Crystal structure of 4-bromo­phenyl-2-oxo-2H-chromene-3-carboxyl­ate

Devarajegowda, H.C.; Suchetan, P.A.; Srinivasa, H.T.; Sreenivasa, S.; Palakshamurthy, B.S.

doi:10.1107/S2056989015006738

organic compounds

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Volume 71| Part 5| May 2015| Pages o326-o327

https://doi.org/10.1107/S2056989015006738

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Crystal structure of 4-bromophenyl-2-oxo-2H-chromene-3-carboxylate

H. C. Devarajegowda,^a P. A. Suchetan,^b H. T. Srinivasa,^c S. Sreenivasa ^d and B. S. Palakshamurthy ^a ^*

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore, Karnataka 570 005, India, ^bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore, Karnataka 560080, India, and ^dDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: palaksha.bspm@gmail.com

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 13 March 2015; accepted 3 April 2015; online 22 April 2015)

In the title compound, C₁₆H₉BrO₄, the coumarin ring system is approximately planar, with an r.m.s deviation of the ten fitted non-H atoms of 0.031 Å, and forms a dihedral angle of 25.85 (10)° with the bromobenzene ring. The carbonyl atoms are syn. In the crystal, molecules are connected along [001] via C—H⋯O interactions, forming C(6) chains. Neighbouring C(6) chains are connected via several π–π interactions [range of centroid–centroid distances = 3.7254 (15)–3.7716 (16) Å], leading to sheets propagating in the bc plane.

Keywords: crystal structure; 2-oxo-2H-chromene; hydrogen bonding; π–π interactions.

CCDC reference: 1057743

1. Related literature

For related structures, see: Sreenivasa et al. (2013 ); Palakshamurthy, Sreenivasa et al. (2013 ); Palakshamurthy, Devarajegowda et al. (2013 ); Devarajegowda et al. (2013 ). For the biological activity and other applications of 2-oxo-2H-chromene derivatives, see: Abdel-Aziz et al. (2013 ); Kostova (2006 ); Chandrasekharan & Kelly (2002 ).

2. Experimental

2.1. Crystal data

C₁₆H₉BrO₄
M_r = 345.14
Monoclinic, P 2₁ /c
a = 16.0782 (10) Å
b = 7.2618 (4) Å
c = 12.7396 (8) Å
β = 113.311 (4)°
V = 1366.01 (15) Å³
Z = 4
Mo Kα radiation
μ = 3.02 mm⁻¹
T = 296 K
0.24 × 0.18 × 0.16 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.526, T_max = 0.617
20483 measured reflections
2395 independent reflections
1831 reflections with I > 2σ(I)
R_int = 0.037

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.079
S = 1.01
2395 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O3ⁱ	0.93	2.40	3.124 (3)	134
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL2014.

Supporting information

CCDC reference: 1057743

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006738/tk5362sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015006738/tk5362Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015006738/tk5362Isup3.cml

checkCIF report

Chemical context top

Hetero cyclic compounds of 2-oxo-2H-chromenes display wide range of biological activities such as anti-HIV (Kostova, et al., 2006), anti-cancer (Abdel-Aziz et al.,2013), etc. They also play a significant role as chemical sensors, fluorescent probes and laser dyes (Chandrasekharan et al., 2002). In continuation of our work on 2-oxo-2H-chromene derivatives (Sreenivasa et al., 2013; Palakshamurthy, Sreenivasa et al., 2013; Palakshamurthy, Devarajegowda et al., 2013; Devarajegowda, et al.,2013), in the present work we report the synthesis and crystal structure of 4-bromophenyl-2-oxo-2H-chromene-3-carboxylate (I), an intermediate compound obtained during synthesis of coumarin–based Liquid Crystals (LCs).

