(2-tert-Butyl-3-phenyl-2,3-di-hydro-isoxazole-4,5-di-yl)bis-(phenyl-methanone).

The phenyl and tert-butyl groups of the title compound, C27H25NO3, exhibit a trans configuration in agreement with the stereochemistry of the Z phenyl-N-tert-butyl-nitrone starting material. The attached carbonyl groups are not coplanar with the neighboring di-hydro-isoxazole ring and the phenyl rings they are bonded to, with torsion angles of 59.26 (8), 17.53 (11), 16.52 (12) and 52.86 (7)°. The dihedral angle between the di-hydro-isoxazole ring and the directly attached phenyl group is 86.86 (8)°. There are two nonclassical inter-molecular C-H⋯O hydrogen-bonding inter-actions that operate together with an inter-molecular C-H⋯π inter-action to form a supramolecular architecture in the crystal system.

Related literature

For background to isoxazoline derivatives and their applications, see: Kiss et al. (2009 ▶); Velikorodov & Sukhenko (2003 ▶); Shi et al. (2012 ▶); Khan & Lee (2006 ▶). For the mechanism of the 1,3-dipolar cyclo­addition of nitro­nes with alkynes, see: Eberson et al. (1998 ▶). For the synthesis of related compounds, see: Chakraborty et al. (2012 ▶).

Experimental

Crystal data

C27H25NO3

M = 411.48

Orthorhombic,

a = 20.1034 (12) Å

b = 17.799 (1) Å

c = 6.1366 (3) Å

V = 2195.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.968, T max = 0.984

20181 measured reflections

2967 independent reflections

2422 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.094

S = 1.05

2967 reflections

283 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019508/zl2560sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019508/zl2560Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019508/zl2560Isup3.cml

