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1.  (2S,3R)-tert-Butyl N-[4-(N-benzyl-4-fluoro­benzene­sulfonamido)-3-hy­droxy-1-phenyl­butan-2-yl]carbamate 
In the title mol­ecule, C28H33FN2O5S, the mean plane about the tertiary amine group (sum of the angles subtended at the sp 2-hybridized N atom = 359.7°) forms a dihedral angle of 16.66 (6)° with the phenyl ring adjacent to the carbamate group. The sulfonamide benzene ring and the hy­droxy group lie to either side of the C2NS plane, whereas the benzyl­phenyl (connected to the N atom) and carbamate substituents lie to the other side. Supra­molecular layers propagating in the ac plane are found in the crystal, linked by hy­droxy–sulfonamide O—H⋯O and carbamate–carbamate N—H⋯O hydrogen bonds along with C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536812011440
PMCID: PMC3344084  PMID: 22606087
2.  Crystal structure of [(2S)-1-[(3S)-3-carboxy-6,7-dimethoxy-1,2,3,4-tetra­hydroisoquinolin-2-yl]-1-oxopropan-2-yl][(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]azanium chloride acetonitrile monosolvate 
The title compound (trivial name moexipril hydro­chloride) crystallizes as the aceto­nitrile monosolvate, C27H35N2O7 +·Cl−·C2H3N, with the salt comprising a U-shaped cation and a chloride anion. The conformation of the cation is stabilized by a weak intra­molecular N+—H⋯O hydrogen bond and the tetra­hydro­pyridine ring adopts a boat conformation. The dihedral angle between the planes of the benzene rings is 85.6 (1)°. In the crystal, the cations and anions form tight ionic pairs by strong inter­molecular O—H⋯Cl hydrogen bonds. C—H⋯Cl and C—H⋯N hydrogen bonds link these ionic pairs and the aceto­nitrile solvate mol­ecules into puckered layers parallel to (100).
doi:10.1107/S160053681402090X
PMCID: PMC4257232  PMID: 25484709
crystal structure; moexipril hydro­chloride; hydrogen bond
3.  (η5-Penta­methyl­cyclo­penta­dien­yl)(η6-4-phenyl­butan-2-one)ruthenium(II) tetra­phenyl­borate 
The title compound, [Ru(C10H15)(C10H12O)][B(C6H5)4], crystallizes as discrete (η5-penta­methyl­cyclo­penta­dien­yl)Ru(η6-4-phenyl­butan-2-one)]+ cations and [BPh4]− anions. In the cation, the non-H atoms of the butan-2-one group are approximately planar (r.m.s. deviation = 0.056 Å) and lie nearly perpendicular to the plane of the phenyl ring with a dihedral angle between the two planes of 69.3 (1)°. No significant C—H⋯O inter­actions are observed between the methyl and phenyl H atoms and the carbonyl O atom.
doi:10.1107/S1600536810046064
PMCID: PMC3011665  PMID: 21589253
4.  (E)-1-Phenyl­butan-2-one (2,4-dinitro­phen­yl)hydrazone 
In the title compound, C16H16N4O4, the dihedral angle between the aromatic rings is 79.04 (8)° and an intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, weak C—H.·O and C—H..π inter­actions link the mol­ecules, forming sheets.
doi:10.1107/S1600536809041178
PMCID: PMC2971069  PMID: 21578325
5.  7-(4-Methoxy­phen­yl)-5-methyl-9-phenyl-7H-pyrrolo[2′,3′:4,5]pyrimido[1,6-d]tetrazole 
The title compound, C20H16N6O, is composed of a tetra­zolo ring and a 4-methoxy­phenyl and a benzene-substituted pyrrole ring at the 7 and 9 positions fused to a pyrimidine ring in a nearly planar fashion [maximum deviation of 0.018 (1) Å for the fused ring system]. A methyl group at the 5 position is also in the plane of the hetero cyclic system. The dihedral angle between the mean planes of the benzene and 4-methoxy­phenyl rings is 40.4 (2)°. The dihedral angles between the mean planes of the pyrimidine and the benzene and 4-methoxy­phenyl rings are 15.6 (5)° and 52.6 (7)°, respectively. A weak intra­molecular C—H⋯N hydrogen bond inter­action, which forms an S(7) graph-set motif, helps to establish the relative conformations of the tetrazolo and benzene rings. In the crystal, weak inter­molecular C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 3.5270 (16), 3.5113 (16), 3.7275 (17) and 3.7866 (17) Å] link the mol­ecules into a two-dimensional array obliquely parallel to (101) and propagating along the b axis.