Structural commentary top

The dihedral angle between the coumarin ring and the bromobenzene ring in (I) is 25.85 (10)°. Compared to this, the dihedral angle is 22.95 (11)° in 4'-cyanobiphenyl-4-yl-7-diethylamino-2-oxo-2H-chromene-3-carboxylate (II) (Sreenivasa et al., 2013), 62.97 (2)° in 4-(decyloxy)phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate (III) (Palakshamurthy, Sreenivasa et al., 2013), 21.00 (1)° in 4-(octyloxy)phenyl 2-oxo-2H-chromene-3-carboxylate (IV) (Palakshamurthy, Devarajegowda et al., 2013) and 54.46 (17)° in 4-[4-(heptyloxy)benzoyloxy] phenyl 2-oxo-7-trifluoromethyl-2H-chromene-3-carboxylate (V) (Devarajegowda, et al., 2013). Further, in (I), the torsions C9—C8—C10—O3, O3—C10—O4—C11 and C12—C11—O4—C10 have values 27.6 (4), 6.3 (3) and 124.6 (2)°, respectively.

Supramolecular features top

In the crystal structure, the molecules are connected along [001] via C12—H12···O3 interactions forming C(6) chains (Fig 2., Table 2). Further, neighbouring C(6) chains are interlocked via π···π interactions (Fig. 3), namely, Cg1··· Cg3ⁱ [3.7254 (15) Å, i: 1-x, 1/2+y, 1/2-z] and Cg2··· Cg3^i,ii [3.7303 (16) and 3.7716 (16) Å, ii: 1-x, 1/2+y, 1/2-z], where Cg1, Cg2 and Cg3 are the centroids of the C6/C7/C8/C9/O1/C1, C1–C6 and C11–C16 rings, respectively). Overall, a two-dimensional architecture is observed in the bc plane.

Synthesis and crystallization top

Coumarin 3-carboxylic acid (1.0 mmol), 4-bromophenol (1.0 mmol) and a catalytic amount of N,N-dimethylaminopyrimidine (DMAP) were dissolved in anhydrous CH₂Cl₂. To this solution, a solution of dicyclohexylcarbodimide (DCC) in dried CH₂Cl₂ was added and stirred. After 24 h of stirring, dicyclohexylurea was filtered off and the solution was concentrated. The solid residue obtained was purified by column chromatography on silica gel using CHCl₃ as the eluent. Single crystals suitable for X-ray studies were grown by slow evaporation technique at room temperature using ethanol as the solvent.

Refinement top

The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93Å, and with 1.2U_eq(C). Owing to poor agreement, several reflections, i.e. (0 2 5), (-1 0 2), (-2 0 8), (7 0 0) and (-7 2 5), were omitted from the final cycles of refinement.

Related literature top

For related structures, see: Sreenivasa et al. (2013); Palakshamurthy, Sreenivasa et al. (2013); Palakshamurthy, Devarajegowda et al. (2013); Devarajegowda et al. (2013). For the biological activity and other applications of 2-oxo-2H-chromene derivatives, see: Abdel-Aziz et al. (2013); Kostova (2006); Chandrasekharan & Kelly (2002).

Structure description top

For related structures, see: Sreenivasa et al. (2013); Palakshamurthy, Sreenivasa et al. (2013); Palakshamurthy, Devarajegowda et al. (2013); Devarajegowda et al. (2013). For the biological activity and other applications of 2-oxo-2H-chromene derivatives, see: Abdel-Aziz et al. (2013); Kostova (2006); Chandrasekharan & Kelly (2002).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound via C—H···O interactions along [001]. Hydrogen bonds are shown as dashed lines.
	Fig. 3. Various π–π interactions observed in the crystal packing

4-Bromophenyl-2-oxo-2H-chromene-3-carboxylate top

Crystal data top

C₁₆H₉BrO₄	Prism
M_r = 345.14	D_x = 1.678 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 523 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.0782 (10) Å	Cell parameters from 2395 reflections
b = 7.2618 (4) Å	θ = 2.8–25.0°
c = 12.7396 (8) Å	µ = 3.02 mm⁻¹
β = 113.311 (4)°	T = 296 K
V = 1366.01 (15) Å³	Prism, colourless
Z = 4	0.24 × 0.18 × 0.16 mm
F(000) = 688

