{4-Dimethyl­amino-N′-[1-(2-oxidophen­yl)ethyl­idene]benzohydrazidato}(methano­lato)oxidovanadium(V)

Wang, C.-Y.; Hu, J.-J.; Tu, H.-Y.; Zhu, P.-F.; Sheng, S.-J.

doi:10.1107/S1600536811050173

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1836

https://doi.org/10.1107/S1600536811050173

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{4-Dimethylamino-N′-[1-(2-oxidophenyl)ethylidene]benzohydrazidato}(methanolato)oxidovanadium(V)

Chen-Yi Wang,^a ^* Juan-Juan Hu,^b Hai-Yu Tu,^a Pei-Fei Zhu ^a and Su-Jun Sheng ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China, and ^bHuzhou No. 11 Middle School, Huzhou 313000, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 2 October 2011; accepted 22 November 2011; online 25 November 2011)

The title oxidovanadium(V) complex, [V(C₁₇H₁₇N₃O₂)(CH₃O)O], was obtained by the reaction of 2-acetylphenol, 4-dimethylaminobenzohydrazide and vanadyl sulfate in methanol. The V^V atom is five-coordinated by N,O,O′-donor atoms of the Schiff base ligand, one methoxy O atom and one oxide O atom, forming a square-pyramidal geometry.

Related literature

For Schiff base complexes, see: Wang (2009 ); Wang & Ye (2011 ). For similar oxidovanadium complexes, see: Deng et al. (2005 ); Gao et al. (2005 ); Huo et al. (2004 ).

Experimental

Crystal data

[V(C₁₇H₁₇N₃O₂)(CH₃O)O]
M_r = 393.31
Monoclinic, P 2₁ /n
a = 7.4670 (15) Å
b = 16.769 (3) Å
c = 14.301 (3) Å
β = 97.317 (3)°
V = 1776.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.59 mm⁻¹
T = 298 K
0.37 × 0.35 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.812, T_max = 0.834
14014 measured reflections
3784 independent reflections
2320 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.083
wR(F²) = 0.185
S = 1.04
3784 reflections
239 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Selected bond lengths (Å)

V1—O2	1.584 (4)
V1—O3	1.781 (3)
V1—O1	1.830 (3)
V1—O4	1.891 (3)
V1—N1	2.087 (4)

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811050173/qm2035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050173/qm2035Isup2.hkl

checkCIF report

Comment top

As part of our investigations into new Schiff base complexes (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear oxovanadium(V) complex, Fig. 1. The V atom in the complex is five-coordinated by the NOO donor atoms of the Schiff base ligand, one methoxy O atom, and one oxo O atom, forming a square pyramidal geometry. The V–O and V–N bond lengths (Table 1) are typical and are comparable with those observed in other similar vanadium complexes (Deng et al., 2005; Gao et al., 2005; Huo et al., 2004). The dihedral angle between the two benzene rings is 9.6 (3)°.

Related literature top

For Schiff base complexes, see: Wang (2009); Wang & Ye (2011). For similar oxidovanadium complexes, see: Deng et al. (2005); Gao et al. (2005); Huo et al. (2004).

Experimental top

2-Acetylphenol (1.0 mmol, 0.14 g), 4-dimethylaminobenzohydrazide (1.0 mmol, 0.18 g), and vanadyl sulfate (1.0 mmol, 0.16 g) were dissolved in methanol (30 ml). The mixture was stirred at room temperature for 10 min to give a clear brown solution. After keeping the solution in air for a week, brown block-shaped crystals were formed at the bottom of the vessel.

Structure description top

For Schiff base complexes, see: Wang (2009); Wang & Ye (2011). For similar oxidovanadium complexes, see: Deng et al. (2005); Gao et al. (2005); Huo et al. (2004).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

{4-Dimethylamino-N'-[1-(2- oxidophenyl)ethylidene]benzohydrazidato}(methanolato)oxidovanadium(V) top

Crystal data top

[V(C₁₇H₁₇N₃O₂)(CH₃O)O]	F(000) = 816
M_r = 393.31	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4670 (15) Å	Cell parameters from 1094 reflections
b = 16.769 (3) Å	θ = 2.5–24.5°
c = 14.301 (3) Å	µ = 0.59 mm⁻¹
β = 97.317 (3)°	T = 298 K
V = 1776.1 (6) Å³	Block, brown
Z = 4	0.37 × 0.35 × 0.32 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3784 independent reflections
Radiation source: fine-focus sealed tube	2320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ω scan	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.812, T_max = 0.834	k = −21→21
14014 measured reflections	l = −17→17

