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1.  4′-(4-Fluoro­phen­yl)-1′-methyl­dispiro­[indane-2,2′-pyrrolidine-3′,2′′-indane]-1,3,1′′-trione methanol hemisolvate 
The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent mol­ecules and a one methanol solvent mol­ecule. The methanol mol­ecule is O—H⋯O hydrogen bonded to one of the independent mol­ecules. The pyrrolidine rings in both mol­ecules adopt half-chair conformations, while the cyclo­pentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent mol­ecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one mol­ecule, and 72.78 (8) and 77.27 (8)° in the other. In each mol­ecule, a weak intra­molecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯F hydrogen bonds link the mol­ecules into a three-dimensional network.
doi:10.1107/S1600536813009987
PMCID: PMC3648276  PMID: 23723896
2.  4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C30H22BrNO2, the cyclo­pentane ring of the dihydro­acenaphthyl­ene group and the pyrrolidine ring are both in envelope conformations with the spiro C atom and N atom, respectively, as the flap atom. The cyclo­pentane ring of the indane group adopts a half-chair conformation. A weak intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring of the bromo­phenyl group and the benzene ring of the indane group, respectively. The dihedral angle between the two benzene rings is 83.92 (7)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. Weak C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812014213
PMCID: PMC3344476  PMID: 22590238
3.  4′-(3-Bromo­phen­yl)-1′-methyl­dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione 
In the title compound, C27H20BrNO3, two intra­molecular C—H⋯O hydrogen bonds both form S(6) rings. The pyrrolidine ring adopts a twisted conformation about the C—C bond bearing the indane ring systems. The other two five-membered rings within the indane systems are in shallow envelope conformations, with the spiro C atoms as the flap atoms. The mean plane of the pyrrolidine ring [maximum deviation = 0.275 (1) Å] makes dihedral angles of 65.25 (7), 78.33 (6) and 75.25 (6)° with the bromo-substituted benzene ring and the mean planes of the mono- and dioxo-substituted indane rings, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. In addition, C—H⋯π inter­actions are observed.
doi:10.1107/S1600536812037993
PMCID: PMC3470256  PMID: 23125700
4.  4′-[5-(4-Fluoro­phen­yl)pyridin-3-yl]-1′-methyl­dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione 
In the title compound, C32H23FN2O3, the pyrrolidine ring adopts an envelope conformation. The monoketo- and diketo-substituted five-membered rings are in envelope and half-chair conformations, respectively. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked via inter­molecular C—H⋯N and C—H⋯O hydrogen bonds into a three-dimensional network. The crystal structure is further consolidated by C—H⋯π inter­actions.
doi:10.1107/S1600536811032946
PMCID: PMC3200886  PMID: 22058982
5.  4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione 
In the title compound, C27H20BrNO3, the pyrrolidine ring adopts a half-chair conformation, while the other five-membered rings adopt flattened envelope conformations with the spiro C atoms as the flap atoms. An intra­molecular C—H⋯O hydrogen bond occurs, generating an S(6) ring. In the crystal, mol­ecules are connected via weak C—H⋯O hydrogen bonds, forming chains along the c axis.
doi:10.1107/S1600536811044515
PMCID: PMC3247508  PMID: 22220126
6.  7′-[4-(Trifluoro­meth­yl)phen­yl]-5′,6′,7′,7a’-tetra­hydrodispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
In the title compound, C29H20F3NO3S, the thia­zolidine ringadopts a half-chair conformation. The pyrrolidine and two five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. The trifluoro­methyl-substituted benzene ring forms dihedral angles of 62.37 (14) and 87.40 (14)° with the benzene rings of the dihydro-1H-indene units. The two benzene rings form a dihedral angle of 36.94 (15)°. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol­ecules are linked into inversion dimers by pairs of inter­molecular C—H⋯O hydrogen bonds, generating R 2 2(10) ring motifs.
