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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 69| Part 7| July 2013| Page o1035
https://doi.org/10.1107/S1600536813015213

Methyl 11,14,16-tri­phenyl-8,12-dioxa-14,15-di­aza­tetra­cyclo­[8.7.0.02,7.013,17]hepta­deca-2(7),3,5,13(17),15-penta­ene-10-carboxyl­ate

J. Kanchanadevi,a G. Anbalagan,b D. Kannan,c B. Gunasekaran,d V. Manivannane* and N. Bakthadossf

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India, eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, and fDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 28 May 2013; accepted 1 June 2013; online 8 June 2013)

In the title compound, C33H26N2O4, the pyrazole ring makes dihedral angles of 15.13 (7) and 60.80 (7)° with the adjacent phenyl rings. Both di­hydro­pyran rings exhibit half-chair conformations. A weak intra­molecular C—H⋯O inter­action occurs. In the crystal, mol­ecules are linked into inversion dimers through pairs of C—H⋯N inter­actions. Weak C—H⋯π inter­actions are also observed.

Related literature

For the biological activity of 4H-chromenes, see: Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); Gabor (1988[Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.]); Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Valenti et al. (1993[Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.]); Tang et al. (2007[Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.]). For a related structure, see: Ponnusamy et al. (2013[Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267-o268.]).

[Scheme 1]

Experimental

Crystal data

  • C33H26N2O4

  • Mr = 514.56

  • Monoclinic, P 21 /n

  • a = 11.916 (5) Å

  • b = 10.876 (5) Å

  • c = 21.153 (5) Å

  • β = 105.797 (5)°

  • V = 2637.9 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.980, Tmax = 0.983

  • 40448 measured reflections

  • 4605 independent reflections

  • 3289 reflections with I > 2σ(I)

  • Rint = 0.050
Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.129

  • S = 1.01

  • 4605 reflections

  • 354 parameters

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg4 and Cg6 are the centroids of the N1/N2/C7/C24/C25, C1–C6 and C17–C22 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C18—H18⋯N2i 0.93 2.62 3.517 (3) 163
C6—H6⋯O1 0.93 2.26 2.877 (2) 123
C13—H13⋯Cg6ii 0.93 2.98 3.904 (8) 174
C18—H18⋯Cg1i 0.93 2.88 3.720 (5) 150
C23—H23⋯Cg4iii 0.98 2.86 3.787 (6) 159
Symmetry codes: (i) -x, -y+1, -z; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 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: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015213/is5278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015213/is5278Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813015213/is5278Isup3.cml

checkCIF report


Comment top

4H-Chromenes and their derivatives exhibit various biological activities such as anti-viral, anti-fungal, anti-inflammatory, antidiabetic, anti-anaphylactic and anti-cancer (Cai et al., 2006; Gabor, 1988; Brooks, 1998; Valenti et al., 1993; Tang et al., 2007).

The geometric parameters of the title molecule (Fig. 1) agree well with a reported similar structure (Ponnusamy et al., 2013). The pyrazole ring makes dihedral angles of 15.13 (7) and 60.80 (7)°, respectively, with two phenyl (C1–C6) and (C26–C31) rings. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is controlled by weak intermolecular C—H···N and C—H···π interactions (Table 1).

Related literature top

For the biological activity of 4H-chromenes, see: Cai et al. (2006); Gabor (1988); Brooks (1998); Valenti et al. (1993); Tang et al. (2007). For a related structure, see: Ponnusamy et al. (2013).

Experimental top

A mixture of (E)-methyl-2-[(2-formylphenoxy)methyl]-3-phenylacrylate (0.296 g, 1 mmol) and 1,3-diphenyl-4,5-dihydro-1H-pyrazol-5-one (0.236 g, 1 mmol) was placed in a round bottom flask and melted at 180 °C for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided the title compound as colorless solid in 93% yield.

Refinement top

H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for methine, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for methylene, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl.

Structure description top

4H-Chromenes and their derivatives exhibit various biological activities such as anti-viral, anti-fungal, anti-inflammatory, antidiabetic, anti-anaphylactic and anti-cancer (Cai et al., 2006; Gabor, 1988; Brooks, 1998; Valenti et al., 1993; Tang et al., 2007).

