8-Bromo-3-(4-ethyl-phen-yl)-1-phenyl-3,3a,4,9b-tetra-hydro-1H-chromeno[4,3-c]isoxazole-3a-carbo-nitrile.

In the title compound, C25H21BrN2O2, the fused isoxazolidine ring adopts an envelope conformation with the N atom at the flap and the mean plane of the ring makes dihedral angles of 54.37 (12) and 87.32 (13)°, respectively, with the adjacent phenyl and benzene rings. The tetra-hydro-pyran ring has a half-chair conformation. In the crystal, mol-ecules are linked into a double-column structure along the b-axis direction through weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological activity of cyano­acrylates, see: Zhang et al. (2009 ▶); Obniska et al. (2005 ▶). For related structures, see: Ye et al. (2009 ▶); Suresh et al. (2012 ▶); Kanchanadevi et al. (2013 ▶).

Experimental

Crystal data

C25H21BrN2O2

M = 461.35

Triclinic,

a = 9.8813 (3) Å

b = 9.9921 (3) Å

c = 11.1587 (3) Å

α = 94.125 (2)°

β = 92.196 (2)°

γ = 101.500 (2)°

V = 1075.27 (5) Å3

Z = 2

Mo Kα radiation

μ = 1.94 mm−1

T = 295 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.620, T max = 0.748

27480 measured reflections

6895 independent reflections

4405 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.02

6895 reflections

274 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.81 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813023982/is5299sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023982/is5299Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023982/is5299Isup3.cml

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

C25H21BrN2O2	Z = 2
Mr = 461.35	F(000) = 472
Triclinic, P1	Dx = 1.425 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8813 (3) Å	Cell parameters from 4405 reflections
b = 9.9921 (3) Å	θ = 2.1–31.1°
c = 11.1587 (3) Å	µ = 1.94 mm−1
α = 94.125 (2)°	T = 295 K
β = 92.196 (2)°	Block, colourless
γ = 101.500 (2)°	0.25 × 0.20 × 0.15 mm
V = 1075.27 (5) Å3

