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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1′-Methyl-4′-(4-methyl­phen­yl)di­spiro­[1-benzo­pyran-3(4H),3′-pyrrolidine-2′,3′′-indoline]-2,2′′-dione

aDepartment of Physics, C. Abdul Hakeem College of Engineering & Technology, Melvisharam, Vellore 632 509, India, bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: smurugavel27@gmail.com

(Received 28 November 2011; accepted 29 November 2011; online 3 December 2011)

In the title compound, C27H24N2O3, the pyrroldine ring adopts a twist conformation, while the six-membered pyran­one ring of the coumarin ring system is in a sofa conformation. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion R22(8) dimers. These dimers are further connected via C—H⋯O hydrogen bonds.

Related literature

For applications of pyrrolidine derivatives, see: Huryn et al. (1991[Huryn, D. M., Trost, B. M. & Fleming, I. (1991). Comp. Org. Synth. 1, 64-74.]); Suzuki et al. (1994[Suzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119-6122.]); Waldmann (1995[Waldmann, H. (1995). Synlett. pp. 133-141.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]) and for asymmetry parameters, see: Duax et al. (1976[Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271-383. New York: John Wiley.]). For closely related pyrrolidine structures, see: Selvanayagam et al. (2011[Selvanayagam, S., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o751.]); Ali et al. (2010[Ali, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o2533-o2534.]). For hydrogen-bond 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.]).

[Scheme 1]

Experimental

Crystal data
  • C27H24N2O3

  • Mr = 424.48

  • Monoclinic, P 21 /c

  • a = 10.4543 (3) Å

  • b = 14.6018 (4) Å

  • c = 14.7266 (4) Å

  • β = 104.043 (2)°

  • V = 2180.85 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.26 × 0.23 × 0.18 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.978, Tmax = 0.985

  • 30221 measured reflections

  • 7055 independent reflections

  • 4544 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.153

  • S = 1.02

  • 7055 reflections

  • 291 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.86 2.02 2.874 (1) 174
C5—H5B⋯O3ii 0.96 2.59 3.407 (2) 143
Symmetry codes: (i) -x+2, -y+2, -z; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Highly functionalized pyrrolidines have gained much interest in the past few years as they constitute the main structural element of many natural and synthetic pharmacologically active compounds (Waldmann, 1995). Optically active pyrrolidines have been used as intermediates, chiral ligands or auxiliaries in controlled asymmetric synthesis (Suzuki et al., 1994; Huryn et al., 1991). In view of this importance, the crystal structure of the title compound has been carried out and the results are presented here.

The title compound consists of a pyrrolidine ring connected to a oxindole ring system at C1, a coumarine moiety at C2 and a benzene ring at C3. The X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig.1.

The pyrrolidine (N1/C1–C4) ring adopts a twist conformation , with twist about the C4—N1 bond; the puckering parameters (Cremer & Pople, 1975), q2 = 0.4216 (14) Å and ϕ2 = 156.9 (2)°, and asymmetry parameters (Duax et al., 1976) ΔC2[C4—N1] = 5.0 Å. The six membered pyranone ring (O2/C2/C13/C14/C19/C20) of the coumarine moiety adopts screw-boat conformation as indicated from the puckering parameters: Q = 0.5296 (15) Å, θ = 65.9 (2)° and ϕ = 215.9 (2)°. The oxindole unit (N2/C1/C6–C12) is essentially planar [maximum deviation = 0.048 (1) Å for the C1 atom] and is oriented at a dihedral angles of 87.1 (1)° and 28.6 (1)°, respectively, with the pyrrolidine and coumarine rings. The sum of angles at N1 of the pyrrolidine ring (337°) is in accordance with sp3 hybridization, and the sum of angles at N2 of the indole moiety (360°) is in accordance with sp2 hybridization. The geometric parameters of the title molecule agrees well with those reported for similar structures (Selvanayagam et al., 2011; Ali et al., 2010).

Ihe molecular structure is stabilized by C3—H3···O3 and C13—H13A···O1 intramolecular hydrogen bonds, forming S(5) and S(6) ring motifs, respectively (Bernstein et al., 1995) (Table 1). The molecular structure is further stabilized by an intramolecular ππ interactions with Cg1—Cg2 seperation of 3.539 (1) Å. (Fig. 2; Cg1 and Cg2 are the centroids of the (N2/C1/C6/C7/C12) indole ring, (C14–C19) benzene ring, respectively). The crystal packing is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds. The molecules at x, y, z and 2-x, 2-y, -z are linked by N2—H2···O1 hydrogen bonds into cyclic centrosymmetric R22(8) dimers. This dimers are further connected by C5—H5B···O3 hydrogen bonds forming supramolecular zig zag chains along the c axis (Fig. 3).