doi:10.1107/S1600536809053653
PMCID: PMC2980237  PMID: 21580097
6.  3-(2,6-Dioxopiperidin-3-yl)-3-aza­bicyclo­[3.2.0]heptane-2,4-dione 
The title mol­ecule, C11H12N2O4, consists of a 3-aza­bicyclo­[3.2.0]heptane group containing a nearly planar cyclo­butane ring (r.m.s. deviation of fitted atoms is 0.0609 Å), fused to a pyrrolidine ring, bonded to a 2,6-dioxopiperidine ring at the 3-position. The angle between the mean planes of the cyclo­butane and fused pyrrolidine ring is 67.6 (6)°. The dihedral angles between the mean planes of the pyrrolidine and cyclo­butane rings and the dioxopiperidine ring are 73.9 (2) and 62.4 (4)°, respectively. The pyrrolidine and dioxopiperidine rings are twisted about the 3-yl group [torsion angles = −55.0 (1) and 115.0 (1)°] in a nearly perpendicular manner. Crystal packing is influenced by extensive inter­molecular C—H⋯O and N—H⋯O inter­actions between all four carbonyl O atoms and H atoms from the cyclo­butane and dioxopiperidine rings, as well as between the N atom and an H atom from the cyclo­butane ring. In addition, weak π-ring interactions also occur between H atoms from the cyclobutane ring and the five-membered pyrrolidine ring. As a result, mol­ecules are linked into infinite chains diagonally along the [101] plane of the unit cell in an alternate inverted pattern.
doi:10.1107/S1600536809002839
PMCID: PMC2968123  PMID: 21581989
7.  {5,5′-Dihydr­oxy-2,2′-[o-phenyl­enebis­(nitrilo­methyl­idyne)]diphenolato}nickel(II) dihydrate 
In the title complex, [Ni(C20H14N2O4)]·2H2O, the NiII ion is in an essentially square-planar geometry involving an N2O2 atom set of the tetra­dentate Schiff base ligand. The Ni atom lies on a crystallographic twofold rotation axis. The asymmetric unit contains one half-mol­ecule of the complex and a water mol­ecule. An inter­molecular O—H⋯O hydrogen bond forms a four-membered ring, producing an R 1 2(4) ring motif involving a bifurcated hydrogen bond to the phenolate O atoms of the complex mol­ecule. In the crystal structure, mol­ecules are linked by π–π stacking inter­actions, with centroid–centroid distances in the range 3.5750 (11)–3.7750 (11) Å. As a result of the twofold symmetry, the central benzene ring makes the same dihedral angle of 15.75 (9)° with the two outer benzene rings. The dihedral angle between the two hydroxy­phenyl rings is 13.16 (5)°. In the crystal structure, mol­ecules are linked into infinite one-dimensional chains by directed four-membered O—H⋯O—H inter­actions along the c axis and are further connected by C—H⋯O and π–π stacking into a three-dimensional network. An inter­esting feature of the crystal structure is the short Ni⋯O, O⋯O and N⋯N inter­actions which are shorter than the sum of the van der Waals radii of the relevant atoms. The crystal structure is stabilized by inter­molecular O—H⋯O and C—H⋯O hydrogen bonds and by π–π stacking inter­actions.
doi:10.1107/S1600536808026093
PMCID: PMC2960688  PMID: 21201624
8.  A series of N-(2-phenyl­ethyl)nitro­aniline derivatives as precursors for slow and sustained nitric oxide release agents 
A series of N-(2-phenyl­ethyl)nitro­aniline derivatives is presented, demonstrating that modest changes in the functional groups cause significant differences in mol­ecular conformation, inter­molecular inter­actions and packing.
