Z. Anorg. Allg. Chem. 2013 · © WILEY-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 · ISSN 0044–2313

SUPPORTING INFORMATION

Title: Polynitro Containing Energetic Materials based on Carbonyldiisocyanate and 2,2-Dinitropropane-1,3-diol

Author(s): T. M. Klapötke, B. Krumm, S. F. Rest, M. Sućeska

Ref. No.: Z201300563

Polynitro containing energetic materials based on carbonyldiisocyanate and 2,2-

dinitropropane-1,3-diol

Thomas M. Klapötke*,[a]

Burkhard Krumm,[a]

Sebastian F. Rest[a]

and Muhamed Sućeska#

Supplementary information

Selected weak improper hydrogen bonds for compound 1–3.

The hydrogen atoms were located in a difference Fourier map and placed with a C–H distance

of 0.99 Å for CH2 groups.

Table 1: Hydrogen bonds of bis(2,2,2-trinitroethyl) carbonyl-N,N-dicarbamate (1)

symmetry operation distances [Å] und angels [°] i –1+x, y, z H2A–C2 0.991(3) ii –1+x, 1+y, z H2B–C2 0.990(4) iii 1+x, –1+y, z H6A–C6 0.990(3) iv 1+x, y, z H6B–C6 0.990(3) v 1–x, 1–y, –z H9A–C9 0.989(3) vi 2–x, 1–y, –z H13B–C13 0.991(2) vii x, –1+y, z H16A–C16 0.990(4) viii x, 1+y, z H16B–C16 0.990(4) H20–N4 0.74(4) H20A–C20 0.991(4) H20B–C20 0.990(3) H22–N12 0.75(4) H23–N13 0.83(3) H23A–C23 0.990(2) H23B–C23 0.990(3) H25–N21 0.83(3) H26–N28 0.67(3) H27A–C27 0.990(5) H27B–C27 0,991(4) H2AO27 2.569(2) H2BO20 2.497(4) H6AO46 2.553(3) H6BO25(iv) 2.432(2) H9AO10(i) 2.250(2) H13BO17 2.544(2) H13BO18 2.551(3) H16AO43(v) 2.605(3) H16BO61(ii) 2.238(4) H20O60 2.23(4) H20AO63(viii) 2.444(5) H20BO59(viii) 571(2) H22O1 2.60(3) H23O32(v) 2.35(3) H23O43 2.51(4) H23AO22(v) 2.454(3) H23AO37(vii) 2.681(3) H23BO44(vii) 2.620(2) H25O26 2.14(3) H26O9(vi) 2.27(3) H27AO42(iii) 2.618(3) H27BO33(iii) 2.555(2) C2O20 3.362(6) C2O27 3.409(3) C6O25(iv) 3.173(4)

C6O46 3.326(5) C9O10(i) 3.230(3) C13O17 3.494(3) C13O18 2.971(5) C16O43(v) 3.514(5) C16O61(ii) 3.162(5) C20O59(viii) 3.469(3) N4O60 2.908(3) C20O63(viii) 3.407(6) N12O1 3.083(3) N13O32(v) 3.136(5) N13O43 3.032(3) C23O22(v) 3.182(4) C23O37(vii) 3.493(4) C23O44(vii) 3.486(3) N21O26 2.941(3) N28O9(vi) 2.893(3) C27O42(iii) 3.365(6) C27O33(iii) 3.348(5) C2–H2AO27 142.6(2) C2–H2BO20 145.8(2) C6–H6AO46 143.9(2) C6–H6BO25(iv) 131.2(2) C9–H9AO10(i) 170.7(2) C13–H13BO17 160.6(2) C13–H13BO18 105.4(2) C16–H16AO43(v) 152.6(2) C16–H16BO61(ii) 154.6(2) N4–H20O60 152(5) C20–H20AO63(viii) 163.8(2) C20–H20BO59(viii) 150.8(2) N12–H22O1 125(3) N13–H23O32(v) 133(3) N13–H23O43 139(3) C23–H23AO22(v) 130.0(2) C23–H23AO37(vii) 147.4(2) C23–H23BO44(vii) 146.1(2) N21–H25O26 156(4) N28–H26O9(vi) 156(4) C27–H27AO42(iii) 132.3(2) C27–H27BO33(iii) 136.9(2)

Table 2: Hydrogen bonds of bis(2-fluoro-2,2-diinitroethyl) carbonyl-N,N-dicarbamate (2)

symmetry operation distances [Å] und angels [°] i –x, 1–y, 1–z H2–N4 0.76(4) ii –1+x, y, z H2A–C2 0.990(3) iii 2–x, 2–y, 2–z H2B–C2 0.989(3) iv 1–x, 1–y, 1–z H6A–C6 0.990(3) v x, y, 1+z H6B–C6 0.990(3) H2O7(iii) 2.10(4) H2AO6(ii) 2.467(2) H2BO11(v) 2.531(3) H6AO3(i) 2.571(3) H6BO10(iv) 2.605(3) C2O6(ii) 3.455(4) C2O11(v) 3.361(4) C6O3(i) 3.420(4) C6O10(iv) 3.481(4) N4O7(iii) 3.847(4) C2–H2AO6(ii) 176.7(2) C2–H2BO11(v) 141.4(2) C6–H6AO3(i) 144.8(2) C6–H6BO10(iv) 147.5(2) N4–H2O7(iii) 167(4)

Table 3: Hydrogen bonds of 2,2-dinitropropane-1,3-diyl bis(2,2,2-trinitroethylcarbamate) (3)

symmetry operation distances [Å] und angels [°] i –1+x, y, z H2A–C2 0.990(2) ii –x, –y, –z H2B–C2 0.990(2) iii 1–x, –y, –z H3–N4 0.85(3) iv 1+x, y, z H4B–C4 0.990(3) v –x, 1–y, –z H6A–C6 0.990(3) H6B–C6 0.990(3) H8A–C8 0.990(2) H8B–C8 0.990(2) H2AO1(i) 2.469(2) H2AO10(ii) 2.620(3) H2BO14(iii) 2.375(2) H3O15(v) 2.28(3) H4BO7(iii) 2.546(2) H6AO7(iii) 2.451(2) H6BO11(iv) 2.559(2) H8AO4(iii) 2.503(2) H8BO3(ii) 2.595(2) H8BO20(i) 2.490(3) C2O1(i) 3.386(3) C2O10(ii) 3.044(4) C2O14(iii) 3.252(3) N4O15(v) 3.113(3) C4O7(iii) 3.300(4) C6O7(iii) 3.246(4) C6O11(iv) 3.368(3) C8O4(iii) 3.463(3) C8O3(ii) 3.122(3) C8O20(i) 3.438(3) C2–H2AO1(i) 154.1(1) C2–H2AO10(ii) 105.9(2) C2–H2BO14(iii) 147.3(1) N4–H3O15(v) 167(3) C4–H4BO7(iii) 132.8(2) C6–H6AO7(iii) 136.9(2) C6–H6BO11(iv) 138.8(2) C8–H8AO4(iii) 163.1(2) C8–H8BO3(ii) 113.3(2) C8–H8BO20(i) 160.2(2)

Figure 1. Molecular structure of Bis(2,2,2-trinitroethyl) carbonyl-N,N-dicarbamate (1). The

complete asymmetric is displayed.