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1.  1-[3-(2,4-Dichloro-5-fluoro­phen­yl)-5-(3-methyl-2-thien­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title mol­ecule, C16H13Cl2FN2OS, the dihedral angle between the thio­phene and benzene rings is 80.34 (12)°. The pyrazoline ring is in an envelope conformation, and the plane through the four coplanar atoms makes dihedral angles of 85.13 (9) and 6.89 (10)° with the thio­phene and benzene rings, respectively. The C and O atoms of the acetyl group are nearly coplanar with the attached pyrazoline ring. In the crystal structure, inversion dimers arise from pairs of inter­molecular C—H⋯O hydrogen bonds. A short inter­molecular Cl⋯S contact of 3.4250 (13) Å is also found.
doi:10.1107/S1600536808033837
PMCID: PMC2959565  PMID: 21581020
2.  N-(2-Nitro­phen­yl)benzamide 
In the title compound, C13H10N2O3, the central C–C(=O)–N–C amide unit makes dihedral angles of 21.68 (4) and 19.08 (4)°, respectively, with the phenyl and nitro­benzene rings. The two aromatic rings are inclined at 3.74 (3)° and the nitro group is skewed out of the attached benzene ring plane by 18.55 (8)°. An intra­molecular N—H⋯O inter­action to an O atom of the nitro substituent generates an S(6) ring motif. In the crystal, C—H⋯O contacts generate two centrosymmetric ring systems with R 2 2(14) and R 2 2(20) graph-set motifs, forming zigzag chains down the a axis. π–π inter­actions between adjacent phenyl and nitro­benzene rings [centroid–centroid distance = 3.6849 (6) Å] also form centrosymmetric dimers. These and an additional C—H⋯O hydrogen bond generate an extensive three-dimensional network structure.
doi:10.1107/S1600536809024271
PMCID: PMC2977104  PMID: 21583545
3.  (4-Chloro­phen­yl)[1-(4-methoxy­phen­yl)-3-(5-nitro-2-fur­yl)-1H-pyrazol-4-yl]methanone 
In the title compound, C21H14ClN3O5, an intra­molecular C—H⋯O hydrogen bond generates an S(7) ring motif and the furan and pyrazole rings are almost coplanar, making a dihedral angle of 1.98 (5)°. The pyrazole ring is inclined at dihedral angles of 47.59 (4) and 7.27 (4)° to the chloro­phenyl and methoxy­phenyl groups, respectively. The nitro group is almost coplanar to its attached furan ring [dihedral angle = 2.03 (12)°]. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal structure also features short inter­molecular O⋯N [2.8546 (12) Å] and Cl⋯O [3.0844 (9) Å] contacts as well as aromatic π–π stacking inter­actions [centroid–centroid distance = 3.4367 (6) Å].
doi:10.1107/S1600536810011931
PMCID: PMC2979246  PMID: 21579120
4.  1-[5-(Anthracen-9-yl)-3-(4-nitro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one 
In the title compound, C25H19N3O3, steric repulsion between the methine H atom and one of the anthryl H atoms seems to be concomitant with the considerable distortion of the anthryl fragment from planarity. The side rings of the anthryl subtend an angle of 9.57 (8)°, which is an extreme value among the known reliably determined structures. This angle correlates with the length of the bond by which the anthryl is attached to the rest of the mol­ecule. In the anthryl fragment, the maximum deviation of one of the C atoms from the mean plane is 0.126 (3) Å and regards the carrier C atom involved in the repulsion between the anthryl and the methine H atoms. The inter­planar angle between the pyrazoline ring and the anthryl fragment is 88.36 (5)° and that between the pyrazoline and 4-nitro­phenyl rings is 8.80 (15)°. Weak inter­molecular C—H⋯N, C—H⋯π and π–π inter­actions [centroid–centroid distances of 3.7659 (17), 3.9477 (15) and 3.8972 (15) Å] are pesent in the structure.
