(E)-1-(4-Bromo­phen­yl)-3-(2,4,6-trimethoxy­phen­yl)prop-2-en-1-one

Chantrapromma, S.; Suwunwong, T.; Karalai, C.; Fun, H.-K.

doi:10.1107/S1600536809010496

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o893-o894

doi:10.1107/S1600536809010496

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(E)-1-(4-Bromophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one †

Suchada Chantrapromma,^a ^* Thitipone Suwunwong,^a Chatchanok Karalai ^a and Hoong-Kun Fun ^b ‡

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 9 March 2009; accepted 22 March 2009; online 28 March 2009)

The molecule of the title chalcone derivative, C₁₈H₁₇BrO₄, is twisted, the dihedral angle between the 4-bromophenyl and 2,4,6-trimethoxyphenyl rings being 39.17 (6)°. The three methoxy groups are oriented in two different conformations whereby two methoxy groups are coplanar, whereas the third is twisted with respect to the attached benzene ring [C—O—C—C torsion angles of −2.84 (18), −2.80 (18) and −9.31 (18)°]. Weak intramolecular C—H⋯O interactions generate two S(5) and one S(6) ring motifs. In the crystal structure, molecules are linked into supramolecular sheets parallel to the bc plane by weak C—H⋯O interactions. These sheets are stacked along the a axis. The crystal structure is further stabilized by weak C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For a related structure, see: Suwunwong et al. (2009 ). For background to and applications of chalcones, see: Fayed & Awad (2004 ); Jung et al. (2008 ); Patil & Dharmaprakash (2008 ); Prasad et al. (2008 ); Sens & Drexhage (1981 ) and Xu et al. (2005 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₁₈H₁₇BrO₄
M_r = 377.22
Triclinic, $[P \overline 1]$
a = 6.3690 (1) Å
b = 9.2553 (1) Å
c = 14.1884 (2) Å
α = 104.397 (1)°
β = 93.748 (1)°
γ = 98.799 (1)°
V = 795.88 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.60 mm⁻¹
T = 100 K
0.27 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.541, T_max = 0.701
16214 measured reflections
4607 independent reflections
4118 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.060
S = 1.02
4607 reflections
276 parameters
All H-atom parameters refined
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.925 (18)	2.497 (18)	3.3572 (17)	154.9 (15)
C8—H8⋯O4	0.920 (18)	2.268 (18)	2.8103 (16)	117.2 (14)
C9—H9⋯O1	0.936 (18)	2.449 (19)	2.8128 (17)	103.1 (13)
C9—H9⋯O2	0.936 (18)	2.269 (19)	2.6960 (16)	107.1 (14)
C18—H18A⋯O1ⁱⁱ	0.968 (19)	2.566 (19)	3.4518 (18)	152.1 (15)
C17—H17C⋯Cg1ⁱⁱⁱ	0.971 (17)	2.754 (18)	3.6601 (14)	155.6 (14)
Symmetry codes: (i) x+1, y-1, z; (ii) x, y+1, z; (iii) -x, -y+1, -z+2. Cg1 is the centroid of the C10–C15 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010496/sj2593sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010496/sj2593Isup2.hkl

checkCIF report

Comment top

Chalcones are compounds which have a wide range of applications such as in non-linear optical (Patil & Dharmaprakash, 2008) and electro-active fluorescent materials (Jung et al., 2008) or materials with various biological activities (Prasad et al., 2008). Fluorescent compounds are used for various applications such as fluorescent dyes (Fayed & Awad, 2004), light-emitting diodes, LEDs, (Sens & Drexhage, 1981) and fluorescent probes (Xu et al., 2005). In general, fluorescent materials are aromatic compounds which are conjugated with a double bond and/or aliphatic/alicyclic carbonyl groups typified by the structures of chalcone derivatives. These interesting properties prompted us to synthesize the title chalcone derivative in order to study its fluorescent properties and to compare these properties with those of a closely related structure (Suwunwong et al., 2009). We report here the crystal structure of the title compound (I).

