1-[(2-Chloro-3-quinol-yl)meth-yl]indoline-2,3-dione.

In the title compound, C(18)H(11)ClN(2)O(2), the isatin and 2-chloro-3-methyl-quinoline units are both almost planar, with r.m.s. deviations of 0.0075 and 0.0086 Å, respectively, and the dihedral angle between the mean planes of the two units is 83.13 (7)°. In the crystal, a weak inter-molecular C-H⋯ O inter-action links the mol-ecules into chains along the c axis.

(2-Chloro-benzo[h]quinolin-3-yl)methanol.

In the title mol-ecule, C(14)H(10)ClNO, all non-H atoms are coplanar (r.m.s deviation = 0.0266 Å). In the crystal, symmetry-related mol-ecules are hydrogen bonded via inter-molecular O-H⋯O inter-actions, forming chains along the b axis.

5-[1-(3,4-Dichloro-phen-oxy)eth-yl]-1,3,4-oxadiazole-2(3H)-thione hemihydrate.

In the title compound, C(10)H(8)Cl(2)N(2)O(2)S·0.5H(2)O, the atoms in the oxadiazole ring are essentially coplanar (r.m.s. deviation 0.010 Å). The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds involving the water mol-ecule, which is situated on an a twofold rotation axis, and two organic mol-ecules, leading to a thione tautomer in the solid state. The C atom attached to the oxadiazole ring adopts a typical sp(3) hybridization. The dihedral angle between the mean plane of the benzene ring of the dichloro-phenyl group and the mean plane of the oxadiazole ring is 74.18 (4)°. The crystal structure is stabilized by intermolecular N-H⋯O and O-H⋯S hydrogen bonds.

2-Benzoyl-1-(2,4-dichloro-phen-yl)-3-phenyl-guanidine.

In the title compound, C(20)H(15)Cl(2)N(3)O, a typical polysubstituted guanidine with normal geometric parameters, the torsion angles [C-N-C-O = 3.8 (2), N-C-N-C = -6.1 (2)°] indicate that the guanidine and carbonyl groups are almost coplanar, due to the pseudo-hexa-gonal ring formed by intra-molecular N-H⋯O hydrogen bonds. The crystal packing is stabilized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers.

1-(3-Chloro-phen-yl)-3-(2,6-dichloro-benzo-yl)thio-urea.

The structure of the title compound, C(14)H(9)Cl(3)N(2)OS, is composed of discrete mol-ecules with bond lengths and angles quite typical for thio-urea compounds of this class. The plane containing the thio-carbonyl and carbonyl groups subtends dihedral angles of 48.19 (3) and 87.51 (3)° with the planes formed by the 3-chloro and 2,6-dichloro-phenyl rings, respectively; the dihedral angle between the two benzene ring planes is 45.32 (3)°. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation and the mol-ecules form inter-molecular N-H⋯S and N-H⋯O hydrogen bonds, generating a sheet along the a axis.

1-(3-Chloro-benzo-yl)-3-(2,3-dimethyl-phen-yl)thio-urea.

The title mol-ecule, C(16)H(15)ClN(2)OS, exists in the solid state in its thione form with typical thio-urea C-S and C-O bonds lengths, as well as shortened C-N bonds. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation and inter-molecular N-H⋯S hydrogen bonds link the mol-ecules into centrosymmetric dimers. The dihedral angle between the aromatic rings is 50.18 (5)°.

1-(2,6-Dichloro-benzo-yl)-3-(2,3,5,6-tetra-chloro-phen-yl)thio-urea trichloro-methane hemisolvate.

The title compound, C(14)H(6)Cl(6)N(2)OS·0.5CHCl(3), crystallizes with four 1-(2,6-dichloro-benzo-yl)-3-(2,3,5,6-tetra-chloro-phen-yl)thio-urea mol-ecules and two trichloro-methane mol-ecules in the asymmetric unit. The thiourea molecules exist in the solid state in their thione forms with typical thio-urea C-S and C-O bonds lengths, as well as shortened C-N bonds. The -NH-C(=S)-NH-C(=O)- plane is almost perpen-dicular to the benzene ring in each thiourea molecule. Intra-molecular N-H⋯O hydrogen bonds stabilize the mol-ecular conformation and inter-molecular N-H⋯S hydrogen bonds stabilize the packing arrangement.

1-(4-Chloro-phen-yl)-3-(2,4-dichloro-benzo-yl)thio-urea.

The title compound, C(14)H(9)Cl(3)N(2)OS, has bond lengths and angles which are quite typical for thio-urea compounds of this class. The mol-ecule exists in the solid state in its thione form with typical thio-urea C=S and C=O bond lengths, as well as shortened C-N bonds. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular conformation. Inter-molecular N-H⋯S hydrogen bonds link the mol-ecules to form centrosymmetric dimers.

2-Benzoyl-1,1-diethyl-3-phenyl-guanidine.

In the title tetrasubstituted guanidine, C(18)H(21)N(3)O, the guanidine and carbonyl groups are not coplanar, as reflected by the torsion angles involving the N=C atoms [17.6 (3), -141.68 (17) and 42.2 (3)°]. This is probably due to the absence of an intra-molecular N-H⋯O hydrogen bond, forming a six-membered ring, and is commonly observed in this class of compounds. In the crystal structure, centrosymmetric dimers are formed via pairs of inter-molecular N-H⋯O hydrogen bonds. The dihedral angles between the guanidine plane and the phenyl ring and benzoyl plane are38.06 (9) and 41.54 (7)°, respectively.

