3-(3-Bromo-4-methoxy-phen-yl)-1,5-diphenyl-pentane-1,5-dione.

In the title compound, C(24)H(21)BrO(3), the central bromo-methoxy-benzene ring forms dihedral angles of 63.6 (1) and 60.3 (1)° with the terminal phenyl rings, while the angle between the two phenyl rings is 25.8 (1)°. The crystal structure is stabilized by weak C-H⋯Br and C-H⋯O hydrogen bonds, and C-H⋯π and π-π stacking [centroid-centroid distance = 3.910 (3) Å] inter-actions.

Related literature

For 1,5-diketones, see: Hirsch & Bailey (1978 ▶). For related structures, see: Das et al. (1994 ▶); He et al. (2008 ▶); Li et al. (2008 ▶); Teh et al. (2006 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C24H21BrO3

M = 437.32

Monoclinic,

a = 12.7305 (4) Å

b = 7.14024 (19) Å

c = 22.8133 (8) Å

β = 105.602 (3)°

V = 1997.28 (11) Å3

Z = 4

Mo Kα radiation

μ = 2.08 mm−1

T = 100 K

0.5 × 0.5 × 0.3 mm

Data collection

Oxford Diffraction Xcalibur Eos CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.471, T max = 0.536

7645 measured reflections

4094 independent reflections

3289 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.057

S = 1.00

4094 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶) and SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008548/is2528sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008548/is2528Isup2.hkl

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

C24H21BrO3	F(000) = 896
Mr = 437.32	Dx = 1.454 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5038 reflections
a = 12.7305 (4) Å	θ = 3.0–28.0°
b = 7.14024 (19) Å	µ = 2.08 mm−1
c = 22.8133 (8) Å	T = 100 K
β = 105.602 (3)°	Block, yellow
V = 1997.28 (11) Å3	0.5 × 0.5 × 0.3 mm
Z = 4

Oxford Diffraction Xcalibur Eos CCD diffractometer	4094 independent reflections
Radiation source: fine-focus sealed tube	3289 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 16.1544 pixels mm-1	θmax = 28.1°, θmin = 3.0°
ω scan	h = −12→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→8
Tmin = 0.471, Tmax = 0.536	l = −25→27
7645 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0327P)2] where P = (Fo2 + 2Fc2)/3
4094 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.91462 (13)	0.0724 (2)	0.35970 (8)	0.0145 (4)
O1	0.86814 (9)	0.01848 (17)	0.39695 (5)	0.0217 (3)
C2	0.85537 (13)	0.0764 (2)	0.29248 (7)	0.0134 (4)
H2A	0.7862	0.0060	0.2862	0.016*
H2B	0.9006	0.0104	0.2698	0.016*
C3	0.82916 (13)	0.2738 (2)	0.26526 (8)	0.0131 (4)
H3A	0.8993	0.3445	0.2726	0.016*
C4	0.77919 (13)	0.2605 (3)	0.19628 (8)	0.0145 (4)
H4A	0.7216	0.1633	0.1880	0.017*
H4B	0.7440	0.3815	0.1815	0.017*
O5	0.95755 (9)	0.19514 (16)	0.18610 (5)	0.0191 (3)
C5	0.86066 (14)	0.2138 (2)	0.16057 (8)	0.0145 (4)
C11	1.03092 (13)	0.1341 (2)	0.37984 (8)	0.0149 (4)
C12	1.08947 (14)	0.1805 (2)	0.33810 (9)	0.0185 (4)
H12A	1.0549	0.1775	0.2957	0.022*
C13	1.19792 (14)	0.2310 (3)	0.35891 (10)	0.0261 (5)
H13A	1.2377	0.2622	0.3305	0.031*
C14	1.24952 (15)	0.2366 (3)	0.42059 (10)	0.0296 (5)
H14A	1.3241	0.2716	0.4344	0.035*
C15	1.19147 (15)	0.1907 (2)	0.46233 (10)	0.0294 (5)
H15A	1.2262	0.1945	0.5047	0.035*
C16	1.08349 (14)	0.1398 (2)	0.44186 (9)	0.0209 (4)
H16A	1.0442	0.1082	0.4705	0.025*
C31	0.75354 (13)	0.3834 (2)	0.29399 (7)	0.0121 (4)
C32	0.64779 (13)	0.3198 (2)	0.28958 (7)	0.0137 (4)
H32A	0.6240	0.2031	0.2706	0.016*
C33	0.57781 (12)	0.4268 (2)	0.31288 (7)	0.0125 (4)
Br33	0.435504 (13)	0.33429 (2)	0.306668 (9)	0.01938 (6)
O34	0.53210 (9)	0.69501 (16)	0.36041 (6)	0.0191 (3)
C34	0.60856 (13)	0.5983 (2)	0.34074 (8)	0.0139 (4)
C35	0.71445 (13)	0.6593 (2)	0.34608 (8)	0.0145 (4)
H35A	0.7388	0.7746	0.3659	0.017*
C36	0.78462 (13)	0.5528 (2)	0.32272 (7)	0.0138 (4)
H36A	0.8564	0.5976	0.3266	0.017*
C51	0.81896 (14)	0.1985 (2)	0.09296 (8)	0.0155 (4)
C52	0.70940 (15)	0.2171 (2)	0.06268 (8)	0.0209 (4)
H52A	0.6576	0.2364	0.0853	0.025*
C53	0.67473 (16)	0.2080 (3)	−0.00028 (9)	0.0266 (5)
H53A	0.5995	0.2212	−0.0207	0.032*
C54	0.75009 (16)	0.1794 (2)	−0.03336 (8)	0.0254 (4)
H54A	0.7267	0.1756	−0.0766	0.031*
C55	0.85911 (16)	0.1566 (2)	−0.00367 (8)	0.0238 (4)
H55A	0.9103	0.1338	−0.0264	0.029*
C56	0.89418 (15)	0.1669 (2)	0.05928 (8)	0.0187 (4)
H56A	0.9694	0.1525	0.0795	0.022*
C341	0.55832 (15)	0.8827 (2)	0.38057 (10)	0.0272 (5)
H34D	0.4945	0.9417	0.3891	0.041*
H34A	0.5795	0.9535	0.3488	0.041*
H34B	0.6189	0.8817	0.4177	0.041*

