Synthesis and Crystal Structure of Sodium Monosulfuron （N-（4-Methylpyrimidin-2-yl）-N＇-2-（nitrophenylsulfonyl） Urea Sodium）

ABSTRACT Monosulfuron is a novel sulfonylurea herbicide with ultra-low dosage invented and patented by Nankai University. Herein its sodium salt was firstly synthesized and crystal structure was determined by X-ray diffraction method. The title compound belongs to the triclinic system, space group P1^- with a = 7.306（6）, b = 9.446（8）, c = 11.872（10）A, α = 76.578（14）, β = 78.049（13）, γ = 77.620（14）°, V = 767.7（11）A^3, Mr = 377.32, Z = 2, Dc = 1.632 g/cm^3,μ= 0.283 mm^-1, F（000） = 388, R = 0.0444 and wR = 0.1186. In the title compound, Na（1） coordinates with 0（4） and 0（5） from one monosulfuron molecule, N（4A） and O（5A） from the other monosulfuron molecule and the oxygen atom from H2O to give five coordination bonds. The title complex is further linked into a three-dimensional structure through π…π interactions and intermolecular hydrogen bonds between the oxygen and nitrogen atoms.     

N-[2-(4-甲基)嘧啶基]-N′-2-硝基苯磺酰脲的合成、晶体结构、生物活性及其与酵母AHAS的分子对接

合成了磺酰脲化合物N-[2-(4-甲基)嘧啶基]-N′-2-硝基苯磺酰脲, 用元素分析、红外、核磁共振氢谱对产物进行了表征, 培养并测定了其晶体结构. 晶体属三斜晶系, 空间群, 晶胞参数a＝0.54159(1) nm, b＝1.1533(3) nm, c＝1.1857(4) nm, α＝83.907(6)°, β＝81.048(5)°, γ＝77.637(4)°, V＝0.7126(4) nm³, D_c＝1.572 g/cm³, Z＝2, F(000)＝348, R＝0.0659, wR＝0.1217. 在晶体结构中, 杂环上的一个N原子与脲桥上邻近的N原子上的H构成分子内氢键. 测定了对酵母AHAS的离体抑制活性, 其抑制常数K_i为(2.48±0.35)×10^－7 mol/L. 用分子对接方法, 将目标化合物晶体结构对接到靶酶酵母AHAS的活性位点, 发现对接完毕目标化合物的构象与复合物晶体中的磺酰脲分子构象接近, 并得到了合理的生物活性预测值. 该研究为进一步理解磺酰脲类的分子结构、药物活性并设计新的分子提供了帮助和指导.     

Synthesis and Crystal Structure of a Sodium Monosulfuron-ester (N-[2'-(4-Methyl)pyrimidinyl]-2-carbomethoxy Benzyl Sulfonylurea Sodium)

Monosulfuron-ester is a novel sulfonylurea herbicide with ultra-low dosage. Herein sodium monosulfuron-ester was synthesized and its crystal structure was determined by X-ray diffraction method. The title compound belongs to monoclinic, space group P21/c with a = 9.335(5), b = 20.632(12), c = 13.853(8) (A), β = 107.193(9)°, Mr = 487.46, Z = 4, Dc = 1.270 g/cm3, μ = 0.293 mm-1, F(000) = 1015, R = 0.0859 and wR = 0.2633. In the title compound, Na coordinates with N(1), O(1) and O(3) from one monosulfuron-ester molecule, N(4A) and O(5A) from the other monosulfuron-ester molecule and one oxygen atom from DMSO to give six coordination bonds.     