Related literature top

For applications of pyrrolidine derivatives, see: Huryn et al. (1991 ); Suzuki et al. (1994); Waldmann (1995). For ring puckering parameters, see: Cremer & Pople (1975) and for asymmetry parameters, see: Duax et al. (1976). For closely related pyrrolidine structures, see: Selvanayagam et al. (2011); Ali et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of E-3-(4-methylbenzylidene)chroman-2-one (0.125 g, 0.5 mmol), isatin (0.08 g, 0.55 mmol) and N- methylglycine (0.025 g, 0.55 mmol) in toluene (5 ml) as solvent was allowed to reflux for 6 hours. After work up, the crude mass was purified by column chromatography to yield the pure product (0.195 g, 92% yield). The compound was recrystallized from ethyl acetate solvent. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a ethylacetate solution at room temperature.

Refinement top

H atoms were positioned geometrically, with N—H = 0.86 Å and and C—H = 0.93–0.98 Å and constrained to ride on their parent atom, with Uiso(H)=1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); 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 title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small cycles of arbitrary radius.
[Figure 2] Fig. 2. A view of the π···π interactions (dotted lines) in the molecular structure of the title compound. Cg1 and Cg2 are the centroids of the (N2/C1/C6/C7/C12) indole ring and (C14–C19) benzene ring, respectively.
[Figure 3] Fig. 3. View of supramolecular zig zag chain in (I) with N—H···O (blue dashed lines) and C—H···O (red dashed lines) hydrogen bonds along the c axis.[ Colour code: O(red), N(blue), C(black) & H(green).
1'-Methyl-4'-(4-methylphenyl)dispiro[1-benzopyran-3(4H),3'- pyrrolidine-2',3''-indoline]-2,2''-dione top
Crystal data top
C27H24N2O3F(000) = 896
Mr = 424.48Dx = 1.293 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7063 reflections
a = 10.4543 (3) Åθ = 2.0–31.2°
b = 14.6018 (4) ŵ = 0.09 mm1
c = 14.7266 (4) ÅT = 293 K
β = 104.043 (2)°Block, colourless
V = 2180.85 (10) Å30.26 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
7055 independent reflections
Radiation source: fine-focus sealed tube4544 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 10.0 pixels mm-1θmax = 31.2°, θmin = 2.0°
ω scansh = 1514
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2121
Tmin = 0.978, Tmax = 0.985l = 2021
30221 measured reflections
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0694P)2 + 0.398P]
where P = (Fo2 + 2Fc2)/3
7055 reflections(Δ/σ)max < 0.001
291 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C27H24N2O3V = 2180.85 (10) Å3
Mr = 424.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.4543 (3) ŵ = 0.09 mm1
b = 14.6018 (4) ÅT = 293 K
c = 14.7266 (4) Å0.26 × 0.23 × 0.18 mm
β = 104.043 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
7055 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4544 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.985Rint = 0.031
