(E)-3-(Biphenyl-4-yl)-1-(3-bromo­phen­yl)prop-2-en-1-one

Dutkiewicz, G.; Chidan Kumar, C.S.; Yathirajan, H.S.; Narayana, B.; Kubicki, M.

doi:10.1107/S1600536809043384

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2856-o2857

https://doi.org/10.1107/S1600536809043384

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(E)-3-(Biphenyl-4-yl)-1-(3-bromophenyl)prop-2-en-1-one

Grzegorz Dutkiewicz,^a C. S. Chidan Kumar,^b H. S. Yathirajan,^b B. Narayana ^c and Maciej Kubicki ^a ^*

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 15 October 2009; accepted 21 October 2009; online 28 October 2009)

In the title compound, C₂₁H₁₅BrO, there are two planar rings connected through a conjugated double bond. As it crystallizes in a non-centrosymmetric space group it can be regarded as a good candidate for non-linear optical applications. The molecule adopts an E configuration and the C—C=C—C torsion angle is 177.1 (4)°. The overall conformation of the compound may be described by the values of dihedral angles between the approximately planar parts. The terminal rings are twisted by an angle of 51.52 (9)°, while the biphenyl part is almost planar, the dihedral angle between the planes of the rings being 4.44 (17)°. The unit cell has one long dimension, above 35 Å, characteristic also of a majority of related compounds. The molecules pack head-to-tail along this direction. C—H⋯π interactions are observed in the crystal structure.

Related literature

For applications of chalcones, see: Cho et al. (1996 ); Dinkova-Kostova et al., (1998 ); Fichou et al. (1988 ); Liu et al. (2003 ); Nielson et al. (1998 ); Rajas et al. (2002 ); Sarojini et al. (2006 ). For related structures, see: Fischer et al. (2007a ,b ,c ); Moorthi et al. (2007 ); Sarojini et al. (2007 ).

Experimental

Crystal data

C₂₁H₁₅BrO
M_r = 363.24
Orthorhombic, P c a 2₁
a = 6.092 (1) Å
b = 7.295 (1) Å
c = 36.619 (2) Å
V = 1627.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.53 mm⁻¹
T = 295 K
0.4 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis Pro. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.632, T_max = 1.000
5236 measured reflections
2766 independent reflections
2209 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.085
S = 1.05
2766 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.45 e Å⁻³
Absolute structure: Flack (1983 ), 1133 Friedel pairs
Flack parameter: 0.059 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1ⁱ	0.93	2.85	3.583 (5)	137
C6—H6⋯Cg1ⁱⁱ	0.93	2.78	3.516 (5)	137
C9—H9⋯Cg2ⁱ	0.93	2.87	3.544 (5)	131
C12—H12⋯Cg2ⁱⁱ	0.93	2.97	3.655 (5)	131
C21—H21⋯Cg3ⁱⁱⁱ	0.93	2.83	3.505 (5)	131
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+2, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+1, z]$ ; (iii) $[x-{\script{1\over 2}}, -y+2, z]$ . Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7–C12 and C17–C22 rings, respectively.

Data collection: CrysAlis Pro (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis Pro. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809043384/nk2009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043384/nk2009Isup2.hkl

checkCIF report

Comment top

For such a structurally simple group of compounds, chalcones have displayed an impressive array of biological activities, among which antimalarial (Liu et al., 2003), antiprotozoal (Nielson et al., 1998), nitric oxide inhibition (Rajas et al., 2002) and anticancer (Dinkova-Kostova et al., 1998) activities have been cited in the literature. Also, among organic compounds reported for non-linear optical (NLO) properties, chalcone derivatives are notable materials for their excellent blue-light transmittance and good crystallizability. They provide the necessary configuration to show NLO properties, with two planar rings connected through a conjugated double bond (e.g., Sarojini et al., 2006). Substitution on either of the benzene rings greatly influences the non-centrosymmetric crystal packing. It is speculated that, in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of non-centrosymmetric crystals (Fichou et al., 1988). The molecular hyperpolarizability is strongly influenced, not only by the electronic effect, but also by the steric effect of the substituent (Cho et al., 1996). Prompted by this, and in a continuation of our quest to synthesize new materials which can find use in the photonics industry, we have synthesized new chalcones and studied their SHG (second harmonic generation) efficiency.

