 60.90 (8)°.The imino C═N double bond, exists in an E conformation. In the crystal the molecules are linked by weak π—π stacking interaction (centroid-centroid distance 3.6598 (13) Å (Cg1=C4/C5/C6/C7/C8/C9 ; Cg2i=C17/C18/C19/C20/C21/C22, symmetry code (i): x,1/2-y, 1/2+z), Fig. 2.

Related literature top

For background to isatin, its derivatives and their biological significance, see: Chazeau et al. (1992); Igosheva et al. (2004); Medvedev et al. (1996); Abele et al. (2003). For metal complexes of isatin derivatives and their biological significance, see: Rodriguez-Arguelles et al. (2004); Singh et al. (2005); Chohan et al. (2006); Adetoye et al. (2009); Ikotun et al. (2012). For N-benzyl isatin, its derivatives and their biological significance, see Akkurt et al. (2006); Jarrahpour & Khalili (2007); Cao et al. (2009).

Experimental top

N-benzylisatin was first prepared and recrystallized in ethanol using the method of Akkurt et al., 2006 with slight modifications. N-benzylisatin (2.00 g; 8.44 mmol) was then dissolved in 30 ml hot ethanol. P-toluidine (0.90 g; 8.44 mmol) was dissolved in 10 ml ethanol. The solutions were mixed and refluxed for 6 h. The solution was allowed to cool and the deep orange solid was filtered under vacuum. The product was purified with flash column chromatography and the orange crystal as analyzed. The product was obtained at a yield of 78% (2.13 g). Flash Column Chromatographic purification of the product was carried out using a mixture of chloroform: diethyl ether (50%:50%) and single X-ray suitable crystals were got after the solvent was evaporated under vacuum.

Refinement top

The H atoms of the water molecule were located on a Fourier difference map, restrained by DFIX command 0.85 Å for O— H distances and by DFIX 1.39 Å for H···H distance, and refined as riding with Uiso(H) = 1.5Ueq(O). Other atoms were placed in their calculated positions, with C—H = 0.93 or 0.96 Å, and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C).

Structure description top

Indole-2, 3-dione commonly known as isatin is an endogenous indole present in mammalian tissues and fluids (Igosheva et al., 2004). It has largely been used as a versatile reagent in organic synthesis, to obtain heterocyclic compounds, and as a raw material for drugs (Abele et al., 2003). Several novel Schiff bases of isatin have been reported with a variety of pharmacological actions, including anticonvulsant, antimicrobial and antiviral activities, inhibition of monoamine oxidase (Medvedev et al., 1996). The study of the metal complexes of the Schiff base ligands derived from isatin and their biological applications has also received much attention (Singh et al., 2005; Chohan et al., 2006; Ikotun et al., 2012). Some first row transition metal complexes of the Schiff base of isatin derivatives were designed, prepared and characterized by spectroscopic means (Adetoye et al., 2009). The significance of these metal complexes of isatin derivatives has even been extended to the design of novel anticancer drugs (Rodriguez-Arguelles et al., 2004). N-benzylindole-2, 3-dione (N-benzylisatin) has also been prepared and the X-ray crystallographic structure has been established (Akkurt et al., 2006). N-alkylated isatins have interesting pharmacological activities such as antibacterial and anticancer (Chazeau et al., 1992). They are also reversible and competitive inhibitors of monoamine oxidase A and B (Medvedev et al., 1996). Some mono- and bis-spiro-b- benzylisatin have been prepared and characterized by spectroscopic means (Jarrahpour et al., 2007). A series of N-benzyl isatin oximes have also been developed as inhibitors of the mitogen-activated kinase, KNK3 (Cao et al., 2009). Thus the motivation and need to design novel Schiff bases of N-benzyl isatin, which would be of great biological significance, is the propelling force for this research. In the title compound , C22H18N2O, Fig. 1, the phenyl and benzene rings make dihedral angles of 84.71 (7)° and 65.11 (6)° with isatin group respectively. The aromatic rings make a dihedral angle of 60.90 (8)°.The imino C═N double bond, exists in an E conformation. In the crystal the molecules are linked by weak π—π stacking interaction (centroid-centroid distance 3.6598 (13) Å (Cg1=C4/C5/C6/C7/C8/C9 ; Cg2i=C17/C18/C19/C20/C21/C22, symmetry code (i): x,1/2-y, 1/2+z), Fig. 2.

