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1.  1-[5-Methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazol-4-yl]ethanone 
The asymmetric unit of the title compound, C11H10N4O3, contains two independent mol­ecules in which the benzene rings make dihedral angles of 38.3 (2) and 87.1 (2)° with respect to the triazole rings. In the crystal, the mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains along [021]. Further, weak C—O⋯π [3.865 (5) Å, 83.8 (3)°] and N—O⋯π [3.275 (5) and 3.240 (6) Å, 141.8 (4) and 102.8 (3)°] inter­actions are observed.
doi:10.1107/S1600536813029425
PMCID: PMC3884370  PMID: 24454146
2.  (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
3.  4-Bromo­acetyl-3-phenyl­sydnone 
In the title compound (systematic name: 4-bromoacetyl-1,2,3-oxadiazol-3-ylium-5-olate), C10H7BrN2O3, the 1,2,3-oxadiazole ring and bromo­acetyl group are essentially planar [maximum deviation = 0.010 (4) and 0.013 (3) Å respectively] and form dihedral angles of 59.31 (19) and 67.96 (11)°, respectively, with the phenyl ring. The 1,2,3-oxadiazole ring is twisted slightly from the mean plane of the bromo­acetyl group, forming a dihedral angle of 9.16 (24)°. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R 2 2(12) ring motifs. The dimers are further connected by weak C—H⋯O hydrogen bonds into an infinite tape parallel to the b axis. In addition, π–π stacking inter­actions [centroid–centroid distance = 3.6569 (19) Å] and short inter­molecular contacts [O⋯O = 2.827 (3) and C⋯C = 3.088 (5) Å] are observed.
doi:10.1107/S1600536812026049
PMCID: PMC3393916  PMID: 22798781
4.  3-(1-Benzofuran-2-yl)-1H-1,2,4-triazole-5(4H)-thione monohydrate 
In the title hydrate, C10H7N3OS·H2O, the essentially planar benzofuran [maximum deviation = 0.006 (1) Å] and 4,5-dihydro-1H-1,2,4-triazole [maximum deviation = 0.007 (1) Å] rings form a dihedral angle of 11.67 (6)°. In the crystal, O—H⋯N, O—H⋯S, N—H⋯O and N—H⋯S hydrogen bonds link the mol­ecules into sheets lying parallel to the bc plane. Aromatic π–π stacking inter­actions [centroid–centroid distances = 3.5078 (8)–3.6113 (8) Å] are also observed.
doi:10.1107/S1600536812025305
PMCID: PMC3393331  PMID: 22807888
5.  N′-(3,4-Dichloro­benzyl­idene)-5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carbohydrazide 
In the title compound, C17H12Cl2N6O3, the 1H-1,2,3-triazole ring [maximum deviation = 0.003 (1) Å] forms dihedral angles of 34.08 (6) and 28.38 (6)°, respectively, with the nitro- and dichloro-substituted benzene rings. The dihedral angle between the benzene rings is 6.68 (5)°. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into chains running parallel to the a axis.
doi:10.1107/S1600536812023112
PMCID: PMC3379459  PMID: 22719657
6.  (E)-4-{[(3-Propyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-4-yl)imino]­meth­yl}-3-(p-tol­yl)-1,2,3-oxadiazol-3-ium-5-olate 
The title compound, C15H16N6O2S, exists in a trans configuration with respect to the acyclic N=C bond. The 1,2,3-oxadiazol-3-ium ring makes dihedral angles of 10.59 (8) and 73.94 (8)°, respectively, with the 1,2,4-triazole and benzene rings. The mol­ecular structure is stabilized by an intra­molecular C—H⋯S hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of inter­molecular N—H⋯S hydrogen bonds, generating eight-membered R 2 2(8) ring motifs. The dimers are further connected by C—H⋯O hydrogen bonds, forming a sheet parallel to the bc plane. The ethyl group is disordered over two sets of sites with occupancies of 0.744 (7) and 0.256 (7).
doi:10.1107/S1600536811037287
PMCID: PMC3201362  PMID: 22065521
7.  4-[2-(4-Chloro­phen­yl)hydrazinyl­idene]-3-methyl-1H-pyrazol-5(4H)-one 
In the title compound, C10H9ClN4O, the pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 7.06 (14)° with the chloro­benzene ring. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(16) ring motifs. The dimers are further connected by N—H⋯N hydrogen bonds, thereby forming layers lying parallel to the bc plane.