The geometric parameters of the title molecule (Fig. 1) agree well with a reported similar structure (Ponnusamy et al., 2013). The pyrazole ring makes dihedral angles of 15.13 (7) and 60.80 (7)°, respectively, with two phenyl (C1–C6) and (C26–C31) rings. The molecular structure is stabilized by a weak intramolecular C—H···O interaction and the crystal packing is controlled by weak intermolecular C—H···N and C—H···π interactions (Table 1).

For the biological activity of 4H-chromenes, see: Cai et al. (2006); Gabor (1988); Brooks (1998); Valenti et al. (1993); Tang et al. (2007). For a related structure, see: Ponnusamy et al. (2013).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. A packing diagram of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
Methyl 11,14,16-triphenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-2(7),3,5,13(17),15-pentaene-10-carboxylate top
Crystal data top
C33H26N2O4F(000) = 1080
Mr = 514.56Dx = 1.296 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9160 reflections
a = 11.916 (5) Åθ = 2.3–25.1°
b = 10.876 (5) ŵ = 0.09 mm−1
c = 21.153 (5) ÅT = 295 K
β = 105.797 (5)°Block, colourless
V = 2637.9 (18) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		4605 independent reflections
Radiation source: fine-focus sealed tube3289 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 0 pixels mm-1θmax = 25.1°, θmin = 2.3°
ω and φ scansh = −14→14
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		k = −12→12
Tmin = 0.980, Tmax = 0.983l = −24→24
40448 measured reflections
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0765P)2 + 0.2117P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
4605 reflectionsΔρmax = 0.22 e Å−3
354 parametersΔρmin = −0.15 e Å−3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0055 (11)
Crystal data top
C33H26N2O4V = 2637.9 (18) Å3
Mr = 514.56Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.916 (5) ŵ = 0.09 mm−1
b = 10.876 (5) ÅT = 295 K
c = 21.153 (5) Å0.30 × 0.20 × 0.20 mm
β = 105.797 (5)°
Data collection top
Bruker APEXII CCD
diffractometer		4605 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3289 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.983Rint = 0.050
40448 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.01Δρmax = 0.22 e Å−3
4605 reflectionsΔρmin = −0.15 e Å−3
354 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.05478 (14)0.91979 (14)−0.10983 (8)0.0365 (4)
C2−0.00894 (17)0.91873 (17)−0.17503 (8)0.0485 (5)
H2−0.08650.8936−0.18680.058*
C30.0436 (2)0.9554 (2)−0.22240 (9)0.0640 (6)
H30.00080.9555−0.26630.077*
C40.1577 (2)0.9914 (2)−0.20573 (11)0.0709 (6)