doi:10.1107/S1600536811047118
PMCID: PMC3238947  PMID: 22199796
7.  7′-Phenyl-5′,6′,7′,7a′-tetra­hydro­dipiro[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
The asymmetric unit of the title compound, C28H21NO3S, contains two mol­ecules with similar geometries. The thia­zolidine rings adopt half-chair conformations while the pyrrolidine and the diketo-substituted five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. In one mol­ecule, the phenyl ring forms dihedral angles of 57.76 (12) and 71.79 (12)° with the fused benzene rings and the fused benzene rings form a dihedral angle of 57.75 (13)°. The corresponding dihedral angles in the other mol­ecule are 60.04 (12), 72.93 (12) and 54.51 (13)°. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol­ecules are linked via C—H⋯O and C—H⋯N hydrogen bonds into layers lying parallel to the ab plane.
doi:10.1107/S1600536811046174
PMCID: PMC3238881  PMID: 22199734
8.  1′-Methyl-4′-(1-naphth­yl)-1′′,2′′,3′′,4′′-tetra­hydro­indane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione 
In the title compound, C32H25NO3, the pyrrolidine ring adopts an envelope conformation, whereas the cyclo­hexa­none ring in the tetra­hydro­naphthalene fused-ring system adopts a half-chair conformation. The indanedione unit is oriented at an angle of 58.9 (1)° with respect to the naphthyl ring system. Three intra­molecular C—H⋯O close contacts and an intra­molecular C—H⋯π inter­action are observed. In the crystal, mol­ecules associate via C—H⋯O hydrogen bonds, forming a helical chain with a C(10) motif along the b axis.
doi:10.1107/S1600536811004880
PMCID: PMC3052033  PMID: 21522383
9.  7′-Phenyl-1′,3′,5′,6′,7′,7a’-hexa­hydro­dipiro[acenaphthyl­ene-1,5′-pyrrolo­[1,2-c]thia­zole-6′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C31H23NO2S, the pyrrolidine ring adopts an envelope conformation (with the spiro C atom as the flap), while the thia­zolidine ring and the two cyclo­pentane rings adopt twisted conformations. The mean plane through the hexa­hydro­pyrrolo­[1,2-c]thia­zole ring [r.m.s deviation = 0.400 (1) Å] forms dihedral angles of 76.83 (4), 80.70 (5) and 79.00 (4)° with the benzene ring and the mean planes of the dihydro­acenaphthyl­ene and the dihydro­indene rings, respectively. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. One of the ketone O atoms accepts three such bonds. Weak C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812013293
PMCID: PMC3344191  PMID: 22606194
10.  1′-Methyl-4′-[4-(trifluoro­meth­yl)phen­yl]dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C31H22F3NO2, the pyrrolidine and cyclo­pentane rings within the dihydro­indene ring system are in envelope conformations, with the N atom and the spiro-C atom at the flap, respectively. An intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The mean plane through the pyrrolidine ring [r.m.s. deviation = 0.179 (2) Å] makes dihedral angles of 86.30 (13), 88.99 (10) and 79.69 (11)° with the benzene ring, the dihydro­acenaphthyl­ene ring and the mean plane of the indane system, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. C—H⋯π inter­actions further stabilize the crystal structure.
doi:10.1107/S1600536812013645
PMCID: PMC3344443  PMID: 22590205
11.  1′-Methyl-4′-[4-(trifluoro­meth­yl)phen­yl]dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione 
In the title compound, C28H20F3NO3, the pyrrolidine ring adopts a half-chair conformation. The other five-membered rings adopt envelope conformations with the spiro and methylene C atoms as the flap atoms. In the crystal, mol­ecules are connected via weak C—H⋯O hydrogen bonds, forming sheets parallel to the bc plane.
