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1.  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.
doi:10.1107/S1600536811031801
PMCID: PMC3200859  PMID: 22058955
2.  1-Isobutyl-N,N-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine 
In the title compound, C16H20N4, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.0719 (15) Å. An intra­molecular C—H⋯N hydrogen bond contributes to the stabilization of the mol­ecule, forming an S(6) ring motif. In the crystal, the mol­ecules are stacked along the b axis through weak aromatic π–π inter­actions between benzene and imidazole and benzene and pyridine rings [centroid–centroid distances = 3.6055 (10) and 3.5342 (10) Å, respectively].
doi:10.1107/S160053681100153X
PMCID: PMC3051498  PMID: 21523077
3.  4-Chloro­benzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate 
In the title compound, C21H20ClN5·H2O, the 1H-imidazo[4,5-c]quinoline ring is approximately planar, with a maximum deviation of 0.0795 (7) Å, and it forms a dihedral angle of 7.65 (3)° with the chloro­phenyl ring. In the crystal, the components are linked into chains along the a axis via inter­molecular N—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds. One of the H atoms of the water mol­ecule is disordered over two positions with a site-occupancy ratio of 0.80 (4):0.20 (4).
doi:10.1107/S1600536811001577
PMCID: PMC3051724  PMID: 21523079
4.  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.
doi:10.1107/S1600536814021655
PMCID: PMC4257324  PMID: 25484732
crystal structure; oxazepine; benzimidazole; angiogenesis; natural products.
5.  6-Fluoro-2-(4-meth­oxy­phen­yl)imidazo[2,1-b][1,3]benzothia­zole 
The asymmetric unit of the title compound, C16H11FN2OS, comprises two independent mol­ecules in which the benzothia­zole rings are essentially planar, with maximum deviations of 0.038 (2) and 0.045 (3) Å. The central benzothia­zole ring makes dihedral angles of 4.87 (13) and 0.64 (12)° and 4.04 (12) and 3.67 (12)° with the two terminal phenyl rings in the two independent mol­ecules. In the crystal, mol­ecules are connected via weak inter­molecular C—H⋯O hydrogen bonds forming supra­molecular chains along the c axis.
doi:10.1107/S1600536811046666
PMCID: PMC3238924  PMID: 22199773
6.  2-(7,8-Diphenyl-1H-imidazo[4,5-f]quinoxalin-2-yl)phenol methanol disolvate 
The title compound, C27H18N4O·2CH4O, is a unsymmetrically substituted quinoxaline. An intra­molecular O—H⋯N hydrogen bond involving the hydr­oxy and imino groups generates an S(6) ring motif. Inter­molecular C—H⋯O and N—H⋯O hydrogen bonds form an R 2 1(7) ring motif involving a methanol O atom and two H atoms of the imidazole and benzene rings, respectively. The latter links neighbouring mol­ecules into one-dimensional extended chains along the a axis. The two benzene rings are inclined towards each other, as indicated by the dihedral angle of 52.13 (10)°. The phenol ring is almost coplanar with the basic quinoxaline unit, making a dihedral angle of 2.43 (6)°. The short distances between the centroids of the five- and six-membered rings prove the existence of π–π inter­actions [centroid–centroid distances = 3.5234 (9)–3.7885 (10) Å]. The crystal structure is stabilized by intra­molecular O—H⋯N, inter­molecular O—H⋯O, N—H⋯O and C—H⋯O (× 2) hydrogen bonds and weak inter­molecular C—H⋯π and π–π inter­actions.
doi:10.1107/S1600536808025269
PMCID: PMC2960492  PMID: 21201724
7.  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].
doi:10.1107/S160053681003919X
PMCID: PMC3009369  PMID: 21588948
8.  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.
doi:10.1107/S1600536814017486
PMCID: PMC4186207  PMID: 25309286
crystal structure; spiro; imidazole; pyridine-indoline C—H⋯π inter­actions; hydrogen bonding
9.  tert-Butyl N-(5-bromo-1H-imidazo[4,5-b]pyridin-2-ylmeth­yl)carbamate 
In the mol­ecule of the title compound, C12H15BrN4O2, the imidazole and pyridine rings are strictly coplanar [maximum deviation 0.006 (3) Å]. In the crystal structure, mol­ecules are linked into chains running parallel to the a axis by inter­molecular N—H⋯O hydrogen bonds. Centrosymmetrically related chains are further connected by N—H⋯N hydrogen-bonding inter­actions to form a two-dimensional layer structure parallel to the ab plane.