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

C27H25NO3	F(000) = 872
Mr = 411.48	Dx = 1.245 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8059 reflections
a = 20.1034 (12) Å	θ = 2.3–25.1°
b = 17.799 (1) Å	µ = 0.08 mm−1
c = 6.1366 (3) Å	T = 296 K
V = 2195.8 (2) Å3	Block, yellow
Z = 4	0.40 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	2967 independent reflections
Radiation source: fine-focus sealed tube	2422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.33 pixels mm-1	θmax = 28.3°, θmin = 3.1°
ω and φ scan	h = −26→24
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −23→20
Tmin = 0.968, Tmax = 0.984	l = −8→8
20181 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0417P)2 + 0.2966P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.11 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.14603 (9)	0.40278 (10)	0.0012 (3)	0.0661 (5)
O2	0.05003 (7)	0.36111 (8)	0.3046 (3)	0.0517 (4)
O3	0.20313 (8)	0.27030 (9)	0.7795 (3)	0.0616 (4)
N1	0.01783 (8)	0.30875 (9)	0.4612 (3)	0.0458 (4)
C3	0.25597 (12)	0.60359 (13)	0.4233 (5)	0.0625 (7)
H3	0.2772	0.6473	0.4690	0.075*
C2	0.26649 (13)	0.57720 (14)	0.2177 (5)	0.0637 (7)
H2	0.2956	0.6023	0.1250	0.076*
C1	0.23438 (11)	0.51380 (13)	0.1469 (4)	0.0545 (5)
H1	0.2416	0.4962	0.0062	0.065*
C6	0.19103 (9)	0.47575 (10)	0.2851 (3)	0.0402 (4)
C7	0.15240 (10)	0.41275 (12)	0.1949 (4)	0.0446 (5)
C8	0.11570 (9)	0.36106 (10)	0.3468 (3)	0.0407 (4)
C9	0.13418 (9)	0.31458 (10)	0.5061 (3)	0.0398 (4)
C17	0.07315 (9)	0.27504 (10)	0.5896 (4)	0.0432 (4)
H17	0.0670	0.2856	0.7451	0.052*
C18	0.07424 (9)	0.19093 (11)	0.5505 (4)	0.0456 (5)
C23	0.09136 (13)	0.16269 (13)	0.3489 (4)	0.0619 (6)
H23	0.1022	0.1956	0.2367	0.074*
C22	0.09257 (16)	0.08604 (14)	0.3114 (5)	0.0763 (8)
H22	0.1048	0.0677	0.1752	0.092*
C21	0.07586 (14)	0.03747 (13)	0.4739 (6)	0.0761 (8)
H21	0.0765	−0.0140	0.4486	0.091*
C24	−0.03126 (10)	0.35530 (11)	0.5852 (4)	0.0510 (5)
C26	−0.06460 (13)	0.30225 (15)	0.7463 (5)	0.0782 (9)
H26A	−0.0784	0.2575	0.6717	0.117*
H26B	−0.1027	0.3265	0.8091	0.117*
H26C	−0.0337	0.2893	0.8595	0.117*
C27	−0.08187 (12)	0.38226 (15)	0.4187 (5)	0.0708 (7)
H27A	−0.0603	0.4140	0.3139	0.106*
H27B	−0.1163	0.4100	0.4912	0.106*
H27C	−0.1010	0.3397	0.3457	0.106*
C25	−0.00051 (13)	0.42144 (13)	0.7032 (5)	0.0639 (6)
H25A	0.0318	0.4036	0.8061	0.096*
H25B	−0.0346	0.4488	0.7788	0.096*
H25C	0.0208	0.4539	0.5996	0.096*
C20	0.05818 (14)	0.06446 (14)	0.6739 (6)	0.0737 (8)
H20	0.0466	0.0312	0.7845	0.088*
C19	0.05747 (11)	0.14130 (13)	0.7128 (5)	0.0595 (6)
H19	0.0456	0.1593	0.8497	0.071*
C10	0.19933 (10)	0.30137 (10)	0.6033 (4)	0.0438 (4)
C11	0.26076 (9)	0.32369 (10)	0.4850 (4)	0.0451 (5)
C16	0.30928 (11)	0.36438 (13)	0.5935 (5)	0.0619 (6)
H16	0.3019	0.3810	0.7351	0.074*
C15	0.36829 (14)	0.37991 (17)	0.4906 (7)	0.0864 (10)