Bruker APEXII CCD diffractometer	6895 independent reflections
Radiation source: fine-focus sealed tube	4405 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 0 pixels mm-1	θmax = 31.1°, θmin = 2.1°
ω and φ scans	h = −13→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.620, Tmax = 0.748	l = −16→15
27480 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.3505P] where P = (Fo2 + 2Fc2)/3
6895 reflections	(Δ/σ)max = 0.001
274 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.81 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.04591 (3)	0.59905 (3)	0.29647 (2)	0.06392 (11)
O1	0.42095 (16)	0.48260 (14)	0.69339 (13)	0.0480 (4)
O2	0.32836 (18)	0.04730 (14)	0.52461 (12)	0.0479 (4)
N1	0.33533 (18)	0.17431 (16)	0.46483 (14)	0.0387 (4)
C6	0.3363 (2)	0.23582 (19)	0.66704 (16)	0.0366 (4)
C8	0.2571 (2)	0.39431 (18)	0.52539 (16)	0.0350 (4)
N2	0.1838 (2)	0.2514 (2)	0.85005 (17)	0.0566 (5)
C7	0.2565 (2)	0.24777 (18)	0.54874 (15)	0.0337 (4)
H7	0.1611	0.1965	0.5498	0.040*
C16	0.3846 (2)	0.0964 (2)	0.64292 (17)	0.0417 (4)
H16	0.4857	0.1146	0.6425	0.050*
C10	0.2740 (2)	0.13817 (19)	0.34525 (16)	0.0366 (4)
C12	0.2584 (2)	0.2032 (2)	0.14426 (18)	0.0490 (5)
H12	0.2816	0.2674	0.0883	0.059*
C17	0.3385 (2)	−0.0105 (2)	0.72803 (18)	0.0422 (4)
C9	0.1687 (2)	0.4248 (2)	0.43612 (17)	0.0390 (4)
H9	0.1143	0.3544	0.3861	0.047*
C5	0.4613 (2)	0.3539 (2)	0.68345 (19)	0.0449 (5)
H5A	0.5157	0.3445	0.7554	0.054*
H5B	0.5188	0.3499	0.6153	0.054*
C22	0.4339 (3)	−0.0410 (2)	0.81004 (19)	0.0512 (5)
H22	0.5263	0.0027	0.8100	0.061*
C25	0.2495 (2)	0.2419 (2)	0.77047 (17)	0.0408 (4)
C4	0.3342 (2)	0.50191 (19)	0.60093 (17)	0.0391 (4)
C15	0.1848 (2)	0.0155 (2)	0.31184 (19)	0.0480 (5)
H15	0.1581	−0.0473	0.3684	0.058*
C13	0.1712 (3)	0.0798 (3)	0.1099 (2)	0.0544 (6)
H13	0.1368	0.0599	0.0305	0.065*
C11	0.3113 (2)	0.2318 (2)	0.26118 (17)	0.0419 (4)
H11	0.3723	0.3142	0.2836	0.050*
C14	0.1354 (3)	−0.0133 (2)	0.1927 (2)	0.0570 (6)
H14	0.0772	−0.0970	0.1691	0.068*
C3	0.3218 (2)	0.6360 (2)	0.5880 (2)	0.0484 (5)
H3	0.3717	0.7065	0.6406	0.058*
C21	0.3925 (3)	−0.1363 (3)	0.8921 (2)	0.0663 (7)
H21	0.4575	−0.1547	0.9477	0.080*
C2	0.2369 (3)	0.6649 (2)	0.4985 (2)	0.0509 (5)
H2	0.2297	0.7550	0.4893	0.061*
C18	0.2022 (3)	−0.0779 (2)	0.7290 (2)	0.0526 (5)
H18	0.1369	−0.0588	0.6741	0.063*
C1	0.1616 (2)	0.5591 (2)	0.42159 (18)	0.0435 (5)
C19	0.1623 (3)	−0.1735 (3)	0.8109 (3)	0.0635 (7)
H19	0.0701	−0.2179	0.8105	0.076*
C20	0.2571 (4)	−0.2044 (3)	0.8934 (3)	0.0696 (8)
C23	0.2127 (6)	−0.3092 (5)	0.9833 (4)	0.1272 (18)
H23A	0.2132	−0.2599	1.0615	0.153*
H23B	0.1177	−0.3540	0.9615	0.153*
C24	0.2878 (8)	−0.4092 (5)	0.9959 (6)	0.176 (3)
H24A	0.2747	−0.4704	0.9241	0.265*
H24B	0.2573	−0.4596	1.0633	0.265*
H24C	0.3841	−0.3678	1.0091	0.265*