4-(4-Octyloxybenzo-yloxy)benzoic acid.

The title compound, C(22)H(26)O(5), is an important inter-mediate for the synthesis of side-chain ligands for polymeric liquid crystals. The octyl group is coplanar with the central C(6)O moiety, where the maximum deviation of a C atom in the octyl group from the C(6)O plane is 0.161 (5) Å. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

2-(4-Bromo-phen-oxy)propanohydrazide.

The title compound, C(9)H(11)BrN(2)O(2), is an important inter-mediate for the synthesis of heterocyclic compounds such as azoles, 2,5-disubstituted-1,3,4-oxadiazo-les and 5-substituted 2-mercapto-1,3,4-oxadiazo-les. The bromo-phen-oxy group subtends a dihedral angle of 82.81 (7)° with the plane passing through the propanohydrazide moiety. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds that form columns extending along the b axis.

N-(Benzothia-zol-2-yl)-3-chloro-benzamide.

The title mol-ecule, C(14)H(9)ClN(2)OS, exists in the solid state in its amide form with a typical C=O bond length, as well as shortened C-N bonds. The plane containing the HNCO atoms subtends dihedral angles of 12.3 (4) and 8.1 (3)° with the planes of the phenyl ring and benzothia-zole group, respectively, whereas the dihedral angle between the planes of the phenyl ring and the benzothia-zole group is 5.96 (6)°. In the crystal, mol-ecules form inter-molecular N-H⋯N hydrogen bonds, generating independent scissor-like R(2) (2)(8) dimers.

3-Chloro-N-cyclo-hexyl-benzamide.

In the title mol-ecule, C(13)H(16)ClNO, the mean plane of the atoms in the -CONH- group forms a dihedral angle of 42.0 (4)° with the benzene ring plane. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, generating C(4) chains along [100].

(E)-3-[4-(Pent-yloxy)phen-yl]-1-phenyl-prop-2-en-1-one.

The title compound, C(20)H(22)O(2), crystallizes with two independent mol-ecules in the asymmetric unit. In each mol-ecule, all the non-H atoms lie in a common plane (r.m.s. deviations of 0.098 and 0.079 Å). There is a π-π stacking inter-action in the crystal structure. The central aromatic rings of the two mol-ecules, which are stacked head-to-tail one above the other, are separated by centroid-to-centroid distances of 3.872 (13) and 3.999 (10) Å.

4-Hex-yloxy-3-methoxy-benzaldehyde.

The title compound, C(14)H(20)O(3), is a synthetic analogue with a long aliphatic side chain of the important food additive and flavoring agent, vanillin. There are two independent mol-ecules in the asymmetric unit, each having an essentially planar conformation (r.m.s. deviations of 0.023 and 0.051Å for all non-H atoms of the two mol-ecules in the asymmetric unit).

Adamantane-1-thio-amide.

The title compound, C(11)H(17)NS, is an important inter-mediate for the synthesis of biologically active adamantlythia-zolo-oxadiazo-les. The adamantyl residue is disordered about a twofold rotation axis over two sites with site-occupation factors of 0.817 (3) and 0.183 (3). The crystal structure is stabilized by inter-molecular N-H⋯S hydrogen-bonding inter-actions.

3-(4-Bromo-phenyl-sulfon-yl)-8-methyl-1,3-diaza-spiro-[4.5]decane-2,4-dione.

The crystal structure of the title compound, C(15)H(17)BrN(2)O(4)S, is stabilized by inter-molecular N-H⋯O hydrogen bonds which link the mol-ecules into centrosymmetric dimers. The dihedral angle subtended by the 4-bromo-phenyl group with the mean plane passing through the hydantoin unit is 83.29 (5)°. The cyclo-hexyl group adopts an ideal chair conformation with the methyl group in an equatorial position.

3-(4-Chloro-phenyl-sulfon-yl)-8-methyl-1,3-diaza-spiro-[4.5]decane-2,4-dione.

In the title compound, C(15)H(17)ClN(2)O(4)S, the atoms in the hydantoin ring are coplanar (r.m.s. deviation = 0.006 Å). The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds which link the mol-ecules into centrosymmetric dimers. The dihedral angle subtended by the 4-chloro-phenyl group with the plane passing through the hydantoin unit is 82.98 (4)°. The cyclo-hexyl ring adopts an ideal chair conformation.

Dicyclo-hexyl-ammonium thio-cyanate.

In the crystal structure of the title compound, C(12)H(24)N(+)·NCS(-), the anions and cations are linked through N-H⋯N and N-H⋯S hydrogen bonds, resulting in a chain along the a axis.

[4-(Methoxy-carbon-yl)benz-yl]triphenyl-phospho-nium bromide hemihydrate.

In the crystal structure of the title compound, C(27)H(24)O(2)P(+)·Br(-)·0.5H(2)O, there are inter-molecular O-H⋯Br hydrogen bonds between the H atoms of the water of crystallization and the bromide anions. The three phenyl rings of the triphenyl-phosphonium moiety are at angles of 59.73 (15), 79.15 (14) and 82.81 (17)° with the C/P/C planes.