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Crystal structure of 4,4'-diethynylbiphen-yl.

Tagg T, McAdam CJ, Robinson BH, Simpson J - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The title compound, C16H10, crystallizes with four unique mol-ecules, designated 1-4, in the asymmetric unit of the monoclinic unit cell.None of the mol-ecules is planar, with the benzene rings of mol-ecules 1-4 inclined to one another at angles of 42.41 (4), 24.07 (6), 42.59 (4) and 46.88 (4)°, respectively.In the crystal, weak C-H⋯π(ring) interactions, augmented by even weaker C C-H⋯π(alkyne) contacts, generate a three-dimensional network structure with inter-linked columns of mol-ecules formed along the c-axis direction.

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Affiliation: School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia.

ABSTRACT
The title compound, C16H10, crystallizes with four unique mol-ecules, designated 1-4, in the asymmetric unit of the monoclinic unit cell. None of the mol-ecules is planar, with the benzene rings of mol-ecules 1-4 inclined to one another at angles of 42.41 (4), 24.07 (6), 42.59 (4) and 46.88 (4)°, respectively. In the crystal, weak C-H⋯π(ring) interactions, augmented by even weaker C C-H⋯π(alkyne) contacts, generate a three-dimensional network structure with inter-linked columns of mol-ecules formed along the c-axis direction.

No MeSH data available.


Complementary chains of 1, 3 and 2, 4 mol­ecules extending along the c-axis direction. In this and subsequent figures, C—H⋯π(ring) contacts are drawn as dotted lines with ring centroids shown as coloured spheres.
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fig2: Complementary chains of 1, 3 and 2, 4 mol­ecules extending along the c-axis direction. In this and subsequent figures, C—H⋯π(ring) contacts are drawn as dotted lines with ring centroids shown as coloured spheres.

Mentions: A complementary set of C—H⋯π contacts, involving in one case mol­ecules 1 and 3 and in the second mol­ecules 2 and 4, sandwiches a mol­ecule of 1 between two mol­ecules of 3 and a mol­ecule of 2 between two mol­ecules of 4. These contacts generate infinite chains approximately along the c-axis direction. The two chains lie approximately orthogonal to one another, Fig. 2 ▸. Weak C16′—H16′⋯Cg1 contacts form inversion dimers between two adjacent 1 mol­ecules, Fig. 3 ▸, and dimers also result from C—H⋯π contacts involving both rings of adjacent 2 and 3 mol­ecules, Fig. 4 ▸; both these sets of contacts contribute to the overall packing. In addition to these C—H⋯π(ring) inter­actions, one further set of somewhat unusual contacts is formed, again involving all four mol­ecules in the structure. These are weak C C—H⋯π(alkyne) contacts (Desiraju & Steiner, 1999 ▸) involving the relatively acidic C—H donors of the alkyne substituents. These again involve pairs of mol­ecules with C18—H18⋯C37 C38 and C38′—H38′⋯C17′ C18′ contacts generating one set of zigzag chains along b with an adjacent and complementary zigzag produced by C28—H28⋯C47 C48 and C48′—H48′⋯C27′ C28′ inter­actions, These chains generate layers of mol­ecules in the ac plane, Fig. 5 ▸. The contacts display the classic T shape, found also in the neutron structure of acetyl­ene (McMullan et al., 1992 ▸), but not perfectly so. The Hn8⋯Cn7 distances are consistently slightly shorter [mean of the four distances = 2.77 (3) Å] than the Hn8⋯Cn8 equivalents [mean 2.97 (4) Å]. The mean Hn8⋯C C centroid distance is 2.82 (4) Å and these values all fall well within projected ranges for such contacts (Desiraju & Steiner, 1999 ▸). The overall effect of this plethora of weak inter­actions is to stack mol­ecules into ‘multiple-decker sandwich’ columns, linked together along the c-axis direction, Fig. 6 ▸.


