8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo-nitrile.

In the title compound, C(17)H(11)BrN(2)O(2), the five-membered isoxazole ring has an envelope conformation with the C atom bearing the phenyl ring as the flap. The pyran ring has a half-chair conformation. In the chromeno ring system, the dihedral angle between the mean plane of the pyran ring and the benzene ring is 4.68 (2)°. The dihedral angle between the mean planes of the chromeno ring system and the isoxazole ring is 13.79 (15)°. The latter forms a dihedral angle of 34.10 (17)° with the phenyl ring. In the crystal, mol-ecules are linked by C-H⋯N hydrogen bonds, forming an undulating two-dimensional network parallel to the ab plane.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007 ▶, 2008 ▶); Cai et al. (2006 ▶); Caine (1993 ▶); Gabor (1988 ▶); Brooks (1998 ▶); Valenti et al. (1993 ▶); Hyana & Saimoto (1987 ▶); Tang et al. (2007 ▶). For related structures, see: Gangadharan et al. (2011 ▶); Swaminathan et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H11BrN2O2

M = 355.19

Monoclinic,

a = 15.1034 (8) Å

b = 6.0676 (3) Å

c = 16.0865 (10) Å

β = 99.953 (2)°

V = 1452.00 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.84 mm−1

T = 298 K

0.35 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.437, T max = 0.601

9947 measured reflections

3175 independent reflections

2214 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.102

S = 1.09

3175 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.96 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 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813002511/su2547sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002511/su2547Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002511/su2547Isup3.cml

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

C17H11BrN2O2	F(000) = 712
Mr = 355.19	Dx = 1.625 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3175 reflections
a = 15.1034 (8) Å	θ = 2.6–28.6°
b = 6.0676 (3) Å	µ = 2.84 mm−1
c = 16.0865 (10) Å	T = 298 K
β = 99.953 (2)°	Block, colourless
V = 1452.00 (14) Å3	0.35 × 0.28 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3175 independent reflections
Radiation source: fine-focus sealed tube	2214 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 28.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −20→17
Tmin = 0.437, Tmax = 0.601	k = −7→6
9947 measured reflections	l = −21→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0261P)2 + 2.1957P] where P = (Fo2 + 2Fc2)/3
3175 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.96 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
Br1	0.36162 (2)	0.32449 (7)	0.91825 (3)	0.05691 (17)
C1	0.5050 (3)	−0.1845 (7)	0.8336 (2)	0.0511 (10)
H1	0.4920	−0.3179	0.8057	0.061*
C2	0.4363 (2)	−0.0557 (7)	0.8528 (2)	0.0497 (10)
H2	0.3770	−0.1023	0.8383	0.060*
