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1.  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].
PMCID: PMC3009369  PMID: 21588948
2.  2-[6-(4-Chloro­phen­yl)imidazo[2,1-b][1,3]thia­zol-2-yl]-N′-[(E)-4-meth­oxy­benzyl­idene]acetohydrazide 
In the imidazo[2,1-b][1,3]thia­zole group of the title compound, C21H17ClN4O2S, the dihedral angle between the thia­zole and imidazole rings is 1.9 (2)°. The mean plane of this group makes dihedral angles of 5.5 (2) and 39.9 (2)° with the benzene rings of the chloro­phenyl and meth­oxy­phenyl groups, respectively. The dihedral angle between these two benzene rings is 34.4 (2)°. In the crystal, mol­ecules are connected to each other by inter­molecular N—H⋯O hydrogen bonds along the b axis, generating a C(4) chain. Weak C—H⋯π inter­actions also occur.
PMCID: PMC3050215  PMID: 21522689
3.  3-{[6-(4-Chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazol-2-yl]meth­yl}-1,2-benzoxazole 
In the title compound, C18H11ClN4OS, the benzisoxazole and imidazothia­diazole rings are inclined at an angle of 23.81 (7)° with respect to each other. The imidazothia­diazole and chloro­phenyl rings make a dihedral angle of 27.34 (3)°. In the crystal, inter­molecular C—H⋯N inter­actions generate a chain along the c axis and C—H⋯O inter­actions form centrosymmetric dimers resulting in an R 2 2(26) graph-set motif. Moreover, the C—H⋯N and S⋯N [3.206 (4) Å] inter­actions links the mol­ecules into R(7) ring motifs. The packing is further stabilized by π–π stacking inter­actions between the thia­diazole rings with a shortest centroid–centroid distance of 3.497 (3) Å. In addition, C—H⋯π inter­actions are observed in the crystal structure
PMCID: PMC3052169  PMID: 21522374
4.  6-(4-Chloro­phen­yl)-3-methyl­imidazo[2,1-b]thia­zole 
In the title compound, C12H9ClN2S, the imidazo[2,1-b]thia­zole fragment is planar (r.m.s. deviation = 0.003 Å), and the benzene ring is twisted slightly [by 5.65 (6)°] relative to this moiety. In the crystal, mol­ecules are linked by π–π stacking inter­actions into columns along [010]. The mol­ecules within the columns are arranged alternatively by their planar rotation of 180°. Thus, in the columns, there are the two types of π–π stacking inter­actions, namely, (i) between two imidazo[2,1-b]thia­zole fragments [inter­planar distance = 3.351 (2) Å] and (ii) between an imidazo[2,1-b]thia­zole fragment and the phenyl ring [inter­planar distance = 3.410 (5) Å]. There are no short contacts between the columns.
PMCID: PMC3884351  PMID: 24454127
5.  Ethyl 2-[1-(4-chloro­phen­yl)-2,5-dioxo-1,2,3,5-tetra­hydro­imidazo[1′,2′:1,2]pyrimidino[5,4-b][1]benzofuran-3-yl]acetate 
The asymmetric unit of the title compound, C22H16ClN3O5, consists of two crystallographically independent mol­ecules. The fused rings of the imidazo[1,2-a]benzo[4,5]furo[3,2-d]pyrimidine system are nearly coplanar and the chlorophenyl rings are twisted with respect to the two pyrimidinone ring systems by 71.00 (2) and 62.59 (2)°. The C atoms of the ethyl side chain are disordered and were refined using a split model. In the crystal structure, the mol­ecules are connected via weak intra- and inter­molecular C—H⋯O inter­actions are present. The ethyl group in one molecule is disordered over two positions, with site occupancy factors 0.55 and 0.45; in the other molecule only the methyl group is disordered over two positions, with site occupancy factors 0.6 and 0.4.
PMCID: PMC2915365  PMID: 21200883
6.  6-(4-Chloro­phen­yl)-2-isobutyl­imidazo[2,1-b][1,3,4]thia­diazole 
In the title compound, C14H14ClN3S, the imidazo[2,1-b][1,3,4]thia­diazole system is essentially planar, with a maximum deviation of 0.006 (2) Å. The dihedral angle between the imidazo[2,1-b][1,3,4]thia­diazole and chloro­phenyl rings is 5.07 (8)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak π–π [centroid–centroid distance = 3.5697 (11) Å] and C—H⋯π inter­actions.
