2-(4-Bromo-phen-yl)-6-methyl-4H-1-benzopyran-4-one (4'-bromo-6-methyl-flavone).

Planar (r.m.s. deviation from the plane through all non-H atoms = 0.036 Å) mol-ecules of the title compound, C(16)H(11)BrO(2), form a layered structure stabilized by C-H⋯O hydrogen bonds and π-π stacking inter-actions.

Related literature

For background information on flavones and their properties, see: Hsiao et al. (2007 ▶); Manthey et al. (2001 ▶); Middleton et al. (2000 ▶). Millot et al. (2009 ▶); Moulari et al. (2006 ▶); Ren et al. (2003 ▶); Moon et al. (2007 ▶). For related structures, see: Kumar et al. (1998 ▶); Artali et al. (2003 ▶); Białońska et al. (2007 ▶); Ghalib et al. (2010 ▶).

Experimental

Crystal data

C16H11BrO2

M = 315.16

Monoclinic,

a = 13.759 (3) Å

b = 6.873 (2) Å

c = 13.460 (2) Å

β = 90.25 (3)°

V = 1272.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.22 mm−1

T = 100 K

0.31 × 0.29 × 0.04 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.474, T max = 0.893

25822 measured reflections

5962 independent reflections

3659 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.070

S = 0.88

5962 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010718/ds2025sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010718/ds2025Isup2.hkl

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

C16H11BrO2	F(000) = 632
Mr = 315.16	Dx = 1.645 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11464 reflections
a = 13.759 (3) Å	θ = 3.0–36.9°
b = 6.873 (2) Å	µ = 3.22 mm−1
c = 13.460 (2) Å	T = 100 K
β = 90.25 (3)°	Plate, colorless
V = 1272.8 (5) Å3	0.31 × 0.29 × 0.04 mm
Z = 4

Kuma KM-4-CCD diffractometer	5962 independent reflections
Radiation source: fine-focus sealed tube	3659 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scan	θmax = 36.0°, θmin = 3.0°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009); analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	h = −22→22
Tmin = 0.474, Tmax = 0.893	k = −11→10
25822 measured reflections	l = −21→22

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.0385P)2] where P = (Fo2 + 2Fc2)/3
5962 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET) (compiled May 29 2009,17:40:42) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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 > 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
Br	0.122301 (8)	0.12666 (2)	0.048602 (10)	0.02299 (4)
O1	0.59232 (6)	0.12638 (15)	0.20324 (6)	0.01526 (15)
C2	0.51619 (8)	0.12091 (19)	0.26748 (8)	0.01346 (19)
C3	0.52887 (8)	0.1170 (2)	0.36736 (8)	0.0158 (2)
H3A	0.4733	0.1138	0.4089	0.019*
O4	0.63780 (7)	0.11445 (16)	0.50391 (6)	0.02132 (18)
C4	0.62442 (8)	0.1176 (2)	0.41278 (9)	0.0152 (2)
C5	0.80289 (8)	0.1197 (2)	0.37337 (9)	0.0158 (2)
H5A	0.8173	0.1160	0.4424	0.019*
C6	0.87838 (8)	0.1235 (2)	0.30587 (9)	0.0173 (2)
C7	0.85504 (9)	0.1311 (2)	0.20364 (9)	0.0188 (2)
H7A	0.9062	0.1348	0.1565	0.023*
C8	0.76018 (9)	0.1335 (2)	0.17014 (9)	0.0179 (2)
H8A	0.7459	0.1396	0.1011	0.021*
C9	0.70523 (8)	0.1212 (2)	0.34182 (8)	0.01366 (19)
C10	0.68548 (8)	0.1267 (2)	0.24016 (9)	0.01469 (19)
C11	0.42181 (8)	0.12034 (19)	0.21497 (8)	0.01378 (19)
C12	0.41819 (9)	0.1370 (2)	0.11092 (9)	0.0170 (2)
H12A	0.4768	0.1477	0.0743	0.020*
C13	0.32929 (9)	0.1380 (2)	0.06124 (9)	0.0181 (2)
H13A	0.3269	0.1486	−0.0091	0.022*
C14	0.24418 (8)	0.1234 (2)	0.11563 (9)	0.0169 (2)
C15	0.24576 (9)	0.1070 (2)	0.21903 (10)	0.0184 (2)
H15A	0.1869	0.0980	0.2553	0.022*
C16	0.33448 (9)	0.1041 (2)	0.26785 (9)	0.0166 (2)
H16A	0.3363	0.0910	0.3381	0.020*
C17	0.98418 (9)	0.1213 (2)	0.33957 (10)	0.0217 (2)
H17A	0.9871	0.1160	0.4123	0.033*
H17B	1.0167	0.2396	0.3163	0.033*
H17C	1.0168	0.0069	0.3118	0.033*

