(2S,5S,6R)-5-(4-Methyl­phen­yl)-3-phenyl-4,8-dioxa-3-aza­tricyclo­[7.4.0.02,6]trideca-1(13),9,11-triene-6-carbonitrile

Swaminathan, K.; Sethusankar, K.; Srinivasan, J.; Bakthadoss, M.

doi:10.1107/S1600536811055413

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o283-o284

doi:10.1107/S1600536811055413

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(2S,5S,6R)-5-(4-Methylphenyl)-3-phenyl-4,8-dioxa-3-azatricyclo[7.4.0.0^2,6]trideca-1(13),9,11-triene-6-carbonitrile

K. Swaminathan,^a K. Sethusankar,^a ^* J. Srinivasan ^b and M. Bakthadoss ^b

^aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 12 December 2011; accepted 23 December 2011; online 7 January 2012)

In the title compound, C₂₄H₂₀N₂O₂, the six-membered pyran ring adopts a half-chair conformation with one C atom deviating from the mean plane of the remaining ring atoms by 0.654 (6) Å. The five-membered isoxazole ring adopts an N-envelope conformation with the N atom displaced by 0.742 (5) Å from the mean plane formed by the remaining ring atoms. The carbonitrile side chain is almost linear, with a C—C—N angle of 178.6 (5)°. The crystal packing is stabilized by intermolecular C—H⋯N interactions, through bifurcated acceptor hydrogen bonds formed between the carbonitrile N atom and two alternate C atoms in the unsubstituted benzene ring. The molecular structure and crystal packing are further stabilized by intramolecular and intermolecular C—H⋯π interactions.

Related literature

For uses of benzopyran and isoxazolidine derivatives, see: Green et al. (1982 ); Kashiwada et al. (2001 ); Mullen et al. (1988 ). For a related structure, see: Swaminathan et al. (2011 ). For puckering parameters, see: Cremer & Pople (1975 ). For synthetic details, see: Bakthadoss & Murugan (2010 ).

Experimental

Crystal data

C₂₄H₂₀N₂O₂
M_r = 368.42
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.9890 (16) Å
b = 9.8432 (19) Å
c = 22.084 (4) Å
V = 1954.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.976, T_max = 0.980
10510 measured reflections
4476 independent reflections
2396 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.252
S = 1.00
4476 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19–C24 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1	0.93	2.99	3.701 (5)	134
C20—H20⋯Cg2ⁱ	0.93	2.95	3.803 (6)	153
C21—H21⋯N2ⁱⁱ	0.93	2.56	3.385 (6)	148
C23—H23⋯N2ⁱⁱⁱ	0.93	2.62	3.466 (7)	151
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055413/pv2496sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055413/pv2496Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055413/pv2496Isup3.cml

checkCIF report

Comment top

There has been a flurry of activity on the synthesis of benzopyran and isoxazolidine derivatives owing to their well established biological and pharmacological activities. For example, some benzopyran derivatives exhibit anti-HIV activities (Kashiwada et al., 2001). Similarly, isoxazolidine derivatives exhibit anti-fungal (Mullen et al., 1988), anti-inflammatory (Green et al., 1982) and other such biological activities. In this paper we report the synthesis and crystal structure of the title compound which comprises an isoxazole ring, trans-fused with the pyran ring of the chromene moiety, a methyl benzene ring and a carbonitrile group cis-attached to the adjacent carbon atoms and a benzene ring attached to the nitrogen atom of the isoxazole ring.

In the title molecule (Fig. 1), the six membered pyran ring adopts a half-chair conformation with puckering parameters (Cremer & Pople, 1975): Q = 0.487 (4) Å, θ = 54.1 (5)° and ϕ = 288.0 (5)°; the carbon atom C9 deviates from the mean plane by 0.654 (6) Å. The five membered isoxazole ring adopts an N-envelope conformation with N1 displaced by 0.742 (5) Å from the mean plane formed by the rest of the ring atoms. The carbonitrile side-chain is almost linear, with C–C–N angle of 178.6 (5)°, which is in agreement with the observations made in another similar reported structure (Swaminathan et al., 2011).

The molecular structure is stabilized by a C—H···Cg1 intramolecular interaction (Fig 1); Cg1 is the center of gravity of the phenyl ring (C19–C24). The crystal packing is stabilized by two C–H···N intermolecular interactions, through bifurcated hydrogen bonds formed between the carbonitrile N atom and two alternate C atoms in the unsubstituted benzene ring and a C—H···Cg2 intermolecular interaction (Table 1); Cg2 is the center of gravity of the phenyl ring (C12–C17). The packing arrangement of the title compound is shown in Fig. 2.