新磺酰脲类化合物N-[2-(4-甲基)嘧啶基]-N''''-2-甲氧羰基苯磺酰脲的合成及其二聚体结构

合成并用X-射线晶体衍射法测定了标题化合物 (C14H14N4O5S, Mr = 350.35)的结构。晶体属正交晶系, 空间群为Pna21, 晶胞参数a = 13.242(4), b = 9.478(3), c = 24.889(8) ? V = 3123.7(17) 3, Z = 8, Dc = 1.490 g/cm3, m = 0.241 mm-1, F(000) = 1456。独立可观测点数为3268。最终偏离因子R = 0.0592, wR = 0.1217 (I > 2s(I) 2153), S = 1.122。X-射线衍射证实标题化合物分子晶体中存在2种构型, 分子中苯环所在的位置同嘧啶磺酰脲平面的取向相反。每种构型中嘧啶磺酰脲、苯环及甲氧羰基分别形成3个独立的平面共轭体系。除此之外, 经由O(1)N(6)和N(2)O(6)形成的分子间氢键以及苯环平面间的p-p 相互作用将2个分子结合在一起从而形成二聚结构。     

Synthesis and Crystal Structure of 4-Nitro-2- [（2-diethylaminoethylimino）methyl]phenol

1 INTRODUCTION Schiff base ligands have played an important role in the development of coordination chemistry as they readily form stable complexes with most metal ions[1～4]. These complexes are very interesting in many fields, such as catalysis and enzymatic reac- tions[5, 6], magnetism and molecular architectures[7～9]. The complexes derived from the similar tridentate Schiff base ligand 2-[(2-dimethylaminoethylimino)- methyl]phenol[10, 11] and its derivatives[12～14] have been widely …     

Synthesis, Crystal Structure and Biological Activity of N-(2,6-Difiuorobenzoyl)-N'-[5-(4-trifiuoromethylphenyl)-1,3,4-thiadiazol-2-yl] ure

The title compound N-(2,6-difluorobenzoyl)-N'-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]urea(C17H9F5N4O2S, Mr = 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-l,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 10.7316(13), b = 10.5617(13), c = 16.037(2) (A), β =106.408(2)°, V= 1743.6(4) (A)3, Z = 4, Dc = 1.632 g/cm3, μ = 0.260 mm-1, F(000) = 864, the final R = 0.0599 and wR = 0.1420 for 3467 observed reflections with I ＞ 2o(Ⅰ). The urea group, which adopts a planar configuration mediated by the intramolecular N-H…O hydrogen bond, is nearly coplanar with the thiadiazole and 4-trifluoromethylbenzene rings. The title compound was found to exhibit good fungicidal activity against Rhizoctonia solani and Botrytis cinerea.     

Synthesis,Crystal Structure and Biological Activity of N-（2,6-Difluorobenzoyl）-N＇-[5-（4-trifluoromethyl-phenyl）-1,3,4-thiadiazol-2-yl]ure

The title compound N-(2,6-difluorobenzoyl)-N'-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]urea(C17H9F5N4O2S,Mr = 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-1,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate,and its crystal structure was determined by single-crystal X-ray diffraction.The crystal belongs to monoclinic,space group P21/n with a = 10.7316(13),b = 10.5617(13),c = 16.037(2) ,β = 106.408(2)°,V = 1743.6(4) 3,Z = 4,Dc = 1.632 g/cm3,μ = 0.260 mm-1,F(000) = 864,the final R = 0.0599 and wR = 0.1420 for 3467 observed reflections with I > 2σ(I).The urea group,which adopts a planar configuration mediated by the intramolecular N-H...O hydrogen bond,is nearly coplanar with the thiadiazole and 4-trifluoromethylbenzene rings.The title compound was found to exhibit good fungicidal activity against Rhizoctonia solani and Botrytis cinerea.     

Crystal Structure and Biological Activities of N-(5-(4-Chloro-2-(trifluoromethyl)phenyl)furan-2- carbonyl)-N'-(4,6-dimethylpyrimidin-2-yl)thiourea

The new title compound N-(5-(4-chloro-2-(trifluoromethyl)phenyl)furan-2-carbon-yl)- N?-(4,6-dimethylpyrimidin-2-yl)thiourea (C19H14ClF3N4O2S) has been synthesized, and its crystal structure and biological behaviors were studied. The title compound crystallizes in the monoclinic system, space group P21/c with a = 7.932(5), b = 33.46(2), c = 7.556(5) , β = 98.058(9)°, V = 1986(2) 3, Mr = 454.85, Z = 4, Dc = 1.521 g/cm3, μ = 0.349 mm–1 and F(000) = 928. The structure was solved by direct methods and refined to R = 0.0724 and wR = 0.1429 for 3494 observed reflections (I > 2σ(I)). Intermolecular hydrogen bonds along the b axis together with the continuous π-π interactions construct the three-dimensional architecture of the title compound. The preliminary biological tests show definite herbicidal activity for the title compound.     

