(2E)-3-(3-Bromo-4-meth­oxy­phen­yl)-1-(pyridin-2-yl)prop-2-en-1-one

Jasinski, J.P.; Butcher, R.J.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811000353

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o352-o353

doi:10.1107/S1600536811000353

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(2E)-3-(3-Bromo-4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b S. Samshuddin,^c B. Narayana ^c and H. S. Yathirajan ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 31 December 2010; accepted 5 January 2011; online 12 January 2011)

The mean planes of the benzene and pyridine rings in the title compound, C₁₅H₁₂BrNO₂, are nearly coplanar, subtending an angle of 2.8 (8)°. The prop-2-en-1-one group is also in the plane of these rings with an N—C—C—O torsion angle of 179.6 (3)°. A weak C—H⋯Br intermolecular interaction contributes to the crystal packing, creating a chain-like structure along the a axis.

Related literature

For the pharmacological activity of chalcones, see: Dhar (1981 ); Dimmock et al. (1999 ); Satyanarayana et al. (2004 ). For their ability to block voltage-dependent potassium channels, see: Yarishkin et al. (2008 ). For their applications as organic non-linear optical materials due to their SHG conversion efficiency, see: Sarojini et al. (2006 ) and excellent blue light transmittance and good crystallization ability, see: Goto et al. (1991 ); Indira et al. (2002 ); Uchida et al. (1998 ). For the use of chalcones in the synthesis of various biodynamic heterocyclic compounds such as cyclohexenone and pyrazoline derivatives, see: Ashalatha et al. (2009 ); Sreevidya et al. (2010 ); Samshuddin et al. (2010 ); Fun et al. (2010a ,b ); Jasinski et al. (2010a ,b ). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999 ). For related structures, see: Bibila Mayaya Bisseyou et al. (2007 ); Liu et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₂BrNO₂
M_r = 318.17
Monoclinic, C 2/c
a = 26.3402 (13) Å
b = 3.8906 (2) Å
c = 27.5826 (17) Å
β = 113.892 (5)°
V = 2584.4 (2) Å³
Z = 8
Cu Kα radiation
μ = 4.31 mm⁻¹
T = 123 K
0.49 × 0.21 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.535, T_max = 1.000
3978 measured reflections
2556 independent reflections
2431 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.115
S = 1.08
2556 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Br1ⁱ	0.95	3.04	3.870 (3)	146
Symmetry code: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000353/ng5098sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000353/ng5098Isup2.hkl

checkCIF report

Comment top

Chalcones constitute an important family of substances belonging to flavonoids, a large group of natural and synthetic products with interesting physicochemical properties, biological activity and structural characteristics. Chalcones are highly reactive substances of varied nature. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Among several organic compounds reported which have NLO properties, chalcone derivatives are a recognized material because of their excellent blue light transmittance and good crystallization ability (Goto et al.,1991; Uchida et al.,1998; Indira et al., 2002). The basic skeleton of chalcones which possess α,β-unsaturated carbonyl group is useful as the starting material for the synthesis of various biodynamic heterocyclic compounds such as cyclohexenone derivatives and pyrazoline derivatives (Ashalatha et al., 2009; Sreevidya et al., 2010; Samshuddin et al., 2010; Fun et al., 2010a,b; Jasinski et al., 2010a,b). The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using these compounds or chalcone rich plant extracts as drugs or food preservatives (Di Carlo et al., 1999). The crystal structures of some chalcones derived from acetyl pyridine viz., (Z)-3-(2,6-dichlorophenyl)-1-(pyridin-3-yl)-2- (1H-1,2,4-triazol-1-yl)prop-2-en-1-one (Liu et al., 2005), 3-(3-chlorophenyl)-1-(2-methylimidazo[1,2-a]pyridin-3-yl)prop-2-en-1-one (Bibila Mayaya Bisseyou et al., 2007) have been reported. In continuation of our studies on chalcones and their derivatives, the title compound (I) was prepared and its crystal structure is reported.

The mean planes of the benzene and pyridine rings in the title compound, C₁₅H₁₂BrNO₂, are nearly planar being separated by only 2.8 (8)° (Fig. 2). The prop-2-en-1-one group is also in the plane of these rings with a N1-C1-C6-O1 torsion angle of 179.6 (3)°. A weak C—H···Br intermolecular interaction (Table 1) contributes to crystal packing creating a 2-D network structure along [101].(Fig. 3).

