Crystal structure and Hirshfeld surface analysis of 1-[6-bromo-2-(3-bromo-phen-yl)-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one.

This study presents the synthesis, characterization and Hirshfeld surface analysis of 1-[6-bromo-2-(3-bromo-phen-yl)-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one, C19H18Br2N2O. In the title compound, the pyrrolidine ring adopts a distorted envelope configuration. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O, C-H⋯O and C-H⋯Br hydrogen bonds, forming a three-dimensional network. In addition, pairs of mol-ecules along the c axis are connected by C-H⋯π inter-actions. According to a Hirshfeld surface study, H⋯H (36.9%), Br⋯H/H⋯Br (28.2%) and C⋯H/H⋯C (24.3%) inter-actions are the most significant contributors to the crystal packing.

Synthesis, mol-ecular and crystal structure of [(NH2)2CSSC(NH2)2]2[RuBr6]Br2·3H2O.

The title compound, bis-[di-thio-bis-(formamidinium)] hexa-bromido-ruthenium dibromide trihydrate, [(NH2)2CSSC(NH2)2]2[RuBr6]Br2·3H2O, crystallizes in the ortho-rhom-bic system, space group Cmcm, Z = 4. The [RuBr6]2- anionic complex has an octa-hedral structure. The Ru-Br distances fall in the range 2.4779 (4)-2.4890 (4) Å. The S-S and C-S distances are 2.0282 (12) and 1.783 (2) Å, respectively. The H2O mol-ecules, Br- ions, and NH2 groups of the cation are linked by hydrogen bonds. The conformation of the cation is consolidated by intra-molecular O-H⋯Br, O-H⋯O, N-H⋯Br and N-H⋯O hydrogen bonds. The [(NH2)2CSSC(NH2)2]2+ cations form a hydrogen-bonded system involving the Br - ions and the water mol-ecules. Two Br - anions form four hydrogen bonds, each with the NH2 groups of two cations, thus linking the cations into a ring. The rings are connected by water mol-ecules, forming N-H⋯O-H⋯Br hydrogen bonds.

Crystal structure of bis-[(η5-tert-butyl-cyclo-pentadien-yl)tri-carbonyl-molybdenum(I)](Mo-Mo).

The dinuclear mol-ecule of the title compound, [Mo2(C9H13)2(CO)6] or [Mo( t BuCp)(CO)3]2 where t Bu and Cp are tert-butyl and cyclo-penta-dienyl, is centrosymmetric and is characterized by an Mo-Mo bond length of 3.2323 (3) Å. Imposed by inversion symmetry, the t BuCp and the carbonyl ligands are in a transoid arrangement to each other. In the crystal, inter-molecular C-H⋯O contacts lead to the formation of layers parallel to the bc plane.

Crystal structure and Hirshfeld surface analysis of 1-[6-bromo-2-(4-fluoro-phen-yl)-1,2,3,4-tetra-hydroquinolin-4-yl]pyrrolidin-2-one.

In the title compound, C19H18BrFN2O, the pyrrolidine ring adopts an envelope conformation. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O, C-H⋯O, C-H⋯F and C-H⋯Br hydrogen bonds, forming a three-dimensional network. In addition, C-H⋯π inter-actions connect mol-ecules into ribbons along the b-axis direction, consolidating the mol-ecular packing. The inter-molecular inter-actions in the crystal structure were qu-anti-fied and analysed using Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of dimethyl 2-oxo-4-(pyridin-2-yl)-6-(thio-phen-2-yl)cyclo-hex-3-ene-1,3-di-carboxyl-ate.

In the title compound, C19H17NO5S, the cyclo-hexene ring adopts nearly an envelope conformation. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a three-dimensional network. In addition, C-H⋯π inter-actions connect the mol-ecules by forming layers parallel to the (010) plane. According to the Hirshfeld surface analysis, H⋯H (36.9%), O⋯H/H⋯O (31.0%), C⋯H/H⋯C (18.9%) and S⋯H/H⋯S (7.9%) inter-actions are the most significant contributors to the crystal packing.

Synthesis, crystal structure and Hirshfeld surface analysis of (3Z)-4-[(4-amino-1,2,5-oxa-diazol-3-yl)amino]-3-bromo-1,1,1-tri-fluoro-but-3-en-2-one.

In the title compound, C6H4BrF3N4O2, the oxa-diazole ring is essentially planar with a maximum deviation of 0.003 (2) Å. In the crystal, mol-ecular pairs are connected by N-H⋯N hydrogen bonds, forming dimers with an R 2 2(8) motif. The dimers are linked into layers parallel to the (10) plane by N-H⋯O hydrogen bonds. In addition, C-O⋯π and C-Br⋯π inter-actions connect the mol-ecules, forming a three-dimensional network. The F atoms of the tri-fluoro-methyl group are disordered over two sites in a 0.515 (6): 0.485 (6) ratio. The inter-molecular inter-actions in the crystal structure were investigated and qu-anti-fied using Hirshfeld surface analysis.

