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1.  1-(2-Methyl­benzo­yl)-3-m-tolyl­thio­urea 
The molecule of the title compound, C16H16N2OS, is not planar; the two aromatic rings are inclined to one another by 37.59 (9)°. There are intra­molecular hydrogen bonds between the benzoyl O atom and the H atom of the thio­amide N atom, and between the thio­urea S atom and the H atom of the tolyl group. These hydrogen bonds stabilize the mol­ecule in such a way that the thio­urea group adopts a trans–cis geometry. In the crystal structure, mol­ecules are linked by N—H⋯S inter­molecular hydrogen bonds, forming centrosymmetric dimers.
doi:10.1107/S1600536808012300
PMCID: PMC2961788  PMID: 21202864
2.  1-(4-Methyl­benzo­yl)-3-{2-[3-(4-methyl­benzo­yl)thio­ureido]phen­yl}thio­urea 
In the title compound, C24H22N4O2S2, the dihedral angles formed by the thio­ureido groups with the attached benzene ring are 43.81 (13) and 75.25 (13)°. The dihedral angle between the thio­ureido groups is 85.48 (10)°. The mol­ecule is stabilized by intra­molecular N—H⋯S, N—H⋯O and C—H⋯S hydrogen bonds. In the crystal, molecules are linked by intermolecular N—H⋯S hydrogen bonds together with C—H⋯π inter­actions.
doi:10.1107/S1600536811035586
PMCID: PMC3201486  PMID: 22058744
3.  4-Methyl-N-(2-methyl­benzo­yl)benzene­sulfonamide 
In the title compound, C15H15NO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. Further, the conformation of the C=O bond is syn to the ortho-methyl group in the benzoyl ring. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 87.1 (1)° and that between the sulfonyl and the benzoyl benzene rings is 58.2 (1)°. In the crystal structure, mol­ecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536810019513
PMCID: PMC2979502  PMID: 21579562
4.  N-(3-Methyl­benzo­yl)-2-nitro­benzene­sulfonamide 
In the title compound, C14H12N2O5S, the conformation between the N—H group and the ortho-nitro group in the sulfonyl benzene ring is syn and that between the C=O and meta-methyl groups in the benzoyl ring is anti. The mol­ecule is twisted at the S—N bond with a torsion angle of 64.3 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 75.73 (7)° and that between the sulfonyl and benzoyl benzene rings is 89.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O(S) hydrogen bonds.
doi:10.1107/S160053681200164X
PMCID: PMC3275215  PMID: 22347071
5.  4-Chloro-N-(3-methyl­benzo­yl)benzene­sulfonamide monohydrate 
In the title compound, C14H12ClNO3S·H2O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 84.4 (2)°. In the crystal, every water mol­ecule forms four hydrogen bonds with three different mol­ecules of 4-chloro-N-(3-methyl­benzo­yl)benzene­sulfonamide. One of the water H atoms forms a bifurcated hydrogen bond with both the sulfonyl and the carbonyl O atoms of the same mol­ecule. Mol­ecules are linked into layers in the ab plane through N—H⋯O and O—H⋯O hydrogen bonds.
doi:10.1107/S1600536811051932
PMCID: PMC3254406  PMID: 22259549
6.  2-Methyl-N-(4-methyl­benzo­yl)benzene­sulfonamide 
The asymmetric unit of the title compound, C15H15NO3S, contains two independent mol­ecules. The conformations of the N—C bonds in the C—SO2—NH—C(O) segments have gauche torsions with respect to the SO bonds. Further, the mol­ecules are twisted at the S atoms with torsion angles of −53.1 (2) and 61.2 (2)° in the two mol­ecules. The dihedral angles between the sulfonyl benzene rings and the —SO2—NH—C—O segments are 86.0 (1) and 87.9 (1)°. Furthermore, the dihedral angles between the sulfonyl and the benzoyl benzene rings are 88.1 (1) and 83.5 (1)° in the two mol­ecules. In the crystal, mol­ecules are linked by N—H⋯O(S) hydrogen bonds.
doi:10.1107/S1600536810007440
PMCID: PMC2984015  PMID: 21580592
7.  Crystal structure of 1-ferrocenyl-2-(4-methyl­benzo­yl)spiro­[11H-pyrrolidizine-3,11′-indeno[1,2-b]quinoxaline] 
In the title compound the four-fused-rings system is approximately planar and the pyrrolidine rings of the pyrrolidizine fragment adopt a twist conformation. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and C—H⋯π inter­actions, forming double-chains parallel to the c axis.