Related literature top

For the pharmacological activity of chalcones, see: Dhar (1981); Dimmock et al. (1999); Satyanarayana et al. (2004). For their ability to block voltage-dependent potassium channels, see: Yarishkin et al. (2008). For their applications as organic non-linear optical materials due to their SHG conversion efficiency, see: Sarojini et al. (2006) and excellent blue light transmittance and good crystallization ability, see: Goto et al. (1991); Indira et al. (2002); Uchida et al. (1998). For the use of chalcones in the synthesis of various biodynamic heterocyclic compounds such as cyclohexenone and pyrazoline derivatives, see: Ashalatha et al. (2009); Sreevidya et al. (2010); Samshuddin et al. (2010); Fun et al. (2010a,b); Jasinski et al. (2010a,b). For the potential use of these compounds or chalcone-rich plant extracts as drugs or food preservatives, see: Di Carlo et al. (1999). For related structures, see: Bibila Mayaya Bisseyou et al. (2007); Liu et al. (2005).

Experimental top

To a mixture of 2-acetyl pyridine (1.21 g, 0.01 mol) and 3-bromo-4-methoxybenzaldehyde (2.15 g, 0.01 mol) in 30 ml e thanol, 10 ml of 10% sodium hydroxide solution was added and stirred at 5–10°C for 3 h (Fig. 1). The precipitate formed was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from acetonitrile by slow evaporation method and yield of the compound was 82%. (m.p. 428 K). Analytical data: Found (Cald): C %: 56.58(56.62); H%: 3.78 (3.80); N%: 4.37 (4.40).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. REaction scheme for C₁₅H₁₂BrNO₂.
	Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 3. Packing diagram of the title compound viewed down the b axis. Dashed lines indicate weak C—H···Br intermolecular hydrogen bond interactions creating a 2-D network structure along [101].

(2E)-3-(3-Bromo-4-methoxyphenyl)-1-(pyridin-2-yl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₂BrNO₂	F(000) = 1280
M_r = 318.17	D_x = 1.635 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 3510 reflections
a = 26.3402 (13) Å	θ = 4.7–74.0°
b = 3.8906 (2) Å	µ = 4.31 mm⁻¹
c = 27.5826 (17) Å	T = 123 K
β = 113.892 (5)°	Needle, colorless
V = 2584.4 (2) Å³	0.49 × 0.21 × 0.16 mm
Z = 8

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2556 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2431 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 6.0°
ω scans	h = −29→32
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −4→2
T_min = 0.535, T_max = 1.000	l = −34→33
3978 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0704P)² + 6.6225P] where P = (F_o² + 2F_c²)/3
2556 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₅H₁₂BrNO₂	V = 2584.4 (2) Å³
M_r = 318.17	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 26.3402 (13) Å	µ = 4.31 mm⁻¹
b = 3.8906 (2) Å	T = 123 K
c = 27.5826 (17) Å	0.49 × 0.21 × 0.16 mm
β = 113.892 (5)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2556 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2431 reflections with I > 2σ(I)
T_min = 0.535, T_max = 1.000	R_int = 0.014
3978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.08	Δρ_max = 0.85 e Å⁻³
2556 reflections	Δρ_min = −0.64 e Å⁻³
173 parameters

