4'-Methyl-3-(4-nitro-phen-yl)-4-phenyl-4,5,1',2',3',4'-hexa-hydro-spiro-[isoxazole-5,2'-naphthalen]-1'-one.

The title compound, C(25)H(20)N(2)O(4), is a new spiro-isoxazoline derivative. It contains a five-membered isoxazoline ring (A), a tetra-lone unit (E and D), a 4-nitro-phenyl substituent (B), and a phenyl ring (C). The isoxazoline ring (A) has an envelope conformation, while the cyclo-hexenone ring (D) has an inter-mediate sofa/half-chair conformation. The aromatic ring of the 4-nitro-phenyl substituent (B) is inclined at an angle of 78.97 (10)° to the phenyl ring (C). The rigid pharmacophore site, Osp(2)-C-C-Osp(3), is characterized by an O⋯O distance of 3.113 (2) Å and an O-C-C-O torsion angle of 97.8 (2)°. In the crystal structure, mol-ecules are linked by C-H⋯O contacts.

Related literature

For the crystal structure of a very similar compound, 3-(4-chloro­phen­yl)-4-(4-phenyl-3′,4′-dihydro-1′H,4H-spiro­[isoxazole-5,2′-naphthalen]-1′-one, see: Subbiah Pandi et al. (2001 ▶). For related literature, see: Anaflous et al. (2004 ▶); Arnold et al. (1947 ▶); Bakavoli et al. (2005 ▶); Chaouni-Benabdallah et al. (2001 ▶); Chenera et al. (1993 ▶); Debaerdemaeker et al. (1977 ▶); Ellis (1997 ▶); Howe & Shelton (1990 ▶); Katritzky et al. (2003 ▶); Kerbal et al. (1990 ▶); Kooijman et al. (1984 ▶); Seifert et al. (1976 ▶); Smietana et al. (1999 ▶).

Experimental

Crystal data

C25H20N2O4

M = 412.43

Monoclinic,

a = 10.6567 (15) Å

b = 15.7071 (16) Å

c = 12.7259 (15) Å

β = 106.258 (10)°

V = 2045.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (2) K

0.40 × 0.37 × 0.27 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: none

20256 measured reflections

3798 independent reflections

2837 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.123

S = 1.01

3798 reflections

283 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807066470/bg2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066470/bg2153Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C25H20N2O4	F000 = 864
Mr = 412.43	Dx = 1.340 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11994 reflections
a = 10.6567 (15) Å	θ = 1.7–29.4º
b = 15.7071 (16) Å	µ = 0.09 mm−1
c = 12.7259 (15) Å	T = 173 (2) K
β = 106.258 (10)º	Plate, colourless
V = 2045.0 (4) Å3	0.40 × 0.37 × 0.27 mm
Z = 4

Stoe IPDSII diffractometer	2837 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.076
Monochromator: graphite	θmax = 25.5º
T = 173(2) K	θmin = 2.1º
φ and ω scans	h = −12→12
Absorption correction: none	k = −18→19
20256 measured reflections	l = −15→15
3798 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0704P)2 + 0.2039P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.52 e Å−3
3798 reflections	Δρmin = −0.21 e Å−3
283 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0074 (14)
Secondary atom site location: difference Fourier map