PMCID: PMC3050343  PMID: 21522707
7.  1-(6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)-3-(2-chloro­phen­yl)urea 
In the title compound, C14H11Cl2N5O, the plane of the 1H-imidazo[4,5-c]pyridine ring system [r.m.s. deviation = 0.087 (19) Å] makes a dihedral angle of 4.87 (10)° with the terminal phenyl ring. An intra­molecular N—H⋯N hydrogen bond stabilizes the mol­ecular conformation. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into inversion dimers. These dimers are connected by π–π inter­actions between imidazole rings [shortest centroid–centroid distance = 3.4443 (14) Å].
PMCID: PMC3998316  PMID: 24764877
8.  1-Methyl-3-(4-chloro­benzo­yl)imidazo[1,2-a]pyridin-1-ium-2-olate 
In the mol­ecule of the title compound, C15H11ClN2O2, the nine-membered heterobicycle is approximately planar [largest deviation from least-squares plane = 0.012 (2) Å] and forms a dihedral angle of 51.14 (8)° with the plane of the 4-chloro­phenyl group. There is a non-classical intra­molecular hydrogen bond between the pyridine α-H atom and the O atom of the benzoyl group. The crystal structure is stabilized by weak C—H⋯O and C—H⋯Cl inter­actions involving the ‘olate’ O atom and the Cl atom attached to the benzoyl group as acceptors.
PMCID: PMC3201236  PMID: 22064572
9.  Crystal structures of methyl 3-phenyl-4,5-di­hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl­ate and methyl 1-methyl-3-phenyl-4,5-di­hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl­ate 
In two benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl­ates, the seven-membered oxazepane rings both have a twist-chair conformation. The dihedral angle between the phenyl ring and the benzimidazole ring system is significantly smaller in one of the compounds, viz. 73.42 (10) compared to 83.07 (17)°.
The title compounds, C19H18N2O3, (I), and C20H20N2O3, (II), differ only by a methyl substituent on the seven-membered oxazepine ring in (II). In both compounds, these rings have a twist-chair conformation. The phenyl ring makes a dihedral angle of 73.42 (10)° with the benzimidazole ring system mean plane (r.m.s. deviation = 0.015 Å) in (I) and 83.07 (7)° in (II) (r.m.s. deviation = 0.026 Å). The methyl carboxyl­ate groups are planar to within 0.031 (2) in (I) and 0.003 (2) Å in (II). They are inclined to the phenyl and benzimidazole ring system by 33.78 (16) and 87.56 (14)°, respectively, in (I) and by 53.04 (12) and 60.22 (11)°, respectively, in (II). In the crystal of (I), mol­ecules stack in a herringbone fashion and are linked by C—H⋯O hydrogen bonds, forming chains along [100]. In the crystal of (II), there are no significant inter­molecular inter­actions present.
PMCID: PMC4257324  PMID: 25484732
crystal structure; oxazepine; benzimidazole; angiogenesis; natural products.
10.  1′-(2-Chloro­phen­yl)-5,6,5′,6′,7′,7a′-hexa­hydro-1′H,1′′H-dispiro­[imidazo[2,1-b][1,3]thia­zole-2,2′-pyrrolizine-3′(2′H),3′′-indole]-2′′,3(2H,3′′H)-dione 
In the title compound, C24H21ClN4O2S, the two adjacent spiro junctions link an almost planar (r.m.s. deviation = 0.017 Å) 2-oxindole ring, a hexa­hydro-1H-pyrrolizine ring and a tetra­hydro­imidazo[2,1-b]thia­zole ring. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds occur, generating an R 2 2(16) loop.
PMCID: PMC2983913  PMID: 21580676
11.  Dichloridobis[3-(4-chloro­phen­yl)-2,N,N-trimethyl-2,3-di­hydro-1,2,4-oxa­diazole-5-amine-κN 4]platinum(II)–4-chloro­benzaldehyde (1/1) 
In the title 1:1 co-crystal, [PtCl2(C11H14ClN3O)2]·C7H5ClO, the coordination polyhedron of the PtII atom is slightly distorted square-planar with the chloride and 2,3-di­hydro-1,2,4-oxa­diazole ligands mutually trans, as the Pt atom lies on an inversion center. The 4-chloro­benzaldehyde mol­ecules are statistically disordered about an inversion centre with equal occupancies for the two positions. The PtII complex forms a three-dimensional structure through C—H⋯Cl and weaker C—H⋯O inter­actions with the 4-chloro­benzaldehyde mol­ecule.
