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1.  Crystal structure of ethyl 2-(di­eth­oxy­phosphor­yl)-2-(2,3,4-tri­meth­oxy­phen­yl)acetate 
The title compound, C17H27O8P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-tri­meth­oxy­phen­yl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of the sp 3-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the eth­oxy groups connected to the phospho­rous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three meth­oxy groups emerge out of the benzene-ring plane due to steric hindrance [C—C—O—C torsion angles = −179.9 (3)°, −52.9 (4)° and 115.3 (4)°]. In the crystal, inversion dimers linked by pairs of C—H⋯O=P hydrogen bonds generate R 2 2(14) loops. The chosen crystal was modelled as a non-merohedral twin.
PMCID: PMC4186086  PMID: 25309241
crystal structure; Michaelis–Arbuzov reaction; phosphonoacetate; non-merohedral twin; hydrogen bonds
2.  2-(3-{(3R,4R)-4-Methyl-3-[meth­yl(7H-pyrrolo­[2,3-d]pyrimidin-4-yl)amino]­piperidin-1-yl}oxetan-3-yl)aceto­nitrile monohydrate 
In the title compound, C18H24N6O·H2O, the piperidine ring adopts a chair conformation with an N—C—C—C torsion angle of 39.5 (5)° between the cis-related substituents. The pyrrole N—H group forms a water-mediated inter­molecular hydrogen bond to one of the N atoms of the annelated pyrimidine ring. The water mol­ecule connects two organic mol­ecules and is disorderd over two positions (occupancies of 0.48 and 0.52). The crystal packing shows zigzag chains of alternating organic and water mol­ecules running parallel to the a axis.
PMCID: PMC3998552  PMID: 24826108
3.  3-(4-Hexyl­oxyphen­yl)-1,2,4-triazolo[3,4-b]benzo­thia­zole 
The title compound, C20H21N3OS, was prepared by Huisgen reaction of 5-(4-hexyl­oxyphen­yl)tetra­zole and chloro­benzo­thia­zole. The essentially planar benzo­thia­zolotriazole framework [maximum deviation from the mean plane of 0.077 (1) Å for the bridgehead N atom] and the phenyl ring form a dihedral angle of 53.34 (5)°. The hex­yloxy chain adopts a gauche–all-anti conformation. The intra­centroid separation of 3.7258 (8) Å between the triazole and benzene rings is the closest contact between individual mol­ecules in the crystal.
PMCID: PMC3998472  PMID: 24764967
4.  (E)-N,N-Diethyl-2,6-diisopropyl-4-[2-(4-nitro­phen­yl)ethen­yl]aniline 
The title compound, C24H32N2O2, was prepared by Horner olefination of 4-di­ethyl­amino-3,5-diiso­propyl­benzaldehyde and diethyl p-nitro­benzyl­phospho­nate. There are two independent mol­ecules (A and B) in the asymmetric unit. Their main axes, defined by the line connecting the N atoms of the nitro and amino groups, open an angle of 79.42 (3)°. Steric hindrance around the amino group is reflected in a long aryl C—N bond [1.434 (3) Å for mol­ecule A and 1.440 (3) Å for mol­ecule B], a pyramidal geometry [angle sum = 350.0 (2)° for mol­ecule A and 349.6 (2)° for mol­ecule B], and dihedral angles between the phenyl­ene group and the plane defined by the CH2—N—CH2 unit of 86.9 (3)° for mol­ecule A and 88.3 (3)° for mol­ecule B. This gives structural support for the electronic decoupling of the amino group from the nearly planar nitro­stilbene moiety (r.m.s. deviation for C, N and O atoms = 0.097 for mol­ecule A and 0.107 Å for mol­ecule B).
PMCID: PMC3885052  PMID: 24454228
5.  tert-Butyl N-[(3R,4R)-1-(2-cyano­acet­yl)-4-methyl­piperidin-3-yl]-N-methyl­carbamate 
The piperidine ring of the title compound, C15H25N3O3, adopts a slightly distorted chair conformation with the cis substituents displaying an N—C—C—C torsion angle of 43.0 (3)°. The cyano group (plane defined by C—C—C N atoms) is bent slightly out of the plane of the amide group by 13.3 (2)°. The carbamate group is oriented at a dihedral angle of 60.3 (5)° relative to the amide group.