In the title compound, [Fe(C5H5)(C34H28N3O)], the four-fused-rings system of the 11H-indeno­[1,2-b]quinoxaline unit is approximately planar [maximum deviation = 0.167 (4) Å] and forms a dihedral angle of 37.25 (6)° with the plane of the benzene ring of the methyl­benzoyl group. Both pyrrolidine rings adopt a twist conformation. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and weak C—H⋯π inter­actions, forming double chains extending parallel to the c axis.
doi:10.1107/S1600536814017644
PMCID: PMC4186081  PMID: 25309158
crystal structure; ferrocen­yl; pyrrolidizine; quinoxaline; hydrogen bonds
8.  N-(4-Methyl­benzo­yl)-2-nitro­benzene­sulfonamide 
The asymmetric unit of the title compound, C14H12N2O5S, contains two independent mol­ecules. The dihedral angles between the aromatic rings are 82.03 (9) and 79.47 (8)° in the two independent mol­ecules. In the crystal, the two mol­ecules in the asymmetric unit are linked into dimers via pairs of N—H⋯O(S) hydrogen bonds to generate C(4) chains.
doi:10.1107/S1600536812003522
PMCID: PMC3297299  PMID: 22412489
9.  4-Chloro-N-(4-methyl­benzo­yl)benzene­sulfonamide 
In the title compound, C14H12ClNO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The mol­ecule is twisted at the S atom with a torsion angle of 69.0 (2)°. The dihedral angle between the sulfonyl benzene ring and the —SO2—NH—C—O segment is 77.2 (1)° and that between the sulfonyl and the benzoyl benzene rings is 89.5 (1)°. In the structure, mol­ecules are linked into chains via N—H⋯O hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536810019501
PMCID: PMC2979638  PMID: 21579561
10.  4-Chloro-N-(2-methyl­benzo­yl)benzene­sulfonamide 
In the title compound, C14H12ClNO3S, the conformation of the N—H bond in the C—SO2—NH—C(O) segment is anti to the C=O bond. The two aromatic rings are tilted relative to each other by 57.7 (1)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O(S) hydrogen bonds, forming centrosymmetric dimers.
doi:10.1107/S1600536810050087
PMCID: PMC3050156  PMID: 21522718
11.  2-Methyl-N-(2-methyl­benzo­yl)benzene­sulfonamide 
In the title compound, C15H15NO3S, the 2-methyl­phenyl ring bonded to the sulfonyl group is disordered with site-occupation factors of 0.75:0.25. The dihedral angles between the two aromatic rings are 67.6 (1) and 69.2 (1)° for the major and the minor occupied sites, respectively. In the crystal, mol­ecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds.
doi:10.1107/S1600536810026735
PMCID: PMC3007270  PMID: 21588306
12.  N-(3-Methyl­benzo­yl)benzene­sulfonamide 
The asymmetric unit of the title compound, C14H13NO3S, contains three independent mol­ecules in which the dihedral angles between the sulfonyl and benzoyl benzene rings are 83.3 (2), 84.4 (2) and 87.6 (2)°. In the crystal, mol­ecules are linked into chains running along the a axis via N—H⋯O hydrogen bonds.