Related literature top

For uses of benzopyran and isoxazolidine derivatives, see: Green et al. (1982); Kashiwada et al. (2001); Mullen et al. (1988). For a related structure, see: Swaminathan et al. (2011). For puckering parameters, see: Cremer & Pople (1975). For synthetic details, see: Bakthadoss & Murugan (2010).

Experimental top

The title compound was synthesized using Baylis–Hillman derivatives through in situ formation of nitrones followed by an intramolecular [3 + 2] dipolar cycloaddition reaction sequence (Bakthadoss & Murugan, 2010). A mixture of (E)-2-((2-Formylphenoxy)methyl)-3-o-tolylacrylonitrile (2 mmol, 0.75 g) and N-phenylhydroxylamine (3 mmol, 0.33 g) in ethanol (10 ml) was refluxed for 6 h. After the completion of the reaction, as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (15 ml) and extracted with ethyl acetate (3 x 15 ml). The combined organic layer was washed with brine (3 x 15 ml) and dried over anhydrous Na₂SO₄. The solvent was removed under reduced pressure. The crude mass was purified by column chromotography on silica gel (Acme 100–200 mesh), using ethyl acetate-hexane (1:9) to provide the pure title compound as a colourless solid in 80% yield. Block-shaped single crystals of the title compound suitable for X-ray diffraction analysis were obtained from a solution of ethyl acetate by slow evaporation at room temperature.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme, depicting the C—H···Cg intramolecular interaction as dashed line. Displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius.
	Fig. 2. Part of the crystal structure of the title compound viewed down the a axis; C—H···N and C—H···Cg intermolecular interactions are indicated by dashed lines.

(2S,5S,6R)-5-(4-Methylphenyl)-3-phenyl-4,8-dioxa-3- azatricyclo[7.4.0.0^2,6]trideca-1(13),9,11-triene-6-carbonitrile top

Crystal data top

C₂₄H₂₀N₂O₂	F(000) = 776
M_r = 368.42	D_x = 1.252 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4476 reflections
a = 8.9890 (16) Å	θ = 1.8–27.7°
b = 9.8432 (19) Å	µ = 0.08 mm⁻¹
c = 22.084 (4) Å	T = 293 K
V = 1954.0 (6) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4476 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 27.7°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→11
T_min = 0.976, T_max = 0.980	k = −9→12
10510 measured reflections	l = −28→28

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.252	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1392P)² + 0.1028P] where P = (F_o² + 2F_c²)/3
4476 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₂₀N₂O₂	V = 1954.0 (6) Å³
M_r = 368.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.9890 (16) Å	µ = 0.08 mm⁻¹
b = 9.8432 (19) Å	T = 293 K
c = 22.084 (4) Å	0.30 × 0.25 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4476 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2396 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.065
10510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.252	H-atom parameters constrained
S = 1.00	Δρ_max = 0.29 e Å⁻³
4476 reflections	Δρ_min = −0.33 e Å⁻³
254 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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

