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1.  (2E)-2-{[3-Methyl-5-(2-naphth­yloxy)-1-phenyl-1H-pyrazol-4-yl]methyl­idene}hydrazinecarbothio­amide monohydrate 
In the title compound, C22H19N5OS·H2O, the naphthalene ring system and the benzene ring [dihedral angle = 85.19 (8)°] make dihedral angles of 87.02 (9) and 14.41 (10)°, respectively, with the pyrazole ring. The mean plane through the 2-methyl­enehydrazinecarbothio­amide group [C—N—N—C(=S)—N; maximum deviation = 0.022 (1) Å] is slightly twisted from the pyrazole ring [dihedral angle = 5.60 (11)°]. In the crystal, mol­ecules are linked by N—H⋯S, N—H⋯O, O—H⋯S, O—H⋯N and C—H⋯S hydrogen bonds into sheets parallel to the ab plane. π–π inter­actions are also observed [centroid-to-centroid distances = 3.7778 (12) and 3.7010 (12) Å].
doi:10.1107/S1600536812039815
PMCID: PMC3470403  PMID: 23125816
2.  1-(4-Bromo­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H13BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphtho­furan ring. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits slipped π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphtho­furan benzene ring and the furan ring of neighbouring mol­ecules [centroid–centroid distance = 3.655 (2), slippage = 1.136 (2) Å].
doi:10.1107/S160053681202939X
PMCID: PMC3414189  PMID: 22904796
3.  2-Methyl-1-(4-methyl­phenyl­sulfinyl)naphtho­[2,1-b]furan 
In the title compound, C20H16O2S, the 4-methyl­phenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, and by a slipped π–π inter­action between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid-to-centroid distance = 3.671 (2) Å, inter­planar distance = 3.349 (2) Å and slippage = 1.503 (2)°].
doi:10.1107/S1600536812003121
PMCID: PMC3275285  PMID: 22347141
4.  1-(4-Bromo­phenyl­sulfin­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H13BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphtho­furan fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.483 (2) Å, inter­planar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].
doi:10.1107/S1600536812012603
PMCID: PMC3344175  PMID: 22606178
5.  7-Bromo-1-(3-fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H12BrFO3S, the 3-fluoro­phenyl ring makes a dihedral angle of 80.85 (5)° with the mean plane [r.m.s. deviation = 0.009 (2)Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by slipped π–π inter­actions between the furan and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.756 (3) Å and slippage of 1.189 (3) Å].
doi:10.1107/S1600536812040470
PMCID: PMC3470396  PMID: 23125809
6.  7-Bromo-2-phenyl-1-(phenyl­sulfin­yl)naphtho[2,1-b]furan benzene hemisolvate 
The title compound, C24H15BrO2S·0.5C6H6, crystallizes as a benzene hemisolvate. The O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment, and the phenyl ring is almost perpendicular to the plane of the naphthofuran fragment [83.78 (8)°] and is tilted slightly towards it. The 2-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 25.2 (1)°. The crystal structure is stabilized by aromatic π–π inter­actions between the central benzene ring and the furan ring of the neighbouring naphthofuran systems [centroid–centroid distance = 3.611 (3) Å], and by inter­molecular C—H⋯π inter­actions between the benzene H atom of the phenyl­sulfinyl substituent and the 2-phenyl ring of an adjacent mol­ecule. In addition, the crystal structure exhibits a weak non-classical inter­molecular C—H⋯O hydrogen bond.
