rac-Methyl 3-(2-meth-oxy-phen-yl)-1-phenyl-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carboxyl-ate.

The title compound, C(25)H(23)NO(5), comprising two stereogenic carbon atoms of the same configuration, crystallizes in a centrosymmetric space group as a racemate. The six-membered pyran ring and the five-membered isoxazole ring adopt sofa and twisted conformations, respectively. The dihedral angle between the benzene ring and the mean plane through the near coplanar atoms of the pyran ring is 10.73 (7)°. The crystal structure features C-H⋯O hydrogen bonds.

Related literature

For the biological activity of the title compound, see: Eddington et al. (2002 ▶); Mullen et al. (1988 ▶); Kashiwada et al. (2001 ▶); Caine (1993 ▶). For N-atom hybridization, see: Beddoes et al. (1986 ▶). For related structures, see: Kanchanadevi et al. (2011 ▶); Swaminathan et al. (2012 ▶). For conformational analysis and puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C25H23NO5

M = 417.44

Monoclinic,

a = 18.3791 (7) Å

b = 15.2466 (6) Å

c = 7.7235 (3) Å

β = 90.514 (2)°

V = 2164.18 (15) 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

20989 measured reflections

5478 independent reflections

3614 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.159

S = 0.96

5478 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.16 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/S1600536812021356/kp2411sup1.cif

Structure factors: contains datablock(s) guru2. DOI: 10.1107/S1600536812021356/kp2411Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021356/kp2411Isup3.cml

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

C25H23NO5	F(000) = 880
Mr = 417.44	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5478 reflections
a = 18.3791 (7) Å	θ = 1.7–28.6°
b = 15.2466 (6) Å	µ = 0.09 mm−1
c = 7.7235 (3) Å	T = 298 K
β = 90.514 (2)°	Block, colourless
V = 2164.18 (15) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3614 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 28.6°, θmin = 1.7°
ω and φ scans	h = −23→24
20989 measured reflections	k = −20→17
5478 independent reflections	l = −10→10