	U11	U22	U33	U12	U13	U23
Br1	0.0752 (2)	0.07064 (18)	0.05709 (16)	0.03362 (14)	0.00511 (12)	0.02685 (12)
O1	0.0583 (9)	0.0377 (7)	0.0422 (8)	−0.0007 (6)	−0.0080 (7)	−0.0010 (6)
O2	0.0789 (11)	0.0361 (7)	0.0330 (7)	0.0220 (7)	−0.0028 (7)	0.0050 (5)
N1	0.0537 (10)	0.0346 (8)	0.0295 (7)	0.0124 (7)	0.0001 (7)	0.0047 (6)
C6	0.0455 (11)	0.0356 (9)	0.0288 (8)	0.0079 (8)	−0.0005 (7)	0.0055 (7)
C8	0.0429 (10)	0.0304 (8)	0.0320 (8)	0.0066 (7)	0.0053 (7)	0.0049 (7)
N2	0.0735 (14)	0.0594 (12)	0.0382 (9)	0.0142 (10)	0.0083 (9)	0.0069 (8)
C7	0.0412 (10)	0.0300 (8)	0.0291 (8)	0.0052 (7)	0.0001 (7)	0.0039 (6)
C16	0.0513 (12)	0.0412 (10)	0.0350 (9)	0.0146 (9)	−0.0007 (8)	0.0062 (8)
C10	0.0436 (10)	0.0357 (9)	0.0308 (8)	0.0095 (8)	0.0011 (8)	0.0014 (7)
C12	0.0593 (13)	0.0541 (12)	0.0352 (10)	0.0124 (10)	0.0019 (9)	0.0112 (9)
C17	0.0581 (13)	0.0356 (9)	0.0366 (9)	0.0177 (9)	0.0012 (9)	0.0050 (7)
C9	0.0456 (11)	0.0371 (9)	0.0358 (9)	0.0106 (8)	0.0040 (8)	0.0054 (7)
C5	0.0453 (11)	0.0463 (11)	0.0409 (10)	0.0058 (9)	−0.0069 (9)	0.0043 (8)
C22	0.0624 (14)	0.0549 (12)	0.0409 (11)	0.0214 (11)	−0.0019 (10)	0.0099 (9)
C25	0.0541 (12)	0.0369 (9)	0.0306 (9)	0.0073 (9)	−0.0022 (8)	0.0062 (7)
C4	0.0460 (11)	0.0349 (9)	0.0349 (9)	0.0039 (8)	0.0063 (8)	0.0034 (7)
C15	0.0581 (13)	0.0408 (11)	0.0420 (11)	0.0018 (9)	0.0013 (10)	0.0070 (8)
C13	0.0632 (15)	0.0609 (14)	0.0367 (10)	0.0113 (12)	−0.0076 (10)	−0.0032 (10)
C11	0.0499 (12)	0.0375 (10)	0.0362 (9)	0.0035 (8)	0.0011 (8)	0.0049 (8)
C14	0.0661 (15)	0.0468 (12)	0.0502 (12)	−0.0016 (11)	−0.0082 (11)	−0.0059 (10)
C3	0.0578 (13)	0.0316 (9)	0.0534 (12)	0.0043 (9)	0.0090 (10)	−0.0021 (8)
C21	0.090 (2)	0.0736 (17)	0.0475 (13)	0.0376 (15)	0.0040 (13)	0.0240 (12)
C2	0.0689 (15)	0.0333 (10)	0.0554 (12)	0.0172 (10)	0.0163 (11)	0.0099 (9)
C18	0.0597 (14)	0.0463 (12)	0.0552 (13)	0.0176 (10)	0.0010 (11)	0.0091 (10)
C1	0.0510 (12)	0.0446 (11)	0.0412 (10)	0.0192 (9)	0.0118 (9)	0.0144 (8)
C19	0.0729 (17)	0.0464 (12)	0.0751 (17)	0.0147 (12)	0.0211 (14)	0.0150 (12)
C20	0.101 (2)	0.0574 (14)	0.0624 (15)	0.0338 (15)	0.0275 (15)	0.0264 (12)
C23	0.182 (5)	0.104 (3)	0.122 (3)	0.057 (3)	0.067 (3)	0.080 (3)
C24	0.283 (8)	0.101 (3)	0.174 (5)	0.071 (4)	0.070 (5)	0.086 (4)

