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1.  Crystal structure of 1-(3-chloro­phen­yl)piperazin-1-ium picrate–picric acid (2/1) 
The title salt {systematic name: bis­[1-(3-chloro­phen­yl)piperazinium 2,4,6-tri­nitro­phenolate]–picric acid (2/1)}, 2C10H14ClN2 +·2C6H5N3O7 −·C6H6N3O7, crystallized with two independent 1-(3-chloro­phen­yl)piperazinium cations, two picrate anions and a picric acid mol­ecule in the asymmetric unit. The six-membered piperazine ring in each cation adopts a slightly distorted chair conformation and contains a protonated N atom. In the picric acid mol­ecule, the mean planes of the nitro groups in the ortho-, meta-, and para-positions are twisted from the benzene ring by 31.5 (3), 7.7 (1), and 3.8 (2)°, respectively. In the anions, the dihedral angles between the benzene ring and the ortho-, meta-, and para-nitro groups are 36.7 (1), 5.0 (6), 4.8 (2)°, and 34.4 (9), 15.3 (8), 4.5 (1)°, respectively. The nitro group in one anion is disordered and was modeled with two sites for one O atom with an occupancy ratio of 0.627 (7):0.373 (7). In the crystal, the picric acid mol­ecule inter­acts with the picrate anion through a trifurcated O—H⋯O four-centre hydrogen bond involving an intra­molecular O—H⋯O hydrogen bond and a weak C—H⋯O inter­action. Weak inter­molecular C—H⋯O inter­actions are responsible for the formation of cation–anion–cation trimers resulting in a chain along [010]. In addition, weak C—H⋯Cl and weak π–π inter­actions [centroid–centroid distances of 3.532 (3), 3.756 (4) and 3.705 (3) Å] are observed and contribute to the stability of the crystal packing.
doi:10.1107/S1600536814023654
PMCID: PMC4257327  PMID: 25484834
crystal structure; piperazin-1-ium; picrate; picric acid; salt
2.  Crystal structures of 4-(pyrimidin-2-yl)piperazin-1-ium chloride and 4-(pyrimidin-2-yl)piperazin-1-ium nitrate 
The title salts, C8H13N4 +·Cl−, (I), and C8H13N4 +·NO3 −, (II), contain linked pyridinium–piperazine heterocycles. In the crystal of (I), weak N—H⋯Cl inter­actions lead to zigzag chains along [100] while in the crystal of (II), bifurcated N—H⋯(O,O) hydrogen bonds and weak C—H⋯O inter­actions collectively link the components into infinite chains along [100].
The title salts, C8H13N4 +·Cl−, (I), and C8H13N4 +·NO3 −, (II), contain linked pyridinium–piperazine heterocycles. In both salts, the piperazine ring adopts a chair conformation with protonation at the N atom not linked to the other ring. In the crystal of (I), weak N—H⋯Cl inter­actions are observed, leading to zigzag chains along [100]. In the crystal of (II), both H atoms on the NH2 + group form bifurcated N—H⋯(O,O) hydrogen bonds. Weak C—H⋯O inter­actions are also observed. These bonds collectively link the components into infinite chains along [100].
doi:10.1107/S1600536814020169
PMCID: PMC4257175  PMID: 25484652
crystal structure; pyrimidine–piperazine heterocyclic salts; chloride salt; nitrate salt; bifurcated hydrogen bonds
3.  Crystal structure of 3-[4-(pyrimidin-2-yl)piperazin-1-ium-1-yl]butano­ate 
The title compound, C12H18N4O2, crystallizes in the zwitterionic form with protonation at the N atom of the piperazine ring bearing the carboxylate group. The piperazine ring adopts a slightly distorted chair conformation. In the crystal, N—H⋯O hydrogen bonds are observed, forming chains along [010]. The packing is consolidated by C—H⋯O inter­actions, which generate a three-dimensional network.
doi:10.1107/S1600536814018972
PMCID: PMC4186175  PMID: 25309227
crystal structure; 3-(piperazin-1-ium-1-yl)butano­ate; zwitterionic form; fused heterocyclic derivatives; aza-Michael reactions
4.  Crystal structure of N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-2-[(E)-(2-hy­droxy­benzyl­idene)amino]­acetamide 
In the title compound, C22H19ClN2O3S, the dihedral angle between the mean planes of the thio­phene ring and the chloro­phenyl and hy­droxy­phenyl rings are 70.1 (1) and 40.2 (4)°, respectively. The benzene rings are twisted with respect to each other by 88.9 (3)°. The imine bond lies in an E conformation. Intra­molecular O—H⋯N and N—H⋯O hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C—H⋯O inter­actions link the mol­ecules, forming chains along the c axis and zigzag chains along the b axis, generating sheets lying parallel to (100).
