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

Sunitha, K.; Devarajegowda, H.C.; Al-eryani, W.F.A.; Prasad, Y.R.; Kumar, A.U.M.

doi:10.1107/S1600536811052202

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o61

doi:10.1107/S1600536811052202

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

K. Sunitha,^a H. C. Devarajegowda,^b ^* Waleed Fadl Ali Al-eryani,^b Y. Rajendra Prasad ^c and A. Uma Mahesh Kumar ^a

^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 ^cDepartment of Pharmaceutical Chemistry, AU College of Pharmacy, Andhra University, Visakhapatnam, Andhrapradesh, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 14 November 2011; accepted 3 December 2011; online 10 December 2011)

In the title compound, C₁₆H₁₅BrO₄S, the thiophene ring is not coplanar with the benzene ring; the dihedral angle between the two planes is 11.08 (12)°. The crystal structure is characterized by C—H⋯O interactions. Weak intramolecular C—H⋯O hydrogen bonds also occur.

Related literature

For general background to chalcones, see: Chun et al. (2001 ); Horng et al. (2003 ); Lopez et al. (2001 ); Zubieta et al. (2001 ); Howard et al. (2004 ); Petrash (2004 ); Lu et al. (2010 ). Mei et al. (2003 ). For related structures, see: Liang et al. (2011); Alex et al. (1993 ); Li & Su (1993 ).

Experimental

Crystal data

C₁₆H₁₅BrO₄S
M_r = 383.25
Monoclinic, P 2₁ /c
a = 8.114 (5) Å
b = 12.775 (5) Å
c = 15.404 (5) Å
β = 98.813 (5)°
V = 1577.9 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.75 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.228, T_max = 1.000
16471 measured reflections
2784 independent reflections
2343 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.082
S = 1.06
2784 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O5	0.96	2.23	2.861 (4)	122
C9—H9B⋯O4	0.96	2.38	2.985 (4)	120
C21—H21⋯O6ⁱ	0.93	2.41	3.322 (4)	165
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811052202/zj2039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052202/zj2039Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052202/zj2039Isup3.cml

checkCIF report

Comment top

Chalcones are alpha, beta unsaturated ketones, widely distributed in nature and are extensively studied for their biological activity (Chun et al., 2001; Horng et al., 2003; Lopez et al., 2001; Mei et al., 2003). Chalcones readily crystallize because of their intermolecular hydrogen bonding (Liang et al., 2011; Alex et al., 1993; Li et al., 1993). The same property has been shown to be responsible for its biological activity (Zubieta et al., 2001). However, halogen containing chalcones are of special interest in drug design process because of the raising importance of hlogen bond contribution in target recognition process (Howard et al., 2004; Petrash, 2004; Lu et al., 2010). Crystal structure conformation of small molecule has always been the choice for binding energy calculations in docking studies. In this paper we report the crystal structure of (2E)-1-(5-bromothiophen-2-yl)- 3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one which is a part of insilico lead identification studies.

The asymmetric unit of (2E)-1-(5-bromothiophen-2-yl)-3-(2,3,4- trimethoxyphenyl)prop-2-en-1-one, C₁₆H₁₅Br_O4_S, contains just one molecule (Fig. 1). 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 11.08 (12)°. 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.

Related literature top

For general background to chalcones, see: Chun et al. (2001); Horng et al. (2003); Lopez et al. (2001); Zubieta et al. (2001); Howard et al. (2004); Petrash (2004); Lu et al. (2010). Mei et al. (2003). For related structures, see: Liang et al. (2011); Alex et al. (1993); Li et al. (1993).

Experimental top

A mixture of 2-acetyl-5-BromoThiophene (0.01 mole) and 2,3,4- 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.

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010); cell refinement: 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).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The H atoms are shown as spheres of arbitrary radii. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. Packing of the molecules.

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

Crystal data top

C₁₆H₁₅BrO₄S	F(000) = 776
M_r = 383.25	D_x = 1.613 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 400 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.114 (5) Å	Cell parameters from 2784 reflections
b = 12.775 (5) Å	θ = 2.5–25.0°
c = 15.404 (5) Å	µ = 2.75 mm⁻¹
β = 98.813 (5)°	T = 293 K
V = 1577.9 (13) Å³	Prism, colourless
Z = 4	0.22 × 0.15 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2784 independent reflections
Radiation source: fine-focus sealed tube	2343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 16.0839 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	k = −15→15
T_min = 0.228, T_max = 1.000	l = −18→18
16471 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0349P)² + 0.9331P] where P = (F_o² + 2F_c²)/3
2784 reflections	(Δ/σ)_max = 0.007
199 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₆H₁₅BrO₄S	V = 1577.9 (13) Å³
M_r = 383.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.114 (5) Å	µ = 2.75 mm⁻¹
b = 12.775 (5) Å	T = 293 K
c = 15.404 (5) Å	0.22 × 0.15 × 0.12 mm
β = 98.813 (5)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2784 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)	2343 reflections with I > 2σ(I)
T_min = 0.228, T_max = 1.000	R_int = 0.042
16471 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
2784 reflections	Δρ_min = −0.59 e Å⁻³
199 parameters

