rac-6-Eth-oxy-3,3a,4,9b-tetra-hydro-1,3-diphenyl-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile.

The title compound, C(25)H(22)N(2)O(3), with three stereogenic centres, crystallizes in a centrosymmetric space group as a racemate. The pyran ring adopts a sofa conformation and the five-membered isoxazole ring exhibits an envelope conformation. The dihedral angle between the benzene ring and the mean plane through the near coplanar atoms of the pyran ring is 10.54 (9)°. In the crystal, no significant intermolecular interactions are observed.

Related literature

For the biological activity of the title compound, see: Rozman et al. (2002 ▶); Winn et al. (1976 ▶). For N-atom hybridization, see: Beddoes et al. (1986 ▶). For conformational analysis and puckering parameters, see: Cremer & Pople, (1975 ▶). For related structures, see: Kanchanadevi et al. (2011 ▶); Swaminathan et al. (2012 ▶).

Experimental

Crystal data

C25H22N2O3

M = 398.45

Monoclinic,

a = 15.2994 (9) Å

b = 7.5421 (5) Å

c = 18.7248 (12) Å

β = 107.596 (4)°

V = 2059.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

18432 measured reflections

5109 independent reflections

2805 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.164

S = 1.04

5109 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.18 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶), PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201906X/kp2408sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201906X/kp2408Isup3.hkl

Supplementary material file. DOI: 10.1107/S160053681201906X/kp2408Isup3.cml

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

C25H22N2O3	F(000) = 840
Mr = 398.45	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5109 reflections
a = 15.2994 (9) Å	θ = 1.4–28.3°
b = 7.5421 (5) Å	µ = 0.09 mm−1
c = 18.7248 (12) Å	T = 298 K
β = 107.596 (4)°	Block, colourless
V = 2059.6 (2) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	2805 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Graphite monochromator	θmax = 28.3°, θmin = 1.4°
ω and φ scans	h = −20→20
18432 measured reflections	k = −10→10
5109 independent reflections	l = −20→24

