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1.  Redetermination of {5-[(7-chloro­quinolinium-4-yl)amino]-2-hy­droxy­benz­yl}diethyl­ammonium dichloride dihydrate 
The structure of the title compound (common name: amodiaquinium dichloride dihydrate), C20H24ClN3O2 +·2Cl−·2H2O, was previously determined from powder diffraction data [Llinàs et al. (2006 ▶). Acta Cryst. E62, o4196-o4199]. It has now been refined from diffractometer data to a significantly higher precision. The dihedral angle between the quinoline and benzene rings is 54.57 (6)°. The central amino N atom inter­acts more strongly with the quinoline ring than with the benzene ring, as indicated by the shorter C—N bond length [1.341 (2) Å compared to 1.431 (2) Å]. In the crystal, mol­ecules are packed into a three-dimensional network/supra­molecular structure through hydrogen bonds between the amodiaquinium cations, chloride anions and water mol­ecules.
PMCID: PMC3007921  PMID: 21588696
2.  Redetermination of 4-(dimethyl­amino)­pyridinium tribromide 
In the title salt, C7H11N2 +·Br3 −, the essentially planar cation (r.m.s. deviation = 0.006 Å) forms an N—H⋯Br hydrogen bond to one of the Br atoms of the almost linear anion [Br—Br—Br = 179.31 (2)°]. The crystal studied was found to be a racemic twin. The whole-mol­ecule disorder of the cation and anion about a twofold rotation axis described earlier [Ng (2009). Acta Cryst. E65, o1276] is an artifact of halving one of the axes of the ortho­rhom­bic unit cell.
PMCID: PMC3008028  PMID: 21588594
3.  Hexa­kis­(thio­urea-κS)nickel(II) nitrate: a redetermination 
A preliminary X-ray study of the title mol­ecular salt, [Ni(CH4N2S)6](NO3)2, has been reported twice previously, by Maďar [Acta Cryst. (1961), 14, 894] and Rodriguez, Cubero, Vega, Morente & Vazquez [Acta Cryst. (1961), 14, 1101], using film methods. We confirm the previous studies, but to modern standards of precision and with all H atoms located. The central Ni atom (site symmetry ) of the dication is octa­hedrally coordinated by six S-bound thio­urea mol­ecules. The crystal structure is stabilized by intra- and inter­molecular N—H⋯S and N—H⋯O hydrogen bonds.
PMCID: PMC3007420  PMID: 21588080
4.  Redetermination of 2,6-dimethoxy­benzoic acid 
The crystal structure of the title compound, C9H10O4, was first reported by Swaminathan, Vimala & Lotter [Acta Cryst. (1976), B32, 1897–1900]. It has been re-examined, improving the precision of the derived geometric parameters. The asymmetric unit comprises a non-planar independent mol­ecule, as the meth­oxy substituents force the carb­oxy group to be twisted away from the plane of the aromatic ring by 56.12 (9)°. Due to the anti­planar conformation adopted by the OH group, the mol­ecular components do not form the conventional dimeric units, but are associated in the crystal in chains stabilized by linear O—H⋯O hydrogen bonds, involving the OH groups and the carbonyl O atoms, which form C(3) motifs.
PMCID: PMC2968263  PMID: 21581932
5.  Redetermination of (E)-3-(anthracen-9-yl)-1-(2-hy­droxy­phen­yl)prop-2-en-1-one1  
The redetermined structure of title chalcone derivative, C23H16O2, corrects errors in the title, scheme and synthesis in the previous report of the same structure [Jasinski et al. (2011 ▶). Acta Cryst. E67, o795]. There are two independent mol­ecules in the asymmetric unit with slight differences in bond lengths and angles. The dihedral angle between the benzene ring and the anthracene ring system is 73.30 (4)° in one mol­ecule and 73.18 (4)° in the other. Both mol­ecules feature an intra­molecular O—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol­ecules are arranged into sheets lying parallel to the ac plane and further stacked along the b axis by π–π inter­actions with centroid–centroid distances in the range 3.6421 (6)–3.7607 (6) Å. The crystal structure is further stabilized by C—H⋯π inter­actions. There are also C⋯O [3.2159 (15) Å] short contacts.
