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1.  1-Phenyl-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimidazole 
In the title mol­ecule, C20H13F3N2, the benzimidazole unit is close to being planar [maximum deviation = 0.012 (1) Å] and forms dihedral angles of 31.43 (7) and 61.45 (9)° with the 4-(trifluoromethyl)phenyl and 1-phenyl rings, respectively; the dihedral angle between these rings is 60.94 (10)°. In the crystal, C—H⋯F hydrogen bonds link the mol­ecules into chains along the c-axis direction. The CF3 group is rotationally disordered with an occupancy ratio of 0.557 (8):0.443 (8) for the F atoms.
doi:10.1107/S1600536813000834
PMCID: PMC3569777  PMID: 23424523
2.  1-{2-(4-Chloro­benz­yloxy)-2-[4-(mor­pho­lin-4-yl)phen­yl]eth­yl}-1H-benzimidazole propan-2-ol monosolvate 
In the title compound, C26H26ClN3O2·C3H7OH, the benzimid­azole ring system is essentially planar [maximum deviation = −0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol­ecule links with the benzimidazole ring via an O—H⋯N hydrogen bond. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R 2 2(28) motif. π–π stacking occurs between the parallel chloro­benzene rings [centroid–centroid distance = 3.792 (1) Å]. Weak C—H⋯π inter­actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.
doi:10.1107/S1600536813022599
PMCID: PMC3884486  PMID: 24427066
3.  Ethyl 1-phenyl-2-[4-(trifluoro­meth­oxy)phen­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C23H17F3N2O3, an intra­molecular C—H⋯F hydrogen bond generates an S(6) ring motif. The essentially planar 1H-benzimidazole ring system [maximum deviation = 0.021 (2) Å] forms dihedral angles of 25.00 (10) and 62.53 (11)° with the trifluoro­meth­oxy-substituted benzene and phenyl rings, respectively. The twist of the ethyl acetate group from the least-squares plane of the 1H-benzimidazole ring system is defined by a C(=O)—O—C—C torsion angle of 79.5 (3)°. In the crystal, mol­ecules are linked into a two-dimensional network parallel to the bc plane by weak C—H⋯N and C—H⋯O hydrogen bonds. Weak C—H⋯π inter­actions also observed.
doi:10.1107/S1600536812034903
PMCID: PMC3435731  PMID: 22969602
4.  (E)-4-[(4-Fluoro­benzyl­idene)amino]-3-[1-(4-isobutyl­phen­yl)eth­yl]-1-(morpholino­meth­yl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate 
In the title compound, C26H32FN5OS·0.5CH4O, the methyl group of the methanol solvent mol­ecule is disordered over two sites with equal occupancies and the solvent is further disordered about a crystallographic twofold rotation axis. The organic mol­ecule exists in a trans configuration with respect to the acyclic C=N bond. An intra­molecular C—H⋯S hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. The essentially planar 1,2,4-triazole ring [maximum deviation = 0.013 (2) Å] forms dihedral angles of 11.21 (10) and 67.53 (11)°, respectively, with the fluoro­phenyl unit and the isobutyl-substituted benzene ring. The crystal structure is stabilized by a weak inter­molecular C—H⋯π inter­action.
doi:10.1107/S1600536810015217
PMCID: PMC2979111  PMID: 21579255
5.  Crystal structure of {(E)-4-[(1-allyl-1H-1,2,3-triazol-4-yl)meth­oxy]benzyl­idene}[2-(morpholin-4-yl)eth­yl]amine 
In the title compound, C19H25N5O2, the morpholine ring has a chair conformation. The plane of the central benzene ring makes dihedral angles of 88.75 (12) and 60.02 (7)°, respectively, with the mean plane formed by the four planar C atoms of the morpholine ring and with the plane of the triazole ring. In the crystal, mol­ecules are linked via C—H⋯π inter­actions, forming slabs lying parallel to (10-1). The C atoms of the bridging ethyl­ene group, between the morpholine and benzene rings, and the terminal ethene group of the prop-1-ene substituent attached to the triazole ring, are disordered over two sets of sites, with an occupancy ratio of 0.634 (13):0.366 (13).