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0749P)2 + 0.2385P] where P = (Fo2 + 2Fc2)/3
5109 reflections	(Δ/σ)max = 0.008
271 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 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	Uiso*/Ueq
O1	0.74167 (9)	0.45965 (16)	0.72376 (7)	0.0602 (4)
O2	0.88519 (9)	−0.03937 (17)	0.68806 (7)	0.0612 (4)
O3	0.59365 (9)	0.65386 (17)	0.67710 (8)	0.0672 (4)
N1	0.81401 (10)	0.0634 (2)	0.63282 (8)	0.0543 (4)
C7	0.74962 (12)	0.0946 (2)	0.67721 (10)	0.0476 (4)
H7	0.7257	−0.0189	0.6887	0.057*
C8	0.81684 (12)	0.1717 (2)	0.74828 (10)	0.0514 (5)
C1	0.67024 (13)	0.3889 (2)	0.66889 (10)	0.0502 (4)
C6	0.67181 (12)	0.2174 (2)	0.64144 (9)	0.0483 (4)
C12	0.94613 (12)	−0.0419 (3)	0.82161 (11)	0.0556 (5)
C11	0.90766 (13)	0.0711 (3)	0.75323 (11)	0.0561 (5)
H11	0.9542	0.1573	0.7500	0.067*
C20	0.77892 (12)	−0.0486 (3)	0.56829 (11)	0.0548 (5)
C9	0.82649 (14)	0.3691 (2)	0.73450 (11)	0.0600 (5)
H9A	0.8727	0.4202	0.7770	0.072*
H9B	0.8466	0.3845	0.6905	0.072*
C2	0.59079 (13)	0.4927 (2)	0.64301 (10)	0.0542 (5)
C5	0.59528 (13)	0.1560 (3)	0.58543 (10)	0.0568 (5)
H5	0.5957	0.0426	0.5660	0.068*
C17	1.02141 (13)	0.0150 (3)	0.87856 (12)	0.0701 (6)
H17	1.0493	0.1221	0.8738	0.084*
C10	0.78370 (14)	0.1491 (3)	0.81384 (11)	0.0583 (5)
C3	0.51685 (14)	0.4285 (3)	0.58771 (11)	0.0620 (5)
H3	0.4646	0.4981	0.5695	0.074*
C18	0.50900 (15)	0.7498 (3)	0.66297 (12)	0.0695 (6)
H18A	0.4604	0.6702	0.6658	0.083*
H18B	0.4922	0.8014	0.6132	0.083*
C21	0.75973 (14)	0.0310 (3)	0.49899 (12)	0.0689 (6)
H21	0.7702	0.1517	0.4956	0.083*
C4	0.51968 (14)	0.2608 (3)	0.55889 (11)	0.0645 (5)
H4	0.4695	0.2189	0.5209	0.077*
N2	0.75559 (15)	0.1391 (3)	0.86341 (11)	0.0825 (6)
C13	0.90569 (15)	−0.2018 (3)	0.83037 (13)	0.0706 (6)
H13	0.8547	−0.2422	0.7928	0.085*
C24	0.72930 (16)	−0.3275 (3)	0.50900 (16)	0.0823 (7)
H24	0.7191	−0.4485	0.5120	0.099*
C25	0.76250 (14)	−0.2284 (3)	0.57391 (13)	0.0674 (6)
H25	0.7736	−0.2816	0.6206	0.081*
C14	0.94057 (18)	−0.3005 (3)	0.89414 (14)	0.0833 (7)
H14	0.9130	−0.4073	0.8997	0.100*
C23	0.71127 (16)	−0.2466 (4)	0.43976 (15)	0.0866 (8)
H23	0.6897	−0.3139	0.3964	0.104*
C22	0.72498 (16)	−0.0680 (4)	0.43459 (13)	0.0818 (7)
H22	0.7109	−0.0137	0.3879	0.098*
C19	0.52145 (18)	0.8905 (3)	0.71959 (13)	0.0847 (7)
H19A	0.4654	0.9562	0.7107	0.127*
H19B	0.5696	0.9688	0.7164	0.127*
H19C	0.5374	0.8383	0.7686	0.127*
C15	1.01620 (18)	−0.2420 (4)	0.94988 (14)	0.0872 (7)
H15	1.0403	−0.3102	0.9927	0.105*
C16	1.05552 (16)	−0.0852 (4)	0.94225 (14)	0.0865 (7)
H16	1.1060	−0.0449	0.9804	0.104*