H15	0.4003	0.4087	0.5612	0.104*
C14	0.38057 (15)	0.35349 (19)	0.2856 (8)	0.0933 (11)
H14	0.4213	0.3629	0.2193	0.112*
C13	0.33269 (16)	0.31311 (17)	0.1776 (5)	0.0814 (9)
H13	0.3410	0.2951	0.0380	0.098*
C12	0.27250 (12)	0.29918 (13)	0.2752 (4)	0.0576 (6)
H12	0.2396	0.2732	0.1998	0.069*
C5	0.18161 (10)	0.50193 (11)	0.4950 (4)	0.0462 (4)
H5	0.1534	0.4764	0.5897	0.055*
C4	0.21427 (12)	0.56621 (12)	0.5637 (4)	0.0560 (5)
H4	0.2080	0.5840	0.7047	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0854 (12)	0.0756 (10)	0.0372 (8)	−0.0054 (9)	−0.0025 (8)	−0.0026 (8)
O2	0.0428 (7)	0.0611 (8)	0.0511 (8)	0.0062 (6)	−0.0059 (7)	0.0124 (7)
O3	0.0648 (9)	0.0699 (10)	0.0502 (9)	0.0031 (7)	−0.0153 (8)	0.0129 (8)
N1	0.0422 (8)	0.0427 (8)	0.0526 (10)	0.0021 (7)	−0.0033 (8)	0.0006 (8)
C3	0.0596 (14)	0.0528 (12)	0.0750 (18)	−0.0103 (10)	0.0015 (13)	0.0032 (13)
C2	0.0545 (13)	0.0655 (14)	0.0711 (17)	−0.0108 (11)	0.0147 (12)	0.0140 (13)
C1	0.0516 (12)	0.0644 (13)	0.0475 (12)	0.0049 (10)	0.0121 (10)	0.0053 (10)
C6	0.0397 (9)	0.0416 (9)	0.0393 (10)	0.0089 (7)	0.0017 (9)	0.0072 (8)
C7	0.0485 (11)	0.0460 (10)	0.0394 (11)	0.0100 (8)	−0.0002 (9)	0.0031 (9)
C8	0.0419 (10)	0.0406 (10)	0.0398 (11)	0.0025 (8)	−0.0046 (8)	−0.0043 (8)
C9	0.0437 (9)	0.0364 (8)	0.0393 (10)	−0.0005 (7)	−0.0060 (9)	−0.0032 (8)
C17	0.0467 (10)	0.0427 (10)	0.0402 (10)	0.0024 (8)	−0.0020 (9)	0.0009 (9)
C18	0.0425 (10)	0.0397 (9)	0.0544 (13)	−0.0026 (8)	−0.0094 (9)	0.0057 (9)
C23	0.0876 (17)	0.0436 (11)	0.0546 (15)	−0.0034 (11)	−0.0131 (13)	0.0018 (11)
C22	0.109 (2)	0.0506 (13)	0.0698 (17)	−0.0003 (14)	−0.0221 (17)	−0.0089 (13)
C21	0.0867 (18)	0.0427 (12)	0.099 (2)	−0.0096 (12)	−0.0261 (18)	0.0003 (15)
C24	0.0430 (10)	0.0489 (11)	0.0611 (13)	0.0021 (9)	0.0018 (10)	−0.0082 (11)
C26	0.0658 (15)	0.0703 (15)	0.098 (2)	−0.0048 (12)	0.0304 (16)	−0.0025 (16)
C27	0.0476 (12)	0.0747 (15)	0.090 (2)	0.0146 (11)	−0.0092 (13)	−0.0145 (16)
C25	0.0631 (14)	0.0559 (13)	0.0727 (17)	0.0017 (11)	−0.0043 (13)	−0.0172 (13)
C20	0.0683 (15)	0.0519 (14)	0.101 (2)	−0.0095 (12)	−0.0033 (16)	0.0288 (15)
C19	0.0527 (12)	0.0575 (13)	0.0684 (16)	−0.0018 (10)	0.0030 (11)	0.0151 (12)
C10	0.0524 (11)	0.0374 (9)	0.0415 (10)	0.0045 (8)	−0.0131 (9)	−0.0050 (9)
C11	0.0434 (10)	0.0399 (10)	0.0520 (12)	0.0079 (8)	−0.0102 (10)	0.0036 (9)
C16	0.0570 (13)	0.0583 (13)	0.0704 (16)	−0.0015 (10)	−0.0167 (13)	0.0024 (13)
C15	0.0545 (15)	0.0826 (19)	0.122 (3)	−0.0141 (13)	−0.0181 (19)	0.025 (2)
C14	0.0583 (16)	0.098 (2)	0.123 (3)	0.0151 (16)	0.018 (2)	0.045 (2)
C13	0.0803 (19)	0.0897 (19)	0.0742 (19)	0.0328 (16)	0.0175 (16)	0.0174 (16)
C12	0.0582 (13)	0.0591 (13)	0.0556 (14)	0.0142 (10)	−0.0043 (11)	−0.0019 (11)
C5	0.0490 (11)	0.0467 (10)	0.0428 (10)	−0.0020 (8)	0.0056 (10)	0.0041 (10)
C4	0.0655 (13)	0.0510 (11)	0.0513 (13)	−0.0036 (10)	0.0040 (11)	−0.0052 (10)