doi:10.1107/S1600536814016754
PMCID: PMC4186139  PMID: 25309262
crystal structure; Schiff base; morpholine; 1,2,3-triazole; disorder
6.  (R C,S Fe)-1-[3,5-Bis(trifluoro­meth­yl)phen­yl]-3-{1-[2-(diphenyl­phosphan­yl)ferro­cen­yl]eth­yl}thio­urea (unknown solvate) 
In the molecule of the the title compound, [Fe(C5H5)(C28H22F6N2PS)], the absolute configuration is R C ,SFe. The dihedral angle between the trifluoro­methyl-substituted phenyl ring and the thio­urea plane is 41.8 (9)°. The iron atom is bound to the cyclo­penta­dienyl rings in the typical η5-manner in a close to eclipsed conformation. The crystal structure features N—H⋯S hydrogen bonds, with the S atom as an acceptor for both N—H groups, forming a layered arrangement parallel to (1-10). The two –CF3 groups are each disordered over two positions with refined occupancy rates for the major components of 0.66 (7) and 0.55 (5). The crystal was grown from mixed solvents (n-hexane and ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninterpretable. The solvent contribution to the structure factors was taken into account by back-Fourier transformation of all density found in the disordered solvent area using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. The formula mass and density do not take account of the solvent.
doi:10.1107/S1600536813008453
PMCID: PMC3647794  PMID: 23723760
7.  1-{[Dimeth­yl(phen­yl)sil­yl]meth­yl}-3-(2-phenyl­eth­yl)-1H-benzimidazol-3-ium bromide monohydrate 
The title compound, C24H27N2Si+·Br−·H2O, was synthesized from 1-(dimethyl­phenyl­silylmeth­yl)-1H-benzimidazole and (2-bromo­eth­yl)benzene in dimethyl­formamide. The benzimidazole ring system is nearly planar, with a maximum deviation of 0.015 (5) Å, and forms dihedral angles of 73.0 (3) and 39.6 (2)°, with the phenyl rings. In the crystal, mol­ecules are linked by O—H⋯Br, C—H⋯Br and C—H⋯O hydrogen bonds. In addition, the structure features π–π stacking inter­actions, with a face-to-face separation of 3.644 (3) Å between parallel benzimidazole ring systems.
doi:10.1107/S1600536812034915
PMCID: PMC3435733  PMID: 22969604
8.  Ethyl 2-[4-(morpholin-4-yl)phen­yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-1,3-benzimidazole-5-carboxyl­ate monohydrate 
The asymmetric unit of the title compound, C27H32N4O4·H2O, contains two independent benzimidazole-5-carboxyl­ate mol­ecules and two water mol­ecules. In both main mol­ecules, the pyrrolidine rings are in an envelope conformation with a methyl­ene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one mol­ecule, an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds connect pairs of main mol­ecules and pairs of water mol­ecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H⋯O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H⋯π interactions.
doi:10.1107/S1600536812039268
PMCID: PMC3470336  PMID: 23125749
9.  1-[2-Oxo-5-(trifluoro­meth­oxy)indolin-3-yl­idene]-4-[4-(trifluoro­methyl)­phen­yl]thio­semicarbazide 
In the title compound, C17H10F6N4O2S, an intra­molecular N—H⋯N hydrogen bonds forms an S(5) ring whereas N—H⋯O and C—H⋯S inter­actions complete S(6) ring motifs. The dihedral angle between the fused ring system and the phenyl ring is 6.68 (8)°. In the crystal, the mol­ecules are dimerized due to N—H⋯O inter­actions. π–π inter­actions are present between the benzene rings [centroid–centroid distance = 3.6913 (15) Å] and between the five membered ring and the trifluoro­meth­yl)phenyl ring [centroids–centroid distance = 3.7827 (16) Å]. One of the trifluoro­meth­oxy F atoms is disordered over two sites with occupancy ratio of 0.76 (3):0.24 (3). The F atoms of the p-trifluoro­methyl substituent are disordered over three sets of sites with an occupancy ratio of 0.70 (2):0.152 (11):0.147 (13).
