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1.  3-Ethyl-4-methyl-1H-pyrazol-2-ium-5-olate 
The title compound, C6H10N2O, is a zwitterionic pyrazole derivative. The crystal packing is predominantly governed by a three-center iminium–amine N+—H⋯O−⋯H—N inter­action, leading to an undulating sheet-like structure lying parallel to (100).
doi:10.1107/S160053681102808X
PMCID: PMC3213569  PMID: 22091146
2.  4-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}-N-ethyl­piperazine-1-carboxamide 
The asymmetric unit of the title compound, C23H23ClFN5O2, contains two crystallographically independent mol­ecules. In one mol­ecule, the pyrazole ring makes dihedral angles of 43.93 (7) and 35.82 (7)°, respectively, with the fluoro- and chloro-substituted benzene rings, while the corresponding angles in the other mol­ecule are 52.26 (8) and 36.85 (7)°. The piperazine rings adopt chair conformations. In the crystal, adjacent mol­ecules are connected via inter­molecular N—H⋯O, C—H⋯F, C—H⋯N and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The crystal structure is further stabilized by a weak π–π inter­action with a centroid–centroid distance of 3.6610 (8) Å and by C—H⋯π inter­actions.
doi:10.1107/S1600536811023178
PMCID: PMC3151813  PMID: 21837133
3.  1,3-Dimethyl-4-phenyl­sulfanyl-1H-pyrazol-5-ol 
In the title compound, C11H12N2OS, the pyrazole ring makes a dihedral angle of 85.40 (8)° with the phenyl ring. In the crystal, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link mol­ecules into a two-dimensional network parallel to the bc plane.
doi:10.1107/S1600536811004922
PMCID: PMC3052103  PMID: 21522387
4.  3-Isobutyl-4-phenyl­sulfan­yl-1H-pyrazol-5-ol 
The asymmetric unit of the title compound, C13H16N2OS, contains two independent mol­ecules (A and B). The pyrazole ring [maximum deviations = 0.0049 (17) Å in mol­ecule A and 0.0112 (19) Å in mol­ecule B] makes a dihedral angle of 70.23 (11) and 73.18 (12)° with the phenyl ring in mol­ecules A and B, respectively. The isobutyl group in mol­ecule B is disordered over two sets of sites with a ratio of refined occupancies of 0.858 (5):0.142 (5). In the crystal, mol­ecules A and B are linked via a pair of inter­molecular N—H⋯O hydrogen bonds, generating an R 2 2(8) ring motif. These ring motifs are further linked into two-dimensional arrays parallel to the bc plane by inter­molecular N—H⋯O and weak C—H⋯S hydrogen bonds. The crystal is further stablized by weak π–π inter­actions [centroid–centroid distances = 3.5698 (13) and 3.5287 (12) Å].
doi:10.1107/S1600536811002170
PMCID: PMC3051470  PMID: 21523124
5.  5-Ethyl-2-(4-fluoro­phen­yl)-4-phen­oxy-1H-pyrazol-3(2H)-one 
In the title compound, C17H15FN2O2, the essentially planar pyrazole ring [maximum deviation = 0.026 (1) Å] makes dihedral angles of 72.06 (7) and 33.05 (7)°, with the phenyl and fluoro­benzene rings, respectively. The dihedral angle between the two six-membered rings is 87.88 (7)°. In the crystal, inter­molecular N—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into layers lying parallel to the bc plane.
doi:10.1107/S1600536811000754
PMCID: PMC3051690  PMID: 21523133
6.  5-Ethyl-4-phenyl-1H-pyrazol-3(2H)-one 
The asymmetric unit of the title compound, C11H12N2O, consists of two crystallographically independent mol­ecules (A and B) with similar geometries. Both mol­ecules exist in a keto form, the C=O bond length being 1.286 (2) Å in A and 1.283 (2) Å in B. The dihedral angles between the pyrazole ring and the attached phenyl ring are 43.28 (12) and 46.88 (11)°, respectively, for A and B. The ethyl unit in mol­ecule B is disordered over two positions with a site-occupancy ratio of 0.508 (5):0.492 (5). In the crystal, each of the independent mol­ecules forms a centrosymmetric dimer with an R 2 2(8) ring motif through a pair of N—H⋯O hydrogen bonds. These dimers are further connected into a three-dimensional network by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds. Inter­molecular C—H⋯π inter­actions are also present.