PMCID: PMC3685082  PMID: 23795101
6.  3,7,11-Tris{4-[(1R,3S,4S)-neomenth­yl­oxy]phen­yl}tri[1,2,4]triazolo[4,3-a:4′,3′-c:4′′,3′′-e][1,3,5]triazine–chloro­form–ethanol (1/1/1) 
The title compound, C54H69N9O3·CHCl3·C2H5OH, was prepared by a threefold nucleophilic substitution of p-neomenthyloxyphenyl­tetra­zole on cyanuric chloride followed by threefold cyclo­elimination of nitro­gen and ring closure. The central tris­triazolotriazine is roughly planar with a maximum deviation of 0.089 (7) Å but the adjacent benzene rings are twisted out of this plane. N—C—C—C torsion angles of −80.2 (9), 159.3 (7) and 50.6 (10)° destroy the formal C3 symmetry. Cavities are found between the phen­oxy residues: one is occupied by a chloro­form mol­ecule, another by ethanol forming a hydrogen bond to a triazole ring while two isopropyl groups point into the third void. One methyl group and the chloro­frm mol­ecule are disorderd and were refined using a split model.
PMCID: PMC3588459  PMID: 23476555
7.  5,11-Dimethyl-6,12-dimeth­oxy­indolo[3,2-b]carbazole 
The title compound, C22H20N2O2, was prepared in a twofold Cadogan cyclization followed by double N-methyl­ation. The crystal structure is characterized by a zigzag arrangement of centrosymmetric mol­ecules. The indolocarbazole framework is essentially planar [maximum deviation = 0.028 (2) Å] and the meth­oxy groups are orthogonal to this plane [C—C—O—C torsion angle = −88.2 (2)°]. The lengths of the C—N bonds are nearly identical and all C—C bonds of the pyrrole subunit are significantly longer than the C—C bonds in the benzene rings.
PMCID: PMC3569787  PMID: 23424533
8.  6,12-Bis(hex­yloxy)-5H,11H-indolo[3,2-b]carbazole 
The title compound, C30H36N2O2, was prepared in a twofold Cadogan cyclization. The mol­ecule is located about a center of inversion. The indolocarbazole skeleton is essentially planar [maximum deviation = 0.028 (2) Å], the C—N bond lengths are nearly identical and the C—C bond lengths of the pyrrole unit are significantly longer than those of the benzene subunits.
PMCID: PMC3588340  PMID: 23476379
9.  (Z)-1-Chloro-1-[2-(2-nitro­phen­yl)hydrazinyl­idene]propan-2-one 
The title mol­ecule, C9H8ClN3O3, lies on a mirror plane. Intra­molecular N—H⋯O and N—H⋯Cl hydrogen bonds occur. One of the nitro O atoms is disordered (site occupancy ratio = 0.40:0.10).
PMCID: PMC3588268  PMID: 23476453
10.  2-[5-Bromo-1-(3-chloro­benz­yl)-2-methyl-1H-indol-3-yl]acetic acid 
In the title compound, C18H15BrClNO2, the indole ring system forms a dihedral angle of 86.9 (2)° with the 3-chloro­benzyl ring. In the crystal, mol­ecules form inversion dimers connected via pairs of O—H⋯O hydrogen bonds.
PMCID: PMC3588987  PMID: 23476223
11.  3-(4-Bromo­phen­yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
The asymmetric unit of the title compound, C16H11BrN2O, contains two independent mol­ecules with slightly different geometries. The 4-bromo­benzene ring forms dihedral angles of 26.0 (2) and 39.9 (7)° with the pyrazole ring in the two mol­ecules while the phenyl ring is oriented at 19.7 (5) and 7.3 (0)° with respect to the pyrazole ring.
PMCID: PMC3588988  PMID: 23476224
12.  1-Benzyl-1H-benzotriazole 3-oxide monohydrate 
In the title hydrate, C13H11N3O·H2O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007 Å) and is almost orthogonal to the phenyl ring to which it is linked by a methyl­ene group, forming a dihedral angle of 81.87 (15)°. In the crystal, mol­ecules are linked into chains along [001] by O—H⋯O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯O, C—H⋯π and π–π [centroid–centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595 (3) Å] inter­actions.