doi:10.1107/S1600536810023494
PMCID: PMC3006819  PMID: 21587965
10.  1-{2-Phenyl-2-[4-(trifluoro­meth­yl)­benzyl­oxy]eth­yl}-1H-benzimidazole 
The asymmetric unit of the crystal structure of the title compound, C23H19F3N2O, contains two independent mol­ecules. In the two mol­ecules the planar benzimidazole ring systems are oriented with respect to the phen­yl/trifluoro­methyl­benzene rings at dihedral angles of 9.62 (6)/78.63 (7) and 2.53 (8)/83.83 (9)°. In the crystal structure, inter­molecular C—H⋯N hydrogen bonds link the mol­ecules into R 2 2(6) dimers. The mol­ecules are elongated along [001] and stacked along the b axis.
doi:10.1107/S1600536808024033
PMCID: PMC2962243  PMID: 21203341
11.  4-(4-Bromo­benzyl­ideneamino)-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1-(mor­phol­ino­meth­yl)-1H-1,2,4-triazole-5(4H)-thione 
There are two mol­ecules (A and B) in the asymmetric unit of the title compound, C26H32BrN5OS, with almost identical geometry. The morpholine ring adopts the usual chair conformation in both mol­ecules. The triazole ring forms dihedral angles of 4.84 (6) and 74.19 (6)°, respectively, with the bromo­phenyl and isobutylbenzene rings in mol­ecule A, and angles of 16.68 (7) and 87.29 (6)°, respectively, in mol­ecule B. Intra­molecular C—H⋯S hydrogen bonds generate S(5) and S(6) ring motifs in both independent mol­ecules. The crystal structure is stabilized by C—H⋯N, C—H⋯Br and C—H⋯O hydrogen-bonding inter­actions, together with C—H⋯π inter­actions.
doi:10.1107/S160053680802254X
PMCID: PMC2962191  PMID: 21203272
12.  3-(2,4-Dichloro­phen­yl)-5-(4-fluoro­phen­yl)-2-phenyl-7-(trifluoro­meth­yl)pyrazolo­[1,5-a]pyrimidine 
In the title compound, C25H13Cl2F4N3, there are four planar systems, viz. three benzene rings and a pyrazolo­[1,5-a]pyrim­idine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichloro­phenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluoro­phenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals inter­actions. A Cl⋯Cl inter­action of 3.475 (3) Å also occurs.
doi:10.1107/S1600536812023641
PMCID: PMC3379478  PMID: 22719676
13.  3-Meth­oxy-2-[2-({[6-(trifluoro­meth­yl)pyridin-2-yl]­oxy}meth­yl)phen­yl]prop-2-enoic acid 
The title mol­ecule, C17H14F3NO4, consists of two nearly planar fragments, viz. the 2-benzyl­oxypyridine (r.m.s. deviation 0.016 Å) and (E)-3-meth­oxy­prop2-enoic (r.m.s. deviation 0.004 Å) units, which form a dihedral angle of 84.19 (7)°. In the crystal, pairs of O—H⋯O hydrogen bonds link mol­ecules into dimers that are further connected by C—H⋯O and C—H⋯F inter­actions into (001) layers. In addition, π–π stacking inter­actions are observed within a layer between the pyridine and benzene rings [centroid–centroid distance = 3.768 (2) Å]. The F atoms of the trifluoro­methyl group are disordered over two sets of sites in a 0.53 (4):0.47 (4) ratio.
doi:10.1107/S1600536812042316
PMCID: PMC3515258  PMID: 23284478
14.  4-(Morpholin-4-yl)-3-(trifluoro­meth­yl)­benzonitrile 
In the title benzonitrile compound, C12H11F3N2O, an intra­molecular C—H⋯F hydrogen bond generates an S(7) ring motif. The trifluoro­methyl group is disordered over two orientations with a refined occupancy ratio of 0.549 (16):0.451 (16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04 (10)° with each other. In the crystal, mol­ecules are connected by inter­molecular C—H⋯F and C—H⋯O inter­actions to form R 2 2(8) ring motifs. These inter­actions also link the mol­ecules into chains parallel to the [10] direction.
doi:10.1107/S1600536811020666
PMCID: PMC3151857  PMID: 21837008
15.  Ethyl 1-(2-hy­droxy­eth­yl)-2-(4-meth­oxy­phen­yl)-1H-benzimidazole-5-carboxyl­ate monohydrate 
In the title mol­ecule, C19H20N2O4·H2O, the benzimidazole ring system is essentially planar [maximum deviation = 0.013 (11) Å] and is inclined to the 4-meth­oxy­phenyl ring by 30.98 (5)°. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds involving the water mol­ecule link neighbouring mol­ecules, forming a two-dimensional network lying parallel to the bc plane. There are also C—H⋯π and π–π inter­actions present. The latter involve inversion-related benzimidazole rings with centroid–centroid distances of 3.5552 (8) and 3.7466 (8) Å.