PMCID: PMC3201364  PMID: 22065671
6.  Crystal structure of di­chlorido­(2,2′:6′,2′′-terpyridine-κ3 N,N′,N′′)zinc: a redeter­min­ation 
The crystal structure of the title compound, [ZnCl2(C15H11N3)], was redetermined based on modern CCD data. In comparison with the previous determination from photographic film data [Corbridge & Cox (1956 ▶). J. Chem. Soc. 159, 594–603; Einstein & Penfold (1966 ▶). Acta Cryst. 20, 924–926], all non-H atoms were refined with anisotropic displacement parameters, leading to a much higher precision in terms of bond lengths and angles [e.g. Zn—Cl = 2.2684 (8) and 2.2883 (11) compared to 2.25 (1) and 2.27 (1) Å]. In the title mol­ecule, the ZnII atom is five-coordinated in a distorted square-pyramidal mode by two Cl atoms and by the three N atoms from the 2,2′:6′,2′′-terpyridine ligand. The latter is not planar and shows dihedral angles between the least-squares planes of the central pyridine ring and the terminal rings of 3.18 (8) and 6.36 (9)°. The mol­ecules in the crystal structure pack with π–π inter­actions [centroid–centroid distance = 3.655 (2) Å] between pyridine rings of neighbouring terpyridine moieties. These, together with inter­molecular C—H⋯Cl inter­actions, stablize the three-dimensional structure.
PMCID: PMC4257341  PMID: 25484786
crystal structure; redetermination; 2,2′:6′,2′′-terpyridine; zinc complex; π–π inter­actions
7.  Piperazine-1,4-diium (R)-2-[4-(1-car­boxy­l­atometh­oxy)phen­oxy]propano­ate 
In the anion of the title mol­ecular salt, C4H12N2 2+·C11H10O6 2−, the two acetate groups form torsion angles of 74.1 (1) and 7.1 (1)° with the central benzene ring, and the cation exhibits a chair conformation. In the crystal, N—H⋯O hydrogen bonds link the components into a two-dimensional supra­molecular network lying parallel to the ab plane. A number of C—H⋯O inter­actions consolidate the packing.
PMCID: PMC3393966  PMID: 22798831
8.  1-[Bis(4-fluoro­phen­yl)meth­yl]-4-[(2Z)-3-phenyl­prop-2-en-1-yl]piperazine-1,4-diium dichloride hemihydrate 
The asymmetric unit of the title monohydrated salt, 2C26H28F2N2 2+·4Cl−.H2O, consists of a 1-[bis­(4-fluoro­phen­yl)meth­yl]-4-[(2Z)-3-phenyl­prop-2-en-1-yl]piperazine-1,4-diium cation with a diprotonated piperizine ring in close proximity to two chloride anions and a single water mol­ecule that lies on a twofold rotation axis. In the cation, the piperazine ring adopts a slightly distorted chair conformation. The dihedral angles between the phenyl ring and the 4-fluoro­phenyl rings are 89.3 (9) and 35.0 (5)°. The two fluoro­phenyl rings are inclined at 65.0 (5)° to one another. In the crystal, N—H⋯Cl hydrogen bonds and weak C—H⋯Cl inter­molecular inter­actions link the mol­ecules into chains along [010]. In addition, weak C—H⋯O inter­actions between the piperizine and prop-2-en-1-yl groups with the water mol­ecule, along with weak C—H⋯Cl inter­actions between the prop-2en-1-yl and methyl groups with the chloride ions, weak C—H⋯F inter­actions between the two fluoro­phenyl groups and weak O—H⋯Cl inter­actions between the water mol­ecule and chloride ions form a three-dimensional supra­molecular network.
PMCID: PMC4051083  PMID: 24940270
9.  Piperazine-1,4-diium bis­(2,4,5-tricarb­oxy­benzoate) dihydrate 
In the title hydrated salt, C4H12N2 2+·2C10H5O8 −·2H2O, the piperazinediium cation, lying about an inversion center, adopts a chair conformation. The benzene ring of the anion makes dihedral angles of 25.17 (8)° with the carboxyl­ate group and angles of 8.50 (7), 20.07 (7) and 80.86 (8)° with the three carb­oxy­lic acid groups. In the crystal, the cations, anions and water mol­ecules are connected by O—H⋯O and N—H⋯O hydrogen bonds into double layers parallel to (110).
