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1.  1-[5-(2-Chloro­phen­yl)-5-hy­droxy-3-methyl-4,5-dihydro-1H-pyrazol-1-yl]­ethanone 
The title compound, C12H13ClN2O2, crystallizes with two independent but very similar mol­ecules (A and B) in the asymmetric unit. The pyrazole ring in each mol­ecule has an envelope conformation. The dihedral angle between the pyrazole ring mean plane and the benzene ring is 86.07 (14)° in A and 85.99 (14)° in B. In the crystal, the A and B mol­ecules are linked via a pair of O—H⋯O hydrogen bonds, forming dimers. These dimers are further linked via C—H⋯O inter­actions to form –A–B–A–B– chains propagating along the c-axis direction.
doi:10.1107/S1600536812007283
PMCID: PMC3297897  PMID: 22412700
2.  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
3.  Crystal structure of N-[3-(2-chloro­benzo­yl)-5-ethyl­thio­phen-2-yl]-2-[(E)-(2-hy­droxy­benzyl­idene)amino]­acetamide 
In the title compound, C22H19ClN2O3S, the dihedral angle between the mean planes of the thio­phene ring and the chloro­phenyl and hy­droxy­phenyl rings are 70.1 (1) and 40.2 (4)°, respectively. The benzene rings are twisted with respect to each other by 88.9 (3)°. The imine bond lies in an E conformation. Intra­molecular O—H⋯N and N—H⋯O hydrogen bonds each generate S(6) ring motifs. In the crystal, weak C—H⋯O inter­actions link the mol­ecules, forming chains along the c axis and zigzag chains along the b axis, generating sheets lying parallel to (100).
doi:10.1107/S1600536814018224
PMCID: PMC4186110  PMID: 25309197
crystal structure; thio­phene derivatives; Schiff bases; hydrogen bonding
4.  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
5.  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
6.  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
7.  (2E)-3-(4-Chloro­phen­yl)-1-(4-hy­droxy­phen­yl)prop-2-en-1-one 
In the title compound, C15H11ClO2, the dihedral angle between the mean planes of the chloro­benzene and hy­droxy­benzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hy­droxy­phenyl ring and 11.5 (1)° with the chloro­phenyl ring. The crystal packing is stabilized by inter­molecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].
doi:10.1107/S160053681100701X
PMCID: PMC3099984  PMID: 21754053
8.  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
9.  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
10.  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
11.  [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
12.  3-(4-Chloro­phen­yl)-5-(thio­phen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title pyrazoline derivative, C14H12ClN3S2, the thiophene ring is disordered over two orientations with a refined site-occupancy ratio of 0.832 (4):0.168 (4). The pyrazoline ring adopts an envelope conformation with the C atom linking the thiophene ring at the flap. The dihedral angles between the benzene ring and the major and minor components of the thiophene ring are 88.6 (3) and 85.6 (15)°, respectively while the dihedral angle between the disorder components of the ring is 3.1 (16)°. The mean plane of the pyrazoline ring makes dihedral angles of 11.86 (13), 80.1 (3) and 83.0 (15)°, respectively, with the benzene ring, and the major and minor components of the thiophene ring. An intra­molecular N(amide)—H⋯N(pyrazoline) hydrogen bond generates an S(5) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯S and N(amide)—H⋯S inter­actions into a tape along [10]. C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536811054754
PMCID: PMC3274952  PMID: 22346905
13.  Crystal structure of (4Z)-4-[(2E)-3-(2-chloro­phen­yl)-1-hy­droxy­prop-2-en-1-yl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 
In the title compound, C19H15ClN2O2, the pyrazole ring is almost planar (r.m.s. deviation = 0.002 Å) and subtends dihedral angles of 5.31 (16) and 1.86 (16)° with the phenyl and chloro­benzene rings, respectively. An intra­molecular O—H⋯O hydrogen bond closes an S(6) ring and a short C—H⋯O contact is also observed. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions to generate (001) sheets. Weak aromatic π–π inter­actions between the chloro­benzene and pyrazole rings, with a centroid–centroid distance of 3.7956 (17) Å are also observed.
doi:10.1107/S2056989015009020
PMCID: PMC4459312  PMID: 26090193
crystal structure; pyrazole; hydrogen bonding; π–π inter­actions
14.  1-[5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title mol­ecule, C17H14BrFN2O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into corrugated layers parallel to the ab plane.
