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Crystal structure of ( E )-4-hy ­ droxy- N ′ -(3-meth ­ oxy ­ benzyl ­ idene)benzohydrazide 1

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ABSTRACT

The title compound, C15H14N2O3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit that differ in the orientation of the 3-meth­oxy­phenyl group with respect to the methyl­idenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02 (10) and 29.30 (9)° in mol­ecules A and B, respectively. In mol­ecule A, the meth­oxy group is twisted slightly relative to its bound benzene ring, with a Cmeth­yl—O—C—C torsion angle of 14.2 (3)°, whereas it is almost co-planar in mol­ecule B, where the corresponding angle is −2.4 (3)°. In the crystal, the mol­ecules are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, as well as by weak C—H⋯O inter­actions, forming sheets parallel to the bc plane. The N—H⋯O hydrogen bond and weak C—H⋯O inter­action link different mol­ecules (A⋯B) whereas both O—H⋯N and O—H⋯O hydrogen bonds link like mol­ecules (A⋯A) and (B⋯B). Pairs of inversion-related B mol­ecules are stacked approximately along the a axis by π–π inter­actions in which the distance between the centroids of the 3-meth­oxy­phenyl rings is 3.5388 (12) Å. The B mol­ecules also participate in weak C—H⋯π inter­actions between the 4-hy­droxy­phenyl and the 3-meth­oxy­phenyl rings.

No MeSH data available.


Mol­ecular packing of (I) linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds drawn as dotted lines.
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fig2: Mol­ecular packing of (I) linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds drawn as dotted lines.

Mentions: In the crystal (Fig. 2 ▸), the mol­ecules are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, as well as by weak C—H⋯O inter­actions (Table 1 ▸), into sheets parallel to the bc plane. The N1A—H1A⋯O2Bi and N1B—H1B⋯O3Aii hydrogen bonds and C13B—H13B⋯O1Aiv inter­actions link non-equivalent mol­ecules (A⋯B) whereas the O2A—H2A⋯N2Aiii and O2A—H2A⋯O1Aiii hydrogen bonds link equivalent A mol­ecules, and O2B—H2B⋯N2Bii and O2B—H2B⋯O1Bii hydrogen bonds link equivalent B mol­ecules. Stacking of planes of mol­ecules in the a-axis direction involves π–π inter­actions between B mol­ecules with Cg⋯Cgvi distance of 3.5388 (12) Å. A weak C—H⋯π inter­action (C3B—H3B⋯Cgv) between the 4-hy­droxy­phenyl ring and the 3-meth­oxy­phenyl ring of symmetry-related B mol­ecules is also present (Fig. 3 ▸, Table 1 ▸) [symmetry codes: (i) −x, 1 − y, 1 − z; (ii) x,  − y, − + z; (iii) x,  − y, − + z; (iv) x, 1 + y, z; (v) −x, − + y,  − z; (vi) 1 − x, 2 − y, 2 − z; Cg is the centroid of the C9B–C14B ring].


Crystal structure of ( E )-4-hy ­ droxy- N ′ -(3-meth ­ oxy ­ benzyl ­ idene)benzohydrazide 1
Mol­ecular packing of (I) linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds drawn as dotted lines.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
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getmorefigures.php?uid=PMC5120720&req=5

fig2: Mol­ecular packing of (I) linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds drawn as dotted lines.
Mentions: In the crystal (Fig. 2 ▸), the mol­ecules are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, as well as by weak C—H⋯O inter­actions (Table 1 ▸), into sheets parallel to the bc plane. The N1A—H1A⋯O2Bi and N1B—H1B⋯O3Aii hydrogen bonds and C13B—H13B⋯O1Aiv inter­actions link non-equivalent mol­ecules (A⋯B) whereas the O2A—H2A⋯N2Aiii and O2A—H2A⋯O1Aiii hydrogen bonds link equivalent A mol­ecules, and O2B—H2B⋯N2Bii and O2B—H2B⋯O1Bii hydrogen bonds link equivalent B mol­ecules. Stacking of planes of mol­ecules in the a-axis direction involves π–π inter­actions between B mol­ecules with Cg⋯Cgvi distance of 3.5388 (12) Å. A weak C—H⋯π inter­action (C3B—H3B⋯Cgv) between the 4-hy­droxy­phenyl ring and the 3-meth­oxy­phenyl ring of symmetry-related B mol­ecules is also present (Fig. 3 ▸, Table 1 ▸) [symmetry codes: (i) −x, 1 − y, 1 − z; (ii) x,  − y, − + z; (iii) x,  − y, − + z; (iv) x, 1 + y, z; (v) −x, − + y,  − z; (vi) 1 − x, 2 − y, 2 − z; Cg is the centroid of the C9B–C14B ring].

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title compound, C15H14N2O3, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit that differ in the orientation of the 3-meth­oxy­phenyl group with respect to the methyl­idenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02 (10) and 29.30 (9)° in mol­ecules A and B, respectively. In mol­ecule A, the meth­oxy group is twisted slightly relative to its bound benzene ring, with a Cmeth­yl—O—C—C torsion angle of 14.2 (3)°, whereas it is almost co-planar in mol­ecule B, where the corresponding angle is −2.4 (3)°. In the crystal, the mol­ecules are linked by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, as well as by weak C—H⋯O inter­actions, forming sheets parallel to the bc plane. The N—H⋯O hydrogen bond and weak C—H⋯O inter­action link different mol­ecules (A⋯B) whereas both O—H⋯N and O—H⋯O hydrogen bonds link like mol­ecules (A⋯A) and (B⋯B). Pairs of inversion-related B mol­ecules are stacked approximately along the a axis by π–π inter­actions in which the distance between the centroids of the 3-meth­oxy­phenyl rings is 3.5388 (12) Å. The B mol­ecules also participate in weak C—H⋯π inter­actions between the 4-hy­droxy­phenyl and the 3-meth­oxy­phenyl rings.

No MeSH data available.