doi:10.1107/S1600536810053365
PMCID: PMC3051795  PMID: 21523061
5.  3-(4-Amino­phen­yl)-5-(4-meth­oxy­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide 
In the mol­ecule of title pyrazoline derivative, C17H18N4OS, the pyrazole ring adopts an envelope conformation with the flap atom, which bears the meth­oxy­phenyl substituent, displaced by 0.0750 (12) Å from the plane through the other ring atoms. The two substituted benzene rings make a dihedral angle of 70.59 (6)°. The meth­oxy group is twisted slightly with respect to the attached benzene ring [Cmeth­yl—O—C—C torsion angle = −8.84 (15)°]. An intra­molecular N—H⋯N hydrogen bond occurs. In the crystal, the pyrazoline mol­ecules are linked by N—H⋯O and N—H⋯S hydrogen bonds into zigzag layers parallel to the bc plane and stacked along the a axis by π–π inter­actions with centroid–centroid distances of 3.4690 (7) and 3.5792 (7) Å. C—H⋯π inter­actions are also present.
doi:10.1107/S1600536813018096
PMCID: PMC3793732  PMID: 24109319
6.  1-Acetyl-3-ferrocenyl-5-(2-nitro­phen­yl)-2-pyrazoline 
In the title compound, [Fe(C5H5)(C16H14N3O3)], the pyrazoline ring and the substituted cyclo­penta­dienyl ring are nearly coplanar, with a dihedral angle of 8.17 (2)°, while the nitro-substituted benzene ring is twisted out of the pyrazoline ring plane by 70.76 (1)°. The mol­ecules in the crystal structure are held together by three inter­molecular C—H⋯O hydrogen bonds. There is also an intra­molecular C—H⋯N hydrogen bond. The H atoms of the methyl group are disordered equally over two positions.
doi:10.1107/S1600536808004236
PMCID: PMC2960933  PMID: 21201984
7.  1-[3-(2-Nitro­phen­yl)-5-phenyl-2-pyrazolin-1-yl]ethanone 
The title compound, C17H15N3O3, was prepared from 1-(2-nitro­phen­yl)-3-phenyl­prop-2-en-1-one and hydrazine. The dihedral angle between the benzene and phenyl rings is 74.55 (2)°. The pyrazoline ring is in a slight envelope conformation with the C atom bonded to the phenyl ring forming the flap. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds connect mol­ecules into chains along [100].
doi:10.1107/S1600536810020611
PMCID: PMC3006741  PMID: 21587827
8.  N′-[(Z)-4-Methyl­benzyl­idene]-4-nitro­benzohydrazide monohydrate 
In the title compound, C15H13N3O3·H2O, the two benzene rings form a dihedral angle of 2.03 (2)°. In the crystal structure, adjacent hydrazide mol­ecules are linked into dimers by water mol­ecules; these dimers are then stacked along the b axis. Inter­molecular O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds and a π–π stacking inter­action between the nitro­benzene and tolyl rings with a centroid–centroid distance of 3.8208 (3) Å are observed. There is also a short O⋯N contact [2.6824 (7) Å].
doi:10.1107/S1600536808037008
PMCID: PMC2960119  PMID: 21581313
9.  3-Methyl-1-(3-nitro­phen­yl)-5-phenyl-4,5-dihydro-1H-pyrazole 
In the title compound, C16H15N3O2, the planar [maximum deviation 0.156 (2) Å] pyrazoline ring is nearly coplanar with the 3-nitro­phenyl group and is approximately perpendicular to the phenyl ring, making dihedral angles of 3.80 (8) and 80.58 (10)°, respectively. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.