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.7112P] where P = (Fo2 + 2Fc2)/3
5478 reflections	(Δ/σ)max = 0.031
280 parameters	Δρmax = 0.24 e Å−3
0 restraints	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
O2	0.70764 (6)	0.09270 (7)	0.44631 (14)	0.0483 (3)
O3	0.86302 (8)	−0.14409 (10)	0.4169 (2)	0.0700 (4)
O1	0.73699 (8)	−0.14734 (9)	0.68811 (17)	0.0632 (4)
O4	0.79918 (8)	−0.10360 (10)	0.18406 (17)	0.0667 (4)
N1	0.65661 (8)	0.03750 (9)	0.35751 (17)	0.0434 (3)
O5	0.91863 (8)	0.05907 (11)	0.3191 (2)	0.0835 (5)
C8	0.76235 (9)	−0.04489 (11)	0.4528 (2)	0.0456 (4)
C20	0.64690 (9)	0.06345 (11)	0.1815 (2)	0.0439 (4)
C7	0.68195 (9)	−0.05364 (10)	0.3918 (2)	0.0426 (4)
H7	0.6806	−0.0866	0.2829	0.051*
C25	0.66789 (12)	0.14637 (12)	0.1260 (2)	0.0574 (5)
H25	0.6940	0.1831	0.1998	0.069*
C6	0.63369 (10)	−0.09929 (10)	0.5208 (2)	0.0456 (4)
C12	0.77738 (9)	0.05377 (11)	0.4147 (2)	0.0463 (4)
H12	0.7899	0.0610	0.2924	0.056*
C5	0.55870 (10)	−0.09931 (11)	0.4991 (2)	0.0512 (4)
H5	0.5380	−0.0670	0.4092	0.061*
C1	0.66301 (11)	−0.14728 (11)	0.6568 (2)	0.0532 (4)
C13	0.83338 (11)	0.09872 (11)	0.5257 (2)	0.0549 (4)
C10	0.81416 (10)	−0.10354 (11)	0.3522 (2)	0.0503 (4)
C9	0.76871 (11)	−0.06416 (13)	0.6460 (2)	0.0565 (5)
H9A	0.8196	−0.0642	0.6801	0.068*
H9B	0.7444	−0.0183	0.7104	0.068*
C14	0.90540 (11)	0.10027 (12)	0.4729 (3)	0.0640 (5)
C21	0.60827 (10)	0.00969 (12)	0.0687 (2)	0.0529 (4)
H21	0.5934	−0.0457	0.1044	0.064*
C4	0.51420 (12)	−0.14634 (13)	0.6085 (3)	0.0635 (5)
H4	0.4640	−0.1452	0.5929	0.076*
C24	0.64973 (14)	0.17402 (15)	−0.0393 (3)	0.0731 (6)
H24	0.6633	0.2299	−0.0749	0.088*
C22	0.59180 (12)	0.03867 (15)	−0.0977 (2)	0.0650 (5)
H22	0.5666	0.0020	−0.1735	0.078*
C18	0.81593 (14)	0.13951 (14)	0.6799 (3)	0.0714 (6)
H18	0.7678	0.1398	0.7162	0.086*
C23	0.61227 (14)	0.12089 (16)	−0.1515 (3)	0.0734 (6)
H23	0.6008	0.1401	−0.2627	0.088*
C2	0.61876 (13)	−0.19588 (13)	0.7667 (3)	0.0679 (6)
H2	0.6391	−0.2285	0.8565	0.082*
C3	0.54475 (14)	−0.19499 (15)	0.7408 (3)	0.0732 (6)
H3	0.5149	−0.2275	0.8133	0.088*
C15	0.95828 (13)	0.14082 (15)	0.5751 (4)	0.0845 (8)
H15	1.0066	0.1413	0.5400	0.101*
C17	0.86869 (17)	0.17994 (18)	0.7813 (4)	0.0917 (8)
H17	0.8562	0.2067	0.8851	0.110*
C11	0.84555 (15)	−0.15710 (19)	0.0768 (3)	0.0894 (8)
H11A	0.8301	−0.1523	−0.0419	0.134*
H11B	0.8423	−0.2172	0.1131	0.134*
H11C	0.8950	−0.1374	0.0881	0.134*
C16	0.93901 (18)	0.18001 (17)	0.7273 (4)	0.0971 (9)
H16	0.9745	0.2071	0.7951	0.116*
C19	0.98762 (16)	0.0700 (2)	0.2409 (5)	0.1113 (11)
H19A	0.9888	0.0379	0.1340	0.167*
H19B	1.0249	0.0483	0.3175	0.167*
H19C	0.9958	0.1311	0.2183	0.167*