doi:10.1107/S1600536809025860
PMCID: PMC2977353  PMID: 21583515
7.  3-(4-Chloro­phenyl­sulfon­yl)-2-methyl­naphtho[1,2-b]furan 
The title compound, C19H13ClO3S, was prepared by the oxidation of 3-(4-chloro­phenyl­sulfan­yl)-2-methyl­naphtho[1,2-b]furan with 3-chloro­peroxy­benzoic acid. The 4-chloro­phenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.635 (3) Å], and by C—H⋯π inter­actions between a methyl H atom and the furan ring of an adjacent mol­ecule. In addition, the crystal structure exhibits inter­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808009215
PMCID: PMC2961290  PMID: 21202325
8.  N′-{(E)-[5-(Hy­droxy­meth­yl)furan-2-yl]methyl­idene}pyridine-4-carbohydrazide dihydrate 
In the title compound, C12H11N3O3·2H2O, the dihedral angle formed by the planes of the pyridine and the furan rings of the organic carbohydrazide mol­ecule is 4.66 (7)°. In the crystal, these mol­ecules form stacks along the b-axis direction, neighbouring mol­ecules within each stack being related by inversion and the shortest distance between the centroids of the pyridine and furan rings being 3.714 (1) Å. Mol­ecules from neighboring stacks are linked by pairs of N—H⋯O hydrogen bonds. The water mol­ecules fill the channels between the stacks being linked by O—H⋯O hydrogen bonds into helices along [010]. Besides this, water mol­ecules are involved in O—H⋯N and O—H⋯O hydrogen bonds with the carbohydrazide mol­ecules, thus forming a three-dimensional network, augmented by weak C—H⋯O interactions.
doi:10.1107/S1600536813020114
PMCID: PMC3793823  PMID: 24109410
9.  N′-[(E)-(3-Fluoro­pyridin-2-yl)methyl­idene]pyridine-3-carbohydrazide dihydrate 
The organic molecule in the title dihydrate, C12H9FN4O·2H2O, exists in the E conformation with respect to the azo­methane C=N double bond. The mol­ecule is approximately planar, with a maximum deviation of 0.117 (1) Å for the carbonyl O atom from the mean plane of the mol­ecule. Both pyridine rings are essentially coplanar with the central C(=O)N2C unit [dihedral angles = 1.99 (7) and 5.71 (8)°], exhibiting a significant difference in dihedral angles from its benzohydrazide analogue. The crystal packing features N—H⋯O, O—H⋯N and O—H⋯O hydrogen-bond inter­actions, which lead to the formation of a chain along the c-axis direction through one of the water mol­ecules present, and these chains are stacked one over the other by means of π–π inter­actions [with centroid–centroid distances of 3.7099 (10) and 3.6322 (10) Å] between the aromatic rings in neighbouring anti­parallel mol­ecules, building a three-dimensional supra­molecular network.
doi:10.1107/S1600536814006072
PMCID: PMC3998601  PMID: 24826177
10.  6-(4-Meth­oxy­phen­yl)naphtho[2,3-b][1]benzothio­phene 
The asymmetric unit of the title compound, C23H16OS, contains two independent mol­ecules with opposite orientations of the meth­oxy groups bonded to the benzene rings. The napthobenzothiophene group in the two molecules is separated by an average distance of 3.912 Å. In both mol­ecules, the napthobenzothio­phene unit is almost planar, with r.m.s deviations of 0.0522 and 0.0143 Å. The meth­oxy­phenyl ring makes dihedral angles of 67.0 (6)° and 70.4 (6)° with respect to the napthobenzothio­phene ring system in the two mol­ecules. The crystal packing features C—H⋯S, π–π [centroid–centroid distances = 3.666 (10) and 3.658 (10) Å] and C–H⋯π inter­actions, forming a sheet running along the b-axis direction.
doi:10.1107/S1600536812047137
PMCID: PMC3588996  PMID: 23476232
11.  7-Bromo-2-methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan 
The title compound, C19H13BrO3S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenyl­sulfan­yl)naph­tho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The phenyl ring makes a dihedral angle of 80.4 (2)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π–π stacking inter­actions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring mol­ecules; the centroid–centroid distances within the stack are 3.889 (3) and 3.981 (3) Å. In addition, the stacked mol­ecules exhibit C—H⋯π, inter- and intra­molecular C—H⋯O inter­actions.