doi:10.1107/S1600536809031390
PMCID: PMC2970115  PMID: 21577565
10.  Ethyl 7-methyl-2-phenyl­pyrazolo­[1,5-a]pyrimidine-5-carboxyl­ate 
The fused pyrazole and pyrimidine rings in the title compound, C16H15N3O2, are almost coplanar, being inclined to one another by 1.31 (12)°. The mean plane of this fused ring system is nearly coplanar with the phenyl ring, as indicated by the dihedral angle between their planes of 1.31 (12)°. The fused-ring system and the phenyl ring are nearly coplanar, as indicated by the dihedral angle of 1.27 (10)°. In the crystal, mol­ecules form inversion dimers via pairs of C—H⋯O hydrogen bonds. C—H⋯N inter­actions connect the dimers into a three-dimensional network. In addition, π–π contacts are observed, with centroid–centroid distances of 3.426 (2) Å.
doi:10.1107/S1600536813009902
PMCID: PMC3648271  PMID: 23723891
11.  (Z)-3-(9-Anthr­yl)-1-(4-bromo­phen­yl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one 
In the title mol­ecule, C26H16BrN3O3, the anthracene and benzene mean planes make dihedral angles of 63.79 (2) and 14.67 (2)°, respectively, with the plane of the imidazole ring. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules to form centrosymmetric dimers. Weak π–π stacking inter­actions, with centroid–centroid distances of 3.779 (2) and 3.826 (2) Å, supply additional stabilization. The crystal packing also exhibits short inter­molecular contacts between the nitro groups and Br atoms [Br⋯O = 3.114 (2) Å].
doi:10.1107/S1600536809018352
PMCID: PMC2969633  PMID: 21583241
12.  N-(2-Bromo-4-methyl­phen­yl)-2-(5-methyl-2-phenyl­pyrazolo­[1,5-a]pyrimidin-7-yl)acetamide 
The fused pyrazole and pyrimidine rings in the title compound, C22H19BrN4O, are almost coplanar, their planes being inclined to one another by 2.08 (13)°. The dihedral angles formed by the mean plane of the fused ring system and the phenyl and benzene rings are 16.21 (4) and 82.84 (4)°, respectively. An intra­molecular N—H⋯N hydrogen bond is observed. In the crystal, mol­ecules form inversion dimers via pairs of C—H⋯O hydrogen bonds. π–π inter­actions, with centroid–centroid distances of 3.4916 (9) Å, connect the dimers into a three-dimensional network.
doi:10.1107/S1600536813011811
PMCID: PMC3684917  PMID: 23795019
13.  1-[3-(2-Benz­yloxy-6-hy­droxy-4-methyl­phen­yl)-5-[3,5-bis­(tri­fluoro­meth­yl)phen­yl]-4,5-di­hydro-1H-pyrazol-1-yl]propane-1-one 
In the title compound, C28H24F6N2O3, the mean plane of the central pyrazoline ring forms dihedral angles of 2.08 (9) and 69.02 (16)° with the 2-benz­yloxy-6-hy­droxy-4-methyl­phenyl and 3,5-bis­(tri­fluoro­meth­yl)phenyl rings, respectively. The dihedral angle between the mean planes of the pyrazoline and 3,5-bis­(tri­fluoro­meth­yl)phenyl rings is 68.97 (9)°. An intra­molecular O—H⋯N hydrogen bond is observed, which forms an S(6) graph-set motif. In the crystal, pairs of weak C—H⋯F halogen inter­actions link the mol­ecules into inversion dimers while molecular chains along [100] are formed by C—H⋯O contacts.