doi:10.1107/S1600536812013931
PMCID: PMC3344466  PMID: 22590228
13.  Ethyl 2-[6-(4-methyl­benzo­yl)-7-phenyl-2,3-di­hydro-1H-pyrrolizin-5-yl]-2-oxo­acetate 
In the title compound, C25H23NO4, the pyrrolizine ring is approximately planar with an r.m.s deviation from planarity of 0.0053 Å, while the fused di­hydro­pyrrolizine ring adopts an envelope conformation with the C atom connected to two CH2 as the flap. The dihedral angles between the fused ring system and the phenyl and methyl­benzoyl rings are 41.65 (11) and 66.30 (8)°, respectively. In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions occur. One mol­ecule is linked to five adjacent ones through eight hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536813029401
PMCID: PMC3885017  PMID: 24454192
14.  tert-Butyl 2-methyl-2-(4-methyl­benzo­yl)propanoate 
The title compound, C16H22O3, is bent with a dihedral angle of 75.3 (1)° between the mean planes of the benzene ring and a group encompassing the ester functionality (O=C—O—C). In the crystal, the mol­ecules are linked into infinite chains held together by weak C—H⋯O hydrogen-bonded inter­actions between an H atom on the benzene ring of one mol­ecule and an O atom on the ketone functionality of an adjacent mol­ecule. The chains are arranged with neighbouring tert-butyl and dimethyl groups on adjacent chains exhibiting hydro­phobic stacking, with short C—H⋯H—C contacts (2.37 Å) between adjacent chains
doi:10.1107/S1600536810003144
PMCID: PMC2979969  PMID: 21579897
15.  4-Bromo-N-(di-n-propyl­carbamothioyl)­benzamide 
The synthesis of the title compound, C14H19BrN2OS, involves the reaction of 4-bromo­benzoyl chloride with potassium thio­cyanate in acetone followed by condensation of the resulting 4-bromo­benzoyl isothio­cyanate with di-n-propyl­amine. Typical thio­urea carbonyl and thio­carbonyl double bonds, as well as shortened C—N bonds, are observed in the title compound. The short C—N bond lengths in the centre of the mol­ecule reveal the effects of resonance in this part of the mol­ecule. The asymmetric unit of the title compound contains two crystallographically independent mol­ecules, A and B. There is very little difference between the bond lengths and angles of these mol­ecules. In mol­ecule B, one di-n-propyl group is twisted in a −anti­periplanar conformation with C—C—C—H = −179.1 (3)° and the other adopts a −synclinal conformation with C—C—C—H = −56.7 (4)°; in mol­ecule A the two di-n-propyl groups are twisted in + and −anti­periplanar conformations, with C—C—C—H = −179.9 (3) and 178.2 (3)°, respectively. In the crystal, the mol­ecules are linked into dimeric pairs via pairs of N—H⋯S hydrogen bonds.
doi:10.1107/S1600536809003511
PMCID: PMC2968555  PMID: 21582125
16.  Crystal structures of trans-di­chlorido­tetra­kis­[1-(2,6-diiso­propyl­phen­yl)-1H-imidazole-κN 3]iron(II), trans-di­bromido­tetra­kis­[1-(2,6-diiso­propyl­phen­yl)-1H-imidazole-κN 3]iron(II) and trans-di­bromido­tetra­kis­[1-(2,6-diiso­propyl­phen­yl)-1H-imidazole-κN 3]iron(II) diethyl ether disolvate1  
The title compounds are iron(II) dihalide complexes of the bulky arylimidazole ligand 1-(2,6-diisopropylphenyl)-1H-imidazole. The FeCl2 and FeBr2 complexes are isotypic, while the third compound, also an FeBr2 complex, crystallizes as a diethyl ether disolvate.