doi:10.1107/S160053680801177X
PMCID: PMC2961282  PMID: 21202425
12.  2-Methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan 
The title compound, C19H14O3S, was prepared by the oxidation of 2-methyl-1-(phenyl­sulfan­yl)naphtho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The phenyl ring makes a dihedral angle of 87.13 (4)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.850 (2) Å] and weak C—H⋯π inter­actions. In addition, there are also intra­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808007046
PMCID: PMC2961025  PMID: 21202117
13.  3-(4-Fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[1,2-b]furan 
In the title compound, C19H13FO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 68.59 (5)° with the mean plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O, C—H⋯F and C—H⋯π inter­actions. The crystal structure also exhibits aromatic π–π inter­actions between the central benzene and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.650 (3) Å].
doi:10.1107/S1600536810048361
PMCID: PMC3011502  PMID: 21589581
14.  7-Bromo-1-(4-fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H12BrFO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 80.32 (5)° with the mean plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits aromatic π–π inter­actions between the central benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.564 (3) Å].
doi:10.1107/S160053681005436X
PMCID: PMC3051741  PMID: 21522972
15.  Crystal structure of (E)-2-[(2-hy­droxy-4-meth­oxy­phen­yl)(phen­yl)methyl­idene]-N-phenyl­hydrazine-1-carboxamide 
The title compound, has an E conformation about the azomethine double bond and an intra­molecular O—H⋯N hydrogen bond involving the phenolic hydrogen and the azomethine N atom. In the crystal, mol­ecules are linked by bifurcated N—H⋯O hydrogen bonds involving the same acceptor atom, forming chains propagating along [001].
The title compound, C21H19N3O3, has an E conformation about the azomethine double bond. The central moiety of the hydrazinecarboxamide moiety [–N—N—C(=O)—N–] has an almost coplanar arrangement [maximum deviation for the C atom = 0.010 (2) Å]. This central moiety is flanked by three aromatic rings and its mean plane makes dihedral angles of 24.7 (1), 72.91 (12) and 34.26 (11) Å, respectively, with the phenolic ring, the phenyl ring attached to the same C atom as the phenolic ring, and the phenyl­hydrazine ring. The adjacent phenolic and phenyl rings are twisted away from each other to reduce steric hindrance and make a dihedral angle of 80.59 (12)°. The phenolic and phenyl­hydrazine rings are inclined to one another by 28.89 (11)°. The rigidity of the mol­ecule is increased by an intra­molecular O—H⋯N hydrogen bond involving the phenolic hydrogen and the azomethine N atom. In the crystal, the carbonyl O atom forms bifurcated hydrogen bonds with the two NH atoms of the hydrazinic group, leading to the formation of chains propagating along [001]. Within the chains there are also C—H⋯O hydrogen bonds present. The chains are linked via C=O⋯π [3.4316 (18) Å] and parallel slipped π–π inter­actions, involving inversion-related benzene rings [centroid–centroid distance = 3.8850 (14) Å; inter-planar distance = 3.3895 (10) Å; slippage = 1.899 Å], forming sheets lying parallel to (100).