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Uiso*/Ueq
O1	0.47898 (16)	0.55329 (9)	0.36239 (13)	0.0422 (5)
O2	0.32596 (13)	0.43601 (8)	0.17246 (10)	0.0297 (4)
O3	−0.1326 (2)	0.35498 (16)	0.60945 (19)	0.0861 (9)
O4	−0.26968 (17)	0.41232 (14)	0.47131 (16)	0.0632 (7)
N1	0.21389 (15)	0.44017 (10)	0.20955 (13)	0.0281 (5)
N2	−0.1598 (2)	0.38712 (13)	0.51976 (18)	0.0490 (8)
C1	0.44094 (18)	0.42092 (11)	0.26695 (15)	0.0248 (5)
C2	0.5302 (2)	0.36112 (12)	0.22914 (17)	0.0338 (7)
C3	0.5692 (2)	0.39637 (14)	0.13022 (19)	0.0415 (8)
C4	0.62172 (19)	0.48610 (13)	0.15022 (16)	0.0333 (6)
C5	0.7052 (2)	0.51874 (16)	0.09383 (19)	0.0464 (8)
C6	0.7473 (2)	0.60217 (18)	0.1075 (2)	0.0556 (9)
C7	0.7069 (3)	0.65532 (17)	0.1772 (2)	0.0541 (9)
C8	0.6247 (2)	0.62468 (14)	0.23505 (18)	0.0414 (7)
C9	0.58332 (19)	0.54037 (12)	0.22298 (15)	0.0295 (6)
C10	0.50110 (18)	0.50975 (12)	0.29134 (15)	0.0273 (6)
C11	0.38311 (18)	0.39083 (11)	0.35863 (15)	0.0239 (5)
C12	0.24282 (18)	0.41746 (11)	0.30968 (15)	0.0243 (5)
C13	0.13979 (19)	0.41296 (11)	0.36551 (16)	0.0268 (6)
C14	0.1696 (2)	0.39216 (13)	0.47532 (17)	0.0348 (6)
C15	0.0720 (2)	0.38411 (14)	0.52679 (18)	0.0395 (7)
C16	−0.0553 (2)	0.39756 (13)	0.46671 (18)	0.0352 (7)
C17	−0.0876 (2)	0.42136 (15)	0.35887 (19)	0.0424 (7)
C18	0.0101 (2)	0.42881 (14)	0.30805 (17)	0.0379 (7)
C19	0.39453 (18)	0.29696 (11)	0.38701 (15)	0.0247 (5)
C20	0.48296 (19)	0.26972 (12)	0.48285 (16)	0.0299 (6)
C21	0.4922 (2)	0.18425 (14)	0.50951 (18)	0.0388 (7)
C22	0.4143 (2)	0.12540 (13)	0.4410 (2)	0.0396 (7)
C23	0.3264 (2)	0.15185 (13)	0.34565 (19)	0.0395 (7)
C24	0.3160 (2)	0.23724 (12)	0.31901 (17)	0.0337 (6)
C25	0.6582 (3)	0.33530 (18)	0.0947 (2)	0.0652 (11)
H2A	0.48560	0.30570	0.20930	0.0410*
H2B	0.61000	0.35120	0.29010	0.0410*
H3	0.48710	0.39970	0.06850	0.0500*
H5	0.73390	0.48300	0.04490	0.0560*
H6	0.80480	0.62300	0.06830	0.0670*
H7	0.73530	0.71290	0.18550	0.0650*
H8	0.59630	0.66130	0.28330	0.0500*
H11	0.42200	0.42500	0.42630	0.0290*
H14	0.25810	0.38330	0.51580	0.0420*
H15	0.09240	0.36960	0.60220	0.0470*
H17	−0.17600	0.43250	0.31980	0.0510*
H18	−0.01110	0.44490	0.23320	0.0450*
H20	0.53740	0.30980	0.53040	0.0360*
H21	0.55270	0.16590	0.57560	0.0470*
H22	0.42150	0.06670	0.45970	0.0480*
H23	0.27270	0.11140	0.29810	0.0470*
H24	0.25450	0.25530	0.25340	0.0400*
H25A	0.62010	0.27810	0.08750	0.0980*
H25B	0.74370	0.33450	0.14950	0.0980*
H25C	0.66880	0.35350	0.02410	0.0980*