PMCID: PMC3629622  PMID: 23634109
10.  Redetermination of loperamide monohydrate 
The structure of the title compound {systematic name: 4-[4-(4-chloro­phen­yl)-4-hy­droxy­piperidin-1-yl]-N,N-dimethyl-2,2-di­phenyl­butanamide monohydrate}, C29H33ClN2O2·H2O, has been redetermined at 170 (2) K. The redetermination is of significantly higher precision than the previous structure determination at room temperature and includes the H-atom coordinates that were not included in the previous report [Germain et al. (1977 ▶). Acta Cryst. B33, 942–944]. It consists of a piperidin-1-yl ring in a distorted chair conformation, with the N,N-dimethyl-α,α-diphenyl­butyramide and the 4-chloro­phenyl and hy­droxy groups bonded in para positions and an external water mol­ecule within the asymmetric unit. The dihedral angles between the mean plane of the piperidine ring and the 4-chloro­phenyl and two benzene rings are 83.4 (5), 76.4 (2) and 85.9 (2)°, respectively. The two benzene rings are inclined to one another by 50.8 (6)°. In the crystal, mol­ecules are linked by O—H⋯O and O—H⋯N hydrogen bonds and weak C—H⋯O intermolecular interactions, forming an infinite two-dimensional network along [110].
PMCID: PMC3275278  PMID: 22347134
11.  Redetermined structure of diphenyl­phospho­nimidotriphenyl­phospho­rane: location of the hydrogen atoms and analysis of the inter­molecular inter­actions 
The title compound, C30H25NOP2, is a bulky phosphazene derivative. Its previous crystal structure [Cameron et al. (1979 ▶). Acta Cryst. B35, 1373–1377] is confirmed and its H atoms have been located in the present study. The formal P=N double bond is about 0.05 Å shorter than the P—N single bond and the large P=N—P bond angle reflects the steric strain in the mol­ecule. An intra­molecular C—H⋯O inter­action occurs. In the crystal, short C—H⋯O contacts connect the mol­ecules into chains propagating in [011], which are cross-linked via C—H⋯π inter­actions, generating a three-dimensional network. Aromatic π–π stacking also occurs [shortest centroid–centroid separation = 3.6012 (11) Å].
PMCID: PMC3089147  PMID: 21754359
12.  Redetermination of 3-methyl­benzoic acid 
The asymmetric unit of the title compound, C8H8O2, contains two crystallographically independent mol­ecules, which form dimers linked by O⋯H—O hydrogen bonds. The benzene rings in the dimers are inclined at a dihedral angle of 7.30 (8)° and both methyl groups display rotational disorder. This redetermination results in a crystal structure with significantly higher precision than the original determination [Ellas & García-Blanco (1963 ▶). Acta Cryst. 16, 434], in which the authors reported only the unit-cell parameters and space group, without any detailed information on the atomic arrangement. In the crystal, dimers are connected by weak C—H⋯O inter­actions, forming R 2 2(10) and R 4 4(18) rings along [110] and an infinite zigzag chain of dimers along the [001] direction also occurs.
PMCID: PMC3052032  PMID: 21522332
13.  3-Carb­oxy-5-(pyridinium-4-yl)benzoate: a redetermination 
The title compound, C13H9NO4, crystallizes in a zwitterionic form with the pyridine N atom protonated and the carboxyl OH group deprotonated. The benzene and pyridinium rings are inclined with a dihedral angle of 31.42 (14)° between them. A previous report of this stucture claims, we believe incorrectly, that neither of the carboxyl­ate groups is deprotonated [Zhang et al. (2010 ▶). Acta Cryst. E66, o2928–o2928]. In the crystal, inter­molecular O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen-bonding inter­actions link adjacent mol­ecules into a three-dimensional supra­molecular network.