	U11	U22	U33	U12	U13	U23
O1	0.0672 (8)	0.0368 (7)	0.0725 (8)	0.0015 (7)	0.0151 (7)	−0.0087 (6)
O2	0.0582 (7)	0.0561 (8)	0.0708 (8)	0.0089 (7)	0.0220 (6)	−0.0094 (7)
O3	0.0757 (9)	0.0444 (8)	0.0851 (9)	0.0107 (7)	0.0299 (7)	−0.0058 (7)
N1	0.0549 (9)	0.0488 (9)	0.0627 (9)	−0.0006 (8)	0.0231 (7)	−0.0060 (8)
C7	0.0520 (10)	0.0342 (9)	0.0616 (10)	−0.0033 (8)	0.0244 (8)	−0.0045 (8)
C8	0.0555 (10)	0.0395 (10)	0.0610 (10)	0.0004 (9)	0.0204 (8)	−0.0017 (8)
C1	0.0605 (11)	0.0397 (10)	0.0534 (10)	−0.0001 (9)	0.0218 (9)	−0.0007 (8)
C6	0.0554 (10)	0.0399 (10)	0.0545 (10)	−0.0027 (9)	0.0240 (8)	−0.0013 (8)
C12	0.0487 (10)	0.0470 (11)	0.0731 (12)	0.0038 (9)	0.0214 (9)	−0.0080 (10)
C11	0.0546 (11)	0.0458 (11)	0.0710 (12)	−0.0044 (9)	0.0238 (9)	−0.0098 (10)
C20	0.0519 (10)	0.0526 (12)	0.0648 (11)	0.0029 (9)	0.0251 (9)	−0.0079 (10)
C9	0.0638 (12)	0.0409 (11)	0.0730 (12)	−0.0069 (10)	0.0176 (10)	−0.0079 (9)
C2	0.0712 (12)	0.0392 (10)	0.0593 (10)	0.0030 (10)	0.0305 (10)	0.0009 (9)
C5	0.0623 (12)	0.0500 (11)	0.0601 (11)	−0.0002 (10)	0.0215 (9)	−0.0089 (9)
C17	0.0510 (11)	0.0743 (15)	0.0850 (15)	0.0001 (11)	0.0207 (11)	−0.0111 (13)
C10	0.0663 (12)	0.0445 (11)	0.0633 (12)	0.0067 (10)	0.0185 (10)	−0.0027 (10)
C3	0.0659 (12)	0.0612 (13)	0.0592 (11)	0.0117 (11)	0.0195 (10)	0.0024 (10)
C18	0.0842 (15)	0.0556 (13)	0.0758 (13)	0.0181 (12)	0.0346 (11)	0.0065 (11)
C21	0.0695 (13)	0.0741 (15)	0.0702 (13)	−0.0071 (12)	0.0318 (11)	−0.0062 (12)
C4	0.0642 (12)	0.0679 (14)	0.0581 (11)	0.0047 (11)	0.0135 (9)	−0.0080 (10)
N2	0.1075 (15)	0.0767 (14)	0.0739 (12)	0.0162 (12)	0.0432 (11)	0.0031 (10)
C13	0.0691 (13)	0.0496 (13)	0.0844 (15)	0.0020 (11)	0.0100 (11)	−0.0020 (11)
C24	0.0709 (14)	0.0604 (14)	0.1057 (19)	0.0073 (12)	0.0118 (13)	−0.0213 (14)
C25	0.0668 (13)	0.0516 (12)	0.0803 (13)	0.0061 (11)	0.0170 (10)	−0.0087 (11)
C14	0.0882 (17)	0.0614 (14)	0.0978 (17)	0.0092 (13)	0.0241 (14)	0.0120 (13)
C23	0.0663 (14)	0.105 (2)	0.0869 (18)	0.0002 (15)	0.0207 (12)	−0.0399 (17)
C22	0.0761 (15)	0.105 (2)	0.0679 (14)	−0.0043 (15)	0.0270 (11)	−0.0103 (14)
C19	0.1040 (18)	0.0717 (15)	0.0895 (16)	0.0167 (14)	0.0460 (14)	−0.0053 (13)
C15	0.0762 (16)	0.093 (2)	0.0865 (17)	0.0249 (16)	0.0158 (13)	0.0133 (15)
C16	0.0588 (13)	0.110 (2)	0.0824 (16)	0.0111 (15)	0.0096 (12)	−0.0049 (16)