	U11	U22	U33	U12	U13	U23
O1	0.0591 (10)	0.0291 (7)	0.0472 (9)	−0.0119 (7)	0.0295 (8)	−0.0113 (7)
O2	0.0284 (7)	0.0377 (7)	0.0232 (7)	−0.0041 (6)	0.0074 (6)	0.0007 (5)
O3	0.0793 (15)	0.1206 (19)	0.0782 (15)	0.0189 (13)	0.0549 (13)	0.0445 (14)
O4	0.0351 (10)	0.0973 (14)	0.0626 (12)	−0.0111 (9)	0.0225 (9)	−0.0100 (10)
N1	0.0258 (9)	0.0308 (8)	0.0279 (9)	−0.0031 (6)	0.0080 (7)	0.0005 (7)
N2	0.0529 (14)	0.0509 (12)	0.0537 (13)	−0.0081 (10)	0.0320 (11)	−0.0020 (10)
C1	0.0249 (9)	0.0252 (9)	0.0233 (9)	−0.0006 (7)	0.0052 (8)	−0.0002 (7)
C2	0.0381 (12)	0.0280 (10)	0.0394 (12)	0.0007 (8)	0.0174 (10)	−0.0039 (9)
C3	0.0483 (14)	0.0440 (12)	0.0388 (13)	−0.0024 (10)	0.0229 (11)	−0.0049 (9)
C4	0.0285 (10)	0.0418 (11)	0.0302 (10)	−0.0004 (8)	0.0090 (9)	0.0048 (9)
C5	0.0398 (13)	0.0619 (15)	0.0413 (13)	0.0004 (11)	0.0177 (10)	0.0084 (11)
C6	0.0426 (14)	0.0763 (18)	0.0515 (15)	−0.0168 (12)	0.0191 (12)	0.0148 (13)
C7	0.0576 (16)	0.0547 (15)	0.0491 (15)	−0.0289 (12)	0.0134 (12)	0.0060 (12)
C8	0.0447 (13)	0.0410 (12)	0.0370 (12)	−0.0137 (10)	0.0091 (10)	0.0020 (9)
C9	0.0263 (10)	0.0333 (10)	0.0268 (10)	−0.0055 (8)	0.0039 (8)	0.0031 (8)
C10	0.0267 (10)	0.0266 (9)	0.0275 (10)	−0.0007 (7)	0.0058 (8)	−0.0012 (8)
C11	0.0247 (9)	0.0228 (9)	0.0241 (9)	−0.0021 (7)	0.0068 (8)	−0.0025 (7)
C12	0.0256 (10)	0.0192 (8)	0.0266 (10)	−0.0008 (7)	0.0051 (8)	0.0004 (7)
C13	0.0296 (10)	0.0221 (9)	0.0299 (10)	0.0002 (7)	0.0105 (8)	0.0013 (7)
C14	0.0343 (11)	0.0371 (11)	0.0330 (11)	0.0079 (9)	0.0096 (9)	0.0048 (9)
C15	0.0500 (14)	0.0390 (11)	0.0342 (12)	0.0073 (10)	0.0194 (10)	0.0086 (9)
C16	0.0361 (12)	0.0322 (10)	0.0428 (12)	−0.0045 (8)	0.0200 (10)	−0.0014 (9)
C17	0.0291 (11)	0.0594 (14)	0.0391 (12)	−0.0026 (10)	0.0103 (9)	−0.0002 (10)
C18	0.0284 (11)	0.0540 (13)	0.0305 (11)	0.0005 (9)	0.0069 (9)	0.0026 (9)
C19	0.0255 (9)	0.0250 (9)	0.0261 (9)	0.0005 (7)	0.0113 (8)	0.0003 (7)
C20	0.0279 (10)	0.0327 (10)	0.0297 (11)	0.0045 (8)	0.0090 (8)	0.0020 (8)
C21	0.0384 (12)	0.0413 (12)	0.0401 (12)	0.0150 (10)	0.0166 (10)	0.0130 (10)
C22	0.0469 (13)	0.0241 (10)	0.0578 (14)	0.0072 (9)	0.0310 (12)	0.0089 (10)
C23	0.0456 (13)	0.0269 (10)	0.0501 (14)	−0.0027 (9)	0.0201 (11)	−0.0021 (9)
C24	0.0357 (11)	0.0298 (11)	0.0338 (11)	−0.0027 (8)	0.0070 (9)	−0.0010 (8)
C25	0.080 (2)	0.0611 (16)	0.0703 (19)	0.0055 (14)	0.0470 (17)	−0.0079 (14)