PMCID: PMC3120316  PMID: 21754747
14.  Crystal structure of 4,4′-bipyridine-1,1’-diium naphthalene-2,6-di­sulfonate dihydrate 
The title hydrated mol­ecular organic salt, C10H10N2 2+·C10H6O6S2 2−·2H2O, crystallized with half a bipyridinium cation, half a naphthalene-2,6-di­sulfonate anion and a water mol­ecule in the asymmetric unit. The whole cation and anion are generated by inversion symmetry, the inversion centers being at the center of the bridging C—C bond of the cation, and at the center of the fused C—C bond of the naphthalene group of the anion. In the crystal, the anions and cations stack alternately along the a axis with π–π inter­actions [inter-centroid distance = 3.491 (1) Å]. The anions are linked via O—H⋯O(sulfonate) hydrogen bonds involving two inversion-related water mol­ecules, forming chains along [10-1]. These chains are bridged by bifurcated N—H⋯(O,O) hydrogen bonds, forming a three-dimensional framework structure. There are also C—H⋯O hydrogen bonds present, reinforcing the framework structure.
PMCID: PMC4186165  PMID: 25309296
crystal structure; mol­ecular salt; bi­pyridine; nathphalenedi­sulfonate; dihydrate
15.  Crystal structures of 1,4-di­aza­bicyclo­[2.2.2]octan-1-ium 4-nitro­benzoate dihydrate and 1,4-di­aza­bicyclo­[2.2.2]octane-1,4-diium bis­(4-nitro­benzoate): the influence of solvent upon the stoichiometry of the formed salt 
Solvent-dependent outcomes are noted in co-crystallization experiments between DABCO and 4-nitrobenzoic acid with mono- and diprotonated forms of DABCO are isolated.
The 1:1 co-crystallization of 1,4-di­aza­bicyclo­[2.2.2]octane (DABCO) with 4-nitro­benzoic acid in ethanol–water (3/1) gave the salt dihydrate C6H13N2 +·C7H4NO4 −·2H2O, (1), whereas from methanol, the salt C6H14N2 2+·2C7H4NO4 −, (2), was isolated. In (1), the cation and anion are linked by a strong N—H⋯O hydrogen bond, and the carboxyl­ate anion is close to planar [dihedral angle between terminal residues = 6.83 (9)°]. In (2), a three-ion aggregate is assembled by two N—H⋯O hydrogen bonds, and the carboxyl­ate anions are again close to planar [dihedral angles between terminal residues = 1.7 (3) and 5.9 (3)°]. Through the inter­vention of solvent water mol­ecules, which self-assemble into helical supra­molecular chains along the b axis, the three-dimensional architecture in (1) is stabilized by water–DABCO O—H⋯N and water–carboxyl­ate O—H⋯O hydrogen bonds, with additional stability afforded by C—H⋯O inter­actions. The global crystal structure comprises alternating layers of water mol­ecules and ion pairs stacked along the c axis. In the crystal of (2), the three-ion aggregates are assembled into a three-dimensional architecture by a large number of methyl­ene–carboxyl­ate/nitro C—H⋯O inter­actions as well as π–π contacts between inversion-related benzene rings [inter-centroid distances = 3.5644 (16) and 3.6527 (16) Å]. The cations and anions assemble into alternating layers along the c axis.
PMCID: PMC4120614  PMID: 25161500
crystal structure; amine; carb­oxy­lic acid; co-crystallization; salt formation
16.  Redetermination of 5α-androstane-3,17-dione 
The structure of the title compound, C19H28O2, has been redermined at 295 (2) K, with much improved precision. The structure and mol­ecular packing of the title compound was first reported by Coiro et al. [Acta Cryst. (1973). B29, 1404–1409] by means of potential-energy calculations. The cell parameters in this study differ considerably in space group C2. It is a derivative of testosterone and consists of a cyclo­penta­none ring (A) fused to to successive cyclo­hexane (B and C) and cyclo­hexa­none (D) rings. The three cyclo­hexa­none rings are in slightly distorted boat configurations and the cyclo­penta­none ring is a distorted half-chair. The crystal packing is stabilized by weak inter­molecular C—H⋯O inter­actions involving O atoms from each of the cyclo­hexa­none and cyclo­penta­none rings and H atoms from each of their respective rings.