doi:10.1107/S2056989015005757
PMCID: PMC4438824  PMID: 26029407
crystal structure; hydrazinecarboxamide; supra­molecular; hydrogen bonding; C=O⋯π inter­actions; π–π inter­actions
16.  7-Bromo-2-methyl-1-tosyl­naphtho[2,1-b]furan 
The title compound, C20H15BrO3S, was prepared by the oxidation of 7-bromo-2-methyl-1-(4-tolyl­sulfan­yl)naph­tho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The 4-tolyl ring makes a dihedral angle of 70.96 (6)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π–π stacking inter­actions, with centroid–centroid distances of 3.672 (3) and 3.858 (3) Å between the central benzene and furan rings, and between the brominated benzene and central benzene rings of the naphthofuran system of neighbouring mol­ecules, respectively. In addition, the stacked mol­ecules exhibit C—H⋯π and inter- and intra­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808015286
PMCID: PMC2961428  PMID: 21202666
17.  (E)-4-Meth­oxy-N′-[(6-methyl-4-oxo-4H-chromen-3-yl)methyl­idene]benzo­hydrazide monohydrate 
In the title hydrate, C19H16N2O4·H2O, the 4H-chromen-4-one segment is slightly twisted, with a dihedral angle between the two six-membered rings of 3.30 (5)°. The dihedral angles between the plane of the pyran­one ring and the hydrazide plane and between the planes of the pyran­one ring and the benzene ring of the p-meth­oxy­benzene unit are 26.69 (4) and 2.23 (3)°, respectively. The mol­ecule is connected to the solvent water mol­ecule by an N—H⋯O hydrogen bond. In the crystal, there are π–π stacking inter­actions between centrosymmetrically related pyran­one rings [centroid–centroid distance = 3.5394 (9) Å], as well as bridges formed by the water mol­ecules via O—H⋯O hydrogen bonds.
doi:10.1107/S1600536814013713
PMCID: PMC4120634  PMID: 25161570
18.  2-Phenyl­naphtho­[1,8-de][1,3,2]diaza­borinane 
The title compound, C16H13BN2, is one compound in a series of diaza­borinanes featuring substitution at the 1, 2 and 3 positions in the nitro­gen–boron heterocycle. The title compound is slightly distorted from planarity, with a dihedral angle of 9.0 (5)° between the mean planes of the naphthalene system and the benzene ring. The m-carbon atom of the benzene ring exhibits the greatest deviation of 0.164 (2) Å from the 19-atom mean plane defined by all non-H atoms. The two N—B—C—C torsion angles are 6.0 (3) and 5.6 (3)°. In the crystal, mol­ecules are linked by π–π inter­actions into columns, with a distance of 3.92 (3) Å between the naphthalene ring centroids. Adjacent π-stacked columns, co-linear with the b-axis, are linked by C—H⋯π inter­actions.
doi:10.1107/S1600536811026985
PMCID: PMC3213450  PMID: 22091029
19.  (N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chloro­phen­yl)ethane-1,2-diyl­idene]bis­(3-methyl-1-benzofuran-2-carbohydrazide) 
In the title compound, C28H21ClN4O4, the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C—N—N=C and C—N—N=C—C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intra­molecular N—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯(O,N) and C—H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C—H⋯O hydrogen bond into a sheet parallel to the bc plane. π–π inter­actions [centroid-to-centroid distances = 3.4845 (12)–3.6250 (13) Å] are also observed.
doi:10.1107/S1600536812030504
PMCID: PMC3414328  PMID: 22904861
20.  (1Z,2E)-N′-{1-[2-(4-Bromo­phen­yl)hydrazin-1-yl­idene]-1-chloro­propan-2-yl­idene}thio­phene-2-carbohydrazide 
In the title compound, C14H12BrClN4OS, the thienyl ring is disordered over two orientations with a site-occupancy ratio of 0.853 (2):0.147 (2). The mol­ecule is roughly planar, with the dihedral angles between the thienyl and benzene rings being 6.24 (16) and 9.7 (11)° for the major and minor components, respectively. The central fragment is almost planar [r.m.s. deviation = 0.0275 (2) Å for the ten non-H atoms]. The mean plane through this middle unit makes a dihedral angle of 2.71 (7)° with the benzene ring, whereas these values are 4.46 (15) and 7.7 (11)° for the major and minor components of the thienyl ring, respectively. In the crystal, mol­ecules are linked into dimers by pairs of N—H⋯O hydrogen bonds, forming R 2 2(8) ring motifs. These dimers are arranged into sheets parallel to the ac plane.