PMCID: PMC3793686  PMID: 24109273
12.  6-(3-Chloro­phen­yl)imidazo[2,1-b][1,3,4]thia­diazole 
In the title compound, C10H8ClN3S, the dihedral angle between the mean planes of the benzene and imidazo[2,1-b][1,3,4]thia­diazole rings is 6.0 (9)°. In the crystal, mol­ecules are assembled by the formation of centrosymmetric dimers by π-stacking of the thia­diazole and benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.6938 (11) Å] along [010].
PMCID: PMC3588322  PMID: 23476447
13.  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.
PMCID: PMC3247609  PMID: 22219914
14.  2-(4-Chloro­phen­yl)imidazo[1,2-a]pyridine-3-carbaldehyde 
The asymmetric unit of the title compound, C14H9ClN2O, contains two mol­ecules with dihedral angles of 33.52 (11) and 34.58 (11)° between their benzene rings and imidazole ring systems. In the crystal, C—H⋯N and C—H⋯O inter­actions are observed. The crystal examined was found to be a racemic twin.
PMCID: PMC2971907  PMID: 21578903
15.  1-Isobutyl-4-meth­oxy-1H-imidazo[4,5-c]quinoline 
In the title compound, C15H17N3O, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.036 (1) Å. The C—N—C—C torsion angles formed between this ring system and the isobutyl unit are −99.77 (16) and 79.71 (17)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis.
PMCID: PMC3200859  PMID: 22058955
16.  N-tert-Butyl-2-(2,6-di­chloro­phen­yl)imidazo[1,2-a]pyrazin-3-amine 
In the title compound, C16H16Cl2N4, the imidazole ring mean plane makes a dihedral angle of 70.01 (1)° with the phenyl ring. The Cl atoms deviate by −0.0472 (6) and 0.0245 (8) Å from the plane of their attached benzene ring. In the crystal, mol­ecules are linked via pairs of C—H⋯N hydrogen bonds, forming inversion dimers.
PMCID: PMC3685091  PMID: 23795110
17.  Crystal structure of 5-amino-5′-chloro-6-(4-chloro­benzo­yl)-8-nitro-2,3-di­hydro-1H-spiro­[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one including an unknown solvent mol­ecule 
The asymmetric unit of the title compound, C21H15Cl2N5O4, contains two independent mol­ecules (A and B) having similar conformations. The amine (NH2) group forms an intra­molecular hydrogen bond with the benzoyl group, giving an S(6) ring motif in both mol­ecules. The central six-membered rings adopt sofa conformations and the imidazole rings are planar (r.m.s deviations = 0.0150 and 0.0166 Å). The pyridine and imidazole rings are inclined to one another by 3.54 (1) and 3.03 (1)° in mol­ecules A and B, respectively. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming chains along the a axis which enclose R 2 2(16) ring motifs. The rings are linked by weak N—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π inter­actions forming sheets lying parallel to (001). A region of disordered electron density, most probably disordered solvent mol­ecules, occupying voids of ca 753 Å3 for an electron count of 260, was treated using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.
PMCID: PMC4186207  PMID: 25309286
crystal structure; spiro; imidazole; pyridine-indoline C—H⋯π inter­actions; hydrogen bonding
18.  7-Chloro-4-[(E)-2-(4-methoxy­benzyl­idene)hydrazin-1-yl]quinoline monohydrate 
The organic mol­ecule in the title hydrate, C17H14ClN3O·H2O, has a small but significant twist from planarity, as seen in the dihedral angle of 12.10 (17)° between the quinoline and benzene rings. The conformation about the C=N bond is E. Chains along the b axis are formed in the crystal structure aided by water–quinoline O—H⋯N (× 2) and hydrazone–water N—H⋯O hydrogen bonds. Layers of these chains stack along the a axis via C—H⋯π and π–π inter­actions [ring centroid–ring centroid distance = 3.674 (2) Å]. C—H⋯O inter­actions are also present.
PMCID: PMC2983656  PMID: 21580437
19.  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.
PMCID: PMC3515270  PMID: 23284490
20.  2-(4-Fluoro­phen­yl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline monohydrate 
In the title compound, C25H15FN4·H2O, the fused ring system is essentially planar [maximum deviation of 0.0822 (14) Å]. The imidazole ring makes dihedral angles of 76.83 (7) and 32.22 (7)° with the phenyl group attached to nitro­gen and the fluoro­benzene group to carbon, respectively. The dihedral angle between the two phenyl rings is 72.13 (7)°. Inter­molecular O—H⋯N, O—H⋯F, C—H⋯F, C—H⋯O and C—H⋯N hydrogen bonds are found in the crystal structure.