2,4-Di­nitro-N-(2-phenyl­ethyl)aniline, C14H13N3O4, (I), crystallizes with one independent mol­ecule in the asymmetric unit. The adjacent amine and nitro groups form an intra­molecular N—H⋯O hydrogen bond. The anti conformation about the ethyl C—C bond leads to the phenyl and aniline rings being essentially parallel. Mol­ecules are linked into dimers by inter­molecular N—H⋯O hydrogen bonds, such that each amine H atom participates in a three-centre inter­action with two nitro O atoms. Though the dimers pack so that the arene rings of adjacent mol­ecules are parallel, the rings are staggered and π–π inter­actions do not appear to be favoured. 4,6-Di­nitro-N,N′-bis­(2-phenyl­ethyl)benzene-1,3-di­amine, C22H22N4O4, (II), differs from (I) in the presence of a second 2-phenyl­ethyl­amine group on the substituted ring. Compound (II) also crystallizes with one unique mol­ecule in the asymmetric unit. Both amine groups are involved in intra­molecular N—H⋯O hydrogen bonds with adjacent nitro groups. Although one ethyl group adopts an anti conformation as in (I), the other is gauche, with the result that the pendant phenyl rings are not parallel. The amine group that is part of the gauche conformation participates in a three-centre N—H⋯O hydrogen bond with the nitro group of a neighbouring mol­ecule, leading to dimers as in (I). The other amine H atom does not form any inter­molecular hydrogen bonds. The packing leads to separations of ca 3.4 Å of the parallel anti phenyl and amino­benzene rings. 2-Cyano-4-nitro-N-(2-phenyl­ethyl)aniline, C15H13N3O2, (III), differs from (I) only in having a cyano group in place of the 2-nitro group. The absence of the adjacent nitro group eliminates the intra­molecular N—H⋯O hydrogen bond. Mol­ecules of (III) adopt the same anti conformation about the ethyl group as in (I), but crystallize in the higher-symmetry monoclinic space group P21/n. The mol­ecules are linked into dimers via N—H⋯N amine–cyano hydrogen bonds, while the nitro groups are not involved in any N—H⋯O inter­actions. Owing to the different symmetry, the mol­ecules pack in a herringbone pattern with fewer face-to-face inter­actions between the rings. The closest such inter­actions are about 3.5 Å between rings that are largely slipped past one another. 4-Methyl­sulfonyl-2-nitro-N-(2-phenyl­ethyl)aniline, C15H16N2O4S, (IV), differs from (I) in having a methyl­sulfonyl group in place of the 4-nitro group. The intra­molecular N—H⋯O hydrogen bond is present as in (I). However, unlike (I), the conformation about the ethyl group is gauche, so the two arene rings are nearly per­pen­dicular rather than parallel. The packing is significantly different from the other three structures in that there are no inter­molecular hydrogen bonds involving the N—H groups. The mol­ecules are arranged in tetra­gonal columns running along the c axis, with the aniline rings mostly parallel and separated by ca 3.7 Å. Taken together, these structures demonstrate that modest changes in functional groups cause significant differences in mol­ecular conformation, inter­molecular inter­actions and packing.
doi:10.1107/S0108270113025869
PMCID: PMC3818095  PMID: 24192194
crystal structure; N-(2-phenyl­ethyl)nitro­aniline derivatives; secondary amines; nitric oxide release agents
9.  2-Amino-1H-benzoimidazol-3-ium 4,4,4-trifluoro-1,3-dioxo-1-phenyl­butan-2-ide 
In the title compound, C7H8N3 +·C10H6F3O2 −, 1H-benzoimidazol-2-amine system adopts a planar conformation with an r.m.s. deviation of 0.0174 Å. The cation and anion in the asymmetric unit are linked by N—H⋯O hydrogen bonds. There are also additional inter­molecular N—H⋯O hydrogen bonds and π–π stacking inter­actions between the phenyl rings of neighbouring anions with centroid–centroid distances of 4.0976 (13) Å.
