organic compounds
(E)-1-(5-Bromothiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
aInstitute of Pharmacy, GITAM University, Visakhapatnam-45, Andhrapradesh, India, bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and cKaruna College of Pharmacy, Thirumittacode, Palakad 679 533, Kerala, India
*Correspondence e-mail: vsb.gip@gitam.in
In the title compound, C16H15BrO4S, the dihedral angle between the thiophene and benzene rings is 13.08 (16)°. The C atoms of the meta methoxy groups of the substituted benzene ring lie close to the plane of the ring [displacements = 0.049 (5) and −0.022 (4) Å], whereas the para-C atom is significantly displaced [−1.052 (4) Å]. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming C(11) chains propagating in [100].
Related literature
For general background to et al. (2001); Horng et al. (2003); Mei et al. (2003).
see: ChunExperimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010); cell CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536811049294/hb6511sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049294/hb6511Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811049294/hb6511Isup3.cml
A mixture of 2-acetyl-5-BromoThiophene (0.01 mole) and 3,4,5-trimethoxybenzaldehyde (0.01 mole) were stirred in ethanol (30 ml) and then an aqueous solution of potassium hydroxide (40%,15 ml)was added to it. The mixture was kept over night at room temperature and then it was poured into crushed ice and acidified with dilute hydrochloric acid. The precipiteted chalcone was filtered and crystallized from ethanol to yield colourless prisms of (I).
All H atoms were positioned at calculated positions C—H = 0.93Å for aromatic H and C—H = 0.96Å for methyl H and refined using a riding model with Uiso(H) = 1.2Ueq(C)for aromatic and Uiso(H) = 1.2Ueq(C)for for methyl H.
Chalcones are alpha beta unsaturated
widely distributed in nature and are extensively studied for their biological activity (e.g. Chun et al., 2001; Horng et al., 2003; Mei et al., 2003). In this paper we report the of the title chalcone derivative, (I) (Fig. 1).The
contains eight molecules. The five-membered thiophene ring (S2\C19\···C22) is not coplanar with the phenyl ring (C10\C11\···C15) system; the dihedral angle between the two planes is 13.08 (16)°. The displays intermolecular C21—H21···O6 and weak intramolecular C8—H8B···O5 and C9—H9B···O4 hydrogen bonds (Table 1). The packing of molecules in the is depicted in Fig. 2.For general background to
see: Chun et al. (2001); Horng et al. (2003); Mei et al. (2003).Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010); cell
CrysAlis PRO CCD (Oxford Diffraction, 2010); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).C16H15BrO4S | Dx = 1.578 Mg m−3 |
