organic compounds
1,1,4,7,7-Pentamethyldiethylenetriammonium trinitrate
aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
*Correspondence e-mail: houda_marouani@voila.fr
In the title compound, C9H26N33+·3NO3−, the triprotonated 1,1,4,7,7-pentamethyldiethylenetriamine molecules are linked to the nitrate anions by multiple bifurcated N—H⋯(O,O) and weak C—H⋯O hydrogen bonds. The organic cation is characterized by N—C—C—N torsion angles of −176.2 (2) and 176.6 (2)°.
CCDC reference: 982611
Related literature
For related structures, see: Marouani et al. (2012); Gatfaoui et al. (2013); Kefi et al. (2013); Ben Slimane & Smirani (2008); Morawitz et al. (2005). For a discussion on hydrogen bonding, see: Brown (1976); Blessing (1986).
Experimental
Crystal data
|
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).
Supporting information
CCDC reference: 982611
10.1107/S1600536814001469/bh2492sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001469/bh2492Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001469/bh2492Isup3.cml
An aqueous solution containing 3 mmol of HNO3 in 10 ml of water was added to 1 mmol of 1,1,4,7,7-pentamethylethylenetriamine in 10 ml of water. The resulting solution was stirred for 15 min. and then left to stand at room temperature. Colourless single crystals of the title compound were obtained after some days.
The hydrogen atoms bonded to N1, N2 and N3 were located in a difference map and were allowed to refine (coordinates and isotropic displacement parameters). The rest of the H atoms were treated as riding, with C—H = 0.97 Å (methylene) or 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C).
1,1,4,7,7-Pentamethyldiethylenetriamine is an amine catalyst primarily used in the production of spray polyurethane foam (SPF). It is classified as tertiary and has basic and nucleophilic properties. In this work, we report the preparation and the structural investigation of a new organic nitrate, C9H26N3(NO3)3.
The
of the title salt consists of three nitrate anions and one 1,1,4,7,7-pentamethylethylenetriammonium trication (Fig. 1). The organic cations are connected to the nitrate anions through multiple bifurcated N—H···O and weak C—H···O hydrogen bonds, with donor-acceptor distances varying between 2.749 (3) and 3.386 (4) Å [d (O···O) > 2.73 Å; Brown, 1976; Blessing, 1986. See Table 1 and Fig. 2).Nitrate anions are distributed in the (b,c) plane and are interconnected through the organic cations which extend in the direction of the c axis. Geometrical characteristics of the three independent nitrate anions are slightly different. The distance N5—O6 is notably the shortest, 1.204 (3) Å, because O6 is applied in only one hydrogen bond (Table 1) at the same time as N5—O5 distance is much larger, 1.248 (3) Å, because O5 is involved in three hydrogen bonds. These geometrical features have also been noticed in other crystal structures (Marouani et al., 2012; Gatfaoui et al., 2013; Kefi et al., 2013).
Each organic entity is bounded to six different nitrate anions through fifteen N—H···O and C—H···O hydrogen bonds forming a two dimensional network. Examination of the 1,1,4,7,7-pentamethylethylenetriammonium cation shows that the bond distances and angles show no significant difference from those obtained in other structures involving the same organic groups (Morawitz et al., 2005; Ben Slimane & Smirani, 2008). The crystal cohesion and stability are ensured by electrostatic and van der Waals interactions which, together with N—H···O and C—H···O hydrogen bonds, build up a two-dimensional network.