	U11	U22	U33	U12	U13	U23
O2	0.0549 (7)	0.0414 (6)	0.0488 (6)	0.0020 (5)	−0.0010 (5)	−0.0077 (5)
O3	0.0567 (8)	0.0680 (9)	0.0852 (10)	0.0145 (7)	−0.0006 (7)	0.0109 (7)
O1	0.0704 (9)	0.0569 (8)	0.0621 (8)	0.0013 (6)	−0.0071 (6)	0.0185 (6)
O4	0.0702 (9)	0.0720 (9)	0.0579 (8)	0.0221 (7)	0.0024 (6)	−0.0124 (6)
N1	0.0489 (8)	0.0390 (7)	0.0423 (7)	0.0010 (6)	−0.0015 (6)	0.0005 (5)
O5	0.0618 (10)	0.0805 (11)	0.1085 (13)	−0.0042 (8)	0.0218 (9)	−0.0086 (9)
C8	0.0499 (9)	0.0412 (8)	0.0457 (8)	0.0014 (7)	−0.0021 (7)	0.0010 (7)
C20	0.0470 (9)	0.0433 (8)	0.0416 (8)	0.0052 (7)	0.0068 (7)	0.0026 (6)
C7	0.0498 (9)	0.0373 (8)	0.0406 (7)	0.0020 (6)	0.0002 (6)	−0.0001 (6)
C25	0.0795 (13)	0.0439 (9)	0.0490 (9)	0.0004 (9)	0.0094 (9)	0.0005 (7)
C6	0.0564 (10)	0.0357 (8)	0.0448 (8)	−0.0012 (7)	0.0018 (7)	−0.0013 (6)
C12	0.0505 (10)	0.0412 (8)	0.0472 (8)	−0.0001 (7)	0.0017 (7)	−0.0032 (7)
C5	0.0580 (11)	0.0434 (9)	0.0522 (9)	−0.0029 (8)	0.0040 (8)	−0.0024 (7)
C1	0.0644 (12)	0.0420 (9)	0.0532 (9)	−0.0008 (8)	0.0001 (8)	0.0041 (7)
C13	0.0583 (11)	0.0423 (9)	0.0641 (11)	−0.0051 (8)	−0.0055 (9)	−0.0011 (8)
C10	0.0480 (10)	0.0397 (8)	0.0634 (10)	0.0003 (7)	0.0004 (8)	0.0033 (7)
C9	0.0599 (11)	0.0585 (11)	0.0510 (9)	−0.0046 (9)	−0.0081 (8)	0.0068 (8)
C14	0.0602 (12)	0.0460 (10)	0.0859 (14)	−0.0023 (9)	−0.0037 (10)	0.0049 (10)
C21	0.0557 (11)	0.0529 (10)	0.0502 (9)	−0.0014 (8)	−0.0035 (8)	0.0028 (8)
C4	0.0636 (12)	0.0572 (11)	0.0698 (12)	−0.0112 (9)	0.0121 (10)	−0.0003 (9)
C24	0.1051 (18)	0.0593 (12)	0.0550 (11)	0.0036 (12)	0.0132 (11)	0.0155 (9)
C22	0.0696 (13)	0.0760 (13)	0.0493 (10)	0.0074 (11)	−0.0063 (9)	−0.0037 (9)
C18	0.0812 (15)	0.0627 (12)	0.0703 (13)	−0.0092 (11)	−0.0067 (11)	−0.0155 (10)
C23	0.0920 (16)	0.0829 (15)	0.0454 (10)	0.0132 (13)	0.0023 (10)	0.0154 (10)
C2	0.0915 (16)	0.0515 (11)	0.0610 (11)	−0.0048 (10)	0.0037 (11)	0.0170 (9)
C3	0.0824 (16)	0.0615 (12)	0.0761 (14)	−0.0158 (11)	0.0176 (12)	0.0134 (11)
C15	0.0590 (13)	0.0600 (13)	0.134 (2)	−0.0097 (10)	−0.0191 (14)	0.0133 (14)
C17	0.106 (2)	0.0773 (16)	0.0917 (17)	−0.0128 (15)	−0.0253 (15)	−0.0245 (13)
C11	0.0917 (18)	0.0971 (18)	0.0797 (15)	0.0306 (15)	0.0149 (13)	−0.0223 (14)
C16	0.098 (2)	0.0653 (15)	0.127 (2)	−0.0177 (14)	−0.0437 (18)	−0.0097 (16)
C19	0.0838 (19)	0.0871 (19)	0.164 (3)	−0.0004 (15)	0.0523 (19)	0.0032 (19)