doi:10.1107/S1600536814018224
PMCID: PMC4186110  PMID: 25309197
crystal structure; thio­phene derivatives; Schiff bases; hydrogen bonding
5.  Two tautomers in the same crystal: 3-(4-fluoro­phen­yl)-1H-pyrazole and 5-(4-fluoro­phen­yl)-1H-pyrazole 
The title co-crystal, 3-(4-fluoro­phen­yl)-1H-pyrazole–5-(4-fluoro­phen­yl)-1H-pyrazole (1/1), C9H7FN2, crystallizes with four independent mol­ecules (A, B, C and D) in the asymmetric unit exhibiting two tautomeric forms (A and D; B and C) due to N—H proton exchange between the two N atoms of the pyrazole ring. The dihedral angles between the mean planes of the pyrazole and benzene rings are 15.6 (1), 19.8 (9), 14.0 (1) and 10.7 (7)° in mol­ecules A, B, C and D, respectively. In the crystal, N—H⋯N hydrogen bonds link the four mol­ecules in the asymmetric unit into a ring with an R 4 4(12) motif. Furthermore, weak C—H⋯F inter­actions link the mol­ecules into a three-dimensional network.
doi:10.1107/S160053681401695X
PMCID: PMC4186127  PMID: 25309273
crystal structure; pyrazole derivative; tautomeric forms; hydrogen bonds
6.  Crystal structure of N-(3-benzoyl-4,5,6,7-tetra­hydro-1-benzo­thio­phen-2-yl)benzamide 
In the title compound, C22H19NO2S, the cyclo­hexene ring adopts a half-chair conformation. The dihedral angles between the plane of the thio­phene ring and those of its amide- and carbonyl-bonded benzene rings are 7.1 (1) and 59.0 (2)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, very weak aromatic π–π stacking inter­actions [centroid–centroid separation = 3.9009 (10) Å] are observed.
doi:10.1107/S1600536814016948
PMCID: PMC4186148  PMID: 25309274
crystal structure; hydrogen bonding; π–π stacking inter­actions; benzamide; 1-benzo­thio­phene; 2-amino­thio­phene derivatives
7.  (2E)-1-(4-Chloro­phen­yl)-3-[4-(propan-2-yl)phen­yl]prop-2-en-1-one 
In the title compound, C18H17ClO, the dihedral angle between the benzene rings is 53.5 (1)°. The mean plane of the prop-2-en-1-one group is twisted by 24.5 (8) and 33.5 (3)° from the chloro- and propanyl-substituted rings, respectively.
doi:10.1107/S1600536814015281
PMCID: PMC4158522  PMID: 25249906
crystal structure
8.  1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone 
In the title compound, C20H21ClN2O, the dihedral angles between the pyrazole ring (r.m.s. deviation = 0.049 Å) and the benzene and chloro­benzene rings are 84.65 (10) and 3.35 (10)°, respectively. In the crystal, inversion dimers linked by pairs of weak C—H⋯O inter­actions generate R 2 2(16) loops. Weak π–π stacking inter­actions [centroid–centroid distance = 3.8490 (11) Å] are also observed.
doi:10.1107/S1600536814013348
PMCID: PMC4120582  PMID: 25161567
9.  4-[(4-Bromo­phenyl)amino]-2-methyl­idene-4-oxo­butanoic acid 
In the title compound, C11H10BrNO3, two independent mol­ecules (A and B) crystallize in the asymmetric unit. The dihedral angles between the mean planes of the 4-bromo­phenyl ring and amide group are 24.8 (7) in mol­ecule A and 77.1 (6)° in mol­ecule B. The mean plane of the methyl­idene group is further inclined by 75.6 (4) in mol­ecule A and 72.5 (6)° in mol­ecule B from that of the amide group. In the crystal, N—H⋯O hydrogen bonds formed by amide groups and O—H⋯O hydrogen bonds formed by carb­oxy­lic acid groups are observed and supported additionally by weak C—H⋯O inter­actions between the methyl­idene and amide groups. Together, these link the mol­ecules into chains of dimers along [110] and form R 2 2(8) graph-set motifs.