doi:10.1107/S1600536808035393
PMCID: PMC2959901  PMID: 21581243
10.  3-{[5-(4-Bromo­phen­yl)imidazo[2,1-b][1,3,4]thia­diazol-2-yl]meth­yl}-1,2-benzoxazole 
In the title compound, C18H11BrN4OS, the imidazothia­diazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3) 0.015 (4) Å, respectively, and are inclined at an angle of 23.51 (7)° with respect to each other. The planes of the imidazothia­diazole and bromo­phenyl rings are inclined at an angle of 27.34 (3)°. In the crystal, inter­molecular C—H⋯N inter­actions result in chains of mol­ecules along the b and c axes. Moreover, C—H⋯O inter­actions result in centrosymmetric head-to-head dimers with R 2 2(24) graph-set motifs. The mol­ecular packing is further stabilized by π–π stacking inter­actions between the imidazole rings with a shortest centroid–centroid distance of 3.492 (3) Å. In addition, C—H⋯π inter­actions are observed in the crystal structure.
doi:10.1107/S1600536810052232
PMCID: PMC3050133  PMID: 21522661
11.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-(4-meth­oxy­phen­yl)sydnone 
The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intra­molecular C—H⋯O hydrogen bond stabilizes the mol­ecular structure and forms an S(6) ring motif. In the crystal packing, inter­molecular N—H⋯N hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R 2 2(8) ring motifs. The dimers are then linked into a three-dimensional network by inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds, and by C—H⋯π inter­actions. Further stabilization is provided by π–π inter­actions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.
doi:10.1107/S1600536811013900
PMCID: PMC3089192  PMID: 21754480
12.  3-[(1-Isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)amino]­benzoic acid 
In the title compound, C21H20N4O2, the statistically planar 1H-limidazole ring [maximum deviation = 0.003 (1) Å] makes dihedral angles of 1.33 (9) and 8.23 (7)°, respectively, with the essentially planar fused pyridine ring [maximum devation = 0.018 (1) Å] and the pendant benzene ring, which is attached to the pyridine ring by an —NH— group. An intra­molecular C—H⋯N inter­action, which generates an S(6) ring, helps to estalish the mol­ecular conformation. In the crystal, the mol­ecules are linked by N—H⋯O, C—H⋯O and O—H—N hydrogen bonds, which generate bifurcated R 1 2(6) and R 2 2(9) ring motifs, resulting in supra­molecular [001] chains. The crystal structure also features weak π–π stacking [centroid–centroid distance = 3.5943 (9) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536811028765
PMCID: PMC3213588  PMID: 22091165
13.  Crystal structure of (5-methyl­imidazo[1,2-a]pyridin-2-yl)methanol 
In the title compound, C9H10N2O, the imidazo[1,2-a]pyridine moiety is approximately planar (r.m.s. deviation = 0.024 Å). The methanol group is nearly perpendicular to its mean plane as indicated by the C—C—C—O and N—C—C—O torsion angles of 80.04 (16) and −96.30 (17)°, respectively. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(10) ring motif. The dimers are liked via C—H⋯O hydrogen bonds, enclosing R 2 2(10) ring motifs and forming ribbons along [201]. The ribbons are linked via a number of π–π inter­actions [centroid–centroid distances vary from 3.4819 (8) to 3.7212 (8) Å], forming a three-dimensional structure.
doi:10.1107/S1600536814023022
PMCID: PMC4257347  PMID: 25484822
crystal structure; imidazo[1,2-a]pyridine; hydrogen bonding; π–π inter­actions
14.  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].
doi:10.1107/S1600536814000695
PMCID: PMC3998316  PMID: 24764877
15.  1-(1H-Imidazo[4,5-f][1,10]phenan­throlin-2-yl)naphthalen-2-ol 
In the title mol­ecule, C23H14N4O, the dihedral angle between the pyridine rings of the phenanthroline unit is 4.43 (8)° and the dihedral angle formed by the nine essentially planar [maximum deviation 0.0389 (16)Å] non-H atoms of the benzimidazole unit and the naphthalene ring system is 74.22 (5)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯N and O—H⋯N hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536811005861
PMCID: PMC3052124  PMID: 21522467
16.  2-(4-Methyl­phen­yl)-1H-imidazo[4,5-f][1,10]phenanthroline 
In the title compound, C20H14N4, all the non-H atoms are roughly coplanar with an r.m.s. deviation of 0.0776 Å. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds, forming chains along the (). The chains are connected by inter­molecular C—H⋯N hydrogen bonds and π–π stacking inter­actions between inversion-related phenanthroline, imidazole and phenyl rings with centroid–centroid distances in the range 3.777 (1)–3.905 (1) Å.