PMCID: PMC2979654  PMID: 21579576
17.  Crystal structure of lead(II) tartrate: a redetermination 
The redetermination of the crystal structure of lead tartrate from crystals grown in a gel medium confirmed the previous powder X-ray diffraction study in the space group P212121 with higher precision. Contradictions in the literature regarding space group and water content could be clarified.
Single crystals of poly[μ4-tartrato-κ6 O 1,O 3:O 1′:O 2,O 4:O 4′-lead], [Pb(C4H4O6)]n, were grown in a gel medium. In comparison with the previous structure determination of this compound from laboratory powder X-ray diffraction data [De Ridder et al. (2002 ▶). Acta Cryst. C58, m596–m598], the redetermination on the basis of single-crystal data reveals the absolute structure, all atoms with anisotropic displacement parameters and a much higher accuracy in terms of bond lengths and angles. It could be shown that a different space group or incorporation of water as reported for similarly gel-grown lead tartrate crystals is incorrect. In the structure, each Pb2+ cation is bonded to eight O atoms of five tartrate anions, while each tartrate anion links four Pb2+ cations. The resulting three-dimensional framework is stabilized by O—H⋯O hydrogen bonds between the OH groups of one tartrate anion and the carboxyl­ate O atoms of adjacent anions.
PMCID: PMC4331892
crystal structure; lead tartrate; gel growth; redetermination; O—H⋯O hydrogen bonds
18.  1,4-Dimethyl­piperazine-1,4-diium bis­(hexa­fluoro­phosphate) dihydrate 
In the title hydrated mol­ecular salt, C6H16N2 +·2PF6 −·2H2O, the complete 1,4-dimethyl­piperazine-1,4-diium dication is generated by crystallographic inversion symmetry and both C—N bonds are in equatorial orientations. In the crystal, the components are linked by O—H⋯F and N—H⋯O hydrogen bonds but there are no direct links between cations and anions.
PMCID: PMC3344619  PMID: 22590381
19.  Crystal structure of zwitterionic 3-(2-hy­droxy-2-phospho­nato-2-phosphono­eth­yl)imidazo[1,2-a]pyridin-1-ium monohydrate (minodronic acid monohydrate): a redetermination 
A redetermination of the crystal structure of minodronic acid monohydrate was carried out in order to provide accurate atomic coordinates and geometry information, whose knowledge is fundamental to elucidate the presumed polymorphism of the compound at room temperature.
In a previous study, the X-ray structure of the title compound, C9H12N2O7P2·H2O, was reported [Takeuchi et al., (1998 ▶). Chem. Pharm. Bull. 46, 1703–1709], but neither atomic coordinates nor details of the geometry were published. The structure has been redetermined with high precision as its detailed knowledge is essential to elucidate the presumed polymorphism of minodronic acid monohydrate at room temperature. The mol­ecule crystallizes in a zwitterionic form with cationic imidazolium[1,2a]pyridine and anionic phospho­nate groups. The dihedral angle formed by the planes of the pyridine and imidazole rings is 3.55 (9)°. A short intra­molecular C—H⋯O contact is present. In the crystal, mol­ecules are linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds and π–π inter­actions [centroid-to-centroid distance = 3.5822 (11) Å], forming a three-dimensional structure.
PMCID: PMC4331878
crystal structure; bis­phospho­nate; polymorphism; minodronic acid; hydrogen bonds; redetermination
20.  5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination 
The title compound, C18H21N3O3, is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007 ▶). Acta Cryst. E63, o4782–o4782]. Using the whole mol­ecule disorder, R values are much smaller than those published. An intra­molecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The dihedral angle between the mean plane of the two benzene rings (major component) is 9.0 (5)°. The crystal structure shows short C⋯C [3.189 (15)–3.298 (12) Å] and C⋯O [2.983 (5)–3.149 (13) Å] contacts. Inter­molecular C—H⋯O inter­actions link neighbouring mol­ecules into dimers with R 2 2(18) motifs. In the crystal structure, these dimers are linked together by inter­molecular C—H⋯O inter­actions into one-dimensional extended chains along the b axis. The crystal structure is further stabilized by inter­molecular π–π stacking inter­actions [centroid–centroid distances = 3.458 (8)–3.691 (6) Å].