	x	y	z	U_iso*/U_eq
C1	0.7119 (5)	0.2084 (4)	0.21685 (18)	0.0428 (9)
C2	0.7325 (5)	0.0754 (4)	0.2349 (2)	0.0576 (12)
H2	0.6914	0.0050	0.2123	0.069*
C3	0.8128 (6)	0.0469 (5)	0.2855 (2)	0.0655 (14)
H3	0.8273	−0.0425	0.2977	0.079*
C4	0.8728 (6)	0.1533 (5)	0.3188 (2)	0.0605 (12)
H4	0.9273	0.1352	0.3537	0.073*
C5	0.8522 (5)	0.2841 (5)	0.30056 (17)	0.0522 (11)
H5	0.8937	0.3541	0.3232	0.063*
C6	0.7705 (4)	0.3161 (4)	0.24889 (16)	0.0414 (9)
C7	0.7539 (4)	0.4578 (4)	0.22771 (15)	0.0383 (9)
H7	0.8516	0.5017	0.2259	0.046*
C8	0.6754 (4)	0.4707 (4)	0.16629 (15)	0.0402 (9)
C9	0.5624 (5)	0.3556 (4)	0.1614 (2)	0.0533 (11)
H9A	0.4902	0.3641	0.1938	0.064*
H9B	0.5097	0.3632	0.1232	0.064*
C10	0.7823 (6)	0.4613 (5)	0.11672 (17)	0.0520 (11)
C11	0.5993 (5)	0.6120 (4)	0.17064 (17)	0.0459 (10)
H11	0.4913	0.5988	0.1703	0.055*
C12	0.6383 (5)	0.7144 (4)	0.12342 (16)	0.0448 (9)
C13	0.7633 (6)	0.7942 (5)	0.12838 (19)	0.0609 (13)
H13	0.8258	0.7839	0.1616	0.073*
C14	0.7971 (7)	0.8890 (5)	0.0848 (2)	0.0728 (15)
H14	0.8806	0.9436	0.0897	0.087*
C15	0.7101 (7)	0.9044 (5)	0.0344 (2)	0.0684 (15)
C16	0.5876 (7)	0.8215 (7)	0.0288 (2)	0.0774 (17)
H16	0.5266	0.8291	−0.0051	0.093*
C17	0.5550 (6)	0.7284 (6)	0.0726 (2)	0.0710 (15)
H17	0.4727	0.6724	0.0674	0.085*
C18	0.7427 (10)	1.0141 (8)	−0.0113 (3)	0.112 (3)
H18A	0.7231	0.9804	−0.0513	0.168*
H18B	0.8453	1.0404	−0.0083	0.168*
H18C	0.6805	1.0914	−0.0035	0.168*
C19	0.7143 (5)	0.5804 (4)	0.32222 (16)	0.0457 (10)
C20	0.6470 (6)	0.5344 (6)	0.37311 (17)	0.0678 (14)
H20	0.5608	0.4825	0.3703	0.081*
C21	0.7058 (8)	0.5643 (8)	0.4288 (2)	0.088 (2)
H21	0.6590	0.5329	0.4637	0.105*
C22	0.8317 (9)	0.6392 (7)	0.4334 (2)	0.091 (2)
H22	0.8712	0.6592	0.4713	0.110*
C23	0.9005 (8)	0.6853 (6)	0.3823 (2)	0.0874 (19)
H23	0.9874	0.7361	0.3853	0.105*
C24	0.8416 (6)	0.6567 (5)	0.3261 (2)	0.0658 (14)
H24	0.8877	0.6888	0.2912	0.079*
N1	0.6521 (4)	0.5396 (3)	0.26516 (13)	0.0454 (8)
N2	0.8669 (6)	0.4523 (5)	0.07901 (16)	0.0717 (13)
O1	0.6300 (4)	0.2284 (3)	0.16486 (13)	0.0585 (8)
O2	0.6411 (4)	0.6622 (3)	0.22807 (11)	0.0539 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.037 (2)	0.033 (2)	0.059 (2)	0.0030 (18)	0.0031 (18)	0.0012 (18)
C2	0.045 (3)	0.030 (2)	0.098 (3)	0.002 (2)	0.007 (3)	0.000 (2)
C3	0.051 (3)	0.041 (3)	0.105 (4)	0.006 (2)	0.014 (3)	0.023 (3)
C4	0.053 (3)	0.054 (3)	0.074 (3)	0.019 (3)	0.000 (2)	0.015 (2)
C5	0.053 (3)	0.046 (2)	0.057 (2)	0.007 (2)	−0.003 (2)	0.003 (2)
C6	0.034 (2)	0.039 (2)	0.0515 (19)	0.0039 (18)	0.0058 (16)	0.0040 (17)
C7	0.036 (2)	0.035 (2)	0.0440 (18)	0.0044 (17)	0.0030 (16)	−0.0010 (17)
C8	0.034 (2)	0.039 (2)	0.0475 (19)	0.0019 (18)	0.0014 (16)	0.0024 (17)
C9	0.048 (3)	0.045 (3)	0.067 (3)	−0.005 (2)	−0.008 (2)	−0.002 (2)
C10	0.066 (3)	0.048 (2)	0.0419 (19)	0.007 (2)	0.002 (2)	0.0000 (19)
C11	0.038 (2)	0.049 (2)	0.051 (2)	0.0084 (19)	−0.0003 (17)	0.0013 (19)
C12	0.041 (3)	0.044 (2)	0.0493 (19)	0.006 (2)	0.0000 (18)	0.0058 (18)
C13	0.060 (3)	0.057 (3)	0.065 (3)	0.002 (3)	−0.011 (2)	0.015 (2)
C14	0.067 (4)	0.057 (3)	0.095 (4)	−0.006 (3)	0.003 (3)	0.019 (3)
C15	0.082 (4)	0.059 (3)	0.064 (3)	0.023 (3)	0.010 (3)	0.020 (3)
C16	0.077 (4)	0.096 (5)	0.059 (3)	0.011 (4)	−0.011 (3)	0.024 (3)
C17	0.066 (4)	0.077 (4)	0.070 (3)	−0.008 (3)	−0.022 (2)	0.012 (3)
C18	0.126 (7)	0.102 (5)	0.108 (4)	0.023 (5)	0.016 (4)	0.055 (4)
C19	0.053 (3)	0.039 (2)	0.046 (2)	0.009 (2)	0.0059 (18)	0.0024 (18)
C20	0.062 (3)	0.091 (4)	0.050 (2)	0.001 (3)	0.009 (2)	0.007 (3)
C21	0.100 (5)	0.116 (6)	0.048 (3)	0.003 (5)	0.009 (3)	0.000 (3)
C22	0.135 (7)	0.083 (4)	0.056 (3)	−0.002 (5)	−0.016 (3)	−0.018 (3)
C23	0.117 (5)	0.068 (4)	0.077 (3)	−0.033 (4)	−0.016 (3)	−0.011 (3)
C24	0.085 (4)	0.052 (3)	0.061 (2)	−0.018 (3)	−0.001 (3)	−0.004 (2)
N1	0.046 (2)	0.0425 (19)	0.0473 (16)	0.0103 (18)	0.0050 (15)	0.0043 (15)
N2	0.076 (3)	0.083 (3)	0.056 (2)	0.017 (3)	0.009 (2)	0.003 (2)
O1	0.065 (2)	0.0405 (17)	0.0696 (18)	−0.0055 (16)	−0.0100 (16)	−0.0047 (14)
O2	0.067 (2)	0.0478 (17)	0.0469 (13)	0.0153 (17)	0.0043 (14)	0.0060 (13)

