4-(2-Bromo-phen-yl)-2-phenyl-pyrano[3,2-c]chromen-5(4H)-one.

In the title compound, C24H15BrO3, the pyran-ochromenone ring is essentially planar, while the 2-bromo-phenyl group is almost perpendicular to it [85.58 (6)°]. In the crystal, inversion dimers linked by pairs of weak C-H⋯π bonds occur; there is also a short inter-atomic contact found between the Br and carbonyl O atoms [3.016 (1) Å].

Related literature

For coumarin chemistry and applications, see: Hinman et al. (1956 ▶); Soine (1964 ▶); Murray et al. (1982 ▶); Patil et al. (1993 ▶); Verotta et al. (2004 ▶); Heide (2009 ▶); Magolan et al. (2012 ▶). For related structures, see: Shi et al. (2004 ▶, 2005 ▶); Lakshmi et al. (2006 ▶). For related synthesis and structures, see: Naveen et al. (2007 ▶); Shaabani et al. (2008 ▶); Sarma et al. (2010 ▶); He et al. (2010 ▶).

Experimental

Crystal data

C24H15BrO3

M = 431.27

Monoclinic,

a = 11.5959 (2) Å

b = 17.7890 (4) Å

c = 8.7610 (2) Å

β = 97.060 (1)°

V = 1793.53 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.32 mm−1

T = 100 K

0.52 × 0.40 × 0.23 mm

Data collection

Bruker X8 APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.380, T max = 0.618

41256 measured reflections

4464 independent reflections

4019 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.068

S = 1.05

4464 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶) and WinGX (Farrugia,1999 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812044510/bv2211sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044510/bv2211Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812044510/bv2211Isup3.cml

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

C24H15BrO3	F(000) = 872
Mr = 431.27	Dx = 1.597 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9421 reflections
a = 11.5959 (2) Å	θ = 2.6–28.3°
b = 17.7890 (4) Å	µ = 2.32 mm−1
c = 8.7610 (2) Å	T = 100 K
β = 97.060 (1)°	Cuboidal, colourless
V = 1793.53 (7) Å3	0.52 × 0.40 × 0.23 mm
Z = 4

Bruker X8 APEXII KappaCCD diffractometer	4464 independent reflections
Radiation source: sealed tube	4019 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
Tmin = 0.380, Tmax = 0.618	k = −20→23
41256 measured reflections	l = −10→11

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0271P)2 + 1.4892P] where P = (Fo2 + 2Fc2)/3
4464 reflections	(Δ/σ)max = 0.003
253 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. Data collected on a Bruker X8 ApexII Kappa CCD diffractometer with 10 s/frame exposure time(total of 2250, width 0.5°)covering up to θ = 28.29° with 99.9% completeness accomplished.

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	0.771558 (15)	0.721619 (9)	0.11776 (2)	0.02123 (6)
O1	0.70255 (10)	1.05778 (6)	0.14190 (13)	0.0176 (2)
O2	0.55197 (11)	0.98739 (7)	−0.28387 (14)	0.0206 (2)
O3	0.59774 (12)	0.86907 (7)	−0.23016 (16)	0.0266 (3)
C1	0.65713 (13)	1.03040 (9)	0.00302 (18)	0.0152 (3)
C2	0.66299 (14)	0.95736 (9)	−0.03718 (19)	0.0170 (3)
C3	0.72297 (14)	0.89890 (9)	0.0691 (2)	0.0178 (3)
H3	0.6676	0.8565	0.0783	0.021*
C4	0.75403 (14)	0.93335 (10)	0.2258 (2)	0.0194 (3)
H4	0.7808	0.9008	0.3087	0.023*
C5	0.74635 (14)	1.00623 (9)	0.25547 (19)	0.0175 (3)
C6	0.77853 (15)	1.04556 (10)	0.40272 (19)	0.0192 (3)
C7	0.8584 (2)	1.01472 (12)	0.5172 (2)	0.0392 (5)
H7	0.8900	0.9663	0.5029	0.047*
C8	0.8922 (2)	1.05422 (13)	0.6525 (2)	0.0445 (6)
H8	0.9487	1.0332	0.7282	0.053*
C9	0.84469 (18)	1.12329 (12)	0.6777 (2)	0.0285 (4)
H9	0.8670	1.1497	0.7709	0.034*
C10	0.76475 (17)	1.15344 (12)	0.5665 (2)	0.0291 (4)
H10	0.7309	1.2009	0.5836	0.035*
C11	0.73243 (16)	1.11577 (11)	0.4291 (2)	0.0263 (4)
H11	0.6783	1.1382	0.3523	0.032*
C12	0.60043 (13)	1.08645 (9)	−0.09917 (18)	0.0155 (3)
C13	0.59292 (14)	1.16273 (9)	−0.06145 (19)	0.0173 (3)
H13	0.6272	1.1803	0.0361	0.021*
C14	0.53576 (15)	1.21245 (9)	−0.1660 (2)	0.0191 (3)
H14	0.5306	1.2641	−0.1404	0.023*
C15	0.48548 (15)	1.18643 (10)	−0.30964 (19)	0.0200 (3)
H15	0.4460	1.2208	−0.3809	0.024*
C16	0.49225 (15)	1.11142 (10)	−0.34978 (19)	0.0200 (3)
H16	0.4584	1.0940	−0.4477	0.024*
C17	0.54995 (14)	1.06213 (9)	−0.24295 (19)	0.0171 (3)
C18	0.60497 (14)	0.93349 (10)	−0.1856 (2)	0.0192 (3)
C19	0.83245 (14)	0.86731 (9)	0.0112 (2)	0.0189 (3)
C20	0.90660 (16)	0.91560 (10)	−0.0560 (2)	0.0266 (4)
H20	0.8870	0.9674	−0.0664	0.032*
C21	1.00623 (16)	0.89077 (11)	−0.1072 (2)	0.0260 (4)
H21	1.0541	0.9250	−0.1539	0.031*
C22	1.03834 (15)	0.81506 (11)	−0.0915 (2)	0.0251 (4)
H22	1.1076	0.7977	−0.1276	0.030*
C23	0.96779 (15)	0.76574 (10)	−0.0225 (2)	0.0217 (3)
H23	0.9890	0.7143	−0.0094	0.026*
C24	0.86588 (14)	0.79205 (9)	0.02731 (19)	0.0179 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.02278 (9)	0.01590 (9)	0.02471 (10)	0.00087 (6)	0.00178 (6)	0.00514 (6)
O1	0.0210 (6)	0.0138 (5)	0.0177 (5)	−0.0002 (4)	0.0007 (4)	−0.0012 (4)
O2	0.0245 (6)	0.0165 (6)	0.0206 (6)	−0.0026 (5)	0.0020 (5)	−0.0052 (5)
O3	0.0293 (7)	0.0169 (6)	0.0336 (7)	−0.0020 (5)	0.0035 (5)	−0.0096 (5)
C1	0.0134 (7)	0.0151 (7)	0.0177 (7)	−0.0021 (6)	0.0045 (6)	−0.0012 (6)
C2	0.0149 (7)	0.0154 (8)	0.0213 (8)	−0.0017 (6)	0.0055 (6)	−0.0016 (6)
C3	0.0175 (7)	0.0113 (7)	0.0257 (8)	−0.0009 (6)	0.0068 (6)	−0.0018 (6)
C4	0.0184 (8)	0.0173 (8)	0.0234 (8)	0.0008 (6)	0.0063 (6)	0.0022 (6)
C5	0.0159 (7)	0.0173 (8)	0.0200 (8)	0.0000 (6)	0.0052 (6)	0.0022 (6)
C6	0.0205 (8)	0.0192 (8)	0.0188 (8)	−0.0035 (6)	0.0062 (6)	0.0009 (6)
C7	0.0645 (15)	0.0242 (10)	0.0264 (10)	0.0119 (10)	−0.0043 (10)	0.0010 (8)
C8	0.0708 (17)	0.0355 (12)	0.0229 (10)	0.0075 (11)	−0.0110 (10)	0.0045 (9)
C9	0.0365 (10)	0.0325 (10)	0.0171 (8)	−0.0095 (8)	0.0061 (7)	−0.0026 (7)
C10	0.0247 (9)	0.0293 (10)	0.0332 (10)	−0.0007 (8)	0.0025 (7)	−0.0124 (8)
C11	0.0218 (9)	0.0263 (9)	0.0292 (9)	0.0029 (7)	−0.0027 (7)	−0.0078 (8)
C12	0.0148 (7)	0.0150 (7)	0.0175 (7)	−0.0016 (6)	0.0053 (6)	−0.0008 (6)
C13	0.0190 (7)	0.0155 (8)	0.0178 (7)	−0.0014 (6)	0.0045 (6)	−0.0009 (6)
C14	0.0219 (8)	0.0143 (8)	0.0219 (8)	−0.0007 (6)	0.0065 (6)	0.0017 (6)
C15	0.0209 (8)	0.0204 (8)	0.0192 (8)	−0.0008 (6)	0.0048 (6)	0.0052 (6)
C16	0.0212 (8)	0.0229 (9)	0.0161 (8)	−0.0041 (7)	0.0039 (6)	−0.0001 (6)
C17	0.0174 (7)	0.0157 (8)	0.0192 (8)	−0.0026 (6)	0.0062 (6)	−0.0026 (6)
C18	0.0176 (8)	0.0169 (8)	0.0240 (8)	−0.0010 (6)	0.0061 (6)	−0.0036 (6)
C19	0.0170 (8)	0.0175 (8)	0.0223 (8)	−0.0001 (6)	0.0030 (6)	−0.0033 (6)
C20	0.0249 (9)	0.0159 (8)	0.0405 (11)	0.0000 (7)	0.0105 (8)	0.0007 (7)
C21	0.0220 (9)	0.0230 (9)	0.0342 (10)	−0.0060 (7)	0.0083 (7)	0.0035 (7)
C22	0.0178 (8)	0.0292 (10)	0.0289 (9)	0.0042 (7)	0.0056 (7)	−0.0035 (7)
C23	0.0211 (8)	0.0210 (9)	0.0226 (8)	0.0046 (7)	0.0004 (7)	−0.0024 (6)
C24	0.0191 (8)	0.0170 (8)	0.0171 (8)	−0.0004 (6)	0.0006 (6)	−0.0015 (6)

Br1—C24	1.8992 (17)	C10—C11	1.388 (3)
O1—C1	1.3555 (19)	C10—H10	0.9500
O1—C5	1.4017 (19)	C11—H11	0.9500
O2—C17	1.378 (2)	C12—C17	1.391 (2)
O2—C18	1.382 (2)	C12—C13	1.402 (2)
O3—C18	1.210 (2)	C13—C14	1.382 (2)
C1—C2	1.350 (2)	C13—H13	0.9500
C1—C12	1.443 (2)	C14—C15	1.399 (2)
C2—C18	1.452 (2)	C14—H14	0.9500
C2—C3	1.508 (2)	C15—C16	1.385 (2)
C3—C4	1.506 (2)	C15—H15	0.9500
C3—C19	1.531 (2)	C16—C17	1.392 (2)
C3—H3	1.0000	C16—H16	0.9500
C4—C5	1.327 (2)	C19—C20	1.396 (2)
C4—H4	0.9500	C19—C24	1.396 (2)
C5—C6	1.475 (2)	C20—C21	1.363 (3)
C6—C11	1.389 (3)	C20—H20	0.9500
C6—C7	1.391 (3)	C21—C22	1.400 (3)
C7—C8	1.392 (3)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.388 (3)
C8—C9	1.375 (3)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.390 (2)
C9—C10	1.369 (3)	C23—H23	0.9500
C9—H9	0.9500
C1—O1—C5	117.97 (13)	C17—C12—C1	117.11 (14)
C17—O2—C18	121.86 (13)	C13—C12—C1	124.00 (15)
C2—C1—O1	123.61 (15)	C14—C13—C12	120.12 (15)
C2—C1—C12	122.46 (15)	C14—C13—H13	119.9
O1—C1—C12	113.94 (13)	C12—C13—H13	119.9
C1—C2—C18	118.84 (15)	C13—C14—C15	119.80 (15)
C1—C2—C3	122.47 (15)	C13—C14—H14	120.1
C18—C2—C3	118.63 (14)	C15—C14—H14	120.1
C4—C3—C2	108.83 (13)	C16—C15—C14	121.13 (16)
C4—C3—C19	109.64 (14)	C16—C15—H15	119.4
C2—C3—C19	112.78 (14)	C14—C15—H15	119.4
C4—C3—H3	108.5	C15—C16—C17	118.28 (16)
C2—C3—H3	108.5	C15—C16—H16	120.9
C19—C3—H3	108.5	C17—C16—H16	120.9
C5—C4—C3	124.17 (16)	O2—C17—C12	121.13 (15)
C5—C4—H4	117.9	O2—C17—C16	117.06 (15)
C3—C4—H4	117.9	C12—C17—C16	121.79 (15)
C4—C5—O1	121.81 (15)	O3—C18—O2	116.61 (15)
C4—C5—C6	128.24 (16)	O3—C18—C2	124.89 (17)
O1—C5—C6	109.95 (14)	O2—C18—C2	118.49 (14)
C11—C6—C7	118.06 (17)	C20—C19—C24	117.06 (16)
C11—C6—C5	120.72 (16)	C20—C19—C3	119.52 (15)
C7—C6—C5	121.19 (16)	C24—C19—C3	123.37 (15)
C6—C7—C8	120.51 (19)	C21—C20—C19	122.03 (17)
C6—C7—H7	119.7	C21—C20—H20	119.0
C8—C7—H7	119.7	C19—C20—H20	119.0
C9—C8—C7	120.7 (2)	C20—C21—C22	120.34 (17)
C9—C8—H8	119.6	C20—C21—H21	119.8
C7—C8—H8	119.6	C22—C21—H21	119.8
C10—C9—C8	119.04 (18)	C23—C22—C21	119.17 (17)
C10—C9—H9	120.5	C23—C22—H22	120.4
C8—C9—H9	120.5	C21—C22—H22	120.4
C9—C10—C11	120.99 (19)	C22—C23—C24	119.55 (17)
C9—C10—H10	119.5	C22—C23—H23	120.2
C11—C10—H10	119.5	C24—C23—H23	120.2
C10—C11—C6	120.65 (18)	C23—C24—C19	121.83 (16)
C10—C11—H11	119.7	C23—C24—Br1	117.66 (13)
C6—C11—H11	119.7	C19—C24—Br1	120.51 (13)
C17—C12—C13	118.89 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg4i	1.00	2.80	3.4956 (18)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg4i	1.00	2.80	3.4956 (18)	127

Symmetry code: (i) .