POLYSULFONYLAMINE: TEIL XLV.¹ KRISTALLUND MOLEKÜLSTRUKTUREN VON N-MESYLHARNSTOFF UND N,N′-DIMESYLHARNSTOFF

Abstract

The crystal and molecular structures of the known compounds MeSO₂‒NH‒C(O)‒NH₂ (1) and MeSO₂‒NH‒C(O)‒NH‒SO₂Me (2) are described and compared with literature data for some related substituted ureas. 1 crystallizes in the monoclinic space group C2/c with (at - 75°C) a = 829.8(2), b = 685.9(2), c = 1903.4(4) pm, β = 99.62(2)° V = 1.0681 nm³, Z = 8. The crystallographic data for 2 (at −90°C) are: monoclinic, space group P2₁ /c, a = 918.6(2), b = 954.5(2), c = 905.7(2) pm, l3 = 98.47(2)° V = 0.7855 nm³, Z = 4. The bond lengths and angles of the urea moiety are for 1: C‒O 123.9, C‒NH₂ 132.8, C‒N(S)H 139.5, N‒S 163.7 pm, N‒C‒N 119.2, O‒C‒NH, 123.7, O‒C‒N(S)H 117.1° for 2: C‒O 121.3, C‒N 137.8 and 138.4, N‒S 165.7 and 165.8 pm, N‒C‒N 112.6, O‒C‒N 123.7° (2X). The molecules of 1 display anti-conformation with an intramolecular hydrogen bond N‒H O(S); in the crystal packing, they are associated into ribbons by two intermolecular hydrogen bonds N‒H ··· O(C). The molecules of 2 have a syn-syn-conformation; they form dimers by two symmetry-equivalent hydrogen bonds N‒H ··· O(S), the dimers being interconnected into chains by a hydrogen bond of the type N‒H ··· O(C).

Key Words:

• N-Mesylurea; N,N′-dimesylurea
• X-ray crystallography
• crystal and molecular structures
• conformations
• hydrogen bonds.