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1.  1-[3-(4-Chloro­phen­yl)-5-(4-meth­oxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title compound, C18H17ClN2O2, the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, mol­ecules are linked via bifurcated (C,C)–H⋯O hydrogen bonds into chains along [010]. The crystal structure is further consolidated by C—H⋯π inter­actions.
doi:10.1107/S1600536812009439
PMCID: PMC3343987  PMID: 22589896
2.  1-[5-(4-Chloro­phen­yl)-3-(4-hy­droxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]­ethanone 
In the title compound, C17H15ClN2O2, the benzene rings form dihedral angles of 89.56 (5) and 5.87 (5)° with the mean plane of the pyrazoline ring (r.m.s. deviation = 0.084 Å). The dihedral angle between the two benzene rings is 87.57 (5)°. In the crystal, mol­ecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a helical chain along the c axis. Between the chains weak C—H⋯N and C—H⋯O inter­actions are present. The crystal studied was an inversion twin with a domain ratio of 0.72 (4):0.28 (4).
doi:10.1107/S1600536812006885
PMCID: PMC3297879  PMID: 22412682
3.  10-(4-Chloro­phen­yl)-14a-hy­droxy-12-methyl-8,9,9a,10,12,13,14,14a-octa­hydro-5H-10a,14-methano­indeno­[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione 
The asymmetric unit of the title compound, C26H25ClN2O3, contains two independent mol­ecules (A and B). The conformation of the two mol­ecules differs essentially in the dihedral angle involving the two benzene rings. They are inclined to one another by 52.47 (10) in A and by 31.75 (11)° in B. In both mol­ecules, the six-membered piperidin-3-one rings have chair conformations. In mol­ecule A, all four five-membered rings have twist conformations. In mol­ecule B, only three of the four five-membered rings have twist conformations. The fourth, of the inden-1-one moiety, has an envelope conformation with the spiro C atom, bonded to the N atom of the pyrrolidine ring, as the flap. A weak intra­molecular O—H⋯N hydrogen bond occurs in each independent mol­ecule while a C—H⋯O inter­action is also observed in mol­ecule A. In the crystal, pairs of O—H⋯O hydrogen bonds link the mol­ecules, forming inversion dimers with graph-set motif R 2 2(12). These dimers are further inter­connected by C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.
doi:10.1107/S1600536813034107
PMCID: PMC3914117  PMID: 24527024
4.  3-(4-Chloro­phen­yl)-5-(4-eth­oxy­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide ethanol monosolvate 
The asymmetric unit of the title compound, C18H18ClN3OS·C2H5OH, comprises a pyrazoline derivative and an ethanol solvent mol­ecule. In the mol­ecule of the pyrazoline derivative, the pyrazole ring adopts an envelope conformation with the C atom bearing the eth­oxy­phenyl substituent as the flap. The dihedral angle between the benzene rings is 74.22 (7)°. The eth­oxy group is coplanar with the attached benzene ring [C—O—C—Cmeth­yl = 175.50 (11)° and r.m.s. deviation = 0.0459 (1) Å for the nine non-H atoms]. In the crystal, the pyrazoline mol­ecules are linked by N—H⋯Oeth­oxy hydrogen bonds into chains along the c axis and are further linked with the solvent ethanol mol­ecules by N—H⋯Oethanol and Oethanol—H⋯S hydrogen bonds. C—H⋯π inter­actions are also present.
doi:10.1107/S1600536813005369
PMCID: PMC3629506  PMID: 23634024
5.  Diethyl 4-[5-(4-chloro­phen­yl)-1H-pyrazol-4-yl]-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate 
In the title compound, C22H24ClN3O4, intra­molecular C—H⋯O and C—H⋯N hydrogen bonds form S(9) and S(7) ring motifs, respectively. The 1,4-dihydro­pyridine ring adopts a flattened boat conformation. The benzene ring makes a dihedral angle of 33.36 (6)° with the pyrazole ring. In the crystal, pairs of N—H⋯N hydrogen bonds link the mol­ecules into inversion dimers. The dimers are stacked in column along the a axis through N—H⋯O and C—H⋯N hydrogen bonds. The crystal packing also features C—H⋯π inter­actions involving the pyrazole ring.
