3-(2-Bromo­acet­yl)phenyl benzoate

Ambekar, S.P.; Devarajegowda, H.C.; ShylajaKumari, J.; Kumar, K.M.; Kotresh, O.

doi:10.1107/S1600536813002900

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o322

doi:10.1107/S1600536813002900

Open

access

3-(2-Bromoacetyl)phenyl benzoate

Sachin P Ambekar,^a H. C. Devarajegowda,^b ^* J. ShylajaKumari,^c K. Mahesh Kumar ^a and O. Kotresh ^a

^aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, ^bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and ^cDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India
^*Correspondence e-mail: devarajegowda@yahoo.com

(Received 24 January 2013; accepted 28 January 2013; online 2 February 2013)

In the title compound, C₁₅H₁₁BrO₃, the dihedral angle between the benzene rings is 72.59 (6)°. In the crystal, pairs of C—H⋯π contacts form inversion dimers. Additional C—H⋯O hydrogen bonds generate R₂¹(6) ring motifs and stack these dimers along the b axis. Short intermolecular Br⋯O contacts of 3.254 (3) Å are also observed and link the stacks into a three-dimensional network.

Related literature

For the biological applications and synthesis of the title compound, see: Naoto et al. (2008 ); Shwu-Jiuan & Mei-Hua (1984 ); Jaakko & Erkki (1959 ); Junichi et al. (1956 ); D'Amico et al. (1956 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 )

Experimental

Crystal data

C₁₅H₁₁BrO₃
M_r = 319.15
Monoclinic, P 2₁ /n
a = 12.5055 (4) Å
b = 5.4409 (2) Å
c = 19.5178 (6) Å
β = 90.859 (2)°
V = 1327.86 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.10 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.770, T_max = 1.000
11209 measured reflections
2344 independent reflections
1929 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.092
S = 1.05
2344 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3ⁱ	0.93	2.70	3.557 (4)	153
C1—H1B⋯O3ⁱ	0.97	2.65	3.550 (4)	155
C6—H6⋯Cg2ⁱⁱ	0.93	2.88	3.627 (3)	138
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813002900/sj5298sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002900/sj5298Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002900/sj5298Isup3.cml

checkCIF report

Comment top

3-(2-bromoacetyl)phenyl benzoate is key starting material for the synthesis of phenylephrine, (R)-3-[-1-hydroxy-2-(methylamino)ethyl]phenol. Phenylephrine is a selective α₁-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupils, and to increase blood pressure.

Oral phenylephrine is extensively metabolized by monoamine oxidase (Naoto et al., 2008), an enzyme that is present in the gastrointestinal tract and in the liver. Therefore, compared to intravenous pseudoephedrine, it has a reduced and variable bioavailability, only up to 38% (Shwu-Jiuan & Mei-Hua, 1984; Jaakko & Erkki, 1959). Because phenylephrine is a directly selective α-adrenergic receptor agonist, it does not cause the release of endogenous noradrenaline, as pseudoephedrine does. Therefore, phenylephrine is less likely to cause side effects such as central nervous system stimulation, insomnia, anxiety, irritability, and restlessness (Junichi et al., 1956). Phenylephrine's effectiveness as a decongestant stems from its vasoconstriction of nasal blood vessels, thereby decreasing blood flow to the sinusoidal vessels, leading to decreased mucosal edema (D'Amico et al., 1956).

The asymmetric unit of 3-(2-bromoacetylphenyl benzoate is shown in Fig. 1. The dihedral angle between two (C3–C8) and (C10—C15) benzene rings is 72.59 (6)°. In the crystal structure a pair of C6—H6···π [C_g(2)(C10–C15) contacts form inversion dimers. Additional C4—H4···O3 and C1—H1B···O3 (Table.1) hydrogen bonds generate R¹₂(6) ring motifs (Bernstein et al., 1995) and stack these dimers along the b axis (Fig. 2). Short intermolecular Br1···O2 contacts, 3.254 (3) Å are also observed and link the stacks into a three dimensional network.

Related literature top

For the biological applications and synthesis of the title compound, see: Naoto et al. (2008); Shwu-Jiuan & Mei-Hua (1984); Jaakko & Erkki (1959); Junichi et al. (1956); D'Amico et al. (1956). For hydrogen-bond motifs, see: Bernstein et al. (1995)

Experimental top

All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to an already reported method (Shwu-Jiuan & Mei-Hua, 1984). The crude product was recrystallized from an ethanol/chloroform mixture, to give colourless crystals in 78% yield.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Crystal packing along b axis for the title compound with hydrogen bonds drawn as dashed lines.

