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1.  Ethyl 2-(4-hy­droxy-3-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate 
In the title compound, C24H27N3O5·H2O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intra­molecular C—H⋯π inter­action is observed. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and C—H⋯O inter­actions.
doi:10.1107/S1600536811052391
PMCID: PMC3254439  PMID: 22259586
2.  Ethyl 2-(4-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C24H27N3O4, contains two mol­ecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Å in A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for mol­ecule A and 51.40 (5) ° for mol­ecule B. In both mol­ecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C—H⋯O inter­actions link the mol­ecules, generating [100] chains. The crystal packing also features weak π–π inter­actions between the imidazole and benzene rings [centroid–centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid–centroid distance = 3.7001 (7) Å] and C—H⋯π inter­actions involving the benzene rings.
doi:10.1107/S1600536811055966
PMCID: PMC3275001  PMID: 22346946
3.  Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C28H27FN4O3·H2O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methyl­ene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H⋯O and O—H⋯N hydrogen bonds and a π–π inter­action between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H⋯O and C—H⋯F inter­actions.
doi:10.1107/S1600536813014177
PMCID: PMC3772454  PMID: 24046597
4.  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
5.  Ethyl 1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-2-phenyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C23H25N3O3, the benzimidazole ring system is essentially planar [maximum deviation = 0.0240 (18) Å]. The mean plane through this ring system forms a dihedral angle of 42.23 (7)° with the benzene ring. The pyrrolidine ring is in an envelope conformation with the flap atom disordered over two sites with occupancies of 0.813 (11) and 0.187 (11). In the crystal, weak C—H⋯O hydrogen bonds form R 2 2(10) ring motifs, which are connected by further C—H⋯O inter­actions, forming ribbons along the b axis. The crystal structure is further stabilized by weak π–π inter­actions involving the imidazole and benzene rings of the benzimidazole ring system [centroid–centroid distances = 3.6788 (11) and 3.6316 (10) Å] and weak C—H⋯π inter­actions.
doi:10.1107/S1600536811054833
PMCID: PMC3274946  PMID: 22346899
6.  Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benz­imidazole-5-carboxyl­ate 
In the title compound, C24H25N3O5, the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methyl­ene C atoms forming the flap. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal packing is further stabillized by weak π–π inter­actions between the benzene rings within the benzimidazole ring system [centroid–centroid distance = 3.7955 (7) Å]. A weak C—H⋯π inter­action involving the benzodioxole ring is also present.
doi:10.1107/S1600536812001420
PMCID: PMC3275223  PMID: 22347079
7.  3-{5-Eth­oxy­carbonyl-1-[3-(2-oxopyrrol­idin-1-yl)prop­yl]-1H-benzimidazol-2-yl}benzoic acid 
In the title compound, C24H25N3O5, the eth­oxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methyl­ene C atom as the flap. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R 2 2(16) loops. C—H⋯O inter­actions link the dimers into a three-dimensional network.
doi:10.1107/S1600536813001116
PMCID: PMC3569823  PMID: 23424569
8.  (2E)-3-(4-Methyl­phen­yl)-1-(3-nitro­phen­yl)prop-2-en-1-one 
The title compound, C16H13NO3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The dihedral angle between the mean planes of the 4-methyl­phenyl and 3-nitro­phenyl groups is 4.0 (3)° in mol­ecule A and 16.2 (7)° in mol­ecule B. Inter­molecular C—H⋯O hydrogen bonding involving the O atoms of the 3-nitro­phenyl group of both independent mol­ecules link the mol­ecules into layers approximately parallel to the (110) plane. The layers are held together by π–π stacking inter­actions between the 4-methyl­phenyl ring of mol­ecule A and the 3-nitro­phenyl ring of mol­ecule B of the adjacent layer, with the distance between the centroids of inter­acting rings being 3.6987 (7) Å.
doi:10.1107/S160053680706182X
PMCID: PMC2914892  PMID: 21200665
9.  (E)-3-(2-Chloro­phen­yl)-1-(4-nitro­phen­yl)prop-2-en-1-one 
In the title compound, C15H10ClNO3, a substituted chalcone, the 2-chloro­phenyl and 4-nitro­phenyl rings make a dihedral angle of 26.48 (6)°. The nitro group makes a dihedral angle of 11.64 (7)° with the plane of the benzene ring to which it is bound. Weak intra­molecular C—H⋯O and C—H⋯Cl inter­actions involving the enone groups generate S(5) ring motifs, which help to stabilize the planarity of the 3-(2-chloro­phen­yl)prop-2-en-1-one segment of the mol­ecule. In the crystal structure, adjacent mol­ecules are stacked in a head-to-tail fashion into columns along the a axis by π–π inter­actions [centroid–centroid distance = 3.6955 (8) Å]. Neighbouring columns are linked by weak C—H⋯O inter­actions.