Mr = 383.25 | Melting point: 421 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2833 reflections |
a = 16.8923 (7) Å | θ = 2.4–25.0° |
b = 8.0793 (6) Å | µ = 2.69 mm−1 |
c = 23.6427 (17) Å | T = 293 K |
V = 3226.7 (4) Å3 | Prism, colourless |
Z = 8 | 0.22 × 0.15 × 0.12 mm |
F(000) = 1552 |
Oxford Diffraction Xcalibur diffractometer | 2833 independent reflections |
Radiation source: Mova (Mo) X-ray Source | 1944 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.055 |
Detector resolution: 16.0839 pixels mm-1 | θmax = 25.0°, θmin = 2.4° |
ω scans | h = −20→20 |
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010) | k = −9→8 |
Tmin = 0.625, Tmax = 1.000 | l = −28→27 |
17608 measured reflections |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0142P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
2833 reflections | Δρmax = 0.37 e Å−3 |
200 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00037 (6) |
C16H15BrO4S | V = 3226.7 (4) Å3 |
Mr = 383.25 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 16.8923 (7) Å | µ = 2.69 mm−1 |
b = 8.0793 (6) Å | T = 293 K |
c = 23.6427 (17) Å | 0.22 × 0.15 × 0.12 mm |
Oxford Diffraction Xcalibur diffractometer | 2833 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010) | 1944 reflections with I > 2σ(I) |
Tmin = 0.625, Tmax = 1.000 | Rint = 0.055 |
17608 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.074 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.37 e Å−3 |
2833 reflections | Δρmin = −0.30 e Å−3 |
200 parameters |
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. IR (KBr) 1653.9, 1597.8, 1071.2, 811.3 cm-1. 1H-NMR (300 MHz, CDCl3): δ 7.755–7.806 (s, 2 H, Ar–H), 7.114–7.251 (m, 4H, Ar–H and HC=CH), 3.922–3.942 (s, 9 H, OCH3). |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.22995 (2) | 0.12039 (5) | 0.462527 (19) | 0.05957 (17) | |
S2 | 0.40847 (5) | 0.19214 (12) | 0.47450 (4) | 0.0457 (3) | |
O3 | 0.58044 (13) | 0.2459 (3) | 0.47770 (11) | 0.0554 (7) | |
O4 | 0.97395 (13) | 0.0142 (3) | 0.35359 (11) | 0.0548 (7) | |
O5 | 0.93207 (14) | −0.0951 (3) | 0.25109 (10) | 0.0536 (7) | |
O6 | 0.78125 (15) | −0.1434 (3) | 0.22387 (10) | 0.0584 (8) | |
C7 | 0.7010 (2) | −0.1558 (6) | 0.20613 (17) | 0.0786 (15) | |
H7A | 0.6988 | −0.2054 | 0.1693 | 0.118* | |
H7B | 0.6779 | −0.0473 | 0.2047 | 0.118* | |
H7C | 0.6721 | −0.2231 | 0.2325 | 0.118* | |
C8 | 0.9680 (2) | −0.2507 (5) | 0.25738 (19) | 0.0836 (16) | |
H8A | 1.0071 | −0.2655 | 0.2283 | 0.125* | |
H8B | 0.9285 | −0.3358 | 0.2543 | 0.125* | |
H8C | 0.9929 | −0.2572 | 0.2938 | 0.125* | |
C9 | 0.9990 (2) | 0.0853 (5) | 0.40581 (16) | 0.0609 (12) | |
H9A | 1.0557 | 0.0825 | 0.4080 | 0.091* | |
H9B | 0.9770 | 0.0233 | 0.4367 | 0.091* | |
H9C | 0.9811 | 0.1979 | 0.4079 | 0.091* | |