doi:10.1107/S160053681201344X
PMCID: PMC3344438  PMID: 22590200
6.  2-Amino-4-(4-chloro­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbonitrile–3-amino-1-(4-chloro­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (1/4) 
The asymmetric unit of the 1:4 title co-crystal of 2-amino-4-(4-chloro­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbonitrile and 3-amino-1-(4-chloro­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile, 0.2C20H14ClN3·0.8C22H14ClN3, has the atoms of the fused-ring system and those of the amino, cyano and chloro­phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl­ene linkage in the central ring. There are two independent overlapped mol­ecules in the asymmetric unit. In one independent mol­ecule, the two flanking aromatic rings are twisted by 24.4 (1)° and the ring of the chloro­phenyl substituent is twisted by 87.3 (1)° relative to the amino- and cyano-bearing aromatic ring. In the second mol­ecule, the respective dihedral angles are 26.1 (1) and 57.8 (1)°. The two independent mol­ecules are linked by N—H⋯N hydrogen bonds into dimers.
doi:10.1107/S1600536811040529
PMCID: PMC3247609  PMID: 22219914
7.  1-[3-(4-Chloro­phen­yl)-5-(4-meth­oxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]butan-1-one 
In the title compound, C20H21ClN2O2, the benzene rings form dihedral angles of 6.35 (5) and 81.82 (5)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.145 Å). This latter ring adopts an envelope conformation with the CH grouping as the flap. The dihedral angle between the benzene rings is 75.63 (4)°. In the crystal, mol­ecules are linked by C—H⋯Cl and C—H⋯O hydrogen bonds into chains along [-201]. The crystal structure also features C—H⋯π inter­actions.
doi:10.1107/S1600536812009105
PMCID: PMC3343949  PMID: 22590030
8.  1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}propan-1-one 
In the title compound, C21H23ClN2O, the dihedral angle between the benzene rings is 83.2 (6)°, while the mean plane of the pyrazole ring [r.m.s. deviation = 0.043 (1) Å] makes dihedral angles of 3.4 (3) and 86.2 (1)° with the benzene rings. In the crystal, a pair of weak C—H⋯O inter­actions between the benzene ring and the propan-1-one group link the mol­ecules into an inversion dimer with an R 2 2(16) graph-set motif. In addition, a weak π–π stacking inter­action [centroid–centroid distance = 3.959 (4) Å] connects the dimers into a tape running along [201].
doi:10.1107/S1600536814013075
PMCID: PMC4120579  PMID: 25161555
9.  1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}ethanone 
In the title compound, C20H21ClN2O, the dihedral angles between the pyrazole ring (r.m.s. deviation = 0.049 Å) and the benzene and chloro­benzene rings are 84.65 (10) and 3.35 (10)°, respectively. In the crystal, inversion dimers linked by pairs of weak C—H⋯O inter­actions generate R 2 2(16) loops. Weak π–π stacking inter­actions [centroid–centroid distance = 3.8490 (11) Å] are also observed.
doi:10.1107/S1600536814013348
PMCID: PMC4120582  PMID: 25161567
10.  (E)-1-(4-Chloro­phen­yl)ethanone semi­carbazone 
In the title compound, C9H10ClN3O, the semicarbazone group is approximately planar, with an r.m.s. deviation from the mean plane of 0.054 (1) Å. The dihedral angle between the least-squares planes through the semicarbazone group and the benzene ring is 30.46 (5)°. In the solid state, mol­ecules are linked via inter­molecular N—H⋯O and N—H⋯N hydrogen bonds, generating R 2 2(9) ring motifs which, together with R 2 2(8) ring motifs formed by pairs of inter­molecular N—H⋯O hydrogen bonds, lead to the formation of a seldom-observed mol­ecular trimer. Furthermore, N—H⋯O hydrogen bonds form R 2 1(7) ring motifs with C—H⋯O hydrogen bonds, further consolidating the crystal structure. Mol­ecules are linked by these inter­molecular inter­actions, forming two-dimensional networks parallel to (100).
