(2E)-3-(1,3-Benzodioxol-5-yl)-1-(4-bromo­phen­yl)prop-2-en-1-one

Harrison, W.T.A.; Bindya, S.; Yathirajan, H.S.; Sarojini, B.K.; Narayana, B.

doi:10.1107/S1600536806041547

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 11| November 2006| Pages o5293-o5295

https://doi.org/10.1107/S1600536806041547

(2E)-3-(1,3-Benzodioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one

William T. A. Harrison,^a ^* S. Bindya,^b H. S. Yathirajan,^b B. K. Sarojini ^c and B. Narayana ^d

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India, and ^dDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 14 September 2006; accepted 9 October 2006; online 27 October 2006)

In the approximately planar molecule of the title compound, C₁₆H₁₁BrO₃, the dihedral angle between the two benzene rings is 6.61 (18)°. This compound crystallizes in a centrosymmetric space group, so it does not display a second-harmonic generation response.

Comment

Chalcones have important biological (Dimmock et al., 1999 ) and optical properties (Uchida et al., 1998 ). As part of our ongoing studies of these compounds (Harrison et al., 2006 ), the synthesis and structure of the title compound, (I) (Fig. 1), are presented here. Compound (I) is closely related to (E)-3-(1,3-benzodioxol-5-yl)-1-(4-phenyl)-2-propen-1-one, (II) (Yathirajan et al., 2006 ; Yang et al., 2006 ), with an H atom in (II) replaced by the Br atom in (I).

The crystal structure of compound (I) is centrosymmetric (space group P2₁/n), and thus it has no second-harmonic generation (SHG) response (Watson et al., 1993 ). The geometric parameters for (I) fall within their expected ranges (Allen et al., 1987 ). For the C1–C6 benzene ring, the r.m.s. deviation from the mean plane is 0.007 Å [maximum deviation = 0.010 (3) Å for atom C1]. For the enone O1/C7/C8/C9 fragment and the C10–C15 benzene ring, the corresponding values are 0.004 Å [maximum deviation = 0.005 (3) Å for atom C7] and 0.004 Å [maximum deviation = 0.007 (3) Å for atom C13]. The dihedral angles between atoms O1/C7/C8/C9 and the C1 and C10 benzene ring mean planes are 4.6 (3) and 2.4 (3)°, respectively. The dihedral angle between the benzene ring best planes (C1–C6 and C10–C15) in (I) is 6.61 (18)°, which is much less than the corresponding value of 26.89 (5)° in (II) (Yathirajan et al., 2006). Atom C16 in (I) is displaced from the C10–C15 benzene ring mean plane by 0.147 (7) Å.

A PLATON (Spek, 2003 ) analysis of (I) indicated two possible intermolecular C—H⋯O interactions (Table 1) that might help to establish the crystal packing, which results in [110] chains of molecules (Fig. 2). A slightly short Br1⋯O3ⁱ [symmetry code: (i) $[{3\over 2}]$ + x, $[{3\over 2}]$ − y, z − $[{1\over 2}]$ ] contact of 3.237 (3) Å arises, compared with the expected separation of 3.37 Å for these atoms (Bondi, 1964 ).

Any π–π stacking effects in (I) are probably weak. Although equivalent atoms in adjacent molecules in the [100] direction are separated by the a unit-cell dimension of 3.9221 (2) Å, the aromatic ring systems of the molecules are substantially offset (Fig. 3). The packing in (II) is different and results in herring-bone sheets of molecules in space group Pbca, consolidated by possible C—H⋯π interactions (Yang et al., 2006), which might also correlate with the different dihedral angles between the benzne rings in the two structures.

Figure 1
A view of the molecular structure of (I)

, showing 50% probability displacement ellipsoids (arbitrary spheres for H atoms).

Figure 2
A fragment of the packing of (I)

, with the C—H⋯O interactions shown as dashed lines (symmetry codes as in Table 1

Figure 3
A fragment of the packing of (I)

, with the drawing projected on to the best plane of the O1 molecule, showing the offset of the aromatic rings of adjacent molecules stacked in the [100] direction. H atoms have been omitted for clarity. The closest intermolecular contact is 3.460 (5) Å for C7⋯C6ⁱⁱⁱ. [Symmetry code: (iii) x − 1, y, z.]

Experimental

An aqueous solution of potassium hydroxide (5%, 5 ml) was added slowly with stirring to a mixture of piperonal (1.50 g, 0.01 mol) and 4-bromoacetophenone (1.99 g, 0.01 mol) in ethanol (25 ml). The mixture was stirred at room temperature for 12 h. The precipitated solid was filtered off, washed with water and dried, and crystals of (I) were recrystallized from acetone by slow evaporation (yield 78%; m.p. 413–415 K). Analysis, found (calculated for C₁₆H₁₁BrO₃): C 59.91 (58.03%), H 3.26 (3.35%).

