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

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

doi:10.1107/S1600536813029905

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1746

doi:10.1107/S1600536813029905

Open

access

16-Methyl-11-(2-methylphenyl)-14-phenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.0^2,7.0^13,17]heptadeca-2(7),3,5,13(17),15-pentaene-10-carbonitrile

Jeevanandam Kanchanadevi,^a Gopalakrishnan Anbalagan,^b Damodharan Kannan,^c Manickam Bakthadoss ^c and Vadivelu Manivannan ^d ^*

^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.

CCDC reference: 969711

Related literature

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

Crystal data

C₂₈H₂₃N₃O₂
M_r = 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 ) T_min = 0.980, T_max = 0.983
20066 measured reflections
4154 independent reflections
3085 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.133
S = 1.03
4154 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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.

Supporting information

CCDC reference: 969711

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813029905/bt6941sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029905/bt6941Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029905/bt6941Isup3.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 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.

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

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	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[8.7.0.0^2,7.0^13,17]heptadeca-2(7),3,5,13 (17),15-pentaene-10-carbonitrile top

Crystal data top

C₂₈H₂₃N₃O₂	Z = 2
M_r = 433.49	F(000) = 456
Triclinic, P1	D_x = 1.278 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.021 (5) Å	Cell parameters from 9100 reflections
b = 9.604 (5) Å	θ = 2.4–25.4°
c = 15.254 (5) Å	µ = 0.08 mm⁻¹
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 tube	3085 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 0 pixels mm^-1	θ_max = 25.4°, θ_min = 2.4°
ω and ϕ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.980, T_max = 0.983	l = −18→18
20066 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0709P)² + 0.226P] where P = (F_o² + 2F_c²)/3
4154 reflections	(Δ/σ)_max = 0.003
300 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₂₃N₃O₂	γ = 63.875 (5)°
M_r = 433.49	V = 1126.1 (9) Å³
Triclinic, P1	Z = 2
a = 9.021 (5) Å	Mo Kα radiation
b = 9.604 (5) Å	µ = 0.08 mm⁻¹
c = 15.254 (5) Å	T = 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)
