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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

4′-Cyano­bi­phenyl-4-yl 7-di­ethyl­amino-2-oxo-2H-chromene-3-carboxyl­ate

aDeapartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India, bRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India, cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com

(Received 10 January 2013; accepted 16 January 2013; online 19 January 2013)

In the title compound, C27H22N2O4, the dihedral angles between the central benzene ring and the cyano­benzene ring and the 2H-coumarin ring system (r.m.s. deviation = 0.014 Å) are 22.95 (11) and 75.59 (8)°, respectively. Both terminal C atoms of the pendant diethyl­amino group lie to the same side of the coumarin ring system [deviations = 1.366 (2) and 1.266 (2) Å]. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds and a C—H⋯π inter­action, generating a three-dimensional network.

Related literature

For the biological properties of coumarin derivatives, see: Bhat et al. (2006[Bhat, M. A., Siddiqui, N. & Khan, S. A. (2006). Indian J. Pharm. Sci. 68, 120-124.]); Chimichi et al. (2002[Chimichi, S., Boccalini, M., Cosimelli, B., Viola, G., Vedaldi, D. & Dall Acqua, F. (2002). Tetrahedron Lett. 43, 7473-7476.]).

[Scheme 1]

Experimental

Crystal data
  • C27H22N2O4

  • Mr = 438.47

  • Triclinic, [P \overline 1]

  • a = 9.652 (3) Å

  • b = 10.252 (4) Å

  • c = 11.121 (4) Å

  • α = 87.214 (10)°

  • β = 86.358 (10)°

  • γ = 84.348 (11)°

  • V = 1091.9 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 300 K

  • 0.24 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.984

  • 10667 measured reflections

  • 3783 independent reflections

  • 2495 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.173

  • S = 0.97

  • 3783 reflections

  • 301 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.37 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O1i 0.93 2.53 3.446 (3) 170
C11—H11⋯N2ii 0.93 2.59 3.435 (3) 152
C16—H16⋯O1iii 0.93 2.54 3.465 (3) 177
C1—H1BCg3iv 0.96 2.82 3.626 (3) 142
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x-1, -y+2, -z+1; (iii) -x, -y+2, -z+2; (iv) x+1, y-1, z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Coumarins are well known for displaying a broad range of biological activities like anti- inflammatory, anticonvulsant (Bhat et al., 2006) and antitumor agents (Chimichi et al., 2002). As part of our studies in this area, we now report the synthesis and crystal structure (Fig. 1) of the title cyanobiphenyl coumarin, (I), derived from the reaction of 7-diethylamino coumarin.

The 2H-chromene ring (O2/C5–C13) system in (I) is almost planar, with a maximum deviation of 0.025 (2) Å for atom C13. The dihedral angle between 2H-chromene ring (O2/C5–C13) with the benzene(C15–C20) terminal benzene(C21—C26) rings are 75.59 (8)° and 56.02 (1)° respectively. The crystal structure is characterized by intermolecular C6—H6···O1, C11—H11···N2 and C16—H16···O1 hydrogen bonding and also features C—H..π [Cg(3)(C15–C20) interactions (Table.1). Crystal packing for the title compound with hydrogen bonds drawn as dashed lines (Fig. 2).

Related literature top

For the biological properties of coumarin derivatives, see: Bhat et al. (2006); Chimichi et al. (2002).

Experimental top

N,N-Dicyclohexylcarbodiimide (215 mg, 1.2 mmol) was added to a magnetically stirred solution of 7-(diethylamino) -2-oxo-2H-chromene -3-carboxylic acid (261 mg, 1 mmol), 4-cyano 4'-hydroxybiphenyl (195 mg, 1 mmol) and a catalytic quantity of N,N-dimethylaminopyrimidine (DMAP) in dried dichloromethane. Resultant reaction mixture was stirred further for 24 h at room temperature. Pure compound was obtained by aqueous workup and column chromatography. Colourless prisms were obtained from chloroform solution on slow evaporation at room temperature (m.p. 541 K).