	U11	U22	U33	U12	U13	U23
Br	0.01513 (6)	0.02745 (7)	0.02633 (7)	0.00270 (6)	−0.00771 (4)	−0.00266 (6)
O1	0.0108 (3)	0.0227 (4)	0.0123 (3)	−0.0008 (4)	−0.0008 (3)	0.0003 (4)
C2	0.0130 (4)	0.0128 (5)	0.0145 (5)	−0.0002 (5)	0.0009 (4)	0.0007 (5)
C3	0.0135 (4)	0.0200 (5)	0.0139 (5)	−0.0007 (5)	0.0013 (4)	0.0001 (5)
O4	0.0200 (4)	0.0308 (5)	0.0132 (4)	−0.0045 (4)	−0.0010 (3)	0.0008 (4)
C4	0.0155 (5)	0.0155 (5)	0.0145 (5)	−0.0015 (5)	−0.0006 (4)	0.0003 (5)
C5	0.0146 (5)	0.0159 (5)	0.0169 (5)	−0.0008 (5)	−0.0031 (4)	−0.0006 (5)
C6	0.0128 (4)	0.0177 (5)	0.0215 (5)	−0.0009 (5)	−0.0020 (4)	−0.0009 (5)
C7	0.0137 (5)	0.0232 (6)	0.0195 (5)	−0.0004 (5)	0.0019 (4)	−0.0014 (6)
C8	0.0147 (5)	0.0239 (6)	0.0150 (5)	−0.0004 (5)	0.0004 (4)	−0.0012 (5)
C9	0.0124 (4)	0.0143 (5)	0.0144 (5)	−0.0010 (5)	−0.0005 (4)	0.0002 (5)
C10	0.0115 (4)	0.0157 (5)	0.0168 (5)	−0.0008 (5)	−0.0012 (4)	−0.0007 (5)
C11	0.0122 (4)	0.0138 (5)	0.0154 (5)	−0.0001 (5)	−0.0015 (4)	−0.0002 (5)
C12	0.0149 (5)	0.0191 (6)	0.0171 (5)	−0.0007 (5)	−0.0005 (4)	0.0017 (5)
C13	0.0178 (5)	0.0195 (6)	0.0170 (5)	−0.0008 (5)	−0.0031 (4)	0.0008 (5)
C14	0.0144 (5)	0.0160 (5)	0.0203 (5)	0.0017 (5)	−0.0046 (4)	−0.0008 (5)
C15	0.0139 (5)	0.0196 (6)	0.0216 (6)	0.0003 (5)	−0.0001 (4)	−0.0012 (5)
C16	0.0138 (5)	0.0198 (6)	0.0163 (5)	−0.0001 (5)	0.0000 (4)	−0.0002 (5)
C17	0.0140 (5)	0.0270 (6)	0.0240 (6)	0.0002 (6)	−0.0036 (4)	−0.0022 (6)