Geometric parameters (Å, º) top

C1—C6	1.379 (5)	C12—C13	1.376 (6)
C1—O1	1.378 (5)	C13—C14	1.373 (6)
C1—C2	1.381 (5)	C13—H13	0.9300
C2—C3	1.360 (7)	C14—C15	1.369 (7)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.388 (7)	C15—C16	1.376 (8)
C3—H3	0.9300	C15—C18	1.507 (7)
C4—C5	1.362 (6)	C16—C17	1.364 (7)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.393 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.478 (5)	C18—H18B	0.9600
C7—N1	1.473 (5)	C18—H18C	0.9600
C7—C8	1.534 (5)	C19—C20	1.354 (6)
C7—H7	0.9800	C19—C24	1.371 (7)
C8—C10	1.459 (6)	C19—N1	1.436 (5)
C8—C9	1.526 (6)	C20—C21	1.371 (7)
C8—C11	1.553 (6)	C20—H20	0.9300
C9—O1	1.394 (5)	C21—C22	1.355 (10)
C9—H9A	0.9700	C21—H21	0.9300
C9—H9B	0.9700	C22—C23	1.365 (8)
C10—N2	1.131 (6)	C22—H22	0.9300
C11—O2	1.412 (5)	C23—C24	1.377 (7)
C11—C12	1.492 (5)	C23—H23	0.9300
C11—H11	0.9800	C24—H24	0.9300
C12—C17	1.357 (6)	N1—O2	1.461 (4)