Crystal structure and Hirshfeld surface analysis of (Z)-4-oxo-4-{phen-yl[(thio-phen-2-yl)meth-yl]amino}-but-2-enoic acid.

In the title compound, C15H13NO3S, the mol-ecular conformation is stable with the intra-molecular O-H⋯O hydrogen bond forming a S(7) ring motif. In the crystal, mol-ecules are connected by C-H⋯O hydrogen bonds, forming C(8) chains running along the a-axis direction. Cohesion of the packing is provided by weak van der Waals inter-actions between the chains. A Hirshfeld surface analysis was undertaken to investigate and qu-antify the inter-molecular inter-actions. The thio-phene ring is disordered in a 0.9466 (17):0.0534 (17) ratio over two positions rotated by 180°.

Crystal structure and Hirshfeld surface analysis of 3,3'-[ethane-1,2-diylbis(-oxy)]bis-(5,5-di-methyl-cyclo-hex-2-en-1-one) including an unknown solvate.

The title mol-ecule, C18H26O4, consists of two symmetrical halves related by the inversion centre at the mid-point of the central -C-C- bond. The hexene ring adopts an envelope conformation. In the crystal, the mol-ecules are connected into dimers by C-H⋯O hydrogen bonds with R 2 2(8) ring motifs, forming zigzag ribbons along the b-axis direction. According to a Hirshfeld surface analysis, H⋯H (68.2%) and O⋯H/H⋯O (25.9%) inter-actions are the most significant contributors to the crystal packing. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] in PLATON. The solvent contribution was not included in the reported mol-ecular weight and density.

Crystal structure and Hirshfeld surface analysis of (Z)-4-({[2-(benzo[b]thio-phen-3-yl)cyclo-pent-1-en-1-yl]meth-yl}(phen-yl)amino)-4-oxobut-2-enoic acid.

In the title compound, C24H21NO3S, the cyclopentene ring adopts an envelope conformation. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming ribbons along the a axis. Inter-molecular C-H⋯O hydrogen bonds connect these ribbons to each other, forming layers parallel to the (01) plane. The mol-ecular packing is strengthened by van der Waals inter-actions between the layers. The inter-molecular contacts were qu-anti-fied using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing the relative contributions of the contacts to the crystal packing to be H⋯H 46.0%, C⋯H/H⋯C 21.1%, O⋯H/H⋯O 20.6% and S⋯H/H⋯S 9.0%.

Crystal structure and Hirshfeld surface analysis of dimethyl 4'-bromo-3-oxo-5-(thio-phen-2-yl)-3,4,5,6-tetra-hydro-[1,1'-biphen-yl]-2,4-di-carboxyl-ate.

In the title compound, C20H17BrO5S, mol-ecules are connected by inter-molecular C-H⋯S hydrogen bonds with R 2 2(10) ring motifs, forming ribbons along the b-axis direction. C-H⋯π inter-actions consolidate the ribbon structure while van der Waals forces between the ribbons ensure the cohesion of the crystal structure. According to a Hirshfeld surface analysis, H⋯H (40.5%), O⋯H/H⋯O (27.0%), C⋯H/H⋯C (13.9%) and Br⋯H/H⋯Br (11.7%) inter-actions are the most significant contributors to the crystal packing. The thio-phene ring and its adjacent di-carboxyl-ate group and the three adjacent carbon atoms of the central hexene ring to which they are attached were refined as disordered over two sets of sites having occupancies of 0.8378 (15) and 0.1622 (15). The thio-phene group is disordered by a rotation of 180° around one bond.

Crystal structure and Hirshfeld surface analysis of 2,4-di-amino-6-[(1Z,3E)-1-cyano-2,4-di-phenyl-penta-1,3-dien-1-yl]pyridine-3,5-dicarbo-nitrile monohydrate.

The asymmetric unit of the title compound, C25H18N6·H2O, comproses two mol-ecules (I and II), together with a water mol-ecule. The terminal phenyl groups attached to the methyl groups of the mol-ecules I and II do not overlap completely, but are approximately perpendicular. In the crystal, the mol-ecules are connected by N-H⋯N, C-H⋯N, O-H⋯N and N-H⋯O hydrogen bonds with each other directly and through water mol-ecules, forming layers parallel to the (001) plane. C-H⋯π inter-actions between these layers ensure the cohesion of the crystal structure. A Hirshfeld surface analysis indicates that H⋯H (39.1% for mol-ecule I; 40.0% for mol-ecule II), C⋯H/H⋯C (26.6% for mol-ecule I and 25.8% for mol-ecule II) and N⋯H/H⋯N (24.3% for mol-ecules I and II) inter-actions are the most important contributors to the crystal packing.

