Hossain M B, Wang J L, van der Helm D, Magarian R A, Griffin M T, Day B W
Department of Chemistry and Biochemistry, University of Oklahoma, Norman 73019.
Acta Crystallogr B. 1991 Aug 1;47 ( Pt 4):511-21. doi: 10.1107/s0108768191000976.
The pure antiestrogenic activity of compound (1) gave the impetus to synthesize a series of its derivatives (2)-(4). Structural features of these compounds are compared. Compound (1): 1,1-dichloro-cis-2,3-diphenylcyclopropane, C15H12Cl2, Mr = 263.2, orthorhombic, Pbca, a = 19.627 (7), b = 19.460 (6), c = 6.670 (2) A, V = 2547.5 A3, Z = 8, D chi = 1.372 g cm-3, lambda (MoK alpha) = 0.71069 A, mu (Mo K alpha) = 4.3 cm-1, F(000) = 1088, T = 138 K, R = 0.026 for 1923 observed reflections. Compound (2): 1,1-dichloro-cis-2,3-bis(4-methoxyphenyl)cyclopropane, C17H16Cl2O2, Mr = 323.2, monoclinic, P2(1)/C, a = 16.540(1), b = 7.4749(7), c = 12.333 (3) A, beta = 91.53 (2) degrees, V = 1524.2 A3, Z = 4, D chi = 1.408 g cm-3, lambda (Cu K alpha) = 1.54178 A, mu (Cu K alpha) = 37.0 cm-1, F(000) = 672, T = 163 K, R = 0.031 for 2919 observed reflections. Compound (3): 1,1-dichloro-cis-2-(4-benzyloxyphenyl)-3-phenylcyclopropane, C22H18Cl2O, Mr = 369.3, monoclinic, P2(1)/alpha, a = 21.064 (3), b = 14.749 (2), c = 5.8222 (8) A, beta = 95.48 (2) degrees, V = 1800.5 A3, Z = 4, D chi = 1.362 g cm-3, lambda (Cu K alpha) = 1.54178 A, mu (CuK alpha) = 31.5 cm-1, F(000) = 768, T = 163 K, R = 0.032 for 3256 observed reflections. Compound (4): 1,1-dichloro-trans-2-(4-acetoxyphenyl)-3-phenylcyclopropane, C17H14Cl2O2, Mr = 321.2, monoclinic, P2(1)/n, a = 16.555 (4), b = 12.297 (2), c = 7.439 (1) A, beta = 98.31 (2) degrees, V = 1498.5 A3, Z = 4, D chi = 1.423 g cm-3, lambda (Mo K alpha) = 0.71069 A, mu (Mo K alpha) = 3.8 cm-1, F(000) = 664, T = 163 K, R = 0.034 for 2474 observed reflections. The crystal structure determinations show that the relative conformation of the two aryl rings in all four structures are quite similar. In this conformation one of the phenyl rings is in a bisecting position with respect to the cyclopropane ring, while the other is in a perpendicular position. In each of the four molecules the cyclopropane ring shows significant bond-length asymmetry with d[C(2)-C(3)] greater than d [C(1)-C(3)] greater than d[C(1)-C(2)].(ABSTRACT TRUNCATED AT 400 WORDS)
化合物（1）的纯抗雌激素活性推动了一系列其衍生物（2）-（4）的合成。对这些化合物的结构特征进行了比较。化合物（1）：1,1 - 二氯 - 顺式 - 2,3 - 二苯基环丙烷，C15H12Cl2，Mr = 263.2，正交晶系，Pbca，a = 19.627（7），b = 19.460（6），c = 6.670（2）Å，V = 2547.5 Å3，Z = 8，Dχ = 1.372 g cm-3，λ（MoKα） = 0.71069 Å，μ（Mo Kα） = 4.3 cm-1，F(000) = 1088，T = 138 K，对于1923个观测反射，R = 0.026。化合物（2）：1,1 - 二氯 - 顺式 - 2,3 - 双（4 - 甲氧基苯基）环丙烷，C17H16Cl2O2，Mr = 323.2，单斜晶系，P2(1)/C，a = 16.540(1)，b = 7.4749(7)，c = 12.333（3）Å，β = 91.53（2）°，V = 1524.2 Å3，Z = 4，Dχ = 1.408 g cm-3，λ（Cu Kα） = 1.54178 Å，μ（Cu Kα） = 37.0 cm-1，F(000) = 672，T = 163 K，对于2919个观测反射，R = 0.031。化合物（3）：1,1 - 二氯 - 顺式 - 2 - （4 - 苄氧基苯基）- 3 - 苯基环丙烷，C22H18Cl2O，Mr = 369.3，单斜晶系，P2(1)/α，a = 21.064（3），b = 14.749（2），c = 5.8222（8）Å，β = 95.48（2）°，V = 1800.5 Å3，Z = 4，Dχ = 1.362 g cm-3，λ（Cu Kα） = 1.54178 Å，μ（CuKα） = 31.5 cm-1，F(000) = 768，T = 163 K，对于3256个观测反射，R = 0.032。化合物（4）：1,1 - 二氯 - 反式 - 2 - （4 - 乙酰氧基苯基）- 3 - 苯基环丙烷，C17H14Cl2O2，Mr = 321.2，单斜晶系，P2(1)/n，a = 16.555（4），b = 12.297（2），c = 7.439（1）Å，β = 98.31（2）°，V = 1498.5 Å3，Z = 4，Dχ = 1.423 g cm-3，λ（Mo Kα） = 0.71069 Å，μ（Mo Kα） = 3.8 cm-1，F(000) = 664，T = 163 K，对于2474个观测反射，R = 0.034。晶体结构测定表明，所有四种结构中两个芳环的相对构象非常相似。在这种构象中，其中一个苯环相对于环丙烷环处于平分位置，而另一个处于垂直位置。在这四个分子中的每一个中，环丙烷环都显示出明显的键长不对称性，d[C(2)-C(3)]大于d [C(1)-C(3)]大于d[C(1)-C(2)]。（摘要截断于400字）
