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1.  Crystal Structure of Dimeric Flavodoxin from Desulfovibrio gigas Suggests a Potential Binding Region for the Electron-Transferring Partner 
Flavodoxins, which exist widely in microorganisms, have been found in various pathways with multiple physiological functions. The flavodoxin (Fld) containing the cofactor flavin mononucleotide (FMN) from sulfur-reducing bacteria Desulfovibrio gigas (D. gigas) is a short-chain enzyme that comprises 146 residues with a molecular mass of 15 kDa and plays important roles in the electron-transfer chain. To investigate its structure, we purified this Fld directly from anaerobically grown D. gigas cells. The crystal structure of Fld, determined at resolution 1.3 Å, is a dimer with two FMN packing in an orientation head to head at a distance of 17 Å, which generates a long and connected negatively charged region. Two loops, Thr59–Asp63 and Asp95–Tyr100, are located in the negatively charged region and between two FMN, and are structurally dynamic. An analysis of each monomer shows that the structure of Fld is in a semiquinone state; the positions of FMN and the surrounding residues in the active site deviate. The crystal structure of Fld from D. gigas agrees with a dimeric form in the solution state. The dimerization area, dynamic characteristics and structure variations between monomers enable us to identify a possible binding area for its functional partners.
doi:10.3390/ijms14011667
PMCID: PMC3565340  PMID: 23322018
flavodoxin (Fld); flavin mononucleotide (FMN); crystal structure; dimer; binding region
2.  (2E)-2-{[3-Methyl-5-(2-naphth­yloxy)-1-phenyl-1H-pyrazol-4-yl]methyl­idene}hydrazinecarbothio­amide monohydrate 
In the title compound, C22H19N5OS·H2O, the naphthalene ring system and the benzene ring [dihedral angle = 85.19 (8)°] make dihedral angles of 87.02 (9) and 14.41 (10)°, respectively, with the pyrazole ring. The mean plane through the 2-methyl­enehydrazinecarbothio­amide group [C—N—N—C(=S)—N; maximum deviation = 0.022 (1) Å] is slightly twisted from the pyrazole ring [dihedral angle = 5.60 (11)°]. In the crystal, mol­ecules are linked by N—H⋯S, N—H⋯O, O—H⋯S, O—H⋯N and C—H⋯S hydrogen bonds into sheets parallel to the ab plane. π–π inter­actions are also observed [centroid-to-centroid distances = 3.7778 (12) and 3.7010 (12) Å].
doi:10.1107/S1600536812039815
PMCID: PMC3470403  PMID: 23125816
3.  (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
4.  5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole 
In the title compound, C21H16BrFN2, the fluoro-substituted benzene ring is disordered over two orientations about the C—F bond and the C—C bond between the benzene and pyrazole groups with a site-occupancy ratio of 0.516 (8):0.484 (8). The central pyrazole ring [maximum deviation = 0.035 (3) Å] makes dihedral angles of 22.4 (2), 11.0 (2), 77.19 (16) and 7.44 (17)° with the two disorder components of the benzene ring, the bromo-substituted benzene ring and the phenyl ring, respectively. In the crystal, mol­ecules are linked into a layer parallel to the bc plane through C—H⋯π inter­actions.
doi:10.1107/S160053681203454X
PMCID: PMC3435702  PMID: 22969573
5.  N-[(4-Chloro­phen­yl)sulfon­yl]acetamide 
The asymmetric unit of the title compound, C8H8ClNO3S, consists of two crystallographically independent mol­ecules (A and B). The dihedral angles between the benzene ring and amide C—C(=O)—NH– plane are 87.6 (3) (mol­ecule A) and 86.0 (3)° (mol­ecule B). In the crystal, the independent mol­ecules are alternately linked by N—H⋯O hydrogen bonds into an infinite chain along the b axis. Short inter­molecular Cl⋯Cl contacts [3.2882 (5) and 3.2812 (5) Å] are also observed.
doi:10.1107/S1600536812033764
PMCID: PMC3435654  PMID: 22969527
6.  N-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)-4,4′′-difluoro-5′-hy­droxy-1,1′:3′,1′′-terphenyl-4′-carboxamide 
The asymmetric unit of the title compound, C27H16F2N2O4, consists of two crystallographically independent mol­ecules (A and B). In mol­ecule B, the isoindoline-1,3-dione ring system is disordered over two set of sites with a site-occupancy ratio of 0.658 (12):0.342 (12). In mol­ecule A, the fluoro-substituted benzene rings make dihedral angles of 18.36 (8) and 46.37 (8)° with the central benzene ring, whereas the corresponding angles are 40.90 (8) and 52.89 (9)° in mol­ecule B. The isoindoline ring system in mol­ecule A and the major and minor components of the disordered isoindoline ring system in mol­ecule B make dihedral angles of 58.50 (4), 54.13 (16) and 70.01 (28) °, respectively, with their attached benzene rings, linked through the amide group. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring in each mol­ecule. In the crystal, mol­ecules are linked by N—H⋯O, C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. The crystal studied was a non-merohedral twin with a refined twin component ratio of 0.9316 (8):0.0684 (8).