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
Br1	0.046034 (12)	0.06121 (9)	0.063358 (11)	0.03852 (15)
O1	0.36895 (11)	0.4707 (8)	0.17800 (10)	0.0507 (6)
O2	0.04309 (8)	0.3262 (7)	0.16281 (8)	0.0431 (5)
N1	0.30803 (11)	0.0395 (8)	0.05431 (11)	0.0410 (6)
C1	0.34866 (11)	0.1894 (9)	0.09571 (12)	0.0359 (6)
C2	0.40303 (12)	0.2175 (8)	0.10013 (13)	0.0382 (6)
H2A	0.4308	0.3251	0.1300	0.046*
C3	0.41559 (13)	0.0837 (9)	0.05953 (15)	0.0441 (8)
H3A	0.4523	0.0956	0.0614	0.053*
C4	0.37382 (15)	−0.0664 (9)	0.01663 (15)	0.0451 (8)
H4A	0.3812	−0.1569	−0.0119	0.054*
C5	0.32078 (15)	−0.0833 (9)	0.01567 (14)	0.0442 (8)
H5A	0.2922	−0.1875	−0.0140	0.053*
C6	0.33420 (13)	0.3330 (10)	0.13914 (12)	0.0420 (7)
C7	0.27542 (13)	0.3026 (9)	0.13151 (12)	0.0410 (7)
H7A	0.2503	0.1747	0.1023	0.049*
C8	0.25712 (14)	0.4531 (9)	0.16526 (13)	0.0404 (7)
H8A	0.2833	0.5857	0.1931	0.048*
C9	0.20072 (13)	0.4324 (9)	0.16324 (12)	0.0389 (7)
C10	0.15685 (12)	0.2790 (9)	0.12093 (11)	0.0359 (6)
H10A	0.1628	0.1909	0.0915	0.043*
C11	0.10531 (11)	0.2558 (7)	0.12193 (11)	0.0311 (6)
C12	0.09521 (12)	0.3743 (8)	0.16536 (11)	0.0335 (6)
C13	0.13844 (13)	0.5282 (9)	0.20707 (13)	0.0374 (7)
H13A	0.1327	0.6135	0.2367	0.045*
C14	0.19004 (14)	0.5571 (9)	0.20544 (13)	0.0395 (7)
H14A	0.2192	0.6660	0.2341	0.047*
C15	0.03317 (15)	0.4373 (11)	0.20775 (14)	0.0489 (9)
H15A	−0.0049	0.3784	0.2024	0.073*
H15B	0.0383	0.6868	0.2118	0.073*
H15C	0.0594	0.3227	0.2398	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0377 (2)	0.0436 (2)	0.0325 (2)	−0.00132 (12)	0.01247 (15)	−0.00231 (12)
O1	0.0427 (13)	0.0683 (16)	0.0394 (13)	−0.0095 (12)	0.0149 (11)	−0.0008 (11)
O2	0.0317 (10)	0.0681 (15)	0.0339 (10)	0.0021 (11)	0.0177 (8)	−0.0024 (11)
N1	0.0317 (13)	0.0494 (16)	0.0400 (14)	−0.0043 (11)	0.0124 (11)	0.0067 (12)
C1	0.0283 (13)	0.0413 (16)	0.0366 (14)	−0.0025 (12)	0.0116 (11)	0.0114 (13)
C2	0.0291 (13)	0.0392 (16)	0.0450 (16)	−0.0025 (12)	0.0136 (12)	0.0083 (13)
C3	0.0343 (16)	0.0416 (19)	0.060 (2)	0.0050 (13)	0.0231 (15)	0.0099 (15)
C4	0.0501 (19)	0.0388 (18)	0.0502 (19)	0.0078 (14)	0.0241 (16)	0.0077 (14)
C5	0.0418 (17)	0.0439 (19)	0.0430 (17)	−0.0038 (13)	0.0130 (14)	0.0025 (14)
C6	0.0341 (14)	0.0554 (19)	0.0385 (16)	0.0013 (14)	0.0168 (13)	0.0130 (15)
C7	0.0378 (15)	0.0466 (18)	0.0381 (15)	−0.0029 (14)	0.0149 (12)	−0.0003 (14)
C8	0.0409 (16)	0.0433 (18)	0.0346 (15)	−0.0030 (13)	0.0130 (13)	0.0018 (13)
C9	0.0340 (15)	0.0511 (19)	0.0322 (15)	0.0061 (13)	0.0141 (12)	0.0104 (13)
C10	0.0342 (13)	0.0466 (17)	0.0288 (13)	0.0082 (13)	0.0147 (11)	0.0069 (12)
C11	0.0319 (13)	0.0315 (14)	0.0289 (12)	0.0025 (11)	0.0113 (10)	0.0037 (11)
C12	0.0301 (13)	0.0391 (15)	0.0325 (14)	0.0051 (12)	0.0140 (11)	0.0040 (12)
C13	0.0385 (16)	0.0416 (16)	0.0326 (14)	0.0069 (13)	0.0149 (13)	0.0001 (12)
C14	0.0354 (15)	0.0464 (18)	0.0322 (15)	0.0004 (13)	0.0092 (12)	0.0028 (13)
C15	0.0409 (17)	0.074 (3)	0.0398 (17)	0.0117 (16)	0.0243 (15)	0.0033 (16)

Geometric parameters (Å, º) top

Br1—C11	1.892 (3)	C7—C8	1.344 (5)
O1—C6	1.216 (4)	C7—H7A	0.9500
O2—C12	1.359 (3)	C8—C9	1.466 (4)
O2—C15	1.433 (4)	C8—H8A	0.9500
N1—C5	1.329 (5)	C9—C14	1.391 (5)
N1—C1	1.341 (4)	C9—C10	1.400 (5)
C1—C2	1.391 (4)	C10—C11	1.372 (4)
C1—C6	1.504 (5)	C10—H10A	0.9500
C2—C3	1.391 (5)	C11—C12	1.406 (4)
C2—H2A	0.9500	C12—C13	1.385 (4)
C3—C4	1.377 (5)	C13—C14	1.383 (5)
C3—H3A	0.9500	C13—H13A	0.9500
C4—C5	1.388 (5)	C14—H14A	0.9500
C4—H4A	0.9500	C15—H15A	0.9800
C5—H5A	0.9500	C15—H15B	0.9800
C6—C7	1.480 (4)	C15—H15C	0.9800

