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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.  (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
5.  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
6.  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
7.  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
8.  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
9.  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
10.  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
11.  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
12.  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
13.  1-(4-Chloro­phen­yl)-2-[4-hy­droxy-3-(3-meth­oxy­benzo­yl)-1,1-dioxo-2H-1λ6,2-benzothia­zin-2-yl]ethanone 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.406 (5) and 0.444 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The meth­oxy­benzoyl and the chloro­phenyl rings lie roughly parallel to each other, with a dihedral angle between the mean planes of these rings of 8.86 (10)°. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯O inter­actions and the crystal packing is stabilized by inter­molecular O—H⋯O and C—H⋯Cl hydrogen bonds.
doi:10.1107/S160053681201029X
PMCID: PMC3344017  PMID: 22589926
14.  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
15.  [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
16.  N-[2-({[1-(4-Chloro­phen­yl)-1H-pyrazol-3-yl]­oxy}meth­yl)phen­yl]-N-meth­oxy­hydrazinecarboxamide 
In the title compound, C18H18ClN5O3, the hydrazinecarboxamide N—N—C(O)—N unit is nearly planar [maximum deviation = 0.074 (2) Å] and is inclined at a dihedral angle of 57.43 (7)° with respect to the plane of the attached benzene ring. The chloro­phenyl group makes dihedral angles of 19.71 (7) and 34.07 (6)° with the pyrazole and benzene rings, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers that are further linked into chains along the a-axis direction by N—H⋯N hydrogen bonds. In addition, π–π stacking inter­actions are observed between benzene rings [centroid–centroid distance = 3.680 (1) Å].
doi:10.1107/S1600536812038214
PMCID: PMC3470263  PMID: 23125707
17.  1-[6-Chloro-4-(2-chloro­phen­yl)-2-methyl-3-quinol­yl]ethanone 
The title compound, C18H13Cl2NO, features an essentially planar quinoline ring system (r.m.s. deviation = 0.023 Å) with the acetyl [C—C—C—O torsion angle = −78.27 (17)°] and benzene [C—C—C—C torsion angle = 110.11 (14)°] substituents being twisted out of the plane; the dihedral angle formed between the mean planes of these two substituents is 58.01 (8)°. The acetyl O and benzene-bound Cl atoms lie to opposite sides of the mol­ecule. Centrosymmetric aggregates mediated by pairs of C—H⋯O contacts are found in the crystal structure, and these are connected into a two-dimensional array in the (01) plane via Cl⋯O [3.0508 (11) Å] inter­actions.
doi:10.1107/S1600536810026991
PMCID: PMC3007567  PMID: 21588316
18.  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
19.  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
20.  2,3-Dibromo-3-(4-chloro­phen­yl)-1-(2-hy­droxy­phen­yl)propan-1-one 
In the title mol­ecule, C15H11Br2ClO2, an S(6) ring motif is formed via an intra­molecular O—H⋯O hydrogen bond. The dihedral angle formed between the chloro- and hy­droxy-substituted benzene rings is 34.10 (15)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis.
doi:10.1107/S1600536811036798
PMCID: PMC3201456  PMID: 22064869
21.  3-(4-Chloro­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
In the title compound, C16H11ClN2O, the chloro-substituted phenyl ring is disordered over two positions with refined site occupancies of 0.503 (2) and 0.497 (2). The dihedral angle between the pyrazole and phenyl rings is 7.93 (7)°. The pyrazole ring also forms dihedral angles of 24.43 (9)° and 28.67 (9)° with the disordered chloro-substituted benzene ring. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds, generating R 2 1(7) and R 2 2(10) ring motifs. π–π inter­actions between the pyrazole and phenyl rings [centroid–centroid distance = 3.758 (1) Å] further stabilize the crystal structure.
doi:10.1107/S1600536811023713
PMCID: PMC3151838  PMID: 21837157
22.  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
23.  2-Amino-4-(4-chloro­phen­yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile propan-2-one monosolvate 
In the title compound, C18H17ClN2O2·C3H6O, the 4H-pyran ring is nearly planar [maximum deviation = −0.108 (1) Å] and the cyclo­hexene ring is puckered [puckering parameters Q T = 0.4596 (17) Å, θ = 55.9 (2)° and ϕ = 226.5 (3)°]. The 4H-pyran ring is approximately perpendicular to the benzene ring [dihedral angle = 84.35 (7)°] and is almost coplanar with the mean plane of the cyclo­hexene ring [dihedral angle = 8.64 (7)°]. In the crystal, inversion-related main mol­ecules are linked into dimers by pairs of N—H⋯N hydrogen bonds, generating an R 2 2(12) graph-set motif. These dimers are further connected by N—H⋯O and C—H⋯N hydrogen bonds, forming a layer structure extending parallel to the (011) plane. In addition, the mol­ecules within the layers inter­act with each other via C—H⋯π inter­actions.
doi:10.1107/S1600536812024142
PMCID: PMC3379514  PMID: 22719712
24.  2-[(2-Chloro­phen­yl)(hy­droxy)meth­yl]phenol 
In the title compound, C13H11ClO2, the dihedral angle between the mean planes of the 2-chloro­phenyl and phenol rings is 87.4 (9)°. The methyl hy­droxy group lies nearly perpendicular to the plane of its attached benzene ring [O—C—C—C torsion angle = 84.3 (3)°]. The two hy­droxy groups lie on the same side of the mol­ecule and are in a slightly twisted gauche conformation [O—C—C—O torsion angle = 77.1 (8)°] to each other. In the crystal, O—H⋯O hydrogen bonds between nearby methyl­hydroxy groups form dimers in alternating pairs aligned diagonally along the b axis. A view along the c axis reveals a hexa­meric aggregate mediated by a ring of six O—H⋯O hydrogen bonds generating an R 6 6(12) motif loop.
doi:10.1107/S1600536813018667
PMCID: PMC3793743  PMID: 24109330
25.  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

Results 1-25 (460108)