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1.  6-(4-Amino­phen­yl)-2-meth­oxy-4-phenyl­nicotino­nitrile 
In the structure of the title nicotino­nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino­phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π–π inter­actions between the 4-amino­phenyl rings of adjacent sheets, with centroid–centroid distances of 3.7499 (9) Å. C—H⋯π inter­actions are also present.
doi:10.1107/S1600536813031437
PMCID: PMC3885069  PMID: 24454245
2.  6-Meth­oxy-4-(2,4,5-tri­meth­oxy­phen­yl)-2,2′-bi­pyridine-5-carbo­nitrile 
In the title 3-cyano­pyridine derivative, C21H19N3O4, the 3-cyano-substituted pyridine ring forms dihedral angles of 2.35 (5) and 41.60 (5)° with the unsubstituted pyridine and 2,4,5-trimeth­oxy-substituted benzene rings, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. The meth­oxy groups form Cmeth­yl—O—C—(C,N) torsion angles in the range 0.80 (15)–11.45 (15)°. In the crystal, mol­ecules related by 21 screw axes are linked by weak C—H⋯N hydrogen bonds along [010]. In addition, weak C—H⋯π inter­actions and π–π stacking inter­actions between pyridine rings, with a centroid–centroid distance of 3.6448 (6) Å, are observed.
doi:10.1107/S1600536813023891
PMCID: PMC3790375  PMID: 24098197
3.  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
4.  (2E)-1-(Pyridin-2-yl)-3-(2,4,5-tri­meth­oxy­phen­yl)prop-2-en-1-one 
The title heteroaryl chalcone derivative, C17H17NO4, is close to planar: the dihedral angle between the pyridine and benzene rings is 3.71 (11)° and the meth­oxy C atoms deviate from their attached ring by 0.046 (3), −0.044 (2) and 0.127 (3) Å. The disposition of the pyridine N atom and the carbonyl group is anti [N—C—C—O = −177.7 (2)°]. In the crystal, mol­ecules are linked by weak C—H⋯N and C—H⋯O inter­actions into (100) sheets and an aromatic π–π stacking inter­action between the pyridine and benzene ring, with a centroid–centroid separation of 3.7036 (14) Å also occurs.
doi:10.1107/S1600536813015821
PMCID: PMC3770358  PMID: 24046643
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.  6-(4-Amino­phen­yl)-4-(4-eth­oxy­phen­yl)-2-meth­oxy­nicotinonitrile 
In the title mol­ecule, C21H19N3O2, the central pyridine ring makes dihedral angles of 14.46 (9) and 34.67 (8)° with the 4-amino- and 4-eth­oxy-substituted benzene rings, respectively. The eth­oxy group is essentially coplanar with the attached benzene ring [C—O—C—C torsion angle = 178.70 (16)°] as is the meth­oxy group with the pyridine ring [C—O—C—N torsion angle = −3.0 (3)°]. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds into chains along [201]. Weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions are also present.
doi:10.1107/S1600536812036276
PMCID: PMC3435837  PMID: 22969683
7.  5-Amino-3-eth­oxy-1,8,8-trimethyl-2-aza­bicyclo­[2.2.2]octa-2,5-diene-4,6-dicarbo­nitrile 
The title 2-aza­bicyclo­[2.2.2]octa-2,5-diene derivative, C14H18N4O, crystallized out with two independent mol­ecules with similar conformations in the asymmetric unit. In each mol­ecule, the three six-membered rings adopt boat conformations. The mol­ecules exist in the enamine form. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯N hydrogen bonds into a two-dimensional network parallel to the ab plane.
doi:10.1107/S1600536812032990
PMCID: PMC3435638  PMID: 22969511
8.  5-(4-Eth­oxy­phen­yl)-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C17H18N4OS, a pyrazoline derivative, the pyrazoline ring adopts an envelope conformation with the C atom bonded to the benzene ring as the flap atom. The dihedral angle between the pyridine and benzene rings is 80.50 (6)°. The eth­oxy­phenyl group is approximately planar, with an r.m.s. deviation of 0.0238 (1) Å for the nine non-H atoms. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯S hydrogen bonds into a tape along the b axis. Weak C—H⋯N and C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812006642
PMCID: PMC3297890  PMID: 22412693
9.  (E)-1-(Furan-2-yl)-3-(2,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the title chalcone derivative, C16H16O5, the dihedral angle between the furan and benzene rings is 2.06 (17)°. The two meth­oxy groups at the ortho and para positions are essentially coplanar with the benzene ring [C—O—C—C angles = −1.0 (5) and 178.5 (3)°], whereas the third one at the meta position is slightly twisted [C—O—C—C = 9.6 (5)°]. In the crystal, weak C—H⋯O inter­actions link the mol­ecules into a sheet parallel to (02). An inter­molecular π–π inter­action between the furan and benzene rings is present [centroid–centroid distance = 3.772 (2) Å]. A short C⋯C contact [3.173 (5) Å] is also observed between neighbouring furan rings.