O1—C10	1.208 (2)	C17—C18	1.376 (3)
O2—N1	1.403 (2)	C19—C20	1.384 (3)
O2—C1	1.476 (2)	C19—C24	1.387 (3)
O3—N2	1.207 (3)	C20—C21	1.381 (3)
O4—N2	1.226 (3)	C21—C22	1.378 (3)
N1—C12	1.275 (2)	C22—C23	1.373 (3)
N2—C16	1.464 (3)	C23—C24	1.380 (3)
C1—C2	1.508 (3)	C2—H2A	0.9900
C1—C10	1.531 (3)	C2—H2B	0.9900
C1—C11	1.539 (3)	C3—H3	1.0000
C2—C3	1.535 (3)	C5—H5	0.9500
C3—C4	1.512 (3)	C6—H6	0.9500
C3—C25	1.505 (4)	C7—H7	0.9500
C4—C5	1.388 (3)	C8—H8	0.9500
C4—C9	1.401 (3)	C11—H11	1.0000
C5—C6	1.380 (4)	C14—H14	0.9500
C6—C7	1.372 (4)	C15—H15	0.9500
C7—C8	1.379 (4)	C17—H17	0.9500
C8—C9	1.391 (3)	C18—H18	0.9500
C9—C10	1.477 (3)	C20—H20	0.9500
C11—C12	1.509 (3)	C21—H21	0.9500
C11—C19	1.515 (2)	C22—H22	0.9500
C12—C13	1.467 (3)	C23—H23	0.9500
C13—C14	1.383 (3)	C24—H24	0.9500
C13—C18	1.393 (3)	C25—H25A	0.9800
C14—C15	1.381 (3)	C25—H25B	0.9800
C15—C16	1.374 (3)	C25—H25C	0.9800
C16—C17	1.370 (3)
N1—O2—C1	108.91 (13)	C20—C21—C22	120.5 (2)
O2—N1—C12	109.43 (15)	C21—C22—C23	119.8 (2)
O3—N2—O4	123.6 (2)	C22—C23—C24	119.9 (2)
O3—N2—C16	118.1 (2)	C19—C24—C23	120.73 (19)
O4—N2—C16	118.3 (2)	C1—C2—H2A	109.00
O2—C1—C2	107.10 (15)	C1—C2—H2B	109.00
O2—C1—C10	102.94 (14)	C3—C2—H2A	109.00
O2—C1—C11	104.46 (15)	C3—C2—H2B	109.00
C2—C1—C10	111.51 (16)	H2A—C2—H2B	108.00
C2—C1—C11	118.22 (15)	C2—C3—H3	107.00
C10—C1—C11	111.11 (15)	C4—C3—H3	107.00
C1—C2—C3	112.13 (16)	C25—C3—H3	106.00
C2—C3—C4	111.76 (18)	C4—C5—H5	119.00
C2—C3—C25	110.76 (19)	C6—C5—H5	119.00
C4—C3—C25	114.2 (2)	C5—C6—H6	120.00
C3—C4—C5	121.20 (19)	C7—C6—H6	120.00
C3—C4—C9	121.04 (18)	C6—C7—H7	120.00
C5—C4—C9	117.71 (19)	C8—C7—H7	120.00
C4—C5—C6	121.2 (2)	C7—C8—H8	120.00
C5—C6—C7	120.6 (2)	C9—C8—H8	120.00
C6—C7—C8	119.6 (2)	C1—C11—H11	109.00
C7—C8—C9	120.2 (2)	C12—C11—H11	109.00
C4—C9—C8	120.67 (19)	C19—C11—H11	109.00
C4—C9—C10	121.47 (17)	C13—C14—H14	120.00
C8—C9—C10	117.84 (18)	C15—C14—H14	120.00
O1—C10—C1	120.62 (18)	C14—C15—H15	121.00
O1—C10—C9	121.90 (18)	C16—C15—H15	121.00
C1—C10—C9	117.46 (16)	C16—C17—H17	121.00
C1—C11—C12	99.37 (15)	C18—C17—H17	121.00
C1—C11—C19	117.21 (15)	C13—C18—H18	120.00
C12—C11—C19	111.87 (16)	C17—C18—H18	120.00
N1—C12—C11	115.12 (17)	C19—C20—H20	120.00
N1—C12—C13	119.54 (18)	C21—C20—H20	120.00
C11—C12—C13	125.18 (16)	C20—C21—H21	120.00
C12—C13—C14	120.63 (19)	C22—C21—H21	120.00
C12—C13—C18	120.28 (18)	C21—C22—H22	120.00
C14—C13—C18	119.09 (19)	C23—C22—H22	120.00
C13—C14—C15	120.7 (2)	C22—C23—H23	120.00
C14—C15—C16	118.6 (2)	C24—C23—H23	120.00