C3	0.4558 (2)	0.1418 (6)	0.8935 (2)	0.0409 (8)
C4	0.5432 (2)	0.2124 (6)	0.9171 (2)	0.0388 (8)
H4	0.5555	0.3452	0.9457	0.047*
C5	0.6132 (2)	0.0817 (6)	0.8976 (2)	0.0347 (7)
C6	0.7069 (2)	0.1465 (5)	0.9180 (2)	0.0327 (7)
C7	0.8603 (2)	0.0893 (6)	0.9367 (2)	0.0350 (8)
H7	0.8709	−0.0167	0.9834	0.042*
C8	0.7744 (2)	0.0220 (5)	0.87679 (19)	0.0328 (7)
C9	0.7483 (2)	−0.2215 (6)	0.8748 (2)	0.0442 (9)
H9A	0.7887	−0.3049	0.8460	0.053*
H9B	0.7545	−0.2768	0.9321	0.053*
C10	0.5935 (2)	−0.1162 (6)	0.8556 (2)	0.0397 (8)
C11	0.9454 (2)	0.1107 (6)	0.90087 (19)	0.0335 (8)
C12	0.9955 (2)	0.3024 (6)	0.9084 (2)	0.0463 (9)
H12	0.9750	0.4258	0.9336	0.056*
C13	1.0765 (3)	0.3117 (7)	0.8784 (2)	0.0540 (10)
H13	1.1104	0.4404	0.8846	0.065*
C14	1.1064 (2)	0.1313 (7)	0.8398 (2)	0.0527 (10)
H14	1.1606	0.1374	0.8199	0.063*
C15	1.0561 (2)	−0.0576 (7)	0.8308 (2)	0.0522 (10)
H15	1.0756	−0.1793	0.8038	0.063*
C16	0.9764 (2)	−0.0679 (6)	0.8617 (2)	0.0456 (9)
H16	0.9431	−0.1976	0.8560	0.055*
C17	0.7720 (2)	0.1102 (6)	0.7912 (2)	0.0380 (8)
N1	0.74127 (18)	0.2977 (5)	0.96850 (19)	0.0449 (7)
N2	0.7691 (2)	0.1831 (7)	0.7260 (2)	0.0633 (10)
O1	0.65812 (17)	−0.2523 (4)	0.83272 (17)	0.0518 (7)
O2	0.83596 (15)	0.2996 (4)	0.96973 (16)	0.0481 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.0352 (2)	0.0664 (3)	0.0693 (3)	0.00649 (18)	0.00961 (17)	0.0061 (2)
C1	0.052 (2)	0.045 (2)	0.056 (2)	−0.0149 (19)	0.0085 (18)	−0.008 (2)
C2	0.0376 (19)	0.057 (3)	0.053 (2)	−0.0119 (18)	0.0041 (17)	0.001 (2)
C3	0.0349 (17)	0.047 (2)	0.0410 (18)	0.0027 (16)	0.0061 (14)	0.0104 (17)
C4	0.0389 (17)	0.038 (2)	0.0381 (17)	0.0003 (15)	0.0040 (14)	0.0013 (16)
C5	0.0369 (17)	0.032 (2)	0.0340 (17)	−0.0008 (14)	0.0043 (14)	0.0040 (15)
C6	0.0357 (16)	0.027 (2)	0.0335 (16)	0.0036 (14)	0.0016 (13)	0.0014 (15)
C7	0.0383 (17)	0.032 (2)	0.0326 (17)	0.0088 (14)	0.0006 (14)	−0.0005 (15)
C8	0.0345 (16)	0.030 (2)	0.0336 (16)	0.0013 (14)	0.0045 (13)	−0.0002 (14)
C9	0.0441 (19)	0.030 (2)	0.060 (2)	0.0007 (16)	0.0144 (17)	−0.0027 (18)
C10	0.0440 (19)	0.035 (2)	0.0419 (19)	−0.0032 (16)	0.0114 (15)	−0.0004 (16)
C11	0.0320 (16)	0.036 (2)	0.0285 (15)	0.0068 (14)	−0.0057 (13)	0.0014 (14)
C12	0.053 (2)	0.039 (2)	0.046 (2)	0.0008 (18)	0.0048 (17)	−0.0044 (18)
C13	0.052 (2)	0.055 (3)	0.053 (2)	−0.012 (2)	0.0028 (18)	0.006 (2)
C14	0.0397 (19)	0.075 (3)	0.044 (2)	0.000 (2)	0.0071 (16)	0.008 (2)
C15	0.046 (2)	0.058 (3)	0.054 (2)	0.010 (2)	0.0119 (18)	−0.010 (2)
C16	0.0390 (18)	0.041 (2)	0.055 (2)	0.0029 (16)	0.0043 (16)	−0.0070 (19)
C17	0.0292 (16)	0.046 (2)	0.0365 (19)	−0.0046 (15)	−0.0017 (14)	0.0008 (17)
N1	0.0341 (15)	0.045 (2)	0.0549 (18)	0.0062 (14)	0.0051 (13)	−0.0105 (16)
N2	0.0420 (17)	0.095 (3)	0.049 (2)	−0.0085 (18)	−0.0012 (15)	0.022 (2)
O1	0.0490 (15)	0.0387 (15)	0.0700 (18)	−0.0083 (12)	0.0170 (13)	−0.0172 (14)
O2	0.0321 (12)	0.0495 (16)	0.0604 (16)	0.0037 (11)	0.0012 (11)	−0.0236 (13)

