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

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ISSN: 2056-9890

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

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, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
*Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

(Received 21 October 2013; accepted 31 October 2013; online 6 November 2013)

In the title compound, C28H23N3O2, the pyrazole ring makes a dihedral angle of 16.90 (6)° with the phenyl ring to which it is attached. Both di­hydro­pyran rings exhibit half-chair conformations. Intramolecular C—H⋯O interactions generate S(6) and S(8) ring motifs. In the crystal, weak C—H⋯O and C—H⋯π interactions occur.

Related literature

For the biological activities 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 related structures see: Ponnusamy et al. (2013[Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267-o268.]); Kanchanadevi et al. (2013[Kanchanadevi, J., Anbalagan, G., Kannan, D., Gunasekaran, B., Manivannan, V. & Bakthadoss, N. (2013). Acta Cryst. E69, o1035.]).

[Scheme 1]

Experimental

Crystal data
  • C28H23N3O2

  • Mr = 433.49

  • Triclinic, [P \overline 1]

  • a = 9.021 (5) Å

  • b = 9.604 (5) Å

  • c = 15.254 (5) Å

  • α = 72.720 (5)°

  • β = 76.997 (5)°

  • γ = 63.875 (5)°

  • V = 1126.1 (9) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 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

  • 20066 measured reflections

  • 4154 independent reflections

  • 3085 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.133

  • S = 1.03

  • 4154 reflections

  • 300 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C6—H6⋯O1 0.93 2.37 2.952 (2) 120
C28—H28C⋯O2 0.96 2.47 3.310 (3) 146
C16—H16A⋯O2i 0.97 2.56 3.380 (2) 143
C20—H20⋯Cg1ii 0.96 2.86 3.567 (3) 134
Symmetry codes: (i) -x, -y, -z+2; (ii) x-1, y+1, 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


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 reported similar structures (Ponnusamy et al., 2013; Kanchanadevi et al., 2013). The pyrazole ring makes a dihedral angle of 16.90 (6) ° and 69.04 (6) °, respectively with two phenyl [C1—C6 and C9—C14] rings.

The molecular structure is stabilized by weak intramolecular C—H···N, C—H···O interactions and the crystal packing is controlled by weak intermolecular C—H···O and C—H···π interactions [C20—H20···Cg1ii; H20···cg1ii 2.863Å, C20—H20···Cg1ii 134°; Cg1 is the centroid of the ring defined by the atoms C1—C6; symmetry operator for generating equivalent atoms: (ii) -1 + x, 1 + y, z].

Related literature top

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

Experimental top

A mixture of (2E)-3-(2-methylphenyl)-2-(2-formylphenoxymethyl) prop-2-enenitrile (0.28 g, 1 mmol) and 3-methyl-1-phenyl-1H-pyrazol -5-one (0.17 g, 1 mmol) was placed in a round bottom flask and melted at 200 ° C for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethyl acetate and hexane mixture (1:49 ratio) which successfully provided the title product as colorless solid in 93% yield.

Refinement top

H atoms were positioned geometrically and refined using a 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 C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3. The methyl groups were allowed to rotate but not to tip.