Br1—C1	1.886 (2)	C5—H5B	0.9700
O1—C4	1.365 (3)	C22—C21	1.382 (3)
O1—C5	1.418 (3)	C22—H22	0.9300
O2—C16	1.426 (2)	C4—C3	1.386 (3)
O2—N1	1.467 (2)	C15—C14	1.388 (3)
N1—C10	1.435 (2)	C15—H15	0.9300
N1—C7	1.485 (2)	C13—C14	1.365 (4)
C6—C25	1.469 (3)	C13—H13	0.9300
C6—C5	1.524 (3)	C11—H11	0.9300
C6—C7	1.536 (2)	C14—H14	0.9300
C6—C16	1.569 (3)	C3—C2	1.363 (3)
C8—C9	1.389 (3)	C3—H3	0.9300
C8—C4	1.393 (3)	C21—C20	1.376 (4)
C8—C7	1.505 (2)	C21—H21	0.9300
N2—C25	1.130 (3)	C2—C1	1.384 (3)
C7—H7	0.9800	C2—H2	0.9300
C16—C17	1.495 (3)	C18—C19	1.381 (3)
C16—H16	0.9800	C18—H18	0.9300
C10—C15	1.377 (3)	C19—C20	1.382 (4)
C10—C11	1.381 (3)	C19—H19	0.9300
C12—C13	1.375 (3)	C20—C23	1.516 (4)
C12—C11	1.376 (3)	C23—C24	1.371 (6)
C12—H12	0.9300	C23—H23A	0.9700
C17—C18	1.381 (3)	C23—H23B	0.9700
C17—C22	1.382 (3)	C24—H24A	0.9600
C9—C1	1.379 (3)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C5—H5A	0.9700
C4—O1—C5	114.15 (15)	O1—C4—C3	116.29 (18)
C16—O2—N1	102.54 (13)	O1—C4—C8	122.97 (17)
C10—N1—O2	107.73 (14)	C3—C4—C8	120.7 (2)
C10—N1—C7	115.95 (15)	C10—C15—C14	119.2 (2)
O2—N1—C7	99.71 (13)	C10—C15—H15	120.4
C25—C6—C5	109.23 (16)	C14—C15—H15	120.4
C25—C6—C7	111.41 (16)	C14—C13—C12	119.8 (2)
C5—C6—C7	108.42 (15)	C14—C13—H13	120.1
C25—C6—C16	114.63 (16)	C12—C13—H13	120.1
C5—C6—C16	110.13 (17)	C12—C11—C10	120.00 (19)
C7—C6—C16	102.74 (14)	C12—C11—H11	120.0
C9—C8—C4	118.41 (17)	C10—C11—H11	120.0
C9—C8—C7	120.38 (17)	C13—C14—C15	120.8 (2)
C4—C8—C7	120.82 (17)	C13—C14—H14	119.6
N1—C7—C8	115.44 (15)	C15—C14—H14	119.6
N1—C7—C6	98.84 (14)	C2—C3—C4	120.4 (2)
C8—C7—C6	112.34 (15)	C2—C3—H3	119.8
N1—C7—H7	109.9	C4—C3—H3	119.8
C8—C7—H7	109.9	C20—C21—C22	121.5 (2)
C6—C7—H7	109.9	C20—C21—H21	119.3
O2—C16—C17	109.47 (17)	C22—C21—H21	119.3
O2—C16—C6	104.02 (15)	C3—C2—C1	119.47 (19)
C17—C16—C6	116.39 (16)	C3—C2—H2	120.3
O2—C16—H16	108.9	C1—C2—H2	120.3
C17—C16—H16	108.9	C17—C18—C19	120.5 (2)
C6—C16—H16	108.9	C17—C18—H18	119.7
C15—C10—C11	120.04 (18)	C19—C18—H18	119.7
C15—C10—N1	123.18 (17)	C9—C1—C2	120.9 (2)
C11—C10—N1	116.75 (17)	C9—C1—Br1	119.56 (16)
C13—C12—C11	120.2 (2)	C2—C1—Br1	119.56 (15)
C13—C12—H12	119.9	C18—C19—C20	121.1 (3)
C11—C12—H12	119.9	C18—C19—H19	119.5
C18—C17—C22	118.8 (2)	C20—C19—H19	119.5
C18—C17—C16	121.91 (19)	C21—C20—C19	118.0 (2)
C22—C17—C16	119.3 (2)	C21—C20—C23	121.1 (3)
C1—C9—C8	120.11 (19)	C19—C20—C23	120.9 (3)
C1—C9—H9	119.9	C24—C23—C20	118.3 (4)
C8—C9—H9	119.9	C24—C23—H23A	107.7
O1—C5—C6	111.55 (17)	C20—C23—H23A	107.7
O1—C5—H5A	109.3	C24—C23—H23B	107.7