doi:10.1107/S160053680902279X
PMCID: PMC2969321  PMID: 21582900
11.  4-[2-(4-Chloro­phen­yl)hydrazinyl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title mol­ecule, C11H10ClN5OS, an intra­molecular N—H⋯O hydrogen forms an S(6) ring motif. The dihedral angle between the pyrazole ring and the benzene ring is 3.77 (8)°. In the crystal, mol­ecules are linked by N—H⋯S and N—H⋯O hydrogen bonds into layers parallel to the bc plane.
doi:10.1107/S1600536811038463
PMCID: PMC3201496  PMID: 22058802
12.  (1R*,3′S*,4′R*)-4′-(4-Chloro­phen­yl)-3′-[(4-hy­droxy-2-oxo-1,2-dihydro­quinolin-3-yl)carbon­yl]-1′-methyl­spiro­[ace­naphthyl­ene-1,2′-pyrrolidin]-2-one 
The title compound, C32H23ClN2O4, has a quinoline, a chloro­phenyl and an acenaphthalene ring system attached to a central pyrrolidine ring, which has three stereogenic centers. Nevertheless, the compound crystallizes as a racemate with two mol­ecules of identical chirality in the asymmetric unit. They differ in the conformation of the five-membered pyrrolidine ring; in one molecule it has an envelope conformation, while in the other molecule it has a twisted conformation. In each molecule there is an intra­molecular O—H⋯O hydrogen bond making an S(6) ring motif. In the crystal, pairs of N—H⋯O hydrogen bonds produce inversion dimers with R 2 2(8) motifs. There are also C—H⋯O interactions present. The crystal structure contains voids (60 Å3) within which there is no evidence of solvent mol­ecules.
doi:10.1107/S1600536811048896
PMCID: PMC3239020  PMID: 22199868
13.  2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C24H17ClFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.030 Å). With the exception of the methine-bound benzene ring, which forms a dihedral angle of 85.77 (13)° with the pyrazole ring, the remaining non-C atoms lie in an approximate plane (r.m.s. deviation = 0.084 Å) so that overall the mol­ecule has a T-shape. In the crystal, centrosymmetrically related mol­ecules are connected via π–π inter­actions between pyrazole rings [centroid–centroid distance = 3.5370 (15) Å] and these stack along the a axis with no specific inter­actions between them.
doi:10.1107/S1600536813007496
PMCID: PMC3629623  PMID: 23634110
14.  6-(4-Chloro­phen­yl)-2-(4-meth­oxy­phen­yl)-6,7-dihydro-4H-pyrazolo­[5,1-c][1,4]oxazine 
In the title compound, C19H17ClN2O2, the pyrazole ring is almost planar with a maximum deviation of 0.009 (3) Å and makes a dihedral angle of 8.96 (9)° with the oxazine ring. The dihedral angles between the pyrazole ring and the chlorine- and meth­oxy-substituted benzene rings are 50.95 (8) and 13.24 (9)°, respectively. An inter­molecular C—H⋯N hydrogen bond links the mol­ecules into infinite chains along the a axis. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811025906
PMCID: PMC3212334  PMID: 22090991
15.  2-(1H-1,3-Benzodiazol-2-ylsulfan­yl)-1-(4-chloro­phen­yl)ethanone 
The mol­ecule in the structure of the title compound, C15H11ClN2OS, displays two planar residues [r.m.s. deviation = 0.014 Å for the benzimidazole residue, and the ketone group is co-planar with the benzene ring to which it is attached forming a O—C—C—C torsion angle of −173.18 (14) °] linked at the S atom. The overall shape is based on a twisted V, the dihedral angle formed between the two planes being 82.4 (2) °. The amine-H atom is bifurcated, forming N—H⋯O and N—H⋯S hydrogen bonds leading to dimeric aggregates. These are linked into a supra­molecular chain along the c axis via C—H⋯π hydrogen bonds. Chains form layers in the ab plane being connected along the c axis via weak π–π inter­actions [3.9578 (8) Å] formed between centrosymmetrically related chloro-substituted benzene rings.