H40.19291.0147−0.23810.085*
C50.21952 (19)0.9930 (2)−0.14101 (11)0.0678 (6)
H50.29701.0184−0.12950.081*
C60.16912 (16)0.95781 (18)−0.09264 (9)0.0525 (5)
H60.21190.9597−0.04870.063*
C70.04554 (14)0.84233 (14)0.00130 (8)0.0340 (4)
C80.18737 (14)0.83563 (15)0.10115 (8)0.0365 (4)
H80.15950.90840.11960.044*
C90.31735 (15)0.83154 (16)0.12662 (8)0.0414 (4)
C100.38724 (16)0.77182 (19)0.09357 (10)0.0559 (5)
H100.35320.73490.05320.067*
C110.50601 (18)0.7664 (2)0.11951 (13)0.0738 (7)
H110.55190.72680.09660.089*
C120.5564 (2)0.8188 (3)0.17848 (14)0.0864 (9)
H120.63650.81220.19680.104*
C130.4900 (2)0.8812 (3)0.21107 (12)0.0845 (8)
H130.52550.91910.25090.101*
C140.37027 (18)0.8886 (2)0.18530 (10)0.0611 (6)
H140.32560.93200.20760.073*
C150.12185 (14)0.72167 (14)0.11748 (7)0.0342 (4)
O20.08181 (11)0.50306 (10)0.08741 (7)0.0573 (4)
C17−0.02322 (16)0.51735 (15)0.09970 (8)0.0433 (4)
C18−0.07915 (18)0.40980 (18)0.10863 (9)0.0550 (5)
H18−0.04530.33420.10450.066*
C19−0.18357 (19)0.4139 (2)0.12349 (10)0.0625 (6)
H19−0.22160.34120.12830.075*
C20−0.23285 (18)0.5254 (2)0.13141 (10)0.0618 (6)
H20−0.30310.52850.14260.074*
C21−0.17688 (16)0.63237 (18)0.12258 (9)0.0518 (5)
H21−0.20990.70760.12830.062*
C22−0.07280 (14)0.63042 (15)0.10545 (8)0.0381 (4)
C23−0.01121 (14)0.74599 (14)0.09516 (8)0.0340 (4)
H23−0.02950.81070.12300.041*
C24−0.03910 (14)0.79328 (14)0.02535 (8)0.0332 (4)
C25−0.14127 (14)0.80602 (14)−0.02772 (8)0.0354 (4)
C26−0.26381 (14)0.77063 (16)−0.03464 (8)0.0393 (4)
C27−0.29485 (17)0.64951 (17)−0.03038 (9)0.0502 (5)
H27−0.23720.5894−0.01990.060*
C28−0.4097 (2)0.6165 (2)−0.04147 (11)0.0685 (6)
H28−0.42940.5342−0.03920.082*
C29−0.4949 (2)0.7035 (3)−0.05576 (13)0.0823 (8)
H29−0.57260.6809−0.06250.099*
C30−0.46592 (19)0.8242 (3)−0.06011 (13)0.0828 (8)
H30−0.52410.8838−0.07000.099*
C31−0.35080 (16)0.85816 (19)−0.04987 (10)0.0589 (6)
H31−0.33180.9404−0.05330.071*
C320.16275 (15)0.70167 (16)0.19162 (8)0.0397 (4)
C330.1692 (2)0.7890 (3)0.29487 (10)0.0889 (9)
H33A0.13940.71630.31030.133*
H33B0.14110.86040.31250.133*
H33C0.25290.78780.30890.133*
N1−0.11824 (12)0.85767 (12)−0.07964 (7)0.0383 (4)
N2−0.00009 (11)0.88050 (12)−0.06145 (6)0.0348 (3)
O10.16074 (9)0.85152 (10)0.03056 (5)0.0396 (3)
C160.14938 (15)0.60844 (15)0.08254 (9)0.0414 (4)
H16A0.13730.62800.03640.050*
H16B0.23120.58840.10050.050*
O30.21895 (13)0.61598 (12)0.21744 (6)0.0634 (4)
O40.13024 (12)0.79288 (12)0.22348 (6)0.0590 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0438 (10)0.0316 (9)0.0343 (9)0.0017 (7)0.0112 (7)0.0032 (7)
C20.0536 (12)0.0533 (11)0.0370 (10)−0.0019 (9)0.0097 (9)0.0021 (8)