For related structures, see: Marouani et al. (2012); Gatfaoui et al. (2013); Kefi et al. (2013); Ben Slimane & Smirani (2008); Morawitz et al. (2005). For a discussion on hydrogen bonding, see: Brown (1976); Blessing (1986).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell
CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).Fig. 1. An ORTEP view of the asymmetric unit of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. Hydrogen bonds are shown as dotted lines. | |
Fig. 2. Projection of the title compound along the a axis. The H atoms not involved in H-bonding are omitted. |
C9H26N6O9 | Z = 2 |
Mr = 362.36 | F(000) = 388 |
Triclinic, P1 | Dx = 1.359 Mg m−3 |
Hall symbol: -P 1 | Ag Kα radiation, λ = 0.56083 Å |
a = 5.964 (2) Å | Cell parameters from 25 reflections |
b = 7.018 (1) Å | θ = 9–11° |
c = 21.688 (2) Å | µ = 0.07 mm−1 |
α = 91.90 (2)° | T = 293 K |
β = 90.60 (2)° | Prism, colourless |
γ = 102.45 (3)° | 0.40 × 0.35 × 0.30 mm |
V = 885.8 (3) Å3 |
Enraf–Nonius CAD4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 19.5°, θmin = 2.2° |
Graphite monochromator | h = −7→7 |
non–profiled ω scans | k = −8→8 |
3582 measured reflections | l = −2→25 |
3128 independent reflections | 2 standard reflections every 120 min |
2125 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.184 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0789P)2 + 0.6513P] where P = (Fo2 + 2Fc2)/3 |
3128 reflections | (Δ/σ)max < 0.001 |
234 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
0 constraints |
C9H26N6O9 | γ = 102.45 (3)° |
Mr = 362.36 | V = 885.8 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.964 (2) Å | Ag Kα radiation, λ = 0.56083 Å |
b = 7.018 (1) Å | µ = 0.07 mm−1 |
c = 21.688 (2) Å | T = 293 K |
α = 91.90 (2)° | 0.40 × 0.35 × 0.30 mm |
β = 90.60 (2)° |
Enraf–Nonius CAD4 diffractometer | Rint = 0.030 |
3582 measured reflections | 2 standard reflections every 120 min |
3128 independent reflections | intensity decay: 2% |
2125 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.184 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.29 e Å−3 |
3128 reflections | Δρmin = −0.24 e Å−3 |
234 parameters |
x | y | z | Uiso*/Ueq | ||
N1 | 0.4083 (4) | 0.2269 (4) | 0.40433 (11) | 0.0411 (6) | |
N2 | 0.5838 (4) | 0.0897 (3) | 0.24407 (10) | 0.0344 (5) | |
N3 | 0.3516 (4) | 0.2565 (4) | 0.09611 (11) | 0.0388 (6) | |
N4 | −0.0530 (5) | 0.8384 (4) | 0.08493 (13) | 0.0548 (7) | |
N5 | 0.9855 (5) | 0.5138 (4) | 0.24709 (13) | 0.0519 (7) | |
N6 | 0.0036 (5) | 0.8141 (4) | 0.41497 (14) | 0.0601 (7) | |
O1 | −0.0634 (4) | 0.9934 (4) | 0.11371 (13) | 0.0711 (7) | |
O2 | −0.2111 (5) | 0.6968 (5) | 0.08600 (17) | 0.1129 (12) | |
O3 | 0.1225 (5) | 0.8341 (4) | 0.05677 (15) | 0.0926 (10) | |
O4 | 0.7958 (5) | 0.5372 (4) | 0.26319 (15) | 0.0839 (9) | |
O5 | 1.0059 (4) | 0.3412 (3) | 0.23999 (13) | 0.0675 (7) | |