Crystal Structure and Biological Activities of N-（5-（4-Chloro-2-（trifluoromethyl）phenyl）furan-2-carbonyl）-N＇-（4,6,dimethylpyrimidin-2-yl）thiourea

The new title compound N-（5-（4-chloro-2-（trifluoromethyl）phenyl）furan-2-carbon-yl）- N＇-（4,6-dimethylpyrimidin-2-yl）thiourea （C19H14C1F3N4O2S） has been synthesized, and its crystal structure and biological behaviors were studied. The title compound crystallizes in the monoclinic system, space group P21/c with a = 7.932（5）, b = 33.46（2）, c = 7.556（5） A, β = 98.058（9）°, V = 1986（2） A^3 Mr = 454.85, Z = 4, Dc = 1.521 g/cm^3, μ = 0.349 mm^-1 and F（000） = 928. The structure was solved by direct methods and refined to R = 0.0724 and wR= 0.1429 for 3494 observed reflections （I 〉 2σ（I））. Intermolecular hydrogen bonds along the b axis together with the continuous π-π interactions construct the three-dimensional architecture of the title compound. The preliminary biological tests show definite herbicidalactivity for the title compound.     

Synthesis and Crystal Structure of N-[4-(4-Methyl-phenylsulfamoyl)-phenyl]-4-methyl-1,2,3-thiadiazole-5-carboxamide

The crystal structure of the title compound (C17H16N4O3S2, Mr = 388.46) has been determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/c with a = 13.688(2), b = 16.704(3), c = 8.3308(12) , β = 99.474(6)o, V = 1878.8(5) 3, Mr = 388.46, Z = 4, Dc = 1.373 g/cm3, μ = 0.308 mm–1, F(000) = 808, R = 0.0389 and wR = 0.0917. X-ray analysis reveals that the crystal structure involves intermolecular N–H…O and N–H…N hydrogen bonds, which link the molecules into a layer parallel to the ac plane.     

Synthesis and Structure Analysis of N-（Dehydroabietyl）maleamic Acid

N-(Dehydroabietyl)maleamic acid was synthesized from dehydroabietylamine and maleic anhydride.Its structure was characterized by IR,1 H-and 13 C-NMR spectra.The stereo structure of the title compound was also unambiguously confirmed by X-ray crystal structure analysis.The white crystal crystallizes in the monoclinic system,space group P2 1 with a=12.075(2),b=10.377(2),c=17.840(4),β=100.31(3) °,V=2199.3(8) 3,R=0.0618 and wR=0.1437.Two crystallographically independent molecules with different conformations co-exist in the unit.In each molecule,the two cyclohexane rings form a trans ring junction with chair and half-chair conformations,respectively.The C=C double bond between two carbonyl groups is in a Z configuration.Intermolecular and intramolecular hydrogen bonds coexist to stabilize the structure.     

Synthesis and Crystal Structure of N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chlorophenyl)benzamide

<正>The title compound N-(2-(1-butyl-3-phenylureido)-1H-indol-3-yl)-N-(4-chloro- phenyl)- benzamide (C_(32)H_(29)ClN_4O_2, M_r = 537.04) was synthesized by a sequential Ugi four com- ponent condensation (4CC)/aza-Wittig/carbodiimide-mediated cyclization, and the structure was characterized by NMR, IR, MS, elemental analysis and X-ray single-crystal diffraction analysis. The crystal belongs to orthorhombic, space group P2_12_12_1 with a = 11.3663(9), b = 13.3248(10), c = 18.7887(15), V = 2845.6(4)~3, Z = 4, D_c = 1.254 mg/m3, μ = 0.170 mm~(-1), F(000) = 1128, the final R = 0.0538 and wR = 0.1187. X-ray analysis reveals that the new five-membered ring (C(14)-C(15)-N(2)-C(16)-C(21)) and the benzene ring (C(16)-C(21)) are nearly coplanar.     