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H, C—H = 0.97 Å for methylene H and C—H = 0.96 Å for methyl H,and refined using a riding model with Uiso(H) = 1.5Ueq(C) for methyl H and Uiso(H) = 1.2Ueq(C) for all other H.

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing for the title compound with hydrogen bonds drawn as dashed lines.
4'-Cyanobiphenyl-4-yl 7-diethylamino-2-oxo-2H-chromene-3-carboxylate top
Crystal data top
C27H22N2O4Z = 2
Mr = 438.47F(000) = 460
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Melting point: 541 K
a = 9.652 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.252 (4) ÅCell parameters from 3783 reflections
c = 11.121 (4) Åθ = 1.8–25.0°
α = 87.214 (10)°µ = 0.09 mm1
β = 86.358 (10)°T = 300 K
γ = 84.348 (11)°Prism, colourless
V = 1091.9 (6) Å30.24 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer
3783 independent reflections
Radiation source: fine-focus sealed tube2495 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω and ϕ scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1110
Tmin = 0.979, Tmax = 0.984k = 1212
10667 measured reflectionsl = 1313
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)] = 0.058H-atom parameters constrained
wR(F2) = 0.173 w = 1/[σ2(Fo2) + (0.1107P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3783 reflectionsΔρmax = 0.22 e Å3
301 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (4)
Crystal data top
C27H22N2O4γ = 84.348 (11)°
Mr = 438.47V = 1091.9 (6) Å3
Triclinic, P1Z = 2
a = 9.652 (3) ÅMo Kα radiation
b = 10.252 (4) ŵ = 0.09 mm1
c = 11.121 (4) ÅT = 300 K
α = 87.214 (10)°0.24 × 0.20 × 0.18 mm
β = 86.358 (10)°
Data collection top
Bruker SMART CCD
diffractometer
3783 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
2495 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.984Rint = 0.048
10667 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.173H-atom parameters constrained
S = 0.97Δρmax = 0.22 e Å3
3783 reflectionsΔρmin = 0.37 e Å3
301 parameters
Special details top

