The Crystal Structures of (Z)-Ethyl 2-(4-chlorophenyl)-3-(2,4-difluorophenyl-amino)acrylate and its Analogues

Abstract  

The title compound, C₁₇H₁₄ClF₂NO₂, crystallizes in monoclinic space group P2₁/c with unit cell dimension of a = 16.276(3) ?, b = 7.5030(15) ?, c = 13.812(3) ?, α = 90°, β = 111.11(3)°, γ = 90° and Z = 4. The structure of the title compound reveals a Z configuration with respect to the C=C double bond in aminoacrylate fragment. The molecule is stabilized by intramolecular N–H···F and N–H···O hydrogen bonds. In the ethyl 2-aryl-3-arylaminoacrylates, electronic properties of the substituents in the aniline motif clearly affected the attached C–N bond length, and such effect is very little relative to Z-/E-configuration with respect to the C=C double bond.     

Crystal Structure of 3β-Hydroxy-16α-methylpregn-5-en-20-one

Abstract  

The crystal structure of the title compound, 3β-hydroxy-16α-methylpregn-5-en-20-one, C₂₂H₃₄O₂, was determined by direct methods using single crystal X-ray diffraction data. The compound crystallizes in the triclinic space group P1 with unit-cell parameters: a = 6.235(1) ?, b = 6.282(1) ?, c = 12.877(3) ?, α = 96.672(4)°, β = 98.746(4)°, γ = 106.838(4)°, Z = 1. The structure was refined by full-matrix least-squares to R = 0.0573 for 2,196 observed reflections. Rings A and C of the compound are in chair conformation whereas ring B is in half-chair conformation. Ring D is in envelope conformation. The A/B ring junction is quasi-trans, while ring systems B/C and C/D are trans fused about the C8–C9 and C13–C14 bonds, respectively. The steroid nucleus has a small twist, as shown by the C19–C10···C13–C18 pseudo-torsion angle of 8.0°. Molecules are connected via C–H···O hydrogen bonds to form straight chains along the c-axis of the unit cell. The straight chains are packed together to form layers.     

Crystal and Molecular Structure Studies of 1′-Benzyl-8-(4-fluorobenzyl)-8-azaspiro[bicyclo-[3.2.1]octane-3,4′-imidazolodine]-2′,5′-dione

Abstract  

The title compound, C₂₃H₂₃FN₃O₂ has been synthesized and the structure was investigated by X-ray diffraction studies. The compound crystallizes in the triclinic crystal class in the space group P[`1]P\overline{1} with cell parameters a = 9.345(2) ?, b = 10.940(3) ?, c = 11.986(4) ?, α = 72.349(6)°, β = 68.106(18)°, γ = 66.867(5)°, Z = 2 and V = 1027.8(5) ?³. The hydantoin ring adopts a planar conformation and is affected by the π conjugation. The pyrrolidine and piperidine rings in the bicyclo octane moiety adopt envelope and chair conformations respectively. The structure exhibits both inter and intramolecular hydrogen bonds of the type N–H···O, C–H···O and C–H···N. One of the oxygen atoms attached to the hydantoin ring simultaneously accepts two hydrogen bonds to form a three centered hydrogen bonding pattern.     

A Crystallographic Study of S-Methyl 2-(5-Chloro-2-Oxoindolin-3-ylidene)Hydrazinecarbodithioate

Abstract  

S-methyl 2-(5-chloro-2-oxoindolin-3-ylidene)hydrazinecarbodithioate (SM5ClISA) has been prepared from S-methyldithiocarbazate and 5-chloroisatin. The compound crystallized in monoclinic crystal system with space group P 2₁/n, Z = 4, V = 1201.85(7) ?³ and unit cell parameters a = 6.5466(2) ?, b = 7.5056(3) ?, c = 24.6509(8) ?, α = γ = 90° and β = 97.1434(18)°. The crystal structure reveals that the compound exists in the thione form with the chlorine occupies the fifth position in the isatin ring with the bond length of 1.739(2) ?. The 5-chloroisatin moiety is trans with respect to the C3–N2 and C3–S4 bonds whereas the methyl group of the dithiocarbazate moiety is cis with respect to the C3–N2 and C3–S5 bonds.     