Data collection top

Bruker APEXII CCD diffractometer	2395 independent reflections
Radiation source: fine-focus sealed tube	1831 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 2.01 pixels mm^-1	θ_max = 25.0°, θ_min = 2.8°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→8
T_min = 0.526, T_max = 0.617	l = −15→15
20483 measured reflections

Refinement top

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0319P)² + 0.8274P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2395 reflections	Δρ_max = 0.45 e Å⁻³
191 parameters	Δρ_min = −0.54 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.0062 (6)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₆H₉BrO₄	V = 1366.01 (15) Å³
M_r = 345.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.0782 (10) Å	µ = 3.02 mm⁻¹
b = 7.2618 (4) Å	T = 296 K
c = 12.7396 (8) Å	0.24 × 0.18 × 0.16 mm
β = 113.311 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2395 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	1831 reflections with I > 2σ(I)
T_min = 0.526, T_max = 0.617	R_int = 0.037
20483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.01	Δρ_max = 0.45 e Å⁻³
2395 reflections	Δρ_min = −0.54 e Å⁻³
191 parameters

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.

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

	x	y	z	U_iso*/U_eq
Br1	0.94359 (2)	0.14526 (6)	0.64830 (3)	0.0907 (2)
O1	0.31144 (12)	0.1686 (2)	−0.06316 (14)	0.0517 (5)
O2	0.44603 (13)	0.1964 (3)	−0.06745 (15)	0.0612 (5)
O3	0.58965 (12)	0.2657 (3)	0.15291 (14)	0.0556 (5)
O4	0.56890 (11)	0.0734 (2)	0.27929 (13)	0.0428 (4)
C1	0.25543 (17)	0.1424 (3)	−0.0061 (2)	0.0460 (6)
C2	0.1631 (2)	0.1504 (4)	−0.0694 (3)	0.0613 (8)
H2	0.1403	0.1720	−0.1477	0.074*
C3	0.1059 (2)	0.1257 (4)	−0.0142 (3)	0.0709 (9)
H3	0.0436	0.1322	−0.0558	0.085*
C4	0.1389 (2)	0.0915 (4)	0.1017 (3)	0.0673 (9)
H4	0.0990	0.0734	0.1372	0.081*
C5	0.23074 (18)	0.0840 (4)	0.1648 (3)	0.0547 (7)
H5	0.2530	0.0613	0.2429	0.066*
C6	0.29078 (17)	0.1108 (3)	0.1108 (2)	0.0413 (6)
C7	0.38706 (16)	0.1145 (3)	0.1709 (2)	0.0394 (6)
H7	0.4122	0.0939	0.2493	0.047*
C8	0.44200 (16)	0.1472 (3)	0.11609 (19)	0.0364 (6)