T_min = 0.980, T_max = 0.983	R_int = 0.034
20066 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
4154 reflections	Δρ_min = −0.18 e Å⁻³
300 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.6925 (2)	−0.0765 (2)	0.56488 (12)	0.0419 (4)
C2	0.8398 (3)	−0.0745 (3)	0.51420 (15)	0.0625 (6)
H2	0.8788	−0.0018	0.5180	0.075*
C3	0.9283 (3)	−0.1800 (3)	0.45841 (16)	0.0732 (7)
H3	1.0279	−0.1791	0.4250	0.088*
C4	0.8716 (3)	−0.2860 (3)	0.45144 (15)	0.0688 (6)
H4	0.9324	−0.3577	0.4138	0.083*
C5	0.7238 (3)	−0.2861 (3)	0.50042 (14)	0.0614 (6)
H5	0.6840	−0.3572	0.4951	0.074*
C6	0.6334 (2)	−0.1812 (2)	0.55777 (13)	0.0491 (5)
H6	0.5337	−0.1820	0.5910	0.059*
C7	0.4881 (2)	0.0363 (2)	0.69459 (11)	0.0364 (4)
C8	0.28622 (19)	−0.0390 (2)	0.79451 (11)	0.0349 (4)
H8	0.1918	0.0427	0.7618	0.042*
C9	0.2496 (2)	−0.1847 (2)	0.83666 (11)	0.0363 (4)
C10	0.3741 (2)	−0.3256 (2)	0.87619 (13)	0.0441 (4)
H10	0.4801	−0.3293	0.8723	0.053*
C11	0.3442 (3)	−0.4593 (2)	0.92089 (13)	0.0507 (5)
H11	0.4293	−0.5527	0.9463	0.061*
C12	0.1869 (3)	−0.4537 (2)	0.92762 (13)	0.0519 (5)
H12	0.1640	−0.5421	0.9598	0.062*
C13	0.0645 (2)	−0.3173 (2)	0.88667 (13)	0.0493 (5)
H13	−0.0404	−0.3160	0.8903	0.059*
C14	0.0913 (2)	−0.1809 (2)	0.83990 (12)	0.0415 (4)
C15	0.31559 (19)	0.03344 (19)	0.86501 (11)	0.0351 (4)
C16	0.1756 (2)	0.0616 (2)	0.94426 (12)	0.0425 (4)
H16A	0.1724	−0.0396	0.9793	0.051*
H16B	0.1976	0.1088	0.9854	0.051*
C17	0.0135 (2)	0.3002 (2)	0.84581 (12)	0.0435 (4)
C18	−0.1443 (2)	0.4159 (3)	0.82910 (15)	0.0598 (6)
H18	−0.2374	0.4008	0.8635	0.072*
C19	−0.1631 (3)	0.5517 (3)	0.76227 (16)	0.0664 (6)
H19	−0.2689	0.6287	0.7509	0.080*
C20	−0.0261 (3)	0.5744 (2)	0.71199 (15)	0.0616 (6)
H20	−0.0388	0.6670	0.6665	0.074*
C21	0.1304 (2)	0.4599 (2)	0.72885 (13)	0.0488 (5)
H21	0.2226	0.4767	0.6944	0.059*
C22	0.1540 (2)	0.3200 (2)	0.79597 (12)	0.0388 (4)
C23	0.3274 (2)	0.19451 (19)	0.81404 (11)	0.0365 (4)
H23	0.3724	0.2263	0.8540	0.044*
C24	0.4482 (2)	0.1651 (2)	0.72960 (12)	0.0386 (4)
C25	0.5545 (2)	0.2371 (2)	0.67479 (14)	0.0475 (5)
C26	0.5733 (3)	0.3799 (3)	0.68336 (19)	0.0751 (7)
H26A	0.6859	0.3688	0.6632	0.113*
H26B	0.5462	0.3883	0.7467	0.113*
H26C	0.4999	0.4741	0.6457	0.113*
C27	0.4710 (2)	−0.0739 (2)	0.90646 (12)	0.0402 (4)
C28	−0.0485 (2)	−0.0383 (3)	0.79348 (15)	0.0606 (6)
H28A	−0.1447	−0.0620	0.8035	0.091*
H28B	−0.0153	−0.0130	0.7284	0.091*
H28C	−0.0746	0.0510	0.8190	0.091*
N1	0.64918 (19)	0.16067 (19)	0.61013 (11)	0.0513 (4)
N2	0.60710 (17)	0.03354 (17)	0.62256 (10)	0.0422 (4)
N3	0.5899 (2)	−0.1541 (2)	0.94037 (13)	0.0589 (5)
O1	0.43131 (14)	−0.08065 (13)	0.72675 (8)	0.0395 (3)