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.185	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0631P)² + 2.2577P] where P = (F_o² + 2F_c²)/3
3784 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[V(C₁₇H₁₇N₃O₂)(CH₃O)O]	V = 1776.1 (6) Å³
M_r = 393.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4670 (15) Å	µ = 0.59 mm⁻¹
b = 16.769 (3) Å	T = 298 K
c = 14.301 (3) Å	0.37 × 0.35 × 0.32 mm
β = 97.317 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3784 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2320 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.834	R_int = 0.086
14014 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.083	0 restraints
wR(F²) = 0.185	H-atom parameters constrained
S = 1.04	Δρ_max = 0.41 e Å⁻³
3784 reflections	Δρ_min = −0.35 e Å⁻³
239 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.

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
V1	0.10795 (12)	0.13127 (5)	0.77749 (6)	0.0388 (3)
N1	0.1980 (5)	0.1517 (2)	0.9197 (3)	0.0358 (9)
N2	0.2327 (6)	0.0829 (2)	0.9744 (3)	0.0408 (10)
N3	0.3041 (7)	−0.2889 (3)	1.0718 (3)	0.0524 (12)
O1	0.0163 (5)	0.23203 (18)	0.7837 (2)	0.0412 (9)
O2	0.2945 (5)	0.1411 (2)	0.7370 (2)	0.0504 (9)
O3	−0.0496 (5)	0.0947 (2)	0.6833 (2)	0.0492 (10)
O4	0.1059 (5)	0.02996 (19)	0.8355 (2)	0.0461 (9)
C1	0.1993 (7)	0.2944 (3)	0.9142 (3)	0.0384 (12)
C2	0.0922 (7)	0.2980 (3)	0.8249 (4)	0.0403 (12)
C3	0.0610 (7)	0.3703 (3)	0.7791 (4)	0.0492 (13)
H3	−0.0122	0.3726	0.7215	0.059*
C4	0.1378 (8)	0.4385 (3)	0.8187 (5)	0.0592 (16)
H4	0.1179	0.4868	0.7871	0.071*
C5	0.2445 (9)	0.4365 (4)	0.9049 (5)	0.0658 (18)
H5	0.2977	0.4830	0.9309	0.079*
C6	0.2712 (8)	0.3661 (3)	0.9516 (4)	0.0555 (15)
H6	0.3400	0.3657	1.0106	0.067*
C7	0.2311 (7)	0.2191 (3)	0.9642 (3)	0.0402 (12)
C8	0.3029 (8)	0.2198 (3)	1.0662 (4)	0.0557 (15)
H8A	0.2411	0.1803	1.0987	0.084*
H8B	0.2842	0.2715	1.0921	0.084*
H8C	0.4297	0.2080	1.0736	0.084*
C9	0.1847 (7)	0.0219 (3)	0.9224 (3)	0.0397 (12)
C10	0.2147 (7)	−0.0592 (3)	0.9614 (3)	0.0393 (12)
C11	0.1577 (7)	−0.1257 (3)	0.9080 (3)	0.0446 (13)
H11	0.0989	−0.1189	0.8472	0.053*
C12	0.1870 (7)	−0.2012 (3)	0.9435 (4)	0.0444 (13)
H12	0.1489	−0.2448	0.9059	0.053*
C13	0.2734 (7)	−0.2142 (3)	1.0356 (3)	0.0396 (12)
C14	0.3301 (7)	−0.1464 (3)	1.0886 (3)	0.0434 (13)
H14	0.3884	−0.1525	1.1496	0.052*
C15	0.3009 (7)	−0.0714 (3)	1.0520 (3)	0.0443 (13)
H15	0.3400	−0.0275	1.0888	0.053*
C16	0.3821 (8)	−0.3013 (3)	1.1697 (4)	0.0532 (15)
H16A	0.4991	−0.2768	1.1802	0.080*
H16B	0.3934	−0.3574	1.1822	0.080*
H16C	0.3050	−0.2778	1.2109	0.080*
C17	0.2427 (9)	−0.3588 (3)	1.0172 (4)	0.0625 (17)
H17A	0.1134	−0.3619	1.0116	0.094*
H17B	0.2941	−0.4058	1.0483	0.094*
H17C	0.2800	−0.3551	0.9555	0.094*
C18	−0.2125 (9)	0.0551 (4)	0.6885 (4)	0.0698 (19)
H18A	−0.1942	0.0135	0.7349	0.105*
H18B	−0.2551	0.0322	0.6282	0.105*
H18C	−0.3003	0.0922	0.7059	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
V1	0.0510 (6)	0.0343 (5)	0.0295 (4)	0.0004 (4)	−0.0007 (4)	−0.0003 (4)
N1	0.037 (2)	0.033 (2)	0.036 (2)	0.0009 (18)	0.0023 (18)	−0.0049 (17)
N2	0.050 (3)	0.038 (2)	0.034 (2)	0.002 (2)	0.0012 (19)	0.0052 (19)
N3	0.076 (3)	0.044 (3)	0.037 (2)	0.006 (2)	0.007 (2)	0.000 (2)
O1	0.047 (2)	0.0345 (19)	0.0398 (19)	0.0037 (16)	−0.0043 (16)	−0.0023 (15)
O2	0.056 (2)	0.051 (2)	0.045 (2)	0.0061 (18)	0.0107 (18)	−0.0004 (17)
O3	0.067 (3)	0.040 (2)	0.037 (2)	−0.0089 (19)	−0.0069 (18)	0.0006 (16)
O4	0.063 (2)	0.039 (2)	0.0331 (19)	0.0004 (18)	−0.0069 (17)	0.0053 (15)
C1	0.039 (3)	0.039 (3)	0.040 (3)	−0.003 (2)	0.014 (2)	−0.015 (2)
C2	0.039 (3)	0.035 (3)	0.049 (3)	0.002 (2)	0.010 (2)	−0.009 (2)
C3	0.057 (4)	0.042 (3)	0.050 (3)	−0.001 (3)	0.009 (3)	−0.003 (3)
C4	0.068 (4)	0.043 (3)	0.070 (4)	0.002 (3)	0.021 (3)	0.000 (3)
C5	0.069 (4)	0.047 (4)	0.084 (5)	−0.020 (3)	0.018 (4)	−0.023 (3)
C6	0.056 (4)	0.053 (4)	0.059 (4)	−0.007 (3)	0.011 (3)	−0.017 (3)
C7	0.042 (3)	0.044 (3)	0.036 (3)	0.000 (2)	0.008 (2)	−0.003 (2)
C8	0.062 (4)	0.062 (4)	0.040 (3)	−0.002 (3)	−0.005 (3)	−0.012 (3)
C9	0.034 (3)	0.047 (3)	0.040 (3)	0.000 (2)	0.012 (2)	−0.004 (2)
C10	0.041 (3)	0.042 (3)	0.035 (3)	0.002 (2)	0.007 (2)	0.009 (2)
C11	0.046 (3)	0.052 (3)	0.034 (3)	−0.003 (3)	0.001 (2)	0.000 (3)
C12	0.051 (3)	0.041 (3)	0.041 (3)	−0.007 (3)	0.004 (3)	−0.005 (2)
C13	0.043 (3)	0.038 (3)	0.039 (3)	0.002 (2)	0.011 (2)	0.007 (2)
C14	0.048 (3)	0.047 (3)	0.032 (3)	0.006 (2)	−0.006 (2)	0.002 (2)
C15	0.053 (3)	0.041 (3)	0.038 (3)	−0.004 (3)	0.001 (2)	0.000 (2)
C16	0.064 (4)	0.052 (3)	0.044 (3)	0.013 (3)	0.008 (3)	0.013 (3)
C17	0.083 (5)	0.050 (4)	0.056 (4)	0.006 (3)	0.010 (3)	0.002 (3)
C18	0.082 (5)	0.075 (4)	0.050 (4)	−0.021 (4)	−0.005 (3)	−0.009 (3)

