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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.  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
7.  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
8.  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
9.  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
10.  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
11.  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
12.  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
13.  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
14.  4-Methyl­benzoic acid–N′-[(E)-4-methyl­benzyl­idene]pyridine-4-carbohydrazide–water (1/1/1) 
In the title hydrated 1:1 adduct, C8H8O2·C14H13N3O·H2O, the Schiff base mol­ecule exists in an E conformation with respect to the N=C bond [1.2843 (13) Å] and the dihedral angle between the pyridine ring and the benzene ring is 1.04 (5)°. In the crystal, mol­ecules are linked by N—H⋯O, C—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds into sheets lying parallel to the ab plane. The crystal structure also features π–π inter­actions with centroid–centroid distances of 3.6224 (6) and 3.7121 (6) Å.
doi:10.1107/S1600536812016868
PMCID: PMC3344602  PMID: 22590364
15.  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
16.  2-[4-(Methyl­sulfan­yl)phen­yl]naphtho[1,8-de][1,3,2]diaza­borinane 
The title compound, C17H15BN2S, is one member in a series of diaza­borinanes featuring substitution at the 1-, 2- and 3-positions in the nitro­gen–boron heterocycle. The dihedral angle between the mean planes of the naphthalene and phenyl ring systems is 19.86 (6)°. In the crystal structure, two C—H⋯π inter­actions link the mol­ecules into sheets which lie parallel to the bc plane. There is a π–π inter­action between each pair of centrosymmetrically related sheets [centroid–centroid distance = 3.5922 (8) Å].
doi:10.1107/S1600536811014693
PMCID: PMC3120534  PMID: 21754734
17.  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
18.  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
19.  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
20.  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
21.  2-Phenyl-1-(phenyl­sulfin­yl)naphtho[2,1-b]furan 
In the title compound, C24H16O2S, the O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [82.34 (5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21 (6)°. The crystal structure shows π–π inter­actions between the central benzene rings of adjacent mol­ecules [centroid–centroid distance = 3.516 (3) Å], as well as non-classical C—H⋯O hydrogen bonds.
doi:10.1107/S1600536809019977
PMCID: PMC2969545  PMID: 21583281
22.  (2E)-2-[(3-Methyl-5-phen­oxy-1-phenyl-1H-pyrazol-4-yl)methyl­idene]hydrazinecarbothio­amide 
In the title compound, C18H17N5OS, the mean plane of the pyrazole ring [maximum deviation = 0.0031 (12) Å] forms dihedral angles of 19.6 (4) and 9.3 (5)° with the two disorder components of the N-bound benzene ring (with equal occupancies for the two orientations) and a dihedral angle of 72.58 (8)° with the C—O-bonded benzene ring. The mol­ecule exists in a trans conformation with respect to the N=C bond [1.2792 (19) Å]. The mol­ecular structure features an intra­molecular C—H⋯O hydrogen bond, forming an S(6) ring. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds result in the formation of zigzag layers lying parallel to (10-1).
doi:10.1107/S1600536812026931
PMCID: PMC3393955  PMID: 22798820
23.  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
24.  7-Bromo-2-(4-methyl­phen­yl)-1-(methyl­sulfin­yl)naphtho­[2,1-b]furan 
In the title compound, C20H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.030 (2) Å] of the naphtho­furan ring system and the 4-methyl­phenyl ring is 38.49 (9)°. In the crystal, mol­ecules are linked by C—H⋯π and C—Br⋯π [3.871 (2) Å] inter­actions into stacks along the b-axis direction. These stacks are further linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536813016978
PMCID: PMC3770411  PMID: 24046696
25.  2-(4-Bromo­phen­yl)-1-(phenyl­sulfin­yl)naphtho[2,1-b]furan 
In the title compound, C24H15BrO2S, the sulfinyl O atom and the phenyl group of the phenyl­sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The phenyl ring is nearly perpendicular to the plane of the tricyclic naphthofuran system [81.77 (6)°] and is tilted slightly towards it. The 4-bromo­phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 31.12 (4)°. In the crystal structure, non-classical inter­molecular C—H⋯O and C—H⋯Br hydrogen bonds are observed. The crystal structure also exhibits aromatic π–π inter­actions between the furan ring and the central benzene ring of the adjacent naphthofuran system [centroid–centroid distance = 3.768 (3) Å]. In addition, inter­molecular C—Br⋯π inter­actions [3.866 (2) Å] between the Br atom and the phenyl ring of the phenyl­sulfinyl substituent are present.
doi:10.1107/S1600536809029250
PMCID: PMC2977400  PMID: 21583685

Results 1-25 (85639)