C6—C1—O1	121.4 (3)	C13—C12—C11	121.5 (4)
C6—C1—C2	122.0 (4)	C12—C13—C14	120.8 (4)
O1—C1—C2	116.6 (4)	C12—C13—H13	119.6
C3—C2—C1	120.3 (4)	C14—C13—H13	119.6
C3—C2—H2	119.9	C15—C14—C13	121.2 (5)
C1—C2—H2	119.9	C15—C14—H14	119.4
C2—C3—C4	119.1 (4)	C13—C14—H14	119.4
C2—C3—H3	120.5	C14—C15—C16	117.7 (5)
C4—C3—H3	120.5	C14—C15—C18	120.9 (6)
C5—C4—C3	120.2 (4)	C16—C15—C18	121.3 (6)
C5—C4—H4	119.9	C17—C16—C15	120.4 (5)
C3—C4—H4	119.9	C17—C16—H16	119.8
C4—C5—C6	121.9 (4)	C15—C16—H16	119.8
C4—C5—H5	119.1	C12—C17—C16	122.5 (5)
C6—C5—H5	119.1	C12—C17—H17	118.8
C1—C6—C5	116.6 (4)	C16—C17—H17	118.8
C1—C6—C7	121.6 (3)	C15—C18—H18A	109.5
C5—C6—C7	121.7 (4)	C15—C18—H18B	109.5
N1—C7—C6	113.6 (3)	H18A—C18—H18B	109.5
N1—C7—C8	99.5 (3)	C15—C18—H18C	109.5
C6—C7—C8	113.8 (3)	H18A—C18—H18C	109.5
N1—C7—H7	109.8	H18B—C18—H18C	109.5
C6—C7—H7	109.8	C20—C19—C24	120.2 (4)
C8—C7—H7	109.8	C20—C19—N1	117.5 (4)
C10—C8—C9	109.8 (4)	C24—C19—N1	122.2 (4)
C10—C8—C7	110.8 (3)	C19—C20—C21	120.1 (6)
C9—C8—C7	107.9 (3)	C19—C20—H20	120.0
C10—C8—C11	113.1 (3)	C21—C20—H20	120.0
C9—C8—C11	112.1 (3)	C22—C21—C20	120.4 (5)
C7—C8—C11	102.8 (3)	C22—C21—H21	119.8
O1—C9—C8	111.9 (4)	C20—C21—H21	119.8
O1—C9—H9A	109.2	C23—C22—C21	119.8 (5)
C8—C9—H9A	109.2	C23—C22—H22	120.1
O1—C9—H9B	109.2	C21—C22—H22	120.1
C8—C9—H9B	109.2	C22—C23—C24	120.2 (6)
H9A—C9—H9B	107.9	C22—C23—H23	119.9
N2—C10—C8	178.6 (5)	C24—C23—H23	119.9
O2—C11—C12	109.2 (3)	C19—C24—C23	119.3 (5)
O2—C11—C8	104.6 (3)	C19—C24—H24	120.3
C12—C11—C8	117.3 (3)	C23—C24—H24	120.3
O2—C11—H11	108.5	C19—N1—O2	106.7 (3)
C12—C11—H11	108.5	C19—N1—C7	113.8 (3)
C8—C11—H11	108.5	O2—N1—C7	100.3 (3)
C17—C12—C13	117.3 (4)	C1—O1—C9	114.0 (3)
C17—C12—C11	121.2 (4)	C11—O2—N1	103.5 (3)