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. The packing of the title compound, viewed down the a axis. Hydrogen bonds are shown as dashed lines.
16-Methyl-11-(2-methylphenyl)-14-phenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-2(7),3,5,13 (17),15-pentaene-10-carbonitrile top
Crystal data top
C28H23N3O2Z = 2
Mr = 433.49F(000) = 456
Triclinic, P1Dx = 1.278 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.021 (5) ÅCell parameters from 9100 reflections
b = 9.604 (5) Åθ = 2.4–25.4°
c = 15.254 (5) ŵ = 0.08 mm1
α = 72.720 (5)°T = 295 K
β = 76.997 (5)°Block, colourless
γ = 63.875 (5)°0.30 × 0.20 × 0.20 mm
V = 1126.1 (9) Å3
Data collection top
Bruker APEXII CCD
diffractometer
4154 independent reflections
Radiation source: fine-focus sealed tube3085 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 0 pixels mm-1θmax = 25.4°, θmin = 2.4°
ω and ϕ scansh = 1010
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1111
Tmin = 0.980, Tmax = 0.983l = 1818
20066 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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0709P)2 + 0.226P]
where P = (Fo2 + 2Fc2)/3
4154 reflections(Δ/σ)max = 0.003
300 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C28H23N3O2γ = 63.875 (5)°
Mr = 433.49V = 1126.1 (9) Å3
Triclinic, P1Z = 2
a = 9.021 (5) ÅMo Kα radiation
b = 9.604 (5) ŵ = 0.08 mm1
c = 15.254 (5) ÅT = 295 K
α = 72.720 (5)°0.30 × 0.20 × 0.20 mm
β = 76.997 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
4154 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3085 reflections with I > 2σ(I)
Tmin = 0.980, Tmax = 0.983Rint = 0.034
20066 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.03Δρmax = 0.41 e Å3
4154 reflectionsΔρmin = 0.18 e Å3
300 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6925 (2)0.0765 (2)0.56488 (12)0.0419 (4)
C20.8398 (3)0.0745 (3)0.51420 (15)0.0625 (6)
H20.87880.00180.51800.075*
C30.9283 (3)0.1800 (3)0.45841 (16)0.0732 (7)
H31.02790.17910.42500.088*
C40.8716 (3)0.2860 (3)0.45144 (15)0.0688 (6)
H40.93240.35770.41380.083*
C50.7238 (3)0.2861 (3)0.50042 (14)0.0614 (6)
H50.68400.35720.49510.074*
C60.6334 (2)0.1812 (2)0.55777 (13)0.0491 (5)
H60.53370.18200.59100.059*
C70.4881 (2)0.0363 (2)0.69459 (11)0.0364 (4)
C80.28622 (19)0.0390 (2)0.79451 (11)0.0349 (4)
H80.19180.04270.76180.042*
C90.2496 (2)0.1847 (2)0.83666 (11)0.0363 (4)
C100.3741 (2)0.3256 (2)0.87619 (13)0.0441 (4)
H100.48010.32930.87230.053*
C110.3442 (3)0.4593 (2)0.92089 (13)0.0507 (5)
H110.42930.55270.94630.061*
C120.1869 (3)0.4537 (2)0.92762 (13)0.0519 (5)
H120.16400.54210.95980.062*
C130.0645 (2)0.3173 (2)0.88667 (13)0.0493 (5)
H130.04040.31600.89030.059*
C140.0913 (2)0.1809 (2)0.83990 (12)0.0415 (4)
C150.31559 (19)0.03344 (19)0.86501 (11)0.0351 (4)
C160.1756 (2)0.0616 (2)0.94426 (12)0.0425 (4)
H16A0.17240.03960.97930.051*
H16B0.19760.10880.98540.051*
C170.0135 (2)0.3002 (2)0.84581 (12)0.0435 (4)