Crystal data

C₁₆H₁₁BrO₃
M_r = 331.16
Monoclinic, P 2₁ /n
a = 3.9221 (2) Å
b = 10.9795 (8) Å
c = 29.840 (2) Å
β = 90.299 (4)°
V = 1284.97 (14) Å³
Z = 4
D_x = 1.712 Mg m⁻³
Mo Kα radiation
μ = 3.20 mm⁻¹
T = 120 (2) K
Lath, colourless
0.53 × 0.10 × 0.03 mm

Data collection

Nonius KappaCCD area-detector diffractometer
ω and φ scans
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.282, T_max = 0.910
10550 measured reflections
2886 independent reflections
2176 reflections with I > 2σ(I)
R_int = 0.057
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.104
S = 1.05
2886 reflections
181 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0205P)² + 3.9272P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.95	2.54	3.384 (5)	148
C5—H5⋯O1ⁱⁱ	0.95	2.61	3.336 (5)	134
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

H atoms were positioned geometrically, with C—H = 0.95–0.98 Å, and refined as riding, with U_iso(H) = 1.2U_eq(C).

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997) and SORTAV (Blessing, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536806041547/sf2007sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806041547/sf2007Isup2.hkl

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997) and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(2E)-3-(1,3-Benzodioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₁BrO₃	F(000) = 664
M_r = 331.16	D_x = 1.712 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2533 reflections
a = 3.9221 (2) Å	θ = 2.9–27.5°
b = 10.9795 (8) Å	µ = 3.20 mm⁻¹
c = 29.840 (2) Å	T = 120 K
β = 90.299 (4)°	Lath, colourless
V = 1284.97 (14) Å³	0.53 × 0.10 × 0.03 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	2886 independent reflections
Radiation source: fine-focus sealed tube	2176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω and φ scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −5→5
T_min = 0.282, T_max = 0.910	k = −13→14
10550 measured reflections	l = −38→38

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: none
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0205P)² + 3.9272P] where P = (F_o² + 2F_c²)/3
2886 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