doi:10.1107/S1600536812033351
PMCID: PMC3415024  PMID: 22905011
15.  2-(1-Adamant­yl)-1-{4-[(2-chloro-9-isopropyl-9H-purin-6-yl)amino­meth­yl]phen­yl}ethanone 
The structure of the title compound, C27H32ClN5O, consists of two crystallographically independent conformers differing slightly in all geometric parameters. Both contain nearly planar purine and benzene ring systems [maximum deviations of 0.046 (3) and 0.005 (2) Å, respectively], the dihedral angles between them being 76.44 (6) and 82.39 (6)°, and an adamantane cage consisting of three fused cyclo­hexane rings in almost ideal chair conformations, with C—C—C angles in the range 108.7 (2)–110.6 (2)°. The carbonyl plane and the benzene ring are almost coplanar [dihedral angles of 6.43 (9) and 0.64 (8)° in the two conformers]. The crystal structure is stabilized by inter­molecular N—H⋯N inter­actions that link adjacent mol­ecules into dimers and by some non-bonding contacts of the C—H⋯Cl type.
doi:10.1107/S160053680900052X
PMCID: PMC2968337  PMID: 21581908
16.  1-[2-(4-Chloro­phen­yl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone 
In the title compound, C16H14ClN3O2, the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π–π [centroid–centroid distance = 3.7311 (6) Å] and C—H⋯π inter­actions are observed.
doi:10.1107/S1600536812023100
PMCID: PMC3379458  PMID: 22719656
17.  (3R*,4R*)-1-(4-Chloro­phen­yl)-4-[2-hy­droxy-3-(morpholinomethyl)­phen­yl]-3-phen­oxy­azetidin-2-one 
The β-lactam ring of the title compound, C26H25ClN2O4, is nearly planar (r.m.s. deviation = 0.025 Å) and the morpholine ring adopts a chair conformation. The mean plane of the β-lactam ring makes dihedral angles of 21.6 (4), 84.4 (4) and 33.7 (4)° with the two benzene rings and the phenyl ring, respectively. The conformation of the title compound is stabilized by intra­molecular C—H⋯O and O—H⋯N inter­actions. The crystal structure features C—H⋯π and aromatic π–π stacking inter­actions [centroid–centroid distances = 3.684 (4) and 3.883 (4) Å].
doi:10.1107/S1600536811000675
PMCID: PMC3051698  PMID: 21523011
18.  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
19.  1-[3,5-Bis(4-chloro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title compound, C17H14Cl2N2O, the dihedral angles between the pyrazole ring and the mean planes of the benzene and chloro-substituted benzene rings are 75.97 (1) and 16.63 (1)° respectively. In the crystal, two weak C—H⋯O inter­molecular hydrogen bonds and π–π stacking inter­actions [centroid–centroid distances = 3.774 (4) and 3.716 (7) Å] are observed.
doi:10.1107/S1600536810025584
PMCID: PMC3007262  PMID: 21588275
20.  (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
21.  N-(4-Chloro­phen­yl)-5-(4,5-dihydro-1H-imidazol-2-yl)thieno[2,3-b]pyridin-4-amine 
In the title compound, C16H13ClN4S, the thienopyridine fused-ring system is nearly planar (r.m.s. deviation = 0.0333 Å) and forms a dihedral angle of 4.4 (3)° with the attached dihydro­imidazole ring (r.m.s. deviation = 0.0429 Å) allowing for the formation of an intra­molecular (exocyclic amine)N—H⋯N(imine) hydrogen bond. The benzene rings of the disordered (50:50) –N(H)—C6H4Cl residue form dihedral angles of 59.1 (3) and 50.59 (15)° with the fused ring system. In the crystal, (imidazole amine)N—H⋯N(pyridine) hydrogen bonds lead to a supra­molecular helical chain along the b axis. The chains assemble into layers (ab plane) with inter-digitation of the chloro­benzene rings which results in weak C—H⋯Cl inter­actions in the c-axis direction.
doi:10.1107/S160053681202658X
PMCID: PMC3393946  PMID: 22798811
22.  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
23.  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
24.  1-[4-(4-Hy­droxy­phen­yl)piperazin-1-yl]ethanone 
In the title compound, C12H16N2O2, the piperazine ring has a chair conformation. The dihedral angle between the mean planes of the benzene ring and the acetyl group is 48.7 (1)°. In the crystal, mol­ecules are linked via O—H⋯O hydrogen bonds, forming chains propagating along [010].
doi:10.1107/S1600536813028031
PMCID: PMC3884329  PMID: 24454105
25.  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

Results 1-25 (157990)