Geometric parameters (Å, º) top

V1—O2	1.584 (4)	C7—C8	1.489 (7)
V1—O3	1.781 (3)	C8—H8A	0.9600
V1—O1	1.830 (3)	C8—H8B	0.9600
V1—O4	1.891 (3)	C8—H8C	0.9600
V1—N1	2.087 (4)	C9—C10	1.477 (7)
N1—C7	1.305 (6)	C10—C15	1.386 (7)
N1—N2	1.399 (5)	C10—C11	1.387 (7)
N2—C9	1.289 (6)	C11—C12	1.372 (7)
N3—C13	1.363 (6)	C11—H11	0.9300
N3—C17	1.451 (7)	C12—C13	1.408 (7)
N3—C16	1.461 (6)	C12—H12	0.9300
O1—C2	1.343 (5)	C13—C14	1.401 (7)
O3—C18	1.396 (7)	C14—C15	1.369 (7)
O4—C9	1.312 (6)	C14—H14	0.9300
C1—C6	1.395 (7)	C15—H15	0.9300
C1—C2	1.420 (7)	C16—H16A	0.9600
C1—C7	1.456 (7)	C16—H16B	0.9600
C2—C3	1.384 (7)	C16—H16C	0.9600
C3—C4	1.369 (7)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—C5	1.381 (8)	C17—H17C	0.9600
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.358 (8)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—H6	0.9300