O2	0.01940 (14)	0.16371 (16)	0.91092 (9)	0.0495 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0371 (9)	0.0432 (10)	0.0369 (9)	−0.0118 (8)	0.0005 (7)	−0.0076 (8)
C2	0.0514 (12)	0.0729 (15)	0.0632 (14)	−0.0294 (11)	0.0194 (10)	−0.0275 (12)
C3	0.0598 (14)	0.0866 (17)	0.0643 (15)	−0.0265 (13)	0.0232 (11)	−0.0311 (13)
C4	0.0696 (15)	0.0742 (16)	0.0488 (12)	−0.0129 (13)	0.0042 (11)	−0.0275 (11)
C5	0.0709 (15)	0.0600 (13)	0.0532 (12)	−0.0212 (11)	−0.0067 (11)	−0.0209 (10)
C6	0.0444 (11)	0.0536 (12)	0.0445 (11)	−0.0166 (9)	−0.0011 (8)	−0.0117 (9)
C7	0.0306 (8)	0.0361 (9)	0.0403 (9)	−0.0156 (7)	0.0010 (7)	−0.0058 (7)
C8	0.0275 (8)	0.0383 (9)	0.0359 (9)	−0.0132 (7)	0.0016 (7)	−0.0081 (7)
C9	0.0366 (9)	0.0412 (10)	0.0344 (9)	−0.0197 (8)	0.0016 (7)	−0.0109 (7)
C10	0.0400 (10)	0.0418 (10)	0.0521 (11)	−0.0182 (8)	−0.0041 (8)	−0.0106 (8)
C11	0.0577 (12)	0.0386 (10)	0.0553 (12)	−0.0197 (9)	−0.0070 (9)	−0.0086 (9)
C12	0.0688 (14)	0.0495 (12)	0.0483 (11)	−0.0383 (11)	0.0032 (10)	−0.0104 (9)
C13	0.0516 (11)	0.0625 (13)	0.0480 (11)	−0.0372 (11)	0.0039 (9)	−0.0171 (10)
C14	0.0411 (10)	0.0519 (11)	0.0384 (9)	−0.0252 (9)	0.0000 (7)	−0.0128 (8)
C15	0.0301 (8)	0.0373 (9)	0.0364 (9)	−0.0130 (7)	−0.0023 (7)	−0.0081 (7)
C16	0.0382 (10)	0.0479 (10)	0.0391 (10)	−0.0161 (8)	−0.0009 (7)	−0.0108 (8)
C17	0.0371 (10)	0.0483 (11)	0.0419 (10)	−0.0122 (8)	−0.0021 (8)	−0.0154 (8)
C18	0.0355 (10)	0.0707 (15)	0.0603 (13)	−0.0067 (10)	−0.0023 (9)	−0.0221 (11)
C19	0.0480 (13)	0.0658 (15)	0.0627 (14)	0.0032 (11)	−0.0133 (11)	−0.0186 (12)
C20	0.0655 (14)	0.0455 (12)	0.0531 (12)	−0.0026 (10)	−0.0127 (11)	−0.0085 (9)
C21	0.0504 (11)	0.0427 (11)	0.0465 (11)	−0.0125 (9)	−0.0033 (9)	−0.0120 (9)
C22	0.0380 (9)	0.0386 (10)	0.0391 (9)	−0.0115 (8)	−0.0027 (7)	−0.0151 (8)
C23	0.0324 (9)	0.0377 (9)	0.0408 (9)	−0.0142 (8)	−0.0021 (7)	−0.0120 (7)
C24	0.0325 (9)	0.0379 (10)	0.0446 (10)	−0.0153 (8)	0.0011 (7)	−0.0100 (8)
C25	0.0408 (10)	0.0448 (11)	0.0582 (12)	−0.0222 (9)	0.0047 (9)	−0.0129 (9)
C26	0.0767 (16)	0.0669 (15)	0.0984 (19)	−0.0493 (13)	0.0190 (14)	−0.0309 (14)
C27	0.0385 (10)	0.0411 (10)	0.0435 (10)	−0.0179 (9)	−0.0030 (8)	−0.0111 (8)
C28	0.0456 (12)	0.0736 (15)	0.0664 (14)	−0.0299 (11)	−0.0131 (10)	−0.0066 (11)
N1	0.0452 (9)	0.0505 (10)	0.0600 (10)	−0.0278 (8)	0.0125 (8)	−0.0148 (8)
N2	0.0373 (8)	0.0423 (8)	0.0448 (8)	−0.0190 (7)	0.0083 (6)	−0.0114 (7)
N3	0.0509 (10)	0.0516 (10)	0.0744 (12)	−0.0159 (9)	−0.0222 (9)	−0.0108 (9)
O1	0.0375 (6)	0.0400 (7)	0.0420 (7)	−0.0194 (5)	0.0074 (5)	−0.0133 (5)
O2	0.0323 (7)	0.0569 (8)	0.0525 (8)	−0.0161 (6)	0.0036 (6)	−0.0118 (6)