doi:10.1107/S160053680801218X
PMCID: PMC2961413  PMID: 21202689
10.  (4Z)-4-[(2E)-1-Hy­droxy-3-(3-nitro­phen­yl)prop-2-en-1-yl­idene]-3-methyl-1-(4-methyl­phen­yl)-1H-pyrazol-5(4H)-one 
In the title compound, C20H17N3O4, the dihedral angles between the heterocyclic ring and the toluene and nitro­benzene rings are 4.21 (15) and 11.43 (14)°, respectively. The whole mol­ecule is close to planar (r.m.s. deviation for the 27 non-H atoms = 0.171 Å). Two S(6) rings are formed due to intra­molecular C—H⋯O and O—H⋯O hydrogen bonds. In the crystal, inversion dimers linked by pairs of C—H⋯O bonds generate R 2 2(10) loops and further C—H⋯O bonds link the dimers along the b-axis direction. There exist π–π inter­actions between the heterocyclic rings at a centroid–centroid distance of 3.7126 (10) Å and between the centroids of the benzene rings at a distance of 3.8710 (16) Å.
doi:10.1107/S1600536812025238
PMCID: PMC3393312  PMID: 22807869
11.  (1Z)-1-[(2E)-3-(4-Bromo­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-yl­idene]-2-(2,4-dinitro­phen­yl)hydrazine 
In the title mol­ecule, C21H14BrFN4O4, the mean planes of the two nitro groups form dihedral angles of 3.1 (2) and 7.1 (5)° with the benzene ring to which they are attached. The dinitro-substituted ring forms dihedral angles of 8.6 (2) and 71.9 (2)° with the bromo- and fluoro-substituted benzene rings, respectively. The dihedral angle between the bromo- and fluoro-substituted benzene rings is 80.6 (2)°. There is an intra­molecular N—H⋯O hydrogen bond. In the crystal, pairs of weak C—H⋯O hydrogen bonds form inversion dimers. In addition, π–π stacking inter­actions between the bromo- and dinitro-substituted rings [centroid–centroid separation = 3.768 (2) Å] are observed.
doi:10.1107/S1600536812027328
PMCID: PMC3393993  PMID: 22798858
12.  4-[(E)-2,6-Dichloro­benzyl­ideneamino]-3-{1-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione 
In the title Schiff base compound, C21H22Cl2N4S, the triazole ring makes dihedral angles of 2.15 (11) and 87.48 (11)° with the 2,6-dichloro­phenyl and methyl­propyl­phenyl rings, respectively. Weak intra­molecular C—H⋯S and C—H⋯Cl inter­actions generate S(6) and S(5) ring motifs, respectively. In the crystal structure, centrosymmetrically related mol­ecules are linked into dimers by N—H⋯S hydrogen bonds. These dimers are arranged into sheets parallel to the ab plane and are stacked along the c axis. C—H⋯π inter­actions involving the methyl­propyl­phenyl ring and π–π inter­actions involving the dichloro­phenyl ring [centroid–centroid distance = 3.5865 (3) Å] are also observed.
doi:10.1107/S1600536808021272
PMCID: PMC2962131  PMID: 21203213
13.  (2E)-1-(2,4-Dichloro­phen­yl)-3-[3-(4-nitro­phen­yl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one 
In the title compound, C24H15Cl2N3O3, the C=C double bond is E configured. The 1-phenyl-1H-pyrazole moiety is roughly planar (r.m.s. deviation of all fitted non-H atoms = 0.0780 Å), but the mean planes of the two components are inclined at an angle of 9.95 (7)°. The mean plane defined by the non-H atoms of the 1H-pyrazole ring encloses angles of 9.95 (7), 24.54 (6) and 43.02 (6)° with the mean planes of the different benzene rings. In the crystal, C—H⋯O contacts are present and result in the formation of a double-layer two-dimensional network lying parallel to (110). The shortest inter­centroid distance between two aromatic systems is 3.5455 (7) Å and is apparent between two pyrazole systems. Further π–π inter­actions are manifest between a pair of 4-nitro­phenyl rings [centroid-to-centroid distance = 3.6443 (7) Å] and a pair of 2,4-dichloro­phenyl rings [centroid-to-centroid distance = 3.7797 (7) Å].