doi:10.1107/S1600536812001262
PMCID: PMC3275179  PMID: 22347035
16.  3-[Hy­droxy(3-meth­oxy­phen­yl)methyl­idene]-2-(2-oxo-2-phenyl­eth­yl)-3,4-dihydro-2H-1λ6,2-benzothia­zine-1,1,4-trione 
In the title mol­ecule, C24H19NO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zine unit and the meth­oxy­phenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2)°, while the benzene ring of the 2-oxo-2-phenyl­ethyl group is inclined at 79.68 (11) and 81.01 (10)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions, and the crystal packing is stabilized by weak C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009002
PMCID: PMC3343951  PMID: 22590032
17.  N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]-2-eth­oxy­benzamide 
In the title compound, C17H13F3N2O2, the two aromatic rings are essentially coplanar, forming a dihedral angle of 2.78 (12)°. The non-H atoms of the eth­oxy group are coplanar with the attached ring [maximum deviation = 0.271 (3) Å]. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal structure, mol­ecules are linked by inter­molecular C—H⋯N and C—H⋯F hydrogen bonds.
doi:10.1107/S1600536810019811
PMCID: PMC3006830  PMID: 21587782
18.  Ethyl 1-(2-hy­droxy­eth­yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C19H20N2O3, contains two mol­ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl­ate groups. Intra­molecular C—H⋯O hydrogen bonds generate S(8) ring motifs in both mol­ecules A and B. In each mol­ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023 (1) and 0.020 (1) Å, respectively, for mol­ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34 (5)° for mol­ecule A and 42.42 (5)° for mol­ecule B. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into [100] columns with a cross-section of two-mol­ecule by two-mol­ecule wide, and further stabilization is provided by weak C—H⋯π and π–π inter­actions [centroid separations = 3.5207 (7) and 3.6314 (8) Å].
doi:10.1107/S1600536810020799
PMCID: PMC3006903  PMID: 21587829
19.  2-(Naphthalen-1-yl)-1-phenyl-1H-benzimid­azole benzene hemisolvate 
In the title compound, C23H16N2·0.5C6H6, the benzimidazole unit [maximum deviation = 0.0258 (6) Å] and the naphthalene ring system [maximum deviation = 0.0254 (6) Å] are both essentially planar and make a dihedral angle of 61.955 (17)°. The imidazole ring makes dihedral angle of 61.73 (4)° with the phenyl ring. An intra­molecular C—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, seven weak C—H⋯π inter­actions involving the fused ring system, the benzene solvent mol­ecule, the imidazole phenyl rings are observed, leading to a three-dimensional architecture.
doi:10.1107/S160053681303331X
PMCID: PMC3914093  PMID: 24526997
20.  2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro­meth­yl)phen­yl]-1,4,5,6,7,8-hexa­hydro­quinoline-3-carbonitrile 
In the title mol­ecule, C19H18F3N3O, the dihydro­pyridine and cyclo­hexene rings both adopt sofa conformations. The five essentially planar atoms of the dihydro­pyridine ring [maximum deviation = 0.039 (2) Å] form a dihedral angle of 88.19 (8)° with the benzene ring. The F atoms of the trifluoro­methyl group were refined as disordered over two sets of sites in a 0.840 (3):0.160 (3) ratio. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link mol­ecules into a two-dimensional network parallel to (100).
doi:10.1107/S1600536812050684
PMCID: PMC3588344  PMID: 23476367
21.  2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro­meth­yl)phen­yl]-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile 
In the title mol­ecule, C19H17F3N2O2, the fused cyclo­hexene and pyran rings adopt sofa and flattened boat conformations, respectively. The four essentially planar atoms of the pyran ring [maximum deviation = 0.008 (2) Å] form a dihedral angle of 88.13 (9)° with the benzene ring. The F atoms of the trifluoro­methyl group were refined as disordered over three sets of sites in a 0.507 (7):0.330 (7):0.163 (3) ratio. In the crystal, mol­ecules are connected into inversion dimers via pairs of N—H⋯N hydrogen bonds and these dimers are further linked by N—H⋯O hydrogen bonds into a two-dimensional network parallel to (100).