doi:10.1107/S160053681203365X
PMCID: PMC3435648  PMID: 22969521
7.  2,3,5-Triphenyl-2H-tetra­zol-3-ium iodide 
The asymmetric unit of the title mol­ecular salt, C19H15N4 +·I−, contains four 2,3,5-triphenyl-2H-tetra­zol-3-ium cations and five iodide anions, with two of the latter lying on crystallographic inversion centres. In each cation, the tetra­zole ring is essentially planar (r.m.s. deviations = 0.004–0.007 Å). The dihedral angles between the tetra­zole ring and its three attached benzene rings in the four independent cations are: 12.9 (4), 67.0 (4), 48.1 (4); 20.8 (4), 51.1 (4), 62.3 (4); 11.4 (4), 52.3 (4), 47.3 (4) and 6.0 (4), 85.7 (4), 43.5 (4)°. A C—H⋯I hydrogen bond and C—H⋯π inter­actions are observed in the crystal.
doi:10.1107/S1600536812033661
PMCID: PMC3435649  PMID: 22969522
8.  2,3,5-Triphenyl-2H-tetra­zol-3-ium bromide ethanol monosolvate 
In the title compound, C19H15N4 +·Br−·C2H5OH, the tetra­zole ring makes dihedral angles of 57.44 (9), 50.92 (9) and 4.65 (8)° with the attached phenyl rings. In the crystal, the cation and the anion are linked to each other by inter­molecular C—H⋯Br hydrogen bonds into an infinite chain along the b axis. The anion and the ethanol solvent mol­ecule are linked by an O—H⋯Br hydrogen bond. The crystal studied was an inversion twin with a refined component ratio of 0.632 (5):0.368 (5).
doi:10.1107/S1600536812032953
PMCID: PMC3415007  PMID: 22904994
9.  2,3,5-Triphenyl-2H-tetra­zol-3-ium tetra­phenyl­borate 
In the title salt, C19H15N4 +·C24H20B−, the tetra­phenyl­borate anion is in a tetra­hedral geometry around the B atom [C—B—C angles of 107.10 (9)–111.79 (9)°]. In the cation, the tetra­zole ring makes dihedral angles of 3.04 (7), 51.75 (7) and 51.13 (7)° with the attached phenyl rings. In the crystal, C—H⋯π inter­actions link the cations and anions into ion pairs.
doi:10.1107/S1600536812032941
PMCID: PMC3415008  PMID: 22904995
10.  (E)-2-(2,3-Dimethyl­anilino)-N′-(thio­phen-2-yl­methyl­idene)benzohydrazide 
In the title compound, C20H19N3OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9)° with the thio­phene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thio­phene ring and dimethyl-substituted benzene ring is 83.60 (9)°. The thio­phene ring and the benzene ring are twisted from the mean plane of the C(=O)—N—N=C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9) and 24.77 (8)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S160053681203259X
PMCID: PMC3414973  PMID: 22904960
11.  2-(2,3-Dimethyl­anilino)benzohydrazide 
In the title compound, C15H17N3O, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to coplanar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif in the mol­ecule, and a short intra­molecular contact (H⋯H = 1.88 Å) is also observed. In the crystal, mol­ecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S1600536812032576
PMCID: PMC3414975  PMID: 22904962
12.  2-Anilino-4-(1,3-benzothia­zol-2-yl)-5-(4-chloro­benzo­yl)thio­phene-3-carbonitrile 
In the title compound, C25H14ClN3OS2, the central thio­phene ring [maximum deviation = 0.011 (1) Å] makes dihedral angles of 55.72 (5), 13.36 (5) and 46.77 (4)° with the adjacent chloro-substituted benzene ring, the benzene ring and the 1,3-benzothia­zole ring system [maximum deviation = 0.012 (1) Å], respectively. An intra­molecular C—H⋯S(thienyl) hydrogen bond generates an S(6) ring motif in the mol­ecule. In the crystal, mol­ecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers and the dimers are further connected by C—H⋯O hydrogen bonds into tapes running along [100]. Aromatic π–π stacking inter­actions are also observed [centroid-to-centroid distances = 3.6116 (6) and 3.7081 (6) Å].
doi:10.1107/S1600536812032588
PMCID: PMC3414976  PMID: 22904963
13.  (N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chloro­phen­yl)ethane-1,2-diyl­idene]bis­(3-methyl-1-benzofuran-2-carbohydrazide) 
In the title compound, C28H21ClN4O4, the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C—N—N=C and C—N—N=C—C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intra­molecular N—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯(O,N) and C—H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C—H⋯O hydrogen bond into a sheet parallel to the bc plane. π–π inter­actions [centroid-to-centroid distances = 3.4845 (12)–3.6250 (13) Å] are also observed.