C6—C5—H5A	109.3	C20—C23—H23B	107.7
O1—C5—H5B	109.3	H23A—C23—H23B	107.1
C6—C5—H5B	109.3	C23—C24—H24A	109.5
H5A—C5—H5B	108.0	C23—C24—H24B	109.5
C17—C22—C21	120.2 (2)	H24A—C24—H24B	109.5
C17—C22—H22	119.9	C23—C24—H24C	109.5
C21—C22—H22	119.9	H24A—C24—H24C	109.5
N2—C25—C6	177.6 (2)	H24B—C24—H24C	109.5
C16—O2—N1—C10	−176.95 (16)	C7—C6—C5—O1	62.4 (2)
C16—O2—N1—C7	−55.56 (17)	C16—C6—C5—O1	174.11 (15)
C10—N1—C7—C8	−72.5 (2)	C18—C17—C22—C21	−0.7 (3)
O2—N1—C7—C8	172.22 (15)	C16—C17—C22—C21	177.9 (2)
C10—N1—C7—C6	167.50 (15)	C5—O1—C4—C3	−162.91 (18)
O2—N1—C7—C6	52.22 (15)	C5—O1—C4—C8	19.5 (3)
C9—C8—C7—N1	80.4 (2)	C9—C8—C4—O1	178.12 (18)
C4—C8—C7—N1	−106.9 (2)	C7—C8—C4—O1	5.2 (3)
C9—C8—C7—C6	−167.34 (17)	C9—C8—C4—C3	0.7 (3)
C4—C8—C7—C6	5.4 (3)	C7—C8—C4—C3	−172.24 (18)
C25—C6—C7—N1	−154.08 (15)	C11—C10—C15—C14	1.0 (3)
C5—C6—C7—N1	85.69 (17)	N1—C10—C15—C14	−177.1 (2)
C16—C6—C7—N1	−30.87 (17)	C11—C12—C13—C14	1.2 (4)
C25—C6—C7—C8	83.6 (2)	C13—C12—C11—C10	−1.8 (3)
C5—C6—C7—C8	−36.6 (2)	C15—C10—C11—C12	0.7 (3)
C16—C6—C7—C8	−153.14 (16)	N1—C10—C11—C12	178.96 (19)
N1—O2—C16—C17	158.99 (16)	C12—C13—C14—C15	0.6 (4)
N1—O2—C16—C6	33.95 (19)	C10—C15—C14—C13	−1.7 (4)
C25—C6—C16—O2	119.69 (18)	O1—C4—C3—C2	−179.65 (19)
C5—C6—C16—O2	−116.68 (17)	C8—C4—C3—C2	−2.0 (3)
C7—C6—C16—O2	−1.34 (19)	C17—C22—C21—C20	1.0 (4)
C25—C6—C16—C17	−0.8 (3)	C4—C3—C2—C1	0.9 (3)
C5—C6—C16—C17	122.83 (19)	C22—C17—C18—C19	0.3 (3)
C7—C6—C16—C17	−121.83 (18)	C16—C17—C18—C19	−178.3 (2)
O2—N1—C10—C15	20.2 (3)	C8—C9—C1—C2	−3.0 (3)
C7—N1—C10—C15	−90.5 (2)	C8—C9—C1—Br1	177.82 (14)
O2—N1—C10—C11	−158.00 (17)	C3—C2—C1—C9	1.6 (3)
C7—N1—C10—C11	91.4 (2)	C3—C2—C1—Br1	−179.19 (17)
O2—C16—C17—C18	−47.1 (3)	C17—C18—C19—C20	−0.1 (4)
C6—C16—C17—C18	70.4 (3)	C22—C21—C20—C19	−0.9 (4)
O2—C16—C17—C22	134.4 (2)	C22—C21—C20—C23	179.7 (3)
C6—C16—C17—C22	−108.1 (2)	C18—C19—C20—C21	0.4 (4)
C4—C8—C9—C1	1.8 (3)	C18—C19—C20—C23	179.8 (3)
C7—C8—C9—C1	174.74 (17)	C21—C20—C23—C24	−49.4 (7)
C4—O1—C5—C6	−54.0 (2)	C19—C20—C23—C24	131.2 (5)
C25—C6—C5—O1	−59.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.57	3.475 (2)	165
C3—H3···Cg5ii	0.93	2.78	3.491 (3)	134
C5—H5B···Cg3i	0.97	2.86	3.730 (4)	149
C22—H22···Cg4iii	0.93	2.95	3.628 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg5 are the centroids of the C1–C4/C8/C9, C10–C15 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.57	3.475 (2)	165
C3—H3⋯Cg5ii	0.93	2.78	3.491 (3)	134
C5—H5B⋯Cg3i	0.97	2.86	3.730 (4)	149
C22—H22⋯Cg4iii	0.93	2.95	3.628 (3)	131

Symmetry codes: (i) ; (ii) ; (iii) .