supplementary materials


bt6941 scheme

Acta Cryst. (2013). E69, o1746    [ doi:10.1107/S1600536813029905 ]

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

J. Kanchanadevi, G. Anbalagan, D. Kannan, M. Bakthadoss and V. Manivannan

Abstract top

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...[pi] interactions occur.

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 reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.133Δρmax = 0.41 e Å3
S = 1.03Δρmin = 0.18 e Å3
4154 reflectionsAbsolute structure: ?
300 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
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.
Acknowledgements top

none

references
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