doi:10.1107/S1600536812000037
PMCID: PMC3275007  PMID: 22346952
10.  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
11.  5-(4-Meth­oxy­phen­yl)-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C16H16N4OS, the dihedral angle between the pyridine and benzene rings is 81.08 (6)°. The pyrazole ring makes dihedral angles of 12.36 (7) and 87.96 (6)°, respectively, with the pyridine and benzene rings. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯S hydrogen bonds and a weak C—H⋯S inter­action into a layer parallel to the ab plane. Weak C—H⋯π and π–π inter­actions [centroid–centroid distances = 3.7043 (9) and 3.8120 (7) Å] are also observed.
doi:10.1107/S1600536811050033
PMCID: PMC3239124  PMID: 22199972
12.  1,5-Bis(thio­phen-2-yl)-3-(2,4,5-trimeth­oxy­phen­yl)pentane-1,5-dione 
In the title 1,5-diketone compound, C22H22O5S2, the benzene ring makes dihedral angles of 41.51 (6) and 25.83 (6)° with the two thio­phene rings, while the dihedral angle between the thio­phene rings is 26.67 (7)°. An intra­molecular C—H⋯O inter­action generates an S(9) ring motif. In the crystal, mol­ecules are linked into a three-dimensional network by weak C—H⋯O and C—H⋯π inter­actions, and a π–π inter­action with a centroid–centroid distance of 3.6527 (8) Å.
doi:10.1107/S160053681104846X
PMCID: PMC3239053  PMID: 22199901
13.  (E)-1-(Thio­phen-2-yl)-3-(2,4,6-tri­meth­oxy­phen­yl)prop-2-en-1-one 
There are two crystallograpically independent mol­ecules in the asymmetric unit of the title heteroaryl chalcone derivative, C16H16O4S, with slightly different conformations. The thienyl ring of one mol­ecule is disordered over two positions, with a refined site-occupancy ratio of 0.713 (5):0.287 (5). The mol­ecules are twisted: the dihedral angle between the thienyl and benzene rings is 9.72 (19)° in the ordered mol­ecule, and 3.8 (4) and 2.1 (8)° for the major and minor components, respectively, in the disordered mol­ecule. In both mol­ecules, all three substituted meth­oxy groups are coplanar with the benzene ring to which they are attached. In each mol­ecule, a weak intra­molecular C—H⋯O inter­action generates an S(6) ring motif. In the crystal structure, adjacent mol­ecules are linked into a three-dimensional network by weak C—H⋯O inter­actions.
doi:10.1107/S1600536811042930
PMCID: PMC3247464  PMID: 22220082
14.  (2E)-1-(Pyridin-2-yl)-3-(2,4,6-trimeth­oxy­phen­yl)prop-2-en-1-one 
The title heteroaryl chalcone derivative, C17H17NO4, is a condensation product of 2-acetyl­pyridine and 2,4,6-trimeth­oxy­benzaldehyde. The mol­ecule is roughly planar, the dihedral angle between the pyridine and benzene rings being 5.51 (10)°. All the three meth­oxy groups are almost co-planar with the bound benzene ring [r.m.s. deviation of 0.0306 (2) Å]. A weak C—H⋯O intra­molecular inter­action involving one of the ortho-meth­oxy groups generates an S(6) ring motif. In the crystal, the mol­ecules are linked by weak C—H⋯O inter­actions into anti-parallel face-to-face pairs. Adjacent pairs are further connected into sheets parallel to the ab plane.
doi:10.1107/S1600536811039110
PMCID: PMC3201482  PMID: 22065835
15.  (E)-1-(Pyridin-2-yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the title heteroaryl chalcone derivative, C17H17NO4, the dihedral angle between the pyridine and benzene rings is 10.82 (5)°. The two meth­oxy groups at the meta positions are essentially coplanar with the attached benzene rings [C—O—C—C torsion angles = −0.97 (14) and 179.47 (9)°], whereas the meth­oxy group at the para position is twisted from the attached ring with a C—O—C—C torsion angle of −104.48 (11)°. A C—H⋯O close contact involving two of the meth­oxy groups generates an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions into columns along the b axis.