doi:10.1107/S160053681301180X
PMCID: PMC3684926  PMID: 23795028
14.  (2E)-1-(2,4-Dichloro­phen­yl)-3-[3-(4-nitro­phen­yl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one 
In the title compound, C24H15Cl2N3O3, the C=C double bond is E configured. The 1-phenyl-1H-pyrazole moiety is roughly planar (r.m.s. deviation of all fitted non-H atoms = 0.0780 Å), but the mean planes of the two components are inclined at an angle of 9.95 (7)°. The mean plane defined by the non-H atoms of the 1H-pyrazole ring encloses angles of 9.95 (7), 24.54 (6) and 43.02 (6)° with the mean planes of the different benzene rings. In the crystal, C—H⋯O contacts are present and result in the formation of a double-layer two-dimensional network lying parallel to (110). The shortest inter­centroid distance between two aromatic systems is 3.5455 (7) Å and is apparent between two pyrazole systems. Further π–π inter­actions are manifest between a pair of 4-nitro­phenyl rings [centroid-to-centroid distance = 3.6443 (7) Å] and a pair of 2,4-dichloro­phenyl rings [centroid-to-centroid distance = 3.7797 (7) Å].
doi:10.1107/S1600536812003960
PMCID: PMC3295416  PMID: 22412527
15.  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
16.  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
17.  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
18.  [3-(5-Nitro-2-fur­yl)-1-phenyl-1H-pyrazol-4-yl](phen­yl)methanone 
In the title pyrazole compound, C20H13N3O4, an intra­molecular C—H⋯O hydrogen bond generates a seven-membered ring, producing an S(7) ring motif. The essentially planar furan and pyrazole rings [maximum deviations of 0.002 (1) and 0.007 (1) Å, respectively] are coplanar with each other, forming a dihedral angle of 3.06 (10)°. The pyrazole ring forms dihedral angles of 8.51 (9) and 56.81 (9)° with the two benzene rings. The nitro group is coplanar with the attached furan ring, as indicated by the dihedral angle of 2.5 (3)°. In the crystal packing, inter­molecular C—H⋯O hydrogen bonds link adjacent mol­ecules into two-mol­ecule-wide chains along the a axis. The crystal packing is further stabilized by weak inter­molecular C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.4441 (10) Å].
doi:10.1107/S1600536810015199
PMCID: PMC2979013  PMID: 21579253
19.  3-(4-Bromo­phen­yl)-3-(4-hydr­oxy-6-oxo-1,6-dihydro­pyrimidin-5-yl)-N-[(S)-1-phenyl­ethyl]propanamide 
In the mol­ecule of the title compound, C21H20BrN3O3, the pyrimidine ring is oriented at dihedral angles of 80.87 (3) and 15.99 (3)°, respectively, to the pyrimidine and bromo­phenyl rings. The dihedral angle between the two benzene rings is 88.37 (3)°. In the crystal structure, inter­molecular N—H⋯O and O—H⋯N hydrogen bonds link the mol­ecules. A π–π contact between pyrimidine and phenyl rings [centroid–centroid distance = 3.776 (3) Å] may further stabilize the structure. The methine H and the methyl C and H atoms are disordered over two positions and were refined with occupancies of 0.522 (13) and 0.478 (13).
doi:10.1107/S1600536809003821
PMCID: PMC2968538  PMID: 21582156
20.  2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-nitro­benzoate 
In the title compound, C13H12N4O6, the mean plane through the nitro­benzene forms a dihedral angle of 37.38 (15)° with the plane through the imidazole ring. The crystal packing is stabilized by weak inter­molecular C—H⋯O and C—H⋯N inter­actions together with π–π stacking inter­actions between nitro­benzene rings [centroid–centroid distance = 3.788 (3) Å] and between imidazole rings [centroid–centroid distance = 3.590 (2) Å].
doi:10.1107/S1600536810004186
PMCID: PMC2983685  PMID: 21580319
21.  2,4-Diiodo-3-nitro­anisole 
In the title compound (systematic name: 1,3-diiodo-4-meth­oxy-2-nitro­benzene), C7H5I2NO3, the dihedral angle between the benzene ring and the nitro group is 88.0 (3)°, and the methyl group lies almost in the same plane as the ring [deviation = 0.034 (6) Å]. In the crystal, aromatic π–π stacking occurs between inversion-related rings [centroid–centroid separation = 3.865 (3) Å and slippage = 0.642 Å]. A possible weak C—I⋯π inter­action occurs [I⋯π = 3.701 (2) Å and C—I⋯π = 130.18 (13)°], but there are no significant inter­molecular I⋯I contacts.