(2E)-3-(biphenyl-4-yl)-1-(3-bromophenyl)prop-2-en-1-one (I) crystallizes in the non-centrosymmetric space group Pca2₁, which makes NLO activity possible. The overall conformation of the molecule can be described by the dihedral angles between the planar fragments: two rings of biphenyl system (A and B, cf. Fig. 1), the enone fragment (C) and the (bromo)phenyl ring (D). All these fragments are in a good approximation planar (maximum deviation from the least-squares plane is 0.018 (4)Å for the enone fragment). The biphenyl rings are almost coplanar, the dihedral angle between them is 4.44 (17)°; the enone fragment is significantly inclined with respect to both neighbouring rings, B/C angle is 30.74 (11)° and C/D - 16.34 (12)°.

The conformation for the ketone system is s–cis, as evidenced by the torsion angle O16—C15— C14—C13 of -21.7 (6)°. In general, the conformation of the molecule (I) is similar to the related compounds (e.g., Fischer et al., 2007a, b, c, Moorthi et al., 2007).

The unit cell of (I) has a long c axis of 36.619 (2) Å, and the molecules pack head-to-tail along this direction (Fig. 2). Such a long unit-cell parameter is observed in a number of similar compounds, even though they crystallize in different space groups and even in different crystal classes. For instance, 4-bromo (Fischer et al., 2007b), 4-chloro (Fischer et al., 2007a) and 4-methoxyphenyl (Fischer et al., 2007c) analogues crystallize all in the Cc space groups with the long parameter (ca. 36 Å) along c-direction, 4-fluoro derivative (Sarojini et al., 2007) - in P2₁ space group (Z' = 2) with the long b direction etc. It might be also noted, that other unit-cell parameters in all these structures are also similar to those observed in (I), and the comparison of the packing modes shows a significant degree of isostructurality. This suggests that the same interactions are responsible for the crystal packing in these structures: these can be some relatively short and linear C—H···π contacts, and van der Waals interactions.

Related literature top

For applications of chalcones, see: Cho et al. (1996); Dinkova-Kostova et al., (1998); Fichou et al. (1988); Liu et al. (2003); Nielson et al. (1998); Rajas et al. (2002); Sarojini et al. (2006). For related structures, see: Fischer et al. (2007a,b,c); Moorthi et al. (2007); Sarojini et al. (2007). Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7–C12 and C17–C22 rings, respectively.

Experimental top

5 ml 40% KOH solution was added to a thoroughly stirred solution of 3-bromoacetophenone (1.0 g, 5 m mol) and 4-biphenylcarboxaldehyde (1.0 g, 5.4 m mol) in 15 ml of methanol. The mixture was stirred overnight and filtered. The product formed was crystallized in methanol. X-ray quality crystals were grown from slow evaporation of ethyl acetate solution (m.p.: 378 – 380 K).

Structure description top

For applications of chalcones, see: Cho et al. (1996); Dinkova-Kostova et al., (1998); Fichou et al. (1988); Liu et al. (2003); Nielson et al. (1998); Rajas et al. (2002); Sarojini et al. (2006). For related structures, see: Fischer et al. (2007a,b,c); Moorthi et al. (2007); Sarojini et al. (2007). Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C7–C12 and C17–C22 rings, respectively.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic ellipsoid representation of the compound I together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii.
	Fig. 2. The crystal packing as seen along [100] direction.

(E)-3-(Biphenyl-4-yl)-1-(3-bromophenyl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₅BrO	F(000) = 736
M_r = 363.24	D_x = 1.483 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2900 reflections
a = 6.092 (1) Å	θ = 2.2–26.8°
b = 7.295 (1) Å	µ = 2.53 mm⁻¹
c = 36.619 (2) Å	T = 295 K
V = 1627.4 (4) Å³	Prism, colourless
Z = 4	0.4 × 0.2 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer	2766 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2209 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 8.1929 pixels mm^-1	θ_max = 26.9°, θ_min = 2.2°
ω scans	h = −5→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	k = −5→9
T_min = 0.632, T_max = 1.000	l = −45→41
5236 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.050P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2766 reflections	Δρ_max = 0.25 e Å⁻³
208 parameters	Δρ_min = −0.45 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1133 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.059 (11)

Crystal data top

C₂₁H₁₅BrO	V = 1627.4 (4) Å³
M_r = 363.24	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 6.092 (1) Å	µ = 2.53 mm⁻¹
b = 7.295 (1) Å	T = 295 K
c = 36.619 (2) Å	0.4 × 0.2 × 0.2 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer	2766 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	2209 reflections with I > 2σ(I)
T_min = 0.632, T_max = 1.000	R_int = 0.022
5236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.085	Δρ_max = 0.25 e Å⁻³
S = 1.05	Δρ_min = −0.45 e Å⁻³
2766 reflections	Absolute structure: Flack (1983), 1133 Friedel pairs
208 parameters	Absolute structure parameter: 0.059 (11)
1 restraint