PMCID: PMC2968344  PMID: 21581950
21.  o-Toluene­sulfonamide: a redetermination 
The structure of the title compound, C7H9NO2S, was previously determined from powder diffraction data [Tremayne, Seaton & Glidewell (2002). Acta Cryst. B58, 823–834]. It has now been refined to a significantly higher precision. The amino N-atom is bent with a C—C—S—N torsion angle of −65.8 (2)deg;. In the crystal, mol­ecules are packed into a three-dimensional framework/supramolecular structure through hydrogen bonds between the two H atoms of the sulfonamide group and sulfonyl O atoms of neighbouring mol­ecules.
PMCID: PMC2970068  PMID: 21577654
22.  1-(4-Chloro­phen­yl)piperazine-1,4-diium tetra­chlorido­zincate(II) monohydrate 
In the crystal structure of the title compound, (C10H15ClN2)[ZnCl4]·H2O, the Zn atom is coordinated by four Cl atoms in a tetrahedral geometry. The water mol­ecules and the 1-(4-chloro­phen­yl)piperazine-1,4-diium cations inter­act with the [ZnCl4]2− anions through O—H⋯Cl, N—H⋯Cl, N—H⋯O and C—H⋯Cl hydrogen bonds (five simple and one bifurcated). Inter­molecular π–π stacking inter­actions are present between adjacent aromatic rings of 1-(4-chloro­phenyl)­piperazine-1,4-diium cations (the centroid–centroid distance is 3.453 Å).
PMCID: PMC2961817  PMID: 21202751
23.  1-(2-Hy­droxy­eth­yl)-4-{3-[(E)-2-(trifluoro­meth­yl)-9H-thioxanthen-9-yl­idene]prop­yl}piperazine-1,4-diium bis­(3-carb­oxy­prop-2-enoate) 
In the title salt, C23H27F3N2OS+·2C4H3O4 −, a non-merohedral twin [ratio of the twin components = 0.402 (1):0.598 (1)], the –CF3 group is disordered over two sets of sites with occupancy factors in the ratio 0.873 (2):0.127 (2). The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit, whose thio­pyran ring has a screw-boat conformation, is 33.01 (9)°. The diprotonated piperazine ring adopts a chair conformation. In the crystal, inter­molecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds between neighboring mol­ecules form zigzag chains along the a axis and contribute to the stabilization of the packing.
PMCID: PMC3213470  PMID: 22091049
24.  1-(2-Hy­droxy­eth­yl)-4-[3-(2-trifluoro­methyl-9H-thioxanthen-9-yl­idene)prop­yl]piperazine-1,4-diium dichloride: the dihydro­chloride salt of flupentixol 
In the title compound, C23H27F3N2OS+·2Cl−, the piperazinediium ring adopts a chair conformation. The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit is 40.35 (18)°. The F atoms in the trifluoro­methyl group are disordered over two sets of sites with occupancies of 0.803 (6) and 0.197 (6). In the crystal, mol­ecules are connected by N—H⋯Cl, O—H⋯Cl C—H⋯O and C—H⋯Cl hydrogen bonds, forming chains propagating along [001]. There are also C—H⋯π inter­actions present in the crystal structure.
PMCID: PMC3213522  PMID: 22091101
25.  2-(2-Fur­yl)-1H-imidazo[4,5-f][1,10]phenanthroline-3,7-diium dichloride monohydrate 
The organic cation of the title salt, C17H12N4O2+·2Cl−·H2O, is nearly planar, the dihedral angle between two pyridine rings being 2.53 (16)° and that between the pyridinum and furan rings being 4.17 (19)°. Mol­ecules are linked via N—H⋯O, N—H⋯Cl and O—H⋯Cl hydrogen bonds, forming a three-dimensional framework and π–π stacking inter­actions help to stabilize the crystal structure [the imidazole–pyridine and imidazole–benzene centroid–centroid distances are 3.501 (3) and 3.674 (3) Å; respectively].
PMCID: PMC2968264  PMID: 21581942

Results 1-25 (99112)