30221 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.153H-atom parameters constrained
S = 1.02Δρmax = 0.31 e Å3
7055 reflectionsΔρmin = 0.23 e Å3
291 parameters
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. 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 > 2sigma(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
C10.80511 (12)0.84780 (8)0.09959 (8)0.0326 (2)
C20.80733 (12)0.86879 (8)0.20643 (8)0.0335 (2)
C30.65980 (12)0.89026 (9)0.20385 (9)0.0367 (3)
H30.62070.83330.21970.044*
C40.59877 (13)0.90885 (11)0.10112 (10)0.0449 (3)
H4A0.50420.89890.08580.054*
H4B0.61660.97090.08410.054*
C50.63008 (17)0.84632 (12)0.04637 (10)0.0548 (4)
H5A0.53850.83130.06950.082*
H5B0.68300.80330.07050.082*
H5C0.64590.90700.06620.082*
C60.87724 (13)0.92422 (9)0.05686 (9)0.0383 (3)
C70.97873 (13)0.79028 (9)0.03856 (9)0.0382 (3)
C81.06331 (16)0.72827 (11)0.01407 (11)0.0528 (4)
H81.13110.74700.01250.063*
C91.04343 (19)0.63686 (12)0.03057 (13)0.0626 (5)
H91.10020.59320.01610.075*
C100.94146 (19)0.60908 (10)0.06787 (12)0.0586 (4)
H100.92910.54690.07670.070*
C110.85666 (16)0.67219 (9)0.09259 (10)0.0455 (3)
H110.78710.65320.11720.055*
C120.87840 (13)0.76409 (8)0.07963 (8)0.0348 (3)
C130.90158 (13)0.94596 (10)0.25105 (10)0.0450 (3)
H13A0.87881.00180.21520.054*
H13B0.89310.95730.31420.054*
C141.04058 (14)0.91967 (12)0.25330 (11)0.0520 (4)
C151.13597 (18)0.97997 (16)0.23772 (14)0.0717 (6)
H151.11521.04140.22540.086*
C161.2617 (2)0.9486 (2)0.24059 (18)0.0957 (8)
H161.32590.98930.23130.115*
C171.2920 (2)0.8584 (2)0.2570 (2)0.1000 (9)
H171.37660.83800.25780.120*
C181.19962 (18)0.79673 (18)0.27257 (14)0.0791 (6)
H181.22050.73520.28400.095*
C191.07479 (14)0.82966 (13)0.27055 (10)0.0544 (4)
C200.85238 (14)0.78283 (10)0.26401 (9)0.0418 (3)
C210.63774 (12)0.96203 (9)0.27238 (10)0.0395 (3)
C220.64635 (16)0.93919 (11)0.36474 (11)0.0509 (4)
H220.66570.87910.38430.061*
C230.62671 (17)1.00382 (13)0.42869 (12)0.0584 (4)
H230.63520.98640.49060.070*
C240.59504 (15)1.09288 (12)0.40314 (13)0.0560 (4)
C250.5856 (2)1.11562 (12)0.31114 (15)0.0677 (5)
H250.56371.17540.29150.081*
C260.60777 (18)1.05209 (11)0.24708 (12)0.0576 (4)
H260.60241.07030.18580.069*
C270.5729 (2)1.16348 (15)0.47218 (17)0.0806 (6)
H27A0.61501.21980.46240.121*
H27B0.60951.14200.53470.121*
H27C0.48001.17370.46350.121*
N10.66462 (11)0.84226 (8)0.05524 (8)0.0395 (2)
N20.97478 (11)0.88502 (8)0.02528 (8)0.0430 (3)
H21.02820.91480.00000.052*
O10.84748 (11)1.00547 (6)0.05046 (8)0.0525 (3)
O20.98473 (10)0.76670 (8)0.29036 (7)0.0546 (3)
O30.78215 (12)0.72821 (8)0.28723 (8)0.0607 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0345 (6)0.0302 (6)0.0358 (6)0.0025 (4)0.0135 (5)0.0040 (4)
C20.0307 (6)0.0370 (6)0.0351 (6)0.0028 (5)0.0122 (5)0.0013 (5)
C30.0304 (6)0.0405 (6)0.0426 (7)0.0013 (5)0.0154 (5)0.0039 (5)
C40.0343 (6)0.0549 (8)0.0459 (7)0.0033 (6)0.0108 (6)0.0029 (6)
C50.0553 (9)0.0659 (10)0.0397 (7)0.0022 (7)0.0051 (6)0.0038 (7)