The molecule of (I) in Fig. 1 exists in an E configuration with respect to the C8//db C9 double bond [1.3486 (18) Å]. The molecule is twisted with the interplanar angle between the 4-bromophenyl and the 2,4,6-trimethoxyphenyl rings being 39.17 (6)° compared to the corresponding angle of 44.18 (6)° between the 4-bromophenyl and the 3,4,5-trimethoxyphenyl ring in the closely related structure, 2E-1-(4-bromophenyl)-3-(3,4,5-trimethoxyphenyl) prop-2-en-1-one (II) (Suwunwong et al., 2009). Atoms O1, C6, C7 and C8 lie on the same plane with a maximum deviation of -0.001 (1) Å for atom C7 and the mean plane through them makes dihedral angles of 27.54 (7)° and 12.35 (7)° with the 4-bromophenyl and the 2,4,6-trimethoxyphenyl rings, respectively. The three methoxy groups of the 2,4,6-trimethoxyphenyl unit adopt two different orientations. The C13 and C15 methoxy groups are co-planar with the attached benzene ring with torsion angles C17–O3–C13–C12 = -2.84 (18)° and C18–O4–C15–C14 = -2.80 (18)° whereas the C11 group is twisted with a torsion angle C16–O2–C11–C12 = -9.31 (18)° indicating (-)-syn-periplanar conformations. Weak intramolecular C9—H9···O1 and C9—H9···O2 interactions generate S(5) ring motifs whereas a weak intramolecular C8—H8···O4 interaction generates an S(6) ring motif (Bernstein et al., 1995) (Table 1). The different substitutional positions of the three methoxy groups in 2,4,6-trimethoxyphenyl of (I) compared to the 3,4,5-trimethoxy groups in (II) (Suwunwong et al., 2009), produced different weak intramolecular C—H···O interactions especially the weak C9—H9···O2 and C9—H9···O4 intramolecular interactions which help the molecule of (I) to be less twisted. Bond distances in the molecule are normal (Allen et al., 1987) and are comparable with those in the closely related structure (Suwunwong et al., 2009).

In the crystal packing (Fig. 2), molecules are linked by weak intermolcular C5—H5···O3 (symmetry code: 1 + x, -1 + y, z) and C18—H18A···O1 (symmetry code: x, 1 + y, z) interactions (Table 1) into supramolecular sheets parallel to the bc plane. These sheets are stacked along the a axis. The crystal structure is further stabilized by weak C—H···π interactions (Table 1); Cg1 is the centroid of the C10–C15 ring.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For a related structure, see: Suwunwong et al. (2009). For background to and applications of chalcones, see: Fayed & Awad (2004); Jung et al. (2008); Patil & Dharmaprakash (2008); Prasad et al. (2008); Sens & Drexhage (1981) and Xu et al. (2005). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986). Cg1 is the centroid of the C10–C15 ring.

Experimental top

The title compound was synthesized by the condensation of 2,4,6-trimethoxybenzaldehyde (0.4 g, 2 mmol) with 4-bromoacetophenone (0.4 g, 2 mmol) in ethanol (30 ml) in the presence of 10% NaOH(aq) (5 ml). After stirring for 4 h in an ice bath (278 K), a pale yellow solid appeared after leaving the mixture at room temperature for 4 h. The resulting pale yellow solid was collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Pale yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from acetone/ethanol (1:1 v/v) by slow evaporation of the solvent at room temperature over several days, Mp. 425–426 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, showing supramolecular sheets. Hydrogen bonds are shown as dashed lines.

(E)-1-(4-Bromophenyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₇BrO₄	Z = 2
M_r = 377.22	F(000) = 384
Triclinic, P1	D_x = 1.574 Mg m⁻³
Hall symbol: -P 1	Melting point = 425–426 K
a = 6.3690 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2553 (1) Å	Cell parameters from 4607 reflections
c = 14.1884 (2) Å	θ = 2.3–30.0°
α = 104.397 (1)°	µ = 2.60 mm⁻¹
β = 93.748 (1)°	T = 100 K
γ = 98.799 (1)°	Block, colorless
V = 795.88 (2) Å³	0.27 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4607 independent reflections
Radiation source: sealed tube	4118 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.541, T_max = 0.701	k = −13→13
16214 measured reflections	l = −19→19