doi:10.1107/S1600536811008853
PMCID: PMC3099870  PMID: 21754145
17.  2-Methyl-6-(trifluoro­meth­yl)imidazo[1,2-a]pyridine-3-carbonitrile 
In the title compound, C10H6F3N3, the imidazo[1,2-a]pyridine group is essentially planar with a maximum deviation of 0.021 (1) Å. The F atoms in the trifluoro­methyl group and the methyl H atoms are each disordered over two sets of sites with refined site occupancies of 0.68 (1):0.32 (1). In the crystal, mol­ecules are linked into infinite chains through two C—H⋯N inter­actions forming R 2 2(12) and R 2 2(8) hydrogen-bond ring motifs. These chains are stacked along the a axis.
doi:10.1107/S1600536811003928
PMCID: PMC3052008  PMID: 21522335
18.  5-Amino-6-benzoyl-8-nitro-2,3-di­hydro-1H-spiro­[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one dimethyl sulfoxide monosolvate 
In the title compound C21H17N5O4·C2H6OS, the central six-membered ring derived from 1,4-di­hydro­pyridine adopts a distorted boat conformation with a small puckering amplitude of 0.127 (3) Å. The sums of bond angles around the pyridine N atom [358.7 (2)°] and the other imidazolidine N atom [60 (2)°] indicate that these atoms are in sp2 hybridization, leading to an essentially planar imidazolidine ring. The last heterocycle, an oxindole moiety, is also nearly planar with an r.m.s. deviation of 0.0185 (1) Å. The amine NH2 group forms an intra­molecular hydrogen bond with the benzoyl group, giving a S(6) motif. In the crystal, N—H⋯O hydrogen bonds lead to the formation of chains along the c-axis direction. Within the chains there are further N—H⋯O and C—H⋯O hydrogen bonds enclosing R 2 2(14) ring motifs. The chains are linked via N—H⋯O and C—H⋯O hydrogen bonds involving the dimethyl sulfoxide solvent mol­ecule which acts as both an acceptor and a donor..
doi:10.1107/S1600536814008800
PMCID: PMC4011289  PMID: 24860398
19.  2-(4-tert-Butyl­phen­yl)-1H-imidazo[4,5-f][1,10]phenanthroline sesquihydrate 
In the title compound, C23H20N4·1.5H2O, the mean planes of the imidazo[4,5-f][1,10]phenanthroline system and the benzene ring make a dihedral angle of 21.76 (2)°. One water O atom lies on a twofold rotation axis. The organic mol­ecules and water mol­ecules are linked via N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯N hydrogen bonds and π–π stacking inter­actions between inversion-related phenanthroline rings complete the three-dimensional hydrogen-bonding network in the crystal structure. The stacking distance is short at 3.513 (2) Å and the perpendicular distance between the rings is 3.355 Å. The three methyl groups are disordered over two positions, with a site-occupancy ratio of 0.875 (14):0.125 (14).
doi:10.1107/S1600536809020261
PMCID: PMC2969225  PMID: 21582774
20.  3-Methyl-5-oxo-4-(2-phenyl­hydrazinyl­idene)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C11H11N5OS, the pyrazole ring is approximately planar, with a maximum deviation of 0.010 (2) Å. The dihedral angles between the benzene ring and the pyrazole and carbothio­amide groups are 5.42 (9) and 10.61 (18)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are connected by inter­molecular N—H⋯O and C—H⋯S hydrogen bonds, forming R 2 2(12) ring motifs. In addition, there is a π–π stacking inter­action [centroid–centroid distance = 3.5188 (11) Å] between the pyrazole and benzene rings. These inter­actions link the mol­ecules into infinite chains along [001].