PMCID: PMC3588841  PMID: 23468806
13.  N-[(3RS,4RS)-1-Benzyl-4-methyl­piperidin-3-yl]-5-nitro-1-phenyl­sulfonyl-1H-pyrrolo­[2,3-b]pyridine-4-amine 
The pyrrolo­pyridine system in the title compound, C27H29N5O4S, is oriented at a dihedral angle of 71.20 (5)° towards the phenyl ring of the tosyl residue and at a dihedral angle of 45.43 (4)° towards the benzyl group. The structure shows an intra­molecular N—H⋯O and a weak intra­molecular N—H⋯N hydrogen bond. The piperidine ring adopts a chair conformation, with the cis substituents displaying a torsion angle of −54.59 (18)°.
PMCID: PMC3470400  PMID: 23125813
14.  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.
PMCID: PMC3470401  PMID: 23125814
15.  N-[(3RS,4SR)-1-Benzyl-4-methyl­piperi­din-3-yl]-1-(4-methylphenyl­sulfonyl)-5-nitro-1H-pyrrolo­[2,3-b]pyridin-4-amine 
The structure of the title compound, C27H29N5O4S, displays an intra­molecular N—H⋯O hydrogen bond. The pyrrolo­[2,3-b]pyridine core makes a dihedral angle of 85.5 (4)° with the benzyl residue and a dihedral angle of 89.4 (9)° with the tosyl ring. The nitro group is slightly twisted out of the plane of the planar pyrrolo­pyridine system [(—N—)C—C—N—O torsion angle = −4.61 (18)° and (—NH—)C—C—N—O = −6.46 (18)°].
PMCID: PMC3470359  PMID: 23125772
16.  (2E,4R,5R,6S)-2-(4,5,6-Trihy­droxy­cyclo­hex-2-en-1-yl­idene)acetonitrile 
The crystal structure of the title compound, C8H9NO3, is characterized by a complex three-dimensional hydrogen-bond network in which every mol­ecule is connected to six symmetry-related neighbours.
PMCID: PMC3435749  PMID: 22969620
17.  4-(4-Fluoro­phen­yl)-3-(pyridin-4-yl)-1-(2,4,6-trichloro­phen­yl)-1H-pyrazol-5-amine 
In the title compound, C20H12Cl3FN4, the pyrazole ring forms dihedral angles of 47.51 (9), 47.37 (9) and 74.37 (9)° with the directly attached 4-fluoro­phenyl, pyridine and 2,4,6-trichloro­phenyl rings, respectively. Only one of the two amino H atoms is involved in hydrogen bonding. The crystal packing is characterized by N—H⋯N hydrogen bonds, which result in infinite chains parallel to the c axis.
PMCID: PMC3435635  PMID: 22969508
18.  1-Benzyl-1H-benzotriazole 3-oxide–1-hy­droxy-1H-benzotriazole (1/1) 
In the title compound, C6H5N3O·C13H11N3O, the benzo­triazole ring system in the 1-benzyl-1H-benzotriazole 3-oxide (A) mol­ecule is close to being planar (r.m.s. deviation = 0.011 Å); its mean plane forms a dihedral angle of 67.56 (7)° with that of the attached phenyl ring. The benzotriazole ring system in the 1-hy­droxy­benzotriazole (B) mol­ecule is also close to being planar (r.m.s. deviation = 0.010 Å). In the crystal, weak C—H⋯O and C—H⋯π inter­actions are present. The A and B molecules are linked by an O—H⋯N hydrogen bond.
PMCID: PMC3414323  PMID: 22904856
19.  1-Benz­yloxy-1H-benzotriazole 
In the title compound, C13H11N3O, the dihedral angle between the benzotriazole ring system [maximum deviation = 0.027 (16) Å] and the benzene ring is 10.28 (9)°. The C—C—O—N bond adopts an anti conformation [torsion angle = −177.11 (16)°]. In the crystal, the mol­ecules inter­act via weak C—H⋯π inter­actions and aromatic π–π stacking [centroid-to-centroid distance = 3.731 (12) Å].