C180.1443 (2)0.4159 (3)0.82910 (15)0.0598 (6)
H180.23740.40080.86350.072*
C190.1631 (3)0.5517 (3)0.76227 (16)0.0664 (6)
H190.26890.62870.75090.080*
C200.0261 (3)0.5744 (2)0.71199 (15)0.0616 (6)
H200.03880.66700.66650.074*
C210.1304 (2)0.4599 (2)0.72885 (13)0.0488 (5)
H210.22260.47670.69440.059*
C220.1540 (2)0.3200 (2)0.79597 (12)0.0388 (4)
C230.3274 (2)0.19451 (19)0.81404 (11)0.0365 (4)
H230.37240.22630.85400.044*
C240.4482 (2)0.1651 (2)0.72960 (12)0.0386 (4)
C250.5545 (2)0.2371 (2)0.67479 (14)0.0475 (5)
C260.5733 (3)0.3799 (3)0.68336 (19)0.0751 (7)
H26A0.68590.36880.66320.113*
H26B0.54620.38830.74670.113*
H26C0.49990.47410.64570.113*
C270.4710 (2)0.0739 (2)0.90646 (12)0.0402 (4)
C280.0485 (2)0.0383 (3)0.79348 (15)0.0606 (6)
H28A0.14470.06200.80350.091*
H28B0.01530.01300.72840.091*
H28C0.07460.05100.81900.091*
N10.64918 (19)0.16067 (19)0.61013 (11)0.0513 (4)
N20.60710 (17)0.03354 (17)0.62256 (10)0.0422 (4)
N30.5899 (2)0.1541 (2)0.94037 (13)0.0589 (5)
O10.43131 (14)0.08065 (13)0.72675 (8)0.0395 (3)
O20.01940 (14)0.16371 (16)0.91092 (9)0.0495 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0371 (9)0.0432 (10)0.0369 (9)0.0118 (8)0.0005 (7)0.0076 (8)
C20.0514 (12)0.0729 (15)0.0632 (14)0.0294 (11)0.0194 (10)0.0275 (12)
C30.0598 (14)0.0866 (17)0.0643 (15)0.0265 (13)0.0232 (11)0.0311 (13)
C40.0696 (15)0.0742 (16)0.0488 (12)0.0129 (13)0.0042 (11)0.0275 (11)
C50.0709 (15)0.0600 (13)0.0532 (12)0.0212 (11)0.0067 (11)0.0209 (10)
C60.0444 (11)0.0536 (12)0.0445 (11)0.0166 (9)0.0011 (8)0.0117 (9)
C70.0306 (8)0.0361 (9)0.0403 (9)0.0156 (7)0.0010 (7)0.0058 (7)
C80.0275 (8)0.0383 (9)0.0359 (9)0.0132 (7)0.0016 (7)0.0081 (7)
C90.0366 (9)0.0412 (10)0.0344 (9)0.0197 (8)0.0016 (7)0.0109 (7)
C100.0400 (10)0.0418 (10)0.0521 (11)0.0182 (8)0.0041 (8)0.0106 (8)
C110.0577 (12)0.0386 (10)0.0553 (12)0.0197 (9)0.0070 (9)0.0086 (9)
C120.0688 (14)0.0495 (12)0.0483 (11)0.0383 (11)0.0032 (10)0.0104 (9)
C130.0516 (11)0.0625 (13)0.0480 (11)0.0372 (11)0.0039 (9)0.0171 (10)
C140.0411 (10)0.0519 (11)0.0384 (9)0.0252 (9)0.0000 (7)0.0128 (8)
C150.0301 (8)0.0373 (9)0.0364 (9)0.0130 (7)0.0023 (7)0.0081 (7)
C160.0382 (10)0.0479 (10)0.0391 (10)0.0161 (8)0.0009 (7)0.0108 (8)
C170.0371 (10)0.0483 (11)0.0419 (10)0.0122 (8)0.0021 (8)0.0154 (8)
C180.0355 (10)0.0707 (15)0.0603 (13)0.0067 (10)0.0023 (9)0.0221 (11)
C190.0480 (13)0.0658 (15)0.0627 (14)0.0032 (11)0.0133 (11)0.0186 (12)
C200.0655 (14)0.0455 (12)0.0531 (12)0.0026 (10)0.0127 (11)0.0085 (9)
C210.0504 (11)0.0427 (11)0.0465 (11)0.0125 (9)0.0033 (9)0.0120 (9)
C220.0380 (9)0.0386 (10)0.0391 (9)0.0115 (8)0.0027 (7)0.0151 (8)
C230.0324 (9)0.0377 (9)0.0408 (9)0.0142 (8)0.0021 (7)0.0120 (7)
C240.0325 (9)0.0379 (10)0.0446 (10)0.0153 (8)0.0011 (7)0.0100 (8)
C250.0408 (10)0.0448 (11)0.0582 (12)0.0222 (9)0.0047 (9)0.0129 (9)
C260.0767 (16)0.0669 (15)0.0984 (19)0.0493 (13)0.0190 (14)0.0309 (14)
C270.0385 (10)0.0411 (10)0.0435 (10)0.0179 (9)0.0030 (8)0.0111 (8)
