4-(2-Bromo­phen­yl)-2-phenyl­pyrano[3,2-c]chromen-5(4H)-one

Gohain, M.; Loganathan, N.; Bezuidenhoudt, B.C.B.; Roodt, A.

doi:10.1107/S1600536812044510

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3279-o3280

doi:10.1107/S1600536812044510

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4-(2-Bromophenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one

Mukut Gohain,^a Nagarajan Loganathan,^a ^* Barend C. B. Bezuidenhoudt ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
^*Correspondence e-mail: nagagold@gmail.com

(Received 5 October 2012; accepted 26 October 2012; online 3 November 2012)

In the title compound, C₂₄H₁₅BrO₃, the pyranochromenone ring is essentially planar, while the 2-bromophenyl 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 interatomic 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_r = 431.27
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.068
S = 1.05
4464 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) -x+1, -y+2, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044510/bv2211sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812044510/bv2211Isup3.cml

checkCIF report

Comment top

Compound 1 is a derivative of a well known phytochemical called coumarin. The derivatives of coumarins are valued for their interesting medicinal applications (Murray et al., 1982; Heide et al., 2009 & Soine et al., 1964). For example, some of them are inhibitors of HIV-1 reverse transcriptase (Patil et al., 1993), while others are being used as anti-bacterial (Verotta et al., 2004), anti-biotic (Hinman et al., 1956) and anti-neoplastic (Magolan et al., 2012) agents. Many authors have synthesized coumarin derivatives using their own approaches (Naveen et al., 2007; Shaabani et al., 2008 & Sarma et al., 2010) and we adapted the synthetic procedure by He et al., 2010. There are also quite a few structures published that are related to compound 1 (Shi et al., 2004; Shi et al., 2005; He et al., 2010 & Lakshmi et al.,2006).

Recently He et al., 2010, synthesized various functionalized pyranochromenones and reported the crystal structure of the 2,4-diphenyl pyrano(3,2 - c)chromen-5(4H)-one (2). Structurally, both compounds 1 and 2 are quite similar. We adapted their synthetic method for the preparation of 1. Our close examination of the crystal structure 1 (Fig. 1) reveals that the bonds C2—C3 (1.508 (2) Å and C3—C4 (1.506 (2) Å are essentially single bonds. The mean plane analysis of 1 shows the pyranochromen-5(4H)-one ring is almost planar. The deviation observed is maximum for the C4 [(0.1166 (17) Å] and C5 [(0.1024 (14) Å] atoms located next to O1 and primary C3 of the pyran ring respectively. The dihedral angle between the chromene (atoms C12 to C17, O2, C18, C1 and C2) and pyrane (C1 to C5 and O1) of pyranochromen-5(4H)-one ring is 5.39 (5) °. The phenyl group (atoms C6 to C11) attached to C5 is slightly tilted from the parent plane (dihedral angle is 17.50 (8) ° and the torsion angle of O1—C5—C6—C7 is 157.68 (1) °. The 2-bromophenyl group (C19 to C24 and Br1) connected to C3 is almost perpendicular to the pyranochromen-5(4H)-one ring [dihedral angle is 85.58 (6)° and torsion angles of C4—C3—C19—C20 is 81.41 (8) and C4—C3—C19—C24 is 95.90 (1)°].

Several edge-to-face intermolecular C—H ··· π interactions are observed in compound 1 (Fig. 2) and the atomic parameters [distance and angles] are as follows.

a) phenyl ring of the chromenone with C3—H3 [2.804 (1) Å; 146.75 (4)°] and C4—H4 [3.812 (4) Å; 92.71 (4)°] of pyran ring.

b) phenyl ring of the chromenone with C9—H9 [3.798 (4) Å; 84.12 (2)°] and C10—H10 [3.238 (2) Å; 95.65 (3)°] of 2-phenyl group.

c) 2-bromophenyl ring with C9—H9 [3.076 (2) Å; 141.50 (3)°] and C8—H8 [3.652 (5) Å; (115.99 (2)°] of 2-phenyl group.

d) 2-phenyl ring with C23—H23 [3.301 (8) Å; (146.75 (8)°] of 2-bromophenyl group and [C7—H73.639 (4) Å; (128.73 (3)°] of 2-phenyl group.