For background to isatin, its derivatives and their biological significance, see: Chazeau et al. (1992); Igosheva et al. (2004); Medvedev et al. (1996); Abele et al. (2003). For metal complexes of isatin derivatives and their biological significance, see: Rodriguez-Arguelles et al. (2004); Singh et al. (2005); Chohan et al. (2006); Adetoye et al. (2009); Ikotun et al. (2012). For N-benzyl isatin, its derivatives and their biological significance, see Akkurt et al. (2006); Jarrahpour & Khalili (2007); Cao et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the labelled atoms; thermal ellipsoid are drawn at 50% probability level.
[Figure 2] Fig. 2. Part of the crystal structure showing π—π stacking interaction (centroid-centroid distance 3.6598 (13) Å (Cg1=C4/C5/C6/C7/C8/C9 ; Cg2i=C17/C18/C19/C20/C21/C22, symmetry code (i): x,1/2-y, 1/2+z).
1-Benzyl-3-[(4-methylphenyl)imino]indolin-2-one top
Crystal data top
C22H18N2OF(000) = 688
Mr = 326.38Dx = 1.316 Mg m−3
Monoclinic, P21/cMelting point: 427 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.174 (2) ÅCell parameters from 3069 reflections
b = 15.086 (4) Åθ = 2.6–25.6°
c = 11.714 (3) ŵ = 0.08 mm−1
β = 113.596 (3)°T = 296 K
V = 1647.5 (7) Å3Rectangular plate, orange
Z = 40.04 × 0.02 × 0.01 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.067
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
phi and ω scansh = −12→13
18815 measured reflectionsk = −19→19
3763 independent reflectionsl = −15→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0513P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
3763 reflectionsΔρmax = 0.35 e Å−3
227 parametersΔρmin = −0.31 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0075 (12)
Crystal data top
C22H18N2OV = 1647.5 (7) Å3
Mr = 326.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.174 (2) ŵ = 0.08 mm−1
b = 15.086 (4) ÅT = 296 K
c = 11.714 (3) Å0.04 × 0.02 × 0.01 mm
β = 113.596 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2456 reflections with I > 2σ(I)
18815 measured reflectionsRint = 0.067
3763 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.105H-atom parameters constrained
S = 0.92Δρmax = 0.35 e Å−3
3763 reflectionsΔρmin = −0.31 e Å−3
227 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
O10.30165 (11)0.19312 (7)0.89390 (10)0.0256 (3)
N10.23619 (13)0.32278 (8)0.77977 (12)0.0192 (3)
N20.06155 (13)0.22984 (8)0.95540 (12)0.0195 (3)
C18−0.15861 (16)0.18456 (10)0.97075 (14)0.0221 (4)
H18A−0.16100.13530.92230.027*
C19−0.26219 (17)0.19479 (11)1.01801 (15)0.0237 (4)
H19A−0.33540.15310.99840.028*
C6−0.10985 (17)0.48946 (10)0.72028 (14)0.0217 (4)
H6A−0.18860.52530.70850.026*
C80.09598 (16)0.45662 (10)0.67264 (14)0.0204 (4)
H8A0.15410.46940.63050.024*
C90.12438 (16)0.38541 (10)0.75280 (14)0.0179 (3)
C110.43743 (16)0.40255 (10)0.75565 (14)0.0197 (4)
C22−0.04756 (17)0.32009 (10)1.06994 (14)0.0226 (4)
H22A0.02360.36291.08720.027*
C5−0.08057 (16)0.41752 (10)0.80063 (14)0.0203 (4)
H5A−0.13940.40460.84210.024*
