catena-Poly[bis­(μ3-2-phenyl­acetato-κ3O,O′:O)bis­(μ2-2-phenyl­acetato-κ2O:O′)dicopper(II)(Cu—Cu)]

Benslimane, M.; Redjel, Y.K.; Merazig, H.; Daran, J.-C.

doi:10.1107/S160053681301581X

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page m397

https://doi.org/10.1107/S160053681301581X

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catena-Poly[bis(μ₃-2-phenylacetato-κ³O,O′:O)bis(μ₂-2-phenylacetato-κ²O:O′)dicopper(II)(Cu—Cu)]

Meriem Benslimane,^a ^* Yasmine Kheira Redjel,^a Hocine Merazig ^a and Jean-Claude Daran ^b

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, Faculté des Sciences Exactes, Département de Chimie, Université de Constantine 1, 25000 Constantine, Algeria, and ^bLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
^*Correspondence e-mail: b_meriem80@yahoo.fr

(Received 16 May 2013; accepted 6 June 2013; online 15 June 2013)

The title polymeric compound, [Cu₂(C₈H₇O₂)₄]_n, was synthesized by the reaction of copper acetate with aqueous phenylacetic acid. The unique Cu^II atom is coordinated by five O atoms from the carboxylate groups of phenylacetate ligands, and the strongly distorted octahedral coordination environment is completed by a Cu—Cu bond of 2.581 (2) Å, at whose mid-point is located an inversion centre. The crystal structure consists of infinite polymeric linear chains of Cu²⁺ ions, running along [100], linked by bridging phenylacetate groups.

Related literature

For the biological activity of divalent transition metals, see: Stem et al. (1990 ); Kimura (1994 ). For related compounds, see: Cui et al. (1999 ); Kong et al. (2005a ,b ).

Experimental

Crystal data

[Cu₂(C₈H₇O₂)₄]
M_r = 667.62
Monoclinic, P 2₁ /c
a = 5.1829 (6) Å
b = 26.328 (4) Å
c = 10.2279 (13) Å
β = 97.892 (7)°
V = 1382.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.59 mm⁻¹
T = 180 K
0.15 × 0.10 × 0.01 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.552, T_max = 0.745
4056 measured reflections
2382 independent reflections
1927 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.254
S = 1.20
2382 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 2.24 e Å⁻³
Δρ_min = −1.14 e Å⁻³

Data collection: APEX2 (Bruker, 2012 ); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681301581X/lr2106sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681301581X/lr2106Isup2.hkl

checkCIF report

Comment top

Carboxylate groups may interact as bridging ligands with divalent transition metals present in the biological environment, thereby altering the bioavailability of the drug. Moreover, it is well known that many complexes of divalent transition metals are capable of catalyzing the hydrolysis of RNA (Stem et al., 1990; Kimura, 1994). The coordination chemistry of polynuclear Cu²⁺ complexes bridged by phenylacetate has not been much reported. To date, we have found only two report of a dinuclear Co²⁺ complexes, namely tetrakis(phenylacetato)bis[(quinoline-N)-cobalt(II)] (Cui et al., 1999), µ-Aqua-κ²O:O-di-µ-phenylacetato-κ⁴O:O' -bis[(1,10-phenanthroline-κ²N,N')(phenylacetato- κO)cobalt(II)](Kong et al., 2005a) and dinuclear Cu²⁺ complex, namely tetrakis(phenylacetato)bis-[(N,N-dimethylformamide)copper(II)] (Kong et al., 2005b), in which all phenylacetate groups are in bidendate bridging modes. In this paper, we describe the crystal structure of new polymeric complex obtained by reaction of phenylacetic acid with copper(II) acetate.

The molecular geometry of the title compound is illustrated in Fig.1. Each Cu^II atom is six-coordinated by five O atoms from carboxylate groups of the phenylacetate and is completed by a Cu—Cu bond in a strongly distorted octahedral coordination, in which an inversion center is located at the mid-point of the Cu—Cu bond with a Cu···Cu distance is 2.581 (2) Å. The Cu—O bond length ranges from 1.944 (7) to 2.200 (6) Å. The two carboxylate groups [O3/C1/O1 and O2/C2/O4] are almost perpendicular to one another with a dihedral angle of 78.4 (16)°. The structure, consists of polymeric infinite linear chains running along [100](Fig.2). The chains are formed by Cu²⁺ ions linked with bridging phenylacetate groups.

Related literature top

For the biological activity of divalent transition metals, see: Stem et al. (1990; Kimura (1994). For related comopunds, see: Cui et al. (1999); Kong et al. (2005a,b).