Experimental. 1H NMR (400Mz, TMS): δ 8.36(s, 1H), 7.44–7.65(m, 6H), 7.12–7.08(m, 3H), 6.34(m, 2H), 3.38(m, 4H), 1.10(m, 6H); Elemental analysis calculated for C27H22N2O4, C, 73.96; H, 5.06; N, 6.39; found C, 74.20; H, 5.32; N, 6.33.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O10.24765 (18)1.10054 (17)0.94063 (14)0.0535 (5)
O20.37525 (15)0.91308 (15)0.92731 (12)0.0417 (4)
O30.04165 (16)0.96402 (16)0.71953 (13)0.0503 (5)
O40.0195 (2)1.1161 (2)0.85320 (18)0.0753 (6)
N10.68882 (19)0.52702 (19)0.90485 (16)0.0457 (5)
N21.0656 (2)1.3764 (2)0.4192 (2)0.0641 (7)
C10.7967 (3)0.4011 (3)0.7316 (2)0.0668 (8)
H1A0.73130.44530.67820.100*
H1B0.82130.31300.70680.100*
H1C0.87890.44690.72910.100*
C20.7317 (3)0.3978 (2)0.8581 (2)0.0493 (6)
H2A0.65070.34850.86020.059*
H2B0.79800.35150.91090.059*
C30.7847 (3)0.5811 (3)0.9826 (2)0.0529 (7)
H3A0.83330.50941.02800.064*
H3B0.73080.63701.03990.064*
C40.8898 (3)0.6584 (3)0.9148 (2)0.0656 (8)
H4A0.94690.60260.86080.098*
H4B0.94740.69270.97060.098*
H4C0.84260.72960.86950.098*
C50.4066 (2)0.7908 (2)0.88368 (16)0.0342 (5)
C60.5309 (2)0.7249 (2)0.91367 (18)0.0393 (6)
H60.59010.76410.96070.047*
C70.5690 (2)0.5977 (2)0.87307 (18)0.0383 (5)
C80.4763 (2)0.5447 (2)0.7979 (2)0.0448 (6)
H80.49980.46170.76810.054*
C90.3544 (2)0.6131 (2)0.76906 (19)0.0425 (6)
H90.29650.57570.71950.051*
C100.3130 (2)0.7385 (2)0.81176 (17)0.0361 (5)
C110.1893 (2)0.8156 (2)0.78679 (18)0.0376 (5)
H110.12670.78240.73880.045*
C120.1576 (2)0.9373 (2)0.83021 (17)0.0366 (5)
C130.2546 (2)0.9931 (2)0.90192 (18)0.0380 (5)
C140.0264 (2)1.0177 (2)0.80661 (19)0.0449 (6)
C150.4115 (2)1.0844 (2)0.73193 (18)0.0441 (6)
H150.48901.08530.78610.053*
C160.2848 (2)1.0282 (2)0.76805 (18)0.0451 (6)
H160.27700.99110.84560.054*
C170.1706 (2)1.0274 (2)0.68882 (19)0.0416 (6)
C180.1806 (2)1.0826 (2)0.5739 (2)0.0481 (6)
H180.10221.08220.52080.058*
C190.3081 (2)1.1384 (3)0.53862 (19)0.0483 (6)
H190.31471.17570.46100.058*
C200.4266 (2)1.1403 (2)0.61565 (18)0.0392 (6)
C210.5644 (2)1.1962 (2)0.57555 (17)0.0384 (5)
C220.5909 (2)1.2058 (2)0.45324 (19)0.0473 (6)
H220.52021.17910.39640.057*
C230.7190 (3)1.2539 (3)0.4155 (2)0.0490 (6)
H230.73381.26050.33360.059*
C240.8261 (2)1.2927 (2)0.4976 (2)0.0442 (6)
C250.8024 (3)1.2853 (3)0.6196 (2)0.0567 (7)
H250.87331.31240.67610.068*
C260.6725 (3)1.2373 (3)0.6565 (2)0.0534 (7)
H260.65731.23250.73840.064*
C270.9608 (3)1.3402 (2)0.4561 (2)0.0490 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0521 (11)0.0481 (12)0.0611 (10)0.0095 (8)0.0207 (8)0.0165 (8)
O20.0338 (9)0.0459 (10)0.0452 (8)0.0071 (7)0.0118 (7)0.0110 (7)
O30.0396 (10)0.0559 (11)0.0541 (9)0.0177 (8)0.0193 (8)0.0138 (7)
O40.0577 (13)0.0671 (14)0.1019 (15)0.0276 (10)0.0357 (11)0.0404 (11)
N10.0342 (12)0.0484 (13)0.0530 (11)0.0099 (9)0.0095 (9)0.0056 (9)
N20.0480 (14)0.0701 (17)0.0754 (14)0.0078 (12)0.0270 (12)0.0109 (12)
C10.068 (2)0.0506 (18)0.0788 (18)0.0061 (14)0.0090 (15)0.0119 (13)
C20.0434 (15)0.0425 (15)0.0594 (14)0.0091 (12)0.0053 (11)0.0016 (11)
C30.0398 (15)0.0597 (18)0.0569 (13)0.0145 (12)0.0136 (11)0.0019 (12)