doi:10.1107/S1600536808037483
PMCID: PMC2959878  PMID: 21581428
10.  Crystal structure of 2-hy­droxy­imino-2-(pyridin-2-yl)-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide 
The mol­ecule of the title compound is approximately planar with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. In the crystal, mol­ecules are linked by bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers, which are in turn linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502).
The mol­ecule of the title compound, C14H13N5O2, is approximately planar (r.m.s deviation for all non-H atoms = 0.093 Å), with the planes of the two pyridine rings inclined to one another by 5.51 (7)°. The oxime group is syn to the amide group, probably due to the formation of an intra­molecular N—H⋯N hydrogen bond that forms an S(6) ring motif. In the crystal, mol­ecules are linked by pairs of bifurcated O—H⋯(O,N) hydrogen bonds, forming inversion dimers. The latter are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming sheets lying parallel to (502). The sheets are linked via π–π stacking inter­actions [inter-centroid distance = 3.7588 (9) Å], involving the pyridine rings of inversion-related mol­ecules, forming a three-dimensional structure.
doi:10.1107/S1600536814025793
PMCID: PMC4257442  PMID: 25552998
crystal structure; hy­droxy­imino; acetohydrazide; pyridyl­ethyl­idene; hydrogen bonding; π–π stacking inter­actions
11.  (E)-2-[1-(1-Benzothio­phen-2-yl)ethyl­idene]-N-phenyl­hydrazinecarboxamide 
The title compound, C17H15N3OS, crystallizes with two unique mol­ecules, denoted 1 and 2, in the asymmetric unit. The two mol­ecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both mol­ecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothio­phene groups and N-bound phenyl rings are 36.36 (9)° for mol­ecule 1 and 29.71 (9)° for mol­ecule 2. The C=N—NH—C(O)NH ethyl­idene–hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 Å, respectively, for the two mol­ecules. The methyl substituents lie 0.338 (3) and 0.396 (3) Å, respectively, from these planes. The C=N—NH—C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)°, respectively, in mol­ecules 1 and 2. This conformation is enhanced by weak intra­molecular C—H⋯O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each mol­ecule. In the crystal, pairs of mol­ecules are linked by pairs of inter­molecular N—H⋯O hydrogen bonds into dimers. Alternating dimers are further inter­connected by weak C—H⋯O contacts into zigzag rows along b. The rows are stacked along a by C—H⋯π contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothio­phene units.
doi:10.1107/S1600536811037457
PMCID: PMC3201294  PMID: 22058789
12.  5,5′-Dimeth­oxy-2,2′-[(nonane-1,9-diyldi­oxy)bis­(nitrilo­methyl­idyne)]diphenol 
The mol­ecule of the title compound, C25H34N2O6, adopts a fully extended configuration. The oxime (—CH=N—O—) group is coplanar with the aromatic ring and the two benzene rings are almost parallel, making a dihedral angle of 0.16 (3)°. In the crystal structure, strong intra­molecular O—H⋯N hydrogen bonds generate six-membered S(6) ring motifs. Inter­molecular C—H⋯O hydrogen bonds link each mol­ecule to five others, forming an infinite three-dimensional supra­molecular structure. The crystal is further stabilized by π–π stacking inter­actions between neighbouring benzene rings [centroid–centroid distance = 3.744 (2) Å].