Synthesis and Crystal Structure of Ethyl2—（2—Amino—3—ethoxycarbonyl—4H—benzopyran—4—yl）cyanoacetate

1 INTRODUCTION Inorganic solid supports as catalysts resulting in higher selectivity, milder conditions and easier work-up have been reported as useful catalysts for many reactions [1~3]. Recently, we have reported the Knoevenagel condensation catalyzed by KF-Al2O3[4]. In this paper, we discussed the crystal structure of the title compound synthesized by the reaction of salicylaldehyde and ethyl cyanoacetate in DMF using the catalyst KF-Al2O3 at room temperature KF-Al2O3. In or…     

Synthesis and Crystal Structure of (E)-2-(1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino)-3-(4-hydroxyphenyl)methyl Propionate

(E)-2-(1-(2-Hydroxy-4-methoxyphenyl)ethylideneamino)-3-(4-hydroxyphenyl)methyl propionate (C22H27O6N, Mr = 401.45) has been synthesized by a condensation reaction of paeonol with tyrosin methyl ester hydrochloride, and its structure was determined by IR, NMR, HR MS and X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P21/c, with a = 11.91291(15), b = 9.49947(12), c = 19.8727(3) , β = 106.1104(15)°, V = 2160.60(5)3, Z = 4, Dc = 1.234 g/cm3, μ = 0.739 mm-1, F(000) = 856, R = 0.0466 and wR = 0.1461 for 3859 observed reflections with (Ⅰ> 2σ(Ⅰ)). In the crystal structure, the title compound is constructed by a centrosymmetric dimmer unit composed of a pair of π-π stacking enantiomers, and such units are linked by intermolecular O(5)-H(5)…O(1) and intramolecular N(1)-H(1)…O(1) hydrogen bonds.     

Synthesis,Crystal Structure and Antitumor Activity of N-（4-tert-butyl-5-（4-chlorobenzyl）thiazol-2-yl）-2,6-difluorobenzamide

The title compound was synthesized by the reaction of 4-tert-butyl-5-(4-chlorobenzyl)-2-aminothiazole with 2,6-difluorobenzoic acid. The crystal structure of the title compound, C21H19ClF2N2OS, was determined by single-crystal X-ray diffraction. The crystal belongs to the triclinic system, space group Pbca with a = 12.6479(13), b = 13.1204(13), c = 14.1341(15), Z = 4, V = 2011.5(4)3, Mr = 420.89, Dc = 1.390 g/cm3, S = 1.023, μ = 0.326 mm-1, F(000) = 872, the final R = 0.0365 and wR = 0.0880 for 6101 observed reflections(I 2σ(I)), and R = 0.0507, wR = 0.0978 for 7779 independent reflections. X-ray crystal structure displays that the hydrogen bonding interactions observed link the molecules to form a dimeric unit. The preliminary biological test of the title compound shows good antitumor activity, with IC50 of 0.046 μmol/mL against the Hela cell line.     

Synthesis and Crystal Structure of （5-Hydroxy-6-methoxybenzofuran- 3-yl）-（4-methoxyphenyl）methanone

Compound 1 (5-hydroxy-6-methoxybenzofuran-3-yl)(4-methoxyphenyl)methanone, C17H14O5 , as a potential anti-breast cancer agent has been synthesized under microwave irradiation, which was further converted to (5,6-dihydroxybenzofuran-3-yl)(4-methoxyphenyl)methanone (2). The compounds were characterized by MS and NMR spectra. Meanwhile, the crystal of 1 was obtained and determined by X-ray single-crystal diffraction. Crystal data: monoclinic system, space group P21/n, a=8.908(6), b=10.505(7), c=15.452(11), β=105.043(9)°, V=1396.4(16)3 , Z=4, F(000)=624, Dc=1.419 g/cm3 , μ=0.105 mm1, R=0.0513 and wR=0.1246 for 14459 independent reflections (Rint=0.0647) and 2488 observed ones (I>2σ(I)). Intermolecular O-H···O and π-π stacking interactions contributed to the stability of the structure.     