C10 | 0.8948 (2) | 0.0080 (4) | 0.34261 (15) | 0.0413 (9) | |
C11 | 0.8748 (2) | −0.0580 (4) | 0.29009 (14) | 0.0394 (9) | |
C12 | 0.7953 (2) | −0.0746 (5) | 0.27587 (15) | 0.0451 (10) | |
C13 | 0.7371 (2) | −0.0232 (4) | 0.31290 (15) | 0.0433 (10) | |
H13 | 0.6841 | −0.0355 | 0.3031 | 0.052* | |
C14 | 0.7572 (2) | 0.0468 (4) | 0.36467 (15) | 0.0379 (9) | |
C15 | 0.8364 (2) | 0.0618 (4) | 0.37962 (14) | 0.0420 (9) | |
H15 | 0.8502 | 0.1078 | 0.4143 | 0.050* | |
C16 | 0.69605 (19) | 0.1080 (4) | 0.40313 (15) | 0.0426 (9) | |
H16 | 0.7133 | 0.1705 | 0.4338 | 0.051* | |
C17 | 0.61970 (19) | 0.0843 (4) | 0.39899 (14) | 0.0424 (9) | |
H17 | 0.6011 | 0.0188 | 0.3695 | 0.051* | |
C18 | 0.5618 (2) | 0.1556 (4) | 0.43846 (15) | 0.0402 (9) | |
C19 | 0.47821 (19) | 0.1147 (4) | 0.42830 (14) | 0.0364 (9) | |
C20 | 0.4436 (2) | 0.0223 (4) | 0.38785 (14) | 0.0448 (10) | |
H20 | 0.4718 | −0.0289 | 0.3590 | 0.054* | |
C21 | 0.3606 (2) | 0.0105 (4) | 0.39334 (15) | 0.0482 (10) | |
H21 | 0.3281 | −0.0490 | 0.3690 | 0.058* | |
C22 | 0.3348 (2) | 0.0965 (4) | 0.43839 (15) | 0.0418 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0319 (2) | 0.0731 (3) | 0.0738 (3) | 0.0005 (2) | 0.0004 (2) | −0.0001 (3) |
S2 | 0.0331 (5) | 0.0599 (7) | 0.0441 (6) | 0.0009 (5) | 0.0020 (4) | −0.0137 (5) |
O3 | 0.0377 (14) | 0.0760 (19) | 0.0525 (17) | 0.0036 (14) | −0.0002 (13) | −0.0232 (15) |
O4 | 0.0358 (15) | 0.081 (2) | 0.0480 (16) | 0.0026 (14) | 0.0056 (13) | −0.0046 (15) |
O5 | 0.0545 (16) | 0.0651 (18) | 0.0411 (15) | 0.0098 (15) | 0.0226 (14) | 0.0057 (14) |
O6 | 0.0559 (17) | 0.083 (2) | 0.0363 (15) | −0.0106 (16) | 0.0095 (14) | −0.0114 (15) |
C7 | 0.066 (3) | 0.115 (4) | 0.055 (3) | −0.029 (3) | 0.000 (3) | −0.023 (3) |
C8 | 0.089 (4) | 0.075 (4) | 0.086 (4) | 0.025 (3) | 0.039 (3) | 0.003 (3) |
C9 | 0.043 (2) | 0.078 (3) | 0.062 (3) | −0.010 (2) | −0.008 (2) | 0.001 (3) |
C10 | 0.035 (2) | 0.050 (2) | 0.038 (2) | 0.0007 (19) | 0.0063 (18) | 0.0078 (19) |
C11 | 0.042 (2) | 0.043 (2) | 0.033 (2) | 0.0036 (19) | 0.0108 (18) | 0.0094 (18) |
C12 | 0.054 (2) | 0.047 (2) | 0.034 (2) | −0.002 (2) | 0.006 (2) | 0.0072 (19) |
C13 | 0.034 (2) | 0.055 (3) | 0.041 (2) | −0.0011 (19) | 0.0045 (18) | 0.004 (2) |
C14 | 0.037 (2) | 0.040 (2) | 0.037 (2) | 0.0061 (18) | 0.0056 (18) | 0.0036 (18) |
C15 | 0.039 (2) | 0.053 (2) | 0.034 (2) | 0.0055 (19) | 0.0024 (18) | 0.0007 (19) |
C16 | 0.040 (2) | 0.053 (3) | 0.034 (2) | 0.005 (2) | 0.0021 (18) | −0.0043 (19) |
C17 | 0.036 (2) | 0.052 (2) | 0.039 (2) | −0.0002 (19) | 0.0052 (18) | −0.0038 (19) |
C18 | 0.036 (2) | 0.049 (2) | 0.036 (2) | 0.0041 (19) | 0.0008 (18) | 0.0045 (19) |
C19 | 0.0360 (19) | 0.040 (2) | 0.0327 (19) | 0.0027 (18) | 0.0062 (17) | −0.0003 (18) |