Crystal structure and Hirshfeld surface analysis of 6-imino-8-(4-methyl-phen-yl)-1,3,4,6-tetra-hydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbo-nitrile.

In the ten-membered 1,3,4,6-tetra-hydro-2H-pyrido[1,2-a]pyrimidine ring system of the title compound, C17H15N5, the 1,2-di-hydro-pyridine ring is essentially planar (r.m.s. deviation = 0.001 Å), while the 1,3-diazinane ring has a distorted twist-boat conformation. In the crystal, mol-ecules are linked by N-H⋯N and C-H⋯N hydrogen bonds, forming a three-dimensional network. In addition, C-H⋯π inter-actions form layers parallel to the (100) plane. Thus, crystal-structure cohesion is ensured. According to a Hirshfeld surface study, H⋯H (40.4%), N⋯H/H⋯N (28.6%) and C⋯H/H⋯C (24.1%) inter-actions are the most important contributors to the crystal packing.

Crystal structure and Hirshfeld surface analysis of 8-benzyl-1-[(4-methyl-phen-yl)sulfon-yl]-2,7,8,9-tetra-hydro-1H-3,6:10,13-diep-oxy-1,8-benzodi-aza-cyclo-penta-decine ethanol hemisolvate.

The asymmetric unit of the title compound, 2C31H28N2O4S·C2H6O, contains a parent mol-ecule and a half mol-ecule of ethanol solvent. The main compound stabilizes its mol-ecular conformation by forming a ring with an R 1 2(7) motif with the ethanol solvent mol-ecule. In the crystal, mol-ecules are connected by C-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network. In addition, C-H⋯π inter-actions also strengthen the mol-ecular packing.

Crystal structure and Hirshfeld surface analysis of 4-oxo-3-phenyl-2-sulfanyl-idene-5-(thio-phen-2-yl)-3,4,7,8,9,10-hexa-hydro-2H-pyrido[1,6-a:2,3-d']di-pyrimidine-6-carbo-nitrile.

In the title compound, C21H15N5OS2, mol-ecular pairs are linked by N-H⋯N hydrogen bonds along the c-axis direction and C-H⋯S and C-H⋯O hydrogen bonds along the b-axis direction, with R 2 2(12) and R 2 2(16) motifs, respectively, thus forming layers parallel to the (10) plane. In addition, C=S⋯π and C≡N⋯π inter-actions between the layers ensure crystal cohesion. The Hirshfeld surface analysis indicates that the major contributions to the crystal packing are H⋯H (43.0%), C⋯H/H⋯C (16.9%), N⋯H/H⋯N (11.3%) and S⋯H/H⋯S (10.9%) inter-actions.

Syntheses, characterizations, crystal structures and Hirshfeld surface analyses of methyl 4-[4-(di-fluorometh-oxy)phen-yl]-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate, isopropyl 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate and tert-butyl 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

The crystal structures and Hirshfeld surface analyses of three similar compounds are reported. Methyl 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate, (C21H23F2NO4), (I), crystallizes in the monoclinic space group C2/c with Z = 8, while isopropyl 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carb-oxyl-ate, (C23H27F2NO4), (II) and tert-butyl 4-[4-(di-fluoro-meth-oxy)phen-yl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate, (C24H29F2NO4), (III) crystallize in the ortho-rhom-bic space group Pbca with Z = 8. In the crystal structure of (I), mol-ecules are linked by N-H⋯O and C-H⋯O inter-actions, forming a tri-periodic network, while mol-ecules of (II) and (III) are linked by N-H⋯O, C-H⋯F and C-H⋯π inter-actions, forming layers parallel to (002). The cohesion of the mol-ecular packing is ensured by van der Waals forces between these layers. In (I), the atoms of the 4-di-fluoro-meth-oxy-phenyl group are disordered over two sets of sites in a 0.647 (3): 0.353 (3) ratio. In (III), the atoms of the dimethyl group attached to the cyclo-hexane ring, and the two carbon atoms of the cyclo-hexane ring are disordered over two sets of sites in a 0.646 (3):0.354 (3) ratio.

Crystal structure and Hirshfeld surface analysis of (E)-2-[2-(2-amino-1-cyano-2-oxo-ethyl-idene)hydrazin-1-yl]benzoic acid N,N-di-methylformamide monosolvate.