Crystal and Molecular Structure of Rhaponticin from Rheum hotaoense

Abstract  

Rhaponticin was isolated from the rhizome and root of Rheum hotaoense C.Y. Cheng et C.T. Kao and its crystal structure was determined by single crystal X-ray diffraction. The compound compactly packs in a triclinic unit cell in the P1 space group with unit cell dimensions a = 5.1240(12) ?, b = 7.0453(17) ?, c = 14.535(4) ?, α = 83.182(3)°, β = 89.212(3)°, γ = 68.956(3)°, V = 1486.0(2) ?³, Z = 1, D _calcd = 1.436 Mg m⁻³ and F(000) = 222. The atoms of the stilbene moiety are nearly coplanar, and the dihedral angle between ring (C2–C7) and ring (C10–C15) is 9.0°. The O–H⋯O hydrogen bonding interactions link the molecules into a complicated 3D framework.     

Synthesis,Crystal Structure and Antibacterial Activity of 5-Bromonicotinic Acid [1-(4-Chlorophenyl)methylidene]hydrazide Monohydrate Methanol Solvate

Abstract  The compound 5-bromonicotinic acid [1-(4-chlorophenyl)methylidene]hydrazide monohydrate methanol solvate, derived from the condensation reaction of 5-bromonicotinic acid hydrazide with 4-chlorobenzaldehyde in a methanol solution, was synthesized and characterized by elemental analysis, IR spectrum, ¹H NMR and X-ray single crystal determination. The compound crystallizes in the triclinic space group P − 1 with unit cell dimensions a = 6.9360(14) ?, b = 10.070(2) ?, c = 12.267(3) ?, α = 84.39(3)°, β = 86.10(3)°, γ = 80.50(3)°, V = 839.8(3) Ǻ³, Z = 2, R ₁ = 0.0724, and wR ₂ = 0.1720. X-ray structure determination reveals that the compound has a trans configuration with respect to the C=N double bond or C–N single bond. In the crystal structure, molecules are linked through intermolecular O–H···N, O–H···O, and C–H···O hydrogen bonds, forming layers parallel to the ab plane. The preliminary biological tests show that the compound has excellent antibacterial activity. Index Abstract  The compound 5-bromonicotinic acid [1-(4-chlorophenyl)methylidene]hydrazide monohydrate methanol solvate, derived from the condensation reaction of 5-bromonicotinic acid hydrazide with 4-chlorobenzaldehyde in a methanol solution, was synthesized and characterized by elemental analysis, IR spectrum, ¹H NMR and X-ray single crystal determination. The molecule of the compound has a trans configuration with respect to the C=N double bond or C–N single bond. In the crystal structure, molecules are linked through intermolecular O–H···N, O–H···O, and C–H···O hydrogen bonds, forming layers parallel to the ab plane. The preliminary biological tests show that the compound has excellent antibacterial activity.      

Crystal Structure Studies of Two Regioisomers of Bromo-4-Aryloxymethylcoumarins

Abstract  

The 4-(2-bromo-4-methyl-phenoxymethyl)-6-methylcoumarin (1) have been synthesized from bromination of corresponding 4-aryloxymethyl coumarin, which is a regioisomer of 4-(2-bromo-4-methyl-phenoxymethyl)-7-methylcoumarin (2) (CCDC-695895). The compound 1 crystallizes with triclinic space group P-1, a = 8.0943(3) ?, b = 9.3502(3) ?, c = 10.1476(4) ?, α = 90.234(2)°, β = 94.065(2)°, γ = 95.106(2)°, Z = 2 and compound 2 crystallizes with monoclinic space group P2₁/n, a = 8.465(5) ?, b = 13.649(5) ?, c = 13.304(5) ?, α = 90.000(5)°, β = 90.740(5)°, γ = 90.000(5)°, Z = 4. Both the compounds are planar with variation in their intermolecular hydrogen bonds between C–H···O and C–H···π.     