O6 | 1.1418 (5) | 0.6488 (5) | 0.23730 (18) | 0.1128 (12) | |
O7 | −0.0504 (5) | 0.9697 (5) | 0.40675 (18) | 0.1064 (11) | |
O8 | −0.1275 (6) | 0.6643 (5) | 0.4269 (2) | 0.1306 (15) | |
O9 | 0.2109 (4) | 0.8175 (4) | 0.41010 (15) | 0.0816 (8) | |
C1 | 0.5618 (5) | 0.1954 (4) | 0.35333 (13) | 0.0433 (7) | |
H1A | 0.6433 | 0.0955 | 0.3644 | 0.052* | |
H1B | 0.6746 | 0.3152 | 0.3474 | 0.052* | |
C2 | 0.4284 (4) | 0.1337 (4) | 0.29386 (13) | 0.0411 (7) | |
H2A | 0.3090 | 0.0186 | 0.3003 | 0.049* | |
H2B | 0.3553 | 0.2373 | 0.2812 | 0.049* | |
C3 | 0.4709 (5) | 0.0753 (4) | 0.18173 (13) | 0.0395 (7) | |
H3A | 0.3187 | −0.0081 | 0.1834 | 0.047* | |
H3B | 0.5593 | 0.0157 | 0.1524 | 0.047* | |
C4 | 0.4516 (5) | 0.2739 (4) | 0.15978 (13) | 0.0424 (7) | |
H4A | 0.3550 | 0.3304 | 0.1875 | 0.051* | |
H4B | 0.6026 | 0.3600 | 0.1603 | 0.051* | |
C5 | 0.5362 (6) | 0.2467 (5) | 0.46408 (14) | 0.0561 (8) | |
H5A | 0.6040 | 0.1357 | 0.4688 | 0.084* | |
H5B | 0.4326 | 0.2537 | 0.4972 | 0.084* | |
H5C | 0.6548 | 0.3636 | 0.4649 | 0.084* | |
C6 | 0.3009 (7) | 0.3951 (6) | 0.39551 (19) | 0.0763 (12) | |
H6A | 0.4184 | 0.5104 | 0.3903 | 0.114* | |
H6B | 0.2120 | 0.4134 | 0.4310 | 0.114* | |
H6C | 0.2027 | 0.3708 | 0.3595 | 0.114* | |
C7 | 0.6704 (5) | −0.0917 (4) | 0.25532 (15) | 0.0485 (8) | |
H7A | 0.5432 | −0.2019 | 0.2553 | 0.073* | |
H7B | 0.7494 | −0.0783 | 0.2945 | 0.073* | |
H7C | 0.7740 | −0.1109 | 0.2233 | 0.073* | |
C8 | 0.2505 (6) | 0.4277 (5) | 0.08285 (16) | 0.0559 (8) | |
H8A | 0.3696 | 0.5443 | 0.0843 | 0.084* | |
H8B | 0.1376 | 0.4393 | 0.1131 | 0.084* | |
H8C | 0.1794 | 0.4099 | 0.0426 | 0.084* | |
C9 | 0.5213 (6) | 0.2317 (5) | 0.04887 (15) | 0.0597 (9) | |
H9A | 0.6439 | 0.3457 | 0.0496 | 0.090* | |
H9B | 0.4479 | 0.2142 | 0.0089 | 0.090* | |
H9C | 0.5821 | 0.1193 | 0.0575 | 0.090* | |
H1 | 0.304 (6) | 0.114 (5) | 0.4038 (14) | 0.051 (9)* | |
H2 | 0.701 (5) | 0.188 (4) | 0.2414 (12) | 0.036 (8)* | |
H3 | 0.247 (6) | 0.148 (5) | 0.0925 (14) | 0.051 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0408 (13) | 0.0376 (13) | 0.0435 (14) | 0.0050 (11) | 0.0083 (11) | −0.0007 (10) |
N2 | 0.0270 (11) | 0.0358 (13) | 0.0420 (13) | 0.0093 (10) | 0.0055 (10) | 0.0069 (10) |
N3 | 0.0332 (12) | 0.0402 (14) | 0.0420 (14) | 0.0044 (10) | 0.0009 (10) | 0.0080 (10) |
N4 | 0.0470 (16) | 0.0527 (17) | 0.0597 (17) | −0.0003 (13) | −0.0091 (14) | 0.0049 (13) |
N5 | 0.0464 (16) | 0.0452 (16) | 0.0606 (17) | 0.0017 (13) | −0.0009 (13) | 0.0042 (12) |
N6 | 0.0506 (17) | 0.0542 (18) | 0.073 (2) | 0.0052 (14) | 0.0031 (14) | 0.0033 (14) |
O1 | 0.0511 (14) | 0.0646 (16) | 0.097 (2) | 0.0111 (12) | 0.0169 (13) | −0.0059 (14) |
O2 | 0.088 (2) | 0.092 (2) | 0.129 (3) | −0.0453 (18) | −0.0175 (19) | 0.0045 (19) |
O3 | 0.083 (2) | 0.087 (2) | 0.110 (2) | 0.0251 (16) | 0.0385 (18) | −0.0092 (17) |
O4 | 0.0724 (18) | 0.0576 (16) | 0.131 (2) | 0.0310 (13) | 0.0247 (17) | 0.0134 (15) |