Experimental top

To a solution of Cu(CH₃CO₂)₂.H₂O (0.049 g, 0.25 mmol) in methanol (10 cm³) at room temperature was added solid phenylacetic acid (0.068 g, 0.5 mmol) in small portions under constant stirring.The mixture was then filtered and the filtrate allowed to stand for 10 days, after which small blue block-like crystals of the title complex were obtained.

Structure description top

For the biological activity of divalent transition metals, see: Stem et al. (1990; Kimura (1994). For related comopunds, see: Cui et al. (1999); Kong et al. (2005a,b).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and 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 and H atoms are shown as small spheres of arbitrary radii.[Symmetry code: (i): 2 - x, -y, 1 - z].
	Fig. 2. A view of the crystal structure, showing chains along [100]. Hydrogen atoms have been omitted for clarity

catena-Poly[bis(µ₃-2-phenylacetato-κ³O,O':O)bis(µ₂-2-phenylacetato-κ²O:O')dicopper(II)(Cu—Cu)] top

Crystal data top

[Cu₂(C₈H₇O₂)₄]	F(000) = 684
M_r = 667.62	D_x = 1.604 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4583 reflections
a = 5.1829 (6) Å	θ = 3.1–26.3°
b = 26.328 (4) Å	µ = 1.59 mm⁻¹
c = 10.2279 (13) Å	T = 180 K
β = 97.892 (7)°	Box, blue
V = 1382.4 (3) Å³	0.15 × 0.1 × 0.01 mm
Z = 2

Data collection top

Bruker APEXII diffractometer	2382 independent reflections
Radiation source: fine-focus sealed tube	1927 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω and φ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
T_min = 0.552, T_max = 0.745	k = −22→31
4056 measured reflections	l = 0→12

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.082	w = 1/[σ²(F_o²) + (0.089P)² + 25.7899P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.254	(Δ/σ)_max = 0.003
S = 1.20	Δρ_max = 2.24 e Å⁻³
2382 reflections	Δρ_min = −1.14 e Å⁻³
190 parameters

Crystal data top

[Cu₂(C₈H₇O₂)₄]	V = 1382.4 (3) Å³
M_r = 667.62	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.1829 (6) Å	µ = 1.59 mm⁻¹
b = 26.328 (4) Å	T = 180 K
c = 10.2279 (13) Å	0.15 × 0.1 × 0.01 mm
β = 97.892 (7)°

