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1.  1-[3-(Naphthalen-1-yl)phen­yl]naphthal­ene1  
The title compound, C26H18, consists of a benzene ring with meta-substituted 1-naphthalene substituents, which are essentially planar (r.m.s. deviation = 0.039 and 0.027 Å). The conformation is mixed syn/anti, with equivalent torsion angles about the benzene–naphthalene bonds of 121.46 (11) and 51.58 (14)°.
PMCID: PMC3569826  PMID: 23424572
2.  2-[3-(Naphthalen-2-yl)phen­yl]naph­thal­ene1  
The title compound, C26H18, consists of a benzene ring with meta-substituted 2-naphthalene substituents, which are essentially planar [r.m.s. deviations = 0.022 (1) and 0.003 (1) Å]. The conformation is syn, with equivalent torsion angles about the benzene–naphthalene bonds of −36.04 (13) and +34.14 (13)°. The mol­ecule has quasi-C s mol­ecular symmetry.
PMCID: PMC3569827  PMID: 23424573
3.  5,7,8,10,11,13,14,16-Octa­hydro-6,15-(ethanoxyethanoxyethano)-1,4:17,20-dietheno[9,12,6,15]benzodioxadiaza­cyclo­docosine1  
The title compound, C32H40N2O4, is a 1,10-diaza-18-crown-6 cryptand with an o-terphenyl bridge. In the polyether ring, two adjacent –CH2– groups are disordered with very nearly equal populations of two conformers. The ordered bond lengths are normal, with average C—C = 1.511 (3) Å, C—O = 1.421 (3) Å, and C—N = 1.466 (4) Å. The r.m.s. deviations of the three rings of the terphenyl bridge vary from 0.007 to 0.009 Å and the two rings ortho to one another are twisted by 50.75 (5) and 47.76 (4)° with respect to the third ring. The N⋯N distance is 5.408 (1) Å.
PMCID: PMC3515318  PMID: 23284538
4.  Di-μ-carbonyl-bis­[bis­(triphenyl­phos­phane)rhodium(0)](Rh—Rh) acetone disolvate1  
The dirhodium complex, [Rh2(C18H15P)4(CO)2]·2(CH3)2CO, has crystallographic twofold symmetry and the Rh—Rh distance is 2.6266 (8) Å. The four atoms proximate to each Rh atom [Rh—P = 2.3222 (7) and 2.3283 (8) Å, and Rh—C = 1.961 (3) and 2.045 (3) Å] form a distorted tetra­hedron with large deviations from the putative tetra­hedral angles [r.m.s. deviation = 23 (1)°]. The six angles more closely approximate those of a trigonal bipyramid [r.m.s. deviation = 14 (1)°] with one missing equatorial ligand. The two bridging carbonyl ligands are much more linearly coordinated to one Rh [Rh—C O = 151.0 (2)°] than to the other [127.0 (2)°], and the two Rh2CO planes form a dihedral angle of 45.43 (5)°. The two acetone solvent mol­ecules are disordered, and their estimated scattering contribution was subtracted from the observed diffraction data using the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155].
PMCID: PMC3515148  PMID: 23284375
5.  (1E,2E)-1,2-Bis[(1-benzyloxymethyl-1H-indol-3-yl)methylidene]hydrazine 
The title compound, C34H30N4O2, lies on an inversion center and consists of two 3-substituted-1H-indole units linked by a 1,2-dimethyl­enehydrazine bridge. It is one of numerous examples in which two aromatic ring systems are joined by this 4-atom bridge. The geometry of the centrosymmetric bridge is: C(arom)—C = 1.444 (3), C=N = 1.284 (3), N—N = 1.414 (4) Å, C(arom)—C=N = 122.6 (2) and C=N—N = 111.9 (2)°. The nine non-H atoms of the indole unit lie in a plane (δr.m.s. = 0.0089 Å) which is twisted 6.0 (2)° with respect to the hydrazine bridge plane. The benzyl­oxymethyl substituents do not lie in the plane of the rest of the mol­ecule and are in a folded rather than an extended conformation. This is described by the three torsion angles in the middle of the C=N—C—O—CBz group, viz. 98.5 (3), −62.1 (3), and −66.3 (2)°.