doi:10.1107/S1600536811037020
PMCID: PMC3201479  PMID: 22058782
8.  Ethyl 5-methyl-1-(4-nitro­phen­yl)-1H-1,2,3-triazole-4-carboxyl­ate 
In the title compound, C12H12N4O4, the 1,2,3-triazole ring and the nitro group form dihedral angles of 37.93 (5) and 8.97 (12)°, respectively, with the phenyl ring. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked by C—H⋯N hydrogen bonds into layers lying parallel to (100). The crystal structure is further consolidated by π–π [centroid–centroid distance = 3.6059 (6) Å] inter­actions.
doi:10.1107/S1600536811033940
PMCID: PMC3200591  PMID: 22059001
9.  3-(4-Nitro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione 
In the title compound, C8H6N4O2S, the 1,2,4-triazole ring and the nitro group form dihedral angles of 6.26 (13) and 9.5 (3)°, respectively, with the phenyl ring. In the crystal, the mol­ecules are linked via pairs of N—H⋯S hydrogen bonds, generating [010] chains which contain R 2 2 (8) ring motifs. The crystal structure is further stabilized by π–π stacking [centroid–centroid distance = 3.5491 (14) Å] inter­actions.
doi:10.1107/S1600536811033952
PMCID: PMC3200626  PMID: 22065655
10.  2-[5-Methyl-2-(propan-2-yl)phen­oxy]-N′-{2-[5-methyl-2-(propan-2-yl)phen­oxy]acet­yl}acetohydrazide 
The complete mol­ecule of the title compound, C24H32N2O4, is generated by a crystallographic inversion center. The 1,2-diethyl­hydrazine moiety is nearly planar, with a maximum deviation of 0.024 (1) Å, and is inclined at a dihedral angle of 54.20 (4)° with the phenyl ring. In the crystal, [001] chains are formed, with adjacent mol­ecules in the chain linked by pair of inter­molecular N—H⋯O hydrogen bonds, generating R 2 2(10) ring motifs. Inter­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536811033964
PMCID: PMC3200946  PMID: 22059000
11.  4-Acetyl-3-(p-anis­yl)sydnone 
The asymmetric unit of the title compound [systematic name: 4-acetyl-3-(4-meth­oxy­phen­yl)-1,2,3-oxadiazol-3-ium-5-olate], C11H10N2O4, contains four crystallographically independent mol­ecules. The 1,2,3-oxadiazole rings are almost planar [maximum deviations = 0.006 (3), 0.006 (3), 0.002 (3) and 0.009 (3) Å] and form dihedral angles of 55.03 (14), 61.02 (13), 58.36 (14) and 53.79 (15)° with their attached benzene rings. In the crystal, inter­molecular C—H⋯O and C—H⋯N hydrogen bonds link the mol­ecules, forming sheets parallel to (011).
doi:10.1107/S1600536811018484
PMCID: PMC3120361  PMID: 21754857
12.  7-(4-Chloro­benzyl­idene)-3-[(4-chloro­phen­oxy)meth­yl]-6-(4-nitro­thio­phen-2-yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazine 
In the title compound, C22H13Cl2N5O3S2, the thia­diazine ring adopts a half-chair conformation. The benzene rings of the chloro­phen­oxy and chloro­benzyl groups and the thio­phene ring form dihedral angles of 35.6 (1), 80.7 (1) and 14.2 (1)°, respectively, with the triazole ring. In the crystal, mol­ecules are connected into sheets parallel to (11) by inter­molecular C—H⋯N and C—H⋯Cl hydrogen bonds. In addition, π–π stacking inter­actions are observed between thio­phene and triazole rings, and between inversion-related triazole rings [centroid–centroid distances = 3.5975 (11) and 3.4324 (11) Å].
doi:10.1107/S1600536811015637
PMCID: PMC3089255  PMID: 21754553
13.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl­sydnone 
The title compound, C18H13ClN6O2S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.002 (1) Å] and forms dihedral angles of 50.45 (7) and 61.21 (6)° with the aromatic rings. In the crystal, inter­molecular N—H⋯N, C—H⋯Cl and C—H⋯S hydrogen bonds link the mol­ecules into layers parallel to ab plane. The crystal packing is stabilized by C—H⋯π inter­actions and further consolidated by π–π inter­actions involving the phenyl rings [centroid–centroid distance = 3.6306 (7) Å].
doi:10.1107/S1600536811013912
PMCID: PMC3089094  PMID: 21754481
14.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-(4-meth­oxy­phen­yl)sydnone 
The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intra­molecular C—H⋯O hydrogen bond stabilizes the mol­ecular structure and forms an S(6) ring motif. In the crystal packing, inter­molecular N—H⋯N hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R 2 2(8) ring motifs. The dimers are then linked into a three-dimensional network by inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds, and by C—H⋯π inter­actions. Further stabilization is provided by π–π inter­actions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.