Special details top

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
C1	0.6509 (7)	0.7425 (7)	0.79823 (11)	0.0516 (11)
H1	0.5927	0.7379	0.7748	0.062*
C2	0.8449 (7)	0.8289 (5)	0.80447 (11)	0.0532 (10)
H2	0.9194	0.8847	0.7853	0.064*
C3	0.9320 (7)	0.8337 (5)	0.83967 (9)	0.0430 (9)
H3	1.0645	0.8938	0.8437	0.052*
C4	0.8253 (6)	0.7506 (5)	0.86911 (10)	0.0333 (7)
C5	0.6238 (6)	0.6661 (4)	0.86149 (11)	0.0407 (9)
H5	0.5454	0.6120	0.8804	0.049*
C6	0.5403 (7)	0.6612 (5)	0.82712 (12)	0.0504 (10)
H6	0.4072	0.6026	0.8229	0.061*
C7	0.9218 (6)	0.7517 (5)	0.90615 (9)	0.0302 (7)
C8	1.1289 (5)	0.8263 (5)	0.91272 (10)	0.0376 (8)
H8	1.2081	0.8759	0.8934	0.045*
C9	1.2194 (6)	0.8281 (5)	0.94747 (11)	0.0390 (8)
H9	1.3586	0.8776	0.9508	0.047*
C10	1.1075 (6)	0.7580 (5)	0.97729 (10)	0.0364 (8)
C11	0.9024 (6)	0.6836 (5)	0.97075 (10)	0.0424 (9)
H11	0.8234	0.6346	0.9902	0.051*
C12	0.8120 (6)	0.6801 (5)	0.93638 (11)	0.0398 (8)
H12	0.6738	0.6284	0.9332	0.048*
C13	1.2154 (6)	0.7575 (6)	1.01312 (11)	0.0449 (9)
H13	1.3613	0.7952	1.0136	0.054*
C14	1.1287 (7)	0.7096 (6)	1.04483 (11)	0.0494 (10)
H14	0.9815	0.6761	1.0461	0.059*
C15	1.2648 (7)	0.7089 (5)	1.07855 (11)	0.0476 (9)
O16	1.4619 (5)	0.6988 (4)	1.07694 (8)	0.0696 (9)
C17	1.1481 (6)	0.7302 (5)	1.11410 (10)	0.0412 (8)
C18	1.2662 (6)	0.6895 (4)	1.14615 (10)	0.0380 (8)
H18	1.4069	0.6405	1.1447	0.046*
C19	1.1730 (6)	0.7225 (5)	1.17930 (11)	0.0435 (8)
C20	0.9649 (8)	0.7894 (5)	1.18260 (12)	0.0515 (10)
H20	0.9028	0.8092	1.2055	0.062*
C21	0.8486 (6)	0.8273 (5)	1.15093 (14)	0.0487 (11)
H21	0.7074	0.8751	1.1526	0.058*
C22	0.9371 (7)	0.7956 (5)	1.11731 (11)	0.0477 (9)
H22	0.8545	0.8183	1.0964	0.057*
Br23	1.33920 (7)	0.67882 (6)	1.222156 (16)	0.06635 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.071 (3)	0.044 (2)	0.040 (2)	0.008 (2)	−0.014 (2)	−0.0040 (19)
C2	0.071 (3)	0.054 (2)	0.035 (2)	−0.006 (2)	0.0032 (17)	0.0005 (16)
C3	0.042 (2)	0.054 (2)	0.0327 (18)	−0.0073 (18)	0.0040 (14)	−0.0016 (15)
C4	0.038 (2)	0.0254 (16)	0.0363 (17)	0.0042 (15)	0.0029 (14)	−0.0008 (13)
C5	0.044 (2)	0.0343 (19)	0.044 (2)	−0.0048 (15)	−0.0018 (15)	0.0043 (15)
C6	0.057 (3)	0.045 (2)	0.049 (2)	−0.0094 (18)	−0.0123 (19)	0.0004 (18)
C7	0.0334 (19)	0.0240 (15)	0.0332 (16)	0.0007 (14)	0.0039 (13)	0.0004 (12)
C8	0.036 (2)	0.040 (2)	0.0362 (18)	−0.0046 (15)	0.0024 (13)	0.0039 (14)
C9	0.0300 (19)	0.041 (2)	0.046 (2)	−0.0043 (15)	−0.0044 (15)	−0.0022 (15)
C10	0.037 (2)	0.0369 (18)	0.0354 (18)	−0.0008 (15)	−0.0013 (13)	−0.0026 (15)
C11	0.043 (2)	0.048 (2)	0.036 (2)	−0.0089 (17)	0.0034 (15)	0.0064 (16)
C12	0.031 (2)	0.048 (2)	0.0408 (18)	−0.0061 (17)	−0.0008 (13)	−0.0014 (15)
C13	0.050 (2)	0.042 (2)	0.043 (2)	0.0038 (18)	−0.0044 (18)	−0.0012 (17)
C14	0.043 (2)	0.066 (3)	0.038 (2)	−0.0047 (19)	−0.0095 (16)	−0.0006 (18)
C15	0.046 (2)	0.056 (2)	0.040 (2)	−0.0019 (19)	−0.0052 (17)	−0.0007 (17)
O16	0.0414 (18)	0.118 (3)	0.0490 (17)	0.0122 (17)	−0.0012 (13)	−0.0013 (16)
C17	0.037 (2)	0.046 (2)	0.0412 (19)	−0.0037 (17)	−0.0081 (14)	−0.0013 (16)
C18	0.0331 (19)	0.0402 (19)	0.0406 (19)	−0.0016 (15)	−0.0073 (14)	−0.0010 (15)
C19	0.041 (2)	0.048 (2)	0.042 (2)	−0.0057 (18)	−0.0078 (15)	−0.0001 (16)
C20	0.051 (3)	0.058 (2)	0.045 (2)	−0.001 (2)	0.0027 (17)	−0.0004 (18)
C21	0.035 (2)	0.051 (2)	0.060 (3)	−0.0022 (18)	−0.0076 (17)	0.000 (2)
C22	0.044 (2)	0.047 (2)	0.052 (2)	−0.0032 (18)	−0.0090 (18)	0.0020 (16)
Br23	0.0653 (3)	0.0941 (3)	0.03960 (19)	0.0043 (2)	−0.0142 (2)	0.0021 (3)