Special details top

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.24507 (4)	0.00703 (2)	0.22076 (2)	0.05109 (14)
S2	−0.11145 (9)	0.10763 (6)	0.06120 (5)	0.03737 (19)
O3	0.3504 (3)	0.47747 (15)	−0.20529 (13)	0.0450 (5)
O4	0.5493 (2)	0.65241 (14)	−0.19864 (12)	0.0378 (5)
O5	0.5662 (2)	0.78703 (15)	−0.06147 (13)	0.0429 (5)
O6	0.0059 (3)	0.22557 (18)	−0.08036 (14)	0.0561 (6)
C7	0.5915 (4)	0.8532 (3)	0.0134 (2)	0.0527 (8)
H7A	0.6611	0.9111	0.0026	0.079*
H7B	0.6446	0.8143	0.0633	0.079*
H7C	0.4859	0.8790	0.0250	0.079*
C8	0.5199 (4)	0.7480 (2)	−0.2465 (2)	0.0566 (9)
H8A	0.5915	0.7515	−0.2906	0.085*
H8B	0.5428	0.8062	−0.2070	0.085*
H8C	0.4056	0.7507	−0.2742	0.085*
C9	0.2743 (4)	0.5175 (3)	−0.2882 (2)	0.0592 (10)
H9A	0.2735	0.4642	−0.3322	0.089*
H9B	0.3363	0.5769	−0.3036	0.089*
H9C	0.1619	0.5383	−0.2847	0.089*
C10	0.3613 (3)	0.5446 (2)	−0.13548 (17)	0.0301 (6)
C11	0.4561 (3)	0.6350 (2)	−0.13228 (17)	0.0294 (6)
C12	0.4695 (3)	0.6998 (2)	−0.05918 (17)	0.0305 (6)
C13	0.3899 (3)	0.6724 (2)	0.01106 (17)	0.0351 (6)
H13	0.3962	0.7162	0.0597	0.042*
C14	0.3017 (3)	0.5805 (2)	0.00854 (18)	0.0340 (6)
H14	0.2531	0.5616	0.0571	0.041*
C15	0.2827 (3)	0.5150 (2)	−0.06390 (18)	0.0305 (6)
C16	0.1893 (3)	0.4176 (2)	−0.06729 (19)	0.0358 (6)
H16	0.1706	0.3834	−0.1212	0.043*
C17	0.1279 (3)	0.3722 (2)	−0.00165 (19)	0.0387 (7)
H17	0.1416	0.4057	0.0526	0.046*
C18	0.0399 (3)	0.2720 (2)	−0.01058 (19)	0.0368 (7)
C19	−0.0079 (3)	0.2265 (2)	0.06962 (18)	0.0331 (6)
C20	0.0083 (3)	0.2636 (2)	0.15283 (19)	0.0401 (7)
H20	0.0614	0.3264	0.1700	0.048*
C21	−0.0624 (4)	0.1988 (2)	0.21091 (19)	0.0419 (7)
H21	−0.0613	0.2134	0.2702	0.050*
C22	−0.1317 (3)	0.1132 (2)	0.16997 (18)	0.0363 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0619 (2)	0.0412 (2)	0.0540 (2)	−0.00626 (15)	0.02110 (16)	0.01379 (15)
S2	0.0458 (4)	0.0314 (4)	0.0354 (4)	−0.0079 (3)	0.0077 (3)	0.0008 (3)
O3	0.0683 (14)	0.0315 (11)	0.0382 (12)	−0.0042 (10)	0.0176 (10)	−0.0070 (9)
O4	0.0486 (11)	0.0292 (11)	0.0407 (11)	−0.0010 (9)	0.0227 (9)	0.0033 (9)
O5	0.0549 (12)	0.0330 (12)	0.0421 (12)	−0.0122 (9)	0.0114 (9)	−0.0037 (9)
O6	0.0809 (16)	0.0551 (15)	0.0335 (12)	−0.0242 (12)	0.0124 (11)	0.0002 (11)
C7	0.059 (2)	0.0403 (19)	0.060 (2)	−0.0117 (16)	0.0121 (16)	−0.0162 (16)
C8	0.087 (3)	0.043 (2)	0.0442 (19)	−0.0002 (18)	0.0262 (18)	0.0127 (16)
C9	0.065 (2)	0.065 (2)	0.044 (2)	−0.0103 (18)	0.0000 (17)	−0.0121 (17)
C10	0.0364 (14)	0.0231 (14)	0.0320 (15)	0.0040 (11)	0.0093 (11)	0.0001 (11)
C11	0.0346 (14)	0.0260 (14)	0.0292 (14)	0.0040 (11)	0.0103 (11)	0.0053 (11)
C12	0.0336 (14)	0.0247 (14)	0.0333 (15)	0.0009 (11)	0.0058 (11)	0.0031 (12)
C13	0.0430 (16)	0.0350 (16)	0.0272 (14)	0.0009 (13)	0.0056 (12)	−0.0046 (12)
C14	0.0360 (15)	0.0367 (16)	0.0310 (15)	0.0009 (12)	0.0109 (11)	0.0057 (12)
C15	0.0296 (14)	0.0287 (15)	0.0340 (15)	0.0026 (11)	0.0073 (11)	0.0053 (12)
C16	0.0370 (15)	0.0327 (16)	0.0377 (16)	−0.0007 (12)	0.0061 (12)	0.0048 (13)
C17	0.0424 (16)	0.0383 (17)	0.0364 (16)	−0.0056 (13)	0.0093 (13)	0.0036 (13)
C18	0.0367 (15)	0.0373 (17)	0.0369 (17)	−0.0042 (12)	0.0070 (12)	0.0062 (13)
C19	0.0331 (14)	0.0303 (15)	0.0355 (16)	−0.0037 (11)	0.0036 (11)	0.0041 (12)
C20	0.0444 (16)	0.0334 (16)	0.0419 (18)	−0.0105 (13)	0.0043 (13)	−0.0023 (13)
C21	0.0514 (18)	0.0434 (18)	0.0319 (16)	−0.0024 (14)	0.0094 (13)	0.0016 (14)
C22	0.0383 (15)	0.0337 (16)	0.0386 (16)	0.0015 (12)	0.0113 (12)	0.0071 (13)