C30.0802 (16)0.0792 (15)0.0332 (10)−0.0054 (12)0.0164 (10)0.0021 (10)
C40.0790 (16)0.0881 (17)0.0552 (14)−0.0065 (13)0.0346 (12)0.0133 (12)
C50.0556 (13)0.0908 (17)0.0597 (14)−0.0093 (12)0.0203 (11)0.0206 (12)
C60.0492 (12)0.0646 (12)0.0421 (11)−0.0050 (10)0.0097 (9)0.0119 (9)
C70.0345 (9)0.0336 (9)0.0306 (9)0.0014 (7)0.0034 (7)0.0014 (7)
C80.0398 (10)0.0387 (9)0.0286 (9)0.0014 (7)0.0052 (7)0.0016 (7)
C90.0392 (10)0.0453 (10)0.0355 (10)−0.0040 (8)0.0030 (8)0.0087 (8)
C100.0423 (11)0.0698 (13)0.0540 (12)−0.0001 (10)0.0104 (9)0.0010 (10)
C110.0376 (12)0.0990 (18)0.0830 (17)0.0050 (11)0.0135 (12)0.0177 (14)
C120.0410 (13)0.133 (2)0.0752 (18)−0.0137 (14)−0.0012 (13)0.0407 (17)
C130.0637 (16)0.128 (2)0.0460 (13)−0.0416 (15)−0.0112 (12)0.0112 (14)
C140.0566 (13)0.0784 (14)0.0430 (11)−0.0212 (11)0.0047 (10)−0.0017 (10)
C150.0365 (9)0.0359 (9)0.0287 (9)0.0023 (7)0.0064 (7)0.0017 (7)
O20.0600 (9)0.0364 (7)0.0816 (10)−0.0005 (6)0.0295 (8)−0.0085 (6)
C170.0499 (11)0.0406 (10)0.0369 (10)−0.0043 (8)0.0077 (8)0.0007 (8)
C180.0671 (14)0.0420 (11)0.0510 (12)−0.0099 (10)0.0078 (10)−0.0007 (9)
C190.0683 (15)0.0590 (14)0.0527 (13)−0.0229 (11)0.0038 (11)0.0119 (10)
C200.0508 (12)0.0781 (16)0.0574 (13)−0.0135 (11)0.0160 (10)0.0157 (11)
C210.0474 (12)0.0582 (12)0.0511 (12)−0.0007 (9)0.0155 (9)0.0119 (9)
C220.0400 (10)0.0412 (10)0.0304 (9)−0.0014 (7)0.0052 (7)0.0049 (7)
C230.0361 (9)0.0344 (9)0.0306 (9)0.0032 (7)0.0077 (7)0.0017 (7)
C240.0354 (9)0.0315 (8)0.0317 (9)0.0019 (7)0.0075 (7)0.0007 (7)
C250.0386 (10)0.0336 (9)0.0323 (9)−0.0001 (7)0.0067 (7)−0.0004 (7)
C260.0361 (10)0.0492 (11)0.0298 (9)−0.0017 (8)0.0045 (7)−0.0003 (7)
C270.0477 (12)0.0523 (11)0.0494 (12)−0.0088 (9)0.0113 (9)−0.0032 (9)
C280.0628 (15)0.0766 (15)0.0662 (15)−0.0275 (12)0.0177 (12)−0.0068 (12)
C290.0417 (13)0.124 (2)0.0783 (17)−0.0230 (15)0.0107 (12)−0.0044 (16)
C300.0375 (13)0.104 (2)0.099 (2)0.0145 (13)0.0047 (12)0.0103 (16)
C310.0408 (12)0.0642 (13)0.0651 (14)0.0062 (9)0.0032 (10)0.0074 (10)
C320.0392 (10)0.0408 (10)0.0370 (10)0.0023 (8)0.0066 (8)0.0043 (8)
C330.118 (2)0.113 (2)0.0290 (11)0.0323 (17)0.0092 (12)−0.0018 (12)
N10.0350 (8)0.0413 (8)0.0354 (8)−0.0010 (6)0.0044 (6)0.0021 (6)
N20.0343 (8)0.0374 (8)0.0305 (7)−0.0002 (6)0.0051 (6)0.0046 (6)
O10.0354 (7)0.0497 (7)0.0307 (6)−0.0011 (5)0.0039 (5)0.0076 (5)
C160.0434 (10)0.0387 (10)0.0429 (10)0.0022 (8)0.0132 (8)0.0009 (8)
O30.0791 (10)0.0559 (8)0.0451 (8)0.0196 (7)−0.0004 (7)0.0125 (6)
O40.0785 (10)0.0661 (9)0.0288 (7)0.0220 (7)0.0082 (6)−0.0019 (6)
Geometric parameters (Å, º) top
C1—C61.375 (2)C17—C181.384 (3)
