N-(4-Bromo-phen-yl)acetamide: a new polymorph.

A new polymorph of the title compound, C8H8BrNO, has been determined at 173 K in the space group P21/c. The previous room-temperature structure was reported to crystallize in the ortho-rhom-bic space group Pna21 [Andreetti et al. (1968 ▶). Acta Cryst. B24, 1195-1198]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds forming chains along [010]. Weak C-H⋯π inter-actions are also present.

(2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-[4-(methyl-sulfan-yl)phen-yl]prop-2-en-1-one.

In the title compound, C(29)H(22)F(2)O(2)S, the central benzene ring makes dihedral angles of 45.83 (7), 38.90 (7) and 55.50 (7)° with the two fluoro-substituted benzene rings and the methyl-sulfanyl-substituted benzene ring, respectively. In the crystal, C-H⋯O contacts connect the mol-ecules into layers lying perpendicular to the c axis. In addition, π-π stacking inter-actions between one of the fluoro-phenyl groups [centroid-centroid distances = 3.681 (1) and 3.818 (1) Å] are observed.

2-[3,5-Bis(4-meth-oxy-phen-yl)-4,5-di-hydro-1H-pyrazol-1-yl]-4,6-bis-(4-meth-oxy-phen-yl)pyrimidine.

In the title compound, C(35)H(32)N(4)O(4), the pyrazole ring forms a dihedral angle of 15.04 (8)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.95 (8) and 1.86 (7)° with its adjacent meth-oxy-substituted benzene rings, whereas the equivalent angles are 80.24 (9) and 11.55 (9)° for the pyrazole ring and its adjacent benzene rings. The crystal packing features π-π inter-actions, the centroid-centroid distance between the pyrimidine and methoxyphenyl rings being 3.604 (1) Å. The pyrazole ring is nearly planar, with a maximum deviation of 0.020 (3) Šfor the -CH(2)- carbon.

(2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(2-fluoro-phen-yl)prop-2-en-1-one.

In the title compound, C(28)H(19)F(3)O(2), the central benzene ring forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)° with the fluoro-benzene rings. In the crystal, inter-molecular C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules, forming an undulating two-dimensional network parallel to the bc plane. C-H⋯π inter-actions further consolidate the crystal packing.

N-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)-4,4''-difluoro-5'-hy-droxy-1,1':3',1''-terphenyl-4'-carboxamide.

The asymmetric unit of the title compound, C(27)H(16)F(2)N(2)O(4), consists of two crystallographically independent mol-ecules (A and B). In mol-ecule 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 mol-ecule 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 mol-ecule B. The isoindoline ring system in mol-ecule A and the major and minor components of the disordered isoindoline ring system in mol-ecule 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 intra-molecular O-H⋯O hydrogen bond generates an S(6) ring in each mol-ecule. In the crystal, mol-ecules 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).

1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)ethanone.

In the title compound, C(21)H(16)F(2)O(2), the central benzene ring is inclined at dihedral angles of 30.91 (8) and 46.88 (7)° to the two terminal fluoro-substituted rings. The dihedral angle between the two terminal fluoro-subsituted rings is 68.34 (8)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by weak C-H⋯π inter-actions.

Ethyl 4,4''-difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-carboxyl-ate.

In the title compound, C(22)H(18)F(2)O(3), the two fluoro-substituted rings form dihedral angles of 25.89 (15) and 55.00 (12)° with the central benzene ring. The eth-oxy group in the mol-ecule is disordered over two positions with a site-occupancy ratio of 0.662 (7):0.338 (7). In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into chains along the a axis. The crystal packing is further stabilized by C-H⋯π and π-π inter-actions, with centroid-centroid distances of 3.8605 (15) Å.

(1E,4E)-1-(3-Nitro-phen-yl)-5-phenyl-penta-1,4-dien-3-one.

In the title compound, C(17)H(13)NO(3), the dihedral angle between the benzene rings is 31.21 (5)°. In the crystal, inversion dimers linked by pairs of C-H⋯O hydrogen bonds occur. A C-H⋯π inter-action is also indicated.

(2E)-2-[(3E)-4-Phenyl-but-3-en-2-yl-idene]hydrazinecarboxamide.

In the title compound, C(11)H(13)N(3)O, the phenyl ring is disordered over two sites, with occupancy factors in a 0.520 (17):0.480 (17) ratio. The dihedral angle between the ring planes of the major and minor components of the disordered ring is 12.9 (2)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming R(2) (2)(8) ring motifs. C-H⋯O, C-H⋯N and C-H⋯π inter-actions also occur.

[2,6-Bis(biphenyl-4-yl)-4-hy-droxy-4-(pyridin-2-yl)cyclo-hexane-1,3-di-yl]bis-[(pyridin-2-yl)methanone]-butan-2-one (1/1).

In the title solvate, C(47)H(37)N(3)O(3)·C(4)H(8)O, the cyclo-hexane ring adopts a chair conformation and the plane through its near coplanar atoms forms dihedral angles of 82.58 (7), 89.27 (7), 60.30 (8), 54.54 (7) and 72.03 (7)°, respectively, with the three pyridine rings and the two attached benzene rings. The rings of the biphenyl units are twisted from each other, making dihedral angles of 35.27 (7) and 45.41 (7)°. All the rings are in equatorial orientations in the cyclo-hexane ring, except for the C=O-bonded pyridine ring in position 1, which is axial. Intra-molecular O-H⋯N and C-H⋯O hydrogen bonds form one S(5) and three S(6) ring motifs. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds into a chain along the c axis. The crystal structure also features weak C-H⋯π inter-actions and aromatic π-π stacking [centroid-centroid distances = 3.5856 (10) and 3.7090 (9) Å].