Crystal structure of 4,4'-diethynylbiphen-yl.

Tagg T, McAdam CJ, Robinson BH, Simpson J - Acta Crystallogr E Crystallogr Commun (2015)

Complementary chains of 1, 3 and 2, 4 mol­ecules extending along the c-axis direction. In this and subsequent figures, C—H⋯π(ring) contacts are drawn as dotted lines with ring centroids shown as coloured spheres.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518938&req=5

fig2: Complementary chains of 1, 3 and 2, 4 mol­ecules extending along the c-axis direction. In this and subsequent figures, C—H⋯π(ring) contacts are drawn as dotted lines with ring centroids shown as coloured spheres.
Mentions: A complementary set of C—H⋯π contacts, involving in one case mol­ecules 1 and 3 and in the second mol­ecules 2 and 4, sandwiches a mol­ecule of 1 between two mol­ecules of 3 and a mol­ecule of 2 between two mol­ecules of 4. These contacts generate infinite chains approximately along the c-axis direction. The two chains lie approximately orthogonal to one another, Fig. 2 ▸. Weak C16′—H16′⋯Cg1 contacts form inversion dimers between two adjacent 1 mol­ecules, Fig. 3 ▸, and dimers also result from C—H⋯π contacts involving both rings of adjacent 2 and 3 mol­ecules, Fig. 4 ▸; both these sets of contacts contribute to the overall packing. In addition to these C—H⋯π(ring) inter­actions, one further set of somewhat unusual contacts is formed, again involving all four mol­ecules in the structure. These are weak C C—H⋯π(alkyne) contacts (Desiraju & Steiner, 1999 ▸) involving the relatively acidic C—H donors of the alkyne substituents. These again involve pairs of mol­ecules with C18—H18⋯C37 C38 and C38′—H38′⋯C17′ C18′ contacts generating one set of zigzag chains along b with an adjacent and complementary zigzag produced by C28—H28⋯C47 C48 and C48′—H48′⋯C27′ C28′ inter­actions, These chains generate layers of mol­ecules in the ac plane, Fig. 5 ▸. The contacts display the classic T shape, found also in the neutron structure of acetyl­ene (McMullan et al., 1992 ▸), but not perfectly so. The Hn8⋯Cn7 distances are consistently slightly shorter [mean of the four distances = 2.77 (3) Å] than the Hn8⋯Cn8 equivalents [mean 2.97 (4) Å]. The mean Hn8⋯C C centroid distance is 2.82 (4) Å and these values all fall well within projected ranges for such contacts (Desiraju & Steiner, 1999 ▸). The overall effect of this plethora of weak inter­actions is to stack mol­ecules into ‘multiple-decker sandwich’ columns, linked together along the c-axis direction, Fig. 6 ▸.

Bottom Line: The title compound, C16H10, crystallizes with four unique mol-ecules, designated 1-4, in the asymmetric unit of the monoclinic unit cell.None of the mol-ecules is planar, with the benzene rings of mol-ecules 1-4 inclined to one another at angles of 42.41 (4), 24.07 (6), 42.59 (4) and 46.88 (4)°, respectively.In the crystal, weak C-H⋯π(ring) interactions, augmented by even weaker C C-H⋯π(alkyne) contacts, generate a three-dimensional network structure with inter-linked columns of mol-ecules formed along the c-axis direction.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia.

ABSTRACT
The title compound, C16H10, crystallizes with four unique mol-ecules, designated 1-4, in the asymmetric unit of the monoclinic unit cell. None of the mol-ecules is planar, with the benzene rings of mol-ecules 1-4 inclined to one another at angles of 42.41 (4), 24.07 (6), 42.59 (4) and 46.88 (4)°, respectively. In the crystal, weak C-H⋯π(ring) interactions, augmented by even weaker C C-H⋯π(alkyne) contacts, generate a three-dimensional network structure with inter-linked columns of mol-ecules formed along the c-axis direction.

No MeSH data available.