Geometric parameters (Å, º) top

C1—C2	1.358 (6)	C11—C12	1.374 (5)
C1—C6	1.387 (6)	C11—H11	0.9300
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.394 (5)	C13—C14	1.323 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.397 (5)	C14—C15	1.487 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.401 (5)	C15—O16	1.204 (5)
C4—C7	1.478 (5)	C15—C17	1.492 (6)
C5—C6	1.358 (5)	C17—C22	1.376 (6)
C5—H5	0.9300	C17—C18	1.408 (5)
C6—H6	0.9300	C18—C19	1.361 (5)
C7—C12	1.395 (5)	C18—H18	0.9300
C7—C8	1.395 (5)	C19—C20	1.364 (6)
C8—C9	1.387 (5)	C19—Br23	1.894 (4)
C8—H8	0.9300	C20—C21	1.387 (6)
C9—C10	1.385 (5)	C20—H20	0.9300
C9—H9	0.9300	C21—C22	1.364 (6)
C10—C11	1.383 (5)	C21—H21	0.9300
C10—C13	1.468 (5)	C22—H22	0.9300

C2—C1—C6	119.5 (4)	C10—C11—H11	119.1
C2—C1—H1	120.3	C11—C12—C7	121.9 (3)
C6—C1—H1	120.2	C11—C12—H12	119.1
C1—C2—C3	119.9 (4)	C7—C12—H12	119.1
C1—C2—H2	120.0	C14—C13—C10	127.3 (4)
C3—C2—H2	120.1	C14—C13—H13	116.3
C2—C3—C4	121.7 (4)	C10—C13—H13	116.3
C2—C3—H3	119.2	C13—C14—C15	120.4 (4)
C4—C3—H3	119.2	C13—C14—H14	119.8
C3—C4—C5	116.4 (3)	C15—C14—H14	119.8
C3—C4—C7	121.4 (3)	O16—C15—C14	121.0 (4)
C5—C4—C7	122.2 (3)	O16—C15—C17	121.6 (3)
C6—C5—C4	121.6 (4)	C14—C15—C17	117.3 (4)
C6—C5—H5	119.2	C22—C17—C18	118.6 (4)
C4—C5—H5	119.2	C22—C17—C15	123.8 (3)
C5—C6—C1	120.9 (4)	C18—C17—C15	117.5 (3)
C5—C6—H6	119.5	C19—C18—C17	119.5 (4)
C1—C6—H6	119.5	C19—C18—H18	120.2
C12—C7—C8	116.3 (3)	C17—C18—H18	120.2
C12—C7—C4	122.4 (3)	C18—C19—C20	122.0 (4)
C8—C7—C4	121.3 (3)	C18—C19—Br23	119.1 (3)
C9—C8—C7	121.4 (3)	C20—C19—Br23	118.9 (3)
C9—C8—H8	119.3	C19—C20—C21	118.2 (4)
C7—C8—H8	119.3	C19—C20—H20	120.9
C10—C9—C8	121.6 (3)	C21—C20—H20	120.9
C10—C9—H9	119.2	C22—C21—C20	121.2 (4)
C8—C9—H9	119.2	C22—C21—H21	119.4
C11—C10—C9	116.9 (3)	C20—C21—H21	119.4
C11—C10—C13	124.0 (3)	C21—C22—C17	120.4 (4)
C9—C10—C13	119.0 (3)	C21—C22—H22	119.8
C12—C11—C10	121.9 (3)	C17—C22—H22	119.8
C12—C11—H11	119.1

