(2E)-1-(2-Bromo­phen­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S160053681002235X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1676

doi:10.1107/S160053681002235X

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(2E)-1-(2-Bromophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

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

^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, ^dDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^eDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: jjasinski@keene.edu

(Received 9 June 2010; accepted 10 June 2010; online 16 June 2010)

In the chalcone title compound, C₁₈H₁₇BrO₄, the dihedral angle between the mean planes of the 2-bromo- and 3,4,5-trimethoxy-substituted benzene rings is 89.3 (1)°. The angles between the mean plane of the prop-2-en-1-one group and the 2-bromophenyl and 3,4,5-trimethoxyphenyl ring planes are 59.7 (1) and 40.5 (8)°, respectively. While no classical hydrogen bonds are present, three weak intermolecular C—H⋯O interactions and weak C—H⋯Br and C—H⋯Cg π-ring stacking interactions [C—H⋯Cg distance = 3.377 (2) Å] are observed, which contribute to the stability of crystal packing.

Related literature

For the radical quenching properties of included phenol groups, see: Dhar (1981 ). For the anticancer activity of chalcones, see: Dimmock et al. (1999 ). For related structures, see: Chantrapromma et al. (2009 ); Patil et al. (2006 ); Suwunwong et al. (2009 ). For bond distances and angles, see: Allen (2002 ).

Experimental

Crystal data

C₁₈H₁₇BrO₄
M_r = 377.23
Orthorhombic, P b c a
a = 9.9616 (4) Å
b = 13.6020 (13) Å
c = 24.4162 (17) Å
V = 3308.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.50 mm⁻¹
T = 110 K
0.47 × 0.42 × 0.31 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.499, T_max = 1.000
8122 measured reflections
3296 independent reflections
2940 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.04
3296 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1ⁱ	0.95	2.44	3.233 (3)	140
C9—H9A⋯O2ⁱⁱ	0.95	2.51	3.308 (3)	141
C15—H15A⋯O2ⁱⁱ	0.95	2.53	3.202 (2)	128
C17—H17C⋯Br1ⁱⁱⁱ	0.98	2.99	3.746 (2)	135
C17—H17A⋯Cg2^iv	0.98	2.83	3.379 (2)	125
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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/S160053681002235X/fj2317sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681002235X/fj2317Isup2.hkl

checkCIF report

Comment top

Chalcones, or 1,3-diaryl-2-propen-1-ones, belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenol groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones have been reported to possess many useful biological properties, including anti-inflammatory,antimicrobial, antifungal, antioxidant, cytotoxic, anticancer activities (Dimmock et al., 1999). The crystal structures of some closely related chalcones, viz., (E)-1-(4-bromophenyl)-3-(3,4,5-trimethoxy-phenyl)prop-2-en-1-one (Suwunwong et al., 2009), (E)-1-(4-bromophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one (Chantrapromma et al., 2009) and 1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (Patil et al., 2006) have been reported. Hence in continuation with the synthesis and crystal structure determination and also owing to the importance of these flavanoid analogs, this new bromo-trimethoxy substituted chalcone, (I), C₁₈H₁₇BrO₄, is synthesized and its crystal structure is reported.

The title compound, (I), C₁₈H₁₇BrO₄,is a chalcone with 2-bromophenyl and 3,4,5-trimethoxyphenyl rings bonded at opposite sides of a propene group (Fig. 2). The dihedral angle between mean planes of the benzene rings in the ortho-bromo and meta- para-trimethoxy substituted rings is 89.3 (1)°. The angles between the mean plane of the prop-2-ene-1-one group (C1/C7/O1/C8) and the mean planes of the benzene rings in the 2-bromophenyl (C1–C6)and 3,4,5-trimethoxyphenyl rings (C10—C15) are 59.7 (1)° and 40.5 (8)°, respectively. Bond distances and angles are in normal ranges (Allen, 2002). While no classical hydrogen bonds are present, three weak intermolecular C—H···O interactions (Fig. 3) and weak C—H···Br (Table 1) and C17—H17A···Cg2 π-ring stacking interactions (H17A···Cg2 = 2.83 Å; H17A–Perp = 2.82 Å; C17—H17A···Cg2 = 125°; C17···Cg2—H17A = 3.379 (2) Å; Cg2 = C10–C15) are observed which contribute to the stability of crystal packing.