doi:10.1107/S1600536811001589
PMCID: PMC3051742  PMID: 21523076
7.  4-Methyl-5-phenyl-1H-pyrazol-3(2H)-one 
The asymmetric unit of the title compound, C10H10N2O, contains two crystallographically independent mol­ecules with similar geometries, which exist in the keto form. The C=O bond lengths are 1.2878 (12) Å in mol­ecule A and 1.2890 (12) Å in mol­ecule B, indicating that the compound undergoes enol-to-keto tautomerism during the crystallization process. In mol­ecule A, the pyrazole ring is approximately planar [maximum deviation = 0.007 (1) Å] and forms a dihedral angle of 36.67 (6)° with the attached phenyl ring. In mol­ecule B, the dihedral angle formed between the pyrazole ring [maximum deviation = 0.017 (1) Å] and the phenyl ring is 41.19 (6)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link neighbouring mol­ecules into dimers generating R 2 2(8) ring motifs. These dimers are linked into ribbons along [101] via inter­molecular N—H⋯O hydrogen bonds, forming R 4 2(10) ring motifs.
doi:10.1107/S160053681005213X
PMCID: PMC3050219  PMID: 21522659
8.  3-(2,5-Dimethyl­furan-3-yl)-1H-pyrazol-5-ol–ethyl 3-(propan-2-yl­idene)carbazate (1/1). Corrigendum 
Corrigendum to Acta Cryst. (2010), E66, o3020–o3021.
The address of three of the authors in the paper by Shahani et al. [Acta Cryst. (2010), E66, o3020–o3021] is corrected.
doi:10.1107/S1600536810047859
PMCID: PMC3011539  PMID: 21589200
9.  1-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl]}piperidin-4-one 
In the title compound, C21H17ClFN3O2, the 1H-pyrazole ring makes dihedral angles of 36.73 (7), 18.73 (7) and 60.88 (8)°, respectively, with the mean planes of the chloro­phenyl, 4-oxo­piperidine and fluoro­phenyl rings. The mol­ecular structure is stabilized by an intra­molecular C—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains along [101]. In addition, inter­molecular C—H⋯F hydrogen bonds with an R 2 1(7) ring motif connect neighbouring chains into layers parallel to the ac plane.
doi:10.1107/S1600536810047215
PMCID: PMC3011612  PMID: 21589523
10.  5-Isobutyl-4-phenyl­sulfonyl-1H-pyrazol-3(2H)-one 
The title compound, C13H16N2O3S, consists of two crystallographically independent mol­ecules with similar geometries and exists in a keto form, the C=O bond lengths being 1.267 (2) and 1.254 (2) Å. In both mol­ecules, the pyrazole rings are approximately planar, with maximum deviations of 0.017 (2) and 0.010 (2) Å, and the dihedral angles between the pyrazole and phenyl rings are 83.63 (11) and 70.07 (12)°. In one mol­ecule, an intra­molecular C—H⋯O hydrogen bond with an S(6) ring motif is observed. In the crystal, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into two-dimensional networks parallel to the ab plane.
doi:10.1107/S1600536810044181
PMCID: PMC3011737  PMID: 21589363
11.  3-(2,5-Dimethyl­furan-3-yl)-1H-pyrazol-5-ol–ethyl 3-(propan-2-yl­idene)carbazate (1/1) 
In the title 1:1 adduct, C6H12N2O2·C9H10N2O2, the maximum deviations from the 1H-pyrazole-5-ol and furan rings are 0.014 (1) and 0.003 (1) Å, respectively. The dihedral angle formed between the 1H-pyrazol-5-ol and 2,5-dimethyl­furan rings is 21.07 (5)°. In the crystal, pairs of inter­molecular O—H⋯N hydrogen bonds form inversion dimers of the 3-(2,5-dimethyl­furan-3-yl)-1H-pyrazol-5-ol species, generating R 2 2(8) ring motifs. Mol­ecules are further linked by inter­molecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds to form ribbons along the [010] direction containing bifurcated R 1 2(5) and R 2 1(7) ring motifs. Further stablization of the packing is provided by weak π–π [centroid–centroid distance = 3.5686 (15) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536810043886
PMCID: PMC3009126  PMID: 21589178
12.  4,5,6,7,8,9-Hexahydro-2H-cyclo­octa[c]pyrazol-1-ium-3-olate 
The title compound, C9H14N2O, exists in the zwitterionic form in the crystal. The cyclo­octane ring adopts a twisted boat-chair conformation. In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into sheets lying parallel to bc. The structure is also stabilized by π–π inter­actions, with a centroid-to-centroid distance of 3.5684 (8) Å.
doi:10.1107/S1600536810043904
PMCID: PMC3009207  PMID: 21589177
13.  Ethyl 2-[5-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]-4-methyl­thia­zole-5-carboxyl­ate 
In the title compound, C22H17ClFN3O2S, the pyrazole ring is approximately planar with a maximum deviation of 0.001 (4) Å and makes dihedral angles of 4.95 (19), 35.78 (18) and 54.73 (18)° with the thia­zole, fluoro­benzene and chloro­benzene rings, respectively. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the a axis.