3,5-Bis(4-fluoro-phen-yl)isoxazole.

In the crystal structure of the title compound, C(15)H(9)F(2)NO, the complete mol-ecule is generated by a crystallographic twofold rotation axis and the O and N atoms of the central isoxazole ring are statistically disordered with equal site occupancies. The terminal benzene rings form a dihedral angle of 24.23 (3)° with the isoxazole ring. The dihedral angle between the benzene rings is 47.39 (2)°. No significant inter-molecular inter-actions are observed.

(2E)-3-(4-Cyano-phen-yl)-1-(4,4''-difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one.

In the title compound, C(29)H(19)F(2)NO(2), the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyano-benzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluoro-benzene rings. In the crystal, C-H⋯O and C-H⋯F hydrogen bonds link the mol-ecules into sheets lying parallel to the ab plane. The crystal packing also features C-H⋯π inter-actions involving the central benzene ring.

1-[3-(4-Chloro-phen-yl)-5-(4-meth-oxy-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(18)H(17)ClN(2)O(2), the benzene rings form dihedral angles of 6.69 (6) and 74.88 (5)° with the 4,5-dihydro-1H-pyrazole ring. The benzene rings form a dihedral angle of 76.67 (5)° with each other. In the crystal, mol-ecules are linked via bifurcated (C,C)-H⋯O hydrogen bonds into chains along [010]. The crystal structure is further consolidated by C-H⋯π inter-actions.

1-[3-(4-Chloro-phen-yl)-5-(4-meth-oxy-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]butan-1-one.

In the title compound, C(20)H(21)ClN(2)O(2), the benzene rings form dihedral angles of 6.35 (5) and 81.82 (5)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.145 Å). This latter ring adopts an envelope conformation with the CH grouping as the flap. The dihedral angle between the benzene rings is 75.63 (4)°. In the crystal, mol-ecules are linked by C-H⋯Cl and C-H⋯O hydrogen bonds into chains along [-201]. The crystal structure also features C-H⋯π inter-actions.

(2E)-3-(2-Bromo-phen-yl)-1-(4,4''-difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one.

In the title compound, C(28)H(19)BrF(2)O(2), the central benzene ring makes dihedral angles of 62.51 (18), 46.23 (18) and 48.19 (18)° with the bromo-substituted benzene ring and two terminal fluoro-substituted benzene rings, respectively. In the crystal, mol-ecules are linked by C-H⋯F hydrogen bonds into infinite chains along [110]. Weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.683 (2) Å] also occur and short inter-molecular F⋯F contacts [2.833 (4) Å] are observed.

(E)-3-(2-Chloro-phen-yl)-1-(4,4''-difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one.

The title compound, C(28)H(19)ClF(2)O(2), is a polysubstituted terphenyl derivative bearing a Michael system in which the C=C double bond has an E conformation. In the crystal, C-H⋯Cl and C-H⋯O contacts connect the mol-ecules into layers lying perpendicular to the a axis. The shortest inter-centroid distance between symmetry-related 4-fluoro-phenyl groups is 3.7547 (16) Å.

(2E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(2,6-difluoro-phen-yl)prop-2-en-1-one.

In the title compound, C(28)H(18)F(4)O(2), the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluoro-benzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluoro-benzene rings is 87.81 (6)°. The meth-oxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C-O-C(ar)-C(ar) [-0.06 (15)°] and C-C-C(ar)-C(ar) [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, mol-ecules are linked by C-H⋯F and C-H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C-H⋯π inter-actions.

N'-[(E)-4-Hy-droxy-benzyl-idene]-2-(naph-tha-len-2-yl-oxy)acetohydrazide.

The asymmetric unit of the title compound, C(19)H(16)N(2)O(3), contains two independent mol-ecules in which the dihedral angles between the naphthalene ring system and the benzene ring are 10.0 (1) and 35.3 (1)°. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming a two-dimensional framework parallel to (001). Weak C-H⋯O and C-H⋯N hydrogen bonds complete a three-dimensional network.

Ethyl 2-amino-4,6-bis-(4-fluoro-phen-yl)cyclo-hexa-1,3-diene-1-carboxyl-ate.

In the title compound, C(21)H(19)F(2)NO(2), the cyclo-hexa-1,3-diene ring is in a distorted envelope conformation. The dihedral angles between the mean planes of the diene moiety and the two fluoro-phenyl rings are 42.8 (2) and 75.0 (5)°. The two fluoro-phenyl rings are inclined to one another by 87.0 (3)°. In the crystal, intra-molecular N-H⋯O hydrogen bonds and weak N-H⋯O and N-H⋯F inter-molecular inter-actions are observed forming an infinite two-dimensional network along [011].

(6Z)-3,5-Bis(4-fluoro-phen-yl)-6-(1-hy-droxy-ethyl-idene)cyclo-hex-2-en-1-one.

In the title compound, C(20)H(16)F(2)O(2), the cyclo-hex-2-en-1-one ring adopts a distorted envelope conformation and the dihedral angles between its six-atom mean plane and the fluorophenyl rings are 38.9(8) and 82.3(1)°. The two fluoro-phenyl rings are oriented at an angle of 77.3 (3)°. The long hy-droxy O-H bond length of 1.22 (3) and the H⋯O distance of 1.28 (3) Å, together with a longer than expected C=O bond length [1.290 (2) Å] in the hy-droxy(en-1-one) group, indicate sharing of the H atom as O⋯H⋯O between the two O atoms and the influence of electron delocalization. Weak C-H⋯O inter-molecular inter-actions form an infinite two-dimensional network in (011).