C1—C21.382 (2)C18—C191.364 (3)
C1—N21.422 (2)C18—H180.9300
C2—C31.377 (3)C19—C201.378 (3)
C2—H20.9300C19—H190.9300
C3—C41.366 (3)C20—C211.379 (3)
C3—H30.9300C20—H200.9300
C4—C51.367 (3)C21—C221.384 (3)
C4—H40.9300C21—H210.9300
C5—C61.374 (3)C22—C231.501 (2)
C5—H50.9300C23—C241.513 (2)
C6—H60.9300C23—H230.9800
C7—O11.3472 (19)C24—C251.420 (2)
C7—N21.355 (2)C25—N11.327 (2)
C7—C241.356 (2)C25—C261.478 (2)
C8—O11.4500 (19)C26—C271.378 (2)
C8—C91.496 (2)C26—C311.379 (3)
C8—C151.553 (2)C27—C281.372 (3)
C8—H80.9800C27—H270.9300
C9—C141.377 (3)C28—C291.360 (3)
C9—C101.386 (3)C28—H280.9300
C10—C111.373 (3)C29—C301.368 (4)
C10—H100.9300C29—H290.9300
C11—C121.354 (4)C30—C311.380 (3)
C11—H110.9300C30—H300.9300
C12—C131.363 (4)C31—H310.9300
C12—H120.9300C32—O31.190 (2)
C13—C141.384 (3)C32—O41.315 (2)
C13—H130.9300C33—O41.455 (2)
C14—H140.9300C33—H33A0.9600
C15—C161.517 (2)C33—H33B0.9600
C15—C321.526 (2)C33—H33C0.9600
C15—C231.549 (2)N1—N21.3772 (19)
O2—C171.355 (2)C16—H16A0.9700
O2—C161.420 (2)C16—H16B0.9700
C17—C221.384 (2)
C6—C1—C2120.15 (16)C19—C20—C21119.2 (2)
C6—C1—N2121.12 (15)C19—C20—H20120.4
C2—C1—N2118.73 (15)C21—C20—H20120.4
C3—C2—C1119.27 (18)C20—C21—C22121.58 (19)
C3—C2—H2120.4C20—C21—H21119.2
C1—C2—H2120.4C22—C21—H21119.2
C4—C3—C2120.86 (19)C21—C22—C17118.11 (16)
C4—C3—H3119.6C21—C22—C23122.26 (16)
C2—C3—H3119.6C17—C22—C23119.60 (16)
C3—C4—C5119.3 (2)C22—C23—C24116.12 (13)
C3—C4—H4120.3C22—C23—C15108.25 (13)
C5—C4—H4120.3C24—C23—C15106.87 (13)
C4—C5—C6121.1 (2)C22—C23—H23108.5
C4—C5—H5119.5C24—C23—H23108.5
C6—C5—H5119.5C15—C23—H23108.5
C5—C6—C1119.30 (18)C7—C24—C25103.30 (14)
C5—C6—H6120.4C7—C24—C23120.77 (14)
C1—C6—H6120.4C25—C24—C23135.88 (15)
O1—C7—N2120.94 (14)N1—C25—C24111.68 (14)
O1—C7—C24128.72 (14)N1—C25—C26116.71 (14)
N2—C7—C24110.29 (14)C24—C25—C26131.59 (15)
O1—C8—C9106.82 (13)C27—C26—C31118.50 (17)
O1—C8—C15109.99 (12)C27—C26—C25121.20 (16)
C9—C8—C15115.48 (13)C31—C26—C25120.17 (16)
O1—C8—H8108.1C28—C27—C26120.8 (2)
C9—C8—H8108.1C28—C27—H27119.6
C15—C8—H8108.1C26—C27—H27119.6
C14—C9—C10118.36 (18)C29—C28—C27120.4 (2)
C14—C9—C8119.10 (17)C29—C28—H28119.8
C10—C9—C8122.54 (16)C27—C28—H28119.8
C11—C10—C9120.9 (2)C28—C29—C30119.7 (2)
C11—C10—H10119.5C28—C29—H29120.1
C9—C10—H10119.5C30—C29—H29120.1
C12—C11—C10120.0 (2)C29—C30—C31120.3 (2)
C12—C11—H11120.0C29—C30—H30119.8
C10—C11—H11120.0C31—C30—H30119.8
C11—C12—C13120.2 (2)C26—C31—C30120.3 (2)
C11—C12—H12119.9C26—C31—H31119.9
C13—C12—H12119.9C30—C31—H31119.9
C12—C13—C14120.5 (2)O3—C32—O4124.26 (16)
C12—C13—H13119.8O3—C32—C15124.45 (16)
C14—C13—H13119.8O4—C32—C15111.28 (14)
C9—C14—C13119.9 (2)O4—C33—H33A109.5