doi:10.1107/S1600536809041038
PMCID: PMC2971058  PMID: 21578365
13.  5-[(4-Fluoro­anilino)meth­yl]-6-methyl-N-(4-methyl­phen­yl)-2-phenyl­pyrimidin-4-amine 
In the title compound, C25H23FN4, the pyrimidine ring makes dihedral angles of 11.3 (2), 24.5 (2) and 70.1 (2)° with the phenyl and two benzene rings, and the mol­ecular conformation is stabilized by an intra­molecular N—H⋯N hydrogen bond with an S(6) ring motif. In the crystal, a pair of weak C—H⋯F hydrogen bonds link two mol­ecules into an inversion dimer with an R 2 2(16) motif. In the dimer, there is also an inter­molecular π–π stacking inter­action [centroid–centroid distance = 3.708 (4) Å] between the fluorinated benzene rings. The dimers are further linked by a C—H⋯π inter­action, so forming a column along the c axis.
doi:10.1107/S160053681203783X
PMCID: PMC3470299  PMID: 23125712
14.  1,8-Bis(4-amino­benzo­yl)-2,7-dimeth­oxy­naphthalene 
The title compound {systematic name: [8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C26H22O4N2, possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis. In the crystal, the mol­ecules inter­act through inter­molecular N—H⋯O hydrogen bonds between the amino and meth­oxy groups on the naphthalene ring systems and N—H⋯π inter­actions between the amino groups and the naphthalene rings. Furthermore, weak C—H⋯O hydrogen bonds and π–π stacking inter­actions between the benzene rings are observed. The centroid–centroid and inter­planar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent mol­ecules are 3.6954 (8) and 3.2375 (5) Å, respectively. The dihedral angle between the mean planes of the benzene ring and the naphthalene ring system is 83.59 (5)°. The benzene ring and the carbonyl group in the benzoyl unit are almost coplanar [C—C—C—O torsion angle = 175.91 (10)°].
doi:10.1107/S1600536810041346
PMCID: PMC3009325  PMID: 21589080
15.  (1R*,2R*)-1-(7-Bromo-3-methoxy­naphthalen-2-yl)-4-(dimethyl­amino)-2-(naphthalen-1-yl)-1-phenyl­butan-2-ol 
In the crystal structure of the title compound, C33H32BrNO2, the naphthalene ring system and the benzene ring are oriented at dihedral angles of 82.24 (4) and 79.53 (4)°, respectively, to the quinoline ring system. An intra­molecular O—H⋯N hydrogen bond occurs between the hydr­oxy H atom and the amine N atom.
doi:10.1107/S1600536810005209
PMCID: PMC2983564  PMID: 21580392
16.  5-[(3,5-Dichloro­anilino)meth­yl]-N-(3,5-dichloro­phen­yl)-6-methyl-2-phenyl­pyrimidin-4-amine 
In the title compound, C24H18Cl4N4, the pyrimidine ring makes dihedral angles of 19.1 (2), 4.1 (2) and 67.5 (2)°, respectively, with phenyl and two benzene rings, and the mol­ecular conformation is stabilized by an intra­molecular N—H⋯N hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of inter­molecular N—H⋯N hydrogen bonds connect two mol­ecules, forming inversion dimers with R 2 2(12) motifs. C—H⋯π inter­actions links the dimers into a chain running along the a-axis direction. There are also π–π stacking inter­actions [centroid–centroid distance = 3.666 (4) Å] between the benzene rings of adjacent chains.
doi:10.1107/S160053681204665X
PMCID: PMC3588999  PMID: 23476235
17.  (E)-N′-(4-Meth­oxy­benzyl­idene)-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide 
In the title compound, C14H15N5O4, the central –C=N—N—C(=O)—C– bridge is nearly planar [maximum deviation = 0.037 (1) Å] and forms dihedral angles of 7.37 (9) and 73.33 (5)°, respectively, with the benzene and imidazole rings. The dihedral angle between the benzene and imidazole rings is 66.08 (9)°. The meth­oxy and nitro groups are nearly coplanar with the benzene and imidazole rings, respectively, with a C—O—C—C torsion angle of 5.9 (2)° and an O—N—C—C angle of −0.2 (2)°. In the crystal, mol­ecules are linked by a pair of N—H⋯O hydrogen bonds with an R 2 2(8) ring motif, forming an inversion dimer. The dimers are further inter­connected by C—H⋯O hydrogen bonds into a sheet parallel to the (111) plane. A C—H⋯π inter­action is also observed between the sheets.