O1—C1	1.362 (2)	C17—C16	1.375 (3)
O1—C9	1.426 (2)	C17—H17	0.9300
O2—C11	1.431 (2)	C10—N2	1.137 (2)
O2—N1	1.4748 (19)	C3—C4	1.381 (3)
O3—C2	1.368 (2)	C3—H3	0.9300
O3—C18	1.437 (2)	C18—C19	1.471 (3)
N1—C20	1.438 (2)	C18—H18A	0.9700
N1—C7	1.487 (2)	C18—H18B	0.9700
C7—C6	1.497 (2)	C21—C22	1.381 (3)
C7—C8	1.529 (2)	C21—H21	0.9300
C7—H7	0.9800	C4—H4	0.9300
C8—C10	1.473 (3)	C13—C14	1.371 (3)
C8—C9	1.526 (3)	C13—H13	0.9300
C8—C11	1.561 (3)	C24—C23	1.383 (4)
C1—C6	1.395 (2)	C24—C25	1.386 (3)
C1—C2	1.403 (3)	C24—H24	0.9300
C6—C5	1.394 (2)	C25—H25	0.9300
C12—C17	1.380 (3)	C14—C15	1.376 (3)
C12—C13	1.388 (3)	C14—H14	0.9300
C12—C11	1.502 (3)	C23—C22	1.371 (4)
C11—H11	0.9800	C23—H23	0.9300
C20—C21	1.378 (3)	C22—H22	0.9300
C20—C25	1.389 (3)	C19—H19A	0.9600
C9—H9A	0.9700	C19—H19B	0.9600
C9—H9B	0.9700	C19—H19C	0.9600
C2—C3	1.370 (3)	C15—C16	1.354 (4)
C5—C4	1.365 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C1—O1—C9	114.04 (14)	C16—C17—H17	119.7
C11—O2—N1	103.20 (12)	C12—C17—H17	119.7
C2—O3—C18	117.52 (16)	N2—C10—C8	176.6 (2)
C20—N1—O2	106.84 (13)	C2—C3—C4	120.16 (19)
C20—N1—C7	114.86 (14)	C2—C3—H3	119.9
O2—N1—C7	99.47 (12)	C4—C3—H3	119.9
N1—C7—C6	114.78 (14)	O3—C18—C19	108.52 (18)
N1—C7—C8	99.30 (13)	O3—C18—H18A	110.0
C6—C7—C8	112.86 (14)	C19—C18—H18A	110.0
N1—C7—H7	109.8	O3—C18—H18B	110.0
C6—C7—H7	109.8	C19—C18—H18B	110.0
C8—C7—H7	109.8	H18A—C18—H18B	108.4
C10—C8—C9	109.21 (15)	C20—C21—C22	120.2 (2)
C10—C8—C7	111.77 (15)	C20—C21—H21	119.9
C9—C8—C7	107.33 (15)	C22—C21—H21	119.9
C10—C8—C11	114.76 (15)	C5—C4—C3	120.78 (19)
C9—C8—C11	110.76 (15)	C5—C4—H4	119.6
C7—C8—C11	102.66 (14)	C3—C4—H4	119.6
O1—C1—C6	122.82 (16)	C14—C13—C12	120.3 (2)
O1—C1—C2	117.10 (16)	C14—C13—H13	119.8
C6—C1—C2	119.98 (17)	C12—C13—H13	119.8
C5—C6—C1	118.78 (17)	C23—C24—C25	120.0 (2)
C5—C6—C7	120.29 (16)	C23—C24—H24	120.0
C1—C6—C7	120.58 (16)	C25—C24—H24	120.0
C17—C12—C13	118.5 (2)	C24—C25—C20	119.1 (2)
C17—C12—C11	120.17 (19)	C24—C25—H25	120.4
C13—C12—C11	121.32 (18)	C20—C25—H25	120.4
O2—C11—C12	109.16 (15)	C13—C14—C15	120.2 (2)
O2—C11—C8	104.61 (14)	C13—C14—H14	119.9
C12—C11—C8	116.01 (15)	C15—C14—H14	119.9
O2—C11—H11	108.9	C22—C23—C24	120.5 (2)
C12—C11—H11	108.9	C22—C23—H23	119.7
C8—C11—H11	108.9	C24—C23—H23	119.7
C21—C20—C25	120.29 (19)	C23—C22—C21	119.7 (2)
C21—C20—N1	117.04 (18)	C23—C22—H22	120.1
C25—C20—N1	122.65 (18)	C21—C22—H22	120.1