O2—N1	1.4306 (17)	C13—C14	1.389 (3)
O2—C12	1.436 (2)	C9—H9A	0.9700
O3—C10	1.196 (2)	C9—H9B	0.9700
O1—C1	1.379 (2)	C14—C15	1.391 (3)
O1—C9	1.435 (2)	C21—C22	1.390 (2)
O4—C10	1.325 (2)	C21—H21	0.9300
O4—C11	1.446 (3)	C4—C3	1.378 (3)
N1—C20	1.426 (2)	C4—H4	0.9300
N1—C7	1.489 (2)	C24—C23	1.368 (3)
O5—C14	1.368 (3)	C24—H24	0.9300
O5—C19	1.419 (3)	C22—C23	1.374 (3)
C8—C10	1.524 (2)	C22—H22	0.9300
C8—C9	1.524 (2)	C18—C17	1.386 (3)
C8—C7	1.553 (2)	C18—H18	0.9300
C8—C12	1.558 (2)	C23—H23	0.9300
C20—C21	1.387 (2)	C2—C3	1.373 (3)
C20—C25	1.391 (2)	C2—H2	0.9300
C7—C6	1.510 (2)	C3—H3	0.9300
C7—H7	0.9800	C15—C16	1.369 (4)
C25—C24	1.382 (3)	C15—H15	0.9300
C25—H25	0.9300	C17—C16	1.361 (4)
C6—C1	1.385 (2)	C17—H17	0.9300
C6—C5	1.387 (3)	C11—H11A	0.9600
C12—C13	1.500 (2)	C11—H11B	0.9600
C12—H12	0.9800	C11—H11C	0.9600
C5—C4	1.382 (3)	C16—H16	0.9300
C5—H5	0.9300	C19—H19A	0.9600
C1—C2	1.394 (3)	C19—H19B	0.9600
C13—C18	1.384 (3)	C19—H19C	0.9600
N1—O2—C12	104.93 (11)	C8—C9—H9B	109.3
C1—O1—C9	111.21 (13)	H9A—C9—H9B	108.0
C10—O4—C11	116.32 (16)	O5—C14—C15	124.6 (2)
C20—N1—O2	111.71 (12)	O5—C14—C13	115.12 (18)
C20—N1—C7	117.71 (12)	C15—C14—C13	120.3 (2)
O2—N1—C7	105.14 (11)	C20—C21—C22	119.92 (18)
C14—O5—C19	118.8 (2)	C20—C21—H21	120.0
C10—C8—C9	110.07 (14)	C22—C21—H21	120.0
C10—C8—C7	113.09 (13)	C3—C4—C5	119.5 (2)
C9—C8—C7	110.18 (14)	C3—C4—H4	120.2
C10—C8—C12	110.94 (14)	C5—C4—H4	120.2
C9—C8—C12	111.05 (14)	C23—C24—C25	121.4 (2)
C7—C8—C12	101.27 (12)	C23—C24—H24	119.3
C21—C20—C25	119.05 (15)	C25—C24—H24	119.3
C21—C20—N1	119.60 (15)	C23—C22—C21	120.78 (19)
C25—C20—N1	120.90 (15)	C23—C22—H22	119.6
N1—C7—C6	111.29 (13)	C21—C22—H22	119.6
N1—C7—C8	105.62 (12)	C13—C18—C17	121.3 (2)
C6—C7—C8	113.73 (13)	C13—C18—H18	119.3
N1—C7—H7	108.7	C17—C18—H18	119.3
C6—C7—H7	108.7	C24—C23—C22	119.11 (18)
C8—C7—H7	108.7	C24—C23—H23	120.4
C24—C25—C20	119.77 (18)	C22—C23—H23	120.4
C24—C25—H25	120.1	C3—C2—C1	119.25 (19)
C20—C25—H25	120.1	C3—C2—H2	120.4
C1—C6—C5	118.08 (16)	C1—C2—H2	120.4
C1—C6—C7	121.14 (16)	C2—C3—C4	120.65 (19)
C5—C6—C7	120.63 (15)	C2—C3—H3	119.7
O2—C12—C13	108.84 (14)	C4—C3—H3	119.7
O2—C12—C8	101.94 (13)	C16—C15—C14	119.8 (3)
C13—C12—C8	117.07 (14)	C16—C15—H15	120.1
O2—C12—H12	109.5	C14—C15—H15	120.1
C13—C12—H12	109.5	C16—C17—C18	119.3 (3)
C8—C12—H12	109.5	C16—C17—H17	120.4
C4—C5—C6	121.29 (18)	C18—C17—H17	120.4
C4—C5—H5	119.4	O4—C11—H11A	109.5
C6—C5—H5	119.4	O4—C11—H11B	109.5
O1—C1—C6	120.62 (16)	H11A—C11—H11B	109.5
O1—C1—C2	118.22 (16)	O4—C11—H11C	109.5
C6—C1—C2	121.16 (18)	H11A—C11—H11C	109.5