O5 | 0.0396 (12) | 0.0509 (14) | 0.114 (2) | 0.0139 (10) | 0.0117 (12) | 0.0000 (13) |
O6 | 0.084 (2) | 0.074 (2) | 0.158 (3) | −0.0324 (17) | 0.019 (2) | 0.003 (2) |
O7 | 0.083 (2) | 0.082 (2) | 0.166 (3) | 0.0474 (17) | −0.029 (2) | −0.004 (2) |
O8 | 0.099 (2) | 0.079 (2) | 0.192 (4) | −0.0311 (19) | 0.061 (3) | 0.003 (2) |
O9 | 0.0541 (16) | 0.0658 (17) | 0.127 (2) | 0.0163 (12) | 0.0059 (15) | 0.0145 (16) |
C1 | 0.0335 (14) | 0.0544 (18) | 0.0443 (17) | 0.0141 (13) | 0.0033 (12) | 0.0036 (13) |
C2 | 0.0303 (14) | 0.0530 (17) | 0.0434 (16) | 0.0157 (12) | 0.0070 (12) | 0.0056 (13) |
C3 | 0.0363 (14) | 0.0413 (16) | 0.0421 (16) | 0.0109 (12) | 0.0004 (12) | 0.0031 (12) |
C4 | 0.0443 (16) | 0.0460 (16) | 0.0398 (16) | 0.0161 (13) | 0.0021 (13) | 0.0025 (12) |
C5 | 0.072 (2) | 0.0535 (19) | 0.0418 (18) | 0.0111 (16) | 0.0008 (16) | 0.0014 (14) |
C6 | 0.078 (3) | 0.086 (3) | 0.078 (3) | 0.052 (2) | −0.011 (2) | −0.019 (2) |
C7 | 0.0501 (17) | 0.0454 (17) | 0.0566 (19) | 0.0240 (14) | 0.0011 (14) | 0.0076 (14) |
C8 | 0.0538 (19) | 0.062 (2) | 0.059 (2) | 0.0257 (16) | 0.0027 (16) | 0.0186 (16) |
C9 | 0.067 (2) | 0.070 (2) | 0.0472 (19) | 0.0258 (18) | 0.0158 (16) | 0.0065 (16) |
N1—C6 | 1.475 (4) | C1—H1B | 0.9700 |
N1—C5 | 1.484 (4) | C2—H2A | 0.9700 |
N1—C1 | 1.484 (3) | C2—H2B | 0.9700 |
N1—H1 | 0.90 (3) | C3—C4 | 1.515 (4) |
N2—C3 | 1.495 (3) | C3—H3A | 0.9700 |
N2—C2 | 1.498 (3) | C3—H3B | 0.9700 |
N2—C7 | 1.499 (3) | C4—H4A | 0.9700 |
N2—H2 | 0.87 (3) | C4—H4B | 0.9700 |
N3—C9 | 1.479 (4) | C5—H5A | 0.9600 |
N3—C4 | 1.489 (4) | C5—H5B | 0.9600 |
N3—C8 | 1.491 (4) | C5—H5C | 0.9600 |
N3—H3 | 0.87 (3) | C6—H6A | 0.9600 |
N4—O2 | 1.214 (4) | C6—H6B | 0.9600 |
N4—O3 | 1.223 (4) | C6—H6C | 0.9600 |
N4—O1 | 1.249 (4) | C7—H7A | 0.9600 |
N5—O6 | 1.204 (3) | C7—H7B | 0.9600 |
N5—O4 | 1.230 (3) | C7—H7C | 0.9600 |
N5—O5 | 1.248 (3) | C8—H8A | 0.9600 |
N6—O8 | 1.205 (4) | C8—H8B | 0.9600 |
N6—O7 | 1.221 (4) | C8—H8C | 0.9600 |
N6—O9 | 1.237 (4) | C9—H9A | 0.9600 |
C1—C2 | 1.509 (4) | C9—H9B | 0.9600 |
C1—H1A | 0.9700 | C9—H9C | 0.9600 |
C6—N1—C5 | 111.1 (3) | C4—C3—H3A | 109.3 |
C6—N1—C1 | 113.2 (3) | N2—C3—H3B | 109.3 |
C5—N1—C1 | 109.8 (2) | C4—C3—H3B | 109.3 |
C6—N1—H1 | 112 (2) | H3A—C3—H3B | 107.9 |
C5—N1—H1 | 108 (2) | N3—C4—C3 | 110.5 (2) |
C1—N1—H1 | 102 (2) | N3—C4—H4A | 109.6 |
C3—N2—C2 | 111.8 (2) | C3—C4—H4A | 109.6 |
C3—N2—C7 | 110.1 (2) | N3—C4—H4B | 109.6 |
C2—N2—C7 | 112.4 (2) | C3—C4—H4B | 109.6 |
C3—N2—H2 | 103.5 (18) | H4A—C4—H4B | 108.1 |
C2—N2—H2 | 109.4 (18) | N1—C5—H5A | 109.5 |
C7—N2—H2 | 109.2 (18) | N1—C5—H5B | 109.5 |
C9—N3—C4 | 112.2 (2) | H5A—C5—H5B | 109.5 |
C9—N3—C8 | 110.5 (2) | N1—C5—H5C | 109.5 |
C4—N3—C8 | 110.9 (2) | H5A—C5—H5C | 109.5 |
C9—N3—H3 | 104 (2) | H5B—C5—H5C | 109.5 |
C4—N3—H3 | 109 (2) | N1—C6—H6A | 109.5 |
C8—N3—H3 | 111 (2) | N1—C6—H6B | 109.5 |