3-(2-Bromoacetyl)phenyl benzoate top

Crystal data top

C₁₅H₁₁BrO₃	F(000) = 640
M_r = 319.15	D_x = 1.596 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 378 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.5055 (4) Å	Cell parameters from 2344 reflections
b = 5.4409 (2) Å	θ = 1.9–25.0°
c = 19.5178 (6) Å	µ = 3.10 mm⁻¹
β = 90.859 (2)°	T = 296 K
V = 1327.86 (8) Å³	Plate, colourless
Z = 4	0.24 × 0.20 × 0.12 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2344 independent reflections
Radiation source: fine-focus sealed tube	1929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω and ϕ scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −14→14
T_min = 0.770, T_max = 1.000	k = −6→6
11209 measured reflections	l = −23→23

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) = 0.092	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0489P)² + 0.8292P] where P = (F_o² + 2F_c²)/3
2344 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₁₅H₁₁BrO₃	V = 1327.86 (8) Å³
M_r = 319.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.5055 (4) Å	µ = 3.10 mm⁻¹
b = 5.4409 (2) Å	T = 296 K
c = 19.5178 (6) Å	0.24 × 0.20 × 0.12 mm
β = 90.859 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2344 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1929 reflections with I > 2σ(I)
T_min = 0.770, T_max = 1.000	R_int = 0.033
11209 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
2344 reflections	Δρ_min = −0.62 e Å⁻³
172 parameters

Special details top

Experimental. 3-(Bromo acetyl) phenyl benzoate: it was obtained as an off-white solid; M.P: 378k; GCMS data m/e 320 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 4.46 (s 2H, Methylene-CH₂),7.50 (s,1H, Ar—H), 7.52 (s,1H, Ar—H), 7.66 (s,1H, Ar—H), 7.68 (s,1H, Ar—H), 7.88 (s,1H, Ar—H), 7.90 (s,1H, Ar—H), 8.19 (d,2H, Ar—H),