doi:10.1107/S160053681200952X
PMCID: PMC3344609  PMID: 22590371
22.  tert-Butyl N-{4-methyl-3-[4-(3-pyrid­yl)pyrimidin-2-yl­oxy]phen­yl}carbamate 
In the mol­ecule of the title compound, C21H22N4O3, the pyrimidine ring is oriented at dihedral angles of 0.51 (3) and 50.76 (3)° to the pyridine and benzene rings, respectively. In the crystal structure, inter­molecular N—H⋯N hydrogen bonds link the mol­ecules into centrosymmetric dimers, forming R 2 2(24) ring motifs; the dimers are linked by inter­molecular C—H⋯O hydrogen bonds into a two-dimensional network. π–π contacts between the benzene rings and between the pyrimidine and pyridine rings [centroid–centroid distances = 3.891 (1) and 3.646 (1) Å, respectively] may further stabilize the structure. Two weak C—H⋯π inter­actions are also present.
doi:10.1107/S1600536809025604
PMCID: PMC2977178  PMID: 21583549
23.  1-[(Bromo­meth­yl)(phen­yl)meth­ylene]-2-(2,4-dinitro­phen­yl)hydrazine 
The title compound, C14H11BrN4O4, comprises two crystallographically independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule B, intra­molecular bifurcated N—H⋯O and N—H⋯Br hydrogen bonds and in mol­ecule A, an intra­molecular N—H⋯O hydrogen bond generate S(6) ring motifs. The dihedral angle between the phenyl and benzene rings is 5.44 (6) in mol­ecule A and 7.63 (6)° in mol­ecule B. The ortho- and meta-nitro substituents make dihedral angles of 6.67 (15) and 2.26 (15)° to the attached benzene ring in mol­ecule A and 6.37 (17) and 5.81 (16)° in mol­ecule B. The Br atom in mol­ecule B is disordered over two positions with a refined site-occupancy ratio of 0.61 (3):0.39 (3). Inter­esting features of the crystal structure are the short Br⋯N [3.257 (3)–3.294 (4) Å], Br⋯O [3.279 (3)–3.307 (4) Å] and O⋯O [2.9319 (16)–2.9995 (16) Å] contacts, which are shorter than the sum of the van der Waals radii of these atoms. The crystal structure is further stabilized by inter­molecular C—H⋯O and π–π inter­actions [centroid–centroid distances = 3.6643 (8)–3.8514 (8) Å].
doi:10.1107/S1600536809016225
PMCID: PMC2969738  PMID: 21583090
24.  1-[3-(4-Fluoro­phen­yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title compound, C17H15FN2O, the pyrazoline ring adopts a flattened envelope conformation. The dihedral angle between the fluoro-substituted benzene ring and the phenyl ring is 69.20 (5)°. In the crystal, a pair of C—H⋯O hydrogen bonds link neighbouring mol­ecules, forming an inversion dimer. The crystal structure is further consolidated by C—H⋯π inter­actions and by a π–π inter­action with a centroid–centroid distance of 3.7379 (6) Å.
doi:10.1107/S1600536812033971
PMCID: PMC3435661  PMID: 22969534
25.  1-[3-(Anthracen-9-yl)-5-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title compound, C24H19N3O, the pyrazoline ring adopts an envelope conformation with the C atom linking to the pyridine ring as the flap. The mean plane of the pyrazoline ring makes dihedral angles of 85.54 (4) and 81.66 (3)° with the pyridine ring and the anthracene ring system, respectively. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds. In addition, weak π–π inter­actions [centroid–centroid distances = 3.695 (3)–3.850 (7) Å] are observed.
doi:10.1107/S160053681201505X
PMCID: PMC3344501  PMID: 22590263

Results 1-25 (129183)