	U11	U22	U33	U12	U13	U23
C1	0.0172 (9)	0.0083 (8)	0.0187 (9)	0.0011 (7)	0.0057 (7)	−0.0009 (7)
O1	0.0261 (7)	0.0242 (7)	0.0172 (7)	−0.0093 (6)	0.0099 (5)	−0.0017 (6)
C2	0.0119 (8)	0.0158 (9)	0.0136 (9)	−0.0011 (7)	0.0052 (7)	−0.0013 (7)
C3	0.0104 (8)	0.0148 (8)	0.0149 (9)	−0.0019 (7)	0.0046 (7)	−0.0002 (7)
C4	0.0133 (8)	0.0162 (9)	0.0144 (9)	0.0002 (8)	0.0041 (7)	0.0009 (8)
O5	0.0147 (6)	0.0265 (7)	0.0168 (6)	0.0010 (6)	0.0056 (5)	0.0000 (5)
C5	0.0168 (9)	0.0110 (8)	0.0162 (9)	−0.0015 (7)	0.0055 (7)	0.0010 (7)
C11	0.0162 (9)	0.0073 (8)	0.0202 (9)	0.0018 (7)	0.0034 (7)	0.0000 (7)
C12	0.0156 (9)	0.0141 (9)	0.0254 (10)	0.0021 (8)	0.0047 (7)	0.0020 (8)
C13	0.0158 (9)	0.0182 (10)	0.0455 (13)	0.0037 (8)	0.0104 (9)	0.0059 (10)
C14	0.0136 (9)	0.0190 (10)	0.0499 (14)	−0.0001 (9)	−0.0020 (9)	−0.0038 (10)
C15	0.0257 (11)	0.0205 (11)	0.0324 (12)	0.0047 (9)	−0.0086 (9)	−0.0059 (9)
C16	0.0225 (10)	0.0132 (9)	0.0254 (10)	0.0022 (8)	0.0036 (8)	0.0002 (8)
C31	0.0105 (8)	0.0152 (9)	0.0104 (8)	−0.0008 (7)	0.0026 (6)	0.0017 (7)
C32	0.0143 (8)	0.0137 (8)	0.0127 (8)	−0.0026 (8)	0.0031 (7)	−0.0010 (7)
C33	0.0068 (8)	0.0161 (9)	0.0142 (9)	−0.0004 (7)	0.0020 (6)	0.0055 (7)
Br33	0.00941 (9)	0.01879 (10)	0.03102 (11)	−0.00150 (8)	0.00730 (7)	−0.00147 (9)
O34	0.0175 (6)	0.0152 (6)	0.0267 (7)	0.0022 (5)	0.0098 (5)	−0.0034 (5)
C34	0.0131 (8)	0.0156 (8)	0.0131 (9)	0.0035 (8)	0.0040 (7)	0.0037 (7)
C35	0.0157 (8)	0.0118 (8)	0.0150 (9)	−0.0011 (8)	0.0028 (7)	−0.0003 (7)
C36	0.0094 (8)	0.0177 (9)	0.0141 (9)	−0.0036 (7)	0.0028 (7)	0.0021 (7)
C51	0.0200 (9)	0.0114 (9)	0.0152 (9)	−0.0009 (7)	0.0050 (7)	−0.0003 (7)
C52	0.0222 (10)	0.0206 (10)	0.0197 (10)	0.0000 (8)	0.0051 (8)	−0.0015 (8)
C53	0.0266 (10)	0.0266 (11)	0.0215 (10)	0.0019 (9)	−0.0025 (8)	−0.0014 (9)
C54	0.0420 (12)	0.0200 (10)	0.0118 (9)	−0.0052 (9)	0.0030 (8)	−0.0007 (8)
C55	0.0344 (11)	0.0216 (10)	0.0184 (10)	−0.0075 (9)	0.0125 (8)	−0.0036 (9)
C56	0.0227 (9)	0.0169 (9)	0.0177 (9)	−0.0036 (8)	0.0075 (7)	−0.0013 (8)
C341	0.0241 (10)	0.0173 (10)	0.0423 (13)	0.0024 (8)	0.0124 (9)	−0.0073 (9)