Synthesis and Crystal Structure of Heptyl 3-(3,4-dihydroxyphenyl)-2-propenoate

Abstract  The title compound, C₁₆H₂₂O₄, synthesized by modified Knoevenagel condensation of protocatechualdehyde with monoheptyl-malonate and recrystallized from benzene, was confirmed by single-crystal X-ray diffraction (CCDC 272827). The compound crystallizes in triclinic space group Pī with cell parameters a = 5.296(3) ?, b = 10.711(13) ?, c = 13.870(4) ?, α = 98.84(7)°, β = 90.97(4)°, γ = 96.77(7)° and Z = 2. The structure is the E isomer and its packing is stabilized by intermolecular O–H···O and C–H···O hydrogen bonds. Index Abstract  The title compound, C₁₆H₂₂O₄, synthesized by modified Knoevenagel condensation, was confirmed by single-crystal X-ray diffraction showing its structure is in E isomer and its packing is stabilized by hydrogen bonds.      

Structure of a New Bioactive Agent Containing Combined Antibacterial and Antifungal Pharmacophore Sites: 4-{[(<Emphasis Type="Italic">E</Emphasis>)-(5-Bromo-2-hydroxyphenyl)methylidene]amino}-<Emphasis Type="Italic">N</Emphasis>-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide

Abstract  

The title compound (3), C₁₇H₁₄BrN₃O₄S, is a Schiff base compound of 5-bromosalicylaldehyde (1) and sulfamethoxazole (2). The structure of (3) was determined by spectral (IR, ¹H and ¹³C NMR), elemental analyses and X-ray diffraction data. Compound (3) crystallizes in the monoclinic space group C2/c, with a = 31.936(3), b = 6.2571(5), c = 16.903(1) ?, β = 94.867(8), V = 3365.5(5) ?³, Z = 8. In the molecule of compound (3), the molecule is bent at the S atom with a C–SO₂–NH–C torsion angle of −86.3(3)°. Pairs of molecules, related by inversion centres, form intermolecular N–H···N hydrogen bonds to produce a dimer. An intramolecular phenolic O–H···N hydrogen bond is also formed. Intermolecular hydrogen bonding and π–π stacking hold the molecules together. The average distance between stacked benzene ring planes is 3.625(2) ?.     

Synthesis,Crystal Structure and Biological Activity of Two 1,2,3-Thiadiazole Derivatives

Abstract  

The title compounds, quinolin-8-yl 4-methyl-1,2,3-thiadiazole-5-carboxylate 2a and 2-nitrophenyl 4-methyl-1,2,3-thiadiazole-5-carboxylate 2b, synthesized by the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with 8-hydroxyquinoline and 2-nitrophenol, were confirmed by single-crystal X-ray diffraction [CCDC 783328 and 784970]. The 2a crystallizes in triclinic space group P-1 with cell parameters a = 7.957(7) ?, b = 8.378(7) ?, c = 10.097(10) ?, α = 100.63(2)°, β = 112.742(17)°, γ = 93.287(4)° and Z = 2. The 2b crystallizes in triclinic space group P-1 with cell parameters a = 7.134(4) ?, b = 8.154(4) ?, c = 10.254(5) ?, α = 99.501(9)°, β = 91.311(7)°, γ = 109.518(8)° and Z = 2. Packing in the compound 2a is dominated by weak C–H···N and C–H···O hydrogen bonds. In the compound 2b, molecules are linked through intermolecular C–H···O hydrogen bonds interactions. The preliminary bioassay showed that the title compound 2a had excellent antifungal activity with the EC₅₀ detected as from 2.99 to 28.35 μg/mL and the EC₉₀ detected as from 21.041 to 175.17 μg/mL. Both of the title compounds 2a and 2b had good inhibition activity of tobacco mosaic virus (TMV) and good induction activity of tobacco against TMV with potential systemic acquired resistance.     

The Synthesis and Structure of 2-Amino-4,6-dimethylpyrimidine 2-Hydroxybenzoate

Abstract  

The title compound, 2-amino-4,6-dimethylpyrimidine 2-hydroxybenzoate was studied by X-ray diffraction methods. This compound crystallized in a monoclinic system; space group P2(1)/n with the unit cell parameters a = 7.5380(14) ?, b = 20.246(4) ?, c = 9.2029(17) ?, β = 108.594(3), V = 1331.2(4), Z = 4. The hydroxybenzoic acid group has been protonated by the aminopyrimidine moiety. The neighbouring two pyrimidine are bridged by N3–H3A···N2 hydrogen bonds, and the constituting dimers are linked together to form a discrete unit, these units, in turn, are linked together by C–H···O interactions. The protonated N1 atom is attached to the carboxyl group (O2) of the neighbouring phenyl by a hydrogen bond, together with the N3–H3B···O3 hydrogen bond to form a eight-membered ring with graph-set notation R₂¹(8). The C5 and O1 through hydrogen bond forms a supramolecular chain along the b-axis, which is further strengthened by O1–H1···O3 hydrogen bond, bridging the hydroxide radical and carboxyl via hydrogen bonded rings, R₁¹(6).     