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	0.93093 (3)	−0.55127 (7)	0.763352 (16)	0.05813 (16)
O1	0.57395 (15)	0.2166 (4)	0.92902 (10)	0.0458 (5)
O2	1.00505 (17)	−0.2020 (5)	0.87494 (14)	0.0697 (7)
O3	0.5845 (2)	0.5101 (5)	0.84970 (16)	0.0724 (8)
C1	0.8494 (2)	−0.3090 (7)	0.81046 (16)	0.0524 (8)
H1A	0.8210	−0.1928	0.7772	0.063*
H1B	0.7893	−0.3891	0.8319	0.063*
C2	0.9115 (2)	−0.1696 (6)	0.86438 (15)	0.0410 (7)
C3	0.8497 (2)	0.0154 (5)	0.90374 (14)	0.0371 (7)
C4	0.7386 (2)	0.0330 (6)	0.89847 (14)	0.0378 (6)
H4	0.7002	−0.0766	0.8710	0.045*
C5	0.6866 (2)	0.2118 (6)	0.93378 (14)	0.0396 (7)
C6	0.7396 (3)	0.3758 (6)	0.97553 (16)	0.0489 (8)
H6	0.7025	0.4965	0.9991	0.059*
C7	0.8502 (3)	0.3567 (7)	0.98166 (16)	0.0519 (8)
H7	0.8878	0.4647	1.0100	0.062*
C8	0.9040 (2)	0.1796 (6)	0.94613 (14)	0.0438 (7)
H8	0.9780	0.1693	0.9505	0.053*
C9	0.5314 (2)	0.3695 (6)	0.88120 (16)	0.0430 (7)
C10	0.4140 (2)	0.3355 (6)	0.87324 (15)	0.0392 (7)
C11	0.3575 (3)	0.5030 (6)	0.83355 (19)	0.0564 (9)
H11	0.3929	0.6327	0.8127	0.068*
C12	0.2485 (3)	0.4773 (7)	0.8249 (2)	0.0626 (10)
H12	0.2102	0.5922	0.7992	0.075*
C13	0.1965 (3)	0.2843 (7)	0.85389 (17)	0.0553 (9)
H13	0.1231	0.2664	0.8473	0.066*
C14	0.2517 (3)	0.1179 (7)	0.89246 (18)	0.0546 (9)
H14	0.2158	−0.0137	0.9120	0.066*
C15	0.3611 (2)	0.1427 (6)	0.90285 (16)	0.0476 (7)
H15	0.3984	0.0294	0.9297	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0559 (2)	0.0682 (3)	0.0502 (2)	0.01670 (17)	−0.00215 (15)	−0.00925 (17)
O1	0.0314 (10)	0.0549 (13)	0.0512 (12)	0.0049 (10)	0.0054 (9)	0.0110 (10)
O2	0.0332 (13)	0.0820 (19)	0.0935 (18)	0.0101 (12)	−0.0161 (11)	−0.0277 (15)
O3	0.0443 (13)	0.0693 (17)	0.103 (2)	−0.0134 (12)	−0.0088 (13)	0.0430 (16)
C1	0.0366 (16)	0.069 (2)	0.0517 (17)	0.0138 (16)	−0.0050 (13)	−0.0151 (17)
C2	0.0282 (15)	0.0483 (18)	0.0463 (16)	−0.0014 (13)	−0.0045 (12)	0.0000 (15)
C3	0.0308 (14)	0.0420 (17)	0.0384 (15)	−0.0019 (12)	−0.0043 (12)	0.0032 (12)
C4	0.0319 (14)	0.0423 (16)	0.0391 (15)	−0.0034 (13)	−0.0045 (12)	0.0002 (13)
C5	0.0318 (14)	0.0472 (18)	0.0400 (15)	0.0001 (13)	0.0014 (12)	0.0079 (14)
C6	0.055 (2)	0.0480 (18)	0.0440 (17)	0.0006 (16)	0.0034 (14)	−0.0049 (15)
C7	0.054 (2)	0.055 (2)	0.0466 (17)	−0.0136 (17)	−0.0107 (14)	−0.0067 (16)
C8	0.0349 (15)	0.0523 (19)	0.0440 (16)	−0.0076 (14)	−0.0085 (13)	0.0005 (15)
C9	0.0398 (16)	0.0384 (16)	0.0510 (17)	0.0032 (14)	0.0036 (14)	0.0030 (15)
C10	0.0353 (15)	0.0350 (16)	0.0474 (16)	0.0028 (13)	0.0029 (12)	−0.0009 (14)
C11	0.0446 (18)	0.054 (2)	0.071 (2)	0.0005 (16)	0.0005 (16)	0.0201 (18)
C12	0.049 (2)	0.067 (2)	0.071 (2)	0.0112 (18)	−0.0079 (17)	0.0168 (19)
C13	0.0350 (16)	0.067 (2)	0.064 (2)	0.0000 (16)	−0.0008 (15)	0.0002 (19)
C14	0.0405 (18)	0.054 (2)	0.069 (2)	−0.0080 (16)	0.0076 (15)	0.0077 (18)
C15	0.0416 (17)	0.0445 (18)	0.0568 (18)	0.0030 (15)	0.0028 (14)	0.0060 (16)

Geometric parameters (Å, º) top

Br1—C1	1.910 (3)	C7—C8	1.370 (5)
O1—C9	1.353 (4)	C7—H7	0.9300
O1—C5	1.411 (3)	C8—H8	0.9300
O2—C2	1.198 (3)	C9—C10	1.485 (4)
O3—C9	1.191 (4)	C10—C15	1.372 (4)
C1—C2	1.503 (4)	C10—C11	1.384 (4)
C1—H1A	0.9700	C11—C12	1.378 (5)
C1—H1B	0.9700	C11—H11	0.9300
C2—C3	1.489 (4)	C12—C13	1.362 (5)
C3—C8	1.388 (4)	C12—H12	0.9300
C3—C4	1.395 (4)	C13—C14	1.359 (5)
C4—C5	1.363 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.387 (4)
C5—C6	1.372 (4)	C14—H14	0.9300
C6—C7	1.390 (4)	C15—H15	0.9300
C6—H6	0.9300