doi:10.1107/S1600536811013900
PMCID: PMC3089192  PMID: 21754480
15.  4-(2-{[4-Amino-6-(4-nitro­benz­yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan­yl}acet­yl)-3-phenyl­sydnone 
In the crystal, C20H15N7O6S, the dihedral angle between the oxadiazole and triazine rings is 86.94 (7)°. The oxadiazole ring makes a dihedral angle of 52.96 (8)° with the phenyl ring, while the triazine ring makes a dihedral angle of 82.08 (7)° with the benzene ring. In the structure, mol­ecules are linked by a pair of N—H⋯O hydrogen bonds, forming an inversion dimer. The dimers are further stacked along the a axis via N—H⋯N hydrogen bonds. Weak inter­molecular C—H⋯O inter­actions are also observed.
doi:10.1107/S1600536811014504
PMCID: PMC3089265  PMID: 21754498
16.  3-(p-Tol­yl)-4-{3-[(phenyl­amino)­meth­yl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thia­diazin-6-yl}sydnone 
In the title compound, C20H17N7O2S (systematic name: 3-(4-methyl­phen­yl)-4-{3-[(phenyl­amino)­meth­yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl}-1,2,3-oxadiazol-3-ium-5-olate), the 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 57.99 (6) and 54.48 (6)° with the phenyl and benzene rings, respectively, while the 1,2,4-triazole ring forms corresponding angles of 37.35 (6) and 73.89 (6)°. The dihedral angle between the oxadiazol-3-ium and 1,2,4-triazole rings is 21.12 (6)°. In the crystal, the mol­ecules are linked via inter­molecular N—H⋯O and C—H⋯N hydrogen bonds into a layer parallel to the (100) plane. The crystal structure is further consolidated by C—H⋯π inter­actions. An intra­molecular C—H⋯O hydrogen bond is also observed, which generates an S(6) ring motif.
doi:10.1107/S1600536811010786
PMCID: PMC3099773  PMID: 21754026
17.  4-({[4-Amino-6-(p-bromo­benz­yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan­yl}acet­yl)-3-phenyl­sydnone 
In the title compound, C20H15BrN6O4S [symstematic name: 4-({[4-amino-6-(p-bromo­benz­yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan­yl}acet­yl)-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate], the 4,5-dihydro-1,2,4-triazine ring is essentially planar [maximum deviation = 0.020 (1) Å] and is inclined at dihedral angles of 89.06 (9), 82.21 (8) and 83.98 (8)° with respect to the oxadiazol-3-ium, phenyl and benzene rings. The oxadiazol-3-ium ring forms dihedral angles of 52.71 (9) and 8.77 (9)°, respectively, with the phenyl and benzene rings. In the crystal, the mol­ecules are linked via pairs of inter­molecular N—H⋯O hydrogen bonds, generating R 2 2(10) ring motifs and are further linked via inter­molecular N—H⋯N and weak C—H⋯O hydrogen bonds into infinite columns along [100].
doi:10.1107/S1600536811010798
PMCID: PMC3099816  PMID: 21754025
18.  4-{(Z)-2-[(E)-Benzyl­idenehydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate 
The title compound, C18H14N6O2S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 53.70 (4) and 60.26 (4)° with the two phenyl rings. In the crystal, mol­ecules are linked via pairs of inter­molecular N—H⋯N hydrogen bonds, generating R 2 2(8) ring motifs, and are further linked via inter­molecular C—H⋯O and C—H⋯S hydrogen bonds into a three-dimensional network. The short inter­molecular distance between the oxadiazol-3-ium rings [3.4154 (4) Å] indicates the existence of a π–π inter­action.
doi:10.1107/S1600536811010609
PMCID: PMC3100016  PMID: 21754237
19.  2,3-Dibromo-3-(4-bromo­phen­yl)-1-[3-(4-meth­oxy­phen­yl)sydnon-4-yl]propan-1-one 
In the title compound {systematic name: 4-[2,3-dibromo-3-(4-bromo­phen­yl)propano­yl]-3-(4-meth­oxy­phen­yl)-1,2,3-oxa­dia­zol-3-ylium-5-olate}, C18H13Br3N2O4, the central oxadiazole ring, which is essentially planar with a maximum deviation of 0.016 (3) Å, makes dihedral angles of 29.98 (16) and 52.04 (16)°, respectively, with the terminal bromo-substituted and meth­oxy-substituted benzene rings. An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif.