1-Phenyldiazenyl-8-Phenylhydrazononaphthalene-7(8H)-One-2-ol: Co-Existence of Azo-Hydroxy and Hydrazo-Keto Forms

Abstract  

The compound crystallizes in the triclinic P[`1] P\bar{1} space group and unit cell dimensions of a = 8.158 ?, b = 12.490 ?, c = 17.129 ?; α = 93.24°, β = 94.72°, γ = 97.61° and Z = 4. The structure was solved by direct methods and refined to an R1 value of 0.0890 on 2,278 observed reflections. There are two molecules in the asymmetric residue unit of the compound. In the title compound C₂₂H₁₆N₄O₂, two diazene groups at C1 and C8 and two hydroxy groups at C2 and C7 bring into play a unique azo-hydrazo equilibrium in which azo-hydroxy and hydrazo-keto forms co-exist in the molecule. The hydrazone H atom and the keto O atom are linked by an intramolecular N–H···O hydrogen bond on the other hand the hydroxy H atom and the azo N atom are linked by two intramolecular O–H···N hydrogen bonds.     

Synthesis,X-Ray Crystal Structure and Spectroscopic Properties of 1,2,3,4-Tetrahydro-2-(thenyl)-3-(<Emphasis Type="Italic">N</Emphasis>-thenylidine)-4-oxoquinazoline

Abstract  

The Schiff base formed between anthraniloyl hydrazide and thiophen-2-aldehyde is synthesized. Reaction of this Schiff base with VOSO₄ in methanol at room temperature does not yield the expected vanadium complex; instead, the Schiff base is transformed to 1,2,3,4-tetrahydro-2-(thenyl)-3-(N-thenylidine)-4-oxoquinazoline, which has been characterized by elemental analyses and by LC–MS, i.r., n.m.r. and electronic spectroscopies. The X-ray crystal structure of the quinazoline product is reported. The compound crystallizes with monoclinic (P2₁/n) space group, and the cell parameters are: a = 5.9442(7) ?, b = 13.6357(15) ?, c = 19.455(2) ?, β = 90.499(2)°. The oxo-quinazoline product is found to be luminescent when excited at its lowest energy transition.     

Crystal Structure,Conformation and Vibrational Analysis of a Mannich Base: 2-[(phenylamino) methyl]-isoindole-1,3-dione

Abstract  

The crystal structure of 2-[(phenylamino) methyl]-isoindole-1,3-dione, C₁₅H₁₂N₂O₂, crystallizes in the triclinic space group Pī with cell parameters of a = 7.1176 (2) ?, b = 8.5533 (3) ?, c = 10.9163 (4) ?, α = 95.937 (2)°, β = 102.975 (2)°, γ = 108.474 (2)°, V = 603.18 (4) ?³ and Z = 2. This indole derivative is a Mannich base in which a methyl group bridges the molecules of phthalimide and aniline molecules. The dihedral angle between the phthalimide and aniline is 75.47 (3)°. The molecules of the title compound forms a centrosymmetric hydrogen-bonded dimer through a pair of N–H···O hydrogen bonds. C–H···π and an extensive π···π interactions, in addition, stabilize the molecular structure. The compound presented here is V-shaped, the angle at the methyl bridge [N–C–N] being 115.04 (12)°. Present study reports the conformation and hydrogen bonding interactions which play an important role in biological functions. Vibration analysis complement the structure analysed.     