Geometric parameters (Å, º) top

Br1—C22	1.876 (3)	C10—C11	1.384 (4)
S2—C22	1.710 (3)	C10—C15	1.407 (4)
S2—C19	1.730 (3)	C11—C12	1.388 (4)
O3—C10	1.368 (3)	C12—C13	1.387 (4)
O3—C9	1.426 (4)	C13—C14	1.372 (4)
O4—C11	1.379 (3)	C13—H13	0.9300
O4—C8	1.428 (3)	C14—C15	1.384 (4)
O5—C12	1.366 (3)	C14—H14	0.9300
O5—C7	1.419 (3)	C15—C16	1.454 (4)
O6—C18	1.222 (3)	C16—C17	1.327 (4)
C7—H7A	0.9600	C16—H16	0.9300
C7—H7B	0.9600	C17—C18	1.462 (4)
C7—H7C	0.9600	C17—H17	0.9300
C8—H8A	0.9600	C18—C19	1.470 (4)
C8—H8B	0.9600	C19—C20	1.354 (4)
C8—H8C	0.9600	C20—C21	1.404 (4)
C9—H9A	0.9600	C20—H20	0.9300
C9—H9B	0.9600	C21—C22	1.342 (4)
C9—H9C	0.9600	C21—H21	0.9300