doi:10.1107/S1600536811044527
PMCID: PMC3247509  PMID: 22220127
12.  7′-(4-Bromo­phen­yl)-5′,6′,7′,7a’-tetra­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
In the title compound, C28H20BrNO3S, the thia­zolidine, pyrrolidine and two five-membered carbocyclic rings are in envelope conformations. The bromo-bound phenyl ring forms dihedral angles of 61.97 (18) and 88.30 (17)° with the other two benzene rings. The two benzene rings form a dihedral angle of 30.3 (2)°. The mol­ecular structure features an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811046514
PMCID: PMC3238931  PMID: 22199780
13.  5,6-Dimeth­oxy-4′,5′-diphenyl­indane-2-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-1,2′′-dione 
In the title compound, C33H28N2O4, the central pyrrolidine ring adopts a half-chair conformation. Both the indolinone and indanone groups are twisted, with their five-membered rings adopting a half-chair and an envelope conformation, respectively. The two benzene rings and the mean plane of the indolinone and indanone groups make dihedral angles of 71.98 (10), 84.32 (10), 86.26 (9) and 78.50 (9)°, respectively, with the central pyrrolidine ring. Intra­molecular C—H⋯O hydrogen bonds stabilize the mol­ecular conformation. In the crystal, pairs of inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers. The dimers are inter­connected into ribbons propagating along [110] via weak inter­molecular C—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯π and π–π [centroid–centroid distance = 3.6509 (11) Å] inter­actions are also observed.
doi:10.1107/S1600536810035865
PMCID: PMC2983396  PMID: 21587525
14.  (1S,3′S,3a′R,6′S)-6′-(2-Chloro­phen­yl)-3′-[(2R,3S)-1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetra­hydro-2H,2′H-spiro­[ace­naphthyl­ene-1,1′-pyrrolo­[1,2-c][1,3]thia­zole]-2′,2′-dicarbo­nitrile 
The mol­ecular conformation of the title compound, C41H29ClN4O3S, is stabilized by intra­molecular C—H⋯O and C—H⋯Cl hydrogen bonds. The thia­zole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N—C bond involving the spiro C atom. The β la­ctam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thia­zole and pyrrolidine rings, respectively. The thia­zole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclo­pentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclo­pentane ring. The O atom attached to the β la­ctam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclo­pentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains along [010], and C—H⋯π and π-π inter­actions [centroid-centroid distance = 3.6928 (17) Å].
doi:10.1107/S1600536813009276
PMCID: PMC3648279  PMID: 23723899
15.  1′-Methyl-4′-phenyldispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione 
The conformation of the title compound, C27H21NO3, is stabilized by a weak intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. The pyrrolidine ring adopts a half-chair conformation. Both of the other five-membered rings are in envelope conformations. No significant inter­molecular hydrogen bonds are observed.
doi:10.1107/S1600536811032934
PMCID: PMC3200932  PMID: 22064935
16.  5′-Amino-1,3-dioxo-2′,3′-di­hydro-7′H-spiro­[indane-2,7′-thieno[3,2-b]pyran]-6′-carbonitrile 1′,1′-dioxide 
The title compound, C16H10N2O5S, was synthesized via the condesation of dihydro­thio­phen-3(2H)-one 1,1-dioxide, 1H-indene-1,2,3-trione and malononitrile in ethanol. The 2,3-dihydro­thio­phene 1,1-dioxide and pyran rings adopt envelope conformations. The mean planes through the planar part of the pyran ring and the benzene ring are nearly perpendicular, forming a dihedral angle of 88.40 (7)°. The crystal packing is stabilized by inter­molecular N—H⋯O and N—H⋯N hydrogen bonds with the sulfone O atom and the cyano N atom acting as acceptors.
doi:10.1107/S1600536810010019
PMCID: PMC2983812  PMID: 21580720
17.  7′-(2,5-Dimeth­oxy­phen­yl)-1′,3′,5′,6′,7′,7a’-hexa­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
In the title compound, C30H25NO5S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intra­molecular C—H⋯O inter­actions stabilize the mol­ecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexa­hydro­pyrrolo­[1,2-c]thia­zole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Mol­ecules are linked by inter­molecular C—H⋯O inter­actions into a three-dimensional network. In addition, C—H⋯π and π–π inter­actions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.