doi:10.1107/S1600536812030504
PMCID: PMC3414328  PMID: 22904861
14.  3-(3-Meth­oxy­phen­yl)benzo[d]thia­zolo[3,2-a]imidazol-9-ium hydrogen sulfate 
In the title mol­ecular salt, C16H13N2OS+·HSO4 −, the thia­zolo[3,2-a]benzimidazolium ring system is roughly planar [maximum deviation = 0.046 (3) Å] and makes a dihedral angle of 58.22 (11)° with the benzene ring. The meth­oxy group is almost coplanar with its attached benzene ring [Cmeth­yl—O—C—C = −1.6 (5)°]. In the crystal, the cation is linked to the anion by a bifurcated N—H⋯(O,O) hydrogen bond, generating an R 1 2(4) ring motif. The ion pairs are then connected by a C—H⋯O hydrogen bond into inversion dimers and these dimers are further linked by O—H⋯O hydrogen bonds into an infinite tape along [100]. A π–π stacking inter­action [centroid-to-centroid distance = 3.5738 (18) Å] and a short inter­molecular contact [S⋯O = 2.830 (3) Å] are also observed.
doi:10.1107/S1600536812030541
PMCID: PMC3414329  PMID: 22904862
15.  (Z)-1-(4-Methyl­phen­yl)-2-(phenyl­sulfon­yl)ethanone oxime 
The mol­ecule of the title compound, C15H15NO3S, has a twisted U-shaped conformation: the twist occurs at the central C—S(=O)2—C—C—C unit and the benzene ring makes a dihedral angle of 28.74 (7)° with the phenyl ring. The S—C—C=N torsion angle is −88.95 (13)°. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R 2 2(6) loops, and C—H⋯O hydrogen bonds connect the dimers into a three-dimensional network.
doi:10.1107/S1600536812030346
PMCID: PMC3414300  PMID: 22904833
16.  2-{2-[(E)-(2-Benzoyl­hydrazin-1-yl­idene)meth­yl]phen­oxy}acetic acid 
In the title compound, C16H14N2O4, the dihedral angle between the aromatic rings is 12.45 (6)°. The central C(=O)—N—N=C bridge is roughly planar (r.m.s. deviation = 0.0346 Å) and makes dihedral angles of 13.01 (7) and 0.56 (7)° with the attached phenyl and benzene rings, respectively. The acetic acid unit (r.m.s. deviation = 0.0066 Å) is twisted from its attached benzene ring [dihedral angle = 19.48 (6)°]. In the crystal, mol­ecules are linked by O—H⋯(O,N), N—H⋯O and C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. A weak aromatic π–π stacking inter­action is also observed [centroid–centroid distance = 3.7330 (7) Å].
doi:10.1107/S1600536812028735
PMCID: PMC3394044  PMID: 22798909
17.  2-[(1H-Benzimidazol-2-yl)sulfan­yl]-1-phenyl­ethanone 
The title compound, C15H12N2OS, adopts a twisted V-shape, with the S atom as the pivot. The benzimidazole ring system [maximum deviation = 0.015 (1) Å] makes a dihedral angle of 78.56 (7)° with the phenyl ring. The O atom of the ketone group is close to coplanar with its adjacent ring [O—C—C—C torsion angle = 11.0 (2)°]. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds into an infinite chain along [001]. The crystal packing also features a C—H⋯π inter­action.
doi:10.1107/S1600536812028747
PMCID: PMC3394045  PMID: 22798910
18.  1-Chloro-1-[(Z)-2-phenyl­hydrazin-1-yl­idene]propan-2-one 
The title compound, C9H9ClN2O, is close to planar (r.m.s. deviation for the non-H atoms = 0.0446 Å); it exists in a cis conformation with respect to the C=N double bond. In the crystal, the ketone O atom accepts both N—H⋯O and C—H⋯O hydrogen bonds, which leads to [010] infinite chains incorporating R 2 1(6) loops. The crystal structure also features a C—H⋯π inter­action.
doi:10.1107/S1600536812028759
PMCID: PMC3394046  PMID: 22798911
19.  (2E)-3-(6-Meth­oxy­naphthalen-2-yl)-1-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one 
The asymmetric unit of the title compound, C21H18O2S, consists of two crystallographically independent mol­ecules (A and B). The mol­ecules exist in a trans conformation with respect to the central C=C bond. The naphthalene ring system makes dihedral angles of 51.62 (12) (mol­ecule A) and 52.69 (12)° (mol­ecule B) with the benzene ring. In mol­ecule A, the prop-2-en-1-one group forms dihedral angles of 22.84 (15) and 29.02 (12)° with the adjacent naphthalene ring system and benzene ring, respectively, whereas the corresponding angles are 30.04 (12) and 23.33 (12)° in mol­ecule B. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds into head-to-tail chains along the a axis. The crystal packing also features C—H⋯π inter­actions. The crystal studied was a pseudo-merohedral twin with twin law (100 0-10 00-1) and a refined component ratio of 0.6103 (16):0.3897 (16).