C18—C13—C14	118.28 (19)	H11B—C11—H11C	109.5
C18—C13—C12	122.30 (19)	C17—C16—C15	121.1 (2)
C14—C13—C12	119.42 (18)	C17—C16—H16	119.5
O3—C10—O4	123.87 (18)	C15—C16—H16	119.5
O3—C10—C8	124.12 (17)	O5—C19—H19A	109.5
O4—C10—C8	112.00 (14)	O5—C19—H19B	109.5
O1—C9—C8	111.39 (14)	H19A—C19—H19B	109.5
O1—C9—H9A	109.3	O5—C19—H19C	109.5
C8—C9—H9A	109.3	H19A—C19—H19C	109.5
O1—C9—H9B	109.3	H19B—C19—H19C	109.5
C12—O2—N1—C20	−87.53 (14)	C8—C12—C13—C18	−88.9 (2)
C12—O2—N1—C7	41.24 (15)	O2—C12—C13—C14	−153.74 (16)
O2—N1—C20—C21	170.08 (14)	C8—C12—C13—C14	91.4 (2)
C7—N1—C20—C21	48.3 (2)	C11—O4—C10—O3	0.4 (3)
O2—N1—C20—C25	−17.7 (2)	C11—O4—C10—C8	179.75 (18)
C7—N1—C20—C25	−139.49 (17)	C9—C8—C10—O3	−14.9 (2)
C20—N1—C7—C6	−129.01 (15)	C7—C8—C10—O3	−138.62 (17)
O2—N1—C7—C6	105.90 (14)	C12—C8—C10—O3	108.40 (19)
C20—N1—C7—C8	107.13 (15)	C9—C8—C10—O4	165.77 (15)
O2—N1—C7—C8	−17.97 (15)	C7—C8—C10—O4	42.1 (2)
C10—C8—C7—N1	−128.15 (14)	C12—C8—C10—O4	−70.92 (18)
C9—C8—C7—N1	108.20 (15)	C1—O1—C9—C8	−64.7 (2)
C12—C8—C7—N1	−9.40 (15)	C10—C8—C9—O1	−71.94 (19)
C10—C8—C7—C6	109.53 (16)	C7—C8—C9—O1	53.44 (19)
C9—C8—C7—C6	−14.11 (19)	C12—C8—C9—O1	164.82 (15)
C12—C8—C7—C6	−131.72 (14)	C19—O5—C14—C15	−11.3 (3)
C21—C20—C25—C24	0.3 (3)	C19—O5—C14—C13	169.5 (2)
N1—C20—C25—C24	−171.90 (18)	C18—C13—C14—O5	−179.71 (18)
N1—C7—C6—C1	−134.52 (15)	C12—C13—C14—O5	0.0 (3)
C8—C7—C6—C1	−15.4 (2)	C18—C13—C14—C15	1.0 (3)
N1—C7—C6—C5	50.02 (19)	C12—C13—C14—C15	−179.30 (18)
C8—C7—C6—C5	169.15 (14)	C25—C20—C21—C22	0.7 (3)
N1—O2—C12—C13	−171.11 (12)	N1—C20—C21—C22	173.05 (17)
N1—O2—C12—C8	−46.80 (14)	C6—C5—C4—C3	−0.7 (3)
C10—C8—C12—O2	153.58 (13)	C20—C25—C24—C23	−1.0 (3)
C9—C8—C12—O2	−83.68 (16)	C20—C21—C22—C23	−1.1 (3)
C7—C8—C12—O2	33.30 (14)	C14—C13—C18—C17	−0.9 (3)
C10—C8—C12—C13	−87.82 (18)	C12—C13—C18—C17	179.4 (2)
C9—C8—C12—C13	34.9 (2)	C25—C24—C23—C22	0.6 (4)
C7—C8—C12—C13	151.90 (15)	C21—C22—C23—C24	0.5 (3)
C1—C6—C5—C4	−0.6 (3)	O1—C1—C2—C3	178.34 (19)
C7—C6—C5—C4	174.99 (16)	C6—C1—C2—C3	−1.0 (3)
C9—O1—C1—C6	33.7 (2)	C1—C2—C3—C4	−0.4 (3)
C9—O1—C1—C2	−145.58 (18)	C5—C4—C3—C2	1.2 (3)
C5—C6—C1—O1	−177.86 (15)	O5—C14—C15—C16	−179.8 (2)
C7—C6—C1—O1	6.6 (2)	C13—C14—C15—C16	−0.6 (3)
C5—C6—C1—C2	1.4 (3)	C13—C18—C17—C16	0.5 (4)
C7—C6—C1—C2	−174.15 (16)	C18—C17—C16—C15	−0.1 (4)
O2—C12—C13—C18	26.0 (2)	C14—C15—C16—C17	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O4	0.98	2.33	2.803 (2)	109
C15—H15···O3i	0.93	2.42	3.285 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O4	0.98	2.33	2.803 (2)	109
C15—H15⋯O3i	0.93	2.42	3.285 (3)	155

Symmetry code: (i) .