C1—O1	1.2210 (19)	C31—C32	1.399 (2)
C1—C11	1.494 (2)	C32—C33	1.384 (2)
C1—C2	1.516 (2)	C32—H32A	0.9500
C2—C3	1.540 (2)	C33—C34	1.387 (2)
C2—H2A	0.9900	C33—Br33	1.8975 (15)
C2—H2B	0.9900	O34—C34	1.3639 (19)
C3—C31	1.519 (2)	O34—C341	1.427 (2)
C3—C4	1.533 (2)	C34—C35	1.390 (2)
C3—H3A	1.0000	C35—C36	1.384 (2)
C4—C5	1.518 (2)	C35—H35A	0.9500
C4—H4A	0.9900	C36—H36A	0.9500
C4—H4B	0.9900	C51—C52	1.386 (2)
O5—C5	1.2214 (19)	C51—C56	1.398 (2)
C5—C51	1.494 (2)	C52—C53	1.386 (3)
C11—C16	1.394 (2)	C52—H52A	0.9500
C11—C12	1.398 (2)	C53—C54	1.386 (3)
C12—C13	1.382 (2)	C53—H53A	0.9500
C12—H12A	0.9500	C54—C55	1.381 (3)
C13—C14	1.384 (3)	C54—H54A	0.9500
C13—H13A	0.9500	C55—C56	1.386 (2)
C14—C15	1.392 (3)	C55—H55A	0.9500
C14—H14A	0.9500	C56—H56A	0.9500
C15—C16	1.376 (2)	C341—H34D	0.9800
C15—H15A	0.9500	C341—H34A	0.9800
C16—H16A	0.9500	C341—H34B	0.9800
C31—C36	1.382 (2)
O1—C1—C11	120.32 (16)	C36—C31—C3	121.46 (14)
O1—C1—C2	120.49 (15)	C32—C31—C3	120.72 (15)
C11—C1—C2	119.20 (14)	C33—C32—C31	119.98 (15)
C1—C2—C3	114.82 (13)	C33—C32—H32A	120.0
C1—C2—H2A	108.6	C31—C32—H32A	120.0
C3—C2—H2A	108.6	C32—C33—C34	122.15 (15)
C1—C2—H2B	108.6	C32—C33—Br33	118.64 (12)
C3—C2—H2B	108.6	C34—C33—Br33	119.20 (12)
H2A—C2—H2B	107.5	C34—O34—C341	117.10 (13)
C31—C3—C4	109.78 (13)	O34—C34—C33	117.34 (14)
C31—C3—C2	113.04 (13)	O34—C34—C35	125.00 (15)
C4—C3—C2	110.01 (14)	C33—C34—C35	117.66 (15)
C31—C3—H3A	107.9	C36—C35—C34	120.34 (16)
C4—C3—H3A	107.9	C36—C35—H35A	119.8
C2—C3—H3A	107.9	C34—C35—H35A	119.8
C5—C4—C3	114.18 (13)	C31—C36—C35	122.09 (15)
C5—C4—H4A	108.7	C31—C36—H36A	119.0
C3—C4—H4A	108.7	C35—C36—H36A	119.0
C5—C4—H4B	108.7	C52—C51—C56	119.20 (16)
C3—C4—H4B	108.7	C52—C51—C5	122.53 (15)
H4A—C4—H4B	107.6	C56—C51—C5	118.26 (15)
O5—C5—C51	121.14 (15)	C51—C52—C53	120.60 (17)
O5—C5—C4	121.06 (15)	C51—C52—H52A	119.7
C51—C5—C4	117.76 (14)	C53—C52—H52A	119.7
C16—C11—C12	119.09 (16)	C54—C53—C52	119.80 (18)
C16—C11—C1	119.11 (16)	C54—C53—H53A	120.1
C12—C11—C1	121.77 (16)	C52—C53—H53A	120.1
C13—C12—C11	119.63 (18)	C55—C54—C53	120.14 (17)
C13—C12—H12A	120.2	C55—C54—H54A	119.9
C11—C12—H12A	120.2	C53—C54—H54A	119.9
C12—C13—C14	120.94 (18)	C54—C55—C56	120.20 (17)
C12—C13—H13A	119.5	C54—C55—H55A	119.9
C14—C13—H13A	119.5	C56—C55—H55A	119.9
C13—C14—C15	119.63 (17)	C55—C56—C51	120.03 (17)
C13—C14—H14A	120.2	C55—C56—H56A	120.0
C15—C14—H14A	120.2	C51—C56—H56A	120.0
C16—C15—C14	119.69 (19)	O34—C341—H34D	109.5
C16—C15—H15A	120.2	O34—C341—H34A	109.5
C14—C15—H15A	120.2	H34D—C341—H34A	109.5
C15—C16—C11	121.02 (18)	O34—C341—H34B	109.5
C15—C16—H16A	119.5	H34D—C341—H34B	109.5
C11—C16—H16A	119.5	H34A—C341—H34B	109.5
C36—C31—C32	117.75 (15)
O1—C1—C2—C3	109.67 (17)	C31—C32—C33—C34	0.3 (2)
C11—C1—C2—C3	−70.76 (18)	C31—C32—C33—Br33	−179.41 (12)
C1—C2—C3—C31	−62.13 (18)	C341—O34—C34—C33	−170.80 (15)
C1—C2—C3—C4	174.75 (13)	C341—O34—C34—C35	8.7 (2)
C31—C3—C4—C5	160.56 (14)	C32—C33—C34—O34	177.99 (15)
C2—C3—C4—C5	−74.43 (17)	Br33—C33—C34—O34	−2.3 (2)
C3—C4—C5—O5	−2.1 (2)	C32—C33—C34—C35	−1.5 (2)
C3—C4—C5—C51	−179.88 (14)	Br33—C33—C34—C35	178.17 (12)
O1—C1—C11—C16	−3.8 (2)	O34—C34—C35—C36	−177.85 (15)
C2—C1—C11—C16	176.60 (15)	C33—C34—C35—C36	1.6 (2)
O1—C1—C11—C12	174.16 (15)	C32—C31—C36—C35	−0.7 (2)
C2—C1—C11—C12	−5.4 (2)	C3—C31—C36—C35	176.29 (15)
C16—C11—C12—C13	0.1 (2)	C34—C35—C36—C31	−0.5 (3)
C1—C11—C12—C13	−177.90 (16)	O5—C5—C51—C52	179.37 (16)
C11—C12—C13—C14	−0.2 (3)	C4—C5—C51—C52	−2.9 (2)
C12—C13—C14—C15	0.0 (3)	O5—C5—C51—C56	−1.6 (2)
C13—C14—C15—C16	0.2 (3)	C4—C5—C51—C56	176.14 (15)
C14—C15—C16—C11	−0.2 (3)	C56—C51—C52—C53	−1.1 (3)
C12—C11—C16—C15	0.1 (3)	C5—C51—C52—C53	177.88 (16)
C1—C11—C16—C15	178.16 (16)	C51—C52—C53—C54	0.2 (3)
C4—C3—C31—C36	−115.94 (17)	C52—C53—C54—C55	1.2 (3)
C2—C3—C31—C36	120.81 (17)	C53—C54—C55—C56	−1.7 (3)
C4—C3—C31—C32	61.0 (2)	C54—C55—C56—C51	0.7 (3)
C2—C3—C31—C32	−62.3 (2)	C52—C51—C56—C55	0.7 (3)
C36—C31—C32—C33	0.8 (2)	C5—C51—C56—C55	−178.35 (15)
C3—C31—C32—C33	−176.20 (15)

Cg1 is the centroid of the C31–C36 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Br33i	0.95	2.76	3.613 (2)	149
C35—H35A···O1ii	0.95	2.37	3.245 (2)	153
C36—H36A···O5iii	0.95	2.56	3.493 (2)	168
C54—H54A···Cg1iv	0.95	2.60	3.489 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Br33i	0.95	2.76	3.613 (2)	149
C35—H35A⋯O1ii	0.95	2.37	3.245 (2)	153
C36—H36A⋯O5iii	0.95	2.56	3.493 (2)	168
C54—H54A⋯Cg1iv	0.95	2.60	3.489 (3)	155

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