PMCID: PMC3394030  PMID: 22798895
20.  Decachloro­hexa-1,5-diene 
The title compound, C6Cl10, cystallizes in a nearly C2-symmetrical gauche conformation. Both trichloro­vinyl groups are nearly planar [Cl—C—C—Cl torsion angles = −178.47 (12) and −179.93 (11)°] and the lengths of their C—Cl bonds increase from the terminal trans and cis C—Cl bonds to the inter­nal bonds. The Cl—C—Cl bond angles of the terminal dichloro­methyl­ene units are compressed to 111.75 (11) and 111.40 (11)°.
PMCID: PMC3379281  PMID: 22719479
21.  2,7-Bis(2-nitro­phen­yl)-9-octyl-9H-carbazole 
The title compound, C32H31N3O4, was obtained in a Suzuki coupling of carbazole diboronic acid and bromo­nitro­benzene. In the crystal, the mol­ecule adopts a non-symmetric conformation. The carbazole ring system is approximately planar [maximum deviation from the least-squares plane = 0.039 (2) Å]. The planes of the carbazole unit and the benzene rings subtend dihedral angles of 48.42 (7) and 41.81 (6)°. The dihedral angles between the planes of the nitro­phenyl rings and the nitro groups are 44.34 (19) and 61.64 (15)°. The crystal is built from two strands of parallel mol­ecules with inter­digitated octyl chains. These strands are symmetry related by a twofold screw axis.
PMCID: PMC3344178  PMID: 22606181
22.  1-Benzyl-1H-benzotriazole 
In the title compound, C13H11N3, the benzotriazole ring system is essentially planar, with a maximum deviation of 0.0173 (18) Å, and forms a dihedral angle of 75.08 (8)Å with the phenyl ring. In the crystal, pairs of weak C—H⋯N hydrogen bonds form inversion dimers. In addition, there are weak C—H⋯π(arene) inter­actions and weak π–π stacking inter­actions, with a centroid–centroid distance of 3.673 (11) Å.
PMCID: PMC3344078  PMID: 22589987
23.  4-[2-(Benzyl­amino)­phen­yl]-2,6-dimethyl­quinoline N-oxide 
The title compound, C24H22N2O, was obtained in a two-step procedure from the corresponding 4-(2-iodo­phen­yl)quinoline. The quinoline system is approximately planar [maximum deviation from the least-squares plane = 0.021 (2) Å]. The planes of the quinoline system and the phenyl ring subtend a dihedral angle of 78.08 (8)°. In the crystal, pairs of mol­ecules are connected via a center of symmetry and linked by a pair of angular N—H⋯O hydrogen bond. These dimers form columns oriented along the c axis.
PMCID: PMC3344055  PMID: 22589964
24.  1,4-Dihex­yloxy-2,5-bis­(2-nitro­phen­yl)benzene 
The title compound, C30H36N2O6, was prepared via twofold Suzuki coupling of a diboronic acid with bromo­nitro­benzene. The mol­ecule is located on a crystallographic inversion centre. The lateral benzene ring and the central ring make a dihedral angle of 48.75 (14)° and the nitro group is twisted by 41.47 (13)° out of the plane of the benzene ring. The nitro and hex­yloxy groups are in close proximity and the hex­yloxy chain adopts an all-anti conformation.
PMCID: PMC3343986  PMID: 22589895
25.  4-[5-Amino-4-(4-fluoro­phen­yl)-3-(pyridin-4-yl)-1H-pyrazol-1-yl]benzo­nitrile 
In the crystal structure of the title compound, C21H14FN5, the pyrazole ring forms dihedral angles of 38.0 (1), 40.0 (1) and 28.5 (1)° with the directly attached 4-fluoro­phenyl, pyridine and benzonitrile rings, respectively. The crystal packing is characterized by N—H⋯N hydrogen bonds, which result in a two-dimensional network parallel to the ac-plane.
PMCID: PMC3343917  PMID: 22589998

Results 1-25 (101)