doi:10.1107/S1600536812003169
PMCID: PMC3297291  PMID: 22412481
18.  2-[1′-(Benz­yloxy)spiro­[indane-1,2′-pyrrolidine]-5′-yl]aceto­nitrile 
In the title compound, C21H22N2O, the planes of the two six-membered rings make a dihedral angle of 89.51 (7)°. The pyrrolidine ring has a puckering amplitude q 2 = 0.418 (3) and a pseudo-rotation phase angle ϕ2 = −166.8 (5), adopting a twist conformation (T). The other five-membered ring has a puckering amplitude q 2 = 0.247 (2) and a pseudo-rotation phase angle ϕ2 = −173.7 (5), adopting an envelope conformation with the CH2 atom adjacent to the C atom common with the pyrrolidine ring as the flap. In the crystal, mol­ecules are linked via C—H⋯N, enclosing R 2 2(20) rings, forming chains propagating along [100]. The aceto­nitrile group is disordered over two positions and was refined with a fixed occupancy ratio of 0.56:0.44.
doi:10.1107/S1600536813017674
PMCID: PMC3793706  PMID: 24109293
19.  4′-Ferrocenyl-1′-methylacenapthylene-1-spiro-2′-pyrrolidine-3′-spiro-2′′-indane-2,1′′,3′′(1H)-trione 
In the title compound, [Fe(C5H5)(C29H20NO3)], the acenaphthyl­ene ring system makes a dihedral angle of 83.77 (3)° with the indane-1,3-dione ring system. The central pyrrolidine ring exhibits a twist conformation. In the crystal, mol­ecules are linked by a weak inter­molecular C—H⋯O inter­action into a chain along the b axis. Two weak intra­molecular C—H⋯O inter­actions are also present.
doi:10.1107/S1600536809049629
PMCID: PMC2972181  PMID: 21578681
20.  6-Amino-5-(1-amino-2,2-dicyano­vin­yl)-3,3a,4,5-tetra­hydro-2H-indene-4-spiro-1′-cyclo­pentane-3a,7-dicarbonitrile–thio­phene-2-carbaldehyde (1/0.5) 
In each of the two independent indene-4-spiro­pentane mol­ecules in the asymmetric unit of the title 2:1 adduct, C19H18N6·0.5C5H4OS, the cyclo­hexene ring adopts a half-chair conformation and the cyclo­pentene and cyclo­pentane rings adopt envelope conformations. The mean plane through the cyclo­hexene/cyclo­pentene fused system is aligned at a dihedral angle of 77.9 (1)° with respect to the mean plane through the cyclo­pentane ring in one mol­ecule and 87.0 (1)° in the other. In the crystal, adjacent indene-4-spiro­pentane mol­ecules are linked by N—H⋯N hydrogen bonds into a three-dimensional network. The spaces within the network are occupied by the thio­phene-2-carbaldehyde mol­ecules. The thio­phene-2-carbaldehyde unit is disordered over two positions of equal occupancy. The crystal studied was found to be a non-morohedral twin with two minor twin components of 18.4 and 9.7%.
doi:10.1107/S1600536810034434
PMCID: PMC2983394  PMID: 21587485
21.  6-Ferrocenoyl-7-phenyl­spiro­[hexa­hydro­pyrrolo­[1,2-c][1,3]thia­zole-5,11′-indeno­[1,2-b]quinoxaline] 
In the title compound, [Fe(C5H5)(C32H24N3OS)], both the thia­zolidine ring and the pyrrolidine ring adopt an envelope conformation, with the S atom and the phenyl-bearing C atom, respectively, as the flaps. The thia­zolidine ring mean plane makes a dihedral angle of 59.08 (11)° with the pyrrolidine ring mean plane, which in turn makes a dihedral angle of 83.40 (10)° with the cyclo­pentane ring, indicating that the latter two rings are almost orthogonal to one another. In the crystal, a pair of C—H⋯O hydrogen bonds link the mol­ecules forming inversion dimers. The dimers are linked via π–π inter­actions [centroid–centroid distance = 3.7764 (10) Å] involving the quinoxaline moieties forming chains propagating along [1-10].