doi:10.1107/S1600536813004522
PMCID: PMC3588544  PMID: 23476593
22.  4′-[2-(Trifluoro­meth­yl)phen­yl]-2,2′:6′,2′′-terpyridine 
The title compound, C22H14F3N3, is a versatile tridentate N-donor ligand consisting of a terpyridyl (terpy) molecule substituted in the 4′-position by a phenyl group, itself substituted in an ortho-position by a bulky trifluoro­methyl group. The phenyl ring is twisted as a result of steric inter­actions involving the bulky trifluoro­methyl substituent. This is reflected in the dihedral angle between the mean plane through the C atoms of the phenyl ring and the terpyridyl unit being 69.2 (1)°. The crystal structure contains no short van der Waals contacts. However, the terpy units stack in a head-to-tail orientation perpendicular to the c axis. The structure is is loosely stabilized by π–π inter­actions between the terminal pyridine rings of adjacent mol­ecules along the stack. The perpendicular distance between the mean planes through the terpy moieties of adjacent mol­ecules is 3.4 (1) Å.
doi:10.1107/S1600536809002384
PMCID: PMC2968217  PMID: 21581974
23.  Crystal structure of (E)-1(anthracen-9-ylmethylidene)[2-(morpholin-4-yl)eth­yl]amine 
The title compound, C21H22N2O, crystallizes with two independent mol­ecules in the asymmetric unit. In both mol­ecules, the anthracene ring systems are almost planar, with maximum deviations of 0.071 (8) and 0.028 (7) Å, and make dihedral angles of 73.4 (2) and 73.3 (2)° with the least-squares planes formed by the four C atoms of the morpholine rings, which adopt a chair conformation. An intra­molecular C—H⋯π inter­action occurs. In the crystal, the packing is stabilized by weak C—H⋯O hydrogen bonds, which connect pairs of molecules into parallel to the c axis, and C—H⋯π inter­actions.
doi:10.1107/S1600536814018807
PMCID: PMC4186061  PMID: 25309217
crystal structure; C—H⋯π inter­actions; Schiff bases; anthracene; morpholine; methanimine
24.  5-Chloro-N-{4-oxo-2-[4-(trifluoro­meth­yl)phen­yl]-1,3-thia­zolidin-3-yl}-3-phenyl-1H-indole-2-carboxamide 
In the title compound, C25H17ClF3N3O2S, the five-membered 1,3-thia­zolidine ring adopts a twist conformation. The three F atoms of the CF3 group are disordered over two sets of sites with refined occupancies of 0.542 (18) and 0.458 (18). In the nine-membered 1H-indoline ring system, the 1H-pyrrole ring forms a dihedral angle of 4.7 (2)° with the benzene ring, while it is twisted at an angle of 46.5 (2)° with respect to the attached phenyl ring. The dihedral angle between the phenyl and trifluoro­methyl-substituted benzene rings is 56.0 (2)°. In the crystal, N—H⋯O hydrogen bonds connect the mol­ecules into a three-dimensional network. In addition, weak C—H⋯O hydrogen bonds and weak C—H⋯π inter­actions are observed.
doi:10.1107/S1600536812039347
PMCID: PMC3470337  PMID: 23125750
25.  3-Chloro-6-{4-[3-(trifluoro­meth­yl)phen­yl]piperazin-1-yl}pyridazine 
The title compound, C15H14ClF3N4, was synthesized from 3,6-dichloro­pyridazine and 1-[3-(trifluoro­meth­yl)phen­yl]piper­azine. The piperazine ring is flanked by 3-chloro­pyridazine and 3-trifluoro­methyl­phenyl rings and adopts a chair conformation, whereas the 3-chloro­pyridazine and 3-trifluoro­methyl­phenyl rings are planar, with maximum deviations of 0.0069 (13) and 0.0133 (14) Å, respectively. The crystal structure is stabilized by weak inter­molecular C—H⋯N hydrogen-bond inter­actions.
doi:10.1107/S1600536810004137
PMCID: PMC2983628  PMID: 21580304

Results 1-25 (87268)