C100.34082 (17)0.32210 (10)0.72300 (15)0.0233 (4)
H10A0.29000.31900.63320.028*
H10B0.39960.26930.74990.028*
C17−0.05075 (16)0.24753 (10)0.99516 (14)0.0192 (3)
C40.03861 (16)0.36512 (10)0.81794 (14)0.0178 (3)
C20−0.25950 (16)0.26584 (10)1.09418 (14)0.0211 (4)
C7−0.02307 (16)0.50861 (10)0.65726 (14)0.0209 (4)
H7A−0.04490.55710.60380.025*
C21−0.15100 (17)0.32812 (10)1.11853 (15)0.0236 (4)
H21A−0.14760.37651.16880.028*
C30.09602 (16)0.28278 (10)0.88691 (14)0.0182 (3)
C20.22451 (16)0.25759 (10)0.85647 (14)0.0196 (3)
C160.52131 (17)0.42307 (11)0.87874 (15)0.0249 (4)
H16A0.51740.38730.94200.030*
C120.44522 (17)0.45665 (12)0.66264 (16)0.0289 (4)
H12A0.39030.44350.57950.035*
C130.53422 (18)0.53003 (12)0.69284 (18)0.0339 (5)
H13A0.53860.56600.63000.041*
C150.61098 (18)0.49624 (12)0.90861 (17)0.0315 (4)
H15A0.66760.50900.99160.038*
C140.61647 (18)0.54999 (11)0.81580 (18)0.0332 (5)
H14A0.67550.59970.83590.040*
C23−0.36913 (18)0.27314 (12)1.15025 (16)0.0290 (4)
H23A−0.35150.32591.20000.044*
H23B−0.36220.22231.20160.044*
H23C−0.46350.27591.08480.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0239 (6)0.0211 (6)0.0327 (7)0.0069 (5)0.0122 (5)0.0020 (5)
N10.0175 (7)0.0178 (7)0.0251 (7)0.0009 (5)0.0115 (6)0.0001 (5)
N20.0186 (7)0.0179 (7)0.0218 (7)−0.0012 (5)0.0077 (6)−0.0007 (6)
C180.0239 (9)0.0178 (8)0.0236 (9)−0.0010 (7)0.0084 (7)−0.0019 (7)
C190.0185 (8)0.0245 (9)0.0268 (9)−0.0041 (7)0.0076 (7)0.0006 (7)
C60.0198 (8)0.0183 (8)0.0271 (9)0.0023 (7)0.0094 (7)−0.0022 (7)
C80.0205 (8)0.0195 (8)0.0231 (8)−0.0037 (7)0.0108 (7)−0.0019 (7)
C90.0169 (8)0.0146 (8)0.0224 (8)−0.0011 (6)0.0080 (7)−0.0033 (6)
C110.0163 (8)0.0205 (8)0.0259 (9)0.0039 (6)0.0123 (7)0.0011 (7)
C220.0214 (9)0.0208 (9)0.0255 (9)−0.0043 (7)0.0091 (7)−0.0014 (7)
C50.0195 (8)0.0198 (8)0.0241 (9)−0.0014 (7)0.0112 (7)−0.0015 (7)
C100.0207 (9)0.0257 (9)0.0277 (9)0.0017 (7)0.0140 (7)−0.0037 (7)
C170.0194 (8)0.0183 (8)0.0188 (8)0.0027 (6)0.0067 (7)0.0041 (6)
C40.0172 (8)0.0158 (8)0.0201 (8)−0.0019 (6)0.0071 (7)−0.0020 (6)
C200.0189 (8)0.0239 (9)0.0192 (8)0.0017 (7)0.0065 (7)0.0027 (7)
C70.0240 (9)0.0161 (8)0.0221 (9)−0.0008 (7)0.0086 (7)0.0002 (6)
C210.0250 (9)0.0242 (9)0.0224 (9)−0.0011 (7)0.0102 (7)−0.0043 (7)
C30.0161 (8)0.0153 (8)0.0215 (8)−0.0018 (6)0.0057 (7)−0.0027 (6)
C20.0187 (8)0.0181 (8)0.0218 (8)−0.0018 (7)0.0078 (7)−0.0036 (7)
C160.0245 (9)0.0267 (9)0.0266 (9)0.0012 (7)0.0136 (8)0.0030 (7)
C120.0179 (8)0.0421 (11)0.0277 (9)0.0035 (8)0.0102 (7)0.0101 (8)
C130.0218 (9)0.0368 (11)0.0476 (12)0.0062 (8)0.0185 (9)0.0211 (9)
C150.0265 (10)0.0343 (10)0.0362 (11)−0.0052 (8)0.0152 (9)−0.0097 (8)
C140.0229 (9)0.0217 (9)0.0617 (13)−0.0011 (7)0.0238 (9)−0.0011 (9)
C230.0250 (9)0.0378 (10)0.0264 (9)−0.0001 (8)0.0125 (8)0.0007 (8)
Geometric parameters (Å, º) top
O1—C21.2160 (18)C22—H22A0.9300
N1—C21.3690 (19)C5—C41.393 (2)
N1—C91.4137 (19)C5—H5A0.9300
N1—C101.4636 (19)C10—H10A0.9700
N2—C31.2767 (19)C10—H10B0.9700
N2—C171.4210 (19)C4—C31.469 (2)
C18—C191.381 (2)C20—C211.389 (2)