doi:10.1107/S1600536811009779
PMCID: PMC3099837  PMID: 21754198
21.  1-[(3RS,4RS)-1-Benzyl-4-methyl­piperi­din-3-yl]-1,6-dihydro­imidazo[4,5-d]pyrrolo­[2,3-b]pyridine hemihydrate 
The benzyl residue in the title compound, C21H23N5·0.5H2O, is oriented at a dihedral angle of 83.8 (3)° towards the 1,6-dihydro­imidazo[4,5-d]pyrrolo­[2,3-b]pyridine system. The piperidine ring adopts a chair conformation with the cis substituents displaying a torsion angle of −45.91 (16)°. In the crystal, mol­ecules are accumulated as racemic dimers by two inter­molecular hydrogen bonds between the pyrrolo­pyridine systems. Another hydrogen bond is formed between the imidazole ring and the cocrystallized water mol­ecule, which is located on a twofold rotation axis.
doi:10.1107/S1600536812039980
PMCID: PMC3470401  PMID: 23125814
22.  (E)-6-Bromo-3-{2-[2-(4-chloro­benzyl­idene)hydrazin­yl]thia­zol-5-yl}-2H-chromen-2-one 
In the title compound, C19H11N3O2SClBr, the chromene ring system and the thia­zole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å, respectively. The mol­ecule adopts an E configuration about the central C=N double bond. The central thia­zole ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl ring and the chromene ring, respectively. The mol­ecular structure features a short C—H⋯O contact, which generates an S(6) ring motif. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen bonds, which link the mol­ecules into chains along the b axis. π–π stacking inter­actions [centroid-centroid distance = 3.4813 (15) Å] are also present.
doi:10.1107/S1600536811011172
PMCID: PMC3099884  PMID: 21754027
23.  6-Bromo-1,3-di-2-propynyl-1H-imidazo[4,5-b]pyridin-2(3H)-one 
The room-temperature reaction of propargyl bromide and 6-bromo-1,3-dihydro­imidazo[4,5-b]pyridin-2-one in dimethyl­formamide yields the title compound, C12H8BrN3O, which features nitro­gen-bound propynyl substituents. The imidazopyridine fused ring is almost planar (r.m.s. deviation = 0.011 Å); the propynyl chains point in opposite directions relative to the fused ring. One acetyl­enic H atom is hydrogen bonded to the carbonyl O atom of an inversion-related mol­ecule, forming a dimer; adjacent dimers are linked by a second acetyl­ene–pyridine C—H⋯N inter­action, forming a layer motif.
doi:10.1107/S1600536810007701
PMCID: PMC2983980  PMID: 21580601
24.  5-Amino-5′-bromo-6-(4-methyl­benzo­yl)-8-nitro-2,3-di­hydro-1H-spiro­[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one including an unknown solvate 
In the title compound, C22H18BrN5O4, the central six-membered ring, derived from 1,4-di­hydro­pyridine, adopts a distorted boat conformation with a puckering amplitude of 0.197 (3) Å, the imidazole ring adopts a twisted conformation with a puckering amplitude of 0.113 (3) Å, and the oxindole moiety is planar with an r.m.s. deviation of 0.0125 Å. Two intra­molecular N—H⋯O hydrogen bonds are formed, each closing an S(6) loop. In the crystal, strong N—H⋯O hydrogen bonds lead to the formation of zigzag chains along the c axis. These are consolidated in the three-dimensional crystal packing by weak N—H⋯O hydrogen bonding, as well as by C—H⋯O, C—H⋯Br and C—H⋯π inter­actions. A small region of electron density well removed from the main mol­ecule was removed with the SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155] following unsuccessful attempts to model it as a plausible solvent mol­ecule. The unit-cell characteristics do not take into account this feature of the structure.
doi:10.1107/S1600536814014391
PMCID: PMC4120621  PMID: 25161594
crystal structure
25.  Ethyl 2-[2-(3-meth­oxy­phen­yl)hydrazinyl­idene]-3-oxobutano­ate 
The title compound, C13H16N2O4, is approximately planar (r.m.s. deviation = 0.065 Å for the 19 non-H atoms). An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif and the mol­ecule adopts an E conformation with respect to the central C=N double bond. In the crystal, pairs of inter­molecular C—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers. The crystal structure also features weak C—H⋯π inter­actions.
doi:10.1107/S1600536811039444
PMCID: PMC3201266  PMID: 22065239

Results 1-25 (349137)