C60.0412 (7)0.0345 (6)0.0434 (7)0.0018 (5)0.0184 (5)0.0055 (5)
C70.0409 (7)0.0403 (7)0.0343 (6)0.0031 (5)0.0110 (5)0.0006 (5)
C80.0489 (8)0.0610 (10)0.0504 (8)0.0121 (7)0.0157 (7)0.0087 (7)
C90.0666 (11)0.0519 (9)0.0654 (10)0.0217 (8)0.0080 (9)0.0158 (8)
C100.0752 (11)0.0342 (7)0.0583 (9)0.0090 (7)0.0007 (8)0.0044 (6)
C110.0564 (8)0.0341 (6)0.0432 (7)0.0043 (6)0.0066 (6)0.0020 (5)
C120.0406 (6)0.0319 (6)0.0315 (6)0.0005 (5)0.0079 (5)0.0013 (4)
C130.0368 (7)0.0510 (8)0.0505 (8)0.0090 (6)0.0172 (6)0.0151 (6)
C140.0345 (7)0.0732 (10)0.0499 (8)0.0107 (7)0.0131 (6)0.0233 (7)
C150.0484 (9)0.0934 (14)0.0787 (12)0.0280 (9)0.0260 (9)0.0347 (10)
C160.0436 (10)0.144 (2)0.1069 (18)0.0334 (13)0.0318 (11)0.0466 (17)
C170.0351 (9)0.155 (3)0.1101 (19)0.0022 (13)0.0174 (10)0.0376 (18)
C180.0427 (9)0.1165 (17)0.0735 (12)0.0177 (10)0.0055 (8)0.0151 (12)
C190.0348 (7)0.0841 (12)0.0422 (8)0.0019 (7)0.0050 (6)0.0116 (7)
C200.0441 (7)0.0485 (8)0.0344 (6)0.0056 (6)0.0126 (5)0.0054 (5)
C210.0312 (6)0.0437 (7)0.0471 (7)0.0024 (5)0.0159 (5)0.0019 (5)
C220.0566 (9)0.0508 (8)0.0516 (8)0.0114 (7)0.0253 (7)0.0060 (6)
C230.0592 (10)0.0708 (11)0.0512 (9)0.0109 (8)0.0248 (8)0.0019 (8)
C240.0411 (8)0.0614 (10)0.0685 (10)0.0054 (7)0.0190 (7)0.0145 (8)
C250.0757 (12)0.0464 (9)0.0819 (13)0.0145 (8)0.0208 (10)0.0001 (8)
C260.0701 (11)0.0485 (9)0.0561 (9)0.0107 (7)0.0189 (8)0.0069 (7)
C270.0697 (12)0.0794 (14)0.0981 (16)0.0079 (10)0.0307 (11)0.0328 (11)
N10.0348 (5)0.0465 (6)0.0364 (5)0.0024 (4)0.0073 (4)0.0027 (4)
N20.0459 (6)0.0404 (6)0.0509 (7)0.0014 (5)0.0274 (5)0.0064 (5)
O10.0583 (6)0.0341 (5)0.0744 (7)0.0032 (4)0.0344 (5)0.0138 (5)
O20.0464 (6)0.0712 (7)0.0436 (5)0.0159 (5)0.0056 (4)0.0086 (5)
O30.0682 (7)0.0571 (7)0.0645 (7)0.0054 (5)0.0314 (6)0.0256 (5)
Geometric parameters (Å, º) top
C1—N11.4577 (16)C13—H13A0.9700
C1—C121.5089 (17)C13—H13B0.9700
C1—C61.5621 (16)C14—C191.370 (3)
C1—C21.5975 (17)C14—C151.391 (2)
C2—C201.5240 (18)C15—C161.383 (3)
C2—C131.5356 (18)C15—H150.9300
C2—C31.5652 (17)C16—C171.363 (4)
C3—C211.5110 (18)C16—H160.9300
C3—C41.5169 (19)C17—C181.380 (4)
C3—H30.9800C17—H170.9300
C4—N11.4497 (18)C18—C191.384 (2)
C4—H4A0.9700C18—H180.9300
C4—H4B0.9700C19—O21.396 (2)
C5—N11.4529 (18)C20—O31.1892 (17)
C5—H5A0.9600C20—O21.3637 (17)
C5—H5B0.9600C21—C261.382 (2)
C5—H5C0.9600C21—C221.382 (2)
C6—O11.2243 (16)C22—C231.383 (2)
C6—N21.3467 (17)C22—H220.9300
C7—C81.3736 (19)C23—C241.372 (2)
C7—C121.3857 (18)C23—H230.9300
C7—N21.3964 (18)C24—C251.375 (3)
C8—C91.381 (2)C24—C271.505 (2)
C8—H80.9300C25—C261.382 (2)
C9—C101.374 (3)C25—H250.9300
C9—H90.9300C26—H260.9300
C10—C111.387 (2)C27—H27A0.9600
C10—H100.9300C27—H27B0.9600
C11—C121.3820 (18)C27—H27C0.9600
C11—H110.9300N2—H20.8600
C13—C141.496 (2)
N1—C1—C12111.83 (10)C2—C13—H13B109.7
N1—C1—C6113.05 (10)H13A—C13—H13B108.2
C12—C1—C6100.52 (9)C19—C14—C15118.22 (16)
N1—C1—C2102.96 (9)C19—C14—C13117.33 (14)
C12—C1—C2117.43 (10)C15—C14—C13124.44 (17)