Synthesis,Crystal Structure and Biological Activity of N-(2-hydroxy-3-(4-(2-methoxyphenyl)-piperazin-1-yl)propyl)quinoxaline-2-methanamide

The title compound N-(2-hydroxy-3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-quinoxaline-2-methanamide(4, C23H27N5O3, Mr = 421.50) was synthesized via a four-step reaction and characterized by 1H NMR, 13 C NMR, ESIMS and single-crystal X-ray diffraction. The crystal is of monoclinic, space group P21/n with a = 12.108(2), b = 12.639(3), c = 14.601(3) , β = 104.87(3)o, V = 2159.6(8) 3, Z = 4, Dc = 1.296 g/cm3, S = 1.023, μ = 0.088 mm-1, F(000) = 896, R = 0.0392 and w R = 0.0983 for 2836 observed reflections with I 2σ(I). The single-crystal X-ray structural analysis reveals that 4 is stabilized by intramolecular and intermolecular hydrogen bonds together with π-π interactions. The bioassay showed that 4 exhibited high selective activity for α1A/D vs. α1B-adrenoceptors subtype.     

Synthesis and Crystal Structure of a Three-dimensional Manganese(Ⅱ)Complex Constructed via Covalent and Hydrogen Bonds

1INTRODUCTIONCrystalengineeringofone-,two-andthree-dimensionalsupramolecularcomplexesiscurrentlyofgreatinterestowingtothefascinatingstructuraldiversityandpotentialapplicationsinmaterials,suchaselectricconductivity,magnetism,host-guestapplication,molecularrecognitionandcatalysis[1,2].Severaltypesofinteractions,suchascoordinationcovalentbond,hydrogenbond,p-pstackingandelectrostaticinteractionscanbeusedtoconstructextendedsupramolecularframeworks[3~6],butcoordinationbondingandhydrogenbondingin…     

Preparation and Crystal Structure of Sodium Hydrogen Epoxysuccinate

1 INTRODUCTION In recent years, sodium hydrogen epoxysuccinatehas gained special attention as a raw material of po-lyepoxysuccinic acid (PESA)[1～3]. We have synthes-ized sodium hydrogen epoxysuccinate by the reac-tion of H2O2 and maleic anhydride in water ca-talyzed by tungstate and obtained its single crystal[1].Its structure was determined by X-ray Nonius CAD4diffractometer. Up to now some crystal structures oforganic carboxyl sodium have been determined[4～6].In this paper we …     

Synthesis,Crystal Structure and Antitumor Activities of N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline

The title compound, N-(2-(1H-indol-3-yl)ethyl)-2-nitroaniline(C16H15N3O2, Mr = 281.31), has been synthesized by the multicomponent reaction of milder Ullmann, and its structure was characterized by 1H NMR, 13 C NMR, IR, H RMS(ESI) and single-crystal X-ray diffraction. It crystallizes in monoclinic, space group I2/c with a = 15.0212(10), b = 9.4911(6), c = 20.3075(13) A, β = 100.776(7)o, V = 2844.1(3)A3, Z = 8, Dc = 1.314 g/cm3, F(000) = 1184.0, μ = 0.089 mm-1, the final R = 0.0574 and w R = 0.1688 for 1701 observed reflections(I 2σ(I)). X-ray analysis indicates three major N(2)–H(2)···O(2), C(13)–H(13)···O(2), N(2)–H(2)···N(3) hydrogen bonds and π-π stacking interactions in the crystal structure. The preliminary biological test shows that the title compound has a good antitumor activity against A549 in vitro with the IC50 value of 35 μmol/L.