C9—O1—C5	116.0 (2)	C7—C8—C3	121.0 (3)
C2—C1—Br1	114.3 (2)	C7—C8—H8	119.5
C2—C1—H1A	108.7	C3—C8—H8	119.5
Br1—C1—H1A	108.7	O3—C9—O1	122.3 (3)
C2—C1—H1B	108.7	O3—C9—C10	125.8 (3)
Br1—C1—H1B	108.7	O1—C9—C10	111.9 (3)
H1A—C1—H1B	107.6	C15—C10—C11	119.6 (3)
O2—C2—C3	121.6 (3)	C15—C10—C9	122.2 (3)
O2—C2—C1	122.6 (3)	C11—C10—C9	118.2 (3)
C3—C2—C1	115.8 (2)	C12—C11—C10	119.8 (3)
C8—C3—C4	118.5 (3)	C12—C11—H11	120.1
C8—C3—C2	119.3 (3)	C10—C11—H11	120.1
C4—C3—C2	122.2 (3)	C13—C12—C11	120.4 (3)
C5—C4—C3	119.6 (3)	C13—C12—H12	119.8
C5—C4—H4	120.2	C11—C12—H12	119.8
C3—C4—H4	120.2	C14—C13—C12	120.1 (3)
C4—C5—C6	122.4 (3)	C14—C13—H13	120.0
C4—C5—O1	117.6 (3)	C12—C13—H13	120.0
C6—C5—O1	120.0 (3)	C13—C14—C15	120.5 (3)
C5—C6—C7	118.3 (3)	C13—C14—H14	119.7
C5—C6—H6	120.9	C15—C14—H14	119.7
C7—C6—H6	120.9	C10—C15—C14	119.6 (3)
C8—C7—C6	120.3 (3)	C10—C15—H15	120.2
C8—C7—H7	119.8	C14—C15—H15	120.2
C6—C7—H7	119.8

Br1—C1—C2—O2	2.7 (5)	C4—C3—C8—C7	−0.6 (4)
Br1—C1—C2—C3	−178.1 (2)	C2—C3—C8—C7	178.2 (3)
O2—C2—C3—C8	9.9 (5)	C5—O1—C9—O3	−7.3 (5)
C1—C2—C3—C8	−169.3 (3)	C5—O1—C9—C10	171.8 (2)
O2—C2—C3—C4	−171.4 (3)	O3—C9—C10—C15	168.8 (3)
C1—C2—C3—C4	9.4 (4)	O1—C9—C10—C15	−10.3 (4)
C8—C3—C4—C5	1.1 (4)	O3—C9—C10—C11	−10.1 (5)
C2—C3—C4—C5	−177.6 (3)	O1—C9—C10—C11	170.8 (3)
C3—C4—C5—C6	−0.8 (4)	C15—C10—C11—C12	1.0 (5)
C3—C4—C5—O1	−177.6 (2)	C9—C10—C11—C12	179.9 (3)
C9—O1—C5—C4	−95.2 (3)	C10—C11—C12—C13	−1.6 (6)
C9—O1—C5—C6	87.9 (3)	C11—C12—C13—C14	1.1 (6)
C4—C5—C6—C7	−0.1 (5)	C12—C13—C14—C15	0.1 (6)
O1—C5—C6—C7	176.6 (3)	C11—C10—C15—C14	0.2 (5)
C5—C6—C7—C8	0.7 (5)	C9—C10—C15—C14	−178.7 (3)
C6—C7—C8—C3	−0.3 (5)	C13—C14—C15—C10	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.70	3.557 (4)	153
C1—H1B···O3ⁱ	0.97	2.65	3.550 (4)	155
C6—H6···Cg2ⁱⁱ	0.93	2.88	3.627 (3)	138

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁BrO₃
M_r	319.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	12.5055 (4), 5.4409 (2), 19.5178 (6)
β (°)	90.859 (2)
V (Å³)	1327.86 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.10
Crystal size (mm)	0.24 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.770, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11209, 2344, 1929
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.092, 1.05
No. of reflections	2344
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.62

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C10–C15 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.702	3.557 (4)	153
C1—H1B···O3ⁱ	0.97	2.646	3.550 (4)	155
C6—H6···Cg2ⁱⁱ	0.93	2.88	3.627 (3)	138

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

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection and GCMS, IR, CHNS and NMR data. SPA is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
D'Amico, A., Bertolini, L. & Monreale, C. (1956). Chim. l'Ind. (Milan, Italy), 38, 93–99. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jaakko, H. & Erkki, H. (1959). Acta Chem. Scand. 13, 329–33. Google Scholar
Junichi, I., Takuro, I., Chikara, K. & Mitsutaka, K. (1956). Ann. Rept. G. Tanabe Co. Ltd, 1, 17–20. Google Scholar
Naoto, O., Mariko, O., Takashi, S., Satoshi, K., Atsuko, M., Noriaki, U., Yoshisuke, N., Keishi, K., Masamori, S. & Yushi, K. (2008). PCT Int. Appl. WO 2008029825/A1 20080313. Google Scholar
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shwu-Jiuan, L. & Mei-Hua, L. (1984). Bull. Inst. Chem. Acad. Sin. 31, 55–58. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o322

doi:10.1107/S1600536813002900

Open

access