doi:10.1107/S1600536812028930
PMCID: PMC3394057  PMID: 22798922
20.  4-Bromo­acetyl-3-phenyl­sydnone 
In the title compound (systematic name: 4-bromoacetyl-1,2,3-oxadiazol-3-ylium-5-olate), C10H7BrN2O3, the 1,2,3-oxadiazole ring and bromo­acetyl group are essentially planar [maximum deviation = 0.010 (4) and 0.013 (3) Å respectively] and form dihedral angles of 59.31 (19) and 67.96 (11)°, respectively, with the phenyl ring. The 1,2,3-oxadiazole ring is twisted slightly from the mean plane of the bromo­acetyl group, forming a dihedral angle of 9.16 (24)°. In the crystal, mol­ecules are linked by pairs of weak C—H⋯O hydrogen bonds into inversion dimers with R 2 2(12) ring motifs. The dimers are further connected by weak C—H⋯O hydrogen bonds into an infinite tape parallel to the b axis. In addition, π–π stacking inter­actions [centroid–centroid distance = 3.6569 (19) Å] and short inter­molecular contacts [O⋯O = 2.827 (3) and C⋯C = 3.088 (5) Å] are observed.
doi:10.1107/S1600536812026049
PMCID: PMC3393916  PMID: 22798781
21.  Ethyl 2-amino-4,5-dimethyl­thio­phene-3-carboxyl­ate 
In the title compound, C9H13NO2S, the mean planes of thio­phene ring [maximum deviation = 0.0042 (10) Å] and eth­oxy­carbonyl group [0.0242 (15) Å] are almost coplanar [dihedral angle between them = 0.68 (11)°]. The H atoms of the two methyl groups attached to the thio­phene ring are each disordered over two orientations with site-occupancy ratios of 0.77 (4):0.23 (4) and 0.84 (4):0.16 (4). An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into an infinite wave-like chain running parallel to the b-axis direction. The crystal structure also features C—H⋯π inter­actions.
doi:10.1107/S1600536812026268
PMCID: PMC3393923  PMID: 22798788
22.  N-[(4-Methyl­phen­yl)sulfon­yl]acetamide 
In the title compound, C9H11NO3S, the dihedral angle between the benzene ring and the amide group is 76.7 (3)°. In the crystal, mol­ecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers with R 2 2(8) ring motifs. The dimers are further connected by N—H⋯O and C—H⋯O hydrogen bonds into an infinite tape running parallel to the b-axis direction.
doi:10.1107/S1600536812024658
PMCID: PMC3393294  PMID: 22807851
23.  2-Amino-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile 
In the title mol­ecule, C21H15FN2O2, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109 (2) Å] is 83.35 (7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The meth­oxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −4.3 (3)°]. In the crystal, mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by π–π inter­actions [centroid–centroid distance = 3.7713 (9) Å].
doi:10.1107/S1600536812023021
PMCID: PMC3379488  PMID: 22719686
24.  Methyl 2-{6-[(1-meth­oxy-1-oxopropan-2-yl)amino­carbon­yl]pyridine-2-carboxamido}­propano­ate 
In the title compound, C15H19N3O6, the amide planes are inclined at dihedral angles of 0.8 (6) and 12.1 (3)° with respect to the central pyridine ring. The mean planes of the corresponding methyl acetate groups form dihedral angles of 41.76 (13) and 86.48 (15)°, respectively with the mean plane of pyridine ring. A pair of weak intra­molecular N—H⋯N hydrogen bonds generate an S(5)S(5) ring motif in the mol­ecule. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into [001] chains. The chains are cross-linked by C—H⋯O hydrogen bonds into layers lying parallel to bc plane. The crystal packing also features a C—H⋯π inter­action.
doi:10.1107/S1600536812022258
PMCID: PMC3379408  PMID: 22719606
25.  Ethyl 2-amino-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate 
In the title compound, C23H20FNO4, the fluoro-substituted benzene ring is approximately perpendicular to the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.264 (1) Å], with a dihedral angle of 83.79 (6)°. The pyran ring adopts a flattened boat conformation. The meth­oxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −2.1 (2)°]. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯F hydrogen bonds into a layer parallel to the bc plane. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S1600536812021939
PMCID: PMC3379378  PMID: 22719576

Results 1-25 (53)