C6—C1—C2111.50 (10)C16—C15—C14120.0 (2)
C20—C2—C13106.66 (11)C16—C15—H15120.0
C20—C2—C3110.37 (10)C14—C15—H15120.0
C13—C2—C3112.93 (10)C17—C16—C15120.2 (2)
C20—C2—C1108.58 (10)C17—C16—H16119.9
C13—C2—C1114.63 (10)C15—C16—H16119.9
C3—C2—C1103.64 (9)C16—C17—C18121.2 (2)
C21—C3—C4116.52 (11)C16—C17—H17119.4
C21—C3—C2115.59 (10)C18—C17—H17119.4
C4—C3—C2103.51 (10)C17—C18—C19117.7 (2)
C21—C3—H3106.9C17—C18—H18121.2
C4—C3—H3106.9C19—C18—H18121.2
C2—C3—H3106.9C14—C19—C18122.66 (18)
N1—C4—C3102.26 (11)C14—C19—O2120.77 (13)
N1—C4—H4A111.3C18—C19—O2116.53 (18)
C3—C4—H4A111.3O3—C20—O2117.19 (13)
N1—C4—H4B111.3O3—C20—C2125.69 (13)
C3—C4—H4B111.3O2—C20—C2117.12 (12)
H4A—C4—H4B109.2C26—C21—C22116.83 (14)
N1—C5—H5A109.5C26—C21—C3122.78 (13)
N1—C5—H5B109.5C22—C21—C3120.39 (12)
H5A—C5—H5B109.5C21—C22—C23121.36 (15)
N1—C5—H5C109.5C21—C22—H22119.3
H5A—C5—H5C109.5C23—C22—H22119.3
H5B—C5—H5C109.5C24—C23—C22121.72 (16)
O1—C6—N2125.79 (12)C24—C23—H23119.1
O1—C6—C1125.78 (11)C22—C23—H23119.1
N2—C6—C1108.39 (11)C23—C24—C25117.01 (15)
C8—C7—C12122.44 (13)C23—C24—C27122.04 (18)
C8—C7—N2127.98 (13)C25—C24—C27120.95 (18)
C12—C7—N2109.56 (11)C24—C25—C26121.77 (16)
C7—C8—C9117.18 (16)C24—C25—H25119.1
C7—C8—H8121.4C26—C25—H25119.1
C9—C8—H8121.4C21—C26—C25121.29 (16)
C10—C9—C8121.34 (15)C21—C26—H26119.4
C10—C9—H9119.3C25—C26—H26119.4
C8—C9—H9119.3C24—C27—H27A109.5
C9—C10—C11121.08 (15)C24—C27—H27B109.5
C9—C10—H10119.5H27A—C27—H27B109.5
C11—C10—H10119.5C24—C27—H27C109.5
C12—C11—C10118.15 (15)H27A—C27—H27C109.5
C12—C11—H11120.9H27B—C27—H27C109.5
C10—C11—H11120.9C4—N1—C5115.16 (11)
C11—C12—C7119.70 (12)C4—N1—C1107.14 (10)
C11—C12—C1130.64 (12)C5—N1—C1115.52 (11)
C7—C12—C1109.60 (10)C6—N2—C7111.83 (11)
C14—C13—C2109.89 (12)C6—N2—H2124.1
C14—C13—H13A109.7C7—N2—H2124.1
C2—C13—H13A109.7C20—O2—C19121.05 (12)
C14—C13—H13B109.7
N1—C1—C2—C20107.25 (11)C13—C14—C15—C16179.46 (17)
C12—C1—C2—C2016.07 (14)C14—C15—C16—C171.2 (3)
C6—C1—C2—C20131.25 (11)C15—C16—C17—C181.0 (4)
N1—C1—C2—C13133.62 (11)C16—C17—C18—C190.2 (4)
C12—C1—C2—C13103.06 (13)C15—C14—C19—C180.3 (2)
C6—C1—C2—C1312.12 (15)C13—C14—C19—C18178.73 (15)
N1—C1—C2—C310.10 (11)C15—C14—C19—O2177.45 (14)
C12—C1—C2—C3133.42 (11)C13—C14—C19—O23.5 (2)
C6—C1—C2—C3111.40 (11)C17—C18—C19—C140.5 (3)
C20—C2—C3—C2198.57 (13)C17—C18—C19—O2177.40 (18)
C13—C2—C3—C2120.72 (15)C13—C2—C20—O3138.05 (15)
C1—C2—C3—C21145.34 (11)C3—C2—C20—O315.04 (19)
C20—C2—C3—C4132.81 (11)C1—C2—C20—O397.92 (16)
C13—C2—C3—C4107.91 (13)C13—C2—C20—O242.67 (15)
C1—C2—C3—C416.72 (12)C3—C2—C20—O2165.68 (11)
C21—C3—C4—N1166.01 (10)C1—C2—C20—O281.35 (14)
C2—C3—C4—N137.96 (13)C4—C3—C21—C2622.73 (19)
N1—C1—C6—O155.83 (18)C2—C3—C21—C2699.17 (16)
C12—C1—C6—O1175.18 (14)C4—C3—C21—C22156.91 (13)
C2—C1—C6—O159.61 (18)C2—C3—C21—C2281.19 (16)
N1—C1—C6—N2122.03 (12)C26—C21—C22—C230.4 (2)
C12—C1—C6—N22.69 (13)C3—C21—C22—C23179.90 (14)
C2—C1—C6—N2122.52 (12)C21—C22—C23—C241.4 (3)
C12—C7—C8—C91.1 (2)C22—C23—C24—C251.0 (3)