doi:10.1107/S1600536812039621
PMCID: PMC3470350  PMID: 23125763
18.  4-Cyclo­butyl­amino-3-nitro­benzoic acid 
The asymmetric unit of the title compound, C11H12N2O4, contains two crystallographically independent mol­ecules with similar geometries. Both mol­ecules contain an intra­molecular N—H⋯O hydrogen bond. The dihedral angles between the benzene ring and the mean plane of the cyclo­butane ring are 38.29 (7) and 57.04 (8)° in the two mol­ecules, and the nitro group is twisted slightly away from the plane of the benzene ring [dihedral angles = 9.15 (12) and 9.55 (12)° in the two mol­ecules]. In the crystal, the independent mol­ecules are linked into dimers by O—H⋯O hydrogen bonds between their carboxyl groups, and C—H⋯O and C—H⋯π inter­actions are formed between dimers.
doi:10.1107/S1600536809021412
PMCID: PMC2969240  PMID: 21582847
19.  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
20.  Crystal structure of dimethyl 3,3′-[(4-chloro­phen­yl)methyl­ene]bis­(1H-indole-2-carboxyl­ate) 
In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming inversion dimers, which are linked by a further N—H⋯O hydrogen bond, forming chains along [100]. There are intra- and inter­molecular C—H⋯π inter­actions present, the latter linking the chains to form a three-dimensional supra­molecular structure.
In the title compound, C27H21ClN2O4, the mean planes of the two indole ring systems (r.m.s. deviations = 0.021 and 0.024 Å) are approximately perpendicular to one another, with a dihedral angle of 79.54 (12)°. The benzene ring is twisted with respect to the mean planes of the two indole ring systems at angles of 80.14 (15) and 86.30 (15)°. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(18) ring motif. The dimers are linked by a further N—H⋯O hydrogen bond, forming chains along [100]. There are intra- and inter­molecular C—H⋯π inter­actions present, the latter linking the chains to form a three-dimensional supra­molecular structure.
doi:10.1107/S1600536814020686
PMCID: PMC4257187  PMID: 25484668
crystal structure; indole; bis-indolymethane; MRI contrast agent; N—H⋯O hydrogen bonds; C—H⋯π inter­actions
21.  (2,4-Dihy­droxy-6-meth­oxy­phen­yl)(3,5-dihy­droxy­phen­yl)methanone monohydrate 
The title benzophenone compound, C14H12O6·H2O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The mol­ecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The meth­oxy group is approximately coplanar with the attached benzene ring, with a C—O—C—C torsion angle of 1.91 (18)°. The water mol­ecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by inter­molecular O—H⋯O hydrogen bonds. These inter­actions link the mol­ecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π–π inter­actions, with centroid–centroid distances of 3.6219 (7) Å. A weak O—H⋯π inter­action was also noted.
doi:10.1107/S1600536811037913
PMCID: PMC3201278  PMID: 22065717
22.  2-[2-Chloro-5-(trifluoro­methyl)­phen­yl]hexa­hydro­pyrimidine monohydrate 
The mol­ecule of the title compound, C11H12ClF3N2·H2O, is a substituted hexa­hydro­pyrimidine. There are two crystallographically independent mol­ecules (A and B) and two water mol­ecules in the asymmetric unit of the title compound. Inter­molecular C—H⋯Cl (× 2), C—H⋯F, and C—H⋯N (× 2) hydrogen bonds generate S(5) ring motifs. The dihedral angle between the two benzene rings is 8.17 (11)°. The F atoms in mol­ecule B are disordered over four positions with refined site-occupancies of ca 0.35/0.19/0.29/0.17 for the four components. In the crystal structure, mol­ecules are arranged into one-dimensional extended chains along the c axis and are further stacked along the a axis by directed four-membered O—H⋯O—H inter­actions, forming two-dimensional networks parallel to the ac plane. The short distances between the centroids of the benzene rings (3.8002–3.8327 Å) indicate the existence of π–π inter­actions. In addition, the crystal structure is further stabilized by N—H⋯O, O—H⋯N (× 4), N—H⋯Cl and C—H⋯O (× 2) hydrogen-bonding inter­actions.