C9	0.40485 (18)	0.1736 (3)	−0.0079 (2)	0.0440 (6)
C10	0.54071 (17)	0.1702 (3)	0.18007 (19)	0.0385 (6)
C11	0.65769 (16)	0.0988 (3)	0.36007 (19)	0.0370 (5)
C12	0.66608 (17)	0.1487 (3)	0.4677 (2)	0.0433 (6)
H12	0.6149	0.1711	0.4827	0.052*
C13	0.75178 (19)	0.1654 (4)	0.5536 (2)	0.0517 (7)
H13	0.7590	0.2000	0.6270	0.062*
C14	0.82608 (18)	0.1301 (4)	0.5288 (2)	0.0499 (7)
C15	0.81735 (18)	0.0805 (4)	0.4214 (2)	0.0538 (7)
H15	0.8686	0.0581	0.4065	0.065*
C16	0.73210 (17)	0.0637 (4)	0.3352 (2)	0.0452 (6)
H16	0.7251	0.0293	0.2619	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0491 (2)	0.1081 (3)	0.0795 (3)	−0.01632 (19)	−0.01221 (17)	0.0173 (2)
O1	0.0460 (11)	0.0681 (12)	0.0343 (9)	0.0056 (9)	0.0087 (8)	−0.0015 (8)
O2	0.0622 (13)	0.0888 (15)	0.0368 (10)	0.0067 (11)	0.0240 (10)	0.0059 (10)
O3	0.0497 (11)	0.0724 (13)	0.0443 (10)	−0.0097 (10)	0.0181 (9)	0.0127 (9)
O4	0.0364 (9)	0.0547 (10)	0.0336 (9)	−0.0038 (8)	0.0100 (7)	0.0081 (8)
C1	0.0401 (15)	0.0421 (15)	0.0489 (15)	0.0008 (11)	0.0102 (13)	−0.0059 (12)
C2	0.0473 (18)	0.0615 (19)	0.0576 (18)	0.0004 (14)	0.0020 (15)	−0.0034 (14)
C3	0.0383 (17)	0.064 (2)	0.096 (3)	−0.0063 (14)	0.0115 (18)	−0.0058 (18)
C4	0.0465 (18)	0.064 (2)	0.094 (3)	−0.0078 (15)	0.0305 (18)	−0.0008 (18)
C5	0.0470 (17)	0.0564 (17)	0.0636 (17)	−0.0055 (14)	0.0250 (15)	0.0011 (14)
C6	0.0403 (14)	0.0363 (14)	0.0455 (14)	0.0000 (11)	0.0150 (12)	−0.0028 (11)
C7	0.0421 (14)	0.0375 (13)	0.0367 (13)	0.0018 (11)	0.0135 (11)	−0.0006 (10)
C8	0.0421 (14)	0.0352 (13)	0.0316 (12)	0.0027 (10)	0.0144 (11)	−0.0010 (10)
C9	0.0464 (15)	0.0485 (15)	0.0335 (13)	0.0059 (12)	0.0121 (12)	−0.0013 (11)
C10	0.0433 (14)	0.0409 (14)	0.0336 (13)	0.0007 (11)	0.0178 (11)	−0.0006 (10)
C11	0.0333 (13)	0.0405 (13)	0.0354 (12)	−0.0006 (11)	0.0117 (10)	0.0040 (10)
C12	0.0401 (15)	0.0506 (15)	0.0407 (14)	0.0037 (12)	0.0177 (12)	0.0031 (11)
C13	0.0576 (18)	0.0535 (16)	0.0374 (14)	−0.0025 (13)	0.0120 (13)	0.0006 (12)
C14	0.0381 (15)	0.0502 (16)	0.0487 (16)	−0.0054 (12)	0.0036 (12)	0.0084 (12)
C15	0.0375 (15)	0.0610 (17)	0.0630 (18)	0.0030 (13)	0.0200 (14)	0.0106 (14)
C16	0.0445 (15)	0.0535 (16)	0.0399 (13)	0.0011 (12)	0.0192 (12)	0.0023 (12)