N2—C16—C15	119.1 (2)	C19—C24—H24	120.00
N2—C16—C17	118.8 (2)	C23—C24—H24	120.00
C15—C16—C17	122.1 (2)	C3—C25—H25A	109.00
C16—C17—C18	118.9 (2)	C3—C25—H25B	109.00
C13—C18—C17	120.5 (2)	C3—C25—H25C	110.00
C11—C19—C20	120.03 (16)	H25A—C25—H25B	109.00
C11—C19—C24	121.02 (17)	H25A—C25—H25C	109.00
C20—C19—C24	118.94 (17)	H25B—C25—H25C	109.00
C19—C20—C21	120.07 (18)
C1—O2—N1—C12	−9.41 (18)	C5—C6—C7—C8	0.8 (4)
N1—O2—C1—C2	142.07 (14)	C6—C7—C8—C9	0.2 (4)
N1—O2—C1—C10	−100.27 (15)	C7—C8—C9—C4	−1.6 (3)
N1—O2—C1—C11	15.89 (17)	C7—C8—C9—C10	176.8 (2)
O2—N1—C12—C11	−1.6 (2)	C4—C9—C10—O1	172.0 (2)
O2—N1—C12—C13	−177.30 (15)	C4—C9—C10—C1	−9.7 (3)
O3—N2—C16—C15	−10.8 (3)	C8—C9—C10—O1	−6.3 (3)
O3—N2—C16—C17	169.9 (2)	C8—C9—C10—C1	172.01 (18)
O4—N2—C16—C15	168.4 (2)	C1—C11—C12—N1	11.1 (2)
O4—N2—C16—C17	−10.9 (3)	C1—C11—C12—C13	−173.53 (16)
O2—C1—C2—C3	56.9 (2)	C19—C11—C12—N1	−113.37 (18)
C10—C1—C2—C3	−55.0 (2)	C19—C11—C12—C13	62.0 (2)
C11—C1—C2—C3	174.42 (17)	C1—C11—C19—C20	106.3 (2)
O2—C1—C10—O1	97.8 (2)	C1—C11—C19—C24	−74.7 (2)
O2—C1—C10—C9	−80.60 (19)	C12—C11—C19—C20	−139.91 (19)
C2—C1—C10—O1	−147.73 (19)	C12—C11—C19—C24	39.1 (3)
C2—C1—C10—C9	33.9 (2)	N1—C12—C13—C14	−177.13 (18)
C11—C1—C10—O1	−13.5 (3)	N1—C12—C13—C18	3.5 (3)
C11—C1—C10—C9	168.10 (16)	C11—C12—C13—C14	7.7 (3)
O2—C1—C11—C12	−15.17 (16)	C11—C12—C13—C18	−171.68 (18)
O2—C1—C11—C19	105.44 (17)	C12—C13—C14—C15	−177.04 (18)
C2—C1—C11—C12	−134.05 (17)	C18—C13—C14—C15	2.3 (3)
C2—C1—C11—C19	−13.4 (3)	C12—C13—C18—C17	177.39 (19)
C10—C1—C11—C12	95.16 (17)	C14—C13—C18—C17	−2.0 (3)
C10—C1—C11—C19	−144.23 (17)	C13—C14—C15—C16	−0.3 (3)
C1—C2—C3—C4	51.4 (2)	C14—C15—C16—N2	178.49 (19)
C1—C2—C3—C25	180.0 (2)	C14—C15—C16—C17	−2.2 (3)
C2—C3—C4—C5	155.9 (2)	N2—C16—C17—C18	−178.2 (2)
C2—C3—C4—C9	−26.9 (3)	C15—C16—C17—C18	2.6 (3)
C25—C3—C4—C5	29.1 (3)	C16—C17—C18—C13	−0.4 (3)
C25—C3—C4—C9	−153.6 (2)	C11—C19—C20—C21	179.13 (19)
C3—C4—C5—C6	176.3 (2)	C24—C19—C20—C21	0.1 (3)
C9—C4—C5—C6	−1.1 (3)	C11—C19—C24—C23	−179.6 (2)
C3—C4—C9—C8	−175.4 (2)	C20—C19—C24—C23	−0.6 (3)
C3—C4—C9—C10	6.3 (3)	C19—C20—C21—C22	0.3 (3)
C5—C4—C9—C8	2.0 (3)	C20—C21—C22—C23	−0.3 (3)
C5—C4—C9—C10	−176.32 (19)	C21—C22—C23—C24	−0.3 (3)
C4—C5—C6—C7	−0.3 (4)	C22—C23—C24—C19	0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4i	0.99	2.50	3.319 (3)	140
C20—H20···O1ii	0.95	2.58	3.365 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O4i	0.99	2.50	3.319 (3)	140
C20—H20⋯O1ii	0.95	2.58	3.365 (2)	140

Symmetry codes: (i) ; (ii) .