C280.0456 (12)0.0736 (15)0.0664 (14)0.0299 (11)0.0131 (10)0.0066 (11)
N10.0452 (9)0.0505 (10)0.0600 (10)0.0278 (8)0.0125 (8)0.0148 (8)
N20.0373 (8)0.0423 (8)0.0448 (8)0.0190 (7)0.0083 (6)0.0114 (7)
N30.0509 (10)0.0516 (10)0.0744 (12)0.0159 (9)0.0222 (9)0.0108 (9)
O10.0375 (6)0.0400 (7)0.0420 (7)0.0194 (5)0.0074 (5)0.0133 (5)
O20.0323 (7)0.0569 (8)0.0525 (8)0.0161 (6)0.0036 (6)0.0118 (6)
Geometric parameters (Å, º) top
C1—C61.367 (3)C15—C161.528 (2)
C1—C21.384 (3)C15—C231.550 (2)
C1—N21.420 (2)C16—O21.420 (2)
C2—C31.372 (3)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C3—C41.363 (3)C17—O21.377 (2)
C3—H30.9300C17—C221.383 (3)
C4—C51.374 (3)C17—C181.389 (3)
C4—H40.9300C18—C191.364 (3)
C5—C61.387 (3)C18—H180.9300
C5—H50.9300C19—C201.369 (3)
C6—H60.9300C19—H190.9300
C7—N21.349 (2)C20—C211.378 (3)
C7—O11.354 (2)C20—H200.9300
C7—C241.363 (2)C21—C221.388 (3)
C8—O11.4550 (19)C21—H210.9300
C8—C91.502 (2)C22—C231.520 (2)
C8—C151.564 (2)C23—C241.497 (2)
C8—H80.9800C23—H230.9800
C9—C101.392 (3)C24—C251.406 (2)
C9—C141.403 (2)C25—N11.319 (2)
C10—C111.375 (3)C25—C261.500 (3)
C10—H100.9300C26—H26A0.9600
C11—C121.377 (3)C26—H26B0.9600
C11—H110.9300C26—H26C0.9600
C12—C131.370 (3)C27—N31.139 (2)
C12—H120.9300C28—H28A0.9600
C13—C141.389 (3)C28—H28B0.9600
C13—H130.9300C28—H28C0.9600
C14—C281.508 (3)N1—N21.382 (2)
C15—C271.472 (2)
C6—C1—C2120.00 (18)C15—C16—H16A109.4
C6—C1—N2122.32 (16)O2—C16—H16B109.4
C2—C1—N2117.68 (17)C15—C16—H16B109.4
C3—C2—C1120.0 (2)H16A—C16—H16B108.0
C3—C2—H2120.0O2—C17—C22123.01 (16)
C1—C2—H2120.0O2—C17—C18115.77 (17)
C4—C3—C2120.6 (2)C22—C17—C18121.14 (19)
C4—C3—H3119.7C19—C18—C17120.1 (2)
C2—C3—H3119.7C19—C18—H18119.9
C3—C4—C5119.5 (2)C17—C18—H18119.9
C3—C4—H4120.3C18—C19—C20120.0 (2)
C5—C4—H4120.3C18—C19—H19120.0
C4—C5—C6120.7 (2)C20—C19—H19120.0
C4—C5—H5119.7C19—C20—C21119.9 (2)
C6—C5—H5119.7C19—C20—H20120.1
C1—C6—C5119.27 (19)C21—C20—H20120.1
C1—C6—H6120.4C20—C21—C22121.67 (19)
C5—C6—H6120.4C20—C21—H21119.2
N2—C7—O1122.29 (15)C22—C21—H21119.2
N2—C7—C24109.30 (15)C17—C22—C21117.23 (17)
O1—C7—C24128.28 (15)C17—C22—C23121.57 (16)
O1—C8—C9107.74 (13)C21—C22—C23121.20 (16)
O1—C8—C15109.91 (13)C24—C23—C22115.21 (14)
C9—C8—C15114.90 (14)C24—C23—C15106.57 (13)
O1—C8—H8108.0C22—C23—C15108.94 (13)
C9—C8—H8108.0C24—C23—H23108.7
C15—C8—H8108.0C22—C23—H23108.7
C10—C9—C14119.09 (16)C15—C23—H23108.7
C10—C9—C8119.30 (15)C7—C24—C25103.93 (15)
C14—C9—C8121.58 (15)C7—C24—C23121.78 (15)
C11—C10—C9121.61 (17)C25—C24—C23134.00 (16)
C11—C10—H10119.2N1—C25—C24111.93 (16)
C9—C10—H10119.2N1—C25—C26119.44 (17)
C10—C11—C12119.34 (18)C24—C25—C26128.61 (18)
C10—C11—H11120.3C25—C26—H26A109.5
C12—C11—H11120.3C25—C26—H26B109.5
C13—C12—C11119.63 (18)H26A—C26—H26B109.5
C13—C12—H12120.2C25—C26—H26C109.5
C11—C12—H12120.2H26A—C26—H26C109.5
C12—C13—C14122.41 (17)H26B—C26—H26C109.5
C12—C13—H13118.8N3—C27—C15177.91 (19)
C14—C13—H13118.8C14—C28—H28A109.5
C13—C14—C9117.83 (17)C14—C28—H28B109.5