doi:10.1107/S1600536811033198
PMCID: PMC3200663  PMID: 22058997
16.  (E)-1-(2-Hy­droxy­phen­yl)-3-(2,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the title chalcone derivative, C18H18O5, the dihedral angle between the hy­droxy-substituted benzene ring and the trimeth­oxy-substituted benzene ring is 16.3 (1)°. The three meth­oxy groups are essentially coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0208 Å. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, weak C—H⋯O inter­actions link mol­ecules into helical chains along the b axis. These chains are connected into sheets parallel to the bc plane by further weak C—H⋯O inter­actions.
doi:10.1107/S1600536811031382
PMCID: PMC3200911  PMID: 22058930
17.  3-(4-Bromo­phen­yl)-5-[4-(dimethyl­amino)­phen­yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
The mol­ecule of the title pyrazole derivative, C18H19BrN4S, is twisted. The central pyrazole ring, which adopts a flattened envelope conformation, is almost coplanar with the 4-bromo­phenyl ring, whereas it is inclined to the 4-(dimethyl­amino)­phenyl ring making dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two benzene rings is 86.56 (6)°. The dimethyl­amino group is slightly twisted from the attached benzene ring [C—C—N—C torsion angles = 8.4 (2) and 8.9 (2)°]. In the crystal, mol­ecules are linked by inter­molecular N—H⋯S hydrogen bonds into chains along [20]. The crystal is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811006106
PMCID: PMC3052174  PMID: 21522446
18.  (E)-1-(2-Fur­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
The title mol­ecule, C16H16O5, is twisted; the dihedral angle between the furan and 3,4,5-trimeth­oxy­phenyl rings is 12.14 (13)°. The two meth­oxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C—O—C—C = −0.6 (3) and 1.4 (3)°], whereas the third meth­oxy group, at the para position, is (+)-anti­clinal with respect to the benzene ring [C—O—C—C = 104.9 (2)°]. In the crystal, mol­ecules are linked by weak C—H⋯O bonds to stack along the b axis and further C—H⋯O inter­actions consolidate the structure.
doi:10.1107/S160053681004451X
PMCID: PMC3011481  PMID: 21589380
19.  (E)-1-(2-Fur­yl)-3-(2,4,6-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the title heteroaryl chalcone derivative, C16H16O5, the dihedral angle between the furan and benzene rings is 14.45 (6)°. The three meth­oxy groups are almost coplanar with their attached benzene ring [C—C—O—C torsion angles = 2.07 (17), −5.04 (17) and 2.85 (16)°]. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, adjacent mol­ecules are linked into X-shaped chains along the c axis by weak C—H⋯O(enone) inter­actions. These chains are stacked along the b axis. C⋯O [3.3308 (13)–3.4123 (14) Å] short contacts are also observed.
doi:10.1107/S1600536810035762
PMCID: PMC2983191  PMID: 21587546
20.  (E)-3-(Anthracen-9-yl)-1-(furan-2-yl)prop-2-en-1-one1  
In the mol­ecule of the title heteroaryl chalcone derivative, C21H14O2, the almost planar prop-2-en-1-one unit [r.m.s. deviation = 0.0087 (1) Å] forms dihedral angles of 5.81 (7) and 49.85 (6)°, respectively, with the furan ring and anthracene ring system. In the crystal structure, the mol­ecules are linked into a two-dimensional network parallel to (100) by C—H⋯O hydrogen bonds and π⋯π inter­actions involving the furan rings [centroid–centroid distance = 3.7205 (6) Å].
doi:10.1107/S1600536810005982
PMCID: PMC2983903  PMID: 21580637
21.  6-(4-Bromo­phen­yl)-2-eth­oxy-4-(2,4,5-trimethoxy­phen­yl)nicotinonitrile1  
There are two mol­ecules in the asymmetric unit of the title compound, C23H21BrN2O4, which differ in the conformation of their ethoxy residues, i.e. almost co-planar with the pyridine ring in one mol­ecule [C—O—C—C = −174.0 (2)°] but almost perpendicular in the other [C—O—C—C = 92.8 (3)°]. The dihedral angles between the central pyridine ring and the 4-bromo­phenyl and 2,4,5-trimethoxy­phenyl rings are 11.05 (12) and 63.78 (12)°, respectively, in one mol­ecule; the corres­ponding angles in the other mol­ecule are 30.38 (13) and 65.38 (13)°, respectively. In the crystal structure, pairs of mol­ecules are arranged in a face-to-face sandwich structure which further stacks along the b axis. The crystal packing features C—H⋯π inter­actions and Br⋯O [3.5417 (17) Å], Br⋯C [3.748 (3) Å], C⋯N [3.376 (4) Å] and C⋯O [3.351 (3)–3.409 (3) Å] contacts. Finally, π⋯π inter­actions [centroid⋯centroid distances = 3.6346 (19) and 3.6882 (19) Å] are observed.