doi:10.1107/S1600536814012872
PMCID: PMC4120590  PMID: 25161566
10.  1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}butan-1-one 
In the title compound, C22H25ClN2O, the pyrazole ring exhibits an envelope conformation with the methine C atom as the flap. The benzene rings are twisted by 3.3 (5) and 84.6 (5)° from the pyrazole mean plane, and are inclined to each other by 81.4 (4)°. In the crystal, pairs of weak C—H⋯O hydrogen bonds form centrosymmetric dimers with an R 2 2(16) graph-set motif. C—H⋯π inter­actions link the dimers into columns propagating in [100].
doi:10.1107/S1600536814013063
PMCID: PMC4120539  PMID: 25161554
11.  1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}propan-1-one 
In the title compound, C21H23ClN2O, the dihedral angle between the benzene rings is 83.2 (6)°, while the mean plane of the pyrazole ring [r.m.s. deviation = 0.043 (1) Å] makes dihedral angles of 3.4 (3) and 86.2 (1)° with the benzene rings. In the crystal, a pair of weak C—H⋯O inter­actions between the benzene ring and the propan-1-one group link the mol­ecules into an inversion dimer with an R 2 2(16) graph-set motif. In addition, a weak π–π stacking inter­action [centroid–centroid distance = 3.959 (4) Å] connects the dimers into a tape running along [201].
doi:10.1107/S1600536814013075
PMCID: PMC4120579  PMID: 25161555
12.  4-[(4-Acetyl­phen­yl)amino]-2-methyl­idene-4-oxo­butanoic acid 
In the title compound, C13H13NO4, the N—C(=O) bond length of 1.354 (2) Å is indicative of amide-type resonance. The dihedral angle between the mean planes of the benzene ring and oxo­amine group is 36.4 (3)°, while the mean plane of the 2-methyl­idene group is inclined by 84.2 (01)° from that of the oxo­amine group. In the crystal, classical O—H⋯O hydrogen bonds formed by the carb­oxy­lic acid groups and weak N—H⋯O weak inter­actions formed by the amide groups and supported by weak C—H⋯O inter­actions between the 2-methyl­idene, phenyl and acetyl groups with the carb­oxy­lic acid, oxo­amine and acetyl O atoms, together link the mol­ecules into dimeric chains along [010]. The O—H⋯O hydrogen bonds form R 2 2(8) graph-set motifs.
doi:10.1107/S1600536814012562
PMCID: PMC4120591  PMID: 25161547
13.  {2-[(4-Nitro­benzyl­idene)amino]-4,5,6,7-tetrahydro-1-benzo­thio­phen-3-yl}(phen­yl)methanone 
In the title compound, C22H18N2O3S, disorder is found in the benzoyl group (A and B), as well as for four C atoms of the cyclo­hexene ring. Two orientations were modeled in a 0.583 (5):0.417 (5) ratio. The cyclo­hexene ring is in a distorted chair conformation. The dihedral angles between the mean plane of the thio­phene ring and the 4-nitro­benzene and phenyl rings are 30.9 (8) and 64.8 (3) (A) and 62.4 (7)° (B). The mean planes of the 4-nitro­benzene and the phenyl rings are almost perpendicular to each other, with dihedral angles of 85.4 (1) (A) and 83.9 (8)° (B). An extensive array of weak C—H⋯O inter­actions consolidate mol­ecules into a three-dimensional architecture, forming chains along [001] and [010] and layers parallel to (011).
doi:10.1107/S1600536814012185
PMCID: PMC4051066  PMID: 24940302
14.  N-Ethyl-2-[1-(2-hy­droxy-4-methyl­phen­yl)ethyl­idene]hydrazinecarbo­thio­amide 
The title compound, C12H17N3OS, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the benzene ring and the hydrazinecarbo­thio­amide group are 6.9 (4) and 37.2 (5)° in mol­ecules A and B, respectively. An intra­molecular O—H⋯N hydrogen bond is observed in each mol­ecule. This serves to maintain an approximately planar conformation for mol­ecule A, but leaves a significant twist between these two groups in mol­ecule B. In the crystal, a weak N—H⋯S inter­action is observed, forming inversion dimers among the B mol­ecules and resulting in an R 2 2(8) motif. These dimers are further inter­connected by weak N—H⋯O and C—H⋯O inter­molecular inter­actions, forming chains along [011].