PMCID: PMC3515253  PMID: 23284473
6.  1-(2-Hy­droxy-5-meth­oxy­phen­yl)-3-methyl­but-2-en-1-one1  
The title compound, C12H14O3, is a natural product derived from the medium-sized hawthorn Crataegus persimilis (’prunifolia’). The mean plane of the butene moiety is twisted by 13.27 (7)° with respect to the that of the dioxobenzaldehyde moiety. There is an intra­molecular hydrogen bond between the hydroxyl group and the carbonyl O atom.
PMCID: PMC3515231  PMID: 23284451
7.  Bis[2,3,4-trimethyl-5-[(3,4,5-trimethyl-2H-pyrrol-2-yl­idene-κN)meth­yl]-1H-pyrrolato-κN]copper(II)1  
In the title complex, [Cu(C15H19N2)2] or [Cu(L 2)] (HL is 3,3′,4,4′,5,5′-hexa­methyl­pyrromethene), the CuII atom is coordinated by four N atoms [Cu—N 1.939 (2)–1.976 (2) Å] from two L ligands in a distorted tetra­hedral geometry. The mean planes of the CuN2C3 metallocyclic rings form a dihedral angle of 72.73 (6)°. In the L ligands, the pyrrole rings are inclined to each other at dihedral angles of 3.03 (7) and 9.83 (7)°. The crystal packing exhibits weak inter­molecular C—H⋯π inter­actions, which form chains in [100].
PMCID: PMC3515100  PMID: 23284327
8.  μ2-m-Xylylenebis(salicylaldiminato)-bis­(η4-1,5-cyclo­octa­diene)dirhodium(I) dichloro­methane solvate 
In the title solvate, [Rh2(C22H18N2O2)(C8H12)2]·CH2Cl2, each organometallic mol­ecule is composed of two RhI cations, the tetra­dentate dianion α,α′-bis­(salicylaldiminato)-m-xylene and two 1,5-cyclo­octa­diene (COD) ligands. Each RhI atom is coordinated by one O atom [Rh—O = 2.044 (2) and 2.026 (2) Å], one N atom [Rh—N = 2.083 (2) and 2.090 (2) Å], and one COD ligand via two η2-bonds, each directed toward the mid-point of a C=C bond (Cg): Rh—Cg = 2.007 (2), 2.013 (2), 2.000 (2) and 2.021 (2) Å. Each RhI atom has a quasi-square-planar coordination geometry, with average r.m.s. deviations of 0.159 (1) and 0.204 (1) Å from the mean planes defined by Rh and the termini of its four coordinating bonds. The two COD ligands have quasi-C 2 symmetry, twisted from ideal C 2v symmetry by 30.0 (3) and −33.1 (3)°, and are quasi-enanti­omers of one another. The intra­molecular Rh⋯Rh distance of 5.9432 (3) Å suggests that there is no direct metal–metal inter­action.
PMCID: PMC3470182  PMID: 23125626
9.  N-[2-(Phenyl­sulfon­yl)eth­yl]benzyl­amine1  
The title compound, C15H17NO2S, exhibits intra­molecular hydrogen bonding between the amine H atom and a sulfonyl O atom. The conformation of the mol­ecule is described by the four PhCH2—NH—CH2—CH2—SO2Ph torsion angles of 79.6 (2), −166.21 (14), −70.29 (17) and −58.93 (13)°.
PMCID: PMC3470312  PMID: 23125725
10.  1,2-Bis{2-[2-(trimethyl­sil­yl)ethyn­yl]phen­yl}ethane-1,2-dione 
The title compound, C24H26O2Si2, has C 2 crystallographic symmetry. The dihedral angle between the aromatic rings is 84.5 (2)°. The acetyl­ene group is slightly non-linear, with angles at the acetyl­ene C atoms of 175.7 (2) and 177.0 (2)°. In the crystal structure, only van de Waals interactions occur.
PMCID: PMC3435835  PMID: 22969681
11.  Ortho­rhom­bic polymorph of (2E)-2-(2,3-dihydro-1H-inden-1-yl­idene)-2,3-di­hydro-1H-inden-1-one1  
The title compound, C18H14O, is polymorphic at 123 K. The ortho­rhom­bic form reported herein has two independent mol­ecules in the asymmetric unit, with mol­ecular volume 313.5 Å3. The previously reported triclinic (P-1) form [Raston & Scott (2000 ▶). Green Chem., 2, 49–52] has mol­ecular volume 309.6 Å3 at the same temperature. All three mol­ecules deviate significantly and systematically from the putative Cs symmetry (δr.m.s. = 0.0265, 0.0256, 0.0497 Å). Comparison of the two molecules in the orthorhombic polymorph shows that 16 of the 19 equivalent pairs of framework atoms have a mirror-image pattern of deviations (above/below plane), suggesting that the two are quasi-enanti­omorphs. The pattern of deviations in the triclinic form is nearly the same (13 of 19 atom pairs) as the ortho­rhom­bic form.