doi:10.1107/S1600536810005210
PMCID: PMC2983629  PMID: 21580396
22.  A second ortho­rhom­bic polymorph of (Z)-3-(9-anthr­yl)-1-(2-thien­yl)prop-2-en-1-one1  
The title heteroaryl chalcone, C21H14OS, is a second ortho­rhom­bic polymorph which crystallizes in the space group P212121. The structure was previously reported [Fun et al. (2009 ▶). Acta Cryst. E65, o2168-o2169] in the space group Pna21. The bond distances and angles are similar in both structures. In contrast, the overall crystal packing is different from that in the first ortho­rhom­bic Pna21 polymorph in which mol­ecules were stacked into columns along the b axis and the thio­phene units of two adjacent columns were stacked in a head to tail fashion. In the present polymorph, mol­ecules are found to dimerize through a weak S⋯S inter­action [3.6513 (7) Å] and these dimers are arranged into sheets parallel to the bc plane. There are no classical hydrogen bonds in the packing which features short C⋯O [3.2832 (2)–3.6251 (9) Å], C⋯S [3.4879 (17)–3.6251 (19) Å] and S⋯O [2.9948 (16) Å] contacts, together with C—H⋯π inter­actions. Similar contacts were found in the other polymorph.
doi:10.1107/S1600536810000061
PMCID: PMC2979950  PMID: 21579743
23.  6-(4-Bromo­phen­yl)-2-eth­oxy-4-(4-ethoxy­phen­yl)nicotinonitrile 
The mol­ecule of the title nicotinonitrile derivative, C22H19BrN2O2, is non-planar, the central pyridine ring making dihedral angles of 7.34 (14) and 43.56 (15)° with the 4-bromo­phenyl and 4-ethoxy­phenyl rings, respectively. The eth­oxy group of the 4-ethoxy­phenyl is slightly twisted from the attached benzene ring [C—O—C—C = 174.2 (3)°], whereas the eth­oxy group attached to the pyridine ring is in a (+)syn-clinal conformation [C—O—C—C = 83.0 (3)°]. A weak intra­molecular C—H⋯N inter­action generates an S(5) ring motif. In the crystal structure, the mol­ecules are linked by weak inter­molecular C—H⋯N inter­actions into screw chains along the b axis. These chains stacked along the a axis. π–π inter­actions with centroid–centroid distances of 3.8724 (16) and 3.8727 (16) Å are also observed.
doi:10.1107/S1600536809051861
PMCID: PMC2980143  PMID: 21580178
24.  6-(4-Bromo­phen­yl)-2-eth­oxy-4-(2,4,6-trimethoxy­phen­yl)nicotinonitrile1  
In the asymmetric unit of the title nicotinonitrile derivative, C23H21BrN2O4, there are two non-planar independent mol­ecules. The central pyridine ring makes dihedral angles of 9.05 (7) and 77.06 (7)°, respectively, with the 4-bromo­phenyl and 2,4,6-trimethoxy­phenyl rings in one mol­ecule, whereas the corresponding values are 5.96 (7) and 82.37 (7)° in the other. All the three meth­oxy groups are essentially in the plane of the attached benzene ring [C—O—C—C angles = 2.99 (19), 4.8 (2) and −6.2 (2)° in one mol­ecule, and 2.69 (18), 176.73 (15) and 1.3 (2)° in the other]. The eth­oxy group is slightly twisted in one mol­ecule [C—C—O—C = 173.84 (12)°], whereas it is coplanar with the pyridine ring in the other [C—C—O—C = −177.23 (13)°]. Weak intra­molecular C—H⋯N inter­actions generate S(5) ring motifs. In the crystal structure, the mol­ecules are linked by weak inter­molecular C—H⋯N and C—H⋯O inter­actions into a supra­molecular three-dimensional network in such a way that the nicotinonitrile units of neighboring mol­ecules are stacked in an anti­parallel manner along the c axis. The crystal is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536809043943
PMCID: PMC2971038  PMID: 21578493
25.  (Z)-3-(9-Anthr­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one1  
The title chalcone derivative, C24H18O2, which consists of the substituted 4-methoxy­phenyl and anthracene rings bridged by the prop-2-en-1-one unit, exists in a cis configuration. The mol­ecule is twisted, the inter­planar angle between the benzene and anthracene rings being 69.50 (10)°. The meth­oxy group is coplanar with the attached benzene ring [C—O—C—C angle = 2.9 (3)°]. In the crystal structure, mol­ecules are linked into chains along the a axis by a weak C—H⋯O(enone) inter­action. The chains are stacked along the c axis. A C—H⋯π inter­action involving the benzene ring is observed.
doi:10.1107/S1600536809038665
PMCID: PMC2971453  PMID: 21578282

Results 1-25 (31)