doi:10.1107/S1600536812017114
PMCID: PMC3344617  PMID: 22590379
21.  2-Methyl-1-(3-methyl­phenyl­sulfon­yl)naphtho­[2,1-b]furan 
In the title compound, C20H16O3S, the dihedral angle between the mean planes of the naphtho­furan and 3-methyl­phenyl fragments is 88.56 (2)°. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked by π–π inter­actions between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.701 (2) Å] into supra­molecular chains running along the a-axis direction.
doi:10.1107/S1600536814005157
PMCID: PMC3998563  PMID: 24826129
22.  N′-[(1E)-(4-Fluoro­phen­yl)methyl­idene]thio­phene-2-carbohydrazide 
In the title compound, C12H9FN2OS, the thienyl ring is disordered over two positions, with the S atom of the major component [occupancy = 87.08 (16)°] oriented towards the ortho-H atom of the benzene ring. The mol­ecule is nearly planar, the dihedral angle between the thio­phene and benzene rings being 13.0 (2)° in the major component. The azomethine C=N double bond in the mol­ecule is of an E configuration. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536811056121
PMCID: PMC3275004  PMID: 22346949
23.  N′-[(1E)-(2,6-Difluoro­phen­yl)methyl­idene]thio­phene-2-carbohydrazide 
In the title compound, C12H8F2N2OS, the thienyl ring is disordered over two positions, with the S atom of the major component [occupancy = 75.03 (18)%] oriented away from an ortho-F atom of the benzene ring. The mol­ecule is nearly planar, the dihedral angle between the thio­phene and benzene rings being 6.19 (18) (in the major component) or 3.5 (6)° (in the minor component). The azomethine C=N double-bond in the mol­ecule is of an E configuration. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, generating inversion dimers.
doi:10.1107/S160053681105611X
PMCID: PMC3275005  PMID: 22346950
24.  Crystal structure of (4Z)-4-{[(2-chloro­phen­yl)amino](furan-2-yl)methyl­idene}-3-methyl-1-phenyl-4,5-di­hydro-1H-pyrazol-5-one 
In the title compound, C21H16ClN3O2, the pyrazolone ring and the O=C—C=C—N mean plane [maximum deviation = 0.022 (2) Å] are nearly coplanar, making a dihedral angle 4.56 (8)°, while the phenyl and pyrazole rings subtend a dihedral angle of 19.75 (8)°. The compound is in the enamine–keto form and its structure is stabilized by an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked via C—H⋯N hydrogen bonds, forming chains along [010]. Between the chains there are π–π inter­actions [inter-centroid distances = 3.3902 (9) and 3.5956 (11) Å], linking the chains to form sheets parallel to (10-1).
doi:10.1107/S2056989015002698
PMCID: PMC4350689  PMID: 25844235
crystal structure; pyrazolone; 4-acyl­pyrazolone; o-chloro­aniline; hydrogen bonding
25.  7-Bromo-1-(4-chloro­phenyl­sulfan­yl)-2-phenyl­naphtho[2,1-b]furan 
In the title compound, C24H14BrClOS, the S-bound 4-chloro­phenyl ring is nearly perpendicular to the plane of the naphthofuran fragment [dihedral angle = 83.34 (3)°] and the phenyl ring in the 2-position is rotated out of the naphthofuran plane by a dihedral angle of 15.23 (5)°. The crystal structure is stabilized by aromatic π–π inter­actions between the furan and the central benzene rings of the neighbouring naphthofuran fragments, and between the outer benzene rings of the neighbouring naphthofuran fragments; the centroid–centroid distances within the stack are 3.879 (2) and 3.857 (2) Å. In addition, inter­molecular C—Cl⋯π inter­actions [3.505 (2) Å] between the Cl atom and the 2-phenyl ring are present.
doi:10.1107/S1600536809052945
PMCID: PMC2980269  PMID: 21580059

Results 1-25 (121475)