doi:10.1107/S1600536810042066
PMCID: PMC3009042  PMID: 21589099
14.  1-(4-Fluoro­phen­yl)-3-methyl-4-phenyl­sulfanyl-1H-pyrazol-5(4H)-one 
The title compound, C16H13FN2OS, has undergone enol-to-keto tautomerism during the crystallization process. The 1H-pyrazole-5-one ring [maximum deviation = 0.0198 (11) Å] is inclined at angles of 33.10 (5) and 79.57 (5)° with respect to the fluoro­phenyl [maximum deviation = 0.0090 (12) Å] and phenyl­thiol [maximum deviation = 0.0229 (3) Å] rings attached to it. In the crystal, neighbouring mol­ecules are linked into inversion dimers, generating R 2 2(8) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the bc plane via inter­molecular N—H⋯O, C—H⋯F and C—H⋯O hydrogen bonds. The crystal is further stabilized by weak π–π [centroid–centroid distance = 3.6921 (7) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536810040596
PMCID: PMC3009262  PMID: 21589006
15.  5-Cyclo­hexyl-4-methyl-1H-pyrazol-3(2H)-one monohydrate 
In the title compound, C10H16N2O·H2O, the cyclo­hexane ring is in a chair conformation and its least-squares plane makes a dihedral angle of 53.68 (5)° with the approximately planar pyrazole ring [maximum deviation = 0.034 (1) Å]. Pairs of inter­molecular N—H⋯O hydrogen bonds form inversion dimers between neighbouring pyrazolone mol­ecules, generating R 2 2(8) ring motifs. The pyrazolone and water mol­ecules are further linked by inter­molecular N—H⋯O, C—H⋯O and O—H⋯O hydrogen bonds into two-dimensional sheets parallel to the bc plane.
doi:10.1107/S1600536810039164
PMCID: PMC3009194  PMID: 21588963
16.  tert-Butyl 4-{[5-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}piperazine-1-carboxyl­ate 
In the title pyrazole derivative, C25H26ClFN4O3, both benzene rings are twisted out of the plane through the pyrazole ring, with dihedral angles of 67.62 (10) and 27.63 (10)° for the fluoro- and chloro-substituted rings, respectively. The dihedral angle between the two benzene rings is 64.54 (9)°. The piperazine ring (with a chair conformation) is linked to the pyrazole ring via a carbonyl spacer and is orientated to lie to one side of the pyrazole plane. In addition to an intra­molecular C—H⋯N contact, there are inter­molecular C—H⋯O inter­actions, which generate a supra­molecular chain with an undulating topology along the c axis that is sustained by alternating centrosymmetric ten-membered {⋯HCNCO}2 and {⋯HC3O}2 synthons.
doi:10.1107/S1600536810038560
PMCID: PMC2983130  PMID: 21587650
17.  4-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}-N-(4-cyano­phen­yl)piperazine-1-carboxamide 
In the title compound, C28H22ClFN6O2, the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyano­phenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro- and chloro­phenyl rings are 34.16 (10) and 73.27 (12)°, respectively. In the crystal, inter­molecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into sheets parallel to the ac plane.
doi:10.1107/S1600536810036159
PMCID: PMC2983346  PMID: 21587549
18.  4-{2-[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]thia­zol-4-yl}benzonitrile 
The asymmetric unit of the title compound, C25H14ClFN4S, contains two independent mol­ecules (A and B). Each mol­ecule consists of five rings, namely chloro­phenyl, fluoro­phenyl, 1H-pyrazole, thia­zole and benzonitrile. In mol­ecule A, the 1H-pyrazole ring makes dihedral angles of 52.54 (8), 35.96 (8) and 15.43 (8)° with respect to the attached chloro­phenyl, fluoro­phenyl and thia­zole rings. The corresponding values in mol­ecule B are 51.65 (8), 37.26 (8) and 8.32 (8)°. In the crystal, mol­ecules are linked into dimers by C—H⋯N hydrogen bonds, generating R 2 2(10) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the ab plane via inter­molecular weak C—H⋯N and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by weak π-π inter­actions [with centroid–centroid distances of 3.4303 (9) and 3.6826 (9) Å] and weak C—H⋯π inter­actions.