PMCID: PMC3435792  PMID: 22969638
12.  Monoclinic polymorph of 2,5-dide­oxy-2,5-epithio-1,3:4,6-bis-O-[(R)-phenyl­methyl­ene]-l-iditol1  
The title compound C20H20O4S, is polymorphic. In the tetra­gonal form, the mol­ecule lies on a crystallographic twofold axis, while the monoclinic form has only approximate C 2 mol­ecular symmetry. The greatest excursion from C 2 symmetry is in the orientation of the two phenyl rings; at 100 K, one of the rings is rotated −37.2 (3)° and the other by 46.9 (3)° from their symmetric (tetra­gonal) positions. There are only minor differences in the three-ring nucleus; the best mol­ecular fit of the tetra­gonal and monoclinic forms, both at 100 K and excluding phenyl rings and H atoms, shows an r.m.s. deviation of 0.066 Å. Both forms have the same absolute configuration.
PMCID: PMC3435692  PMID: 22969563
13.  (1R,4R,5aS,7S,9aS)-7,9a-Dimethyl-6-methyl­ene-3-oxo-1,3,4,5,5a,6,7,8,9,9a-deca­hydro­naphtho­[1,2-c]furan-1,4-diyl diacetate 
The title compound, C19H24O6, is a sesquiterpene lactone isolated from the Kenyan plant Warburgia ugandensis. Ring A adopts a chair conformation, ring B is in a C 2 twist conformation and the lactone ring is nearly planar with maximum deviation 0.007 (1) Å. The reported absolute configuration is based on that of the similar compound bromo-parasiticolide A and is supported by analysis of Bijvoet differences from light atoms in Mo Kα radiation.
PMCID: PMC3435643  PMID: 22969516
14.  1-(Adamantan-1-yl)-3-(4-meth­oxy­phenyl)prop-2-en-1-one1  
The title mol­ecule, C20H24O2, is a chalconoid derivative in which the keto–enone group is slightly distorted from planarity; the O=C—C=C torsion angle is 12.24 (13)°.
PMCID: PMC3414983  PMID: 22904970
15.  1,2,3,4,5,6,7,8,13,13,14,14-Dodeca­chloro-1,4,4a,4b,5,8,8a,12b-octa­hydro-1,4:5,8-dimethano­triphenyl­ene at 90 K1  
The previously reported room-temperature crystal structure [Jaud Baldy, Negrel, Poite & Chanon (1993 ▶). Z. Kristallogr. 204, 289–291] of the title compound, C20H8Cl12, is monoclinic with Z′ = 1, whereas the 90 K structure reported herein is triclinic with Z′ = 2 and shows a 2% volume contraction. The crystallographically independent unit chosen consists of both enanti­omers (Λ and Δ) of this propeller-like mol­ecule. Both enanti­omers display quasi-twofold symmetry, with average bond-length/bond-angle deviations of 0.0018 (4) Å and 0.41 (2)° for Λ, and 0.0026 (4) Å and 0.50 (2)° for Δ.
PMCID: PMC3414984  PMID: 22904971
16.  (S)-2-Oxotetra­hydro­furan-3-aminium bromide1  
In the title HBr salt of (S)-homoserine lactone, C4H8NO2 +·Br−, the five-membered ring has an envelope conformation, with the –CH2– C atom adjacent to the N-substituted C atom at the flap position. The four-atom mean plane (r.m.s. deviation = 0.005 Å) of the envelope forms a dihedral angle of 32.12 (9)° with the three-atom flap plane. The distorted square-pyramidal coordination about the anion involves five surrounding cations, with the square base defined by three N—H⋯Br hydrogen bonds [Br⋯N = 3.3046 (10), 3.3407 (12) and 3.3644 (13) Å] and near-contact with an H atom attached to C [Br⋯C = 3.739 (1) Å]. Another Br⋯C contact of 3.427 (1) Å defines the apex. There is also an N—H⋯O hydrogen bond present linking the cations.