C6—C1—C2—C3	−0.1 (7)	C17—C12—C13—C14	3.3 (7)
O1—C1—C2—C3	179.6 (4)	C11—C12—C13—C14	−179.4 (5)
C1—C2—C3—C4	0.3 (7)	C12—C13—C14—C15	−1.8 (8)
C2—C3—C4—C5	−0.5 (8)	C13—C14—C15—C16	−0.1 (8)
C3—C4—C5—C6	0.4 (8)	C13—C14—C15—C18	176.3 (5)
O1—C1—C6—C5	−179.6 (3)	C14—C15—C16—C17	0.5 (9)
C2—C1—C6—C5	0.1 (6)	C18—C15—C16—C17	−176.0 (6)
O1—C1—C6—C7	−2.6 (6)	C13—C12—C17—C16	−3.0 (8)
C2—C1—C6—C7	177.1 (4)	C11—C12—C17—C16	179.7 (5)
C4—C5—C6—C1	−0.2 (6)	C15—C16—C17—C12	1.2 (9)
C4—C5—C6—C7	−177.2 (4)	C24—C19—C20—C21	0.2 (8)
C1—C6—C7—N1	109.5 (4)	N1—C19—C20—C21	176.7 (5)
C5—C6—C7—N1	−73.6 (5)	C19—C20—C21—C22	−0.3 (10)
C1—C6—C7—C8	−3.5 (5)	C20—C21—C22—C23	0.0 (11)
C5—C6—C7—C8	173.4 (3)	C21—C22—C23—C24	0.5 (10)
N1—C7—C8—C10	150.9 (3)	C20—C19—C24—C23	0.3 (8)
C6—C7—C8—C10	−87.8 (4)	N1—C19—C24—C23	−176.0 (5)
N1—C7—C8—C9	−88.8 (4)	C22—C23—C24—C19	−0.7 (9)
C6—C7—C8—C9	32.4 (4)	C20—C19—N1—O2	132.9 (4)
N1—C7—C8—C11	29.8 (4)	C24—C19—N1—O2	−50.7 (5)
C6—C7—C8—C11	151.0 (3)	C20—C19—N1—C7	−117.4 (4)
C10—C8—C9—O1	60.6 (4)	C24—C19—N1—C7	59.0 (5)
C7—C8—C9—O1	−60.3 (4)	C6—C7—N1—C19	75.1 (4)
C11—C8—C9—O1	−172.8 (3)	C8—C7—N1—C19	−163.5 (3)
C10—C8—C11—O2	−118.3 (4)	C6—C7—N1—O2	−171.3 (3)
C9—C8—C11—O2	116.9 (4)	C8—C7—N1—O2	−49.9 (3)
C7—C8—C11—O2	1.3 (4)	C6—C1—O1—C9	−24.7 (5)
C10—C8—C11—C12	2.8 (5)	C2—C1—O1—C9	155.6 (4)
C9—C8—C11—C12	−122.0 (4)	C8—C9—O1—C1	57.2 (5)
C7—C8—C11—C12	122.4 (4)	C12—C11—O2—N1	−158.9 (3)
O2—C11—C12—C17	−147.9 (4)	C8—C11—O2—N1	−32.6 (4)
C8—C11—C12—C17	93.4 (5)	C19—N1—O2—C11	172.2 (3)
O2—C11—C12—C13	34.9 (5)	C7—N1—O2—C11	53.3 (4)
C8—C11—C12—C13	−83.8 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C19–C24 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1	0.93	2.99	3.701 (5)	134
C20—H20···Cg2ⁱ	0.93	2.95	3.803 (6)	153
C21—H21···N2ⁱⁱ	0.93	2.56	3.385 (6)	148
C23—H23···N2ⁱⁱⁱ	0.93	2.62	3.466 (7)	151

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₂
M_r	368.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.9890 (16), 9.8432 (19), 22.084 (4)
V (Å³)	1954.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.976, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	10510, 4476, 2396
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.252, 1.00
No. of reflections	4476
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.33

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C19–C24 and C12–C17 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1	0.93	2.99	3.701 (5)	134
C20—H20···Cg2ⁱ	0.93	2.95	3.803 (6)	153
C21—H21···N2ⁱⁱ	0.93	2.56	3.385 (6)	148
C23—H23···N2ⁱⁱⁱ	0.93	2.62	3.466 (7)	151

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection. K. Swaminathan and K. Sethusankar thank Dr V. Murugan, Head of the Department of Physics, RKM Vivekananda College, Chennai, India, for providing facilities in the department to carry out this work.

References

Bakthadoss, M. & Murugan, G. (2010). Eur. J. Org. Chem. pp. 5825–5830. Web of Science CSD CrossRef Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Green, M. J., Tiberi, R. L., Friary, R., Lutsky, B. N., Berkenkoph, J., Fernandez, X. & Monahan, M. (1982). J. Med. Chem. 25, 1492–1495. CrossRef CAS PubMed Web of Science Google Scholar
Kashiwada, Y., Yamazaki, K., Ikeshiro, Y., Yamagishi, T., Fujioka, T., Mihashi, K., Mizuki, K., Cosentino, L. M., Fowke, K., Natschke, S. L. M. & Lee, K. H. (2001). Tetrahedron, 57, 1559–1563. Web of Science CSD CrossRef CAS Google Scholar
Mullen, G. B., DeCory, T. R., Mitchell, J. T., Allen, S. D., Kinsolving, C. R. & Georgiev, V. S. (1988). J. Med. Chem. 31, 2008–2014. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 2| February 2012| Pages o283-o284

doi:10.1107/S1600536811055413

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

(2S,5S,6R)-5-(4-Methyl­phen­yl)-3-phenyl-4,8-dioxa-3-aza­tri­cyclo­[7.4.0.02,6]trideca-1(13),9,11-triene-6-carbo­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2S,5S,6R)-5-(4-Methylphenyl)-3-phenyl-4,8-dioxa-3-azatricyclo[7.4.0.0^2,6]trideca-1(13),9,11-triene-6-carbonitrile