C9—C14—H14120.0O4—C33—H33B109.5
C13—C14—H14120.0H33A—C33—H33B109.5
C16—C15—C32109.52 (13)O4—C33—H33C109.5
C16—C15—C23109.22 (13)H33A—C33—H33C109.5
C32—C15—C23110.59 (13)H33B—C33—H33C109.5
C16—C15—C8110.55 (14)C25—N1—N2105.72 (12)
C32—C15—C8107.64 (13)C7—N2—N1109.00 (12)
C23—C15—C8109.31 (12)C7—N2—C1131.03 (14)
C17—O2—C16119.54 (13)N1—N2—C1119.23 (12)
O2—C17—C22123.89 (15)C7—O1—C8111.98 (12)
O2—C17—C18115.69 (16)O2—C16—C15114.68 (14)
C22—C17—C18120.38 (18)O2—C16—H16A108.6
C19—C18—C17120.47 (19)C15—C16—H16A108.6
C19—C18—H18119.8O2—C16—H16B108.6
C17—C18—H18119.8C15—C16—H16B108.6
C18—C19—C20120.14 (19)H16A—C16—H16B107.6
C18—C19—H19119.9C32—O4—C33117.05 (15)
C20—C19—H19119.9
C6—C1—C2—C30.4 (3)O1—C7—C24—C233.7 (3)
N2—C1—C2—C3−179.34 (17)N2—C7—C24—C23−178.75 (13)
C1—C2—C3—C40.6 (3)C22—C23—C24—C7−141.22 (16)
C2—C3—C4—C5−1.1 (4)C15—C23—C24—C7−20.34 (19)
C3—C4—C5—C60.6 (4)C22—C23—C24—C2541.6 (3)
C4—C5—C6—C10.3 (3)C15—C23—C24—C25162.47 (17)
C2—C1—C6—C5−0.9 (3)C7—C24—C25—N10.66 (18)
N2—C1—C6—C5178.87 (17)C23—C24—C25—N1178.18 (16)
O1—C8—C9—C14141.20 (16)C7—C24—C25—C26179.51 (17)
C15—C8—C9—C14−96.15 (19)C23—C24—C25—C26−3.0 (3)
O1—C8—C9—C10−39.1 (2)N1—C25—C26—C27116.90 (18)
C15—C8—C9—C1083.5 (2)C24—C25—C26—C27−61.9 (2)
C14—C9—C10—C111.9 (3)N1—C25—C26—C31−58.8 (2)
C8—C9—C10—C11−177.79 (18)C24—C25—C26—C31122.4 (2)
C9—C10—C11—C120.7 (3)C31—C26—C27—C280.4 (3)
C10—C11—C12—C13−2.6 (4)C25—C26—C27—C28−175.35 (18)
C11—C12—C13—C142.0 (4)C26—C27—C28—C29−1.2 (3)
C10—C9—C14—C13−2.5 (3)C27—C28—C29—C301.0 (4)
C8—C9—C14—C13177.18 (18)C28—C29—C30—C31−0.2 (4)
C12—C13—C14—C90.6 (4)C27—C26—C31—C300.4 (3)
O1—C8—C15—C1654.65 (17)C25—C26—C31—C30176.2 (2)
C9—C8—C15—C16−66.31 (18)C29—C30—C31—C26−0.5 (4)
O1—C8—C15—C32174.23 (12)C16—C15—C32—O37.7 (2)
C9—C8—C15—C3253.27 (18)C23—C15—C32—O3128.08 (18)
O1—C8—C15—C23−65.61 (16)C8—C15—C32—O3−112.56 (19)
C9—C8—C15—C23173.44 (13)C16—C15—C32—O4−173.82 (14)
C16—O2—C17—C222.7 (3)C23—C15—C32—O4−53.41 (18)
C16—O2—C17—C18−175.26 (15)C8—C15—C32—O465.95 (18)
O2—C17—C18—C19177.76 (17)C24—C25—N1—N2−0.31 (18)
C22—C17—C18—C19−0.3 (3)C26—C25—N1—N2−179.34 (13)
C17—C18—C19—C20−1.7 (3)O1—C7—N2—N1178.36 (13)
C18—C19—C20—C211.6 (3)C24—C7—N2—N10.63 (18)
C19—C20—C21—C220.5 (3)O1—C7—N2—C18.5 (3)
C20—C21—C22—C17−2.4 (3)C24—C7—N2—C1−169.21 (15)
C20—C21—C22—C23179.53 (16)C25—N1—N2—C7−0.18 (17)
O2—C17—C22—C21−175.60 (16)C25—N1—N2—C1171.04 (13)
C18—C17—C22—C212.3 (3)C6—C1—N2—C7−19.0 (3)
O2—C17—C22—C232.5 (3)C2—C1—N2—C7160.76 (16)
C18—C17—C22—C23−179.60 (16)C6—C1—N2—N1172.05 (15)
C21—C22—C23—C24−93.1 (2)C2—C1—N2—N1−8.2 (2)
C17—C22—C23—C2488.85 (18)N2—C7—O1—C8165.39 (14)