doi:10.1107/S1600536808027232
PMCID: PMC2960557  PMID: 21201812
23.  2-Methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol–2-methyl-6-(5-methyl-1H-benzimidazol-2-yl)phenol (3/1) 
The title compound, 0.75C15H14N2O·0.25C15H14N2O, is a co-crystal of 2-methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol as the major component and 2-methyl-6-(5-methyl-1H-benz­imidazol-2-yl)phenol as the minor component. The refined site-occupancy ratio is 0.746 (4)/0.254 (4). The conformations of both components are identical except for that of the methyl substituent on the benzene ring of the benzimidazole unit which is positionally disordered over two positions. The mol­ecule is essentially planar, the dihedral angle between the benzimidazole plane and the benzene ring being 3.49 (4)°. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal packing, mol­ecules are linked through N—H⋯O hydrogen bonds into chains along [201]. These chains are stacked approximately along the a-axis direction. The crystal packing is further stabilized by weak N—H⋯O and O⋯H⋯N hydrogen bonds, together with weak inter­molecular C—H⋯π inter­actions. A π–π inter­action with a centroid–centroid distance of 3.6241 (6) Å is also observed between the substituted phenyl ring and that of the benzimidazole system.
doi:10.1107/S1600536809049770
PMCID: PMC2972110  PMID: 21578934
24.  5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination 
The title compound, C18H21N3O3, is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007 ▶). Acta Cryst. E63, o4782–o4782]. Using the whole mol­ecule disorder, R values are much smaller than those published. An intra­molecular O—H⋯N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The dihedral angle between the mean plane of the two benzene rings (major component) is 9.0 (5)°. The crystal structure shows short C⋯C [3.189 (15)–3.298 (12) Å] and C⋯O [2.983 (5)–3.149 (13) Å] contacts. Inter­molecular C—H⋯O inter­actions link neighbouring mol­ecules into dimers with R 2 2(18) motifs. In the crystal structure, these dimers are linked together by inter­molecular C—H⋯O inter­actions into one-dimensional extended chains along the b axis. The crystal structure is further stabilized by inter­molecular π–π stacking inter­actions [centroid–centroid distances = 3.458 (8)–3.691 (6) Å].
doi:10.1107/S1600536809001731
PMCID: PMC2968344  PMID: 21581950
25.  Tris{2-[(2-amino­benzyl­idene)amino]­ethyl}amine 
The title Schiff base, C27H33N7, is a tripodal amine displaying C 3 symmetry, with the central tertiary N atom lying on the threefold crystallographic axis. The N—CH2—CH2—N conformation of the pendant arms is gauche [torsion angle = 76.1 (3)°], which results in a claw-like mol­ecule, with the terminal aniline groups wrapped around the symmetry axis. The lone pair of the apical N atom is clearly oriented inwards towards the cavity, and should thus be chemically inactive. The amine NH2 substituents lie in the plane of the benzene ring to which they are bonded. With such an arrangement, one amine H atom forms an S(6) motif through a weak N—H⋯N hydrogen bond with the imine N atom, while the other is engaged in an inter­molecular N—H⋯π contact involving the benzene ring of a neighbouring mol­ecule related by inversion. The benzene rings also participate in an intra­molecular C—H⋯π contact of similar strength. In the crystal structure, mol­ecules are separated by empty voids (ca 5% of the crystal volume), although the crystal seems to be unsolvated.
doi:10.1107/S1600536810043783
PMCID: PMC3011466  PMID: 21589366

Results 1-25 (348947)