The functionalization of N-(benzo[d]thiazol-2-yl)benzamide with a nitro (NO₂) substituent influences the solid-state arrangement, absorption and fluorescence properties of these compounds. Each of these compounds crystallised in a different crystal system or space group, namely a monoclinic crystal system with P2₁/n and C2/c space groups for o-NO₂ and m-NO₂ derivatives, respectively, and an orthorhombic crystal system (Pbcn space group) for p-NO₂ derivative. The o-NO₂ substituent with intrinsic steric hindrance engendered a distorted geometry. Conversely, the m-NO₂ derivate displayed the most planar geometry among the analogues. The solid-state architectures of these compounds were dominated by the N−H···N and C−H···O intermolecular hydrogen bonds and were further stabilised by other weak interactions. The dimer synthons of the compounds were established via a pair of N−H···N hydrogen bonds. These findings were corroborated by a Hirshfeld surface analysis and two-dimensional (2D) fingerprint plot. The interaction energies within the crystal packing were calculated (CE-B3LYP/6-31G(d,p)) and the energy frameworks were modelled by CrystalExplorer17.5. The highly distorted o-NO₂ congener synthon relied mainly on the dispersion forces, which included π–π interactions compared to the electrostatic attractions found in m-NO₂. Besides, the latter possesses an elevated asphericity character, portraying a marked directionality in the crystal array. The electrostatic and dispersion forces were regarded as the dominant factors in stabilising the crystal packing.

中文翻译：

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N-（苯并[d]噻唑-2-基）-o / m /对硝基苯甲酰胺的位置异构现象的认识：晶体结构，Hirshfeld表面分析和相互作用能

具有硝基（NO ₂）取代基的N-（苯并[ d ]噻唑-2-基）苯甲酰胺的官能化影响这些化合物的固态排列，吸收和荧光性质。这些化合物各自在不同的晶体系统或空间组中结晶，即分别具有用于o -NO ₂和m -NO ₂衍生物的P 2 ₁ / n和C 2 / c空间基团的单斜晶体系统，以及正交晶体。系统（Pbcn空间组）p -NO ₂衍生物。具有固有空间位阻的o -NO ₂取代基引起扭曲的几何形状。相反，m -NO ₂衍生物显示出类似物中最平坦的几何形状。这些化合物的固态结构主要由N-H··N和C·H···O分子间氢键主导，并通过其他弱相互作用进一步稳定。化合物的二聚体合成子通过一对NH···N氢键建立。这些发现通过Hirshfeld表面分析和二维（2D）指纹图得到了证实。计算了晶体堆积内部的相互作用能（CE-B3LYP / 6-31G（d，p）），并通过CrystalExplorer17.5对能量构架进行了建模。高度扭曲o- NO ₂同源合成子主要依赖于分散力，与m- NO _2中的静电引力相比，它包括π-π相互作用。此外，后者具有提高的非球面性，在晶体阵列中表现出明显的方向性。静电力和分散力被认为是稳定晶体堆积的主要因素。