The title compounds, [FeCl2(C15H20N2)4], (I), [FeBr2(C15H20N2)4], (II), and [FeBr2(C15H20N2)4]·2C4H10O, (IIb), respectively, all have triclinic symmetry, with (I) and (II) being isotypic. The FeII atoms in each of the structures are located on an inversion center. They have octa­hedral FeX 2N4 (X = Cl and Br, respectively) coordination spheres with the FeII atom coordinated by two halide ions in a trans arrangement and by the tertiary N atom of four aryl­imidazole ligands [1-(2,6-diiso­propyl­phen­yl)-1H-imidazole] in the equatorial plane. In the two independent ligands, the benzene and imidazole rings are almost normal to one another, with dihedral angles of 88.19 (15) and 79.26 (14)° in (I), 87.0 (3) and 79.2 (3)° in (II), and 84.71 (11) and 80.58 (13)° in (IIb). The imidazole rings of the two independent ligand mol­ecules are inclined to one another by 70.04 (15), 69.3 (3) and 61.55 (12)° in (I), (II) and (IIb), respectively, while the benzene rings are inclined to one another by 82.83 (13), 83.0 (2) and 88.16 (12)°, respectively. The various dihedral angles involving (IIb) differ slightly from those in (I) and (II), probably due to the close proximity of the diethyl ether solvent mol­ecule. There are a number of C—H⋯halide hydrogen bonds in each mol­ecule involving the CH groups of the imidazole units. In the structures of compounds (I) and (II), mol­ecules are linked via pairs of C—H⋯halogen hydrogen bonds, forming chains along the a axis that enclose R 2 2(12) ring motifs. The chains are linked by C—H⋯π inter­actions, forming sheets parallel to (001). In the structure of compound (IIb), mol­ecules are linked via pairs of C—H⋯halogen hydrogen bonds, forming chains along the b axis, and the diethyl ether solvent mol­ecules are attached to the chains via C—H⋯O hydrogen bonds. The chains are linked by C—H⋯π inter­actions, forming sheets parallel to (001). In (I) and (II), the methyl groups of an isopropyl group are disordered over two positions [occupancy ratio = 0.727 (13):0.273 (13) and 0.5:0.5, respectively]. In (IIb), one of the ethyl groups of the diethyl ether solvent mol­ecule is disordered over two positions (occupancy ratio = 0.5:0.5).
doi:10.1107/S1600536814014056
PMCID: PMC4158527  PMID: 25249858
aryl­imidazole; iron(II); crystal structure
17.  2-Methyl-N-(3-methyl­benzo­yl)benzene­sulfonamide 
In the title compound, C15H15NO3S, the sulfonyl and amide-bound benzene rings are oriented at dihedral angles of 83.1 (1) and 22.5 (3)°, respectively, with the almost planar S—N—C=O segment (r.m.s. deviation = 0.003 Å). The dihedral angle between the two benzene rings is 74.8 (1)°. In the crystal structure, pairs of mol­ecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds.
doi:10.1107/S1600536810002254
PMCID: PMC2979884  PMID: 21579848
18.  The cocrystal 2-hydr­oxy-4-methyl-N-propanoylbenzohydrazide–2-hydr­oxy-N-(2-hydr­oxy-4-methyl­benzo­yl)-6-methyl­benzohydrazide (2/1) 
The asymmetric unit of the title compound, 2C11H14N2O3·C16H16N2O4, contains one mol­ecule of 2-hydr­oxy-4-methyl-N-propanoylbenzohydrazide and one-half of a mol­ecule of 2-hydr­oxy-N-(2-hydr­oxy-4-methyl­benzo­yl)-6-methyl­benzohydrazide. The latter is located on a centre of inversion. Intra­molecular N—H⋯O inter­actions stabilize the conformations of both mol­ecules. The crystal structure is stabilized by inter­molecular N—H⋯O and O—H⋯O hydrogen bonds.
doi:10.1107/S1600536808033515
PMCID: PMC2959582  PMID: 21581004
19.  Crystal structure of 2,7-dieth­oxy-1,8-bis­(4-nitro­benzo­yl)naphthalene 
The title compound possesses crystallographically imposed twofold symmetry with two C atoms lying on the rotation axis and has a non-coplanarly accumulated aromatic-rings structure. In the crystal, C—H⋯O=C hydrogen bonds between the benzene rings and the carbonyl groups and C—H⋯O=N hydrogen bonds between the benzene rings and the nitro groups are observed; these C—H⋯O hydrogen bonds link the mol­ecules, forming a three-dimensional structure.
