6,8-Di-bromo-3-nitro-2-phenyl-2H-chromene.

In the title compound, C15H9Br2NO3, the chromene unit is not quite planar (r.m.s. deviation from planarity = 0.0888 Å). The di-hydro-pyran ring adopts an envelope conformation with the phenyl-substituted C atom fused to the di-hydro-pyran ring as the flap. The dihedral angle between the plane defined by this C atom and the adjacent C and O atoms and the mean plane of the di-hydro-pyran ring excluding the phenyl-substituted C atom is 25.1 (3)°. The dihedral angle between the mean plane of the chromene unit and the phenyl ring is 85.7 (1)°. The crystal structure features C-H⋯O hydrogen bonds and Br⋯O contacts [3.289 (3) Å] involving the nitro O atoms.

Related literature

For the preparation of analogs of the title compound, see: Yan et al. (2001 ▶); Pateliya et al. (2009 ▶). For synthetic uses of the analogs and bioactive derivatives of the title compound, see: Furuta et al. (2007 ▶); Pateliya et al. (2009 ▶).

Experimental

Crystal data

C15H9Br2NO3

M = 411.05

Triclinic,

a = 8.2249 (19) Å

b = 8.886 (2) Å

c = 10.814 (3) Å

α = 73.503 (4)°

β = 75.633 (4)°

γ = 79.579 (4)°

V = 728.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 5.57 mm−1

T = 296 K

0.37 × 0.24 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.232, T max = 0.505

3687 measured reflections

2563 independent reflections

1856 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.105

S = 1.04

2563 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.56 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301221X/zl2545sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301221X/zl2545Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301221X/zl2545Isup3.cml

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

C15H9Br2NO3	F(000) = 400
Mr = 411.05	Dx = 1.873 Mg m−3
Triclinic, P1	Melting point: 358 K
a = 8.2249 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.886 (2) Å	Cell parameters from 1256 reflections
c = 10.814 (3) Å	θ = 2.6–23.4°
α = 73.503 (4)°	µ = 5.57 mm−1
β = 75.633 (4)°	T = 296 K
γ = 79.579 (4)°	Block, yellow
V = 728.8 (3) Å3	0.37 × 0.24 × 0.14 mm
Z = 2

Bruker APEXII CCD diffractometer	2563 independent reflections
Radiation source: fine-focus sealed tube	1856 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.232, Tmax = 0.505	k = −10→8
3687 measured reflections	l = −12→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0459P)2] where P = (Fo2 + 2Fc2)/3
2563 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.56 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	1.27050 (6)	0.90953 (6)	0.84090 (5)	0.0643 (2)
Br2	0.93397 (8)	0.62857 (8)	1.35367 (5)	0.0800 (2)
N1	0.6350 (4)	0.6139 (4)	0.7380 (4)	0.0480 (9)
O1	0.6475 (4)	0.6655 (5)	0.6195 (3)	0.0686 (10)
O2	0.5354 (4)	0.5232 (4)	0.8073 (3)	0.0699 (10)
O3	1.0007 (3)	0.7836 (3)	0.7672 (3)	0.0431 (7)
C1	0.9785 (5)	0.7523 (5)	0.8998 (4)	0.0377 (9)
C2	1.0929 (5)	0.7996 (5)	0.9515 (4)	0.0441 (10)
C3	1.0787 (5)	0.7621 (5)	1.0868 (4)	0.0521 (12)
H3	1.1558	0.7935	1.1216	0.063*
C4	0.9514 (5)	0.6788 (5)	1.1700 (4)	0.0494 (11)
C5	0.8386 (5)	0.6283 (5)	1.1199 (4)	0.0449 (10)
H5	0.7545	0.5694	1.1763	0.054*
C6	0.8516 (5)	0.6659 (5)	0.9847 (4)	0.0390 (10)
C7	0.7392 (5)	0.6132 (5)	0.9260 (4)	0.0409 (10)
H7	0.6635	0.5423	0.9776	0.049*
C8	0.7458 (5)	0.6672 (5)	0.7984 (4)	0.0382 (9)
C9	0.8570 (5)	0.7858 (5)	0.7090 (4)	0.0375 (9)
H9	0.9015	0.7541	0.6261	0.045*
C10	0.7659 (5)	0.9503 (5)	0.6771 (4)	0.0396 (10)
C11	0.7715 (6)	1.0345 (6)	0.5490 (5)	0.0570 (12)
H11	0.8330	0.9893	0.4812	0.068*
C12	0.6882 (7)	1.1838 (7)	0.5188 (5)	0.0702 (15)
H12	0.6930	1.2391	0.4311	0.084*
C13	0.5985 (6)	1.2509 (6)	0.6174 (6)	0.0680 (15)
H13	0.5422	1.3526	0.5972	0.082*
C14	0.5908 (6)	1.1686 (6)	0.7473 (5)	0.0576 (13)
H14	0.5293	1.2144	0.8148	0.069*
C15	0.6736 (5)	1.0198 (5)	0.7763 (4)	0.0447 (10)
H15	0.6680	0.9643	0.8640	0.054*