C40.0493 (18)0.076 (2)0.0709 (17)0.0032 (15)0.0055 (13)0.0118 (14)
C50.0326 (13)0.0376 (13)0.0321 (10)0.0006 (10)0.0022 (9)0.0031 (8)
C60.0272 (13)0.0503 (15)0.0402 (11)0.0010 (10)0.0060 (9)0.0051 (10)
C70.0288 (12)0.0451 (15)0.0392 (11)0.0047 (10)0.0013 (9)0.0000 (9)
C80.0362 (14)0.0435 (15)0.0537 (12)0.0052 (11)0.0062 (10)0.0079 (10)
C90.0345 (14)0.0462 (15)0.0476 (12)0.0006 (11)0.0094 (10)0.0076 (10)
C100.0296 (13)0.0418 (14)0.0364 (10)0.0004 (10)0.0047 (9)0.0019 (9)
C110.0309 (13)0.0460 (15)0.0363 (10)0.0018 (10)0.0079 (9)0.0019 (9)
C120.0319 (13)0.0412 (14)0.0361 (10)0.0022 (10)0.0066 (9)0.0022 (9)
C130.0344 (13)0.0426 (15)0.0361 (10)0.0045 (10)0.0054 (9)0.0042 (9)
C140.0419 (15)0.0454 (16)0.0473 (12)0.0046 (12)0.0115 (11)0.0078 (11)
C150.0358 (14)0.0542 (16)0.0403 (11)0.0034 (11)0.0019 (10)0.0026 (10)
C160.0452 (16)0.0518 (16)0.0366 (11)0.0054 (11)0.0093 (11)0.0044 (10)
C170.0361 (14)0.0406 (14)0.0475 (12)0.0081 (10)0.0137 (10)0.0053 (9)
C180.0355 (14)0.0567 (17)0.0491 (13)0.0081 (12)0.0002 (10)0.0014 (11)
C190.0398 (15)0.0617 (17)0.0394 (11)0.0094 (12)0.0030 (10)0.0090 (10)
C200.0361 (13)0.0407 (14)0.0394 (11)0.0044 (10)0.0050 (10)0.0004 (9)
C210.0341 (13)0.0407 (14)0.0389 (11)0.0039 (10)0.0047 (9)0.0005 (9)
C220.0365 (14)0.0634 (17)0.0392 (11)0.0073 (12)0.0019 (10)0.0004 (10)
C230.0471 (16)0.0574 (17)0.0420 (12)0.0027 (12)0.0122 (11)0.0013 (10)
C240.0322 (14)0.0456 (15)0.0544 (13)0.0025 (11)0.0115 (11)0.0003 (10)
C250.0391 (15)0.078 (2)0.0477 (13)0.0180 (13)0.0009 (11)0.0029 (12)
C260.0428 (16)0.0751 (19)0.0386 (12)0.0145 (13)0.0057 (11)0.0015 (11)
C270.0457 (16)0.0495 (16)0.0522 (13)0.0011 (12)0.0120 (12)0.0058 (11)
Geometric parameters (Å, º) top
O1—C131.196 (3)C9—C101.404 (3)
O2—C51.365 (3)C9—H90.9300
O2—C131.393 (3)C10—C111.401 (3)
O3—C141.370 (3)C11—C121.360 (3)
O3—C171.400 (3)C11—H110.9300
O4—C141.189 (3)C12—C131.443 (3)
N1—C71.360 (3)C12—C141.473 (3)
N1—C21.459 (3)C15—C161.374 (3)
N1—C31.470 (3)C15—C201.399 (3)
N2—C271.138 (3)C15—H150.9300
C1—C21.504 (4)C16—C171.367 (3)
C1—H1A0.9600C16—H160.9300
C1—H1B0.9600C17—C181.378 (3)
C1—H1C0.9600C18—C191.377 (3)
C2—H2A0.9700C18—H180.9300
C2—H2B0.9700C19—C201.384 (3)
C3—C41.493 (4)C19—H190.9300
C3—H3A0.9700C20—C211.482 (3)
C3—H3B0.9700C21—C261.381 (3)
C4—H4A0.9600C21—C221.397 (3)
C4—H4B0.9600C22—C231.368 (3)
C4—H4C0.9600C22—H220.9300
C5—C61.370 (3)C23—C241.377 (3)
C5—C101.405 (3)C23—H230.9300
C6—C71.408 (3)C24—C251.388 (3)
C6—H60.9300C24—C271.439 (3)
C7—C81.424 (3)C25—C261.380 (3)
C8—C91.358 (3)C25—H250.9300
C8—H80.9300C26—H260.9300
C5—O2—C13123.43 (16)C12—C11—H11118.9
C14—O3—C17117.47 (18)C10—C11—H11118.9
C7—N1—C2121.64 (19)C11—C12—C13120.2 (2)
C7—N1—C3121.2 (2)C11—C12—C14122.59 (19)
C2—N1—C3117.10 (19)C13—C12—C14117.3 (2)
C2—C1—H1A109.5O1—C13—O2114.84 (18)
C2—C1—H1B109.5O1—C13—C12128.9 (2)
H1A—C1—H1B109.5O2—C13—C12116.2 (2)
C2—C1—H1C109.5O4—C14—O3122.0 (2)
H1A—C1—H1C109.5O4—C14—C12127.6 (2)
H1B—C1—H1C109.5O3—C14—C12110.4 (2)
N1—C2—C1114.2 (2)C16—C15—C20121.6 (2)
N1—C2—H2A108.7C16—C15—H15119.2
C1—C2—H2A108.7C20—C15—H15119.2