Synthesis and Crystal Structures of Two New Schiff Base Hydrazones Derived from Biphenyl-4-Carbohydrazide

Abstract  

The crystal structures of two novel Schiff base hydrazones have been determined by means of the X-ray diffraction. These compounds: N′-[(E)-(2,5-dimethoxyphenyl)methylidene]biphenyl-4-carbohydrazide, C₂₂H₂₀N₂O₃ (1) and N′-[(E)-(4-fluorophenyl)methylidene]biphenyl-4-carbohydrazide, C₂₀H₁₅FN₂O (2), are the first structurally characterized biphenyl derivatives of phenylmethylidene-carbohydrazide. Both compounds crystallize in the monoclinic space groups, 1 in P2₁/c space group with a = 13.987(2) ?, b = 16.426(3) ?, c = 8.214(2) ?, β = 98.12(2)°, and 2 in C2/c with a = 37.163(5) ?, b = 10.696(2) ?, c = 8.098(2) ?, β = 101.18(2)°. Both molecules have very similar bond lengths and angles pattern, even in the differently substituted phenyl ring. However, the conformations of the molecules differ significantly, the more crowded molecule 1 is much more folded than 2. The dihedral angle between the terminal ring planes is 56.17(6)° in 1 while in 2 it is as small as 2.83(14)°. In both structures relatively short and linear N–H···O hydrogen bonds (created by the best available hydrogen bond donor and acceptor) connect molecules into the chains along the unit cell parameter of ca. 8 ? in length. The next stage of the crystal architecture determination, the secondary interactions, are however quite different: in 1 there are almost solely dispersion van der Waals interactions while in 2 some more specific C–H···F and C–H···π interactions are also involved in the crystal packing.     

Synthesis, Crystal and Molecular Structure of 1-(2-Chlorobenzyl)-2-methylthio-1H-benzimidazole

Abstract  

1-(2-Chlorobenzyl)-2-methylthio-1H-benzimidazole compound has been synthesized and characterized by elemental analysis, IR and ¹H-NMR spectroscopy and single crystal X-ray diffraction. The compound crystallizes in the triclinic space group P-1 with unit cell parameters a = 17.201 ?, b = 5.873 ?, c = 24.791 ?, α = 67.410(10)°, β = 74.083(11)°, γ = 81.858(12)°. In the crystal packing, no classic hydrogen bonds are founded, but C–H···π interactions are being between the molecules. The molecular geometry and vibrational frequencies of (C₁₅H₁₃ClN₂S) in the ground state have been calculated by using Hartree–Fock (HF) and Density Functional Method (DFT/B3LYP) with 6-31G(d) basis set. The optimized geometric bond lengths and bond angles obtained by using HF and DFT (B3LYP) show the best agreement with the experimental data.     

Synthesis and Crystal Structures of Dioxomolybdenum(VI) Complexes with ONS-Donor Ligands

Abstract  

Three dioxomolybdenum complexes namely dioxo(5-chlorosalicylaldehyde thiosemicarbazonato) dimethylsulfoxide molybdenum(VI) (C1), dioxo(5-chlorosalicylaldehyde 2-ethylthiosemicarbazonato) dimethylsulfoxide molybdenum(VI) (C2) and dioxo(5-chlorosalicylaldehyde N-phenylthiosemicarbazonato) dimethylsulfoxide molybdenum(VI) (C3) were prepared. The compounds all crystallize in the triclinic space group P-1 with a = 7.3184(3) ?, b = 7.5035(3) ?, c = 14.9713(6) ?, α = 85.005(2)°, β = 85.616(2)°, γ = 66.987(2)° for C1, a = 8.2339(1) ?, b = 10.1739(1) ?, c = 10.4017(1) ?, α = 78.486(1)°, β = 89.312(1)°, γ = 81.730(1)° for C2, a = 7.0591(1) ?, b = 9.5603(1) ?, c = 14.5762(2) ?, α = 76.280(1)°, β = 81.351(1)°, γ = 81.985(1)° for C3. In general, the overall geometry of these complexes can be regarded as a distorted octahedron with the tridentate thiosemicarbazonato ligands (L²⁻) bonded to the MoO₂ ²⁺ core, with the imine nitrogen, phenoxyl oxygen, sulfur atom and one of the terminal oxygen atoms of the dioxomolybdenum occupying the equatorial position. The sixth coordination site is occupied by the dimethylsulfoxide (DMSO) solvent molecules. The adjacent molecules of C1 are linked by N–H···N intermolecular hydrogen bonding, forming polymeric chains that run parallel to the bc plane. On the other hand, C2 is a discrete molecule while the molecules of C3 associate via weak N–H···O hydrogen bonding interaction to form a polymeric chain that runs along the a-axis.     