	U11	U22	U33	U12	U13	U23
Br1	0.0462 (3)	0.0659 (4)	0.0820 (4)	−0.0181 (2)	−0.0097 (2)	−0.0162 (3)
Br2	0.0990 (4)	0.0991 (5)	0.0454 (3)	0.0001 (4)	−0.0277 (3)	−0.0197 (3)
N1	0.046 (2)	0.050 (2)	0.052 (3)	−0.0092 (18)	−0.0085 (19)	−0.020 (2)
O1	0.076 (2)	0.092 (3)	0.046 (2)	−0.024 (2)	−0.0183 (18)	−0.0163 (19)
O2	0.071 (2)	0.085 (3)	0.066 (2)	−0.045 (2)	−0.0055 (18)	−0.023 (2)
O3	0.0343 (14)	0.0536 (18)	0.0381 (17)	−0.0051 (13)	−0.0062 (12)	−0.0077 (14)
C1	0.034 (2)	0.037 (2)	0.041 (3)	0.0003 (18)	−0.0100 (18)	−0.0078 (19)
C2	0.036 (2)	0.041 (2)	0.056 (3)	0.0031 (19)	−0.012 (2)	−0.015 (2)
C3	0.050 (3)	0.056 (3)	0.059 (3)	0.003 (2)	−0.022 (2)	−0.024 (3)
C4	0.050 (3)	0.053 (3)	0.044 (3)	0.007 (2)	−0.014 (2)	−0.016 (2)
C5	0.043 (2)	0.045 (3)	0.041 (3)	−0.001 (2)	−0.008 (2)	−0.006 (2)
C6	0.041 (2)	0.038 (2)	0.038 (2)	−0.0024 (18)	−0.0117 (19)	−0.0065 (19)
C7	0.040 (2)	0.036 (2)	0.045 (3)	−0.0062 (18)	−0.0043 (19)	−0.011 (2)
C8	0.036 (2)	0.040 (2)	0.040 (3)	−0.0041 (18)	−0.0053 (19)	−0.015 (2)
C9	0.037 (2)	0.046 (3)	0.032 (2)	−0.0069 (18)	−0.0066 (18)	−0.0113 (19)
C10	0.036 (2)	0.044 (2)	0.041 (3)	−0.0084 (19)	−0.0094 (19)	−0.010 (2)
C11	0.060 (3)	0.060 (3)	0.043 (3)	−0.002 (2)	−0.010 (2)	−0.005 (2)
C12	0.076 (3)	0.070 (4)	0.053 (3)	0.004 (3)	−0.019 (3)	−0.001 (3)
C13	0.063 (3)	0.046 (3)	0.090 (5)	0.003 (3)	−0.032 (3)	−0.001 (3)
C14	0.055 (3)	0.050 (3)	0.073 (4)	−0.001 (2)	−0.016 (3)	−0.024 (3)
C15	0.044 (2)	0.043 (3)	0.048 (3)	−0.007 (2)	−0.010 (2)	−0.011 (2)