C20 | 0.045 (2) | 0.054 (3) | 0.036 (2) | −0.001 (2) | 0.0046 (18) | −0.0100 (19) |
C21 | 0.045 (2) | 0.062 (3) | 0.037 (2) | −0.011 (2) | −0.0103 (19) | −0.006 (2) |
C22 | 0.0327 (19) | 0.047 (2) | 0.045 (2) | −0.0008 (18) | −0.0077 (18) | 0.003 (2) |
Br1—C22 | 1.871 (3) | C10—C15 | 1.389 (4) |
S2—C22 | 1.695 (3) | C10—C11 | 1.393 (5) |
S2—C19 | 1.724 (3) | C11—C12 | 1.390 (5) |
O3—C18 | 1.221 (4) | C12—C13 | 1.381 (5) |
O4—C10 | 1.363 (4) | C13—C14 | 1.390 (5) |
O4—C9 | 1.426 (4) | C13—H13 | 0.9300 |
O5—C11 | 1.370 (4) | C14—C15 | 1.389 (4) |
O5—C8 | 1.404 (4) | C14—C16 | 1.462 (4) |
O6—C12 | 1.370 (4) | C15—H15 | 0.9300 |
O6—C7 | 1.423 (4) | C16—C17 | 1.308 (4) |
C7—H7A | 0.9600 | C16—H16 | 0.9300 |
C7—H7B | 0.9600 | C17—C18 | 1.469 (4) |
C7—H7C | 0.9600 | C17—H17 | 0.9300 |
C8—H8A | 0.9600 | C18—C19 | 1.470 (4) |
C8—H8B | 0.9600 | C19—C20 | 1.347 (4) |
C8—H8C | 0.9600 | C20—C21 | 1.410 (5) |
C9—H9A | 0.9600 | C20—H20 | 0.9300 |
C9—H9B | 0.9600 | C21—C22 | 1.344 (5) |
C9—H9C | 0.9600 | C21—H21 | 0.9300 |
C22—S2—C19 | 90.97 (17) | C12—C13—C14 | 120.5 (3) |
C10—O4—C9 | 118.1 (3) | C12—C13—H13 | 119.7 |
C11—O5—C8 | 115.5 (3) | C14—C13—H13 | 119.7 |
C12—O6—C7 | 117.3 (3) | C15—C14—C13 | 119.6 (3) |
O6—C7—H7A | 109.5 | C15—C14—C16 | 119.5 (3) |
O6—C7—H7B | 109.5 | C13—C14—C16 | 120.9 (3) |
H7A—C7—H7B | 109.5 | C14—C15—C10 | 119.8 (3) |
O6—C7—H7C | 109.5 | C14—C15—H15 | 120.1 |
H7A—C7—H7C | 109.5 | C10—C15—H15 | 120.1 |
H7B—C7—H7C | 109.5 | C17—C16—C14 | 126.9 (4) |
O5—C8—H8A | 109.5 | C17—C16—H16 | 116.6 |
O5—C8—H8B | 109.5 | C14—C16—H16 | 116.6 |
H8A—C8—H8B | 109.5 | C16—C17—C18 | 123.4 (3) |
O5—C8—H8C | 109.5 | C16—C17—H17 | 118.3 |
H8A—C8—H8C | 109.5 | C18—C17—H17 | 118.3 |
H8B—C8—H8C | 109.5 | O3—C18—C17 | 123.1 (3) |
O4—C9—H9A | 109.5 | O3—C18—C19 | 120.4 (3) |
O4—C9—H9B | 109.5 | C17—C18—C19 | 116.6 (3) |
H9A—C9—H9B | 109.5 | C20—C19—C18 | 131.1 (3) |
O4—C9—H9C | 109.5 | C20—C19—S2 | 110.7 (3) |
H9A—C9—H9C | 109.5 | C18—C19—S2 | 118.1 (3) |
H9B—C9—H9C | 109.5 | C19—C20—C21 | 113.8 (3) |
O4—C10—C15 | 124.5 (3) | C19—C20—H20 | 123.1 |
O4—C10—C11 | 115.0 (3) | C21—C20—H20 | 123.1 |
C15—C10—C11 | 120.6 (3) | C22—C21—C20 | 111.1 (3) |
O5—C11—C12 | 119.9 (3) | C22—C21—H21 | 124.4 |
O5—C11—C10 | 120.8 (3) | C20—C21—H21 | 124.4 |
C12—C11—C10 | 119.2 (3) | C21—C22—S2 | 113.3 (3) |
O6—C12—C13 | 124.6 (4) | C21—C22—Br1 | 127.0 (3) |
O6—C12—C11 | 115.1 (3) | S2—C22—Br1 | 119.6 (2) |
C13—C12—C11 | 120.3 (4) | ||
C9—O4—C10—C15 | −2.0 (5) | O4—C10—C15—C14 | −178.7 (3) |
C9—O4—C10—C11 | 178.0 (3) | C11—C10—C15—C14 | 1.3 (5) |
C8—O5—C11—C12 | −100.4 (4) | C15—C14—C16—C17 | −170.3 (4) |
C8—O5—C11—C10 | 84.3 (4) | C13—C14—C16—C17 | 10.9 (6) |
O4—C10—C11—O5 | −6.9 (5) | C14—C16—C17—C18 | −177.6 (3) |
C15—C10—C11—O5 | 173.1 (3) | C16—C17—C18—O3 | 1.6 (6) |