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.060	All H-atom parameters refined
S = 1.02	w = 1/[σ²(F_o²) + (0.029P)² + 0.2809P] where P = (F_o² + 2F_c²)/3
4607 reflections	(Δ/σ)_max = 0.001
276 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₇BrO₄	γ = 98.799 (1)°
M_r = 377.22	V = 795.88 (2) Å³
Triclinic, P1	Z = 2
a = 6.3690 (1) Å	Mo Kα radiation
b = 9.2553 (1) Å	µ = 2.60 mm⁻¹
c = 14.1884 (2) Å	T = 100 K
α = 104.397 (1)°	0.27 × 0.20 × 0.15 mm
β = 93.748 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4607 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4118 reflections with I > 2σ(I)
T_min = 0.541, T_max = 0.701	R_int = 0.023
16214 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.060	All H-atom parameters refined
S = 1.02	Δρ_max = 0.42 e Å⁻³
4607 reflections	Δρ_min = −0.23 e Å⁻³
276 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	1.13952 (2)	−0.293272 (16)	0.461372 (11)	0.02616 (5)
O1	0.44064 (16)	−0.15866 (11)	0.80334 (7)	0.0216 (2)
O2	−0.08941 (16)	0.10051 (10)	0.90599 (7)	0.01977 (19)
O3	−0.16385 (15)	0.59990 (10)	0.87549 (7)	0.01789 (18)
O4	0.35439 (15)	0.34158 (10)	0.71793 (7)	0.01744 (18)
C1	0.6621 (2)	−0.08380 (15)	0.59115 (10)	0.0193 (2)
C2	0.8032 (2)	−0.13463 (16)	0.52476 (10)	0.0213 (3)
C3	0.9448 (2)	−0.22219 (14)	0.55005 (10)	0.0184 (2)
C4	0.9487 (2)	−0.25950 (15)	0.63902 (10)	0.0197 (3)
C5	0.8037 (2)	−0.21054 (14)	0.70324 (10)	0.0183 (2)
C6	0.6585 (2)	−0.12259 (13)	0.67994 (9)	0.0153 (2)
C7	0.4967 (2)	−0.07889 (14)	0.74854 (9)	0.0158 (2)
C8	0.4106 (2)	0.06017 (14)	0.74754 (9)	0.0168 (2)
C9	0.2408 (2)	0.08983 (14)	0.79633 (9)	0.0154 (2)
C10	0.13257 (19)	0.21967 (13)	0.81164 (9)	0.0141 (2)
C11	−0.0378 (2)	0.22448 (13)	0.87113 (9)	0.0147 (2)
C12	−0.1436 (2)	0.34794 (14)	0.89404 (9)	0.0155 (2)
C13	−0.0755 (2)	0.47186 (14)	0.85774 (9)	0.0145 (2)
C14	0.0926 (2)	0.47405 (14)	0.79966 (9)	0.0153 (2)
C15	0.19197 (19)	0.34849 (13)	0.77554 (9)	0.0139 (2)
C16	−0.2346 (2)	0.10739 (16)	0.97956 (10)	0.0194 (3)
C17	−0.3435 (2)	0.60468 (16)	0.93123 (10)	0.0196 (3)
C18	0.4171 (2)	0.46747 (15)	0.67761 (11)	0.0198 (3)
H1	0.562 (3)	−0.026 (2)	0.5736 (13)	0.027 (4)*
H2	0.802 (3)	−0.108 (2)	0.4646 (14)	0.029 (5)*
H4	1.047 (3)	−0.321 (2)	0.6562 (13)	0.027 (4)*
H5	0.809 (3)	−0.2327 (19)	0.7633 (13)	0.024 (4)*