Data collection top

Bruker APEXII diffractometer	2382 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1927 reflections with I > 2σ(I)
T_min = 0.552, T_max = 0.745	R_int = 0.036
4056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.254	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.089P)² + 25.7899P] where P = (F_o² + 2F_c²)/3
2382 reflections	Δρ_max = 2.24 e Å⁻³
190 parameters	Δρ_min = −1.14 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	0.9678 (18)	0.0897 (3)	0.4136 (9)	0.017 (2)
C2	0.8188 (19)	0.0341 (3)	0.7030 (10)	0.019 (2)
C11	0.948 (2)	0.1445 (4)	0.3711 (10)	0.024 (2)
H11A	0.8356	0.147	0.2874	0.028*
H11B	1.1195	0.1567	0.3582	0.028*
C12	0.840 (2)	0.1779 (4)	0.4725 (10)	0.023 (2)
C13	0.932 (2)	0.2267 (4)	0.4983 (12)	0.033 (3)
H13	1.0631	0.2391	0.4536	0.04*
C14	0.833 (3)	0.2573 (5)	0.5886 (14)	0.045 (3)
H14	0.8991	0.2898	0.6054	0.054*
C15	0.634 (3)	0.2395 (5)	0.6546 (12)	0.038 (3)
H15	0.5646	0.26	0.715	0.046*
C16	0.542 (2)	0.1914 (5)	0.6295 (12)	0.035 (3)
H16	0.4109	0.1791	0.6745	0.042*
C17	0.640 (2)	0.1606 (4)	0.5389 (12)	0.030 (2)
H17	0.5713	0.1282	0.5219	0.036*
C21	0.7117 (19)	0.0600 (4)	0.8179 (9)	0.021 (2)
H21A	0.585	0.0854	0.7834	0.025*
H21B	0.6227	0.0349	0.865	0.025*
C22	0.9225 (19)	0.0851 (4)	0.9136 (10)	0.020 (2)
C23	1.054 (2)	0.1279 (4)	0.8743 (10)	0.025 (2)
H23	0.9996	0.1426	0.7924	0.03*
C24	1.265 (2)	0.1486 (4)	0.9567 (11)	0.032 (3)
H24	1.3534	0.1765	0.9293	0.038*
C25	1.340 (2)	0.1274 (5)	1.0781 (11)	0.034 (3)
H25	1.4792	0.1414	1.1332	0.041*
C26	1.213 (2)	0.0860 (5)	1.1204 (11)	0.033 (3)
H26	1.2689	0.0717	1.2026	0.04*
C27	0.998 (2)	0.0652 (4)	1.0378 (10)	0.026 (2)
H27	0.9073	0.038	1.0672	0.031*
O1	1.1763 (13)	0.0758 (2)	0.4846 (7)	0.0213 (15)
O2	1.0628 (12)	0.0308 (3)	0.7092 (6)	0.0193 (15)
O3	1.2268 (13)	−0.0615 (3)	0.6233 (6)	0.0206 (15)
O4	1.3446 (11)	−0.0181 (2)	0.3911 (6)	0.0170 (14)
Cu1	1.2319 (2)	0.00810 (4)	0.56015 (11)	0.0143 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.016 (5)	0.023 (5)	0.014 (5)	−0.003 (4)	0.008 (4)	−0.001 (4)
C2	0.021 (5)	0.017 (5)	0.021 (5)	−0.003 (4)	0.008 (4)	−0.001 (4)
C11	0.023 (5)	0.028 (5)	0.020 (5)	0.001 (4)	0.002 (4)	0.003 (4)
C12	0.025 (6)	0.024 (5)	0.019 (5)	0.001 (4)	−0.002 (4)	0.002 (4)
C13	0.026 (6)	0.032 (6)	0.040 (7)	−0.003 (5)	−0.001 (5)	0.004 (5)
C14	0.049 (8)	0.027 (6)	0.059 (9)	−0.004 (6)	0.010 (7)	−0.013 (6)
C15	0.039 (7)	0.040 (7)	0.035 (7)	0.008 (5)	0.004 (6)	−0.011 (5)
C16	0.026 (6)	0.044 (7)	0.035 (7)	0.008 (5)	0.012 (5)	0.004 (5)
C17	0.027 (6)	0.022 (5)	0.041 (7)	−0.003 (4)	0.002 (5)	−0.003 (5)
C21	0.013 (5)	0.040 (6)	0.010 (5)	−0.001 (4)	0.003 (4)	−0.009 (4)
C22	0.011 (5)	0.034 (5)	0.016 (5)	0.002 (4)	0.000 (4)	−0.008 (4)
C23	0.023 (5)	0.040 (6)	0.013 (5)	0.000 (4)	0.001 (4)	−0.004 (4)
C24	0.026 (6)	0.037 (6)	0.032 (6)	−0.011 (5)	0.001 (5)	−0.012 (5)
C25	0.030 (6)	0.050 (7)	0.021 (6)	−0.002 (5)	−0.007 (5)	−0.016 (5)
C26	0.035 (7)	0.047 (7)	0.013 (5)	0.005 (5)	−0.007 (5)	−0.010 (5)
C27	0.028 (6)	0.036 (6)	0.015 (5)	−0.002 (5)	0.008 (5)	−0.004 (4)
O1	0.014 (3)	0.023 (3)	0.027 (4)	0.000 (3)	0.001 (3)	0.001 (3)
O2	0.006 (3)	0.035 (4)	0.017 (3)	0.002 (3)	0.001 (3)	−0.006 (3)
O3	0.023 (4)	0.025 (4)	0.014 (3)	0.000 (3)	0.002 (3)	0.002 (3)
O4	0.005 (3)	0.030 (4)	0.016 (3)	0.000 (3)	0.002 (3)	−0.005 (3)
Cu1	0.0114 (6)	0.0186 (6)	0.0134 (6)	−0.0004 (4)	0.0033 (4)	−0.0023 (5)

Geometric parameters (Å, º) top

C1—O3ⁱ	1.267 (11)	C21—H21B	0.97
C1—O1	1.270 (12)	C22—C27	1.380 (15)
C1—C11	1.507 (13)	C22—C23	1.402 (15)
C2—O2	1.261 (12)	C23—C24	1.397 (14)
C2—O4ⁱ	1.264 (12)	C23—H23	0.93
C2—C21	1.527 (13)	C24—C25	1.368 (16)
C11—C12	1.524 (14)	C24—H24	0.93
C11—H11A	0.97	C25—C26	1.371 (17)
C11—H11B	0.97	C25—H25	0.93
C12—C13	1.381 (15)	C26—C27	1.414 (15)
C12—C17	1.395 (15)	C26—H26	0.93
C13—C14	1.377 (17)	C27—H27	0.93
C13—H13	0.93	O1—Cu1	1.948 (7)
C14—C15	1.388 (19)	O2—Cu1	1.954 (6)
C14—H14	0.93	O3—C1ⁱ	1.267 (11)
C15—C16	1.365 (17)	O3—Cu1	1.944 (7)
C15—H15	0.93	O4—C2ⁱ	1.264 (12)
C16—C17	1.379 (16)	O4—Cu1	2.021 (6)
C16—H16	0.93	O4—Cu1ⁱⁱ	2.199 (6)
C17—H17	0.93	Cu1—O4ⁱⁱ	2.199 (6)
C21—C22	1.515 (13)	Cu1—Cu1ⁱ	2.581 (2)
C21—H21A	0.97

