Crystal structure of 1,3-dimethylbenzimidazole-2-selenone, C9H10N2Se
Crystal structure of 1,3-dimethylbenzimidazole-2-selenone, C9H10N2Se
复制标题
1,3-二甲基苯并咪唑-2-硒酮的晶体结构，C9H10N2Se
DOI：
10.1515/ncrs-1999-0273
复制
发表时间：
1999
期刊：
影响因子：
--
通讯作者：
F. Ercan
中科院分区：
文献类型：
--
作者：
A. Aydın;H. Soylu;H. Kügükbay;Μ. Akkurt;F. Ercan
C9HioN2Se，单斜，P\2\！n \(14号)= 7.414 (1)a, b = 14.339 (1) a, c = 9.225(1),β= 107.70(1)°,V = 934.2,Ζ= 4,RgiF) = 0.038, Rv4F) = 0。115, t = 293 k。将硒（0.56 g; 7.16 mmol）加入到二甲基3 -二甲基苯并咪唑-2-酰基)（0.95 g; 3.25 mmol）的甲苯溶液中（25 cm），回流加热4 h，热过滤去除多余的硒。冷却后的溶液，以适应。323 Κ戊烷（15cm）加入。将溶液冷却至243 Κ，得到标题化合物的白色晶体（1.4 g; 96%, mp = 433 Κ 434 Κ）。所有反应均在氩气或氮气气氛下进行，采用施伦克技术[1]。用标准方法对溶剂进行脱氧和干燥，讨论富电子烯烃是强还原剂。已知富电子烯烃[3-5]与空气氧化的最终产物是尿素；硫、硒和碲类似地反应形成相应的类似物[6,7]。氧化速率强烈依赖于电子的可用性，因此依赖于氮上的取代基。人们对含有咪唑烷部分的环脲进行了广泛的研究，包括它们的x射线晶体结构[8]。对含有苯并咪唑基团的环脲的研究较少，也没有已知的x射线晶体结构测定的例子。本研究的目的是阐明先前合成的含有苯并咪唑基团[9]的环脲的晶体结构，并与咪唑类似物进行比较。在该化合物中，Nl-Cl和N2-C1键长与二（1 -甲基-乙基苯并咪唑烷-2- yum）四氟硼酸[10]中的Nl-Cl和N2-C1键长几乎相似。Nl -Cl键长为1.377(8)Ä， N2-C1键长为1.382(8)Ä。表1。数据收集和处理。晶体：乳状，棱镜形，尺寸0.35 χ 0.40 χ 0.40 mm波长：Mo Ka辐射(0.71073 A) μ: 39.64 cm“1衍射仪，扫描模式：Enraf-Nonius CAD4， oV20 20max: 45.38°NfMijmeasured， N(hkl)unique: 1157,1157标准为/0bs， N(hkl)gc /obs > 2 o(/0bs), 1026 N（param）定义：110程序：SHELXS-86 [11]， SHELXL-97 [12]， ORTEPII[13]表2。原子坐标和位移参数（在A中）。原子站点X yζUi所以H (3) 4 e 0.1576 0.152 1.2302 0.092 H (4) 4 e 0.2295 0.0226 1.369 0.114 H (5) 4 e 0.3157 -0.1175 1.2765 0.117 H (6) 4 e 0.3176 -0.1237 1.0178 - 0.095 H (8 a) 4 e 0.0854 0.2875 0.8401 0.133 H (8 b) 4 e 0.1888 0.2899 1.0157 0.133 H (8 c) 4 e -0.022 0.2561 0.9543 0.133 H (9) 4 e 0.2934 -0.0941 0.773 0.117 H (9 b) 4 e 0.3509 -0.0162 0.6763 0.117 H (9 c) 4 e 0.1376 -0.0443 0.6419 0.117 *通讯作者(电子邮件:bgunes@sirius.gazi.edu.tr) 296 l, 3-Dimethylbenzimidazole-2-selenone表3。原子坐标和位移参数（在A中）。原子站点X yζUu U22 t / 33 U 2 Uu t / 23 Se (l) 4 e 0.1494 (1) 0.18246 (5) 0.61588 (8) 0.109 0.068 0.089 (1) (1) (1) -0.0027 (3) 0.0302 (6) 0.0128 (3) N (l) 4 e 0.1634 (8) 0.1610 (4) 0.9286 (7) 0.078 (3) 0.068 (3) 0.068 (4) -0.005 (3) 0.030 (3) -0.009 (3) N (2) 4 e 0.2334 (7) 0.0346 (3) 0.8287 (5) 0.069 (3) 0.071 (3) 0.048 (3) -0.001 (2) 0.013 (2) -0.002 (2) C (l) 4 e 0.1830 (8) 0.1230 (5) 0.7971 (7) 0.061 (3) 0.063 (4) 0.076 (4) -0.014 (3) 0.022 (3) -0.008 (3) C (2) 4 e 0.1993 (8) 0.0968 (4) 1.0414 0.073 0.058 (7) (3) (4) 0.054 (4) -0.007 (3)0.015 (3) -0.007 (3) C (3) 4 e 0.192 (1) 0.0981 (6) 1.1888 (8) 0.083 (4) 0.094 (5) 0.054 (4) -0.013 (4) 