H8	0.481 (3)	0.1247 (19)	0.7154 (12)	0.017 (4)*
H9	0.185 (3)	0.0164 (19)	0.8273 (12)	0.021 (4)*
H12	−0.257 (3)	0.3470 (19)	0.9351 (13)	0.022 (4)*
H14	0.134 (3)	0.5637 (19)	0.7793 (12)	0.020 (4)*
H16A	−0.182 (3)	0.1914 (19)	1.0344 (13)	0.022 (4)*
H16B	−0.233 (3)	0.011 (2)	0.9971 (14)	0.030 (5)*
H16C	−0.379 (3)	0.1129 (18)	0.9542 (12)	0.016 (4)*
H17A	−0.383 (3)	0.700 (2)	0.9308 (14)	0.030 (5)*
H17B	−0.455 (3)	0.5210 (19)	0.8990 (12)	0.020 (4)*
H17C	−0.302 (3)	0.6012 (18)	0.9976 (13)	0.020 (4)*
H18A	0.456 (3)	0.561 (2)	0.7289 (14)	0.028 (5)*
H18B	0.535 (3)	0.444 (2)	0.6459 (14)	0.029 (5)*
H18C	0.302 (3)	0.4758 (19)	0.6301 (13)	0.023 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02155 (8)	0.02786 (8)	0.02793 (8)	0.00852 (5)	0.00972 (5)	0.00087 (5)
O1	0.0250 (5)	0.0186 (4)	0.0258 (5)	0.0072 (4)	0.0092 (4)	0.0105 (4)
O2	0.0227 (5)	0.0166 (4)	0.0246 (5)	0.0054 (4)	0.0119 (4)	0.0106 (4)
O3	0.0185 (5)	0.0176 (4)	0.0220 (5)	0.0089 (3)	0.0091 (4)	0.0081 (4)
O4	0.0197 (5)	0.0152 (4)	0.0211 (4)	0.0062 (3)	0.0102 (4)	0.0078 (3)
C1	0.0199 (6)	0.0216 (6)	0.0183 (6)	0.0097 (5)	0.0017 (5)	0.0053 (5)
C2	0.0223 (7)	0.0260 (7)	0.0170 (6)	0.0081 (5)	0.0033 (5)	0.0054 (5)
C3	0.0158 (6)	0.0168 (6)	0.0204 (6)	0.0033 (5)	0.0036 (5)	0.0002 (5)
C4	0.0178 (6)	0.0161 (6)	0.0271 (7)	0.0065 (5)	0.0030 (5)	0.0067 (5)
C5	0.0196 (6)	0.0161 (6)	0.0213 (6)	0.0046 (5)	0.0031 (5)	0.0076 (5)
C6	0.0154 (6)	0.0118 (5)	0.0180 (6)	0.0021 (4)	0.0021 (4)	0.0027 (4)
C7	0.0168 (6)	0.0140 (5)	0.0164 (6)	0.0031 (4)	0.0018 (4)	0.0030 (4)
C8	0.0203 (6)	0.0137 (5)	0.0176 (6)	0.0044 (5)	0.0042 (5)	0.0051 (4)
C9	0.0171 (6)	0.0131 (5)	0.0158 (6)	0.0022 (4)	0.0013 (4)	0.0039 (4)
C10	0.0143 (6)	0.0141 (5)	0.0137 (5)	0.0023 (4)	0.0021 (4)	0.0031 (4)
C11	0.0155 (6)	0.0137 (5)	0.0149 (5)	0.0012 (4)	0.0019 (4)	0.0049 (4)
C12	0.0143 (6)	0.0175 (6)	0.0155 (6)	0.0037 (4)	0.0038 (4)	0.0047 (4)
C13	0.0143 (6)	0.0149 (5)	0.0149 (5)	0.0047 (4)	0.0011 (4)	0.0036 (4)
C14	0.0171 (6)	0.0147 (5)	0.0157 (6)	0.0040 (4)	0.0035 (4)	0.0057 (4)
C15	0.0135 (5)	0.0151 (5)	0.0132 (5)	0.0027 (4)	0.0030 (4)	0.0036 (4)
C16	0.0197 (6)	0.0206 (6)	0.0203 (6)	0.0026 (5)	0.0082 (5)	0.0087 (5)
C17	0.0172 (6)	0.0228 (6)	0.0212 (6)	0.0076 (5)	0.0070 (5)	0.0061 (5)
C18	0.0229 (7)	0.0165 (6)	0.0244 (7)	0.0062 (5)	0.0125 (5)	0.0093 (5)