O2—V1—O3	106.64 (18)	H8A—C8—H8B	109.5
O2—V1—O1	105.91 (17)	C7—C8—H8C	109.5
O3—V1—O1	98.04 (16)	H8A—C8—H8C	109.5
O2—V1—O4	108.07 (17)	H8B—C8—H8C	109.5
O3—V1—O4	88.89 (15)	N2—C9—O4	121.5 (5)
O1—V1—O4	141.65 (16)	N2—C9—C10	119.7 (5)
O2—V1—N1	98.64 (17)	O4—C9—C10	118.8 (4)
O3—V1—N1	153.28 (17)	C15—C10—C11	118.0 (5)
O1—V1—N1	82.92 (15)	C15—C10—C9	121.3 (5)
O4—V1—N1	74.93 (14)	C11—C10—C9	120.7 (5)
C7—N1—N2	115.5 (4)	C12—C11—C10	121.0 (5)
C7—N1—V1	129.4 (3)	C12—C11—H11	119.5
N2—N1—V1	115.0 (3)	C10—C11—H11	119.5
C9—N2—N1	108.3 (4)	C11—C12—C13	121.4 (5)
C13—N3—C17	120.8 (4)	C11—C12—H12	119.3
C13—N3—C16	121.5 (4)	C13—C12—H12	119.3
C17—N3—C16	117.4 (4)	N3—C13—C14	121.0 (5)
C2—O1—V1	129.9 (3)	N3—C13—C12	122.1 (5)
C18—O3—V1	128.3 (3)	C14—C13—C12	116.9 (4)
C9—O4—V1	118.7 (3)	C15—C14—C13	121.1 (5)
C6—C1—C2	117.0 (5)	C15—C14—H14	119.5
C6—C1—C7	121.9 (5)	C13—C14—H14	119.5
C2—C1—C7	121.1 (4)	C14—C15—C10	121.6 (5)
O1—C2—C3	118.6 (5)	C14—C15—H15	119.2
O1—C2—C1	121.2 (4)	C10—C15—H15	119.2
C3—C2—C1	120.2 (5)	N3—C16—H16A	109.5
C4—C3—C2	120.0 (5)	N3—C16—H16B	109.5
C4—C3—H3	120.0	H16A—C16—H16B	109.5
C2—C3—H3	120.0	N3—C16—H16C	109.5
C3—C4—C5	120.9 (6)	H16A—C16—H16C	109.5
C3—C4—H4	119.6	H16B—C16—H16C	109.5
C5—C4—H4	119.6	N3—C17—H17A	109.5
C6—C5—C4	119.5 (5)	N3—C17—H17B	109.5
C6—C5—H5	120.3	H17A—C17—H17B	109.5
C4—C5—H5	120.3	N3—C17—H17C	109.5
C5—C6—C1	122.3 (6)	H17A—C17—H17C	109.5
C5—C6—H6	118.8	H17B—C17—H17C	109.5
C1—C6—H6	118.8	O3—C18—H18A	109.5
N1—C7—C1	120.2 (4)	O3—C18—H18B	109.5
N1—C7—C8	120.5 (5)	H18A—C18—H18B	109.5
C1—C7—C8	119.3 (5)	O3—C18—H18C	109.5
C7—C8—H8A	109.5	H18A—C18—H18C	109.5
C7—C8—H8B	109.5	H18B—C18—H18C	109.5

Experimental details

Crystal data
Chemical formula	[V(C₁₇H₁₇N₃O₂)(CH₃O)O]
M_r	393.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.4670 (15), 16.769 (3), 14.301 (3)
β (°)	97.317 (3)
V (Å³)	1776.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.37 × 0.35 × 0.32

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.812, 0.834
No. of measured, independent and observed [I > 2σ(I)] reflections	14014, 3784, 2320
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.083, 0.185, 1.04
No. of reflections	3784
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.35

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

V1—O2	1.584 (4)	V1—O4	1.891 (3)
V1—O3	1.781 (3)	V1—N1	2.087 (4)
V1—O1	1.830 (3)

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Applied Research Project on Nonprofit Technology of Zhejiang Province (No. 2010 C32060), the Zhejiang Provincial Natural Science Foundation of China (No. Y407318), and the Technological Innovation Project (Sinfonietta Talent Plan) of College Students in Zhejiang Province (Nos. 2010R42525 and 2011R425027).

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