N1—C2—H2B108.7C17—C16—C15119.31 (18)
C1—C2—H2B108.7C17—C16—H16120.3
H2A—C2—H2B107.6C15—C16—H16120.3
N1—C3—C4113.6 (2)C16—C17—C18121.0 (2)
N1—C3—H3A108.8C16—C17—O3121.06 (18)
C4—C3—H3A108.8C18—C17—O3117.9 (2)
N1—C3—H3B108.8C19—C18—C17119.2 (2)
C4—C3—H3B108.8C19—C18—H18120.4
H3A—C3—H3B107.7C17—C18—H18120.4
C3—C4—H4A109.5C18—C19—C20121.68 (19)
C3—C4—H4B109.5C18—C19—H19119.2
H4A—C4—H4B109.5C20—C19—H19119.2
C3—C4—H4C109.5C19—C20—C15117.2 (2)
H4A—C4—H4C109.5C19—C20—C21121.35 (18)
H4B—C4—H4C109.5C15—C20—C21121.4 (2)
O2—C5—C6116.87 (18)C26—C21—C22117.3 (2)
O2—C5—C10119.93 (19)C26—C21—C20121.94 (18)
C6—C5—C10123.2 (2)C22—C21—C20120.8 (2)
C5—C6—C7119.85 (19)C23—C22—C21121.2 (2)
C5—C6—H6120.1C23—C22—H22119.4
C7—C6—H6120.1C21—C22—H22119.4
N1—C7—C6121.63 (19)C22—C23—C24120.7 (2)
N1—C7—C8120.9 (2)C22—C23—H23119.6
C6—C7—C8117.5 (2)C24—C23—H23119.6
C9—C8—C7121.2 (2)C23—C24—C25119.3 (2)
C9—C8—H8119.4C23—C24—C27119.77 (19)
C7—C8—H8119.4C25—C24—C27120.9 (2)
C8—C9—C10122.0 (2)C26—C25—C24119.4 (2)
C8—C9—H9119.0C26—C25—H25120.3
C10—C9—H9119.0C24—C25—H25120.3
C11—C10—C9125.81 (19)C25—C26—C21122.1 (2)
C11—C10—C5117.9 (2)C25—C26—H26119.0
C9—C10—C5116.2 (2)C21—C26—H26119.0
C12—C11—C10122.29 (19)N2—C27—C24177.5 (3)
C7—N1—C2—C178.6 (3)C17—O3—C14—C12178.42 (18)
C3—N1—C2—C198.1 (2)C11—C12—C14—O4168.8 (3)
C7—N1—C3—C487.7 (3)C13—C12—C14—O411.6 (4)
C2—N1—C3—C488.9 (3)C11—C12—C14—O311.4 (3)
C13—O2—C5—C6178.28 (18)C13—C12—C14—O3168.26 (18)
C13—O2—C5—C101.8 (3)C20—C15—C16—C170.4 (4)
O2—C5—C6—C7179.15 (18)C15—C16—C17—C180.3 (4)
C10—C5—C6—C70.8 (3)C15—C16—C17—O3176.0 (2)
C2—N1—C7—C6177.0 (2)C14—O3—C17—C1668.9 (3)
C3—N1—C7—C60.5 (3)C14—O3—C17—C18114.7 (2)
C2—N1—C7—C83.6 (3)C16—C17—C18—C190.5 (4)
C3—N1—C7—C8179.86 (19)O3—C17—C18—C19176.0 (2)
C5—C6—C7—N1177.34 (19)C17—C18—C19—C200.1 (4)
C5—C6—C7—C82.1 (3)C18—C19—C20—C150.7 (4)
N1—C7—C8—C9177.9 (2)C18—C19—C20—C21177.7 (2)
C6—C7—C8—C91.6 (3)C16—C15—C20—C190.9 (4)
C7—C8—C9—C100.3 (3)C16—C15—C20—C21177.6 (2)
C8—C9—C10—C11179.9 (2)C19—C20—C21—C26159.0 (2)
C8—C9—C10—C51.6 (3)C15—C20—C21—C2622.6 (4)
O2—C5—C10—C110.3 (3)C19—C20—C21—C2222.7 (3)
C6—C5—C10—C11179.71 (19)C15—C20—C21—C22155.6 (2)
O2—C5—C10—C9179.01 (18)C26—C21—C22—C230.1 (3)
C6—C5—C10—C91.0 (3)C20—C21—C22—C23178.2 (2)
C9—C10—C11—C12179.0 (2)C21—C22—C23—C240.8 (4)
C5—C10—C11—C120.4 (3)C22—C23—C24—C251.4 (4)
C10—C11—C12—C131.8 (3)C22—C23—C24—C27178.6 (2)
C10—C11—C12—C14178.57 (19)C23—C24—C25—C261.0 (4)
C5—O2—C13—O1175.22 (18)C27—C24—C25—C26179.0 (2)
C5—O2—C13—C123.0 (3)C24—C25—C26—C210.1 (4)
C11—C12—C13—O1175.0 (2)C22—C21—C26—C250.5 (4)
C14—C12—C13—O14.7 (3)C20—C21—C26—C25177.8 (2)
C11—C12—C13—O23.0 (3)C23—C24—C27—N28 (6)
C14—C12—C13—O2177.36 (17)C25—C24—C27—N2172 (6)
C17—O3—C14—O41.7 (3)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C15–C20 ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.533.446 (3)170
C11—H11···N2ii0.932.593.435 (3)152
C16—H16···O1iii0.932.543.465 (3)177
C1—H1B···Cg3iv0.962.823.626 (3)142
Symmetry codes: (i) x+1, y+2, z+2; (ii) x1, y+2, z+1; (iii) x, y+2, z+2; (iv) x+1, y1, z.