Geometric parameters (Å, º) top

Br1—C3	1.8963 (13)	C8—H8	0.920 (17)
O1—C7	1.2321 (15)	C9—C10	1.4524 (17)
O2—C11	1.3627 (14)	C9—H9	0.936 (17)
O2—C16	1.4351 (15)	C10—C11	1.4171 (17)
O3—C13	1.3634 (15)	C10—C15	1.4205 (16)
O3—C17	1.4326 (16)	C11—C12	1.3943 (17)
O4—C15	1.3591 (14)	C12—C13	1.3927 (17)
O4—C18	1.4364 (15)	C12—H12	0.957 (18)
C1—C2	1.3910 (19)	C13—C14	1.3937 (17)
C1—C6	1.3939 (18)	C14—C15	1.3870 (17)
C1—H1	0.953 (18)	C14—H14	0.950 (17)
C2—C3	1.388 (2)	C16—H16A	0.953 (18)
C2—H2	0.943 (19)	C16—H16B	0.985 (19)
C3—C4	1.3888 (19)	C16—H16C	0.980 (17)
C4—C5	1.3858 (19)	C17—H17A	0.956 (18)
C4—H4	0.965 (18)	C17—H17B	0.961 (17)
C5—C6	1.3969 (18)	C17—H17C	0.971 (17)
C5—H5	0.924 (18)	C18—H18A	0.971 (19)
C6—C7	1.4954 (17)	C18—H18B	0.93 (2)
C7—C8	1.4768 (17)	C18—H18C	0.987 (18)
C8—C9	1.3486 (18)

C11—O2—C16	118.40 (10)	O2—C11—C12	122.08 (11)
C13—O3—C17	118.06 (10)	O2—C11—C10	115.23 (11)
C15—O4—C18	117.90 (10)	C12—C11—C10	122.69 (11)
C2—C1—C6	121.15 (12)	C13—C12—C11	118.12 (11)
C2—C1—H1	118.8 (11)	C13—C12—H12	121.9 (10)
C6—C1—H1	120.0 (11)	C11—C12—H12	120.0 (10)
C3—C2—C1	118.35 (13)	O3—C13—C12	123.91 (11)
C3—C2—H2	121.6 (11)	O3—C13—C14	114.39 (11)
C1—C2—H2	120.1 (11)	C12—C13—C14	121.70 (11)
C2—C3—C4	121.82 (13)	C15—C14—C13	119.29 (11)
C2—C3—Br1	119.49 (10)	C15—C14—H14	123.6 (10)
C4—C3—Br1	118.70 (10)	C13—C14—H14	117.1 (10)
C5—C4—C3	118.94 (12)	O4—C15—C14	122.54 (11)
C5—C4—H4	119.5 (11)	O4—C15—C10	115.72 (10)
C3—C4—H4	121.5 (11)	C14—C15—C10	121.72 (11)
C4—C5—C6	120.70 (12)	O2—C16—H16A	110.1 (11)
C4—C5—H5	118.9 (11)	O2—C16—H16B	102.7 (11)
C6—C5—H5	120.4 (11)	H16A—C16—H16B	110.8 (15)
C1—C6—C5	119.01 (12)	O2—C16—H16C	112.1 (10)
C1—C6—C7	121.73 (11)	H16A—C16—H16C	110.4 (14)
C5—C6—C7	119.20 (11)	H16B—C16—H16C	110.5 (14)
O1—C7—C8	122.63 (12)	O3—C17—H17A	103.5 (11)
O1—C7—C6	119.49 (11)	O3—C17—H17B	108.7 (10)
C8—C7—C6	117.87 (11)	H17A—C17—H17B	112.0 (15)
C9—C8—C7	119.33 (11)	O3—C17—H17C	110.5 (10)
C9—C8—H8	123.4 (10)	H17A—C17—H17C	110.8 (15)
C7—C8—H8	117.2 (10)	H17B—C17—H17C	111.1 (14)
C8—C9—C10	130.75 (12)	O4—C18—H18A	111.0 (11)
C8—C9—H9	115.1 (11)	O4—C18—H18B	104.2 (11)
C10—C9—H9	114.1 (11)	H18A—C18—H18B	110.1 (15)
C11—C10—C15	116.44 (11)	O4—C18—H18C	110.9 (10)
C11—C10—C9	118.69 (11)	H18A—C18—H18C	110.4 (15)
C15—C10—C9	124.78 (11)	H18B—C18—H18C	110.0 (15)