O3ⁱ—C1—O1	125.6 (9)	C23—C22—C21	120.0 (9)
O3ⁱ—C1—C11	117.1 (9)	C24—C23—C22	120.7 (10)
O1—C1—C11	117.3 (8)	C24—C23—H23	119.6
O2—C2—O4ⁱ	125.3 (9)	C22—C23—H23	119.6
O2—C2—C21	117.4 (9)	C25—C24—C23	119.3 (11)
O4ⁱ—C2—C21	117.3 (8)	C25—C24—H24	120.4
C1—C11—C12	111.9 (8)	C23—C24—H24	120.4
C1—C11—H11A	109.2	C24—C25—C26	121.5 (10)
C12—C11—H11A	109.2	C24—C25—H25	119.3
C1—C11—H11B	109.2	C26—C25—H25	119.3
C12—C11—H11B	109.2	C25—C26—C27	119.4 (10)
H11A—C11—H11B	107.9	C25—C26—H26	120.3
C13—C12—C17	118.0 (10)	C27—C26—H26	120.3
C13—C12—C11	121.2 (10)	C22—C27—C26	120.3 (10)
C17—C12—C11	120.7 (9)	C22—C27—H27	119.9
C14—C13—C12	121.5 (11)	C26—C27—H27	119.9
C14—C13—H13	119.3	C1—O1—Cu1	123.9 (6)
C12—C13—H13	119.3	C2—O2—Cu1	122.4 (6)
C13—C14—C15	119.9 (11)	C1ⁱ—O3—Cu1	119.9 (6)
C13—C14—H14	120	C2ⁱ—O4—Cu1	121.6 (6)
C15—C14—H14	120	C2ⁱ—O4—Cu1ⁱⁱ	139.1 (6)
C16—C15—C14	119.0 (11)	Cu1—O4—Cu1ⁱⁱ	99.3 (3)
C16—C15—H15	120.5	O3—Cu1—O1	170.4 (3)
C14—C15—H15	120.5	O3—Cu1—O2	90.1 (3)
C15—C16—C17	121.4 (11)	O1—Cu1—O2	88.4 (3)
C15—C16—H16	119.3	O3—Cu1—O4	88.9 (3)
C17—C16—H16	119.3	O1—Cu1—O4	91.0 (3)
C16—C17—C12	120.1 (10)	O2—Cu1—O4	170.2 (3)
C16—C17—H17	119.9	O3—Cu1—O4ⁱⁱ	95.5 (3)
C12—C17—H17	119.9	O1—Cu1—O4ⁱⁱ	93.9 (3)
C22—C21—C2	112.7 (8)	O2—Cu1—O4ⁱⁱ	109.1 (3)
C22—C21—H21A	109.1	O4—Cu1—O4ⁱⁱ	80.7 (3)
C2—C21—H21A	109.1	O3—Cu1—Cu1ⁱ	87.0 (2)
C22—C21—H21B	109.1	O1—Cu1—Cu1ⁱ	83.4 (2)
C2—C21—H21B	109.1	O2—Cu1—Cu1ⁱ	86.24 (19)
H21A—C21—H21B	107.8	O4—Cu1—Cu1ⁱ	83.99 (18)
C27—C22—C23	118.8 (9)	O4ⁱⁱ—Cu1—Cu1ⁱ	164.41 (18)
C27—C22—C21	121.1 (9)

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

Experimental details

Crystal data
Chemical formula	[Cu₂(C₈H₇O₂)₄]
M_r	667.62
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	180
a, b, c (Å)	5.1829 (6), 26.328 (4), 10.2279 (13)
β (°)	97.892 (7)
V (Å³)	1382.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.59
Crystal size (mm)	0.15 × 0.1 × 0.01

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.552, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	4056, 2382, 1927
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.254, 1.20
No. of reflections	2382
No. of parameters	190
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.089P)² + 25.7899P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.24, −1.14

Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012).

Acknowledgements

This work was supported by the University of Constantine 1.

References

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