C13—C14—C28118.88 (16)H28A—C28—H28B109.5
C9—C14—C28123.28 (16)C14—C28—H28C109.5
C27—C15—C16107.11 (14)H28A—C28—H28C109.5
C27—C15—C23108.72 (13)H28B—C28—H28C109.5
C16—C15—C23108.72 (14)C25—N1—N2105.44 (14)
C27—C15—C8110.90 (14)C7—N2—N1109.38 (14)
C16—C15—C8112.16 (13)C7—N2—C1131.23 (15)
C23—C15—C8109.13 (14)N1—N2—C1119.35 (14)
O2—C16—C15111.34 (14)C7—O1—C8111.93 (12)
O2—C16—H16A109.4C17—O2—C16116.17 (13)
C6—C1—C2—C31.4 (3)C20—C21—C22—C23179.94 (17)
N2—C1—C2—C3179.1 (2)C17—C22—C23—C24139.64 (17)
C1—C2—C3—C40.8 (4)C21—C22—C23—C2440.7 (2)
C2—C3—C4—C50.4 (4)C17—C22—C23—C1520.0 (2)
C3—C4—C5—C61.0 (4)C21—C22—C23—C15160.35 (15)
C2—C1—C6—C50.9 (3)C27—C15—C23—C2471.73 (17)
N2—C1—C6—C5179.67 (17)C16—C15—C23—C24171.97 (13)
C4—C5—C6—C10.3 (3)C8—C15—C23—C2449.35 (16)
O1—C8—C9—C1054.68 (19)C27—C15—C23—C22163.39 (13)
C15—C8—C9—C1068.2 (2)C16—C15—C23—C2247.10 (17)
O1—C8—C9—C14127.45 (16)C8—C15—C23—C2275.53 (16)
C15—C8—C9—C14109.68 (17)N2—C7—C24—C251.34 (19)
C14—C9—C10—C112.2 (3)O1—C7—C24—C25174.53 (17)
C8—C9—C10—C11175.76 (16)N2—C7—C24—C23175.98 (15)
C9—C10—C11—C120.6 (3)O1—C7—C24—C230.1 (3)
C10—C11—C12—C132.6 (3)C22—C23—C24—C7101.70 (19)
C11—C12—C13—C141.7 (3)C15—C23—C24—C719.3 (2)
C12—C13—C14—C91.1 (3)C22—C23—C24—C2585.5 (2)
C12—C13—C14—C28177.50 (18)C15—C23—C24—C25153.51 (19)
C10—C9—C14—C133.0 (2)C7—C24—C25—N11.3 (2)
C8—C9—C14—C13174.90 (15)C23—C24—C25—N1174.98 (18)
C10—C9—C14—C28175.56 (17)C7—C24—C25—C26176.9 (2)
C8—C9—C14—C286.6 (3)C23—C24—C25—C263.3 (4)
O1—C8—C15—C2753.68 (18)C24—C25—N1—N20.8 (2)
C9—C8—C15—C2768.02 (18)C26—C25—N1—N2177.66 (18)
O1—C8—C15—C16173.39 (13)O1—C7—N2—N1175.21 (15)
C9—C8—C15—C1651.69 (19)C24—C7—N2—N10.96 (19)
O1—C8—C15—C2366.07 (16)O1—C7—N2—C12.1 (3)
C9—C8—C15—C23172.23 (13)C24—C7—N2—C1178.30 (17)
C27—C15—C16—O2179.60 (14)C25—N1—N2—C70.1 (2)
C23—C15—C16—O263.08 (17)C25—N1—N2—C1177.82 (16)
C8—C15—C16—O257.70 (19)C6—C1—N2—C718.8 (3)
O2—C17—C18—C19176.47 (18)C2—C1—N2—C7161.74 (19)
C22—C17—C18—C190.3 (3)C6—C1—N2—N1164.07 (17)
C17—C18—C19—C200.4 (3)C2—C1—N2—N115.4 (3)
C18—C19—C20—C210.2 (3)N2—C7—O1—C8170.88 (15)
C19—C20—C21—C220.2 (3)C24—C7—O1—C813.7 (2)
O2—C17—C22—C21176.57 (15)C9—C8—O1—C7171.15 (13)
C18—C17—C22—C210.0 (3)C15—C8—O1—C745.26 (17)
O2—C17—C22—C233.8 (3)C22—C17—O2—C1617.4 (2)
C18—C17—C22—C23179.67 (16)C18—C17—O2—C16165.84 (16)
C20—C21—C22—C170.3 (3)C15—C16—O2—C1747.30 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···N10.932.422.759 (3)102
C6—H6···O10.932.372.952 (2)120
C28—H28C···O20.962.473.310 (3)146
C16—H16A···O2i0.972.563.380 (2)143
C20—H20···Cg1ii0.962.863.567134
Symmetry codes: (i) x, y, z+2; (ii) x1, y+1, z.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C2—H2···N10.932.422.759 (3)101.5
C6—H6···O10.932.372.952 (2)120.1
C28—H28C···O20.962.473.310 (3)146.0
C16—H16A···O2i0.972.563.380 (2)142.5
C20—H20···Cg1ii0.962.863.567134
Symmetry codes: (i) x, y, z+2; (ii) x1, y+1, z.
 

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