Geometric parameters (Å, º) top

C1—C6	1.367 (3)	C15—C16	1.528 (2)
C1—C2	1.384 (3)	C15—C23	1.550 (2)
C1—N2	1.420 (2)	C16—O2	1.420 (2)
C2—C3	1.372 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.363 (3)	C17—O2	1.377 (2)
C3—H3	0.9300	C17—C22	1.383 (3)
C4—C5	1.374 (3)	C17—C18	1.389 (3)
C4—H4	0.9300	C18—C19	1.364 (3)
C5—C6	1.387 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.369 (3)
C6—H6	0.9300	C19—H19	0.9300
C7—N2	1.349 (2)	C20—C21	1.378 (3)
C7—O1	1.354 (2)	C20—H20	0.9300
C7—C24	1.363 (2)	C21—C22	1.388 (3)
C8—O1	1.4550 (19)	C21—H21	0.9300
C8—C9	1.502 (2)	C22—C23	1.520 (2)
C8—C15	1.564 (2)	C23—C24	1.497 (2)
C8—H8	0.9800	C23—H23	0.9800
C9—C10	1.392 (3)	C24—C25	1.406 (2)
C9—C14	1.403 (2)	C25—N1	1.319 (2)
C10—C11	1.375 (3)	C25—C26	1.500 (3)
C10—H10	0.9300	C26—H26A	0.9600
C11—C12	1.377 (3)	C26—H26B	0.9600
C11—H11	0.9300	C26—H26C	0.9600
C12—C13	1.370 (3)	C27—N3	1.139 (2)
C12—H12	0.9300	C28—H28A	0.9600
C13—C14	1.389 (3)	C28—H28B	0.9600
C13—H13	0.9300	C28—H28C	0.9600
C14—C28	1.508 (3)	N1—N2	1.382 (2)
C15—C27	1.472 (2)