Related literature top

For radical quenching properties of included phenol groups, see: Dhar (1981). For the anticancer activities [of?], see: Dimmock et al. (1999). For a related structure, see: Chantrapromma et al. (2009); Patil et al. (2006); Suwunwong et al. (2009). For bond distances and angles, see : Allen (2002).

Experimental top

A 50% KOH solution was added to a mixture of 2-bromo acetophenone (0.01 mol, 1.99 g) and 3,4,5-trimethoxy benzaldehyde (0.01 mol, 1.96 g) in 25 ml of ethanol (Fig. 1). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from ethyl acetate by slow evaporation method and yield of the compound was 45% (m.p.325–327 K). Analytical data: Found (Calculated) for C₁₈H₁₇BrO₄: C %: 57.26 (57.31%); H%: 4.49 (4.54%).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (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 the title compound.
	Fig. 2. Molecular structure of (I), C₁₈H₁₇BrO₄, showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 3. Packing diagram of the title compound, C₁₈H₁₇BrO₄, viewed down the a axis. Dashed lines indicate weak C—H···O intermolecular hydrogen bond interactions linking the molecules into chains along the (011).

(2E)-1-(2-Bromophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₇BrO₄	F(000) = 1536
M_r = 377.23	D_x = 1.515 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4251 reflections
a = 9.9616 (4) Å	θ = 4.4–74.1°
b = 13.6020 (13) Å	µ = 2.50 mm⁻¹
c = 24.4162 (17) Å	T = 110 K
V = 3308.4 (4) Å³	Chunk, colorless
Z = 8	0.47 × 0.42 × 0.31 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	3296 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2940 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 10.5081 pixels mm^-1	θ_max = 26.3°, θ_min = 2.6°
ω scans	h = −12→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→15
T_min = 0.499, T_max = 1.000	l = −30→28
8122 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0769P)² + 1.9413P] where P = (F_o² + 2F_c²)/3
3296 reflections	(Δ/σ)_max = 0.003
211 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

C₁₈H₁₇BrO₄	V = 3308.4 (4) Å³
M_r = 377.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.9616 (4) Å	µ = 2.50 mm⁻¹
b = 13.6020 (13) Å	T = 110 K
c = 24.4162 (17) Å	0.47 × 0.42 × 0.31 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	3296 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2940 reflections with I > 2σ(I)
T_min = 0.499, T_max = 1.000	R_int = 0.022
8122 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.04	Δρ_max = 0.46 e Å⁻³
3296 reflections	Δρ_min = −0.67 e Å⁻³
211 parameters

Special details top

Experimental. IR data (KBr) \v cm^-1: 2998 cm^-1, 2937 cm^-1, 2839 cm^-1 (C—H al. str), 3058 cm^-1 (C—H ar.str) 1646 cm^-1 (C=O), 1580 cm^-1 (C=C); 1245 cm^-1 (C—O—C).