O4—C10—C11—C12 | 177.8 (3) | C16—C17—C18—C19 | −179.1 (3) |
C15—C10—C11—C12 | −2.2 (5) | O3—C18—C19—C20 | 178.5 (4) |
C7—O6—C12—C13 | 2.8 (5) | C17—C18—C19—C20 | −0.8 (6) |
C7—O6—C12—C11 | −177.0 (3) | O3—C18—C19—S2 | −2.1 (5) |
O5—C11—C12—O6 | 5.8 (5) | C17—C18—C19—S2 | 178.6 (2) |
C10—C11—C12—O6 | −178.8 (3) | C22—S2—C19—C20 | 0.5 (3) |
O5—C11—C12—C13 | −174.0 (3) | C22—S2—C19—C18 | −179.1 (3) |
C10—C11—C12—C13 | 1.3 (5) | C18—C19—C20—C21 | 178.9 (3) |
O6—C12—C13—C14 | −179.4 (3) | S2—C19—C20—C21 | −0.5 (4) |
C11—C12—C13—C14 | 0.4 (6) | C19—C20—C21—C22 | 0.3 (5) |
C12—C13—C14—C15 | −1.4 (5) | C20—C21—C22—S2 | 0.1 (4) |
C12—C13—C14—C16 | 177.4 (3) | C20—C21—C22—Br1 | 179.2 (3) |
C13—C14—C15—C10 | 0.5 (5) | C19—S2—C22—C21 | −0.3 (3) |
C16—C14—C15—C10 | −178.3 (3) | C19—S2—C22—Br1 | −179.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O6i | 0.93 | 2.46 | 3.320 (4) | 155 |
Symmetry code: (i) x−1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H15BrO4S |
Mr | 383.25 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 16.8923 (7), 8.0793 (6), 23.6427 (17) |
V (Å3) | 3226.7 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.69 |
Crystal size (mm) | 0.22 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur |
Absorption correction | Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.625, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17608, 2833, 1944 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.074, 0.99 |
No. of reflections | 2833 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.30 |
Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2010), CrysAlis PRO RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O6i | 0.93 | 2.46 | 3.320 (4) | 155 |
Symmetry code: (i) x−1/2, y, −z+1/2. |
Acknowledgements
The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for support of the data collection. SBV thanks the Acharya Nagarjuna University, Gutntur, Andhrapradesh, for support of the part-time PhD programme in Pharmacy.
References
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Chalcones are alpha beta unsaturated ketones, widely distributed in nature and are extensively studied for their biological activity (e.g. Chun et al., 2001; Horng et al., 2003; Mei et al., 2003). In this paper we report the crystal structure of the title chalcone derivative, (I) (Fig. 1).
The unit cell contains eight molecules. The five-membered thiophene ring (S2\C19\···C22) is not coplanar with the phenyl ring (C10\C11\···C15) system; the dihedral angle between the two planes is 13.08 (16)°. The crystal structure displays intermolecular C21—H21···O6 and weak intramolecular C8—H8B···O5 and C9—H9B···O4 hydrogen bonds (Table 1). The packing of molecules in the crystal structure is depicted in Fig. 2.