doi:10.1107/S160053681103666X
PMCID: PMC3201531  PMID: 22064924
16.  3-[5-(4-Chloro­phen­yl)-1-(4-methoxy­phen­yl)-1H-pyrazol-3-yl]propionic acid and the corresponding methyl ester 
The synthesis of 3-[5-(4-chloro­phen­yl)-1-(4-methoxy­phen­yl)-1H-pyrazol-3-yl]propionic acid, C19H17ClN2O3, (I), and its corresponding methyl ester, methyl 3-[5-(4-chloro­phen­yl)-1-(4-methoxy­phen­yl)-1H-pyrazol-3-yl]propionate, C20H19ClN2O3, (II), is regiospecific. However, correct identification of the regioisomer formed by spectroscopic techniques is not trivial and single-crystal X-ray analysis provided the only means of unambiguous structure determination. Compound (I) crystallizes with Z′ = 2. The propionic acid groups of the two crystallographically unique mol­ecules form a hydrogen-bonded dimer, as is typical of carboxylic acid groups in the solid state. Conformational differences between the meth­oxy­benzene and pyrazole rings give rise to two unique mol­ecules. The structure of (II) features just one mol­ecule in the asymmetric unit and the crystal packing makes greater use than (I) of weak C—H⋯A inter­actions, despite the lack of any functional groups for classical hydrogen bonding.
doi:10.1107/S010827010900941X
PMCID: PMC2724994  PMID: 19346614
17.  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
18.  Crystal structure of (3,5-di­chloro-2-hy­droxy­phen­yl){1-[(naphthalen-1-yl)carbon­yl]-1H-pyrazol-4-yl}methanone 
The title compound is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. In the crystal, mol­ecules are linked through stacking inter­actions between the pyrazole rings and between the naphthalene and phenyl rings, and through inter­molecular C—H⋯O hydrogen bonds to form inversion dimers.
The title compound, C21H12Cl2N2O3, is a 1,4-diaroyl pyrazole derivative and has three aromatic rings. The dihedral angles between the naphthalene ring system and the pyrazole ring, the pyrazole and phenyl rings and the naphthalene ring system and the phenyl ring are 49.44 (13), 49.87 (16) and 0.58 (11)°, respectively. The phenolic proton forms an intra­molecular O—H⋯O hydrogen bond with an adjacent carbonyl O atom. In the crystal, the mol­ecules are linked through stacking inter­actions between the pyrazole rings [centroid–centroid distances = 3.546 (3)] and between the naphthalene ring system and the phenyl ring [centroid–centroid distances = 3.609 (4) Å] along the a-axis direction. The mol­ecules are further connected through C—H⋯O hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536814024684
PMCID: PMC4257447  PMID: 25552982
crystal structure; diaroyl pyrazole; cyclization; stacking inter­action; C—H⋯O hydrogen bonding
19.  1-{3-(4-Chloro­phen­yl)-5-[4-(propan-2-yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl}butan-1-one 
In the title compound, C22H25ClN2O, the pyrazole ring exhibits an envelope conformation with the methine C atom as the flap. The benzene rings are twisted by 3.3 (5) and 84.6 (5)° from the pyrazole mean plane, and are inclined to each other by 81.4 (4)°. In the crystal, pairs of weak C—H⋯O hydrogen bonds form centrosymmetric dimers with an R 2 2(16) graph-set motif. C—H⋯π inter­actions link the dimers into columns propagating in [100].
doi:10.1107/S1600536814013063
PMCID: PMC4120539  PMID: 25161554
20.  [1-(4-Chloro­phen­yl)-5-hy­droxy-3-phenyl-1H-pyrazol-4-yl](thio­phen-2-yl)methanone 
In the title compound, C20H13ClN2O2S, the chloro­phenyl, phenyl and thienoyl rings are oriented at dihedral angles 17.84 (7), 53.13 (8) and 34.03 (8)°, respectively, to the central pyrazole ring. An intra­molecular O—H⋯O hydrogen bond occurs. In the crystal, pairs of bifurcated O—H⋯O hydrogen bonds link mol­ecules into inversion dimers with R 2 2(12) graph-set motifs.