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	0.74430 (2)	0.76760 (2)	0.612337 (10)	0.02659 (13)
O1	0.74217 (17)	0.57654 (14)	0.69518 (10)	0.0340 (5)
O2	0.31902 (16)	0.16171 (11)	0.60595 (6)	0.0191 (3)
O3	0.17918 (15)	0.20383 (11)	0.51830 (6)	0.0180 (3)
O4	0.14169 (16)	0.39311 (11)	0.48455 (6)	0.0203 (3)
C1	0.5557 (2)	0.68349 (15)	0.68770 (8)	0.0159 (4)
C2	0.6035 (2)	0.77077 (15)	0.66443 (8)	0.0169 (4)
C3	0.5453 (2)	0.86108 (16)	0.67668 (9)	0.0219 (4)
H3A	0.5798	0.9198	0.6610	0.026*
C4	0.4364 (2)	0.86455 (17)	0.71200 (9)	0.0255 (5)
H4A	0.3966	0.9260	0.7208	0.031*
C5	0.3854 (2)	0.77852 (17)	0.73449 (9)	0.0254 (5)
H5A	0.3101	0.7811	0.7584	0.031*
C6	0.4441 (2)	0.68889 (16)	0.72215 (9)	0.0203 (4)
H6A	0.4079	0.6303	0.7373	0.024*
C7	0.6256 (2)	0.58607 (16)	0.68075 (9)	0.0196 (4)
C8	0.5507 (2)	0.50263 (15)	0.65798 (9)	0.0183 (4)
H8A	0.5862	0.4384	0.6630	0.022*
C9	0.4355 (2)	0.51190 (14)	0.63061 (9)	0.0157 (4)
H9A	0.3975	0.5758	0.6282	0.019*
C10	0.3627 (2)	0.43154 (15)	0.60391 (8)	0.0149 (4)
C11	0.3777 (2)	0.33362 (15)	0.62149 (8)	0.0157 (4)
H11A	0.4324	0.3185	0.6522	0.019*
C12	0.3114 (2)	0.25927 (15)	0.59324 (9)	0.0151 (4)
C13	0.2319 (2)	0.28097 (16)	0.54734 (9)	0.0144 (4)
C14	0.2176 (2)	0.37893 (15)	0.53031 (9)	0.0158 (4)
C15	0.2808 (2)	0.45419 (15)	0.55925 (9)	0.0157 (4)
H15A	0.2681	0.5207	0.5486	0.019*
C16	0.3980 (2)	0.13512 (16)	0.65246 (10)	0.0242 (5)
H16A	0.3929	0.0639	0.6581	0.036*
H16B	0.3637	0.1690	0.6850	0.036*
H16C	0.4916	0.1542	0.6462	0.036*
C17	0.0357 (2)	0.19852 (18)	0.51743 (10)	0.0249 (5)
H17A	0.0077	0.1400	0.4970	0.037*
H17B	−0.0005	0.2574	0.4997	0.037*
H17C	0.0018	0.1945	0.5550	0.037*
C18	0.1511 (3)	0.48850 (18)	0.45889 (11)	0.0319 (6)
H18A	0.0980	0.4887	0.4251	0.048*
H18B	0.2452	0.5027	0.4502	0.048*
H18C	0.1165	0.5388	0.4839	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02410 (18)	0.0327 (2)	0.02294 (19)	−0.00535 (9)	0.00684 (8)	−0.00220 (9)
O1	0.0244 (9)	0.0223 (9)	0.0552 (13)	0.0010 (6)	−0.0201 (8)	−0.0062 (9)
O2	0.0224 (8)	0.0124 (7)	0.0226 (8)	−0.0033 (6)	−0.0055 (6)	0.0007 (6)
O3	0.0159 (7)	0.0188 (7)	0.0194 (7)	−0.0023 (6)	−0.0009 (6)	−0.0073 (6)
O4	0.0254 (8)	0.0187 (7)	0.0169 (7)	−0.0003 (6)	−0.0078 (6)	0.0006 (6)
C1	0.0177 (9)	0.0161 (10)	0.0138 (9)	−0.0046 (8)	−0.0051 (8)	−0.0020 (7)
C2	0.0177 (10)	0.0213 (11)	0.0117 (9)	−0.0025 (8)	0.0008 (8)	−0.0023 (7)
C3	0.0317 (12)	0.0159 (10)	0.0180 (10)	−0.0011 (9)	−0.0002 (9)	0.0020 (8)
C4	0.0342 (13)	0.0220 (11)	0.0204 (10)	0.0057 (10)	0.0026 (10)	−0.0045 (8)
C5	0.0251 (11)	0.0334 (13)	0.0178 (10)	−0.0009 (10)	0.0052 (9)	−0.0040 (9)
C6	0.0247 (10)	0.0207 (10)	0.0157 (10)	−0.0063 (9)	−0.0027 (8)	0.0007 (8)
C7	0.0208 (10)	0.0183 (10)	0.0197 (10)	−0.0017 (8)	−0.0051 (8)	0.0001 (8)
C8	0.0204 (10)	0.0117 (8)	0.0229 (11)	−0.0009 (8)	−0.0033 (9)	−0.0015 (8)
C9	0.0184 (10)	0.0126 (9)	0.0160 (10)	0.0005 (8)	0.0010 (8)	−0.0011 (7)
C10	0.0142 (9)	0.0141 (9)	0.0164 (9)	−0.0010 (8)	0.0018 (8)	−0.0034 (7)
C11	0.0152 (9)	0.0154 (9)	0.0163 (9)	0.0005 (8)	−0.0024 (8)	−0.0015 (8)
C12	0.0122 (9)	0.0150 (9)	0.0180 (10)	0.0000 (7)	0.0021 (8)	0.0008 (8)
C13	0.0116 (9)	0.0171 (10)	0.0144 (10)	−0.0023 (7)	0.0020 (7)	−0.0038 (8)
C14	0.0134 (8)	0.0194 (10)	0.0145 (9)	0.0019 (8)	0.0010 (8)	−0.0029 (8)
C15	0.0156 (8)	0.0133 (9)	0.0182 (10)	0.0028 (8)	0.0021 (8)	−0.0019 (8)
C16	0.0263 (11)	0.0166 (9)	0.0296 (12)	−0.0004 (9)	−0.0076 (10)	0.0053 (8)
C17	0.0171 (10)	0.0285 (12)	0.0290 (12)	−0.0073 (9)	−0.0057 (9)	0.0013 (9)
C18	0.0448 (15)	0.0260 (12)	0.0251 (12)	−0.0022 (11)	−0.0135 (11)	0.0079 (9)