C6—C1—C2—C3	0.6 (6)	C4—C7—C12—C11	−179.3 (3)
C1—C2—C3—C4	0.3 (6)	C11—C10—C13—C14	−9.0 (7)
C2—C3—C4—C5	−1.4 (5)	C9—C10—C13—C14	174.4 (4)
C2—C3—C4—C7	178.2 (4)	C10—C13—C14—C15	177.1 (4)
C3—C4—C5—C6	1.7 (5)	C13—C14—C15—O16	−21.7 (6)
C7—C4—C5—C6	−178.0 (3)	C13—C14—C15—C17	155.4 (4)
C4—C5—C6—C1	−0.9 (6)	O16—C15—C17—C22	160.0 (4)
C2—C1—C6—C5	−0.3 (6)	C14—C15—C17—C22	−17.1 (5)
C3—C4—C7—C12	175.8 (3)	O16—C15—C17—C18	−16.7 (6)
C5—C4—C7—C12	−4.6 (5)	C14—C15—C17—C18	166.3 (3)
C3—C4—C7—C8	−3.8 (5)	C22—C17—C18—C19	−2.6 (5)
C5—C4—C7—C8	175.8 (3)	C15—C17—C18—C19	174.2 (3)
C12—C7—C8—C9	0.1 (5)	C17—C18—C19—C20	1.9 (6)
C4—C7—C8—C9	179.7 (3)	C17—C18—C19—Br23	−176.8 (3)
C7—C8—C9—C10	−0.7 (5)	C18—C19—C20—C21	−1.1 (6)
C8—C9—C10—C11	0.9 (5)	Br23—C19—C20—C21	177.6 (3)
C8—C9—C10—C13	177.7 (4)	C19—C20—C21—C22	1.2 (6)
C9—C10—C11—C12	−0.5 (5)	C20—C21—C22—C17	−2.0 (6)
C13—C10—C11—C12	−177.1 (4)	C18—C17—C22—C21	2.7 (6)
C10—C11—C12—C7	−0.2 (6)	C15—C17—C22—C21	−173.9 (3)
C8—C7—C12—C11	0.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.85	3.583 (5)	137
C6—H6···Cg1ⁱⁱ	0.93	2.78	3.516 (5)	137
C9—H9···Cg2ⁱ	0.93	2.87	3.544 (5)	131
C12—H12···Cg2ⁱⁱ	0.93	2.97	3.655 (5)	131
C21—H21···Cg3ⁱⁱⁱ	0.93	2.83	3.505 (5)	131

Symmetry codes: (i) x+1/2, −y+2, z; (ii) x−1/2, −y+1, z; (iii) x−1/2, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅BrO
M_r	363.24
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	295
a, b, c (Å)	6.092 (1), 7.295 (1), 36.619 (2)
V (Å³)	1627.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.53
Crystal size (mm)	0.4 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2 (large Be window)
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)
T_min, T_max	0.632, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5236, 2766, 2209
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.637

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.085, 1.05
No. of reflections	2766
No. of parameters	208
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.45
Absolute structure	Flack (1983), 1133 Friedel pairs
Absolute structure parameter	0.059 (11)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Stereochemical Workstation Operation Manual (Siemens, 1989).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1ⁱ	0.93	2.85	3.583 (5)	137.0
C6—H6···Cg1ⁱⁱ	0.93	2.78	3.516 (5)	136.5
C9—H9···Cg2ⁱ	0.93	2.87	3.544 (5)	130.7
C12—H12···Cg2ⁱⁱ	0.93	2.97	3.655 (5)	131.4
C21—H21···Cg3ⁱⁱⁱ	0.93	2.83	3.505 (5)	130.7

Symmetry codes: (i) x+1/2, −y+2, z; (ii) x−1/2, −y+1, z; (iii) x−1/2, −y+2, z.

Acknowledgements

CSC thanks the University of Mysore for research facilities.

References

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