doi:10.1107/S1600536814012203
PMCID: PMC4051077  PMID: 24940300
15.  N-Ethyl-2-[1-(2-hy­droxy­naphthalen-1-yl)ethyl­idene]hydrazinecarbo­thio­amide 
In the title compound, C15H17N3OS, the dihedral angle between the mean planes of the 2-hy­droxy­napthyl ring system and the hydrazinecarbo­thio­amide group is 73.7 (3)°. In the crystal, weak O—H⋯S and C—H⋯O inter­actions and π–π stacking inter­actions involving one of the hy­droxy­napthyl rings with a centroid–centroid distance of 3.6648 (14) Å are observed, forming infinite chains along [010]. In addition, N—H⋯S inter­actions occur.
doi:10.1107/S1600536814012057
PMCID: PMC4051082  PMID: 24940298
16.  4-Acetyl­piperazinium picrate 
In the title salt, C6H13N2O+·C6H2N3O7 − (systematic name: 4-acetyl­piperazin-1-ium 2,4,6-tri­nitro­phenolate), the piperazin-1-ium ring has a slightly distorted chair conformation. In the picrate anion, the mean planes of the two o-NO2 and p-NO2 groups are twisted with respect to the benzene ring by 15.0 (2), 68.9 (4) and 4.4 (3)°, respectively. In the crystal, N—H⋯O hydrogen bonds are observed, linking the ions into an infinite chain along [010]. In addition, weak cation–anion C—H⋯O inter­molecular inter­actions and a weak π–π stacking inter­action between the benzene rings of the anions, with an inter-centroid distance of 3.771 (8) Å, help to stabilize the crystal packing, giving an overall sheet structure lying parallel to (100). Disorder was modelled for one of the O atoms in one of the o-NO2 groups over two sites with an occupancy ratio of 0.57 (6):0.43 (6).
doi:10.1107/S1600536814011726
PMCID: PMC4051097  PMID: 24940287
17.  4-[(E)-(4-Hy­droxy­benzyl­idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione 
The title compound, C10H10N4OS, is nearly planar with the mean planes of the hy­droxy­benzyl and triazole rings inclined at an angle of only 3.2 (7)°. In the crystal, O—H⋯N hydrogen bonds between the hy­droxy group and the triazole ring in concert with weak N—H⋯S inter­molecular inter­actions between the triazole ring and thione group form chains along [-210] enclosing R 2 2(8) graph-set motifs. A weak intra­molecular C—H⋯S inter­action and inter­molecular π–π inter­actions [centroid–centroid distance = 3.5990 (15) Å] are also observed.
doi:10.1107/S1600536814012215
PMCID: PMC4051099  PMID: 24940299
18.  3-(4-Fluoro­benzo­yl)-4-(4-fluoro­phen­yl)-4-hy­droxy-2,6-di­phenyl­cyclo­hexane-1,1-dicarbo­nitrile 
In the title compound, C33H24F2N2O2, the cyclo­hexane ring adopts a slightly distorted chair conformation. The dihedral angle between the planes of the phenyl rings is 71.80 (9)°, while the planes of the fluoro­phenyl and fluoro­benzoyl rings are inclined to one another by 31.04 (10)°. The dihedral angles between the planes of the phenyl ring adjacent to the 4-hydroxy group and those of the the fluoro­phenyl and fluoro­benzoyl rings are 51.64 (10) and 34.31 (10)°, respectively, while the corresponding angles for the phenyl ring adjacent to the 3-(4-fluorobenzoyl) group are 57.51 (9) and 85.02 (10)°, respectively. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked via pairs of O—H⋯N hydrogen bonds, forming inversion dimers. The dimers are linked via C—H⋯N and C—H⋯O hydrogen bonds, forming chains along the c-axis direction. C—H⋯F hydrogen bonds link the chains into sheets lying parallel to the bc plane.
doi:10.1107/S1600536814012197
PMCID: PMC4051101  PMID: 24940301
19.  2-(2-Methyl­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide 
In the title compound, C12H12N2OS, the dihedral angle between the benzene and thia­zole rings is 83.5 (7)°. The acetamide group is almost coplanar with the thia­zole ring, being twisted from it by 4.2 (9)°. In the crystal, pairs of N—H⋯N hydrogen bonds link mol­ecules into inversion dimers, generating R 2 2[8] loops; the dimers are stacked along [001].
doi:10.1107/S1600536814011684
PMCID: PMC4051114  PMID: 24940286
20.  4-(Pyrimidin-2-yl)piperazin-1-ium (E)-3-carb­oxy­prop-2-enoate 
In the cation of the title salt, C8H13N4 +·C4H3O4 −, the piperazinium ring adopts a slightly distorteded chair conformation. In the crystal, a single strong O—H⋯O inter­molecular hydrogen bond links the anions, forming chains along the c-axis direction. The chains of anions are linked by the cations, via N—H⋯O hydrogen bonds, forming sheets parallel to (100). These layers are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional structure. In addition, there are weak π–π inter­actions [centroid–centroid distance = 3.820 (9) Å] present involving inversion-related pyrimidine rings.