O1—C7	1.209 (3)	C24—C27	1.520 (4)
O2—C8	1.345 (2)	C24—C26	1.522 (3)
O2—N1	1.487 (2)	C26—H26A	0.9600
O3—C10	1.217 (3)	C26—H26B	0.9600
N1—C17	1.489 (2)	C26—H26C	0.9600
N1—C24	1.496 (3)	C27—H27A	0.9600
C3—C2	1.363 (4)	C27—H27B	0.9600
C3—C4	1.374 (3)	C27—H27C	0.9600
C3—H3	0.9300	C25—H25A	0.9600
C2—C1	1.371 (3)	C25—H25B	0.9600
C2—H2	0.9300	C25—H25C	0.9600
C1—C6	1.392 (3)	C20—C19	1.388 (4)
C1—H1	0.9300	C20—H20	0.9300
C6—C5	1.383 (3)	C19—H19	0.9300
C6—C7	1.472 (3)	C10—C11	1.486 (3)
C7—C8	1.503 (3)	C11—C12	1.380 (3)
C8—C9	1.333 (3)	C11—C16	1.386 (3)
C9—C10	1.458 (3)	C16—C15	1.372 (4)
C9—C17	1.505 (3)	C16—H16	0.9300
C17—C18	1.516 (3)	C15—C14	1.365 (5)
C17—H17	0.9800	C15—H15	0.9300
C18—C19	1.374 (3)	C14—C13	1.372 (5)
C18—C23	1.379 (3)	C14—H14	0.9300
C23—C22	1.384 (3)	C13—C12	1.372 (4)
C23—H23	0.9300	C13—H13	0.9300
C22—C21	1.362 (4)	C12—H12	0.9300
C22—H22	0.9300	C5—C4	1.385 (3)
C21—C20	1.365 (5)	C5—H5	0.9300
C21—H21	0.9300	C4—H4	0.9300
C24—C25	1.514 (3)
C8—O2—N1	107.60 (14)	C24—C26—H26B	109.5
O2—N1—C17	105.62 (13)	H26A—C26—H26B	109.5
O2—N1—C24	105.59 (14)	C24—C26—H26C	109.5
C17—N1—C24	116.51 (17)	H26A—C26—H26C	109.5
C2—C3—C4	120.6 (2)	H26B—C26—H26C	109.5
C2—C3—H3	119.7	C24—C27—H27A	109.5
C4—C3—H3	119.7	C24—C27—H27B	109.5
C3—C2—C1	120.3 (2)	H27A—C27—H27B	109.5
C3—C2—H2	119.9	C24—C27—H27C	109.5
C1—C2—H2	119.9	H27A—C27—H27C	109.5
C2—C1—C6	120.1 (2)	H27B—C27—H27C	109.5
C2—C1—H1	119.9	C24—C25—H25A	109.5
C6—C1—H1	119.9	C24—C25—H25B	109.5
C5—C6—C1	119.32 (19)	H25A—C25—H25B	109.5
C5—C6—C7	122.32 (18)	C24—C25—H25C	109.5
C1—C6—C7	118.14 (19)	H25A—C25—H25C	109.5
O1—C7—C6	122.5 (2)	H25B—C25—H25C	109.5
O1—C7—C8	117.9 (2)	C21—C20—C19	120.3 (3)
C6—C7—C8	119.47 (18)	C21—C20—H20	119.9
C9—C8—O2	114.52 (17)	C19—C20—H20	119.9
C9—C8—C7	134.23 (18)	C18—C19—C20	120.4 (3)
O2—C8—C7	111.20 (16)	C18—C19—H19	119.8
C8—C9—C10	130.56 (18)	C20—C19—H19	119.8
C8—C9—C17	108.23 (16)	O3—C10—C9	119.5 (2)
C10—C9—C17	121.17 (17)	O3—C10—C11	120.21 (18)
N1—C17—C9	103.90 (15)	C9—C10—C11	120.22 (18)
N1—C17—C18	108.96 (15)	C12—C11—C16	119.6 (2)
C9—C17—C18	113.33 (16)	C12—C11—C10	120.88 (19)
N1—C17—H17	110.2	C16—C11—C10	119.3 (2)
C9—C17—H17	110.2	C15—C16—C11	119.5 (3)
C18—C17—H17	110.2	C15—C16—H16	120.2
C19—C18—C23	118.5 (2)	C11—C16—H16	120.2
C19—C18—C17	121.1 (2)	C14—C15—C16	120.7 (3)
C23—C18—C17	120.37 (19)	C14—C15—H15	119.6
C18—C23—C22	120.9 (2)	C16—C15—H15	119.6
C18—C23—H23	119.6	C15—C14—C13	119.9 (3)
C22—C23—H23	119.6	C15—C14—H14	120.1