C21—C22—C23—C15146.77 (16)C24—C7—O1—C8−17.3 (2)
C17—C22—C23—C15−31.3 (2)C9—C8—O1—C7172.87 (13)
C16—C15—C23—C2253.54 (17)C15—C8—O1—C746.85 (17)
C32—C15—C23—C22−67.05 (16)C17—O2—C16—C1523.4 (2)
C8—C15—C23—C22174.61 (13)C32—C15—C16—O269.47 (18)
C16—C15—C23—C24−72.22 (16)C23—C15—C16—O2−51.78 (18)
C32—C15—C23—C24167.19 (13)C8—C15—C16—O2−172.09 (13)
C8—C15—C23—C2448.85 (16)O3—C32—O4—C331.9 (3)
O1—C7—C24—C25−178.27 (15)C15—C32—O4—C33−176.62 (18)
N2—C7—C24—C25−0.76 (17)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg4 and Cg6 are the centroids of the N1/N2/C7/C24/C25, C1–C6 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C18—H18···N2i0.932.623.517 (3)163
C6—H6···O10.932.262.877 (2)123
C13—H13···Cg6ii0.932.983.904 (8)174
C18—H18···Cg1i0.932.883.720 (5)150
C23—H23···Cg4iii0.982.863.787 (6)159
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC33H26N2O4
Mr514.56
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)11.916 (5), 10.876 (5), 21.153 (5)
β (°) 105.797 (5)
V (Å3)2637.9 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.980, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections		40448, 4605, 3289
Rint0.050
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.129, 1.01
No. of reflections4605
No. of parameters354
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.22, −0.15

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg4 and Cg6 are the centroids of the N1/N2/C7/C24/C25, C1–C6 and C17–C22 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C18—H18···N2i0.932.623.517 (3)163
C6—H6···O10.932.262.877 (2)123
C13—H13···Cg6ii0.932.983.904 (8)174
C18—H18···Cg1i0.932.883.720 (5)150
C23—H23···Cg4iii0.982.863.787 (6)159
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y+2, −z.
 

References

First citationBrooks, G. T. (1998). Pestic. Sci. 22, 41–50.  CrossRef Web of Science Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627–2644.  Web of Science PubMed CAS Google Scholar
 First citationGabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91–126. Budapest: Akademiai Kiado.  Google Scholar
 First citationPonnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267–o268.  CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437–o1438.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationValenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349–360.  CAS PubMed Web of Science Google Scholar

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ISSN: 2056-9890
Volume 69| Part 7| July 2013| Page o1035
https://doi.org/10.1107/S1600536813015213
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