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
C1	0.3310 (10)	0.4388 (4)	0.17536 (13)	0.0216 (9)
H1	0.3885	0.3549	0.1768	0.026*
C2	0.1758 (10)	0.4840 (4)	0.13692 (14)	0.0231 (9)
H2	0.1314	0.4324	0.1120	0.028*
C3	0.0878 (9)	0.6051 (4)	0.13562 (13)	0.0189 (8)
C4	0.1491 (10)	0.6820 (4)	0.17167 (13)	0.0218 (8)
H4	0.0829	0.7652	0.1704	0.026*
C5	0.3091 (10)	0.6355 (4)	0.20971 (14)	0.0214 (9)
H5	0.3539	0.6874	0.2345	0.026*
C6	0.4041 (9)	0.5132 (4)	0.21166 (13)	0.0180 (8)
C7	0.5891 (9)	0.4595 (4)	0.25081 (13)	0.0187 (8)
C8	0.6549 (10)	0.5346 (4)	0.29119 (14)	0.0229 (9)
H8	0.5765	0.6164	0.2922	0.027*
C9	0.8237 (10)	0.4878 (4)	0.32608 (13)	0.0203 (8)
H9	0.9017	0.4064	0.3227	0.024*
C10	0.9034 (9)	0.5462 (4)	0.36885 (13)	0.0191 (8)
C11	0.8019 (10)	0.6677 (4)	0.37820 (13)	0.0217 (8)
H11	0.6803	0.7153	0.3569	0.026*
C12	0.8879 (9)	0.7128 (4)	0.41944 (14)	0.0203 (9)
C13	1.0677 (10)	0.6453 (4)	0.45084 (13)	0.0225 (9)
C14	1.1662 (10)	0.5281 (4)	0.44332 (14)	0.0235 (9)
H14	1.2852	0.4818	0.4653	0.028*
C15	1.0814 (10)	0.4799 (4)	0.40119 (14)	0.0223 (9)
H15	1.1480	0.3988	0.3944	0.027*
C16	0.9960 (11)	0.8330 (4)	0.47829 (14)	0.0286 (10)
H16A	1.1925	0.8887	0.4746	0.034*
H16B	0.8494	0.8652	0.5025	0.034*
O1	0.6843 (7)	0.3529 (2)	0.24915 (10)	0.0263 (7)
O2	0.8060 (7)	0.8252 (3)	0.43716 (9)	0.0277 (7)
O3	1.1131 (8)	0.7136 (3)	0.48956 (10)	0.0299 (7)
Br1	−0.11012 (10)	0.67243 (4)	0.082945 (13)	0.02512 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.027 (2)	0.019 (2)	0.019 (2)	−0.0030 (17)	0.0002 (17)	−0.0016 (17)
C2	0.025 (2)	0.027 (2)	0.017 (2)	−0.0008 (18)	0.0016 (16)	−0.0072 (18)
C3	0.0149 (19)	0.025 (2)	0.016 (2)	−0.0008 (16)	−0.0003 (15)	0.0037 (16)
C4	0.023 (2)	0.024 (2)	0.019 (2)	0.0008 (18)	0.0000 (15)	0.0007 (18)
C5	0.025 (2)	0.022 (2)	0.017 (2)	0.0006 (17)	−0.0046 (16)	−0.0021 (16)
C6	0.0169 (19)	0.019 (2)	0.018 (2)	−0.0016 (16)	0.0010 (15)	−0.0010 (16)
C7	0.0177 (19)	0.022 (2)	0.017 (2)	−0.0025 (16)	0.0052 (15)	0.0028 (16)
C8	0.026 (2)	0.020 (2)	0.022 (2)	−0.0005 (17)	−0.0017 (17)	−0.0004 (17)
C9	0.020 (2)	0.020 (2)	0.021 (2)	0.0000 (16)	0.0015 (16)	−0.0017 (17)
C10	0.018 (2)	0.024 (2)	0.0153 (19)	−0.0047 (16)	0.0010 (15)	0.0040 (16)
C11	0.022 (2)	0.027 (2)	0.0158 (19)	−0.0046 (18)	0.0000 (15)	0.0047 (18)
C12	0.0149 (19)	0.025 (2)	0.021 (2)	−0.0007 (16)	0.0008 (15)	0.0002 (17)
C13	0.023 (2)	0.028 (2)	0.016 (2)	−0.0079 (17)	−0.0021 (16)	0.0028 (17)
C14	0.024 (2)	0.030 (2)	0.016 (2)	−0.0001 (18)	−0.0034 (16)	0.0088 (17)
C15	0.023 (2)	0.021 (2)	0.022 (2)	−0.0001 (17)	−0.0027 (16)	0.0025 (17)
C16	0.032 (2)	0.033 (2)	0.021 (2)	0.003 (2)	−0.0048 (18)	−0.003 (2)
O1	0.0347 (17)	0.0194 (16)	0.0246 (16)	0.0023 (13)	−0.0051 (13)	−0.0013 (13)
O2	0.0392 (17)	0.0239 (15)	0.0198 (15)	0.0040 (14)	−0.0073 (12)	−0.0038 (13)
O3	0.0391 (18)	0.0324 (17)	0.0182 (16)	−0.0005 (14)	−0.0072 (13)	0.0015 (13)
Br1	0.0227 (2)	0.0354 (3)	0.0172 (2)	−0.0005 (2)	−0.00468 (14)	0.0035 (2)

Geometric parameters (Å, º) top

C1—C6	1.385 (5)	C9—H9	0.9500
C1—C2	1.387 (5)	C10—C15	1.393 (5)
C1—H1	0.9500	C10—C11	1.420 (6)
C2—C3	1.374 (6)	C11—C12	1.367 (5)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.388 (5)	C12—O2	1.381 (5)
C3—Br1	1.899 (4)	C12—C13	1.385 (6)
C4—C5	1.391 (5)	C13—C14	1.362 (6)
C4—H4	0.9500	C13—O3	1.388 (5)
C5—C6	1.395 (5)	C14—C15	1.402 (6)
C5—H5	0.9500	C14—H14	0.9500
C6—C7	1.493 (5)	C15—H15	0.9500
C7—O1	1.229 (5)	C16—O3	1.429 (5)
C7—C8	1.482 (6)	C16—O2	1.435 (5)
C8—C9	1.334 (5)	C16—H16A	0.9900
C8—H8	0.9500	C16—H16B	0.9900
C9—C10	1.461 (5)