Characterization of Molecular Complexes of 1,4-Naphthoquinone Derivatives

Abstract  

The structures of sulphur atom tethered quinone containing flexible carboxylic acid (3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-ylsulfanyl)acetic acid (1) and its molecular complex with 4,4′-bipyridine (3) are determined. The compound 1 crystallizes in P-1 (triclinic, a = 7.5378(6) ?, b = 7.6413(7) ?, c = 10.3101(9) ?; α = 89.779 (7)°, β = 81.042 (5)°, γ = 89.101(7)°) and the molecular complex 3 crystallises in P2(1)/n (monoclinic, a = 9.3383(7) ?, b = 3.970(3) ?, c = 42.130(3) ?, β = 91.056(5)°) space groups, respectively. The R₂²(8) type hydrogen bonding between dicarboxylic acid groups present in the parent compound 1 is lost on interaction with 4, 4′-bipyridine; in the molecular complex 3 R₂²(7) type of O···H–C and O–H···N interactions are present between the pyridine rings and carboxylic acid groups. The molecular complex (4) derived from 3-carboxymethylsulfanyl-1,4-dihydroxynaphthalen-2-yl-sulfanyl) acetic acid (2) with triphenylphosphine oxide in 1:2 ratio, crystallises in C2/c space group have monoclinic, a = 26.0494(13) ?, b = 10.5402(5) ?, c = 17.1023(8) ?, β = 108.719 (5)°). The triphenylphosphine oxide molecules are preferentially held by O–H···O interactions between carboxylic acid and P=O bond.     

Hydrogen-Bonded Molecular Ladders and Interlaced Networks in Complexes Built of V-Shaped Molecules 4,4′-Isopropylidenediphenol or 4,4′-Oxydibenzoic Acid with 4,4′-Bipyridine

Abstract  

The title compounds, C₁₀H₈N₂·C₁₅H₁₆O₂ (1) and C₁₀H₈N₂·C₁₄H₁₀O₅ (2), were synthesized by 4,4′-bipyridyl and two similar V-shaped molecules. The two complexes both crystallized in the same space group P2₁/n with the crystal cell parameters: a = 16.0536(3) ?, b = 6.42730(1) ?, c = 21.2717(4) ?, β = 102.330°, V = 2144.21(7) ?³, Z = 4 in compound 1 and a = 7.45020(10) ?, b = 10.0784(2) ?, c = 26.9430(5) ?, β = 92.1140(10)°, V = 2021.67(6) ?³, Z = 4 in compound 2. Compound 1 forms regular molecular chains containing alternative 4,4′-bipyridyl and 4,4′-isopropylidenediphenol units; the molecular components are linked by two types of O–H···N hydrogen bonds. Additionally, every two neighboring chains are connected to be a ladder structure by means of weak C–H···O interactions. In compound 2, 4,4′-bipyridyl and 4,4′-oxydibenzoic acid first construct one-dimensional architecture by strong O–H···N hydrogen bonds, which are similar with the interactions in compound 1. Secondly, two types of weak C–H···O contacts formed between 4,4′-bipyridyl and the acid link one-dimensional chains to be interlaced three-dimensional hydrogen-bonded networks.     

Structures of two N-{2-([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-halophenyl}acetamides

Abstract  

The compounds, N-{2-[(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-chlorophenyl}acetamide (1: X = Cl) and N-{2([(5-amino-1,3,4-thiadiazol-2-yl)difluoromethyl]-4-bromo-phenyl}acetamide (1: X = Br), are isostructural. The molecules are near ‘‘V’’ shaped with the angles between the two aromatic planes ca. 84° in each case. The various intermolecular interactions, namely N–H···O, N–H···N, N–H···F, and C–H···N hydrogen bonds and C–H···π, C–Cl···π and C–O···π interactions, generate 3-D arrays. Compound (1: X = Cl) crystallizes in the monoclinic space group P21/c with a = 16.9032(7) ?, 10.2193(4) ?, c = 7.5227(4) ?, β = 100.179(3)° and Z = 4. Compound (1: X = Br) crystallizes in the monoclinic space group P21/c with a = 17.2119(4) ?, 10.2167(2) ?, c = 7.5677(2) ?, β = 100.326(2)° and Z = 4.