Geometric parameters (Å, º) top

Br1—C2	1.894 (2)	C8—H8A	0.9500
O1—C7	1.221 (3)	C9—C10	1.465 (3)
O2—C12	1.365 (2)	C9—H9A	0.9500
O2—C16	1.428 (3)	C10—C15	1.396 (3)
O3—C13	1.371 (2)	C10—C11	1.407 (3)
O3—C17	1.431 (3)	C11—C12	1.391 (3)
O4—C14	1.363 (3)	C11—H11A	0.9500
O4—C18	1.444 (3)	C12—C13	1.404 (3)
C1—C6	1.396 (3)	C13—C14	1.403 (3)
C1—C2	1.400 (3)	C14—C15	1.394 (3)
C1—C7	1.506 (3)	C15—H15A	0.9500
C2—C3	1.391 (3)	C16—H16A	0.9800
C3—C4	1.386 (3)	C16—H16B	0.9800
C3—H3A	0.9500	C16—H16C	0.9800
C4—C5	1.389 (3)	C17—H17A	0.9800
C4—H4A	0.9500	C17—H17B	0.9800
C5—C6	1.385 (3)	C17—H17C	0.9800
C5—H5A	0.9500	C18—H18A	0.9800
C6—H6A	0.9500	C18—H18B	0.9800
C7—C8	1.468 (3)	C18—H18C	0.9800
C8—C9	1.334 (3)

C12—O2—C16	117.25 (16)	C12—C11—C10	119.09 (19)
C13—O3—C17	115.38 (17)	C12—C11—H11A	120.5
C14—O4—C18	116.55 (17)	C10—C11—H11A	120.5
C6—C1—C2	118.09 (19)	O2—C12—C11	124.57 (19)
C6—C1—C7	118.82 (18)	O2—C12—C13	114.68 (18)
C2—C1—C7	122.91 (19)	C11—C12—C13	120.74 (19)
C3—C2—C1	121.3 (2)	O3—C13—C14	122.3 (2)
C3—C2—Br1	118.25 (16)	O3—C13—C12	117.91 (19)
C1—C2—Br1	120.35 (15)	C14—C13—C12	119.56 (19)
C4—C3—C2	119.3 (2)	O4—C14—C15	124.20 (19)
C4—C3—H3A	120.3	O4—C14—C13	115.69 (18)
C2—C3—H3A	120.3	C15—C14—C13	120.1 (2)
C3—C4—C5	120.3 (2)	C14—C15—C10	119.83 (19)
C3—C4—H4A	119.9	C14—C15—H15A	120.1
C5—C4—H4A	119.9	C10—C15—H15A	120.1
C6—C5—C4	120.0 (2)	O2—C16—H16A	109.5
C6—C5—H5A	120.0	O2—C16—H16B	109.5
C4—C5—H5A	120.0	H16A—C16—H16B	109.5
C5—C6—C1	120.9 (2)	O2—C16—H16C	109.5
C5—C6—H6A	119.5	H16A—C16—H16C	109.5
C1—C6—H6A	119.5	H16B—C16—H16C	109.5
O1—C7—C8	120.7 (2)	O3—C17—H17A	109.5
O1—C7—C1	120.0 (2)	O3—C17—H17B	109.5
C8—C7—C1	119.23 (18)	H17A—C17—H17B	109.5
C9—C8—C7	123.64 (19)	O3—C17—H17C	109.5
C9—C8—H8A	118.2	H17A—C17—H17C	109.5
C7—C8—H8A	118.2	H17B—C17—H17C	109.5
C8—C9—C10	125.33 (18)	O4—C18—H18A	109.5
C8—C9—H9A	117.3	O4—C18—H18B	109.5
C10—C9—H9A	117.3	H18A—C18—H18B	109.5
C15—C10—C11	120.61 (19)	O4—C18—H18C	109.5
C15—C10—C9	118.17 (18)	H18A—C18—H18C	109.5
C11—C10—C9	121.18 (19)	H18B—C18—H18C	109.5