C12—O2—C15	116.6 (3)	C9—C8—H8A	116.8
C5—N1—C1	117.7 (3)	C14—C9—C10	117.9 (3)
N1—C1—C2	123.1 (3)	C14—C9—C8	119.6 (3)
N1—C1—C6	117.9 (3)	C10—C9—C8	122.4 (3)
C2—C1—C6	119.0 (3)	C11—C10—C9	120.0 (3)
C3—C2—C1	118.2 (3)	C11—C10—H10A	120.0
C3—C2—H2A	120.9	C9—C10—H10A	120.0
C1—C2—H2A	120.9	C10—C11—C12	121.7 (3)
C4—C3—C2	118.9 (3)	C10—C11—Br1	119.4 (2)
C4—C3—H3A	120.6	C12—C11—Br1	118.9 (2)
C2—C3—H3A	120.6	O2—C12—C13	125.2 (3)
C3—C4—C5	118.9 (3)	O2—C12—C11	116.5 (3)
C3—C4—H4A	120.5	C13—C12—C11	118.3 (3)
C5—C4—H4A	120.5	C14—C13—C12	119.8 (3)
N1—C5—C4	123.2 (3)	C14—C13—H13A	120.1
N1—C5—H5A	118.4	C12—C13—H13A	120.1
C4—C5—H5A	118.4	C13—C14—C9	122.2 (3)
O1—C6—C7	122.1 (3)	C13—C14—H14A	118.9
O1—C6—C1	121.5 (3)	C9—C14—H14A	118.9
C7—C6—C1	116.4 (3)	O2—C15—H15A	109.5
C8—C7—C6	121.0 (3)	O2—C15—H15B	109.5
C8—C7—H7A	119.5	H15A—C15—H15B	109.5
C6—C7—H7A	119.5	O2—C15—H15C	109.5
C7—C8—C9	126.3 (3)	H15A—C15—H15C	109.5
C7—C8—H8A	116.8	H15B—C15—H15C	109.5

C5—N1—C1—C2	−0.8 (5)	C7—C8—C9—C10	−7.5 (5)
C5—N1—C1—C6	179.2 (3)	C14—C9—C10—C11	0.1 (5)
N1—C1—C2—C3	0.1 (5)	C8—C9—C10—C11	177.7 (3)
C6—C1—C2—C3	−179.9 (3)	C9—C10—C11—C12	−1.8 (5)
C1—C2—C3—C4	0.8 (5)	C9—C10—C11—Br1	178.0 (2)
C2—C3—C4—C5	−0.9 (5)	C15—O2—C12—C13	−1.6 (5)
C1—N1—C5—C4	0.7 (5)	C15—O2—C12—C11	178.1 (3)
C3—C4—C5—N1	0.1 (5)	C10—C11—C12—O2	−177.6 (3)
N1—C1—C6—O1	179.6 (3)	Br1—C11—C12—O2	2.7 (4)
C2—C1—C6—O1	−0.4 (5)	C10—C11—C12—C13	2.2 (5)
N1—C1—C6—C7	−1.4 (4)	Br1—C11—C12—C13	−177.6 (2)
C2—C1—C6—C7	178.6 (3)	O2—C12—C13—C14	178.9 (3)
O1—C6—C7—C8	5.8 (6)	C11—C12—C13—C14	−0.9 (5)
C1—C6—C7—C8	−173.2 (3)	C12—C13—C14—C9	−0.8 (5)
C6—C7—C8—C9	−177.7 (3)	C10—C9—C14—C13	1.2 (5)
C7—C8—C9—C14	170.1 (3)	C8—C9—C14—C13	−176.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Br1ⁱ	0.95	3.04	3.870 (3)	146

Symmetry code: (i) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrNO₂
M_r	318.17
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	123
a, b, c (Å)	26.3402 (13), 3.8906 (2), 27.5826 (17)
β (°)	113.892 (5)
V (Å³)	2584.4 (2)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	4.31
Crystal size (mm)	0.49 × 0.21 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.535, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3978, 2556, 2431
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 1.08
No. of reflections	2556
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.64

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Br1ⁱ	0.95	3.04	3.870 (3)	146

Symmetry code: (i) x+1/2, y+1/2, z.

Acknowledgements

SS and BN thank Mangalore University and the UGC SAP for financial assistance for the purchase of chemicals. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

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