C6—C1—C2	120.00 (18)	C15—C16—H16A	109.4
C6—C1—N2	122.32 (16)	O2—C16—H16B	109.4
C2—C1—N2	117.68 (17)	C15—C16—H16B	109.4
C3—C2—C1	120.0 (2)	H16A—C16—H16B	108.0
C3—C2—H2	120.0	O2—C17—C22	123.01 (16)
C1—C2—H2	120.0	O2—C17—C18	115.77 (17)
C4—C3—C2	120.6 (2)	C22—C17—C18	121.14 (19)
C4—C3—H3	119.7	C19—C18—C17	120.1 (2)
C2—C3—H3	119.7	C19—C18—H18	119.9
C3—C4—C5	119.5 (2)	C17—C18—H18	119.9
C3—C4—H4	120.3	C18—C19—C20	120.0 (2)
C5—C4—H4	120.3	C18—C19—H19	120.0
C4—C5—C6	120.7 (2)	C20—C19—H19	120.0
C4—C5—H5	119.7	C19—C20—C21	119.9 (2)
C6—C5—H5	119.7	C19—C20—H20	120.1
C1—C6—C5	119.27 (19)	C21—C20—H20	120.1
C1—C6—H6	120.4	C20—C21—C22	121.67 (19)
C5—C6—H6	120.4	C20—C21—H21	119.2
N2—C7—O1	122.29 (15)	C22—C21—H21	119.2
N2—C7—C24	109.30 (15)	C17—C22—C21	117.23 (17)
O1—C7—C24	128.28 (15)	C17—C22—C23	121.57 (16)
O1—C8—C9	107.74 (13)	C21—C22—C23	121.20 (16)
O1—C8—C15	109.91 (13)	C24—C23—C22	115.21 (14)
C9—C8—C15	114.90 (14)	C24—C23—C15	106.57 (13)
O1—C8—H8	108.0	C22—C23—C15	108.94 (13)
C9—C8—H8	108.0	C24—C23—H23	108.7
C15—C8—H8	108.0	C22—C23—H23	108.7
C10—C9—C14	119.09 (16)	C15—C23—H23	108.7
C10—C9—C8	119.30 (15)	C7—C24—C25	103.93 (15)
C14—C9—C8	121.58 (15)	C7—C24—C23	121.78 (15)
C11—C10—C9	121.61 (17)	C25—C24—C23	134.00 (16)
C11—C10—H10	119.2	N1—C25—C24	111.93 (16)
C9—C10—H10	119.2	N1—C25—C26	119.44 (17)
C10—C11—C12	119.34 (18)	C24—C25—C26	128.61 (18)
C10—C11—H11	120.3	C25—C26—H26A	109.5
C12—C11—H11	120.3	C25—C26—H26B	109.5
C13—C12—C11	119.63 (18)	H26A—C26—H26B	109.5
C13—C12—H12	120.2	C25—C26—H26C	109.5
C11—C12—H12	120.2	H26A—C26—H26C	109.5
C12—C13—C14	122.41 (17)	H26B—C26—H26C	109.5
C12—C13—H13	118.8	N3—C27—C15	177.91 (19)
C14—C13—H13	118.8	C14—C28—H28A	109.5
C13—C14—C9	117.83 (17)	C14—C28—H28B	109.5
C13—C14—C28	118.88 (16)	H28A—C28—H28B	109.5
C9—C14—C28	123.28 (16)	C14—C28—H28C	109.5
C27—C15—C16	107.11 (14)	H28A—C28—H28C	109.5
C27—C15—C23	108.72 (13)	H28B—C28—H28C	109.5
C16—C15—C23	108.72 (14)	C25—N1—N2	105.44 (14)
C27—C15—C8	110.90 (14)	C7—N2—N1	109.38 (14)
C16—C15—C8	112.16 (13)	C7—N2—C1	131.23 (15)
C23—C15—C8	109.13 (14)	N1—N2—C1	119.35 (14)
O2—C16—C15	111.34 (14)	C7—O1—C8	111.93 (12)
O2—C16—H16A	109.4	C17—O2—C16	116.17 (13)