C6—C1—C2—C3	2.4 (3)	C9—C10—C11—C12	−177.03 (19)
C7—C1—C2—C3	−172.66 (19)	C16—O2—C12—C11	1.8 (3)
C6—C1—C2—Br1	−174.42 (15)	C16—O2—C12—C13	−179.68 (19)
C7—C1—C2—Br1	10.5 (3)	C10—C11—C12—O2	179.33 (19)
C1—C2—C3—C4	−1.0 (3)	C10—C11—C12—C13	0.9 (3)
Br1—C2—C3—C4	175.89 (17)	C17—O3—C13—C14	−68.0 (3)
C2—C3—C4—C5	−0.6 (3)	C17—O3—C13—C12	117.1 (2)
C3—C4—C5—C6	0.7 (4)	O2—C12—C13—O3	−4.5 (3)
C4—C5—C6—C1	0.8 (3)	C11—C12—C13—O3	174.12 (18)
C2—C1—C6—C5	−2.3 (3)	O2—C12—C13—C14	−179.56 (18)
C7—C1—C6—C5	173.0 (2)	C11—C12—C13—C14	−1.0 (3)
C6—C1—C7—O1	−117.3 (3)	C18—O4—C14—C15	13.2 (3)
C2—C1—C7—O1	57.7 (3)	C18—O4—C14—C13	−165.9 (2)
C6—C1—C7—C8	60.9 (3)	O3—C13—C14—O4	3.4 (3)
C2—C1—C7—C8	−124.0 (2)	C12—C13—C14—O4	178.29 (18)
O1—C7—C8—C9	−164.7 (2)	O3—C13—C14—C15	−175.64 (18)
C1—C7—C8—C9	17.1 (3)	C12—C13—C14—C15	−0.8 (3)
C7—C8—C9—C10	175.4 (2)	O4—C14—C15—C10	−176.39 (19)
C8—C9—C10—C15	−153.2 (2)	C13—C14—C15—C10	2.6 (3)
C8—C9—C10—C11	24.9 (3)	C11—C10—C15—C14	−2.7 (3)
C15—C10—C11—C12	1.0 (3)	C9—C10—C15—C14	175.34 (19)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ⁱ	0.95	2.44	3.233 (3)	140
C9—H9A···O2ⁱⁱ	0.95	2.51	3.308 (3)	141
C15—H15A···O2ⁱⁱ	0.95	2.53	3.202 (2)	128
C17—H17C···Br1ⁱⁱⁱ	0.98	2.99	3.746 (2)	135
C17—H17A···Cg2^iv	0.98	2.83	3.379 (2)	125

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇BrO₄
M_r	377.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	110
a, b, c (Å)	9.9616 (4), 13.6020 (13), 24.4162 (17)
V (Å³)	3308.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.50
Crystal size (mm)	0.47 × 0.42 × 0.31

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.499, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8122, 3296, 2940
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.04
No. of reflections	3296
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.67

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ⁱ	0.95	2.44	3.233 (3)	140
C9—H9A···O2ⁱⁱ	0.95	2.51	3.308 (3)	141
C15—H15A···O2ⁱⁱ	0.95	2.53	3.202 (2)	128
C17—H17C···Br1ⁱⁱⁱ	0.98	2.99	3.746 (2)	135
C17—H17A···Cg2^iv	0.98	2.83	3.379 (2)	125

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, −y+1/2, −z+1.

Acknowledgements

KV thanks UGC for a Junior Research Fellowship and for an SAP chemical grant. HSY thanks UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

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Patil, P. S., Rosli, M. M., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o4644–o4645. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 66| Part 7| July 2010| Page o1676

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