0.023 (3) -0.006 (4) C (4) 4 e 0.233 (1) 0.0210 (8) 1.269 (1) 0.079 (5) 0.146 (8) 0.059 (5) -0.019 (5) 0.018 (3) -0.002 (5) C (5) 4 e 0.285 (1) -0.0654 (6) 1.214 (1) 0.083 (5) 0.124 (7) 0.081 (5) -0.015 (4) 0.016 0.037 (4) (5) (6) 4 e 0.288加元(1)-0.0694 (5)1.0606 (9)0.080 (4)0.070 (4)0.080 (5)-0.008 0.013 0.015 (3)(4)(4)(7)4 e 0.2431加元(8)0.0131 (5)0.9794 (7)0.061 0.062 0.087 (3)(4)(4)-0.012 (3)0.023 (3)-0.002 (3)C (8) 4 e 0.098 (1)0.2569 (6) 0.9352 (9) 0.092 (5) 0.078 (5) 0.099 (5) -0.001 (4) 0.034 (4) -0.014 (4) C (9) 4 e 0.256(1) -0.0361(5) 0.7206(9) 0.091(5) 0.076(4) 0.075(5) 0.009(3) 0.036(4) -0.003(4)致谢。在此，我们对购买CAD4衍射仪表示感谢。土耳其科学技术研究理事会大DPT/TBAG1。
C9HioN2Se, monoclinic, P\2\!n\ (No. 14), a = 7.414(1) Ä, b = 14.339(1) Ä, c = 9.225(1) Ä, β = 107.70(1)°, V= 934.2 Ä, Ζ = 4, RgiF) = 0.038, Rv4F) = 0 .115 ,T= 293 K. Source of material Selenium (0.56 g; 7.16 mmol) was added to a solution of bis(l,3dimethylbenzimidazolidine-2-ylidene) (0.95 g; 3.25 mmol) in toluene (25 cm) and heated under reflux for 4 h. Then the solution was filtered while hot to remove excess of selenium. After cooling the solution to apprpx. 323 Κ pentane (15 cm) was added. Upon cooling the solution to 243 Κ white crystalls of the title compound were obtained (1.4 g; 96%, mp = 433 Κ 434 Κ). All reactions were performed under an argon or nitrogen atmosphere with use of schlenk techniques [1]. The solvents were deoxygenated and dried by standard methods [2], Discussion Electron-rich olefins are powerful reducing agents [3]. It is known that the ultimade oxidation product of electron-rich olefins [3-5] with air is urea; sulphur, selenium and tellurium react similarly to form the corresponding anologues [6,7], The oxidation rate is strongly dependent on the availability of electrons and hence on the substituents on the nitrogen. There are extensive studies about cyclic ureas having imidazolidine moiety including their X-ray crystal structure [8]. Less attention has been paid to the cyclic urea which contains benzimidazole moiety and there is no example known for the X-ray crystal structure determination. The aim of this study was to elucidate crystal structure of previously synthesised cyclic urea having benzimidazole moiety [9] and compare with imidazole analogues. In the compound, Nl-Cl and N2-C1 bond lengths resemble almost with Nl -Cl and N2-C1 bond lengths in the bis( 1 -methyl3-ethylbenzimidazolidine-2-ylium) tetrafluoroborate [10]. The Nl -Cl bond length is 1.377(8) Ä and N2-C1 bond length is 1.382(8) Ä. Table 1. Data collection and handling. Crystal: cream, prismatic, size 0.35 χ 0.40 χ 0.40 mm Wavelength: Mo Ka radiation (0.71073 A) μ: 39.64 cm" 1 Diffractometer, scan mode: Enraf-Nonius CAD4, oV20 20max: 45.38° NfMijmeasured, N(hkl)unique: 1157,1157 Criterion for /0bs, N(hkl)gc /obs > 2 o(/0bs), 1026 N(param)Te fined: 110 Programs: SHELXS-86 [11], SHELXL-97 [12], ORTEPII [13] Table 2. Atomic coordinates and displacement parameters (in A). Atom Site X y ζ Ui so H(3) 4e 0.1576 0.152 1.2302 0.092 H(4) 4e 0.2295 0.0226 1.369 0.114 H(5) 4e 0.3157 -0.1175 1.2765 0.117 H(6) 4e 0.3176 -0.1237 1.0178 0.095 H(8A) 4e 0.0854 0.2875 0.8401 0.133 H(8B) 4e 0.1888 0.2899 1.0157 0.133 H(8C) 4e -0.022 0.2561 0.9543 0.133 H(9A) 4e 0.2934 -0.0941 0.773 0.117 H(9B) 4e 0.3509 -0.0162 0.6763 0.117 H(9C) 4e 0.1376 -0.0443 0.6419 0.117 * Correspondence author (e-mail: bgunes@sirius.gazi.edu.tr) 296 l,3-Dimethylbenzimidazole-2-selenone Table 3. Atomic coordinates and displacement parameters (in A). Atom Site X y ζ Uu U22 t/33 U,2 Uu t/23 Se(l) 4e 0.1494(1) 0.18246(5) 0.61588(8) 0.109(1) 0.089(1) 0.068(1) -0.0027(3) 0.0302(6) 0.0128(3) N(l) 4e 0.1634(8) 0.1610(4) 0.9286(7) 0.078(3) 0.068(3) 0.068(4) -0.005(3) 0.030(3) -0.009(3) N(2) 4e 0.2334(7) 0.0346(3) 0.8287(5) 0.069(3) 0.071(3) 0.048(3) -0.001(2) 0.013(2) -0.002(2) C(l) 4e 0.1830(8) 0.1230(5) 0.7971(7) 0.061(3) 0.063(4) 0.076(4) -0.014(3) 0.022(3) -0.008(3) C(2) 4e 0.1993(8) 0.0968(4) 1.0414(7) 0.058(3) 0.073(4) 0.054(4) -0.007(3) 0.015(3) -0.007(3) C(3) 4e 0.192(1) 0.0981(6) 1.1888(8) 0.083(4) 0.094(5) 0.054(4) -0.013(4) 0.023(3) -0.006(4) C(4) 4e 0.233(1) 0.0210(8) 1.269(1) 0.079(5) 0.146(8) 0.059(5) -0.019(5) 0.018(3) -0.002(5) C(5) 4e 0.285(1) -0.0654(6) 1.214(1) 0.083(5) 0.124(7) 0.081(5) -0.015(4) 0.016(4) 0.037(5) C(6) 4e 0.288(1) -0.0694(5) 1.0606(9) 0.080(4) 0.070(4) 0.080(5) -0.008(3) 0.015(4) 0.013(4) C(7) 4e 0.2431(8) 0.0131(5) 0.9794(7) 0.061(3) 0.087(4) 0.062(4) -0.012(3) 0.023(3) -0.002(3) C(8) 4e 0.098(1) 0.2569(6) 0.9352(9) 0.092(5) 0.078(5) 0.099(5) -0.001(4) 0.034(4) -0.014(4) C(9) 4e 0.256(1) -0.0361(5) 0.7206(9) 0.091(5) 0.076(4) 0.075(5) 0.009(3) 0.036(4) -0.003(4) Acknowledgments. The authors wish to acknowledge the purchase of CAD4 diffractometer under. Grand DPT/TBAG1 of The Scientific and Technical Research Concil of Turkey.