Br1—C2	1.872 (4)	C7—C8	1.316 (5)
Br2—C4	1.882 (4)	C7—H7	0.9300
N1—O2	1.214 (4)	C8—C9	1.487 (6)
N1—O1	1.217 (4)	C9—C10	1.504 (5)
N1—C8	1.453 (5)	C9—H9	0.9800
O3—C1	1.352 (5)	C10—C11	1.369 (6)
O3—C9	1.465 (4)	C10—C15	1.382 (6)
C1—C2	1.384 (6)	C11—C12	1.368 (7)
C1—C6	1.391 (6)	C11—H11	0.9300
C2—C3	1.385 (6)	C12—C13	1.360 (7)
C3—C4	1.373 (6)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.380 (6)
C4—C5	1.376 (6)	C13—H13	0.9300
C5—C6	1.385 (5)	C14—C15	1.362 (6)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.447 (6)	C15—H15	0.9300
O2—N1—O1	124.0 (4)	C7—C8—C9	124.5 (4)
O2—N1—C8	119.0 (4)	N1—C8—C9	116.0 (4)
O1—N1—C8	116.9 (4)	O3—C9—C8	109.5 (3)
C1—O3—C9	119.2 (3)	O3—C9—C10	110.4 (3)
O3—C1—C2	118.3 (4)	C8—C9—C10	113.3 (3)
O3—C1—C6	122.2 (3)	O3—C9—H9	107.8
C2—C1—C6	119.4 (4)	C8—C9—H9	107.8
C1—C2—C3	119.7 (4)	C10—C9—H9	107.8
C1—C2—Br1	120.9 (3)	C11—C10—C15	118.4 (4)
C3—C2—Br1	119.4 (3)	C11—C10—C9	120.7 (4)
C4—C3—C2	120.5 (4)	C15—C10—C9	120.9 (4)
C4—C3—H3	119.7	C10—C11—C12	121.3 (5)
C2—C3—H3	119.7	C10—C11—H11	119.4
C3—C4—C5	120.5 (4)	C12—C11—H11	119.4
C3—C4—Br2	120.0 (3)	C13—C12—C11	119.7 (5)
C5—C4—Br2	119.6 (4)	C13—C12—H12	120.1
C4—C5—C6	119.4 (4)	C11—C12—H12	120.1
C4—C5—H5	120.3	C12—C13—C14	120.1 (5)
C6—C5—H5	120.3	C12—C13—H13	119.9
C5—C6—C1	120.6 (4)	C14—C13—H13	119.9
C5—C6—C7	121.9 (4)	C15—C14—C13	119.7 (5)
C1—C6—C7	117.4 (4)	C15—C14—H14	120.2
C8—C7—C6	118.9 (4)	C13—C14—H14	120.2
C8—C7—H7	120.6	C14—C15—C10	120.8 (4)
C6—C7—H7	120.6	C14—C15—H15	119.6
C7—C8—N1	119.4 (4)	C10—C15—H15	119.6
C9—O3—C1—C2	−159.3 (3)	O2—N1—C8—C7	1.8 (6)
C9—O3—C1—C6	24.9 (5)	O1—N1—C8—C7	−179.0 (4)
O3—C1—C2—C3	−176.7 (3)	O2—N1—C8—C9	−176.3 (3)
C6—C1—C2—C3	−0.7 (6)	O1—N1—C8—C9	2.8 (5)
O3—C1—C2—Br1	1.8 (5)	C1—O3—C9—C8	−33.4 (5)
C6—C1—C2—Br1	177.7 (3)	C1—O3—C9—C10	92.0 (4)
C1—C2—C3—C4	−0.3 (6)	C7—C8—C9—O3	23.2 (5)
Br1—C2—C3—C4	−178.7 (3)	N1—C8—C9—O3	−158.8 (3)
C2—C3—C4—C5	1.5 (6)	C7—C8—C9—C10	−100.6 (4)
C2—C3—C4—Br2	179.9 (3)	N1—C8—C9—C10	77.5 (4)
C3—C4—C5—C6	−1.8 (6)	O3—C9—C10—C11	110.8 (4)
Br2—C4—C5—C6	179.8 (3)	C8—C9—C10—C11	−126.0 (4)
C4—C5—C6—C1	0.8 (6)	O3—C9—C10—C15	−69.7 (5)
C4—C5—C6—C7	178.6 (4)	C8—C9—C10—C15	53.5 (5)
O3—C1—C6—C5	176.3 (3)	C15—C10—C11—C12	0.0 (7)
C2—C1—C6—C5	0.4 (6)	C9—C10—C11—C12	179.5 (5)
O3—C1—C6—C7	−1.6 (5)	C10—C11—C12—C13	0.2 (8)
C2—C1—C6—C7	−177.4 (4)	C11—C12—C13—C14	−0.3 (8)
C5—C6—C7—C8	172.6 (4)	C12—C13—C14—C15	0.1 (7)
C1—C6—C7—C8	−9.6 (6)	C13—C14—C15—C10	0.2 (7)
C6—C7—C8—N1	179.3 (3)	C11—C10—C15—C14	−0.3 (6)
C6—C7—C8—C9	−2.7 (6)	C9—C10—C15—C14	−179.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.93	2.61	3.404	144
C7—H7···O2i	0.93	2.47	3.265	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.93	2.61	3.404	144
C7—H7⋯O2i	0.93	2.47	3.265	143

Symmetry code: (i) .