C22—S2—C19	90.49 (13)	C14—C13—C12	119.8 (3)
C10—O3—C9	116.5 (2)	C14—C13—H13	120.1
C11—O4—C8	117.0 (2)	C12—C13—H13	120.1
C12—O5—C7	118.5 (2)	C13—C14—C15	122.2 (2)
O5—C7—H7A	109.5	C13—C14—H14	118.9
O5—C7—H7B	109.5	C15—C14—H14	118.9
H7A—C7—H7B	109.5	C14—C15—C10	117.5 (2)
O5—C7—H7C	109.5	C14—C15—C16	122.6 (2)
H7A—C7—H7C	109.5	C10—C15—C16	119.9 (2)
H7B—C7—H7C	109.5	C17—C16—C15	126.9 (3)
O4—C8—H8A	109.5	C17—C16—H16	116.5
O4—C8—H8B	109.5	C15—C16—H16	116.5
H8A—C8—H8B	109.5	C16—C17—C18	123.1 (3)
O4—C8—H8C	109.5	C16—C17—H17	118.5
H8A—C8—H8C	109.5	C18—C17—H17	118.5
H8B—C8—H8C	109.5	O6—C18—C17	123.3 (3)
O3—C9—H9A	109.5	O6—C18—C19	119.6 (3)
O3—C9—H9B	109.5	C17—C18—C19	117.1 (3)
H9A—C9—H9B	109.5	C20—C19—C18	131.0 (3)
O3—C9—H9C	109.5	C20—C19—S2	110.7 (2)
H9A—C9—H9C	109.5	C18—C19—S2	118.2 (2)
H9B—C9—H9C	109.5	C19—C20—C21	114.0 (3)
O3—C10—C11	121.3 (2)	C19—C20—H20	123.0
O3—C10—C15	117.7 (2)	C21—C20—H20	123.0
C11—C10—C15	120.8 (2)	C22—C21—C20	111.3 (3)
O4—C11—C10	118.2 (2)	C22—C21—H21	124.3
O4—C11—C12	121.4 (2)	C20—C21—H21	124.3
C10—C11—C12	120.0 (2)	C21—C22—S2	113.4 (2)
O5—C12—C13	124.3 (2)	C21—C22—Br1	126.2 (2)
O5—C12—C11	116.1 (2)	S2—C22—Br1	120.36 (16)
C13—C12—C11	119.6 (2)

C9—O3—C10—C11	−63.9 (3)	O3—C10—C15—C16	−2.1 (4)
C9—O3—C10—C15	120.7 (3)	C11—C10—C15—C16	−177.5 (2)
C8—O4—C11—C10	123.4 (3)	C14—C15—C16—C17	−8.3 (4)
C8—O4—C11—C12	−63.4 (3)	C10—C15—C16—C17	170.2 (3)
O3—C10—C11—O4	−4.4 (4)	C15—C16—C17—C18	−178.0 (3)
C15—C10—C11—O4	170.9 (2)	C16—C17—C18—O6	−5.1 (5)
O3—C10—C11—C12	−177.7 (2)	C16—C17—C18—C19	174.6 (3)
C15—C10—C11—C12	−2.5 (4)	O6—C18—C19—C20	−176.7 (3)
C7—O5—C12—C13	1.7 (4)	C17—C18—C19—C20	3.6 (4)
C7—O5—C12—C11	−176.7 (2)	O6—C18—C19—S2	−0.1 (4)
O4—C11—C12—O5	6.6 (4)	C17—C18—C19—S2	−179.73 (19)
C10—C11—C12—O5	179.7 (2)	C22—S2—C19—C20	0.8 (2)
O4—C11—C12—C13	−172.0 (2)	C22—S2—C19—C18	−176.6 (2)
C10—C11—C12—C13	1.2 (4)	C18—C19—C20—C21	176.4 (3)
O5—C12—C13—C14	−177.0 (2)	S2—C19—C20—C21	−0.5 (3)
C11—C12—C13—C14	1.4 (4)	C19—C20—C21—C22	−0.2 (4)
C12—C13—C14—C15	−2.8 (4)	C20—C21—C22—S2	0.8 (3)
C13—C14—C15—C10	1.5 (4)	C20—C21—C22—Br1	−178.3 (2)
C13—C14—C15—C16	−179.9 (2)	C19—S2—C22—C21	−0.9 (2)
O3—C10—C15—C14	176.5 (2)	C19—S2—C22—Br1	178.24 (17)
C11—C10—C15—C14	1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O5	0.96	2.23	2.861 (4)	122
C9—H9B···O4	0.96	2.38	2.985 (4)	120
C21—H21···O6ⁱ	0.93	2.41	3.322 (4)	165

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅BrO₄S
M_r	383.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.114 (5), 12.775 (5), 15.404 (5)
β (°)	98.813 (5)
V (Å³)	1577.9 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.75
Crystal size (mm)	0.22 × 0.15 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)
T_min, T_max	0.228, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16471, 2784, 2343
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.082, 1.06
No. of reflections	2784
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.59

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).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O5	0.96	2.23	2.861 (4)	122.00
C9—H9B···O4	0.96	2.38	2.985 (4)	120.00
C21—H21···O6ⁱ	0.93	2.41	3.322 (4)	165.00

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for support of the X-ray data collection. KS thanks the GITAM University, Visakhapatnam, Andhrapradesh, for financial support under a minor reasearch project.

References

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