Experimental details

Crystal data
Chemical formulaC27H22N2O4
Mr438.47
Crystal system, space groupTriclinic, P1
Temperature (K)300
a, b, c (Å)9.652 (3), 10.252 (4), 11.121 (4)
α, β, γ (°)87.214 (10), 86.358 (10), 84.348 (11)
V3)1091.9 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.24 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.979, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
10667, 3783, 2495
Rint0.048
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.173, 0.97
No. of reflections3783
No. of parameters301
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.37

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C15–C20 ring.
D—H···AD—HH···AD···AD—H···A
C6—H6···O1i0.932.533.446 (3)170
C11—H11···N2ii0.932.593.435 (3)152
C16—H16···O1iii0.932.543.465 (3)177
C1—H1B···Cg3iv0.962.823.626 (3)142
Symmetry codes: (i) x+1, y+2, z+2; (ii) x1, y+2, z+1; (iii) x, y+2, z+2; (iv) x+1, y1, z.
 

Acknowledgements

The authors thank Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for the data collection.

References

First citationBhat, M. A., Siddiqui, N. & Khan, S. A. (2006). Indian J. Pharm. Sci. 68, 120–124.  CAS
First citationBruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChimichi, S., Boccalini, M., Cosimelli, B., Viola, G., Vedaldi, D. & Dall Acqua, F. (2002). Tetrahedron Lett. 43, 7473–7476.  Web of Science CrossRef CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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