C18—C171.392 (2)C20—C231.508 (2)
C18—H18A0.9300C7—H7A0.9300
C19—C201.388 (2)C21—H21A0.9300
C19—H19A0.9300C3—C21.534 (2)
C6—C51.389 (2)C16—C151.385 (2)
C6—C71.389 (2)C16—H16A0.9300
C6—H6A0.9300C12—C131.383 (2)
C8—C91.379 (2)C12—H12A0.9300
C8—C71.393 (2)C13—C141.379 (3)
C8—H8A0.9300C13—H13A0.9300
C9—C41.404 (2)C15—C141.375 (2)
C11—C161.385 (2)C15—H15A0.9300
C11—C121.389 (2)C14—H14A0.9300
C11—C101.511 (2)C23—H23A0.9600
C22—C211.388 (2)C23—H23B0.9600
C22—C171.394 (2)C23—H23C0.9600
C2—N1—C9110.69 (13)C5—C4—C3133.73 (14)
C2—N1—C10124.27 (13)C9—C4—C3106.64 (13)
C9—N1—C10124.73 (13)C19—C20—C21117.63 (15)
C3—N2—C17123.20 (13)C19—C20—C23120.58 (15)
C19—C18—C17120.45 (15)C21—C20—C23121.78 (15)
C19—C18—H18A119.8C6—C7—C8121.26 (15)
C17—C18—H18A119.8C6—C7—H7A119.4
C18—C19—C20121.47 (15)C8—C7—H7A119.4
C18—C19—H19A119.3C22—C21—C20121.84 (15)
C20—C19—H19A119.3C22—C21—H21A119.1
C5—C6—C7120.88 (15)C20—C21—H21A119.1
C5—C6—H6A119.6N2—C3—C4136.53 (14)
C7—C6—H6A119.6N2—C3—C2117.71 (13)
C9—C8—C7117.45 (14)C4—C3—C2105.65 (12)
C9—C8—H8A121.3O1—C2—N1126.74 (15)
C7—C8—H8A121.3O1—C2—C3126.97 (14)
C8—C9—C4122.25 (14)N1—C2—C3106.29 (13)
C8—C9—N1127.10 (14)C15—C16—C11120.69 (16)
C4—C9—N1110.64 (13)C15—C16—H16A119.7
C16—C11—C12118.72 (15)C11—C16—H16A119.7
C16—C11—C10120.68 (14)C13—C12—C11120.44 (17)
C12—C11—C10120.60 (15)C13—C12—H12A119.8
C21—C22—C17119.70 (14)C11—C12—H12A119.8
C21—C22—H22A120.1C14—C13—C12120.23 (16)
C17—C22—H22A120.1C14—C13—H13A119.9
C6—C5—C4118.71 (14)C12—C13—H13A119.9
C6—C5—H5A120.6C14—C15—C16120.09 (17)
C4—C5—H5A120.6C14—C15—H15A120.0
N1—C10—C11113.38 (12)C16—C15—H15A120.0
N1—C10—H10A108.9C15—C14—C13119.82 (17)
C11—C10—H10A108.9C15—C14—H14A120.1
N1—C10—H10B108.9C13—C14—H14A120.1
C11—C10—H10B108.9C20—C23—H23A109.5
H10A—C10—H10B107.7C20—C23—H23B109.5
C18—C17—C22118.88 (15)H23A—C23—H23B109.5
C18—C17—N2118.41 (14)C20—C23—H23C109.5
C22—C17—N2122.27 (14)H23A—C23—H23C109.5
C5—C4—C9119.44 (14)H23B—C23—H23C109.5

Experimental details

Crystal data
Chemical formulaC22H18N2O
Mr326.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)10.174 (2), 15.086 (4), 11.714 (3)
β (°) 113.596 (3)
V (Å3)1647.5 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.04 × 0.02 × 0.01
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		18815, 3763, 2456
Rint0.067
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.105, 0.92
No. of reflections3763
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.35, −0.31

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We appreciate Professor John A. Gladysz for benevolently facilitating AAI's visit to his laboratory at Texas A & M University during the course of this research and also all members of the Gladysz research group for their assistance towards a successful academic visit.

References

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ISSN: 2056-9890
Volume 68| Part 7| July 2012| Page o2098
https://doi.org/10.1107/S1600536812024506
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