O1—C9—C8	111.13 (15)	C18—C19—H19A	109.5
O1—C9—H9A	109.4	C18—C19—H19B	109.5
C8—C9—H9A	109.4	H19A—C19—H19B	109.5
O1—C9—H9B	109.4	C18—C19—H19C	109.5
C8—C9—H9B	109.4	H19A—C19—H19C	109.5
H9A—C9—H9B	108.0	H19B—C19—H19C	109.5
O3—C2—C3	124.70 (18)	C16—C15—C14	119.9 (2)
O3—C2—C1	115.63 (17)	C16—C15—H15	120.0
C3—C2—C1	119.67 (17)	C14—C15—H15	120.0
C4—C5—C6	120.53 (18)	C15—C16—C17	120.5 (2)
C4—C5—H5	119.7	C15—C16—H16	119.7
C6—C5—H5	119.7	C17—C16—H16	119.7
C16—C17—C12	120.6 (2)
C11—O2—N1—C20	−172.76 (14)	O2—N1—C20—C25	40.8 (2)
C11—O2—N1—C7	−53.05 (15)	C7—N1—C20—C25	−68.5 (2)
C20—N1—C7—C6	−73.56 (19)	C1—O1—C9—C8	−54.2 (2)
O2—N1—C7—C6	172.81 (13)	C10—C8—C9—O1	−57.5 (2)
C20—N1—C7—C8	165.83 (15)	C7—C8—C9—O1	63.88 (19)
O2—N1—C7—C8	52.20 (14)	C11—C8—C9—O1	175.21 (14)
N1—C7—C8—C10	−156.53 (15)	C18—O3—C2—C3	10.7 (3)
C6—C7—C8—C10	81.46 (18)	C18—O3—C2—C1	−168.42 (16)
N1—C7—C8—C9	83.74 (16)	O1—C1—C2—O3	−1.0 (2)
C6—C7—C8—C9	−38.3 (2)	C6—C1—C2—O3	175.48 (15)
N1—C7—C8—C11	−33.04 (16)	O1—C1—C2—C3	179.81 (16)
C6—C7—C8—C11	−155.05 (14)	C6—C1—C2—C3	−3.7 (3)
C9—O1—C1—C6	18.2 (2)	C1—C6—C5—C4	−1.1 (3)
C9—O1—C1—C2	−165.40 (15)	C7—C6—C5—C4	172.18 (17)
O1—C1—C6—C5	179.70 (16)	C13—C12—C17—C16	0.3 (3)
C2—C1—C6—C5	3.4 (3)	C11—C12—C17—C16	178.19 (19)
O1—C1—C6—C7	6.5 (3)	O3—C2—C3—C4	−177.50 (18)
C2—C1—C6—C7	−169.83 (15)	C1—C2—C3—C4	1.6 (3)
N1—C7—C6—C5	80.0 (2)	C2—O3—C18—C19	164.34 (17)
C8—C7—C6—C5	−167.23 (16)	C25—C20—C21—C22	−0.7 (3)
N1—C7—C6—C1	−106.92 (18)	N1—C20—C21—C22	−179.33 (18)
C8—C7—C6—C1	5.9 (2)	C6—C5—C4—C3	−1.0 (3)
N1—O2—C11—C12	155.50 (14)	C2—C3—C4—C5	0.8 (3)
N1—O2—C11—C8	30.73 (17)	C17—C12—C13—C14	−0.4 (3)
C17—C12—C11—O2	137.73 (18)	C11—C12—C13—C14	−178.3 (2)
C13—C12—C11—O2	−44.4 (2)	C23—C24—C25—C20	−1.2 (3)
C17—C12—C11—C8	−104.5 (2)	C21—C20—C25—C24	2.0 (3)
C13—C12—C11—C8	73.4 (2)	N1—C20—C25—C24	−179.50 (18)
C10—C8—C11—O2	123.37 (17)	C12—C13—C14—C15	−0.2 (4)
C9—C8—C11—O2	−112.41 (17)	C25—C24—C23—C22	−0.7 (4)
C7—C8—C11—O2	1.90 (18)	C24—C23—C22—C21	2.0 (4)
C10—C8—C11—C12	3.1 (2)	C20—C21—C22—C23	−1.3 (3)
C9—C8—C11—C12	127.29 (17)	C13—C14—C15—C16	1.0 (4)
C7—C8—C11—C12	−118.40 (17)	C14—C15—C16—C17	−1.1 (4)
O2—N1—C20—C21	−140.65 (17)	C12—C17—C16—C15	0.5 (3)
C7—N1—C20—C21	110.10 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N1	0.97	2.64	2.960 (2)	100
C25—H25···O1i	0.93	2.89	3.748 (3)	154
C23—H23···N2ii	0.93	2.79	3.443 (3)	128