The title compound, C28H22N2O8, possesses crystallographically imposed twofold symmetry, with the two central carbon atoms of the naphthalene unit lying on the rotation axis. The two benzoyl groups in the mol­ecule are twisted away from the attached naphthalene unit with a C—C—C=O torsion angle of 49.05 (15)° between the naphthalene unit and the carbonyl group. The dihedral angle between the naphthalene ring system and the benzene ring is 77.17 (5)°. In the crystal, pairs of C—H⋯O=C hydrogen bonds link the mol­ecules into a double-column structure along the c axis. The mol­ecules are further linked by C—H⋯O=N hydrogen bonds, forming a three-dimensional network. C—H⋯π inter­actions between the methyl­ene group and the naphthalene unit and π–π inter­actions between the naphthalene ring systems [centroid–centroid distances of 3.7858 (7)–3.7860 (7) Å] are also observed.
doi:10.1107/S1600536814018674
PMCID: PMC4186128  PMID: 25309162
crystal structure; peri-aroyl­naphthalene; naphthalene diketone; non-coplanarly accumulated aromatic-rings structure; spatial organization
20.  2-(1H-Benzotriazol-1-yl)-1-(3-methyl­benzo­yl)ethyl benzoate 
In the title mol­ecule, C23H19N3O3, the dihedral angles between the mean plane of the benzotriazole ring system and the benzene and phenyl rings are 9.67 (9) and 86.08 (10)°, respectively. The dihedral angle between the benzene and phenyl rings is 85.89 (11)°. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains along [010].
doi:10.1107/S1600536809026853
PMCID: PMC2977413  PMID: 21583575
21.  1-(4-Methyl­benzo­yl)-3-[5-(4-pyrid­yl)-1,3,4-thia­diazol-2-yl]urea 
In the title compound, C16H13N5O2S, the five non-H atoms of the urea linkage adopt a planar configuration owing to the presence of an intra­molecular N—H⋯O hydrogen bond. The maximum deviation from planarity is 0.022 (2) Å. The thia­diazole and pyridine heterocyclic rings are close to being coplanar, with a dihedral angle of 6.7 (2)° between their mean planes. Inter­molecular N—H⋯O hydrogen bonds link two neighbouring mol­ecules into centrosymmetric R 2 2(8) dimers. Four C atoms and the attached H atoms of the benzene ring are disordered over two positions of equal occupancy.
doi:10.1107/S1600536808035149
PMCID: PMC2959837  PMID: 21581236
22.  4-Carbethoxy-1-[4-(N,N-dimethylamino)benzoyl]thiosemicarbazide 
The mol­ecular structure of the title compound, C13H18N4O3S, (systematic name: ethyl N-{2-[4-(dimethyl­amino)benzo­yl]hydrazinethio­carbon­yl}carbamate) is stabilized by intra­molecular N—H⋯O=C hydrogen bonding arranged in an S(6) graph-set motif. In the crystal, inversion dimers connected via inter­molecular N—H⋯S=C hydrogen bonds [R 2 2(8) graph-set motif] form sheets parallel to the (21) plane. Dimers are also formed by the mol­ecules via weak inter­molecular N—H⋯S=C hydrogen bonds [R 2 2(10) graph-set motif] connecting the sheets.
doi:10.1107/S1600536810015576
PMCID: PMC2979162  PMID: 21579260
23.  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
24.  N-(4-Methyl­benzo­yl)-4-nitro­benzene­sulfonamide 
In the title compound, C14H12N2O5S, the dihedral angle between the nitro­phenyl group and the –S—NH—C—O fragment is 80.74 (17)° and that between the nitro­phenyl and methyl­phenyl groups is 87.66 (14)°. The C—S—N—C torsion angle at the S—N bond is −67.0 (3)°. In the crystal, mol­ecules are linked into C(4) chains via N—H⋯O hydrogen bonds.
doi:10.1107/S1600536812007854
PMCID: PMC3297935  PMID: 22412738
25.  2-(4-Methyl­benzo­yl)benzoic acid monohydrate 
In the title compound, C15H12O3·H2O, the two rings are oriented at a dihedral angle of 69.12 (3)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional framework.
doi:10.1107/S1600536808010581
PMCID: PMC2961241  PMID: 21202377

Results 1-25 (306519)