PMCID: PMC3414985  PMID: 22904972
17.  Tetra­methyl anthracene-2,3,6,7-tetra­carboxyl­ate–tetra­methyl 9,10-dihydro-9,10-dioxoanthracene-2,3,6,7-tetra­carboxyl­ate (1/1)1  
In the title co-crystal, C22H16O10·C22H18O8, the independent tetra­methyl 9,10-dihydro-9,10-dioxoanthracene-2,3,6,7-tetra­carboxyl­ate, (I), and tetra­methyl anthracene-2,3,6,7-tetra­carboxyl­ate, (II), components occupy separate crystallographic inversion centers. In (II), the dihedral angles between the mean aromatic plane and the two independent carboxyl­ate planes are 41.32 (10) and −38.35 (10)°. The methyl­carboxyl­ate groups of (I) are disordered, with each resolvable into two groups. In the least disordered carboxyl­ate, the apparent angles between the mean aromatic plane and the two partial carboxyl­ate planes [site occupations = 0.510 (3) and 0.490 (3)] are 16.8 (3) and 23.3 (3)°. In the highly disordered group, the apparent angles between the mean aromatic plane and the two partial carboxyl­ate planes [site occupations = 0.510 (3) and 0.490 (3)] are 78.3 (3) and −74.1 (3)°. In addition, this extreme disorder leads to an artificially elongated C(aromatic)—C(carbox­yl) bond.
PMCID: PMC3414986  PMID: 22904973
18.  syn-5,10,15-Tris(dichloro­meth­yl)-5,10,15-trihy­droxy-5H-diindeno­[1,2-a:1′,2′-c]fluorene dichloro­methane 0.82-solvate 
The title compound, C30H18Cl6O3·0.82CH2Cl2, consists of a slightly cup-shaped seven-ring truxene nucleus with hy­droxy and dichloro­methyl substituents at stereocenters 5R/S, 10R/S and 15R/S. C—Cl distances are in the range 1.759 (4)–1.783 (3) Å. Solvent channels parallel to the b axis appear to be partially occupied by highly disordered dichloro­methane solvent mol­ecules, the contribution of which were removed from the refinement with the SQUEEZE procedure in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. Only one of the OH groups forms a hydrogen bond, which is inter­molecular to another OH group, forming centrosymmetric dimers in the crystal.
PMCID: PMC3379341  PMID: 22719539
19.  (2R,4R)-4-(2-Eth­oxy-2-oxoeth­yl)-2,6,6-trimeth­yl–2-oxo-1,3,6,2λ5-dioxaza­phospho­can-6-ium iodide 
The title compound, C11H23NO5P+·I−, consists of an eight-membered cationic heterocyclic ring in a boat–chair conformation. The ring features a tetra­alkyl­ammonium N and a methyl­phospho­nate P atom. A –CH2(CO)OC2H5 ester side chain at the C adjacent to oxygen produces two chiral centers at that substituted C atom and the P atom, both of which were determined to have absolute R,R configurations. A previously determined racemic bromide analog has exactly the same ring but with a –C15H31 side chain. In that structure, both chiral centers show the same relative R/S,R/S configurations, but the ring in the bromide analog is in a boat conformation.
PMCID: PMC3379206  PMID: 22719404
20.  25,26-Bis(propan-2-yl­idene)hepta­cyclo[,13.02,21.03,8.09,14.015,20]hexa­cosa-2(21),3,5,7,9(14),11,15,17,19,23-deca­ene 
In the title compound, C32H28, the central cyclo­octa­tetra­ene ring has a boat conformation, and the mol­ecule is saddle shaped. The seat is defined by the mean plane of the four-atom attachment points (r.m.s. deviation = 0.014 Å) of the two bicyclo­heptenyl substituents. These substituents comprise the pommel and cantle, with each mean plane defined by four atoms proximate to the seat (r.m.s. deviations = 0.002 and 0.004 Å). Relative to the seat, the pommel and cantle bend up 31.16 (4) and 29.40 (5)°, while the benzo units (flaps, r.m.s. deviations = 0.006 and 0.009 Å) bend down 36.75 (4) and 38.46 (4)°. The mean planes of the dimethyl­ethyl­idene units are almost perpendicular to the saddle seat, making dihedral angles 86.89 (4) and 88.01 (4)°.