Br1—C3	1.899 (3)	C8—C9	1.528 (5)
C1—C2	1.376 (5)	C9—O1	1.425 (4)
C1—C10	1.385 (5)	C9—H9A	0.9700
C1—H1	0.9300	C9—H9B	0.9700
C2—C3	1.373 (5)	C10—O1	1.377 (4)
C2—H2	0.9300	C11—C16	1.375 (5)
C3—C4	1.377 (5)	C11—C12	1.382 (5)
C4—C5	1.400 (5)	C12—C13	1.390 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C10	1.384 (5)	C13—C14	1.373 (6)
C5—C6	1.451 (4)	C13—H13	0.9300
C6—N1	1.275 (4)	C14—C15	1.369 (6)
C6—C8	1.512 (4)	C14—H14	0.9300
C7—O2	1.454 (4)	C15—C16	1.381 (5)
C7—C11	1.502 (4)	C15—H15	0.9300
C7—C8	1.532 (4)	C16—H16	0.9300
C7—H7	0.9800	C17—N2	1.132 (4)
C8—C17	1.472 (5)	N1—O2	1.427 (3)
C2—C1—C10	120.3 (4)	O1—C9—H9A	109.4
C2—C1—H1	119.9	C8—C9—H9A	109.4
C10—C1—H1	119.9	O1—C9—H9B	109.4
C3—C2—C1	119.6 (3)	C8—C9—H9B	109.4
C3—C2—H2	120.2	H9A—C9—H9B	108.0
C1—C2—H2	120.2	O1—C10—C5	123.2 (3)
C2—C3—C4	121.3 (3)	O1—C10—C1	116.7 (3)
C2—C3—Br1	120.2 (3)	C5—C10—C1	120.0 (3)
C4—C3—Br1	118.5 (3)	C16—C11—C12	118.6 (3)
C3—C4—C5	119.1 (3)	C16—C11—C7	119.3 (3)
C3—C4—H4	120.4	C12—C11—C7	122.1 (3)
C5—C4—H4	120.4	C11—C12—C13	120.4 (4)
C10—C5—C4	119.6 (3)	C11—C12—H12	119.8
C10—C5—C6	117.7 (3)	C13—C12—H12	119.8
C4—C5—C6	122.7 (3)	C14—C13—C12	120.1 (4)
N1—C6—C5	127.9 (3)	C14—C13—H13	119.9
N1—C6—C8	114.0 (3)	C12—C13—H13	119.9
C5—C6—C8	118.1 (3)	C15—C14—C13	119.7 (3)
O2—C7—C11	110.6 (3)	C15—C14—H14	120.2
O2—C7—C8	102.9 (2)	C13—C14—H14	120.2
C11—C7—C8	118.0 (3)	C14—C15—C16	120.1 (4)
O2—C7—H7	108.3	C14—C15—H15	119.9
C11—C7—H7	108.3	C16—C15—H15	119.9
C8—C7—H7	108.3	C11—C16—C15	121.1 (4)
C17—C8—C6	108.6 (3)	C11—C16—H16	119.5
C17—C8—C9	111.6 (3)	C15—C16—H16	119.5
C6—C8—C9	107.5 (3)	N2—C17—C8	178.2 (4)
C17—C8—C7	111.9 (3)	C6—N1—O2	108.2 (3)
C6—C8—C7	98.8 (2)	C10—O1—C9	117.3 (3)
C9—C8—C7	117.3 (3)	N1—O2—C7	107.7 (2)
O1—C9—C8	111.0 (3)
C10—C1—C2—C3	0.4 (6)	C4—C5—C10—O1	178.8 (3)
C1—C2—C3—C4	−1.3 (5)	C6—C5—C10—O1	−0.1 (5)
C1—C2—C3—Br1	178.6 (3)	C4—C5—C10—C1	−0.3 (5)
C2—C3—C4—C5	1.3 (5)	C6—C5—C10—C1	−179.2 (3)
Br1—C3—C4—C5	−178.6 (2)	C2—C1—C10—O1	−178.8 (3)
C3—C4—C5—C10	−0.5 (5)	C2—C1—C10—C5	0.4 (6)
C3—C4—C5—C6	178.3 (3)	O2—C7—C11—C16	−175.9 (3)
C10—C5—C6—N1	−166.3 (3)	C8—C7—C11—C16	−58.0 (4)
C4—C5—C6—N1	14.9 (5)	O2—C7—C11—C12	6.3 (4)
C10—C5—C6—C8	12.9 (4)	C8—C7—C11—C12	124.3 (3)
C4—C5—C6—C8	−166.0 (3)	C16—C11—C12—C13	−1.3 (5)
N1—C6—C8—C17	−99.7 (3)	C7—C11—C12—C13	176.4 (3)
C5—C6—C8—C17	81.0 (4)	C11—C12—C13—C14	1.1 (6)
N1—C6—C8—C9	139.5 (3)	C12—C13—C14—C15	0.1 (6)
C5—C6—C8—C9	−39.8 (4)	C13—C14—C15—C16	−1.1 (6)
N1—C6—C8—C7	17.1 (4)	C12—C11—C16—C15	0.3 (5)
C5—C6—C8—C7	−162.1 (3)	C7—C11—C16—C15	−177.5 (3)
O2—C7—C8—C17	88.2 (3)	C14—C15—C16—C11	0.9 (6)
C11—C7—C8—C17	−33.8 (4)	C5—C6—N1—O2	179.0 (3)
O2—C7—C8—C6	−26.0 (3)	C8—C6—N1—O2	−0.2 (4)
C11—C7—C8—C6	−148.0 (3)	C5—C10—O1—C9	18.8 (5)
O2—C7—C8—C9	−141.0 (3)	C1—C10—O1—C9	−162.1 (3)
C11—C7—C8—C9	97.0 (4)	C8—C9—O1—C10	−47.8 (4)
C17—C8—C9—O1	−62.8 (4)	C6—N1—O2—C7	−18.5 (4)
C6—C8—C9—O1	56.1 (4)	C11—C7—O2—N1	155.3 (3)
C7—C8—C9—O1	166.2 (3)	C8—C7—O2—N1	28.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2i	0.93	2.62	3.519 (5)	164
C15—H15···N2ii	0.93	2.61	3.334 (5)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2i	0.93	2.62	3.519 (5)	164
C15—H15⋯N2ii	0.93	2.61	3.334 (5)	135

Symmetry codes: (i) ; (ii) .