C6—C1—C2	121.6 (4)	C15—C10—C11	119.6 (4)
C6—C1—H1	119.2	C15—C10—C9	118.7 (4)
C2—C1—H1	119.2	C11—C10—C9	121.7 (4)
C3—C2—C1	118.6 (4)	C12—C11—C10	116.7 (4)
C3—C2—H2	120.7	C12—C11—H11	121.6
C1—C2—H2	120.7	C10—C11—H11	121.6
C2—C3—C4	121.6 (4)	C11—C12—O2	127.7 (4)
C2—C3—Br1	120.1 (3)	C11—C12—C13	122.5 (4)
C4—C3—Br1	118.3 (3)	O2—C12—C13	109.8 (3)
C3—C4—C5	119.0 (4)	C14—C13—C12	122.6 (4)
C3—C4—H4	120.5	C14—C13—O3	127.7 (4)
C5—C4—H4	120.5	C12—C13—O3	109.7 (4)
C4—C5—C6	120.5 (4)	C13—C14—C15	116.0 (4)
C4—C5—H5	119.8	C13—C14—H14	122.0
C6—C5—H5	119.8	C15—C14—H14	122.0
C1—C6—C5	118.7 (4)	C10—C15—C14	122.6 (4)
C1—C6—C7	118.5 (4)	C10—C15—H15	118.7
C5—C6—C7	122.8 (4)	C14—C15—H15	118.7
O1—C7—C8	120.7 (4)	O3—C16—O2	108.1 (3)
O1—C7—C6	119.4 (4)	O3—C16—H16A	110.1
C8—C7—C6	119.9 (3)	O2—C16—H16A	110.1
C9—C8—C7	120.3 (4)	O3—C16—H16B	110.1
C9—C8—H8	119.9	O2—C16—H16B	110.1
C7—C8—H8	119.9	H16A—C16—H16B	108.4
C8—C9—C10	128.0 (4)	C12—O2—C16	105.1 (3)
C8—C9—H9	116.0	C13—O3—C16	105.1 (3)
C10—C9—H9	116.0

C6—C1—C2—C3	−1.3 (6)	C15—C10—C11—C12	0.0 (5)
C1—C2—C3—C4	−0.3 (6)	C9—C10—C11—C12	179.5 (4)
C1—C2—C3—Br1	177.7 (3)	C10—C11—C12—O2	−176.8 (4)
C2—C3—C4—C5	1.1 (6)	C10—C11—C12—C13	0.6 (6)
Br1—C3—C4—C5	−176.9 (3)	C11—C12—C13—C14	−1.3 (6)
C3—C4—C5—C6	−0.4 (6)	O2—C12—C13—C14	176.5 (4)
C2—C1—C6—C5	2.0 (6)	C11—C12—C13—O3	−179.1 (4)
C2—C1—C6—C7	−176.6 (4)	O2—C12—C13—O3	−1.2 (5)
C4—C5—C6—C1	−1.1 (6)	C12—C13—C14—C15	1.4 (6)
C4—C5—C6—C7	177.4 (4)	O3—C13—C14—C15	178.7 (4)
C1—C6—C7—O1	3.1 (5)	C11—C10—C15—C14	0.1 (6)
C5—C6—C7—O1	−175.4 (4)	C9—C10—C15—C14	−179.4 (4)
C1—C6—C7—C8	−176.7 (3)	C13—C14—C15—C10	−0.8 (6)
C5—C6—C7—C8	4.8 (6)	C11—C12—O2—C16	−172.2 (4)
O1—C7—C8—C9	1.1 (6)	C13—C12—O2—C16	10.1 (4)
C6—C7—C8—C9	−179.2 (4)	O3—C16—O2—C12	−15.1 (4)
C7—C8—C9—C10	−178.1 (4)	C14—C13—O3—C16	174.2 (4)
C8—C9—C10—C15	179.4 (4)	C12—C13—O3—C16	−8.2 (4)
C8—C9—C10—C11	−0.1 (6)	O2—C16—O3—C13	14.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.95	2.54	3.384 (5)	148
C5—H5···O1ⁱⁱ	0.95	2.61	3.336 (5)	134

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

Acknowledgements

We thank the EPSRC National Crystallographic Service (University of Southampton) for the data collection. BKS thanks AICTE, Government of India, New Delhi, for financial assistance under the `Career Award for Young Teachers' scheme.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Bondi, A. (1964). J. Phys. Chem. 68, 441–451. CrossRef CAS Web of Science Google Scholar
Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dimmock, J. R., Elias, D. W., Beazley, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harrison, W. T. A., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj, K. K. (2006). Acta Cryst. E62, o1578–o1579. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. & Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140. Web of Science CrossRef Google Scholar
Watson, G. J. R., Turner, A. B. & Allen, S. (1993). Organic Materials for Nonlinear Optics III, edited by G. J. Ashwell & D. Bloor. RSC Special Publication No. 137, pp. 112–117. Cambridge: Royal Society of Chemistry. Google Scholar
Yang, X.-H., Wu, M.-H., Zou, W.-D. & Li, C. (2006). Acta Cryst. E62, o3117–o3118. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yathirajan, H. S., Sarojini, B. K., Narayana, B., Bindya, S. & Bolte, M. (2006). Acta Cryst. E62, o3629–o3630. Web of Science CSD CrossRef IUCr Journals Google Scholar

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