Geometric parameters (Å, º) top

Br1—C14	1.903 (3)	C5—H5	0.9300
O1—C1	1.376 (3)	C6—C7	1.430 (3)
O1—C9	1.384 (3)	C7—C8	1.346 (3)
O2—C9	1.200 (3)	C7—H7	0.9300
O3—C10	1.198 (3)	C8—C9	1.463 (3)
O4—C10	1.358 (3)	C8—C10	1.479 (3)
O4—C11	1.403 (3)	C11—C12	1.372 (3)
C1—C2	1.382 (4)	C11—C16	1.377 (3)
C1—C6	1.387 (4)	C12—C13	1.385 (4)
C2—C3	1.373 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.375 (4)
C3—C4	1.380 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.368 (4)
C4—C5	1.374 (4)	C15—C16	1.381 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.402 (4)	C16—H16	0.9300

C1—O1—C9	122.67 (19)	C9—C8—C10	118.1 (2)
C10—O4—C11	118.88 (18)	O2—C9—O1	116.2 (2)
O1—C1—C2	117.5 (2)	O2—C9—C8	127.5 (2)
O1—C1—C6	121.0 (2)	O1—C9—C8	116.3 (2)
C2—C1—C6	121.5 (3)	O3—C10—O4	123.6 (2)
C3—C2—C1	118.6 (3)	O3—C10—C8	126.2 (2)
C3—C2—H2	120.7	O4—C10—C8	110.2 (2)
C1—C2—H2	120.7	C12—C11—C16	121.9 (2)
C2—C3—C4	121.3 (3)	C12—C11—O4	115.9 (2)
C2—C3—H3	119.4	C16—C11—O4	122.1 (2)
C4—C3—H3	119.4	C11—C12—C13	119.1 (2)
C5—C4—C3	120.2 (3)	C11—C12—H12	120.4
C5—C4—H4	119.9	C13—C12—H12	120.4
C3—C4—H4	119.9	C14—C13—C12	119.0 (2)
C4—C5—C6	119.8 (3)	C14—C13—H13	120.5
C4—C5—H5	120.1	C12—C13—H13	120.5
C6—C5—H5	120.1	C15—C14—C13	121.6 (2)
C1—C6—C5	118.7 (2)	C15—C14—Br1	119.5 (2)
C1—C6—C7	117.9 (2)	C13—C14—Br1	118.9 (2)
C5—C6—C7	123.3 (2)	C14—C15—C16	119.7 (2)
C8—C7—C6	121.3 (2)	C14—C15—H15	120.2
C8—C7—H7	119.4	C16—C15—H15	120.2
C6—C7—H7	119.4	C11—C16—C15	118.7 (2)
C7—C8—C9	120.8 (2)	C11—C16—H16	120.7
C7—C8—C10	121.0 (2)	C15—C16—H16	120.7

C9—O1—C1—C2	176.4 (2)	C7—C8—C9—O1	2.0 (3)
C9—O1—C1—C6	−3.1 (4)	C10—C8—C9—O1	−173.9 (2)
O1—C1—C2—C3	−179.7 (2)	C11—O4—C10—O3	6.3 (3)
C6—C1—C2—C3	−0.2 (4)	C11—O4—C10—C8	−170.71 (19)
C1—C2—C3—C4	−0.7 (4)	C7—C8—C10—O3	−148.3 (3)
C2—C3—C4—C5	0.9 (5)	C9—C8—C10—O3	27.6 (4)
C3—C4—C5—C6	−0.2 (4)	C7—C8—C10—O4	28.7 (3)
O1—C1—C6—C5	−179.7 (2)	C9—C8—C10—O4	−155.5 (2)
C2—C1—C6—C5	0.9 (4)	C10—O4—C11—C12	124.6 (2)
O1—C1—C6—C7	2.8 (3)	C10—O4—C11—C16	−59.7 (3)
C2—C1—C6—C7	−176.7 (2)	C16—C11—C12—C13	0.4 (4)
C4—C5—C6—C1	−0.7 (4)	O4—C11—C12—C13	176.2 (2)
C4—C5—C6—C7	176.7 (3)	C11—C12—C13—C14	−0.5 (4)
C1—C6—C7—C8	−0.1 (3)	C12—C13—C14—C15	0.5 (4)
C5—C6—C7—C8	−177.6 (2)	C12—C13—C14—Br1	−177.94 (19)
C6—C7—C8—C9	−2.2 (3)	C13—C14—C15—C16	−0.5 (4)
C6—C7—C8—C10	173.5 (2)	Br1—C14—C15—C16	178.0 (2)
C1—O1—C9—O2	179.7 (2)	C12—C11—C16—C15	−0.3 (4)
C1—O1—C9—C8	0.7 (3)	O4—C11—C16—C15	−175.9 (2)
C7—C8—C9—O2	−176.9 (3)	C14—C15—C16—C11	0.4 (4)
C10—C8—C9—O2	7.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3ⁱ	0.93	2.40	3.124 (3)	134

Symmetry code: (i) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3ⁱ	0.93	2.40	3.124 (3)	134

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

BSPM thanks the UGC–India for financial support under its Minor Research Project Scheme, and also acknowledges Mr Biraj, Tezpur University, Tezpur, for his help with the data collection.

References

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Volume 71| Part 5| May 2015| Pages o326-o327

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