O2—N4—O3 | 121.6 (3) | H6A—C6—H6B | 109.5 |
O2—N4—O1 | 120.7 (3) | N1—C6—H6C | 109.5 |
O3—N4—O1 | 117.7 (3) | H6A—C6—H6C | 109.5 |
O6—N5—O4 | 122.3 (3) | H6B—C6—H6C | 109.5 |
O6—N5—O5 | 121.5 (3) | N2—C7—H7A | 109.5 |
O4—N5—O5 | 116.2 (3) | N2—C7—H7B | 109.5 |
O8—N6—O7 | 125.1 (4) | H7A—C7—H7B | 109.5 |
O8—N6—O9 | 119.9 (3) | N2—C7—H7C | 109.5 |
O7—N6—O9 | 114.9 (3) | H7A—C7—H7C | 109.5 |
N1—C1—C2 | 111.4 (2) | H7B—C7—H7C | 109.5 |
N1—C1—H1A | 109.3 | N3—C8—H8A | 109.5 |
C2—C1—H1A | 109.3 | N3—C8—H8B | 109.5 |
N1—C1—H1B | 109.3 | H8A—C8—H8B | 109.5 |
C2—C1—H1B | 109.3 | N3—C8—H8C | 109.5 |
H1A—C1—H1B | 108.0 | H8A—C8—H8C | 109.5 |
N2—C2—C1 | 110.6 (2) | H8B—C8—H8C | 109.5 |
N2—C2—H2A | 109.5 | N3—C9—H9A | 109.5 |
C1—C2—H2A | 109.5 | N3—C9—H9B | 109.5 |
N2—C2—H2B | 109.5 | H9A—C9—H9B | 109.5 |
C1—C2—H2B | 109.5 | N3—C9—H9C | 109.5 |
H2A—C2—H2B | 108.1 | H9A—C9—H9C | 109.5 |
N2—C3—C4 | 111.7 (2) | H9B—C9—H9C | 109.5 |
N2—C3—H3A | 109.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O9i | 0.90 (3) | 2.04 (3) | 2.868 (4) | 153 (3) |
N1—H1···O7i | 0.90 (3) | 2.14 (3) | 2.937 (4) | 147 (3) |
N2—H2···O5 | 0.87 (3) | 1.90 (3) | 2.749 (3) | 162 (3) |
N2—H2···O4 | 0.87 (3) | 2.42 (3) | 3.134 (4) | 139 (2) |
N3—H3···O1i | 0.87 (3) | 2.00 (3) | 2.789 (4) | 149 (3) |
N3—H3···O3i | 0.87 (3) | 2.28 (3) | 3.073 (4) | 152 (3) |
C1—H1A···O7ii | 0.97 | 2.38 | 3.293 (4) | 156 |
C1—H1B···O4 | 0.97 | 2.45 | 3.232 (4) | 137 |
C2—H2B···O5iii | 0.97 | 2.52 | 3.386 (4) | 149 |
C3—H3B···O1ii | 0.97 | 2.44 | 3.308 (4) | 148 |
C4—H4A···O5iii | 0.97 | 2.40 | 3.301 (4) | 155 |
C5—H5C···O8iv | 0.96 | 2.40 | 3.305 (5) | 156 |
C7—H7A···O6v | 0.96 | 2.42 | 3.295 (4) | 152 |
C8—H8A···O2iv | 0.96 | 2.50 | 3.355 (5) | 149 |
C9—H9A···O2iv | 0.96 | 2.53 | 3.377 (5) | 148 |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y−1, z; (iii) x−1, y, z; (iv) x+1, y, z; (v) x−1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O9i | 0.90 (3) | 2.04 (3) | 2.868 (4) | 153 (3) |
N1—H1···O7i | 0.90 (3) | 2.14 (3) | 2.937 (4) | 147 (3) |
N2—H2···O5 | 0.87 (3) | 1.90 (3) | 2.749 (3) | 162 (3) |
N2—H2···O4 | 0.87 (3) | 2.42 (3) | 3.134 (4) | 139 (2) |
N3—H3···O1i | 0.87 (3) | 2.00 (3) | 2.789 (4) | 149 (3) |
N3—H3···O3i | 0.87 (3) | 2.28 (3) | 3.073 (4) | 152 (3) |
C1—H1A···O7ii | 0.97 | 2.38 | 3.293 (4) | 156.2 |
C1—H1B···O4 | 0.97 | 2.45 | 3.232 (4) | 137.2 |
C2—H2B···O5iii | 0.97 | 2.52 | 3.386 (4) | 149.2 |
C3—H3B···O1ii | 0.97 | 2.44 | 3.308 (4) | 148.0 |
C4—H4A···O5iii | 0.97 | 2.40 | 3.301 (4) | 154.9 |
C5—H5C···O8iv | 0.96 | 2.40 | 3.305 (5) | 156.2 |
C7—H7A···O6v | 0.96 | 2.42 | 3.295 (4) | 151.6 |
C8—H8A···O2iv | 0.96 | 2.50 | 3.355 (5) | 148.5 |
C9—H9A···O2iv | 0.96 | 2.53 | 3.377 (5) | 147.7 |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y−1, z; (iii) x−1, y, z; (iv) x+1, y, z; (v) x−1, y−1, z. |
Acknowledgements
This work was supported by the Tunisian Ministry of H. E. Sc. R.