Strong C—H ··· Br intramolecular interaction is also observed [C3—H3 ··· Br1 2.668 (7) Å; 113.66 (9)°]. The unit cell packing diagram shows a zigzag arrangement of atoms running along the b axis (Fig. 3). There is also a short interatomic contact found between Br1 and O3 (3.016 (1)Å).

Related literature top

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 top

The synthesis is adapted from the procedure previously published (He et al. 2010). A mixture of 4-hydroxycoumarin (0.3 mmol) and 3-(2-bromophenyl)-1-phenylprop-2-en-1-one (0.25 mmol) and 4 Å molecular sieves (0.25 g) were taken in 5 ml of dichloromethane solvent. 2, 3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (0.5 mmol) was added in portions during 15 min and the reaction mixture were allowed to stir for the 20–30 min. It was then filtered through a Celite plug and purified by column chromatography on silica gel with petroleum ether and ethyl acetate (10:1) as the eluent. The solution was evaporated under vacuo and the pale yellow solid obtained was dissolved in hot acetonitrile. Upon slow evaporation, colourless crystals suitable for X-ray diffraction were obtained. m.p. 238–239°C; Yield. 80%. 1H NMR (600 MHz, CDCl3) δ 8.05 (d, J = 10.3 Hz, 1H), 7.72 (d, J = 7.3 Hz, 2H), 7.68 – 7.53 (m, 2H), 7.49 – 7.39 (m, 5H), 7.32 – 7.07 (m, 2H), 5.91 (d, J = 4.1 Hz, 1H), 5.25 (d, J = 4.0 Hz, 1H). 13 C NMR (150 MHz, CDCl3) δ 161.2(C), 157.3(C), 153.1(C), 146.9(C), 142.5(C), 133.3(CH), 132.6(C), 132.4(CH), 129.7(CH), 129.4(CH), 128.7(2xCH), 128.6(CH), 128.2(CH), 124.8(2xCH), 124.4(CH), 123.4(C), 122.9(CH), 117.1(CH), 114.4(C), 102.4(CH), 102.3(C), 36.5(CH).

Computing details top

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

Figures top

	Fig. 1. DIAMOND 3.2i picture of the title compound 1 (ellipsoid model with 50% probability).
	Fig. 2. DIAMOND 3.2i picture of 1, showing the intermolecular C—H ••• π interactions. symmetry codes are 2 - x, 0.5 + y, 0.5 - z; 2 - x, -y, 1 - z; x, y, z; 1 - x, -y, -z.
	Fig. 3. Unit cell packing of the title compound 1 along a-c place (DIAMOND 3.2i representation).

4-(2-Bromophenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one top

Crystal data top

C₂₄H₁₅BrO₃	F(000) = 872
M_r = 431.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0271P)² + 1.4892P] where P = (F_o² + 2F_c²)/3
4464 reflections	(Δ/σ)_max = 0.003
253 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₂₄H₁₅BrO₃	V = 1793.53 (7) Å³
M_r = 431.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.5959 (2) Å	µ = 2.32 mm⁻¹
b = 17.7890 (4) Å	T = 100 K
c = 8.7610 (2) Å	0.52 × 0.40 × 0.23 mm
β = 97.060 (1)°

Data collection top

Bruker X8 APEXII KappaCCD diffractometer	4464 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4019 reflections with I > 2σ(I)
T_min = 0.380, T_max = 0.618	R_int = 0.045
41256 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.068	H-atom parameters constrained
S = 1.05	Δρ_max = 0.51 e Å⁻³
4464 reflections	Δρ_min = −0.34 e Å⁻³
253 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅BrO₃
M_r	431.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.5959 (2), 17.7890 (4), 8.7610 (2)
β (°)	97.060 (1)
V (Å³)	1793.53 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.32
Crystal size (mm)	0.52 × 0.40 × 0.23

Data collection
Diffractometer	Bruker X8 APEXII KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.380, 0.618
No. of measured, independent and observed [I > 2σ(I)] reflections	41256, 4464, 4019
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.068, 1.05
No. of reflections	4464
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.34

Computer programs: APEX2 (Bruker, 2008), SAINT-Plus (Bruker, 2008), SHELXTL (Sheldrick, 2008) and WinGX (Farrugia,1999), SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z.

Acknowledgements

The University of the Free State and Sasol Ltd are gratefully acknowledged for financial support.

References

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Volume 68| Part 12| December 2012| Pages o3279-o3280

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