PMCID: PMC3212347  PMID: 22091004
21.  (2-Chloro­phen­yl)(diphenyl­phosphor­yl)methanol 
The title compound, C19H16ClO2P, was obtained by the reaction of diphenyl­phosphine oxide with 2-chloro­benzaldehyde. The mol­ecule has a tetra­hedral structure at the P atom. The dihedral angle between the phenyl rings attached to the P atom is 80.4 (1)°. The mol­ecules are linked together by inter­molecular O—H⋯O and C—H⋯O hydrogen-bonding inter­actrions. The crystal studied was an inversion twin.
PMCID: PMC2915293  PMID: 21200800
22.  N-(4-Chloro­phen­yl)-2-(8-quinol­yloxy)acetamide monohydrate 
In the title compound, C17H13ClN2O2·H2O, the dihedral angle between the quinoline ring system and the benzene ring is 13.0 (1)°. An intra­molecular N—H⋯O hydrogen bond may influence the mol­ecular conformation. In the crystal structure, acetamide mol­ecules are linked to water mol­ecules via inter­molecular O—H⋯ N and N—H⋯O hydrogen bonds and in turn linked into chains along [010] via O—H⋯O hydrogen bonds.
PMCID: PMC3007349  PMID: 21588294
23.  Decacarbonyl-1κ3 C,2κ3 C,3κ4 C-bis­[tris­(3-chloro­phen­yl)phosphine]-1κP,2κP-triangulo-triruthenium(0) monohydrate 
The asymmetric unit of the title triangulo-triruthenium compound, [Ru3(C18H12Cl3P)2(CO)10]·H2O, consists of one triangulo-triruthenium complex and one disordered water solvent molecule. Two of the 3-chloro­phenyl rings are disordered over two positions with refined site occupancies of 0.671 (3)/0.329 (3) and 0.628 (3)/0.372 (3). The water mol­ecule is disordered over two positions with refined site occupancies of 0.523 (7) and 0.477 (7). Two equatorial carbonyl groups have been substituted by the two monodentate phosphine ligands, leaving one equatorial and two axial carbonyl substituents on the two Ru atoms. The remaining Ru atom carries two equatorial and two axial terminal carbonyl ligands. In the crystal structure, mol­ecules are linked into columns along the a axis by inter­molecular C—H⋯Cl and C—H⋯O hydrogen bonds. The mol­ecular structure is stabilized by weak intra­molecular C—H⋯O hydrogen bonds.
PMCID: PMC2979284  PMID: 21579061
24.  Ethyl (2,5-dioxo-1-phenyl-2,3-dihydro-1H,5H-1-benzofuro[3,2-d]imidazo[1,2-a]pyrimidin-3-yl)acetate 
In the title compound, C22H17N3O5, synthesized via the aza-Wittig reaction of ethyl 3-(phenyl­imino­methyl­ene­amino)­benzofuran-2-carboxyl­ate, benzene isocyanate and diethyl 2-amino­succinate, the imidazo[1,2-a]benzo[4,5]furo[2,3-d]pyrim­idine ring system is essentially planar (r.m.s. deviation for all 16 non-H atoms = 0.020 Å). The phenyl ring is twisted with respect to this ring system, making a dihedral angle of 54.23 (4)°. The crystal packing is stabilized by weak inter­molecular C—H⋯O inter­actions.
PMCID: PMC3007370  PMID: 21588454
25.  2-Amino-4-(2-chloro­phen­yl)-7,7-di­methyl-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile hemihydrate 
The asymmetric unit of the title compound, C18H17ClN2O2·0.5H2O, contains two organic mol­ecules and one solvent water mol­ecule. In each organic mol­ecule, the cyclo­hexene ring adopts an envelope conformation with the C atom connecting the two methyl groups on the flap; the 4H-pyran ring is nearly planar [maximum deviation = 0.113 (3) Å in one mol­ecule and 0.089 (3) Å in the other mol­ecule] and is approximately perpendicular to the chloro­phenyl ring [dihedral angle = 86.43 (15)° in one mol­ecule and 89.73 (15)° in the other mol­ecule]. Inter­molecular N—H⋯N, N—H⋯O, O—H⋯O and O—H⋯Cl hydrogen bonding is present in the crystal.
PMCID: PMC3297884  PMID: 22412687

Results 1-25 (105999)