doi:10.1107/S1600536813022605
PMCID: PMC3884422  PMID: 24426995
22.  2,5-Dibromo­indan-1-ol 
In the title compound, C9H8Br2O, the cyclo­pentene ring adopts an envelope conformation with the brominated C atom as the flap. In the crystal, mol­ecules are linked by strong O—H⋯O hydrogen bonds into zigzag C(4) chains along [010]. In addition, a C—H⋯π inter­action involving the benzene ring and the H atom attached to the hy­droxy­lated C atom is observed.
doi:10.1107/S1600536812035829
PMCID: PMC3435824  PMID: 22969670
23.  1′-Methyl-4′-(4-methyl­phen­yl)dispiro­[indane-2,3′-pyrrolidine-2′,3′′-indoline]-1,2′′-dione 
In the title mol­ecule, C27H24N2O2, the pyrrolidin-2-one ring is almost planar (r.m.s. deviation = 0.003 Å), the pyrrolidine ring has an envelope conformation (the N atom is the flap atom) and the cyclo­penta­none ring is twisted about the Cq—Cm bond (q = quaternary and m = methylene). The ketone O atoms are directed to opposite sides of the mol­ecule. Supra­molecular chains along the a axis are formed in the crystal packing mediated by N—H⋯N and C—H⋯O inter­actions. These are connected into layers in the ab plane via C—H⋯π inter­actions.
doi:10.1107/S1600536812028012
PMCID: PMC3393996  PMID: 22798861
24.  Triethyl­ammonium (indane-1,2,3-trione 1,2-dioximato-κ2 N 1,O 2)(indane-1,2,3-trione 2-oximato 1-oxime-κ2 N 1,O 2)nickel(II) 
In the title compound, (C6H16N)[Ni(C9H4N2O3)(C9H5N2O3)], the NiIIion is four-coordinated by two N atoms and two O atoms from two indane-1,2,3-trione-1,2-dioxime ligands. The two organic ligands are linked by an intra­molecular O—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by N—H⋯O hydrogen-bonds.
doi:10.1107/S1600536812010458
PMCID: PMC3343825  PMID: 22589799
25.  Ethyl 1′′-benzyl-2′′-oxo-2′,3′,5′,6′,7′,7a’-hexa­hydro-1′H-di­spiro­[indeno­[1,2-b]quinoxaline-11,2′-pyrrolizine-3′,3′′-indoline]-1′-carboxyl­ate monohydrate 
In the title compound, C38H32N4O3·H2O, the quinoxaline–indene and pyrrolizine systems are essentially planar, with maximum deviations from their mean planes of 0.162 and 0.563 Å, respectively. The pyrrolizine ring forms dihedral angles of 88.53 (5) and 89.95 (8)° with the quinoxaline–indene system and the indoline ring, respectively. The central pyrrolidine ring has an envelope conformation with the C atom bearing the quinoxaline-indene system as the flap. The pyrrolidine ring of the indole system adopts an envelope conformation with the C atom bonded to the pyrrolizine ring N atom as the flap. The five-membered ring attached to the central pyrolidine ring adopts a twisted conformation. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds between water mol­ecules and pyrrolizine N and carbonyl O atoms together with C—H⋯O inter­actions result in chains along [100].
doi:10.1107/S1600536813011537
PMCID: PMC3684937  PMID: 23795039

Results 1-25 (126749)