Br—C14	1.9008 (13)	C8—C10	1.3983 (16)
O1—C2	1.3617 (14)	C8—H8A	0.9500
O1—C10	1.3727 (14)	C9—C10	1.3944 (16)
C2—C3	1.3551 (16)	C11—C16	1.4036 (17)
C2—C11	1.4757 (16)	C11—C12	1.4059 (16)
C3—C4	1.4475 (17)	C12—C13	1.3914 (17)
C3—H3A	0.9500	C12—H12A	0.9500
O4—C4	1.2397 (15)	C13—C14	1.3875 (17)
C4—C9	1.4692 (16)	C13—H13A	0.9500
C5—C6	1.3832 (17)	C14—C15	1.3964 (18)
C5—C9	1.4075 (16)	C15—C16	1.3839 (17)
C5—H5A	0.9500	C15—H15A	0.9500
C6—C7	1.4126 (18)	C16—H16A	0.9500
C6—C17	1.5228 (17)	C17—H17A	0.9800
C7—C8	1.3792 (17)	C17—H17B	0.9800
C7—H7A	0.9500	C17—H17C	0.9800
C2—O1—C10	119.33 (9)	O1—C10—C8	116.36 (10)
C3—C2—O1	122.30 (10)	C9—C10—C8	121.44 (10)
C3—C2—C11	125.75 (11)	C16—C11—C12	119.01 (11)
O1—C2—C11	111.95 (9)	C16—C11—C2	120.72 (10)
C2—C3—C4	122.12 (11)	C12—C11—C2	120.27 (10)
C2—C3—H3A	118.9	C13—C12—C11	120.42 (11)
C4—C3—H3A	118.9	C13—C12—H12A	119.8
O4—C4—C3	123.27 (11)	C11—C12—H12A	119.8
O4—C4—C9	122.28 (11)	C14—C13—C12	119.23 (11)
C3—C4—C9	114.45 (10)	C14—C13—H13A	120.4
C6—C5—C9	121.35 (11)	C12—C13—H13A	120.4
C6—C5—H5A	119.3	C13—C14—C15	121.48 (11)
C9—C5—H5A	119.3	C13—C14—Br	119.58 (9)
C5—C6—C7	118.19 (11)	C15—C14—Br	118.94 (9)
C5—C6—C17	121.59 (11)	C16—C15—C14	118.97 (12)
C7—C6—C17	120.23 (11)	C16—C15—H15A	120.5
C8—C7—C6	121.99 (11)	C14—C15—H15A	120.5
C8—C7—H7A	119.0	C15—C16—C11	120.88 (12)
C6—C7—H7A	119.0	C15—C16—H16A	119.6
C7—C8—C10	118.46 (11)	C11—C16—H16A	119.6
C7—C8—H8A	120.8	C6—C17—H17A	109.5
C10—C8—H8A	120.8	C6—C17—H17B	109.5
C10—C9—C5	118.56 (10)	H17A—C17—H17B	109.5
C10—C9—C4	119.58 (10)	C6—C17—H17C	109.5
C5—C9—C4	121.87 (10)	H17A—C17—H17C	109.5
O1—C10—C9	122.20 (10)	H17B—C17—H17C	109.5
C10—O1—C2—C3	0.45 (19)	C4—C9—C10—O1	−0.9 (2)
C10—O1—C2—C11	−179.69 (13)	C5—C9—C10—C8	−0.9 (2)
O1—C2—C3—C4	−0.3 (2)	C4—C9—C10—C8	178.91 (13)
C11—C2—C3—C4	179.90 (13)	C7—C8—C10—O1	−179.04 (14)
C2—C3—C4—O4	179.89 (13)	C7—C8—C10—C9	1.2 (2)
C2—C3—C4—C9	−0.5 (2)	C3—C2—C11—C16	−3.7 (2)
C9—C5—C6—C7	0.7 (2)	O1—C2—C11—C16	176.44 (12)
C9—C5—C6—C17	−179.82 (14)	C3—C2—C11—C12	175.99 (13)
C5—C6—C7—C8	−0.4 (2)	O1—C2—C11—C12	−3.86 (18)
C17—C6—C7—C8	−179.95 (14)	C16—C11—C12—C13	0.2 (2)
C6—C7—C8—C10	−0.5 (2)	C2—C11—C12—C13	−179.51 (13)
C6—C5—C9—C10	0.0 (2)	C11—C12—C13—C14	0.3 (2)
C6—C5—C9—C4	−179.84 (13)	C12—C13—C14—C15	−0.2 (2)
O4—C4—C9—C10	−179.34 (13)	C12—C13—C14—Br	179.51 (11)
C3—C4—C9—C10	1.0 (2)	C13—C14—C15—C16	−0.4 (2)
O4—C4—C9—C5	0.5 (2)	Br—C14—C15—C16	179.84 (11)
C3—C4—C9—C5	−179.17 (13)	C14—C15—C16—C11	1.0 (2)
C2—O1—C10—C9	0.1 (2)	C12—C11—C16—C15	−0.8 (2)
C2—O1—C10—C8	−179.67 (12)	C2—C11—C16—C15	178.85 (14)
C5—C9—C10—O1	179.28 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4i	0.95	2.49	3.2904 (17)	142
C16—H16A···O4i	0.95	2.58	3.4394 (16)	151

Cg(I)	Cg(J)	Cg–Cg	Alpha	CgI_perp	CgJ_Perp	Slippage
Cg(1)	Cg(2)i	3.895	7.13 (3)	3.579 (2)	-3.430 (2)	1.84
Cg(1)	Cg(2)ii	3.843	7.13 (3)	-3.266 (2)	3.438 (2)	1.72

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4i	0.95	2.49	3.2904 (17)	142
C16—H16A⋯O4i	0.95	2.58	3.4394 (16)	151

Symmetry code: (i) .

Table 2

π–π inter­actions (Å, °)

Cg(1) and Cg(2) are the centroids of the C5–C10 and C11–C16 rings, respectively.

Cg(I)	Cg(J)	Cg–Cg	Alpha	CgI_perp	CgJ_Perp	Slippage
Cg(1)	Cg(2)i	3.895	7.13 (3)	3.579 (2)	−3.430 (2)	1.84
Cg(1)	Cg(2)ii	3.843	7.13 (3)	−3.266 (2)	3.438 (2)	1.72

Notes: Cg–Cg = distance between ring centroids; Alpha = dihedral angle between planes I and J; CgI_Perp = perpendicular distance of Cg(I) on ring J; CgJ_Perp = perpendicular distance of Cg(J) on ring I; Slippage = distance between Cg(I) and perpendicular projection of Cg(J) on Ring I. Symmetry codes: (i) ; (ii) .