References
Ben Slimane, A. & Smirani, W. (2008). Z. Kristallogr. New Cryst. Struct. 223, 521–522. CAS Google Scholar
Blessing, R. H. (1986). Acta Cryst. B42, 613–621. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND, Crystal impact GbR, Bonn, Germany. Google Scholar
Brown, I. D. (1976). Acta Cryst. A32, 24–31. CrossRef IUCr Journals Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gatfaoui, S., Marouani, H. & Rzaigui, M. (2013). Acta Cryst. E69, o1453. CSD CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kefi, C., Marouani, H. & Rzaigui, M. (2013). Acta Cryst. E69, o1475. CSD CrossRef IUCr Journals Google Scholar
Marouani, H., Raouafi, N., Toumi Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2012). E-J. Chem. 9, 772–779. CrossRef CAS Google Scholar
Morawitz, T., Lerner, H.-W., Bru Roig, M. & Bolte, M. (2005). Acta Cryst. E61, o4367–o4368. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
1,1,4,7,7-Pentamethyldiethylenetriamine is an amine catalyst primarily used in the production of spray polyurethane foam (SPF). It is classified as tertiary and has basic and nucleophilic properties. In this work, we report the preparation and the structural investigation of a new organic nitrate, C9H26N3(NO3)3.
The asymmetric unit of the title salt consists of three nitrate anions and one 1,1,4,7,7-pentamethylethylenetriammonium trication (Fig. 1). The organic cations are connected to the nitrate anions through multiple bifurcated N—H···O and weak C—H···O hydrogen bonds, with donor-acceptor distances varying between 2.749 (3) and 3.386 (4) Å [d (O···O) > 2.73 Å; Brown, 1976; Blessing, 1986. See Table 1 and Fig. 2).
Nitrate anions are distributed in the (b,c) plane and are interconnected through the organic cations which extend in the direction of the c axis. Geometrical characteristics of the three independent nitrate anions are slightly different. The distance N5—O6 is notably the shortest, 1.204 (3) Å, because O6 is applied in only one hydrogen bond (Table 1) at the same time as N5—O5 distance is much larger, 1.248 (3) Å, because O5 is involved in three hydrogen bonds. These geometrical features have also been noticed in other crystal structures (Marouani et al., 2012; Gatfaoui et al., 2013; Kefi et al., 2013).
Each organic entity is bounded to six different nitrate anions through fifteen N—H···O and C—H···O hydrogen bonds forming a two dimensional network. Examination of the 1,1,4,7,7-pentamethylethylenetriammonium cation shows that the bond distances and angles show no significant difference from those obtained in other structures involving the same organic groups (Morawitz et al., 2005; Ben Slimane & Smirani, 2008). The crystal cohesion and stability are ensured by electrostatic and van der Waals interactions which, together with N—H···O and C—H···O hydrogen bonds, build up a two-dimensional network.