N2—C7—C8—C9176.91 (14)C22—C23—C24—C27179.71 (17)
C7—C8—C9—C101.5 (2)C23—C24—C25—C260.4 (3)
C8—C9—C10—C111.7 (3)C27—C24—C25—C26178.90 (18)
C9—C10—C11—C120.7 (2)C22—C21—C26—C251.0 (2)
C10—C11—C12—C73.2 (2)C3—C21—C26—C25178.70 (15)
C10—C11—C12—C1179.77 (13)C24—C25—C26—C211.4 (3)
C8—C7—C12—C113.5 (2)C3—C4—N1—C5177.27 (12)
N2—C7—C12—C11174.86 (12)C3—C4—N1—C147.26 (13)
C8—C7—C12—C1178.92 (13)C12—C1—N1—C4162.40 (10)
N2—C7—C12—C12.76 (14)C6—C1—N1—C485.00 (12)
N1—C1—C12—C1153.82 (18)C2—C1—N1—C435.44 (12)
C6—C1—C12—C11174.04 (13)C12—C1—N1—C567.79 (14)
C2—C1—C12—C1164.87 (18)C6—C1—N1—C544.80 (15)
N1—C1—C12—C7123.46 (11)C2—C1—N1—C5165.25 (11)
C6—C1—C12—C73.23 (13)O1—C6—N2—C7176.60 (14)
C2—C1—C12—C7117.86 (11)C1—C6—N2—C71.27 (15)
C20—C2—C13—C1457.15 (15)C8—C7—N2—C6179.11 (14)
C3—C2—C13—C14178.55 (11)C12—C7—N2—C60.90 (16)
C1—C2—C13—C1463.05 (16)O3—C20—O2—C19176.49 (13)
C2—C13—C14—C1936.75 (18)C2—C20—O2—C194.17 (18)
C2—C13—C14—C15142.23 (15)C14—C19—O2—C2021.8 (2)
C19—C14—C15—C160.5 (3)C18—C19—O2—C20160.33 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.022.874 (1)174
C5—H5B···O3ii0.962.593.407 (2)143
Symmetry codes: (i) x+2, y+2, z; (ii) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC27H24N2O3
Mr424.48
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)10.4543 (3), 14.6018 (4), 14.7266 (4)
β (°) 104.043 (2)
V3)2180.85 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.26 × 0.23 × 0.18
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.978, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
30221, 7055, 4544
Rint0.031
(sin θ/λ)max1)0.728
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.153, 1.02
No. of reflections7055
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.23

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.022.874 (1)174.4
C5—H5B···O3ii0.962.593.407 (2)142.6
Symmetry codes: (i) x+2, y+2, z; (ii) x, y+3/2, z1/2.
 

Footnotes

Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

First citationAli, M. A., Ismail, R., Tan, S. C., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o2533–o2534.  Web of Science CSD CrossRef IUCr Journals
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  CrossRef CAS Web of Science
First citationBruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationDuax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271–383. New York: John Wiley.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationHuryn, D. M., Trost, B. M. & Fleming, I. (1991). Comp. Org. Synth. 1, 64–74.
First citationSelvanayagam, S., Ravikumar, K., Saravanan, P. & Raghunathan, R. (2011). Acta Cryst. E67, o751.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationSuzuki, H., Aoyagi, S. & Kibayashi, C. (1994). Tetrahedron Lett. 35, 6119–6122.  CrossRef CAS Web of Science
First citationWaldmann, H. (1995). Synlett. pp. 133–141.  CrossRef

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
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds