Literature DB >> 23424466

3-(2-Methyl-phen-yl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo-nitrile.

G Suresh¹, J Srinivasan, M Bakthadoss, S Aravindhan.

Abstract

In the title compound, C(18)H(14)N(2)O(2), the pyran ring of the chromeno ring system has a half-chair conformation, and the dihedral angle between its mean plane and the benzene ring is 5.3 (2)°. The isoxazole ring forms a dihedral angle of 74.6 (2)° with the attached benzene ring and is inclined to the mean plane of the chromeno ring system by 15.06 (19)°. In the crystal, there are no significant inter-molecular inter-actions.

Entities: Chemical Disease Species

Year: 2013 PMID： 23424466 PMCID： PMC3569243 DOI： 10.1107/S1600536812051732

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007 ▶, 2008 ▶); Cai et al. (2006 ▶); Gabor (1988 ▶); Brooks (1998 ▶); Valenti et al. (1993 ▶); Hyana & Saimoto (1987 ▶); Tang et al. (2007 ▶). For related structures, see: Gangadharan et al. (2011 ▶); Swaminathan et al. (2011 ▶).

Experimental

Crystal data

C18H14N2O2 M = 290.31 Orthorhombic, a = 19.326 (3) Å b = 10.7866 (17) Å c = 6.9072 (11) Å V = 1439.9 (4) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 298 K 0.35 × 0.25 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.970, T max = 0.987 4742 measured reflections 1750 independent reflections 1100 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.059 wR(F 2) = 0.146 S = 1.09 1750 reflections 200 parameters 1 restraint H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.17 e Å−3 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, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051732/su2544sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051732/su2544Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812051732/su2544Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₄N₂O₂	F(000) = 608
M_r = 290.31	D_x = 1.339 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1750 reflections
a = 19.326 (3) Å	θ = 1.9–27.7°
b = 10.7866 (17) Å	µ = 0.09 mm⁻¹
c = 6.9072 (11) Å	T = 298 K
V = 1439.9 (4) Å³	Orthorhombic, colourless
Z = 4	0.35 × 0.25 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	1750 independent reflections
Radiation source: fine-focus sealed tube	1100 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω and φ scans	θ_max = 27.7°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −24→25
T_min = 0.970, T_max = 0.987	k = −10→13
4742 measured reflections	l = −8→6

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0456P)² + 0.5663P] where P = (F_o² + 2F_c²)/3
1750 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
C1	0.8559 (2)	−0.2941 (4)	0.6812 (9)	0.0493 (12)
C2	0.8529 (2)	−0.4218 (5)	0.6834 (12)	0.0659 (16)
H2	0.8639	−0.4667	0.5727	0.079*
C3	0.8336 (3)	−0.4824 (5)	0.8491 (13)	0.0725 (18)
H3	0.8311	−0.5685	0.8502	0.087*
C4	0.8177 (2)	−0.4155 (6)	1.0168 (11)	0.0717 (18)
H4	0.8053	−0.4572	1.1294	0.086*
C5	0.8204 (2)	−0.2907 (5)	1.0155 (9)	0.0597 (14)
H5	0.8093	−0.2470	1.1274	0.072*
C6	0.8397 (2)	−0.2254 (5)	0.8478 (8)	0.0494 (13)
C7	0.84595 (19)	−0.0931 (5)	0.8391 (7)	0.0421 (12)
C8	0.8522 (2)	0.0964 (4)	0.6809 (8)	0.0457 (11)
H8	0.8093	0.1013	0.6058	0.055*
C9	0.88122 (19)	−0.0358 (4)	0.6634 (7)	0.0384 (10)
C10	0.8602 (2)	−0.1104 (5)	0.4876 (8)	0.0482 (12)
H10A	0.8109	−0.1007	0.4659	0.058*
H10B	0.8842	−0.0789	0.3746	0.058*
C11	0.8981 (2)	0.2017 (4)	0.6220 (7)	0.0434 (12)
C12	0.9523 (2)	0.2369 (4)	0.7453 (9)	0.0558 (14)
H12	0.9572	0.1988	0.8653	0.067*
C13	0.9984 (2)	0.3274 (5)	0.6900 (11)	0.0674 (17)
H13	1.0337	0.3520	0.7733	0.081*
C14	0.9919 (3)	0.3817 (5)	0.5095 (13)	0.0744 (19)
H14	1.0239	0.4406	0.4686	0.089*
C15	0.9383 (3)	0.3483 (5)	0.3917 (9)	0.0618 (14)
H15	0.9341	0.3865	0.2716	0.074*
C16	0.8901 (2)	0.2600 (4)	0.4442 (8)	0.0474 (12)
C17	0.8323 (3)	0.2283 (5)	0.3092 (9)	0.0668 (15)
H17A	0.7888	0.2425	0.3726	0.100*
H17B	0.8357	0.1426	0.2726	0.100*
H17C	0.8353	0.2793	0.1957	0.100*
C18	0.9575 (2)	−0.0430 (4)	0.6899 (7)	0.0412 (10)
N1	0.82063 (19)	−0.0141 (4)	0.9557 (7)	0.0556 (11)
N2	1.01564 (18)	−0.0484 (4)	0.7066 (7)	0.0570 (11)
O1	0.87563 (16)	−0.2367 (3)	0.5112 (6)	0.0556 (9)
O2	0.83494 (17)	0.1062 (3)	0.8863 (5)	0.0582 (9)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (2)	0.057 (3)	0.054 (3)	−0.001 (2)	0.006 (2)	−0.002 (3)
C2	0.054 (3)	0.056 (4)	0.088 (5)	0.003 (2)	0.001 (3)	−0.021 (4)
C3	0.059 (3)	0.048 (3)	0.110 (6)	−0.003 (2)	−0.006 (3)	0.005 (4)
C4	0.051 (3)	0.083 (4)	0.081 (5)	0.001 (3)	0.006 (3)	0.025 (5)
C5	0.050 (3)	0.075 (4)	0.055 (4)	0.008 (3)	0.008 (3)	0.005 (3)
C6	0.034 (2)	0.069 (3)	0.046 (3)	0.002 (2)	0.003 (2)	−0.002 (3)
C7	0.035 (2)	0.058 (3)	0.033 (3)	0.004 (2)	0.0013 (19)	−0.009 (3)
C8	0.043 (2)	0.056 (3)	0.038 (3)	0.003 (2)	−0.004 (2)	−0.005 (3)
C9	0.042 (2)	0.045 (2)	0.029 (2)	0.0030 (18)	0.0034 (19)	−0.007 (2)
C10	0.047 (2)	0.062 (3)	0.036 (3)	0.001 (2)	0.004 (2)	−0.009 (3)
C11	0.041 (2)	0.042 (3)	0.047 (3)	0.0072 (19)	0.001 (2)	−0.015 (2)
C12	0.054 (3)	0.055 (3)	0.057 (4)	0.010 (2)	−0.014 (2)	−0.004 (3)
C13	0.050 (3)	0.056 (3)	0.097 (5)	−0.001 (2)	−0.019 (3)	−0.012 (4)
C14	0.055 (3)	0.062 (4)	0.106 (6)	−0.001 (2)	0.003 (3)	−0.001 (4)
C15	0.065 (3)	0.064 (3)	0.057 (4)	0.008 (3)	0.005 (3)	−0.003 (3)
C16	0.051 (2)	0.044 (3)	0.047 (3)	0.009 (2)	0.001 (2)	−0.010 (3)
C17	0.087 (4)	0.068 (4)	0.045 (4)	−0.005 (3)	−0.015 (3)	0.005 (3)
C18	0.044 (2)	0.049 (3)	0.030 (2)	0.0022 (19)	0.007 (2)	−0.004 (2)
N1	0.052 (2)	0.071 (3)	0.043 (3)	0.003 (2)	0.0102 (18)	−0.008 (2)
N2	0.041 (2)	0.072 (3)	0.057 (3)	0.0055 (18)	0.001 (2)	−0.007 (3)
O1	0.068 (2)	0.053 (2)	0.045 (2)	0.0031 (17)	0.0091 (18)	−0.0161 (19)
O2	0.070 (2)	0.062 (2)	0.042 (2)	0.0082 (16)	0.0097 (17)	−0.012 (2)

C1—C2	1.379 (7)	C10—O1	1.405 (6)
C1—O1	1.381 (7)	C10—H10A	0.9700
C1—C6	1.404 (7)	C10—H10B	0.9700
C2—C3	1.370 (10)	C11—C16	1.388 (7)
C2—H2	0.9300	C11—C12	1.403 (6)
C3—C4	1.399 (9)	C12—C13	1.376 (7)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.347 (8)	C13—C14	1.383 (10)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.406 (7)	C14—C15	1.365 (8)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.433 (7)	C15—C16	1.381 (7)
C7—N1	1.271 (6)	C15—H15	0.9300
C7—C9	1.523 (6)	C16—C17	1.495 (7)
C8—O2	1.461 (6)	C17—H17A	0.9600
C8—C11	1.497 (6)	C17—H17B	0.9600
C8—C9	1.537 (6)	C17—H17C	0.9600
C8—H8	0.9800	C18—N2	1.131 (5)
C9—C18	1.487 (5)	N1—O2	1.410 (5)
C9—C10	1.512 (7)

C2—C1—O1	118.0 (5)	O1—C10—H10A	109.3
C2—C1—C6	120.6 (6)	C9—C10—H10A	109.3
O1—C1—C6	121.5 (4)	O1—C10—H10B	109.3
C3—C2—C1	119.8 (6)	C9—C10—H10B	109.3
C3—C2—H2	120.1	H10A—C10—H10B	108.0
C1—C2—H2	120.1	C16—C11—C12	119.8 (4)
C2—C3—C4	120.4 (5)	C16—C11—C8	121.2 (4)
C2—C3—H3	119.8	C12—C11—C8	118.9 (5)
C4—C3—H3	119.8	C13—C12—C11	120.5 (6)
C5—C4—C3	120.1 (6)	C13—C12—H12	119.8
C5—C4—H4	119.9	C11—C12—H12	119.8
C3—C4—H4	119.9	C12—C13—C14	119.5 (5)
C4—C5—C6	121.0 (6)	C12—C13—H13	120.3
C4—C5—H5	119.5	C14—C13—H13	120.3
C6—C5—H5	119.5	C15—C14—C13	119.6 (6)
C1—C6—C5	118.0 (5)	C15—C14—H14	120.2
C1—C6—C7	118.2 (5)	C13—C14—H14	120.2
C5—C6—C7	123.7 (5)	C14—C15—C16	122.5 (6)
N1—C7—C6	127.5 (4)	C14—C15—H15	118.7
N1—C7—C9	113.8 (4)	C16—C15—H15	118.7
C6—C7—C9	118.4 (4)	C15—C16—C11	118.0 (5)
O2—C8—C11	110.1 (4)	C15—C16—C17	119.9 (5)
O2—C8—C9	103.1 (4)	C11—C16—C17	122.1 (4)
C11—C8—C9	117.8 (4)	C16—C17—H17A	109.5
O2—C8—H8	108.5	C16—C17—H17B	109.5
C11—C8—H8	108.5	H17A—C17—H17B	109.5
C9—C8—H8	108.5	C16—C17—H17C	109.5
C18—C9—C10	109.7 (3)	H17A—C17—H17C	109.5
C18—C9—C7	108.9 (4)	H17B—C17—H17C	109.5
C10—C9—C7	107.6 (3)	N2—C18—C9	178.8 (5)
C18—C9—C8	113.6 (3)	C7—N1—O2	109.1 (4)
C10—C9—C8	117.3 (4)	C1—O1—C10	118.3 (4)
C7—C9—C8	98.7 (4)	N1—O2—C8	107.9 (3)
O1—C10—C9	111.5 (4)

O1—C1—C2—C3	179.9 (4)	C18—C9—C10—O1	62.9 (5)
C6—C1—C2—C3	0.4 (7)	C7—C9—C10—O1	−55.5 (4)
C1—C2—C3—C4	−0.8 (8)	C8—C9—C10—O1	−165.5 (4)
C2—C3—C4—C5	0.9 (8)	O2—C8—C11—C16	−140.8 (4)
C3—C4—C5—C6	−0.7 (7)	C9—C8—C11—C16	101.4 (5)
C2—C1—C6—C5	−0.2 (6)	O2—C8—C11—C12	42.6 (5)
O1—C1—C6—C5	−179.7 (4)	C9—C8—C11—C12	−75.2 (6)
C2—C1—C6—C7	177.9 (4)	C16—C11—C12—C13	−1.1 (7)
O1—C1—C6—C7	−1.5 (6)	C8—C11—C12—C13	175.5 (5)
C4—C5—C6—C1	0.3 (7)	C11—C12—C13—C14	−1.5 (8)
C4—C5—C6—C7	−177.7 (4)	C12—C13—C14—C15	2.6 (8)
C1—C6—C7—N1	163.8 (4)	C13—C14—C15—C16	−1.0 (9)
C5—C6—C7—N1	−18.2 (7)	C14—C15—C16—C11	−1.5 (7)
C1—C6—C7—C9	−10.4 (5)	C14—C15—C16—C17	179.5 (5)
C5—C6—C7—C9	167.6 (4)	C12—C11—C16—C15	2.6 (6)
N1—C7—C9—C18	103.9 (4)	C8—C11—C16—C15	−174.0 (4)
C6—C7—C9—C18	−81.1 (4)	C12—C11—C16—C17	−178.5 (5)
N1—C7—C9—C10	−137.2 (4)	C8—C11—C16—C17	5.0 (6)
C6—C7—C9—C10	37.8 (5)	C6—C7—N1—O2	−175.9 (4)
N1—C7—C9—C8	−14.8 (5)	C9—C7—N1—O2	−1.4 (5)
C6—C7—C9—C8	160.2 (4)	C2—C1—O1—C10	162.0 (4)
O2—C8—C9—C18	−91.3 (4)	C6—C1—O1—C10	−18.6 (6)
C11—C8—C9—C18	30.2 (7)	C9—C10—O1—C1	48.4 (5)
O2—C8—C9—C10	138.9 (4)	C7—N1—O2—C8	18.6 (4)
C11—C8—C9—C10	−99.6 (5)	C11—C8—O2—N1	−153.6 (3)
O2—C8—C9—C7	23.9 (4)	C9—C8—O2—N1	−27.1 (4)
C11—C8—C9—C7	145.4 (4)

8 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

Review 2. A chemical genetics approach for the discovery of apoptosis inducers: from phenotypic cell based HTS assay and structure-activity relationship studies, to identification of potential anticancer agents and molecular targets.

Authors: Sui Xiong Cai; John Drewe; Shailaja Kasibhatla
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3. Benzo-gamma-pyrone analogues of geiparvarin: synthesis and biological evaluation against B16 melanoma cells.

Authors: P Valenti; P Da Re; A Rampa; P Montanari; M Carrara; L Cima
Journal: Anticancer Drug Des Date: 1993-10

4. Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based HTS assay. Part 5: modifications of the 2- and 3-positions.

Authors: William Kemnitzer; Songchun Jiang; Yan Wang; Shailaja Kasibhatla; Candace Crogan-Grundy; Monica Bubenik; Denis Labrecque; Real Denis; Serge Lamothe; Giorgio Attardo; Henriette Gourdeau; Ben Tseng; John Drewe; Sui Xiong Cai
Journal: Bioorg Med Chem Lett Date: 2007-11-28 Impact factor: 2.823