C21—C22—C23	120.0 (3)	C13—C14—H14	120.1
C21—C22—H22	120.0	C14—C13—C12	120.2 (3)
C23—C22—H22	120.0	C14—C13—H13	119.9
C22—C21—C20	119.9 (2)	C12—C13—H13	119.9
C22—C21—H21	120.0	C13—C12—C11	120.0 (3)
C20—C21—H21	120.0	C13—C12—H12	120.0
N1—C24—C25	113.87 (17)	C11—C12—H12	120.0
N1—C24—C27	105.9 (2)	C6—C5—C4	119.8 (2)
C25—C24—C27	110.46 (19)	C6—C5—H5	120.1
N1—C24—C26	106.08 (17)	C4—C5—H5	120.1
C25—C24—C26	110.6 (2)	C3—C4—C5	119.9 (2)
C27—C24—C26	109.7 (2)	C3—C4—H4	120.1
C24—C26—H26A	109.5	C5—C4—H4	120.1
C8—O2—N1—C17	−3.35 (19)	C17—C18—C23—C22	180.0 (2)
C8—O2—N1—C24	120.65 (17)	C18—C23—C22—C21	0.9 (4)
C4—C3—C2—C1	1.4 (4)	C23—C22—C21—C20	−0.2 (5)
C3—C2—C1—C6	−0.3 (4)	O2—N1—C24—C25	−58.2 (2)
C2—C1—C6—C5	−1.0 (3)	C17—N1—C24—C25	58.7 (2)
C2—C1—C6—C7	173.7 (2)	O2—N1—C24—C27	63.41 (19)
C5—C6—C7—O1	158.6 (2)	C17—N1—C24—C27	−179.74 (18)
C1—C6—C7—O1	−15.9 (3)	O2—N1—C24—C26	179.99 (18)
C5—C6—C7—C8	−17.5 (3)	C17—N1—C24—C26	−63.2 (2)
C1—C6—C7—C8	167.99 (18)	C22—C21—C20—C19	−0.3 (4)
N1—O2—C8—C9	1.9 (2)	C23—C18—C19—C20	0.3 (3)
N1—O2—C8—C7	179.93 (15)	C17—C18—C19—C20	179.5 (2)
O1—C7—C8—C9	121.7 (3)	C21—C20—C19—C18	0.3 (4)
C6—C7—C8—C9	−62.0 (3)	C8—C9—C10—O3	162.4 (2)
O1—C7—C8—O2	−55.8 (3)	C17—C9—C10—O3	−14.9 (3)
C6—C7—C8—O2	120.48 (19)	C8—C9—C10—C11	−19.3 (3)
O2—C8—C9—C10	−177.13 (19)	C17—C9—C10—C11	163.36 (17)
C7—C8—C9—C10	5.4 (4)	O3—C10—C11—C12	124.2 (2)
O2—C8—C9—C17	0.4 (2)	C9—C10—C11—C12	−54.0 (2)
C7—C8—C9—C17	−177.0 (2)	O3—C10—C11—C16	−50.4 (3)
O2—N1—C17—C9	3.45 (18)	C9—C10—C11—C16	131.4 (2)
C24—N1—C17—C9	−113.39 (17)	C12—C11—C16—C15	0.2 (3)
O2—N1—C17—C18	−117.64 (17)	C10—C11—C16—C15	174.8 (2)
C24—N1—C17—C18	125.52 (18)	C11—C16—C15—C14	−2.3 (4)
C8—C9—C17—N1	−2.5 (2)	C16—C15—C14—C13	2.2 (5)
C10—C9—C17—N1	175.33 (17)	C15—C14—C13—C12	0.0 (4)
C8—C9—C17—C18	115.60 (19)	C14—C13—C12—C11	−2.1 (4)
C10—C9—C17—C18	−66.6 (2)	C16—C11—C12—C13	2.0 (3)
N1—C17—C18—C19	−111.1 (2)	C10—C11—C12—C13	−172.5 (2)
C9—C17—C18—C19	133.7 (2)	C1—C6—C5—C4	1.2 (3)
N1—C17—C18—C23	68.0 (2)	C7—C6—C5—C4	−173.24 (19)
C9—C17—C18—C23	−47.1 (3)	C2—C3—C4—C5	−1.2 (4)
C19—C18—C23—C22	−0.9 (4)	C6—C5—C4—C3	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.51	3.203 (3)	131
C25—H25A···O1ii	0.96	2.59	3.483 (3)	155
C2—H2···Cg1i	0.93	2.70	3.490 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.51	3.203 (3)	131
C25—H25A⋯O1ii	0.96	2.59	3.483 (3)	155
C2—H2⋯Cg1i	0.93	2.70	3.490 (3)	143

Symmetry codes: (i) ; (ii) .