doi:10.1107/S1600536812019253
PMCID: PMC3379242  PMID: 22719440
21.  4′-(4-Chloro­phen­yl)-3′-(4-meth­oxy­phen­yl)-3,4-dihydro-1H,4′H-spiro­[acridine-2,5′-isoxazol]-1-one 
In the title compound, C28H21ClN2O3, the quinoline ring system is essentially planar with a maximum deviation of 0.0436 (17) Å. The isoxazole and cyclo­hexane rings adopt envelope conformations. The isoxazole ring is almost orthogonal to both the quinoline ring system and the cyclo­hexane ring, making dihedral angles of 85.75 (8) and 81.46 (9) °, respectively. The O atom deviates signifigantly from the six-membered carbocyclic ring by 0.3947 (16) Å. In the crystal, mol­ecules are linked into inversion dimers via pairs of C—H⋯O inter­actions, resulting in R 2 2(24) ring motifs.
doi:10.1107/S1600536812042523
PMCID: PMC3515270  PMID: 23284490
22.  3-[4-Amino-3-(4-methyl­phen­yl)-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-3-(2-chloro­phen­yl)-1-phenyl­propan-1-one 
In the title mol­ecule, C24H21ClN4OS, the 1,2,4-triazole ring forms dihedral angles of 37.2 (2), 71.9 (2) and 84.9 (2) ° with the three benzene rings. In the crystal, weak inter­molecular N—H⋯S hydrogen bonds link the mol­ecules into centrosymmetric dimers.
doi:10.1107/S1600536811023993
PMCID: PMC3151860  PMID: 21837166
23.  Crystal structure of (4Z)-1-(3,4-di­chloro­phen­yl)-4-[hy­droxy(4-methyl­phen­yl)methyl­idene]-3-methyl-4,5-di­hydro-1H-pyrazol-5-one 
The title compound, C18H14Cl2N2O2, crystallizes with two mol­ecules, A and B, in the asymmetric unit. In mol­ecule A, the dihedral angles between the central pyrazole ring and pendant di­chloro­benzene and p-tolyl rings are 2.18 (16) and 46.78 (16)°, respectively. In mol­ecule B, the equivalent angles are 27.45 (16) and 40.45 (18)°, respectively. Each mol­ecule features an intra­molecular O—H⋯O hydrogen bond, which closes an S(6) ring and mol­ecule A also features a C—H⋯O inter­action. In the crystal, weak C—H⋯π interactions and aromatic π–π stacking [shortest centroid–centroid separation = 3.707 (2) Å] generate a three-dimensional network.
doi:10.1107/S160053681402114X
PMCID: PMC4257223  PMID: 25484715
crystal structure; Schiff-base pyrazole derivative; hydrogen bonding; C—H⋯π inter­actions; aromatic π–π stacking
24.  3-(3-Chloro-2-hy­droxy­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
In the title compound, C16H11ClN2O2, the pyrazole ring makes dihedral angles of 11.88 (13) and 22.33 (13)° with the 3-chloro-2-hy­droxy­benzene group and phenyl rings, respectively. The phenolic hy­droxy group forms an intra­molecular O—H⋯N hydrogen bond with the imine N atom of the pyrazole unit. The formyl group is virtually coplanar with the pyrazole ring [dihedral angle = 4.5 (19)°] and acts as an acceptor in an intra­molecular C—H⋯O hydrogen bond closing seven-membered ring. In the crystal, adjacent mol­ecules are linked through C—H⋯O hydrogen bonds into infinite chains along the b axis.
doi:10.1107/S1600536811038025
PMCID: PMC3201353  PMID: 22058800
25.  6-(2-Chloro­benz­yl)-1-(4-chloro­phen­yl)-7-hy­droxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one 
The title compound, C19H15Cl2N3O2, was obtained by a one-step cyclo­condensation of 2-amino-1-(4-chloro­phen­yl)imidazoline with diethyl (2-chloro­benz­yl)malonate under basic conditions. In the crystalline state, the mol­ecule exists as the 7-hy­droxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chloro­phenyl and chloro­benzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the mol­ecule is influenced by the intra­molecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π inter­actions [centroid–centroid distance = 3.6707 (12) Å].
doi:10.1107/S160053681003919X
PMCID: PMC3009369  PMID: 21588948

Results 1-25 (456420)