doi:10.1107/S1600536812003960
PMCID: PMC3295416  PMID: 22412527
14.  (2E)-1-(3-Bromo­phen­yl)-3-(4,5-dimeth­oxy-2-nitro­phen­yl)prop-2-en-1-one 
In the title compound, C17H14BrNO5, the dihedral angle between the 3-bromo-substituted benzene ring and the 4,5-dimeth­oxy-2-nitro-phenyl ring is 15.2 (1)°. The dihedral angles between the mean plane of the propenone group and the mean planes of the 3-bromo-substituted benzene and 4,5-dimeth­oxy-2-nitro­phenyl rings are 6.9 (6) and 20.5 (5)°, respectively. Weak inter­molecular C—H⋯O inter­actions contribute to crystal stability and π–π inter­actions [centroid–centroid distances = 3.7072 (18) and 3.6326 (18) Å] are also observed.
doi:10.1107/S1600536810041292
PMCID: PMC3009291  PMID: 21589107
15.  2-(4-Methyl­phen­yl)-7-(2-methyl­prop­oxy)-4H-chromen-4-one–6-chloro-2-(4-methyl­phen­yl)-7-(2-methyl­prop­oxy)-4H-chromen-4-one (19/1) 
The title co-crystal, 0.95C20H20O3·0.05C20H19ClO3, arises as the chloride carried over during the synthesis shares a position with an aromatic H atom; the partial occupancies are 0.947 (2) and 0.053 (2) for H and Cl, respectively. The mol­ecular structure is stabilized by intra­molecular C—H⋯O contacts, forming pseudo five- and six-membered rings with S(5) and S(6) graph-set motifs, respectively. The crystal structure features π–π stacking inter­actions between the centroids of the central fused ring systems [centroid–centroid distance = 3.501 (2) Å].
doi:10.1107/S1600536812033430
PMCID: PMC3415021  PMID: 22905008
16.  Methyl 3-[(1H-benzimidazol-1-yl)meth­yl]-1-methyl-4-(4-methyl­phen­yl)-2′-oxopyrrolidine-2-spiro-3′-1-benzimidazole-3-carboxyl­ate 
In the title compound, C29H28N4O3, the pyrrolidine ring adopts a twist conformation whereas the oxindole and benzimidazole residues are approximately planar with maximum deviations of 0.159 (1) and 0.011 (1) Å, respectively. The oxindole residue is almost perpendicular to the benzimidazole residue, making a dihedral angle of 89.2 (1)°. The methyl-substituted benzene ring is oriented at angles of 47.7 (1) and 71.0 (1)°, respectively, with respect to the oxindole and benzimidazole residues. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal, mol­ecules associate via N—H⋯N hydrogen bonds, forming R 2 2(9) dimers.
doi:10.1107/S1600536810035312
PMCID: PMC2983424  PMID: 21587504
17.  (Z)-3-(9-Anthr­yl)-1-(4-bromo­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one 
In the title mol­ecule, C26H16BrN3O3, the anthracene and benzene mean planes make dihedral angles of 63.79 (2) and 14.67 (2)°, respectively, with the plane of the imidazole ring. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules to form centrosymmetric dimers. Weak π–π stacking inter­actions, with centroid–centroid distances of 3.779 (2) and 3.826 (2) Å, supply additional stabilization. The crystal packing also exhibits short inter­molecular contacts between the nitro groups and Br atoms [Br⋯O = 3.114 (2) Å].
doi:10.1107/S1600536809018352
PMCID: PMC2969633  PMID: 21583241
18.  3-[(E)-3-(2,4-Dichloro­phen­yl)prop-2-en­oyl]-4-hy­droxy-2H-chromen-2-one 
In the title compound, C18H10Cl2O4, the chromen-2-one ring system is almost planar [maximum deviation = 0.028 (1) Å] and is inclined at an angle of 16.35 (4)° with respect to the benzene ring. The C=C bond has an E configuration. The mol­ecular conformation is stabilized by an almost symmetric intra­molecular O⋯H⋯O hydrogen bond and a C—H⋯O inter­action, both of which form S(6) ring motifs. In the crystal structure, mol­ecules are linked into sheets lying parallel to (100) via inter­molecular C—H⋯O hydrogen bonds. The crystal packing is further consolidated by π–π stacking inter­actions [centroid-to-centroid separation = 3.6615 (6) Å].