C6—C1—C2—C3	−1.6 (2)	C15—C10—C11—O2	−179.05 (11)
C1—C2—C3—C4	0.0 (2)	C9—C10—C11—O2	−2.38 (17)
C1—C2—C3—Br1	−179.94 (10)	C15—C10—C11—C12	−0.09 (18)
C2—C3—C4—C5	1.4 (2)	C9—C10—C11—C12	176.58 (12)
Br1—C3—C4—C5	−178.66 (10)	O2—C11—C12—C13	177.93 (11)
C3—C4—C5—C6	−1.2 (2)	C10—C11—C12—C13	−0.96 (19)
C2—C1—C6—C5	1.8 (2)	C17—O3—C13—C12	−2.84 (18)
C2—C1—C6—C7	−175.19 (12)	C17—O3—C13—C14	177.45 (11)
C4—C5—C6—C1	−0.4 (2)	C11—C12—C13—O3	−179.38 (11)
C4—C5—C6—C7	176.71 (12)	C11—C12—C13—C14	0.31 (19)
C1—C6—C7—O1	151.49 (13)	O3—C13—C14—C15	−178.89 (11)
C5—C6—C7—O1	−25.51 (18)	C12—C13—C14—C15	1.40 (19)
C1—C6—C7—C8	−28.65 (18)	C18—O4—C15—C14	−2.80 (18)
C5—C6—C7—C8	154.35 (12)	C18—O4—C15—C10	178.51 (11)
O1—C7—C8—C9	−10.8 (2)	C13—C14—C15—O4	178.88 (11)
C6—C7—C8—C9	169.35 (12)	C13—C14—C15—C10	−2.52 (19)
C7—C8—C9—C10	176.36 (12)	C11—C10—C15—O4	−179.45 (10)
C8—C9—C10—C11	−176.74 (13)	C9—C10—C15—O4	4.10 (18)
C8—C9—C10—C15	−0.4 (2)	C11—C10—C15—C14	1.86 (18)
C16—O2—C11—C12	−9.31 (18)	C9—C10—C15—C14	−174.59 (12)
C16—O2—C11—C10	169.65 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.925 (18)	2.497 (18)	3.3572 (17)	154.9 (15)
C8—H8···O4	0.920 (18)	2.268 (18)	2.8103 (16)	117.2 (14)
C9—H9···O1	0.936 (18)	2.449 (19)	2.8128 (17)	103.1 (13)
C9—H9···O2	0.936 (18)	2.269 (19)	2.6960 (16)	107.1 (14)
C18—H18A···O1ⁱⁱ	0.968 (19)	2.566 (19)	3.4518 (18)	152.1 (15)
C17—H17C···Cg1ⁱⁱⁱ	0.971 (17)	2.754 (18)	3.6601 (14)	155.6 (14)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇BrO₄
M_r	377.22
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.3690 (1), 9.2553 (1), 14.1884 (2)
α, β, γ (°)	104.397 (1), 93.748 (1), 98.799 (1)
V (Å³)	795.88 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.60
Crystal size (mm)	0.27 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.541, 0.701
No. of measured, independent and observed [I > 2σ(I)] reflections	16214, 4607, 4118
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.060, 1.02
No. of reflections	4607
No. of parameters	276
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.925 (18)	2.497 (18)	3.3572 (17)	154.9 (15)
C8—H8···O4	0.920 (18)	2.268 (18)	2.8103 (16)	117.2 (14)
C9—H9···O1	0.936 (18)	2.449 (19)	2.8128 (17)	103.1 (13)
C9—H9···O2	0.936 (18)	2.269 (19)	2.6960 (16)	107.1 (14)
C18—H18A···O1ⁱⁱ	0.968 (19)	2.566 (19)	3.4518 (18)	152.1 (15)
C17—H17C···Cg1ⁱⁱⁱ	0.971 (17)	2.754 (18)	3.6601 (14)	155.6 (14)

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

Footnotes

†This paper is dedicated to the late Her Royal Highness Princess Galyani Vadhana Krom Luang Naradhiwas Rajanagarindra for her patronage of Science in Thailand.

‡Additional correspondence author, email: hkfun@usm.my.

Acknowledgements

The authors thank Prince of Songkla University for financial support through the Crystal Materials Research Unit and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. TS thanks the Graduate School, Prince of Songkla University for partial financial support.

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