doi:10.1107/S1600536811010002
PMCID: PMC3099938  PMID: 21754217
20.  4-[2-(2-Benzyl­idene­hydrazin­ylidene)-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl]-3-(4-meth­oxy­phen­yl)­sydnone 
In the title compound, C19H16N6O3S, the 3,6-dihydro-1,3,4-thia­diazine ring adopts a twist-boat conformation. The dihedral angle between the meth­oxy-substituted benzene ring and the oxadiazole ring is 71.91 (7)°. In the crystal structure, centrosymmetrically related mol­ecules are linked into dimers via pairs of inter­molecular N—H⋯N hydrogen bonds, generating R 2 2(8) ring motifs. There is an intra­molecular C—H⋯O hydrogen bond which generates an S(6) ring motif.
doi:10.1107/S1600536811009329
PMCID: PMC3099954  PMID: 21754176
21.  4-({[6-(4-Chloro­benz­yl)-4-methyl-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan­yl}acetyl)-3-phenyl­sydnone 
In the title syndone (1,2,3-oxadiazol-3-ylium-5-olate) compound, C21H16ClN5O4S, the dihedral angle between the benzene and oxadiazole rings is 55.62 (11)° and that between the triazine and the chloro-substituted phenyl rings is 82.45 (9)°. There is an intra­molecular C—H⋯S hydrogen bond, which generates an S(5) ring motif. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(20) loops. The dimers are connected by C—H⋯N and C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811007689
PMCID: PMC3099780  PMID: 21754104
22.  2,3-Dibromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)propan-1-one 
In the title compound [systematic name: 4-(2,3-dibromo-3-phenyl­propano­yl)-3-phenyl-1,2,3-oxadiazol-3-ylium-5-olate], C17H12Br2N2O3, the oxadiazole ring is essentially planar, with a maximum deviation of 0.001 (3) Å. The central oxadiazole ring makes dihedral angles of 73.3 (2) and 29.0 (2)° with the adjacent and remote phenyl rings, respectively. In the crystal, adjacent mol­ecules are connected by C—H⋯O hydrogen bonds, forming a supra­molecular chain along the c axis. There is an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif.
doi:10.1107/S1600536811008026
PMCID: PMC3099808  PMID: 21754100
23.  2,3-Dibromo-3-(5-nitro-2-fur­yl)-1-phenyl­propan-1-one 
In the title compound, C13H9Br2NO4, the phenyl and 2-nitro­furan rings are linked by a 2,3-dibromo­propanal group, six atoms of which, including a furyl C atom, are disordered over two positions with a site-occupancy ratio of 0.733 (11):0.267 (11). The dihedral angle between the furan [maximum deviation = 0.028 (4) Å] and phenyl rings in the major component is 16.9 (3)°. In the minor component, the corresponding values are 0.87 (4) Å and 23.3 (5)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into two-dimensional arrays parallel to the ab plane.
doi:10.1107/S1600536811003552
PMCID: PMC3052152  PMID: 21522313
24.  4-[(3-Benzamido­methyl-6-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-7-yl)carbon­yl]-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate 0.06-hydrate 
The asymmetric unit of the title compound, C27H21N7O4S·0.06H2O, contains four syndone mol­ecules and a water mol­ecule with a site occupancy of 0.25. In two of the syndone mol­ecules, three atoms in a terminal phenyl ring are disordered over two sets of sites, with occupancy ratios of 0.500 (18):0.500 (18) and 0.512 (17):0.488 (17). The dihedral angles between terminal phenyl rings for the syndone mol­ecules are 23.3 (4), 45.57 (16), 68.46 (16) and 56.5 (3)°. In the crystal, mol­ecules are connected via N—H⋯N, N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536810049998
PMCID: PMC3050302  PMID: 21522639
25.  2,3-Dibromo-1-(4-methyl­phen­yl)-3-(5-nitro­furan-2-yl)propan-1-one 
In the title compound, C14H11Br2NO4, the whole mol­ecule is disordered over two positions with a refined occupancy ratio of 0.539 (9):0.461 (9). The 2-nitro­furan and toluene groups are approximately planar, with maximum deviations of 0.176 (11) and 0.121 (14) Å, respectively, in the major component and 0.208 (11) and 0.30 (17) Å in the minor component. The dihedral angles between the 2-nitro­furan and toluene groups are 8.7 (5) and 8.0 (9)° for the major and minor components, respectively. In the crystal, weak inter­molecular C—H⋯O inter­actions connect mol­ecules into a three-dimensional network, generating R 2 1(6) ring motifs.
doi:10.1107/S1600536810050488
PMCID: PMC3050337  PMID: 21522790

Results 1-25 (43)