doi:10.1107/S1600536810031405
PMCID: PMC3007991  PMID: 21588640
19.  3-Ethyl-4-phen­oxy-1-(2,2,2-trifluoro­eth­yl)-1H-pyrazol-5-ol 
The title compound, C13H13F3N2O2, crystallizes with two independent mol­ecules in the asymmetric unit, with different conformations of their ethyl side chains. The dihedral angles formed between the 1H-pyrazole and benzene rings in the two mol­ecules are 79.44 (6) and 77.81 (6)°. In the crystal, mol­ecules are linked by O⋯H—N hydrogen bonds into chains propagating along [001] and the packing is further stabilized by π–π inter­actions [centroid–centroid separations = 3.5409 (10) and 3.6335 (10) Å].
doi:10.1107/S1600536810025948
PMCID: PMC3007551  PMID: 21588264
20.  4-Methyl-5-phenyl-1H-pyrazol-3-ol 
The title compound, C10H10N2O, crystallizes with two independent mol­ecules in the asymmetric unit, having closely comparable geometries. The dihedral angles between the 1H-pyrazole and benzene rings in the two mol­ecules are 39.57 (14) and 41.95 (13)°. The two mol­ecules are each connected to neighbouring mol­ecules by pairs of inter­molecular O—H⋯N hydrogen bonds, forming dimers with R 2 2(8) ring motifs. These dimers are further linked into R 4 4(10) ring motifs by inter­molecular N—H⋯O hydrogen bonds, forming chains along [101]. The crystal structure is further stabilized by a C—H⋯π inter­action.
doi:10.1107/S1600536810022828
PMCID: PMC3006807  PMID: 21587918
21.  5-Pentyl-4-phenyl­sulfonyl-1H-pyrazol-3-ol 
In the title compound, C14H18N2O3S, the 1H-pyrazole ring is approximately planar, with a maximum deviation of 0.005 (1) Å. The dihedral angle formed between the 1H-pyrazole and phenyl rings is 79.09 (5)°. Pairs of inter­molecular N—H⋯O and O⋯H⋯N hydrogen bonds form dimers between neighboring mol­ecules, generating R 2 2(10) ring motifs. These dimers are further linked by intermolecular N—H⋯O and O—H⋯N hydrogen bonds into two-dimensional arrays parallel to the ac plane. The crystal structure is also stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536810019458
PMCID: PMC2979633  PMID: 21579547
22.  5-Ethyl-4-methyl-1H-pyrazol-3(2H)-one 
In the title compound, C6H10N2O, the 2,3-dihydro-1H-pyrazole ring is approximately planar, with a maximum deviation of 0.013 (1) Å. Pairs of inter­molecular N—H⋯O hydrogen bonds link neighboring mol­ecules into dimers, generating R 2 2(8) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the bc plane by inter­molecular N—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S160053681001696X
PMCID: PMC2979558  PMID: 21579442
23.  N,N′-Bis(4-fluoro­phen­yl)urea 
The asymmetric unit of the title compound, C13H10F2N2O, contains one and a half N,N′-bis­(4-fluoro­phen­yl)urea mol­ecules. One of the mol­ecules has crystallographic twofold rotation symmetry. The benzene rings are twisted from each other by dihedral angles of 29.69 (6)° for the mol­ecule in a general position and 89.83 (6)° for the symmetry-generated mol­ecule. In the crystal structure, a pair of inter­molecular N—H⋯O hydrogen bonds link symmetry-related mol­ecules into chains along the b axis, forming R 2 1(6) ring motifs.
doi:10.1107/S1600536810016399
PMCID: PMC2979587  PMID: 21579412
24.  Tert-butyl 3-oxo-2,3,4,5,6,7-hexa­hydro-1H-pyrazolo[4,3-c]pyridine-5-carboxyl­ate 
In the title compound, C11H17N3O3, the pyrazole ring is approximately planar, with a maximum deviation of 0.005 (2) Å, and forms a dihedral angle of 5.69 (13)° with the plane through the six atoms of the piperidine ring. In the crystal, pairs of inter­molecular N—H⋯O hydrogen bonds form dimers with neighbouring mol­ecules, generating R 2 2(8) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the bc plane by inter­molecular N—H⋯O and C—H⋯O hydrogen bonds.
doi:10.1107/S1600536809053021
PMCID: PMC2980051  PMID: 21580034
25.  5-Methoxy­methyl-4-phen­oxy-1H-pyrazol-3-ol 
In the title compound, C11H12N2O3, the pyrazole ring system is essentially planar [maximum deviation = 0.002 (2) Å] and forms a dihedral angle of 66.93 (9)° with the benzene ring. In the crystal packing, pairs of inter­molecular N—H⋯O and O—H⋯N hydrogen bonds connect neighbouring mol­ecules into dimers, generating R 2 2(10) and R 2 2(8) ring motifs, respectively. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536809050302
PMCID: PMC2971925  PMID: 21578948

Results 1-25 (25)