C6—C1—C2—C3	−1.4 (3)	C20—C21—C22—C23	−179.94 (17)
N2—C1—C2—C3	179.1 (2)	C17—C22—C23—C24	139.64 (17)
C1—C2—C3—C4	0.8 (4)	C21—C22—C23—C24	−40.7 (2)
C2—C3—C4—C5	0.4 (4)	C17—C22—C23—C15	20.0 (2)
C3—C4—C5—C6	−1.0 (4)	C21—C22—C23—C15	−160.35 (15)
C2—C1—C6—C5	0.9 (3)	C27—C15—C23—C24	71.73 (17)
N2—C1—C6—C5	−179.67 (17)	C16—C15—C23—C24	−171.97 (13)
C4—C5—C6—C1	0.3 (3)	C8—C15—C23—C24	−49.35 (16)
O1—C8—C9—C10	54.68 (19)	C27—C15—C23—C22	−163.39 (13)
C15—C8—C9—C10	−68.2 (2)	C16—C15—C23—C22	−47.10 (17)
O1—C8—C9—C14	−127.45 (16)	C8—C15—C23—C22	75.53 (16)
C15—C8—C9—C14	109.68 (17)	N2—C7—C24—C25	−1.34 (19)
C14—C9—C10—C11	−2.2 (3)	O1—C7—C24—C25	174.53 (17)
C8—C9—C10—C11	175.76 (16)	N2—C7—C24—C23	−175.98 (15)
C9—C10—C11—C12	−0.6 (3)	O1—C7—C24—C23	−0.1 (3)
C10—C11—C12—C13	2.6 (3)	C22—C23—C24—C7	−101.70 (19)
C11—C12—C13—C14	−1.7 (3)	C15—C23—C24—C7	19.3 (2)
C12—C13—C14—C9	−1.1 (3)	C22—C23—C24—C25	85.5 (2)
C12—C13—C14—C28	177.50 (18)	C15—C23—C24—C25	−153.51 (19)
C10—C9—C14—C13	3.0 (2)	C7—C24—C25—N1	1.3 (2)
C8—C9—C14—C13	−174.90 (15)	C23—C24—C25—N1	174.98 (18)
C10—C9—C14—C28	−175.56 (17)	C7—C24—C25—C26	−176.9 (2)
C8—C9—C14—C28	6.6 (3)	C23—C24—C25—C26	−3.3 (4)
O1—C8—C15—C27	−53.68 (18)	C24—C25—N1—N2	−0.8 (2)
C9—C8—C15—C27	68.02 (18)	C26—C25—N1—N2	177.66 (18)
O1—C8—C15—C16	−173.39 (13)	O1—C7—N2—N1	−175.21 (15)
C9—C8—C15—C16	−51.69 (19)	C24—C7—N2—N1	0.96 (19)
O1—C8—C15—C23	66.07 (16)	O1—C7—N2—C1	2.1 (3)
C9—C8—C15—C23	−172.23 (13)	C24—C7—N2—C1	178.30 (17)
C27—C15—C16—O2	−179.60 (14)	C25—N1—N2—C7	−0.1 (2)
C23—C15—C16—O2	63.08 (17)	C25—N1—N2—C1	−177.82 (16)
C8—C15—C16—O2	−57.70 (19)	C6—C1—N2—C7	18.8 (3)
O2—C17—C18—C19	−176.47 (18)	C2—C1—N2—C7	−161.74 (19)
C22—C17—C18—C19	0.3 (3)	C6—C1—N2—N1	−164.07 (17)
C17—C18—C19—C20	−0.4 (3)	C2—C1—N2—N1	15.4 (3)
C18—C19—C20—C21	0.2 (3)	N2—C7—O1—C8	−170.88 (15)
C19—C20—C21—C22	0.2 (3)	C24—C7—O1—C8	13.7 (2)
O2—C17—C22—C21	176.57 (15)	C9—C8—O1—C7	−171.15 (13)
C18—C17—C22—C21	0.0 (3)	C15—C8—O1—C7	−45.26 (17)
O2—C17—C22—C23	−3.8 (3)	C22—C17—O2—C16	17.4 (2)
C18—C17—C22—C23	179.67 (16)	C18—C17—O2—C16	−165.84 (16)
C20—C21—C22—C17	−0.3 (3)	C15—C16—O2—C17	−47.30 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.93	2.42	2.759 (3)	102
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	134

Symmetry codes: (i) −x, −y, −z+2; (ii) x−1, y+1, z.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N1	0.93	2.42	2.759 (3)	101.5
C6—H6···O1	0.93	2.37	2.952 (2)	120.1
C28—H28C···O2	0.96	2.47	3.310 (3)	146.0
C16—H16A···O2ⁱ	0.97	2.56	3.380 (2)	142.5
C20—H20···Cg1ⁱⁱ	0.96	2.86	3.567	134

Symmetry codes: (i) −x, −y, −z+2; (ii) x−1, y+1, z.

References

Brooks, G. T. (1998). Pestic. Sci. 22, 41–50. CrossRef Web of Science Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627–2644. Web of Science PubMed CAS Google Scholar
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91–126. Budapest: Akademiai Kiado. Google Scholar
Kanchanadevi, J., Anbalagan, G., Kannan, D., Gunasekaran, B., Manivannan, V. & Bakthadoss, N. (2013). Acta Cryst. E69, o1035. CSD CrossRef IUCr Journals Google Scholar
Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267–o268. CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, 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
Valenti, 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

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1746

doi:10.1107/S1600536813029905

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

16-Methyl-11-(2-methylphenyl)-14-phenyl-8,12-dioxa-14,15-diazatetracyclo[8.7.0.0^2,7.0^13,17]heptadeca-2(7),3,5,13(17),15-pentaene-10-carbonitrile