In the title compound, C10H8N4O3·C3H7NO, the asymmetric unit contains two crystallographically independent mol-ecules A and B, each of which has one DMF solvate mol-ecule. Mol-ecules A and B both feature intra-molecular N-H⋯O hydrogen bonds, forming S(6) ring motifs and consolidating the mol-ecular configuration. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds connect mol-ecules A and B, forming R 2 2(8) ring motifs. Weak C-H⋯O inter-actions link the mol-ecules, forming layers parallel to the (12) plane. The DMF solvent mol-ecules are also connected to the main mol-ecules (A and B) by N-H⋯O hydrogen bonds. π-π stacking inter-actions [centroid-to-centroid distance = 3.8702 (17) Å] between the layers also increase the stability of the mol-ecular structure in the third dimension. According to the Hirshfeld surface study, O⋯H/H⋯O inter-actions are the most significant contributors to the crystal packing (27.5% for mol-ecule A and 25.1% for mol-ecule B).

Crystal structure and Hirshfeld surface analysis of 4-(2-chloro-eth-yl)-5-methyl-1,2-di-hydro-pyrazol-3-one.

In the crystal of the title compound, C6H9ClN2O, mol-ecular pairs form dimers with an R 2 2(8) motif through N-H⋯O hydrogen bonds. These dimers are connect into ribbons parallel to the (100) plane with R 4 4(10) motifs by N-H⋯O hydrogen bonds along the c-axis direction. In addition, π-π [centroid-to-centroid distance = 3.4635 (9) Å] and C-Cl⋯π inter-actions between the ribbons form layers parallel to the (100) plane. The three-dimensional consolidation of the crystal structure is also ensured by Cl⋯H and Cl⋯Cl inter-actions between these layers. According to a Hirshfeld surface study, H⋯H (43.3%), Cl⋯H/H⋯Cl (22.1%) and O⋯H/H⋯O (18.7%) inter-actions are the most significant contributors to the crystal packing.

Crystal structure and Hirshfeld surface analysis of (2E)-1-phenyl-3-(1H-pyrrol-2-yl)propen-1-one.

The title com-pound, C13H11NO, adopts an E configuration about the C=C double bond. The pyrrole ring is inclined to the phenyl ring at an angle of 44.94 (8)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, forming ribbons parallel to (020) in zigzag C(7) chains along the a axis. These ribbons are connected via C-H⋯π inter-actions, forming a three-dimensional network. No significant π-π inter-actions are observed.

Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-di-chloro-1-[(E)-phenyl-diazen-yl]eth-enyl}benzoate, methyl 4-{2,2-di-chloro-1-[(E)-(4-methyl-phen-yl)diazen-yl]ethen-yl}benzoate and methyl 4-{2,2-di-chloro-1-[(E)-(3,4-di-methyl-phen-yl)diazen-yl]ethen-yl}benzoate.

The crystal structures and Hirshfeld surface analyses of three similar azo compounds are reported. Methyl 4-{2,2-di-chloro-1-[(E)-phenyl-diazen-yl]ethen-yl}benzoate, C16H12Cl2N2O2, (I), and methyl 4-{2,2-di-chloro-1-[(E)-(4-methyl-phen-yl)diazen-yl]ethen-yl}benzoate, C17H14Cl2N2O2, (II), crystallize in the space group P21/c with Z = 4, and methyl 4-{2,2-di-chloro-1-[(E)-(3,4-di-methyl-phen-yl)diazen-yl]ethen-yl}benzoate, C18H16Cl2N2O2, (III), in the space group P with Z = 2. In the crystal of (I), mol-ecules are linked by C-H⋯N hydrogen bonds, forming chains with C(6) motifs parallel to the b axis. Short inter-molecular Cl⋯O contacts of 2.8421 (16) Šand weak van der Waals inter-actions between these chains stabilize the crystal structure. In (II), mol-ecules are linked by C-H⋯O hydrogen bonds and C-Cl⋯π inter-actions, forming layers parallel to (010). Weak van der Waals inter-actions between these layers consolidate the mol-ecular packing. In (III), mol-ecules are linked by C-H⋯π and C-Cl⋯π inter-actions forming chains parallel to [011]. Furthermore, these chains are connected by C-Cl⋯π inter-actions parallel to the a axis, forming (01) layers. The stability of the mol-ecular packing is ensured by van der Waals forces between these layers.

Crystal structure and Hirshfeld surface analysis of dieth-yl (3aS,3a1R,4S,5S,6R,6aS,7R,9aS)-3a1,5,6,6a-tetra-hydro-1H,3H,4H,7H-3a,6:7,9a-di-epoxy-benzo[de]isochromene-4,5-di-carboxyl-ate.

In the title compound, C18H22O7, two hexane rings and an oxane ring are fused together. The two hexane rings tend toward a distorted boat conformation, while the tetra-hydro-furan and di-hydro-furan rings adopt envelope conformations. The oxane ring is puckered. The crystal structure features C-H⋯O hydrogen bonds, which link the mol-ecules into a three-dimensional network. According to a Hirshfeld surface study, H⋯H (60.3%) and O⋯H/H⋯O (35.3%) inter-actions are the most significant contributors to the crystal packing.