PMCID: PMC3344665  PMID: 22590427
21.  (E)-3,3′,4,4′,7,7′,8,8′-Octa­methyl-2H,2′H-1,1′-bi(cyclo­penta­[fg]acenaphthyl­enyl­idene)-2,2′,5,5′,6,6′-hexa­one dichloro­methane monosolvate 
The title compound, C36H24O6·CH2Cl2, is a dimer of two essentially planar (r.m.s., deviations of fitted plane of 14 pyracene C atoms = 0.0539 and 0.0543 Å) tetra­cyclic pyracene frameworks (each with four methyl groups and three carbonyl groups on the peripheral carbon atoms) twisted along a central C=C bond with an angle of 50.78 (3)° at 90 K. There are notably long Csp 2—Csp 2 bonds associated with the carbonyl groups, the longest being 1.601 (3) Å between two carbonyl C atoms. There are also intermolecular carbonyl⋯carbonyl interactions of both parallel and antiparallel types, with C⋯O distances in the range 3.041 (3) to 3.431 (2) Å. This compound is of inter­est with respect to the synthesis of fullerene fragments, such as corannulene and semibuckminsterfullerene derivatives (or ‘buckybowls’), and is a side product of the previously reported oxidation reaction. Structural details, such as planarity analysis of fused rings, out-of-plane deviation of substituents, inter­molecular inter­actions, and longer than typical bond lengths, will be discussed as well as comparisons to structurally related compounds.
PMCID: PMC3344573  PMID: 22590335
22.  2,9,16,23-Tetra­kis(1-methyl­eth­yl)-5,6,11,12,13,14,19,20,25,26,27,28-dodecadehydro­tetra­benzo[a,e,k,o]cyclo­eicosene1  
The title compound, C48H40, is a tetra­isopropyl-substituted polyannulenoenyne. The unsubstituted polyannulenoenyne, C36H16 (CSD: RICVEE; CAS: 186494-87-1), has quasi-D 2 (222) symmetry, as determined by least-squares fit (excluding H atoms) to a model optimized in D 2 symmetry by mol­ecular mechanics (r.m.s. deviation = 0.239 Å). The least-squares fits of 36 common C atoms of the title compound (at 90 K) to the parent (at 295 K) and to the optimized model show r.m.s. deviations of 0.419 and 0.426 Å, respectively.
PMCID: PMC3239117  PMID: 22199965
23.  (5RS,10SR,15RS)-Trimethyl­truxene1  
The title mol­ecule, C30H24, was prepared as a possible precursor to buckminsterfullerene cages. The two enanti­omers adopt the anti configuration, with one S/R and two R/S methyl groups, one anti to the other two. The truxene framework is slightly non-planar: with respect to the central six-ring mean plane, the three methyl C atoms are 1.377 (3), −1.475 (3) and 1.515 (3) Å distant, whereas the respective proximate peripheral six-ring mean planes make dihedral angles of 6.27 (6), 3.45 (7) and −7.37 (7)°.
PMCID: PMC3239118  PMID: 22199966
24.  Dibenzo[a,e]penta­cyclo­[,9.02,13.05.10]octa­deca-2(13),5(10)-diene 
In the title compound, C26H24, the central cyclo­octa­tetra­ene ring has a boat conformation, and the mol­ecule is saddle shaped. The seat is defined by the mean plane of the four-atom attachment points (r.m.s. deviation = 0.014 Å) of the two bicyclo­heptane substituents. These substituents comprise the pommel and cantle, with each mean plane defined by four atoms proximate to the seat (r.m.s. deviations = 0.001 and 0.000 Å). Relative to the seat, the pommel and cantle bend up 33.36 (5) and 34.22 (4)°, while the benzo units (flaps, r.m.s. deviations = 0.008 and 0.013 Å) bend down 33.48 (4) and 36.58 (4)°.
PMCID: PMC3238874  PMID: 22199727
25.  tert-Butyl (2S)-2-{3-[(R)-bis­(tert-but­oxy­carbon­yl)amino]-2-oxopiperidin-1-yl}-3-methyl­butano­ate1  
The title compound, C24H42N2O7, is a chiral lactam-constrained amino acid with a six-membered ring backbone and isopropyl and tert-butyl ester side chains. The conformation of the six-membered ring can be described as a half chair, with two CH2 C atoms lying 0.443 (1) and −0.310 (1) Å out of the best plane of the other four atoms (mean deviation = 0.042 Å). Both N atoms are sp 2 hybridized, lying 0.0413 (9) and 0.067 (1) Å out of the planes defined by the three C atoms bonded to them. The absolute configuration was determined, based on resonant scattering of light atoms in Cu Kα radiation.
PMCID: PMC3247449  PMID: 22220067

Results 1-25 (28)