doi:10.1107/S1600536810043837
PMCID: PMC3009251  PMID: 21589179
19.  (2E)-3-(3-Nitro­phen­yl)-1-[4-(piperidin-1-yl)phen­yl]prop-2-en-1-one 
In the title compound, C20H20N2O3, the piperidine ring adopts a chair conformation and its mean plane forms dihedral angles of 19.63 (9) and 19.44 (9)°, respectively, with the benzene and the nitro-substituted benzene ring. The benzene and nitro-substituted benzene rings are almost coplanar and make a dihedral angle of 4.78 (8)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into two-dimensional networks parallel to the ab plane. The crystal packing is further stabilized by π–π inter­actions [maximum centroid–centroid distance = 3.7807 (12) Å].
doi:10.1107/S1600536812008847
PMCID: PMC3343948  PMID: 22590029
20.  Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C23H22N4O4, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methyl­ene C atom at the flap. In the crystal, C—H⋯O and C—H⋯N inter­actions link the mol­ecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π–π stacking inter­actions [centroid–centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536811054572
PMCID: PMC3254578  PMID: 22259529
21.  1-[4-(Prop-2-en-1-yl­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­oxy)phen­yl]-1H-benzimidazole 
In the title compound, C26H24N2O2, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, mol­ecules are linked via C—H⋯π and weak π–π inter­actions [centroid–centroid distance = 3.8070 (7) Å and inter­planar distance = 3.6160 (5) Å].
doi:10.1107/S160053681204559X
PMCID: PMC3588921  PMID: 23476157
22.  (E)-3-(4-Methyl­phen­yl)-1-(4-nitro­phenyl)prop-2-en-1-one 
The asymmetric unit of the title compound, C16H13NO3, contains two independent mol­ecules related approximately by a pseudo-twofold rotation axis. The dihedral angle between the nitro­benzene and methyl­phenyl rings is 42.18 (6)° in one mol­ecule and 12.97 (6)° in the other. In both mol­ecules, the nitro group is slightly twisted away from the attached benzene ring. In the crystal structure, the mol­ecules are stacked along the b axis and are linked via C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536808012257
PMCID: PMC2961424  PMID: 21202687
23.  (2E)-3-(3,4-Dimeth­oxy­phen­yl)-1-(2,5-dimethyl­thio­phen-3-yl)prop-2-en-1-one 
The mol­ecule of the title compound, C17H18O3S, is essentially planar: the phenyl and thio­phene rings form a dihedral angle of 2.79 (10)° and they are inclined to the central propenone unit by 6.20 (15) and 4.78 (15)°, respectively. In the crystal, mol­ecules are connected into dimers via pairs of C—H⋯O inter­actions, generating R 2 2(14) motifs. π–π stacking inter­actions between the thio­phene rings also occur, with a centroid–centroid distance of 3.8062 (12) Å.
doi:10.1107/S1600536810029272
PMCID: PMC3007254  PMID: 21588422
24.  N-(2-Nitro­phen­yl)benzamide 
In the title compound, C13H10N2O3, the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitro­benzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intra­molecular N—H⋯O inter­action to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C—H⋯O contacts generate two centrosymmetric ring systems with R 2 2(14) and R 2 2(20) graph-set motifs, forming zigzag chains down the a axis. π–π inter­actions between adjacent phenyl and nitro­benzene rings [centroid–centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C—H⋯O hydrogen bond generate an extensive three-dimensional network structure.
doi:10.1107/S1600536809024271
PMCID: PMC2977104  PMID: 21583545
25.  2-[1-(4-Bromo­phen­yl)-3-hy­droxy-3-(4-meth­oxy­phen­yl)prop­yl]cyclo­hexa­nol 
In the title compound, C22H27BrO3, the cyclo­hexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 41.9 (4)°. In the crystal, mol­ecules are linked by O—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network. In addition, π–π stacking inter­actions [centroid–centroid distance = 3.953 (6) Å] between the benzene rings of the meth­oxy­benzene groups occur.
doi:10.1107/S1600536813015869
PMCID: PMC3770369  PMID: 24046654

Results 1-25 (429553)