doi:10.1107/S1600536814011489
PMCID: PMC4051061  PMID: 24940275
21.  4-(Furan-2-carbon­yl)piperazin-1-ium 3,5-di­nitro­benzoate 
In the cation of the title salt, C9H13N2O2 +·C7H3N2O6 −, the piperazine ring adopts a slightly distorted chair conformation. Twofold rotational disorder is exhibited by the furan ring in a 0.430 (4):0.570 (4) ratio. In the crystal, N—H⋯O hydrogen bonds link the ions into chains along [010]. Additional weak C—H⋯O inter­actions are observed, leading to a supra­molecular layer parallel to (011).
doi:10.1107/S160053681401126X
PMCID: PMC4051063  PMID: 24940274
22.  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.
doi:10.1107/S1600536814011064
PMCID: PMC4051083  PMID: 24940270
23.  Pyrimethaminium 2-{[4-(tri­fluoro­meth­yl)phen­yl]sulfan­yl}benzoate dimethyl sulfoxide monosolvate 
In the cation of the title solvated mol­ecular salt, C12H14ClN4 +·C14H8F3O2S−·C2H6OS [systematic name of the cation: 2,4-di­amino-5-(4-chloro­phen­yl)-6-ethyl­pyrimidin-1-ium], the dihedral angle between the planes of the pyrimidinium and 4-chloro­phenyl rings is 77.2 (5)°. In the anion, the planes of the benzene rings are twisted with respect to each other by 71.5 (5)°. Disorder was modelled for the dimethyl sulfoxide solvent mol­ecule over two set of sites in a 0.7487 (13):0.2513 (13) ratio. In the crystal, the cations are linked by inversion-generated pairs of N—H⋯N hydrogen bonds, with an R 2 2(8) graph-set motif. The cation donates two N—H⋯O hydrogen bonds to the anion, also generating an R 2 2(8) loop. These inter­actions, along with cation–solvent N—H⋯O hydrogen bonds, and cation–anion C—H⋯F, solvent–anion C—H⋯O and C—H⋯F inter­actions, result in a three-dimensional network.
doi:10.1107/S1600536814010411
PMCID: PMC4051059  PMID: 24940262
24.  Flunarizinium isonicotinate 
In the cation of the title salt {systematic name: 4-[bis­(4-fluoro­phen­yl)meth­yl]-1-[(2E)-3-phenyl­prop-2-en-1-yl]piperazin-1-ium pyridine-4-carboxyl­ate}, C26H27F2N2 +·C6H4NO2 −, the piperazine ring is in a slightly distorted chair conformation. The dihedral angle between the mean planes of the fluoro-substituted benzene rings is 81.9 (1)° and these benzene rings form dihedral angles of 6.5 (1) and 87.8 (1)° with the phenyl ring. In the crystal, a single N—H⋯O hydrogen bond links the cation and the anion. In addition, weak C—H⋯O hydrogen bonds and π–π stacking inter­actions involving one of the fluoro-substituted benzene rings and the phenyl ring, with a centroid–centroid distance of 3.700 (7) Å, link mol­ecules along [100].
doi:10.1107/S1600536814010423
PMCID: PMC4051108  PMID: 24940261
25.  N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)-2-(4-nitro­phen­yl)acetamide 
In the title compound, C19H18N4O4, the nitro­phenyl and phenyl rings are twisted by 67.0 (6) and 37.4 (4)°, respectively, with respect to the pyrazole ring plane [maximum deviation = 0.0042 (16) Å]. The dihedral angle between the mean planes of the phenyl rings is 59.3 (3)°. The amide group, with a C—N—C—C torsion angle of 177.54 (13)°, is twisted away from the plane of the pyrazole ring in an anti­periplanar conformation. In the crystal, N—H⋯O hydrogen bonds involving the carbonyl group on the pyrazole ring and the amide group, together with weak C—H⋯O inter­actions forming R 2 2(10) graph-set motifs, link the mol­ecules into chains along [100]. Additional weak C—H⋯O inter­actions involving the nitro­phenyl rings further link the mol­ecules along [001], also forming R 2 2(10) graph-set motifs, thereby generating (010) layers.
doi:10.1107/S1600536814009738
PMCID: PMC4051092  PMID: 24940224

Results 1-25 (248)